#------------------------------------------------------------------------------
#$Date: 2022-04-13 01:13:22 +0300 (Wed, 13 Apr 2022) $
#$Revision: 274496 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/67/1566785.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_1566785
loop_
_publ_author_name
'Liu, Hong-Chao'
'Kong, Xiangtao'
'Gong, Xiao-Ping'
'Li, Yuke'
'Niu, Zhi-Jie'
'Gou, Xue-Ya'
'Li, Xue-Song'
'Wang, Yu-Zhao'
'Shi, Wei-Yu'
'Huang, Yan-Chong'
'Liu, Xue-Yuan'
'Liang, Yong-Min'
_publ_section_title
;
 Site-Selective Coupling of Remote C(sp3)−H/meta-C(sp2)−H
 Bonds Enabled by Ru/Photoredox Dual Catalysis and Mechanistic Studies
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC00764A
_journal_year                    2022
_chemical_formula_moiety         'C22 H30 N2 O2'
_chemical_formula_sum            'C22 H30 N2 O2'
_chemical_formula_weight         354.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2021-08-30 deposited with the CCDC.	2022-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.028(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.4831(8)
_cell_length_b                   10.8800(4)
_cell_length_c                   9.8987(3)
_cell_measurement_reflns_used    5882
_cell_measurement_temperature    302.58(10)
_cell_measurement_theta_max      73.8040
_cell_measurement_theta_min      2.3050
_cell_volume                     2072.29(13)
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      302.58(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     39.00  71.00   0.50    1.20    --  104.25 -61.00  30.00   64
  2  ω     93.00 168.00   0.50    1.20    --  104.25  45.00 -90.00  150
  3  ω    101.00 165.00   0.50    1.20    --  104.25  45.00-150.00  128
  4  ω    -24.00  26.00   0.50    0.50    --   46.32 -19.00-180.00  100
  5  ω     40.00  65.00   0.50    1.20    --  104.25 -77.00-180.00   50
  6  ω     70.00 106.00   0.50    1.20    --  104.25 -77.00-180.00   72
  7  ω     29.00  63.00   0.50    0.50    --   46.32-137.00-147.00   68
  8  ω     32.00 115.00   0.50    1.20    --  104.25-131.00  28.00  166
  9  ω     37.00 111.00   0.50    1.20    --  104.25-125.00  60.00  148
 10  ω     41.00  88.00   0.50    1.20    --  104.25 -94.00  90.00   94
 11  ω     25.00  96.00   0.50    0.50    --   46.32-131.00  28.00  142
 12  ω     52.00  77.00   0.50    1.20    --  104.25-137.00-147.00   50
 13  ω    -25.00  28.00   0.50    0.50    --  -46.32  19.00-120.00  106
 14  ω    -85.00 -60.00   0.50    0.50    --  -46.32 137.00 -85.00   50
 15  ω    -69.00 -31.00   0.50    1.20    -- -102.00  61.00-150.00   76
 16  ω    -81.00 -56.00   0.50    0.50    --  -46.32 131.00  98.00   50
 17  ω   -113.00 -37.00   0.50    1.20    -- -102.00 131.00  98.00  152
 18  ω    -55.00 -30.00   0.50    1.20    -- -102.00  61.00  30.00   50
 19  ω   -127.00 -86.00   0.50    1.20    -- -102.00 -61.00 -60.00   82
 20  ω   -115.00 -90.00   0.50    0.50    --  -46.32-125.00 -90.00   50
 21  ω   -114.00 -88.00   0.50    0.50    --  -46.32-137.00-147.00   52
 22  ω   -100.00 -74.00   0.50    0.50    --  -46.32-131.00  28.00   52
 23  ω   -118.00 -75.00   0.50    0.50    --  -46.32-125.00  60.00   86
 24  ω   -119.00 -74.00   0.50    0.50    --  -46.32-125.00 150.00   90
 25  ω   -173.00-140.00   0.50    1.20    -- -102.00 -61.00 -60.00   66
 26  ω   -147.00-122.00   0.50    1.20    -- -102.00-131.00  28.00   50
 27  ω   -101.00 -68.00   0.50    1.20    -- -102.00-137.00-147.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0712729000
_diffrn_orient_matrix_UB_12      -0.0644394000
_diffrn_orient_matrix_UB_13      -0.0247382000
_diffrn_orient_matrix_UB_21      0.0364326000
_diffrn_orient_matrix_UB_22      -0.1260290000
_diffrn_orient_matrix_UB_23      0.0168213000
_diffrn_orient_matrix_UB_31      -0.0025268000
_diffrn_orient_matrix_UB_32      0.0033556000
_diffrn_orient_matrix_UB_33      0.1546971000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0834
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            15890
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.210
_diffrn_reflns_theta_min         2.296
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.570
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68015
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
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    1.136
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         15890
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0771
_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)+(0.1262P)²+0.6353P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2360
_refine_ls_wR_factor_ref         0.2523
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11742
_reflns_number_total             15890
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc00764a2.cif
_cod_data_source_block           liuhongchao_0830-1_auto
_cod_database_code               1566785
_shelx_shelxl_version_number     2018/1
_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 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.768(6)
 0.232(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B)
3.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C3(H3A), C4(H4), C5(H5), C8(H8), C10(H10), C12(H12)
3.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C20(H20A,H20B,
 H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_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 2.311
_oxdiff_exptl_absorpt_empirical_full_min 0.350
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.29314(16) 0.5802(3) 0.3521(2) 0.0819(9) Uani 1 1 d . . . . .
O2 O 0.15089(15) 0.7430(2) 0.5959(2) 0.0756(8) Uani 1 1 d . . . . .
N3 N 0.12000(14) 0.7997(2) 0.7957(2) 0.0511(7) Uani 1 1 d . . . . .
H3 H 0.126377 0.785396 0.882177 0.061 Uiso 1 1 calc R U . . .
C1 C 0.44829(17) 0.2661(3) 0.5940(3) 0.0553(8) Uani 1 1 d . . . . .
C2 C 0.5050(2) 0.2945(4) 0.5316(5) 0.0828(12) Uani 1 1 d . . . . .
H2 H 0.505724 0.366093 0.480410 0.099 Uiso 1 1 calc R U . . .
C3 C 0.5615(3) 0.2123(6) 0.5474(6) 0.1085(17) Uani 1 1 d . . . . .
H3A H 0.600062 0.228314 0.505611 0.130 Uiso 1 1 calc R U . . .
C4 C 0.5591(3) 0.1090(5) 0.6247(6) 0.1018(15) Uani 1 1 d . . . . .
H4 H 0.596199 0.054102 0.638116 0.122 Uiso 1 1 calc R U . . .
C5 C 0.5019(3) 0.0890(5) 0.6806(5) 0.1004(15) Uani 1 1 d . . . . .
H5 H 0.500391 0.017874 0.732154 0.120 Uiso 1 1 calc R U . . .
N6 N 0.44687(19) 0.1634(3) 0.6680(4) 0.0820(10) Uani 1 1 d . . . . .
C7 C 0.38708(16) 0.3484(3) 0.5814(3) 0.0497(7) Uani 1 1 d . . . . .
C8 C 0.37132(18) 0.4267(3) 0.4685(3) 0.0562(8) Uani 1 1 d . . . . .
H8 H 0.399869 0.429013 0.401552 0.067 Uiso 1 1 calc R U . . .
C9 C 0.31318(19) 0.5003(3) 0.4575(3) 0.0564(8) Uani 1 1 d . . . . .
C10 C 0.26978(18) 0.4972(3) 0.5555(3) 0.0542(8) Uani 1 1 d . . . . .
H10 H 0.230977 0.548099 0.546390 0.065 Uiso 1 1 calc R U . . .
C11 C 0.28351(16) 0.4189(2) 0.6673(3) 0.0457(7) Uani 1 1 d . . . . .
C12 C 0.34278(16) 0.3450(3) 0.6778(3) 0.0488(7) Uani 1 1 d . . . . .
H12 H 0.352790 0.291928 0.751926 0.059 Uiso 1 1 calc R U . . .
C13 C 0.3267(3) 0.5739(5) 0.2355(4) 0.0936(14) Uani 1 1 d . . . . .
H13A H 0.301841 0.623333 0.163604 0.140 Uiso 1 1 calc R U . . .
H13B H 0.327622 0.490148 0.205339 0.140 Uiso 1 1 calc R U . . .
H13C H 0.373403 0.603967 0.258354 0.140 Uiso 1 1 calc R U . . .
C14 C 0.23325(17) 0.4061(3) 0.7721(3) 0.0513(7) Uani 1 1 d . . . . .
C15 C 0.2728(2) 0.4051(4) 0.9174(3) 0.0689(10) Uani 1 1 d . . . . .
H15A H 0.302970 0.334872 0.929509 0.103 Uiso 1 1 calc R U . . .
H15B H 0.240372 0.400840 0.981011 0.103 Uiso 1 1 calc R U . . .
H15C H 0.299889 0.478789 0.933393 0.103 Uiso 1 1 calc R U . . .
C16 C 0.1948(2) 0.2835(3) 0.7430(5) 0.0825(12) Uani 1 1 d . . . . .
H16A H 0.168522 0.285032 0.652432 0.124 Uiso 1 1 calc R U . . .
H16B H 0.163928 0.271241 0.808405 0.124 Uiso 1 1 calc R U . . .
H16C H 0.227917 0.217581 0.749868 0.124 Uiso 1 1 calc R U . . .
C17 C 0.17827(16) 0.5085(3) 0.7581(3) 0.0519(8) Uani 1 1 d . . . . .
H17A H 0.154454 0.509050 0.664407 0.062 Uiso 1 1 calc R U . . .
H17B H 0.144170 0.487956 0.816151 0.062 Uiso 1 1 calc R U . . .
C18 C 0.20502(17) 0.6386(3) 0.7945(3) 0.0510(7) Uani 1 1 d . . . . .
H18A H 0.208759 0.651191 0.892390 0.061 Uiso 1 1 calc R U . . .
H18B H 0.250913 0.648378 0.769574 0.061 Uiso 1 1 calc R U . . .
C19 C 0.15649(17) 0.7326(3) 0.7203(3) 0.0482(7) Uani 1 1 d . . . . .
C20 C 0.0102(3) 0.8418(5) 0.6447(6) 0.1043(16) Uani 1 1 d . . . . .
H20A H 0.028025 0.807285 0.567887 0.156 Uiso 1 1 calc R U . . .
H20B H -0.022542 0.905546 0.613547 0.156 Uiso 1 1 calc R U . . .
H20C H -0.012392 0.778760 0.689294 0.156 Uiso 1 1 calc R U . . .
C21 C 0.06993(19) 0.8956(3) 0.7450(3) 0.0577(9) Uani 1 1 d . . . . .
C22 C 0.1050(3) 0.9946(4) 0.6737(6) 0.1052(16) Uani 1 1 d . . . . .
H22A H 0.140794 1.032618 0.737932 0.158 Uiso 1 1 calc R U . . .
H22B H 0.071390 1.055270 0.637373 0.158 Uiso 1 1 calc R U . . .
H22C H 0.125266 0.958746 0.600554 0.158 Uiso 1 1 calc R U . . .
C23 C 0.0425(4) 0.9481(7) 0.8674(5) 0.143(3) Uani 1 1 d . . . . .
H23A H 0.021016 0.883914 0.912489 0.215 Uiso 1 1 calc R U . . .
H23B H 0.008905 1.010861 0.837626 0.215 Uiso 1 1 calc R U . . .
H23C H 0.080238 0.982862 0.929710 0.215 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 0.0181 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
C9 O1 C13 118.6(3) . . ?
C19 N3 H3 117.0 . . ?
C19 N3 C21 126.0(2) . . ?
C21 N3 H3 117.0 . . ?
C2 C1 C7 121.0(3) . . ?
N6 C1 C2 121.2(3) . . ?
N6 C1 C7 117.8(3) . . ?
C1 C2 H2 120.9 . . ?
C1 C2 C3 118.2(4) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 C2 119.5(4) . . ?
C4 C3 H3A 120.3 . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 117.9(4) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 H5 117.5 . . ?
N6 C5 C4 125.0(5) . . ?
N6 C5 H5 117.5 . . ?
C5 N6 C1 118.2(4) . . ?
C8 C7 C1 120.5(3) . . ?
C12 C7 C1 120.4(3) . . ?
C12 C7 C8 119.0(3) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 H8 120.3 . . ?
O1 C9 C8 124.3(3) . . ?
O1 C9 C10 114.7(3) . . ?
C8 C9 C10 121.0(3) . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.7(3) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C12 117.7(3) . . ?
C10 C11 C14 121.9(3) . . ?
C12 C11 C14 120.2(3) . . ?
C7 C12 C11 122.1(3) . . ?
C7 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C11 110.9(3) . . ?
C15 C14 C16 109.3(3) . . ?
C15 C14 C17 109.4(2) . . ?
C16 C14 C11 107.2(2) . . ?
C16 C14 C17 107.5(3) . . ?
C17 C14 C11 112.5(2) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 108.2 . . ?
C14 C17 H17B 108.2 . . ?
H17A C17 H17B 107.4 . . ?
C18 C17 C14 116.2(3) . . ?
C18 C17 H17A 108.2 . . ?
C18 C17 H17B 108.2 . . ?
C17 C18 H18A 109.6 . . ?
C17 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
C19 C18 C17 110.4(3) . . ?
C19 C18 H18A 109.6 . . ?
C19 C18 H18B 109.6 . . ?
O2 C19 N3 122.9(3) . . ?
O2 C19 C18 120.3(3) . . ?
N3 C19 C18 116.8(2) . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
N3 C21 C20 110.4(3) . . ?
N3 C21 C22 110.0(3) . . ?
N3 C21 C23 107.2(3) . . ?
C22 C21 C20 109.0(4) . . ?
C22 C21 C23 110.4(4) . . ?
C23 C21 C20 109.8(5) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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 C9 1.368(4) . ?
O1 C13 1.415(5) . ?
O2 C19 1.224(3) . ?
N3 H3 0.8600 . ?
N3 C19 1.327(4) . ?
N3 C21 1.463(4) . ?
C1 C2 1.383(5) . ?
C1 N6 1.338(5) . ?
C1 C7 1.481(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.408(7) . ?
C3 H3A 0.9300 . ?
C3 C4 1.365(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.338(7) . ?
C5 H5 0.9300 . ?
C5 N6 1.333(5) . ?
C7 C8 1.400(4) . ?
C7 C12 1.384(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.377(5) . ?
C9 C10 1.384(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.389(4) . ?
C11 C12 1.397(4) . ?
C11 C14 1.540(4) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.522(5) . ?
C14 C16 1.535(5) . ?
C14 C17 1.536(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.532(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.504(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20 C21 1.523(6) . ?
C21 C22 1.509(6) . ?
C21 C23 1.510(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
O1 C9 C10 C11 179.2(3) . . . . ?
C1 C2 C3 C4 -0.9(8) . . . . ?
C1 C7 C8 C9 178.5(3) . . . . ?
C1 C7 C12 C11 -178.2(3) . . . . ?
C2 C1 N6 C5 0.3(6) . . . . ?
C2 C1 C7 C8 25.7(5) . . . . ?
C2 C1 C7 C12 -157.3(3) . . . . ?
C2 C3 C4 C5 1.2(9) . . . . ?
C3 C4 C5 N6 -0.8(9) . . . . ?
C4 C5 N6 C1 0.0(8) . . . . ?
N6 C1 C2 C3 0.1(6) . . . . ?
N6 C1 C7 C8 -154.3(3) . . . . ?
N6 C1 C7 C12 22.7(4) . . . . ?
C7 C1 C2 C3 -179.9(4) . . . . ?
C7 C1 N6 C5 -179.6(4) . . . . ?
C7 C8 C9 O1 179.7(3) . . . . ?
C7 C8 C9 C10 -0.6(5) . . . . ?
C8 C7 C12 C11 -1.2(4) . . . . ?
C8 C9 C10 C11 -0.5(5) . . . . ?
C9 C10 C11 C12 0.7(4) . . . . ?
C9 C10 C11 C14 -175.2(3) . . . . ?
C10 C11 C12 C7 0.1(4) . . . . ?
C10 C11 C14 C15 -136.5(3) . . . . ?
C10 C11 C14 C16 104.3(3) . . . . ?
C10 C11 C14 C17 -13.6(4) . . . . ?
C11 C14 C17 C18 -67.1(3) . . . . ?
C12 C7 C8 C9 1.4(4) . . . . ?
C12 C11 C14 C15 47.7(4) . . . . ?
C12 C11 C14 C16 -71.6(4) . . . . ?
C12 C11 C14 C17 170.5(3) . . . . ?
C13 O1 C9 C8 10.9(5) . . . . ?
C13 O1 C9 C10 -168.7(4) . . . . ?
C14 C11 C12 C7 176.1(3) . . . . ?
C14 C17 C18 C19 154.5(3) . . . . ?
C15 C14 C17 C18 56.6(4) . . . . ?
C16 C14 C17 C18 175.2(3) . . . . ?
C17 C18 C19 O2 -68.2(4) . . . . ?
C17 C18 C19 N3 110.3(3) . . . . ?
C19 N3 C21 C20 61.5(5) . . . . ?
C19 N3 C21 C22 -58.8(4) . . . . ?
C19 N3 C21 C23 -178.9(5) . . . . ?
C21 N3 C19 O2 -1.4(5) . . . . ?
C21 N3 C19 C18 -179.9(3) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.768(6)
2 0.232(6)
