#------------------------------------------------------------------------------
#$Date: 2020-11-22 00:30:35 +0200 (Sun, 22 Nov 2020) $
#$Revision: 259215 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/82/4518260.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_4518260
loop_
_publ_author_name
'Apolinar, Omar'
'Tran, Van T.'
'Kim, Nana'
'Schmidt, Michael A.'
'Derosa, Joseph'
'Engle, Keary M.'
_publ_section_title
;
 Sulfonamide Directivity Enables Ni-Catalyzed 1,2-Diarylation of Diverse
 Alkenyl Amines
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              14234
_journal_page_last               14239
_journal_paper_doi               10.1021/acscatal.0c03857
_journal_year                    2020
_chemical_formula_moiety         'C24 H24 F3 N O2 S'
_chemical_formula_sum            'C24 H24 F3 N O2 S'
_chemical_formula_weight         447.50
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-17
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.9000(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6732(7)
_cell_length_b                   7.8057(3)
_cell_length_c                   16.9323(7)
_cell_measurement_reflns_used    4200
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.67
_cell_measurement_theta_min      2.48
_cell_volume                     2139.14(15)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12263
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.683
_diffrn_reflns_theta_min         2.889
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6625
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0419 before and 0.0390 after correction. The Ratio of minimum to maximum transmission is 0.8889. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4067
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0374P)²+1.0071P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0903
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3282
_reflns_number_total             4067
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c03857_si_002.cif
_cod_data_source_block           engle225_a
_cod_database_code               4518260
_shelx_shelxl_version_number     2017/1
_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   0.984
_shelx_estimated_absorpt_t_min   0.961
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C20(H20), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
S1 S 0.44745(2) 0.76259(5) 0.51949(2) 0.01325(12) Uani 1 1 d . . . . .
F1 F 0.61442(7) 0.72303(16) 0.91973(6) 0.0334(3) Uani 1 1 d . . . . .
O1 O 0.51675(7) 0.70774(15) 0.48944(7) 0.0175(3) Uani 1 1 d . . . . .
N1 N 0.38127(8) 0.60699(19) 0.49958(8) 0.0136(3) Uani 1 1 d . . . . .
H1 H 0.4048(11) 0.514(3) 0.5075(10) 0.016 Uiso 1 1 d R . . . .
C1 C 0.53524(11) 0.7569(2) 0.88563(11) 0.0226(4) Uani 1 1 d . . . . .
F2 F 0.51700(8) 0.90071(16) 0.92032(6) 0.0403(3) Uani 1 1 d . . . . .
O2 O 0.40453(7) 0.91726(15) 0.49033(7) 0.0185(3) Uani 1 1 d . . . . .
C2 C 0.51756(10) 0.7696(2) 0.79472(10) 0.0166(4) Uani 1 1 d . . . . .
F3 F 0.49140(8) 0.63210(17) 0.90962(7) 0.0441(4) Uani 1 1 d . . . . .
C3 C 0.56442(10) 0.6737(2) 0.75295(10) 0.0189(4) Uani 1 1 d . . . . .
H3 H 0.609555 0.607028 0.782090 0.023 Uiso 1 1 calc R . . . .
C4 C 0.54495(10) 0.6760(2) 0.66870(10) 0.0179(4) Uani 1 1 d . . . . .
H4 H 0.576292 0.610294 0.639616 0.022 Uiso 1 1 calc R . . . .
C5 C 0.47915(10) 0.7754(2) 0.62715(10) 0.0140(4) Uani 1 1 d . . . . .
C6 C 0.43332(10) 0.8748(2) 0.66841(10) 0.0185(4) Uani 1 1 d . . . . .
H6 H 0.389373 0.944566 0.639291 0.022 Uiso 1 1 calc R . . . .
C7 C 0.45277(10) 0.8707(2) 0.75294(10) 0.0200(4) Uani 1 1 d . . . . .
H7 H 0.421719 0.937064 0.782073 0.024 Uiso 1 1 calc R . . . .
C8 C 0.30311(9) 0.6214(2) 0.52566(10) 0.0149(4) Uani 1 1 d . . . . .
H8A H 0.276563 0.732791 0.507569 0.018 Uiso 1 1 calc R . . . .
H8B H 0.314767 0.617081 0.585783 0.018 Uiso 1 1 calc R . . . .
C9 C 0.24508(10) 0.4767(2) 0.48975(10) 0.0153(4) Uani 1 1 d . . . . .
H9A H 0.235315 0.481825 0.429776 0.018 Uiso 1 1 calc R . . . .
H9B H 0.191381 0.496925 0.503442 0.018 Uiso 1 1 calc R . . . .
C10 C 0.27425(10) 0.2942(2) 0.51755(9) 0.0137(4) Uani 1 1 d . . . . .
H10 H 0.326399 0.272183 0.499882 0.016 Uiso 1 1 calc R . . . .
C11 C 0.20935(10) 0.1631(2) 0.47358(10) 0.0169(4) Uani 1 1 d . . . . .
H11A H 0.228369 0.046127 0.491456 0.020 Uiso 1 1 calc R . . . .
H11B H 0.156653 0.183613 0.489262 0.020 Uiso 1 1 calc R . . . .
C12 C 0.19440(10) 0.1742(2) 0.38176(10) 0.0157(4) Uani 1 1 d . . . . .
C13 C 0.25255(10) 0.1088(2) 0.34299(10) 0.0176(4) Uani 1 1 d . . . . .
H13 H 0.300722 0.053898 0.374077 0.021 Uiso 1 1 calc R . . . .
C14 C 0.24064(11) 0.1231(2) 0.25891(10) 0.0203(4) Uani 1 1 d . . . . .
H14 H 0.280349 0.076466 0.233021 0.024 Uiso 1 1 calc R . . . .
C15 C 0.17155(11) 0.2046(2) 0.21299(10) 0.0206(4) Uani 1 1 d . . . . .
H15 H 0.164106 0.215888 0.155813 0.025 Uiso 1 1 calc R . . . .
C16 C 0.11309(11) 0.2700(2) 0.25092(11) 0.0213(4) Uani 1 1 d . . . . .
H16 H 0.065248 0.325633 0.219611 0.026 Uiso 1 1 calc R . . . .
C17 C 0.12431(10) 0.2544(2) 0.33440(11) 0.0197(4) Uani 1 1 d . . . . .
H17 H 0.083734 0.298866 0.359775 0.024 Uiso 1 1 calc R . . . .
C18 C 0.29438(10) 0.2794(2) 0.60973(10) 0.0140(4) Uani 1 1 d . . . . .
C19 C 0.23586(10) 0.2339(3) 0.65266(10) 0.0218(4) Uani 1 1 d . . . . .
H19 H 0.181231 0.206411 0.623596 0.026 Uiso 1 1 calc R . . . .
C20 C 0.25605(11) 0.2280(3) 0.73707(11) 0.0238(4) Uani 1 1 d . . . . .
H20 H 0.215421 0.192869 0.764559 0.029 Uiso 1 1 calc R . . . .
C21 C 0.33445(10) 0.2726(2) 0.78230(10) 0.0179(4) Uani 1 1 d . . . . .
C22 C 0.39250(10) 0.3190(2) 0.73985(10) 0.0177(4) Uani 1 1 d . . . . .
H22 H 0.446452 0.350935 0.769104 0.021 Uiso 1 1 calc R . . . .
C23 C 0.37344(10) 0.3198(2) 0.65552(10) 0.0161(4) Uani 1 1 d . . . . .
H23 H 0.415186 0.348596 0.628255 0.019 Uiso 1 1 calc R . . . .
C24 C 0.35627(12) 0.2678(3) 0.87424(11) 0.0273(5) Uani 1 1 d . . . . .
H24A H 0.356614 0.148786 0.892710 0.041 Uiso 1 1 calc GR . . . .
H24B H 0.315257 0.333292 0.894570 0.041 Uiso 1 1 calc GR . . . .
H24C H 0.411099 0.318336 0.895047 0.041 Uiso 1 1 calc GR . . . .
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'
F F 0.0171 0.0103 '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
O1 S1 N1 105.58(7) . . ?
O1 S1 C5 108.34(7) . . ?
N1 S1 C5 106.00(7) . . ?
O2 S1 O1 120.56(7) . . ?
O2 S1 N1 107.56(7) . . ?
O2 S1 C5 107.93(8) . . ?
S1 N1 H1 110.8(13) . . ?
C8 N1 S1 119.07(11) . . ?
C8 N1 H1 116.1(13) . . ?
F1 C1 F2 106.40(14) . . ?
F1 C1 C2 112.80(15) . . ?
F1 C1 F3 106.28(15) . . ?
F2 C1 C2 112.74(15) . . ?
F2 C1 F3 106.23(15) . . ?
F3 C1 C2 111.89(15) . . ?
C3 C2 C1 119.36(16) . . ?
C7 C2 C1 119.88(15) . . ?
C7 C2 C3 120.70(16) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.69(16) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.34(16) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 S1 119.52(13) . . ?
C4 C5 C6 121.35(16) . . ?
C6 C5 S1 118.94(13) . . ?
C5 C6 H6 120.5 . . ?
C5 C6 C7 118.96(16) . . ?
C7 C6 H6 120.5 . . ?
C2 C7 C6 119.93(16) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
N1 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
N1 C8 C9 110.29(13) . . ?
H8A C8 H8B 108.1 . . ?
C9 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
C8 C9 H9A 108.2 . . ?
C8 C9 H9B 108.2 . . ?
C8 C9 C10 116.23(13) . . ?
H9A C9 H9B 107.4 . . ?
C10 C9 H9A 108.2 . . ?
C10 C9 H9B 108.2 . . ?
C9 C10 H10 107.5 . . ?
C9 C10 C11 109.38(13) . . ?
C11 C10 H10 107.5 . . ?
C18 C10 C9 111.07(13) . . ?
C18 C10 H10 107.5 . . ?
C18 C10 C11 113.63(13) . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 C10 112.32(13) . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C13 C12 C11 120.06(15) . . ?
C13 C12 C17 118.37(16) . . ?
C17 C12 C11 121.53(15) . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.51(16) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.47(16) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.53(16) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.14(16) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 H17 119.5 . . ?
C16 C17 C12 120.96(16) . . ?
C16 C17 H17 119.5 . . ?
C19 C18 C10 123.01(15) . . ?
C19 C18 C23 116.97(15) . . ?
C23 C18 C10 119.95(14) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.18(16) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 119.3 . . ?
C19 C20 C21 121.47(16) . . ?
C21 C20 H20 119.3 . . ?
C20 C21 C24 121.52(16) . . ?
C22 C21 C20 117.45(15) . . ?
C22 C21 C24 121.03(16) . . ?
C21 C22 H22 119.3 . . ?
C21 C22 C23 121.31(16) . . ?
C23 C22 H22 119.3 . . ?
C18 C23 H23 119.2 . . ?
C22 C23 C18 121.57(15) . . ?
C22 C23 H23 119.2 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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 O1 1.4351(12) . ?
S1 N1 1.6211(15) . ?
S1 O2 1.4295(12) . ?
S1 C5 1.7748(17) . ?
F1 C1 1.334(2) . ?
N1 H1 0.82(2) . ?
N1 C8 1.477(2) . ?
C1 F2 1.336(2) . ?
C1 C2 1.499(2) . ?
C1 F3 1.338(2) . ?
C2 C3 1.391(2) . ?
C2 C7 1.387(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(2) . ?
C5 C6 1.389(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.390(2) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.517(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.542(2) . ?
C10 H10 1.0000 . ?
C10 C11 1.544(2) . ?
C10 C18 1.520(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.517(2) . ?
C12 C13 1.392(2) . ?
C12 C17 1.396(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.394(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.395(2) . ?
C18 C23 1.395(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.388(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.391(2) . ?
C21 C22 1.385(2) . ?
C21 C24 1.512(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.386(2) . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
