#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/71/2237153.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_2237153
loop_
_publ_author_name
'Kedjadja, Allaoua'
'Merdes, Rachid'
'Bouacida, Sofiane'
'Roisnel, Thierry'
'Belfaitah, Ali'
_publ_section_title
;
 (2E,2'E)-1,1'-Bis(6-chloro-2-methyl-4-phenylquinolin-3-yl)-3,3'-(1,4-phenylene)diprop-2-en-1-one
 ethyl acetate disolvate
;
_journal_coeditor_code           HB7004
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o37
_journal_page_last               o38
_journal_paper_doi               10.1107/S1600536812049422
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C44 H30 Cl2 N2 O2, 2C4 H8 O2'
_chemical_formula_moiety         'C44 H30 Cl2 N2 O2, 2(C4 H8 O2)'
_chemical_formula_sum            'C52 H46 Cl2 N2 O6'
_chemical_formula_weight         865.81
_chemical_name_systematic
;
(2E,2'E)-1,1'-Bis(6-chloro-2-methyl-4-phenylquinolin-3-
yl)-3,3'-(1,4-phenylene)diprop-2-en-1-one ethyl acetate disolvate
;
_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
_cell_angle_alpha                102.3500(10)
_cell_angle_beta                 97.1080(10)
_cell_angle_gamma                95.290(2)
_cell_formula_units_Z            1
_cell_length_a                   9.9851(3)
_cell_length_b                   10.0086(2)
_cell_length_c                   11.3676(3)
_cell_measurement_reflns_used    8289
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.46
_cell_volume                     1092.94(5)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2002 (Burla et al., 2005)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18119
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.76
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS;  Sheldrick, 2002)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             454
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.021
_refine_diff_density_min         -0.424
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4866
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0483
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0694P)²+0.8188P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1312
_refine_ls_wR_factor_ref         0.1402
_reflns_number_gt                4035
_reflns_number_total             4866
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7004.cif
_cod_data_source_block           I
_cod_database_code               2237153
_cod_database_fobs_code          2237153
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O O53 0.31158(16) 0.42524(16) 0.11802(16) 0.0417(4) Uani d . 1 1
Cl Cl1 0.31876(5) 0.75570(5) 0.69990(4) 0.02960(15) Uani d . 1 1
C C1 0.23208(18) 0.65060(19) 0.56441(16) 0.0234(4) Uani d . 1 1
C C2 0.15254(19) 0.70928(19) 0.48229(18) 0.0265(4) Uani d . 1 1
H H2 0.1473 0.8057 0.4995 0.032 Uiso calc R 1 1
C C3 0.08296(19) 0.6252(2) 0.37739(18) 0.0265(4) Uani d . 1 1
H H3 0.0294 0.6642 0.3215 0.032 Uiso calc R 1 1
C C4 0.08921(18) 0.48125(18) 0.35046(16) 0.0220(4) Uani d . 1 1
C C5 0.17208(17) 0.42485(18) 0.43299(16) 0.0209(4) Uani d . 1 1
C C6 0.24378(18) 0.51286(18) 0.54149(16) 0.0226(4) Uani d . 1 1
H H6 0.2995 0.4763 0.5978 0.027 Uiso calc R 1 1
N N7 0.01376(16) 0.40156(16) 0.24584(14) 0.0248(3) Uani d . 1 1
C C8 0.01928(18) 0.26750(19) 0.22137(16) 0.0232(4) Uani d . 1 1
C C9 -0.0649(2) 0.1817(2) 0.10685(18) 0.0309(4) Uani d . 1 1
H H9A -0.1169 0.2411 0.0654 0.046 Uiso calc R 1 1
H H9B -0.1277 0.112 0.1274 0.046 Uiso calc R 1 1
H H9C -0.0051 0.1361 0.0531 0.046 Uiso calc R 1 1
C C10 0.10213(17) 0.20250(18) 0.29886(16) 0.0210(4) Uani d . 1 1
C C11 0.17907(17) 0.28022(18) 0.40423(16) 0.0206(4) Uani d . 1 1
C C12 0.26671(18) 0.21649(18) 0.48762(16) 0.0214(4) Uani d . 1 1
C C13 0.20937(19) 0.14663(19) 0.56647(18) 0.0262(4) Uani d . 1 1
H H13 0.1138 0.1385 0.5664 0.031 Uiso calc R 1 1
C C14 0.2911(2) 0.0889(2) 0.64504(18) 0.0300(4) Uani d . 1 1
H H14 0.2515 0.0424 0.6993 0.036 Uiso calc R 1 1
C C15 0.4301(2) 0.0989(2) 0.64447(18) 0.0305(4) Uani d . 1 1
H H15 0.4858 0.0584 0.6976 0.037 Uiso calc R 1 1
C C16 0.4880(2) 0.1681(2) 0.56644(19) 0.0303(4) Uani d . 1 1
H H16 0.5834 0.1745 0.5658 0.036 Uiso calc R 1 1
C C17 0.40700(19) 0.2279(2) 0.48915(17) 0.0265(4) Uani d . 1 1
H H17 0.4474 0.2769 0.437 0.032 Uiso calc R 1 1
C C18 0.10551(18) 0.04827(18) 0.26507(16) 0.0228(4) Uani d . 1 1
O O19 0.02241(15) -0.02933(15) 0.29611(15) 0.0380(4) Uani d . 1 1
C C20 0.21001(18) -0.00520(18) 0.19329(16) 0.0218(4) Uani d . 1 1
H H20 0.2189 -0.1008 0.1793 0.026 Uiso calc R 1 1
C C21 0.29293(17) 0.07597(18) 0.14703(15) 0.0202(3) Uani d . 1 1
H H21 0.2831 0.1714 0.1651 0.024 Uiso calc R 1 1
C C22 0.39718(17) 0.03406(17) 0.07162(15) 0.0191(3) Uani d . 1 1
C C23 0.47009(18) 0.13423(18) 0.02708(16) 0.0216(4) Uani d . 1 1
H H23 0.4496 0.2266 0.0455 0.026 Uiso calc R 1 1
C C24 0.57142(18) 0.10142(18) -0.04320(16) 0.0218(4) Uani d . 1 1
H H24 0.6197 0.1711 -0.0722 0.026 Uiso calc R 1 1
C C51 0.5390(2) 0.5546(3) 0.1748(2) 0.0432(5) Uani d . 1 1
H H51A 0.5797 0.4728 0.139 0.065 Uiso calc R 1 1
H H51B 0.6037 0.6128 0.2421 0.065 Uiso calc R 1 1
H H51C 0.5165 0.6066 0.1127 0.065 Uiso calc R 1 1
C C52 0.4113(2) 0.5106(2) 0.2220(2) 0.0398(5) Uani d . 1 1
H H52A 0.4331 0.4563 0.2836 0.048 Uiso calc R 1 1
H H52B 0.3716 0.5928 0.2611 0.048 Uiso calc R 1 1
C C54 0.2331(2) 0.4949(3) 0.0581(2) 0.0412(5) Uani d . 1 1
C C55 0.1442(3) 0.3999(3) -0.0465(2) 0.0465(6) Uani d . 1 1
H H55A 0.0557 0.376 -0.0225 0.07 Uiso calc R 1 1
H H55B 0.1867 0.3159 -0.0712 0.07 Uiso calc R 1 1
H H55C 0.1314 0.4451 -0.1148 0.07 Uiso calc R 1 1
O O56 0.23575(18) 0.61974(16) 0.08844(18) 0.0503(5) Uani d . 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 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C54 O53 C52 . . 115.38(17)
C6 C1 C2 . . 122.05(17)
C6 C1 Cl1 . . 118.43(14)
C2 C1 Cl1 . . 119.52(14)
C3 C2 C1 . . 118.92(17)
C3 C2 H2 . . 120.5
C1 C2 H2 . . 120.5
C2 C3 C4 . . 121.30(17)
C2 C3 H3 . . 119.4
C4 C3 H3 . . 119.4
N7 C4 C5 . . 122.46(16)
N7 C4 C3 . . 118.70(16)
C5 C4 C3 . . 118.84(16)
C4 C5 C6 . . 119.40(16)
C4 C5 C11 . . 118.38(16)
C6 C5 C11 . . 122.22(16)
C1 C6 C5 . . 119.46(17)
C1 C6 H6 . . 120.3
C5 C6 H6 . . 120.3
C8 N7 C4 . . 118.54(16)
N7 C8 C10 . . 122.57(16)
N7 C8 C9 . . 117.80(16)
C10 C8 C9 . . 119.64(16)
C8 C9 H9A . . 109.5
C8 C9 H9B . . 109.5
H9A C9 H9B . . 109.5
C8 C9 H9C . . 109.5
H9A C9 H9C . . 109.5
H9B C9 H9C . . 109.5
C11 C10 C8 . . 120.02(16)
C11 C10 C18 . . 119.87(16)
C8 C10 C18 . . 120.11(16)
C10 C11 C5 . . 118.01(16)
C10 C11 C12 . . 121.72(16)
C5 C11 C12 . . 120.27(16)
C17 C12 C13 . . 119.09(17)
C17 C12 C11 . . 120.53(16)
C13 C12 C11 . . 120.37(16)
C14 C13 C12 . . 120.34(17)
C14 C13 H13 . . 119.8
C12 C13 H13 . . 119.8
C15 C14 C13 . . 120.11(18)
C15 C14 H14 . . 119.9
C13 C14 H14 . . 119.9
C14 C15 C16 . . 119.97(18)
C14 C15 H15 . . 120
C16 C15 H15 . . 120
C15 C16 C17 . . 120.13(18)
C15 C16 H16 . . 119.9
C17 C16 H16 . . 119.9
C16 C17 C12 . . 120.35(17)
C16 C17 H17 . . 119.8
C12 C17 H17 . . 119.8
O19 C18 C20 . . 121.15(16)
O19 C18 C10 . . 120.30(15)
C20 C18 C10 . . 118.54(15)
C21 C20 C18 . . 122.36(16)
C21 C20 H20 . . 118.8
C18 C20 H20 . . 118.8
C20 C21 C22 . . 127.20(16)
C20 C21 H21 . . 116.4
C22 C21 H21 . . 116.4
C24 C22 C23 2_655 . 118.45(15)
C24 C22 C21 2_655 . 122.88(16)
C23 C22 C21 . . 118.67(15)
C24 C23 C22 . . 121.39(16)
C24 C23 H23 . . 119.3
C22 C23 H23 . . 119.3
C23 C24 C22 . 2_655 120.16(16)
C23 C24 H24 . . 119.9
C22 C24 H24 2_655 . 119.9
C52 C51 H51A . . 109.5
C52 C51 H51B . . 109.5
H51A C51 H51B . . 109.5
C52 C51 H51C . . 109.5
H51A C51 H51C . . 109.5
H51B C51 H51C . . 109.5
O53 C52 C51 . . 109.09(18)
O53 C52 H52A . . 109.9
C51 C52 H52A . . 109.9
O53 C52 H52B . . 109.9
C51 C52 H52B . . 109.9
H52A C52 H52B . . 108.3
O56 C54 O53 . . 122.8(2)
O56 C54 C55 . . 126.9(2)
O53 C54 C55 . . 110.3(2)
C54 C55 H55A . . 109.5
C54 C55 H55B . . 109.5
H55A C55 H55B . . 109.5
C54 C55 H55C . . 109.5
H55A C55 H55C . . 109.5
H55B C55 H55C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O53 C54 . 1.318(3)
O53 C52 . 1.496(3)
Cl1 C1 . 1.7427(18)
C1 C6 . 1.366(3)
C1 C2 . 1.409(3)
C2 C3 . 1.368(3)
C2 H2 . 0.95
C3 C4 . 1.417(3)
C3 H3 . 0.95
C4 N7 . 1.371(2)
C4 C5 . 1.416(3)
C5 C6 . 1.418(2)
C5 C11 . 1.424(2)
C6 H6 . 0.95
N7 C8 . 1.319(2)
C8 C10 . 1.431(3)
C8 C9 . 1.502(3)
C9 H9A . 0.98
C9 H9B . 0.98
C9 H9C . 0.98
C10 C11 . 1.376(2)
C10 C18 . 1.513(2)
C11 C12 . 1.493(2)
C12 C17 . 1.393(3)
C12 C13 . 1.393(3)
C13 C14 . 1.388(3)
C13 H13 . 0.95
C14 C15 . 1.383(3)
C14 H14 . 0.95
C15 C16 . 1.384(3)
C15 H15 . 0.95
C16 C17 . 1.387(3)
C16 H16 . 0.95
C17 H17 . 0.95
C18 O19 . 1.219(2)
C18 C20 . 1.472(2)
C20 C21 . 1.337(2)
C20 H20 . 0.95
C21 C22 . 1.464(2)
C21 H21 . 0.95
C22 C24 2_655 1.399(2)
C22 C23 . 1.402(2)
C23 C24 . 1.385(2)
C23 H23 . 0.95
C24 C22 2_655 1.399(2)
C24 H24 . 0.95
C51 C52 . 1.507(3)
C51 H51A . 0.98
C51 H51B . 0.98
C51 H51C . 0.98
C52 H52A . 0.99
C52 H52B . 0.99
C54 O56 . 1.219(3)
C54 C55 . 1.485(3)
C55 H55A . 0.98
C55 H55B . 0.98
C55 H55C . 0.98
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
C13 H13 O19 2_556 0.95 2.54 3.218(2) 128 yes
C23 H23 O53 . 0.95 2.57 3.468(2) 157 yes
C24 H24 O56 2_665 0.95 2.48 3.410(3) 165 yes
C51 H51B Cg1 2_666 0.98 2.76 3.627(3) 147 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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C6 C1 C2 C3 . . 1.2(3)
Cl1 C1 C2 C3 . . -178.76(14)
C1 C2 C3 C4 . . 0.2(3)
C2 C3 C4 N7 . . 177.88(17)
C2 C3 C4 C5 . . -1.6(3)
N7 C4 C5 C6 . . -177.88(16)
C3 C4 C5 C6 . . 1.5(2)
N7 C4 C5 C11 . . 1.4(3)
C3 C4 C5 C11 . . -179.16(16)
C2 C1 C6 C5 . . -1.2(3)
Cl1 C1 C6 C5 . . 178.76(13)
C4 C5 C6 C1 . . -0.2(3)
C11 C5 C6 C1 . . -179.47(16)
C5 C4 N7 C8 . . -0.2(3)
C3 C4 N7 C8 . . -179.66(16)
C4 N7 C8 C10 . . -0.8(3)
C4 N7 C8 C9 . . 179.53(16)
N7 C8 C10 C11 . . 0.7(3)
C9 C8 C10 C11 . . -179.70(16)
N7 C8 C10 C18 . . -179.25(16)
C9 C8 C10 C18 . . 0.4(2)
C8 C10 C11 C5 . . 0.6(2)
C18 C10 C11 C5 . . -179.55(14)
C8 C10 C11 C12 . . 179.94(15)
C18 C10 C11 C12 . . -0.2(2)
C4 C5 C11 C10 . . -1.5(2)
C6 C5 C11 C10 . . 177.76(15)
C4 C5 C11 C12 . . 179.09(15)
C6 C5 C11 C12 . . -1.6(2)
C10 C11 C12 C17 . . 103.4(2)
C5 C11 C12 C17 . . -77.3(2)
C10 C11 C12 C13 . . -77.7(2)
C5 C11 C12 C13 . . 101.7(2)
C17 C12 C13 C14 . . -0.2(3)
C11 C12 C13 C14 . . -179.20(17)
C12 C13 C14 C15 . . -0.8(3)
C13 C14 C15 C16 . . 0.8(3)
C14 C15 C16 C17 . . 0.3(3)
C15 C16 C17 C12 . . -1.3(3)
C13 C12 C17 C16 . . 1.3(3)
C11 C12 C17 C16 . . -179.74(17)
C11 C10 C18 O19 . . 92.4(2)
C8 C10 C18 O19 . . -87.7(2)
C11 C10 C18 C20 . . -88.2(2)
C8 C10 C18 C20 . . 91.7(2)
O19 C18 C20 C21 . . 172.69(18)
C10 C18 C20 C21 . . -6.7(3)
C18 C20 C21 C22 . . -178.00(16)
C20 C21 C22 C24 . 2_655 -3.7(3)
C20 C21 C22 C23 . . 177.15(17)
C24 C22 C23 C24 2_655 . -0.2(3)
C21 C22 C23 C24 . . 179.00(16)
C22 C23 C24 C22 . 2_655 0.2(3)
C54 O53 C52 C51 . . -86.6(2)
C52 O53 C54 O56 . . -3.7(3)
C52 O53 C54 C55 . . 176.92(18)
