#------------------------------------------------------------------------------
#$Date: 2025-08-21 04:34:05 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301843 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/74/4517481.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_4517481
loop_
_publ_author_name
'Tan, Jin-Fay'
'Bormann, Carl Thomas'
'Severin, Kay'
'Cramer, Nicolai'
_publ_section_title
;
 Alkynyl Triazenes as Fluoroalkyne Surrogates: Regioselective Access to
 4-Fluoro-2-pyridones by a Rh(III)-Catalyzed C--H Activation--Lossen
 Rearrangement--Wallach Reaction
;
_journal_issue                   6
_journal_name_full               'ACS Catalysis'
_journal_page_first              3790
_journal_page_last               3796
_journal_paper_doi               10.1021/acscatal.0c00499
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C21 H24 N4 O'
_chemical_formula_sum            'C21 H24 N4 O'
_chemical_formula_weight         348.44
_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   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-02-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                97.909(11)
_cell_angle_beta                 105.084(11)
_cell_angle_gamma                114.113(11)
_cell_formula_units_Z            2
_cell_length_a                   9.6626(11)
_cell_length_b                   10.1376(12)
_cell_length_c                   11.1294(15)
_cell_measurement_reflns_used    2030
_cell_measurement_temperature    100.01(12)
_cell_measurement_theta_max      28.7610
_cell_measurement_theta_min      3.6570
_cell_volume                     923.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.20a (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(12)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.838
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -57.00  37.00   1.00    8.16    --   11.81 -57.00  60.00   94
  2  ω    -18.00  78.00   1.00    8.16    --   11.81  77.00 -30.00   96
  3  ω    -16.00  85.00   1.00    8.16    --   11.81  57.00-150.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0813926000
_diffrn_orient_matrix_UB_12      0.0500200000
_diffrn_orient_matrix_UB_13      0.0398600000
_diffrn_orient_matrix_UB_21      0.0270821000
_diffrn_orient_matrix_UB_22      -0.0252465000
_diffrn_orient_matrix_UB_23      -0.0475132000
_diffrn_orient_matrix_UB_31      -0.0036157000
_diffrn_orient_matrix_UB_32      0.0567826000
_diffrn_orient_matrix_UB_33      -0.0295292000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.838
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6709
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.392
_diffrn_reflns_theta_min         3.011
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.296
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.20a (Rigaku Oxford Diffraction, 2018).
 Numerical absorption correction based on Gaussian integration over
 a multifaceted crystal model/Empirical absorption correction using
 spherical harmonics as implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       prism
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.479
_exptl_crystal_size_mid          0.334
_exptl_crystal_size_min          0.247
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         4264
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0683
_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)+(0.0751P)²+0.7871P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1658
_refine_ls_wR_factor_ref         0.1834
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3044
_reflns_number_total             4264
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs0c00499_si_003.cif
_cod_data_source_block           jft-01-354
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Gaussian' was
changed to 'gaussian' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/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 4517481--4517482.cif.

 Adding full bibliography for 4517481--4517482.cif.
;
_cod_database_code               4517481
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C21 H24 N4 O'
_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.
;
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
;
_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.455
_oxdiff_exptl_absorpt_empirical_full_min 0.729
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
O1 O 0.8603(2) 1.03725(19) 0.40035(18) 0.0268(4) Uani 1 1 d . . . . .
N1 N 0.4413(2) 0.6486(2) 0.59546(19) 0.0197(4) Uani 1 1 d . . . . .
N2 N 0.4788(2) 0.6982(2) 0.71665(19) 0.0197(4) Uani 1 1 d . . . . .
N3 N 0.3971(2) 0.6010(2) 0.77196(19) 0.0209(4) Uani 1 1 d . . . . .
N4 N 0.8135(3) 0.8968(2) 0.5413(2) 0.0209(4) Uani 1 1 d . . . . .
H4 H 0.917(4) 0.924(3) 0.567(3) 0.037(9) Uiso 1 1 d . . . . .
C1 C 0.5517(3) 0.7515(2) 0.5484(2) 0.0190(5) Uani 1 1 d . . . . .
C2 C 0.7151(3) 0.8000(2) 0.5960(2) 0.0191(5) Uani 1 1 d . . . . .
C3 C 0.7628(3) 0.9525(2) 0.4441(2) 0.0211(5) Uani 1 1 d . . . . .
C4 C 0.5885(3) 0.9039(2) 0.3945(2) 0.0197(5) Uani 1 1 d . . . . .
C5 C 0.5273(3) 0.9630(3) 0.3000(2) 0.0222(5) Uani 1 1 d . . . . .
H5 H 0.595(3) 1.031(3) 0.266(2) 0.020(6) Uiso 1 1 d . . . . .
C6 C 0.3641(3) 0.9222(3) 0.2562(2) 0.0232(5) Uani 1 1 d . . . . .
H6 H 0.322(3) 0.966(3) 0.188(3) 0.029(7) Uiso 1 1 d . . . . .
C7 C 0.2599(3) 0.8205(3) 0.3051(2) 0.0231(5) Uani 1 1 d . . . . .
H7 H 0.135(4) 0.791(3) 0.271(3) 0.030(7) Uiso 1 1 d . . . . .
C8 C 0.3188(3) 0.7618(3) 0.3978(2) 0.0215(5) Uani 1 1 d . . . . .
H8 H 0.254(3) 0.697(3) 0.437(2) 0.021(7) Uiso 1 1 d . . . . .
C9 C 0.4853(3) 0.8030(2) 0.4453(2) 0.0194(5) Uani 1 1 d . . . . .
C10 C 0.7989(3) 0.7618(3) 0.7065(2) 0.0206(5) Uani 1 1 d . . . . .
C11 C 0.7404(3) 0.6143(3) 0.7166(3) 0.0244(5) Uani 1 1 d . . . . .
H11 H 0.649(3) 0.530(3) 0.641(3) 0.022(7) Uiso 1 1 d . . . . .
C12 C 0.8114(3) 0.5824(3) 0.8255(3) 0.0266(6) Uani 1 1 d . . . . .
H12 H 0.769(3) 0.479(3) 0.832(2) 0.027(7) Uiso 1 1 d . . . . .
C13 C 0.9450(3) 0.6970(3) 0.9261(3) 0.0284(6) Uani 1 1 d . . . . .
H13 H 0.996(3) 0.678(3) 1.004(3) 0.024(7) Uiso 1 1 d . . . . .
C14 C 1.0071(3) 0.8429(3) 0.9149(3) 0.0299(6) Uani 1 1 d . . . . .
H14 H 1.102(4) 0.930(3) 0.989(3) 0.038(8) Uiso 1 1 d . . . . .
C15 C 0.9358(3) 0.8749(3) 0.8063(3) 0.0254(5) Uani 1 1 d . . . . .
H15 H 0.977(4) 0.979(3) 0.795(3) 0.034(8) Uiso 1 1 d . . . . .
C16 C 0.4258(3) 0.6615(3) 0.9086(2) 0.0242(5) Uani 1 1 d . . . . .
H16 H 0.431(3) 0.586(3) 0.951(2) 0.021(7) Uiso 1 1 d . . . . .
C17 C 0.5844(4) 0.8069(3) 0.9726(3) 0.0285(6) Uani 1 1 d . . . . .
H17A H 0.607(3) 0.835(3) 1.066(3) 0.022(7) Uiso 1 1 d . . . . .
H17B H 0.582(4) 0.887(3) 0.935(3) 0.039(8) Uiso 1 1 d . . . . .
H17C H 0.671(4) 0.796(4) 0.956(3) 0.046(9) Uiso 1 1 d . . . . .
C18 C 0.2847(4) 0.6851(4) 0.9253(3) 0.0373(7) Uani 1 1 d . . . . .
H18A H 0.310(4) 0.726(3) 1.018(3) 0.031(8) Uiso 1 1 d . . . . .
H18B H 0.268(4) 0.750(4) 0.875(3) 0.043(9) Uiso 1 1 d . . . . .
H18C H 0.181(4) 0.593(4) 0.892(3) 0.043(9) Uiso 1 1 d . . . . .
C19 C 0.2746(3) 0.4462(3) 0.6945(2) 0.0232(5) Uani 1 1 d . . . . .
H19 H 0.314(4) 0.416(3) 0.630(3) 0.029(7) Uiso 1 1 d . . . . .
C20 C 0.2509(4) 0.3373(3) 0.7773(3) 0.0300(6) Uani 1 1 d . . . . .
H20A H 0.352(4) 0.336(3) 0.823(3) 0.039(9) Uiso 1 1 d . . . . .
H20B H 0.183(4) 0.233(4) 0.723(3) 0.039(8) Uiso 1 1 d . . . . .
H20C H 0.214(4) 0.362(3) 0.845(3) 0.038(8) Uiso 1 1 d . . . . .
C21 C 0.1155(3) 0.4386(3) 0.6160(3) 0.0328(6) Uani 1 1 d . . . . .
H21A H 0.141(4) 0.506(4) 0.566(3) 0.039(8) Uiso 1 1 d . . . . .
H21B H 0.043(4) 0.336(4) 0.551(3) 0.043(9) Uiso 1 1 d . . . . .
H21C H 0.060(4) 0.465(3) 0.678(3) 0.043(9) 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.1272
0 1 0 0.2113
0 -1 0 0.1966
0 -2 -1 0.1852
-1 2 -2 0.1591
-1 -2 -1 0.1933
-1 0 -2 0.1406
0 -2 1 0.2065
-2 -2 -1 0.1910
-2 1 -2 0.1737
0 2 -1 0.2053
-2 2 -1 0.1915
2 -2 1 0.1625
-1 -1 1 0.2007
-2 -1 2 0.1798
2 1 -2 0.3012
1 -1 0 0.1731
-1 1 0 0.1884
-1 0 1 0.1647
-1 -1 2 0.1706
-2 1 2 0.1477
2 -1 -2 0.2468
2 -2 -1 0.1659
-2 2 1 0.1692
-1 0 2 0.1221
-1 1 1 0.1494
-1 2 0 0.1575
1 -2 0 0.1770
0 1 -2 0.1867
-1 2 1 0.1490
1 -2 -1 0.1842
5 0 11 0.1067
6 -6 12 0.1209
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
N2 N1 C1 111.09(18) . . ?
N1 N2 N3 115.19(19) . . ?
N2 N3 C16 115.76(18) . . ?
N2 N3 C19 120.55(19) . . ?
C16 N3 C19 123.46(18) . . ?
C2 N4 H4 120(2) . . ?
C3 N4 H4 114(2) . . ?
C3 N4 C2 125.8(2) . . ?
N1 C1 C9 117.4(2) . . ?
C2 C1 N1 123.0(2) . . ?
C2 C1 C9 119.6(2) . . ?
N4 C2 C10 116.1(2) . . ?
C1 C2 N4 119.1(2) . . ?
C1 C2 C10 124.7(2) . . ?
O1 C3 N4 121.0(2) . . ?
O1 C3 C4 123.4(2) . . ?
N4 C3 C4 115.5(2) . . ?
C5 C4 C3 119.3(2) . . ?
C5 C4 C9 120.6(2) . . ?
C9 C4 C3 120.0(2) . . ?
C4 C5 H5 121.1(17) . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 H5 119.1(16) . . ?
C5 C6 H6 118.9(17) . . ?
C5 C6 C7 120.1(2) . . ?
C7 C6 H6 121.0(17) . . ?
C6 C7 H7 119.1(15) . . ?
C8 C7 C6 120.6(2) . . ?
C8 C7 H7 120.3(15) . . ?
C7 C8 H8 123.6(17) . . ?
C7 C8 C9 120.4(2) . . ?
C9 C8 H8 115.9(17) . . ?
C4 C9 C1 119.9(2) . . ?
C4 C9 C8 118.5(2) . . ?
C8 C9 C1 121.5(2) . . ?
C11 C10 C2 121.5(2) . . ?
C15 C10 C2 120.0(2) . . ?
C15 C10 C11 118.5(2) . . ?
C10 C11 H11 119.0(15) . . ?
C12 C11 C10 120.9(2) . . ?
C12 C11 H11 120.0(15) . . ?
C11 C12 H12 119.9(16) . . ?
C11 C12 C13 120.1(2) . . ?
C13 C12 H12 120.0(16) . . ?
C12 C13 H13 121.6(16) . . ?
C14 C13 C12 119.4(3) . . ?
C14 C13 H13 119.0(16) . . ?
C13 C14 H14 121.3(17) . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 118.0(17) . . ?
C10 C15 H15 116.8(17) . . ?
C14 C15 C10 120.6(2) . . ?
C14 C15 H15 122.6(17) . . ?
N3 C16 H16 106.2(15) . . ?
N3 C16 C17 111.9(2) . . ?
N3 C16 C18 111.6(2) . . ?
C17 C16 H16 109.2(16) . . ?
C17 C16 C18 110.5(2) . . ?
C18 C16 H16 107.2(16) . . ?
C16 C17 H17A 108.9(15) . . ?
C16 C17 H17B 111.7(19) . . ?
C16 C17 H17C 111(2) . . ?
H17A C17 H17B 111(2) . . ?
H17A C17 H17C 111(3) . . ?
H17B C17 H17C 103(3) . . ?
C16 C18 H18A 108.6(18) . . ?
C16 C18 H18B 109(2) . . ?
C16 C18 H18C 114(2) . . ?
H18A C18 H18B 113(3) . . ?
H18A C18 H18C 109(3) . . ?
H18B C18 H18C 105(3) . . ?
N3 C19 H19 106.9(17) . . ?
N3 C19 C20 111.7(2) . . ?
N3 C19 C21 112.4(2) . . ?
C20 C19 H19 108.9(17) . . ?
C20 C19 C21 112.2(2) . . ?
C21 C19 H19 104.2(17) . . ?
C19 C20 H20A 112.3(18) . . ?
C19 C20 H20B 110.6(18) . . ?
C19 C20 H20C 113.1(19) . . ?
H20A C20 H20B 102(3) . . ?
H20A C20 H20C 105(3) . . ?
H20B C20 H20C 114(3) . . ?
C19 C21 H21A 106(2) . . ?
C19 C21 H21B 110.0(19) . . ?
C19 C21 H21C 110.1(18) . . ?
H21A C21 H21B 105(2) . . ?
H21A C21 H21C 113(3) . . ?
H21B C21 H21C 112(3) . . ?
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 C3 1.247(3) . ?
N1 N2 1.270(3) . ?
N1 C1 1.425(3) . ?
N2 N3 1.326(3) . ?
N3 C16 1.467(3) . ?
N3 C19 1.478(3) . ?
N4 H4 0.87(4) . ?
N4 C2 1.393(3) . ?
N4 C3 1.360(3) . ?
C1 C2 1.369(3) . ?
C1 C9 1.435(3) . ?
C2 C10 1.479(3) . ?
C3 C4 1.466(3) . ?
C4 C5 1.398(3) . ?
C4 C9 1.406(3) . ?
C5 H5 0.94(3) . ?
C5 C6 1.381(4) . ?
C6 H6 1.01(3) . ?
C6 C7 1.402(3) . ?
C7 H7 1.06(3) . ?
C7 C8 1.372(4) . ?
C8 H8 0.95(3) . ?
C8 C9 1.411(3) . ?
C10 C11 1.399(3) . ?
C10 C15 1.394(4) . ?
C11 H11 1.01(3) . ?
C11 C12 1.378(4) . ?
C12 H12 0.98(3) . ?
C12 C13 1.390(4) . ?
C13 H13 0.97(3) . ?
C13 C14 1.389(4) . ?
C14 H14 1.02(3) . ?
C14 C15 1.377(4) . ?
C15 H15 1.00(3) . ?
C16 H16 0.97(3) . ?
C16 C17 1.525(4) . ?
C16 C18 1.529(4) . ?
C17 H17A 0.98(3) . ?
C17 H17B 0.97(3) . ?
C17 H17C 0.95(4) . ?
C18 H18A 0.98(3) . ?
C18 H18B 0.95(3) . ?
C18 H18C 0.98(3) . ?
C19 H19 0.97(3) . ?
C19 C20 1.518(3) . ?
C19 C21 1.523(4) . ?
C20 H20A 0.98(4) . ?
C20 H20B 0.98(3) . ?
C20 H20C 0.96(3) . ?
C21 H21A 0.93(3) . ?
C21 H21B 1.02(3) . ?
C21 H21C 1.04(3) . ?
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
_geom_hbond_publ_flag
N4 H4 O1 0.87(4) 1.95(4) 2.809(3) 171(3) 2_776 yes
C21 H21A N1 0.93(3) 2.56(3) 3.087(3) 116(2) . yes
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 C3 C4 C5 -5.0(4) . . . . ?
O1 C3 C4 C9 177.3(2) . . . . ?
N1 N2 N3 C16 -173.4(2) . . . . ?
N1 N2 N3 C19 1.2(3) . . . . ?
N1 C1 C2 N4 177.9(2) . . . . ?
N1 C1 C2 C10 -4.5(4) . . . . ?
N1 C1 C9 C4 -179.6(2) . . . . ?
N1 C1 C9 C8 4.1(3) . . . . ?
N2 N1 C1 C2 56.9(3) . . . . ?
N2 N1 C1 C9 -124.1(2) . . . . ?
N2 N3 C16 C17 -20.0(3) . . . . ?
N2 N3 C16 C18 104.4(2) . . . . ?
N2 N3 C19 C20 154.6(2) . . . . ?
N2 N3 C19 C21 -78.2(3) . . . . ?
N4 C2 C10 C11 -136.1(2) . . . . ?
N4 C2 C10 C15 46.5(3) . . . . ?
N4 C3 C4 C5 176.1(2) . . . . ?
N4 C3 C4 C9 -1.5(3) . . . . ?
C1 N1 N2 N3 -170.79(19) . . . . ?
C1 C2 C10 C11 46.2(3) . . . . ?
C1 C2 C10 C15 -131.2(3) . . . . ?
C2 N4 C3 O1 -179.1(2) . . . . ?
C2 N4 C3 C4 -0.2(3) . . . . ?
C2 C1 C9 C4 -0.5(3) . . . . ?
C2 C1 C9 C8 -176.8(2) . . . . ?
C2 C10 C11 C12 -174.3(2) . . . . ?
C2 C10 C15 C14 174.5(2) . . . . ?
C3 N4 C2 C1 1.6(3) . . . . ?
C3 N4 C2 C10 -176.2(2) . . . . ?
C3 C4 C5 C6 -177.6(2) . . . . ?
C3 C4 C9 C1 1.9(3) . . . . ?
C3 C4 C9 C8 178.3(2) . . . . ?
C4 C5 C6 C7 -0.8(4) . . . . ?
C5 C4 C9 C1 -175.7(2) . . . . ?
C5 C4 C9 C8 0.7(3) . . . . ?
C5 C6 C7 C8 0.7(4) . . . . ?
C6 C7 C8 C9 0.0(4) . . . . ?
C7 C8 C9 C1 175.6(2) . . . . ?
C7 C8 C9 C4 -0.7(3) . . . . ?
C9 C1 C2 N4 -1.2(3) . . . . ?
C9 C1 C2 C10 176.4(2) . . . . ?
C9 C4 C5 C6 0.1(3) . . . . ?
C10 C11 C12 C13 -1.3(4) . . . . ?
C11 C10 C15 C14 -3.0(4) . . . . ?
C11 C12 C13 C14 -0.8(4) . . . . ?
C12 C13 C14 C15 1.1(4) . . . . ?
C13 C14 C15 C10 0.9(4) . . . . ?
C15 C10 C11 C12 3.2(4) . . . . ?
C16 N3 C19 C20 -31.2(3) . . . . ?
C16 N3 C19 C21 95.9(3) . . . . ?
C19 N3 C16 C17 165.5(2) . . . . ?
C19 N3 C16 C18 -70.1(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168346582
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 0.0000 -1.0000 -0.0399 0.0475 0.0295
-0.0000 1.0000 0.0000 0.0500 -0.0252 0.0568
0.0000 -1.0000 -0.0000 -0.0500 0.0252 -0.0568
0.0000 -2.0000 -1.0000 -0.1399 0.0980 -0.0840
-1.0000 2.0000 -2.0000 -0.0611 0.0175 0.1762
-1.0000 -2.0000 -1.0000 -0.2213 0.0709 -0.0804
-1.0000 0.0000 -2.0000 -0.1611 0.0679 0.0627
0.0000 -2.0000 1.0000 -0.0602 0.0030 -0.1431
-2.0000 -2.0000 -1.0000 -0.3027 0.0438 -0.0768
-2.0000 1.0000 -2.0000 -0.1925 0.0156 0.1231
-0.0000 2.0000 -1.0000 0.0602 -0.0030 0.1431
-2.0000 2.0000 -1.0000 -0.1026 -0.0571 0.1503
2.0000 -2.0000 1.0000 0.1026 0.0571 -0.1503
-1.0000 -1.0000 1.0000 -0.0916 -0.0493 -0.0827
-2.0000 -1.0000 2.0000 -0.1331 -0.1239 -0.1086
2.0000 1.0000 -2.0000 0.1331 0.1239 0.1086
1.0000 -1.0000 0.0000 0.0314 0.0523 -0.0604
-1.0000 1.0000 -0.0000 -0.0314 -0.0523 0.0604
-1.0000 -0.0000 1.0000 -0.0415 -0.0746 -0.0259
-1.0000 -1.0000 2.0000 -0.0517 -0.0969 -0.1122
-2.0000 1.0000 2.0000 -0.0330 -0.1744 0.0050
2.0000 -1.0000 -2.0000 0.0330 0.1744 -0.0050
2.0000 -2.0000 -1.0000 0.0229 0.1522 -0.0913
-2.0000 2.0000 1.0000 -0.0229 -0.1522 0.0913
-1.0000 -0.0000 2.0000 -0.0017 -0.1221 -0.0554
-1.0000 1.0000 1.0000 0.0085 -0.0998 0.0309
-1.0000 2.0000 0.0000 0.0186 -0.0776 0.1172
1.0000 -2.0000 -0.0000 -0.0186 0.0776 -0.1172
-0.0000 1.0000 -2.0000 -0.0297 0.0698 0.1158
-1.0000 2.0000 1.0000 0.0585 -0.1251 0.0877
1.0000 -2.0000 -1.0000 -0.0585 0.1251 -0.0877
5.0000 -0.0000 11.0000 0.8454 -0.3872 -0.3429
6.0000 -6.0000 12.0000 0.6666 -0.2562 -0.7167
