#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:02:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178417 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/38/4023859.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_4023859
loop_
_publ_author_name
'M. Arunachalam'
'I. Ravikumar'
'Pradyut Ghosh'
_publ_section_title
;
 A New Hexaaza Bicyclic Cyclophane with Dual Binding Sites
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9144
_journal_page_last               9147
_journal_paper_doi               10.1021/jo801762b
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C48 H80 Cl6 N6 O9'
_chemical_formula_weight         1097.88
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.732(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.3385(7)
_cell_length_b                   16.9020(7)
_cell_length_c                   18.5010(8)
_cell_measurement_temperature    100(2)
_cell_volume                     5410.3(4)
_computing_cell_refinement       'BRUKER AXS SMART 3'
_computing_data_collection       'BRUKER AXS SMART 3'
_computing_data_reduction        'BRUKER AXS SAINT'
_computing_molecular_graphics    'BRUKER SHELXLTL'
_computing_publication_material  'MERCURY 1.4.1'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 3
_diffrn_measured_fraction_theta_full 0.919
_diffrn_measured_fraction_theta_max 0.919
_diffrn_measurement_device_type  'BRUKER CCD AREA DETECTOR'
_diffrn_measurement_method       'OMEGA SCAN'
_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  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0461
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            42187
_diffrn_reflns_theta_full        27.95
_diffrn_reflns_theta_max         27.95
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.376
_exptl_absorpt_correction_T_max  0.9563
_exptl_absorpt_correction_T_min  0.8643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             2336
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.748
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     942
_refine_ls_number_reflns         11941
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0439
_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)+(0.0506P)²+6.8861P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1426
_reflns_number_gt                7894
_reflns_number_total             11941
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801762b_si_001.cif
_cod_data_source_block           isocl_0m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'MONOCLINIC' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed
to 'multi-scan' 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_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023859
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.04296(4) 0.70613(4) 0.09424(4) 0.02570(16) Uani 1 1 d . . .
Cl2 Cl 0.40249(4) 0.59745(5) 0.16317(4) 0.03167(18) Uani 1 1 d . . .
Cl3 Cl 0.22904(4) 0.93307(5) 0.22549(4) 0.02629(16) Uani 1 1 d . . .
Cl4 Cl 0.82926(4) 0.39099(5) 0.41940(4) 0.03068(18) Uani 1 1 d . . .
Cl5 Cl 0.62798(5) 0.98396(6) 0.29815(4) 0.0466(3) Uani 1 1 d . . .
Cl6 Cl 0.64715(5) 0.60902(5) 0.12650(5) 0.0419(2) Uani 1 1 d . . .
C1 C 0.38279(15) 0.17519(16) 0.14060(14) 0.0185(5) Uani 1 1 d . . .
C2 C 0.45077(15) 0.17664(17) 0.18685(15) 0.0202(6) Uani 1 1 d . . .
C3 C 0.48544(15) 0.24878(18) 0.20840(14) 0.0205(6) Uani 1 1 d . . .
C4 C 0.45133(15) 0.32041(17) 0.18473(14) 0.0191(6) Uani 1 1 d . . .
C5 C 0.38343(15) 0.31979(17) 0.13771(14) 0.0188(6) Uani 1 1 d . . .
C6 C 0.34973(15) 0.24714(17) 0.11682(14) 0.0187(6) Uani 1 1 d . . .
C7 C 0.34879(17) 0.09729(18) 0.11436(17) 0.0222(6) Uani 1 1 d . . .
C8 C 0.56064(16) 0.2490(2) 0.25455(17) 0.0256(6) Uani 1 1 d . . .
C9 C 0.35021(17) 0.39609(18) 0.10761(17) 0.0225(6) Uani 1 1 d . . .
C10 C 0.27962(15) 0.24572(18) 0.06328(15) 0.0191(6) Uani 1 1 d . . .
C11 C 0.17762(16) 0.29922(18) 0.14139(16) 0.0208(6) Uani 1 1 d . . .
C12 C 0.09955(15) 0.28395(16) 0.17066(15) 0.0197(6) Uani 1 1 d . . .
C13 C 0.03635(16) 0.26177(18) 0.12464(16) 0.0229(6) Uani 1 1 d . . .
C14 C -0.03519(16) 0.2504(2) 0.15203(16) 0.0279(7) Uani 1 1 d . . .
C15 C -0.04485(16) 0.2625(2) 0.22450(16) 0.0276(7) Uani 1 1 d . . .
C16 C 0.01717(15) 0.28553(17) 0.27110(15) 0.0208(6) Uani 1 1 d . . .
C17 C 0.08964(15) 0.29517(17) 0.24332(15) 0.0202(6) Uani 1 1 d . . .
C18 C 0.00580(17) 0.30218(18) 0.34954(15) 0.0225(6) Uani 1 1 d . . .
C19 C -0.02552(15) 0.23948(19) 0.46881(15) 0.0216(6) Uani 1 1 d . . .
C20 C 0.04877(14) 0.24528(17) 0.51636(14) 0.0182(6) Uani 1 1 d . . .
C21 C 0.07921(15) 0.31826(17) 0.53774(14) 0.0204(6) Uani 1 1 d . . .
C22 C 0.14767(15) 0.32127(17) 0.58390(14) 0.0202(6) Uani 1 1 d . . .
C23 C 0.18327(14) 0.25180(17) 0.60909(14) 0.0197(6) Uani 1 1 d . . .
C24 C 0.15193(15) 0.17818(17) 0.58756(14) 0.0185(6) Uani 1 1 d . . .
C25 C 0.08433(15) 0.17389(17) 0.54146(14) 0.0190(6) Uani 1 1 d . . .
C26 C 0.04769(17) 0.09539(18) 0.52025(17) 0.0230(6) Uani 1 1 d . . .
C27 C 0.25290(16) 0.2539(2) 0.66332(17) 0.0243(6) Uani 1 1 d . . .
C28 C 0.04005(17) 0.39555(19) 0.51537(17) 0.0238(6) Uani 1 1 d . . .
C29 C 0.17954(17) 0.40149(19) 0.60665(16) 0.0241(6) Uani 1 1 d . . .
C30 C 0.31073(15) 0.41094(19) 0.55496(16) 0.0229(6) Uani 1 1 d . . .
C31 C 0.35742(15) 0.45416(17) 0.50175(15) 0.0209(6) Uani 1 1 d . . .
C32 C 0.37386(16) 0.53457(18) 0.51128(16) 0.0233(6) Uani 1 1 d . . .
C33 C 0.42127(16) 0.57262(19) 0.46499(16) 0.0250(6) Uani 1 1 d . . .
C34 C 0.45235(16) 0.53211(18) 0.40884(16) 0.0239(6) Uani 1 1 d . . .
C35 C 0.43533(15) 0.45245(17) 0.39783(15) 0.0214(6) Uani 1 1 d . . .
C36 C 0.38805(15) 0.41410(19) 0.44442(15) 0.0217(6) Uani 1 1 d . . .
C37 C 0.47145(17) 0.40669(19) 0.33928(16) 0.0237(6) Uani 1 1 d . . .
C38 C 0.48919(16) 0.39837(18) 0.20453(16) 0.0231(6) Uani 1 1 d . . .
C39 C 0.48909(16) 0.09992(18) 0.21041(15) 0.0217(6) Uani 1 1 d . . .
C40 C 0.39754(16) 0.03651(19) 0.29334(16) 0.0233(6) Uani 1 1 d . . .
C41 C 0.38782(15) 0.01022(17) 0.36966(15) 0.0211(6) Uani 1 1 d . . .
C42 C 0.44219(16) -0.03848(18) 0.40569(16) 0.0230(6) Uani 1 1 d . . .
C43 C 0.43124(17) -0.06449(18) 0.47541(16) 0.0243(6) Uani 1 1 d . . .
C44 C 0.36535(17) -0.04327(18) 0.50905(16) 0.0235(6) Uani 1 1 d . . .
C45 C 0.31075(15) 0.00645(17) 0.47385(15) 0.0214(6) Uani 1 1 d . . .
C46 C 0.32246(16) 0.03237(18) 0.40440(16) 0.0219(6) Uani 1 1 d . . .
C47 C 0.23964(16) 0.03068(19) 0.51052(16) 0.0237(6) Uani 1 1 d . . .
C48 C 0.19139(16) 0.10411(19) 0.61771(16) 0.0227(6) Uani 1 1 d . . .
N1 N 0.20404(13) 0.23196(15) 0.09693(14) 0.0203(5) Uani 1 1 d . . .
N2 N -0.01310(14) 0.22810(15) 0.38950(13) 0.0211(5) Uani 1 1 d . . .
N3 N 0.22804(13) 0.43823(16) 0.55056(14) 0.0217(5) Uani 1 1 d . . .
N4 N 0.45409(15) 0.44179(16) 0.26575(13) 0.0225(5) Uani 1 1 d . . .
N5 N 0.47417(13) 0.07563(16) 0.28635(13) 0.0209(5) Uani 1 1 d . . .
N6 N 0.25991(13) 0.08049(16) 0.57606(13) 0.0212(5) Uani 1 1 d . . .
O1 O 0.18955(15) 0.75198(17) 0.19871(14) 0.0344(5) Uani 1 1 d . . .
O2 O 0.29202(14) 0.72890(16) 0.10033(13) 0.0344(5) Uani 1 1 d . . .
O3 O 0.37329(16) 0.74074(16) 0.53883(13) 0.0349(6) Uani 1 1 d . . .
O4 O 0.31621(13) 0.89057(17) 0.08802(13) 0.0306(5) Uani 1 1 d . . .
O5 O 0.27212(15) 0.75292(18) 0.64401(14) 0.0515(7) Uani 1 1 d . . .
O6 O 0.58322(15) 0.54427(17) 0.27554(15) 0.0413(6) Uani 1 1 d . . .
O7 O 0.32086(15) 0.21068(14) 0.50987(13) 0.0291(5) Uani 1 1 d . . .
O8 O 0.19789(16) 0.11680(17) 0.20079(15) 0.0389(6) Uani 1 1 d . . .
O9 O 0.72198(15) 0.45932(17) 0.29099(13) 0.0503(7) Uani 1 1 d . . .
H1A H 0.2049(17) 0.190(2) 0.1251(17) 0.023(8) Uiso 1 1 d . . .
H1B H 0.171(2) 0.225(2) 0.061(2) 0.039(10) Uiso 1 1 d . . .
H1C H 0.151(3) 0.744(3) 0.179(3) 0.064(16) Uiso 1 1 d . . .
H1D H 0.191(2) 0.801(3) 0.204(2) 0.050(13) Uiso 1 1 d . . .
H2A H 0.023(2) 0.190(2) 0.3822(18) 0.036(10) Uiso 1 1 d . . .
H2B H -0.0582(19) 0.2054(18) 0.3684(17) 0.023(8) Uiso 1 1 d . . .
H2C H 0.318(3) 0.689(3) 0.115(2) 0.056(14) Uiso 1 1 d . . .
H2D H 0.262(3) 0.731(3) 0.136(3) 0.072(15) Uiso 1 1 d . . .
H3A H 0.2086(18) 0.4259(19) 0.5031(19) 0.028(9) Uiso 1 1 d . . .
H3B H 0.2260(18) 0.490(2) 0.5582(17) 0.026(9) Uiso 1 1 d . . .
H4A H 0.404(2) 0.443(2) 0.2591(19) 0.036(10) Uiso 1 1 d . . .
H4B H 0.4749(18) 0.489(2) 0.2648(17) 0.026(9) Uiso 1 1 d . . .
H4C H 0.310(2) 0.843(2) 0.0865(19) 0.030(10) Uiso 1 1 d . . .
H4D H 0.288(2) 0.909(2) 0.120(2) 0.041(11) Uiso 1 1 d . . .
H5A H 0.510(2) 0.044(2) 0.3005(18) 0.033(9) Uiso 1 1 d . . .
H5B H 0.476(2) 0.120(2) 0.315(2) 0.044(11) Uiso 1 1 d . . .
H6A H 0.2827(18) 0.124(2) 0.5602(17) 0.026(9) Uiso 1 1 d . . .
H6B H 0.292(2) 0.054(2) 0.609(2) 0.040(10) Uiso 1 1 d . . .
H6C H 0.590(3) 0.566(3) 0.236(3) 0.069(15) Uiso 1 1 d . . .
H6D H 0.630(3) 0.512(3) 0.276(3) 0.080(16) Uiso 1 1 d . . .
H7A H 0.338(2) 0.061(2) 0.150(2) 0.044(10) Uiso 1 1 d . . .
H7B H 0.379(2) 0.071(2) 0.080(2) 0.047(11) Uiso 1 1 d . . .
H7C H 0.299(3) 0.099(2) 0.088(2) 0.059(12) Uiso 1 1 d . . .
H7D H 0.287(2) 0.216(2) 0.484(2) 0.046(13) Uiso 1 1 d . . .
H7E H 0.361(3) 0.201(3) 0.489(2) 0.059(13) Uiso 1 1 d . . .
H8A H 0.600(3) 0.278(3) 0.234(2) 0.065(13) Uiso 1 1 d . . .
H8B H 0.581(3) 0.198(3) 0.267(2) 0.072(14) Uiso 1 1 d . . .
H8C H 0.559(3) 0.281(3) 0.298(3) 0.081(15) Uiso 1 1 d . . .
H8D H 0.205(2) 0.068(3) 0.201(2) 0.046(12) Uiso 1 1 d . . .
H8E H 0.174(2) 0.120(3) 0.230(2) 0.046(14) Uiso 1 1 d . . .
H9A H 0.376(2) 0.445(2) 0.125(2) 0.045(10) Uiso 1 1 d . . .
H9B H 0.353(2) 0.399(2) 0.059(2) 0.038(10) Uiso 1 1 d . . .
H9C H 0.296(2) 0.401(2) 0.117(2) 0.053(11) Uiso 1 1 d . . .
H10A H 0.2842(15) 0.2048(17) 0.0283(15) 0.011(7) Uiso 1 1 d . . .
H10B H 0.2734(15) 0.2962(17) 0.0368(14) 0.010(7) Uiso 1 1 d . . .
H11A H 0.1756(16) 0.3445(18) 0.1125(16) 0.017(7) Uiso 1 1 d . . .
H11B H 0.2167(18) 0.3065(19) 0.1797(17) 0.026(8) Uiso 1 1 d . . .
H13 H 0.0433(16) 0.2550(16) 0.0721(16) 0.016(7) Uiso 1 1 d . . .
H14 H -0.077(2) 0.233(2) 0.1210(19) 0.037(9) Uiso 1 1 d . . .
H15 H -0.096(2) 0.255(2) 0.2445(19) 0.039(10) Uiso 1 1 d . . .
H17 H 0.1319(16) 0.3113(16) 0.2745(15) 0.011(7) Uiso 1 1 d . . .
H18A H -0.0382(17) 0.3389(18) 0.3540(15) 0.019(7) Uiso 1 1 d . . .
H18B H 0.0499(18) 0.3217(18) 0.3739(16) 0.022(8) Uiso 1 1 d . . .
H19A H -0.0574(17) 0.2873(19) 0.4736(16) 0.021(8) Uiso 1 1 d . . .
H19B H -0.0541(16) 0.1949(18) 0.4823(15) 0.016(7) Uiso 1 1 d . . .
H26A H 0.0708(19) 0.048(2) 0.5427(18) 0.031(9) Uiso 1 1 d . . .
H26B H 0.048(2) 0.085(2) 0.468(2) 0.056(12) Uiso 1 1 d . . .
H26C H 0.000(3) 0.093(2) 0.538(2) 0.062(13) Uiso 1 1 d . . .
H27A H 0.277(2) 0.304(3) 0.668(2) 0.062(13) Uiso 1 1 d . . .
H27B H 0.289(2) 0.212(2) 0.655(2) 0.053(11) Uiso 1 1 d . . .
H27C H 0.241(2) 0.242(2) 0.710(2) 0.045(11) Uiso 1 1 d . . .
H28A H -0.003(2) 0.389(2) 0.486(2) 0.053(12) Uiso 1 1 d . . .
H28B H 0.027(2) 0.425(2) 0.558(2) 0.045(10) Uiso 1 1 d . . .
H28C H 0.072(2) 0.429(2) 0.487(2) 0.055(12) Uiso 1 1 d . . .
H29A H 0.2120(17) 0.4013(17) 0.6529(16) 0.018(7) Uiso 1 1 d . . .
H29B H 0.1402(17) 0.4365(18) 0.6121(16) 0.018(7) Uiso 1 1 d . . .
H30A H 0.3079(16) 0.3522(19) 0.5439(16) 0.021(8) Uiso 1 1 d . . .
H30B H 0.3305(16) 0.4196(17) 0.6041(16) 0.016(7) Uiso 1 1 d . . .
H32 H 0.3532(19) 0.565(2) 0.5505(18) 0.032(9) Uiso 1 1 d . . .
H33 H 0.4345(18) 0.625(2) 0.4744(17) 0.028(9) Uiso 1 1 d . . .
H34 H 0.4852(17) 0.5595(18) 0.3782(16) 0.022(8) Uiso 1 1 d . . .
H36 H 0.3786(18) 0.361(2) 0.4405(17) 0.031(9) Uiso 1 1 d . . .
H37A H 0.523(2) 0.4076(19) 0.3460(18) 0.032(9) Uiso 1 1 d . . .
H37B H 0.4537(17) 0.3490(19) 0.3366(16) 0.020(8) Uiso 1 1 d . . .
H38A H 0.4851(17) 0.4375(19) 0.1621(17) 0.026(8) Uiso 1 1 d . . .
H38B H 0.5432(18) 0.3948(17) 0.2214(16) 0.019(7) Uiso 1 1 d . . .
H39A H 0.4729(15) 0.0558(17) 0.1798(15) 0.011(7) Uiso 1 1 d . . .
H39B H 0.546(2) 0.1001(19) 0.2074(17) 0.031(9) Uiso 1 1 d . . .
H40A H 0.3590(18) 0.0721(19) 0.2760(16) 0.022(8) Uiso 1 1 d . . .
H40B H 0.396(2) -0.009(2) 0.2624(19) 0.039(10) Uiso 1 1 d . . .
H42 H 0.4853(18) -0.0538(19) 0.3824(17) 0.024(8) Uiso 1 1 d . . .
H43 H 0.4664(18) -0.0995(19) 0.4977(17) 0.025(8) Uiso 1 1 d . . .
H44 H 0.3567(19) -0.063(2) 0.5569(19) 0.035(9) Uiso 1 1 d . . .
H46 H 0.2884(17) 0.0652(18) 0.3814(16) 0.020(8) Uiso 1 1 d . . .
H47A H 0.2150(18) -0.013(2) 0.5266(17) 0.025(8) Uiso 1 1 d . . .
H47B H 0.2044(17) 0.0611(18) 0.4778(16) 0.018(7) Uiso 1 1 d . . .
H48A H 0.2109(16) 0.1112(17) 0.6673(17) 0.017(7) Uiso 1 1 d . . .
H48B H 0.1581(17) 0.0579(18) 0.6188(15) 0.018(7) Uiso 1 1 d . . .
H100 H 0.407(3) 0.754(3) 0.554(2) 0.046(14) Uiso 1 1 d . . .
H101 H 0.341(3) 0.746(3) 0.576(3) 0.089(17) Uiso 1 1 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 118.9(3) . . ?
C6 C1 C7 120.8(2) . . ?
C2 C1 C7 120.2(2) . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 C39 119.5(2) . . ?
C1 C2 C39 119.7(3) . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 C8 120.3(3) . . ?
C2 C3 C8 119.9(3) . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 C38 120.7(2) . . ?
C5 C4 C38 119.1(3) . . ?
C6 C5 C4 119.3(2) . . ?
C6 C5 C9 120.4(2) . . ?
C4 C5 C9 120.2(3) . . ?
C1 C6 C5 121.2(2) . . ?
C1 C6 C10 119.0(2) . . ?
C5 C6 C10 119.7(2) . . ?
C1 C7 H7A 116(2) . . ?
C1 C7 H7B 114(2) . . ?
H7A C7 H7B 108(3) . . ?
C1 C7 H7C 117(2) . . ?
H7A C7 H7C 99(3) . . ?
H7B C7 H7C 102(3) . . ?
C3 C8 H8A 113(3) . . ?
C3 C8 H8B 115(3) . . ?
H8A C8 H8B 108(4) . . ?
C3 C8 H8C 114(3) . . ?
H8A C8 H8C 97(4) . . ?
H8B C8 H8C 109(4) . . ?
C5 C9 H9A 117(2) . . ?
C5 C9 H9B 112(2) . . ?
H9A C9 H9B 102(3) . . ?
C5 C9 H9C 111(2) . . ?
H9A C9 H9C 107(3) . . ?
H9B C9 H9C 107(3) . . ?
N1 C10 C6 114.5(2) . . ?
N1 C10 H10A 106.3(16) . . ?
C6 C10 H10A 110.9(16) . . ?
N1 C10 H10B 105.7(15) . . ?
C6 C10 H10B 111.5(15) . . ?
H10A C10 H10B 108(2) . . ?
N1 C11 C12 112.4(2) . . ?
N1 C11 H11A 108.1(18) . . ?
C12 C11 H11A 110.1(17) . . ?
N1 C11 H11B 106.2(19) . . ?
C12 C11 H11B 111.4(18) . . ?
H11A C11 H11B 109(3) . . ?
C17 C12 C13 119.3(2) . . ?
C17 C12 C11 119.8(2) . . ?
C13 C12 C11 120.9(2) . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13 120.7(16) . . ?
C12 C13 H13 119.2(16) . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14 120(2) . . ?
C13 C14 H14 120(2) . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 H15 121(2) . . ?
C16 C15 H15 118(2) . . ?
C15 C16 C17 118.8(3) . . ?
C15 C16 C18 120.4(2) . . ?
C17 C16 C18 120.7(2) . . ?
C12 C17 C16 120.9(3) . . ?
C12 C17 H17 119.7(16) . . ?
C16 C17 H17 119.4(16) . . ?
N2 C18 C16 111.4(2) . . ?
N2 C18 H18A 106.7(17) . . ?
C16 C18 H18A 110.3(17) . . ?
N2 C18 H18B 105.0(19) . . ?
C16 C18 H18B 112.5(19) . . ?
H18A C18 H18B 111(3) . . ?
N2 C19 C20 113.8(2) . . ?
N2 C19 H19A 107.9(17) . . ?
C20 C19 H19A 110.8(18) . . ?
N2 C19 H19B 105.4(18) . . ?
C20 C19 H19B 109.8(17) . . ?
H19A C19 H19B 109(2) . . ?
C21 C20 C25 120.9(2) . . ?
C21 C20 C19 121.0(3) . . ?
C25 C20 C19 118.0(2) . . ?
C20 C21 C22 119.4(3) . . ?
C20 C21 C28 122.1(2) . . ?
C22 C21 C28 118.4(3) . . ?
C23 C22 C21 120.5(3) . . ?
C23 C22 C29 121.1(3) . . ?
C21 C22 C29 118.4(3) . . ?
C22 C23 C24 119.8(2) . . ?
C22 C23 C27 121.1(3) . . ?
C24 C23 C27 119.0(3) . . ?
C23 C24 C25 120.6(2) . . ?
C23 C24 C48 118.0(2) . . ?
C25 C24 C48 121.3(3) . . ?
C24 C25 C20 118.8(3) . . ?
C24 C25 C26 121.5(3) . . ?
C20 C25 C26 119.7(2) . . ?
C25 C26 H26A 116.9(19) . . ?
C25 C26 H26B 112(2) . . ?
H26A C26 H26B 104(3) . . ?
C25 C26 H26C 109(3) . . ?
H26A C26 H26C 100(3) . . ?
H26B C26 H26C 114(3) . . ?
C23 C27 H27A 114(3) . . ?
C23 C27 H27B 112(2) . . ?
H27A C27 H27B 113(3) . . ?
C23 C27 H27C 114(2) . . ?
H27A C27 H27C 103(3) . . ?
H27B C27 H27C 100(3) . . ?
C21 C28 H28A 113(3) . . ?
C21 C28 H28B 110(2) . . ?
H28A C28 H28B 108(3) . . ?
C21 C28 H28C 113(2) . . ?
H28A C28 H28C 103(3) . . ?
H28B C28 H28C 108(3) . . ?
N3 C29 C22 112.7(2) . . ?
N3 C29 H29A 106.5(17) . . ?
C22 C29 H29A 114.4(17) . . ?
N3 C29 H29B 105.2(19) . . ?
C22 C29 H29B 110.4(19) . . ?
H29A C29 H29B 107(2) . . ?
N3 C30 C31 111.6(2) . . ?
N3 C30 H30A 104.8(17) . . ?
C31 C30 H30A 111.4(17) . . ?
N3 C30 H30B 106.5(17) . . ?
C31 C30 H30B 111.7(17) . . ?
H30A C30 H30B 110(2) . . ?
C36 C31 C32 119.0(3) . . ?
C36 C31 C30 120.7(3) . . ?
C32 C31 C30 120.3(3) . . ?
C33 C32 C31 119.9(3) . . ?
C33 C32 H32 119(2) . . ?
C31 C32 H32 121(2) . . ?
C34 C33 C32 120.7(3) . . ?
C34 C33 H33 121(2) . . ?
C32 C33 H33 119(2) . . ?
C33 C34 C35 120.0(3) . . ?
C33 C34 H34 119.0(19) . . ?
C35 C34 H34 120.9(19) . . ?
C36 C35 C34 119.3(3) . . ?
C36 C35 C37 119.9(3) . . ?
C34 C35 C37 120.7(3) . . ?
C35 C36 C31 121.1(3) . . ?
C35 C36 H36 121(2) . . ?
C31 C36 H36 118(2) . . ?
N4 C37 C35 112.5(2) . . ?
N4 C37 H37A 105(2) . . ?
C35 C37 H37A 111(2) . . ?
N4 C37 H37B 107.0(17) . . ?
C35 C37 H37B 112.8(16) . . ?
H37A C37 H37B 109(3) . . ?
C4 C38 N4 114.6(2) . . ?
C4 C38 H38A 111.7(18) . . ?
N4 C38 H38A 104.4(17) . . ?
C4 C38 H38B 114.9(18) . . ?
N4 C38 H38B 102.5(17) . . ?
H38A C38 H38B 108(2) . . ?
N5 C39 C2 113.9(2) . . ?
N5 C39 H39A 106.0(16) . . ?
C2 C39 H39A 112.8(16) . . ?
N5 C39 H39B 106.6(19) . . ?
C2 C39 H39B 113.7(19) . . ?
H39A C39 H39B 103(2) . . ?
N5 C40 C41 111.5(2) . . ?
N5 C40 H40A 107.6(19) . . ?
C41 C40 H40A 113.0(18) . . ?
N5 C40 H40B 107(2) . . ?
C41 C40 H40B 109(2) . . ?
H40A C40 H40B 109(3) . . ?
C42 C41 C46 119.1(3) . . ?
C42 C41 C40 120.9(3) . . ?
C46 C41 C40 120.0(3) . . ?
C43 C42 C41 120.3(3) . . ?
C43 C42 H42 120.6(19) . . ?
C41 C42 H42 119.2(19) . . ?
C44 C43 C42 120.2(3) . . ?
C44 C43 H43 120.2(19) . . ?
C42 C43 H43 119.4(19) . . ?
C43 C44 C45 120.1(3) . . ?
C43 C44 H44 120(2) . . ?
C45 C44 H44 119(2) . . ?
C46 C45 C44 119.2(3) . . ?
C46 C45 C47 120.5(3) . . ?
C44 C45 C47 120.4(3) . . ?
C45 C46 C41 121.1(3) . . ?
C45 C46 H46 120.3(19) . . ?
C41 C46 H46 118.6(19) . . ?
N6 C47 C45 111.2(2) . . ?
N6 C47 H47A 106(2) . . ?
C45 C47 H47A 110(2) . . ?
N6 C47 H47B 108.0(17) . . ?
C45 C47 H47B 111.2(17) . . ?
H47A C47 H47B 110(3) . . ?
N6 C48 C24 112.4(2) . . ?
N6 C48 H48A 106.2(17) . . ?
C24 C48 H48A 111.7(17) . . ?
N6 C48 H48B 106.6(17) . . ?
C24 C48 H48B 114.6(17) . . ?
H48A C48 H48B 105(2) . . ?
C11 N1 C10 114.6(2) . . ?
C11 N1 H1A 106(2) . . ?
C10 N1 H1A 113(2) . . ?
C11 N1 H1B 108(2) . . ?
C10 N1 H1B 105(2) . . ?
H1A N1 H1B 110(3) . . ?
C18 N2 C19 115.0(2) . . ?
C18 N2 H2A 110(2) . . ?
C19 N2 H2A 112(2) . . ?
C18 N2 H2B 109.9(19) . . ?
C19 N2 H2B 106.9(19) . . ?
H2A N2 H2B 102(3) . . ?
C30 N3 C29 114.1(2) . . ?
C30 N3 H3A 105.3(19) . . ?
C29 N3 H3A 112(2) . . ?
C30 N3 H3B 110(2) . . ?
C29 N3 H3B 106(2) . . ?
H3A N3 H3B 110(3) . . ?
C37 N4 C38 115.0(2) . . ?
C37 N4 H4A 106(2) . . ?
C38 N4 H4A 111(2) . . ?
C37 N4 H4B 109(2) . . ?
C38 N4 H4B 104(2) . . ?
H4A N4 H4B 113(3) . . ?
C40 N5 C39 114.2(2) . . ?
C40 N5 H5A 109(2) . . ?
C39 N5 H5A 107(2) . . ?
C40 N5 H5B 108(2) . . ?
C39 N5 H5B 109(2) . . ?
H5A N5 H5B 110(3) . . ?
C47 N6 C48 114.2(2) . . ?
C47 N6 H6A 106(2) . . ?
C48 N6 H6A 109(2) . . ?
C47 N6 H6B 111(2) . . ?
C48 N6 H6B 105(2) . . ?
H6A N6 H6B 111(3) . . ?
H1C O1 H1D 105(4) . . ?
H2C O2 H2D 97(4) . . ?
H100 O3 H101 102(5) . . ?
H4C O4 H4D 108(4) . . ?
H6C O6 H6D 95(4) . . ?
H7D O7 H7E 112(4) . . ?
H8D O8 H8E 99(4) . . ?
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 1.403(4) . ?
C1 C2 1.411(4) . ?
C1 C7 1.510(4) . ?
C2 C3 1.406(4) . ?
C2 C39 1.508(4) . ?
C3 C4 1.405(4) . ?
C3 C8 1.511(4) . ?
C4 C5 1.418(4) . ?
C4 C38 1.507(4) . ?
C5 C6 1.403(4) . ?
C5 C9 1.504(4) . ?
C6 C10 1.517(4) . ?
C7 H7A 0.93(4) . ?
C7 H7B 0.96(4) . ?
C7 H7C 0.97(4) . ?
C8 H8A 0.94(5) . ?
C8 H8B 0.95(5) . ?
C8 H8C 0.97(5) . ?
C9 H9A 0.99(4) . ?
C9 H9B 0.90(4) . ?
C9 H9C 0.97(4) . ?
C10 N1 1.505(3) . ?
C10 H10A 0.95(3) . ?
C10 H10B 0.99(3) . ?
C11 N1 1.493(4) . ?
C11 C12 1.513(4) . ?
C11 H11A 0.93(3) . ?
C11 H11B 0.95(3) . ?
C12 C17 1.379(4) . ?
C12 C13 1.395(4) . ?
C13 C14 1.384(4) . ?
C13 H13 0.99(3) . ?
C14 C15 1.377(4) . ?
C14 H14 0.95(4) . ?
C15 C16 1.390(4) . ?
C15 H15 0.98(4) . ?
C16 C17 1.398(4) . ?
C16 C18 1.504(4) . ?
C17 H17 0.94(3) . ?
C18 N2 1.501(4) . ?
C18 H18A 0.99(3) . ?
C18 H18B 0.92(3) . ?
C19 N2 1.509(4) . ?
C19 C20 1.515(4) . ?
C19 H19A 0.99(3) . ?
C19 H19B 0.94(3) . ?
C20 C21 1.389(4) . ?
C20 C25 1.419(4) . ?
C21 C22 1.417(4) . ?
C21 C28 1.517(4) . ?
C22 C23 1.393(4) . ?
C22 C29 1.513(4) . ?
C23 C24 1.405(4) . ?
C23 C27 1.519(4) . ?
C24 C25 1.406(4) . ?
C24 C48 1.516(4) . ?
C25 C26 1.512(4) . ?
C26 H26A 0.97(4) . ?
C26 H26B 0.99(4) . ?
C26 H26C 0.91(4) . ?
C27 H27A 0.95(5) . ?
C27 H27B 0.97(4) . ?
C27 H27C 0.93(4) . ?
C28 H28A 0.90(4) . ?
C28 H28B 0.96(4) . ?
C28 H28C 0.97(4) . ?
C29 N3 1.511(4) . ?
C29 H29A 0.99(3) . ?
C29 H29B 0.91(3) . ?
C30 N3 1.503(3) . ?
C30 C31 1.504(4) . ?
C30 H30A 1.01(3) . ?
C30 H30B 0.96(3) . ?
C31 C36 1.392(4) . ?
C31 C32 1.397(4) . ?
C32 C33 1.384(4) . ?
C32 H32 0.97(3) . ?
C33 C34 1.382(4) . ?
C33 H33 0.93(3) . ?
C34 C35 1.391(4) . ?
C34 H34 0.95(3) . ?
C35 C36 1.388(4) . ?
C35 C37 1.501(4) . ?
C36 H36 0.92(4) . ?
C37 N4 1.497(4) . ?
C37 H37A 0.90(3) . ?
C37 H37B 1.02(3) . ?
C38 N4 1.511(4) . ?
C38 H38A 1.03(3) . ?
C38 H38B 0.97(3) . ?
C39 N5 1.502(4) . ?
C39 H39A 0.97(3) . ?
C39 H39B 1.00(3) . ?
C40 N5 1.497(4) . ?
C40 C41 1.500(4) . ?
C40 H40A 0.94(3) . ?
C40 H40B 0.96(4) . ?
C41 C42 1.389(4) . ?
C41 C46 1.390(4) . ?
C42 C43 1.387(4) . ?
C42 H42 0.92(3) . ?
C43 C44 1.383(4) . ?
C43 H43 0.93(3) . ?
C44 C45 1.395(4) . ?
C44 H44 0.96(3) . ?
C45 C46 1.385(4) . ?
C45 C47 1.502(4) . ?
C46 H46 0.90(3) . ?
C47 N6 1.499(4) . ?
C47 H47A 0.92(3) . ?
C47 H47B 0.98(3) . ?
C48 N6 1.511(3) . ?
C48 H48A 0.96(3) . ?
C48 H48B 0.97(3) . ?
N1 H1A 0.87(3) . ?
N1 H1B 0.86(4) . ?
N2 H2A 0.91(4) . ?
N2 H2B 0.93(3) . ?
N3 H3A 0.94(3) . ?
N3 H3B 0.89(3) . ?
N4 H4A 0.86(4) . ?
N4 H4B 0.87(3) . ?
N5 H5A 0.85(4) . ?
N5 H5B 0.93(4) . ?
N6 H6A 0.90(3) . ?
N6 H6B 0.92(4) . ?
O1 H1C 0.75(5) . ?
O1 H1D 0.83(5) . ?
O2 H2C 0.84(5) . ?
O2 H2D 0.86(5) . ?
O3 H100 0.66(4) . ?
O3 H101 0.93(6) . ?
O4 H4C 0.81(4) . ?
O4 H4D 0.85(4) . ?
O6 H6C 0.84(5) . ?
O6 H6D 0.97(5) . ?
O7 H7D 0.73(4) . ?
O7 H7E 0.83(5) . ?
O8 H8D 0.84(4) . ?
O8 H8E 0.69(4) . ?
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
N1 H1A O8 0.87(3) 1.88(3) 2.742(4) 167(3) 1
N1 H1B O3 0.86(4) 1.97(4) 2.773(4) 155(3) 2_545
O1 H1C Cl1 0.75(5) 2.45(5) 3.187(3) 168(5) 1
O1 H1D Cl3 0.83(5) 2.36(5) 3.168(3) 165(4) 1
N2 H2A Cl2 0.91(4) 2.23(4) 3.122(3) 166(3) 2_545
N2 H2B Cl6 0.93(3) 2.25(3) 3.074(3) 147(3) 2_545
O2 H2C Cl2 0.84(5) 2.27(5) 3.109(3) 170(4) 1
O2 H2D O1 0.86(5) 1.81(5) 2.654(3) 168(5) 1
N3 H3A O4 0.94(3) 1.81(4) 2.749(3) 171(3) 2_545
N3 H3B Cl4 0.89(3) 2.28(3) 3.115(3) 157(3) 3_666
N4 H4A Cl3 0.86(4) 2.36(4) 3.193(3) 164(3) 2_545
N4 H4B O6 0.87(3) 2.10(3) 2.827(4) 141(3) 1
O4 H4C O2 0.81(4) 1.97(4) 2.776(4) 170(4) 1
O4 H4D Cl3 0.85(4) 2.30(4) 3.126(2) 164(3) 1
N5 H5A Cl5 0.85(4) 2.28(4) 3.080(3) 156(3) 1_545
N5 H5B Cl1 0.93(4) 2.25(4) 3.149(3) 162(3) 2_545
N6 H6A O7 0.90(3) 1.88(3) 2.762(4) 169(3) 1
N6 H6B Cl5 0.92(4) 2.22(4) 3.129(3) 166(3) 3_666
O6 H6C Cl6 0.84(5) 2.42(5) 3.229(3) 162(4) 1
O6 H6D O9 0.97(5) 1.84(5) 2.800(4) 171(4) 1
O7 H7D O2 0.73(4) 2.02(4) 2.750(4) 170(4) 2_545
O7 H7E Cl1 0.83(5) 2.35(5) 3.144(2) 162(4) 2_545
O8 H8D Cl3 0.84(4) 2.35(5) 3.180(3) 170(4) 1_545
O8 H8E Cl2 0.69(4) 2.49(4) 3.169(3) 166(5) 2_545
O3 H100 Cl1 0.66(4) 2.53(4) 3.181(3) 171(5) 4_676
O3 H101 O5 0.93(6) 1.78(6) 2.711(4) 176(5) 1
