#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/48/2104877.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_2104877
loop_
_publ_author_name
'Budesinsky, Milos'
'Cisarova, Ivana'
'Podlaha, Jaroslav'
'Borremans, Frans'
'Martins, José C.'
'Waroquier, Michel'
'Pauwels, Ewald'
_publ_section_title
;
 Structures of cyclic dipeptides: an X-ray and computational study of
 cis- and trans-cyclo(Pip-Phe),
 cyclo(Pro-Phe) and their N-methyl derivatives
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              662
_journal_page_last               677
_journal_paper_doi               10.1107/S0108768110040243
_journal_volume                  66
_journal_year                    2010
_chemical_formula_moiety         'C15 H18 N2 O2'
_chemical_formula_sum            'C15 H18 N2 O2'
_chemical_formula_weight         258.31
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.2660(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   22.1154(7)
_cell_length_b                   6.3963(2)
_cell_length_c                   29.5771(7)
_cell_measurement_reflns_used    62657
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      1
_cell_volume                     4166.2(2)
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_collection
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction        'COLLECT and DENZO'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0795
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            64641
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         1.20
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1656
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.231
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1051
_refine_ls_number_reflns         14267
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.1122
_refine_ls_R_factor_gt           0.0656
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0145P)²+2.6049P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1441
_reflns_number_gt                9326
_reflns_number_total             14267
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            so5040.cif
_cod_data_source_block           1b
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2104877
_cod_database_fobs_code          2104877
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
N N11 -0.18810(13) 0.4965(5) 0.85758(8) 0.0257(7) Uani d . 1 . .
C C12 -0.18332(15) 0.3068(6) 0.87631(11) 0.0266(8) Uani d . 1 . .
C C13 -0.20288(15) 0.2767(6) 0.92324(11) 0.0294(8) Uani d . 1 . .
H H13 -0.2279 0.1501 0.9224 0.035 Uiso calc R 1 . .
N N14 -0.23990(13) 0.4468(5) 0.93812(9) 0.0261(7) Uani d . 1 . .
C C15 -0.24115(15) 0.6423(6) 0.92199(10) 0.0224(8) Uani d . 1 . .
C C16 -0.21632(15) 0.6804(5) 0.87695(10) 0.0226(8) Uani d . 1 . .
H H16 -0.1851 0.7891 0.8815 0.027 Uiso calc R 1 . .
C C17 -0.26619(16) 0.7631(6) 0.84289(10) 0.0316(9) Uani d . 1 . .
H H17A -0.2813 0.8938 0.8541 0.038 Uiso calc R 1 . .
H H17B -0.2996 0.6641 0.8403 0.038 Uiso calc R 1 . .
C C18 -0.24460(18) 0.7995(7) 0.79582(10) 0.0389(10) Uani d . 1 . .
H H18A -0.2791 0.8352 0.7745 0.047 Uiso calc R 1 . .
H H18B -0.2164 0.9159 0.7971 0.047 Uiso calc R 1 . .
C C19 -0.21369(17) 0.6048(6) 0.77938(10) 0.0334(9) Uani d . 1 . .
H H19A -0.2432 0.4931 0.7744 0.040 Uiso calc R 1 . .
H H19B -0.1972 0.6343 0.7508 0.040 Uiso calc R 1 . .
C C110 -0.16345(16) 0.5370(6) 0.81404(10) 0.0342(9) Uani d . 1 . .
H H11A -0.1445 0.4112 0.8037 0.041 Uiso calc R 1 . .
H H11B -0.1328 0.6455 0.8178 0.041 Uiso calc R 1 . .
C C111 -0.14745(17) 0.2368(6) 0.95717(12) 0.0358(10) Uani d . 1 . .
H H11C -0.1609 0.1986 0.9863 0.043 Uiso calc R 1 . .
H H11D -0.1242 0.1209 0.9466 0.043 Uiso calc R 1 . .
C C112 -0.10734(17) 0.4284(6) 0.96277(11) 0.0316(9) Uani d . 1 . .
C C113 -0.11505(18) 0.5732(6) 0.99712(11) 0.0362(10) Uani d . 1 . .
H H113 -0.1440 0.5490 1.0174 0.043 Uiso calc R 1 . .
C C114 -0.07991(19) 0.7526(7) 1.00123(13) 0.0452(11) Uani d . 1 . .
H H114 -0.0856 0.8481 1.0242 0.054 Uiso calc R 1 . .
C C115 -0.03683(18) 0.7906(8) 0.97175(13) 0.0479(11) Uani d . 1 . .
H H115 -0.0135 0.9116 0.9749 0.057 Uiso calc R 1 . .
C C116 -0.02788(19) 0.6531(7) 0.93795(14) 0.0449(11) Uani d . 1 . .
H H116 0.0019 0.6786 0.9184 0.054 Uiso calc R 1 . .
C C117 -0.06381(17) 0.4729(6) 0.93275(12) 0.0362(9) Uani d . 1 . .
H H117 -0.0586 0.3814 0.9090 0.043 Uiso calc R 1 . .
O O12 -0.16021(12) 0.1581(4) 0.85792(8) 0.0409(7) Uani d . 1 . .
O O15 -0.26457(11) 0.7900(4) 0.94108(7) 0.0331(6) Uani d . 1 . .
N N21 0.29507(15) 0.4846(5) 0.87566(9) 0.0348(8) Uani d . 1 . .
C C22 0.30010(17) 0.2900(6) 0.89185(12) 0.0348(9) Uani d . 1 . .
C C23 0.29341(17) 0.2573(6) 0.94162(11) 0.0358(9) Uani d . 1 . .
H H23 0.2670 0.1361 0.9448 0.043 Uiso calc R 1 . .
N N24 0.26790(14) 0.4365(5) 0.96412(10) 0.0303(7) Uani d . 1 . .
C C25 0.26370(16) 0.6314(6) 0.94829(11) 0.0295(9) Uani d . 1 . .
C C26 0.27089(17) 0.6661(6) 0.89841(10) 0.0301(9) Uani d . 1 . .
H H26 0.2997 0.7814 0.8963 0.036 Uiso calc R 1 . .
C C27 0.21073(19) 0.7328(7) 0.87301(12) 0.0459(11) Uani d . 1 . .
H H27A 0.1808 0.6234 0.8755 0.055 Uiso calc R 1 . .
H H27B 0.1961 0.8581 0.8870 0.055 Uiso calc R 1 . .
C C28 0.2173(2) 0.7755(8) 0.82307(12) 0.0520(11) Uani d . 1 . .
H H28A 0.2413 0.9011 0.8203 0.062 Uiso calc R 1 . .
H H28B 0.1775 0.7995 0.8073 0.062 Uiso calc R 1 . .
C C29 0.2479(2) 0.5920(8) 0.80068(12) 0.0520(12) Uani d . 1 . .
H H29A 0.2204 0.4736 0.7981 0.062 Uiso calc R 1 . .
H H29B 0.2567 0.6318 0.7703 0.062 Uiso calc R 1 . .
C C210 0.3064(2) 0.5295(7) 0.82815(11) 0.0491(12) Uani d . 1 . .
H H21A 0.3231 0.4063 0.8148 0.059 Uiso calc R 1 . .
H H21B 0.3358 0.6417 0.8275 0.059 Uiso calc R 1 . .
C C211 0.35748(18) 0.2066(6) 0.96520(13) 0.0415(10) Uani d . 1 . .
H H21C 0.3544 0.1856 0.9974 0.050 Uiso calc R 1 . .
H H21D 0.3718 0.0771 0.9529 0.050 Uiso calc R 1 . .
C C212 0.40331(17) 0.3767(6) 0.95916(12) 0.0357(9) Uani d . 1 . .
C C213 0.41134(18) 0.5452(7) 0.98971(13) 0.0431(11) Uani d . 1 . .
H H213 0.3894 0.5476 1.0150 0.052 Uiso calc R 1 . .
C C214 0.45009(18) 0.7039(7) 0.98330(15) 0.0496(12) Uani d . 1 . .
H H214 0.4556 0.8099 1.0048 0.060 Uiso calc R 1 . .
C C215 0.4813(2) 0.7095(8) 0.94532(15) 0.0545(12) Uani d . 1 . .
H H215 0.5065 0.8219 0.9403 0.065 Uiso calc R 1 . .
C C216 0.47507(18) 0.5480(8) 0.91497(15) 0.0504(12) Uani d . 1 . .
H H216 0.4969 0.5498 0.8896 0.061 Uiso calc R 1 . .
C C217 0.43610(18) 0.3795(7) 0.92158(13) 0.0425(10) Uani d . 1 . .
H H217 0.4324 0.2703 0.9007 0.051 Uiso calc R 1 . .
O O22 0.31394(14) 0.1389(4) 0.86910(8) 0.0468(7) Uani d . 1 . .
O O25 0.25042(12) 0.7827(4) 0.97130(8) 0.0419(7) Uani d . 1 . .
N N31 0.01837(13) -0.0103(5) 0.80175(9) 0.0286(7) Uani d . 1 . .
C C32 0.01465(16) -0.2023(6) 0.78399(11) 0.0320(9) Uani d . 1 . .
C C33 0.03689(17) -0.2353(6) 0.73809(11) 0.0346(9) Uani d . 1 . .
H H33 0.0618 -0.3622 0.7392 0.042 Uiso calc R 1 . .
N N34 0.07276(13) -0.0620(5) 0.72206(11) 0.0337(8) Uani d . 1 . .
C C35 0.07335(17) 0.1319(7) 0.73811(13) 0.0355(9) Uani d . 1 . .
C C36 0.04788(17) 0.1700(6) 0.78317(12) 0.0333(9) Uani d . 1 . .
H H36 0.0175 0.2813 0.7786 0.040 Uiso calc R 1 . .
C C37 0.09855(19) 0.2501(7) 0.81675(13) 0.0501(11) Uani d . 1 . .
H H37A 0.1138 0.3810 0.8058 0.060 Uiso calc R 1 . .
H H37B 0.1317 0.1501 0.8191 0.060 Uiso calc R 1 . .
C C38 0.0763(2) 0.2841(8) 0.86376(13) 0.0578(12) Uani d . 1 . .
H H38A 0.1107 0.3182 0.8852 0.069 Uiso calc R 1 . .
H H38B 0.0486 0.4020 0.8624 0.069 Uiso calc R 1 . .
C C39 0.04443(19) 0.0939(7) 0.88052(12) 0.0452(11) Uani d . 1 . .
H H39A 0.0278 0.1260 0.9090 0.054 Uiso calc R 1 . .
H H39B 0.0732 -0.0199 0.8858 0.054 Uiso calc R 1 . .
C C310 -0.00622(16) 0.0289(7) 0.84539(11) 0.0352(9) Uani d . 1 . .
H H31A -0.0256 -0.0969 0.8554 0.042 Uiso calc R 1 . .
H H31B -0.0366 0.1385 0.8418 0.042 Uiso calc R 1 . .
C C311 -0.01982(17) -0.2709(6) 0.70407(13) 0.0391(10) Uani d . 1 . .
H H31C -0.0066 -0.3152 0.6752 0.047 Uiso calc R 1 . .
H H31D -0.0439 -0.3831 0.7153 0.047 Uiso calc R 1 . .
C C312 -0.05872(16) -0.0815(6) 0.69664(12) 0.0327(9) Uani d . 1 . .
C C313 -0.04975(17) 0.0589(7) 0.66217(11) 0.0368(10) Uani d . 1 . .
H H313 -0.0204 0.0314 0.6424 0.044 Uiso calc R 1 . .
C C314 -0.08438(17) 0.2415(7) 0.65687(12) 0.0414(10) Uani d . 1 . .
H H314 -0.0780 0.3334 0.6334 0.050 Uiso calc R 1 . .
C C315 -0.12875(17) 0.2883(7) 0.68645(12) 0.0404(10) Uani d . 1 . .
H H315 -0.1515 0.4105 0.6833 0.049 Uiso calc R 1 . .
C C316 -0.13721(17) 0.1448(7) 0.72049(13) 0.0420(11) Uani d . 1 . .
H H316 -0.1667 0.1706 0.7403 0.050 Uiso calc R 1 . .
C C317 -0.10342(16) -0.0330(7) 0.72566(12) 0.0353(9) Uani d . 1 . .
H H317 -0.1102 -0.1246 0.7491 0.042 Uiso calc R 1 . .
O O32 -0.00871(12) -0.3519(4) 0.80245(9) 0.0451(7) Uani d . 1 . .
O O35 0.09600(12) 0.2802(5) 0.71901(9) 0.0472(7) Uani d . 1 . .
N N41 0.14268(17) 0.4798(5) 0.54158(10) 0.0427(9) Uani d . 1 . .
C C42 0.1474(2) 0.2896(7) 0.55880(12) 0.0455(11) Uani d . 1 . .
C C43 0.13511(18) 0.2563(6) 0.60750(12) 0.0381(10) Uani d . 1 . .
H H43 0.1088 0.1335 0.6086 0.046 Uiso calc R 1 . .
N N44 0.10430(16) 0.4312(6) 0.62625(13) 0.0458(9) Uani d . 1 . .
C C45 0.10235(17) 0.6251(7) 0.61046(13) 0.0382(10) Uani d . 1 . .
C C46 0.11788(18) 0.6616(6) 0.56288(12) 0.0377(10) Uani d . 1 . .
H H46 0.1481 0.7739 0.5635 0.045 Uiso calc R 1 . .
C C47 0.0613(2) 0.7334(9) 0.53346(18) 0.0833(18) Uani d . 1 . .
H H47A 0.0463 0.8620 0.5458 0.100 Uiso calc R 1 . .
H H47B 0.0298 0.6282 0.5342 0.100 Uiso calc R 1 . .
C C48 0.0752(3) 0.7704(10) 0.48347(15) 0.107(2) Uani d . 1 . .
H H48A 0.0375 0.7977 0.4649 0.129 Uiso calc R 1 . .
H H48B 0.1010 0.8925 0.4821 0.129 Uiso calc R 1 . .
C C49 0.1065(3) 0.5826(9) 0.46458(15) 0.094(2) Uani d . 1 . .
H H49A 0.0786 0.4656 0.4614 0.113 Uiso calc R 1 . .
H H49B 0.1188 0.6158 0.4348 0.113 Uiso calc R 1 . .
C C410 0.1612(2) 0.5239(7) 0.49581(12) 0.0606(14) Uani d . 1 . .
H H41A 0.1804 0.4012 0.4842 0.073 Uiso calc R 1 . .
H H41B 0.1904 0.6375 0.4974 0.073 Uiso calc R 1 . .
C C411 0.19496(19) 0.2079(7) 0.63580(12) 0.0445(11) Uani d . 1 . .
H H41C 0.1869 0.1772 0.6668 0.053 Uiso calc R 1 . .
H H41D 0.2135 0.0854 0.6236 0.053 Uiso calc R 1 . .
C C412 0.2383(2) 0.3910(7) 0.63552(13) 0.0484(11) Uani d . 1 . .
C C413 0.2380(2) 0.5455(8) 0.66754(17) 0.0698(15) Uani d . 1 . .
H H413 0.2127 0.5331 0.6908 0.084 Uiso calc R 1 . .
C C414 0.2749(4) 0.7205(11) 0.6657(3) 0.116(3) Uani d . 1 . .
H H414 0.2750 0.8251 0.6876 0.139 Uiso calc R 1 . .
C C415 0.3115(4) 0.7337(17) 0.6304(4) 0.169(7) Uani d . 1 . .
H H415 0.3369 0.8489 0.6287 0.203 Uiso calc R 1 . .
C C416 0.3115(3) 0.5898(17) 0.5993(4) 0.148(5) Uani d . 1 . .
H H416 0.3361 0.6064 0.5757 0.178 Uiso calc R 1 . .
C C417 0.2758(2) 0.4127(9) 0.60053(17) 0.0686(15) Uani d . 1 . .
H H417 0.2769 0.3099 0.5784 0.082 Uiso calc R 1 . .
O O42 0.16481(18) 0.1379(5) 0.53748(9) 0.0724(11) Uani d . 1 . .
O O45 0.08605(13) 0.7761(5) 0.63259(10) 0.0534(8) Uani d . 1 . .
N N51 0.54685(14) 0.9973(5) 0.79982(9) 0.0297(7) Uani d . 1 . .
C C52 0.54046(16) 0.8034(6) 0.78274(11) 0.0314(9) Uani d . 1 . .
C C53 0.54674(17) 0.7714(6) 0.73256(11) 0.0350(9) Uani d . 1 . .
H H53 0.5731 0.6497 0.7298 0.042 Uiso calc R 1 . .
N N54 0.57468(15) 0.9463(5) 0.71134(11) 0.0356(8) Uani d . 1 . .
C C55 0.57920(16) 1.1377(6) 0.72726(12) 0.0300(8) Uani d . 1 . .
C C56 0.56963(15) 1.1772(6) 0.77658(11) 0.0269(8) Uani d . 1 . .
H H56 0.5398 1.2900 0.7776 0.032 Uiso calc R 1 . .
C C57 0.62886(16) 1.2506(6) 0.80293(11) 0.0363(9) Uani d . 1 . .
H H57A 0.6427 1.3777 0.7892 0.044 Uiso calc R 1 . .
H H57B 0.6599 1.1447 0.8009 0.044 Uiso calc R 1 . .
C C58 0.62001(18) 1.2922(8) 0.85343(11) 0.0430(10) Uani d . 1 . .
H H58A 0.6593 1.3175 0.8700 0.052 Uiso calc R 1 . .
H H58B 0.5955 1.4169 0.8557 0.052 Uiso calc R 1 . .
C C59 0.58940(18) 1.1099(7) 0.87504(12) 0.0446(10) Uani d . 1 . .
H H59A 0.6174 0.9930 0.8786 0.053 Uiso calc R 1 . .
H H59B 0.5789 1.1502 0.9050 0.053 Uiso calc R 1 . .
C C510 0.53255(17) 1.0430(6) 0.84632(11) 0.0345(9) Uani d . 1 . .
H H51A 0.5157 0.9194 0.8594 0.041 Uiso calc R 1 . .
H H51B 0.5025 1.1535 0.8458 0.041 Uiso calc R 1 . .
C C511 0.48428(18) 0.7169(6) 0.70839(12) 0.0404(10) Uani d . 1 . .
H H51C 0.4882 0.6930 0.6764 0.048 Uiso calc R 1 . .
H H51D 0.4694 0.5891 0.7211 0.048 Uiso calc R 1 . .
C C512 0.43946(17) 0.8907(6) 0.71351(11) 0.0342(9) Uani d . 1 . .
C C513 0.40434(17) 0.8918(7) 0.75043(12) 0.0438(11) Uani d . 1 . .
H H513 0.4077 0.7808 0.7708 0.053 Uiso calc R 1 . .
C C514 0.3651(2) 1.0517(9) 0.75742(14) 0.0564(13) Uani d . 1 . .
H H514 0.3422 1.0491 0.7822 0.068 Uiso calc R 1 . .
C C515 0.3598(2) 1.2195(8) 0.72680(15) 0.0630(15) Uani d . 1 . .
H H515 0.3330 1.3281 0.7311 0.076 Uiso calc R 1 . .
C C516 0.3948(2) 1.2231(7) 0.69007(13) 0.0521(12) Uani d . 1 . .
H H516 0.3922 1.3355 0.6700 0.063 Uiso calc R 1 . .
C C517 0.43388(18) 1.0568(7) 0.68354(12) 0.0407(10) Uani d . 1 . .
H H517 0.4566 1.0577 0.6586 0.049 Uiso calc R 1 . .
O O52 0.52535(13) 0.6539(4) 0.80549(8) 0.0442(7) Uani d . 1 . .
O O55 0.59400(11) 1.2887(4) 0.70393(7) 0.0374(6) Uani d . 1 . .
N N61 0.63307(16) 1.5006(5) 0.52701(10) 0.0417(9) Uani d . 1 . .
C C62 0.6388(2) 1.3085(6) 0.54377(12) 0.0399(10) Uani d . 1 . .
C C63 0.62485(17) 1.2716(6) 0.59232(10) 0.0334(9) Uani d . 1 . .
H H63 0.5997 1.1458 0.5932 0.040 Uiso calc R 1 . .
N N64 0.59291(13) 1.4456(5) 0.61204(10) 0.0289(7) Uani d . 1 . .
C C65 0.58960(17) 1.6417(6) 0.59598(11) 0.0305(9) Uani d . 1 . .
C C66 0.6057(2) 1.6791(6) 0.54838(11) 0.0412(10) Uani d . 1 . .
H H66 0.6358 1.7920 0.5500 0.049 Uiso calc R 1 . .
C C67 0.5504(2) 1.7574(8) 0.51850(12) 0.0595(13) Uani d . 1 . .
H H67A 0.5181 1.6548 0.5185 0.071 Uiso calc R 1 . .
H H67B 0.5360 1.8863 0.5311 0.071 Uiso calc R 1 . .
C C68 0.5648(3) 1.7964(9) 0.46969(13) 0.0777(17) Uani d . 1 . .
H H68A 0.5274 1.8249 0.4510 0.093 Uiso calc R 1 . .
H H68B 0.5905 1.9190 0.4689 0.093 Uiso calc R 1 . .
C C69 0.5967(3) 1.6107(8) 0.44989(13) 0.0708(16) Uani d . 1 . .
H H69A 0.5686 1.4944 0.4457 0.085 Uiso calc R 1 . .
H H69B 0.6094 1.6484 0.4205 0.085 Uiso calc R 1 . .
C C610 0.6515(2) 1.5452(8) 0.48114(12) 0.0605(14) Uani d . 1 . .
H H61A 0.6696 1.4214 0.4691 0.073 Uiso calc R 1 . .
H H61B 0.6815 1.6561 0.4829 0.073 Uiso calc R 1 . .
C C611 0.68619(17) 1.2310(6) 0.62093(11) 0.0346(9) Uani d . 1 . .
H H61C 0.6782 1.1936 0.6516 0.042 Uiso calc R 1 . .
H H61D 0.7063 1.1133 0.6081 0.042 Uiso calc R 1 . .
C C612 0.72766(16) 1.4161(7) 0.62273(12) 0.0359(10) Uani d . 1 . .
C C613 0.72413(17) 1.5683(7) 0.65572(14) 0.0414(10) Uani d . 1 . .
H H613 0.6962 1.5535 0.6772 0.050 Uiso calc R 1 . .
C C614 0.7611(2) 1.7403(8) 0.65714(16) 0.0583(13) Uani d . 1 . .
H H614 0.7594 1.8382 0.6802 0.070 Uiso calc R 1 . .
C C615 0.8011(2) 1.7688(9) 0.62438(19) 0.0697(15) Uani d . 1 . .
H H615 0.8250 1.8884 0.6245 0.084 Uiso calc R 1 . .
C C616 0.80500(19) 1.6173(10) 0.59150(18) 0.0635(15) Uani d . 1 . .
H H616 0.8325 1.6336 0.5698 0.076 Uiso calc R 1 . .
C C617 0.76855(18) 1.4424(8) 0.59059(14) 0.0497(12) Uani d . 1 . .
H H617 0.7715 1.3416 0.5682 0.060 Uiso calc R 1 . .
O O62 0.65854(16) 1.1591(5) 0.52299(9) 0.0589(9) Uani d . 1 . .
O O65 0.57063(11) 1.7889(4) 0.61750(8) 0.0388(6) Uani d . 1 . .
H H14 -0.2546(19) 0.457(7) 0.9612(14) 0.061(15) Uiso d . 1 . .
H H24 0.262(2) 0.412(7) 0.9929(15) 0.072(15) Uiso d . 1 . .
H H34 0.0930(16) -0.086(6) 0.6935(12) 0.043(11) Uiso d . 1 . .
H H44 0.0995(15) 0.418(6) 0.6525(11) 0.021(10) Uiso d . 1 . .
H H54 0.5730(13) 0.935(5) 0.6824(11) 0.015(8) Uiso d . 1 . .
H H64 0.5802(16) 1.415(6) 0.6415(12) 0.041(11) Uiso d . 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
C12 N11 C110 . . 120.2(3) ?
C12 N11 C16 . . 125.8(3) ?
C110 N11 C16 . . 113.9(3) ?
O12 C12 N11 . . 122.7(3) ?
O12 C12 C13 . . 118.4(3) ?
N11 C12 C13 . . 118.8(3) ?
N14 C13 C12 . . 113.7(3) ?
N14 C13 C111 . . 111.4(3) ?
C12 C13 C111 . . 110.2(3) ?
N14 C13 H13 . . 107.1 ?
C12 C13 H13 . . 107.1 ?
C111 C13 H13 . . 107.1 ?
C15 N14 C13 . . 125.8(3) ?
C15 N14 H14 . . 104(4) ?
C13 N14 H14 . . 128(3) ?
O15 C15 N14 . . 123.1(3) ?
O15 C15 C16 . . 118.8(3) ?
N14 C15 C16 . . 118.0(3) ?
N11 C16 C15 . . 114.6(3) ?
N11 C16 C17 . . 109.2(3) ?
C15 C16 C17 . . 110.0(3) ?
N11 C16 H16 . . 107.6 ?
C15 C16 H16 . . 107.6 ?
C17 C16 H16 . . 107.6 ?
C16 C17 C18 . . 112.8(3) ?
C16 C17 H17A . . 109.0 ?
C18 C17 H17A . . 109.0 ?
C16 C17 H17B . . 109.0 ?
C18 C17 H17B . . 109.0 ?
H17A C17 H17B . . 107.8 ?
C19 C18 C17 . . 110.7(3) ?
C19 C18 H18A . . 109.5 ?
C17 C18 H18A . . 109.5 ?
C19 C18 H18B . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 108.1 ?
C110 C19 C18 . . 110.1(3) ?
C110 C19 H19A . . 109.6 ?
C18 C19 H19A . . 109.6 ?
C110 C19 H19B . . 109.6 ?
C18 C19 H19B . . 109.6 ?
H19A C19 H19B . . 108.2 ?
N11 C110 C19 . . 109.8(3) ?
N11 C110 H11A . . 109.7 ?
C19 C110 H11A . . 109.7 ?
N11 C110 H11B . . 109.7 ?
C19 C110 H11B . . 109.7 ?
H11A C110 H11B . . 108.2 ?
C112 C111 C13 . . 111.3(3) ?
C112 C111 H11C . . 109.4 ?
C13 C111 H11C . . 109.4 ?
C112 C111 H11D . . 109.4 ?
C13 C111 H11D . . 109.4 ?
H11C C111 H11D . . 108.0 ?
C113 C112 C117 . . 117.7(4) ?
C113 C112 C111 . . 120.5(3) ?
C117 C112 C111 . . 121.8(3) ?
C114 C113 C112 . . 120.6(4) ?
C114 C113 H113 . . 119.7 ?
C112 C113 H113 . . 119.7 ?
C115 C114 C113 . . 120.6(4) ?
C115 C114 H114 . . 119.7 ?
C113 C114 H114 . . 119.7 ?
C116 C115 C114 . . 120.6(4) ?
C116 C115 H115 . . 119.7 ?
C114 C115 H115 . . 119.7 ?
C115 C116 C117 . . 119.6(4) ?
C115 C116 H116 . . 120.2 ?
C117 C116 H116 . . 120.2 ?
C112 C117 C116 . . 121.0(4) ?
C112 C117 H117 . . 119.5 ?
C116 C117 H117 . . 119.5 ?
C22 N21 C26 . . 126.5(3) ?
C22 N21 C210 . . 120.4(3) ?
C26 N21 C210 . . 112.5(3) ?
O22 C22 N21 . . 123.5(3) ?
O22 C22 C23 . . 118.4(4) ?
N21 C22 C23 . . 117.8(3) ?
N24 C23 C22 . . 114.3(3) ?
N24 C23 C211 . . 109.4(3) ?
C22 C23 C211 . . 107.5(3) ?
N24 C23 H23 . . 108.5 ?
C22 C23 H23 . . 108.5 ?
C211 C23 H23 . . 108.5 ?
C25 N24 C23 . . 126.2(3) ?
C25 N24 H24 . . 120(3) ?
C23 N24 H24 . . 113(3) ?
O25 C25 N24 . . 123.6(3) ?
O25 C25 C26 . . 118.3(3) ?
N24 C25 C26 . . 118.0(3) ?
N21 C26 C25 . . 113.9(3) ?
N21 C26 C27 . . 109.4(3) ?
C25 C26 C27 . . 110.8(3) ?
N21 C26 H26 . . 107.4 ?
C25 C26 H26 . . 107.4 ?
C27 C26 H26 . . 107.4 ?
C28 C27 C26 . . 111.8(3) ?
C28 C27 H27A . . 109.3 ?
C26 C27 H27A . . 109.3 ?
C28 C27 H27B . . 109.3 ?
C26 C27 H27B . . 109.3 ?
H27A C27 H27B . . 107.9 ?
C27 C28 C29 . . 111.5(4) ?
C27 C28 H28A . . 109.3 ?
C29 C28 H28A . . 109.3 ?
C27 C28 H28B . . 109.3 ?
C29 C28 H28B . . 109.3 ?
H28A C28 H28B . . 108.0 ?
C210 C29 C28 . . 111.0(3) ?
C210 C29 H29A . . 109.4 ?
C28 C29 H29A . . 109.4 ?
C210 C29 H29B . . 109.4 ?
C28 C29 H29B . . 109.4 ?
H29A C29 H29B . . 108.0 ?
N21 C210 C29 . . 110.5(3) ?
N21 C210 H21A . . 109.5 ?
C29 C210 H21A . . 109.5 ?
N21 C210 H21B . . 109.5 ?
C29 C210 H21B . . 109.5 ?
H21A C210 H21B . . 108.1 ?
C212 C211 C23 . . 113.0(3) ?
C212 C211 H21C . . 109.0 ?
C23 C211 H21C . . 109.0 ?
C212 C211 H21D . . 109.0 ?
C23 C211 H21D . . 109.0 ?
H21C C211 H21D . . 107.8 ?
C217 C212 C213 . . 117.5(4) ?
C217 C212 C211 . . 120.8(4) ?
C213 C212 C211 . . 121.5(3) ?
C214 C213 C212 . . 121.9(4) ?
C214 C213 H213 . . 119.0 ?
C212 C213 H213 . . 119.0 ?
C213 C214 C215 . . 120.5(4) ?
C213 C214 H214 . . 119.8 ?
C215 C214 H214 . . 119.8 ?
C216 C215 C214 . . 119.3(4) ?
C216 C215 H215 . . 120.3 ?
C214 C215 H215 . . 120.3 ?
C215 C216 C217 . . 121.0(4) ?
C215 C216 H216 . . 119.5 ?
C217 C216 H216 . . 119.5 ?
C212 C217 C216 . . 119.7(4) ?
C212 C217 H217 . . 120.1 ?
C216 C217 H217 . . 120.1 ?
C32 N31 C36 . . 126.4(3) ?
C32 N31 C310 . . 119.2(3) ?
C36 N31 C310 . . 114.3(3) ?
O32 C32 N31 . . 123.4(3) ?
O32 C32 C33 . . 118.4(4) ?
N31 C32 C33 . . 118.1(3) ?
N34 C33 C32 . . 114.7(3) ?
N34 C33 C311 . . 109.3(3) ?
C32 C33 C311 . . 107.1(3) ?
N34 C33 H33 . . 108.5 ?
C32 C33 H33 . . 108.5 ?
C311 C33 H33 . . 108.5 ?
C35 N34 C33 . . 125.3(3) ?
C35 N34 H34 . . 117(2) ?
C33 N34 H34 . . 117(2) ?
O35 C35 N34 . . 123.1(3) ?
O35 C35 C36 . . 118.6(4) ?
N34 C35 C36 . . 118.2(3) ?
N31 C36 C35 . . 114.8(3) ?
N31 C36 C37 . . 110.5(3) ?
C35 C36 C37 . . 108.6(3) ?
N31 C36 H36 . . 107.6 ?
C35 C36 H36 . . 107.6 ?
C37 C36 H36 . . 107.6 ?
C36 C37 C38 . . 111.3(3) ?
C36 C37 H37A . . 109.4 ?
C38 C37 H37A . . 109.4 ?
C36 C37 H37B . . 109.4 ?
C38 C37 H37B . . 109.4 ?
H37A C37 H37B . . 108.0 ?
C39 C38 C37 . . 112.4(4) ?
C39 C38 H38A . . 109.1 ?
C37 C38 H38A . . 109.1 ?
C39 C38 H38B . . 109.1 ?
C37 C38 H38B . . 109.1 ?
H38A C38 H38B . . 107.9 ?
C38 C39 C310 . . 109.5(3) ?
C38 C39 H39A . . 109.8 ?
C310 C39 H39A . . 109.8 ?
C38 C39 H39B . . 109.8 ?
C310 C39 H39B . . 109.8 ?
H39A C39 H39B . . 108.2 ?
N31 C310 C39 . . 109.9(3) ?
N31 C310 H31A . . 109.7 ?
C39 C310 H31A . . 109.7 ?
N31 C310 H31B . . 109.7 ?
C39 C310 H31B . . 109.7 ?
H31A C310 H31B . . 108.2 ?
C312 C311 C33 . . 113.4(3) ?
C312 C311 H31C . . 108.9 ?
C33 C311 H31C . . 108.9 ?
C312 C311 H31D . . 108.9 ?
C33 C311 H31D . . 108.9 ?
H31C C311 H31D . . 107.7 ?
C313 C312 C317 . . 117.6(4) ?
C313 C312 C311 . . 121.0(3) ?
C317 C312 C311 . . 121.3(4) ?
C312 C313 C314 . . 120.7(3) ?
C312 C313 H313 . . 119.7 ?
C314 C313 H313 . . 119.7 ?
C313 C314 C315 . . 121.0(4) ?
C313 C314 H314 . . 119.5 ?
C315 C314 H314 . . 119.5 ?
C316 C315 C314 . . 117.3(4) ?
C316 C315 H315 . . 121.3 ?
C314 C315 H315 . . 121.3 ?
C317 C316 C315 . . 121.7(4) ?
C317 C316 H316 . . 119.2 ?
C315 C316 H316 . . 119.2 ?
C316 C317 C312 . . 121.8(4) ?
C316 C317 H317 . . 119.1 ?
C312 C317 H317 . . 119.1 ?
C42 N41 C46 . . 126.2(3) ?
C42 N41 C410 . . 120.7(3) ?
C46 N41 C410 . . 113.1(3) ?
O42 C42 N41 . . 122.9(4) ?
O42 C42 C43 . . 118.0(4) ?
N41 C42 C43 . . 119.0(4) ?
N44 C43 C42 . . 113.0(4) ?
N44 C43 C411 . . 111.1(3) ?
C42 C43 C411 . . 109.2(3) ?
N44 C43 H43 . . 107.8 ?
C42 C43 H43 . . 107.8 ?
C411 C43 H43 . . 107.8 ?
C45 N44 C43 . . 126.2(3) ?
C45 N44 H44 . . 116(3) ?
C43 N44 H44 . . 113(3) ?
O45 C45 N44 . . 123.1(4) ?
O45 C45 C46 . . 118.5(4) ?
N44 C45 C46 . . 118.3(4) ?
N41 C46 C45 . . 114.3(3) ?
N41 C46 C47 . . 108.4(3) ?
C45 C46 C47 . . 109.6(4) ?
N41 C46 H46 . . 108.1 ?
C45 C46 H46 . . 108.1 ?
C47 C46 H46 . . 108.1 ?
C46 C47 C48 . . 111.3(5) ?
C46 C47 H47A . . 109.4 ?
C48 C47 H47A . . 109.4 ?
C46 C47 H47B . . 109.4 ?
C48 C47 H47B . . 109.4 ?
H47A C47 H47B . . 108.0 ?
C49 C48 C47 . . 111.5(5) ?
C49 C48 H48A . . 109.3 ?
C47 C48 H48A . . 109.3 ?
C49 C48 H48B . . 109.3 ?
C47 C48 H48B . . 109.3 ?
H48A C48 H48B . . 108.0 ?
C410 C49 C48 . . 109.9(4) ?
C410 C49 H49A . . 109.7 ?
C48 C49 H49A . . 109.7 ?
C410 C49 H49B . . 109.7 ?
C48 C49 H49B . . 109.7 ?
H49A C49 H49B . . 108.2 ?
N41 C410 C49 . . 109.6(4) ?
N41 C410 H41A . . 109.7 ?
C49 C410 H41A . . 109.7 ?
N41 C410 H41B . . 109.7 ?
C49 C410 H41B . . 109.7 ?
H41A C410 H41B . . 108.2 ?
C412 C411 C43 . . 110.9(3) ?
C412 C411 H41C . . 109.5 ?
C43 C411 H41C . . 109.5 ?
C412 C411 H41D . . 109.5 ?
C43 C411 H41D . . 109.5 ?
H41C C411 H41D . . 108.0 ?
C413 C412 C417 . . 119.0(5) ?
C413 C412 C411 . . 120.7(4) ?
C417 C412 C411 . . 120.1(5) ?
C412 C413 C414 . . 121.0(6) ?
C412 C413 H413 . . 119.5 ?
C414 C413 H413 . . 119.5 ?
C415 C414 C413 . . 117.7(8) ?
C415 C414 H414 . . 121.1 ?
C413 C414 H414 . . 121.1 ?
C416 C415 C414 . . 121.9(10) ?
C416 C415 H415 . . 119.1 ?
C414 C415 H415 . . 119.1 ?
C415 C416 C417 . . 121.7(10) ?
C415 C416 H416 . . 119.1 ?
C417 C416 H416 . . 119.1 ?
C416 C417 C412 . . 118.7(7) ?
C416 C417 H417 . . 120.6 ?
C412 C417 H417 . . 120.6 ?
C52 N51 C56 . . 125.6(3) ?
C52 N51 C510 . . 120.8(3) ?
C56 N51 C510 . . 113.5(3) ?
O52 C52 N51 . . 122.4(3) ?
O52 C52 C53 . . 118.9(4) ?
N51 C52 C53 . . 118.5(3) ?
N54 C53 C52 . . 113.6(3) ?
N54 C53 C511 . . 112.0(3) ?
C52 C53 C511 . . 109.1(3) ?
N54 C53 H53 . . 107.3 ?
C52 C53 H53 . . 107.3 ?
C511 C53 H53 . . 107.3 ?
C55 N54 C53 . . 125.9(3) ?
C55 N54 H54 . . 115(2) ?
C53 N54 H54 . . 113(2) ?
O55 C55 N54 . . 122.6(3) ?
O55 C55 C56 . . 118.0(3) ?
N54 C55 C56 . . 119.3(3) ?
N51 C56 C55 . . 114.1(3) ?
N51 C56 C57 . . 108.6(3) ?
C55 C56 C57 . . 110.6(3) ?
N51 C56 H56 . . 107.8 ?
C55 C56 H56 . . 107.8 ?
C57 C56 H56 . . 107.8 ?
C56 C57 C58 . . 111.4(3) ?
C56 C57 H57A . . 109.3 ?
C58 C57 H57A . . 109.3 ?
C56 C57 H57B . . 109.3 ?
C58 C57 H57B . . 109.3 ?
H57A C57 H57B . . 108.0 ?
C59 C58 C57 . . 112.0(4) ?
C59 C58 H58A . . 109.2 ?
C57 C58 H58A . . 109.2 ?
C59 C58 H58B . . 109.2 ?
C57 C58 H58B . . 109.2 ?
H58A C58 H58B . . 107.9 ?
C510 C59 C58 . . 111.1(3) ?
C510 C59 H59A . . 109.4 ?
C58 C59 H59A . . 109.4 ?
C510 C59 H59B . . 109.4 ?
C58 C59 H59B . . 109.4 ?
H59A C59 H59B . . 108.0 ?
N51 C510 C59 . . 110.1(3) ?
N51 C510 H51A . . 109.7 ?
C59 C510 H51A . . 109.7 ?
N51 C510 H51B . . 109.7 ?
C59 C510 H51B . . 109.7 ?
H51A C510 H51B . . 108.2 ?
C512 C511 C53 . . 111.0(3) ?
C512 C511 H51C . . 109.4 ?
C53 C511 H51C . . 109.4 ?
C512 C511 H51D . . 109.4 ?
C53 C511 H51D . . 109.4 ?
H51C C511 H51D . . 108.0 ?
C517 C512 C513 . . 118.3(4) ?
C517 C512 C511 . . 121.6(3) ?
C513 C512 C511 . . 120.0(4) ?
C514 C513 C512 . . 121.8(4) ?
C514 C513 H513 . . 119.1 ?
C512 C513 H513 . . 119.1 ?
C513 C514 C515 . . 119.4(4) ?
C513 C514 H514 . . 120.3 ?
C515 C514 H514 . . 120.3 ?
C516 C515 C514 . . 119.9(4) ?
C516 C515 H515 . . 120.1 ?
C514 C515 H515 . . 120.1 ?
C515 C516 C517 . . 119.4(4) ?
C515 C516 H516 . . 120.3 ?
C517 C516 H516 . . 120.3 ?
C512 C517 C516 . . 121.1(4) ?
C512 C517 H517 . . 119.4 ?
C516 C517 H517 . . 119.4 ?
C62 N61 C66 . . 126.2(3) ?
C62 N61 C610 . . 119.8(4) ?
C66 N61 C610 . . 113.9(3) ?
O62 C62 N61 . . 123.7(3) ?
O62 C62 C63 . . 117.5(4) ?
N61 C62 C63 . . 118.6(3) ?
N64 C63 C62 . . 113.9(3) ?
N64 C63 C611 . . 109.8(3) ?
C62 C63 C611 . . 107.4(3) ?
N64 C63 H63 . . 108.5 ?
C62 C63 H63 . . 108.5 ?
C611 C63 H63 . . 108.5 ?
C65 N64 C63 . . 125.5(3) ?
C65 N64 H64 . . 120(2) ?
C63 N64 H64 . . 113(2) ?
O65 C65 N64 . . 122.8(3) ?
O65 C65 C66 . . 118.9(3) ?
N64 C65 C66 . . 118.1(3) ?
N61 C66 C65 . . 115.1(3) ?
N61 C66 C67 . . 110.3(3) ?
C65 C66 C67 . . 110.3(4) ?
N61 C66 H66 . . 106.9 ?
C65 C66 H66 . . 106.9 ?
C67 C66 H66 . . 106.9 ?
C68 C67 C66 . . 112.0(4) ?
C68 C67 H67A . . 109.2 ?
C66 C67 H67A . . 109.2 ?
C68 C67 H67B . . 109.2 ?
C66 C67 H67B . . 109.2 ?
H67A C67 H67B . . 107.9 ?
C69 C68 C67 . . 112.3(4) ?
C69 C68 H68A . . 109.1 ?
C67 C68 H68A . . 109.1 ?
C69 C68 H68B . . 109.1 ?
C67 C68 H68B . . 109.1 ?
H68A C68 H68B . . 107.9 ?
C610 C69 C68 . . 110.7(4) ?
C610 C69 H69A . . 109.5 ?
C68 C69 H69A . . 109.5 ?
C610 C69 H69B . . 109.5 ?
C68 C69 H69B . . 109.5 ?
H69A C69 H69B . . 108.1 ?
N61 C610 C69 . . 109.9(4) ?
N61 C610 H61A . . 109.7 ?
C69 C610 H61A . . 109.7 ?
N61 C610 H61B . . 109.7 ?
C69 C610 H61B . . 109.7 ?
H61A C610 H61B . . 108.2 ?
C612 C611 C63 . . 112.9(3) ?
C612 C611 H61C . . 109.0 ?
C63 C611 H61C . . 109.0 ?
C612 C611 H61D . . 109.0 ?
C63 C611 H61D . . 109.0 ?
H61C C611 H61D . . 107.8 ?
C617 C612 C613 . . 118.8(4) ?
C617 C612 C611 . . 120.7(4) ?
C613 C612 C611 . . 120.5(3) ?
C614 C613 C612 . . 120.9(4) ?
C614 C613 H613 . . 119.5 ?
C612 C613 H613 . . 119.5 ?
C613 C614 C615 . . 120.2(5) ?
C613 C614 H614 . . 119.9 ?
C615 C614 H614 . . 119.9 ?
C616 C615 C614 . . 119.1(5) ?
C616 C615 H615 . . 120.4 ?
C614 C615 H615 . . 120.4 ?
C617 C616 C615 . . 120.6(4) ?
C617 C616 H616 . . 119.7 ?
C615 C616 H616 . . 119.7 ?
C616 C617 C612 . . 120.3(5) ?
C616 C617 H617 . . 119.9 ?
C612 C617 H617 . . 119.9 ?
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
N11 C12 . 1.334(5) ?
N11 C110 . 1.467(4) ?
N11 C16 . 1.472(4) ?
C12 O12 . 1.230(4) ?
C12 C13 . 1.504(4) ?
C13 N14 . 1.454(5) ?
C13 C111 . 1.533(5) ?
C13 H13 . 0.9800 ?
N14 C15 . 1.338(5) ?
N14 H14 . 0.79(4) ?
C15 O15 . 1.238(4) ?
C15 C16 . 1.507(4) ?
C16 C17 . 1.519(5) ?
C16 H16 . 0.9800 ?
C17 C18 . 1.531(4) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 C19 . 1.522(5) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C19 C110 . 1.505(5) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C110 H11A . 0.9700 ?
C110 H11B . 0.9700 ?
C111 C112 . 1.513(5) ?
C111 H11C . 0.9700 ?
C111 H11D . 0.9700 ?
C112 C113 . 1.397(5) ?
C112 C117 . 1.397(5) ?
C113 C114 . 1.385(6) ?
C113 H113 . 0.9300 ?
C114 C115 . 1.371(6) ?
C114 H114 . 0.9300 ?
C115 C116 . 1.360(6) ?
C115 H115 . 0.9300 ?
C116 C117 . 1.401(6) ?
C116 H116 . 0.9300 ?
C117 H117 . 0.9300 ?
N21 C22 . 1.335(5) ?
N21 C26 . 1.467(4) ?
N21 C210 . 1.478(4) ?
C22 O22 . 1.232(4) ?
C22 C23 . 1.507(5) ?
C23 N24 . 1.464(5) ?
C23 C211 . 1.555(5) ?
C23 H23 . 0.9800 ?
N24 C25 . 1.332(5) ?
N24 H24 . 0.89(4) ?
C25 O25 . 1.234(4) ?
C25 C26 . 1.515(4) ?
C26 C27 . 1.527(5) ?
C26 H26 . 0.9800 ?
C27 C28 . 1.522(5) ?
C27 H27A . 0.9700 ?
C27 H27B . 0.9700 ?
C28 C29 . 1.535(6) ?
C28 H28A . 0.9700 ?
C28 H28B . 0.9700 ?
C29 C210 . 1.516(6) ?
C29 H29A . 0.9700 ?
C29 H29B . 0.9700 ?
C210 H21A . 0.9700 ?
C210 H21B . 0.9700 ?
C211 C212 . 1.509(6) ?
C211 H21C . 0.9700 ?
C211 H21D . 0.9700 ?
C212 C217 . 1.382(5) ?
C212 C213 . 1.407(6) ?
C213 C214 . 1.353(6) ?
C213 H213 . 0.9300 ?
C214 C215 . 1.372(6) ?
C214 H214 . 0.9300 ?
C215 C216 . 1.367(6) ?
C215 H215 . 0.9300 ?
C216 C217 . 1.405(6) ?
C216 H216 . 0.9300 ?
C217 H217 . 0.9300 ?
N31 C32 . 1.335(5) ?
N31 C36 . 1.457(4) ?
N31 C310 . 1.467(4) ?
C32 O32 . 1.238(4) ?
C32 C33 . 1.501(5) ?
C33 N34 . 1.466(5) ?
C33 C311 . 1.551(5) ?
C33 H33 . 0.9800 ?
N34 C35 . 1.328(5) ?
N34 H34 . 1.00(4) ?
C35 O35 . 1.234(5) ?
C35 C36 . 1.514(5) ?
C36 C37 . 1.516(5) ?
C36 H36 . 0.9800 ?
C37 C38 . 1.533(5) ?
C37 H37A . 0.9700 ?
C37 H37B . 0.9700 ?
C38 C39 . 1.512(6) ?
C38 H38A . 0.9700 ?
C38 H38B . 0.9700 ?
C39 C310 . 1.515(5) ?
C39 H39A . 0.9700 ?
C39 H39B . 0.9700 ?
C310 H31A . 0.9700 ?
C310 H31B . 0.9700 ?
C311 C312 . 1.490(5) ?
C311 H31C . 0.9700 ?
C311 H31D . 0.9700 ?
C312 C313 . 1.387(5) ?
C312 C317 . 1.402(5) ?
C313 C314 . 1.397(6) ?
C313 H313 . 0.9300 ?
C314 C315 . 1.406(5) ?
C314 H314 . 0.9300 ?
C315 C316 . 1.388(6) ?
C315 H315 . 0.9300 ?
C316 C317 . 1.361(6) ?
C316 H316 . 0.9300 ?
C317 H317 . 0.9300 ?
N41 C42 . 1.319(5) ?
N41 C46 . 1.454(5) ?
N41 C410 . 1.478(5) ?
C42 O42 . 1.237(5) ?
C42 C43 . 1.505(5) ?
C43 N44 . 1.447(5) ?
C43 C411 . 1.531(5) ?
C43 H43 . 0.9800 ?
N44 C45 . 1.324(5) ?
N44 H44 . 0.80(3) ?
C45 O45 . 1.239(5) ?
C45 C46 . 1.497(5) ?
C46 C47 . 1.529(6) ?
C46 H46 . 0.9800 ?
C47 C48 . 1.556(7) ?
C47 H47A . 0.9700 ?
C47 H47B . 0.9700 ?
C48 C49 . 1.519(7) ?
C48 H48A . 0.9700 ?
C48 H48B . 0.9700 ?
C49 C410 . 1.501(7) ?
C49 H49A . 0.9700 ?
C49 H49B . 0.9700 ?
C410 H41A . 0.9700 ?
C410 H41B . 0.9700 ?
C411 C412 . 1.515(6) ?
C411 H41C . 0.9700 ?
C411 H41D . 0.9700 ?
C412 C413 . 1.369(7) ?
C412 C417 . 1.391(6) ?
C413 C414 . 1.389(8) ?
C413 H413 . 0.9300 ?
C414 C415 . 1.383(13) ?
C414 H414 . 0.9300 ?
C415 C416 . 1.300(15) ?
C415 H415 . 0.9300 ?
C416 C417 . 1.383(10) ?
C416 H416 . 0.9300 ?
C417 H417 . 0.9300 ?
N51 C52 . 1.342(5) ?
N51 C56 . 1.454(4) ?
N51 C510 . 1.469(4) ?
C52 O52 . 1.233(4) ?
C52 C53 . 1.517(5) ?
C53 N54 . 1.448(5) ?
C53 C511 . 1.536(5) ?
C53 H53 . 0.9800 ?
N54 C55 . 1.312(5) ?
N54 H54 . 0.86(3) ?
C55 O55 . 1.249(4) ?
C55 C56 . 1.514(5) ?
C56 C57 . 1.535(5) ?
C56 H56 . 0.9800 ?
C57 C58 . 1.547(5) ?
C57 H57A . 0.9700 ?
C57 H57B . 0.9700 ?
C58 C59 . 1.518(6) ?
C58 H58A . 0.9700 ?
C58 H58B . 0.9700 ?
C59 C510 . 1.513(5) ?
C59 H59A . 0.9700 ?
C59 H59B . 0.9700 ?
C510 H51A . 0.9700 ?
C510 H51B . 0.9700 ?
C511 C512 . 1.506(5) ?
C511 H51C . 0.9700 ?
C511 H51D . 0.9700 ?
C512 C517 . 1.382(5) ?
C512 C513 . 1.397(5) ?
C513 C514 . 1.369(6) ?
C513 H513 . 0.9300 ?
C514 C515 . 1.402(7) ?
C514 H514 . 0.9300 ?
C515 C516 . 1.390(6) ?
C515 H515 . 0.9300 ?
C516 C517 . 1.395(6) ?
C516 H516 . 0.9300 ?
C517 H517 . 0.9300 ?
N61 C62 . 1.327(5) ?
N61 C66 . 1.462(5) ?
N61 C610 . 1.480(5) ?
C62 O62 . 1.238(5) ?
C62 C63 . 1.514(5) ?
C63 N64 . 1.467(5) ?
C63 C611 . 1.553(5) ?
C63 H63 . 0.9800 ?
N64 C65 . 1.341(5) ?
N64 H64 . 0.96(4) ?
C65 O65 . 1.232(4) ?
C65 C66 . 1.503(5) ?
C66 C67 . 1.527(6) ?
C66 H66 . 0.9800 ?
C67 C68 . 1.527(6) ?
C67 H67A . 0.9700 ?
C67 H67B . 0.9700 ?
C68 C69 . 1.525(7) ?
C68 H68A . 0.9700 ?
C68 H68B . 0.9700 ?
C69 C610 . 1.514(7) ?
C69 H69A . 0.9700 ?
C69 H69B . 0.9700 ?
C610 H61A . 0.9700 ?
C610 H61B . 0.9700 ?
C611 C612 . 1.496(6) ?
C611 H61C . 0.9700 ?
C611 H61D . 0.9700 ?
C612 C617 . 1.381(5) ?
C612 C613 . 1.386(6) ?
C613 C614 . 1.369(6) ?
C613 H613 . 0.9300 ?
C614 C615 . 1.382(7) ?
C614 H614 . 0.9300 ?
C615 C616 . 1.381(7) ?
C615 H615 . 0.9300 ?
C616 C617 . 1.378(7) ?
C616 H616 . 0.9300 ?
C617 H617 . 0.9300 ?
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
N14 H14 O25 2_547 0.79(4) 2.28(4) 2.906(4) 137(4)
N24 H24 O15 2_547 0.89(4) 2.10(5) 2.964(4) 165(4)
N34 H34 O45 1_545 1.00(4) 2.00(4) 2.881(4) 145(3)
N44 H44 O35 . 0.80(3) 2.16(3) 2.930(5) 162(4)
N54 H54 O65 1_545 0.86(3) 2.13(3) 2.946(4) 159(3)
N64 H64 O55 . 0.96(4) 2.01(4) 2.895(4) 152(3)
