# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_20200787
_database_code_depnum_ccdc_archive 'CCDC 2077460'
loop_
_audit_author_name
_audit_author_address
'ming gong' University
_audit_update_record             
;
2021-04-14 deposited with the CCDC.	2021-12-07 downloaded from the CCDC.
;
_audit_creation_date             2020-07-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H13 N3'
_chemical_formula_sum            'C18 H13 N3'
_chemical_formula_weight         271.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H15N2
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   10.9525(3)
_cell_length_b                   12.9657(4)
_cell_length_c                   20.7069(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.542(3)
_cell_angle_gamma                90
_cell_volume                     2858.76(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2094
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7080
_cell_measurement_theta_min      5.3600
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.900
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5277
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.072
_diffrn_reflns_theta_max         67.072
_diffrn_reflns_theta_min         4.393
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00 -11.00   1.00    2.00    --  -33.50 -37.00 120.00   93
  2  ω   -101.00 -34.00   1.00    2.00    --  -33.50 178.00  90.00   67
  3  ω     51.00 100.00   1.00    2.00    --   36.47  19.00-180.00   49
  4  ω    -31.00   7.00   1.00    2.00    --   36.47 -57.00  60.00   38
  5  ω     59.00  85.00   1.00    2.00    --   36.47 178.00   0.00   26
  6  ω     63.00  90.00   1.00    2.00    --   36.47 178.00 -30.00   27
  7  ω     58.00 108.00   1.00    2.00    --   36.47 178.00  60.00   50
  8  ω     20.00  55.00   1.00    2.00    --   36.47 -57.00  60.00   35
  9  ω      6.00  38.00   1.00    2.00    --   36.47  19.00-180.00   32
 10  ω     54.00  81.00   1.00    5.00    --  108.00 -94.00   0.00   27
 11  ω     39.00 133.00   1.00    5.00    --  108.00 -30.00-180.00   94
 12  ω    103.00 141.00   1.00    5.00    --  108.00  61.00  30.00   38
 13  ω     39.00 101.00   1.00    5.00    --  108.00 -45.00  60.00   62
 14  ω     57.00 109.00   1.00    5.00    --  108.00 -94.00  90.00   52
 15  ω     89.00 173.00   1.00    5.00    --  108.00  45.00   0.00   84
 16  ω    122.00 148.00   1.00    5.00    --  108.00  45.00 -60.00   26
 17  ω    127.00 178.00   1.00    5.00    --  108.00 111.00  90.00   51
 18  ω    100.00 150.00   1.00    5.00    --  108.00 111.00-150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0299199000
_diffrn_orient_matrix_UB_12      -0.0113615000
_diffrn_orient_matrix_UB_13      0.0761446000
_diffrn_orient_matrix_UB_21      -0.1171140000
_diffrn_orient_matrix_UB_22      -0.0684518000
_diffrn_orient_matrix_UB_23      -0.0059173000
_diffrn_orient_matrix_UB_31      0.0795031000
_diffrn_orient_matrix_UB_32      -0.0964873000
_diffrn_orient_matrix_UB_33      -0.0047284000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2064
_reflns_number_total             2555
_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 (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         0.127
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2555
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.043
_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)+(0.0574P)²+0.7675P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1230
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C13(H13), C14(H14), C15(H15), C16(H16)
;
_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 0.36215(13) 0.65614(10) 0.46523(6) 0.0405(3) Uani 1 1 d . . . . .
N2 N 0.01384(14) 0.56916(14) 0.43160(8) 0.0588(4) Uani 1 1 d . . . . .
N3 N 0.24422(17) 0.30791(13) 0.42401(9) 0.0631(5) Uani 1 1 d . . . . .
C1 C 0.2552(2) 0.73387(18) 0.26579(10) 0.0643(6) Uani 1 1 d . . . . .
H1 H 0.2725 0.7998 0.2527 0.077 Uiso 1 1 calc R . . . .
C2 C 0.1840(2) 0.66814(19) 0.21971(10) 0.0682(6) Uani 1 1 d . . . . .
H2 H 0.1540 0.6900 0.1761 0.082 Uiso 1 1 calc R . . . .
C3 C 0.1574(2) 0.57062(19) 0.23796(9) 0.0636(6) Uani 1 1 d . . . . .
H3 H 0.1092 0.5261 0.2069 0.076 Uiso 1 1 calc R . . . .
C4 C 0.20253(18) 0.53919(16) 0.30264(8) 0.0534(5) Uani 1 1 d . . . . .
H4 H 0.1850 0.4729 0.3150 0.064 Uiso 1 1 calc R . . . .
C5 C 0.27398(15) 0.60497(13) 0.34974(7) 0.0404(4) Uani 1 1 d . . . . .
C6 C 0.30221(17) 0.70382(14) 0.33178(9) 0.0476(4) Uani 1 1 d . . . . .
C7 C 0.3785(2) 0.77853(15) 0.38107(10) 0.0564(5) Uani 1 1 d . . . . .
H7A H 0.3230 0.8313 0.3912 0.068 Uiso 1 1 calc R . . . .
H7B H 0.4392 0.8122 0.3608 0.068 Uiso 1 1 calc R . . . .
C8 C 0.44742(16) 0.72822(13) 0.44528(8) 0.0458(4) Uani 1 1 d . . . . .
H8A H 0.5212 0.6923 0.4387 0.055 Uiso 1 1 calc R . . . .
H8B H 0.4741 0.7801 0.4794 0.055 Uiso 1 1 calc R . . . .
C9 C 0.32865(14) 0.56905(12) 0.41983(7) 0.0362(4) Uani 1 1 d . . . . .
H9 H 0.4055 0.5303 0.4200 0.043 Uiso 1 1 calc R . . . .
C10 C 0.24610(14) 0.50261(12) 0.45651(7) 0.0367(4) Uani 1 1 d . . . . .
C11 C 0.31400(14) 0.52446(12) 0.52886(7) 0.0370(4) Uani 1 1 d . . . . .
C12 C 0.37948(14) 0.61673(12) 0.52941(7) 0.0385(4) Uani 1 1 d . . . . .
C13 C 0.44717(16) 0.65760(14) 0.58906(8) 0.0467(4) Uani 1 1 d . . . . .
H13 H 0.4909 0.7193 0.5903 0.056 Uiso 1 1 calc R . . . .
C14 C 0.44721(17) 0.60310(16) 0.64658(8) 0.0530(5) Uani 1 1 d . . . . .
H14 H 0.4923 0.6290 0.6870 0.064 Uiso 1 1 calc R . . . .
C15 C 0.38264(17) 0.51168(16) 0.64582(8) 0.0527(5) Uani 1 1 d . . . . .
H15 H 0.3855 0.4768 0.6854 0.063 Uiso 1 1 calc R . . . .
C16 C 0.31306(16) 0.47105(14) 0.58619(8) 0.0451(4) Uani 1 1 d . . . . .
H16 H 0.2677 0.4102 0.5852 0.054 Uiso 1 1 calc R . . . .
C17 C 0.11435(16) 0.54010(13) 0.44210(8) 0.0418(4) Uani 1 1 d . . . . .
C18 C 0.24476(16) 0.39230(13) 0.43834(8) 0.0434(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C8 1.448(2) . ?
N1 C9 1.4601(19) . ?
N1 C12 1.395(2) . ?
N2 C17 1.135(2) . ?
N3 C18 1.133(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.377(3) . ?
C1 C6 1.398(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.371(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.391(2) . ?
C5 C6 1.389(2) . ?
C5 C9 1.508(2) . ?
C6 C7 1.509(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.514(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9 0.9800 . ?
C9 C10 1.568(2) . ?
C10 C11 1.535(2) . ?
C10 C17 1.485(2) . ?
C10 C18 1.478(2) . ?
C11 C12 1.394(2) . ?
C11 C16 1.376(2) . ?
C12 C13 1.388(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.385(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.394(2) . ?
C16 H16 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
C8 N1 C9 113.39(13) . . ?
C12 N1 C8 123.74(13) . . ?
C12 N1 C9 106.72(13) . . ?
C2 C1 H1 119.2 . . ?
C2 C1 C6 121.6(2) . . ?
C6 C1 H1 119.2 . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.18(18) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.4(2) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.06(19) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C9 121.13(16) . . ?
C6 C5 C4 120.13(16) . . ?
C6 C5 C9 118.64(15) . . ?
C1 C6 C7 120.05(18) . . ?
C5 C6 C1 117.69(18) . . ?
C5 C6 C7 122.24(15) . . ?
C6 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
C6 C7 C8 113.61(15) . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
N1 C8 C7 107.83(14) . . ?
N1 C8 H8A 110.1 . . ?
N1 C8 H8B 110.1 . . ?
C7 C8 H8A 110.1 . . ?
C7 C8 H8B 110.1 . . ?
H8A C8 H8B 108.5 . . ?
N1 C9 C5 111.35(13) . . ?
N1 C9 H9 108.0 . . ?
N1 C9 C10 101.51(12) . . ?
C5 C9 H9 108.0 . . ?
C5 C9 C10 119.46(13) . . ?
C10 C9 H9 108.0 . . ?
C11 C10 C9 99.72(12) . . ?
C17 C10 C9 111.48(13) . . ?
C17 C10 C11 111.20(13) . . ?
C18 C10 C9 112.38(13) . . ?
C18 C10 C11 113.62(13) . . ?
C18 C10 C17 108.32(13) . . ?
C12 C11 C10 107.29(13) . . ?
C16 C11 C10 130.48(15) . . ?
C16 C11 C12 122.19(15) . . ?
C11 C12 N1 110.60(13) . . ?
C13 C12 N1 129.28(16) . . ?
C13 C12 C11 120.10(15) . . ?
C12 C13 H13 121.2 . . ?
C14 C13 C12 117.59(17) . . ?
C14 C13 H13 121.2 . . ?
C13 C14 H14 118.9 . . ?
C15 C14 C13 122.14(16) . . ?
C15 C14 H14 118.9 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.53(17) . . ?
C16 C15 H15 119.7 . . ?
C11 C16 C15 117.45(17) . . ?
C11 C16 H16 121.3 . . ?
C15 C16 H16 121.3 . . ?
N2 C17 C10 179.4(2) . . ?
N3 C18 C10 179.4(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 C9 C10 C11 -34.48(14) . . . . ?
N1 C9 C10 C17 83.01(14) . . . . ?
N1 C9 C10 C18 -155.16(13) . . . . ?
N1 C12 C13 C14 178.79(17) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C1 C6 C7 C8 -166.54(18) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
C2 C1 C6 C7 -179.2(2) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C3 C4 C5 C9 -177.09(17) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C4 C5 C6 C7 179.49(17) . . . . ?
C4 C5 C9 N1 -160.83(15) . . . . ?
C4 C5 C9 C10 -43.0(2) . . . . ?
C5 C6 C7 C8 14.7(3) . . . . ?
C5 C9 C10 C11 -157.28(14) . . . . ?
C5 C9 C10 C17 -39.78(19) . . . . ?
C5 C9 C10 C18 82.04(17) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C6 C5 C9 N1 22.8(2) . . . . ?
C6 C5 C9 C10 140.61(15) . . . . ?
C6 C7 C8 N1 -43.2(2) . . . . ?
C8 N1 C9 C5 -55.75(17) . . . . ?
C8 N1 C9 C10 176.05(13) . . . . ?
C8 N1 C12 C11 -157.92(15) . . . . ?
C8 N1 C12 C13 23.6(3) . . . . ?
C9 N1 C8 C7 66.23(19) . . . . ?
C9 N1 C12 C11 -23.57(18) . . . . ?
C9 N1 C12 C13 157.97(17) . . . . ?
C9 C5 C6 C1 177.16(16) . . . . ?
C9 C5 C6 C7 -4.1(2) . . . . ?
C9 C10 C11 C12 22.09(15) . . . . ?
C9 C10 C11 C16 -160.39(17) . . . . ?
C10 C11 C12 N1 -0.59(18) . . . . ?
C10 C11 C12 C13 178.04(14) . . . . ?
C10 C11 C16 C15 -178.35(16) . . . . ?
C11 C12 C13 C14 0.5(2) . . . . ?
C12 N1 C8 C7 -162.02(15) . . . . ?
C12 N1 C9 C5 164.63(13) . . . . ?
C12 N1 C9 C10 36.43(15) . . . . ?
C12 C11 C16 C15 -1.2(3) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 -0.7(3) . . . . ?
C14 C15 C16 C11 1.3(3) . . . . ?
C16 C11 C12 N1 -178.36(15) . . . . ?
C16 C11 C12 C13 0.3(2) . . . . ?
C17 C10 C11 C12 -95.61(15) . . . . ?
C17 C10 C11 C16 81.9(2) . . . . ?
C18 C10 C11 C12 141.87(14) . . . . ?
C18 C10 C11 C16 -40.6(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 1.142
_oxdiff_exptl_absorpt_empirical_full_min 0.845
####################################################################### 
# 
# 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_202012308
_database_code_depnum_ccdc_archive 'CCDC 2077465'
loop_
_audit_author_name
_audit_author_address
'ming gong' University
_audit_update_record             
;
2021-04-14 deposited with the CCDC.	2021-12-07 downloaded from the CCDC.
;
_audit_creation_date             2020-12-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H15 Br N2 O2'
_chemical_formula_sum            'C19 H15 Br N2 O2'
_chemical_formula_weight         383.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O3N2Br1
_chemical_oxdiff_usercomment     r
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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                   8.5331(6)
_cell_length_b                   9.1322(6)
_cell_length_c                   11.9513(10)
_cell_angle_alpha                77.749(6)
_cell_angle_beta                 79.907(7)
_cell_angle_gamma                65.413(7)
_cell_volume                     823.62(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3198
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6930
_cell_measurement_theta_min      3.7860
_shelx_estimated_absorpt_T_max   0.720
_shelx_estimated_absorpt_T_min   0.621
_exptl_absorpt_coefficient_mu    3.514
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.15
_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  0.0433
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11170
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         3.803
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -3.00  25.00   1.00    1.00    --    0.00  57.00 120.00   28
  2  ω    -39.00  14.00   1.00    1.00    --    0.00 -57.00 -90.00   53
  3  ω    -52.00  -5.00   1.00    1.00    --  -33.50 -77.00 120.00   47
  4  ω   -101.00 -75.00   1.00    1.00    --  -33.50 -77.00 120.00   26
  5  ω    -34.00  -8.00   1.00    1.00    --  -33.50 -77.00-120.00   26
  6  ω    -82.00 -52.00   1.00    1.00    --  -33.50 -77.00-120.00   30
  7  ω     18.00  48.00   1.00    1.00    --   36.47 -57.00 120.00   30
  8  ω     -2.00  66.00   1.00    1.00    --   36.47 -99.00-120.00   68
  9  ω    -21.00   8.00   1.00    1.00    --   36.47 -57.00 120.00   29
 10  ω     23.00  74.00   1.00    1.00    --   36.47 -99.00 -90.00   51
 11  ω    -13.00  46.00   1.00    1.00    --   36.47 -77.00 -30.00   59
 12  ω     72.00 106.00   1.00    1.00    --   36.47 178.00-150.00   34
 13  ω      5.00  73.00   1.00    1.00    --   36.47 -99.00  60.00   68
 14  ω      7.00  32.00   1.00    1.00    --   44.00  92.00-114.94   25
 15  ω     16.00  41.00   1.00    1.00    --   48.00  83.00  -0.60   25
 16  ω     13.00  38.00   1.00    1.00    --   48.00  88.00  90.26   25
 17  ω     16.00  42.00   1.00    1.00    --   48.00  83.00-138.42   26
 18  ω     15.00  40.00   1.00    1.00    --   48.00  85.00 150.69   25
 19  ω     13.00  38.00   1.00    1.00    --   48.00  88.00  20.98   25
 20  ω     20.00  45.00   1.00    1.00    --   52.00  83.00 -84.39   25
 21  ω     20.00  45.00   1.00    1.00    --   52.00  84.00  54.03   25
 22  ω     30.00 122.00   1.00    1.00    --   56.00  77.00-173.41   92
 23  ω    100.00 125.00   1.00    1.00    --   56.00  77.00 104.21   25
 24  ω     30.00  71.00   1.00    1.00    --   56.00  79.00 -47.44   41
 25  ω     27.00  63.00   1.00    1.00    --   56.00  77.00 104.21   36
 26  ω     33.00  58.00   1.00    1.00    --   56.00  73.00-113.33   25
 27  ω     76.00 124.00   1.00    1.00    --   56.00  79.00 -47.44   48
 28  ω     87.00 124.00   1.00    1.00    --   56.00  73.00-113.33   37
 29  ω     29.00 125.00   1.00    1.00    --   56.00  76.00  11.37   96
 30  ω     34.00  69.00   1.00    1.00    --   60.00  73.00 149.16   35
 31  ω     32.00  74.00   1.00    1.00    --   60.00  75.00  71.39   42
 32  ω     90.00 128.00   1.00    1.00    --   60.00  75.00  71.39   38
 33  ω     35.00  74.00   1.00    1.00    --   60.00  72.00 -78.56   39
 34  ω     83.00 109.00   1.00    1.00    --   60.00  73.00 149.16   26
 35  ω     48.00  91.00   1.00    1.00    --   68.00  62.00 151.05   43
 36  ω    136.00 176.00   1.00    1.50    --  108.00  61.00 120.00   40
 37  ω     79.00 170.00   1.00    1.50    --  108.00  77.00  90.00   91
 38  ω     88.00 114.00   1.00    1.50    --  108.00  61.00 120.00   26
 39  ω     89.00 123.00   1.00    1.50    --  108.00  45.00 150.00   34
 40  ω     41.00 126.00   1.00    1.50    --  108.00 -61.00   0.00   85
 41  ω    121.00 147.00   1.00    1.50    --  108.00 178.00 150.00   26
 42  ω     88.00 130.00   1.00    1.50    --  108.00  61.00  60.00   42
 43  ω     79.00 105.00   1.00    1.50    --  108.00  77.00 -30.00   26
 44  ω     69.00  96.00   1.00    1.50    --  108.00 178.00 150.00   27
 45  ω     88.00 118.00   1.00    1.50    --  108.00  61.00 -30.00   30
 46  ω     88.00 157.00   1.00    1.50    --  108.00  61.00-180.00   69
 47  ω    116.00 174.00   1.00    1.50    --  108.00  77.00  60.00   58
 48  ω     80.00 106.00   1.00    1.50    --  108.00  77.00  60.00   26
 49  ω     81.00 107.00   1.00    1.50    --  108.00  77.00-120.00   26
 50  ω    120.00 171.00   1.00    1.50    --  108.00  77.00 -90.00   51
 51  ω    125.00 162.00   1.00    1.50    --  108.00  61.00 -30.00   37
 52  ω     81.00 107.00   1.00    1.50    --  108.00  77.00-150.00   26
 53  ω     80.00 106.00   1.00    1.50    --  108.00  77.00 -90.00   26
 54  ω     90.00 129.00   1.00    1.50    --  108.00  61.00 -90.00   39
 55  ω     53.00 110.00   1.00    1.50    --  108.00 -94.00 120.00   57
 56  ω     79.00 105.00   1.00    1.50    --  108.00  77.00  30.00   26
 57  ω     79.00 105.00   1.00    1.50    --  108.00  77.00 -60.00   26
 58  ω    116.00 177.00   1.00    1.50    --  108.00  77.00 -60.00   61
 59  ω     79.00 105.00   1.00    1.50    --  108.00  77.00   0.00   26
 60  ω     89.00 171.00   1.00    1.50    --  108.00  61.00-150.00   82
 61  ω     39.00  98.00   1.00    1.50    --  108.00 -94.00-150.00   59
 62  ω     53.00 110.00   1.00    1.50    --  108.00-111.00   0.00   57
 63  ω    123.00 168.00   1.00    1.50    --  108.00  77.00 150.00   45
 64  ω     79.00 105.00   1.00    1.50    --  108.00  77.00-180.00   26
 65  ω     79.00 117.00   1.00    1.50    --  108.00  77.00 150.00   38
 66  ω     88.00 176.00   1.00    1.50    --  108.00  61.00   0.00   88
 67  ω     90.00 116.00   1.00    1.50    --  108.00  61.00 -60.00   26
 68  ω     41.00  96.00   1.00    1.50    --  108.00 -94.00 -90.00   55
 69  ω     91.00 170.00   1.00    1.50    --  108.00  61.00  30.00   79
 70  ω     89.00 164.00   1.00    1.50    --  108.00  61.00-120.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0239514000
_diffrn_orient_matrix_UB_12      0.1534224000
_diffrn_orient_matrix_UB_13      -0.0689682000
_diffrn_orient_matrix_UB_21      -0.1968917000
_diffrn_orient_matrix_UB_22      0.0865054000
_diffrn_orient_matrix_UB_23      -0.0075430000
_diffrn_orient_matrix_UB_31      -0.0214373000
_diffrn_orient_matrix_UB_32      0.0651808000
_diffrn_orient_matrix_UB_33      0.1129351000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2418
_reflns_number_total             2930
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2930
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.041
_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)+(0.0326P)²+0.5982P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0907
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.14472(5) 0.28921(5) 0.39231(3) 0.06018(15) Uani 1 1 d . . . . .
O1 O 0.5706(4) 0.4785(3) 0.6682(3) 0.0834(9) Uani 1 1 d . . . . .
O2 O 0.4853(3) 0.2737(3) 0.7066(2) 0.0611(7) Uani 1 1 d . . . . .
N1 N 0.8723(3) -0.0272(3) 0.8883(2) 0.0421(6) Uani 1 1 d . . . . .
N2 N 0.9145(4) 0.3928(4) 0.8166(3) 0.0575(7) Uani 1 1 d . . . . .
C1 C 0.9919(4) 0.1546(4) 0.5947(2) 0.0402(7) Uani 1 1 d . . . . .
H1 H 0.8960 0.2521 0.5825 0.048 Uiso 1 1 calc R . . . .
C2 C 1.1381(4) 0.1241(4) 0.5178(3) 0.0431(7) Uani 1 1 d . . . . .
C3 C 1.2798(4) -0.0207(4) 0.5332(3) 0.0495(8) Uani 1 1 d . . . . .
H3 H 1.3775 -0.0411 0.4803 0.059 Uiso 1 1 calc R . . . .
C4 C 1.2751(4) -0.1347(4) 0.6277(3) 0.0498(8) Uani 1 1 d . . . . .
H4 H 1.3707 -0.2330 0.6379 0.060 Uiso 1 1 calc R . . . .
C5 C 1.1306(4) -0.1075(4) 0.7094(3) 0.0393(7) Uani 1 1 d . . . . .
C6 C 0.9882(4) 0.0388(3) 0.6909(2) 0.0359(6) Uani 1 1 d . . . . .
C7 C 0.8290(4) 0.0659(3) 0.7746(2) 0.0354(6) Uani 1 1 d . . . . .
H7 H 0.7536 0.0280 0.7462 0.043 Uiso 1 1 calc R . . . .
C8 C 0.7177(4) 0.2427(3) 0.8023(2) 0.0370(6) Uani 1 1 d . . . . .
C9 C 0.6367(4) 0.2030(4) 0.9236(2) 0.0379(6) Uani 1 1 d . . . . .
C10 C 0.7346(4) 0.0423(4) 0.9673(2) 0.0383(6) Uani 1 1 d . . . . .
C11 C 0.6917(4) -0.0232(4) 1.0788(3) 0.0455(7) Uani 1 1 d . . . . .
H11 H 0.7542 -0.1310 1.1092 0.055 Uiso 1 1 calc R . . . .
C12 C 0.5524(4) 0.0780(4) 1.1427(3) 0.0492(8) Uani 1 1 d . . . . .
H12 H 0.5220 0.0359 1.2173 0.059 Uiso 1 1 calc R . . . .
C13 C 0.4553(4) 0.2408(4) 1.1003(3) 0.0485(8) Uani 1 1 d . . . . .
H13 H 0.3634 0.3058 1.1459 0.058 Uiso 1 1 calc R . . . .
C14 C 0.4995(4) 0.3033(4) 0.9882(3) 0.0437(7) Uani 1 1 d . . . . .
H14 H 0.4373 0.4110 0.9574 0.052 Uiso 1 1 calc R . . . .
C15 C 1.1354(4) -0.2333(4) 0.8158(3) 0.0470(8) Uani 1 1 d . . . . .
H15A H 1.1757 -0.3393 0.7922 0.056 Uiso 1 1 calc R . . . .
H15B H 1.2192 -0.2377 0.8632 0.056 Uiso 1 1 calc R . . . .
C16 C 0.9635(4) -0.2016(4) 0.8885(3) 0.0454(7) Uani 1 1 d . . . . .
H16A H 0.8948 -0.2425 0.8573 0.054 Uiso 1 1 calc R . . . .
H16B H 0.9828 -0.2575 0.9666 0.054 Uiso 1 1 calc R . . . .
C17 C 0.8297(4) 0.3295(4) 0.8077(3) 0.0415(7) Uani 1 1 d . . . . .
C18 C 0.5828(4) 0.3477(4) 0.7175(3) 0.0424(7) Uani 1 1 d . . . . .
C19 C 0.3466(5) 0.3620(5) 0.6323(4) 0.0706(11) Uani 1 1 d . . . . .
H19A H 0.3951 0.3775 0.5542 0.106 Uiso 1 1 calc GR . . . .
H19B H 0.2762 0.4662 0.6557 0.106 Uiso 1 1 calc GR . . . .
H19C H 0.2766 0.3007 0.6381 0.106 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
Br1 C2 1.900(3) . ?
O1 C18 1.185(4) . ?
O2 C18 1.307(4) . ?
O2 C19 1.452(4) . ?
N1 C7 1.459(3) . ?
N1 C10 1.386(4) . ?
N1 C16 1.453(4) . ?
N2 C17 1.126(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.376(4) . ?
C1 C6 1.393(4) . ?
C2 C3 1.375(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.372(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.400(4) . ?
C5 C6 1.389(4) . ?
C5 C15 1.516(4) . ?
C6 C7 1.501(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.568(4) . ?
C8 C9 1.531(4) . ?
C8 C17 1.491(4) . ?
C8 C18 1.532(4) . ?
C9 C10 1.390(4) . ?
C9 C14 1.377(4) . ?
C10 C11 1.393(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.398(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.393(4) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.515(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C18 O2 C19 117.3(3) . . ?
C10 N1 C7 107.8(2) . . ?
C10 N1 C16 124.1(2) . . ?
C16 N1 C7 113.7(2) . . ?
C2 C1 H1 120.1 . . ?
C2 C1 C6 119.8(3) . . ?
C6 C1 H1 120.1 . . ?
C1 C2 Br1 118.9(2) . . ?
C3 C2 Br1 120.1(2) . . ?
C3 C2 C1 121.0(3) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 119.0 . . ?
C3 C4 C5 122.0(3) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 C15 120.0(3) . . ?
C6 C5 C4 117.9(3) . . ?
C6 C5 C15 122.1(3) . . ?
C1 C6 C7 121.2(3) . . ?
C5 C6 C1 120.4(3) . . ?
C5 C6 C7 118.4(2) . . ?
N1 C7 C6 111.3(2) . . ?
N1 C7 H7 108.1 . . ?
N1 C7 C8 102.3(2) . . ?
C6 C7 H7 108.1 . . ?
C6 C7 C8 118.6(2) . . ?
C8 C7 H7 108.1 . . ?
C9 C8 C7 100.1(2) . . ?
C9 C8 C18 113.1(2) . . ?
C17 C8 C7 111.2(2) . . ?
C17 C8 C9 109.2(2) . . ?
C17 C8 C18 109.1(2) . . ?
C18 C8 C7 114.0(2) . . ?
C10 C9 C8 108.2(2) . . ?
C14 C9 C8 129.5(3) . . ?
C14 C9 C10 122.1(3) . . ?
N1 C10 C9 110.5(2) . . ?
N1 C10 C11 129.6(3) . . ?
C9 C10 C11 119.9(3) . . ?
C10 C11 H11 121.2 . . ?
C12 C11 C10 117.6(3) . . ?
C12 C11 H11 121.2 . . ?
C11 C12 H12 118.5 . . ?
C11 C12 C13 123.0(3) . . ?
C13 C12 H12 118.5 . . ?
C12 C13 H13 120.8 . . ?
C14 C13 C12 118.5(3) . . ?
C14 C13 H13 120.8 . . ?
C9 C14 C13 119.0(3) . . ?
C9 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C5 C15 H15A 108.6 . . ?
C5 C15 H15B 108.6 . . ?
H15A C15 H15B 107.5 . . ?
C16 C15 C5 114.8(2) . . ?
C16 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
N1 C16 C15 108.8(2) . . ?
N1 C16 H16A 109.9 . . ?
N1 C16 H16B 109.9 . . ?
C15 C16 H16A 109.9 . . ?
C15 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
N2 C17 C8 177.2(3) . . ?
O1 C18 O2 125.0(3) . . ?
O1 C18 C8 123.8(3) . . ?
O2 C18 C8 111.3(2) . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
Br1 C2 C3 C4 176.7(2) . . . . ?
N1 C7 C8 C9 -30.2(3) . . . . ?
N1 C7 C8 C17 85.1(3) . . . . ?
N1 C7 C8 C18 -151.2(2) . . . . ?
N1 C10 C11 C12 175.4(3) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C1 C6 C7 N1 -155.1(3) . . . . ?
C1 C6 C7 C8 -36.9(4) . . . . ?
C2 C1 C6 C5 -0.4(4) . . . . ?
C2 C1 C6 C7 -178.1(3) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C3 C4 C5 C6 1.3(5) . . . . ?
C3 C4 C5 C15 -176.6(3) . . . . ?
C4 C5 C6 C1 -0.9(4) . . . . ?
C4 C5 C6 C7 176.9(3) . . . . ?
C4 C5 C15 C16 -171.5(3) . . . . ?
C5 C6 C7 N1 27.1(4) . . . . ?
C5 C6 C7 C8 145.3(3) . . . . ?
C5 C15 C16 N1 -37.3(4) . . . . ?
C6 C1 C2 Br1 -176.3(2) . . . . ?
C6 C1 C2 C3 1.3(5) . . . . ?
C6 C5 C15 C16 10.7(4) . . . . ?
C6 C7 C8 C9 -153.0(2) . . . . ?
C6 C7 C8 C17 -37.8(3) . . . . ?
C6 C7 C8 C18 86.0(3) . . . . ?
C7 N1 C10 C9 -22.0(3) . . . . ?
C7 N1 C10 C11 161.1(3) . . . . ?
C7 N1 C16 C15 62.8(3) . . . . ?
C7 C8 C9 C10 18.7(3) . . . . ?
C7 C8 C9 C14 -165.7(3) . . . . ?
C7 C8 C18 O1 -126.8(4) . . . . ?
C7 C8 C18 O2 52.8(3) . . . . ?
C8 C9 C10 N1 0.7(3) . . . . ?
C8 C9 C10 C11 177.9(3) . . . . ?
C8 C9 C14 C13 -176.3(3) . . . . ?
C9 C8 C18 O1 119.8(4) . . . . ?
C9 C8 C18 O2 -60.6(3) . . . . ?
C9 C10 C11 C12 -1.2(4) . . . . ?
C10 N1 C7 C6 160.5(2) . . . . ?
C10 N1 C7 C8 32.9(3) . . . . ?
C10 N1 C16 C15 -162.8(3) . . . . ?
C10 C9 C14 C13 -1.2(5) . . . . ?
C10 C11 C12 C13 -0.2(5) . . . . ?
C11 C12 C13 C14 0.8(5) . . . . ?
C12 C13 C14 C9 -0.1(5) . . . . ?
C14 C9 C10 N1 -175.3(3) . . . . ?
C14 C9 C10 C11 1.9(5) . . . . ?
C15 C5 C6 C1 176.9(3) . . . . ?
C15 C5 C6 C7 -5.3(4) . . . . ?
C16 N1 C7 C6 -57.9(3) . . . . ?
C16 N1 C7 C8 174.5(2) . . . . ?
C16 N1 C10 C9 -158.6(3) . . . . ?
C16 N1 C10 C11 24.6(5) . . . . ?
C17 C8 C9 C10 -98.1(3) . . . . ?
C17 C8 C9 C14 77.5(4) . . . . ?
C17 C8 C18 O1 -1.9(5) . . . . ?
C17 C8 C18 O2 177.7(3) . . . . ?
C18 C8 C9 C10 140.3(3) . . . . ?
C18 C8 C9 C14 -44.1(4) . . . . ?
C19 O2 C18 O1 -3.0(5) . . . . ?
C19 O2 C18 C8 177.5(3) . . . . ?

_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 1.613
_oxdiff_exptl_absorpt_empirical_full_min 0.818
####################################################################### 
# 
# 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_202011277
_database_code_depnum_ccdc_archive 'CCDC 2077464'
loop_
_audit_author_name
_audit_author_address
'ming gong'
;University
China
;
_audit_update_record             
;
2021-04-14 deposited with the CCDC.	2021-12-07 downloaded from the CCDC.
;
_audit_creation_date             2020-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H15 N3 O'
_chemical_formula_sum            'C19 H15 N3 O'
_chemical_formula_weight         301.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         C30H3O3N2
_chemical_oxdiff_usercomment     r
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   7.5372(7)
_cell_length_b                   7.8330(5)
_cell_length_c                   13.1572(11)
_cell_angle_alpha                81.704(6)
_cell_angle_beta                 86.697(7)
_cell_angle_gamma                83.076(6)
_cell_volume                     762.42(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1651
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.2770
_cell_measurement_theta_min      5.7350
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.884
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94947
_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            'blackish colourless'
_exptl_crystal_colour_modifier   blackish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5367
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.046
_diffrn_reflns_theta_max         67.046
_diffrn_reflns_theta_min         3.397
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  35.00   1.00    1.00    --  -33.50  57.00  30.00   87
  2  ω    -71.00  39.00   1.00    1.00    --  -33.50  19.00 -30.00  110
  3  ω     57.00 110.00   1.00    1.00    --   36.47 178.00 -60.00   53
  4  ω     24.00  98.00   1.00    1.00    --   36.47-135.00  -0.00   74
  5  ω      8.00 106.00   1.00    1.00    --   36.47  77.00 150.00   98
  6  ω     57.00 110.00   1.00    1.00    --   36.47 178.00-180.00   53
  7  ω     57.00 110.00   1.00    1.00    --   36.47 178.00  30.00   53
  8  ω     18.00 105.00   1.00    1.00    --   36.47  57.00-180.00   87
  9  ω     57.00 110.00   1.00    1.00    --   36.47 178.00 150.00   53
 10  ω     57.00 110.00   1.00    1.00    --   36.47 178.00  90.00   53
 11  ω    -32.00  55.00   1.00    1.00    --   36.47 -57.00  90.00   87
 12  ω     38.00 124.00   1.00    1.00    --  108.00-134.00 178.00   86
 13  ω    104.00 178.00   1.00    1.00    --  108.00 111.00  30.00   74
 14  ω     79.00 108.00   1.00    1.00    --  108.00-111.00 -30.00   29
 15  ω     38.00  63.00   1.00    1.00    --  108.00-111.00 -30.00   25
 16  ω     50.00 119.00   1.00    1.00    --  108.00 -61.00  90.00   69
 17  ω     91.00 136.00   1.00    1.00    --  108.00 -77.00 -30.00   45
 18  ω    141.00 173.00   1.00    1.00    --  108.00  45.00 120.00   32
 19  ω     93.00 127.00   1.00    1.00    --  108.00  45.00 120.00   34
 20  ω    109.00 135.00   1.00    1.00    --  108.00 -15.00 150.00   26
 21  ω     40.00  75.00   1.00    1.00    --  108.00 -15.00 150.00   35
 22  ω     90.00 115.00   1.00    1.00    --  108.00  45.00-150.00   25
 23  ω    139.00 172.00   1.00    1.00    --  108.00  45.00-150.00   33
 24  ω     44.00 121.00   1.00    1.00    --  108.00 -45.00 -60.00   77
 25  ω     89.00 157.00   1.00    1.00    --  108.00  61.00  90.00   68
 26  ω     38.00  68.00   1.00    1.00    --  108.00 -94.00 -30.00   30
 27  ω     73.00 110.00   1.00    1.00    --  108.00 -94.00 -30.00   37
 28  ω     82.00 171.00   1.00    1.00    --  108.00  30.00-180.00   89
 29  ω     92.00 150.00   1.00    1.00    --  108.00 178.00 -30.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1173735000
_diffrn_orient_matrix_UB_12      0.0015659000
_diffrn_orient_matrix_UB_13      -0.0998668000
_diffrn_orient_matrix_UB_21      -0.1686706000
_diffrn_orient_matrix_UB_22      0.0466539000
_diffrn_orient_matrix_UB_23      -0.0636452000
_diffrn_orient_matrix_UB_31      0.0154307000
_diffrn_orient_matrix_UB_32      0.1945284000
_diffrn_orient_matrix_UB_33      -0.0008103000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2010
_reflns_number_total             2719
_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         0.126
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2719
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.061
_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)+(0.0503P)²+0.0612P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1220
_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:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14)
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
C1 C 0.2506(3) 0.9784(3) 0.04602(16) 0.0547(5) Uani 1 1 d . . . . .
C2 C 0.2198(3) 1.1364(3) -0.01786(17) 0.0678(6) Uani 1 1 d . . . . .
H2 H 0.2149 1.1393 -0.0886 0.081 Uiso 1 1 calc R . . . .
C3 C 0.1967(3) 1.2889(3) 0.0255(2) 0.0766(7) Uani 1 1 d . . . . .
H3 H 0.1776 1.3934 -0.0181 0.092 Uiso 1 1 calc R . . . .
C4 C 0.2004(3) 1.2943(3) 0.12936(18) 0.0668(6) Uani 1 1 d . . . . .
H4 H 0.1823 1.3990 0.1561 0.080 Uiso 1 1 calc R . . . .
C5 C 0.2324(2) 1.1367(2) 0.19278(16) 0.0517(5) Uani 1 1 d . . . . .
C6 C 0.2601(2) 0.9829(2) 0.15041(15) 0.0481(5) Uani 1 1 d . . . . .
C7 C 0.2833(2) 0.8322(2) 0.23746(14) 0.0443(4) Uani 1 1 d . . . . .
C8 C 0.3328(2) 0.9302(2) 0.32552(15) 0.0466(5) Uani 1 1 d . . . . .
H8 H 0.4609 0.9424 0.3174 0.056 Uiso 1 1 calc R . . . .
C9 C 0.2938(2) 0.8573(2) 0.43569(14) 0.0443(4) Uani 1 1 d . . . . .
C10 C 0.2439(2) 0.9736(2) 0.50636(15) 0.0481(5) Uani 1 1 d . . . . .
C11 C 0.2082(3) 0.9065(3) 0.60811(16) 0.0572(5) Uani 1 1 d . . . . .
H11 H 0.1754 0.9824 0.6560 0.069 Uiso 1 1 calc R . . . .
C12 C 0.2204(3) 0.7302(3) 0.63970(15) 0.0580(5) Uani 1 1 d . . . . .
H12 H 0.1946 0.6882 0.7081 0.070 Uiso 1 1 calc R . . . .
C13 C 0.2707(3) 0.6163(2) 0.57001(15) 0.0548(5) Uani 1 1 d . . . . .
H13 H 0.2791 0.4972 0.5911 0.066 Uiso 1 1 calc R . . . .
C14 C 0.3085(2) 0.6798(2) 0.46890(15) 0.0499(5) Uani 1 1 d . . . . .
H14 H 0.3445 0.6027 0.4222 0.060 Uiso 1 1 calc R . . . .
C15 C 0.2750(3) 1.2278(2) 0.36418(17) 0.0621(6) Uani 1 1 d . . . . .
H15A H 0.2107 1.3405 0.3414 0.075 Uiso 1 1 calc R . . . .
H15B H 0.4020 1.2392 0.3586 0.075 Uiso 1 1 calc R . . . .
C16 C 0.2205(3) 1.1680(2) 0.47485(16) 0.0587(5) Uani 1 1 d . . . . .
H16A H 0.2901 1.2206 0.5191 0.070 Uiso 1 1 calc R . . . .
H16B H 0.0957 1.2105 0.4864 0.070 Uiso 1 1 calc R . . . .
C17 C 0.4260(3) 0.6934(2) 0.21687(14) 0.0506(5) Uani 1 1 d . . . . .
C18 C 0.1119(3) 0.7558(2) 0.25976(14) 0.0488(5) Uani 1 1 d . . . . .
C19 C 0.2786(3) 0.8075(3) -0.09127(16) 0.0786(7) Uani 1 1 d . . . . .
H19A H 0.3695 0.8737 -0.1253 0.118 Uiso 1 1 calc GR . . . .
H19B H 0.1647 0.8531 -0.1190 0.118 Uiso 1 1 calc GR . . . .
H19C H 0.3056 0.6883 -0.1019 0.118 Uiso 1 1 calc GR . . . .
N1 N 0.5371(3) 0.5867(2) 0.20323(14) 0.0708(5) Uani 1 1 d . . . . .
N2 N -0.0207(2) 0.7010(2) 0.27467(15) 0.0719(5) Uani 1 1 d . . . . .
N3 N 0.2349(2) 1.10235(17) 0.29948(13) 0.0509(4) Uani 1 1 d . . . . .
O1 O 0.2726(2) 0.81868(18) 0.01620(10) 0.0646(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.395(3) . ?
C1 C6 1.385(3) . ?
C1 O1 1.353(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(3) . ?
C5 C6 1.387(2) . ?
C5 N3 1.392(2) . ?
C6 C7 1.523(2) . ?
C7 C8 1.564(2) . ?
C7 C17 1.477(2) . ?
C7 C18 1.485(2) . ?
C8 H8 0.9800 . ?
C8 C9 1.505(2) . ?
C8 N3 1.462(2) . ?
C9 C10 1.399(2) . ?
C9 C14 1.389(2) . ?
C10 C11 1.389(3) . ?
C10 C16 1.511(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.377(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.377(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.378(3) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.513(3) . ?
C15 N3 1.458(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N1 1.136(2) . ?
C18 N2 1.131(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C19 O1 1.427(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 117.7(2) . . ?
O1 C1 C2 126.4(2) . . ?
O1 C1 C6 115.95(17) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.1(2) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 118.2 . . ?
C4 C3 C2 123.6(2) . . ?
C4 C3 H3 118.2 . . ?
C3 C4 H4 121.4 . . ?
C3 C4 C5 117.2(2) . . ?
C5 C4 H4 121.4 . . ?
C4 C5 N3 129.67(19) . . ?
C6 C5 C4 119.9(2) . . ?
C6 C5 N3 110.33(16) . . ?
C1 C6 C5 122.43(18) . . ?
C1 C6 C7 128.89(17) . . ?
C5 C6 C7 108.46(17) . . ?
C6 C7 C8 100.03(14) . . ?
C17 C7 C6 114.16(15) . . ?
C17 C7 C8 111.39(15) . . ?
C17 C7 C18 108.89(15) . . ?
C18 C7 C6 109.55(15) . . ?
C18 C7 C8 112.68(15) . . ?
C7 C8 H8 107.8 . . ?
C9 C8 C7 119.37(14) . . ?
C9 C8 H8 107.8 . . ?
N3 C8 C7 102.27(15) . . ?
N3 C8 H8 107.8 . . ?
N3 C8 C9 111.11(14) . . ?
C10 C9 C8 118.28(16) . . ?
C14 C9 C8 122.12(15) . . ?
C14 C9 C10 119.59(18) . . ?
C9 C10 C16 122.28(18) . . ?
C11 C10 C9 118.34(17) . . ?
C11 C10 C16 119.32(17) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.48(18) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 119.95(19) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.62(18) . . ?
C14 C13 H13 120.2 . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 121.00(17) . . ?
C13 C14 H14 119.5 . . ?
H15A C15 H15B 108.2 . . ?
C16 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
N3 C15 H15A 109.7 . . ?
N3 C15 H15B 109.7 . . ?
N3 C15 C16 109.69(15) . . ?
C10 C16 C15 115.03(16) . . ?
C10 C16 H16A 108.5 . . ?
C10 C16 H16B 108.5 . . ?
C15 C16 H16A 108.5 . . ?
C15 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
N1 C17 C7 178.4(2) . . ?
N2 C18 C7 178.1(2) . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
C5 N3 C8 107.28(14) . . ?
C5 N3 C15 123.53(15) . . ?
C15 N3 C8 113.42(16) . . ?
C1 O1 C19 118.08(16) . . ?

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 -0.7(4) . . . . ?
C1 C6 C7 C8 165.69(19) . . . . ?
C1 C6 C7 C17 46.7(3) . . . . ?
C1 C6 C7 C18 -75.7(2) . . . . ?
C2 C1 C6 C5 2.9(3) . . . . ?
C2 C1 C6 C7 176.85(18) . . . . ?
C2 C1 O1 C19 5.0(3) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C3 C4 C5 N3 -176.5(2) . . . . ?
C4 C5 C6 C1 -2.5(3) . . . . ?
C4 C5 C6 C7 -177.54(17) . . . . ?
C4 C5 N3 C8 -160.9(2) . . . . ?
C4 C5 N3 C15 -26.0(3) . . . . ?
C5 C6 C7 C8 -19.70(18) . . . . ?
C5 C6 C7 C17 -138.73(17) . . . . ?
C5 C6 C7 C18 98.87(18) . . . . ?
C6 C1 C2 C3 -1.3(3) . . . . ?
C6 C1 O1 C19 -174.97(18) . . . . ?
C6 C5 N3 C8 21.9(2) . . . . ?
C6 C5 N3 C15 156.79(17) . . . . ?
C6 C7 C8 C9 154.17(15) . . . . ?
C6 C7 C8 N3 31.13(16) . . . . ?
C7 C8 C9 C10 -145.50(16) . . . . ?
C7 C8 C9 C14 35.5(2) . . . . ?
C7 C8 N3 C5 -33.36(17) . . . . ?
C7 C8 N3 C15 -173.28(15) . . . . ?
C8 C9 C10 C11 -179.86(16) . . . . ?
C8 C9 C10 C16 2.7(3) . . . . ?
C8 C9 C14 C13 -179.48(17) . . . . ?
C9 C8 N3 C5 -161.82(15) . . . . ?
C9 C8 N3 C15 58.26(19) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C9 C10 C16 C15 -6.6(3) . . . . ?
C10 C9 C14 C13 1.5(3) . . . . ?
C10 C11 C12 C13 0.7(3) . . . . ?
C11 C10 C16 C15 175.96(17) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C12 C13 C14 C9 -1.1(3) . . . . ?
C14 C9 C10 C11 -0.8(3) . . . . ?
C14 C9 C10 C16 -178.27(17) . . . . ?
C16 C10 C11 C12 177.24(18) . . . . ?
C16 C15 N3 C5 165.49(17) . . . . ?
C16 C15 N3 C8 -62.0(2) . . . . ?
C17 C7 C8 C9 -84.79(19) . . . . ?
C17 C7 C8 N3 152.17(14) . . . . ?
C18 C7 C8 C9 37.9(2) . . . . ?
C18 C7 C8 N3 -85.11(17) . . . . ?
N3 C5 C6 C1 174.98(17) . . . . ?
N3 C5 C6 C7 0.0(2) . . . . ?
N3 C8 C9 C10 -26.9(2) . . . . ?
N3 C8 C9 C14 154.09(16) . . . . ?
N3 C15 C16 C10 34.4(2) . . . . ?
O1 C1 C2 C3 178.73(19) . . . . ?
O1 C1 C6 C5 -177.12(16) . . . . ?
O1 C1 C6 C7 -3.2(3) . . . . ?

_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 1.297
_oxdiff_exptl_absorpt_empirical_full_min 0.862
