#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/25/8102596.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8102596
loop_
_publ_author_name
'Chenzhong Cao'
'Yueping Shan'
_publ_section_title
;
 Crystal structure of 2,2-bis(4-chlorophenoxy)benzo[d][1,3]dioxole,
 C19H12Cl2O4
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              723
_journal_volume                  224
_journal_year                    2009
_chemical_formula_sum            'C19 H12 Cl2 O4'
_chemical_formula_weight         375.19
_chemical_name_systematic
; 
2,2-bis(4-chlorophenoxy)benzo[d][1,3]dioxole, 
  C₁₉H₁₂Cl₂O₄ 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.3193(6)
_cell_length_b                   10.1109(10)
_cell_length_c                   26.565(3)
_cell_measurement_reflns_used    3478
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.84
_cell_measurement_theta_min      2.53
_cell_volume                     1697.3(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9745
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.403
_exptl_absorpt_correction_T_max  0.8520
_exptl_absorpt_correction_T_min  0.8237
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.41
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_coef       0.0426(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3339
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0291
_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)+(0.0322P)²+0.1184P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0668
_refine_ls_wR_factor_ref         0.0709
_reflns_number_gt                2794
_reflns_number_total             3339
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2823.cff
_cod_data_source_block           zzc1_0m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               8102596
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_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
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4936(3) 0.10920(18) 0.30479(7) 0.0586(5) Uani 1 1 d . . .
C2 C 0.5120(4) 0.2214(2) 0.27628(8) 0.0706(6) Uani 1 1 d . . .
H2 H 0.6327 0.2738 0.2783 0.085 Uiso 1 1 calc R . .
C3 C 0.3480(4) 0.2554(2) 0.24448(8) 0.0699(6) Uani 1 1 d . . .
H3 H 0.3583 0.3316 0.2250 0.084 Uiso 1 1 calc R . .
C4 C 0.1717(3) 0.17902(17) 0.24121(7) 0.0544(4) Uani 1 1 d . . .
C5 C 0.1547(3) 0.0657(2) 0.26940(8) 0.0642(5) Uani 1 1 d . . .
H5 H 0.0347 0.0129 0.2670 0.077 Uiso 1 1 calc R . .
C6 C 0.3175(4) 0.0312(2) 0.30125(8) 0.0665(5) Uani 1 1 d . . .
H6 H 0.3077 -0.0455 0.3204 0.080 Uiso 1 1 calc R . .
C7 C -0.0503(3) 0.15538(18) 0.16965(7) 0.0575(5) Uani 1 1 d . . .
C8 C -0.2130(3) -0.04397(18) 0.14571(7) 0.0536(4) Uani 1 1 d . . .
C9 C -0.0851(3) -0.14524(18) 0.12978(7) 0.0579(5) Uani 1 1 d . . .
H9 H 0.0498 -0.1552 0.1432 0.069 Uiso 1 1 calc R . .
C10 C -0.1575(3) -0.23180(19) 0.09386(8) 0.0629(5) Uani 1 1 d . . .
H10 H -0.0717 -0.3003 0.0825 0.075 Uiso 1 1 calc R . .
C11 C -0.3585(3) -0.2158(2) 0.07490(7) 0.0618(5) Uani 1 1 d . . .
C12 C -0.4875(3) -0.1162(2) 0.09147(8) 0.0697(6) Uani 1 1 d . . .
H12 H -0.6234 -0.1067 0.0785 0.084 Uiso 1 1 calc R . .
C13 C -0.4138(3) -0.0304(2) 0.12744(8) 0.0667(5) Uani 1 1 d . . .
H13 H -0.5005 0.0370 0.1394 0.080 Uiso 1 1 calc R . .
C14 C 0.1175(3) 0.22592(17) 0.10108(7) 0.0559(5) Uani 1 1 d . . .
C15 C 0.2669(3) 0.2560(2) 0.06597(8) 0.0696(6) Uani 1 1 d . . .
H15 H 0.3964 0.2124 0.0645 0.083 Uiso 1 1 calc R . .
C16 C 0.2129(5) 0.3562(3) 0.03246(9) 0.0868(8) Uani 1 1 d . . .
H16 H 0.3089 0.3805 0.0076 0.104 Uiso 1 1 calc R . .
C17 C 0.0218(5) 0.4200(2) 0.03512(9) 0.0869(7) Uani 1 1 d . . .
H17 H -0.0075 0.4870 0.0122 0.104 Uiso 1 1 calc R . .
C18 C -0.1299(4) 0.3875(2) 0.07119(8) 0.0724(6) Uani 1 1 d . . .
H18 H -0.2601 0.4301 0.0731 0.087 Uiso 1 1 calc R . .
C19 C -0.0737(3) 0.28865(17) 0.10350(7) 0.0568(5) Uani 1 1 d . . .
Cl1 Cl 0.69198(10) 0.06559(6) 0.34667(2) 0.0835(2) Uani 1 1 d . . .
Cl2 Cl -0.45014(11) -0.32420(6) 0.02916(2) 0.0914(2) Uani 1 1 d . . .
O1 O 0.0046(2) 0.22606(12) 0.21185(5) 0.0638(3) Uani 1 1 d . . .
O2 O -0.1417(2) 0.03968(12) 0.18419(5) 0.0610(3) Uani 1 1 d . . .
O3 O -0.1909(2) 0.23562(12) 0.14239(5) 0.0633(4) Uani 1 1 d . . .
O4 O 0.12770(19) 0.13187(12) 0.13836(5) 0.0591(3) Uani 1 1 d . . .
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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.6(2) . . ?
C6 C1 Cl1 119.08(15) . . ?
C2 C1 Cl1 120.28(17) . . ?
C1 C2 C3 118.7(2) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 120.91(18) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 120.25(19) . . ?
C3 C4 O1 117.53(17) . . ?
C5 C4 O1 121.99(18) . . ?
C4 C5 C6 119.21(19) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C5 120.28(18) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
O2 C7 O1 108.84(15) . . ?
O2 C7 O3 112.01(15) . . ?
O1 C7 O3 106.27(14) . . ?
O2 C7 O4 111.02(13) . . ?
O1 C7 O4 111.38(15) . . ?
O3 C7 O4 107.23(14) . . ?
C13 C8 C9 120.9(2) . . ?
C13 C8 O2 119.83(18) . . ?
C9 C8 O2 119.10(16) . . ?
C8 C9 C10 119.62(18) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C11 119.13(19) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C12 C11 C10 121.2(2) . . ?
C12 C11 Cl2 119.41(16) . . ?
C10 C11 Cl2 119.35(17) . . ?
C11 C12 C13 119.14(19) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C8 C13 C12 120.0(2) . . ?
C8 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C19 122.82(19) . . ?
C15 C14 O4 128.00(19) . . ?
C19 C14 O4 109.18(16) . . ?
C14 C15 C16 115.5(2) . . ?
C14 C15 H15 122.2 . . ?
C16 C15 H15 122.2 . . ?
C17 C16 C15 121.7(2) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C16 C17 C18 122.0(2) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 H17 119.0 . . ?
C19 C18 C17 115.2(2) . . ?
C19 C18 H18 122.4 . . ?
C17 C18 H18 122.4 . . ?
C18 C19 C14 122.7(2) . . ?
C18 C19 O3 128.00(19) . . ?
C14 C19 O3 109.25(16) . . ?
C7 O1 C4 118.02(13) . . ?
C7 O2 C8 116.64(14) . . ?
C19 O3 C7 105.73(13) . . ?
C14 O4 C7 105.62(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.367(3) . ?
C1 C2 1.369(3) . ?
C1 Cl1 1.733(2) . ?
C2 C3 1.381(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.358(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(3) . ?
C4 O1 1.396(2) . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O2 1.361(2) . ?
C7 O1 1.374(2) . ?
C7 O3 1.404(2) . ?
C7 O4 1.419(2) . ?
C8 C13 1.365(3) . ?
C8 C9 1.371(2) . ?
C8 O2 1.401(2) . ?
C9 C10 1.373(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.376(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(3) . ?
C11 Cl2 1.736(2) . ?
C12 C13 1.372(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.361(3) . ?
C14 C19 1.366(3) . ?
C14 O4 1.374(2) . ?
C15 C16 1.391(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.395(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.365(3) . ?
C18 H18 0.9300 . ?
C19 O3 1.380(2) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.0(3) . . . . ?
Cl1 C1 C2 C3 -177.97(16) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C2 C3 C4 O1 174.17(18) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
O1 C4 C5 C6 -173.87(18) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
Cl1 C1 C6 C5 178.04(16) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C13 C8 C9 C10 2.0(3) . . . . ?
O2 C8 C9 C10 176.80(16) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C9 C10 C11 Cl2 179.56(15) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
Cl2 C11 C12 C13 -179.67(15) . . . . ?
C9 C8 C13 C12 -2.1(3) . . . . ?
O2 C8 C13 C12 -176.88(17) . . . . ?
C11 C12 C13 C8 0.9(3) . . . . ?
C19 C14 C15 C16 0.3(3) . . . . ?
O4 C14 C15 C16 179.73(18) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
C15 C16 C17 C18 -0.6(4) . . . . ?
C16 C17 C18 C19 0.3(3) . . . . ?
C17 C18 C19 C14 0.3(3) . . . . ?
C17 C18 C19 O3 -179.58(18) . . . . ?
C15 C14 C19 C18 -0.6(3) . . . . ?
O4 C14 C19 C18 179.90(17) . . . . ?
C15 C14 C19 O3 179.25(17) . . . . ?
O4 C14 C19 O3 -0.2(2) . . . . ?
O2 C7 O1 C4 70.25(19) . . . . ?
O3 C7 O1 C4 -168.94(14) . . . . ?
O4 C7 O1 C4 -52.5(2) . . . . ?
C3 C4 O1 C7 115.6(2) . . . . ?
C5 C4 O1 C7 -69.9(2) . . . . ?
O1 C7 O2 C8 178.43(14) . . . . ?
O3 C7 O2 C8 61.21(19) . . . . ?
O4 C7 O2 C8 -58.63(19) . . . . ?
C13 C8 O2 C7 -88.8(2) . . . . ?
C9 C8 O2 C7 96.35(19) . . . . ?
C18 C19 O3 C7 -169.41(19) . . . . ?
C14 C19 O3 C7 10.74(19) . . . . ?
O2 C7 O3 C19 -138.95(15) . . . . ?
O1 C7 O3 C19 102.31(16) . . . . ?
O4 C7 O3 C19 -16.91(18) . . . . ?
C15 C14 O4 C7 170.29(19) . . . . ?
C19 C14 O4 C7 -10.25(18) . . . . ?
O2 C7 O4 C14 139.45(15) . . . . ?
O1 C7 O4 C14 -99.09(16) . . . . ?
O3 C7 O4 C14 16.79(18) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653980
