#------------------------------------------------------------------------------
#$Date: 2022-05-05 23:56:28 +0300 (Thu, 05 May 2022) $
#$Revision: 275072 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/41/7244110.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_7244110
loop_
_publ_author_name
'Galeev, Andrew R.'
'Moroz, Anna A.'
'Dmitriev, Maksim V.'
'Maslivets, Andrey N.'
_publ_section_title
;
 Cycloaddition of Huisgen 1,4-dipoles: synthesis and rapid epimerization
 of functionalized spiropyrido[2,1-b][1,3]oxazine-pyrroles and
 related products.
;
_journal_issue                   1
_journal_name_full               'RSC advances'
_journal_page_first              578
_journal_page_last               587
_journal_paper_doi               10.1039/d1ra08384h
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety         'C31 H28 N2 O8'
_chemical_formula_sum            'C31 H28 N2 O8'
_chemical_formula_weight         556.55
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2021-09-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-10-31 deposited with the CCDC.	2021-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                95.263(12)
_cell_angle_beta                 107.966(12)
_cell_angle_gamma                103.507(13)
_cell_formula_units_Z            2
_cell_length_a                   11.1868(16)
_cell_length_b                   11.4255(18)
_cell_length_c                   12.2739(16)
_cell_measurement_reflns_used    3391
_cell_measurement_temperature    295.15
_cell_measurement_theta_max      29.0220
_cell_measurement_theta_min      3.7530
_cell_volume                     1428.1(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      295.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4752
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.840
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -5.00   64.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       14.3197   77.0000  -30.0000 69

#__ type_ start__ end____ width___ exp.time_
  2 omega  -17.00   80.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       14.3197   38.0000  150.0000 97

#__ type_ start__ end____ width___ exp.time_
  3 omega  -67.00   50.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       14.3197  -77.0000 -150.0000 117

#__ type_ start__ end____ width___ exp.time_
  4 omega -106.00  -80.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8666  178.0000    0.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Ruby'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0567817000
_diffrn_orient_matrix_UB_12      0.0413830000
_diffrn_orient_matrix_UB_13      0.0416047000
_diffrn_orient_matrix_UB_21      -0.0243536000
_diffrn_orient_matrix_UB_22      -0.0158858000
_diffrn_orient_matrix_UB_23      0.0451716000
_diffrn_orient_matrix_UB_31      0.0315172000
_diffrn_orient_matrix_UB_32      -0.0473648000
_diffrn_orient_matrix_UB_33      0.0062304000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.840
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10695
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.359
_diffrn_reflns_theta_min         3.425
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         6592
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0592
_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)+(0.0865P)²+0.1786P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1542
_refine_ls_wR_factor_ref         0.1804
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4505
_reflns_number_total             6592
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra08384h2.cif
_cod_data_source_block           psu-486(aa-36)
_cod_depositor_comments
'Adding full bibliography for 7244108--7244111.cif.'
_cod_database_code               7244110
_shelx_shelxl_version_number     2018/3
_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_max   0.963
_shelx_estimated_absorpt_t_min   0.946
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C17(H17), C18(H18),
 C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C16(H16B,H16C,H16A), C27(H27A,H27B,H27C), C29(H29A,H29B,H29C), C31(H31A,H31B,
 H31C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
C1 C 0.59852(17) 0.74551(16) 0.41307(15) 0.0333(4) Uani 1 1 d . . . . .
N1 N 0.72322(14) 0.73358(14) 0.46142(13) 0.0366(4) Uani 1 1 d . . . . .
O1 O 0.51002(12) 0.71689(12) 0.45030(11) 0.0407(3) Uani 1 1 d . . . . .
C2 C 0.59609(16) 0.81023(16) 0.30804(15) 0.0325(4) Uani 1 1 d . . . . .
N2 N 0.40431(14) 0.90953(13) 0.17024(12) 0.0342(4) Uani 1 1 d . . . . .
O2 O 0.70476(17) 0.9122(2) 0.13816(16) 0.0880(7) Uani 1 1 d . . . . .
C3 C 0.73221(17) 0.82269(16) 0.30483(16) 0.0362(4) Uani 1 1 d . . . . .
O3 O 0.88891(17) 0.8658(2) 0.21717(18) 0.0900(7) Uani 1 1 d . . . . .
C4 C 0.80009(17) 0.77616(16) 0.39357(16) 0.0355(4) Uani 1 1 d . . . . .
O4 O 0.58523(12) 0.93031(11) 0.33843(11) 0.0388(3) Uani 1 1 d . . . . .
C5 C 0.48813(16) 0.73959(16) 0.19606(15) 0.0331(4) Uani 1 1 d . . . . .
O5 O 0.55544(16) 0.56156(13) 0.22918(14) 0.0601(4) Uani 1 1 d . . . . .
C6 C 0.41120(16) 0.79757(16) 0.12564(15) 0.0330(4) Uani 1 1 d . . . . .
O6 O 0.37825(14) 0.54838(12) 0.07567(13) 0.0537(4) Uani 1 1 d . . . . .
C7 C 0.37871(19) 0.99847(18) 0.10416(18) 0.0433(5) Uani 1 1 d . . . . .
H7 H 0.359864 0.981519 0.024139 0.052 Uiso 1 1 calc R U . . .
O7 O 0.20445(14) 0.72976(17) -0.02459(14) 0.0671(5) Uani 1 1 d . . . . .
C8 C 0.3807(2) 1.1076(2) 0.1534(2) 0.0565(6) Uani 1 1 d . . . . .
H8 H 0.360680 1.165443 0.107487 0.068 Uiso 1 1 calc R U . . .
O8 O 0.38351(14) 0.73084(16) -0.06908(12) 0.0579(4) Uani 1 1 d . . . . .
C9 C 0.4137(2) 1.1368(2) 0.2776(2) 0.0551(6) Uani 1 1 d . . . . .
H9 H 0.411968 1.212596 0.310947 0.066 Uiso 1 1 calc R U . . .
C10 C 0.4465(2) 1.05711(18) 0.34487(18) 0.0478(5) Uani 1 1 d . . . . .
H10 H 0.467156 1.078467 0.424778 0.057 Uiso 1 1 calc R U . . .
C11 C 0.45146(17) 0.93534(16) 0.29739(15) 0.0345(4) Uani 1 1 d . . . . .
H11 H 0.398443 0.872530 0.325626 0.041 Uiso 1 1 calc R U . . .
C12 C 0.76579(17) 0.68496(16) 0.56565(15) 0.0350(4) Uani 1 1 d . . . . .
C13 C 0.69767(18) 0.57063(17) 0.57308(17) 0.0408(4) Uani 1 1 d . . . . .
H13 H 0.623098 0.525940 0.511885 0.049 Uiso 1 1 calc R U . . .
C14 C 0.7417(2) 0.5234(2) 0.6727(2) 0.0505(5) Uani 1 1 d . . . . .
H14 H 0.695043 0.446582 0.678004 0.061 Uiso 1 1 calc R U . . .
C15 C 0.8533(2) 0.5866(2) 0.7650(2) 0.0554(6) Uani 1 1 d . . . . .
C16 C 0.9075(3) 0.5285(3) 0.8680(3) 0.0894(10) Uani 1 1 d . . . . .
H16B H 0.931199 0.585724 0.938569 0.134 Uiso 1 1 calc R U . . .
H16C H 0.983325 0.506005 0.862966 0.134 Uiso 1 1 calc R U . . .
H16A H 0.842337 0.456895 0.867885 0.134 Uiso 1 1 calc R U . . .
C17 C 0.9177(2) 0.7015(2) 0.75613(19) 0.0571(6) Uani 1 1 d . . . . .
H17 H 0.992151 0.746404 0.817391 0.069 Uiso 1 1 calc R U . . .
C18 C 0.8745(2) 0.75169(19) 0.65832(18) 0.0496(5) Uani 1 1 d . . . . .
H18 H 0.918408 0.830330 0.654755 0.060 Uiso 1 1 calc R U . . .
C19 C 0.93139(17) 0.75632(17) 0.42201(17) 0.0387(4) Uani 1 1 d . . . . .
C20 C 0.9417(2) 0.6401(2) 0.4041(2) 0.0627(7) Uani 1 1 d . . . . .
H20 H 0.866354 0.574997 0.374611 0.075 Uiso 1 1 calc R U . . .
C21 C 1.0619(3) 0.6179(3) 0.4290(3) 0.0868(10) Uani 1 1 d . . . . .
H21 H 1.067112 0.538150 0.415384 0.104 Uiso 1 1 calc R U . . .
C22 C 1.1735(3) 0.7116(3) 0.4732(3) 0.0782(8) Uani 1 1 d . . . . .
H22 H 1.254675 0.696218 0.489844 0.094 Uiso 1 1 calc R U . . .
C23 C 1.1653(2) 0.8255(3) 0.4926(3) 0.0954(11) Uani 1 1 d . . . . .
H23 H 1.241222 0.889691 0.524766 0.114 Uiso 1 1 calc R U . . .
C24 C 1.0443(2) 0.8490(2) 0.4652(3) 0.0847(10) Uani 1 1 d . . . . .
H24 H 1.040187 0.929390 0.476462 0.102 Uiso 1 1 calc R U . . .
C25 C 0.7718(2) 0.8715(2) 0.21234(19) 0.0484(5) Uani 1 1 d . . . . .
C26 C 0.9397(3) 0.9108(3) 0.1303(3) 0.0972(11) Uani 1 1 d . . . . .
H26A H 0.878244 0.872642 0.053194 0.117 Uiso 1 1 calc R U . . .
H26B H 0.952893 0.998537 0.137797 0.117 Uiso 1 1 calc R U . . .
C27 C 1.0604(4) 0.8829(5) 0.1460(5) 0.164(2) Uani 1 1 d . . . . .
H27A H 1.091729 0.905900 0.084375 0.245 Uiso 1 1 calc R U . . .
H27B H 1.047836 0.796643 0.144800 0.245 Uiso 1 1 calc R U . . .
H27C H 1.123158 0.927101 0.219444 0.245 Uiso 1 1 calc R U . . .
C28 C 0.48016(18) 0.60949(17) 0.16961(17) 0.0390(4) Uani 1 1 d . . . . .
C29 C 0.3613(3) 0.4190(2) 0.0477(3) 0.0721(8) Uani 1 1 d . . . . .
H29A H 0.294928 0.386708 -0.027224 0.108 Uiso 1 1 calc R U . . .
H29B H 0.335562 0.378917 0.105517 0.108 Uiso 1 1 calc R U . . .
H29C H 0.442256 0.405256 0.046059 0.108 Uiso 1 1 calc R U . . .
C30 C 0.31993(18) 0.74745(18) 0.00276(16) 0.0402(4) Uani 1 1 d . . . . .
C31 C 0.3030(3) 0.6856(4) -0.1905(2) 0.0993(11) Uani 1 1 d . . . . .
H31A H 0.354399 0.658828 -0.232224 0.149 Uiso 1 1 calc R U . . .
H31B H 0.270891 0.749786 -0.223690 0.149 Uiso 1 1 calc R U . . .
H31C H 0.230562 0.618151 -0.195661 0.149 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
N1 C1 C2 107.57(14) . . ?
O1 C1 N1 126.16(16) . . ?
O1 C1 C2 126.15(15) . . ?
C1 N1 C4 110.16(14) . . ?
C1 N1 C12 123.92(15) . . ?
C4 N1 C12 125.92(14) . . ?
C3 C2 C1 101.85(13) . . ?
C3 C2 C5 113.79(15) . . ?
O4 C2 C1 107.38(14) . . ?
O4 C2 C3 107.93(13) . . ?
O4 C2 C5 112.15(13) . . ?
C5 C2 C1 113.04(14) . . ?
C6 N2 C7 123.71(15) . . ?
C6 N2 C11 113.15(13) . . ?
C7 N2 C11 122.14(16) . . ?
C4 C3 C2 109.55(15) . . ?
C4 C3 C25 128.97(17) . . ?
C25 C3 C2 121.37(15) . . ?
C25 O3 C26 118.9(2) . . ?
N1 C4 C19 118.43(15) . . ?
C3 C4 N1 110.72(15) . . ?
C3 C4 C19 130.67(17) . . ?
C2 O4 C11 111.88(13) . . ?
C6 C5 C2 120.58(16) . . ?
C6 C5 C28 124.26(17) . . ?
C28 C5 C2 115.09(14) . . ?
N2 C6 C30 114.07(14) . . ?
C5 C6 N2 118.99(16) . . ?
C5 C6 C30 126.71(17) . . ?
C28 O6 C29 116.30(17) . . ?
N2 C7 H7 119.5 . . ?
C8 C7 N2 120.91(19) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.35(18) . . ?
C9 C8 H8 119.8 . . ?
C30 O8 C31 115.72(19) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.7(2) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 118.8 . . ?
C9 C10 C11 122.3(2) . . ?
C11 C10 H10 118.8 . . ?
N2 C11 C10 112.87(14) . . ?
N2 C11 H11 109.1 . . ?
O4 C11 N2 108.11(14) . . ?
O4 C11 C10 108.56(15) . . ?
O4 C11 H11 109.1 . . ?
C10 C11 H11 109.1 . . ?
C13 C12 N1 119.51(16) . . ?
C13 C12 C18 119.94(16) . . ?
C18 C12 N1 120.55(16) . . ?
C12 C13 H13 120.5 . . ?
C12 C13 C14 118.97(18) . . ?
C14 C13 H13 120.5 . . ?
C13 C14 H14 118.9 . . ?
C13 C14 C15 122.15(18) . . ?
C15 C14 H14 118.9 . . ?
C14 C15 C16 121.3(2) . . ?
C17 C15 C14 117.58(18) . . ?
C17 C15 C16 120.9(2) . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
H16B C16 H16C 109.5 . . ?
H16B C16 H16A 109.5 . . ?
H16C C16 H16A 109.5 . . ?
C15 C17 H17 119.3 . . ?
C15 C17 C18 121.4(2) . . ?
C18 C17 H17 119.3 . . ?
C12 C18 H18 120.1 . . ?
C17 C18 C12 119.90(19) . . ?
C17 C18 H18 120.1 . . ?
C20 C19 C4 119.13(18) . . ?
C24 C19 C4 123.27(18) . . ?
C24 C19 C20 117.60(19) . . ?
C19 C20 H20 119.6 . . ?
C19 C20 C21 120.9(2) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.6(2) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 120.3 . . ?
C23 C22 C21 119.4(2) . . ?
C23 C22 H22 120.3 . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C24 120.5(3) . . ?
C24 C23 H23 119.8 . . ?
C19 C24 C23 121.1(2) . . ?
C19 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
O2 C25 C3 123.93(19) . . ?
O2 C25 O3 122.77(19) . . ?
O3 C25 C3 113.31(17) . . ?
O3 C26 H26A 110.0 . . ?
O3 C26 H26B 110.0 . . ?
H26A C26 H26B 108.4 . . ?
C27 C26 O3 108.5(3) . . ?
C27 C26 H26A 110.0 . . ?
C27 C26 H26B 110.0 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O5 C28 C5 123.26(18) . . ?
O5 C28 O6 123.27(18) . . ?
O6 C28 C5 113.41(15) . . ?
O6 C29 H29A 109.5 . . ?
O6 C29 H29B 109.5 . . ?
O6 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O7 C30 C6 122.66(18) . . ?
O7 C30 O8 125.30(18) . . ?
O8 C30 C6 111.99(16) . . ?
O8 C31 H31A 109.5 . . ?
O8 C31 H31B 109.5 . . ?
O8 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 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
C1 N1 1.382(2) . ?
C1 O1 1.205(2) . ?
C1 C2 1.540(2) . ?
N1 C4 1.411(2) . ?
N1 C12 1.432(2) . ?
C2 C3 1.509(2) . ?
C2 O4 1.431(2) . ?
C2 C5 1.522(2) . ?
N2 C6 1.373(2) . ?
N2 C7 1.384(2) . ?
N2 C11 1.461(2) . ?
O2 C25 1.194(2) . ?
C3 C4 1.353(2) . ?
C3 C25 1.452(3) . ?
O3 C25 1.311(3) . ?
O3 C26 1.436(3) . ?
C4 C19 1.478(2) . ?
O4 C11 1.441(2) . ?
C5 C6 1.356(2) . ?
C5 C28 1.468(3) . ?
O5 C28 1.205(2) . ?
C6 C30 1.504(2) . ?
O6 C28 1.336(2) . ?
O6 C29 1.440(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.327(3) . ?
O7 C30 1.192(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.440(3) . ?
O8 C30 1.319(2) . ?
O8 C31 1.453(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.324(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.478(3) . ?
C11 H11 0.9800 . ?
C12 C13 1.377(3) . ?
C12 C18 1.381(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.379(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(3) . ?
C15 C16 1.508(3) . ?
C15 C17 1.374(3) . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 H16A 0.9600 . ?
C17 H17 0.9300 . ?
C17 C18 1.379(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.363(3) . ?
C19 C24 1.363(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.373(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.359(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.330(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.387(3) . ?
C24 H24 0.9300 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.419(5) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
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
C1 N1 C4 C3 3.5(2) . . . . ?
C1 N1 C4 C19 -172.11(16) . . . . ?
C1 N1 C12 C13 55.4(2) . . . . ?
C1 N1 C12 C18 -124.7(2) . . . . ?
C1 C2 C3 C4 -1.25(19) . . . . ?
C1 C2 C3 C25 175.28(18) . . . . ?
C1 C2 O4 C11 -95.43(15) . . . . ?
C1 C2 C5 C6 134.13(17) . . . . ?
C1 C2 C5 C28 -48.9(2) . . . . ?
N1 C1 C2 C3 3.26(18) . . . . ?
N1 C1 C2 O4 -110.02(15) . . . . ?
N1 C1 C2 C5 125.76(16) . . . . ?
N1 C4 C19 C20 67.8(3) . . . . ?
N1 C4 C19 C24 -112.6(3) . . . . ?
N1 C12 C13 C14 178.22(17) . . . . ?
N1 C12 C18 C17 -177.1(2) . . . . ?
O1 C1 N1 C4 179.72(18) . . . . ?
O1 C1 N1 C12 -0.4(3) . . . . ?
O1 C1 C2 C3 179.37(18) . . . . ?
O1 C1 C2 O4 66.1(2) . . . . ?
O1 C1 C2 C5 -58.1(2) . . . . ?
C2 C1 N1 C4 -4.2(2) . . . . ?
C2 C1 N1 C12 175.68(15) . . . . ?
C2 C3 C4 N1 -1.2(2) . . . . ?
C2 C3 C4 C19 173.71(18) . . . . ?
C2 C3 C25 O2 5.2(3) . . . . ?
C2 C3 C25 O3 -174.22(19) . . . . ?
C2 O4 C11 N2 -64.45(17) . . . . ?
C2 O4 C11 C10 172.79(14) . . . . ?
C2 C5 C6 N2 -19.0(2) . . . . ?
C2 C5 C6 C30 166.92(16) . . . . ?
C2 C5 C28 O5 -2.4(3) . . . . ?
C2 C5 C28 O6 175.13(15) . . . . ?
N2 C6 C30 O7 -58.4(2) . . . . ?
N2 C6 C30 O8 119.20(18) . . . . ?
N2 C7 C8 C9 2.0(3) . . . . ?
C3 C2 O4 C11 155.46(13) . . . . ?
C3 C2 C5 C6 -110.32(18) . . . . ?
C3 C2 C5 C28 66.69(19) . . . . ?
C3 C4 C19 C20 -106.8(3) . . . . ?
C3 C4 C19 C24 72.8(3) . . . . ?
C4 N1 C12 C13 -124.8(2) . . . . ?
C4 N1 C12 C18 55.1(3) . . . . ?
C4 C3 C25 O2 -179.0(2) . . . . ?
C4 C3 C25 O3 1.6(3) . . . . ?
C4 C19 C20 C21 179.7(2) . . . . ?
C4 C19 C24 C23 178.7(3) . . . . ?
O4 C2 C3 C4 111.63(16) . . . . ?
O4 C2 C3 C25 -71.8(2) . . . . ?
O4 C2 C5 C6 12.6(2) . . . . ?
O4 C2 C5 C28 -170.44(15) . . . . ?
C5 C2 C3 C4 -123.22(17) . . . . ?
C5 C2 C3 C25 53.3(2) . . . . ?
C5 C2 O4 C11 29.33(19) . . . . ?
C5 C6 C30 O7 115.9(2) . . . . ?
C5 C6 C30 O8 -66.5(2) . . . . ?
C6 N2 C7 C8 -176.09(19) . . . . ?
C6 N2 C11 O4 58.64(18) . . . . ?
C6 N2 C11 C10 178.73(16) . . . . ?
C6 C5 C28 O5 174.52(19) . . . . ?
C6 C5 C28 O6 -8.0(3) . . . . ?
C7 N2 C6 C5 151.68(17) . . . . ?
C7 N2 C6 C30 -33.5(2) . . . . ?
C7 N2 C11 O4 -110.29(17) . . . . ?
C7 N2 C11 C10 9.8(2) . . . . ?
C7 C8 C9 C10 2.1(4) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C9 C10 C11 N2 -5.7(3) . . . . ?
C9 C10 C11 O4 114.1(2) . . . . ?
C11 N2 C6 C5 -17.1(2) . . . . ?
C11 N2 C6 C30 157.72(15) . . . . ?
C11 N2 C7 C8 -8.3(3) . . . . ?
C12 N1 C4 C3 -176.36(17) . . . . ?
C12 N1 C4 C19 8.0(3) . . . . ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C13 C12 C18 C17 2.8(3) . . . . ?
C13 C14 C15 C16 -173.8(2) . . . . ?
C13 C14 C15 C17 2.1(3) . . . . ?
C14 C15 C17 C18 -0.9(4) . . . . ?
C15 C17 C18 C12 -1.4(4) . . . . ?
C16 C15 C17 C18 175.0(3) . . . . ?
C18 C12 C13 C14 -1.7(3) . . . . ?
C19 C20 C21 C22 0.7(5) . . . . ?
C20 C19 C24 C23 -1.6(5) . . . . ?
C20 C21 C22 C23 0.1(5) . . . . ?
C21 C22 C23 C24 -1.7(6) . . . . ?
C22 C23 C24 C19 2.4(6) . . . . ?
C24 C19 C20 C21 0.1(4) . . . . ?
C25 C3 C4 N1 -177.38(19) . . . . ?
C25 C3 C4 C19 -2.5(4) . . . . ?
C25 O3 C26 C27 -173.7(3) . . . . ?
C26 O3 C25 O2 0.4(4) . . . . ?
C26 O3 C25 C3 179.8(3) . . . . ?
C28 C5 C6 N2 164.24(16) . . . . ?
C28 C5 C6 C30 -9.8(3) . . . . ?
C29 O6 C28 C5 -177.41(19) . . . . ?
C29 O6 C28 O5 0.1(3) . . . . ?
C31 O8 C30 C6 -178.4(2) . . . . ?
C31 O8 C30 O7 -0.9(3) . . . . ?
