# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_d-243
_database_code_depnum_ccdc_archive 'CCDC 2168377'
loop_
_audit_author_name
_audit_author_address
ZYCIr
;Guangdong Pharmaceutical University
China
;
_audit_update_record             
;
2022-04-24 deposited with the CCDC.	2022-08-14 downloaded from the CCDC.
;
_audit_creation_date             2022-01-14
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H13 Cl N2 O'
_chemical_formula_sum            'C21 H13 Cl N2 O'
_chemical_formula_weight         344.78
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   12.5768(6)
_cell_length_b                   8.3055(3)
_cell_length_c                   15.5210(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.117(4)
_cell_angle_gamma                90
_cell_volume                     1617.09(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4029
_cell_measurement_temperature    199.99(10)
_cell_measurement_theta_max      29.1200
_cell_measurement_theta_min      2.9220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7003
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.993
_diffrn_reflns_theta_max         24.993
_diffrn_reflns_theta_min         2.631
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_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     -9.00  90.00   1.00    2.13    --   11.90  19.00   0.00   99
  2  ω    -12.00  85.00   1.00    2.13    --   11.90  37.00 -90.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0451087000
_diffrn_orient_matrix_UB_12      0.0162926000
_diffrn_orient_matrix_UB_13      -0.0287299000
_diffrn_orient_matrix_UB_21      0.0340737000
_diffrn_orient_matrix_UB_22      0.0218304000
_diffrn_orient_matrix_UB_23      -0.0325603000
_diffrn_orient_matrix_UB_31      0.0001265000
_diffrn_orient_matrix_UB_32      -0.0810149000
_diffrn_orient_matrix_UB_33      -0.0145239000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2507
_reflns_number_total             2838
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2838
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.042
_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)+(0.0482P)²+0.8890P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1004
_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:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C11(H11), C12(H12), C13(H13),
 C14(H14), C18(H18), C19(H19), C20(H20), C21(H21)
;
_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
Cl1 Cl 0.04261(4) 0.63927(6) 0.43831(3) 0.03166(16) Uani 1 1 d . . . . .
O1 O 0.19522(11) 0.37136(16) 0.32258(8) 0.0307(3) Uani 1 1 d . . . . .
N1 N 0.30040(12) 0.46646(18) 0.53061(9) 0.0253(4) Uani 1 1 d . . . . .
N2 N 0.27642(12) 0.50169(18) 0.44166(9) 0.0237(3) Uani 1 1 d . . . . .
C1 C 0.38949(15) 0.5481(2) 0.57061(11) 0.0255(4) Uani 1 1 d . . . . .
C2 C 0.45106(15) 0.4851(3) 0.64023(12) 0.0316(5) Uani 1 1 d . . . . .
H2 H 0.440028 0.380225 0.658588 0.038 Uiso 1 1 calc R U . . .
C3 C 0.52955(16) 0.5804(3) 0.68238(13) 0.0385(5) Uani 1 1 d . . . . .
H3 H 0.570908 0.538630 0.729209 0.046 Uiso 1 1 calc R U . . .
C4 C 0.54677(16) 0.7356(3) 0.65571(14) 0.0395(5) Uani 1 1 d . . . . .
H4 H 0.598330 0.799117 0.685160 0.047 Uiso 1 1 calc R U . . .
C5 C 0.48698(16) 0.7967(3) 0.58485(14) 0.0364(5) Uani 1 1 d . . . . .
H5 H 0.499421 0.901191 0.566553 0.044 Uiso 1 1 calc R U . . .
C6 C 0.40844(14) 0.7044(2) 0.54042(12) 0.0278(4) Uani 1 1 d . . . . .
C7 C 0.34380(15) 0.7630(2) 0.46568(12) 0.0294(4) Uani 1 1 d . . . . .
H7 H 0.347002 0.871317 0.450988 0.035 Uiso 1 1 calc R U . . .
C8 C 0.28001(14) 0.6650(2) 0.41767(12) 0.0248(4) Uani 1 1 d . . . . .
C9 C 0.20782(15) 0.7180(2) 0.34347(12) 0.0247(4) Uani 1 1 d . . . . .
C10 C 0.09741(14) 0.7095(2) 0.34574(11) 0.0249(4) Uani 1 1 d . . . . .
C11 C 0.02906(16) 0.7597(2) 0.27750(13) 0.0326(5) Uani 1 1 d . . . . .
H11 H -0.044369 0.751580 0.280272 0.039 Uiso 1 1 calc R U . . .
C12 C 0.07152(18) 0.8222(3) 0.20505(13) 0.0390(5) Uani 1 1 d . . . . .
H12 H 0.026421 0.855228 0.158265 0.047 Uiso 1 1 calc R U . . .
C13 C 0.18017(18) 0.8360(3) 0.20161(14) 0.0410(5) Uani 1 1 d . . . . .
H13 H 0.208118 0.880316 0.153057 0.049 Uiso 1 1 calc R U . . .
C14 C 0.24803(16) 0.7842(2) 0.27025(13) 0.0334(5) Uani 1 1 d . . . . .
H14 H 0.321354 0.793701 0.267306 0.040 Uiso 1 1 calc R U . . .
C15 C 0.22465(14) 0.3729(2) 0.39953(12) 0.0239(4) Uani 1 1 d . . . . .
C16 C 0.21418(14) 0.2532(2) 0.46636(11) 0.0242(4) Uani 1 1 d . . . . .
C17 C 0.26147(14) 0.3126(2) 0.54408(11) 0.0239(4) Uani 1 1 d . . . . .
C18 C 0.25640(16) 0.2258(2) 0.62074(12) 0.0309(4) Uani 1 1 d . . . . .
H18 H 0.287299 0.264711 0.672861 0.037 Uiso 1 1 calc R U . . .
C19 C 0.20375(17) 0.0800(2) 0.61610(13) 0.0358(5) Uani 1 1 d . . . . .
H19 H 0.199625 0.019706 0.666235 0.043 Uiso 1 1 calc R U . . .
C20 C 0.15651(18) 0.0203(2) 0.53855(13) 0.0366(5) Uani 1 1 d . . . . .
H20 H 0.121902 -0.078715 0.537821 0.044 Uiso 1 1 calc R U . . .
C21 C 0.16059(16) 0.1062(2) 0.46322(13) 0.0308(4) Uani 1 1 d . . . . .
H21 H 0.128450 0.067358 0.411522 0.037 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C10 1.7384(18) . ?
O1 C15 1.225(2) . ?
N1 N2 1.4224(19) . ?
N1 C1 1.414(2) . ?
N1 C17 1.390(2) . ?
N2 C8 1.408(2) . ?
N2 C15 1.391(2) . ?
C1 C2 1.386(3) . ?
C1 C6 1.406(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.392(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.393(3) . ?
C6 C7 1.452(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.332(3) . ?
C8 C9 1.481(2) . ?
C9 C10 1.393(3) . ?
C9 C14 1.390(3) . ?
C10 C11 1.380(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.380(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.376(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.385(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.450(3) . ?
C16 C17 1.396(2) . ?
C16 C21 1.394(3) . ?
C17 C18 1.397(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.379(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.395(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.374(3) . ?
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
C1 N1 N2 115.69(14) . . ?
C17 N1 N2 106.42(13) . . ?
C17 N1 C1 130.64(15) . . ?
C8 N2 N1 116.50(14) . . ?
C15 N2 N1 110.96(14) . . ?
C15 N2 C8 129.74(15) . . ?
C2 C1 N1 122.82(17) . . ?
C2 C1 C6 120.64(18) . . ?
C6 C1 N1 116.37(16) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.3(2) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.88(19) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.63(19) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.2(2) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C7 118.48(17) . . ?
C5 C6 C1 118.30(18) . . ?
C5 C6 C7 123.20(18) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.51(18) . . ?
C8 C7 H7 119.2 . . ?
N2 C8 C9 117.53(15) . . ?
C7 C8 N2 118.01(17) . . ?
C7 C8 C9 124.36(17) . . ?
C10 C9 C8 121.44(16) . . ?
C14 C9 C8 120.96(17) . . ?
C14 C9 C10 117.55(17) . . ?
C9 C10 Cl1 119.54(14) . . ?
C11 C10 Cl1 118.27(15) . . ?
C11 C10 C9 122.16(17) . . ?
C10 C11 H11 120.6 . . ?
C10 C11 C12 118.87(19) . . ?
C12 C11 H11 120.6 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.41(19) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.20(19) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.77(19) . . ?
C13 C14 H14 119.6 . . ?
O1 C15 N2 124.41(17) . . ?
O1 C15 C16 130.83(17) . . ?
N2 C15 C16 104.75(15) . . ?
C17 C16 C15 108.73(16) . . ?
C21 C16 C15 130.11(17) . . ?
C21 C16 C17 120.97(17) . . ?
N1 C17 C16 109.13(15) . . ?
N1 C17 C18 129.87(17) . . ?
C18 C17 C16 120.74(17) . . ?
C17 C18 H18 121.3 . . ?
C19 C18 C17 117.37(18) . . ?
C19 C18 H18 121.3 . . ?
C18 C19 H19 119.0 . . ?
C18 C19 C20 122.04(19) . . ?
C20 C19 H19 119.0 . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.66(19) . . ?
C21 C20 H20 119.7 . . ?
C16 C21 H21 120.9 . . ?
C20 C21 C16 118.22(18) . . ?
C20 C21 H21 120.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C10 C11 C12 177.25(16) . . . . ?
O1 C15 C16 C17 179.82(19) . . . . ?
O1 C15 C16 C21 -5.2(3) . . . . ?
N1 N2 C8 C7 27.0(2) . . . . ?
N1 N2 C8 C9 -149.67(15) . . . . ?
N1 N2 C15 O1 -179.86(17) . . . . ?
N1 N2 C15 C16 1.20(19) . . . . ?
N1 C1 C2 C3 -172.52(17) . . . . ?
N1 C1 C6 C5 172.19(17) . . . . ?
N1 C1 C6 C7 -6.5(2) . . . . ?
N1 C17 C18 C19 173.78(19) . . . . ?
N2 N1 C1 C2 -151.77(17) . . . . ?
N2 N1 C1 C6 33.1(2) . . . . ?
N2 N1 C17 C16 -0.25(19) . . . . ?
N2 N1 C17 C18 -174.23(19) . . . . ?
N2 C8 C9 C10 62.7(2) . . . . ?
N2 C8 C9 C14 -119.94(19) . . . . ?
N2 C15 C16 C17 -1.33(19) . . . . ?
N2 C15 C16 C21 173.62(18) . . . . ?
C1 N1 N2 C8 -44.2(2) . . . . ?
C1 N1 N2 C15 152.92(15) . . . . ?
C1 N1 C17 C16 -148.32(18) . . . . ?
C1 N1 C17 C18 37.7(3) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C1 C6 C7 C8 -10.8(3) . . . . ?
C2 C1 C6 C5 -3.1(3) . . . . ?
C2 C1 C6 C7 178.19(17) . . . . ?
C2 C3 C4 C5 -1.5(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C1 1.5(3) . . . . ?
C4 C5 C6 C7 -179.89(19) . . . . ?
C5 C6 C7 C8 170.57(19) . . . . ?
C6 C1 C2 C3 2.5(3) . . . . ?
C6 C7 C8 N2 0.3(3) . . . . ?
C6 C7 C8 C9 176.66(17) . . . . ?
C7 C8 C9 C10 -113.8(2) . . . . ?
C7 C8 C9 C14 63.7(3) . . . . ?
C8 N2 C15 O1 20.1(3) . . . . ?
C8 N2 C15 C16 -158.81(17) . . . . ?
C8 C9 C10 Cl1 1.4(2) . . . . ?
C8 C9 C10 C11 179.41(17) . . . . ?
C8 C9 C14 C13 -178.91(18) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C10 C9 C14 C13 -1.4(3) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C11 C12 C13 C14 1.3(3) . . . . ?
C12 C13 C14 C9 -0.2(3) . . . . ?
C14 C9 C10 Cl1 -176.12(14) . . . . ?
C14 C9 C10 C11 1.9(3) . . . . ?
C15 N2 C8 C7 -173.93(18) . . . . ?
C15 N2 C8 C9 9.4(3) . . . . ?
C15 C16 C17 N1 1.0(2) . . . . ?
C15 C16 C17 C18 175.62(17) . . . . ?
C15 C16 C21 C20 -175.13(19) . . . . ?
C16 C17 C18 C19 0.4(3) . . . . ?
C17 N1 N2 C8 162.28(15) . . . . ?
C17 N1 N2 C15 -0.63(19) . . . . ?
C17 N1 C1 C2 -6.0(3) . . . . ?
C17 N1 C1 C6 178.80(17) . . . . ?
C17 C16 C21 C20 -0.7(3) . . . . ?
C17 C18 C19 C20 -0.3(3) . . . . ?
C18 C19 C20 C21 -0.3(3) . . . . ?
C19 C20 C21 C16 0.8(3) . . . . ?
C21 C16 C17 N1 -174.51(16) . . . . ?
C21 C16 C17 C18 0.1(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 1.192
_oxdiff_exptl_absorpt_empirical_full_min 0.813
####################################################################### 
# 
# 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_d-40f
_database_code_depnum_ccdc_archive 'CCDC 2168378'
loop_
_audit_author_name
_audit_author_address
ZYCRh
;Guangdong Pharmaceutical University
China
;
_audit_update_record             
;
2022-04-24 deposited with the CCDC.	2022-08-14 downloaded from the CCDC.
;
_audit_creation_date             2022-01-22
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H14 N2 O3'
_chemical_formula_sum            'C21 H14 N2 O3'
_chemical_formula_weight         342.34
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.3638(11)
_cell_length_b                   7.4704(7)
_cell_length_c                   15.0035(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.451(7)
_cell_angle_gamma                90
_cell_volume                     1605.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2642
_cell_measurement_temperature    179.99(10)
_cell_measurement_theta_max      27.6220
_cell_measurement_theta_min      3.0470
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.14
_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  0.0380
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7251
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.044
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      179.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_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    -63.00 -20.00   1.00    3.00    --  -11.35 -37.00  60.00   43
  2  ω    -19.00  29.00   1.00    3.00    --  -11.35 -99.00  30.00   48
  3  ω    -84.00  16.00   1.00    3.00    --  -11.35 -57.00 150.00  100
  4  ω     36.00  65.00   1.00    3.00    --   11.90-178.00 150.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0478534000
_diffrn_orient_matrix_UB_12      -0.0021971000
_diffrn_orient_matrix_UB_13      -0.0082599000
_diffrn_orient_matrix_UB_21      0.0115420000
_diffrn_orient_matrix_UB_22      0.0439377000
_diffrn_orient_matrix_UB_23      0.0413387000
_diffrn_orient_matrix_UB_31      0.0046805000
_diffrn_orient_matrix_UB_32      -0.0842773000
_diffrn_orient_matrix_UB_33      0.0217609000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2272
_reflns_number_total             2824
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0073(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2824
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.030
_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)+(0.0659P)²+0.2526P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1249
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C5(H5), C18(H18), C21(H21), C2(H2A), C19(H19), C12(H12), C4(H4),
 C9(H9), C3(H3), C20(H20), C11(H11), C10(H10)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
O2 O 0.34902(9) 0.38448(16) 0.52297(8) 0.0317(3) Uani 1 1 d . . . . .
H2 H 0.396552 0.396385 0.496619 0.048 Uiso 1 1 calc R U . . .
O1 O 0.16209(9) 0.4490(2) 0.48173(8) 0.0403(4) Uani 1 1 d . . . . .
O3 O 0.50139(9) 0.6559(2) 0.57825(9) 0.0418(4) Uani 1 1 d . . . . .
N1 N 0.31109(10) 0.6040(2) 0.70413(9) 0.0288(4) Uani 1 1 d . . . . .
N2 N 0.35234(10) 0.6302(2) 0.62256(9) 0.0310(4) Uani 1 1 d . . . . .
C16 C 0.32063(11) 0.6857(3) 0.46255(11) 0.0269(4) Uani 1 1 d . . . . .
C15 C 0.31100(12) 0.5525(2) 0.53832(11) 0.0276(4) Uani 1 1 d . . . . .
C1 C 0.16146(12) 0.5885(2) 0.62240(11) 0.0275(4) Uani 1 1 d . . . . .
C14 C 0.20518(12) 0.5228(3) 0.54384(11) 0.0288(4) Uani 1 1 d . . . . .
C6 C 0.21456(12) 0.6245(2) 0.70301(11) 0.0262(4) Uani 1 1 d . . . . .
C17 C 0.31709(12) 0.6220(3) 0.37553(11) 0.0302(5) Uani 1 1 d . . . . .
H17 H 0.312523 0.499570 0.364693 0.036 Uiso 1 1 calc R U . . .
C13 C 0.44808(13) 0.6500(3) 0.63805(12) 0.0303(4) Uani 1 1 d . . . . .
C7 C 0.38167(13) 0.6277(2) 0.77225(11) 0.0292(4) Uani 1 1 d . . . . .
C8 C 0.46561(13) 0.6550(3) 0.73459(12) 0.0311(5) Uani 1 1 d . . . . .
C5 C 0.16913(13) 0.6724(3) 0.77823(12) 0.0328(5) Uani 1 1 d . . . . .
H5 H 0.203456 0.696219 0.832045 0.039 Uiso 1 1 calc R U . . .
C18 C 0.32034(13) 0.7399(3) 0.30493(12) 0.0349(5) Uani 1 1 d . . . . .
H18 H 0.318693 0.696310 0.246764 0.042 Uiso 1 1 calc R U . . .
C21 C 0.32518(14) 0.8686(3) 0.47711(13) 0.0372(5) Uani 1 1 d . . . . .
H21 H 0.326414 0.912945 0.535103 0.045 Uiso 1 1 calc R U . . .
C2 C 0.06481(12) 0.6038(3) 0.61892(12) 0.0338(5) Uani 1 1 d . . . . .
H2A H 0.029616 0.580888 0.565473 0.041 Uiso 1 1 calc R U . . .
C19 C 0.32599(14) 0.9208(3) 0.31997(13) 0.0397(5) Uani 1 1 d . . . . .
H19 H 0.328519 0.999393 0.272139 0.048 Uiso 1 1 calc R U . . .
C12 C 0.37871(15) 0.6190(3) 0.86521(12) 0.0373(5) Uani 1 1 d . . . . .
H12 H 0.323099 0.598574 0.891423 0.045 Uiso 1 1 calc R U . . .
C4 C 0.07308(14) 0.6842(3) 0.77254(13) 0.0398(5) Uani 1 1 d . . . . .
H4 H 0.042960 0.714472 0.823111 0.048 Uiso 1 1 calc R U . . .
C9 C 0.54916(14) 0.6733(3) 0.78716(13) 0.0394(5) Uani 1 1 d . . . . .
H9 H 0.605453 0.688617 0.761386 0.047 Uiso 1 1 calc R U . . .
C3 C 0.02067(13) 0.6518(3) 0.69267(13) 0.0406(5) Uani 1 1 d . . . . .
H3 H -0.044005 0.662712 0.689352 0.049 Uiso 1 1 calc R U . . .
C20 C 0.32790(15) 0.9860(3) 0.40582(14) 0.0459(5) Uani 1 1 d . . . . .
H20 H 0.331022 1.108696 0.416043 0.055 Uiso 1 1 calc R U . . .
C11 C 0.46166(16) 0.6421(3) 0.91601(13) 0.0444(6) Uani 1 1 d . . . . .
H11 H 0.461295 0.640237 0.977965 0.053 Uiso 1 1 calc R U . . .
C10 C 0.54584(16) 0.6681(3) 0.87853(13) 0.0450(6) Uani 1 1 d . . . . .
H10 H 0.600453 0.682057 0.915401 0.054 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 H2 0.8200 . ?
O2 C15 1.395(2) . ?
O1 C14 1.211(2) . ?
O3 C13 1.225(2) . ?
N1 N2 1.414(2) . ?
N1 C6 1.394(2) . ?
N1 C7 1.394(2) . ?
N2 C15 1.473(2) . ?
N2 C13 1.385(2) . ?
C16 C15 1.526(2) . ?
C16 C17 1.387(2) . ?
C16 C21 1.384(3) . ?
C15 C14 1.545(2) . ?
C1 C14 1.463(2) . ?
C1 C6 1.405(2) . ?
C1 C2 1.390(2) . ?
C6 C5 1.393(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(3) . ?
C13 C8 1.451(2) . ?
C7 C8 1.386(3) . ?
C7 C12 1.400(3) . ?
C8 C9 1.391(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.378(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.372(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.386(3) . ?
C2 H2A 0.9300 . ?
C2 C3 1.365(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.375(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.375(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.386(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.376(3) . ?
C3 H3 0.9300 . ?
C20 H20 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.386(3) . ?
C10 H10 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
C15 O2 H2 109.5 . . ?
C6 N1 N2 117.23(13) . . ?
C6 N1 C7 131.38(15) . . ?
C7 N1 N2 106.69(14) . . ?
N1 N2 C15 121.31(14) . . ?
C13 N2 N1 110.30(14) . . ?
C13 N2 C15 121.00(14) . . ?
C17 C16 C15 118.59(17) . . ?
C21 C16 C15 122.17(16) . . ?
C21 C16 C17 119.04(17) . . ?
O2 C15 N2 111.06(14) . . ?
O2 C15 C16 113.88(14) . . ?
O2 C15 C14 106.22(14) . . ?
N2 C15 C16 109.15(15) . . ?
N2 C15 C14 110.08(14) . . ?
C16 C15 C14 106.27(13) . . ?
C6 C1 C14 121.31(16) . . ?
C2 C1 C14 119.17(15) . . ?
C2 C1 C6 119.37(17) . . ?
O1 C14 C15 118.06(15) . . ?
O1 C14 C1 123.17(16) . . ?
C1 C14 C15 118.75(15) . . ?
N1 C6 C1 117.53(15) . . ?
C5 C6 N1 123.13(16) . . ?
C5 C6 C1 119.30(17) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.12(18) . . ?
C18 C17 H17 119.9 . . ?
O3 C13 N2 123.37(16) . . ?
O3 C13 C8 131.33(17) . . ?
N2 C13 C8 105.27(15) . . ?
N1 C7 C12 130.39(18) . . ?
C8 C7 N1 109.03(15) . . ?
C8 C7 C12 120.50(17) . . ?
C7 C8 C13 108.31(15) . . ?
C7 C8 C9 121.54(17) . . ?
C9 C8 C13 130.07(18) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 C6 119.72(17) . . ?
C4 C5 H5 120.1 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.49(18) . . ?
C19 C18 H18 119.8 . . ?
C16 C21 H21 119.8 . . ?
C16 C21 C20 120.43(18) . . ?
C20 C21 H21 119.8 . . ?
C1 C2 H2A 119.5 . . ?
C3 C2 C1 121.09(17) . . ?
C3 C2 H2A 119.5 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 119.97(19) . . ?
C20 C19 H19 120.0 . . ?
C7 C12 H12 121.5 . . ?
C11 C12 C7 117.0(2) . . ?
C11 C12 H12 121.5 . . ?
C5 C4 H4 119.5 . . ?
C5 C4 C3 121.08(18) . . ?
C3 C4 H4 119.5 . . ?
C8 C9 H9 121.1 . . ?
C10 C9 C8 117.8(2) . . ?
C10 C9 H9 121.1 . . ?
C2 C3 C4 119.43(18) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C21 C20 H20 120.0 . . ?
C19 C20 C21 119.9(2) . . ?
C19 C20 H20 120.0 . . ?
C12 C11 H11 118.7 . . ?
C12 C11 C10 122.58(19) . . ?
C10 C11 H11 118.7 . . ?
C9 C10 C11 120.46(19) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 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
O2 C15 C14 O1 -55.1(2) . . . . ?
O2 C15 C14 C1 126.32(16) . . . . ?
O3 C13 C8 C7 -174.6(2) . . . . ?
O3 C13 C8 C9 2.2(4) . . . . ?
N1 N2 C15 O2 -91.95(18) . . . . ?
N1 N2 C15 C16 141.68(15) . . . . ?
N1 N2 C15 C14 25.4(2) . . . . ?
N1 N2 C13 O3 172.14(18) . . . . ?
N1 N2 C13 C8 -6.1(2) . . . . ?
N1 C6 C5 C4 -177.83(18) . . . . ?
N1 C7 C8 C13 0.5(2) . . . . ?
N1 C7 C8 C9 -176.62(17) . . . . ?
N1 C7 C12 C11 177.57(19) . . . . ?
N2 N1 C6 C1 28.3(2) . . . . ?
N2 N1 C6 C5 -154.01(17) . . . . ?
N2 N1 C7 C8 -4.14(19) . . . . ?
N2 N1 C7 C12 179.17(18) . . . . ?
N2 C15 C14 O1 -175.41(17) . . . . ?
N2 C15 C14 C1 6.0(2) . . . . ?
N2 C13 C8 C7 3.4(2) . . . . ?
N2 C13 C8 C9 -179.80(19) . . . . ?
C16 C15 C14 O1 66.5(2) . . . . ?
C16 C15 C14 C1 -112.07(17) . . . . ?
C16 C17 C18 C19 -0.8(3) . . . . ?
C16 C21 C20 C19 0.1(3) . . . . ?
C15 N2 C13 O3 21.8(3) . . . . ?
C15 N2 C13 C8 -156.38(16) . . . . ?
C15 C16 C17 C18 176.39(15) . . . . ?
C15 C16 C21 C20 -175.85(17) . . . . ?
C1 C6 C5 C4 -0.2(3) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C14 C1 C6 N1 3.1(3) . . . . ?
C14 C1 C6 C5 -174.62(17) . . . . ?
C14 C1 C2 C3 175.12(19) . . . . ?
C6 N1 N2 C15 -44.8(2) . . . . ?
C6 N1 N2 C13 164.99(16) . . . . ?
C6 N1 C7 C8 -158.40(19) . . . . ?
C6 N1 C7 C12 24.9(3) . . . . ?
C6 C1 C14 O1 161.06(18) . . . . ?
C6 C1 C14 C15 -20.4(3) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
C6 C5 C4 C3 -0.9(3) . . . . ?
C17 C16 C15 O2 33.2(2) . . . . ?
C17 C16 C15 N2 157.94(15) . . . . ?
C17 C16 C15 C14 -83.39(19) . . . . ?
C17 C16 C21 C20 -1.2(3) . . . . ?
C17 C18 C19 C20 -0.4(3) . . . . ?
C13 N2 C15 O2 55.1(2) . . . . ?
C13 N2 C15 C16 -71.3(2) . . . . ?
C13 N2 C15 C14 172.46(16) . . . . ?
C13 C8 C9 C10 -178.0(2) . . . . ?
C7 N1 N2 C15 156.69(16) . . . . ?
C7 N1 N2 C13 6.49(19) . . . . ?
C7 N1 C6 C1 -179.57(18) . . . . ?
C7 N1 C6 C5 -1.9(3) . . . . ?
C7 C8 C9 C10 -1.6(3) . . . . ?
C7 C12 C11 C10 -1.7(3) . . . . ?
C8 C7 C12 C11 1.2(3) . . . . ?
C8 C9 C10 C11 1.1(3) . . . . ?
C5 C4 C3 C2 1.4(3) . . . . ?
C18 C19 C20 C21 0.7(3) . . . . ?
C21 C16 C15 O2 -152.11(17) . . . . ?
C21 C16 C15 N2 -27.4(2) . . . . ?
C21 C16 C15 C14 91.31(19) . . . . ?
C21 C16 C17 C18 1.5(3) . . . . ?
C2 C1 C14 O1 -14.5(3) . . . . ?
C2 C1 C14 C15 164.02(17) . . . . ?
C2 C1 C6 N1 178.68(17) . . . . ?
C2 C1 C6 C5 0.9(3) . . . . ?
C12 C7 C8 C13 177.54(17) . . . . ?
C12 C7 C8 C9 0.5(3) . . . . ?
C12 C11 C10 C9 0.6(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 1.596
_oxdiff_exptl_absorpt_empirical_full_min 0.617
