#------------------------------------------------------------------------------
#$Date: 2022-02-04 00:57:29 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272500 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/96/7129661.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_7129661
loop_
_publ_author_name
'Miura, Tomoya'
'Moritani, Shunsuke'
'Shiratori, Yota'
'Murakami, Masahiro'
_publ_section_title
;
 1,2-Acyl migration with α-imino rhodium carbenoids leading to
 substituted 1-naphthols
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06349A
_journal_year                    2022
_chemical_formula_moiety         'C19 H17 N O3 S'
_chemical_formula_sum            'C19 H17 N O3 S'
_chemical_formula_weight         339.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2021-09-18 deposited with the CCDC.	2022-01-21 downloaded from the CCDC.
;
_cell_angle_alpha                81.981(8)
_cell_angle_beta                 89.271(9)
_cell_angle_gamma                88.832(8)
_cell_formula_units_Z            2
_cell_length_a                   6.478(2)
_cell_length_b                   8.078(3)
_cell_length_c                   15.574(5)
_cell_measurement_reflns_used    2854
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.00
_cell_volume                     806.8(5)
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b46'
_computing_data_collection
'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b46'
_computing_molecular_graphics    'CrystalStructure 4.2'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6488
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        27.480
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         3.028
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             356.00
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.67
_refine_diff_density_min         -0.72
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3545
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0966P)²+0.3480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1506
_refine_ls_wR_factor_ref         0.1554
_reflns_number_gt                2917
_reflns_number_total             3545
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d1cc06349a2.cif
_cod_data_source_block           2020_12_11_TM
_cod_database_code               7129661
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.22744(7) 0.26011(6) 0.16909(3) 0.01888(17) Uani 1 1 d . . .
O1 O 0.1549(2) 0.15088(19) 0.43405(9) 0.0262(3) Uani 1 1 d . . .
H1A H 0.1423 0.1683 0.3812 0.031 Uiso 1 1 calc R . .
O2 O 0.1065(2) 0.11781(17) 0.15886(9) 0.0255(3) Uani 1 1 d . . .
O3 O 0.4256(2) 0.27811(19) 0.12670(9) 0.0253(3) Uani 1 1 d . . .
N1 N 0.2536(3) 0.2563(2) 0.27554(10) 0.0203(4) Uani 1 1 d . . .
C1 C 0.4286(3) 0.3029(2) 0.30351(12) 0.0194(4) Uani 1 1 d . . .
H1 H 0.5284 0.3452 0.2634 0.023 Uiso 1 1 calc R . .
C2 C 0.4725(3) 0.2913(2) 0.39436(12) 0.0197(4) Uani 1 1 d . . .
C3 C 0.3341(3) 0.2100(2) 0.45574(12) 0.0204(4) Uani 1 1 d . . .
C4 C 0.3835(3) 0.1847(2) 0.54586(12) 0.0213(4) Uani 1 1 d . . .
C5 C 0.2457(4) 0.1027(3) 0.60853(13) 0.0266(5) Uani 1 1 d . . .
H5 H 0.1192 0.0666 0.5914 0.032 Uiso 1 1 calc R . .
C6 C 0.2987(4) 0.0766(3) 0.69436(14) 0.0303(5) Uani 1 1 d . . .
H6 H 0.2083 0.0226 0.7354 0.036 Uiso 1 1 calc R . .
C7 C 0.4901(4) 0.1317(3) 0.72028(14) 0.0323(5) Uani 1 1 d . . .
H7 H 0.5255 0.1133 0.7786 0.039 Uiso 1 1 calc R . .
C8 C 0.6247(4) 0.2120(3) 0.66079(14) 0.0304(5) Uani 1 1 d . . .
H8 H 0.7505 0.2474 0.6791 0.036 Uiso 1 1 calc R . .
C9 C 0.5746(3) 0.2419(3) 0.57148(12) 0.0236(4) Uani 1 1 d . . .
C10 C 0.7112(3) 0.3261(3) 0.50820(13) 0.0243(4) Uani 1 1 d . . .
H10 H 0.8357 0.3645 0.5260 0.029 Uiso 1 1 calc R . .
C11 C 0.6641(3) 0.3517(2) 0.42226(12) 0.0214(4) Uani 1 1 d . . .
C12 C 0.8088(3) 0.4449(3) 0.35687(13) 0.0266(5) Uani 1 1 d . . .
H12A H 0.9399 0.3871 0.3584 0.032 Uiso 1 1 calc R . .
H12B H 0.8271 0.5559 0.3707 0.032 Uiso 1 1 calc R . .
H12C H 0.7516 0.4512 0.2999 0.032 Uiso 1 1 calc R . .
C13 C 0.0771(3) 0.4419(2) 0.13891(11) 0.0186(4) Uani 1 1 d . . .
C14 C -0.1210(3) 0.4295(2) 0.10893(12) 0.0215(4) Uani 1 1 d . . .
H14 H -0.1774 0.3255 0.1062 0.026 Uiso 1 1 calc R . .
C15 C -0.2348(3) 0.5757(3) 0.08294(13) 0.0245(4) Uani 1 1 d . . .
H15 H -0.3679 0.5686 0.0622 0.029 Uiso 1 1 calc R . .
C16 C -0.1530(3) 0.7318(3) 0.08741(12) 0.0239(4) Uani 1 1 d . . .
C17 C 0.0470(4) 0.7399(3) 0.11904(14) 0.0286(5) Uani 1 1 d . . .
H17 H 0.1027 0.8437 0.1232 0.034 Uiso 1 1 calc R . .
C18 C 0.1631(3) 0.5967(3) 0.14423(14) 0.0251(4) Uani 1 1 d . . .
H18 H 0.2967 0.6034 0.1644 0.030 Uiso 1 1 calc R . .
C19 C -0.2761(4) 0.8891(3) 0.05786(14) 0.0329(5) Uani 1 1 d . . .
H19A H -0.4013 0.8895 0.0914 0.039 Uiso 1 1 calc R . .
H19B H -0.3090 0.8934 -0.0023 0.039 Uiso 1 1 calc R . .
H19C H -0.1963 0.9847 0.0657 0.039 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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(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 S1 O3 118.87(9) . . ?
O2 S1 N1 105.74(9) . . ?
O3 S1 N1 110.04(9) . . ?
O2 S1 C13 108.56(9) . . ?
O3 S1 C13 109.33(9) . . ?
N1 S1 C13 103.13(8) . . ?
C3 O1 H1A 109.5 . . ?
C1 N1 S1 117.90(14) . . ?
N1 C1 C2 122.14(18) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C3 C2 C1 119.75(18) . . ?
C3 C2 C11 119.94(17) . . ?
C1 C2 C11 120.16(18) . . ?
O1 C3 C2 122.82(18) . . ?
O1 C3 C4 116.65(18) . . ?
C2 C3 C4 120.52(18) . . ?
C9 C4 C5 120.31(18) . . ?
C9 C4 C3 118.50(18) . . ?
C5 C4 C3 121.19(19) . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 119.9(2) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 120.9(2) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 120.8(2) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C4 C9 C8 118.07(19) . . ?
C4 C9 C10 119.97(18) . . ?
C8 C9 C10 122.0(2) . . ?
C11 C10 C9 121.76(19) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C2 119.29(18) . . ?
C10 C11 C12 120.73(19) . . ?
C2 C11 C12 119.98(17) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 121.30(18) . . ?
C14 C13 S1 119.93(15) . . ?
C18 C13 S1 118.76(15) . . ?
C13 C14 C15 118.81(19) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C16 C15 C14 121.2(2) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 118.60(18) . . ?
C15 C16 C19 120.7(2) . . ?
C17 C16 C19 120.7(2) . . ?
C18 C17 C16 121.14(19) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C13 118.97(19) . . ?
C17 C18 H18 120.5 . . ?
C13 C18 H18 120.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
S1 O2 1.4324(15) . ?
S1 O3 1.4369(16) . ?
S1 N1 1.6646(17) . ?
S1 C13 1.757(2) . ?
O1 C3 1.330(3) . ?
O1 H1A 0.8200 . ?
N1 C1 1.301(3) . ?
C1 C2 1.437(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.406(3) . ?
C2 C11 1.437(3) . ?
C3 C4 1.429(3) . ?
C4 C9 1.411(3) . ?
C4 C5 1.418(3) . ?
C5 C6 1.371(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.409(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.369(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.419(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.426(3) . ?
C10 C11 1.363(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.508(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.381(3) . ?
C13 C18 1.393(3) . ?
C14 C15 1.393(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.389(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.398(3) . ?
C16 C19 1.506(3) . ?
C17 C18 1.380(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1A N1 . . . 2.574(2) 0.820 1.843 147.6 no
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
O2 S1 N1 C1 143.36(15) . . . . ?
O3 S1 N1 C1 13.81(17) . . . . ?
C13 S1 N1 C1 -102.73(16) . . . . ?
S1 N1 C1 C2 -174.84(14) . . . . ?
N1 C1 C2 C3 7.4(3) . . . . ?
N1 C1 C2 C11 -177.04(17) . . . . ?
C1 C2 C3 O1 -4.2(3) . . . . ?
C11 C2 C3 O1 -179.80(17) . . . . ?
C1 C2 C3 C4 174.68(17) . . . . ?
C11 C2 C3 C4 -0.9(3) . . . . ?
O1 C3 C4 C9 178.47(17) . . . . ?
C2 C3 C4 C9 -0.5(3) . . . . ?
O1 C3 C4 C5 -0.9(3) . . . . ?
C2 C3 C4 C5 -179.88(18) . . . . ?
C9 C4 C5 C6 -0.8(3) . . . . ?
C3 C4 C5 C6 178.52(19) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C5 C4 C9 C8 1.1(3) . . . . ?
C3 C4 C9 C8 -178.25(18) . . . . ?
C5 C4 C9 C10 -179.22(18) . . . . ?
C3 C4 C9 C10 1.4(3) . . . . ?
C7 C8 C9 C4 -0.7(3) . . . . ?
C7 C8 C9 C10 179.6(2) . . . . ?
C4 C9 C10 C11 -0.9(3) . . . . ?
C8 C9 C10 C11 178.73(19) . . . . ?
C9 C10 C11 C2 -0.5(3) . . . . ?
C9 C10 C11 C12 178.46(18) . . . . ?
C3 C2 C11 C10 1.4(3) . . . . ?
C1 C2 C11 C10 -174.15(17) . . . . ?
C3 C2 C11 C12 -177.57(17) . . . . ?
C1 C2 C11 C12 6.9(3) . . . . ?
O2 S1 C13 C14 -1.74(18) . . . . ?
O3 S1 C13 C14 129.37(16) . . . . ?
N1 S1 C13 C14 -113.59(16) . . . . ?
O2 S1 C13 C18 179.55(15) . . . . ?
O3 S1 C13 C18 -49.34(18) . . . . ?
N1 S1 C13 C18 67.70(17) . . . . ?
C18 C13 C14 C15 0.6(3) . . . . ?
S1 C13 C14 C15 -178.07(14) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C14 C15 C16 C19 179.06(18) . . . . ?
C15 C16 C17 C18 1.0(3) . . . . ?
C19 C16 C17 C18 -178.34(19) . . . . ?
C16 C17 C18 C13 -0.9(3) . . . . ?
C14 C13 C18 C17 0.1(3) . . . . ?
S1 C13 C18 C17 178.79(16) . . . . ?
