Discovery and properties of a new indigoid structure type based on dimeric cis-indigos.
Hong, Hyejin; Conover, Cassidy M.; Hofsommer, Dillon T.; Sanz, Corey A.; Hicks, Robin G.; Organic & biomolecular chemistry 18 (2020) 5838–5842; doi:10.1039/d0ob01368d

data_7157609
_publ_section_title
;
 Discovery and properties of a new indigoid structure type based on
 dimeric cis-indigos.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5838
_journal_page_last               5842
_journal_paper_doi               10.1039/d0ob01368d
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C32 H18 N4 O4'
_chemical_formula_sum            'C32 H18 N4 O4'
_chemical_formula_weight         522.50
_chemical_name_common            'cis,trans-indigo dimer'
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-29
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-08-30 deposited with the CCDC.	2020-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.4500(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.8835(3)
_cell_length_b                   7.9818(2)
_cell_length_c                   18.7804(4)
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    90
_cell_measurement_theta_max      28.248
_cell_measurement_theta_min      2.777
_cell_volume                     2355.11(9)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      90
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            28111
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.259
_diffrn_reflns_theta_min         1.816
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0653 before and 0.0484 after correction. The Ratio of minimum to maximum transmission is 0.9202. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_description       tablet
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     369
_refine_ls_number_reflns         5833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0474
_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/[\s^2^(Fo^2^)+(0.0725P)^2^+0.4892P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1199
_refine_ls_wR_factor_ref         0.1297
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4560
_reflns_number_total             5833
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01368d2.cif
_cod_data_source_block           rh216_0m
_cod_depositor_comments
;
 Adding full bibliography for 7157609--7157611.cif.

2025-03-29
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C128 H72 N16 O16'
_cod_original_formula_weight         2090.01
_cod_original_formula_moiety         '4(C32 H18 N4 O4)'
_cod_original_formula_units_Z            1
_cod_database_code               7157609
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C12(H12), C12'(H12'), C15'(H15'), C13'(H13'), C14'(H14'),
 C13(H13), C7'(H7'), C7(H7), C6'(H6'), C4'(H4'), C4(H4), C5'(H5'), C6(H6),
 C5(H5)
;
_olex2_submission_original_sample_id rh216
_olex2_submission_special_instructions 'No special instructions were received'