#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/68/4506869.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_4506869
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            'C24.5 H16 Cl2 O'
_chemical_formula_weight         397.27
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.2630(10)
_cell_angle_beta                 103.8560(10)
_cell_angle_gamma                91.1900(10)
_cell_formula_units_Z            2
_cell_length_a                   7.2779(7)
_cell_length_b                   11.8390(11)
_cell_length_c                   12.4604(11)
_cell_measurement_reflns_used    6259
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.02
_cell_measurement_theta_min      2.70
_cell_volume                     1019.73(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10683
_diffrn_reflns_theta_full        26.08
_diffrn_reflns_theta_max         26.08
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_T_max  0.9584
_exptl_absorpt_correction_T_min  0.9019
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             410
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4000
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0396
_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)+(0.0679P)²+0.3020P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1138
_reflns_number_gt                3422
_reflns_number_total             4000
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg3010097_si_005.cif
_cod_data_source_block           CMF-t
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed
to 'constr' 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_sg_symbol_H-M      'P-1   '
_cod_original_formula_sum        'C24.50 H16 Cl2 O'
_cod_database_code               4506869
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C1 C 0.2099(2) -0.07672(14) 0.01731(15) 0.0198(4) Uani 1 1 d .
C2 C 0.2669(2) 0.02674(15) -0.01807(14) 0.0183(4) Uani 1 1 d .
C3 C 0.2998(2) 0.13190(15) 0.04960(14) 0.0183(4) Uani 1 1 d .
H3 H 0.3401 0.1951 0.0221 0.022 Uiso 1 1 calc R
C4 C 0.2755(2) 0.15138(15) 0.16351(14) 0.0176(4) Uani 1 1 d .
C5 C 0.2177(2) 0.05152(15) 0.20140(15) 0.0195(4) Uani 1 1 d .
H5 H 0.1991 0.0606 0.2754 0.023 Uiso 1 1 calc R
C6 C 0.1897(2) -0.05366(15) 0.13401(15) 0.0199(4) Uani 1 1 d .
C7 C 0.3009(2) 0.26107(15) 0.23079(14) 0.0186(4) Uani 1 1 d .
C8 C 0.4042(3) 0.35600(14) 0.20389(14) 0.0191(4) Uani 1 1 d .
C9 C 0.5762(3) 0.33977(15) 0.17420(14) 0.0216(4) Uani 1 1 d .
H9 H 0.6288 0.2668 0.1722 0.026 Uiso 1 1 calc R
C10 C 0.6713(3) 0.42911(17) 0.14751(15) 0.0280(4) Uani 1 1 d .
H10 H 0.7888 0.4166 0.1281 0.034 Uiso 1 1 calc R
C11 C 0.5975(3) 0.53633(17) 0.14870(16) 0.0325(5) Uani 1 1 d .
C12 C 0.4267(3) 0.55270(16) 0.17873(16) 0.0328(5) Uani 1 1 d .
H12 H 0.3742 0.6256 0.1798 0.039 Uiso 1 1 calc R
C13 C 0.3311(3) 0.46477(15) 0.20720(15) 0.0259(4) Uani 1 1 d .
H13 H 0.2157 0.4784 0.2290 0.031 Uiso 1 1 calc R
C14 C 0.2184(2) 0.29027(14) 0.32931(14) 0.0189(4) Uani 1 1 d .
C15 C 0.0306(3) 0.25378(15) 0.32050(15) 0.0218(4) Uani 1 1 d .
H15 H -0.0421 0.2069 0.2520 0.026 Uiso 1 1 calc R
C16 C -0.0507(3) 0.28562(16) 0.41118(15) 0.0231(4) Uani 1 1 d .
H16 H -0.1789 0.2606 0.4036 0.028 Uiso 1 1 calc R
C17 C 0.0517(3) 0.35305(16) 0.51234(15) 0.0226(4) Uani 1 1 d .
C18 C 0.2383(3) 0.39028(16) 0.52130(15) 0.0259(4) Uani 1 1 d .
H18 H 0.3102 0.4366 0.5903 0.031 Uiso 1 1 calc R
C19 C 0.3215(3) 0.36087(16) 0.43111(15) 0.0235(4) Uani 1 1 d .
H19 H 0.4483 0.3885 0.4383 0.028 Uiso 1 1 calc R
C20 C 0.6991(4) 0.6323(2) 0.11635(19) 0.0515(7) Uani 1 1 d .
H20A H 0.6446 0.6338 0.0367 0.077 Uiso 1 1 calc R
H20B H 0.8342 0.6189 0.1278 0.077 Uiso 1 1 calc R
H20C H 0.6844 0.7065 0.1636 0.077 Uiso 1 1 calc R
C21 C -0.0371(3) 0.38478(18) 0.61084(16) 0.0297(4) Uani 1 1 d .
H21A H -0.1749 0.3853 0.5827 0.045 Uiso 1 1 calc R
H21B H 0.0146 0.4616 0.6546 0.045 Uiso 1 1 calc R
H21C H -0.0088 0.3281 0.6592 0.045 Uiso 1 1 calc R
Cl1 Cl 0.28966(6) 0.00779(4) -0.15582(3) 0.02206(14) Uani 1 1 d .
Cl2 Cl 0.12568(7) -0.17354(4) 0.18077(4) 0.02730(15) Uani 1 1 d .
O1 O 0.18053(19) -0.17286(10) -0.04463(11) 0.0263(3) Uani 1 1 d .
C29 C 0.707(2) 0.9111(15) 0.4146(18) 0.142(12) Uani 0.50 1 d PD
C24 C 0.621(2) 1.0919(13) 0.5262(10) 0.098(7) Uani 0.50 1 d PD
C23 C 0.5617(10) 0.9696(6) 0.4741(4) 0.0652(18) Uani 0.50 1 d PD
C28 C 0.4022(13) 0.9182(8) 0.4774(9) 0.052(4) Uani 0.50 1 d PD
C26 C 0.311(2) 1.0928(16) 0.5789(16) 0.086(6) Uani 0.50 1 d PD
C25 C 0.4745(14) 1.1411(6) 0.5782(6) 0.084(3) Uani 0.50 1 d PD
C27 C 0.2656(12) 0.9801(10) 0.5368(9) 0.098(3) Uani 0.50 1 d PD
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
O1 C1 C2 123.32(16) . .
O1 C1 C6 123.41(16) . .
C2 C1 C6 113.28(14) . .
C3 C2 C1 123.46(15) . .
C3 C2 Cl1 120.19(13) . .
C1 C2 Cl1 116.35(12) . .
C2 C3 C4 121.57(16) . .
C2 C3 H3 119.2 . .
C4 C3 H3 119.2 . .
C7 C4 C5 122.14(16) . .
C7 C4 C3 121.15(15) . .
C5 C4 C3 116.68(15) . .
C6 C5 C4 121.23(16) . .
C6 C5 H5 119.4 . .
C4 C5 H5 119.4 . .
C5 C6 C1 123.75(16) . .
C5 C6 Cl2 121.10(14) . .
C1 C6 Cl2 115.15(13) . .
C4 C7 C8 121.24(15) . .
C4 C7 C14 121.89(15) . .
C8 C7 C14 116.80(14) . .
C9 C8 C13 118.42(16) . .
C9 C8 C7 120.99(16) . .
C13 C8 C7 120.59(16) . .
C10 C9 C8 120.63(18) . .
C10 C9 H9 119.7 . .
C8 C9 H9 119.7 . .
C11 C10 C9 121.08(19) . .
C11 C10 H10 119.5 . .
C9 C10 H10 119.5 . .
C10 C11 C12 118.31(17) . .
C10 C11 C20 120.8(2) . .
C12 C11 C20 120.9(2) . .
C13 C12 C11 121.35(19) . .
C13 C12 H12 119.3 . .
C11 C12 H12 119.3 . .
C12 C13 C8 120.18(19) . .
C12 C13 H13 119.9 . .
C8 C13 H13 119.9 . .
C15 C14 C19 118.47(16) . .
C15 C14 C7 120.20(15) . .
C19 C14 C7 121.21(16) . .
C16 C15 C14 120.48(16) . .
C16 C15 H15 119.8 . .
C14 C15 H15 119.8 . .
C17 C16 C15 121.20(17) . .
C17 C16 H16 119.4 . .
C15 C16 H16 119.4 . .
C16 C17 C18 118.55(16) . .
C16 C17 C21 120.61(17) . .
C18 C17 C21 120.84(17) . .
C19 C18 C17 121.20(17) . .
C19 C18 H18 119.4 . .
C17 C18 H18 119.4 . .
C18 C19 C14 120.08(17) . .
C18 C19 H19 120.0 . .
C14 C19 H19 120.0 . .
C11 C20 H20A 109.5 . .
C11 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C11 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C17 C21 H21A 109.5 . .
C17 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C17 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C26 C29 C27 98(10) 2_676 2_676
C26 C29 C25 22(10) 2_676 2_676
C27 C29 C25 112.3(8) 2_676 2_676
C26 C29 C23 41(10) 2_676 .
C27 C29 C23 59.7(6) 2_676 .
C25 C29 C23 52.6(5) 2_676 .
C28 C24 C25 65(6) 2_676 .
C28 C24 C27 101(7) 2_676 2_676
C25 C24 C27 166.4(15) . 2_676
C28 C24 C23 44(6) 2_676 .
C25 C24 C23 108.2(13) . .
C27 C24 C23 58.4(7) 2_676 .
C28 C24 C23 14(6) 2_676 2_676
C25 C24 C23 53.6(7) . 2_676
C27 C24 C23 112.9(12) 2_676 2_676
C23 C24 C23 54.6(8) . 2_676
C28 C23 C28 118.0(6) . 2_676
C28 C23 C25 63.0(8) . 2_676
C28 C23 C25 177.8(8) 2_676 2_676
C28 C23 C23 60.0(7) . 2_676
C28 C23 C23 58.0(7) 2_676 2_676
C25 C23 C23 122.9(10) 2_676 2_676
C28 C23 C26 120.1(9) . 2_676
C28 C23 C26 121.9(11) 2_676 2_676
C25 C23 C26 57.2(10) 2_676 2_676
C23 C23 C26 179.8(15) 2_676 2_676
C28 C23 C27 176.0(8) . 2_676
C28 C23 C27 65.5(7) 2_676 2_676
C25 C23 C27 113.5(9) 2_676 2_676
C23 C23 C27 123.5(10) 2_676 2_676
C26 C23 C27 56.4(9) 2_676 2_676
C28 C23 C24 123.7(9) . .
C28 C23 C24 5.9(10) 2_676 .
C25 C23 C24 173.3(10) 2_676 .
C23 C23 C24 63.8(8) 2_676 .
C26 C23 C24 116.1(11) 2_676 .
C27 C23 C24 59.8(8) 2_676 .
C28 C23 C24 2.0(9) . 2_676
C28 C23 C24 119.7(10) 2_676 2_676
C25 C23 C24 61.2(7) 2_676 2_676
C23 C23 C24 61.7(8) 2_676 2_676
C26 C23 C24 118.4(13) 2_676 2_676
C27 C23 C24 174.0(9) 2_676 2_676
C24 C23 C24 125.4(8) . 2_676
C28 C23 C29 124.5(10) . .
C28 C23 C29 117.5(9) 2_676 .
C25 C23 C29 61.5(7) 2_676 .
C23 C23 C29 175.2(11) 2_676 .
C26 C23 C29 4.8(13) 2_676 .
C27 C23 C29 52.0(9) 2_676 .
C24 C23 C29 111.8(11) . .
C24 C23 C29 122.7(8) 2_676 .
C24 C28 C23 164(7) 2_676 .
C24 C28 C23 131(7) 2_676 2_676
C23 C28 C23 62.0(6) . 2_676
C24 C28 C25 107(7) 2_676 2_676
C23 C28 C25 59.3(6) . 2_676
C23 C28 C25 121.3(9) 2_676 2_676
C24 C28 C27 72(6) 2_676 .
C23 C28 C27 122.0(8) . .
C23 C28 C27 60.0(6) 2_676 .
C25 C28 C27 178.7(9) 2_676 .
C29 C26 C25 155(10) 2_676 .
C29 C26 C27 74(10) 2_676 .
C25 C26 C27 121.2(12) . .
C29 C26 C23 134(10) 2_676 2_676
C25 C26 C23 58.8(7) . 2_676
C27 C26 C23 62.7(9) . 2_676
C26 C25 C23 64.0(9) . 2_676
C26 C25 C28 121.7(8) . 2_676
C23 C25 C28 57.7(7) 2_676 2_676
C26 C25 C24 129.1(12) . .
C23 C25 C24 65.1(7) 2_676 .
C28 C25 C24 7.5(10) 2_676 .
C26 C25 C29 3.0(16) . 2_676
C23 C25 C29 65.9(7) 2_676 2_676
C28 C25 C29 123.6(10) 2_676 2_676
C24 C25 C29 131.0(9) . 2_676
C29 C27 C26 7.7(9) 2_676 .
C29 C27 C23 68.3(7) 2_676 2_676
C26 C27 C23 60.9(8) . 2_676
C29 C27 C24 130.1(12) 2_676 2_676
C26 C27 C24 122.6(11) . 2_676
C23 C27 C24 61.8(8) 2_676 2_676
C29 C27 C28 122.7(8) 2_676 .
C26 C27 C28 115.3(9) . .
C23 C27 C28 54.4(6) 2_676 .
C24 C27 C28 7.5(10) 2_676 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.227(2) .
C1 C2 1.464(2) .
C1 C6 1.469(2) .
C2 C3 1.341(2) .
C2 Cl1 1.7353(17) .
C3 C4 1.447(2) .
C3 H3 0.9500 .
C4 C7 1.384(2) .
C4 C5 1.446(2) .
C5 C6 1.340(2) .
C5 H5 0.9500 .
C6 Cl2 1.7312(17) .
C7 C8 1.474(2) .
C7 C14 1.478(2) .
C8 C9 1.394(3) .
C8 C13 1.401(2) .
C9 C10 1.388(3) .
C9 H9 0.9500 .
C10 C11 1.387(3) .
C10 H10 0.9500 .
C11 C12 1.388(3) .
C11 C20 1.513(3) .
C12 C13 1.388(3) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 C15 1.397(3) .
C14 C19 1.405(2) .
C15 C16 1.390(2) .
C15 H15 0.9500 .
C16 C17 1.383(3) .
C16 H16 0.9500 .
C17 C18 1.391(3) .
C17 C21 1.508(2) .
C18 C19 1.390(3) .
C18 H18 0.9500 .
C19 H19 0.9500 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C29 C26 0.18(2) 2_676
C29 C27 1.30(2) 2_676
C29 C25 1.477(17) 2_676
C29 C23 1.534(9) .
C24 C28 0.20(3) 2_676
C24 C25 1.453(17) .
C24 C27 1.448(16) 2_676
C24 C23 1.476(17) .
C24 C23 1.504(18) 2_676
C23 C28 1.312(13) .
C23 C28 1.339(13) 2_676
C23 C25 1.335(10) 2_676
C23 C23 1.366(12) 2_676
C23 C26 1.403(16) 2_676
C23 C27 1.426(11) 2_676
C23 C24 1.504(18) 2_676
C28 C24 0.20(3) 2_676
C28 C23 1.339(13) 2_676
C28 C25 1.383(15) 2_676
C28 C27 1.498(15) .
C26 C29 0.18(2) 2_676
C26 C25 1.313(17) .
C26 C27 1.34(2) .
C26 C23 1.403(16) 2_676
C25 C23 1.335(10) 2_676
C25 C28 1.382(15) 2_676
C25 C29 1.477(17) 2_676
C27 C29 1.30(2) 2_676
C27 C23 1.426(11) 2_676
C27 C24 1.448(16) 2_676
