#------------------------------------------------------------------------------
#$Date: 2022-06-03 03:39:39 +0300 (Fri, 03 Jun 2022) $
#$Revision: 275754 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/87/7158723.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_7158723
loop_
_publ_author_name
'Xu, Wenke'
'Guo, Jiangming'
'Liu, Chang-Hong'
'Sun, Jianting'
'Lv, Min'
'Wei, Bangguo'
_publ_section_title
;
 AgNTf2 Catalyzed Cycloaddition of N-Acyliminium ions with Alkynes for the
 Synthesis of 3,4-Dihydro-1,3-oxazin-2-one Skeleton
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00900E
_journal_year                    2022
_chemical_formula_sum            'C20 H21 N O2'
_chemical_formula_weight         307.38
_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   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2022-04-26 deposited with the CCDC.	2022-06-02 downloaded from the CCDC.
;
_cell_angle_alpha                91.153(2)
_cell_angle_beta                 94.071(2)
_cell_angle_gamma                104.497(2)
_cell_formula_units_Z            4
_cell_length_a                   9.6668(6)
_cell_length_b                   13.1481(7)
_cell_length_c                   13.9023(9)
_cell_measurement_reflns_used    6924
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      48.939
_cell_measurement_theta_min      5.068
_cell_volume                     1705.09(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33470
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         2.722
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.028(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     492
_refine_ls_number_reflns         6677
_refine_ls_number_restraints     112
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0639
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0707P)²+0.4503P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1848
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3941
_reflns_number_total             6677
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00900e2.cif
_cod_data_source_block           mo_d8v21778_0m
_cod_database_code               7158723
_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   0.986
_shelx_estimated_absorpt_t_max   0.992
_shelxl_version_number           2013-4
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
O1 O 0.30087(18) 0.39556(14) 0.38925(14) 0.0851(6) Uani 1 1 d . . . . .
O2 O 0.35995(16) 0.52907(12) 0.29555(12) 0.0728(5) Uani 1 1 d . . . . .
N1 N 0.53541(19) 0.47245(15) 0.38333(14) 0.0664(5) Uani 1 1 d . . . . .
H1 H 0.5561 0.4270 0.4217 0.080 Uiso 1 1 calc R U . . .
C1 C 0.3982(3) 0.46224(19) 0.35956(18) 0.0651(6) Uani 1 1 d . . . . .
C2 C 0.6569(2) 0.55226(17) 0.35192(17) 0.0619(6) Uani 1 1 d . . . . .
H2 H 0.7067 0.5941 0.4090 0.074 Uiso 1 1 calc R U . . .
C3 C 0.6002(3) 0.62321(18) 0.28665(18) 0.0662(6) Uani 1 1 d . . . . .
H3 H 0.6654 0.6791 0.2620 0.079 Uiso 1 1 calc R U . . .
C4 C 0.4636(3) 0.61144(17) 0.26195(16) 0.0601(6) Uani 1 1 d . . . . .
C5 C 0.3961(3) 0.67731(18) 0.19870(17) 0.0650(6) Uani 1 1 d . . . . .
C6 C 0.4715(3) 0.7760(2) 0.1756(2) 0.0883(8) Uani 1 1 d . . . . .
H6 H 0.5664 0.8014 0.1997 0.106 Uiso 1 1 calc R U . . .
C7 C 0.4074(4) 0.8377(2) 0.1169(2) 0.1019(10) Uani 1 1 d . . . . .
H7 H 0.4608 0.9039 0.1019 0.122 Uiso 1 1 calc R U . . .
C8 C 0.2672(4) 0.8042(3) 0.0801(2) 0.0937(9) Uani 1 1 d D . . . .
C9 C 0.1934(3) 0.7060(3) 0.1034(2) 0.0981(9) Uani 1 1 d . . . . .
H9 H 0.0984 0.6806 0.0792 0.118 Uiso 1 1 calc R U . . .
C10 C 0.2559(3) 0.6434(2) 0.1618(2) 0.0849(8) Uani 1 1 d . . . . .
H10 H 0.2022 0.5772 0.1764 0.102 Uiso 1 1 calc R U . . .
C11 C 0.1838(11) 0.8631(8) 0.0134(7) 0.101(3) Uani 0.6 1 d D U P A 1
H11A H 0.1625 0.9203 0.0497 0.121 Uiso 0.6 1 calc R U P A 1
H11B H 0.0936 0.8157 -0.0110 0.121 Uiso 0.6 1 calc R U P A 1
C12 C 0.2709(7) 0.9071(5) -0.0716(5) 0.0975(19) Uani 0.6 1 d D U P A 1
H12A H 0.2756 0.8520 -0.1178 0.117 Uiso 0.6 1 calc R U P A 1
H12B H 0.3671 0.9471 -0.0501 0.117 Uiso 0.6 1 calc R U P A 1
C13 C 0.1629(16) 0.9899(11) -0.1198(11) 0.239(8) Uani 0.6 1 d D U P A 1
H13A H 0.1064 1.0109 -0.0717 0.287 Uiso 0.6 1 calc R U P A 1
H13B H 0.2197 1.0517 -0.1484 0.287 Uiso 0.6 1 calc R U P A 1
C14 C 0.0717(10) 0.9125(7) -0.1947(7) 0.141(3) Uani 0.6 1 d D U P A 1
H14A H 0.1315 0.8786 -0.2290 0.211 Uiso 0.6 1 calc R U P A 1
H14B H 0.0228 0.9491 -0.2393 0.211 Uiso 0.6 1 calc R U P A 1
H14C H 0.0026 0.8608 -0.1636 0.211 Uiso 0.6 1 calc R U P A 1
C11' C 0.2221(19) 0.8976(11) 0.0285(11) 0.110(6) Uani 0.4 1 d D U P A 2
H11C H 0.1365 0.9098 0.0539 0.132 Uiso 0.4 1 calc R U P A 2
H11D H 0.2984 0.9617 0.0375 0.132 Uiso 0.4 1 calc R U P A 2
C12' C 0.1942(16) 0.8637(10) -0.0760(10) 0.149(5) Uani 0.4 1 d D U P A 2
H12C H 0.0998 0.8159 -0.0872 0.179 Uiso 0.4 1 calc R U P A 2
H12D H 0.2645 0.8272 -0.0943 0.179 Uiso 0.4 1 calc R U P A 2
C13' C 0.2038(10) 0.9688(7) -0.1426(6) 0.078(2) Uani 0.4 1 d D U P A 2
H13C H 0.2547 1.0346 -0.1095 0.094 Uiso 0.4 1 calc R U P A 2
H13D H 0.2388 0.9621 -0.2055 0.094 Uiso 0.4 1 calc R U P A 2
C14' C 0.0508(16) 0.9485(17) -0.1442(17) 0.195(8) Uani 0.4 1 d D U P A 2
H14D H 0.0075 0.8984 -0.1957 0.292 Uiso 0.4 1 calc R U P A 2
H14E H 0.0227 1.0127 -0.1541 0.292 Uiso 0.4 1 calc R U P A 2
H14F H 0.0199 0.9206 -0.0838 0.292 Uiso 0.4 1 calc R U P A 2
C15 C 0.7617(2) 0.50126(17) 0.30624(19) 0.0632(6) Uani 1 1 d . . . . .
C16 C 0.7448(3) 0.4709(2) 0.2108(2) 0.0872(8) Uani 1 1 d . . . . .
H16 H 0.6679 0.4823 0.1723 0.105 Uiso 1 1 calc R U . . .
C17 C 0.8414(5) 0.4232(3) 0.1708(3) 0.1213(13) Uani 1 1 d . . . . .
H17 H 0.8289 0.4021 0.1059 0.146 Uiso 1 1 calc R U . . .
C18 C 0.9553(5) 0.4073(3) 0.2277(5) 0.1370(19) Uani 1 1 d . . . . .
H18 H 1.0206 0.3757 0.2013 0.164 Uiso 1 1 calc R U . . .
C19 C 0.9723(4) 0.4375(3) 0.3214(4) 0.1308(16) Uani 1 1 d . . . . .
H19 H 1.0496 0.4263 0.3598 0.157 Uiso 1 1 calc R U . . .
C20 C 0.8769(3) 0.4848(2) 0.3616(2) 0.0918(9) Uani 1 1 d . . . . .
H20 H 0.8905 0.5058 0.4267 0.110 Uiso 1 1 calc R U . . .
O3 O 0.42020(16) -0.31018(12) 0.48329(12) 0.0694(5) Uani 1 1 d . . . . .
O4 O 0.48503(16) -0.15323(11) 0.42249(11) 0.0663(5) Uani 1 1 d . . . . .
N2 N 0.65058(19) -0.21922(15) 0.51102(14) 0.0670(5) Uani 1 1 d . . . . .
H2A H 0.6678 -0.2700 0.5439 0.080 Uiso 1 1 calc R U . . .
C21 C 0.5171(2) -0.23224(18) 0.47477(16) 0.0586(6) Uani 1 1 d . . . . .
C22 C 0.7727(2) -0.12944(18) 0.50225(19) 0.0669(6) Uani 1 1 d . . . . .
H22 H 0.8089 -0.1003 0.5673 0.080 Uiso 1 1 calc R U . . .
C23 C 0.7215(3) -0.04779(18) 0.44804(19) 0.0714(7) Uani 1 1 d . . . . .
H23 H 0.7873 0.0157 0.4393 0.086 Uiso 1 1 calc R U . . .
C24 C 0.5889(2) -0.06007(16) 0.41169(16) 0.0595(6) Uani 1 1 d . . . . .
C25 C 0.5293(3) 0.01509(17) 0.35608(17) 0.0613(6) Uani 1 1 d . . . . .
C26 C 0.6120(3) 0.11509(19) 0.3414(2) 0.0783(7) Uani 1 1 d . . . . .
H26 H 0.7063 0.1349 0.3678 0.094 Uiso 1 1 calc R U . . .
C27 C 0.5580(3) 0.1857(2) 0.2886(2) 0.0864(8) Uani 1 1 d . . . . .
H27 H 0.6166 0.2521 0.2798 0.104 Uiso 1 1 calc R U . . .
C28 C 0.4197(4) 0.1603(2) 0.2487(2) 0.0836(8) Uani 1 1 d D . . . .
C29 C 0.3369(3) 0.0611(2) 0.2639(2) 0.0893(8) Uani 1 1 d . . . . .
H29 H 0.2424 0.0420 0.2377 0.107 Uiso 1 1 calc R U . . .
C30 C 0.3895(3) -0.0106(2) 0.3167(2) 0.0806(8) Uani 1 1 d . . . . .
H30 H 0.3303 -0.0768 0.3257 0.097 Uiso 1 1 calc R U . . .
C31 C 0.3687(15) 0.2452(11) 0.1957(8) 0.088(3) Uani 0.6 1 d D U P B 1
H31A H 0.4388 0.3120 0.2085 0.106 Uiso 0.6 1 calc R U P B 1
H31B H 0.2792 0.2515 0.2196 0.106 Uiso 0.6 1 calc R U P B 1
C32 C 0.3466(9) 0.2214(7) 0.0878(7) 0.121(3) Uani 0.6 1 d D U P B 1
H32A H 0.2510 0.1771 0.0710 0.146 Uiso 0.6 1 calc R U P B 1
H32B H 0.4157 0.1847 0.0676 0.146 Uiso 0.6 1 calc R U P B 1
C33 C 0.3693(11) 0.3422(10) 0.0302(8) 0.159(3) Uani 0.6 1 d D U P B 1
H33A H 0.3989 0.4030 0.0745 0.191 Uiso 0.6 1 calc R U P B 1
H33B H 0.4321 0.3490 -0.0220 0.191 Uiso 0.6 1 calc R U P B 1
C34 C 0.2226(10) 0.3184(10) -0.0020(9) 0.206(5) Uani 0.6 1 d D U P B 1
H34A H 0.1942 0.2489 -0.0315 0.308 Uiso 0.6 1 calc R U P B 1
H34B H 0.2068 0.3683 -0.0483 0.308 Uiso 0.6 1 calc R U P B 1
H34C H 0.1669 0.3217 0.0519 0.308 Uiso 0.6 1 calc R U P B 1
C31' C 0.343(2) 0.2271(18) 0.1825(13) 0.121(9) Uani 0.4 1 d D U P B 2
H31C H 0.2450 0.1879 0.1654 0.145 Uiso 0.4 1 calc R U P B 2
H31D H 0.3407 0.2911 0.2176 0.145 Uiso 0.4 1 calc R U P B 2
C32' C 0.4208(10) 0.2559(8) 0.0892(8) 0.085(3) Uani 0.4 1 d D U P B 2
H32C H 0.4439 0.1964 0.0576 0.103 Uiso 0.4 1 calc R U P B 2
H32D H 0.5052 0.3144 0.0989 0.103 Uiso 0.4 1 calc R U P B 2
C33' C 0.2740(15) 0.2903(8) 0.0320(9) 0.129(4) Uani 0.4 1 d D U P B 2
H33C H 0.2554 0.2647 -0.0347 0.154 Uiso 0.4 1 calc R U P B 2
H33D H 0.1881 0.2669 0.0660 0.154 Uiso 0.4 1 calc R U P B 2
C34' C 0.331(2) 0.4016(9) 0.0406(12) 0.182(6) Uani 0.4 1 d D U P B 2
H34D H 0.3323 0.4250 0.1067 0.272 Uiso 0.4 1 calc R U P B 2
H34E H 0.2713 0.4351 0.0007 0.272 Uiso 0.4 1 calc R U P B 2
H34F H 0.4262 0.4196 0.0202 0.272 Uiso 0.4 1 calc R U P B 2
C35 C 0.8917(2) -0.16611(17) 0.4568(2) 0.0655(6) Uani 1 1 d . . . . .
C36 C 0.9794(3) -0.2136(2) 0.5128(2) 0.0804(8) Uani 1 1 d . . . . .
H36 H 0.9685 -0.2194 0.5785 0.096 Uiso 1 1 calc R U . . .
C37 C 1.0837(3) -0.2528(2) 0.4724(3) 0.0955(10) Uani 1 1 d . . . . .
H37 H 1.1421 -0.2846 0.5110 0.115 Uiso 1 1 calc R U . . .
C38 C 1.1007(3) -0.2447(2) 0.3761(3) 0.1051(11) Uani 1 1 d . . . . .
H38 H 1.1704 -0.2709 0.3488 0.126 Uiso 1 1 calc R U . . .
C39 C 1.0149(4) -0.1980(3) 0.3200(3) 0.1108(11) Uani 1 1 d . . . . .
H39 H 1.0265 -0.1927 0.2543 0.133 Uiso 1 1 calc R U . . .
C40 C 0.9105(3) -0.1583(2) 0.3595(2) 0.0895(9) Uani 1 1 d . . . . .
H40 H 0.8531 -0.1264 0.3203 0.107 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 0.0033 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
C1 O2 C4 120.29(18) . . ?
C1 N1 C2 127.51(19) . . ?
C1 N1 H1 116.2 . . ?
C2 N1 H1 116.2 . . ?
O1 C1 N1 125.0(2) . . ?
O1 C1 O2 116.4(2) . . ?
N1 C1 O2 118.6(2) . . ?
N1 C2 C3 108.38(18) . . ?
N1 C2 C15 110.77(17) . . ?
C3 C2 C15 113.35(19) . . ?
N1 C2 H2 108.1 . . ?
C3 C2 H2 108.1 . . ?
C15 C2 H2 108.1 . . ?
C4 C3 C2 123.8(2) . . ?
C4 C3 H3 118.1 . . ?
C2 C3 H3 118.1 . . ?
C3 C4 O2 121.3(2) . . ?
C3 C4 C5 128.2(2) . . ?
O2 C4 C5 110.57(19) . . ?
C10 C5 C6 117.5(2) . . ?
C10 C5 C4 121.6(2) . . ?
C6 C5 C4 120.9(2) . . ?
C5 C6 C7 120.7(3) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 122.0(3) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C9 C8 C7 116.9(3) . . ?
C9 C8 C11 115.6(5) . . ?
C7 C8 C11 127.5(5) . . ?
C9 C8 C11' 133.6(7) . . ?
C7 C8 C11' 109.1(7) . . ?
C8 C9 C10 121.8(3) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C5 C10 C9 121.2(3) . . ?
C5 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C8 C11 C12 110.8(7) . . ?
C8 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 C13 99.4(7) . . ?
C11 C12 H12A 111.9 . . ?
C13 C12 H12A 111.9 . . ?
C11 C12 H12B 111.9 . . ?
C13 C12 H12B 111.9 . . ?
H12A C12 H12B 109.6 . . ?
C14 C13 C12 98.0(9) . . ?
C14 C13 H13A 112.2 . . ?
C12 C13 H13A 112.2 . . ?
C14 C13 H13B 112.2 . . ?
C12 C13 H13B 112.2 . . ?
H13A C13 H13B 109.8 . . ?
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 . . ?
C12' C11' C8 105.2(9) . . ?
C12' C11' H11C 110.7 . . ?
C8 C11' H11C 110.7 . . ?
C12' C11' H11D 110.7 . . ?
C8 C11' H11D 110.7 . . ?
H11C C11' H11D 108.8 . . ?
C11' C12' C13' 109.5(10) . . ?
C11' C12' H12C 109.8 . . ?
C13' C12' H12C 109.8 . . ?
C11' C12' H12D 109.8 . . ?
C13' C12' H12D 109.8 . . ?
H12C C12' H12D 108.2 . . ?
C14' C13' C12' 88.3(12) . . ?
C14' C13' H13C 113.9 . . ?
C12' C13' H13C 113.9 . . ?
C14' C13' H13D 113.9 . . ?
C12' C13' H13D 113.9 . . ?
H13C C13' H13D 111.1 . . ?
C13' C14' H14D 109.5 . . ?
C13' C14' H14E 109.5 . . ?
H14D C14' H14E 109.5 . . ?
C13' C14' H14F 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 109.5 . . ?
C16 C15 C20 118.8(3) . . ?
C16 C15 C2 121.6(2) . . ?
C20 C15 C2 119.6(3) . . ?
C15 C16 C17 120.6(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 119.6(4) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C19 C18 C17 119.9(4) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.8(4) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C15 C20 C19 120.3(4) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C21 O4 C24 120.78(18) . . ?
C21 N2 C22 128.12(19) . . ?
C21 N2 H2A 115.9 . . ?
C22 N2 H2A 115.9 . . ?
O3 C21 N2 125.0(2) . . ?
O3 C21 O4 117.2(2) . . ?
N2 C21 O4 117.8(2) . . ?
N2 C22 C23 108.37(19) . . ?
N2 C22 C35 109.56(19) . . ?
C23 C22 C35 114.3(2) . . ?
N2 C22 H22 108.1 . . ?
C23 C22 H22 108.1 . . ?
C35 C22 H22 108.1 . . ?
C24 C23 C22 123.9(2) . . ?
C24 C23 H23 118.1 . . ?
C22 C23 H23 118.1 . . ?
C23 C24 O4 120.9(2) . . ?
C23 C24 C25 127.7(2) . . ?
O4 C24 C25 111.39(19) . . ?
C30 C25 C26 117.3(2) . . ?
C30 C25 C24 121.7(2) . . ?
C26 C25 C24 121.0(2) . . ?
C27 C26 C25 121.6(3) . . ?
C27 C26 H26 119.2 . . ?
C25 C26 H26 119.2 . . ?
C28 C27 C26 121.3(3) . . ?
C28 C27 H27 119.4 . . ?
C26 C27 H27 119.4 . . ?
C27 C28 C29 117.2(2) . . ?
C27 C28 C31 117.1(7) . . ?
C29 C28 C31 125.6(7) . . ?
C27 C28 C31' 128.4(10) . . ?
C29 C28 C31' 114.3(10) . . ?
C28 C29 C30 122.2(3) . . ?
C28 C29 H29 118.9 . . ?
C30 C29 H29 118.9 . . ?
C25 C30 C29 120.4(3) . . ?
C25 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C28 C31 C32 111.7(8) . . ?
C28 C31 H31A 109.3 . . ?
C32 C31 H31A 109.3 . . ?
C28 C31 H31B 109.3 . . ?
C32 C31 H31B 109.3 . . ?
H31A C31 H31B 107.9 . . ?
C31 C32 C33 107.7(7) . . ?
C31 C32 H32A 110.2 . . ?
C33 C32 H32A 110.2 . . ?
C31 C32 H32B 110.2 . . ?
C33 C32 H32B 110.2 . . ?
H32A C32 H32B 108.5 . . ?
C34 C33 C32 91.5(10) . . ?
C34 C33 H33A 113.4 . . ?
C32 C33 H33A 113.4 . . ?
C34 C33 H33B 113.4 . . ?
C32 C33 H33B 113.4 . . ?
H33A C33 H33B 110.7 . . ?
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 . . ?
C32' C31' C28 111.5(12) . . ?
C32' C31' H31C 109.3 . . ?
C28 C31' H31C 109.3 . . ?
C32' C31' H31D 109.3 . . ?
C28 C31' H31D 109.3 . . ?
H31C C31' H31D 108.0 . . ?
C31' C32' C33' 92.4(9) . . ?
C31' C32' H32C 113.2 . . ?
C33' C32' H32C 113.2 . . ?
C31' C32' H32D 113.2 . . ?
C33' C32' H32D 113.2 . . ?
H32C C32' H32D 110.6 . . ?
C34' C33' C32' 97.3(12) . . ?
C34' C33' H33C 112.3 . . ?
C32' C33' H33C 112.3 . . ?
C34' C33' H33D 112.3 . . ?
C32' C33' H33D 112.3 . . ?
H33C C33' H33D 109.9 . . ?
C33' C34' H34D 109.5 . . ?
C33' C34' H34E 109.5 . . ?
H34D C34' H34E 109.5 . . ?
C33' C34' H34F 109.5 . . ?
H34D C34' H34F 109.5 . . ?
H34E C34' H34F 109.5 . . ?
C40 C35 C36 118.3(2) . . ?
C40 C35 C22 122.0(2) . . ?
C36 C35 C22 119.7(2) . . ?
C35 C36 C37 121.0(3) . . ?
C35 C36 H36 119.5 . . ?
C37 C36 H36 119.5 . . ?
C38 C37 C36 120.0(3) . . ?
C38 C37 H37 120.0 . . ?
C36 C37 H37 120.0 . . ?
C39 C38 C37 119.7(3) . . ?
C39 C38 H38 120.2 . . ?
C37 C38 H38 120.2 . . ?
C38 C39 C40 120.9(3) . . ?
C38 C39 H39 119.5 . . ?
C40 C39 H39 119.5 . . ?
C35 C40 C39 120.2(3) . . ?
C35 C40 H40 119.9 . . ?
C39 C40 H40 119.9 . . ?
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 C1 1.217(3) . ?
O2 C1 1.360(3) . ?
O2 C4 1.393(3) . ?
N1 C1 1.316(3) . ?
N1 C2 1.464(3) . ?
N1 H1 0.8600 . ?
C2 C3 1.488(3) . ?
C2 C15 1.515(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.309(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.477(3) . ?
C5 C10 1.374(4) . ?
C5 C6 1.376(3) . ?
C6 C7 1.384(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.373(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.367(4) . ?
C8 C11 1.531(8) . ?
C8 C11' 1.573(13) . ?
C9 C10 1.381(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.539(10) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.795(13) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.509(13) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C11' C12' 1.497(15) . ?
C11' H11C 0.9700 . ?
C11' H11D 0.9700 . ?
C12' C13' 1.665(13) . ?
C12' H12C 0.9700 . ?
C12' H12D 0.9700 . ?
C13' C14' 1.434(15) . ?
C13' H13C 0.9700 . ?
C13' H13D 0.9700 . ?
C14' H14D 0.9600 . ?
C14' H14E 0.9600 . ?
C14' H14F 0.9600 . ?
C15 C16 1.364(4) . ?
C15 C20 1.373(3) . ?
C16 C17 1.389(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.370(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.341(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.378(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
O3 C21 1.217(2) . ?
O4 C21 1.365(2) . ?
O4 C24 1.394(2) . ?
N2 C21 1.320(3) . ?
N2 C22 1.460(3) . ?
N2 H2A 0.8600 . ?
C22 C23 1.487(3) . ?
C22 C35 1.524(3) . ?
C22 H22 0.9800 . ?
C23 C24 1.314(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.469(3) . ?
C25 C30 1.378(3) . ?
C25 C26 1.385(3) . ?
C26 C27 1.375(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.367(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.377(4) . ?
C28 C31 1.514(8) . ?
C28 C31' 1.559(15) . ?
C29 C30 1.380(3) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 C32 1.515(12) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.766(11) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C34 1.412(11) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C31' C32' 1.552(16) . ?
C31' H31C 0.9700 . ?
C31' H31D 0.9700 . ?
C32' C33' 1.740(12) . ?
C32' H32C 0.9700 . ?
C32' H32D 0.9700 . ?
C33' C34' 1.427(14) . ?
C33' H33C 0.9700 . ?
C33' H33D 0.9700 . ?
C34' H34D 0.9600 . ?
C34' H34E 0.9600 . ?
C34' H34F 0.9600 . ?
C35 C40 1.380(4) . ?
C35 C36 1.381(3) . ?
C36 C37 1.388(4) . ?
C36 H36 0.9300 . ?
C37 C38 1.363(5) . ?
C37 H37 0.9300 . ?
C38 C39 1.362(5) . ?
C38 H38 0.9300 . ?
C39 C40 1.386(4) . ?
C39 H39 0.9300 . ?
C40 H40 0.9300 . ?
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
C2 N1 C1 O1 -178.4(2) . . . . ?
C2 N1 C1 O2 3.0(4) . . . . ?
C4 O2 C1 O1 176.4(2) . . . . ?
C4 O2 C1 N1 -4.9(3) . . . . ?
C1 N1 C2 C3 0.1(3) . . . . ?
C1 N1 C2 C15 -124.8(3) . . . . ?
N1 C2 C3 C4 -1.4(3) . . . . ?
C15 C2 C3 C4 122.0(3) . . . . ?
C2 C3 C4 O2 -0.5(4) . . . . ?
C2 C3 C4 C5 179.5(2) . . . . ?
C1 O2 C4 C3 3.8(3) . . . . ?
C1 O2 C4 C5 -176.2(2) . . . . ?
C3 C4 C5 C10 165.3(3) . . . . ?
O2 C4 C5 C10 -14.8(3) . . . . ?
C3 C4 C5 C6 -15.6(4) . . . . ?
O2 C4 C5 C6 164.4(2) . . . . ?
C10 C5 C6 C7 -0.3(4) . . . . ?
C4 C5 C6 C7 -179.5(3) . . . . ?
C5 C6 C7 C8 0.5(5) . . . . ?
C6 C7 C8 C9 -0.6(5) . . . . ?
C6 C7 C8 C11 -179.0(6) . . . . ?
C6 C7 C8 C11' 172.5(6) . . . . ?
C7 C8 C9 C10 0.5(5) . . . . ?
C11 C8 C9 C10 179.1(5) . . . . ?
C11' C8 C9 C10 -170.5(8) . . . . ?
C6 C5 C10 C9 0.3(4) . . . . ?
C4 C5 C10 C9 179.4(3) . . . . ?
C8 C9 C10 C5 -0.3(5) . . . . ?
C9 C8 C11 C12 -130.3(6) . . . . ?
C7 C8 C11 C12 48.2(10) . . . . ?
C11' C8 C11 C12 72(3) . . . . ?
C8 C11 C12 C13 -169.4(7) . . . . ?
C11 C12 C13 C14 -94.2(10) . . . . ?
C9 C8 C11' C12' -73.9(14) . . . . ?
C7 C8 C11' C12' 114.6(11) . . . . ?
C11 C8 C11' C12' -45(2) . . . . ?
C8 C11' C12' C13' -159.6(9) . . . . ?
C11' C12' C13' C14' -96.4(15) . . . . ?
N1 C2 C15 C16 85.9(3) . . . . ?
C3 C2 C15 C16 -36.1(3) . . . . ?
N1 C2 C15 C20 -94.0(3) . . . . ?
C3 C2 C15 C20 143.9(2) . . . . ?
C20 C15 C16 C17 0.7(4) . . . . ?
C2 C15 C16 C17 -179.2(2) . . . . ?
C15 C16 C17 C18 -0.5(5) . . . . ?
C16 C17 C18 C19 0.3(6) . . . . ?
C17 C18 C19 C20 -0.2(6) . . . . ?
C16 C15 C20 C19 -0.7(4) . . . . ?
C2 C15 C20 C19 179.3(3) . . . . ?
C18 C19 C20 C15 0.5(5) . . . . ?
C22 N2 C21 O3 178.6(2) . . . . ?
C22 N2 C21 O4 -0.4(4) . . . . ?
C24 O4 C21 O3 178.10(19) . . . . ?
C24 O4 C21 N2 -2.8(3) . . . . ?
C21 N2 C22 C23 3.0(3) . . . . ?
C21 N2 C22 C35 -122.3(3) . . . . ?
N2 C22 C23 C24 -2.8(4) . . . . ?
C35 C22 C23 C24 119.6(3) . . . . ?
C22 C23 C24 O4 0.2(4) . . . . ?
C22 C23 C24 C25 -179.0(2) . . . . ?
C21 O4 C24 C23 2.9(3) . . . . ?
C21 O4 C24 C25 -177.76(18) . . . . ?
C23 C24 C25 C30 175.7(3) . . . . ?
O4 C24 C25 C30 -3.5(3) . . . . ?
C23 C24 C25 C26 -4.4(4) . . . . ?
O4 C24 C25 C26 176.4(2) . . . . ?
C30 C25 C26 C27 -0.8(4) . . . . ?
C24 C25 C26 C27 179.3(2) . . . . ?
C25 C26 C27 C28 0.4(4) . . . . ?
C26 C27 C28 C29 0.1(4) . . . . ?
C26 C27 C28 C31 177.4(5) . . . . ?
C26 C27 C28 C31' -176.3(10) . . . . ?
C27 C28 C29 C30 -0.1(4) . . . . ?
C31 C28 C29 C30 -177.1(6) . . . . ?
C31' C28 C29 C30 176.7(8) . . . . ?
C26 C25 C30 C29 0.8(4) . . . . ?
C24 C25 C30 C29 -179.3(2) . . . . ?
C28 C29 C30 C25 -0.3(5) . . . . ?
C27 C28 C31 C32 110.0(10) . . . . ?
C29 C28 C31 C32 -73.0(10) . . . . ?
C31' C28 C31 C32 -46(4) . . . . ?
C28 C31 C32 C33 -153.5(8) . . . . ?
C31 C32 C33 C34 -111.8(10) . . . . ?
C27 C28 C31' C32' 58.7(19) . . . . ?
C29 C28 C31' C32' -117.8(14) . . . . ?
C31 C28 C31' C32' 86(5) . . . . ?
C28 C31' C32' C33' 163.9(15) . . . . ?
C31' C32' C33' C34' 104.5(15) . . . . ?
N2 C22 C35 C40 97.4(3) . . . . ?
C23 C22 C35 C40 -24.5(3) . . . . ?
N2 C22 C35 C36 -79.2(3) . . . . ?
C23 C22 C35 C36 158.9(2) . . . . ?
C40 C35 C36 C37 -0.1(4) . . . . ?
C22 C35 C36 C37 176.6(2) . . . . ?
C35 C36 C37 C38 0.0(4) . . . . ?
C36 C37 C38 C39 0.0(5) . . . . ?
C37 C38 C39 C40 0.1(5) . . . . ?
C36 C35 C40 C39 0.3(4) . . . . ?
C22 C35 C40 C39 -176.4(3) . . . . ?
C38 C39 C40 C35 -0.3(5) . . . . ?
