#------------------------------------------------------------------------------
#$Date: 2024-10-05 15:34:25 +0300 (Sat, 05 Oct 2024) $
#$Revision: 295072 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160167.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_7160167
loop_
_publ_author_name
'Chouhan, Raju'
'Gogoi, Abhijit'
'Das, Sajal Kumar'
_publ_section_title
;
 Constructing spirooxindoles from non-oxindole precursors: a one-pot
 nitro-reduction/double lactamization approach to
 spiro[indoline-3,3'-quinoline]-2,2'-diones.
;
_journal_issue                   37
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7601
_journal_page_last               7606
_journal_paper_doi               10.1039/d4ob01178c
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C16 H12 N2 O2'
_chemical_formula_sum            'C16 H12 N2 O2'
_chemical_formula_weight         264.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2kcyfb
_audit_creation_date             2024-04-09
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-06-24 deposited with the CCDC.	2024-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                102.192(10)
_cell_angle_beta                 96.254(10)
_cell_angle_gamma                105.998(9)
_cell_formula_units_Z            2
_cell_length_a                   5.713(2)
_cell_length_b                   9.479(4)
_cell_length_c                   12.310(5)
_cell_measurement_reflns_used    2723
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.86
_cell_measurement_theta_min      2.31
_cell_volume                     616.4(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0956
_diffrn_reflns_av_unetI/netI     0.0753
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20817
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.860
_diffrn_reflns_theta_min         1.720
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5821
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1187 before and 0.0880 after correction.
The Ratio of minimum to maximum transmission is 0.7806.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate/ haxane'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.054(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3210
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0534
_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/[\s^2^(Fo^2^)+(0.0585P)^2^+0.1574P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1432
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2172
_reflns_number_total             3210
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01178c2.cif
_cod_data_source_block           ag453_a
_cod_database_code               7160167
_shelx_shelxl_version_number     2019/3
_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   0.981
_shelx_estimated_absorpt_t_min   0.976
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C4(H4), C13(H13), C16(H16), C14(H14), C5(H5), C7(H7),
 C15(H15), C6(H6)
;
_shelx_res_file
;
TITL ag453_a_a.res in P-1
    ag453_a.res
    created by SHELXL-2019/3 at 13:28:49 on 09-Apr-2024
REM Old TITL AG453_a.res in P-1
REM SHELXT solution in P-1: R1 0.123, Rweak 0.006, Alpha 0.031
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Formula found by SHELXT: C16 N2 O2
CELL 0.71073 5.713 9.4793 12.3104 102.192 96.254 105.998
ZERR 2 0.0023 0.0039 0.0051 0.01 0.01 0.009
LATT 1
SFAC C H N O
UNIT 32 24 4 4

L.S. 20
PLAN  5
SIZE 0.2 0.22 0.25
TEMP 23
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2
acta
OMIT 1 3 13
REM <olex2.extras>
REM <HklSrc "%.\\AG453_a.hkl">
REM </olex2.extras>

WGHT    0.058500    0.157400
EXTI    0.053856
FVAR       1.04013
O2    4    0.658717    0.348035    0.474382    11.00000    0.02797    0.01972 =
         0.02293    0.00361    0.00442    0.00577
O1    4    1.117018    0.216248    0.518657    11.00000    0.02771    0.02312 =
         0.03161    0.00757    0.01362    0.00871
N2    3    0.748230    0.549609    0.624836    11.00000    0.02382    0.01724 =
         0.02438    0.00521    0.00302    0.00653
AFIX  43
H2    2    0.672303    0.594378    0.585938    11.00000   -1.20000
AFIX   0
N1    3    0.793987    0.071293    0.582205    11.00000    0.02684    0.01680 =
         0.02532    0.00396    0.00974    0.00639
AFIX  43
H1    2    0.787841   -0.016753    0.543157    11.00000   -1.20000
AFIX   0
C3    1    0.697507    0.251095    0.709386    11.00000    0.01786    0.01799 =
         0.02273    0.00644    0.00473    0.00516
C2    1    0.887449    0.335243    0.649213    11.00000    0.01820    0.01705 =
         0.02352    0.00501    0.00746    0.00459
C1    1    0.951710    0.203553    0.574204    11.00000    0.02124    0.01984 =
         0.02254    0.00532    0.00620    0.00721
C12   1    0.756299    0.410977    0.573155    11.00000    0.01836    0.01792 =
         0.02349    0.00516    0.00791    0.00240
C4    1    0.577698    0.300768    0.793936    11.00000    0.02105    0.01890 =
         0.02515    0.00501    0.00627    0.00502
AFIX  43
H4    2    0.615144    0.403718    0.827655    11.00000   -1.20000
AFIX   0
C10   1    1.043461    0.584044    0.791674    11.00000    0.01759    0.01802 =
         0.02577    0.00622    0.00740    0.00107
C11   1    0.854910    0.625894    0.737521    11.00000    0.02067    0.01583 =
         0.02227    0.00533    0.00667    0.00011
C8    1    0.642301    0.095656    0.661863    11.00000    0.02146    0.02008 =
         0.02312    0.00622    0.00627    0.00705
C9    1    1.116916    0.455619    0.725612    11.00000    0.01836    0.02095 =
         0.02611    0.00428    0.00503    0.00456
AFIX  23
H9A   2    1.194789    0.410469    0.777097    11.00000   -1.20000
H9B   2    1.235466    0.493737    0.679847    11.00000   -1.20000
AFIX   0
C13   1    0.766195    0.736990    0.795510    11.00000    0.02305    0.01853 =
         0.02960    0.00724    0.00668    0.00539
AFIX  43
H13   2    0.639432    0.763503    0.759178    11.00000   -1.20000
AFIX   0
C16   1    1.142251    0.656367    0.903900    11.00000    0.02239    0.02375 =
         0.02903    0.00789    0.00584    0.00386
AFIX  43
H16   2    1.267571    0.629174    0.940723    11.00000   -1.20000
AFIX   0
C14   1    0.868194    0.808109    0.908078    11.00000    0.02740    0.01781 =
         0.02871    0.00347    0.01150    0.00356
AFIX  43
H14   2    0.809177    0.882456    0.947155    11.00000   -1.20000
AFIX   0
C5    1    0.398997    0.193698    0.828078    11.00000    0.02269    0.02520 =
         0.02720    0.00882    0.00928    0.00588
AFIX  43
H5    2    0.318107    0.225663    0.885614    11.00000   -1.20000
AFIX   0
C7    1    0.460897   -0.011560    0.692450    11.00000    0.02637    0.01719 =
         0.02832    0.00610    0.00485    0.00391
AFIX  43
H7    2    0.420849   -0.114366    0.657671    11.00000   -1.20000
AFIX   0
C15   1    1.057205    0.769215    0.962672    11.00000    0.02899    0.02249 =
         0.02407    0.00161    0.00547    0.00155
AFIX  43
H15   2    1.126599    0.817971    1.037810    11.00000   -1.20000
AFIX   0
C6    1    0.341177    0.040818    0.777262    11.00000    0.02369    0.02445 =
         0.02954    0.01033    0.00831    0.00277
AFIX  43
H6    2    0.219553   -0.028448    0.800336    11.00000   -1.20000
AFIX   0
HKLF 4




REM  ag453_a_a.res in P-1
REM wR2 = 0.1432, GooF = S = 1.020, Restrained GooF = 1.020 for all data
REM R1 = 0.0534 for 2172 Fo > 4sig(Fo) and 0.0850 for all 3210 data
REM 182 parameters refined using 0 restraints

END

WGHT      0.0585      0.1573

REM Highest difference peak  0.351,  deepest hole -0.252,  1-sigma level  0.066
Q1    1   1.0638  0.7008  0.9359  11.00000  0.05    0.35
Q2    1   1.0744  0.5196  0.7649  11.00000  0.05    0.34
Q3    1   0.8872 -0.0058  0.5563  11.00000  0.05    0.30
Q4    1   0.4573  0.2479  0.8003  11.00000  0.05    0.28
Q5    1   0.9471  0.2822  0.6190  11.00000  0.05    0.26
;
_shelx_res_checksum              43599
_olex2_date_sample_data_collection 2024-03-26
_olex2_date_sample_submission    2024-03-26
_olex2_submission_original_sample_id AG453
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
O2 O 0.6587(2) 0.34804(13) 0.47438(10) 0.0242(3) Uani 1 1 d . . . . .
O1 O 1.1170(2) 0.21625(14) 0.51866(11) 0.0265(3) Uani 1 1 d . . . . .
N2 N 0.7482(3) 0.54961(16) 0.62484(12) 0.0219(3) Uani 1 1 d . . . . .
H2 H 0.672303 0.594378 0.585938 0.026 Uiso 1 1 calc R U . . .
N1 N 0.7940(3) 0.07129(16) 0.58220(13) 0.0229(4) Uani 1 1 d . . . . .
H1 H 0.787841 -0.016753 0.543157 0.027 Uiso 1 1 calc R U . . .
C3 C 0.6975(3) 0.25109(19) 0.70939(15) 0.0193(4) Uani 1 1 d . . . . .
C2 C 0.8874(3) 0.33524(19) 0.64921(15) 0.0195(4) Uani 1 1 d . . . . .
C1 C 0.9517(3) 0.20355(19) 0.57420(15) 0.0208(4) Uani 1 1 d . . . . .
C12 C 0.7563(3) 0.41098(19) 0.57316(15) 0.0203(4) Uani 1 1 d . . . . .
C4 C 0.5777(3) 0.3008(2) 0.79394(15) 0.0218(4) Uani 1 1 d . . . . .
H4 H 0.615144 0.403718 0.827655 0.026 Uiso 1 1 calc R U . . .
C10 C 1.0435(3) 0.58404(19) 0.79167(15) 0.0210(4) Uani 1 1 d . . . . .
C11 C 0.8549(3) 0.62589(19) 0.73752(15) 0.0204(4) Uani 1 1 d . . . . .
C8 C 0.6423(3) 0.09566(19) 0.66186(15) 0.0211(4) Uani 1 1 d . . . . .
C9 C 1.1169(3) 0.45562(19) 0.72561(15) 0.0223(4) Uani 1 1 d . . . . .
H9A H 1.194789 0.410469 0.777097 0.027 Uiso 1 1 calc R U . . .
H9B H 1.235466 0.493737 0.679847 0.027 Uiso 1 1 calc R U . . .
C13 C 0.7662(3) 0.73699(19) 0.79551(16) 0.0236(4) Uani 1 1 d . . . . .
H13 H 0.639432 0.763503 0.759178 0.028 Uiso 1 1 calc R U . . .
C16 C 1.1423(3) 0.6564(2) 0.90390(16) 0.0254(4) Uani 1 1 d . . . . .
H16 H 1.267571 0.629174 0.940723 0.031 Uiso 1 1 calc R U . . .
C14 C 0.8682(4) 0.8081(2) 0.90808(16) 0.0252(4) Uani 1 1 d . . . . .
H14 H 0.809177 0.882456 0.947155 0.030 Uiso 1 1 calc R U . . .
C5 C 0.3990(3) 0.1937(2) 0.82808(16) 0.0246(4) Uani 1 1 d . . . . .
H5 H 0.318107 0.225663 0.885614 0.030 Uiso 1 1 calc R U . . .
C7 C 0.4609(3) -0.0116(2) 0.69245(16) 0.0245(4) Uani 1 1 d . . . . .
H7 H 0.420849 -0.114366 0.657671 0.029 Uiso 1 1 calc R U . . .
C15 C 1.0572(4) 0.7692(2) 0.96267(16) 0.0271(4) Uani 1 1 d . . . . .
H15 H 1.126599 0.817971 1.037810 0.033 Uiso 1 1 calc R U . . .
C6 C 0.3412(3) 0.0408(2) 0.77726(16) 0.0260(4) Uani 1 1 d . . . . .
H6 H 0.219553 -0.028448 0.800336 0.031 Uiso 1 1 calc R U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0280(7) 0.0197(6) 0.0229(7) 0.0036(5) 0.0044(5) 0.0058(5)
O1 0.0277(7) 0.0231(7) 0.0316(8) 0.0076(6) 0.0136(6) 0.0087(5)
N2 0.0238(8) 0.0172(7) 0.0244(8) 0.0052(6) 0.0030(6) 0.0065(6)
N1 0.0268(8) 0.0168(7) 0.0253(8) 0.0040(6) 0.0097(7) 0.0064(6)
C3 0.0179(8) 0.0180(8) 0.0227(9) 0.0064(7) 0.0047(7) 0.0052(7)
C2 0.0182(8) 0.0171(8) 0.0235(9) 0.0050(7) 0.0075(7) 0.0046(7)
C1 0.0212(9) 0.0198(9) 0.0225(9) 0.0053(7) 0.0062(7) 0.0072(7)
C12 0.0184(9) 0.0179(8) 0.0235(10) 0.0052(7) 0.0079(7) 0.0024(7)
C4 0.0211(9) 0.0189(8) 0.0251(10) 0.0050(7) 0.0063(7) 0.0050(7)
C10 0.0176(9) 0.0180(8) 0.0258(10) 0.0062(7) 0.0074(7) 0.0011(7)
C11 0.0207(9) 0.0158(8) 0.0223(9) 0.0053(7) 0.0067(7) 0.0001(7)
C8 0.0215(9) 0.0201(9) 0.0231(9) 0.0062(7) 0.0063(7) 0.0070(7)
C9 0.0184(9) 0.0209(9) 0.0261(10) 0.0043(7) 0.0050(7) 0.0046(7)
C13 0.0230(9) 0.0185(9) 0.0296(10) 0.0072(7) 0.0067(8) 0.0054(7)
C16 0.0224(9) 0.0238(9) 0.0290(10) 0.0079(8) 0.0058(8) 0.0039(7)
C14 0.0274(10) 0.0178(9) 0.0287(10) 0.0035(7) 0.0115(8) 0.0036(7)
C5 0.0227(9) 0.0252(9) 0.0272(10) 0.0088(8) 0.0093(8) 0.0059(7)
C7 0.0264(10) 0.0172(8) 0.0283(10) 0.0061(7) 0.0049(8) 0.0039(7)
C15 0.0290(10) 0.0225(9) 0.0241(10) 0.0016(7) 0.0055(8) 0.0015(8)
C6 0.0237(10) 0.0244(9) 0.0295(11) 0.0103(8) 0.0083(8) 0.0028(8)
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_
_citation_id
_citation_doi
_citation_year
1 10.1039/d4ob01178c 2024
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
C12 N2 H2 117.7 . . ?
C12 N2 C11 124.64(15) . . ?
C11 N2 H2 117.7 . . ?
C1 N1 H1 124.1 . . ?
C1 N1 C8 111.78(15) . . ?
C8 N1 H1 124.1 . . ?
C4 C3 C2 132.25(16) . . ?
C4 C3 C8 119.55(16) . . ?
C8 C3 C2 108.18(15) . . ?
C3 C2 C1 101.76(13) . . ?
C3 C2 C12 107.97(14) . . ?
C3 C2 C9 115.95(15) . . ?
C12 C2 C1 109.15(14) . . ?
C9 C2 C1 112.59(14) . . ?
C9 C2 C12 109.06(14) . . ?
O1 C1 N1 126.04(16) . . ?
O1 C1 C2 125.97(16) . . ?
N1 C1 C2 107.98(15) . . ?
O2 C12 N2 122.39(16) . . ?
O2 C12 C2 122.76(15) . . ?
N2 C12 C2 114.80(15) . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.81(17) . . ?
C5 C4 H4 120.6 . . ?
C11 C10 C9 117.46(16) . . ?
C16 C10 C11 118.80(17) . . ?
C16 C10 C9 123.64(16) . . ?
C10 C11 N2 119.11(16) . . ?
C13 C11 N2 120.14(16) . . ?
C13 C11 C10 120.70(17) . . ?
C3 C8 N1 109.70(15) . . ?
C7 C8 N1 127.99(16) . . ?
C7 C8 C3 122.31(17) . . ?
C2 C9 H9A 109.7 . . ?
C2 C9 H9B 109.7 . . ?
C10 C9 C2 109.89(15) . . ?
C10 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C11 C13 H13 120.2 . . ?
C14 C13 C11 119.51(17) . . ?
C14 C13 H13 120.2 . . ?
C10 C16 H16 119.4 . . ?
C10 C16 C15 121.12(18) . . ?
C15 C16 H16 119.4 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.53(17) . . ?
C15 C14 H14 119.7 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.69(18) . . ?
C6 C5 H5 119.7 . . ?
C8 C7 H7 121.4 . . ?
C8 C7 C6 117.19(17) . . ?
C6 C7 H7 121.4 . . ?
C16 C15 H15 120.3 . . ?
C14 C15 C16 119.34(18) . . ?
C14 C15 H15 120.3 . . ?
C5 C6 C7 121.37(17) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
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
O2 C12 1.228(2) . ?
O1 C1 1.219(2) . ?
N2 H2 0.8600 . ?
N2 C12 1.349(2) . ?
N2 C11 1.403(2) . ?
N1 H1 0.8600 . ?
N1 C1 1.357(2) . ?
N1 C8 1.402(2) . ?
C3 C2 1.520(2) . ?
C3 C4 1.378(2) . ?
C3 C8 1.397(2) . ?
C2 C1 1.544(2) . ?
C2 C12 1.543(2) . ?
C2 C9 1.536(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.397(2) . ?
C10 C11 1.397(3) . ?
C10 C9 1.502(2) . ?
C10 C16 1.383(3) . ?
C11 C13 1.390(2) . ?
C8 C7 1.384(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C13 H13 0.9300 . ?
C13 C14 1.388(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.393(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.389(3) . ?
C15 H15 0.9300 . ?
C6 H6 0.9300 . ?
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
N2 C11 C13 C14 177.93(16) . . . . ?
N1 C8 C7 C6 177.60(17) . . . . ?
C3 C2 C1 O1 -171.69(17) . . . . ?
C3 C2 C1 N1 7.51(17) . . . . ?
C3 C2 C12 O2 -90.75(19) . . . . ?
C3 C2 C12 N2 86.70(18) . . . . ?
C3 C2 C9 C10 -66.33(19) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C3 C8 C7 C6 -3.0(3) . . . . ?
C2 C3 C4 C5 176.43(18) . . . . ?
C2 C3 C8 N1 4.57(19) . . . . ?
C2 C3 C8 C7 -174.95(16) . . . . ?
C1 N1 C8 C3 0.5(2) . . . . ?
C1 N1 C8 C7 -179.97(18) . . . . ?
C1 C2 C12 O2 19.1(2) . . . . ?
C1 C2 C12 N2 -163.46(15) . . . . ?
C1 C2 C9 C10 177.06(14) . . . . ?
C12 N2 C11 C10 20.9(3) . . . . ?
C12 N2 C11 C13 -156.39(17) . . . . ?
C12 C2 C1 O1 74.4(2) . . . . ?
C12 C2 C1 N1 -106.43(16) . . . . ?
C12 C2 C9 C10 55.74(19) . . . . ?
C4 C3 C2 C1 174.71(19) . . . . ?
C4 C3 C2 C12 -70.5(2) . . . . ?
C4 C3 C2 C9 52.2(3) . . . . ?
C4 C3 C8 N1 -177.03(16) . . . . ?
C4 C3 C8 C7 3.5(3) . . . . ?
C4 C5 C6 C7 1.1(3) . . . . ?
C10 C11 C13 C14 0.7(3) . . . . ?
C10 C16 C15 C14 0.9(3) . . . . ?
C11 N2 C12 O2 179.51(16) . . . . ?
C11 N2 C12 C2 2.0(2) . . . . ?
C11 C10 C9 C2 -36.5(2) . . . . ?
C11 C10 C16 C15 -0.1(3) . . . . ?
C11 C13 C14 C15 0.0(3) . . . . ?
C8 N1 C1 O1 173.87(17) . . . . ?
C8 N1 C1 C2 -5.33(19) . . . . ?
C8 C3 C2 C1 -7.17(18) . . . . ?
C8 C3 C2 C12 107.65(16) . . . . ?
C8 C3 C2 C9 -129.70(16) . . . . ?
C8 C3 C4 C5 -1.5(3) . . . . ?
C8 C7 C6 C5 0.7(3) . . . . ?
C9 C2 C1 O1 -46.9(2) . . . . ?
C9 C2 C1 N1 132.31(16) . . . . ?
C9 C2 C12 O2 142.47(17) . . . . ?
C9 C2 C12 N2 -40.1(2) . . . . ?
C9 C10 C11 N2 -1.4(2) . . . . ?
C9 C10 C11 C13 175.83(16) . . . . ?
C9 C10 C16 C15 -176.39(17) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C16 C10 C11 N2 -177.92(16) . . . . ?
C16 C10 C11 C13 -0.7(3) . . . . ?
C16 C10 C9 C2 139.86(17) . . . . ?