#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:56:18 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178412 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/33/4023383.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_4023383
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                101.987(13)
_cell_angle_beta                 92.628(13)
_cell_angle_gamma                98.121(12)
_cell_formula_units_Z            1
_cell_length_a                   6.7371(9)
_cell_length_b                   9.4204(17)
_cell_length_c                   11.7209(15)
_cell_measurement_reflns_used    54
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      12.55
_cell_measurement_theta_min      3.59
_cell_volume                     718.19(19)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker P4 1.0mm pinhole'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-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    0.0385
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4119
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.54
_diffrn_standards_interval_count 397
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.438
_exptl_absorpt_correction_T_max  0.9253
_exptl_absorpt_correction_T_min  0.7070
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             302
_exptl_crystal_size_max          0.85
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.234
_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   0.01(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         4119
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0551P)²+0.0811P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1081
_reflns_number_gt                3050
_reflns_number_total             4119
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800028q-File001_2.cif
_cod_data_source_block           targ4-1
_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               4023383
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 0.1547(2) 0.15388(14) 0.35039(12) 0.0601(5) Uani 1 1 d . . .
Cl2 Cl 0.22980(19) 0.05435(12) 0.75912(11) 0.0463(4) Uani 1 1 d . . .
Cl3 Cl 0.9494(2) -0.31945(15) 0.37920(12) 0.0548(4) Uani 1 1 d . . .
Cl4 Cl 0.89180(18) -0.22136(12) -0.04595(10) 0.0446(3) Uani 1 1 d . . .
C1 C 0.5187(8) -0.1557(5) 0.5656(4) 0.0309(11) Uani 1 1 d . . .
C2 C 0.3998(8) -0.0854(5) 0.5037(4) 0.0347(11) Uani 1 1 d . . .
H2 H 0.2658 -0.1255 0.4821 0.042 Uiso 1 1 calc R . .
N3 N 0.4768(8) 0.0419(5) 0.4744(4) 0.0420(11) Uani 1 1 d . . .
H3 H 0.391(8) 0.069(5) 0.435(4) 0.036(14) Uiso 1 1 d . . .
C4 C 0.6684(10) 0.1024(6) 0.5032(5) 0.0436(14) Uani 1 1 d . . .
H4 H 0.7172 0.1894 0.4812 0.052 Uiso 1 1 calc R . .
C5 C 0.7928(9) 0.0387(6) 0.5639(5) 0.0454(14) Uani 1 1 d . . .
H5 H 0.9263 0.0810 0.5844 0.054 Uiso 1 1 calc R . .
C6 C 0.7149(9) -0.0929(6) 0.5952(5) 0.0386(13) Uani 1 1 d . . .
H6 H 0.7983 -0.1383 0.6368 0.046 Uiso 1 1 calc R . .
C7 C 0.4237(7) -0.2996(4) 0.5933(4) 0.0310(9) Uani 1 1 d . . .
H7 H 0.3319 -0.3518 0.5256 0.037 Uiso 1 1 calc R . .
N8 N 0.2956(6) -0.2642(4) 0.6966(3) 0.0298(9) Uani 1 1 d . . .
H8 H 0.269(13) -0.160(8) 0.698(6) 0.13(3) Uiso 1 1 d . . .
C9 C 0.3919(8) -0.2707(5) 0.8141(4) 0.0393(12) Uani 1 1 d . . .
H9A H 0.3280 -0.2120 0.8756 0.047 Uiso 1 1 calc R . .
H9B H 0.5329 -0.2287 0.8199 0.047 Uiso 1 1 calc R . .
C10 C 0.3739(11) -0.4287(6) 0.8326(5) 0.0543(17) Uani 1 1 d . . .
H10A H 0.5030 -0.4445 0.8635 0.065 Uiso 1 1 calc R . .
H10B H 0.2776 -0.4413 0.8901 0.065 Uiso 1 1 calc R . .
C11 C 0.3076(10) -0.5431(6) 0.7206(5) 0.0483(15) Uani 1 1 d . . .
H11 H 0.2851 -0.6389 0.7420 0.058 Uiso 1 1 calc R . .
C12 C 0.1076(10) -0.5197(7) 0.6666(6) 0.0604(17) Uani 1 1 d . . .
H12A H 0.0913 -0.5696 0.5848 0.073 Uiso 1 1 calc R . .
H12B H -0.0013 -0.5632 0.7057 0.073 Uiso 1 1 calc R . .
C13 C 0.0935(8) -0.3581(6) 0.6759(5) 0.0428(13) Uani 1 1 d . . .
H13A H 0.0267 -0.3460 0.6043 0.051 Uiso 1 1 calc R . .
H13B H 0.0125 -0.3256 0.7397 0.051 Uiso 1 1 calc R . .
C14 C 0.5713(8) -0.4007(5) 0.6132(5) 0.0441(12) Uani 1 1 d . . .
H14A H 0.6624 -0.3524 0.6810 0.053 Uiso 1 1 calc R . .
H14B H 0.6507 -0.4173 0.5461 0.053 Uiso 1 1 calc R . .
C15 C 0.4717(10) -0.5493(6) 0.6324(5) 0.0507(15) Uani 1 1 d . . .
H15A H 0.5753 -0.5991 0.6593 0.061 Uiso 1 1 calc R . .
H15B H 0.4120 -0.6084 0.5577 0.061 Uiso 1 1 calc R . .
C21 C 0.5729(8) -0.0215(6) 0.1317(4) 0.0319(11) Uani 1 1 d . . .
C22 C 0.7179(9) -0.0658(6) 0.1971(4) 0.0400(13) Uani 1 1 d . . .
H22 H 0.8482 -0.0144 0.2094 0.048 Uiso 1 1 calc R . .
N23 N 0.6692(8) -0.1825(5) 0.2421(4) 0.0391(11) Uani 1 1 d . . .
H23 H 0.773(10) -0.216(6) 0.281(5) 0.07(2) Uiso 1 1 d . . .
C24 C 0.4887(11) -0.2614(7) 0.2287(5) 0.0486(15) Uani 1 1 d . . .
H24 H 0.4642 -0.3442 0.2606 0.058 Uiso 1 1 calc R . .
C25 C 0.3363(9) -0.2193(6) 0.1665(5) 0.0492(15) Uani 1 1 d . . .
H25 H 0.2064 -0.2710 0.1582 0.059 Uiso 1 1 calc R . .
C26 C 0.3800(8) -0.1000(6) 0.1173(4) 0.0377(12) Uani 1 1 d . . .
H26 H 0.2796 -0.0714 0.0740 0.045 Uiso 1 1 calc R . .
C27 C 0.6206(7) 0.1101(4) 0.0738(4) 0.0353(10) Uani 1 1 d . . .
H27 H 0.5019 0.1113 0.0227 0.042 Uiso 1 1 calc R . .
N28 N 0.7931(6) 0.0902(4) -0.0032(3) 0.0292(9) Uani 1 1 d . . .
H28 H 0.820(6) -0.002(4) -0.016(3) 0.020(10) Uiso 1 1 d . . .
C29 C 0.7497(9) 0.1221(6) -0.1199(4) 0.0425(13) Uani 1 1 d . . .
H29A H 0.6284 0.0589 -0.1580 0.051 Uiso 1 1 calc R . .
H29B H 0.8597 0.1017 -0.1683 0.051 Uiso 1 1 calc R . .
C30 C 0.7226(11) 0.2822(7) -0.1079(5) 0.0615(18) Uani 1 1 d . . .
H30A H 0.7810 0.3182 -0.1726 0.074 Uiso 1 1 calc R . .
H30B H 0.5799 0.2878 -0.1136 0.074 Uiso 1 1 calc R . .
C31 C 0.8178(11) 0.3811(6) 0.0059(5) 0.0581(18) Uani 1 1 d . . .
H31 H 0.8486 0.4806 -0.0081 0.070 Uiso 1 1 calc R . .
C32 C 1.0185(11) 0.3327(7) 0.0352(6) 0.063(2) Uani 1 1 d . . .
H32A H 1.1086 0.3480 -0.0248 0.076 Uiso 1 1 calc R . .
H32B H 1.0791 0.3941 0.1089 0.076 Uiso 1 1 calc R . .
C33 C 0.9973(8) 0.1718(6) 0.0444(5) 0.0399(12) Uani 1 1 d . . .
H33A H 1.0990 0.1255 0.0012 0.048 Uiso 1 1 calc R . .
H33B H 1.0193 0.1667 0.1257 0.048 Uiso 1 1 calc R . .
C34 C 0.6581(10) 0.2558(5) 0.1619(5) 0.0572(14) Uani 1 1 d . . .
H34A H 0.7780 0.2588 0.2120 0.069 Uiso 1 1 calc R . .
H34B H 0.5460 0.2614 0.2109 0.069 Uiso 1 1 calc R . .
C35 C 0.6844(12) 0.3892(6) 0.1068(6) 0.070(2) Uani 1 1 d . . .
H35A H 0.5526 0.4044 0.0794 0.084 Uiso 1 1 calc R . .
H35B H 0.7396 0.4747 0.1671 0.084 Uiso 1 1 calc R . .
O1 O 0.2793(8) 0.4760(5) 0.3214(5) 0.0793(13) Uani 1 1 d D . .
H1A H 0.255(11) 0.397(4) 0.345(5) 0.095 Uiso 1 1 d D . .
H1B H 0.165(6) 0.506(7) 0.326(6) 0.095 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 117.8(4) . . ?
C6 C1 C7 124.6(4) . . ?
C2 C1 C7 117.6(4) . . ?
N3 C2 C1 120.4(5) . . ?
N3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 N3 C2 121.6(5) . . ?
C4 N3 H3 128(3) . . ?
C2 N3 H3 110(3) . . ?
N3 C4 C5 120.8(5) . . ?
N3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 118.3(6) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C1 C6 C5 121.2(5) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C14 C7 C1 114.6(4) . . ?
C14 C7 N8 112.4(3) . . ?
C1 C7 N8 108.2(3) . . ?
C14 C7 H7 107.1 . . ?
C1 C7 H7 107.1 . . ?
N8 C7 H7 107.1 . . ?
C13 N8 C9 109.4(4) . . ?
C13 N8 C7 111.8(4) . . ?
C9 N8 C7 115.4(4) . . ?
C13 N8 H8 106(5) . . ?
C9 N8 H8 109(4) . . ?
C7 N8 H8 105(4) . . ?
N8 C9 C10 112.1(4) . . ?
N8 C9 H9A 109.2 . . ?
C10 C9 H9A 109.2 . . ?
N8 C9 H9B 109.2 . . ?
C10 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 112.7(4) . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 C12 110.9(6) . . ?
C10 C11 C15 112.3(5) . . ?
C12 C11 C15 112.1(5) . . ?
C10 C11 H11 107.1 . . ?
C12 C11 H11 107.1 . . ?
C15 C11 H11 107.1 . . ?
C13 C12 C11 112.4(5) . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
N8 C13 C12 112.2(5) . . ?
N8 C13 H13A 109.2 . . ?
C12 C13 H13A 109.2 . . ?
N8 C13 H13B 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C7 C14 C15 113.8(4) . . ?
C7 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
C7 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 C11 115.5(5) . . ?
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 . . ?
C22 C21 C26 118.5(4) . . ?
C22 C21 C27 121.7(5) . . ?
C26 C21 C27 119.8(4) . . ?
N23 C22 C21 119.0(5) . . ?
N23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C24 N23 C22 124.3(5) . . ?
C24 N23 H23 118(4) . . ?
C22 N23 H23 118(4) . . ?
N23 C24 C25 118.9(5) . . ?
N23 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
C26 C25 C24 118.8(5) . . ?
C26 C25 H25 120.6 . . ?
C24 C25 H25 120.6 . . ?
C25 C26 C21 120.4(5) . . ?
C25 C26 H26 119.8 . . ?
C21 C26 H26 119.8 . . ?
N28 C27 C34 112.1(4) . . ?
N28 C27 C21 110.5(3) . . ?
C34 C27 C21 112.6(4) . . ?
N28 C27 H27 107.1 . . ?
C34 C27 H27 107.1 . . ?
C21 C27 H27 107.1 . . ?
C29 N28 C33 107.8(4) . . ?
C29 N28 C27 112.1(4) . . ?
C33 N28 C27 117.7(4) . . ?
C29 N28 H28 107(3) . . ?
C33 N28 H28 100(3) . . ?
C27 N28 H28 112(3) . . ?
N28 C29 C30 110.6(4) . . ?
N28 C29 H29A 109.5 . . ?
C30 C29 H29A 109.5 . . ?
N28 C29 H29B 109.5 . . ?
C30 C29 H29B 109.5 . . ?
H29A C29 H29B 108.1 . . ?
C31 C30 C29 113.6(5) . . ?
C31 C30 H30A 108.8 . . ?
C29 C30 H30A 108.8 . . ?
C31 C30 H30B 108.8 . . ?
C29 C30 H30B 108.8 . . ?
H30A C30 H30B 107.7 . . ?
C35 C31 C30 114.6(6) . . ?
C35 C31 C32 112.0(6) . . ?
C30 C31 C32 108.3(6) . . ?
C35 C31 H31 107.2 . . ?
C30 C31 H31 107.2 . . ?
C32 C31 H31 107.2 . . ?
C33 C32 C31 113.4(5) . . ?
C33 C32 H32A 108.9 . . ?
C31 C32 H32A 108.9 . . ?
C33 C32 H32B 108.9 . . ?
C31 C32 H32B 108.9 . . ?
H32A C32 H32B 107.7 . . ?
N28 C33 C32 111.4(4) . . ?
N28 C33 H33A 109.3 . . ?
C32 C33 H33A 109.3 . . ?
N28 C33 H33B 109.3 . . ?
C32 C33 H33B 109.3 . . ?
H33A C33 H33B 108.0 . . ?
C27 C34 C35 114.0(5) . . ?
C27 C34 H34A 108.8 . . ?
C35 C34 H34A 108.8 . . ?
C27 C34 H34B 108.8 . . ?
C35 C34 H34B 108.8 . . ?
H34A C34 H34B 107.7 . . ?
C31 C35 C34 115.9(5) . . ?
C31 C35 H35A 108.3 . . ?
C34 C35 H35A 108.3 . . ?
C31 C35 H35B 108.3 . . ?
C34 C35 H35B 108.3 . . ?
H35A C35 H35B 107.4 . . ?
H1A O1 H1B 101(6) . . ?
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 1.367(7) . ?
C1 C2 1.379(7) . ?
C1 C7 1.520(6) . ?
C2 N3 1.355(6) . ?
C2 H2 0.9300 . ?
N3 C4 1.333(7) . ?
N3 H3 0.82(5) . ?
C4 C5 1.355(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.404(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C14 1.513(6) . ?
C7 N8 1.527(6) . ?
C7 H7 0.9800 . ?
N8 C13 1.495(6) . ?
N8 C9 1.512(5) . ?
N8 H8 1.02(8) . ?
C9 C10 1.537(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.518(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.526(9) . ?
C11 C15 1.546(9) . ?
C11 H11 0.9800 . ?
C12 C13 1.520(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.530(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C21 C22 1.376(7) . ?
C21 C26 1.386(7) . ?
C21 C27 1.536(6) . ?
C22 N23 1.323(6) . ?
C22 H22 0.9300 . ?
N23 C24 1.317(8) . ?
N23 H23 0.95(6) . ?
C24 C25 1.383(8) . ?
C24 H24 0.9300 . ?
C25 C26 1.368(7) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 N28 1.512(6) . ?
C27 C34 1.518(6) . ?
C27 H27 0.9800 . ?
N28 C29 1.486(5) . ?
N28 C33 1.499(6) . ?
N28 H28 0.89(4) . ?
C29 C30 1.523(8) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.515(8) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C35 1.514(9) . ?
C31 C32 1.533(10) . ?
C31 H31 0.9800 . ?
C32 C33 1.529(8) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 C35 1.521(8) . ?
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 0.82(5) 2.17(5) 2.988(5) 174(5) .
N8 H8 Cl2 1.02(8) 2.05(8) 3.039(4) 161(6) .
N23 H23 Cl3 0.95(6) 2.08(6) 3.013(5) 167(5) .
N28 H28 Cl4 0.89(4) 2.15(4) 3.046(4) 179(4) .
O1 H1A Cl1 0.85(2) 2.31(3) 3.124(4) 162(6) .
O1 H1B Cl3 0.86(2) 2.35(4) 3.149(5) 155(7) 1_465
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 -0.2(7) . . . . ?
C7 C1 C2 N3 -178.7(5) . . . . ?
C1 C2 N3 C4 0.5(8) . . . . ?
C2 N3 C4 C5 -0.5(9) . . . . ?
N3 C4 C5 C6 0.3(9) . . . . ?
C2 C1 C6 C5 0.1(7) . . . . ?
C7 C1 C6 C5 178.5(5) . . . . ?
C4 C5 C6 C1 -0.1(8) . . . . ?
C6 C1 C7 C14 -23.0(6) . . . . ?
C2 C1 C7 C14 155.4(4) . . . . ?
C6 C1 C7 N8 103.3(5) . . . . ?
C2 C1 C7 N8 -78.3(5) . . . . ?
C14 C7 N8 C13 -98.5(5) . . . . ?
C1 C7 N8 C13 134.0(4) . . . . ?
C14 C7 N8 C9 27.3(5) . . . . ?
C1 C7 N8 C9 -100.2(4) . . . . ?
C13 N8 C9 C10 46.1(6) . . . . ?
C7 N8 C9 C10 -81.0(6) . . . . ?
N8 C9 C10 C11 12.9(8) . . . . ?
C9 C10 C11 C12 -57.0(7) . . . . ?
C9 C10 C11 C15 69.2(7) . . . . ?
C10 C11 C12 C13 39.4(7) . . . . ?
C15 C11 C12 C13 -86.9(7) . . . . ?
C9 N8 C13 C12 -64.5(6) . . . . ?
C7 N8 C13 C12 64.6(5) . . . . ?
C11 C12 C13 N8 19.7(7) . . . . ?
C1 C7 C14 C15 -175.9(4) . . . . ?
N8 C7 C14 C15 60.0(6) . . . . ?
C7 C14 C15 C11 -47.2(7) . . . . ?
C10 C11 C15 C14 -46.5(7) . . . . ?
C12 C11 C15 C14 79.1(7) . . . . ?
C26 C21 C22 N23 1.1(8) . . . . ?
C27 C21 C22 N23 -178.1(4) . . . . ?
C21 C22 N23 C24 0.1(8) . . . . ?
C22 N23 C24 C25 -1.9(9) . . . . ?
N23 C24 C25 C26 2.4(9) . . . . ?
C24 C25 C26 C21 -1.2(9) . . . . ?
C22 C21 C26 C25 -0.5(8) . . . . ?
C27 C21 C26 C25 178.7(5) . . . . ?
C22 C21 C27 N28 55.0(6) . . . . ?
C26 C21 C27 N28 -124.2(5) . . . . ?
C22 C21 C27 C34 -71.2(6) . . . . ?
C26 C21 C27 C34 109.7(6) . . . . ?
C34 C27 N28 C29 -100.5(5) . . . . ?
C21 C27 N28 C29 133.0(4) . . . . ?
C34 C27 N28 C33 25.4(5) . . . . ?
C21 C27 N28 C33 -101.0(5) . . . . ?
C33 N28 C29 C30 -68.1(6) . . . . ?
C27 N28 C29 C30 63.0(6) . . . . ?
N28 C29 C30 C31 21.3(8) . . . . ?
C29 C30 C31 C35 -86.9(7) . . . . ?
C29 C30 C31 C32 38.9(8) . . . . ?
C35 C31 C32 C33 70.0(7) . . . . ?
C30 C31 C32 C33 -57.3(7) . . . . ?
C29 N28 C33 C32 49.1(6) . . . . ?
C27 N28 C33 C32 -78.9(5) . . . . ?
C31 C32 C33 N28 12.6(7) . . . . ?
N28 C27 C34 C35 60.7(6) . . . . ?
C21 C27 C34 C35 -174.0(5) . . . . ?
C30 C31 C35 C34 75.0(8) . . . . ?
C32 C31 C35 C34 -48.9(8) . . . . ?
C27 C34 C35 C31 -44.2(8) . . . . ?
