#------------------------------------------------------------------------------
#$Date: 2025-04-05 05:24:24 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/38/1573850.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_1573850
loop_
_publ_author_name
'Lu, Jiachen'
'Ok, Kang Min'
_publ_section_title
;
 Synergistic engineering of ultraviolet metal-free crystals with
 exceptional birefringence via pyridine-derived dimers.
;
_journal_issue                   11
_journal_name_full               'Chemical science'
_journal_page_first              4703
_journal_page_last               4709
_journal_paper_doi               10.1039/d5sc00112a
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C5 H4 N O3 S, C5 H5 N O, C5 H6 N O'
_chemical_formula_sum            'C15 H15 N3 O5 S'
_chemical_formula_weight         349.36
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-10-25
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-10-25 deposited with the CCDC.	2025-02-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.8810(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.5972(5)
_cell_length_b                   7.0455(2)
_cell_length_c                   12.8268(3)
_cell_measurement_reflns_used    9931
_cell_measurement_temperature    303.00
_cell_measurement_theta_max      28.30
_cell_measurement_theta_min      3.11
_cell_volume                     1590.09(7)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      303.00
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29324
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         2.315
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6527
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0853 before and 0.0774 after correction.
The Ratio of minimum to maximum transmission is 0.8753.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         2795
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0404
_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/[σ²(Fo²)+(0.0343P)²+0.9257P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0983
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2385
_reflns_number_total             2795
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5sc00112a2.cif
_cod_data_source_block           x_CCDC1
_cod_depositor_comments
'Adding full bibliography for 1573849--1573850.cif.'
_cod_database_code               1573850
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H) groups
2.a Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.34845(3) 0.12184(8) 0.43635(4) 0.03868(17) Uani 1 1 d . . . . .
O002 O 0.34251(9) 0.1404(3) 0.54887(12) 0.0546(4) Uani 1 1 d . . . . .
O003 O 0.37622(9) -0.0618(2) 0.40476(14) 0.0577(5) Uani 1 1 d . . . . .
O004 O 0.27962(8) 0.1786(3) 0.38227(13) 0.0585(5) Uani 1 1 d . . . . .
N006 N 0.54935(9) 0.3830(3) 0.40543(14) 0.0403(4) Uani 1 1 d . . . . .
O007 O 0.96454(8) 0.3286(3) 0.17501(13) 0.0684(6) Uani 1 1 d . . . . .
N008 N 0.70858(11) 0.3430(3) 0.42057(16) 0.0469(5) Uani 1 1 d . . . . .
N009 N 1.18834(11) 0.3354(3) 0.10674(16) 0.0488(5) Uani 1 1 d . . . . .
C00A C 0.41913(11) 0.2870(3) 0.39841(15) 0.0336(4) Uani 1 1 d . . . . .
C00B C 0.49403(11) 0.2627(3) 0.43060(16) 0.0366(5) Uani 1 1 d . . . . .
C00C C 0.53082(13) 0.5332(3) 0.34741(17) 0.0458(5) Uani 1 1 d . . . . .
C00D C 0.40132(13) 0.4428(4) 0.33733(18) 0.0476(6) Uani 1 1 d . . . . .
C00E C 0.86174(11) 0.3337(3) 0.37753(17) 0.0410(5) Uani 1 1 d . . . . .
C00F C 0.73159(13) 0.3630(3) 0.32192(19) 0.0478(6) Uani 1 1 d . . . . .
C00G C 0.80642(12) 0.3598(3) 0.29819(19) 0.0450(5) Uani 1 1 d . . . . .
C00H C 0.83520(13) 0.3156(4) 0.47963(19) 0.0455(5) Uani 1 1 d . . . . .
C00I C 1.09317(13) 0.3437(4) 0.2324(2) 0.0515(6) Uani 1 1 d . . . . .
C00J C 1.06124(13) 0.3182(4) 0.05097(19) 0.0525(6) Uani 1 1 d . . . . .
C00K C 0.75942(13) 0.3197(4) 0.49855(19) 0.0486(6) Uani 1 1 d . . . . .
C00L C 1.03669(12) 0.3299(4) 0.15440(18) 0.0482(6) Uani 1 1 d . . . . .
C00M C 1.16760(13) 0.3445(4) 0.2061(2) 0.0537(6) Uani 1 1 d . . . . .
C00N C 0.45812(15) 0.5675(4) 0.3120(2) 0.0544(6) Uani 1 1 d . . . . .
C00O C 1.13602(13) 0.3228(4) 0.0299(2) 0.0512(6) Uani 1 1 d . . . . .
O4 O 0.93374(8) 0.3267(3) 0.35987(13) 0.0576(5) Uani 1 1 d . . . . .
H4 H 0.940743 0.332894 0.296906 0.086 Uiso 1 1 calc R U . . .
H00K H 0.7408(15) 0.307(4) 0.565(2) 0.062(7) Uiso 1 1 d . . . . .
H00B H 0.5094(14) 0.151(4) 0.4762(19) 0.057(7) Uiso 1 1 d . . . . .
H00D H 0.3507(15) 0.460(4) 0.3133(19) 0.058(7) Uiso 1 1 d . . . . .
H00C H 0.5725(14) 0.620(3) 0.3302(19) 0.054(7) Uiso 1 1 d . . . . .
H00I H 1.0793(15) 0.351(4) 0.300(2) 0.060(8) Uiso 1 1 d . . . . .
H009 H 1.2348(19) 0.337(4) 0.090(2) 0.078(9) Uiso 1 1 d . . . . .
H00N H 0.4458(14) 0.671(4) 0.275(2) 0.060(8) Uiso 1 1 d . . . . .
H00G H 0.8210(15) 0.371(4) 0.234(2) 0.060(8) Uiso 1 1 d . . . . .
H00J H 1.0253(17) 0.308(4) -0.002(2) 0.076(9) Uiso 1 1 d . . . . .
H00O H 1.1563(15) 0.318(4) -0.038(2) 0.067(8) Uiso 1 1 d . . . . .
H00H H 0.8676(14) 0.299(3) 0.532(2) 0.053(7) Uiso 1 1 d . . . . .
H00F H 0.6944(15) 0.383(4) 0.270(2) 0.061(7) Uiso 1 1 d . . . . .
H00M H 1.2079(18) 0.355(4) 0.253(2) 0.079(9) Uiso 1 1 d . . . . .
H008 H 0.6611(17) 0.347(4) 0.433(2) 0.066(8) Uiso 1 1 d . . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O002 S001 C00A 105.91(9) . . ?
O003 S001 O002 112.88(11) . . ?
O003 S001 C00A 105.60(9) . . ?
O004 S001 O002 112.30(10) . . ?
O004 S001 O003 113.50(11) . . ?
O004 S001 C00A 105.83(10) . . ?
C00C N006 C00B 117.82(19) . . ?
C00F N008 H008 118.7(19) . . ?
C00K N008 C00F 120.6(2) . . ?
C00K N008 H008 120.7(19) . . ?
C00M N009 C00O 120.7(2) . . ?
C00M N009 H009 122(2) . . ?
C00O N009 H009 118(2) . . ?
C00B C00A S001 120.26(16) . . ?
C00D C00A S001 121.47(16) . . ?
C00D C00A C00B 118.27(19) . . ?
N006 C00B C00A 122.9(2) . . ?
N006 C00B H00B 116.3(14) . . ?
C00A C00B H00B 120.8(14) . . ?
N006 C00C C00N 123.0(2) . . ?
N006 C00C H00C 116.3(14) . . ?
C00N C00C H00C 120.7(14) . . ?
C00A C00D H00D 119.4(16) . . ?
C00N C00D C00A 118.9(2) . . ?
C00N C00D H00D 121.7(15) . . ?
C00H C00E C00G 116.7(2) . . ?
O4 C00E C00G 123.2(2) . . ?
O4 C00E C00H 120.1(2) . . ?
N008 C00F C00G 121.2(2) . . ?
N008 C00F H00F 118.1(16) . . ?
C00G C00F H00F 120.7(16) . . ?
C00E C00G H00G 118.9(18) . . ?
C00F C00G C00E 120.2(2) . . ?
C00F C00G H00G 121.0(18) . . ?
C00E C00H H00H 120.1(16) . . ?
C00K C00H C00E 120.4(2) . . ?
C00K C00H H00H 119.5(16) . . ?
C00L C00I H00I 119.1(17) . . ?
C00M C00I C00L 119.9(2) . . ?
C00M C00I H00I 121.0(17) . . ?
C00L C00J H00J 118.8(18) . . ?
C00O C00J C00L 120.2(2) . . ?
C00O C00J H00J 121.0(18) . . ?
N008 C00K C00H 120.9(2) . . ?
N008 C00K H00K 117.4(16) . . ?
C00H C00K H00K 121.7(17) . . ?
O007 C00L C00I 122.6(2) . . ?
O007 C00L C00J 120.5(2) . . ?
C00I C00L C00J 116.9(2) . . ?
N009 C00M C00I 121.2(2) . . ?
N009 C00M H00M 114.3(19) . . ?
C00I C00M H00M 124.5(19) . . ?
C00C C00N C00D 119.1(2) . . ?
C00C C00N H00N 122.5(17) . . ?
C00D C00N H00N 118.4(17) . . ?
N009 C00O C00J 121.0(2) . . ?
N009 C00O H00O 114.4(16) . . ?
C00J C00O H00O 124.5(16) . . ?
C00E O4 H4 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 O002 1.4546(16) . ?
S001 O003 1.4434(17) . ?
S001 O004 1.4430(16) . ?
S001 C00A 1.777(2) . ?
N006 C00B 1.334(3) . ?
N006 C00C 1.331(3) . ?
O007 C00L 1.301(3) . ?
N008 C00F 1.342(3) . ?
N008 C00K 1.342(3) . ?
N008 H008 0.85(3) . ?
N009 C00M 1.332(3) . ?
N009 C00O 1.341(3) . ?
N009 H009 0.85(3) . ?
C00A C00B 1.386(3) . ?
C00A C00D 1.382(3) . ?
C00B H00B 1.01(3) . ?
C00C C00N 1.373(3) . ?
C00C H00C 0.98(3) . ?
C00D C00N 1.374(3) . ?
C00D H00D 0.95(3) . ?
C00E C00G 1.409(3) . ?
C00E C00H 1.403(3) . ?
C00E O4 1.291(3) . ?
C00F C00G 1.356(3) . ?
C00F H00F 0.94(3) . ?
C00G H00G 0.87(3) . ?
C00H C00K 1.359(3) . ?
C00H H00H 0.88(3) . ?
C00I C00L 1.402(3) . ?
C00I C00M 1.358(3) . ?
C00I H00I 0.90(3) . ?
C00J C00L 1.404(3) . ?
C00J C00O 1.348(3) . ?
C00J H00J 0.92(3) . ?
C00K H00K 0.93(3) . ?
C00M H00M 0.93(3) . ?
C00N H00N 0.89(3) . ?
C00O H00O 0.95(3) . ?
O4 H4 0.8200 . ?
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 C00A C00B N006 -179.33(16) . . . . ?
S001 C00A C00D C00N 178.87(18) . . . . ?
O002 S001 C00A C00B 65.82(19) . . . . ?
O002 S001 C00A C00D -113.64(19) . . . . ?
O003 S001 C00A C00B -54.14(19) . . . . ?
O003 S001 C00A C00D 126.40(19) . . . . ?
O004 S001 C00A C00B -174.77(17) . . . . ?
O004 S001 C00A C00D 5.8(2) . . . . ?
N006 C00C C00N C00D 0.3(4) . . . . ?
N008 C00F C00G C00E 0.5(4) . . . . ?
C00A C00D C00N C00C 0.4(4) . . . . ?
C00B N006 C00C C00N -0.7(3) . . . . ?
C00B C00A C00D C00N -0.6(3) . . . . ?
C00C N006 C00B C00A 0.5(3) . . . . ?
C00D C00A C00B N006 0.2(3) . . . . ?
C00E C00H C00K N008 -0.7(4) . . . . ?
C00F N008 C00K C00H -0.1(4) . . . . ?
C00G C00E C00H C00K 1.3(4) . . . . ?
C00H C00E C00G C00F -1.2(3) . . . . ?
C00K N008 C00F C00G 0.1(4) . . . . ?
C00L C00I C00M N009 1.1(4) . . . . ?
C00L C00J C00O N009 1.1(4) . . . . ?
C00M N009 C00O C00J -0.3(4) . . . . ?
C00M C00I C00L O007 -180.0(3) . . . . ?
C00M C00I C00L C00J -0.3(4) . . . . ?
C00O N009 C00M C00I -0.8(4) . . . . ?
C00O C00J C00L O007 178.9(3) . . . . ?
C00O C00J C00L C00I -0.8(4) . . . . ?
O4 C00E C00G C00F 179.0(2) . . . . ?
O4 C00E C00H C00K -178.9(2) . . . . ?
