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

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

data_202007111
_audit_block_doi                 10.5517/ccdc.csd.cc25t63b
_database_code_depnum_ccdc_archive 'CCDC 2020211'
loop_
_audit_author_name
_audit_author_address
'wenxue Duan'
;Zhengzhou University
China
;
_audit_update_record             
;
2020-07-30 deposited with the CCDC.	2021-01-11 downloaded from the CCDC.
;
_audit_creation_date             2020-07-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H6 F N O3'
_chemical_formula_sum            'C12 H6 F N O3'
_chemical_formula_weight         231.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H15N2O4F1
_chemical_oxdiff_usercomment     r
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   4.7015(6)
_cell_length_b                   7.5668(9)
_cell_length_c                   13.7164(15)
_cell_angle_alpha                100.964(10)
_cell_angle_beta                 91.553(10)
_cell_angle_gamma                102.630(10)
_cell_volume                     466.26(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    758
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.5180
_cell_measurement_theta_min      6.1030
_shelx_estimated_absorpt_T_max   0.866
_shelx_estimated_absorpt_T_min   0.821
_exptl_absorpt_coefficient_mu    1.143
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3316
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.057
_diffrn_reflns_theta_max         67.057
_diffrn_reflns_theta_min         6.118
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00  36.00   1.00    1.00    --  -33.50  77.00-150.00   98
  2  ω   -102.00 -15.00   1.00    1.00    --  -33.50 -57.00  90.00   87
  3  ω   -102.00 -15.00   1.00    1.00    --  -33.50 -57.00   0.00   87
  4  ω      8.00 106.00   1.00    1.00    --   36.47  77.00 -60.00   98
  5  ω     -4.00  77.00   1.00    1.00    --   36.47 -99.00  90.00   81
  6  ω     57.00 110.00   1.00    1.00    --   36.47 178.00 -30.00   53
  7  ω     14.00 107.00   1.00    1.00    --   36.47  37.00-150.00   93
  8  ω     57.00 110.00   1.00    1.00    --   36.47 178.00 120.00   53
  9  ω     57.00 110.00   1.00    1.00    --   36.47 178.00  60.00   53
 10  ω     57.00 110.00   1.00    1.00    --   36.47 178.00 150.00   53
 11  ω     37.00 112.00   1.00    2.50    --  108.00-111.00 -90.00   75
 12  ω     38.00 110.00   1.00    2.50    --  108.00 -94.00 150.00   72
 13  ω    100.00 178.00   1.00    2.50    --  108.00 111.00 -60.00   78
 14  ω     38.00 110.00   1.00    2.50    --  108.00 -94.00  60.00   72
 15  ω     37.00 112.00   1.00    2.50    --  108.00-111.00   0.00   75
 16  ω     38.00 128.00   1.00    2.50    --  108.00 -45.00 150.00   90
 17  ω     88.00 176.00   1.00    2.50    --  108.00  61.00  60.00   88
 18  ω     40.00 128.00   1.00    2.50    --  108.00 -61.00 -90.00   88
 19  ω     38.00 128.00   1.00    2.50    --  108.00 -45.00   0.00   90
 20  ω     82.00 178.00   1.00    2.50    --  108.00  30.00 120.00   96
 21  ω     83.00 175.00   1.00    2.50    --  108.00  30.00  30.00   92
;
_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      -0.1134091000
_diffrn_orient_matrix_UB_12      -0.0025024000
_diffrn_orient_matrix_UB_13      -0.1068006000
_diffrn_orient_matrix_UB_21      0.0388920000
_diffrn_orient_matrix_UB_22      0.2115142000
_diffrn_orient_matrix_UB_23      0.0258356000
_diffrn_orient_matrix_UB_31      0.3145941000
_diffrn_orient_matrix_UB_32      0.0249319000
_diffrn_orient_matrix_UB_33      -0.0328936000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1137
_reflns_number_total             1667
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1667
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.037
_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)+(0.0727P)²+0.0049P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1430
_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:
 C4(H4), C9(H9), C10(H10), C11(H11), C12(H12)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.5753(3) 0.3084(2) 0.66545(9) 0.0492(4) Uani 1 1 d . . . . .
O1 O 0.8945(4) 0.4700(3) 0.84000(12) 0.0493(5) Uani 1 1 d . . . . .
H1 H 0.9673 0.5037 0.8974 0.074 Uiso 1 1 calc GR . . . .
O2 O 0.7101(4) 0.3542(3) 1.00811(12) 0.0552(5) Uani 1 1 d . . . . .
O3 O -0.1204(3) -0.0586(2) 0.83722(11) 0.0416(4) Uani 1 1 d . . . . .
N1 N 0.0672(4) 0.0530(3) 0.66002(13) 0.0362(5) Uani 1 1 d . . . . .
C1 C 0.4870(5) 0.2621(3) 0.75142(17) 0.0365(5) Uani 1 1 d . . . . .
C2 C 0.6475(5) 0.3412(3) 0.83716(17) 0.0382(5) Uani 1 1 d . . . . .
C3 C 0.5537(5) 0.2839(3) 0.93096(17) 0.0423(6) Uani 1 1 d . . . . .
C4 C 0.2878(5) 0.1457(4) 0.92645(17) 0.0441(6) Uani 1 1 d . . . . .
H4 H 0.2238 0.1074 0.9842 0.053 Uiso 1 1 calc R . . . .
C5 C 0.1311(5) 0.0713(3) 0.83946(16) 0.0370(5) Uani 1 1 d . . . . .
C6 C 0.2176(4) 0.1241(3) 0.74492(16) 0.0332(5) Uani 1 1 d . . . . .
C7 C -0.1879(5) -0.0801(3) 0.66054(16) 0.0356(5) Uani 1 1 d . . . . .
C8 C -0.2813(5) -0.1366(3) 0.74797(16) 0.0355(5) Uani 1 1 d . . . . .
C9 C -0.5357(5) -0.2678(3) 0.74936(18) 0.0408(6) Uani 1 1 d . . . . .
H9 H -0.5961 -0.3016 0.8085 0.049 Uiso 1 1 calc R . . . .
C10 C -0.6974(5) -0.3472(3) 0.66039(19) 0.0451(6) Uani 1 1 d . . . . .
H10 H -0.8689 -0.4365 0.6595 0.054 Uiso 1 1 calc R . . . .
C11 C -0.6091(5) -0.2964(3) 0.57245(18) 0.0476(6) Uani 1 1 d . . . . .
H11 H -0.7208 -0.3524 0.5132 0.057 Uiso 1 1 calc R . . . .
C12 C -0.3574(5) -0.1637(4) 0.57169(17) 0.0425(6) Uani 1 1 d . . . . .
H12 H -0.3002 -0.1297 0.5122 0.051 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
F1 C1 1.344(2) . ?
O1 H1 0.8200 . ?
O1 C2 1.338(2) . ?
O2 C3 1.231(3) . ?
O3 C5 1.357(3) . ?
O3 C8 1.378(3) . ?
N1 C6 1.302(3) . ?
N1 C7 1.388(3) . ?
C1 C2 1.341(3) . ?
C1 C6 1.443(3) . ?
C2 C3 1.482(3) . ?
C3 C4 1.435(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.341(3) . ?
C5 C6 1.470(3) . ?
C7 C8 1.398(3) . ?
C7 C12 1.398(3) . ?
C8 C9 1.380(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.378(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.382(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(3) . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.5 . . ?
C5 O3 C8 119.63(17) . . ?
C6 N1 C7 117.11(18) . . ?
F1 C1 C6 116.42(19) . . ?
C2 C1 F1 120.30(19) . . ?
C2 C1 C6 123.3(2) . . ?
O1 C2 C1 121.3(2) . . ?
O1 C2 C3 118.8(2) . . ?
C1 C2 C3 119.8(2) . . ?
O2 C3 C2 118.5(2) . . ?
O2 C3 C4 123.4(2) . . ?
C4 C3 C2 118.0(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.8 . . ?
O3 C5 C6 117.59(19) . . ?
C4 C5 O3 119.3(2) . . ?
C4 C5 C6 123.1(2) . . ?
N1 C6 C1 121.00(19) . . ?
N1 C6 C5 123.67(19) . . ?
C1 C6 C5 115.33(19) . . ?
N1 C7 C8 121.9(2) . . ?
N1 C7 C12 120.01(19) . . ?
C12 C7 C8 118.1(2) . . ?
O3 C8 C7 120.07(19) . . ?
O3 C8 C9 117.6(2) . . ?
C9 C8 C7 122.3(2) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 C8 118.0(2) . . ?
C10 C9 H9 121.0 . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.1(2) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.7(2) . . ?
C12 C11 H11 119.7 . . ?
C7 C12 H12 120.1 . . ?
C11 C12 C7 119.8(2) . . ?
C11 C12 H12 120.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.82 1.95 2.687(2) 149.8 2_767

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
F1 C1 C2 O1 1.4(4) . . . . ?
F1 C1 C2 C3 -177.7(2) . . . . ?
F1 C1 C6 N1 -1.6(3) . . . . ?
F1 C1 C6 C5 178.00(19) . . . . ?
O1 C2 C3 O2 -1.5(4) . . . . ?
O1 C2 C3 C4 179.9(2) . . . . ?
O2 C3 C4 C5 -178.3(3) . . . . ?
O3 C5 C6 N1 -0.2(3) . . . . ?
O3 C5 C6 C1 -179.8(2) . . . . ?
O3 C8 C9 C10 -179.7(2) . . . . ?
N1 C7 C8 O3 0.6(4) . . . . ?
N1 C7 C8 C9 179.5(2) . . . . ?
N1 C7 C12 C11 179.6(2) . . . . ?
C1 C2 C3 O2 177.6(2) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C2 C1 C6 N1 179.0(2) . . . . ?
C2 C1 C6 C5 -1.4(3) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C3 C4 C5 O3 -179.7(2) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 N1 -179.9(2) . . . . ?
C4 C5 C6 C1 0.5(4) . . . . ?
C5 O3 C8 C7 -0.9(3) . . . . ?
C5 O3 C8 C9 -179.9(2) . . . . ?
C6 N1 C7 C8 -0.1(3) . . . . ?
C6 N1 C7 C12 -179.1(2) . . . . ?
C6 C1 C2 O1 -179.3(2) . . . . ?
C6 C1 C2 C3 1.6(4) . . . . ?
C7 N1 C6 C1 179.4(2) . . . . ?
C7 N1 C6 C5 -0.1(3) . . . . ?
C7 C8 C9 C10 1.4(4) . . . . ?
C8 O3 C5 C4 -179.5(2) . . . . ?
C8 O3 C5 C6 0.7(3) . . . . ?
C8 C7 C12 C11 0.5(4) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
C9 C10 C11 C12 -0.5(4) . . . . ?
C10 C11 C12 C7 0.4(4) . . . . ?
C12 C7 C8 O3 179.7(2) . . . . ?
C12 C7 C8 C9 -1.4(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 1.142
_oxdiff_exptl_absorpt_empirical_full_min 0.843
####################################################################### 
# 
# 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_20200636
_database_code_depnum_ccdc_archive 'CCDC 2012640'
loop_
_audit_author_name
_audit_author_address
OONO
;the Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2020-06-28 deposited with the CCDC.	2021-01-11 downloaded from the CCDC.
;
_audit_creation_date             2020-06-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 H6 O S, C12 H6 F N O3'
_chemical_formula_sum            'C14 H12 F N O4 S'
_chemical_formula_weight         309.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4F1
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'
F F 0.0727 0.0534 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.1820(7)
_cell_length_b                   7.3430(7)
_cell_length_c                   15.4344(9)
_cell_angle_alpha                97.694(6)
_cell_angle_beta                 93.323(7)
_cell_angle_gamma                97.422(9)
_cell_volume                     686.48(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1538
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.8470
_cell_measurement_theta_min      5.7960
_shelx_estimated_absorpt_T_max   0.798
_shelx_estimated_absorpt_T_min   0.675
_exptl_absorpt_coefficient_mu    2.367
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4915
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.066
_diffrn_reflns_theta_max         67.066
_diffrn_reflns_theta_min         5.803
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00  38.00   1.00    1.00    --  -33.50   0.00 150.00  143
  2  ω    -56.00  37.00   1.00    1.00    --  -33.50  37.00-180.00   93
  3  ω   -104.00 -11.00   1.00    1.00    --  -33.50 -37.00   0.00   93
  4  ω     -4.00  77.00   1.00    1.00    --   36.47 -99.00-180.00   81
  5  ω     -4.00  77.00   1.00    1.00    --   36.47 -99.00 -30.00   81
  6  ω     57.00 110.00   1.00    1.00    --   36.47 178.00-180.00   53
  7  ω     57.00 110.00   1.00    1.00    --   36.47 178.00 -90.00   53
  8  ω     57.00 110.00   1.00    1.00    --   36.47 178.00 -30.00   53
  9  ω      8.00 106.00   1.00    1.00    --   36.47  77.00 -60.00   98
 10  ω     40.00 128.00   1.00    1.00    --  108.00 -61.00-120.00   88
 11  ω     37.00 134.00   1.00    1.00    --  108.00 -30.00  60.00   97
 12  ω    100.00 175.00   1.00    1.00    --  108.00 111.00  60.00   75
 13  ω     38.00 110.00   1.00    1.00    --  108.00 -45.00 -60.00   72
 14  ω     89.00 167.00   1.00    1.00    --  108.00  61.00-120.00   78
 15  ω     62.00 100.00   1.00    1.00    --  108.00 178.00 150.00   38
 16  ω     63.00 109.00   1.00    1.00    --  108.00 -94.00-180.00   46
 17  ω     72.00 112.00   1.00    1.00    --  108.00-111.00 -60.00   40
 18  ω     40.00 112.00   1.00    1.00    --  108.00-111.00 120.00   72
 19  ω     42.00  89.00   1.00    1.00    --  108.00 -77.00 120.00   47
 20  ω    107.00 158.00   1.00    1.00    --  108.00  61.00   0.00   51
 21  ω     39.00 122.00   1.00    1.00    --  108.00 -45.00 150.00   83
 22  ω    103.00 147.00   1.00    1.00    --  108.00 178.00 150.00   44
 23  ω     82.00 171.00   1.00    1.00    --  108.00  30.00 -30.00   89
;
_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      0.1642834000
_diffrn_orient_matrix_UB_12      0.1768710000
_diffrn_orient_matrix_UB_13      0.0295784000
_diffrn_orient_matrix_UB_21      0.1907966000
_diffrn_orient_matrix_UB_22      -0.1152545000
_diffrn_orient_matrix_UB_23      -0.0093837000
_diffrn_orient_matrix_UB_31      0.0116386000
_diffrn_orient_matrix_UB_32      0.0335934000
_diffrn_orient_matrix_UB_33      -0.0961329000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1884
_reflns_number_total             2450
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0095(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2450
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.044
_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)+(0.0551P)²+0.1130P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1235
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3A), C4(H4), C12(H12)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.32583(12) 0.66151(9) 0.98988(4) 0.0540(2) Uani 1 1 d . . . . .
F1 F -0.2371(2) 0.2373(2) 0.70974(9) 0.0566(4) Uani 1 1 d . . . . .
O1 O -0.1944(3) 0.1871(2) 0.53591(10) 0.0443(4) Uani 1 1 d . . . . .
O2 O 0.0993(3) 0.4219(3) 0.82087(11) 0.0590(5) Uani 1 1 d . . . . .
O3 O 0.4889(3) 0.5701(3) 0.76201(11) 0.0547(5) Uani 1 1 d . . . . .
H3 H 0.4422 0.5948 0.8102 0.082 Uiso 1 1 calc GR . . . .
O4 O 0.4588(3) 0.7380(3) 0.92124(11) 0.0652(6) Uani 1 1 d . . . . .
N1 N 0.2093(3) 0.3243(3) 0.47450(12) 0.0432(5) Uani 1 1 d . . . . .
C1 C -0.3368(4) 0.0709(4) 0.39099(16) 0.0492(6) Uani 1 1 d . . . . .
H1 H -0.4686 0.0274 0.4121 0.059 Uiso 1 1 calc R . . . .
C2 C -0.3093(5) 0.0464(4) 0.30282(16) 0.0538(7) Uani 1 1 d . . . . .
H2 H -0.4249 -0.0136 0.2638 0.065 Uiso 1 1 calc R . . . .
C3 C -0.1126(5) 0.1094(4) 0.27074(16) 0.0529(7) Uani 1 1 d . . . . .
H3A H -0.0966 0.0904 0.2108 0.064 Uiso 1 1 calc R . . . .
C4 C 0.0591(4) 0.2000(4) 0.32770(16) 0.0496(6) Uani 1 1 d . . . . .
H4 H 0.1911 0.2420 0.3062 0.060 Uiso 1 1 calc R . . . .
C5 C 0.0354(4) 0.2290(3) 0.41791(15) 0.0411(6) Uani 1 1 d . . . . .
C6 C -0.1638(4) 0.1617(3) 0.44739(14) 0.0410(6) Uani 1 1 d . . . . .
C7 C 0.1799(4) 0.3486(3) 0.55783(14) 0.0391(5) Uani 1 1 d . . . . .
C8 C -0.0268(4) 0.2796(3) 0.59219(14) 0.0385(5) Uani 1 1 d . . . . .
C9 C -0.0496(4) 0.3055(3) 0.67817(15) 0.0427(6) Uani 1 1 d . . . . .
C10 C 0.1208(4) 0.4029(3) 0.74209(15) 0.0436(6) Uani 1 1 d . . . . .
C11 C 0.3267(4) 0.4772(3) 0.70565(15) 0.0428(6) Uani 1 1 d . . . . .
C12 C 0.3514(4) 0.4484(3) 0.61913(15) 0.0445(6) Uani 1 1 d . . . . .
H12 H 0.4830 0.4944 0.5986 0.053 Uiso 1 1 calc R . . . .
C13 C 0.0849(6) 0.7666(5) 0.9888(2) 0.0881(11) Uani 1 1 d . . . . .
H13A H 0.1226 0.8987 0.9930 0.132 Uiso 1 1 calc GR . . . .
H13B H 0.0040 0.7378 1.0376 0.132 Uiso 1 1 calc GR . . . .
H13C H -0.0030 0.7206 0.9351 0.132 Uiso 1 1 calc GR . . . .
C14 C 0.4516(6) 0.7797(5) 1.09170(17) 0.0745(10) Uani 1 1 d . . . . .
H14A H 0.5927 0.7419 1.1019 0.112 Uiso 1 1 calc GR . . . .
H14B H 0.3618 0.7502 1.1380 0.112 Uiso 1 1 calc GR . . . .
H14C H 0.4682 0.9111 1.0904 0.112 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O4 1.5014(19) . ?
S1 C13 1.764(3) . ?
S1 C14 1.774(3) . ?
F1 C9 1.347(3) . ?
O1 C6 1.381(3) . ?
O1 C8 1.359(3) . ?
O2 C10 1.222(3) . ?
O3 H3 0.8200 . ?
O3 C11 1.338(3) . ?
N1 C5 1.393(3) . ?
N1 C7 1.301(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.372(3) . ?
C1 C6 1.378(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(4) . ?
C3 H3A 0.9300 . ?
C3 C4 1.377(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.399(3) . ?
C5 C6 1.391(3) . ?
C7 C8 1.468(3) . ?
C7 C12 1.433(3) . ?
C8 C9 1.333(3) . ?
C9 C10 1.446(3) . ?
C10 C11 1.490(3) . ?
C11 C12 1.345(3) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 S1 C13 105.91(14) . . ?
O4 S1 C14 105.45(14) . . ?
C13 S1 C14 98.25(18) . . ?
C8 O1 C6 118.34(18) . . ?
C11 O3 H3 109.5 . . ?
C7 N1 C5 117.3(2) . . ?
C2 C1 H1 120.9 . . ?
C2 C1 C6 118.3(2) . . ?
C6 C1 H1 120.9 . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.3(2) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3A 120.0 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.1(2) . . ?
C5 C4 H4 119.9 . . ?
N1 C5 C4 119.4(2) . . ?
C6 C5 N1 122.5(2) . . ?
C6 C5 C4 118.1(2) . . ?
O1 C6 C5 120.0(2) . . ?
C1 C6 O1 117.7(2) . . ?
C1 C6 C5 122.3(2) . . ?
N1 C7 C8 122.1(2) . . ?
N1 C7 C12 119.9(2) . . ?
C12 C7 C8 117.9(2) . . ?
O1 C8 C7 119.6(2) . . ?
C9 C8 O1 120.1(2) . . ?
C9 C8 C7 120.3(2) . . ?
F1 C9 C10 116.5(2) . . ?
C8 C9 F1 120.2(2) . . ?
C8 C9 C10 123.3(2) . . ?
O2 C10 C9 122.6(2) . . ?
O2 C10 C11 121.9(2) . . ?
C9 C10 C11 115.5(2) . . ?
O3 C11 C10 117.9(2) . . ?
O3 C11 C12 120.8(2) . . ?
C12 C11 C10 121.2(2) . . ?
C7 C12 H12 119.2 . . ?
C11 C12 C7 121.7(2) . . ?
C11 C12 H12 119.2 . . ?
S1 C13 H13A 109.5 . . ?
S1 C13 H13B 109.5 . . ?
S1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
S1 C14 H14A 109.5 . . ?
S1 C14 H14B 109.5 . . ?
S1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C9 C10 O2 0.8(4) . . . . ?
F1 C9 C10 C11 -179.9(2) . . . . ?
O1 C8 C9 F1 1.2(4) . . . . ?
O1 C8 C9 C10 -179.8(2) . . . . ?
O2 C10 C11 O3 -1.3(4) . . . . ?
O2 C10 C11 C12 177.1(3) . . . . ?
O3 C11 C12 C7 179.7(2) . . . . ?
N1 C5 C6 O1 -0.5(4) . . . . ?
N1 C5 C6 C1 178.6(2) . . . . ?
N1 C7 C8 O1 0.0(4) . . . . ?
N1 C7 C8 C9 179.2(2) . . . . ?
N1 C7 C12 C11 179.6(2) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
C2 C1 C6 O1 179.4(2) . . . . ?
C2 C1 C6 C5 0.2(4) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C3 C4 C5 N1 -178.7(2) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C4 C5 C6 O1 180.0(2) . . . . ?
C4 C5 C6 C1 -0.9(4) . . . . ?
C5 N1 C7 C8 0.0(4) . . . . ?
C5 N1 C7 C12 -178.9(2) . . . . ?
C6 O1 C8 C7 -0.2(3) . . . . ?
C6 O1 C8 C9 -179.5(2) . . . . ?
C6 C1 C2 C3 0.6(4) . . . . ?
C7 N1 C5 C4 179.8(2) . . . . ?
C7 N1 C5 C6 0.3(4) . . . . ?
C7 C8 C9 F1 -178.1(2) . . . . ?
C7 C8 C9 C10 0.9(4) . . . . ?
C8 O1 C6 C1 -178.8(2) . . . . ?
C8 O1 C6 C5 0.5(3) . . . . ?
C8 C7 C12 C11 0.7(4) . . . . ?
C8 C9 C10 O2 -178.3(2) . . . . ?
C8 C9 C10 C11 1.0(4) . . . . ?
C9 C10 C11 O3 179.4(2) . . . . ?
C9 C10 C11 C12 -2.2(4) . . . . ?
C10 C11 C12 C7 1.4(4) . . . . ?
C12 C7 C8 O1 178.9(2) . . . . ?
C12 C7 C8 C9 -1.9(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 1.735
_oxdiff_exptl_absorpt_empirical_full_min 0.863
####################################################################### 
# 
# 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 
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data_202007112
_audit_block_doi                 10.5517/ccdc.csd.cc25t64c
_database_code_depnum_ccdc_archive 'CCDC 2020212'
loop_
_audit_author_name
_audit_author_address
'wenxue Duan'
;Zhengzhou University
China
;
_audit_update_record             
;
2020-07-30 deposited with the CCDC.	2021-01-11 downloaded from the CCDC.
;
_audit_creation_date             2020-07-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 N O4'
_chemical_formula_sum            'C13 H9 N O4'
_chemical_formula_weight         243.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H15N2O4
_chemical_oxdiff_usercomment     r
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   28.1572(5)
_cell_length_b                   11.7989(2)
_cell_length_c                   6.85220(14)
_cell_angle_alpha                90
_cell_angle_beta                 107.682(2)
_cell_angle_gamma                90
_cell_volume                     2168.92(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2207
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7590
_cell_measurement_theta_min      4.0740
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.871
_exptl_absorpt_coefficient_mu    0.946
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71318
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            6615
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.069
_diffrn_reflns_theta_max         67.068
_diffrn_reflns_theta_min         3.295
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00 -11.00   0.50    4.00    --  -33.50 -37.00 -90.00  186
  2  ω   -108.00 -32.00   0.50    4.00    --  -33.50 178.00  30.00  152
  3  ω    -71.00  39.00   0.50    4.00    --  -33.50  19.00  90.00  220
  4  ω     30.00 103.00   0.50    4.00    --   36.47-143.00 144.00  146
  5  ω      8.00 106.00   0.50    4.00    --   36.47  77.00   0.00  196
  6  ω     18.00 105.00   0.50    4.00    --   36.47  57.00-180.00  174
  7  ω     -4.00  77.00   0.50    4.00    --   36.47 -99.00 -60.00  162
  8  ω     -4.00  77.00   0.50    4.00    --   36.47 -99.00-180.00  162
  9  ω     57.00 110.00   0.50    4.00    --   36.47 178.00 -30.00  106
 10  ω     57.00 110.00   0.50    4.00    --   36.47 178.00   0.00  106
 11  ω     63.00 178.00   0.50   13.00    --  108.00  15.00-120.00  230
 12  ω     38.00  64.00   0.50   13.00    --  108.00-111.00-150.00   52
 13  ω     37.00 112.00   0.50   13.00    --  108.00-111.00 120.00  150
 14  ω     89.00 172.00   0.50   13.00    --  108.00  61.00 -60.00  166
 15  ω     66.00 110.00   0.50   13.00    --  108.00 -94.00 -60.00   88
 16  ω     38.00 108.00   0.50   13.00    --  108.00 -45.00-120.00  140
 17  ω     58.00 108.00   0.50   13.00    --  108.00-111.00 -90.00  100
 18  ω    110.00 171.00   0.50   13.00    --  108.00 111.00 -90.00  122
 19  ω     40.00 126.00   0.50   13.00    --  108.00 -45.00 -60.00  172
 20  ω     83.00 141.00   0.50   13.00    --  108.00  30.00  30.00  116
 21  ω     66.00  92.00   0.50   13.00    --  108.00-111.00-150.00   52
 22  ω    100.00 137.50   0.50   13.00    --  108.00 111.00-120.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0568185000
_diffrn_orient_matrix_UB_12      -0.0179017000
_diffrn_orient_matrix_UB_13      -0.0602745000
_diffrn_orient_matrix_UB_21      0.0076692500
_diffrn_orient_matrix_UB_22      -0.1290811500
_diffrn_orient_matrix_UB_23      -0.0066251000
_diffrn_orient_matrix_UB_31      0.0032555500
_diffrn_orient_matrix_UB_32      -0.0085289500
_diffrn_orient_matrix_UB_33      0.2280058000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1430
_reflns_number_total             1928
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.00033(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         1928
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0559P)²+0.5077P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1211
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C9(H9), C10(H10), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.47433(5) 0.17822(13) 0.4821(3) 0.0694(5) Uani 1 1 d . . . . .
H1 H 0.4770 0.1090 0.4814 0.104 Uiso 1 1 calc GR . . . .
O2 O 0.55493(5) 0.04371(13) 0.5525(2) 0.0626(4) Uani 1 1 d . . . . .
O3 O 0.65183(4) 0.12609(12) 0.6217(2) 0.0545(4) Uani 1 1 d . . . . .
O4 O 0.66316(4) 0.35269(11) 0.61730(19) 0.0476(4) Uani 1 1 d . . . . .
N1 N 0.57950(5) 0.49626(15) 0.5546(2) 0.0485(4) Uani 1 1 d . . . . .
C1 C 0.52573(7) 0.33837(19) 0.5208(3) 0.0543(5) Uani 1 1 d . . . . .
H1A H 0.4983 0.3857 0.5019 0.065 Uiso 1 1 calc R . . . .
C2 C 0.51954(7) 0.22568(19) 0.5168(3) 0.0522(5) Uani 1 1 d . . . . .
C3 C 0.56205(7) 0.14652(17) 0.5507(3) 0.0483(5) Uani 1 1 d . . . . .
C4 C 0.61112(6) 0.19560(17) 0.5818(3) 0.0461(5) Uani 1 1 d . . . . .
C5 C 0.61653(6) 0.30895(17) 0.5841(3) 0.0429(4) Uani 1 1 d . . . . .
C6 C 0.57433(6) 0.38658(17) 0.5538(3) 0.0453(5) Uani 1 1 d . . . . .
C7 C 0.62730(6) 0.53909(18) 0.5873(3) 0.0452(4) Uani 1 1 d . . . . .
C8 C 0.66861(7) 0.46821(17) 0.6198(3) 0.0447(4) Uani 1 1 d . . . . .
C9 C 0.71609(7) 0.5109(2) 0.6555(3) 0.0534(5) Uani 1 1 d . . . . .
H9 H 0.7432 0.4624 0.6776 0.064 Uiso 1 1 calc R . . . .
C10 C 0.72273(7) 0.6268(2) 0.6579(3) 0.0612(6) Uani 1 1 d . . . . .
H10 H 0.7546 0.6568 0.6822 0.073 Uiso 1 1 calc R . . . .
C11 C 0.68206(8) 0.6989(2) 0.6241(3) 0.0620(6) Uani 1 1 d . . . . .
H11 H 0.6868 0.7769 0.6246 0.074 Uiso 1 1 calc R . . . .
C12 C 0.63477(8) 0.65617(18) 0.5900(3) 0.0549(5) Uani 1 1 d . . . . .
H12 H 0.6078 0.7052 0.5688 0.066 Uiso 1 1 calc R . . . .
C13 C 0.65246(8) 0.0523(2) 0.4570(3) 0.0677(6) Uani 1 1 d . . . . .
H13A H 0.6456 0.0951 0.3324 0.102 Uiso 1 1 calc GR . . . .
H13B H 0.6276 -0.0054 0.4418 0.102 Uiso 1 1 calc GR . . . .
H13C H 0.6847 0.0175 0.4861 0.102 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8200 . ?
O1 C2 1.344(2) . ?
O2 C3 1.230(3) . ?
O3 C4 1.368(2) . ?
O3 C13 1.430(3) . ?
O4 C5 1.364(2) . ?
O4 C8 1.371(2) . ?
N1 C6 1.302(3) . ?
N1 C7 1.391(2) . ?
C1 H1A 0.9300 . ?
C1 C2 1.340(3) . ?
C1 C6 1.435(3) . ?
C2 C3 1.480(3) . ?
C3 C4 1.453(2) . ?
C4 C5 1.346(3) . ?
C5 C6 1.464(2) . ?
C7 C8 1.395(3) . ?
C7 C12 1.397(3) . ?
C8 C9 1.380(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.388(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(3) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.5 . . ?
C4 O3 C13 114.69(15) . . ?
C5 O4 C8 118.46(14) . . ?
C6 N1 C7 117.59(16) . . ?
C2 C1 H1A 119.7 . . ?
C2 C1 C6 120.55(18) . . ?
C6 C1 H1A 119.7 . . ?
O1 C2 C3 116.25(19) . . ?
C1 C2 O1 121.81(18) . . ?
C1 C2 C3 121.94(17) . . ?
O2 C3 C2 119.82(17) . . ?
O2 C3 C4 122.84(17) . . ?
C4 C3 C2 117.34(18) . . ?
O3 C4 C3 119.48(17) . . ?
C5 C4 O3 120.57(16) . . ?
C5 C4 C3 119.81(16) . . ?
O4 C5 C6 119.05(17) . . ?
C4 C5 O4 118.54(16) . . ?
C4 C5 C6 122.41(16) . . ?
N1 C6 C1 119.64(17) . . ?
N1 C6 C5 122.44(17) . . ?
C1 C6 C5 117.92(18) . . ?
N1 C7 C8 121.83(19) . . ?
N1 C7 C12 119.75(18) . . ?
C8 C7 C12 118.42(17) . . ?
O4 C8 C7 120.62(16) . . ?
O4 C8 C9 117.67(18) . . ?
C9 C8 C7 121.7(2) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 C8 119.0(2) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.22(19) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.7(2) . . ?
C12 C11 H11 119.6 . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 119.9(2) . . ?
C11 C12 H12 120.0 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.82 2.00 2.734(2) 149.5 5_656

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
O1 C2 C3 O2 -2.3(3) . . . . ?
O1 C2 C3 C4 177.98(18) . . . . ?
O2 C3 C4 O3 -2.3(3) . . . . ?
O2 C3 C4 C5 -177.99(19) . . . . ?
O3 C4 C5 O4 3.1(3) . . . . ?
O3 C4 C5 C6 -176.46(15) . . . . ?
O4 C5 C6 N1 0.9(3) . . . . ?
O4 C5 C6 C1 -179.53(16) . . . . ?
O4 C8 C9 C10 179.68(17) . . . . ?
N1 C7 C8 O4 1.0(3) . . . . ?
N1 C7 C8 C9 -178.95(17) . . . . ?
N1 C7 C12 C11 179.43(17) . . . . ?
C1 C2 C3 O2 177.6(2) . . . . ?
C1 C2 C3 C4 -2.1(3) . . . . ?
C2 C1 C6 N1 179.2(2) . . . . ?
C2 C1 C6 C5 -0.4(3) . . . . ?
C2 C3 C4 O3 177.44(16) . . . . ?
C2 C3 C4 C5 1.7(3) . . . . ?
C3 C4 C5 O4 178.83(15) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C4 C5 C6 N1 -179.51(18) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C5 O4 C8 C7 -0.6(2) . . . . ?
C5 O4 C8 C9 179.40(15) . . . . ?
C6 N1 C7 C8 -0.5(3) . . . . ?
C6 N1 C7 C12 -179.86(17) . . . . ?
C6 C1 C2 O1 -178.62(19) . . . . ?
C6 C1 C2 C3 1.5(3) . . . . ?
C7 N1 C6 C1 179.96(16) . . . . ?
C7 N1 C6 C5 -0.5(3) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
C8 O4 C5 C4 -179.95(16) . . . . ?
C8 O4 C5 C6 -0.3(2) . . . . ?
C8 C7 C12 C11 0.0(3) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C10 C11 C12 C7 -0.6(3) . . . . ?
C12 C7 C8 O4 -179.59(16) . . . . ?
C12 C7 C8 C9 0.5(3) . . . . ?
C13 O3 C4 C3 65.8(2) . . . . ?
C13 O3 C4 C5 -118.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.622
_oxdiff_exptl_absorpt_empirical_full_min 0.850
####################################################################### 
# 
# 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_20200639
_database_code_depnum_ccdc_archive 'CCDC 2012643'
loop_
_audit_author_name
_audit_author_address
OONO
;the Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2020-06-28 deposited with the CCDC.	2021-01-11 downloaded from the CCDC.
;
_audit_creation_date             2020-06-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 F N O3'
_chemical_formula_sum            'C13 H8 F N O3'
_chemical_formula_weight         245.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4F1
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.7844(15)
_cell_length_b                   7.8633(12)
_cell_length_c                   9.9225(18)
_cell_angle_alpha                71.839(15)
_cell_angle_beta                 82.190(16)
_cell_angle_gamma                67.855(16)
_cell_volume                     534.43(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    724
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5660
_cell_measurement_theta_min      4.6820
_shelx_estimated_absorpt_T_max   0.922
_shelx_estimated_absorpt_T_min   0.844
_exptl_absorpt_coefficient_mu    1.032
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3771
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.067
_diffrn_reflns_theta_max         67.067
_diffrn_reflns_theta_min         4.691
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00  -5.00   1.00    3.00    --  -33.50 -77.00-120.00   98
  2  ω    -71.00  39.00   1.00    3.00    --  -33.50  19.00  30.00  110
  3  ω    -52.00  35.00   1.00    3.00    --  -33.50  57.00  90.00   87
  4  ω     -4.00  77.00   1.00    3.00    --   36.47 -99.00  90.00   81
  5  ω     57.00 110.00   1.00    3.00    --   36.47 178.00 -90.00   53
  6  ω     57.00 110.00   1.00    3.00    --   36.47 178.00  90.00   53
  7  ω    -35.00 108.00   1.00    3.00    --   36.47   0.00-150.00  143
  8  ω     82.00 178.00   1.00    3.50    --  108.00  30.00 120.00   96
  9  ω     88.00 176.00   1.00    3.50    --  108.00  61.00  60.00   88
 10  ω     38.00 110.00   1.00    3.50    --  108.00 -94.00  30.00   72
 11  ω     37.00 112.00   1.00    3.50    --  108.00-111.00-120.00   75
 12  ω     40.00 128.00   1.00    3.50    --  108.00 -61.00-120.00   88
 13  ω     88.00 176.00   1.00    3.50    --  108.00  61.00 150.00   88
 14  ω     36.00 153.00   1.00    3.50    --  108.00 -15.00-120.00  117
 15  ω     38.00 110.00   1.00    3.50    --  108.00 -94.00-120.00   72
 16  ω    105.00 148.00   1.00    3.50    --  108.00 111.00-180.00   43
 17  ω     43.00 130.00   1.00    3.50    --  108.00 -30.00 120.00   87
 18  ω     79.00 110.00   1.00    3.50    --  108.00 -94.00 -90.00   31
 19  ω     87.00 127.00   1.00    3.50    --  108.00 -77.00  60.00   40
 20  ω     44.00 124.00   1.00    3.50    --  108.00 -61.00  30.00   80
;
_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      0.0990127000
_diffrn_orient_matrix_UB_12      -0.1998258000
_diffrn_orient_matrix_UB_13      -0.0226306000
_diffrn_orient_matrix_UB_21      -0.1350292000
_diffrn_orient_matrix_UB_22      0.0531524000
_diffrn_orient_matrix_UB_23      -0.1190460000
_diffrn_orient_matrix_UB_31      0.1328011000
_diffrn_orient_matrix_UB_32      0.0768500000
_diffrn_orient_matrix_UB_33      -0.1096664000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1239
_reflns_number_total             1910
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1910
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0509
_refine_ls_restrained_S_all      1.037
_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)+(0.0793P)²+0.0223P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1615
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3A), C4(H4), C12(H12)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.1479(2) -0.0329(2) 0.87315(17) 0.0844(6) Uani 1 1 d . . . . .
O1 O 0.3292(2) 0.3682(2) 0.46957(15) 0.0504(4) Uani 1 1 d . . . . .
O2 O 0.5063(2) 0.7846(2) 0.07466(15) 0.0577(5) Uani 1 1 d . . . . .
O3 O 0.3079(3) 1.0929(2) 0.16639(17) 0.0621(5) Uani 1 1 d . . . . .
H3 H 0.3702 1.0842 0.0936 0.093 Uiso 1 1 calc GR . . . .
N1 N 0.1213(3) 0.6892(3) 0.56747(19) 0.0516(5) Uani 1 1 d . . . . .
C1 C 0.2394(3) 0.1637(3) 0.6713(2) 0.0549(6) Uani 1 1 d . . . . .
H1 H 0.3085 0.0587 0.6383 0.066 Uiso 1 1 calc R . . . .
C2 C 0.1418(3) 0.1444(3) 0.7970(2) 0.0589(6) Uani 1 1 d . . . . .
C3 C 0.0376(3) 0.2963(4) 0.8502(3) 0.0623(7) Uani 1 1 d . . . . .
H3A H -0.0262 0.2765 0.9365 0.075 Uiso 1 1 calc R . . . .
C4 C 0.0304(3) 0.4772(4) 0.7726(2) 0.0592(6) Uani 1 1 d . . . . .
H4 H -0.0400 0.5813 0.8062 0.071 Uiso 1 1 calc R . . . .
C5 C 0.1280(3) 0.5061(3) 0.6434(2) 0.0493(6) Uani 1 1 d . . . . .
C6 C 0.2305(3) 0.3473(3) 0.5954(2) 0.0463(6) Uani 1 1 d . . . . .
C7 C 0.2173(3) 0.7089(3) 0.4487(2) 0.0453(5) Uani 1 1 d . . . . .
C8 C 0.3273(3) 0.5476(3) 0.3927(2) 0.0426(5) Uani 1 1 d . . . . .
C9 C 0.4246(3) 0.5649(3) 0.2692(2) 0.0441(5) Uani 1 1 d . . . . .
C10 C 0.4209(3) 0.7554(3) 0.1883(2) 0.0447(5) Uani 1 1 d . . . . .
C11 C 0.3099(3) 0.9187(3) 0.2444(2) 0.0473(5) Uani 1 1 d . . . . .
C12 C 0.2144(3) 0.8960(3) 0.3672(2) 0.0509(6) Uani 1 1 d . . . . .
H12 H 0.1461 1.0016 0.3998 0.061 Uiso 1 1 calc R . . . .
C13 C 0.5310(4) 0.3987(3) 0.2113(2) 0.0616(7) Uani 1 1 d . . . . .
H13A H 0.5911 0.2886 0.2874 0.092 Uiso 1 1 calc GR . . . .
H13B H 0.6226 0.4300 0.1434 0.092 Uiso 1 1 calc GR . . . .
H13C H 0.4474 0.3709 0.1660 0.092 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.349(2) . ?
O1 C6 1.373(2) . ?
O1 C8 1.375(2) . ?
O2 C10 1.231(2) . ?
O3 H3 0.8200 . ?
O3 C11 1.343(2) . ?
N1 C5 1.386(3) . ?
N1 C7 1.306(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.367(3) . ?
C1 C6 1.384(3) . ?
C2 C3 1.381(4) . ?
C3 H3A 0.9300 . ?
C3 C4 1.374(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.398(3) . ?
C5 C6 1.393(3) . ?
C7 C8 1.463(3) . ?
C7 C12 1.434(3) . ?
C8 C9 1.347(3) . ?
C9 C10 1.454(3) . ?
C9 C13 1.499(3) . ?
C10 C11 1.478(3) . ?
C11 C12 1.337(3) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 C8 119.02(17) . . ?
C11 O3 H3 109.5 . . ?
C7 N1 C5 117.70(19) . . ?
C2 C1 H1 121.6 . . ?
C2 C1 C6 116.8(2) . . ?
C6 C1 H1 121.6 . . ?
F1 C2 C1 118.0(2) . . ?
F1 C2 C3 118.4(2) . . ?
C1 C2 C3 123.6(2) . . ?
C2 C3 H3A 120.7 . . ?
C4 C3 C2 118.5(2) . . ?
C4 C3 H3A 120.7 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
N1 C5 C4 119.8(2) . . ?
N1 C5 C6 122.0(2) . . ?
C6 C5 C4 118.2(2) . . ?
O1 C6 C1 117.3(2) . . ?
O1 C6 C5 120.38(19) . . ?
C1 C6 C5 122.4(2) . . ?
N1 C7 C8 122.83(19) . . ?
N1 C7 C12 119.40(19) . . ?
C12 C7 C8 117.76(19) . . ?
O1 C8 C7 118.08(18) . . ?
C9 C8 O1 118.01(18) . . ?
C9 C8 C7 123.90(19) . . ?
C8 C9 C10 117.63(19) . . ?
C8 C9 C13 123.03(19) . . ?
C10 C9 C13 119.33(19) . . ?
O2 C10 C9 122.10(19) . . ?
O2 C10 C11 119.27(18) . . ?
C9 C10 C11 118.63(18) . . ?
O3 C11 C10 117.14(18) . . ?
C12 C11 O3 120.84(19) . . ?
C12 C11 C10 122.02(19) . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 120.05(19) . . ?
C11 C12 H12 120.0 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O2 0.82 2.00 2.723(2) 146.1 2_675

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
F1 C2 C3 C4 -179.7(2) . . . . ?
O1 C8 C9 C10 179.65(17) . . . . ?
O1 C8 C9 C13 1.1(3) . . . . ?
O2 C10 C11 O3 0.3(3) . . . . ?
O2 C10 C11 C12 -179.9(2) . . . . ?
O3 C11 C12 C7 179.6(2) . . . . ?
N1 C5 C6 O1 0.0(4) . . . . ?
N1 C5 C6 C1 179.3(2) . . . . ?
N1 C7 C8 O1 -0.3(3) . . . . ?
N1 C7 C8 C9 178.6(2) . . . . ?
N1 C7 C12 C11 -179.0(2) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C1 C6 O1 179.5(2) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C3 C4 C5 N1 -179.1(2) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C4 C5 C6 O1 -179.7(2) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C5 N1 C7 C8 1.1(3) . . . . ?
C5 N1 C7 C12 -179.8(2) . . . . ?
C6 O1 C8 C7 -0.7(3) . . . . ?
C6 O1 C8 C9 -179.72(18) . . . . ?
C6 C1 C2 F1 180.0(2) . . . . ?
C6 C1 C2 C3 -0.1(4) . . . . ?
C7 N1 C5 C4 178.7(2) . . . . ?
C7 N1 C5 C6 -1.0(3) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C7 C8 C9 C13 -177.8(2) . . . . ?
C8 O1 C6 C1 -178.53(18) . . . . ?
C8 O1 C6 C5 0.9(3) . . . . ?
C8 C7 C12 C11 0.1(3) . . . . ?
C8 C9 C10 O2 179.6(2) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C9 C10 C11 O3 -179.32(19) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 C11 C12 C7 -0.1(4) . . . . ?
C12 C7 C8 O1 -179.34(18) . . . . ?
C12 C7 C8 C9 -0.4(3) . . . . ?
C13 C9 C10 O2 -1.8(3) . . . . ?
C13 C9 C10 C11 177.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.396
_oxdiff_exptl_absorpt_empirical_full_min 0.828
####################################################################### 
# 
# 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_20200638
_database_code_depnum_ccdc_archive 'CCDC 2012642'
loop_
_audit_author_name
_audit_author_address
OONO
;the Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2020-06-28 deposited with the CCDC.	2021-01-11 downloaded from the CCDC.
;
_audit_creation_date             2020-06-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H11 N O3'
_chemical_formula_sum            'C14 H11 N O3'
_chemical_formula_weight         241.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4Cl1
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                   4.6906(3)
_cell_length_b                   14.7537(9)
_cell_length_c                   16.5416(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.187(6)
_cell_angle_gamma                90
_cell_volume                     1135.74(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    701
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.9800
_cell_measurement_theta_min      4.0090
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.879
_exptl_absorpt_coefficient_mu    0.828
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10259
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4088
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.067
_diffrn_reflns_theta_max         67.067
_diffrn_reflns_theta_min         4.029
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -15.00   1.00    4.00    --  -33.50 -57.00 -90.00   87
  2  ω   -108.00 -32.00   1.00    4.00    --  -33.50 178.00  90.00   76
  3  ω     44.00  69.00   1.00    4.00    --   36.47 -19.00  30.00   25
  4  ω     59.00  91.00   1.00    4.00    --   36.47 178.00-120.00   32
  5  ω     79.00 109.00   1.00    4.00    --   36.47 178.00-180.00   30
  6  ω     57.00  86.00   1.00    4.00    --   36.47-142.00 111.00   29
  7  ω     76.00 106.00   1.00    4.00    --   36.47 178.00  30.00   30
  8  ω    -36.00  23.00   1.00    4.00    --   36.47 -19.00  30.00   59
  9  ω     39.00 119.00   1.00    7.50    --  108.00 -45.00-150.00   80
 10  ω     55.00 106.00   1.00    7.50    --  108.00-111.00 150.00   51
 11  ω     44.00 128.00   1.00    7.50    --  108.00 -45.00 120.00   84
 12  ω    104.00 149.00   1.00    7.50    --  108.00  45.00  30.00   45
 13  ω     49.00 104.00   1.00    7.50    --  108.00 -45.00  60.00   55
 14  ω     52.00 100.00   1.00    7.50    --  108.00-111.00  30.00   48
 15  ω     52.00 109.00   1.00    7.50    --  108.00 -94.00-150.00   57
 16  ω     82.00 158.00   1.00    7.50    --  108.00  30.00 -60.00   76
;
_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      0.0853924000
_diffrn_orient_matrix_UB_12      -0.0640786000
_diffrn_orient_matrix_UB_13      0.0726029000
_diffrn_orient_matrix_UB_21      0.0043544000
_diffrn_orient_matrix_UB_22      -0.0804814000
_diffrn_orient_matrix_UB_23      -0.0591917000
_diffrn_orient_matrix_UB_31      0.3195462000
_diffrn_orient_matrix_UB_32      0.0182174000
_diffrn_orient_matrix_UB_33      -0.0064075000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1192
_reflns_number_total             2025
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.124
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2025
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0590
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0724P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1356
_refine_ls_wR_factor_ref         0.1657
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3A), C12(H12)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7592(4) 0.68612(12) 0.22616(12) 0.0469(5) Uani 1 1 d . . . . .
O2 O 1.3558(5) 0.58474(14) 0.03798(12) 0.0570(6) Uani 1 1 d . . . . .
O3 O 1.2717(5) 0.41005(13) 0.07419(14) 0.0567(6) Uani 1 1 d . . . . .
H3 H 1.3763 0.4334 0.0438 0.085 Uiso 1 1 calc GR . . . .
N1 N 0.6770(5) 0.50346(15) 0.26782(14) 0.0420(6) Uani 1 1 d . . . . .
C1 C 0.4768(6) 0.7357(2) 0.32504(18) 0.0514(8) Uani 1 1 d . . . . .
H1 H 0.5097 0.7954 0.3108 0.062 Uiso 1 1 calc R . . . .
C2 C 0.3089(7) 0.7154(2) 0.38530(19) 0.0587(9) Uani 1 1 d . . . . .
H2 H 0.2277 0.7621 0.4125 0.070 Uiso 1 1 calc R . . . .
C3 C 0.2598(7) 0.6260(2) 0.40584(18) 0.0546(8) Uani 1 1 d . . . . .
H3A H 0.1439 0.6141 0.4463 0.066 Uiso 1 1 calc R . . . .
C4 C 0.3779(6) 0.5541(2) 0.36792(17) 0.0461(7) Uani 1 1 d . . . . .
C5 C 0.5518(6) 0.57357(17) 0.30646(16) 0.0411(7) Uani 1 1 d . . . . .
C6 C 0.5946(6) 0.66425(19) 0.28659(16) 0.0413(7) Uani 1 1 d . . . . .
C7 C 0.8393(5) 0.52469(18) 0.21166(16) 0.0398(6) Uani 1 1 d . . . . .
C8 C 0.8883(6) 0.61842(17) 0.18820(16) 0.0395(6) Uani 1 1 d . . . . .
C9 C 1.0530(6) 0.64123(19) 0.12988(16) 0.0416(6) Uani 1 1 d . . . . .
C10 C 1.1929(6) 0.57027(19) 0.08989(16) 0.0425(7) Uani 1 1 d . . . . .
C11 C 1.1432(6) 0.47526(19) 0.11329(17) 0.0428(7) Uani 1 1 d . . . . .
C12 C 0.9741(6) 0.45457(18) 0.17091(17) 0.0454(7) Uani 1 1 d . . . . .
H12 H 0.9453 0.3943 0.1841 0.054 Uiso 1 1 calc R . . . .
C13 C 0.3243(7) 0.4575(2) 0.39070(19) 0.0606(9) Uani 1 1 d . . . . .
H13A H 0.2099 0.4279 0.3462 0.091 Uiso 1 1 calc GR . . . .
H13B H 0.2243 0.4564 0.4379 0.091 Uiso 1 1 calc GR . . . .
H13C H 0.5046 0.4264 0.4026 0.091 Uiso 1 1 calc GR . . . .
C14 C 1.0973(8) 0.7381(2) 0.1053(2) 0.0648(10) Uani 1 1 d . . . . .
H14A H 0.9512 0.7546 0.0619 0.097 Uiso 1 1 calc GR . . . .
H14B H 1.2830 0.7441 0.0871 0.097 Uiso 1 1 calc GR . . . .
H14C H 1.0859 0.7772 0.1511 0.097 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.376(3) . ?
O1 C8 1.361(3) . ?
O2 C10 1.237(3) . ?
O3 H3 0.8200 . ?
O3 C11 1.344(3) . ?
N1 C5 1.385(3) . ?
N1 C7 1.310(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.379(4) . ?
C1 C6 1.382(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(4) . ?
C3 H3A 0.9300 . ?
C3 C4 1.383(4) . ?
C4 C5 1.410(4) . ?
C4 C13 1.504(4) . ?
C5 C6 1.398(4) . ?
C7 C8 1.462(4) . ?
C7 C12 1.425(4) . ?
C8 C9 1.352(4) . ?
C9 C10 1.440(4) . ?
C9 C14 1.507(4) . ?
C10 C11 1.480(4) . ?
C11 C12 1.349(4) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C6 119.0(2) . . ?
C11 O3 H3 109.5 . . ?
C7 N1 C5 117.8(2) . . ?
C2 C1 H1 121.2 . . ?
C2 C1 C6 117.7(3) . . ?
C6 C1 H1 121.2 . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.7(3) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3A 119.0 . . ?
C4 C3 C2 121.9(3) . . ?
C4 C3 H3A 119.0 . . ?
C3 C4 C5 118.2(3) . . ?
C3 C4 C13 121.6(3) . . ?
C5 C4 C13 120.2(3) . . ?
N1 C5 C4 119.9(2) . . ?
N1 C5 C6 121.6(2) . . ?
C6 C5 C4 118.5(2) . . ?
O1 C6 C1 116.6(2) . . ?
O1 C6 C5 120.4(2) . . ?
C1 C6 C5 123.0(2) . . ?
N1 C7 C8 122.6(2) . . ?
N1 C7 C12 119.6(3) . . ?
C12 C7 C8 117.8(2) . . ?
O1 C8 C7 118.5(2) . . ?
C9 C8 O1 118.3(2) . . ?
C9 C8 C7 123.2(2) . . ?
C8 C9 C10 118.8(3) . . ?
C8 C9 C14 122.6(3) . . ?
C10 C9 C14 118.6(2) . . ?
O2 C10 C9 123.4(3) . . ?
O2 C10 C11 118.4(3) . . ?
C9 C10 C11 118.2(2) . . ?
O3 C11 C10 117.2(2) . . ?
O3 C11 C12 121.1(3) . . ?
C12 C11 C10 121.7(2) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.3(3) . . ?
C11 C12 H12 119.8 . . ?
C4 C13 H13A 109.5 . . ?
C4 C13 H13B 109.5 . . ?
C4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O2 0.82 1.98 2.704(3) 147.4 3_865

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
O1 C8 C9 C10 179.4(2) . . . . ?
O1 C8 C9 C14 -0.3(4) . . . . ?
O2 C10 C11 O3 -2.3(4) . . . . ?
O2 C10 C11 C12 178.3(3) . . . . ?
O3 C11 C12 C7 -179.9(3) . . . . ?
N1 C5 C6 O1 1.4(4) . . . . ?
N1 C5 C6 C1 -178.8(3) . . . . ?
N1 C7 C8 O1 -0.2(4) . . . . ?
N1 C7 C8 C9 -179.4(3) . . . . ?
N1 C7 C12 C11 -179.6(3) . . . . ?
C1 C2 C3 C4 0.7(5) . . . . ?
C2 C1 C6 O1 179.4(3) . . . . ?
C2 C1 C6 C5 -0.3(5) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C2 C3 C4 C13 179.8(3) . . . . ?
C3 C4 C5 N1 179.1(3) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C4 C5 C6 O1 -179.0(2) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?
C5 N1 C7 C8 -0.8(4) . . . . ?
C5 N1 C7 C12 179.5(2) . . . . ?
C6 O1 C8 C7 1.8(3) . . . . ?
C6 O1 C8 C9 -179.0(3) . . . . ?
C6 C1 C2 C3 -0.4(5) . . . . ?
C7 N1 C5 C4 -179.3(3) . . . . ?
C7 N1 C5 C6 0.2(4) . . . . ?
C7 C8 C9 C10 -1.4(4) . . . . ?
C7 C8 C9 C14 178.9(3) . . . . ?
C8 O1 C6 C1 177.8(3) . . . . ?
C8 O1 C6 C5 -2.4(4) . . . . ?
C8 C7 C12 C11 0.7(4) . . . . ?
C8 C9 C10 O2 -177.3(3) . . . . ?
C8 C9 C10 C11 1.5(4) . . . . ?
C9 C10 C11 O3 178.9(2) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C10 C11 C12 C7 -0.5(4) . . . . ?
C12 C7 C8 O1 179.5(2) . . . . ?
C12 C7 C8 C9 0.3(4) . . . . ?
C13 C4 C5 N1 -1.0(4) . . . . ?
C13 C4 C5 C6 179.5(3) . . . . ?
C14 C9 C10 O2 2.4(4) . . . . ?
C14 C9 C10 C11 -178.8(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 7.202
_oxdiff_exptl_absorpt_empirical_full_min 0.724
####################################################################### 
# 
# 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_20200427
_database_code_depnum_ccdc_archive 'CCDC 2012644'
loop_
_audit_author_name
_audit_author_address
OONO
;the Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2020-06-28 deposited with the CCDC.	2021-01-11 downloaded from the CCDC.
;
_audit_creation_date             2020-04-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 Br N O3'
_chemical_formula_sum            'C13 H8 Br N O3'
_chemical_formula_weight         306.11
_chemical_melting_point          ?
_chemical_oxdiff_formula         C40H40O4Cl1Br1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   4.70525(16)
_cell_length_b                   13.1424(4)
_cell_length_c                   18.3356(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.343(3)
_cell_angle_gamma                90
_cell_volume                     1126.90(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1656
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3190
_cell_measurement_theta_min      4.1330
_shelx_estimated_absorpt_T_max   0.865
_shelx_estimated_absorpt_T_min   0.435
_exptl_absorpt_coefficient_mu    4.990
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.804
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4063
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.061
_diffrn_reflns_theta_max         67.061
_diffrn_reflns_theta_min         4.147
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00  37.00   1.00    2.50    --  -33.50  37.00 -30.00   93
  2  ω   -102.00 -15.00   1.00    2.50    --  -33.50 -57.00-180.00   87
  3  ω     18.00 105.00   1.00    2.50    --   36.47  57.00  30.00   87
  4  ω    -33.00  65.00   1.00    2.50    --   36.47 -77.00  60.00   98
  5  ω     66.00 106.00   1.00    2.50    --   36.47 178.00 -90.00   40
  6  ω     69.00  94.00   1.00    2.50    --   36.47-141.00 137.00   25
  7  ω    101.00 127.00   1.00    8.00    --  108.00 111.00-150.00   26
  8  ω     43.00 110.00   1.00    8.00    --  108.00-111.00-150.00   67
  9  ω    144.00 178.00   1.00    8.00    --  108.00 124.00 116.00   34
 10  ω     37.00 131.00   1.00    8.00    --  108.00 -30.00  30.00   94
 11  ω    100.00 126.00   1.00    8.00    --  108.00 124.00 116.00   26
 12  ω     39.00 127.00   1.00    8.00    --  108.00 -45.00 -60.00   88
 13  ω     62.00 109.00   1.00    8.00    --  108.00 -94.00-120.00   47
 14  ω     64.00 159.00   1.00    8.00    --  108.00  15.00  60.00   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      0.0604649000
_diffrn_orient_matrix_UB_12      -0.0253304000
_diffrn_orient_matrix_UB_13      0.0822715000
_diffrn_orient_matrix_UB_21      0.0245428000
_diffrn_orient_matrix_UB_22      -0.1136960000
_diffrn_orient_matrix_UB_23      -0.0188677000
_diffrn_orient_matrix_UB_31      0.3228663000
_diffrn_orient_matrix_UB_32      0.0134251000
_diffrn_orient_matrix_UB_33      -0.0044365000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1670
_reflns_number_total             2011
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2011
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0495
_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)+(0.0817P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1420
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C9(H9)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.43111(10) 0.33914(4) 0.43786(2) 0.0520(2) Uani 1 1 d . . . . .
O1 O 0.1737(6) 0.3983(2) 0.22197(15) 0.0386(6) Uani 1 1 d . . . . .
O2 O 0.9215(7) 0.6251(3) 0.0786(2) 0.0528(8) Uani 1 1 d . . . . .
H2 H 1.0188 0.5854 0.0575 0.079 Uiso 1 1 calc GR . . . .
O3 O 0.7727(6) 0.4343(3) 0.03591(16) 0.0496(8) Uani 1 1 d . . . . .
N1 N 0.3294(7) 0.5977(3) 0.26810(18) 0.0383(7) Uani 1 1 d . . . . .
C1 C -0.1051(8) 0.3797(3) 0.3203(2) 0.0377(8) Uani 1 1 d . . . . .
H1 H -0.1555 0.3143 0.3044 0.045 Uiso 1 1 calc R . . . .
C2 C -0.2045(8) 0.4204(3) 0.3821(2) 0.0388(9) Uani 1 1 d . . . . .
C3 C -0.1354(9) 0.5190(3) 0.4057(2) 0.0431(9) Uani 1 1 d . . . . .
H3 H -0.2083 0.5453 0.4469 0.052 Uiso 1 1 calc R . . . .
C4 C 0.0400(9) 0.5767(4) 0.3679(2) 0.0448(10) Uani 1 1 d . . . . .
H4 H 0.0881 0.6423 0.3839 0.054 Uiso 1 1 calc R . . . .
C5 C 0.1488(8) 0.5385(3) 0.3052(2) 0.0352(8) Uani 1 1 d . . . . .
C6 C 0.0712(8) 0.4394(3) 0.2831(2) 0.0346(8) Uani 1 1 d . . . . .
C7 C 0.3598(7) 0.4535(3) 0.1856(2) 0.0333(8) Uani 1 1 d . . . . .
C8 C 0.4337(8) 0.5567(3) 0.2119(2) 0.0352(8) Uani 1 1 d . . . . .
C9 C 0.6296(8) 0.6137(3) 0.1735(2) 0.0407(9) Uani 1 1 d . . . . .
H9 H 0.6817 0.6792 0.1889 0.049 Uiso 1 1 calc R . . . .
C10 C 0.7394(8) 0.5730(3) 0.1148(2) 0.0403(9) Uani 1 1 d . . . . .
C11 C 0.6630(8) 0.4685(3) 0.0893(2) 0.0383(9) Uani 1 1 d . . . . .
C12 C 0.4659(8) 0.4103(3) 0.1277(2) 0.0359(8) Uani 1 1 d . . . . .
C13 C 0.3856(10) 0.3042(3) 0.1025(3) 0.0487(10) Uani 1 1 d . . . . .
H13A H 0.3981 0.2594 0.1441 0.073 Uiso 1 1 calc GR . . . .
H13B H 0.5140 0.2813 0.0687 0.073 Uiso 1 1 calc GR . . . .
H13C H 0.1934 0.3040 0.0786 0.073 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2 1.888(4) . ?
O1 C6 1.378(5) . ?
O1 C7 1.366(5) . ?
O2 H2 0.8200 . ?
O2 C10 1.329(5) . ?
O3 C11 1.241(5) . ?
N1 C5 1.385(5) . ?
N1 C8 1.307(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.381(5) . ?
C1 C6 1.377(6) . ?
C2 C3 1.393(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.365(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.402(6) . ?
C5 C6 1.400(6) . ?
C7 C8 1.468(6) . ?
C7 C12 1.348(5) . ?
C8 C9 1.432(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.353(6) . ?
C10 C11 1.482(6) . ?
C11 C12 1.444(6) . ?
C12 C13 1.504(6) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C6 119.3(3) . . ?
C10 O2 H2 109.5 . . ?
C8 N1 C5 117.4(3) . . ?
C2 C1 H1 121.2 . . ?
C6 C1 H1 121.2 . . ?
C6 C1 C2 117.6(4) . . ?
C1 C2 Br1 119.2(3) . . ?
C1 C2 C3 121.8(4) . . ?
C3 C2 Br1 119.0(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.5(4) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.9(4) . . ?
C5 C4 H4 119.6 . . ?
N1 C5 C4 120.1(4) . . ?
N1 C5 C6 122.3(4) . . ?
C6 C5 C4 117.6(4) . . ?
O1 C6 C5 119.8(3) . . ?
C1 C6 O1 117.6(3) . . ?
C1 C6 C5 122.6(4) . . ?
O1 C7 C8 118.1(3) . . ?
C12 C7 O1 118.3(3) . . ?
C12 C7 C8 123.6(4) . . ?
N1 C8 C7 122.9(4) . . ?
N1 C8 C9 119.4(4) . . ?
C9 C8 C7 117.7(3) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(4) . . ?
C10 C9 H9 119.8 . . ?
O2 C10 C9 121.1(4) . . ?
O2 C10 C11 117.8(4) . . ?
C9 C10 C11 121.1(4) . . ?
O3 C11 C10 118.5(4) . . ?
O3 C11 C12 122.5(4) . . ?
C12 C11 C10 119.0(3) . . ?
C7 C12 C11 118.3(4) . . ?
C7 C12 C13 122.0(4) . . ?
C11 C12 C13 119.7(4) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O3 0.82 2.08 2.785(5) 143.8 3_765

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C2 C3 C4 176.7(3) . . . . ?
O1 C7 C8 N1 -0.1(5) . . . . ?
O1 C7 C8 C9 179.8(3) . . . . ?
O1 C7 C12 C11 -179.9(3) . . . . ?
O1 C7 C12 C13 0.0(6) . . . . ?
O2 C10 C11 O3 0.3(6) . . . . ?
O2 C10 C11 C12 179.9(3) . . . . ?
O3 C11 C12 C7 179.3(4) . . . . ?
O3 C11 C12 C13 -0.5(6) . . . . ?
N1 C5 C6 O1 -0.6(5) . . . . ?
N1 C5 C6 C1 179.1(4) . . . . ?
N1 C8 C9 C10 -179.7(4) . . . . ?
C1 C2 C3 C4 -1.4(6) . . . . ?
C2 C1 C6 O1 179.1(3) . . . . ?
C2 C1 C6 C5 -0.6(6) . . . . ?
C2 C3 C4 C5 0.8(6) . . . . ?
C3 C4 C5 N1 -179.2(4) . . . . ?
C3 C4 C5 C6 -0.1(6) . . . . ?
C4 C5 C6 O1 -179.7(3) . . . . ?
C4 C5 C6 C1 0.0(6) . . . . ?
C5 N1 C8 C7 2.2(5) . . . . ?
C5 N1 C8 C9 -177.7(3) . . . . ?
C6 O1 C7 C8 -2.4(5) . . . . ?
C6 O1 C7 C12 177.5(3) . . . . ?
C6 C1 C2 Br1 -176.8(3) . . . . ?
C6 C1 C2 C3 1.3(6) . . . . ?
C7 O1 C6 C1 -177.0(3) . . . . ?
C7 O1 C6 C5 2.8(5) . . . . ?
C7 C8 C9 C10 0.4(6) . . . . ?
C8 N1 C5 C4 177.2(4) . . . . ?
C8 N1 C5 C6 -1.9(5) . . . . ?
C8 C7 C12 C11 0.0(5) . . . . ?
C8 C7 C12 C13 179.8(4) . . . . ?
C8 C9 C10 O2 -180.0(4) . . . . ?
C8 C9 C10 C11 -0.7(6) . . . . ?
C9 C10 C11 O3 -179.0(4) . . . . ?
C9 C10 C11 C12 0.6(6) . . . . ?
C10 C11 C12 C7 -0.2(5) . . . . ?
C10 C11 C12 C13 179.9(4) . . . . ?
C12 C7 C8 N1 -180.0(4) . . . . ?
C12 C7 C8 C9 0.0(6) . . . . ?

_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 0.795
####################################################################### 
# 
# 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_20200637
_database_code_depnum_ccdc_archive 'CCDC 2012641'
loop_
_audit_author_name
_audit_author_address
OONO
;the Cambridge Crystallographic Data Centre
China
;
_audit_update_record             
;
2020-06-28 deposited with the CCDC.	2021-01-11 downloaded from the CCDC.
;
_audit_creation_date             2020-06-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H9 N O3'
_chemical_formula_sum            'C13 H9 N O3'
_chemical_formula_weight         227.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4Cl1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.6718(15)
_cell_length_b                   7.8925(13)
_cell_length_c                   10.0037(14)
_cell_angle_alpha                71.388(14)
_cell_angle_beta                 80.879(14)
_cell_angle_gamma                66.502(17)
_cell_volume                     526.10(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1036
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.2940
_cell_measurement_theta_min      4.6420
_shelx_estimated_absorpt_T_max   0.897
_shelx_estimated_absorpt_T_min   0.847
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3745
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         4.667
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -32.00   1.00    2.00    --  -33.50 178.00-150.00   76
  2  ω   -102.00 -15.00   1.00    2.00    --  -33.50 -57.00-180.00   87
  3  ω    -81.00  14.00   1.00    2.00    --  -33.50 112.00  -9.00   95
  4  ω   -108.00 -32.00   1.00    2.00    --  -33.50 178.00 150.00   76
  5  ω    -71.00  39.00   1.00    2.00    --  -33.50  19.00   0.00  110
  6  ω     14.00 107.00   1.00    2.00    --   36.47  37.00-180.00   93
  7  ω     -4.00  77.00   1.00    2.00    --   36.47 -99.00-180.00   81
  8  ω      8.00 106.00   1.00    2.00    --   36.47  77.00  60.00   98
  9  ω     57.00 110.00   1.00    2.00    --   36.47 178.00  30.00   53
 10  ω     38.00 110.00   1.00    2.50    --  108.00 -94.00 150.00   72
 11  ω     38.00 110.00   1.00    2.50    --  108.00 -94.00 -90.00   72
 12  ω     82.00 178.00   1.00    2.50    --  108.00  30.00 -30.00   96
 13  ω     38.00 128.00   1.00    2.50    --  108.00 -45.00 150.00   90
 14  ω     40.00 128.00   1.00    2.50    --  108.00 -61.00 -60.00   88
 15  ω    100.00 178.00   1.00    2.50    --  108.00 111.00 -60.00   78
 16  ω     96.00 133.00   1.00    2.50    --  108.00  77.00  90.00   37
 17  ω     52.00 119.00   1.00    2.50    --  108.00 -61.00-120.00   67
 18  ω     40.00 119.00   1.00    2.50    --  108.00 -45.00  30.00   79
 19  ω     63.00 107.00   1.00    2.50    --  108.00-111.00  90.00   44
 20  ω     79.00 105.00   1.00    2.50    --  108.00 -94.00 -30.00   26
 21  ω     90.00 177.00   1.00    2.50    --  108.00  30.00  60.00   87
 22  ω     88.00 155.00   1.00    2.50    --  108.00  61.00   0.00   67
;
_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      -0.1342119000
_diffrn_orient_matrix_UB_12      0.1314071000
_diffrn_orient_matrix_UB_13      0.0888879000
_diffrn_orient_matrix_UB_21      -0.0418556000
_diffrn_orient_matrix_UB_22      0.1741118000
_diffrn_orient_matrix_UB_23      -0.1327415000
_diffrn_orient_matrix_UB_31      -0.1680593000
_diffrn_orient_matrix_UB_32      -0.0406716000
_diffrn_orient_matrix_UB_33      -0.0303017000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1195
_reflns_number_total             1874
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0084(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1874
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.025
_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)+(0.0708P)²+0.0206P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1481
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3A), C4(H4), C12(H12)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3374(2) -0.13821(19) 0.46721(15) 0.0551(4) Uani 1 1 d . . . . .
O2 O 0.4964(2) 0.2869(2) 0.06719(14) 0.0639(5) Uani 1 1 d . . . . .
O3 O 0.3010(2) 0.59238(19) 0.16758(16) 0.0648(5) Uani 1 1 d . . . . .
H3 H 0.3673 0.5841 0.0953 0.097 Uiso 1 1 calc GR . . . .
N1 N 0.1206(3) 0.1815(3) 0.56981(19) 0.0556(5) Uani 1 1 d . . . . .
C1 C 0.2517(4) -0.3461(3) 0.6703(2) 0.0636(7) Uani 1 1 d . . . . .
H1 H 0.3235 -0.4499 0.6348 0.076 Uiso 1 1 calc R . . . .
C2 C 0.1559(4) -0.3729(4) 0.7995(3) 0.0712(7) Uani 1 1 d . . . . .
H2 H 0.1649 -0.4965 0.8525 0.085 Uiso 1 1 calc R . . . .
C3 C 0.0467(4) -0.2178(4) 0.8510(3) 0.0719(7) Uani 1 1 d . . . . .
H3A H -0.0184 -0.2381 0.9377 0.086 Uiso 1 1 calc R . . . .
C4 C 0.0332(3) -0.0343(4) 0.7755(2) 0.0656(7) Uani 1 1 d . . . . .
H4 H -0.0406 0.0689 0.8110 0.079 Uiso 1 1 calc R . . . .
C5 C 0.1307(3) -0.0030(3) 0.6450(2) 0.0532(5) Uani 1 1 d . . . . .
C6 C 0.2385(3) -0.1616(3) 0.5950(2) 0.0519(5) Uani 1 1 d . . . . .
C7 C 0.2170(3) 0.2028(3) 0.4496(2) 0.0485(5) Uani 1 1 d . . . . .
C8 C 0.3313(3) 0.0420(3) 0.3915(2) 0.0461(5) Uani 1 1 d . . . . .
C9 C 0.4282(3) 0.0615(3) 0.2665(2) 0.0470(5) Uani 1 1 d . . . . .
C10 C 0.4178(3) 0.2532(3) 0.1852(2) 0.0482(5) Uani 1 1 d . . . . .
C11 C 0.3064(3) 0.4167(3) 0.2447(2) 0.0495(5) Uani 1 1 d . . . . .
C12 C 0.2115(3) 0.3913(3) 0.3693(2) 0.0537(6) Uani 1 1 d . . . . .
H12 H 0.1418 0.4964 0.4039 0.064 Uiso 1 1 calc R . . . .
C13 C 0.5413(4) -0.1048(3) 0.2069(2) 0.0685(7) Uani 1 1 d . . . . .
H13A H 0.6239 -0.2076 0.2772 0.103 Uiso 1 1 calc GR . . . .
H13B H 0.6160 -0.0639 0.1260 0.103 Uiso 1 1 calc GR . . . .
H13C H 0.4563 -0.1490 0.1795 0.103 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.378(2) . ?
O1 C8 1.367(2) . ?
O2 C10 1.237(2) . ?
O3 H3 0.8200 . ?
O3 C11 1.342(2) . ?
N1 C5 1.386(3) . ?
N1 C7 1.307(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.380(3) . ?
C1 C6 1.380(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(4) . ?
C3 H3A 0.9300 . ?
C3 C4 1.373(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.399(3) . ?
C5 C6 1.394(3) . ?
C7 C8 1.463(3) . ?
C7 C12 1.435(3) . ?
C8 C9 1.346(3) . ?
C9 C10 1.448(3) . ?
C9 C13 1.502(3) . ?
C10 C11 1.483(3) . ?
C11 C12 1.339(3) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C6 119.10(17) . . ?
C11 O3 H3 109.5 . . ?
C7 N1 C5 117.74(19) . . ?
C2 C1 H1 120.8 . . ?
C2 C1 C6 118.4(2) . . ?
C6 C1 H1 120.8 . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.6(2) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3A 119.6 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.9(2) . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 120.1(2) . . ?
N1 C5 C6 121.7(2) . . ?
C6 C5 C4 118.2(2) . . ?
O1 C6 C1 117.5(2) . . ?
O1 C6 C5 120.39(18) . . ?
C1 C6 C5 122.1(2) . . ?
N1 C7 C8 122.94(18) . . ?
N1 C7 C12 119.4(2) . . ?
C12 C7 C8 117.65(19) . . ?
O1 C8 C7 118.08(18) . . ?
C9 C8 O1 118.06(18) . . ?
C9 C8 C7 123.85(18) . . ?
C8 C9 C10 117.85(19) . . ?
C8 C9 C13 123.09(18) . . ?
C10 C9 C13 119.05(18) . . ?
O2 C10 C9 122.75(19) . . ?
O2 C10 C11 118.44(18) . . ?
C9 C10 C11 118.81(18) . . ?
O3 C11 C10 117.46(18) . . ?
C12 C11 O3 121.03(19) . . ?
C12 C11 C10 121.50(18) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.3(2) . . ?
C11 C12 H12 119.8 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C8 C9 C10 178.62(16) . . . . ?
O1 C8 C9 C13 0.2(3) . . . . ?
O2 C10 C11 O3 -1.5(3) . . . . ?
O2 C10 C11 C12 177.3(2) . . . . ?
O3 C11 C12 C7 179.27(19) . . . . ?
N1 C5 C6 O1 -0.7(3) . . . . ?
N1 C5 C6 C1 178.9(2) . . . . ?
N1 C7 C8 O1 -0.3(3) . . . . ?
N1 C7 C8 C9 178.5(2) . . . . ?
N1 C7 C12 C11 -178.73(19) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C2 C1 C6 O1 179.10(19) . . . . ?
C2 C1 C6 C5 -0.6(3) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 N1 -178.7(2) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 O1 -179.88(18) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C5 N1 C7 C8 0.8(3) . . . . ?
C5 N1 C7 C12 -179.47(18) . . . . ?
C6 O1 C8 C7 -0.8(3) . . . . ?
C6 O1 C8 C9 -179.63(17) . . . . ?
C6 C1 C2 C3 1.1(4) . . . . ?
C7 N1 C5 C4 178.77(19) . . . . ?
C7 N1 C5 C6 -0.3(3) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C7 C8 C9 C13 -178.58(19) . . . . ?
C8 O1 C6 C1 -178.36(18) . . . . ?
C8 O1 C6 C5 1.3(3) . . . . ?
C8 C7 C12 C11 1.0(3) . . . . ?
C8 C9 C10 O2 -177.51(19) . . . . ?
C8 C9 C10 C11 1.6(3) . . . . ?
C9 C10 C11 O3 179.33(18) . . . . ?
C9 C10 C11 C12 -1.9(3) . . . . ?
C10 C11 C12 C7 0.5(3) . . . . ?
C12 C7 C8 O1 -179.97(17) . . . . ?
C12 C7 C8 C9 -1.2(3) . . . . ?
C13 C9 C10 O2 1.0(3) . . . . ?
C13 C9 C10 C11 -179.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.687
_oxdiff_exptl_absorpt_empirical_full_min 0.770
####################################################################### 
# 
# 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_202007123
_database_code_depnum_ccdc_archive 'CCDC 2023111'
loop_
_audit_author_name
_audit_author_address
'wenxue Duan'
;Zhengzhou University
China
;
_audit_update_record             
;
2020-08-13 deposited with the CCDC.	2021-01-11 downloaded from the CCDC.
;
_audit_creation_date             2020-07-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H11 N O5'
_chemical_formula_sum            'C14 H11 N O5'
_chemical_formula_weight         273.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H15N2O1
_chemical_oxdiff_usercomment     r
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   14.4314(8)
_cell_length_b                   4.4645(3)
_cell_length_c                   18.5538(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.744(5)
_cell_angle_gamma                90
_cell_volume                     1195.28(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    875
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.1820
_cell_measurement_theta_min      6.0980
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.827
_exptl_absorpt_coefficient_mu    0.990
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4371
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         3.856
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -15.00   0.50   12.50    --  -33.50 -57.00  90.00  174
  2  ω   -104.00 -11.00   0.50   12.50    --  -33.50 -37.00 -30.00  186
  3  ω     14.00 107.00   0.50   12.50    --   36.47  37.00 -60.00  186
  4  ω     14.00 107.00   0.50   12.50    --   36.47  37.00 -30.00  186
  5  ω     41.00 109.00   0.50   12.50    --   36.47  19.00-180.00  136
  6  ω     84.00 110.00   0.50   12.50    --   36.47 178.00 -60.00   52
  7  ω     20.00  60.00   0.50   12.50    --   36.47  57.00  60.00   80
  8  ω     80.00 105.00   0.50   12.50    --   36.47  57.00  60.00   50
  9  ω     82.00 108.00   0.50   12.50    --   36.47 178.00 -90.00   52
 10  ω     72.00 164.00   0.50   17.50    --  108.00  15.00 150.00  184
 11  ω     40.00 107.00   0.50   17.50    --  108.00 -94.00-180.00  134
 12  ω     41.00 107.00   0.50   17.50    --  108.00 -45.00 150.00  132
 13  ω    146.00 175.00   0.50   17.50    --  108.00 111.00  60.00   58
 14  ω     39.00  64.00   0.50   17.50    --  108.00-111.00 150.00   50
 15  ω    149.00 174.00   0.50   17.50    --  108.00 111.00 120.00   50
 16  ω     38.00 134.00   0.50   17.50    --  108.00 -30.00 -60.00  192
 17  ω    149.00 174.00   0.50   17.50    --  108.00  61.00 -60.00   50
 18  ω    109.00 135.00   0.50   17.50    --  108.00  61.00 -60.00   52
;
_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      -0.0000448000
_diffrn_orient_matrix_UB_12      -0.1035427000
_diffrn_orient_matrix_UB_13      0.0792158000
_diffrn_orient_matrix_UB_21      0.1065059000
_diffrn_orient_matrix_UB_22      0.0219568000
_diffrn_orient_matrix_UB_23      0.0027481000
_diffrn_orient_matrix_UB_31      -0.0071057000
_diffrn_orient_matrix_UB_32      0.3283983000
_diffrn_orient_matrix_UB_33      0.0248308000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1388
_reflns_number_total             2131
_reflns_odcompleteness_completeness 99.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.017
_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)+(0.0691P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1454
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C9(H9), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.44860(17) 0.3321(6) 0.24922(12) 0.0455(6) Uani 1 1 d . . . . .
C2 C 0.37752(17) 0.5450(6) 0.26834(13) 0.0455(6) Uani 1 1 d . . . . .
C3 C 0.37551(16) 0.6425(6) 0.34480(13) 0.0439(6) Uani 1 1 d . . . . .
C4 C 0.43447(16) 0.5311(6) 0.39500(12) 0.0431(6) Uani 1 1 d . . . . .
H4 H 0.4313 0.5975 0.4424 0.052 Uiso 1 1 calc R . . . .
C5 C 0.50181(16) 0.3117(5) 0.37569(12) 0.0412(6) Uani 1 1 d . . . . .
C6 C 0.50559(16) 0.2169(5) 0.29988(12) 0.0418(6) Uani 1 1 d . . . . .
C7 C 0.62893(17) -0.1026(5) 0.33268(12) 0.0435(6) Uani 1 1 d . . . . .
C8 C 0.62400(16) -0.0047(6) 0.40364(12) 0.0416(6) Uani 1 1 d . . . . .
C9 C 0.68732(17) -0.1172(6) 0.45488(13) 0.0473(6) Uani 1 1 d . . . . .
H9 H 0.6851 -0.0529 0.5025 0.057 Uiso 1 1 calc R . . . .
C10 C 0.75265(17) -0.3233(6) 0.43423(14) 0.0492(6) Uani 1 1 d . . . . .
C11 C 0.75479(18) -0.4241(6) 0.36237(14) 0.0522(7) Uani 1 1 d . . . . .
H11 H 0.7983 -0.5668 0.3491 0.063 Uiso 1 1 calc R . . . .
C12 C 0.69363(17) -0.3146(6) 0.31182(14) 0.0483(6) Uani 1 1 d . . . . .
H12 H 0.6954 -0.3811 0.2644 0.058 Uiso 1 1 calc R . . . .
C13 C 0.5139(2) 0.4253(8) 0.13672(15) 0.0731(9) Uani 1 1 d . . . . .
H13A H 0.5106 0.3641 0.0871 0.110 Uiso 1 1 calc GR . . . .
H13B H 0.5763 0.4038 0.1544 0.110 Uiso 1 1 calc GR . . . .
H13C H 0.4952 0.6309 0.1406 0.110 Uiso 1 1 calc GR . . . .
C14 C 0.8239(2) -0.3341(7) 0.55045(15) 0.0719(9) Uani 1 1 d . . . . .
H14A H 0.8360 -0.1227 0.5493 0.108 Uiso 1 1 calc GR . . . .
H14B H 0.8731 -0.4338 0.5761 0.108 Uiso 1 1 calc GR . . . .
H14C H 0.7663 -0.3701 0.5743 0.108 Uiso 1 1 calc GR . . . .
N1 N 0.55866(13) 0.2053(5) 0.42491(10) 0.0422(5) Uani 1 1 d . . . . .
O1 O 0.45363(13) 0.2422(5) 0.17836(9) 0.0608(6) Uani 1 1 d . . . . .
O2 O 0.32023(12) 0.6488(4) 0.22523(9) 0.0574(5) Uani 1 1 d . . . . .
O3 O 0.31146(12) 0.8464(4) 0.36208(9) 0.0548(5) Uani 1 1 d . . . . .
H3 H 0.2812 0.8916 0.3260 0.082 Uiso 1 1 calc GR . . . .
O4 O 0.56977(11) 0.0098(4) 0.28017(8) 0.0483(5) Uani 1 1 d . . . . .
O5 O 0.81826(13) -0.4469(5) 0.47829(10) 0.0651(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.446(3) . ?
C1 C6 1.343(3) . ?
C1 O1 1.377(3) . ?
C2 C3 1.485(3) . ?
C2 O2 1.233(3) . ?
C3 C4 1.348(3) . ?
C3 O3 1.339(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.429(3) . ?
C5 C6 1.471(3) . ?
C5 N1 1.309(3) . ?
C6 O4 1.362(3) . ?
C7 C8 1.390(3) . ?
C7 C12 1.388(3) . ?
C7 O4 1.381(3) . ?
C8 C9 1.403(3) . ?
C8 N1 1.390(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.375(3) . ?
C10 C11 1.408(4) . ?
C10 O5 1.360(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.370(3) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 O1 1.428(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14 O5 1.432(3) . ?
O3 H3 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.7(2) . . ?
C6 C1 O1 121.1(2) . . ?
O1 C1 C2 118.2(2) . . ?
C1 C2 C3 116.7(2) . . ?
O2 C2 C1 124.0(2) . . ?
O2 C2 C3 119.2(2) . . ?
C4 C3 C2 122.1(2) . . ?
O3 C3 C2 116.8(2) . . ?
O3 C3 C4 121.1(2) . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.3(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 118.1(2) . . ?
N1 C5 C4 119.7(2) . . ?
N1 C5 C6 122.1(2) . . ?
C1 C6 C5 121.9(2) . . ?
C1 C6 O4 119.0(2) . . ?
O4 C6 C5 119.1(2) . . ?
C12 C7 C8 121.4(2) . . ?
O4 C7 C8 121.0(2) . . ?
O4 C7 C12 117.6(2) . . ?
C7 C8 C9 119.2(2) . . ?
C7 C8 N1 121.6(2) . . ?
N1 C8 C9 119.2(2) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.6(2) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C11 120.1(2) . . ?
O5 C10 C9 125.4(2) . . ?
O5 C10 C11 114.6(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C7 C12 H12 120.6 . . ?
C11 C12 C7 118.8(2) . . ?
C11 C12 H12 120.6 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O5 C14 H14A 109.5 . . ?
O5 C14 H14B 109.5 . . ?
O5 C14 H14C 109.5 . . ?
C5 N1 C8 117.9(2) . . ?
C1 O1 C13 112.9(2) . . ?
C3 O3 H3 109.5 . . ?
C6 O4 C7 118.26(18) . . ?
C10 O5 C14 116.7(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O2 0.82 2.08 2.825(2) 150.8 2

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -2.4(4) . . . . ?
C1 C2 C3 O3 178.1(2) . . . . ?
C1 C6 O4 C7 178.9(2) . . . . ?
C2 C1 C6 C5 -3.2(4) . . . . ?
C2 C1 C6 O4 177.9(2) . . . . ?
C2 C1 O1 C13 90.8(3) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C3 C4 C5 N1 -180.0(2) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C4 C5 C6 O4 179.5(2) . . . . ?
C4 C5 N1 C8 -179.1(2) . . . . ?
C5 C6 O4 C7 -0.1(3) . . . . ?
C6 C1 C2 C3 4.0(3) . . . . ?
C6 C1 C2 O2 -176.5(2) . . . . ?
C6 C1 O1 C13 -91.8(3) . . . . ?
C6 C5 N1 C8 -0.2(3) . . . . ?
C7 C8 C9 C10 -0.4(4) . . . . ?
C7 C8 N1 C5 -0.6(3) . . . . ?
C8 C7 C12 C11 -1.3(4) . . . . ?
C8 C7 O4 C6 -0.8(3) . . . . ?
C8 C9 C10 C11 -1.1(4) . . . . ?
C8 C9 C10 O5 179.3(2) . . . . ?
C9 C8 N1 C5 178.5(2) . . . . ?
C9 C10 C11 C12 1.4(4) . . . . ?
C9 C10 O5 C14 -5.3(4) . . . . ?
C10 C11 C12 C7 -0.3(4) . . . . ?
C11 C10 O5 C14 175.1(2) . . . . ?
C12 C7 C8 C9 1.6(4) . . . . ?
C12 C7 C8 N1 -179.3(2) . . . . ?
C12 C7 O4 C6 179.7(2) . . . . ?
N1 C5 C6 C1 -178.4(2) . . . . ?
N1 C5 C6 O4 0.5(3) . . . . ?
N1 C8 C9 C10 -179.5(2) . . . . ?
O1 C1 C2 C3 -178.6(2) . . . . ?
O1 C1 C2 O2 0.9(4) . . . . ?
O1 C1 C6 C5 179.5(2) . . . . ?
O1 C1 C6 O4 0.6(4) . . . . ?
O2 C2 C3 C4 178.1(2) . . . . ?
O2 C2 C3 O3 -1.4(3) . . . . ?
O3 C3 C4 C5 179.4(2) . . . . ?
O4 C7 C8 C9 -178.0(2) . . . . ?
O4 C7 C8 N1 1.1(4) . . . . ?
O4 C7 C12 C11 178.3(2) . . . . ?
O5 C10 C11 C12 -178.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.166
_oxdiff_exptl_absorpt_empirical_full_min 0.853
