#------------------------------------------------------------------------------
#$Date: 2022-05-05 22:47:33 +0200 (jue 05 de may de 2022) $
#$Revision: 275034 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/13/7061383.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_7061383
loop_
_publ_author_name
'Sarkar, Rumpa'
'Samanta, Surya Kanta'
'Hasija, Avantika'
'Chopra, Deepak'
'Ganguly, Debabani'
'Bera, Mrinal K.'
_publ_section_title
;
 A practical route to arylated dihydroacridine derivatives via nickel
 boride mediated intramolecular reductive cyclization-concomitant
 dehydration
;
_journal_issue                   15
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              7168
_journal_page_last               7176
_journal_paper_doi               10.1039/D1NJ05196B
_journal_volume                  46
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C19 H15 N'
_chemical_formula_sum            'C19 H15 N'
_chemical_formula_weight         257.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-11-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2020-12-07 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.293(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.5986(13)
_cell_length_b                   6.1021(10)
_cell_length_c                   14.110(2)
_cell_measurement_reflns_used    1973
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      28.74
_cell_measurement_theta_min      2.90
_cell_volume                     650.30(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0977
_diffrn_reflns_av_unetI/netI     0.1118
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9748
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.273
_diffrn_reflns_theta_min         2.697
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       needle
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.489
_exptl_crystal_size_mid          0.218
_exptl_crystal_size_min          0.155
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 641 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.5(10)
_refine_ls_extinction_coef       0.040(5)
_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   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         3192
_refine_ls_number_restraints     1057
_refine_ls_restrained_S_all      0.905
_refine_ls_R_factor_all          0.1294
_refine_ls_R_factor_gt           0.0636
_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)+(0.0168P)²+0.1633P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.1074
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                2007
_reflns_number_total             3192
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj05196b2.cif
_cod_data_source_block           mkb_7
_cod_depositor_comments
'Adding full bibliography for 7061383--7061384.cif.'
_cod_database_code               7061383
_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   0.988
_shelx_estimated_absorpt_t_min   0.964
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.006 and sigma
for terminal atoms of 0.008 within 2A
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(N1B)=Sof(C1B)=Sof(C2B)=Sof(H2B)=Sof(C3B)=Sof(H3B)=Sof(C4B)=Sof(H4B)=
 Sof(C5B)=Sof(H5B)=Sof(C6B)=Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(C9B)=Sof(C10B)=
 Sof(H10B)=Sof(C11B)=Sof(C12B)=Sof(H12C)=Sof(H12D)=Sof(C13B)=Sof(H13C)=
 Sof(H13D)=Sof(C14B)=Sof(C15B)=Sof(H15B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=
 Sof(H17B)=Sof(C18B)=Sof(H18B)=Sof(C19B)=Sof(H19B)=1-FVAR(1)
 Sof(N1A)=Sof(C1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(H4A)=
 Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(C9A)=Sof(C10A)=
 Sof(H10A)=Sof(C11A)=Sof(C12A)=Sof(H12A)=Sof(H12B)=Sof(C13A)=Sof(H13A)=
 Sof(H13B)=Sof(C14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=
 Sof(H17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C12A(H12A,H12B), C13A(H13A,H13B), C12B(H12C,H12D), C13B(H13C,H13D)
5.b Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C7A(H7A), C10A(H10A), C15A(H15A),
 C16A(H16A), C17A(H17A), C18A(H18A), C19A(H19A), C2B(H2B), C3B(H3B), C4B(H4B),
 C5B(H5B), C7B(H7B), C10B(H10B), C15B(H15B), C16B(H16B), C17B(H17B), C18B(H18B),
  C19B(H19B)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
N1A N 0.7876(4) 0.2854(6) 0.3804(3) 0.0178(8) Uani 0.714(2) 1 d . U P A 1
C1A C 0.7167(7) 0.3287(11) 0.2884(4) 0.0173(10) Uani 0.714(2) 1 d . U P A 1
C2A C 0.7385(7) 0.1673(9) 0.2186(5) 0.0207(11) Uani 0.714(2) 1 d . U P A 1
H2A H 0.802190 0.036733 0.235793 0.025 Uiso 0.714(2) 1 calc R U P A 1
C3A C 0.6680(8) 0.1996(10) 0.1268(4) 0.0239(13) Uani 0.714(2) 1 d . U P A 1
H3A H 0.684085 0.090837 0.080355 0.029 Uiso 0.714(2) 1 calc R U P A 1
C4A C 0.5720(9) 0.3900(11) 0.0992(5) 0.0248(14) Uani 0.714(2) 1 d . U P A 1
H4A H 0.521502 0.408340 0.035093 0.030 Uiso 0.714(2) 1 calc R U P A 1
C5A C 0.5516(8) 0.5505(10) 0.1664(5) 0.0240(12) Uani 0.714(2) 1 d . U P A 1
H5A H 0.488187 0.680596 0.147890 0.029 Uiso 0.714(2) 1 calc R U P A 1
C6A C 0.6239(8) 0.5231(10) 0.2617(5) 0.0201(11) Uani 0.714(2) 1 d . U P A 1
C7A C 0.6135(6) 0.6833(7) 0.3330(3) 0.0198(10) Uani 0.714(2) 1 d . U P A 1
H7A H 0.554239 0.817782 0.317403 0.024 Uiso 0.714(2) 1 calc R U P A 1
C8A C 0.6870(6) 0.6473(8) 0.4230(4) 0.0180(10) Uani 0.714(2) 1 d . U P A 1
C9A C 0.7686(9) 0.4387(11) 0.4437(5) 0.0153(12) Uani 0.714(2) 1 d . U P A 1
C10A C 0.8292(10) 0.3881(10) 0.5439(5) 0.0180(13) Uani 0.714(2) 1 d . U P A 1
H10A H 0.899916 0.261129 0.557128 0.022 Uiso 0.714(2) 1 calc R U P A 1
C11A C 0.7908(6) 0.5097(8) 0.6172(4) 0.0196(9) Uani 0.714(2) 1 d . U P A 1
C12A C 0.6897(7) 0.7190(8) 0.5986(4) 0.0211(11) Uani 0.714(2) 1 d . U P A 1
H12A H 0.735994 0.828200 0.646966 0.025 Uiso 0.714(2) 1 calc R U P A 1
H12B H 0.564132 0.691689 0.607508 0.025 Uiso 0.714(2) 1 calc R U P A 1
C13A C 0.6977(15) 0.818(2) 0.4998(6) 0.0186(14) Uani 0.714(2) 1 d . U P A 1
H13A H 0.598688 0.922274 0.486178 0.022 Uiso 0.714(2) 1 calc R U P A 1
H13B H 0.809784 0.900065 0.499388 0.022 Uiso 0.714(2) 1 calc R U P A 1
C14A C 0.8321(7) 0.4384(11) 0.7175(4) 0.0193(10) Uani 0.714(2) 1 d . U P A 1
C15A C 0.9271(8) 0.2465(10) 0.7417(4) 0.0206(11) Uani 0.714(2) 1 d . U P A 1
H15A H 0.965790 0.159363 0.692169 0.025 Uiso 0.714(2) 1 calc R U P A 1
C16A C 0.9665(8) 0.1790(11) 0.8348(5) 0.0251(12) Uani 0.714(2) 1 d . U P A 1
H16A H 1.033532 0.049255 0.848508 0.030 Uiso 0.714(2) 1 calc R U P A 1
C17A C 0.9089(8) 0.2995(11) 0.9083(5) 0.0236(13) Uani 0.714(2) 1 d . U P A 1
H17A H 0.934476 0.252560 0.972502 0.028 Uiso 0.714(2) 1 calc R U P A 1
C18A C 0.8130(8) 0.4902(11) 0.8869(4) 0.0235(12) Uani 0.714(2) 1 d . U P A 1
H18A H 0.773022 0.575252 0.936742 0.028 Uiso 0.714(2) 1 calc R U P A 1
C19A C 0.7755(7) 0.5566(9) 0.7925(5) 0.0224(11) Uani 0.714(2) 1 d . U P A 1
H19A H 0.709149 0.687000 0.779025 0.027 Uiso 0.714(2) 1 calc R U P A 1
N1B N 0.8643(11) 0.2763(15) 0.6176(6) 0.0186(15) Uani 0.286(2) 1 d . U P A 2
C1B C 0.8631(19) 0.315(3) 0.7128(10) 0.0209(17) Uani 0.286(2) 1 d . U P A 2
C2B C 0.930(2) 0.184(3) 0.8719(12) 0.026(2) Uani 0.286(2) 1 d . U P A 2
H2B H 0.969071 0.069406 0.914629 0.031 Uiso 0.286(2) 1 calc R U P A 2
C3B C 0.9299(18) 0.150(3) 0.7756(12) 0.024(2) Uani 0.286(2) 1 d . U P A 2
H3B H 0.974721 0.017907 0.752240 0.029 Uiso 0.286(2) 1 calc R U P A 2
C4B C 0.809(2) 0.545(3) 0.8474(15) 0.0243(19) Uani 0.286(2) 1 d . U P A 2
H4B H 0.769556 0.679600 0.871624 0.029 Uiso 0.286(2) 1 calc R U P A 2
C5B C 0.874(2) 0.380(3) 0.9088(14) 0.025(2) Uani 0.286(2) 1 d . U P A 2
H5B H 0.879291 0.400713 0.975838 0.030 Uiso 0.286(2) 1 calc R U P A 2
C6B C 0.804(2) 0.511(3) 0.7479(14) 0.0214(17) Uani 0.286(2) 1 d . U P A 2
C7B C 0.7474(14) 0.6826(19) 0.6829(9) 0.0228(17) Uani 0.286(2) 1 d . U P A 2
H7B H 0.708215 0.819775 0.704499 0.027 Uiso 0.286(2) 1 calc R U P A 2
C8B C 0.7519(17) 0.642(2) 0.5917(11) 0.0195(17) Uani 0.286(2) 1 d . U P A 2
C9B C 0.807(3) 0.437(3) 0.5592(17) 0.0180(19) Uani 0.286(2) 1 d . U P A 2
C10B C 0.796(3) 0.397(3) 0.4610(16) 0.0172(19) Uani 0.286(2) 1 d . U P A 2
H10B H 0.855216 0.269721 0.441397 0.021 Uiso 0.286(2) 1 calc R U P A 2
C11B C 0.7119(15) 0.519(2) 0.3931(9) 0.0182(15) Uani 0.286(2) 1 d . U P A 2
C12B C 0.6299(16) 0.730(2) 0.4196(10) 0.0197(19) Uani 0.286(2) 1 d . U P A 2
H12C H 0.501731 0.708239 0.423338 0.024 Uiso 0.286(2) 1 calc R U P A 2
H12D H 0.643721 0.841641 0.370004 0.024 Uiso 0.286(2) 1 calc R U P A 2
C13B C 0.719(4) 0.811(6) 0.5164(19) 0.020(2) Uani 0.286(2) 1 d . U P A 2
H13C H 0.833859 0.878966 0.506198 0.024 Uiso 0.286(2) 1 calc R U P A 2
H13D H 0.643997 0.927106 0.540050 0.024 Uiso 0.286(2) 1 calc R U P A 2
C14B C 0.680(2) 0.449(3) 0.2879(11) 0.0178(16) Uani 0.286(2) 1 d . U P A 2
C15B C 0.7535(19) 0.260(3) 0.2580(12) 0.0199(18) Uani 0.286(2) 1 d . U P A 2
H15B H 0.826739 0.173883 0.302401 0.024 Uiso 0.286(2) 1 calc R U P A 2
C16B C 0.722(2) 0.191(3) 0.1624(14) 0.0232(19) Uani 0.286(2) 1 d . U P A 2
H16B H 0.778271 0.063105 0.141673 0.028 Uiso 0.286(2) 1 calc R U P A 2
C17B C 0.611(2) 0.309(3) 0.1001(13) 0.022(2) Uani 0.286(2) 1 d . U P A 2
H17B H 0.589985 0.263907 0.035383 0.027 Uiso 0.286(2) 1 calc R U P A 2
C18B C 0.527(2) 0.495(3) 0.1298(13) 0.024(2) Uani 0.286(2) 1 d . U P A 2
H18B H 0.444629 0.572911 0.086777 0.029 Uiso 0.286(2) 1 calc R U P A 2
C19B C 0.5658(19) 0.567(2) 0.2234(14) 0.022(2) Uani 0.286(2) 1 d . U P A 2
H19B H 0.513453 0.698346 0.243437 0.026 Uiso 0.286(2) 1 calc R U P A 2
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'
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
C9A N1A C1A 116.4(5) . . ?
N1A C1A C2A 117.4(6) . . ?
N1A C1A C6A 123.1(6) . . ?
C6A C1A C2A 119.5(5) . . ?
C1A C2A H2A 120.1 . . ?
C3A C2A C1A 119.9(5) . . ?
C3A C2A H2A 120.1 . . ?
C2A C3A H3A 119.3 . . ?
C2A C3A C4A 121.5(6) . . ?
C4A C3A H3A 119.3 . . ?
C3A C4A H4A 120.3 . . ?
C5A C4A C3A 119.3(6) . . ?
C5A C4A H4A 120.3 . . ?
C4A C5A H5A 119.7 . . ?
C4A C5A C6A 120.6(6) . . ?
C6A C5A H5A 119.7 . . ?
C1A C6A C7A 117.3(6) . . ?
C5A C6A C1A 119.1(5) . . ?
C5A C6A C7A 123.6(7) . . ?
C6A C7A H7A 119.7 . . ?
C8A C7A C6A 120.6(5) . . ?
C8A C7A H7A 119.7 . . ?
C7A C8A C9A 117.5(5) . . ?
C7A C8A C13A 123.6(6) . . ?
C9A C8A C13A 118.8(6) . . ?
N1A C9A C8A 124.9(6) . . ?
N1A C9A C10A 117.3(5) . . ?
C8A C9A C10A 117.7(6) . . ?
C9A C10A H10A 118.0 . . ?
C11A C10A C9A 123.9(6) . . ?
C11A C10A H10A 118.0 . . ?
C10A C11A C12A 119.4(5) . . ?
C10A C11A C14A 122.5(5) . . ?
C14A C11A C12A 117.9(5) . . ?
C11A C12A H12A 108.5 . . ?
C11A C12A H12B 108.5 . . ?
C11A C12A C13A 115.1(6) . . ?
H12A C12A H12B 107.5 . . ?
C13A C12A H12A 108.5 . . ?
C13A C12A H12B 108.5 . . ?
C8A C13A C12A 112.6(9) . . ?
C8A C13A H13A 109.1 . . ?
C8A C13A H13B 109.1 . . ?
C12A C13A H13A 109.1 . . ?
C12A C13A H13B 109.1 . . ?
H13A C13A H13B 107.8 . . ?
C15A C14A C11A 122.0(6) . . ?
C19A C14A C11A 121.7(6) . . ?
C19A C14A C15A 116.3(5) . . ?
C14A C15A H15A 118.8 . . ?
C16A C15A C14A 122.4(5) . . ?
C16A C15A H15A 118.8 . . ?
C15A C16A H16A 119.9 . . ?
C15A C16A C17A 120.2(6) . . ?
C17A C16A H16A 119.9 . . ?
C16A C17A H17A 120.5 . . ?
C16A C17A C18A 119.0(6) . . ?
C18A C17A H17A 120.5 . . ?
C17A C18A H18A 120.0 . . ?
C17A C18A C19A 120.0(5) . . ?
C19A C18A H18A 120.0 . . ?
C14A C19A C18A 122.1(5) . . ?
C14A C19A H19A 119.0 . . ?
C18A C19A H19A 119.0 . . ?
C9B N1B C1B 116.6(14) . . ?
N1B C1B C3B 117.5(16) . . ?
N1B C1B C6B 122.3(17) . . ?
C6B C1B C3B 120.2(14) . . ?
C3B C2B H2B 118.9 . . ?
C3B C2B C5B 122.2(17) . . ?
C5B C2B H2B 118.9 . . ?
C1B C3B H3B 120.6 . . ?
C2B C3B C1B 118.7(16) . . ?
C2B C3B H3B 120.6 . . ?
C5B C4B H4B 120.5 . . ?
C5B C4B C6B 119.0(14) . . ?
C6B C4B H4B 120.5 . . ?
C2B C5B H5B 120.2 . . ?
C4B C5B C2B 119.6(16) . . ?
C4B C5B H5B 120.2 . . ?
C1B C6B C4B 120.2(14) . . ?
C1B C6B C7B 119.4(18) . . ?
C4B C6B C7B 120.3(17) . . ?
C6B C7B H7B 121.5 . . ?
C8B C7B C6B 116.9(14) . . ?
C8B C7B H7B 121.5 . . ?
C7B C8B C9B 121.8(17) . . ?
C7B C8B C13B 123.4(18) . . ?
C9B C8B C13B 115(2) . . ?
N1B C9B C8B 123(2) . . ?
N1B C9B C10B 117.6(16) . . ?
C10B C9B C8B 119.5(19) . . ?
C9B C10B H10B 117.1 . . ?
C11B C10B C9B 125.9(19) . . ?
C11B C10B H10B 117.1 . . ?
C10B C11B C12B 119.1(15) . . ?
C10B C11B C14B 123.7(16) . . ?
C12B C11B C14B 117.0(12) . . ?
C11B C12B H12C 109.6 . . ?
C11B C12B H12D 109.6 . . ?
C11B C12B C13B 110.1(16) . . ?
H12C C12B H12D 108.2 . . ?
C13B C12B H12C 109.6 . . ?
C13B C12B H12D 109.6 . . ?
C8B C13B C12B 116(2) . . ?
C8B C13B H13C 108.3 . . ?
C8B C13B H13D 108.3 . . ?
C12B C13B H13C 108.3 . . ?
C12B C13B H13D 108.3 . . ?
H13C C13B H13D 107.4 . . ?
C15B C14B C11B 120.3(16) . . ?
C15B C14B C19B 118.9(14) . . ?
C19B C14B C11B 120.6(16) . . ?
C14B C15B H15B 119.5 . . ?
C14B C15B C16B 121.1(14) . . ?
C16B C15B H15B 119.5 . . ?
C15B C16B H16B 120.4 . . ?
C17B C16B C15B 119.3(15) . . ?
C17B C16B H16B 120.4 . . ?
C16B C17B H17B 119.6 . . ?
C16B C17B C18B 120.8(17) . . ?
C18B C17B H17B 119.6 . . ?
C17B C18B H18B 120.4 . . ?
C17B C18B C19B 119.2(16) . . ?
C19B C18B H18B 120.4 . . ?
C14B C19B C18B 120.6(15) . . ?
C14B C19B H19B 119.7 . . ?
C18B C19B H19B 119.7 . . ?
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
N1A C1A 1.375(6) . ?
N1A C9A 1.312(9) . ?
C1A C2A 1.415(7) . ?
C1A C6A 1.410(7) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.360(8) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.404(7) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.383(8) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.406(8) . ?
C6A C7A 1.411(7) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.348(7) . ?
C8A C9A 1.432(7) . ?
C8A C13A 1.497(13) . ?
C9A C10A 1.471(11) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.330(8) . ?
C11A C12A 1.498(6) . ?
C11A C14A 1.481(7) . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C12A C13A 1.526(12) . ?
C13A H13A 0.9900 . ?
C13A H13B 0.9900 . ?
C14A C15A 1.398(8) . ?
C14A C19A 1.388(7) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.378(8) . ?
C16A H16A 0.9500 . ?
C16A C17A 1.380(8) . ?
C17A H17A 0.9500 . ?
C17A C18A 1.388(8) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.392(8) . ?
C19A H19A 0.9500 . ?
N1B C1B 1.364(17) . ?
N1B C9B 1.33(2) . ?
C1B C3B 1.40(2) . ?
C1B C6B 1.39(2) . ?
C2B H2B 0.9500 . ?
C2B C3B 1.37(2) . ?
C2B C5B 1.39(2) . ?
C3B H3B 0.9500 . ?
C4B H4B 0.9500 . ?
C4B C5B 1.38(2) . ?
C4B C6B 1.42(2) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.424(18) . ?
C7B H7B 0.9500 . ?
C7B C8B 1.314(18) . ?
C8B C9B 1.41(2) . ?
C8B C13B 1.48(3) . ?
C9B C10B 1.40(3) . ?
C10B H10B 0.9500 . ?
C10B C11B 1.323(18) . ?
C11B C12B 1.497(16) . ?
C11B C14B 1.538(18) . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C12B C13B 1.54(3) . ?
C13B H13C 0.9900 . ?
C13B H13D 0.9900 . ?
C14B C15B 1.37(2) . ?
C14B C19B 1.388(19) . ?
C15B H15B 0.9500 . ?
C15B C16B 1.41(2) . ?
C16B H16B 0.9500 . ?
C16B C17B 1.36(2) . ?
C17B H17B 0.9500 . ?
C17B C18B 1.39(2) . ?
C18B H18B 0.9500 . ?
C18B C19B 1.39(2) . ?
C19B H19B 0.9500 . ?
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
N1A C1A C2A C3A 178.7(5) . . . . ?
N1A C1A C6A C5A -178.2(5) . . . . ?
N1A C1A C6A C7A 3.6(7) . . . . ?
N1A C9A C10A C11A -167.6(6) . . . . ?
C1A N1A C9A C8A -2.6(9) . . . . ?
C1A N1A C9A C10A 174.7(6) . . . . ?
C1A C2A C3A C4A -0.5(8) . . . . ?
C1A C6A C7A C8A -1.3(7) . . . . ?
C2A C1A C6A C5A 1.3(7) . . . . ?
C2A C1A C6A C7A -176.9(5) . . . . ?
C2A C3A C4A C5A 1.4(8) . . . . ?
C3A C4A C5A C6A -0.9(9) . . . . ?
C4A C5A C6A C1A -0.4(8) . . . . ?
C4A C5A C6A C7A 177.7(5) . . . . ?
C5A C6A C7A C8A -179.5(5) . . . . ?
C6A C1A C2A C3A -0.9(7) . . . . ?
C6A C7A C8A C9A -2.4(7) . . . . ?
C6A C7A C8A C13A 173.5(7) . . . . ?
C7A C8A C9A N1A 4.7(9) . . . . ?
C7A C8A C9A C10A -172.6(6) . . . . ?
C7A C8A C13A C12A 149.0(6) . . . . ?
C8A C9A C10A C11A 9.9(11) . . . . ?
C9A N1A C1A C2A 178.9(5) . . . . ?
C9A N1A C1A C6A -1.6(7) . . . . ?
C9A C8A C13A C12A -35.2(11) . . . . ?
C9A C10A C11A C12A -4.0(10) . . . . ?
C9A C10A C11A C14A 171.2(6) . . . . ?
C10A C11A C12A C13A -21.6(8) . . . . ?
C10A C11A C14A C15A 5.2(7) . . . . ?
C10A C11A C14A C19A -173.5(6) . . . . ?
C11A C12A C13A C8A 39.9(9) . . . . ?
C11A C14A C15A C16A 179.9(5) . . . . ?
C11A C14A C19A C18A 179.7(5) . . . . ?
C12A C11A C14A C15A -179.4(5) . . . . ?
C12A C11A C14A C19A 1.8(6) . . . . ?
C13A C8A C9A N1A -171.4(8) . . . . ?
C13A C8A C9A C10A 11.3(11) . . . . ?
C14A C11A C12A C13A 162.9(6) . . . . ?
C14A C15A C16A C17A 1.4(9) . . . . ?
C15A C14A C19A C18A 0.9(7) . . . . ?
C15A C16A C17A C18A -0.8(9) . . . . ?
C16A C17A C18A C19A 0.3(8) . . . . ?
C17A C18A C19A C14A -0.4(8) . . . . ?
C19A C14A C15A C16A -1.4(7) . . . . ?
N1B C1B C3B C2B -179.7(13) . . . . ?
N1B C1B C6B C4B -178.5(13) . . . . ?
N1B C1B C6B C7B -2(2) . . . . ?
N1B C9B C10B C11B 166.3(17) . . . . ?
C1B N1B C9B C8B 2(2) . . . . ?
C1B N1B C9B C10B -176.1(17) . . . . ?
C1B C6B C7B C8B 1.0(19) . . . . ?
C3B C1B C6B C4B -1(2) . . . . ?
C3B C1B C6B C7B 175.8(12) . . . . ?
C3B C2B C5B C4B 2(2) . . . . ?
C4B C6B C7B C8B 177.6(14) . . . . ?
C5B C2B C3B C1B -3(2) . . . . ?
C5B C4B C6B C1B 0(2) . . . . ?
C5B C4B C6B C7B -176.7(14) . . . . ?
C6B C1B C3B C2B 2(2) . . . . ?
C6B C4B C5B C2B -1(2) . . . . ?
C6B C7B C8B C9B 1(2) . . . . ?
C6B C7B C8B C13B -172.0(18) . . . . ?
C7B C8B C9B N1B -3(3) . . . . ?
C7B C8B C9B C10B 175.2(17) . . . . ?
C7B C8B C13B C12B -147.5(18) . . . . ?
C8B C9B C10B C11B -12(3) . . . . ?
C9B N1B C1B C3B -177.5(14) . . . . ?
C9B N1B C1B C6B 0.2(19) . . . . ?
C9B C8B C13B C12B 39(3) . . . . ?
C9B C10B C11B C12B 5(3) . . . . ?
C9B C10B C11B C14B -170.2(17) . . . . ?
C10B C11B C12B C13B 22(2) . . . . ?
C10B C11B C14B C15B -6(2) . . . . ?
C10B C11B C14B C19B 169.1(16) . . . . ?
C11B C12B C13B C8B -44(3) . . . . ?
C11B C14B C15B C16B 178.4(12) . . . . ?
C11B C14B C19B C18B -175.4(12) . . . . ?
C12B C11B C14B C15B 178.8(12) . . . . ?
C12B C11B C14B C19B -6.2(17) . . . . ?
C13B C8B C9B N1B 170.8(19) . . . . ?
C13B C8B C9B C10B -11(3) . . . . ?
C14B C11B C12B C13B -162.4(17) . . . . ?
C14B C15B C16B C17B -3(2) . . . . ?
C15B C14B C19B C18B 0(2) . . . . ?
C15B C16B C17B C18B 0(2) . . . . ?
C16B C17B C18B C19B 3(2) . . . . ?
C17B C18B C19B C14B -3(2) . . . . ?
C19B C14B C15B C16B 3(2) . . . . ?
