#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/25/4502559.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_4502559
loop_
_publ_author_name
'Shiota, Naoki'
'Kinuta, Takafumi'
'Sato, Tomohiro'
'Tajima, Nobuo'
'Kuroda, Reiko'
'Matsubara, Yoshio'
'Imai, Yoshitane'
_publ_section_title
;
 Preparation of Supramolecular Thiophene Host System Showing Solid-State
 Fluorescence by Using Chiral (1R,2S)-2-Amino-1,2-diphenylethanol
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1341
_journal_paper_doi               10.1021/cg901364a
_journal_volume                  10
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H25 N O4 S'
_chemical_formula_weight         387.48
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0493(9)
_cell_length_b                   14.410(2)
_cell_length_c                   22.861(3)
_cell_measurement_reflns_used    3629
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      27.77
_cell_measurement_theta_min      1.67
_cell_volume                     1992.8(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      115(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_sigmaI/netI    0.0804
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            12142
_diffrn_reflns_theta_full        27.77
_diffrn_reflns_theta_max         27.77
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.9906
_exptl_absorpt_correction_T_min  0.9035
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.21(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4401
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0792
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0767P)²+1.7032P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1679
_refine_ls_wR_factor_ref         0.1772
_reflns_number_gt                3629
_reflns_number_total             4401
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg901364a_si_002.cif
_cod_data_source_block           imai911_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               4502559
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.7629(2) 0.70637(8) 1.23651(5) 0.0308(3) Uani 1 1 d .
C2 C 0.6044(7) 0.6977(2) 1.17516(16) 0.0163(8) Uani 1 1 d .
C3 C 0.3828(6) 0.6694(2) 1.18831(13) 0.0061(6) Uani 1 1 d .
H3 H 0.2670 0.6600 1.1609 0.007 Uiso 1 1 calc R
C4 C 0.3678(8) 0.6577(3) 1.25134(19) 0.0307(11) Uani 1 1 d .
H4 H 0.2361 0.6381 1.2703 0.037 Uiso 1 1 calc R
C5 C 0.5544(9) 0.6768(3) 1.28062(18) 0.0339(12) Uani 1 1 d .
H5 H 0.5667 0.6737 1.3220 0.041 Uiso 1 1 calc R
C6 C 0.6987(7) 0.7219(2) 1.11742(16) 0.0153(8) Uani 1 1 d .
O7 O 0.9003(5) 0.74474(19) 1.11486(12) 0.0223(6) Uani 1 1 d .
O8 O 0.5762(5) 0.71726(19) 1.07317(11) 0.0203(6) Uani 1 1 d .
C11 C 0.1128(7) 0.4460(3) 0.94432(15) 0.0180(8) Uani 1 1 d .
C12 C 0.3098(7) 0.4195(3) 0.91890(18) 0.0245(10) Uani 1 1 d .
H12 H 0.4164 0.4653 0.9090 0.029 Uiso 1 1 calc R
C13 C 0.3544(7) 0.3261(3) 0.90751(19) 0.0285(10) Uani 1 1 d .
H13 H 0.4904 0.3084 0.8899 0.034 Uiso 1 1 calc R
C14 C 0.2004(9) 0.2600(3) 0.92188(18) 0.0304(11) Uani 1 1 d .
H14 H 0.2309 0.1963 0.9149 0.036 Uiso 1 1 calc R
C15 C 0.0020(8) 0.2856(3) 0.94644(17) 0.0257(10) Uani 1 1 d .
H15 H -0.1050 0.2395 0.9555 0.031 Uiso 1 1 calc R
C16 C -0.0432(8) 0.3783(3) 0.95812(17) 0.0222(9) Uani 1 1 d .
H16 H -0.1799 0.3955 0.9754 0.027 Uiso 1 1 calc R
C17 C 0.0746(7) 0.5484(3) 0.95854(16) 0.0168(8) Uani 1 1 d .
H17 H 0.1209 0.5866 0.9242 0.020 Uiso 1 1 calc R
O18 O -0.1484(5) 0.5691(2) 0.97206(12) 0.0215(7) Uani 1 1 d .
H18 H -0.2208 0.5751 0.9409 0.032 Uiso 1 1 calc R
C19 C 0.1783(7) 0.5184(3) 1.06596(16) 0.0156(8) Uani 1 1 d .
C20 C -0.0234(7) 0.5202(3) 1.09486(17) 0.0188(9) Uani 1 1 d .
H20 H -0.1408 0.5569 1.0798 0.023 Uiso 1 1 calc R
C21 C -0.0557(8) 0.4686(3) 1.14585(17) 0.0216(9) Uani 1 1 d .
H21 H -0.1934 0.4706 1.1658 0.026 Uiso 1 1 calc R
C22 C 0.1132(9) 0.4151(3) 1.16671(18) 0.0297(11) Uani 1 1 d .
H22 H 0.0919 0.3796 1.2013 0.036 Uiso 1 1 calc R
C23 C 0.3137(8) 0.4118(3) 1.13842(18) 0.0249(10) Uani 1 1 d .
H23 H 0.4297 0.3740 1.1532 0.030 Uiso 1 1 calc R
C24 C 0.3455(7) 0.4640(3) 1.08799(17) 0.0200(9) Uani 1 1 d .
H24 H 0.4841 0.4621 1.0685 0.024 Uiso 1 1 calc R
C25 C 0.2152(6) 0.5759(2) 1.01142(15) 0.0142(8) Uani 1 1 d .
H25 H 0.3737 0.5683 1.0000 0.017 Uiso 1 1 calc R
N26 N 0.1793(5) 0.6767(2) 1.02496(14) 0.0170(7) Uani 1 1 d .
H26A H 0.0525 0.6834 1.0460 0.025 Uiso 1 1 calc R
H26B H 0.1680 0.7092 0.9910 0.025 Uiso 1 1 calc R
H26C H 0.2955 0.6986 1.0461 0.025 Uiso 1 1 calc R
O31 O 0.1408(6) 0.8988(2) 1.12906(13) 0.0366(9) Uani 1 1 d .
H31 H 0.0190 0.8709 1.1295 0.055 Uiso 1 1 calc R
C31 C 0.1785(11) 0.9410(6) 1.1845(3) 0.072(2) Uani 1 1 d .
H31A H 0.1468 1.0082 1.1813 0.086 Uiso 1 1 calc R
H31B H 0.0731 0.9144 1.2131 0.086 Uiso 1 1 calc R
C32 C 0.3954(13) 0.9295(4) 1.2063(3) 0.064(2) Uani 1 1 d .
H32A H 0.4238 0.8635 1.2133 0.096 Uiso 1 1 calc R
H32B H 0.4111 0.9638 1.2431 0.096 Uiso 1 1 calc R
H32C H 0.5017 0.9533 1.1776 0.096 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
C5 S1 C2 93.1(2)
C3 C2 C6 127.9(3)
C3 C2 S1 112.0(3)
C6 C2 S1 120.0(3)
C2 C3 C4 107.4(3)
C5 C4 C3 114.8(4)
C4 C5 S1 112.7(3)
O8 C6 O7 123.1(4)
O8 C6 C2 118.6(4)
O7 C6 C2 118.3(4)
C12 C11 C16 119.1(4)
C12 C11 C17 119.2(4)
C16 C11 C17 121.7(4)
C11 C12 C13 120.8(4)
C14 C13 C12 119.5(4)
C13 C14 C15 120.2(4)
C14 C15 C16 120.6(4)
C15 C16 C11 119.7(4)
O18 C17 C11 113.2(3)
O18 C17 C25 107.6(3)
C11 C17 C25 109.5(3)
C24 C19 C20 118.9(4)
C24 C19 C25 120.3(4)
C20 C19 C25 120.8(4)
C19 C20 C21 120.7(4)
C22 C21 C20 119.2(4)
C21 C22 C23 121.0(4)
C22 C23 C24 119.5(4)
C19 C24 C23 120.7(4)
N26 C25 C19 109.8(3)
N26 C25 C17 109.4(3)
C19 C25 C17 115.3(3)
C32 C31 O31 114.3(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C5 1.670(6)
S1 C2 1.703(4)
C2 C3 1.433(5)
C2 C6 1.480(5)
C3 C4 1.454(5)
C4 C5 1.341(7)
C6 O8 1.256(5)
C6 O7 1.264(5)
C11 C12 1.380(6)
C11 C16 1.393(6)
C11 C17 1.528(6)
C12 C13 1.398(6)
C13 C14 1.372(7)
C14 C15 1.375(7)
C15 C16 1.390(6)
C17 O18 1.416(5)
C17 C25 1.530(5)
C19 C24 1.375(6)
C19 C20 1.388(6)
C19 C25 1.514(5)
C20 C21 1.396(5)
C21 C22 1.366(6)
C22 C23 1.375(7)
C23 C24 1.390(6)
C25 N26 1.502(5)
O31 C31 1.425(6)
C31 C32 1.413(9)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139144968
