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#$Date: 2022-08-18 00:56:30 +0300 (Thu, 18 Aug 2022) $
#$Revision: 277282 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/05/7130541.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_7130541
loop_
_publ_author_name
'Soltau, Carl P.'
'Brown, Zachary'
'Brock, Aidan J.'
'Martyn, Alexander P.'
'Blinco, James P.'
'Miljevic, Branka'
'McMurtrie, John C.'
'Bottle, Steven E.'
_publ_section_title
;
 Reactions of Sulfoxides with Reactive Oxygen Species to Reveal the
 Radical Chemistry of Pollution-Derived Particulate Matter
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04024G
_journal_year                    2022
_chemical_formula_moiety         'C12 H13 N O2'
_chemical_formula_sum            'C12 H13 N O2'
_chemical_formula_weight         203.23
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-10-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2022-06-16 deposited with the CCDC.	2022-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.86(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.9850(16)
_cell_length_b                   6.6850(13)
_cell_length_c                   9.4400(19)
_cell_measurement_reflns_used    6912
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.328
_cell_measurement_theta_min      2.197
_cell_volume                     494.88(18)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.782
_diffrn_measurement_device_type  'Eiger 2 9M'
_diffrn_measurement_method       'Phi scans'
_diffrn_radiation_monochromator  'Silicon double crystal'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.7108
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.782
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6912
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.782
_diffrn_reflns_theta_full        25.244
_diffrn_reflns_theta_max         29.328
_diffrn_reflns_theta_min         2.197
_diffrn_source                   'MX1 Beamline Australian Synchrotron'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       block
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.017(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0372
_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)+(0.0660P)²+0.0938P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1126
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1093
_reflns_number_total             1144
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc04024g2.cif
_cod_data_source_block           p21onm_a
_cod_database_code               7130541
_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.
;
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.991
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H11A(0.5) H11B(0.5) H11C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C3(H3), C4(H4)
3.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C10(H10A,H10B,H10C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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
O2 O 0.26101(12) 0.250000 0.56627(11) 0.0246(3) Uani 1 2 d S T P . .
O1 O 0.48415(13) 0.250000 0.38405(10) 0.0256(3) Uani 1 2 d S T P . .
N1 N 0.70595(14) 0.250000 0.57208(11) 0.0168(3) Uani 1 2 d S T P . .
C8 C 0.53887(16) 0.250000 0.51521(13) 0.0173(3) Uani 1 2 d S T P . .
C1 C 0.48024(16) 0.250000 0.77380(13) 0.0172(3) Uani 1 2 d S T P . .
C9 C 0.41236(16) 0.250000 0.61820(14) 0.0178(3) Uani 1 2 d S T P . .
C7 C 0.78592(15) 0.250000 0.72695(13) 0.0162(3) Uani 1 2 d S T P . .
C6 C 0.65533(16) 0.250000 0.82494(13) 0.0167(3) Uani 1 2 d S T P . .
C5 C 0.71293(18) 0.250000 0.97475(14) 0.0211(3) Uani 1 2 d S T P . .
H5 H 0.831957 0.250000 1.012446 0.025 Uiso 1 2 calc R U P . .
C11 C 0.81994(16) 0.250000 0.46645(14) 0.0207(3) Uani 1 2 d S T P . .
H11A H 0.789387 0.139114 0.398597 0.031 Uiso 0.5 1 calc R U P A -1
H11B H 0.938203 0.233992 0.516877 0.031 Uiso 0.5 1 calc R U P A -1
H11C H 0.808161 0.376894 0.413519 0.031 Uiso 0.5 1 calc R U P A -1
C2 C 0.36488(18) 0.250000 0.86955(16) 0.0216(3) Uani 1 2 d S T P . .
H2 H 0.245630 0.250000 0.832840 0.026 Uiso 1 2 calc R U P . .
C3 C 0.42429(19) 0.250000 1.01644(15) 0.0244(3) Uani 1 2 d S T P . .
H3 H 0.346520 0.250000 1.081202 0.029 Uiso 1 2 calc R U P . .
C10 C 0.89470(11) 0.44142(14) 0.75671(10) 0.0218(3) Uani 1 1 d . . . . .
H10A H 0.984707 0.439254 0.699056 0.033 Uiso 1 1 calc R U . . .
H10B H 0.946411 0.447660 0.859362 0.033 Uiso 1 1 calc R U . . .
H10C H 0.822104 0.558973 0.730638 0.033 Uiso 1 1 calc R U . . .
C4 C 0.5985(2) 0.250000 1.06878(14) 0.0251(3) Uani 1 2 d S T P . .
H4 H 0.640092 0.250000 1.169930 0.030 Uiso 1 2 calc R U P . .
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'
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
C8 N1 C7 127.34(10) . . ?
C8 N1 C11 115.12(10) . . ?
C11 N1 C7 117.54(10) . . ?
O1 C8 N1 122.66(11) . . ?
O1 C8 C9 119.16(12) . . ?
N1 C8 C9 118.18(11) . . ?
C6 C1 C9 120.35(11) . . ?
C6 C1 C2 120.94(13) . . ?
C2 C1 C9 118.70(13) . . ?
O2 C9 C8 118.01(12) . . ?
O2 C9 C1 123.75(12) . . ?
C1 C9 C8 118.25(12) . . ?
N1 C7 C6 112.55(10) . . ?
N1 C7 C10 107.64(6) . . ?
N1 C7 C10 107.64(6) . 4_565 ?
C6 C7 C10 108.47(6) . 4_565 ?
C6 C7 C10 108.47(6) . . ?
C10 C7 C10 112.12(10) . 4_565 ?
C1 C6 C7 123.33(12) . . ?
C1 C6 C5 117.87(12) . . ?
C5 C6 C7 118.81(12) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 120.96(13) . . ?
C4 C5 H5 119.5 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.23(14) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.39(12) . . ?
C4 C3 H3 120.3 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.61(13) . . ?
C3 C4 H4 119.7 . . ?
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
O2 C9 1.2156(17) . ?
O1 C8 1.2328(16) . ?
N1 C8 1.3410(17) . ?
N1 C7 1.4810(16) . ?
N1 C11 1.4713(15) . ?
C8 C9 1.5283(17) . ?
C1 C9 1.4668(19) . ?
C1 C6 1.3904(19) . ?
C1 C2 1.4068(18) . ?
C7 C6 1.5187(16) . ?
C7 C10 1.5424(11) 4_565 ?
C7 C10 1.5424(11) . ?
C6 C5 1.4023(18) . ?
C5 H5 0.9500 . ?
C5 C4 1.3885(19) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C2 H2 0.9500 . ?
C2 C3 1.378(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C4 H4 0.9500 . ?
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
O1 C8 C9 O2 0.000(0) . . . . ?
O1 C8 C9 C1 180.000(0) . . . . ?
N1 C8 C9 O2 180.000(0) . . . . ?
N1 C8 C9 C1 0.000(0) . . . . ?
N1 C7 C6 C1 0.000(1) . . . . ?
N1 C7 C6 C5 180.000(0) . . . . ?
C8 N1 C7 C6 0.000(0) . . . . ?
C8 N1 C7 C10 -119.47(6) . . . . ?
C8 N1 C7 C10 119.47(6) . . . 4_565 ?
C1 C6 C5 C4 0.000(1) . . . . ?
C1 C2 C3 C4 0.000(1) . . . . ?
C9 C1 C6 C7 0.000(1) . . . . ?
C9 C1 C6 C5 180.000(1) . . . . ?
C9 C1 C2 C3 180.000(1) . . . . ?
C7 N1 C8 O1 180.000(0) . . . . ?
C7 N1 C8 C9 0.000(0) . . . . ?
C7 C6 C5 C4 180.000(1) . . . . ?
C6 C1 C9 O2 180.000(0) . . . . ?
C6 C1 C9 C8 0.000(1) . . . . ?
C6 C1 C2 C3 0.000(1) . . . . ?
C6 C5 C4 C3 0.000(1) . . . . ?
C11 N1 C8 O1 0.000(0) . . . . ?
C11 N1 C8 C9 180.000(0) . . . . ?
C11 N1 C7 C6 180.000(0) . . . . ?
C11 N1 C7 C10 -60.53(6) . . . 4_565 ?
C11 N1 C7 C10 60.53(6) . . . . ?
C2 C1 C9 O2 0.000(1) . . . . ?
C2 C1 C9 C8 180.000(0) . . . . ?
C2 C1 C6 C7 180.000(0) . . . . ?
C2 C1 C6 C5 0.000(1) . . . . ?
C2 C3 C4 C5 0.000(1) . . . . ?
C10 C7 C6 C1 118.99(7) . . . . ?
C10 C7 C6 C1 -118.99(7) 4_565 . . . ?
C10 C7 C6 C5 61.01(7) 4_565 . . . ?
C10 C7 C6 C5 -61.01(7) . . . . ?
