#------------------------------------------------------------------------------
#$Date: 2017-12-11 00:28:22 +0100 (lun 11 de dic de 2017) $
#$Revision: 204147 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/03/4030321.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_4030321
loop_
_publ_author_name
'Fauber, Benjamin P.'
'Clagg, Kyle'
'Gibbons, Paul'
'Rene, Olivier'
_publ_section_title
;
 An Experimental and Computational Study of the Diastereoselective
 Alkylations of 3-Substituted gamma-Sultams.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              685
_journal_paper_doi               10.1021/jo502506j
_journal_volume                  80
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C10 H13 N O2 S'
_chemical_formula_weight         211.27
_chemical_name_common            Compound_1a
_chemical_name_systematic
; 
 gene191 
;
_space_group.centring_type       P
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 101.765(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.4713(2)
_cell_length_b                   6.9416(2)
_cell_length_c                   11.6404(4)
_cell_measurement_reflns_used    9608
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.24
_cell_measurement_theta_min      3.88
_cell_volume                     511.92(3)
_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-2013
_computing_structure_solution    SHELXT
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_refln_scan_rate          10
_diffrn_refln_scan_width         2.0
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11863
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.236
_diffrn_reflns_theta_min         3.879
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    2.601
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       plate
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
; 
 Flack x determined using 814 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.007(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1841
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0294
_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)+(0.0533P)²+0.1474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0780
_reflns_Friedel_coverage         0.810
_reflns_Friedel_fraction_full    0.964
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                1818
_reflns_number_total             1841
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo502506j_si_001.cif
_cod_data_source_block           Compound_1a
_cod_depositor_comments
;Adding full bibliography for 4030321.cif.

The following automatic conversions were performed:

'_space_group.centring_type' value 'primitive' was replaced with the
value 'P' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5642 2017-10-24 12:04:52Z antanas 
;
_cod_database_code               4030321
#BEGIN Tags that were not found in dictionaries:
_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   0.903
_shelx_estimated_absorpt_t_max   0.974
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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
C1 C 0.5402(4) 0.2460(4) 0.6944(2) 0.0210(5) Uani 1 1 d . .
H1 H 0.6289 0.2756 0.6356 0.025 Uiso 1 1 calc R U
C2 C 0.3424(5) 0.1362(4) 0.6341(3) 0.0273(6) Uani 1 1 d . .
H2A H 0.3807 0.0278 0.5873 0.033 Uiso 1 1 calc R U
H2B H 0.2664 0.0843 0.6931 0.033 Uiso 1 1 calc R U
C3 C 0.2058(5) 0.2817(5) 0.5551(3) 0.0352(7) Uani 1 1 d . .
H3A H 0.0545 0.2473 0.5439 0.042 Uiso 1 1 calc R U
H3B H 0.2453 0.2882 0.4774 0.042 Uiso 1 1 calc R U
C4 C 0.6138(4) 0.5764(4) 0.7796(3) 0.0274(6) Uani 1 1 d . .
H4A H 0.7005 0.5328 0.8541 0.041 Uiso 1 1 calc R U
H4B H 0.5409 0.6958 0.7924 0.041 Uiso 1 1 calc R U
H4C H 0.7042 0.6000 0.7230 0.041 Uiso 1 1 calc R U
C5 C 0.6703(4) 0.1357(4) 0.7955(2) 0.0199(5) Uani 1 1 d . .
C6 C 0.8520(4) 0.0412(4) 0.7800(2) 0.0240(6) Uani 1 1 d . .
H6 H 0.8968 0.0527 0.7075 0.029 Uiso 1 1 calc R U
C7 C 0.9684(4) -0.0695(4) 0.8692(3) 0.0268(6) Uani 1 1 d . .
H7 H 1.0908 -0.1354 0.8571 0.032 Uiso 1 1 calc R U
C8 C 0.9068(4) -0.0842(4) 0.9759(3) 0.0261(6) Uani 1 1 d . .
H8 H 0.9874 -0.1593 1.0373 0.031 Uiso 1 1 calc R U
C9 C 0.7270(4) 0.0111(5) 0.9932(2) 0.0251(5) Uani 1 1 d . .
H9 H 0.6854 0.0025 1.0667 0.030 Uiso 1 1 calc R U
C10 C 0.6075(4) 0.1195(4) 0.9027(2) 0.0224(6) Uani 1 1 d . .
H10 H 0.4829 0.1825 0.9141 0.027 Uiso 1 1 calc R U
N1 N 0.4574(3) 0.4276(3) 0.73352(19) 0.0206(5) Uani 1 1 d . .
O1 O 0.3262(4) 0.6466(3) 0.55624(18) 0.0364(5) Uani 1 1 d . .
O2 O 0.0889(4) 0.5641(4) 0.6856(2) 0.0510(8) Uani 1 1 d . .
S1 S 0.25792(9) 0.50601(9) 0.63137(5) 0.0236(2) 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 0.0181 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
N1 C1 C5 111.9(2)
N1 C1 C2 104.1(2)
C5 C1 C2 112.7(2)
N1 C1 H1 109.3
C5 C1 H1 109.3
C2 C1 H1 109.3
C3 C2 C1 105.9(2)
C3 C2 H2A 110.5
C1 C2 H2A 110.5
C3 C2 H2B 110.5
C1 C2 H2B 110.5
H2A C2 H2B 108.7
C2 C3 S1 104.46(19)
C2 C3 H3A 110.9
S1 C3 H3A 110.9
C2 C3 H3B 110.9
S1 C3 H3B 110.9
H3A C3 H3B 108.9
N1 C4 H4A 109.5
N1 C4 H4B 109.5
H4A C4 H4B 109.5
N1 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
C6 C5 C10 119.2(2)
C6 C5 C1 119.4(2)
C10 C5 C1 121.4(2)
C7 C6 C5 120.7(2)
C7 C6 H6 119.7
C5 C6 H6 119.7
C6 C7 C8 120.1(3)
C6 C7 H7 119.9
C8 C7 H7 119.9
C7 C8 C9 119.9(3)
C7 C8 H8 120.1
C9 C8 H8 120.1
C8 C9 C10 120.0(2)
C8 C9 H9 120.0
C10 C9 H9 120.0
C5 C10 C9 120.1(2)
C5 C10 H10 119.9
C9 C10 H10 119.9
C4 N1 C1 116.5(2)
C4 N1 S1 114.10(18)
C1 N1 S1 109.72(16)
O2 S1 O1 115.80(16)
O2 S1 N1 109.26(12)
O1 S1 N1 111.58(13)
O2 S1 C3 112.41(17)
O1 S1 C3 109.79(15)
N1 S1 C3 96.35(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.477(3)
C1 C5 1.509(3)
C1 C2 1.532(4)
C1 H1 1.0000
C2 C3 1.522(4)
C2 H2A 0.9900
C2 H2B 0.9900
C3 S1 1.790(3)
C3 H3A 0.9900
C3 H3B 0.9900
C4 N1 1.469(3)
C4 H4A 0.9800
C4 H4B 0.9800
C4 H4C 0.9800
C5 C6 1.390(4)
C5 C10 1.393(4)
C6 C7 1.384(4)
C6 H6 0.9500
C7 C8 1.384(4)
C7 H7 0.9500
C8 C9 1.388(4)
C8 H8 0.9500
C9 C10 1.394(4)
C9 H9 0.9500
C10 H10 0.9500
N1 S1 1.658(2)
O1 S1 1.439(2)
O2 S1 1.428(2)
