#------------------------------------------------------------------------------
#$Date: 2016-08-07 11:12:28 +0300 (Sun, 07 Aug 2016) $
#$Revision: 185184 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/56/7225695.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_7225695
loop_
_publ_author_name
'Sovago, Ioana'
'Thomas, Lynne H.'
'Adam, Martin S.'
'Capelli, Silvia C.'
'Wilson, Chick C.'
'Farrugia, Louis J.'
_publ_section_title
;
 High resolution X-ray and neutron diffraction studies on molecular
 complexes of chloranilic acid and lutidines
;
_journal_issue                   30
_journal_name_full               CrystEngComm
_journal_page_first              5697
_journal_paper_doi               10.1039/C6CE01065B
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety
;
C6 Cl2 O4, 0.5(C6 H4 Cl2 O4), C7 H10 N
;
_chemical_formula_sum            'C16 H12 Cl3 N O6'
_chemical_formula_weight         420.62
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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_update_record
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                71.632(2)
_cell_angle_beta                 88.044(2)
_cell_angle_gamma                86.436(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0154(3)
_cell_length_b                   9.3997(3)
_cell_length_c                   11.8524(5)
_cell_measurement_reflns_used    4974
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.23
_cell_measurement_theta_min      1.811
_cell_measurement_wavelength     0.71073
_cell_volume                     845.75(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.0082621
_diffrn_orient_matrix_UB_12      -0.0382719
_diffrn_orient_matrix_UB_13      -0.0698410
_diffrn_orient_matrix_UB_21      0.1197947
_diffrn_orient_matrix_UB_22      -0.0328348
_diffrn_orient_matrix_UB_23      0.0184451
_diffrn_orient_matrix_UB_31      -0.0347857
_diffrn_orient_matrix_UB_32      -0.1002994
_diffrn_orient_matrix_UB_33      0.0518375
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_av_unetI/netI     0.038
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4974
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_reduction_process
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.23
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.577
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4974
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0286P)²+0.4974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0814
_reflns_Friedel_coverage         0
_reflns_number_gt                4125
_reflns_number_total             4974
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce01065b3.cif
_cod_data_source_block           6_shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_space_group_crystal_system' value 'Triclinic' changed to
'triclinic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7225667--7225698.cif.
;
_cod_database_code               7225695
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
Cl1 Cl 0.36765(5) 0.29834(4) 0.75146(3) 0.02226(9) Uani 1 1 d
Cl2 Cl 0.29218(5) 0.53590(4) 0.16058(3) 0.02230(9) Uani 1 1 d
Cl3 Cl 0.13189(4) 0.13193(4) 0.02046(3) 0.01906(8) Uani 1 1 d
O2 O 0.53239(14) 0.19825(11) 0.55901(10) 0.0222(2) Uani 1 1 d
O3 O 0.65796(19) 0.36418(13) 0.35386(12) 0.0389(3) Uani 1 1 d
O12 O 0.29788(13) 0.58424(12) -0.10124(10) 0.0213(2) Uani 1 1 d
O13 O -0.05363(15) 0.44513(12) 0.23787(9) 0.0228(2) Uani 1 1 d
O32 O 0.24451(13) -0.13412(12) -0.05166(10) 0.0209(2) Uani 1 1 d
O33 O 0.44558(13) 0.25605(11) 0.06558(10) 0.0194(2) Uani 1 1 d
N125 N 0.73639(16) 0.02885(14) 0.45787(11) 0.0191(2) Uani 1 1 d
C121 C 0.8956(2) -0.04520(18) 0.31235(14) 0.0231(3) Uani 1 1 d
C122 C 0.94820(19) -0.17922(17) 0.39923(15) 0.0226(3) Uani 1 1 d
C123 C 0.8879(2) -0.20464(17) 0.51449(14) 0.0232(3) Uani 1 1 d
C124 C 0.7798(2) -0.09995(17) 0.54404(13) 0.0205(3) Uani 1 1 d
C126 C 0.7905(2) 0.05692(17) 0.34426(14) 0.0214(3) Uani 1 1 d
C22 C 1.0639(2) -0.2924(2) 0.3664(2) 0.0329(4) Uani 1 1 d
C24 C 0.7079(2) -0.1250(2) 0.66618(15) 0.0274(3) Uani 1 1 d
C111 C 0.43694(18) 0.40934(15) 0.61299(13) 0.0178(3) Uani 1 1 d
C112 C 0.51411(18) 0.33752(16) 0.53636(13) 0.0177(3) Uani 1 1 d
C113 C 0.58468(19) 0.43474(16) 0.41596(13) 0.0208(3) Uani 1 1 d
C211 C 0.13201(18) 0.51595(15) 0.07445(13) 0.0179(3) Uani 1 1 d
C212 C 0.16212(17) 0.54331(14) -0.04945(12) 0.0154(3) Uani 1 1 d
C213 C -0.02202(18) 0.47394(14) 0.12534(12) 0.0156(3) Uani 1 1 d
C311 C 0.33378(16) 0.06172(15) 0.01355(12) 0.0151(2) Uani 1 1 d
C312 C 0.35807(17) -0.07085(15) -0.02502(12) 0.0151(2) Uani 1 1 d
C313 C 0.46510(17) 0.13213(15) 0.03474(12) 0.0151(2) Uani 1 1 d
H121 H 0.930(2) -0.026(2) 0.2351(18) 0.022(5) Uiso 1 1 d
H123 H 0.918(2) -0.296(2) 0.5741(18) 0.025(5) Uiso 1 1 d
H125 H 0.673(3) 0.102(3) 0.476(2) 0.038(6) Uiso 1 1 d
H126 H 0.754(2) 0.152(2) 0.2906(18) 0.027(5) Uiso 1 1 d
H22A H 1.103(3) -0.369(3) 0.435(2) 0.052(7) Uiso 1 1 d
H22B H 1.008(3) -0.341(3) 0.325(2) 0.056(8) Uiso 1 1 d
H22C H 1.154(3) -0.244(3) 0.319(2) 0.052(7) Uiso 1 1 d
H24A H 0.788(3) -0.171(3) 0.724(2) 0.048(7) Uiso 1 1 d
H24B H 0.613(3) -0.188(3) 0.678(2) 0.047(7) Uiso 1 1 d
H24C H 0.671(3) -0.029(3) 0.680(2) 0.055(7) Uiso 1 1 d
H33 H 0.536(3) 0.293(2) 0.0689(19) 0.030(5) Uiso 1 1 d
H13 H -0.196(6) 0.418(6) 0.263(5) 0.169(19) Uiso 1 1 d
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
C213 O13 H13 113(2) . .
C313 O33 H33 112.4(14) . .
C126 N125 C124 122.28(13) . .
C126 N125 H125 117.7(14) . .
C124 N125 H125 119.9(14) . .
C126 C121 C122 119.45(15) . .
C126 C121 H121 119.6(12) . .
C122 C121 H121 120.9(12) . .
C123 C122 C121 118.16(14) . .
C123 C122 C22 121.48(15) . .
C121 C122 C22 120.35(16) . .
C122 C123 C124 121.16(14) . .
C122 C123 H123 119.8(12) . .
C124 C123 H123 119.1(12) . .
N125 C124 C123 118.37(14) . .
N125 C124 C24 118.77(14) . .
C123 C124 C24 122.85(14) . .
N125 C126 C121 120.55(14) . .
N125 C126 H126 115.4(12) . .
C121 C126 H126 124.0(12) . .
C122 C22 H22A 111.0(15) . .
C122 C22 H22B 110.4(16) . .
H22A C22 H22B 105(2) . .
C122 C22 H22C 110.3(15) . .
H22A C22 H22C 111(2) . .
H22B C22 H22C 109(2) . .
C124 C24 H24A 110.6(15) . .
C124 C24 H24B 109.8(14) . .
H24A C24 H24B 110(2) . .
C124 C24 H24C 111.9(15) . .
H24A C24 H24C 106(2) . .
H24B C24 H24C 109(2) . .
C113 C111 C112 123.16(13) 2_666 .
C113 C111 Cl1 118.76(11) 2_666 .
C112 C111 Cl1 118.07(11) . .
O2 C112 C111 124.54(13) . .
O2 C112 C113 116.81(13) . .
C111 C112 C113 118.64(12) . .
O3 C113 C111 126.29(14) . 2_666
O3 C113 C112 115.55(13) . .
C111 C113 C112 118.16(13) 2_666 .
C213 C211 C212 121.03(13) . .
C213 C211 Cl2 120.26(11) . .
C212 C211 Cl2 118.71(11) . .
O12 C212 C211 124.10(13) . .
O12 C212 C213 116.99(12) . 2_565
C211 C212 C213 118.90(12) . 2_565
O13 C213 C211 123.00(13) . .
O13 C213 C212 116.92(12) . 2_565
C211 C213 C212 120.07(12) . 2_565
C313 C311 C312 121.17(12) . .
C313 C311 Cl3 121.50(11) . .
C312 C311 Cl3 117.16(10) . .
O32 C312 C311 123.99(13) . .
O32 C312 C313 117.96(12) . 2_655
C311 C312 C313 118.04(11) . 2_655
O33 C313 C311 122.04(12) . .
O33 C313 C312 117.25(12) . 2_655
C311 C313 C312 120.72(12) . 2_655
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C111 1.7381(14) .
Cl2 C211 1.7221(14) .
Cl3 C311 1.7185(13) .
O2 C112 1.2508(17) .
O3 C113 1.2476(19) .
O12 C212 1.2516(17) .
O13 C213 1.2939(17) .
O13 H13 1.19(5) .
O32 C312 1.2195(17) .
O33 C313 1.3254(16) .
O33 H33 0.83(2) .
N125 C126 1.349(2) .
N125 C124 1.3500(19) .
N125 H125 0.91(2) .
C121 C126 1.372(2) .
C121 C122 1.404(2) .
C121 H121 0.911(19) .
C122 C123 1.386(2) .
C122 C22 1.502(2) .
C123 C124 1.390(2) .
C123 H123 0.95(2) .
C124 C24 1.493(2) .
C126 H126 0.96(2) .
C22 H22A 0.95(3) .
C22 H22B 0.91(3) .
C22 H22C 0.95(3) .
C24 H24A 0.94(3) .
C24 H24B 0.97(3) .
C24 H24C 0.99(3) .
C111 C113 1.3968(19) 2_666
C111 C112 1.400(2) .
C112 C113 1.542(2) .
C113 C111 1.3968(19) 2_666
C211 C213 1.380(2) .
C211 C212 1.424(2) .
C212 C213 1.5099(19) 2_565
C213 C212 1.5099(19) 2_565
C311 C313 1.3485(19) .
C311 C312 1.4568(19) .
C312 C313 1.5110(18) 2_655
C313 C312 1.5110(18) 2_655
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C126 C121 C122 C123 1.5(2) . .
C126 C121 C122 C22 -179.74(15) . .
C121 C122 C123 C124 -0.7(2) . .
C22 C122 C123 C124 -179.49(16) . .
C126 N125 C124 C123 1.9(2) . .
C126 N125 C124 C24 -177.14(15) . .
C122 C123 C124 N125 -0.9(2) . .
C122 C123 C124 C24 178.08(16) . .
C124 N125 C126 C121 -1.2(2) . .
C122 C121 C126 N125 -0.6(2) . .
C113 C111 C112 O2 -178.61(15) 2_666 .
Cl1 C111 C112 O2 2.3(2) . .
C113 C111 C112 C113 2.3(2) 2_666 .
Cl1 C111 C112 C113 -176.76(11) . .
O2 C112 C113 O3 -2.0(2) . .
C111 C112 C113 O3 177.16(15) . .
O2 C112 C113 C111 178.66(14) . 2_666
C111 C112 C113 C111 -2.2(2) . 2_666
C213 C211 C212 O12 178.67(13) . .
Cl2 C211 C212 O12 -1.46(19) . .
C213 C211 C212 C213 0.2(2) . 2_565
Cl2 C211 C212 C213 -179.96(9) . 2_565
C212 C211 C213 O13 178.59(13) . .
Cl2 C211 C213 O13 -1.28(19) . .
C212 C211 C213 C212 -0.2(2) . 2_565
Cl2 C211 C213 C212 179.96(10) . 2_565
C313 C311 C312 O32 -175.84(14) . .
Cl3 C311 C312 O32 -0.39(19) . .
C313 C311 C312 C313 3.0(2) . 2_655
Cl3 C311 C312 C313 178.48(10) . 2_655
C312 C311 C313 O33 177.44(13) . .
Cl3 C311 C313 O33 2.2(2) . .
C312 C311 C313 C312 -3.1(2) . 2_655
Cl3 C311 C313 C312 -178.36(10) . 2_655
