#------------------------------------------------------------------------------
#$Date: 2022-02-08 00:52:02 +0200 (Tue, 08 Feb 2022) $
#$Revision: 272839 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/96/7129668.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_7129668
loop_
_publ_author_name
'Zhao, Yue'
'Yu, Congjun'
'Liang, Wenjing'
'Atodiresei, Iuliana L.'
'Patureau, Frederic W.'
_publ_section_title
;
 TEMPO-mediated late stage photochemical hydroxylation of biaryl sulfonium
 salts
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC07057F
_journal_year                    2022
_chemical_formula_sum            'C22 H23 N O3'
_chemical_formula_weight         349.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-10-29 deposited with the CCDC.	2022-01-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.943(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2069(3)
_cell_length_b                   26.8100(11)
_cell_length_c                   8.7494(4)
_cell_measurement_reflns_used    5985
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.50
_cell_measurement_theta_min      2.54
_cell_volume                     1851.06(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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  0.0364
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            29640
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.700
_diffrn_reflns_theta_min         1.519
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.761
_exptl_absorpt_correction_T_min  0.6788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.539
_exptl_crystal_size_mid          0.460
_exptl_crystal_size_min          0.153
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         5740
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0507
_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)+(0.0672P)²+0.3135P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1491
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3827
_reflns_number_total             5740
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc07057f2.cif
_cod_data_source_block           mo_ia0165_0m_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7129668
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O1 O 0.59596(15) 0.37208(4) 0.94695(15) 0.0688(3) Uani 1 1 d . . . . .
N1 N 0.03166(13) 0.33851(4) 0.46465(13) 0.0412(2) Uani 1 1 d . . . . .
C1 C 0.56623(17) 0.41195(5) 0.88161(17) 0.0441(3) Uani 1 1 d . . . . .
O2 O 0.05187(11) 0.38938(3) 0.41686(11) 0.0439(2) Uani 1 1 d . . . . .
C2 C 0.42817(15) 0.42391(5) 0.73517(15) 0.0383(3) Uani 1 1 d . . . . .
O3 O -0.2564(2) 0.22178(6) 0.3362(3) 0.1184(7) Uani 1 1 d . . . . .
C3 C 0.30200(16) 0.39303(5) 0.64777(15) 0.0403(3) Uani 1 1 d . . . . .
H3 H 0.295846 0.359604 0.674094 0.048 Uiso 1 1 calc R U . . .
C4 C 0.18489(15) 0.41425(5) 0.51883(15) 0.0379(3) Uani 1 1 d . . . . .
C5 C 0.19497(17) 0.46423(5) 0.48060(16) 0.0439(3) Uani 1 1 d . . . . .
H5 H 0.114784 0.477581 0.393656 0.053 Uiso 1 1 calc R U . . .
C6 C 0.32262(18) 0.49446(5) 0.57002(17) 0.0462(3) Uani 1 1 d . . . . .
H6 H 0.329096 0.527862 0.543610 0.055 Uiso 1 1 calc R U . . .
C7 C 0.43963(15) 0.47418(5) 0.69860(15) 0.0389(3) Uani 1 1 d . . . . .
C8 C 0.58246(15) 0.49673(5) 0.82008(15) 0.0401(3) Uani 1 1 d . . . . .
C9 C 0.64111(19) 0.54510(6) 0.84099(18) 0.0503(3) Uani 1 1 d . . . . .
H9 H 0.592127 0.569869 0.768464 0.060 Uiso 1 1 calc R U . . .
C10 C 0.7754(2) 0.55604(6) 0.97315(19) 0.0550(4) Uani 1 1 d . . . . .
H10 H 0.815567 0.588595 0.989367 0.066 Uiso 1 1 calc R U . . .
C11 C 0.84930(19) 0.51969(6) 1.07979(19) 0.0553(4) Uani 1 1 d . . . . .
H11 H 0.939341 0.527895 1.166801 0.066 Uiso 1 1 calc R U . . .
C12 C 0.79191(18) 0.47094(6) 1.05986(18) 0.0512(3) Uani 1 1 d . . . . .
H12 H 0.841973 0.446245 1.132185 0.061 Uiso 1 1 calc R U . . .
C13 C 0.65831(16) 0.46011(5) 0.92957(16) 0.0419(3) Uani 1 1 d . . . . .
C14 C 0.06139(18) 0.30639(5) 0.33564(18) 0.0522(4) Uani 1 1 d . . . . .
C15 C 0.0240(2) 0.25274(6) 0.3768(3) 0.0735(5) Uani 1 1 d . . . . .
H15A H 0.026579 0.230954 0.288937 0.088 Uiso 1 1 calc R U . . .
H15B H 0.111687 0.241796 0.469456 0.088 Uiso 1 1 calc R U . . .
C16 C -0.1435(2) 0.24851(6) 0.4094(3) 0.0760(6) Uani 1 1 d . . . . .
C17 C -0.1607(2) 0.28227(7) 0.5399(2) 0.0720(5) Uani 1 1 d . . . . .
H17A H -0.078035 0.272913 0.638118 0.086 Uiso 1 1 calc R U . . .
H17B H -0.272650 0.278312 0.555129 0.086 Uiso 1 1 calc R U . . .
C18 C -0.13387(18) 0.33713(6) 0.50238(18) 0.0500(3) Uani 1 1 d . . . . .
C19 C 0.2496(2) 0.31073(8) 0.3463(3) 0.0760(6) Uani 1 1 d . . . . .
H19A H 0.277960 0.287272 0.274724 0.114 Uiso 1 1 calc R U . . .
H19B H 0.315305 0.303706 0.452967 0.114 Uiso 1 1 calc R U . . .
H19C H 0.273788 0.343934 0.317743 0.114 Uiso 1 1 calc R U . . .
C20 C -0.0410(2) 0.31945(7) 0.1667(2) 0.0699(5) Uani 1 1 d . . . . .
H20A H 0.000416 0.300484 0.092118 0.105 Uiso 1 1 calc R U . . .
H20B H -0.029478 0.354406 0.148265 0.105 Uiso 1 1 calc R U . . .
H20C H -0.158209 0.311672 0.153525 0.105 Uiso 1 1 calc R U . . .
C21 C -0.1139(3) 0.36814(9) 0.6520(2) 0.0745(5) Uani 1 1 d . . . . .
H21A H -0.100329 0.402619 0.628550 0.112 Uiso 1 1 calc R U . . .
H21B H -0.015908 0.357023 0.732678 0.112 Uiso 1 1 calc R U . . .
H21C H -0.212832 0.364350 0.689323 0.112 Uiso 1 1 calc R U . . .
C22 C -0.28721(19) 0.35611(7) 0.3722(2) 0.0640(4) Uani 1 1 d . . . . .
H22A H -0.258926 0.387103 0.330758 0.096 Uiso 1 1 calc R U . . .
H22B H -0.380993 0.361148 0.416173 0.096 Uiso 1 1 calc R U . . .
H22C H -0.317683 0.331973 0.288086 0.096 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 0.0033 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
O2 N1 C18 105.78(10) . . ?
O2 N1 C14 105.63(10) . . ?
C18 N1 C14 120.25(11) . . ?
O1 C1 C2 127.19(13) . . ?
O1 C1 C13 127.69(13) . . ?
C2 C1 C13 105.12(11) . . ?
C4 O2 N1 113.69(9) . . ?
C3 C2 C7 122.68(12) . . ?
C3 C2 C1 128.54(12) . . ?
C7 C2 C1 108.74(11) . . ?
C2 C3 C4 116.80(12) . . ?
O2 C4 C3 125.24(11) . . ?
O2 C4 C5 113.58(11) . . ?
C3 C4 C5 121.18(11) . . ?
C6 C5 C4 120.97(12) . . ?
C7 C6 C5 118.76(12) . . ?
C6 C7 C2 119.61(11) . . ?
C6 C7 C8 131.64(12) . . ?
C2 C7 C8 108.69(11) . . ?
C9 C8 C13 119.87(12) . . ?
C9 C8 C7 131.26(13) . . ?
C13 C8 C7 108.82(11) . . ?
C8 C9 C10 118.46(14) . . ?
C11 C10 C9 121.15(14) . . ?
C10 C11 C12 120.94(14) . . ?
C13 C12 C11 117.98(14) . . ?
C12 C13 C8 121.60(13) . . ?
C12 C13 C1 129.74(13) . . ?
C8 C13 C1 108.62(11) . . ?
N1 C14 C19 106.44(12) . . ?
N1 C14 C20 116.05(12) . . ?
C19 C14 C20 108.66(16) . . ?
N1 C14 C15 106.20(14) . . ?
C19 C14 C15 108.75(14) . . ?
C20 C14 C15 110.48(14) . . ?
C16 C15 C14 111.87(14) . . ?
O3 C16 C15 124.1(2) . . ?
O3 C16 C17 123.1(2) . . ?
C15 C16 C17 112.84(14) . . ?
C16 C17 C18 111.57(15) . . ?
N1 C18 C21 106.80(12) . . ?
N1 C18 C22 116.16(13) . . ?
C21 C18 C22 109.29(15) . . ?
N1 C18 C17 105.36(13) . . ?
C21 C18 C17 109.10(15) . . ?
C22 C18 C17 109.88(13) . . ?
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
O1 C1 1.2050(17) . ?
N1 O2 1.4494(13) . ?
N1 C18 1.4840(19) . ?
N1 C14 1.4921(19) . ?
C1 C2 1.4936(18) . ?
C1 C13 1.4968(19) . ?
O2 C4 1.3774(14) . ?
C2 C3 1.3811(17) . ?
C2 C7 1.3944(17) . ?
O3 C16 1.207(2) . ?
C3 C4 1.3874(17) . ?
C4 C5 1.3890(18) . ?
C5 C6 1.3842(18) . ?
C6 C7 1.3747(18) . ?
C7 C8 1.4781(17) . ?
C8 C9 1.3780(19) . ?
C8 C13 1.3933(19) . ?
C9 C10 1.392(2) . ?
C10 C11 1.370(2) . ?
C11 C12 1.384(2) . ?
C12 C13 1.3782(19) . ?
C14 C19 1.526(2) . ?
C14 C20 1.527(2) . ?
C14 C15 1.534(2) . ?
C15 C16 1.483(3) . ?
C16 C17 1.493(3) . ?
C17 C18 1.536(2) . ?
C18 C21 1.521(2) . ?
C18 C22 1.534(2) . ?
