#------------------------------------------------------------------------------
#$Date: 2021-11-06 20:47:16 +0200 (Sat, 06 Nov 2021) $
#$Revision: 270359 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/89/7128975.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_7128975
loop_
_publ_author_name
'Bhat, Aabid'
'Tucker, Nathan'
'Lin, Jian-Bin'
'Grover, Huck'
_publ_section_title
;
 Stereoselective copper-catalyzed heteroarene C-H
 functionalization/Michael-type annulation cascade with α-diazocarbonyls.
;
_journal_issue                   81
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              10556
_journal_page_last               10559
_journal_paper_doi               10.1039/d1cc04590c
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C23 H27 N O7'
_chemical_formula_sum            'C23 H27 N O7'
_chemical_formula_weight         429.45
_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             2020-11-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-08-04 deposited with the CCDC.	2021-09-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.3152(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.27378(13)
_cell_length_b                   17.12971(15)
_cell_length_c                   9.94500(9)
_cell_measurement_reflns_used    10349
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.1660
_cell_measurement_theta_min      3.4260
_cell_volume                     2191.04(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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  26.00   0.50    0.08    --  -47.95  19.00 -60.00   76
  2  ω    -16.00  21.00   0.50    0.08    --  -47.95  19.00 -90.00   74
  3  ω    -43.00 -14.00   0.50    0.33    --  -86.25  45.00-150.00   58
  4  ω    -80.00   2.00   0.50    0.08    --  -47.95 100.00  35.00  164
  5  ω     31.00  58.00   0.50    0.08    --   47.95-100.00 -69.00   54
  6  ω     64.00 106.00   0.50    0.33    --  107.75-100.00 -69.00   84
  7  ω     81.00 106.00   0.50    0.33    --  107.75 -94.00 -30.00   50
  8  ω     50.00  78.00   0.50    0.33    --  107.75 -61.00 -60.00   56
  9  ω     35.00  60.00   0.50    0.33    --  107.75 -94.00 -30.00   50
 10  ω     46.00  79.00   0.50    0.33    --  107.75 -61.00 -30.00   66
 11  ω     37.00  71.00   0.50    0.33    --  107.75 -61.00  30.00   68
 12  ω     53.00  79.00   0.50    0.33    --  107.75 -61.00  60.00   52
 13  ω     39.00  79.00   0.50    0.33    --  107.75 -61.00  90.00   80
 14  ω     36.00  78.00   0.50    0.33    --  107.75 -61.00 150.00   84
 15  ω     36.00  76.00   0.50    0.33    --  107.75-125.00  90.00   80
 16  ω     83.00 110.00   0.50    0.33    --  107.75-125.00  90.00   54
 17  ω     39.00  65.00   0.50    0.33    --  107.75 -94.00  30.00   52
 18  ω     97.00 167.00   0.50    0.33    --  107.75  30.00  90.00  140
 19  ω    140.00 173.00   0.50    0.33    --  107.75  77.00 150.00   66
 20  ω    152.00 178.00   0.50    0.33    --  107.75 125.00  90.00   52
 21  ω    122.00 147.00   0.50    0.33    --  107.75 125.00  90.00   50
 22  ω    112.00 165.00   0.50    0.33    --  107.75 100.00  35.00  106
 23  ω    153.00 178.00   0.50    0.33    --  107.75  61.00 -30.00   50
 24  ω    149.00 174.00   0.50    0.33    --  107.75  61.00 -90.00   50
 25  ω    109.00 135.00   0.50    0.33    --  107.75  61.00 -90.00   52
 26  ω     97.00 143.00   0.50    0.33    --  107.75  61.00 -30.00   92
 27  ω     96.00 165.00   0.50    0.33    --  107.75 125.00  60.00  138
 28  ω     86.00 123.00   0.50    0.33    --  107.75  77.00 150.00   74
 29  ω    -13.00  27.00   0.50    0.08    --  -47.95  19.00 150.00   80
 30  ω    -71.00 -46.00   0.50    0.33    --  -86.25 100.00  35.00   50
 31  ω   -130.00-105.00   0.50    0.33    --  -86.25-100.00 -69.00   50
 32  ω   -120.00 -95.00   0.50    0.08    --  -47.95-125.00  60.00   50
 33  ω   -118.00 -73.00   0.50    0.08    --  -47.95-125.00  90.00   90
 34  ω     38.00  63.00   0.50    0.33    --  107.75 -61.00-180.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0310449000
_diffrn_orient_matrix_UB_12      0.0817866000
_diffrn_orient_matrix_UB_13      0.0400679000
_diffrn_orient_matrix_UB_21      -0.1148065000
_diffrn_orient_matrix_UB_22      -0.0254190000
_diffrn_orient_matrix_UB_23      -0.0336460000
_diffrn_orient_matrix_UB_31      0.0140567000
_diffrn_orient_matrix_UB_32      -0.0274268000
_diffrn_orient_matrix_UB_33      0.1511267000
_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  0.0550
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            19064
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.343
_diffrn_reflns_theta_min         3.436
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.801
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60225
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       irregular
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.199
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.00083(18)
_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   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4580
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0402
_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)+(0.0458P)²+0.6602P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1069
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3981
_reflns_number_total             4580
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc04590c2.cif
_cod_data_source_block           ahb-a-106
_cod_depositor_comments
'Adding full bibliography for 7128973--7128976.cif.'
_cod_database_code               7128975
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C23H27NO7
_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   0.943
_shelx_estimated_absorpt_t_min   0.857
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C16(H16A,H16B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C21(H21)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C17(H17A,H17B,H17C), C20(H20A,H20B,
 H20C), 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 1.601
_oxdiff_exptl_absorpt_empirical_full_min 0.395
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 0.37993(8) 0.62286(6) 0.82149(9) 0.0256(2) Uani 1 1 d . . . . .
O2 O 0.39405(7) 0.45099(5) 0.38991(9) 0.0204(2) Uani 1 1 d . . . . .
O3 O 0.37889(7) 0.54964(5) 0.23637(9) 0.0202(2) Uani 1 1 d . . . . .
O4 O 0.14360(7) 0.58822(6) 0.08717(9) 0.0218(2) Uani 1 1 d . . . . .
O5 O 0.20275(7) 0.63127(5) 0.30601(9) 0.0192(2) Uani 1 1 d . . . . .
O6 O 0.13753(9) 0.30252(6) -0.05391(11) 0.0313(2) Uani 1 1 d . . . . .
O7 O 0.31147(9) 0.29411(6) -0.00461(13) 0.0370(3) Uani 1 1 d . . . . .
N1 N 0.09028(9) 0.41685(7) 0.52721(11) 0.0211(2) Uani 1 1 d . . . . .
C1 C 0.15795(10) 0.46675(8) 0.61521(13) 0.0195(3) Uani 1 1 d . . . . .
C2 C 0.17254(11) 0.47969(8) 0.75733(14) 0.0226(3) Uani 1 1 d . . . . .
H2 H 0.132074 0.452639 0.808894 0.027 Uiso 1 1 calc R U . . .
C3 C 0.24722(11) 0.53274(8) 0.82072(13) 0.0230(3) Uani 1 1 d . . . . .
H3 H 0.258711 0.542273 0.917433 0.028 Uiso 1 1 calc R U . . .
C4 C 0.30686(10) 0.57309(8) 0.74374(13) 0.0203(3) Uani 1 1 d . . . . .
C5 C 0.29186(10) 0.56157(7) 0.60227(13) 0.0178(3) Uani 1 1 d . . . . .
H5 H 0.331212 0.589969 0.550898 0.021 Uiso 1 1 calc R U . . .
C6 C 0.21696(10) 0.50684(7) 0.53682(13) 0.0167(3) Uani 1 1 d . . . . .
C7 C 0.18185(10) 0.47859(7) 0.39729(12) 0.0167(3) Uani 1 1 d . . . . .
C8 C 0.22217(10) 0.49647(7) 0.27061(12) 0.0160(3) Uani 1 1 d . . . . .
C9 C 0.18224(10) 0.43202(7) 0.16270(12) 0.0180(3) Uani 1 1 d . . . . .
C10 C 0.06821(10) 0.41483(8) 0.14137(14) 0.0223(3) Uani 1 1 d . . . . .
H10A H 0.045893 0.377503 0.063697 0.027 Uiso 1 1 calc R U . . .
H10B H 0.027883 0.463582 0.116325 0.027 Uiso 1 1 calc R U . . .
C11 C 0.04546(10) 0.38011(8) 0.27353(14) 0.0230(3) Uani 1 1 d . . . . .
H11A H -0.029921 0.383267 0.268045 0.028 Uiso 1 1 calc R U . . .
H11B H 0.066401 0.324513 0.282743 0.028 Uiso 1 1 calc R U . . .
C12 C 0.10490(10) 0.42497(7) 0.39586(13) 0.0190(3) Uani 1 1 d . . . . .
C13 C 0.01631(11) 0.36462(9) 0.56670(16) 0.0274(3) Uani 1 1 d . . . . .
H13A H -0.052969 0.388419 0.542501 0.041 Uiso 1 1 calc R U . . .
H13B H 0.037457 0.355239 0.666960 0.041 Uiso 1 1 calc R U . . .
H13C H 0.014534 0.314943 0.517274 0.041 Uiso 1 1 calc R U . . .
C14 C 0.43698(11) 0.67052(8) 0.74920(15) 0.0264(3) Uani 1 1 d . . . . .
H14A H 0.388919 0.704555 0.684240 0.040 Uiso 1 1 calc R U . . .
H14B H 0.474516 0.637294 0.697729 0.040 Uiso 1 1 calc R U . . .
H14C H 0.486775 0.702533 0.815863 0.040 Uiso 1 1 calc R U . . .
C15 C 0.34181(10) 0.49625(7) 0.30925(12) 0.0161(2) Uani 1 1 d . . . . .
C16 C 0.49162(10) 0.54803(9) 0.25349(15) 0.0254(3) Uani 1 1 d . . . . .
H16A H 0.512045 0.499494 0.213075 0.030 Uiso 1 1 calc R U . . .
H16B H 0.527696 0.549539 0.353295 0.030 Uiso 1 1 calc R U . . .
C17 C 0.52106(13) 0.61746(11) 0.1812(2) 0.0388(4) Uani 1 1 d . . . . .
H17A H 0.482349 0.616825 0.083527 0.058 Uiso 1 1 calc R U . . .
H17B H 0.595823 0.615982 0.186974 0.058 Uiso 1 1 calc R U . . .
H17C H 0.504368 0.665201 0.225481 0.058 Uiso 1 1 calc R U . . .
C18 C 0.18412(10) 0.57646(7) 0.20744(12) 0.0164(2) Uani 1 1 d . . . . .
C19 C 0.17494(11) 0.71079(7) 0.26086(13) 0.0208(3) Uani 1 1 d . . . . .
H19A H 0.100495 0.713798 0.211522 0.025 Uiso 1 1 calc R U . . .
H19B H 0.217012 0.728751 0.197344 0.025 Uiso 1 1 calc R U . . .
C20 C 0.19637(12) 0.76039(8) 0.38911(14) 0.0253(3) Uani 1 1 d . . . . .
H20A H 0.179309 0.814894 0.363227 0.038 Uiso 1 1 calc R U . . .
H20B H 0.270091 0.756384 0.437388 0.038 Uiso 1 1 calc R U . . .
H20C H 0.153718 0.742301 0.450514 0.038 Uiso 1 1 calc R U . . .
C21 C 0.24752(11) 0.39414(8) 0.10261(13) 0.0193(3) Uani 1 1 d . . . . .
H21 H 0.317342 0.412181 0.123480 0.023 Uiso 1 1 calc R U . . .
C22 C 0.22191(11) 0.32678(8) 0.00666(13) 0.0221(3) Uani 1 1 d . . . . .
C23 C 0.30083(17) 0.22650(12) -0.0941(3) 0.0625(7) Uani 1 1 d . . . . .
H23A H 0.257643 0.239884 -0.186174 0.094 Uiso 1 1 calc R U . . .
H23B H 0.267949 0.183999 -0.054510 0.094 Uiso 1 1 calc R U . . .
H23C H 0.369697 0.209800 -0.102197 0.094 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
C4 O1 C14 117.42(10) . . ?
C15 O3 C16 115.32(10) . . ?
C18 O5 C19 116.45(9) . . ?
C22 O7 C23 115.54(13) . . ?
C1 N1 C13 125.88(11) . . ?
C12 N1 C1 108.45(11) . . ?
C12 N1 C13 125.67(12) . . ?
N1 C1 C2 130.11(12) . . ?
N1 C1 C6 108.25(11) . . ?
C2 C1 C6 121.64(12) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.17(12) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.79(12) . . ?
C4 C3 H3 119.6 . . ?
O1 C4 C3 114.24(11) . . ?
O1 C4 C5 124.27(12) . . ?
C5 C4 C3 121.48(13) . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.26(12) . . ?
C6 C5 H5 120.9 . . ?
C1 C6 C7 106.15(11) . . ?
C5 C6 C1 119.64(11) . . ?
C5 C6 C7 134.21(11) . . ?
C6 C7 C8 129.68(11) . . ?
C12 C7 C6 107.40(11) . . ?
C12 C7 C8 122.79(11) . . ?
C7 C8 C9 107.63(10) . . ?
C7 C8 C15 110.27(10) . . ?
C7 C8 C18 111.78(10) . . ?
C9 C8 C18 109.39(10) . . ?
C15 C8 C9 109.18(10) . . ?
C15 C8 C18 108.56(10) . . ?
C10 C9 C8 113.55(11) . . ?
C21 C9 C8 120.69(12) . . ?
C21 C9 C10 125.66(12) . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C9 C10 C11 110.99(11) . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C10 C11 H11A 109.9 . . ?
C10 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 C10 108.79(11) . . ?
C12 C11 H11A 109.9 . . ?
C12 C11 H11B 109.9 . . ?
N1 C12 C11 123.60(12) . . ?
C7 C12 N1 109.74(11) . . ?
C7 C12 C11 126.65(12) . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 O3 125.04(12) . . ?
O2 C15 C8 123.82(11) . . ?
O3 C15 C8 111.05(10) . . ?
O3 C16 H16A 110.1 . . ?
O3 C16 H16B 110.1 . . ?
O3 C16 C17 108.13(12) . . ?
H16A C16 H16B 108.4 . . ?
C17 C16 H16A 110.1 . . ?
C17 C16 H16B 110.1 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 O5 124.69(12) . . ?
O4 C18 C8 125.21(11) . . ?
O5 C18 C8 110.09(10) . . ?
O5 C19 H19A 110.4 . . ?
O5 C19 H19B 110.4 . . ?
O5 C19 C20 106.74(10) . . ?
H19A C19 H19B 108.6 . . ?
C20 C19 H19A 110.4 . . ?
C20 C19 H19B 110.4 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C9 C21 H21 116.7 . . ?
C9 C21 C22 126.52(12) . . ?
C22 C21 H21 116.7 . . ?
O6 C22 O7 123.11(12) . . ?
O6 C22 C21 128.76(13) . . ?
O7 C22 C21 108.13(11) . . ?
O7 C23 H23A 109.5 . . ?
O7 C23 H23B 109.5 . . ?
O7 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 C4 1.3764(17) . ?
O1 C14 1.4234(18) . ?
O2 C15 1.2042(16) . ?
O3 C15 1.3343(15) . ?
O3 C16 1.4638(15) . ?
O4 C18 1.2010(15) . ?
O5 C18 1.3355(15) . ?
O5 C19 1.4530(15) . ?
O6 C22 1.2068(18) . ?
O7 C22 1.3435(18) . ?
O7 C23 1.4459(19) . ?
N1 C1 1.3837(18) . ?
N1 C12 1.3744(17) . ?
N1 C13 1.4524(17) . ?
C1 C2 1.3960(19) . ?
C1 C6 1.4123(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.377(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.4108(19) . ?
C4 C5 1.3854(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.4040(18) . ?
C6 C7 1.4343(17) . ?
C7 C8 1.5168(16) . ?
C7 C12 1.3711(18) . ?
C8 C9 1.5396(17) . ?
C8 C15 1.5388(17) . ?
C8 C18 1.5397(17) . ?
C9 C10 1.5046(18) . ?
C9 C21 1.3360(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5390(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.4894(19) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.491(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.5001(19) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21 0.9500 . ?
C21 C22 1.4823(18) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
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 C4 C5 C6 177.71(11) . . . . ?
N1 C1 C2 C3 179.17(13) . . . . ?
N1 C1 C6 C5 179.88(11) . . . . ?
N1 C1 C6 C7 -0.15(14) . . . . ?
C1 N1 C12 C7 0.76(15) . . . . ?
C1 N1 C12 C11 179.86(12) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C1 C6 C7 C8 -175.26(12) . . . . ?
C1 C6 C7 C12 0.60(14) . . . . ?
C2 C1 C6 C5 -0.45(19) . . . . ?
C2 C1 C6 C7 179.53(12) . . . . ?
C2 C3 C4 O1 -178.63(12) . . . . ?
C2 C3 C4 C5 0.7(2) . . . . ?
C3 C4 C5 C6 -1.57(19) . . . . ?
C4 C5 C6 C1 1.42(18) . . . . ?
C4 C5 C6 C7 -178.55(13) . . . . ?
C5 C6 C7 C8 4.7(2) . . . . ?
C5 C6 C7 C12 -179.43(14) . . . . ?
C6 C1 C2 C3 -0.43(19) . . . . ?
C6 C7 C8 C9 161.73(12) . . . . ?
C6 C7 C8 C15 42.73(17) . . . . ?
C6 C7 C8 C18 -78.13(16) . . . . ?
C6 C7 C12 N1 -0.84(14) . . . . ?
C6 C7 C12 C11 -179.91(12) . . . . ?
C7 C8 C9 C10 47.28(13) . . . . ?
C7 C8 C9 C21 -129.38(12) . . . . ?
C7 C8 C15 O2 38.17(16) . . . . ?
C7 C8 C15 O3 -145.14(10) . . . . ?
C7 C8 C18 O4 -129.63(13) . . . . ?
C7 C8 C18 O5 50.41(13) . . . . ?
C8 C7 C12 N1 175.37(11) . . . . ?
C8 C7 C12 C11 -3.7(2) . . . . ?
C8 C9 C10 C11 -65.50(14) . . . . ?
C8 C9 C21 C22 174.46(12) . . . . ?
C9 C8 C15 O2 -79.88(14) . . . . ?
C9 C8 C15 O3 96.81(12) . . . . ?
C9 C8 C18 O4 -10.53(17) . . . . ?
C9 C8 C18 O5 169.51(10) . . . . ?
C9 C10 C11 C12 43.36(14) . . . . ?
C9 C21 C22 O6 14.5(2) . . . . ?
C9 C21 C22 O7 -165.55(13) . . . . ?
C10 C9 C21 C22 -1.8(2) . . . . ?
C10 C11 C12 N1 169.88(12) . . . . ?
C10 C11 C12 C7 -11.18(18) . . . . ?
C12 N1 C1 C2 180.00(13) . . . . ?
C12 N1 C1 C6 -0.36(14) . . . . ?
C12 C7 C8 C9 -13.57(16) . . . . ?
C12 C7 C8 C15 -132.57(12) . . . . ?
C12 C7 C8 C18 106.57(13) . . . . ?
C13 N1 C1 C2 -0.1(2) . . . . ?
C13 N1 C1 C6 179.59(12) . . . . ?
C13 N1 C12 C7 -179.19(12) . . . . ?
C13 N1 C12 C11 -0.1(2) . . . . ?
C14 O1 C4 C3 -174.77(12) . . . . ?
C14 O1 C4 C5 5.90(19) . . . . ?
C15 O3 C16 C17 -172.38(12) . . . . ?
C15 C8 C9 C10 166.98(10) . . . . ?
C15 C8 C9 C21 -9.68(16) . . . . ?
C15 C8 C18 O4 108.52(14) . . . . ?
C15 C8 C18 O5 -71.44(12) . . . . ?
C16 O3 C15 O2 3.47(18) . . . . ?
C16 O3 C15 C8 -173.17(10) . . . . ?
C18 O5 C19 C20 176.46(11) . . . . ?
C18 C8 C9 C10 -74.36(13) . . . . ?
C18 C8 C9 C21 108.98(13) . . . . ?
C18 C8 C15 O2 160.93(11) . . . . ?
C18 C8 C15 O3 -22.38(13) . . . . ?
C19 O5 C18 O4 -2.48(18) . . . . ?
C19 O5 C18 C8 177.48(10) . . . . ?
C21 C9 C10 C11 110.96(14) . . . . ?
C23 O7 C22 O6 -0.6(2) . . . . ?
C23 O7 C22 C21 179.43(16) . . . . ?
