#------------------------------------------------------------------------------
#$Date: 2024-12-06 22:22:56 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296645 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/35/7063527.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_7063527
loop_
_publ_author_name
'Golubev, Artem A.'
'Simdianov, Ivan V.'
'Smetanin, Ilia A.'
'Agafonova, Anastasiya V.'
'Rostovskii, Nikolai V.'
'Khlebnikov, Alexander F.'
'Novikov, Mikhail S.'
_publ_section_title
;
 2-Azidoazirines suitable for click chemistry: synthesis of
 1-(2H-azirin-2-yl)-1H-1,2,3-triazoles
;
_journal_issue                   47
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              19957
_journal_page_last               19962
_journal_paper_doi               10.1039/D4NJ03517H
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C18 H14 N4 O2, C18 H15 N4 O2'
_chemical_formula_sum            'C36 H29 N8 O4'
_chemical_formula_weight         637.67
_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     dual
_audit_creation_date             2024-04-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-04-06 deposited with the CCDC.	2024-11-10 downloaded from the CCDC.
;
_cell_angle_alpha                97.1059(8)
_cell_angle_beta                 91.7213(10)
_cell_angle_gamma                94.7055(10)
_cell_formula_units_Z            2
_cell_length_a                   7.88082(11)
_cell_length_b                   12.52489(13)
_cell_length_c                   16.01630(14)
_cell_measurement_reflns_used    20384
_cell_measurement_temperature    100.01(13)
_cell_measurement_theta_max      77.1760
_cell_measurement_theta_min      2.7580
_cell_volume                     1562.19(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  28.00   0.50    0.50    --  -47.20  19.00  60.00  106
  2  ω    -26.00  26.00   0.50    0.50    --   47.20 -19.00-120.00  104
  3  ω    -27.00  25.00   0.50    0.50    --   47.20 -19.00-180.00  104
  4  ω     33.00  70.00   0.50    0.50    --   47.20  57.00 -60.00   74
  5  ω     74.00 115.00   0.50    0.50    --   47.20  57.00 -60.00   82
  6  ω     80.00 108.00   0.50    0.50    --   47.20 125.00  60.00   56
  7  ω     90.00 139.00   0.50    2.10    --  107.75 117.00  94.00   98
  8  ω    142.00 171.00   0.50    2.10    --  107.75 125.00  60.00   58
  9  ω    106.00 178.00   0.50    2.10    --  107.75  15.00 -30.00  144
 10  ω    126.00 176.00   0.50    2.10    --  107.75  45.00-120.00  100
 11  ω     95.00 178.00   0.50    2.10    --  107.75  45.00-180.00  166
 12  ω     90.00 116.00   0.50    0.50    --   47.20 162.00-114.00   52
 13  ω     53.00  87.00   0.50    0.50    --   47.20 162.00-114.00   68
 14  ω     91.00 117.00   0.50    2.10    --  107.75 162.00-114.00   52
 15  ω    126.00 155.00   0.50    2.10    --  107.75 162.00-114.00   58
 16  ω     85.00 111.00   0.50    2.10    --  107.75 125.00  60.00   52
 17  ω     39.00  71.00   0.50    2.10    --  107.75 -61.00-120.00   64
 18  ω     59.00  99.00   0.50    2.10    --  107.75 -94.00-150.00   80
 19  ω     62.00  88.00   0.50    2.10    --  107.75 -94.00-180.00   52
 20  ω     62.00  87.00   0.50    2.10    --  107.75-162.00-142.00   50
 21  ω     76.00 112.00   0.50    2.10    --  107.75-125.00 -60.00   72
 22  ω     82.00 109.00   0.50    2.10    --  107.75-117.00   7.00   54
 23  ω     78.00 104.00   0.50    2.10    --  107.75 -94.00  30.00   52
 24  ω     63.00 111.00   0.50    2.10    --  107.75-125.00 120.00   96
 25  ω     45.00  71.00   0.50    2.10    --  107.75 -61.00  30.00   52
 26  ω     35.00  71.00   0.50    2.10    --  107.75 -61.00  60.00   72
 27  ω     36.00 104.00   0.50    2.10    --  107.75 -94.00   0.00  136
 28  ω     35.00 112.00   0.50    2.10    --  107.75-125.00 -90.00  154
 29  ω     83.00 108.00   0.50    0.50    --   47.20-162.00-142.00   50
 30  ω     43.00 112.00   0.50    2.10    --  107.75-125.00-150.00  138
 31  ω     35.00 110.00   0.50    2.10    --  107.75-125.00-180.00  150
 32  ω     38.00  68.00   0.50    2.10    --  107.75 -61.00 -90.00   60
 33  ω     37.00  70.00   0.50    2.10    --  107.75 -61.00-180.00   66
 34  ω     22.00  48.00   0.50    0.50    --   47.20-117.00   7.00   52
 35  ω     36.00  70.00   0.50    2.10    --  107.75 -94.00  30.00   68
 36  ω    -90.00 -11.00   0.50    0.50    --  -47.20 117.00  94.00  158
 37  ω    -68.00 -38.00   0.50    2.10    -- -106.00  61.00  60.00   60
 38  ω    -72.00 -34.00   0.50    2.10    -- -106.00 125.00   0.00   76
 39  ω    -58.00 -33.00   0.50    2.10    -- -106.00 108.00 -81.47   50
 40  ω    -65.00 -39.00   0.50    2.10    -- -106.00  61.00 -90.00   52
 41  ω    -62.00 -33.00   0.50    2.10    -- -106.00  61.00 -60.00   58
 42  ω    -99.00 -74.00   0.50    0.50    --  -47.20 162.00-114.00   50
 43  ω   -100.00 -75.00   0.50    0.50    --  -47.20-125.00  60.00   50
 44  ω   -139.00-113.00   0.50    2.10    -- -106.00-117.00   7.00   52
 45  ω   -140.00 -99.00   0.50    2.10    -- -106.00 -61.00 -60.00   82
 46  ω   -135.00 -86.00   0.50    2.10    -- -106.00 -94.00-120.00   98
 47  ω   -127.00-102.00   0.50    2.10    -- -106.00-162.00-142.00   50
 48  ω    -96.00 -50.00   0.50    0.50    --  -47.20-162.00-142.00   92
 49  ω   -125.00 -92.00   0.50    2.10    -- -106.00 -15.00  60.00   66
 50  ω    -98.00 -34.00   0.50    2.10    -- -106.00  77.00 120.00  128
 51  ω   -108.00 -68.00   0.50    2.10    -- -106.00 117.00  94.00   80
 52  ω   -112.00 -56.00   0.50    2.10    -- -106.00 125.00 150.00  112
 53  ω   -109.00 -83.00   0.50    2.10    -- -106.00 115.00  63.26   52
 54  ω   -120.00 -94.00   0.50    2.10    -- -106.00 137.00 -38.04   52
 55  ω   -107.00 -70.00   0.50    2.10    -- -106.00 108.00 -81.47   74
 56  ω   -136.00 -98.00   0.50    2.10    -- -106.00 162.00-114.00   76
 57  ω   -149.00 -92.00   0.50    2.10    -- -106.00 -15.00 -30.00  114
 58  ω   -172.00-147.00   0.50    2.10    -- -106.00 -61.00 -60.00   50
 59  ω   -176.00-151.00   0.50    2.10    -- -106.00 -94.00-120.00   50
 60  ω   -176.00-121.00   0.50    2.10    -- -106.00 -45.00 -90.00  110
 61  ω     82.00 117.00   0.50    0.50    --   47.20 125.00 150.00   70
 62  ω    -56.00 -31.00   0.50    0.50    --   10.00 156.00 170.94   50
 63  ω    -20.00   9.00   0.50    0.50    --   14.00 101.00  22.26   58
 64  ω     -8.00  17.00   0.50    0.50    --   26.00 100.00 150.86   50
 65  ω     -3.00  22.00   0.50    0.50    --   30.00  98.00-117.21   50
 66  ω     12.00  37.00   0.50    0.50    --   38.00  85.00 -29.26   50
 67  ω     15.00  40.00   0.50    0.50    --   42.00  87.00 137.21   50
 68  ω     17.00  42.00   0.50    0.50    --   46.00  90.00-137.66   50
 69  ω    -67.00 -40.00   0.50    0.50    --  -47.20 -19.00-150.00   54
 70  ω     25.00  54.00   0.50    0.50    --   47.20  77.00   0.00   58
 71  ω     30.00  56.00   0.50    0.50    --   54.00  79.00 164.31   52
 72  ω     33.00  59.00   0.50    0.50    --   54.00  78.00 -65.50   52
 73  ω     30.00  83.00   0.50    0.50    --   54.00  79.00   3.32  106
 74  ω     35.00  61.00   0.50    0.50    --   54.00  79.00  19.25   52
 75  ω     35.00  69.00   0.50    0.50    --   58.00  78.00  63.28   68
 76  ω     35.00  60.00   0.50    0.50    --   58.00  77.00 119.16   50
 77  ω     35.00  61.00   0.50    0.50    --   58.00  77.00-167.89   52
 78  ω     38.00  63.00   0.50    0.50    --   62.00  80.00-108.83   50
 79  ω     41.00  67.00   0.50    0.50    --   62.00  75.00-146.05   52
 80  ω    -72.00 -43.00   0.50    0.50    --  -66.00 -78.00 -48.27   58
 81  ω     44.00  70.00   0.50    0.50    --   66.00  76.00  22.00   52
 82  ω     44.00  81.00   0.50    0.50    --   66.00  76.00 141.21   74
 83  ω     42.00  68.00   0.50    0.50    --   66.00  79.00 -68.39   52
 84  ω    -77.00 -51.00   0.50    0.50    --  -70.00 -68.00  82.37   52
 85  ω     48.00  73.00   0.50    0.50    --   70.00  76.00  81.39   50
 86  ω     47.00  73.00   0.50    0.50    --   70.00  77.00  40.54   52
 87  ω    -79.00 -53.00   0.50    0.50    --  -74.00 -75.00-173.38   52
 88  ω    -76.00 -51.00   0.50    0.50    --  -74.00 -76.00-114.15   50
 89  ω     52.00  78.00   0.50    0.50    --   74.00  76.00 167.33   52
 90  ω    -93.00 -58.00   0.50    2.10    --  -78.00 -70.00-127.69   70
 91  ω    -85.00 -59.00   0.50    2.10    --  -78.00 -73.00 -73.95   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0932076000
_diffrn_orient_matrix_UB_12      -0.0931255000
_diffrn_orient_matrix_UB_13      -0.0603959000
_diffrn_orient_matrix_UB_21      0.0929561000
_diffrn_orient_matrix_UB_22      0.0412669000
_diffrn_orient_matrix_UB_23      -0.0745677000
_diffrn_orient_matrix_UB_31      0.1456277000
_diffrn_orient_matrix_UB_32      -0.0714460000
_diffrn_orient_matrix_UB_33      0.0142558000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            34701
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.438
_diffrn_reflns_theta_min         2.783
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.750
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       prism
_exptl_crystal_F_000             666
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0017(2)
_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   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         6491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0485P)²+0.4770P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.0987
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5757
_reflns_number_total             6491
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj03517h2.cif
_cod_data_source_block           15347_agf16
_cod_depositor_comments
'Adding full bibliography for 7063527--7063529.cif.'
_cod_database_code               7063527
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C18 H14 O2 N4'
_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   0.956
_shelx_estimated_absorpt_t_min   0.929
_diffrn_oxdiff_digest_frames
;
0182137e6bc5cecce76d73b736b07ba89d00031650b
;
_diffrn_oxdiff_digest_hkl
;
01975d05f5cb222f5ac498d91845406c1b1784
;
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 N37(H37), C35(H35), C14(H14), C30(H30), C26(H26), C6(H6), C20(H20), C44(H44),
 C16(H16), C29(H29), C27(H27), C28(H28), C19(H19), C43(H43), C40(H40), C2(H2),
 C5(H5), C18(H18), C17(H17), C3(H3), C42(H42), C4(H4), C41(H41)
1.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C47(H47A,H47B,H47C)
;
_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 1.330
_oxdiff_exptl_absorpt_empirical_full_min 0.727
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
O22 O 0.63601(11) 0.92942(7) 0.17086(6) 0.02578(19) Uani 1 1 d . . . . .
O48 O 0.81614(12) 0.65630(7) 0.18013(6) 0.0296(2) Uani 1 1 d . . . . .
O24 O 0.67521(11) 0.88362(8) 0.30150(6) 0.0304(2) Uani 1 1 d . . . . .
O46 O 0.83607(11) 0.62584(8) 0.31567(6) 0.0290(2) Uani 1 1 d . . . . .
N13 N 0.29679(12) 0.88894(8) 0.17169(6) 0.0208(2) Uani 1 1 d . . . . .
N34 N 0.49655(12) 0.57416(8) 0.32011(6) 0.0206(2) Uani 1 1 d . . . . .
N11 N 0.16437(13) 0.93527(8) 0.06530(7) 0.0249(2) Uani 1 1 d . . . . .
N33 N 0.46119(13) 0.59477(8) 0.16665(6) 0.0240(2) Uani 1 1 d . . . . .
N7 N 0.31606(13) 0.85174(8) 0.32209(7) 0.0246(2) Uani 1 1 d . . . . .
N38 N 0.39858(14) 0.48546(8) 0.33574(7) 0.0264(2) Uani 1 1 d . . . . .
N37 N 0.32920(14) 0.51091(8) 0.40758(7) 0.0270(2) Uani 1 1 d . . . . .
H37 H 0.261467 0.468187 0.431860 0.032 Uiso 1 1 calc R . . . .
N12 N 0.24396(13) 0.97461(8) 0.13702(7) 0.0253(2) Uani 1 1 d . . . . .
C35 C 0.48784(15) 0.65644(9) 0.38235(7) 0.0210(2) Uani 1 1 d . . . . .
H35 H 0.542770 0.725595 0.386243 0.025 Uiso 1 1 calc R . . . .
C32 C 0.50455(14) 0.50021(10) 0.16889(7) 0.0212(2) Uani 1 1 d . . . . .
C10 C 0.16498(14) 0.82521(9) 0.05403(7) 0.0203(2) Uani 1 1 d . . . . .
C15 C 0.08538(14) 0.75719(10) -0.02013(7) 0.0211(2) Uani 1 1 d . . . . .
C21 C 0.58465(15) 0.90342(9) 0.24430(8) 0.0220(2) Uani 1 1 d . . . . .
C25 C 0.48940(14) 0.39220(9) 0.12454(7) 0.0209(2) Uani 1 1 d . . . . .
C8 C 0.39460(15) 0.90432(9) 0.24977(7) 0.0213(2) Uani 1 1 d . . . . .
C14 C 0.25079(15) 0.79560(9) 0.12204(7) 0.0219(2) Uani 1 1 d . . . . .
H14 H 0.272498 0.726229 0.131774 0.026 Uiso 1 1 calc R . . . .
C36 C 0.38022(15) 0.61566(9) 0.43856(7) 0.0217(2) Uani 1 1 d . . . . .
C1 C 0.27616(15) 1.05124(10) 0.37338(8) 0.0225(2) Uani 1 1 d . . . . .
C30 C 0.41425(15) 0.37362(10) 0.04323(7) 0.0230(2) Uani 1 1 d . . . . .
H30 H 0.375283 0.430460 0.017935 0.028 Uiso 1 1 calc R . . . .
C9 C 0.32018(15) 0.95304(10) 0.32538(7) 0.0222(2) Uani 1 1 d . . . . .
C26 C 0.54762(15) 0.30742(10) 0.16312(8) 0.0239(2) Uani 1 1 d . . . . .
H26 H 0.598038 0.320319 0.217066 0.029 Uiso 1 1 calc R . . . .
C6 C 0.29845(15) 1.14797(10) 0.33847(8) 0.0245(2) Uani 1 1 d . . . . .
H6 H 0.341092 1.148725 0.285009 0.029 Uiso 1 1 calc R . . . .
C20 C -0.00579(15) 0.80247(10) -0.08112(8) 0.0247(3) Uani 1 1 d . . . . .
H20 H -0.017701 0.876267 -0.074507 0.030 Uiso 1 1 calc R . . . .
C39 C 0.31474(15) 0.66856(10) 0.51644(7) 0.0226(2) Uani 1 1 d . . . . .
C44 C 0.33243(16) 0.78077(10) 0.53510(8) 0.0252(3) Uani 1 1 d . . . . .
H44 H 0.388262 0.822379 0.498375 0.030 Uiso 1 1 calc R . . . .
C16 C 0.09996(15) 0.64605(10) -0.03095(8) 0.0243(2) Uani 1 1 d . . . . .
H16 H 0.159974 0.615089 0.009375 0.029 Uiso 1 1 calc R . . . .
C31 C 0.57533(15) 0.57435(9) 0.24080(7) 0.0203(2) Uani 1 1 d . . . . .
C29 C 0.39843(16) 0.27005(10) 0.00081(8) 0.0266(3) Uani 1 1 d . . . . .
H29 H 0.349958 0.257080 -0.053540 0.032 Uiso 1 1 calc R . . . .
C45 C 0.75536(15) 0.62400(9) 0.24134(8) 0.0224(2) Uani 1 1 d . . . . .
C27 C 0.52959(16) 0.20388(10) 0.12030(8) 0.0268(3) Uani 1 1 d . . . . .
H27 H 0.567380 0.146755 0.145632 0.032 Uiso 1 1 calc R . . . .
C28 C 0.45505(17) 0.18519(10) 0.03946(8) 0.0278(3) Uani 1 1 d . . . . .
H28 H 0.442957 0.115455 0.011005 0.033 Uiso 1 1 calc R . . . .
C19 C -0.07852(16) 0.73719(12) -0.15156(8) 0.0292(3) Uani 1 1 d . . . . .
H19 H -0.138152 0.767788 -0.192225 0.035 Uiso 1 1 calc R . . . .
C43 C 0.26735(16) 0.83093(11) 0.60807(8) 0.0285(3) Uani 1 1 d . . . . .
H43 H 0.279792 0.905802 0.620004 0.034 Uiso 1 1 calc R . . . .
C40 C 0.23057(17) 0.60768(11) 0.57216(8) 0.0293(3) Uani 1 1 d . . . . .
H40 H 0.217907 0.532776 0.560596 0.035 Uiso 1 1 calc R . . . .
C2 C 0.21315(17) 1.04949(11) 0.45393(8) 0.0282(3) Uani 1 1 d . . . . .
H2 H 0.198088 0.984841 0.476856 0.034 Uiso 1 1 calc R . . . .
C5 C 0.25657(17) 1.24265(10) 0.38406(9) 0.0294(3) Uani 1 1 d . . . . .
H5 H 0.269795 1.307328 0.361064 0.035 Uiso 1 1 calc R . . . .
C18 C -0.06336(16) 0.62712(12) -0.16200(8) 0.0302(3) Uani 1 1 d . . . . .
H18 H -0.112601 0.584029 -0.209404 0.036 Uiso 1 1 calc R . . . .
C17 C 0.02569(16) 0.58127(11) -0.10138(8) 0.0288(3) Uani 1 1 d . . . . .
H17 H 0.035602 0.507252 -0.107925 0.035 Uiso 1 1 calc R . . . .
C3 C 0.17347(18) 1.14502(12) 0.49913(8) 0.0319(3) Uani 1 1 d . . . . .
H3 H 0.132483 1.145021 0.552981 0.038 Uiso 1 1 calc R . . . .
C42 C 0.18403(17) 0.76952(12) 0.66299(8) 0.0311(3) Uani 1 1 d . . . . .
H42 H 0.140631 0.802952 0.711924 0.037 Uiso 1 1 calc R . . . .
C4 C 0.19500(17) 1.24102(11) 0.46389(9) 0.0314(3) Uani 1 1 d . . . . .
H4 H 0.167643 1.304984 0.494404 0.038 Uiso 1 1 calc R . . . .
C23 C 0.81878(16) 0.93481(11) 0.15946(9) 0.0311(3) Uani 1 1 d . . . . .
H23A H 0.842026 0.952452 0.104050 0.047 Uiso 1 1 calc GR . . . .
H23B H 0.859852 0.866161 0.166096 0.047 Uiso 1 1 calc GR . . . .
H23C H 0.875108 0.989382 0.200713 0.047 Uiso 1 1 calc GR . . . .
C41 C 0.16557(18) 0.65811(12) 0.64476(9) 0.0336(3) Uani 1 1 d . . . . .
H41 H 0.109127 0.616819 0.681499 0.040 Uiso 1 1 calc R . . . .
C47 C 1.00984(18) 0.67538(14) 0.32025(10) 0.0414(4) Uani 1 1 d . . . . .
H47A H 1.076168 0.635074 0.280264 0.062 Uiso 1 1 calc GR . . . .
H47B H 1.058391 0.675501 0.375958 0.062 Uiso 1 1 calc GR . . . .
H47C H 1.009823 0.748302 0.307550 0.062 Uiso 1 1 calc GR . . . .
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
C21 O22 C23 116.15(10) . . ?
C45 O46 C47 114.34(11) . . ?
N12 N13 C8 120.76(10) . . ?
C14 N13 N12 111.20(10) . . ?
C14 N13 C8 127.99(10) . . ?
N38 N34 C31 119.44(10) . . ?
C35 N34 N38 111.00(10) . . ?
C35 N34 C31 129.12(10) . . ?
N12 N11 C10 109.61(10) . . ?
C32 N33 C31 61.90(8) . . ?
C9 N7 C8 61.87(8) . . ?
N37 N38 N34 106.64(10) . . ?
N38 N37 H37 125.1 . . ?
N38 N37 C36 109.85(10) . . ?
C36 N37 H37 125.1 . . ?
N11 N12 N13 106.40(9) . . ?
N34 C35 H35 127.6 . . ?
N34 C35 C36 104.82(10) . . ?
C36 C35 H35 127.6 . . ?
N33 C32 C25 143.85(11) . . ?
N33 C32 C31 68.01(8) . . ?
C25 C32 C31 148.12(11) . . ?
N11 C10 C15 122.94(10) . . ?
N11 C10 C14 107.87(10) . . ?
C14 C10 C15 129.19(11) . . ?
C20 C15 C10 120.62(11) . . ?
C16 C15 C10 120.36(10) . . ?
C16 C15 C20 119.02(11) . . ?
O22 C21 C8 111.24(10) . . ?
O24 C21 O22 125.98(11) . . ?
O24 C21 C8 122.76(11) . . ?
C30 C25 C32 119.29(11) . . ?
C26 C25 C32 119.99(11) . . ?
C26 C25 C30 120.72(11) . . ?
N13 C8 N7 116.27(10) . . ?
N13 C8 C21 116.74(10) . . ?
N13 C8 C9 119.45(10) . . ?
C21 C8 N7 115.86(9) . . ?
C9 C8 N7 50.10(7) . . ?
C9 C8 C21 120.75(10) . . ?
N13 C14 C10 104.92(10) . . ?
N13 C14 H14 127.5 . . ?
C10 C14 H14 127.5 . . ?
N37 C36 C35 107.69(10) . . ?
N37 C36 C39 122.03(11) . . ?
C35 C36 C39 130.18(11) . . ?
C6 C1 C9 119.02(11) . . ?
C6 C1 C2 120.66(11) . . ?
C2 C1 C9 120.33(11) . . ?
C25 C30 H30 120.3 . . ?
C29 C30 C25 119.41(11) . . ?
C29 C30 H30 120.3 . . ?
N7 C9 C8 68.02(9) . . ?
N7 C9 C1 145.29(12) . . ?
C1 C9 C8 146.68(11) . . ?
C25 C26 H26 120.3 . . ?
C27 C26 C25 119.33(11) . . ?
C27 C26 H26 120.3 . . ?
C1 C6 H6 120.3 . . ?
C5 C6 C1 119.44(12) . . ?
C5 C6 H6 120.3 . . ?
C15 C20 H20 120.0 . . ?
C19 C20 C15 119.92(12) . . ?
C19 C20 H20 120.0 . . ?
C44 C39 C36 120.62(11) . . ?
C40 C39 C36 120.52(11) . . ?
C40 C39 C44 118.85(11) . . ?
C39 C44 H44 119.7 . . ?
C43 C44 C39 120.58(12) . . ?
C43 C44 H44 119.7 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.62(11) . . ?
C17 C16 H16 119.7 . . ?
N34 C31 N33 116.24(9) . . ?
N34 C31 C32 119.27(10) . . ?
N34 C31 C45 117.48(10) . . ?
C32 C31 N33 50.09(7) . . ?
C32 C31 C45 120.39(10) . . ?
C45 C31 N33 115.01(9) . . ?
C30 C29 H29 120.0 . . ?
C30 C29 C28 119.97(12) . . ?
C28 C29 H29 120.0 . . ?
O48 C45 O46 125.54(11) . . ?
O48 C45 C31 122.39(11) . . ?
O46 C45 C31 112.06(10) . . ?
C26 C27 H27 120.0 . . ?
C26 C27 C28 120.08(11) . . ?
C28 C27 H27 120.0 . . ?
C29 C28 H28 119.8 . . ?
C27 C28 C29 120.49(12) . . ?
C27 C28 H28 119.8 . . ?
C20 C19 H19 119.6 . . ?
C18 C19 C20 120.78(12) . . ?
C18 C19 H19 119.6 . . ?
C44 C43 H43 120.0 . . ?
C42 C43 C44 120.03(13) . . ?
C42 C43 H43 120.0 . . ?
C39 C40 H40 119.8 . . ?
C41 C40 C39 120.35(13) . . ?
C41 C40 H40 119.8 . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.24(12) . . ?
C3 C2 H2 120.4 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 C6 119.91(12) . . ?
C4 C5 H5 120.0 . . ?
C19 C18 H18 120.1 . . ?
C19 C18 C17 119.70(12) . . ?
C17 C18 H18 120.1 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 119.95(12) . . ?
C18 C17 H17 120.0 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.87(13) . . ?
C4 C3 H3 120.1 . . ?
C43 C42 H42 120.1 . . ?
C43 C42 C41 119.71(12) . . ?
C41 C42 H42 120.1 . . ?
C5 C4 C3 120.87(12) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
O22 C23 H23A 109.5 . . ?
O22 C23 H23B 109.5 . . ?
O22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C40 C41 H41 119.8 . . ?
C42 C41 C40 120.49(13) . . ?
C42 C41 H41 119.8 . . ?
O46 C47 H47A 109.5 . . ?
O46 C47 H47B 109.5 . . ?
O46 C47 H47C 109.5 . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 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
O22 C21 1.3249(15) . ?
O22 C23 1.4545(15) . ?
O48 C45 1.2037(15) . ?
O24 C21 1.2067(15) . ?
O46 C45 1.3295(15) . ?
O46 C47 1.4522(16) . ?
N13 N12 1.3564(14) . ?
N13 C8 1.4329(15) . ?
N13 C14 1.3466(15) . ?
N34 N38 1.3538(14) . ?
N34 C35 1.3498(15) . ?
N34 C31 1.4307(15) . ?
N11 N12 1.3120(15) . ?
N11 C10 1.3684(15) . ?
N33 C32 1.2637(16) . ?
N33 C31 1.5276(15) . ?
N7 C8 1.5243(15) . ?
N7 C9 1.2611(16) . ?
N38 N37 1.3040(15) . ?
N37 H37 0.8600 . ?
N37 C36 1.3673(16) . ?
C35 H35 0.9300 . ?
C35 C36 1.3708(16) . ?
C32 C25 1.4421(16) . ?
C32 C31 1.4532(16) . ?
C10 C15 1.4654(17) . ?
C10 C14 1.3704(16) . ?
C15 C20 1.3978(16) . ?
C15 C16 1.3960(17) . ?
C21 C8 1.5038(16) . ?
C25 C30 1.3989(16) . ?
C25 C26 1.3947(17) . ?
C8 C9 1.4496(17) . ?
C14 H14 0.9300 . ?
C36 C39 1.4669(17) . ?
C1 C9 1.4409(17) . ?
C1 C6 1.3964(17) . ?
C1 C2 1.3982(17) . ?
C30 H30 0.9300 . ?
C30 C29 1.3821(17) . ?
C26 H26 0.9300 . ?
C26 C27 1.3842(18) . ?
C6 H6 0.9300 . ?
C6 C5 1.3830(18) . ?
C20 H20 0.9300 . ?
C20 C19 1.3877(18) . ?
C39 C44 1.3947(17) . ?
C39 C40 1.3924(17) . ?
C44 H44 0.9300 . ?
C44 C43 1.3895(18) . ?
C16 H16 0.9300 . ?
C16 C17 1.3889(18) . ?
C31 C45 1.5009(16) . ?
C29 H29 0.9300 . ?
C29 C28 1.3913(18) . ?
C27 H27 0.9300 . ?
C27 C28 1.3903(19) . ?
C28 H28 0.9300 . ?
C19 H19 0.9300 . ?
C19 C18 1.383(2) . ?
C43 H43 0.9300 . ?
C43 C42 1.384(2) . ?
C40 H40 0.9300 . ?
C40 C41 1.3859(19) . ?
C2 H2 0.9300 . ?
C2 C3 1.3836(19) . ?
C5 H5 0.9300 . ?
C5 C4 1.383(2) . ?
C18 H18 0.9300 . ?
C18 C17 1.389(2) . ?
C17 H17 0.9300 . ?
C3 H3 0.9300 . ?
C3 C4 1.391(2) . ?
C42 H42 0.9300 . ?
C42 C41 1.385(2) . ?
C4 H4 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C41 H41 0.9300 . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 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
O22 C21 C8 N13 24.07(14) . . . . ?
O22 C21 C8 N7 166.71(9) . . . . ?
O22 C21 C8 C9 -136.04(11) . . . . ?
O24 C21 C8 N13 -157.52(11) . . . . ?
O24 C21 C8 N7 -14.87(17) . . . . ?
O24 C21 C8 C9 42.37(17) . . . . ?
N13 C8 C9 N7 100.98(12) . . . . ?
N13 C8 C9 C1 -78.1(2) . . . . ?
N34 N38 N37 C36 0.43(13) . . . . ?
N34 C35 C36 N37 -0.01(13) . . . . ?
N34 C35 C36 C39 -176.42(11) . . . . ?
N34 C31 C45 O48 -158.18(11) . . . . ?
N34 C31 C45 O46 22.69(14) . . . . ?
N11 C10 C15 C20 -4.19(17) . . . . ?
N11 C10 C15 C16 175.65(11) . . . . ?
N11 C10 C14 N13 0.55(13) . . . . ?
N33 C32 C25 C30 8.8(2) . . . . ?
N33 C32 C25 C26 -170.45(16) . . . . ?
N33 C32 C31 N34 101.06(11) . . . . ?
N33 C32 C31 C45 -98.54(12) . . . . ?
N33 C31 C45 O48 -15.76(16) . . . . ?
N33 C31 C45 O46 165.12(9) . . . . ?
N7 C8 C9 C1 -179.1(2) . . . . ?
N38 N34 C35 C36 0.28(13) . . . . ?
N38 N34 C31 N33 79.13(13) . . . . ?
N38 N34 C31 C32 22.07(15) . . . . ?
N38 N34 C31 C45 -138.90(11) . . . . ?
N38 N37 C36 C35 -0.26(14) . . . . ?
N38 N37 C36 C39 176.50(10) . . . . ?
N37 C36 C39 C44 -163.09(11) . . . . ?
N37 C36 C39 C40 15.51(17) . . . . ?
N12 N13 C8 N7 119.61(11) . . . . ?
N12 N13 C8 C21 -97.90(13) . . . . ?
N12 N13 C8 C9 62.48(15) . . . . ?
N12 N13 C14 C10 -0.35(13) . . . . ?
N12 N11 C10 C15 179.76(10) . . . . ?
N12 N11 C10 C14 -0.57(13) . . . . ?
C35 N34 N38 N37 -0.45(13) . . . . ?
C35 N34 C31 N33 -92.46(14) . . . . ?
C35 N34 C31 C32 -149.52(11) . . . . ?
C35 N34 C31 C45 49.51(16) . . . . ?
C35 C36 C39 C44 12.86(19) . . . . ?
C35 C36 C39 C40 -168.53(12) . . . . ?
C32 N33 C31 N34 -107.36(11) . . . . ?
C32 N33 C31 C45 109.73(11) . . . . ?
C32 C25 C30 C29 -179.53(11) . . . . ?
C32 C25 C26 C27 178.92(11) . . . . ?
C32 C31 C45 O48 41.07(16) . . . . ?
C32 C31 C45 O46 -138.05(11) . . . . ?
C10 N11 N12 N13 0.34(13) . . . . ?
C10 C15 C20 C19 179.15(11) . . . . ?
C10 C15 C16 C17 -179.60(11) . . . . ?
C15 C10 C14 N13 -179.81(11) . . . . ?
C15 C20 C19 C18 0.60(18) . . . . ?
C15 C16 C17 C18 0.31(18) . . . . ?
C21 C8 C9 N7 -99.45(12) . . . . ?
C21 C8 C9 C1 81.4(2) . . . . ?
C25 C32 C31 N34 -79.9(2) . . . . ?
C25 C32 C31 N33 179.0(2) . . . . ?
C25 C32 C31 C45 80.5(2) . . . . ?
C25 C30 C29 C28 0.82(18) . . . . ?
C25 C26 C27 C28 0.39(18) . . . . ?
C8 N13 N12 N11 177.63(10) . . . . ?
C8 N13 C14 C10 -177.76(11) . . . . ?
C8 N7 C9 C1 179.2(2) . . . . ?
C14 N13 N12 N11 0.02(13) . . . . ?
C14 N13 C8 N7 -63.21(15) . . . . ?
C14 N13 C8 C21 79.28(15) . . . . ?
C14 N13 C8 C9 -120.34(13) . . . . ?
C14 C10 C15 C20 176.21(12) . . . . ?
C14 C10 C15 C16 -3.94(18) . . . . ?
C36 C39 C44 C43 178.70(11) . . . . ?
C36 C39 C40 C41 -178.56(12) . . . . ?
C1 C6 C5 C4 0.71(19) . . . . ?
C1 C2 C3 C4 0.6(2) . . . . ?
C30 C25 C26 C27 -0.36(17) . . . . ?
C30 C29 C28 C27 -0.78(19) . . . . ?
C9 N7 C8 N13 -107.58(12) . . . . ?
C9 N7 C8 C21 109.59(12) . . . . ?
C9 C1 C6 C5 180.00(11) . . . . ?
C9 C1 C2 C3 179.33(12) . . . . ?
C26 C25 C30 C29 -0.25(17) . . . . ?
C26 C27 C28 C29 0.17(19) . . . . ?
C6 C1 C9 N7 -172.78(17) . . . . ?
C6 C1 C9 C8 5.8(3) . . . . ?
C6 C1 C2 C3 -0.25(19) . . . . ?
C6 C5 C4 C3 -0.4(2) . . . . ?
C20 C15 C16 C17 0.25(17) . . . . ?
C20 C19 C18 C17 -0.03(19) . . . . ?
C39 C44 C43 C42 -0.03(19) . . . . ?
C39 C40 C41 C42 -0.3(2) . . . . ?
C44 C39 C40 C41 0.07(19) . . . . ?
C44 C43 C42 C41 -0.15(19) . . . . ?
C16 C15 C20 C19 -0.70(17) . . . . ?
C31 N34 N38 N37 -173.47(10) . . . . ?
C31 N34 C35 C36 172.44(11) . . . . ?
C31 N33 C32 C25 -179.1(2) . . . . ?
C31 C32 C25 C30 -169.63(17) . . . . ?
C31 C32 C25 C26 11.1(3) . . . . ?
C19 C18 C17 C16 -0.42(18) . . . . ?
C43 C42 C41 C40 0.3(2) . . . . ?
C40 C39 C44 C43 0.07(18) . . . . ?
C2 C1 C9 N7 7.6(3) . . . . ?
C2 C1 C9 C8 -173.79(16) . . . . ?
C2 C1 C6 C5 -0.41(18) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C23 O22 C21 O24 -0.38(18) . . . . ?
C23 O22 C21 C8 177.97(10) . . . . ?
C47 O46 C45 O48 2.24(18) . . . . ?
C47 O46 C45 C31 -178.67(11) . . . . ?
