# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_exp_10674
_database_code_depnum_ccdc_archive 'CCDC 2152469'
loop_
_audit_author_name
_audit_author_address
'Zesheng Huang'
; Southern Medical University
China
;
_audit_update_record             
;
2022-02-16 deposited with the CCDC.	2022-04-08 downloaded from the CCDC.
;
_audit_creation_date             2019-09-29
_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         'C14 H11 N3 O'
_chemical_formula_sum            'C14 H11 N3 O'
_chemical_formula_weight         237.26
_chemical_melting_point          ?
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                   13.7128(11)
_cell_length_b                   7.4784(7)
_cell_length_c                   11.7095(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.628(7)
_cell_angle_gamma                90
_cell_volume                     1192.78(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1056
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.8020
_cell_measurement_theta_min      3.8160
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.700
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
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    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4303
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.384
_diffrn_reflns_theta_min         3.245
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1281
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -45.00 -17.00   1.00    1.00    --  -33.50 -57.00  90.00   28
  2  ω    -28.00  52.00   1.00    1.00    --   36.12 -37.00   0.00   80
  3  ω     54.00  81.00   1.00    1.00    --   36.12  57.00-120.00   27
  4  ω     19.00  46.00   1.00    1.00    --   36.12  57.00-120.00   27
  5  ω     60.00 107.00   1.00    1.00    --   36.12  19.00 120.00   47
  6  ω     -4.00  75.00   1.00    1.00    --   36.12 -99.00 -30.00   79
  7  ω      9.00  61.00   1.00    1.00    --   36.12  77.00 150.00   52
  8  ω    123.00 150.00   1.00    1.00    --  108.00 178.00 -90.00   27
  9  ω     60.00  95.00   1.00    1.00    --  108.00 178.00 -90.00   35
 10  ω     93.00 176.00   1.00    1.00    --  108.00  45.00-150.00   83
 11  ω     39.00  67.00   1.00    1.00    --  108.00 -94.00  60.00   28
 12  ω     84.00 109.00   1.00    1.00    --  108.00 -94.00  60.00   25
 13  ω     41.00 129.00   1.00    1.00    --  108.00-141.00 -18.00   88
 14  ω     92.00 131.00   1.00    1.00    --  108.00  61.00-180.00   39
 15  ω     81.00 174.00   1.00    1.00    --  108.00  77.00-120.00   93
 16  ω     40.00 135.00   1.00    1.00    --  108.00 -77.00 120.00   95
;
_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      0.0197994000
_diffrn_orient_matrix_UB_12      0.2025954000
_diffrn_orient_matrix_UB_13      0.0080155000
_diffrn_orient_matrix_UB_21      -0.0987437000
_diffrn_orient_matrix_UB_22      0.0359821000
_diffrn_orient_matrix_UB_23      -0.0732440000
_diffrn_orient_matrix_UB_31      -0.0514803000
_diffrn_orient_matrix_UB_32      0.0089769000
_diffrn_orient_matrix_UB_33      0.1100830000
_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'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1447
_reflns_number_total             2258
_reflns_odcompleteness_completeness 99.83
_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 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0106(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.050
_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)+(0.0408P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1213
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.40615(10) 0.3012(2) 0.41625(11) 0.0682(5) Uani 1 1 d . . . . .
N1 N 0.43704(12) 0.3917(2) 0.23229(13) 0.0515(4) Uani 1 1 d . . . . .
N2 N 0.28559(12) 0.3810(2) 0.26680(13) 0.0543(5) Uani 1 1 d . . . . .
N3 N 0.28487(13) 0.4396(3) 0.15424(14) 0.0641(5) Uani 1 1 d . . . . .
C1 C 0.37932(15) 0.3508(3) 0.31858(16) 0.0518(5) Uani 1 1 d . . . . .
C2 C 0.54143(15) 0.3821(3) 0.23882(17) 0.0502(5) Uani 1 1 d . . . . .
C3 C 0.19566(14) 0.3666(3) 0.31427(17) 0.0538(5) Uani 1 1 d . . . . .
C4 C 0.58346(15) 0.3164(3) 0.14552(17) 0.0568(6) Uani 1 1 d . . . . .
H4 H 0.544039 0.273994 0.081286 0.068 Uiso 1 1 calc R . . . .
C5 C 0.37561(16) 0.4429(3) 0.13778(17) 0.0628(6) Uani 1 1 d . . . . .
H5 H 0.397405 0.476617 0.068604 0.075 Uiso 1 1 calc R . . . .
C6 C 0.18703(16) 0.2575(3) 0.40685(17) 0.0656(6) Uani 1 1 d . . . . .
H6 H 0.240601 0.191673 0.439717 0.079 Uiso 1 1 calc R . . . .
C7 C 0.59895(16) 0.4441(3) 0.33540(18) 0.0613(6) Uani 1 1 d . . . . .
H7 H 0.570387 0.487414 0.398164 0.074 Uiso 1 1 calc R . . . .
C8 C 0.68391(16) 0.3144(3) 0.1484(2) 0.0683(7) Uani 1 1 d . . . . .
H8 H 0.712580 0.270763 0.085831 0.082 Uiso 1 1 calc R . . . .
C9 C 0.69965(17) 0.4403(3) 0.3367(2) 0.0725(7) Uani 1 1 d . . . . .
H9 H 0.739341 0.481242 0.401132 0.087 Uiso 1 1 calc R . . . .
C10 C 0.11540(16) 0.4645(3) 0.2659(2) 0.0682(7) Uani 1 1 d . . . . .
H10 H 0.121259 0.539056 0.203488 0.082 Uiso 1 1 calc R . . . .
C11 C 0.09728(18) 0.2465(4) 0.45099(19) 0.0805(8) Uani 1 1 d . . . . .
H11 H 0.091152 0.173511 0.514075 0.097 Uiso 1 1 calc R . . . .
C12 C 0.74225(17) 0.3767(3) 0.2436(2) 0.0759(7) Uani 1 1 d . . . . .
H12 H 0.810214 0.375972 0.245173 0.091 Uiso 1 1 calc R . . . .
C13 C 0.01778(18) 0.3421(4) 0.4025(2) 0.0821(8) Uani 1 1 d . . . . .
H13 H -0.042155 0.332924 0.431939 0.098 Uiso 1 1 calc R . . . .
C14 C 0.02705(18) 0.4510(4) 0.3104(2) 0.0811(8) Uani 1 1 d . . . . .
H14 H -0.026744 0.516403 0.277732 0.097 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
O1 C1 1.218(2) . ?
N1 C1 1.388(2) . ?
N1 C2 1.427(2) . ?
N1 C5 1.366(2) . ?
N2 N3 1.388(2) . ?
N2 C1 1.375(2) . ?
N2 C3 1.414(2) . ?
N3 C5 1.281(2) . ?
C2 C4 1.383(3) . ?
C2 C7 1.382(3) . ?
C3 C6 1.373(3) . ?
C3 C10 1.387(3) . ?
C4 H4 0.9300 . ?
C4 C8 1.374(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C6 C11 1.391(3) . ?
C7 H7 0.9300 . ?
C7 C9 1.380(3) . ?
C8 H8 0.9300 . ?
C8 C12 1.376(3) . ?
C9 H9 0.9300 . ?
C9 C12 1.379(3) . ?
C10 H10 0.9300 . ?
C10 C14 1.377(3) . ?
C11 H11 0.9300 . ?
C11 C13 1.371(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.368(3) . ?
C14 H14 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
C1 N1 C2 127.09(16) . . ?
C5 N1 C1 107.54(16) . . ?
C5 N1 C2 125.37(17) . . ?
N3 N2 C3 119.10(17) . . ?
C1 N2 N3 111.99(16) . . ?
C1 N2 C3 128.86(17) . . ?
C5 N3 N2 104.38(17) . . ?
O1 C1 N1 127.94(19) . . ?
O1 C1 N2 129.03(19) . . ?
N2 C1 N1 103.03(16) . . ?
C4 C2 N1 118.86(18) . . ?
C7 C2 N1 120.09(18) . . ?
C7 C2 C4 121.0(2) . . ?
C6 C3 N2 121.0(2) . . ?
C6 C3 C10 120.0(2) . . ?
C10 C3 N2 119.1(2) . . ?
C2 C4 H4 120.3 . . ?
C8 C4 C2 119.5(2) . . ?
C8 C4 H4 120.3 . . ?
N1 C5 H5 123.5 . . ?
N3 C5 N1 113.05(18) . . ?
N3 C5 H5 123.5 . . ?
C3 C6 H6 120.4 . . ?
C3 C6 C11 119.3(2) . . ?
C11 C6 H6 120.4 . . ?
C2 C7 H7 120.7 . . ?
C9 C7 C2 118.5(2) . . ?
C9 C7 H7 120.7 . . ?
C4 C8 H8 119.9 . . ?
C4 C8 C12 120.3(2) . . ?
C12 C8 H8 119.9 . . ?
C7 C9 H9 119.6 . . ?
C12 C9 C7 120.9(2) . . ?
C12 C9 H9 119.6 . . ?
C3 C10 H10 120.1 . . ?
C14 C10 C3 119.9(2) . . ?
C14 C10 H10 120.1 . . ?
C6 C11 H11 119.7 . . ?
C13 C11 C6 120.7(2) . . ?
C13 C11 H11 119.7 . . ?
C8 C12 C9 119.8(2) . . ?
C8 C12 H12 120.1 . . ?
C9 C12 H12 120.1 . . ?
C11 C13 H13 120.2 . . ?
C14 C13 C11 119.7(2) . . ?
C14 C13 H13 120.2 . . ?
C10 C14 H14 119.7 . . ?
C13 C14 C10 120.5(2) . . ?
C13 C14 H14 119.7 . . ?

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 C4 C8 176.88(18) . . . . ?
N1 C2 C7 C9 -177.06(19) . . . . ?
N2 N3 C5 N1 -0.5(3) . . . . ?
N2 C3 C6 C11 -179.85(19) . . . . ?
N2 C3 C10 C14 179.5(2) . . . . ?
N3 N2 C1 O1 179.1(2) . . . . ?
N3 N2 C1 N1 -0.6(2) . . . . ?
N3 N2 C3 C6 158.20(19) . . . . ?
N3 N2 C3 C10 -21.7(3) . . . . ?
C1 N1 C2 C4 139.4(2) . . . . ?
C1 N1 C2 C7 -43.0(3) . . . . ?
C1 N1 C5 N3 0.2(3) . . . . ?
C1 N2 N3 C5 0.7(2) . . . . ?
C1 N2 C3 C6 -24.6(3) . . . . ?
C1 N2 C3 C10 155.5(2) . . . . ?
C2 N1 C1 O1 1.0(4) . . . . ?
C2 N1 C1 N2 -179.38(18) . . . . ?
C2 N1 C5 N3 179.83(19) . . . . ?
C2 C4 C8 C12 0.2(3) . . . . ?
C2 C7 C9 C12 0.2(4) . . . . ?
C3 N2 N3 C5 178.35(19) . . . . ?
C3 N2 C1 O1 1.7(4) . . . . ?
C3 N2 C1 N1 -177.95(19) . . . . ?
C3 C6 C11 C13 0.5(4) . . . . ?
C3 C10 C14 C13 0.2(4) . . . . ?
C4 C2 C7 C9 0.4(3) . . . . ?
C4 C8 C12 C9 0.4(4) . . . . ?
C5 N1 C1 O1 -179.4(2) . . . . ?
C5 N1 C1 N2 0.3(2) . . . . ?
C5 N1 C2 C4 -40.2(3) . . . . ?
C5 N1 C2 C7 137.4(2) . . . . ?
C6 C3 C10 C14 -0.4(3) . . . . ?
C6 C11 C13 C14 -0.7(4) . . . . ?
C7 C2 C4 C8 -0.6(3) . . . . ?
C7 C9 C12 C8 -0.6(4) . . . . ?
C10 C3 C6 C11 0.1(3) . . . . ?
C11 C13 C14 C10 0.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.258
_oxdiff_exptl_absorpt_empirical_full_min 0.806
