#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:45:47 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180314 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/28/7152896.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_7152896
loop_
_publ_author_name
'Guchhait, Tapas'
'Jha, Vikesh Kumar'
'Mani, Ganesan'
_publ_section_title
;
 The syn and anti isomers of the porphyrinogen-like precursor of
 calix[4]phyrin: isolation, X-ray structure, anion binding and
 fluoride-ion-mediated proton-deuterium exchange studies.
;
_journal_issue                   17
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2818
_journal_page_last               2826
_journal_paper_doi               10.1039/c3ob40147b
_journal_volume                  11
_journal_year                    2013
_chemical_formula_sum            'C38 H43.33 N6 O0.66'
_chemical_formula_weight         594.68
_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                97.519(6)
_cell_angle_beta                 104.854(6)
_cell_angle_gamma                111.281(5)
_cell_formula_units_Z            3
_cell_length_a                   11.774(2)
_cell_length_b                   13.988(3)
_cell_length_c                   17.936(3)
_cell_measurement_reflns_used    31096
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.76
_cell_volume                     2577.0(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker-APEX-II CCD area detector'
_diffrn_measurement_method       hemisphere
_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  0.0614
_diffrn_reflns_av_sigmaI/netI    0.0693
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            31096
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.9944
_exptl_absorpt_correction_T_min  0.9792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             956
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     628
_refine_ls_number_reflns         9037
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1194
_refine_ls_R_factor_gt           0.0530
_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)+(0.0631P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1475
_reflns_number_gt                4643
_reflns_number_total             9037
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c3ob40147b.txt
_cod_data_source_block           antiiso
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        2577.1(8)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7152896
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
C1 C 0.6684(2) 0.33175(19) 0.51031(14) 0.0496(6) Uani 1 1 d .
C2 C 0.5488(3) 0.2658(2) 0.50555(19) 0.0776(9) Uani 1 1 d .
H2 H 0.4878 0.2864 0.5181 0.093 Uiso 1 1 calc R
C3 C 0.5311(3) 0.1601(2) 0.47845(18) 0.0789(9) Uani 1 1 d .
H3 H 0.4566 0.0996 0.4695 0.095 Uiso 1 1 calc R
C4 C 0.6417(2) 0.16263(19) 0.46789(14) 0.0533(7) Uani 1 1 d .
C5 C 0.6788(2) 0.07376(18) 0.44575(15) 0.0580(7) Uani 1 1 d .
H5 H 0.5986 0.0090 0.4264 0.070 Uiso 1 1 calc R
C6 C 0.7351(3) 0.0806(2) 0.37853(15) 0.0580(7) Uani 1 1 d .
C7 C 0.6832(3) -0.0021(2) 0.31191(18) 0.0800(9) Uani 1 1 d .
H7 H 0.6112 -0.0628 0.3068 0.096 Uiso 1 1 calc R
C8 C 0.7386(4) 0.0057(3) 0.2530(2) 0.0962(11) Uani 1 1 d .
H8 H 0.7050 -0.0497 0.2077 0.115 Uiso 1 1 calc R
C9 C 0.8430(4) 0.0952(3) 0.26189(19) 0.0879(10) Uani 1 1 d .
H9 H 0.8822 0.1025 0.2228 0.106 Uiso 1 1 calc R
C10 C 0.8895(3) 0.1747(2) 0.3295(2) 0.0821(9) Uani 1 1 d .
H10 H 0.9609 0.2361 0.3350 0.099 Uiso 1 1 calc R
C11 C 0.7659(2) 0.05839(17) 0.51643(15) 0.0523(7) Uani 1 1 d .
C12 C 0.8513(3) 0.01298(19) 0.52164(16) 0.0642(8) Uani 1 1 d .
H12 H 0.8750 -0.0114 0.4799 0.077 Uiso 1 1 calc R
C13 C 0.8975(3) 0.00948(19) 0.60142(17) 0.0641(7) Uani 1 1 d .
H13 H 0.9569 -0.0179 0.6212 0.077 Uiso 1 1 calc R
C14 C 0.8406(2) 0.05291(18) 0.64481(15) 0.0525(6) Uani 1 1 d .
C15 C 0.8474(2) 0.06775(19) 0.73114(15) 0.0569(7) Uani 1 1 d .
C16 C 0.7261(3) -0.0192(2) 0.73760(17) 0.0769(9) Uani 1 1 d .
H16A H 0.7271 -0.0052 0.7922 0.092 Uiso 1 1 calc R
H16B H 0.6502 -0.0142 0.7044 0.092 Uiso 1 1 calc R
C17 C 0.7137(4) -0.1324(2) 0.7132(2) 0.1057(12) Uani 1 1 d .
H17A H 0.6363 -0.1810 0.7191 0.159 Uiso 1 1 calc R
H17B H 0.7871 -0.1391 0.7466 0.159 Uiso 1 1 calc R
H17C H 0.7098 -0.1482 0.6587 0.159 Uiso 1 1 calc R
C18 C 0.9726(3) 0.0620(2) 0.78010(16) 0.0759(9) Uani 1 1 d .
H18A H 0.9705 -0.0065 0.7591 0.091 Uiso 1 1 calc R
H18B H 1.0454 0.1157 0.7723 0.091 Uiso 1 1 calc R
C19 C 0.9955(4) 0.0771(3) 0.86943(19) 0.1191(14) Uani 1 1 d .
H19A H 1.0754 0.0731 0.8949 0.179 Uiso 1 1 calc R
H19B H 0.9259 0.0226 0.8782 0.179 Uiso 1 1 calc R
H19C H 0.9996 0.1452 0.8913 0.179 Uiso 1 1 calc R
C20 C 0.8488(2) 0.17480(19) 0.75989(14) 0.0520(6) Uani 1 1 d .
C21 C 0.7611(3) 0.2052(2) 0.78063(15) 0.0623(7) Uani 1 1 d .
H21 H 0.6815 0.1601 0.7821 0.075 Uiso 1 1 calc R
C22 C 0.8118(3) 0.3171(2) 0.79955(15) 0.0617(7) Uani 1 1 d .
H22 H 0.7715 0.3585 0.8152 0.074 Uiso 1 1 calc R
C23 C 0.9309(2) 0.35326(18) 0.79062(14) 0.0503(6) Uani 1 1 d .
C24 C 1.0259(2) 0.46239(18) 0.79469(14) 0.0519(7) Uani 1 1 d .
H24 H 1.1113 0.4612 0.8069 0.062 Uiso 1 1 calc R
C25 C 1.0323(3) 0.54401(19) 0.86216(17) 0.0601(7) Uani 1 1 d .
C26 C 0.9589(4) 0.6003(3) 0.8523(2) 0.1147(13) Uani 1 1 d .
H26 H 0.9041 0.5920 0.8020 0.138 Uiso 1 1 calc R
C27 C 0.9664(5) 0.6705(3) 0.9180(3) 0.1383(17) Uani 1 1 d .
H27 H 0.9152 0.7082 0.9126 0.166 Uiso 1 1 calc R
C28 C 1.0498(4) 0.6824(3) 0.9899(3) 0.1149(13) Uani 1 1 d .
H28 H 1.0576 0.7290 1.0349 0.138 Uiso 1 1 calc R
C29 C 1.1210(3) 0.6257(3) 0.99512(19) 0.0921(10) Uani 1 1 d .
H29 H 1.1792 0.6356 1.0446 0.111 Uiso 1 1 calc R
C30 C 0.9958(2) 0.48830(19) 0.71556(15) 0.0503(6) Uani 1 1 d .
C31 C 1.0698(3) 0.5546(2) 0.68105(17) 0.0668(8) Uani 1 1 d .
H31 H 1.1583 0.5951 0.7025 0.080 Uiso 1 1 calc R
C32 C 0.9879(3) 0.5510(2) 0.60639(17) 0.0633(7) Uani 1 1 d .
H32 H 1.0136 0.5889 0.5703 0.076 Uiso 1 1 calc R
C33 C 0.8663(2) 0.48320(18) 0.59669(15) 0.0483(6) Uani 1 1 d .
C34 C 0.7383(2) 0.45036(18) 0.53306(15) 0.0513(6) Uani 1 1 d .
C35 C 0.6559(3) 0.4969(2) 0.56776(17) 0.0682(8) Uani 1 1 d .
H35A H 0.5732 0.4755 0.5268 0.082 Uiso 1 1 calc R
H35B H 0.6396 0.4658 0.6113 0.082 Uiso 1 1 calc R
C36 C 0.7156(3) 0.6165(2) 0.5979(2) 0.1033(11) Uani 1 1 d .
H36A H 0.6585 0.6380 0.6184 0.155 Uiso 1 1 calc R
H36B H 0.7296 0.6484 0.5550 0.155 Uiso 1 1 calc R
H36C H 0.7966 0.6388 0.6395 0.155 Uiso 1 1 calc R
C37 C 0.7608(3) 0.4909(2) 0.46026(16) 0.0656(8) Uani 1 1 d .
H37A H 0.8043 0.5676 0.4765 0.079 Uiso 1 1 calc R
H37B H 0.8186 0.4650 0.4435 0.079 Uiso 1 1 calc R
C38 C 0.6399(3) 0.4596(3) 0.38852(18) 0.0914(10) Uani 1 1 d .
H38A H 0.6639 0.4886 0.3464 0.137 Uiso 1 1 calc R
H38B H 0.5827 0.4866 0.4036 0.137 Uiso 1 1 calc R
H38C H 0.5971 0.3838 0.3705 0.137 Uiso 1 1 calc R
C39 C 0.1069(3) 0.2616(2) 0.62523(18) 0.0685(8) Uani 1 1 d .
H39 H 0.0217 0.2527 0.6051 0.082 Uiso 1 1 calc R
C40 C 0.1621(4) 0.2322(2) 0.57324(18) 0.0765(9) Uani 1 1 d .
H40 H 0.1160 0.2045 0.5191 0.092 Uiso 1 1 calc R
C41 C 0.2864(4) 0.2445(2) 0.6029(2) 0.0796(9) Uani 1 1 d .
H41 H 0.3261 0.2232 0.5694 0.096 Uiso 1 1 calc R
C42 C 0.3535(3) 0.2887(2) 0.68321(18) 0.0709(8) Uani 1 1 d .
H42 H 0.4392 0.2990 0.7039 0.085 Uiso 1 1 calc R
C43 C 0.2920(3) 0.31754(18) 0.73268(15) 0.0514(6) Uani 1 1 d .
C44 C 0.3574(2) 0.37084(18) 0.82074(14) 0.0497(6) Uani 1 1 d .
H44 H 0.2887 0.3750 0.8405 0.060 Uiso 1 1 calc R
C45 C 0.4514(2) 0.48469(19) 0.83458(15) 0.0519(6) Uani 1 1 d .
C46 C 0.5512(3) 0.5313(2) 0.80785(17) 0.0706(8) Uani 1 1 d .
H46 H 0.5793 0.4968 0.7735 0.085 Uiso 1 1 calc R
C47 C 0.6046(3) 0.6419(2) 0.84168(17) 0.0712(8) Uani 1 1 d .
H47 H 0.6744 0.6926 0.8336 0.085 Uiso 1 1 calc R
C48 C 0.5367(2) 0.66085(19) 0.88774(16) 0.0554(7) Uani 1 1 d .
C49 C 0.5433(2) 0.76132(19) 0.93647(16) 0.0603(7) Uani 1 1 d .
C50 C 0.4262(3) 0.7829(2) 0.89343(18) 0.0801(9) Uani 1 1 d .
H50A H 0.3476 0.7235 0.8892 0.096 Uiso 1 1 calc R
H50B H 0.4288 0.8452 0.9261 0.096 Uiso 1 1 calc R
C51 C 0.4197(3) 0.7999(3) 0.8107(2) 0.1096(12) Uani 1 1 d .
H51A H 0.3447 0.8124 0.7884 0.164 Uiso 1 1 calc R
H51B H 0.4148 0.7380 0.7773 0.164 Uiso 1 1 calc R
H51C H 0.4957 0.8600 0.8143 0.164 Uiso 1 1 calc R
C52 C 0.6721(3) 0.8547(2) 0.94602(17) 0.0765(9) Uani 1 1 d .
H52A H 0.7427 0.8381 0.9729 0.092 Uiso 1 1 calc R
H52B H 0.6767 0.8597 0.8934 0.092 Uiso 1 1 calc R
C53 C 0.6928(4) 0.9626(2) 0.9916(2) 0.1137(13) Uani 1 1 d .
H53A H 0.7745 1.0148 0.9939 0.171 Uiso 1 1 calc R
H53B H 0.6919 0.9600 1.0447 0.171 Uiso 1 1 calc R
H53C H 0.6250 0.9813 0.9650 0.171 Uiso 1 1 calc R
C54 C 0.5374(3) 0.74598(19) 1.01741(17) 0.0581(7) Uani 1 1 d .
C55 C 0.4737(3) 0.7712(2) 1.06485(19) 0.0734(8) Uani 1 1 d .
H55 H 0.4200 0.8062 1.0532 0.088 Uiso 1 1 calc R
C56 C 0.5023(3) 0.7358(2) 1.13462(18) 0.0701(8) Uani 1 1 d .
H56 H 0.4708 0.7429 1.1766 0.084 Uiso 1 1 calc R
C57 C 0.5844(2) 0.68956(18) 1.12940(16) 0.0524(6) Uani 1 1 d .
N1 N 0.72518(19) 0.26758(16) 0.48798(12) 0.0531(6) Uani 1 1 d .
H1 H 0.801(2) 0.2906(19) 0.4821(14) 0.064 Uiso 1 1 d .
N2 N 0.7600(2) 0.08237(15) 0.59132(13) 0.0527(6) Uani 1 1 d .
H4 H 0.714(2) 0.1139(18) 0.6053(14) 0.063 Uiso 1 1 d .
N3 N 0.9522(2) 0.26601(16) 0.76657(11) 0.0508(5) Uani 1 1 d .
H6 H 1.022(2) 0.2731(18) 0.7495(14) 0.061 Uiso 1 1 d .
N4 N 0.8721(2) 0.44594(16) 0.66376(13) 0.0516(6) Uani 1 1 d .
H11 H 0.807(2) 0.3983(19) 0.6742(14) 0.062 Uiso 1 1 d .
N5 N 0.8381(2) 0.16936(17) 0.38860(14) 0.0692(6) Uani 1 1 d .
N6 N 1.1132(2) 0.55582(17) 0.93329(14) 0.0701(6) Uani 1 1 d .
N7 N 0.1685(2) 0.30251(15) 0.70380(13) 0.0566(6) Uani 1 1 d .
N8 N 0.4434(2) 0.56424(16) 0.88294(13) 0.0548(6) Uani 1 1 d .
H14 H 0.396(2) 0.5541(19) 0.9151(15) 0.066 Uiso 1 1 d .
N9 N 0.6064(2) 0.69765(16) 1.05869(13) 0.0551(6) Uani 1 1 d .
H15 H 0.643(2) 0.6626(19) 1.0385(15) 0.066 Uiso 1 1 d .
O1 O 1.2890(2) 0.46233(19) 0.98512(14) 0.0948(8) Uani 1 1 d .
H1W H 1.224(3) 0.484(3) 0.9647(19) 0.114 Uiso 1 1 d .
H2W H 1.303(3) 0.480(3) 1.037(2) 0.114 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'
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
C2 C1 N1 105.7(2) . .
C2 C1 C34 132.5(2) . .
N1 C1 C34 121.8(2) . .
C1 C2 C3 108.9(2) . .
C1 C2 H2 125.5 . .
C3 C2 H2 125.5 . .
C4 C3 C2 107.9(2) . .
C4 C3 H3 126.0 . .
C2 C3 H3 126.0 . .
C3 C4 N1 106.2(2) . .
C3 C4 C5 130.1(2) . .
N1 C4 C5 123.5(2) . .
C4 C5 C11 112.5(2) . .
C4 C5 C6 114.5(2) . .
C11 C5 C6 110.5(2) . .
C4 C5 H5 106.2 . .
C11 C5 H5 106.2 . .
C6 C5 H5 106.2 . .
N5 C6 C7 122.6(3) . .
N5 C6 C5 116.5(2) . .
C7 C6 C5 120.9(3) . .
C8 C7 C6 119.4(3) . .
C8 C7 H7 120.3 . .
C6 C7 H7 120.3 . .
C9 C8 C7 119.0(3) . .
C9 C8 H8 120.5 . .
C7 C8 H8 120.5 . .
C8 C9 C10 118.7(3) . .
C8 C9 H9 120.7 . .
C10 C9 H9 120.7 . .
N5 C10 C9 123.9(3) . .
N5 C10 H10 118.1 . .
C9 C10 H10 118.1 . .
C12 C11 N2 106.6(2) . .
C12 C11 C5 131.4(2) . .
N2 C11 C5 121.7(2) . .
C11 C12 C13 108.0(2) . .
C11 C12 H12 126.0 . .
C13 C12 H12 126.0 . .
C14 C13 C12 108.7(2) . .
C14 C13 H13 125.6 . .
C12 C13 H13 125.6 . .
C13 C14 N2 105.6(2) . .
C13 C14 C15 133.3(2) . .
N2 C14 C15 121.0(2) . .
C20 C15 C14 108.7(2) . .
C20 C15 C16 108.8(2) . .
C14 C15 C16 109.0(2) . .
C20 C15 C18 110.3(2) . .
C14 C15 C18 108.5(2) . .
C16 C15 C18 111.5(2) . .
C17 C16 C15 115.0(3) . .
C17 C16 H16A 108.5 . .
C15 C16 H16A 108.5 . .
C17 C16 H16B 108.5 . .
C15 C16 H16B 108.5 . .
H16A C16 H16B 107.5 . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C19 C18 C15 115.2(2) . .
C19 C18 H18A 108.5 . .
C15 C18 H18A 108.5 . .
C19 C18 H18B 108.5 . .
C15 C18 H18B 108.5 . .
H18A C18 H18B 107.5 . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C21 C20 N3 106.5(2) . .
C21 C20 C15 132.9(2) . .
N3 C20 C15 120.5(2) . .
C20 C21 C22 108.4(2) . .
C20 C21 H21 125.8 . .
C22 C21 H21 125.8 . .
C23 C22 C21 107.5(2) . .
C23 C22 H22 126.3 . .
C21 C22 H22 126.3 . .
C22 C23 N3 107.0(2) . .
C22 C23 C24 132.5(2) . .
N3 C23 C24 120.3(2) . .
C30 C24 C23 110.65(19) . .
C30 C24 C25 113.4(2) . .
C23 C24 C25 110.7(2) . .
C30 C24 H24 107.3 . .
C23 C24 H24 107.3 . .
C25 C24 H24 107.3 . .
N6 C25 C26 121.3(3) . .
N6 C25 C24 115.5(2) . .
C26 C25 C24 123.2(3) . .
C25 C26 C27 119.7(3) . .
C25 C26 H26 120.2 . .
C27 C26 H26 120.2 . .
C28 C27 C26 118.4(3) . .
C28 C27 H27 120.8 . .
C26 C27 H27 120.8 . .
C29 C28 C27 118.8(3) . .
C29 C28 H28 120.6 . .
C27 C28 H28 120.6 . .
N6 C29 C28 123.9(3) . .
N6 C29 H29 118.0 . .
C28 C29 H29 118.0 . .
C31 C30 N4 106.4(2) . .
C31 C30 C24 132.5(2) . .
N4 C30 C24 121.0(2) . .
C30 C31 C32 107.8(2) . .
C30 C31 H31 126.1 . .
C32 C31 H31 126.1 . .
C33 C32 C31 108.3(2) . .
C33 C32 H32 125.9 . .
C31 C32 H32 125.9 . .
C32 C33 N4 106.4(2) . .
C32 C33 C34 133.4(3) . .
N4 C33 C34 120.1(2) . .
C1 C34 C33 109.45(19) . .
C1 C34 C37 110.3(2) . .
C33 C34 C37 109.3(2) . .
C1 C34 C35 108.1(2) . .
C33 C34 C35 108.4(2) . .
C37 C34 C35 111.3(2) . .
C36 C35 C34 115.3(2) . .
C36 C35 H35A 108.5 . .
C34 C35 H35A 108.5 . .
C36 C35 H35B 108.5 . .
C34 C35 H35B 108.5 . .
H35A C35 H35B 107.5 . .
C35 C36 H36A 109.5 . .
C35 C36 H36B 109.5 . .
H36A C36 H36B 109.5 . .
C35 C36 H36C 109.5 . .
H36A C36 H36C 109.5 . .
H36B C36 H36C 109.5 . .
C38 C37 C34 115.8(2) . .
C38 C37 H37A 108.3 . .
C34 C37 H37A 108.3 . .
C38 C37 H37B 108.3 . .
C34 C37 H37B 108.3 . .
H37A C37 H37B 107.4 . .
C37 C38 H38A 109.5 . .
C37 C38 H38B 109.5 . .
H38A C38 H38B 109.5 . .
C37 C38 H38C 109.5 . .
H38A C38 H38C 109.5 . .
H38B C38 H38C 109.5 . .
N7 C39 C40 123.8(3) . .
N7 C39 H39 118.1 . .
C40 C39 H39 118.1 . .
C41 C40 C39 118.0(3) . .
C41 C40 H40 121.0 . .
C39 C40 H40 121.0 . .
C40 C41 C42 119.6(3) . .
C40 C41 H41 120.2 . .
C42 C41 H41 120.2 . .
C41 C42 C43 119.5(3) . .
C41 C42 H42 120.3 . .
C43 C42 H42 120.3 . .
N7 C43 C42 120.9(2) . .
N7 C43 C44 115.0(2) . .
C42 C43 C44 124.0(2) . .
C57 C44 C43 115.7(2) 2_667 .
C57 C44 C45 112.53(19) 2_667 .
C43 C44 C45 111.36(19) . .
C57 C44 H44 105.4 2_667 .
C43 C44 H44 105.4 . .
C45 C44 H44 105.4 . .
C46 C45 N8 106.6(2) . .
C46 C45 C44 133.5(2) . .
N8 C45 C44 120.0(2) . .
C45 C46 C47 107.8(3) . .
C45 C46 H46 126.1 . .
C47 C46 H46 126.1 . .
C48 C47 C46 108.2(2) . .
C48 C47 H47 125.9 . .
C46 C47 H47 125.9 . .
C47 C48 N8 106.5(2) . .
C47 C48 C49 133.5(2) . .
N8 C48 C49 120.0(2) . .
C54 C49 C48 109.0(2) . .
C54 C49 C50 109.2(2) . .
C48 C49 C50 109.0(2) . .
C54 C49 C52 109.7(2) . .
C48 C49 C52 109.0(2) . .
C50 C49 C52 110.8(2) . .
C51 C50 C49 114.9(3) . .
C51 C50 H50A 108.5 . .
C49 C50 H50A 108.5 . .
C51 C50 H50B 108.5 . .
C49 C50 H50B 108.5 . .
H50A C50 H50B 107.5 . .
C50 C51 H51A 109.5 . .
C50 C51 H51B 109.5 . .
H51A C51 H51B 109.5 . .
C50 C51 H51C 109.5 . .
H51A C51 H51C 109.5 . .
H51B C51 H51C 109.5 . .
C53 C52 C49 116.0(3) . .
C53 C52 H52A 108.3 . .
C49 C52 H52A 108.3 . .
C53 C52 H52B 108.3 . .
C49 C52 H52B 108.3 . .
H52A C52 H52B 107.4 . .
C52 C53 H53A 109.5 . .
C52 C53 H53B 109.5 . .
H53A C53 H53B 109.5 . .
C52 C53 H53C 109.5 . .
H53A C53 H53C 109.5 . .
H53B C53 H53C 109.5 . .
C55 C54 N9 105.5(3) . .
C55 C54 C49 133.4(3) . .
N9 C54 C49 121.1(2) . .
C54 C55 C56 108.9(2) . .
C54 C55 H55 125.6 . .
C56 C55 H55 125.6 . .
C57 C56 C55 107.6(3) . .
C57 C56 H56 126.2 . .
C55 C56 H56 126.2 . .
C56 C57 N9 106.6(2) . .
C56 C57 C44 134.6(3) . 2_667
N9 C57 C44 118.6(2) . 2_667
C4 N1 C1 111.2(2) . .
C4 N1 H1 124.1(16) . .
C1 N1 H1 124.3(16) . .
C11 N2 C14 111.1(2) . .
C11 N2 H4 126.0(16) . .
C14 N2 H4 122.9(16) . .
C23 N3 C20 110.6(2) . .
C23 N3 H6 120.2(15) . .
C20 N3 H6 128.3(15) . .
C33 N4 C30 111.1(2) . .
C33 N4 H11 127.2(16) . .
C30 N4 H11 121.6(15) . .
C6 N5 C10 116.5(2) . .
C25 N6 C29 117.9(3) . .
C43 N7 C39 118.2(2) . .
C45 N8 C48 110.9(2) . .
C45 N8 H14 124.3(16) . .
C48 N8 H14 123.5(17) . .
C57 N9 C54 111.3(2) . .
C57 N9 H15 122.3(17) . .
C54 N9 H15 124.7(17) . .
H1W O1 H2W 102(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.348(3) .
C1 N1 1.375(3) .
C1 C34 1.502(3) .
C2 C3 1.415(4) .
C2 H2 0.9300 .
C3 C4 1.352(3) .
C3 H3 0.9300 .
C4 N1 1.372(3) .
C4 C5 1.499(3) .
C5 C11 1.507(3) .
C5 C6 1.515(3) .
C5 H5 0.9800 .
C6 N5 1.335(3) .
C6 C7 1.375(3) .
C7 C8 1.373(4) .
C7 H7 0.9300 .
C8 C9 1.354(4) .
C8 H8 0.9300 .
C9 C10 1.368(4) .
C9 H9 0.9300 .
C10 N5 1.346(3) .
C10 H10 0.9300 .
C11 C12 1.362(3) .
C11 N2 1.367(3) .
C12 C13 1.409(3) .
C12 H12 0.9300 .
C13 C14 1.364(3) .
C13 H13 0.9300 .
C14 N2 1.383(3) .
C14 C15 1.512(3) .
C15 C20 1.511(3) .
C15 C16 1.547(3) .
C15 C18 1.547(3) .
C16 C17 1.529(4) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 C19 1.527(4) .
C18 H18A 0.9700 .
C18 H18B 0.9700 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C20 C21 1.364(3) .
C20 N3 1.372(3) .
C21 C22 1.414(3) .
C21 H21 0.9300 .
C22 C23 1.367(3) .
C22 H22 0.9300 .
C23 N3 1.370(3) .
C23 C24 1.508(3) .
C24 C30 1.497(3) .
C24 C25 1.517(3) .
C24 H24 0.9800 .
C25 N6 1.330(3) .
C25 C26 1.359(4) .
C26 C27 1.394(4) .
C26 H26 0.9300 .
C27 C28 1.353(5) .
C27 H27 0.9300 .
C28 C29 1.342(4) .
C28 H28 0.9300 .
C29 N6 1.339(3) .
C29 H29 0.9300 .
C30 C31 1.357(3) .
C30 N4 1.368(3) .
C31 C32 1.418(4) .
C31 H31 0.9300 .
C32 C33 1.351(3) .
C32 H32 0.9300 .
C33 N4 1.368(3) .
C33 C34 1.504(3) .
C34 C37 1.536(3) .
C34 C35 1.553(3) .
C35 C36 1.517(4) .
C35 H35A 0.9700 .
C35 H35B 0.9700 .
C36 H36A 0.9600 .
C36 H36B 0.9600 .
C36 H36C 0.9600 .
C37 C38 1.528(4) .
C37 H37A 0.9700 .
C37 H37B 0.9700 .
C38 H38A 0.9600 .
C38 H38B 0.9600 .
C38 H38C 0.9600 .
C39 N7 1.343(3) .
C39 C40 1.365(4) .
C39 H39 0.9300 .
C40 C41 1.360(4) .
C40 H40 0.9300 .
C41 C42 1.381(4) .
C41 H41 0.9300 .
C42 C43 1.387(3) .
C42 H42 0.9300 .
C43 N7 1.337(3) .
C43 C44 1.515(3) .
C44 C57 1.512(3) 2_667
C44 C45 1.516(3) .
C44 H44 0.9800 .
C45 C46 1.360(3) .
C45 N8 1.365(3) .
C46 C47 1.417(4) .
C46 H46 0.9300 .
C47 C48 1.352(3) .
C47 H47 0.9300 .
C48 N8 1.372(3) .
C48 C49 1.520(4) .
C49 C54 1.510(4) .
C49 C50 1.551(4) .
C49 C52 1.551(4) .
C50 C51 1.520(4) .
C50 H50A 0.9700 .
C50 H50B 0.9700 .
C51 H51A 0.9600 .
C51 H51B 0.9600 .
C51 H51C 0.9600 .
C52 C53 1.521(4) .
C52 H52A 0.9700 .
C52 H52B 0.9700 .
C53 H53A 0.9600 .
C53 H53B 0.9600 .
C53 H53C 0.9600 .
C54 C55 1.361(4) .
C54 N9 1.373(3) .
C55 C56 1.412(4) .
C55 H55 0.9300 .
C56 C57 1.359(3) .
C56 H56 0.9300 .
C57 N9 1.368(3) .
C57 C44 1.512(3) 2_667
N1 H1 0.87(2) .
N2 H4 0.87(2) .
N3 H6 0.93(2) .
N4 H11 0.90(2) .
N8 H14 0.89(2) .
N9 H15 0.86(2) .
O1 H1W 0.93(3) .
O1 H2W 0.88(3) .
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
O1 H1W N6 0.93(3) 1.93(3) 2.856(3) 169(3) .
N3 H6 N7 0.93(2) 2.03(2) 2.949(3) 172(2) 1_655
N8 H14 O1 0.89(2) 2.21(3) 3.035(3) 154(2) 1_455
N9 H15 O1 0.86(2) 2.21(2) 3.030(3) 159(2) 2_767
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_4
N1 C1 C2 C3 -1.2(3) . .
C34 C1 C2 C3 178.2(3) . .
C1 C2 C3 C4 0.8(3) . .
C2 C3 C4 N1 -0.1(3) . .
C2 C3 C4 C5 175.1(3) . .
C3 C4 C5 C11 -101.6(3) . .
N1 C4 C5 C11 72.9(3) . .
C3 C4 C5 C6 131.0(3) . .
N1 C4 C5 C6 -54.5(3) . .
C4 C5 C6 N5 56.1(3) . .
C11 C5 C6 N5 -72.4(3) . .
C4 C5 C6 C7 -125.4(3) . .
C11 C5 C6 C7 106.2(3) . .
N5 C6 C7 C8 0.1(4) . .
C5 C6 C7 C8 -178.4(3) . .
C6 C7 C8 C9 -0.3(5) . .
C7 C8 C9 C10 0.1(5) . .
C8 C9 C10 N5 0.4(5) . .
C4 C5 C11 C12 -157.1(3) . .
C6 C5 C11 C12 -27.6(4) . .
C4 C5 C11 N2 29.8(3) . .
C6 C5 C11 N2 159.2(2) . .
N2 C11 C12 C13 0.1(3) . .
C5 C11 C12 C13 -173.8(2) . .
C11 C12 C13 C14 -0.2(3) . .
C12 C13 C14 N2 0.1(3) . .
C12 C13 C14 C15 177.5(2) . .
C13 C14 C15 C20 140.7(3) . .
N2 C14 C15 C20 -42.3(3) . .
C13 C14 C15 C16 -100.9(3) . .
N2 C14 C15 C16 76.1(3) . .
C13 C14 C15 C18 20.8(4) . .
N2 C14 C15 C18 -162.2(2) . .
C20 C15 C16 C17 -177.9(2) . .
C14 C15 C16 C17 63.7(3) . .
C18 C15 C16 C17 -56.1(3) . .
C20 C15 C18 C19 60.3(3) . .
C14 C15 C18 C19 179.2(2) . .
C16 C15 C18 C19 -60.8(3) . .
C14 C15 C20 C21 110.6(3) . .
C16 C15 C20 C21 -8.0(4) . .
C18 C15 C20 C21 -130.6(3) . .
C14 C15 C20 N3 -66.9(3) . .
C16 C15 C20 N3 174.5(2) . .
C18 C15 C20 N3 51.9(3) . .
N3 C20 C21 C22 0.6(3) . .
C15 C20 C21 C22 -177.2(2) . .
C20 C21 C22 C23 -0.5(3) . .
C21 C22 C23 N3 0.3(3) . .
C21 C22 C23 C24 173.6(2) . .
C22 C23 C24 C30 -86.1(3) . .
N3 C23 C24 C30 86.5(3) . .
C22 C23 C24 C25 40.5(4) . .
N3 C23 C24 C25 -146.9(2) . .
C30 C24 C25 N6 -149.3(2) . .
C23 C24 C25 N6 85.6(3) . .
C30 C24 C25 C26 32.2(4) . .
C23 C24 C25 C26 -92.9(3) . .
N6 C25 C26 C27 -1.2(6) . .
C24 C25 C26 C27 177.2(4) . .
C25 C26 C27 C28 1.7(7) . .
C26 C27 C28 C29 -0.5(7) . .
C27 C28 C29 N6 -1.3(6) . .
C23 C24 C30 C31 -154.4(3) . .
C25 C24 C30 C31 80.5(3) . .
C23 C24 C30 N4 29.3(3) . .
C25 C24 C30 N4 -95.8(3) . .
N4 C30 C31 C32 -0.4(3) . .
C24 C30 C31 C32 -177.1(2) . .
C30 C31 C32 C33 0.0(3) . .
C31 C32 C33 N4 0.3(3) . .
C31 C32 C33 C34 176.6(2) . .
C2 C1 C34 C33 127.6(3) . .
N1 C1 C34 C33 -53.0(3) . .
C2 C1 C34 C37 -112.1(3) . .
N1 C1 C34 C37 67.3(3) . .
C2 C1 C34 C35 9.7(4) . .
N1 C1 C34 C35 -170.9(2) . .
C32 C33 C34 C1 132.5(3) . .
N4 C33 C34 C1 -51.6(3) . .
C32 C33 C34 C37 11.6(4) . .
N4 C33 C34 C37 -172.5(2) . .
C32 C33 C34 C35 -109.8(3) . .
N4 C33 C34 C35 66.1(3) . .
C1 C34 C35 C36 177.0(2) . .
C33 C34 C35 C36 58.5(3) . .
C37 C34 C35 C36 -61.8(3) . .
C1 C34 C37 C38 56.9(3) . .
C33 C34 C37 C38 177.3(2) . .
C35 C34 C37 C38 -63.0(3) . .
N7 C39 C40 C41 0.4(4) . .
C39 C40 C41 C42 -1.9(4) . .
C40 C41 C42 C43 1.5(4) . .
C41 C42 C43 N7 0.4(4) . .
C41 C42 C43 C44 -177.3(2) . .
N7 C43 C44 C57 123.5(2) . 2_667
C42 C43 C44 C57 -58.6(3) . 2_667
N7 C43 C44 C45 -106.3(2) . .
C42 C43 C44 C45 71.5(3) . .
C57 C44 C45 C46 79.5(3) 2_667 .
C43 C44 C45 C46 -52.3(4) . .
C57 C44 C45 N8 -100.6(3) 2_667 .
C43 C44 C45 N8 127.6(2) . .
N8 C45 C46 C47 0.3(3) . .
C44 C45 C46 C47 -179.8(2) . .
C45 C46 C47 C48 -0.3(3) . .
C46 C47 C48 N8 0.2(3) . .
C46 C47 C48 C49 -177.5(3) . .
C47 C48 C49 C54 -133.8(3) . .
N8 C48 C49 C54 48.7(3) . .
C47 C48 C49 C50 107.1(3) . .
N8 C48 C49 C50 -70.4(3) . .
C47 C48 C49 C52 -14.0(4) . .
N8 C48 C49 C52 168.4(2) . .
C54 C49 C50 C51 -180.0(2) . .
C48 C49 C50 C51 -61.0(3) . .
C52 C49 C50 C51 59.1(3) . .
C54 C49 C52 C53 -62.4(3) . .
C48 C49 C52 C53 178.3(2) . .
C50 C49 C52 C53 58.3(3) . .
C48 C49 C54 C55 -137.4(3) . .
C50 C49 C54 C55 -18.4(4) . .
C52 C49 C54 C55 103.2(3) . .
C48 C49 C54 N9 42.8(3) . .
C50 C49 C54 N9 161.8(2) . .
C52 C49 C54 N9 -76.6(3) . .
N9 C54 C55 C56 -1.2(3) . .
C49 C54 C55 C56 178.9(3) . .
C54 C55 C56 C57 0.4(3) . .
C55 C56 C57 N9 0.7(3) . .
C55 C56 C57 C44 -174.2(3) . 2_667
C3 C4 N1 C1 -0.7(3) . .
C5 C4 N1 C1 -176.3(2) . .
C2 C1 N1 C4 1.2(3) . .
C34 C1 N1 C4 -178.3(2) . .
C12 C11 N2 C14 0.0(3) . .
C5 C11 N2 C14 174.6(2) . .
C13 C14 N2 C11 -0.1(3) . .
C15 C14 N2 C11 -177.8(2) . .
C22 C23 N3 C20 0.1(3) . .
C24 C23 N3 C20 -174.2(2) . .
C21 C20 N3 C23 -0.4(3) . .
C15 C20 N3 C23 177.7(2) . .
C32 C33 N4 C30 -0.6(3) . .
C34 C33 N4 C30 -177.5(2) . .
C31 C30 N4 C33 0.6(3) . .
C24 C30 N4 C33 177.77(19) . .
C7 C6 N5 C10 0.3(4) . .
C5 C6 N5 C10 178.9(2) . .
C9 C10 N5 C6 -0.6(4) . .
C26 C25 N6 C29 -0.5(4) . .
C24 C25 N6 C29 -179.0(3) . .
C28 C29 N6 C25 1.8(5) . .
C42 C43 N7 C39 -1.9(3) . .
C44 C43 N7 C39 176.0(2) . .
C40 C39 N7 C43 1.5(4) . .
C46 C45 N8 C48 -0.2(3) . .
C44 C45 N8 C48 179.9(2) . .
C47 C48 N8 C45 0.0(3) . .
C49 C48 N8 C45 178.1(2) . .
C56 C57 N9 C54 -1.5(3) . .
C44 C57 N9 C54 174.3(2) 2_667 .
C55 C54 N9 C57 1.7(3) . .
C49 C54 N9 C57 -178.4(2) . .
