#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/36/2213646.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_2213646
loop_
_publ_author_name
'Huan-Mei Guo'
_publ_section_title
;
 3,4-Dichlorohypnone
;
_journal_coeditor_code           AT2284
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2812
_journal_page_last               o2812
_journal_paper_doi               10.1107/S1600536807021356
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C8 H6 Cl2 O'
_chemical_formula_moiety         'C8 H6 Cl2 O'
_chemical_formula_sum            'C8 H6 Cl2 O'
_chemical_formula_weight         189.03
_chemical_name_systematic
;
1-(3,4-dichlorophenyl)ethanone
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.717(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2878(15)
_cell_length_b                   10.597(2)
_cell_length_c                   10.610(2)
_cell_measurement_reflns_used    3035
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.44
_cell_measurement_theta_min      2.87
_cell_volume                     799.3(3)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4489
_diffrn_reflns_theta_full        26.44
_diffrn_reflns_theta_max         26.44
_diffrn_reflns_theta_min         2.75
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.743
_exptl_absorpt_correction_T_max  0.8904
_exptl_absorpt_correction_T_min  0.8657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.291
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1637
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0326
_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)+(0.0506P)²+0.2513P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0938
_reflns_number_gt                1449
_reflns_number_total             1637
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2284.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2213646
_cod_database_fobs_code          2213646
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
Cl Cl1 0.09028(8) 0.22661(5) 0.39055(6) 0.06076(19) Uani d . 1
Cl Cl2 0.12712(9) 0.44153(5) 0.19719(5) 0.0671(2) Uani d . 1
O O1 0.4462(2) 0.73876(15) 0.70133(14) 0.0665(4) Uani d . 1
C C1 0.2990(2) 0.50645(18) 0.61880(17) 0.0466(4) Uani d . 1
H H1 0.3372 0.5199 0.7073 0.056 Uiso calc R 1
C C2 0.2314(3) 0.39160(18) 0.57462(18) 0.0495(4) Uani d . 1
H H2 0.2227 0.3271 0.6325 0.059 Uiso calc R 1
C C3 0.1763(2) 0.37135(16) 0.44448(18) 0.0421(4) Uani d . 1
C C4 0.1904(2) 0.46613(16) 0.35993(16) 0.0409(4) Uani d . 1
C C5 0.2580(2) 0.58170(16) 0.40441(16) 0.0409(4) Uani d . 1
H H5 0.2675 0.6458 0.3464 0.049 Uiso calc R 1
C C6 0.3120(2) 0.60317(16) 0.53495(16) 0.0383(4) Uani d . 1
C C7 0.3855(2) 0.72665(17) 0.58718(18) 0.0462(4) Uani d . 1
C C8 0.3836(4) 0.83410(19) 0.4994(2) 0.0637(5) Uani d . 1
H H8A 0.4336 0.9073 0.5485 0.096 Uiso calc R 1
H H8B 0.2567 0.8507 0.4540 0.096 Uiso calc R 1
H H8C 0.4592 0.8146 0.4385 0.096 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0682(3) 0.0402(3) 0.0742(4) -0.0130(2) 0.0164(3) -0.0048(2)
Cl2 0.1019(4) 0.0493(3) 0.0420(3) -0.0029(2) -0.0015(2) -0.00618(19)
O1 0.0833(10) 0.0658(10) 0.0479(8) -0.0126(8) 0.0089(7) -0.0161(7)
C1 0.0508(9) 0.0526(10) 0.0374(8) -0.0012(8) 0.0117(7) 0.0003(7)
C2 0.0566(10) 0.0464(10) 0.0486(10) -0.0027(8) 0.0182(8) 0.0091(8)
C3 0.0387(8) 0.0353(8) 0.0540(10) -0.0018(6) 0.0138(7) -0.0021(7)
C4 0.0432(8) 0.0399(9) 0.0385(8) 0.0028(7) 0.0065(7) -0.0021(7)
C5 0.0460(9) 0.0363(8) 0.0403(9) 0.0011(7) 0.0095(7) 0.0014(7)
C6 0.0362(8) 0.0406(9) 0.0398(8) 0.0017(6) 0.0122(6) -0.0022(7)
C7 0.0469(9) 0.0463(10) 0.0471(10) -0.0023(7) 0.0139(8) -0.0109(8)
C8 0.0870(15) 0.0401(10) 0.0653(13) -0.0095(10) 0.0195(11) -0.0077(9)
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
C2 C1 C6 121.12(17)
C2 C1 H1 119.4
C6 C1 H1 119.4
C1 C2 C3 119.55(17)
C1 C2 H2 120.2
C3 C2 H2 120.2
C4 C3 C2 120.00(16)
C4 C3 Cl1 121.05(14)
C2 C3 Cl1 118.95(14)
C5 C4 C3 120.43(16)
C5 C4 Cl2 118.92(14)
C3 C4 Cl2 120.65(14)
C4 C5 C6 119.93(16)
C4 C5 H5 120.0
C6 C5 H5 120.0
C5 C6 C1 118.97(16)
C5 C6 C7 121.72(16)
C1 C6 C7 119.31(15)
O1 C7 C8 120.41(18)
O1 C7 C6 119.75(17)
C8 C7 C6 119.84(16)
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C3 1.7072(17)
Cl2 C4 1.7063(17)
O1 C7 1.201(2)
C1 C2 1.357(3)
C1 C6 1.374(3)
C1 H1 0.9300
C2 C3 1.367(3)
C2 H2 0.9300
C3 C4 1.366(2)
C4 C5 1.365(2)
C5 C6 1.373(2)
C5 H5 0.9300
C6 C7 1.475(2)
C7 C8 1.469(3)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
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 0.4(3)
C1 C2 C3 C4 0.4(3)
C1 C2 C3 Cl1 -179.62(14)
C2 C3 C4 C5 -0.5(3)
Cl1 C3 C4 C5 179.49(13)
C2 C3 C4 Cl2 178.55(14)
Cl1 C3 C4 Cl2 -1.4(2)
C3 C4 C5 C6 -0.1(3)
Cl2 C4 C5 C6 -179.19(12)
C4 C5 C6 C1 0.9(2)
C4 C5 C6 C7 -179.87(15)
C2 C1 C6 C5 -1.0(3)
C2 C1 C6 C7 179.71(16)
C5 C6 C7 O1 -173.66(17)
C1 C6 C7 O1 5.6(3)
C5 C6 C7 C8 6.5(3)
C1 C6 C7 C8 -174.27(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 68350
