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_7157154
_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 Se'
_chemical_formula_sum            'C22 H16 N2 Se'
_chemical_formula_weight         387.33
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-02-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_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                 101.610(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6424(15)
_cell_length_b                   15.1758(17)
_cell_length_c                   11.7826(13)
_cell_measurement_reflns_used    1789
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      28.8600
_cell_measurement_theta_min      3.7890
_cell_volume                     1688.9(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1702
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 1.0
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -48.00  47.00   1.00    1.53    --   19.60 -77.00 120.00   95
  2  \w    -46.00 -20.00   1.00    1.53    --   19.60 -77.00-150.00   26
  3  \w     25.00  51.00   1.00    1.53    --   19.60 -77.00-150.00   26
  4  \w      5.00  89.00   1.00    1.53    --   19.60  57.00-120.00   84
  5  \w     -7.00  18.00   1.00    1.53    --  -20.38 -99.00  60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0709991000
_diffrn_orient_matrix_UB_12      0.0024328000
_diffrn_orient_matrix_UB_13      -0.0310003000
_diffrn_orient_matrix_UB_21      -0.0243506000
_diffrn_orient_matrix_UB_22      -0.0109588000
_diffrn_orient_matrix_UB_23      0.0511662000
_diffrn_orient_matrix_UB_31      -0.0020668000
_diffrn_orient_matrix_UB_32      0.0453965000
_diffrn_orient_matrix_UB_33      0.0139349000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.1266
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7713
_diffrn_reflns_theta_full        28.82
_diffrn_reflns_theta_max         28.82
_diffrn_reflns_theta_min         3.33
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.229
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       clear
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.583
_refine_diff_density_min         -1.928
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       0.0046(8)
_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   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3808
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.1725
_refine_ls_R_factor_gt           0.0958
_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^)+(0.0536P)^2^+6.6236P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1745
_refine_ls_wR_factor_ref         0.2162
_reflns_number_gt                2120
_reflns_number_total             4408
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9ob01762c2.cif
_cod_data_source_block           exp_1358
_cod_depositor_comments
'Adding full bibliography for 7157149--7157156.cif.'
_cod_database_code               7157154
_chemical_oxdiff_formula         'C H N Se'
_reflns_odcompleteness_completeness 99.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C21(H21), C16(H16), C14(H14), C10(H10), C13(H13), C8(H8), C24(H24),
 C25(H25), C19(H19), C11(H11), C9(H9), C15(H15), C22(H22), C17(H17), C23(H23)
;
_olex2_date_sample_data_collection 2018-01-23
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.837
_oxdiff_exptl_absorpt_empirical_full_min 0.632