#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/72/2207249.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2207249
loop_
_publ_author_name
'Chen, Yong-Jiang'
'Xu, Gang'
'Cui, Yu-Bo'
'Huang, Wei'
'Gou, Shao-Hua'
_publ_section_title
;
 1-(p-Tolylsulfonyl)-<small>L</small>-proline ethyl ester
;
_journal_coeditor_code           HG6251
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3571
_journal_page_last               o3573
_journal_paper_doi               10.1107/S1600536805031636
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C14 H19 N O4 S'
_chemical_formula_moiety         'C14 H19 N O4 S'
_chemical_formula_sum            'C14 H19 N O4 S'
_chemical_formula_weight         297.36
_chemical_name_systematic
;
L-1-(p-Tolylsulfonyl)proline ethyl ester
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4671(17)
_cell_length_b                   11.547(3)
_cell_length_c                   17.445(4)
_cell_measurement_reflns_used    784
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      25.09
_cell_measurement_theta_min      3.00
_cell_volume                     1504.2(6)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0687
_diffrn_reflns_av_sigmaI/netI    0.0781
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7523
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.12
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.9146
_exptl_absorpt_correction_T_min  0.8757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.151
_refine_ls_abs_structure_details 'Flack (1983), 1104 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.08(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2652
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      0.930
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.024P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0812
_refine_ls_wR_factor_ref         0.0880
_reflns_number_gt                1855
_reflns_number_total             2652
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg6251.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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_cell_volume        1504.1(6)
_cod_database_code               2207249
_cod_database_fobs_code          2207249
loop_
_symmetry_equiv_pos_as_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'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
C1 0.4766(4) 0.6102(3) 0.29772(16) 0.0449(7) Uani d . 1 C
C2 0.4520(4) 0.5131(3) 0.34185(18) 0.0556(9) Uani d . 1 C
H2 0.4522 0.4402 0.3192 0.067 Uiso calc R 1 H
C3 0.4269(4) 0.5239(3) 0.4194(2) 0.0635(11) Uani d . 1 C
H3 0.4116 0.4576 0.4490 0.076 Uiso calc R 1 H
C4 0.4240(5) 0.6301(4) 0.45421(19) 0.0641(11) Uani d . 1 C
C5 0.4469(5) 0.7256(3) 0.4092(2) 0.0719(11) Uani d . 1 C
H5 0.4449 0.7985 0.4320 0.086 Uiso calc R 1 H
C6 0.4728(5) 0.7178(3) 0.33139(17) 0.0582(9) Uani d . 1 C
H6 0.4874 0.7843 0.3019 0.070 Uiso calc R 1 H
C7 0.4010(6) 0.6413(4) 0.54008(17) 0.1057(16) Uani d . 1 C
H7A 0.3267 0.5794 0.5585 0.159 Uiso calc R 1 H
H7B 0.3456 0.7142 0.5517 0.159 Uiso calc R 1 H
H7C 0.5160 0.6373 0.5645 0.159 Uiso calc R 1 H
C8 0.8309(4) 0.4890(3) 0.2233(2) 0.0629(10) Uani d . 1 C
H8A 0.8325 0.4253 0.1871 0.075 Uiso calc R 1 H
H8B 0.7743 0.4632 0.2704 0.075 Uiso calc R 1 H
C9 1.0178(5) 0.5330(3) 0.2385(2) 0.0746(11) Uani d . 1 C
H9A 1.0954 0.5188 0.1949 0.090 Uiso calc R 1 H
H9B 1.0689 0.4964 0.2835 0.090 Uiso calc R 1 H
C10 0.9911(5) 0.6622(3) 0.25129(17) 0.0717(10) Uani d . 1 C
H10A 0.9521 0.6778 0.3033 0.086 Uiso calc R 1 H
H10B 1.1009 0.7047 0.2415 0.086 Uiso calc R 1 H
C11 0.8473(4) 0.6946(3) 0.19404(17) 0.0516(9) Uani d . 1 C
H11 0.7779 0.7613 0.2120 0.062 Uiso calc R 1 H
C12 0.9287(5) 0.7183(3) 0.11713(18) 0.0553(9) Uani d . 1 C
C13 1.0765(7) 0.8578(4) 0.0413(2) 0.1163(17) Uani d DU 1 C
H13A 1.1955 0.8241 0.0425 0.140 Uiso calc R 1 H
H13B 1.0139 0.8274 -0.0031 0.140 Uiso calc R 1 H
C14 1.0899(5) 0.9825(4) 0.0356(2) 0.0970(15) Uani d D 1 C
H14A 1.1452 1.0126 0.0811 0.145 Uiso calc R 1 H
H14B 0.9723 1.0150 0.0302 0.145 Uiso calc R 1 H
H14C 1.1610 1.0026 -0.0082 0.145 Uiso calc R 1 H
N1 0.7360(3) 0.5908(2) 0.19090(13) 0.0522(6) Uani d . 1 N
O1 0.4515(3) 0.49069(19) 0.17390(11) 0.0628(7) Uani d . 1 O
O2 0.4681(4) 0.70389(19) 0.16354(11) 0.0652(7) Uani d . 1 O
O3 0.9798(4) 0.8272(2) 0.11091(12) 0.0816(8) Uani d U 1 O
O4 0.9485(4) 0.6479(2) 0.06845(12) 0.0881(9) Uani d . 1 O
S1 0.52168(11) 0.59891(7) 0.19946(4) 0.0508(2) Uani d . 1 S
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
_geom_angle_publ_flag
C2 C1 C6 119.7(3) ?
C2 C1 S1 121.0(2) ?
C6 C1 S1 119.3(2) ?
C3 C2 C1 119.9(3) ?
C3 C2 H2 120.1 ?
C1 C2 H2 120.1 ?
C4 C3 C2 121.4(3) ?
C4 C3 H3 119.3 ?
C2 C3 H3 119.3 ?
C5 C4 C3 117.9(3) ?
C5 C4 C7 121.0(4) ?
C3 C4 C7 121.1(4) ?
C4 C5 C6 122.2(3) ?
C4 C5 H5 118.9 ?
C6 C5 H5 118.9 ?
C5 C6 C1 119.0(3) ?
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 ?
N1 C8 C9 103.9(3) ?
N1 C8 H8A 111.0 ?
C9 C8 H8A 111.0 ?
N1 C8 H8B 111.0 ?
C9 C8 H8B 111.0 ?
H8A C8 H8B 109.0 ?
C8 C9 C10 103.6(3) ?
C8 C9 H9A 111.0 ?
C10 C9 H9A 111.0 ?
C8 C9 H9B 111.0 ?
C10 C9 H9B 111.0 ?
H9A C9 H9B 109.0 ?
C11 C10 C9 103.7(3) ?
C11 C10 H10A 111.0 ?
C9 C10 H10A 111.0 ?
C11 C10 H10B 111.0 ?
C9 C10 H10B 111.0 ?
H10A C10 H10B 109.0 ?
N1 C11 C12 110.3(3) ?
N1 C11 C10 103.1(3) ?
C12 C11 C10 110.4(3) ?
N1 C11 H11 110.9 ?
C12 C11 H11 110.9 ?
C10 C11 H11 110.9 ?
O4 C12 O3 124.0(3) ?
O4 C12 C11 124.6(3) ?
O3 C12 C11 111.4(3) ?
C14 C13 O3 109.5(3) ?
C14 C13 H13A 109.8 ?
O3 C13 H13A 109.8 ?
C14 C13 H13B 109.8 ?
O3 C13 H13B 109.8 ?
H13A C13 H13B 108.2 ?
C13 C14 H14A 109.5 ?
C13 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
C13 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
C11 N1 C8 111.4(2) y
C11 N1 S1 121.0(2) y
C8 N1 S1 119.0(2) y
C12 O3 C13 116.4(3) ?
O2 S1 O1 120.37(13) y
O2 S1 N1 106.77(15) y
O1 S1 N1 106.57(14) y
O2 S1 C1 108.30(14) y
O1 S1 C1 107.48(14) y
N1 S1 C1 106.61(12) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.372(4) ?
C1 C6 1.375(4) ?
C1 S1 1.752(3) y
C2 C3 1.372(4) ?
C2 H2 0.9300 ?
C3 C4 1.368(5) ?
C3 H3 0.9300 ?
C4 C5 1.365(4) ?
C4 C7 1.513(4) ?
C5 C6 1.374(4) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C7 H7A 0.9600 ?
C7 H7B 0.9600 ?
C7 H7C 0.9600 ?
C8 N1 1.485(4) y
C8 C9 1.509(5) ?
C8 H8A 0.9700 ?
C8 H8B 0.9700 ?
C9 C10 1.522(4) ?
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10 C11 1.514(4) ?
C10 H10A 0.9700 ?
C10 H10B 0.9700 ?
C11 N1 1.459(4) y
C11 C12 1.498(4) ?
C11 H11 0.9800 ?
C12 O4 1.185(3) y
C12 O3 1.318(4) y
C13 C14 1.446(4) ?
C13 O3 1.456(4) y
C13 H13A 0.9700 ?
C13 H13B 0.9700 ?
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 0.9600 ?
N1 S1 1.610(2) y
O1 S1 1.426(2) y
O2 S1 1.422(2) y
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C6 H6 O2 . 0.93 2.59 2.933(4) 102
C11 H11 O2 . 0.98 2.55 2.883(4) 100
C6 H6 O1 3_655 0.93 2.46 3.202(4) 137
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 C3 -1.2(5)
S1 C1 C2 C3 176.3(2)
C1 C2 C3 C4 0.7(5)
C2 C3 C4 C5 0.0(6)
C2 C3 C4 C7 -178.5(3)
C3 C4 C5 C6 -0.2(6)
C7 C4 C5 C6 178.3(4)
C4 C5 C6 C1 -0.3(6)
C2 C1 C6 C5 1.0(5)
S1 C1 C6 C5 -176.5(3)
N1 C8 C9 C10 27.1(3)
C8 C9 C10 C11 -37.9(3)
C9 C10 C11 N1 33.4(3)
C9 C10 C11 C12 -84.4(4)
N1 C11 C12 O4 -22.0(5)
C10 C11 C12 O4 91.3(4)
N1 C11 C12 O3 159.6(3)
C10 C11 C12 O3 -87.1(4)
C12 C11 N1 C8 100.9(3)
C10 C11 N1 C8 -16.9(3)
C12 C11 N1 S1 -111.7(3)
C10 C11 N1 S1 130.5(2)
C9 C8 N1 C11 -6.5(3)
C9 C8 N1 S1 -154.6(2)
O4 C12 O3 C13 -4.1(6)
C11 C12 O3 C13 174.3(3)
C14 C13 O3 C12 168.1(4)
C11 N1 S1 O2 35.1(3)
C8 N1 S1 O2 -179.9(2)
C11 N1 S1 O1 164.9(2)
C8 N1 S1 O1 -50.1(3)
C11 N1 S1 C1 -80.5(2)
C8 N1 S1 C1 64.5(3)
C2 C1 S1 O2 156.1(3)
C6 C1 S1 O2 -26.4(3)
C2 C1 S1 O1 24.6(3)
C6 C1 S1 O1 -157.9(3)
C2 C1 S1 N1 -89.4(3)
C6 C1 S1 N1 88.2(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21180127
