#------------------------------------------------------------------------------
#$Date: 2020-10-04 05:58:29 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257031 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/78/4517857.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_4517857
loop_
_publ_author_name
'Hu, Xinwei'
'Shao, Youxiang'
'Xie, Haisheng'
'Chen, Xin'
'Chen, Fengjuan'
'Ke, Zhuofeng'
'Jiang, Huanfeng'
'Zeng, Wei'
_publ_section_title
;
 Direct Carbon--Carbon σ Bond Amination of Unstrained Arylalkylketones
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              8402
_journal_page_last               8408
_journal_paper_doi               10.1021/acscatal.0c02683
_journal_year                    2020
_chemical_formula_moiety         'C26 H20 F N3 O2 S'
_chemical_formula_sum            'C26 H20 F N3 O2 S'
_chemical_formula_weight         457.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-06-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.357(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.9143(10)
_cell_length_b                   10.6749(6)
_cell_length_c                   20.1936(9)
_cell_measurement_reflns_used    3852
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      27.4220
_cell_measurement_theta_min      2.9230
_cell_volume                     4289.2(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -17.00  29.00   1.00    2.50    --  -11.59 -99.00 120.00   46
  2  ω     18.00  56.00   1.00    2.50    --   11.74-108.00  11.00   38
  3  ω    -60.00  76.00   1.00    2.50    --   11.74   0.00-150.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0303070500
_diffrn_orient_matrix_UB_12      0.0328346500
_diffrn_orient_matrix_UB_13      -0.0075803000
_diffrn_orient_matrix_UB_21      0.0185684000
_diffrn_orient_matrix_UB_22      0.0557454000
_diffrn_orient_matrix_UB_23      -0.0047469000
_diffrn_orient_matrix_UB_31      0.0026596500
_diffrn_orient_matrix_UB_32      -0.0151148500
_diffrn_orient_matrix_UB_33      -0.0340051000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10395
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.047
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       block
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.040
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         3776
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0489
_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)+(0.0514P)²+7.8496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1254
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3081
_reflns_number_total             3776
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c02683_si_003.cif
_cod_data_source_block           hxw-2
_cod_depositor_comments
'Adding full bibliography for 4517857--4517858.cif.'
_cod_database_code               4517857
_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.
;
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C8(H8), C5(H5), C19(H19), C10(H10), C15(H15), C21(H21), C12(H12),
 C6(H6), C7(H7), C16(H16), C17(H17), C25(H25), C24(H24), C11(H11), C18(H18)
2.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.298
_oxdiff_exptl_absorpt_empirical_full_min 0.484
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.39453(3) 0.16661(6) 0.58038(3) 0.02133(18) Uani 1 1 d . . . . .
F1 F 0.20799(8) 0.44662(18) 0.65523(8) 0.0447(5) Uani 1 1 d . . . . .
O2 O 0.35891(9) 0.05531(17) 0.59768(9) 0.0290(4) Uani 1 1 d . . . . .
O1 O 0.43841(9) 0.16578(19) 0.52596(8) 0.0292(5) Uani 1 1 d . . . . .
N1 N 0.55582(10) 0.20623(19) 0.66950(9) 0.0192(5) Uani 1 1 d . . . . .
N2 N 0.58253(10) 0.0437(2) 0.74282(9) 0.0194(5) Uani 1 1 d . . . . .
N3 N 0.43606(10) 0.2078(2) 0.64824(10) 0.0187(5) Uani 1 1 d . . . . .
C4 C 0.49759(11) 0.2723(2) 0.65041(11) 0.0168(5) Uani 1 1 d . . . . .
C1 C 0.51212(12) 0.3958(2) 0.64136(11) 0.0175(5) Uani 1 1 d . . . . .
C2 C 0.58342(12) 0.4090(2) 0.65534(10) 0.0181(5) Uani 1 1 d . . . . .
C14 C 0.46466(12) 0.4994(2) 0.62667(11) 0.0197(5) Uani 1 1 d . . . . .
C9 C 0.56145(11) 0.0752(2) 0.68130(12) 0.0189(5) Uani 1 1 d . . . . .
C13 C 0.58904(12) -0.0780(2) 0.75668(12) 0.0225(6) Uani 1 1 d . . . . .
H13 H 0.604150 -0.101416 0.799087 0.027 Uiso 1 1 calc R . . . .
C3 C 0.60855(12) 0.2910(2) 0.67432(11) 0.0192(5) Uani 1 1 d . . . . .
C20 C 0.33525(12) 0.2870(2) 0.56631(11) 0.0199(5) Uani 1 1 d . . . . .
C8 C 0.62763(13) 0.5113(3) 0.65636(11) 0.0222(6) Uani 1 1 d . . . . .
H8 H 0.612425 0.590388 0.643640 0.027 Uiso 1 1 calc R . . . .
C23 C 0.24331(12) 0.4836(2) 0.54805(11) 0.0220(6) Uani 1 1 d . . . . .
C5 C 0.67585(12) 0.2718(3) 0.69449(12) 0.0233(6) Uani 1 1 d . . . . .
H5 H 0.691615 0.192841 0.706903 0.028 Uiso 1 1 calc R . . . .
C19 C 0.47447(13) 0.5822(2) 0.57456(11) 0.0237(6) Uani 1 1 d . . . . .
H19 H 0.510925 0.571074 0.547830 0.028 Uiso 1 1 calc R . . . .
C10 C 0.54623(12) -0.0112(2) 0.63197(12) 0.0228(6) Uani 1 1 d . . . . .
H10 H 0.531919 0.014383 0.589687 0.027 Uiso 1 1 calc R . . . .
C15 C 0.40940(13) 0.5187(2) 0.66606(12) 0.0223(6) Uani 1 1 d . . . . .
H15 H 0.401634 0.464081 0.700804 0.027 Uiso 1 1 calc R . . . .
C22 C 0.24733(13) 0.4119(3) 0.60495(12) 0.0250(6) Uani 1 1 d . . . . .
C21 C 0.29097(12) 0.3145(3) 0.61584(12) 0.0232(6) Uani 1 1 d . . . . .
H21 H 0.291073 0.268317 0.654900 0.028 Uiso 1 1 calc R . . . .
C12 C 0.57429(13) -0.1705(3) 0.71075(13) 0.0266(6) Uani 1 1 d . . . . .
H12 H 0.578682 -0.254548 0.722258 0.032 Uiso 1 1 calc R . . . .
C6 C 0.71767(13) 0.3741(3) 0.69520(12) 0.0264(6) Uani 1 1 d . . . . .
H6 H 0.762656 0.364258 0.708392 0.032 Uiso 1 1 calc R . . . .
C7 C 0.69389(13) 0.4931(3) 0.67643(12) 0.0269(6) Uani 1 1 d . . . . .
H7 H 0.723297 0.560806 0.677546 0.032 Uiso 1 1 calc R . . . .
C16 C 0.36619(13) 0.6183(3) 0.65377(12) 0.0262(6) Uani 1 1 d . . . . .
H16 H 0.329851 0.630402 0.680541 0.031 Uiso 1 1 calc R . . . .
C17 C 0.37659(14) 0.7004(3) 0.60186(13) 0.0293(6) Uani 1 1 d . . . . .
H17 H 0.347599 0.767512 0.593973 0.035 Uiso 1 1 calc R . . . .
C25 C 0.33357(13) 0.3543(3) 0.50827(12) 0.0279(6) Uani 1 1 d . . . . .
H25 H 0.363020 0.335093 0.475168 0.033 Uiso 1 1 calc R . . . .
C24 C 0.28767(13) 0.4509(3) 0.49944(12) 0.0298(7) Uani 1 1 d . . . . .
H24 H 0.286439 0.495272 0.459793 0.036 Uiso 1 1 calc R . . . .
C11 C 0.55292(13) -0.1365(3) 0.64741(13) 0.0277(6) Uani 1 1 d . . . . .
H11 H 0.543139 -0.197391 0.615509 0.033 Uiso 1 1 calc R . . . .
C26 C 0.19634(14) 0.5924(3) 0.54007(13) 0.0311(7) Uani 1 1 d . . . . .
H26A H 0.150939 0.564184 0.544200 0.047 Uiso 1 1 calc GR . . . .
H26B H 0.200973 0.629385 0.497155 0.047 Uiso 1 1 calc GR . . . .
H26C H 0.206971 0.653619 0.573738 0.047 Uiso 1 1 calc GR . . . .
C18 C 0.43035(14) 0.6813(3) 0.56207(13) 0.0293(6) Uani 1 1 d . . . . .
H18 H 0.437141 0.735022 0.526706 0.035 Uiso 1 1 calc R . . . .
H3 H 0.4267(15) 0.156(3) 0.6813(15) 0.044(9) Uiso 1 1 d . . . . .
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
O2 S1 N3 104.90(11) . . ?
O2 S1 C20 108.00(11) . . ?
O1 S1 O2 120.35(12) . . ?
O1 S1 N3 110.01(11) . . ?
O1 S1 C20 107.87(11) . . ?
N3 S1 C20 104.62(11) . . ?
C4 N1 C9 126.9(2) . . ?
C3 N1 C4 107.9(2) . . ?
C3 N1 C9 125.2(2) . . ?
C13 N2 C9 117.6(2) . . ?
S1 N3 H3 110(2) . . ?
C4 N3 S1 124.72(16) . . ?
C4 N3 H3 119(2) . . ?
N1 C4 N3 118.3(2) . . ?
C1 C4 N1 110.3(2) . . ?
C1 C4 N3 131.2(2) . . ?
C4 C1 C2 106.3(2) . . ?
C4 C1 C14 127.8(2) . . ?
C2 C1 C14 125.6(2) . . ?
C3 C2 C1 107.6(2) . . ?
C8 C2 C1 133.7(2) . . ?
C8 C2 C3 118.6(2) . . ?
C19 C14 C1 121.2(2) . . ?
C19 C14 C15 118.3(2) . . ?
C15 C14 C1 120.5(2) . . ?
N2 C9 N1 114.9(2) . . ?
N2 C9 C10 123.6(2) . . ?
C10 C9 N1 121.5(2) . . ?
N2 C13 H13 118.6 . . ?
N2 C13 C12 122.7(2) . . ?
C12 C13 H13 118.6 . . ?
N1 C3 C2 107.8(2) . . ?
N1 C3 C5 129.6(2) . . ?
C5 C3 C2 122.5(2) . . ?
C21 C20 S1 118.58(18) . . ?
C25 C20 S1 120.80(19) . . ?
C25 C20 C21 120.6(2) . . ?
C2 C8 H8 120.4 . . ?
C7 C8 C2 119.2(2) . . ?
C7 C8 H8 120.4 . . ?
C22 C23 C24 115.5(2) . . ?
C22 C23 C26 122.3(2) . . ?
C24 C23 C26 122.1(2) . . ?
C3 C5 H5 121.3 . . ?
C6 C5 C3 117.3(3) . . ?
C6 C5 H5 121.3 . . ?
C14 C19 H19 119.6 . . ?
C18 C19 C14 120.8(2) . . ?
C18 C19 H19 119.6 . . ?
C9 C10 H10 121.0 . . ?
C11 C10 C9 117.9(2) . . ?
C11 C10 H10 121.0 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.6(2) . . ?
C16 C15 H15 119.7 . . ?
F1 C22 C23 117.1(2) . . ?
F1 C22 C21 118.0(2) . . ?
C21 C22 C23 124.8(2) . . ?
C20 C21 H21 121.2 . . ?
C22 C21 C20 117.5(2) . . ?
C22 C21 H21 121.2 . . ?
C13 C12 H12 120.5 . . ?
C13 C12 C11 119.0(3) . . ?
C11 C12 H12 120.5 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.3(2) . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 121.0(2) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.6(2) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.3 . . ?
C18 C17 C16 119.4(3) . . ?
C18 C17 H17 120.3 . . ?
C20 C25 H25 120.3 . . ?
C20 C25 C24 119.5(2) . . ?
C24 C25 H25 120.3 . . ?
C23 C24 H24 119.0 . . ?
C25 C24 C23 122.1(2) . . ?
C25 C24 H24 119.0 . . ?
C10 C11 C12 119.2(2) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C19 C18 H18 119.8 . . ?
C17 C18 C19 120.4(2) . . ?
C17 C18 H18 119.8 . . ?
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 1.4344(19) . ?
S1 O1 1.4320(18) . ?
S1 N3 1.631(2) . ?
S1 C20 1.760(3) . ?
F1 C22 1.359(3) . ?
N1 C4 1.398(3) . ?
N1 C9 1.423(3) . ?
N1 C3 1.387(3) . ?
N2 C9 1.338(3) . ?
N2 C13 1.335(3) . ?
N3 C4 1.405(3) . ?
N3 H3 0.89(3) . ?
C4 C1 1.364(3) . ?
C1 C2 1.443(3) . ?
C1 C14 1.477(3) . ?
C2 C3 1.403(4) . ?
C2 C8 1.402(3) . ?
C14 C19 1.394(3) . ?
C14 C15 1.399(3) . ?
C9 C10 1.382(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.378(4) . ?
C3 C5 1.400(3) . ?
C20 C21 1.392(3) . ?
C20 C25 1.374(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.378(4) . ?
C23 C22 1.380(4) . ?
C23 C24 1.392(3) . ?
C23 C26 1.496(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.373(4) . ?
C19 H19 0.9300 . ?
C19 C18 1.392(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.384(4) . ?
C22 C21 1.367(4) . ?
C21 H21 0.9300 . ?
C12 H12 0.9300 . ?
C12 C11 1.380(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.403(4) . ?
C7 H7 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.388(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(4) . ?
C25 H25 0.9300 . ?
C25 C24 1.384(4) . ?
C24 H24 0.9300 . ?
C11 H11 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C18 H18 0.9300 . ?
