#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:28:26 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201972 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/49/2104977.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_2104977
loop_
_publ_author_name
'Solanko, Katarzyna A.'
'Bond, Andrew D.'
_publ_section_title
;
 Intermolecular interactions and unexpected isostructurality in the
 crystal structures of the dichlorobenzaldehyde isomers
;
_journal_coeditor_code           GP5044
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              437
_journal_page_last               445
_journal_paper_doi               10.1107/S0108768111035786
_journal_volume                  67
_journal_year                    2011
_chemical_formula_moiety         'C7 H4 Cl2 O'
_chemical_formula_sum            'C7 H4 Cl2 O'
_chemical_formula_weight         175.00
_chemical_name_common            3,5-dichlorobenzaldehyde
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 91.546(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   3.7785(5)
_cell_length_b                   31.353(5)
_cell_length_c                   12.058(2)
_cell_measurement_reflns_used    1496
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      20.83
_cell_measurement_theta_min      3.44
_cell_volume                     1428.0(4)
_computing_cell_refinement       'SAINT v.7.06a (Bruker, 2003)'
_computing_data_collection       'APEX2 v.1.0-22 (Bruker Nonius, 2004)'
_computing_data_reduction        'SAINT v.7.06a'
_computing_molecular_graphics    'SHELXTL v.6.10'
_computing_publication_material  'SHELXTL v.6.10'
_computing_structure_refinement  'SHELXTL v.6.10'
_computing_structure_solution    'SHELXTL v.6.10 (Sheldrick, 2000)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker-Nonius X8APEX-II CCD'
_diffrn_measurement_method       'thin-slice ω and φ 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  0.0689
_diffrn_reflns_av_sigmaI/netI    0.0790
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13283
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         3.62
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.824
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Ratio of minimum to maximum apparent transmission:  0.703457
 SADABS v.2.10 (Sheldrick, 2003)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.348
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0457
_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)+(0.0444P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0981
_reflns_number_gt                1731
_reflns_number_total             2678
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gp5044.cif
_cod_data_source_block           6
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2104977
_cod_database_fobs_code          2104977
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O O1 0.1658(7) 0.19259(7) 0.1451(2) 0.0285(6) Uani d . 1 1
C C1 0.4429(8) 0.17430(10) 0.3185(3) 0.0160(8) Uani d . 1 1
C C2 0.3804(9) 0.13052(10) 0.3110(3) 0.0190(8) Uani d . 1 1
H H2 0.2700 0.1185 0.2465 0.023 Uiso calc R 1 1
C C3 0.4828(9) 0.10497(10) 0.3997(3) 0.0181(8) Uani d . 1 1
Cl Cl3 0.3992(3) 0.05057(3) 0.39358(7) 0.0281(3) Uani d . 1 1
C C4 0.6462(8) 0.12155(10) 0.4943(3) 0.0179(8) Uani d . 1 1
H H4 0.7157 0.1035 0.5544 0.022 Uiso calc R 1 1
C C5 0.7057(9) 0.16505(11) 0.4991(3) 0.0170(8) Uani d . 1 1
Cl Cl5 0.9051(2) 0.18681(3) 0.61796(7) 0.0230(2) Uani d . 1 1
C C6 0.6065(9) 0.19175(11) 0.4130(3) 0.0184(8) Uani d . 1 1
H H6 0.6489 0.2216 0.4179 0.022 Uiso calc R 1 1
C C7 0.3317(9) 0.20325(11) 0.2279(3) 0.0235(9) Uani d . 1 1
H H7 0.3948 0.2325 0.2349 0.028 Uiso calc R 1 1
O O1A 0.3662(7) 0.21095(7) 0.8475(2) 0.0309(7) Uani d . 1 1
C C1A 0.5570(9) 0.14281(10) 0.9123(3) 0.0170(8) Uani d . 1 1
C C2A 0.4249(8) 0.12059(10) 0.8201(3) 0.0185(8) Uani d . 1 1
H H2A 0.3249 0.1354 0.7580 0.022 Uiso calc R 1 1
C C3A 0.4429(8) 0.07671(10) 0.8211(3) 0.0171(8) Uani d . 1 1
Cl Cl3A 0.2794(2) 0.04810(3) 0.70719(7) 0.0238(2) Uani d . 1 1
C C4A 0.5869(8) 0.05441(10) 0.9112(3) 0.0171(8) Uani d . 1 1
H H4A 0.5977 0.0241 0.9107 0.021 Uiso calc R 1 1
C C5A 0.7141(9) 0.07749(11) 1.0017(3) 0.0172(8) Uani d . 1 1
Cl Cl5A 0.8886(2) 0.05036(3) 1.11618(7) 0.0224(2) Uani d . 1 1
C C6A 0.7031(8) 0.12161(10) 1.0033(3) 0.0178(8) Uani d . 1 1
H H6A 0.7940 0.1370 1.0656 0.021 Uiso calc R 1 1
C C7A 0.5342(9) 0.19001(11) 0.9146(3) 0.0223(9) Uani d . 1 1
H H7A 0.6592 0.2047 0.9724 0.027 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'
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
C6 C1 C2 120.7(3)
C6 C1 C7 118.4(3)
C2 C1 C7 120.9(3)
C3 C2 C1 118.4(3)
C3 C2 H2 120.8
C1 C2 H2 120.8
C2 C3 C4 122.0(3)
C2 C3 Cl3 119.3(3)
C4 C3 Cl3 118.7(3)
C5 C4 C3 118.2(3)
C5 C4 H4 120.9
C3 C4 H4 120.9
C6 C5 C4 121.8(3)
C6 C5 Cl5 119.0(3)
C4 C5 Cl5 119.2(3)
C5 C6 C1 118.9(3)
C5 C6 H6 120.6
C1 C6 H6 120.6
O1 C7 C1 124.9(3)
O1 C7 H7 117.6
C1 C7 H7 117.6
C6A C1A C2A 121.3(3)
C6A C1A C7A 119.1(3)
C2A C1A C7A 119.6(3)
C3A C2A C1A 118.4(3)
C3A C2A H2A 120.8
C1A C2A H2A 120.8
C2A C3A C4A 121.8(3)
C2A C3A Cl3A 119.5(3)
C4A C3A Cl3A 118.7(3)
C5A C4A C3A 118.3(3)
C5A C4A H4A 120.9
C3A C4A H4A 120.9
C6A C5A C4A 121.6(3)
C6A C5A Cl5A 119.3(3)
C4A C5A Cl5A 119.1(3)
C5A C6A C1A 118.7(3)
C5A C6A H6A 120.6
C1A C6A H6A 120.6
O1A C7A C1A 124.0(3)
O1A C7A H7A 118.0
C1A C7A H7A 118.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.211(4)
C1 C6 1.393(4)
C1 C2 1.395(4)
C1 C7 1.473(4)
C2 C3 1.383(4)
C2 H2 0.950
C3 C4 1.384(4)
C3 Cl3 1.736(3)
C4 C5 1.383(4)
C4 H4 0.950
C5 C6 1.378(4)
C5 Cl5 1.741(3)
C6 H6 0.950
C7 H7 0.950
O1A C7A 1.209(4)
C1A C6A 1.385(4)
C1A C2A 1.394(4)
C1A C7A 1.483(4)
C2A C3A 1.378(4)
C2A H2A 0.950
C3A C4A 1.391(4)
C3A Cl3A 1.739(3)
C4A C5A 1.385(4)
C4A H4A 0.950
C5A C6A 1.384(4)
C5A Cl5A 1.736(3)
C6A H6A 0.950
C7A H7A 0.950
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(5)
C7 C1 C2 C3 -178.5(3)
C1 C2 C3 C4 -0.4(5)
C1 C2 C3 Cl3 178.6(2)
C2 C3 C4 C5 0.2(5)
Cl3 C3 C4 C5 -178.8(2)
C3 C4 C5 C6 0.1(5)
C3 C4 C5 Cl5 179.1(2)
C4 C5 C6 C1 -0.2(5)
Cl5 C5 C6 C1 -179.2(3)
C2 C1 C6 C5 0.0(5)
C7 C1 C6 C5 178.8(3)
C6 C1 C7 O1 -174.6(3)
C2 C1 C7 O1 4.2(6)
C6A C1A C2A C3A -0.1(5)
C7A C1A C2A C3A -178.7(3)
C1A C2A C3A C4A 0.2(5)
C1A C2A C3A Cl3A 179.9(2)
C2A C3A C4A C5A 0.1(5)
Cl3A C3A C4A C5A -179.6(3)
C3A C4A C5A C6A -0.6(5)
C3A C4A C5A Cl5A 179.0(2)
C4A C5A C6A C1A 0.8(5)
Cl5A C5A C6A C1A -178.8(2)
C2A C1A C6A C5A -0.4(5)
C7A C1A C6A C5A 178.2(3)
C6A C1A C7A O1A -168.6(3)
C2A C1A C7A O1A 10.0(5)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 32882
