#------------------------------------------------------------------------------
#$Date: 2023-06-05 06:43:33 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284196 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/15/7131575.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_7131575
loop_
_publ_author_name
'Mo, Nan-Nan'
'Miao, Yu-Hang'
'Xiao, Xiao'
'Hua, Yuan-Zhao'
'Wang, Min-Can'
'Huang, Lihua'
'Mei, Guang-Jian'
_publ_section_title
;
 Catalytic asymmetric de novo construction of 4-pyrrolin-2-ones
 via intermolecular formal [3+2] cycloaddition of azoalkenes with
 azlactones.
;
_journal_issue                   39
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5902
_journal_page_last               5905
_journal_paper_doi               10.1039/d3cc01194a
_journal_volume                  59
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H23 N3 O8'
_chemical_formula_sum            'C20 H23 N3 O8'
_chemical_formula_weight         433.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-02-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-03-07 deposited with the CCDC.	2023-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.027(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.0745(7)
_cell_length_b                   12.0391(4)
_cell_length_c                   9.3014(3)
_cell_measurement_reflns_used    4651
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4080
_cell_measurement_theta_min      4.2740
_cell_volume                     2256.49(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  16.00   1.00    1.00    --    0.00 -57.00-180.00   32
  2  ω   -106.00 -80.00   1.00    3.00    --  -33.50 -19.00 -90.00   26
  3  ω    -31.00  10.00   1.00    3.00    --  -33.50  37.00 -90.00   41
  4  ω    -59.00 -25.00   1.00    3.00    --  -33.50 -19.00 -90.00   34
  5  ω    -71.00 -45.00   1.00    3.00    --  -33.50 178.00-120.00   26
  6  ω   -108.00 -82.00   1.00    3.00    --  -33.50 178.00-120.00   26
  7  ω     59.00  91.00   1.00    3.00    --   36.47 178.00-120.00   32
  8  ω     59.00 110.00   1.00    3.00    --   36.47 178.00-150.00   51
  9  ω     33.00  74.00   1.00    3.00    --   36.47  57.00  30.00   41
 10  ω     -3.00  22.00   1.00    3.00    --   36.47 100.00-136.80   25
 11  ω      9.00  49.00   1.00    3.00    --   36.47  77.00  30.00   40
 12  ω     21.00  47.00   1.00    3.00    --   36.47  37.00  30.00   26
 13  ω     12.00  47.00   1.00    3.00    --   36.47  77.00 -30.00   35
 14  ω     57.00 107.00   1.00    3.00    --   36.47 178.00   0.00   50
 15  ω     29.00  68.00   1.00    3.00    --   36.47  57.00 -60.00   39
 16  ω     49.00  94.00   1.00    3.00    --   36.47  57.00 120.00   45
 17  ω     54.00 105.00   1.00    3.00    --   36.47  77.00  30.00   51
 18  ω     -3.00  23.00   1.00    3.00    --   36.47 -99.00  30.00   26
 19  ω     80.00 105.00   1.00    3.00    --   36.47  57.00 -60.00   25
 20  ω     23.00  77.00   1.00    3.00    --   36.47 -99.00-180.00   54
 21  ω      1.00  40.00   1.00    3.00    --   36.47  19.00 -60.00   39
 22  ω     50.00  76.00   1.00    3.00    --   36.47  57.00  60.00   26
 23  ω     20.00  46.00   1.00    3.00    --   36.47  77.00 -60.00   26
 24  ω      1.00  27.00   1.00    3.00    --   36.47  95.00 -61.91   26
 25  ω     -8.00  17.00   1.00    3.00    --   36.47 106.00  93.56   25
 26  ω      0.00  76.00   1.00    3.00    --   36.47  19.00  60.00   76
 27  ω     68.00 104.00   1.00    3.00    --   36.47  57.00 -90.00   36
 28  ω     40.00  66.00   1.00    3.00    --   36.47  57.00-180.00   26
 29  ω     18.00  46.00   1.00    3.00    --   36.47  57.00  60.00   28
 30  ω     80.00 160.00   1.00   13.00    --  108.00  77.00-180.00   80
 31  ω     82.00 108.00   1.00   13.00    --  108.00  30.00  30.00   26
 32  ω     79.00 105.00   1.00   13.00    --  108.00  77.00   0.00   26
 33  ω     82.00 110.00   1.00   13.00    --  108.00  30.00  60.00   28
 34  ω     84.00 110.00   1.00   13.00    --  108.00  30.00  90.00   26
 35  ω    117.00 176.00   1.00   13.00    --  108.00  77.00  60.00   59
 36  ω     79.00 106.00   1.00   13.00    --  108.00  77.00  60.00   27
 37  ω     37.00 108.00   1.00   13.00    --  108.00-111.00  90.00   71
 38  ω     88.00 114.00   1.00   13.00    --  108.00  45.00  90.00   26
 39  ω    137.00 163.00   1.00   13.00    --  108.00  61.00   0.00   26
 40  ω    144.00 170.00   1.00   13.00    --  108.00  77.00  90.00   26
 41  ω     79.00 105.00   1.00   13.00    --  108.00  77.00  90.00   26
 42  ω     82.00 108.00   1.00   13.00    --  108.00  30.00 150.00   26
 43  ω    110.00 176.00   1.00   13.00    --  108.00  77.00 150.00   66
 44  ω     79.00 105.00   1.00   13.00    --  108.00  77.00 150.00   26
 45  ω    111.00 176.00   1.00   13.00    --  108.00  77.00  30.00   65
 46  ω     41.00 121.00   1.00   13.00    --  108.00 -61.00  60.00   80
 47  ω     88.00 114.00   1.00   13.00    --  108.00  45.00  60.00   26
 48  ω     79.00 105.00   1.00   13.00    --  108.00  77.00  30.00   26
 49  ω     88.00 114.00   1.00   13.00    --  108.00  61.00  60.00   26
 50  ω     79.00 105.00   1.00   13.00    --  108.00  77.00 120.00   26
 51  ω     88.00 114.00   1.00   13.00    --  108.00  45.00 120.00   26
 52  ω     80.00 155.00   1.00   13.00    --  108.00  77.00 -60.00   75
 53  ω     88.00 119.00   1.00   13.00    --  108.00  61.00  30.00   31
 54  ω     84.00 169.00   1.00   13.00    --  108.00  30.00 120.00   85
 55  ω     88.00 114.00   1.00   13.00    --  108.00  61.00 120.00   26
 56  ω     91.00 117.00   1.00   13.00    --  108.00  61.00 -30.00   26
 57  ω     93.00 144.00   1.00   13.00    --  108.00  45.00 -30.00   51
 58  ω     84.00 110.00   1.00   13.00    --  108.00  30.00   0.00   26
 59  ω     88.00 114.00   1.00   13.00    --  108.00  61.00  90.00   26
 60  ω     79.00 104.00   1.00   13.00    --  108.00  77.00 -30.00   25
 61  ω     88.00 114.00   1.00   13.00    --  108.00  61.00   0.00   26
 62  ω     70.00 109.00   1.00   13.00    --  108.00 -94.00 150.00   39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0478029582
_diffrn_orient_matrix_UB_12      -0.0061207369
_diffrn_orient_matrix_UB_13      -0.1607290851
_diffrn_orient_matrix_UB_21      0.0595205248
_diffrn_orient_matrix_UB_22      -0.0142437450
_diffrn_orient_matrix_UB_23      -0.0628819169
_diffrn_orient_matrix_UB_31      -0.0043670009
_diffrn_orient_matrix_UB_32      -0.1269871787
_diffrn_orient_matrix_UB_33      0.0147813204
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11094
_diffrn_reflns_point_group_measured_fraction_full 0.889
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.853
_diffrn_reflns_theta_min         4.278
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.845
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1284 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         3802
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0403
_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)+(0.0693P)²+0.2933P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1161
_reflns_Friedel_coverage         0.674
_reflns_Friedel_fraction_full    0.766
_reflns_Friedel_fraction_max     0.739
_reflns_number_gt                3483
_reflns_number_total             3802
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc01194a2.cif
_cod_data_source_block           20230221a
_cod_depositor_comments          'Adding full bibliography for 7131575.cif.'
_cod_original_cell_volume        2256.50(14)
_cod_database_code               7131575
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3N2O2
_chemical_oxdiff_usercomment     r
_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   0.920
_shelx_estimated_absorpt_t_min   0.870
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Restrained distances
 N3-H3
 0.87 with sigma of 0.02
 C7A-C6
 1.54 with sigma of 0.02
 C14-C15
 1.6 with sigma of 0.02
 C19-C20
 1.6 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C12) = Uanis(C12A)
Uanis(C11) = Uanis(C11A)
Uanis(C10) = Uanis(C10A)
Uanis(C9) = Uanis(C9A)
Uanis(C8) = Uanis(C8A)
Uanis(C7) = Uanis(C7A)
4. Others
 Sof(C12A)=Sof(H12A)=Sof(C11A)=Sof(H11A)=Sof(C10A)=Sof(H10A)=Sof(C9A)=Sof(H9A)=
 Sof(C8A)=Sof(H8A)=1-FVAR(1)
 Sof(C12)=Sof(H12)=Sof(C11)=Sof(H11)=Sof(C10)=Sof(H10)=Sof(C9)=Sof(H9)=Sof(C8)=
 Sof(H8)=FVAR(1)
 Sof(C7A)=1-FVAR(2)
 Sof(C7)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C19(H19A,H19B)
5.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C10(H10), C9(H9), C8(H8), C12A(H12A), C11A(H11A),
 C10A(H10A), C9A(H9A), C8A(H8A)
5.c Fitted hexagon refined as free rotating group:
 C12(C11,C10,C9,C8,C7), C7A(C12A,C11A,C10A,C9A,C8A)
5.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.278
_oxdiff_exptl_absorpt_empirical_full_min 0.888
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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 0.74115(15) 0.2363(3) 0.2336(3) 0.0548(7) Uani 1 1 d . . . . .
C2 C 0.70638(13) 0.1646(2) 0.0938(3) 0.0503(6) Uani 1 1 d . . . . .
C3 C 0.75822(13) 0.1631(2) 0.0105(3) 0.0479(6) Uani 1 1 d . . . . .
C4 C 0.81282(13) 0.2190(3) 0.0877(3) 0.0503(6) Uani 1 1 d . . . . .
C5 C 0.87637(15) 0.2435(3) 0.0562(4) 0.0683(9) Uani 1 1 d . . . . .
H5A H 0.8788 0.2018 -0.0301 0.102 Uiso 1 1 calc GR . . . .
H5B H 0.9127 0.2230 0.1416 0.102 Uiso 1 1 calc GR . . . .
H5C H 0.8788 0.3214 0.0367 0.102 Uiso 1 1 calc GR . . . .
C6 C 0.63847(14) 0.3217(3) -0.0219(3) 0.0559(7) Uani 1 1 d D . . . .
C12 C 0.57632(19) 0.4695(4) -0.1913(7) 0.0844(17) Uani 0.662(5) 1 d . . P A 1
H12 H 0.6158 0.5095 -0.1653 0.101 Uiso 0.662(5) 1 calc R . P A 1
C11 C 0.5199(2) 0.5138(4) -0.2929(6) 0.112(3) Uani 0.662(5) 1 d G . P A 1
H11 H 0.5216 0.5834 -0.3348 0.134 Uiso 0.662(5) 1 calc R . P A 1
C10 C 0.4609(2) 0.4539(5) -0.3318(6) 0.101(2) Uani 0.662(5) 1 d G . P A 1
H10 H 0.4232 0.4836 -0.3998 0.122 Uiso 0.662(5) 1 calc R . P A 1
C9 C 0.4583(2) 0.3498(5) -0.2692(7) 0.119(3) Uani 0.662(5) 1 d G . P A 1
H9 H 0.4189 0.3098 -0.2952 0.143 Uiso 0.662(5) 1 calc R . P A 1
C8 C 0.5147(3) 0.3056(4) -0.1676(7) 0.082(2) Uani 0.662(5) 1 d G . P A 1
H8 H 0.5130 0.2359 -0.1257 0.099 Uiso 0.662(5) 1 calc R . P A 1
C7 C 0.5737(2) 0.3654(4) -0.1287(6) 0.0640(11) Uani 0.70(3) 1 d G . P A 1
C13 C 0.69271(15) 0.0488(3) 0.1465(3) 0.0560(7) Uani 1 1 d . . . . .
C14 C 0.7425(2) -0.1052(3) 0.2912(4) 0.0764(10) Uani 1 1 d D . . . .
H14A H 0.7205 -0.1541 0.2088 0.092 Uiso 1 1 calc R . . . .
H14B H 0.7167 -0.1036 0.3622 0.092 Uiso 1 1 calc R . . . .
C15 C 0.8107(2) -0.1459(4) 0.3662(4) 0.0823(11) Uani 1 1 d D . . . .
H15A H 0.8320 -0.0970 0.4476 0.123 Uiso 1 1 calc GR . . . .
H15B H 0.8356 -0.1476 0.2949 0.123 Uiso 1 1 calc GR . . . .
H15C H 0.8085 -0.2193 0.4047 0.123 Uiso 1 1 calc GR . . . .
C16 C 0.74410(14) 0.1035(2) -0.1324(3) 0.0504(6) Uani 1 1 d . . . . .
C17 C 0.7768(3) 0.0627(4) -0.3483(4) 0.0829(12) Uani 1 1 d . . . . .
H17A H 0.7853 -0.0152 -0.3298 0.124 Uiso 1 1 calc GR . . . .
H17B H 0.8057 0.0915 -0.4021 0.124 Uiso 1 1 calc GR . . . .
H17C H 0.7315 0.0733 -0.4071 0.124 Uiso 1 1 calc GR . . . .
C18 C 0.88268(14) 0.3020(3) 0.4516(3) 0.0543(7) Uani 1 1 d . . . . .
C19 C 0.9563(2) 0.3720(5) 0.6758(4) 0.0877(13) Uani 1 1 d D . . . .
H19A H 0.9891 0.3169 0.6702 0.105 Uiso 1 1 calc R . . . .
H19B H 0.9323 0.3446 0.7430 0.105 Uiso 1 1 calc R . . . .
C20 C 0.9894(2) 0.4791(5) 0.7326(6) 0.112(2) Uani 1 1 d D . . . .
H20A H 1.0201 0.4682 0.8305 0.169 Uiso 1 1 calc GR . . . .
H20B H 0.9566 0.5327 0.7388 0.169 Uiso 1 1 calc GR . . . .
H20C H 1.0128 0.5056 0.6650 0.169 Uiso 1 1 calc GR . . . .
N1 N 0.80362(12) 0.2588(2) 0.2212(3) 0.0559(6) Uani 1 1 d . . . . .
N2 N 0.84558(14) 0.3350(2) 0.3126(3) 0.0631(7) Uani 1 1 d . . . . .
H2 H 0.835(2) 0.405(5) 0.299(5) 0.090(14) Uiso 1 1 d . . . . .
N3 N 0.64342(12) 0.2128(2) 0.0110(3) 0.0569(6) Uani 1 1 d D . . . .
H3 H 0.6114(14) 0.170(3) -0.028(4) 0.056(9) Uiso 1 1 d D . . . .
O1 O 0.71990(13) 0.2634(2) 0.3338(3) 0.0735(7) Uani 1 1 d . . . . .
O2 O 0.68545(11) 0.3846(2) 0.0263(3) 0.0683(6) Uani 1 1 d . . . . .
O3 O 0.63894(12) 0.0069(2) 0.1103(3) 0.0803(7) Uani 1 1 d . . . . .
O4 O 0.74753(11) 0.0058(2) 0.2349(3) 0.0645(6) Uani 1 1 d . . . . .
O5 O 0.69528(11) 0.0472(2) -0.1796(2) 0.0618(5) Uani 1 1 d . . . . .
O6 O 0.78880(12) 0.1209(2) -0.2058(2) 0.0658(6) Uani 1 1 d . . . . .
O7 O 0.89112(14) 0.2083(2) 0.4951(3) 0.0797(7) Uani 1 1 d . . . . .
O8 O 0.91097(11) 0.3920(2) 0.5280(2) 0.0676(6) Uani 1 1 d . . . . .
C7A C 0.5721(5) 0.3559(9) -0.1063(16) 0.0640(11) Uani 0.30(3) 1 d D . P A 2
C12A C 0.5545(4) 0.4656(8) -0.0920(13) 0.0844(17) Uani 0.338(5) 1 d G . P A 2
H12A H 0.5846 0.5137 -0.0288 0.101 Uiso 0.338(5) 1 calc R . P A 2
C11A C 0.4918(5) 0.5036(8) -0.1720(14) 0.112(3) Uani 0.338(5) 1 d G . P A 2
H11A H 0.4800 0.5771 -0.1623 0.134 Uiso 0.338(5) 1 calc R . P A 2
C10A C 0.4467(4) 0.4318(11) -0.2664(13) 0.101(2) Uani 0.338(5) 1 d G . P A 2
H10A H 0.4048 0.4572 -0.3199 0.122 Uiso 0.338(5) 1 calc R . P A 2
C9A C 0.4643(6) 0.3220(10) -0.2808(14) 0.119(3) Uani 0.338(5) 1 d G . P A 2
H9A H 0.4342 0.2739 -0.3439 0.143 Uiso 0.338(5) 1 calc R . P A 2
C8A C 0.5270(7) 0.2840(8) -0.2007(18) 0.082(2) Uani 0.338(5) 1 d G . P A 2
H8A H 0.5388 0.2106 -0.2104 0.099 Uiso 0.338(5) 1 calc R . P 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 105.5(2) . . ?
O1 C1 C2 127.8(3) . . ?
O1 C1 N1 126.7(3) . . ?
C3 C2 C1 101.6(2) . . ?
C3 C2 C13 112.6(2) . . ?
C13 C2 C1 109.0(2) . . ?
N3 C2 C1 110.9(2) . . ?
N3 C2 C3 114.8(2) . . ?
N3 C2 C13 107.9(2) . . ?
C4 C3 C2 110.7(2) . . ?
C4 C3 C16 130.2(3) . . ?
C16 C3 C2 119.1(2) . . ?
C3 C4 C5 132.5(3) . . ?
C3 C4 N1 109.0(3) . . ?
N1 C4 C5 118.5(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N3 C6 C7 118.6(3) . . ?
N3 C6 C7A 113.5(6) . . ?
O2 C6 C7 119.9(3) . . ?
O2 C6 N3 121.3(3) . . ?
O2 C6 C7A 125.0(6) . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C7 120.0 . . ?
C7 C12 H12 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 C12 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C10 H10 120.0 . . ?
C11 C10 C9 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C9 H9 120.0 . . ?
C8 C9 C10 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C8 H8 120.0 . . ?
C9 C8 C7 120.0 . . ?
C7 C8 H8 120.0 . . ?
C12 C7 C6 116.5(3) . . ?
C8 C7 C6 123.5(3) . . ?
C8 C7 C12 120.0 . . ?
O3 C13 C2 123.0(3) . . ?
O3 C13 O4 126.7(3) . . ?
O4 C13 C2 110.2(3) . . ?
H14A C14 H14B 108.4 . . ?
C15 C14 H14A 110.1 . . ?
C15 C14 H14B 110.1 . . ?
O4 C14 H14A 110.1 . . ?
O4 C14 H14B 110.1 . . ?
O4 C14 C15 108.1(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O5 C16 C3 122.2(3) . . ?
O5 C16 O6 124.1(3) . . ?
O6 C16 C3 113.7(2) . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O6 C17 H17A 109.5 . . ?
O6 C17 H17B 109.5 . . ?
O6 C17 H17C 109.5 . . ?
O7 C18 N2 125.8(3) . . ?
O7 C18 O8 126.0(3) . . ?
O8 C18 N2 108.1(3) . . ?
H19A C19 H19B 108.5 . . ?
C20 C19 H19A 110.2 . . ?
C20 C19 H19B 110.2 . . ?
O8 C19 H19A 110.2 . . ?
O8 C19 H19B 110.2 . . ?
O8 C19 C20 107.6(4) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 N1 C4 113.0(2) . . ?
N2 N1 C1 122.2(3) . . ?
N2 N1 C4 123.0(3) . . ?
C18 N2 N1 118.5(3) . . ?
C18 N2 H2 118(3) . . ?
N1 N2 H2 118(3) . . ?
C2 N3 H3 118(2) . . ?
C6 N3 C2 120.7(2) . . ?
C6 N3 H3 120(2) . . ?
C13 O4 C14 116.4(3) . . ?
C16 O6 C17 115.5(3) . . ?
C18 O8 C19 116.0(3) . . ?
C12A C7A C6 117.4(8) . . ?
C12A C7A C8A 120.0 . . ?
C8A C7A C6 122.6(8) . . ?
C7A C12A H12A 120.0 . . ?
C11A C12A C7A 120.0 . . ?
C11A C12A H12A 120.0 . . ?
C12A C11A H11A 120.0 . . ?
C12A C11A C10A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
C11A C10A H10A 120.0 . . ?
C9A C10A C11A 120.0 . . ?
C9A C10A H10A 120.0 . . ?
C10A C9A H9A 120.0 . . ?
C10A C9A C8A 120.0 . . ?
C8A C9A H9A 120.0 . . ?
C7A C8A H8A 120.0 . . ?
C9A C8A C7A 120.0 . . ?
C9A C8A H8A 120.0 . . ?
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 C2 1.554(4) . ?
C1 N1 1.381(4) . ?
C1 O1 1.192(4) . ?
C2 C3 1.513(4) . ?
C2 C13 1.532(4) . ?
C2 N3 1.447(4) . ?
C3 C4 1.345(4) . ?
C3 C16 1.463(4) . ?
C4 C5 1.482(4) . ?
C4 N1 1.396(4) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.527(4) . ?
C6 N3 1.344(4) . ?
C6 O2 1.222(4) . ?
C6 C7A 1.449(9) . ?
C12 H12 0.9300 . ?
C12 C11 1.3900 . ?
C12 C7 1.3900 . ?
C11 H11 0.9300 . ?
C11 C10 1.3900 . ?
C10 H10 0.9300 . ?
C10 C9 1.3900 . ?
C9 H9 0.9300 . ?
C9 C8 1.3900 . ?
C8 H8 0.9300 . ?
C8 C7 1.3900 . ?
C13 O3 1.195(4) . ?
C13 O4 1.312(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.485(6) . ?
C14 O4 1.450(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 O5 1.203(4) . ?
C16 O6 1.331(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C17 O6 1.455(4) . ?
C18 N2 1.360(4) . ?
C18 O7 1.194(4) . ?
C18 O8 1.337(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.488(7) . ?
C19 O8 1.446(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N1 N2 1.381(3) . ?
N2 H2 0.87(6) . ?
N3 H3 0.85(2) . ?
C7A C12A 1.3900 . ?
C7A C8A 1.3900 . ?
C12A H12A 0.9300 . ?
C12A C11A 1.3900 . ?
C11A H11A 0.9300 . ?
C11A C10A 1.3900 . ?
C10A H10A 0.9300 . ?
C10A C9A 1.3900 . ?
C9A H9A 0.9300 . ?
C9A C8A 1.3900 . ?
C8A H8A 0.9300 . ?
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
N2 H2 O5 0.87(6) 2.04(6) 2.859(4) 156(4) 4_655
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 C2 C3 C4 1.7(3) . . . . ?
C1 C2 C3 C16 -179.3(2) . . . . ?
C1 C2 C13 O3 126.3(3) . . . . ?
C1 C2 C13 O4 -53.3(3) . . . . ?
C1 C2 N3 C6 46.9(4) . . . . ?
C1 N1 N2 C18 82.7(4) . . . . ?
C2 C1 N1 C4 4.5(3) . . . . ?
C2 C1 N1 N2 169.7(3) . . . . ?
C2 C3 C4 C5 -179.1(3) . . . . ?
C2 C3 C4 N1 0.9(3) . . . . ?
C2 C3 C16 O5 -6.9(4) . . . . ?
C2 C3 C16 O6 170.9(3) . . . . ?
C2 C13 O4 C14 -178.7(3) . . . . ?
C3 C2 C13 O3 -121.8(3) . . . . ?
C3 C2 C13 O4 58.5(3) . . . . ?
C3 C2 N3 C6 -67.4(3) . . . . ?
C3 C4 N1 C1 -3.6(3) . . . . ?
C3 C4 N1 N2 -168.6(3) . . . . ?
C3 C16 O6 C17 179.7(3) . . . . ?
C4 C3 C16 O5 171.9(3) . . . . ?
C4 C3 C16 O6 -10.3(4) . . . . ?
C4 N1 N2 C18 -113.5(3) . . . . ?
C5 C4 N1 C1 176.4(3) . . . . ?
C5 C4 N1 N2 11.3(4) . . . . ?
C6 C7A C12A C11A 179.1(12) . . . . ?
C6 C7A C8A C9A -179.0(13) . . . . ?
C12 C11 C10 C9 0.0 . . . . ?
C11 C12 C7 C6 178.2(5) . . . . ?
C11 C12 C7 C8 0.0 . . . . ?
C11 C10 C9 C8 0.0 . . . . ?
C10 C9 C8 C7 0.0 . . . . ?
C9 C8 C7 C6 -178.1(5) . . . . ?
C9 C8 C7 C12 0.0 . . . . ?
C7 C6 N3 C2 171.1(3) . . . . ?
C7 C12 C11 C10 0.0 . . . . ?
C13 C2 C3 C4 -114.7(3) . . . . ?
C13 C2 C3 C16 64.3(3) . . . . ?
C13 C2 N3 C6 166.2(3) . . . . ?
C15 C14 O4 C13 170.6(3) . . . . ?
C16 C3 C4 C5 2.0(5) . . . . ?
C16 C3 C4 N1 -178.0(3) . . . . ?
C20 C19 O8 C18 172.1(4) . . . . ?
N1 C1 C2 C3 -3.6(3) . . . . ?
N1 C1 C2 C13 115.4(3) . . . . ?
N1 C1 C2 N3 -126.0(3) . . . . ?
N2 C18 O8 C19 -175.9(3) . . . . ?
N3 C2 C3 C4 121.4(3) . . . . ?
N3 C2 C3 C16 -59.6(4) . . . . ?
N3 C2 C13 O3 5.8(4) . . . . ?
N3 C2 C13 O4 -173.8(2) . . . . ?
N3 C6 C7 C12 -163.1(3) . . . . ?
N3 C6 C7 C8 15.0(6) . . . . ?
N3 C6 C7A C12A 153.4(7) . . . . ?
N3 C6 C7A C8A -27.6(10) . . . . ?
O1 C1 C2 C3 178.9(3) . . . . ?
O1 C1 C2 C13 -62.1(4) . . . . ?
O1 C1 C2 N3 56.5(4) . . . . ?
O1 C1 N1 C4 -177.9(3) . . . . ?
O1 C1 N1 N2 -12.7(5) . . . . ?
O2 C6 C7 C12 13.6(5) . . . . ?
O2 C6 C7 C8 -168.3(4) . . . . ?
O2 C6 N3 C2 -5.5(4) . . . . ?
O2 C6 C7A C12A -21.4(12) . . . . ?
O2 C6 C7A C8A 157.6(6) . . . . ?
O3 C13 O4 C14 1.6(5) . . . . ?
O5 C16 O6 C17 -2.5(4) . . . . ?
O7 C18 N2 N1 13.1(5) . . . . ?
O7 C18 O8 C19 0.7(5) . . . . ?
O8 C18 N2 N1 -170.3(3) . . . . ?
C7A C6 N3 C2 179.5(7) . . . . ?
C7A C12A C11A C10A 0.0 . . . . ?
C12A C7A C8A C9A 0.0 . . . . ?
C12A C11A C10A C9A 0.0 . . . . ?
C11A C10A C9A C8A 0.0 . . . . ?
C10A C9A C8A C7A 0.0 . . . . ?
C8A C7A C12A C11A 0.0 . . . . ?
