# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_3a
_database_code_depnum_ccdc_archive 'CCDC 2005938'
loop_
_audit_author_name
_audit_author_address
'Xinying Zhang'
;Henan Normal University
China
;
_audit_update_record             
;
2020-05-26 deposited with the CCDC.	2020-07-14 downloaded from the CCDC.
;
_audit_creation_date             2019-07-11
_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         'C20 H20 N2 O'
_chemical_formula_sum            'C20 H20 N2 O'
_chemical_formula_weight         304.38
_chemical_absolute_configuration ?
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.01650(10)
_cell_length_b                   12.2287(2)
_cell_length_c                   19.4244(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1666.67(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2573
_cell_measurement_temperature    299.04(10)
_cell_measurement_theta_max      71.1250
_cell_measurement_theta_min      4.2430
_shelx_estimated_absorpt_T_max   0.917
_shelx_estimated_absorpt_T_min   0.891
_exptl_absorpt_coefficient_mu    0.591
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68540
_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    1.213
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4511
_diffrn_reflns_point_group_measured_fraction_full 0.923
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.322
_diffrn_reflns_theta_min         4.272
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.04(10)
_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 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -91.00  34.00   1.00    1.00    --  -35.62   7.00-130.00  125
  2  ω    -68.00 -42.00   1.00    1.00    --  -35.62 145.00 119.00   26
  3  ω     70.00 114.00   1.00    3.77    --  107.12   7.00-130.00   44
  4  ω    110.00 161.00   1.00    3.77    --  107.12 126.00 -49.00   51
  5  ω     82.00 155.00   1.00    3.77    --  107.12 146.00-151.00   73
  6  ω     18.00  75.00   1.00    1.00    --   35.62 -99.00 120.00   57
  7  ω     64.00  89.00   1.00    1.00    --   35.62-125.00 -35.00   25
  8  ω    107.00 176.00   1.00    3.77    --  107.12  45.00-150.00   69
  9  ω     70.00 110.00   1.00    3.77    --  107.12 -95.00-150.00   40
 10  ω     51.00  78.00   1.00    3.77    --  107.12-111.00 150.00   27
 11  ω    115.00 166.00   1.00    3.77    --  107.12 111.00   0.00   51
;
_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      -0.0168155000
_diffrn_orient_matrix_UB_12      0.0062683000
_diffrn_orient_matrix_UB_13      -0.0789479000
_diffrn_orient_matrix_UB_21      0.0164092000
_diffrn_orient_matrix_UB_22      -0.1255141000
_diffrn_orient_matrix_UB_23      -0.0042755000
_diffrn_orient_matrix_UB_31      -0.2182906000
_diffrn_orient_matrix_UB_32      -0.0097746000
_diffrn_orient_matrix_UB_33      0.0057238000
_diffrn_oxdiff_digest_frames     
;
01ef6aadf5362319aaca557e1746e841d70003320b6
;
_diffrn_oxdiff_digest_hkl        
;
01a99082f6af42d58507fafe2c339bfb72b083
;
_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         0.571
_reflns_Friedel_fraction_full    0.818
_reflns_Friedel_fraction_max     0.776
_reflns_number_gt                2724
_reflns_number_total             2906
_reflns_odcompleteness_completeness 99.89
_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         0.152
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 947 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2906
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.092
_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)+(0.0462P)²+0.2291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1058
_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
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_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
C1 C 0.5130(3) 0.6538(2) 0.60683(13) 0.0356(5) Uani 1 1 d . . . . .
N1 N 0.7460(3) 0.68144(17) 0.69049(11) 0.0371(4) Uani 1 1 d . . . . .
O1 O 0.9574(3) 0.81536(17) 0.72112(14) 0.0656(6) Uani 1 1 d . . . . .
C2 C 0.4230(4) 0.7292(2) 0.56430(15) 0.0489(7) Uani 1 1 d . . . . .
H2 H 0.3739 0.7933 0.5830 0.059 Uiso 1 1 calc R . . . .
N2 N 0.5418(3) 0.67110(17) 0.67918(11) 0.0379(5) Uani 1 1 d . . . . .
C3 C 0.4058(4) 0.7098(2) 0.49455(17) 0.0557(7) Uani 1 1 d . . . . .
H3 H 0.3452 0.7606 0.4665 0.067 Uiso 1 1 calc R . . . .
C4 C 0.4786(4) 0.6151(2) 0.46663(15) 0.0526(7) Uani 1 1 d . . . . .
H4 H 0.4717 0.6031 0.4194 0.063 Uiso 1 1 calc R . . . .
C5 C 0.5614(4) 0.5383(2) 0.50873(13) 0.0450(6) Uani 1 1 d . . . . .
H5 H 0.6074 0.4738 0.4896 0.054 Uiso 1 1 calc R . . . .
C6 C 0.5783(3) 0.55493(19) 0.57989(12) 0.0358(5) Uani 1 1 d . . . . .
C7 C 0.6572(4) 0.4671(2) 0.62408(12) 0.0368(5) Uani 1 1 d . . . . .
C8 C 0.7605(4) 0.4813(2) 0.68123(12) 0.0386(5) Uani 1 1 d . . . . .
H8 H 0.7827 0.4175 0.7060 0.046 Uiso 1 1 calc R . . . .
C9 C 0.8468(4) 0.5819(2) 0.71257(13) 0.0416(6) Uani 1 1 d . . . . .
C10 C 0.8326(7) 0.5730(3) 0.79107(15) 0.0729(11) Uani 1 1 d . . . . .
H10A H 0.7010 0.5711 0.8044 0.109 Uiso 1 1 calc GR . . . .
H10B H 0.8935 0.6351 0.8119 0.109 Uiso 1 1 calc GR . . . .
H10C H 0.8946 0.5072 0.8061 0.109 Uiso 1 1 calc GR . . . .
C11 C 1.0544(5) 0.5861(3) 0.6894(2) 0.0754(11) Uani 1 1 d . . . . .
H11A H 1.1122 0.5158 0.6963 0.113 Uiso 1 1 calc GR . . . .
H11B H 1.1215 0.6400 0.7159 0.113 Uiso 1 1 calc GR . . . .
H11C H 1.0600 0.6050 0.6415 0.113 Uiso 1 1 calc GR . . . .
C12 C 0.7969(4) 0.7855(2) 0.70529(15) 0.0457(6) Uani 1 1 d . . . . .
C13 C 0.6209(4) 0.8570(2) 0.70054(18) 0.0569(7) Uani 1 1 d . . . . .
H13A H 0.6118 0.8929 0.6561 0.068 Uiso 1 1 calc R . . . .
H13B H 0.6182 0.9116 0.7368 0.068 Uiso 1 1 calc R . . . .
C14 C 0.4648(4) 0.7722(2) 0.70992(16) 0.0503(6) Uani 1 1 d . . . . .
H14A H 0.4367 0.7616 0.7584 0.060 Uiso 1 1 calc R . . . .
H14B H 0.3491 0.7947 0.6865 0.060 Uiso 1 1 calc R . . . .
C15 C 0.6115(4) 0.3519(2) 0.60397(12) 0.0437(6) Uani 1 1 d . . . . .
C16 C 0.4275(5) 0.3234(3) 0.58270(15) 0.0571(8) Uani 1 1 d . . . . .
H16 H 0.3335 0.3769 0.5801 0.069 Uiso 1 1 calc R . . . .
C17 C 0.3844(7) 0.2163(3) 0.56547(18) 0.0754(12) Uani 1 1 d . . . . .
H17 H 0.2615 0.1987 0.5513 0.090 Uiso 1 1 calc R . . . .
C18 C 0.5197(8) 0.1363(3) 0.56895(19) 0.0829(14) Uani 1 1 d . . . . .
H18 H 0.4901 0.0647 0.5568 0.099 Uiso 1 1 calc R . . . .
C19 C 0.7009(7) 0.1629(3) 0.59065(19) 0.0751(11) Uani 1 1 d . . . . .
H19 H 0.7931 0.1086 0.5939 0.090 Uiso 1 1 calc R . . . .
C20 C 0.7474(6) 0.2699(2) 0.60771(16) 0.0583(8) Uani 1 1 d . . . . .
H20 H 0.8707 0.2866 0.6218 0.070 Uiso 1 1 calc R . . . .


_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
C1 C2 1.389(4) . ?
C1 N2 1.435(3) . ?
C1 C6 1.395(3) . ?
N1 N2 1.455(3) . ?
N1 C9 1.471(3) . ?
N1 C12 1.352(3) . ?
O1 C12 1.223(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.381(4) . ?
N2 C14 1.476(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.374(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.402(3) . ?
C6 C7 1.482(3) . ?
C7 C8 1.337(3) . ?
C7 C15 1.497(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.501(3) . ?
C9 C10 1.532(4) . ?
C9 C11 1.525(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.516(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.519(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.399(5) . ?
C15 C20 1.386(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.365(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.378(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.388(5) . ?
C20 H20 0.9300 . ?

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
C2 C1 N2 123.3(2) . . ?
C2 C1 C6 120.1(2) . . ?
C6 C1 N2 116.6(2) . . ?
N2 N1 C9 116.45(19) . . ?
C12 N1 N2 112.0(2) . . ?
C12 N1 C9 126.1(2) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 N2 N1 107.42(18) . . ?
C1 N2 C14 117.9(2) . . ?
N1 N2 C14 103.11(19) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.6(3) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 117.9(2) . . ?
C1 C6 C7 122.3(2) . . ?
C5 C6 C7 119.8(2) . . ?
C6 C7 C15 116.8(2) . . ?
C8 C7 C6 126.1(2) . . ?
C8 C7 C15 117.1(2) . . ?
C7 C8 H8 114.3 . . ?
C7 C8 C9 131.5(2) . . ?
C9 C8 H8 114.3 . . ?
N1 C9 C8 111.46(19) . . ?
N1 C9 C10 108.5(2) . . ?
N1 C9 C11 110.2(2) . . ?
C8 C9 C10 108.6(2) . . ?
C8 C9 C11 107.0(2) . . ?
C11 C9 C10 111.0(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C13 108.3(2) . . ?
O1 C12 N1 125.3(3) . . ?
O1 C12 C13 126.4(3) . . ?
C12 C13 H13A 111.6 . . ?
C12 C13 H13B 111.6 . . ?
C12 C13 C14 100.8(2) . . ?
H13A C13 H13B 109.4 . . ?
C14 C13 H13A 111.6 . . ?
C14 C13 H13B 111.6 . . ?
N2 C14 C13 105.0(2) . . ?
N2 C14 H14A 110.7 . . ?
N2 C14 H14B 110.7 . . ?
C13 C14 H14A 110.7 . . ?
C13 C14 H14B 110.7 . . ?
H14A C14 H14B 108.8 . . ?
C16 C15 C7 120.6(3) . . ?
C20 C15 C7 121.3(3) . . ?
C20 C15 C16 118.1(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.5(4) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.9(4) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 120.4 . . ?
C17 C18 C19 119.2(3) . . ?
C19 C18 H18 120.4 . . ?
C18 C19 H19 119.6 . . ?
C18 C19 C20 120.9(4) . . ?
C20 C19 H19 119.6 . . ?
C15 C20 C19 120.5(4) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?

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
C1 C2 C3 C4 -0.1(5) . . . . ?
C1 N2 C14 C13 -87.5(3) . . . . ?
C1 C6 C7 C8 -34.9(4) . . . . ?
C1 C6 C7 C15 143.0(2) . . . . ?
N1 N2 C14 C13 30.6(3) . . . . ?
N1 C12 C13 C14 21.9(3) . . . . ?
O1 C12 C13 C14 -156.8(3) . . . . ?
C2 C1 N2 N1 -113.3(3) . . . . ?
C2 C1 N2 C14 2.5(3) . . . . ?
C2 C1 C6 C5 4.2(4) . . . . ?
C2 C1 C6 C7 -173.6(2) . . . . ?
C2 C3 C4 C5 2.5(4) . . . . ?
N2 C1 C2 C3 177.5(3) . . . . ?
N2 C1 C6 C5 -176.6(2) . . . . ?
N2 C1 C6 C7 5.6(3) . . . . ?
N2 N1 C9 C8 33.7(3) . . . . ?
N2 N1 C9 C10 -85.9(3) . . . . ?
N2 N1 C9 C11 152.4(2) . . . . ?
N2 N1 C12 O1 175.2(3) . . . . ?
N2 N1 C12 C13 -3.4(3) . . . . ?
C3 C4 C5 C6 -1.5(4) . . . . ?
C4 C5 C6 C1 -1.8(4) . . . . ?
C4 C5 C6 C7 176.1(2) . . . . ?
C5 C6 C7 C8 147.3(3) . . . . ?
C5 C6 C7 C15 -34.8(3) . . . . ?
C6 C1 C2 C3 -3.3(4) . . . . ?
C6 C1 N2 N1 67.6(2) . . . . ?
C6 C1 N2 C14 -176.7(2) . . . . ?
C6 C7 C8 C9 -8.7(5) . . . . ?
C6 C7 C15 C16 -42.7(3) . . . . ?
C6 C7 C15 C20 139.2(3) . . . . ?
C7 C8 C9 N1 24.0(4) . . . . ?
C7 C8 C9 C10 143.5(3) . . . . ?
C7 C8 C9 C11 -96.6(3) . . . . ?
C7 C15 C16 C17 -178.7(3) . . . . ?
C7 C15 C20 C19 178.2(3) . . . . ?
C8 C7 C15 C16 135.4(3) . . . . ?
C8 C7 C15 C20 -42.7(4) . . . . ?
C9 N1 N2 C1 -96.6(2) . . . . ?
C9 N1 N2 C14 138.2(2) . . . . ?
C9 N1 C12 O1 22.6(5) . . . . ?
C9 N1 C12 C13 -156.1(3) . . . . ?
C12 N1 N2 C1 107.9(2) . . . . ?
C12 N1 N2 C14 -17.3(3) . . . . ?
C12 N1 C9 C8 -174.7(2) . . . . ?
C12 N1 C9 C10 65.7(3) . . . . ?
C12 N1 C9 C11 -56.0(4) . . . . ?
C12 C13 C14 N2 -31.9(3) . . . . ?
C15 C7 C8 C9 173.4(3) . . . . ?
C15 C16 C17 C18 0.1(5) . . . . ?
C16 C15 C20 C19 0.1(4) . . . . ?
C16 C17 C18 C19 0.7(6) . . . . ?
C17 C18 C19 C20 -1.1(6) . . . . ?
C18 C19 C20 C15 0.7(5) . . . . ?
C20 C15 C16 C17 -0.5(4) . . . . ?


_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 1.311
_oxdiff_exptl_absorpt_empirical_full_min 0.753
####################################################################### 
# 
# 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_5a
_database_code_depnum_ccdc_archive 'CCDC 2005952'
loop_
_audit_author_name
_audit_author_address
'Xinying Zhang'
;Henan Normal University
China
;
_audit_update_record             
;
2020-05-26 deposited with the CCDC.	2020-07-14 downloaded from the CCDC.
;
_audit_creation_date             2020-05-20
_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         'C22 H22 N2 O'
_chemical_formula_sum            'C22 H22 N2 O'
_chemical_formula_weight         330.41
_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 0.0033 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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.6394(5)
_cell_length_b                   22.9296(11)
_cell_length_c                   10.4410(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.958(6)
_cell_angle_gamma                90
_cell_volume                     1766.96(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4148
_cell_measurement_temperature    283(2)
_cell_measurement_theta_max      28.5490
_cell_measurement_theta_min      4.0360
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75947
_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    1.242
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13029
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.994
_diffrn_reflns_theta_min         3.283
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      283(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 0.889
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     22.00  48.00   1.00    8.09    --   16.13-121.00   3.00   26
  2  ω     27.00  52.00   1.00    8.09    --   16.13-152.00-155.00   25
  3  ω    -68.00 -43.00   1.00    8.09    --  -16.83 121.00  86.00   25
  4  ω     -1.00  82.00   1.00    8.09    --   16.13  57.00  30.00   83
  5  ω      4.00  32.00   1.00    8.09    --   16.13  57.00 120.00   28
  6  ω     35.00  66.00   1.00    8.09    --   16.13 178.00   0.00   31
  7  ω    -42.00  31.00   1.00    8.09    --   16.13 -57.00  90.00   73
  8  ω    -14.00  13.00   1.00    8.09    --   16.13 -99.00-180.00   27
  9  ω     35.00  65.00   1.00    8.09    --   16.13 178.00 -30.00   30
;
_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      -0.0304108000
_diffrn_orient_matrix_UB_12      -0.0216543000
_diffrn_orient_matrix_UB_13      -0.0492058000
_diffrn_orient_matrix_UB_21      0.0162978000
_diffrn_orient_matrix_UB_22      -0.0218380000
_diffrn_orient_matrix_UB_23      0.0498165000
_diffrn_orient_matrix_UB_31      -0.0896839000
_diffrn_orient_matrix_UB_32      0.0033797000
_diffrn_orient_matrix_UB_33      0.0063269000
_diffrn_oxdiff_digest_frames     
;
01410690b444ab35a9581f0086f7344c6000028b776
;
_diffrn_oxdiff_digest_hkl        
;
0163e57aad4c5eb41828bd40cfcdc9fae82171
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3066
_reflns_number_total             4177
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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         0.244
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4177
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0581
_refine_ls_restrained_S_all      1.049
_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)+(0.0576P)²+0.4748P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1467
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
 C4-C3A \\sim C4-C3
 with sigma of 0.02
 C3A-C2 \\sim C3-C2
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C3, C3A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C4, C3, C2
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(H4BC)=Sof(H4BD)=Sof(H2BC)=Sof(H2BD)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=1-FVAR(1)
 Sof(H4AA)=Sof(H4AB)=Sof(H2AA)=Sof(H2AB)=Sof(C3)=Sof(H3A)=Sof(H3B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C21(H21A,H21B), C1(H1A,H1B), C4(H4AA,H4AB), C4(H4BC,H4BD),
 C2(H2AA,H2AB), C2(H2BC,H2BD), C3(H3A,H3B), C3A(H3AA,H3AB)
5.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C6(H6), C13(H13), C18(H18), C16(H16), C9(H9), C17(H17), C12(H12),
 C11(H11), C10(H10)
;
_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 0.4731(2) 0.41084(6) 0.04852(13) 0.0589(4) Uani 1 1 d . . . . .
N2 N 0.49193(19) 0.45093(6) 0.37539(13) 0.0357(3) Uani 1 1 d . . . . .
N1 N 0.42820(19) 0.41496(6) 0.25864(13) 0.0358(3) Uani 1 1 d . . . . .
C14 C 0.5932(2) 0.36700(6) 0.51586(14) 0.0304(3) Uani 1 1 d . . . . .
C7 C 0.4063(2) 0.34430(7) 0.48956(15) 0.0327(3) Uani 1 1 d . . . . .
C15 C 0.6364(2) 0.42033(7) 0.46466(15) 0.0336(4) Uani 1 1 d . . . . .
C8 C 0.3644(2) 0.30678(8) 0.59502(16) 0.0375(4) Uani 1 1 d . . . . .
C19 C 0.7340(2) 0.33610(7) 0.60027(16) 0.0382(4) Uani 1 1 d . . . . .
H19 H 0.7084 0.3004 0.6338 0.046 Uiso 1 1 calc R . . . .
C20 C 0.4974(3) 0.43375(8) 0.15657(16) 0.0417(4) Uani 1 1 d . . . . .
C6 C 0.2693(2) 0.35414(8) 0.38251(16) 0.0398(4) Uani 1 1 d . . . . .
H6 H 0.1589 0.3394 0.3900 0.048 Uiso 1 1 calc R . . . .
C5 C 0.2578(2) 0.38399(8) 0.25348(16) 0.0387(4) Uani 1 1 d . . . . .
C13 C 0.4088(2) 0.32405(9) 0.72745(17) 0.0463(4) Uani 1 1 d . . . . .
H13 H 0.4695 0.3591 0.7518 0.056 Uiso 1 1 calc R . . . .
C18 C 0.9089(2) 0.35643(9) 0.63570(19) 0.0492(5) Uani 1 1 d . . . . .
H18 H 1.0003 0.3343 0.6904 0.059 Uiso 1 1 calc R . . . .
C22 C 0.5383(3) 0.50658(7) 0.32023(18) 0.0449(4) Uani 1 1 d . . . . .
H22A H 0.6307 0.5275 0.3852 0.054 Uiso 1 1 calc R . . . .
H22B H 0.4323 0.5313 0.2917 0.054 Uiso 1 1 calc R . . . .
C21 C 0.6086(3) 0.48786(8) 0.20290(19) 0.0480(5) Uani 1 1 d . . . . .
H21A H 0.5867 0.5176 0.1345 0.058 Uiso 1 1 calc R . . . .
H21B H 0.7371 0.4791 0.2300 0.058 Uiso 1 1 calc R . . . .
C16 C 0.8122(3) 0.44136(8) 0.50464(19) 0.0488(5) Uani 1 1 d . . . . .
H16 H 0.8396 0.4774 0.4738 0.059 Uiso 1 1 calc R . . . .
C9 C 0.2757(3) 0.25409(8) 0.5629(2) 0.0507(5) Uani 1 1 d . . . . .
H9 H 0.2453 0.2415 0.4753 0.061 Uiso 1 1 calc R . . . .
C1 C 0.2094(3) 0.33942(9) 0.13889(18) 0.0515(5) Uani 1 1 d . . . . .
H1A H 0.3182 0.3264 0.1158 0.062 Uiso 1 1 calc R . . . .
H1B H 0.1496 0.3057 0.1647 0.062 Uiso 1 1 calc R . . . .
C17 C 0.9474(3) 0.40971(10) 0.5895(2) 0.0573(5) Uani 1 1 d . . . . .
H17 H 1.0646 0.4245 0.6154 0.069 Uiso 1 1 calc R . . . .
C12 C 0.3639(3) 0.28978(12) 0.8229(2) 0.0627(6) Uani 1 1 d . . . . .
H12 H 0.3934 0.3020 0.9108 0.075 Uiso 1 1 calc R . . . .
C4 C 0.0966(3) 0.42652(10) 0.2184(2) 0.0574(5) Uani 1 1 d D U . . .
H4AA H -0.0047 0.4115 0.2486 0.069 Uiso 0.775(10) 1 calc R . P A 1
H4AB H 0.1307 0.4644 0.2587 0.069 Uiso 0.775(10) 1 calc R . P A 1
H4BC H 0.0388 0.4286 0.2908 0.069 Uiso 0.225(10) 1 calc R . P A 2
H4BD H 0.1384 0.4653 0.2035 0.069 Uiso 0.225(10) 1 calc R . P A 2
C11 C 0.2761(3) 0.23787(13) 0.7887(3) 0.0750(8) Uani 1 1 d . . . . .
H11 H 0.2467 0.2148 0.8533 0.090 Uiso 1 1 calc R . . . .
C10 C 0.2315(3) 0.21996(11) 0.6591(3) 0.0708(7) Uani 1 1 d . . . . .
H10 H 0.1713 0.1847 0.6359 0.085 Uiso 1 1 calc R . . . .
C2 C 0.0833(3) 0.37031(12) 0.0215(2) 0.0755(7) Uani 1 1 d D U . . .
H2AA H -0.0295 0.3490 -0.0085 0.091 Uiso 0.775(10) 1 calc R . P A 1
H2AB H 0.1396 0.3734 -0.0515 0.091 Uiso 0.775(10) 1 calc R . P A 1
H2BC H 0.0113 0.3429 -0.0413 0.091 Uiso 0.225(10) 1 calc R . P A 2
H2BD H 0.1490 0.3959 -0.0238 0.091 Uiso 0.225(10) 1 calc R . P A 2
C3 C 0.0485(7) 0.4309(2) 0.0709(3) 0.0795(15) Uani 0.775(10) 1 d D U P A 1
H3A H 0.1233 0.4599 0.0427 0.095 Uiso 0.775(10) 1 calc R . P A 1
H3B H -0.0778 0.4417 0.0369 0.095 Uiso 0.775(10) 1 calc R . P A 1
C3A C -0.0342(15) 0.4052(6) 0.0968(13) 0.067(4) Uani 0.225(10) 1 d D U P A 2
H3AA H -0.0948 0.4375 0.0436 0.080 Uiso 0.225(10) 1 calc R . P A 2
H3AB H -0.1246 0.3802 0.1189 0.080 Uiso 0.225(10) 1 calc R . P A 2


_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 C20 1.215(2) . ?
N2 N1 1.4482(18) . ?
N2 C15 1.431(2) . ?
N2 C22 1.480(2) . ?
N1 C20 1.376(2) . ?
N1 C5 1.472(2) . ?
C14 C7 1.477(2) . ?
C14 C15 1.407(2) . ?
C14 C19 1.395(2) . ?
C7 C8 1.495(2) . ?
C7 C6 1.338(2) . ?
C15 C16 1.387(2) . ?
C8 C13 1.393(2) . ?
C8 C9 1.384(3) . ?
C19 H19 0.9300 . ?
C19 C18 1.373(2) . ?
C20 C21 1.511(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.493(2) . ?
C5 C1 1.544(2) . ?
C5 C4 1.539(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.380(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.373(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C21 1.521(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C16 H16 0.9300 . ?
C16 C17 1.380(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.524(3) . ?
C17 H17 0.9300 . ?
C12 H12 0.9300 . ?
C12 C11 1.368(4) . ?
C4 H4AA 0.9700 . ?
C4 H4AB 0.9700 . ?
C4 H4BC 0.9700 . ?
C4 H4BD 0.9700 . ?
C4 C3 1.492(4) . ?
C4 C3A 1.481(9) . ?
C11 H11 0.9300 . ?
C11 C10 1.370(4) . ?
C10 H10 0.9300 . ?
C2 H2AA 0.9700 . ?
C2 H2AB 0.9700 . ?
C2 H2BC 0.9700 . ?
C2 H2BD 0.9700 . ?
C2 C3 1.529(5) . ?
C2 C3A 1.558(11) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3A H3AA 0.9700 . ?
C3A H3AB 0.9700 . ?

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
N1 N2 C22 103.05(12) . . ?
C15 N2 N1 107.70(12) . . ?
C15 N2 C22 117.03(14) . . ?
N2 N1 C5 114.06(12) . . ?
C20 N1 N2 111.14(13) . . ?
C20 N1 C5 129.52(14) . . ?
C15 C14 C7 123.06(14) . . ?
C19 C14 C7 119.28(14) . . ?
C19 C14 C15 117.58(15) . . ?
C14 C7 C8 116.47(13) . . ?
C6 C7 C14 127.27(14) . . ?
C6 C7 C8 116.25(14) . . ?
C14 C15 N2 117.16(14) . . ?
C16 C15 N2 123.35(15) . . ?
C16 C15 C14 119.46(15) . . ?
C13 C8 C7 121.58(16) . . ?
C9 C8 C7 120.54(16) . . ?
C9 C8 C13 117.86(16) . . ?
C14 C19 H19 118.8 . . ?
C18 C19 C14 122.41(16) . . ?
C18 C19 H19 118.8 . . ?
O1 C20 N1 125.93(17) . . ?
O1 C20 C21 126.25(16) . . ?
N1 C20 C21 107.82(14) . . ?
C7 C6 H6 113.5 . . ?
C7 C6 C5 133.00(16) . . ?
C5 C6 H6 113.5 . . ?
N1 C5 C6 110.03(13) . . ?
N1 C5 C1 112.34(14) . . ?
N1 C5 C4 110.42(15) . . ?
C6 C5 C1 110.02(15) . . ?
C6 C5 C4 111.24(15) . . ?
C4 C5 C1 102.61(15) . . ?
C8 C13 H13 119.6 . . ?
C12 C13 C8 120.8(2) . . ?
C12 C13 H13 119.6 . . ?
C19 C18 H18 120.3 . . ?
C19 C18 C17 119.30(18) . . ?
C17 C18 H18 120.3 . . ?
N2 C22 H22A 111.0 . . ?
N2 C22 H22B 111.0 . . ?
N2 C22 C21 103.87(13) . . ?
H22A C22 H22B 109.0 . . ?
C21 C22 H22A 111.0 . . ?
C21 C22 H22B 111.0 . . ?
C20 C21 C22 101.75(14) . . ?
C20 C21 H21A 111.4 . . ?
C20 C21 H21B 111.4 . . ?
C22 C21 H21A 111.4 . . ?
C22 C21 H21B 111.4 . . ?
H21A C21 H21B 109.3 . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 121.09(17) . . ?
C17 C16 H16 119.5 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 120.9(2) . . ?
C10 C9 H9 119.5 . . ?
C5 C1 H1A 110.3 . . ?
C5 C1 H1B 110.3 . . ?
H1A C1 H1B 108.6 . . ?
C2 C1 C5 106.90(17) . . ?
C2 C1 H1A 110.3 . . ?
C2 C1 H1B 110.3 . . ?
C18 C17 C16 120.05(18) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C13 C12 H12 119.9 . . ?
C11 C12 C13 120.2(2) . . ?
C11 C12 H12 119.9 . . ?
C5 C4 H4AA 110.8 . . ?
C5 C4 H4AB 110.8 . . ?
C5 C4 H4BC 110.0 . . ?
C5 C4 H4BD 110.0 . . ?
H4AA C4 H4AB 108.8 . . ?
H4BC C4 H4BD 108.4 . . ?
C3 C4 C5 104.9(2) . . ?
C3 C4 H4AA 110.8 . . ?
C3 C4 H4AB 110.8 . . ?
C3A C4 C5 108.4(4) . . ?
C3A C4 H4BC 110.0 . . ?
C3A C4 H4BD 110.0 . . ?
C12 C11 H11 120.0 . . ?
C12 C11 C10 119.91(19) . . ?
C10 C11 H11 120.0 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C1 C2 H2AA 110.5 . . ?
C1 C2 H2AB 110.5 . . ?
C1 C2 H2BC 111.9 . . ?
C1 C2 H2BD 111.9 . . ?
C1 C2 C3 106.27(19) . . ?
C1 C2 C3A 99.2(5) . . ?
H2AA C2 H2AB 108.7 . . ?
H2BC C2 H2BD 109.6 . . ?
C3 C2 H2AA 110.5 . . ?
C3 C2 H2AB 110.5 . . ?
C3A C2 H2BC 111.9 . . ?
C3A C2 H2BD 111.9 . . ?
C4 C3 C2 105.6(3) . . ?
C4 C3 H3A 110.6 . . ?
C4 C3 H3B 110.6 . . ?
C2 C3 H3A 110.6 . . ?
C2 C3 H3B 110.6 . . ?
H3A C3 H3B 108.8 . . ?
C4 C3A C2 104.7(6) . . ?
C4 C3A H3AA 110.8 . . ?
C4 C3A H3AB 110.8 . . ?
C2 C3A H3AA 110.8 . . ?
C2 C3A H3AB 110.8 . . ?
H3AA C3A H3AB 108.9 . . ?

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 C20 C21 C22 161.50(18) . . . . ?
N2 N1 C20 O1 177.12(16) . . . . ?
N2 N1 C20 C21 -2.94(18) . . . . ?
N2 N1 C5 C6 -48.66(17) . . . . ?
N2 N1 C5 C1 -171.60(13) . . . . ?
N2 N1 C5 C4 74.52(17) . . . . ?
N2 C15 C16 C17 -179.03(17) . . . . ?
N2 C22 C21 C20 32.29(18) . . . . ?
N1 N2 C15 C14 -63.76(16) . . . . ?
N1 N2 C15 C16 118.00(17) . . . . ?
N1 N2 C22 C21 -34.31(17) . . . . ?
N1 C20 C21 C22 -18.43(19) . . . . ?
N1 C5 C1 C2 -94.18(19) . . . . ?
N1 C5 C4 C3 83.4(3) . . . . ?
N1 C5 C4 C3A 122.3(8) . . . . ?
C14 C7 C8 C13 49.6(2) . . . . ?
C14 C7 C8 C9 -131.99(17) . . . . ?
C14 C7 C6 C5 7.0(3) . . . . ?
C14 C15 C16 C17 2.8(3) . . . . ?
C14 C19 C18 C17 1.6(3) . . . . ?
C7 C14 C15 N2 -4.8(2) . . . . ?
C7 C14 C15 C16 173.56(15) . . . . ?
C7 C14 C19 C18 -175.81(16) . . . . ?
C7 C8 C13 C12 177.84(17) . . . . ?
C7 C8 C9 C10 -178.00(18) . . . . ?
C7 C6 C5 N1 -10.1(3) . . . . ?
C7 C6 C5 C1 114.2(2) . . . . ?
C7 C6 C5 C4 -132.8(2) . . . . ?
C15 N2 N1 C20 -100.54(15) . . . . ?
C15 N2 N1 C5 102.57(14) . . . . ?
C15 N2 C22 C21 83.63(18) . . . . ?
C15 C14 C7 C8 -150.34(15) . . . . ?
C15 C14 C7 C6 28.8(3) . . . . ?
C15 C14 C19 C18 1.2(2) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C8 C7 C6 C5 -173.94(18) . . . . ?
C8 C13 C12 C11 0.6(3) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C19 C14 C7 C8 26.5(2) . . . . ?
C19 C14 C7 C6 -154.42(17) . . . . ?
C19 C14 C15 N2 178.38(13) . . . . ?
C19 C14 C15 C16 -3.3(2) . . . . ?
C19 C18 C17 C16 -2.2(3) . . . . ?
C20 N1 C5 C6 159.68(16) . . . . ?
C20 N1 C5 C1 36.7(2) . . . . ?
C20 N1 C5 C4 -77.1(2) . . . . ?
C6 C7 C8 C13 -129.57(18) . . . . ?
C6 C7 C8 C9 48.8(2) . . . . ?
C6 C5 C1 C2 142.87(17) . . . . ?
C6 C5 C4 C3 -154.2(3) . . . . ?
C6 C5 C4 C3A -115.2(8) . . . . ?
C5 N1 C20 O1 -30.6(3) . . . . ?
C5 N1 C20 C21 149.38(16) . . . . ?
C5 C1 C2 C3 -3.8(3) . . . . ?
C5 C1 C2 C3A -40.0(6) . . . . ?
C5 C4 C3 C2 35.0(4) . . . . ?
C5 C4 C3A C2 -27.4(12) . . . . ?
C13 C8 C9 C10 0.4(3) . . . . ?
C13 C12 C11 C10 -0.4(3) . . . . ?
C22 N2 N1 C20 23.77(17) . . . . ?
C22 N2 N1 C5 -133.12(14) . . . . ?
C22 N2 C15 C14 -179.16(13) . . . . ?
C22 N2 C15 C16 2.6(2) . . . . ?
C9 C8 C13 C12 -0.6(3) . . . . ?
C1 C5 C4 C3 -36.6(3) . . . . ?
C1 C5 C4 C3A 2.3(8) . . . . ?
C1 C2 C3 C4 -19.2(4) . . . . ?
C1 C2 C3A C4 40.8(10) . . . . ?
C12 C11 C10 C9 0.3(4) . . . . ?
C4 C5 C1 C2 24.4(2) . . . . ?


_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 1.304
_oxdiff_exptl_absorpt_empirical_full_min 0.702
