#------------------------------------------------------------------------------
#$Date: 2025-08-19 20:55:00 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301808 $
#$URL: svn://www.crystallography.net/cod/cif/2/30/03/2300322.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2300322
loop_
_publ_author_name
'Eccles, Kevin S.'
'Stokes, Stephen P.'
'Daly, Carla A.'
'Barry, Nicola M.'
'McSweeney, Sharon P.'
'O'Neill, Damian J.'
'Kelly, Dawn M.'
'Jennings, W. Brian'
'Ní Dhubhghaill, O. M.'
'Moynihan, Humphrey A.'
'Maguire, Anita R.'
'Lawrence, Simon E.'
_publ_section_title
;
 Evaluation of the Bruker SMART X2S: crystallography for the
 nonspecialist?
;
_journal_coden_ASTM              JACGAR
_journal_coeditor_code           KK5074
_journal_issue                   1
_journal_name_full               'Journal of Applied Crystallography'
_journal_page_first              213
_journal_page_last               215
_journal_paper_doi               10.1107/S0021889810042561
_journal_volume                  44
_journal_year                    2011
_chemical_formula_moiety         'C13 H18 N2 O3 S'
_chemical_formula_sum            'C13 H18 N2 O3 S'
_chemical_formula_weight         282.35
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.379(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.8651(14)
_cell_length_b                   15.3291(14)
_cell_length_c                   7.1435(8)
_cell_measurement_reflns_used    3155
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      24.47
_cell_measurement_theta_min      2.66
_cell_volume                     1406.3(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker GIS'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker APEX2'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            13591
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.365
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2482
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.178
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0911P)²+0.2744P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1384
_reflns_number_gt                1862
_reflns_number_total             2482
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            kk5074.cif
_cod_data_source_block           Compound_7_X2S
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P12(1)/c1
_cod_database_code               2300322
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.33423(5) 0.08148(4) 0.13084(9) 0.0460(2) Uani d . 1 . .
O O1 0.37112(17) -0.00653(12) 0.1231(3) 0.0639(6) Uani d . 1 . .
O O2 0.28768(17) 0.11992(14) -0.0363(2) 0.0686(6) Uani d . 1 . .
O O3 0.82867(16) 0.21154(14) 0.4203(4) 0.0803(7) Uani d . 1 . .
N N1 0.69540(15) 0.30618(12) 0.3612(3) 0.0411(5) Uani d . 1 . .
H H1 0.6807 0.3609 0.3594 0.049 Uiso calc R 1 . .
N N2 0.24632(16) 0.08331(12) 0.2859(3) 0.0411(5) Uani d . 1 . .
C C1 0.8656(2) 0.3629(2) 0.4483(5) 0.0684(8) Uani d . 1 . .
H H1A 0.8820 0.3672 0.5809 0.103 Uiso calc R 1 . .
H H1B 0.8306 0.4151 0.4050 0.103 Uiso calc R 1 . .
H H1C 0.9287 0.3560 0.3845 0.103 Uiso calc R 1 . .
C C2 0.7967(2) 0.28618(18) 0.4089(4) 0.0495(6) Uani d . 1 . .
C C3 0.61164(18) 0.25016(14) 0.3148(3) 0.0353(5) Uani d . 1 . .
C C4 0.51545(18) 0.28786(14) 0.2662(3) 0.0382(5) Uani d . 1 . .
H H4 0.5083 0.3482 0.2690 0.046 Uiso calc R 1 . .
C C5 0.43120(18) 0.23700(15) 0.2145(3) 0.0401(6) Uani d . 1 . .
H H5 0.3673 0.2630 0.1825 0.048 Uiso calc R 1 . .
C C6 0.44078(19) 0.14622(14) 0.2096(3) 0.0390(6) Uani d . 1 . .
C C7 0.2776(2) 0.04740(16) 0.4723(3) 0.0470(6) Uani d . 1 . .
H H7A 0.3165 0.0909 0.5459 0.056 Uiso calc R 1 . .
H H7B 0.3222 -0.0029 0.4585 0.056 Uiso calc R 1 . .
C C8 0.1821(2) 0.02102(18) 0.5718(4) 0.0566(7) Uani d . 1 . .
H H8A 0.1481 -0.0274 0.5056 0.068 Uiso calc R 1 . .
H H8B 0.2029 0.0016 0.6977 0.068 Uiso calc R 1 . .
C C9 0.1067(2) 0.0956(2) 0.5822(5) 0.0712(9) Uani d . 1 . .
H H9A 0.1369 0.1405 0.6641 0.085 Uiso calc R 1 . .
H H9B 0.0434 0.0752 0.6352 0.085 Uiso calc R 1 . .
C C10 0.6206(2) 0.15966(15) 0.3122(4) 0.0465(6) Uani d . 1 . .
H H10 0.6842 0.1336 0.3459 0.056 Uiso calc R 1 . .
C C11 0.5362(2) 0.10888(16) 0.2602(4) 0.0470(6) Uani d . 1 . .
H H11 0.5431 0.0485 0.2589 0.056 Uiso calc R 1 . .
C C12 0.1775(2) 0.15985(18) 0.2943(4) 0.0583(7) Uani d . 1 . .
H H12A 0.1593 0.1809 0.1686 0.070 Uiso calc R 1 . .
H H12B 0.2131 0.2064 0.3643 0.070 Uiso calc R 1 . .
C C13 0.0804(2) 0.1340(2) 0.3889(6) 0.0774(10) Uani d . 1 . .
H H13A 0.0419 0.0914 0.3120 0.093 Uiso calc R 1 . .
H H13B 0.0364 0.1849 0.4007 0.093 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 S1 O1 . . 118.62(13) ?
O2 S1 N2 . . 106.68(12) ?
O1 S1 N2 . . 106.71(11) ?
O2 S1 C6 . . 108.34(11) ?
O1 S1 C6 . . 106.87(12) ?
N2 S1 C6 . . 109.39(10) ?
C2 N1 C3 . . 129.2(2) ?
C2 N1 H1 . . 115.4 ?
C3 N1 H1 . . 115.4 ?
C12 N2 C7 . . 113.2(2) ?
C12 N2 S1 . . 118.96(17) ?
C7 N2 S1 . . 116.37(16) ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O3 C2 N1 . . 122.9(3) ?
O3 C2 C1 . . 122.3(3) ?
N1 C2 C1 . . 114.8(2) ?
C4 C3 C10 . . 118.9(2) ?
C4 C3 N1 . . 117.68(19) ?
C10 C3 N1 . . 123.4(2) ?
C5 C4 C3 . . 120.6(2) ?
C5 C4 H4 . . 119.7 ?
C3 C4 H4 . . 119.7 ?
C4 C5 C6 . . 120.3(2) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C11 C6 C5 . . 118.9(2) ?
C11 C6 S1 . . 120.89(18) ?
C5 C6 S1 . . 120.13(19) ?
N2 C7 C8 . . 109.8(2) ?
N2 C7 H7A . . 109.7 ?
C8 C7 H7A . . 109.7 ?
N2 C7 H7B . . 109.7 ?
C8 C7 H7B . . 109.7 ?
H7A C7 H7B . . 108.2 ?
C9 C8 C7 . . 111.4(2) ?
C9 C8 H8A . . 109.4 ?
C7 C8 H8A . . 109.4 ?
C9 C8 H8B . . 109.4 ?
C7 C8 H8B . . 109.4 ?
H8A C8 H8B . . 108.0 ?
C8 C9 C13 . . 111.0(3) ?
C8 C9 H9A . . 109.4 ?
C13 C9 H9A . . 109.4 ?
C8 C9 H9B . . 109.4 ?
C13 C9 H9B . . 109.4 ?
H9A C9 H9B . . 108.0 ?
C11 C10 C3 . . 120.3(2) ?
C11 C10 H10 . . 119.8 ?
C3 C10 H10 . . 119.8 ?
C10 C11 C6 . . 120.9(2) ?
C10 C11 H11 . . 119.6 ?
C6 C11 H11 . . 119.6 ?
N2 C12 C13 . . 109.0(2) ?
N2 C12 H12A . . 109.9 ?
C13 C12 H12A . . 109.9 ?
N2 C12 H12B . . 109.9 ?
C13 C12 H12B . . 109.9 ?
H12A C12 H12B . . 108.3 ?
C12 C13 C9 . . 111.3(3) ?
C12 C13 H13A . . 109.4 ?
C9 C13 H13A . . 109.4 ?
C12 C13 H13B . . 109.4 ?
C9 C13 H13B . . 109.4 ?
H13A C13 H13B . . 108.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O2 . 1.431(2) ?
S1 O1 . 1.432(2) ?
S1 N2 . 1.629(2) ?
S1 C6 . 1.758(2) ?
O3 C2 . 1.217(3) ?
N1 C2 . 1.362(3) ?
N1 C3 . 1.402(3) ?
N1 H1 . 0.8600 ?
N2 C12 . 1.473(3) ?
N2 C7 . 1.474(3) ?
C1 C2 . 1.491(4) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C3 C4 . 1.391(3) ?
C3 C10 . 1.392(3) ?
C4 C5 . 1.368(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.398(3) ?
C5 H5 . 0.9300 ?
C6 C11 . 1.383(3) ?
C7 C8 . 1.510(4) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.504(4) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C13 . 1.521(5) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C11 . 1.369(4) ?
C10 H10 . 0.9300 ?
C11 H11 . 0.9300 ?
C12 C13 . 1.508(4) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
loop_
_cod_entry_issue_id
_cod_entry_issue_origin
_cod_entry_issue_severity
_cod_entry_issue_description
_cod_entry_issue_author
_cod_entry_issue_date
1 original note
;
 This entry describes a structure that was purposely solved automatically with
 minimal human intervention to investigate the capabilities of the Bruker SMART
 X2S benchtop crystallography instrument.
;
'Vaitkus, Antanas' 2025-01-27T16:15:51+02:00
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 72074
2 PubChem 79780
