# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_my24_2
_audit_block_doi                 10.5517/ccdc.csd.cc1zwg6j
_database_code_depnum_ccdc_archive 'CCDC 1843638'
loop_
_audit_author_name
_audit_author_address
'Xiong-Li Liu'
;guizhou university
China
;
_audit_update_record             
;
2018-05-16 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;
_audit_creation_date             2017-11-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H17 N O4, H2 O'
_chemical_formula_sum            'C24 H19 N O5'
_chemical_formula_weight         401.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   28.3770(19)
_cell_length_b                   7.1579(5)
_cell_length_c                   19.4046(16)
_cell_angle_alpha                90
_cell_angle_beta                 103.671(7)
_cell_angle_gamma                90
_cell_volume                     3829.8(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3940
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      28.4780
_cell_measurement_theta_min      3.0660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1680
_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  0.0319
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10036
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.564
_diffrn_reflns_theta_min         2.160
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     71.00  97.00   1.00   12.00    --   11.74-178.00 150.00   26
  2  ω    -68.00  17.00   1.00   12.00    --   11.74 -19.00 120.00   85
  3  ω    -53.00  37.00   1.00   12.00    --   11.74 -19.00   0.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0206666000
_diffrn_orient_matrix_UB_12      -0.0532082000
_diffrn_orient_matrix_UB_13      0.0165983000
_diffrn_orient_matrix_UB_21      0.0015421000
_diffrn_orient_matrix_UB_22      0.0499845000
_diffrn_orient_matrix_UB_23      0.0320261000
_diffrn_orient_matrix_UB_31      -0.0152430000
_diffrn_orient_matrix_UB_32      -0.0669709000
_diffrn_orient_matrix_UB_33      0.0107225000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3446
_reflns_number_total             4532
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4532
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0515
_refine_ls_restrained_S_all      1.065
_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)+(0.0344P)²+3.3272P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1135
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB)
2.b Secondary CH2 refined with riding coordinates:
 C00H(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C7(H7), C12(H12), C2(H2), C14(H14), C13(H13), C18(H18), C5(H5),
 C4(H4), C3(H3A), C22(H22), C19(H19), C20(H20), C21(H21)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.62077(4) 0.70365(17) 0.56370(6) 0.0211(3) Uani 1 1 d . . . . .
O4 O 0.68029(4) 0.53096(17) 0.71224(6) 0.0211(3) Uani 1 1 d . . . . .
O3 O 0.70169(4) 0.13591(17) 0.67322(7) 0.0220(3) Uani 1 1 d . . . . .
H3 H 0.708695 0.052301 0.702759 0.033 Uiso 1 1 calc GR . . . .
O1W O 0.71732(4) -0.13051(17) 0.77129(7) 0.0244(3) Uani 1 1 d . . . . .
H1WA H 0.702772 -0.232897 0.758187 0.037 Uiso 1 1 d G . . . .
H1WB H 0.746826 -0.161449 0.786937 0.037 Uiso 1 1 d G . . . .
O2 O 0.70761(5) 0.36336(18) 0.47882(7) 0.0252(3) Uani 1 1 d . . . . .
N1 N 0.59714(5) 0.5066(2) 0.69369(7) 0.0181(3) Uani 1 1 d . . . . .
C8 C 0.65722(6) 0.4082(2) 0.56036(9) 0.0177(4) Uani 1 1 d . . . . .
C1 C 0.66963(6) 0.6635(2) 0.48110(9) 0.0188(4) Uani 1 1 d . . . . .
C15 C 0.55913(6) 0.4272(2) 0.64132(9) 0.0187(4) Uani 1 1 d . . . . .
C16 C 0.64144(6) 0.4699(2) 0.67933(9) 0.0177(4) Uani 1 1 d . . . . .
C00B C 0.64671(6) 0.6015(2) 0.53751(9) 0.0174(4) Uani 1 1 d . . . . .
C9 C 0.63344(6) 0.3325(2) 0.61656(9) 0.0175(4) Uani 1 1 d . . . . .
C10 C 0.57842(6) 0.3257(2) 0.59356(9) 0.0183(4) Uani 1 1 d . . . . .
C6 C 0.69890(6) 0.5428(2) 0.45389(9) 0.0210(4) Uani 1 1 d . . . . .
C17 C 0.58959(6) 0.6445(2) 0.74324(9) 0.0193(4) Uani 1 1 d . . . . .
C11 C 0.54796(6) 0.2338(2) 0.53801(9) 0.0214(4) Uani 1 1 d . . . . .
H11 H 0.560510 0.164037 0.506060 0.026 Uiso 1 1 calc R . . . .
C00H C 0.65091(6) 0.1379(2) 0.64511(10) 0.0202(4) Uani 1 1 d . . . . .
H00A H 0.634644 0.102536 0.681846 0.024 Uiso 1 1 calc R . . . .
H00B H 0.642472 0.047104 0.607080 0.024 Uiso 1 1 calc R . . . .
C7 C 0.68689(6) 0.3054(3) 0.53106(9) 0.0218(4) Uani 1 1 d . . . . .
H7 H 0.693758 0.184559 0.548071 0.026 Uiso 1 1 calc R . . . .
C12 C 0.49795(7) 0.2474(3) 0.53058(10) 0.0245(4) Uani 1 1 d . . . . .
H12 H 0.476925 0.187827 0.492944 0.029 Uiso 1 1 calc R . . . .
C2 C 0.66288(6) 0.8444(3) 0.45270(10) 0.0229(4) Uani 1 1 d . . . . .
H2 H 0.643065 0.927816 0.469460 0.028 Uiso 1 1 calc R . . . .
C14 C 0.50988(6) 0.4406(3) 0.63576(10) 0.0226(4) Uani 1 1 d . . . . .
H14 H 0.497479 0.507874 0.668502 0.027 Uiso 1 1 calc R . . . .
C13 C 0.47952(6) 0.3487(3) 0.57879(10) 0.0236(4) Uani 1 1 d . . . . .
H13 H 0.446100 0.355839 0.573172 0.028 Uiso 1 1 calc R . . . .
C18 C 0.60036(6) 0.6039(3) 0.81465(10) 0.0243(4) Uani 1 1 d . . . . .
H18 H 0.613704 0.488848 0.830982 0.029 Uiso 1 1 calc R . . . .
C5 C 0.72123(7) 0.5957(3) 0.40035(10) 0.0262(4) Uani 1 1 d . . . . .
H5 H 0.740415 0.511707 0.382603 0.031 Uiso 1 1 calc R . . . .
C4 C 0.71436(7) 0.7743(3) 0.37428(10) 0.0278(4) Uani 1 1 d . . . . .
H4 H 0.729318 0.812134 0.338823 0.033 Uiso 1 1 calc R . . . .
C3 C 0.68519(7) 0.9001(3) 0.40035(10) 0.0272(4) Uani 1 1 d . . . . .
H3A H 0.680839 1.021010 0.382424 0.033 Uiso 1 1 calc R . . . .
C22 C 0.57023(7) 0.8158(3) 0.71824(10) 0.0261(4) Uani 1 1 d . . . . .
H22 H 0.563437 0.842334 0.669984 0.031 Uiso 1 1 calc R . . . .
C19 C 0.59110(7) 0.7363(3) 0.86194(10) 0.0307(5) Uani 1 1 d . . . . .
H19 H 0.598416 0.710570 0.910278 0.037 Uiso 1 1 calc R . . . .
C20 C 0.57108(7) 0.9059(3) 0.83737(11) 0.0331(5) Uani 1 1 d . . . . .
H20 H 0.564264 0.993120 0.869169 0.040 Uiso 1 1 calc R . . . .
C21 C 0.56104(7) 0.9475(3) 0.76582(12) 0.0324(5) Uani 1 1 d . . . . .
H21 H 0.548174 1.063327 0.749666 0.039 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C00B 1.230(2) . ?
O4 C16 1.217(2) . ?
O3 H3 0.8200 . ?
O3 C00H 1.415(2) . ?
O1W H1WA 0.8500 . ?
O1W H1WB 0.8498 . ?
O2 C6 1.374(2) . ?
O2 C7 1.352(2) . ?
N1 C15 1.414(2) . ?
N1 C16 1.376(2) . ?
N1 C17 1.429(2) . ?
C8 C00B 1.462(2) . ?
C8 C9 1.512(2) . ?
C8 C7 1.341(2) . ?
C1 C00B 1.468(2) . ?
C1 C6 1.386(2) . ?
C1 C2 1.403(2) . ?
C15 C10 1.388(2) . ?
C15 C14 1.379(2) . ?
C16 C9 1.540(2) . ?
C9 C10 1.520(2) . ?
C9 C00H 1.537(2) . ?
C10 C11 1.379(2) . ?
C6 C5 1.391(2) . ?
C17 C18 1.378(2) . ?
C17 C22 1.384(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.395(3) . ?
C00H H00A 0.9700 . ?
C00H H00B 0.9700 . ?
C7 H7 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.381(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.396(3) . ?
C13 H13 0.9300 . ?
C18 H18 0.9300 . ?
C18 C19 1.387(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.372(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.396(3) . ?
C3 H3A 0.9300 . ?
C22 H22 0.9300 . ?
C22 C21 1.387(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.376(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.382(3) . ?
C21 H21 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00H O3 H3 109.5 . . ?
H1WA O1W H1WB 104.5 . . ?
C7 O2 C6 118.49(14) . . ?
C15 N1 C17 123.42(13) . . ?
C16 N1 C15 110.85(14) . . ?
C16 N1 C17 123.89(14) . . ?
C00B C8 C9 117.65(14) . . ?
C7 C8 C00B 119.59(16) . . ?
C7 C8 C9 122.75(16) . . ?
C6 C1 C00B 120.42(16) . . ?
C6 C1 C2 117.66(16) . . ?
C2 C1 C00B 121.91(16) . . ?
C10 C15 N1 109.64(14) . . ?
C14 C15 N1 127.93(16) . . ?
C14 C15 C10 122.43(16) . . ?
O4 C16 N1 125.66(16) . . ?
O4 C16 C9 126.17(15) . . ?
N1 C16 C9 108.13(14) . . ?
O1 C00B C8 122.45(15) . . ?
O1 C00B C1 122.85(16) . . ?
C8 C00B C1 114.70(15) . . ?
C8 C9 C16 109.53(14) . . ?
C8 C9 C10 113.72(14) . . ?
C8 C9 C00H 115.07(14) . . ?
C10 C9 C16 101.66(13) . . ?
C10 C9 C00H 107.34(14) . . ?
C00H C9 C16 108.60(14) . . ?
C15 C10 C9 109.07(15) . . ?
C11 C10 C15 119.90(16) . . ?
C11 C10 C9 130.98(16) . . ?
O2 C6 C1 121.50(16) . . ?
O2 C6 C5 116.20(16) . . ?
C1 C6 C5 122.30(17) . . ?
C18 C17 N1 119.87(16) . . ?
C18 C17 C22 120.99(17) . . ?
C22 C17 N1 119.12(16) . . ?
C10 C11 H11 120.6 . . ?
C10 C11 C12 118.81(17) . . ?
C12 C11 H11 120.6 . . ?
O3 C00H C9 111.12(13) . . ?
O3 C00H H00A 109.4 . . ?
O3 C00H H00B 109.4 . . ?
C9 C00H H00A 109.4 . . ?
C9 C00H H00B 109.4 . . ?
H00A C00H H00B 108.0 . . ?
O2 C7 H7 117.4 . . ?
C8 C7 O2 125.26(16) . . ?
C8 C7 H7 117.4 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.36(17) . . ?
C13 C12 H12 119.8 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.88(17) . . ?
C3 C2 H2 119.6 . . ?
C15 C14 H14 121.5 . . ?
C15 C14 C13 116.98(17) . . ?
C13 C14 H14 121.5 . . ?
C12 C13 C14 121.51(17) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.31(19) . . ?
C19 C18 H18 120.3 . . ?
C6 C5 H5 120.7 . . ?
C4 C5 C6 118.61(17) . . ?
C4 C5 H5 120.7 . . ?
C5 C4 H4 119.6 . . ?
C5 C4 C3 120.80(17) . . ?
C3 C4 H4 119.6 . . ?
C2 C3 C4 119.73(18) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C17 C22 H22 120.3 . . ?
C17 C22 C21 119.38(18) . . ?
C21 C22 H22 120.3 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.04(19) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.55(18) . . ?
C21 C20 H20 119.7 . . ?
C22 C21 H21 120.1 . . ?
C20 C21 C22 119.70(19) . . ?
C20 C21 H21 120.1 . . ?

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
O4 C16 C9 C8 -53.7(2) . . . . ?
O4 C16 C9 C10 -174.28(17) . . . . ?
O4 C16 C9 C00H 72.7(2) . . . . ?
O2 C6 C5 C4 -179.00(17) . . . . ?
N1 C15 C10 C9 1.70(19) . . . . ?
N1 C15 C10 C11 179.34(15) . . . . ?
N1 C15 C14 C13 -179.92(17) . . . . ?
N1 C16 C9 C8 128.59(15) . . . . ?
N1 C16 C9 C10 7.99(17) . . . . ?
N1 C16 C9 C00H -104.99(15) . . . . ?
N1 C17 C18 C19 -177.50(16) . . . . ?
N1 C17 C22 C21 177.48(16) . . . . ?
C8 C9 C10 C15 -123.39(16) . . . . ?
C8 C9 C10 C11 59.3(2) . . . . ?
C8 C9 C00H O3 57.15(19) . . . . ?
C1 C6 C5 C4 0.7(3) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C15 N1 C16 O4 174.67(16) . . . . ?
C15 N1 C16 C9 -7.59(19) . . . . ?
C15 N1 C17 C18 115.69(19) . . . . ?
C15 N1 C17 C22 -62.6(2) . . . . ?
C15 C10 C11 C12 0.8(3) . . . . ?
C15 C14 C13 C12 0.6(3) . . . . ?
C16 N1 C15 C10 3.8(2) . . . . ?
C16 N1 C15 C14 -176.98(17) . . . . ?
C16 N1 C17 C18 -81.2(2) . . . . ?
C16 N1 C17 C22 100.6(2) . . . . ?
C16 C9 C10 C15 -5.78(18) . . . . ?
C16 C9 C10 C11 176.93(18) . . . . ?
C16 C9 C00H O3 -66.00(17) . . . . ?
C00B C8 C9 C16 -49.85(19) . . . . ?
C00B C8 C9 C10 63.1(2) . . . . ?
C00B C8 C9 C00H -172.51(14) . . . . ?
C00B C8 C7 O2 -2.3(3) . . . . ?
C00B C1 C6 O2 -0.4(3) . . . . ?
C00B C1 C6 C5 179.87(17) . . . . ?
C00B C1 C2 C3 179.27(17) . . . . ?
C9 C8 C00B O1 2.2(2) . . . . ?
C9 C8 C00B C1 -177.95(14) . . . . ?
C9 C8 C7 O2 177.31(16) . . . . ?
C9 C10 C11 C12 177.88(17) . . . . ?
C10 C15 C14 C13 -0.8(3) . . . . ?
C10 C9 C00H O3 -175.17(13) . . . . ?
C10 C11 C12 C13 -1.0(3) . . . . ?
C6 O2 C7 C8 1.4(3) . . . . ?
C6 C1 C00B O1 179.45(16) . . . . ?
C6 C1 C00B C8 -0.4(2) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C6 C5 C4 C3 -0.6(3) . . . . ?
C17 N1 C15 C10 168.89(15) . . . . ?
C17 N1 C15 C14 -11.9(3) . . . . ?
C17 N1 C16 O4 9.7(3) . . . . ?
C17 N1 C16 C9 -172.56(15) . . . . ?
C17 C18 C19 C20 0.4(3) . . . . ?
C17 C22 C21 C20 -0.3(3) . . . . ?
C11 C12 C13 C14 0.3(3) . . . . ?
C00H C9 C10 C15 108.15(16) . . . . ?
C00H C9 C10 C11 -69.1(2) . . . . ?
C7 O2 C6 C1 0.0(2) . . . . ?
C7 O2 C6 C5 179.74(16) . . . . ?
C7 C8 C00B O1 -178.16(16) . . . . ?
C7 C8 C00B C1 1.7(2) . . . . ?
C7 C8 C9 C16 130.48(17) . . . . ?
C7 C8 C9 C10 -116.56(18) . . . . ?
C7 C8 C9 C00H 7.8(2) . . . . ?
C2 C1 C00B O1 -0.7(3) . . . . ?
C2 C1 C00B C8 179.39(16) . . . . ?
C2 C1 C6 O2 179.75(16) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C14 C15 C10 C9 -177.54(16) . . . . ?
C14 C15 C10 C11 0.1(3) . . . . ?
C18 C17 C22 C21 -0.7(3) . . . . ?
C18 C19 C20 C21 -1.4(3) . . . . ?
C5 C4 C3 C2 -0.2(3) . . . . ?
C22 C17 C18 C19 0.7(3) . . . . ?
C19 C20 C21 C22 1.4(3) . . . . ?

_olex2_date_sample_data_collection 2017-11-11
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.649
_oxdiff_exptl_absorpt_empirical_full_min 0.684
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_963
_database_code_depnum_ccdc_archive 'CCDC 1843649'
loop_
_audit_author_name
_audit_author_address
'Xiong-Li Liu'
;guizhou university
China
;
_audit_update_record             
;
2018-05-16 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;
_audit_creation_date             2017-11-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H17 Cl N O4, C H4 O'
_chemical_formula_sum            'C26 H21 Cl N O5'
_chemical_formula_weight         462.89
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   9.1764(6)
_cell_length_b                   10.3922(5)
_cell_length_c                   11.8331(7)
_cell_angle_alpha                92.396(4)
_cell_angle_beta                 100.320(5)
_cell_angle_gamma                101.272(5)
_cell_volume                     1085.31(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3636
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.1600
_cell_measurement_theta_min      3.7340
_shelx_estimated_absorpt_T_max   0.805
_shelx_estimated_absorpt_T_min   0.764
_exptl_absorpt_coefficient_mu    1.895
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             482
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7160
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.418
_diffrn_reflns_theta_min         3.809
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -59.00  32.00   1.00    1.00    --  -40.98  57.00 150.00   91
  2  ω    -95.00 -26.00   1.00    1.00    --  -40.98 -37.00 -90.00   69
  3  ω     54.00  97.00   1.00    1.00    --   40.98-125.00 -30.00   43
  4  ω     43.00  70.00   1.00    1.00    --  106.95 -61.00-150.00   27
  5  ω     58.00  92.00   1.00    1.00    --  106.95 -94.00-180.00   34
  6  ω     95.00 128.00   1.00    1.00    --  106.95 -61.00-150.00   33
  7  ω    115.00 166.00   1.00    1.00    --  106.95  30.00-180.00   51
  8  ω     56.00 107.00   1.00    1.00    --  106.95 -94.00   0.00   51
  9  ω     44.00  95.00   1.00    1.00    --  106.95-125.00 -90.00   51
 10  ω     35.00 131.00   1.00    1.00    --  106.95 -45.00 -60.00   96
 11  ω     42.00 108.00   1.00    1.00    --  106.95 -94.00  90.00   66
 12  ω     40.00 128.00   1.00    1.00    --  106.95 -45.00  60.00   88
 13  ω     79.00 106.00   1.00    1.00    --  106.95  30.00 120.00   27
 14  ω    136.00 176.00   1.00    1.00    --  106.95  30.00 120.00   40
 15  ω     39.00 120.00   1.00    1.00    --  106.95-125.00 -30.00   81
 16  ω     27.00 143.00   1.00    1.00    --  106.95 -15.00 150.00  116
 17  ω    -67.00  -3.00   1.00    1.00    --  -40.98 125.00-180.00   64
 18  ω   -115.00 -17.00   1.00    1.00    --  -40.98 -37.00   0.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1506912000
_diffrn_orient_matrix_UB_12      0.0163291000
_diffrn_orient_matrix_UB_13      -0.0736852000
_diffrn_orient_matrix_UB_21      -0.0199477000
_diffrn_orient_matrix_UB_22      0.0971221000
_diffrn_orient_matrix_UB_23      0.0952390000
_diffrn_orient_matrix_UB_31      0.0854981000
_diffrn_orient_matrix_UB_32      0.1153053000
_diffrn_orient_matrix_UB_33      -0.0558864000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3658
_reflns_number_total             4207
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.923
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0599
_refine_ls_restrained_S_all      1.076
_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)+(0.1014P)²+0.5684P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1653
_refine_ls_wR_factor_ref         0.1747
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C23(H23), C5(H5), C2(H2), C24(H24), C4(H4), C16(H16), C7(H7), C13(H13),
 C22(H22), C21(H21), C19(H19), C15(H15), C20(H20), C14(H14)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C)
2.d Idealised tetrahedral OH refined as rotating group:
 O5(H5A), 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
Cl1 Cl 0.25388(7) 1.16208(6) 0.22328(6) 0.0332(2) Uani 1 1 d . . . . .
O1 O 0.56058(19) 0.77301(16) 0.22328(14) 0.0245(4) Uani 1 1 d . . . . .
O4 O 0.59343(18) 0.53524(16) 0.38338(14) 0.0236(4) Uani 1 1 d . . . . .
O2 O 0.78268(18) 1.01968(16) 0.50538(14) 0.0231(4) Uani 1 1 d . . . . .
O5 O 0.7100(2) 0.44727(17) 0.62630(15) 0.0272(4) Uani 1 1 d . . . . .
H5A H 0.620372 0.451511 0.612261 0.041 Uiso 1 1 calc GR . . . .
O3 O 0.8959(2) 0.65597(17) 0.56102(14) 0.0271(4) Uani 1 1 d . . . . .
H3 H 0.827707 0.591604 0.559974 0.041 Uiso 1 1 calc GR . . . .
N1 N 0.6932(2) 0.52277(18) 0.21887(17) 0.0206(4) Uani 1 1 d . . . . .
C1 C 0.5784(3) 0.9690(2) 0.3405(2) 0.0199(5) Uani 1 1 d . . . . .
C18 C 0.6720(3) 0.2903(2) 0.1502(2) 0.0211(5) Uani 1 1 d . . . . .
C25 C 0.6263(3) 0.8472(2) 0.30840(19) 0.0202(5) Uani 1 1 d . . . . .
C11 C 0.8056(3) 0.6010(2) 0.1696(2) 0.0215(5) Uani 1 1 d . . . . .
C23 C 0.7957(3) 0.2774(2) 0.2315(2) 0.0235(5) Uani 1 1 d . . . . .
H23 H 0.833711 0.341156 0.292760 0.028 Uiso 1 1 calc R . . . .
C12 C 0.6840(2) 0.5787(2) 0.3232(2) 0.0199(5) Uani 1 1 d . . . . .
C6 C 0.6590(3) 1.0502(2) 0.4365(2) 0.0207(5) Uani 1 1 d . . . . .
C5 C 0.6185(3) 1.1682(2) 0.4676(2) 0.0243(5) Uani 1 1 d . . . . .
H5 H 0.674591 1.222547 0.531308 0.029 Uiso 1 1 calc R . . . .
C9 C 0.8153(3) 0.6996(2) 0.35595(19) 0.0199(5) Uani 1 1 d . . . . .
C8 C 0.7578(3) 0.8212(2) 0.3866(2) 0.0195(5) Uani 1 1 d . . . . .
C2 C 0.4515(3) 1.0035(2) 0.2749(2) 0.0225(5) Uani 1 1 d . . . . .
H2 H 0.394864 0.949450 0.211131 0.027 Uiso 1 1 calc R . . . .
C24 C 0.9356(3) 0.6628(2) 0.4522(2) 0.0237(5) Uani 1 1 d . . . . .
H24 H 1.027270 0.646540 0.438559 0.028 Uiso 1 1 calc R . . . .
C4 C 0.4939(3) 1.2018(2) 0.4017(2) 0.0257(5) Uani 1 1 d . . . . .
H4 H 0.464627 1.279431 0.420813 0.031 Uiso 1 1 calc R . . . .
C16 C 0.9932(3) 0.8015(2) 0.2181(2) 0.0230(5) Uani 1 1 d . . . . .
H16 H 1.043902 0.873126 0.269459 0.028 Uiso 1 1 calc R . . . .
C10 C 0.8792(3) 0.7094(2) 0.2468(2) 0.0201(5) Uani 1 1 d . . . . .
C7 C 0.8241(3) 0.9051(2) 0.4785(2) 0.0211(5) Uani 1 1 d . . . . .
H7 H 0.904942 0.883358 0.527972 0.025 Uiso 1 1 calc R . . . .
C13 C 0.8425(3) 0.5824(2) 0.0631(2) 0.0258(5) Uani 1 1 d . . . . .
H13 H 0.793108 0.509694 0.012606 0.031 Uiso 1 1 calc R . . . .
C22 C 0.8639(3) 0.1697(2) 0.2225(2) 0.0258(5) Uani 1 1 d . . . . .
H22 H 0.947623 0.162434 0.277319 0.031 Uiso 1 1 calc R . . . .
C17 C 0.5923(3) 0.4038(2) 0.1614(2) 0.0234(5) Uani 1 1 d . . . . .
H17A H 0.546148 0.422407 0.085102 0.028 Uiso 1 1 calc R . . . .
H17B H 0.512024 0.377761 0.204224 0.028 Uiso 1 1 calc R . . . .
C21 C 0.8074(3) 0.0736(2) 0.1324(2) 0.0265(5) Uani 1 1 d . . . . .
H21 H 0.852303 0.001376 0.126685 0.032 Uiso 1 1 calc R . . . .
C19 C 0.6170(3) 0.1951(2) 0.0582(2) 0.0238(5) Uani 1 1 d . . . . .
H19 H 0.535837 0.204279 0.001774 0.029 Uiso 1 1 calc R . . . .
C15 C 1.0312(3) 0.7852(2) 0.1099(2) 0.0274(5) Uani 1 1 d . . . . .
H15 H 1.106892 0.847247 0.088434 0.033 Uiso 1 1 calc R . . . .
C3 C 0.4118(3) 1.1189(2) 0.3062(2) 0.0248(5) Uani 1 1 d . . . . .
C20 C 0.6830(3) 0.0860(2) 0.0505(2) 0.0259(5) Uani 1 1 d . . . . .
H20 H 0.643617 0.021163 -0.009795 0.031 Uiso 1 1 calc R . . . .
C14 C 0.9569(3) 0.6773(3) 0.0343(2) 0.0280(5) Uani 1 1 d . . . . .
H14 H 0.984067 0.667980 -0.037238 0.034 Uiso 1 1 calc R . . . .
C26 C 0.7616(3) 0.4564(3) 0.7478(2) 0.0292(5) Uani 1 1 d . . . . .
H26A H 0.864172 0.444258 0.764215 0.044 Uiso 1 1 calc GR . . . .
H26B H 0.698356 0.389497 0.780985 0.044 Uiso 1 1 calc GR . . . .
H26C H 0.757217 0.541512 0.780038 0.044 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
Cl1 C3 1.745(3) . ?
O1 C25 1.228(3) . ?
O4 C12 1.222(3) . ?
O2 C6 1.373(3) . ?
O2 C7 1.361(3) . ?
O5 H5A 0.8200 . ?
O5 C26 1.424(3) . ?
O3 H3 0.8200 . ?
O3 C24 1.400(3) . ?
N1 C11 1.411(3) . ?
N1 C12 1.366(3) . ?
N1 C17 1.451(3) . ?
C1 C25 1.476(3) . ?
C1 C6 1.386(3) . ?
C1 C2 1.397(3) . ?
C18 C23 1.382(3) . ?
C18 C17 1.517(3) . ?
C18 C19 1.392(3) . ?
C25 C8 1.460(3) . ?
C11 C10 1.398(3) . ?
C11 C13 1.378(3) . ?
C23 H23 0.9300 . ?
C23 C22 1.394(3) . ?
C12 C9 1.543(3) . ?
C6 C5 1.402(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.377(4) . ?
C9 C8 1.516(3) . ?
C9 C24 1.553(3) . ?
C9 C10 1.511(3) . ?
C8 C7 1.337(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.374(3) . ?
C24 H24 0.9300 . ?
C4 H4 0.9300 . ?
C4 C3 1.396(4) . ?
C16 H16 0.9300 . ?
C16 C10 1.375(3) . ?
C16 C15 1.398(3) . ?
C7 H7 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.394(4) . ?
C22 H22 0.9300 . ?
C22 C21 1.383(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C21 H21 0.9300 . ?
C21 C20 1.390(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.393(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.386(4) . ?
C20 H20 0.9300 . ?
C14 H14 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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 O2 C6 118.20(18) . . ?
C26 O5 H5A 109.5 . . ?
C24 O3 H3 109.5 . . ?
C11 N1 C17 124.00(19) . . ?
C12 N1 C11 111.40(19) . . ?
C12 N1 C17 124.42(19) . . ?
C6 C1 C25 120.2(2) . . ?
C6 C1 C2 119.4(2) . . ?
C2 C1 C25 120.4(2) . . ?
C23 C18 C17 121.3(2) . . ?
C23 C18 C19 119.2(2) . . ?
C19 C18 C17 119.5(2) . . ?
O1 C25 C1 122.9(2) . . ?
O1 C25 C8 122.6(2) . . ?
C8 C25 C1 114.6(2) . . ?
C10 C11 N1 109.0(2) . . ?
C13 C11 N1 128.8(2) . . ?
C13 C11 C10 122.2(2) . . ?
C18 C23 H23 119.7 . . ?
C18 C23 C22 120.6(2) . . ?
C22 C23 H23 119.7 . . ?
O4 C12 N1 125.7(2) . . ?
O4 C12 C9 126.0(2) . . ?
N1 C12 C9 108.11(18) . . ?
O2 C6 C1 121.8(2) . . ?
O2 C6 C5 116.6(2) . . ?
C1 C6 C5 121.6(2) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 C6 118.6(2) . . ?
C4 C5 H5 120.7 . . ?
C12 C9 C24 107.84(18) . . ?
C8 C9 C12 111.16(18) . . ?
C8 C9 C24 114.66(19) . . ?
C10 C9 C12 101.63(17) . . ?
C10 C9 C8 112.52(18) . . ?
C10 C9 C24 108.14(18) . . ?
C25 C8 C9 117.0(2) . . ?
C7 C8 C25 119.9(2) . . ?
C7 C8 C9 123.1(2) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.8(2) . . ?
C3 C2 H2 120.6 . . ?
O3 C24 C9 115.14(19) . . ?
O3 C24 H24 122.4 . . ?
C9 C24 H24 122.4 . . ?
C5 C4 H4 120.2 . . ?
C5 C4 C3 119.7(2) . . ?
C3 C4 H4 120.2 . . ?
C10 C16 H16 120.8 . . ?
C10 C16 C15 118.5(2) . . ?
C15 C16 H16 120.8 . . ?
C11 C10 C9 109.19(19) . . ?
C16 C10 C11 120.2(2) . . ?
C16 C10 C9 130.5(2) . . ?
O2 C7 H7 117.4 . . ?
C8 C7 O2 125.2(2) . . ?
C8 C7 H7 117.4 . . ?
C11 C13 H13 121.4 . . ?
C11 C13 C14 117.2(2) . . ?
C14 C13 H13 121.4 . . ?
C23 C22 H22 119.9 . . ?
C21 C22 C23 120.2(2) . . ?
C21 C22 H22 119.9 . . ?
N1 C17 C18 113.01(19) . . ?
N1 C17 H17A 109.0 . . ?
N1 C17 H17B 109.0 . . ?
C18 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C22 C21 H21 120.3 . . ?
C22 C21 C20 119.4(2) . . ?
C20 C21 H21 120.3 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.2(2) . . ?
C20 C19 H19 119.9 . . ?
C16 C15 H15 119.7 . . ?
C14 C15 C16 120.6(2) . . ?
C14 C15 H15 119.7 . . ?
C2 C3 Cl1 118.6(2) . . ?
C2 C3 C4 122.0(2) . . ?
C4 C3 Cl1 119.40(19) . . ?
C21 C20 C19 120.2(2) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.4(2) . . ?
C15 C14 H14 119.3 . . ?
O5 C26 H26A 109.5 . . ?
O5 C26 H26B 109.5 . . ?
O5 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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 C25 C8 C9 2.3(3) . . . . ?
O1 C25 C8 C7 -179.5(2) . . . . ?
O4 C12 C9 C8 -56.7(3) . . . . ?
O4 C12 C9 C24 69.8(3) . . . . ?
O4 C12 C9 C10 -176.6(2) . . . . ?
O2 C6 C5 C4 -179.14(19) . . . . ?
N1 C11 C10 C9 2.2(3) . . . . ?
N1 C11 C10 C16 -179.4(2) . . . . ?
N1 C11 C13 C14 178.4(2) . . . . ?
N1 C12 C9 C8 127.7(2) . . . . ?
N1 C12 C9 C24 -105.8(2) . . . . ?
N1 C12 C9 C10 7.8(2) . . . . ?
C1 C25 C8 C9 -178.16(18) . . . . ?
C1 C25 C8 C7 0.1(3) . . . . ?
C1 C6 C5 C4 1.2(3) . . . . ?
C1 C2 C3 Cl1 179.53(17) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C18 C23 C22 C21 -0.6(4) . . . . ?
C18 C19 C20 C21 -2.1(4) . . . . ?
C25 C1 C6 O2 -1.2(3) . . . . ?
C25 C1 C6 C5 178.4(2) . . . . ?
C25 C1 C2 C3 -178.9(2) . . . . ?
C25 C8 C7 O2 -2.6(4) . . . . ?
C11 N1 C12 O4 177.3(2) . . . . ?
C11 N1 C12 C9 -7.1(2) . . . . ?
C11 N1 C17 C18 70.7(3) . . . . ?
C11 C13 C14 C15 0.4(4) . . . . ?
C23 C18 C17 N1 31.0(3) . . . . ?
C23 C18 C19 C20 2.0(3) . . . . ?
C23 C22 C21 C20 0.5(4) . . . . ?
C12 N1 C11 C10 3.2(3) . . . . ?
C12 N1 C11 C13 -175.6(2) . . . . ?
C12 N1 C17 C18 -114.6(2) . . . . ?
C12 C9 C8 C25 -46.8(3) . . . . ?
C12 C9 C8 C7 135.0(2) . . . . ?
C12 C9 C24 O3 -73.7(2) . . . . ?
C12 C9 C10 C11 -6.0(2) . . . . ?
C12 C9 C10 C16 175.9(2) . . . . ?
C6 O2 C7 C8 3.1(3) . . . . ?
C6 C1 C25 O1 -178.8(2) . . . . ?
C6 C1 C25 C8 1.7(3) . . . . ?
C6 C1 C2 C3 1.3(3) . . . . ?
C6 C5 C4 C3 -0.2(3) . . . . ?
C5 C4 C3 Cl1 179.95(18) . . . . ?
C5 C4 C3 C2 -0.2(4) . . . . ?
C9 C8 C7 O2 175.6(2) . . . . ?
C8 C9 C24 O3 50.7(3) . . . . ?
C8 C9 C10 C11 -124.9(2) . . . . ?
C8 C9 C10 C16 56.9(3) . . . . ?
C2 C1 C25 O1 1.4(3) . . . . ?
C2 C1 C25 C8 -178.14(19) . . . . ?
C2 C1 C6 O2 178.62(19) . . . . ?
C2 C1 C6 C5 -1.7(3) . . . . ?
C24 C9 C8 C25 -169.47(18) . . . . ?
C24 C9 C8 C7 12.4(3) . . . . ?
C24 C9 C10 C11 107.4(2) . . . . ?
C24 C9 C10 C16 -70.8(3) . . . . ?
C16 C15 C14 C13 0.2(4) . . . . ?
C10 C11 C13 C14 -0.3(4) . . . . ?
C10 C9 C8 C25 66.4(3) . . . . ?
C10 C9 C8 C7 -111.8(2) . . . . ?
C10 C9 C24 O3 177.14(18) . . . . ?
C10 C16 C15 C14 -1.0(4) . . . . ?
C7 O2 C6 C1 -1.1(3) . . . . ?
C7 O2 C6 C5 179.23(19) . . . . ?
C13 C11 C10 C9 -178.8(2) . . . . ?
C13 C11 C10 C16 -0.5(4) . . . . ?
C22 C21 C20 C19 0.8(4) . . . . ?
C17 N1 C11 C10 178.5(2) . . . . ?
C17 N1 C11 C13 -0.4(4) . . . . ?
C17 N1 C12 O4 2.1(4) . . . . ?
C17 N1 C12 C9 177.64(19) . . . . ?
C17 C18 C23 C22 177.3(2) . . . . ?
C17 C18 C19 C20 -176.0(2) . . . . ?
C19 C18 C23 C22 -0.6(3) . . . . ?
C19 C18 C17 N1 -151.1(2) . . . . ?
C15 C16 C10 C11 1.1(3) . . . . ?
C15 C16 C10 C9 179.1(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.927
_oxdiff_exptl_absorpt_empirical_full_min 0.677
####################################################################### 
# 
# 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_mo_gd_lxl31_0m
_database_code_depnum_ccdc_archive 'CCDC 1953704'
loop_
_audit_author_name
_audit_author_address
'Xiong-Li Liu'
;guizhou university
China
;
_audit_update_record             
;
2019-09-15 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H14 Cl N O3'
_chemical_formula_sum            'C19 H14 Cl N O3'
_chemical_formula_weight         339.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.8644(7)
_cell_length_b                   11.2698(9)
_cell_length_c                   15.5335(13)
_cell_angle_alpha                90
_cell_angle_beta                 98.7490(10)
_cell_angle_gamma                90
_cell_volume                     1533.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9394
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      30.92

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   0.2949
_exptl_transmission_factor_max   0.3374
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.470
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.267
_shelx_estimated_absorpt_T_min   0.878
_shelx_estimated_absorpt_T_max   0.924
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16779
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.242
_diffrn_reflns_theta_max         31.016
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4548
_reflns_number_gt                4041
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0499P)²+0.6911P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4548
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0946
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.34032(3) 0.12748(2) 0.76189(2) 0.01960(8) Uani 1 1 d . . . . .
O1 O 0.86709(9) 0.45782(7) 0.60769(5) 0.01676(16) Uani 1 1 d . . . . .
O2 O 0.75686(10) 0.70232(7) 0.87291(6) 0.02040(17) Uani 1 1 d . . . . .
O3 O 0.54073(9) 0.65528(7) 0.70143(5) 0.01848(16) Uani 1 1 d . . . . .
N1 N 0.54178(11) 0.59812(8) 0.89489(6) 0.01496(17) Uani 1 1 d . . . . .
C1 C 0.68651(13) 0.58282(10) 0.40341(7) 0.0178(2) Uani 1 1 d . . . . .
H1 H 0.6958 0.5787 0.3434 0.021 Uiso 1 1 calc R U . . .
C2 C 0.78479(12) 0.51823(10) 0.46330(7) 0.0167(2) Uani 1 1 d . . . . .
H14 H 0.8620 0.4700 0.4451 0.020 Uiso 1 1 calc R U . . .
C3 C 0.76819(12) 0.52532(9) 0.55112(7) 0.01410(19) Uani 1 1 d . . . . .
C4 C 0.84638(12) 0.45218(10) 0.69195(7) 0.0158(2) Uani 1 1 d . . . . .
H13 H 0.9115 0.4009 0.7293 0.019 Uiso 1 1 calc R U . . .
C5 C 0.74024(12) 0.51384(9) 0.72719(7) 0.01348(19) Uani 1 1 d . . . . .
C6 C 0.71820(12) 0.49577(9) 0.82133(7) 0.01344(19) Uani 1 1 d . . . . .
C7 C 0.57695(12) 0.42217(9) 0.82669(7) 0.01309(18) Uani 1 1 d . . . . .
C8 C 0.53907(12) 0.31007(9) 0.79485(7) 0.01401(19) Uani 1 1 d . . . . .
H6 H 0.6070 0.2652 0.7659 0.017 Uiso 1 1 calc R U . . .
C9 C 0.39677(12) 0.26516(9) 0.80686(7) 0.01515(19) Uani 1 1 d . . . . .
C10 C 0.29598(12) 0.32849(10) 0.84996(7) 0.0172(2) Uani 1 1 d . . . . .
H2 H 0.2003 0.2950 0.8571 0.021 Uiso 1 1 calc R U . . .
C11 C 0.47684(12) 0.48737(9) 0.86999(7) 0.01399(19) Uani 1 1 d . . . . .
C12 C 0.46239(13) 0.69388(10) 0.93186(7) 0.0187(2) Uani 1 1 d . . . . .
H3 H 0.5311 0.7620 0.9440 0.028 Uiso 1 1 calc R U . . .
H5 H 0.4298 0.6669 0.9861 0.028 Uiso 1 1 calc R U . . .
H4 H 0.3727 0.7173 0.8904 0.028 Uiso 1 1 calc R U . . .
C13 C 0.67749(12) 0.61382(9) 0.86360(7) 0.01516(19) Uani 1 1 d . . . . .
C14 C 0.33627(12) 0.44193(10) 0.88275(7) 0.0166(2) Uani 1 1 d . . . . .
H7 H 0.2695 0.4863 0.9128 0.020 Uiso 1 1 calc R U . . .
C15 C 0.86003(13) 0.44499(10) 0.87938(7) 0.0183(2) Uani 1 1 d . . . . .
H10 H 0.8393 0.4376 0.9393 0.027 Uiso 1 1 calc R U . . .
H9 H 0.9469 0.4984 0.8781 0.027 Uiso 1 1 calc R U . . .
H8 H 0.8841 0.3667 0.8576 0.027 Uiso 1 1 calc R U . . .
C16 C 0.63697(12) 0.59384(9) 0.67229(7) 0.01361(19) Uani 1 1 d . . . . .
C17 C 0.65516(12) 0.59459(9) 0.57984(7) 0.01354(19) Uani 1 1 d . . . . .
C18 C 0.55676(12) 0.65955(10) 0.51735(7) 0.0157(2) Uani 1 1 d . . . . .
H12 H 0.4787 0.7072 0.5352 0.019 Uiso 1 1 calc R U . . .
C19 C 0.57270(13) 0.65466(10) 0.43054(7) 0.0169(2) Uani 1 1 d . . . . .
H11 H 0.5068 0.6998 0.3890 0.020 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C9 1.7435(11) . ?
O1 C4 1.3505(13) . ?
O1 C3 1.3730(13) . ?
O2 C13 1.2165(13) . ?
O3 C16 1.2367(13) . ?
N1 C13 1.3757(14) . ?
N1 C11 1.4040(14) . ?
N1 C12 1.4535(14) . ?
C1 C2 1.3811(16) . ?
C1 C19 1.4073(16) . ?
C1 H1 0.9500 . ?
C2 C3 1.3965(15) . ?
C2 H14 0.9500 . ?
C3 C17 1.3957(14) . ?
C4 C5 1.3507(14) . ?
C4 H13 0.9500 . ?
C5 C16 1.4630(14) . ?
C5 C6 1.5182(14) . ?
C6 C7 1.5147(14) . ?
C6 C15 1.5416(15) . ?
C6 C13 1.5504(14) . ?
C7 C8 1.3795(14) . ?
C7 C11 1.4005(14) . ?
C8 C9 1.3977(14) . ?
C8 H6 0.9500 . ?
C9 C10 1.3921(15) . ?
C10 C14 1.4021(16) . ?
C10 H2 0.9500 . ?
C11 C14 1.3890(15) . ?
C12 H3 0.9800 . ?
C12 H5 0.9800 . ?
C12 H4 0.9800 . ?
C14 H7 0.9500 . ?
C15 H10 0.9800 . ?
C15 H9 0.9800 . ?
C15 H8 0.9800 . ?
C16 C17 1.4694(14) . ?
C17 C18 1.4077(14) . ?
C18 C19 1.3781(15) . ?
C18 H12 0.9500 . ?
C19 H11 0.9500 . ?

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
C4 O1 C3 118.60(8) . . ?
C13 N1 C11 111.16(9) . . ?
C13 N1 C12 123.09(9) . . ?
C11 N1 C12 124.48(9) . . ?
C2 C1 C19 120.60(10) . . ?
C2 C1 H1 119.7 . . ?
C19 C1 H1 119.7 . . ?
C1 C2 C3 118.58(10) . . ?
C1 C2 H14 120.7 . . ?
C3 C2 H14 120.7 . . ?
O1 C3 C17 121.66(9) . . ?
O1 C3 C2 116.21(9) . . ?
C17 C3 C2 122.11(10) . . ?
C5 C4 O1 125.05(10) . . ?
C5 C4 H13 117.5 . . ?
O1 C4 H13 117.5 . . ?
C4 C5 C16 119.57(10) . . ?
C4 C5 C6 121.39(9) . . ?
C16 C5 C6 118.90(9) . . ?
C7 C6 C5 110.79(8) . . ?
C7 C6 C15 111.84(9) . . ?
C5 C6 C15 113.59(9) . . ?
C7 C6 C13 101.48(8) . . ?
C5 C6 C13 111.42(8) . . ?
C15 C6 C13 107.01(9) . . ?
C8 C7 C11 121.01(10) . . ?
C8 C7 C6 129.79(9) . . ?
C11 C7 C6 109.19(9) . . ?
C7 C8 C9 117.34(10) . . ?
C7 C8 H6 121.3 . . ?
C9 C8 H6 121.3 . . ?
C10 C9 C8 122.46(10) . . ?
C10 C9 Cl1 118.88(8) . . ?
C8 C9 Cl1 118.60(8) . . ?
C9 C10 C14 119.70(10) . . ?
C9 C10 H2 120.1 . . ?
C14 C10 H2 120.1 . . ?
C14 C11 C7 121.52(10) . . ?
C14 C11 N1 128.87(10) . . ?
C7 C11 N1 109.61(9) . . ?
N1 C12 H3 109.5 . . ?
N1 C12 H5 109.5 . . ?
H3 C12 H5 109.5 . . ?
N1 C12 H4 109.5 . . ?
H3 C12 H4 109.5 . . ?
H5 C12 H4 109.5 . . ?
O2 C13 N1 125.77(10) . . ?
O2 C13 C6 125.89(10) . . ?
N1 C13 C6 108.16(9) . . ?
C11 C14 C10 117.96(10) . . ?
C11 C14 H7 121.0 . . ?
C10 C14 H7 121.0 . . ?
C6 C15 H10 109.5 . . ?
C6 C15 H9 109.5 . . ?
H10 C15 H9 109.5 . . ?
C6 C15 H8 109.5 . . ?
H10 C15 H8 109.5 . . ?
H9 C15 H8 109.5 . . ?
O3 C16 C5 122.48(10) . . ?
O3 C16 C17 122.61(10) . . ?
C5 C16 C17 114.91(9) . . ?
C3 C17 C18 118.05(10) . . ?
C3 C17 C16 120.00(9) . . ?
C18 C17 C16 121.89(9) . . ?
C19 C18 C17 120.59(10) . . ?
C19 C18 H12 119.7 . . ?
C17 C18 H12 119.7 . . ?
C18 C19 C1 120.06(10) . . ?
C18 C19 H11 120.0 . . ?
C1 C19 H11 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C19 C1 C2 C3 0.33(16) . . . . ?
C4 O1 C3 C17 4.91(15) . . . . ?
C4 O1 C3 C2 -173.52(9) . . . . ?
C1 C2 C3 O1 178.93(10) . . . . ?
C1 C2 C3 C17 0.51(16) . . . . ?
C3 O1 C4 C5 -4.17(16) . . . . ?
O1 C4 C5 C16 0.14(17) . . . . ?
O1 C4 C5 C6 175.88(10) . . . . ?
C4 C5 C6 C7 -103.64(11) . . . . ?
C16 C5 C6 C7 72.12(11) . . . . ?
C4 C5 C6 C15 23.23(14) . . . . ?
C16 C5 C6 C15 -161.00(9) . . . . ?
C4 C5 C6 C13 144.17(10) . . . . ?
C16 C5 C6 C13 -40.06(12) . . . . ?
C5 C6 C7 C8 57.15(14) . . . . ?
C15 C6 C7 C8 -70.69(14) . . . . ?
C13 C6 C7 C8 175.56(10) . . . . ?
C5 C6 C7 C11 -121.34(9) . . . . ?
C15 C6 C7 C11 110.82(10) . . . . ?
C13 C6 C7 C11 -2.94(11) . . . . ?
C11 C7 C8 C9 0.60(15) . . . . ?
C6 C7 C8 C9 -177.74(10) . . . . ?
C7 C8 C9 C10 -0.81(16) . . . . ?
C7 C8 C9 Cl1 176.27(8) . . . . ?
C8 C9 C10 C14 0.25(16) . . . . ?
Cl1 C9 C10 C14 -176.82(8) . . . . ?
C8 C7 C11 C14 0.16(16) . . . . ?
C6 C7 C11 C14 178.81(9) . . . . ?
C8 C7 C11 N1 -179.47(9) . . . . ?
C6 C7 C11 N1 -0.82(12) . . . . ?
C13 N1 C11 C14 -174.70(11) . . . . ?
C12 N1 C11 C14 -7.28(17) . . . . ?
C13 N1 C11 C7 4.90(12) . . . . ?
C12 N1 C11 C7 172.32(10) . . . . ?
C11 N1 C13 O2 177.90(11) . . . . ?
C12 N1 C13 O2 10.27(17) . . . . ?
C11 N1 C13 C6 -6.76(12) . . . . ?
C12 N1 C13 C6 -174.38(9) . . . . ?
C7 C6 C13 O2 -178.88(11) . . . . ?
C5 C6 C13 O2 -60.93(14) . . . . ?
C15 C6 C13 O2 63.80(14) . . . . ?
C7 C6 C13 N1 5.78(11) . . . . ?
C5 C6 C13 N1 123.74(9) . . . . ?
C15 C6 C13 N1 -111.54(10) . . . . ?
C7 C11 C14 C10 -0.73(16) . . . . ?
N1 C11 C14 C10 178.83(10) . . . . ?
C9 C10 C14 C11 0.52(16) . . . . ?
C4 C5 C16 O3 -177.73(10) . . . . ?
C6 C5 C16 O3 6.43(15) . . . . ?
C4 C5 C16 C17 2.93(14) . . . . ?
C6 C5 C16 C17 -172.92(9) . . . . ?
O1 C3 C17 C18 -178.91(9) . . . . ?
C2 C3 C17 C18 -0.58(15) . . . . ?
O1 C3 C17 C16 -1.76(15) . . . . ?
C2 C3 C17 C16 176.57(10) . . . . ?
O3 C16 C17 C3 178.54(10) . . . . ?
C5 C16 C17 C3 -2.12(14) . . . . ?
O3 C16 C17 C18 -4.42(16) . . . . ?
C5 C16 C17 C18 174.92(9) . . . . ?
C3 C17 C18 C19 -0.20(15) . . . . ?
C16 C17 C18 C19 -177.29(10) . . . . ?
C17 C18 C19 C1 1.02(16) . . . . ?
C2 C1 C19 C18 -1.10(17) . . . . ?

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
C12 H4 Cl1 0.98 2.97 3.7896(12) 141.7 2_556
C12 H3 O1 0.98 2.56 3.4341(14) 148.6 2_656
C12 H4 Cl1 0.98 2.97 3.7896(12) 141.7 2_556
C12 H3 O1 0.98 2.56 3.4341(14) 148.6 2_656
C12 H3 O1 0.98 2.56 3.4341(14) 148.6 2_656
C12 H4 Cl1 0.98 2.97 3.7896(12) 141.7 2_556
C12 H3 O1 0.98 2.56 3.4341(14) 148.6 2_656
C12 H4 Cl1 0.98 2.97 3.7896(12) 141.7 2_556

_refine_diff_density_max         0.492
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_my22
_database_code_depnum_ccdc_archive 'CCDC 1843652'
loop_
_audit_author_name
_audit_author_address
'Xiong-Li Liu'
;guizhou university
China
;
_audit_update_record             
;
2018-05-16 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;
_audit_creation_date             2017-11-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H14 F N O4'
_chemical_formula_sum            'C19 H14 F N O4'
_chemical_formula_weight         339.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.3770(3)
_cell_length_b                   23.8555(13)
_cell_length_c                   9.8072(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.362(5)
_cell_angle_gamma                90
_cell_volume                     1485.41(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3791
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      28.7260
_cell_measurement_theta_min      3.2890
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88375
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10770
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.458
_diffrn_reflns_theta_min         2.254
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -35.00  57.00   1.00    2.06    --  -11.59  57.00-180.00   92
  2  ω    -83.00  16.00   1.00    2.06    --  -11.59 -57.00  30.00   99
  3  ω    -13.00  64.00   1.00    2.06    --   11.74  77.00 -60.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0412517000
_diffrn_orient_matrix_UB_12      -0.0205882000
_diffrn_orient_matrix_UB_13      -0.0423426000
_diffrn_orient_matrix_UB_21      0.0950458000
_diffrn_orient_matrix_UB_22      -0.0005058000
_diffrn_orient_matrix_UB_23      0.0437398000
_diffrn_orient_matrix_UB_31      -0.0417919000
_diffrn_orient_matrix_UB_32      -0.0214557000
_diffrn_orient_matrix_UB_33      0.0395918000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3038
_reflns_number_total             3639
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0070(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3639
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.047
_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)+(0.0450P)²+0.6769P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1026
_refine_ls_wR_factor_ref         0.1098
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C2(H2), C11(H11), C7(H7), C14(H14), C12(H12), C4(H4A), C13(H13)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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 0.93100(14) 0.58085(4) 0.79737(9) 0.0240(2) Uani 1 1 d . . . . .
O2 O 0.15837(16) 0.54335(4) 0.52565(11) 0.0189(2) Uani 1 1 d . . . . .
O4 O -0.03030(17) 0.54341(4) 0.10568(12) 0.0213(3) Uani 1 1 d . . . . .
H4 H 0.071646 0.536702 0.063196 0.032 Uiso 1 1 calc GR . . . .
O3 O 0.40343(17) 0.58063(4) 0.05763(11) 0.0213(3) Uani 1 1 d . . . . .
O1 O 0.56686(16) 0.64337(5) 0.34042(11) 0.0206(3) Uani 1 1 d . . . . .
N1 N 0.37295(19) 0.67700(5) 0.05523(13) 0.0165(3) Uani 1 1 d . . . . .
C1 C 0.4989(2) 0.58733(6) 0.53067(15) 0.0145(3) Uani 1 1 d . . . . .
C8 C 0.2307(2) 0.60086(6) 0.33505(15) 0.0146(3) Uani 1 1 d . . . . .
C18 C 0.4430(2) 0.61317(6) 0.39620(15) 0.0149(3) Uani 1 1 d . . . . .
C16 C 0.3294(2) 0.62393(6) 0.09789(15) 0.0162(3) Uani 1 1 d . . . . .
C6 C 0.3540(2) 0.55413(6) 0.59135(15) 0.0153(3) Uani 1 1 d . . . . .
C3 C 0.7396(2) 0.57238(6) 0.72788(16) 0.0177(3) Uani 1 1 d . . . . .
C5 C 0.3987(2) 0.53073(6) 0.72099(16) 0.0183(3) Uani 1 1 d . . . . .
H5 H 0.298571 0.509273 0.760335 0.022 Uiso 1 1 calc R . . . .
C2 C 0.6972(2) 0.59669(6) 0.60222(15) 0.0167(3) Uani 1 1 d . . . . .
H2 H 0.797115 0.618915 0.564908 0.020 Uiso 1 1 calc R . . . .
C11 C 0.0015(2) 0.72281(6) 0.28508(16) 0.0187(3) Uani 1 1 d . . . . .
H11 H -0.088800 0.705732 0.341620 0.022 Uiso 1 1 calc R . . . .
C15 C 0.2631(2) 0.71733(6) 0.12413(15) 0.0159(3) Uani 1 1 d . . . . .
C7 C 0.1066(2) 0.56700(6) 0.40151(15) 0.0170(3) Uani 1 1 d . . . . .
H7 H -0.026445 0.559105 0.358668 0.020 Uiso 1 1 calc R . . . .
C10 C 0.1309(2) 0.69108(6) 0.21026(15) 0.0156(3) Uani 1 1 d . . . . .
C14 C 0.2750(2) 0.77502(6) 0.11297(16) 0.0193(3) Uani 1 1 d . . . . .
H14 H 0.365729 0.791955 0.056475 0.023 Uiso 1 1 calc R . . . .
C9 C 0.1574(2) 0.62807(6) 0.19913(15) 0.0150(3) Uani 1 1 d . . . . .
C19 C -0.0452(2) 0.60208(6) 0.12671(16) 0.0179(3) Uani 1 1 d . . . . .
H19A H -0.161494 0.609432 0.181251 0.021 Uiso 1 1 calc R . . . .
H19B H -0.076638 0.620292 0.038746 0.021 Uiso 1 1 calc R . . . .
C12 C 0.0093(2) 0.78139(6) 0.27393(17) 0.0211(3) Uani 1 1 d . . . . .
H12 H -0.077239 0.803465 0.323148 0.025 Uiso 1 1 calc R . . . .
C4 C 0.5942(2) 0.53999(6) 0.78986(16) 0.0179(3) Uani 1 1 d . . . . .
H4A H 0.628168 0.524795 0.876432 0.022 Uiso 1 1 calc R . . . .
C13 C 0.1454(2) 0.80665(6) 0.18994(17) 0.0211(3) Uani 1 1 d . . . . .
H13 H 0.150049 0.845559 0.184975 0.025 Uiso 1 1 calc R . . . .
C17 C 0.5330(2) 0.69038(7) -0.03497(16) 0.0212(3) Uani 1 1 d . . . . .
H17A H 0.654840 0.705212 0.017789 0.032 Uiso 1 1 calc GR . . . .
H17B H 0.479082 0.717751 -0.100938 0.032 Uiso 1 1 calc GR . . . .
H17C H 0.571200 0.657043 -0.081588 0.032 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 C3 1.3562(17) . ?
O2 C6 1.3739(17) . ?
O2 C7 1.3546(18) . ?
O4 H4 0.8200 . ?
O4 C19 1.4192(18) . ?
O3 C16 1.2166(17) . ?
O1 C18 1.2340(17) . ?
N1 C16 1.3700(18) . ?
N1 C15 1.4005(18) . ?
N1 C17 1.4473(18) . ?
C1 C18 1.469(2) . ?
C1 C6 1.392(2) . ?
C1 C2 1.405(2) . ?
C8 C18 1.458(2) . ?
C8 C7 1.342(2) . ?
C8 C9 1.517(2) . ?
C16 C9 1.550(2) . ?
C6 C5 1.393(2) . ?
C3 C2 1.366(2) . ?
C3 C4 1.390(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.379(2) . ?
C2 H2 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.380(2) . ?
C11 C12 1.403(2) . ?
C15 C10 1.396(2) . ?
C15 C14 1.383(2) . ?
C7 H7 0.9300 . ?
C10 C9 1.5179(19) . ?
C14 H14 0.9300 . ?
C14 C13 1.393(2) . ?
C9 C19 1.545(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C12 H12 0.9300 . ?
C12 C13 1.388(2) . ?
C4 H4A 0.9300 . ?
C13 H13 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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 O2 C6 118.55(11) . . ?
C19 O4 H4 109.5 . . ?
C16 N1 C15 111.26(12) . . ?
C16 N1 C17 124.40(12) . . ?
C15 N1 C17 123.82(12) . . ?
C6 C1 C18 120.47(13) . . ?
C6 C1 C2 118.63(13) . . ?
C2 C1 C18 120.88(13) . . ?
C18 C8 C9 118.24(12) . . ?
C7 C8 C18 119.26(13) . . ?
C7 C8 C9 122.49(13) . . ?
O1 C18 C1 122.08(13) . . ?
O1 C18 C8 122.91(13) . . ?
C8 C18 C1 115.01(12) . . ?
O3 C16 N1 126.13(14) . . ?
O3 C16 C9 125.54(13) . . ?
N1 C16 C9 108.21(12) . . ?
O2 C6 C1 121.07(13) . . ?
O2 C6 C5 116.89(13) . . ?
C1 C6 C5 122.04(13) . . ?
F1 C3 C2 118.90(13) . . ?
F1 C3 C4 117.97(13) . . ?
C2 C3 C4 123.12(14) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 C6 118.77(14) . . ?
C4 C5 H5 120.6 . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.44(13) . . ?
C3 C2 H2 120.8 . . ?
C10 C11 H11 120.7 . . ?
C10 C11 C12 118.51(14) . . ?
C12 C11 H11 120.7 . . ?
C10 C15 N1 109.96(12) . . ?
C14 C15 N1 127.70(13) . . ?
C14 C15 C10 122.33(14) . . ?
O2 C7 H7 117.2 . . ?
C8 C7 O2 125.59(13) . . ?
C8 C7 H7 117.2 . . ?
C11 C10 C15 120.03(13) . . ?
C11 C10 C9 131.09(13) . . ?
C15 C10 C9 108.86(12) . . ?
C15 C14 H14 121.4 . . ?
C15 C14 C13 117.16(14) . . ?
C13 C14 H14 121.4 . . ?
C8 C9 C16 110.94(11) . . ?
C8 C9 C10 112.82(12) . . ?
C8 C9 C19 114.09(12) . . ?
C10 C9 C16 101.50(11) . . ?
C10 C9 C19 109.67(11) . . ?
C19 C9 C16 106.94(12) . . ?
O4 C19 C9 113.45(12) . . ?
O4 C19 H19A 108.9 . . ?
O4 C19 H19B 108.9 . . ?
C9 C19 H19A 108.9 . . ?
C9 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.48(14) . . ?
C13 C12 H12 119.8 . . ?
C3 C4 H4A 120.5 . . ?
C5 C4 C3 118.97(14) . . ?
C5 C4 H4A 120.5 . . ?
C14 C13 H13 119.3 . . ?
C12 C13 C14 121.45(14) . . ?
C12 C13 H13 119.3 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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 C3 C2 C1 179.56(12) . . . . ?
F1 C3 C4 C5 -179.88(13) . . . . ?
O2 C6 C5 C4 179.27(13) . . . . ?
O3 C16 C9 C8 59.75(19) . . . . ?
O3 C16 C9 C10 179.86(14) . . . . ?
O3 C16 C9 C19 -65.24(18) . . . . ?
N1 C16 C9 C8 -124.12(13) . . . . ?
N1 C16 C9 C10 -4.01(15) . . . . ?
N1 C16 C9 C19 110.89(13) . . . . ?
N1 C15 C10 C11 -177.77(13) . . . . ?
N1 C15 C10 C9 0.83(16) . . . . ?
N1 C15 C14 C13 178.40(14) . . . . ?
C1 C6 C5 C4 -1.2(2) . . . . ?
C8 C9 C19 O4 -55.36(17) . . . . ?
C18 C1 C6 O2 2.0(2) . . . . ?
C18 C1 C6 C5 -177.49(13) . . . . ?
C18 C1 C2 C3 178.93(13) . . . . ?
C18 C8 C7 O2 1.8(2) . . . . ?
C18 C8 C9 C16 45.36(17) . . . . ?
C18 C8 C9 C10 -67.76(16) . . . . ?
C18 C8 C9 C19 166.21(12) . . . . ?
C16 N1 C15 C10 -3.67(17) . . . . ?
C16 N1 C15 C14 176.65(15) . . . . ?
C16 C9 C19 O4 67.70(15) . . . . ?
C6 O2 C7 C8 -0.1(2) . . . . ?
C6 C1 C18 O1 179.08(13) . . . . ?
C6 C1 C18 C8 -0.35(19) . . . . ?
C6 C1 C2 C3 0.5(2) . . . . ?
C6 C5 C4 C3 0.1(2) . . . . ?
C2 C1 C18 O1 0.7(2) . . . . ?
C2 C1 C18 C8 -178.70(13) . . . . ?
C2 C1 C6 O2 -179.63(12) . . . . ?
C2 C1 C6 C5 0.9(2) . . . . ?
C2 C3 C4 C5 1.4(2) . . . . ?
C11 C10 C9 C8 -61.0(2) . . . . ?
C11 C10 C9 C16 -179.74(15) . . . . ?
C11 C10 C9 C19 67.4(2) . . . . ?
C11 C12 C13 C14 1.0(2) . . . . ?
C15 N1 C16 O3 -179.06(14) . . . . ?
C15 N1 C16 C9 4.84(16) . . . . ?
C15 C10 C9 C8 120.65(13) . . . . ?
C15 C10 C9 C16 1.87(15) . . . . ?
C15 C10 C9 C19 -110.99(13) . . . . ?
C15 C14 C13 C12 -0.2(2) . . . . ?
C7 O2 C6 C1 -1.8(2) . . . . ?
C7 O2 C6 C5 177.72(12) . . . . ?
C7 C8 C18 O1 179.13(14) . . . . ?
C7 C8 C18 C1 -1.45(19) . . . . ?
C7 C8 C9 C16 -135.92(14) . . . . ?
C7 C8 C9 C10 110.97(15) . . . . ?
C7 C8 C9 C19 -15.06(19) . . . . ?
C10 C11 C12 C13 -0.4(2) . . . . ?
C10 C15 C14 C13 -1.2(2) . . . . ?
C10 C9 C19 O4 176.98(12) . . . . ?
C14 C15 C10 C11 1.9(2) . . . . ?
C14 C15 C10 C9 -179.48(14) . . . . ?
C9 C8 C18 O1 -2.1(2) . . . . ?
C9 C8 C18 C1 177.32(12) . . . . ?
C9 C8 C7 O2 -176.93(13) . . . . ?
C12 C11 C10 C15 -1.1(2) . . . . ?
C12 C11 C10 C9 -179.31(15) . . . . ?
C4 C3 C2 C1 -1.7(2) . . . . ?
C17 N1 C16 O3 -7.0(2) . . . . ?
C17 N1 C16 C9 176.89(13) . . . . ?
C17 N1 C15 C10 -175.78(13) . . . . ?
C17 N1 C15 C14 4.5(2) . . . . ?

_olex2_date_sample_data_collection 2017-11-11
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.176
_oxdiff_exptl_absorpt_empirical_full_min 0.801
####################################################################### 
# 
# 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_mo_gd_lxl32_0m
_database_code_depnum_ccdc_archive 'CCDC 1944915'
loop_
_audit_author_name
_audit_author_address
'Xiong-Li Liu'
;guizhou university
China
;
_audit_update_record             
;
2019-08-02 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H18 Br N O3'
_chemical_formula_sum            'C25 H18 Br N O3'
_chemical_formula_weight         460.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.2679(7)
_cell_length_b                   11.9073(8)
_cell_length_c                   18.5390(13)
_cell_angle_alpha                90
_cell_angle_beta                 102.7340(10)
_cell_angle_gamma                90
_cell_volume                     1995.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5501
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      28.81

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   0.1541
_exptl_transmission_factor_max   0.2134
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    2.088
_shelx_estimated_absorpt_T_min   0.481
_shelx_estimated_absorpt_T_max   0.731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22109
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.048
_diffrn_reflns_theta_max         31.084
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5922
_reflns_number_gt                4577
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0533P)²+0.4724P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5922
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.1022
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.39753(2) 0.10142(2) 1.05561(2) 0.02398(8) Uani 1 1 d . . . . .
O1 O 0.15865(16) 0.27066(13) 0.67864(8) 0.0220(3) Uani 1 1 d . . . . .
O2 O 0.31488(16) 0.52193(12) 0.82411(8) 0.0216(3) Uani 1 1 d . . . . .
O3 O 0.61307(16) 0.50923(12) 0.77472(8) 0.0202(3) Uani 1 1 d . . . . .
N1 N 0.65127(18) 0.47026(14) 0.89943(9) 0.0169(3) Uani 1 1 d . . . . .
C1 C -0.1662(2) 0.4478(2) 0.64297(12) 0.0261(5) Uani 1 1 d . . . . .
H1 H -0.2639 0.4473 0.6133 0.031 Uiso 1 1 calc R U . . .
C2 C -0.0730(2) 0.3588(2) 0.63862(12) 0.0246(5) Uani 1 1 d . . . . .
H18 H -0.1047 0.2977 0.6060 0.029 Uiso 1 1 calc R U . . .
C3 C 0.0699(2) 0.36133(18) 0.68388(12) 0.0198(4) Uani 1 1 d . . . . .
C4 C 0.2975(2) 0.26846(17) 0.72136(11) 0.0194(4) Uani 1 1 d . . . . .
H3 H 0.3580 0.2058 0.7163 0.023 Uiso 1 1 calc R U . . .
C5 C 0.3563(2) 0.34866(16) 0.77060(11) 0.0148(4) Uani 1 1 d . . . . .
C6 C 0.5096(2) 0.33808(15) 0.81896(11) 0.0142(4) Uani 1 1 d . . . . .
C7 C 0.6096(2) 0.25321(17) 0.78824(11) 0.0177(4) Uani 1 1 d . . . . .
H16 H 0.5598 0.1792 0.7812 0.021 Uiso 1 1 calc R U . . .
H17 H 0.6219 0.2796 0.7393 0.021 Uiso 1 1 calc R U . . .
C8 C 0.7615(2) 0.23934(17) 0.83919(11) 0.0170(4) Uani 1 1 d . . . . .
C9 C 0.8761(2) 0.31278(18) 0.83576(12) 0.0203(4) Uani 1 1 d . . . . .
H15 H 0.8625 0.3690 0.7985 0.024 Uiso 1 1 calc R U . . .
C10 C 1.0120(2) 0.3044(2) 0.88692(13) 0.0262(5) Uani 1 1 d . . . . .
H12 H 1.0897 0.3556 0.8849 0.031 Uiso 1 1 calc R U . . .
C11 C 1.0320(3) 0.2212(2) 0.94038(13) 0.0311(5) Uani 1 1 d . . . . .
H2 H 1.1236 0.2155 0.9753 0.037 Uiso 1 1 calc R U . . .
C12 C 0.2683(2) 0.44719(17) 0.77950(11) 0.0158(4) Uani 1 1 d . . . . .
C13 C 0.1182(2) 0.44981(17) 0.73150(11) 0.0171(4) Uani 1 1 d . . . . .
C14 C 0.0216(2) 0.53934(18) 0.73457(12) 0.0198(4) Uani 1 1 d . . . . .
H4 H 0.0530 0.6006 0.7671 0.024 Uiso 1 1 calc R U . . .
C15 C -0.1199(2) 0.5385(2) 0.69012(12) 0.0243(5) Uani 1 1 d . . . . .
H5 H -0.1852 0.5995 0.6917 0.029 Uiso 1 1 calc R U . . .
C16 C 0.5930(2) 0.45170(16) 0.82607(11) 0.0162(4) Uani 1 1 d . . . . .
C17 C 0.7601(2) 0.55653(18) 0.92813(13) 0.0248(5) Uani 1 1 d . . . . .
H6 H 0.7925 0.5928 0.8870 0.037 Uiso 1 1 calc R U . . .
H7 H 0.8453 0.5221 0.9616 0.037 Uiso 1 1 calc R U . . .
H8 H 0.7156 0.6127 0.9552 0.037 Uiso 1 1 calc R U . . .
C18 C 0.6016(2) 0.39077(16) 0.94386(11) 0.0161(4) Uani 1 1 d . . . . .
C19 C 0.6332(2) 0.38534(17) 1.02006(12) 0.0198(4) Uani 1 1 d . . . . .
H11 H 0.6951 0.4395 1.0494 0.024 Uiso 1 1 calc R U . . .
C20 C 0.5708(2) 0.29725(18) 1.05247(12) 0.0212(4) Uani 1 1 d . . . . .
H10 H 0.5901 0.2907 1.1048 0.025 Uiso 1 1 calc R U . . .
C21 C 0.4809(2) 0.21941(17) 1.00851(12) 0.0189(4) Uani 1 1 d . . . . .
C22 C 0.4486(2) 0.22533(17) 0.93140(11) 0.0162(4) Uani 1 1 d . . . . .
H9 H 0.3862 0.1715 0.9020 0.019 Uiso 1 1 calc R U . . .
C23 C 0.5108(2) 0.31257(16) 0.89929(10) 0.0139(4) Uani 1 1 d . . . . .
C24 C 0.9194(3) 0.1462(2) 0.94318(13) 0.0295(5) Uani 1 1 d . . . . .
H14 H 0.9338 0.0889 0.9797 0.035 Uiso 1 1 calc R U . . .
C25 C 0.7848(2) 0.15515(19) 0.89231(13) 0.0237(5) Uani 1 1 d . . . . .
H13 H 0.7080 0.1030 0.8940 0.028 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C21 1.906(2) . ?
O1 C4 1.355(2) . ?
O1 C3 1.374(3) . ?
O2 C12 1.227(2) . ?
O3 C16 1.220(2) . ?
N1 C16 1.366(3) . ?
N1 C18 1.398(3) . ?
N1 C17 1.456(3) . ?
C1 C2 1.381(3) . ?
C1 C15 1.397(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.403(3) . ?
C2 H18 0.9500 . ?
C3 C13 1.384(3) . ?
C4 C5 1.350(3) . ?
C4 H3 0.9500 . ?
C5 C12 1.459(3) . ?
C5 C6 1.509(3) . ?
C6 C23 1.518(3) . ?
C6 C16 1.549(3) . ?
C6 C7 1.561(3) . ?
C7 C8 1.521(3) . ?
C7 H16 0.9900 . ?
C7 H17 0.9900 . ?
C8 C25 1.389(3) . ?
C8 C9 1.388(3) . ?
C9 C10 1.403(3) . ?
C9 H15 0.9500 . ?
C10 C11 1.385(3) . ?
C10 H12 0.9500 . ?
C11 C24 1.383(4) . ?
C11 H2 0.9500 . ?
C12 C13 1.477(3) . ?
C13 C14 1.402(3) . ?
C14 C15 1.386(3) . ?
C14 H4 0.9500 . ?
C15 H5 0.9500 . ?
C17 H6 0.9800 . ?
C17 H7 0.9800 . ?
C17 H8 0.9800 . ?
C18 C19 1.380(3) . ?
C18 C23 1.397(3) . ?
C19 C20 1.396(3) . ?
C19 H11 0.9500 . ?
C20 C21 1.385(3) . ?
C20 H10 0.9500 . ?
C21 C22 1.396(3) . ?
C22 C23 1.385(3) . ?
C22 H9 0.9500 . ?
C24 C25 1.392(3) . ?
C24 H14 0.9500 . ?
C25 H13 0.9500 . ?

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
C4 O1 C3 118.72(16) . . ?
C16 N1 C18 111.60(16) . . ?
C16 N1 C17 124.61(18) . . ?
C18 N1 C17 123.64(17) . . ?
C2 C1 C15 121.4(2) . . ?
C2 C1 H1 119.3 . . ?
C15 C1 H1 119.3 . . ?
C1 C2 C3 117.9(2) . . ?
C1 C2 H18 121.0 . . ?
C3 C2 H18 121.0 . . ?
O1 C3 C13 121.90(18) . . ?
O1 C3 C2 116.21(19) . . ?
C13 C3 C2 121.9(2) . . ?
C5 C4 O1 124.84(19) . . ?
C5 C4 H3 117.6 . . ?
O1 C4 H3 117.6 . . ?
C4 C5 C12 119.55(18) . . ?
C4 C5 C6 121.97(18) . . ?
C12 C5 C6 118.46(17) . . ?
C5 C6 C23 113.69(16) . . ?
C5 C6 C16 111.38(15) . . ?
C23 C6 C16 101.29(15) . . ?
C5 C6 C7 113.23(16) . . ?
C23 C6 C7 110.61(16) . . ?
C16 C6 C7 105.72(15) . . ?
C8 C7 C6 112.72(16) . . ?
C8 C7 H16 109.0 . . ?
C6 C7 H16 109.0 . . ?
C8 C7 H17 109.0 . . ?
C6 C7 H17 109.0 . . ?
H16 C7 H17 107.8 . . ?
C25 C8 C9 119.1(2) . . ?
C25 C8 C7 119.81(19) . . ?
C9 C8 C7 121.06(18) . . ?
C8 C9 C10 120.4(2) . . ?
C8 C9 H15 119.8 . . ?
C10 C9 H15 119.8 . . ?
C11 C10 C9 119.6(2) . . ?
C11 C10 H12 120.2 . . ?
C9 C10 H12 120.2 . . ?
C24 C11 C10 120.3(2) . . ?
C24 C11 H2 119.8 . . ?
C10 C11 H2 119.8 . . ?
O2 C12 C5 122.51(18) . . ?
O2 C12 C13 122.37(18) . . ?
C5 C12 C13 115.11(17) . . ?
C3 C13 C14 119.00(19) . . ?
C3 C13 C12 119.85(18) . . ?
C14 C13 C12 121.13(19) . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H4 120.0 . . ?
C13 C14 H4 120.0 . . ?
C14 C15 C1 119.8(2) . . ?
C14 C15 H5 120.1 . . ?
C1 C15 H5 120.1 . . ?
O3 C16 N1 126.25(18) . . ?
O3 C16 C6 125.66(18) . . ?
N1 C16 C6 107.83(16) . . ?
N1 C17 H6 109.5 . . ?
N1 C17 H7 109.5 . . ?
H6 C17 H7 109.5 . . ?
N1 C17 H8 109.5 . . ?
H6 C17 H8 109.5 . . ?
H7 C17 H8 109.5 . . ?
C19 C18 N1 127.75(18) . . ?
C19 C18 C23 122.59(19) . . ?
N1 C18 C23 109.66(17) . . ?
C18 C19 C20 117.48(19) . . ?
C18 C19 H11 121.3 . . ?
C20 C19 H11 121.3 . . ?
C21 C20 C19 120.14(19) . . ?
C21 C20 H10 119.9 . . ?
C19 C20 H10 119.9 . . ?
C20 C21 C22 122.29(19) . . ?
C20 C21 Br1 118.42(16) . . ?
C22 C21 Br1 119.29(16) . . ?
C23 C22 C21 117.54(19) . . ?
C23 C22 H9 121.2 . . ?
C21 C22 H9 121.2 . . ?
C22 C23 C18 119.96(18) . . ?
C22 C23 C6 131.18(18) . . ?
C18 C23 C6 108.66(17) . . ?
C11 C24 C25 119.8(2) . . ?
C11 C24 H14 120.1 . . ?
C25 C24 H14 120.1 . . ?
C8 C25 C24 120.8(2) . . ?
C8 C25 H13 119.6 . . ?
C24 C25 H13 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 C1 C2 C3 0.8(3) . . . . ?
C4 O1 C3 C13 -0.1(3) . . . . ?
C4 O1 C3 C2 -179.69(19) . . . . ?
C1 C2 C3 O1 179.2(2) . . . . ?
C1 C2 C3 C13 -0.3(3) . . . . ?
C3 O1 C4 C5 1.2(3) . . . . ?
O1 C4 C5 C12 -0.9(3) . . . . ?
O1 C4 C5 C6 177.10(19) . . . . ?
C4 C5 C6 C23 -106.7(2) . . . . ?
C12 C5 C6 C23 71.3(2) . . . . ?
C4 C5 C6 C16 139.60(19) . . . . ?
C12 C5 C6 C16 -42.4(2) . . . . ?
C4 C5 C6 C7 20.6(3) . . . . ?
C12 C5 C6 C7 -161.36(17) . . . . ?
C5 C6 C7 C8 -177.41(16) . . . . ?
C23 C6 C7 C8 -48.5(2) . . . . ?
C16 C6 C7 C8 60.4(2) . . . . ?
C6 C7 C8 C25 92.1(2) . . . . ?
C6 C7 C8 C9 -85.1(2) . . . . ?
C25 C8 C9 C10 -2.2(3) . . . . ?
C7 C8 C9 C10 174.93(19) . . . . ?
C8 C9 C10 C11 1.0(3) . . . . ?
C9 C10 C11 C24 0.4(4) . . . . ?
C4 C5 C12 O2 178.87(19) . . . . ?
C6 C5 C12 O2 0.8(3) . . . . ?
C4 C5 C12 C13 -0.4(3) . . . . ?
C6 C5 C12 C13 -178.49(16) . . . . ?
O1 C3 C13 C14 -179.48(19) . . . . ?
C2 C3 C13 C14 0.0(3) . . . . ?
O1 C3 C13 C12 -1.2(3) . . . . ?
C2 C3 C13 C12 178.4(2) . . . . ?
O2 C12 C13 C3 -177.9(2) . . . . ?
C5 C12 C13 C3 1.4(3) . . . . ?
O2 C12 C13 C14 0.4(3) . . . . ?
C5 C12 C13 C14 179.68(18) . . . . ?
C3 C13 C14 C15 -0.2(3) . . . . ?
C12 C13 C14 C15 -178.53(19) . . . . ?
C13 C14 C15 C1 0.7(3) . . . . ?
C2 C1 C15 C14 -1.0(3) . . . . ?
C18 N1 C16 O3 177.74(18) . . . . ?
C17 N1 C16 O3 -6.6(3) . . . . ?
C18 N1 C16 C6 -7.8(2) . . . . ?
C17 N1 C16 C6 167.84(18) . . . . ?
C5 C6 C16 O3 -54.7(3) . . . . ?
C23 C6 C16 O3 -175.88(18) . . . . ?
C7 C6 C16 O3 68.7(2) . . . . ?
C5 C6 C16 N1 130.87(17) . . . . ?
C23 C6 C16 N1 9.66(19) . . . . ?
C7 C6 C16 N1 -105.75(17) . . . . ?
C16 N1 C18 C19 -177.72(19) . . . . ?
C17 N1 C18 C19 6.6(3) . . . . ?
C16 N1 C18 C23 2.3(2) . . . . ?
C17 N1 C18 C23 -173.40(18) . . . . ?
N1 C18 C19 C20 -179.77(19) . . . . ?
C23 C18 C19 C20 0.2(3) . . . . ?
C18 C19 C20 C21 -0.1(3) . . . . ?
C19 C20 C21 C22 -0.2(3) . . . . ?
C19 C20 C21 Br1 -179.58(16) . . . . ?
C20 C21 C22 C23 0.4(3) . . . . ?
Br1 C21 C22 C23 179.72(14) . . . . ?
C21 C22 C23 C18 -0.2(3) . . . . ?
C21 C22 C23 C6 174.16(19) . . . . ?
C19 C18 C23 C22 0.0(3) . . . . ?
N1 C18 C23 C22 179.92(17) . . . . ?
C19 C18 C23 C6 -175.59(18) . . . . ?
N1 C18 C23 C6 4.4(2) . . . . ?
C5 C6 C23 C22 57.2(3) . . . . ?
C16 C6 C23 C22 176.8(2) . . . . ?
C7 C6 C23 C22 -71.5(3) . . . . ?
C5 C6 C23 C18 -127.91(17) . . . . ?
C16 C6 C23 C18 -8.34(19) . . . . ?
C7 C6 C23 C18 103.39(18) . . . . ?
C10 C11 C24 C25 -0.5(4) . . . . ?
C9 C8 C25 C24 2.1(3) . . . . ?
C7 C8 C25 C24 -175.07(19) . . . . ?
C11 C24 C25 C8 -0.8(3) . . . . ?

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
C20 H10 O2 0.95 2.64 3.150(3) 114.0 3_667
C19 H11 O2 0.95 2.41 3.030(3) 122.5 3_667
C17 H6 O1 0.98 2.53 3.412(3) 149.4 2_656
C4 H3 O3 0.95 2.36 3.193(3) 146.4 2_646
C20 H10 O2 0.95 2.64 3.150(3) 114.0 3_667
C19 H11 O2 0.95 2.41 3.030(3) 122.5 3_667
C17 H6 O1 0.98 2.53 3.412(3) 149.4 2_656
C4 H3 O3 0.95 2.36 3.193(3) 146.4 2_646
C20 H10 O2 0.95 2.64 3.150(3) 114.0 3_667
C19 H11 O2 0.95 2.41 3.030(3) 122.5 3_667
C17 H6 O1 0.98 2.53 3.412(3) 149.4 2_656
C4 H3 O3 0.95 2.36 3.193(3) 146.4 2_646
C20 H10 O2 0.95 2.64 3.150(3) 114.0 3_667
C19 H11 O2 0.95 2.41 3.030(3) 122.5 3_667
C17 H6 O1 0.98 2.53 3.412(3) 149.4 2_656
C4 H3 O3 0.95 2.36 3.193(3) 146.4 2_646
C4 H3 O3 0.95 2.36 3.193(3) 146.4 2_646
C17 H6 O1 0.98 2.53 3.412(3) 149.4 2_656
C19 H11 O2 0.95 2.41 3.030(3) 122.5 3_667
C20 H10 O2 0.95 2.64 3.150(3) 114.0 3_667
C4 H3 O3 0.95 2.36 3.193(3) 146.4 2_646
C17 H6 O1 0.98 2.53 3.412(3) 149.4 2_656
C19 H11 O2 0.95 2.41 3.030(3) 122.5 3_667
C20 H10 O2 0.95 2.64 3.150(3) 114.0 3_667
C4 H3 O3 0.95 2.36 3.193(3) 146.4 2_646
C17 H6 O1 0.98 2.53 3.412(3) 149.4 2_656
C19 H11 O2 0.95 2.41 3.030(3) 122.5 3_667
C20 H10 O2 0.95 2.64 3.150(3) 114.0 3_667

_refine_diff_density_max         0.728
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.087

####################################################################### 
# 
# 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_my-4
_database_code_depnum_ccdc_archive 'CCDC 1843646'
loop_
_audit_author_name
_audit_author_address
'Xiong-Li Liu'
;guizhou university
China
;
_audit_update_record             
;
2018-05-16 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;
_audit_creation_date             2017-11-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 N O4'
_chemical_formula_sum            'C20 H17 N O4'
_chemical_formula_weight         335.35
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.0065(5)
_cell_length_b                   11.3472(6)
_cell_length_c                   15.5009(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.690(5)
_cell_angle_gamma                90
_cell_volume                     1556.68(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4221
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.9360
_cell_measurement_theta_min      3.6920
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.06173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.885
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11973
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.511
_diffrn_reflns_theta_min         3.384
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00  60.00   1.00    2.00    --  -11.59  57.00-120.00  100
  2  ω     42.00  68.00   1.00    2.00    --   11.74 178.00  90.00   26
  3  ω    -83.00  11.00   1.00    2.00    --  -11.59 -57.00  90.00   94
  4  ω    -74.00   7.00   1.00    2.00    --  -11.59 -77.00 -30.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0547180000
_diffrn_orient_matrix_UB_12      -0.0312053000
_diffrn_orient_matrix_UB_13      0.0302810000
_diffrn_orient_matrix_UB_21      -0.0522828000
_diffrn_orient_matrix_UB_22      -0.0466283000
_diffrn_orient_matrix_UB_23      0.0006207000
_diffrn_orient_matrix_UB_31      0.0264139000
_diffrn_orient_matrix_UB_32      -0.0275904000
_diffrn_orient_matrix_UB_33      -0.0353432000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3028
_reflns_number_total             3851
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3851
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0484
_refine_ls_restrained_S_all      1.039
_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)+(0.0469P)²+0.6187P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1208
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C14(H14), C9(H9), C17(H17), C2(H2), C16(H16), C4(H4), C3(H3A)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.86974(12) 0.54085(10) 0.61757(7) 0.0182(2) Uani 1 1 d . . . . .
O2 O 0.54700(12) 0.34102(10) 0.70170(7) 0.0207(3) Uani 1 1 d . . . . .
O4 O 0.77003(13) 0.29845(10) 0.88173(8) 0.0230(3) Uani 1 1 d . . . . .
O3 O 0.98612(12) 0.48715(11) 0.89382(8) 0.0259(3) Uani 1 1 d . . . . .
H3 H 0.967724 0.418166 0.903591 0.039 Uiso 1 1 calc GR . . . .
N005 N 0.54865(14) 0.39203(11) 0.89701(8) 0.0161(3) Uani 1 1 d . . . . .
C6 C 0.65850(16) 0.40692(13) 0.58278(10) 0.0151(3) Uani 1 1 d . . . . .
C7 C 0.64068(16) 0.40464(13) 0.67538(10) 0.0151(3) Uani 1 1 d . . . . .
C5 C 0.55980(17) 0.34545(13) 0.51723(10) 0.0171(3) Uani 1 1 d . . . . .
H5 H 0.483419 0.299066 0.532330 0.021 Uiso 1 1 calc R . . . .
C12 C 0.47900(17) 0.50123(13) 0.87215(10) 0.0151(3) Uani 1 1 d . . . . .
C14 C 0.52942(17) 0.68069(13) 0.79972(10) 0.0159(3) Uani 1 1 d . . . . .
H14 H 0.593453 0.726689 0.773021 0.019 Uiso 1 1 calc R . . . .
C1 C 0.77037(17) 0.47587(13) 0.55761(10) 0.0159(3) Uani 1 1 d . . . . .
C8 C 0.74099(16) 0.48435(13) 0.73316(10) 0.0150(3) Uani 1 1 d . . . . .
C9 C 0.84688(17) 0.54522(14) 0.70133(10) 0.0171(3) Uani 1 1 d . . . . .
H9 H 0.909606 0.594394 0.740054 0.021 Uiso 1 1 calc R . . . .
C13 C 0.57340(16) 0.56947(13) 0.83037(10) 0.0150(3) Uani 1 1 d . . . . .
C17 C 0.33859(17) 0.54101(14) 0.88281(10) 0.0175(3) Uani 1 1 d . . . . .
H17 H 0.275844 0.495018 0.910442 0.021 Uiso 1 1 calc R . . . .
C11 C 0.68311(17) 0.38263(14) 0.86914(10) 0.0170(3) Uani 1 1 d . . . . .
C10 C 0.71588(16) 0.50045(13) 0.82673(10) 0.0148(3) Uani 1 1 d . . . . .
C2 C 0.78826(17) 0.48504(14) 0.47036(10) 0.0185(3) Uani 1 1 d . . . . .
H2 H 0.864634 0.531228 0.455039 0.022 Uiso 1 1 calc R . . . .
C16 C 0.29455(17) 0.65309(14) 0.85045(10) 0.0180(3) Uani 1 1 d . . . . .
H16 H 0.200244 0.681520 0.856637 0.022 Uiso 1 1 calc R . . . .
C15 C 0.38712(17) 0.72381(13) 0.80920(10) 0.0172(3) Uani 1 1 d . . . . .
C4 C 0.57556(18) 0.35353(14) 0.43060(10) 0.0190(3) Uani 1 1 d . . . . .
H4 H 0.510287 0.312231 0.387559 0.023 Uiso 1 1 calc R . . . .
C3 C 0.68958(18) 0.42374(14) 0.40744(10) 0.0195(3) Uani 1 1 d . . . . .
H3A H 0.699025 0.429185 0.348836 0.023 Uiso 1 1 calc R . . . .
C19 C 0.33491(18) 0.84375(14) 0.77315(11) 0.0213(3) Uani 1 1 d . . . . .
H19A H 0.391136 0.903904 0.808637 0.032 Uiso 1 1 calc GR . . . .
H19B H 0.229254 0.852932 0.774064 0.032 Uiso 1 1 calc GR . . . .
H19C H 0.351210 0.850522 0.713882 0.032 Uiso 1 1 calc GR . . . .
C20 C 0.85289(17) 0.55526(15) 0.88857(10) 0.0191(3) Uani 1 1 d . . . . .
H20A H 0.870979 0.633616 0.867737 0.023 Uiso 1 1 calc R . . . .
H20B H 0.829238 0.563065 0.946858 0.023 Uiso 1 1 calc R . . . .
C18 C 0.47855(19) 0.29638(14) 0.93661(11) 0.0209(3) Uani 1 1 d . . . . .
H18A H 0.445145 0.324448 0.988231 0.031 Uiso 1 1 calc GR . . . .
H18B H 0.550534 0.234044 0.952389 0.031 Uiso 1 1 calc GR . . . .
H18C H 0.393513 0.267237 0.895459 0.031 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 C1 1.3784(18) . ?
O1 C9 1.3527(18) . ?
O2 C7 1.2357(18) . ?
O4 C11 1.2275(18) . ?
O3 H3 0.8200 . ?
O3 C20 1.4169(19) . ?
N005 C12 1.4098(19) . ?
N005 C11 1.363(2) . ?
N005 C18 1.4482(19) . ?
C6 C7 1.474(2) . ?
C6 C5 1.405(2) . ?
C6 C1 1.388(2) . ?
C7 C8 1.462(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.379(2) . ?
C12 C13 1.395(2) . ?
C12 C17 1.381(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.380(2) . ?
C14 C15 1.405(2) . ?
C1 C2 1.395(2) . ?
C8 C9 1.343(2) . ?
C8 C10 1.520(2) . ?
C9 H9 0.9300 . ?
C13 C10 1.513(2) . ?
C17 H17 0.9300 . ?
C17 C16 1.397(2) . ?
C11 C10 1.542(2) . ?
C10 C20 1.546(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(2) . ?
C16 H16 0.9300 . ?
C16 C15 1.395(2) . ?
C15 C19 1.513(2) . ?
C4 H4 0.9300 . ?
C4 C3 1.398(2) . ?
C3 H3A 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C9 O1 C1 118.13(12) . . ?
C20 O3 H3 109.5 . . ?
C12 N005 C18 124.59(13) . . ?
C11 N005 C12 111.01(12) . . ?
C11 N005 C18 123.94(13) . . ?
C5 C6 C7 121.81(14) . . ?
C1 C6 C7 119.98(13) . . ?
C1 C6 C5 118.13(14) . . ?
O2 C7 C6 122.42(14) . . ?
O2 C7 C8 122.78(14) . . ?
C8 C7 C6 114.79(13) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.37(14) . . ?
C4 C5 H5 119.8 . . ?
C13 C12 N005 109.64(13) . . ?
C17 C12 N005 128.71(14) . . ?
C17 C12 C13 121.63(14) . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.44(14) . . ?
C15 C14 H14 120.3 . . ?
O1 C1 C6 121.77(13) . . ?
O1 C1 C2 115.88(13) . . ?
C6 C1 C2 122.35(14) . . ?
C7 C8 C10 118.34(13) . . ?
C9 C8 C7 119.57(14) . . ?
C9 C8 C10 122.01(13) . . ?
O1 C9 H9 117.3 . . ?
C8 C9 O1 125.34(14) . . ?
C8 C9 H9 117.3 . . ?
C12 C13 C10 108.91(13) . . ?
C14 C13 C12 120.43(14) . . ?
C14 C13 C10 130.66(13) . . ?
C12 C17 H17 121.3 . . ?
C12 C17 C16 117.37(14) . . ?
C16 C17 H17 121.3 . . ?
O4 C11 N005 126.04(14) . . ?
O4 C11 C10 125.13(14) . . ?
N005 C11 C10 108.59(12) . . ?
C8 C10 C11 112.13(12) . . ?
C8 C10 C20 113.40(12) . . ?
C13 C10 C8 112.03(12) . . ?
C13 C10 C11 101.66(12) . . ?
C13 C10 C20 110.70(12) . . ?
C11 C10 C20 106.16(12) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.20(14) . . ?
C3 C2 H2 120.9 . . ?
C17 C16 H16 118.9 . . ?
C15 C16 C17 122.29(14) . . ?
C15 C16 H16 118.9 . . ?
C14 C15 C19 120.12(14) . . ?
C16 C15 C14 118.82(14) . . ?
C16 C15 C19 121.04(14) . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.07(15) . . ?
C3 C4 H4 120.0 . . ?
C2 C3 C4 120.88(15) . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 H3A 119.6 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O3 C20 C10 112.72(13) . . ?
O3 C20 H20A 109.0 . . ?
O3 C20 H20B 109.0 . . ?
C10 C20 H20A 109.0 . . ?
C10 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
N005 C18 H18A 109.5 . . ?
N005 C18 H18B 109.5 . . ?
N005 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 10.460
_oxdiff_exptl_absorpt_empirical_full_min 0.506
####################################################################### 
# 
# 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_my16_3
_database_code_depnum_ccdc_archive 'CCDC 1843647'
loop_
_audit_author_name
_audit_author_address
'Xiong-Li Liu'
;guizhou university
China
;
_audit_update_record             
;
2018-05-16 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;
_audit_creation_date             2017-11-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H14 Cl N O4'
_chemical_formula_sum            'C19 H14 Cl N O4'
_chemical_formula_weight         355.76
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   14.9389(9)
_cell_length_b                   6.8341(3)
_cell_length_c                   15.4499(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.164(6)
_cell_angle_gamma                90
_cell_volume                     1565.03(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3804
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.3860
_cell_measurement_theta_min      5.7280
_shelx_estimated_absorpt_T_max   0.779
_shelx_estimated_absorpt_T_min   0.716
_exptl_absorpt_coefficient_mu    2.389
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0983
_diffrn_reflns_av_unetI/netI     0.1131
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8148
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.643
_diffrn_reflns_theta_min         5.773
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  17.00   1.00    1.00    --  -40.73  57.00   0.00   83
  2  ω    -67.00  29.00   1.00    1.00    --  -40.73  57.00-150.00   96
  3  ω     10.00  51.00   1.00    1.00    --   40.73 -99.00 -90.00   41
  4  ω     72.00  97.00   1.00    1.00    --   40.73-125.00-180.00   25
  5  ω     35.00 110.00   1.00    3.00    --  106.95-125.00-180.00   75
  6  ω     84.00 133.00   1.00    3.00    --  106.95 -45.00-120.00   49
  7  ω    126.00 178.00   1.00    3.00    --  106.95  30.00 -30.00   52
  8  ω    112.00 172.00   1.00    3.00    --  106.95  30.00  30.00   60
  9  ω     98.00 166.00   1.00    3.00    --  106.95 125.00  30.00   68
 10  ω     80.00 170.00   1.00    3.00    --  106.95  30.00 120.00   90
 11  ω     89.00 122.00   1.00    3.00    --  106.95 -45.00 120.00   33
 12  ω     73.00 121.00   1.00    3.00    --  106.95-125.00 120.00   48
 13  ω     36.00 112.00   1.00    3.00    --  106.95 -45.00   0.00   76
 14  ω     38.00  63.00   1.00    3.00    --  106.95 -45.00-120.00   25
 15  ω     31.00 114.00   1.00    3.00    --  106.95 -77.00 -60.00   83
 16  ω     26.00  37.00   1.00    3.00    --  106.95 -94.00-150.00   11
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0933338000
_diffrn_orient_matrix_UB_12      -0.0213395000
_diffrn_orient_matrix_UB_13      0.0540970000
_diffrn_orient_matrix_UB_21      0.0387549000
_diffrn_orient_matrix_UB_22      0.1535891000
_diffrn_orient_matrix_UB_23      -0.0581179000
_diffrn_orient_matrix_UB_31      -0.0242087000
_diffrn_orient_matrix_UB_32      0.1635566000
_diffrn_orient_matrix_UB_33      0.0616802000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2573
_reflns_number_total             3069
_reflns_odcompleteness_completeness 98.82
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (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         1.100
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.143
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3069
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1291
_refine_ls_R_factor_gt           0.1081
_refine_ls_restrained_S_all      1.103
_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)+(0.1226P)²+8.4898P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2838
_refine_ls_wR_factor_ref         0.2927
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C14(H14), C15(H15), C2(H2), C5(H5), C12(H12), C4(H4A), C13(H13)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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
Cl01 Cl 0.62544(8) 0.89991(18) 0.68008(9) 0.0276(4) Uani 1 1 d . . . . .
O2 O 0.3772(2) 0.2636(5) 0.5669(2) 0.0218(8) Uani 1 1 d . . . . .
O3 O 0.0972(2) 0.2090(5) 0.4813(2) 0.0212(8) Uani 1 1 d . . . . .
O1 O 0.3014(2) 0.8178(5) 0.4897(2) 0.0208(8) Uani 1 1 d . . . . .
O4 O 0.0288(2) 0.6373(6) 0.4181(2) 0.0221(8) Uani 1 1 d . . . . .
H4 H -0.010187 0.683237 0.445039 0.033 Uiso 1 1 calc GR . . . .
N1 N 0.1170(3) 0.2470(6) 0.3373(3) 0.0188(9) Uani 1 1 d . . . . .
C7 C 0.2983(3) 0.2989(7) 0.5167(3) 0.0193(10) Uani 1 1 d . . . . .
H7 H 0.262401 0.191288 0.499172 0.023 Uiso 1 1 calc R . . . .
C19 C 0.3233(3) 0.6495(7) 0.5127(3) 0.0171(10) Uani 1 1 d . . . . .
C14 C 0.2251(4) 0.7055(8) 0.2108(3) 0.0225(11) Uani 1 1 d . . . . .
H14 H 0.247685 0.813819 0.184215 0.027 Uiso 1 1 calc R . . . .
C10 C 0.1257(3) 0.2992(7) 0.4223(3) 0.0179(10) Uani 1 1 d . . . . .
C15 C 0.2230(3) 0.7064(7) 0.3003(3) 0.0194(10) Uani 1 1 d . . . . .
H15 H 0.244154 0.813341 0.334057 0.023 Uiso 1 1 calc R . . . .
C6 C 0.4317(4) 0.4185(7) 0.5934(3) 0.0198(10) Uani 1 1 d . . . . .
C16 C 0.1884(3) 0.5431(7) 0.3379(3) 0.0169(10) Uani 1 1 d . . . . .
C11 C 0.1543(3) 0.3870(7) 0.2861(3) 0.0184(10) Uani 1 1 d . . . . .
C2 C 0.4689(3) 0.7619(7) 0.5948(3) 0.0207(11) Uani 1 1 d . . . . .
H2 H 0.455687 0.890303 0.577894 0.025 Uiso 1 1 calc R . . . .
C1 C 0.4086(3) 0.6087(7) 0.5675(3) 0.0163(10) Uani 1 1 d . . . . .
C9 C 0.1763(3) 0.4986(7) 0.4320(3) 0.0169(10) Uani 1 1 d . . . . .
C8 C 0.2668(3) 0.4767(7) 0.4897(3) 0.0168(10) Uani 1 1 d . . . . .
C5 C 0.5112(4) 0.3760(8) 0.6466(3) 0.0224(11) Uani 1 1 d . . . . .
H5 H 0.525123 0.247707 0.663215 0.027 Uiso 1 1 calc R . . . .
C12 C 0.1571(3) 0.3826(7) 0.1975(3) 0.0210(11) Uani 1 1 d . . . . .
H12 H 0.135375 0.275733 0.164013 0.025 Uiso 1 1 calc R . . . .
C4 C 0.5691(3) 0.5260(8) 0.6745(3) 0.0231(11) Uani 1 1 d . . . . .
H4A H 0.622051 0.500547 0.711203 0.028 Uiso 1 1 calc R . . . .
C18 C 0.1137(3) 0.6440(7) 0.4712(3) 0.0194(10) Uani 1 1 d . . . . .
H18A H 0.106869 0.607389 0.530683 0.023 Uiso 1 1 calc R . . . .
H18B H 0.138606 0.775109 0.471573 0.023 Uiso 1 1 calc R . . . .
C3 C 0.5476(4) 0.7171(8) 0.6470(3) 0.0215(11) Uani 1 1 d . . . . .
C13 C 0.1939(4) 0.5449(8) 0.1598(3) 0.0221(11) Uani 1 1 d . . . . .
H13 H 0.197639 0.546038 0.100203 0.026 Uiso 1 1 calc R . . . .
C17 C 0.0618(4) 0.0844(8) 0.3016(4) 0.0252(12) Uani 1 1 d . . . . .
H17A H 0.042155 0.009854 0.348369 0.038 Uiso 1 1 calc GR . . . .
H17B H 0.096632 0.002234 0.268032 0.038 Uiso 1 1 calc GR . . . .
H17C H 0.010234 0.133558 0.264747 0.038 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
Cl01 C3 1.739(5) . ?
O2 C7 1.349(6) . ?
O2 C6 1.367(6) . ?
O3 C10 1.220(6) . ?
O1 C19 1.236(6) . ?
O4 H4 0.8200 . ?
O4 C18 1.422(6) . ?
N1 C10 1.352(7) . ?
N1 C11 1.401(7) . ?
N1 C17 1.450(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.350(7) . ?
C19 C1 1.466(7) . ?
C19 C8 1.469(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.387(7) . ?
C14 C13 1.396(7) . ?
C10 C9 1.557(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.388(7) . ?
C6 C1 1.391(7) . ?
C6 C5 1.388(7) . ?
C16 C11 1.392(7) . ?
C16 C9 1.518(7) . ?
C11 C12 1.374(7) . ?
C2 H2 0.9300 . ?
C2 C1 1.411(7) . ?
C2 C3 1.374(7) . ?
C9 C8 1.532(7) . ?
C9 C18 1.539(7) . ?
C5 H5 0.9300 . ?
C5 C4 1.375(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.397(8) . ?
C4 H4A 0.9300 . ?
C4 C3 1.399(7) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C13 H13 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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 O2 C6 118.6(4) . . ?
C18 O4 H4 109.5 . . ?
C10 N1 C11 111.8(4) . . ?
C10 N1 C17 123.5(4) . . ?
C11 N1 C17 123.8(4) . . ?
O2 C7 H7 117.1 . . ?
O2 C7 C8 125.7(4) . . ?
C8 C7 H7 117.1 . . ?
O1 C19 C1 121.6(4) . . ?
O1 C19 C8 123.7(4) . . ?
C1 C19 C8 114.8(4) . . ?
C15 C14 H14 119.4 . . ?
C15 C14 C13 121.2(5) . . ?
C13 C14 H14 119.4 . . ?
O3 C10 N1 126.4(5) . . ?
O3 C10 C9 125.5(4) . . ?
N1 C10 C9 108.1(4) . . ?
C14 C15 H15 121.0 . . ?
C14 C15 C16 118.0(5) . . ?
C16 C15 H15 121.0 . . ?
O2 C6 C1 121.3(4) . . ?
O2 C6 C5 116.7(4) . . ?
C5 C6 C1 122.0(5) . . ?
C15 C16 C11 120.2(5) . . ?
C15 C16 C9 131.1(4) . . ?
C11 C16 C9 108.6(4) . . ?
C16 C11 N1 109.9(5) . . ?
C12 C11 N1 127.6(5) . . ?
C12 C11 C16 122.4(5) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C3 C2 C1 118.5(5) . . ?
C6 C1 C19 120.7(4) . . ?
C6 C1 C2 118.7(5) . . ?
C2 C1 C19 120.5(4) . . ?
C16 C9 C10 101.4(4) . . ?
C16 C9 C8 112.0(4) . . ?
C16 C9 C18 113.5(4) . . ?
C8 C9 C10 110.7(4) . . ?
C8 C9 C18 111.7(4) . . ?
C18 C9 C10 106.9(4) . . ?
C7 C8 C19 118.8(4) . . ?
C7 C8 C9 121.1(4) . . ?
C19 C8 C9 120.1(4) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 C6 119.2(5) . . ?
C4 C5 H5 120.4 . . ?
C11 C12 H12 121.3 . . ?
C11 C12 C13 117.4(5) . . ?
C13 C12 H12 121.3 . . ?
C5 C4 H4A 120.4 . . ?
C5 C4 C3 119.3(5) . . ?
C3 C4 H4A 120.4 . . ?
O4 C18 C9 107.1(4) . . ?
O4 C18 H18A 110.3 . . ?
O4 C18 H18B 110.3 . . ?
C9 C18 H18A 110.3 . . ?
C9 C18 H18B 110.3 . . ?
H18A C18 H18B 108.6 . . ?
C2 C3 Cl01 120.3(4) . . ?
C2 C3 C4 122.2(5) . . ?
C4 C3 Cl01 117.5(4) . . ?
C14 C13 C12 120.7(5) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
O2 C7 C8 C19 2.7(8) . . . . ?
O2 C7 C8 C9 179.4(5) . . . . ?
O2 C6 C1 C19 1.7(8) . . . . ?
O2 C6 C1 C2 -178.1(5) . . . . ?
O2 C6 C5 C4 179.3(5) . . . . ?
O3 C10 C9 C16 -176.3(5) . . . . ?
O3 C10 C9 C8 64.7(6) . . . . ?
O3 C10 C9 C18 -57.1(6) . . . . ?
O1 C19 C1 C6 179.4(5) . . . . ?
O1 C19 C1 C2 -0.7(8) . . . . ?
O1 C19 C8 C7 178.5(5) . . . . ?
O1 C19 C8 C9 1.8(7) . . . . ?
N1 C10 C9 C16 2.2(5) . . . . ?
N1 C10 C9 C8 -116.8(4) . . . . ?
N1 C10 C9 C18 121.3(4) . . . . ?
N1 C11 C12 C13 176.7(5) . . . . ?
C7 O2 C6 C1 -2.0(7) . . . . ?
C7 O2 C6 C5 178.5(5) . . . . ?
C14 C15 C16 C11 -2.1(7) . . . . ?
C14 C15 C16 C9 -179.6(5) . . . . ?
C10 N1 C11 C16 -1.2(6) . . . . ?
C10 N1 C11 C12 -179.6(5) . . . . ?
C10 C9 C8 C7 7.5(6) . . . . ?
C10 C9 C8 C19 -175.8(4) . . . . ?
C10 C9 C18 O4 -52.5(5) . . . . ?
C15 C14 C13 C12 1.9(8) . . . . ?
C15 C16 C11 N1 -175.4(4) . . . . ?
C15 C16 C11 C12 3.2(7) . . . . ?
C15 C16 C9 C10 174.8(5) . . . . ?
C15 C16 C9 C8 -67.1(7) . . . . ?
C15 C16 C9 C18 60.5(7) . . . . ?
C6 O2 C7 C8 -0.3(8) . . . . ?
C6 C5 C4 C3 -1.4(8) . . . . ?
C16 C11 C12 C13 -1.6(7) . . . . ?
C16 C9 C8 C7 -104.9(5) . . . . ?
C16 C9 C8 C19 71.8(6) . . . . ?
C16 C9 C18 O4 58.5(5) . . . . ?
C11 N1 C10 O3 177.7(5) . . . . ?
C11 N1 C10 C9 -0.8(5) . . . . ?
C11 C16 C9 C10 -2.9(5) . . . . ?
C11 C16 C9 C8 115.2(4) . . . . ?
C11 C16 C9 C18 -117.2(4) . . . . ?
C11 C12 C13 C14 -0.9(7) . . . . ?
C1 C19 C8 C7 -2.7(7) . . . . ?
C1 C19 C8 C9 -179.4(4) . . . . ?
C1 C6 C5 C4 -0.2(8) . . . . ?
C1 C2 C3 Cl01 178.3(4) . . . . ?
C1 C2 C3 C4 -0.7(8) . . . . ?
C9 C16 C11 N1 2.7(5) . . . . ?
C9 C16 C11 C12 -178.8(4) . . . . ?
C8 C19 C1 C6 0.6(7) . . . . ?
C8 C19 C1 C2 -179.6(4) . . . . ?
C8 C9 C18 O4 -173.8(4) . . . . ?
C5 C6 C1 C19 -178.7(5) . . . . ?
C5 C6 C1 C2 1.4(8) . . . . ?
C5 C4 C3 Cl01 -177.2(4) . . . . ?
C5 C4 C3 C2 1.9(8) . . . . ?
C18 C9 C8 C7 126.5(5) . . . . ?
C18 C9 C8 C19 -56.8(6) . . . . ?
C3 C2 C1 C19 179.2(5) . . . . ?
C3 C2 C1 C6 -0.9(8) . . . . ?
C13 C14 C15 C16 -0.4(7) . . . . ?
C17 N1 C10 O3 7.9(8) . . . . ?
C17 N1 C10 C9 -170.5(4) . . . . ?
C17 N1 C11 C16 168.6(4) . . . . ?
C17 N1 C11 C12 -9.9(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
;
_oxdiff_exptl_absorpt_empirical_full_max 1.902
_oxdiff_exptl_absorpt_empirical_full_min 0.257
####################################################################### 
# 
# 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_19
_database_code_depnum_ccdc_archive 'CCDC 1843650'
loop_
_audit_author_name
_audit_author_address
'Xiong-Li Liu'
;guizhou university
China
;
_audit_update_record             
;
2018-05-16 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;
_audit_creation_date             2017-11-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 Cl N O4'
_chemical_formula_sum            'C20 H16 Cl N O4'
_chemical_formula_weight         369.79
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.7526(6)
_cell_length_b                   29.898(2)
_cell_length_c                   8.2734(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.545(8)
_cell_angle_gamma                90
_cell_volume                     1670.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5231
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.1570
_cell_measurement_theta_min      3.9420
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.885
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17255
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.698
_diffrn_reflns_theta_min         3.200
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5368
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  29.00   0.50    2.19    --  -11.59 -19.00 -30.00   82
  2  ω     32.00  84.00   0.50    2.19    --   11.74  77.00 120.00  104
  3  ω    -21.00  27.00   0.50    2.19    --   11.74  77.00 120.00   96
  4  ω     31.00  57.00   0.50    2.19    --  -11.43  37.00 -90.00   52
  5  ω     -7.00  57.00   0.50    2.19    --   11.74  37.00  30.00  128
  6  ω    -32.00  48.00   0.50    2.00    --  -11.43  37.00-120.00  160
  7  ω    -18.00   9.00   0.50    2.00    --  -11.43 -99.00-120.00   54
  8  ω     54.00  80.00   0.50    2.00    --   11.74  37.00  30.00   52
  9  ω     32.00  65.00   0.50    2.00    --   11.74  37.00 150.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0362499000
_diffrn_orient_matrix_UB_12      0.0066118000
_diffrn_orient_matrix_UB_13      0.0765091000
_diffrn_orient_matrix_UB_21      -0.0067875000
_diffrn_orient_matrix_UB_22      0.0224155000
_diffrn_orient_matrix_UB_23      -0.0274720000
_diffrn_orient_matrix_UB_31      -0.0984616000
_diffrn_orient_matrix_UB_32      -0.0039905000
_diffrn_orient_matrix_UB_33      -0.0271712000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3250
_reflns_number_total             4195
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.655
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0588
_refine_ls_restrained_S_all      1.094
_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)+(0.0833P)²+0.7077P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1468
_refine_ls_wR_factor_ref         0.1718
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C2(H2), C7(H7), C5(H5), C4(H4), C15(H15), C14(H14)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.90838(9) 0.55165(2) 0.59430(9) 0.0385(2) Uani 1 1 d . . . . .
O3 O -0.1348(2) 0.37591(5) 0.9679(2) 0.0277(4) Uani 1 1 d . . . . .
H3 H -0.227155 0.358577 0.981990 0.042 Uiso 1 1 calc GR . . . .
O4 O 0.4939(2) 0.33982(5) 1.0029(2) 0.0282(4) Uani 1 1 d . . . . .
O2 O 0.1866(2) 0.48910(5) 0.9043(2) 0.0279(4) Uani 1 1 d . . . . .
O1 O 0.5146(2) 0.39526(5) 0.6711(2) 0.0271(4) Uani 1 1 d . . . . .
N1 N 0.3886(3) 0.30214(6) 0.7765(2) 0.0241(4) Uani 1 1 d . . . . .
C9 C 0.4193(3) 0.42337(6) 0.7450(3) 0.0209(5) Uani 1 1 d . . . . .
C17 C -0.0455(3) 0.35302(7) 0.6037(3) 0.0221(5) Uani 1 1 d . . . . .
H17 H -0.126927 0.376895 0.630988 0.027 Uiso 1 1 calc R . . . .
C1 C 0.4737(3) 0.47123(6) 0.7462(3) 0.0206(4) Uani 1 1 d . . . . .
C12 C 0.1156(3) 0.34246(6) 0.6991(3) 0.0205(5) Uani 1 1 d . . . . .
C13 C 0.2361(3) 0.30647(7) 0.6598(3) 0.0239(5) Uani 1 1 d . . . . .
C8 C 0.2466(3) 0.41224(6) 0.8411(3) 0.0197(4) Uani 1 1 d . . . . .
C16 C -0.0864(3) 0.32747(7) 0.4646(3) 0.0262(5) Uani 1 1 d . . . . .
C10 C 0.1902(3) 0.36308(6) 0.8558(3) 0.0201(4) Uani 1 1 d . . . . .
C11 C 0.3788(3) 0.33484(7) 0.8883(3) 0.0231(5) Uani 1 1 d . . . . .
C6 C 0.3538(3) 0.50182(7) 0.8246(3) 0.0229(5) Uani 1 1 d . . . . .
C2 C 0.6462(3) 0.48666(7) 0.6729(3) 0.0249(5) Uani 1 1 d . . . . .
H2 H 0.729540 0.466772 0.620189 0.030 Uiso 1 1 calc R . . . .
C20 C 0.0467(3) 0.35320(7) 0.9944(3) 0.0246(5) Uani 1 1 d . . . . .
H20A H 0.022771 0.321257 1.000749 0.030 Uiso 1 1 calc R . . . .
H20B H 0.105122 0.362823 1.096138 0.030 Uiso 1 1 calc R . . . .
C7 C 0.1414(3) 0.44493(7) 0.9124(3) 0.0242(5) Uani 1 1 d . . . . .
H7 H 0.030491 0.436671 0.971172 0.029 Uiso 1 1 calc R . . . .
C5 C 0.3988(3) 0.54735(7) 0.8279(3) 0.0269(5) Uani 1 1 d . . . . .
H5 H 0.315372 0.567439 0.879483 0.032 Uiso 1 1 calc R . . . .
C4 C 0.5672(3) 0.56208(7) 0.7543(3) 0.0276(5) Uani 1 1 d . . . . .
H4 H 0.598388 0.592378 0.754332 0.033 Uiso 1 1 calc R . . . .
C3 C 0.6920(3) 0.53145(7) 0.6791(3) 0.0265(5) Uani 1 1 d . . . . .
C15 C 0.0360(4) 0.29162(7) 0.4297(3) 0.0306(5) Uani 1 1 d . . . . .
H15 H 0.008064 0.274380 0.338752 0.037 Uiso 1 1 calc R . . . .
C14 C 0.1993(4) 0.28038(7) 0.5258(3) 0.0303(5) Uani 1 1 d . . . . .
H14 H 0.280146 0.256243 0.500344 0.036 Uiso 1 1 calc R . . . .
C18 C -0.2600(4) 0.33993(8) 0.3583(3) 0.0326(6) Uani 1 1 d . . . . .
H18A H -0.379872 0.338073 0.419366 0.049 Uiso 1 1 calc GR . . . .
H18B H -0.267589 0.319735 0.268203 0.049 Uiso 1 1 calc GR . . . .
H18C H -0.243246 0.369935 0.319370 0.049 Uiso 1 1 calc GR . . . .
C19 C 0.5544(4) 0.27141(8) 0.7620(3) 0.0345(6) Uani 1 1 d . . . . .
H19A H 0.505520 0.241870 0.739786 0.052 Uiso 1 1 calc GR . . . .
H19B H 0.629043 0.271140 0.861380 0.052 Uiso 1 1 calc GR . . . .
H19C H 0.638140 0.280921 0.675441 0.052 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
Cl1 C3 1.735(2) . ?
O3 H3 0.8200 . ?
O3 C20 1.416(3) . ?
O4 C11 1.229(3) . ?
O2 C6 1.367(3) . ?
O2 C7 1.357(2) . ?
O1 C9 1.225(3) . ?
N1 C13 1.411(3) . ?
N1 C11 1.348(3) . ?
N1 C19 1.454(3) . ?
C9 C1 1.477(3) . ?
C9 C8 1.456(3) . ?
C17 H17 0.9300 . ?
C17 C12 1.375(3) . ?
C17 C16 1.406(3) . ?
C1 C6 1.386(3) . ?
C1 C2 1.397(3) . ?
C12 C13 1.390(3) . ?
C12 C10 1.517(3) . ?
C13 C14 1.376(3) . ?
C8 C10 1.523(3) . ?
C8 C7 1.348(3) . ?
C16 C15 1.386(3) . ?
C16 C18 1.506(3) . ?
C10 C11 1.549(3) . ?
C10 C20 1.537(3) . ?
C6 C5 1.395(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C7 H7 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.368(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.395(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.395(3) . ?
C14 H14 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 O3 H3 109.5 . . ?
C7 O2 C6 118.79(18) . . ?
C13 N1 C19 124.02(19) . . ?
C11 N1 C13 111.27(17) . . ?
C11 N1 C19 123.89(19) . . ?
O1 C9 C1 122.4(2) . . ?
O1 C9 C8 122.84(18) . . ?
C8 C9 C1 114.72(18) . . ?
C12 C17 H17 120.2 . . ?
C12 C17 C16 119.6(2) . . ?
C16 C17 H17 120.2 . . ?
C6 C1 C9 119.7(2) . . ?
C6 C1 C2 118.57(19) . . ?
C2 C1 C9 121.7(2) . . ?
C17 C12 C13 120.33(19) . . ?
C17 C12 C10 130.69(19) . . ?
C13 C12 C10 108.93(17) . . ?
C12 C13 N1 109.62(18) . . ?
C14 C13 N1 128.6(2) . . ?
C14 C13 C12 121.8(2) . . ?
C9 C8 C10 117.79(18) . . ?
C7 C8 C9 120.10(18) . . ?
C7 C8 C10 122.1(2) . . ?
C17 C16 C18 119.3(2) . . ?
C15 C16 C17 118.5(2) . . ?
C15 C16 C18 122.1(2) . . ?
C12 C10 C8 113.89(17) . . ?
C12 C10 C11 101.12(16) . . ?
C12 C10 C20 110.64(17) . . ?
C8 C10 C11 109.53(16) . . ?
C8 C10 C20 113.88(18) . . ?
C20 C10 C11 106.78(16) . . ?
O4 C11 N1 125.6(2) . . ?
O4 C11 C10 125.5(2) . . ?
N1 C11 C10 108.77(17) . . ?
O2 C6 C1 122.06(18) . . ?
O2 C6 C5 116.3(2) . . ?
C1 C6 C5 121.7(2) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.6(2) . . ?
C3 C2 H2 120.2 . . ?
O3 C20 C10 110.08(17) . . ?
O3 C20 H20A 109.6 . . ?
O3 C20 H20B 109.6 . . ?
C10 C20 H20A 109.6 . . ?
C10 C20 H20B 109.6 . . ?
H20A C20 H20B 108.2 . . ?
O2 C7 H7 117.8 . . ?
C8 C7 O2 124.4(2) . . ?
C8 C7 H7 117.8 . . ?
C6 C5 H5 120.4 . . ?
C4 C5 C6 119.1(2) . . ?
C4 C5 H5 120.4 . . ?
C5 C4 H4 120.1 . . ?
C5 C4 C3 119.7(2) . . ?
C3 C4 H4 120.1 . . ?
C2 C3 Cl1 120.91(19) . . ?
C2 C3 C4 121.3(2) . . ?
C4 C3 Cl1 117.79(16) . . ?
C16 C15 H15 118.7 . . ?
C16 C15 C14 122.5(2) . . ?
C14 C15 H15 118.7 . . ?
C13 C14 C15 117.3(2) . . ?
C13 C14 H14 121.4 . . ?
C15 C14 H14 121.4 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.143
_oxdiff_exptl_absorpt_empirical_full_min 0.462
####################################################################### 
# 
# 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_my3
_database_code_depnum_ccdc_archive 'CCDC 1843639'
loop_
_audit_author_name
_audit_author_address
'Xiong-Li Liu'
;guizhou university
China
;
_audit_update_record             
;
2018-05-16 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;
_audit_creation_date             2017-11-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H14 Cl N O4'
_chemical_formula_sum            'C19 H14 Cl N O4'
_chemical_formula_weight         355.76
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   8.95357(19)
_cell_length_b                   11.3492(2)
_cell_length_c                   15.4615(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.458(2)
_cell_angle_gamma                90
_cell_volume                     1545.04(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4450
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.6510
_cell_measurement_theta_min      4.8770
_shelx_estimated_absorpt_T_max   0.760
_shelx_estimated_absorpt_T_min   0.670
_exptl_absorpt_coefficient_mu    2.420
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5451
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.860
_diffrn_reflns_theta_min         4.862
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     24.00  49.00   1.00    1.00    --   40.92-125.00-180.00   25
  2  ω     38.00 107.00   1.00    1.00    --  107.58 -94.00-120.00   69
  3  ω     39.00 132.00   1.00    1.00    --  107.58 -45.00-150.00   93
  4  ω     80.00 112.00   1.00    1.00    --  107.58  30.00 -30.00   32
  5  ω    124.00 176.00   1.00    1.00    --  107.58  45.00-120.00   52
  6  ω     94.00 178.00   1.00    1.00    --  107.58  45.00-180.00   84
  7  ω     37.00 115.00   1.00    1.00    --  107.58 -61.00  90.00   78
  8  ω   -104.00 -78.00   1.00    1.00    --  -40.92-144.00  21.00   26
  9  ω   -114.00 -17.00   1.00    1.00    --  -40.92 -37.00-120.00   97
 10  ω   -109.00 -47.00   1.00    1.00    --  -40.92 -37.00 -30.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0964289000
_diffrn_orient_matrix_UB_12      0.0413535000
_diffrn_orient_matrix_UB_13      -0.0672176000
_diffrn_orient_matrix_UB_21      -0.1215099000
_diffrn_orient_matrix_UB_22      -0.0475017000
_diffrn_orient_matrix_UB_23      -0.0754603000
_diffrn_orient_matrix_UB_31      -0.0807780000
_diffrn_orient_matrix_UB_32      0.1203992000
_diffrn_orient_matrix_UB_33      -0.0067665000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2915
_reflns_number_total             3018
_reflns_odcompleteness_completeness 99.62
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.626
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.0061(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3018
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.048
_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)+(0.0696P)²+1.0704P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.1165
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C13(H13), C14(H14), C7(H7), C2(H2), C5(H5), C4(H4), C3(H3A)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.66503(5) 0.13681(4) 0.23328(3) 0.02091(17) Uani 1 1 d . . . . .
O2 O 0.12843(14) 0.45817(11) 0.38430(8) 0.0167(3) Uani 1 1 d . . . . .
O4 O 0.23143(15) 0.69995(11) 0.11910(9) 0.0213(3) Uani 1 1 d . . . . .
O1 O 0.45026(14) 0.65879(11) 0.29794(8) 0.0189(3) Uani 1 1 d . . . . .
O3 O 0.01095(15) 0.50912(13) 0.10683(9) 0.0263(3) Uani 1 1 d . . . . .
H3 H 0.029114 0.578670 0.098750 0.039 Uiso 1 1 calc GR . . . .
N1 N 0.45288(16) 0.60461(13) 0.10409(9) 0.0142(3) Uani 1 1 d . . . . .
C17 C 0.42392(18) 0.42789(15) 0.17061(10) 0.0128(3) Uani 1 1 d . . . . .
C16 C 0.46425(19) 0.31613(15) 0.20103(11) 0.0138(3) Uani 1 1 d . . . . .
H16 H 0.399360 0.270246 0.227649 0.017 Uiso 1 1 calc R . . . .
C1 C 0.34024(19) 0.59273(14) 0.41803(11) 0.0136(3) Uani 1 1 d . . . . .
C13 C 0.6618(2) 0.45400(16) 0.11810(11) 0.0157(4) Uani 1 1 d . . . . .
H13 H 0.725838 0.499491 0.090595 0.019 Uiso 1 1 calc R . . . .
C8 C 0.25688(19) 0.51488(15) 0.26778(11) 0.0133(3) Uani 1 1 d . . . . .
C6 C 0.22792(19) 0.52366(15) 0.44407(11) 0.0138(3) Uani 1 1 d . . . . .
C9 C 0.35729(19) 0.59507(15) 0.32525(11) 0.0140(4) Uani 1 1 d . . . . .
C14 C 0.7041(2) 0.34114(16) 0.14984(11) 0.0169(4) Uani 1 1 d . . . . .
H14 H 0.798081 0.310652 0.143784 0.020 Uiso 1 1 calc R . . . .
C12 C 0.52091(19) 0.49552(15) 0.12915(10) 0.0135(3) Uani 1 1 d . . . . .
C10 C 0.28210(19) 0.49778(15) 0.17421(11) 0.0135(3) Uani 1 1 d . . . . .
C7 C 0.15038(19) 0.45379(15) 0.30036(11) 0.0155(4) Uani 1 1 d . . . . .
H7 H 0.086971 0.404681 0.261842 0.019 Uiso 1 1 calc R . . . .
C15 C 0.6066(2) 0.27455(15) 0.19027(11) 0.0151(4) Uani 1 1 d . . . . .
C2 C 0.4387(2) 0.65523(15) 0.48321(11) 0.0162(4) Uani 1 1 d . . . . .
H2 H 0.514647 0.702231 0.467568 0.019 Uiso 1 1 calc R . . . .
C18 C 0.5269(2) 0.70065(16) 0.06653(12) 0.0190(4) Uani 1 1 d . . . . .
H18A H 0.613413 0.726616 0.108238 0.029 Uiso 1 1 calc GR . . . .
H18B H 0.456823 0.764835 0.052518 0.029 Uiso 1 1 calc GR . . . .
H18C H 0.559369 0.674077 0.013981 0.029 Uiso 1 1 calc GR . . . .
C5 C 0.2112(2) 0.51447(16) 0.53169(12) 0.0167(4) Uani 1 1 d . . . . .
H5 H 0.135277 0.467642 0.547582 0.020 Uiso 1 1 calc R . . . .
C11 C 0.3173(2) 0.61545(15) 0.13170(11) 0.0149(4) Uani 1 1 d . . . . .
C4 C 0.3098(2) 0.57650(16) 0.59424(11) 0.0183(4) Uani 1 1 d . . . . .
H4 H 0.300765 0.571230 0.653090 0.022 Uiso 1 1 calc R . . . .
C3 C 0.4236(2) 0.64740(16) 0.57009(12) 0.0184(4) Uani 1 1 d . . . . .
H3A H 0.489117 0.689244 0.612806 0.022 Uiso 1 1 calc R . . . .
C19 C 0.1450(2) 0.44272(17) 0.11194(12) 0.0184(4) Uani 1 1 d . . . . .
H19A H 0.169368 0.435709 0.053539 0.022 Uiso 1 1 calc R . . . .
H19B H 0.127557 0.364007 0.132438 0.022 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C15 1.7417(18) . ?
O2 C6 1.379(2) . ?
O2 C7 1.348(2) . ?
O4 C11 1.222(2) . ?
O1 C9 1.234(2) . ?
O3 H3 0.8200 . ?
O3 C19 1.407(2) . ?
N1 C12 1.403(2) . ?
N1 C18 1.451(2) . ?
N1 C11 1.364(2) . ?
C17 C16 1.378(2) . ?
C17 C12 1.399(2) . ?
C17 C10 1.507(2) . ?
C16 H16 0.9300 . ?
C16 C15 1.397(2) . ?
C1 C6 1.391(2) . ?
C1 C9 1.470(2) . ?
C1 C2 1.405(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.399(3) . ?
C13 C12 1.386(2) . ?
C8 C9 1.461(2) . ?
C8 C10 1.517(2) . ?
C8 C7 1.348(2) . ?
C6 C5 1.394(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(3) . ?
C10 C11 1.546(2) . ?
C10 C19 1.548(2) . ?
C7 H7 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.377(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C5 H5 0.9300 . ?
C5 C4 1.379(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.401(3) . ?
C3 H3A 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?

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 O2 C6 118.40(13) . . ?
C19 O3 H3 109.5 . . ?
C12 N1 C18 124.53(14) . . ?
C11 N1 C12 111.08(14) . . ?
C11 N1 C18 123.70(15) . . ?
C16 C17 C12 121.03(15) . . ?
C16 C17 C10 129.97(15) . . ?
C12 C17 C10 109.00(15) . . ?
C17 C16 H16 121.4 . . ?
C17 C16 C15 117.29(15) . . ?
C15 C16 H16 121.4 . . ?
C6 C1 C9 120.07(15) . . ?
C6 C1 C2 118.01(16) . . ?
C2 C1 C9 121.87(15) . . ?
C14 C13 H13 121.2 . . ?
C12 C13 H13 121.2 . . ?
C12 C13 C14 117.56(16) . . ?
C9 C8 C10 118.55(14) . . ?
C7 C8 C9 119.46(16) . . ?
C7 C8 C10 121.90(15) . . ?
O2 C6 C1 121.53(15) . . ?
O2 C6 C5 116.15(15) . . ?
C1 C6 C5 122.31(16) . . ?
O1 C9 C1 122.72(15) . . ?
O1 C9 C8 122.40(16) . . ?
C8 C9 C1 114.88(15) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.29(16) . . ?
C15 C14 H14 119.9 . . ?
C17 C12 N1 109.65(15) . . ?
C13 C12 N1 128.70(16) . . ?
C13 C12 C17 121.65(16) . . ?
C17 C10 C8 112.02(13) . . ?
C17 C10 C11 101.60(13) . . ?
C17 C10 C19 110.06(14) . . ?
C8 C10 C11 111.85(14) . . ?
C8 C10 C19 113.98(14) . . ?
C11 C10 C19 106.50(14) . . ?
O2 C7 C8 125.25(16) . . ?
O2 C7 H7 117.4 . . ?
C8 C7 H7 117.4 . . ?
C16 C15 Cl1 118.36(13) . . ?
C14 C15 Cl1 119.43(13) . . ?
C14 C15 C16 122.17(16) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.48(16) . . ?
C3 C2 H2 119.8 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C6 C5 H5 120.8 . . ?
C4 C5 C6 118.37(16) . . ?
C4 C5 H5 120.8 . . ?
O4 C11 N1 126.20(16) . . ?
O4 C11 C10 125.10(16) . . ?
N1 C11 C10 108.47(14) . . ?
C5 C4 H4 119.6 . . ?
C5 C4 C3 120.71(16) . . ?
C3 C4 H4 119.6 . . ?
C2 C3 C4 120.12(17) . . ?
C2 C3 H3A 119.9 . . ?
C4 C3 H3A 119.9 . . ?
O3 C19 C10 113.01(15) . . ?
O3 C19 H19A 109.0 . . ?
O3 C19 H19B 109.0 . . ?
C10 C19 H19A 109.0 . . ?
C10 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C6 C5 C4 178.77(15) . . . . ?
C17 C16 C15 Cl1 176.62(12) . . . . ?
C17 C16 C15 C14 -0.8(2) . . . . ?
C17 C10 C11 O4 178.69(16) . . . . ?
C17 C10 C11 N1 3.96(17) . . . . ?
C17 C10 C19 O3 -175.28(14) . . . . ?
C16 C17 C12 N1 179.56(14) . . . . ?
C16 C17 C12 C13 -1.0(3) . . . . ?
C16 C17 C10 C8 58.3(2) . . . . ?
C16 C17 C10 C11 177.81(16) . . . . ?
C16 C17 C10 C19 -69.6(2) . . . . ?
C1 C6 C5 C4 0.1(3) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C13 C14 C15 Cl1 -177.36(13) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C8 C10 C11 O4 -61.7(2) . . . . ?
C8 C10 C11 N1 123.61(15) . . . . ?
C8 C10 C19 O3 57.9(2) . . . . ?
C6 O2 C7 C8 -4.6(3) . . . . ?
C6 C1 C9 O1 176.59(16) . . . . ?
C6 C1 C9 C8 -4.2(2) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
C6 C5 C4 C3 0.3(3) . . . . ?
C9 C1 C6 O2 -1.4(2) . . . . ?
C9 C1 C6 C5 177.21(15) . . . . ?
C9 C1 C2 C3 -177.31(16) . . . . ?
C9 C8 C10 C17 71.49(19) . . . . ?
C9 C8 C10 C11 -41.8(2) . . . . ?
C9 C8 C10 C19 -162.71(15) . . . . ?
C9 C8 C7 O2 -1.2(3) . . . . ?
C14 C13 C12 N1 179.53(15) . . . . ?
C14 C13 C12 C17 0.2(2) . . . . ?
C12 N1 C11 O4 -179.35(16) . . . . ?
C12 N1 C11 C10 -4.69(18) . . . . ?
C12 C17 C16 C15 1.2(2) . . . . ?
C12 C17 C10 C8 -121.44(15) . . . . ?
C12 C17 C10 C11 -1.91(17) . . . . ?
C12 C17 C10 C19 110.65(16) . . . . ?
C12 C13 C14 C15 0.3(2) . . . . ?
C10 C17 C16 C15 -178.46(16) . . . . ?
C10 C17 C12 N1 -0.69(19) . . . . ?
C10 C17 C12 C13 178.79(15) . . . . ?
C10 C8 C9 O1 8.2(2) . . . . ?
C10 C8 C9 C1 -171.06(14) . . . . ?
C10 C8 C7 O2 175.16(15) . . . . ?
C7 O2 C6 C1 5.9(2) . . . . ?
C7 O2 C6 C5 -172.83(15) . . . . ?
C7 C8 C9 O1 -175.30(16) . . . . ?
C7 C8 C9 C1 5.4(2) . . . . ?
C7 C8 C10 C17 -104.93(18) . . . . ?
C7 C8 C10 C11 141.75(17) . . . . ?
C7 C8 C10 C19 20.9(2) . . . . ?
C2 C1 C6 O2 -178.92(15) . . . . ?
C2 C1 C6 C5 -0.3(3) . . . . ?
C2 C1 C9 O1 -6.0(3) . . . . ?
C2 C1 C9 C8 173.28(15) . . . . ?
C18 N1 C12 C17 174.24(15) . . . . ?
C18 N1 C12 C13 -5.2(3) . . . . ?
C18 N1 C11 O4 9.8(3) . . . . ?
C18 N1 C11 C10 -175.54(15) . . . . ?
C5 C4 C3 C2 -0.4(3) . . . . ?
C11 N1 C12 C17 3.48(19) . . . . ?
C11 N1 C12 C13 -175.96(17) . . . . ?
C11 C10 C19 O3 -65.92(18) . . . . ?
C19 C10 C11 O4 63.5(2) . . . . ?
C19 C10 C11 N1 -111.25(15) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.700
_oxdiff_exptl_absorpt_empirical_full_min 0.667
####################################################################### 
# 
# 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_gy-h-7
_database_code_depnum_ccdc_archive 'CCDC 1919047'
loop_
_audit_author_name
_audit_author_address
'Xiong-Li Liu'
;guizhou university
China
;
_audit_update_record             
;
2019-05-28 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;
_audit_creation_date             2018-08-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H15 N O3'
_chemical_formula_sum            'C19 H15 N O3'
_chemical_formula_weight         305.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   10.7035(6)
_cell_length_b                   12.0971(6)
_cell_length_c                   11.5118(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.000(5)
_cell_angle_gamma                90
_cell_volume                     1490.34(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4673
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.3120
_cell_measurement_theta_min      3.1190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42396
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9426
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.983
_diffrn_reflns_theta_max         24.983
_diffrn_reflns_theta_min         2.442
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -55.00  39.00   1.00    1.50    --   11.90 -57.00 -90.00   94
  2  ω    -18.00  74.00   1.00    1.50    --   11.90  74.00-175.00   92
  3  ω    -10.00  83.00   1.00    1.50    --   11.90  57.00  60.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0563399000
_diffrn_orient_matrix_UB_12      -0.0242745000
_diffrn_orient_matrix_UB_13      -0.0190585000
_diffrn_orient_matrix_UB_21      0.0348112000
_diffrn_orient_matrix_UB_22      0.0416338000
_diffrn_orient_matrix_UB_23      0.0295209000
_diffrn_orient_matrix_UB_31      0.0024126000
_diffrn_orient_matrix_UB_32      -0.0333894000
_diffrn_orient_matrix_UB_33      0.0506398000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2271
_reflns_number_total             2624
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2624
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      1.021
_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)+(0.0529P)²+0.4223P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1022
_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
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C3(H3), C5(H5), C4(H4), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.79995(10) 0.50017(8) 0.42314(8) 0.0263(3) Uani 1 1 d . . . . .
O1 O 0.79138(10) 0.71369(8) 0.69837(8) 0.0261(3) Uani 1 1 d . . . . .
O3 O 0.90742(10) 0.88298(8) 0.49393(9) 0.0257(3) Uani 1 1 d . . . . .
N1 N 0.73642(12) 0.95853(10) 0.58267(10) 0.0221(3) Uani 1 1 d . . . . .
C1 C 0.84760(13) 0.53678(12) 0.62595(12) 0.0190(3) Uani 1 1 d . . . . .
C8 C 0.74892(13) 0.67813(12) 0.49984(12) 0.0201(3) Uani 1 1 d . . . . .
C6 C 0.84726(14) 0.46672(12) 0.52985(12) 0.0214(3) Uani 1 1 d . . . . .
C2 C 0.90043(14) 0.49744(12) 0.73008(13) 0.0220(3) Uani 1 1 d . . . . .
H2 H 0.901921 0.542681 0.795404 0.026 Uiso 1 1 calc R . . . .
C17 C 0.79686(14) 0.88088(12) 0.51818(12) 0.0203(3) Uani 1 1 d . . . . .
C9 C 0.79484(13) 0.64863(12) 0.61576(12) 0.0198(3) Uani 1 1 d . . . . .
C16 C 0.61077(14) 0.92619(12) 0.60236(12) 0.0223(3) Uani 1 1 d . . . . .
C10 C 0.70197(14) 0.79371(12) 0.47912(12) 0.0218(3) Uani 1 1 d . . . . .
H10 H 0.685592 0.803023 0.395668 0.026 Uiso 1 1 calc R . . . .
C11 C 0.58667(14) 0.82773(12) 0.54343(12) 0.0227(3) Uani 1 1 d . . . . .
C7 C 0.75591(15) 0.60477(12) 0.41263(13) 0.0243(4) Uani 1 1 d . . . . .
H7 H 0.728392 0.627519 0.339381 0.029 Uiso 1 1 calc R . . . .
C3 C 0.95017(14) 0.39273(12) 0.73706(14) 0.0261(4) Uani 1 1 d . . . . .
H3 H 0.984867 0.367528 0.806791 0.031 Uiso 1 1 calc R . . . .
C5 C 0.89745(15) 0.36063(12) 0.53568(14) 0.0262(4) Uani 1 1 d . . . . .
H5 H 0.896429 0.315149 0.470538 0.031 Uiso 1 1 calc R . . . .
C4 C 0.94849(14) 0.32415(12) 0.63903(14) 0.0267(4) Uani 1 1 d . . . . .
H4 H 0.982165 0.253402 0.643964 0.032 Uiso 1 1 calc R . . . .
C15 C 0.52086(15) 0.97719(13) 0.67070(13) 0.0286(4) Uani 1 1 d . . . . .
C12 C 0.47213(15) 0.77697(14) 0.54881(14) 0.0289(4) Uani 1 1 d . . . . .
H12 H 0.456362 0.711503 0.508822 0.035 Uiso 1 1 calc R . . . .
C19 C 0.80014(15) 1.05911(13) 0.61975(13) 0.0269(4) Uani 1 1 d . . . . .
H19A H 0.813453 1.057387 0.702419 0.040 Uiso 1 1 calc GR . . . .
H19B H 0.749805 1.122079 0.599296 0.040 Uiso 1 1 calc GR . . . .
H19C H 0.879205 1.064210 0.582007 0.040 Uiso 1 1 calc GR . . . .
C13 C 0.38005(15) 0.82615(15) 0.61581(15) 0.0351(4) Uani 1 1 d . . . . .
H13 H 0.301554 0.793705 0.620769 0.042 Uiso 1 1 calc R . . . .
C14 C 0.40577(16) 0.92290(15) 0.67457(15) 0.0347(4) Uani 1 1 d . . . . .
H14 H 0.343159 0.953765 0.719239 0.042 Uiso 1 1 calc R . . . .
C18 C 0.53950(17) 1.08216(15) 0.73963(15) 0.0368(4) Uani 1 1 d . . . . .
H18A H 0.609767 1.073609 0.791820 0.055 Uiso 1 1 calc GR . . . .
H18B H 0.465882 1.097214 0.783382 0.055 Uiso 1 1 calc GR . . . .
H18C H 0.554708 1.142463 0.687535 0.055 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
O2 C6 1.3811(18) . ?
O2 C7 1.3551(18) . ?
O1 C9 1.2355(17) . ?
O3 C17 1.2209(18) . ?
N1 C17 1.3671(18) . ?
N1 C16 1.4226(19) . ?
N1 C19 1.4552(19) . ?
C1 C6 1.394(2) . ?
C1 C2 1.400(2) . ?
C1 C9 1.470(2) . ?
C8 C9 1.458(2) . ?
C8 C10 1.503(2) . ?
C8 C7 1.343(2) . ?
C6 C5 1.392(2) . ?
C2 C3 1.376(2) . ?
C17 C10 1.526(2) . ?
C16 C11 1.393(2) . ?
C16 C15 1.397(2) . ?
C10 C11 1.507(2) . ?
C11 C12 1.373(2) . ?
C3 C4 1.400(2) . ?
C5 C4 1.373(2) . ?
C15 C14 1.397(2) . ?
C15 C18 1.509(2) . ?
C12 C13 1.395(2) . ?
C13 C14 1.377(3) . ?

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 O2 C6 118.33(11) . . ?
C17 N1 C16 110.81(12) . . ?
C17 N1 C19 120.67(12) . . ?
C16 N1 C19 128.52(12) . . ?
C6 C1 C2 117.93(13) . . ?
C6 C1 C9 120.05(13) . . ?
C2 C1 C9 122.01(13) . . ?
C9 C8 C10 118.63(12) . . ?
C7 C8 C9 120.00(13) . . ?
C7 C8 C10 121.25(13) . . ?
O2 C6 C1 121.58(13) . . ?
O2 C6 C5 116.62(13) . . ?
C1 C6 C5 121.78(14) . . ?
C3 C2 C1 120.88(14) . . ?
O3 C17 N1 125.42(14) . . ?
O3 C17 C10 126.13(13) . . ?
N1 C17 C10 108.42(12) . . ?
O1 C9 C1 122.79(13) . . ?
O1 C9 C8 122.30(13) . . ?
C8 C9 C1 114.90(12) . . ?
C11 C16 N1 108.98(12) . . ?
C11 C16 C15 121.90(14) . . ?
C15 C16 N1 129.10(15) . . ?
C8 C10 C17 112.14(12) . . ?
C8 C10 C11 116.76(12) . . ?
C11 C10 C17 102.30(12) . . ?
C16 C11 C10 109.05(13) . . ?
C12 C11 C16 121.22(14) . . ?
C12 C11 C10 129.73(14) . . ?
C8 C7 O2 125.04(14) . . ?
C2 C3 C4 119.92(15) . . ?
C4 C5 C6 119.03(14) . . ?
C5 C4 C3 120.46(14) . . ?
C16 C15 C18 125.57(15) . . ?
C14 C15 C16 115.26(15) . . ?
C14 C15 C18 119.17(14) . . ?
C11 C12 C13 118.29(16) . . ?
C14 C13 C12 119.79(16) . . ?
C13 C14 C15 123.54(15) . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.722
_oxdiff_exptl_absorpt_empirical_full_min 0.732
####################################################################### 
# 
# 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_lyl01
_database_code_depnum_ccdc_archive 'CCDC 1843641'
loop_
_audit_author_name
_audit_author_address
'Xiong-Li Liu'
;guizhou university
China
;
_audit_update_record             
;
2018-05-16 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;
_audit_creation_date             2017-11-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H14 F N O4'
_chemical_formula_sum            'C19 H14 F N O4'
_chemical_formula_weight         339.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.8536(3)
_cell_length_b                   11.0840(4)
_cell_length_c                   15.3754(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.430(4)
_cell_angle_gamma                90
_cell_volume                     1478.91(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5281
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.3370
_cell_measurement_theta_min      3.9010
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12618
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.536
_diffrn_reflns_theta_min         3.461
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -32.00  38.00   1.00    2.00    --   11.74 -57.00  60.00   70
  2  ω     -6.00  27.00   1.00    2.00    --  -11.59 -99.00 -60.00   33
  3  ω     -4.00  73.00   1.00    2.00    --   11.74  77.00 -90.00   77
  4  ω     -2.00  86.00   1.00    2.00    --   11.74  37.00-150.00   88
  5  ω     44.00  70.00   1.00    2.00    --   11.74 178.00  60.00   26
  6  ω    -65.00 -27.00   1.00    2.00    --   11.74 -19.00  30.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0007942000
_diffrn_orient_matrix_UB_12      -0.0235841000
_diffrn_orient_matrix_UB_13      0.0427911000
_diffrn_orient_matrix_UB_21      0.0817194000
_diffrn_orient_matrix_UB_22      0.0013127000
_diffrn_orient_matrix_UB_23      0.0101533000
_diffrn_orient_matrix_UB_31      -0.0020806000
_diffrn_orient_matrix_UB_32      0.0594658000
_diffrn_orient_matrix_UB_33      0.0167452000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3048
_reflns_number_total             3609
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3609
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0437
_refine_ls_restrained_S_all      1.040
_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)+(0.0508P)²+0.7345P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1131
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C18(H18), C9(H9), C3(H3), C15(H15), C2(H2), C4(H4A), C16(H16)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.63381(11) 0.86973(8) 0.21998(6) 0.0261(2) Uani 1 1 d . . . . .
O1 O 0.12389(12) 0.54649(9) 0.38494(6) 0.0178(2) Uani 1 1 d . . . . .
O2 O 0.46082(12) 0.35057(9) 0.30357(6) 0.0189(2) Uani 1 1 d . . . . .
O3 O 0.24836(12) 0.30451(9) 0.12162(7) 0.0207(2) Uani 1 1 d . . . . .
O4 O 0.01313(12) 0.48555(11) 0.10587(7) 0.0249(3) Uani 1 1 d . . . . .
H4 H 0.038732 0.415314 0.100308 0.037 Uiso 1 1 calc GR . . . .
N1 N 0.46959(14) 0.40964(11) 0.11164(8) 0.0164(3) Uani 1 1 d . . . . .
C8 C 0.25907(16) 0.49391(12) 0.27038(9) 0.0143(3) Uani 1 1 d . . . . .
C14 C 0.53073(16) 0.52443(13) 0.13697(9) 0.0158(3) Uani 1 1 d . . . . .
C1 C 0.22547(16) 0.48043(13) 0.44594(9) 0.0154(3) Uani 1 1 d . . . . .
C12 C 0.42537(16) 0.59042(13) 0.17440(9) 0.0143(3) Uani 1 1 d . . . . .
C13 C 0.33066(16) 0.39381(13) 0.13602(9) 0.0161(3) Uani 1 1 d . . . . .
C7 C 0.36247(16) 0.41271(12) 0.32908(9) 0.0142(3) Uani 1 1 d . . . . .
C5 C 0.44047(17) 0.34678(13) 0.48796(9) 0.0169(3) Uani 1 1 d . . . . .
H5 H 0.518398 0.299481 0.473160 0.020 Uiso 1 1 calc R . . . .
C6 C 0.34110(16) 0.41155(12) 0.42153(9) 0.0147(3) Uani 1 1 d . . . . .
C18 C 0.45771(16) 0.70782(13) 0.20255(9) 0.0163(3) Uani 1 1 d . . . . .
H18 H 0.388543 0.753214 0.227269 0.020 Uiso 1 1 calc R . . . .
C9 C 0.14761(16) 0.55270(13) 0.30095(9) 0.0169(3) Uani 1 1 d . . . . .
H9 H 0.081650 0.601455 0.261216 0.020 Uiso 1 1 calc R . . . .
C17 C 0.59845(17) 0.75451(13) 0.19211(9) 0.0194(3) Uani 1 1 d . . . . .
C3 C 0.30689(17) 0.42509(14) 0.59782(9) 0.0196(3) Uani 1 1 d . . . . .
H3 H 0.296965 0.429867 0.656813 0.023 Uiso 1 1 calc R . . . .
C15 C 0.67197(17) 0.57179(14) 0.12810(10) 0.0192(3) Uani 1 1 d . . . . .
H15 H 0.741958 0.526333 0.104086 0.023 Uiso 1 1 calc R . . . .
C11 C 0.14317(16) 0.56146(14) 0.11190(9) 0.0182(3) Uani 1 1 d . . . . .
H11A H 0.118108 0.640808 0.131572 0.022 Uiso 1 1 calc R . . . .
H11B H 0.167587 0.570132 0.053437 0.022 Uiso 1 1 calc R . . . .
C2 C 0.20736(17) 0.48887(13) 0.53398(9) 0.0186(3) Uani 1 1 d . . . . .
H2 H 0.129940 0.536431 0.549100 0.022 Uiso 1 1 calc R . . . .
C4 C 0.42290(17) 0.35309(13) 0.57476(9) 0.0187(3) Uani 1 1 d . . . . .
H4A H 0.488315 0.309372 0.618311 0.022 Uiso 1 1 calc R . . . .
C16 C 0.70518(17) 0.69033(14) 0.15658(10) 0.0208(3) Uani 1 1 d . . . . .
H16 H 0.798407 0.725603 0.151613 0.025 Uiso 1 1 calc R . . . .
C10 C 0.28608(16) 0.51260(12) 0.17651(9) 0.0143(3) Uani 1 1 d . . . . .
C19 C 0.55453(18) 0.31353(14) 0.07895(10) 0.0218(3) Uani 1 1 d . . . . .
H19A H 0.585630 0.339394 0.025553 0.033 Uiso 1 1 calc GR . . . .
H19B H 0.490050 0.243484 0.066658 0.033 Uiso 1 1 calc GR . . . .
H19C H 0.644141 0.294077 0.122993 0.033 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 C17 1.3636(17) . ?
O1 C1 1.3749(17) . ?
O1 C9 1.3505(16) . ?
O2 C7 1.2336(17) . ?
O3 C13 1.2230(18) . ?
O4 H4 0.8200 . ?
O4 C11 1.4142(18) . ?
N1 C14 1.4071(18) . ?
N1 C13 1.3664(18) . ?
N1 C19 1.4501(18) . ?
C8 C7 1.4612(19) . ?
C8 C9 1.343(2) . ?
C8 C10 1.5231(18) . ?
C14 C12 1.396(2) . ?
C14 C15 1.388(2) . ?
C1 C6 1.387(2) . ?
C1 C2 1.3973(19) . ?
C12 C18 1.383(2) . ?
C12 C10 1.5105(19) . ?
C13 C10 1.5409(19) . ?
C7 C6 1.4707(18) . ?
C5 H5 0.9300 . ?
C5 C6 1.406(2) . ?
C5 C4 1.376(2) . ?
C18 H18 0.9300 . ?
C18 C17 1.388(2) . ?
C9 H9 0.9300 . ?
C17 C16 1.379(2) . ?
C3 H3 0.9300 . ?
C3 C2 1.377(2) . ?
C3 C4 1.401(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.398(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C10 1.5437(19) . ?
C2 H2 0.9300 . ?
C4 H4A 0.9300 . ?
C16 H16 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C1 118.35(11) . . ?
C11 O4 H4 109.5 . . ?
C14 N1 C19 124.24(12) . . ?
C13 N1 C14 110.98(11) . . ?
C13 N1 C19 123.89(12) . . ?
C7 C8 C10 118.18(12) . . ?
C9 C8 C7 119.78(12) . . ?
C9 C8 C10 122.00(12) . . ?
C12 C14 N1 109.63(12) . . ?
C15 C14 N1 128.29(13) . . ?
C15 C14 C12 122.07(14) . . ?
O1 C1 C6 121.77(12) . . ?
O1 C1 C2 116.11(12) . . ?
C6 C1 C2 122.11(13) . . ?
C14 C12 C10 108.95(12) . . ?
C18 C12 C14 120.53(13) . . ?
C18 C12 C10 130.52(13) . . ?
O3 C13 N1 126.20(13) . . ?
O3 C13 C10 125.00(13) . . ?
N1 C13 C10 108.53(12) . . ?
O2 C7 C8 122.88(12) . . ?
O2 C7 C6 122.44(12) . . ?
C8 C7 C6 114.68(12) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.27(14) . . ?
C1 C6 C7 120.00(12) . . ?
C1 C6 C5 118.27(13) . . ?
C5 C6 C7 121.66(13) . . ?
C12 C18 H18 121.6 . . ?
C12 C18 C17 116.72(13) . . ?
C17 C18 H18 121.6 . . ?
O1 C9 H9 117.5 . . ?
C8 C9 O1 125.05(13) . . ?
C8 C9 H9 117.5 . . ?
F1 C17 C18 117.93(13) . . ?
F1 C17 C16 118.36(13) . . ?
C16 C17 C18 123.70(14) . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.65(13) . . ?
C4 C3 H3 119.7 . . ?
C14 C15 H15 121.2 . . ?
C14 C15 C16 117.56(14) . . ?
C16 C15 H15 121.2 . . ?
O4 C11 H11A 109.0 . . ?
O4 C11 H11B 109.0 . . ?
O4 C11 C10 112.72(12) . . ?
H11A C11 H11B 107.8 . . ?
C10 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.42(13) . . ?
C3 C2 H2 120.8 . . ?
C5 C4 C3 120.27(14) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C17 C16 C15 119.40(14) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C8 C10 C13 111.56(11) . . ?
C8 C10 C11 113.26(11) . . ?
C12 C10 C8 112.35(11) . . ?
C12 C10 C13 101.75(11) . . ?
C12 C10 C11 110.75(11) . . ?
C13 C10 C11 106.42(11) . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.234
_oxdiff_exptl_absorpt_empirical_full_min 0.768
####################################################################### 
# 
# 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_my-13
_database_code_depnum_ccdc_archive 'CCDC 1843642'
loop_
_audit_author_name
_audit_author_address
'Xiong-Li Liu'
;guizhou university
China
;
_audit_update_record             
;
2018-05-16 deposited with the CCDC.	2019-11-04 downloaded from the CCDC.
;
_audit_creation_date             2017-11-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H18 F N O4'
_chemical_formula_sum            'C25 H18 F N O4'
_chemical_formula_weight         415.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.5670(8)
_cell_length_b                   21.4436(16)
_cell_length_c                   9.5202(9)
_cell_angle_alpha                90
_cell_angle_beta                 114.050(10)
_cell_angle_gamma                90
_cell_volume                     1970.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3132
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.1530
_cell_measurement_theta_min      4.0180
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.840
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10494
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.840
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.524
_diffrn_reflns_theta_min         3.547
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.840
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      2.00  29.00   1.00    2.00    --  -11.59 -99.00-120.00   27
  2  ω      7.00  84.00   1.00    2.00    --   11.74  37.00-180.00   77
  3  ω    -16.00  84.00   1.00    2.00    --   11.74  57.00 -90.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0288822000
_diffrn_orient_matrix_UB_12      -0.0274491000
_diffrn_orient_matrix_UB_13      0.0426993000
_diffrn_orient_matrix_UB_21      -0.0435817000
_diffrn_orient_matrix_UB_22      -0.0184794000
_diffrn_orient_matrix_UB_23      -0.0629111000
_diffrn_orient_matrix_UB_31      0.0516922000
_diffrn_orient_matrix_UB_32      -0.0002312000
_diffrn_orient_matrix_UB_33      -0.0295312000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3267
_reflns_number_total             4629
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4629
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0557
_refine_ls_restrained_S_all      1.032
_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)+(0.0437P)²+0.2916P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1241
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C16(H16), C8(H8), C6(H6), C14(H14), C3(H3), C4(H4A), C5(H5),
 C24(H24), C20(H20), C21(H21), C23(H23), C22(H22)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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 0.60547(10) 0.53044(6) 0.12115(13) 0.0305(3) Uani 1 1 d . . . . .
O2 O 0.55865(12) 0.81203(6) 0.43320(14) 0.0224(3) Uani 1 1 d . . . . .
O3 O 0.21320(12) 0.67038(6) 0.49250(14) 0.0217(3) Uani 1 1 d . . . . .
O1 O 0.54646(12) 0.64032(7) 0.60782(14) 0.0247(3) Uani 1 1 d . . . . .
O4 O 0.26757(13) 0.70766(7) 0.06218(15) 0.0257(3) Uani 1 1 d . . . . .
H4 H 0.251987 0.744276 0.035980 0.039 Uiso 1 1 calc GR . . . .
N1 N 0.25877(13) 0.57712(7) 0.40452(16) 0.0174(3) Uani 1 1 d . . . . .
C12 C 0.33968(16) 0.55649(9) 0.32591(19) 0.0169(4) Uani 1 1 d . . . . .
C7 C 0.66662(16) 0.79318(9) 0.5660(2) 0.0201(4) Uani 1 1 d . . . . .
C11 C 0.39000(16) 0.60779(9) 0.2770(2) 0.0176(4) Uani 1 1 d . . . . .
C2 C 0.66888(17) 0.73472(9) 0.6285(2) 0.0203(4) Uani 1 1 d . . . . .
C1 C 0.55460(17) 0.69129(9) 0.5527(2) 0.0190(4) Uani 1 1 d . . . . .
C17 C 0.26439(16) 0.63967(9) 0.4196(2) 0.0179(4) Uani 1 1 d . . . . .
C10 C 0.33558(16) 0.66666(9) 0.31950(19) 0.0177(4) Uani 1 1 d . . . . .
C9 C 0.44856(16) 0.71260(9) 0.4067(2) 0.0175(4) Uani 1 1 d . . . . .
C13 C 0.37241(16) 0.49615(9) 0.3041(2) 0.0194(4) Uani 1 1 d . . . . .
H13 H 0.336523 0.462293 0.336877 0.023 Uiso 1 1 calc R . . . .
C16 C 0.47918(17) 0.59995(9) 0.2050(2) 0.0210(4) Uani 1 1 d . . . . .
H16 H 0.514507 0.633758 0.171315 0.025 Uiso 1 1 calc R . . . .
C15 C 0.51297(17) 0.53935(10) 0.1856(2) 0.0224(4) Uani 1 1 d . . . . .
C8 C 0.45595(17) 0.77077(9) 0.3589(2) 0.0204(4) Uani 1 1 d . . . . .
H8 H 0.385027 0.783800 0.267517 0.024 Uiso 1 1 calc R . . . .
C18 C 0.19801(17) 0.53518(9) 0.4805(2) 0.0204(4) Uani 1 1 d . . . . .
H18A H 0.153018 0.559781 0.532507 0.025 Uiso 1 1 calc R . . . .
H18B H 0.271491 0.511383 0.558052 0.025 Uiso 1 1 calc R . . . .
C19 C 0.09379(17) 0.49061(9) 0.3713(2) 0.0197(4) Uani 1 1 d . . . . .
C6 C 0.77189(17) 0.83668(10) 0.6349(2) 0.0261(5) Uani 1 1 d . . . . .
H6 H 0.768109 0.875886 0.591597 0.031 Uiso 1 1 calc R . . . .
C14 C 0.46186(17) 0.48793(10) 0.2305(2) 0.0224(4) Uani 1 1 d . . . . .
H14 H 0.486374 0.448057 0.212252 0.027 Uiso 1 1 calc R . . . .
C25 C 0.21809(18) 0.69453(9) 0.1762(2) 0.0210(4) Uani 1 1 d . . . . .
H25A H 0.141743 0.665210 0.136186 0.025 Uiso 1 1 calc R . . . .
H25B H 0.184256 0.732554 0.204143 0.025 Uiso 1 1 calc R . . . .
C3 C 0.78209(18) 0.71916(10) 0.7650(2) 0.0263(5) Uani 1 1 d . . . . .
H3 H 0.786105 0.680188 0.809489 0.032 Uiso 1 1 calc R . . . .
C4 C 0.88733(19) 0.76150(11) 0.8333(2) 0.0315(5) Uani 1 1 d . . . . .
H4A H 0.962769 0.750821 0.923315 0.038 Uiso 1 1 calc R . . . .
C5 C 0.88154(18) 0.81996(11) 0.7688(2) 0.0290(5) Uani 1 1 d . . . . .
H5 H 0.952840 0.848289 0.816793 0.035 Uiso 1 1 calc R . . . .
C24 C -0.00402(18) 0.50984(11) 0.2297(2) 0.0292(5) Uani 1 1 d . . . . .
H24 H -0.004161 0.550977 0.198718 0.035 Uiso 1 1 calc R . . . .
C20 C 0.09455(19) 0.42900(10) 0.4137(2) 0.0275(5) Uani 1 1 d . . . . .
H20 H 0.161021 0.415247 0.507338 0.033 Uiso 1 1 calc R . . . .
C21 C -0.0032(2) 0.38737(11) 0.3176(3) 0.0374(6) Uani 1 1 d . . . . .
H21 H -0.002279 0.346054 0.347615 0.045 Uiso 1 1 calc R . . . .
C23 C -0.1016(2) 0.46838(12) 0.1339(3) 0.0390(6) Uani 1 1 d . . . . .
H23 H -0.167457 0.481884 0.039604 0.047 Uiso 1 1 calc R . . . .
C22 C -0.1011(2) 0.40701(12) 0.1782(3) 0.0408(6) Uani 1 1 d . . . . .
H22 H -0.166726 0.379147 0.114141 0.049 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 C15 1.3630(19) . ?
O2 C7 1.374(2) . ?
O2 C8 1.355(2) . ?
O3 C17 1.230(2) . ?
O1 C1 1.231(2) . ?
O4 H4 0.8200 . ?
O4 C25 1.412(2) . ?
N1 C12 1.417(2) . ?
N1 C17 1.348(2) . ?
N1 C18 1.457(2) . ?
C12 C11 1.382(3) . ?
C12 C13 1.377(3) . ?
C7 C2 1.384(3) . ?
C7 C6 1.394(3) . ?
C11 C10 1.509(3) . ?
C11 C16 1.384(2) . ?
C2 C1 1.462(2) . ?
C2 C3 1.401(2) . ?
C1 C9 1.458(2) . ?
C17 C10 1.547(2) . ?
C10 C9 1.509(2) . ?
C10 C25 1.543(2) . ?
C9 C8 1.341(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.398(2) . ?
C16 H16 0.9300 . ?
C16 C15 1.380(3) . ?
C15 C14 1.371(3) . ?
C8 H8 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.508(2) . ?
C19 C24 1.386(3) . ?
C19 C20 1.380(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.376(3) . ?
C14 H14 0.9300 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C3 H3 0.9300 . ?
C3 C4 1.376(3) . ?
C4 H4A 0.9300 . ?
C4 C5 1.386(3) . ?
C5 H5 0.9300 . ?
C24 H24 0.9300 . ?
C24 C23 1.385(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.389(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.375(3) . ?
C23 H23 0.9300 . ?
C23 C22 1.381(3) . ?
C22 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O2 C7 118.45(15) . . ?
C25 O4 H4 109.5 . . ?
C12 N1 C18 123.53(16) . . ?
C17 N1 C12 110.93(14) . . ?
C17 N1 C18 124.78(15) . . ?
C11 C12 N1 109.08(16) . . ?
C13 C12 N1 128.01(16) . . ?
C13 C12 C11 122.85(16) . . ?
O2 C7 C2 121.66(16) . . ?
O2 C7 C6 116.13(17) . . ?
C2 C7 C6 122.21(17) . . ?
C12 C11 C10 109.55(15) . . ?
C12 C11 C16 120.22(17) . . ?
C16 C11 C10 130.21(17) . . ?
C7 C2 C1 119.90(16) . . ?
C7 C2 C3 118.25(17) . . ?
C3 C2 C1 121.85(18) . . ?
O1 C1 C2 122.84(16) . . ?
O1 C1 C9 121.65(16) . . ?
C9 C1 C2 115.50(17) . . ?
O3 C17 N1 125.63(17) . . ?
O3 C17 C10 125.68(18) . . ?
N1 C17 C10 108.53(15) . . ?
C11 C10 C17 100.74(15) . . ?
C11 C10 C9 113.02(13) . . ?
C11 C10 C25 110.15(14) . . ?
C9 C10 C17 112.29(14) . . ?
C9 C10 C25 113.87(15) . . ?
C25 C10 C17 105.77(13) . . ?
C1 C9 C10 116.62(16) . . ?
C8 C9 C1 119.12(16) . . ?
C8 C9 C10 124.25(16) . . ?
C12 C13 H13 121.4 . . ?
C12 C13 C14 117.18(17) . . ?
C14 C13 H13 121.4 . . ?
C11 C16 H16 121.7 . . ?
C15 C16 C11 116.50(17) . . ?
C15 C16 H16 121.7 . . ?
F1 C15 C16 117.66(17) . . ?
F1 C15 C14 118.27(17) . . ?
C14 C15 C16 124.05(17) . . ?
O2 C8 H8 117.4 . . ?
C9 C8 O2 125.11(16) . . ?
C9 C8 H8 117.4 . . ?
N1 C18 H18A 108.9 . . ?
N1 C18 H18B 108.9 . . ?
N1 C18 C19 113.24(14) . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
C24 C19 C18 121.85(18) . . ?
C20 C19 C18 119.31(16) . . ?
C20 C19 C24 118.83(18) . . ?
C7 C6 H6 121.0 . . ?
C5 C6 C7 118.1(2) . . ?
C5 C6 H6 121.0 . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.17(18) . . ?
C15 C14 H14 120.4 . . ?
O4 C25 C10 109.91(14) . . ?
O4 C25 H25A 109.7 . . ?
O4 C25 H25B 109.7 . . ?
C10 C25 H25A 109.7 . . ?
C10 C25 H25B 109.7 . . ?
H25A C25 H25B 108.2 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4A 119.8 . . ?
C3 C4 C5 120.38(18) . . ?
C5 C4 H4A 119.8 . . ?
C6 C5 C4 120.99(19) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C19 C24 H24 119.7 . . ?
C23 C24 C19 120.6(2) . . ?
C23 C24 H24 119.7 . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.5(2) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.3(2) . . ?
C22 C21 H21 119.9 . . ?
C24 C23 H23 120.0 . . ?
C22 C23 C24 120.1(2) . . ?
C22 C23 H23 120.0 . . ?
C21 C22 C23 119.6(2) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?

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
F1 C15 C14 C13 176.73(15) . . . . ?
O2 C7 C2 C1 0.2(3) . . . . ?
O2 C7 C2 C3 -179.42(16) . . . . ?
O2 C7 C6 C5 179.46(16) . . . . ?
O3 C17 C10 C11 173.76(16) . . . . ?
O3 C17 C10 C9 53.2(2) . . . . ?
O3 C17 C10 C25 -71.5(2) . . . . ?
O1 C1 C9 C10 -5.6(2) . . . . ?
O1 C1 C9 C8 173.93(16) . . . . ?
N1 C12 C11 C10 -2.32(18) . . . . ?
N1 C12 C11 C16 176.14(15) . . . . ?
N1 C12 C13 C14 -175.99(15) . . . . ?
N1 C17 C10 C11 -10.72(17) . . . . ?
N1 C17 C10 C9 -131.25(15) . . . . ?
N1 C17 C10 C25 103.97(16) . . . . ?
N1 C18 C19 C24 -43.1(2) . . . . ?
N1 C18 C19 C20 137.56(17) . . . . ?
C12 N1 C17 O3 -174.27(15) . . . . ?
C12 N1 C17 C10 10.21(18) . . . . ?
C12 N1 C18 C19 -62.7(2) . . . . ?
C12 C11 C10 C17 7.66(17) . . . . ?
C12 C11 C10 C9 127.67(15) . . . . ?
C12 C11 C10 C25 -103.70(16) . . . . ?
C12 C11 C16 C15 0.1(2) . . . . ?
C12 C13 C14 C15 0.6(2) . . . . ?
C7 O2 C8 C9 1.9(2) . . . . ?
C7 C2 C1 O1 -175.25(17) . . . . ?
C7 C2 C1 C9 4.0(2) . . . . ?
C7 C2 C3 C4 0.0(3) . . . . ?
C7 C6 C5 C4 0.1(3) . . . . ?
C11 C12 C13 C14 0.7(2) . . . . ?
C11 C10 C9 C1 -60.0(2) . . . . ?
C11 C10 C9 C8 120.45(19) . . . . ?
C11 C10 C25 O4 -58.78(19) . . . . ?
C11 C16 C15 F1 -177.13(14) . . . . ?
C11 C16 C15 C14 1.2(3) . . . . ?
C2 C7 C6 C5 0.6(3) . . . . ?
C2 C1 C9 C10 175.12(14) . . . . ?
C2 C1 C9 C8 -5.3(2) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C1 C2 C3 C4 -179.68(17) . . . . ?
C1 C9 C8 O2 2.6(3) . . . . ?
C17 N1 C12 C11 -5.18(19) . . . . ?
C17 N1 C12 C13 171.92(16) . . . . ?
C17 N1 C18 C19 128.26(17) . . . . ?
C17 C10 C9 C1 53.1(2) . . . . ?
C17 C10 C9 C8 -126.40(18) . . . . ?
C17 C10 C25 O4 -166.83(15) . . . . ?
C10 C11 C16 C15 178.24(16) . . . . ?
C10 C9 C8 O2 -177.94(15) . . . . ?
C9 C10 C25 O4 69.38(19) . . . . ?
C13 C12 C11 C10 -179.59(15) . . . . ?
C13 C12 C11 C16 -1.1(3) . . . . ?
C16 C11 C10 C17 -170.60(17) . . . . ?
C16 C11 C10 C9 -50.6(2) . . . . ?
C16 C11 C10 C25 78.0(2) . . . . ?
C16 C15 C14 C13 -1.6(3) . . . . ?
C8 O2 C7 C2 -3.3(2) . . . . ?
C8 O2 C7 C6 177.82(15) . . . . ?
C18 N1 C12 C11 -175.57(14) . . . . ?
C18 N1 C12 C13 1.5(3) . . . . ?
C18 N1 C17 O3 -4.0(3) . . . . ?
C18 N1 C17 C10 -179.54(14) . . . . ?
C18 C19 C24 C23 -177.77(17) . . . . ?
C18 C19 C20 C21 177.86(16) . . . . ?
C19 C24 C23 C22 -0.8(3) . . . . ?
C19 C20 C21 C22 0.6(3) . . . . ?
C6 C7 C2 C1 179.02(16) . . . . ?
C6 C7 C2 C3 -0.6(3) . . . . ?
C25 C10 C9 C1 173.29(15) . . . . ?
C25 C10 C9 C8 -6.2(2) . . . . ?
C3 C2 C1 O1 4.4(3) . . . . ?
C3 C2 C1 C9 -176.35(16) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C24 C19 C20 C21 -1.5(3) . . . . ?
C24 C23 C22 C21 -0.2(3) . . . . ?
C20 C19 C24 C23 1.6(3) . . . . ?
C20 C21 C22 C23 0.3(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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.468
_oxdiff_exptl_absorpt_empirical_full_min 0.608
