#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/25/1502599.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_1502599
loop_
_publ_author_name
'Pelletier, Sophie M.-C.'
'Ray, Peter C.'
'Dixon, Darren J.'
_publ_section_title
;
 Diastereoselective synthesis of 1,3,5-trisubstituted
 4-nitropyrrolidin-2-ones via a nitro-Mannich/lactamization cascade.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6406
_journal_page_last               6409
_journal_paper_doi               10.1021/ol202710g
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C21 H23 N3 O5'
_chemical_formula_weight         397.42
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.441(9)
_cell_angle_beta                 102.125(8)
_cell_angle_gamma                105.899(8)
_cell_formula_units_Z            4
_cell_length_a                   9.1434(15)
_cell_length_b                   13.852(2)
_cell_length_c                   16.964(3)
_cell_measurement_reflns_used    9866
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.85
_cell_measurement_theta_min      2.41
_cell_volume                     1999.4(6)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            44298
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.98
_diffrn_reflns_theta_min         1.24
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9775
_exptl_absorpt_correction_T_min  0.9414
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     537
_refine_ls_number_reflns         11312
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0563P)²+0.8588P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1208
_refine_ls_wR_factor_ref         0.1307
_reflns_number_gt                8796
_reflns_number_total             11312
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol202710g_si_001.cif
_cod_data_source_block           2l
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1999.3(6)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1502599
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1A O 0.45688(12) 0.27522(9) 0.11110(6) 0.0289(2) Uani 1 1 d .
C1A C 0.35319(15) 0.28950(10) 0.05881(8) 0.0207(3) Uani 1 1 d .
C2A C 0.28161(16) 0.37649(10) 0.06609(9) 0.0230(3) Uani 1 1 d .
H2A H 0.3633 0.4414 0.0659 0.028 Uiso 1 1 calc R
N3A N 0.1617(2) 0.44849(11) -0.05566(13) 0.0620(6) Uani 1 1 d D
C3A C 0.15300(17) 0.35590(10) -0.01256(9) 0.0246(3) Uani 1 1 d .
H3A H 0.0481 0.3320 0.0001 0.029 Uiso 1 1 calc R
C4A C 0.17525(15) 0.27045(9) -0.07021(8) 0.0173(2) Uani 1 1 d .
H4A H 0.2263 0.3011 -0.1128 0.021 Uiso 1 1 calc R
N5A N 0.28449(13) 0.23137(8) -0.01508(6) 0.0176(2) Uani 1 1 d .
C6A C 0.34266(16) 0.15063(10) -0.04545(8) 0.0208(3) Uani 1 1 d .
H6A1 H 0.2528 0.0895 -0.0691 0.025 Uiso 1 1 calc R
H6A2 H 0.4116 0.1328 0.0007 0.025 Uiso 1 1 calc R
C7A C 0.43408(17) 0.18190(10) -0.11026(8) 0.0225(3) Uani 1 1 d .
H7A1 H 0.4714 0.1251 -0.1282 0.027 Uiso 1 1 calc R
H7A2 H 0.3625 0.1945 -0.1582 0.027 Uiso 1 1 calc R
C8A C 0.57417(17) 0.27654(11) -0.07980(8) 0.0253(3) Uani 1 1 d .
H8A1 H 0.6474 0.2632 -0.0330 0.030 Uiso 1 1 calc R
H8A2 H 0.5373 0.3328 -0.0603 0.030 Uiso 1 1 calc R
C9A C 0.6621(2) 0.30944(12) -0.14522(10) 0.0309(3) Uani 1 1 d .
H9A1 H 0.6989 0.2541 -0.1649 0.046 Uiso 1 1 calc R
H9A2 H 0.7521 0.3694 -0.1220 0.046 Uiso 1 1 calc R
H9A3 H 0.5917 0.3259 -0.1907 0.046 Uiso 1 1 calc R
C10A C 0.22526(17) 0.38472(11) 0.14572(9) 0.0257(3) Uani 1 1 d .
H10A H 0.3145 0.3925 0.1928 0.031 Uiso 1 1 calc R
H10B H 0.1912 0.4465 0.1501 0.031 Uiso 1 1 calc R
C11A C 0.09148(16) 0.29370(10) 0.15028(8) 0.0204(3) Uani 1 1 d .
C12A C -0.06303(16) 0.29836(10) 0.13336(8) 0.0210(3) Uani 1 1 d .
H12A H -0.0833 0.3595 0.1198 0.025 Uiso 1 1 calc R
C13A C -0.18758(16) 0.21473(10) 0.13602(8) 0.0207(3) Uani 1 1 d .
H13A H -0.2916 0.2191 0.1246 0.025 Uiso 1 1 calc R
C14A C -0.15840(17) 0.12471(10) 0.15561(8) 0.0228(3) Uani 1 1 d .
H14A H -0.2428 0.0673 0.1571 0.027 Uiso 1 1 calc R
C15A C -0.00508(18) 0.11896(11) 0.17302(9) 0.0255(3) Uani 1 1 d .
H15A H 0.0147 0.0577 0.1866 0.031 Uiso 1 1 calc R
C16A C 0.11893(17) 0.20260(11) 0.17055(8) 0.0230(3) Uani 1 1 d .
H16A H 0.2229 0.1981 0.1827 0.028 Uiso 1 1 calc R
C17A C 0.02297(14) 0.18915(9) -0.11111(7) 0.0160(2) Uani 1 1 d .
C18A C -0.02758(15) 0.17186(10) -0.19601(7) 0.0179(2) Uani 1 1 d .
H18A H 0.0366 0.2083 -0.2278 0.022 Uiso 1 1 calc R
C19A C -0.17132(16) 0.10161(10) -0.23449(8) 0.0207(3) Uani 1 1 d .
H19A H -0.2067 0.0897 -0.2922 0.025 Uiso 1 1 calc R
N20A N -0.41753(15) -0.02004(9) -0.22618(9) 0.0308(3) Uani 1 1 d .
C20A C -0.26127(15) 0.04959(10) -0.18589(8) 0.0205(3) Uani 1 1 d .
O21A O -0.47371(14) -0.01358(10) -0.29787(8) 0.0448(3) Uani 1 1 d .
C21A C -0.21226(16) 0.06195(10) -0.10141(9) 0.0224(3) Uani 1 1 d .
H21A H -0.2751 0.0231 -0.0702 0.027 Uiso 1 1 calc R
O22A O -0.48556(14) -0.07959(9) -0.18663(9) 0.0473(3) Uani 1 1 d .
C22A C -0.06888(16) 0.13258(10) -0.06384(8) 0.0199(3) Uani 1 1 d .
H22A H -0.0328 0.1427 -0.0062 0.024 Uiso 1 1 calc R
O31A O 0.0674(2) 0.43739(17) -0.12705(14) 0.0470(7) Uani 0.604(3) 1 d PD
O32A O 0.0473(4) 0.4857(3) -0.0368(3) 0.0811(15) Uani 0.511(4) 1 d PD
O33A O 0.2848(2) 0.50834(14) -0.05517(10) 0.0609(6) Uani 0.885(4) 1 d PD
O1B O 0.11974(13) 0.80758(8) 0.39102(6) 0.0288(2) Uani 1 1 d .
C1B C 0.21740(16) 0.79585(10) 0.44809(8) 0.0200(3) Uani 1 1 d .
C2B C 0.38935(16) 0.80961(10) 0.44928(8) 0.0201(3) Uani 1 1 d .
H2B H 0.4430 0.8836 0.4521 0.024 Uiso 1 1 calc R
N3B N 0.60793(14) 0.84773(10) 0.57983(8) 0.0284(3) Uani 1 1 d .
C3B C 0.45415(15) 0.77573(10) 0.52960(8) 0.0190(2) Uani 1 1 d .
H3B H 0.4693 0.7078 0.5173 0.023 Uiso 1 1 calc R
C4B C 0.32779(14) 0.76426(9) 0.58060(7) 0.0154(2) Uani 1 1 d .
H4B H 0.3611 0.8231 0.6252 0.019 Uiso 1 1 calc R
N5B N 0.19049(13) 0.76951(8) 0.52072(6) 0.0171(2) Uani 1 1 d .
C6B C 0.04479(15) 0.76779(10) 0.54477(8) 0.0200(3) Uani 1 1 d .
H6B1 H 0.0026 0.7019 0.5631 0.024 Uiso 1 1 calc R
H6B2 H -0.0337 0.7737 0.4968 0.024 Uiso 1 1 calc R
C7B C 0.06928(16) 0.85394(10) 0.61330(8) 0.0219(3) Uani 1 1 d .
H7B1 H -0.0329 0.8512 0.6255 0.026 Uiso 1 1 calc R
H7B2 H 0.1387 0.8436 0.6631 0.026 Uiso 1 1 calc R
C8B C 0.14133(19) 0.95876(11) 0.59167(9) 0.0279(3) Uani 1 1 d .
H8B1 H 0.0782 0.9665 0.5388 0.033 Uiso 1 1 calc R
H8B2 H 0.2485 0.9644 0.5855 0.033 Uiso 1 1 calc R
C9B C 0.1488(2) 1.04413(13) 0.65678(13) 0.0459(5) Uani 1 1 d .
H9B1 H 0.0430 1.0384 0.6636 0.069 Uiso 1 1 calc R
H9B2 H 0.1925 1.1099 0.6399 0.069 Uiso 1 1 calc R
H9B3 H 0.2156 1.0388 0.7086 0.069 Uiso 1 1 calc R
C10B C 0.41057(18) 0.75237(11) 0.37230(8) 0.0240(3) Uani 1 1 d .
H10C H 0.3612 0.7773 0.3235 0.029 Uiso 1 1 calc R
H10D H 0.5239 0.7682 0.3746 0.029 Uiso 1 1 calc R
C11B C 0.34024(17) 0.63824(11) 0.36314(8) 0.0216(3) Uani 1 1 d .
C12B C 0.43315(17) 0.57694(11) 0.39232(8) 0.0241(3) Uani 1 1 d .
H12B H 0.5411 0.6076 0.4175 0.029 Uiso 1 1 calc R
C13B C 0.37007(18) 0.47179(11) 0.38514(9) 0.0267(3) Uani 1 1 d .
H13B H 0.4348 0.4316 0.4053 0.032 Uiso 1 1 calc R
C14B C 0.21211(19) 0.42614(11) 0.34840(9) 0.0283(3) Uani 1 1 d .
H14B H 0.1686 0.3546 0.3432 0.034 Uiso 1 1 calc R
C15B C 0.11780(18) 0.48605(12) 0.31924(9) 0.0300(3) Uani 1 1 d .
H15B H 0.0098 0.4551 0.2944 0.036 Uiso 1 1 calc R
C16B C 0.18132(18) 0.59110(12) 0.32640(8) 0.0267(3) Uani 1 1 d .
H16B H 0.1161 0.6310 0.3062 0.032 Uiso 1 1 calc R
C17B C 0.29876(14) 0.66551(9) 0.61677(7) 0.0156(2) Uani 1 1 d .
C18B C 0.35101(15) 0.66754(10) 0.70058(8) 0.0184(2) Uani 1 1 d .
H18B H 0.3958 0.7307 0.7353 0.022 Uiso 1 1 calc R
C19B C 0.33770(16) 0.57698(11) 0.73368(8) 0.0220(3) Uani 1 1 d .
H19B H 0.3726 0.5776 0.7906 0.026 Uiso 1 1 calc R
N20B N 0.27140(16) 0.39078(10) 0.71446(10) 0.0352(3) Uani 1 1 d .
C20B C 0.27215(16) 0.48640(10) 0.68109(9) 0.0232(3) Uani 1 1 d .
O21B O 0.22993(17) 0.31181(9) 0.66699(11) 0.0602(4) Uani 1 1 d .
C21B C 0.21279(16) 0.48170(10) 0.59791(9) 0.0239(3) Uani 1 1 d .
H21B H 0.1645 0.4182 0.5639 0.029 Uiso 1 1 calc R
O22B O 0.3210(2) 0.39619(12) 0.78877(9) 0.0670(5) Uani 1 1 d .
C22B C 0.22579(15) 0.57228(10) 0.56568(8) 0.0203(3) Uani 1 1 d .
H22B H 0.1853 0.5711 0.5091 0.024 Uiso 1 1 calc R
O31B O 0.66422(17) 0.92884(11) 0.55801(9) 0.0593(4) Uani 1 1 d .
O32B O 0.66674(13) 0.82015(10) 0.64267(8) 0.0420(3) Uani 1 1 d .
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_3
O1A C1A N5A 125.61(12) .
O1A C1A C2A 125.24(12) .
N5A C1A C2A 109.15(11) .
C1A C2A C3A 104.16(10) .
C1A C2A C10A 112.41(12) .
C3A C2A C10A 114.96(12) .
O33A N3A O31A 108.7(2) .
O33A N3A O32A 117.7(2) .
O31A N3A O32A 78.4(2) .
O33A N3A C3A 121.59(16) .
O31A N3A C3A 117.96(16) .
O32A N3A C3A 104.8(2) .
N3A C3A C2A 112.64(12) .
N3A C3A C4A 108.59(13) .
C2A C3A C4A 107.28(11) .
N5A C4A C17A 112.66(10) .
N5A C4A C3A 102.45(10) .
C17A C4A C3A 113.24(11) .
C1A N5A C4A 115.07(10) .
C1A N5A C6A 122.39(11) .
C4A N5A C6A 120.86(10) .
N5A C6A C7A 112.33(11) .
C8A C7A C6A 113.09(11) .
C7A C8A C9A 113.00(12) .
C11A C10A C2A 113.50(11) .
C12A C11A C16A 118.48(12) .
C12A C11A C10A 120.49(12) .
C16A C11A C10A 121.03(12) .
C13A C12A C11A 121.14(12) .
C14A C13A C12A 119.63(13) .
C13A C14A C15A 119.94(13) .
C16A C15A C14A 120.29(13) .
C15A C16A C11A 120.51(13) .
C18A C17A C22A 119.96(12) .
C18A C17A C4A 119.74(11) .
C22A C17A C4A 120.29(11) .
C19A C18A C17A 120.57(12) .
C20A C19A C18A 117.92(12) .
O22A N20A O21A 123.70(14) .
O22A N20A C20A 118.37(14) .
O21A N20A C20A 117.92(13) .
C19A C20A C21A 123.15(12) .
C19A C20A N20A 117.98(13) .
C21A C20A N20A 118.86(13) .
C22A C21A C20A 118.26(12) .
C21A C22A C17A 120.07(12) .
N3A O31A O32A 52.55(17) .
N3A O32A O31A 49.01(17) .
N3A O32A O32A 147.9(4) 2_565
O31A O32A O32A 158.2(4) 2_565
O1B C1B N5B 125.59(13) .
O1B C1B C2B 125.20(12) .
N5B C1B C2B 109.21(11) .
C1B C2B C3B 104.10(10) .
C1B C2B C10B 112.62(11) .
C3B C2B C10B 114.82(11) .
O31B N3B O32B 123.89(14) .
O31B N3B C3B 120.07(12) .
O32B N3B C3B 116.02(12) .
N3B C3B C2B 114.54(11) .
N3B C3B C4B 109.05(10) .
C2B C3B C4B 107.44(10) .
N5B C4B C17B 112.74(10) .
N5B C4B C3B 102.42(9) .
C17B C4B C3B 112.37(10) .
C1B N5B C4B 115.33(11) .
C1B N5B C6B 122.80(11) .
C4B N5B C6B 120.63(10) .
N5B C6B C7B 112.31(11) .
C8B C7B C6B 112.80(11) .
C7B C8B C9B 112.03(14) .
C11B C10B C2B 113.48(11) .
C16B C11B C12B 118.15(13) .
C16B C11B C10B 121.29(13) .
C12B C11B C10B 120.55(13) .
C13B C12B C11B 121.36(14) .
C14B C13B C12B 119.78(14) .
C13B C14B C15B 119.62(14) .
C16B C15B C14B 120.44(14) .
C15B C16B C11B 120.65(14) .
C18B C17B C22B 120.04(11) .
C18B C17B C4B 119.74(11) .
C22B C17B C4B 120.16(11) .
C17B C18B C19B 120.33(12) .
C20B C19B C18B 118.12(12) .
O21B N20B O22B 123.61(14) .
O21B N20B C20B 118.55(15) .
O22B N20B C20B 117.71(15) .
C19B C20B C21B 122.94(12) .
C19B C20B N20B 118.39(13) .
C21B C20B N20B 118.61(13) .
C20B C21B C22B 118.40(12) .
C21B C22B C17B 120.04(12) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1A C1A 1.2253(16) .
C1A N5A 1.3600(17) .
C1A C2A 1.5292(19) .
C2A C3A 1.531(2) .
C2A C10A 1.551(2) .
N3A O33A 1.199(2) .
N3A O31A 1.302(3) .
N3A O32A 1.369(4) .
N3A C3A 1.516(2) .
C3A C4A 1.5604(18) .
C4A N5A 1.4655(16) .
C4A C17A 1.5173(18) .
N5A C6A 1.4666(16) .
C6A C7A 1.5351(19) .
C7A C8A 1.524(2) .
C8A C9A 1.529(2) .
C10A C11A 1.5171(19) .
C11A C12A 1.4018(19) .
C11A C16A 1.4063(19) .
C12A C13A 1.3956(19) .
C13A C14A 1.3948(19) .
C14A C15A 1.396(2) .
C15A C16A 1.392(2) .
C17A C18A 1.3971(17) .
C17A C22A 1.4078(17) .
C18A C19A 1.3931(19) .
C19A C20A 1.3884(19) .
N20A O22A 1.2237(19) .
N20A O21A 1.2372(19) .
N20A C20A 1.4736(18) .
C20A C21A 1.391(2) .
C21A C22A 1.3899(19) .
O31A O32A 1.689(5) .
O32A O32A 1.739(8) 2_565
O1B C1B 1.2255(16) .
C1B N5B 1.3636(16) .
C1B C2B 1.5266(19) .
C2B C3B 1.5296(17) .
C2B C10B 1.5499(18) .
N3B O31B 1.2213(18) .
N3B O32B 1.2274(17) .
N3B C3B 1.5148(19) .
C3B C4B 1.5651(17) .
C4B N5B 1.4626(16) .
C4B C17B 1.5223(17) .
N5B C6B 1.4677(17) .
C6B C7B 1.5345(18) .
C7B C8B 1.529(2) .
C8B C9B 1.531(2) .
C10B C11B 1.516(2) .
C11B C16B 1.401(2) .
C11B C12B 1.4041(19) .
C12B C13B 1.397(2) .
C13B C14B 1.391(2) .
C14B C15B 1.398(2) .
C15B C16B 1.396(2) .
C17B C18B 1.3969(17) .
C17B C22B 1.4056(17) .
C18B C19B 1.3993(18) .
C19B C20B 1.385(2) .
N20B O21B 1.223(2) .
N20B O22B 1.236(2) .
N20B C20B 1.4792(17) .
C20B C21B 1.391(2) .
C21B C22B 1.3925(19) .
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_4
O1A C1A C2A C3A -176.87(14) .
N5A C1A C2A C3A 3.70(14) .
O1A C1A C2A C10A -51.78(18) .
N5A C1A C2A C10A 128.79(12) .
O33A N3A C3A C2A 34.9(3) .
O31A N3A C3A C2A 173.68(19) .
O32A N3A C3A C2A -101.7(2) .
O33A N3A C3A C4A -83.7(2) .
O31A N3A C3A C4A 55.0(2) .
O32A N3A C3A C4A 139.6(2) .
C1A C2A C3A N3A -130.27(14) .
C10A C2A C3A N3A 106.28(16) .
C1A C2A C3A C4A -10.83(14) .
C10A C2A C3A C4A -134.28(12) .
N3A C3A C4A N5A 135.64(12) .
C2A C3A C4A N5A 13.64(13) .
N3A C3A C4A C17A -102.74(14) .
C2A C3A C4A C17A 135.26(11) .
O1A C1A N5A C4A -173.74(13) .
C2A C1A N5A C4A 5.69(15) .
O1A C1A N5A C6A -8.4(2) .
C2A C1A N5A C6A 171.03(11) .
C17A C4A N5A C1A -134.20(11) .
C3A C4A N5A C1A -12.19(14) .
C17A C4A N5A C6A 60.22(15) .
C3A C4A N5A C6A -177.77(11) .
C1A N5A C6A C7A -103.72(14) .
C4A N5A C6A C7A 60.79(15) .
N5A C6A C7A C8A 58.11(15) .
C6A C7A C8A C9A -178.23(12) .
C1A C2A C10A C11A -64.82(16) .
C3A C2A C10A C11A 54.11(16) .
C2A C10A C11A C12A -100.96(15) .
C2A C10A C11A C16A 78.29(17) .
C16A C11A C12A C13A -0.31(19) .
C10A C11A C12A C13A 178.95(12) .
C11A C12A C13A C14A -0.2(2) .
C12A C13A C14A C15A 0.5(2) .
C13A C14A C15A C16A -0.3(2) .
C14A C15A C16A C11A -0.2(2) .
C12A C11A C16A C15A 0.51(19) .
C10A C11A C16A C15A -178.75(12) .
N5A C4A C17A C18A -125.00(12) .
C3A C4A C17A C18A 119.30(13) .
N5A C4A C17A C22A 56.25(15) .
C3A C4A C17A C22A -59.44(15) .
C22A C17A C18A C19A 2.41(18) .
C4A C17A C18A C19A -176.34(11) .
C17A C18A C19A C20A -0.28(18) .
C18A C19A C20A C21A -2.22(19) .
C18A C19A C20A N20A 176.27(11) .
O22A N20A C20A C19A 166.84(13) .
O21A N20A C20A C19A -14.46(18) .
O22A N20A C20A C21A -14.60(19) .
O21A N20A C20A C21A 164.11(13) .
C19A C20A C21A C22A 2.5(2) .
N20A C20A C21A C22A -176.00(12) .
C20A C21A C22A C17A -0.24(19) .
C18A C17A C22A C21A -2.15(19) .
C4A C17A C22A C21A 176.60(12) .
O33A N3A O31A O32A -115.6(2) .
C3A N3A O31A O32A 100.8(3) .
O33A N3A O32A O31A 105.2(2) .
C3A N3A O32A O31A -116.16(17) .
O33A N3A O32A O32A -96.5(7) 2_565
O31A N3A O32A O32A 158.4(8) 2_565
C3A N3A O32A O32A 42.2(8) 2_565
N3A O31A O32A O32A -148.2(8) 2_565
O1B C1B C2B C3B -174.41(13) .
N5B C1B C2B C3B 6.17(14) .
O1B C1B C2B C10B -49.41(18) .
N5B C1B C2B C10B 131.18(11) .
O31B N3B C3B C2B 5.2(2) .
O32B N3B C3B C2B -176.53(12) .
O31B N3B C3B C4B -115.21(16) .
O32B N3B C3B C4B 63.07(16) .
C1B C2B C3B N3B -132.54(11) .
C10B C2B C3B N3B 103.88(14) .
C1B C2B C3B C4B -11.25(13) .
C10B C2B C3B C4B -134.83(12) .
N3B C3B C4B N5B 136.74(10) .
C2B C3B C4B N5B 12.07(12) .
N3B C3B C4B C17B -102.02(12) .
C2B C3B C4B C17B 133.31(11) .
O1B C1B N5B C4B -177.56(12) .
C2B C1B N5B C4B 1.85(15) .
O1B C1B N5B C6B -10.3(2) .
C2B C1B N5B C6B 169.14(11) .
C17B C4B N5B C1B -129.75(11) .
C3B C4B N5B C1B -8.77(13) .
C17B C4B N5B C6B 62.66(14) .
C3B C4B N5B C6B -176.35(10) .
C1B N5B C6B C7B -109.21(14) .
C4B N5B C6B C7B 57.42(15) .
N5B C6B C7B C8B 56.25(15) .
C6B C7B C8B C9B 173.93(13) .
C1B C2B C10B C11B -62.76(15) .
C3B C2B C10B C11B 56.15(16) .
C2B C10B C11B C16B 84.67(16) .
C2B C10B C11B C12B -94.61(15) .
C16B C11B C12B C13B 0.07(19) .
C10B C11B C12B C13B 179.37(12) .
C11B C12B C13B C14B 0.0(2) .
C12B C13B C14B C15B -0.2(2) .
C13B C14B C15B C16B 0.3(2) .
C14B C15B C16B C11B -0.2(2) .
C12B C11B C16B C15B 0.04(19) .
C10B C11B C16B C15B -179.25(12) .
N5B C4B C17B C18B -136.11(12) .
C3B C4B C17B C18B 108.76(13) .
N5B C4B C17B C22B 46.66(15) .
C3B C4B C17B C22B -68.47(15) .
C22B C17B C18B C19B 2.97(19) .
C4B C17B C18B C19B -174.26(11) .
C17B C18B C19B C20B 0.18(19) .
C18B C19B C20B C21B -3.1(2) .
C18B C19B C20B N20B 174.29(12) .
O21B N20B C20B C19B -171.91(14) .
O22B N20B C20B C19B 4.3(2) .
O21B N20B C20B C21B 5.6(2) .
O22B N20B C20B C21B -178.25(15) .
C19B C20B C21B C22B 2.7(2) .
N20B C20B C21B C22B -174.65(12) .
C20B C21B C22B C17B 0.6(2) .
C18B C17B C22B C21B -3.3(2) .
C4B C17B C22B C21B 173.88(12) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139037542
