# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_20220331
_database_code_depnum_ccdc_archive 'CCDC 2215150'
loop_
_audit_author_name
_audit_author_address
'Dong Li'
; Hubei University of Technology
China
;
_audit_update_record             
;
2022-10-25 deposited with the CCDC.	2023-01-02 downloaded from the CCDC.
;
_audit_creation_date             2022-03-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H12 N2 O'
_chemical_formula_sum            'C12 H12 N2 O'
_chemical_formula_weight         200.24
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O3N2
_chemical_oxdiff_usercomment     r
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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P b c 21'
_space_group_name_Hall           'P 2c -2b'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y+1/2, z'
'x, -y+1/2, z+1/2'

_cell_length_a                   6.03944(15)
_cell_length_b                   12.8249(3)
_cell_length_c                   27.8674(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2158.47(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2150
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.7220
_cell_measurement_theta_min      4.6760
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.904
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            7946
_diffrn_reflns_point_group_measured_fraction_full 0.853
_diffrn_reflns_point_group_measured_fraction_max 0.830
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.904
_diffrn_reflns_theta_min         6.353
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00  -6.00   1.00    1.50    --  -33.50 -77.00 -30.00   65
  2  ω   -101.00 -59.00   1.00    1.50    --  -33.50 -77.00  90.00   42
  3  ω     33.00  59.00   1.00    1.50    --   36.47 -37.00-150.00   26
  4  ω     62.00 110.00   1.00    1.50    --   36.47 178.00-180.00   48
  5  ω    -32.00  -6.00   1.00    1.50    --   36.47 -37.00-150.00   26
  6  ω     60.00  99.00   1.00    1.00    --   36.47 178.00-120.00   39
  7  ω     51.00 108.00   1.00    4.00    --  108.00 -94.00  90.00   57
  8  ω     42.00 129.00   1.00    4.00    --  108.00 -30.00  90.00   87
  9  ω     55.00  91.00   1.00    4.00    --  108.00 -61.00  90.00   36
 10  ω     87.00 178.00   1.00    4.00    --  108.00  30.00  90.00   91
 11  ω    127.00 170.00   1.00    4.00    --  108.00 111.00  90.00   43
 12  ω    -87.00 -61.00   1.00    1.00    --  -33.50 -57.00  90.00   26
 13  ω    -54.00 -21.00   1.00    1.00    --  -33.50 -57.00  90.00   33
 14  ω    -85.00 -41.00   1.00    1.00    --  -33.50 178.00 -30.00   44
 15  ω     76.00 103.00   1.00    1.00    --   36.47 178.00  90.00   27
 16  ω     57.00  95.00   1.00    4.00    --  108.00 178.00-180.00   38
 17  ω     45.00 105.00   1.00    4.00    --  108.00 -94.00-120.00   60
 18  ω     90.00 127.00   1.00    4.00    --  108.00 -61.00-180.00   37
 19  ω    105.00 141.00   1.00    4.00    --  108.00 111.00  30.00   36
 20  ω     10.00  36.00   1.00    1.00    --  -33.50  37.00 -90.00   26
 21  ω     12.00  37.00   1.00    1.00    --  -33.50  37.00 -90.00   25
 22  ω     12.00  37.00   1.00    1.00    --  -33.50  37.00 -90.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0944305000
_diffrn_orient_matrix_UB_12      0.0830483000
_diffrn_orient_matrix_UB_13      -0.0343422000
_diffrn_orient_matrix_UB_21      -0.0503565000
_diffrn_orient_matrix_UB_22      -0.0713307000
_diffrn_orient_matrix_UB_23      -0.0431063000
_diffrn_orient_matrix_UB_31      -0.2315078000
_diffrn_orient_matrix_UB_32      0.0493532000
_diffrn_orient_matrix_UB_33      -0.0046031000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.647
_reflns_Friedel_fraction_full    0.700
_reflns_Friedel_fraction_max     0.668
_reflns_number_gt                2712
_reflns_number_total             3469
_reflns_odcompleteness_completeness 99.91
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 874 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3469
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0638P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1326
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C10'(H10')
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C8'(H8'A,H8'B), C9'(H9'A,H9'B),
 C11'(H11C,H11D)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C2'(H2'), C3'(H3'), C4'(H4'),
 C5'(H5'), C6'(H6')
;
_atom_sites_solution_hydrogens   geom
_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 0.5854(6) 0.5444(3) 0.49718(15) 0.0656(10) Uani 1 1 d . . . . .
N1 N 0.9273(6) 0.4911(3) 0.52381(13) 0.0413(8) Uani 1 1 d . . . . .
N2 N 0.9637(15) 0.3599(8) 0.6406(4) 0.107(3) Uani 1 1 d . . . . .
C1 C 0.9485(9) 0.4016(4) 0.49338(18) 0.0383(9) Uani 1 1 d . . . . .
C2 C 1.1361(7) 0.3899(4) 0.46538(16) 0.0449(10) Uani 1 1 d . . . . .
H2 H 1.2491 0.4391 0.4666 0.054 Uiso 1 1 calc R . . . .
C3 C 1.1537(10) 0.3041(4) 0.43551(18) 0.0570(12) Uani 1 1 d . . . . .
H3 H 1.2778 0.2966 0.4160 0.068 Uiso 1 1 calc R . . . .
C4 C 0.9880(10) 0.2291(9) 0.4343(4) 0.061(3) Uani 1 1 d . . . . .
H4 H 1.0033 0.1703 0.4151 0.074 Uiso 1 1 calc R . . . .
C5 C 0.8016(9) 0.2425(4) 0.46178(19) 0.0560(12) Uani 1 1 d . . . . .
H5 H 0.6879 0.1938 0.4602 0.067 Uiso 1 1 calc R . . . .
C6 C 0.7812(7) 0.3280(3) 0.49177(17) 0.0473(10) Uani 1 1 d . . . . .
H6 H 0.6557 0.3359 0.5108 0.057 Uiso 1 1 calc R . . . .
C7 C 0.7515(7) 0.5576(4) 0.52178(17) 0.0478(10) Uani 1 1 d . . . . .
C8 C 0.7978(8) 0.6496(4) 0.55323(18) 0.0558(12) Uani 1 1 d . . . . .
H8A H 0.6739 0.6635 0.5744 0.067 Uiso 1 1 calc R . . . .
H8B H 0.8271 0.7113 0.5342 0.067 Uiso 1 1 calc R . . . .
C9 C 1.0031(8) 0.6176(8) 0.5819(4) 0.061(2) Uani 1 1 d . . . . .
H9A H 1.1016 0.6766 0.5863 0.073 Uiso 1 1 calc R . . . .
H9B H 0.9616 0.5905 0.6131 0.073 Uiso 1 1 calc R . . . .
C10 C 1.1132(8) 0.5339(4) 0.55195(16) 0.0440(9) Uani 1 1 d . . . . .
H10 H 1.2202 0.5664 0.5301 0.053 Uiso 1 1 calc R . . . .
C11 C 1.2297(8) 0.4509(4) 0.58171(18) 0.0548(11) Uani 1 1 d . . . . .
H11A H 1.2928 0.3994 0.5602 0.066 Uiso 1 1 calc R . . . .
H11B H 1.3507 0.4832 0.5991 0.066 Uiso 1 1 calc R . . . .
C12 C 1.0866(12) 0.3984(4) 0.6156(2) 0.0616(12) Uani 1 1 d . . . . .
O1' O 0.0811(6) 0.2090(3) 0.30916(15) 0.0658(10) Uani 1 1 d . . . . .
N1' N 0.4213(6) 0.2609(3) 0.28161(13) 0.0402(7) Uani 1 1 d . . . . .
N2' N 0.4751(12) 0.3928(8) 0.1628(4) 0.093(3) Uani 1 1 d . . . . .
C1' C 0.4447(9) 0.3488(4) 0.31213(18) 0.0381(9) Uani 1 1 d . . . . .
C2' C 0.6328(8) 0.3610(4) 0.34019(16) 0.0455(10) Uani 1 1 d . . . . .
H2' H 0.7442 0.3110 0.3391 0.055 Uiso 1 1 calc R . . . .
C3' C 0.6561(9) 0.4474(4) 0.37005(17) 0.0559(11) Uani 1 1 d . . . . .
H3' H 0.7841 0.4561 0.3882 0.067 Uiso 1 1 calc R . . . .
C4' C 0.4888(10) 0.5197(9) 0.3725(4) 0.060(3) Uani 1 1 d . . . . .
H4' H 0.5010 0.5758 0.3935 0.072 Uiso 1 1 calc R . . . .
C5' C 0.3013(9) 0.5101(4) 0.3439(2) 0.0566(12) Uani 1 1 d . . . . .
H5' H 0.1911 0.5607 0.3449 0.068 Uiso 1 1 calc R . . . .
C6' C 0.2799(7) 0.4246(3) 0.31396(16) 0.0470(10) Uani 1 1 d . . . . .
H6' H 0.1544 0.4177 0.2949 0.056 Uiso 1 1 calc R . . . .
C7' C 0.2424(7) 0.1949(4) 0.28419(16) 0.0452(10) Uani 1 1 d . . . . .
C8' C 0.2889(8) 0.1018(4) 0.25231(19) 0.0556(11) Uani 1 1 d . . . . .
H8'A H 0.3163 0.0400 0.2715 0.067 Uiso 1 1 calc R . . . .
H8'B H 0.1646 0.0884 0.2311 0.067 Uiso 1 1 calc R . . . .
C9' C 0.4925(9) 0.1311(8) 0.2238(4) 0.061(3) Uani 1 1 d . . . . .
H9'A H 0.4519 0.1566 0.1922 0.073 Uiso 1 1 calc R . . . .
H9'B H 0.5902 0.0716 0.2201 0.073 Uiso 1 1 calc R . . . .
C10' C 0.6048(8) 0.2175(3) 0.25343(17) 0.0443(10) Uani 1 1 d . . . . .
H10' H 0.7111 0.1852 0.2755 0.053 Uiso 1 1 calc R . . . .
C11' C 0.7254(8) 0.3000(4) 0.22377(17) 0.0534(11) Uani 1 1 d . . . . .
H11C H 0.7891 0.3516 0.2452 0.064 Uiso 1 1 calc R . . . .
H11D H 0.8457 0.2672 0.2063 0.064 Uiso 1 1 calc R . . . .
C12' C 0.5808(13) 0.3513(5) 0.1903(2) 0.0638(14) Uani 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 C7 1.227(6) . ?
N1 C1 1.432(6) . ?
N1 C7 1.363(6) . ?
N1 C10 1.476(6) . ?
N2 C12 1.131(11) . ?
C1 C2 1.384(7) . ?
C1 C6 1.383(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.389(11) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(10) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.497(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.531(9) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.513(11) . ?
C10 H10 0.9800 . ?
C10 C11 1.522(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.447(8) . ?
O1' C7' 1.211(6) . ?
N1' C1' 1.420(6) . ?
N1' C7' 1.375(5) . ?
N1' C10' 1.468(6) . ?
N2' C12' 1.130(11) . ?
C1' C2' 1.388(7) . ?
C1' C6' 1.392(6) . ?
C2' H2' 0.9300 . ?
C2' C3' 1.394(6) . ?
C3' H3' 0.9300 . ?
C3' C4' 1.373(10) . ?
C4' H4' 0.9300 . ?
C4' C5' 1.390(11) . ?
C5' H5' 0.9300 . ?
C5' C6' 1.384(7) . ?
C6' H6' 0.9300 . ?
C7' C8' 1.514(7) . ?
C8' H8'A 0.9700 . ?
C8' H8'B 0.9700 . ?
C8' C9' 1.512(10) . ?
C9' H9'A 0.9700 . ?
C9' H9'B 0.9700 . ?
C9' C10' 1.540(10) . ?
C10' H10' 0.9800 . ?
C10' C11' 1.527(6) . ?
C11' H11C 0.9700 . ?
C11' H11D 0.9700 . ?
C11' C12' 1.436(8) . ?

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
C1 N1 C10 123.0(4) . . ?
C7 N1 C1 123.1(4) . . ?
C7 N1 C10 112.4(4) . . ?
C2 C1 N1 119.6(5) . . ?
C6 C1 N1 120.0(5) . . ?
C6 C1 C2 120.3(5) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.3(5) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(6) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.4(9) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.6(6) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.7(5) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
O1 C7 N1 125.0(5) . . ?
O1 C7 C8 126.1(4) . . ?
N1 C7 C8 108.9(4) . . ?
C7 C8 H8A 110.9 . . ?
C7 C8 H8B 110.9 . . ?
C7 C8 C9 104.2(5) . . ?
H8A C8 H8B 108.9 . . ?
C9 C8 H8A 110.9 . . ?
C9 C8 H8B 110.9 . . ?
C8 C9 H9A 110.8 . . ?
C8 C9 H9B 110.8 . . ?
H9A C9 H9B 108.8 . . ?
C10 C9 C8 105.0(7) . . ?
C10 C9 H9A 110.8 . . ?
C10 C9 H9B 110.8 . . ?
N1 C10 C9 102.9(4) . . ?
N1 C10 H10 109.3 . . ?
N1 C10 C11 112.4(4) . . ?
C9 C10 H10 109.3 . . ?
C9 C10 C11 113.5(5) . . ?
C11 C10 H10 109.3 . . ?
C10 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 C10 113.9(4) . . ?
C12 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
N2 C12 C11 175.6(9) . . ?
C1' N1' C10' 123.1(4) . . ?
C7' N1' C1' 122.4(4) . . ?
C7' N1' C10' 112.9(4) . . ?
C2' C1' N1' 120.5(5) . . ?
C2' C1' C6' 119.1(5) . . ?
C6' C1' N1' 120.4(5) . . ?
C1' C2' H2' 119.7 . . ?
C1' C2' C3' 120.6(4) . . ?
C3' C2' H2' 119.7 . . ?
C2' C3' H3' 120.2 . . ?
C4' C3' C2' 119.5(6) . . ?
C4' C3' H3' 120.2 . . ?
C3' C4' H4' 119.7 . . ?
C3' C4' C5' 120.7(9) . . ?
C5' C4' H4' 119.7 . . ?
C4' C5' H5' 120.2 . . ?
C6' C5' C4' 119.5(6) . . ?
C6' C5' H5' 120.2 . . ?
C1' C6' H6' 119.7 . . ?
C5' C6' C1' 120.5(4) . . ?
C5' C6' H6' 119.7 . . ?
O1' C7' N1' 124.8(4) . . ?
O1' C7' C8' 127.2(4) . . ?
N1' C7' C8' 108.0(4) . . ?
C7' C8' H8'A 110.7 . . ?
C7' C8' H8'B 110.7 . . ?
H8'A C8' H8'B 108.8 . . ?
C9' C8' C7' 105.3(5) . . ?
C9' C8' H8'A 110.7 . . ?
C9' C8' H8'B 110.7 . . ?
C8' C9' H9'A 110.8 . . ?
C8' C9' H9'B 110.8 . . ?
C8' C9' C10' 104.8(6) . . ?
H9'A C9' H9'B 108.9 . . ?
C10' C9' H9'A 110.8 . . ?
C10' C9' H9'B 110.8 . . ?
N1' C10' C9' 103.1(4) . . ?
N1' C10' H10' 108.6 . . ?
N1' C10' C11' 112.8(4) . . ?
C9' C10' H10' 108.6 . . ?
C11' C10' C9' 114.7(5) . . ?
C11' C10' H10' 108.6 . . ?
C10' C11' H11C 109.2 . . ?
C10' C11' H11D 109.2 . . ?
H11C C11' H11D 107.9 . . ?
C12' C11' C10' 112.2(4) . . ?
C12' C11' H11C 109.2 . . ?
C12' C11' H11D 109.2 . . ?
N2' C12' C11' 176.9(8) . . ?

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 C7 C8 C9 170.3(6) . . . . ?
N1 C1 C2 C3 -179.0(4) . . . . ?
N1 C1 C6 C5 179.1(4) . . . . ?
N1 C7 C8 C9 -11.2(6) . . . . ?
N1 C10 C11 C12 -59.1(6) . . . . ?
C1 N1 C7 O1 6.4(7) . . . . ?
C1 N1 C7 C8 -172.1(4) . . . . ?
C1 N1 C10 C9 -173.6(6) . . . . ?
C1 N1 C10 C11 -51.1(6) . . . . ?
C1 C2 C3 C4 -1.5(8) . . . . ?
C2 C1 C6 C5 -0.3(7) . . . . ?
C2 C3 C4 C5 2.5(11) . . . . ?
C3 C4 C5 C6 -2.3(11) . . . . ?
C4 C5 C6 C1 1.3(8) . . . . ?
C6 C1 C2 C3 0.5(7) . . . . ?
C7 N1 C1 C2 124.5(5) . . . . ?
C7 N1 C1 C6 -55.0(6) . . . . ?
C7 N1 C10 C9 19.7(6) . . . . ?
C7 N1 C10 C11 142.2(4) . . . . ?
C7 C8 C9 C10 22.7(7) . . . . ?
C8 C9 C10 N1 -25.3(7) . . . . ?
C8 C9 C10 C11 -147.0(5) . . . . ?
C9 C10 C11 C12 57.2(6) . . . . ?
C10 N1 C1 C2 -40.8(6) . . . . ?
C10 N1 C1 C6 139.8(5) . . . . ?
C10 N1 C7 O1 173.1(4) . . . . ?
C10 N1 C7 C8 -5.4(5) . . . . ?
O1' C7' C8' C9' 171.6(6) . . . . ?
N1' C1' C2' C3' 179.8(4) . . . . ?
N1' C1' C6' C5' 179.5(4) . . . . ?
N1' C7' C8' C9' -10.7(6) . . . . ?
N1' C10' C11' C12' -59.6(6) . . . . ?
C1' N1' C7' O1' 6.4(7) . . . . ?
C1' N1' C7' C8' -171.3(4) . . . . ?
C1' N1' C10' C9' -175.4(6) . . . . ?
C1' N1' C10' C11' -51.1(6) . . . . ?
C1' C2' C3' C4' 1.6(9) . . . . ?
C2' C1' C6' C5' -1.1(7) . . . . ?
C2' C3' C4' C5' -3.0(12) . . . . ?
C3' C4' C5' C6' 2.3(12) . . . . ?
C4' C5' C6' C1' -0.3(9) . . . . ?
C6' C1' C2' C3' 0.4(7) . . . . ?
C7' N1' C1' C2' 124.4(5) . . . . ?
C7' N1' C1' C6' -56.2(6) . . . . ?
C7' N1' C10' C9' 18.8(6) . . . . ?
C7' N1' C10' C11' 143.1(4) . . . . ?
C7' C8' C9' C10' 21.5(7) . . . . ?
C8' C9' C10' N1' -24.1(7) . . . . ?
C8' C9' C10' C11' -147.2(5) . . . . ?
C9' C10' C11' C12' 58.1(6) . . . . ?
C10' N1' C1' C2' -40.1(7) . . . . ?
C10' N1' C1' C6' 139.3(5) . . . . ?
C10' N1' C7' O1' 172.4(4) . . . . ?
C10' N1' C7' C8' -5.4(5) . . . . ?

_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 1.315
_oxdiff_exptl_absorpt_empirical_full_min 0.881
