# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_210501a
_database_code_depnum_ccdc_archive 'CCDC 2165681'
loop_
_audit_author_name
_audit_author_address
'Feng Xu'
;Guizhou University
China
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2023-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 N O2'
_chemical_formula_weight         227.25

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.6581(15)
_cell_length_b                   12.1447(18)
_cell_length_c                   22.107(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2324.6(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    699
_cell_measurement_theta_min      7.2810
_cell_measurement_theta_max      49.4100

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8491
_exptl_absorpt_correction_T_max  0.9523
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 8.1281
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4619
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_sigmaI/netI    0.0688
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.00
_diffrn_reflns_theta_max         66.04
_reflns_number_total             2034
_reflns_number_gt                1063
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0476P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0046(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2034
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1568
_refine_ls_wR_factor_gt          0.1195
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3528(3) 0.15351(18) 0.19369(12) 0.0542(7) Uani 1 1 d . . .
O1 O 0.3865(3) 0.34147(16) 0.20119(11) 0.0805(8) Uani 1 1 d . . .
O2 O 0.2011(2) 0.13295(18) 0.31182(10) 0.0691(7) Uani 1 1 d . . .
C1 C 0.3864(4) 0.2494(2) 0.22407(15) 0.0586(9) Uani 1 1 d . . .
C2 C 0.4255(4) 0.2216(2) 0.28799(14) 0.0576(8) Uani 1 1 d . . .
H2 H 0.5375 0.2218 0.2944 0.069 Uiso 1 1 calc R . .
C3 C 0.3417(4) 0.2854(3) 0.33844(15) 0.0710(10) Uani 1 1 d . . .
H3A H 0.2784 0.3443 0.3222 0.085 Uiso 1 1 calc R . .
H3B H 0.4137 0.3155 0.3677 0.085 Uiso 1 1 calc R . .
C4 C 0.2422(4) 0.1930(3) 0.36614(16) 0.0738(11) Uani 1 1 d . . .
H4 H 0.1550 0.2178 0.3909 0.089 Uiso 1 1 calc R . .
C5 C 0.3489(4) 0.1109(3) 0.39605(17) 0.0763(11) Uani 1 1 d . . .
H5 H 0.3633 0.1014 0.4374 0.092 Uiso 1 1 calc R . .
C6 C 0.4175(4) 0.0553(3) 0.35253(15) 0.0704(10) Uani 1 1 d . . .
H6 H 0.4875 -0.0023 0.3566 0.085 Uiso 1 1 calc R . .
C7 C 0.3582(3) 0.1052(2) 0.29521(14) 0.0549(8) Uani 1 1 d . . .
C8 C 0.3638(4) 0.0556(2) 0.23315(13) 0.0580(9) Uani 1 1 d . . .
H8A H 0.4598 0.0163 0.2265 0.070 Uiso 1 1 calc R . .
H8B H 0.2778 0.0058 0.2266 0.070 Uiso 1 1 calc R . .
C9 C 0.3253(4) 0.1436(2) 0.13134(15) 0.0590(9) Uani 1 1 d . . .
C10 C 0.3538(5) 0.0444(3) 0.10334(17) 0.0965(14) Uani 1 1 d . . .
H10 H 0.3942 -0.0141 0.1254 0.116 Uiso 1 1 calc R . .
C11 C 0.3223(7) 0.0316(4) 0.04240(19) 0.130(2) Uani 1 1 d . . .
H11 H 0.3422 -0.0358 0.0241 0.156 Uiso 1 1 calc R . .
C12 C 0.2631(7) 0.1149(4) 0.00848(19) 0.122(2) Uani 1 1 d . . .
H12 H 0.2412 0.1051 -0.0324 0.146 Uiso 1 1 calc R . .
C13 C 0.2369(6) 0.2130(4) 0.03620(17) 0.1137(18) Uani 1 1 d . . .
H13 H 0.1974 0.2712 0.0137 0.136 Uiso 1 1 calc R . .
C14 C 0.2674(5) 0.2286(3) 0.09681(16) 0.0872(13) Uani 1 1 d . . .
H14 H 0.2487 0.2968 0.1145 0.105 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.376(4) . ?
N1 C9 1.404(4) . ?
N1 C8 1.478(3) . ?
O1 C1 1.227(3) . ?
O2 C7 1.449(3) . ?
O2 C4 1.450(4) . ?
C1 C2 1.492(4) . ?
C2 C7 1.538(4) . ?
C2 C3 1.540(4) . ?
C2 H2 0.9800 . ?
C3 C4 1.541(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.512(5) . ?
C4 H4 0.9800 . ?
C5 C6 1.317(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.495(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.499(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.376(4) . ?
C9 C14 1.379(4) . ?
C10 C11 1.383(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.359(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.358(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.379(5) . ?
C13 H13 0.9300 . ?
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 C9 126.0(3) . . ?
C1 N1 C8 112.3(3) . . ?
C9 N1 C8 121.4(2) . . ?
C7 O2 C4 95.5(2) . . ?
O1 C1 N1 124.8(3) . . ?
O1 C1 C2 126.6(3) . . ?
N1 C1 C2 108.6(3) . . ?
C1 C2 C7 102.7(2) . . ?
C1 C2 C3 117.7(3) . . ?
C7 C2 C3 102.1(3) . . ?
C1 C2 H2 111.2 . . ?
C7 C2 H2 111.2 . . ?
C3 C2 H2 111.2 . . ?
C2 C3 C4 100.7(2) . . ?
C2 C3 H3A 111.6 . . ?
C4 C3 H3A 111.6 . . ?
C2 C3 H3B 111.6 . . ?
C4 C3 H3B 111.6 . . ?
H3A C3 H3B 109.4 . . ?
O2 C4 C5 100.4(3) . . ?
O2 C4 C3 100.1(3) . . ?
C5 C4 C3 108.2(3) . . ?
O2 C4 H4 115.4 . . ?
C5 C4 H4 115.4 . . ?
C3 C4 H4 115.4 . . ?
C6 C5 C4 107.1(3) . . ?
C6 C5 H5 126.4 . . ?
C4 C5 H5 126.4 . . ?
C5 C6 C7 104.9(3) . . ?
C5 C6 H6 127.6 . . ?
C7 C6 H6 127.6 . . ?
O2 C7 C6 101.6(3) . . ?
O2 C7 C8 110.8(3) . . ?
C6 C7 C8 127.0(3) . . ?
O2 C7 C2 99.7(2) . . ?
C6 C7 C2 109.3(3) . . ?
C8 C7 C2 105.2(3) . . ?
N1 C8 C7 102.4(2) . . ?
N1 C8 H8A 111.3 . . ?
C7 C8 H8A 111.3 . . ?
N1 C8 H8B 111.3 . . ?
C7 C8 H8B 111.3 . . ?
H8A C8 H8B 109.2 . . ?
C10 C9 C14 118.1(3) . . ?
C10 C9 N1 119.1(3) . . ?
C14 C9 N1 122.7(3) . . ?
C9 C10 C11 120.1(4) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 121.9(4) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C13 C12 C11 117.8(4) . . ?
C13 C12 H12 121.1 . . ?
C11 C12 H12 121.1 . . ?
C12 C13 C14 121.8(4) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C13 C14 C9 120.3(4) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?

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
C9 N1 C1 O1 5.3(5) . . . . ?
C8 N1 C1 O1 179.4(3) . . . . ?
C9 N1 C1 C2 -173.3(3) . . . . ?
C8 N1 C1 C2 0.7(3) . . . . ?
O1 C1 C2 C7 163.2(3) . . . . ?
N1 C1 C2 C7 -18.2(3) . . . . ?
O1 C1 C2 C3 52.1(5) . . . . ?
N1 C1 C2 C3 -129.3(3) . . . . ?
C1 C2 C3 C4 112.2(3) . . . . ?
C7 C2 C3 C4 0.6(3) . . . . ?
C7 O2 C4 C5 -49.7(3) . . . . ?
C7 O2 C4 C3 61.2(3) . . . . ?
C2 C3 C4 O2 -37.3(3) . . . . ?
C2 C3 C4 C5 67.2(3) . . . . ?
O2 C4 C5 C6 31.1(4) . . . . ?
C3 C4 C5 C6 -73.3(4) . . . . ?
C4 C5 C6 C7 1.9(4) . . . . ?
C4 O2 C7 C6 51.9(3) . . . . ?
C4 O2 C7 C8 -170.7(3) . . . . ?
C4 O2 C7 C2 -60.3(3) . . . . ?
C5 C6 C7 O2 -34.5(3) . . . . ?
C5 C6 C7 C8 -162.1(3) . . . . ?
C5 C6 C7 C2 70.2(4) . . . . ?
C1 C2 C7 O2 -86.3(3) . . . . ?
C3 C2 C7 O2 36.1(3) . . . . ?
C1 C2 C7 C6 167.7(3) . . . . ?
C3 C2 C7 C6 -69.9(3) . . . . ?
C1 C2 C7 C8 28.6(3) . . . . ?
C3 C2 C7 C8 151.0(3) . . . . ?
C1 N1 C8 C7 17.5(3) . . . . ?
C9 N1 C8 C7 -168.1(3) . . . . ?
O2 C7 C8 N1 79.0(3) . . . . ?
C6 C7 C8 N1 -157.2(3) . . . . ?
C2 C7 C8 N1 -27.9(3) . . . . ?
C1 N1 C9 C10 154.3(3) . . . . ?
C8 N1 C9 C10 -19.3(5) . . . . ?
C1 N1 C9 C14 -27.3(5) . . . . ?
C8 N1 C9 C14 159.2(3) . . . . ?
C14 C9 C10 C11 -0.9(7) . . . . ?
N1 C9 C10 C11 177.7(4) . . . . ?
C9 C10 C11 C12 0.0(9) . . . . ?
C10 C11 C12 C13 0.8(9) . . . . ?
C11 C12 C13 C14 -0.6(9) . . . . ?
C12 C13 C14 C9 -0.3(8) . . . . ?
C10 C9 C14 C13 1.0(6) . . . . ?
N1 C9 C14 C13 -177.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        66.04
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_220531d
_database_code_depnum_ccdc_archive 'CCDC 2179840'
loop_
_audit_author_name
_audit_author_address
'Feng Xu'
;Guizhou University
China
;
_audit_update_record             
;
2022-06-17 deposited with the CCDC.	2023-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 Cl N O2'
_chemical_formula_weight         261.70

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.6538(11)
_cell_length_b                   9.0781(8)
_cell_length_c                   10.6852(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.522(4)
_cell_angle_gamma                90.00
_cell_volume                     1255.83(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1508
_cell_measurement_theta_min      2.741
_cell_measurement_theta_max      24.051

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8881
_exptl_absorpt_correction_T_max  0.9653
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5847
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_av_sigmaI/netI    0.0542
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.74
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2215
_reflns_number_gt                1379
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0365P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2215
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1024
_refine_ls_wR_factor_gt          0.0946
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.33858(5) 0.16146(8) 0.40584(8) 0.0851(3) Uani 1 1 d . . .
N1 N 0.89193(13) 0.16353(18) 0.37126(17) 0.0421(5) Uani 1 1 d . . .
O1 O 0.88265(13) 0.36019(19) 0.50765(18) 0.0715(5) Uani 1 1 d . . .
O2 O 0.68740(10) 0.23959(17) 0.17670(14) 0.0511(4) Uani 1 1 d . . .
C1 C 0.84181(17) 0.2565(3) 0.4349(2) 0.0480(6) Uani 1 1 d . . .
C2 C 0.73043(17) 0.2078(2) 0.4007(2) 0.0466(6) Uani 1 1 d . . .
H2 H 0.7197 0.1459 0.4703 0.056 Uiso 1 1 calc R . .
C3 C 0.64603(18) 0.3287(3) 0.3556(2) 0.0567(7) Uani 1 1 d . . .
H3A H 0.5968 0.3232 0.4038 0.068 Uiso 1 1 calc R . .
H3B H 0.6759 0.4267 0.3648 0.068 Uiso 1 1 calc R . .
C4 C 0.59632(17) 0.2858(3) 0.2090(2) 0.0551(7) Uani 1 1 d . . .
H4 H 0.5554 0.3634 0.1524 0.066 Uiso 1 1 calc R . .
C5 C 0.5409(2) 0.1389(3) 0.2027(3) 0.0682(8) Uani 1 1 d . . .
H5 H 0.4699 0.1240 0.1780 0.082 Uiso 1 1 calc R . .
C6 C 0.61381(19) 0.0365(3) 0.2393(3) 0.0660(8) Uani 1 1 d . . .
H6 H 0.6047 -0.0647 0.2439 0.079 Uiso 1 1 calc R . .
C7 C 0.71499(17) 0.1193(2) 0.2720(2) 0.0446(6) Uani 1 1 d . . .
C8 C 0.81999(16) 0.0574(2) 0.2818(2) 0.0474(6) Uani 1 1 d . . .
H8A H 0.8288 -0.0410 0.3191 0.057 Uiso 1 1 calc R . .
H8B H 0.8301 0.0544 0.1960 0.057 Uiso 1 1 calc R . .
C9 C 0.99894(16) 0.1641(2) 0.3837(2) 0.0401(5) Uani 1 1 d . . .
C10 C 1.06708(18) 0.2730(3) 0.4547(2) 0.0554(7) Uani 1 1 d . . .
H10 H 1.0430 0.3466 0.4980 0.067 Uiso 1 1 calc R . .
C11 C 1.17036(18) 0.2715(3) 0.4609(3) 0.0600(7) Uani 1 1 d . . .
H11 H 1.2146 0.3450 0.5071 0.072 Uiso 1 1 calc R . .
C12 C 1.20807(18) 0.1613(3) 0.3987(2) 0.0535(6) Uani 1 1 d . . .
C13 C 1.14221(18) 0.0519(3) 0.3299(2) 0.0602(7) Uani 1 1 d . . .
H13 H 1.1672 -0.0224 0.2883 0.072 Uiso 1 1 calc R . .
C14 C 1.03870(18) 0.0529(3) 0.3230(2) 0.0552(7) Uani 1 1 d . . .
H14 H 0.9952 -0.0215 0.2772 0.066 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
Cl1 C12 1.759(2) . ?
N1 C1 1.393(3) . ?
N1 C9 1.424(2) . ?
N1 C8 1.487(3) . ?
O1 C1 1.235(3) . ?
O2 C4 1.454(2) . ?
O2 C7 1.458(2) . ?
C1 C2 1.513(3) . ?
C2 C7 1.548(3) . ?
C2 C3 1.554(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.546(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.524(3) . ?
C4 H4 0.9800 . ?
C5 C6 1.327(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.513(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.512(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C14 1.399(3) . ?
C9 C10 1.404(3) . ?
C10 C11 1.391(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(3) . ?
C13 C14 1.392(3) . ?
C13 H13 0.9300 . ?
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 C9 126.93(18) . . ?
C1 N1 C8 112.35(17) . . ?
C9 N1 C8 120.72(16) . . ?
C4 O2 C7 95.81(15) . . ?
O1 C1 N1 125.1(2) . . ?
O1 C1 C2 126.39(19) . . ?
N1 C1 C2 108.47(19) . . ?
C1 C2 C7 102.08(16) . . ?
C1 C2 C3 117.26(19) . . ?
C7 C2 C3 102.28(18) . . ?
C1 C2 H2 111.5 . . ?
C7 C2 H2 111.5 . . ?
C3 C2 H2 111.5 . . ?
C4 C3 C2 100.36(18) . . ?
C4 C3 H3A 111.7 . . ?
C2 C3 H3A 111.7 . . ?
C4 C3 H3B 111.7 . . ?
C2 C3 H3B 111.7 . . ?
H3A C3 H3B 109.5 . . ?
O2 C4 C5 100.77(19) . . ?
O2 C4 C3 100.35(17) . . ?
C5 C4 C3 108.5(2) . . ?
O2 C4 H4 115.1 . . ?
C5 C4 H4 115.1 . . ?
C3 C4 H4 115.1 . . ?
C6 C5 C4 106.6(2) . . ?
C6 C5 H5 126.7 . . ?
C4 C5 H5 126.7 . . ?
C5 C6 C7 105.3(2) . . ?
C5 C6 H6 127.3 . . ?
C7 C6 H6 127.3 . . ?
O2 C7 C8 110.84(16) . . ?
O2 C7 C6 101.34(18) . . ?
C8 C7 C6 127.37(19) . . ?
O2 C7 C2 99.42(16) . . ?
C8 C7 C2 105.83(18) . . ?
C6 C7 C2 108.64(17) . . ?
N1 C8 C7 102.80(17) . . ?
N1 C8 H8A 111.2 . . ?
C7 C8 H8A 111.2 . . ?
N1 C8 H8B 111.2 . . ?
C7 C8 H8B 111.2 . . ?
H8A C8 H8B 109.1 . . ?
C14 C9 C10 118.1(2) . . ?
C14 C9 N1 119.44(19) . . ?
C10 C9 N1 122.49(19) . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 120.7(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 119.6(2) . . ?
C11 C12 Cl1 120.26(19) . . ?
C13 C12 Cl1 120.10(19) . . ?
C12 C13 C14 120.0(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 121.2(2) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?

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
C9 N1 C1 O1 4.1(4) . . . . ?
C8 N1 C1 O1 -175.1(2) . . . . ?
C9 N1 C1 C2 -175.39(18) . . . . ?
C8 N1 C1 C2 5.3(2) . . . . ?
O1 C1 C2 C7 159.4(2) . . . . ?
N1 C1 C2 C7 -21.1(2) . . . . ?
O1 C1 C2 C3 48.6(3) . . . . ?
N1 C1 C2 C3 -131.9(2) . . . . ?
C1 C2 C3 C4 111.5(2) . . . . ?
C7 C2 C3 C4 0.8(2) . . . . ?
C7 O2 C4 C5 -50.0(2) . . . . ?
C7 O2 C4 C3 61.34(19) . . . . ?
C2 C3 C4 O2 -37.4(2) . . . . ?
C2 C3 C4 C5 67.8(2) . . . . ?
O2 C4 C5 C6 31.4(3) . . . . ?
C3 C4 C5 C6 -73.4(2) . . . . ?
C4 C5 C6 C7 1.4(3) . . . . ?
C4 O2 C7 C8 -170.99(18) . . . . ?
C4 O2 C7 C6 51.39(19) . . . . ?
C4 O2 C7 C2 -59.94(17) . . . . ?
C5 C6 C7 O2 -33.8(2) . . . . ?
C5 C6 C7 C8 -161.4(2) . . . . ?
C5 C6 C7 C2 70.3(3) . . . . ?
C1 C2 C7 O2 -86.00(18) . . . . ?
C3 C2 C7 O2 35.74(19) . . . . ?
C1 C2 C7 C8 29.0(2) . . . . ?
C3 C2 C7 C8 150.69(17) . . . . ?
C1 C2 C7 C6 168.56(19) . . . . ?
C3 C2 C7 C6 -69.7(2) . . . . ?
C1 N1 C8 C7 13.3(2) . . . . ?
C9 N1 C8 C7 -166.06(18) . . . . ?
O2 C7 C8 N1 80.9(2) . . . . ?
C6 C7 C8 N1 -155.3(2) . . . . ?
C2 C7 C8 N1 -25.9(2) . . . . ?
C1 N1 C9 C14 173.4(2) . . . . ?
C8 N1 C9 C14 -7.4(3) . . . . ?
C1 N1 C9 C10 -6.8(3) . . . . ?
C8 N1 C9 C10 172.37(19) . . . . ?
C14 C9 C10 C11 1.7(3) . . . . ?
N1 C9 C10 C11 -178.1(2) . . . . ?
C9 C10 C11 C12 -1.0(4) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C10 C11 C12 Cl1 179.40(18) . . . . ?
C11 C12 C13 C14 0.2(4) . . . . ?
Cl1 C12 C13 C14 -179.19(19) . . . . ?
C12 C13 C14 C9 0.6(4) . . . . ?
C10 C9 C14 C13 -1.5(3) . . . . ?
N1 C9 C14 C13 178.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_210309a_tw
_database_code_depnum_ccdc_archive 'CCDC 2165682'
loop_
_audit_author_name
_audit_author_address
'Feng Xu'
;Guizhou University
China
;
_audit_update_record             
;
2022-04-11 deposited with the CCDC.	2023-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 N O'
_chemical_formula_weight         209.24

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

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                   5.9303(7)
_cell_length_b                   7.6388(9)
_cell_length_c                   23.149(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.506(3)
_cell_angle_gamma                90
_cell_volume                     1045.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    901
_cell_measurement_theta_min      7.6460
_cell_measurement_theta_max      69.3890

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.667
_shelx_estimated_absorpt_T_min   0.776
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7763
_exptl_absorpt_correction_T_max  0.9803
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 8.1281
_diffrn_reflns_number            1776
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         6.102
_diffrn_reflns_theta_max         66.032
_diffrn_reflns_theta_full        66.032
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             1776
_reflns_number_gt                1358
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _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. Completness statistics refer to single and 
 composite reflections containing twin component 1 only. 
;

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1776
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0905
_refine_ls_wR_factor_ref         0.2474
_refine_ls_wR_factor_gt          0.2340
_refine_ls_goodness_of_fit_ref   1.395
_refine_ls_restrained_S_all      1.395
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.8348(5) 0.5169(4) 0.25268(11) 0.0568(9) Uani 1 1 d . . . . .
N1 N 0.4833(5) 0.3859(4) 0.25778(12) 0.0379(8) Uani 1 1 d . . . . .
C1 C 0.6636(6) 0.4468(5) 0.22974(16) 0.0408(9) Uani 1 1 d . . . . .
C2 C 0.6132(7) 0.4104(5) 0.16788(15) 0.0404(9) Uani 1 1 d . . . . .
C3 C 0.7423(7) 0.4494(5) 0.12253(17) 0.0495(10) Uani 1 1 d . . . . .
H3 H 0.879627 0.507762 0.128898 0.059 Uiso 1 1 calc R U . . .
C4 C 0.6619(8) 0.3993(5) 0.06746(18) 0.0569(12) Uani 1 1 d . . . . .
H4 H 0.743894 0.425475 0.035935 0.068 Uiso 1 1 calc R U . . .
C5 C 0.4562(9) 0.3089(6) 0.05913(18) 0.0620(13) Uani 1 1 d . . . . .
H5 H 0.404632 0.273368 0.021984 0.074 Uiso 1 1 calc R U . . .
C6 C 0.3280(8) 0.2713(5) 0.10519(18) 0.0552(11) Uani 1 1 d . . . . .
H6 H 0.191177 0.211920 0.099340 0.066 Uiso 1 1 calc R U . . .
C7 C 0.4086(7) 0.3242(5) 0.15972(16) 0.0415(9) Uani 1 1 d . . . . .
C8 C 0.3141(6) 0.3027(5) 0.21726(15) 0.0427(9) Uani 1 1 d . . . . .
H8A H 0.168695 0.360572 0.217842 0.051 Uiso 1 1 calc R U . . .
H8B H 0.296344 0.179893 0.226546 0.051 Uiso 1 1 calc R U . . .
C9 C 0.4708(6) 0.3747(4) 0.31843(16) 0.0394(9) Uani 1 1 d . . . . .
C10 C 0.6439(7) 0.4331(5) 0.35777(17) 0.0487(10) Uani 1 1 d . . . . .
H10 H 0.772273 0.484853 0.344637 0.058 Uiso 1 1 calc R U . . .
C11 C 0.6238(8) 0.4138(5) 0.41653(17) 0.0532(11) Uani 1 1 d . . . . .
H11 H 0.738948 0.454248 0.442743 0.064 Uiso 1 1 calc R U . . .
C12 C 0.4353(8) 0.3354(5) 0.43706(18) 0.0555(12) Uani 1 1 d . . . . .
H12 H 0.425514 0.320407 0.476653 0.067 Uiso 1 1 calc R U . . .
C13 C 0.2642(8) 0.2806(6) 0.39850(18) 0.0579(12) Uani 1 1 d . . . . .
H13 H 0.135625 0.230096 0.411962 0.069 Uiso 1 1 calc R U . . .
C14 C 0.2803(7) 0.2993(5) 0.33975(17) 0.0486(10) Uani 1 1 d . . . . .
H14 H 0.162345 0.260967 0.313988 0.058 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
O1 C1 1.231(4) . ?
N1 C1 1.375(5) . ?
N1 C9 1.414(4) . ?
N1 C8 1.464(5) . ?
C1 C2 1.466(5) . ?
C2 C3 1.380(5) . ?
C2 C7 1.380(6) . ?
C3 C4 1.380(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.402(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.375(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.494(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.391(5) . ?
C9 C14 1.393(5) . ?
C10 C11 1.383(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.385(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.364(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.378(6) . ?
C13 H13 0.9300 . ?
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 C9 126.3(3) . . ?
C1 N1 C8 111.3(3) . . ?
C9 N1 C8 121.6(3) . . ?
O1 C1 N1 126.1(3) . . ?
O1 C1 C2 127.0(3) . . ?
N1 C1 C2 106.9(3) . . ?
C3 C2 C7 122.2(4) . . ?
C3 C2 C1 128.3(4) . . ?
C7 C2 C1 109.5(3) . . ?
C2 C3 C4 118.1(4) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
C3 C4 C5 119.8(4) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 121.3(4) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C7 C6 C5 118.2(4) . . ?
C7 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C6 C7 C2 120.3(4) . . ?
C6 C7 C8 131.2(4) . . ?
C2 C7 C8 108.5(3) . . ?
N1 C8 C7 103.7(3) . . ?
N1 C8 H8A 111.0 . . ?
C7 C8 H8A 111.0 . . ?
N1 C8 H8B 111.0 . . ?
C7 C8 H8B 111.0 . . ?
H8A C8 H8B 109.0 . . ?
C10 C9 C14 118.6(4) . . ?
C10 C9 N1 122.5(3) . . ?
C14 C9 N1 118.9(4) . . ?
C11 C10 C9 119.6(4) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 121.2(4) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 119.2(4) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 120.6(4) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C9 120.9(4) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?

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
C9 N1 C1 O1 -7.4(6) . . . . ?
C8 N1 C1 O1 -177.3(4) . . . . ?
C9 N1 C1 C2 172.0(3) . . . . ?
C8 N1 C1 C2 2.1(4) . . . . ?
O1 C1 C2 C3 -1.5(7) . . . . ?
N1 C1 C2 C3 179.1(4) . . . . ?
O1 C1 C2 C7 177.6(4) . . . . ?
N1 C1 C2 C7 -1.8(4) . . . . ?
C7 C2 C3 C4 -0.1(6) . . . . ?
C1 C2 C3 C4 178.9(4) . . . . ?
C2 C3 C4 C5 -1.1(6) . . . . ?
C3 C4 C5 C6 1.4(7) . . . . ?
C4 C5 C6 C7 -0.4(7) . . . . ?
C5 C6 C7 C2 -0.8(6) . . . . ?
C5 C6 C7 C8 -179.3(4) . . . . ?
C3 C2 C7 C6 1.1(6) . . . . ?
C1 C2 C7 C6 -178.1(3) . . . . ?
C3 C2 C7 C8 179.9(3) . . . . ?
C1 C2 C7 C8 0.8(4) . . . . ?
C1 N1 C8 C7 -1.7(4) . . . . ?
C9 N1 C8 C7 -172.1(3) . . . . ?
C6 C7 C8 N1 179.2(4) . . . . ?
C2 C7 C8 N1 0.5(4) . . . . ?
C1 N1 C9 C10 2.7(5) . . . . ?
C8 N1 C9 C10 171.6(3) . . . . ?
C1 N1 C9 C14 -176.0(3) . . . . ?
C8 N1 C9 C14 -7.0(5) . . . . ?
C14 C9 C10 C11 0.5(6) . . . . ?
N1 C9 C10 C11 -178.1(3) . . . . ?
C9 C10 C11 C12 0.7(6) . . . . ?
C10 C11 C12 C13 -1.7(7) . . . . ?
C11 C12 C13 C14 1.4(7) . . . . ?
C12 C13 C14 C9 -0.1(6) . . . . ?
C10 C9 C14 C13 -0.8(6) . . . . ?
N1 C9 C14 C13 177.9(3) . . . . ?

_refine_diff_density_max         0.282
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_220823b
_database_code_depnum_ccdc_archive 'CCDC 2209873'
loop_
_audit_author_name
_audit_author_address
'Feng Xu'
;Guizhou University
China
;
_audit_update_record             
;
2022-09-27 deposited with the CCDC.	2023-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 Br N O2'
_chemical_formula_weight         306.16

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.4795(4)
_cell_length_b                   11.4206(9)
_cell_length_c                   19.3592(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1211.48(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2386
_cell_measurement_theta_min      2.759
_cell_measurement_theta_max      26.058

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    3.385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3445
_exptl_absorpt_correction_T_max  0.4299
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5833
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_sigmaI/netI    0.0589
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2136
_reflns_number_gt                1786
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0483P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.460(15)
_refine_ls_number_reflns         2136
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0881
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.77231(9) 0.88943(5) 0.01902(2) 0.0541(2) Uani 1 1 d . . .
N1 N 0.6262(6) 0.7983(3) 0.29395(15) 0.0239(8) Uani 1 1 d . . .
O1 O 0.7562(5) 0.90620(19) 0.15998(12) 0.0273(6) Uani 1 1 d . . .
O2 O 0.5195(8) 0.6301(3) 0.23790(17) 0.0555(10) Uani 1 1 d . . .
C1 C 0.6554(8) 0.7130(4) 0.2463(2) 0.0317(11) Uani 1 1 d . . .
C2 C 0.8831(9) 0.7348(4) 0.2064(2) 0.0347(11) Uani 1 1 d . . .
H2 H 1.0224 0.6921 0.2257 0.042 Uiso 1 1 calc R . .
C3 C 0.8699(10) 0.7225(4) 0.1281(2) 0.0403(12) Uani 1 1 d . . .
H3A H 1.0026 0.6753 0.1101 0.048 Uiso 1 1 calc R . .
H3B H 0.7151 0.6900 0.1132 0.048 Uiso 1 1 calc R . .
C4 C 0.8956(8) 0.8505(4) 0.1082(2) 0.0331(11) Uani 1 1 d . . .
C5 C 1.1464(8) 0.8927(4) 0.1232(2) 0.0415(11) Uani 1 1 d . . .
H5 H 1.2706 0.9078 0.0917 0.050 Uiso 1 1 calc R . .
C6 C 1.1548(8) 0.9040(4) 0.1901(2) 0.0403(11) Uani 1 1 d . . .
H6 H 1.2864 0.9296 0.2164 0.048 Uiso 1 1 calc R . .
C7 C 0.9100(8) 0.8673(3) 0.2158(2) 0.0267(9) Uani 1 1 d . . .
C8 C 0.7992(8) 0.8949(3) 0.28383(19) 0.0282(9) Uani 1 1 d . . .
H8A H 0.9217 0.8962 0.3200 0.034 Uiso 1 1 calc R . .
H8B H 0.7159 0.9698 0.2828 0.034 Uiso 1 1 calc R . .
C9 C 0.4480(8) 0.8023(3) 0.34692(19) 0.0244(9) Uani 1 1 d . . .
C10 C 0.4239(9) 0.9030(4) 0.3854(2) 0.0345(11) Uani 1 1 d . . .
H10 H 0.5257 0.9666 0.3771 0.041 Uiso 1 1 calc R . .
C11 C 0.2494(10) 0.9089(4) 0.4357(2) 0.0437(11) Uani 1 1 d . . .
H11 H 0.2343 0.9772 0.4615 0.052 Uiso 1 1 calc R . .
C12 C 0.0972(10) 0.8175(4) 0.4492(2) 0.0421(12) Uani 1 1 d . . .
H12 H -0.0225 0.8233 0.4831 0.051 Uiso 1 1 calc R . .
C13 C 0.1249(10) 0.7171(4) 0.4116(2) 0.0443(12) Uani 1 1 d . . .
H13 H 0.0241 0.6534 0.4206 0.053 Uiso 1 1 calc R . .
C14 C 0.2986(9) 0.7086(4) 0.3609(2) 0.0364(11) Uani 1 1 d . . .
H14 H 0.3154 0.6394 0.3360 0.044 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
Br1 C4 1.906(4) . ?
N1 C1 1.350(5) . ?
N1 C9 1.417(5) . ?
N1 C8 1.468(5) . ?
O1 C4 1.412(5) . ?
O1 C7 1.440(5) . ?
O2 C1 1.216(5) . ?
C1 C2 1.489(6) . ?
C2 C3 1.524(6) . ?
C2 C7 1.531(5) . ?
C2 H2 0.9800 . ?
C3 C4 1.518(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.486(6) . ?
C5 C6 1.302(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.491(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.484(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C14 1.374(6) . ?
C9 C10 1.376(5) . ?
C10 C11 1.368(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.360(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.367(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(6) . ?
C13 H13 0.9300 . ?
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 C9 126.8(3) . . ?
C1 N1 C8 112.0(3) . . ?
C9 N1 C8 121.2(3) . . ?
C4 O1 C7 94.4(3) . . ?
O2 C1 N1 125.5(4) . . ?
O2 C1 C2 125.0(4) . . ?
N1 C1 C2 109.5(4) . . ?
C1 C2 C3 117.5(4) . . ?
C1 C2 C7 100.6(3) . . ?
C3 C2 C7 102.3(3) . . ?
C1 C2 H2 111.8 . . ?
C3 C2 H2 111.8 . . ?
C7 C2 H2 111.8 . . ?
C4 C3 C2 99.2(3) . . ?
C4 C3 H3A 111.9 . . ?
C2 C3 H3A 111.9 . . ?
C4 C3 H3B 111.9 . . ?
C2 C3 H3B 111.9 . . ?
H3A C3 H3B 109.6 . . ?
O1 C4 C5 102.4(3) . . ?
O1 C4 C3 101.7(3) . . ?
C5 C4 C3 110.4(4) . . ?
O1 C4 Br1 110.2(3) . . ?
C5 C4 Br1 115.4(3) . . ?
C3 C4 Br1 115.0(3) . . ?
C6 C5 C4 105.0(4) . . ?
C6 C5 H5 127.5 . . ?
C4 C5 H5 127.5 . . ?
C5 C6 C7 105.8(4) . . ?
C5 C6 H6 127.1 . . ?
C7 C6 H6 127.1 . . ?
O1 C7 C8 111.1(3) . . ?
O1 C7 C6 100.9(3) . . ?
C8 C7 C6 127.2(4) . . ?
O1 C7 C2 99.2(3) . . ?
C8 C7 C2 106.0(3) . . ?
C6 C7 C2 108.9(4) . . ?
N1 C8 C7 102.9(3) . . ?
N1 C8 H8A 111.2 . . ?
C7 C8 H8A 111.2 . . ?
N1 C8 H8B 111.2 . . ?
C7 C8 H8B 111.2 . . ?
H8A C8 H8B 109.1 . . ?
C14 C9 C10 119.2(4) . . ?
C14 C9 N1 121.9(4) . . ?
C10 C9 N1 119.0(4) . . ?
C11 C10 C9 119.6(4) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C12 C11 C10 121.8(4) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 118.3(4) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
C12 C13 C14 121.2(4) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C13 C14 C9 120.0(4) . . ?
C13 C14 H14 120.0 . . ?
C9 C14 H14 120.0 . . ?

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
C9 N1 C1 O2 6.4(7) . . . . ?
C8 N1 C1 O2 -171.1(4) . . . . ?
C9 N1 C1 C2 -172.5(4) . . . . ?
C8 N1 C1 C2 10.0(4) . . . . ?
O2 C1 C2 C3 46.6(6) . . . . ?
N1 C1 C2 C3 -134.5(4) . . . . ?
O2 C1 C2 C7 156.6(4) . . . . ?
N1 C1 C2 C7 -24.5(4) . . . . ?
C1 C2 C3 C4 109.8(4) . . . . ?
C7 C2 C3 C4 0.8(5) . . . . ?
C7 O1 C4 C5 -51.6(4) . . . . ?
C7 O1 C4 C3 62.6(4) . . . . ?
C7 O1 C4 Br1 -175.0(3) . . . . ?
C2 C3 C4 O1 -38.7(4) . . . . ?
C2 C3 C4 C5 69.5(5) . . . . ?
C2 C3 C4 Br1 -157.8(3) . . . . ?
O1 C4 C5 C6 33.4(5) . . . . ?
C3 C4 C5 C6 -74.3(5) . . . . ?
Br1 C4 C5 C6 153.2(3) . . . . ?
C4 C5 C6 C7 0.6(5) . . . . ?
C4 O1 C7 C8 -171.4(3) . . . . ?
C4 O1 C7 C6 51.3(3) . . . . ?
C4 O1 C7 C2 -60.1(3) . . . . ?
C5 C6 C7 O1 -33.5(4) . . . . ?
C5 C6 C7 C8 -160.9(4) . . . . ?
C5 C6 C7 C2 70.3(5) . . . . ?
C1 C2 C7 O1 -85.3(3) . . . . ?
C3 C2 C7 O1 36.1(4) . . . . ?
C1 C2 C7 C8 29.9(4) . . . . ?
C3 C2 C7 C8 151.3(4) . . . . ?
C1 C2 C7 C6 169.7(3) . . . . ?
C3 C2 C7 C6 -68.9(5) . . . . ?
C1 N1 C8 C7 9.7(4) . . . . ?
C9 N1 C8 C7 -167.9(3) . . . . ?
O1 C7 C8 N1 82.0(3) . . . . ?
C6 C7 C8 N1 -154.7(4) . . . . ?
C2 C7 C8 N1 -24.8(4) . . . . ?
C1 N1 C9 C14 8.4(6) . . . . ?
C8 N1 C9 C14 -174.3(4) . . . . ?
C1 N1 C9 C10 -171.6(4) . . . . ?
C8 N1 C9 C10 5.7(5) . . . . ?
C14 C9 C10 C11 -1.2(6) . . . . ?
N1 C9 C10 C11 178.7(4) . . . . ?
C9 C10 C11 C12 0.0(7) . . . . ?
C10 C11 C12 C13 1.1(7) . . . . ?
C11 C12 C13 C14 -1.0(7) . . . . ?
C12 C13 C14 C9 -0.3(7) . . . . ?
C10 C9 C14 C13 1.4(6) . . . . ?
N1 C9 C14 C13 -178.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.069
