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_7157149
_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         'C22 H16 N2 S'
_chemical_formula_sum            'C22 H18 N2 S'
_chemical_formula_weight         342.44
_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             2017-07-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_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                 101.041(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6081(3)
_cell_length_b                   15.1360(4)
_cell_length_c                   11.7745(3)
_cell_measurement_reflns_used    3060
_cell_measurement_temperature    199.94(12)
_cell_measurement_theta_max      71.6690
_cell_measurement_theta_min      3.8260
_cell_volume                     1680.65(8)
_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 (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      199.94(12)
_diffrn_detector_area_resol_mean 8.0851
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details
;
_refine_ls_extinction_coef        0.00005(11)
  1 omega -118.00  -56.00   1.0000    3.8800
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000   30.0000 62

  2 omega  -44.00  -10.00   1.0000    3.8800
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000   30.0000 34

  3 omega  -57.00   23.00   1.0000    3.8800
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   50.0000  -90.0000 80

  4 omega -113.00  -21.00   1.0000    3.8800
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000   60.0000 92

  5 omega   87.00  125.00   1.0000    3.8800
omega____ theta____ kappa____ phi______ frames
    -       54.7151   19.0000  120.0000 38

  6 omega   41.00   79.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303  -38.0000   60.0000 38

  7 omega   96.00  173.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303   64.0000 -180.0000 77

  8 omega   41.00   96.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303  -50.0000 -180.0000 55

  9 omega   62.00   89.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303  -25.0000 -180.0000 27

 10 omega   43.00  144.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303  -92.0000   60.0000 101

 11 omega   96.00  124.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303   64.0000  -30.0000 28

 12 omega  149.00  177.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303   64.0000  -30.0000 28

 13 omega   77.00  104.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303  -50.0000   60.0000 27

 14 omega   37.00   92.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303  -38.0000 -120.0000 55

 15 omega   60.00  141.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      109.4303  178.0000   90.0000 81
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0043590000
_diffrn_orient_matrix_UB_12      0.0465308000
_diffrn_orient_matrix_UB_13      0.1156740000
_diffrn_orient_matrix_UB_21      0.0367523000
_diffrn_orient_matrix_UB_22      -0.0878722000
_diffrn_orient_matrix_UB_23      0.0646746000
_diffrn_orient_matrix_UB_31      0.1591497000
_diffrn_orient_matrix_UB_32      0.0215932000
_diffrn_orient_matrix_UB_33      0.0144488000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5794
_diffrn_reflns_theta_full        71.92
_diffrn_reflns_theta_max         71.92
_diffrn_reflns_theta_min         4.69
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.739
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92665
_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    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_crystal_size_max          .34
_exptl_crystal_size_mid          .21
_exptl_crystal_size_min          .15
_refine_diff_density_max         1.105
_refine_diff_density_min         -0.856
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3159
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0730
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0746P)^2^+3.1372P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1773
_refine_ls_wR_factor_ref         0.1856
_reflns_number_gt                2662
_reflns_number_total             3159
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ob01762c2.cif
_cod_data_source_block           exp_289
_cod_depositor_comments
'Adding full bibliography for 7157149--7157156.cif.'
_cod_original_cell_volume        1680.64(8)
_cod_database_code               7157149
_chemical_oxdiff_formula         'C H N S'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C21(H21), C17(H17), C16(H16), C8(H8), C18(H18), C19(H19), C9(H9), C25(H25),
 C22(H22), C15(H15), C13(H13), C14(H14), C24(H24), C11(H11), C10(H10), C23(H23)
;
_olex2_date_sample_data_collection 2014-01-03
_olex2_submission_special_instructions 'No special instructions were received'