#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/38/2013858.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_2013858
loop_
_publ_author_name
'Turowska-Tyrk, Ilona'
'Grześniak, Karolina'
_publ_section_title
;
 Monitoring structural transformations in crystals. 7.
 1-Chloroanthracene and its photodimer
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o146
_journal_page_last               o148
_journal_paper_doi               10.1107/S0108270103026775
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C28 H18 Cl2'
_chemical_formula_moiety         'C28 H18 Cl2'
_chemical_formula_sum            'C28 H18 Cl2'
_chemical_formula_weight         425.32
_chemical_name_common            '1-chloroanthracene photodimer'
_chemical_name_systematic
;
trans-bi(1-chloro-9,10-dihydro-9,10-anthracenediyl)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 101.475(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.232(2)
_cell_length_b                   11.0746(13)
_cell_length_c                   9.0872(11)
_cell_measurement_reflns_used    1164
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22
_cell_measurement_theta_min      5
_cell_volume                     1995.4(4)
_computing_cell_refinement       'KM-4 CCD Software'
_computing_data_collection       'KM-4 CCD Software (Kuma Diffraction, 2000)'
_computing_data_reduction        'KM-4 CCD Software'
_computing_molecular_graphics    'ORTEP-3 (Johnson et al., 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Kuma KM-4 CCD area-detector'
_diffrn_measurement_method       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  0.030
_diffrn_reflns_av_sigmaI/netI    0.034
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4922
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         5.88
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.339
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         1945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.061
_refine_ls_R_factor_gt           0.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.06P)²+0.9967P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.109
_refine_ls_wR_factor_ref         0.119
_reflns_number_gt                1545
_reflns_number_total             1945
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk1681.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2013858
_cod_database_fobs_code          2013858
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x, y, -z-1/2'
'-x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z-1/2'
loop_
_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cl1 0.05591(3) 0.79196(6) 0.11803(7) 0.0544(2) Uani d . 1 . . Cl
C1 0.09676(10) 0.6850(2) 0.0283(2) 0.0360(5) Uani d . 1 . . C
C2 0.05764(12) 0.5988(2) -0.0591(3) 0.0445(6) Uani d . 1 . . C
C3 0.08870(12) 0.5126(2) -0.1304(3) 0.0462(6) Uani d . 1 . . C
C4 0.15778(12) 0.5135(2) -0.1175(2) 0.0394(5) Uani d . 1 . . C
C5 0.36415(11) 0.5823(2) 0.2106(3) 0.0417(5) Uani d . 1 . . C
C6 0.39430(13) 0.6158(2) 0.3550(3) 0.0501(6) Uani d . 1 . . C
C7 0.36493(13) 0.7020(2) 0.4295(3) 0.0486(6) Uani d . 1 . . C
C8 0.30482(11) 0.7551(2) 0.3610(2) 0.0404(5) Uani d . 1 . . C
C9 0.21126(10) 0.78342(18) 0.1312(2) 0.0318(5) Uani d . 1 . . C
C10 0.27151(10) 0.61173(19) -0.0212(2) 0.0321(5) Uani d . 1 . . C
C11 0.16630(10) 0.68827(18) 0.0444(2) 0.0319(5) Uani d . 1 . . C
C12 0.19651(10) 0.60097(18) -0.0316(2) 0.0324(5) Uani d . 1 . . C
C13 0.30484(10) 0.63614(18) 0.1398(2) 0.0331(5) Uani d . 1 . . C
C14 0.27477(10) 0.72307(18) 0.2160(2) 0.0330(5) Uani d . 1 . . C
H2 0.0091(14) 0.600(2) -0.070(3) 0.056(7) Uiso d . 1 . . H
H3 0.0605(15) 0.451(3) -0.186(3) 0.066(8) Uiso d . 1 . . H
H4 0.1779(10) 0.455(2) -0.169(2) 0.031(5) Uiso d . 1 . . H
H5 0.3863(12) 0.525(2) 0.157(3) 0.043(6) Uiso d . 1 . . H
H6 0.4353(14) 0.580(2) 0.399(3) 0.057(7) Uiso d . 1 . . H
H7 0.3871(14) 0.723(2) 0.532(3) 0.061(8) Uiso d . 1 . . H
H8 0.2850(13) 0.814(2) 0.414(3) 0.048(7) Uiso d . 1 . . H
H9 0.1903(11) 0.822(2) 0.200(3) 0.035(6) Uiso d . 1 . . H
H10 0.2890(11) 0.538(2) -0.054(3) 0.042(6) Uiso d . 1 . . H
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C11 . . 122.0(2) no
C2 C1 Cl1 . . 117.93(17) no
C11 C1 Cl1 . . 120.03(16) no
C3 C2 C1 . . 119.1(2) no
C3 C2 H2 . . 120.6(16) no
C1 C2 H2 . . 120.2(16) no
C2 C3 C4 . . 120.4(2) no
C2 C3 H3 . . 117.3(17) no
C4 C3 H3 . . 122.3(17) no
C3 C4 C12 . . 120.2(2) no
C3 C4 H4 . . 119.0(13) no
C12 C4 H4 . . 120.7(13) no
C13 C5 C6 . . 120.3(2) no
C13 C5 H5 . . 119.8(14) no
C6 C5 H5 . . 119.7(14) no
C7 C6 C5 . . 120.2(2) no
C7 C6 H6 . . 121.3(16) no
C5 C6 H6 . . 118.5(16) no
C6 C7 C8 . . 120.1(2) no
C6 C7 H7 . . 118.4(16) no
C8 C7 H7 . . 121.4(16) no
C7 C8 C14 . . 120.0(2) no
C7 C8 H8 . . 119.2(15) no
C14 C8 H8 . . 120.7(15) no
C11 C9 C14 . . 108.66(17) no
C11 C9 C10 . 7_565 111.13(16) no
C14 C9 C10 . 7_565 111.49(16) no
C11 C9 H9 . . 111.4(14) no
C14 C9 H9 . . 108.3(14) no
C10 C9 H9 7_565 . 105.8(14) no
C12 C10 C13 . . 109.02(16) no
C12 C10 C9 . 7_565 110.89(16) no
C13 C10 C9 . 7_565 111.20(16) no
C12 C10 H10 . . 110.0(14) no
C13 C10 H10 . . 109.5(14) no
C9 C10 H10 7_565 . 106.1(14) no
C1 C11 C12 . . 117.68(18) no
C1 C11 C9 . . 124.56(19) no
C12 C11 C9 . . 117.66(17) no
C4 C12 C11 . . 120.54(19) no
C4 C12 C10 . . 122.76(19) no
C11 C12 C10 . . 116.63(17) no
C5 C13 C14 . . 119.48(19) no
C5 C13 C10 . . 123.67(19) no
C14 C13 C10 . . 116.76(18) no
C8 C14 C13 . . 119.8(2) no
C8 C14 C9 . . 122.6(2) no
C13 C14 C9 . . 117.48(17) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 . 1.737(2) no
C1 C2 . 1.385(3) no
C1 C11 . 1.386(3) no
C2 C3 . 1.374(4) no
C2 H2 . 0.97(3) no
C3 C4 . 1.379(3) no
C3 H3 . 0.96(3) no
C4 C12 . 1.385(3) no
C4 H4 . 0.94(2) no
C5 C13 . 1.379(3) no
C5 C6 . 1.383(3) no
C5 H5 . 0.96(2) no
C6 C7 . 1.372(4) no
C6 H6 . 0.94(3) no
C7 C8 . 1.382(3) no
C7 H7 . 0.98(3) no
C8 C14 . 1.383(3) no
C8 H8 . 0.95(3) no
C9 C11 . 1.508(3) yes
C9 C14 . 1.516(3) yes
C9 C10 7_565 1.615(3) yes
C9 H9 . 0.92(2) no
C10 C12 . 1.506(3) yes
C10 C13 . 1.508(3) yes
C10 C9 7_565 1.615(3) no
C10 H10 . 0.96(2) no
C11 C12 . 1.398(3) yes
C13 C14 . 1.394(3) yes
