#------------------------------------------------------------------------------
#$Date: 2016-03-24 17:20:36 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179686 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/08/7000874.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_7000874
loop_
_publ_author_name
'Ehrhart, Jérôme'
'Planeix, Jean-Marc'
'Kyritsakas-Gruber, Nathalie'
'Hosseini, Mir Wais'
_publ_section_title
;
 Synthesis and structural studies of metallamacrotricycles based on a
 metacyclophane in 1,3-alternate conformation bearing four imidazolyl
 units
;
_journal_issue                   14
_journal_name_full               'Dalton Transactions'
_journal_page_first              2552
_journal_page_last               2557
_journal_paper_doi               10.1039/b816053h
_journal_year                    2009
_chemical_formula_moiety         'C56 H64 N8, 1.5(C2 H4 Cl2), 3(H2 O)'
_chemical_formula_sum            'C59 H76 Cl3 N8 O3'
_chemical_formula_weight         1051.63
_chemical_name_systematic
;
?
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.773(2)
_cell_angle_beta                 94.242(3)
_cell_angle_gamma                94.968(3)
_cell_formula_units_Z            2
_cell_length_a                   11.8093(4)
_cell_length_b                   14.6475(6)
_cell_length_c                   16.0027(7)
_cell_measurement_reflns_used    1776
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.000
_cell_measurement_theta_min      2.11
_cell_volume                     2677.07(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0637
_diffrn_reflns_av_sigmaI/netI    0.1127
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24992
_diffrn_reflns_theta_full        27.55
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.31
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.9778
_exptl_absorpt_correction_T_min  0.9649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1122
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.878
_refine_diff_density_min         -0.662
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       0.0060(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     671
_refine_ls_number_reflns         11183
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1938
_refine_ls_R_factor_gt           0.0966
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1741P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2606
_refine_ls_wR_factor_ref         0.3407
_reflns_number_gt                4697
_reflns_number_total             11183
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b816053h.txt
_cod_data_source_block           4
_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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        2677.07(18)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7000874
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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
C1 C 0.6983(4) 0.4474(4) 0.0451(3) 0.0347(12) Uani 1 1 d . . .
C2 C 0.6509(4) 0.4612(4) -0.0337(3) 0.0354(12) Uani 1 1 d . . .
C3 C 0.5520(4) 0.4049(4) -0.0758(3) 0.0369(12) Uani 1 1 d . . .
C4 C 0.4989(4) 0.3352(4) -0.0397(3) 0.0367(12) Uani 1 1 d . . .
C5 C 0.5439(4) 0.3216(3) 0.0393(3) 0.0337(12) Uani 1 1 d . . .
C6 C 0.6430(4) 0.3790(4) 0.0828(3) 0.0337(11) Uani 1 1 d . . .
C7 C 0.7042(5) 0.5389(4) -0.0719(3) 0.0408(13) Uani 1 1 d . . .
H7A H 0.7693 0.5171 -0.1023 0.061 Uiso 1 1 calc R . .
H7B H 0.7303 0.5945 -0.0257 0.061 Uiso 1 1 calc R . .
H7C H 0.6473 0.5554 -0.1123 0.061 Uiso 1 1 calc R . .
C8 C 0.5042(4) 0.4196(4) -0.1607(3) 0.0442(14) Uani 1 1 d . . .
H8A H 0.4303 0.3802 -0.1788 0.053 Uiso 1 1 calc R . .
H8B H 0.4898 0.4863 -0.1541 0.053 Uiso 1 1 calc R . .
N1 N 0.5825(4) 0.3953(3) -0.2275(3) 0.0454(12) Uani 1 1 d . . .
C9 C 0.6765(5) 0.3495(5) -0.2268(4) 0.0566(17) Uani 1 1 d . . .
H9 H 0.7059 0.3231 -0.1816 0.068 Uiso 1 1 calc R . .
C10 C 0.7213(6) 0.3482(5) -0.3022(5) 0.0651(19) Uani 1 1 d . . .
H10 H 0.7866 0.3182 -0.3198 0.078 Uiso 1 1 calc R . .
N2 N 0.6590(6) 0.3957(6) -0.3485(4) 0.091(2) Uani 1 1 d . . .
C11 C 0.5776(7) 0.4231(7) -0.3009(5) 0.084(3) Uani 1 1 d . . .
H11 H 0.5205 0.4593 -0.3172 0.101 Uiso 1 1 calc R . .
C12 C 0.3925(4) 0.2771(4) -0.0895(4) 0.0431(13) Uani 1 1 d . . .
H12A H 0.3603 0.2349 -0.0555 0.065 Uiso 1 1 calc R . .
H12B H 0.4124 0.2397 -0.1441 0.065 Uiso 1 1 calc R . .
H12C H 0.3360 0.3191 -0.1010 0.065 Uiso 1 1 calc R . .
C13 C 0.6833(4) 0.3724(4) 0.1721(3) 0.0398(13) Uani 1 1 d . . .
H13A H 0.6174 0.3581 0.2025 0.060 Uiso 1 1 calc R . .
H13B H 0.7251 0.4325 0.2031 0.060 Uiso 1 1 calc R . .
H13C H 0.7338 0.3223 0.1690 0.060 Uiso 1 1 calc R . .
C14 C 0.4842(4) 0.2498(4) 0.0834(3) 0.0356(12) Uani 1 1 d . . .
H14A H 0.4543 0.2854 0.1357 0.043 Uiso 1 1 calc R . .
H14B H 0.4177 0.2161 0.0441 0.043 Uiso 1 1 calc R . .
C15 C 0.5547(4) 0.1761(3) 0.1097(3) 0.0309(11) Uani 1 1 d . . .
C16 C 0.5611(4) 0.1636(4) 0.1945(3) 0.0345(12) Uani 1 1 d . . .
C17 C 0.6267(4) 0.0958(4) 0.2166(3) 0.0340(12) Uani 1 1 d . . .
C18 C 0.6877(4) 0.0411(3) 0.1561(3) 0.0313(11) Uani 1 1 d . . .
C19 C 0.6825(4) 0.0530(3) 0.0712(3) 0.0313(11) Uani 1 1 d . . .
C20 C 0.6113(4) 0.1180(3) 0.0471(3) 0.0327(12) Uani 1 1 d . . .
C21 C 0.4962(5) 0.2198(4) 0.2629(3) 0.0429(14) Uani 1 1 d . . .
H21A H 0.4685 0.1796 0.3002 0.064 Uiso 1 1 calc R . .
H21B H 0.4312 0.2429 0.2353 0.064 Uiso 1 1 calc R . .
H21C H 0.5470 0.2735 0.2976 0.064 Uiso 1 1 calc R . .
C22 C 0.6359(4) 0.0851(4) 0.3090(3) 0.0393(13) Uani 1 1 d . . .
H22A H 0.7086 0.0595 0.3211 0.047 Uiso 1 1 calc R . .
H22B H 0.6379 0.1480 0.3481 0.047 Uiso 1 1 calc R . .
N3 N 0.5412(3) 0.0232(3) 0.3270(3) 0.0359(10) Uani 1 1 d . . .
C23 C 0.4805(5) 0.0415(4) 0.3958(4) 0.0495(16) Uani 1 1 d . . .
H23 H 0.4919 0.0985 0.4389 0.059 Uiso 1 1 calc R . .
N4 N 0.4030(4) -0.0296(4) 0.3960(3) 0.0497(13) Uani 1 1 d . . .
C24 C 0.4179(5) -0.0978(4) 0.3250(4) 0.0483(15) Uani 1 1 d . . .
H24 H 0.3757 -0.1583 0.3084 0.058 Uiso 1 1 calc R . .
C25 C 0.5011(5) -0.0663(4) 0.2823(4) 0.0458(14) Uani 1 1 d . . .
H25 H 0.5272 -0.0998 0.2307 0.055 Uiso 1 1 calc R . .
C26 C 0.7557(4) -0.0345(4) 0.1807(3) 0.0392(13) Uani 1 1 d . . .
H26A H 0.8370 -0.0111 0.1910 0.059 Uiso 1 1 calc R . .
H26B H 0.7445 -0.0911 0.1338 0.059 Uiso 1 1 calc R . .
H26C H 0.7294 -0.0498 0.2331 0.059 Uiso 1 1 calc R . .
C27 C 0.5925(4) 0.1209(4) -0.0455(3) 0.0401(13) Uani 1 1 d . . .
H27A H 0.5182 0.1432 -0.0564 0.060 Uiso 1 1 calc R . .
H27B H 0.5940 0.0575 -0.0815 0.060 Uiso 1 1 calc R . .
H27C H 0.6530 0.1637 -0.0593 0.060 Uiso 1 1 calc R . .
C28 C 0.7489(4) -0.0032(3) 0.0034(3) 0.0335(11) Uani 1 1 d . . .
H28A H 0.6931 -0.0456 -0.0404 0.040 Uiso 1 1 calc R . .
H28B H 0.7948 -0.0435 0.0314 0.040 Uiso 1 1 calc R . .
C29 C 0.8287(4) 0.0513(3) -0.0433(3) 0.0285(11) Uani 1 1 d . . .
C30 C 0.8197(4) 0.0325(3) -0.1331(3) 0.0315(11) Uani 1 1 d . . .
C31 C 0.8931(4) 0.0852(3) -0.1741(3) 0.0320(11) Uani 1 1 d . . .
C32 C 0.9775(4) 0.1564(4) -0.1263(3) 0.0340(12) Uani 1 1 d . . .
C33 C 0.9858(4) 0.1745(3) -0.0363(3) 0.0319(11) Uani 1 1 d . . .
C34 C 0.9142(4) 0.1189(3) 0.0053(3) 0.0330(11) Uani 1 1 d . . .
C35 C 0.7346(4) -0.0458(4) -0.1870(3) 0.0426(13) Uani 1 1 d . . .
H35A H 0.6620 -0.0207 -0.1980 0.064 Uiso 1 1 calc R . .
H35B H 0.7221 -0.0959 -0.1560 0.064 Uiso 1 1 calc R . .
H35C H 0.7646 -0.0713 -0.2419 0.064 Uiso 1 1 calc R . .
C36 C 0.8795(4) 0.0718(4) -0.2714(3) 0.0379(12) Uani 1 1 d . . .
H36A H 0.8002 0.0449 -0.2932 0.046 Uiso 1 1 calc R . .
H36B H 0.8919 0.1340 -0.2857 0.046 Uiso 1 1 calc R . .
N5 N 0.9598(3) 0.0090(3) -0.3159(3) 0.0344(10) Uani 1 1 d . . .
C37 C 1.0272(5) 0.0300(4) -0.3749(3) 0.0439(14) Uani 1 1 d . . .
H37 H 1.0310 0.0877 -0.3929 0.053 Uiso 1 1 calc R . .
N6 N 1.0881(4) -0.0413(3) -0.4049(3) 0.0473(12) Uani 1 1 d . . .
C38 C 1.0543(5) -0.1093(4) -0.3634(4) 0.0452(14) Uani 1 1 d . . .
H38 H 1.0818 -0.1694 -0.3722 0.054 Uiso 1 1 calc R . .
C39 C 0.9760(5) -0.0802(4) -0.3077(3) 0.0399(13) Uani 1 1 d . . .
H39 H 0.9402 -0.1143 -0.2711 0.048 Uiso 1 1 calc R . .
C40 C 1.0546(4) 0.2099(4) -0.1748(3) 0.0401(13) Uani 1 1 d . . .
H40A H 1.0108 0.2526 -0.2000 0.060 Uiso 1 1 calc R . .
H40B H 1.0848 0.1652 -0.2206 0.060 Uiso 1 1 calc R . .
H40C H 1.1180 0.2463 -0.1350 0.060 Uiso 1 1 calc R . .
C41 C 0.9345(4) 0.1297(4) 0.1005(3) 0.0404(13) Uani 1 1 d . . .
H41A H 0.8829 0.1725 0.1296 0.061 Uiso 1 1 calc R . .
H41B H 1.0139 0.1554 0.1200 0.061 Uiso 1 1 calc R . .
H41C H 0.9201 0.0680 0.1144 0.061 Uiso 1 1 calc R . .
C42 C 1.0737(4) 0.2523(4) 0.0194(3) 0.0341(11) Uani 1 1 d . . .
H42A H 1.1301 0.2213 0.0493 0.041 Uiso 1 1 calc R . .
H42B H 1.1151 0.2836 -0.0199 0.041 Uiso 1 1 calc R . .
C43 C 1.0301(4) 0.3290(4) 0.0872(3) 0.0340(12) Uani 1 1 d . . .
C44 C 1.0779(4) 0.3524(4) 0.1729(3) 0.0369(12) Uani 1 1 d . . .
C45 C 1.0400(4) 0.4270(4) 0.2320(3) 0.0382(13) Uani 1 1 d . . .
C46 C 0.9524(4) 0.4773(4) 0.2062(3) 0.0367(12) Uani 1 1 d . . .
C47 C 0.9049(4) 0.4532(3) 0.1209(3) 0.0319(11) Uani 1 1 d . . .
C48 C 0.9458(4) 0.3814(4) 0.0605(3) 0.0341(12) Uani 1 1 d . . .
C49 C 1.1711(4) 0.3021(4) 0.2055(3) 0.0449(14) Uani 1 1 d . . .
H49A H 1.1886 0.2511 0.1589 0.067 Uiso 1 1 calc R . .
H49B H 1.1459 0.2758 0.2531 0.067 Uiso 1 1 calc R . .
H49C H 1.2396 0.3465 0.2259 0.067 Uiso 1 1 calc R . .
C50 C 1.0912(5) 0.4528(4) 0.3250(3) 0.0435(14) Uani 1 1 d . . .
H50A H 1.1701 0.4351 0.3278 0.052 Uiso 1 1 calc R . .
H50B H 1.0950 0.5219 0.3468 0.052 Uiso 1 1 calc R . .
N7 N 1.0249(4) 0.4060(3) 0.3809(3) 0.0410(11) Uani 1 1 d . . .
C51 C 1.0603(5) 0.3971(4) 0.4585(3) 0.0492(15) Uani 1 1 d . . .
H51 H 1.1368 0.4151 0.4834 0.059 Uiso 1 1 calc R . .
N8 N 0.9801(4) 0.3610(3) 0.4986(3) 0.0495(13) Uani 1 1 d . . .
C52 C 0.8834(5) 0.3493(4) 0.4427(4) 0.0521(16) Uani 1 1 d . . .
H52 H 0.8094 0.3265 0.4534 0.063 Uiso 1 1 calc R . .
C53 C 0.9099(5) 0.3753(4) 0.3696(4) 0.0497(15) Uani 1 1 d . . .
H53 H 0.8590 0.3728 0.3201 0.060 Uiso 1 1 calc R . .
C54 C 0.9144(5) 0.5581(4) 0.2708(4) 0.0457(14) Uani 1 1 d . . .
H54A H 0.9536 0.6176 0.2643 0.069 Uiso 1 1 calc R . .
H54B H 0.9333 0.5501 0.3292 0.069 Uiso 1 1 calc R . .
H54C H 0.8317 0.5590 0.2605 0.069 Uiso 1 1 calc R . .
C55 C 0.9039(5) 0.3659(4) -0.0327(3) 0.0403(13) Uani 1 1 d . . .
H55A H 0.9641 0.3427 -0.0682 0.060 Uiso 1 1 calc R . .
H55B H 0.8837 0.4254 -0.0450 0.060 Uiso 1 1 calc R . .
H55C H 0.8364 0.3194 -0.0460 0.060 Uiso 1 1 calc R . .
C56 C 0.8084(4) 0.5062(4) 0.0907(3) 0.0376(12) Uani 1 1 d . . .
H56A H 0.7879 0.5514 0.1417 0.045 Uiso 1 1 calc R . .
H56B H 0.8393 0.5434 0.0513 0.045 Uiso 1 1 calc R . .
C57 C 0.2271(8) 0.1780(10) 0.5042(7) 0.157(6) Uani 1 1 d . . .
H57A H 0.1590 0.2084 0.5238 0.188 Uiso 1 1 calc R . .
H57B H 0.2016 0.1111 0.4769 0.188 Uiso 1 1 calc R . .
C58 C 0.3119(11) 0.1822(13) 0.5838(8) 0.209(9) Uani 1 1 d . . .
H58A H 0.3114 0.1179 0.5940 0.250 Uiso 1 1 calc R . .
H58B H 0.3895 0.2009 0.5698 0.250 Uiso 1 1 calc R . .
Cl1 Cl 0.28159(18) 0.23139(17) 0.42757(15) 0.0913(7) Uani 1 1 d . . .
Cl2 Cl 0.2903(3) 0.2476(3) 0.6662(2) 0.1728(16) Uani 1 1 d . . .
C59 C 0.5437(10) 0.5335(8) 0.5093(7) 0.165(6) Uani 1 1 d D . .
H59A H 0.5818 0.5395 0.5678 0.198 Uiso 1 1 calc R . .
H59B H 0.5206 0.5952 0.5032 0.198 Uiso 1 1 calc R . .
Cl3 Cl 0.63869(18) 0.48070(19) 0.41989(16) 0.0978(8) Uani 1 1 d D . .
O1 O 0.9463(4) 0.2374(3) 0.6118(2) 0.0565(11) Uani 1 1 d . . .
O2 O 0.7610(3) 0.1119(3) 0.5208(2) 0.0535(11) Uani 1 1 d . . .
O3 O 0.6203(5) 0.2493(4) 0.4910(3) 0.0856(16) Uani 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'
Cl Cl 0.1484 0.1585 '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'
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
C2 C1 C6 119.4(4) . . ?
C2 C1 C56 120.6(4) . . ?
C6 C1 C56 120.0(5) . . ?
C1 C2 C3 119.9(4) . . ?
C1 C2 C7 120.1(4) . . ?
C3 C2 C7 120.0(5) . . ?
C4 C3 C2 120.8(5) . . ?
C4 C3 C8 120.3(5) . . ?
C2 C3 C8 118.9(5) . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 C12 122.4(5) . . ?
C3 C4 C12 117.5(5) . . ?
C4 C5 C6 119.5(4) . . ?
C4 C5 C14 121.6(4) . . ?
C6 C5 C14 118.8(5) . . ?
C1 C6 C5 120.3(5) . . ?
C1 C6 C13 120.0(4) . . ?
C5 C6 C13 119.5(4) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C3 111.6(4) . . ?
N1 C8 H8A 109.3 . . ?
C3 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
C3 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C11 N1 C9 105.3(5) . . ?
C11 N1 C8 124.5(6) . . ?
C9 N1 C8 130.0(5) . . ?
N1 C9 C10 107.3(6) . . ?
N1 C9 H9 126.4 . . ?
C10 C9 H9 126.4 . . ?
N2 C10 C9 109.5(7) . . ?
N2 C10 H10 125.3 . . ?
C9 C10 H10 125.3 . . ?
C11 N2 C10 104.5(6) . . ?
N2 C11 N1 113.4(7) . . ?
N2 C11 H11 123.3 . . ?
N1 C11 H11 123.3 . . ?
C4 C12 H12A 109.5 . . ?
C4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C13 H13A 109.5 . . ?
C6 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C6 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C5 117.9(4) . . ?
C15 C14 H14A 107.8 . . ?
C5 C14 H14A 107.8 . . ?
C15 C14 H14B 107.8 . . ?
C5 C14 H14B 107.8 . . ?
H14A C14 H14B 107.2 . . ?
C16 C15 C20 119.7(5) . . ?
C16 C15 C14 121.0(4) . . ?
C20 C15 C14 119.3(4) . . ?
C17 C16 C15 119.6(5) . . ?
C17 C16 C21 118.5(4) . . ?
C15 C16 C21 121.9(5) . . ?
C16 C17 C18 121.2(4) . . ?
C16 C17 C22 119.1(4) . . ?
C18 C17 C22 119.7(5) . . ?
C17 C18 C19 119.9(5) . . ?
C17 C18 C26 120.4(4) . . ?
C19 C18 C26 119.7(4) . . ?
C18 C19 C20 119.3(4) . . ?
C18 C19 C28 122.1(5) . . ?
C20 C19 C28 118.6(4) . . ?
C15 C20 C19 120.1(4) . . ?
C15 C20 C27 120.5(5) . . ?
C19 C20 C27 119.3(4) . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C22 C17 112.9(4) . . ?
N3 C22 H22A 109.0 . . ?
C17 C22 H22A 109.0 . . ?
N3 C22 H22B 109.0 . . ?
C17 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
C23 N3 C25 106.0(4) . . ?
C23 N3 C22 125.8(4) . . ?
C25 N3 C22 128.1(4) . . ?
N4 C23 N3 111.8(5) . . ?
N4 C23 H23 124.1 . . ?
N3 C23 H23 124.1 . . ?
C23 N4 C24 105.1(4) . . ?
C25 C24 N4 109.8(5) . . ?
C25 C24 H24 125.1 . . ?
N4 C24 H24 125.1 . . ?
C24 C25 N3 107.3(5) . . ?
C24 C25 H25 126.4 . . ?
N3 C25 H25 126.4 . . ?
C18 C26 H26A 109.5 . . ?
C18 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C18 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C20 C27 H27A 109.5 . . ?
C20 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C20 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C19 C28 C29 117.8(4) . . ?
C19 C28 H28A 107.9 . . ?
C29 C28 H28A 107.9 . . ?
C19 C28 H28B 107.9 . . ?
C29 C28 H28B 107.9 . . ?
H28A C28 H28B 107.2 . . ?
C30 C29 C34 120.3(4) . . ?
C30 C29 C28 120.7(4) . . ?
C34 C29 C28 119.0(4) . . ?
C29 C30 C31 119.3(4) . . ?
C29 C30 C35 121.2(4) . . ?
C31 C30 C35 119.5(4) . . ?
C30 C31 C32 121.4(4) . . ?
C30 C31 C36 120.6(4) . . ?
C32 C31 C36 117.9(4) . . ?
C33 C32 C31 118.7(4) . . ?
C33 C32 C40 122.6(4) . . ?
C31 C32 C40 118.7(4) . . ?
C32 C33 C34 119.8(4) . . ?
C32 C33 C42 121.3(4) . . ?
C34 C33 C42 118.9(4) . . ?
C29 C34 C33 120.2(4) . . ?
C29 C34 C41 120.3(4) . . ?
C33 C34 C41 119.4(4) . . ?
C30 C35 H35A 109.5 . . ?
C30 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C30 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N5 C36 C31 113.3(4) . . ?
N5 C36 H36A 108.9 . . ?
C31 C36 H36A 108.9 . . ?
N5 C36 H36B 108.9 . . ?
C31 C36 H36B 108.9 . . ?
H36A C36 H36B 107.7 . . ?
C37 N5 C39 107.8(4) . . ?
C37 N5 C36 124.9(5) . . ?
C39 N5 C36 127.2(4) . . ?
N6 C37 N5 111.1(5) . . ?
N6 C37 H37 124.4 . . ?
N5 C37 H37 124.4 . . ?
C37 N6 C38 104.5(4) . . ?
N6 C38 C39 111.4(5) . . ?
N6 C38 H38 124.3 . . ?
C39 C38 H38 124.3 . . ?
C38 C39 N5 105.1(5) . . ?
C38 C39 H39 127.4 . . ?
N5 C39 H39 127.4 . . ?
C32 C40 H40A 109.5 . . ?
C32 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C32 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C34 C41 H41A 109.5 . . ?
C34 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C34 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C43 C42 C33 118.3(4) . . ?
C43 C42 H42A 107.7 . . ?
C33 C42 H42A 107.7 . . ?
C43 C42 H42B 107.7 . . ?
C33 C42 H42B 107.7 . . ?
H42A C42 H42B 107.1 . . ?
C44 C43 C48 119.6(5) . . ?
C44 C43 C42 121.7(5) . . ?
C48 C43 C42 118.5(5) . . ?
C43 C44 C45 119.9(5) . . ?
C43 C44 C49 122.8(5) . . ?
C45 C44 C49 117.3(5) . . ?
C44 C45 C46 120.6(5) . . ?
C44 C45 C50 120.3(5) . . ?
C46 C45 C50 119.1(5) . . ?
C47 C46 C45 119.2(5) . . ?
C47 C46 C54 121.3(5) . . ?
C45 C46 C54 119.5(5) . . ?
C46 C47 C48 120.6(5) . . ?
C46 C47 C56 120.5(5) . . ?
C48 C47 C56 118.9(4) . . ?
C47 C48 C43 120.0(5) . . ?
C47 C48 C55 119.3(5) . . ?
C43 C48 C55 120.6(5) . . ?
C44 C49 H49A 109.5 . . ?
C44 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C44 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
N7 C50 C45 112.6(4) . . ?
N7 C50 H50A 109.1 . . ?
C45 C50 H50A 109.1 . . ?
N7 C50 H50B 109.1 . . ?
C45 C50 H50B 109.1 . . ?
H50A C50 H50B 107.8 . . ?
C51 N7 C53 105.5(5) . . ?
C51 N7 C50 126.2(5) . . ?
C53 N7 C50 127.7(5) . . ?
N8 C51 N7 114.0(5) . . ?
N8 C51 H51 123.0 . . ?
N7 C51 H51 123.0 . . ?
C51 N8 C52 104.2(5) . . ?
C53 C52 N8 109.4(5) . . ?
C53 C52 H52 125.3 . . ?
N8 C52 H52 125.3 . . ?
C52 C53 N7 106.9(5) . . ?
C52 C53 H53 126.6 . . ?
N7 C53 H53 126.6 . . ?
C46 C54 H54A 109.5 . . ?
C46 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C46 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C48 C55 H55A 109.5 . . ?
C48 C55 H55B 109.5 . . ?
H55A C55 H55B 109.5 . . ?
C48 C55 H55C 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
C1 C56 C47 117.5(4) . . ?
C1 C56 H56A 107.9 . . ?
C47 C56 H56A 107.9 . . ?
C1 C56 H56B 107.9 . . ?
C47 C56 H56B 107.9 . . ?
H56A C56 H56B 107.2 . . ?
C58 C57 Cl1 114.6(8) . . ?
C58 C57 H57A 108.6 . . ?
Cl1 C57 H57A 108.6 . . ?
C58 C57 H57B 108.6 . . ?
Cl1 C57 H57B 108.6 . . ?
H57A C57 H57B 107.6 . . ?
Cl2 C58 C57 116.6(10) . . ?
Cl2 C58 H58A 108.1 . . ?
C57 C58 H58A 108.1 . . ?
Cl2 C58 H58B 108.1 . . ?
C57 C58 H58B 108.1 . . ?
H58A C58 H58B 107.3 . . ?
C59 C59 Cl3 98.7(12) 2_666 . ?
C59 C59 H59A 112.0 2_666 . ?
Cl3 C59 H59A 112.0 . . ?
C59 C59 H59B 112.0 2_666 . ?
Cl3 C59 H59B 112.0 . . ?
H59A C59 H59B 109.7 . . ?
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 C2 1.404(7) . ?
C1 C6 1.416(6) . ?
C1 C56 1.534(7) . ?
C2 C3 1.403(7) . ?
C2 C7 1.519(7) . ?
C3 C4 1.405(7) . ?
C3 C8 1.500(7) . ?
C4 C5 1.396(7) . ?
C4 C12 1.518(7) . ?
C5 C6 1.418(7) . ?
C5 C14 1.540(6) . ?
C6 C13 1.499(7) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 N1 1.470(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
N1 C11 1.324(8) . ?
N1 C9 1.347(8) . ?
C9 C10 1.349(9) . ?
C9 H9 0.9500 . ?
C10 N2 1.347(9) . ?
C10 H10 0.9500 . ?
N2 C11 1.306(9) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.530(7) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.407(7) . ?
C15 C20 1.413(7) . ?
C16 C17 1.400(7) . ?
C16 C21 1.516(7) . ?
C17 C18 1.400(7) . ?
C17 C22 1.517(7) . ?
C18 C19 1.405(6) . ?
C18 C26 1.525(7) . ?
C19 C20 1.420(7) . ?
C19 C28 1.521(7) . ?
C20 C27 1.491(7) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 N3 1.465(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
N3 C23 1.347(6) . ?
N3 C25 1.373(7) . ?
C23 N4 1.327(7) . ?
C23 H23 0.9500 . ?
N4 C24 1.370(7) . ?
C24 C25 1.343(7) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C29 1.525(6) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.395(6) . ?
C29 C34 1.405(6) . ?
C30 C31 1.404(6) . ?
C30 C35 1.519(7) . ?
C31 C32 1.422(7) . ?
C31 C36 1.519(7) . ?
C32 C33 1.401(7) . ?
C32 C40 1.514(6) . ?
C33 C34 1.422(6) . ?
C33 C42 1.541(6) . ?
C34 C41 1.497(7) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 N5 1.488(6) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
N5 C37 1.347(6) . ?
N5 C39 1.369(7) . ?
C37 N6 1.340(7) . ?
C37 H37 0.9500 . ?
N6 C38 1.363(7) . ?
C38 C39 1.361(7) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 C43 1.532(7) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.401(7) . ?
C43 C48 1.407(7) . ?
C44 C45 1.407(8) . ?
C44 C49 1.500(7) . ?
C45 C46 1.409(8) . ?
C45 C50 1.517(7) . ?
C46 C47 1.394(7) . ?
C46 C54 1.513(7) . ?
C47 C48 1.407(7) . ?
C47 C56 1.540(7) . ?
C48 C55 1.498(7) . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 N7 1.471(6) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
N7 C51 1.319(6) . ?
N7 C53 1.378(7) . ?
C51 N8 1.320(7) . ?
C51 H51 0.9500 . ?
N8 C52 1.371(7) . ?
C52 C53 1.356(8) . ?
C52 H52 0.9500 . ?
C53 H53 0.9500 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C55 H55A 0.9800 . ?
C55 H55B 0.9800 . ?
C55 H55C 0.9800 . ?
C56 H56A 0.9900 . ?
C56 H56B 0.9900 . ?
C57 C58 1.548(15) . ?
C57 Cl1 1.728(9) . ?
C57 H57A 0.9900 . ?
C57 H57B 0.9900 . ?
C58 Cl2 1.501(13) . ?
C58 H58A 0.9900 . ?
C58 H58B 0.9900 . ?
C59 C59 1.329(19) 2_666 ?
C59 Cl3 1.950(12) . ?
C59 H59A 0.9900 . ?
C59 H59B 0.9900 . ?
