# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_11203
_database_code_depnum_ccdc_archive 'CCDC 1977860'
loop_
_audit_author_name
_audit_author_address
dihydroindoleone
;Shaanxi Normal University
China
;
_audit_update_record             
;
2020-01-15 deposited with the CCDC.	2020-04-09 downloaded from the CCDC.
;
_audit_creation_date             2015-05-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H11 N O3'
_chemical_formula_sum            'C12 H11 N O3'
_chemical_formula_weight         217.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Br C O'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.1648(3)
_cell_length_b                   10.9613(6)
_cell_length_c                   12.0440(7)
_cell_angle_alpha                105.854(5)
_cell_angle_beta                 90.015(6)
_cell_angle_gamma                94.640(6)
_cell_volume                     527.04(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2467
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.9700
_cell_measurement_theta_min      4.1930
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.824
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             228
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.329
_diffrn_reflns_theta_min         3.816
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0356
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    3.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000 -180.0000 58

#__ type_ start__ end____ width___ exp.time_
  2 omega   -2.00   40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -150.0000 42

#__ type_ start__ end____ width___ exp.time_
  3 omega   39.00   64.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega  -17.00   81.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -37.0000  150.0000 98

#__ type_ start__ end____ width___ exp.time_
  5 omega   -3.00   62.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -99.0000  150.0000 65

#__ type_ start__ end____ width___ exp.time_
  6 omega   57.00  113.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397 -125.0000  -60.0000 56

#__ type_ start__ end____ width___ exp.time_
  7 omega   30.00  119.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   37.0000  -30.0000 89

#__ type_ start__ end____ width___ exp.time_
  8 omega    6.00   48.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -57.0000  -30.0000 42

#__ type_ start__ end____ width___ exp.time_
  9 omega  -11.00   62.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -57.0000   30.0000 73

#__ type_ start__ end____ width___ exp.time_
 10 omega   45.00  123.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -91.0000  150.0000 78

#__ type_ start__ end____ width___ exp.time_
 11 omega   75.00  104.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -50.0000  150.0000 29

#__ type_ start__ end____ width___ exp.time_
 12 omega   48.00   92.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -37.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
 13 omega  117.00  166.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   25.0000 -180.0000 49

#__ type_ start__ end____ width___ exp.time_
 14 omega   49.00   87.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000  150.0000 38

#__ type_ start__ end____ width___ exp.time_
 15 omega   78.00  109.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   25.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
 16 omega  124.00  178.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   37.0000   60.0000 54

#__ type_ start__ end____ width___ exp.time_
 17 omega   42.00   82.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -37.0000  -60.0000 40

#__ type_ start__ end____ width___ exp.time_
 18 omega   87.00  115.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   37.0000   60.0000 28

#__ type_ start__ end____ width___ exp.time_
 19 omega   40.00   85.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -37.0000 -150.0000 45

#__ type_ start__ end____ width___ exp.time_
 20 omega   40.00   92.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000 -120.0000 52

#__ type_ start__ end____ width___ exp.time_
 21 omega   51.00  136.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -77.0000    0.0000 85

#__ type_ start__ end____ width___ exp.time_
 22 omega   71.00  116.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794 -111.0000  -60.0000 45

#__ type_ start__ end____ width___ exp.time_
 23 omega   49.00   83.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000   30.0000 34

#__ type_ start__ end____ width___ exp.time_
 24 omega   43.00   70.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -25.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 25 omega   47.00   92.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -37.0000    0.0000 45

#__ type_ start__ end____ width___ exp.time_
 26 omega  140.00  174.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  111.0000   90.0000 34

#__ type_ start__ end____ width___ exp.time_
 27 omega  -30.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000   30.0000 100

#__ type_ start__ end____ width___ exp.time_
 28 omega  -30.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   77.0000  -30.0000 100

#__ type_ start__ end____ width___ exp.time_
 29 omega   25.00  126.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000 -120.0000 101

#__ type_ start__ end____ width___ exp.time_
 30 omega  -13.00   76.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397  -57.0000  -90.0000 89

#__ type_ start__ end____ width___ exp.time_
 31 omega   25.00  126.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000   60.0000 101

#__ type_ start__ end____ width___ exp.time_
 32 omega   34.00  124.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   57.0000  120.0000 90

#__ type_ start__ end____ width___ exp.time_
 33 omega   34.00  124.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   57.0000 -150.0000 90

#__ type_ start__ end____ width___ exp.time_
 34 omega   34.00  124.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   57.0000   30.0000 90

#__ type_ start__ end____ width___ exp.time_
 35 omega   81.00  178.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   77.0000  -60.0000 97

#__ type_ start__ end____ width___ exp.time_
 36 omega   41.00  105.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -50.0000  -60.0000 64

#__ type_ start__ end____ width___ exp.time_
 37 omega   89.00  178.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   50.0000    0.0000 89

#__ type_ start__ end____ width___ exp.time_
 38 omega   85.00  178.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   37.0000   90.0000 93

#__ type_ start__ end____ width___ exp.time_
 39 omega   81.00  178.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   77.0000 -180.0000 97

#__ type_ start__ end____ width___ exp.time_
 40 omega   81.00  178.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   77.0000 -150.0000 97

#__ type_ start__ end____ width___ exp.time_
 41 omega   77.00  178.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   25.0000 -150.0000 101

#__ type_ start__ end____ width___ exp.time_
 42 omega   81.00  178.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   77.0000    0.0000 97

#__ type_ start__ end____ width___ exp.time_
 43 omega   81.00  178.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   77.0000  -90.0000 97

#__ type_ start__ end____ width___ exp.time_
 44 omega   39.00  178.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   12.0000  -30.0000 139

#__ type_ start__ end____ width___ exp.time_
 45 omega   39.00   92.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794  -37.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
 46 omega   81.00  178.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -      111.0794   77.0000   90.0000 97

#__ type_ start__ end____ width___ exp.time_
 47 omega  -72.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -37.0000 -150.0000 98

#__ type_ start__ end____ width___ exp.time_
 48 omega  -69.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000 -180.0000 90

#__ type_ start__ end____ width___ exp.time_
 49 omega   25.00  126.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000  -30.0000 101

#__ type_ start__ end____ width___ exp.time_
 50 omega   25.00   86.00   1.0000    2.4000
omega____ theta____ kappa____ phi______ frames
    -       55.5397   77.0000  150.0000 61
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0032607000
_diffrn_orient_matrix_UB_12      0.0650656000
_diffrn_orient_matrix_UB_13      0.1306508000
_diffrn_orient_matrix_UB_21      0.0227520000
_diffrn_orient_matrix_UB_22      0.1313052000
_diffrn_orient_matrix_UB_23      -0.0242450000
_diffrn_orient_matrix_UB_31      -0.3705023000
_diffrn_orient_matrix_UB_32      -0.0048732000
_diffrn_orient_matrix_UB_33      -0.0057468000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1620
_reflns_number_total             2037
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2037
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0420
_refine_ls_restrained_S_all      1.030
_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)+(0.0575P)²+0.0908P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1181
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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 0.1359(4) -0.08484(10) 0.33274(11) 0.0667(4) Uani 1 1 d . . . . .
O2 O -0.1358(4) -0.02124(12) 0.20262(13) 0.0821(5) Uani 1 1 d . . . . .
O3 O 0.2744(4) 0.56577(10) 0.40029(11) 0.0636(4) Uani 1 1 d . . . . .
N1 N 0.0586(4) 0.36222(12) 0.38348(12) 0.0527(4) Uani 1 1 d . . . . .
H1 H -0.0307 0.3773 0.4497 0.063 Uiso 1 1 calc R . . . .
C1 C 0.2294(4) 0.45199(14) 0.34749(14) 0.0494(4) Uani 1 1 d . . . . .
C2 C 0.3498(4) 0.38842(14) 0.23208(14) 0.0480(4) Uani 1 1 d . . . . .
C3 C 0.2354(4) 0.26134(14) 0.20354(13) 0.0459(4) Uani 1 1 d . . . . .
C4 C 0.0362(4) 0.23653(14) 0.30124(13) 0.0470(4) Uani 1 1 d . . . . .
H4 H -0.1882 0.2131 0.2742 0.056 Uiso 1 1 calc R . . . .
C5 C 0.3074(5) 0.18025(15) 0.09765(14) 0.0544(5) Uani 1 1 d . . . . .
H5 H 0.2314 0.0948 0.0772 0.065 Uiso 1 1 calc R . . . .
C6 C 0.4951(5) 0.23048(18) 0.02377(15) 0.0634(5) Uani 1 1 d . . . . .
H6 H 0.5465 0.1776 -0.0474 0.076 Uiso 1 1 calc R . . . .
C7 C 0.6089(5) 0.35761(18) 0.05292(16) 0.0646(5) Uani 1 1 d . . . . .
H7 H 0.7349 0.3889 0.0014 0.077 Uiso 1 1 calc R . . . .
C8 C 0.5363(5) 0.43857(16) 0.15825(16) 0.0592(5) Uani 1 1 d . . . . .
H8 H 0.6111 0.5242 0.1785 0.071 Uiso 1 1 calc R . . . .
C9 C 0.1486(4) 0.13505(14) 0.35268(13) 0.0459(4) Uani 1 1 d . . . . .
C10 C 0.0341(5) 0.00327(15) 0.28742(15) 0.0527(4) Uani 1 1 d . . . . .
C11 C 0.0226(7) -0.21419(16) 0.2751(2) 0.0798(7) Uani 1 1 d . . . . .
H11A H 0.0803 -0.2335 0.1954 0.120 Uiso 1 1 calc GR . . . .
H11B H -0.2075 -0.2247 0.2803 0.120 Uiso 1 1 calc GR . . . .
H11C H 0.1192 -0.2707 0.3111 0.120 Uiso 1 1 calc GR . . . .
C12 C 0.3246(5) 0.16000(18) 0.44839(16) 0.0597(5) Uani 1 1 d . . . . .
H12A H 0.391(5) 0.2467(19) 0.4909(17) 0.065(6) Uiso 1 1 d . . . . .
H12B H 0.384(5) 0.089(2) 0.4784(19) 0.078(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C10 1.328(2) . ?
O1 C11 1.438(2) . ?
O2 C10 1.198(2) . ?
O3 C1 1.2344(18) . ?
N1 H1 0.8600 . ?
N1 C1 1.335(2) . ?
N1 C4 1.4565(18) . ?
C1 C2 1.482(2) . ?
C2 C3 1.384(2) . ?
C2 C8 1.376(3) . ?
C3 C4 1.512(2) . ?
C3 C5 1.389(2) . ?
C4 H4 0.9800 . ?
C4 C9 1.517(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.384(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.385(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.483(2) . ?
C9 C12 1.317(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.97(2) . ?
C12 H12B 0.99(2) . ?

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
C10 O1 C11 115.76(15) . . ?
C1 N1 H1 122.8 . . ?
C1 N1 C4 114.39(14) . . ?
C4 N1 H1 122.8 . . ?
O3 C1 N1 126.27(16) . . ?
O3 C1 C2 127.14(16) . . ?
N1 C1 C2 106.59(13) . . ?
C3 C2 C1 108.32(15) . . ?
C8 C2 C1 129.72(15) . . ?
C8 C2 C3 121.94(16) . . ?
C2 C3 C4 109.18(14) . . ?
C2 C3 C5 120.10(16) . . ?
C5 C3 C4 130.71(15) . . ?
N1 C4 C3 101.49(12) . . ?
N1 C4 H4 109.0 . . ?
N1 C4 C9 112.66(13) . . ?
C3 C4 H4 109.0 . . ?
C3 C4 C9 115.35(14) . . ?
C9 C4 H4 109.0 . . ?
C3 C5 H5 121.0 . . ?
C6 C5 C3 117.95(16) . . ?
C6 C5 H5 121.0 . . ?
C5 C6 H6 119.2 . . ?
C5 C6 C7 121.64(17) . . ?
C7 C6 H6 119.2 . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.43(18) . . ?
C8 C7 H7 119.8 . . ?
C2 C8 C7 117.94(16) . . ?
C2 C8 H8 121.0 . . ?
C7 C8 H8 121.0 . . ?
C10 C9 C4 113.97(14) . . ?
C12 C9 C4 123.83(15) . . ?
C12 C9 C10 122.17(16) . . ?
O1 C10 C9 113.46(15) . . ?
O2 C10 O1 123.28(15) . . ?
O2 C10 C9 123.25(16) . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 120.9(12) . . ?
C9 C12 H12B 119.5(13) . . ?
H12A C12 H12B 119.6(17) . . ?

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
O3 C1 C2 C3 -178.05(17) . . . . ?
O3 C1 C2 C8 0.4(3) . . . . ?
N1 C1 C2 C3 1.33(19) . . . . ?
N1 C1 C2 C8 179.81(18) . . . . ?
N1 C4 C9 C10 161.18(15) . . . . ?
N1 C4 C9 C12 -17.0(3) . . . . ?
C1 N1 C4 C3 1.18(19) . . . . ?
C1 N1 C4 C9 125.12(17) . . . . ?
C1 C2 C3 C4 -0.61(19) . . . . ?
C1 C2 C3 C5 178.50(15) . . . . ?
C1 C2 C8 C7 -178.42(17) . . . . ?
C2 C3 C4 N1 -0.26(17) . . . . ?
C2 C3 C4 C9 -122.36(15) . . . . ?
C2 C3 C5 C6 0.3(3) . . . . ?
C3 C2 C8 C7 -0.1(3) . . . . ?
C3 C4 C9 C10 -82.93(18) . . . . ?
C3 C4 C9 C12 98.9(2) . . . . ?
C3 C5 C6 C7 -0.2(3) . . . . ?
C4 N1 C1 O3 177.81(16) . . . . ?
C4 N1 C1 C2 -1.6(2) . . . . ?
C4 C3 C5 C6 179.19(18) . . . . ?
C4 C9 C10 O1 179.55(15) . . . . ?
C4 C9 C10 O2 -1.0(3) . . . . ?
C5 C3 C4 N1 -179.25(17) . . . . ?
C5 C3 C4 C9 58.7(2) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C6 C7 C8 C2 0.2(3) . . . . ?
C8 C2 C3 C4 -179.24(16) . . . . ?
C8 C2 C3 C5 -0.1(3) . . . . ?
C11 O1 C10 O2 -1.5(3) . . . . ?
C11 O1 C10 C9 177.92(16) . . . . ?
C12 C9 C10 O1 -2.2(3) . . . . ?
C12 C9 C10 O2 177.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
