##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'SHELXL97 CIF, edited IUCr template'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2015-08-05
_journal_date_accepted     2015-08-28
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2015
_journal_volume     71
_journal_issue     10
_journal_page_first     1147
_journal_page_last     1150
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989015016163
_journal_coeditor_code     HG5457
_publ_contact_author_name
;
Dr P.A. Crooks
;
_publ_contact_author_address
;
Dept. of Pharm. Sciences
College of Pharmacy
University of Arkansas for Medical Sciences
Little Rock, AR 72205
USA
;
_publ_contact_author_email     'pacrooks@uams.edu'
_publ_contact_author_fax
;
501 686 6057
;
_publ_contact_author_phone
;
501 686 6495
;
_publ_section_title
;
Comparison crystal structure conformations of two structurally related biphenyl
analogues: 4,4'-bis[3-(pyrrolidin-1-yl)prop-1-yn-1-yl]-1,1'-biphenyl and
4,4'-bis{3-[(S)-2-methylpyrrolidin-1-yl]prop-1-yn-1-yl}-1,1'-biphenyl
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Wan, Anqi' .
;
Dept. of Pharm. Sciences
College of Pharmacy
University of Arkansas for Medical Sciences
Little Rock, AR 72205
USA
;
    'Narsimha Reddy Penthala' .
;
Dept. of Pharm. Sciences
College of Pharmacy
University of Arkansas for Medical Sciences
Little Rock, AR 72205
USA
;
    'Fifer, E. Kim' .
;
Dept. of Pharm. Sciences
College of Pharmacy
University of Arkansas for Medical Sciences
Little Rock, AR 72205
USA
;
    'Parkin, Sean' .
;
Dept. of Chemistry
University of Kentucky
Lexington KY 40506
USA
;
    'Crooks, Peter A.' .
;
Dept. of Pharm. Sciences
College of Pharmacy
University of Arkansas for Medical Sciences
Little Rock, AR 72205
USA
;
_publ_section_synopsis
;
The crystal structures of the two title compounds each display the chair
conformation of their piperidine rings. In
4,4'-bis[3-(pyrrolidin-1-yl)prop-1-yn-1-yl]-1,1'-biphenyl, the biphenyl rings
are coplanar because the molecules sit on crystallographic centres of
inversion. In
4,4'-bis{3-[(S)-2-methylpyrrolidin-1-yl]prop-1-yn-1-yl}-1,1'-biphenyl,
the biphenyl ring system has a twisted conformation with a dihedral angle of
28.76 (11)°.
;
data_I
_audit_creation_method     SHELXL-2014/6
_database_code_depnum_ccdc_archive     'CCDC 1421218'
_chemical_name_systematic
;
4,4'-Bis[3-(pyrrolidin-1-yl)prop-1-yn-1-yl]-1,1'-biphenyl
;
_chemical_name_common     ?
_chemical_formula_moiety     'C26 H28 N2'
_chemical_formula_sum     'C26 H28 N2'
_chemical_formula_iupac     'C26 H28 N2'
_chemical_formula_weight     368.50
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     6.21000(10)
_cell_length_b     10.3089(2)
_cell_length_c     16.3082(3)
_cell_angle_alpha     86.3170(10)
_cell_angle_beta     81.2020(10)
_cell_angle_gamma     76.6710(10)
_cell_volume     1003.49(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     9977
_cell_measurement_theta_min     2.74
_cell_measurement_theta_max     68.18
_cell_measurement_temperature     90.0(2)
_exptl_crystal_description     shard
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.230
_exptl_crystal_size_mid     0.190
_exptl_crystal_size_min     0.100
_exptl_crystal_density_diffrn     1.220
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     396
_exptl_absorpt_coefficient_mu     0.538
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_shelx_estimated_absorpt_T_min     0.886
_shelx_estimated_absorpt_T_max     0.948
_exptl_absorpt_correction_T_min     0.811
_exptl_absorpt_correction_T_max     0.929
_diffrn_ambient_temperature     90.0(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_device_type     'Bruker X8 Proteum'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     5.6
_diffrn_reflns_number     13692
_diffrn_reflns_av_R_equivalents     0.0441
_diffrn_reflns_theta_min     2.743
_diffrn_reflns_theta_max     68.202
_diffrn_reflns_theta_full     67.679
_diffrn_measured_fraction_theta_max     0.976
_diffrn_measured_fraction_theta_full     0.979
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     17
_refine_special_details
;
Refinement progress was checked using PLATON (Spek, 2009) and by an
R-tensor (Parkin, 2000). The final model was further checked with the
IUCr utility checkCIF.
;
_reflns_number_total     3586
_reflns_number_gt     3451
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0398
_refine_ls_R_factor_gt     0.0387
_refine_ls_wR_factor_gt     0.1053
_refine_ls_wR_factor_ref     0.1066
_refine_ls_goodness_of_fit_ref     1.031
_refine_ls_restrained_S_all     1.031
_refine_ls_number_reflns     3586
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0577P)²+0.3125P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.222
_refine_diff_density_min     -0.199
_refine_ls_extinction_method
;
SHELXL2014/6 (Sheldrick, 2015)
;
_refine_ls_extinction_coef     0.0061(11)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX2 (Bruker, 2006)
;
_computing_cell_refinement
;
SAINT (Bruker, 2006)
;
_computing_data_reduction
;
SAINT (Bruker, 2006)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014/6 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
XP in SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1A 0.90671(15) 0.09727(9) 0.80861(5) 0.0163(2) Uani d 1 . .
    C C1A 1.11598(18) 0.01531(11) 0.83141(7) 0.0210(3) Uani d 1 . .
    H H1A1 1.2346 0.0010 0.7828 0.025 Uiso calc 1 . .
    H H1A2 1.0951 -0.0723 0.8555 0.025 Uiso calc 1 . .
    C C2A 1.1724(2) 0.09853(12) 0.89584(7) 0.0238(3) Uani d 1 . .
    H H2A1 1.2687 0.1582 0.8692 0.029 Uiso calc 1 . .
    H H2A2 1.2500 0.0406 0.9381 0.029 Uiso calc 1 . .
    C C3A 0.9430(2) 0.17995(12) 0.93527(7) 0.0226(3) Uani d 1 . .
    H H3A1 0.9140 0.1575 0.9953 0.027 Uiso calc 1 . .
    H H3A2 0.9359 0.2769 0.9280 0.027 Uiso calc 1 . .
    C C4A 0.77498(18) 0.13928(11) 0.88842(7) 0.0187(2) Uani d 1 . .
    H H4A1 0.7159 0.0651 0.9180 0.022 Uiso calc 1 . .
    H H4A2 0.6486 0.2155 0.8810 0.022 Uiso calc 1 . .
    C C5A 0.79816(19) 0.02600(11) 0.75852(7) 0.0190(2) Uani d 1 . .
    H H5A1 0.7276 -0.0379 0.7948 0.023 Uiso calc 1 . .
    H H5A2 0.9128 -0.0257 0.7167 0.023 Uiso calc 1 . .
    C C6A 0.62761(18) 0.11598(10) 0.71603(7) 0.0175(2) Uani d 1 . .
    C C7A 0.49421(18) 0.18772(10) 0.67760(6) 0.0168(2) Uani d 1 . .
    C C8A 0.34803(18) 0.27515(10) 0.62731(7) 0.0160(2) Uani d 1 . .
    C C9A 0.43797(18) 0.32491(10) 0.55121(7) 0.0160(2) Uani d 1 . .
    H H9A 0.5942 0.2993 0.5331 0.019 Uiso calc 1 . .
    C C10A 0.30252(18) 0.41090(10) 0.50192(6) 0.0156(2) Uani d 1 . .
    H H10A 0.3677 0.4427 0.4503 0.019 Uiso calc 1 . .
    C C11A 0.07141(17) 0.45231(9) 0.52628(6) 0.0145(2) Uani d 1 . .
    C C12A -0.01727(18) 0.39888(10) 0.60194(7) 0.0177(2) Uani d 1 . .
    H H12A -0.1738 0.4232 0.6197 0.021 Uiso calc 1 . .
    C C13A 0.11676(19) 0.31184(11) 0.65140(7) 0.0182(2) Uani d 1 . .
    H H13A 0.0513 0.2769 0.7020 0.022 Uiso calc 1 . .
    N N1B 0.65099(16) 0.52088(9) 0.86778(6) 0.0188(2) Uani d 1 . .
    C C1B 0.84890(19) 0.56666(12) 0.82796(7) 0.0235(3) Uani d 1 . .
    H H1B1 0.8123 0.6326 0.7824 0.028 Uiso calc 1 . .
    H H1B2 0.9688 0.4911 0.8056 0.028 Uiso calc 1 . .
    C C2B 0.9172(2) 0.63028(13) 0.89876(8) 0.0271(3) Uani d 1 . .
    H H2B1 0.9916 0.7035 0.8777 0.033 Uiso calc 1 . .
    H H2B2 1.0199 0.5635 0.9293 0.033 Uiso calc 1 . .
    C C3B 0.6947(2) 0.68421(12) 0.95488(7) 0.0253(3) Uani d 1 . .
    H H3B1 0.7020 0.6498 1.0127 0.030 Uiso calc 1 . .
    H H3B2 0.6594 0.7829 0.9546 0.030 Uiso calc 1 . .
    C C4B 0.51897(19) 0.63353(11) 0.91723(7) 0.0205(3) Uani d 1 . .
    H H4B1 0.4102 0.6041 0.9612 0.025 Uiso calc 1 . .
    H H4B2 0.4373 0.7036 0.8818 0.025 Uiso calc 1 . .
    C C5B 0.52980(19) 0.47407(11) 0.80985(7) 0.0204(3) Uani d 1 . .
    H H5B1 0.4064 0.4386 0.8422 0.024 Uiso calc 1 . .
    H H5B2 0.6326 0.3993 0.7790 0.024 Uiso calc 1 . .
    C C6B 0.43522(19) 0.57591(11) 0.74928(7) 0.0199(3) Uani d 1 . .
    C C7B 0.35385(19) 0.66217(11) 0.70308(7) 0.0190(3) Uani d 1 . .
    C C8B 0.25131(18) 0.76103(10) 0.64637(6) 0.0170(2) Uani d 1 . .
    C C9B 0.06171(19) 0.74642(11) 0.61458(7) 0.0180(2) Uani d 1 . .
    H H9B -0.0018 0.6720 0.6322 0.022 Uiso calc 1 . .
    C C10B -0.03435(18) 0.83874(10) 0.55795(7) 0.0173(2) Uani d 1 . .
    H H10B -0.1620 0.8259 0.5369 0.021 Uiso calc 1 . .
    C C11B 0.05162(17) 0.95096(10) 0.53077(6) 0.0155(2) Uani d 1 . .
    C C12B 0.23930(18) 0.96591(10) 0.56433(7) 0.0175(2) Uani d 1 . .
    H H12B 0.3002 1.0417 0.5481 0.021 Uiso calc 1 . .
    C C13B 0.33793(18) 0.87324(11) 0.62041(7) 0.0180(2) Uani d 1 . .
    H H13B 0.4658 0.8858 0.6415 0.022 Uiso calc 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N1A C4A . 1.4609(13) ?
    N1A C5A . 1.4612(13) ?
    N1A C1A . 1.4637(14) ?
    C1A C2A . 1.5264(15) ?
    C1A H1A1 . 0.9900 ?
    C1A H1A2 . 0.9900 ?
    C2A C3A . 1.5442(16) ?
    C2A H2A1 . 0.9900 ?
    C2A H2A2 . 0.9900 ?
    C3A C4A . 1.5283(15) ?
    C3A H3A1 . 0.9900 ?
    C3A H3A2 . 0.9900 ?
    C4A H4A1 . 0.9900 ?
    C4A H4A2 . 0.9900 ?
    C5A C6A . 1.4667(15) ?
    C5A H5A1 . 0.9900 ?
    C5A H5A2 . 0.9900 ?
    C6A C7A . 1.2012(16) ?
    C7A C8A . 1.4369(15) ?
    C8A C9A . 1.3976(15) ?
    C8A C13A . 1.3986(16) ?
    C9A C10A . 1.3825(15) ?
    C9A H9A . 0.9500 ?
    C10A C11A . 1.4017(15) ?
    C10A H10A . 0.9500 ?
    C11A C12A . 1.4049(15) ?
    C11A C11A 2_566 1.487(2) ?
    C12A C13A . 1.3844(15) ?
    C12A H12A . 0.9500 ?
    C13A H13A . 0.9500 ?
    N1B C5B . 1.4613(14) ?
    N1B C1B . 1.4625(15) ?
    N1B C4B . 1.4663(14) ?
    C1B C2B . 1.5228(16) ?
    C1B H1B1 . 0.9900 ?
    C1B H1B2 . 0.9900 ?
    C2B C3B . 1.5430(17) ?
    C2B H2B1 . 0.9900 ?
    C2B H2B2 . 0.9900 ?
    C3B C4B . 1.5329(16) ?
    C3B H3B1 . 0.9900 ?
    C3B H3B2 . 0.9900 ?
    C4B H4B1 . 0.9900 ?
    C4B H4B2 . 0.9900 ?
    C5B C6B . 1.4775(15) ?
    C5B H5B1 . 0.9900 ?
    C5B H5B2 . 0.9900 ?
    C6B C7B . 1.1987(16) ?
    C7B C8B . 1.4350(15) ?
    C8B C9B . 1.3986(16) ?
    C8B C13B . 1.4003(16) ?
    C9B C10B . 1.3815(15) ?
    C9B H9B . 0.9500 ?
    C10B C11B . 1.4023(15) ?
    C10B H10B . 0.9500 ?
    C11B C12B . 1.4037(15) ?
    C11B C11B 2_576 1.486(2) ?
    C12B C13B . 1.3834(15) ?
    C12B H12B . 0.9500 ?
    C13B H13B . 0.9500 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C4A N1A C5A . . 114.19(9) ?
    C4A N1A C1A . . 103.63(8) ?
    C5A N1A C1A . . 112.60(8) ?
    N1A C1A C2A . . 102.99(9) ?
    N1A C1A H1A1 . . 111.2 ?
    C2A C1A H1A1 . . 111.2 ?
    N1A C1A H1A2 . . 111.2 ?
    C2A C1A H1A2 . . 111.2 ?
    H1A1 C1A H1A2 . . 109.1 ?
    C1A C2A C3A . . 104.25(9) ?
    C1A C2A H2A1 . . 110.9 ?
    C3A C2A H2A1 . . 110.9 ?
    C1A C2A H2A2 . . 110.9 ?
    C3A C2A H2A2 . . 110.9 ?
    H2A1 C2A H2A2 . . 108.9 ?
    C4A C3A C2A . . 104.34(9) ?
    C4A C3A H3A1 . . 110.9 ?
    C2A C3A H3A1 . . 110.9 ?
    C4A C3A H3A2 . . 110.9 ?
    C2A C3A H3A2 . . 110.9 ?
    H3A1 C3A H3A2 . . 108.9 ?
    N1A C4A C3A . . 103.36(9) ?
    N1A C4A H4A1 . . 111.1 ?
    C3A C4A H4A1 . . 111.1 ?
    N1A C4A H4A2 . . 111.1 ?
    C3A C4A H4A2 . . 111.1 ?
    H4A1 C4A H4A2 . . 109.1 ?
    N1A C5A C6A . . 112.54(8) ?
    N1A C5A H5A1 . . 109.1 ?
    C6A C5A H5A1 . . 109.1 ?
    N1A C5A H5A2 . . 109.1 ?
    C6A C5A H5A2 . . 109.1 ?
    H5A1 C5A H5A2 . . 107.8 ?
    C7A C6A C5A . . 176.79(11) ?
    C6A C7A C8A . . 175.84(11) ?
    C9A C8A C13A . . 118.34(10) ?
    C9A C8A C7A . . 119.38(10) ?
    C13A C8A C7A . . 122.28(10) ?
    C10A C9A C8A . . 120.86(10) ?
    C10A C9A H9A . . 119.6 ?
    C8A C9A H9A . . 119.6 ?
    C9A C10A C11A . . 121.62(10) ?
    C9A C10A H10A . . 119.2 ?
    C11A C10A H10A . . 119.2 ?
    C10A C11A C12A . . 116.84(10) ?
    C10A C11A C11A . 2_566 121.06(12) ?
    C12A C11A C11A . 2_566 122.10(12) ?
    C13A C12A C11A . . 121.94(10) ?
    C13A C12A H12A . . 119.0 ?
    C11A C12A H12A . . 119.0 ?
    C12A C13A C8A . . 120.35(10) ?
    C12A C13A H13A . . 119.8 ?
    C8A C13A H13A . . 119.8 ?
    C5B N1B C1B . . 114.00(9) ?
    C5B N1B C4B . . 114.41(9) ?
    C1B N1B C4B . . 104.43(9) ?
    N1B C1B C2B . . 102.86(9) ?
    N1B C1B H1B1 . . 111.2 ?
    C2B C1B H1B1 . . 111.2 ?
    N1B C1B H1B2 . . 111.2 ?
    C2B C1B H1B2 . . 111.2 ?
    H1B1 C1B H1B2 . . 109.1 ?
    C1B C2B C3B . . 104.18(9) ?
    C1B C2B H2B1 . . 110.9 ?
    C3B C2B H2B1 . . 110.9 ?
    C1B C2B H2B2 . . 110.9 ?
    C3B C2B H2B2 . . 110.9 ?
    H2B1 C2B H2B2 . . 108.9 ?
    C4B C3B C2B . . 104.86(9) ?
    C4B C3B H3B1 . . 110.8 ?
    C2B C3B H3B1 . . 110.8 ?
    C4B C3B H3B2 . . 110.8 ?
    C2B C3B H3B2 . . 110.8 ?
    H3B1 C3B H3B2 . . 108.9 ?
    N1B C4B C3B . . 103.67(9) ?
    N1B C4B H4B1 . . 111.0 ?
    C3B C4B H4B1 . . 111.0 ?
    N1B C4B H4B2 . . 111.0 ?
    C3B C4B H4B2 . . 111.0 ?
    H4B1 C4B H4B2 . . 109.0 ?
    N1B C5B C6B . . 115.14(9) ?
    N1B C5B H5B1 . . 108.5 ?
    C6B C5B H5B1 . . 108.5 ?
    N1B C5B H5B2 . . 108.5 ?
    C6B C5B H5B2 . . 108.5 ?
    H5B1 C5B H5B2 . . 107.5 ?
    C7B C6B C5B . . 177.04(11) ?
    C6B C7B C8B . . 177.29(11) ?
    C9B C8B C13B . . 118.07(10) ?
    C9B C8B C7B . . 120.32(10) ?
    C13B C8B C7B . . 121.61(10) ?
    C10B C9B C8B . . 120.86(10) ?
    C10B C9B H9B . . 119.6 ?
    C8B C9B H9B . . 119.6 ?
    C9B C10B C11B . . 121.74(10) ?
    C9B C10B H10B . . 119.1 ?
    C11B C10B H10B . . 119.1 ?
    C10B C11B C12B . . 116.87(10) ?
    C10B C11B C11B . 2_576 121.34(12) ?
    C12B C11B C11B . 2_576 121.79(11) ?
    C13B C12B C11B . . 121.76(10) ?
    C13B C12B H12B . . 119.1 ?
    C11B C12B H12B . . 119.1 ?
    C12B C13B C8B . . 120.68(10) ?
    C12B C13B H13B . . 119.7 ?
    C8B C13B H13B . . 119.7 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C4A N1A C1A C2A . . . . -45.38(10) ?
    C5A N1A C1A C2A . . . . -169.28(9) ?
    N1A C1A C2A C3A . . . . 27.96(11) ?
    C1A C2A C3A C4A . . . . -1.49(11) ?
    C5A N1A C4A C3A . . . . 167.28(9) ?
    C1A N1A C4A C3A . . . . 44.43(10) ?
    C2A C3A C4A N1A . . . . -25.57(11) ?
    C4A N1A C5A C6A . . . . 78.62(11) ?
    C1A N1A C5A C6A . . . . -163.55(9) ?
    C13A C8A C9A C10A . . . . 1.59(15) ?
    C7A C8A C9A C10A . . . . -178.97(9) ?
    C8A C9A C10A C11A . . . . 0.51(15) ?
    C9A C10A C11A C12A . . . . -2.01(14) ?
    C9A C10A C11A C11A . . . 2_566 178.33(10) ?
    C10A C11A C12A C13A . . . . 1.47(15) ?
    C11A C11A C12A C13A 2_566 . . . -178.88(11) ?
    C11A C12A C13A C8A . . . . 0.58(16) ?
    C9A C8A C13A C12A . . . . -2.12(15) ?
    C7A C8A C13A C12A . . . . 178.46(9) ?
    C5B N1B C1B C2B . . . . 170.74(9) ?
    C4B N1B C1B C2B . . . . 45.18(11) ?
    N1B C1B C2B C3B . . . . -30.78(12) ?
    C1B C2B C3B C4B . . . . 6.22(12) ?
    C5B N1B C4B C3B . . . . -166.33(9) ?
    C1B N1B C4B C3B . . . . -41.02(11) ?
    C2B C3B C4B N1B . . . . 20.48(12) ?
    C1B N1B C5B C6B . . . . -62.66(13) ?
    C4B N1B C5B C6B . . . . 57.45(13) ?
    C13B C8B C9B C10B . . . . 1.28(15) ?
    C7B C8B C9B C10B . . . . -177.95(9) ?
    C8B C9B C10B C11B . . . . -0.73(16) ?
    C9B C10B C11B C12B . . . . -0.51(15) ?
    C9B C10B C11B C11B . . . 2_576 179.42(11) ?
    C10B C11B C12B C13B . . . . 1.19(15) ?
    C11B C11B C12B C13B 2_576 . . . -178.74(11) ?
    C11B C12B C13B C8B . . . . -0.65(16) ?
    C9B C8B C13B C12B . . . . -0.60(15) ?
    C7B C8B C13B C12B . . . . 178.61(9) ?
_shelxl_version_number     2014/6
data_II
_audit_creation_method     SHELXL-2014/6
_database_code_depnum_ccdc_archive     'CCDC 1421219'
_chemical_name_systematic
;
4,4'-Bis{3-[(S)-2-methylpyrrolidin-1-yl]prop-1-yn-1-yl}-1,1'-biphenyl
;
_chemical_name_common     ?
_chemical_formula_moiety     'C28 H32 N2'
_chemical_formula_sum     'C28 H32 N2'
_chemical_formula_iupac     'C28 H32 N2'
_chemical_formula_weight     396.55
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21'
_space_group_name_Hall     'P 2yb'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     8.1411(4)
_cell_length_b     7.3080(4)
_cell_length_c     18.9840(9)
_cell_angle_alpha     90
_cell_angle_beta     98.177(3)
_cell_angle_gamma     90
_cell_volume     1117.97(10)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2730
_cell_measurement_theta_min     1.00
_cell_measurement_theta_max     27.48
_cell_measurement_temperature     90.0(2)
_exptl_crystal_description     'cut slab'
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.410
_exptl_crystal_size_mid     0.350
_exptl_crystal_size_min     0.075
_exptl_crystal_density_diffrn     1.178
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     428
_exptl_absorpt_coefficient_mu     0.068
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_shelx_estimated_absorpt_T_min     0.973
_shelx_estimated_absorpt_T_max     0.995
_exptl_absorpt_correction_T_min     0.791
_exptl_absorpt_correction_T_max     0.971
_diffrn_ambient_temperature     90.0(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Nonius KappaCCD diffractometer'
_diffrn_measurement_method     'φ and ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean     9.1
_diffrn_reflns_number     15874
_diffrn_reflns_av_R_equivalents     0.0850
_diffrn_reflns_theta_min     2.168
_diffrn_reflns_theta_max     27.497
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_limit_l_max     24
_refine_special_details
;
Refinement progress was checked using PLATON (Spek, 2009) and by an
R-tensor (Parkin, 2000). The final model was further checked with the
IUCr utility checkCIF.
Absolute structure analysis:
The Flack x parameter was determined using 1205 quotients of the form
[(I+)-(I-)]/[(I+)+(I-)], but since the anomalous signal was so small the
result is thoroughly inconclusive.  This is to be expected, and merely
confirms what we already know about light atom non-centrosymmetric
structures that are determined with MoKα radiation.  The quotient
method has been described by Parsons et al. (2013).  However,
the synthesis used pure (S)-2-methylpyrrolidine, so the absolute
configuration for the model of (II) was dictated by the synthesis.
;
_reflns_number_total     4705
_reflns_number_gt     3548
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0813
_refine_ls_R_factor_gt     0.0543
_refine_ls_wR_factor_gt     0.1278
_refine_ls_wR_factor_ref     0.1442
_refine_ls_goodness_of_fit_ref     1.045
_refine_ls_restrained_S_all     1.045
_refine_ls_number_reflns     4705
_refine_ls_number_parameters     273
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0742P)²+0.0409P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.299
_refine_diff_density_min     -0.192
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack x parameter was determined using 1205 quotients of the form
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack     -0.3(10)
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
COLLECT (Nonius, 1998)
;
_computing_cell_refinement
;
SCALEPACK (Otwinowski & Minor, 2006)
;
_computing_data_reduction
;
DENZO-SMN (Otwinowski & Minor, 2006)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
XP in SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELX (Sheldrick, 2008) and CIFFIX (Parkin, 2013)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    N N1 -0.0921(3) 0.5633(4) 0.18120(12) 0.0294(6) Uani d 1 . .
    N N2 1.5991(3) 0.4631(4) 0.82088(11) 0.0288(6) Uani d 1 . .
    C C1 -0.0274(4) 0.7478(5) 0.17326(15) 0.0333(7) Uani d 1 . .
    H H1A 0.0846 0.7619 0.2008 0.040 Uiso calc 1 . .
    H H1B -0.1021 0.8413 0.1892 0.040 Uiso calc 1 . .
    C C2 -0.0213(4) 0.7632(5) 0.09382(16) 0.0384(8) Uani d 1 . .
    H H2A 0.0767 0.8345 0.0845 0.046 Uiso calc 1 . .
    H H2B -0.1229 0.8226 0.0692 0.046 Uiso calc 1 . .
    C C3 -0.0094(4) 0.5640(5) 0.06935(15) 0.0381(8) Uani d 1 . .
    H H3A -0.1085 0.5300 0.0354 0.046 Uiso calc 1 . .
    H H3B 0.0907 0.5459 0.0460 0.046 Uiso calc 1 . .
    C C4 0.0011(3) 0.4496(5) 0.13712(15) 0.0327(7) Uani d 1 . .
    H H4A 0.1195 0.4424 0.1599 0.039 Uiso calc 1 . .
    C C5 -0.0680(5) 0.2582(6) 0.12600(18) 0.0533(10) Uani d 1 . .
    H H5A -0.0562 0.1938 0.1717 0.080 Uiso calc 1 . .
    H H5B -0.0069 0.1920 0.0931 0.080 Uiso calc 1 . .
    H H5C -0.1857 0.2647 0.1060 0.080 Uiso calc 1 . .
    C C6 -0.0833(3) 0.5055(5) 0.25511(14) 0.0336(8) Uani d 1 . .
    H H6A -0.1321 0.3816 0.2560 0.040 Uiso calc 1 . .
    H H6B -0.1527 0.5892 0.2794 0.040 Uiso calc 1 . .
    C C7 0.0854(3) 0.5015(4) 0.29597(14) 0.0296(7) Uani d 1 . .
    C C8 0.2237(3) 0.5035(4) 0.32840(13) 0.0258(6) Uani d 1 . .
    C C9 0.3832(3) 0.5132(4) 0.37271(13) 0.0251(6) Uani d 1 . .
    C C10 0.5206(3) 0.4133(4) 0.35812(14) 0.0263(6) Uani d 1 . .
    H H10A 0.5128 0.3411 0.3162 0.032 Uiso calc 1 . .
    C C11 0.6689(3) 0.4188(4) 0.40464(13) 0.0249(6) Uani d 1 . .
    H H11A 0.7614 0.3508 0.3937 0.030 Uiso calc 1 . .
    C C12 0.6847(3) 0.5219(4) 0.46694(13) 0.0243(6) Uani d 1 . .
    C C13 0.5480(3) 0.6270(4) 0.47988(14) 0.0254(6) Uani d 1 . .
    H H13A 0.5569 0.7026 0.5210 0.030 Uiso calc 1 . .
    C C14 0.4002(3) 0.6225(4) 0.43367(13) 0.0257(6) Uani d 1 . .
    H H14A 0.3091 0.6947 0.4436 0.031 Uiso calc 1 . .
    C C15 0.8386(3) 0.5167(4) 0.51885(13) 0.0239(6) Uani d 1 . .
    C C16 0.9931(4) 0.4757(4) 0.49786(15) 0.0261(6) Uani d 1 . .
    H H16A 1.0010 0.4593 0.4488 0.031 Uiso calc 1 . .
    C C17 1.1338(3) 0.4589(4) 0.54754(14) 0.0271(7) Uani d 1 . .
    H H17A 1.2369 0.4320 0.5319 0.033 Uiso calc 1 . .
    C C18 1.1278(3) 0.4805(4) 0.61967(13) 0.0247(6) Uani d 1 . .
    C C19 0.9756(3) 0.5261(4) 0.64146(14) 0.0276(7) Uani d 1 . .
    H H19A 0.9690 0.5456 0.6905 0.033 Uiso calc 1 . .
    C C20 0.8343(3) 0.5429(4) 0.59141(14) 0.0271(7) Uani d 1 . .
    H H20A 0.7319 0.5731 0.6070 0.033 Uiso calc 1 . .
    C C21 1.2782(3) 0.4600(5) 0.66923(13) 0.0287(7) Uani d 1 . .
    C C22 1.4103(3) 0.4380(5) 0.70559(14) 0.0318(7) Uani d 1 . .
    C C23 1.5765(3) 0.4087(6) 0.74681(14) 0.0388(9) Uani d 1 . .
    H H23A 1.6034 0.2769 0.7446 0.047 Uiso calc 1 . .
    H H23B 1.6583 0.4760 0.7228 0.047 Uiso calc 1 . .
    C C24 1.5747(4) 0.6593(5) 0.83087(16) 0.0364(7) Uani d 1 . .
    H H24A 1.4666 0.7004 0.8053 0.044 Uiso calc 1 . .
    H H24B 1.6646 0.7315 0.8142 0.044 Uiso calc 1 . .
    C C25 1.5796(5) 0.6761(6) 0.91101(17) 0.0487(10) Uani d 1 . .
    H H25A 1.5039 0.7738 0.9229 0.058 Uiso calc 1 . .
    H H25B 1.6934 0.7034 0.9346 0.058 Uiso calc 1 . .
    C C26 1.5222(4) 0.4886(6) 0.93362(15) 0.0439(9) Uani d 1 . .
    H H26A 1.6096 0.4298 0.9678 0.053 Uiso calc 1 . .
    H H26B 1.4204 0.5003 0.9563 0.053 Uiso calc 1 . .
    C C27 1.4879(4) 0.3770(5) 0.86523(16) 0.0347(8) Uani d 1 . .
    H H27A 1.3706 0.3987 0.8431 0.042 Uiso calc 1 . .
    C C28 1.5151(4) 0.1744(5) 0.8746(2) 0.0535(10) Uani d 1 . .
    H H28A 1.4918 0.1137 0.8282 0.080 Uiso calc 1 . .
    H H28C 1.4408 0.1262 0.9064 0.080 Uiso calc 1 . .
    H H28D 1.6306 0.1513 0.8952 0.080 Uiso calc 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    N1 C6 . 1.457(4) ?
    N1 C1 . 1.463(4) ?
    N1 C4 . 1.465(4) ?
    N2 C23 . 1.448(3) ?
    N2 C27 . 1.463(4) ?
    N2 C24 . 1.464(4) ?
    C1 C2 . 1.520(4) ?
    C1 H1A . 0.9900 ?
    C1 H1B . 0.9900 ?
    C2 C3 . 1.536(5) ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C3 C4 . 1.526(4) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 C5 . 1.511(5) ?
    C4 H4A . 1.0000 ?
    C5 H5A . 0.9800 ?
    C5 H5B . 0.9800 ?
    C5 H5C . 0.9800 ?
    C6 C7 . 1.479(4) ?
    C6 H6A . 0.9900 ?
    C6 H6B . 0.9900 ?
    C7 C8 . 1.204(3) ?
    C8 C9 . 1.445(3) ?
    C9 C10 . 1.396(4) ?
    C9 C14 . 1.397(4) ?
    C10 C11 . 1.391(3) ?
    C10 H10A . 0.9500 ?
    C11 C12 . 1.393(4) ?
    C11 H11A . 0.9500 ?
    C12 C13 . 1.403(4) ?
    C12 C15 . 1.480(3) ?
    C13 C14 . 1.385(3) ?
    C13 H13A . 0.9500 ?
    C14 H14A . 0.9500 ?
    C15 C20 . 1.396(4) ?
    C15 C16 . 1.405(4) ?
    C16 C17 . 1.381(4) ?
    C16 H16A . 0.9500 ?
    C17 C18 . 1.386(4) ?
    C17 H17A . 0.9500 ?
    C18 C19 . 1.401(4) ?
    C18 C21 . 1.442(3) ?
    C19 C20 . 1.389(4) ?
    C19 H19A . 0.9500 ?
    C20 H20A . 0.9500 ?
    C21 C22 . 1.203(4) ?
    C22 C23 . 1.479(4) ?
    C23 H23A . 0.9900 ?
    C23 H23B . 0.9900 ?
    C24 C25 . 1.521(4) ?
    C24 H24A . 0.9900 ?
    C24 H24B . 0.9900 ?
    C25 C26 . 1.529(6) ?
    C25 H25A . 0.9900 ?
    C25 H25B . 0.9900 ?
    C26 C27 . 1.525(5) ?
    C26 H26A . 0.9900 ?
    C26 H26B . 0.9900 ?
    C27 C28 . 1.504(5) ?
    C27 H27A . 1.0000 ?
    C28 H28A . 0.9800 ?
    C28 H28C . 0.9800 ?
    C28 H28D . 0.9800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C6 N1 C1 . . 113.4(2) ?
    C6 N1 C4 . . 115.3(2) ?
    C1 N1 C4 . . 103.9(2) ?
    C23 N2 C27 . . 115.9(2) ?
    C23 N2 C24 . . 113.2(3) ?
    C27 N2 C24 . . 103.9(2) ?
    N1 C1 C2 . . 103.5(2) ?
    N1 C1 H1A . . 111.1 ?
    C2 C1 H1A . . 111.1 ?
    N1 C1 H1B . . 111.1 ?
    C2 C1 H1B . . 111.1 ?
    H1A C1 H1B . . 109.0 ?
    C1 C2 C3 . . 104.0(3) ?
    C1 C2 H2A . . 111.0 ?
    C3 C2 H2A . . 111.0 ?
    C1 C2 H2B . . 111.0 ?
    C3 C2 H2B . . 111.0 ?
    H2A C2 H2B . . 109.0 ?
    C4 C3 C2 . . 105.2(3) ?
    C4 C3 H3A . . 110.7 ?
    C2 C3 H3A . . 110.7 ?
    C4 C3 H3B . . 110.7 ?
    C2 C3 H3B . . 110.7 ?
    H3A C3 H3B . . 108.8 ?
    N1 C4 C5 . . 113.1(3) ?
    N1 C4 C3 . . 101.5(3) ?
    C5 C4 C3 . . 114.5(3) ?
    N1 C4 H4A . . 109.2 ?
    C5 C4 H4A . . 109.2 ?
    C3 C4 H4A . . 109.2 ?
    C4 C5 H5A . . 109.5 ?
    C4 C5 H5B . . 109.5 ?
    H5A C5 H5B . . 109.5 ?
    C4 C5 H5C . . 109.5 ?
    H5A C5 H5C . . 109.5 ?
    H5B C5 H5C . . 109.5 ?
    N1 C6 C7 . . 115.2(2) ?
    N1 C6 H6A . . 108.5 ?
    C7 C6 H6A . . 108.5 ?
    N1 C6 H6B . . 108.5 ?
    C7 C6 H6B . . 108.5 ?
    H6A C6 H6B . . 107.5 ?
    C8 C7 C6 . . 177.9(3) ?
    C7 C8 C9 . . 174.7(3) ?
    C10 C9 C14 . . 118.4(2) ?
    C10 C9 C8 . . 122.5(2) ?
    C14 C9 C8 . . 119.0(2) ?
    C11 C10 C9 . . 120.4(2) ?
    C11 C10 H10A . . 119.8 ?
    C9 C10 H10A . . 119.8 ?
    C10 C11 C12 . . 121.5(3) ?
    C10 C11 H11A . . 119.3 ?
    C12 C11 H11A . . 119.3 ?
    C11 C12 C13 . . 117.7(2) ?
    C11 C12 C15 . . 121.3(2) ?
    C13 C12 C15 . . 121.0(2) ?
    C14 C13 C12 . . 121.0(2) ?
    C14 C13 H13A . . 119.5 ?
    C12 C13 H13A . . 119.5 ?
    C13 C14 C9 . . 120.8(2) ?
    C13 C14 H14A . . 119.6 ?
    C9 C14 H14A . . 119.6 ?
    C20 C15 C16 . . 117.2(2) ?
    C20 C15 C12 . . 121.1(2) ?
    C16 C15 C12 . . 121.6(2) ?
    C17 C16 C15 . . 120.9(2) ?
    C17 C16 H16A . . 119.5 ?
    C15 C16 H16A . . 119.5 ?
    C16 C17 C18 . . 121.5(2) ?
    C16 C17 H17A . . 119.3 ?
    C18 C17 H17A . . 119.3 ?
    C17 C18 C19 . . 118.4(2) ?
    C17 C18 C21 . . 119.1(2) ?
    C19 C18 C21 . . 122.4(2) ?
    C20 C19 C18 . . 120.0(2) ?
    C20 C19 H19A . . 120.0 ?
    C18 C19 H19A . . 120.0 ?
    C19 C20 C15 . . 121.9(2) ?
    C19 C20 H20A . . 119.0 ?
    C15 C20 H20A . . 119.0 ?
    C22 C21 C18 . . 174.2(3) ?
    C21 C22 C23 . . 177.0(3) ?
    N2 C23 C22 . . 117.0(2) ?
    N2 C23 H23A . . 108.0 ?
    C22 C23 H23A . . 108.0 ?
    N2 C23 H23B . . 108.0 ?
    C22 C23 H23B . . 108.0 ?
    H23A C23 H23B . . 107.3 ?
    N2 C24 C25 . . 102.9(3) ?
    N2 C24 H24A . . 111.2 ?
    C25 C24 H24A . . 111.2 ?
    N2 C24 H24B . . 111.2 ?
    C25 C24 H24B . . 111.2 ?
    H24A C24 H24B . . 109.1 ?
    C24 C25 C26 . . 104.1(3) ?
    C24 C25 H25A . . 110.9 ?
    C26 C25 H25A . . 110.9 ?
    C24 C25 H25B . . 110.9 ?
    C26 C25 H25B . . 110.9 ?
    H25A C25 H25B . . 109.0 ?
    C27 C26 C25 . . 105.5(2) ?
    C27 C26 H26A . . 110.7 ?
    C25 C26 H26A . . 110.7 ?
    C27 C26 H26B . . 110.7 ?
    C25 C26 H26B . . 110.7 ?
    H26A C26 H26B . . 108.8 ?
    N2 C27 C28 . . 113.5(3) ?
    N2 C27 C26 . . 101.9(3) ?
    C28 C27 C26 . . 114.8(3) ?
    N2 C27 H27A . . 108.8 ?
    C28 C27 H27A . . 108.8 ?
    C26 C27 H27A . . 108.8 ?
    C27 C28 H28A . . 109.5 ?
    C27 C28 H28C . . 109.5 ?
    H28A C28 H28C . . 109.5 ?
    C27 C28 H28D . . 109.5 ?
    H28A C28 H28D . . 109.5 ?
    H28C C28 H28D . . 109.5 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 N1 C1 C2 . . . . 170.4(2) ?
    C4 N1 C1 C2 . . . . 44.5(3) ?
    N1 C1 C2 C3 . . . . -24.3(3) ?
    C1 C2 C3 C4 . . . . -3.3(3) ?
    C6 N1 C4 C5 . . . . 66.3(3) ?
    C1 N1 C4 C5 . . . . -169.0(3) ?
    C6 N1 C4 C3 . . . . -170.6(2) ?
    C1 N1 C4 C3 . . . . -45.9(3) ?
    C2 C3 C4 N1 . . . . 29.5(3) ?
    C2 C3 C4 C5 . . . . 151.6(3) ?
    C1 N1 C6 C7 . . . . -59.8(3) ?
    C4 N1 C6 C7 . . . . 59.8(4) ?
    C14 C9 C10 C11 . . . . 2.0(4) ?
    C8 C9 C10 C11 . . . . -176.2(3) ?
    C9 C10 C11 C12 . . . . 0.5(4) ?
    C10 C11 C12 C13 . . . . -2.8(4) ?
    C10 C11 C12 C15 . . . . 175.5(2) ?
    C11 C12 C13 C14 . . . . 2.6(4) ?
    C15 C12 C13 C14 . . . . -175.7(3) ?
    C12 C13 C14 C9 . . . . -0.1(4) ?
    C10 C9 C14 C13 . . . . -2.2(4) ?
    C8 C9 C14 C13 . . . . 176.1(3) ?
    C11 C12 C15 C20 . . . . -149.7(3) ?
    C13 C12 C15 C20 . . . . 28.5(4) ?
    C11 C12 C15 C16 . . . . 26.8(4) ?
    C13 C12 C15 C16 . . . . -155.0(3) ?
    C20 C15 C16 C17 . . . . 1.2(4) ?
    C12 C15 C16 C17 . . . . -175.5(3) ?
    C15 C16 C17 C18 . . . . 0.4(4) ?
    C16 C17 C18 C19 . . . . -2.1(4) ?
    C16 C17 C18 C21 . . . . 179.5(3) ?
    C17 C18 C19 C20 . . . . 2.0(4) ?
    C21 C18 C19 C20 . . . . -179.6(3) ?
    C18 C19 C20 C15 . . . . -0.4(4) ?
    C16 C15 C20 C19 . . . . -1.2(4) ?
    C12 C15 C20 C19 . . . . 175.5(3) ?
    C27 N2 C23 C22 . . . . 57.8(4) ?
    C24 N2 C23 C22 . . . . -62.1(4) ?
    C23 N2 C24 C25 . . . . 172.0(2) ?
    C27 N2 C24 C25 . . . . 45.4(3) ?
    N2 C24 C25 C26 . . . . -26.8(3) ?
    C24 C25 C26 C27 . . . . -0.1(3) ?
    C23 N2 C27 C28 . . . . 66.2(3) ?
    C24 N2 C27 C28 . . . . -169.0(2) ?
    C23 N2 C27 C26 . . . . -169.8(3) ?
    C24 N2 C27 C26 . . . . -44.9(3) ?
    C25 C26 C27 N2 . . . . 26.9(3) ?
    C25 C26 C27 C28 . . . . 150.0(3) ?
_shelxl_version_number     2014/6
