#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/49/2104975.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_2104975
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            2,5-dichlorobenzaldehyde
_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                89.091(5)
_cell_angle_beta                 85.728(5)
_cell_angle_gamma                81.115(5)
_cell_formula_units_Z            3
_cell_length_a                   3.8150(5)
_cell_length_b                   7.8290(11)
_cell_length_c                   17.895(3)
_cell_measurement_reflns_used    1343
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      24.12
_cell_measurement_theta_min      2.87
_cell_volume                     526.60(13)
_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 0.967
_diffrn_measured_fraction_theta_max 0.967
_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  0.0468
_diffrn_reflns_av_sigmaI/netI    0.0663
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6319
_diffrn_reflns_theta_full        25.12
_diffrn_reflns_theta_max         25.12
_diffrn_reflns_theta_min         4.31
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.838
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS v.2.10 (Sheldrick, 2003)
 Ratio of minimum to maximum apparent transmission:  0.721852
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.299
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1827
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0339P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0806
_reflns_number_gt                1313
_reflns_number_total             1827
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gp5044.cif
_cod_data_source_block           3
_cod_database_code               2104975
_cod_database_fobs_code          2104975
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.2055(5) 1.2310(2) 0.18353(11) 0.0278(5) Uani d . 1 1 . .
C C1 0.0282(7) 0.9539(3) 0.18013(16) 0.0159(7) Uani d . 1 1 . .
C C2 -0.1146(7) 0.8213(4) 0.21890(16) 0.0162(7) Uani d . 1 1 . .
Cl Cl2 -0.30351(19) 0.85462(10) 0.31062(4) 0.0255(2) Uani d . 1 1 . .
C C3 -0.1086(7) 0.6606(3) 0.18701(17) 0.0183(7) Uani d . 1 1 . .
H H3 -0.2003 0.5710 0.2149 0.022 Uiso calc R 1 1 . .
C C4 0.0317(7) 0.6327(4) 0.11464(17) 0.0190(7) Uani d . 1 1 . .
H H4 0.0347 0.5236 0.0920 0.023 Uiso calc R 1 1 . .
C C5 0.1685(7) 0.7627(3) 0.07462(15) 0.0141(7) Uani d . 1 1 . .
Cl Cl5 0.34316(19) 0.72875(9) -0.01745(4) 0.0196(2) Uani d . 1 1 . .
C C6 0.1683(7) 0.9211(4) 0.10660(16) 0.0167(7) Uani d . 1 1 . .
H H6 0.2644 1.0091 0.0784 0.020 Uiso calc R 1 1 . .
C C7 0.0427(8) 1.1240(4) 0.21324(17) 0.0215(7) Uani d . 1 1 . .
H H7 -0.0827 1.1511 0.2605 0.026 Uiso calc R 1 1 . .
O O1A 0.0815(13) 0.9457(5) 0.5114(3) 0.0444(13) Uani d P 0.50 1 . 1
C C7A 0.2594(15) 0.8383(8) 0.5478(3) 0.0272(16) Uani d P 0.50 1 A 1
H H7A 0.3169 0.8724 0.5955 0.033 Uiso calc PR 0.50 1 A 1
H H4A 0.3142 0.7827 0.5433 0.033 Uiso d PR 0.50 1 A 2
C C1A 0.3878(7) 0.6681(4) 0.52552(17) 0.0208(7) Uani d . 1 1 . .
C C2A 0.5752(7) 0.5422(4) 0.57071(16) 0.0209(7) Uani d . 1 1 A .
Cl Cl2A 0.6697(2) 0.59588(10) 0.66033(4) 0.0281(2) Uani d . 1 1 . .
C C3A 0.6859(7) 0.3776(4) 0.54496(17) 0.0214(7) Uani d . 1 1 . .
H H3A 0.8143 0.2943 0.5759 0.026 Uiso calc R 1 1 A .
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
C6 C1 C2 . . 117.6(2)
C6 C1 C7 . . 118.9(2)
C2 C1 C7 . . 123.5(3)
C3 C2 C1 . . 121.8(3)
C3 C2 Cl2 . . 118.1(2)
C1 C2 Cl2 . . 120.1(2)
C4 C3 C2 . . 119.1(2)
C4 C3 H3 . . 120.5
C2 C3 H3 . . 120.5
C3 C4 C5 . . 120.2(3)
C3 C4 H4 . . 119.9
C5 C4 H4 . . 119.9
C6 C5 C4 . . 120.7(3)
C6 C5 Cl5 . . 118.8(2)
C4 C5 Cl5 . . 120.4(2)
C5 C6 C1 . . 120.6(2)
C5 C6 H6 . . 119.7
C1 C6 H6 . . 119.7
O1 C7 C1 . . 123.7(3)
O1 C7 H7 . . 118.2
C1 C7 H7 . . 118.2
O1A C7A C1A . . 125.5(6)
O1A C7A H7A . . 117.2
C1A C7A H7A . . 117.2
C3A C1A C7A 2_666 . 116.6(4)
C3A C1A C2A 2_666 . 118.8(3)
C7A C1A C2A . . 124.5(4)
C3A C1A H4A 2_666 . 120.7
C2A C1A H4A . . 120.5
C3A C2A C1A . . 120.7(3)
C3A C2A Cl2A . . 119.4(2)
C1A C2A Cl2A . . 119.9(2)
C2A C3A C1A . 2_666 120.4(3)
C2A C3A H3A . . 119.8
C1A C3A H3A 2_666 . 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C7 . 1.212(3)
C1 C6 . 1.395(4)
C1 C2 . 1.397(4)
C1 C7 . 1.477(4)
C2 C3 . 1.386(4)
C2 Cl2 . 1.750(3)
C3 C4 . 1.372(4)
C3 H3 . 0.950
C4 C5 . 1.381(4)
C4 H4 . 0.950
C5 C6 . 1.374(4)
C5 Cl5 . 1.739(3)
C6 H6 . 0.950
C7 H7 . 0.950
O1A C7A . 1.210(6)
C7A C1A . 1.400(6)
C7A H7A . 0.950
C1A C3A 2_666 1.377(4)
C1A C2A . 1.407(4)
C1A H4A . 0.950
C2A C3A . 1.369(4)
C2A Cl2A . 1.741(3)
C3A C1A 2_666 1.377(4)
C3A H3A . 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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C6 C1 C2 C3 . . 2.0(4)
C7 C1 C2 C3 . . -177.0(3)
C6 C1 C2 Cl2 . . -178.6(2)
C7 C1 C2 Cl2 . . 2.3(4)
C1 C2 C3 C4 . . -2.0(4)
Cl2 C2 C3 C4 . . 178.7(2)
C2 C3 C4 C5 . . 0.8(4)
C3 C4 C5 C6 . . 0.4(4)
C3 C4 C5 Cl5 . . -179.4(2)
C4 C5 C6 C1 . . -0.3(4)
Cl5 C5 C6 C1 . . 179.5(2)
C2 C1 C6 C5 . . -0.9(4)
C7 C1 C6 C5 . . 178.2(3)
C6 C1 C7 O1 . . -8.8(4)
C2 C1 C7 O1 . . 170.2(3)
O1A C7A C1A C3A . 2_666 2.4(7)
O1A C7A C1A C2A . . -175.8(5)
C3A C1A C2A C3A 2_666 . 0.6(5)
C7A C1A C2A C3A . . 178.8(3)
C3A C1A C2A Cl2A 2_666 . -179.6(2)
C7A C1A C2A Cl2A . . -1.4(5)
C1A C2A C3A C1A . 2_666 -0.6(5)
Cl2A C2A C3A C1A . 2_666 179.6(2)
