# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_3a
_database_code_depnum_ccdc_archive 'CCDC 2221731'
loop_
_audit_author_name
_audit_author_address
'Xuesen Fan'
;Henan Normal University
China
;
_audit_update_record             
;
2022-11-23 deposited with the CCDC.	2023-01-05 downloaded from the CCDC.
;
_audit_creation_date             2021-11-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H20 N2 O2'
_chemical_formula_sum            'C16 H20 N2 O2'
_chemical_formula_weight         272.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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                   7.2189(4)
_cell_length_b                   10.6828(5)
_cell_length_c                   10.8857(7)
_cell_angle_alpha                111.682(5)
_cell_angle_beta                 107.730(5)
_cell_angle_gamma                94.966(4)
_cell_volume                     724.00(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2885
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9890
_cell_measurement_theta_min      4.9990
_shelx_estimated_absorpt_T_max   0.937
_shelx_estimated_absorpt_T_min   0.879
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60607
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4574
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.301
_diffrn_reflns_theta_min         4.571
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -85.00 -60.00   1.00    1.00    --  -35.62 -42.00 -48.00   25
  2  ω    -26.00   0.00   1.00    1.00    --  -35.62  42.00 103.00   26
  3  ω    -12.00  46.00   1.00    1.00    --   35.62 -42.00 -48.00   58
  4  ω     20.00 102.00   1.00    1.00    --   35.62  42.00 103.00   82
  5  ω     40.00 121.00   1.00    1.00    --  107.12 -42.00 -48.00   81
  6  ω     94.00 174.00   1.00    1.00    --  107.12  42.00 103.00   80
  7  ω    -59.00  31.00   1.00    1.00    --  -35.62  77.00-150.00   90
  8  ω   -106.00 -13.00   1.00    1.00    --  -35.62 -19.00  90.00   93
  9  ω      3.00  73.00   1.00    1.00    --   35.62 -99.00 -60.00   70
 10  ω     26.00  73.00   1.00    1.00    --   35.62 -99.00  60.00   47
 11  ω     81.00 106.00   1.00    1.00    --   35.62-178.00-120.00   25
 12  ω    115.00 176.00   1.00    1.00    --  107.12  30.00   0.00   61
 13  ω     67.00 121.00   1.00    1.00    --  107.12 -61.00  30.00   54
 14  ω     43.00 108.00   1.00    1.00    --  107.12 -95.00 -30.00   65
 15  ω     50.00 113.00   1.00    1.00    --  107.12-111.00  90.00   63
 16  ω    100.00 126.00   1.00    1.00    --  107.12 111.00-120.00   26
 17  ω    151.00 176.00   1.00    1.00    --  107.12 111.00  30.00   25
 18  ω    119.00 153.00   1.00    1.00    --  107.12  61.00  30.00   34
 19  ω     40.00 121.00   1.00    1.00    --  107.12 -45.00-180.00   81
 20  ω     94.00 119.00   1.00    1.00    --  107.12  61.00 120.00   25
 21  ω     38.00 110.00   1.00    1.00    --  107.12 -95.00-150.00   72
 22  ω    139.00 171.00   1.00    1.00    --  107.12  61.00 120.00   32
 23  ω    106.00 134.00   1.00    1.00    --  107.12 111.00  30.00   28
 24  ω     76.00 113.00   1.00    1.00    --  107.12-111.00-150.00   37
 25  ω     38.00  92.00   1.00    1.00    --  107.12 -30.00  90.00   54
 26  ω     41.00  67.00   1.00    1.00    --  107.12 -95.00-180.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1401596000
_diffrn_orient_matrix_UB_12      -0.0754001000
_diffrn_orient_matrix_UB_13      0.0696987000
_diffrn_orient_matrix_UB_21      0.0810512000
_diffrn_orient_matrix_UB_22      -0.0392879000
_diffrn_orient_matrix_UB_23      -0.1215637000
_diffrn_orient_matrix_UB_31      0.1632750000
_diffrn_orient_matrix_UB_32      0.1346794000
_diffrn_orient_matrix_UB_33      0.0842021000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2334
_reflns_number_total             2736
_reflns_odcompleteness_completeness 99.96
_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 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    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.117
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2736
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0750
_refine_ls_restrained_S_all      1.079
_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)+(0.1301P)²+0.0769P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1975
_refine_ls_wR_factor_ref         0.2050
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C11(H11A,H11B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.6099(3) 0.21307(19) 0.4811(2) 0.0736(6) Uani 1 1 d . . . . .
H1 H 0.683454 0.290302 0.529130 0.110 Uiso 1 1 calc R U . . .
O2 O 0.7114(2) 0.48114(17) 0.6713(2) 0.0695(5) Uani 1 1 d . . . . .
N1 N 0.3165(2) 0.42223(15) 0.78096(15) 0.0383(4) Uani 1 1 d . . . . .
N2 N 0.4395(2) 0.37933(15) 0.69638(16) 0.0401(4) Uani 1 1 d . . . . .
C1 C 0.4087(4) 0.2238(2) 0.4527(2) 0.0584(6) Uani 1 1 d . . . . .
H1A H 0.323967 0.140843 0.371215 0.070 Uiso 1 1 calc R U . . .
H1B H 0.391230 0.301490 0.427847 0.070 Uiso 1 1 calc R U . . .
C2 C 0.3401(3) 0.24300(19) 0.57641(19) 0.0418(5) Uani 1 1 d . . . . .
C3 C 0.1223(3) 0.2566(2) 0.5433(2) 0.0463(5) Uani 1 1 d . . . . .
H3A H 0.092384 0.317283 0.495570 0.056 Uiso 1 1 calc R U . . .
H3B H 0.029435 0.167424 0.486714 0.056 Uiso 1 1 calc R U . . .
C4 C 0.1220(3) 0.3204(2) 0.6940(2) 0.0417(4) Uani 1 1 d . . . . .
H4 H 0.008393 0.363500 0.698524 0.050 Uiso 1 1 calc R U . . .
C5 C 0.1252(3) 0.2090(2) 0.7478(2) 0.0449(5) Uani 1 1 d . . . . .
C6 C 0.0104(4) 0.1937(2) 0.8251(2) 0.0607(6) Uani 1 1 d . . . . .
H6 H -0.077527 0.251017 0.841268 0.073 Uiso 1 1 calc R U . . .
C7 C 0.0247(5) 0.0955(3) 0.8779(3) 0.0796(9) Uani 1 1 d . . . . .
H7 H -0.053157 0.086116 0.929469 0.095 Uiso 1 1 calc R U . . .
C8 C 0.1558(5) 0.0099(3) 0.8542(3) 0.0783(9) Uani 1 1 d . . . . .
H8 H 0.167634 -0.056059 0.891097 0.094 Uiso 1 1 calc R U . . .
C9 C 0.2687(4) 0.0228(2) 0.7758(3) 0.0628(6) Uani 1 1 d . . . . .
H9 H 0.356066 -0.035156 0.760035 0.075 Uiso 1 1 calc R U . . .
C10 C 0.2539(3) 0.12045(19) 0.7205(2) 0.0462(5) Uani 1 1 d . . . . .
C11 C 0.3710(3) 0.1285(2) 0.6278(2) 0.0483(5) Uani 1 1 d . . . . .
H11A H 0.332246 0.040455 0.545906 0.058 Uiso 1 1 calc R U . . .
H11B H 0.511951 0.143440 0.681084 0.058 Uiso 1 1 calc R U . . .
C12 C 0.5816(3) 0.4853(2) 0.7243(2) 0.0494(5) Uani 1 1 d . . . . .
C13 C 0.5547(3) 0.6104(2) 0.8359(2) 0.0521(5) Uani 1 1 d . . . . .
H13A H 0.584331 0.693041 0.821289 0.062 Uiso 1 1 calc R U . . .
H13B H 0.639536 0.625165 0.930527 0.062 Uiso 1 1 calc R U . . .
C14 C 0.3335(3) 0.57241(19) 0.8132(2) 0.0422(5) Uani 1 1 d . . . . .
C15 C 0.2034(3) 0.6013(2) 0.6910(2) 0.0528(5) Uani 1 1 d . . . . .
H15A H 0.231886 0.553446 0.607278 0.079 Uiso 1 1 calc R U . . .
H15B H 0.231632 0.698898 0.715963 0.079 Uiso 1 1 calc R U . . .
H15C H 0.065180 0.569826 0.672934 0.079 Uiso 1 1 calc R U . . .
C16 C 0.2849(4) 0.6407(2) 0.9456(2) 0.0603(6) Uani 1 1 d . . . . .
H16A H 0.147999 0.603688 0.926438 0.091 Uiso 1 1 calc R U . . .
H16B H 0.305780 0.738584 0.972731 0.091 Uiso 1 1 calc R U . . .
H16C H 0.370074 0.622845 1.021355 0.091 Uiso 1 1 calc R U . . .


_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 H1 0.8200 . ?
O1 C1 1.414(3) . ?
O2 C12 1.237(3) . ?
N1 N2 1.4499(19) . ?
N1 C4 1.488(2) . ?
N1 C14 1.495(2) . ?
N2 C2 1.478(2) . ?
N2 C12 1.335(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.523(2) . ?
C2 C3 1.535(3) . ?
C2 C11 1.529(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.528(3) . ?
C4 H4 0.9800 . ?
C4 C5 1.507(3) . ?
C5 C6 1.387(3) . ?
C5 C10 1.400(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.367(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.386(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(3) . ?
C10 C11 1.520(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.513(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.533(3) . ?
C14 C15 1.530(3) . ?
C14 C16 1.519(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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 O1 H1 109.5 . . ?
N2 N1 C4 103.84(13) . . ?
N2 N1 C14 103.98(13) . . ?
C4 N1 C14 121.28(14) . . ?
N1 N2 C2 110.54(13) . . ?
C12 N2 N1 111.49(15) . . ?
C12 N2 C2 135.10(16) . . ?
O1 C1 H1A 108.8 . . ?
O1 C1 H1B 108.8 . . ?
O1 C1 C2 113.9(2) . . ?
H1A C1 H1B 107.7 . . ?
C2 C1 H1A 108.8 . . ?
C2 C1 H1B 108.8 . . ?
N2 C2 C1 111.67(16) . . ?
N2 C2 C3 99.39(14) . . ?
N2 C2 C11 109.78(16) . . ?
C1 C2 C3 112.68(18) . . ?
C1 C2 C11 112.61(16) . . ?
C11 C2 C3 109.95(15) . . ?
C2 C3 H3A 111.9 . . ?
C2 C3 H3B 111.9 . . ?
H3A C3 H3B 109.6 . . ?
C4 C3 C2 99.60(15) . . ?
C4 C3 H3A 111.9 . . ?
C4 C3 H3B 111.9 . . ?
N1 C4 C3 105.57(14) . . ?
N1 C4 H4 112.1 . . ?
N1 C4 C5 106.63(15) . . ?
C3 C4 H4 112.1 . . ?
C5 C4 C3 107.99(16) . . ?
C5 C4 H4 112.1 . . ?
C6 C5 C4 122.7(2) . . ?
C6 C5 C10 119.5(2) . . ?
C10 C5 C4 117.70(15) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 120.9(2) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.7(2) . . ?
C8 C7 H7 120.2 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.0(2) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 120.9(2) . . ?
C10 C9 H9 119.5 . . ?
C5 C10 C11 120.69(17) . . ?
C9 C10 C5 118.91(18) . . ?
C9 C10 C11 120.37(19) . . ?
C2 C11 H11A 108.8 . . ?
C2 C11 H11B 108.8 . . ?
C10 C11 C2 113.92(16) . . ?
C10 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
O2 C12 N2 126.8(2) . . ?
O2 C12 C13 127.02(19) . . ?
N2 C12 C13 106.19(17) . . ?
C12 C13 H13A 111.1 . . ?
C12 C13 H13B 111.1 . . ?
C12 C13 C14 103.11(16) . . ?
H13A C13 H13B 109.1 . . ?
C14 C13 H13A 111.1 . . ?
C14 C13 H13B 111.1 . . ?
N1 C14 C13 98.27(14) . . ?
N1 C14 C15 114.23(16) . . ?
N1 C14 C16 108.19(15) . . ?
C15 C14 C13 110.50(17) . . ?
C16 C14 C13 114.21(18) . . ?
C16 C14 C15 110.94(17) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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 C1 C2 N2 68.2(2) . . . . ?
O1 C1 C2 C3 179.09(17) . . . . ?
O1 C1 C2 C11 -55.8(2) . . . . ?
O2 C12 C13 C14 156.4(2) . . . . ?
N1 N2 C2 C1 154.02(16) . . . . ?
N1 N2 C2 C3 34.92(17) . . . . ?
N1 N2 C2 C11 -80.36(17) . . . . ?
N1 N2 C12 O2 178.7(2) . . . . ?
N1 N2 C12 C13 -0.2(2) . . . . ?
N1 C4 C5 C6 108.5(2) . . . . ?
N1 C4 C5 C10 -69.9(2) . . . . ?
N2 N1 C4 C3 -19.36(18) . . . . ?
N2 N1 C4 C5 95.33(15) . . . . ?
N2 N1 C14 C13 -38.30(17) . . . . ?
N2 N1 C14 C15 78.67(18) . . . . ?
N2 N1 C14 C16 -157.25(16) . . . . ?
N2 C2 C3 C4 -43.83(17) . . . . ?
N2 C2 C11 C10 71.3(2) . . . . ?
N2 C12 C13 C14 -24.8(2) . . . . ?
C1 C2 C3 C4 -162.17(17) . . . . ?
C1 C2 C11 C10 -163.64(18) . . . . ?
C2 N2 C12 O2 -23.0(4) . . . . ?
C2 N2 C12 C13 158.2(2) . . . . ?
C2 C3 C4 N1 40.05(18) . . . . ?
C2 C3 C4 C5 -73.70(17) . . . . ?
C3 C2 C11 C10 -37.1(2) . . . . ?
C3 C4 C5 C6 -138.4(2) . . . . ?
C3 C4 C5 C10 43.2(2) . . . . ?
C4 N1 N2 C2 -10.24(17) . . . . ?
C4 N1 N2 C12 153.58(16) . . . . ?
C4 N1 C14 C13 -154.39(15) . . . . ?
C4 N1 C14 C15 -37.4(2) . . . . ?
C4 N1 C14 C16 86.7(2) . . . . ?
C4 C5 C6 C7 -176.8(2) . . . . ?
C4 C5 C10 C9 176.15(19) . . . . ?
C4 C5 C10 C11 -5.6(3) . . . . ?
C5 C6 C7 C8 0.1(4) . . . . ?
C5 C10 C11 C2 2.5(3) . . . . ?
C6 C5 C10 C9 -2.3(3) . . . . ?
C6 C5 C10 C11 175.89(18) . . . . ?
C6 C7 C8 C9 -1.0(5) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
C8 C9 C10 C5 1.4(4) . . . . ?
C8 C9 C10 C11 -176.8(2) . . . . ?
C9 C10 C11 C2 -179.4(2) . . . . ?
C10 C5 C6 C7 1.6(4) . . . . ?
C11 C2 C3 C4 71.31(18) . . . . ?
C12 N2 C2 C1 -4.4(3) . . . . ?
C12 N2 C2 C3 -123.5(2) . . . . ?
C12 N2 C2 C11 121.2(2) . . . . ?
C12 C13 C14 N1 38.07(18) . . . . ?
C12 C13 C14 C15 -81.73(19) . . . . ?
C12 C13 C14 C16 152.36(17) . . . . ?
C14 N1 N2 C2 -138.01(15) . . . . ?
C14 N1 N2 C12 25.8(2) . . . . ?
C14 N1 C4 C3 96.79(18) . . . . ?
C14 N1 C4 C5 -148.51(15) . . . . ?

_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 2.290
_oxdiff_exptl_absorpt_empirical_full_min 0.494
####################################################################### 
# 
# 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_5p
_database_code_depnum_ccdc_archive 'CCDC 2221732'
loop_
_audit_author_name
_audit_author_address
'Xuesen Fan'
;Henan Normal University
China
;
_audit_update_record             
;
2022-11-23 deposited with the CCDC.	2023-01-05 downloaded from the CCDC.
;
_audit_creation_date             2022-07-05
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H22 N2 O2'
_chemical_formula_sum            'C17 H22 N2 O2'
_chemical_formula_weight         286.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.6552(2)
_cell_length_b                   14.5864(2)
_cell_length_c                   9.8599(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.578(2)
_cell_angle_gamma                90
_cell_volume                     1483.10(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6157
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.3270
_cell_measurement_theta_min      4.2940
_shelx_estimated_absorpt_T_max   0.936
_shelx_estimated_absorpt_T_min   0.877
_exptl_absorpt_coefficient_mu    0.673
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70251
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10291
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.500
_diffrn_reflns_theta_min         4.287
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -35.00   1.00    1.00    --  -35.62-178.00 120.00   73
  2  ω    -52.00  32.00   1.00    1.00    --  -35.62  57.00 120.00   84
  3  ω   -103.00 -19.00   1.00    1.00    --  -35.62 -57.00 -30.00   84
  4  ω   -108.00 -35.00   1.00    1.00    --  -35.62-178.00  60.00   73
  5  ω    -55.00  34.00   1.00    1.00    --  -35.62  38.00  90.00   89
  6  ω      1.00  75.00   1.00    1.00    --   35.62 -99.00   0.00   74
  7  ω      1.00  75.00   1.00    1.00    --   35.62 -99.00 150.00   74
  8  ω      9.00 103.00   1.00    1.00    --   35.62  77.00 -90.00   94
  9  ω     40.00 125.00   1.00    1.06    --  107.12 -61.00 -90.00   85
 10  ω     45.00  70.00   1.00    1.06    --  107.12 -95.00 -30.00   25
 11  ω     43.00  78.00   1.00    1.06    --  107.12-111.00  90.00   35
 12  ω     84.00 113.00   1.00    1.06    --  107.12-111.00  90.00   29
 13  ω    108.00 176.00   1.00    1.06    --  107.12  45.00 120.00   68
 14  ω    121.00 172.00   1.00    1.06    --  107.12  61.00  60.00   51
 15  ω     37.00 125.00   1.00    1.06    --  107.12 -30.00  30.00   88
 16  ω     41.00  66.00   1.00    1.06    --  107.12 -30.00-180.00   25
 17  ω     41.00 127.00   1.00    1.06    --  107.12 -30.00 -60.00   86
 18  ω     40.00  97.00   1.00    1.06    --  107.12 -45.00 150.00   57
 19  ω     68.00 105.00   1.00    1.06    --  107.12 -95.00-180.00   37
 20  ω     97.00 123.00   1.00    1.06    --  107.12 -30.00-180.00   26
 21  ω     43.00 132.00   1.00    1.06    --  107.12 -77.00  60.00   89
 22  ω     86.00 177.00   1.00    1.06    --  107.12  30.00-150.00   91
 23  ω     82.00 108.00   1.00    1.06    --  107.12 -95.00 -30.00   26
 24  ω    111.00 137.00   1.00    1.06    --  107.12 111.00 -60.00   26
 25  ω     39.00 112.00   1.00    1.06    --  107.12-111.00 -60.00   73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1331355000
_diffrn_orient_matrix_UB_12      0.0371506000
_diffrn_orient_matrix_UB_13      -0.0086257000
_diffrn_orient_matrix_UB_21      0.0077601000
_diffrn_orient_matrix_UB_22      -0.0746692000
_diffrn_orient_matrix_UB_23      -0.1081234000
_diffrn_orient_matrix_UB_31      -0.0673693000
_diffrn_orient_matrix_UB_32      0.0648248000
_diffrn_orient_matrix_UB_33      -0.1195062000
_diffrn_oxdiff_digest_frames     
;
0126ee82d88366bf1c876d0502a831f69000030e09f
;
_diffrn_oxdiff_digest_hkl        
;
0199ce6c8d57df915ad22bf8c3b13df210268a
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2549
_reflns_number_total             2860
_reflns_odcompleteness_completeness 99.93
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.123
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2860
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0613
_refine_ls_restrained_S_all      1.090
_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)+(0.0941P)²+0.4637P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1535
_refine_ls_wR_factor_ref         0.1596
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.84777(16) 0.10954(10) 0.7181(2) 0.0571(5) Uani 1 1 d . . . . .
H1 H 0.8998 0.1358 0.7817 0.086 Uiso 1 1 calc GR . . . .
N1 N 0.78655(12) 0.31389(9) 0.74900(13) 0.0223(3) Uani 1 1 d . . . . .
C1 C 0.7953(2) 0.17282(12) 0.6107(2) 0.0383(4) Uani 1 1 d . . . . .
H1A H 0.7435 0.1398 0.5306 0.046 Uiso 1 1 calc R . . . .
H1B H 0.8659 0.2023 0.5815 0.046 Uiso 1 1 calc R . . . .
O2 O 0.98852(13) 0.25444(11) 0.84954(16) 0.0508(4) Uani 1 1 d . . . . .
N2 N 0.72415(12) 0.40342(8) 0.73282(13) 0.0203(3) Uani 1 1 d . . . . .
C2 C 0.71193(15) 0.24607(10) 0.65330(15) 0.0232(3) Uani 1 1 d . . . . .
H2 H 0.6492 0.2169 0.6972 0.028 Uiso 1 1 calc R . . . .
C3 C 0.63898(16) 0.30556(11) 0.52966(15) 0.0258(4) Uani 1 1 d . . . . .
H3 H 0.6899 0.3156 0.4610 0.031 Uiso 1 1 calc R . . . .
C4 C 0.50512(18) 0.26618(13) 0.46223(18) 0.0364(4) Uani 1 1 d . . . . .
H4A H 0.4748 0.2857 0.3654 0.044 Uiso 1 1 calc R . . . .
H4B H 0.5058 0.1997 0.4660 0.044 Uiso 1 1 calc R . . . .
C5 C 0.42243(17) 0.30592(12) 0.55134(18) 0.0326(4) Uani 1 1 d . . . . .
C6 C 0.29973(19) 0.27777(15) 0.5582(2) 0.0479(5) Uani 1 1 d . . . . .
H6 H 0.2588 0.2288 0.5045 0.057 Uiso 1 1 calc R . . . .
C7 C 0.2398(2) 0.32452(17) 0.6469(3) 0.0552(6) Uani 1 1 d . . . . .
H7 H 0.1588 0.3055 0.6553 0.066 Uiso 1 1 calc R . . . .
C8 C 0.2992(2) 0.39897(15) 0.7229(2) 0.0479(5) Uani 1 1 d . . . . .
H8 H 0.2563 0.4299 0.7804 0.058 Uiso 1 1 calc R . . . .
C9 C 0.42210(17) 0.42930(12) 0.71604(19) 0.0328(4) Uani 1 1 d . . . . .
C10 C 0.48418(15) 0.37982(11) 0.63089(16) 0.0260(4) Uani 1 1 d . . . . .
C11 C 0.61713(15) 0.39557(10) 0.60389(15) 0.0223(3) Uani 1 1 d . . . . .
H11 H 0.6158 0.4486 0.5425 0.027 Uiso 1 1 calc R . . . .
C12 C 0.83596(16) 0.46720(11) 0.73342(17) 0.0289(4) Uani 1 1 d . . . . .
C13 C 0.94042(16) 0.41981(13) 0.84697(18) 0.0331(4) Uani 1 1 d . . . . .
H13A H 1.0266 0.4357 0.8389 0.040 Uiso 1 1 calc R . . . .
H13B H 0.9326 0.4360 0.9399 0.040 Uiso 1 1 calc R . . . .
C14 C 0.91234(16) 0.31948(12) 0.81698(17) 0.0302(4) Uani 1 1 d . . . . .
C15 C 0.4819(2) 0.51246(14) 0.7970(2) 0.0470(5) Uani 1 1 d . . . . .
H15A H 0.5573 0.4946 0.8681 0.070 Uiso 1 1 calc GR . . . .
H15B H 0.4202 0.5405 0.8402 0.070 Uiso 1 1 calc GR . . . .
H15C H 0.5063 0.5554 0.7345 0.070 Uiso 1 1 calc GR . . . .
C16 C 0.8041(2) 0.56335(12) 0.7732(3) 0.0483(5) Uani 1 1 d . . . . .
H16A H 0.7335 0.5875 0.7015 0.072 Uiso 1 1 calc GR . . . .
H16B H 0.8788 0.6019 0.7827 0.072 Uiso 1 1 calc GR . . . .
H16C H 0.7799 0.5614 0.8606 0.072 Uiso 1 1 calc GR . . . .
C17 C 0.8775(2) 0.46745(16) 0.5957(2) 0.0454(5) Uani 1 1 d . . . . .
H17A H 0.8949 0.4058 0.5717 0.068 Uiso 1 1 calc GR . . . .
H17B H 0.9545 0.5039 0.6064 0.068 Uiso 1 1 calc GR . . . .
H17C H 0.8093 0.4929 0.5226 0.068 Uiso 1 1 calc GR . . . .


_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 H1 0.8200 . ?
O1 C1 1.410(2) . ?
N1 N2 1.4559(16) . ?
N1 C2 1.4572(18) . ?
N1 C14 1.342(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.515(2) . ?
O2 C14 1.237(2) . ?
N2 C11 1.4832(19) . ?
N2 C12 1.5104(19) . ?
C2 H2 0.9800 . ?
C2 C3 1.538(2) . ?
C3 H3 0.9800 . ?
C3 C4 1.526(2) . ?
C3 C11 1.549(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.508(3) . ?
C5 C6 1.388(3) . ?
C5 C10 1.396(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.386(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.379(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.400(3) . ?
C9 C10 1.394(2) . ?
C9 C15 1.503(3) . ?
C10 C11 1.523(2) . ?
C11 H11 0.9800 . ?
C12 C13 1.531(2) . ?
C12 C16 1.518(2) . ?
C12 C17 1.531(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.508(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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 O1 H1 109.5 . . ?
N2 N1 C2 112.22(11) . . ?
C14 N1 N2 111.81(12) . . ?
C14 N1 C2 132.72(13) . . ?
O1 C1 H1A 108.8 . . ?
O1 C1 H1B 108.8 . . ?
O1 C1 C2 113.73(16) . . ?
H1A C1 H1B 107.7 . . ?
C2 C1 H1A 108.8 . . ?
C2 C1 H1B 108.8 . . ?
N1 N2 C11 104.84(10) . . ?
N1 N2 C12 102.37(11) . . ?
C11 N2 C12 119.10(12) . . ?
N1 C2 C1 113.31(14) . . ?
N1 C2 H2 109.3 . . ?
N1 C2 C3 102.40(11) . . ?
C1 C2 H2 109.3 . . ?
C1 C2 C3 113.11(13) . . ?
C3 C2 H2 109.3 . . ?
C2 C3 H3 112.0 . . ?
C2 C3 C11 102.11(11) . . ?
C4 C3 C2 111.31(13) . . ?
C4 C3 H3 112.0 . . ?
C4 C3 C11 106.84(14) . . ?
C11 C3 H3 112.0 . . ?
C3 C4 H4A 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
C5 C4 C3 102.74(13) . . ?
C5 C4 H4A 111.2 . . ?
C5 C4 H4B 111.2 . . ?
C6 C5 C4 127.59(18) . . ?
C6 C5 C10 121.17(19) . . ?
C10 C5 C4 111.23(15) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 C5 118.3(2) . . ?
C7 C6 H6 120.8 . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.60(19) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 119.0 . . ?
C7 C8 C9 122.0(2) . . ?
C9 C8 H8 119.0 . . ?
C8 C9 C15 120.38(18) . . ?
C10 C9 C8 117.20(18) . . ?
C10 C9 C15 122.42(16) . . ?
C5 C10 C11 110.23(14) . . ?
C9 C10 C5 120.67(16) . . ?
C9 C10 C11 129.08(15) . . ?
N2 C11 C3 107.21(12) . . ?
N2 C11 C10 114.21(12) . . ?
N2 C11 H11 110.9 . . ?
C3 C11 H11 110.9 . . ?
C10 C11 C3 102.22(12) . . ?
C10 C11 H11 110.9 . . ?
N2 C12 C13 98.76(12) . . ?
N2 C12 C16 110.05(14) . . ?
N2 C12 C17 113.70(14) . . ?
C16 C12 C13 113.39(15) . . ?
C16 C12 C17 111.14(16) . . ?
C17 C12 C13 109.30(15) . . ?
C12 C13 H13A 111.2 . . ?
C12 C13 H13B 111.2 . . ?
H13A C13 H13B 109.1 . . ?
C14 C13 C12 102.88(13) . . ?
C14 C13 H13A 111.2 . . ?
C14 C13 H13B 111.2 . . ?
N1 C14 C13 106.31(14) . . ?
O2 C14 N1 126.21(17) . . ?
O2 C14 C13 127.48(16) . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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 C1 C2 N1 72.72(19) . . . . ?
O1 C1 C2 C3 -171.29(15) . . . . ?
N1 N2 C11 C3 -12.03(14) . . . . ?
N1 N2 C11 C10 100.43(13) . . . . ?
N1 N2 C12 C13 -39.42(14) . . . . ?
N1 N2 C12 C16 -158.35(14) . . . . ?
N1 N2 C12 C17 76.23(17) . . . . ?
N1 C2 C3 C4 -146.34(13) . . . . ?
N1 C2 C3 C11 -32.66(14) . . . . ?
C1 C2 C3 C4 91.36(17) . . . . ?
C1 C2 C3 C11 -154.96(14) . . . . ?
N2 N1 C2 C1 149.96(13) . . . . ?
N2 N1 C2 C3 27.79(15) . . . . ?
N2 N1 C14 O2 177.61(16) . . . . ?
N2 N1 C14 C13 -1.51(17) . . . . ?
N2 C12 C13 C14 38.89(15) . . . . ?
C2 N1 N2 C11 -10.17(15) . . . . ?
C2 N1 N2 C12 -135.14(12) . . . . ?
C2 N1 C14 O2 -24.9(3) . . . . ?
C2 N1 C14 C13 156.01(15) . . . . ?
C2 C3 C4 C5 85.44(16) . . . . ?
C2 C3 C11 N2 28.10(15) . . . . ?
C2 C3 C11 C10 -92.32(13) . . . . ?
C3 C4 C5 C6 -164.33(18) . . . . ?
C3 C4 C5 C10 16.52(18) . . . . ?
C4 C3 C11 N2 145.05(13) . . . . ?
C4 C3 C11 C10 24.63(15) . . . . ?
C4 C5 C6 C7 -179.50(18) . . . . ?
C4 C5 C10 C9 177.07(14) . . . . ?
C4 C5 C10 C11 -1.02(18) . . . . ?
C5 C6 C7 C8 2.1(3) . . . . ?
C5 C10 C11 N2 -130.09(13) . . . . ?
C5 C10 C11 C3 -14.67(16) . . . . ?
C6 C5 C10 C9 -2.1(2) . . . . ?
C6 C5 C10 C11 179.77(16) . . . . ?
C6 C7 C8 C9 -1.2(3) . . . . ?
C7 C8 C9 C10 -1.3(3) . . . . ?
C7 C8 C9 C15 178.11(19) . . . . ?
C8 C9 C10 C5 2.9(2) . . . . ?
C8 C9 C10 C11 -179.36(15) . . . . ?
C9 C10 C11 N2 52.0(2) . . . . ?
C9 C10 C11 C3 167.45(15) . . . . ?
C10 C5 C6 C7 -0.4(3) . . . . ?
C11 N2 C12 C13 -154.38(13) . . . . ?
C11 N2 C12 C16 86.68(17) . . . . ?
C11 N2 C12 C17 -38.7(2) . . . . ?
C11 C3 C4 C5 -25.25(16) . . . . ?
C12 N2 C11 C3 101.61(14) . . . . ?
C12 N2 C11 C10 -145.92(13) . . . . ?
C12 C13 C14 N1 -24.45(17) . . . . ?
C12 C13 C14 O2 156.45(18) . . . . ?
C14 N1 N2 C11 152.16(13) . . . . ?
C14 N1 N2 C12 27.19(15) . . . . ?
C14 N1 C2 C1 -7.5(2) . . . . ?
C14 N1 C2 C3 -129.66(17) . . . . ?
C15 C9 C10 C5 -176.47(16) . . . . ?
C15 C9 C10 C11 1.2(3) . . . . ?
C16 C12 C13 C14 155.29(15) . . . . ?
C17 C12 C13 C14 -80.12(16) . . . . ?

_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 2.002
_oxdiff_exptl_absorpt_empirical_full_min 0.414
