#------------------------------------------------------------------------------
#$Date: 2022-07-06 11:28:44 +0300 (Wed, 06 Jul 2022) $
#$Revision: 276666 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/15/7061555.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_7061555
loop_
_publ_author_name
'Wang, Yu'
'Xu, Yaoyao'
'Khan, Shahid'
'Zhang, Zhunjie'
'Khan, Ajmal'
_publ_section_title
;
 Selective approach to N-substituted tertiary 2-pyridones
;
_journal_issue                   23
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              11138
_journal_page_last               11142
_journal_paper_doi               10.1039/D2NJ01065H
_journal_volume                  46
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C10 H12 N2 O4'
_chemical_formula_sum            'C10 H12 N2 O4'
_chemical_formula_weight         224.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-03
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_audit_update_record
;
2022-02-12 deposited with the CCDC.	2022-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.332(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9511(8)
_cell_length_b                   7.5328(6)
_cell_length_c                   12.7907(9)
_cell_measurement_reflns_used    4384
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      30.37
_cell_measurement_theta_min      2.27
_cell_volume                     1041.17(13)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'Bruker BIS V6.2.1'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON 100'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE TXS PHOTON 100'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12389
_diffrn_reflns_point_group_measured_fraction_full 0.872
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.526
_diffrn_reflns_theta_min         2.274
_diffrn_source                   TXS
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_type              'Rotaing Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1707 before and 0.0821 after correction.
The Ratio of minimum to maximum transmission is 0.9283.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1128 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.1(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         5296
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0489
_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)+(0.0476P)²+0.3199P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1234
_reflns_Friedel_coverage         0.566
_reflns_Friedel_fraction_full    0.728
_reflns_Friedel_fraction_max     0.646
_reflns_number_gt                4197
_reflns_number_total             5296
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj01065h2.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7061555.cif.
;
_cod_database_code               7061555
_shelx_shelxl_version_number     2018/3
_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   0.989
_shelx_estimated_absorpt_t_min   0.986
_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, All O(H) groups
2. Others
 Sof(O4A)=Sof(H4A)=Sof(H9BD)=Sof(H9BE)=Sof(H10C)=Sof(H10D)=Sof(H10E)=1-FVAR(1)
 Sof(O4)=Sof(H4)=Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=Sof(H10A)=Sof(H10B)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C9(H9BD,H9BE), C10(H10A,H10B), C20(H20A,H20B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C7(H7), C12(H12), C13(H13), C15(H15), C17(H17)
3.c X=CH2 refined with riding coordinates:
 C8(H8A,H8B), C18(H18A,H18B)
3.d Idealised Me refined as rotating group:
 C9(H9AA,H9AB,H9AC), C10(H10C,H10D,H10E), C19(H19A,H19B,H19C)
3.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O4A(H4A), O8(H8)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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
O1 O -0.67717(19) -0.6373(5) -0.3248(2) 0.0502(8) Uani 1 1 d . . . . .
O2 O -0.5610(2) -0.4259(4) -0.36715(19) 0.0367(6) Uani 1 1 d . . . . .
O3 O -0.2242(2) -1.0514(4) -0.4224(2) 0.0392(6) Uani 1 1 d . . . . .
O4 O -0.2460(2) -0.6700(4) -0.61122(19) 0.0343(7) Uani 0.815(5) 1 d . . P A 1
H4 H -0.255900 -0.561239 -0.600743 0.051 Uiso 0.815(5) 1 calc R U P A 1
O4A O -0.2268(12) -0.396(2) -0.4639(10) 0.036(3) Uani 0.185(5) 1 d . . P A 2
H4A H -0.228596 -0.430327 -0.526557 0.054 Uiso 0.185(5) 1 calc R U P A 2
N1 N -0.5820(2) -0.5845(5) -0.3537(2) 0.0331(7) Uani 1 1 d . . . . .
N2 N -0.2869(2) -0.7645(4) -0.40230(19) 0.0250(6) Uani 1 1 d . . . . .
C1 C -0.4914(3) -0.7133(5) -0.3718(2) 0.0263(7) Uani 1 1 d . . . . .
C2 C -0.5158(3) -0.8972(6) -0.3683(2) 0.0323(8) Uani 1 1 d . . . . .
H2 H -0.593832 -0.939465 -0.355626 0.039 Uiso 1 1 calc R U . . .
C3 C -0.4257(3) -1.0105(5) -0.3832(2) 0.0355(8) Uani 1 1 d . . . . .
H3 H -0.441239 -1.134321 -0.379995 0.043 Uiso 1 1 calc R U . . .
C4 C -0.3054(3) -0.9522(5) -0.4040(2) 0.0294(7) Uani 1 1 d . . . . .
C5 C -0.3785(2) -0.6526(5) -0.3886(2) 0.0260(6) Uani 1 1 d . . . . .
H5 H -0.364454 -0.528302 -0.390587 0.031 Uiso 1 1 calc R U . . .
C6 C -0.1621(3) -0.6941(5) -0.4200(2) 0.0259(6) Uani 1 1 d . . . . .
C7 C -0.0631(3) -0.7819(6) -0.3400(3) 0.0381(8) Uani 1 1 d . . . . .
H7 H -0.088440 -0.831516 -0.278610 0.046 Uiso 1 1 calc R U . . .
C8 C 0.0538(3) -0.7952(7) -0.3481(3) 0.0467(10) Uani 1 1 d . . . . .
H8A H 0.083154 -0.747461 -0.408125 0.056 Uiso 1 1 calc R U . . .
H8B H 0.109597 -0.852633 -0.293938 0.056 Uiso 1 1 calc R U . . .
C9 C -0.1549(3) -0.4954(5) -0.4013(3) 0.0368(8) Uani 1 1 d . . . . .
H9AA H -0.224913 -0.437302 -0.445739 0.055 Uiso 0.815(5) 1 calc R U P A 1
H9AB H -0.077231 -0.449760 -0.419483 0.055 Uiso 0.815(5) 1 calc R U P A 1
H9AC H -0.158019 -0.470537 -0.326556 0.055 Uiso 0.815(5) 1 calc R U P A 1
H9BD H -0.170946 -0.472848 -0.328469 0.044 Uiso 0.185(5) 1 calc R U P A 2
H9BE H -0.068872 -0.457449 -0.403688 0.044 Uiso 0.185(5) 1 calc R U P A 2
C10 C -0.1468(3) -0.7359(5) -0.5348(2) 0.0319(7) Uani 1 1 d . . . . .
H10C H -0.217700 -0.805897 -0.568805 0.048 Uiso 0.185(5) 1 calc R U P A 2
H10D H -0.070478 -0.803799 -0.534862 0.048 Uiso 0.185(5) 1 calc R U P A 2
H10E H -0.142484 -0.624778 -0.573807 0.048 Uiso 0.185(5) 1 calc R U P A 2
H10A H -0.068176 -0.683494 -0.548822 0.038 Uiso 0.815(5) 1 calc R U P A 1
H10B H -0.141197 -0.866195 -0.543114 0.038 Uiso 0.815(5) 1 calc R U P A 1
O5 O -0.6768(2) -0.8421(5) -0.8162(2) 0.0541(9) Uani 1 1 d . . . . .
O6 O -0.5661(2) -1.0612(4) -0.86085(19) 0.0398(7) Uani 1 1 d . . . . .
O7 O -0.2178(2) -0.4473(3) -0.9192(2) 0.0387(6) Uani 1 1 d . . . . .
O8 O -0.2346(2) -1.0987(3) -0.96624(19) 0.0350(5) Uani 1 1 d . . . . .
H8 H -0.232590 -1.206614 -0.949609 0.053 Uiso 1 1 calc R U . . .
N3 N -0.5843(2) -0.9015(5) -0.8476(2) 0.0347(7) Uani 1 1 d . . . . .
N4 N -0.2871(2) -0.7301(4) -0.8991(2) 0.0238(5) Uani 1 1 d . . . . .
C11 C -0.4918(3) -0.7739(5) -0.8683(2) 0.0296(7) Uani 1 1 d . . . . .
C12 C -0.5148(3) -0.5926(6) -0.8689(2) 0.0343(8) Uani 1 1 d . . . . .
H12 H -0.592970 -0.547821 -0.858290 0.041 Uiso 1 1 calc R U . . .
C13 C -0.4225(3) -0.4817(5) -0.8850(2) 0.0336(8) Uani 1 1 d . . . . .
H13 H -0.436927 -0.357396 -0.884618 0.040 Uiso 1 1 calc R U . . .
C14 C -0.3035(3) -0.5442(5) -0.9028(2) 0.0284(7) Uani 1 1 d . . . . .
C15 C -0.3797(3) -0.8399(5) -0.8833(2) 0.0245(6) Uani 1 1 d . . . . .
H15 H -0.366893 -0.964655 -0.882630 0.029 Uiso 1 1 calc R U . . .
C16 C -0.1615(3) -0.8028(5) -0.9132(2) 0.0254(6) Uani 1 1 d . . . . .
C17 C -0.0664(3) -0.7176(5) -0.8291(3) 0.0313(7) Uani 1 1 d . . . . .
H17 H -0.093819 -0.676005 -0.766670 0.038 Uiso 1 1 calc R U . . .
C18 C 0.0508(3) -0.6967(6) -0.8358(3) 0.0419(9) Uani 1 1 d . . . . .
H18A H 0.081733 -0.736601 -0.896922 0.050 Uiso 1 1 calc R U . . .
H18B H 0.104932 -0.641801 -0.779472 0.050 Uiso 1 1 calc R U . . .
C19 C -0.1422(3) -0.7699(5) -1.0275(2) 0.0327(7) Uani 1 1 d . . . . .
H19A H -0.138509 -0.641878 -1.040202 0.049 Uiso 1 1 calc R U . . .
H19B H -0.211295 -0.821520 -1.076388 0.049 Uiso 1 1 calc R U . . .
H19C H -0.064578 -0.825296 -1.039138 0.049 Uiso 1 1 calc R U . . .
C20 C -0.1538(3) -1.0020(5) -0.8889(3) 0.0281(7) Uani 1 1 d . . . . .
H20A H -0.067818 -1.043464 -0.887699 0.034 Uiso 1 1 calc R U . . .
H20B H -0.176301 -1.023717 -0.818135 0.034 Uiso 1 1 calc R U . . .
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
C10 O4 H4 109.5 . . ?
C9 O4A H4A 109.5 . . ?
O1 N1 O2 122.9(3) . . ?
O1 N1 C1 118.3(4) . . ?
O2 N1 C1 118.9(3) . . ?
C4 N2 C6 118.2(3) . . ?
C5 N2 C4 121.1(3) . . ?
C5 N2 C6 120.7(3) . . ?
C2 C1 N1 121.3(3) . . ?
C5 C1 N1 117.8(3) . . ?
C5 C1 C2 120.9(3) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 118.6 . . ?
C2 C3 C4 122.9(3) . . ?
C4 C3 H3 118.6 . . ?
O3 C4 N2 120.4(3) . . ?
O3 C4 C3 124.3(4) . . ?
N2 C4 C3 115.3(3) . . ?
N2 C5 C1 121.6(3) . . ?
N2 C5 H5 119.2 . . ?
C1 C5 H5 119.2 . . ?
N2 C6 C7 108.0(3) . . ?
N2 C6 C10 108.2(2) . . ?
C7 C6 C10 112.3(3) . . ?
C9 C6 N2 110.3(3) . . ?
C9 C6 C7 108.1(3) . . ?
C9 C6 C10 110.0(3) . . ?
C6 C7 H7 117.2 . . ?
C8 C7 C6 125.6(4) . . ?
C8 C7 H7 117.2 . . ?
C7 C8 H8A 120.0 . . ?
C7 C8 H8B 120.0 . . ?
H8A C8 H8B 120.0 . . ?
O4A C9 C6 118.2(8) . . ?
O4A C9 H9BD 107.8 . . ?
O4A C9 H9BE 107.8 . . ?
C6 C9 H9AA 109.5 . . ?
C6 C9 H9AB 109.5 . . ?
C6 C9 H9AC 109.5 . . ?
C6 C9 H9BD 107.8 . . ?
C6 C9 H9BE 107.8 . . ?
H9AA C9 H9AB 109.5 . . ?
H9AA C9 H9AC 109.5 . . ?
H9AB C9 H9AC 109.5 . . ?
H9BD C9 H9BE 107.1 . . ?
O4 C10 C6 113.2(2) . . ?
O4 C10 H10A 108.9 . . ?
O4 C10 H10B 108.9 . . ?
C6 C10 H10C 109.5 . . ?
C6 C10 H10D 109.5 . . ?
C6 C10 H10E 109.5 . . ?
C6 C10 H10A 108.9 . . ?
C6 C10 H10B 108.9 . . ?
H10C C10 H10D 109.5 . . ?
H10C C10 H10E 109.5 . . ?
H10D C10 H10E 109.5 . . ?
H10A C10 H10B 107.7 . . ?
C20 O8 H8 109.5 . . ?
O5 N3 O6 123.8(3) . . ?
O5 N3 C11 117.0(4) . . ?
O6 N3 C11 119.2(3) . . ?
C14 N4 C16 117.8(3) . . ?
C15 N4 C14 121.2(3) . . ?
C15 N4 C16 120.9(3) . . ?
C12 C11 N3 121.4(3) . . ?
C15 C11 N3 117.0(3) . . ?
C15 C11 C12 121.6(3) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 C11 117.9(3) . . ?
C13 C12 H12 121.0 . . ?
C12 C13 H13 118.6 . . ?
C12 C13 C14 122.7(4) . . ?
C14 C13 H13 118.6 . . ?
O7 C14 N4 119.7(3) . . ?
O7 C14 C13 124.6(3) . . ?
N4 C14 C13 115.7(3) . . ?
N4 C15 C11 120.8(3) . . ?
N4 C15 H15 119.6 . . ?
C11 C15 H15 119.6 . . ?
N4 C16 C19 108.8(2) . . ?
N4 C16 C20 110.5(2) . . ?
C17 C16 N4 107.2(3) . . ?
C17 C16 C19 115.1(3) . . ?
C17 C16 C20 105.2(3) . . ?
C20 C16 C19 109.9(3) . . ?
C16 C17 H17 117.5 . . ?
C18 C17 C16 125.0(3) . . ?
C18 C17 H17 117.5 . . ?
C17 C18 H18A 120.0 . . ?
C17 C18 H18B 120.0 . . ?
H18A C18 H18B 120.0 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O8 C20 C16 110.8(3) . . ?
O8 C20 H20A 109.5 . . ?
O8 C20 H20B 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
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
O1 N1 1.227(3) . ?
O2 N1 1.233(4) . ?
O3 C4 1.214(4) . ?
O4 H4 0.8400 . ?
O4 C10 1.428(4) . ?
O4A H4A 0.8400 . ?
O4A C9 1.273(14) . ?
N1 C1 1.434(5) . ?
N2 C4 1.428(5) . ?
N2 C5 1.343(4) . ?
N2 C6 1.517(4) . ?
C1 C2 1.413(5) . ?
C1 C5 1.367(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.341(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.454(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.517(5) . ?
C6 C9 1.516(5) . ?
C6 C10 1.537(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.306(4) . ?
C8 H8A 0.9500 . ?
C8 H8B 0.9500 . ?
C9 H9AA 0.9800 . ?
C9 H9AB 0.9800 . ?
C9 H9AC 0.9800 . ?
C9 H9BD 0.9900 . ?
C9 H9BE 0.9900 . ?
C10 H10C 0.9800 . ?
C10 H10D 0.9800 . ?
C10 H10E 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
O5 N3 1.233(4) . ?
O6 N3 1.236(5) . ?
O7 C14 1.234(4) . ?
O8 H8 0.8400 . ?
O8 C20 1.417(4) . ?
N3 C11 1.451(5) . ?
N4 C14 1.412(4) . ?
N4 C15 1.349(4) . ?
N4 C16 1.518(4) . ?
C11 C12 1.389(6) . ?
C11 C15 1.366(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.352(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.438(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.514(5) . ?
C16 C19 1.531(4) . ?
C16 C20 1.531(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.310(4) . ?
C18 H18A 0.9500 . ?
C18 H18B 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
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
O1 N1 C1 C2 6.9(4) . . . . ?
O1 N1 C1 C5 -170.5(3) . . . . ?
O2 N1 C1 C2 -173.4(3) . . . . ?
O2 N1 C1 C5 9.2(4) . . . . ?
N1 C1 C2 C3 -178.2(3) . . . . ?
N1 C1 C5 N2 177.5(2) . . . . ?
N2 C6 C7 C8 159.6(4) . . . . ?
N2 C6 C9 O4A -65.4(7) . . . . ?
N2 C6 C10 O4 54.8(4) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
C2 C1 C5 N2 0.1(5) . . . . ?
C2 C3 C4 O3 -176.6(3) . . . . ?
C2 C3 C4 N2 3.0(5) . . . . ?
C4 N2 C5 C1 2.4(4) . . . . ?
C4 N2 C6 C7 -54.7(4) . . . . ?
C4 N2 C6 C9 -172.7(3) . . . . ?
C4 N2 C6 C10 67.0(4) . . . . ?
C5 N2 C4 O3 175.8(3) . . . . ?
C5 N2 C4 C3 -3.8(4) . . . . ?
C5 N2 C6 C7 127.2(3) . . . . ?
C5 N2 C6 C9 9.3(4) . . . . ?
C5 N2 C6 C10 -111.1(3) . . . . ?
C5 C1 C2 C3 -0.9(5) . . . . ?
C6 N2 C4 O3 -2.2(5) . . . . ?
C6 N2 C4 C3 178.2(2) . . . . ?
C6 N2 C5 C1 -179.6(3) . . . . ?
C7 C6 C9 O4A 176.7(7) . . . . ?
C7 C6 C10 O4 173.9(3) . . . . ?
C9 C6 C7 C8 -81.1(5) . . . . ?
C9 C6 C10 O4 -65.7(3) . . . . ?
C10 C6 C7 C8 40.4(6) . . . . ?
C10 C6 C9 O4A 53.8(7) . . . . ?
O5 N3 C11 C12 -9.9(4) . . . . ?
O5 N3 C11 C15 167.9(3) . . . . ?
O6 N3 C11 C12 171.0(3) . . . . ?
O6 N3 C11 C15 -11.2(4) . . . . ?
N3 C11 C12 C13 177.7(3) . . . . ?
N3 C11 C15 N4 -177.6(2) . . . . ?
N4 C16 C17 C18 -155.4(4) . . . . ?
N4 C16 C20 O8 67.7(3) . . . . ?
C11 C12 C13 C14 0.9(5) . . . . ?
C12 C11 C15 N4 0.2(5) . . . . ?
C12 C13 C14 O7 179.0(3) . . . . ?
C12 C13 C14 N4 -1.9(5) . . . . ?
C14 N4 C15 C11 -1.3(5) . . . . ?
C14 N4 C16 C17 56.5(4) . . . . ?
C14 N4 C16 C19 -68.6(4) . . . . ?
C14 N4 C16 C20 170.7(3) . . . . ?
C15 N4 C14 O7 -178.8(3) . . . . ?
C15 N4 C14 C13 2.0(5) . . . . ?
C15 N4 C16 C17 -123.2(3) . . . . ?
C15 N4 C16 C19 111.7(3) . . . . ?
C15 N4 C16 C20 -9.1(4) . . . . ?
C15 C11 C12 C13 0.0(5) . . . . ?
C16 N4 C14 O7 1.5(5) . . . . ?
C16 N4 C14 C13 -177.7(2) . . . . ?
C16 N4 C15 C11 178.5(2) . . . . ?
C17 C16 C20 O8 -176.9(2) . . . . ?
C19 C16 C17 C18 -34.2(5) . . . . ?
C19 C16 C20 O8 -52.4(3) . . . . ?
C20 C16 C17 C18 86.9(4) . . . . ?
