#------------------------------------------------------------------------------
#$Date: 2021-06-03 22:49:09 +0300 (Thu, 03 Jun 2021) $
#$Revision: 265732 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/87/4518772.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_4518772
loop_
_publ_author_name
'Zeng, Ziyu'
'Kociok-Köhn, Gabriele'
'Woodman, Timothy J.'
'Rowan, Michael G.'
'Blagbrough, Ian S.'
_publ_section_title
;
 The ¹H NMR Spectroscopic Effect of Steric Compression Is Found
 in [3.3.1]Oxa- and Azabicycles and Their Analogues.
;
_journal_issue                   19
_journal_name_full               'ACS omega'
_journal_page_first              12769
_journal_page_last               12786
_journal_paper_doi               10.1021/acsomega.1c01093
_journal_volume                  6
_journal_year                    2021
_chemical_formula_moiety         'C19 H25 N5 O6'
_chemical_formula_sum            'C19 H25 N5 O6'
_chemical_formula_weight         419.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                100.206(3)
_cell_angle_beta                 99.075(3)
_cell_angle_gamma                102.165(2)
_cell_formula_units_Z            4
_cell_length_a                   8.2535(2)
_cell_length_b                   14.1548(4)
_cell_length_c                   18.1606(7)
_cell_measurement_reflns_used    5495
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      71.9730
_cell_measurement_theta_min      3.2670
_cell_volume                     1998.79(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'
_computing_publication_material
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_computing_structure_refinement
;
 SHELXL-2016/6 (Sheldrick, 2016)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_structure_solution
; 
 SHELXT
 Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1150
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22201
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.332
_diffrn_reflns_theta_min         3.273
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.883
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_description       plate
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     553
_refine_ls_number_reflns         7805
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0674P)²+0.3895P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1369
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5895
_reflns_number_total             7805
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao1c01093_si_004.cif
_cod_data_source_block           s17phar15
_cod_database_code               4518772
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.843
_shelx_estimated_absorpt_t_max   0.983
_oxdiff_exptl_absorpt_empirical_full_min 0.778
_oxdiff_exptl_absorpt_empirical_full_max 1.484
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1706(2) 0.41585(14) 0.11137(11) 0.0345(4) Uani 1 1 d . . . . .
N2 N -0.0674(2) 0.41297(12) 0.29571(10) 0.0289(4) Uani 1 1 d . . . . .
N3 N 0.0001(2) 0.38355(13) 0.35973(10) 0.0295(4) Uani 1 1 d . . . . .
H3 H 0.091(3) 0.3630(19) 0.3639(15) 0.040(7) Uiso 1 1 d . . . . .
N4 N 0.1485(2) 0.33947(13) 0.50300(11) 0.0355(4) Uani 1 1 d . . . . .
N5 N -0.3349(3) 0.40226(15) 0.60572(12) 0.0432(5) Uani 1 1 d . . . . .
O1 O -0.3278(2) 0.49590(15) 0.16405(13) 0.0602(5) Uani 1 1 d . . . . .
O2 O -0.0812(2) 0.59154(12) 0.23226(11) 0.0469(4) Uani 1 1 d . . . . .
O3 O 0.2249(2) 0.32918(13) 0.44940(10) 0.0419(4) Uani 1 1 d . . . . .
O4 O 0.2056(2) 0.32972(14) 0.56663(10) 0.0496(4) Uani 1 1 d . . . . .
O5 O -0.3013(3) 0.35736(16) 0.65532(12) 0.0595(5) Uani 1 1 d . . . . .
O6 O -0.4355(2) 0.45570(16) 0.60717(11) 0.0565(5) Uani 1 1 d . . . . .
C1 C 0.3483(3) 0.3691(2) 0.02073(16) 0.0494(6) Uani 1 1 d . . . . .
H1A H 0.257980 0.311138 -0.007035 0.074 Uiso 1 1 calc R U . . .
H1B H 0.421683 0.350314 0.060600 0.074 Uiso 1 1 calc R U . . .
H1C H 0.415129 0.394254 -0.014868 0.074 Uiso 1 1 calc R U . . .
C2 C 0.2719(3) 0.44807(19) 0.05662(16) 0.0452(6) Uani 1 1 d . . . . .
H2A H 0.363498 0.507166 0.083262 0.054 Uiso 1 1 calc R U . . .
H2B H 0.199106 0.467396 0.016028 0.054 Uiso 1 1 calc R U . . .
C3 C 0.2751(3) 0.42661(16) 0.18670(13) 0.0345(5) Uani 1 1 d . . . . .
H3A H 0.318364 0.497740 0.211374 0.041 Uiso 1 1 calc R U . . .
H3B H 0.373426 0.398154 0.181078 0.041 Uiso 1 1 calc R U . . .
C4 C 0.1711(2) 0.37344(14) 0.23698(12) 0.0281(4) Uani 1 1 d . . . . .
H4 H 0.241098 0.390341 0.289911 0.034 Uiso 1 1 calc R U . . .
C5 C 0.1271(3) 0.25921(15) 0.20853(13) 0.0327(4) Uani 1 1 d . . . . .
H5A H 0.194445 0.243636 0.169500 0.039 Uiso 1 1 calc R U . . .
H5B H 0.164747 0.230281 0.252071 0.039 Uiso 1 1 calc R U . . .
C6 C -0.0572(3) 0.20748(15) 0.17465(13) 0.0351(5) Uani 1 1 d . . . . .
H6A H -0.123872 0.218113 0.214791 0.042 Uiso 1 1 calc R U . . .
H6B H -0.066755 0.135428 0.160051 0.042 Uiso 1 1 calc R U . . .
C7 C -0.1364(3) 0.24093(16) 0.10493(13) 0.0372(5) Uani 1 1 d . . . . .
H7A H -0.229596 0.185501 0.073611 0.045 Uiso 1 1 calc R U . . .
H7B H -0.049996 0.254950 0.073606 0.045 Uiso 1 1 calc R U . . .
C8 C -0.2064(3) 0.33260(17) 0.12293(13) 0.0368(5) Uani 1 1 d . . . . .
H8A H -0.296560 0.316894 0.152114 0.044 Uiso 1 1 calc R U . . .
H8B H -0.260376 0.344745 0.073966 0.044 Uiso 1 1 calc R U . . .
C9 C -0.0794(3) 0.43006(16) 0.16827(13) 0.0313(4) Uani 1 1 d . . . . .
C10 C -0.1803(3) 0.50693(17) 0.18798(13) 0.0361(5) Uani 1 1 d . . . . .
C11 C -0.1644(4) 0.6702(2) 0.25072(18) 0.0590(8) Uani 1 1 d . . . . .
H11A H -0.214178 0.686839 0.203523 0.089 Uiso 1 1 calc R U . . .
H11B H -0.081692 0.728647 0.283123 0.089 Uiso 1 1 calc R U . . .
H11C H -0.253913 0.648357 0.278031 0.089 Uiso 1 1 calc R U . . .
C12 C 0.0446(3) 0.47228(18) 0.12035(14) 0.0401(5) Uani 1 1 d . . . . .
H12A H -0.019620 0.471668 0.069313 0.048 Uiso 1 1 calc R U . . .
H12B H 0.102128 0.541916 0.145439 0.048 Uiso 1 1 calc R U . . .
C13 C 0.0125(2) 0.40908(14) 0.24061(12) 0.0271(4) Uani 1 1 d . . . . .
C14 C -0.0804(3) 0.38570(14) 0.41900(12) 0.0287(4) Uani 1 1 d . . . . .
C15 C -0.0136(3) 0.36421(14) 0.48930(13) 0.0311(4) Uani 1 1 d . . . . .
C16 C -0.0978(3) 0.36831(15) 0.55003(13) 0.0341(5) Uani 1 1 d . . . . .
H16 H -0.051358 0.353209 0.596542 0.041 Uiso 1 1 calc R U . . .
C17 C -0.2491(3) 0.39462(15) 0.54125(13) 0.0356(5) Uani 1 1 d . . . . .
C18 C -0.3199(3) 0.41639(16) 0.47333(13) 0.0365(5) Uani 1 1 d . . . . .
H18 H -0.424954 0.434415 0.468641 0.044 Uiso 1 1 calc R U . . .
C19 C -0.2381(3) 0.41181(15) 0.41343(13) 0.0340(5) Uani 1 1 d . . . . .
H19 H -0.287679 0.426372 0.367226 0.041 Uiso 1 1 calc R U . . .
N6 N 0.6412(2) -0.00386(12) 0.89792(10) 0.0262(3) Uani 1 1 d . . . . .
N7 N 0.6809(2) 0.09693(12) 0.69906(10) 0.0298(4) Uani 1 1 d . . . . .
N8 N 0.5394(2) 0.10932(14) 0.65370(11) 0.0327(4) Uani 1 1 d . . . . .
H8 H 0.448(4) 0.114(2) 0.6702(16) 0.050(8) Uiso 1 1 d . . . . .
N9 N 0.2399(2) 0.12626(14) 0.55414(11) 0.0358(4) Uani 1 1 d . . . . .
N10 N 0.5708(2) 0.17380(13) 0.36062(10) 0.0325(4) Uani 1 1 d . . . . .
O7 O 1.0895(2) 0.09845(13) 0.77527(11) 0.0463(4) Uani 1 1 d . . . . .
O8 O 0.89395(18) -0.04114(11) 0.72084(9) 0.0329(3) Uani 1 1 d . . . . .
O9 O 0.2297(2) 0.12796(15) 0.62113(10) 0.0474(4) Uani 1 1 d . . . . .
O10 O 0.1149(2) 0.11823(15) 0.50395(10) 0.0475(4) Uani 1 1 d . . . . .
O11 O 0.4534(2) 0.19866(13) 0.32588(9) 0.0425(4) Uani 1 1 d . . . . .
O12 O 0.7008(2) 0.16848(14) 0.33648(10) 0.0444(4) Uani 1 1 d . . . . .
C21 C 0.7616(3) -0.07792(19) 1.00129(14) 0.0416(5) Uani 1 1 d . . . . .
H21A H 0.847647 -0.101330 0.976708 0.062 Uiso 1 1 calc R U . . .
H21B H 0.726782 -0.120184 1.036145 0.062 Uiso 1 1 calc R U . . .
H21C H 0.808706 -0.009508 1.030118 0.062 Uiso 1 1 calc R U . . .
C22 C 0.6099(3) -0.08212(15) 0.94097(12) 0.0322(4) Uani 1 1 d . . . . .
H22A H 0.578507 -0.147414 0.904976 0.039 Uiso 1 1 calc R U . . .
H22B H 0.512968 -0.075933 0.965800 0.039 Uiso 1 1 calc R U . . .
C23 C 0.4845(2) -0.00723(15) 0.84587(12) 0.0297(4) Uani 1 1 d . . . . .
H23A H 0.397027 0.002082 0.876132 0.036 Uiso 1 1 calc R U . . .
H23B H 0.444160 -0.073619 0.811372 0.036 Uiso 1 1 calc R U . . .
C24 C 0.5040(2) 0.07155(15) 0.79725(12) 0.0305(4) Uani 1 1 d . . . . .
H24 H 0.406462 0.048123 0.752678 0.037 Uiso 1 1 calc R U . . .
C25 C 0.4947(3) 0.17509(17) 0.83713(14) 0.0388(5) Uani 1 1 d . . . . .
H25A H 0.489960 0.216357 0.798535 0.047 Uiso 1 1 calc R U . . .
H25B H 0.387309 0.168388 0.855777 0.047 Uiso 1 1 calc R U . . .
C26 C 0.6383(3) 0.22983(17) 0.90351(14) 0.0412(5) Uani 1 1 d . . . . .
H26A H 0.639172 0.190752 0.943643 0.049 Uiso 1 1 calc R U . . .
H26B H 0.615748 0.293876 0.925277 0.049 Uiso 1 1 calc R U . . .
C27 C 0.8133(3) 0.25002(15) 0.88372(14) 0.0383(5) Uani 1 1 d . . . . .
H27A H 0.803272 0.269283 0.833690 0.046 Uiso 1 1 calc R U . . .
H27B H 0.887533 0.307474 0.922294 0.046 Uiso 1 1 calc R U . . .
C28 C 0.9001(3) 0.16492(15) 0.87965(13) 0.0327(4) Uani 1 1 d . . . . .
H28A H 0.907625 0.145134 0.929464 0.039 Uiso 1 1 calc R U . . .
H28B H 1.017436 0.190551 0.873636 0.039 Uiso 1 1 calc R U . . .
C29 C 0.8189(2) 0.06999(14) 0.81582(11) 0.0255(4) Uani 1 1 d . . . . .
C30 C 0.9501(2) 0.04706(15) 0.76860(12) 0.0290(4) Uani 1 1 d . . . . .
C31 C 1.0152(3) -0.07147(18) 0.67842(13) 0.0373(5) Uani 1 1 d . . . . .
H31A H 0.969584 -0.140236 0.650137 0.056 Uiso 1 1 calc R U . . .
H31B H 1.120921 -0.066187 0.713884 0.056 Uiso 1 1 calc R U . . .
H31C H 1.037247 -0.028558 0.642446 0.056 Uiso 1 1 calc R U . . .
C32 C 0.7682(2) -0.01878(15) 0.85290(11) 0.0273(4) Uani 1 1 d . . . . .
H32A H 0.722595 -0.080047 0.812594 0.033 Uiso 1 1 calc R U . . .
H32B H 0.869373 -0.026782 0.886174 0.033 Uiso 1 1 calc R U . . .
C33 C 0.6621(2) 0.07939(14) 0.76449(11) 0.0268(4) Uani 1 1 d . . . . .
C34 C 0.5456(3) 0.12092(14) 0.58202(12) 0.0289(4) Uani 1 1 d . . . . .
C35 C 0.4027(2) 0.13278(15) 0.53216(12) 0.0294(4) Uani 1 1 d . . . . .
C36 C 0.4113(2) 0.14902(14) 0.46034(12) 0.0293(4) Uani 1 1 d . . . . .
H36 H 0.315499 0.158611 0.428728 0.035 Uiso 1 1 calc R U . . .
C37 C 0.5594(3) 0.15124(14) 0.43474(12) 0.0280(4) Uani 1 1 d . . . . .
C38 C 0.6997(3) 0.13426(14) 0.47944(12) 0.0296(4) Uani 1 1 d . . . . .
H38 H 0.799490 0.132667 0.459867 0.036 Uiso 1 1 calc R U . . .
C39 C 0.6931(3) 0.11993(15) 0.55154(12) 0.0309(4) Uani 1 1 d . . . . .
H39 H 0.789460 0.109078 0.581824 0.037 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C12 N1 C3 108.15(18) . . ?
C12 N1 C2 111.05(17) . . ?
C3 N1 C2 112.08(18) . . ?
C13 N2 N3 117.09(17) . . ?
C14 N3 N2 119.18(17) . . ?
C14 N3 H3 117.5(18) . . ?
N2 N3 H3 123.3(18) . . ?
O4 N4 O3 122.29(19) . . ?
O4 N4 C15 118.96(19) . . ?
O3 N4 C15 118.74(18) . . ?
O5 N5 O6 124.0(2) . . ?
O5 N5 C17 118.5(2) . . ?
O6 N5 C17 117.4(2) . . ?
C10 O2 C11 115.7(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C1 112.5(2) . . ?
N1 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
N1 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
N1 C3 C4 110.25(17) . . ?
N1 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
N1 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C13 C4 C3 110.59(16) . . ?
C13 C4 C5 110.54(16) . . ?
C3 C4 C5 111.71(17) . . ?
C13 C4 H4 108.0 . . ?
C3 C4 H4 108.0 . . ?
C5 C4 H4 108.0 . . ?
C6 C5 C4 117.20(17) . . ?
C6 C5 H5A 108.0 . . ?
C4 C5 H5A 108.0 . . ?
C6 C5 H5B 108.0 . . ?
C4 C5 H5B 108.0 . . ?
H5A C5 H5B 107.2 . . ?
C5 C6 C7 115.48(18) . . ?
C5 C6 H6A 108.4 . . ?
C7 C6 H6A 108.4 . . ?
C5 C6 H6B 108.4 . . ?
C7 C6 H6B 108.4 . . ?
H6A C6 H6B 107.5 . . ?
C6 C7 C8 115.18(19) . . ?
C6 C7 H7A 108.5 . . ?
C8 C7 H7A 108.5 . . ?
C6 C7 H7B 108.5 . . ?
C8 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C7 C8 C9 117.25(18) . . ?
C7 C8 H8A 108.0 . . ?
C9 C8 H8A 108.0 . . ?
C7 C8 H8B 108.0 . . ?
C9 C8 H8B 108.0 . . ?
H8A C8 H8B 107.2 . . ?
C13 C9 C10 110.51(18) . . ?
C13 C9 C12 111.83(17) . . ?
C10 C9 C12 106.91(17) . . ?
C13 C9 C8 107.79(16) . . ?
C10 C9 C8 107.85(17) . . ?
C12 C9 C8 111.88(19) . . ?
O1 C10 O2 123.2(2) . . ?
O1 C10 C9 124.9(2) . . ?
O2 C10 C9 111.82(19) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C9 111.90(17) . . ?
N1 C12 H12A 109.2 . . ?
C9 C12 H12A 109.2 . . ?
N1 C12 H12B 109.2 . . ?
C9 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
N2 C13 C4 127.15(18) . . ?
N2 C13 C9 114.43(17) . . ?
C4 C13 C9 117.86(17) . . ?
N3 C14 C15 123.04(19) . . ?
N3 C14 C19 120.3(2) . . ?
C15 C14 C19 116.65(19) . . ?
C16 C15 C14 122.0(2) . . ?
C16 C15 N4 115.96(19) . . ?
C14 C15 N4 122.02(19) . . ?
C17 C16 C15 118.6(2) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C16 C17 C18 121.6(2) . . ?
C16 C17 N5 118.7(2) . . ?
C18 C17 N5 119.7(2) . . ?
C19 C18 C17 120.0(2) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C14 121.2(2) . . ?
C18 C19 H19 119.4 . . ?
C14 C19 H19 119.4 . . ?
C32 N6 C23 108.44(15) . . ?
C32 N6 C22 110.20(15) . . ?
C23 N6 C22 109.42(16) . . ?
C33 N7 N8 115.84(17) . . ?
C34 N8 N7 119.29(18) . . ?
C34 N8 H8 117.6(19) . . ?
N7 N8 H8 122.9(19) . . ?
O9 N9 O10 122.17(19) . . ?
O9 N9 C35 119.67(18) . . ?
O10 N9 C35 118.16(19) . . ?
O11 N10 O12 123.29(19) . . ?
O11 N10 C37 118.77(18) . . ?
O12 N10 C37 117.92(18) . . ?
C30 O8 C31 114.79(16) . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N6 C22 C21 112.78(18) . . ?
N6 C22 H22A 109.0 . . ?
C21 C22 H22A 109.0 . . ?
N6 C22 H22B 109.0 . . ?
C21 C22 H22B 109.0 . . ?
H22A C22 H22B 107.8 . . ?
N6 C23 C24 113.62(16) . . ?
N6 C23 H23A 108.8 . . ?
C24 C23 H23A 108.8 . . ?
N6 C23 H23B 108.8 . . ?
C24 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C33 C24 C23 112.29(16) . . ?
C33 C24 C25 109.78(17) . . ?
C23 C24 C25 115.20(18) . . ?
C33 C24 H24 106.3 . . ?
C23 C24 H24 106.3 . . ?
C25 C24 H24 106.3 . . ?
C26 C25 C24 116.29(18) . . ?
C26 C25 H25A 108.2 . . ?
C24 C25 H25A 108.2 . . ?
C26 C25 H25B 108.2 . . ?
C24 C25 H25B 108.2 . . ?
H25A C25 H25B 107.4 . . ?
C25 C26 C27 115.0(2) . . ?
C25 C26 H26A 108.5 . . ?
C27 C26 H26A 108.5 . . ?
C25 C26 H26B 108.5 . . ?
C27 C26 H26B 108.5 . . ?
H26A C26 H26B 107.5 . . ?
C28 C27 C26 116.21(18) . . ?
C28 C27 H27A 108.2 . . ?
C26 C27 H27A 108.2 . . ?
C28 C27 H27B 108.2 . . ?
C26 C27 H27B 108.2 . . ?
H27A C27 H27B 107.4 . . ?
C27 C28 C29 118.05(18) . . ?
C27 C28 H28A 107.8 . . ?
C29 C28 H28A 107.8 . . ?
C27 C28 H28B 107.8 . . ?
C29 C28 H28B 107.8 . . ?
H28A C28 H28B 107.1 . . ?
C33 C29 C30 110.45(16) . . ?
C33 C29 C32 108.28(15) . . ?
C30 C29 C32 106.92(15) . . ?
C33 C29 C28 112.23(16) . . ?
C30 C29 C28 109.59(16) . . ?
C32 C29 C28 109.22(17) . . ?
O7 C30 O8 122.92(19) . . ?
O7 C30 C29 125.6(2) . . ?
O8 C30 C29 111.42(16) . . ?
O8 C31 H31A 109.5 . . ?
O8 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O8 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N6 C32 C29 110.55(15) . . ?
N6 C32 H32A 109.5 . . ?
C29 C32 H32A 109.5 . . ?
N6 C32 H32B 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 108.1 . . ?
N7 C33 C24 127.32(18) . . ?
N7 C33 C29 116.06(17) . . ?
C24 C33 C29 116.56(17) . . ?
N8 C34 C39 121.82(19) . . ?
N8 C34 C35 121.80(19) . . ?
C39 C34 C35 116.36(19) . . ?
C36 C35 C34 121.82(19) . . ?
C36 C35 N9 116.47(18) . . ?
C34 C35 N9 121.70(19) . . ?
C37 C36 C35 119.33(19) . . ?
C37 C36 H36 120.3 . . ?
C35 C36 H36 120.3 . . ?
C36 C37 C38 121.12(19) . . ?
C36 C37 N10 119.14(18) . . ?
C38 C37 N10 119.73(18) . . ?
C39 C38 C37 119.77(19) . . ?
C39 C38 H38 120.1 . . ?
C37 C38 H38 120.1 . . ?
C38 C39 C34 121.43(18) . . ?
C38 C39 H39 119.3 . . ?
C34 C39 H39 119.3 . . ?
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
N1 C12 1.450(3) . ?
N1 C3 1.462(3) . ?
N1 C2 1.469(3) . ?
N2 C13 1.282(3) . ?
N2 N3 1.379(2) . ?
N3 C14 1.350(3) . ?
N3 H3 0.85(3) . ?
N4 O4 1.220(3) . ?
N4 O3 1.245(2) . ?
N4 C15 1.449(3) . ?
N5 O5 1.221(3) . ?
N5 O6 1.235(3) . ?
N5 C17 1.461(3) . ?
O1 C10 1.193(3) . ?
O2 C10 1.337(3) . ?
O2 C11 1.444(3) . ?
C1 C2 1.496(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.535(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C13 1.506(3) . ?
C4 C5 1.553(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.518(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.529(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.533(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.548(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C13 1.519(3) . ?
C9 C10 1.531(3) . ?
C9 C12 1.539(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 C15 1.419(3) . ?
C14 C19 1.420(3) . ?
C15 C16 1.392(3) . ?
C16 C17 1.370(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.393(3) . ?
C18 C19 1.367(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N6 C32 1.454(2) . ?
N6 C23 1.463(3) . ?
N6 C22 1.468(2) . ?
N7 C33 1.282(3) . ?
N7 N8 1.381(2) . ?
N8 C34 1.348(3) . ?
N8 H8 0.87(3) . ?
N9 O9 1.229(3) . ?
N9 O10 1.235(2) . ?
N9 C35 1.451(3) . ?
N10 O11 1.221(2) . ?
N10 O12 1.233(2) . ?
N10 C37 1.450(3) . ?
O7 C30 1.200(3) . ?
O8 C30 1.331(3) . ?
O8 C31 1.444(2) . ?
C21 C22 1.511(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.539(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C33 1.509(3) . ?
C24 C25 1.539(3) . ?
C24 H24 1.0000 . ?
C25 C26 1.513(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.524(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.523(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.556(3) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C33 1.515(3) . ?
C29 C30 1.535(3) . ?
C29 C32 1.541(3) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C34 C39 1.416(3) . ?
C34 C35 1.428(3) . ?
C35 C36 1.374(3) . ?
C36 C37 1.371(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.396(3) . ?
C38 C39 1.368(3) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
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
N3 H3 O3 0.85(3) 1.95(3) 2.604(2) 132(2) .
N8 H8 O9 0.87(3) 1.94(3) 2.610(2) 133(3) .
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 N2 N3 C14 -179.52(18) . . . . ?
C12 N1 C2 C1 -155.7(2) . . . . ?
C3 N1 C2 C1 83.2(3) . . . . ?
C12 N1 C3 C4 68.6(2) . . . . ?
C2 N1 C3 C4 -168.67(18) . . . . ?
N1 C3 C4 C13 -54.2(2) . . . . ?
N1 C3 C4 C5 69.4(2) . . . . ?
C13 C4 C5 C6 12.3(3) . . . . ?
C3 C4 C5 C6 -111.3(2) . . . . ?
C4 C5 C6 C7 59.3(3) . . . . ?
C5 C6 C7 C8 -85.0(2) . . . . ?
C6 C7 C8 C9 61.2(3) . . . . ?
C7 C8 C9 C13 -53.7(3) . . . . ?
C7 C8 C9 C10 -173.02(19) . . . . ?
C7 C8 C9 C12 69.7(2) . . . . ?
C11 O2 C10 O1 0.7(4) . . . . ?
C11 O2 C10 C9 177.1(2) . . . . ?
C13 C9 C10 O1 -126.0(3) . . . . ?
C12 C9 C10 O1 112.1(3) . . . . ?
C8 C9 C10 O1 -8.4(3) . . . . ?
C13 C9 C10 O2 57.7(2) . . . . ?
C12 C9 C10 O2 -64.2(2) . . . . ?
C8 C9 C10 O2 175.33(18) . . . . ?
C3 N1 C12 C9 -64.9(2) . . . . ?
C2 N1 C12 C9 171.8(2) . . . . ?
C13 C9 C12 N1 47.1(3) . . . . ?
C10 C9 C12 N1 168.2(2) . . . . ?
C8 C9 C12 N1 -73.9(2) . . . . ?
N3 N2 C13 C4 1.5(3) . . . . ?
N3 N2 C13 C9 172.74(16) . . . . ?
C3 C4 C13 N2 -150.8(2) . . . . ?
C5 C4 C13 N2 85.0(2) . . . . ?
C3 C4 C13 C9 38.3(2) . . . . ?
C5 C4 C13 C9 -85.9(2) . . . . ?
C10 C9 C13 N2 34.1(2) . . . . ?
C12 C9 C13 N2 153.13(18) . . . . ?
C8 C9 C13 N2 -83.5(2) . . . . ?
C10 C9 C13 C4 -153.79(18) . . . . ?
C12 C9 C13 C4 -34.8(2) . . . . ?
C8 C9 C13 C4 88.6(2) . . . . ?
N2 N3 C14 C15 -174.95(17) . . . . ?
N2 N3 C14 C19 4.0(3) . . . . ?
N3 C14 C15 C16 179.05(19) . . . . ?
C19 C14 C15 C16 0.0(3) . . . . ?
N3 C14 C15 N4 0.9(3) . . . . ?
C19 C14 C15 N4 -178.15(18) . . . . ?
O4 N4 C15 C16 -4.3(3) . . . . ?
O3 N4 C15 C16 175.94(19) . . . . ?
O4 N4 C15 C14 174.0(2) . . . . ?
O3 N4 C15 C14 -5.8(3) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
N4 C15 C16 C17 177.85(18) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C15 C16 C17 N5 -177.95(18) . . . . ?
O5 N5 C17 C16 -22.3(3) . . . . ?
O6 N5 C17 C16 156.4(2) . . . . ?
O5 N5 C17 C18 159.3(2) . . . . ?
O6 N5 C17 C18 -22.0(3) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
N5 C17 C18 C19 178.35(19) . . . . ?
C17 C18 C19 C14 -0.4(3) . . . . ?
N3 C14 C19 C18 -178.7(2) . . . . ?
C15 C14 C19 C18 0.4(3) . . . . ?
C33 N7 N8 C34 -175.28(18) . . . . ?
C32 N6 C22 C21 66.1(2) . . . . ?
C23 N6 C22 C21 -174.77(18) . . . . ?
C32 N6 C23 C24 -59.2(2) . . . . ?
C22 N6 C23 C24 -179.46(17) . . . . ?
N6 C23 C24 C33 44.4(2) . . . . ?
N6 C23 C24 C25 -82.2(2) . . . . ?
C33 C24 C25 C26 -60.9(3) . . . . ?
C23 C24 C25 C26 67.1(3) . . . . ?
C24 C25 C26 C27 60.3(3) . . . . ?
C25 C26 C27 C28 -81.6(3) . . . . ?
C26 C27 C28 C29 65.4(3) . . . . ?
C27 C28 C29 C33 1.7(3) . . . . ?
C27 C28 C29 C30 124.8(2) . . . . ?
C27 C28 C29 C32 -118.4(2) . . . . ?
C31 O8 C30 O7 1.1(3) . . . . ?
C31 O8 C30 C29 -175.54(16) . . . . ?
C33 C29 C30 O7 118.3(2) . . . . ?
C32 C29 C30 O7 -124.1(2) . . . . ?
C28 C29 C30 O7 -5.8(3) . . . . ?
C33 C29 C30 O8 -65.1(2) . . . . ?
C32 C29 C30 O8 52.5(2) . . . . ?
C28 C29 C30 O8 170.78(16) . . . . ?
C23 N6 C32 C29 67.6(2) . . . . ?
C22 N6 C32 C29 -172.64(17) . . . . ?
C33 C29 C32 N6 -60.0(2) . . . . ?
C30 C29 C32 N6 -179.01(15) . . . . ?
C28 C29 C32 N6 62.5(2) . . . . ?
N8 N7 C33 C24 -0.4(3) . . . . ?
N8 N7 C33 C29 -177.53(16) . . . . ?
C23 C24 C33 N7 144.2(2) . . . . ?
C25 C24 C33 N7 -86.2(3) . . . . ?
C23 C24 C33 C29 -38.7(2) . . . . ?
C25 C24 C33 C29 90.9(2) . . . . ?
C30 C29 C33 N7 -20.2(2) . . . . ?
C32 C29 C33 N7 -136.91(18) . . . . ?
C28 C29 C33 N7 102.5(2) . . . . ?
C30 C29 C33 C24 162.43(16) . . . . ?
C32 C29 C33 C24 45.7(2) . . . . ?
C28 C29 C33 C24 -75.0(2) . . . . ?
N7 N8 C34 C39 0.6(3) . . . . ?
N7 N8 C34 C35 179.20(18) . . . . ?
N8 C34 C35 C36 177.05(19) . . . . ?
C39 C34 C35 C36 -4.2(3) . . . . ?
N8 C34 C35 N9 -4.3(3) . . . . ?
C39 C34 C35 N9 174.46(18) . . . . ?
O9 N9 C35 C36 -168.2(2) . . . . ?
O10 N9 C35 C36 12.4(3) . . . . ?
O9 N9 C35 C34 13.0(3) . . . . ?
O10 N9 C35 C34 -166.4(2) . . . . ?
C34 C35 C36 C37 1.8(3) . . . . ?
N9 C35 C36 C37 -176.92(18) . . . . ?
C35 C36 C37 C38 2.0(3) . . . . ?
C35 C36 C37 N10 -176.63(18) . . . . ?
O11 N10 C37 C36 6.3(3) . . . . ?
O12 N10 C37 C36 -174.96(19) . . . . ?
O11 N10 C37 C38 -172.35(19) . . . . ?
O12 N10 C37 C38 6.4(3) . . . . ?
C36 C37 C38 C39 -3.2(3) . . . . ?
N10 C37 C38 C39 175.37(18) . . . . ?
C37 C38 C39 C34 0.6(3) . . . . ?
N8 C34 C39 C38 -178.32(19) . . . . ?
C35 C34 C39 C38 3.0(3) . . . . ?
