#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:07:05 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180466 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/35/7213527.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_7213527
loop_
_publ_author_name
'Bernhardt, Paul V.'
'Koch, Rainer'
'Moloney, Daniel W. J.'
'Shtaiwi, Majed'
'Wentrup, Curt'
_publ_section_title
;
 Twisting and planarization in push--pull ethylenesElectronic
 supplementary information (ESI) available: tables of X-ray
 crystallographic bond lengths and angles of compounds 8--19 (including
 selected torsional angles and hydrogen bonds), X-ray crystal structures
 of compounds 10, 11, 13, 16, and 18 (Figs. S1--S5) and packing diagrams
 for 17·H2O and 19·H2O (Figs. S6--S7). See
 http://www.rsc.org/suppdata/p2/b1/b109624a/
;
_journal_issue                   3
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              515
_journal_paper_doi               10.1039/b109624a
_journal_year                    2002
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H23 N1 O4 S1'
_chemical_formula_structural     'C18 H23 N O4 S'
_chemical_formula_sum            'C18 H23 N O4 S'
_chemical_formula_weight         349.43
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_conform_dict_location     ftp://ftp.iucr.org/cifdics/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.1
_audit_creation_date             2001-08-06T13:06:33-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 97.630(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8985(9)
_cell_length_b                   8.4510(10)
_cell_length_c                   19.677(2)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_measurement_wavelength     0.71073
_cell_volume                     1796.3(3)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_orient_matrix_type
;
x-axis points to radiation source
the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      -0.6409E-2
_diffrn_orient_matrix_UB_12      0.14333E-1
_diffrn_orient_matrix_UB_13      0.49838E-1
_diffrn_orient_matrix_UB_21      0.3163E-2
_diffrn_orient_matrix_UB_22      -0.117307
_diffrn_orient_matrix_UB_23      0.6555E-2
_diffrn_orient_matrix_UB_31      0.92326E-1
_diffrn_orient_matrix_UB_32      0.5011E-2
_diffrn_orient_matrix_UB_33      0.01
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            3313
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         1.89
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        -3
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  0.9061
_exptl_absorpt_correction_T_min  0.8889
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Number of psi-scan sets used was   4
Theta correction was applied.
Averaged transmission function was used.
No Fourier smoothing was applied.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3135
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0522
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0976P)²+0.2451P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1366
_refine_ls_wR_factor_ref         0.1624
_reflns_number_gt                2025
_reflns_number_total             3135
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b109624asup1.cif
_cod_data_source_block           cw10187
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7213527
#BEGIN Tags that were not found in dictionaries:
_exptl_absorpt_factor_mur        0.101
_exptl_absorpt_correction_t_ave  0.817
_diffrn_standards_decay_corr_max 1.05
_diffrn_standards_decay_corr_min 0.87
#END Tags that were not found in dictionaries
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
C2 C 0.6167(3) 0.3404(4) 0.93817(13) 0.0438(7) Uani 1 1 d .
C4 C 0.4377(3) 0.4294(3) 0.86338(13) 0.0359(6) Uani 1 1 d .
C5 C 0.4498(2) 0.2850(3) 0.82548(13) 0.0350(6) Uani 1 1 d .
C6 C 0.5698(3) 0.2128(3) 0.82866(13) 0.0349(6) Uani 1 1 d .
C7 C 0.3479(3) 0.2319(3) 0.77895(14) 0.0371(6) Uani 1 1 d .
C8 C 0.3965(4) -0.0795(4) 0.82433(18) 0.0595(9) Uani 1 1 d .
H8A H 0.3845 -0.1901 0.8143 0.089 Uiso 1 1 calc R
H8B H 0.3628 -0.0543 0.8657 0.089 Uiso 1 1 calc R
H8C H 0.4834 -0.0557 0.8302 0.089 Uiso 1 1 calc R
C9 C 0.1430(3) 0.2923(4) 0.71515(16) 0.0455(7) Uani 1 1 d .
C10 C 0.0477(3) 0.2530(4) 0.75320(17) 0.0540(8) Uani 1 1 d .
C11 C -0.0665(3) 0.2190(5) 0.7170(2) 0.0662(10) Uani 1 1 d .
H11 H -0.1316 0.1915 0.7408 0.079 Uiso 1 1 calc R
C12 C -0.0862(3) 0.2248(5) 0.6467(2) 0.0724(11) Uani 1 1 d .
H12 H -0.1641 0.2018 0.6234 0.087 Uiso 1 1 calc R
C13 C 0.0087(3) 0.2645(5) 0.61111(19) 0.0664(10) Uani 1 1 d .
H13 H -0.0058 0.2676 0.5635 0.08 Uiso 1 1 calc R
C14 C 0.1252(3) 0.3001(4) 0.64356(16) 0.0489(8) Uani 1 1 d .
C15 C 0.0706(4) 0.2456(6) 0.8305(2) 0.0781(12) Uani 1 1 d .
H15A H 0.1001 0.1402 0.8436 0.094 Uiso 1 1 calc R
H15B H 0.1366 0.3191 0.8462 0.094 Uiso 1 1 calc R
C16 C -0.0322(4) 0.2800(9) 0.8660(2) 0.119(2) Uani 1 1 d .
H16A H -0.007 0.2721 0.9145 0.179 Uiso 1 1 calc R
H16B H -0.0976 0.2058 0.8525 0.179 Uiso 1 1 calc R
H16C H -0.0612 0.3853 0.8549 0.179 Uiso 1 1 calc R
C17 C 0.2330(3) 0.3437(5) 0.60562(17) 0.0623(10) Uani 1 1 d .
H17A H 0.2714 0.4387 0.6263 0.075 Uiso 1 1 calc R
H17B H 0.2939 0.2595 0.6125 0.075 Uiso 1 1 calc R
C18 C 0.2016(4) 0.3720(6) 0.5294(2) 0.0859(13) Uani 1 1 d .
H18A H 0.2757 0.3984 0.5104 0.129 Uiso 1 1 calc R
H18B H 0.1436 0.4576 0.5217 0.129 Uiso 1 1 calc R
H18C H 0.1658 0.2779 0.5078 0.129 Uiso 1 1 calc R
C21 C 0.5546(4) 0.2303(4) 0.98311(16) 0.0608(9) Uani 1 1 d .
H21A H 0.5291 0.2886 1.0207 0.091 Uiso 1 1 calc R
H21B H 0.6115 0.1487 1.0005 0.091 Uiso 1 1 calc R
H21C H 0.4834 0.1832 0.9568 0.091 Uiso 1 1 calc R
C22 C 0.7308(3) 0.4180(5) 0.97472(18) 0.0663(10) Uani 1 1 d .
H22A H 0.7097 0.4758 1.0136 0.099 Uiso 1 1 calc R
H22B H 0.7644 0.4893 0.944 0.099 Uiso 1 1 calc R
H22C H 0.7911 0.3385 0.99 0.099 Uiso 1 1 calc R
N1 N 0.2627(2) 0.3322(3) 0.75109(13) 0.0453(6) Uani 1 1 d .
O1 O 0.65658(17) 0.2566(2) 0.88133(9) 0.0435(5) Uani 1 1 d .
O3 O 0.53496(18) 0.4648(2) 0.91271(9) 0.0425(5) Uani 1 1 d .
O4 O 0.35294(19) 0.5224(2) 0.85659(10) 0.0441(5) Uani 1 1 d .
O6 O 0.60347(18) 0.1227(3) 0.78694(9) 0.0461(5) Uani 1 1 d .
S1 S 0.31967(8) 0.03483(10) 0.75511(4) 0.0504(3) Uani 1 1 d .
H1 H 0.279(3) 0.440(5) 0.7579(18) 0.070(12) Uiso 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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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 0.006 '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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-1 -1 11
6 -2 -2
6 1 -5
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O3 C2 O1 109.2(2)
O3 C2 C22 106.6(3)
O1 C2 C22 105.7(3)
O3 C2 C21 110.7(3)
O1 C2 C21 111.0(3)
C22 C2 C21 113.4(3)
O4 C4 O3 116.4(2)
O4 C4 C5 127.9(2)
O3 C4 C5 115.7(2)
C7 C5 C6 121.7(3)
C7 C5 C4 118.9(2)
C6 C5 C4 118.7(2)
O6 C6 O1 116.5(2)
O6 C6 C5 126.4(2)
O1 C6 C5 117.1(2)
N1 C7 C5 120.9(3)
N1 C7 S1 114.3(2)
C5 C7 S1 124.8(2)
C14 C9 C10 122.5(3)
C14 C9 N1 118.7(3)
C10 C9 N1 118.8(3)
C11 C10 C9 117.1(3)
C11 C10 C15 121.9(3)
C9 C10 C15 121.0(3)
C12 C11 C10 121.5(3)
C13 C12 C11 119.8(3)
C12 C13 C14 122.0(3)
C13 C14 C9 116.9(3)
C13 C14 C17 123.4(3)
C9 C14 C17 119.6(3)
C16 C15 C10 116.7(4)
C18 C17 C14 116.0(3)
C7 N1 C9 126.5(3)
C6 O1 C2 118.4(2)
C4 O3 C2 118.5(2)
C7 S1 C8 105.27(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2 O3 1.425(3)
C2 O1 1.439(3)
C2 C22 1.502(5)
C2 C21 1.506(5)
C4 O4 1.207(3)
C4 O3 1.372(3)
C4 C5 1.445(4)
C5 C7 1.416(4)
C5 C6 1.437(4)
C6 O6 1.212(3)
C6 O1 1.358(3)
C7 N1 1.321(4)
C7 S1 1.747(3)
C8 S1 1.785(3)
C9 C14 1.398(4)
C9 C10 1.398(5)
C9 N1 1.438(4)
C10 C11 1.380(5)
C10 C15 1.509(5)
C11 C12 1.371(5)
C12 C13 1.366(6)
C13 C14 1.377(4)
C14 C17 1.518(5)
C15 C16 1.427(6)
C17 C18 1.511(5)
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
O4 C4 C5 C7 -7.1(4)
O3 C4 C5 C7 173.3(2)
O4 C4 C5 C6 163.9(3)
O3 C4 C5 C6 -15.7(4)
C7 C5 C6 O6 13.3(5)
C4 C5 C6 O6 -157.4(3)
C7 C5 C6 O1 -170.8(3)
C4 C5 C6 O1 18.5(4)
C6 C5 C7 N1 -146.1(3)
C4 C5 C7 N1 24.6(4)
C6 C5 C7 S1 35.8(4)
C4 C5 C7 S1 -153.5(2)
C14 C9 C10 C11 1.0(5)
N1 C9 C10 C11 178.5(3)
C14 C9 C10 C15 179.9(3)
N1 C9 C10 C15 -2.6(5)
C9 C10 C11 C12 -0.6(6)
C15 C10 C11 C12 -179.5(4)
C10 C11 C12 C13 0.2(7)
C11 C12 C13 C14 -0.3(7)
C12 C13 C14 C9 0.6(6)
C12 C13 C14 C17 179.6(4)
C10 C9 C14 C13 -1.0(5)
N1 C9 C14 C13 -178.5(3)
C10 C9 C14 C17 180.0(3)
N1 C9 C14 C17 2.4(5)
C11 C10 C15 C16 -30.2(7)
C9 C10 C15 C16 150.9(5)
C13 C14 C17 C18 9.4(6)
C9 C14 C17 C18 -171.6(4)
C5 C7 N1 C9 -166.0(3)
S1 C7 N1 C9 12.2(4)
C14 C9 N1 C7 -103.0(4)
C10 C9 N1 C7 79.4(4)
O6 C6 O1 C2 -169.3(2)
C5 C6 O1 C2 14.4(4)
O3 C2 O1 C6 -47.3(3)
C22 C2 O1 C6 -161.6(3)
C21 C2 O1 C6 75.0(3)
O4 C4 O3 C2 160.2(2)
C5 C4 O3 C2 -20.1(3)
O1 C2 O3 C4 50.4(3)
C22 C2 O3 C4 164.2(2)
C21 C2 O3 C4 -72.1(3)
N1 C7 S1 C8 -153.6(2)
C5 C7 S1 C8 24.5(3)
