Benzochalcogendiazole-based conjugated molecules: investigating the effects of substituents and heteroatom juggling.
Patel, Heta A.; Bhanvadia, Viraj J.; Mande, Hemant M.; Zade, Sanjio S.; Patel, Arun L.; Organic & biomolecular chemistry 17 (2019) 9467–; doi:10.1039/c9ob01762c

data_7157150
_publ_section_title
;
 Benzochalcogendiazole-based conjugated molecules: investigating the
 effects of substituents and heteroatom juggling.
;
_journal_issue                   43
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9467
_journal_paper_doi               10.1039/c9ob01762c
_journal_volume                  17
_journal_year                    2019
_chemical_formula_moiety         'C20 H14 N4 S, C8 H6 O4'
_chemical_formula_sum            'C28 H20 N4 O4 S'
_chemical_formula_weight         508.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-10-26
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2018-06-19 deposited with the CCDC.    2019-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 103.164(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.0978(6)
_cell_length_b                   8.4281(4)
_cell_length_c                   21.7783(9)
_cell_measurement_reflns_used    2112
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.1000
_cell_measurement_theta_min      4.7720
_cell_volume                     2340.92(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.0851
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -50.00   30.00   1.0000   28.2700
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000   30.0000 80

  2 omega -119.00  -75.00   1.0000   28.2700
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000  -60.0000 44

  3 omega -113.00  -10.00   1.0000   28.2700
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -25.0000   30.0000 103

  4 omega   41.00   80.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303  -38.0000  150.0000 39

  5 omega   64.00   93.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303  -25.0000   90.0000 29

  6 omega   37.00   81.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303 -111.0000    0.0000 44

  7 omega   37.00   91.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303  -25.0000 -180.0000 54

  8 omega   84.00  113.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303 -111.0000    0.0000 29

  9 omega   41.00   92.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303  -38.0000    0.0000 51

 10 omega   95.00  176.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303   50.0000  -60.0000 81

 11 omega   39.00  145.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303  -92.0000 -180.0000 106
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0876903000
_diffrn_orient_matrix_UB_12      -0.0132629000
_diffrn_orient_matrix_UB_13      -0.0363802000
_diffrn_orient_matrix_UB_21      0.0811649000
_diffrn_orient_matrix_UB_22      -0.0257987000
_diffrn_orient_matrix_UB_23      0.0625928000
_diffrn_orient_matrix_UB_31      -0.0179801000
_diffrn_orient_matrix_UB_32      -0.1803778000
_diffrn_orient_matrix_UB_33      -0.0062471000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6730
_diffrn_reflns_theta_full        71.76
_diffrn_reflns_theta_max         71.76
_diffrn_reflns_theta_min         4.17
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.608
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.976
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.064
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         4452
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0749
_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/[\s^2^(Fo^2^)+(0.1001P)^2^+1.6271P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1957
_refine_ls_wR_factor_ref         0.2210
_reflns_number_gt                3017
_reflns_number_total             4584
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ob01762c2.cif
_cod_data_source_block           exp_381
_cod_depositor_comments
'Adding full bibliography for 7157149--7157156.cif.'
_cod_original_cell_volume        2340.93(18)
_cod_database_code               7157150
_reflns_odcompleteness_completeness 98.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H37(0.081) H34(0.102) H10(0.055) H16(0.057) H13(0.06) H30(0.056)
 H17(0.057) H28(0.057) H9(0.055) H11(0.057) H14(0.059) H18(0.072) H8(0.058)
 H27(0.061) H31(0.059) H21(0.095) H19(0.08) H24(0.095) H22(0.096)
 Fixed X: H37(-0.0027) H34(0.1953) H10(0.8182) H16(1.0308) H13(0.7057) H30(-
 0.0759) H17(0.9339) H28(0.1812) H9(0.7928) H11(0.6733) H14(0.8077) H18(0.5537)
 H8(0.6998) H27(0.2694) H31(0.0118) H21(0.243) H19(0.3859) H24(0.4012)
 H22(0.1631)
 Fixed Y: H37(0.9298) H34(0.3052) H10(1.1095) H16(1.4207) H13(1.2758)
 H30(0.69) H17(1.2523) H28(0.7291) H9(0.9532) H11(1.1081) H14(1.4424)
 H18(0.6494) H8(0.7899) H27(0.5613) H31(0.5208) H21(0.4831) H19(0.6346)
 H24(0.3326) H22(0.3255)
 Fixed Z: H37(0.3895) H34(0.7169) H10(0.6313) H16(0.7726) H13(0.7928)
 H30(0.5519) H17(0.6984) H28(0.4826) H9(0.5411) H11(0.7027) H14(0.8625)
 H18(0.4125) H8(0.4648) H27(0.5598) H31(0.6291) H21(0.4044) H19(0.4598)
 H24(0.2466) H22(0.3255)
;
_olex2_submission_special_instructions 'No special instructions were received'