#------------------------------------------------------------------------------
#$Date: 2024-03-04 22:43:28 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290275 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/97/7159790.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_7159790
loop_
_publ_author_name
'Ghatak, Trisha'
'Shah, Chandan'
'Althagafi, Ismail'
'Giri, Nand Gopal'
'Nath, Mahendra'
'Pratap, Ramendra'
_publ_section_title
;
 Iodine/DMSO-mediated one-pot access towards
 1-aryl-2-(pyrazol-5-yl)ethane-1,2-diones via a domino reaction from
 functionalized pent-2-ene-1,5-diones
;
_journal_issue                   9
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              1859
_journal_page_last               1870
_journal_paper_doi               10.1039/D3OB01997G
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C19 H16 N2 O4'
_chemical_formula_sum            'C19 H16 N2 O4'
_chemical_formula_weight         336.34
_chemical_name_systematic        none
_chemical_properties_physical    Moisture-sensitive
_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   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-07-02
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-07-03 deposited with the CCDC.	2024-01-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.107(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3993(5)
_cell_length_b                   19.2977(9)
_cell_length_c                   11.0438(6)
_cell_measurement_reflns_used    7962
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.7950
_cell_measurement_theta_min      3.3050
_cell_volume                     1710.86(17)
_computing_cell_refinement       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.69a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.749
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00  37.00   0.50    3.55    --    5.83 -99.00-120.00  116
  2  ω      2.00  38.00   0.50    3.55    --    5.83 -99.00  30.00   72
  3  ω    -22.00  21.00   0.50    3.55    --    5.83-100.00 111.00   86
  4  ω    -12.00  14.00   0.50    3.55    --    5.83 100.00-143.00   52
  5  ω    -38.00  22.00   0.50    3.55    --   -5.68 100.00-143.00  120
  6  ω     -4.00  62.00   0.50    3.55    --   -5.68  38.00-180.00  132
  7  ω    -23.00  24.00   0.50    3.55    --   -5.68 -99.00  60.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.749
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20045
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.749
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.121
_diffrn_reflns_theta_min         3.301
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.69a (Rigaku Oxford Diffraction, 2022)
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    1.306
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_preparation       none
_exptl_crystal_recrystallization_method none
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     459
_refine_ls_number_reflns         8249
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0492
_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)+(0.0594P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1347
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4665
_reflns_number_total             8249
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01997g2.cif
_cod_data_source_block           gpy-36_auto
_cod_depositor_comments          'Adding full bibliography for 7159790.cif.'
_cod_database_code               7159790
_shelx_shelxl_version_number     2016/4
_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   0.982
_shelx_estimated_absorpt_t_min   0.973
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Me refined with riding coordinates:
 C014(H01J,H01K,H01L), C015(H01A,H01B,H01C), C019(H01M,H01N,H01O), C01E(H01G,
 H01H,H01I)
2.b Aromatic/amide H refined with riding coordinates:
 C00O(H00O), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00W(H00W),
 C00X(H00X), C00Y(H00Y), C010(H010), C011(H011), C012(H012), C013(H013),
 C016(H016), C018(H018), C01A(H01D), C01B(H01E), C01C(H01P), C01D(H01F)
;
_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
;
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
O001 O 0.60113(15) 0.26677(6) 0.59777(13) 0.0589(3) Uani 1 1 d . . . . .
N002 N 0.63745(19) 0.13512(7) 0.73884(14) 0.0470(3) Uani 1 1 d . . . . .
N003 N 0.59913(18) 0.16194(6) 0.83814(13) 0.0461(3) Uani 1 1 d . . . . .
N004 O 0.24396(15) 0.10360(7) 0.91968(13) 0.0637(4) Uani 1 1 d . . . . .
N005 O 0.7185(2) 0.37946(6) 0.02740(12) 0.0711(4) Uani 1 1 d . . . . .
O006 O 0.60125(15) 0.23324(6) 1.09763(13) 0.0585(4) Uani 1 1 d . . . . .
O007 O 0.59162(17) 0.42750(6) 0.61552(12) 0.0573(3) Uani 1 1 d . . . . .
N008 O 0.24377(15) 0.39650(7) 0.41960(13) 0.0640(4) Uani 1 1 d . . . . .
O009 O 0.59157(17) 0.07253(6) 1.11537(12) 0.0575(3) Uani 1 1 d . . . . .
N00A N 0.63801(18) 0.36491(7) 0.23919(14) 0.0468(3) Uani 1 1 d . . . . .
N00B N 0.59904(17) 0.33801(6) 0.33819(13) 0.0461(3) Uani 1 1 d . . . . .
C00C C 0.56717(19) 0.11690(8) 1.03429(16) 0.0417(4) Uani 1 1 d . . . . .
C00D C 0.2003(2) 0.35074(9) 0.49838(17) 0.0497(4) Uani 1 1 d . . . . .
C00E C 0.5004(2) 0.31372(8) 0.56529(15) 0.0420(4) Uani 1 1 d . . . . .
N00F C 0.3275(2) 0.30855(8) 0.57118(16) 0.0447(4) Uani 1 1 d . . . . .
C00G C 0.66883(19) 0.43436(7) 0.24888(15) 0.0406(4) Uani 1 1 d . . . . .
C00H C 0.60755(19) 0.10803(7) 0.91528(15) 0.0398(4) Uani 1 1 d . . . . .
C00I C 0.3275(2) 0.19150(8) 1.07140(16) 0.0455(4) Uani 1 1 d . . . . .
C00J C 0.5005(2) 0.18613(8) 1.06525(15) 0.0425(4) Uani 1 1 d . . . . .
C00K C 0.1997(2) 0.14916(9) 0.99848(17) 0.0493(4) Uani 1 1 d . . . . .
C00L O 0.7187(2) 0.12057(6) 0.52751(12) 0.0715(4) Uani 1 1 d . . . . .
C00M C 0.66855(19) 0.06573(7) 0.74890(15) 0.0402(4) Uani 1 1 d . . . . .
C00N C 0.7265(2) 0.05016(9) 0.53919(17) 0.0532(4) Uani 1 1 d . . . . .
C00O C 0.0400(2) 0.34433(11) 0.5077(2) 0.0673(5) Uani 1 1 d . . . . .
H00O H -0.045276 0.372043 0.458597 0.081 Uiso 1 1 calc R U . . .
C00P C 0.60766(19) 0.39201(8) 0.41540(15) 0.0402(4) Uani 1 1 d . . . . .
C00Q C 0.7055(2) 0.02289(8) 0.65042(16) 0.0461(4) Uani 1 1 d . . . . .
C00R C 0.6512(2) 0.45266(8) 0.36433(15) 0.0433(4) Uani 1 1 d . . . . .
H00R H 0.665464 0.496484 0.400966 0.052 Uiso 1 1 calc R U . . .
C00S C 0.7546(3) 0.49362(11) -0.0518(2) 0.0770(6) Uani 1 1 d . . . . .
H00S H 0.768224 0.475201 -0.125969 0.092 Uiso 1 1 calc R U . . .
C00T C 0.7158(3) 0.54842(9) 0.1666(2) 0.0676(6) Uani 1 1 d . . . . .
H00T H 0.703210 0.567510 0.240549 0.081 Uiso 1 1 calc R U . . .
C00U C 0.2915(2) 0.23878(9) 1.1540(2) 0.0614(5) Uani 1 1 d . . . . .
H00U H 0.375707 0.267016 1.203018 0.074 Uiso 1 1 calc R U . . .
C00V C 0.7057(2) 0.47698(8) 0.15040(16) 0.0460(4) Uani 1 1 d . . . . .
C00W C 0.0403(2) 0.15554(10) 1.0080(2) 0.0661(6) Uani 1 1 d . . . . .
H00W H -0.045063 0.127865 0.958848 0.079 Uiso 1 1 calc R U . . .
C00X C 0.1336(3) 0.24449(11) 1.1643(2) 0.0803(7) Uani 1 1 d . . . . .
H00X H 0.110754 0.276039 1.220711 0.096 Uiso 1 1 calc R U . . .
C00Y C 0.0080(3) 0.29678(12) 0.5901(3) 0.0810(7) Uani 1 1 d . . . . .
H00Y H -0.099779 0.292218 0.595713 0.097 Uiso 1 1 calc R U . . .
C00Z C 0.56705(19) 0.38305(8) 0.53423(16) 0.0415(4) Uani 1 1 d . . . . .
C010 C 0.0085(3) 0.20306(12) 1.0905(2) 0.0800(7) Uani 1 1 d . . . . .
H010 H -0.099106 0.207395 1.096679 0.096 Uiso 1 1 calc R U . . .
C011 C 0.7546(3) 0.00608(11) 0.4486(2) 0.0760(6) Uani 1 1 d . . . . .
H011 H 0.768587 0.024375 0.374439 0.091 Uiso 1 1 calc R U . . .
C012 C 0.6512(2) 0.04735(8) 0.86427(15) 0.0441(4) Uani 1 1 d . . . . .
H012 H 0.665469 0.003512 0.900884 0.053 Uiso 1 1 calc R U . . .
C013 C 0.7621(3) -0.06369(11) 0.4670(2) 0.0830(7) Uani 1 1 d . . . . .
H013 H 0.779786 -0.092581 0.404781 0.100 Uiso 1 1 calc R U . . .
C014 C 0.7238(4) 0.15084(11) 0.4112(2) 0.0957(9) Uani 1 1 d . . . . .
H01J H 0.717265 0.200349 0.416746 0.143 Uiso 1 1 calc R U . . .
H01K H 0.826118 0.138330 0.394782 0.143 Uiso 1 1 calc R U . . .
H01L H 0.631365 0.134255 0.343556 0.143 Uiso 1 1 calc R U . . .
C015 C 0.7231(4) 0.34911(12) -0.0896(2) 0.0965(9) Uani 1 1 d . . . . .
H01A H 0.716443 0.299601 -0.084135 0.145 Uiso 1 1 calc R U . . .
H01B H 0.630559 0.365769 -0.157057 0.145 Uiso 1 1 calc R U . . .
H01C H 0.825325 0.361586 -0.106196 0.145 Uiso 1 1 calc R U . . .
C016 C 0.7161(3) -0.04844(9) 0.6665(2) 0.0679(6) Uani 1 1 d . . . . .
H016 H 0.703999 -0.067563 0.740643 0.082 Uiso 1 1 calc R U . . .
C017 C 0.7266(2) 0.45003(9) 0.03905(17) 0.0550(5) Uani 1 1 d . . . . .
C018 C 0.7440(3) 0.59173(10) 0.0756(2) 0.0828(7) Uani 1 1 d . . . . .
H018 H 0.750399 0.639421 0.088243 0.099 Uiso 1 1 calc R U . . .
C019 C 0.1213(3) 0.05764(11) 0.8448(2) 0.0718(6) Uani 1 1 d . . . . .
H01M H 0.170589 0.028928 0.794591 0.108 Uiso 1 1 calc R U . . .
H01N H 0.078829 0.028994 0.899367 0.108 Uiso 1 1 calc R U . . .
H01O H 0.031827 0.084020 0.790172 0.108 Uiso 1 1 calc R U . . .
C01A C 0.2917(2) 0.26130(9) 0.6541(2) 0.0613(5) Uani 1 1 d . . . . .
H01D H 0.376034 0.233146 0.703204 0.074 Uiso 1 1 calc R U . . .
C01B C 0.7624(3) 0.56394(11) -0.0331(2) 0.0836(7) Uani 1 1 d . . . . .
H01E H 0.780485 0.592948 -0.094977 0.100 Uiso 1 1 calc R U . . .
C01C C 0.7440(3) -0.09180(11) 0.5753(2) 0.0834(7) Uani 1 1 d . . . . .
H01P H 0.750390 -0.139505 0.587669 0.100 Uiso 1 1 calc R U . . .
C01D C 0.1336(3) 0.25550(12) 0.6648(2) 0.0798(7) Uani 1 1 d . . . . .
H01F H 0.111026 0.224195 0.721670 0.096 Uiso 1 1 calc R U . . .
C01E C 0.1215(3) 0.44210(11) 0.3447(2) 0.0714(6) Uani 1 1 d . . . . .
H01G H 0.170845 0.470909 0.294677 0.107 Uiso 1 1 calc R U . . .
H01H H 0.032432 0.415594 0.289877 0.107 Uiso 1 1 calc R U . . .
H01I H 0.078401 0.470658 0.399033 0.107 Uiso 1 1 calc R U . . .
H00A H 0.643(2) 0.3363(9) 0.1783(19) 0.056(5) Uiso 1 1 d . . . . .
H002 H 0.642(2) 0.1615(10) 0.678(2) 0.062(6) Uiso 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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N003 N002 C00M 113.62(14) . . ?
N003 N002 H002 119.6(13) . . ?
C00M N002 H002 126.8(13) . . ?
C00H N003 N002 104.02(12) . . ?
C00K N004 C019 119.03(14) . . ?
C017 N005 C015 118.63(15) . . ?
C00D N008 C01E 119.32(14) . . ?
N00B N00A C00G 113.86(13) . . ?
N00B N00A H00A 117.4(12) . . ?
C00G N00A H00A 128.8(12) . . ?
C00P N00B N00A 103.85(12) . . ?
O009 C00C C00H 123.26(14) . . ?
O009 C00C C00J 116.51(14) . . ?
C00H C00C C00J 120.13(14) . . ?
N008 C00D N00F 116.27(14) . . ?
N008 C00D C00O 123.65(17) . . ?
C00O C00D N00F 120.08(16) . . ?
O001 C00E N00F 122.91(14) . . ?
O001 C00E C00Z 116.65(14) . . ?
N00F C00E C00Z 119.95(13) . . ?
C00D N00F C00E 122.14(14) . . ?
C01A N00F C00D 119.11(15) . . ?
C01A N00F C00E 118.73(16) . . ?
N00A C00G C00R 104.83(13) . . ?
N00A C00G C00V 124.71(14) . . ?
C00R C00G C00V 130.42(14) . . ?
N003 C00H C00C 120.05(13) . . ?
N003 C00H C012 111.59(14) . . ?
C012 C00H C00C 128.32(14) . . ?
C00K C00I C00J 122.03(13) . . ?
C00U C00I C00J 118.98(14) . . ?
C00U C00I C00K 118.97(15) . . ?
O006 C00J C00C 116.65(14) . . ?
O006 C00J C00I 122.70(14) . . ?
C00I C00J C00C 120.16(12) . . ?
N004 C00K C00I 115.90(14) . . ?
N004 C00K C00W 124.00(15) . . ?
C00W C00K C00I 120.10(15) . . ?
C00N C00L C014 118.73(14) . . ?
N002 C00M C00Q 124.71(15) . . ?
N002 C00M C012 105.06(13) . . ?
C012 C00M C00Q 130.19(15) . . ?
C00L C00N C00Q 116.37(14) . . ?
C00L C00N C011 123.81(17) . . ?
C011 C00N C00Q 119.81(17) . . ?
C00D C00O H00O 120.2 . . ?
C00Y C00O C00D 119.51(19) . . ?
C00Y C00O H00O 120.2 . . ?
N00B C00P C00R 111.61(14) . . ?
N00B C00P C00Z 119.91(13) . . ?
C00R C00P C00Z 128.43(13) . . ?
C00N C00Q C00M 123.25(15) . . ?
C016 C00Q C00M 118.84(16) . . ?
C016 C00Q C00N 117.89(15) . . ?
C00G C00R C00P 105.83(13) . . ?
C00G C00R H00R 127.1 . . ?
C00P C00R H00R 127.1 . . ?
C017 C00S H00S 119.9 . . ?
C01B C00S H00S 119.9 . . ?
C01B C00S C017 120.22(19) . . ?
C00V C00T H00T 119.2 . . ?
C018 C00T H00T 119.2 . . ?
C018 C00T C00V 121.62(19) . . ?
C00I C00U H00U 119.6 . . ?
C00X C00U C00I 120.84(17) . . ?
C00X C00U H00U 119.6 . . ?
C00T C00V C00G 118.61(15) . . ?
C00T C00V C017 117.72(16) . . ?
C017 C00V C00G 123.64(14) . . ?
C00K C00W H00W 120.2 . . ?
C010 C00W C00K 119.53(17) . . ?
C010 C00W H00W 120.2 . . ?
C00U C00X H00X 120.3 . . ?
C00U C00X C010 119.46(17) . . ?
C010 C00X H00X 120.3 . . ?
C00O C00Y H00Y 119.4 . . ?
C00O C00Y C01D 121.10(18) . . ?
C01D C00Y H00Y 119.4 . . ?
O007 C00Z C00E 116.51(14) . . ?
O007 C00Z C00P 123.16(14) . . ?
C00P C00Z C00E 120.22(13) . . ?
C00W C010 C00X 121.09(18) . . ?
C00W C010 H010 119.5 . . ?
C00X C010 H010 119.5 . . ?
C00N C011 H011 119.7 . . ?
C013 C011 C00N 120.64(19) . . ?
C013 C011 H011 119.7 . . ?
C00H C012 H012 127.1 . . ?
C00M C012 C00H 105.70(14) . . ?
C00M C012 H012 127.1 . . ?
C011 C013 H013 119.6 . . ?
C011 C013 C01C 120.89(18) . . ?
C01C C013 H013 119.6 . . ?
C00L C014 H01J 109.5 . . ?
C00L C014 H01K 109.5 . . ?
C00L C014 H01L 109.5 . . ?
H01J C014 H01K 109.5 . . ?
H01J C014 H01L 109.5 . . ?
H01K C014 H01L 109.5 . . ?
N005 C015 H01A 109.5 . . ?
N005 C015 H01B 109.5 . . ?
N005 C015 H01C 109.5 . . ?
H01A C015 H01B 109.5 . . ?
H01A C015 H01C 109.5 . . ?
H01B C015 H01C 109.5 . . ?
C00Q C016 H016 119.2 . . ?
C01C C016 C00Q 121.68(19) . . ?
C01C C016 H016 119.2 . . ?
N005 C017 C00S 123.50(16) . . ?
N005 C017 C00V 116.05(15) . . ?
C00S C017 C00V 120.44(17) . . ?
C00T C018 H018 120.3 . . ?
C01B C018 C00T 119.38(19) . . ?
C01B C018 H018 120.3 . . ?
N004 C019 H01M 109.5 . . ?
N004 C019 H01N 109.5 . . ?
N004 C019 H01O 109.5 . . ?
H01M C019 H01N 109.5 . . ?
H01M C019 H01O 109.5 . . ?
H01N C019 H01O 109.5 . . ?
N00F C01A H01D 119.5 . . ?
C01D C01A N00F 120.92(18) . . ?
C01D C01A H01D 119.5 . . ?
C00S C01B H01E 119.7 . . ?
C018 C01B C00S 120.61(19) . . ?
C018 C01B H01E 119.7 . . ?
C013 C01C C016 119.1(2) . . ?
C013 C01C H01P 120.5 . . ?
C016 C01C H01P 120.5 . . ?
C00Y C01D H01F 120.4 . . ?
C01A C01D C00Y 119.25(19) . . ?
C01A C01D H01F 120.4 . . ?
N008 C01E H01G 109.5 . . ?
N008 C01E H01H 109.5 . . ?
N008 C01E H01I 109.5 . . ?
H01G C01E H01H 109.5 . . ?
H01G C01E H01I 109.5 . . ?
H01H C01E H01I 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
O001 C00E 1.2193(19) . ?
N002 N003 1.3349(18) . ?
N002 C00M 1.363(2) . ?
N002 H002 0.85(2) . ?
N003 C00H 1.333(2) . ?
N004 C00K 1.3634(19) . ?
N004 C019 1.425(2) . ?
N005 C015 1.429(2) . ?
N005 C017 1.368(2) . ?
O006 C00J 1.2219(17) . ?
O007 C00Z 1.2146(18) . ?
N008 C00D 1.363(2) . ?
N008 C01E 1.419(2) . ?
O009 C00C 1.212(2) . ?
N00A N00B 1.3351(18) . ?
N00A C00G 1.3634(19) . ?
N00A H00A 0.880(18) . ?
N00B C00P 1.3348(18) . ?
C00C C00H 1.461(2) . ?
C00C C00J 1.526(2) . ?
C00D N00F 1.395(2) . ?
C00D C00O 1.386(2) . ?
C00E N00F 1.476(2) . ?
C00E C00Z 1.528(2) . ?
N00F C01A 1.387(2) . ?
C00G C00R 1.372(2) . ?
C00G C00V 1.467(2) . ?
C00H C012 1.394(2) . ?
C00I C00J 1.478(2) . ?
C00I C00K 1.400(2) . ?
C00I C00U 1.385(2) . ?
C00K C00W 1.379(2) . ?
C00L C00N 1.364(2) . ?
C00L C014 1.423(2) . ?
C00M C00Q 1.470(2) . ?
C00M C012 1.371(2) . ?
C00N C00Q 1.394(2) . ?
C00N C011 1.386(2) . ?
C00O H00O 0.9300 . ?
C00O C00Y 1.373(3) . ?
C00P C00R 1.394(2) . ?
C00P C00Z 1.460(2) . ?
C00Q C016 1.387(2) . ?
C00R H00R 0.9300 . ?
C00S H00S 0.9300 . ?
C00S C017 1.382(3) . ?
C00S C01B 1.372(3) . ?
C00T H00T 0.9300 . ?
C00T C00V 1.389(2) . ?
C00T C018 1.380(3) . ?
C00U H00U 0.9300 . ?
C00U C00X 1.369(3) . ?
C00V C017 1.393(2) . ?
C00W H00W 0.9300 . ?
C00W C010 1.373(3) . ?
C00X H00X 0.9300 . ?
C00X C010 1.380(3) . ?
C00Y H00Y 0.9300 . ?
C00Y C01D 1.384(3) . ?
C010 H010 0.9300 . ?
C011 H011 0.9300 . ?
C011 C013 1.360(3) . ?
C012 H012 0.9300 . ?
C013 H013 0.9300 . ?
C013 C01C 1.362(3) . ?
C014 H01J 0.9600 . ?
C014 H01K 0.9600 . ?
C014 H01L 0.9600 . ?
C015 H01A 0.9600 . ?
C015 H01B 0.9600 . ?
C015 H01C 0.9600 . ?
C016 H016 0.9300 . ?
C016 C01C 1.382(3) . ?
C018 H018 0.9300 . ?
C018 C01B 1.364(3) . ?
C019 H01M 0.9600 . ?
C019 H01N 0.9600 . ?
C019 H01O 0.9600 . ?
C01A H01D 0.9300 . ?
C01A C01D 1.372(3) . ?
C01B H01E 0.9300 . ?
C01C H01P 0.9300 . ?
C01D H01F 0.9300 . ?
C01E H01G 0.9600 . ?
C01E H01H 0.9600 . ?
C01E H01I 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
O001 C00E N00F C00D -158.59(17) . . . . ?
O001 C00E N00F C01A 23.0(2) . . . . ?
O001 C00E C00Z O007 -101.16(18) . . . . ?
O001 C00E C00Z C00P 75.1(2) . . . . ?
N002 N003 C00H C00C -177.89(14) . . . . ?
N002 N003 C00H C012 -0.02(18) . . . . ?
N002 C00M C00Q C00N 5.5(3) . . . . ?
N002 C00M C00Q C016 -172.70(18) . . . . ?
N002 C00M C012 C00H 0.89(18) . . . . ?
N003 N002 C00M C00Q 176.89(15) . . . . ?
N003 N002 C00M C012 -0.99(19) . . . . ?
N003 C00H C012 C00M -0.57(19) . . . . ?
N004 C00K C00W C010 179.9(2) . . . . ?
N008 C00D N00F C00E 1.0(2) . . . . ?
N008 C00D N00F C01A 179.41(16) . . . . ?
N008 C00D C00O C00Y -179.9(2) . . . . ?
O009 C00C C00H N003 -170.72(15) . . . . ?
O009 C00C C00H C012 11.8(3) . . . . ?
O009 C00C C00J O006 101.33(18) . . . . ?
O009 C00C C00J C00I -70.8(2) . . . . ?
N00A N00B C00P C00R 0.28(18) . . . . ?
N00A N00B C00P C00Z 178.02(15) . . . . ?
N00A C00G C00R C00P -0.99(18) . . . . ?
N00A C00G C00V C00T 172.70(17) . . . . ?
N00A C00G C00V C017 -5.4(3) . . . . ?
N00B N00A C00G C00R 1.26(19) . . . . ?
N00B N00A C00G C00V -176.67(15) . . . . ?
N00B C00P C00R C00G 0.47(19) . . . . ?
N00B C00P C00Z O007 170.73(15) . . . . ?
N00B C00P C00Z C00E -5.3(2) . . . . ?
C00C C00H C012 C00M 177.08(15) . . . . ?
C00D N00F C01A C01D 0.3(3) . . . . ?
C00D C00O C00Y C01D 0.6(4) . . . . ?
C00E N00F C01A C01D 178.74(19) . . . . ?
N00F C00D C00O C00Y 0.7(3) . . . . ?
N00F C00E C00Z O007 71.0(2) . . . . ?
N00F C00E C00Z C00P -112.73(17) . . . . ?
N00F C01A C01D C00Y 1.0(3) . . . . ?
C00G N00A N00B C00P -0.96(19) . . . . ?
C00G C00V C017 N005 -2.9(3) . . . . ?
C00G C00V C017 C00S 177.45(19) . . . . ?
C00H C00C C00J O006 -75.1(2) . . . . ?
C00H C00C C00J C00I 112.73(17) . . . . ?
C00I C00K C00W C010 -0.8(3) . . . . ?
C00I C00U C00X C010 -0.7(4) . . . . ?
C00J C00C C00H N003 5.4(2) . . . . ?
C00J C00C C00H C012 -172.02(15) . . . . ?
C00J C00I C00K N004 -1.2(3) . . . . ?
C00J C00I C00K C00W 179.47(18) . . . . ?
C00J C00I C00U C00X -178.8(2) . . . . ?
C00K C00I C00J O006 158.57(18) . . . . ?
C00K C00I C00J C00C -29.7(2) . . . . ?
C00K C00I C00U C00X -0.2(3) . . . . ?
C00K C00W C010 C00X -0.1(4) . . . . ?
C00L C00N C00Q C00M 3.0(3) . . . . ?
C00L C00N C00Q C016 -178.73(17) . . . . ?
C00L C00N C011 C013 179.5(2) . . . . ?
C00M N002 N003 C00H 0.63(19) . . . . ?
C00M C00Q C016 C01C 177.4(2) . . . . ?
C00N C00Q C016 C01C -0.9(3) . . . . ?
C00N C011 C013 C01C -0.8(4) . . . . ?
C00O C00D N00F C00E -179.56(16) . . . . ?
C00O C00D N00F C01A -1.1(3) . . . . ?
C00O C00Y C01D C01A -1.5(4) . . . . ?
C00Q C00M C012 C00H -176.83(16) . . . . ?
C00Q C00N C011 C013 0.0(3) . . . . ?
C00Q C016 C01C C013 0.2(4) . . . . ?
C00R C00G C00V C00T -4.7(3) . . . . ?
C00R C00G C00V C017 177.26(18) . . . . ?
C00R C00P C00Z O007 -11.9(3) . . . . ?
C00R C00P C00Z C00E 172.05(16) . . . . ?
C00T C00V C017 N005 178.97(17) . . . . ?
C00T C00V C017 C00S -0.6(3) . . . . ?
C00T C018 C01B C00S -0.6(4) . . . . ?
C00U C00I C00J O006 -22.9(3) . . . . ?
C00U C00I C00J C00C 148.76(17) . . . . ?
C00U C00I C00K N004 -179.71(17) . . . . ?
C00U C00I C00K C00W 1.0(3) . . . . ?
C00U C00X C010 C00W 0.9(4) . . . . ?
C00V C00G C00R C00P 176.79(16) . . . . ?
C00V C00T C018 C01B 0.0(4) . . . . ?
C00Z C00E N00F C00D 29.7(2) . . . . ?
C00Z C00E N00F C01A -148.68(16) . . . . ?
C00Z C00P C00R C00G -177.03(16) . . . . ?
C011 C00N C00Q C00M -177.47(18) . . . . ?
C011 C00N C00Q C016 0.8(3) . . . . ?
C011 C013 C01C C016 0.7(4) . . . . ?
C012 C00M C00Q C00N -177.13(18) . . . . ?
C012 C00M C00Q C016 4.6(3) . . . . ?
C014 C00L C00N C00Q -174.3(2) . . . . ?
C014 C00L C00N C011 6.2(3) . . . . ?
C015 N005 C017 C00S -6.3(3) . . . . ?
C015 N005 C017 C00V 174.1(2) . . . . ?
C017 C00S C01B C018 0.5(4) . . . . ?
C018 C00T C00V C00G -177.6(2) . . . . ?
C018 C00T C00V C017 0.6(3) . . . . ?
C019 N004 C00K C00I 178.46(18) . . . . ?
C019 N004 C00K C00W -2.2(3) . . . . ?
C01B C00S C017 N005 -179.5(2) . . . . ?
C01B C00S C017 C00V 0.1(4) . . . . ?
C01E N008 C00D N00F -178.64(16) . . . . ?
C01E N008 C00D C00O 1.9(3) . . . . ?
