Systematic arrangement control of functional organic molecules
Akai, Ryota; Oka, Kouki; Nishida, Ryunosuke; Tohnai, Norimitsu; CrystEngComm  (2022) –; doi:10.1039/D2CE00336H

data_7244941
_publ_section_title
;
 Systematic arrangement control of functional organic molecules
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00336H
_journal_year                    2022
_chemical_formula_moiety         '2(C10 H7 S)'
_chemical_formula_sum            'C20 H14 S2'
_chemical_formula_weight         318.43
_chemical_name_systematic        BTDPh
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2b8vwc
_audit_creation_date             2022-01-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-02-21 deposited with the CCDC.	2022-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                86.3680(10)
_cell_angle_beta                 89.9800(10)
_cell_angle_gamma                89.8680(10)
_cell_formula_units_Z            2
_cell_length_a                   5.68780(10)
_cell_length_b                   7.86580(10)
_cell_length_c                   16.9636(2)
_cell_measurement_reflns_used    23281
_cell_measurement_temperature    213
_cell_measurement_theta_max      74.0990
_cell_measurement_theta_min      5.2290
_cell_volume                     757.410(19)
_computing_cell_refinement       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      213
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_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    -89.00  18.00   0.50    1.00    --    0.00 -19.00  90.00  214
  2  \w    -29.00  89.00   0.50    1.00    --    0.00  77.00 120.00  236
  3  \w    -18.00  89.00   0.50    1.00    --    0.00  19.00  90.00  214
  4  \w      5.00 114.00   0.50    2.00    --   94.90 -45.00  60.00  218
  5  \w      5.00 126.00   0.50    2.00    --   94.90 -82.00 -60.00  242
  6  \w      5.00 118.00   0.50    2.00    --   94.90 -61.00-150.00  226
  7  \w      5.00 126.00   0.50    2.00    --   94.90 -82.00-150.00  242
  8  \w     71.00 184.00   0.50    2.00    --   94.90  15.00 120.00  226
  9  \w      5.00 126.00   0.50    2.00    --   94.90 -82.00  60.00  242
 10  \w     65.00 184.00   0.50    2.00    --   94.90  77.00 150.00  238
 11  \w      5.00 118.00   0.50    2.00    --   94.90 -61.00-120.00  226
 12  \w     71.00 184.00   0.50    2.00    --   94.90  15.00  30.00  226
 13  \w      5.00 124.00   0.50    2.00    --   94.90 -77.00  90.00  238
 14  \w      5.00 126.00   0.50    2.00    --   94.90 -82.00-120.00  242
 15  \w      5.00 111.00   0.50    2.00    --   94.90 -30.00 -90.00  212
 16  \w    -22.00  89.00   0.50    1.00    --    0.00  57.00   0.00  222
 17  \w    -17.00  89.00   0.50    1.00    --    0.00  37.00 -90.00  212
 18  \w    -18.00  89.00   0.50    1.00    --    0.00  19.00-150.00  214
 19  \w     65.00 184.00   0.50    2.00    --   94.90  77.00-180.00  238
 20  \w     63.00 184.00   0.50    2.00    --   94.90  82.00 -60.00  242
 21  \w     75.00 184.00   0.50    2.00    --   94.90  45.00 120.00  218
 22  \w     78.00 184.00   0.50    2.00    --   94.90  30.00 -30.00  212
 23  \w     63.00 184.00   0.50    2.00    --   94.90  82.00   0.00  242
 24  \w     63.00 184.00   0.50    2.00    --   94.90  82.00  30.00  242
 25  \w     63.00 184.00   0.50    2.00    --   94.90  82.00 120.00  242
 26  \w     75.00 184.00   0.50    2.00    --   94.90  45.00 -90.00  218
 27  \w     65.00 184.00   0.50    2.00    --   94.90  77.00-150.00  238
 28  \w     65.00 184.00   0.50    2.00    --   94.90  77.00 -90.00  238
 29  \w     65.00 184.00   0.50    2.00    --   94.90  77.00  60.00  238
 30  \w     71.00 184.00   0.50    2.00    --   94.90  15.00 -90.00  226
 31  \w    -17.00  89.00   0.50    1.00    --    0.00  37.00 -60.00  212
 32  \w    -17.00  89.00   0.50    1.00    --    0.00  37.00   0.00  212
 33  \w    -17.00  89.00   0.50    1.00    --    0.00  37.00  30.00  212
 34  \w     63.00 184.00   0.50    2.00    --   94.90  82.00-120.00  242
 35  \w     75.00 184.00   0.50    2.00    --   94.90  45.00 150.00  218
 36  \w     65.00 184.00   0.50    2.00    --   94.90  77.00 -30.00  238
 37  \w     63.00 184.00   0.50    2.00    --   94.90  82.00  90.00  242
 38  \w     71.00 184.00   0.50    2.00    --   94.90  61.00-150.00  226
 39  \w     65.00 184.00   0.50    2.00    --   94.90  77.00  30.00  238
 40  \w     75.00 184.00   0.50    2.00    --   94.90  45.00 -30.00  218
 41  \w     71.00 184.00   0.50    2.00    --   94.90  61.00-180.00  226
 42  \w     71.00 184.00   0.50    2.00    --   94.90  61.00  90.00  226
 43  \w     63.00 184.00   0.50    2.00    --   94.90  82.00-150.00  242
 44  \w     65.00 184.00   0.50    2.00    --   94.90  77.00   0.00  238
 45  \w     71.00 184.00   0.50    2.00    --   94.90  61.00   0.00  226
 46  \w    -18.00  89.00   0.50    1.00    --    0.00  19.00  60.00  214
 47  \w    -89.00  18.00   0.50    1.00    --    0.00 -19.00 -60.00  214
 48  \w    -89.00  22.00   0.50    1.00    --    0.00 -57.00 120.00  222
 49  \w     65.00 184.00   0.50    2.00    --   94.90  77.00  90.00  238
 50  \w      5.00 118.00   0.50    2.00    --   94.90 -61.00  60.00  226
 51  \w     75.00 184.00   0.50    2.00    --   94.90  45.00-180.00  218
 52  \w     75.00 184.00   0.50    2.00    --   94.90  45.00   0.00  218
 53  \w     75.00 184.00   0.50    2.00    --   94.90  45.00 -60.00  218
 54  \w     75.00 184.00   0.50    2.00    --   94.90  45.00  60.00  218
 55  \w     75.00 184.00   0.50    2.00    --   94.90  45.00  90.00  218
 56  \w     75.00 184.00   0.50    2.00    --   94.90  45.00-120.00  218
 57  \w     65.00 184.00   0.50    2.00    --   94.90  77.00-120.00  238
 58  \w     65.00 184.00   0.50    2.00    --   94.90  77.00 -60.00  238
 59  \w     65.00 184.00   0.50    2.00    --   94.90  77.00 120.00  238
 60  \w     63.00 184.00   0.50    2.00    --   94.90  82.00 -90.00  242
 61  \w    -89.00  89.00   0.50    1.00    --    0.00   0.00-120.00  356
 62  \w    -89.00  89.00   0.50    1.00    --    0.00   0.00-150.00  356
 63  \w    -89.00  89.00   0.50    1.00    --    0.00   0.00-180.00  356
 64  \w     78.00 184.00   0.50    2.00    --   94.90  30.00  30.00  212
 65  \w     78.00 184.00   0.50    2.00    --   94.90  30.00-150.00  212
 66  \w     71.00 184.00   0.50    2.00    --   94.90  61.00 -60.00  226
 67  \w     63.00 184.00   0.50    2.00    --   94.90  82.00-180.00  242
 68  \w     71.00 184.00   0.50    2.00    --   94.90  61.00 150.00  226
 69  \w     63.00 184.00   0.50    2.00    --   94.90  82.00  60.00  242
 70  \w     63.00 184.00   0.50    2.00    --   94.90  82.00 150.00  242
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0001226000
_diffrn_orient_matrix_UB_12      0.0383505000
_diffrn_orient_matrix_UB_13      -0.0901913000
_diffrn_orient_matrix_UB_21      -0.0436634000
_diffrn_orient_matrix_UB_22      -0.1898750000
_diffrn_orient_matrix_UB_23      -0.0119394000
_diffrn_orient_matrix_UB_31      -0.2673106000
_diffrn_orient_matrix_UB_32      0.0314854000
_diffrn_orient_matrix_UB_33      0.0019279000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            49945
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.460
_diffrn_reflns_theta_min         2.610
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       plate
_exptl_crystal_F_000             332
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.221
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3036
_refine_ls_number_restraints     174
_refine_ls_restrained_S_all      1.187
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0594
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+2.2733P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1446
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2849
_reflns_number_total             3036
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00336h2.cif
_cod_data_source_block           exp_3312
_cod_database_code               7244941
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHS
_reflns_odcompleteness_completeness 99.85
_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. Rigid bond restraints
 C00G, S002, C003, C00C, C006, C007, C00A, C00E, C00I, C00M, C00J
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C00K, S001, C004, C009, C005, C008, C00B, C00D, C00F, C00L, C00H
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C00G \\sim S002 \\sim C003 \\sim C00C \\sim C006 \\sim C007 \\sim C00A \\sim
C00E \\sim C00I \\sim C00M \\sim C00J: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 1.7A
C00K \\sim S001 \\sim C004 \\sim C009 \\sim C005 \\sim C008 \\sim C00B \\sim
C00D \\sim C00F \\sim C00L \\sim C00H: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 1.7A
4.a Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00K(H00K), C00H(H00H), C00L(H00L), C00F(H00F), C007(H007),
 C008(H008), C00A(H00A), C00B(H00B), C00G(H00G), C00M(H00M), C00J(H00J),
 C00I(H00I), C00E(H00E)
4.b Fitted hexagon refined as free rotating group:
 C005(C00D,C00K,C00H,C00L,C00F), C00G(C00M,C00J,C00I,C00E,C006)
;
_shelx_res_checksum              94670
_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 1.744
_oxdiff_exptl_absorpt_empirical_full_min 0.632