#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/13/2221316.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_2221316
loop_
_publ_author_name
'Liu, Deyun'
_publ_section_title
;
 2,6-Bis(2-chlorobenzylidene)cyclohexanone
;
_journal_coeditor_code           CV2518
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o694
_journal_paper_doi               10.1107/S1600536809007648
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H16 Cl2 O'
_chemical_formula_moiety         'C20 H16 Cl2 O'
_chemical_formula_sum            'C20 H16 Cl2 O'
_chemical_formula_weight         343.23
_chemical_name_systematic        ?
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.4004(15)
_cell_length_b                   8.1553(10)
_cell_length_c                   28.593(3)
_cell_measurement_reflns_used    2653
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      43.785
_cell_measurement_theta_min      2.829
_cell_volume                     3357.9(6)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX 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  0.0641
_diffrn_reflns_av_sigmaI/netI    0.0519
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            13876
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    0.388
_exptl_absorpt_correction_T_max  0.9370
_exptl_absorpt_correction_T_min  0.8540
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.318
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2962
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0353P)²+3.2692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.1239
_reflns_number_gt                1762
_reflns_number_total             2962
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cv2518.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        3358.0(6)
_cod_database_code               2221316
_cod_database_fobs_code          2221316
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 1.01278(6) 1.01596(12) 0.34622(3) 0.0568(3) Uani d . 1 . .
Cl Cl2 0.72695(8) 0.83897(15) 0.07162(3) 0.0783(4) Uani d . 1 . .
O O1 0.86474(15) 0.7337(3) 0.22424(7) 0.0515(7) Uani d . 1 . .
C C1 0.7861(2) 0.7354(4) 0.24087(10) 0.0342(8) Uani d . 1 . .
C C2 0.7724(2) 0.7802(4) 0.29170(10) 0.0347(8) Uani d . 1 . .
C C3 0.6741(2) 0.8022(5) 0.30951(11) 0.0472(9) Uani d . 1 . .
H H3A 0.6726 0.8954 0.3306 0.057 Uiso calc R 1 . .
H H3B 0.6567 0.7058 0.3273 0.057 Uiso calc R 1 . .
C C4 0.6032(2) 0.8289(5) 0.27104(11) 0.0455(9) Uani d . 1 . .
H H4A 0.6145 0.9334 0.2559 0.055 Uiso calc R 1 . .
H H4B 0.5413 0.8313 0.2844 0.055 Uiso calc R 1 . .
C C5 0.6099(2) 0.6916(4) 0.23542(11) 0.0399(8) Uani d . 1 . .
H H5A 0.6006 0.5870 0.2509 0.048 Uiso calc R 1 . .
H H5B 0.5615 0.7046 0.2122 0.048 Uiso calc R 1 . .
C C6 0.7032(2) 0.6928(4) 0.21178(10) 0.0335(7) Uani d . 1 . .
C C7 0.8490(2) 0.8002(4) 0.31767(10) 0.0412(8) Uani d . 1 . .
H H7 0.9051 0.7861 0.3020 0.049 Uiso calc R 1 . .
C C8 0.8563(2) 0.8412(5) 0.36743(11) 0.0458(9) Uani d . 1 . .
C C9 0.9282(2) 0.9410(5) 0.38404(11) 0.0485(9) Uani d . 1 . .
C C10 0.9346(3) 0.9856(6) 0.43068(13) 0.0654(12) Uani d . 1 . .
H H10 0.9817 1.0555 0.4406 0.078 Uiso calc R 1 . .
C C11 0.8710(3) 0.9260(7) 0.46211(14) 0.0806(15) Uani d . 1 . .
H H11 0.8753 0.9550 0.4935 0.097 Uiso calc R 1 . .
C C12 0.8011(3) 0.8238(7) 0.44739(14) 0.0836(15) Uani d . 1 . .
H H12 0.7585 0.7832 0.4689 0.100 Uiso calc R 1 . .
C C13 0.7935(3) 0.7809(6) 0.40090(12) 0.0626(12) Uani d . 1 . .
H H13 0.7461 0.7108 0.3915 0.075 Uiso calc R 1 . .
C C14 0.7172(2) 0.6681(4) 0.16580(11) 0.0399(8) Uani d . 1 . .
H H14 0.7776 0.6812 0.1549 0.048 Uiso calc R 1 . .
C C15 0.6467(2) 0.6227(4) 0.13110(10) 0.0382(8) Uani d . 1 . .
C C16 0.6448(2) 0.6917(4) 0.08648(11) 0.0444(9) Uani d . 1 . .
C C17 0.5785(3) 0.6500(5) 0.05364(12) 0.0561(10) Uani d . 1 . .
H H17 0.5785 0.7002 0.0244 0.067 Uiso calc R 1 . .
C C18 0.5126(3) 0.5339(5) 0.06440(13) 0.0610(11) Uani d . 1 . .
H H18 0.4672 0.5062 0.0426 0.073 Uiso calc R 1 . .
C C19 0.5141(3) 0.4588(5) 0.10758(13) 0.0588(11) Uani d . 1 . .
H H19 0.4707 0.3781 0.1146 0.071 Uiso calc R 1 . .
C C20 0.5795(2) 0.5029(4) 0.14024(11) 0.0461(9) Uani d . 1 . .
H H20 0.5791 0.4515 0.1693 0.055 Uiso calc R 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 Cl1 O1 . 3_755 165.55(13) ?
O1 C1 C6 . . 121.2(3) ?
O1 C1 C2 . . 119.7(3) ?
C6 C1 C2 . . 119.1(3) ?
C7 C2 C1 . . 117.0(3) ?
C7 C2 C3 . . 124.7(3) ?
C1 C2 C3 . . 118.3(3) ?
C2 C3 C4 . . 113.7(3) ?
C2 C3 H3A . . 108.8 ?
C4 C3 H3A . . 108.8 ?
C2 C3 H3B . . 108.8 ?
C4 C3 H3B . . 108.8 ?
H3A C3 H3B . . 107.7 ?
C3 C4 C5 . . 109.8(3) ?
C3 C4 H4A . . 109.7 ?
C5 C4 H4A . . 109.7 ?
C3 C4 H4B . . 109.7 ?
C5 C4 H4B . . 109.7 ?
H4A C4 H4B . . 108.2 ?
C6 C5 C4 . . 110.7(3) ?
C6 C5 H5A . . 109.5 ?
C4 C5 H5A . . 109.5 ?
C6 C5 H5B . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 108.1 ?
C14 C6 C1 . . 117.4(3) ?
C14 C6 C5 . . 124.9(3) ?
C1 C6 C5 . . 117.7(3) ?
C2 C7 C8 . . 128.7(3) ?
C2 C7 H7 . . 115.7 ?
C8 C7 H7 . . 115.7 ?
C9 C8 C13 . . 116.6(3) ?
C9 C8 C7 . . 121.0(3) ?
C13 C8 C7 . . 122.4(3) ?
C10 C9 C8 . . 121.9(4) ?
C10 C9 Cl1 . . 117.4(3) ?
C8 C9 Cl1 . . 120.8(3) ?
C11 C10 C9 . . 119.6(4) ?
C11 C10 H10 . . 120.2 ?
C9 C10 H10 . . 120.2 ?
C10 C11 C12 . . 120.2(4) ?
C10 C11 H11 . . 119.9 ?
C12 C11 H11 . . 119.9 ?
C11 C12 C13 . . 120.5(4) ?
C11 C12 H12 . . 119.8 ?
C13 C12 H12 . . 119.8 ?
C12 C13 C8 . . 121.1(4) ?
C12 C13 H13 . . 119.4 ?
C8 C13 H13 . . 119.4 ?
C6 C14 C15 . . 126.6(3) ?
C6 C14 H14 . . 116.7 ?
C15 C14 H14 . . 116.7 ?
C16 C15 C20 . . 116.0(3) ?
C16 C15 C14 . . 122.0(3) ?
C20 C15 C14 . . 121.9(3) ?
C17 C16 C15 . . 122.4(3) ?
C17 C16 Cl2 . . 118.3(3) ?
C15 C16 Cl2 . . 119.3(3) ?
C18 C17 C16 . . 119.6(3) ?
C18 C17 H17 . . 120.2 ?
C16 C17 H17 . . 120.2 ?
C17 C18 C19 . . 119.7(3) ?
C17 C18 H18 . . 120.2 ?
C19 C18 H18 . . 120.2 ?
C20 C19 C18 . . 120.2(4) ?
C20 C19 H19 . . 119.9 ?
C18 C19 H19 . . 119.9 ?
C19 C20 C15 . . 122.0(3) ?
C19 C20 H20 . . 119.0 ?
C15 C20 H20 . . 119.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C9 . 1.739(4) ?
Cl2 C16 . 1.738(3) ?
O1 C1 . 1.228(3) ?
C1 C6 . 1.496(4) ?
C1 C2 . 1.511(4) ?
C2 C7 . 1.340(4) ?
C2 C3 . 1.514(4) ?
C3 C4 . 1.517(4) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C5 . 1.517(4) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.504(4) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 C14 . 1.345(4) ?
C7 C8 . 1.465(4) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.400(5) ?
C8 C13 . 1.405(5) ?
C9 C10 . 1.385(5) ?
C10 C11 . 1.372(6) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.374(6) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.379(5) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 C15 . 1.467(4) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.395(4) ?
C15 C20 . 1.400(4) ?
C16 C17 . 1.381(5) ?
C17 C18 . 1.376(5) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.378(5) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.374(5) ?
C19 H19 . 0.9300 ?
C20 H20 . 0.9300 ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cl1 O1 3.213(3) . 3_755 y
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
C20 H20 O1 8_755 0.93 2.51 3.352(4) 151.3
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 1375691
