#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/82/2238221.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_2238221
loop_
_publ_author_name
'Sanders, Marisa B.'
'Leon, David'
'Ndichie, Eddy I.'
'Chan, Benny C.'
_publ_section_title
;
 1,3-Bis(chloromethyl)benzene
;
_journal_coeditor_code           MW2106
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1150
_journal_paper_doi               10.1107/S1600536813016383
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C8 H8 Cl2'
_chemical_formula_moiety         'C8 H8 Cl2'
_chemical_formula_sum            'C8 H8 Cl2'
_chemical_formula_weight         175.04
_chemical_name_common            'm-Xylylene dichloride'
_chemical_name_systematic
;
1,3-Bis(chloromethyl)benzene
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'APEX2 v2011.1-2'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.5174(5)
_cell_length_b                   12.3094(7)
_cell_length_c                   15.2597(9)
_cell_measurement_reflns_used    120
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      28.2270
_cell_measurement_theta_min      2.6900
_cell_volume                     1599.89(16)
_computing_cell_refinement       'SAINT (Bruker, 2011)'
_computing_data_collection       'APEX2 (Bruker, 2011)'
_computing_data_reduction        'SAINT (Bruker, 2011)'
_computing_molecular_graphics    'CrystalMaker (CrystalMaker Software, 2009)'
_computing_publication_material  'enCIFer (Allen et al. 2004)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0142
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17126
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.63
_diffrn_reflns_theta_min         2.67
_exptl_absorpt_coefficient_mu    0.727
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2011)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thick plate'
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.235
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1949
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0232
_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)+(0.0356P)²+0.6168P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0623
_refine_ls_wR_factor_ref         0.0644
_reflns_number_gt                1782
_reflns_number_total             1949
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            mw2106.cif
_cod_data_source_block           I
_cod_database_code               2238221
_cod_database_fobs_code          2238221
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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
_atom_site_symmetry_multiplicity
Cl Cl1 0.61622(3) 0.35365(2) 1.030229(18) 0.02078(9) Uani d . 1 1
Cl Cl2 0.83843(3) 0.32450(2) 0.660472(18) 0.02164(10) Uani d . 1 1
C C1 0.81471(14) 0.40672(11) 1.02366(8) 0.0210(3) Uani d . 1 1
H H1A 0.8343 0.4563 1.0736 0.025 Uiso calc R 1 1
H H1B 0.8909 0.3462 1.0272 0.025 Uiso calc R 1 1
C C2 0.83655(13) 0.46689(10) 0.93903(7) 0.0159(2) Uani d . 1 1
C C3 0.90389(13) 0.41528(9) 0.86690(8) 0.0161(2) Uani d . 1 1
H H3 0.9394 0.3424 0.8722 0.019 Uiso calc R 1 1
C C4 0.91971(13) 0.46956(9) 0.78693(7) 0.0165(2) Uani d . 1 1
C C5 0.98635(14) 0.41163(11) 0.70880(8) 0.0218(3) Uani d . 1 1
H H5A 1.0779 0.3675 0.7269 0.026 Uiso calc R 1 1
H H5B 1.0224 0.4654 0.6650 0.026 Uiso calc R 1 1
C C6 0.78830(13) 0.57490(10) 0.93140(8) 0.0182(2) Uani d . 1 1
H H6 0.7434 0.6110 0.9804 0.022 Uiso calc R 1 1
C C7 0.80570(15) 0.62972(10) 0.85252(8) 0.0209(2) Uani d . 1 1
H H7 0.7736 0.7034 0.8478 0.025 Uiso calc R 1 1
C C8 0.87016(14) 0.57693(10) 0.78021(8) 0.0196(2) Uani d . 1 1
H H8 0.8803 0.6144 0.7261 0.024 Uiso calc R 1 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 0.01567(15) 0.02646(17) 0.02020(16) -0.00530(11) 0.00008(10) 0.00373(11)
Cl2 0.02070(16) 0.02609(17) 0.01814(15) -0.00366(11) 0.00164(10) -0.00641(11)
C1 0.0148(5) 0.0300(7) 0.0181(6) -0.0067(5) -0.0028(4) 0.0046(5)
C2 0.0113(5) 0.0219(6) 0.0145(5) -0.0039(4) -0.0025(4) 0.0009(4)
C3 0.0121(5) 0.0165(5) 0.0196(6) -0.0015(4) -0.0019(4) 0.0000(4)
C4 0.0117(5) 0.0216(6) 0.0162(5) -0.0028(4) -0.0004(4) -0.0022(4)
C5 0.0150(5) 0.0298(7) 0.0206(6) -0.0035(5) 0.0013(4) -0.0065(5)
C6 0.0158(5) 0.0216(6) 0.0173(5) -0.0008(4) 0.0018(4) -0.0041(4)
C7 0.0209(6) 0.0166(6) 0.0250(6) 0.0013(4) 0.0000(5) 0.0012(5)
C8 0.0192(5) 0.0227(6) 0.0171(5) -0.0017(5) 0.0000(4) 0.0039(5)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 Cl1 109.92(8)
C2 C1 H1A 109.7
Cl1 C1 H1A 109.7
C2 C1 H1B 109.7
Cl1 C1 H1B 109.7
H1A C1 H1B 108.2
C3 C2 C6 119.28(11)
C3 C2 C1 120.37(11)
C6 C2 C1 120.35(11)
C2 C3 C4 120.73(11)
C2 C3 H3 119.6
C4 C3 H3 119.6
C8 C4 C3 119.29(11)
C8 C4 C5 120.50(11)
C3 C4 C5 120.19(11)
C4 C5 Cl2 109.97(8)
C4 C5 H5A 109.7
Cl2 C5 H5A 109.7
C4 C5 H5B 109.7
Cl2 C5 H5B 109.7
H5A C5 H5B 108.2
C7 C6 C2 120.25(11)
C7 C6 H6 119.9
C2 C6 H6 119.9
C6 C7 C8 120.14(11)
C6 C7 H7 119.9
C8 C7 H7 119.9
C4 C8 C7 120.28(11)
C4 C8 H8 119.9
C7 C8 H8 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.8152(12)
Cl2 C5 1.8115(12)
C1 C2 1.5004(16)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.3944(16)
C2 C6 1.3964(17)
C3 C4 1.3978(16)
C3 H3 0.9500
C4 C8 1.3912(17)
C4 C5 1.5007(16)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.3879(17)
C6 H6 0.9500
C7 C8 1.3933(17)
C7 H7 0.9500
C8 H8 0.9500
