#------------------------------------------------------------------------------
#$Date: 2015-10-26 15:19:24 +0200 (Mon, 26 Oct 2015) $
#$Revision: 169748 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/79/7117992.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_7117992
loop_
_publ_author_name
'Zhen-Hua Wang'
'Zhi-Jun Wu'
'Xue-Qun Huang'
'Deng-Feng Yue'
'Yong You'
'Xiao-Ying Xu'
'Xiao-Mei Zhang'
'Wei-Cheng Yuan'
_publ_section_title
;
 Diastereo- and enantioselective direct vinylogous Michael addition of
 gamma-substituted butenolides to 2-enoylpyridines catalyzed by chiral
 bifunctional amine-squaramides
;
_journal_name_full               Chem.Commun.
_journal_page_first              15835
_journal_paper_doi               10.1039/C5cc06383C
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H17 N O3 S'
_chemical_formula_weight         375.30
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-03-31 deposited with the CCDC.
2015-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.466(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.9821(9)
_cell_length_b                   6.4380(3)
_cell_length_c                   15.2420(5)
_cell_measurement_reflns_used    7000
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      69.1640
_cell_measurement_theta_min      4.5270
_cell_volume                     1916.11(14)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_laue_measured_fraction_full 0.995
_diffrn_reflns_laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12444
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.700
_diffrn_reflns_theta_min         4.529
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.679
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.310
_refine_diff_density_max         0.991
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.066(58)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3429
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0788
_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)+(0.1595P)²+1.3887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2317
_refine_ls_wR_factor_ref         0.2342
_reflns_Friedel_coverage         0.743
_reflns_friedel_fraction_full    0.909
_reflns_friedel_fraction_max     0.890
_reflns_number_gt                3320
_reflns_number_total             3429
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc06383c2.cif
_cod_data_source_block           shelxl
_cod_database_code               7117992
_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   0.560
_shelx_estimated_absorpt_t_max   0.624
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.35338(10) 0.4927(4) 0.12041(13) 0.0915(7) Uani 1 1 d . U . . .
O3 O 0.2183(2) 0.6624(8) 0.2051(4) 0.0761(13) Uani 1 1 d . . . . .
O1 O 0.36744(17) 0.0278(6) 0.3395(3) 0.0543(8) Uani 1 1 d . . . . .
O2 O 0.4344(3) -0.2307(8) 0.3257(4) 0.0868(14) Uani 1 1 d . . . . .
N1 N 0.1021(3) 0.2640(12) 0.1936(6) 0.098(2) Uani 1 1 d . . . . .
C4 C 0.3733(2) 0.2488(7) 0.3564(3) 0.0462(10) Uani 1 1 d . . . . .
C10 C 0.3344(3) 0.1498(12) 0.4895(4) 0.0672(15) Uani 1 1 d . . . . .
H10 H 0.3229 0.0183 0.4632 0.081 Uiso 1 1 calc R U . . .
C12 C 0.2457(2) 0.3202(9) 0.2646(4) 0.0544(12) Uani 1 1 d . . . . .
H12A H 0.2302 0.1915 0.2303 0.065 Uiso 1 1 calc R U . . .
H12B H 0.2449 0.3022 0.3274 0.065 Uiso 1 1 calc R U . . .
C7 C 0.3716(4) 0.5364(14) 0.5720(5) 0.085(2) Uani 1 1 d . . . . .
H7 H 0.3858 0.6639 0.6014 0.101 Uiso 1 1 calc R U . . .
C9 C 0.3232(4) 0.2022(16) 0.5716(5) 0.086(2) Uani 1 1 d . . . . .
H9 H 0.3032 0.1057 0.5989 0.103 Uiso 1 1 calc R U . . .
C1 C 0.4279(3) -0.0476(9) 0.3374(4) 0.0591(12) Uani 1 1 d . . . . .
C3 C 0.4453(2) 0.2953(8) 0.3619(3) 0.0496(11) Uani 1 1 d . . . . .
H3 H 0.4651 0.4266 0.3708 0.060 Uiso 1 1 calc R U . . .
C19 C 0.3265(2) 0.3178(9) 0.1789(3) 0.0524(11) Uani 1 1 d . U . . .
C20 C 0.30717(19) 0.1266(9) 0.1210(3) 0.0494(11) Uani 1 1 d . U . . .
H20 H 0.2899 0.0054 0.1371 0.059 Uiso 1 1 calc R U . . .
C14 C 0.1222(3) 0.4535(12) 0.1846(4) 0.0637(15) Uani 1 1 d . . . . .
C2 C 0.4755(2) 0.1250(9) 0.3524(4) 0.0566(12) Uani 1 1 d . . . . .
H2 H 0.5204 0.1150 0.3548 0.068 Uiso 1 1 calc R U . . .
C6 C 0.3809(3) 0.4920(11) 0.4893(4) 0.0672(14) Uani 1 1 d . . . . .
H6 H 0.3990 0.5923 0.4612 0.081 Uiso 1 1 calc R U . . .
C11 C 0.3192(2) 0.3636(9) 0.2721(3) 0.0481(10) Uani 1 1 d . . . . .
H11 H 0.3271 0.5129 0.2838 0.058 Uiso 1 1 calc R U . . .
C13 C 0.1974(2) 0.4918(10) 0.2155(3) 0.0547(13) Uani 1 1 d . . . . .
C5 C 0.3632(2) 0.2966(9) 0.4473(3) 0.0517(11) Uani 1 1 d . . . . .
C8 C 0.3411(4) 0.3916(16) 0.6121(5) 0.088(2) Uani 1 1 d . . . . .
H8 H 0.3330 0.4247 0.6665 0.106 Uiso 1 1 calc R U . . .
C21 C 0.3197(4) 0.161(2) 0.0366(5) 0.099(2) Uani 1 1 d . U . . .
H21 H 0.3117 0.0595 -0.0095 0.119 Uiso 1 1 calc R U . . .
C22 C 0.3424(4) 0.340(2) 0.0282(5) 0.101(2) Uani 1 1 d . U . . .
H22 H 0.3520 0.3809 -0.0242 0.121 Uiso 1 1 calc R U . . .
C17 C -0.0130(3) 0.3908(18) 0.1335(8) 0.111(3) Uani 1 1 d . . . . .
H17 H -0.0595 0.3620 0.1148 0.133 Uiso 1 1 calc R U . . .
C15 C 0.0776(3) 0.6185(14) 0.1531(5) 0.0793(19) Uani 1 1 d . . . . .
H15 H 0.0941 0.7514 0.1502 0.095 Uiso 1 1 calc R U . . .
C18 C 0.0359(4) 0.2336(18) 0.1700(10) 0.123(4) Uani 1 1 d . . . . .
H18 H 0.0208 0.1017 0.1780 0.148 Uiso 1 1 calc R U . . .
C16 C 0.0088(4) 0.5831(17) 0.1261(7) 0.098(3) Uani 1 1 d . . . . .
H16 H -0.0224 0.6910 0.1029 0.117 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 0.0180 0.0090 '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 0.0310 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0490 0.0320 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3330 0.5570 '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
C19 S1 C22 94.8(4) . .
C1 O1 C4 109.5(4) . .
C14 N1 C18 117.2(7) . .
O1 C4 C5 109.4(4) . .
O1 C4 C3 102.9(4) . .
C5 C4 C3 112.5(4) . .
O1 C4 C11 109.5(4) . .
C5 C4 C11 110.9(4) . .
C3 C4 C11 111.4(4) . .
C9 C10 C5 119.4(7) . .
C9 C10 H10 120.3 . .
C5 C10 H10 120.3 . .
C13 C12 C11 112.4(5) . .
C13 C12 H12A 109.1 . .
C11 C12 H12A 109.1 . .
C13 C12 H12B 109.1 . .
C11 C12 H12B 109.1 . .
H12A C12 H12B 107.9 . .
C6 C7 C8 120.3(8) . .
C6 C7 H7 119.8 . .
C8 C7 H7 119.8 . .
C8 C9 C10 121.1(7) . .
C8 C9 H9 119.5 . .
C10 C9 H9 119.5 . .
O2 C1 O1 120.4(6) . .
O2 C1 C2 131.3(6) . .
O1 C1 C2 108.4(5) . .
C2 C3 C4 110.2(4) . .
C2 C3 H3 124.9 . .
C4 C3 H3 124.9 . .
C20 C19 C11 128.4(5) . .
C20 C19 S1 108.5(4) . .
C11 C19 S1 123.0(4) . .
C21 C20 C19 107.9(7) . .
C21 C20 H20 126.1 . .
C19 C20 H20 126.1 . .
N1 C14 C15 123.2(6) . .
N1 C14 C13 117.6(5) . .
C15 C14 C13 119.1(7) . .
C3 C2 C1 109.0(4) . .
C3 C2 H2 125.5 . .
C1 C2 H2 125.5 . .
C7 C6 C5 120.3(7) . .
C7 C6 H6 119.8 . .
C5 C6 H6 119.8 . .
C19 C11 C12 109.8(4) . .
C19 C11 C4 112.8(4) . .
C12 C11 C4 112.8(4) . .
C19 C11 H11 107.0 . .
C12 C11 H11 107.0 . .
C4 C11 H11 107.0 . .
O3 C13 C14 119.9(5) . .
O3 C13 C12 121.4(4) . .
C14 C13 C12 118.6(5) . .
C10 C5 C6 118.9(5) . .
C10 C5 C4 121.0(5) . .
C6 C5 C4 120.1(5) . .
C9 C8 C7 119.8(6) . .
C9 C8 H8 120.1 . .
C7 C8 H8 120.1 . .
C22 C21 C20 115.7(8) . .
C22 C21 H21 122.1 . .
C20 C21 H21 122.1 . .
C21 C22 S1 113.1(6) . .
C21 C22 H22 123.4 . .
S1 C22 H22 123.4 . .
C16 C17 C18 118.5(7) . .
C16 C17 H17 120.7 . .
C18 C17 H17 120.7 . .
C16 C15 C14 118.9(9) . .
C16 C15 H15 120.5 . .
C14 C15 H15 120.5 . .
N1 C18 C17 123.1(10) . .
N1 C18 H18 118.4 . .
C17 C18 H18 118.4 . .
C17 C16 C15 118.9(8) . .
C17 C16 H16 120.5 . .
C15 C16 H16 120.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C19 1.658(6) .
S1 C22 1.661(11) .
O3 C13 1.214(8) .
O1 C1 1.369(7) .
O1 C4 1.443(6) .
O2 C1 1.208(8) .
N1 C14 1.315(10) .
N1 C18 1.316(10) .
C4 C5 1.508(6) .
C4 C3 1.511(6) .
C4 C11 1.555(6) .
C10 C9 1.395(9) .
C10 C5 1.399(8) .
C10 H10 0.9300 .
C12 C13 1.501(7) .
C12 C11 1.529(6) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C7 C6 1.374(9) .
C7 C8 1.392(13) .
C7 H7 0.9300 .
C9 C8 1.356(14) .
C9 H9 0.9300 .
C1 C2 1.456(8) .
C3 C2 1.301(8) .
C3 H3 0.9300 .
C19 C20 1.482(7) .
C19 C11 1.514(6) .
C20 C21 1.422(10) .
C20 H20 0.9300 .
C14 C15 1.380(10) .
C14 C13 1.492(7) .
C2 H2 0.9300 .
C6 C5 1.399(9) .
C6 H6 0.9300 .
C11 H11 0.9800 .
C8 H8 0.9300 .
C21 C22 1.269(15) .
C21 H21 0.9300 .
C22 H22 0.9300 .
C17 C16 1.339(14) .
C17 C18 1.403(14) .
C17 H17 0.9300 .
C15 C16 1.368(10) .
C15 H15 0.9300 .
C18 H18 0.9300 .
C16 H16 0.9300 .
