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

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

data_baow2_0717
_database_code_depnum_ccdc_archive 'CCDC 1941766'
loop_
_audit_author_name
_audit_author_address
baowen
;LanZhou University
China
;
_audit_update_record             
;
2019-07-19 deposited with the CCDC.	2020-05-25 downloaded from the CCDC.
;
_audit_creation_date             2019-07-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 N3'
_chemical_formula_sum            'C18 H15 N3'
_chemical_formula_weight         273.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.2710(2)
_cell_length_b                   9.9844(2)
_cell_length_c                   18.3806(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.740(2)
_cell_angle_gamma                90
_cell_volume                     1480.52(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5489
_cell_measurement_temperature    293.1(2)
_cell_measurement_theta_max      69.7950
_cell_measurement_theta_min      5.4770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.226
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11117
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        66.587
_diffrn_reflns_theta_max         66.587
_diffrn_reflns_theta_min         5.070
_diffrn_ambient_temperature      293.1(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -87.00  -45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  -30.0000 42

#__ type_ start__ end____ width___ exp.time_
  2 omega  -87.00  -62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega  -83.00  -44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  120.0000 39

#__ type_ start__ end____ width___ exp.time_
  4 omega   65.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -150.0000 52

#__ type_ start__ end____ width___ exp.time_
  5 omega   27.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -180.0000 57

#__ type_ start__ end____ width___ exp.time_
  6 omega   35.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 77

#__ type_ start__ end____ width___ exp.time_
  7 omega   53.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 32

#__ type_ start__ end____ width___ exp.time_
  8 omega   64.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 44

#__ type_ start__ end____ width___ exp.time_
  9 omega   51.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
 10 omega   36.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega  119.00  167.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000    0.0000 48

#__ type_ start__ end____ width___ exp.time_
 12 omega   50.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000 -120.0000 49

#__ type_ start__ end____ width___ exp.time_
 13 omega  -66.00  -40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  125.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega  -82.00  -43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  -90.0000 39

#__ type_ start__ end____ width___ exp.time_
 15 omega   85.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
 16 omega   23.00   79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  -90.0000 56

#__ type_ start__ end____ width___ exp.time_
 17 omega   66.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   32.00   58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   54.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega  139.00  171.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  120.0000 32

#__ type_ start__ end____ width___ exp.time_
 21 omega   92.00  139.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000 -120.0000 47

#__ type_ start__ end____ width___ exp.time_
 22 omega   85.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 23 omega   43.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000 -120.0000 33

#__ type_ start__ end____ width___ exp.time_
 24 omega   59.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   60.0000 40

#__ type_ start__ end____ width___ exp.time_
 25 omega   67.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 26 omega   60.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 27 omega   56.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -30.0000 38

#__ type_ start__ end____ width___ exp.time_
 28 omega   33.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   77.0000  -60.0000 29

#__ type_ start__ end____ width___ exp.time_
 29 omega   -1.00   25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   77.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 30 omega   27.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   77.0000   30.0000 29

#__ type_ start__ end____ width___ exp.time_
 31 omega  -18.00    8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   77.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 32 omega   34.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  150.0000 88

#__ type_ start__ end____ width___ exp.time_
 33 omega   69.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -90.0000 42

#__ type_ start__ end____ width___ exp.time_
 34 omega   17.00   49.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000    0.0000 32

#__ type_ start__ end____ width___ exp.time_
 35 omega   64.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000 -180.0000 46

#__ type_ start__ end____ width___ exp.time_
 36 omega   52.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000   60.0000 47

#__ type_ start__ end____ width___ exp.time_
 37 omega   35.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 46

#__ type_ start__ end____ width___ exp.time_
 38 omega  138.00  170.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 39 omega   94.00  168.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  150.0000 74

#__ type_ start__ end____ width___ exp.time_
 40 omega  140.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 38

#__ type_ start__ end____ width___ exp.time_
 41 omega  103.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 42 omega   66.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 43 omega   60.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 44 omega  108.00  151.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 43

#__ type_ start__ end____ width___ exp.time_
 45 omega   78.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -60.0000 32

#__ type_ start__ end____ width___ exp.time_
 46 omega   84.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 31

#__ type_ start__ end____ width___ exp.time_
 47 omega   44.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 48 omega   58.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 49 omega  127.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 49

#__ type_ start__ end____ width___ exp.time_
 50 omega   85.00  142.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -60.0000 57
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1071322000
_diffrn_orient_matrix_UB_12      0.0115923000
_diffrn_orient_matrix_UB_13      0.0584632000
_diffrn_orient_matrix_UB_21      -0.0397952000
_diffrn_orient_matrix_UB_22      0.1467295000
_diffrn_orient_matrix_UB_23      -0.0230612000
_diffrn_orient_matrix_UB_31      -0.1530402000
_diffrn_orient_matrix_UB_32      -0.0462613000
_diffrn_orient_matrix_UB_33      -0.0585916000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2341
_reflns_number_total             2566
_reflns_odcompleteness_completeness 98.18
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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         0.158
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2566
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0433
_refine_ls_restrained_S_all      1.059
_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)+(0.0707P)²+0.2406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1215
_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 Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C12(H12), C15(H15), C16(H16), C19(H19), C21(H21)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_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
N1 N 0.17224(14) 0.32028(11) 0.07773(6) 0.0416(3) Uani 1 1 d . . . . .
C2 C 0.26274(16) 0.19486(13) 0.08353(7) 0.0392(3) Uani 1 1 d . . . . .
H2 H 0.181038 0.122219 0.075543 0.047 Uiso 1 1 calc R . . . .
C3 C 0.27999(15) 0.15048(12) -0.04979(7) 0.0361(3) Uani 1 1 d . . . . .
C4 C 0.10437(15) 0.12368(12) -0.06618(7) 0.0396(3) Uani 1 1 d . . . . .
C5 C 0.05608(15) 0.33939(13) 0.12234(7) 0.0390(3) Uani 1 1 d . . . . .
C6 C 0.37191(18) 0.17564(14) 0.15896(8) 0.0481(3) Uani 1 1 d . . . . .
C7 C 0.53488(17) 0.16288(15) -0.09027(8) 0.0498(4) Uani 1 1 d . . . . .
H7 H 0.594135 0.156436 -0.127649 0.060 Uiso 1 1 calc R . . . .
N8 N -0.03449(15) 0.10062(14) -0.08082(8) 0.0559(3) Uani 1 1 d . . . . .
C9 C 0.36162(16) 0.18363(12) 0.02315(7) 0.0390(3) Uani 1 1 d . . . . .
C10 C 0.61657(18) 0.19592(17) -0.01898(9) 0.0563(4) Uani 1 1 d . . . . .
H10 H 0.730255 0.211250 -0.008636 0.068 Uiso 1 1 calc R . . . .
C11 C 0.36491(16) 0.13893(13) -0.10733(7) 0.0403(3) Uani 1 1 d . . . . .
C12 C -0.02829(15) 0.24412(14) 0.15424(7) 0.0444(3) Uani 1 1 d . . . . .
H12 H -0.009601 0.153148 0.148956 0.053 Uiso 1 1 calc R . . . .
N13 N 0.45194(19) 0.16324(17) 0.21749(8) 0.0707(4) Uani 1 1 d . . . . .
C14 C 0.03053(18) 0.47578(14) 0.13136(8) 0.0500(4) Uani 1 1 d . . . . .
C15 C -0.14191(18) 0.28878(18) 0.19444(8) 0.0563(4) Uani 1 1 d . . . . .
H15 H -0.199013 0.226458 0.216807 0.068 Uiso 1 1 calc R . . . .
C16 C 0.53046(17) 0.20657(17) 0.03772(8) 0.0512(4) Uani 1 1 d . . . . .
H16 H 0.586765 0.229253 0.085701 0.061 Uiso 1 1 calc R . . . .
C17 C 0.27782(19) 0.09897(16) -0.18469(8) 0.0523(4) Uani 1 1 d . . . . .
H17A H 0.219473 0.016393 -0.182736 0.078 Uiso 1 1 calc GR . . . .
H17B H 0.357743 0.087280 -0.214934 0.078 Uiso 1 1 calc GR . . . .
H17C H 0.200496 0.167646 -0.205938 0.078 Uiso 1 1 calc GR . . . .
C18 C 0.2671(2) 0.44645(15) 0.08041(10) 0.0590(4) Uani 1 1 d . . . . .
H18A H 0.300994 0.461787 0.033829 0.071 Uiso 1 1 calc R . . . .
H18B H 0.364689 0.445133 0.120919 0.071 Uiso 1 1 calc R . . . .
C19 C -0.1717(2) 0.4231(2) 0.20185(10) 0.0663(5) Uani 1 1 d . . . . .
H19 H -0.249925 0.450567 0.228113 0.080 Uiso 1 1 calc R . . . .
C20 C 0.1440(2) 0.55333(15) 0.09340(10) 0.0640(4) Uani 1 1 d . . . . .
H20A H 0.199634 0.624725 0.125080 0.077 Uiso 1 1 calc R . . . .
H20B H 0.083893 0.591210 0.046620 0.077 Uiso 1 1 calc R . . . .
C21 C -0.0854(2) 0.51728(18) 0.17028(9) 0.0638(5) Uani 1 1 d . . . . .
H21 H -0.105456 0.608116 0.175250 0.077 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
N1 C2 1.4508(16) . ?
N1 C5 1.4068(17) . ?
N1 C18 1.4792(18) . ?
C2 H2 0.9800 . ?
C2 C6 1.4907(18) . ?
C2 C9 1.5210(17) . ?
C3 C4 1.4419(17) . ?
C3 C9 1.4012(18) . ?
C3 C11 1.3975(18) . ?
C4 N8 1.1438(17) . ?
C5 C12 1.3843(19) . ?
C5 C14 1.3936(19) . ?
C6 N13 1.139(2) . ?
C7 H7 0.9300 . ?
C7 C10 1.375(2) . ?
C7 C11 1.3919(19) . ?
C9 C16 1.3818(19) . ?
C10 H10 0.9300 . ?
C10 C16 1.390(2) . ?
C11 C17 1.4994(18) . ?
C12 H12 0.9300 . ?
C12 C15 1.391(2) . ?
C14 C20 1.502(2) . ?
C14 C21 1.381(2) . ?
C15 H15 0.9300 . ?
C15 C19 1.376(2) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C20 1.530(2) . ?
C19 H19 0.9300 . ?
C19 C21 1.383(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21 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 N1 C18 118.12(11) . . ?
C5 N1 C2 118.81(10) . . ?
C5 N1 C18 106.89(11) . . ?
N1 C2 H2 107.5 . . ?
N1 C2 C6 112.10(11) . . ?
N1 C2 C9 111.21(10) . . ?
C6 C2 H2 107.5 . . ?
C6 C2 C9 110.87(10) . . ?
C9 C2 H2 107.5 . . ?
C9 C3 C4 119.63(11) . . ?
C11 C3 C4 118.54(11) . . ?
C11 C3 C9 121.80(11) . . ?
N8 C4 C3 178.20(14) . . ?
C12 C5 N1 128.80(12) . . ?
C12 C5 C14 121.15(13) . . ?
C14 C5 N1 110.05(12) . . ?
N13 C6 C2 177.88(15) . . ?
C10 C7 H7 119.5 . . ?
C10 C7 C11 121.02(13) . . ?
C11 C7 H7 119.5 . . ?
C3 C9 C2 119.49(11) . . ?
C16 C9 C2 121.97(12) . . ?
C16 C9 C3 118.54(12) . . ?
C7 C10 H10 119.8 . . ?
C7 C10 C16 120.49(13) . . ?
C16 C10 H10 119.8 . . ?
C3 C11 C17 121.54(12) . . ?
C7 C11 C3 117.81(12) . . ?
C7 C11 C17 120.63(12) . . ?
C5 C12 H12 121.1 . . ?
C5 C12 C15 117.88(14) . . ?
C15 C12 H12 121.1 . . ?
C5 C14 C20 108.77(13) . . ?
C21 C14 C5 119.73(15) . . ?
C21 C14 C20 131.50(15) . . ?
C12 C15 H15 119.3 . . ?
C19 C15 C12 121.46(16) . . ?
C19 C15 H15 119.3 . . ?
C9 C16 C10 120.34(13) . . ?
C9 C16 H16 119.8 . . ?
C10 C16 H16 119.8 . . ?
C11 C17 H17A 109.5 . . ?
C11 C17 H17B 109.5 . . ?
C11 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 H18A 111.1 . . ?
N1 C18 H18B 111.1 . . ?
N1 C18 C20 103.46(13) . . ?
H18A C18 H18B 109.0 . . ?
C20 C18 H18A 111.1 . . ?
C20 C18 H18B 111.1 . . ?
C15 C19 H19 120.0 . . ?
C15 C19 C21 120.08(15) . . ?
C21 C19 H19 120.0 . . ?
C14 C20 C18 102.62(12) . . ?
C14 C20 H20A 111.2 . . ?
C14 C20 H20B 111.2 . . ?
C18 C20 H20A 111.2 . . ?
C18 C20 H20B 111.2 . . ?
H20A C20 H20B 109.2 . . ?
C14 C21 C19 119.66(15) . . ?
C14 C21 H21 120.2 . . ?
C19 C21 H21 120.2 . . ?

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
N1 C2 C9 C3 -77.44(14) . . . . ?
N1 C2 C9 C16 101.86(14) . . . . ?
N1 C5 C12 C15 -177.95(12) . . . . ?
N1 C5 C14 C20 -3.08(15) . . . . ?
N1 C5 C14 C21 176.77(12) . . . . ?
N1 C18 C20 C14 25.63(16) . . . . ?
C2 N1 C5 C12 -23.55(18) . . . . ?
C2 N1 C5 C14 157.21(11) . . . . ?
C2 N1 C18 C20 -165.78(12) . . . . ?
C2 C9 C16 C10 -179.72(13) . . . . ?
C3 C9 C16 C10 -0.4(2) . . . . ?
C4 C3 C9 C2 -1.79(17) . . . . ?
C4 C3 C9 C16 178.88(12) . . . . ?
C4 C3 C11 C7 -178.91(11) . . . . ?
C4 C3 C11 C17 -0.32(18) . . . . ?
C5 N1 C2 C6 -64.11(15) . . . . ?
C5 N1 C2 C9 171.14(10) . . . . ?
C5 N1 C18 C20 -28.62(15) . . . . ?
C5 C12 C15 C19 0.7(2) . . . . ?
C5 C14 C20 C18 -14.57(16) . . . . ?
C5 C14 C21 C19 1.9(2) . . . . ?
C6 C2 C9 C3 157.11(12) . . . . ?
C6 C2 C9 C16 -23.58(17) . . . . ?
C7 C10 C16 C9 0.2(2) . . . . ?
C9 C3 C11 C7 -0.66(18) . . . . ?
C9 C3 C11 C17 177.93(12) . . . . ?
C10 C7 C11 C3 0.4(2) . . . . ?
C10 C7 C11 C17 -178.17(14) . . . . ?
C11 C3 C9 C2 179.98(11) . . . . ?
C11 C3 C9 C16 0.65(19) . . . . ?
C11 C7 C10 C16 -0.2(2) . . . . ?
C12 C5 C14 C20 177.61(12) . . . . ?
C12 C5 C14 C21 -2.5(2) . . . . ?
C12 C15 C19 C21 -1.3(2) . . . . ?
C14 C5 C12 C15 1.22(18) . . . . ?
C15 C19 C21 C14 0.0(2) . . . . ?
C18 N1 C2 C6 67.95(15) . . . . ?
C18 N1 C2 C9 -56.80(15) . . . . ?
C18 N1 C5 C12 -160.36(13) . . . . ?
C18 N1 C5 C14 20.39(14) . . . . ?
C20 C14 C21 C19 -178.29(16) . . . . ?
C21 C14 C20 C18 165.61(15) . . . . ?

_olex2_date_sample_data_collection 2019-07-17
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_baow1_0717
_database_code_depnum_ccdc_archive 'CCDC 1941767'
loop_
_audit_author_name
_audit_author_address
baowen
;LanZhou University
China
;
_audit_update_record             
;
2019-07-19 deposited with the CCDC.	2020-05-25 downloaded from the CCDC.
;
_audit_creation_date             2019-07-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 N3 O'
_chemical_formula_sum            'C18 H15 N3 O'
_chemical_formula_weight         289.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   9.2780(4)
_cell_length_b                   23.2807(7)
_cell_length_c                   7.4089(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.520(4)
_cell_angle_gamma                90
_cell_volume                     1562.25(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2267
_cell_measurement_temperature    292.77(10)
_cell_measurement_theta_max      69.6450
_cell_measurement_theta_min      8.9480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.628
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5181
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        66.592
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_min         3.797
_diffrn_ambient_temperature      292.77(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -31.00   11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -38.0000  120.0000 42

#__ type_ start__ end____ width___ exp.time_
  2 omega  -75.00  -35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  -90.0000 40

#__ type_ start__ end____ width___ exp.time_
  3 omega  -80.00  -54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -38.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   45.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000   90.0000 33

#__ type_ start__ end____ width___ exp.time_
  5 omega   -9.00   38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000   90.0000 47

#__ type_ start__ end____ width___ exp.time_
  6 omega   67.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
  7 omega  -14.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000   30.0000 89

#__ type_ start__ end____ width___ exp.time_
  8 omega   45.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  9 omega   57.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 36

#__ type_ start__ end____ width___ exp.time_
 10 omega   36.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000    0.0000 29

#__ type_ start__ end____ width___ exp.time_
 11 omega   36.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  120.0000 55

#__ type_ start__ end____ width___ exp.time_
 12 omega  107.00  151.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   60.0000 44

#__ type_ start__ end____ width___ exp.time_
 13 omega   38.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 57

#__ type_ start__ end____ width___ exp.time_
 14 omega   37.00   79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
 15 omega   46.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 28

#__ type_ start__ end____ width___ exp.time_
 16 omega   53.00  123.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000   30.0000 70

#__ type_ start__ end____ width___ exp.time_
 17 omega   37.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 56

#__ type_ start__ end____ width___ exp.time_
 18 omega   54.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   90.0000 33

#__ type_ start__ end____ width___ exp.time_
 19 omega   44.00   69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 20 omega   74.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 27
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1634652000
_diffrn_orient_matrix_UB_12      0.0180680000
_diffrn_orient_matrix_UB_13      -0.0546447000
_diffrn_orient_matrix_UB_21      0.0135938000
_diffrn_orient_matrix_UB_22      0.0067006000
_diffrn_orient_matrix_UB_23      -0.2025816000
_diffrn_orient_matrix_UB_31      -0.0452365000
_diffrn_orient_matrix_UB_32      -0.0632539000
_diffrn_orient_matrix_UB_33      -0.0370776000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2277
_reflns_number_total             2690
_reflns_odcompleteness_completeness 96.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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         0.166
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2690
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0454
_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)+(0.0724P)²+0.2012P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1337
_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 Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C12(H12), C14(H14), C18(H18), C20(H20), C22(H22)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_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
N1 N 0.28405(14) 0.35881(5) 0.66674(17) 0.0469(3) Uani 1 1 d . . . . .
C2 C 0.41445(17) 0.33877(6) 0.7821(2) 0.0473(4) Uani 1 1 d . . . . .
C3 C 0.01902(16) 0.37793(6) 0.60249(19) 0.0428(3) Uani 1 1 d . . . . .
C4 C -0.06399(19) 0.37135(7) 0.4251(2) 0.0561(4) Uani 1 1 d . . . . .
H4 H -0.045163 0.340240 0.354887 0.067 Uiso 1 1 calc R . . . .
C5 C 0.11231(17) 0.27788(7) 0.6199(2) 0.0496(4) Uani 1 1 d . . . . .
C6 C 0.14234(16) 0.33777(6) 0.6899(2) 0.0432(3) Uani 1 1 d . . . . .
H6 H 0.145408 0.337055 0.822919 0.052 Uiso 1 1 calc R . . . .
O7 O -0.31361(16) 0.49512(6) 0.39377(19) 0.0749(4) Uani 1 1 d . . . . .
C8 C -0.12348(19) 0.46388(7) 0.6292(2) 0.0529(4) Uani 1 1 d . . . . .
H8 H -0.143190 0.494985 0.698821 0.063 Uiso 1 1 calc R . . . .
C9 C -0.20529(18) 0.45568(7) 0.4509(2) 0.0523(4) Uani 1 1 d . . . . .
C10 C -0.01229(17) 0.42550(6) 0.70287(19) 0.0452(4) Uani 1 1 d . . . . .
N11 N 0.09168(18) 0.23197(6) 0.5684(2) 0.0678(4) Uani 1 1 d . . . . .
C12 C -0.1744(2) 0.40970(7) 0.3486(2) 0.0580(4) Uani 1 1 d . . . . .
H12 H -0.227801 0.404406 0.228135 0.070 Uiso 1 1 calc R . . . .
C13 C 0.5333(2) 0.34701(7) 0.6964(3) 0.0614(5) Uani 1 1 d . . . . .
C14 C 0.4356(2) 0.31574(7) 0.9580(3) 0.0589(4) Uani 1 1 d . . . . .
H14 H 0.356594 0.310507 1.015026 0.071 Uiso 1 1 calc R . . . .
C15 C 0.0725(2) 0.43416(7) 0.8885(2) 0.0611(5) Uani 1 1 d . . . . .
N17 N 0.1407(3) 0.43990(9) 1.0344(2) 0.0947(7) Uani 1 1 d . . . . .
C16 C 0.3095(2) 0.36296(8) 0.4773(2) 0.0613(4) Uani 1 1 d . . . . .
H16A H 0.254473 0.394662 0.410451 0.074 Uiso 1 1 calc R . . . .
H16B H 0.281567 0.327668 0.409076 0.074 Uiso 1 1 calc R . . . .
C18 C 0.5785(2) 0.30062(9) 1.0474(3) 0.0756(6) Uani 1 1 d . . . . .
H18 H 0.595079 0.284742 1.165247 0.091 Uiso 1 1 calc R . . . .
C19 C -0.4026(3) 0.48996(10) 0.2120(3) 0.0864(7) Uani 1 1 d . . . . .
H19A H -0.340674 0.490451 0.123660 0.130 Uiso 1 1 calc GR . . . .
H19B H -0.470787 0.521495 0.188111 0.130 Uiso 1 1 calc GR . . . .
H19C H -0.456436 0.454458 0.201565 0.130 Uiso 1 1 calc GR . . . .
C20 C 0.6735(2) 0.33240(10) 0.7881(4) 0.0803(7) Uani 1 1 d . . . . .
H20 H 0.753026 0.338325 0.732564 0.096 Uiso 1 1 calc R . . . .
C21 C 0.4757(2) 0.37331(10) 0.5091(3) 0.0741(6) Uani 1 1 d . . . . .
H21A H 0.517044 0.354478 0.415088 0.089 Uiso 1 1 calc R . . . .
H21B H 0.497885 0.414029 0.509605 0.089 Uiso 1 1 calc R . . . .
C22 C 0.6959(2) 0.30892(10) 0.9629(4) 0.0849(7) Uani 1 1 d . . . . .
H22 H 0.790712 0.298594 1.024431 0.102 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
N1 C2 1.401(2) . ?
N1 C6 1.4476(19) . ?
N1 C16 1.476(2) . ?
C2 C13 1.400(2) . ?
C2 C14 1.383(2) . ?
C3 C4 1.380(2) . ?
C3 C6 1.510(2) . ?
C3 C10 1.399(2) . ?
C4 H4 0.9300 . ?
C4 C12 1.385(2) . ?
C5 C6 1.492(2) . ?
C5 N11 1.137(2) . ?
C6 H6 0.9800 . ?
O7 C9 1.359(2) . ?
O7 C19 1.424(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.387(2) . ?
C8 C10 1.384(2) . ?
C9 C12 1.377(2) . ?
C10 C15 1.443(2) . ?
C12 H12 0.9300 . ?
C13 C20 1.373(3) . ?
C13 C21 1.505(3) . ?
C14 H14 0.9300 . ?
C14 C18 1.392(3) . ?
C15 N17 1.135(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C21 1.528(3) . ?
C18 H18 0.9300 . ?
C18 C22 1.383(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20 0.9300 . ?
C20 C22 1.380(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22 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 N1 C6 120.08(12) . . ?
C2 N1 C16 107.87(13) . . ?
C6 N1 C16 118.12(13) . . ?
C13 C2 N1 109.79(15) . . ?
C14 C2 N1 129.13(14) . . ?
C14 C2 C13 121.04(16) . . ?
C4 C3 C6 123.64(13) . . ?
C4 C3 C10 117.17(14) . . ?
C10 C3 C6 119.16(13) . . ?
C3 C4 H4 119.0 . . ?
C3 C4 C12 121.94(15) . . ?
C12 C4 H4 119.0 . . ?
N11 C5 C6 178.84(19) . . ?
N1 C6 C3 111.27(12) . . ?
N1 C6 C5 112.39(12) . . ?
N1 C6 H6 107.2 . . ?
C3 C6 H6 107.2 . . ?
C5 C6 C3 111.24(13) . . ?
C5 C6 H6 107.2 . . ?
C9 O7 C19 118.39(15) . . ?
C9 C8 H8 120.2 . . ?
C10 C8 H8 120.2 . . ?
C10 C8 C9 119.61(14) . . ?
O7 C9 C8 114.74(14) . . ?
O7 C9 C12 125.56(15) . . ?
C12 C9 C8 119.68(15) . . ?
C3 C10 C15 118.94(14) . . ?
C8 C10 C3 121.60(14) . . ?
C8 C10 C15 119.45(14) . . ?
C4 C12 H12 120.0 . . ?
C9 C12 C4 119.97(15) . . ?
C9 C12 H12 120.0 . . ?
C2 C13 C21 108.44(16) . . ?
C20 C13 C2 119.7(2) . . ?
C20 C13 C21 131.81(19) . . ?
C2 C14 H14 120.9 . . ?
C2 C14 C18 118.16(19) . . ?
C18 C14 H14 120.9 . . ?
N17 C15 C10 178.57(19) . . ?
N1 C16 H16A 111.1 . . ?
N1 C16 H16B 111.1 . . ?
N1 C16 C21 103.16(15) . . ?
H16A C16 H16B 109.1 . . ?
C21 C16 H16A 111.1 . . ?
C21 C16 H16B 111.1 . . ?
C14 C18 H18 119.6 . . ?
C22 C18 C14 120.8(2) . . ?
C22 C18 H18 119.6 . . ?
O7 C19 H19A 109.5 . . ?
O7 C19 H19B 109.5 . . ?
O7 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C13 C20 H20 120.1 . . ?
C13 C20 C22 119.8(2) . . ?
C22 C20 H20 120.1 . . ?
C13 C21 C16 102.91(14) . . ?
C13 C21 H21A 111.2 . . ?
C13 C21 H21B 111.2 . . ?
C16 C21 H21A 111.2 . . ?
C16 C21 H21B 111.2 . . ?
H21A C21 H21B 109.1 . . ?
C18 C22 H22 119.8 . . ?
C20 C22 C18 120.44(19) . . ?
C20 C22 H22 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
N1 C2 C13 C20 177.52(16) . . . . ?
N1 C2 C13 C21 -1.27(19) . . . . ?
N1 C2 C14 C18 -177.84(16) . . . . ?
N1 C16 C21 C13 25.58(19) . . . . ?
C2 N1 C6 C3 160.35(12) . . . . ?
C2 N1 C6 C5 -74.13(17) . . . . ?
C2 N1 C16 C21 -27.69(17) . . . . ?
C2 C13 C20 C22 1.0(3) . . . . ?
C2 C13 C21 C16 -15.7(2) . . . . ?
C2 C14 C18 C22 0.6(3) . . . . ?
C3 C4 C12 C9 -0.8(3) . . . . ?
C4 C3 C6 N1 94.24(17) . . . . ?
C4 C3 C6 C5 -31.92(19) . . . . ?
C4 C3 C10 C8 1.1(2) . . . . ?
C4 C3 C10 C15 -179.64(16) . . . . ?
C6 N1 C2 C13 158.09(13) . . . . ?
C6 N1 C2 C14 -24.2(2) . . . . ?
C6 N1 C16 C21 -168.00(14) . . . . ?
C6 C3 C4 C12 -178.79(15) . . . . ?
C6 C3 C10 C8 179.61(14) . . . . ?
C6 C3 C10 C15 -1.2(2) . . . . ?
O7 C9 C12 C4 -177.80(17) . . . . ?
C8 C9 C12 C4 1.2(3) . . . . ?
C9 C8 C10 C3 -0.7(2) . . . . ?
C9 C8 C10 C15 -179.95(16) . . . . ?
C10 C3 C4 C12 -0.4(2) . . . . ?
C10 C3 C6 N1 -84.14(16) . . . . ?
C10 C3 C6 C5 149.71(14) . . . . ?
C10 C8 C9 O7 178.64(15) . . . . ?
C10 C8 C9 C12 -0.4(2) . . . . ?
C13 C2 C14 C18 -0.4(3) . . . . ?
C13 C20 C22 C18 -0.8(3) . . . . ?
C14 C2 C13 C20 -0.4(3) . . . . ?
C14 C2 C13 C21 -179.17(15) . . . . ?
C14 C18 C22 C20 0.0(3) . . . . ?
C16 N1 C2 C13 18.71(17) . . . . ?
C16 N1 C2 C14 -163.62(16) . . . . ?
C16 N1 C6 C3 -64.27(17) . . . . ?
C16 N1 C6 C5 61.24(18) . . . . ?
C19 O7 C9 C8 179.79(17) . . . . ?
C19 O7 C9 C12 -1.2(3) . . . . ?
C20 C13 C21 C16 165.8(2) . . . . ?
C21 C13 C20 C22 179.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
