#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/12/2221208.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_2221208
loop_
_publ_author_name
'Ahn, Paul D.'
'Bishop, Roger'
'Craig, Donald C.'
'Scudder, Marcia L.'
_publ_section_title
;
 1,4-Dichloronaphthalene-2,3-diol
;
_journal_coeditor_code           TK2370
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o636
_journal_paper_doi               10.1107/S1600536809004310
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C10 H6 Cl2 O2'
_chemical_formula_moiety         'C10 H6 Cl2 O2'
_chemical_formula_sum            'C10 H6 Cl2 O2'
_chemical_formula_weight         229.1
_chemical_name_systematic
;
1,4-Dichloronaphthalene-2,3-diol
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_type_scat_source
'International Tables for X-ray Crystallography, Vol. IV'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0037(4)
_cell_length_b                   11.5890(10)
_cell_length_c                   15.546(2)
_cell_measurement_reflns_used    10
_cell_measurement_temperature    294
_cell_measurement_theta_max      30
_cell_measurement_theta_min      25
_cell_volume                     901.48(16)
_computing_cell_refinement       'CAD-4 Manual (Schagen et al.,  1989)'
_computing_data_collection       'CAD-4 Manual (Schagen et al.,  1989)'
_computing_data_reduction        'local program'
_computing_molecular_graphics    'ORTEPII (Farrugia, 1997)'
_computing_publication_material  'local programs'
_computing_structure_refinement  'RAELS (Rae, 2000)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω--2θ
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1022
_diffrn_reflns_theta_full        70
_diffrn_reflns_theta_max         70
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  30
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    6.239
_exptl_absorpt_correction_T_max  0.65
_exptl_absorpt_correction_T_min  0.32
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(de Meulenaer & Tompa, 1965)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.69
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             464.0
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.17
_refine_ls_abs_structure_details
;
Flack (1983), 0 Friedel pairs
;
_refine_ls_abs_structure_Flack   0.020(10)
_refine_ls_extinction_coef       1.30(10)
_refine_ls_extinction_method     '(Coppens & Hamilton, 1970)'
_refine_ls_goodness_of_fit_ref   1.38
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1022
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.022
_refine_ls_shift/su_max          0.007
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[σ²(F) + 0.0004F²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.034
_reflns_number_gt                958
_reflns_number_total             1022
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2370.cif
_cod_data_source_block           I
_cod_original_cell_volume        901.5(2)
_cod_database_code               2221208
_cod_database_fobs_code          2221208
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'1/2-x, -y, 1/2+z'
'1/2+x, 1/2-y, -z'
'-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_occupancy
Cl Cl1 0.40159(14) 0.04588(5) 0.59724(4) 0.0414(2) Uani 1.0
Cl Cl2 1.16627(13) 0.32908(5) 0.83291(4) 0.0412(2) Uani 1.0
O O1 0.8036(4) 0.21135(16) 0.54315(9) 0.0402(4) Uani 1.0
O O2 1.1352(4) 0.3308(2) 0.64200(10) 0.0424(5) Uani 1.0
C C1 0.6113(5) 0.1220(2) 0.6655(2) 0.0290(5) Uani 1.0
C C2 0.5913(5) 0.1058(2) 0.75650(10) 0.0293(5) Uani 1.0
C C3 0.4048(6) 0.0300(2) 0.7943(2) 0.0344(5) Uani 1.0
C C4 0.3944(6) 0.0166(2) 0.8827(2) 0.0408(6) Uani 1.0
C C5 0.5719(7) 0.0785(2) 0.9350(2) 0.0435(6) Uani 1.0
C C6 0.7518(6) 0.1537(2) 0.90100(10) 0.0376(6) Uani 1.0
C C7 0.7679(5) 0.1700(2) 0.81020(10) 0.0300(5) Uani 1.0
C C8 0.9496(5) 0.2466(2) 0.7716(2) 0.0308(5) Uani 1.0
C C9 0.9652(5) 0.2599(2) 0.6839(2) 0.0306(5) Uani 1.0
C C10 0.7904(5) 0.1964(2) 0.62980(10) 0.0303(5) Uani 1.0
H H1O1 0.9726 0.2478 0.5221 0.040 Uani 1.0
H H1O2 1.2704 0.3699 0.6793 0.042 Uani 1.0
H H3 0.2790 -0.0145 0.7569 0.034 Uani 1.0
H H4 0.2609 -0.0369 0.9091 0.041 Uani 1.0
H H5 0.5660 0.0671 0.9987 0.043 Uani 1.0
H H6 0.8737 0.1979 0.9400 0.038 Uani 1.0
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Cl1 C1 C2 1_555 1_555 1_555 119.7(2) no
Cl1 C1 C10 1_555 1_555 1_555 118.1(2) no
C2 C1 C10 1_555 1_555 1_555 122.2(2) no
C1 C2 C3 1_555 1_555 1_555 122.7(2) no
C1 C2 C7 1_555 1_555 1_555 117.8(2) no
C3 C2 C7 1_555 1_555 1_555 119.5(2) no
C2 C3 C4 1_555 1_555 1_555 120.5(2) no
C3 C4 C5 1_555 1_555 1_555 119.7(3) no
C4 C5 C6 1_555 1_555 1_555 121.5(2) no
C5 C6 C7 1_555 1_555 1_555 120.4(2) no
C2 C7 C6 1_555 1_555 1_555 118.4(2) no
C2 C7 C8 1_555 1_555 1_555 118.8(2) no
C6 C7 C8 1_555 1_555 1_555 122.9(2) no
Cl2 C8 C7 1_555 1_555 1_555 121.2(2) no
Cl2 C8 C9 1_555 1_555 1_555 116.7(2) no
C7 C8 C9 1_555 1_555 1_555 122.1(2) no
O2 C9 C8 1_555 1_555 1_555 125.7(2) no
O2 C9 C10 1_555 1_555 1_555 114.7(2) no
C8 C9 C10 1_555 1_555 1_555 119.6(2) no
O1 C10 C1 1_555 1_555 1_555 121.1(2) no
O1 C10 C9 1_555 1_555 1_555 119.4(2) no
C1 C10 C9 1_555 1_555 1_555 119.6(2) no
C10 O1 H1O1 1_555 1_555 1_555 114.8 no
C9 O2 H1O2 1_555 1_555 1_555 115.0 no
C4 C3 H3 1_555 1_555 1_555 119.7 no
C2 C3 H3 1_555 1_555 1_555 119.7 no
C3 C4 H4 1_555 1_555 1_555 120.2 no
C5 C4 H4 1_555 1_555 1_555 120.2 no
C4 C5 H5 1_555 1_555 1_555 119.3 no
C6 C5 H5 1_555 1_555 1_555 119.3 no
C5 C6 H6 1_555 1_555 1_555 119.7 no
C7 C6 H6 1_555 1_555 1_555 119.9 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 1_555 1_555 1.734(2) no
Cl2 C8 1_555 1_555 1.731(2) no
O1 C10 1_555 1_555 1.361(2) no
O2 C9 1_555 1_555 1.350(3) no
C1 C2 1_555 1_555 1.431(3) no
C1 C10 1_555 1_555 1.361(3) no
C2 C3 1_555 1_555 1.410(3) no
C2 C7 1_555 1_555 1.426(3) no
C3 C4 1_555 1_555 1.385(3) no
C4 C5 1_555 1_555 1.401(4) no
C5 C6 1_555 1_555 1.360(4) no
C6 C7 1_555 1_555 1.427(3) no
C7 C8 1_555 1_555 1.405(3) no
C8 C9 1_555 1_555 1.374(3) no
C9 C10 1_555 1_555 1.419(3) no
O1 H1O1 1_555 1_555 1.000 no
O2 H1O2 1_555 1_555 1.000 no
C3 H3 1_555 1_555 1.000 no
C4 H4 1_555 1_555 1.000 no
C5 H5 1_555 1_555 1.000 no
C6 H6 1_555 1_555 1.000 no
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
O1 H1O1 O1 3_556 1.00 2.00 2.977(3) 165
