#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:34:05 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301843 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/85/4518573.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_4518573
loop_
_publ_author_name
'Gou, Xue-Ya'
'Li, Yuke'
'Luan, Yu-Yong'
'Shi, Wei-Yu'
'Wang, Cui-Tian'
'An, Yang'
'Zhang, Bo-Sheng'
'Liang, Yong-Min'
_publ_section_title
;
 Ruthenium-Catalyzed Radical Cyclization/meta-Selective C--H Alkylation of
 Arenes via σ-Activation Strategy
;
_journal_issue                   7
_journal_name_full               'ACS Catalysis'
_journal_page_first              4263
_journal_page_last               4270
_journal_paper_doi               10.1021/acscatal.1c00359
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C25 H28 N2 O4'
_chemical_formula_sum            'C25 H28 N2 O4'
_chemical_formula_weight         420.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-12-28
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.726(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4070(5)
_cell_length_b                   11.0997(12)
_cell_length_c                   31.594(4)
_cell_measurement_reflns_used    2978
_cell_measurement_temperature    287(1)
_cell_measurement_theta_max      66.4220
_cell_measurement_theta_min      2.8040
_cell_volume                     2245.8(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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      air
_diffrn_ambient_temperature      287(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -34.00  26.00   1.00    1.00    --   43.05 -19.00   0.00   60
  2  ω    -37.00  23.00   1.00    1.00    --   43.05 -19.00 -60.00   60
  3  ω     66.00  96.00   1.00    3.50    --  109.26 -94.00 -60.00   30
  4  ω     38.00 108.00   1.00    3.50    --  109.26 -77.00 -30.00   70
  5  ω     54.00  84.00   1.00    1.00    --   43.05-138.00 127.00   30
  6  ω     36.00  86.00   1.00    3.50    --  109.26-138.00 127.00   50
  7  ω     81.00 121.00   1.00    3.50    --  109.26-138.00 127.00   40
  8  ω     66.00  96.00   1.00    3.50    --  109.26 -94.00 150.00   30
  9  ω     21.00  91.00   1.00    1.00    --   43.05-131.00 -57.00   70
 10  ω    -19.00  31.00   1.00    1.00    --  -43.05  19.00 -90.00   50
 11  ω    -53.00 -33.00   1.00    3.50    -- -100.00  45.00-180.00   20
 12  ω    -54.00 -24.00   1.00    3.50    -- -100.00  45.00-120.00   30
 13  ω    -54.00 -24.00   1.00    3.50    -- -100.00  45.00 -60.00   30
 14  ω    -70.00 -30.00   1.00    3.50    -- -100.00  61.00-120.00   40
 15  ω    -54.00 -24.00   1.00    3.50    -- -100.00  45.00-150.00   30
 16  ω    -91.00 -61.00   1.00    1.00    --  -43.05 138.00-170.00   30
 17  ω   -117.00 -37.00   1.00    3.50    -- -100.00 138.00-170.00   80
 18  ω     68.00 108.00   1.00    1.00    --   43.05 138.00-170.00   40
 19  ω     92.00 122.00   1.00    3.50    --  109.26  45.00 120.00   30
 20  ω    126.00 166.00   1.00    3.50    --  109.26  45.00 120.00   40
 21  ω     99.00 129.00   1.00    3.50    --  109.26 131.00  13.00   30
 22  ω    -54.00 -24.00   1.00    3.50    -- -100.00  45.00 120.00   30
 23  ω    -54.00 -24.00   1.00    3.50    -- -100.00  45.00 150.00   30
 24  ω   -148.00-118.00   1.00    3.50    -- -100.00-138.00 127.00   30
 25  ω   -112.00 -82.00   1.00    3.50    -- -100.00-125.00  90.00   30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0089937000
_diffrn_orient_matrix_UB_12      -0.1295650000
_diffrn_orient_matrix_UB_13      -0.0172585000
_diffrn_orient_matrix_UB_21      0.0019284000
_diffrn_orient_matrix_UB_22      0.0493603000
_diffrn_orient_matrix_UB_23      -0.0455491000
_diffrn_orient_matrix_UB_31      0.2405578000
_diffrn_orient_matrix_UB_32      0.0046423000
_diffrn_orient_matrix_UB_33      0.0024596000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            12770
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.836
_diffrn_reflns_theta_min         2.799
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (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    1.244
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0013(3)
_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   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4286
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.1099
_refine_ls_R_factor_gt           0.0693
_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)+(0.0854P)²+0.4506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1752
_refine_ls_wR_factor_ref         0.2085
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2683
_reflns_number_total             4286
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c00359_si_004.cif
_cod_data_source_block           gouxy_1225_2_2
_cod_depositor_comments
'Adding full bibliography for 4518571--4518573.cif.'
_cod_database_code               4518573
_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   0.993
_shelx_estimated_absorpt_t_min   0.973
_reflns_odcompleteness_completeness 97.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C21(H21A,H21B), C22(H22A,H22B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C15(H15), C17(H17), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C25(H25A,H25B,H25C)
;
_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 2.892
_oxdiff_exptl_absorpt_empirical_full_min 0.610
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.6417(5) 1.0352(2) 0.61835(11) 0.1182(10) Uani 1 1 d . . . . .
O2 O 0.2073(3) 0.6416(2) 0.50473(7) 0.0835(7) Uani 1 1 d . . . . .
O3 O 0.0144(3) 0.6869(3) 0.55984(7) 0.0928(8) Uani 1 1 d . . . . .
O4 O -0.0308(4) 0.2618(2) 0.68677(9) 0.0964(8) Uani 1 1 d . . . . .
N1 N 0.6978(3) 0.8404(2) 0.64090(8) 0.0656(6) Uani 1 1 d . . . . .
N2 N -0.1257(4) 0.4545(3) 0.68184(10) 0.0839(8) Uani 1 1 d . . . . .
C1 C 0.8738(4) 0.8550(3) 0.66863(9) 0.0668(8) Uani 1 1 d . . . . .
C2 C 0.9634(6) 0.9663(4) 0.67690(12) 0.0878(10) Uani 1 1 d . . . . .
H2 H 0.903012 1.035343 0.665211 0.105 Uiso 1 1 calc R . . . .
C3 C 1.1399(7) 0.9756(4) 0.70211(13) 0.1053(13) Uani 1 1 d . . . . .
H3 H 1.200532 1.050831 0.706668 0.126 Uiso 1 1 calc R . . . .
C4 C 1.2283(7) 0.8763(5) 0.72065(14) 0.1072(13) Uani 1 1 d . . . . .
H4 H 1.347547 0.883692 0.737977 0.129 Uiso 1 1 calc R . . . .
C5 C 1.1403(5) 0.7661(4) 0.71357(11) 0.0897(11) Uani 1 1 d . . . . .
H5 H 1.199580 0.698260 0.726326 0.108 Uiso 1 1 calc R . . . .
C6 C 0.9637(4) 0.7540(3) 0.68762(10) 0.0718(8) Uani 1 1 d . . . . .
H6 H 0.905251 0.678278 0.682901 0.086 Uiso 1 1 calc R . . . .
C7 C 0.6156(4) 0.7218(3) 0.63041(10) 0.0626(7) Uani 1 1 d . . . . .
H7A H 0.578833 0.678731 0.655831 0.075 Uiso 1 1 calc R . . . .
H7B H 0.717525 0.674851 0.615439 0.075 Uiso 1 1 calc R . . . .
C8 C 0.4221(4) 0.7451(3) 0.60222(9) 0.0630(7) Uani 1 1 d . . . . .
H8 H 0.302776 0.753137 0.620704 0.076 Uiso 1 1 calc R . . . .
C9 C 0.4633(4) 0.8700(3) 0.58272(10) 0.0667(8) Uani 1 1 d . . . . .
C10 C 0.6069(5) 0.9286(3) 0.61579(11) 0.0780(9) Uani 1 1 d . . . . .
C11 C 0.5856(5) 0.8652(3) 0.54193(11) 0.0844(10) Uani 1 1 d . . . . .
H11A H 0.705974 0.814596 0.546156 0.127 Uiso 1 1 calc GR . . . .
H11B H 0.629435 0.944948 0.534547 0.127 Uiso 1 1 calc GR . . . .
H11C H 0.498109 0.832888 0.519479 0.127 Uiso 1 1 calc GR . . . .
C12 C 0.2671(5) 0.9472(3) 0.57573(14) 0.0945(11) Uani 1 1 d . . . . .
H12A H 0.183054 0.914043 0.552921 0.142 Uiso 1 1 calc GR . . . .
H12B H 0.306910 1.028030 0.568781 0.142 Uiso 1 1 calc GR . . . .
H12C H 0.188453 0.947891 0.601116 0.142 Uiso 1 1 calc GR . . . .
C13 C 0.3758(4) 0.6404(3) 0.57188(9) 0.0634(7) Uani 1 1 d . . . . .
H13 H 0.492558 0.633635 0.552674 0.076 Uiso 1 1 calc R . . . .
C14 C 0.3543(4) 0.5200(3) 0.59483(9) 0.0602(7) Uani 1 1 d . . . . .
C15 C 0.1978(4) 0.5008(3) 0.62313(9) 0.0589(7) Uani 1 1 d . . . . .
H15 H 0.107655 0.563582 0.629397 0.071 Uiso 1 1 calc R . . . .
C16 C 0.1719(4) 0.3892(3) 0.64251(9) 0.0622(7) Uani 1 1 d . . . . .
C17 C 0.3101(5) 0.2975(3) 0.63408(12) 0.0816(9) Uani 1 1 d . . . . .
H17 H 0.295823 0.222845 0.647055 0.098 Uiso 1 1 calc R . . . .
C18 C 0.4682(6) 0.3162(4) 0.60663(14) 0.0961(12) Uani 1 1 d . . . . .
H18 H 0.561422 0.254306 0.601189 0.115 Uiso 1 1 calc R . . . .
C19 C 0.4905(5) 0.4265(3) 0.58695(12) 0.0847(10) Uani 1 1 d . . . . .
H19 H 0.597986 0.437850 0.568228 0.102 Uiso 1 1 calc R . . . .
C20 C -0.0018(5) 0.3722(3) 0.67126(10) 0.0685(8) Uani 1 1 d . . . . .
C21 C -0.2743(6) 0.3998(4) 0.71051(14) 0.0997(12) Uani 1 1 d . . . . .
H21A H -0.416449 0.409592 0.699636 0.120 Uiso 1 1 calc R . . . .
H21B H -0.262293 0.436027 0.738428 0.120 Uiso 1 1 calc R . . . .
C22 C -0.2143(6) 0.2684(4) 0.71219(15) 0.1049(13) Uani 1 1 d . . . . .
H22A H -0.182815 0.243097 0.741066 0.126 Uiso 1 1 calc R . . . .
H22B H -0.325595 0.218230 0.700386 0.126 Uiso 1 1 calc R . . . .
C23 C 0.1789(4) 0.6605(3) 0.54538(10) 0.0685(8) Uani 1 1 d . . . . .
C24 C 0.0274(5) 0.6617(4) 0.47608(12) 0.0948(12) Uani 1 1 d . . . . .
H24A H -0.100321 0.644992 0.490744 0.114 Uiso 1 1 calc R . . . .
H24B H 0.034010 0.607274 0.452124 0.114 Uiso 1 1 calc R . . . .
C25 C 0.0253(7) 0.7870(5) 0.46099(15) 0.1193(15) Uani 1 1 d . . . . .
H25A H -0.086279 0.797403 0.440362 0.179 Uiso 1 1 calc GR . . . .
H25B H 0.156048 0.805025 0.448335 0.179 Uiso 1 1 calc GR . . . .
H25C H 0.004936 0.840293 0.484430 0.179 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
C23 O2 C24 116.7(2) . . ?
C20 O4 C22 106.4(3) . . ?
C1 N1 C7 121.5(2) . . ?
C10 N1 C1 126.1(3) . . ?
C10 N1 C7 111.6(2) . . ?
C20 N2 C21 106.8(3) . . ?
C2 C1 N1 122.5(3) . . ?
C2 C1 C6 118.4(3) . . ?
C6 C1 N1 119.1(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(4) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.0(4) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.8(4) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.9(3) . . ?
C5 C6 H6 120.1 . . ?
N1 C7 H7A 110.7 . . ?
N1 C7 H7B 110.7 . . ?
N1 C7 C8 105.2(2) . . ?
H7A C7 H7B 108.8 . . ?
C8 C7 H7A 110.7 . . ?
C8 C7 H7B 110.7 . . ?
C7 C8 H8 107.6 . . ?
C7 C8 C9 103.9(2) . . ?
C7 C8 C13 112.1(2) . . ?
C9 C8 H8 107.6 . . ?
C13 C8 H8 107.6 . . ?
C13 C8 C9 117.7(2) . . ?
C10 C9 C8 102.5(2) . . ?
C10 C9 C11 106.3(3) . . ?
C10 C9 C12 109.7(3) . . ?
C11 C9 C8 113.8(3) . . ?
C11 C9 C12 109.7(3) . . ?
C12 C9 C8 114.2(2) . . ?
O1 C10 N1 125.7(3) . . ?
O1 C10 C9 125.0(3) . . ?
N1 C10 C9 109.2(3) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13 108.0 . . ?
C14 C13 C8 112.7(2) . . ?
C14 C13 H13 108.0 . . ?
C23 C13 C8 112.2(2) . . ?
C23 C13 H13 108.0 . . ?
C23 C13 C14 107.9(2) . . ?
C15 C14 C13 121.4(2) . . ?
C15 C14 C19 118.3(3) . . ?
C19 C14 C13 120.3(3) . . ?
C14 C15 H15 119.3 . . ?
C14 C15 C16 121.4(3) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C20 119.2(3) . . ?
C17 C16 C15 119.0(3) . . ?
C17 C16 C20 121.7(3) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.1(3) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.5(3) . . ?
C19 C18 H18 119.7 . . ?
C14 C19 H19 119.7 . . ?
C18 C19 C14 120.6(3) . . ?
C18 C19 H19 119.7 . . ?
O4 C20 C16 117.5(3) . . ?
N2 C20 O4 118.1(3) . . ?
N2 C20 C16 124.4(3) . . ?
N2 C21 H21A 110.8 . . ?
N2 C21 H21B 110.8 . . ?
N2 C21 C22 104.6(3) . . ?
H21A C21 H21B 108.9 . . ?
C22 C21 H21A 110.8 . . ?
C22 C21 H21B 110.8 . . ?
O4 C22 C21 103.9(3) . . ?
O4 C22 H22A 111.0 . . ?
O4 C22 H22B 111.0 . . ?
C21 C22 H22A 111.0 . . ?
C21 C22 H22B 111.0 . . ?
H22A C22 H22B 109.0 . . ?
O2 C23 C13 112.3(2) . . ?
O3 C23 O2 124.0(3) . . ?
O3 C23 C13 123.7(3) . . ?
O2 C24 H24A 109.6 . . ?
O2 C24 H24B 109.6 . . ?
O2 C24 C25 110.1(3) . . ?
H24A C24 H24B 108.2 . . ?
C25 C24 H24A 109.6 . . ?
C25 C24 H24B 109.6 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
O1 C10 1.206(4) . ?
O2 C23 1.319(4) . ?
O2 C24 1.461(4) . ?
O3 C23 1.198(3) . ?
O4 C20 1.334(4) . ?
O4 C22 1.446(4) . ?
N1 C1 1.416(4) . ?
N1 C7 1.452(4) . ?
N1 C10 1.378(4) . ?
N2 C20 1.262(4) . ?
N2 C21 1.465(5) . ?
C1 C2 1.383(5) . ?
C1 C6 1.389(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.367(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.364(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.362(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(4) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.526(4) . ?
C8 H8 0.9800 . ?
C8 C9 1.543(4) . ?
C8 C13 1.530(4) . ?
C9 C10 1.517(5) . ?
C9 C11 1.529(5) . ?
C9 C12 1.532(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13 0.9800 . ?
C13 C14 1.528(4) . ?
C13 C23 1.510(4) . ?
C14 C15 1.380(4) . ?
C14 C19 1.384(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.393(4) . ?
C16 C17 1.381(4) . ?
C16 C20 1.470(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.369(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(5) . ?
C19 H19 0.9300 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.509(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.470(6) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
N1 C1 C2 C3 -176.5(3) . . . . ?
N1 C1 C6 C5 177.6(3) . . . . ?
N1 C7 C8 C9 24.7(3) . . . . ?
N1 C7 C8 C13 152.8(2) . . . . ?
N2 C21 C22 O4 3.5(4) . . . . ?
C1 N1 C7 C8 176.9(2) . . . . ?
C1 N1 C10 O1 -12.4(6) . . . . ?
C1 N1 C10 C9 164.8(3) . . . . ?
C1 C2 C3 C4 -1.9(7) . . . . ?
C2 C1 C6 C5 -0.9(5) . . . . ?
C2 C3 C4 C5 0.7(7) . . . . ?
C3 C4 C5 C6 0.4(7) . . . . ?
C4 C5 C6 C1 -0.3(6) . . . . ?
C6 C1 C2 C3 2.0(5) . . . . ?
C7 N1 C1 C2 175.6(3) . . . . ?
C7 N1 C1 C6 -2.9(4) . . . . ?
C7 N1 C10 O1 178.0(4) . . . . ?
C7 N1 C10 C9 -4.9(3) . . . . ?
C7 C8 C9 C10 -26.8(3) . . . . ?
C7 C8 C9 C11 87.5(3) . . . . ?
C7 C8 C9 C12 -145.4(3) . . . . ?
C7 C8 C13 C14 55.3(3) . . . . ?
C7 C8 C13 C23 177.3(2) . . . . ?
C8 C9 C10 O1 -162.6(4) . . . . ?
C8 C9 C10 N1 20.2(3) . . . . ?
C8 C13 C14 C15 63.0(3) . . . . ?
C8 C13 C14 C19 -118.3(3) . . . . ?
C8 C13 C23 O2 130.6(3) . . . . ?
C8 C13 C23 O3 -51.6(4) . . . . ?
C9 C8 C13 C14 175.6(2) . . . . ?
C9 C8 C13 C23 -62.4(3) . . . . ?
C10 N1 C1 C2 6.9(5) . . . . ?
C10 N1 C1 C6 -171.6(3) . . . . ?
C10 N1 C7 C8 -12.9(3) . . . . ?
C11 C9 C10 O1 77.7(4) . . . . ?
C11 C9 C10 N1 -99.5(3) . . . . ?
C12 C9 C10 O1 -40.9(5) . . . . ?
C12 C9 C10 N1 142.0(3) . . . . ?
C13 C8 C9 C10 -151.3(2) . . . . ?
C13 C8 C9 C11 -37.0(3) . . . . ?
C13 C8 C9 C12 90.1(3) . . . . ?
C13 C14 C15 C16 176.8(2) . . . . ?
C13 C14 C19 C18 -178.1(3) . . . . ?
C14 C13 C23 O2 -104.7(3) . . . . ?
C14 C13 C23 O3 73.1(4) . . . . ?
C14 C15 C16 C17 2.0(4) . . . . ?
C14 C15 C16 C20 -177.9(3) . . . . ?
C15 C14 C19 C18 0.7(5) . . . . ?
C15 C16 C17 C18 -0.8(5) . . . . ?
C15 C16 C20 O4 175.2(3) . . . . ?
C15 C16 C20 N2 -4.1(4) . . . . ?
C16 C17 C18 C19 -0.4(6) . . . . ?
C17 C16 C20 O4 -4.7(4) . . . . ?
C17 C16 C20 N2 176.0(3) . . . . ?
C17 C18 C19 C14 0.4(6) . . . . ?
C19 C14 C15 C16 -1.9(4) . . . . ?
C20 O4 C22 C21 -3.3(4) . . . . ?
C20 N2 C21 C22 -2.6(4) . . . . ?
C20 C16 C17 C18 179.1(3) . . . . ?
C21 N2 C20 O4 0.6(4) . . . . ?
C21 N2 C20 C16 179.9(3) . . . . ?
C22 O4 C20 N2 1.8(4) . . . . ?
C22 O4 C20 C16 -177.5(3) . . . . ?
C23 O2 C24 C25 90.7(4) . . . . ?
C23 C13 C14 C15 -61.4(3) . . . . ?
C23 C13 C14 C19 117.3(3) . . . . ?
C24 O2 C23 O3 3.7(5) . . . . ?
C24 O2 C23 C13 -178.5(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168346979
