#------------------------------------------------------------------------------
#$Date: 2022-09-23 03:45:29 +0300 (Fri, 23 Sep 2022) $
#$Revision: 278100 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/88/7158890.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7158890
loop_
_publ_author_name
'Jiang, Yitian'
'Liu, Miaochang'
'Wang, Mengzhu'
'Lei, yunxiang'
'Ding, Qiuping'
'Wu, Huayue'
'Huang, Xiaobo'
_publ_section_title
;
 Unexpected synthesis, delayed emission and solid-state acidochromism of
 novel 2,7-naphthyridine derivatives obtained from
 2-(3,5-diaryl-4H-pyran-4-ylidene)malononitrile
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01336C
_journal_year                    2022
_chemical_formula_sum            'C48 H40 N4'
_chemical_formula_weight         672.84
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2022-05-19 deposited with the CCDC.	2022-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.793(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.9851(13)
_cell_length_b                   9.8420(7)
_cell_length_c                   19.9967(16)
_cell_measurement_reflns_used    3886
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      51.797
_cell_measurement_theta_min      4.712
_cell_volume                     3557.7(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0819
_diffrn_reflns_av_unetI/netI     0.0937
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16646
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         2.253
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0157(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     480
_refine_ls_number_reflns         6568
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0603
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0473P)²+0.8025P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1634
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4244
_reflns_number_total             6568
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01336c2.cif
_cod_data_source_block           mo_ddz21105_0m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7158890
_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. 
;
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.996
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.26097(11) 0.4877(2) 0.52957(11) 0.0406(5) Uani 1 1 d . . . . .
N2 N 0.47486(11) 0.19436(19) 0.56686(10) 0.0370(5) Uani 1 1 d . . . . .
N3 N 0.31026(13) 0.3707(2) 0.63710(12) 0.0496(6) Uani 1 1 d D . . . .
N4 N 0.42110(12) 0.2073(2) 0.65363(11) 0.0400(5) Uani 1 1 d D . . . .
C1 C 0.31117(13) 0.3984(2) 0.57366(13) 0.0372(6) Uani 1 1 d . . . . .
C2 C 0.36663(13) 0.3379(2) 0.54622(12) 0.0318(5) Uani 1 1 d . . . . .
C3 C 0.42090(13) 0.2467(2) 0.58847(12) 0.0332(6) Uani 1 1 d . . . . .
C4 C 0.47762(13) 0.2262(2) 0.50232(13) 0.0358(6) Uani 1 1 d . . . . .
C5 C 0.42671(12) 0.3097(2) 0.45558(12) 0.0315(5) Uani 1 1 d . . . . .
C6 C 0.36953(12) 0.3690(2) 0.47788(12) 0.0304(5) Uani 1 1 d . . . . .
C7 C 0.31416(13) 0.4633(2) 0.43569(12) 0.0349(6) Uani 1 1 d . . . . .
C8 C 0.26348(14) 0.5205(3) 0.46264(13) 0.0401(6) Uani 1 1 d . . . . .
C9 C 0.20819(16) 0.6237(3) 0.42270(15) 0.0596(8) Uani 1 1 d . . . . .
H9A H 0.1590 0.5843 0.4093 0.089 Uiso 1 1 calc R U . . .
H9B H 0.2203 0.6509 0.3809 0.089 Uiso 1 1 calc R U . . .
H9C H 0.2096 0.7026 0.4522 0.089 Uiso 1 1 calc R U . . .
C10 C 0.54167(15) 0.1613(3) 0.48469(14) 0.0502(7) Uani 1 1 d . . . . .
H10A H 0.5783 0.2301 0.4847 0.075 Uiso 1 1 calc R U . . .
H10B H 0.5241 0.1197 0.4386 0.075 Uiso 1 1 calc R U . . .
H10C H 0.5638 0.0924 0.5194 0.075 Uiso 1 1 calc R U . . .
C11 C 0.20544(14) 0.5492(3) 0.55765(14) 0.0493(7) Uani 1 1 d . . . . .
H11A H 0.1850 0.4785 0.5809 0.059 Uiso 1 1 calc R U . . .
H11B H 0.1649 0.5848 0.5185 0.059 Uiso 1 1 calc R U . . .
C12 C 0.23576(14) 0.6632(3) 0.60955(14) 0.0457(7) Uani 1 1 d . . . . .
C13 C 0.29432(17) 0.7422(3) 0.60661(16) 0.0618(8) Uani 1 1 d . . . . .
H13 H 0.3185 0.7225 0.5732 0.074 Uiso 1 1 calc R U . . .
C14 C 0.3182(2) 0.8503(3) 0.65204(17) 0.0716(9) Uani 1 1 d . . . . .
H14 H 0.3584 0.9035 0.6494 0.086 Uiso 1 1 calc R U . . .
C15 C 0.2834(2) 0.8798(4) 0.70073(19) 0.0851(11) Uani 1 1 d . . . . .
H15 H 0.2988 0.9541 0.7312 0.102 Uiso 1 1 calc R U . . .
C16 C 0.2257(2) 0.8002(5) 0.7046(2) 0.0921(13) Uani 1 1 d . . . . .
H16 H 0.2017 0.8199 0.7382 0.111 Uiso 1 1 calc R U . . .
C17 C 0.20241(17) 0.6919(4) 0.66002(16) 0.0675(9) Uani 1 1 d . . . . .
H17 H 0.1634 0.6370 0.6640 0.081 Uiso 1 1 calc R U . . .
C18 C 0.47967(14) 0.1238(2) 0.69784(13) 0.0420(6) Uani 1 1 d . . . . .
H18A H 0.5274 0.1564 0.6949 0.050 Uiso 1 1 calc R U . . .
H18B H 0.4731 0.0300 0.6806 0.050 Uiso 1 1 calc R U . . .
C19 C 0.48045(13) 0.1262(2) 0.77305(13) 0.0371(6) Uani 1 1 d . . . . .
C20 C 0.48038(15) 0.2473(3) 0.80825(14) 0.0468(7) Uani 1 1 d . . . . .
H20 H 0.4766 0.3300 0.7838 0.056 Uiso 1 1 calc R U . . .
C21 C 0.48581(16) 0.2484(3) 0.87849(15) 0.0553(8) Uani 1 1 d . . . . .
H21 H 0.4856 0.3317 0.9015 0.066 Uiso 1 1 calc R U . . .
C22 C 0.49157(16) 0.1283(3) 0.91551(15) 0.0560(8) Uani 1 1 d . . . . .
H22 H 0.4964 0.1292 0.9637 0.067 Uiso 1 1 calc R U . . .
C23 C 0.49013(17) 0.0077(3) 0.88079(15) 0.0579(8) Uani 1 1 d . . . . .
H23 H 0.4929 -0.0748 0.9052 0.069 Uiso 1 1 calc R U . . .
C24 C 0.48459(16) 0.0063(3) 0.81034(14) 0.0490(7) Uani 1 1 d . . . . .
H24 H 0.4836 -0.0773 0.7873 0.059 Uiso 1 1 calc R U . . .
C25 C 0.30655(13) 0.4940(2) 0.36034(13) 0.0349(6) Uani 1 1 d . . . . .
C26 C 0.25229(14) 0.4276(3) 0.30801(13) 0.0446(7) Uani 1 1 d . . . . .
H26 H 0.2213 0.3647 0.3206 0.054 Uiso 1 1 calc R U . . .
C27 C 0.24283(14) 0.4520(3) 0.23792(14) 0.0447(7) Uani 1 1 d . . . . .
H27 H 0.2054 0.4053 0.2039 0.054 Uiso 1 1 calc R U . . .
C28 C 0.28683(13) 0.5430(2) 0.21617(13) 0.0365(6) Uani 1 1 d . . . . .
C29 C 0.34038(14) 0.6122(2) 0.26906(13) 0.0405(6) Uani 1 1 d . . . . .
H29 H 0.3710 0.6759 0.2564 0.049 Uiso 1 1 calc R U . . .
C30 C 0.34942(14) 0.5891(2) 0.33937(13) 0.0400(6) Uani 1 1 d . . . . .
H30 H 0.3852 0.6388 0.3735 0.048 Uiso 1 1 calc R U . . .
C31 C 0.27804(13) 0.5641(2) 0.13842(13) 0.0352(6) Uani 1 1 d . U . . .
C32 C 0.22069(18) 0.5104(3) 0.08878(15) 0.0608(8) Uani 1 1 d . . . . .
H32 H 0.1847 0.4614 0.1022 0.073 Uiso 1 1 calc R U . . .
C33 C 0.21317(17) 0.5253(3) 0.01845(15) 0.0638(9) Uani 1 1 d . . . . .
H33 H 0.1727 0.4853 -0.0153 0.077 Uiso 1 1 calc R U . . .
C34 C 0.26452(17) 0.5984(3) -0.00286(16) 0.0562(8) Uani 1 1 d . . . . .
H34 H 0.2602 0.6067 -0.0508 0.067 Uiso 1 1 calc R U . . .
C35 C 0.32176(16) 0.6585(3) 0.04702(16) 0.0568(8) Uani 1 1 d . . . . .
H35 H 0.3561 0.7122 0.0336 0.068 Uiso 1 1 calc R U . . .
C36 C 0.32914(16) 0.6400(3) 0.11813(15) 0.0549(8) Uani 1 1 d . U . . .
H36 H 0.3693 0.6796 0.1524 0.066 Uiso 1 1 calc R U . . .
C37 C 0.44053(13) 0.3314(2) 0.38615(12) 0.0318(6) Uani 1 1 d . . . . .
C38 C 0.40360(13) 0.2579(2) 0.32678(13) 0.0376(6) Uani 1 1 d . . . . .
H38 H 0.3651 0.1989 0.3280 0.045 Uiso 1 1 calc R U . . .
C39 C 0.42272(14) 0.2704(2) 0.26551(13) 0.0390(6) Uani 1 1 d . . . . .
H39 H 0.3961 0.2209 0.2256 0.047 Uiso 1 1 calc R U . . .
C40 C 0.48040(13) 0.3544(2) 0.26164(13) 0.0337(6) Uani 1 1 d . . . . .
C41 C 0.51791(14) 0.4272(2) 0.32161(13) 0.0387(6) Uani 1 1 d . . . . .
H41 H 0.5572 0.4845 0.3209 0.046 Uiso 1 1 calc R U . . .
C42 C 0.49785(13) 0.4158(2) 0.38234(12) 0.0357(6) Uani 1 1 d . . . . .
H42 H 0.5237 0.4666 0.4221 0.043 Uiso 1 1 calc R U . . .
C43 C 0.50259(14) 0.3646(2) 0.19504(13) 0.0344(6) Uani 1 1 d . . . . .
C44 C 0.57655(16) 0.3740(3) 0.19943(15) 0.0506(7) Uani 1 1 d . . . . .
H44 H 0.6129 0.3766 0.2436 0.061 Uiso 1 1 calc R U . . .
C45 C 0.59716(18) 0.3796(3) 0.13850(17) 0.0604(9) Uani 1 1 d . . . . .
H45 H 0.6474 0.3855 0.1413 0.072 Uiso 1 1 calc R U . . .
C46 C 0.5436(2) 0.3765(3) 0.07396(17) 0.0587(8) Uani 1 1 d . . . . .
H46 H 0.5573 0.3807 0.0327 0.070 Uiso 1 1 calc R U . . .
C47 C 0.47077(19) 0.3674(3) 0.06971(15) 0.0546(8) Uani 1 1 d . . . . .
H47 H 0.4344 0.3648 0.0256 0.066 Uiso 1 1 calc R U . . .
C48 C 0.45000(16) 0.3618(2) 0.13122(14) 0.0458(7) Uani 1 1 d . . . . .
H48 H 0.3997 0.3561 0.1283 0.055 Uiso 1 1 calc R U . . .
H3 H 0.2765(12) 0.418(2) 0.6464(14) 0.056(8) Uiso 1 1 d D . . . .
H4 H 0.3875(12) 0.248(2) 0.6682(12) 0.047(8) Uiso 1 1 d D . . . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C1 122.46(19) . . ?
C8 N1 C11 120.8(2) . . ?
C1 N1 C11 116.7(2) . . ?
C3 N2 C4 118.7(2) . . ?
C1 N3 H3 109.3(18) . . ?
C3 N4 C18 121.66(19) . . ?
C3 N4 H4 113.6(16) . . ?
C18 N4 H4 124.0(16) . . ?
N3 C1 N1 122.5(2) . . ?
N3 C1 C2 120.5(2) . . ?
N1 C1 C2 116.9(2) . . ?
C6 C2 C3 118.12(19) . . ?
C6 C2 C1 121.4(2) . . ?
C3 C2 C1 120.5(2) . . ?
N2 C3 N4 115.1(2) . . ?
N2 C3 C2 122.5(2) . . ?
N4 C3 C2 122.39(19) . . ?
N2 C4 C5 124.1(2) . . ?
N2 C4 C10 113.3(2) . . ?
C5 C4 C10 122.6(2) . . ?
C4 C5 C6 118.3(2) . . ?
C4 C5 C37 115.03(19) . . ?
C6 C5 C37 126.7(2) . . ?
C2 C6 C5 118.2(2) . . ?
C2 C6 C7 117.43(19) . . ?
C5 C6 C7 124.3(2) . . ?
C8 C7 C6 120.3(2) . . ?
C8 C7 C25 116.9(2) . . ?
C6 C7 C25 122.66(19) . . ?
C7 C8 N1 121.4(2) . . ?
C7 C8 C9 122.2(2) . . ?
N1 C8 C9 116.4(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 113.6(2) . . ?
N1 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
N1 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C17 118.4(3) . . ?
C13 C12 C11 122.2(2) . . ?
C17 C12 C11 119.4(3) . . ?
C12 C13 C14 121.0(3) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 119.3(3) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C17 120.8(3) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C12 120.5(3) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
N4 C18 C19 112.0(2) . . ?
N4 C18 H18A 109.2 . . ?
C19 C18 H18A 109.2 . . ?
N4 C18 H18B 109.2 . . ?
C19 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C20 C19 C24 117.9(2) . . ?
C20 C19 C18 121.5(2) . . ?
C24 C19 C18 120.5(2) . . ?
C21 C20 C19 120.9(2) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C20 C21 C22 120.6(3) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C23 C22 C21 118.9(3) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C22 C23 C24 120.6(3) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C19 121.0(3) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?
C30 C25 C26 117.3(2) . . ?
C30 C25 C7 123.7(2) . . ?
C26 C25 C7 119.0(2) . . ?
C27 C26 C25 121.4(2) . . ?
C27 C26 H26 119.3 . . ?
C25 C26 H26 119.3 . . ?
C26 C27 C28 121.9(2) . . ?
C26 C27 H27 119.0 . . ?
C28 C27 H27 119.0 . . ?
C27 C28 C29 116.5(2) . . ?
C27 C28 C31 121.3(2) . . ?
C29 C28 C31 122.1(2) . . ?
C30 C29 C28 121.7(2) . . ?
C30 C29 H29 119.2 . . ?
C28 C29 H29 119.2 . . ?
C29 C30 C25 121.1(2) . . ?
C29 C30 H30 119.5 . . ?
C25 C30 H30 119.5 . . ?
C32 C31 C36 118.8(3) . . ?
C32 C31 C28 120.9(2) . . ?
C36 C31 C28 120.3(2) . . ?
C31 C32 C33 121.5(3) . . ?
C31 C32 H32 119.2 . . ?
C33 C32 H32 119.2 . . ?
C32 C33 C34 120.5(3) . . ?
C32 C33 H33 119.7 . . ?
C34 C33 H33 119.7 . . ?
C35 C34 C33 118.7(3) . . ?
C35 C34 H34 120.7 . . ?
C33 C34 H34 120.7 . . ?
C34 C35 C36 119.8(3) . . ?
C34 C35 H35 120.1 . . ?
C36 C35 H35 120.1 . . ?
C31 C36 C35 120.6(3) . . ?
C31 C36 H36 119.7 . . ?
C35 C36 H36 119.7 . . ?
C38 C37 C42 117.7(2) . . ?
C38 C37 C5 122.1(2) . . ?
C42 C37 C5 119.7(2) . . ?
C37 C38 C39 120.8(2) . . ?
C37 C38 H38 119.6 . . ?
C39 C38 H38 119.6 . . ?
C38 C39 C40 121.6(2) . . ?
C38 C39 H39 119.2 . . ?
C40 C39 H39 119.2 . . ?
C41 C40 C39 117.5(2) . . ?
C41 C40 C43 121.1(2) . . ?
C39 C40 C43 121.4(2) . . ?
C42 C41 C40 120.6(2) . . ?
C42 C41 H41 119.7 . . ?
C40 C41 H41 119.7 . . ?
C41 C42 C37 121.8(2) . . ?
C41 C42 H42 119.1 . . ?
C37 C42 H42 119.1 . . ?
C48 C43 C44 120.1(2) . . ?
C48 C43 C40 120.1(2) . . ?
C44 C43 C40 119.8(2) . . ?
C43 C44 C45 120.0(3) . . ?
C43 C44 H44 120.0 . . ?
C45 C44 H44 120.0 . . ?
C46 C45 C44 119.7(3) . . ?
C46 C45 H45 120.2 . . ?
C44 C45 H45 120.2 . . ?
C47 C46 C45 120.3(3) . . ?
C47 C46 H46 119.8 . . ?
C45 C46 H46 119.8 . . ?
C46 C47 C48 120.0(3) . . ?
C46 C47 H47 120.0 . . ?
C48 C47 H47 120.0 . . ?
C43 C48 C47 120.0(3) . . ?
C43 C48 H48 120.0 . . ?
C47 C48 H48 120.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C8 1.392(3) . ?
N1 C1 1.394(3) . ?
N1 C11 1.468(3) . ?
N2 C3 1.331(3) . ?
N2 C4 1.345(3) . ?
N3 C1 1.303(3) . ?
N3 H3 0.858(16) . ?
N4 C3 1.358(3) . ?
N4 C18 1.447(3) . ?
N4 H4 0.875(16) . ?
C1 C2 1.455(3) . ?
C2 C6 1.418(3) . ?
C2 C3 1.432(3) . ?
C4 C5 1.389(3) . ?
C4 C10 1.508(3) . ?
C5 C6 1.419(3) . ?
C5 C37 1.505(3) . ?
C6 C7 1.461(3) . ?
C7 C8 1.360(3) . ?
C7 C25 1.500(3) . ?
C8 C9 1.503(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C11 C12 1.517(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C12 C13 1.373(4) . ?
C12 C17 1.375(3) . ?
C13 C14 1.383(4) . ?
C13 H13 0.9400 . ?
C14 C15 1.365(5) . ?
C14 H14 0.9400 . ?
C15 C16 1.367(5) . ?
C15 H15 0.9400 . ?
C16 C17 1.374(5) . ?
C16 H16 0.9400 . ?
C17 H17 0.9400 . ?
C18 C19 1.500(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C19 C20 1.385(3) . ?
C19 C24 1.385(3) . ?
C20 C21 1.377(3) . ?
C20 H20 0.9400 . ?
C21 C22 1.382(4) . ?
C21 H21 0.9400 . ?
C22 C23 1.371(4) . ?
C22 H22 0.9400 . ?
C23 C24 1.380(4) . ?
C23 H23 0.9400 . ?
C24 H24 0.9400 . ?
C25 C30 1.387(3) . ?
C25 C26 1.387(3) . ?
C26 C27 1.379(3) . ?
C26 H26 0.9400 . ?
C27 C28 1.383(3) . ?
C27 H27 0.9400 . ?
C28 C29 1.399(3) . ?
C28 C31 1.526(3) . ?
C29 C30 1.382(3) . ?
C29 H29 0.9400 . ?
C30 H30 0.9400 . ?
C31 C32 1.338(4) . ?
C31 C36 1.380(3) . ?
C32 C33 1.377(4) . ?
C32 H32 0.9400 . ?
C33 C34 1.380(4) . ?
C33 H33 0.9400 . ?
C34 C35 1.365(4) . ?
C34 H34 0.9400 . ?
C35 C36 1.398(4) . ?
C35 H35 0.9400 . ?
C36 H36 0.9400 . ?
C37 C38 1.384(3) . ?
C37 C42 1.390(3) . ?
C38 C39 1.385(3) . ?
C38 H38 0.9400 . ?
C39 C40 1.393(3) . ?
C39 H39 0.9400 . ?
C40 C41 1.391(3) . ?
C40 C43 1.518(3) . ?
C41 C42 1.384(3) . ?
C41 H41 0.9400 . ?
C42 H42 0.9400 . ?
C43 C48 1.359(4) . ?
C43 C44 1.383(3) . ?
C44 C45 1.390(3) . ?
C44 H44 0.9400 . ?
C45 C46 1.378(4) . ?
C45 H45 0.9400 . ?
C46 C47 1.361(4) . ?
C46 H46 0.9400 . ?
C47 C48 1.403(3) . ?
C47 H47 0.9400 . ?
C48 H48 0.9400 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4 N3 0.875(16) 1.85(2) 2.588(3) 140(2) .
N4 H4 N3 0.875(16) 1.85(2) 2.588(3) 140(2) .
N4 H4 N3 0.875(16) 1.85(2) 2.588(3) 140(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 N3 177.9(2) . . . . ?
C11 N1 C1 N3 -0.7(4) . . . . ?
C8 N1 C1 C2 -1.0(3) . . . . ?
C11 N1 C1 C2 -179.6(2) . . . . ?
N3 C1 C2 C6 -178.6(2) . . . . ?
N1 C1 C2 C6 0.3(3) . . . . ?
N3 C1 C2 C3 0.2(4) . . . . ?
N1 C1 C2 C3 179.1(2) . . . . ?
C4 N2 C3 N4 178.7(2) . . . . ?
C4 N2 C3 C2 -1.4(3) . . . . ?
C18 N4 C3 N2 5.0(3) . . . . ?
C18 N4 C3 C2 -175.0(2) . . . . ?
C6 C2 C3 N2 2.3(3) . . . . ?
C1 C2 C3 N2 -176.6(2) . . . . ?
C6 C2 C3 N4 -177.7(2) . . . . ?
C1 C2 C3 N4 3.4(3) . . . . ?
C3 N2 C4 C5 -1.0(4) . . . . ?
C3 N2 C4 C10 179.5(2) . . . . ?
N2 C4 C5 C6 2.3(4) . . . . ?
C10 C4 C5 C6 -178.3(2) . . . . ?
N2 C4 C5 C37 -179.9(2) . . . . ?
C10 C4 C5 C37 -0.5(3) . . . . ?
C3 C2 C6 C5 -0.9(3) . . . . ?
C1 C2 C6 C5 177.9(2) . . . . ?
C3 C2 C6 C7 -179.5(2) . . . . ?
C1 C2 C6 C7 -0.6(3) . . . . ?
C4 C5 C6 C2 -1.2(3) . . . . ?
C37 C5 C6 C2 -178.7(2) . . . . ?
C4 C5 C6 C7 177.2(2) . . . . ?
C37 C5 C6 C7 -0.3(4) . . . . ?
C2 C6 C7 C8 1.6(3) . . . . ?
C5 C6 C7 C8 -176.8(2) . . . . ?
C2 C6 C7 C25 -173.9(2) . . . . ?
C5 C6 C7 C25 7.7(4) . . . . ?
C6 C7 C8 N1 -2.4(4) . . . . ?
C25 C7 C8 N1 173.4(2) . . . . ?
C6 C7 C8 C9 176.6(2) . . . . ?
C25 C7 C8 C9 -7.6(4) . . . . ?
C1 N1 C8 C7 2.1(4) . . . . ?
C11 N1 C8 C7 -179.3(2) . . . . ?
C1 N1 C8 C9 -176.9(2) . . . . ?
C11 N1 C8 C9 1.7(4) . . . . ?
C8 N1 C11 C12 -102.0(3) . . . . ?
C1 N1 C11 C12 76.6(3) . . . . ?
N1 C11 C12 C13 28.5(4) . . . . ?
N1 C11 C12 C17 -153.6(3) . . . . ?
C17 C12 C13 C14 -1.6(5) . . . . ?
C11 C12 C13 C14 176.3(3) . . . . ?
C12 C13 C14 C15 -0.1(5) . . . . ?
C13 C14 C15 C16 1.1(6) . . . . ?
C14 C15 C16 C17 -0.4(6) . . . . ?
C15 C16 C17 C12 -1.3(6) . . . . ?
C13 C12 C17 C16 2.3(5) . . . . ?
C11 C12 C17 C16 -175.7(3) . . . . ?
C3 N4 C18 C19 163.6(2) . . . . ?
N4 C18 C19 C20 -51.4(3) . . . . ?
N4 C18 C19 C24 131.5(3) . . . . ?
C24 C19 C20 C21 1.3(4) . . . . ?
C18 C19 C20 C21 -175.9(2) . . . . ?
C19 C20 C21 C22 0.1(4) . . . . ?
C20 C21 C22 C23 -1.5(5) . . . . ?
C21 C22 C23 C24 1.4(5) . . . . ?
C22 C23 C24 C19 0.1(5) . . . . ?
C20 C19 C24 C23 -1.4(4) . . . . ?
C18 C19 C24 C23 175.8(3) . . . . ?
C8 C7 C25 C30 101.0(3) . . . . ?
C6 C7 C25 C30 -83.3(3) . . . . ?
C8 C7 C25 C26 -76.9(3) . . . . ?
C6 C7 C25 C26 98.8(3) . . . . ?
C30 C25 C26 C27 2.0(4) . . . . ?
C7 C25 C26 C27 180.0(2) . . . . ?
C25 C26 C27 C28 0.2(4) . . . . ?
C26 C27 C28 C29 -1.7(4) . . . . ?
C26 C27 C28 C31 177.1(2) . . . . ?
C27 C28 C29 C30 0.9(4) . . . . ?
C31 C28 C29 C30 -177.9(2) . . . . ?
C28 C29 C30 C25 1.4(4) . . . . ?
C26 C25 C30 C29 -2.7(3) . . . . ?
C7 C25 C30 C29 179.3(2) . . . . ?
C27 C28 C31 C32 9.9(4) . . . . ?
C29 C28 C31 C32 -171.4(3) . . . . ?
C27 C28 C31 C36 -170.6(2) . . . . ?
C29 C28 C31 C36 8.2(3) . . . . ?
C36 C31 C32 C33 2.3(4) . . . . ?
C28 C31 C32 C33 -178.1(3) . . . . ?
C31 C32 C33 C34 -1.0(5) . . . . ?
C32 C33 C34 C35 -1.7(5) . . . . ?
C33 C34 C35 C36 2.9(4) . . . . ?
C32 C31 C36 C35 -1.1(4) . . . . ?
C28 C31 C36 C35 179.4(2) . . . . ?
C34 C35 C36 C31 -1.5(4) . . . . ?
C4 C5 C37 C38 98.2(3) . . . . ?
C6 C5 C37 C38 -84.2(3) . . . . ?
C4 C5 C37 C42 -74.1(3) . . . . ?
C6 C5 C37 C42 103.5(3) . . . . ?
C42 C37 C38 C39 -1.0(4) . . . . ?
C5 C37 C38 C39 -173.5(2) . . . . ?
C37 C38 C39 C40 1.4(4) . . . . ?
C38 C39 C40 C41 -0.7(4) . . . . ?
C38 C39 C40 C43 178.2(2) . . . . ?
C39 C40 C41 C42 -0.3(4) . . . . ?
C43 C40 C41 C42 -179.2(2) . . . . ?
C40 C41 C42 C37 0.6(4) . . . . ?
C38 C37 C42 C41 0.0(4) . . . . ?
C5 C37 C42 C41 172.7(2) . . . . ?
C41 C40 C43 C48 -143.6(2) . . . . ?
C39 C40 C43 C48 37.5(3) . . . . ?
C41 C40 C43 C44 37.7(3) . . . . ?
C39 C40 C43 C44 -141.2(2) . . . . ?
C48 C43 C44 C45 -0.4(4) . . . . ?
C40 C43 C44 C45 178.2(2) . . . . ?
C43 C44 C45 C46 0.3(4) . . . . ?
C44 C45 C46 C47 -0.3(4) . . . . ?
C45 C46 C47 C48 0.3(4) . . . . ?
C44 C43 C48 C47 0.5(4) . . . . ?
C40 C43 C48 C47 -178.2(2) . . . . ?
C46 C47 C48 C43 -0.4(4) . . . . ?
