#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/58/2235811.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_2235811
loop_
_publ_author_name
'Troshin, Konstantin'
'Mayer, Peter'
'Mayr, Herbert'
_publ_section_title
;
 (R,E)-3-(4-Chlorophenyl)-1-phenylallyl 4-nitrobenzoate
;
_journal_coeditor_code           GG2092
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2549
_journal_paper_doi               10.1107/S1600536812032813
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C22 H16 Cl N O4'
_chemical_formula_moiety         'C22 H16 Cl N O4'
_chemical_formula_sum            'C22 H16 Cl N O4'
_chemical_formula_weight         393.819
_chemical_name_systematic
;
(R,E)-3-(4-Chlorophenyl)-1-phenylallyl 4-nitrobenzoate
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.38170(10)
_cell_length_b                   9.9238(2)
_cell_length_c                   22.8090(4)
_cell_measurement_reflns_used    6811
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      3.134
_cell_volume                     1897.21(6)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction
'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'CCD; rotation images; thick slices'
_diffrn_radiation_monochromator  'MONTEL, graded multilayered X-ray optics'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            12403
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         3.18
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.38
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.191
_refine_ls_abs_structure_details 'Flack (1983), 1854 Friedel pairs'
_refine_ls_abs_structure_Flack   0.01(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4331
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.039P)²+0.3359P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0829
_reflns_number_gt                3847
_reflns_number_total             4331
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg2092.cif
_cod_data_source_block           I
_cod_database_code               2235811
_cod_database_fobs_code          2235811
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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_symmetry_multiplicity
Cl Cl1 1.05905(6) -0.23586(5) 0.67154(2) 0.04970(13) Uani d . 1 1
O O1 1.0670(2) -0.12603(15) 0.07501(6) 0.0654(4) Uani d . 1 1
O O2 1.1347(2) 0.07816(17) 0.05567(6) 0.0674(4) Uani d . 1 1
O O3 0.69865(12) 0.07772(10) 0.32577(5) 0.0306(2) Uani d . 1 1
O O4 0.72705(18) 0.29656(12) 0.30153(5) 0.0476(3) Uani d . 1 1
N N1 1.0677(2) -0.00643(17) 0.08602(6) 0.0456(4) Uani d . 1 1
C C1 0.9715(2) -0.14740(16) 0.61393(7) 0.0348(4) Uani d . 1 1
C C2 0.9926(2) -0.01089(18) 0.61008(8) 0.0433(4) Uani d . 1 1
H H2 1.0551 0.0358 0.6383 0.052 Uiso calc R 1 1
C C3 0.9209(2) 0.05778(18) 0.56419(7) 0.0423(4) Uani d . 1 1
H H3 0.9343 0.1526 0.5614 0.051 Uiso calc R 1 1
C C4 0.82999(18) -0.00806(16) 0.52214(7) 0.0308(3) Uani d . 1 1
C C5 0.8104(2) -0.14624(17) 0.52765(8) 0.0403(4) Uani d . 1 1
H H5 0.7480 -0.1936 0.4996 0.048 Uiso calc R 1 1
C C6 0.8806(2) -0.21628(17) 0.57359(8) 0.0441(4) Uani d . 1 1
H H6 0.8662 -0.3109 0.5771 0.053 Uiso calc R 1 1
C C7 0.75987(18) 0.07074(16) 0.47422(7) 0.0317(3) Uani d . 1 1
H H7 0.7667 0.1660 0.4776 0.038 Uiso calc R 1 1
C C8 0.68791(18) 0.02343(16) 0.42667(7) 0.0304(3) Uani d . 1 1
H H8 0.6799 -0.0714 0.4218 0.036 Uiso calc R 1 1
C C9 0.61891(17) 0.11246(16) 0.38042(6) 0.0289(3) Uani d . 1 1
H H9 0.6421 0.2087 0.3903 0.035 Uiso calc R 1 1
C C10 0.43980(17) 0.09433(14) 0.37273(6) 0.0284(3) Uani d . 1 1
C C11 0.36984(18) 0.08652(17) 0.31807(7) 0.0357(4) Uani d . 1 1
H H11 0.4345 0.0910 0.2839 0.043 Uiso calc R 1 1
C C12 0.2058(2) 0.07210(19) 0.31259(8) 0.0441(4) Uani d . 1 1
H H12 0.1587 0.0677 0.2748 0.053 Uiso calc R 1 1
C C13 0.11123(19) 0.06417(19) 0.36165(9) 0.0438(4) Uani d . 1 1
H H13 -0.0009 0.0534 0.3578 0.053 Uiso calc R 1 1
C C14 0.1797(2) 0.07192(18) 0.41646(8) 0.0409(4) Uani d . 1 1
H H14 0.1145 0.0669 0.4505 0.049 Uiso calc R 1 1
C C15 0.34379(19) 0.08698(16) 0.42224(7) 0.0335(3) Uani d . 1 1
H H15 0.3904 0.0923 0.4601 0.040 Uiso calc R 1 1
C C16 0.74556(18) 0.17917(16) 0.29088(7) 0.0308(3) Uani d . 1 1
C C17 0.82662(18) 0.12685(16) 0.23721(6) 0.0294(3) Uani d . 1 1
C C18 0.8264(2) -0.00856(17) 0.22281(7) 0.0377(4) Uani d . 1 1
H H18 0.7725 -0.0714 0.2472 0.045 Uiso calc R 1 1
C C19 0.9049(2) -0.05269(17) 0.17272(8) 0.0417(4) Uani d . 1 1
H H19 0.9046 -0.1453 0.1621 0.050 Uiso calc R 1 1
C C20 0.98271(19) 0.04050(17) 0.13903(7) 0.0354(4) Uani d . 1 1
C C21 0.9847(2) 0.17555(18) 0.15197(8) 0.0440(4) Uani d . 1 1
H H21 1.0391 0.2378 0.1275 0.053 Uiso calc R 1 1
C C22 0.9051(2) 0.21839(17) 0.20181(7) 0.0412(4) Uani d . 1 1
H H22 0.9045 0.3114 0.2117 0.049 Uiso calc R 1 1
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'
Cl Cl 0.1484 0.1585 '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
C16 O3 C9 117.68(12)
O1 N1 O2 123.77(16)
O1 N1 C20 118.37(15)
O2 N1 C20 117.86(16)
C2 C1 C6 121.35(16)
C2 C1 Cl1 119.49(13)
C6 C1 Cl1 119.15(13)
C1 C2 C3 118.60(16)
C1 C2 H2 120.7
C3 C2 H2 120.7
C2 C3 C4 121.90(16)
C2 C3 H3 119.1
C4 C3 H3 119.1
C5 C4 C3 117.89(15)
C5 C4 C7 123.18(15)
C3 C4 C7 118.93(14)
C4 C5 C6 120.87(15)
C4 C5 H5 119.6
C6 C5 H5 119.6
C1 C6 C5 119.38(16)
C1 C6 H6 120.3
C5 C6 H6 120.3
C8 C7 C4 127.06(15)
C8 C7 H7 116.5
C4 C7 H7 116.5
C7 C8 C9 122.99(15)
C7 C8 H8 118.5
C9 C8 H8 118.5
O3 C9 C8 106.69(12)
O3 C9 C10 109.04(12)
C8 C9 C10 113.18(13)
O3 C9 H9 109.3
C8 C9 H9 109.3
C10 C9 H9 109.3
C11 C10 C15 119.05(13)
C11 C10 C9 121.99(13)
C15 C10 C9 118.96(13)
C10 C11 C12 120.54(15)
C10 C11 H11 119.7
C12 C11 H11 119.7
C13 C12 C11 120.26(16)
C13 C12 H12 119.9
C11 C12 H12 119.9
C12 C13 C14 119.71(15)
C12 C13 H13 120.1
C14 C13 H13 120.1
C13 C14 C15 120.30(16)
C13 C14 H14 119.8
C15 C14 H14 119.8
C10 C15 C14 120.13(15)
C10 C15 H15 119.9
C14 C15 H15 119.9
O4 C16 O3 124.77(14)
O4 C16 C17 124.22(14)
O3 C16 C17 111.01(13)
C22 C17 C18 120.02(15)
C22 C17 C16 117.84(14)
C18 C17 C16 122.14(14)
C17 C18 C19 120.07(15)
C17 C18 H18 120.0
C19 C18 H18 120.0
C20 C19 C18 118.33(15)
C20 C19 H19 120.8
C18 C19 H19 120.8
C19 C20 C21 123.05(15)
C19 C20 N1 118.43(15)
C21 C20 N1 118.53(15)
C20 C21 C22 118.06(16)
C20 C21 H21 121.0
C22 C21 H21 121.0
C17 C22 C21 120.47(16)
C17 C22 H22 119.8
C21 C22 H22 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.7424(16)
O1 N1 1.213(2)
O2 N1 1.224(2)
O3 C16 1.3422(18)
O3 C9 1.4557(17)
O4 C16 1.200(2)
N1 C20 1.479(2)
C1 C2 1.369(2)
C1 C6 1.376(2)
C2 C3 1.386(2)
C2 H2 0.9500
C3 C4 1.388(2)
C3 H3 0.9500
C4 C5 1.387(2)
C4 C7 1.467(2)
C5 C6 1.389(2)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.327(2)
C7 H7 0.9500
C8 C9 1.493(2)
C8 H8 0.9500
C9 C10 1.522(2)
C9 H9 1.0000
C10 C11 1.380(2)
C10 C15 1.389(2)
C11 C12 1.388(2)
C11 H11 0.9500
C12 C13 1.373(3)
C12 H12 0.9500
C13 C14 1.378(3)
C13 H13 0.9500
C14 C15 1.389(2)
C14 H14 0.9500
C15 H15 0.9500
C16 C17 1.493(2)
C17 C22 1.382(2)
C17 C18 1.383(2)
C18 C19 1.389(2)
C18 H18 0.9500
C19 C20 1.368(2)
C19 H19 0.9500
C20 C21 1.372(2)
C21 C22 1.385(2)
C21 H21 0.9500
C22 H22 0.9500
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
_geom_hbond_publ_flag
C2 H2 O4 3_556 0.95 2.59 3.529(2) 168 yes
C12 H12 Cg 1_455 0.95 2.92 3.8072(19) 157 yes
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 -0.3(3)
Cl1 C1 C2 C3 -179.48(14)
C1 C2 C3 C4 -0.5(3)
C2 C3 C4 C5 0.9(3)
C2 C3 C4 C7 -178.96(17)
C3 C4 C5 C6 -0.5(3)
C7 C4 C5 C6 179.38(16)
C2 C1 C6 C5 0.7(3)
Cl1 C1 C6 C5 179.90(14)
C4 C5 C6 C1 -0.3(3)
C5 C4 C7 C8 -9.2(3)
C3 C4 C7 C8 170.68(15)
C4 C7 C8 C9 179.48(14)
C16 O3 C9 C8 -136.58(13)
C16 O3 C9 C10 100.86(15)
C7 C8 C9 O3 121.40(15)
C7 C8 C9 C10 -118.67(16)
O3 C9 C10 C11 -17.5(2)
C8 C9 C10 C11 -136.06(15)
O3 C9 C10 C15 163.25(13)
C8 C9 C10 C15 44.68(19)
C15 C10 C11 C12 0.3(3)
C9 C10 C11 C12 -178.98(16)
C10 C11 C12 C13 -0.6(3)
C11 C12 C13 C14 0.6(3)
C12 C13 C14 C15 -0.3(3)
C11 C10 C15 C14 0.0(2)
C9 C10 C15 C14 179.30(15)
C13 C14 C15 C10 0.0(3)
C9 O3 C16 O4 0.3(2)
C9 O3 C16 C17 179.34(11)
O4 C16 C17 C22 9.7(2)
O3 C16 C17 C22 -169.42(14)
O4 C16 C17 C18 -171.07(18)
O3 C16 C17 C18 9.8(2)
C22 C17 C18 C19 -0.1(3)
C16 C17 C18 C19 -179.32(15)
C17 C18 C19 C20 0.7(3)
C18 C19 C20 C21 -1.0(3)
C18 C19 C20 N1 179.41(15)
O1 N1 C20 C19 -1.1(3)
O2 N1 C20 C19 178.82(17)
O1 N1 C20 C21 179.29(18)
O2 N1 C20 C21 -0.8(3)
C19 C20 C21 C22 0.6(3)
N1 C20 C21 C22 -179.82(16)
C18 C17 C22 C21 -0.3(3)
C16 C17 C22 C21 178.93(16)
C20 C21 C22 C17 0.1(3)
