# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_16-1-02
_database_code_depnum_ccdc_archive 'CCDC 1993371'
loop_
_audit_author_name
_audit_author_address
'Xiong-Li Liu'
;guizhou university
China
;
_audit_update_record             
;
2020-03-29 deposited with the CCDC.	2020-10-20 downloaded from the CCDC.
;
_audit_creation_date             2019-09-12
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2019.08.16 svn.r3652 for OlexSys, GUI svn.r5895)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H13 N O4'
_chemical_formula_sum            'C19 H13 N O4'
_chemical_formula_weight         319.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   4.2074(4)
_cell_length_b                   12.9179(9)
_cell_length_c                   27.180(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.001(7)
_cell_angle_gamma                90
_cell_volume                     1473.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2668
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.2030
_cell_measurement_theta_min      3.7550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.843
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.16827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_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  0.0505
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            6110
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.334
_diffrn_reflns_theta_min         3.260
_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 0.999
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      6.00  32.00   1.00    1.00    --  -40.98  57.00  90.00   26
  2  ω    -63.00  -9.00   1.00    1.00    --  -40.98  57.00  90.00   54
  3  ω   -107.00 -15.00   1.00    1.00    --  -40.98 -57.00 -60.00   92
  4  ω     29.00  86.00   1.00    1.00    --   40.98-125.00 -90.00   57
  5  ω     29.00  54.00   1.00    1.00    --   40.98-125.00-180.00   25
  6  ω     64.00 117.00   1.00    1.00    --  106.95-125.00  90.00   53
  7  ω     72.00 123.00   1.00    1.00    --  106.95 -45.00 150.00   51
  8  ω     79.00 167.00   1.00    1.00    --  106.95  61.00   0.00   88
  9  ω    116.00 171.00   1.00    1.00    --  106.95 125.00 -30.00   55
 10  ω    104.00 140.00   1.00    1.00    --  106.95  86.00-117.00   36
 11  ω     78.00 165.00   1.00    1.00    --  106.95  61.00 -60.00   87
 12  ω     34.00  63.00   1.00    1.00    --  106.95-125.00  90.00   29
 13  ω     24.00 105.00   1.00    1.00    --  106.95 -94.00 120.00   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      -0.0807716500
_diffrn_orient_matrix_UB_12      0.0529833500
_diffrn_orient_matrix_UB_13      0.0061600000
_diffrn_orient_matrix_UB_21      0.0709198500
_diffrn_orient_matrix_UB_22      0.0028747500
_diffrn_orient_matrix_UB_23      0.0537105000
_diffrn_orient_matrix_UB_31      0.1485879500
_diffrn_orient_matrix_UB_32      0.0272552500
_diffrn_orient_matrix_UB_33      -0.0175543000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                2485
_reflns_number_total             2894
_reflns_odcompleteness_completeness 99.94
_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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT 2018/3 (Sheldrick, 2015)'
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       0.0039(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2894
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0845
_refine_ls_R_factor_gt           0.0771
_refine_ls_restrained_S_all      1.133
_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)+(0.1071P)²+2.3602P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2231
_refine_ls_wR_factor_ref         0.2291
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Riding coordinates:
 O4(H4)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4A), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15),
 C16(H16), C17(H17), C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   mixed
_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 -0.2402(5) -1.09280(18) -0.66690(8) 0.0282(6) Uani 1 1 d . . . . .
O2 O 0.0524(6) -1.20435(17) -0.70190(9) 0.0353(6) Uani 1 1 d . . . . .
O3 O 0.5740(6) -1.10283(17) -0.84401(8) 0.0300(6) Uani 1 1 d . . . . .
O4 O 0.8026(6) -1.06315(18) -0.92737(9) 0.0321(6) Uani 1 1 d . . . . .
H4 H 0.761892 -1.099782 -0.903922 0.048 Uiso 1 1 d R U . . .
N1 N -0.0279(6) -1.11511(19) -0.69339(9) 0.0226(6) Uani 1 1 d . . . . .
C1 C 0.2273(7) -1.0535(2) -0.76479(11) 0.0211(6) Uani 1 1 d . . . . .
H1 H 0.187604 -1.120230 -0.778628 0.025 Uiso 1 1 calc R U . . .
C2 C 0.1359(7) -1.0310(2) -0.71784(11) 0.0197(6) Uani 1 1 d . . . . .
C3 C 0.1970(7) -0.9358(2) -0.69452(10) 0.0196(6) Uani 1 1 d . . . . .
C4 C 0.3453(7) -0.8615(2) -0.72211(11) 0.0224(6) Uani 1 1 d . . . . .
H4A H 0.385316 -0.794826 -0.708238 0.027 Uiso 1 1 calc R U . . .
C5 C 0.4373(7) -0.8819(2) -0.76968(11) 0.0220(7) Uani 1 1 d . . . . .
H5 H 0.541652 -0.829858 -0.787247 0.026 Uiso 1 1 calc R U . . .
C6 C 0.3767(7) -0.9784(2) -0.79142(11) 0.0212(6) Uani 1 1 d . . . . .
C7 C 0.4903(7) -1.0108(2) -0.84040(11) 0.0225(7) Uani 1 1 d . . . . .
C8 C 0.5053(7) -0.9390(2) -0.88173(11) 0.0216(7) Uani 1 1 d . . . . .
C9 C 0.3580(7) -0.8409(2) -0.88247(11) 0.0239(7) Uani 1 1 d . . . . .
H9 H 0.245766 -0.819639 -0.855048 0.029 Uiso 1 1 calc R U . . .
C10 C 0.3735(8) -0.7753(2) -0.92212(12) 0.0269(7) Uani 1 1 d . . . . .
H10 H 0.276221 -0.708953 -0.921751 0.032 Uiso 1 1 calc R U . . .
C11 C 0.5337(8) -0.8070(3) -0.96304(12) 0.0275(7) Uani 1 1 d . . . . .
H11 H 0.543021 -0.761937 -0.990537 0.033 Uiso 1 1 calc R U . . .
C12 C 0.6776(8) -0.9025(3) -0.96387(12) 0.0276(7) Uani 1 1 d . . . . .
H12 H 0.787137 -0.922755 -0.991726 0.033 Uiso 1 1 calc R U . . .
C13 C 0.6633(7) -0.9694(2) -0.92415(11) 0.0240(7) Uani 1 1 d . . . . .
C14 C 0.1313(7) -0.9124(2) -0.64237(11) 0.0207(6) Uani 1 1 d . . . . .
C15 C 0.2344(7) -0.9793(2) -0.60444(11) 0.0247(7) Uani 1 1 d . . . . .
H15 H 0.338810 -1.042153 -0.611717 0.030 Uiso 1 1 calc R U . . .
C16 C 0.1843(8) -0.9540(3) -0.55569(12) 0.0294(7) Uani 1 1 d . . . . .
H16 H 0.255442 -0.999499 -0.529775 0.035 Uiso 1 1 calc R U . . .
C17 C 0.0312(8) -0.8627(3) -0.54491(12) 0.0302(8) Uani 1 1 d . . . . .
H17 H -0.003615 -0.846081 -0.511656 0.036 Uiso 1 1 calc R U . . .
C18 C -0.0715(8) -0.7954(3) -0.58241(12) 0.0282(7) Uani 1 1 d . . . . .
H18 H -0.177162 -0.732963 -0.574979 0.034 Uiso 1 1 calc R U . . .
C19 C -0.0186(7) -0.8201(2) -0.63133(12) 0.0243(7) Uani 1 1 d . . . . .
H19 H -0.085197 -0.773552 -0.657091 0.029 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.220(3) . ?
O2 N1 1.228(3) . ?
O3 C7 1.246(4) . ?
O4 H4 0.8214 . ?
O4 C13 1.351(4) . ?
N1 C2 1.470(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.389(4) . ?
C1 C6 1.387(4) . ?
C2 C3 1.399(4) . ?
C3 C4 1.393(4) . ?
C3 C14 1.494(4) . ?
C4 H4A 0.9500 . ?
C4 C5 1.401(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.395(4) . ?
C6 C7 1.505(4) . ?
C7 C8 1.462(4) . ?
C8 C9 1.410(4) . ?
C8 C13 1.426(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.376(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.401(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.376(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(4) . ?
C14 C15 1.391(4) . ?
C14 C19 1.392(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.395(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.385(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.400(4) . ?
C19 H19 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
C13 O4 H4 110.5 . . ?
O1 N1 O2 123.7(3) . . ?
O1 N1 C2 118.5(2) . . ?
O2 N1 C2 117.7(2) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C6 C1 C2 119.8(3) . . ?
C1 C2 N1 115.4(3) . . ?
C1 C2 C3 123.1(3) . . ?
C3 C2 N1 121.5(2) . . ?
C2 C3 C14 124.6(3) . . ?
C4 C3 C2 115.9(3) . . ?
C4 C3 C14 119.4(3) . . ?
C3 C4 H4A 119.0 . . ?
C3 C4 C5 122.0(3) . . ?
C5 C4 H4A 119.0 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.7(3) . . ?
C1 C6 C7 116.8(3) . . ?
C5 C6 C7 124.2(3) . . ?
O3 C7 C6 116.3(3) . . ?
O3 C7 C8 121.2(3) . . ?
C8 C7 C6 122.5(3) . . ?
C9 C8 C7 122.6(3) . . ?
C9 C8 C13 117.8(3) . . ?
C13 C8 C7 119.6(3) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.3(3) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.6(3) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 119.9 . . ?
C11 C12 C13 120.2(3) . . ?
C13 C12 H12 119.9 . . ?
O4 C13 C8 121.9(3) . . ?
O4 C13 C12 117.7(3) . . ?
C12 C13 C8 120.3(3) . . ?
C15 C14 C3 120.6(3) . . ?
C15 C14 C19 119.7(3) . . ?
C19 C14 C3 119.6(3) . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.8(3) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.3(3) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.6(3) . . ?
C19 C18 H18 120.2 . . ?
C14 C19 C18 120.3(3) . . ?
C14 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C2 C1 -144.7(3) . . . . ?
O1 N1 C2 C3 36.1(4) . . . . ?
O2 N1 C2 C1 33.5(4) . . . . ?
O2 N1 C2 C3 -145.7(3) . . . . ?
O3 C7 C8 C9 167.6(3) . . . . ?
O3 C7 C8 C13 -9.9(5) . . . . ?
N1 C2 C3 C4 -178.2(3) . . . . ?
N1 C2 C3 C14 5.4(4) . . . . ?
C1 C2 C3 C4 2.7(4) . . . . ?
C1 C2 C3 C14 -173.7(3) . . . . ?
C1 C6 C7 O3 -31.0(4) . . . . ?
C1 C6 C7 C8 149.4(3) . . . . ?
C2 C1 C6 C5 1.3(4) . . . . ?
C2 C1 C6 C7 175.6(3) . . . . ?
C2 C3 C4 C5 -2.1(4) . . . . ?
C2 C3 C14 C15 49.5(4) . . . . ?
C2 C3 C14 C19 -134.2(3) . . . . ?
C3 C4 C5 C6 1.2(5) . . . . ?
C3 C14 C15 C16 177.0(3) . . . . ?
C3 C14 C19 C18 -177.7(3) . . . . ?
C4 C3 C14 C15 -126.8(3) . . . . ?
C4 C3 C14 C19 49.5(4) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
C4 C5 C6 C7 -174.6(3) . . . . ?
C5 C6 C7 O3 143.0(3) . . . . ?
C5 C6 C7 C8 -36.6(5) . . . . ?
C6 C1 C2 N1 178.5(3) . . . . ?
C6 C1 C2 C3 -2.4(5) . . . . ?
C6 C7 C8 C9 -12.9(5) . . . . ?
C6 C7 C8 C13 169.7(3) . . . . ?
C7 C8 C9 C10 -179.4(3) . . . . ?
C7 C8 C13 O4 -0.4(5) . . . . ?
C7 C8 C13 C12 179.5(3) . . . . ?
C8 C9 C10 C11 1.2(5) . . . . ?
C9 C8 C13 O4 -178.0(3) . . . . ?
C9 C8 C13 C12 1.9(5) . . . . ?
C9 C10 C11 C12 -0.5(5) . . . . ?
C10 C11 C12 C13 0.6(5) . . . . ?
C11 C12 C13 O4 178.6(3) . . . . ?
C11 C12 C13 C8 -1.3(5) . . . . ?
C13 C8 C9 C10 -1.9(5) . . . . ?
C14 C3 C4 C5 174.5(3) . . . . ?
C14 C15 C16 C17 0.2(5) . . . . ?
C15 C14 C19 C18 -1.3(5) . . . . ?
C15 C16 C17 C18 -0.5(5) . . . . ?
C16 C17 C18 C19 -0.2(5) . . . . ?
C17 C18 C19 C14 1.1(5) . . . . ?
C19 C14 C15 C16 0.7(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
;
_oxdiff_exptl_absorpt_empirical_full_max 3.405
_oxdiff_exptl_absorpt_empirical_full_min 0.256
####################################################################### 
# 
# 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_hxw-18-02
_database_code_depnum_ccdc_archive 'CCDC 1993372'
loop_
_audit_author_name
_audit_author_address
'Xiong-Li Liu'
;guizhou university
China
;
_audit_update_record             
;
2020-03-29 deposited with the CCDC.	2020-10-20 downloaded from the CCDC.
;
_audit_creation_date             2019-09-12
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2019.08.16 svn.r3652 for OlexSys, GUI svn.r5895)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H12 Br N O4'
_chemical_formula_sum            'C19 H12 Br N O4'
_chemical_formula_weight         398.21
_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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   12.5309(7)
_cell_length_b                   7.1686(4)
_cell_length_c                   17.8685(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.845(5)
_cell_angle_gamma                90
_cell_volume                     1599.37(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2488
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.1360
_cell_measurement_theta_min      2.6700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.595
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_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  0.0314
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6396
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.288
_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     -1.00  84.00   1.00    2.00    --   11.74  57.00  90.00   85
  2  ω    -54.00  43.00   1.00    2.00    --   11.74 -77.00 -30.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0152696000
_diffrn_orient_matrix_UB_12      0.0155040000
_diffrn_orient_matrix_UB_13      -0.0368007000
_diffrn_orient_matrix_UB_21      0.0545591000
_diffrn_orient_matrix_UB_22      -0.0123840000
_diffrn_orient_matrix_UB_23      0.0131764000
_diffrn_orient_matrix_UB_31      -0.0045113000
_diffrn_orient_matrix_UB_32      -0.0969517000
_diffrn_orient_matrix_UB_33      -0.0075540000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2367
_reflns_number_total             2818
_reflns_odcompleteness_completeness 99.92
_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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS 2018/3 (Sheldrick, 2008)'
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.071
_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     227
_refine_ls_number_reflns         2818
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0328
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0307P)²+0.2318P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0683
_refine_ls_wR_factor_ref         0.0725
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C15(H15), C12(H12), C2(H2), C9(H9), C17(H17), C16(H16), C4(H4),
 C19(H19), C5(H5), C18(H18)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.07517(2) 0.93971(4) 0.27717(2) 0.02623(12) Uani 1 1 d . . . . .
O1 O 1.04845(13) 0.7082(2) 0.59813(9) 0.0192(4) Uani 1 1 d . . . . .
H1 H 0.986111 0.699115 0.608398 0.029 Uiso 1 1 calc R U . . .
O2 O 0.84469(14) 0.6822(2) 0.56956(10) 0.0210(4) Uani 1 1 d . . . . .
O4 O 0.42116(15) 0.9163(3) 0.41190(13) 0.0332(5) Uani 1 1 d . . . . .
O3 O 0.44190(15) 0.7525(3) 0.51406(11) 0.0416(6) Uani 1 1 d . . . . .
N1 N 0.46828(17) 0.8006(3) 0.45273(14) 0.0246(6) Uani 1 1 d . . . . .
C13 C 0.7543(2) 0.5855(3) 0.38002(15) 0.0159(6) Uani 1 1 d . . . . .
H13 H 0.818127 0.540945 0.363756 0.019 Uiso 1 1 calc R U . . .
C15 C 0.3670(2) 0.5385(3) 0.33647(15) 0.0171(6) Uani 1 1 d . . . . .
H15 H 0.366481 0.513405 0.387502 0.021 Uiso 1 1 calc R U . . .
C8 C 0.75546(19) 0.6751(3) 0.44903(14) 0.0153(6) Uani 1 1 d . . . . .
C1 C 0.95833(19) 0.7494(3) 0.47414(14) 0.0142(6) Uani 1 1 d . . . . .
C6 C 1.0506(2) 0.7491(3) 0.52495(14) 0.0160(6) Uani 1 1 d . . . . .
C3 C 1.0659(2) 0.8546(3) 0.37681(14) 0.0163(6) Uani 1 1 d . . . . .
C14 C 0.4616(2) 0.5971(3) 0.30749(15) 0.0148(6) Uani 1 1 d . . . . .
C11 C 0.5619(2) 0.6264(3) 0.35669(15) 0.0155(6) Uani 1 1 d . . . . .
C12 C 0.6603(2) 0.5614(3) 0.33525(15) 0.0166(6) Uani 1 1 d . . . . .
H12 H 0.662151 0.500349 0.289463 0.020 Uiso 1 1 calc R U . . .
C2 C 0.9679(2) 0.8062(3) 0.40009(14) 0.0154(6) Uani 1 1 d . . . . .
H2 H 0.907328 0.811233 0.366293 0.018 Uiso 1 1 calc R U . . .
C7 C 0.8532(2) 0.7012(3) 0.50184(14) 0.0154(6) Uani 1 1 d . . . . .
C10 C 0.56647(19) 0.7149(3) 0.42643(15) 0.0167(6) Uani 1 1 d . . . . .
C9 C 0.65835(19) 0.7384(3) 0.47313(15) 0.0162(6) Uani 1 1 d . . . . .
H9 H 0.656085 0.795070 0.519782 0.019 Uiso 1 1 calc R U . . .
C17 C 0.2749(2) 0.5523(3) 0.21356(16) 0.0210(6) Uani 1 1 d . . . . .
H17 H 0.211934 0.541722 0.182351 0.025 Uiso 1 1 calc R U . . .
C16 C 0.2741(2) 0.5175(4) 0.28964(16) 0.0214(6) Uani 1 1 d . . . . .
H16 H 0.211203 0.479929 0.309308 0.026 Uiso 1 1 calc R U . . .
C4 C 1.1579(2) 0.8457(4) 0.42598(15) 0.0181(6) Uani 1 1 d . . . . .
H4 H 1.224179 0.874898 0.409327 0.022 Uiso 1 1 calc R U . . .
C19 C 0.4620(2) 0.6256(3) 0.23069(15) 0.0170(6) Uani 1 1 d . . . . .
H19 H 0.525152 0.660097 0.210550 0.020 Uiso 1 1 calc R U . . .
C5 C 1.1502(2) 0.7935(3) 0.49914(15) 0.0186(6) Uani 1 1 d . . . . .
H5 H 1.211750 0.787516 0.532030 0.022 Uiso 1 1 calc R U . . .
C18 C 0.3691(2) 0.6029(3) 0.18379(16) 0.0191(6) Uani 1 1 d . . . . .
H18 H 0.370085 0.621729 0.132349 0.023 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 C3 1.895(2) . ?
O1 H1 0.8200 . ?
O1 C6 1.343(3) . ?
O2 C7 1.231(3) . ?
O4 N1 1.223(3) . ?
O3 N1 1.221(3) . ?
N1 C10 1.487(3) . ?
C13 H13 0.9300 . ?
C13 C8 1.389(3) . ?
C13 C12 1.378(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.398(3) . ?
C15 C16 1.383(4) . ?
C8 C7 1.494(4) . ?
C8 C9 1.400(3) . ?
C1 C6 1.409(3) . ?
C1 C2 1.399(3) . ?
C1 C7 1.487(3) . ?
C6 C5 1.403(3) . ?
C3 C2 1.374(3) . ?
C3 C4 1.390(4) . ?
C14 C11 1.486(4) . ?
C14 C19 1.388(4) . ?
C11 C12 1.401(3) . ?
C11 C10 1.395(4) . ?
C12 H12 0.9300 . ?
C2 H2 0.9300 . ?
C10 C9 1.374(4) . ?
C9 H9 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.383(4) . ?
C17 C18 1.384(4) . ?
C16 H16 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.371(4) . ?
C19 H19 0.9300 . ?
C19 C18 1.385(4) . ?
C5 H5 0.9300 . ?
C18 H18 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
C6 O1 H1 109.5 . . ?
O4 N1 C10 117.5(2) . . ?
O3 N1 O4 125.0(2) . . ?
O3 N1 C10 117.5(3) . . ?
C8 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C12 C13 C8 121.1(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C16 C15 C14 120.4(3) . . ?
C13 C8 C7 124.4(2) . . ?
C13 C8 C9 118.6(2) . . ?
C9 C8 C7 116.9(2) . . ?
C6 C1 C7 119.2(2) . . ?
C2 C1 C6 118.6(2) . . ?
C2 C1 C7 122.1(2) . . ?
O1 C6 C1 123.0(2) . . ?
O1 C6 C5 117.5(2) . . ?
C5 C6 C1 119.5(2) . . ?
C2 C3 Br1 119.5(2) . . ?
C2 C3 C4 120.8(2) . . ?
C4 C3 Br1 119.69(18) . . ?
C15 C14 C11 121.6(2) . . ?
C19 C14 C15 119.0(3) . . ?
C19 C14 C11 119.4(2) . . ?
C12 C11 C14 120.7(2) . . ?
C10 C11 C14 124.1(2) . . ?
C10 C11 C12 115.1(2) . . ?
C13 C12 C11 121.9(2) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.7 . . ?
O2 C7 C8 118.2(2) . . ?
O2 C7 C1 120.4(2) . . ?
C1 C7 C8 121.4(2) . . ?
C11 C10 N1 119.9(2) . . ?
C9 C10 N1 115.5(2) . . ?
C9 C10 C11 124.5(2) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 C8 118.6(2) . . ?
C10 C9 H9 120.7 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.1(3) . . ?
C18 C17 H17 119.9 . . ?
C15 C16 C17 120.0(2) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
C14 C19 H19 119.7 . . ?
C18 C19 C14 120.5(2) . . ?
C18 C19 H19 119.7 . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5 119.6 . . ?
C17 C18 C19 119.9(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.229
_oxdiff_exptl_absorpt_empirical_full_min 0.814
