#------------------------------------------------------------------------------
#$Date: 2022-05-05 23:38:39 +0300 (Thu, 05 May 2022) $
#$Revision: 274996 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/45/7244593.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_7244593
loop_
_publ_author_name
'Chen, Zhiyan'
'Huang, Wenbo'
'Yi, Liqi'
'Dong, Xiaohan'
'Sheng, Keyan'
'Li, Minghao'
'Bai, Rongxian'
'Sidorenko, A. Yu.'
'Huang, Jiang'
'Gu, Yanlong'
_publ_section_title
;
 Synthesis of indoles and carbazoles from a lignin model compound
 α-hydroxyacetophenone
;
_journal_issue                   7
_journal_name_full               'Green Chemistry'
_journal_page_first              2919
_journal_page_last               2926
_journal_paper_doi               10.1039/D1GC04892A
_journal_volume                  24
_journal_year                    2022
_chemical_formula_moiety         'C18 H17 N O2'
_chemical_formula_sum            'C18 H17 N O2'
_chemical_formula_weight         279.32
_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             2019-01-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-12-30 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.144(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.7113(6)
_cell_length_b                   9.8511(5)
_cell_length_c                   25.2850(14)
_cell_measurement_reflns_used    5197
_cell_measurement_temperature    293.75(10)
_cell_measurement_theta_max      28.6730
_cell_measurement_theta_min      2.7900
_cell_volume                     2894.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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      293.75(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  58.00   1.00    4.00    --  -11.59  57.00 -60.00   89
  2  ω     47.00  85.00   1.00    4.00    --   11.74  37.00-180.00   38
  3  ω     41.00  96.00   1.00    4.00    --   11.74 178.00-180.00   55
  4  ω    -20.00  22.00   1.00    4.00    --  -11.59 -99.00 120.00   42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0091647000
_diffrn_orient_matrix_UB_12      -0.0699451000
_diffrn_orient_matrix_UB_13      -0.0056358000
_diffrn_orient_matrix_UB_21      -0.0564181000
_diffrn_orient_matrix_UB_22      0.0051390000
_diffrn_orient_matrix_UB_23      0.0073186000
_diffrn_orient_matrix_UB_31      -0.0215023000
_diffrn_orient_matrix_UB_32      0.0162401000
_diffrn_orient_matrix_UB_33      -0.0267077000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            14067
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.021
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.282
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         5094
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0479
_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)+(0.0573P)²+1.3803P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1250
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4201
_reflns_number_total             5094
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1gc04892a2.cif
_cod_data_source_block           indole2
_cod_depositor_comments
'Adding full bibliography for 7244591--7244594.cif.'
_cod_database_code               7244593
_shelx_shelxl_version_number     2017/1
_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 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3B(H3B), C12B(H12B), C2(H2), C7B(H7B), C16B(H16B), C7(H7), C16(H16),
 C12(H12), C13B(H13B), C14B(H14B), C13(H13), C8B(H8B), C15B(H15B), C14(H14),
 C15(H15), C8(H8)
2.b Idealised Me refined as rotating group:
 C10B(H10D,H10E,H10F), C10(H10A,H10B,H10C), C9(H9A,H9B,H9C), C9B(H9BA,H9BB,
 H9BC), C18(H18A,H18B,H18C), C18B(H18D,H18E,H18F)
;
_olex2_date_sample_data_collection 2019-01-25
_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 1.473
_oxdiff_exptl_absorpt_empirical_full_min 0.740
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 0.42823(11) 0.15174(14) 0.69822(5) 0.0367(4) Uani 1 1 d . . . . .
O2B O 0.33524(11) 0.40306(15) 0.55535(5) 0.0375(4) Uani 1 1 d . . . . .
O2 O 0.53859(12) 0.16623(15) 0.63209(6) 0.0426(4) Uani 1 1 d . . . . .
O1B O 0.22600(11) 0.39450(15) 0.62200(6) 0.0412(4) Uani 1 1 d . . . . .
N1B N 0.46335(13) 0.80906(16) 0.73005(6) 0.0298(4) Uani 1 1 d . . . . .
N1 N 0.30387(14) -0.24912(16) 0.52217(6) 0.0309(4) Uani 1 1 d . . . . .
C1 C 0.16001(15) -0.02387(18) 0.60448(7) 0.0251(4) Uani 1 1 d . . . . .
C11B C 0.72444(15) 0.55510(19) 0.63681(7) 0.0239(4) Uani 1 1 d . . . . .
C5B C 0.57871(15) 0.68599(19) 0.68299(7) 0.0241(4) Uani 1 1 d . . . . .
C4B C 0.60489(15) 0.58259(18) 0.64754(7) 0.0231(4) Uani 1 1 d . . . . .
C6B C 0.46279(15) 0.70424(19) 0.69312(7) 0.0251(4) Uani 1 1 d . . . . .
C5 C 0.30305(16) -0.14158(19) 0.55766(7) 0.0261(4) Uani 1 1 d . . . . .
C1B C 0.36983(15) 0.62809(19) 0.66786(7) 0.0253(4) Uani 1 1 d . . . . .
C2B C 0.39964(15) 0.52783(19) 0.63269(7) 0.0255(4) Uani 1 1 d . . . . .
C11 C 0.04139(15) -0.00174(18) 0.61736(7) 0.0253(4) Uani 1 1 d . . . . .
C3B C 0.51430(15) 0.50615(19) 0.62325(7) 0.0248(4) Uani 1 1 d . . . . .
H3B H 0.529566 0.437761 0.599766 0.030 Uiso 1 1 calc R . . . .
C12B C 0.76346(15) 0.42195(19) 0.63192(7) 0.0261(4) Uani 1 1 d . . . . .
H12B H 0.714250 0.349631 0.635973 0.031 Uiso 1 1 calc R . . . .
C4 C 0.39515(16) -0.06470(19) 0.58339(7) 0.0277(4) Uani 1 1 d . . . . .
C2 C 0.25079(15) 0.04993(19) 0.63018(7) 0.0266(4) Uani 1 1 d . . . . .
H2 H 0.235679 0.114304 0.655300 0.032 Uiso 1 1 calc R . . . .
C3 C 0.36541(15) 0.03167(19) 0.61990(7) 0.0267(4) Uani 1 1 d . . . . .
C6 C 0.18707(15) -0.12287(19) 0.56738(7) 0.0257(4) Uani 1 1 d . . . . .
C17B C 0.31029(15) 0.4364(2) 0.60434(8) 0.0292(4) Uani 1 1 d . . . . .
C7B C 0.64639(16) 0.7830(2) 0.71452(7) 0.0291(4) Uani 1 1 d . . . . .
H7B H 0.725438 0.795513 0.716004 0.035 Uiso 1 1 calc R . . . .
C16B C 0.80094(16) 0.6607(2) 0.63071(7) 0.0298(4) Uani 1 1 d . . . . .
H16B H 0.776839 0.750003 0.633691 0.036 Uiso 1 1 calc R . . . .
C7 C 0.11997(17) -0.2228(2) 0.53702(7) 0.0307(4) Uani 1 1 d . . . . .
H7 H 0.040939 -0.235576 0.535444 0.037 Uiso 1 1 calc R . . . .
C17 C 0.45377(16) 0.12191(19) 0.64898(8) 0.0299(4) Uani 1 1 d . . . . .
C16 C 0.02047(16) 0.01476(19) 0.67008(7) 0.0284(4) Uani 1 1 d . . . . .
H16 H 0.081643 0.011287 0.697284 0.034 Uiso 1 1 calc R . . . .
C12 C -0.05307(16) 0.0040(2) 0.57764(7) 0.0305(4) Uani 1 1 d . . . . .
H12 H -0.041652 -0.007362 0.542158 0.037 Uiso 1 1 calc R . . . .
C13B C 0.87457(15) 0.3967(2) 0.62112(7) 0.0288(4) Uani 1 1 d . . . . .
H13B H 0.899244 0.307737 0.617823 0.035 Uiso 1 1 calc R . . . .
C14B C 0.94912(16) 0.5031(2) 0.61519(7) 0.0323(5) Uani 1 1 d . . . . .
H14B H 1.023622 0.485940 0.607827 0.039 Uiso 1 1 calc R . . . .
C13 C -0.16316(16) 0.0262(2) 0.59029(8) 0.0334(5) Uani 1 1 d . . . . .
H13 H -0.224780 0.030354 0.563321 0.040 Uiso 1 1 calc R . . . .
C8B C 0.57398(17) 0.8538(2) 0.74198(7) 0.0326(5) Uani 1 1 d . . . . .
H8B H 0.596557 0.923519 0.765784 0.039 Uiso 1 1 calc R . . . .
C15B C 0.91197(16) 0.6350(2) 0.62031(7) 0.0331(5) Uani 1 1 d . . . . .
H15B H 0.961943 0.706811 0.616736 0.040 Uiso 1 1 calc R . . . .
C14 C -0.18196(17) 0.04239(19) 0.64279(8) 0.0333(5) Uani 1 1 d . . . . .
H14 H -0.255954 0.057281 0.651284 0.040 Uiso 1 1 calc R . . . .
C15 C -0.08982(16) 0.0362(2) 0.68259(8) 0.0324(5) Uani 1 1 d . . . . .
H15 H -0.102039 0.046551 0.718010 0.039 Uiso 1 1 calc R . . . .
C8 C 0.19347(17) -0.2959(2) 0.51086(7) 0.0335(5) Uani 1 1 d . . . . .
H8 H 0.171729 -0.368224 0.488204 0.040 Uiso 1 1 calc R . . . .
C10B C 0.24722(16) 0.6595(2) 0.67572(8) 0.0339(5) Uani 1 1 d . . . . .
H10D H 0.231486 0.623934 0.709410 0.051 Uiso 1 1 calc GR . . . .
H10E H 0.196064 0.618570 0.647582 0.051 Uiso 1 1 calc GR . . . .
H10F H 0.235939 0.756048 0.675164 0.051 Uiso 1 1 calc GR . . . .
C10 C 0.51859(16) -0.0910(2) 0.57432(8) 0.0355(5) Uani 1 1 d . . . . .
H10A H 0.533599 -0.186812 0.576179 0.053 Uiso 1 1 calc GR . . . .
H10B H 0.569556 -0.045215 0.601220 0.053 Uiso 1 1 calc GR . . . .
H10C H 0.530892 -0.057711 0.539794 0.053 Uiso 1 1 calc GR . . . .
C9 C 0.39843(18) -0.3065(2) 0.49692(8) 0.0407(5) Uani 1 1 d . . . . .
H9A H 0.431841 -0.237123 0.477071 0.061 Uiso 1 1 calc GR . . . .
H9B H 0.369821 -0.378445 0.473276 0.061 Uiso 1 1 calc GR . . . .
H9C H 0.455840 -0.341847 0.523815 0.061 Uiso 1 1 calc GR . . . .
C9B C 0.37045(18) 0.8587(2) 0.75834(8) 0.0402(5) Uani 1 1 d . . . . .
H9BA H 0.315987 0.908028 0.734100 0.060 Uiso 1 1 calc GR . . . .
H9BB H 0.401565 0.917501 0.786816 0.060 Uiso 1 1 calc GR . . . .
H9BC H 0.332655 0.783176 0.772732 0.060 Uiso 1 1 calc GR . . . .
C18 C 0.5075(2) 0.2417(2) 0.72930(9) 0.0481(6) Uani 1 1 d . . . . .
H18A H 0.504553 0.329685 0.712889 0.072 Uiso 1 1 calc GR . . . .
H18B H 0.584092 0.205917 0.730984 0.072 Uiso 1 1 calc GR . . . .
H18C H 0.486479 0.249226 0.764691 0.072 Uiso 1 1 calc GR . . . .
C18B C 0.2552(2) 0.3128(2) 0.52472(9) 0.0493(6) Uani 1 1 d . . . . .
H18D H 0.280215 0.296748 0.490526 0.074 Uiso 1 1 calc GR . . . .
H18E H 0.180102 0.353419 0.519968 0.074 Uiso 1 1 calc GR . . . .
H18F H 0.252049 0.228167 0.543333 0.074 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 0.0033 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
C17 O1 C18 115.79(16) . . ?
C17B O2B C18B 116.24(16) . . ?
C6B N1B C9B 129.51(17) . . ?
C8B N1B C6B 108.21(15) . . ?
C8B N1B C9B 121.90(16) . . ?
C5 N1 C9 130.15(17) . . ?
C8 N1 C5 108.01(16) . . ?
C8 N1 C9 121.78(17) . . ?
C2 C1 C11 120.45(16) . . ?
C2 C1 C6 116.83(16) . . ?
C6 C1 C11 122.69(16) . . ?
C12B C11B C4B 120.87(16) . . ?
C16B C11B C4B 121.21(17) . . ?
C16B C11B C12B 117.92(17) . . ?
C4B C5B C6B 119.42(16) . . ?
C4B C5B C7B 133.59(16) . . ?
C7B C5B C6B 106.98(16) . . ?
C5B C4B C11B 122.06(15) . . ?
C3B C4B C11B 120.61(16) . . ?
C3B C4B C5B 117.33(16) . . ?
N1B C6B C5B 106.82(16) . . ?
N1B C6B C1B 129.67(16) . . ?
C1B C6B C5B 123.49(16) . . ?
N1 C5 C4 129.92(17) . . ?
N1 C5 C6 107.10(16) . . ?
C4 C5 C6 122.90(17) . . ?
C6B C1B C10B 121.79(17) . . ?
C2B C1B C6B 115.06(16) . . ?
C2B C1B C10B 123.03(17) . . ?
C1B C2B C3B 122.14(17) . . ?
C1B C2B C17B 120.93(16) . . ?
C3B C2B C17B 116.92(16) . . ?
C16 C11 C1 120.55(16) . . ?
C16 C11 C12 117.65(17) . . ?
C12 C11 C1 121.80(16) . . ?
C4B C3B C2B 122.52(17) . . ?
C4B C3B H3B 118.7 . . ?
C2B C3B H3B 118.7 . . ?
C11B C12B H12B 119.6 . . ?
C13B C12B C11B 120.71(17) . . ?
C13B C12B H12B 119.6 . . ?
C5 C4 C10 121.90(17) . . ?
C3 C4 C5 115.50(16) . . ?
C3 C4 C10 122.50(17) . . ?
C1 C2 H2 118.6 . . ?
C1 C2 C3 122.72(17) . . ?
C3 C2 H2 118.6 . . ?
C4 C3 C2 121.96(17) . . ?
C4 C3 C17 121.14(16) . . ?
C2 C3 C17 116.89(17) . . ?
C1 C6 C5 120.07(16) . . ?
C1 C6 C7 132.81(17) . . ?
C7 C6 C5 106.99(16) . . ?
O2B C17B C2B 111.64(16) . . ?
O1B C17B O2B 122.52(18) . . ?
O1B C17B C2B 125.83(18) . . ?
C5B C7B H7B 126.5 . . ?
C8B C7B C5B 107.01(17) . . ?
C8B C7B H7B 126.5 . . ?
C11B C16B H16B 119.4 . . ?
C15B C16B C11B 121.15(19) . . ?
C15B C16B H16B 119.4 . . ?
C6 C7 H7 126.6 . . ?
C8 C7 C6 106.79(17) . . ?
C8 C7 H7 126.6 . . ?
O1 C17 C3 111.47(16) . . ?
O2 C17 O1 122.21(18) . . ?
O2 C17 C3 126.31(18) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 C11 121.08(17) . . ?
C15 C16 H16 119.5 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.09(18) . . ?
C13 C12 H12 119.5 . . ?
C12B C13B H13B 119.8 . . ?
C12B C13B C14B 120.42(18) . . ?
C14B C13B H13B 119.8 . . ?
C13B C14B H14B 120.3 . . ?
C15B C14B C13B 119.45(17) . . ?
C15B C14B H14B 120.3 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.31(18) . . ?
C14 C13 H13 119.8 . . ?
N1B C8B H8B 124.5 . . ?
C7B C8B N1B 110.98(17) . . ?
C7B C8B H8B 124.5 . . ?
C16B C15B H15B 119.8 . . ?
C14B C15B C16B 120.35(18) . . ?
C14B C15B H15B 119.8 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.42(18) . . ?
C15 C14 H14 120.3 . . ?
C16 C15 H15 119.8 . . ?
C14 C15 C16 120.45(18) . . ?
C14 C15 H15 119.8 . . ?
N1 C8 H8 124.4 . . ?
C7 C8 N1 111.11(18) . . ?
C7 C8 H8 124.4 . . ?
C1B C10B H10D 109.5 . . ?
C1B C10B H10E 109.5 . . ?
C1B C10B H10F 109.5 . . ?
H10D C10B H10E 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1B C9B H9BA 109.5 . . ?
N1B C9B H9BB 109.5 . . ?
N1B C9B H9BC 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O2B C18B H18D 109.5 . . ?
O2B C18B H18E 109.5 . . ?
O2B C18B H18F 109.5 . . ?
H18D C18B H18E 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 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 C17 1.349(2) . ?
O1 C18 1.443(2) . ?
O2B C17B 1.348(2) . ?
O2B C18B 1.446(2) . ?
O2 C17 1.210(2) . ?
O1B C17B 1.206(2) . ?
N1B C6B 1.392(2) . ?
N1B C8B 1.366(2) . ?
N1B C9B 1.459(2) . ?
N1 C5 1.389(2) . ?
N1 C8 1.369(2) . ?
N1 C9 1.459(2) . ?
C1 C11 1.482(2) . ?
C1 C2 1.382(3) . ?
C1 C6 1.416(3) . ?
C11B C4B 1.484(2) . ?
C11B C12B 1.399(3) . ?
C11B C16B 1.394(3) . ?
C5B C4B 1.415(3) . ?
C5B C6B 1.424(2) . ?
C5B C7B 1.421(3) . ?
C4B C3B 1.381(2) . ?
C6B C1B 1.408(3) . ?
C5 C4 1.409(3) . ?
C5 C6 1.422(3) . ?
C1B C2B 1.402(3) . ?
C1B C10B 1.506(2) . ?
C2B C3B 1.409(2) . ?
C2B C17B 1.494(3) . ?
C11 C16 1.395(3) . ?
C11 C12 1.400(3) . ?
C3B H3B 0.9300 . ?
C12B H12B 0.9300 . ?
C12B C13B 1.385(2) . ?
C4 C3 1.398(3) . ?
C4 C10 1.514(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.410(2) . ?
C3 C17 1.487(3) . ?
C6 C7 1.423(3) . ?
C7B H7B 0.9300 . ?
C7B C8B 1.354(3) . ?
C16B H16B 0.9300 . ?
C16B C15B 1.382(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.356(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.384(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(3) . ?
C13B H13B 0.9300 . ?
C13B C14B 1.384(3) . ?
C14B H14B 0.9300 . ?
C14B C15B 1.381(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(3) . ?
C8B H8B 0.9300 . ?
C15B H15B 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.382(3) . ?
C15 H15 0.9300 . ?
C8 H8 0.9300 . ?
C10B H10D 0.9600 . ?
C10B H10E 0.9600 . ?
C10B H10F 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C9B H9BA 0.9600 . ?
C9B H9BB 0.9600 . ?
C9B H9BC 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C18B H18D 0.9600 . ?
C18B H18E 0.9600 . ?
C18B H18F 0.9600 . ?
