#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/67/7236706.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_7236706
loop_
_publ_author_name
'Li, Xiangchun'
'Wang, Hengbin'
'Schneider, Julia A.'
'Wei, Zitang'
'Lai, Wen-Yong'
'Huang, Wei'
'Wudl, Fred'
'Zheng, Yonghao'
_publ_section_title
;
 Catalyst-free one-step synthesis of ortho-tetraaryl perylene diimides for
 efficient OPV non-fullerene acceptors
;
_journal_issue                   11
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              2781
_journal_paper_doi               10.1039/C7TC00263G
_journal_volume                  5
_journal_year                    2017
_chemical_formula_sum            'C83 H96 Cl2 N2 O4'
_chemical_formula_weight         1256.51
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-09-13 deposited with the CCDC.
2017-02-15 downloaded from the CCDC.
;
_cell_angle_alpha                91.262(13)
_cell_angle_beta                 104.023(12)
_cell_angle_gamma                104.588(10)
_cell_formula_units_Z            2
_cell_length_a                   12.158(6)
_cell_length_b                   14.546(7)
_cell_length_c                   20.965(10)
_cell_measurement_reflns_used    448
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      18.7
_cell_measurement_theta_min      1.5
_cell_volume                     3468(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  'BruKer Kappa Apex II'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1082
_diffrn_reflns_av_unetI/netI     0.3269
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17076
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        24.674
_diffrn_reflns_theta_max         24.674
_diffrn_reflns_theta_min         1.005
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.5457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_description       needle
_exptl_crystal_F_000             1348
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.869
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     837
_refine_ls_number_reflns         11121
_refine_ls_number_restraints     85
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.3513
_refine_ls_R_factor_gt           0.1430
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²+0.5831P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3379
_refine_ls_wR_factor_ref         0.4471
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3285
_reflns_number_total             11121
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7tc00263g2.cif
_cod_data_source_block           07282016_0m_a
_cod_database_code               7236706
_shelx_shelxl_version_number     2014/7
_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   0.957
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
C1 C 0.2947(9) 0.3765(8) 0.1780(5) 0.045(3) Uani 1 1 d . .
C2 C 0.1918(8) 0.3903(8) 0.1275(5) 0.040(3) Uani 1 1 d . .
C3 C 0.0874(8) 0.3136(7) 0.1071(5) 0.035(3) Uani 1 1 d . .
C4 C -0.0042(8) 0.3265(7) 0.0593(5) 0.035(3) Uani 1 1 d . .
H4 H -0.0726 0.2746 0.0453 0.042 Uiso 1 1 calc R U
C5 C -0.0035(8) 0.4108(7) 0.0296(5) 0.032(3) Uani 1 1 d . .
C6 C 0.0981(8) 0.4871(7) 0.0497(5) 0.025(2) Uani 1 1 d . .
C7 C 0.1031(8) 0.5759(7) 0.0207(5) 0.032(3) Uani 1 1 d . .
C8 C 0.2067(8) 0.6474(7) 0.0422(5) 0.040(3) Uani 1 1 d . .
H8 H 0.2141 0.7047 0.0209 0.048 Uiso 1 1 calc R U
C9 C 0.3015(8) 0.6400(7) 0.0939(5) 0.035(3) Uani 1 1 d . .
C10 C 0.2972(8) 0.5556(7) 0.1219(5) 0.033(3) Uani 1 1 d . .
C11 C 0.3952(9) 0.5453(8) 0.1778(5) 0.043(3) Uani 1 1 d . .
C12 C 0.1959(8) 0.4777(7) 0.0995(5) 0.030(3) Uani 1 1 d . .
C13 C 0.0721(8) 0.2175(9) 0.1347(6) 0.042(3) Uani 1 1 d . .
C14 C 0.0808(9) 0.1409(9) 0.0972(6) 0.053(3) Uani 1 1 d . .
C15 C 0.0534(10) 0.0497(9) 0.1187(7) 0.061(4) Uani 1 1 d . .
H15 H 0.0591 -0.0026 0.0930 0.073 Uiso 1 1 calc R U
C16 C 0.0189(10) 0.0334(10) 0.1751(8) 0.066(4) Uani 1 1 d . .
C17 C 0.0117(10) 0.1095(10) 0.2110(7) 0.067(4) Uani 1 1 d . .
H17 H -0.0113 0.0983 0.2510 0.080 Uiso 1 1 calc R U
C18 C 0.0358(10) 0.2031(9) 0.1931(7) 0.054(3) Uani 1 1 d . .
C19 C 0.1242(12) 0.1552(9) 0.0352(6) 0.072(4) Uani 1 1 d . .
H19A H 0.0722 0.1839 0.0035 0.108 Uiso 1 1 calc R U
H19B H 0.1243 0.0934 0.0157 0.108 Uiso 1 1 calc R U
H19C H 0.2042 0.1974 0.0464 0.108 Uiso 1 1 calc R U
C20 C -0.0095(11) -0.0664(9) 0.1954(7) 0.100(6) Uani 1 1 d . .
H20A H -0.0334 -0.0662 0.2368 0.151 Uiso 1 1 calc R U
H20B H 0.0601 -0.0909 0.2017 0.151 Uiso 1 1 calc R U
H20C H -0.0738 -0.1073 0.1609 0.151 Uiso 1 1 calc R U
C21 C 0.0307(10) 0.2841(10) 0.2333(6) 0.064(4) Uani 1 1 d . .
H21A H -0.0135 0.2612 0.2658 0.096 Uiso 1 1 calc R U
H21B H -0.0084 0.3252 0.2049 0.096 Uiso 1 1 calc R U
H21C H 0.1107 0.3205 0.2563 0.096 Uiso 1 1 calc R U
C22 C 0.4056(9) 0.7281(8) 0.1110(6) 0.046(3) Uani 1 1 d . .
C23 C 0.4023(10) 0.8019(8) 0.1529(7) 0.061(4) Uani 1 1 d . .
C24 C 0.4972(11) 0.8816(8) 0.1664(7) 0.074(4) Uani 1 1 d . .
H24 H 0.4973 0.9329 0.1953 0.089 Uiso 1 1 calc R U
C25 C 0.5899(10) 0.8897(11) 0.1401(8) 0.081(5) Uani 1 1 d . .
C26 C 0.5867(10) 0.8160(10) 0.0972(7) 0.074(4) Uani 1 1 d . .
H26 H 0.6491 0.8223 0.0764 0.089 Uiso 1 1 calc R U
C27 C 0.4962(10) 0.7326(8) 0.0829(6) 0.051(3) Uani 1 1 d . .
C28 C 0.3011(12) 0.7936(11) 0.1829(7) 0.094(5) Uani 1 1 d . .
H28A H 0.2968 0.7408 0.2112 0.141 Uiso 1 1 calc R U
H28B H 0.2280 0.7814 0.1478 0.141 Uiso 1 1 calc R U
H28C H 0.3120 0.8531 0.2093 0.141 Uiso 1 1 calc R U
C29 C 0.6922(11) 0.9806(10) 0.1599(9) 0.122(7) Uani 1 1 d . .
H29A H 0.7446 0.9746 0.2023 0.182 Uiso 1 1 calc R U
H29B H 0.6611 1.0358 0.1640 0.182 Uiso 1 1 calc R U
H29C H 0.7362 0.9895 0.1260 0.182 Uiso 1 1 calc R U
C30 C 0.5021(11) 0.6521(10) 0.0408(6) 0.080(5) Uani 1 1 d . .
H30A H 0.5412 0.6102 0.0685 0.120 Uiso 1 1 calc R U
H30B H 0.5468 0.6767 0.0089 0.120 Uiso 1 1 calc R U
H30C H 0.4223 0.6161 0.0172 0.120 Uiso 1 1 calc R U
C31 C 0.6914(15) 0.2562(10) 0.1176(9) 0.126(7) Uani 1 1 d . .
H31A H 0.7261 0.2276 0.1567 0.190 Uiso 1 1 calc R U
H31B H 0.7068 0.2292 0.0785 0.190 Uiso 1 1 calc R U
H31C H 0.6063 0.2429 0.1120 0.190 Uiso 1 1 calc R U
C32 C 0.7454(13) 0.3635(11) 0.1263(8) 0.093(5) Uani 1 1 d . .
H32A H 0.8300 0.3773 0.1278 0.111 Uiso 1 1 calc R U
H32B H 0.7067 0.3931 0.0882 0.111 Uiso 1 1 calc R U
C33 C 0.7319(12) 0.4027(10) 0.1848(8) 0.080(4) Uani 1 1 d . .
H33A H 0.7818 0.4691 0.1942 0.097 Uiso 1 1 calc R U
H33B H 0.7610 0.3662 0.2216 0.097 Uiso 1 1 calc R U
C34 C 0.6024(9) 0.4029(9) 0.1835(7) 0.069(4) Uani 1 1 d . .
H34A H 0.5688 0.4324 0.1439 0.083 Uiso 1 1 calc R U
H34B H 0.5538 0.3364 0.1808 0.083 Uiso 1 1 calc R U
C35 C 0.5987(10) 0.4563(10) 0.2433(6) 0.066(4) Uani 1 1 d . .
H35A H 0.6304 0.5250 0.2392 0.080 Uiso 1 1 calc R U
H35B H 0.6530 0.4389 0.2815 0.080 Uiso 1 1 calc R U
C36 C 0.4839(9) 0.4438(9) 0.2591(6) 0.055(4) Uani 1 1 d . .
H36 H 0.4597 0.3746 0.2662 0.066 Uiso 1 1 calc R U
C37 C 0.4825(10) 0.4939(11) 0.3222(5) 0.072(4) Uani 1 1 d . .
H37A H 0.5430 0.4788 0.3582 0.086 Uiso 1 1 calc R U
H37B H 0.5075 0.5634 0.3184 0.086 Uiso 1 1 calc R U
C38 C 0.3717(12) 0.4735(11) 0.3426(6) 0.083(5) Uani 1 1 d . .
H38A H 0.3432 0.4040 0.3449 0.100 Uiso 1 1 calc R U
H38B H 0.3115 0.4934 0.3091 0.100 Uiso 1 1 calc R U
C39 C 0.3866(13) 0.5244(11) 0.4085(6) 0.080(5) Uani 1 1 d . .
H39A H 0.4143 0.5939 0.4060 0.096 Uiso 1 1 calc R U
H39B H 0.4475 0.5050 0.4419 0.096 Uiso 1 1 calc R U
C40 C 0.2687(13) 0.5020(14) 0.4313(8) 0.109(6) Uani 1 1 d . .
H40A H 0.2768 0.5505 0.4673 0.130 Uiso 1 1 calc R U
H40B H 0.2041 0.5081 0.3939 0.130 Uiso 1 1 calc R U
C41 C 0.2369(15) 0.4095(11) 0.4540(11) 0.135(8) Uani 1 1 d . .
H41A H 0.2081 0.3612 0.4162 0.202 Uiso 1 1 calc R U
H41B H 0.1751 0.4063 0.4770 0.202 Uiso 1 1 calc R U
H41C H 0.3060 0.3973 0.4843 0.202 Uiso 1 1 calc R U
C42 C 0.7233(11) 0.1692(8) 0.5132(6) 0.057(4) Uani 1 1 d . .
C43 C 0.7801(9) 0.2655(7) 0.4914(5) 0.040(3) Uani 1 1 d . .
C44 C 0.7424(8) 0.2900(7) 0.4296(5) 0.042(3) Uani 1 1 d . .
C45 C 0.8059(9) 0.3753(7) 0.4124(5) 0.035(3) Uani 1 1 d . .
H45 H 0.7796 0.3926 0.3691 0.042 Uiso 1 1 calc R U
C46 C 0.9033(8) 0.4359(7) 0.4534(5) 0.037(3) Uani 1 1 d . .
C47 C 0.9370(9) 0.4131(7) 0.5206(5) 0.033(3) Uani 1 1 d . .
C48 C 1.0315(8) 0.4747(7) 0.5668(5) 0.039(3) Uani 1 1 d . .
C49 C 1.0584(8) 0.4531(7) 0.6308(5) 0.035(3) Uani 1 1 d . .
H49 H 1.1204 0.4965 0.6623 0.042 Uiso 1 1 calc R U
C50 C 0.9958(9) 0.3672(7) 0.6517(5) 0.038(3) Uani 1 1 d . .
C51 C 0.9065(8) 0.3052(7) 0.6063(6) 0.040(3) Uani 1 1 d . .
C52 C 0.8409(10) 0.2177(8) 0.6272(6) 0.051(3) Uani 1 1 d . .
C53 C 0.8752(8) 0.3286(7) 0.5402(5) 0.037(3) Uani 1 1 d . .
C54 C 0.6376(9) 0.2348(8) 0.3762(6) 0.047(3) Uani 1 1 d . .
C55 C 0.5246(9) 0.2398(8) 0.3783(6) 0.043(3) Uani 1 1 d . .
C56 C 0.4325(9) 0.1941(7) 0.3249(6) 0.052(3) Uani 1 1 d . .
H56 H 0.3553 0.1959 0.3257 0.062 Uiso 1 1 calc R U
C57 C 0.4455(9) 0.1471(7) 0.2715(6) 0.042(3) Uani 1 1 d . .
C58 C 0.5587(10) 0.1435(8) 0.2710(6) 0.056(3) Uani 1 1 d . .
H58 H 0.5704 0.1097 0.2349 0.067 Uiso 1 1 calc R U
C59 C 0.6559(9) 0.1891(8) 0.3231(6) 0.047(3) Uani 1 1 d . .
C60 C 0.5028(10) 0.2834(9) 0.4350(6) 0.063(4) Uani 1 1 d . .
H60A H 0.5293 0.2512 0.4742 0.094 Uiso 1 1 calc R U
H60B H 0.4185 0.2775 0.4273 0.094 Uiso 1 1 calc R U
H60C H 0.5460 0.3510 0.4421 0.094 Uiso 1 1 calc R U
C61 C 0.3433(10) 0.0960(8) 0.2178(6) 0.071(4) Uani 1 1 d . .
H61A H 0.3698 0.0835 0.1787 0.107 Uiso 1 1 calc R U
H61B H 0.2877 0.1353 0.2069 0.107 Uiso 1 1 calc R U
H61C H 0.3045 0.0355 0.2322 0.107 Uiso 1 1 calc R U
C62 C 0.7752(10) 0.1812(10) 0.3200(6) 0.077(4) Uani 1 1 d . .
H62A H 0.8282 0.2452 0.3234 0.115 Uiso 1 1 calc R U
H62B H 0.7689 0.1468 0.2780 0.115 Uiso 1 1 calc R U
H62C H 0.8063 0.1465 0.3566 0.115 Uiso 1 1 calc R U
C63 C 1.0381(9) 0.3589(7) 0.7238(5) 0.036(3) Uani 1 1 d . .
C64 C 0.9849(9) 0.3879(7) 0.7680(6) 0.041(3) Uani 1 1 d . .
C65 C 1.0328(10) 0.3846(8) 0.8350(6) 0.053(3) Uani 1 1 d . .
H65 H 0.9959 0.4054 0.8656 0.064 Uiso 1 1 calc R U
C66 C 1.1314(9) 0.3527(8) 0.8593(6) 0.046(3) Uani 1 1 d . .
C67 C 1.1834(10) 0.3215(8) 0.8135(6) 0.052(3) Uani 1 1 d . .
H67 H 1.2510 0.2987 0.8287 0.062 Uiso 1 1 calc R U
C68 C 1.1376(10) 0.3233(8) 0.7449(6) 0.046(3) Uani 1 1 d . .
C69 C 0.8782(10) 0.4242(9) 0.7464(6) 0.060(4) Uani 1 1 d . .
H69A H 0.8989 0.4843 0.7264 0.090 Uiso 1 1 calc R U
H69B H 0.8486 0.4349 0.7846 0.090 Uiso 1 1 calc R U
H69C H 0.8174 0.3771 0.7139 0.090 Uiso 1 1 calc R U
C70 C 1.1826(11) 0.3523(9) 0.9307(5) 0.061(4) Uani 1 1 d . .
H70A H 1.2303 0.4166 0.9488 0.092 Uiso 1 1 calc R U
H70B H 1.2321 0.3079 0.9378 0.092 Uiso 1 1 calc R U
H70C H 1.1192 0.3323 0.9528 0.092 Uiso 1 1 calc R U
C71 C 1.1950(10) 0.2835(10) 0.6975(6) 0.066(4) Uani 1 1 d . .
H71A H 1.1354 0.2343 0.6660 0.099 Uiso 1 1 calc R U
H71B H 1.2559 0.2556 0.7225 0.099 Uiso 1 1 calc R U
H71C H 1.2306 0.3351 0.6736 0.099 Uiso 1 1 calc R U
C72 C 0.258(4) 0.0798(18) 0.680(2) 0.45(4) Uani 1 1 d D .
H72A H 0.2104 0.0152 0.6821 0.673 Uiso 1 1 calc R U
H72B H 0.2077 0.1170 0.6553 0.673 Uiso 1 1 calc R U
H72C H 0.2945 0.1106 0.7249 0.673 Uiso 1 1 calc R U
C73 C 0.3447(17) 0.0752(13) 0.6488(13) 0.206(13) Uani 1 1 d D .
H73A H 0.3035 0.0318 0.6084 0.247 Uiso 1 1 calc R U
H73B H 0.3946 0.0405 0.6777 0.247 Uiso 1 1 calc R U
C74 C 0.4231(16) 0.1492(12) 0.6290(13) 0.32(3) Uani 1 1 d D .
H74A H 0.4372 0.2048 0.6608 0.384 Uiso 1 1 calc R U
H74B H 0.3788 0.1647 0.5862 0.384 Uiso 1 1 calc R U
C75 C 0.5336(10) 0.1492(10) 0.6204(8) 0.100(6) Uani 1 1 d D .
H75A H 0.5452 0.1918 0.5851 0.120 Uiso 1 1 calc R U
H75B H 0.5906 0.1828 0.6614 0.120 Uiso 1 1 calc R U
C76 C 0.5734(12) 0.0723(9) 0.6062(10) 0.139(8) Uani 1 1 d D .
H76A H 0.5179 0.0411 0.5641 0.167 Uiso 1 1 calc R U
H76B H 0.5565 0.0284 0.6401 0.167 Uiso 1 1 calc R U
C77 C 0.6817(9) 0.0665(7) 0.5997(7) 0.071(4) Uani 1 1 d D .
H77 H 0.7234 0.0767 0.6477 0.086 Uiso 1 1 calc R U
C78 C 0.7156(13) -0.0138(8) 0.5849(10) 0.156(9) Uani 1 1 d D .
H78A H 0.6731 -0.0647 0.6074 0.187 Uiso 1 1 calc R U
H78B H 0.6791 -0.0307 0.5371 0.187 Uiso 1 1 calc R U
C79 C 0.8262(13) -0.0276(11) 0.5946(12) 0.194(13) Uani 1 1 d D .
H79A H 0.8602 -0.0171 0.6430 0.233 Uiso 1 1 calc R U
H79B H 0.8713 0.0266 0.5757 0.233 Uiso 1 1 calc R U
C80 C 0.8582(18) -0.1072(11) 0.5747(12) 0.213(14) Uani 1 1 d D .
H80A H 0.8717 -0.1428 0.6143 0.255 Uiso 1 1 calc R U
H80B H 0.7867 -0.1474 0.5433 0.255 Uiso 1 1 calc R U
C81 C 0.9497(17) -0.1079(16) 0.5465(15) 0.36(3) Uani 1 1 d D .
H81A H 1.0194 -0.1025 0.5838 0.428 Uiso 1 1 calc R U
H81B H 0.9649 -0.0475 0.5253 0.428 Uiso 1 1 calc R U
C82 C 0.953(2) -0.1794(15) 0.5002(12) 0.224(14) Uani 1 1 d D .
H82A H 1.0025 -0.1505 0.4717 0.336 Uiso 1 1 calc R U
H82B H 0.8727 -0.2088 0.4732 0.336 Uiso 1 1 calc R U
H82C H 0.9846 -0.2282 0.5237 0.336 Uiso 1 1 calc R U
C83 C 0.6570(17) 0.0491(14) 0.9789(10) 0.177(10) Uani 1 1 d . .
H83A H 0.6334 0.0911 0.9446 0.212 Uiso 1 1 calc R U
H83B H 0.6242 0.0619 1.0159 0.212 Uiso 1 1 calc R U
Cl1 Cl 0.7922(5) 0.0853(4) 1.0047(4) 0.179(3) Uani 1 1 d . .
Cl2 Cl 0.5826(5) -0.0673(4) 0.9458(3) 0.169(3) Uani 1 1 d . .
N1 N 0.3866(7) 0.4559(6) 0.2013(4) 0.039(2) Uani 1 1 d . .
N2 N 0.7485(8) 0.1533(6) 0.5797(5) 0.058(3) Uani 1 1 d D .
O1 O 0.2992(6) 0.2997(6) 0.1974(4) 0.071(3) Uani 1 1 d . .
O2 O 0.4782(6) 0.6135(5) 0.2025(4) 0.061(3) Uani 1 1 d . .
O3 O 0.6517(8) 0.1098(6) 0.4732(4) 0.082(3) Uani 1 1 d . .
O4 O 0.8605(7) 0.1976(5) 0.6830(4) 0.064(3) Uani 1 1 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'
O O 0.0106 0.0060 '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'
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_3
O1 C1 N1 120.8(10) .
O1 C1 C2 122.6(9) .
N1 C1 C2 116.6(10) .
C12 C2 C3 119.5(8) .
C12 C2 C1 121.0(9) .
C3 C2 C1 119.5(9) .
C4 C3 C2 118.6(9) .
C4 C3 C13 117.2(9) .
C2 C3 C13 124.1(8) .
C3 C4 C5 123.8(9) .
C3 C4 H4 118.1 .
C5 C4 H4 118.1 .
C4 C5 C6 118.0(8) .
C4 C5 C7 123.2(9) 2_565
C6 C5 C7 118.8(9) 2_565
C5 C6 C12 120.5(9) .
C5 C6 C7 120.2(8) .
C12 C6 C7 119.3(8) .
C8 C7 C6 116.9(8) .
C8 C7 C5 122.0(9) 2_565
C6 C7 C5 121.1(8) 2_565
C7 C8 C9 123.8(9) .
C7 C8 H8 118.1 .
C9 C8 H8 118.1 .
C10 C9 C8 119.4(9) .
C10 C9 C22 125.4(8) .
C8 C9 C22 115.1(9) .
C9 C10 C12 119.5(8) .
C9 C10 C11 121.0(9) .
C12 C10 C11 119.4(9) .
O2 C11 N1 121.5(9) .
O2 C11 C10 121.1(10) .
N1 C11 C10 117.4(9) .
C2 C12 C6 119.4(8) .
C2 C12 C10 119.7(8) .
C6 C12 C10 120.9(9) .
C14 C13 C18 120.3(12) .
C14 C13 C3 118.7(11) .
C18 C13 C3 120.5(11) .
C13 C14 C15 119.1(13) .
C13 C14 C19 121.3(11) .
C15 C14 C19 119.5(13) .
C16 C15 C14 122.1(14) .
C16 C15 H15 119.0 .
C14 C15 H15 119.0 .
C15 C16 C17 117.7(13) .
C15 C16 C20 119.5(16) .
C17 C16 C20 122.8(16) .
C16 C17 C18 124.4(14) .
C16 C17 H17 117.8 .
C18 C17 H17 117.8 .
C17 C18 C13 116.4(13) .
C17 C18 C21 123.5(13) .
C13 C18 C21 120.0(11) .
C14 C19 H19A 109.5 .
C14 C19 H19B 109.5 .
H19A C19 H19B 109.5 .
C14 C19 H19C 109.5 .
H19A C19 H19C 109.5 .
H19B C19 H19C 109.5 .
C16 C20 H20A 109.5 .
C16 C20 H20B 109.5 .
H20A C20 H20B 109.5 .
C16 C20 H20C 109.5 .
H20A C20 H20C 109.5 .
H20B C20 H20C 109.5 .
C18 C21 H21A 109.5 .
C18 C21 H21B 109.5 .
H21A C21 H21B 109.5 .
C18 C21 H21C 109.5 .
H21A C21 H21C 109.5 .
H21B C21 H21C 109.5 .
C27 C22 C23 122.7(11) .
C27 C22 C9 118.7(10) .
C23 C22 C9 118.6(11) .
C24 C23 C22 117.1(13) .
C24 C23 C28 122.1(12) .
C22 C23 C28 120.8(11) .
C25 C24 C23 122.7(14) .
C25 C24 H24 118.6 .
C23 C24 H24 118.6 .
C24 C25 C26 117.7(12) .
C24 C25 C29 118.3(16) .
C26 C25 C29 124.0(15) .
C25 C26 C27 122.8(14) .
C25 C26 H26 118.6 .
C27 C26 H26 118.6 .
C22 C27 C26 116.9(12) .
C22 C27 C30 122.5(11) .
C26 C27 C30 120.6(13) .
C23 C28 H28A 109.5 .
C23 C28 H28B 109.5 .
H28A C28 H28B 109.5 .
C23 C28 H28C 109.5 .
H28A C28 H28C 109.5 .
H28B C28 H28C 109.5 .
C25 C29 H29A 109.5 .
C25 C29 H29B 109.5 .
H29A C29 H29B 109.5 .
C25 C29 H29C 109.5 .
H29A C29 H29C 109.5 .
H29B C29 H29C 109.5 .
C27 C30 H30A 109.5 .
C27 C30 H30B 109.5 .
H30A C30 H30B 109.5 .
C27 C30 H30C 109.5 .
H30A C30 H30C 109.5 .
H30B C30 H30C 109.5 .
C32 C31 H31A 109.5 .
C32 C31 H31B 109.5 .
H31A C31 H31B 109.5 .
C32 C31 H31C 109.5 .
H31A C31 H31C 109.5 .
H31B C31 H31C 109.5 .
C33 C32 C31 110.3(13) .
C33 C32 H32A 109.6 .
C31 C32 H32A 109.6 .
C33 C32 H32B 109.6 .
C31 C32 H32B 109.6 .
H32A C32 H32B 108.1 .
C32 C33 C34 114.7(13) .
C32 C33 H33A 108.6 .
C34 C33 H33A 108.6 .
C32 C33 H33B 108.6 .
C34 C33 H33B 108.6 .
H33A C33 H33B 107.6 .
C35 C34 C33 110.9(11) .
C35 C34 H34A 109.5 .
C33 C34 H34A 109.5 .
C35 C34 H34B 109.5 .
C33 C34 H34B 109.5 .
H34A C34 H34B 108.0 .
C34 C35 C36 118.3(10) .
C34 C35 H35A 107.7 .
C36 C35 H35A 107.7 .
C34 C35 H35B 107.7 .
C36 C35 H35B 107.7 .
H35A C35 H35B 107.1 .
C35 C36 C37 117.7(10) .
C35 C36 N1 113.6(10) .
C37 C36 N1 111.8(9) .
C35 C36 H36 104.0 .
C37 C36 H36 104.0 .
N1 C36 H36 104.0 .
C38 C37 C36 118.4(11) .
C38 C37 H37A 107.7 .
C36 C37 H37A 107.7 .
C38 C37 H37B 107.7 .
C36 C37 H37B 107.7 .
H37A C37 H37B 107.1 .
C37 C38 C39 112.0(12) .
C37 C38 H38A 109.2 .
C39 C38 H38A 109.2 .
C37 C38 H38B 109.2 .
C39 C38 H38B 109.2 .
H38A C38 H38B 107.9 .
C38 C39 C40 112.4(13) .
C38 C39 H39A 109.1 .
C40 C39 H39A 109.1 .
C38 C39 H39B 109.1 .
C40 C39 H39B 109.1 .
H39A C39 H39B 107.9 .
C41 C40 C39 114.2(14) .
C41 C40 H40A 108.7 .
C39 C40 H40A 108.7 .
C41 C40 H40B 108.7 .
C39 C40 H40B 108.7 .
H40A C40 H40B 107.6 .
C40 C41 H41A 109.5 .
C40 C41 H41B 109.5 .
H41A C41 H41B 109.5 .
C40 C41 H41C 109.5 .
H41A C41 H41C 109.5 .
H41B C41 H41C 109.5 .
O3 C42 N2 120.1(10) .
O3 C42 C43 119.8(11) .
N2 C42 C43 119.9(10) .
C44 C43 C53 121.9(9) .
C44 C43 C42 121.6(9) .
C53 C43 C42 116.6(10) .
C43 C44 C45 117.5(9) .
C43 C44 C54 127.1(9) .
C45 C44 C54 115.4(10) .
C46 C45 C44 124.8(10) .
C46 C45 H45 117.6 .
C44 C45 H45 117.6 .
C45 C46 C47 117.3(9) .
C45 C46 C48 123.1(10) 2_766
C47 C46 C48 119.5(9) 2_766
C53 C47 C48 119.4(10) .
C53 C47 C46 119.8(9) .
C48 C47 C46 120.8(9) .
C49 C48 C47 119.5(9) .
C49 C48 C46 120.8(9) 2_766
C47 C48 C46 119.6(10) 2_766
C48 C49 C50 121.7(9) .
C48 C49 H49 119.1 .
C50 C49 H49 119.1 .
C51 C50 C49 118.9(10) .
C51 C50 C63 128.2(10) .
C49 C50 C63 112.8(9) .
C50 C51 C53 119.7(10) .
C50 C51 C52 119.4(11) .
C53 C51 C52 120.8(10) .
O4 C52 N2 117.9(10) .
O4 C52 C51 123.0(11) .
N2 C52 C51 119.2(11) .
C47 C53 C51 120.7(9) .
C47 C53 C43 118.4(10) .
C51 C53 C43 121.0(10) .
C59 C54 C55 121.4(10) .
C59 C54 C44 119.1(10) .
C55 C54 C44 119.1(11) .
C56 C55 C54 116.5(11) .
C56 C55 C60 121.1(11) .
C54 C55 C60 122.2(10) .
C57 C56 C55 124.5(11) .
C57 C56 H56 117.8 .
C55 C56 H56 117.8 .
C56 C57 C58 117.5(10) .
C56 C57 C61 121.7(11) .
C58 C57 C61 120.6(12) .
C57 C58 C59 120.9(12) .
C57 C58 H58 119.6 .
C59 C58 H58 119.6 .
C54 C59 C58 119.2(11) .
C54 C59 C62 122.6(10) .
C58 C59 C62 118.2(11) .
C55 C60 H60A 109.5 .
C55 C60 H60B 109.5 .
H60A C60 H60B 109.5 .
C55 C60 H60C 109.5 .
H60A C60 H60C 109.5 .
H60B C60 H60C 109.5 .
C57 C61 H61A 109.5 .
C57 C61 H61B 109.5 .
H61A C61 H61B 109.5 .
C57 C61 H61C 109.5 .
H61A C61 H61C 109.5 .
H61B C61 H61C 109.5 .
C59 C62 H62A 109.5 .
C59 C62 H62B 109.5 .
H62A C62 H62B 109.5 .
C59 C62 H62C 109.5 .
H62A C62 H62C 109.5 .
H62B C62 H62C 109.5 .
C64 C63 C68 121.2(10) .
C64 C63 C50 121.1(9) .
C68 C63 C50 117.6(10) .
C63 C64 C65 118.7(10) .
C63 C64 C69 121.8(10) .
C65 C64 C69 119.5(11) .
C66 C65 C64 123.2(11) .
C66 C65 H65 118.4 .
C64 C65 H65 118.4 .
C65 C66 C67 117.4(11) .
C65 C66 C70 122.2(11) .
C67 C66 C70 120.4(10) .
C66 C67 C68 121.4(11) .
C66 C67 H67 119.3 .
C68 C67 H67 119.3 .
C63 C68 C67 118.1(11) .
C63 C68 C71 123.3(10) .
C67 C68 C71 118.6(11) .
C64 C69 H69A 109.5 .
C64 C69 H69B 109.5 .
H69A C69 H69B 109.5 .
C64 C69 H69C 109.5 .
H69A C69 H69C 109.5 .
H69B C69 H69C 109.5 .
C66 C70 H70A 109.5 .
C66 C70 H70B 109.5 .
H70A C70 H70B 109.5 .
C66 C70 H70C 109.5 .
H70A C70 H70C 109.5 .
H70B C70 H70C 109.5 .
C68 C71 H71A 109.5 .
C68 C71 H71B 109.5 .
H71A C71 H71B 109.5 .
C68 C71 H71C 109.5 .
H71A C71 H71C 109.5 .
H71B C71 H71C 109.5 .
C73 C72 H72A 109.5 .
C73 C72 H72B 109.5 .
H72A C72 H72B 109.5 .
C73 C72 H72C 109.5 .
H72A C72 H72C 109.5 .
H72B C72 H72C 109.5 .
C72 C73 C74 128.9(13) .
C72 C73 H73A 105.1 .
C74 C73 H73A 105.1 .
C72 C73 H73B 105.1 .
C74 C73 H73B 105.1 .
H73A C73 H73B 105.9 .
C73 C74 C75 127.1(11) .
C73 C74 H74A 105.5 .
C75 C74 H74A 105.5 .
C73 C74 H74B 105.5 .
C75 C74 H74B 105.5 .
H74A C74 H74B 106.1 .
C76 C75 C74 128.4(9) .
C76 C75 H75A 105.2 .
C74 C75 H75A 105.2 .
C76 C75 H75B 105.2 .
C74 C75 H75B 105.2 .
H75A C75 H75B 105.9 .
C75 C76 C77 131.5(10) .
C75 C76 H76A 104.4 .
C77 C76 H76A 104.4 .
C75 C76 H76B 104.4 .
C77 C76 H76B 104.4 .
H76A C76 H76B 105.6 .
C76 C77 C78 128.5(10) .
C76 C77 N2 113.0(7) .
C78 C77 N2 113.4(8) .
C76 C77 H77 97.5 .
C78 C77 H77 97.5 .
N2 C77 H77 97.5 .
C79 C78 C77 130.0(12) .
C79 C78 H78A 104.8 .
C77 C78 H78A 104.8 .
C79 C78 H78B 104.8 .
C77 C78 H78B 104.8 .
H78A C78 H78B 105.8 .
C78 C79 C80 128.7(13) .
C78 C79 H79A 105.1 .
C80 C79 H79A 105.1 .
C78 C79 H79B 105.1 .
C80 C79 H79B 105.1 .
H79A C79 H79B 105.9 .
C81 C80 C79 127.4(13) .
C81 C80 H80A 105.5 .
C79 C80 H80A 105.5 .
C81 C80 H80B 105.5 .
C79 C80 H80B 105.5 .
H80A C80 H80B 106.0 .
C80 C81 C82 126.6(11) .
C80 C81 H81A 105.7 .
C82 C81 H81A 105.7 .
C80 C81 H81B 105.7 .
C82 C81 H81B 105.7 .
H81A C81 H81B 106.1 .
C81 C82 H82A 109.5 .
C81 C82 H82B 109.5 .
H82A C82 H82B 109.5 .
C81 C82 H82C 109.5 .
H82A C82 H82C 109.5 .
H82B C82 H82C 109.5 .
Cl1 C83 Cl2 124.1(15) .
Cl1 C83 H83A 106.3 .
Cl2 C83 H83A 106.3 .
Cl1 C83 H83B 106.3 .
Cl2 C83 H83B 106.3 .
H83A C83 H83B 106.4 .
C1 N1 C11 125.3(9) .
C1 N1 C36 116.0(9) .
C11 N1 C36 118.6(9) .
C42 N2 C52 121.5(9) .
C42 N2 C77 118.6(10) .
C52 N2 C77 119.9(10) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.206(12) .
C1 N1 1.372(12) .
C1 C2 1.491(14) .
C2 C12 1.406(13) .
C2 C3 1.429(13) .
C3 C4 1.361(13) .
C3 C13 1.510(15) .
C4 C5 1.387(13) .
C4 H4 0.9500 .
C5 C6 1.403(12) .
C5 C7 1.457(12) 2_565
C6 C12 1.417(12) .
C6 C7 1.434(12) .
C7 C8 1.384(12) .
C7 C5 1.457(12) 2_565
C8 C9 1.406(13) .
C8 H8 0.9500 .
C9 C10 1.367(13) .
C9 C22 1.523(13) .
C10 C12 1.419(12) .
C10 C11 1.495(13) .
C11 O2 1.221(11) .
C11 N1 1.389(13) .
C13 C14 1.388(15) .
C13 C18 1.403(15) .
C14 C15 1.398(16) .
C14 C19 1.518(16) .
C15 C16 1.353(17) .
C15 H15 0.9500 .
C16 C17 1.357(18) .
C16 C20 1.502(16) .
C17 C18 1.398(16) .
C17 H17 0.9500 .
C18 C21 1.456(16) .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 C27 1.357(16) .
C22 C23 1.388(15) .
C23 C24 1.381(16) .
C23 C28 1.491(17) .
C24 C25 1.350(18) .
C24 H24 0.9500 .
C25 C26 1.370(19) .
C25 C29 1.539(16) .
C26 C27 1.387(15) .
C26 H26 0.9500 .
C27 C30 1.477(16) .
C28 H28A 0.9800 .
C28 H28B 0.9800 .
C28 H28C 0.9800 .
C29 H29A 0.9800 .
C29 H29B 0.9800 .
C29 H29C 0.9800 .
C30 H30A 0.9800 .
C30 H30B 0.9800 .
C30 H30C 0.9800 .
C31 C32 1.521(18) .
C31 H31A 0.9800 .
C31 H31B 0.9800 .
C31 H31C 0.9800 .
C32 C33 1.405(17) .
C32 H32A 0.9900 .
C32 H32B 0.9900 .
C33 C34 1.569(16) .
C33 H33A 0.9900 .
C33 H33B 0.9900 .
C34 C35 1.476(16) .
C34 H34A 0.9900 .
C34 H34B 0.9900 .
C35 C36 1.480(16) .
C35 H35A 0.9900 .
C35 H35B 0.9900 .
C36 C37 1.501(16) .
C36 N1 1.523(12) .
C36 H36 1.0000 .
C37 C38 1.474(16) .
C37 H37A 0.9900 .
C37 H37B 0.9900 .
C38 C39 1.502(17) .
C38 H38A 0.9900 .
C38 H38B 0.9900 .
C39 C40 1.580(19) .
C39 H39A 0.9900 .
C39 H39B 0.9900 .
C40 C41 1.429(19) .
C40 H40A 0.9900 .
C40 H40B 0.9900 .
C41 H41A 0.9800 .
C41 H41B 0.9800 .
C41 H41C 0.9800 .
C42 O3 1.201(12) .
C42 N2 1.391(14) .
C42 C43 1.529(15) .
C43 C44 1.354(13) .
C43 C53 1.441(13) .
C44 C45 1.391(13) .
C44 C54 1.509(14) .
C45 C46 1.366(13) .
C45 H45 0.9500 .
C46 C47 1.439(13) .
C46 C48 1.473(13) 2_766
C47 C53 1.397(13) .
C47 C48 1.402(13) .
C48 C49 1.365(13) .
C48 C46 1.473(13) 2_766
C49 C50 1.428(14) .
C49 H49 0.9500 .
C50 C51 1.367(13) .
C50 C63 1.492(14) .
C51 C53 1.418(14) .
C51 C52 1.459(15) .
C52 O4 1.195(12) .
C52 N2 1.420(13) .
C54 C59 1.375(15) .
C54 C55 1.406(15) .
C55 C56 1.391(14) .
C55 C60 1.445(15) .
C56 C57 1.362(15) .
C56 H56 0.9500 .
C57 C58 1.393(15) .
C57 C61 1.477(14) .
C58 C59 1.406(14) .
C58 H58 0.9500 .
C59 C62 1.500(15) .
C60 H60A 0.9800 .
C60 H60B 0.9800 .
C60 H60C 0.9800 .
C61 H61A 0.9800 .
C61 H61B 0.9800 .
C61 H61C 0.9800 .
C62 H62A 0.9800 .
C62 H62B 0.9800 .
C62 H62C 0.9800 .
C63 C64 1.367(14) .
C63 C68 1.413(15) .
C64 C65 1.391(14) .
C64 C69 1.495(14) .
C65 C66 1.382(15) .
C65 H65 0.9500 .
C66 C67 1.395(15) .
C66 C70 1.475(14) .
C67 C68 1.413(14) .
C67 H67 0.9500 .
C68 C71 1.524(15) .
C69 H69A 0.9800 .
C69 H69B 0.9800 .
C69 H69C 0.9800 .
C70 H70A 0.9800 .
C70 H70B 0.9800 .
C70 H70C 0.9800 .
C71 H71A 0.9800 .
C71 H71B 0.9800 .
C71 H71C 0.9800 .
C72 C73 1.383(9) .
C72 H72A 0.9800 .
C72 H72B 0.9800 .
C72 H72C 0.9800 .
C73 C74 1.392(9) .
C73 H73A 0.9900 .
C73 H73B 0.9900 .
C74 C75 1.398(8) .
C74 H74A 0.9900 .
C74 H74B 0.9900 .
C75 C76 1.378(8) .
C75 H75A 0.9900 .
C75 H75B 0.9900 .
C76 C77 1.378(7) .
C76 H76A 0.9900 .
C76 H76B 0.9900 .
C77 C78 1.386(8) .
C77 N2 1.451(12) .
C77 H77 1.0000 .
C78 C79 1.377(9) .
C78 H78A 0.9900 .
C78 H78B 0.9900 .
C79 C80 1.396(9) .
C79 H79A 0.9900 .
C79 H79B 0.9900 .
C80 C81 1.383(9) .
C80 H80A 0.9900 .
C80 H80B 0.9900 .
C81 C82 1.419(7) .
C81 H81A 0.9900 .
C81 H81B 0.9900 .
C82 H82A 0.9800 .
C82 H82B 0.9800 .
C82 H82C 0.9800 .
C83 Cl1 1.546(18) .
C83 Cl2 1.744(17) .
C83 H83A 0.9900 .
C83 H83B 0.9900 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168339779
