#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/69/2016924.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2016924
loop_
_publ_author_name
'Lipstman, Sophia'
'Goldberg, Israel'
_publ_section_title
;
 Hydrogen-bonded assemblies of
 5,10,15,20-tetrakis(4-hydroxyphenyl)porphyrin with dimethylformamide,
 dimethylacetamide and water
;
_journal_coeditor_code           GD3260
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o3
_journal_page_last               o7
_journal_paper_doi               10.1107/S0108270108040018
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C44 H30 N4 O4 , 4C3 H7 N O , H2 O'
_chemical_formula_moiety         'C44 H30 N4 O4 , 4C3 H7 N O , H2 O'
_chemical_formula_sum            'C56 H60 N8 O9'
_chemical_formula_weight         989.12
_chemical_name_systematic
;
5,10,15,20-tetrakis(4-hydroxyphenyl)porphyrin
N,N'-dimethylformamide tetrasolvate monohydrate
;
_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           SHELXL97
_cell_angle_alpha                102.8305(6)
_cell_angle_beta                 90.2339(6)
_cell_angle_gamma                104.3547(11)
_cell_formula_units_Z            2
_cell_length_a                   12.8346(2)
_cell_length_b                   13.6669(2)
_cell_length_c                   15.3200(3)
_cell_measurement_reflns_used    8903
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      28.18
_cell_measurement_theta_min      1.97
_cell_volume                     2533.39(7)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al.,
2006)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 12.8
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       '1 deg. φ and 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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            26977
_diffrn_reflns_theta_full        28.18
_diffrn_reflns_theta_max         28.18
_diffrn_reflns_theta_min         1.97
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.440
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     670
_refine_ls_number_reflns         12018
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0528
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0787P)²+1.1683P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1355
_refine_ls_wR_factor_ref         0.1526
_reflns_number_gt                8881
_reflns_number_total             12018
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gd3260.cif
_cod_data_source_block           II
_cod_database_code               2016924
_cod_database_fobs_code          2016924
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.56080(12) 0.19555(12) 0.64950(10) 0.0166(3) Uani d . 1 . .
C C2 0.53238(13) 0.26145(13) 0.72686(11) 0.0185(3) Uani d . 1 . .
H H2 0.5524 0.2647 0.7874 0.022 Uiso calc R 1 . .
C C3 0.47164(13) 0.31892(13) 0.69897(11) 0.0195(3) Uani d . 1 . .
H H3 0.4417 0.3687 0.7367 0.023 Uiso calc R 1 . .
C C4 0.46088(12) 0.29134(12) 0.60344(11) 0.0172(3) Uani d . 1 . .
C C5 0.40455(12) 0.33196(12) 0.54693(11) 0.0168(3) Uani d . 1 . .
C C6 0.41308(12) 0.31675(12) 0.45343(11) 0.0169(3) Uani d . 1 . .
C C7 0.35467(13) 0.35920(13) 0.39555(11) 0.0196(3) Uani d . 1 . .
H H7 0.3004 0.3949 0.4124 0.023 Uiso calc R 1 . .
C C8 0.39269(13) 0.33792(13) 0.31332(11) 0.0201(3) Uani d . 1 . .
H H8 0.3721 0.3574 0.2613 0.024 Uiso calc R 1 . .
C C9 0.47136(12) 0.27930(12) 0.32015(11) 0.0168(3) Uani d . 1 . .
C C10 0.52915(12) 0.24391(12) 0.24701(10) 0.0171(3) Uani d . 1 . .
C C11 0.59708(12) 0.17820(12) 0.24766(11) 0.0178(3) Uani d . 1 . .
C C12 0.65545(13) 0.13922(13) 0.17448(11) 0.0195(3) Uani d . 1 . .
H H12 0.6582 0.1565 0.1177 0.023 Uiso calc R 1 . .
C C13 0.70640(13) 0.07296(13) 0.20033(11) 0.0193(3) Uani d . 1 . .
H H13 0.7504 0.0356 0.1644 0.023 Uiso calc R 1 . .
C C14 0.68251(12) 0.06908(12) 0.29068(11) 0.0171(3) Uani d . 1 . .
C C15 0.71637(12) 0.00875(12) 0.34241(10) 0.0166(3) Uani d . 1 . .
C C16 0.69680(12) 0.01359(12) 0.43354(11) 0.0164(3) Uani d . 1 . .
C C17 0.72678(13) -0.05453(12) 0.48456(11) 0.0184(3) Uani d . 1 . .
H H17 0.7589 -0.1100 0.4624 0.022 Uiso calc R 1 . .
C C18 0.70002(13) -0.02331(12) 0.56960(11) 0.0189(3) Uani d . 1 . .
H H18 0.7094 -0.0526 0.6189 0.023 Uiso calc R 1 . .
C C19 0.65399(12) 0.06410(12) 0.57066(10) 0.0164(3) Uani d . 1 . .
C C20 0.61980(12) 0.12166(12) 0.64875(10) 0.0164(3) Uani d . 1 . .
N N21 0.51817(10) 0.21809(10) 0.57605(9) 0.0162(3) Uani d . 1 . .
H H21 0.5263 0.1899 0.5198 0.019 Uiso calc PR 0.50 . .
N N22 0.48155(10) 0.26586(10) 0.40497(9) 0.0165(3) Uani d . 1 . .
H H22 0.5231 0.2318 0.4245 0.020 Uiso calc PR 0.50 . .
N N23 0.61723(10) 0.13538(10) 0.31727(9) 0.0168(3) Uani d . 1 . .
H H23 0.5922 0.1484 0.3708 0.020 Uiso calc PR 0.50 . .
N N24 0.65080(10) 0.08352(10) 0.48694(9) 0.0163(3) Uani d . 1 . .
H H24 0.6246 0.1311 0.4709 0.020 Uiso calc PR 0.50 . .
C C25 0.33294(12) 0.39654(12) 0.59124(10) 0.0171(3) Uani d . 1 . .
C C26 0.25298(13) 0.35684(13) 0.64513(11) 0.0191(3) Uani d . 1 . .
H H26 0.2450 0.2886 0.6534 0.023 Uiso calc R 1 . .
C C27 0.18497(13) 0.41550(13) 0.68678(11) 0.0205(3) Uani d . 1 . .
H H27 0.1308 0.3869 0.7227 0.025 Uiso calc R 1 . .
C C28 0.19615(13) 0.51572(13) 0.67598(11) 0.0192(3) Uani d . 1 . .
C C29 0.27533(13) 0.55676(13) 0.62234(11) 0.0195(3) Uani d . 1 . .
H H29 0.2831 0.6250 0.6142 0.023 Uiso calc R 1 . .
C C30 0.34274(12) 0.49744(12) 0.58094(11) 0.0182(3) Uani d . 1 . .
H H30 0.3966 0.5261 0.5449 0.022 Uiso calc R 1 . .
O O31 0.13042(10) 0.57136(10) 0.72111(9) 0.0275(3) Uani d . 1 . .
H H31 0.1306 0.6221 0.6985 0.041 Uiso calc R 1 . .
C C32 0.52238(13) 0.28101(13) 0.16308(11) 0.0183(3) Uani d . 1 . .
C C33 0.57589(14) 0.38248(13) 0.16094(12) 0.0237(4) Uani d . 1 . .
H H33 0.6120 0.4285 0.2143 0.028 Uiso calc R 1 . .
C C34 0.57758(14) 0.41772(14) 0.08266(12) 0.0261(4) Uani d . 1 . .
H H34 0.6157 0.4868 0.0824 0.031 Uiso calc R 1 . .
C C35 0.52334(15) 0.35162(14) 0.00458(11) 0.0249(4) Uani d . 1 . .
C C36 0.46762(15) 0.25109(14) 0.00631(12) 0.0270(4) Uani d . 1 . .
H H36 0.4295 0.2059 -0.0466 0.032 Uiso calc R 1 . .
C C37 0.46720(14) 0.21633(14) 0.08461(11) 0.0242(4) Uani d . 1 . .
H H37 0.4287 0.1474 0.0848 0.029 Uiso calc R 1 . .
O O38 0.52169(13) 0.38207(11) -0.07420(9) 0.0345(3) Uani d . 1 . .
H H38 0.5686 0.4382 -0.0704 0.052 Uiso calc R 1 . .
C C39 0.78044(12) -0.06297(12) 0.29604(10) 0.0171(3) Uani d . 1 . .
C C40 0.73460(13) -0.14665(13) 0.22490(11) 0.0200(3) Uani d . 1 . .
H H40 0.6610 -0.1586 0.2062 0.024 Uiso calc R 1 . .
C C41 0.79400(13) -0.21273(13) 0.18089(11) 0.0212(3) Uani d . 1 . .
H H41 0.7608 -0.2699 0.1334 0.025 Uiso calc R 1 . .
C C42 0.90236(14) -0.19482(13) 0.20673(11) 0.0211(3) Uani d . 1 . .
C C43 0.94989(13) -0.11096(13) 0.27621(12) 0.0231(4) Uani d . 1 . .
H H43 1.0242 -0.0978 0.2935 0.028 Uiso calc R 1 . .
C C44 0.88926(13) -0.04628(13) 0.32064(11) 0.0213(3) Uani d . 1 . .
H H44 0.9225 0.0103 0.3686 0.026 Uiso calc R 1 . .
O O45 0.96531(10) -0.25729(10) 0.16743(9) 0.0290(3) Uani d . 1 . .
H H45 0.9280 -0.3065 0.1279 0.044 Uiso calc R 1 . .
C C46 0.64909(12) 0.10367(12) 0.73713(10) 0.0169(3) Uani d . 1 . .
C C47 0.75628(13) 0.11671(13) 0.76476(11) 0.0192(3) Uani d . 1 . .
H H47 0.8114 0.1389 0.7270 0.023 Uiso calc R 1 . .
C C48 0.78475(13) 0.09814(13) 0.84601(11) 0.0217(3) Uani d . 1 . .
H H48 0.8584 0.1076 0.8633 0.026 Uiso calc R 1 . .
C C49 0.70460(14) 0.06552(13) 0.90199(11) 0.0201(3) Uani d . 1 . .
C C50 0.59727(14) 0.05538(13) 0.87670(11) 0.0212(3) Uani d . 1 . .
H H50 0.5424 0.0356 0.9155 0.025 Uiso calc R 1 . .
C C51 0.57033(13) 0.07397(12) 0.79559(11) 0.0192(3) Uani d . 1 . .
H H51 0.4968 0.0664 0.7792 0.023 Uiso calc R 1 . .
O O52 0.72536(10) 0.04259(10) 0.98108(8) 0.0280(3) Uani d . 1 . .
H H52 0.7922 0.0589 0.9930 0.042 Uiso calc R 1 . .
O O53 0.09389(10) 0.72612(10) 0.65338(9) 0.0316(3) Uani d . 1 . .
C C54 0.11087(15) 0.75753(13) 0.58384(12) 0.0263(4) Uani d . 1 . .
H H54 0.1819 0.7676 0.5638 0.032 Uiso calc R 1 . .
N N55 0.03633(12) 0.77824(12) 0.53496(11) 0.0289(3) Uani d . 1 . .
C C56 0.06214(18) 0.81358(18) 0.45339(14) 0.0406(5) Uani d . 1 . .
H H56A 0.1379 0.8170 0.4423 0.061 Uiso calc R 1 . .
H H56B 0.0497 0.8827 0.4598 0.061 Uiso calc R 1 . .
H H56C 0.0162 0.7650 0.4029 0.061 Uiso calc R 1 . .
C C57 -0.07409(17) 0.76465(19) 0.56046(16) 0.0414(5) Uani d . 1 . .
H H57A -0.0798 0.7465 0.6190 0.062 Uiso calc R 1 . .
H H57B -0.1215 0.7089 0.5155 0.062 Uiso calc R 1 . .
H H57C -0.0956 0.8294 0.5642 0.062 Uiso calc R 1 . .
O O58 0.86664(12) -0.42799(11) 0.04797(10) 0.0414(4) Uani d . 1 . .
C C59 0.88094(19) -0.50648(16) 0.06877(15) 0.0395(5) Uani d . 1 . .
H H59 0.9058 -0.4991 0.1290 0.047 Uiso calc R 1 . .
N N60 0.86483(16) -0.59908(13) 0.01506(13) 0.0421(4) Uani d . 1 . .
C C61 0.8830(3) -0.6867(2) 0.0472(2) 0.0787(11) Uani d . 1 . .
H H61A 0.9132 -0.6626 0.1093 0.118 Uiso calc R 1 . .
H H61B 0.9335 -0.7173 0.0094 0.118 Uiso calc R 1 . .
H H61C 0.8144 -0.7390 0.0443 0.118 Uiso calc R 1 . .
C C62 0.8298(2) -0.6178(2) -0.07958(17) 0.0527(6) Uani d . 1 . .
H H62A 0.7528 -0.6532 -0.0884 0.079 Uiso calc R 1 . .
H H62B 0.8709 -0.6614 -0.1164 0.079 Uiso calc R 1 . .
H H62C 0.8421 -0.5514 -0.0973 0.079 Uiso calc R 1 . .
O O63 0.93357(12) 0.08821(13) 1.02441(11) 0.0448(4) Uani d . 1 . .
C C64 0.98721(16) 0.09577(16) 1.09406(14) 0.0344(4) Uani d . 1 . .
H H64 0.9507 0.0681 1.1405 0.041 Uiso calc R 1 . .
N N65 1.09128(13) 0.13954(13) 1.10831(11) 0.0317(4) Uani d . 1 . .
C C66 1.14945(18) 0.14594(18) 1.19120(15) 0.0419(5) Uani d . 1 . .
H H66A 1.1003 0.1114 1.2303 0.063 Uiso calc R 1 . .
H H66B 1.1793 0.2190 1.2213 0.063 Uiso calc R 1 . .
H H66C 1.2082 0.1117 1.1782 0.063 Uiso calc R 1 . .
C C67 1.1531(2) 0.1799(2) 1.03880(18) 0.0504(6) Uani d . 1 . .
H H67A 1.1051 0.1692 0.9857 0.076 Uiso calc R 1 . .
H H67B 1.2095 0.1434 1.0228 0.076 Uiso calc R 1 . .
H H67C 1.1862 0.2542 1.0611 0.076 Uiso calc R 1 . .
O O68 0.81306(16) 0.58539(16) -0.20961(13) 0.0637(5) Uani d . 1 . .
C C69 0.86683(17) 0.57297(18) -0.27516(15) 0.0384(5) Uani d . 1 . .
H H69 0.9292 0.6268 -0.2773 0.046 Uiso calc R 1 . .
N N70 0.84512(14) 0.49075(14) -0.34320(14) 0.0433(5) Uani d . 1 . .
C C71 0.91475(19) 0.48164(19) -0.41760(16) 0.0456(5) Uani d . 1 . .
H H71A 0.9706 0.5468 -0.4113 0.068 Uiso calc R 1 . .
H H71B 0.8719 0.4671 -0.4742 0.068 Uiso calc R 1 . .
H H71C 0.9487 0.4249 -0.4175 0.068 Uiso calc R 1 . .
C C72 0.7531(3) 0.4046(3) -0.3454(3) 0.1008(14) Uani d . 1 . .
H H72A 0.7044 0.4252 -0.2998 0.151 Uiso calc R 1 . .
H H72B 0.7772 0.3460 -0.3331 0.151 Uiso calc R 1 . .
H H72C 0.7150 0.3839 -0.4048 0.151 Uiso calc R 1 . .
O O73 0.68215(13) 0.55635(13) -0.06864(12) 0.0502(4) Uani d . 1 . .
H H73A 0.7387 0.5612 -0.0328 0.075 Uiso d R 1 . .
H H73B 0.7239 0.5657 -0.1140 0.075 Uiso d R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N21 C1 C20 . . 126.78(14) ?
N21 C1 C2 . . 106.60(13) ?
C20 C1 C2 . . 126.62(14) ?
C3 C2 C1 . . 108.33(14) ?
C3 C2 H2 . . 125.8 ?
C1 C2 H2 . . 125.8 ?
C2 C3 C4 . . 108.17(14) ?
C2 C3 H3 . . 125.9 ?
C4 C3 H3 . . 125.9 ?
N21 C4 C5 . . 126.06(14) ?
N21 C4 C3 . . 106.81(13) ?
C5 C4 C3 . . 127.11(14) ?
C6 C5 C4 . . 124.51(14) ?
C6 C5 C25 . . 119.05(14) ?
C4 C5 C25 . . 116.43(14) ?
N22 C6 C5 . . 125.28(14) ?
N22 C6 C7 . . 110.47(14) ?
C5 C6 C7 . . 124.14(14) ?
C8 C7 C6 . . 106.58(14) ?
C8 C7 H7 . . 126.7 ?
C6 C7 H7 . . 126.7 ?
C7 C8 C9 . . 106.33(14) ?
C7 C8 H8 . . 126.8 ?
C9 C8 H8 . . 126.8 ?
N22 C9 C10 . . 126.09(14) ?
N22 C9 C8 . . 111.25(13) ?
C10 C9 C8 . . 122.66(14) ?
C11 C10 C9 . . 124.67(14) ?
C11 C10 C32 . . 116.30(13) ?
C9 C10 C32 . . 118.99(13) ?
N23 C11 C10 . . 126.85(14) ?
N23 C11 C12 . . 106.81(13) ?
C10 C11 C12 . . 126.30(15) ?
C13 C12 C11 . . 108.14(14) ?
C13 C12 H12 . . 125.9 ?
C11 C12 H12 . . 125.9 ?
C12 C13 C14 . . 108.43(14) ?
C12 C13 H13 . . 125.8 ?
C14 C13 H13 . . 125.8 ?
N23 C14 C15 . . 126.15(14) ?
N23 C14 C13 . . 106.57(13) ?
C15 C14 C13 . . 127.27(14) ?
C14 C15 C16 . . 124.79(14) ?
C14 C15 C39 . . 115.97(14) ?
C16 C15 C39 . . 119.21(14) ?
N24 C16 C15 . . 125.51(14) ?
N24 C16 C17 . . 110.61(13) ?
C15 C16 C17 . . 123.85(14) ?
C18 C17 C16 . . 106.61(14) ?
C18 C17 H17 . . 126.7 ?
C16 C17 H17 . . 126.7 ?
C17 C18 C19 . . 106.36(14) ?
C17 C18 H18 . . 126.8 ?
C19 C18 H18 . . 126.8 ?
N24 C19 C20 . . 125.33(14) ?
N24 C19 C18 . . 110.81(13) ?
C20 C19 C18 . . 123.85(14) ?
C1 C20 C19 . . 124.78(14) ?
C1 C20 C46 . . 117.21(13) ?
C19 C20 C46 . . 118.01(13) ?
C1 N21 C4 . . 110.02(13) ?
C1 N21 H21 . . 125.0 ?
C4 N21 H21 . . 125.0 ?
C9 N22 C6 . . 105.29(13) ?
C9 N22 H22 . . 127.4 ?
C6 N22 H22 . . 127.4 ?
C11 N23 C14 . . 110.02(13) ?
C11 N23 H23 . . 125.0 ?
C14 N23 H23 . . 125.0 ?
C16 N24 C19 . . 105.57(13) ?
C16 N24 H24 . . 127.2 ?
C19 N24 H24 . . 127.2 ?
C30 C25 C26 . . 117.82(14) ?
C30 C25 C5 . . 121.95(14) ?
C26 C25 C5 . . 120.23(14) ?
C27 C26 C25 . . 121.22(15) ?
C27 C26 H26 . . 119.4 ?
C25 C26 H26 . . 119.4 ?
C28 C27 C26 . . 120.12(15) ?
C28 C27 H27 . . 119.9 ?
C26 C27 H27 . . 119.9 ?
O31 C28 C27 . . 117.79(14) ?
O31 C28 C29 . . 122.62(15) ?
C27 C28 C29 . . 119.56(14) ?
C30 C29 C28 . . 119.84(15) ?
C30 C29 H29 . . 120.1 ?
C28 C29 H29 . . 120.1 ?
C29 C30 C25 . . 121.43(15) ?
C29 C30 H30 . . 119.3 ?
C25 C30 H30 . . 119.3 ?
C28 O31 H31 . . 109.5 ?
C37 C32 C33 . . 118.01(15) ?
C37 C32 C10 . . 122.21(15) ?
C33 C32 C10 . . 119.74(15) ?
C34 C33 C32 . . 121.46(16) ?
C34 C33 H33 . . 119.3 ?
C32 C33 H33 . . 119.3 ?
C33 C34 C35 . . 119.75(17) ?
C33 C34 H34 . . 120.1 ?
C35 C34 H34 . . 120.1 ?
O38 C35 C36 . . 118.26(17) ?
O38 C35 C34 . . 122.37(17) ?
C36 C35 C34 . . 119.37(16) ?
C37 C36 C35 . . 120.46(16) ?
C37 C36 H36 . . 119.8 ?
C35 C36 H36 . . 119.8 ?
C36 C37 C32 . . 120.93(16) ?
C36 C37 H37 . . 119.5 ?
C32 C37 H37 . . 119.5 ?
C35 O38 H38 . . 109.5 ?
C44 C39 C40 . . 117.74(14) ?
C44 C39 C15 . . 120.90(14) ?
C40 C39 C15 . . 121.33(14) ?
C41 C40 C39 . . 121.60(15) ?
C41 C40 H40 . . 119.2 ?
C39 C40 H40 . . 119.2 ?
C40 C41 C42 . . 119.69(15) ?
C40 C41 H41 . . 120.2 ?
C42 C41 H41 . . 120.2 ?
O45 C42 C43 . . 117.49(15) ?
O45 C42 C41 . . 122.93(15) ?
C43 C42 C41 . . 119.57(14) ?
C42 C43 C44 . . 120.23(15) ?
C42 C43 H43 . . 119.9 ?
C44 C43 H43 . . 119.9 ?
C43 C44 C39 . . 121.16(16) ?
C43 C44 H44 . . 119.4 ?
C39 C44 H44 . . 119.4 ?
C42 O45 H45 . . 109.5 ?
C47 C46 C51 . . 117.55(14) ?
C47 C46 C20 . . 121.13(14) ?
C51 C46 C20 . . 121.31(14) ?
C48 C47 C46 . . 121.83(14) ?
C48 C47 H47 . . 119.1 ?
C46 C47 H47 . . 119.1 ?
C47 C48 C49 . . 119.59(15) ?
C47 C48 H48 . . 120.2 ?
C49 C48 H48 . . 120.2 ?
O52 C49 C48 . . 123.26(15) ?
O52 C49 C50 . . 117.46(14) ?
C48 C49 C50 . . 119.27(15) ?
C51 C50 C49 . . 120.36(15) ?
C51 C50 H50 . . 119.8 ?
C49 C50 H50 . . 119.8 ?
C50 C51 C46 . . 121.32(15) ?
C50 C51 H51 . . 119.3 ?
C46 C51 H51 . . 119.3 ?
C49 O52 H52 . . 109.5 ?
O53 C54 N55 . . 124.46(17) ?
O53 C54 H54 . . 117.8 ?
N55 C54 H54 . . 117.8 ?
C54 N55 C56 . . 121.25(17) ?
C54 N55 C57 . . 121.42(16) ?
C56 N55 C57 . . 117.32(17) ?
N55 C56 H56A . . 109.5 ?
N55 C56 H56B . . 109.5 ?
H56A C56 H56B . . 109.5 ?
N55 C56 H56C . . 109.5 ?
H56A C56 H56C . . 109.5 ?
H56B C56 H56C . . 109.5 ?
N55 C57 H57A . . 109.5 ?
N55 C57 H57B . . 109.5 ?
H57A C57 H57B . . 109.5 ?
N55 C57 H57C . . 109.5 ?
H57A C57 H57C . . 109.5 ?
H57B C57 H57C . . 109.5 ?
O58 C59 N60 . . 125.9(2) ?
O58 C59 H59 . . 117.1 ?
N60 C59 H59 . . 117.1 ?
C59 N60 C61 . . 121.3(2) ?
C59 N60 C62 . . 121.3(2) ?
C61 N60 C62 . . 117.5(2) ?
N60 C61 H61A . . 109.5 ?
N60 C61 H61B . . 109.5 ?
H61A C61 H61B . . 109.5 ?
N60 C61 H61C . . 109.5 ?
H61A C61 H61C . . 109.5 ?
H61B C61 H61C . . 109.5 ?
N60 C62 H62A . . 109.5 ?
N60 C62 H62B . . 109.5 ?
H62A C62 H62B . . 109.5 ?
N60 C62 H62C . . 109.5 ?
H62A C62 H62C . . 109.5 ?
H62B C62 H62C . . 109.5 ?
O63 C64 N65 . . 124.6(2) ?
O63 C64 H64 . . 117.7 ?
N65 C64 H64 . . 117.7 ?
C64 N65 C66 . . 121.95(18) ?
C64 N65 C67 . . 120.64(19) ?
C66 N65 C67 . . 117.37(18) ?
N65 C66 H66A . . 109.5 ?
N65 C66 H66B . . 109.5 ?
H66A C66 H66B . . 109.5 ?
N65 C66 H66C . . 109.5 ?
H66A C66 H66C . . 109.5 ?
H66B C66 H66C . . 109.5 ?
N65 C67 H67A . . 109.5 ?
N65 C67 H67B . . 109.5 ?
H67A C67 H67B . . 109.5 ?
N65 C67 H67C . . 109.5 ?
H67A C67 H67C . . 109.5 ?
H67B C67 H67C . . 109.5 ?
O68 C69 N70 . . 125.4(2) ?
O68 C69 H69 . . 117.3 ?
N70 C69 H69 . . 117.3 ?
C69 N70 C72 . . 121.3(2) ?
C69 N70 C71 . . 121.64(18) ?
C72 N70 C71 . . 117.0(2) ?
N70 C71 H71A . . 109.5 ?
N70 C71 H71B . . 109.5 ?
H71A C71 H71B . . 109.5 ?
N70 C71 H71C . . 109.5 ?
H71A C71 H71C . . 109.5 ?
H71B C71 H71C . . 109.5 ?
N70 C72 H72A . . 109.5 ?
N70 C72 H72B . . 109.5 ?
H72A C72 H72B . . 109.5 ?
N70 C72 H72C . . 109.5 ?
H72A C72 H72C . . 109.5 ?
H72B C72 H72C . . 109.5 ?
H73A O73 H73B . . 91.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N21 . 1.376(2) ?
C1 C20 . 1.403(2) ?
C1 C2 . 1.429(2) ?
C2 C3 . 1.363(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.425(2) ?
C3 H3 . 0.9500 ?
C4 N21 . 1.3785(19) ?
C4 C5 . 1.410(2) ?
C5 C6 . 1.410(2) ?
C5 C25 . 1.492(2) ?
C6 N22 . 1.3735(19) ?
C6 C7 . 1.457(2) ?
C7 C8 . 1.350(2) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.453(2) ?
C8 H8 . 0.9500 ?
C9 N22 . 1.362(2) ?
C9 C10 . 1.408(2) ?
C10 C11 . 1.400(2) ?
C10 C32 . 1.493(2) ?
C11 N23 . 1.377(2) ?
C11 C12 . 1.429(2) ?
C12 C13 . 1.362(2) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.429(2) ?
C13 H13 . 0.9500 ?
C14 N23 . 1.3800(19) ?
C14 C15 . 1.401(2) ?
C15 C16 . 1.410(2) ?
C15 C39 . 1.496(2) ?
C16 N24 . 1.3666(19) ?
C16 C17 . 1.457(2) ?
C17 C18 . 1.352(2) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.455(2) ?
C18 H18 . 0.9500 ?
C19 N24 . 1.369(2) ?
C19 C20 . 1.414(2) ?
C20 C46 . 1.492(2) ?
N21 H21 . 0.8800 ?
N22 H22 . 0.8800 ?
N23 H23 . 0.8800 ?
N24 H24 . 0.8800 ?
C25 C30 . 1.398(2) ?
C25 C26 . 1.400(2) ?
C26 C27 . 1.391(2) ?
C26 H26 . 0.9500 ?
C27 C28 . 1.388(2) ?
C27 H27 . 0.9500 ?
C28 O31 . 1.3629(19) ?
C28 C29 . 1.397(2) ?
C29 C30 . 1.390(2) ?
C29 H29 . 0.9500 ?
C30 H30 . 0.9500 ?
O31 H31 . 0.8400 ?
C32 C37 . 1.392(2) ?
C32 C33 . 1.394(2) ?
C33 C34 . 1.386(2) ?
C33 H33 . 0.9500 ?
C34 C35 . 1.390(3) ?
C34 H34 . 0.9500 ?
C35 O38 . 1.363(2) ?
C35 C36 . 1.389(3) ?
C36 C37 . 1.384(2) ?
C36 H36 . 0.9500 ?
C37 H37 . 0.9500 ?
O38 H38 . 0.8400 ?
C39 C44 . 1.394(2) ?
C39 C40 . 1.396(2) ?
C40 C41 . 1.388(2) ?
C40 H40 . 0.9500 ?
C41 C42 . 1.391(2) ?
C41 H41 . 0.9500 ?
C42 O45 . 1.3645(19) ?
C42 C43 . 1.387(2) ?
C43 C44 . 1.389(2) ?
C43 H43 . 0.9500 ?
C44 H44 . 0.9500 ?
O45 H45 . 0.8400 ?
C46 C47 . 1.394(2) ?
C46 C51 . 1.398(2) ?
C47 C48 . 1.389(2) ?
C47 H47 . 0.9500 ?
C48 C49 . 1.394(2) ?
C48 H48 . 0.9500 ?
C49 O52 . 1.358(2) ?
C49 C50 . 1.394(2) ?
C50 C51 . 1.382(2) ?
C50 H50 . 0.9500 ?
C51 H51 . 0.9500 ?
O52 H52 . 0.8400 ?
O53 C54 . 1.235(2) ?
C54 N55 . 1.334(2) ?
C54 H54 . 0.9500 ?
N55 C56 . 1.448(3) ?
N55 C57 . 1.450(3) ?
C56 H56A . 0.9800 ?
C56 H56B . 0.9800 ?
C56 H56C . 0.9800 ?
C57 H57A . 0.9800 ?
C57 H57B . 0.9800 ?
C57 H57C . 0.9800 ?
O58 C59 . 1.239(3) ?
C59 N60 . 1.314(3) ?
C59 H59 . 0.9500 ?
N60 C61 . 1.459(3) ?
N60 C62 . 1.464(3) ?
C61 H61A . 0.9800 ?
C61 H61B . 0.9800 ?
C61 H61C . 0.9800 ?
C62 H62A . 0.9800 ?
C62 H62B . 0.9800 ?
C62 H62C . 0.9800 ?
O63 C64 . 1.238(2) ?
C64 N65 . 1.316(3) ?
C64 H64 . 0.9500 ?
N65 C66 . 1.445(3) ?
N65 C67 . 1.455(3) ?
C66 H66A . 0.9800 ?
C66 H66B . 0.9800 ?
C66 H66C . 0.9800 ?
C67 H67A . 0.9800 ?
C67 H67B . 0.9800 ?
C67 H67C . 0.9800 ?
O68 C69 . 1.225(3) ?
C69 N70 . 1.323(3) ?
C69 H69 . 0.9500 ?
N70 C72 . 1.441(3) ?
N70 C71 . 1.454(3) ?
C71 H71A . 0.9800 ?
C71 H71B . 0.9800 ?
C71 H71C . 0.9800 ?
C72 H72A . 0.9800 ?
C72 H72B . 0.9800 ?
C72 H72C . 0.9800 ?
O73 H73A . 0.8887 ?
O73 H73B . 0.8919 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O31 H31 O53 . 0.84 1.87 2.6891(18) 166
O38 H38 O73 . 0.84 1.88 2.720(2) 175
O45 H45 O58 . 0.84 1.82 2.649(2) 168
O52 H52 O63 . 0.84 1.80 2.6356(19) 176
O73 H73B O68 . 0.89 1.89 2.779(2) 180
O73 H73A O58 1_565 0.89 2.01 2.896(2) 180
