#------------------------------------------------------------------------------
#$Date: 2022-05-14 01:39:43 +0300 (Sat, 14 May 2022) $
#$Revision: 275421 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/49/7244937.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7244937
loop_
_publ_author_name
'Akai, Ryota'
'Oka, Kouki'
'Nishida, Ryunosuke'
'Tohnai, Norimitsu'
_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         'C20 H12 O6 S4, 2(C4 H12 N)'
_chemical_formula_sum            'C28 H36 N2 O6 S4'
_chemical_formula_weight         624.83
_chemical_name_systematic        BTDS-isoBuA
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2b8s3j
_audit_creation_date             2021-07-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-02-20 deposited with the CCDC.	2022-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.855(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   27.9234(7)
_cell_length_b                   7.4749(2)
_cell_length_c                   7.6043(2)
_cell_measurement_reflns_used    2408
_cell_measurement_temperature    293
_cell_measurement_theta_max      73.2480
_cell_measurement_theta_min      4.7720
_cell_volume                     1581.51(7)
_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      293
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  14.00   0.50    1.00    --    0.00 -19.00   0.00  202
  2  ω    -39.00   5.00   0.50    1.00    --    0.00 -37.00  90.00   88
  3  ω    -72.00 -43.00   0.50    1.00    --    0.00 -37.00  90.00   58
  4  ω    140.00 166.00   0.50    5.00    --   94.90  45.00  90.00   52
  5  ω    130.00 172.00   0.50    5.00    --   94.90  15.00-150.00   84
  6  ω     74.00 184.00   0.50    5.00    --   94.90  77.00-120.00  220
  7  ω     25.00 111.00   0.50    5.00    --   94.90 -61.00 120.00  172
  8  ω     18.00 119.00   0.50    5.00    --   94.90 -77.00  90.00  202
  9  ω    104.00 130.00   0.50    5.00    --   94.90  45.00  90.00   52
 10  ω     75.00 174.00   0.50    5.00    --   94.90  45.00 -30.00  198
 11  ω     69.00 112.00   0.50    5.00    --   94.90 -45.00 120.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0238005000
_diffrn_orient_matrix_UB_12      -0.1821774000
_diffrn_orient_matrix_UB_13      0.0293335000
_diffrn_orient_matrix_UB_21      -0.0488495000
_diffrn_orient_matrix_UB_22      0.0755088000
_diffrn_orient_matrix_UB_23      -0.0756701000
_diffrn_orient_matrix_UB_31      0.0108988000
_diffrn_orient_matrix_UB_32      -0.0595104000
_diffrn_orient_matrix_UB_33      -0.1863545000
_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  0.0564
_diffrn_reflns_av_unetI/netI     0.0667
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8176
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.292
_diffrn_reflns_theta_min         3.177
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70006
_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            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       plate
_exptl_crystal_F_000             660
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3124
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0530
_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/[σ²(Fo²)+(0.0638P)²+0.5068P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1441
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2320
_reflns_number_total             3124
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce00336h2.cif
_cod_data_source_block           exp_3004
_cod_database_code               7244937
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNSO
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00I(H00I)
2.b Secondary CH2 refined with riding coordinates:
 C00H(H00A,H00H)
2.c Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G)
2.d Idealised Me refined as rotating group:
 N8(H8A,H8B,H8C), C00J(H00J,H00K,H00L), C00K(H00M,H00N,H00O)
;
_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 1.522
_oxdiff_exptl_absorpt_empirical_full_min 0.543
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.79044(2) 0.49672(9) 0.53902(9) 0.0354(2) Uani 1 1 d . . . . .
S002 S 0.57532(3) 0.44238(12) 0.96207(11) 0.0486(2) Uani 1 1 d . . . . .
O003 O 0.79239(8) 0.6334(3) 0.4034(3) 0.0468(5) Uani 1 1 d . . . . .
O004 O 0.80022(7) 0.3208(3) 0.4713(3) 0.0486(5) Uani 1 1 d . . . . .
O005 O 0.81968(8) 0.5401(3) 0.6982(3) 0.0487(5) Uani 1 1 d . . . . .
N8 N 0.82630(9) -0.0341(3) 0.5763(3) 0.0419(6) Uani 1 1 d . . . . .
H8A H 0.809909 -0.092758 0.488882 0.050 Uiso 1 1 calc R U . . .
H8B H 0.823398 0.083139 0.557859 0.050 Uiso 1 1 calc R U . . .
H8C H 0.814729 -0.062039 0.678278 0.050 Uiso 1 1 calc R U . . .
C10 C 0.73014(11) 0.4962(4) 0.5947(4) 0.0388(6) Uani 1 1 d . . . . .
C008 C 0.63629(11) 0.5020(4) 0.6958(4) 0.0436(7) Uani 1 1 d . . . . .
C009 C 0.51614(11) 0.5110(4) 0.9312(4) 0.0449(7) Uani 1 1 d . . . . .
C00A C 0.58749(11) 0.5142(4) 0.7546(4) 0.0449(7) Uani 1 1 d . . . . .
C00B C 0.71734(11) 0.3895(5) 0.7310(5) 0.0534(9) Uani 1 1 d . . . . .
H00B H 0.740094 0.315054 0.789790 0.064 Uiso 1 1 calc R U . . .
C00C C 0.67098(11) 0.3926(5) 0.7806(5) 0.0543(9) Uani 1 1 d . . . . .
H00C H 0.662854 0.319771 0.872664 0.065 Uiso 1 1 calc R U . . .
C00D C 0.54729(12) 0.5856(5) 0.6682(5) 0.0561(9) Uani 1 1 d . . . . .
H00D H 0.546525 0.630876 0.554054 0.067 Uiso 1 1 calc R U . . .
C00E C 0.50704(12) 0.5847(5) 0.7673(5) 0.0548(9) Uani 1 1 d . . . . .
H00E H 0.477172 0.629639 0.725453 0.066 Uiso 1 1 calc R U . . .
C00F C 0.69534(12) 0.6018(5) 0.5062(5) 0.0601(10) Uani 1 1 d . . . . .
H00F H 0.703231 0.671819 0.411786 0.072 Uiso 1 1 calc R U . . .
C00G C 0.64938(13) 0.6045(5) 0.5561(5) 0.0638(10) Uani 1 1 d . . . . .
H00G H 0.626506 0.676548 0.494822 0.077 Uiso 1 1 calc R U . . .
C00H C 0.87785(13) -0.0852(5) 0.5827(5) 0.0642(10) Uani 1 1 d . . . . .
H00A H 0.880215 -0.214379 0.591678 0.077 Uiso 1 1 calc R U . . .
H00H H 0.890243 -0.050328 0.472326 0.077 Uiso 1 1 calc R U . . .
C00I C 0.90858(16) -0.0052(7) 0.7294(6) 0.0784(13) Uani 1 1 d . . . . .
H00I H 0.893797 -0.029280 0.839343 0.094 Uiso 1 1 calc R U . . .
C00J C 0.9123(2) 0.1998(8) 0.7074(8) 0.117(2) Uani 1 1 d . . . . .
H00J H 0.925203 0.226386 0.597294 0.176 Uiso 1 1 calc R U . . .
H00K H 0.933072 0.248113 0.802755 0.176 Uiso 1 1 calc R U . . .
H00L H 0.880930 0.252100 0.708521 0.176 Uiso 1 1 calc R U . . .
C00K C 0.95794(19) -0.0853(10) 0.7449(10) 0.143(3) Uani 1 1 d . . . . .
H00M H 0.955496 -0.213343 0.748978 0.215 Uiso 1 1 calc R U . . .
H00N H 0.975421 -0.043038 0.850882 0.215 Uiso 1 1 calc R U . . .
H00O H 0.974538 -0.050935 0.644624 0.215 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O003 S001 C10 105.34(13) . . ?
O004 S001 O003 111.47(13) . . ?
O004 S001 C10 107.16(13) . . ?
O005 S001 O003 112.65(13) . . ?
O005 S001 O004 113.19(13) . . ?
O005 S001 C10 106.43(13) . . ?
C00A S002 C009 92.48(16) . . ?
H8A N8 H8B 109.5 . . ?
H8A N8 H8C 109.5 . . ?
H8B N8 H8C 109.5 . . ?
C00H N8 H8A 109.5 . . ?
C00H N8 H8B 109.5 . . ?
C00H N8 H8C 109.5 . . ?
C00B C10 S001 119.6(2) . . ?
C00B C10 C00F 118.7(3) . . ?
C00F C10 S001 121.7(2) . . ?
C00C C008 C00A 121.6(3) . . ?
C00G C008 C00A 120.7(3) . . ?
C00G C008 C00C 117.7(3) . . ?
C009 C009 S002 121.0(3) 3_667 . ?
C00E C009 S002 110.2(2) . . ?
C00E C009 C009 128.8(4) . 3_667 ?
C008 C00A S002 121.1(2) . . ?
C00D C00A S002 110.2(3) . . ?
C00D C00A C008 128.6(3) . . ?
C10 C00B H00B 119.8 . . ?
C10 C00B C00C 120.3(3) . . ?
C00C C00B H00B 119.8 . . ?
C008 C00C H00C 119.4 . . ?
C00B C00C C008 121.2(3) . . ?
C00B C00C H00C 119.4 . . ?
C00A C00D H00D 123.1 . . ?
C00A C00D C00E 113.8(3) . . ?
C00E C00D H00D 123.1 . . ?
C009 C00E C00D 113.3(3) . . ?
C009 C00E H00E 123.3 . . ?
C00D C00E H00E 123.3 . . ?
C10 C00F H00F 119.6 . . ?
C00G C00F C10 120.7(3) . . ?
C00G C00F H00F 119.6 . . ?
C008 C00G H00G 119.4 . . ?
C00F C00G C008 121.3(3) . . ?
C00F C00G H00G 119.4 . . ?
N8 C00H H00A 108.6 . . ?
N8 C00H H00H 108.6 . . ?
H00A C00H H00H 107.5 . . ?
C00I C00H N8 114.9(3) . . ?
C00I C00H H00A 108.6 . . ?
C00I C00H H00H 108.6 . . ?
C00H C00I H00I 108.1 . . ?
C00H C00I C00J 111.1(4) . . ?
C00H C00I C00K 111.7(5) . . ?
C00J C00I H00I 108.1 . . ?
C00K C00I H00I 108.1 . . ?
C00K C00I C00J 109.6(5) . . ?
C00I C00J H00J 109.5 . . ?
C00I C00J H00K 109.5 . . ?
C00I C00J H00L 109.5 . . ?
H00J C00J H00K 109.5 . . ?
H00J C00J H00L 109.5 . . ?
H00K C00J H00L 109.5 . . ?
C00I C00K H00M 109.5 . . ?
C00I C00K H00N 109.5 . . ?
C00I C00K H00O 109.5 . . ?
H00M C00K H00N 109.5 . . ?
H00M C00K H00O 109.5 . . ?
H00N C00K H00O 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 O003 1.456(2) . ?
S001 O004 1.447(2) . ?
S001 O005 1.439(2) . ?
S001 C10 1.770(3) . ?
S002 C009 1.727(3) . ?
S002 C00A 1.727(3) . ?
N8 H8A 0.8900 . ?
N8 H8B 0.8900 . ?
N8 H8C 0.8900 . ?
N8 C00H 1.486(4) . ?
C10 C00B 1.378(4) . ?
C10 C00F 1.382(4) . ?
C008 C00A 1.473(4) . ?
C008 C00C 1.385(4) . ?
C008 C00G 1.384(5) . ?
C009 C009 1.448(6) 3_667 ?
C009 C00E 1.366(5) . ?
C00A C00D 1.361(4) . ?
C00B H00B 0.9300 . ?
C00B C00C 1.379(4) . ?
C00C H00C 0.9300 . ?
C00D H00D 0.9300 . ?
C00D C00E 1.405(5) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00F C00G 1.369(5) . ?
C00G H00G 0.9300 . ?
C00H H00A 0.9700 . ?
C00H H00H 0.9700 . ?
C00H C00I 1.475(6) . ?
C00I H00I 0.9800 . ?
C00I C00J 1.546(7) . ?
C00I C00K 1.498(7) . ?
C00J H00J 0.9600 . ?
C00J H00K 0.9600 . ?
C00J H00L 0.9600 . ?
C00K H00M 0.9600 . ?
C00K H00N 0.9600 . ?
C00K H00O 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S001 C10 C00B C00C 177.5(3) . . . . ?
S001 C10 C00F C00G -177.4(3) . . . . ?
S002 C009 C00E C00D 0.0(4) . . . . ?
S002 C00A C00D C00E 0.5(4) . . . . ?
O003 S001 C10 C00B -175.0(3) . . . . ?
O003 S001 C10 C00F 4.3(3) . . . . ?
O004 S001 C10 C00B 66.2(3) . . . . ?
O004 S001 C10 C00F -114.5(3) . . . . ?
O005 S001 C10 C00B -55.1(3) . . . . ?
O005 S001 C10 C00F 124.1(3) . . . . ?
N8 C00H C00I C00J -66.6(5) . . . . ?
N8 C00H C00I C00K 170.7(4) . . . . ?
C10 C00B C00C C008 -0.1(6) . . . . ?
C10 C00F C00G C008 -0.1(6) . . . . ?
C008 C00A C00D C00E -176.5(3) . . . . ?
C009 S002 C00A C008 176.8(3) . . . . ?
C009 S002 C00A C00D -0.5(3) . . . . ?
C009 C009 C00E C00D 179.4(4) 3_667 . . . ?
C00A S002 C009 C009 -179.2(4) . . . 3_667 ?
C00A S002 C009 C00E 0.3(3) . . . . ?
C00A C008 C00C C00B -176.3(3) . . . . ?
C00A C008 C00G C00F 176.4(4) . . . . ?
C00A C00D C00E C009 -0.3(5) . . . . ?
C00B C10 C00F C00G 1.9(6) . . . . ?
C00C C008 C00A S002 17.4(5) . . . . ?
C00C C008 C00A C00D -165.9(4) . . . . ?
C00C C008 C00G C00F -1.8(6) . . . . ?
C00F C10 C00B C00C -1.8(5) . . . . ?
C00G C008 C00A S002 -160.7(3) . . . . ?
C00G C008 C00A C00D 16.0(6) . . . . ?
C00G C008 C00C C00B 1.8(6) . . . . ?
