#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/68/4506877.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_4506877
loop_
_publ_author_name
'Nath, Naba K.'
'Nangia, Ashwini'
_publ_section_title
;
 Isomorphous Crystals by Chloro--Methyl Exchange in Polymorphic Fuchsones
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5411
_journal_paper_doi               10.1021/cg3010097
_journal_volume                  12
_journal_year                    2012
_chemical_formula_sum            'C21.5 H17.75 Cl1.5 O'
_chemical_formula_weight         345.28
_chemical_name_systematic
; 
 ? 
;
_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   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                   19.853(3)
_cell_length_b                   10.8323(15)
_cell_length_c                   7.8131(11)
_cell_measurement_reflns_used    4194
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.14
_cell_volume                     1680.2(4)
_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      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0460
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7930
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.311
_exptl_absorpt_correction_T_max  0.9519
_exptl_absorpt_correction_T_min  0.8882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             721
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.319
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1500
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.319
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0579
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0176P)²+4.4644P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1179
_reflns_number_gt                1402
_reflns_number_total             1500
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg3010097_si_013.cif
_cod_data_source_block           TMF+MCF-3
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        1680.3(4)
_cod_original_sg_symbol_H-M      'C2/c  '
_cod_original_formula_sum        'C21.50 H17.75 Cl1.50 O'
_cod_database_code               4506877
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_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
C13 C 0.24906(5) 0.19450(9) 0.22479(13) 0.0296(4) Uani 0.287(6) 1 d P A 1
H13A H 0.2490 0.1417 0.1230 0.044 Uiso 0.287(6) 1 calc PR A 1
H13B H 0.2088 0.2470 0.2240 0.044 Uiso 0.287(6) 1 calc PR A 1
H13C H 0.2489 0.1429 0.3278 0.044 Uiso 0.287(6) 1 calc PR A 1
Cl1 Cl 0.24906(5) 0.19450(9) 0.22479(13) 0.0296(4) Uani 0.713(6) 1 d P A 1
C3 C 0.44341(13) 0.7009(3) 0.1858(3) 0.0199(6) Uani 1 1 d . . .
H3 H 0.4048 0.6577 0.1460 0.024 Uiso 1 1 calc R . .
C5 C 0.5000 0.5015(4) 0.2500 0.0201(9) Uani 1 2 d S . .
C6 C 0.43679(13) 0.4288(2) 0.2381(3) 0.0177(6) Uani 1 1 d . A .
C7 C 0.37760(13) 0.4673(3) 0.3206(3) 0.0195(6) Uani 1 1 d . . .
H7 H 0.3773 0.5432 0.3817 0.023 Uiso 1 1 calc R . .
C8 C 0.31963(13) 0.3965(3) 0.3144(4) 0.0222(6) Uani 1 1 d . A .
H8 H 0.2800 0.4233 0.3714 0.027 Uiso 1 1 calc R . .
C2 C 0.44297(13) 0.8250(3) 0.1798(3) 0.0214(6) Uani 1 1 d . . .
C9 C 0.31986(14) 0.2857(3) 0.2240(4) 0.0228(7) Uani 1 1 d . . .
O1 O 0.5000 1.0100(3) 0.2500 0.0317(7) Uani 1 2 d S . .
C4 C 0.5000 0.6298(3) 0.2500 0.0171(8) Uani 1 2 d S . .
C12 C 0.38713(14) 0.8972(3) 0.0990(4) 0.0262(7) Uani 1 1 d . . .
H12A H 0.3530 0.8402 0.0545 0.039 Uiso 1 1 calc R . .
H12B H 0.4052 0.9470 0.0048 0.039 Uiso 1 1 calc R . .
H12C H 0.3666 0.9515 0.1846 0.039 Uiso 1 1 calc R . .
C11 C 0.43545(13) 0.3170(3) 0.1494(3) 0.0199(6) Uani 1 1 d . . .
H11 H 0.4751 0.2888 0.0937 0.024 Uiso 1 1 calc R A .
C10 C 0.37746(14) 0.2466(3) 0.1411(4) 0.0229(6) Uani 1 1 d . A .
H10 H 0.3772 0.1714 0.0785 0.027 Uiso 1 1 calc R . .
C1 C 0.5000 0.8958(4) 0.2500 0.0208(9) Uani 1 2 d S . .
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'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C9 C13 H13A 109.5 . .
C9 C13 H13B 109.5 . .
C9 C13 H13C 109.5 . .
C2 C3 C4 123.2(3) . .
C2 C3 H3 118.4 . .
C4 C3 H3 118.4 . .
C4 C5 C6 122.05(17) . .
C4 C5 C6 122.05(17) . 2_655
C6 C5 C6 115.9(3) . 2_655
C11 C6 C7 118.0(2) . .
C11 C6 C5 120.5(2) . .
C7 C6 C5 121.4(2) . .
C8 C7 C6 121.0(3) . .
C8 C7 H7 119.5 . .
C6 C7 H7 119.5 . .
C7 C8 C9 119.5(3) . .
C7 C8 H8 120.2 . .
C9 C8 H8 120.2 . .
C3 C2 C1 120.1(3) . .
C3 C2 C12 122.8(3) . .
C1 C2 C12 117.1(2) . .
C10 C9 C8 120.3(3) . .
C10 C9 C13 120.2(2) . .
C8 C9 C13 119.4(2) . .
C5 C4 C3 122.05(17) . .
C5 C4 C3 122.05(17) . 2_655
C3 C4 C3 115.9(3) . 2_655
C2 C12 H12A 109.5 . .
C2 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C2 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C10 C11 C6 121.2(3) . .
C10 C11 H11 119.4 . .
C6 C11 H11 119.4 . .
C9 C10 C11 119.9(3) . .
C9 C10 H10 120.0 . .
C11 C10 H10 120.0 . .
O1 C1 C2 121.34(17) . 2_655
O1 C1 C2 121.34(17) . .
C2 C1 C2 117.3(3) 2_655 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C13 C9 1.718(3) .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C3 C2 1.345(4) .
C3 C4 1.452(3) .
C3 H3 0.9500 .
C5 C4 1.390(5) .
C5 C6 1.485(3) .
C5 C6 1.485(3) 2_655
C6 C11 1.396(4) .
C6 C7 1.404(4) .
C7 C8 1.384(4) .
C7 H7 0.9500 .
C8 C9 1.393(4) .
C8 H8 0.9500 .
C2 C1 1.473(3) .
C2 C12 1.496(4) .
C9 C10 1.381(4) .
O1 C1 1.238(5) .
C4 C3 1.452(3) 2_655
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C11 C10 1.382(4) .
C11 H11 0.9500 .
C10 H10 0.9500 .
C1 C2 1.473(3) 2_655
