#------------------------------------------------------------------------------
#$Date: 2019-11-24 00:02:06 +0200 (Sun, 24 Nov 2019) $
#$Revision: 235684 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/71/4037119.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_4037119
loop_
_publ_author_name
'Szostak, Roman'
'Shi, Shicheng'
'Meng, Guangrong'
'Lalancette, Roger'
'Szostak, Michal'
_publ_section_title
;
 Ground-State Distortion in N-Acyl-tert-butyl-carbamates (Boc) and
 N-Acyl-tosylamides (Ts): Twisted Amides of Relevance to Amide N-C
 Cross-Coupling.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8091
_journal_page_last               8094
_journal_paper_doi               10.1021/acs.joc.6b01560
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C20 H17 N O3 S'
_chemical_formula_sum            'C20 H17 N O3 S'
_chemical_formula_weight         351.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.5517(3)
_cell_length_b                   14.7684(3)
_cell_length_c                   18.5336(4)
_cell_measurement_reflns_used    9915
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.79
_cell_measurement_theta_min      4.77
_cell_volume                     3435.55(13)
_computing_cell_refinement       'APEX 2'
_computing_data_collection       'APEX 2 (Bruker, 2006)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker SMART CCD Apex-II area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            30277
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.911
_diffrn_reflns_theta_min         4.773
_exptl_absorpt_coefficient_mu    1.832
_exptl_absorpt_correction_T_max  0.888
_exptl_absorpt_correction_T_min  0.631
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008a)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       plate
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.076
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.00029(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3089
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0285
_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)+(0.0361P)²+1.5985P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0768
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2868
_reflns_number_total             3089
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo6b01560_si_003.cif
_cod_data_source_block           160224RAL_SSC_100K_0m_a
_cod_database_code               4037119
_shelx_shelxl_version_number     2014/7
_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   0.569
_shelx_estimated_absorpt_t_max   0.873
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S 0.79760(3) 0.67136(2) 0.34509(2) 0.02073(11) Uani 1 1 d . .
O1 O 0.71697(8) 0.57523(7) 0.22231(5) 0.0272(2) Uani 1 1 d . .
O2 O 0.80120(7) 0.73485(6) 0.28726(5) 0.0255(2) Uani 1 1 d . .
O3 O 0.86055(8) 0.68630(6) 0.40839(5) 0.0262(2) Uani 1 1 d . .
N1 N 0.84126(9) 0.57069(7) 0.31236(6) 0.0202(3) Uani 1 1 d . .
C1 C 0.79425(10) 0.53804(9) 0.24833(7) 0.0212(3) Uani 1 1 d . .
C2 C 0.84515(11) 0.45743(9) 0.21433(7) 0.0215(3) Uani 1 1 d . .
C3 C 0.89727(11) 0.51019(9) 0.36091(7) 0.0202(3) Uani 1 1 d . .
C4 C 0.84333(12) 0.43724(9) 0.39052(7) 0.0240(3) Uani 1 1 d . .
H4 H 0.7697 0.4285 0.3809 0.029 Uiso 1 1 calc R U
C5 C 0.89827(14) 0.37708(10) 0.43434(8) 0.0324(4) Uani 1 1 d . .
H5 H 0.8623 0.3265 0.4546 0.039 Uiso 1 1 calc R U
C6 C 1.00548(14) 0.39063(11) 0.44858(8) 0.0371(4) Uani 1 1 d . .
H6 H 1.0430 0.3492 0.4784 0.045 Uiso 1 1 calc R U
C7 C 1.05780(12) 0.46423(11) 0.41949(8) 0.0338(4) Uani 1 1 d . .
H7 H 1.1311 0.4736 0.4299 0.041 Uiso 1 1 calc R U
C8 C 1.00429(11) 0.52462(10) 0.37531(7) 0.0258(3) Uani 1 1 d . .
H8 H 1.0404 0.5752 0.3552 0.031 Uiso 1 1 calc R U
C9 C 0.77773(12) 0.39244(10) 0.18464(7) 0.0257(3) Uani 1 1 d . .
H9 H 0.7026 0.3991 0.1886 0.031 Uiso 1 1 calc R U
C10 C 0.82025(14) 0.31833(10) 0.14942(8) 0.0325(4) Uani 1 1 d . .
H10 H 0.7742 0.2736 0.1297 0.039 Uiso 1 1 calc R U
C11 C 0.92939(14) 0.30888(10) 0.14268(8) 0.0320(4) Uani 1 1 d . .
H11 H 0.9582 0.2579 0.1182 0.038 Uiso 1 1 calc R U
C12 C 0.99678(13) 0.37383(10) 0.17166(8) 0.0290(3) Uani 1 1 d . .
H12 H 1.0718 0.3674 0.1666 0.035 Uiso 1 1 calc R U
C13 C 0.95555(11) 0.44801(10) 0.20785(7) 0.0244(3) Uani 1 1 d . .
H13 H 1.0019 0.4921 0.2281 0.029 Uiso 1 1 calc R U
C14 C 0.66499(11) 0.65496(9) 0.37276(7) 0.0211(3) Uani 1 1 d . .
C15 C 0.58115(11) 0.68301(9) 0.32922(7) 0.0221(3) Uani 1 1 d . .
H15 H 0.5944 0.7083 0.2830 0.026 Uiso 1 1 calc R U
C16 C 0.47771(12) 0.67339(9) 0.35450(7) 0.0238(3) Uani 1 1 d . .
H16 H 0.4198 0.6926 0.3252 0.029 Uiso 1 1 calc R U
C17 C 0.45745(12) 0.63588(9) 0.42231(8) 0.0247(3) Uani 1 1 d . .
C18 C 0.54343(12) 0.60872(9) 0.46461(7) 0.0260(3) Uani 1 1 d . .
H18 H 0.5305 0.5832 0.5108 0.031 Uiso 1 1 calc R U
C19 C 0.64725(12) 0.61810(9) 0.44076(7) 0.0243(3) Uani 1 1 d . .
H19 H 0.7053 0.5997 0.4702 0.029 Uiso 1 1 calc R U
C20 C 0.34525(12) 0.62675(11) 0.45025(9) 0.0325(4) Uani 1 1 d . .
H20A H 0.3410 0.5746 0.4829 0.049 Uiso 1 1 calc R U
H20B H 0.2964 0.6178 0.4096 0.049 Uiso 1 1 calc R U
H20C H 0.3254 0.6819 0.4764 0.049 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
O2 S1 O3 119.83(6)
O2 S1 N1 107.32(6)
O3 S1 N1 104.47(6)
O2 S1 C14 109.88(6)
O3 S1 C14 107.73(6)
N1 S1 C14 106.81(6)
C1 N1 C3 120.94(11)
C1 N1 S1 117.74(9)
C3 N1 S1 118.35(8)
O1 C1 N1 120.90(12)
O1 C1 C2 122.38(12)
N1 C1 C2 116.72(11)
C9 C2 C13 119.97(13)
C9 C2 C1 117.21(13)
C13 C2 C1 122.72(12)
C8 C3 C4 121.12(13)
C8 C3 N1 119.63(12)
C4 C3 N1 119.22(12)
C3 C4 C5 119.16(14)
C3 C4 H4 120.4
C5 C4 H4 120.4
C6 C5 C4 120.10(15)
C6 C5 H5 120.0
C4 C5 H5 120.0
C7 C6 C5 120.10(14)
C7 C6 H6 120.0
C5 C6 H6 120.0
C6 C7 C8 120.53(15)
C6 C7 H7 119.7
C8 C7 H7 119.7
C7 C8 C3 119.00(14)
C7 C8 H8 120.5
C3 C8 H8 120.5
C10 C9 C2 119.87(14)
C10 C9 H9 120.1
C2 C9 H9 120.1
C9 C10 C11 120.36(15)
C9 C10 H10 119.8
C11 C10 H10 119.8
C10 C11 C12 119.94(14)
C10 C11 H11 120.0
C12 C11 H11 120.0
C13 C12 C11 120.46(15)
C13 C12 H12 119.8
C11 C12 H12 119.8
C12 C13 C2 119.39(14)
C12 C13 H13 120.3
C2 C13 H13 120.3
C15 C14 C19 121.46(13)
C15 C14 S1 120.42(11)
C19 C14 S1 118.02(11)
C16 C15 C14 118.81(13)
C16 C15 H15 120.6
C14 C15 H15 120.6
C15 C16 C17 120.98(13)
C15 C16 H16 119.5
C17 C16 H16 119.5
C18 C17 C16 118.67(13)
C18 C17 C20 120.33(13)
C16 C17 C20 120.99(13)
C19 C18 C17 121.41(13)
C19 C18 H18 119.3
C17 C18 H18 119.3
C18 C19 C14 118.67(13)
C18 C19 H19 120.7
C14 C19 H19 120.7
C17 C20 H20A 109.5
C17 C20 H20B 109.5
H20A C20 H20B 109.5
C17 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.4246(10)
S1 O3 1.4312(10)
S1 N1 1.6964(11)
S1 C14 1.7578(14)
O1 C1 1.2141(16)
N1 C1 1.4100(17)
N1 C3 1.4497(16)
C1 C2 1.4907(19)
C2 C9 1.393(2)
C2 C13 1.3973(19)
C3 C8 1.3854(19)
C3 C4 1.3855(19)
C4 C5 1.387(2)
C4 H4 0.9500
C5 C6 1.385(2)
C5 H5 0.9500
C6 C7 1.379(3)
C6 H6 0.9500
C7 C8 1.384(2)
C7 H7 0.9500
C8 H8 0.9500
C9 C10 1.381(2)
C9 H9 0.9500
C10 C11 1.382(2)
C10 H10 0.9500
C11 C12 1.387(2)
C11 H11 0.9500
C12 C13 1.385(2)
C12 H12 0.9500
C13 H13 0.9500
C14 C15 1.389(2)
C14 C19 1.3905(19)
C15 C16 1.387(2)
C15 H15 0.9500
C16 C17 1.397(2)
C16 H16 0.9500
C17 C18 1.392(2)
C17 C20 1.506(2)
C18 C19 1.382(2)
C18 H18 0.9500
C19 H19 0.9500
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
