#------------------------------------------------------------------------------
#$Date: 2019-11-25 18:05:05 +0100 (lun 25 de nov de 2019) $
#$Revision: 241597 $
#$URL: svn://www.crystallography.net/cod/cif/4/13/13/4131376.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_4131376
loop_
_publ_author_name
'Li, Beryl X.'
'Le, Diane N.'
'Mack, Kyle A.'
'McClory, Andrew'
'Lim, Ngiap-Kie'
'Cravillion, Theresa'
'Savage, Scott'
'Han, Chong'
'Collum, David B.'
'Zhang, Haiming'
'Gosselin, Francis'
_publ_section_title
;
 Highly Stereoselective Synthesis of Tetrasubstituted Acyclic All-Carbon
 Olefins via Enol Tosylation and Suzuki-Miyaura Coupling.
;
_journal_issue                   31
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10777
_journal_page_last               10783
_journal_paper_doi               10.1021/jacs.7b05071
_journal_volume                  139
_journal_year                    2017
_chemical_formula_sum            'C22 H21 N O3 S'
_chemical_formula_weight         379.46
_chemical_name_common            71452-126
_chemical_name_systematic        gene893
_space_group.centring_type       primitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 107.6580(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5238(8)
_cell_length_b                   9.4922(6)
_cell_length_c                   16.7995(11)
_cell_measurement_reflns_used    8814
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.36
_cell_measurement_theta_min      2.49
_cell_volume                     1903.0(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-2016
_computing_structure_solution    'SHELXT 2014'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0535
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_refln_scan_rate          10
_diffrn_refln_scan_width         2.0
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19286
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.369
_diffrn_reflns_theta_min         1.706
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.070
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3489
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0364P)²+1.4188P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0971
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2883
_reflns_number_total             3489
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja-2017-050714-File022.cif
_cod_data_source_block           71452-126
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4131376
_shelx_shelxl_version_number     2016/6
_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_min   0.987
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
C1 C 0.28042(15) 0.4741(2) 0.47103(11) 0.0153(4) Uani 1 1 d . .
C2 C 0.36923(16) 0.4043(2) 0.52729(11) 0.0186(4) Uani 1 1 d . .
H2 H 0.439264 0.450116 0.550303 0.022 Uiso 1 1 calc R U
C3 C 0.35403(16) 0.2669(2) 0.54925(11) 0.0208(4) Uani 1 1 d . .
H3 H 0.414529 0.218498 0.587463 0.025 Uiso 1 1 calc R U
C4 C 0.25184(16) 0.1983(2) 0.51645(11) 0.0199(4) Uani 1 1 d . .
C5 C 0.16411(16) 0.2716(2) 0.46062(12) 0.0227(5) Uani 1 1 d . .
H5 H 0.093777 0.226368 0.437849 0.027 Uiso 1 1 calc R U
C6 C 0.17749(16) 0.4087(2) 0.43780(12) 0.0209(4) Uani 1 1 d . .
H6 H 0.116988 0.457538 0.399850 0.025 Uiso 1 1 calc R U
C7 C 0.23549(19) 0.0496(2) 0.54086(13) 0.0281(5) Uani 1 1 d . .
H7A H 0.199275 0.050322 0.585021 0.042 Uiso 1 1 calc R U
H7B H 0.308430 0.002725 0.561341 0.042 Uiso 1 1 calc R U
H7C H 0.188099 -0.001217 0.492142 0.042 Uiso 1 1 calc R U
C8 C 0.26680(14) 0.6574(2) 0.28293(10) 0.0141(4) Uani 1 1 d . .
C9 C 0.27393(14) 0.7725(2) 0.23892(11) 0.0144(4) Uani 1 1 d . .
C10 C 0.21218(15) 0.7836(2) 0.14645(11) 0.0166(4) Uani 1 1 d . .
H10A H 0.170611 0.694926 0.127517 0.020 Uiso 1 1 calc R U
H10B H 0.267470 0.794746 0.115468 0.020 Uiso 1 1 calc R U
C11 C 0.13028(16) 0.9066(2) 0.12549(12) 0.0237(5) Uani 1 1 d . .
H11A H 0.079361 0.900755 0.159623 0.035 Uiso 1 1 calc R U
H11B H 0.086844 0.902727 0.066210 0.035 Uiso 1 1 calc R U
H11C H 0.171945 0.995489 0.137155 0.035 Uiso 1 1 calc R U
C12 C 0.19889(15) 0.5293(2) 0.25324(10) 0.0157(4) Uani 1 1 d . .
C13 C 0.25113(16) 0.3980(2) 0.26218(11) 0.0194(4) Uani 1 1 d . .
H13 H 0.329275 0.390651 0.289791 0.023 Uiso 1 1 calc R U
C14 C 0.18945(17) 0.2781(2) 0.23092(12) 0.0229(5) Uani 1 1 d . .
H14 H 0.225554 0.189051 0.236674 0.028 Uiso 1 1 calc R U
C15 C 0.07504(17) 0.2880(2) 0.19122(12) 0.0240(5) Uani 1 1 d . .
H15 H 0.033308 0.205896 0.168804 0.029 Uiso 1 1 calc R U
C16 C 0.02166(17) 0.4170(2) 0.18423(12) 0.0224(5) Uani 1 1 d . .
H16 H -0.056995 0.423214 0.158460 0.027 Uiso 1 1 calc R U
C17 C 0.08338(16) 0.5376(2) 0.21502(11) 0.0190(4) Uani 1 1 d . .
H17 H 0.046676 0.626194 0.210003 0.023 Uiso 1 1 calc R U
C18 C 0.34856(14) 0.8940(2) 0.27452(11) 0.0145(4) Uani 1 1 d . .
C19 C 0.35320(15) 0.9583(2) 0.35025(11) 0.0175(4) Uani 1 1 d . .
H19 H 0.309489 0.923022 0.383226 0.021 Uiso 1 1 calc R U
C20 C 0.42215(16) 1.0738(2) 0.37672(12) 0.0207(4) Uani 1 1 d . .
H20 H 0.427320 1.117875 0.428526 0.025 Uiso 1 1 calc R U
C21 C 0.48356(16) 1.1244(2) 0.32676(12) 0.0195(4) Uani 1 1 d . .
H21 H 0.531778 1.203446 0.343283 0.023 Uiso 1 1 calc R U
C22 C 0.47224(15) 1.0560(2) 0.25213(11) 0.0191(4) Uani 1 1 d . .
H22 H 0.513560 1.091437 0.217466 0.023 Uiso 1 1 calc R U
N1 N 0.40711(13) 0.94339(17) 0.22525(9) 0.0176(4) Uani 1 1 d . .
O1 O 0.19056(10) 0.71740(14) 0.41943(8) 0.0193(3) Uani 1 1 d . .
O2 O 0.38869(11) 0.70940(14) 0.50837(7) 0.0201(3) Uani 1 1 d . .
O3 O 0.34350(10) 0.64388(14) 0.36534(7) 0.0142(3) Uani 1 1 d . .
S1 S 0.29747(4) 0.64974(5) 0.44498(3) 0.01460(14) Uani 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'
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
C6 C1 C2 121.00(18)
C6 C1 S1 119.60(15)
C2 C1 S1 119.36(14)
C3 C2 C1 118.95(18)
C3 C2 H2 120.5
C1 C2 H2 120.5
C2 C3 C4 121.30(18)
C2 C3 H3 119.4
C4 C3 H3 119.4
C3 C4 C5 118.36(18)
C3 C4 C7 121.13(18)
C5 C4 C7 120.51(18)
C6 C5 C4 121.29(19)
C6 C5 H5 119.4
C4 C5 H5 119.4
C5 C6 C1 119.10(18)
C5 C6 H6 120.5
C1 C6 H6 120.5
C4 C7 H7A 109.5
C4 C7 H7B 109.5
H7A C7 H7B 109.5
C4 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C9 C8 O3 118.06(16)
C9 C8 C12 127.77(16)
O3 C8 C12 113.60(15)
C8 C9 C18 123.31(16)
C8 C9 C10 121.65(17)
C18 C9 C10 114.89(16)
C9 C10 C11 112.87(15)
C9 C10 H10A 109.0
C11 C10 H10A 109.0
C9 C10 H10B 109.0
C11 C10 H10B 109.0
H10A C10 H10B 107.8
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C13 C12 C17 119.11(18)
C13 C12 C8 119.67(16)
C17 C12 C8 121.21(18)
C14 C13 C12 120.24(18)
C14 C13 H13 119.9
C12 C13 H13 119.9
C13 C14 C15 120.2(2)
C13 C14 H14 119.9
C15 C14 H14 119.9
C16 C15 C14 120.14(19)
C16 C15 H15 119.9
C14 C15 H15 119.9
C15 C16 C17 119.84(18)
C15 C16 H16 120.1
C17 C16 H16 120.1
C16 C17 C12 120.46(19)
C16 C17 H17 119.8
C12 C17 H17 119.8
N1 C18 C19 121.92(17)
N1 C18 C9 114.52(15)
C19 C18 C9 123.45(16)
C20 C19 C18 119.25(17)
C20 C19 H19 120.4
C18 C19 H19 120.4
C19 C20 C21 119.18(17)
C19 C20 H20 120.4
C21 C20 H20 120.4
C22 C21 C20 117.66(18)
C22 C21 H21 121.2
C20 C21 H21 121.2
N1 C22 C21 124.51(17)
N1 C22 H22 117.7
C21 C22 H22 117.7
C22 N1 C18 117.46(16)
C8 O3 S1 119.74(10)
O2 S1 O1 120.86(8)
O2 S1 O3 103.13(7)
O1 S1 O3 107.75(7)
O2 S1 C1 108.83(8)
O1 S1 C1 109.19(8)
O3 S1 C1 106.01(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.386(3)
C1 C2 1.390(3)
C1 S1 1.753(2)
C2 C3 1.384(3)
C2 H2 0.9500
C3 C4 1.392(3)
C3 H3 0.9500
C4 C5 1.395(3)
C4 C7 1.501(3)
C5 C6 1.381(3)
C5 H5 0.9500
C6 H6 0.9500
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 C9 1.337(3)
C8 O3 1.431(2)
C8 C12 1.481(3)
C9 C18 1.491(3)
C9 C10 1.514(2)
C10 C11 1.523(3)
C10 H10A 0.9900
C10 H10B 0.9900
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 C13 1.395(3)
C12 C17 1.396(3)
C13 C14 1.386(3)
C13 H13 0.9500
C14 C15 1.388(3)
C14 H14 0.9500
C15 C16 1.383(3)
C15 H15 0.9500
C16 C17 1.390(3)
C16 H16 0.9500
C17 H17 0.9500
C18 N1 1.346(2)
C18 C19 1.396(3)
C19 C20 1.383(3)
C19 H19 0.9500
C20 C21 1.385(3)
C20 H20 0.9500
C21 C22 1.380(3)
C21 H21 0.9500
C22 N1 1.338(2)
C22 H22 0.9500
O1 S1 1.4285(13)
O2 S1 1.4219(13)
O3 S1 1.6105(12)
