##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'SHELXL-97'
_journal_date_recd_electronic     2007-12-18
_journal_date_accepted     2008-01-02
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      2
_journal_page_first     o385
_journal_page_last     o385
_journal_paper_category     QO
_journal_coeditor_code     CI2549
_publ_contact_author_name     'Zheng, Hu'
_publ_contact_author_address
;
Department of Medicinal Chemistry,
West China School of Pharmacy,
Sichuan University,
Chengdu, 610041
People's Republic of China
;
_publ_contact_author_email     wcums416@yahoo.com.cn
_publ_contact_author_fax     '86-28-85501609'
_publ_contact_author_phone     '86-28-85501609'
_publ_section_title
;
trans-4-Nitrophenyl 4-(tosyloxymethyl)cyclohexanecarboxylate
;
loop_
    _publ_author_name
    _publ_author_address
    'Qi, Qing-Rong'
;
     Department of Medicinal Chemistry
     West China School of Pharmacy
     Sichuan University
     Chengdu 610041
     People's Republic of China
;
    'Huang, Wen-Cai'
;
     Department of Pharmaceutical and Bioengineering
     School of Chemical Engineering
     Sichuan University
     Chengdu 610065
     People's Republic of China
;
    'Mao, Zhi-Hua'
;
     The Center for Testing and Analysis
     Sichuan University
     Chengdu 610064
     People's Republic of China
;
    'Zheng, Hu'
;
     Department of Medicinal Chemistry
     West China School of Pharmacy
     Sichuan University
     Chengdu 610041
     People's Republic of China
;
data_I
_chemical_name_systematic
;
trans-4-Nitrophenyl 4-(tosyloxymethyl)cyclohexanecarboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H23 N O7 S'
_chemical_formula_sum     'C21 H23 N O7 S'
_chemical_formula_iupac     'C21 H23 N O7 S'
_chemical_formula_weight     433.46
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     20.499(5)
_cell_length_b     6.111(3)
_cell_length_c     17.250(4)
_cell_angle_alpha     90.00
_cell_angle_beta     102.04(3)
_cell_angle_gamma     90.00
_cell_volume     2113.4(13)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     33
_cell_measurement_theta_min     4.50
_cell_measurement_theta_max     7.55
_cell_measurement_temperature     292(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.38
_exptl_crystal_size_min     0.30
_exptl_crystal_density_diffrn     1.362
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     912
_exptl_absorpt_coefficient_mu     0.196
_exptl_absorpt_correction_type     none
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     292(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Enraf--Nonius CAD-4'
_diffrn_measurement_method     ω/2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4094
_diffrn_reflns_av_R_equivalents     0.0039
_diffrn_reflns_av_sigmaI/netI     0.0661
_diffrn_reflns_theta_min     1.02
_diffrn_reflns_theta_max     25.01
_diffrn_reflns_theta_full     25.01
_diffrn_measured_fraction_theta_max     0.987
_diffrn_measured_fraction_theta_full     0.987
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     24
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     0
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     3
_diffrn_standards_interval_count     300
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     2.072
_refine_special_details
;
  Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3627
_reflns_number_gt     1850
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1455
_refine_ls_R_factor_gt     0.0599
_refine_ls_wR_factor_gt     0.1552
_refine_ls_wR_factor_ref     0.1908
_refine_ls_goodness_of_fit_ref     1.059
_refine_ls_restrained_S_all     1.059
_refine_ls_number_reflns     3627
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0970P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     <0.001
_refine_diff_density_max     0.401
_refine_diff_density_min     -0.526
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'DIFRAC (Gabe & White, 1993)'
_computing_cell_refinement     'DIFRAC (Gabe & White, 1993)'
_computing_data_reduction     'NRCVAX (Gabe et al., 1989)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
loop_
    _atom_site_type_symbol
    _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_disorder_assembly
    _atom_site_disorder_group
    S S1 0.30112(5) -0.15510(18) 0.17299(7) 0.0556(4) Uani d . 1 . .
    O O1 0.30040(14) -0.0770(6) 0.09454(16) 0.0702(9) Uani d . 1 . .
    O O2 0.30099(14) -0.3830(5) 0.1871(2) 0.0763(10) Uani d . 1 . .
    O O3 0.23652(12) -0.0742(5) 0.19982(18) 0.0632(8) Uani d . 1 . .
    O O4 -0.09447(15) 0.2718(6) 0.1532(2) 0.0885(12) Uani d . 1 . .
    O O5 -0.08914(13) 0.5252(5) 0.06303(18) 0.0686(9) Uani d . 1 . .
    O O6 -0.39478(15) 0.7233(6) -0.0126(2) 0.0813(11) Uani d . 1 . .
    O O7 -0.36075(17) 0.9887(7) 0.0674(2) 0.0936(12) Uani d . 1 . .
    N N1 -0.35100(18) 0.8235(8) 0.0323(2) 0.0635(10) Uani d . 1 . .
    C C1 0.39156(18) 0.1686(7) 0.2212(2) 0.0500(10) Uani d . 1 . .
    H H1 0.3740 0.2367 0.1732 0.060 Uiso calc R 1 . .
    C C2 0.44258(19) 0.2665(7) 0.2753(2) 0.0536(11) Uani d . 1 . .
    H H2 0.4589 0.4016 0.2633 0.064 Uiso calc R 1 . .
    C C3 0.46966(18) 0.1673(8) 0.3465(2) 0.0526(10) Uani d . 1 . .
    C C4 0.4444(2) -0.0304(9) 0.3636(3) 0.0650(13) Uani d . 1 . .
    H H4 0.4618 -0.0973 0.4119 0.078 Uiso calc R 1 . .
    C C5 0.3931(2) -0.1337(8) 0.3100(2) 0.0593(12) Uani d . 1 . .
    H H5 0.3769 -0.2690 0.3220 0.071 Uiso calc R 1 . .
    C C6 0.36691(17) -0.0320(6) 0.2393(2) 0.0440(9) Uani d . 1 . .
    C C7 0.5248(2) 0.2787(10) 0.4050(3) 0.0811(16) Uani d . 1 . .
    H H7A 0.5125 0.4279 0.4121 0.122 Uiso calc R 1 . .
    H H7B 0.5652 0.2753 0.3852 0.122 Uiso calc R 1 . .
    H H7C 0.5316 0.2037 0.4550 0.122 Uiso calc R 1 . .
    C C8 0.21871(19) 0.1584(7) 0.1883(3) 0.0657(12) Uani d . 1 . .
    H H8A 0.2286 0.2104 0.1389 0.079 Uiso calc R 1 . .
    H H8B 0.2442 0.2448 0.2313 0.079 Uiso calc R 1 . .
    C C9 0.14546(17) 0.1807(7) 0.1864(2) 0.0507(10) Uani d . 1 . .
    H H9 0.1370 0.1230 0.2364 0.061 Uiso calc R 1 . .
    C C10 0.10207(18) 0.0551(7) 0.1192(2) 0.0527(10) Uani d . 1 . .
    H H10A 0.1131 -0.0992 0.1249 0.063 Uiso calc R 1 . .
    H H10B 0.1115 0.1046 0.0692 0.063 Uiso calc R 1 . .
    C C11 0.02817(18) 0.0850(8) 0.1176(2) 0.0564(11) Uani d . 1 . .
    H H11A 0.0178 0.0238 0.1655 0.068 Uiso calc R 1 . .
    H H11B 0.0023 0.0067 0.0726 0.068 Uiso calc R 1 . .
    C C12 0.00917(18) 0.3266(7) 0.1115(2) 0.0525(11) Uani d . 1 . .
    H H12 0.0175 0.3836 0.0614 0.063 Uiso calc R 1 . .
    C C13 0.05248(19) 0.4533(7) 0.1792(3) 0.0614(12) Uani d . 1 . .
    H H13A 0.0426 0.4050 0.2291 0.074 Uiso calc R 1 . .
    H H13B 0.0418 0.6078 0.1732 0.074 Uiso calc R 1 . .
    C C14 0.1265(2) 0.4210(7) 0.1814(3) 0.0648(12) Uani d . 1 . .
    H H14A 0.1374 0.4839 0.1340 0.078 Uiso calc R 1 . .
    H H14B 0.1523 0.4975 0.2269 0.078 Uiso calc R 1 . .
    C C15 -0.0628(2) 0.3620(8) 0.1128(2) 0.0545(11) Uani d . 1 . .
    C C16 -0.1560(2) 0.5894(8) 0.0600(2) 0.0574(12) Uani d . 1 . .
    C C17 -0.2075(2) 0.4605(8) 0.0214(3) 0.0662(13) Uani d . 1 . .
    H H17 -0.1994 0.3249 0.0008 0.079 Uiso calc R 1 . .
    C C18 -0.2720(2) 0.5386(8) 0.0140(3) 0.0631(13) Uani d . 1 . .
    H H18 -0.3080 0.4554 -0.0120 0.076 Uiso calc R 1 . .
    C C19 -0.28246(19) 0.7380(8) 0.0449(2) 0.0509(10) Uani d . 1 . .
    C C20 -0.2310(2) 0.8667(8) 0.0847(2) 0.0623(12) Uani d . 1 . .
    H H20 -0.2392 1.0013 0.1059 0.075 Uiso calc R 1 . .
    C C21 -0.1658(2) 0.7874(9) 0.0920(3) 0.0665(13) Uani d . 1 . .
    H H21 -0.1297 0.8690 0.1185 0.080 Uiso calc R 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    S1 O2 . 1.414(3) ?
    S1 O1 . 1.432(3) ?
    S1 O3 . 1.571(3) ?
    S1 C6 . 1.747(4) ?
    O3 C8 . 1.471(5) ?
    O4 C15 . 1.184(5) ?
    O5 C15 . 1.353(5) ?
    O5 C16 . 1.416(5) ?
    O6 N1 . 1.221(5) ?
    O7 N1 . 1.214(5) ?
    N1 C19 . 1.472(5) ?
    C1 C2 . 1.383(5) ?
    C1 C6 . 1.386(6) ?
    C1 H1 . 0.93 ?
    C2 C3 . 1.379(6) ?
    C2 H2 . 0.93 ?
    C3 C4 . 1.371(6) ?
    C3 C7 . 1.511(6) ?
    C4 C5 . 1.399(6) ?
    C4 H4 . 0.93 ?
    C5 C6 . 1.373(5) ?
    C5 H5 . 0.93 ?
    C7 H7A . 0.96 ?
    C7 H7B . 0.96 ?
    C7 H7C . 0.96 ?
    C8 C9 . 1.501(5) ?
    C8 H8A . 0.97 ?
    C8 H8B . 0.97 ?
    C9 C10 . 1.515(5) ?
    C9 C14 . 1.517(6) ?
    C9 H9 . 0.98 ?
    C10 C11 . 1.520(5) ?
    C10 H10A . 0.97 ?
    C10 H10B . 0.97 ?
    C11 C12 . 1.525(6) ?
    C11 H11A . 0.97 ?
    C11 H11B . 0.97 ?
    C12 C15 . 1.495(5) ?
    C12 C13 . 1.523(6) ?
    C12 H12 . 0.98 ?
    C13 C14 . 1.523(5) ?
    C13 H13A . 0.97 ?
    C13 H13B . 0.97 ?
    C14 H14A . 0.97 ?
    C14 H14B . 0.97 ?
    C16 C21 . 1.362(6) ?
    C16 C17 . 1.374(6) ?
    C17 C18 . 1.386(6) ?
    C17 H17 . 0.93 ?
    C18 C19 . 1.365(6) ?
    C18 H18 . 0.93 ?
    C19 C20 . 1.379(6) ?
    C20 C21 . 1.402(6) ?
    C20 H20 . 0.93 ?
    C21 H21 . 0.93 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O2 S1 O1 . . 119.4(2) ?
    O2 S1 O3 . . 103.13(18) ?
    O1 S1 O3 . . 109.29(18) ?
    O2 S1 C6 . . 109.87(18) ?
    O1 S1 C6 . . 109.28(19) ?
    O3 S1 C6 . . 104.74(18) ?
    C8 O3 S1 . . 117.7(3) ?
    C15 O5 C16 . . 118.9(3) ?
    O7 N1 O6 . . 123.9(4) ?
    O7 N1 C19 . . 118.2(4) ?
    O6 N1 C19 . . 117.9(4) ?
    C2 C1 C6 . . 119.4(4) ?
    C2 C1 H1 . . 120.3 ?
    C6 C1 H1 . . 120.3 ?
    C3 C2 C1 . . 121.2(4) ?
    C3 C2 H2 . . 119.4 ?
    C1 C2 H2 . . 119.4 ?
    C4 C3 C2 . . 118.6(4) ?
    C4 C3 C7 . . 121.1(4) ?
    C2 C3 C7 . . 120.2(4) ?
    C3 C4 C5 . . 121.4(4) ?
    C3 C4 H4 . . 119.3 ?
    C5 C4 H4 . . 119.3 ?
    C6 C5 C4 . . 118.9(4) ?
    C6 C5 H5 . . 120.5 ?
    C4 C5 H5 . . 120.5 ?
    C5 C6 C1 . . 120.4(4) ?
    C5 C6 S1 . . 119.5(3) ?
    C1 C6 S1 . . 120.1(3) ?
    C3 C7 H7A . . 109.5 ?
    C3 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    C3 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    O3 C8 C9 . . 108.0(3) ?
    O3 C8 H8A . . 110.1 ?
    C9 C8 H8A . . 110.1 ?
    O3 C8 H8B . . 110.1 ?
    C9 C8 H8B . . 110.1 ?
    H8A C8 H8B . . 108.4 ?
    C8 C9 C10 . . 113.3(4) ?
    C8 C9 C14 . . 109.4(3) ?
    C10 C9 C14 . . 110.1(3) ?
    C8 C9 H9 . . 107.9 ?
    C10 C9 H9 . . 107.9 ?
    C14 C9 H9 . . 107.9 ?
    C9 C10 C11 . . 112.2(3) ?
    C9 C10 H10A . . 109.2 ?
    C11 C10 H10A . . 109.2 ?
    C9 C10 H10B . . 109.2 ?
    C11 C10 H10B . . 109.2 ?
    H10A C10 H10B . . 107.9 ?
    C10 C11 C12 . . 110.9(3) ?
    C10 C11 H11A . . 109.5 ?
    C12 C11 H11A . . 109.5 ?
    C10 C11 H11B . . 109.5 ?
    C12 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 108.0 ?
    C15 C12 C13 . . 109.5(3) ?
    C15 C12 C11 . . 112.2(4) ?
    C13 C12 C11 . . 109.9(3) ?
    C15 C12 H12 . . 108.4 ?
    C13 C12 H12 . . 108.4 ?
    C11 C12 H12 . . 108.4 ?
    C12 C13 C14 . . 111.8(4) ?
    C12 C13 H13A . . 109.3 ?
    C14 C13 H13A . . 109.3 ?
    C12 C13 H13B . . 109.3 ?
    C14 C13 H13B . . 109.3 ?
    H13A C13 H13B . . 107.9 ?
    C9 C14 C13 . . 111.6(3) ?
    C9 C14 H14A . . 109.3 ?
    C13 C14 H14A . . 109.3 ?
    C9 C14 H14B . . 109.3 ?
    C13 C14 H14B . . 109.3 ?
    H14A C14 H14B . . 108.0 ?
    O4 C15 O5 . . 121.4(4) ?
    O4 C15 C12 . . 127.3(4) ?
    O5 C15 C12 . . 111.2(4) ?
    C21 C16 C17 . . 122.9(4) ?
    C21 C16 O5 . . 117.0(4) ?
    C17 C16 O5 . . 120.0(4) ?
    C16 C17 C18 . . 118.0(5) ?
    C16 C17 H17 . . 121.0 ?
    C18 C17 H17 . . 121.0 ?
    C19 C18 C17 . . 119.7(4) ?
    C19 C18 H18 . . 120.1 ?
    C17 C18 H18 . . 120.1 ?
    C18 C19 C20 . . 122.6(4) ?
    C18 C19 N1 . . 118.8(4) ?
    C20 C19 N1 . . 118.6(4) ?
    C19 C20 C21 . . 117.6(5) ?
    C19 C20 H20 . . 121.2 ?
    C21 C20 H20 . . 121.2 ?
    C16 C21 C20 . . 119.3(4) ?
    C16 C21 H21 . . 120.4 ?
    C20 C21 H21 . . 120.4 ?
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
    C5 H5 O7 2_535 0.93 2.49 3.290(6) 144
