##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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 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. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     SHELXL
_journal_date_recd_electronic     2007-12-21
_journal_date_accepted     2008-01-07
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      2
_journal_page_first     o503
_journal_page_last     o503
_journal_paper_category     QO
_journal_coeditor_code     GG3141
_publ_contact_author_name     'Gainsford, Graeme J.'
_publ_contact_author_address
;Industrial Research Limited
 PO Box 31-310
 Lower Hutt
 New Zealand
;
_publ_contact_author_email     g.gainsford@irl.cri.nz
_publ_contact_author_fax     '64(4)931 3142'
_publ_contact_author_phone     '64(4)931 3518'
_publ_section_title
;\
2-{3-Cyano-5,5-dimethyl-4-[4-(piperidin-1-yl)buta-1,3-dienyl]-2,5-dihydrofuran-\
2-ylidene}malononitrile
;
loop_
    _publ_author_name
    _publ_author_address
    'Gainsford, Graeme J.'
;Industrial Research Limited
 PO Box 31-310
 Lower Hutt
 New Zealand
;
    'Bhuiyan, M. Delower H.'
;Industrial Research Limited
 PO Box 31-310
 Lower Hutt
 New Zealand
;
    'Kay, Andrew J.'
;Industrial Research Limited
 PO Box 31-310
 Lower Hutt
 New Zealand
;
    'Spek, Anthony L.'
;Utrecht University,
 Padualaan 8,
 3584 CH Utrecht,
 The Netherlands
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-{3-Cyano-5,5-dimethyl-4-[4-(piperidin-1-yl)buta-1,3-dienyl]-
2,5-dihydrofuran-2-ylidene}malononitrile
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H20 N4 O'
_chemical_formula_sum     'C19 H20 N4 O'
_chemical_formula_iupac     'C19 H20 N4 O'
_chemical_formula_weight     320.39
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     15.094(4)
_cell_length_b     18.994(5)
_cell_length_c     13.332(4)
_cell_angle_alpha     90.00
_cell_angle_beta     116.193(8)
_cell_angle_gamma     90.00
_cell_volume     3429.7(16)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     4176
_cell_measurement_theta_min     2.7
_cell_measurement_theta_max     30.2
_cell_measurement_temperature     119(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     red
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.09
_exptl_crystal_density_diffrn     1.241
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1360
_exptl_absorpt_coefficient_mu     0.080
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details
;
(Blessing, 1995)
;
_exptl_absorpt_correction_T_min     0.733
_exptl_absorpt_correction_T_max     1.0
_exptl_special_details
;
;
_diffrn_ambient_temperature     119(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
;
Bruker--Nonius APEXII CCD area-detector diffractometer
;
_diffrn_measurement_method     '/f and /w scans'
_diffrn_detector_area_resol_mean     8.192
_diffrn_reflns_number     18712
_diffrn_reflns_av_R_equivalents     0.088
_diffrn_reflns_av_sigmaI/netI     0.1504
_diffrn_reflns_theta_min     2.01
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.919
_diffrn_measured_fraction_theta_full     0.919
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -22
_diffrn_reflns_limit_k_max     22
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
 An extinction parameter was refined.
 Data above 2θ 50° were excluded on the basis of low
 intensity/error ratio. A total of 477 reflections
 were either not recorded or affected by the backstop
 within this θ limit (of 6035 expected). A further 13 reflections
 (and their Friedel opposites) were omitted from the refinement
 on the basis of being clearly outliers (with Fₒ<<Fc).
 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 > 2sigma(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     11128
_reflns_number_gt     5766
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1698
_refine_ls_R_factor_gt     0.0786
_refine_ls_wR_factor_gt     0.1661
_refine_ls_wR_factor_ref     0.2027
_refine_ls_goodness_of_fit_ref     1.024
_refine_ls_restrained_S_all     1.024
_refine_ls_number_reflns     11128
_refine_ls_number_parameters     424
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                'w=1/[σ²(Fo²)+(0.041P)²+5.943P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.457
_refine_diff_density_min     -0.361
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.0014(2)
_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' 0.0033 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'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2005)'
_computing_cell_refinement     'SAINT (Bruker, 2005)'
_computing_data_reduction
;
SAINT (Bruker, 2005) and SADABS (Sheldrick, 2003)
;
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2003)
;
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_disorder_assembly
    _atom_site_disorder_group
    O O1 0.7393(3) 0.8303(2) 0.4515(3) 0.0343(10) Uani d . 1 . .
    N N1 0.9567(4) 0.7590(3) 0.2970(5) 0.0422(15) Uani d . 1 . .
    N N2 0.8344(4) 0.9570(3) 0.3440(4) 0.0489(15) Uani d . 1 . .
    N N3 0.8724(4) 0.6091(3) 0.4162(5) 0.0473(15) Uani d . 1 . .
    N N4 0.5250(3) 0.5399(2) 0.7252(4) 0.0326(12) Uani d . 1 . .
    C C1 0.9063(4) 0.7849(3) 0.3282(5) 0.0356(16) Uani d . 1 . .
    C C2 0.8470(4) 0.8229(3) 0.3707(5) 0.0321(14) Uani d . 1 . .
    C C3 0.8397(4) 0.8966(4) 0.3552(5) 0.0362(15) Uani d . 1 . .
    C C4 0.7276(4) 0.7135(3) 0.5029(5) 0.0289(15) Uani d . 1 . .
    C C5 0.6857(4) 0.7869(3) 0.4989(5) 0.0311(15) Uani d . 1 . .
    C C6 0.7962(4) 0.7888(3) 0.4209(5) 0.0305(14) Uani d . 1 . .
    C C7 0.7908(4) 0.7191(3) 0.4492(5) 0.0283(14) Uiso d . 1 . .
    C C8 0.5770(4) 0.7903(3) 0.4147(5) 0.0395(16) Uani d . 1 . .
    H H8A 0.5545 0.8394 0.4055 0.059 Uiso calc R 1 . .
    H H8B 0.5378 0.7621 0.4420 0.059 Uiso calc R 1 . .
    H H8C 0.5690 0.7718 0.3426 0.059 Uiso calc R 1 . .
    C C9 0.7073(4) 0.8205(3) 0.6121(5) 0.0400(17) Uani d . 1 . .
    H H9A 0.6905 0.8707 0.6015 0.060 Uiso calc R 1 . .
    H H9B 0.7776 0.8151 0.6630 0.060 Uiso calc R 1 . .
    H H9C 0.6677 0.7971 0.6440 0.060 Uiso calc R 1 . .
    C C10 0.8375(4) 0.6601(3) 0.4304(5) 0.0336(15) Uani d . 1 . .
    C C11 0.7080(4) 0.6540(3) 0.5476(5) 0.0344(16) Uani d . 1 . .
    H H11 0.7436 0.6126 0.5486 0.041 Uiso calc R 1 . .
    C C12 0.6398(4) 0.6493(3) 0.5920(4) 0.0297(14) Uani d . 1 . .
    H H12 0.6046 0.6906 0.5925 0.036 Uiso calc R 1 . .
    C C13 0.6206(4) 0.5883(3) 0.6352(5) 0.0323(15) Uani d . 1 . .
    H H13 0.6557 0.5462 0.6387 0.039 Uiso calc R 1 . .
    C C14 0.5483(4) 0.5901(3) 0.6736(5) 0.0362(16) Uani d . 1 . .
    H H14 0.5117 0.6327 0.6610 0.043 Uiso calc R 1 . .
    C C15 0.4434(4) 0.5482(3) 0.7556(5) 0.0389(16) Uani d . 1 . .
    H H15A 0.4120 0.5948 0.7305 0.047 Uiso calc R 1 . .
    H H15B 0.4690 0.5458 0.8379 0.047 Uiso calc R 1 . .
    C C16 0.3684(4) 0.4911(3) 0.7020(5) 0.0438(17) Uiso d . 1 . .
    H H16A 0.3393 0.4959 0.6197 0.053 Uiso calc R 1 . .
    H H16B 0.3147 0.4958 0.7250 0.053 Uiso calc R 1 . .
    C C17 0.4162(4) 0.4197(3) 0.7361(5) 0.0448(17) Uani d . 1 . .
    H H17A 0.3667 0.3824 0.6982 0.054 Uiso calc R 1 . .
    H H17B 0.4412 0.4135 0.8178 0.054 Uiso calc R 1 . .
    C C18 0.5018(4) 0.4130(3) 0.7040(6) 0.0430(17) Uiso d . 1 . .
    H H18A 0.5355 0.3673 0.7307 0.052 Uiso calc R 1 . .
    H H18B 0.4756 0.4143 0.6216 0.052 Uiso calc R 1 . .
    C C19 0.5750(4) 0.4721(3) 0.7545(5) 0.0391(16) Uani d . 1 . .
    H H19A 0.6084 0.4669 0.8368 0.047 Uiso calc R 1 . .
    H H19B 0.6259 0.4697 0.7267 0.047 Uiso calc R 1 . .
    O O1' 0.2394(3) 0.8340(2) 0.2535(3) 0.0340(10) Uani d . 1 . .
    N N1' 0.4636(4) 0.7639(3) 0.6209(5) 0.0443(15) Uani d . 1 . .
    N N2' 0.3455(4) 0.9652(3) 0.4508(4) 0.0480(15) Uani d . 1 . .
    N N3' 0.3582(4) 0.6149(3) 0.4407(4) 0.0443(15) Uani d . 1 . .
    N N4' 0.0597(3) 0.5220(2) -0.2095(4) 0.0313(12) Uani d . 1 . .
    C C1' 0.4113(4) 0.7928(3) 0.5417(5) 0.0347(15) Uani d . 1 . .
    C C2' 0.3478(4) 0.8300(3) 0.4436(5) 0.0288(14) Uani d . 1 . .
    C C3' 0.3455(4) 0.9041(4) 0.4475(5) 0.0334(15) Uani d . 1 . .
    C C4' 0.2259(4) 0.7152(3) 0.1981(5) 0.0269(14) Uani d . 1 . .
    C C5' 0.1910(4) 0.7881(3) 0.1521(5) 0.0320(15) Uani d . 1 . .
    C C6' 0.2942(4) 0.7932(3) 0.3443(5) 0.0311(15) Uani d . 1 . .
    C C7' 0.2857(4) 0.7224(3) 0.3153(5) 0.0295(15) Uani d . 1 . .
    C C8' 0.0811(4) 0.7979(3) 0.1116(5) 0.0465(18) Uani d . 1 . .
    H H8'A 0.0653 0.8482 0.1026 0.070 Uiso calc R 1 . .
    H H8'B 0.0613 0.7778 0.1663 0.070 Uiso calc R 1 . .
    H H8'C 0.0456 0.7740 0.0396 0.070 Uiso calc R 1 . .
    C C9' 0.2278(4) 0.8151(3) 0.0713(5) 0.0422(17) Uani d . 1 . .
    H H9'A 0.2170 0.8660 0.0622 0.063 Uiso calc R 1 . .
    H H9'B 0.1918 0.7918 -0.0011 0.063 Uiso calc R 1 . .
    H H9'C 0.2984 0.8050 0.1002 0.063 Uiso calc R 1 . .
    C C10' 0.3282(4) 0.6651(3) 0.3876(5) 0.0315(15) Uani d . 1 . .
    C C11' 0.2043(4) 0.6539(3) 0.1390(5) 0.0303(14) Uani d . 1 . .
    H H11' 0.2299 0.6119 0.1804 0.036 Uiso calc R 1 . .
    C C12' 0.1479(4) 0.6464(3) 0.0229(5) 0.0296(14) Uani d . 1 . .
    H H12' 0.1188 0.6872 -0.0203 0.035 Uiso calc R 1 . .
    C C13' 0.1330(4) 0.5823(3) -0.0312(5) 0.0318(15) Uani d . 1 . .
    H H13' 0.1608 0.5407 0.0103 0.038 Uiso calc R 1 . .
    C C14' 0.0770(4) 0.5789(3) -0.1468(5) 0.0330(15) Uani d . 1 . .
    H H14' 0.0486 0.6217 -0.1841 0.040 Uiso calc R 1 . .
    C C15' -0.0091(4) 0.5216(3) -0.3290(5) 0.0425(18) Uani d . 1 . .
    H H15C 0.0259 0.5050 -0.3723 0.051 Uiso calc R 1 . .
    H H15D -0.0324 0.5702 -0.3534 0.051 Uiso calc R 1 . .
    C C16' -0.0964(4) 0.4748(3) -0.3530(5) 0.0440(17) Uani d . 1 . .
    H H16C -0.1387 0.4728 -0.4346 0.053 Uiso calc R 1 . .
    H H16D -0.1362 0.4944 -0.3172 0.053 Uiso calc R 1 . .
    C C17' -0.0618(4) 0.4010(3) -0.3085(5) 0.0444(18) Uani d . 1 . .
    H H17C -0.0300 0.3789 -0.3516 0.053 Uiso calc R 1 . .
    H H17D -0.1194 0.3718 -0.3183 0.053 Uiso calc R 1 . .
    C C18' 0.0114(4) 0.4035(3) -0.1846(5) 0.0419(18) Uani d . 1 . .
    H H18C -0.0224 0.4209 -0.1406 0.050 Uiso calc R 1 . .
    H H18D 0.0362 0.3554 -0.1583 0.050 Uiso calc R 1 . .
    C C19' 0.0967(4) 0.4509(3) -0.1666(5) 0.0374(15) Uani d . 1 . .
    H H19C 0.1422 0.4535 -0.0858 0.045 Uiso calc R 1 . .
    H H19D 0.1337 0.4317 -0.2060 0.045 Uiso calc R 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
    O1 C6 . 1.355(6) no
    O1 C5 . 1.478(6) no
    N1 C1 . 1.128(7) ?
    N2 C3 . 1.156(7) ?
    N3 C10 . 1.157(7) ?
    N4 C14 . 1.310(7) no
    N4 C19 . 1.458(6) ?
    N4 C15 . 1.466(7) ?
    C1 C2 . 1.446(8) ?
    C2 C6 . 1.381(8) ?
    C2 C3 . 1.412(8) ?
    C4 C11 . 1.370(7) no
    C4 C7 . 1.426(8) no
    C4 C5 . 1.523(8) ?
    C5 C8 . 1.527(7) ?
    C5 C9 . 1.534(8) ?
    C6 C7 . 1.390(7) ?
    C7 C10 . 1.404(8) ?
    C8 H8A . 0.9800 ?
    C8 H8B . 0.9800 ?
    C8 H8C . 0.9800 ?
    C9 H9A . 0.9800 ?
    C9 H9B . 0.9800 ?
    C9 H9C . 0.9800 ?
    C11 C12 . 1.398(7) no
    C11 H11 . 0.9500 ?
    C12 C13 . 1.380(7) no
    C12 H12 . 0.9500 ?
    C13 C14 . 1.396(8) no
    C13 H13 . 0.9500 ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.501(7) ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C16 C17 . 1.509(7) ?
    C16 H16A . 0.9900 ?
    C16 H16B . 0.9900 ?
    C17 C18 . 1.536(8) ?
    C17 H17A . 0.9900 ?
    C17 H17B . 0.9900 ?
    C18 C19 . 1.508(7) ?
    C18 H18A . 0.9900 ?
    C18 H18B . 0.9900 ?
    C19 H19A . 0.9900 ?
    C19 H19B . 0.9900 ?
    O1' C6' . 1.365(6) no
    O1' C5' . 1.500(6) no
    N1' C1' . 1.141(7) ?
    N2' C3' . 1.161(7) ?
    N3' C10' . 1.154(7) ?
    N4' C14' . 1.320(6) no
    N4' C15' . 1.468(6) ?
    N4' C19' . 1.477(6) ?
    C1' C2' . 1.422(8) ?
    C2' C6' . 1.396(7) ?
    C2' C3' . 1.410(8) ?
    C4' C11' . 1.362(7) no
    C4' C7' . 1.425(7) no
    C4' C5' . 1.511(7) ?
    C5' C9' . 1.503(8) ?
    C5' C8' . 1.512(7) ?
    C6' C7' . 1.390(7) ?
    C7' C10' . 1.407(8) ?
    C8' H8'A . 0.9800 ?
    C8' H8'B . 0.9800 ?
    C8' H8'C . 0.9800 ?
    C9' H9'A . 0.9800 ?
    C9' H9'B . 0.9800 ?
    C9' H9'C . 0.9800 ?
    C11' C12' . 1.405(8) no
    C11' H11' . 0.9500 ?
    C12' C13' . 1.382(7) no
    C12' H12' . 0.9500 ?
    C13' C14' . 1.395(7) no
    C13' H13' . 0.9500 ?
    C14' H14' . 0.9500 ?
    C15' C16' . 1.503(8) ?
    C15' H15C . 0.9900 ?
    C15' H15D . 0.9900 ?
    C16' C17' . 1.522(8) ?
    C16' H16C . 0.9900 ?
    C16' H16D . 0.9900 ?
    C17' C18' . 1.530(7) ?
    C17' H17C . 0.9900 ?
    C17' H17D . 0.9900 ?
    C18' C19' . 1.501(7) ?
    C18' H18C . 0.9900 ?
    C18' H18D . 0.9900 ?
    C19' H19C . 0.9900 ?
    C19' H19D . 0.9900 ?
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 O1 C5 . . 110.2(4) ?
    C14 N4 C19 . . 123.9(5) ?
    C14 N4 C15 . . 121.3(5) ?
    C19 N4 C15 . . 114.8(5) ?
    N1 C1 C2 . . 175.4(7) ?
    C6 C2 C3 . . 120.7(6) ?
    C6 C2 C1 . . 121.9(5) ?
    C3 C2 C1 . . 117.4(6) ?
    N2 C3 C2 . . 179.1(8) ?
    C11 C4 C7 . . 126.9(6) ?
    C11 C4 C5 . . 127.2(5) ?
    C7 C4 C5 . . 105.9(5) ?
    O1 C5 C4 . . 103.2(4) ?
    O1 C5 C8 . . 106.0(5) ?
    C4 C5 C8 . . 111.1(5) ?
    O1 C5 C9 . . 105.7(4) ?
    C4 C5 C9 . . 116.2(5) ?
    C8 C5 C9 . . 113.5(5) ?
    O1 C6 C2 . . 115.8(5) ?
    O1 C6 C7 . . 110.5(5) ?
    C2 C6 C7 . . 133.7(6) ?
    C6 C7 C10 . . 128.1(5) ?
    C6 C7 C4 . . 109.9(5) ?
    C10 C7 C4 . . 122.0(5) ?
    C5 C8 H8A . . 109.5 ?
    C5 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    C5 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    C5 C9 H9A . . 109.5 ?
    C5 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C5 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    N3 C10 C7 . . 176.2(6) ?
    C4 C11 C12 . . 125.3(6) no
    C4 C11 H11 . . 117.3 ?
    C12 C11 H11 . . 117.3 ?
    C13 C12 C11 . . 124.1(6) no
    C13 C12 H12 . . 118.0 ?
    C11 C12 H12 . . 118.0 ?
    C12 C13 C14 . . 118.4(6) ?
    C12 C13 H13 . . 120.8 ?
    C14 C13 H13 . . 120.8 ?
    N4 C14 C13 . . 127.5(6) ?
    N4 C14 H14 . . 116.3 ?
    C13 C14 H14 . . 116.3 ?
    N4 C15 C16 . . 109.8(5) ?
    N4 C15 H15A . . 109.7 ?
    C16 C15 H15A . . 109.7 ?
    N4 C15 H15B . . 109.7 ?
    C16 C15 H15B . . 109.7 ?
    H15A C15 H15B . . 108.2 ?
    C15 C16 C17 . . 110.3(5) ?
    C15 C16 H16A . . 109.6 ?
    C17 C16 H16A . . 109.6 ?
    C15 C16 H16B . . 109.6 ?
    C17 C16 H16B . . 109.6 ?
    H16A C16 H16B . . 108.1 ?
    C16 C17 C18 . . 109.8(5) ?
    C16 C17 H17A . . 109.7 ?
    C18 C17 H17A . . 109.7 ?
    C16 C17 H17B . . 109.7 ?
    C18 C17 H17B . . 109.7 ?
    H17A C17 H17B . . 108.2 ?
    C19 C18 C17 . . 110.8(5) ?
    C19 C18 H18A . . 109.5 ?
    C17 C18 H18A . . 109.5 ?
    C19 C18 H18B . . 109.5 ?
    C17 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 108.1 ?
    N4 C19 C18 . . 110.3(5) ?
    N4 C19 H19A . . 109.6 ?
    C18 C19 H19A . . 109.6 ?
    N4 C19 H19B . . 109.6 ?
    C18 C19 H19B . . 109.6 ?
    H19A C19 H19B . . 108.1 ?
    C6' O1' C5' . . 109.4(4) ?
    C14' N4' C15' . . 122.6(5) ?
    C14' N4' C19' . . 124.6(5) ?
    C15' N4' C19' . . 112.4(4) ?
    N1' C1' C2' . . 178.8(7) ?
    C6' C2' C3' . . 121.4(5) ?
    C6' C2' C1' . . 119.8(5) ?
    C3' C2' C1' . . 118.7(5) ?
    N2' C3' C2' . . 178.7(7) ?
    C11' C4' C7' . . 126.2(5) ?
    C11' C4' C5' . . 126.6(5) ?
    C7' C4' C5' . . 107.2(5) ?
    O1' C5' C9' . . 105.1(4) ?
    O1' C5' C4' . . 102.9(4) ?
    C9' C5' C4' . . 115.5(5) ?
    O1' C5' C8' . . 105.8(5) ?
    C9' C5' C8' . . 113.3(5) ?
    C4' C5' C8' . . 112.8(5) ?
    O1' C6' C7' . . 110.9(5) ?
    O1' C6' C2' . . 115.4(5) ?
    C7' C6' C2' . . 133.7(6) ?
    C6' C7' C10' . . 126.9(5) ?
    C6' C7' C4' . . 109.5(5) ?
    C10' C7' C4' . . 123.6(5) ?
    C5' C8' H8'A . . 109.5 ?
    C5' C8' H8'B . . 109.5 ?
    H8'A C8' H8'B . . 109.5 ?
    C5' C8' H8'C . . 109.5 ?
    H8'A C8' H8'C . . 109.5 ?
    H8'B C8' H8'C . . 109.5 ?
    C5' C9' H9'A . . 109.5 ?
    C5' C9' H9'B . . 109.5 ?
    H9'A C9' H9'B . . 109.5 ?
    C5' C9' H9'C . . 109.5 ?
    H9'A C9' H9'C . . 109.5 ?
    H9'B C9' H9'C . . 109.5 ?
    N3' C10' C7' . . 174.9(6) ?
    C4' C11' C12' . . 126.7(6) no
    C4' C11' H11' . . 116.7 ?
    C12' C11' H11' . . 116.7 ?
    C13' C12' C11' . . 122.9(6) no
    C13' C12' H12' . . 118.5 ?
    C11' C12' H12' . . 118.5 ?
    C12' C13' C14' . . 119.8(6) ?
    C12' C13' H13' . . 120.1 ?
    C14' C13' H13' . . 120.1 ?
    N4' C14' C13' . . 126.3(6) ?
    N4' C14' H14' . . 116.9 ?
    C13' C14' H14' . . 116.9 ?
    N4' C15' C16' . . 111.6(5) ?
    N4' C15' H15C . . 109.3 ?
    C16' C15' H15C . . 109.3 ?
    N4' C15' H15D . . 109.3 ?
    C16' C15' H15D . . 109.3 ?
    H15C C15' H15D . . 108.0 ?
    C15' C16' C17' . . 110.2(5) ?
    C15' C16' H16C . . 109.6 ?
    C17' C16' H16C . . 109.6 ?
    C15' C16' H16D . . 109.6 ?
    C17' C16' H16D . . 109.6 ?
    H16C C16' H16D . . 108.1 ?
    C16' C17' C18' . . 110.6(5) ?
    C16' C17' H17C . . 109.5 ?
    C18' C17' H17C . . 109.5 ?
    C16' C17' H17D . . 109.5 ?
    C18' C17' H17D . . 109.5 ?
    H17C C17' H17D . . 108.1 ?
    C19' C18' C17' . . 110.6(5) ?
    C19' C18' H18C . . 109.5 ?
    C17' C18' H18C . . 109.5 ?
    C19' C18' H18D . . 109.5 ?
    C17' C18' H18D . . 109.5 ?
    H18C C18' H18D . . 108.1 ?
    N4' C19' C18' . . 109.6(4) ?
    N4' C19' H19C . . 109.8 ?
    C18' C19' H19C . . 109.8 ?
    N4' C19' H19D . . 109.8 ?
    C18' C19' H19D . . 109.8 ?
    H19C C19' H19D . . 108.2 ?
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
    C6 O1 C5 C4 . . . . 5.6(5) ?
    C6 O1 C5 C8 . . . . -111.2(5) ?
    C6 O1 C5 C9 . . . . 128.1(5) ?
    C11 C4 C5 O1 . . . . 174.9(5) ?
    C7 C4 C5 O1 . . . . -5.7(6) ?
    C11 C4 C5 C8 . . . . -71.9(7) ?
    C7 C4 C5 C8 . . . . 107.4(5) ?
    C11 C4 C5 C9 . . . . 59.8(7) ?
    C7 C4 C5 C9 . . . . -120.8(5) ?
    C5 O1 C6 C2 . . . . 177.3(5) ?
    C5 O1 C6 C7 . . . . -3.3(6) ?
    C3 C2 C6 O1 . . . . 0.9(8) ?
    C1 C2 C6 O1 . . . . -176.6(5) ?
    C3 C2 C6 C7 . . . . -178.2(6) ?
    C1 C2 C6 C7 . . . . 4.3(11) ?
    O1 C6 C7 C10 . . . . 179.1(5) ?
    C2 C6 C7 C10 . . . . -1.7(11) ?
    O1 C6 C7 C4 . . . . -0.6(7) ?
    C2 C6 C7 C4 . . . . 178.5(6) ?
    C11 C4 C7 C6 . . . . -176.5(5) ?
    C5 C4 C7 C6 . . . . 4.1(7) ?
    C11 C4 C7 C10 . . . . 3.8(10) ?
    C5 C4 C7 C10 . . . . -175.6(5) ?
    C7 C4 C11 C12 . . . . -174.8(6) no
    C5 C4 C11 C12 . . . . 4.4(10) ?
    C4 C11 C12 C13 . . . . 179.1(5) ?
    C11 C12 C13 C14 . . . . -177.9(6) ?
    C19 N4 C14 C13 . . . . 1.9(10) ?
    C15 N4 C14 C13 . . . . -176.8(6) ?
    C12 C13 C14 N4 . . . . -174.1(5) ?
    C14 N4 C15 C16 . . . . 121.5(6) ?
    C19 N4 C15 C16 . . . . -57.3(6) ?
    N4 C15 C16 C17 . . . . 57.2(7) ?
    C15 C16 C17 C18 . . . . -57.4(7) ?
    C16 C17 C18 C19 . . . . 55.7(7) ?
    C14 N4 C19 C18 . . . . -123.2(6) ?
    C15 N4 C19 C18 . . . . 55.5(7) ?
    C17 C18 C19 N4 . . . . -53.5(7) ?
    C6' O1' C5' C9' . . . . -121.2(5) ?
    C6' O1' C5' C4' . . . . 0.1(6) ?
    C6' O1' C5' C8' . . . . 118.7(5) ?
    C11' C4' C5' O1' . . . . -178.6(5) ?
    C7' C4' C5' O1' . . . . 1.6(6) ?
    C11' C4' C5' C9' . . . . -64.7(8) ?
    C7' C4' C5' C9' . . . . 115.5(5) ?
    C11' C4' C5' C8' . . . . 67.9(8) ?
    C7' C4' C5' C8' . . . . -112.0(5) ?
    C5' O1' C6' C7' . . . . -1.7(7) ?
    C5' O1' C6' C2' . . . . 176.7(5) ?
    C3' C2' C6' O1' . . . . -0.9(8) ?
    C1' C2' C6' O1' . . . . -176.6(5) ?
    C3' C2' C6' C7' . . . . 177.0(7) ?
    C1' C2' C6' C7' . . . . 1.3(11) ?
    O1' C6' C7' C10' . . . . -177.2(5) ?
    C2' C6' C7' C10' . . . . 4.8(11) ?
    O1' C6' C7' C4' . . . . 2.8(7) ?
    C2' C6' C7' C4' . . . . -175.2(6) ?
    C11' C4' C7' C6' . . . . 177.5(6) ?
    C5' C4' C7' C6' . . . . -2.7(6) ?
    C11' C4' C7' C10' . . . . -2.5(10) ?
    C5' C4' C7' C10' . . . . 177.3(5) ?
    C7' C4' C11' C12' . . . . -177.9(6) no
    C5' C4' C11' C12' . . . . 2.3(10) ?
    C4' C11' C12' C13' . . . . 177.1(6) ?
    C11' C12' C13' C14' . . . . -179.4(5) ?
    C15' N4' C14' C13' . . . . 173.0(6) ?
    C19' N4' C14' C13' . . . . 0.6(10) ?
    C12' C13' C14' N4' . . . . 177.6(5) ?
    C14' N4' C15' C16' . . . . -115.0(6) ?
    C19' N4' C15' C16' . . . . 58.3(7) ?
    N4' C15' C16' C17' . . . . -55.0(7) ?
    C15' C16' C17' C18' . . . . 53.9(7) ?
    C16' C17' C18' C19' . . . . -55.8(7) ?
    C14' N4' C19' C18' . . . . 114.3(6) ?
    C15' N4' C19' C18' . . . . -58.9(7) ?
    C17' C18' C19' N4' . . . . 57.2(7) ?
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
    C13' H13' N2 2_645 0.95 2.49 3.324(8) 147 yes
    C14 H14 N1' . 0.95 2.58 3.498(8) 161 yes
    C14' H14' N1 4_475 0.95 2.61 3.484(8) 153 yes
    C16' H16D N2 4_475 0.99 2.55 3.477(8) 156 yes
    C19 H19A N2' 2_646 0.99 2.60 3.568(8) 166 yes
