#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:56:18 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178412 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/33/4023385.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_4023385
loop_
_publ_author_name
'Balwinder S. Bhatti'
'Jon-Paul Strachan'
'Scott R. Breining'
'Craig H. Miller'
'Persida Tahiri'
'Peter A. Crooks'
'Niranjan Deo'
'Cynthia S. Day'
'William S. Caldwell'
_publ_section_title
;
 Synthesis of 2-(Pyridin-3-yl)-1-azabicyclo[3.2.2]nonane,
 2-(Pyridin-3-yl)-1-azabicyclo[2.2.2]octane, and
 2-(Pyridin-3-yl)-1-azabicyclo[3.2.1]octane,
 a Class of Potent Nicotinic Acetylcholine Receptor--Ligands
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3497
_journal_page_last               3507
_journal_paper_doi               10.1021/jo800028q
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C26 H42 Cl4 N4 O'
_chemical_formula_weight         568.44
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           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           SHELXTL-PC
_cell_angle_alpha                101.897(12)
_cell_angle_beta                 92.696(14)
_cell_angle_gamma                98.098(10)
_cell_formula_units_Z            1
_cell_length_a                   6.7509(9)
_cell_length_b                   9.4347(16)
_cell_length_c                   11.7308(16)
_cell_measurement_reflns_used    45
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      12.53
_cell_measurement_theta_min      3.58
_cell_volume                     721.59(18)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.919
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_device_type  'Bruker P4 1.0mm pinhole'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3796
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.54
_diffrn_standards_interval_count 397
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.436
_exptl_absorpt_correction_T_max  0.9536
_exptl_absorpt_correction_T_min  0.7798
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             302
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.23(9)
_refine_ls_extinction_coef       0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         3796
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0563P)²+0.1041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1195
_reflns_number_gt                2717
_reflns_number_total             3796
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800028q-File001_4.cif
_cod_data_source_block           targ3-1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4023385
loop_
_symmetry_equiv_pos_as_xyz
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.1552(3) -0.15456(19) -0.34995(15) 0.0665(6) Uani 1 1 d . . .
Cl2 Cl -0.2305(2) -0.05607(14) -0.75940(11) 0.0434(4) Uani 1 1 d . . .
Cl3 Cl -0.9498(3) 0.31981(19) -0.37819(15) 0.0614(5) Uani 1 1 d . . .
Cl4 Cl -0.89204(19) 0.22294(14) 0.04564(11) 0.0419(4) Uani 1 1 d . . .
C1 C -0.5178(9) 0.1569(7) -0.5664(5) 0.0358(14) Uani 1 1 d . . .
C2 C -0.4005(10) 0.0855(7) -0.5041(5) 0.0425(15) Uani 1 1 d . . .
H2 H -0.2673 0.1263 -0.4815 0.051 Uiso 1 1 calc R . .
N3 N -0.4747(9) -0.0425(7) -0.4752(5) 0.0507(14) Uani 1 1 d . . .
H3 H -0.3973 -0.0855 -0.4379 0.061 Uiso 1 1 calc R . .
C4 C -0.6667(12) -0.1025(8) -0.5039(6) 0.0539(19) Uani 1 1 d . . .
H4 H -0.7159 -0.1895 -0.4822 0.065 Uiso 1 1 calc R . .
C5 C -0.7911(11) -0.0374(8) -0.5646(6) 0.0495(17) Uani 1 1 d . . .
H5 H -0.9247 -0.0788 -0.5848 0.059 Uiso 1 1 calc R . .
C6 C -0.7132(10) 0.0919(8) -0.5953(6) 0.0443(16) Uani 1 1 d . . .
H6 H -0.7969 0.1365 -0.6373 0.053 Uiso 1 1 calc R . .
C7 C -0.4222(8) 0.2997(6) -0.5923(4) 0.0376(12) Uani 1 1 d . . .
H7 H -0.3308 0.3512 -0.5244 0.045 Uiso 1 1 calc R . .
N8 N -0.2959(7) 0.2661(5) -0.6957(4) 0.0379(12) Uani 1 1 d . . .
H8 H -0.2719 0.1726 -0.7003 0.045 Uiso 1 1 calc R . .
C9 C -0.3911(11) 0.2694(7) -0.8137(5) 0.0514(17) Uani 1 1 d . . .
H9A H -0.5320 0.2279 -0.8194 0.062 Uiso 1 1 calc R . .
H9B H -0.3270 0.2097 -0.8742 0.062 Uiso 1 1 calc R . .
C10 C -0.3718(13) 0.4256(8) -0.8335(6) 0.062(2) Uani 1 1 d . . .
H10A H -0.2736 0.4372 -0.8900 0.075 Uiso 1 1 calc R . .
H10B H -0.4996 0.4406 -0.8666 0.075 Uiso 1 1 calc R . .
C11 C -0.3088(12) 0.5435(9) -0.7218(7) 0.058(2) Uani 1 1 d . . .
H11 H -0.2868 0.6388 -0.7438 0.070 Uiso 1 1 calc R . .
C12 C -0.1086(13) 0.5180(10) -0.6691(9) 0.077(3) Uani 1 1 d . . .
H12A H -0.0010 0.5590 -0.7102 0.092 Uiso 1 1 calc R . .
H12B H -0.0890 0.5702 -0.5880 0.092 Uiso 1 1 calc R . .
C13 C -0.0947(10) 0.3610(8) -0.6746(5) 0.0498(18) Uani 1 1 d . . .
H13A H -0.0297 0.3514 -0.6017 0.060 Uiso 1 1 calc R . .
H13B H -0.0118 0.3272 -0.7368 0.060 Uiso 1 1 calc R . .
C14 C -0.5700(9) 0.4017(7) -0.6134(6) 0.0542(15) Uani 1 1 d . . .
H14A H -0.6595 0.3537 -0.6818 0.065 Uiso 1 1 calc R . .
H14B H -0.6510 0.4176 -0.5471 0.065 Uiso 1 1 calc R . .
C15 C -0.4715(12) 0.5490(8) -0.6313(7) 0.061(2) Uani 1 1 d . . .
H15A H -0.4099 0.6065 -0.5566 0.073 Uiso 1 1 calc R . .
H15B H -0.5752 0.5999 -0.6565 0.073 Uiso 1 1 calc R . .
C21 C -0.5716(10) 0.0210(7) -0.1325(5) 0.0385(15) Uani 1 1 d . . .
C22 C -0.7170(11) 0.0655(8) -0.1979(5) 0.0487(18) Uani 1 1 d . . .
H22 H -0.8470 0.0140 -0.2106 0.058 Uiso 1 1 calc R . .
N23 N -0.6679(9) 0.1833(6) -0.2426(4) 0.0462(14) Uani 1 1 d . . .
H23 H -0.7602 0.2098 -0.2830 0.055 Uiso 1 1 calc R . .
C24 C -0.4869(13) 0.2625(8) -0.2292(6) 0.0521(18) Uani 1 1 d . . .
H24 H -0.4620 0.3447 -0.2615 0.063 Uiso 1 1 calc R . .
C25 C -0.3385(12) 0.2213(9) -0.1673(6) 0.057(2) Uani 1 1 d . . .
H25 H -0.2097 0.2743 -0.1583 0.069 Uiso 1 1 calc R . .
C26 C -0.3788(10) 0.0997(8) -0.1173(6) 0.0477(17) Uani 1 1 d . . .
H26 H -0.2778 0.0716 -0.0741 0.057 Uiso 1 1 calc R . .
C27 C -0.6212(9) -0.1109(6) -0.0748(5) 0.0411(12) Uani 1 1 d . . .
H27 H -0.5028 -0.1124 -0.0236 0.049 Uiso 1 1 calc R . .
N28 N -0.7942(8) -0.0898(6) 0.0035(4) 0.0387(12) Uani 1 1 d . . .
H28 H -0.8050 0.0072 0.0169 0.046 Uiso 1 1 calc R . .
C29 C -0.7476(11) -0.1229(7) 0.1185(5) 0.0483(16) Uani 1 1 d . . .
H29A H -0.8547 -0.1011 0.1685 0.058 Uiso 1 1 calc R . .
H29B H -0.6245 -0.0611 0.1551 0.058 Uiso 1 1 calc R . .
C30 C -0.7232(14) -0.2849(9) 0.1065(7) 0.066(2) Uani 1 1 d . . .
H30A H -0.5813 -0.2919 0.1136 0.080 Uiso 1 1 calc R . .
H30B H -0.7847 -0.3211 0.1701 0.080 Uiso 1 1 calc R . .
C31 C -0.8155(14) -0.3808(9) -0.0076(7) 0.068(2) Uani 1 1 d . . .
H31 H -0.8469 -0.4807 0.0053 0.082 Uiso 1 1 calc R . .
C32 C -1.0151(12) -0.3331(9) -0.0394(8) 0.068(2) Uani 1 1 d . . .
H32A H -1.0700 -0.3915 -0.1151 0.081 Uiso 1 1 calc R . .
H32B H -1.1090 -0.3532 0.0175 0.081 Uiso 1 1 calc R . .
C33 C -0.9970(10) -0.1715(7) -0.0434(6) 0.0472(16) Uani 1 1 d . . .
H33A H -1.0221 -0.1627 -0.1236 0.057 Uiso 1 1 calc R . .
H33B H -1.0981 -0.1281 0.0020 0.057 Uiso 1 1 calc R . .
C34 C -0.6562(12) -0.2541(7) -0.1621(6) 0.0671(18) Uani 1 1 d . . .
H34A H -0.5427 -0.2598 -0.2096 0.081 Uiso 1 1 calc R . .
H34B H -0.7744 -0.2571 -0.2133 0.081 Uiso 1 1 calc R . .
C35 C -0.6849(15) -0.3873(9) -0.1059(8) 0.080(3) Uani 1 1 d . . .
H35A H -0.7398 -0.4725 -0.1662 0.096 Uiso 1 1 calc R . .
H35B H -0.5537 -0.4029 -0.0782 0.096 Uiso 1 1 calc R . .
O1 O -0.2752(9) -0.4761(6) -0.3197(5) 0.0886(16) Uani 1 1 d D . .
H1A H -0.204(11) -0.436(8) -0.366(6) 0.106 Uiso 1 1 d D . .
H1B H -0.404(3) -0.485(10) -0.329(8) 0.106 Uiso 1 1 d 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 0.0000 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 116.1(6) . . ?
C6 C1 C7 126.3(5) . . ?
C2 C1 C7 117.5(5) . . ?
N3 C2 C1 121.7(6) . . ?
N3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C4 N3 C2 120.8(7) . . ?
C4 N3 H3 119.6 . . ?
C2 N3 H3 119.6 . . ?
N3 C4 C5 120.6(7) . . ?
N3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 118.2(7) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C1 C6 C5 122.7(7) . . ?
C1 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C1 C7 N8 108.4(5) . . ?
C1 C7 C14 114.5(5) . . ?
N8 C7 C14 111.2(4) . . ?
C1 C7 H7 107.5 . . ?
N8 C7 H7 107.5 . . ?
C14 C7 H7 107.5 . . ?
C13 N8 C9 109.7(5) . . ?
C13 N8 C7 111.5(5) . . ?
C9 N8 C7 116.6(5) . . ?
C13 N8 H8 106.1 . . ?
C9 N8 H8 106.1 . . ?
C7 N8 H8 106.1 . . ?
N8 C9 C10 111.4(5) . . ?
N8 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
N8 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C9 113.5(6) . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 C12 108.6(7) . . ?
C10 C11 C15 113.1(7) . . ?
C12 C11 C15 111.6(7) . . ?
C10 C11 H11 107.8 . . ?
C12 C11 H11 107.8 . . ?
C15 C11 H11 107.8 . . ?
C13 C12 C11 113.8(6) . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 N8 112.5(6) . . ?
C12 C13 H13A 109.1 . . ?
N8 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
N8 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C7 114.0(5) . . ?
C15 C14 H14A 108.7 . . ?
C7 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C7 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 C11 115.5(6) . . ?
C14 C15 H15A 108.4 . . ?
C11 C15 H15A 108.4 . . ?
C14 C15 H15B 108.4 . . ?
C11 C15 H15B 108.4 . . ?
H15A C15 H15B 107.5 . . ?
C26 C21 C22 118.7(6) . . ?
C26 C21 C27 120.1(6) . . ?
C22 C21 C27 121.2(6) . . ?
N23 C22 C21 118.8(6) . . ?
N23 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?
C24 N23 C22 124.5(6) . . ?
C24 N23 H23 117.7 . . ?
C22 N23 H23 117.7 . . ?
N23 C24 C25 118.7(6) . . ?
N23 C24 H24 120.7 . . ?
C25 C24 H24 120.7 . . ?
C24 C25 C26 120.1(7) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C21 C26 C25 119.2(7) . . ?
C21 C26 H26 120.4 . . ?
C25 C26 H26 120.4 . . ?
C34 C27 N28 113.0(5) . . ?
C34 C27 C21 112.4(5) . . ?
N28 C27 C21 110.6(4) . . ?
C34 C27 H27 106.8 . . ?
N28 C27 H27 106.8 . . ?
C21 C27 H27 106.8 . . ?
C29 N28 C33 108.1(5) . . ?
C29 N28 C27 111.1(5) . . ?
C33 N28 C27 117.4(5) . . ?
C29 N28 H28 106.5 . . ?
C33 N28 H28 106.5 . . ?
C27 N28 H28 106.5 . . ?
N28 C29 C30 111.2(6) . . ?
N28 C29 H29A 109.4 . . ?
C30 C29 H29A 109.4 . . ?
N28 C29 H29B 109.4 . . ?
C30 C29 H29B 109.4 . . ?
H29A C29 H29B 108.0 . . ?
C31 C30 C29 113.3(6) . . ?
C31 C30 H30A 108.9 . . ?
C29 C30 H30A 108.9 . . ?
C31 C30 H30B 108.9 . . ?
C29 C30 H30B 108.9 . . ?
H30A C30 H30B 107.7 . . ?
C35 C31 C30 115.1(8) . . ?
C35 C31 C32 110.8(7) . . ?
C30 C31 C32 109.2(8) . . ?
C35 C31 H31 107.1 . . ?
C30 C31 H31 107.1 . . ?
C32 C31 H31 107.1 . . ?
C33 C32 C31 113.8(6) . . ?
C33 C32 H32A 108.8 . . ?
C31 C32 H32A 108.8 . . ?
C33 C32 H32B 108.8 . . ?
C31 C32 H32B 108.8 . . ?
H32A C32 H32B 107.7 . . ?
N28 C33 C32 111.7(6) . . ?
N28 C33 H33A 109.3 . . ?
C32 C33 H33A 109.3 . . ?
N28 C33 H33B 109.3 . . ?
C32 C33 H33B 109.3 . . ?
H33A C33 H33B 107.9 . . ?
C27 C34 C35 113.3(6) . . ?
C27 C34 H34A 108.9 . . ?
C35 C34 H34A 108.9 . . ?
C27 C34 H34B 108.9 . . ?
C35 C34 H34B 108.9 . . ?
H34A C34 H34B 107.7 . . ?
C31 C35 C34 117.0(7) . . ?
C31 C35 H35A 108.0 . . ?
C34 C35 H35A 108.0 . . ?
C31 C35 H35B 108.0 . . ?
C34 C35 H35B 108.0 . . ?
H35A C35 H35B 107.3 . . ?
H1A O1 H1B 119(8) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.369(8) . ?
C1 C2 1.383(9) . ?
C1 C7 1.506(8) . ?
C2 N3 1.356(8) . ?
C2 H2 0.9300 . ?
N3 C4 1.337(9) . ?
N3 H3 0.8600 . ?
C4 C5 1.364(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(9) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N8 1.521(7) . ?
C7 C14 1.526(7) . ?
C7 H7 0.9800 . ?
N8 C13 1.498(8) . ?
N8 C9 1.507(7) . ?
N8 H8 0.9100 . ?
C9 C10 1.527(9) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.533(10) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.530(11) . ?
C11 C15 1.561(11) . ?
C11 H11 0.9800 . ?
C12 C13 1.485(12) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.514(9) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C21 C26 1.389(9) . ?
C21 C22 1.381(9) . ?
C21 C27 1.540(8) . ?
C22 N23 1.332(8) . ?
C22 H22 0.9300 . ?
N23 C24 1.324(9) . ?
N23 H23 0.8600 . ?
C24 C25 1.356(10) . ?
C24 H24 0.9300 . ?
C25 C26 1.392(10) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C34 1.499(8) . ?
C27 N28 1.529(7) . ?
C27 H27 0.9800 . ?
N28 C29 1.476(7) . ?
N28 C33 1.493(8) . ?
N28 H28 0.9100 . ?
C29 C30 1.539(10) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.503(10) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C35 1.481(11) . ?
C31 C32 1.533(12) . ?
C31 H31 0.9800 . ?
C32 C33 1.523(10) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.529(10) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
O1 H1A 0.85(2) . ?
O1 H1B 0.86(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 Cl1 0.86 2.14 2.985(6) 167.4 .
N8 H8 Cl2 0.91 2.19 3.076(5) 165.2 .
N23 H23 Cl3 0.86 2.16 3.010(6) 167.9 .
N28 H28 Cl4 0.91 2.16 3.061(6) 169.0 .
O1 H1A Cl1 0.85(2) 2.59(7) 3.125(6) 121(7) .
O1 H1A Cl3 0.85(2) 3.05(8) 3.129(6) 88(6) 1_645
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 N3 1.0(9) . . . . ?
C7 C1 C2 N3 178.9(6) . . . . ?
C1 C2 N3 C4 -1.6(10) . . . . ?
C2 N3 C4 C5 1.1(11) . . . . ?
N3 C4 C5 C6 -0.1(11) . . . . ?
C2 C1 C6 C5 0.1(9) . . . . ?
C7 C1 C6 C5 -177.7(7) . . . . ?
C4 C5 C6 C1 -0.5(11) . . . . ?
C6 C1 C7 N8 -102.7(7) . . . . ?
C2 C1 C7 N8 79.5(6) . . . . ?
C6 C1 C7 C14 22.0(8) . . . . ?
C2 C1 C7 C14 -155.7(6) . . . . ?
C1 C7 N8 C13 -135.0(5) . . . . ?
C14 C7 N8 C13 98.3(6) . . . . ?
C1 C7 N8 C9 98.0(6) . . . . ?
C14 C7 N8 C9 -28.7(7) . . . . ?
C13 N8 C9 C10 -45.5(8) . . . . ?
C7 N8 C9 C10 82.4(7) . . . . ?
N8 C9 C10 C11 -13.9(10) . . . . ?
C9 C10 C11 C12 57.8(9) . . . . ?
C9 C10 C11 C15 -66.6(9) . . . . ?
C10 C11 C12 C13 -40.6(10) . . . . ?
C15 C11 C12 C13 84.7(9) . . . . ?
C11 C12 C13 N8 -17.7(10) . . . . ?
C9 N8 C13 C12 63.8(7) . . . . ?
C7 N8 C13 C12 -66.9(7) . . . . ?
C1 C7 C14 C15 176.1(6) . . . . ?
N8 C7 C14 C15 -60.6(7) . . . . ?
C7 C14 C15 C11 49.1(9) . . . . ?
C10 C11 C15 C14 43.7(9) . . . . ?
C12 C11 C15 C14 -79.1(9) . . . . ?
C26 C21 C22 N23 -0.9(10) . . . . ?
C27 C21 C22 N23 177.7(6) . . . . ?
C21 C22 N23 C24 0.2(10) . . . . ?
C22 N23 C24 C25 1.0(11) . . . . ?
N23 C24 C25 C26 -1.3(12) . . . . ?
C22 C21 C26 C25 0.6(11) . . . . ?
C27 C21 C26 C25 -178.1(6) . . . . ?
C24 C25 C26 C21 0.6(12) . . . . ?
C26 C21 C27 C34 -109.4(7) . . . . ?
C22 C21 C27 C34 72.0(8) . . . . ?
C26 C21 C27 N28 123.2(6) . . . . ?
C22 C21 C27 N28 -55.4(8) . . . . ?
C34 C27 N28 C29 100.1(6) . . . . ?
C21 C27 N28 C29 -132.8(5) . . . . ?
C34 C27 N28 C33 -25.0(7) . . . . ?
C21 C27 N28 C33 102.0(6) . . . . ?
C33 N28 C29 C30 66.5(7) . . . . ?
C27 N28 C29 C30 -63.7(7) . . . . ?
N28 C29 C30 C31 -18.9(10) . . . . ?
C29 C30 C31 C35 85.8(9) . . . . ?
C29 C30 C31 C32 -39.7(9) . . . . ?
C35 C31 C32 C33 -72.6(9) . . . . ?
C30 C31 C32 C33 55.2(9) . . . . ?
C29 N28 C33 C32 -50.7(8) . . . . ?
C27 N28 C33 C32 75.9(7) . . . . ?
C31 C32 C33 N28 -9.3(9) . . . . ?
N28 C27 C34 C35 -59.7(8) . . . . ?
C21 C27 C34 C35 174.3(6) . . . . ?
C30 C31 C35 C34 -75.4(10) . . . . ?
C32 C31 C35 C34 49.2(10) . . . . ?
C27 C34 C35 C31 43.6(11) . . . . ?
