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_7157611
_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, 0.5(H2 O)'
_chemical_formula_sum            'C32 H19 N4 O4.5'
_chemical_formula_weight         531.51
_chemical_name_common            'cis,cis-indigo dimer'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2019-08-30 deposited with the CCDC.	2020-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.574(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.7629(15)
_cell_length_b                   10.8917(6)
_cell_length_c                   17.5795(9)
_cell_measurement_reflns_used    5550
_cell_measurement_temperature    90
_cell_measurement_theta_max      55.946
_cell_measurement_theta_min      3.474
_cell_volume                     4872.1(5)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0697
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15242
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        56.030
_diffrn_reflns_theta_max         56.030
_diffrn_reflns_theta_min         3.474
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.813
_exptl_absorpt_correction_T_max  0.7510
_exptl_absorpt_correction_T_min  0.6718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0731 before and 0.0647 after correction. The Ratio of minimum to maximum transmission is 0.8945. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       rod
_exptl_crystal_F_000             2200
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.00024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         3176
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0382
_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/[\s^2^(Fo^2^)+(0.0374P)^2^+3.6742P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0914
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2517
_reflns_number_total             3176
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01368d2.cif
_cod_data_source_block           cu_rh220_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            'C256 H152 N32 O36'
_cod_original_formula_weight         4252.09
_cod_original_formula_moiety         '8(C32 H18 N4 O4), 4(H2 O)'
_cod_original_formula_units_Z            1
_cod_database_code               7157611
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.916
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C12(H12), C4(H4), C15'(H15'), C12'(H12'), C6(H6), C5(H5), C15(H15),
 C14'(H14'), C14(H14), C13'(H13'), C7'(H7'), C6'(H6'), C13(H13), C5'(H5')
;
_olex2_submission_original_sample_id rh220/EH-253-71
_olex2_submission_special_instructions 'No special instructions were received'