#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/43/7204332.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_7204332
loop_
_publ_author_name
'Wallfisch, Bianca C.'
'Belaj, Ferdinand'
'Wentrup, Curt'
'Kappe, C. Oliver'
'Kollenz, Gert'
_publ_section_title
;
 Synthesis and chemical reactivity of
 methoxycarbonyl-1,3-dioxinyl(pivaloyl)ketene---a persistent
 α-oxoketene
;
_journal_issue                   5
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              599
_journal_paper_doi               10.1039/b111143d
_journal_year                    2002
_chemical_formula_sum            'C28 H44 N2 O7'
_chemical_formula_weight         520.65
_chemical_melting_point          394
_chemical_name_systematic
; 
R,S-2-(1-Isopropyl-4-(isopropylimino)-2-oxo-3-pivaloylazetidin
-3-yl)-2,6-di-tert-butyl-5-methoxycarbonyl-1,3-dioxin-4(2H)-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'manual edited SHELXL-97 .cif file'
_cell_angle_alpha                90.00
_cell_angle_beta                 117.62(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.964(5)
_cell_length_b                   11.267(3)
_cell_length_c                   17.010(5)
_cell_measurement_reflns_used    71
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      18.93
_cell_measurement_theta_min      3.63
_cell_volume                     2880.7(15)
_computing_cell_refinement       'local program'
_computing_data_collection       'local program'
_computing_data_reduction        'local program'
_computing_molecular_graphics    'ORTEP (Johnson, 1965)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Stoe 4-circle'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0742
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            6210
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.70
_diffrn_standards_decay_%        3.2
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.36
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         5063
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0939
_refine_ls_R_factor_gt           0.0601
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0264P)²+1.0561P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1279
_reflns_number_gt                3621
_reflns_number_total             5063
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b111143d.txt
_cod_data_source_block           7b_A(BCW410a)
_cod_original_cell_volume        2880.7(14)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7204332
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.95786(10) 0.44116(14) 0.78707(11) 0.0205(4) Uani 1 1 d . . .
C2 C 0.91454(15) 0.5530(2) 0.75802(15) 0.0176(5) Uani 1 1 d . . .
O3 O 0.85977(10) 0.56016(15) 0.66375(10) 0.0205(4) Uani 1 1 d . . .
C4 C 0.84891(16) 0.4687(2) 0.60721(17) 0.0235(6) Uani 1 1 d . . .
O4 O 0.80247(13) 0.48645(18) 0.52917(12) 0.0388(5) Uani 1 1 d . . .
C5 C 0.89282(15) 0.3582(2) 0.64507(16) 0.0195(5) Uani 1 1 d . A .
C6 C 0.94657(15) 0.3489(2) 0.73289(16) 0.0197(6) Uani 1 1 d . A .
C21 C 0.85236(15) 0.5685(2) 0.80105(16) 0.0185(5) Uani 1 1 d . . .
C22 C 0.78241(16) 0.4700(2) 0.76644(18) 0.0272(6) Uani 1 1 d . . .
H221 H 0.7487 0.4752 0.7017 0.037(5) Uiso 1 1 calc R . .
H222 H 0.7418 0.4790 0.7923 0.037(5) Uiso 1 1 calc R . .
H223 H 0.8119 0.3926 0.7831 0.037(5) Uiso 1 1 calc R . .
C23 C 0.90392(16) 0.5579(2) 0.90215(16) 0.0231(6) Uani 1 1 d . . .
H231 H 0.8629 0.5677 0.9275 0.040(5) Uiso 1 1 calc R . .
H232 H 0.9498 0.6196 0.9255 0.040(5) Uiso 1 1 calc R . .
H233 H 0.9321 0.4796 0.9181 0.040(5) Uiso 1 1 calc R . .
C24 C 0.80499(16) 0.6885(2) 0.77689(17) 0.0226(6) Uani 1 1 d . . .
H241 H 0.7716 0.6957 0.7122 0.030(4) Uiso 1 1 calc R . .
H242 H 0.8491 0.7524 0.8005 0.030(4) Uiso 1 1 calc R . .
H243 H 0.7640 0.6944 0.8025 0.030(4) Uiso 1 1 calc R . .
C51 C 0.87688(16) 0.2634(2) 0.57827(17) 0.0228(6) Uani 1 1 d D . .
O51 O 0.92413(13) 0.24298(17) 0.54573(13) 0.0359(5) Uani 1 1 d . A .
O52 O 0.7932(3) 0.2211(6) 0.5455(6) 0.035(2) Uani 0.525(5) 1 d PD A 1
C52 C 0.7732(8) 0.1294(8) 0.4801(6) 0.038(2) Uani 0.525(5) 1 d PD A 1
H521 H 0.7734 0.1631 0.4271 0.050(12) Uiso 0.525(5) 1 calc PR A 1
H522 H 0.7144 0.0960 0.4643 0.050(12) Uiso 0.525(5) 1 calc PR A 1
H523 H 0.8182 0.0667 0.5044 0.050(12) Uiso 0.525(5) 1 calc PR A 1
O57 O 0.8113(4) 0.1879(6) 0.5689(6) 0.028(2) Uani 0.475(5) 1 d PD A 2
C57 C 0.7935(9) 0.0911(9) 0.5076(7) 0.039(3) Uani 0.475(5) 1 d PD A 2
H571 H 0.7784 0.1227 0.4486 0.055(14) Uiso 0.475(5) 1 calc PR A 2
H572 H 0.7435 0.0442 0.5046 0.055(14) Uiso 0.475(5) 1 calc PR A 2
H573 H 0.8464 0.0406 0.5279 0.055(14) Uiso 0.475(5) 1 calc PR A 2
C61 C 1.00017(16) 0.2431(2) 0.78601(18) 0.0256(6) Uani 1 1 d . . .
C62 C 0.9501(4) 0.1313(4) 0.7478(4) 0.0318(15) Uani 0.525(5) 1 d P A 1
H621 H 0.9335 0.1273 0.6845 0.042(10) Uiso 0.525(5) 1 calc PR A 1
H622 H 0.8962 0.1300 0.7554 0.042(10) Uiso 0.525(5) 1 calc PR A 1
H623 H 0.9876 0.0630 0.7785 0.042(10) Uiso 0.525(5) 1 calc PR A 1
C63 C 1.0292(4) 0.2594(5) 0.8801(3) 0.0300(15) Uani 0.525(5) 1 d P A 1
H631 H 1.0634 0.1899 0.9128 0.021(7) Uiso 0.525(5) 1 calc PR A 1
H632 H 0.9771 0.2689 0.8901 0.021(7) Uiso 0.525(5) 1 calc PR A 1
H633 H 1.0666 0.3305 0.9009 0.021(7) Uiso 0.525(5) 1 calc PR A 1
C64 C 1.0854(3) 0.2460(5) 0.7687(4) 0.0296(14) Uani 0.525(5) 1 d P A 1
H641 H 1.0663 0.2353 0.7052 0.032(8) Uiso 0.525(5) 1 calc PR A 1
H642 H 1.1263 0.1819 0.8022 0.032(8) Uiso 0.525(5) 1 calc PR A 1
H643 H 1.1157 0.3226 0.7881 0.032(8) Uiso 0.525(5) 1 calc PR A 1
C67 C 1.0040(5) 0.1353(5) 0.7369(4) 0.0389(19) Uani 0.475(5) 1 d P A 2
H671 H 1.0406 0.0745 0.7793 0.038(11) Uiso 0.475(5) 1 calc PR A 2
H672 H 1.0302 0.1561 0.6981 0.038(11) Uiso 0.475(5) 1 calc PR A 2
H673 H 0.9437 0.1045 0.7010 0.038(11) Uiso 0.475(5) 1 calc PR A 2
C68 C 0.9553(4) 0.1985(5) 0.8482(4) 0.0351(18) Uani 0.475(5) 1 d P A 2
H681 H 0.9512 0.2656 0.8827 0.046(11) Uiso 0.475(5) 1 calc PR A 2
H682 H 0.9922 0.1361 0.8885 0.046(11) Uiso 0.475(5) 1 calc PR A 2
H683 H 0.8955 0.1672 0.8103 0.046(11) Uiso 0.475(5) 1 calc PR A 2
C69 C 1.0942(4) 0.2787(5) 0.8532(4) 0.0335(17) Uani 0.475(5) 1 d P A 2
H691 H 1.0918 0.3499 0.8851 0.054(12) Uiso 0.475(5) 1 calc PR A 2
H692 H 1.1294 0.2953 0.8222 0.054(12) Uiso 0.475(5) 1 calc PR A 2
H693 H 1.1219 0.2138 0.8955 0.054(12) Uiso 0.475(5) 1 calc PR A 2
N10 N 0.99698(13) 0.7244(2) 0.66840(14) 0.0275(5) Uani 1 1 d . . .
C20 C 0.95363(16) 0.7583(2) 0.71576(16) 0.0212(6) Uani 1 1 d . . .
O20 O 0.90784(11) 0.84351(16) 0.70707(11) 0.0271(4) Uani 1 1 d . . .
C30 C 0.98881(15) 0.6474(2) 0.77776(16) 0.0192(5) Uani 1 1 d . . .
C40 C 1.03604(16) 0.6229(3) 0.72085(17) 0.0268(6) Uani 1 1 d . B .
C11 C 0.99667(18) 0.7810(3) 0.59011(18) 0.0347(7) Uani 1 1 d . . .
H11 H 1.0261 0.7257 0.5658 0.024(7) Uiso 1 1 calc R . .
C12 C 1.0487(2) 0.8946(3) 0.6155(2) 0.0394(8) Uani 1 1 d . . .
H121 H 1.1102 0.8781 0.6598 0.037(5) Uiso 1 1 calc R . .
H122 H 1.0216 0.9497 0.6406 0.037(5) Uiso 1 1 calc R . .
H123 H 1.0484 0.9303 0.5629 0.037(5) Uiso 1 1 calc R . .
C13 C 0.9013(2) 0.7991(4) 0.5195(2) 0.0677(13) Uani 1 1 d . . .
H131 H 0.8703 0.7225 0.5045 0.070(7) Uiso 1 1 calc R . .
H132 H 0.9008 0.8333 0.4663 0.070(7) Uiso 1 1 calc R . .
H133 H 0.8711 0.8531 0.5419 0.070(7) Uiso 1 1 calc R . .
C31 C 1.06009(16) 0.6583(2) 0.87607(16) 0.0214(6) Uani 1 1 d . . .
O31 O 1.09160(11) 0.56671(16) 0.91473(11) 0.0264(4) Uani 1 1 d . . .
C32 C 1.09704(18) 0.7778(2) 0.92030(17) 0.0296(6) Uani 1 1 d . . .
C33 C 1.02486(19) 0.8582(2) 0.92180(19) 0.0376(7) Uani 1 1 d . . .
H331 H 0.9787 0.8727 0.8609 0.047(5) Uiso 1 1 calc R . .
H332 H 1.0514 0.9339 0.9500 0.047(5) Uiso 1 1 calc R . .
H333 H 0.9983 0.8195 0.9554 0.047(5) Uiso 1 1 calc R . .
C34 C 1.16782(18) 0.7543(3) 1.01559(18) 0.0355(7) Uani 1 1 d . . .
H341 H 1.1928 0.8299 1.0451 0.052(6) Uiso 1 1 calc R . .
H342 H 1.2153 0.7052 1.0151 0.052(6) Uiso 1 1 calc R . .
H343 H 1.1408 0.7127 1.0477 0.052(6) Uiso 1 1 calc R . .
C35 C 1.1407(2) 0.8396(3) 0.86971(19) 0.0447(9) Uani 1 1 d . . .
H351 H 1.0958 0.8536 0.8082 0.060(6) Uiso 1 1 calc R . .
H352 H 1.1879 0.7889 0.8704 0.060(6) Uiso 1 1 calc R . .
H353 H 1.1661 0.9155 0.8983 0.060(6) Uiso 1 1 calc R . .
N40 N 1.08982(15) 0.5436(2) 0.72688(15) 0.0372(6) Uani 1 1 d D . .
C41 C 1.1223(4) 0.5164(7) 0.6600(4) 0.025(2) Uani 0.503(5) 1 d PD B 1
H41 H 1.0764 0.5428 0.6000 0.02(2) Uiso 0.503(5) 1 calc PR B 1
C42 C 1.1450(4) 0.3879(4) 0.6551(4) 0.0349(17) Uani 0.503(5) 1 d PD B 1
H421 H 1.0911 0.3394 0.6351 0.043(10) Uiso 0.503(5) 1 calc PR B 1
H422 H 1.1893 0.3611 0.7139 0.043(10) Uiso 0.503(5) 1 calc PR B 1
H423 H 1.1692 0.3798 0.6131 0.043(10) Uiso 0.503(5) 1 calc PR B 1
C43 C 1.2037(4) 0.5949(5) 0.6900(4) 0.0341(17) Uani 0.503(5) 1 d PD B 1
H431 H 1.1868 0.6778 0.6913 0.032(10) Uiso 0.503(5) 1 calc PR B 1
H432 H 1.2287 0.5867 0.6486 0.032(10) Uiso 0.503(5) 1 calc PR B 1
H433 H 1.2483 0.5709 0.7496 0.032(10) Uiso 0.503(5) 1 calc PR B 1
C46 C 1.1349(5) 0.5665(6) 0.6701(5) 0.030(2) Uani 0.497(5) 1 d PD B 2
H46 H 1.1372 0.6530 0.6583 0.018(13) Uiso 0.497(5) 1 calc PR B 2
C47 C 1.0765(4) 0.4988(7) 0.5868(4) 0.0396(19) Uani 0.497(5) 1 d PD B 2
H471 H 1.0182 0.5376 0.5564 0.042(10) Uiso 0.497(5) 1 calc PR B 2
H472 H 1.0688 0.4173 0.6022 0.042(10) Uiso 0.497(5) 1 calc PR B 2
H473 H 1.1043 0.4975 0.5476 0.042(10) Uiso 0.497(5) 1 calc PR B 2
C48 C 1.2269(4) 0.5126(7) 0.7191(5) 0.055(2) Uani 0.497(5) 1 d PD B 2
H481 H 1.2633 0.5605 0.7716 0.046(11) Uiso 0.497(5) 1 calc PR B 2
H482 H 1.2548 0.5107 0.6799 0.046(11) Uiso 0.497(5) 1 calc PR B 2
H483 H 1.2222 0.4315 0.7374 0.046(11) Uiso 0.497(5) 1 calc PR B 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 C2 124.01(18) . . yes
O1 C2 O3 113.56(19) . . yes
O1 C2 C21 106.90(19) . . ?
O3 C2 C21 106.98(18) . . ?
O1 C2 C30 107.01(18) . . yes
O3 C2 C30 103.97(18) . . yes
C21 C2 C30 118.7(2) . . ?
C4 O3 C2 123.49(19) . . yes
O4 C4 O3 117.2(2) . . yes
O4 C4 C5 125.0(2) . . yes
O3 C4 C5 117.7(2) . . yes
C6 C5 C4 120.5(2) . . yes
C4 C5 C51 113.9(2) . . yes
C6 C5 C51 125.5(2) . . yes
O1 C6 C5 120.6(2) . . yes
O1 C6 C61 110.1(2) . . yes
C5 C6 C61 129.2(2) . . yes
C24 C21 C22 108.74(19) . . ?
C24 C21 C23 109.1(2) . . ?
C22 C21 C23 108.3(2) . . ?
C24 C21 C2 111.2(2) . . ?
C22 C21 C2 108.3(2) . . ?
C23 C21 C2 111.28(19) . . ?
C21 C22 H221 109.5 . . ?
C21 C22 H222 109.5 . . ?
H221 C22 H222 109.5 . . ?
C21 C22 H223 109.5 . . ?
H221 C22 H223 109.5 . . ?
H222 C22 H223 109.5 . . ?
C21 C23 H231 109.5 . . ?
C21 C23 H232 109.5 . . ?
H231 C23 H232 109.5 . . ?
C21 C23 H233 109.5 . . ?
H231 C23 H233 109.5 . . ?
H232 C23 H233 109.5 . . ?
C21 C24 H241 109.5 . . ?
C21 C24 H242 109.5 . . ?
H241 C24 H242 109.5 . . ?
C21 C24 H243 109.5 . . ?
H241 C24 H243 109.5 . . ?
H242 C24 H243 109.5 . . ?
O51 C51 O52 123.1(5) . . ?
O51 C51 O57 121.3(5) . . ?
O52 C51 O57 22.6(5) . . ?
O51 C51 C5 124.8(2) . . ?
O52 C51 C5 110.6(4) . . ?
O57 C51 C5 113.0(4) . . ?
C51 O52 C52 113.5(8) . . ?
C51 O57 C57 116.7(9) . . ?
O57 C57 H571 109.5 . . ?
O57 C57 H572 109.5 . . ?
H571 C57 H572 109.5 . . ?
O57 C57 H573 109.5 . . ?
H571 C57 H573 109.5 . . ?
H572 C57 H573 109.5 . . ?
C63 C61 C62 114.9(4) . . ?
C63 C61 C67 129.8(4) . . ?
C62 C61 C67 39.8(3) . . ?
C63 C61 C6 111.1(3) . . ?
C62 C61 C6 110.0(3) . . ?
C67 C61 C6 118.4(3) . . ?
C63 C61 C69 55.8(3) . . ?
C62 C61 C69 137.5(4) . . ?
C67 C61 C69 109.4(4) . . ?
C6 C61 C69 111.7(3) . . ?
C63 C61 C64 109.0(3) . . ?
C62 C61 C64 108.5(3) . . ?
C67 C61 C64 68.7(4) . . ?
C6 C61 C64 102.5(3) . . ?
C69 C61 C64 54.1(3) . . ?
C63 C61 C68 49.5(3) . . ?
C62 C61 C68 71.4(3) . . ?
C67 C61 C68 105.4(4) . . ?
C6 C61 C68 107.2(3) . . ?
C69 C61 C68 103.6(4) . . ?
C64 C61 C68 148.3(3) . . ?
C61 C62 H621 109.5 . . ?
C61 C62 H622 109.5 . . ?
H621 C62 H622 109.5 . . ?
C61 C62 H623 109.5 . . ?
H621 C62 H623 109.5 . . ?
H622 C62 H623 109.5 . . ?
C61 C63 H631 109.5 . . ?
C61 C63 H632 109.5 . . ?
H631 C63 H632 109.5 . . ?
C61 C63 H633 109.5 . . ?
H631 C63 H633 109.5 . . ?
H632 C63 H633 109.5 . . ?
C61 C64 H641 109.5 . . ?
C61 C64 H642 109.5 . . ?
H641 C64 H642 109.5 . . ?
C61 C64 H643 109.5 . . ?
H641 C64 H643 109.5 . . ?
H642 C64 H643 109.5 . . ?
C61 C67 H671 109.5 . . ?
C61 C67 H672 109.5 . . ?
H671 C67 H672 109.5 . . ?
C61 C67 H673 109.5 . . ?
H671 C67 H673 109.5 . . ?
H672 C67 H673 109.5 . . ?
C61 C68 H681 109.5 . . ?
C61 C68 H682 109.5 . . ?
H681 C68 H682 109.5 . . ?
C61 C68 H683 109.5 . . ?
H681 C68 H683 109.5 . . ?
H682 C68 H683 109.5 . . ?
C61 C69 H691 109.5 . . ?
C61 C69 H692 109.5 . . ?
H691 C69 H692 109.5 . . ?
C61 C69 H693 109.5 . . ?
H691 C69 H693 109.5 . . ?
H692 C69 H693 109.5 . . ?
C20 N10 C40 94.4(2) . . yes
C20 N10 C11 129.1(2) . . yes
C40 N10 C11 136.5(2) . . yes
O20 C20 N10 130.0(2) . . yes
O20 C20 C30 138.2(2) . . yes
N10 C20 C30 91.9(2) . . yes
C40 C30 C31 108.62(19) . . ?
C40 C30 C2 110.2(2) . . ?
C31 C30 C2 115.7(2) . . ?
C20 C30 C40 82.34(18) . . yes
C31 C30 C20 121.9(2) . . ?
C2 C30 C20 112.44(19) . . ?
N40 C40 N10 138.0(2) . . yes
N40 C40 C30 130.6(2) . . yes
N10 C40 C30 91.3(2) . . yes
N10 C11 C12 110.7(2) . . ?
N10 C11 C13 109.2(2) . . ?
C12 C11 C13 112.5(3) . . ?
N10 C11 H11 108.1 . . ?
C12 C11 H11 108.1 . . ?
C13 C11 H11 108.1 . . ?
C11 C12 H121 109.5 . . ?
C11 C12 H122 109.5 . . ?
H121 C12 H122 109.5 . . ?
C11 C12 H123 109.5 . . ?
H121 C12 H123 109.5 . . ?
H122 C12 H123 109.5 . . ?
C11 C13 H131 109.5 . . ?
C11 C13 H132 109.5 . . ?
H131 C13 H132 109.5 . . ?
C11 C13 H133 109.5 . . ?
H131 C13 H133 109.5 . . ?
H132 C13 H133 109.5 . . ?
O31 C31 C32 120.5(2) . . ?
O31 C31 C30 116.6(2) . . ?
C32 C31 C30 122.6(2) . . ?
C31 C32 C34 108.1(2) . . ?
C31 C32 C33 112.4(2) . . ?
C34 C32 C33 109.0(2) . . ?
C31 C32 C35 108.5(2) . . ?
C34 C32 C35 109.1(2) . . ?
C33 C32 C35 109.7(2) . . ?
C32 C33 H331 109.5 . . ?
C32 C33 H332 109.5 . . ?
H331 C33 H332 109.5 . . ?
C32 C33 H333 109.5 . . ?
H331 C33 H333 109.5 . . ?
H332 C33 H333 109.5 . . ?
C32 C34 H341 109.5 . . ?
C32 C34 H342 109.5 . . ?
H341 C34 H342 109.5 . . ?
C32 C34 H343 109.5 . . ?
H341 C34 H343 109.5 . . ?
H342 C34 H343 109.5 . . ?
C32 C35 H351 109.5 . . ?
C32 C35 H352 109.5 . . ?
H351 C35 H352 109.5 . . ?
C32 C35 H353 109.5 . . ?
H351 C35 H353 109.5 . . ?
H352 C35 H353 109.5 . . ?
C40 N40 C46 113.2(3) . . ?
C40 N40 C41 126.4(4) . . yes
C46 N40 C41 23.0(3) . . ?
N40 C41 C42 115.4(6) . . ?
N40 C41 C43 102.8(4) . . ?
C42 C41 C43 111.2(5) . . ?
N40 C41 H41 109.0 . . ?
C42 C41 H41 109.0 . . ?
C43 C41 H41 109.0 . . ?
C41 C42 H421 109.5 . . ?
C41 C42 H422 109.5 . . ?
H421 C42 H422 109.5 . . ?
C41 C42 H423 109.5 . . ?
H421 C42 H423 109.5 . . ?
H422 C42 H423 109.5 . . ?
C41 C43 H431 109.5 . . ?
C41 C43 H432 109.5 . . ?
H431 C43 H432 109.5 . . ?
C41 C43 H433 109.5 . . ?
H431 C43 H433 109.5 . . ?
H432 C43 H433 109.5 . . ?
N40 C46 C47 102.0(5) . . ?
N40 C46 C48 106.2(5) . . ?
C47 C46 C48 112.0(5) . . ?
N40 C46 H46 112.0 . . ?
C47 C46 H46 112.0 . . ?
C48 C46 H46 112.0 . . ?
C46 C47 H471 109.5 . . ?
C46 C47 H472 109.5 . . ?
H471 C47 H472 109.5 . . ?
C46 C47 H473 109.5 . . ?
H471 C47 H473 109.5 . . ?
H472 C47 H473 109.5 . . ?
C46 C48 H481 109.5 . . ?
C46 C48 H482 109.5 . . ?
H481 C48 H482 109.5 . . ?
C46 C48 H483 109.5 . . ?
H481 C48 H483 109.5 . . ?
H482 C48 H483 109.5 . . ?
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
O1 C6 1.343(3) . yes
O1 C2 1.426(3) . yes
C2 O3 1.435(3) . yes
C2 C21 1.548(3) . ?
C2 C30 1.562(3) . yes
O3 C4 1.362(3) . yes
C4 O4 1.205(3) . yes
C4 C5 1.441(3) . yes
C5 C6 1.346(3) . yes
C5 C51 1.490(3) . ?
C6 C61 1.517(3) . ?
C21 C24 1.529(3) . ?
C21 C22 1.529(3) . ?
C21 C23 1.530(3) . ?
C22 H221 0.9800 . ?
C22 H222 0.9800 . ?
C22 H223 0.9800 . ?
C23 H231 0.9800 . ?
C23 H232 0.9800 . ?
C23 H233 0.9800 . ?
C24 H241 0.9800 . ?
C24 H242 0.9800 . ?
C24 H243 0.9800 . ?
C51 O51 1.189(3) . ?
C51 O52 1.349(4) . ?
C51 O57 1.350(4) . ?
O52 C52 1.439(5) . ?
C52 H521 0.9800 . ?
C52 H522 0.9800 . ?
C52 H523 0.9800 . ?
O57 C57 1.440(5) . ?
C57 H571 0.9800 . ?
C57 H572 0.9800 . ?
C57 H573 0.9800 . ?
C61 C63 1.451(6) . ?
C61 C62 1.489(6) . ?
C61 C67 1.493(6) . ?
C61 C69 1.524(6) . ?
C61 C64 1.604(5) . ?
C61 C68 1.642(6) . ?
C62 H621 0.9800 . ?
C62 H622 0.9800 . ?
C62 H623 0.9800 . ?
C63 H631 0.9800 . ?
C63 H632 0.9800 . ?
C63 H633 0.9800 . ?
C64 H641 0.9800 . ?
C64 H642 0.9800 . ?
C64 H643 0.9800 . ?
C67 H671 0.9800 . ?
C67 H672 0.9800 . ?
C67 H673 0.9800 . ?
C68 H681 0.9800 . ?
C68 H682 0.9800 . ?
C68 H683 0.9800 . ?
C69 H691 0.9800 . ?
C69 H692 0.9800 . ?
C69 H693 0.9800 . ?
N10 C20 1.373(3) . yes
N10 C40 1.412(3) . yes
N10 C11 1.474(3) . yes
C20 O20 1.200(3) . yes
C20 C30 1.564(3) . yes
C30 C31 1.549(3) . yes
C30 C40 1.541(3) . yes
C40 N40 1.247(3) . yes
C11 C12 1.501(4) . ?
C11 C13 1.517(4) . ?
C11 H11 1.0000 . ?
C12 H121 0.9800 . ?
C12 H122 0.9800 . ?
C12 H123 0.9800 . ?
C13 H131 0.9800 . ?
C13 H132 0.9800 . ?
C13 H133 0.9800 . ?
C31 O31 1.207(3) . yes
C31 C32 1.528(4) . ?
C32 C34 1.528(4) . ?
C32 C33 1.533(4) . ?
C32 C35 1.538(4) . ?
C33 H331 0.9800 . ?
C33 H332 0.9800 . ?
C33 H333 0.9800 . ?
C34 H341 0.9800 . ?
C34 H342 0.9800 . ?
C34 H343 0.9800 . ?
C35 H351 0.9800 . ?
C35 H352 0.9800 . ?
C35 H353 0.9800 . ?
N40 C46 1.506(5) . ?
N40 C41 1.507(5) . yes
C41 C42 1.511(9) . ?
C41 C43 1.516(6) . ?
C41 H41 1.0000 . ?
C42 H421 0.9800 . ?
C42 H422 0.9800 . ?
C42 H423 0.9800 . ?
C43 H431 0.9800 . ?
C43 H432 0.9800 . ?
C43 H433 0.9800 . ?
C46 C47 1.506(9) . ?
C46 C48 1.515(6) . ?
C46 H46 1.0000 . ?
C47 H471 0.9800 . ?
C47 H472 0.9800 . ?
C47 H473 0.9800 . ?
C48 H481 0.9800 . ?
C48 H482 0.9800 . ?
C48 H483 0.9800 . ?
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
C6 O1 C2 O3 -2.5(3) . . . . yes
O1 C2 O3 C4 0.9(3) . . . . yes
C2 O3 C4 C5 2.0(3) . . . . yes
O3 C4 C5 C6 -3.7(3) . . . . yes
C4 C5 C6 O1 2.2(4) . . . . yes
C5 C6 O1 C2 1.0(3) . . . . yes
C6 O1 C2 C21 115.2(2) . . . . ?
C6 O1 C2 C30 -116.6(2) . . . . ?
C21 C2 O3 C4 -116.8(2) . . . . ?
C30 C2 O3 C4 116.8(2) . . . . ?
C2 O3 C4 O4 -178.6(2) . . . . yes
O4 C4 C5 C6 177.0(3) . . . . ?
O4 C4 C5 C51 0.5(4) . . . . ?
O3 C4 C5 C51 179.8(2) . . . . yes
C2 O1 C6 C61 -178.20(19) . . . . ?
C51 C5 C6 O1 178.3(2) . . . . ?
C4 C5 C6 C61 -178.7(2) . . . . ?
C51 C5 C6 C61 -2.7(4) . . . . ?
O1 C2 C21 C24 177.83(18) . . . . ?
O3 C2 C21 C24 -60.2(2) . . . . ?
C30 C2 C21 C24 56.8(3) . . . . ?
O1 C2 C21 C22 -62.8(2) . . . . ?
O3 C2 C21 C22 59.2(2) . . . . ?
C30 C2 C21 C22 176.2(2) . . . . ?
O1 C2 C21 C23 56.1(2) . . . . ?
O3 C2 C21 C23 178.0(2) . . . . ?
C30 C2 C21 C23 -64.9(3) . . . . ?
C6 C5 C51 O51 -82.6(4) . . . . ?
C4 C5 C51 O51 93.7(3) . . . . yes
C6 C5 C51 O52 110.6(4) . . . . ?
C4 C5 C51 O52 -73.1(4) . . . . ?
C6 C5 C51 O57 86.4(5) . . . . ?
C4 C5 C51 O57 -97.3(4) . . . . ?
O51 C51 O52 C52 12.7(8) . . . . ?
O57 C51 O52 C52 -80(2) . . . . ?
C5 C51 O52 C52 179.7(5) . . . . ?
O51 C51 O57 C57 -8.6(9) . . . . ?
O52 C51 O57 C57 93(2) . . . . ?
C5 C51 O57 C57 -178.0(6) . . . . ?
O1 C6 C61 C63 14.9(4) . . . . ?
C5 C6 C61 C63 -164.2(3) . . . . ?
O1 C6 C61 C62 143.3(3) . . . . ?
C5 C6 C61 C62 -35.8(4) . . . . ?
O1 C6 C61 C67 -173.8(4) . . . . ?
C5 C6 C61 C67 7.1(5) . . . . ?
O1 C6 C61 C69 -45.4(4) . . . . ?
C5 C6 C61 C69 135.5(4) . . . . ?
O1 C6 C61 C64 -101.4(3) . . . . ?
C5 C6 C61 C64 79.5(4) . . . . ?
O1 C6 C61 C68 67.4(3) . . . . ?
C5 C6 C61 C68 -111.7(4) . . . . ?
C40 N10 C20 O20 177.9(3) . . . . ?
C11 N10 C20 O20 -2.9(5) . . . . yes
C40 N10 C20 C30 -1.9(2) . . . . ?
C11 N10 C20 C30 177.4(3) . . . . ?
O1 C2 C30 C40 65.2(2) . . . . ?
O3 C2 C30 C40 -55.2(2) . . . . ?
C21 C2 C30 C40 -173.9(2) . . . . yes
O1 C2 C30 C31 -58.5(3) . . . . yes
O3 C2 C30 C31 -178.94(19) . . . . yes
C21 C2 C30 C31 62.4(3) . . . . ?
O1 C2 C30 C20 155.11(18) . . . . yes
O3 C2 C30 C20 34.7(2) . . . . yes
C21 C2 C30 C20 -84.0(3) . . . . ?
O20 C20 C30 C40 -178.0(3) . . . . yes
N10 C20 C30 C40 1.76(18) . . . . yes
O20 C20 C30 C31 -70.8(4) . . . . ?
N10 C20 C30 C31 109.0(2) . . . . ?
O20 C20 C30 C2 73.3(4) . . . . ?
N10 C20 C30 C2 -107.0(2) . . . . ?
C20 N10 C40 N40 -175.3(4) . . . . ?
C11 N10 C40 N40 5.5(6) . . . . yes
C20 N10 C40 C30 1.9(2) . . . . ?
C11 N10 C40 C30 -177.3(3) . . . . ?
C31 C30 C40 N40 54.8(4) . . . . ?
C2 C30 C40 N40 -73.0(4) . . . . ?
C20 C30 C40 N40 175.9(3) . . . . ?
C31 C30 C40 N10 -122.8(2) . . . . ?
C2 C30 C40 N10 109.4(2) . . . . ?
C20 C30 C40 N10 -1.71(18) . . . . ?
C20 N10 C11 C12 71.9(3) . . . . ?
C40 N10 C11 C12 -109.2(3) . . . . ?
C20 N10 C11 C13 -52.5(4) . . . . ?
C40 N10 C11 C13 126.4(3) . . . . ?
C40 C30 C31 O31 -77.6(3) . . . . ?
C2 C30 C31 O31 46.9(3) . . . . ?
C20 C30 C31 O31 -170.1(2) . . . . ?
C40 C30 C31 C32 95.9(3) . . . . ?
C2 C30 C31 C32 -139.6(2) . . . . ?
C20 C30 C31 C32 3.3(3) . . . . ?
O31 C31 C32 C34 -4.8(3) . . . . ?
C30 C31 C32 C34 -178.0(2) . . . . ?
O31 C31 C32 C33 -125.1(3) . . . . ?
C30 C31 C32 C33 61.7(3) . . . . ?
O31 C31 C32 C35 113.4(3) . . . . ?
C30 C31 C32 C35 -59.8(3) . . . . ?
N10 C40 N40 C46 8.6(6) . . . . ?
C30 C40 N40 C46 -167.8(4) . . . . ?
N10 C40 N40 C41 -13.2(6) . . . . yes
C30 C40 N40 C41 170.5(4) . . . . ?
C40 N40 C41 C42 -149.0(4) . . . . ?
C46 N40 C41 C42 149.9(15) . . . . ?
C40 N40 C41 C43 89.7(6) . . . . ?
C46 N40 C41 C43 28.7(9) . . . . ?
C40 N40 C46 C47 -94.2(5) . . . . ?
C41 N40 C46 C47 35.8(12) . . . . ?
C40 N40 C46 C48 148.3(5) . . . . ?
C41 N40 C46 C48 -81.7(11) . . . . ?
