#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/76/2017607.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_2017607
loop_
_publ_author_name
'Sengar, Raghvendra Singh'
'Geib, Steven J.'
'Nigam, Archana'
'Wiener, Erik C.'
_publ_section_title
;
 Tri-tert-butyl
 3-oxo-4-oxa-1,8,11-triazaspiro[5.6]dodecane-1,8,11-triacetate
;
_journal_coeditor_code           FN3037
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o174
_journal_page_last               o175
_journal_paper_doi               10.1107/S0108270109049361
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C26 H45 N3 O8'
_chemical_formula_moiety         'C26 H45 N3 O8'
_chemical_formula_sum            'C26 H45 N3 O8'
_chemical_formula_weight         527.65
_chemical_name_systematic
;
Tri-tert-butyl
3-oxo-4-oxa-1,8,11-triazaspiro[5.6]dodecane-1,8,11-triacetate
;
_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                99.305(4)
_cell_angle_beta                 90.010(3)
_cell_angle_gamma                100.168(3)
_cell_formula_units_Z            4
_cell_length_a                   11.1304(17)
_cell_length_b                   15.250(2)
_cell_length_c                   18.098(3)
_cell_measurement_reflns_used    4387
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      24.72
_cell_measurement_theta_min      2.28
_cell_volume                     2982.6(8)
_computing_cell_refinement       'SMART (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_sigmaI/netI    0.0779
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21467
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  .980
_exptl_absorpt_correction_T_min  .962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.221
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     667
_refine_ls_number_reflns         11582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0606
_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)+(0.0780P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1539
_refine_ls_wR_factor_ref         0.1701
_reflns_number_gt                7769
_reflns_number_total             11582
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fn3037.cif
_cod_data_source_block           I
_cod_original_cell_volume        2982.5(8)
_cod_database_code               2017607
_cod_database_fobs_code          2017607
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
N N1 0.39731(16) 0.67232(12) 0.09461(9) 0.0377(4) Uani d . 1 . .
O O1 0.40064(15) 0.92475(12) 0.15327(10) 0.0543(5) Uani d . 1 . .
C C1 0.45976(19) 0.75264(14) 0.06693(11) 0.0347(5) Uani d . 1 . .
H H1A 0.3987 0.7843 0.0494 0.042 Uiso calc R 1 . .
H H1B 0.5085 0.7340 0.0240 0.042 Uiso calc R 1 . .
N N2 0.66007(15) 0.68993(12) 0.12598(9) 0.0350(4) Uani d . 1 . .
C C2 0.4616(2) 0.59587(15) 0.07647(13) 0.0452(6) Uani d . 1 . .
H H2A 0.4865 0.5914 0.0243 0.054 Uiso calc R 1 . .
H H2B 0.4059 0.5399 0.0815 0.054 Uiso calc R 1 . .
O O2 0.42055(18) 1.04161(13) 0.09357(13) 0.0813(7) Uani d . 1 . .
O O3 0.10887(13) 0.63734(11) -0.00927(7) 0.0422(4) Uani d . 1 . .
N N3 0.61348(15) 0.88656(12) 0.08799(10) 0.0386(4) Uani d . 1 . .
C C3 0.5738(2) 0.60575(15) 0.12716(13) 0.0445(6) Uani d . 1 . .
H H3A 0.5477 0.6034 0.1786 0.053 Uiso calc R 1 . .
H H3B 0.6155 0.5546 0.1115 0.053 Uiso calc R 1 . .
C C4 0.62026(18) 0.76784(14) 0.17081(11) 0.0333(5) Uani d . 1 . .
H H4A 0.6926 0.8104 0.1928 0.040 Uiso calc R 1 . .
H H4B 0.5720 0.7473 0.2121 0.040 Uiso calc R 1 . .
O O4 0.29145(15) 0.61343(14) -0.05496(9) 0.0609(5) Uani d . 1 . .
N N4 0.82517(18) 0.32138(13) 0.39869(10) 0.0437(5) Uani d . 1 . .
O O5 0.93958(13) 0.68547(10) 0.22990(7) 0.0386(4) Uani d . 1 . .
C C5 0.26748(19) 0.65231(17) 0.07875(11) 0.0418(5) Uani d . 1 . .
H H5A 0.2322 0.7038 0.1028 0.050 Uiso calc R 1 . .
H H5B 0.2327 0.6003 0.1022 0.050 Uiso calc R 1 . .
N N5 1.08196(17) 0.29854(13) 0.37395(9) 0.0397(4) Uani d . 1 . .
O O6 0.74587(15) 0.66414(14) 0.26987(9) 0.0579(5) Uani d . 1 . .
C C6 0.2270(2) 0.63181(16) -0.00387(12) 0.0395(5) Uani d . 1 . .
N N6 0.91778(16) 0.09754(12) 0.39427(10) 0.0384(4) Uani d . 1 . .
O O7 0.93936(12) 0.89762(10) 0.06443(8) 0.0381(4) Uani d . 1 . .
C C7 0.0418(2) 0.61897(17) -0.08259(12) 0.0438(6) Uani d . 1 . .
O O8 0.84142(13) 0.94627(11) 0.16839(8) 0.0464(4) Uani d . 1 . .
C C8 0.0965(3) 0.6853(2) -0.13176(14) 0.0663(8) Uani d . 1 . .
H H8A 0.0950 0.7463 -0.1065 0.099 Uiso calc R 1 . .
H H8B 0.0496 0.6739 -0.1786 0.099 Uiso calc R 1 . .
H H8C 0.1803 0.6786 -0.1419 0.099 Uiso calc R 1 . .
C C9 -0.0851(2) 0.6317(2) -0.05938(14) 0.0697(9) Uani d . 1 . .
H H9A -0.0831 0.6939 -0.0359 0.104 Uiso calc R 1 . .
H H9B -0.1143 0.5917 -0.0241 0.104 Uiso calc R 1 . .
H H9C -0.1395 0.6178 -0.1032 0.104 Uiso calc R 1 . .
O O9 0.70047(14) 0.07270(12) 0.31403(9) 0.0505(4) Uani d . 1 . .
C C10 0.0413(3) 0.52294(19) -0.11932(14) 0.0612(7) Uani d . 1 . .
H H10A 0.0039 0.4820 -0.0866 0.092 Uiso calc R 1 . .
H H10B 0.1245 0.5142 -0.1286 0.092 Uiso calc R 1 . .
H H10C -0.0049 0.5107 -0.1664 0.092 Uiso calc R 1 . .
O O10 0.64781(17) -0.05877(14) 0.35089(11) 0.0709(6) Uani d . 1 . .
C C11 0.78597(19) 0.68381(16) 0.14172(11) 0.0377(5) Uani d . 1 . .
H H11A 0.8386 0.7374 0.1286 0.045 Uiso calc R 1 . .
H H11B 0.8057 0.6311 0.1085 0.045 Uiso calc R 1 . .
O O11 0.55671(15) 0.35867(12) 0.50508(8) 0.0510(4) Uani d . 1 . .
C C12 0.8186(2) 0.67609(15) 0.22217(12) 0.0378(5) Uani d . 1 . .
O O12 0.74806(17) 0.36860(17) 0.54955(9) 0.0754(6) Uani d . 1 . .
C C13 0.9998(2) 0.68940(16) 0.30409(11) 0.0423(5) Uani d . 1 . .
O O13 1.36652(14) 0.30534(12) 0.27335(8) 0.0475(4) Uani d . 1 . .
C C14 0.9752(3) 0.7712(2) 0.35646(14) 0.0627(7) Uani d . 1 . .
H H14A 0.8894 0.7628 0.3684 0.094 Uiso calc R 1 . .
H H14B 0.9959 0.8242 0.3326 0.094 Uiso calc R 1 . .
H H14C 1.0243 0.7793 0.4021 0.094 Uiso calc R 1 . .
O O14 1.19095(17) 0.34162(14) 0.23709(9) 0.0601(5) Uani d . 1 . .
C C15 0.9594(2) 0.60264(18) 0.33431(13) 0.0553(7) Uani d . 1 . .
H H15A 0.8738 0.5969 0.3463 0.083 Uiso calc R 1 . .
H H15B 1.0075 0.6033 0.3792 0.083 Uiso calc R 1 . .
H H15C 0.9710 0.5519 0.2969 0.083 Uiso calc R 1 . .
O O15 1.23757(14) 0.08603(11) 0.42575(8) 0.0462(4) Uani d . 1 . .
C C16 1.1340(2) 0.7000(2) 0.28449(14) 0.0618(7) Uani d . 1 . .
H H16A 1.1477 0.6464 0.2510 0.093 Uiso calc R 1 . .
H H16B 1.1837 0.7078 0.3299 0.093 Uiso calc R 1 . .
H H16C 1.1560 0.7524 0.2600 0.093 Uiso calc R 1 . .
O O16 1.11896(16) 0.02944(15) 0.32270(10) 0.0677(6) Uani d . 1 . .
C C17 0.54374(18) 0.81800(14) 0.12679(11) 0.0328(5) Uani d . 1 . .
C C18 0.4664(2) 0.86554(17) 0.18453(13) 0.0457(6) Uani d . 1 . .
H H18A 0.4081 0.8200 0.2048 0.055 Uiso calc R 1 . .
H H18B 0.5197 0.9006 0.2261 0.055 Uiso calc R 1 . .
C C19 0.4689(2) 0.98670(18) 0.11756(16) 0.0564(7) Uani d . 1 . .
C C20 0.6003(2) 0.97978(16) 0.11063(14) 0.0480(6) Uani d . 1 . .
H H20A 0.6369 1.0158 0.0735 0.058 Uiso calc R 1 . .
H H20B 0.6434 1.0040 0.1588 0.058 Uiso calc R 1 . .
C C21 0.72624(18) 0.87247(15) 0.05463(11) 0.0365(5) Uani d . 1 . .
H H21A 0.7340 0.8998 0.0090 0.044 Uiso calc R 1 . .
H H21B 0.7226 0.8074 0.0395 0.044 Uiso calc R 1 . .
C C22 0.84106(18) 0.91027(15) 0.10394(12) 0.0350(5) Uani d . 1 . .
C C23 1.06572(18) 0.92773(16) 0.09735(12) 0.0382(5) Uani d . 1 . .
C C24 1.0815(2) 0.87568(17) 0.16025(13) 0.0480(6) Uani d . 1 . .
H H24A 1.0315 0.8943 0.2018 0.072 Uiso calc R 1 . .
H H24B 1.1665 0.8879 0.1768 0.072 Uiso calc R 1 . .
H H24C 1.0564 0.8115 0.1424 0.072 Uiso calc R 1 . .
C C25 1.1422(2) 0.89998(19) 0.03137(13) 0.0518(6) Uani d . 1 . .
H H25A 1.1307 0.9340 -0.0082 0.078 Uiso calc R 1 . .
H H25B 1.1172 0.8360 0.0129 0.078 Uiso calc R 1 . .
H H25C 1.2276 0.9122 0.0471 0.078 Uiso calc R 1 . .
C C26 1.0907(2) 1.02814(16) 0.12306(14) 0.0497(6) Uani d . 1 . .
H H26A 1.0793 1.0585 0.0811 0.075 Uiso calc R 1 . .
H H26B 1.1741 1.0469 0.1426 0.075 Uiso calc R 1 . .
H H26C 1.0348 1.0438 0.1621 0.075 Uiso calc R 1 . .
C C27 0.8389(2) 0.23513(16) 0.41999(11) 0.0395(5) Uani d . 1 . .
H H27A 0.7586 0.2034 0.4318 0.047 Uiso calc R 1 . .
H H27B 0.8909 0.2469 0.4655 0.047 Uiso calc R 1 . .
C C28 0.9290(2) 0.39283(17) 0.42381(13) 0.0520(6) Uani d . 1 . .
H H28A 0.9506 0.3906 0.4759 0.062 Uiso calc R 1 . .
H H28B 0.9053 0.4515 0.4224 0.062 Uiso calc R 1 . .
C C29 1.0401(2) 0.38505(17) 0.37607(13) 0.0514(6) Uani d . 1 . .
H H29A 1.0203 0.3921 0.3249 0.062 Uiso calc R 1 . .
H H29B 1.1069 0.4343 0.3959 0.062 Uiso calc R 1 . .
C C30 1.00556(19) 0.22506(15) 0.32323(11) 0.0373(5) Uani d . 1 . .
H H30A 1.0568 0.1817 0.3020 0.045 Uiso calc R 1 . .
H H30B 0.9758 0.2503 0.2817 0.045 Uiso calc R 1 . .
C C31 0.7064(2) 0.34530(19) 0.41613(12) 0.0513(7) Uani d . 1 . .
H H31A 0.6435 0.2977 0.3891 0.062 Uiso calc R 1 . .
H H31B 0.7018 0.4012 0.3969 0.062 Uiso calc R 1 . .
C C32 0.6758(2) 0.35875(18) 0.49879(13) 0.0475(6) Uani d . 1 . .
C C33 0.4989(2) 0.3720(2) 0.57917(12) 0.0539(7) Uani d . 1 . .
C C34 0.5486(4) 0.4646(2) 0.61952(18) 0.0978(12) Uani d . 1 . .
H H34A 0.6338 0.4684 0.6332 0.147 Uiso calc R 1 . .
H H34B 0.5028 0.4771 0.6644 0.147 Uiso calc R 1 . .
H H34C 0.5414 0.5084 0.5872 0.147 Uiso calc R 1 . .
C C35 0.5158(3) 0.2981(2) 0.62185(15) 0.0715(8) Uani d . 1 . .
H H35A 0.6011 0.3051 0.6366 0.107 Uiso calc R 1 . .
H H35B 0.4903 0.2399 0.5903 0.107 Uiso calc R 1 . .
H H35C 0.4667 0.3016 0.6662 0.107 Uiso calc R 1 . .
C C36 0.3653(3) 0.3629(3) 0.55614(16) 0.0994(14) Uani d . 1 . .
H H36A 0.3356 0.3021 0.5302 0.149 Uiso calc R 1 . .
H H36B 0.3572 0.4059 0.5232 0.149 Uiso calc R 1 . .
H H36C 0.3179 0.3749 0.6004 0.149 Uiso calc R 1 . .
C C37 1.2114(2) 0.30377(17) 0.36034(12) 0.0448(6) Uani d . 1 . .
H H37A 1.2348 0.2474 0.3696 0.054 Uiso calc R 1 . .
H H37B 1.2565 0.3527 0.3972 0.054 Uiso calc R 1 . .
C C38 1.2529(2) 0.31952(16) 0.28246(12) 0.0415(5) Uani d . 1 . .
C C39 1.4270(2) 0.30619(17) 0.19957(12) 0.0457(6) Uani d . 1 . .
C C40 1.4436(3) 0.3985(2) 0.17940(16) 0.0782(10) Uani d . 1 . .
H H40A 1.4925 0.4412 0.2182 0.117 Uiso calc R 1 . .
H H40B 1.3644 0.4157 0.1747 0.117 Uiso calc R 1 . .
H H40C 1.4846 0.3987 0.1321 0.117 Uiso calc R 1 . .
C C41 1.5463(3) 0.2778(3) 0.21366(17) 0.0913(12) Uani d . 1 . .
H H41A 1.5942 0.3227 0.2515 0.137 Uiso calc R 1 . .
H H41B 1.5909 0.2723 0.1676 0.137 Uiso calc R 1 . .
H H41C 1.5309 0.2200 0.2310 0.137 Uiso calc R 1 . .
C C42 1.3514(3) 0.23747(19) 0.14101(14) 0.0624(7) Uani d . 1 . .
H H42A 1.3902 0.2378 0.0930 0.094 Uiso calc R 1 . .
H H42B 1.2706 0.2523 0.1373 0.094 Uiso calc R 1 . .
H H42C 1.3447 0.1780 0.1549 0.094 Uiso calc R 1 . .
C C43 0.89467(19) 0.17349(15) 0.35899(11) 0.0355(5) Uani d . 1 . .
C C44 0.8031(2) 0.13555(17) 0.29429(12) 0.0441(6) Uani d . 1 . .
H H44A 0.7732 0.1856 0.2769 0.053 Uiso calc R 1 . .
H H44B 0.8447 0.1051 0.2527 0.053 Uiso calc R 1 . .
C C45 0.7287(2) 0.00207(18) 0.34212(14) 0.0500(6) Uani d . 1 . .
C C46 0.8608(2) 0.00678(16) 0.36005(14) 0.0484(6) Uani d . 1 . .
H H46A 0.8693 -0.0355 0.3944 0.058 Uiso calc R 1 . .
H H46B 0.9027 -0.0114 0.3140 0.058 Uiso calc R 1 . .
C C47 1.0343(2) 0.10550(16) 0.43226(11) 0.0383(5) Uani d . 1 . .
H H47A 1.0212 0.0744 0.4757 0.046 Uiso calc R 1 . .
H H47B 1.0644 0.1696 0.4512 0.046 Uiso calc R 1 . .
C C48 1.1329(2) 0.06838(17) 0.38605(13) 0.0428(6) Uani d . 1 . .
C C49 1.3481(2) 0.05074(17) 0.39551(13) 0.0479(6) Uani d . 1 . .
C C50 1.3835(2) 0.0824(2) 0.32272(15) 0.0701(8) Uani d . 1 . .
H H50A 1.3218 0.0539 0.2843 0.105 Uiso calc R 1 . .
H H50B 1.4616 0.0662 0.3080 0.105 Uiso calc R 1 . .
H H50C 1.3900 0.1474 0.3289 0.105 Uiso calc R 1 . .
C C51 1.4440(2) 0.0938(2) 0.45603(16) 0.0694(8) Uani d . 1 . .
H H51A 1.4203 0.0727 0.5026 0.104 Uiso calc R 1 . .
H H51B 1.4512 0.1589 0.4630 0.104 Uiso calc R 1 . .
H H51C 1.5219 0.0773 0.4413 0.104 Uiso calc R 1 . .
C C52 1.3227(3) -0.0507(2) 0.38867(19) 0.0770(9) Uani d . 1 . .
H H52A 1.2611 -0.0760 0.3495 0.116 Uiso calc R 1 . .
H H52B 1.2936 -0.0674 0.4359 0.116 Uiso calc R 1 . .
H H52C 1.3972 -0.0739 0.3763 0.116 Uiso calc 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
C5 N1 C1 . . 113.88(17) ?
C5 N1 C2 . . 115.61(18) ?
C1 N1 C2 . . 112.13(17) ?
C19 O1 C18 . . 115.68(18) ?
N1 C1 C17 . . 112.80(16) ?
N1 C1 H1A . . 109.0 ?
C17 C1 H1A . . 109.0 ?
N1 C1 H1B . . 109.0 ?
C17 C1 H1B . . 109.0 ?
H1A C1 H1B . . 107.8 ?
C11 N2 C3 . . 113.80(17) ?
C11 N2 C4 . . 113.43(16) ?
C3 N2 C4 . . 112.42(17) ?
N1 C2 C3 . . 112.03(18) ?
N1 C2 H2A . . 109.2 ?
C3 C2 H2A . . 109.2 ?
N1 C2 H2B . . 109.2 ?
C3 C2 H2B . . 109.2 ?
H2A C2 H2B . . 107.9 ?
C6 O3 C7 . . 121.86(16) ?
C21 N3 C20 . . 115.96(18) ?
C21 N3 C17 . . 120.15(17) ?
C20 N3 C17 . . 118.45(18) ?
N2 C3 C2 . . 113.11(18) ?
N2 C3 H3A . . 109.0 ?
C2 C3 H3A . . 109.0 ?
N2 C3 H3B . . 109.0 ?
C2 C3 H3B . . 109.0 ?
H3A C3 H3B . . 107.8 ?
N2 C4 C17 . . 114.40(15) ?
N2 C4 H4A . . 108.7 ?
C17 C4 H4A . . 108.7 ?
N2 C4 H4B . . 108.7 ?
C17 C4 H4B . . 108.7 ?
H4A C4 H4B . . 107.6 ?
C31 N4 C28 . . 114.8(2) ?
C31 N4 C27 . . 113.08(19) ?
C28 N4 C27 . . 112.45(18) ?
C12 O5 C13 . . 121.42(16) ?
N1 C5 C6 . . 116.49(17) ?
N1 C5 H5A . . 108.2 ?
C6 C5 H5A . . 108.2 ?
N1 C5 H5B . . 108.2 ?
C6 C5 H5B . . 108.2 ?
H5A C5 H5B . . 107.3 ?
C37 N5 C30 . . 112.76(17) ?
C37 N5 C29 . . 113.53(19) ?
C30 N5 C29 . . 112.04(18) ?
O4 C6 O3 . . 126.13(19) ?
O4 C6 C5 . . 125.0(2) ?
O3 C6 C5 . . 108.90(17) ?
C47 N6 C46 . . 115.95(17) ?
C47 N6 C43 . . 118.34(18) ?
C46 N6 C43 . . 118.06(17) ?
C22 O7 C23 . . 122.05(16) ?
O3 C7 C8 . . 110.53(19) ?
O3 C7 C10 . . 109.85(19) ?
C8 C7 C10 . . 111.7(2) ?
O3 C7 C9 . . 101.82(17) ?
C8 C7 C9 . . 111.9(2) ?
C10 C7 C9 . . 110.6(2) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C7 C9 H9A . . 109.5 ?
C7 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C7 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C45 O9 C44 . . 115.40(18) ?
C7 C10 H10A . . 109.5 ?
C7 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C7 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
N2 C11 C12 . . 116.68(17) ?
N2 C11 H11A . . 108.1 ?
C12 C11 H11A . . 108.1 ?
N2 C11 H11B . . 108.1 ?
C12 C11 H11B . . 108.1 ?
H11A C11 H11B . . 107.3 ?
C32 O11 C33 . . 122.05(18) ?
O6 C12 O5 . . 126.41(19) ?
O6 C12 C11 . . 124.6(2) ?
O5 C12 C11 . . 108.99(17) ?
O5 C13 C14 . . 109.27(18) ?
O5 C13 C15 . . 110.80(19) ?
C14 C13 C15 . . 112.8(2) ?
O5 C13 C16 . . 101.91(17) ?
C14 C13 C16 . . 110.9(2) ?
C15 C13 C16 . . 110.6(2) ?
C38 O13 C39 . . 121.81(17) ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C13 C15 H15A . . 109.5 ?
C13 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C13 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C48 O15 C49 . . 121.24(17) ?
C13 C16 H16A . . 109.5 ?
C13 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C13 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
N3 C17 C18 . . 107.69(18) ?
N3 C17 C1 . . 106.21(16) ?
C18 C17 C1 . . 109.58(17) ?
N3 C17 C4 . . 115.56(16) ?
C18 C17 C4 . . 105.89(16) ?
C1 C17 C4 . . 111.79(17) ?
O1 C18 C17 . . 112.43(18) ?
O1 C18 H18A . . 109.1 ?
C17 C18 H18A . . 109.1 ?
O1 C18 H18B . . 109.1 ?
C17 C18 H18B . . 109.1 ?
H18A C18 H18B . . 107.9 ?
O2 C19 O1 . . 119.1(2) ?
O2 C19 C20 . . 125.3(3) ?
O1 C19 C20 . . 115.6(2) ?
N3 C20 C19 . . 110.4(2) ?
N3 C20 H20A . . 109.6 ?
C19 C20 H20A . . 109.6 ?
N3 C20 H20B . . 109.6 ?
C19 C20 H20B . . 109.6 ?
H20A C20 H20B . . 108.1 ?
N3 C21 C22 . . 115.78(17) ?
N3 C21 H21A . . 108.3 ?
C22 C21 H21A . . 108.3 ?
N3 C21 H21B . . 108.3 ?
C22 C21 H21B . . 108.3 ?
H21A C21 H21B . . 107.4 ?
O8 C22 O7 . . 125.89(19) ?
O8 C22 C21 . . 124.74(18) ?
O7 C22 C21 . . 109.37(17) ?
O7 C23 C26 . . 110.53(17) ?
O7 C23 C24 . . 108.95(17) ?
C26 C23 C24 . . 112.4(2) ?
O7 C23 C25 . . 101.67(17) ?
C26 C23 C25 . . 111.9(2) ?
C24 C23 C25 . . 110.86(19) ?
C23 C24 H24A . . 109.5 ?
C23 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
C23 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
C23 C25 H25A . . 109.5 ?
C23 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
C23 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
C23 C26 H26A . . 109.5 ?
C23 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C23 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
N4 C27 C43 . . 113.62(16) ?
N4 C27 H27A . . 108.8 ?
C43 C27 H27A . . 108.8 ?
N4 C27 H27B . . 108.8 ?
C43 C27 H27B . . 108.8 ?
H27A C27 H27B . . 107.7 ?
N4 C28 C29 . . 112.69(19) ?
N4 C28 H28A . . 109.1 ?
C29 C28 H28A . . 109.1 ?
N4 C28 H28B . . 109.1 ?
C29 C28 H28B . . 109.1 ?
H28A C28 H28B . . 107.8 ?
N5 C29 C28 . . 113.17(19) ?
N5 C29 H29A . . 108.9 ?
C28 C29 H29A . . 108.9 ?
N5 C29 H29B . . 108.9 ?
C28 C29 H29B . . 108.9 ?
H29A C29 H29B . . 107.8 ?
N5 C30 C43 . . 115.51(16) ?
N5 C30 H30A . . 108.4 ?
C43 C30 H30A . . 108.4 ?
N5 C30 H30B . . 108.4 ?
C43 C30 H30B . . 108.4 ?
H30A C30 H30B . . 107.5 ?
N4 C31 C32 . . 115.91(19) ?
N4 C31 H31A . . 108.3 ?
C32 C31 H31A . . 108.3 ?
N4 C31 H31B . . 108.3 ?
C32 C31 H31B . . 108.3 ?
H31A C31 H31B . . 107.4 ?
O12 C32 O11 . . 125.8(2) ?
O12 C32 C31 . . 125.0(2) ?
O11 C32 C31 . . 109.2(2) ?
O11 C33 C34 . . 109.0(2) ?
O11 C33 C35 . . 110.2(2) ?
C34 C33 C35 . . 113.8(2) ?
O11 C33 C36 . . 101.52(19) ?
C34 C33 C36 . . 111.4(3) ?
C35 C33 C36 . . 110.3(3) ?
C33 C34 H34A . . 109.5 ?
C33 C34 H34B . . 109.5 ?
H34A C34 H34B . . 109.5 ?
C33 C34 H34C . . 109.5 ?
H34A C34 H34C . . 109.5 ?
H34B C34 H34C . . 109.5 ?
C33 C35 H35A . . 109.5 ?
C33 C35 H35B . . 109.5 ?
H35A C35 H35B . . 109.5 ?
C33 C35 H35C . . 109.5 ?
H35A C35 H35C . . 109.5 ?
H35B C35 H35C . . 109.5 ?
C33 C36 H36A . . 109.5 ?
C33 C36 H36B . . 109.5 ?
H36A C36 H36B . . 109.5 ?
C33 C36 H36C . . 109.5 ?
H36A C36 H36C . . 109.5 ?
H36B C36 H36C . . 109.5 ?
N5 C37 C38 . . 116.59(18) ?
N5 C37 H37A . . 108.1 ?
C38 C37 H37A . . 108.1 ?
N5 C37 H37B . . 108.1 ?
C38 C37 H37B . . 108.1 ?
H37A C37 H37B . . 107.3 ?
O14 C38 O13 . . 125.9(2) ?
O14 C38 C37 . . 124.3(2) ?
O13 C38 C37 . . 109.80(19) ?
C40 C39 O13 . . 110.1(2) ?
C40 C39 C42 . . 111.5(2) ?
O13 C39 C42 . . 109.13(19) ?
C40 C39 C41 . . 112.5(3) ?
O13 C39 C41 . . 102.93(18) ?
C42 C39 C41 . . 110.3(2) ?
C39 C40 H40A . . 109.5 ?
C39 C40 H40B . . 109.5 ?
H40A C40 H40B . . 109.5 ?
C39 C40 H40C . . 109.5 ?
H40A C40 H40C . . 109.5 ?
H40B C40 H40C . . 109.5 ?
C39 C41 H41A . . 109.5 ?
C39 C41 H41B . . 109.5 ?
H41A C41 H41B . . 109.5 ?
C39 C41 H41C . . 109.5 ?
H41A C41 H41C . . 109.5 ?
H41B C41 H41C . . 109.5 ?
C39 C42 H42A . . 109.5 ?
C39 C42 H42B . . 109.5 ?
H42A C42 H42B . . 109.5 ?
C39 C42 H42C . . 109.5 ?
H42A C42 H42C . . 109.5 ?
H42B C42 H42C . . 109.5 ?
N6 C43 C44 . . 107.73(18) ?
N6 C43 C27 . . 105.51(15) ?
C44 C43 C27 . . 110.47(17) ?
N6 C43 C30 . . 115.95(16) ?
C44 C43 C30 . . 104.77(16) ?
C27 C43 C30 . . 112.36(18) ?
O9 C44 C43 . . 113.18(17) ?
O9 C44 H44A . . 108.9 ?
C43 C44 H44A . . 108.9 ?
O9 C44 H44B . . 108.9 ?
C43 C44 H44B . . 108.9 ?
H44A C44 H44B . . 107.8 ?
O10 C45 O9 . . 118.8(2) ?
O10 C45 C46 . . 125.4(3) ?
O9 C45 C46 . . 115.8(2) ?
N6 C46 C45 . . 111.20(19) ?
N6 C46 H46A . . 109.4 ?
C45 C46 H46A . . 109.4 ?
N6 C46 H46B . . 109.4 ?
C45 C46 H46B . . 109.4 ?
H46A C46 H46B . . 108.0 ?
N6 C47 C48 . . 116.20(17) ?
N6 C47 H47A . . 108.2 ?
C48 C47 H47A . . 108.2 ?
N6 C47 H47B . . 108.2 ?
C48 C47 H47B . . 108.2 ?
H47A C47 H47B . . 107.4 ?
O16 C48 O15 . . 125.0(2) ?
O16 C48 C47 . . 124.9(2) ?
O15 C48 C47 . . 110.09(19) ?
O15 C49 C50 . . 111.02(18) ?
O15 C49 C52 . . 108.5(2) ?
C50 C49 C52 . . 112.9(2) ?
O15 C49 C51 . . 102.05(19) ?
C50 C49 C51 . . 110.2(2) ?
C52 C49 C51 . . 111.6(2) ?
C49 C50 H50A . . 109.5 ?
C49 C50 H50B . . 109.5 ?
H50A C50 H50B . . 109.5 ?
C49 C50 H50C . . 109.5 ?
H50A C50 H50C . . 109.5 ?
H50B C50 H50C . . 109.5 ?
C49 C51 H51A . . 109.5 ?
C49 C51 H51B . . 109.5 ?
H51A C51 H51B . . 109.5 ?
C49 C51 H51C . . 109.5 ?
H51A C51 H51C . . 109.5 ?
H51B C51 H51C . . 109.5 ?
C49 C52 H52A . . 109.5 ?
C49 C52 H52B . . 109.5 ?
H52A C52 H52B . . 109.5 ?
C49 C52 H52C . . 109.5 ?
H52A C52 H52C . . 109.5 ?
H52B C52 H52C . . 109.5 ?
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
N1 C5 . 1.442(3) ?
N1 C1 . 1.460(3) ?
N1 C2 . 1.467(3) ?
O1 C19 . 1.353(3) ?
O1 C18 . 1.439(3) ?
C1 C17 . 1.537(3) ?
C1 H1A . 0.9800 ?
C1 H1B . 0.9800 ?
N2 C11 . 1.452(3) ?
N2 C3 . 1.464(3) ?
N2 C4 . 1.463(3) ?
C2 C3 . 1.520(3) ?
C2 H2A . 0.9800 ?
C2 H2B . 0.9800 ?
O2 C19 . 1.207(3) ?
O3 C6 . 1.337(2) ?
O3 C7 . 1.484(2) ?
N3 C21 . 1.428(3) ?
N3 C20 . 1.448(3) ?
N3 C17 . 1.463(3) ?
C3 H3A . 0.9800 ?
C3 H3B . 0.9800 ?
C4 C17 . 1.540(3) ?
C4 H4A . 0.9800 ?
C4 H4B . 0.9800 ?
O4 C6 . 1.198(3) ?
N4 C31 . 1.454(3) ?
N4 C28 . 1.457(3) ?
N4 C27 . 1.462(3) ?
O5 C12 . 1.334(2) ?
O5 C13 . 1.488(2) ?
C5 C6 . 1.528(3) ?
C5 H5A . 0.9800 ?
C5 H5B . 0.9800 ?
N5 C37 . 1.452(3) ?
N5 C30 . 1.467(3) ?
N5 C29 . 1.469(3) ?
O6 C12 . 1.197(3) ?
N6 C47 . 1.444(3) ?
N6 C46 . 1.454(3) ?
N6 C43 . 1.469(3) ?
O7 C22 . 1.333(2) ?
O7 C23 . 1.492(2) ?
C7 C8 . 1.503(4) ?
C7 C10 . 1.506(4) ?
C7 C9 . 1.510(3) ?
O8 C22 . 1.206(2) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C8 H8C . 0.9700 ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C9 H9C . 0.9700 ?
O9 C45 . 1.347(3) ?
O9 C44 . 1.441(3) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C10 H10C . 0.9700 ?
O10 C45 . 1.204(3) ?
C11 C12 . 1.528(3) ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
O11 C32 . 1.330(3) ?
O11 C33 . 1.487(3) ?
O12 C32 . 1.194(3) ?
C13 C14 . 1.506(3) ?
C13 C15 . 1.509(3) ?
C13 C16 . 1.522(3) ?
O13 C38 . 1.326(3) ?
O13 C39 . 1.497(3) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C14 H14C . 0.9700 ?
O14 C38 . 1.198(3) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C15 H15C . 0.9700 ?
O15 C48 . 1.331(3) ?
O15 C49 . 1.497(3) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C16 H16C . 0.9700 ?
O16 C48 . 1.199(3) ?
C17 C18 . 1.527(3) ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C19 C20 . 1.488(3) ?
C20 H20A . 0.9800 ?
C20 H20B . 0.9800 ?
C21 C22 . 1.528(3) ?
C21 H21A . 0.9800 ?
C21 H21B . 0.9800 ?
C23 C26 . 1.503(3) ?
C23 C24 . 1.516(3) ?
C23 C25 . 1.514(3) ?
C24 H24A . 0.9700 ?
C24 H24B . 0.9700 ?
C24 H24C . 0.9700 ?
C25 H25A . 0.9700 ?
C25 H25B . 0.9700 ?
C25 H25C . 0.9700 ?
C26 H26A . 0.9700 ?
C26 H26B . 0.9700 ?
C26 H26C . 0.9700 ?
C27 C43 . 1.536(3) ?
C27 H27A . 0.9800 ?
C27 H27B . 0.9800 ?
C28 C29 . 1.520(3) ?
C28 H28A . 0.9800 ?
C28 H28B . 0.9800 ?
C29 H29A . 0.9800 ?
C29 H29B . 0.9800 ?
C30 C43 . 1.544(3) ?
C30 H30A . 0.9800 ?
C30 H30B . 0.9800 ?
C31 C32 . 1.523(3) ?
C31 H31A . 0.9800 ?
C31 H31B . 0.9800 ?
C33 C34 . 1.491(4) ?
C33 C35 . 1.503(4) ?
C33 C36 . 1.520(4) ?
C34 H34A . 0.9700 ?
C34 H34B . 0.9700 ?
C34 H34C . 0.9700 ?
C35 H35A . 0.9700 ?
C35 H35B . 0.9700 ?
C35 H35C . 0.9700 ?
C36 H36A . 0.9700 ?
C36 H36B . 0.9700 ?
C36 H36C . 0.9700 ?
C37 C38 . 1.526(3) ?
C37 H37A . 0.9800 ?
C37 H37B . 0.9800 ?
C39 C40 . 1.491(4) ?
C39 C42 . 1.503(3) ?
C39 C41 . 1.502(4) ?
C40 H40A . 0.9700 ?
C40 H40B . 0.9700 ?
C40 H40C . 0.9700 ?
C41 H41A . 0.9700 ?
C41 H41B . 0.9700 ?
C41 H41C . 0.9700 ?
C42 H42A . 0.9700 ?
C42 H42B . 0.9700 ?
C42 H42C . 0.9700 ?
C43 C44 . 1.522(3) ?
C44 H44A . 0.9800 ?
C44 H44B . 0.9800 ?
C45 C46 . 1.493(3) ?
C46 H46A . 0.9800 ?
C46 H46B . 0.9800 ?
C47 C48 . 1.514(3) ?
C47 H47A . 0.9800 ?
C47 H47B . 0.9800 ?
C49 C50 . 1.504(4) ?
C49 C52 . 1.507(4) ?
C49 C51 . 1.513(3) ?
C50 H50A . 0.9700 ?
C50 H50B . 0.9700 ?
C50 H50C . 0.9700 ?
C51 H51A . 0.9700 ?
C51 H51B . 0.9700 ?
C51 H51C . 0.9700 ?
C52 H52A . 0.9700 ?
C52 H52B . 0.9700 ?
C52 H52C . 0.9700 ?
