#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:17:52 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180386 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/55/7205585.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_7205585
loop_
_publ_author_name
'Kole, Goutam Kumar'
'Tan, Geok Kheng'
'Vittal, Jagadese J.'
_publ_section_title
;
 Crystal engineering studies on the salts of
 trans-4,4′-stilbenedicarboxylic acid in the context of solid
 state [2 + 2] cycloaddition reaction
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              3138
_journal_paper_doi               10.1039/c0ce00224k
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C20 H28 N2 O6'
_chemical_formula_weight         392.44
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                100.688(2)
_cell_angle_beta                 96.117(3)
_cell_angle_gamma                90.070(3)
_cell_formula_units_Z            2
_cell_length_a                   7.4542(13)
_cell_length_b                   9.7070(16)
_cell_length_c                   13.610(2)
_cell_measurement_reflns_used    3326
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.24
_cell_measurement_theta_min      2.85
_cell_volume                     962.0(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12348
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.53
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_correction_T_min  0.9278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2005)'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.76
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4407
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0629
_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)+(0.0916P)²+0.5227P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1722
_refine_ls_wR_factor_ref         0.1790
_reflns_number_gt                3637
_reflns_number_total             4407
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ce00224k.txt
_cod_data_source_block           compound_4
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'Not Measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7205585
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4448(2) 0.72566(18) 0.33975(13) 0.0235(4) Uani 1 1 d . . .
H1A H 0.3776 0.6460 0.3267 0.035 Uiso 1 1 calc R . .
H1B H 0.5521 0.7088 0.3157 0.035 Uiso 1 1 calc R . .
H1C H 0.3871 0.7910 0.3100 0.035 Uiso 1 1 calc R . .
N2 N 0.0094(2) 0.77257(18) 0.63126(12) 0.0210(4) Uani 1 1 d . . .
H2A H 0.0659 0.7039 0.6578 0.031 Uiso 1 1 calc R . .
H2B H -0.0996 0.7857 0.6539 0.031 Uiso 1 1 calc R . .
H2C H 0.0757 0.8525 0.6496 0.031 Uiso 1 1 calc R . .
O1 O -0.1758(2) 0.45721(15) 0.29814(12) 0.0266(4) Uani 1 1 d . . .
O2 O -0.2328(2) 0.67188(15) 0.27037(12) 0.0280(4) Uani 1 1 d . . .
O3 O 0.6855(2) 0.81494(15) 0.70723(12) 0.0289(4) Uani 1 1 d . . .
O4 O 0.7235(2) 1.04505(15) 0.72417(12) 0.0290(4) Uani 1 1 d . . .
C1 C -0.1460(2) 0.5605(2) 0.25844(14) 0.0172(4) Uani 1 1 d . . .
C2 C 0.0043(2) 0.55301(19) 0.19211(13) 0.0163(4) Uani 1 1 d . . .
C3 C 0.1316(3) 0.4479(2) 0.18960(14) 0.0184(4) Uani 1 1 d . . .
H3 H 0.1227 0.3793 0.2295 0.022 Uiso 1 1 calc R . .
C4 C 0.2708(3) 0.4424(2) 0.12965(14) 0.0195(4) Uani 1 1 d . . .
H4 H 0.3575 0.3724 0.1310 0.023 Uiso 1 1 calc R . .
C5 C 0.2840(2) 0.5401(2) 0.06695(14) 0.0174(4) Uani 1 1 d . . .
C6 C 0.1544(3) 0.6437(2) 0.06900(15) 0.0212(4) Uani 1 1 d . . .
H6 H 0.1594 0.7099 0.0269 0.025 Uiso 1 1 calc R . .
C7 C 0.0188(3) 0.6513(2) 0.13148(15) 0.0202(4) Uani 1 1 d . . .
H7 H -0.0645 0.7241 0.1328 0.024 Uiso 1 1 calc R . .
C8 C 0.4263(3) 0.5386(2) 0.00024(15) 0.0202(4) Uani 1 1 d . . .
H8 H 0.4120 0.5983 -0.0470 0.024 Uiso 1 1 calc R . .
C9 C 0.6460(3) 0.9392(2) 0.74156(14) 0.0183(4) Uani 1 1 d . . .
C10 C 0.4958(2) 0.9619(2) 0.80827(14) 0.0162(4) Uani 1 1 d . . .
C11 C 0.4772(3) 1.0920(2) 0.86866(15) 0.0206(4) Uani 1 1 d . . .
H11 H 0.5573 1.1661 0.8668 0.025 Uiso 1 1 calc R . .
C12 C 0.3417(3) 1.1135(2) 0.93152(15) 0.0216(4) Uani 1 1 d . . .
H12 H 0.3339 1.2014 0.9735 0.026 Uiso 1 1 calc R . .
C13 C 0.2168(3) 1.0079(2) 0.93406(14) 0.0178(4) Uani 1 1 d . . .
C14 C 0.2350(3) 0.8774(2) 0.87263(14) 0.0194(4) Uani 1 1 d . . .
H14 H 0.1519 0.8044 0.8724 0.023 Uiso 1 1 calc R . .
C15 C 0.3742(3) 0.8546(2) 0.81206(14) 0.0178(4) Uani 1 1 d . . .
H15 H 0.3867 0.7653 0.7730 0.021 Uiso 1 1 calc R . .
C16 C 0.0743(3) 1.0386(2) 1.00075(15) 0.0210(4) Uani 1 1 d . . .
H16 H 0.0893 1.1211 1.0496 0.025 Uiso 1 1 calc R . .
C17 C 0.4740(3) 0.7770(2) 0.45013(17) 0.0275(5) Uani 1 1 d . . .
H17A H 0.5557 0.8591 0.4644 0.033 Uiso 1 1 calc R . .
H17B H 0.5318 0.7038 0.4825 0.033 Uiso 1 1 calc R . .
C18 C 0.2983(3) 0.8165(2) 0.49458(16) 0.0247(5) Uani 1 1 d . . .
H18A H 0.3248 0.8517 0.5670 0.030 Uiso 1 1 calc R . .
H18B H 0.2434 0.8925 0.4642 0.030 Uiso 1 1 calc R . .
C19 C 0.1638(3) 0.6944(2) 0.47800(15) 0.0233(4) Uani 1 1 d . . .
H19A H 0.1399 0.6579 0.4056 0.028 Uiso 1 1 calc R . .
H19B H 0.2181 0.6193 0.5096 0.028 Uiso 1 1 calc R . .
C20 C -0.0138(3) 0.7323(2) 0.51974(16) 0.0258(5) Uani 1 1 d . . .
H20A H -0.0661 0.8105 0.4909 0.031 Uiso 1 1 calc R . .
H20B H -0.0981 0.6520 0.4997 0.031 Uiso 1 1 calc R . .
O1W O 0.5202(2) 0.55257(17) 0.63501(12) 0.0295(4) Uani 1 1 d . . .
H1WA H 0.411(5) 0.559(4) 0.657(3) 0.069(11) Uiso 1 1 d . . .
H1WB H 0.565(5) 0.647(4) 0.663(2) 0.062(10) Uiso 1 1 d . . .
O2W O -0.0679(2) 0.94004(17) 0.33148(13) 0.0310(4) Uani 1 1 d . . .
H2WA H 0.045(5) 0.933(4) 0.308(3) 0.071(11) Uiso 1 1 d . . .
H2WB H -0.121(4) 0.859(3) 0.304(2) 0.043(8) 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 0.0000 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C1 O1 124.47(17) . . ?
O2 C1 C2 116.77(17) . . ?
O1 C1 C2 118.76(17) . . ?
C7 C2 C3 118.19(17) . . ?
C7 C2 C1 120.35(17) . . ?
C3 C2 C1 121.46(17) . . ?
C4 C3 C2 121.28(17) . . ?
C3 C4 C5 120.68(18) . . ?
C6 C5 C4 117.55(17) . . ?
C6 C5 C8 119.05(17) . . ?
C4 C5 C8 123.40(18) . . ?
C7 C6 C5 121.54(18) . . ?
C6 C7 C2 120.72(18) . . ?
C8 C8 C5 126.6(2) 2_665 . ?
O4 C9 O3 124.27(17) . . ?
O4 C9 C10 117.93(17) . . ?
O3 C9 C10 117.80(17) . . ?
C11 C10 C15 118.41(17) . . ?
C11 C10 C9 120.01(17) . . ?
C15 C10 C9 121.57(16) . . ?
C12 C11 C10 120.56(18) . . ?
C11 C12 C13 121.49(17) . . ?
C12 C13 C14 117.79(17) . . ?
C12 C13 C16 118.72(17) . . ?
C14 C13 C16 123.48(18) . . ?
C15 C14 C13 120.70(18) . . ?
C14 C15 C10 121.00(17) . . ?
C16 C16 C13 126.7(2) 2_577 . ?
N1 C17 C18 112.09(18) . . ?
C19 C18 C17 113.02(17) . . ?
C20 C19 C18 113.85(17) . . ?
N2 C20 C19 111.83(17) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C17 1.485(3) . ?
N2 C20 1.487(3) . ?
O1 C1 1.254(2) . ?
O2 C1 1.254(2) . ?
O3 C9 1.258(2) . ?
O4 C9 1.250(2) . ?
C1 C2 1.506(2) . ?
C2 C7 1.383(3) . ?
C2 C3 1.393(3) . ?
C3 C4 1.382(3) . ?
C4 C5 1.398(3) . ?
C5 C6 1.394(3) . ?
C5 C8 1.466(2) . ?
C6 C7 1.382(3) . ?
C8 C8 1.330(4) 2_665 ?
C9 C10 1.506(2) . ?
C10 C11 1.389(3) . ?
C10 C15 1.392(3) . ?
C11 C12 1.383(3) . ?
C12 C13 1.392(3) . ?
C13 C14 1.398(3) . ?
C13 C16 1.465(3) . ?
C14 C15 1.386(3) . ?
C16 C16 1.333(4) 2_577 ?
C17 C18 1.520(3) . ?
C18 C19 1.520(3) . ?
C19 C20 1.515(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1W 0.90 2.20 2.794(2) 122.6 2_666
N1 H1B O2 0.90 1.79 2.691(2) 178.3 1_655
N1 H1C O4 0.90 1.90 2.789(2) 167.3 2_676
N2 H2A O1 0.90 1.93 2.826(2) 173.8 2_566
N2 H2B O3 0.90 1.83 2.728(2) 176.8 1_455
N2 H2C O2W 0.90 1.98 2.767(2) 144.5 2_576
O1W H1WA O1 0.90(4) 1.93(4) 2.820(2) 172(3) 2_566
O1W H1WB O3 0.97(4) 1.83(4) 2.789(2) 170(3) .
O2W H2WA O4 0.93(4) 1.85(4) 2.764(2) 168(3) 2_676
O2W H2WB O2 0.88(3) 1.95(3) 2.819(2) 168(3) .
