#------------------------------------------------------------------------------
#$Date: 2016-08-07 11:12:28 +0300 (Sun, 07 Aug 2016) $
#$Revision: 185184 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/56/7225693.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_7225693
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, 2(C7 H10 N), 2(H2 O)                                      
;
_chemical_formula_sum            'C20 H24 Cl2 N2 O6'
_chemical_formula_weight         459.33
_chemical_name_systematic
;                                                          
 ?                                                         
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_update_record
;
2016-05-04 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.620(14)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.036(2)
_cell_length_b                   7.6591(17)
_cell_length_c                   13.948(3)
_cell_measurement_reflns_used    2162
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.5
_cell_measurement_theta_min      2.1
_cell_measurement_wavelength     0.71073
_cell_volume                     1057.1(4)
_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 0.994
_diffrn_measured_fraction_theta_max 0.992
_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_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9350
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.474
_diffrn_reflns_theta_min         2.058
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  0.9659
_exptl_absorpt_correction_T_min  0.9169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker(2001)'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.065
_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     184
_refine_ls_number_reflns         2162
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0463P)²+0.0223P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0909
_refine_ls_wR_factor_ref         0.0991
_reflns_number_gt                1576
_reflns_number_total             2162
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce01065b3.cif
_cod_data_source_block           4_shelx
_cod_depositor_comments
'Adding full bibliography for 7225667--7225698.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7225693
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_calc_flag
Cl1 Cl 1.00408(6) -0.14013(7) 0.28608(4) 0.01976(18) Uani 1 d
O2 O 1.22351(15) 0.04717(19) 0.41886(11) 0.0193(4) Uani 1 d
O3 O 1.22001(15) 0.1593(2) 0.59733(11) 0.0204(4) Uani 1 d
O11 O 1.30185(18) 0.0722(2) 0.23511(14) 0.0240(4) Uani 1 d
N125 N 1.4523(2) 0.2085(2) 0.50150(14) 0.0187(4) Uani 1 d
C121 C 1.6393(2) 0.2997(3) 0.43417(17) 0.0208(5) Uani 1 d
C122 C 1.6969(2) 0.3743(3) 0.52211(17) 0.0173(5) Uani 1 d
C123 C 1.6271(2) 0.3643(3) 0.60130(16) 0.0171(5) Uani 1 d
C124 C 1.5044(2) 0.2791(3) 0.58746(18) 0.0194(5) Uani 1 d
C126 C 1.5169(2) 0.2169(3) 0.42505(18) 0.0204(5) Uani 1 d
C22 C 1.8298(3) 0.4674(4) 0.5322(2) 0.0253(6) Uani 1 d
C23 C 1.6809(3) 0.4421(4) 0.69788(19) 0.0253(6) Uani 1 d
C111 C 1.0013(2) -0.0605(3) 0.40239(16) 0.0165(5) Uani 1 d
C112 C 1.1165(2) 0.0203(3) 0.45196(16) 0.0161(5) Uani 1 d
C113 C 1.1155(2) 0.0863(3) 0.55620(16) 0.0159(5) Uani 1 d
H121 H 1.690(2) 0.308(3) 0.3778(17) 0.025(6) Uiso 1 d
H124 H 1.451(2) 0.263(3) 0.6408(17) 0.029(7) Uiso 1 d
H125 H 1.362(3) 0.155(3) 0.4892(19) 0.046(8) Uiso 1 d
H126 H 1.471(2) 0.166(3) 0.3665(18) 0.025(7) Uiso 1 d
H22A H 1.862(2) 0.464(3) 0.4714(19) 0.031(7) Uiso 1 d
H22B H 1.894(3) 0.414(3) 0.5809(18) 0.027(7) Uiso 1 d
H22C H 1.821(3) 0.585(4) 0.544(2) 0.049(9) Uiso 1 d
H23A H 1.708(2) 0.568(3) 0.6904(16) 0.026(7) Uiso 1 d
H23B H 1.759(3) 0.383(3) 0.732(2) 0.041(8) Uiso 1 d
H23C H 1.617(3) 0.440(3) 0.745(2) 0.047(8) Uiso 1 d
H11A H 1.249(3) 0.155(5) 0.203(3) 0.073(12) Uiso 1 d
H11B H 1.267(3) 0.052(4) 0.279(2) 0.038(9) Uiso 1 d
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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
H11A O11 H11B 104(3) . .
C126 N125 C124 121.6(2) . .
C126 N125 H125 115.8(16) . .
C124 N125 H125 122.4(16) . .
C126 C121 C122 120.5(2) . .
C126 C121 H121 121.3(14) . .
C122 C121 H121 118.3(14) . .
C121 C122 C123 118.9(2) . .
C121 C122 C22 120.8(2) . .
C123 C122 C22 120.3(2) . .
C124 C123 C122 117.8(2) . .
C124 C123 C23 119.8(2) . .
C122 C123 C23 122.4(2) . .
N125 C124 C123 121.5(2) . .
N125 C124 H124 116.1(14) . .
C123 C124 H124 122.3(14) . .
N125 C126 C121 119.7(2) . .
N125 C126 H126 115.7(14) . .
C121 C126 H126 124.6(15) . .
C122 C22 H22A 109.4(15) . .
C122 C22 H22B 110.6(15) . .
H22A C22 H22B 109(2) . .
C122 C22 H22C 111.5(18) . .
H22A C22 H22C 104(2) . .
H22B C22 H22C 112(2) . .
C123 C23 H23A 110.5(13) . .
C123 C23 H23B 113.8(16) . .
H23A C23 H23B 107(2) . .
C123 C23 H23C 114.6(16) . .
H23A C23 H23C 107(2) . .
H23B C23 H23C 103(2) . .
C112 C111 C113 122.7(2) . 3_756
C112 C111 Cl1 118.62(16) . .
C113 C111 Cl1 118.65(17) 3_756 .
O2 C112 C111 125.6(2) . .
O2 C112 C113 115.75(19) . .
C111 C112 C113 118.65(18) . .
O3 C113 C111 124.9(2) . 3_756
O3 C113 C112 116.45(18) . .
C111 C113 C112 118.7(2) 3_756 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C111 1.738(2) .
O2 C112 1.255(2) .
O3 C113 1.241(3) .
O11 H11A 0.90(4) .
O11 H11B 0.77(3) .
N125 C126 1.339(3) .
N125 C124 1.339(3) .
N125 H125 0.98(3) .
C121 C126 1.369(3) .
C121 C122 1.389(3) .
C121 H121 1.01(2) .
C122 C123 1.406(3) .
C122 C22 1.498(3) .
C123 C124 1.378(3) .
C123 C23 1.490(3) .
C124 H124 0.99(2) .
C126 H126 0.95(2) .
C22 H22A 0.96(2) .
C22 H22B 0.95(3) .
C22 H22C 0.92(3) .
C23 H23A 1.01(2) .
C23 H23B 0.96(3) .
C23 H23C 1.00(3) .
C111 C112 1.390(3) .
C111 C113 1.404(3) 3_756
C112 C113 1.541(3) .
C113 C111 1.404(3) 3_756
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 -0.4(3) . .
C126 C121 C122 C22 -179.1(2) . .
C121 C122 C123 C124 0.5(3) . .
C22 C122 C123 C124 179.2(2) . .
C121 C122 C123 C23 -179.4(2) . .
C22 C122 C123 C23 -0.7(3) . .
C126 N125 C124 C123 0.2(3) . .
C122 C123 C124 N125 -0.4(3) . .
C23 C123 C124 N125 179.5(2) . .
C124 N125 C126 C121 -0.2(3) . .
C122 C121 C126 N125 0.3(4) . .
C113 C111 C112 O2 -179.9(2) 3_756 .
Cl1 C111 C112 O2 2.5(3) . .
C113 C111 C112 C113 -0.7(4) 3_756 .
Cl1 C111 C112 C113 -178.28(15) . .
O2 C112 C113 O3 0.0(3) . .
C111 C112 C113 O3 -179.27(19) . .
O2 C112 C113 C111 179.95(19) . 3_756
C111 C112 C113 C111 0.7(3) . 3_756
