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_7157610
_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         '0.53(C42 H20 N4 O6), 0.8(C7 H8)'
_chemical_formula_sum            'C28 H17.07 N2.13 O3.2'
_chemical_formula_weight         434.57
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-31
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2019-08-30 deposited with the CCDC.	2020-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.498(4)
_cell_angle_gamma                90
_cell_formula_units_Z            30
_cell_length_a                   39.337(3)
_cell_length_b                   13.8936(10)
_cell_length_c                   28.683(2)
_cell_measurement_reflns_used    9994
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      27.888
_cell_measurement_theta_min      2.283
_cell_volume                     15647(2)
_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 0.995
_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  0.0512
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       51
_diffrn_reflns_limit_h_min       -51
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            79517
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.932
_diffrn_reflns_theta_min         1.423
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_correction_T_min  0.9085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0764 before and 0.0571 after correction.
The Ratio of minimum to maximum transmission is 0.9185.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       prism
_exptl_crystal_F_000             6768
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1213
_refine_ls_number_reflns         18680
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0522
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1395
_refine_ls_wR_factor_ref         0.1575
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13381
_reflns_number_total             18680
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01368d2.cif
_cod_data_source_block           rh180
_cod_depositor_comments
;Adding full bibliography for 7157609--7157611.cif.

 Adding full bibliography for 7157609--7157611.cif.
;
_cod_original_cell_volume        15647.3(19)
_cod_original_formula_sum        'C28 H17.07 N2.13 O3.20'
_cod_database_code               7157610
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.979
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C69)=Sof(H69)=Sof(C70)=Sof(H70)=Sof(C71)=Sof(H71)=Sof(C72)=Sof(H72)=
 Sof(C73)=Sof(H73)=Sof(C74)=Sof(C75)=Sof(H75A)=Sof(H75B)=Sof(H75C)=1-FVAR(1)
 Sof(C62)=Sof(H62)=Sof(C63)=Sof(H63)=Sof(C64)=Sof(H64)=Sof(C65)=Sof(H65)=
 Sof(C66)=Sof(H66)=Sof(C67)=Sof(C68)=Sof(H68A)=Sof(H68B)=Sof(H68C)=FVAR(1)
 Fixed Sof: C61(0.5) H61A(0.5) H61B(0.5) H61C(0.5) C55(0.5) H55(0.5) C56(0.5)
 H56(0.5) C57(0.5) H57(0.5) C58(0.5) H58(0.5) C59(0.5) H59(0.5) C60(0.5)
 H54A(0.5) H54B(0.5) H54C(0.5)
3.a Free rotating group:
 C61(C55,C56,C57,C58,C59,C60)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15),
 C20(H20), C21(H21), C22(H22), C23(H23), C28(H28), C29(H29), C30(H30), C31(H31),
  C36(H36), C37(H37), C38(H38), C39(H39), C4A(H4A), C5A(H5A), C6A(H6A),
 C7A(H7A), C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A), C20A(H20A),
 C21A(H21A), C22A(H22A), C23A(H23A), C28A(H28A), C29A(H29A), C30A(H30A),
 C31A(H31A), C36A(H36A), C37A(H37A), C38A(H38A), C39A(H39A), C62(H62), C63(H63),
  C64(H64), C65(H65), C66(H66), C43(H43), C44(H44), C45(H45), C47(H47),
 C48(H48), C55(H55), C56(H56), C57(H57), C58(H58), C59(H59), C69(H69), C70(H70),
  C71(H71), C72(H72), C73(H73), C50(H50), C51(H51), C52(H52)
3.c Idealised Me refined as rotating group:
 C68(H68A,H68B,H68C), C49(H49A,H49B,H49C), C61(H61A,H61B,H61C), C75(H75A,H75B,
 H75C), C54(H54A,H54B,H54C)
;
_shelx_res_checksum              58571
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'