#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/18/1501874.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_1501874
loop_
_publ_author_name
'Tsui, Gavin Chit'
'Glenadel, Quentin'
'Lau, Chan'
'Lautens, Mark'
_publ_section_title
;
 Rhodium(I)-catalyzed addition of arylboronic acids to
 (benzyl-/arylsulfonyl)acetonitriles: efficient synthesis of
 (Z)-β-sulfonylvinylamines and β-keto sulfones.
;
_journal_issue                   2
_journal_name_full               'Organic letters'
_journal_page_first              208
_journal_page_last               211
_journal_paper_doi               10.1021/ol102598p
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C21 H19 N O3 S'
_chemical_formula_sum            'C21 H19 N O3 S'
_chemical_formula_weight         365.43
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.385(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6221(3)
_cell_length_b                   8.9558(4)
_cell_length_c                   21.2803(10)
_cell_measurement_reflns_used    7652
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     1803.76(13)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0903
_diffrn_reflns_av_sigmaI/netI    0.0899
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16779
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.709
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4115
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1440
_refine_ls_R_factor_gt           0.0629
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0949P)²+0.2929P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1471
_refine_ls_wR_factor_ref         0.1909
_reflns_number_gt                2168
_reflns_number_total             4115
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ol102598p_si_003.cif
_cod_data_source_block           k10239
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1501874
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.12766(8) 0.36880(9) 0.41000(4) 0.0365(3) Uani 1 1 d .
O1 O 0.1711(2) 0.2220(2) 0.39421(11) 0.0440(6) Uani 1 1 d .
O2 O 0.0770(2) 0.3859(2) 0.46972(10) 0.0412(6) Uani 1 1 d .
O3 O 0.7108(2) 1.0450(2) 0.42366(11) 0.0472(6) Uani 1 1 d .
N1 N 0.2017(3) 0.6695(4) 0.48552(16) 0.0529(8) Uani 1 1 d .
H1N H 0.240(4) 0.744(4) 0.5121(18) 0.060(11) Uiso 1 1 d .
H2N H 0.128(4) 0.609(4) 0.4977(18) 0.060(10) Uiso 1 1 d .
C1 C 0.2817(3) 0.6237(3) 0.44250(15) 0.0352(7) Uani 1 1 d .
C2 C 0.2631(3) 0.4962(3) 0.40681(15) 0.0354(7) Uani 1 1 d .
C3 C 0.3429(3) 0.4632(3) 0.35367(15) 0.0365(7) Uani 1 1 d .
C4 C 0.2984(4) 0.5173(4) 0.29280(17) 0.0478(9) Uani 1 1 d .
H4A H 0.2201 0.5834 0.2843 0.057 Uiso 1 1 calc R
C5 C 0.3680(4) 0.4754(4) 0.24369(18) 0.0576(10) Uani 1 1 d .
H5A H 0.3361 0.5126 0.2018 0.069 Uiso 1 1 calc R
C6 C 0.4824(4) 0.3807(4) 0.2550(2) 0.0574(11) Uani 1 1 d .
H6A H 0.5282 0.3513 0.2210 0.069 Uiso 1 1 calc R
C7 C 0.5298(4) 0.3290(4) 0.3160(2) 0.0556(10) Uani 1 1 d .
H7A H 0.6102 0.2657 0.3244 0.067 Uiso 1 1 calc R
C8 C 0.4605(3) 0.3691(3) 0.36515(17) 0.0422(8) Uani 1 1 d .
H8A H 0.4933 0.3323 0.4071 0.051 Uiso 1 1 calc R
C9 C -0.0099(3) 0.4266(4) 0.34822(15) 0.0397(8) Uani 1 1 d .
C10 C -0.0203(4) 0.3658(4) 0.28815(17) 0.0519(9) Uani 1 1 d .
H10A H 0.0394 0.2854 0.2809 0.062 Uiso 1 1 calc R
C11 C -0.1190(4) 0.4232(5) 0.23814(19) 0.0627(11) Uani 1 1 d .
H11A H -0.1275 0.3813 0.1966 0.075 Uiso 1 1 calc R
C12 C -0.2045(4) 0.5407(5) 0.2487(2) 0.0605(11) Uani 1 1 d .
H12A H -0.2697 0.5819 0.2141 0.073 Uiso 1 1 calc R
C13 C -0.1954(4) 0.5986(4) 0.3094(2) 0.0593(10) Uani 1 1 d .
H13A H -0.2567 0.6772 0.3169 0.071 Uiso 1 1 calc R
C14 C -0.0978(3) 0.5427(4) 0.35924(18) 0.0491(9) Uani 1 1 d .
H14A H -0.0908 0.5835 0.4009 0.059 Uiso 1 1 calc R
C15 C 0.3970(3) 0.7310(3) 0.43620(14) 0.0353(7) Uani 1 1 d .
C16 C 0.3660(3) 0.8812(4) 0.42350(15) 0.0382(8) Uani 1 1 d .
H16A H 0.2707 0.9141 0.4181 0.046 Uiso 1 1 calc R
C17 C 0.4714(3) 0.9831(3) 0.41862(15) 0.0401(8) Uani 1 1 d .
H17A H 0.4485 1.0846 0.4089 0.048 Uiso 1 1 calc R
C18 C 0.6115(3) 0.9358(4) 0.42804(14) 0.0380(8) Uani 1 1 d .
C19 C 0.6442(3) 0.7872(4) 0.44110(15) 0.0403(8) Uani 1 1 d .
H19A H 0.7396 0.7546 0.4473 0.048 Uiso 1 1 calc R
C20 C 0.5370(3) 0.6862(4) 0.44515(15) 0.0396(8) Uani 1 1 d .
H20A H 0.5600 0.5844 0.4542 0.048 Uiso 1 1 calc R
C21 C 0.8532(3) 0.9965(5) 0.4278(2) 0.0660(11) Uani 1 1 d .
H21A H 0.9128 1.0820 0.4215 0.099 Uiso 1 1 calc R
H21B H 0.8580 0.9213 0.3948 0.099 Uiso 1 1 calc R
H21C H 0.8869 0.9529 0.4701 0.099 Uiso 1 1 calc R
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
O1 S1 O2 117.36(13)
O1 S1 C2 109.78(13)
O2 S1 C2 109.70(14)
O1 S1 C9 107.71(15)
O2 S1 C9 107.24(13)
C2 S1 C9 104.17(14)
C18 O3 C21 116.7(3)
N1 C1 C2 126.4(3)
N1 C1 C15 112.7(3)
C2 C1 C15 120.9(3)
C1 C2 C3 123.3(3)
C1 C2 S1 123.3(2)
C3 C2 S1 112.8(2)
C4 C3 C8 118.8(3)
C4 C3 C2 121.6(3)
C8 C3 C2 119.6(3)
C3 C4 C5 120.2(3)
C6 C5 C4 120.8(4)
C7 C6 C5 119.4(3)
C6 C7 C8 120.1(4)
C7 C8 C3 120.6(3)
C10 C9 C14 120.6(3)
C10 C9 S1 119.6(3)
C14 C9 S1 119.5(3)
C9 C10 C11 119.3(4)
C12 C11 C10 120.2(4)
C11 C12 C13 119.9(4)
C14 C13 C12 120.3(4)
C13 C14 C9 119.6(3)
C20 C15 C16 118.4(3)
C20 C15 C1 121.5(3)
C16 C15 C1 120.1(3)
C17 C16 C15 121.1(3)
C16 C17 C18 119.5(3)
O3 C18 C19 124.0(3)
O3 C18 C17 116.0(3)
C19 C18 C17 120.0(3)
C18 C19 C20 119.7(3)
C15 C20 C19 121.2(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.437(2)
S1 O2 1.449(2)
S1 C2 1.743(3)
S1 C9 1.767(3)
O3 C18 1.382(4)
O3 C21 1.425(4)
N1 C1 1.361(4)
C1 C2 1.365(4)
C1 C15 1.492(4)
C2 C3 1.506(4)
C3 C4 1.377(5)
C3 C8 1.397(4)
C4 C5 1.390(5)
C5 C6 1.376(5)
C6 C7 1.376(5)
C7 C8 1.385(5)
C9 C10 1.377(5)
C9 C14 1.387(4)
C10 C11 1.391(5)
C11 C12 1.379(5)
C12 C13 1.381(5)
C13 C14 1.377(5)
C15 C20 1.385(4)
C15 C16 1.394(4)
C16 C17 1.382(4)
C17 C18 1.393(4)
C18 C19 1.384(4)
C19 C20 1.386(4)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O3 0.91(4) 2.33(4) 3.225(4) 168(3) 3_676
N1 H2N O2 0.96(4) 2.12(4) 2.803(4) 127(3) .
N1 H2N O2 0.96(4) 2.21(4) 3.044(3) 145(3) 3_566
