#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/52/2015241.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2015241
loop_
_publ_author_name
'Camerman, Arthur '
'Hempel, Andrew'
'Mastropaolo, Donald'
'Camerman, Norman'
_publ_section_title
;
 N-Phenyl-N'-pyridylureas: stereochemical basis for
 anticonvulsant activity
;
_journal_coeditor_code           GD1429
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o190
_journal_page_last               o192
_journal_paper_doi               10.1107/S0108270106005543
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C13 H13 Cl N3 O +, Cl -'
_chemical_formula_moiety         'C13 H13 Cl N3 O +, Cl -'
_chemical_formula_sum            'C13 H13 Cl2 N3 O'
_chemical_formula_weight         298.16
_chemical_name_systematic
;
4-[N-(2-Chloro-6-methylphenyl)ureido]pyridinium chloride
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_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                69.06(3)
_cell_angle_beta                 81.29(2)
_cell_angle_gamma                80.60(3)
_cell_formula_units_Z            4
_cell_length_a                   8.022(3)
_cell_length_b                   13.193(4)
_cell_length_c                   14.893(4)
_cell_measurement_reflns_used    32
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      45
_cell_measurement_theta_min      19
_cell_volume                     1444.9(9)
_computing_cell_refinement       'Picker Operating Manual'
_computing_data_collection       'Picker Operating Manual (Picker, 1967)'
_computing_data_reduction        'DATRDN (Stewart, 1976)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Picker FACS-1 four-circle'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  'Ni-filtered radiation'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0052
_diffrn_reflns_av_sigmaI/netI    0.0584
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4418
_diffrn_reflns_theta_full        60.00
_diffrn_reflns_theta_max         60.00
_diffrn_reflns_theta_min         3.19
_diffrn_standards_decay_%        2.7
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.009
_exptl_absorpt_correction_T_max  0.724
_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.153
_refine_ls_extinction_coef       0.0062(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         4272
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      0.943
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0837P)²+0.3467P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_ref         0.1344
_reflns_number_gt                3375
_reflns_number_total             4272
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd1429.cif
_cod_data_source_block           I
_cod_database_code               2015241
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1A -0.1968(5) 0.4567(3) -0.0898(3) 0.0664(9) Uani d . 1
H H1A -0.3126 0.4760 -0.0950 0.081(4) Uiso calc R 1
C C2A -0.1406(5) 0.3730(2) -0.0096(2) 0.0564(8) Uani d . 1
C C3A 0.0313(4) 0.3437(2) -0.0020(2) 0.0489(7) Uani d . 1
C C4A 0.1474(5) 0.4004(2) -0.0743(2) 0.0575(8) Uani d D 1
C C5A 0.0879(6) 0.4843(3) -0.1535(2) 0.0696(10) Uani d . 1
H H5A 0.1646 0.5231 -0.2019 0.081(4) Uiso calc R 1
C C6A -0.0831(6) 0.5110(3) -0.1614(3) 0.0703(10) Uani d . 1
H H6A -0.1215 0.5664 -0.2158 0.081(4) Uiso calc R 1
C C7A 0.344(2) 0.3784(18) -0.078(3) 0.047(4) Uani d PD 0.419(6)
H H7A1 0.3770 0.3169 -0.0187 0.114(16) Uiso calc PR 0.209(3)
H H7A2 0.3905 0.4456 -0.0817 0.114(16) Uiso calc PR 0.209(3)
H H7A3 0.3906 0.3583 -0.1365 0.114(16) Uiso calc PR 0.209(3)
H H7A4 0.3951 0.4303 -0.1393 0.114(16) Uiso calc PR 0.209(3)
H H7A5 0.3816 0.3016 -0.0762 0.114(16) Uiso calc PR 0.209(3)
H H7A6 0.3815 0.3889 -0.0214 0.114(16) Uiso calc PR 0.209(3)
Cl Cl7A 0.3601(7) 0.3663(5) -0.0628(6) 0.093(2) Uani d P 0.581(6)
N N8A 0.0919(4) 0.25512(19) 0.07822(19) 0.0569(7) Uani d . 1
H H8A 0.1330 0.2680 0.1226 0.081(4) Uiso calc R 1
C C9A 0.0852(4) 0.1504(2) 0.0853(2) 0.0470(7) Uani d . 1
O O10A 0.0297(3) 0.12564(17) 0.02623(16) 0.0662(7) Uani d . 1
N N11A 0.1474(3) 0.07603(18) 0.16927(17) 0.0486(6) Uani d . 1
H H11A 0.1826 0.1035 0.2063 0.081(4) Uiso calc R 1
C C12A 0.1596(4) -0.0351(2) 0.2002(2) 0.0455(7) Uani d . 1
C C13A 0.1199(5) -0.0949(2) 0.1476(2) 0.0581(8) Uani d . 1
H H13A 0.0819 -0.0596 0.0868 0.081(4) Uiso calc R 1
C C14A 0.1377(5) -0.2058(3) 0.1867(3) 0.0698(10) Uani d . 1
H H14A 0.1094 -0.2461 0.1523 0.081(4) Uiso calc R 1
N N15A 0.1941(4) -0.2580(2) 0.2723(2) 0.0667(8) Uani d . 1
H H15A 0.2050 -0.3282 0.2947 0.081(4) Uiso calc R 1
C C16A 0.2343(5) -0.2035(3) 0.3240(3) 0.0647(9) Uani d . 1
H H16A 0.2736 -0.2418 0.3841 0.081(4) Uiso calc R 1
C C17A 0.2187(4) -0.0931(2) 0.2905(2) 0.0572(8) Uani d . 1
H H17A 0.2472 -0.0557 0.3274 0.081(4) Uiso calc R 1
C C18A -0.274(3) 0.3075(17) 0.0658(17) 0.107(11) Uani d P 0.581(6)
H H18A -0.2155 0.2510 0.1201 0.114(16) Uiso calc PR 0.291(3)
H H18B -0.3351 0.2708 0.0345 0.114(16) Uiso calc PR 0.291(3)
H H18C -0.3572 0.3583 0.0913 0.114(16) Uiso calc PR 0.291(3)
H H18D -0.3896 0.3357 0.0438 0.114(16) Uiso calc PR 0.291(3)
H H18E -0.2701 0.3160 0.1295 0.114(16) Uiso calc PR 0.291(3)
H H18F -0.2480 0.2285 0.0726 0.114(16) Uiso calc PR 0.291(3)
Cl Cl1A -0.2849(11) 0.3131(6) 0.0812(7) 0.0863(17) Uani d P 0.419(6)
C C1B 0.7192(6) -0.2579(3) 0.3600(3) 0.0815(12) Uani d . 1
H H1B 0.7411 -0.3191 0.4142 0.080(4) Uiso calc R 1
C C2B 0.6887(4) -0.1550(3) 0.3675(3) 0.0580(8) Uani d . 1
C C3B 0.6620(4) -0.0630(2) 0.2857(2) 0.0469(7) Uani d . 1
C C4B 0.6565(5) -0.0767(3) 0.1978(2) 0.0591(8) Uani d . 1
C C5B 0.6860(6) -0.1799(3) 0.1924(3) 0.0827(12) Uani d . 1
H H5B 0.6849 -0.1892 0.1335 0.080(4) Uiso calc R 1
C C6B 0.7171(7) -0.2696(3) 0.2731(4) 0.0952(15) Uani d . 1
H H6B 0.7369 -0.3390 0.2682 0.080(4) Uiso calc R 1
C C7B 0.638(3) 0.0211(16) 0.1086(14) 0.122(11) Uani d PU 0.603(5)
H H7B1 0.6117 0.0886 0.1266 0.114(16) Uiso calc PR 0.301(3)
H H7B2 0.5436 0.0154 0.0745 0.114(16) Uiso calc PR 0.301(3)
H H7B3 0.7464 0.0249 0.0650 0.114(16) Uiso calc PR 0.301(3)
H H7B4 0.6561 -0.0026 0.0508 0.114(16) Uiso calc PR 0.301(3)
H H7B5 0.7242 0.0706 0.1029 0.114(16) Uiso calc PR 0.301(3)
H H7B6 0.5214 0.0610 0.1124 0.114(16) Uiso calc PR 0.301(3)
Cl Cl7B 0.6024(11) 0.0360(5) 0.0992(4) 0.0797(13) Uani d P 0.397(5)
N N8B 0.6264(3) 0.04257(19) 0.29224(18) 0.0487(6) Uani d . 1
H H8B 0.5312 0.0801 0.2750 0.080(4) Uiso calc R 1
C C9B 0.7349(4) 0.0884(2) 0.3244(2) 0.0462(7) Uani d . 1
O O10B 0.8778(3) 0.05029(18) 0.34184(19) 0.0645(6) Uani d . 1
N N11B 0.6573(3) 0.18678(19) 0.33408(18) 0.0479(6) Uani d . 1
H H11B 0.5549 0.2070 0.3187 0.080(4) Uiso calc R 1
C C12B 0.7257(4) 0.2544(2) 0.3652(2) 0.0432(6) Uani d . 1
C C13B 0.8944(4) 0.2432(3) 0.3830(2) 0.0554(8) Uani d . 1
H H13B 0.9699 0.1848 0.3752 0.080(4) Uiso calc R 1
C C14B 0.9480(5) 0.3176(3) 0.4116(3) 0.0672(10) Uani d . 1
H H14B 1.0618 0.3111 0.4210 0.080(4) Uiso calc R 1
N N15B 0.8428(4) 0.3992(2) 0.4266(2) 0.0659(8) Uani d . 1
H H15B 0.8800 0.4443 0.4464 0.080(4) Uiso calc R 1
C C16B 0.6799(5) 0.4130(3) 0.4116(2) 0.0612(9) Uani d . 1
H H16B 0.6080 0.4707 0.4235 0.080(4) Uiso calc R 1
C C17B 0.6170(4) 0.3442(2) 0.3791(2) 0.0501(7) Uani d . 1
H H17B 0.5042 0.3561 0.3662 0.080(4) Uiso calc R 1
C C18B 0.701(4) -0.144(3) 0.466(2) 0.074(11) Uani d P 0.397(5)
H H18G 0.6752 -0.0655 0.4608 0.114(16) Uiso calc PR 0.199(3)
H H18H 0.8190 -0.1719 0.4854 0.114(16) Uiso calc PR 0.199(3)
H H18I 0.6182 -0.1878 0.5161 0.114(16) Uiso calc PR 0.199(3)
H H18J 0.7331 -0.2179 0.5141 0.114(16) Uiso calc PR 0.199(3)
H H18K 0.5893 -0.1116 0.4895 0.114(16) Uiso calc PR 0.199(3)
H H18L 0.7900 -0.0956 0.4587 0.114(16) Uiso calc PR 0.199(3)
Cl Cl1B 0.6720(9) -0.1409(5) 0.4801(5) 0.0761(14) Uani d P 0.603(5)
Cl Cl1 0.78591(10) 0.49808(6) 0.59447(6) 0.0552(3) Uani d . 1
Cl Cl2 0.29829(10) 0.21846(6) 0.26294(6) 0.0625(3) Uani d . 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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_site_symmetry_1
_geom_angle
C6A C1A C2A . 120.2(4)
C6A C1A H1A . 119.9
C2A C1A H1A . 119.9
C1A C2A C3A . 120.0(3)
C1A C2A C18A . 118.3(8)
C3A C2A C18A . 121.4(8)
C1A C2A Cl1A . 118.9(4)
C3A C2A Cl1A . 120.9(4)
C2A C3A C4A . 119.8(3)
C2A C3A N8A . 120.9(3)
C4A C3A N8A . 119.3(3)
C5A C4A C3A . 119.1(3)
C5A C4A C7A . 114.1(13)
C3A C4A C7A . 126.8(13)
C5A C4A Cl7A . 121.4(4)
C3A C4A Cl7A . 119.5(4)
C6A C5A C4A . 120.7(3)
C6A C5A H5A . 119.7
C4A C5A H5A . 119.7
C1A C6A C5A . 120.3(3)
C1A C6A H6A . 119.9
C5A C6A H6A . 119.9
C4A C7A H7A1 . 109.5
C4A C7A H7A2 . 109.5
H7A1 C7A H7A2 . 109.5
C4A C7A H7A3 . 109.5
H7A1 C7A H7A3 . 109.5
H7A2 C7A H7A3 . 109.5
C4A C7A H7A4 . 109.5
H7A1 C7A H7A4 . 141.1
H7A2 C7A H7A4 . 56.3
H7A3 C7A H7A4 . 56.3
C4A C7A H7A5 . 109.5
H7A1 C7A H7A5 . 56.3
H7A2 C7A H7A5 . 141.1
H7A3 C7A H7A5 . 56.3
H7A4 C7A H7A5 . 109.5
C4A C7A H7A6 . 109.5
H7A1 C7A H7A6 . 56.3
H7A2 C7A H7A6 . 56.3
H7A3 C7A H7A6 . 141.1
H7A4 C7A H7A6 . 109.5
H7A5 C7A H7A6 . 109.5
C9A N8A C3A . 120.5(2)
C9A N8A H8A . 119.8
C3A N8A H8A . 119.8
O10A C9A N8A 1 123.8(3)
O10A C9A N8A . 123.8(3)
O10A C9A N11A 1 124.4(3)
O10A C9A N11A . 124.4(3)
N8A C9A N11A . 111.8(2)
C12A N11A C9A . 128.0(2)
C12A N11A H11A . 116.0
C9A N11A H11A . 116.0
N11A C12A C13A . 124.6(3)
N11A C12A C17A . 117.6(3)
C13A C12A C17A . 117.8(3)
C14A C13A C12A . 118.8(3)
C14A C13A H13A . 120.6
C12A C13A H13A . 120.6
N15A C14A C13A . 121.7(3)
N15A C14A H14A . 119.1
C13A C14A H14A . 119.1
C14A N15A C16A . 121.0(3)
C14A N15A H15A . 119.5
C16A N15A H15A . 119.5
N15A C16A C17A . 120.8(3)
N15A C16A H16A . 119.6
C17A C16A H16A . 119.6
C16A C17A C12A . 119.8(3)
C16A C17A H17A . 120.1
C12A C17A H17A . 120.1
C2A C18A H18A . 109.5
C2A C18A H18B . 109.5
H18A C18A H18B . 109.5
C2A C18A H18C . 109.5
H18A C18A H18C . 109.5
H18B C18A H18C . 109.5
C2A C18A H18D . 109.5
H18A C18A H18D . 141.1
H18B C18A H18D . 56.3
H18C C18A H18D . 56.3
C2A C18A H18E . 109.5
H18A C18A H18E . 56.3
H18B C18A H18E . 141.1
H18C C18A H18E . 56.3
H18D C18A H18E . 109.5
C2A C18A H18F . 109.5
H18A C18A H18F . 56.3
H18B C18A H18F . 56.3
H18C C18A H18F . 141.1
H18D C18A H18F . 109.5
H18E C18A H18F . 109.5
C6B C1B C2B . 119.9(4)
C6B C1B H1B . 120.1
C2B C1B H1B . 120.1
C1B C2B C3B . 120.2(3)
C1B C2B C18B . 118.5(12)
C3B C2B C18B . 121.1(12)
C1B C2B Cl1B . 119.9(4)
C3B C2B Cl1B . 119.9(3)
C2B C3B C4B . 119.1(3)
C2B C3B N8B . 121.1(3)
C4B C3B N8B . 119.6(3)
C5B C4B C3B . 119.5(3)
C5B C4B C7B . 120.6(9)
C3B C4B C7B . 119.6(9)
C5B C4B Cl7B . 121.3(4)
C3B C4B Cl7B . 119.1(3)
C6B C5B C4B . 120.7(4)
C6B C5B H5B . 119.6
C4B C5B H5B . 119.6
C1B C6B C5B . 120.6(3)
C1B C6B H6B . 119.7
C5B C6B H6B . 119.7
C4B C7B H7B1 . 109.5
C4B C7B H7B2 . 109.5
H7B1 C7B H7B2 . 109.5
C4B C7B H7B3 . 109.5
H7B1 C7B H7B3 . 109.5
H7B2 C7B H7B3 . 109.5
C4B C7B H7B4 . 109.5
H7B1 C7B H7B4 . 141.1
H7B2 C7B H7B4 . 56.3
H7B3 C7B H7B4 . 56.3
C4B C7B H7B5 . 109.5
H7B1 C7B H7B5 . 56.3
H7B2 C7B H7B5 . 141.1
H7B3 C7B H7B5 . 56.3
H7B4 C7B H7B5 . 109.5
C4B C7B H7B6 . 109.5
H7B1 C7B H7B6 . 56.3
H7B2 C7B H7B6 . 56.3
H7B3 C7B H7B6 . 141.1
H7B4 C7B H7B6 . 109.5
H7B5 C7B H7B6 . 109.5
C9B N8B C3B . 123.5(3)
C9B N8B H8B . 118.3
C3B N8B H8B . 118.3
O10B C9B N8B 1 125.4(3)
O10B C9B N8B . 125.4(3)
O10B C9B N11B 1 124.2(3)
O10B C9B N11B . 124.2(3)
N8B C9B N11B . 110.4(3)
C12B N11B C9B . 127.0(3)
C12B N11B H11B . 116.5
C9B N11B H11B . 116.5
N11B C12B C13B . 125.4(3)
N11B C12B C17B . 117.0(3)
C13B C12B C17B . 117.5(3)
C14B C13B C12B . 119.7(3)
C14B C13B H13B . 120.1
C12B C13B H13B . 120.1
N15B C14B C13B . 121.6(3)
N15B C14B H14B . 119.2
C13B C14B H14B . 119.2
C14B N15B C16B . 121.1(3)
C14B N15B H15B . 119.4
C16B N15B H15B . 119.4
N15B C16B C17B . 121.1(3)
N15B C16B H16B . 119.5
C17B C16B H16B . 119.5
C16B C17B C12B . 118.9(3)
C16B C17B H17B . 120.5
C12B C17B H17B . 120.5
C2B C18B H18G . 109.5
C2B C18B H18H . 109.5
H18G C18B H18H . 109.5
C2B C18B H18I . 109.5
H18G C18B H18I . 109.5
H18H C18B H18I . 109.5
C2B C18B H18J . 109.5
H18G C18B H18J . 141.1
H18H C18B H18J . 56.3
H18I C18B H18J . 56.3
C2B C18B H18K . 109.5
H18G C18B H18K . 56.3
H18H C18B H18K . 141.1
H18I C18B H18K . 56.3
H18J C18B H18K . 109.5
C2B C18B H18L . 109.5
H18G C18B H18L . 56.3
H18H C18B H18L . 56.3
H18I C18B H18L . 141.1
H18J C18B H18L . 109.5
H18K C18B H18L . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1A C6A . 1.362(6)
C1A C2A . 1.381(5)
C1A H1A . 0.9300
C2A C3A . 1.381(5)
C2A C18A . 1.55(2)
C2A Cl1A . 1.689(8)
C3A C4A . 1.391(5)
C3A N8A . 1.422(4)
C4A C5A . 1.381(5)
C4A C7A . 1.551(18)
C4A Cl7A . 1.711(7)
C5A C6A . 1.372(6)
C5A H5A . 0.9300
C6A H6A . 0.9300
C7A H7A1 . 1.0000
C7A H7A2 . 1.0000
C7A H7A3 . 1.0000
C7A H7A4 . 1.0000
C7A H7A5 . 1.0000
C7A H7A6 . 1.0000
N8A C9A . 1.356(4)
N8A H8A . 0.8600
C9A O10A 1 1.204(3)
C9A O10A . 1.204(3)
C9A N11A . 1.389(4)
N11A C12A . 1.362(4)
N11A H11A . 0.8600
C12A C13A . 1.392(4)
C12A C17A . 1.400(4)
C13A C14A . 1.360(5)
C13A H13A . 0.9300
C14A N15A . 1.323(5)
C14A H14A . 0.9300
N15A C16A . 1.327(5)
N15A H15A . 0.8600
C16A C17A . 1.352(4)
C16A H16A . 0.9300
C17A H17A . 0.9300
C18A H18A . 1.0000
C18A H18B . 1.0000
C18A H18C . 1.0000
C18A H18D . 1.0000
C18A H18E . 1.0000
C18A H18F . 1.0000
C1B C6B . 1.360(6)
C1B C2B . 1.381(5)
C1B H1B . 0.9300
C2B C3B . 1.393(5)
C2B C18B . 1.55(3)
C2B Cl1B . 1.735(6)
C3B C4B . 1.393(4)
C3B N8B . 1.410(3)
C4B C5B . 1.372(5)
C4B C7B . 1.491(19)
C4B Cl7B . 1.726(7)
C5B C6B . 1.372(6)
C5B H5B . 0.9300
C6B H6B . 0.9300
C7B H7B1 . 1.0000
C7B H7B2 . 1.0000
C7B H7B3 . 1.0000
C7B H7B4 . 1.0000
C7B H7B5 . 1.0000
C7B H7B6 . 1.0000
N8B C9B . 1.362(4)
N8B H8B . 0.8600
C9B O10B 1 1.201(4)
C9B O10B . 1.201(4)
C9B N11B . 1.392(4)
N11B C12B . 1.357(4)
N11B H11B . 0.8600
C12B C13B . 1.393(4)
C12B C17B . 1.411(4)
C13B C14B . 1.349(4)
C13B H13B . 0.9300
C14B N15B . 1.319(5)
C14B H14B . 0.9300
N15B C16B . 1.331(5)
N15B H15B . 0.8600
C16B C17B . 1.361(4)
C16B H16B . 0.9300
C17B H17B . 0.9300
C18B H18G . 1.0000
C18B H18H . 1.0000
C18B H18I . 1.0000
C18B H18J . 1.0000
C18B H18K . 1.0000
C18B H18L . 1.0000
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N8A H8A Cl2 1 0.86 2.48 3.273(3) 154
N8B H8B Cl2 1 0.86 2.37 3.183(3) 158
N11A H11A Cl2 1 0.86 2.34 3.173(3) 163
N11B H11B Cl2 1 0.86 2.30 3.131(3) 164
N15A H15A Cl1 2_656 0.86 2.26 3.072(3) 158
N15B H15B Cl1 1 0.86 2.53 3.155(3) 131
N15B H15B Cl1 2_766 0.86 2.82 3.397(3) 126
C13A H13A O10A 1 0.93 2.27 2.864(4) 121
C13A H13A O10A 2 0.93 2.48 3.186(4) 133
C13B H13B O10B 1 0.93 2.26 2.850(4) 121
