#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:07:05 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180466 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/35/7213529.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_7213529
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         'C13 H16 N2 O4'
_chemical_formula_structural     'C13 H16 N2 O4'
_chemical_formula_sum            'C14 H16 N2 O4'
_chemical_formula_weight         276.29
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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             2001-08-06T13:20:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 110.21(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.328(2)
_cell_length_b                   9.1873(9)
_cell_length_c                   13.049(3)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_measurement_wavelength     0.71073
_cell_volume                     1387.0(5)
_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      297(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_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      -0.11316E-1
_diffrn_orient_matrix_UB_12      0.107852
_diffrn_orient_matrix_UB_13      -0.5215E-2
_diffrn_orient_matrix_UB_21      0.08451
_diffrn_orient_matrix_UB_22      0.14451E-1
_diffrn_orient_matrix_UB_23      0.40123E-1
_diffrn_orient_matrix_UB_31      0.14164E-1
_diffrn_orient_matrix_UB_32      0.206E-3
_diffrn_orient_matrix_UB_33      -0.71023E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_av_unetI/netI     0.0875
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2423
_diffrn_reflns_theta_full        24.96
_diffrn_reflns_theta_max         24.96
_diffrn_reflns_theta_min         2.77
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        -2
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9806
_exptl_absorpt_correction_T_min  0.9526
_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   1
Theta correction was applied.
Averaged transmission function was used.
No Fourier smoothing was applied.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.1769
_refine_ls_R_factor_gt           0.0492
_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)+(0.0729P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1642
_reflns_number_gt                889
_reflns_number_total             2312
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b109624asup1.cif
_cod_data_source_block           cw1168
_cod_original_cell_volume        1387.0(4)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7213529
#BEGIN Tags that were not found in dictionaries:
_exptl_absorpt_factor_mur        0.02
_exptl_absorpt_correction_t_ave  0.9483
_diffrn_standards_decay_corr_max 1.001
_diffrn_standards_decay_corr_min 0.962
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.7395(4) 0.1276(4) 0.6331(3) 0.0693(11) Uani 1 1 d .
C4 C 0.9292(4) 0.1350(4) 0.6244(3) 0.0727(12) Uani 1 1 d .
C5 C 0.9708(4) 0.0844(4) 0.7354(3) 0.0620(10) Uani 1 1 d .
C6 C 0.8996(4) 0.1029(4) 0.8002(3) 0.0617(10) Uani 1 1 d .
C7 C 1.0856(4) 0.0266(4) 0.7827(3) 0.0645(11) Uani 1 1 d .
C8 C 1.2748(4) 0.0206(4) 0.7538(3) 0.0654(11) Uani 1 1 d .
C9 C 1.3265(5) -0.0524(4) 0.6898(3) 0.0794(12) Uani 1 1 d .
H9 H 1.2819 -0.1069 0.63 0.095 Uiso 1 1 calc R
C10 C 1.4434(5) -0.0436(5) 0.7151(4) 0.0891(14) Uani 1 1 d .
H10 H 1.4781 -0.093 0.6724 0.107 Uiso 1 1 calc R
C11 C 1.5107(5) 0.0371(5) 0.8028(4) 0.0915(14) Uani 1 1 d .
H11 H 1.5904 0.0423 0.8198 0.11 Uiso 1 1 calc R
C12 C 1.4582(4) 0.1096(5) 0.8645(4) 0.0884(13) Uani 1 1 d .
H12 H 1.5028 0.1639 0.9244 0.106 Uiso 1 1 calc R
C13 C 1.3418(4) 0.1033(4) 0.8396(3) 0.0780(12) Uani 1 1 d .
H13 H 1.3073 0.1555 0.8812 0.094 Uiso 1 1 calc R
C14 C 1.2150(4) -0.1254(5) 0.9327(3) 0.0916(15) Uani 1 1 d .
H14A H 1.2243 -0.1402 1.0081 0.137 Uiso 1 1 calc R
H14B H 1.2859 -0.0892 0.9274 0.137 Uiso 1 1 calc R
H14C H 1.1954 -0.2161 0.8942 0.137 Uiso 1 1 calc R
C21 C 0.7150(4) -0.0307(4) 0.6074(3) 0.0818(13) Uani 1 1 d .
H21A H 0.6815 -0.0433 0.5297 0.123 Uiso 1 1 calc R
H21B H 0.6621 -0.0652 0.6413 0.123 Uiso 1 1 calc R
H21C H 0.7858 -0.0849 0.6347 0.123 Uiso 1 1 calc R
C22 C 0.6355(4) 0.2230(5) 0.5949(4) 0.0967(15) Uani 1 1 d .
H22A H 0.5987 0.2127 0.5173 0.145 Uiso 1 1 calc R
H22B H 0.6583 0.3225 0.612 0.145 Uiso 1 1 calc R
H22C H 0.5824 0.1953 0.6306 0.145 Uiso 1 1 calc R
N1 N 1.1522(4) 0.0133(4) 0.7206(3) 0.0794(11) Uani 1 1 d .
N2 N 1.1237(3) -0.0212(4) 0.8852(3) 0.0673(10) Uani 1 1 d .
O1 O 0.7895(2) 0.1477(3) 0.74961(19) 0.0709(8) Uani 1 1 d .
O3 O 0.8184(3) 0.1822(3) 0.5841(2) 0.0768(8) Uani 1 1 d .
O4 O 0.9846(3) 0.1439(4) 0.5623(2) 0.1016(11) Uani 1 1 d .
O6 O 0.9300(2) 0.0885(3) 0.90023(19) 0.0708(8) Uani 1 1 d .
H1 H 1.117(3) 0.039(4) 0.655(4) 0.073(13) Uiso 1 1 d .
H2 H 1.077(3) -0.004(4) 0.915(3) 0.065(14) Uiso 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C2 0.083(3) 0.068(3) 0.048(2) 0.0037(18) 0.011(2) 0.002(2)
C4 0.097(4) 0.076(3) 0.038(2) 0.0088(18) 0.015(2) -0.001(2)
C5 0.082(3) 0.065(2) 0.037(2) 0.0027(16) 0.017(2) -0.002(2)
C6 0.075(3) 0.057(2) 0.044(2) 0.0004(17) 0.008(2) -0.002(2)
C7 0.087(3) 0.070(2) 0.037(2) -0.0009(17) 0.023(2) -0.007(2)
C8 0.081(3) 0.071(3) 0.044(2) 0.0045(18) 0.020(2) 0.005(2)
C9 0.105(4) 0.083(3) 0.059(3) -0.012(2) 0.039(3) -0.006(3)
C10 0.098(4) 0.102(3) 0.075(3) -0.014(3) 0.039(3) 0.013(3)
C11 0.082(3) 0.120(4) 0.075(3) -0.005(3) 0.031(3) 0.012(3)
C12 0.093(4) 0.110(3) 0.055(3) -0.014(2) 0.017(3) 0.012(3)
C13 0.085(3) 0.088(3) 0.061(3) -0.011(2) 0.025(2) 0.013(3)
C14 0.119(4) 0.105(3) 0.056(3) 0.029(2) 0.036(3) 0.036(3)
C21 0.093(4) 0.077(3) 0.059(3) -0.002(2) 0.006(2) -0.006(2)
C22 0.105(4) 0.096(3) 0.071(3) 0.014(2) 0.008(3) 0.029(3)
N1 0.086(3) 0.114(3) 0.036(2) 0.0052(18) 0.018(2) 0.003(2)
N2 0.080(3) 0.081(2) 0.0419(19) 0.0092(15) 0.0228(19) 0.010(2)
O1 0.082(2) 0.0772(17) 0.0462(16) 0.0009(12) 0.0137(14) 0.0140(14)
O3 0.095(2) 0.0753(18) 0.0502(16) 0.0175(13) 0.0118(16) 0.0050(16)
O4 0.125(3) 0.135(3) 0.0493(18) 0.0303(16) 0.0356(19) 0.016(2)
O6 0.0850(19) 0.0918(19) 0.0326(14) 0.0018(11) 0.0168(13) 0.0028(14)
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'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
6 1 1
2 -5 -1
4 0 -6
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O3 C2 O1 108.5(3)
O3 C2 C22 106.5(3)
O1 C2 C22 106.5(3)
O3 C2 C21 110.8(3)
O1 C2 C21 109.9(3)
C22 C2 C21 114.4(4)
O4 C4 O3 116.0(3)
O4 C4 C5 126.8(5)
O3 C4 C5 117.1(4)
C6 C5 C7 120.5(3)
C6 C5 C4 118.8(4)
C7 C5 C4 120.6(4)
O6 C6 O1 115.9(4)
O6 C6 C5 126.2(4)
O1 C6 C5 117.8(3)
N2 C7 N1 120.0(4)
N2 C7 C5 120.5(4)
N1 C7 C5 119.4(3)
C13 C8 C9 119.2(4)
C13 C8 N1 123.5(4)
C9 C8 N1 117.1(4)
C10 C9 C8 119.5(4)
C9 C10 C11 121.1(4)
C12 C11 C10 118.7(5)
C13 C12 C11 120.9(4)
C12 C13 C8 120.5(4)
C7 N1 C8 128.2(4)
C7 N2 C14 127.1(4)
C6 O1 C2 117.9(3)
C4 O3 C2 117.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C2 O3 1.428(5)
C2 O1 1.441(4)
C2 C22 1.490(5)
C2 C21 1.499(5)
C4 O4 1.229(5)
C4 O3 1.354(5)
C4 C5 1.438(5)
C5 C6 1.424(5)
C5 C7 1.436(5)
C6 O6 1.234(4)
C6 O1 1.353(4)
C7 N2 1.329(5)
C7 N1 1.344(5)
C8 C13 1.369(5)
C8 C9 1.386(5)
C8 N1 1.422(5)
C9 C10 1.365(6)
C10 C11 1.376(6)
C11 C12 1.367(6)
C12 C13 1.359(6)
C14 N2 1.444(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 C6 170.3(4)
O3 C4 C5 C6 -7.6(5)
O4 C4 C5 C7 -4.9(6)
O3 C4 C5 C7 177.2(3)
C7 C5 C6 O6 8.4(6)
C4 C5 C6 O6 -166.8(3)
C7 C5 C6 O1 -175.3(3)
C4 C5 C6 O1 9.5(5)
C6 C5 C7 N2 5.4(5)
C4 C5 C7 N2 -179.5(3)
C6 C5 C7 N1 -178.4(3)
C4 C5 C7 N1 -3.3(5)
C13 C8 C9 C10 1.8(6)
N1 C8 C9 C10 177.1(4)
C8 C9 C10 C11 -0.4(7)
C9 C10 C11 C12 -0.2(7)
C10 C11 C12 C13 -0.5(7)
C11 C12 C13 C8 1.9(7)
C9 C8 C13 C12 -2.5(6)
N1 C8 C13 C12 -177.5(4)
N2 C7 N1 C8 -33.3(6)
C5 C7 N1 C8 150.4(4)
C13 C8 N1 C7 -30.7(6)
C9 C8 N1 C7 154.2(4)
N1 C7 N2 C14 -19.8(6)
C5 C7 N2 C14 156.4(4)
O6 C6 O1 C2 -163.0(3)
C5 C6 O1 C2 20.3(5)
O3 C2 O1 C6 -49.2(4)
C22 C2 O1 C6 -163.5(3)
C21 C2 O1 C6 72.1(4)
O4 C4 O3 C2 157.4(3)
C5 C4 O3 C2 -24.5(5)
O1 C2 O3 C4 51.4(4)
C22 C2 O3 C4 165.7(3)
C21 C2 O3 C4 -69.4(4)
