##############################################################################
#                                                                            #
# 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     SHELXL-97
_journal_date_recd_electronic     2013-03-09
_journal_date_accepted     2013-07-10
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue      8
_journal_page_first     o1286
_journal_page_last     o1287
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536813019168
_journal_coeditor_code     GG2114
_publ_contact_author_name     'Urmila H. Patel'
_publ_contact_author_address
;
Department of Physics
Sardar Patel University
Vallabh Vidya Nagar
Gujarat 388 120
India
;
_publ_contact_author_email     'u_h_patel@yahoo.com'
_publ_contact_author_fax     '091-2692-236475'
_publ_contact_author_phone     '091-2692-226843'
_publ_section_title
;\
5-(4-Chlorophenyl)-7-(4-methylphenyl)-4-(pyrrolidin-1-yl)-7H-pyrrolo[2,\
3-d]pyrimidine
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Patel, Urmila H.' .
;
Department of Physics
Sardar Patel University
Vallabh Vidya Nagar
Gujarat 388 120
India
;
    'Modh, Rajesh D.' .
;
Department of Physics
Sardar Patel University
Vallabh Vidya Nagar
Gujarat 388 120
India
;
    'Shah, Dhaval A.' .
;
Organic Syntheses Laboratory,
M. G. Science Institute, Navarangpura,
Ahmedabad 380 009, India
;
data_I
_chemical_name_systematic
;\
5-(4-Chlorophenyl)-7-(4-methylphenyl)-4-(pyrrolidin-1-yl)-\
7H-pyrrolo[2,3-d]pyrimidine
;
_chemical_name_common     ?
_chemical_formula_moiety     'C23 H21 Cl N4'
_chemical_formula_sum     'C23 H21 Cl N4'
_chemical_formula_iupac     'C23 H21 Cl N4'
_chemical_formula_weight     388.72
_chemical_melting_point     433
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.967(3)
_cell_length_b     15.367(5)
_cell_length_c     15.960(2)
_cell_angle_alpha     69.210(17)
_cell_angle_beta     75.653(16)
_cell_angle_gamma     76.52(3)
_cell_volume     1966.2(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     10
_cell_measurement_theta_max     25
_cell_measurement_temperature     293(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     'White'
_exptl_crystal_size_max     0.3
_exptl_crystal_size_mid     0.2
_exptl_crystal_size_min     0.2
_exptl_crystal_density_diffrn     1.313
_exptl_crystal_density_meas     1.310
_exptl_crystal_density_method     'floatation method'
_exptl_crystal_F_000     816
_exptl_absorpt_coefficient_mu     0.210
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North et al., 1968)'
_exptl_absorpt_correction_T_min     0.951
_exptl_absorpt_correction_T_max     0.959
_exptl_special_details     ?
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Enraf--Nonius CAD-4'
_diffrn_measurement_method     'ω-2θ'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7458
_diffrn_reflns_av_R_equivalents     0.0271
_diffrn_reflns_av_sigmaI/netI     0.0652
_diffrn_reflns_theta_min     2.29
_diffrn_reflns_theta_max     24.98
_diffrn_reflns_theta_full     24.98
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     2
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     1
_diffrn_standards_decay_%     0
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     6909
_reflns_number_gt     3569
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1223
_refine_ls_R_factor_gt     0.0418
_refine_ls_wR_factor_gt     0.0991
_refine_ls_wR_factor_ref     0.1249
_refine_ls_goodness_of_fit_ref     1.007
_refine_ls_restrained_S_all     1.007
_refine_ls_number_reflns     6864
_refine_ls_number_parameters     507
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
               'w=1/[σ²(Fo²)+(0.0544P)²+0.227P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.178
_refine_diff_density_min     -0.249
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_cell_refinement     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2009)'
_computing_publication_material     'publCIF (Westrip, 2010)'
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_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C2 0.2724(3) 0.05271(17) 0.38941(16) 0.0460(7) Uani d . 1 1 . .
    H H2 0.2653 0.1114 0.3448 0.055 Uiso calc R 1 1 . .
    C C3 0.2482(3) 0.03931(16) 0.48054(16) 0.0411(6) Uani d . 1 1 . .
    C C4 0.2704(3) -0.06207(16) 0.52460(16) 0.0396(6) Uani d . 1 1 . .
    C C5 0.2610(3) -0.12783(17) 0.61396(17) 0.0446(6) Uani d . 1 1 . .
    C C7 0.3092(3) -0.24738(18) 0.55056(18) 0.0528(7) Uani d . 1 1 . .
    H H7 0.3204 -0.3120 0.5614 0.063 Uiso calc R 1 1 . .
    C C9 0.3067(3) -0.10308(17) 0.45445(16) 0.0400(6) Uani d . 1 1 . .
    C C10 0.3198(3) -0.04409(17) 0.28547(16) 0.0440(6) Uani d . 1 1 . .
    C C11 0.4300(3) -0.11218(19) 0.25792(18) 0.0569(8) Uani d . 1 1 . .
    H H11 0.4996 -0.1513 0.2955 0.068 Uiso calc R 1 1 . .
    C C12 0.4371(4) -0.12247(19) 0.17456(19) 0.0641(8) Uani d . 1 1 . .
    H H12 0.5110 -0.1694 0.1572 0.077 Uiso calc R 1 1 . .
    C C13 0.3380(4) -0.0653(2) 0.11640(18) 0.0593(8) Uani d . 1 1 . .
    C C14 0.2295(4) 0.0028(2) 0.14461(19) 0.0673(9) Uani d . 1 1 . .
    H H14 0.1615 0.0426 0.1063 0.081 Uiso calc R 1 1 . .
    C C15 0.2187(3) 0.0137(2) 0.22876(17) 0.0576(8) Uani d . 1 1 . .
    H H15 0.1434 0.0598 0.2467 0.069 Uiso calc R 1 1 . .
    C C16 0.3471(5) -0.0769(2) 0.02497(19) 0.0868(11) Uani d . 1 1 . .
    H H161 0.4047 -0.1378 0.0243 0.130 Uiso calc R 1 1 . .
    H H162 0.3986 -0.0287 -0.0223 0.130 Uiso calc R 1 1 . .
    H H163 0.2437 -0.0716 0.0149 0.130 Uiso calc R 1 1 . .
    C C17 0.2019(3) 0.11753(16) 0.52038(15) 0.0385(6) Uani d . 1 1 . .
    C C18 0.3034(3) 0.17926(17) 0.50595(17) 0.0469(6) Uani d . 1 1 . .
    H H18 0.4013 0.1724 0.4697 0.056 Uiso calc R 1 1 . .
    C C19 0.2609(4) 0.25081(18) 0.54483(18) 0.0547(7) Uani d . 1 1 . .
    H H19 0.3304 0.2911 0.5357 0.066 Uiso calc R 1 1 . .
    C C20 0.1156(4) 0.26198(18) 0.59692(17) 0.0526(7) Uani d . 1 1 . .
    C C21 0.0117(3) 0.20315(19) 0.61140(18) 0.0542(7) Uani d . 1 1 . .
    H H21 -0.0868 0.2114 0.6466 0.065 Uiso calc R 1 1 . .
    C C22 0.0553(3) 0.13137(17) 0.57289(17) 0.0464(6) Uani d . 1 1 . .
    H H22 -0.0151 0.0915 0.5824 0.056 Uiso calc R 1 1 . .
    C C25 0.2933(3) -0.02809(17) 0.70083(16) 0.0502(7) Uani d . 1 1 . .
    H H251 0.2101 0.0249 0.7018 0.060 Uiso calc R 1 1 . .
    H H252 0.3776 -0.0073 0.6510 0.060 Uiso calc R 1 1 . .
    C C26 0.3500(3) -0.06977(19) 0.79062(17) 0.0575(8) Uani d . 1 1 . .
    H H261 0.3441 -0.0215 0.8179 0.069 Uiso calc R 1 1 . .
    H H262 0.4565 -0.1025 0.7832 0.069 Uiso calc R 1 1 . .
    C C27 0.2377(4) -0.1378(2) 0.84733(17) 0.0616(8) Uani d . 1 1 . .
    H H271 0.2794 -0.1843 0.8990 0.074 Uiso calc R 1 1 . .
    H H272 0.1375 -0.1048 0.8690 0.074 Uiso calc R 1 1 . .
    C C28 0.2244(4) -0.1824(2) 0.78017(17) 0.0687(9) Uani d . 1 1 . .
    H H281 0.3079 -0.2351 0.7782 0.082 Uiso calc R 1 1 . .
    H H282 0.1251 -0.2046 0.7959 0.082 Uiso calc R 1 1 . .
    C C30 -0.2721(3) 0.44162(18) 1.08795(17) 0.0534(7) Uani d . 1 1 . .
    H H30 -0.2631 0.3836 1.1335 0.064 Uiso calc R 1 1 . .
    C C31 -0.2150(3) 0.45403(17) 0.99830(17) 0.0468(7) Uani d . 1 1 . .
    C C32 -0.2535(3) 0.55481(16) 0.95198(16) 0.0430(6) Uani d . 1 1 . .
    C C33 -0.2305(3) 0.62018(17) 0.86288(17) 0.0458(6) Uani d . 1 1 . .
    C C35 -0.3802(3) 0.73629(19) 0.92152(19) 0.0600(8) Uani d . 1 1 . .
    H H35 -0.4276 0.7991 0.9088 0.072 Uiso calc R 1 1 . .
    C C37 -0.3365(3) 0.59490(17) 1.02000(16) 0.0446(6) Uani d . 1 1 . .
    C C38 -0.4294(3) 0.53417(18) 1.18981(16) 0.0468(7) Uani d . 1 1 . .
    C C39 -0.4229(4) 0.60878(19) 1.21646(18) 0.0626(8) Uani d . 1 1 . .
    H H39 -0.3627 0.6546 1.1787 0.075 Uiso calc R 1 1 . .
    C C40 -0.5069(4) 0.6149(2) 1.3000(2) 0.0719(9) Uani d . 1 1 . .
    H H40 -0.5041 0.6664 1.3170 0.086 Uiso calc R 1 1 . .
    C C41 -0.5943(4) 0.5476(2) 1.35894(19) 0.0617(8) Uani d . 1 1 . .
    C C42 -0.5965(3) 0.4730(2) 1.33070(19) 0.0637(8) Uani d . 1 1 . .
    H H42 -0.6538 0.4260 1.3693 0.076 Uiso calc R 1 1 . .
    C C43 -0.5163(3) 0.4657(2) 1.24665(17) 0.0552(7) Uani d . 1 1 . .
    H H43 -0.5211 0.4151 1.2289 0.066 Uiso calc R 1 1 . .
    C C44 -0.6872(4) 0.5557(3) 1.4501(2) 0.0919(11) Uani d . 1 1 . .
    H H441 -0.7890 0.5402 1.4592 0.138 Uiso calc R 1 1 . .
    H H442 -0.6971 0.6191 1.4506 0.138 Uiso calc R 1 1 . .
    H H443 -0.6342 0.5130 1.4981 0.138 Uiso calc R 1 1 . .
    C C45 -0.1389(3) 0.37392(16) 0.96308(16) 0.0426(6) Uani d . 1 1 . .
    C C46 -0.0005(3) 0.32038(18) 0.98691(17) 0.0496(7) Uani d . 1 1 . .
    H H46 0.0462 0.3350 1.0251 0.060 Uiso calc R 1 1 . .
    C C47 0.0700(3) 0.24517(19) 0.95481(19) 0.0592(8) Uani d . 1 1 . .
    H H47 0.1640 0.2099 0.9708 0.071 Uiso calc R 1 1 . .
    C C48 0.0001(4) 0.22310(19) 0.89926(19) 0.0562(7) Uani d . 1 1 . .
    C C49 -0.1395(4) 0.27394(19) 0.87578(18) 0.0563(7) Uani d . 1 1 . .
    H H49 -0.1871 0.2581 0.8388 0.068 Uiso calc R 1 1 . .
    C C50 -0.2080(3) 0.34898(18) 0.90797(17) 0.0508(7) Uani d . 1 1 . .
    H H50 -0.3026 0.3836 0.8924 0.061 Uiso calc R 1 1 . .
    C C53 -0.0106(3) 0.52431(18) 0.78628(17) 0.0521(7) Uani d . 1 1 . .
    H H531 -0.0438 0.4688 0.7858 0.062 Uiso calc R 1 1 . .
    H H532 0.0390 0.5077 0.8386 0.062 Uiso calc R 1 1 . .
    C C54 0.0984(3) 0.56544(19) 0.69815(17) 0.0571(7) Uani d . 1 1 . .
    H H541 0.1655 0.6014 0.7071 0.069 Uiso calc R 1 1 . .
    H H542 0.1625 0.5163 0.6742 0.069 Uiso calc R 1 1 . .
    C C55 -0.0132(3) 0.62861(19) 0.63545(17) 0.0574(7) Uani d . 1 1 . .
    H H551 -0.0603 0.5922 0.6133 0.069 Uiso calc R 1 1 . .
    H H552 0.0386 0.6746 0.5840 0.069 Uiso calc R 1 1 . .
    C C56 -0.1328(3) 0.67548(19) 0.69846(16) 0.0576(8) Uani d . 1 1 . .
    H H561 -0.0987 0.7299 0.7008 0.069 Uiso calc R 1 1 . .
    H H562 -0.2330 0.6952 0.6789 0.069 Uiso calc R 1 1 . .
    Cl Cl23 0.06434(12) 0.35242(6) 0.64549(6) 0.0915(3) Uani d . 1 1 . .
    Cl Cl51 0.08881(13) 0.12936(6) 0.85807(7) 0.1017(4) Uani d . 1 1 . .
    N N1 0.3089(2) -0.03272(14) 0.37193(13) 0.0444(5) Uani d . 1 1 . .
    N N6 0.2761(3) -0.22063(15) 0.62491(14) 0.0556(6) Uani d . 1 1 . .
    N N8 0.3286(2) -0.19553(14) 0.46364(14) 0.0461(5) Uani d . 1 1 . .
    N N24 0.2366(3) -0.10608(14) 0.69211(13) 0.0507(6) Uani d . 1 1 . .
    N N29 -0.3456(2) 0.52587(14) 1.10356(13) 0.0497(6) Uani d . 1 1 . .
    N N34 -0.3012(3) 0.71100(15) 0.84872(15) 0.0586(6) Uani d . 1 1 . .
    N N36 -0.4013(3) 0.68604(15) 1.00855(14) 0.0519(6) Uani d . 1 1 . .
    N N52 -0.1417(3) 0.60092(14) 0.78740(13) 0.0492(6) Uani d . 1 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
    C2 C3 . 1.363(3) ?
    C2 N1 . 1.387(3) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.452(3) ?
    C3 C17 . 1.483(3) ?
    C4 C9 . 1.407(3) ?
    C4 C5 . 1.421(3) ?
    C5 N6 . 1.352(3) ?
    C5 N24 . 1.357(3) ?
    C7 N8 . 1.323(3) ?
    C7 N6 . 1.334(3) ?
    C7 H7 . 0.9300 ?
    C9 N8 . 1.347(3) ?
    C9 N1 . 1.375(3) ?
    C10 C15 . 1.375(4) ?
    C10 C11 . 1.376(3) ?
    C10 N1 . 1.429(3) ?
    C11 C12 . 1.379(4) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.374(4) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.374(4) ?
    C13 C16 . 1.512(4) ?
    C14 C15 . 1.389(4) ?
    C14 H14 . 0.9300 ?
    C15 H15 . 0.9300 ?
    C16 H161 . 0.9600 ?
    C16 H162 . 0.9600 ?
    C16 H163 . 0.9600 ?
    C17 C22 . 1.387(3) ?
    C17 C18 . 1.388(3) ?
    C18 C19 . 1.382(3) ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.370(4) ?
    C19 H19 . 0.9300 ?
    C20 C21 . 1.370(4) ?
    C20 Cl23 . 1.742(3) ?
    C21 C22 . 1.381(3) ?
    C21 H21 . 0.9300 ?
    C22 H22 . 0.9300 ?
    C25 N24 . 1.467(3) ?
    C25 C26 . 1.510(3) ?
    C25 H251 . 0.9700 ?
    C25 H252 . 0.9700 ?
    C26 C27 . 1.514(4) ?
    C26 H261 . 0.9700 ?
    C26 H262 . 0.9700 ?
    C27 C28 . 1.503(4) ?
    C27 H271 . 0.9700 ?
    C27 H272 . 0.9700 ?
    C28 N24 . 1.475(3) ?
    C28 H281 . 0.9700 ?
    C28 H282 . 0.9700 ?
    C30 C31 . 1.355(3) ?
    C30 N29 . 1.387(3) ?
    C30 H30 . 0.9300 ?
    C31 C32 . 1.459(3) ?
    C31 C45 . 1.485(3) ?
    C32 C37 . 1.404(3) ?
    C32 C33 . 1.418(3) ?
    C33 N34 . 1.355(3) ?
    C33 N52 . 1.357(3) ?
    C35 N36 . 1.318(3) ?
    C35 N34 . 1.337(3) ?
    C35 H35 . 0.9300 ?
    C37 N36 . 1.351(3) ?
    C37 N29 . 1.376(3) ?
    C38 C39 . 1.374(4) ?
    C38 C43 . 1.375(4) ?
    C38 N29 . 1.430(3) ?
    C39 C40 . 1.383(4) ?
    C39 H39 . 0.9300 ?
    C40 C41 . 1.375(4) ?
    C40 H40 . 0.9300 ?
    C41 C42 . 1.378(4) ?
    C41 C44 . 1.519(4) ?
    C42 C43 . 1.386(4) ?
    C42 H42 . 0.9300 ?
    C43 H43 . 0.9300 ?
    C44 H441 . 0.9600 ?
    C44 H442 . 0.9600 ?
    C44 H443 . 0.9600 ?
    C45 C46 . 1.377(3) ?
    C45 C50 . 1.387(3) ?
    C46 C47 . 1.385(4) ?
    C46 H46 . 0.9300 ?
    C47 C48 . 1.372(4) ?
    C47 H47 . 0.9300 ?
    C48 C49 . 1.374(4) ?
    C48 Cl51 . 1.737(3) ?
    C49 C50 . 1.380(4) ?
    C49 H49 . 0.9300 ?
    C50 H50 . 0.9300 ?
    C53 N52 . 1.458(3) ?
    C53 C54 . 1.520(3) ?
    C53 H531 . 0.9700 ?
    C53 H532 . 0.9700 ?
    C54 C55 . 1.516(4) ?
    C54 H541 . 0.9700 ?
    C54 H542 . 0.9700 ?
    C55 C56 . 1.517(4) ?
    C55 H551 . 0.9700 ?
    C55 H552 . 0.9700 ?
    C56 N52 . 1.472(3) ?
    C56 H561 . 0.9700 ?
    C56 H562 . 0.9700 ?
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
    C3 C2 N1 . . 111.1(2) ?
    C3 C2 H2 . . 124.5 ?
    N1 C2 H2 . . 124.5 ?
    C2 C3 C4 . . 106.1(2) ?
    C2 C3 C17 . . 123.5(2) ?
    C4 C3 C17 . . 130.3(2) ?
    C9 C4 C5 . . 114.5(2) ?
    C9 C4 C3 . . 106.3(2) ?
    C5 C4 C3 . . 139.1(2) ?
    N6 C5 N24 . . 115.3(2) ?
    N6 C5 C4 . . 119.1(2) ?
    N24 C5 C4 . . 125.6(2) ?
    N8 C7 N6 . . 129.5(2) ?
    N8 C7 H7 . . 115.3 ?
    N6 C7 H7 . . 115.3 ?
    N8 C9 N1 . . 123.6(2) ?
    N8 C9 C4 . . 127.2(2) ?
    N1 C9 C4 . . 109.1(2) ?
    C15 C10 C11 . . 119.3(2) ?
    C15 C10 N1 . . 119.6(2) ?
    C11 C10 N1 . . 121.0(2) ?
    C10 C11 C12 . . 120.0(3) ?
    C10 C11 H11 . . 120.0 ?
    C12 C11 H11 . . 120.0 ?
    C13 C12 C11 . . 121.9(3) ?
    C13 C12 H12 . . 119.1 ?
    C11 C12 H12 . . 119.1 ?
    C14 C13 C12 . . 117.4(3) ?
    C14 C13 C16 . . 121.1(3) ?
    C12 C13 C16 . . 121.5(3) ?
    C13 C14 C15 . . 121.8(3) ?
    C13 C14 H14 . . 119.1 ?
    C15 C14 H14 . . 119.1 ?
    C10 C15 C14 . . 119.6(3) ?
    C10 C15 H15 . . 120.2 ?
    C14 C15 H15 . . 120.2 ?
    C13 C16 H161 . . 109.5 ?
    C13 C16 H162 . . 109.5 ?
    H161 C16 H162 . . 109.5 ?
    C13 C16 H163 . . 109.5 ?
    H161 C16 H163 . . 109.5 ?
    H162 C16 H163 . . 109.5 ?
    C22 C17 C18 . . 118.0(2) ?
    C22 C17 C3 . . 120.9(2) ?
    C18 C17 C3 . . 121.0(2) ?
    C19 C18 C17 . . 120.8(2) ?
    C19 C18 H18 . . 119.6 ?
    C17 C18 H18 . . 119.6 ?
    C20 C19 C18 . . 119.6(3) ?
    C20 C19 H19 . . 120.2 ?
    C18 C19 H19 . . 120.2 ?
    C21 C20 C19 . . 121.1(3) ?
    C21 C20 Cl23 . . 120.0(2) ?
    C19 C20 Cl23 . . 118.9(2) ?
    C20 C21 C22 . . 119.1(3) ?
    C20 C21 H21 . . 120.5 ?
    C22 C21 H21 . . 120.5 ?
    C21 C22 C17 . . 121.4(3) ?
    C21 C22 H22 . . 119.3 ?
    C17 C22 H22 . . 119.3 ?
    N24 C25 C26 . . 103.9(2) ?
    N24 C25 H251 . . 111.0 ?
    C26 C25 H251 . . 111.0 ?
    N24 C25 H252 . . 111.0 ?
    C26 C25 H252 . . 111.0 ?
    H251 C25 H252 . . 109.0 ?
    C25 C26 C27 . . 102.6(2) ?
    C25 C26 H261 . . 111.2 ?
    C27 C26 H261 . . 111.2 ?
    C25 C26 H262 . . 111.2 ?
    C27 C26 H262 . . 111.2 ?
    H261 C26 H262 . . 109.2 ?
    C28 C27 C26 . . 102.1(2) ?
    C28 C27 H271 . . 111.4 ?
    C26 C27 H271 . . 111.4 ?
    C28 C27 H272 . . 111.4 ?
    C26 C27 H272 . . 111.4 ?
    H271 C27 H272 . . 109.2 ?
    N24 C28 C27 . . 104.3(2) ?
    N24 C28 H281 . . 110.9 ?
    C27 C28 H281 . . 110.9 ?
    N24 C28 H282 . . 110.9 ?
    C27 C28 H282 . . 110.9 ?
    H281 C28 H282 . . 108.9 ?
    C31 C30 N29 . . 111.8(2) ?
    C31 C30 H30 . . 124.1 ?
    N29 C30 H30 . . 124.1 ?
    C30 C31 C32 . . 105.8(2) ?
    C30 C31 C45 . . 122.3(2) ?
    C32 C31 C45 . . 131.8(2) ?
    C37 C32 C33 . . 114.6(2) ?
    C37 C32 C31 . . 106.1(2) ?
    C33 C32 C31 . . 139.3(2) ?
    N34 C33 N52 . . 114.8(2) ?
    N34 C33 C32 . . 119.2(2) ?
    N52 C33 C32 . . 126.0(2) ?
    N36 C35 N34 . . 130.0(2) ?
    N36 C35 H35 . . 115.0 ?
    N34 C35 H35 . . 115.0 ?
    N36 C37 N29 . . 123.3(2) ?
    N36 C37 C32 . . 127.2(2) ?
    N29 C37 C32 . . 109.4(2) ?
    C39 C38 C43 . . 120.1(2) ?
    C39 C38 N29 . . 120.9(2) ?
    C43 C38 N29 . . 119.0(2) ?
    C38 C39 C40 . . 119.2(3) ?
    C38 C39 H39 . . 120.4 ?
    C40 C39 H39 . . 120.4 ?
    C41 C40 C39 . . 122.4(3) ?
    C41 C40 H40 . . 118.8 ?
    C39 C40 H40 . . 118.8 ?
    C40 C41 C42 . . 116.9(3) ?
    C40 C41 C44 . . 121.8(3) ?
    C42 C41 C44 . . 121.3(3) ?
    C41 C42 C43 . . 122.2(3) ?
    C41 C42 H42 . . 118.9 ?
    C43 C42 H42 . . 118.9 ?
    C38 C43 C42 . . 119.2(3) ?
    C38 C43 H43 . . 120.4 ?
    C42 C43 H43 . . 120.4 ?
    C41 C44 H441 . . 109.5 ?
    C41 C44 H442 . . 109.5 ?
    H441 C44 H442 . . 109.5 ?
    C41 C44 H443 . . 109.5 ?
    H441 C44 H443 . . 109.5 ?
    H442 C44 H443 . . 109.5 ?
    C46 C45 C50 . . 118.2(2) ?
    C46 C45 C31 . . 120.8(2) ?
    C50 C45 C31 . . 120.9(2) ?
    C45 C46 C47 . . 121.0(3) ?
    C45 C46 H46 . . 119.5 ?
    C47 C46 H46 . . 119.5 ?
    C48 C47 C46 . . 119.5(3) ?
    C48 C47 H47 . . 120.3 ?
    C46 C47 H47 . . 120.3 ?
    C47 C48 C49 . . 121.0(3) ?
    C47 C48 Cl51 . . 119.7(2) ?
    C49 C48 Cl51 . . 119.3(2) ?
    C48 C49 C50 . . 118.9(3) ?
    C48 C49 H49 . . 120.6 ?
    C50 C49 H49 . . 120.6 ?
    C49 C50 C45 . . 121.5(3) ?
    C49 C50 H50 . . 119.3 ?
    C45 C50 H50 . . 119.3 ?
    N52 C53 C54 . . 103.2(2) ?
    N52 C53 H531 . . 111.1 ?
    C54 C53 H531 . . 111.1 ?
    N52 C53 H532 . . 111.1 ?
    C54 C53 H532 . . 111.1 ?
    H531 C53 H532 . . 109.1 ?
    C55 C54 C53 . . 102.9(2) ?
    C55 C54 H541 . . 111.2 ?
    C53 C54 H541 . . 111.2 ?
    C55 C54 H542 . . 111.2 ?
    C53 C54 H542 . . 111.2 ?
    H541 C54 H542 . . 109.1 ?
    C54 C55 C56 . . 101.6(2) ?
    C54 C55 H551 . . 111.5 ?
    C56 C55 H551 . . 111.5 ?
    C54 C55 H552 . . 111.5 ?
    C56 C55 H552 . . 111.5 ?
    H551 C55 H552 . . 109.3 ?
    N52 C56 C55 . . 103.4(2) ?
    N52 C56 H561 . . 111.1 ?
    C55 C56 H561 . . 111.1 ?
    N52 C56 H562 . . 111.1 ?
    C55 C56 H562 . . 111.1 ?
    H561 C56 H562 . . 109.0 ?
    C9 N1 C2 . . 107.42(19) ?
    C9 N1 C10 . . 126.5(2) ?
    C2 N1 C10 . . 125.3(2) ?
    C7 N6 C5 . . 118.3(2) ?
    C7 N8 C9 . . 111.1(2) ?
    C5 N24 C25 . . 124.8(2) ?
    C5 N24 C28 . . 119.1(2) ?
    C25 N24 C28 . . 109.5(2) ?
    C37 N29 C30 . . 106.9(2) ?
    C37 N29 C38 . . 128.0(2) ?
    C30 N29 C38 . . 124.7(2) ?
    C35 N34 C33 . . 117.7(2) ?
    C35 N36 C37 . . 110.8(2) ?
    C33 N52 C53 . . 125.8(2) ?
    C33 N52 C56 . . 119.9(2) ?
    C53 N52 C56 . . 110.9(2) ?
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
    N1 C2 C3 C4 . . . . -0.2(3) ?
    N1 C2 C3 C17 . . . . -177.8(2) ?
    C2 C3 C4 C9 . . . . -0.2(3) ?
    C17 C3 C4 C9 . . . . 177.2(2) ?
    C2 C3 C4 C5 . . . . -177.6(3) ?
    C17 C3 C4 C5 . . . . -0.2(5) ?
    C9 C4 C5 N6 . . . . -4.5(3) ?
    C3 C4 C5 N6 . . . . 172.7(3) ?
    C9 C4 C5 N24 . . . . 176.0(2) ?
    C3 C4 C5 N24 . . . . -6.8(5) ?
    C5 C4 C9 N8 . . . . 1.9(4) ?
    C3 C4 C9 N8 . . . . -176.2(2) ?
    C5 C4 C9 N1 . . . . 178.7(2) ?
    C3 C4 C9 N1 . . . . 0.6(3) ?
    C15 C10 C11 C12 . . . . -0.6(4) ?
    N1 C10 C11 C12 . . . . 179.3(2) ?
    C10 C11 C12 C13 . . . . 1.0(4) ?
    C11 C12 C13 C14 . . . . -0.5(4) ?
    C11 C12 C13 C16 . . . . 179.8(3) ?
    C12 C13 C14 C15 . . . . -0.4(4) ?
    C16 C13 C14 C15 . . . . 179.3(3) ?
    C11 C10 C15 C14 . . . . -0.3(4) ?
    N1 C10 C15 C14 . . . . 179.8(2) ?
    C13 C14 C15 C10 . . . . 0.8(5) ?
    C2 C3 C17 C22 . . . . 112.0(3) ?
    C4 C3 C17 C22 . . . . -65.1(4) ?
    C2 C3 C17 C18 . . . . -67.7(3) ?
    C4 C3 C17 C18 . . . . 115.2(3) ?
    C22 C17 C18 C19 . . . . 1.7(4) ?
    C3 C17 C18 C19 . . . . -178.6(2) ?
    C17 C18 C19 C20 . . . . -1.2(4) ?
    C18 C19 C20 C21 . . . . 0.2(4) ?
    C18 C19 C20 Cl23 . . . . 179.88(19) ?
    C19 C20 C21 C22 . . . . 0.3(4) ?
    Cl23 C20 C21 C22 . . . . -179.42(19) ?
    C20 C21 C22 C17 . . . . 0.3(4) ?
    C18 C17 C22 C21 . . . . -1.2(4) ?
    C3 C17 C22 C21 . . . . 179.1(2) ?
    N24 C25 C26 C27 . . . . -33.8(3) ?
    C25 C26 C27 C28 . . . . 42.1(3) ?
    C26 C27 C28 N24 . . . . -34.2(3) ?
    N29 C30 C31 C32 . . . . 0.5(3) ?
    N29 C30 C31 C45 . . . . -176.5(2) ?
    C30 C31 C32 C37 . . . . -1.4(3) ?
    C45 C31 C32 C37 . . . . 175.1(3) ?
    C30 C31 C32 C33 . . . . 177.5(3) ?
    C45 C31 C32 C33 . . . . -5.9(5) ?
    C37 C32 C33 N34 . . . . -6.7(4) ?
    C31 C32 C33 N34 . . . . 174.3(3) ?
    C37 C32 C33 N52 . . . . 173.1(2) ?
    C31 C32 C33 N52 . . . . -5.8(5) ?
    C33 C32 C37 N36 . . . . 3.6(4) ?
    C31 C32 C37 N36 . . . . -177.2(2) ?
    C33 C32 C37 N29 . . . . -177.4(2) ?
    C31 C32 C37 N29 . . . . 1.9(3) ?
    C43 C38 C39 C40 . . . . -1.2(4) ?
    N29 C38 C39 C40 . . . . 179.4(3) ?
    C38 C39 C40 C41 . . . . 1.6(5) ?
    C39 C40 C41 C42 . . . . -0.7(5) ?
    C39 C40 C41 C44 . . . . -179.4(3) ?
    C40 C41 C42 C43 . . . . -0.6(5) ?
    C44 C41 C42 C43 . . . . 178.1(3) ?
    C39 C38 C43 C42 . . . . 0.0(4) ?
    N29 C38 C43 C42 . . . . 179.4(2) ?
    C41 C42 C43 C38 . . . . 1.0(4) ?
    C30 C31 C45 C46 . . . . -65.2(4) ?
    C32 C31 C45 C46 . . . . 118.8(3) ?
    C30 C31 C45 C50 . . . . 112.5(3) ?
    C32 C31 C45 C50 . . . . -63.5(4) ?
    C50 C45 C46 C47 . . . . 1.7(4) ?
    C31 C45 C46 C47 . . . . 179.5(2) ?
    C45 C46 C47 C48 . . . . -0.7(4) ?
    C46 C47 C48 C49 . . . . -0.6(4) ?
    C46 C47 C48 Cl51 . . . . 179.5(2) ?
    C47 C48 C49 C50 . . . . 1.0(4) ?
    Cl51 C48 C49 C50 . . . . -179.2(2) ?
    C48 C49 C50 C45 . . . . 0.1(4) ?
    C46 C45 C50 C49 . . . . -1.4(4) ?
    C31 C45 C50 C49 . . . . -179.1(2) ?
    N52 C53 C54 C55 . . . . -33.6(3) ?
    C53 C54 C55 C56 . . . . 42.5(3) ?
    C54 C55 C56 N52 . . . . -34.9(3) ?
    N8 C9 N1 C2 . . . . 176.2(2) ?
    C4 C9 N1 C2 . . . . -0.7(3) ?
    N8 C9 N1 C10 . . . . 6.1(4) ?
    C4 C9 N1 C10 . . . . -170.8(2) ?
    C3 C2 N1 C9 . . . . 0.6(3) ?
    C3 C2 N1 C10 . . . . 170.8(2) ?
    C15 C10 N1 C9 . . . . 131.9(3) ?
    C11 C10 N1 C9 . . . . -48.0(4) ?
    C15 C10 N1 C2 . . . . -36.5(4) ?
    C11 C10 N1 C2 . . . . 143.6(3) ?
    N8 C7 N6 C5 . . . . -1.2(4) ?
    N24 C5 N6 C7 . . . . -176.2(2) ?
    C4 C5 N6 C7 . . . . 4.3(4) ?
    N6 C7 N8 C9 . . . . -1.5(4) ?
    N1 C9 N8 C7 . . . . -175.4(2) ?
    C4 C9 N8 C7 . . . . 0.9(4) ?
    N6 C5 N24 C25 . . . . 146.9(2) ?
    C4 C5 N24 C25 . . . . -33.6(4) ?
    N6 C5 N24 C28 . . . . -1.6(4) ?
    C4 C5 N24 C28 . . . . 177.9(3) ?
    C26 C25 N24 C5 . . . . -138.3(3) ?
    C26 C25 N24 C28 . . . . 12.8(3) ?
    C27 C28 N24 C5 . . . . 166.5(2) ?
    C27 C28 N24 C25 . . . . 13.6(3) ?
    N36 C37 N29 C30 . . . . 177.5(2) ?
    C32 C37 N29 C30 . . . . -1.7(3) ?
    N36 C37 N29 C38 . . . . 4.5(4) ?
    C32 C37 N29 C38 . . . . -174.7(2) ?
    C31 C30 N29 C37 . . . . 0.7(3) ?
    C31 C30 N29 C38 . . . . 174.0(2) ?
    C39 C38 N29 C37 . . . . -45.6(4) ?
    C43 C38 N29 C37 . . . . 135.0(3) ?
    C39 C38 N29 C30 . . . . 142.5(3) ?
    C43 C38 N29 C30 . . . . -36.9(4) ?
    N36 C35 N34 C33 . . . . 0.5(5) ?
    N52 C33 N34 C35 . . . . -174.7(3) ?
    C32 C33 N34 C35 . . . . 5.1(4) ?
    N34 C35 N36 C37 . . . . -3.7(4) ?
    N29 C37 N36 C35 . . . . -177.6(3) ?
    C32 C37 N36 C35 . . . . 1.3(4) ?
    N34 C33 N52 C53 . . . . 155.2(2) ?
    C32 C33 N52 C53 . . . . -24.7(4) ?
    N34 C33 N52 C56 . . . . -2.2(4) ?
    C32 C33 N52 C56 . . . . 177.9(3) ?
    C54 C53 N52 C33 . . . . -147.2(3) ?
    C54 C53 N52 C56 . . . . 11.9(3) ?
    C55 C56 N52 C33 . . . . 175.1(2) ?
    C55 C56 N52 C53 . . . . 14.6(3) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    C18 H18 Cg1 2_656 0.93 2.68 3.483(3) 144 yes
    C46 H46 Cg2 2_567 0.93 2.73 3.549(3) 147 yes
    C25 H251 Cg3 1_555 0.97 2.79 3.462(3) 127 yes
    C53 H531 Cg4 1_555 0.97 2.84 3.506(3) 127 yes
