#------------------------------------------------------------------------------
#$Date: 2022-05-05 23:56:13 +0300 (Thu, 05 May 2022) $
#$Revision: 275070 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/40/7244093.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_7244093
loop_
_publ_author_name
'Cossío, Fernando P'
'de Cózar, Abel'
'Sierra, Miguel A.'
'Casarrubios, Luis'
'Muntaner, Jaime G.'
'Banik, Bimal K.'
'Bandyopadhyay, Debasish'
_publ_section_title
;
 Role of imine isomerization in the stereocontrol of the Staudinger
 reaction between ketenes and imines.
;
_journal_issue                   1
_journal_name_full               'RSC advances'
_journal_page_first              104
_journal_page_last               117
_journal_paper_doi               10.1039/d1ra06114c
_journal_volume                  12
_journal_year                    2021
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H18 N2 O5'
_chemical_formula_sum            'C20 H18 N2 O5'
_chemical_formula_weight         366.36
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2009-10-13T13:03:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2019-09-04 deposited with the CCDC.	2021-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.49(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.945(4)
_cell_length_b                   8.7506(13)
_cell_length_c                   21.976(4)
_cell_measurement_reflns_used    2973
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.0205
_cell_measurement_theta_min      2.7906
_cell_measurement_wavelength     0.71073
_cell_volume                     3604.9(13)
_computing_cell_refinement
'CrysAlis Pro (Oxford Diffraction Ltd., 2009)'
_computing_data_collection
'CrysAlis Pro (Oxford Diffraction Ltd., 2009)'
_computing_data_reduction
'CrysAlis Pro (Oxford Diffraction Ltd., 2009)'
_computing_molecular_graphics    'Diamond v.3.1f (Crystal Impact GbR, 2008)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Giacovazzo et al, 2005)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.3504
_diffrn_detector_type            'Sapphire2 (large Be window)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -13.00   44.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -       22.0540   77.0000 -150.0000 57

#__ type_ start__ end____ width___ exp.time_
  2 omega    3.00  119.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -       22.0540   77.0000  -60.0000 116

#__ type_ start__ end____ width___ exp.time_
  3 omega  -10.00   56.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -       22.0540   77.0000   60.0000 66

#__ type_ start__ end____ width___ exp.time_
  4 omega  -40.00    4.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.6634  -37.0000 -180.0000 44

#__ type_ start__ end____ width___ exp.time_
  5 omega  -21.00   14.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.6634  -88.0000   92.0000 35

#__ type_ start__ end____ width___ exp.time_
  6 omega  -61.00  -29.00   1.0000  240.0000
omega____ theta____ kappa____ phi______ frames
    -       22.0540  -37.0000  -30.0000 32

;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur 2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0230103137
_diffrn_orient_matrix_UB_12      -0.0631520395
_diffrn_orient_matrix_UB_13      0.01430983
_diffrn_orient_matrix_UB_21      -0.0265932364
_diffrn_orient_matrix_UB_22      -0.035839417
_diffrn_orient_matrix_UB_23      0.0066727154
_diffrn_orient_matrix_UB_31      -0.0144430892
_diffrn_orient_matrix_UB_32      -0.0352138266
_diffrn_orient_matrix_UB_33      -0.0326336056
_diffrn_radiation_collimation    '0.5 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0801
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18733
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.92191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.48 (release 15-09-2009 CrysAlis171 .NET)
        (compiled Sep 15 2009,11:49:04)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.35
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Cut prism'
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.353
_exptl_crystal_size_mid          0.2717
_exptl_crystal_size_min          0.0733
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.829
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     520
_refine_ls_number_reflns         6336
_refine_ls_number_restraints     94
_refine_ls_restrained_S_all      0.823
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0384
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0345P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0764
_reflns_number_gt                3782
_reflns_number_total             6336
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            d1ra06114c2.cif
_cod_data_source_block           maria1
_cod_depositor_comments
'Adding full bibliography for 7244093--7244094.cif.'
_cod_original_cell_volume        3604.9(11)
_cod_database_code               7244093
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
N1 N 0.36685(7) -0.00268(15) 0.64074(7) 0.0164(3) Uani 1 1 d . . .
N2 N 0.30048(7) 0.12389(16) 0.47004(7) 0.0164(4) Uani 1 1 d . . .
O1 O 0.44624(6) -0.19324(13) 0.70850(6) 0.0260(3) Uani 1 1 d . . .
O2 O 0.14015(7) 0.08922(14) 0.70290(6) 0.0268(3) Uani 1 1 d . . .
O3 O 0.29845(6) -0.12788(14) 0.49825(6) 0.0210(3) Uani 1 1 d . . .
O4 O 0.45319(6) -0.15042(13) 0.56950(6) 0.0226(3) Uani 1 1 d . . .
O5 O 0.55589(8) -0.05513(18) 0.57678(9) 0.0565(5) Uani 1 1 d . . .
C2 C 0.37674(9) 0.05706(19) 0.58277(8) 0.0164(4) Uani 1 1 d . . .
C3 C 0.44844(10) -0.03686(19) 0.61251(9) 0.0199(4) Uani 1 1 d . . .
H3 H 0.4919 0.029 0.6335 0.024 Uiso 1 1 calc R . .
C4 C 0.42447(10) -0.0978(2) 0.66380(9) 0.0199(4) Uani 1 1 d . . .
C5 C 0.31077(9) 0.02155(19) 0.65869(8) 0.0176(4) Uani 1 1 d . . .
C6 C 0.30467(10) -0.0700(2) 0.70731(9) 0.0220(5) Uani 1 1 d . . .
H6 H 0.3393 -0.1469 0.7298 0.026 Uiso 1 1 calc R . .
C7 C 0.24857(10) -0.0498(2) 0.72312(9) 0.0234(5) Uani 1 1 d . . .
H7 H 0.2447 -0.1131 0.7564 0.028 Uiso 1 1 calc R . .
C8 C 0.19765(10) 0.0618(2) 0.69098(9) 0.0206(4) Uani 1 1 d . . .
C9 C 0.20417(10) 0.1544(2) 0.64295(9) 0.0194(4) Uani 1 1 d . . .
H9 H 0.1697 0.2318 0.6209 0.023 Uiso 1 1 calc R . .
C10 C 0.26002(9) 0.13529(19) 0.62690(8) 0.0184(4) Uani 1 1 d . . .
H10 H 0.2641 0.1998 0.594 0.022 Uiso 1 1 calc R . .
C11 C 0.13038(11) -0.0063(2) 0.75044(10) 0.0320(5) Uani 1 1 d . . .
H11A H 0.173 -0.0019 0.7943 0.048 Uiso 1 1 calc R . .
H11B H 0.1225 -0.1118 0.7337 0.048 Uiso 1 1 calc R . .
H11C H 0.0889 0.029 0.7561 0.048 Uiso 1 1 calc R . .
C12 C 0.32042(9) 0.0018(2) 0.51247(9) 0.0164(4) Uani 1 1 d . . .
C13 C 0.33397(9) 0.2575(2) 0.50559(8) 0.0151(4) Uani 1 1 d . . .
C14 C 0.37863(9) 0.22478(19) 0.57341(8) 0.0148(4) Uani 1 1 d . . .
C15 C 0.41547(9) 0.3389(2) 0.61872(9) 0.0182(4) Uani 1 1 d . . .
H15 H 0.4459 0.3169 0.6651 0.022 Uiso 1 1 calc R . .
C16 C 0.40642(9) 0.4869(2) 0.59405(9) 0.0202(4) Uani 1 1 d . . .
H16 H 0.4308 0.5684 0.624 0.024 Uiso 1 1 calc R . .
C17 C 0.36208(9) 0.5177(2) 0.52612(9) 0.0199(4) Uani 1 1 d . . .
H17 H 0.357 0.6203 0.5105 0.024 Uiso 1 1 calc R . .
C18 C 0.32490(9) 0.40257(19) 0.48021(9) 0.0178(4) Uani 1 1 d . . .
H18 H 0.2948 0.4238 0.4337 0.021 Uiso 1 1 calc R . .
C19 C 0.25035(10) 0.1177(2) 0.39829(8) 0.0251(5) Uani 1 1 d . . .
H19A H 0.23 0.0148 0.3868 0.038 Uiso 1 1 calc R . .
H19B H 0.2752 0.1423 0.3709 0.038 Uiso 1 1 calc R . .
H19C H 0.212 0.192 0.3888 0.038 Uiso 1 1 calc R . .
C20 C 0.50948(11) -0.1484(2) 0.55457(11) 0.0329(5) Uani 1 1 d . . .
C21 C 0.50304(12) -0.2764(2) 0.50777(12) 0.0443(6) Uani 1 1 d . . .
H21A H 0.5486 -0.2904 0.5059 0.066 Uiso 1 1 calc R . .
H21B H 0.4656 -0.2528 0.4622 0.066 Uiso 1 1 calc R . .
H21C H 0.4907 -0.3704 0.5243 0.066 Uiso 1 1 calc R . .
N31 N 0.38557(8) 0.02487(16) 0.17154(7) 0.0177(4) Uani 1 1 d . . .
N32 N 0.33130(8) 0.13347(16) 0.00155(7) 0.0191(4) Uani 1 1 d . . .
O31 O 0.46166(6) -0.15835(14) 0.24876(6) 0.0262(3) Uani 1 1 d . . .
O32 O 0.12928(7) 0.10683(14) 0.18484(6) 0.0260(3) Uani 1 1 d . . .
O33 O 0.33133(6) -0.11639(14) 0.03281(6) 0.0245(3) Uani 1 1 d . . .
C32 C 0.40281(9) 0.0771(2) 0.11696(9) 0.0183(4) Uani 1 1 d . . .
C34 C 0.44373(10) -0.0681(2) 0.20218(9) 0.0196(4) Uani 1 1 d . . .
C35 C 0.32275(9) 0.04772(19) 0.17930(8) 0.0161(4) Uani 1 1 d . . .
C36 C 0.30669(10) -0.0460(2) 0.22108(9) 0.0207(4) Uani 1 1 d . . .
H36 H 0.3397 -0.1221 0.2477 0.025 Uiso 1 1 calc R . .
C37 C 0.24256(10) -0.0290(2) 0.22418(9) 0.0216(5) Uani 1 1 d . . .
H37 H 0.2316 -0.0944 0.2527 0.026 Uiso 1 1 calc R . .
C38 C 0.19422(9) 0.0822(2) 0.18612(9) 0.0187(4) Uani 1 1 d . . .
C39 C 0.21151(9) 0.17898(19) 0.14561(8) 0.0183(4) Uani 1 1 d . . .
H39 H 0.1793 0.2575 0.1203 0.022 Uiso 1 1 calc R . .
C40 C 0.27492(9) 0.16189(19) 0.14193(8) 0.0172(4) Uani 1 1 d . . .
H40 H 0.2862 0.2281 0.1138 0.021 Uiso 1 1 calc R . .
C41 C 0.10675(10) 0.0033(2) 0.22130(9) 0.0307(5) Uani 1 1 d . . .
H41A H 0.1409 0.0051 0.2696 0.046 Uiso 1 1 calc R . .
H41B H 0.1042 -0.1002 0.2033 0.046 Uiso 1 1 calc R . .
H41C H 0.0595 0.0336 0.2161 0.046 Uiso 1 1 calc R . .
C42 C 0.35110(9) 0.0143(2) 0.04609(9) 0.0182(4) Uani 1 1 d . . .
C43 C 0.36246(9) 0.2702(2) 0.03554(9) 0.0173(4) Uani 1 1 d . . .
C44 C 0.40478(9) 0.2433(2) 0.10441(9) 0.0167(4) Uani 1 1 d . . .
C45 C 0.43942(10) 0.3610(2) 0.14820(9) 0.0218(5) Uani 1 1 d . . .
H45 H 0.4685 0.3426 0.1952 0.026 Uiso 1 1 calc R . .
C46 C 0.43057(10) 0.5068(2) 0.12162(10) 0.0245(5) Uani 1 1 d . . .
H46 H 0.4535 0.5905 0.1507 0.029 Uiso 1 1 calc R . .
C47 C 0.38829(9) 0.5319(2) 0.05251(10) 0.0253(5) Uani 1 1 d . . .
H47 H 0.383 0.6332 0.0353 0.03 Uiso 1 1 calc R . .
C48 C 0.35365(10) 0.4134(2) 0.00797(9) 0.0221(5) Uani 1 1 d . . .
H48 H 0.3253 0.4308 -0.0392 0.027 Uiso 1 1 calc R . .
C49 C 0.27921(10) 0.1211(2) -0.06953(9) 0.0282(5) Uani 1 1 d . . .
H49A H 0.2404 0.1941 -0.079 0.042 Uiso 1 1 calc R . .
H49B H 0.2598 0.0171 -0.0787 0.042 Uiso 1 1 calc R . .
H49C H 0.3024 0.1437 -0.0987 0.042 Uiso 1 1 calc R . .
C33 C 0.47479(10) -0.01299(19) 0.15533(9) 0.0208(4) Uani 1 1 d DU A .
H33 H 0.5169 0.0558 0.1787 0.025 Uiso 1 1 calc R . .
O34 O 0.48839(7) -0.13441(13) 0.12078(6) 0.0249(3) Uani 1 1 d DU . .
O35A O 0.5670(7) 0.0074(11) 0.1038(7) 0.073(3) Uani 0.516(17) 1 d PDU A 1
C50A C 0.5375(6) -0.1117(12) 0.0980(6) 0.039(3) Uani 0.516(17) 1 d PDU A 1
C51A C 0.5487(5) -0.2535(11) 0.0678(5) 0.038(2) Uani 0.516(17) 1 d PDU A 1
H51A H 0.5158 -0.3325 0.0685 0.056 Uiso 0.516(17) 1 calc PR A 1
H51B H 0.598 -0.2883 0.0941 0.056 Uiso 0.516(17) 1 calc PR A 1
H51C H 0.5397 -0.2339 0.0207 0.056 Uiso 0.516(17) 1 calc PR A 1
O35B O 0.5242(7) 0.0350(6) 0.0680(6) 0.062(3) Uani 0.484(17) 1 d PDU A 2
C50B C 0.5146(7) -0.0957(12) 0.0764(7) 0.042(3) Uani 0.484(17) 1 d PDU A 2
C51B C 0.5239(8) -0.2299(12) 0.0395(7) 0.060(3) Uani 0.484(17) 1 d PDU A 2
H51D H 0.5106 -0.3233 0.0557 0.09 Uiso 0.484(17) 1 calc PR A 2
H51E H 0.5739 -0.2367 0.048 0.09 Uiso 0.484(17) 1 calc PR A 2
H51F H 0.4934 -0.218 -0.0093 0.09 Uiso 0.484(17) 1 calc PR A 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
29 1 -16 0.0282
-29 0 19 0.0286
-27 1 24 0.0274
5 -12 -8 0.1329
2 -5 -26 0.1112
-6 9 -16 0.1242
-6 12 6 0.1319
0 1 27 0.1271
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
C4 N1 C5 134.14(15) . . ?
C4 N1 C2 95.46(14) . . ?
C5 N1 C2 130.02(14) . . ?
C12 N2 C13 110.40(14) . . ?
C12 N2 C19 124.65(15) . . ?
C13 N2 C19 124.94(14) . . ?
C8 O2 C11 117.83(14) . . ?
C20 O4 C3 118.87(15) . . ?
N1 C2 C14 119.52(14) . . ?
N1 C2 C12 114.47(14) . . ?
C14 C2 C12 103.10(14) . . ?
N1 C2 C3 86.10(12) . . ?
C14 C2 C3 119.57(14) . . ?
C12 C2 C3 114.38(14) . . ?
O4 C3 C4 113.35(14) . . ?
O4 C3 C2 115.49(14) . . ?
C4 C3 C2 85.50(13) . . ?
O4 C3 H3 113.2 . . ?
C4 C3 H3 113.2 . . ?
C2 C3 H3 113.2 . . ?
O1 C4 N1 132.21(18) . . ?
O1 C4 C3 135.46(17) . . ?
N1 C4 C3 92.33(14) . . ?
C6 C5 C10 119.14(18) . . ?
C6 C5 N1 120.17(16) . . ?
C10 C5 N1 120.68(16) . . ?
C7 C6 C5 120.15(17) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 120.76(17) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
O2 C8 C9 116.09(16) . . ?
O2 C8 C7 124.83(17) . . ?
C9 C8 C7 119.08(18) . . ?
C10 C9 C8 120.61(17) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C5 120.25(17) . . ?
C9 C10 H10 119.9 . . ?
C5 C10 H10 119.9 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 N2 126.55(16) . . ?
O3 C12 C2 125.71(16) . . ?
N2 C12 C2 107.73(15) . . ?
C18 C13 C14 122.25(16) . . ?
C18 C13 N2 126.99(16) . . ?
C14 C13 N2 110.75(15) . . ?
C15 C14 C13 121.15(16) . . ?
C15 C14 C2 131.09(16) . . ?
C13 C14 C2 107.76(15) . . ?
C14 C15 C16 117.42(16) . . ?
C14 C15 H15 121.3 . . ?
C16 C15 H15 121.3 . . ?
C15 C16 C17 120.78(17) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C16 C17 C18 121.93(17) . . ?
C16 C17 H17 119 . . ?
C18 C17 H17 119 . . ?
C13 C18 C17 116.47(16) . . ?
C13 C18 H18 121.8 . . ?
C17 C18 H18 121.8 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O5 C20 O4 123.1(2) . . ?
O5 C20 C21 127.2(2) . . ?
O4 C20 C21 109.69(17) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C34 N31 C35 134.23(15) . . ?
C34 N31 C32 95.61(14) . . ?
C35 N31 C32 129.36(14) . . ?
C42 N32 C43 110.43(14) . . ?
C42 N32 C49 123.78(15) . . ?
C43 N32 C49 125.49(15) . . ?
C38 O32 C41 117.77(14) . . ?
N31 C32 C44 119.57(14) . . ?
N31 C32 C42 113.18(14) . . ?
C44 C32 C42 103.07(14) . . ?
N31 C32 C33 86.11(13) . . ?
C44 C32 C33 119.45(15) . . ?
C42 C32 C33 115.76(14) . . ?
O31 C34 N31 132.55(18) . . ?
O31 C34 C33 135.49(17) . . ?
N31 C34 C33 91.97(14) . . ?
C36 C35 C40 119.57(17) . . ?
C36 C35 N31 120.82(16) . . ?
C40 C35 N31 119.55(15) . . ?
C35 C36 C37 119.97(17) . . ?
C35 C36 H36 120 . . ?
C37 C36 H36 120 . . ?
C36 C37 C38 120.67(17) . . ?
C36 C37 H37 119.7 . . ?
C38 C37 H37 119.7 . . ?
O32 C38 C37 125.23(16) . . ?
O32 C38 C39 115.67(16) . . ?
C37 C38 C39 119.11(17) . . ?
C40 C39 C38 120.44(17) . . ?
C40 C39 H39 119.8 . . ?
C38 C39 H39 119.8 . . ?
C39 C40 C35 120.20(16) . . ?
C39 C40 H40 119.9 . . ?
C35 C40 H40 119.9 . . ?
O32 C41 H41A 109.5 . . ?
O32 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
O32 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
O33 C42 N32 126.15(17) . . ?
O33 C42 C32 126.20(16) . . ?
N32 C42 C32 107.64(15) . . ?
C48 C43 C44 122.13(17) . . ?
C48 C43 N32 127.19(16) . . ?
C44 C43 N32 110.67(15) . . ?
C45 C44 C43 121.05(17) . . ?
C45 C44 C32 130.81(16) . . ?
C43 C44 C32 108.14(15) . . ?
C44 C45 C46 117.81(17) . . ?
C44 C45 H45 121.1 . . ?
C46 C45 H45 121.1 . . ?
C45 C46 C47 120.49(17) . . ?
C45 C46 H46 119.8 . . ?
C47 C46 H46 119.8 . . ?
C48 C47 C46 121.95(17) . . ?
C48 C47 H47 119 . . ?
C46 C47 H47 119 . . ?
C43 C48 C47 116.56(17) . . ?
C43 C48 H48 121.7 . . ?
C47 C48 H48 121.7 . . ?
N32 C49 H49A 109.5 . . ?
N32 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
N32 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
O34 C33 C34 112.14(14) . . ?
O34 C33 C32 117.77(14) . . ?
C34 C33 C32 85.68(13) . . ?
O34 C33 H33 112.8 . . ?
C34 C33 H33 112.8 . . ?
C32 C33 H33 112.8 . . ?
C50A O34 C33 117.5(4) . . ?
C50B O34 C33 116.3(4) . . ?
O35A C50A O34 122.5(8) . . ?
O35A C50A C51A 127.3(7) . . ?
O34 C50A C51A 110.2(7) . . ?
C50A C51A H51A 109.5 . . ?
C50A C51A H51B 109.5 . . ?
H51A C51A H51B 109.5 . . ?
C50A C51A H51C 109.5 . . ?
H51A C51A H51C 109.5 . . ?
H51B C51A H51C 109.5 . . ?
O35B C50B O34 120.2(8) . . ?
O35B C50B C51B 126.8(9) . . ?
O34 C50B C51B 112.8(8) . . ?
C50B C51B H51D 109.5 . . ?
C50B C51B H51E 109.5 . . ?
H51D C51B H51E 109.5 . . ?
C50B C51B H51F 109.5 . . ?
H51D C51B H51F 109.5 . . ?
H51E C51B H51F 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
N1 C4 1.364(2) . ?
N1 C5 1.412(2) . ?
N1 C2 1.475(2) . ?
N2 C12 1.356(2) . ?
N2 C13 1.407(2) . ?
N2 C19 1.454(2) . ?
O1 C4 1.213(2) . ?
O2 C8 1.363(2) . ?
O2 C11 1.422(2) . ?
O3 C12 1.2118(19) . ?
O4 C20 1.358(2) . ?
O4 C3 1.405(2) . ?
O5 C20 1.194(2) . ?
C2 C14 1.485(2) . ?
C2 C12 1.545(2) . ?
C2 C3 1.576(2) . ?
C3 C4 1.520(2) . ?
C3 H3 1 . ?
C5 C6 1.386(2) . ?
C5 C10 1.395(2) . ?
C6 C7 1.377(2) . ?
C6 H6 0.95 . ?
C7 C8 1.385(2) . ?
C7 H7 0.95 . ?
C8 C9 1.384(2) . ?
C9 C10 1.374(2) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C13 C18 1.365(2) . ?
C13 C14 1.391(2) . ?
C14 C15 1.378(2) . ?
C15 C16 1.384(2) . ?
C15 H15 0.95 . ?
C16 C17 1.388(2) . ?
C16 H16 0.95 . ?
C17 C18 1.392(2) . ?
C17 H17 0.95 . ?
C18 H18 0.95 . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C20 C21 1.486(3) . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
N31 C34 1.366(2) . ?
N31 C35 1.414(2) . ?
N31 C32 1.471(2) . ?
N32 C42 1.362(2) . ?
N32 C43 1.408(2) . ?
N32 C49 1.456(2) . ?
O31 C34 1.213(2) . ?
O32 C38 1.365(2) . ?
O32 C41 1.422(2) . ?
O33 C42 1.207(2) . ?
C32 C44 1.484(2) . ?
C32 C42 1.548(2) . ?
C32 C33 1.572(2) . ?
C34 C33 1.521(3) . ?
C35 C36 1.380(2) . ?
C35 C40 1.394(2) . ?
C36 C37 1.383(2) . ?
C36 H36 0.95 . ?
C37 C38 1.385(2) . ?
C37 H37 0.95 . ?
C38 C39 1.389(2) . ?
C39 C40 1.374(2) . ?
C39 H39 0.95 . ?
C40 H40 0.95 . ?
C41 H41A 0.98 . ?
C41 H41B 0.98 . ?
C41 H41C 0.98 . ?
C43 C48 1.368(2) . ?
C43 C44 1.391(2) . ?
C44 C45 1.375(2) . ?
C45 C46 1.381(2) . ?
C45 H45 0.95 . ?
C46 C47 1.393(2) . ?
C46 H46 0.95 . ?
C47 C48 1.388(2) . ?
C47 H47 0.95 . ?
C48 H48 0.95 . ?
C49 H49A 0.98 . ?
C49 H49B 0.98 . ?
C49 H49C 0.98 . ?
C33 O34 1.407(2) . ?
C33 H33 1 . ?
O34 C50A 1.345(8) . ?
O34 C50B 1.357(9) . ?
O35A C50A 1.190(8) . ?
C50A C51A 1.474(9) . ?
C51A H51A 0.98 . ?
C51A H51B 0.98 . ?
C51A H51C 0.98 . ?
O35B C50B 1.191(9) . ?
C50B C51B 1.489(9) . ?
C51B H51D 0.98 . ?
C51B H51E 0.98 . ?
C51B H51F 0.98 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3 H3 O5 1.0000 2.3200 2.699(3) 101.00 . yes
C3 H3 O31 1.0000 2.5800 3.262(2) 125.00 3_656 yes
C6 H6 O1 0.9500 2.5200 3.144(3) 124.00 . yes
C15 H15 O31 0.9500 2.4500 3.304(2) 150.00 3_656 yes
C17 H17 O3 0.9500 2.4800 3.323(2) 148.00 1_565 yes
C19 H19A O3 0.9800 2.5500 2.913(2) 102.00 . yes
C33 H33 O1 1.0000 2.5500 3.245(2) 127.00 3_656 yes
C36 H36 O31 0.9500 2.5600 3.180(3) 123.00 . yes
C45 H45 O1 0.9500 2.4500 3.329(2) 154.00 3_656 yes
C47 H47 O33 0.9500 2.4300 3.259(2) 145.00 1_565 yes
C49 H49B O33 0.9800 2.5200 2.895(2) 103.00 . yes
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
C4 N1 C2 C14 -128.04(16) . . . . ?
C5 N1 C2 C14 58.4(2) . . . . ?
C4 N1 C2 C12 109.02(16) . . . . ?
C5 N1 C2 C12 -64.6(2) . . . . ?
C4 N1 C2 C3 -6.04(13) . . . . ?
C5 N1 C2 C3 -179.64(16) . . . . ?
C20 O4 C3 C4 -138.48(17) . . . . ?
C20 O4 C3 C2 125.14(17) . . . . ?
N1 C2 C3 O4 119.17(15) . . . . ?
C14 C2 C3 O4 -118.88(17) . . . . ?
C12 C2 C3 O4 4.0(2) . . . . ?
N1 C2 C3 C4 5.41(12) . . . . ?
C14 C2 C3 C4 127.36(16) . . . . ?
C12 C2 C3 C4 -109.74(15) . . . . ?
C5 N1 C4 O1 -0.5(3) . . . . ?
C2 N1 C4 O1 -173.72(19) . . . . ?
C5 N1 C4 C3 179.42(18) . . . . ?
C2 N1 C4 C3 6.25(14) . . . . ?
O4 C3 C4 O1 58.3(3) . . . . ?
C2 C3 C4 O1 174.1(2) . . . . ?
O4 C3 C4 N1 -121.70(15) . . . . ?
C2 C3 C4 N1 -5.84(13) . . . . ?
C4 N1 C5 C6 -4.4(3) . . . . ?
C2 N1 C5 C6 166.69(16) . . . . ?
C4 N1 C5 C10 176.95(17) . . . . ?
C2 N1 C5 C10 -11.9(3) . . . . ?
C10 C5 C6 C7 0.9(3) . . . . ?
N1 C5 C6 C7 -177.77(15) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C11 O2 C8 C9 178.20(15) . . . . ?
C11 O2 C8 C7 -1.8(2) . . . . ?
C6 C7 C8 O2 179.43(16) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
O2 C8 C9 C10 -179.55(15) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C8 C9 C10 C5 0.3(3) . . . . ?
C6 C5 C10 C9 -1.0(2) . . . . ?
N1 C5 C10 C9 177.64(15) . . . . ?
C13 N2 C12 O3 176.26(17) . . . . ?
C19 N2 C12 O3 -2.5(3) . . . . ?
C13 N2 C12 C2 -3.89(18) . . . . ?
C19 N2 C12 C2 177.34(15) . . . . ?
N1 C2 C12 O3 -43.7(2) . . . . ?
C14 C2 C12 O3 -175.11(16) . . . . ?
C3 C2 C12 O3 53.5(2) . . . . ?
N1 C2 C12 N2 136.46(14) . . . . ?
C14 C2 C12 N2 5.04(17) . . . . ?
C3 C2 C12 N2 -126.40(15) . . . . ?
C12 N2 C13 C18 -177.58(17) . . . . ?
C19 N2 C13 C18 1.2(3) . . . . ?
C12 N2 C13 C14 1.08(19) . . . . ?
C19 N2 C13 C14 179.85(16) . . . . ?
C18 C13 C14 C15 0.8(3) . . . . ?
N2 C13 C14 C15 -177.94(15) . . . . ?
C18 C13 C14 C2 -178.92(16) . . . . ?
N2 C13 C14 C2 2.34(18) . . . . ?
N1 C2 C14 C15 47.6(3) . . . . ?
C12 C2 C14 C15 175.97(18) . . . . ?
C3 C2 C14 C15 -55.8(3) . . . . ?
N1 C2 C14 C13 -132.70(16) . . . . ?
C12 C2 C14 C13 -4.35(17) . . . . ?
C3 C2 C14 C13 123.92(16) . . . . ?
C13 C14 C15 C16 -0.2(2) . . . . ?
C2 C14 C15 C16 179.46(17) . . . . ?
C14 C15 C16 C17 -0.3(2) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?
C14 C13 C18 C17 -0.9(2) . . . . ?
N2 C13 C18 C17 177.66(16) . . . . ?
C16 C17 C18 C13 0.4(3) . . . . ?
C3 O4 C20 O5 0.7(3) . . . . ?
C3 O4 C20 C21 -179.09(15) . . . . ?
C34 N31 C32 C44 -128.09(16) . . . . ?
C35 N31 C32 C44 61.1(2) . . . . ?
C34 N31 C32 C42 110.19(15) . . . . ?
C35 N31 C32 C42 -60.6(2) . . . . ?
C34 N31 C32 C33 -6.22(13) . . . . ?
C35 N31 C32 C33 -176.98(16) . . . . ?
C35 N31 C34 O31 -3.5(3) . . . . ?
C32 N31 C34 O31 -173.55(19) . . . . ?
C35 N31 C34 C33 176.44(17) . . . . ?
C32 N31 C34 C33 6.42(14) . . . . ?
C34 N31 C35 C36 -7.2(3) . . . . ?
C32 N31 C35 C36 159.92(16) . . . . ?
C34 N31 C35 C40 175.72(17) . . . . ?
C32 N31 C35 C40 -17.2(2) . . . . ?
C40 C35 C36 C37 1.8(2) . . . . ?
N31 C35 C36 C37 -175.25(15) . . . . ?
C35 C36 C37 C38 -0.6(3) . . . . ?
C41 O32 C38 C37 -5.0(2) . . . . ?
C41 O32 C38 C39 175.21(15) . . . . ?
C36 C37 C38 O32 179.03(16) . . . . ?
C36 C37 C38 C39 -1.2(3) . . . . ?
O32 C38 C39 C40 -178.50(15) . . . . ?
C37 C38 C39 C40 1.7(2) . . . . ?
C38 C39 C40 C35 -0.4(2) . . . . ?
C36 C35 C40 C39 -1.3(2) . . . . ?
N31 C35 C40 C39 175.78(15) . . . . ?
C43 N32 C42 O33 177.43(17) . . . . ?
C49 N32 C42 O33 3.4(3) . . . . ?
C43 N32 C42 C32 -1.91(18) . . . . ?
C49 N32 C42 C32 -175.91(15) . . . . ?
N31 C32 C42 O33 -46.3(2) . . . . ?
C44 C32 C42 O33 -176.89(17) . . . . ?
C33 C32 C42 O33 50.9(2) . . . . ?
N31 C32 C42 N32 133.03(15) . . . . ?
C44 C32 C42 N32 2.45(17) . . . . ?
C33 C32 C42 N32 -129.81(16) . . . . ?
C42 N32 C43 C48 -178.45(17) . . . . ?
C49 N32 C43 C48 -4.6(3) . . . . ?
C42 N32 C43 C44 0.55(19) . . . . ?
C49 N32 C43 C44 174.43(16) . . . . ?
C48 C43 C44 C45 0.5(3) . . . . ?
N32 C43 C44 C45 -178.51(15) . . . . ?
C48 C43 C44 C32 -179.82(16) . . . . ?
N32 C43 C44 C32 1.12(19) . . . . ?
N31 C32 C44 C45 50.9(3) . . . . ?
C42 C32 C44 C45 177.48(18) . . . . ?
C33 C32 C44 C45 -52.5(3) . . . . ?
N31 C32 C44 C43 -128.72(17) . . . . ?
C42 C32 C44 C43 -2.11(17) . . . . ?
C33 C32 C44 C43 127.94(17) . . . . ?
C43 C44 C45 C46 0.3(3) . . . . ?
C32 C44 C45 C46 -179.28(17) . . . . ?
C44 C45 C46 C47 -0.5(3) . . . . ?
C45 C46 C47 C48 0.1(3) . . . . ?
C44 C43 C48 C47 -1.0(2) . . . . ?
N32 C43 C48 C47 177.89(17) . . . . ?
C46 C47 C48 C43 0.7(3) . . . . ?
O31 C34 C33 O34 55.7(3) . . . . ?
N31 C34 C33 O34 -124.26(15) . . . . ?
O31 C34 C33 C32 174.0(2) . . . . ?
N31 C34 C33 C32 -5.99(13) . . . . ?
N31 C32 C33 O34 118.36(16) . . . . ?
C44 C32 C33 O34 -119.66(17) . . . . ?
C42 C32 C33 O34 4.5(2) . . . . ?
N31 C32 C33 C34 5.57(12) . . . . ?
C44 C32 C33 C34 127.55(16) . . . . ?
C42 C32 C33 C34 -108.34(15) . . . . ?
C34 C33 O34 C50A -156.6(6) . . . . ?
C32 C33 O34 C50A 106.4(7) . . . . ?
C34 C33 O34 C50B 178.4(7) . . . . ?
C32 C33 O34 C50B 81.4(7) . . . . ?
C50B O34 C50A O35A 90(2) . . . . ?
C33 O34 C50A O35A -3.0(11) . . . . ?
C50B O34 C50A C51A -92(2) . . . . ?
C33 O34 C50A C51A 175.8(5) . . . . ?
C50A O34 C50B O35B -100(2) . . . . ?
C33 O34 C50B O35B -0.7(12) . . . . ?
C50A O34 C50B C51B 84(2) . . . . ?
C33 O34 C50B C51B -177.0(6) . . . . ?
