#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/89/2228987.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_2228987
loop_
_publ_author_name
'Devarajegowda, H. C.'
'Nagendra, P.'
'Jeyaseelan, S.'
'Chidananda, N.'
'Poojary, Boja'
_publ_section_title
;
 1-Chloro-4-(3,4-dichlorophenyl)-3,4-dihydronaphthalene-2-carbaldehyde
;
_journal_coeditor_code           BV2168
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o378
_journal_paper_doi               10.1107/S160053681100105X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C17 H11 Cl3 O'
_chemical_formula_moiety         'C17 H11 Cl3 O'
_chemical_formula_sum            'C17 H11 Cl3 O'
_chemical_formula_weight         337.61
_chemical_melting_point          383
_chemical_name_systematic
;
1-Chloro-4-(3,4-dichlorophenyl)-3,4-dihydronaphthalene-2-carbaldehyde
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 91.436(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2969(5)
_cell_length_b                   10.8849(5)
_cell_length_c                   13.6144(7)
_cell_measurement_reflns_used    3006
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.40
_cell_volume                     1525.43(13)
_computing_cell_refinement
'CrysAlis PRO CCD  (Oxford Diffraction, 2010)'
_computing_data_collection
;
CrysAlis PRO CCD (Oxford Diffraction, 2010)
;
_computing_data_reduction
'CrysAlis PRO RED (Oxford Diffraction, 2010)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et
al., 1993)
;
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0839
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15902
_diffrn_reflns_reduction_process
;
;
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.40
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'(CrysAlis PRO RED; Oxford Diffraction, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.325
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3006
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0502
_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)+(0.0885P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1494
_reflns_number_gt                2143
_reflns_number_total             3006
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bv2168.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228987
_cod_database_fobs_code          2228987
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.40177(8) 0.17987(7) 0.18417(6) 0.0642(3) Uani d . 1 . .
Cl Cl2 1.03593(8) 0.22018(9) -0.40674(6) 0.0809(3) Uani d . 1 . .
Cl Cl3 1.07383(9) 0.35613(9) -0.20272(7) 0.0853(3) Uani d . 1 . .
O O4 0.3558(2) 0.4375(2) -0.04817(19) 0.0873(8) Uani d . 1 . .
C C5 0.3745(3) 0.3618(3) 0.0142(3) 0.0654(8) Uani d . 1 . .
C C6 0.4835(3) 0.2751(2) 0.01503(19) 0.0461(6) Uani d . 1 . .
C C7 0.5053(2) 0.1922(2) 0.08561(18) 0.0410(6) Uani d . 1 . .
C C8 0.6168(2) 0.1084(2) 0.08586(17) 0.0389(6) Uani d . 1 . .
C C9 0.6561(3) 0.0405(2) 0.16846(19) 0.0474(6) Uani d . 1 . .
C C10 0.7619(3) -0.0361(3) 0.1655(2) 0.0604(8) Uani d . 1 . .
C C11 0.8291(3) -0.0479(3) 0.0801(2) 0.0595(8) Uani d . 1 . .
C C12 0.7912(3) 0.0171(2) -0.0023(2) 0.0520(7) Uani d . 1 . .
C C13 0.6860(2) 0.0965(2) -0.00149(17) 0.0409(6) Uani d . 1 . .
C C14 0.6365(3) 0.1633(2) -0.09391(19) 0.0462(6) Uani d . 1 . .
C C15 0.5787(3) 0.2861(3) -0.0664(2) 0.0539(7) Uani d . 1 . .
C C16 0.7379(2) 0.1794(2) -0.17227(19) 0.0433(6) Uani d . 1 . .
C C17 0.7223(3) 0.1248(2) -0.26254(19) 0.0447(6) Uani d . 1 . .
C C18 0.8128(3) 0.1384(2) -0.3336(2) 0.0475(6) Uani d . 1 . .
C C19 0.9213(3) 0.2083(2) -0.31643(19) 0.0451(6) Uani d . 1 . .
C C20 0.9393(3) 0.2661(2) -0.2272(2) 0.0476(6) Uani d . 1 . .
C C21 0.8493(3) 0.2513(2) -0.1548(2) 0.0503(7) Uani d . 1 . .
H H5 0.327(3) 0.359(3) 0.067(2) 0.080(11) Uiso d . 1 . .
H H9 0.616(3) 0.050(2) 0.224(2) 0.061(8) Uiso d . 1 . .
H H10 0.792(3) -0.082(3) 0.218(2) 0.088(11) Uiso d . 1 . .
H H11 0.904(3) -0.096(2) 0.0799(18) 0.050(7) Uiso d . 1 . .
H H12 0.836(3) 0.009(2) -0.054(2) 0.057(8) Uiso d . 1 . .
H H14 0.561(2) 0.111(2) -0.1275(17) 0.040(6) Uiso d . 1 . .
H H17 0.653(3) 0.068(2) -0.2739(18) 0.049(7) Uiso d . 1 . .
H H18 0.807(3) 0.103(2) -0.393(2) 0.055(8) Uiso d . 1 . .
H H15A 0.668(4) 0.339(3) -0.040(3) 0.101(12) Uiso d . 1 . .
H H15B 0.536(3) 0.324(2) -0.121(2) 0.057(8) Uiso d . 1 . .
H H21 0.867(3) 0.291(3) -0.090(2) 0.061(8) Uiso d . 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
O4 C5 C6 . . 123.9(3) ?
O4 C5 H5 . . 121(2) ?
C6 C5 H5 . . 115(2) ?
C7 C6 C5 . . 123.8(2) ?
C7 C6 C15 . . 119.0(2) ?
C5 C6 C15 . . 117.1(2) ?
C6 C7 C8 . . 122.7(2) ?
C6 C7 Cl1 . . 120.84(19) ?
C8 C7 Cl1 . . 116.44(17) ?
C9 C8 C13 . . 119.2(2) ?
C9 C8 C7 . . 122.8(2) ?
C13 C8 C7 . . 117.9(2) ?
C10 C9 C8 . . 120.8(2) ?
C10 C9 H9 . . 119.4(19) ?
C8 C9 H9 . . 119.7(19) ?
C9 C10 C11 . . 119.9(3) ?
C9 C10 H10 . . 124(2) ?
C11 C10 H10 . . 116(2) ?
C10 C11 C12 . . 120.2(3) ?
C10 C11 H11 . . 119.2(16) ?
C12 C11 H11 . . 120.4(16) ?
C11 C12 C13 . . 121.3(3) ?
C11 C12 H12 . . 117.9(19) ?
C13 C12 H12 . . 120.7(19) ?
C12 C13 C8 . . 118.5(2) ?
C12 C13 C14 . . 122.3(2) ?
C8 C13 C14 . . 119.1(2) ?
C15 C14 C16 . . 110.7(2) ?
C15 C14 C13 . . 110.0(2) ?
C16 C14 C13 . . 114.3(2) ?
C15 C14 H14 . . 106.9(12) ?
C16 C14 H14 . . 105.6(12) ?
C13 C14 H14 . . 109.1(12) ?
C6 C15 C14 . . 112.3(2) ?
C6 C15 H15A . . 110.4(19) ?
C14 C15 H15A . . 101.8(18) ?
C6 C15 H15B . . 108.2(16) ?
C14 C15 H15B . . 111.5(16) ?
H15A C15 H15B . . 113(2) ?
C17 C16 C21 . . 118.1(2) ?
C17 C16 C14 . . 120.8(2) ?
C21 C16 C14 . . 121.2(2) ?
C18 C17 C16 . . 121.4(3) ?
C18 C17 H17 . . 118.4(15) ?
C16 C17 H17 . . 119.8(15) ?
C19 C18 C17 . . 120.5(3) ?
C19 C18 H18 . . 115.4(18) ?
C17 C18 H18 . . 124.1(18) ?
C18 C19 C20 . . 119.8(2) ?
C18 C19 Cl2 . . 119.3(2) ?
C20 C19 Cl2 . . 120.9(2) ?
C19 C20 C21 . . 119.9(2) ?
C19 C20 Cl3 . . 121.4(2) ?
C21 C20 Cl3 . . 118.7(2) ?
C20 C21 C16 . . 120.3(3) ?
C20 C21 H21 . . 118.3(17) ?
C16 C21 H21 . . 121.3(17) ?
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 C7 . 1.740(2) ?
Cl2 C19 . 1.731(2) ?
Cl3 C20 . 1.722(3) ?
O4 C5 . 1.195(4) ?
C5 C6 . 1.466(4) ?
C5 H5 . 0.88(3) ?
C6 C7 . 1.333(3) ?
C6 C15 . 1.503(3) ?
C7 C8 . 1.465(3) ?
C8 C9 . 1.398(3) ?
C8 C13 . 1.408(3) ?
C9 C10 . 1.373(4) ?
C9 H9 . 0.88(3) ?
C10 C11 . 1.374(4) ?
C10 H10 . 0.92(3) ?
C11 C12 . 1.375(4) ?
C11 H11 . 0.93(3) ?
C12 C13 . 1.386(3) ?
C12 H12 . 0.86(3) ?
C13 C14 . 1.530(3) ?
C14 C15 . 1.514(4) ?
C14 C16 . 1.521(3) ?
C14 H14 . 1.06(2) ?
C15 H15A . 1.14(4) ?
C15 H15B . 0.94(3) ?
C16 C17 . 1.371(4) ?
C16 C21 . 1.404(4) ?
C17 C18 . 1.368(4) ?
C17 H17 . 0.95(3) ?
C18 C19 . 1.367(4) ?
C18 H18 . 0.89(3) ?
C19 C20 . 1.377(4) ?
C20 C21 . 1.379(4) ?
C21 H21 . 0.99(3) ?
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
C5 H5 Cl1 . 0.88(3) 2.62(3) 3.053(4) 111(2) ?
C9 H9 Cl1 . 0.88(3) 2.66(3) 3.039(3) 107(2) ?
C15 H15B O4 . 0.94(3) 2.46(3) 2.841(4) 103.8(19) ?
C18 H18 O4 2_644 0.90(3) 2.58(3) 3.201(3) 128(2) 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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O4 C5 C6 C7 . . . . 178.8(3) ?
O4 C5 C6 C15 . . . . 2.0(5) ?
C5 C6 C7 C8 . . . . -178.5(3) ?
C15 C6 C7 C8 . . . . -1.7(4) ?
C5 C6 C7 Cl1 . . . . 0.6(4) ?
C15 C6 C7 Cl1 . . . . 177.4(2) ?
C6 C7 C8 C9 . . . . 165.8(3) ?
Cl1 C7 C8 C9 . . . . -13.4(3) ?
C6 C7 C8 C13 . . . . -14.4(4) ?
Cl1 C7 C8 C13 . . . . 166.37(17) ?
C13 C8 C9 C10 . . . . 0.8(4) ?
C7 C8 C9 C10 . . . . -179.4(2) ?
C8 C9 C10 C11 . . . . -1.0(5) ?
C9 C10 C11 C12 . . . . 0.2(5) ?
C10 C11 C12 C13 . . . . 0.6(5) ?
C11 C12 C13 C8 . . . . -0.8(4) ?
C11 C12 C13 C14 . . . . -175.9(3) ?
C9 C8 C13 C12 . . . . 0.1(4) ?
C7 C8 C13 C12 . . . . -179.7(2) ?
C9 C8 C13 C14 . . . . 175.4(2) ?
C7 C8 C13 C14 . . . . -4.4(3) ?
C12 C13 C14 C15 . . . . -149.2(3) ?
C8 C13 C14 C15 . . . . 35.7(3) ?
C12 C13 C14 C16 . . . . -24.0(3) ?
C8 C13 C14 C16 . . . . 160.9(2) ?
C7 C6 C15 C14 . . . . 34.9(4) ?
C5 C6 C15 C14 . . . . -148.1(3) ?
C16 C14 C15 C6 . . . . -176.7(2) ?
C13 C14 C15 C6 . . . . -49.5(3) ?
C15 C14 C16 C17 . . . . -118.7(3) ?
C13 C14 C16 C17 . . . . 116.5(3) ?
C15 C14 C16 C21 . . . . 60.7(3) ?
C13 C14 C16 C21 . . . . -64.1(3) ?
C21 C16 C17 C18 . . . . 0.7(4) ?
C14 C16 C17 C18 . . . . -179.9(2) ?
C16 C17 C18 C19 . . . . -0.6(4) ?
C17 C18 C19 C20 . . . . -0.4(4) ?
C17 C18 C19 Cl2 . . . . 178.27(19) ?
C18 C19 C20 C21 . . . . 1.3(4) ?
Cl2 C19 C20 C21 . . . . -177.3(2) ?
C18 C19 C20 Cl3 . . . . -179.4(2) ?
Cl2 C19 C20 Cl3 . . . . 1.9(3) ?
C19 C20 C21 C16 . . . . -1.3(4) ?
Cl3 C20 C21 C16 . . . . 179.5(2) ?
C17 C16 C21 C20 . . . . 0.3(4) ?
C14 C16 C21 C20 . . . . -179.2(2) ?
