#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/68/4506867.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_4506867
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 H16 Cl2 O'
_chemical_formula_weight         355.24
_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                 107.3880(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1079(5)
_cell_length_b                   17.6794(12)
_cell_length_c                   12.3042(8)
_cell_measurement_reflns_used    6375
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.01
_cell_measurement_theta_min      2.63
_cell_volume                     1683.12(19)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0166
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17199
_diffrn_reflns_theta_full        26.01
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.390
_exptl_absorpt_correction_T_max  0.9157
_exptl_absorpt_correction_T_min  0.8597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS - Bruker Nonius area detector scaling and absorption correction - V2.10'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3306
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0292
_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)+(0.0453P)²+0.7242P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0807
_reflns_number_gt                3068
_reflns_number_total             3306
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg3010097_si_003.cif
_cod_data_source_block           CMF-II
_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_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               4506867
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_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
Cl1 Cl 0.17300(4) 0.436523(19) 0.58068(3) 0.02352(11) Uani 1 1 d .
Cl2 Cl 0.85361(4) 0.505705(19) 0.69901(3) 0.02528(11) Uani 1 1 d .
O1 O 0.48929(13) 0.52447(5) 0.68521(8) 0.0234(2) Uani 1 1 d .
C1 C 0.51543(16) 0.46770(7) 0.63555(11) 0.0181(3) Uani 1 1 d .
C10 C 0.88728(17) 0.32903(8) 0.28541(12) 0.0228(3) Uani 1 1 d .
H10 H 0.8993 0.3725 0.2430 0.027 Uiso 1 1 calc R
C5 C 0.41082(17) 0.34885(7) 0.53047(11) 0.0189(3) Uani 1 1 d .
H5 H 0.3199 0.3135 0.5022 0.023 Uiso 1 1 calc R
C17 C 0.32759(17) 0.06433(7) 0.47695(12) 0.0199(3) Uani 1 1 d .
C3 C 0.71460(17) 0.38668(7) 0.56822(11) 0.0199(3) Uani 1 1 d .
H3 H 0.8257 0.3795 0.5589 0.024 Uiso 1 1 calc R
C19 C 0.46739(17) 0.14767(8) 0.37546(11) 0.0207(3) Uani 1 1 d .
H19 H 0.5006 0.1584 0.3093 0.025 Uiso 1 1 calc R
C6 C 0.37995(16) 0.41306(8) 0.57983(11) 0.0184(3) Uani 1 1 d .
C15 C 0.46450(17) 0.17940(8) 0.56502(11) 0.0212(3) Uani 1 1 d .
H15 H 0.4947 0.2124 0.6288 0.025 Uiso 1 1 calc R
C2 C 0.68565(17) 0.44719(7) 0.62655(11) 0.0193(3) Uani 1 1 d .
C4 C 0.57962(17) 0.33287(7) 0.51989(11) 0.0192(3) Uani 1 1 d .
C7 C 0.61247(17) 0.26728(7) 0.46670(11) 0.0196(3) Uani 1 1 d .
C14 C 0.51165(17) 0.19829(7) 0.46753(11) 0.0193(3) Uani 1 1 d .
C9 C 0.76884(17) 0.33014(7) 0.34620(11) 0.0216(3) Uani 1 1 d .
H9 H 0.7020 0.3743 0.3458 0.026 Uiso 1 1 calc R
C12 C 0.96793(18) 0.20253(8) 0.34733(12) 0.0255(3) Uani 1 1 d .
H12 H 1.0367 0.1588 0.3487 0.031 Uiso 1 1 calc R
C8 C 0.74655(17) 0.26650(7) 0.40852(11) 0.0200(3) Uani 1 1 d .
C11 C 0.98953(17) 0.26576(8) 0.28467(12) 0.0232(3) Uani 1 1 d .
C20 C 1.1182(2) 0.26592(9) 0.21832(13) 0.0311(3) Uani 1 1 d .
H20A H 1.0694 0.2930 0.1463 0.047 Uiso 1 1 calc R
H20B H 1.1445 0.2137 0.2025 0.047 Uiso 1 1 calc R
H20C H 1.2245 0.2912 0.2629 0.047 Uiso 1 1 calc R
C13 C 0.84832(18) 0.20247(8) 0.40728(12) 0.0233(3) Uani 1 1 d .
H13 H 0.8348 0.1585 0.4482 0.028 Uiso 1 1 calc R
C18 C 0.37603(17) 0.08234(8) 0.38013(11) 0.0213(3) Uani 1 1 d .
H18 H 0.3457 0.0491 0.3165 0.026 Uiso 1 1 calc R
C16 C 0.37474(18) 0.11342(8) 0.56982(11) 0.0214(3) Uani 1 1 d .
H16 H 0.3451 0.1015 0.6369 0.026 Uiso 1 1 calc R
C21 C 0.22635(19) -0.00658(8) 0.48003(13) 0.0248(3) Uani 1 1 d .
H21A H 0.2318 -0.0180 0.5590 0.037 Uiso 1 1 calc R
H21B H 0.2757 -0.0488 0.4485 0.037 Uiso 1 1 calc R
H21C H 0.1056 0.0009 0.4347 0.037 Uiso 1 1 calc R
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
O1 C1 C2 123.24(12)
O1 C1 C6 123.65(12)
C2 C1 C6 113.10(11)
C9 C10 C11 121.71(13)
C9 C10 H10 119.1
C11 C10 H10 119.1
C6 C5 C4 121.06(12)
C6 C5 H5 119.5
C4 C5 H5 119.5
C16 C17 C18 118.59(12)
C16 C17 C21 121.05(12)
C18 C17 C21 120.36(12)
C2 C3 C4 120.89(12)
C2 C3 H3 119.6
C4 C3 H3 119.6
C18 C19 C14 120.67(12)
C18 C19 H19 119.7
C14 C19 H19 119.7
C5 C6 C1 123.44(12)
C5 C6 Cl1 121.07(10)
C1 C6 Cl1 115.49(9)
C16 C15 C14 121.16(12)
C16 C15 H15 119.4
C14 C15 H15 119.4
C3 C2 C1 123.76(12)
C3 C2 Cl2 120.90(11)
C1 C2 Cl2 115.33(10)
C7 C4 C3 121.02(12)
C7 C4 C5 121.65(12)
C3 C4 C5 117.32(12)
C4 C7 C8 120.58(12)
C4 C7 C14 120.11(12)
C8 C7 C14 119.31(12)
C19 C14 C15 117.95(12)
C19 C14 C7 122.14(12)
C15 C14 C7 119.83(12)
C10 C9 C8 120.53(12)
C10 C9 H9 119.7
C8 C9 H9 119.7
C13 C12 C11 121.20(13)
C13 C12 H12 119.4
C11 C12 H12 119.4
C9 C8 C13 117.94(12)
C9 C8 C7 119.57(12)
C13 C8 C7 122.39(12)
C10 C11 C12 117.72(13)
C10 C11 C20 120.81(13)
C12 C11 C20 121.47(13)
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
C12 C13 C8 120.90(13)
C12 C13 H13 119.6
C8 C13 H13 119.6
C19 C18 C17 121.07(12)
C19 C18 H18 119.5
C17 C18 H18 119.5
C15 C16 C17 120.53(12)
C15 C16 H16 119.7
C17 C16 H16 119.7
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
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C6 1.7315(13)
Cl2 C2 1.7303(13)
O1 C1 1.2261(16)
C1 C2 1.4628(18)
C1 C6 1.4695(18)
C10 C9 1.3825(19)
C10 C11 1.394(2)
C10 H10 0.9500
C5 C6 1.3457(19)
C5 C4 1.4410(18)
C5 H5 0.9500
C17 C16 1.3943(19)
C17 C18 1.3980(19)
C17 C21 1.5051(19)
C3 C2 1.3473(19)
C3 C4 1.4378(19)
C3 H3 0.9500
C19 C18 1.3826(19)
C19 C14 1.4036(19)
C19 H19 0.9500
C15 C16 1.3856(19)
C15 C14 1.4037(19)
C15 H15 0.9500
C4 C7 1.3958(18)
C7 C8 1.4696(18)
C7 C14 1.4700(19)
C9 C8 1.4033(19)
C9 H9 0.9500
C12 C13 1.383(2)
C12 C11 1.398(2)
C12 H12 0.9500
C8 C13 1.4035(19)
C11 C20 1.5047(19)
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
C13 H13 0.9500
C18 H18 0.9500
C16 H16 0.9500
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652481
2 PubChem 102347176
