#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/38/1553851.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_1553851
loop_
_publ_author_name
'Zhang, Yuehong'
'Wang, Chiming'
'Chen, Xin'
'Pan, Houhe'
'Qi, Dongdong'
'Wang, Kang'
'Jiang, Jianzhuang'
_publ_section_title
;
 Novel, linear oligoisoindole compounds with a conjugated electronic
 structure
;
_journal_issue                   12
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2364
_journal_paper_doi               10.1039/C7QO00631D
_journal_volume                  4
_journal_year                    2017
_chemical_formula_sum            'C100 H96 Cl6 N6 O10'
_chemical_formula_weight         1754.53
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-05-18 deposited with the CCDC.
2017-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                100.836(3)
_cell_angle_beta                 99.601(4)
_cell_angle_gamma                93.264(3)
_cell_formula_units_Z            1
_cell_length_a                   9.8074(5)
_cell_length_b                   13.2321(5)
_cell_length_c                   17.7176(7)
_cell_measurement_reflns_used    6448
_cell_measurement_temperature    150
_cell_measurement_theta_max      66.8846
_cell_measurement_theta_min      3.4121
_cell_volume                     2217.36(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14923
_diffrn_reflns_theta_full        66.99
_diffrn_reflns_theta_max         66.99
_diffrn_reflns_theta_min         3.41
_exptl_absorpt_coefficient_mu    2.281
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31053
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_refine_diff_density_max         1.209
_refine_diff_density_min         -0.800
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     560
_refine_ls_number_reflns         7686
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0658
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1072P)²+2.3162P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1830
_refine_ls_wR_factor_ref         0.1934
_reflns_number_gt                6507
_reflns_number_total             7686
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7qo00631d2.cif
_cod_data_source_block           zyh
_cod_original_cell_volume        2217.35(17)
_cod_database_code               1553851
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.1577(2) 1.26116(14) 0.12092(11) 0.0375(4) Uani 1 1 d .
O3 O 0.3219(2) 0.54566(15) 0.34152(12) 0.0383(5) Uani 1 1 d .
O2 O 0.1100(2) 1.15510(16) 0.22433(12) 0.0397(5) Uani 1 1 d .
O4 O 0.5220(2) 0.43141(15) 0.32168(12) 0.0401(5) Uani 1 1 d .
N1 N 0.5026(2) 0.90321(16) 0.06394(12) 0.0304(5) Uani 1 1 d .
N2 N 0.4169(2) 0.83365(17) 0.16633(12) 0.0310(5) Uani 1 1 d .
C1 C 0.4298(3) 0.9053(2) 0.12089(15) 0.0296(5) Uani 1 1 d .
C2 C 0.4945(3) 0.7561(2) 0.16308(15) 0.0311(6) Uani 1 1 d .
C3 C 0.3522(3) 0.9961(2) 0.13085(15) 0.0300(5) Uani 1 1 d .
N3 N 0.5988(3) 0.73770(19) 0.12375(14) 0.0385(6) Uani 1 1 d .
H3 H 0.6216 0.7749 0.0921 0.046 Uiso 1 1 calc R
C4 C 0.4054(3) 0.5739(2) 0.29262(15) 0.0316(6) Uani 1 1 d .
C5 C 0.4725(3) 0.99029(19) 0.03095(15) 0.0289(5) Uani 1 1 d .
C6 C 0.3897(3) 0.6562(2) 0.25586(15) 0.0310(5) Uani 1 1 d .
H6 H 0.3189 0.6989 0.2631 0.037 Uiso 1 1 calc R
C7 C 0.3090(3) 1.1389(2) 0.06666(15) 0.0313(6) Uani 1 1 d .
H7 H 0.3221 1.1757 0.0282 0.038 Uiso 1 1 calc R
C8 C 0.2013(3) 1.1161(2) 0.17765(16) 0.0333(6) Uani 1 1 d .
C9 C 0.4832(3) 0.6740(2) 0.20727(15) 0.0307(5) Uani 1 1 d .
C10 C 0.2225(3) 1.1710(2) 0.11921(16) 0.0329(6) Uani 1 1 d .
C11 C 0.6059(3) 0.5284(2) 0.23299(17) 0.0356(6) Uani 1 1 d .
H11 H 0.6769 0.4860 0.2255 0.043 Uiso 1 1 calc R
C12 C 0.5151(3) 0.5108(2) 0.28184(16) 0.0333(6) Uani 1 1 d .
C13 C 0.3761(3) 1.0496(2) 0.07311(14) 0.0296(5) Uani 1 1 d .
C14 C 0.5884(3) 0.6109(2) 0.19539(16) 0.0331(6) Uani 1 1 d .
C15 C 0.2660(3) 1.0279(2) 0.18383(15) 0.0325(6) Uani 1 1 d .
H15 H 0.2526 0.9908 0.2221 0.039 Uiso 1 1 calc R
C16 C 0.6812(3) 0.3067(2) 0.28603(18) 0.0399(6) Uani 1 1 d .
C17 C 0.6517(3) 0.3925(2) 0.33727(17) 0.0356(6) Uani 1 1 d .
C18 C 0.1470(3) 1.3710(2) 0.02876(17) 0.0395(6) Uani 1 1 d .
C19 C 0.1135(3) 1.1196(2) 0.29474(17) 0.0383(6) Uani 1 1 d .
C20 C 0.7408(3) 0.4389(2) 0.40589(18) 0.0395(6) Uani 1 1 d .
C21 C 0.6701(3) 0.6481(2) 0.14009(18) 0.0413(7) Uani 1 1 d .
H21A H 0.7666 0.6677 0.1644 0.050 Uiso 1 1 calc R
H21B H 0.6656 0.5961 0.0930 0.050 Uiso 1 1 calc R
C22 C 0.2161(3) 0.6088(2) 0.35853(17) 0.0371(6) Uani 1 1 d .
C23 C 0.0831(3) 0.5781(3) 0.31668(19) 0.0438(7) Uani 1 1 d .
C24 C 0.0216(3) 1.0370(3) 0.2969(2) 0.0479(8) Uani 1 1 d .
C25 C 0.0949(3) 1.2830(2) 0.05008(17) 0.0377(6) Uani 1 1 d .
C26 C 0.3038(4) 1.2619(3) 0.3545(2) 0.0493(8) Uani 1 1 d .
H26A H 0.3741 1.2356 0.3263 0.074 Uiso 1 1 calc R
H26B H 0.3466 1.2976 0.4060 0.074 Uiso 1 1 calc R
H26C H 0.2538 1.3087 0.3274 0.074 Uiso 1 1 calc R
C27 C 0.8649(3) 0.3950(3) 0.4236(2) 0.0456(7) Uani 1 1 d .
H27 H 0.9263 0.4231 0.4698 0.055 Uiso 1 1 calc R
C28 C 0.2057(3) 1.1742(2) 0.36009(18) 0.0410(7) Uani 1 1 d .
C29 C -0.0213(3) 0.6391(3) 0.3384(2) 0.0539(9) Uani 1 1 d .
H29 H -0.1123 0.6213 0.3121 0.065 Uiso 1 1 calc R
C30 C 0.2490(3) 0.6937(2) 0.41976(18) 0.0421(7) Uani 1 1 d .
C31 C 0.2733(4) 1.4357(3) 0.0773(2) 0.0512(8) Uani 1 1 d .
H31A H 0.2557 1.4613 0.1289 0.077 Uiso 1 1 calc R
H31B H 0.2945 1.4927 0.0536 0.077 Uiso 1 1 calc R
H31C H 0.3505 1.3943 0.0806 0.077 Uiso 1 1 calc R
C32 C 0.8089(3) 0.2676(2) 0.3061(2) 0.0469(7) Uani 1 1 d .
H32 H 0.8336 0.2114 0.2728 0.056 Uiso 1 1 calc R
C33 C 0.2029(4) 1.1436(3) 0.43109(19) 0.0480(8) Uani 1 1 d .
H33 H 0.2623 1.1786 0.4761 0.058 Uiso 1 1 calc R
C34 C 0.0074(4) 0.7245(3) 0.3977(2) 0.0571(9) Uani 1 1 d .
H34 H -0.0637 0.7640 0.4108 0.069 Uiso 1 1 calc R
C35 C -0.0234(4) 1.2217(3) 0.0077(2) 0.0504(8) Uani 1 1 d .
C36 C 0.8980(3) 0.3110(3) 0.3742(2) 0.0497(8) Uani 1 1 d .
H36 H 0.9817 0.2831 0.3869 0.060 Uiso 1 1 calc R
C37 C 0.7051(4) 0.5321(3) 0.4595(2) 0.0534(8) Uani 1 1 d .
H37A H 0.7130 0.5916 0.4363 0.080 Uiso 1 1 calc R
H37B H 0.7678 0.5434 0.5087 0.080 Uiso 1 1 calc R
H37C H 0.6116 0.5206 0.4678 0.080 Uiso 1 1 calc R
C38 C 0.0771(3) 1.3974(3) -0.03936(18) 0.0458(7) Uani 1 1 d .
H38 H 0.1074 1.4572 -0.0543 0.055 Uiso 1 1 calc R
C39 C 0.3942(4) 0.7178(3) 0.4661(2) 0.0528(8) Uani 1 1 d .
H39A H 0.3978 0.7785 0.5060 0.079 Uiso 1 1 calc R
H39B H 0.4572 0.7298 0.4320 0.079 Uiso 1 1 calc R
H39C H 0.4204 0.6606 0.4898 0.079 Uiso 1 1 calc R
C40 C 0.1422(4) 0.7523(3) 0.4382(2) 0.0527(8) Uani 1 1 d .
H40 H 0.1609 0.8107 0.4780 0.063 Uiso 1 1 calc R
C41 C 0.1130(4) 1.0621(3) 0.4349(2) 0.0566(9) Uani 1 1 d .
H41 H 0.1127 1.0423 0.4826 0.068 Uiso 1 1 calc R
C42 C -0.0358(4) 1.3356(3) -0.0844(2) 0.0547(9) Uani 1 1 d .
H42 H -0.0791 1.3528 -0.1305 0.066 Uiso 1 1 calc R
C43 C 0.5814(4) 0.2571(3) 0.2133(2) 0.0536(8) Uani 1 1 d .
H43A H 0.5087 0.2158 0.2265 0.080 Uiso 1 1 calc R
H43B H 0.6295 0.2139 0.1786 0.080 Uiso 1 1 calc R
H43C H 0.5420 0.3096 0.1880 0.080 Uiso 1 1 calc R
C44 C 0.0241(4) 1.0096(3) 0.3699(2) 0.0547(9) Uani 1 1 d .
H44 H -0.0359 0.9547 0.3741 0.066 Uiso 1 1 calc R
C45 C -0.0855(4) 1.2488(3) -0.0621(2) 0.0601(9) Uani 1 1 d .
H45 H -0.1612 1.2073 -0.0936 0.072 Uiso 1 1 calc R
C46 C 0.0519(4) 0.4840(3) 0.2525(2) 0.0582(9) Uani 1 1 d .
H46A H 0.1105 0.4888 0.2148 0.087 Uiso 1 1 calc R
H46B H -0.0436 0.4794 0.2277 0.087 Uiso 1 1 calc R
H46C H 0.0689 0.4235 0.2740 0.087 Uiso 1 1 calc R
C47 C -0.0743(4) 0.9807(3) 0.2250(2) 0.0632(10) Uani 1 1 d .
H47A H -0.1353 1.0275 0.2050 0.095 Uiso 1 1 calc R
H47B H -0.1281 0.9252 0.2375 0.095 Uiso 1 1 calc R
H47C H -0.0211 0.9531 0.1863 0.095 Uiso 1 1 calc R
C48 C -0.0850(4) 1.1330(3) 0.0370(3) 0.0714(11) Uani 1 1 d .
H48A H -0.0292 1.0758 0.0293 0.107 Uiso 1 1 calc R
H48B H -0.1777 1.1124 0.0086 0.107 Uiso 1 1 calc R
H48C H -0.0872 1.1540 0.0916 0.107 Uiso 1 1 calc R
O5 O 0.2272(4) 0.6085(3) 0.9054(2) 0.0961(11) Uani 1 1 d .
H5 H 0.1734 0.6527 0.8990 0.144 Uiso 1 1 calc R
C49 C 0.3454(6) 0.6532(4) 0.9621(3) 0.0880(14) Uani 1 1 d .
H49A H 0.3676 0.7229 0.9569 0.132 Uiso 1 1 calc R
H49B H 0.4227 0.6136 0.9544 0.132 Uiso 1 1 calc R
H49C H 0.3258 0.6535 1.0135 0.132 Uiso 1 1 calc R
Cl3 Cl 0.66642(9) 0.85899(7) 0.36152(6) 0.0647(3) Uani 1 1 d .
Cl1 Cl 0.41598(17) 0.95512(12) 0.39242(10) 0.1090(5) Uani 1 1 d .
C51 C 0.5481(4) 0.9487(3) 0.3391(2) 0.0506(8) Uani 1 1 d .
H51 H 0.5043 0.9246 0.2842 0.061 Uiso 1 1 calc R
Cl2 Cl 0.63436(15) 1.06980(8) 0.34552(9) 0.0895(4) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C10 O1 C25 117.9(2) .
C4 O3 C22 117.5(2) .
C8 O2 C19 116.6(2) .
C12 O4 C17 116.9(2) .
C1 N1 C5 106.6(2) .
C2 N2 C1 120.4(2) .
N1 C1 N2 128.5(2) .
N1 C1 C3 112.1(2) .
N2 C1 C3 119.4(2) .
N2 C2 N3 128.8(2) .
N2 C2 C9 123.7(2) .
N3 C2 C9 107.4(2) .
C15 C3 C13 123.1(2) .
C15 C3 C1 130.3(2) .
C13 C3 C1 106.5(2) .
C2 N3 C21 113.2(2) .
O3 C4 C6 125.2(2) .
O3 C4 C12 114.7(2) .
C6 C4 C12 120.1(2) .
C5 C5 N1 121.9(3) 2_675
C5 C5 C13 128.7(3) 2_675
N1 C5 C13 109.4(2) .
C4 C6 C9 118.1(2) .
C10 C7 C13 118.1(2) .
C15 C8 O2 124.1(2) .
C15 C8 C10 120.4(2) .
O2 C8 C10 115.5(2) .
C14 C9 C6 121.7(2) .
C14 C9 C2 108.1(2) .
C6 C9 C2 130.2(2) .
O1 C10 C7 122.8(2) .
O1 C10 C8 115.3(2) .
C7 C10 C8 121.7(2) .
C12 C11 C14 118.2(2) .
O4 C12 C11 123.3(2) .
O4 C12 C4 115.4(2) .
C11 C12 C4 121.3(2) .
C3 C13 C7 119.1(2) .
C3 C13 C5 105.3(2) .
C7 C13 C5 135.6(2) .
C9 C14 C11 120.6(2) .
C9 C14 C21 109.6(2) .
C11 C14 C21 129.8(2) .
C8 C15 C3 117.6(2) .
C17 C16 C32 116.8(3) .
C17 C16 C43 122.2(3) .
C32 C16 C43 121.0(3) .
C20 C17 C16 123.5(3) .
C20 C17 O4 117.5(3) .
C16 C17 O4 118.9(3) .
C25 C18 C38 117.5(3) .
C25 C18 C31 121.1(3) .
C38 C18 C31 121.4(3) .
C24 C19 C28 123.5(3) .
C24 C19 O2 119.2(3) .
C28 C19 O2 117.2(3) .
C17 C20 C27 117.1(3) .
C17 C20 C37 121.7(3) .
C27 C20 C37 121.2(3) .
N3 C21 C14 101.6(2) .
C23 C22 C30 124.0(3) .
C23 C22 O3 117.7(3) .
C30 C22 O3 118.1(3) .
C22 C23 C29 116.3(3) .
C22 C23 C46 122.1(3) .
C29 C23 C46 121.7(3) .
C19 C24 C44 116.5(3) .
C19 C24 C47 121.3(3) .
C44 C24 C47 122.2(3) .
C18 C25 O1 117.5(3) .
C18 C25 C35 123.1(3) .
O1 C25 C35 119.1(3) .
C36 C27 C20 121.0(3) .
C19 C28 C33 117.4(3) .
C19 C28 C26 121.4(3) .
C33 C28 C26 121.3(3) .
C34 C29 C23 121.4(3) .
C40 C30 C22 117.4(3) .
C40 C30 C39 121.7(3) .
C22 C30 C39 120.9(3) .
C36 C32 C16 120.9(3) .
C41 C33 C28 120.4(3) .
C29 C34 C40 120.4(3) .
C25 C35 C45 116.9(3) .
C25 C35 C48 121.5(3) .
C45 C35 C48 121.5(3) .
C27 C36 C32 120.6(3) .
C42 C38 C18 120.6(3) .
C30 C40 C34 120.5(3) .
C44 C41 C33 121.0(3) .
C45 C42 C38 120.8(3) .
C41 C44 C24 121.2(3) .
C42 C45 C35 120.9(3) .
Cl1 C51 Cl2 112.2(2) .
Cl1 C51 Cl3 113.6(2) .
Cl2 C51 Cl3 110.9(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C10 1.381(3) .
O1 C25 1.392(3) .
O3 C4 1.372(3) .
O3 C22 1.405(3) .
O2 C8 1.375(3) .
O2 C19 1.409(3) .
O4 C12 1.370(3) .
O4 C17 1.403(3) .
N1 C1 1.326(3) .
N1 C5 1.411(3) .
N2 C2 1.310(3) .
N2 C1 1.368(3) .
C1 C3 1.456(4) .
C2 N3 1.340(3) .
C2 C9 1.462(4) .
C3 C15 1.389(4) .
C3 C13 1.392(4) .
N3 C21 1.461(3) .
C4 C6 1.374(4) .
C4 C12 1.415(4) .
C5 C5 1.359(5) 2_675
C5 C13 1.473(4) .
C6 C9 1.397(4) .
C7 C10 1.387(4) .
C7 C13 1.398(4) .
C8 C15 1.374(4) .
C8 C10 1.407(4) .
C9 C14 1.382(4) .
C11 C12 1.380(4) .
C11 C14 1.387(4) .
C14 C21 1.498(4) .
C16 C17 1.390(4) .
C16 C32 1.399(4) .
C16 C43 1.497(5) .
C17 C20 1.387(4) .
C18 C25 1.386(4) .
C18 C38 1.399(4) .
C18 C31 1.502(5) .
C19 C24 1.387(5) .
C19 C28 1.393(5) .
C20 C27 1.392(4) .
C20 C37 1.505(4) .
C22 C23 1.386(4) .
C22 C30 1.388(5) .
C23 C29 1.399(5) .
C23 C46 1.498(5) .
C24 C44 1.405(5) .
C24 C47 1.491(5) .
C25 C35 1.393(5) .
C26 C28 1.493(5) .
C27 C36 1.370(5) .
C28 C33 1.396(4) .
C29 C34 1.370(6) .
C30 C40 1.384(5) .
C30 C39 1.504(5) .
C32 C36 1.371(5) .
C33 C41 1.373(5) .
C34 C40 1.388(5) .
C35 C45 1.403(5) .
C35 C48 1.505(5) .
C38 C42 1.374(5) .
C41 C44 1.365(5) .
C42 C45 1.373(6) .
O5 C49 1.419(6) .
Cl3 C51 1.759(3) .
Cl1 C51 1.723(4) .
C51 Cl2 1.744(4) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168304088
