#------------------------------------------------------------------------------
#$Date: 2023-07-05 13:06:01 +0300 (Wed, 05 Jul 2023) $
#$Revision: 284914 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/67/7246739.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_7246739
loop_
_publ_author_name
'Liu, Miaochang'
'Xu, Xinyue'
'Chen, Yating'
'Ding, Qiuping'
'Lei, Yunxiang'
'Wu, Huayue'
'Huang, Xiaobo'
_publ_section_title
;
 Crystal structures, dual-state emissions and polymer-based doped
 room-temperature phosphorescence of 8-benzyloxyisoquinoline derivatives
;
_journal_issue                   22
_journal_name_full               CrystEngComm
_journal_page_first              3264
_journal_page_last               3270
_journal_paper_doi               10.1039/D3CE00231D
_journal_volume                  25
_journal_year                    2023
_chemical_absolute_configuration unk
_chemical_formula_sum            'C24 H24 N4 O3'
_chemical_formula_weight         416.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2023-03-03 deposited with the CCDC.	2023-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.254(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7300(9)
_cell_length_b                   13.6341(10)
_cell_length_c                   14.8150(14)
_cell_measurement_reflns_used    3638
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      48.498
_cell_measurement_theta_min      4.831
_cell_volume                     2167.3(3)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.991
_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  0.0199
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10438
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         2.349
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
; 
 Flack x determined using 1862 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.8(8)
_refine_ls_extinction_coef       0.039(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     564
_refine_ls_number_reflns         7518
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0487
_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)+(0.0474P)²+0.1028P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1224
_reflns_Friedel_coverage         0.798
_reflns_Friedel_fraction_full    0.867
_reflns_Friedel_fraction_max     0.865
_reflns_number_gt                5255
_reflns_number_total             7518
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00231d2.cif
_cod_data_source_block           mo_dd18245_0m
_cod_depositor_comments
'Adding full bibliography for 7246730--7246739.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7246739
_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   0.984
_shelx_estimated_absorpt_t_max   0.989
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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 1.0425(3) 0.0865(3) 0.0320(2) 0.0634(9) Uani 1 1 d . . . . .
N2 N 0.9942(3) 0.0239(3) 0.1731(2) 0.0636(10) Uani 1 1 d . . . . .
N3 N 0.4419(4) 0.0994(5) 0.2338(4) 0.1200(19) Uani 1 1 d . . . . .
N4 N 0.8352(5) 0.1214(3) 0.6469(3) 0.0794(12) Uani 1 1 d . . . . .
N5 N 0.7183(3) 0.3987(2) 0.1627(2) 0.0578(9) Uani 1 1 d . . . . .
N6 N 0.6669(3) 0.4551(2) 0.3049(2) 0.0525(8) Uani 1 1 d . . . . .
N7 N 0.1176(4) 0.3589(4) 0.3672(4) 0.1156(19) Uani 1 1 d . . . . .
N8 N 0.4680(6) 0.3272(4) 0.7845(4) 0.1031(16) Uani 1 1 d . . . . .
O1 O 0.7490(2) 0.06872(19) 0.22568(19) 0.0613(7) Uani 1 1 d . . . . .
O2 O 0.9339(4) 0.1465(4) 0.6810(3) 0.1244(16) Uani 1 1 d . . . . .
O3 O 0.7460(4) 0.0921(3) 0.6900(2) 0.1045(12) Uani 1 1 d . . . . .
O4 O 0.4250(2) 0.39308(18) 0.36036(19) 0.0552(7) Uani 1 1 d . . . . .
O5 O 0.5657(6) 0.3156(5) 0.8237(3) 0.171(3) Uani 1 1 d . . . . .
O6 O 0.3689(5) 0.3375(4) 0.8218(3) 0.1426(19) Uani 1 1 d . . . . .
C1 C 1.0097(4) 0.1150(3) -0.0522(3) 0.0658(12) Uani 1 1 d . . . . .
C2 C 0.8894(5) 0.1128(3) -0.0818(3) 0.0712(13) Uani 1 1 d . . . . .
H2 H 0.8711 0.1232 -0.1425 0.085 Uiso 1 1 calc R U . . .
C3 C 0.7923(4) 0.0947(3) -0.0197(3) 0.0630(11) Uani 1 1 d . . . . .
C4 C 0.6653(5) 0.1034(3) -0.0455(3) 0.0742(13) Uani 1 1 d . . . . .
H4 H 0.6454 0.1121 -0.1062 0.089 Uiso 1 1 calc R U . . .
C5 C 0.5720(4) 0.0993(3) 0.0159(4) 0.0700(13) Uani 1 1 d . . . . .
C6 C 0.6043(4) 0.0880(3) 0.1079(3) 0.0654(11) Uani 1 1 d . . . . .
C7 C 0.7268(4) 0.0766(3) 0.1348(3) 0.0589(11) Uani 1 1 d . . . . .
C8 C 0.8245(4) 0.0747(3) 0.0711(3) 0.0565(10) Uani 1 1 d . . . . .
C9 C 0.9559(4) 0.0619(3) 0.0902(3) 0.0595(11) Uani 1 1 d . . . . .
C10 C 1.1149(5) 0.1449(4) -0.1120(4) 0.0886(16) Uani 1 1 d . . . . .
H10A H 1.1581 0.1995 -0.0856 0.133 Uiso 1 1 calc R U . . .
H10B H 1.0827 0.1634 -0.1701 0.133 Uiso 1 1 calc R U . . .
H10C H 1.1716 0.0909 -0.1188 0.133 Uiso 1 1 calc R U . . .
C11 C 0.4370(4) 0.1106(4) -0.0119(4) 0.0945(18) Uani 1 1 d . . . . .
H11A H 0.4110 0.1771 -0.0021 0.142 Uiso 1 1 calc R U . . .
H11B H 0.3864 0.0672 0.0235 0.142 Uiso 1 1 calc R U . . .
H11C H 0.4280 0.0945 -0.0747 0.142 Uiso 1 1 calc R U . . .
C12 C 0.5132(5) 0.0924(4) 0.1773(4) 0.0829(15) Uani 1 1 d . . . . .
C13 C 0.9470(4) -0.0743(3) 0.1945(3) 0.0722(13) Uani 1 1 d . . . . .
H13A H 0.9903 -0.1226 0.1582 0.087 Uiso 1 1 calc R U . . .
H13B H 0.8590 -0.0778 0.1796 0.087 Uiso 1 1 calc R U . . .
C14 C 0.9653(4) -0.0979(4) 0.2933(3) 0.0814(14) Uani 1 1 d . . . . .
H14A H 0.9372 -0.1642 0.3052 0.098 Uiso 1 1 calc R U . . .
H14B H 0.9159 -0.0534 0.3297 0.098 Uiso 1 1 calc R U . . .
C15 C 1.1015(4) -0.0882(5) 0.3188(4) 0.0996(19) Uani 1 1 d . . . . .
H15A H 1.1115 -0.0981 0.3833 0.120 Uiso 1 1 calc R U . . .
H15B H 1.1496 -0.1381 0.2879 0.120 Uiso 1 1 calc R U . . .
C16 C 1.1487(4) 0.0114(5) 0.2935(3) 0.0867(16) Uani 1 1 d . . . . .
H16A H 1.2371 0.0154 0.3071 0.104 Uiso 1 1 calc R U . . .
H16B H 1.1063 0.0606 0.3294 0.104 Uiso 1 1 calc R U . . .
C17 C 1.1278(4) 0.0332(4) 0.1937(3) 0.0775(14) Uani 1 1 d . . . . .
H17A H 1.1559 0.0992 0.1800 0.093 Uiso 1 1 calc R U . . .
H17B H 1.1750 -0.0125 0.1572 0.093 Uiso 1 1 calc R U . . .
C18 C 0.7853(5) 0.1598(3) 0.2654(3) 0.0701(13) Uani 1 1 d . . . . .
H18A H 0.7232 0.2095 0.2522 0.084 Uiso 1 1 calc R U . . .
H18B H 0.8641 0.1811 0.2402 0.084 Uiso 1 1 calc R U . . .
C19 C 0.7981(4) 0.1473(3) 0.3656(3) 0.0582(11) Uani 1 1 d . . . . .
C20 C 0.8956(4) 0.1926(3) 0.4106(3) 0.0685(12) Uani 1 1 d . . . . .
H20 H 0.9531 0.2294 0.3782 0.082 Uiso 1 1 calc R U . . .
C21 C 0.9084(4) 0.1838(3) 0.5018(3) 0.0702(12) Uani 1 1 d . . . . .
H21 H 0.9739 0.2148 0.5317 0.084 Uiso 1 1 calc R U . . .
C22 C 0.8240(4) 0.1290(3) 0.5488(3) 0.0616(11) Uani 1 1 d . . . . .
C23 C 0.7266(4) 0.0827(3) 0.5068(3) 0.0662(11) Uani 1 1 d . . . . .
H23 H 0.6700 0.0457 0.5399 0.079 Uiso 1 1 calc R U . . .
C24 C 0.7138(4) 0.0920(3) 0.4149(3) 0.0642(11) Uani 1 1 d . . . . .
H24 H 0.6481 0.0609 0.3854 0.077 Uiso 1 1 calc R U . . .
C25 C 0.6877(4) 0.3666(3) 0.0786(3) 0.0615(11) Uani 1 1 d . . . . .
C26 C 0.5672(4) 0.3564(3) 0.0523(3) 0.0663(12) Uani 1 1 d . . . . .
H26 H 0.5487 0.3421 -0.0077 0.080 Uiso 1 1 calc R U . . .
C27 C 0.4705(4) 0.3673(3) 0.1146(3) 0.0594(11) Uani 1 1 d . . . . .
C28 C 0.3452(4) 0.3541(3) 0.0894(3) 0.0729(13) Uani 1 1 d . . . . .
H28 H 0.3263 0.3440 0.0288 0.087 Uiso 1 1 calc R U . . .
C29 C 0.2509(4) 0.3555(3) 0.1496(4) 0.0736(13) Uani 1 1 d . . . . .
C30 C 0.2841(4) 0.3677(3) 0.2417(3) 0.0644(12) Uani 1 1 d . . . . .
C31 C 0.4044(4) 0.3843(3) 0.2687(3) 0.0540(10) Uani 1 1 d . . . . .
C32 C 0.5014(4) 0.3903(3) 0.2049(3) 0.0515(10) Uani 1 1 d . . . . .
C33 C 0.6305(4) 0.4145(3) 0.2224(3) 0.0503(10) Uani 1 1 d . . . . .
C34 C 0.7955(4) 0.3508(4) 0.0166(3) 0.0823(15) Uani 1 1 d . . . . .
H34A H 0.8376 0.4120 0.0068 0.123 Uiso 1 1 calc R U . . .
H34B H 0.7658 0.3255 -0.0400 0.123 Uiso 1 1 calc R U . . .
H34C H 0.8524 0.3047 0.0433 0.123 Uiso 1 1 calc R U . . .
C35 C 0.1166(4) 0.3432(5) 0.1218(4) 0.107(2) Uani 1 1 d . . . . .
H35A H 0.0787 0.2929 0.1578 0.161 Uiso 1 1 calc R U . . .
H35B H 0.1124 0.3250 0.0593 0.161 Uiso 1 1 calc R U . . .
H35C H 0.0730 0.4039 0.1306 0.161 Uiso 1 1 calc R U . . .
C36 C 0.1913(5) 0.3628(4) 0.3122(4) 0.0824(16) Uani 1 1 d . . . . .
C37 C 0.6058(4) 0.5476(3) 0.3298(3) 0.0589(11) Uani 1 1 d . . . . .
H37A H 0.5174 0.5434 0.3165 0.071 Uiso 1 1 calc R U . . .
H37B H 0.6404 0.6009 0.2945 0.071 Uiso 1 1 calc R U . . .
C38 C 0.6249(4) 0.5679(3) 0.4289(3) 0.0699(12) Uani 1 1 d . . . . .
H38A H 0.5867 0.5160 0.4640 0.084 Uiso 1 1 calc R U . . .
H38B H 0.5846 0.6292 0.4446 0.084 Uiso 1 1 calc R U . . .
C39 C 0.7618(4) 0.5740(4) 0.4518(3) 0.0799(14) Uani 1 1 d . . . . .
H39A H 0.7725 0.5811 0.5166 0.096 Uiso 1 1 calc R U . . .
H39B H 0.7983 0.6309 0.4228 0.096 Uiso 1 1 calc R U . . .
C40 C 0.8268(4) 0.4817(4) 0.4200(3) 0.0719(13) Uani 1 1 d . . . . .
H40A H 0.9159 0.4888 0.4293 0.086 Uiso 1 1 calc R U . . .
H40B H 0.7987 0.4266 0.4560 0.086 Uiso 1 1 calc R U . . .
C41 C 0.8016(3) 0.4606(3) 0.3214(3) 0.0634(11) Uani 1 1 d . . . . .
H41A H 0.8375 0.5121 0.2846 0.076 Uiso 1 1 calc R U . . .
H41B H 0.8404 0.3990 0.3048 0.076 Uiso 1 1 calc R U . . .
C42 C 0.4778(5) 0.3063(3) 0.4006(3) 0.0740(13) Uani 1 1 d . . . . .
H42A H 0.5630 0.2977 0.3805 0.089 Uiso 1 1 calc R U . . .
H42B H 0.4302 0.2490 0.3826 0.089 Uiso 1 1 calc R U . . .
C43 C 0.4748(4) 0.3175(3) 0.5008(3) 0.0583(11) Uani 1 1 d . . . . .
C44 C 0.3650(4) 0.3354(3) 0.5460(3) 0.0695(12) Uani 1 1 d . . . . .
H44 H 0.2918 0.3448 0.5133 0.083 Uiso 1 1 calc R U . . .
C45 C 0.3624(4) 0.3397(4) 0.6387(3) 0.0766(14) Uani 1 1 d . . . . .
H45 H 0.2880 0.3514 0.6689 0.092 Uiso 1 1 calc R U . . .
C46 C 0.4706(5) 0.3267(3) 0.6855(3) 0.0695(12) Uani 1 1 d . . . . .
C47 C 0.5808(4) 0.3107(4) 0.6431(4) 0.0773(14) Uani 1 1 d . . . . .
H47 H 0.6540 0.3024 0.6761 0.093 Uiso 1 1 calc R U . . .
C48 C 0.5819(4) 0.3070(3) 0.5502(4) 0.0705(13) Uani 1 1 d . . . . .
H48 H 0.6570 0.2972 0.5205 0.085 Uiso 1 1 calc R U . . .
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'
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
C9 N1 C1 119.8(4) . . ?
C9 N2 C13 115.4(3) . . ?
C9 N2 C17 115.8(3) . . ?
C13 N2 C17 111.8(3) . . ?
O2 N4 O3 123.8(5) . . ?
O2 N4 C22 117.4(5) . . ?
O3 N4 C22 118.8(4) . . ?
C33 N5 C25 119.9(3) . . ?
C33 N6 C41 116.0(3) . . ?
C33 N6 C37 115.9(3) . . ?
C41 N6 C37 110.8(3) . . ?
O5 N8 O6 124.0(6) . . ?
O5 N8 C46 117.4(6) . . ?
O6 N8 C46 118.6(6) . . ?
C7 O1 C18 112.5(3) . . ?
C31 O4 C42 113.4(3) . . ?
N1 C1 C2 122.2(4) . . ?
N1 C1 C10 115.5(4) . . ?
C2 C1 C10 122.2(4) . . ?
C1 C2 C3 119.6(4) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C8 C3 C2 118.4(4) . . ?
C8 C3 C4 120.2(4) . . ?
C2 C3 C4 121.3(4) . . ?
C5 C4 C3 121.8(4) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C4 C5 C6 118.2(4) . . ?
C4 C5 C11 121.5(5) . . ?
C6 C5 C11 120.3(5) . . ?
C7 C6 C5 121.3(4) . . ?
C7 C6 C12 116.9(5) . . ?
C5 C6 C12 121.7(4) . . ?
O1 C7 C6 117.0(4) . . ?
O1 C7 C8 121.9(4) . . ?
C6 C7 C8 121.1(4) . . ?
C3 C8 C7 116.9(4) . . ?
C3 C8 C9 116.3(4) . . ?
C7 C8 C9 126.6(4) . . ?
N1 C9 N2 117.8(4) . . ?
N1 C9 C8 122.1(4) . . ?
N2 C9 C8 120.1(4) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C6 177.4(6) . . ?
N2 C13 C14 111.1(4) . . ?
N2 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
N2 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 110.1(4) . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C16 C15 C14 110.1(4) . . ?
C16 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.2 . . ?
C15 C16 C17 111.8(5) . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
N2 C17 C16 108.9(4) . . ?
N2 C17 H17A 109.9 . . ?
C16 C17 H17A 109.9 . . ?
N2 C17 H17B 109.9 . . ?
C16 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
O1 C18 C19 109.4(3) . . ?
O1 C18 H18A 109.8 . . ?
C19 C18 H18A 109.8 . . ?
O1 C18 H18B 109.8 . . ?
C19 C18 H18B 109.8 . . ?
H18A C18 H18B 108.2 . . ?
C20 C19 C24 118.9(4) . . ?
C20 C19 C18 119.4(4) . . ?
C24 C19 C18 121.7(4) . . ?
C21 C20 C19 120.8(4) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 119.2(4) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C21 C22 C23 121.8(4) . . ?
C21 C22 N4 119.5(4) . . ?
C23 C22 N4 118.7(4) . . ?
C22 C23 C24 118.7(4) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C23 C24 C19 120.6(4) . . ?
C23 C24 H24 119.7 . . ?
C19 C24 H24 119.7 . . ?
C26 C25 N5 121.5(4) . . ?
C26 C25 C34 123.2(4) . . ?
N5 C25 C34 115.1(4) . . ?
C25 C26 C27 120.6(4) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C26 C27 C28 121.5(4) . . ?
C26 C27 C32 118.5(4) . . ?
C28 C27 C32 120.0(4) . . ?
C29 C28 C27 122.7(5) . . ?
C29 C28 H28 118.6 . . ?
C27 C28 H28 118.6 . . ?
C28 C29 C30 116.8(4) . . ?
C28 C29 C35 122.4(5) . . ?
C30 C29 C35 120.8(5) . . ?
C31 C30 C29 122.2(4) . . ?
C31 C30 C36 116.6(4) . . ?
C29 C30 C36 121.2(4) . . ?
C30 C31 O4 116.6(4) . . ?
C30 C31 C32 120.8(4) . . ?
O4 C31 C32 122.6(3) . . ?
C31 C32 C27 116.8(4) . . ?
C31 C32 C33 127.0(4) . . ?
C27 C32 C33 116.2(4) . . ?
N5 C33 N6 117.1(3) . . ?
N5 C33 C32 122.1(4) . . ?
N6 C33 C32 120.8(4) . . ?
C25 C34 H34A 109.5 . . ?
C25 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C25 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C29 C35 H35A 109.5 . . ?
C29 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C29 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N7 C36 C30 179.4(6) . . ?
N6 C37 C38 110.1(3) . . ?
N6 C37 H37A 109.6 . . ?
C38 C37 H37A 109.6 . . ?
N6 C37 H37B 109.6 . . ?
C38 C37 H37B 109.6 . . ?
H37A C37 H37B 108.2 . . ?
C37 C38 C39 110.9(4) . . ?
C37 C38 H38A 109.4 . . ?
C39 C38 H38A 109.4 . . ?
C37 C38 H38B 109.4 . . ?
C39 C38 H38B 109.4 . . ?
H38A C38 H38B 108.0 . . ?
C38 C39 C40 109.4(4) . . ?
C38 C39 H39A 109.8 . . ?
C40 C39 H39A 109.8 . . ?
C38 C39 H39B 109.8 . . ?
C40 C39 H39B 109.8 . . ?
H39A C39 H39B 108.2 . . ?
C41 C40 C39 112.2(4) . . ?
C41 C40 H40A 109.2 . . ?
C39 C40 H40A 109.2 . . ?
C41 C40 H40B 109.2 . . ?
C39 C40 H40B 109.2 . . ?
H40A C40 H40B 107.9 . . ?
N6 C41 C40 110.1(3) . . ?
N6 C41 H41A 109.6 . . ?
C40 C41 H41A 109.6 . . ?
N6 C41 H41B 109.6 . . ?
C40 C41 H41B 109.6 . . ?
H41A C41 H41B 108.2 . . ?
O4 C42 C43 108.5(3) . . ?
O4 C42 H42A 110.0 . . ?
C43 C42 H42A 110.0 . . ?
O4 C42 H42B 110.0 . . ?
C43 C42 H42B 110.0 . . ?
H42A C42 H42B 108.4 . . ?
C48 C43 C44 118.5(4) . . ?
C48 C43 C42 120.0(4) . . ?
C44 C43 C42 121.6(4) . . ?
C45 C44 C43 121.0(4) . . ?
C45 C44 H44 119.5 . . ?
C43 C44 H44 119.5 . . ?
C46 C45 C44 118.7(4) . . ?
C46 C45 H45 120.6 . . ?
C44 C45 H45 120.6 . . ?
C47 C46 C45 121.9(5) . . ?
C47 C46 N8 118.9(5) . . ?
C45 C46 N8 119.2(5) . . ?
C46 C47 C48 118.6(5) . . ?
C46 C47 H47 120.7 . . ?
C48 C47 H47 120.7 . . ?
C43 C48 C47 121.3(4) . . ?
C43 C48 H48 119.3 . . ?
C47 C48 H48 119.3 . . ?
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 C9 1.314(5) . ?
N1 C1 1.352(5) . ?
N2 C9 1.393(5) . ?
N2 C13 1.467(5) . ?
N2 C17 1.469(5) . ?
N3 C12 1.140(7) . ?
N4 O2 1.220(5) . ?
N4 O3 1.221(5) . ?
N4 C22 1.460(6) . ?
N5 C33 1.312(5) . ?
N5 C25 1.360(5) . ?
N6 C33 1.395(5) . ?
N6 C41 1.466(5) . ?
N6 C37 1.469(5) . ?
N7 C36 1.139(6) . ?
N8 O5 1.206(6) . ?
N8 O6 1.210(6) . ?
N8 C46 1.467(6) . ?
O1 C7 1.370(5) . ?
O1 C18 1.428(5) . ?
O4 C31 1.381(5) . ?
O4 C42 1.440(5) . ?
C1 C2 1.362(6) . ?
C1 C10 1.495(6) . ?
C2 C3 1.414(6) . ?
C2 H2 0.9300 . ?
C3 C8 1.414(5) . ?
C3 C4 1.419(6) . ?
C4 C5 1.357(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.414(6) . ?
C5 C11 1.511(5) . ?
C6 C7 1.381(5) . ?
C6 C12 1.422(7) . ?
C7 C8 1.414(6) . ?
C8 C9 1.448(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.510(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.514(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.498(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.523(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.500(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.383(6) . ?
C19 C24 1.388(5) . ?
C20 C21 1.363(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.368(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.368(6) . ?
C23 C24 1.374(6) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.356(6) . ?
C25 C34 1.496(6) . ?
C26 C27 1.400(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.405(6) . ?
C27 C32 1.413(5) . ?
C28 C29 1.352(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.418(6) . ?
C29 C35 1.507(6) . ?
C30 C31 1.368(5) . ?
C30 C36 1.449(7) . ?
C31 C32 1.411(5) . ?
C32 C33 1.446(5) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C37 C38 1.507(6) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 C39 1.509(6) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 C40 1.515(7) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 C41 1.512(6) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 C43 1.493(6) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C43 C48 1.367(6) . ?
C43 C44 1.379(5) . ?
C44 C45 1.375(6) . ?
C44 H44 0.9300 . ?
C45 C46 1.361(6) . ?
C45 H45 0.9300 . ?
C46 C47 1.359(6) . ?
C47 C48 1.377(6) . ?
C47 H47 0.9300 . ?
C48 H48 0.9300 . ?
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
C9 N1 C1 C2 -4.6(7) . . . . ?
C9 N1 C1 C10 177.9(4) . . . . ?
N1 C1 C2 C3 9.8(7) . . . . ?
C10 C1 C2 C3 -172.9(4) . . . . ?
C1 C2 C3 C8 -2.9(6) . . . . ?
C1 C2 C3 C4 172.4(4) . . . . ?
C8 C3 C4 C5 4.3(7) . . . . ?
C2 C3 C4 C5 -170.9(4) . . . . ?
C3 C4 C5 C6 1.3(7) . . . . ?
C3 C4 C5 C11 178.9(4) . . . . ?
C4 C5 C6 C7 -3.1(6) . . . . ?
C11 C5 C6 C7 179.3(4) . . . . ?
C4 C5 C6 C12 174.0(5) . . . . ?
C11 C5 C6 C12 -3.6(7) . . . . ?
C18 O1 C7 C6 -97.3(4) . . . . ?
C18 O1 C7 C8 81.8(5) . . . . ?
C5 C6 C7 O1 178.4(4) . . . . ?
C12 C6 C7 O1 1.2(6) . . . . ?
C5 C6 C7 C8 -0.7(6) . . . . ?
C12 C6 C7 C8 -177.9(4) . . . . ?
C2 C3 C8 C7 167.5(4) . . . . ?
C4 C3 C8 C7 -7.9(6) . . . . ?
C2 C3 C8 C9 -7.8(6) . . . . ?
C4 C3 C8 C9 176.8(4) . . . . ?
O1 C7 C8 C3 -172.9(4) . . . . ?
C6 C7 C8 C3 6.2(6) . . . . ?
O1 C7 C8 C9 1.8(6) . . . . ?
C6 C7 C8 C9 -179.1(4) . . . . ?
C1 N1 C9 N2 173.8(4) . . . . ?
C1 N1 C9 C8 -7.2(6) . . . . ?
C13 N2 C9 N1 -121.8(4) . . . . ?
C17 N2 C9 N1 11.5(6) . . . . ?
C13 N2 C9 C8 59.2(5) . . . . ?
C17 N2 C9 C8 -167.4(4) . . . . ?
C3 C8 C9 N1 13.3(6) . . . . ?
C7 C8 C9 N1 -161.5(4) . . . . ?
C3 C8 C9 N2 -167.8(4) . . . . ?
C7 C8 C9 N2 17.5(6) . . . . ?
C9 N2 C13 C14 -165.4(4) . . . . ?
C17 N2 C13 C14 59.5(5) . . . . ?
N2 C13 C14 C15 -56.5(5) . . . . ?
C13 C14 C15 C16 54.5(6) . . . . ?
C14 C15 C16 C17 -55.8(6) . . . . ?
C9 N2 C17 C16 166.6(4) . . . . ?
C13 N2 C17 C16 -58.5(5) . . . . ?
C15 C16 C17 N2 57.1(6) . . . . ?
C7 O1 C18 C19 175.5(3) . . . . ?
O1 C18 C19 C20 139.8(4) . . . . ?
O1 C18 C19 C24 -40.7(5) . . . . ?
C24 C19 C20 C21 -0.6(6) . . . . ?
C18 C19 C20 C21 178.9(4) . . . . ?
C19 C20 C21 C22 0.5(7) . . . . ?
C20 C21 C22 C23 -0.2(6) . . . . ?
C20 C21 C22 N4 -178.4(4) . . . . ?
O2 N4 C22 C21 -15.5(6) . . . . ?
O3 N4 C22 C21 163.5(4) . . . . ?
O2 N4 C22 C23 166.2(4) . . . . ?
O3 N4 C22 C23 -14.8(6) . . . . ?
C21 C22 C23 C24 0.0(6) . . . . ?
N4 C22 C23 C24 178.2(4) . . . . ?
C22 C23 C24 C19 -0.1(6) . . . . ?
C20 C19 C24 C23 0.4(6) . . . . ?
C18 C19 C24 C23 -179.1(4) . . . . ?
C33 N5 C25 C26 4.5(6) . . . . ?
C33 N5 C25 C34 -179.7(4) . . . . ?
N5 C25 C26 C27 -7.9(6) . . . . ?
C34 C25 C26 C27 176.7(4) . . . . ?
C25 C26 C27 C28 -178.0(4) . . . . ?
C25 C26 C27 C32 0.9(6) . . . . ?
C26 C27 C28 C29 174.0(4) . . . . ?
C32 C27 C28 C29 -4.9(6) . . . . ?
C27 C28 C29 C30 -2.1(7) . . . . ?
C27 C28 C29 C35 178.8(4) . . . . ?
C28 C29 C30 C31 4.5(6) . . . . ?
C35 C29 C30 C31 -176.4(4) . . . . ?
C28 C29 C30 C36 -175.3(4) . . . . ?
C35 C29 C30 C36 3.8(7) . . . . ?
C29 C30 C31 O4 -178.8(3) . . . . ?
C36 C30 C31 O4 1.0(5) . . . . ?
C29 C30 C31 C32 0.3(6) . . . . ?
C36 C30 C31 C32 -179.9(4) . . . . ?
C42 O4 C31 C30 102.4(4) . . . . ?
C42 O4 C31 C32 -76.6(4) . . . . ?
C30 C31 C32 C27 -7.2(5) . . . . ?
O4 C31 C32 C27 171.9(3) . . . . ?
C30 C31 C32 C33 175.1(4) . . . . ?
O4 C31 C32 C33 -5.9(6) . . . . ?
C26 C27 C32 C31 -169.5(4) . . . . ?
C28 C27 C32 C31 9.4(5) . . . . ?
C26 C27 C32 C33 8.5(5) . . . . ?
C28 C27 C32 C33 -172.6(4) . . . . ?
C25 N5 C33 N6 -174.8(3) . . . . ?
C25 N5 C33 C32 5.8(6) . . . . ?
C41 N6 C33 N5 -9.8(5) . . . . ?
C37 N6 C33 N5 122.8(4) . . . . ?
C41 N6 C33 C32 169.7(3) . . . . ?
C37 N6 C33 C32 -57.8(5) . . . . ?
C31 C32 C33 N5 165.6(4) . . . . ?
C27 C32 C33 N5 -12.2(5) . . . . ?
C31 C32 C33 N6 -13.8(6) . . . . ?
C27 C32 C33 N6 168.4(3) . . . . ?
C33 N6 C37 C38 163.9(3) . . . . ?
C41 N6 C37 C38 -61.1(4) . . . . ?
N6 C37 C38 C39 58.8(5) . . . . ?
C37 C38 C39 C40 -54.3(5) . . . . ?
C38 C39 C40 C41 53.1(5) . . . . ?
C33 N6 C41 C40 -166.0(3) . . . . ?
C37 N6 C41 C40 59.2(4) . . . . ?
C39 C40 C41 N6 -55.7(5) . . . . ?
C31 O4 C42 C43 -170.1(3) . . . . ?
O4 C42 C43 C48 -125.5(4) . . . . ?
O4 C42 C43 C44 56.5(5) . . . . ?
C48 C43 C44 C45 -2.0(6) . . . . ?
C42 C43 C44 C45 176.0(4) . . . . ?
C43 C44 C45 C46 0.5(7) . . . . ?
C44 C45 C46 C47 0.8(7) . . . . ?
C44 C45 C46 N8 -177.6(4) . . . . ?
O5 N8 C46 C47 1.7(8) . . . . ?
O6 N8 C46 C47 -177.1(5) . . . . ?
O5 N8 C46 C45 -179.9(6) . . . . ?
O6 N8 C46 C45 1.3(8) . . . . ?
C45 C46 C47 C48 -0.5(7) . . . . ?
N8 C46 C47 C48 177.9(4) . . . . ?
C44 C43 C48 C47 2.2(6) . . . . ?
C42 C43 C48 C47 -175.8(4) . . . . ?
C46 C47 C48 C43 -1.1(7) . . . . ?
