#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/48/2224855.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_2224855
loop_
_publ_author_name
'Jasinski, Jerry P.'
'Butcher, Ray J.'
'Hakim Al-Arique, Q. N. M.'
'Yathirajan, H. S.'
'Narayana, B.'
_publ_section_title
;
 Chlorimipraminium picrate
;
_journal_coeditor_code           BT5128
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o347
_journal_page_last               o348
_journal_paper_doi               10.1107/S1600536810000905
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C19 H24 Cl N2 +, C6 H2 N3 O7 -'
_chemical_formula_moiety         'C19 H24 Cl N2 +, C6 H2 N3 O7 -'
_chemical_formula_sum            'C25 H26 Cl N5 O7'
_chemical_formula_weight         543.96
_chemical_name_common            'Chlorimipraminium picrate'
_chemical_name_systematic
;3-Chloro-5-[3-(dimethylamino)propyl]-10,11-dihydro-5H-dibenz[b,f]azepinium
 picrate
;
_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
_cell_angle_alpha                90.9414(19)
_cell_angle_beta                 91.1253(19)
_cell_angle_gamma                100.4446(19)
_cell_formula_units_Z            4
_cell_length_a                   11.2252(3)
_cell_length_b                   13.1514(3)
_cell_length_c                   17.2787(4)
_cell_measurement_reflns_used    14780
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      32.6655
_cell_measurement_theta_min      4.6872
_cell_volume                     2507.54(11)
_computing_cell_refinement
'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_data_reduction
'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_molecular_graphics
'XP (Sheldrick, 2008) and Mercury (Macrae et al., 2006)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), enCIFer (Allen et al.,
2004)
and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 10.5081
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measurement_device_type
;
Oxford Diffraction Gemini R CCD
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0515
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32779
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.76
_diffrn_reflns_theta_min         4.69
_diffrn_standards_decay_%        <2%
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_correction_T_min  0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2007)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.534
_refine_diff_density_min         -0.478
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     689
_refine_ls_number_reflns         16481
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0635P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1153
_reflns_number_gt                10873
_reflns_number_total             16481
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5128.cif
_cod_data_source_block           I
_cod_original_cell_volume        2507.55(10)
_cod_database_code               2224855
_cod_database_fobs_code          2224855
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.59334(3) 0.87280(3) 0.92251(2) 0.03074(9) Uani d . 1 . .
N N1A 0.37421(9) 0.86170(8) 0.65507(6) 0.0172(2) Uani d . 1 . .
N N2A 0.64917(9) 0.73998(8) 0.53424(6) 0.0175(2) Uani d . 1 . .
H H2AB 0.6526 0.7035 0.5796 0.021 Uiso calc R 1 . .
C C1A 0.39922(10) 0.81199(9) 0.72519(7) 0.0166(2) Uani d . 1 . .
C C2A 0.47865(10) 0.86207(10) 0.78235(7) 0.0183(2) Uani d . 1 . .
H H2AA 0.5199 0.9309 0.7755 0.022 Uiso calc R 1 . .
C C3A 0.49670(11) 0.81002(10) 0.84951(7) 0.0198(3) Uani d . 1 . .
C C4A 0.43734(11) 0.71005(10) 0.86195(7) 0.0200(3) Uani d . 1 . .
H H4AA 0.4498 0.6760 0.9087 0.024 Uiso calc R 1 . .
C C5A 0.35871(11) 0.66092(10) 0.80371(8) 0.0210(3) Uani d . 1 . .
H H5AA 0.3167 0.5925 0.8114 0.025 Uiso calc R 1 . .
C C6A 0.34025(11) 0.70941(10) 0.73483(7) 0.0184(2) Uani d . 1 . .
C C7A 0.25976(12) 0.65622(10) 0.67027(8) 0.0240(3) Uani d . 1 . .
H H7AA 0.2404 0.5812 0.6802 0.029 Uiso calc R 1 . .
H H7AB 0.3038 0.6655 0.6211 0.029 Uiso calc R 1 . .
C C8A 0.14237(12) 0.69788(11) 0.66183(9) 0.0288(3) Uani d . 1 . .
H H8AA 0.0972 0.6631 0.6160 0.035 Uiso calc R 1 . .
H H8AB 0.0931 0.6765 0.7077 0.035 Uiso calc R 1 . .
C C9A 0.14981(11) 0.81328(10) 0.65337(7) 0.0212(3) Uani d . 1 . .
C C10A 0.03832(12) 0.84621(11) 0.64822(8) 0.0265(3) Uani d . 1 . .
H H10A -0.0339 0.7961 0.6512 0.032 Uiso calc R 1 . .
C C11A 0.02888(12) 0.94905(12) 0.63898(8) 0.0273(3) Uani d . 1 . .
H H11A -0.0484 0.9685 0.6342 0.033 Uiso calc R 1 . .
C C12A 0.13302(12) 1.02253(11) 0.63690(8) 0.0246(3) Uani d . 1 . .
H H12A 0.1281 1.0934 0.6314 0.030 Uiso calc R 1 . .
C C13A 0.24533(11) 0.99277(10) 0.64291(7) 0.0201(3) Uani d . 1 . .
H H13A 0.3168 1.0440 0.6420 0.024 Uiso calc R 1 . .
C C14A 0.25533(11) 0.88889(10) 0.65020(7) 0.0171(2) Uani d . 1 . .
C C15A 0.47414(11) 0.93650(10) 0.62436(8) 0.0192(2) Uani d . 1 . .
H H15A 0.4982 0.9939 0.6625 0.023 Uiso calc R 1 . .
H H15B 0.4462 0.9658 0.5763 0.023 Uiso calc R 1 . .
C C16A 0.58398(11) 0.88708(10) 0.60687(7) 0.0189(2) Uani d . 1 . .
H H16A 0.6517 0.9410 0.5906 0.023 Uiso calc R 1 . .
H H16B 0.6103 0.8554 0.6543 0.023 Uiso calc R 1 . .
C C17A 0.55383(11) 0.80490(10) 0.54323(7) 0.0191(2) Uani d . 1 . .
H H17A 0.4761 0.7595 0.5548 0.023 Uiso calc R 1 . .
H H17B 0.5429 0.8390 0.4936 0.023 Uiso calc R 1 . .
C C18A 0.77140(11) 0.80309(11) 0.52275(8) 0.0268(3) Uani d . 1 . .
H H18A 0.7975 0.8448 0.5696 0.040 Uiso calc R 1 . .
H H18B 0.7680 0.8488 0.4788 0.040 Uiso calc R 1 . .
H H18C 0.8292 0.7572 0.5122 0.040 Uiso calc R 1 . .
C C19A 0.61616(13) 0.66325(11) 0.46961(7) 0.0249(3) Uani d . 1 . .
H H19A 0.5368 0.6208 0.4790 0.037 Uiso calc R 1 . .
H H19B 0.6772 0.6188 0.4664 0.037 Uiso calc R 1 . .
H H19C 0.6127 0.6996 0.4208 0.037 Uiso calc R 1 . .
Cl Cl2 0.19710(4) 0.83645(3) 0.44656(2) 0.03975(10) Uani d . 1 . .
N N1B -0.00504(8) 0.84031(8) 0.17770(6) 0.0164(2) Uani d . 1 . .
N N2B 0.16727(9) 0.76659(8) 0.02222(6) 0.0194(2) Uani d . 1 . .
H H2BB 0.1600 0.7376 0.0710 0.023 Uiso calc R 1 . .
C C1B -0.00482(11) 0.79100(9) 0.25044(7) 0.0179(2) Uani d . 1 . .
C C2B 0.08559(11) 0.82856(10) 0.30604(7) 0.0196(2) Uani d . 1 . .
H H2BA 0.1479 0.8848 0.2941 0.024 Uiso calc R 1 . .
C C3B 0.08492(13) 0.78428(11) 0.37833(8) 0.0257(3) Uani d . 1 . .
C C4B -0.00406(14) 0.70222(12) 0.39755(9) 0.0322(3) Uani d . 1 . .
H H4BA -0.0046 0.6725 0.4473 0.039 Uiso calc R 1 . .
C C5B -0.09206(13) 0.66473(11) 0.34232(9) 0.0307(3) Uani d . 1 . .
H H5BA -0.1533 0.6081 0.3552 0.037 Uiso calc R 1 . .
C C6B -0.09587(11) 0.70576(10) 0.26812(9) 0.0242(3) Uani d . 1 . .
C C7B -0.19630(13) 0.65203(12) 0.21395(10) 0.0354(4) Uani d . 1 . .
H H7BA -0.2743 0.6529 0.2395 0.043 Uiso calc R 1 . .
H H7BB -0.1874 0.5787 0.2086 0.043 Uiso calc R 1 . .
C C8B -0.20590(12) 0.69393(11) 0.13257(9) 0.0299(3) Uani d . 1 . .
H H8BA -0.1331 0.6859 0.1033 0.036 Uiso calc R 1 . .
H H8BB -0.2777 0.6536 0.1050 0.036 Uiso calc R 1 . .
C C9B -0.21672(11) 0.80566(10) 0.13599(8) 0.0224(3) Uani d . 1 . .
C C10B -0.32578(12) 0.83958(12) 0.12103(8) 0.0283(3) Uani d . 1 . .
H H10B -0.3956 0.7910 0.1050 0.034 Uiso calc R 1 . .
C C11B -0.33334(12) 0.94331(12) 0.12930(8) 0.0286(3) Uani d . 1 . .
H H11B -0.4079 0.9655 0.1188 0.034 Uiso calc R 1 . .
C C12B -0.23241(12) 1.01431(11) 0.15281(7) 0.0236(3) Uani d . 1 . .
H H12B -0.2380 1.0852 0.1587 0.028 Uiso calc R 1 . .
C C13B -0.12244(11) 0.98269(10) 0.16791(7) 0.0181(2) Uani d . 1 . .
H H13B -0.0529 1.0319 0.1833 0.022 Uiso calc R 1 . .
C C14B -0.11529(10) 0.87815(10) 0.16026(7) 0.0176(2) Uani d . 1 . .
C C15B 0.10829(10) 0.90796(9) 0.15678(7) 0.0160(2) Uani d . 1 . .
H H15C 0.1776 0.8734 0.1689 0.019 Uiso calc R 1 . .
H H15D 0.1187 0.9729 0.1880 0.019 Uiso calc R 1 . .
C C16B 0.10798(11) 0.93317(10) 0.07102(7) 0.0191(2) Uani d . 1 . .
H H16C 0.0473 0.9779 0.0615 0.023 Uiso calc R 1 . .
H H16D 0.1884 0.9735 0.0586 0.023 Uiso calc R 1 . .
C C17B 0.08041(11) 0.84068(10) 0.01625(7) 0.0201(3) Uani d . 1 . .
H H17C -0.0022 0.8027 0.0263 0.024 Uiso calc R 1 . .
H H17D 0.0804 0.8658 -0.0375 0.024 Uiso calc R 1 . .
C C18B 0.29610(11) 0.81780(11) 0.01351(8) 0.0245(3) Uani d . 1 . .
H H18D 0.3482 0.7655 0.0146 0.037 Uiso calc R 1 . .
H H18E 0.3199 0.8679 0.0561 0.037 Uiso calc R 1 . .
H H18F 0.3049 0.8536 -0.0359 0.037 Uiso calc R 1 . .
C C19B 0.13262(14) 0.68120(11) -0.03663(8) 0.0293(3) Uani d . 1 . .
H H19D 0.0488 0.6468 -0.0287 0.044 Uiso calc R 1 . .
H H19E 0.1868 0.6310 -0.0311 0.044 Uiso calc R 1 . .
H H19F 0.1396 0.7098 -0.0887 0.044 Uiso calc R 1 . .
O O1C 0.26076(8) 0.70245(7) 0.15382(5) 0.0229(2) Uani d . 1 . .
O O21C 0.38889(9) 0.86117(7) 0.24018(6) 0.0298(2) Uani d . 1 . .
O O22C 0.50236(9) 0.79895(8) 0.32264(7) 0.0370(3) Uani d . 1 . .
O O41C 0.27695(10) 0.55178(8) 0.49309(5) 0.0319(2) Uani d . 1 . .
O O42C 0.12957(9) 0.43593(8) 0.44634(6) 0.0346(3) Uani d . 1 . .
O O61C -0.00593(11) 0.44920(9) 0.18672(7) 0.0511(4) Uani d . 1 . .
O O62C 0.04994(9) 0.58148(9) 0.11703(6) 0.0384(3) Uani d . 1 . .
N N2C 0.41012(9) 0.79142(8) 0.28158(7) 0.0214(2) Uani d . 1 . .
N N4C 0.20810(10) 0.51373(9) 0.43944(6) 0.0229(2) Uani d . 1 . .
N N6C 0.05988(10) 0.53218(9) 0.17559(6) 0.0225(2) Uani d . 1 . .
C C1C 0.24304(10) 0.66219(9) 0.21843(7) 0.0156(2) Uani d . 1 . .
C C2C 0.31920(10) 0.69712(9) 0.28621(7) 0.0161(2) Uani d . 1 . .
C C3C 0.31107(11) 0.64889(9) 0.35594(7) 0.0174(2) Uani d . 1 . .
H H3CA 0.3660 0.6739 0.3974 0.021 Uiso calc R 1 . .
C C4C 0.22078(11) 0.56251(9) 0.36500(7) 0.0171(2) Uani d . 1 . .
C C5C 0.14014(10) 0.52518(10) 0.30518(7) 0.0175(2) Uani d . 1 . .
H H5CA 0.0786 0.4665 0.3126 0.021 Uiso calc R 1 . .
C C6C 0.14961(10) 0.57354(9) 0.23489(7) 0.0168(2) Uani d . 1 . .
O O1D 0.71604(8) 0.69222(7) 0.67815(5) 0.0226(2) Uani d . 1 . .
O O21D 0.52660(10) 0.56347(9) 0.61786(6) 0.0393(3) Uani d . 1 . .
O O22D 0.43317(9) 0.44269(9) 0.68675(6) 0.0362(3) Uani d . 1 . .
O O41D 0.53373(9) 0.39608(8) 0.94767(6) 0.0316(2) Uani d . 1 . .
O O42D 0.68754(10) 0.49588(8) 1.00391(6) 0.0322(2) Uani d . 1 . .
O O61D 0.91601(11) 0.78149(10) 0.86413(8) 0.0555(4) Uani d . 1 . .
O O62D 0.81134(9) 0.84577(8) 0.77794(6) 0.0337(2) Uani d . 1 . .
N N2D 0.51250(9) 0.51864(8) 0.67940(6) 0.0176(2) Uani d . 1 . .
N N4D 0.61854(10) 0.47077(9) 0.94774(6) 0.0232(2) Uani d . 1 . .
N N6D 0.83039(10) 0.77441(9) 0.81814(7) 0.0266(3) Uani d . 1 . .
C C1D 0.68478(10) 0.64639(9) 0.73884(7) 0.0149(2) Uani d . 1 . .
C C2D 0.59071(10) 0.55516(9) 0.74548(7) 0.0152(2) Uani d . 1 . .
C C3D 0.56982(10) 0.49945(9) 0.81231(7) 0.0167(2) Uani d . 1 . .
H H3DA 0.5083 0.4395 0.8129 0.020 Uiso calc R 1 . .
C C4D 0.63868(11) 0.53121(10) 0.87829(7) 0.0176(2) Uani d . 1 . .
C C5D 0.72585(11) 0.62116(10) 0.87969(7) 0.0198(3) Uani d . 1 . .
H H5DA 0.7717 0.6434 0.9256 0.024 Uiso calc R 1 . .
C C6D 0.74406(11) 0.67694(9) 0.81332(7) 0.0175(2) 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 0.0033 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1A N1A C14A . . 114.64(10) ?
C1A N1A C15A . . 116.51(10) ?
C14A N1A C15A . . 116.45(10) ?
C19A N2A C18A . . 110.55(10) ?
C19A N2A C17A . . 110.57(9) ?
C18A N2A C17A . . 112.47(10) ?
C19A N2A H2AB . . 107.7 ?
C18A N2A H2AB . . 107.7 ?
C17A N2A H2AB . . 107.7 ?
C2A C1A C6A . . 120.33(11) ?
C2A C1A N1A . . 122.10(11) ?
C6A C1A N1A . . 117.57(11) ?
C3A C2A C1A . . 119.05(11) ?
C3A C2A H2AA . . 120.5 ?
C1A C2A H2AA . . 120.5 ?
C4A C3A C2A . . 122.16(11) ?
C4A C3A Cl1 . . 118.28(10) ?
C2A C3A Cl1 . . 119.53(10) ?
C3A C4A C5A . . 117.92(11) ?
C3A C4A H4AA . . 121.0 ?
C5A C4A H4AA . . 121.0 ?
C6A C5A C4A . . 121.75(12) ?
C6A C5A H5AA . . 119.1 ?
C4A C5A H5AA . . 119.1 ?
C5A C6A C1A . . 118.74(11) ?
C5A C6A C7A . . 122.46(11) ?
C1A C6A C7A . . 118.80(11) ?
C6A C7A C8A . . 112.37(12) ?
C6A C7A H7AA . . 109.1 ?
C8A C7A H7AA . . 109.1 ?
C6A C7A H7AB . . 109.1 ?
C8A C7A H7AB . . 109.1 ?
H7AA C7A H7AB . . 107.9 ?
C9A C8A C7A . . 118.47(11) ?
C9A C8A H8AA . . 107.7 ?
C7A C8A H8AA . . 107.7 ?
C9A C8A H8AB . . 107.7 ?
C7A C8A H8AB . . 107.7 ?
H8AA C8A H8AB . . 107.1 ?
C10A C9A C14A . . 117.66(12) ?
C10A C9A C8A . . 115.25(12) ?
C14A C9A C8A . . 127.09(12) ?
C11A C10A C9A . . 122.66(13) ?
C11A C10A H10A . . 118.7 ?
C9A C10A H10A . . 118.7 ?
C12A C11A C10A . . 119.06(12) ?
C12A C11A H11A . . 120.5 ?
C10A C11A H11A . . 120.5 ?
C11A C12A C13A . . 119.82(13) ?
C11A C12A H12A . . 120.1 ?
C13A C12A H12A . . 120.1 ?
C12A C13A C14A . . 121.31(12) ?
C12A C13A H13A . . 119.3 ?
C14A C13A H13A . . 119.3 ?
C13A C14A C9A . . 119.45(11) ?
C13A C14A N1A . . 119.22(11) ?
C9A C14A N1A . . 121.33(11) ?
N1A C15A C16A . . 111.90(10) ?
N1A C15A H15A . . 109.2 ?
C16A C15A H15A . . 109.2 ?
N1A C15A H15B . . 109.2 ?
C16A C15A H15B . . 109.2 ?
H15A C15A H15B . . 107.9 ?
C17A C16A C15A . . 110.88(10) ?
C17A C16A H16A . . 109.5 ?
C15A C16A H16A . . 109.5 ?
C17A C16A H16B . . 109.5 ?
C15A C16A H16B . . 109.5 ?
H16A C16A H16B . . 108.1 ?
N2A C17A C16A . . 113.17(10) ?
N2A C17A H17A . . 108.9 ?
C16A C17A H17A . . 108.9 ?
N2A C17A H17B . . 108.9 ?
C16A C17A H17B . . 108.9 ?
H17A C17A H17B . . 107.8 ?
N2A C18A H18A . . 109.5 ?
N2A C18A H18B . . 109.5 ?
H18A C18A H18B . . 109.5 ?
N2A C18A H18C . . 109.5 ?
H18A C18A H18C . . 109.5 ?
H18B C18A H18C . . 109.5 ?
N2A C19A H19A . . 109.5 ?
N2A C19A H19B . . 109.5 ?
H19A C19A H19B . . 109.5 ?
N2A C19A H19C . . 109.5 ?
H19A C19A H19C . . 109.5 ?
H19B C19A H19C . . 109.5 ?
C1B N1B C14B . . 113.91(9) ?
C1B N1B C15B . . 116.48(9) ?
C14B N1B C15B . . 116.06(9) ?
C18B N2B C19B . . 110.68(11) ?
C18B N2B C17B . . 112.88(10) ?
C19B N2B C17B . . 109.41(10) ?
C18B N2B H2BB . . 107.9 ?
C19B N2B H2BB . . 107.9 ?
C17B N2B H2BB . . 107.9 ?
C2B C1B C6B . . 119.35(11) ?
C2B C1B N1B . . 119.55(10) ?
C6B C1B N1B . . 121.08(11) ?
C3B C2B C1B . . 120.54(12) ?
C3B C2B H2BA . . 119.7 ?
C1B C2B H2BA . . 119.7 ?
C4B C3B C2B . . 121.28(13) ?
C4B C3B Cl2 . . 119.96(11) ?
C2B C3B Cl2 . . 118.74(11) ?
C5B C4B C3B . . 117.97(13) ?
C5B C4B H4BA . . 121.0 ?
C3B C4B H4BA . . 121.0 ?
C4B C5B C6B . . 123.43(13) ?
C4B C5B H5BA . . 118.3 ?
C6B C5B H5BA . . 118.3 ?
C5B C6B C1B . . 117.41(13) ?
C5B C6B C7B . . 116.14(12) ?
C1B C6B C7B . . 126.43(12) ?
C6B C7B C8B . . 118.55(11) ?
C6B C7B H7BA . . 107.7 ?
C8B C7B H7BA . . 107.7 ?
C6B C7B H7BB . . 107.7 ?
C8B C7B H7BB . . 107.7 ?
H7BA C7B H7BB . . 107.1 ?
C9B C8B C7B . . 110.77(13) ?
C9B C8B H8BA . . 109.5 ?
C7B C8B H8BA . . 109.5 ?
C9B C8B H8BB . . 109.5 ?
C7B C8B H8BB . . 109.5 ?
H8BA C8B H8BB . . 108.1 ?
C10B C9B C14B . . 118.76(13) ?
C10B C9B C8B . . 122.75(12) ?
C14B C9B C8B . . 118.35(11) ?
C11B C10B C9B . . 120.80(13) ?
C11B C10B H10B . . 119.6 ?
C9B C10B H10B . . 119.6 ?
C12B C11B C10B . . 119.94(12) ?
C12B C11B H11B . . 120.0 ?
C10B C11B H11B . . 120.0 ?
C11B C12B C13B . . 120.47(13) ?
C11B C12B H12B . . 119.8 ?
C13B C12B H12B . . 119.8 ?
C12B C13B C14B . . 119.50(12) ?
C12B C13B H13B . . 120.2 ?
C14B C13B H13B . . 120.2 ?
C13B C14B C9B . . 120.51(11) ?
C13B C14B N1B . . 122.00(11) ?
C9B C14B N1B . . 117.48(11) ?
N1B C15B C16B . . 111.24(9) ?
N1B C15B H15C . . 109.4 ?
C16B C15B H15C . . 109.4 ?
N1B C15B H15D . . 109.4 ?
C16B C15B H15D . . 109.4 ?
H15C C15B H15D . . 108.0 ?
C17B C16B C15B . . 115.30(10) ?
C17B C16B H16C . . 108.4 ?
C15B C16B H16C . . 108.5 ?
C17B C16B H16D . . 108.5 ?
C15B C16B H16D . . 108.4 ?
H16C C16B H16D . . 107.5 ?
N2B C17B C16B . . 114.80(10) ?
N2B C17B H17C . . 108.6 ?
C16B C17B H17C . . 108.6 ?
N2B C17B H17D . . 108.6 ?
C16B C17B H17D . . 108.6 ?
H17C C17B H17D . . 107.5 ?
N2B C18B H18D . . 109.5 ?
N2B C18B H18E . . 109.5 ?
H18D C18B H18E . . 109.5 ?
N2B C18B H18F . . 109.5 ?
H18D C18B H18F . . 109.5 ?
H18E C18B H18F . . 109.5 ?
N2B C19B H19D . . 109.5 ?
N2B C19B H19E . . 109.5 ?
H19D C19B H19E . . 109.5 ?
N2B C19B H19F . . 109.5 ?
H19D C19B H19F . . 109.5 ?
H19E C19B H19F . . 109.5 ?
O21C N2C O22C . . 123.02(10) ?
O21C N2C C2C . . 118.88(10) ?
O22C N2C C2C . . 118.01(10) ?
O42C N4C O41C . . 123.09(11) ?
O42C N4C C4C . . 118.58(11) ?
O41C N4C C4C . . 118.33(11) ?
O61C N6C O62C . . 121.82(11) ?
O61C N6C C6C . . 118.33(11) ?
O62C N6C C6C . . 119.83(10) ?
O1C C1C C2C . . 122.71(10) ?
O1C C1C C6C . . 125.28(11) ?
C2C C1C C6C . . 111.96(10) ?
C3C C2C C1C . . 124.71(11) ?
C3C C2C N2C . . 116.39(10) ?
C1C C2C N2C . . 118.89(10) ?
C2C C3C C4C . . 118.73(11) ?
C2C C3C H3CA . . 120.6 ?
C4C C3C H3CA . . 120.6 ?
C5C C4C C3C . . 121.31(11) ?
C5C C4C N4C . . 119.49(11) ?
C3C C4C N4C . . 119.14(11) ?
C6C C5C C4C . . 119.64(11) ?
C6C C5C H5CA . . 120.2 ?
C4C C5C H5CA . . 120.2 ?
C5C C6C N6C . . 116.65(10) ?
C5C C6C C1C . . 123.51(11) ?
N6C C6C C1C . . 119.84(10) ?
O22D N2D O21D . . 121.40(10) ?
O22D N2D C2D . . 118.52(10) ?
O21D N2D C2D . . 120.08(10) ?
O42D N4D O41D . . 123.15(11) ?
O42D N4D C4D . . 118.23(11) ?
O41D N4D C4D . . 118.62(11) ?
O62D N6D O61D . . 123.40(12) ?
O62D N6D C6D . . 118.39(11) ?
O61D N6D C6D . . 118.16(11) ?
O1D C1D C6D . . 122.60(11) ?
O1D C1D C2D . . 126.13(11) ?
C6D C1D C2D . . 111.22(10) ?
C3D C2D N2D . . 116.41(10) ?
C3D C2D C1D . . 123.81(10) ?
N2D C2D C1D . . 119.79(10) ?
C2D C3D C4D . . 119.71(11) ?
C2D C3D H3DA . . 120.1 ?
C4D C3D H3DA . . 120.1 ?
C3D C4D C5D . . 121.16(11) ?
C3D C4D N4D . . 119.45(11) ?
C5D C4D N4D . . 119.37(11) ?
C6D C5D C4D . . 118.51(11) ?
C6D C5D H5DA . . 120.7 ?
C4D C5D H5DA . . 120.7 ?
C5D C6D C1D . . 125.15(11) ?
C5D C6D N6D . . 117.09(11) ?
C1D C6D N6D . . 117.76(10) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C3A . 1.7427(13) ?
N1A C1A . 1.4329(15) ?
N1A C14A . 1.4441(15) ?
N1A C15A . 1.4656(15) ?
N2A C19A . 1.4879(16) ?
N2A C18A . 1.4879(16) ?
N2A C17A . 1.4940(15) ?
N2A H2AB . 0.9300 ?
C1A C2A . 1.3912(17) ?
C1A C6A . 1.4050(17) ?
C2A C3A . 1.3870(17) ?
C2A H2AA . 0.9500 ?
C3A C4A . 1.3841(18) ?
C4A C5A . 1.3950(18) ?
C4A H4AA . 0.9500 ?
C5A C6A . 1.3890(17) ?
C5A H5AA . 0.9500 ?
C6A C7A . 1.5019(17) ?
C7A C8A . 1.5214(19) ?
C7A H7AA . 0.9900 ?
C7A H7AB . 0.9900 ?
C8A C9A . 1.5145(19) ?
C8A H8AA . 0.9900 ?
C8A H8AB . 0.9900 ?
C9A C10A . 1.3983(19) ?
C9A C14A . 1.4043(17) ?
C10A C11A . 1.387(2) ?
C10A H10A . 0.9500 ?
C11A C12A . 1.3765(19) ?
C11A H11A . 0.9500 ?
C12A C13A . 1.3887(18) ?
C12A H12A . 0.9500 ?
C13A C14A . 1.3984(18) ?
C13A H13A . 0.9500 ?
C15A C16A . 1.5273(17) ?
C15A H15A . 0.9900 ?
C15A H15B . 0.9900 ?
C16A C17A . 1.5182(18) ?
C16A H16A . 0.9900 ?
C16A H16B . 0.9900 ?
C17A H17A . 0.9900 ?
C17A H17B . 0.9900 ?
C18A H18A . 0.9800 ?
C18A H18B . 0.9800 ?
C18A H18C . 0.9800 ?
C19A H19A . 0.9800 ?
C19A H19B . 0.9800 ?
C19A H19C . 0.9800 ?
Cl2 C3B . 1.7459(15) ?
N1B C1B . 1.4240(15) ?
N1B C14B . 1.4435(15) ?
N1B C15B . 1.4692(14) ?
N2B C18B . 1.4920(16) ?
N2B C19B . 1.4950(17) ?
N2B C17B . 1.5016(16) ?
N2B H2BB . 0.9300 ?
C1B C2B . 1.4004(17) ?
C1B C6B . 1.4150(17) ?
C2B C3B . 1.3864(17) ?
C2B H2BA . 0.9500 ?
C3B C4B . 1.381(2) ?
C4B C5B . 1.379(2) ?
C4B H4BA . 0.9500 ?
C5B C6B . 1.402(2) ?
C5B H5BA . 0.9500 ?
C6B C7B . 1.515(2) ?
C7B C8B . 1.528(2) ?
C7B H7BA . 0.9900 ?
C7B H7BB . 0.9900 ?
C8B C9B . 1.496(2) ?
C8B H8BA . 0.9900 ?
C8B H8BB . 0.9900 ?
C9B C10B . 1.3979(18) ?
C9B C14B . 1.3985(17) ?
C10B C11B . 1.387(2) ?
C10B H10B . 0.9500 ?
C11B C12B . 1.381(2) ?
C11B H11B . 0.9500 ?
C12B C13B . 1.3935(17) ?
C12B H12B . 0.9500 ?
C13B C14B . 1.3959(18) ?
C13B H13B . 0.9500 ?
C15B C16B . 1.5238(17) ?
C15B H15C . 0.9900 ?
C15B H15D . 0.9900 ?
C16B C17B . 1.5117(19) ?
C16B H16C . 0.9900 ?
C16B H16D . 0.9900 ?
C17B H17C . 0.9900 ?
C17B H17D . 0.9900 ?
C18B H18D . 0.9800 ?
C18B H18E . 0.9800 ?
C18B H18F . 0.9800 ?
C19B H19D . 0.9800 ?
C19B H19E . 0.9800 ?
C19B H19F . 0.9800 ?
O1C C1C . 1.2474(14) ?
O21C N2C . 1.2265(13) ?
O22C N2C . 1.2316(13) ?
O41C N4C . 1.2343(14) ?
O42C N4C . 1.2326(14) ?
O61C N6C . 1.2221(14) ?
O62C N6C . 1.2248(14) ?
N2C C2C . 1.4606(15) ?
N4C C4C . 1.4447(15) ?
N6C C6C . 1.4501(15) ?
C1C C2C . 1.4540(16) ?
C1C C6C . 1.4558(16) ?
C2C C3C . 1.3678(17) ?
C3C C4C . 1.3917(17) ?
C3C H3CA . 0.9500 ?
C4C C5C . 1.3836(16) ?
C5C C6C . 1.3773(16) ?
C5C H5CA . 0.9500 ?
O1D C1D . 1.2429(14) ?
O21D N2D . 1.2234(13) ?
O22D N2D . 1.2218(13) ?
O41D N4D . 1.2377(14) ?
O42D N4D . 1.2323(14) ?
O61D N6D . 1.2244(14) ?
O62D N6D . 1.2236(15) ?
N2D C2D . 1.4474(14) ?
N4D C4D . 1.4491(15) ?
N6D C6D . 1.4602(16) ?
C1D C6D . 1.4534(16) ?
C1D C2D . 1.4552(16) ?
C2D C3D . 1.3789(16) ?
C3D C4D . 1.3800(17) ?
C3D H3DA . 0.9500 ?
C4D C5D . 1.3913(18) ?
C5D C6D . 1.3703(17) ?
C5D H5DA . 0.9500 ?
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
N2A H2AB O1D . 0.93 1.85 2.7000(13) 150.6
N2A H2AB O21D . 0.93 2.23 2.8982(14) 128.4
N2B H2BB O1C . 0.93 1.92 2.6970(13) 139.6
N2B H2BB O62C . 0.93 2.36 3.0657(15) 133.0
C12A H12A <i>Cg</i>7 1_545 0.95 2.83 3.656(4) 145
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C14A N1A C1A C2A . . . . -107.63(13) ?
C15A N1A C1A C2A . . . . 33.30(16) ?
C14A N1A C1A C6A . . . . 72.36(14) ?
C15A N1A C1A C6A . . . . -146.71(11) ?
C6A C1A C2A C3A . . . . -1.34(18) ?
N1A C1A C2A C3A . . . . 178.65(11) ?
C1A C2A C3A C4A . . . . -0.64(19) ?
C1A C2A C3A Cl1 . . . . -178.58(9) ?
C2A C3A C4A C5A . . . . 1.07(18) ?
Cl1 C3A C4A C5A . . . . 179.03(9) ?
C3A C4A C5A C6A . . . . 0.48(19) ?
C4A C5A C6A C1A . . . . -2.38(19) ?
C4A C5A C6A C7A . . . . 177.53(12) ?
C2A C1A C6A C5A . . . . 2.80(18) ?
N1A C1A C6A C5A . . . . -177.19(11) ?
C2A C1A C6A C7A . . . . -177.11(11) ?
N1A C1A C6A C7A . . . . 2.90(17) ?
C5A C6A C7A C8A . . . . 108.32(14) ?
C1A C6A C7A C8A . . . . -71.77(15) ?
C6A C7A C8A C9A . . . . 53.41(17) ?
C7A C8A C9A C10A . . . . -178.17(13) ?
C7A C8A C9A C14A . . . . 1.9(2) ?
C14A C9A C10A C11A . . . . 1.1(2) ?
C8A C9A C10A C11A . . . . -178.89(13) ?
C9A C10A C11A C12A . . . . -1.9(2) ?
C10A C11A C12A C13A . . . . 0.9(2) ?
C11A C12A C13A C14A . . . . 0.7(2) ?
C12A C13A C14A C9A . . . . -1.53(19) ?
C12A C13A C14A N1A . . . . 179.06(11) ?
C10A C9A C14A C13A . . . . 0.63(18) ?
C8A C9A C14A C13A . . . . -179.43(13) ?
C10A C9A C14A N1A . . . . -179.98(12) ?
C8A C9A C14A N1A . . . . 0.0(2) ?
C1A N1A C14A C13A . . . . 119.29(12) ?
C15A N1A C14A C13A . . . . -21.67(16) ?
C1A N1A C14A C9A . . . . -60.10(15) ?
C15A N1A C14A C9A . . . . 158.94(11) ?
C1A N1A C15A C16A . . . . 59.19(14) ?
C14A N1A C15A C16A . . . . -160.59(10) ?
N1A C15A C16A C17A . . . . 63.99(13) ?
C19A N2A C17A C16A . . . . -178.29(10) ?
C18A N2A C17A C16A . . . . -54.17(13) ?
C15A C16A C17A N2A . . . . -168.79(10) ?
C14B N1B C1B C2B . . . . -122.02(12) ?
C15B N1B C1B C2B . . . . 17.24(16) ?
C14B N1B C1B C6B . . . . 56.77(16) ?
C15B N1B C1B C6B . . . . -163.97(11) ?
C6B C1B C2B C3B . . . . -1.29(18) ?
N1B C1B C2B C3B . . . . 177.51(11) ?
C1B C2B C3B C4B . . . . 0.2(2) ?
C1B C2B C3B Cl2 . . . . -178.11(9) ?
C2B C3B C4B C5B . . . . 0.6(2) ?
Cl2 C3B C4B C5B . . . . 178.84(10) ?
C3B C4B C5B C6B . . . . -0.2(2) ?
C4B C5B C6B C1B . . . . -0.9(2) ?
C4B C5B C6B C7B . . . . 177.65(13) ?
C2B C1B C6B C5B . . . . 1.62(18) ?
N1B C1B C6B C5B . . . . -177.17(11) ?
C2B C1B C6B C7B . . . . -176.77(13) ?
N1B C1B C6B C7B . . . . 4.4(2) ?
C5B C6B C7B C8B . . . . 179.37(13) ?
C1B C6B C7B C8B . . . . -2.2(2) ?
C6B C7B C8B C9B . . . . -56.27(17) ?
C7B C8B C9B C10B . . . . -105.22(15) ?
C7B C8B C9B C14B . . . . 70.35(16) ?
C14B C9B C10B C11B . . . . 0.6(2) ?
C8B C9B C10B C11B . . . . 176.18(14) ?
C9B C10B C11B C12B . . . . -0.2(2) ?
C10B C11B C12B C13B . . . . 0.4(2) ?
C11B C12B C13B C14B . . . . -0.99(19) ?
C12B C13B C14B C9B . . . . 1.41(19) ?
C12B C13B C14B N1B . . . . -177.79(11) ?
C10B C9B C14B C13B . . . . -1.22(19) ?
C8B C9B C14B C13B . . . . -176.97(12) ?
C10B C9B C14B N1B . . . . 178.02(11) ?
C8B C9B C14B N1B . . . . 2.26(18) ?
C1B N1B C14B C13B . . . . 102.50(13) ?
C15B N1B C14B C13B . . . . -36.93(16) ?
C1B N1B C14B C9B . . . . -76.72(14) ?
C15B N1B C14B C9B . . . . 143.84(12) ?
C1B N1B C15B C16B . . . . 165.18(10) ?
C14B N1B C15B C16B . . . . -56.43(14) ?
N1B C15B C16B C17B . . . . -53.28(14) ?
C18B N2B C17B C16B . . . . -54.25(14) ?
C19B N2B C17B C16B . . . . -177.97(11) ?
C15B C16B C17B N2B . . . . -59.81(14) ?
O1C C1C C2C C3C . . . . -172.94(12) ?
C6C C1C C2C C3C . . . . 4.51(17) ?
O1C C1C C2C N2C . . . . 8.32(18) ?
C6C C1C C2C N2C . . . . -174.22(10) ?
O21C N2C C2C C3C . . . . -146.36(12) ?
O22C N2C C2C C3C . . . . 30.17(17) ?
O21C N2C C2C C1C . . . . 32.47(17) ?
O22C N2C C2C C1C . . . . -151.00(12) ?
C1C C2C C3C C4C . . . . -2.84(19) ?
N2C C2C C3C C4C . . . . 175.92(11) ?
C2C C3C C4C C5C . . . . 0.02(18) ?
C2C C3C C4C N4C . . . . -177.33(11) ?
O42C N4C C4C C5C . . . . 4.18(18) ?
O41C N4C C4C C5C . . . . -176.14(11) ?
O42C N4C C4C C3C . . . . -178.43(11) ?
O41C N4C C4C C3C . . . . 1.26(17) ?
C3C C4C C5C C6C . . . . 0.60(18) ?
N4C C4C C5C C6C . . . . 177.94(11) ?
C4C C5C C6C N6C . . . . -178.20(11) ?
C4C C5C C6C C1C . . . . 1.51(19) ?
O61C N6C C6C C5C . . . . -10.99(18) ?
O62C N6C C6C C5C . . . . 167.41(12) ?
O61C N6C C6C C1C . . . . 169.29(13) ?
O62C N6C C6C C1C . . . . -12.31(18) ?
O1C C1C C6C C5C . . . . 173.58(12) ?
C2C C1C C6C C5C . . . . -3.79(17) ?
O1C C1C C6C N6C . . . . -6.71(19) ?
C2C C1C C6C N6C . . . . 175.92(10) ?
O22D N2D C2D C3D . . . . 0.77(16) ?
O21D N2D C2D C3D . . . . -179.14(12) ?
O22D N2D C2D C1D . . . . -179.04(11) ?
O21D N2D C2D C1D . . . . 1.04(17) ?
O1D C1D C2D C3D . . . . 171.41(12) ?
C6D C1D C2D C3D . . . . -6.16(16) ?
O1D C1D C2D N2D . . . . -8.79(18) ?
C6D C1D C2D N2D . . . . 173.63(10) ?
N2D C2D C3D C4D . . . . -178.30(11) ?
C1D C2D C3D C4D . . . . 1.50(18) ?
C2D C3D C4D C5D . . . . 2.70(18) ?
C2D C3D C4D N4D . . . . -178.33(11) ?
O42D N4D C4D C3D . . . . 174.21(11) ?
O41D N4D C4D C3D . . . . -5.20(17) ?
O42D N4D C4D C5D . . . . -6.80(17) ?
O41D N4D C4D C5D . . . . 173.79(12) ?
C3D C4D C5D C6D . . . . -1.40(19) ?
N4D C4D C5D C6D . . . . 179.63(11) ?
C4D C5D C6D C1D . . . . -4.27(19) ?
C4D C5D C6D N6D . . . . 176.05(11) ?
O1D C1D C6D C5D . . . . -170.03(12) ?
C2D C1D C6D C5D . . . . 7.64(17) ?
O1D C1D C6D N6D . . . . 9.64(18) ?
C2D C1D C6D N6D . . . . -172.68(10) ?
O62D N6D C6D C5D . . . . -146.57(13) ?
O61D N6D C6D C5D . . . . 31.08(19) ?
O62D N6D C6D C1D . . . . 33.73(18) ?
O61D N6D C6D C1D . . . . -148.62(14) ?
