#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/01/2210152.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_2210152
loop_
_publ_author_name
'Vyas, Sandhya M.'
'Parkin, Sean'
'Robertson, Larry W.'
'Lehmler, Hans-Joachim'
_publ_section_title
;
 4-Chloro-2',3'-dimethoxybiphenyl
;
_journal_coeditor_code           CI2118
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3639
_journal_page_last               o3640
_journal_paper_doi               10.1107/S1600536806028923
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C14 H13 Cl O2'
_chemical_formula_moiety         'C14 H13 Cl O2'
_chemical_formula_sum            'C14 H13 Cl O2'
_chemical_formula_weight         248.69
_chemical_name_systematic
;
4-Chloro-2',3'-dimethoxybiphenyl
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.2829(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6579(2)
_cell_length_b                   13.8592(3)
_cell_length_c                   8.4098(3)
_cell_measurement_reflns_used    2961
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1241.90(6)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 1994)'
_computing_publication_material
;
SHELX97-2 (Sheldrick, 1997) and local procedures
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 18
_diffrn_measured_fraction_theta_full .999
_diffrn_measured_fraction_theta_max .999
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5547
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.91
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_T_max  0.9656
_exptl_absorpt_correction_T_min  0.9382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         .488
_refine_diff_density_min         -.393
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2841
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0658P)²+0.1233P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1176
_reflns_number_gt                2097
_reflns_number_total             2841
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2118.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2210152
_cod_database_fobs_code          2210152
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 0.08132(4) 0.41415(3) 0.88324(5) 0.02684(16) Uani d . 1
C C1 0.47419(14) 0.33014(11) 0.74240(19) 0.0175(4) Uani d . 1
C C1' 0.60066(15) 0.29805(12) 0.69207(18) 0.0175(4) Uani d . 1
C C2' 0.68983(14) 0.36276(12) 0.63629(18) 0.0166(4) Uani d . 1
C C2 0.41610(15) 0.28512(12) 0.86933(19) 0.0197(4) Uani d . 1
H H2 0.4601 0.2363 0.9270 0.024 Uiso calc R 1
C C3' 0.80447(15) 0.32948(12) 0.57751(19) 0.0190(4) Uani d . 1
C C3 0.29605(15) 0.30963(12) 0.91343(19) 0.0214(4) Uani d . 1
H H3 0.2580 0.2784 1.0006 0.026 Uiso calc R 1
C C4 0.23219(14) 0.38050(13) 0.8284(2) 0.0191(4) Uani d . 1
C C4' 0.83081(15) 0.23188(13) 0.5771(2) 0.0230(4) Uani d . 1
H H4' 0.9079 0.2090 0.5368 0.028 Uiso calc R 1
C C5 0.28610(15) 0.42613(12) 0.70002(19) 0.0185(4) Uani d . 1
H H5 0.2409 0.4740 0.6416 0.022 Uiso calc R 1
C C5' 0.74369(16) 0.16743(13) 0.6363(2) 0.0236(4) Uani d . 1
H H5' 0.7625 0.1004 0.6382 0.028 Uiso calc R 1
C C6 0.40670(15) 0.40098(12) 0.65821(19) 0.0172(4) Uani d . 1
H H6 0.4443 0.4324 0.5709 0.021 Uiso calc R 1
C C6' 0.63028(15) 0.19911(12) 0.6925(2) 0.0213(4) Uani d . 1
H H6' 0.5717 0.1538 0.7317 0.026 Uiso calc R 1
O O1' 0.66675(10) 0.46090(8) 0.63197(13) 0.0190(3) Uani d . 1
C C7' 0.70634(18) 0.50970(14) 0.7740(2) 0.0312(5) Uani d . 1
H H7A' 0.6574 0.4863 0.8635 0.047 Uiso calc R 1
H H7B' 0.6931 0.5793 0.7610 0.047 Uiso calc R 1
H H7C' 0.7956 0.4970 0.7951 0.047 Uiso calc R 1
O O2' 0.88284(10) 0.39978(8) 0.52168(14) 0.0220(3) Uani d . 1
C C8' 0.99806(16) 0.36793(14) 0.4557(2) 0.0277(4) Uani d . 1
H H8A' 1.0483 0.3345 0.5377 0.042 Uiso calc R 1
H H8B' 1.0448 0.4238 0.4170 0.042 Uiso calc R 1
H H8C' 0.9801 0.3237 0.3671 0.042 Uiso calc R 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl .1484 .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 118.00(15)
C2 C1 C1' 120.28(15)
C6 C1 C1' 121.58(14)
C2' C1' C6' 118.21(15)
C2' C1' C1 122.07(15)
C6' C1' C1 119.64(15)
O1' C2' C1' 121.26(14)
O1' C2' C3' 117.97(14)
C1' C2' C3' 120.74(15)
C3 C2 C1 121.68(15)
C3 C2 H2 119.2
C1 C2 H2 119.2
O2' C3' C4' 124.67(15)
O2' C3' C2' 115.32(14)
C4' C3' C2' 120.01(15)
C2 C3 C4 118.88(15)
C2 C3 H3 120.6
C4 C3 H3 120.6
C3 C4 C5 121.20(15)
C3 C4 Cl1 119.88(13)
C5 C4 Cl1 118.93(13)
C3' C4' C5' 119.43(16)
C3' C4' H4' 120.3
C5' C4' H4' 120.3
C6 C5 C4 119.08(16)
C6 C5 H5 120.5
C4 C5 H5 120.5
C6' C5' C4' 121.07(16)
C6' C5' H5' 119.5
C4' C5' H5' 119.5
C5 C6 C1 121.16(15)
C5 C6 H6 119.4
C1 C6 H6 119.4
C5' C6' C1' 120.51(16)
C5' C6' H6' 119.7
C1' C6' H6' 119.7
C2' O1' C7' 113.25(12)
O1' C7' H7A' 109.5
O1' C7' H7B' 109.5
H7A' C7' H7B' 109.5
O1' C7' H7C' 109.5
H7A' C7' H7C' 109.5
H7B' C7' H7C' 109.5
C3' O2' C8' 116.65(13)
O2' C8' H8A' 109.5
O2' C8' H8B' 109.5
H8A' C8' H8B' 109.5
O2' 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 C4 1.7460(16)
C1 C2 1.393(2)
C1 C6 1.400(2)
C1 C1' 1.490(2)
C1' C2' 1.395(2)
C1' C6' 1.407(2)
C2' O1' 1.3826(19)
C2' C3' 1.406(2)
C2 C3 1.382(2)
C2 H2 0.95
C3' O2' 1.3729(19)
C3' C4' 1.382(2)
C3 C4 1.385(2)
C3 H3 0.95
C4 C5 1.387(2)
C4' C5' 1.389(2)
C4' H4' 0.95
C5 C6 1.385(2)
C5 H5 0.95
C5' C6' 1.379(2)
C5' H5' 0.95
C6 H6 0.95
C6' H6' 0.95
O1' C7' 1.4285(19)
C7' H7A' 0.98
C7' H7B' 0.98
C7' H7C' 0.98
O2' C8' 1.429(2)
C8' H8A' 0.98
C8' H8B' 0.98
C8' H8C' 0.98
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
C5 H5 O2' 3_666 0.95 2.57 3.520(2) 179
C6 H6 O1' . 0.95 2.45 2.906(2) 110
C6 H6 O1' 3_666 0.95 2.53 3.185(2) 126
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
C2 C1 C1' C2' -144.42(16)
C6 C1 C1' C2' 40.1(2)
C2 C1 C1' C6' 38.9(2)
C6 C1 C1' C6' -136.64(16)
C6' C1' C2' O1' 179.73(13)
C1 C1' C2' O1' 3.0(2)
C6' C1' C2' C3' 2.0(2)
C1 C1' C2' C3' -174.77(14)
C6 C1 C2 C3 -0.7(2)
C1' C1 C2 C3 -176.43(15)
O1' C2' C3' O2' 0.3(2)
C1' C2' C3' O2' 178.12(14)
O1' C2' C3' C4' -179.00(14)
C1' C2' C3' C4' -1.2(2)
C1 C2 C3 C4 0.3(3)
C2 C3 C4 C5 0.6(3)
C2 C3 C4 Cl1 -179.08(13)
O2' C3' C4' C5' -179.71(15)
C2' C3' C4' C5' -0.5(2)
C3 C4 C5 C6 -1.0(3)
Cl1 C4 C5 C6 178.72(12)
C3' C4' C5' C6' 1.3(3)
C4 C5 C6 C1 0.5(2)
C2 C1 C6 C5 0.4(2)
C1' C1 C6 C5 175.99(15)
C4' C5' C6' C1' -0.5(3)
C2' C1' C6' C5' -1.2(2)
C1 C1' C6' C5' 175.66(14)
C1' C2' O1' C7' 90.65(18)
C3' C2' O1' C7' -91.52(17)
C4' C3' O2' C8' 1.5(2)
C2' C3' O2' C8' -177.73(14)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21127575
