# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_201906142
_database_code_depnum_ccdc_archive 'CCDC 1941066'
loop_
_audit_author_name
_audit_author_address
'chuanwen lei'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-12-23 downloaded from the CCDC.
;
_audit_creation_date             2019-06-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H12 N2 O5'
_chemical_formula_sum            'C20 H12 N2 O5'
_chemical_formula_weight         360.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4Br1
_chemical_oxdiff_usercomment     1
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                   13.8403(2)
_cell_length_b                   13.0587(2)
_cell_length_c                   10.6561(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.985(2)
_cell_angle_gamma                90
_cell_volume                     1809.98(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3032
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8100
_cell_measurement_theta_min      4.7840
_shelx_estimated_absorpt_T_max   0.923
_shelx_estimated_absorpt_T_min   0.881
_exptl_absorpt_coefficient_mu    0.811
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6709
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         3.398
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -2.00   36.00   0.5000    1.4000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000    0.0000 76

#__ type_ start__ end____ width___ exp.time_
  2 omega  -92.00  -33.00   0.5000    1.4000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  120.0000 118

#__ type_ start__ end____ width___ exp.time_
  3 omega  -19.00    7.00   0.5000    1.4000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -30.0000 52

#__ type_ start__ end____ width___ exp.time_
  4 omega   -9.00   32.00   0.5000    1.4000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000 -180.0000 82

#__ type_ start__ end____ width___ exp.time_
  5 omega  -49.00  -21.00   0.5000    1.4000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000  -30.0000 56

#__ type_ start__ end____ width___ exp.time_
  6 omega   -3.00   37.00   0.5000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -30.0000 80

#__ type_ start__ end____ width___ exp.time_
  7 omega  -27.00   47.00   0.5000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000    0.0000 148

#__ type_ start__ end____ width___ exp.time_
  8 omega   47.00   77.00   0.5000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -30.0000 60

#__ type_ start__ end____ width___ exp.time_
  9 omega   37.00   76.00   0.5000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -60.0000 78

#__ type_ start__ end____ width___ exp.time_
 10 omega   80.00  105.00   0.5000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -30.0000 50

#__ type_ start__ end____ width___ exp.time_
 11 omega  142.00  177.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 70

#__ type_ start__ end____ width___ exp.time_
 12 omega   43.00   81.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 76

#__ type_ start__ end____ width___ exp.time_
 13 omega   88.00  123.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 70

#__ type_ start__ end____ width___ exp.time_
 14 omega   71.00  110.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 78

#__ type_ start__ end____ width___ exp.time_
 15 omega   49.00  114.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 130

#__ type_ start__ end____ width___ exp.time_
 16 omega   41.00   95.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 108

#__ type_ start__ end____ width___ exp.time_
 17 omega   44.00   69.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 50

#__ type_ start__ end____ width___ exp.time_
 18 omega  101.00  167.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 132

#__ type_ start__ end____ width___ exp.time_
 19 omega   86.00  165.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -180.0000 158

#__ type_ start__ end____ width___ exp.time_
 20 omega   53.00  115.00   0.5000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -120.0000 124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0438429000
_diffrn_orient_matrix_UB_12      0.0976544000
_diffrn_orient_matrix_UB_13      -0.0804509000
_diffrn_orient_matrix_UB_21      -0.0461171000
_diffrn_orient_matrix_UB_22      -0.0649675000
_diffrn_orient_matrix_UB_23      -0.1272128000
_diffrn_orient_matrix_UB_31      -0.0998897000
_diffrn_orient_matrix_UB_32      -0.0128821000
_diffrn_orient_matrix_UB_33      0.0316918000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2670
_reflns_number_total             3234
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0024(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.031
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1388
_refine_ls_wR_factor_ref         0.1509
_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 Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.90555(13) 0.60709(13) -0.02854(18) 0.0478(4) Uani 1 1 d . . . . .
C2 C 1.06677(13) 0.62068(12) 0.18719(19) 0.0483(4) Uani 1 1 d . . . . .
C3 C 0.95670(12) 0.61251(12) 0.11671(17) 0.0449(4) Uani 1 1 d . . . . .
C4 C 0.88748(12) 0.60874(12) 0.18031(17) 0.0423(4) Uani 1 1 d . . . . .
C5 C 0.91864(12) 0.61773(11) 0.32247(17) 0.0436(4) Uani 1 1 d . . . . .
C6 C 1.02458(13) 0.62841(12) 0.39014(18) 0.0465(4) Uani 1 1 d . . . . .
C7 C 1.06539(14) 0.63713(15) 0.52769(19) 0.0555(4) Uani 1 1 d . . . . .
H7 H 1.1359 0.6442 0.5707 0.067 Uiso 1 1 calc R . . . .
C8 C 0.99961(16) 0.63507(14) 0.59963(18) 0.0570(4) Uani 1 1 d . . . . .
H8 H 1.0260 0.6402 0.6922 0.068 Uiso 1 1 calc R . . . .
C9 C 0.89390(15) 0.62536(14) 0.53539(19) 0.0553(4) Uani 1 1 d . . . . .
H9 H 0.8503 0.6244 0.5852 0.066 Uiso 1 1 calc R . . . .
C10 C 0.85395(14) 0.61722(13) 0.39941(19) 0.0504(4) Uani 1 1 d . . . . .
H10 H 0.7832 0.6113 0.3574 0.061 Uiso 1 1 calc R . . . .
C11 C 0.69920(12) 0.66899(14) 0.09045(18) 0.0517(4) Uani 1 1 d . . . . .
C12 C 0.78064(11) 0.58934(13) 0.08012(16) 0.0446(4) Uani 1 1 d . . . . .
C13 C 0.73600(11) 0.48922(13) 0.10563(15) 0.0446(4) Uani 1 1 d . . . . .
C14 C 0.64909(12) 0.51081(14) 0.13880(16) 0.0495(4) Uani 1 1 d . . . . .
C15 C 0.59492(15) 0.43368(18) 0.1739(2) 0.0660(5) Uani 1 1 d . . . . .
H15 H 0.5370 0.4477 0.1964 0.079 Uiso 1 1 calc R . . . .
C16 C 0.63069(17) 0.33419(19) 0.1743(3) 0.0741(6) Uani 1 1 d . . . . .
H16 H 0.5961 0.2810 0.1986 0.089 Uiso 1 1 calc R . . . .
C17 C 0.71567(15) 0.31157(17) 0.1398(2) 0.0645(5) Uani 1 1 d . . . . .
H17 H 0.7370 0.2440 0.1405 0.077 Uiso 1 1 calc R . . . .
C18 C 0.76959(13) 0.38986(14) 0.10405(18) 0.0514(4) Uani 1 1 d . . . . .
H18 H 0.8266 0.3756 0.0798 0.062 Uiso 1 1 calc R . . . .
C19 C 0.72444(16) 0.5866(2) -0.1669(2) 0.0755(7) Uani 1 1 d . . . . .
H19 H 0.7419 0.5871 -0.2437 0.091 Uiso 1 1 calc R . . . .
C20 C 0.54774(15) 0.6665(2) 0.1639(2) 0.0725(6) Uani 1 1 d . . . . .
H20A H 0.4832 0.6350 0.1147 0.109 Uiso 1 1 calc GR . . . .
H20B H 0.5455 0.7378 0.1411 0.109 Uiso 1 1 calc GR . . . .
H20C H 0.5603 0.6596 0.2579 0.109 Uiso 1 1 calc GR . . . .
N1 N 0.80024(11) 0.59600(12) -0.04588(14) 0.0497(4) Uani 1 1 d . . . . .
N2 N 0.63013(11) 0.61646(13) 0.13075(15) 0.0533(4) Uani 1 1 d . . . . .
O1 O 0.94006(10) 0.61145(11) -0.11818(14) 0.0603(4) Uani 1 1 d . . . . .
O2 O 1.13377(10) 0.62059(11) 0.14007(15) 0.0626(4) Uani 1 1 d . . . . .
O3 O 1.09432(9) 0.62912(10) 0.32366(14) 0.0541(3) Uani 1 1 d . . . . .
O4 O 0.70011(11) 0.75912(12) 0.06919(18) 0.0747(4) Uani 1 1 d . . . . .
O5 O 0.63561(11) 0.5776(2) -0.17731(16) 0.1068(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.467(2) . ?
C1 N1 1.413(2) . ?
C1 O1 1.207(2) . ?
C2 C3 1.454(2) . ?
C2 O2 1.196(2) . ?
C2 O3 1.376(2) . ?
C3 C4 1.350(2) . ?
C4 C5 1.431(2) . ?
C4 C12 1.520(2) . ?
C5 C6 1.402(3) . ?
C5 C10 1.406(2) . ?
C6 C7 1.384(3) . ?
C6 O3 1.379(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.376(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.393(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.367(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.565(2) . ?
C11 N2 1.360(2) . ?
C11 O4 1.200(2) . ?
C12 C13 1.510(2) . ?
C12 N1 1.460(2) . ?
C13 C14 1.394(2) . ?
C13 C18 1.380(3) . ?
C14 C15 1.382(3) . ?
C14 N2 1.402(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.390(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.379(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.394(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C19 N1 1.362(3) . ?
C19 O5 1.202(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20 N2 1.459(2) . ?

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
N1 C1 C3 104.31(13) . . ?
O1 C1 C3 130.85(16) . . ?
O1 C1 N1 124.84(17) . . ?
O2 C2 C3 127.51(18) . . ?
O2 C2 O3 117.99(16) . . ?
O3 C2 C3 114.51(14) . . ?
C2 C3 C1 126.23(15) . . ?
C4 C3 C1 111.00(15) . . ?
C4 C3 C2 122.76(16) . . ?
C3 C4 C5 121.30(15) . . ?
C3 C4 C12 109.89(14) . . ?
C5 C4 C12 128.75(14) . . ?
C6 C5 C4 115.87(15) . . ?
C6 C5 C10 117.58(17) . . ?
C10 C5 C4 126.55(16) . . ?
C7 C6 C5 121.97(16) . . ?
O3 C6 C5 121.94(16) . . ?
O3 C6 C7 116.09(16) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 C6 118.69(17) . . ?
C8 C7 H7 120.7 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.77(17) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.29(17) . . ?
C10 C9 H9 119.9 . . ?
C5 C10 H10 119.7 . . ?
C9 C10 C5 120.68(17) . . ?
C9 C10 H10 119.7 . . ?
N2 C11 C12 106.73(15) . . ?
O4 C11 C12 125.77(16) . . ?
O4 C11 N2 127.48(17) . . ?
C4 C12 C11 113.01(14) . . ?
C13 C12 C4 112.18(13) . . ?
C13 C12 C11 102.35(12) . . ?
N1 C12 C4 101.19(12) . . ?
N1 C12 C11 112.94(14) . . ?
N1 C12 C13 115.66(14) . . ?
C14 C13 C12 108.20(14) . . ?
C18 C13 C12 130.65(14) . . ?
C18 C13 C14 121.12(16) . . ?
C13 C14 N2 110.09(15) . . ?
C15 C14 C13 121.11(18) . . ?
C15 C14 N2 128.81(16) . . ?
C14 C15 H15 121.4 . . ?
C14 C15 C16 117.16(18) . . ?
C16 C15 H15 121.4 . . ?
C15 C16 H16 118.8 . . ?
C17 C16 C15 122.35(19) . . ?
C17 C16 H16 118.8 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.1(2) . . ?
C18 C17 H17 120.0 . . ?
C13 C18 C17 118.17(17) . . ?
C13 C18 H18 120.9 . . ?
C17 C18 H18 120.9 . . ?
N1 C19 H19 119.0 . . ?
O5 C19 H19 119.0 . . ?
O5 C19 N1 121.95(19) . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
C1 N1 C12 113.17(14) . . ?
C19 N1 C1 124.04(15) . . ?
C19 N1 C12 122.70(14) . . ?
C11 N2 C14 112.25(14) . . ?
C11 N2 C20 122.88(18) . . ?
C14 N2 C20 124.86(17) . . ?
C2 O3 C6 123.55(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C3 C4 C5 -176.98(14) . . . . ?
C1 C3 C4 C12 5.68(19) . . . . ?
C2 C3 C4 C5 3.1(2) . . . . ?
C2 C3 C4 C12 -174.21(15) . . . . ?
C3 C1 N1 C12 -2.56(19) . . . . ?
C3 C1 N1 C19 -179.1(2) . . . . ?
C3 C2 O3 C6 1.0(2) . . . . ?
C3 C4 C5 C6 -1.3(2) . . . . ?
C3 C4 C5 C10 178.51(15) . . . . ?
C3 C4 C12 C11 -127.73(15) . . . . ?
C3 C4 C12 C13 117.17(15) . . . . ?
C3 C4 C12 N1 -6.70(17) . . . . ?
C4 C5 C6 C7 -179.54(15) . . . . ?
C4 C5 C6 O3 -0.6(2) . . . . ?
C4 C5 C10 C9 179.29(16) . . . . ?
C4 C12 C13 C14 116.10(15) . . . . ?
C4 C12 C13 C18 -61.8(2) . . . . ?
C4 C12 N1 C1 5.53(18) . . . . ?
C4 C12 N1 C19 -177.9(2) . . . . ?
C5 C4 C12 C11 55.2(2) . . . . ?
C5 C4 C12 C13 -59.9(2) . . . . ?
C5 C4 C12 N1 176.21(15) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C5 C6 O3 C2 0.7(2) . . . . ?
C6 C5 C10 C9 -0.9(2) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
C7 C6 O3 C2 179.67(15) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C8 C9 C10 C5 0.5(3) . . . . ?
C10 C5 C6 C7 0.7(2) . . . . ?
C10 C5 C6 O3 179.57(14) . . . . ?
C11 C12 C13 C14 -5.33(17) . . . . ?
C11 C12 C13 C18 176.74(17) . . . . ?
C11 C12 N1 C1 126.62(15) . . . . ?
C11 C12 N1 C19 -56.8(3) . . . . ?
C12 C4 C5 C6 175.54(15) . . . . ?
C12 C4 C5 C10 -4.7(3) . . . . ?
C12 C11 N2 C14 -4.8(2) . . . . ?
C12 C11 N2 C20 174.01(17) . . . . ?
C12 C13 C14 C15 -176.80(17) . . . . ?
C12 C13 C14 N2 2.90(19) . . . . ?
C12 C13 C18 C17 176.14(17) . . . . ?
C13 C12 N1 C1 -115.93(16) . . . . ?
C13 C12 N1 C19 60.6(2) . . . . ?
C13 C14 C15 C16 -0.2(3) . . . . ?
C13 C14 N2 C11 1.3(2) . . . . ?
C13 C14 N2 C20 -177.42(17) . . . . ?
C14 C13 C18 C17 -1.6(3) . . . . ?
C14 C15 C16 C17 -0.8(3) . . . . ?
C15 C14 N2 C11 -179.00(19) . . . . ?
C15 C14 N2 C20 2.2(3) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C16 C17 C18 C13 0.6(3) . . . . ?
C18 C13 C14 C15 1.4(3) . . . . ?
C18 C13 C14 N2 -178.93(15) . . . . ?
N1 C1 C3 C2 177.82(15) . . . . ?
N1 C1 C3 C4 -2.07(19) . . . . ?
N1 C12 C13 C14 -128.55(15) . . . . ?
N1 C12 C13 C18 53.5(2) . . . . ?
N2 C11 C12 C4 -114.80(16) . . . . ?
N2 C11 C12 C13 6.05(17) . . . . ?
N2 C11 C12 N1 131.09(15) . . . . ?
N2 C14 C15 C16 -179.8(2) . . . . ?
O1 C1 C3 C2 -2.8(3) . . . . ?
O1 C1 C3 C4 177.33(18) . . . . ?
O1 C1 N1 C12 178.00(17) . . . . ?
O1 C1 N1 C19 1.5(3) . . . . ?
O2 C2 C3 C1 -3.0(3) . . . . ?
O2 C2 C3 C4 176.91(16) . . . . ?
O2 C2 O3 C6 -178.86(15) . . . . ?
O3 C2 C3 C1 177.21(15) . . . . ?
O3 C2 C3 C4 -2.9(2) . . . . ?
O3 C6 C7 C8 -178.87(16) . . . . ?
O4 C11 C12 C4 63.8(2) . . . . ?
O4 C11 C12 C13 -175.35(19) . . . . ?
O4 C11 C12 N1 -50.3(3) . . . . ?
O4 C11 N2 C14 176.7(2) . . . . ?
O4 C11 N2 C20 -4.5(3) . . . . ?
O5 C19 N1 C1 -179.8(3) . . . . ?
O5 C19 N1 C12 4.1(4) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.500 0.000 0.000 140.9 48.1 ?
2 0.500 0.500 0.500 140.9 48.1 ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_201905121
_database_code_depnum_ccdc_archive 'CCDC 1941067'
loop_
_audit_author_name
_audit_author_address
'chuanwen lei'
;University of Chinese Academy of Sciences
China
;
_audit_update_record             
;
2019-07-17 deposited with the CCDC.	2019-12-23 downloaded from the CCDC.
;
_audit_creation_date             2019-05-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H11 N O5'
_chemical_formula_sum            'C19 H11 N O5'
_chemical_formula_weight         333.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O4
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.86044(13)
_cell_length_b                   16.5893(3)
_cell_length_c                   20.7763(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3053.87(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4386
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9090
_cell_measurement_theta_min      4.2430
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.863
_exptl_absorpt_coefficient_mu    0.893
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85576
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.450
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12314
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         4.256
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -102.00  -74.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   90.0000 56

#__ type_ start__ end____ width___ exp.time_
  2 omega  -48.00  -23.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000 -180.0000 50

#__ type_ start__ end____ width___ exp.time_
  3 omega  -32.00   -6.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000 -150.0000 52

#__ type_ start__ end____ width___ exp.time_
  4 omega  -69.00  -43.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   90.0000 52

#__ type_ start__ end____ width___ exp.time_
  5 omega  -99.00  -53.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000 -150.0000 92

#__ type_ start__ end____ width___ exp.time_
  6 omega   -7.00   34.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000 -180.0000 82

#__ type_ start__ end____ width___ exp.time_
  7 omega   30.00  102.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000   60.0000 144

#__ type_ start__ end____ width___ exp.time_
  8 omega   29.00   66.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   77.0000   90.0000 74

#__ type_ start__ end____ width___ exp.time_
  9 omega   62.00  109.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   30.0000 94

#__ type_ start__ end____ width___ exp.time_
 10 omega   26.00   52.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000 -120.0000 52

#__ type_ start__ end____ width___ exp.time_
 11 omega  -30.00   10.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -57.0000 -120.0000 80

#__ type_ start__ end____ width___ exp.time_
 12 omega    7.00   77.00   0.5000    1.7500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  120.0000 140

#__ type_ start__ end____ width___ exp.time_
 13 omega   37.00  109.00   0.5000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   90.0000 144

#__ type_ start__ end____ width___ exp.time_
 14 omega   91.00  176.00   0.5000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 170

#__ type_ start__ end____ width___ exp.time_
 15 omega   69.00   95.00   0.5000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 52

#__ type_ start__ end____ width___ exp.time_
 16 omega   38.00   78.00   0.5000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 80

#__ type_ start__ end____ width___ exp.time_
 17 omega   39.00   70.00   0.5000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 62

#__ type_ start__ end____ width___ exp.time_
 18 omega   38.00   93.00   0.5000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 110

#__ type_ start__ end____ width___ exp.time_
 19 omega   63.00  104.00   0.5000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 82

#__ type_ start__ end____ width___ exp.time_
 20 omega   57.00   95.00   0.5000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 76

#__ type_ start__ end____ width___ exp.time_
 21 omega   37.00   62.00   0.5000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 50

#__ type_ start__ end____ width___ exp.time_
 22 omega  101.00  127.00   0.5000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 52

#__ type_ start__ end____ width___ exp.time_
 23 omega   76.00  108.00   0.5000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  120.0000 64

#__ type_ start__ end____ width___ exp.time_
 24 omega   88.00  164.00   0.5000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -120.0000 152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0043442000
_diffrn_orient_matrix_UB_12      0.0917082000
_diffrn_orient_matrix_UB_13      0.0115118000
_diffrn_orient_matrix_UB_21      -0.0021817000
_diffrn_orient_matrix_UB_22      -0.0143611000
_diffrn_orient_matrix_UB_23      0.0732462000
_diffrn_orient_matrix_UB_31      0.1738174000
_diffrn_orient_matrix_UB_32      -0.0024696000
_diffrn_orient_matrix_UB_33      0.0006613000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2322
_reflns_number_total             2731
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2731
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      1.026
_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)+(0.0624P)²+0.5916P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1115
_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 Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C15(H15), C16(H16), C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.74072(17) 0.22089(9) 0.62496(7) 0.0393(3) Uani 1 1 d . . . . .
H1 H 0.7916 0.2376 0.5882 0.047 Uiso 1 1 calc R . . . .
C2 C 0.77225(19) 0.14721(10) 0.65173(9) 0.0481(4) Uani 1 1 d . . . . .
H2 H 0.8432 0.1137 0.6325 0.058 Uiso 1 1 calc R . . . .
C3 C 0.6987(2) 0.12231(11) 0.70751(9) 0.0549(5) Uani 1 1 d . . . . .
H3 H 0.7217 0.0725 0.7255 0.066 Uiso 1 1 calc R . . . .
C4 C 0.5921(2) 0.17082(11) 0.73627(9) 0.0541(4) Uani 1 1 d . . . . .
H4 H 0.5436 0.1542 0.7737 0.065 Uiso 1 1 calc R . . . .
C5 C 0.55800(18) 0.24458(10) 0.70883(8) 0.0423(4) Uani 1 1 d . . . . .
C6 C 0.63180(16) 0.27098(9) 0.65309(7) 0.0346(3) Uani 1 1 d . . . . .
C7 C 0.58811(15) 0.34885(9) 0.63064(7) 0.0333(3) Uani 1 1 d . . . . .
C8 C 0.48250(16) 0.39306(9) 0.66089(7) 0.0370(3) Uani 1 1 d . . . . .
C9 C 0.40246(19) 0.36474(11) 0.71722(8) 0.0476(4) Uani 1 1 d . . . . .
C10 C 0.46651(16) 0.47109(9) 0.62880(8) 0.0403(4) Uani 1 1 d . . . . .
C11 C 0.59447(18) 0.35179(9) 0.50882(8) 0.0408(4) Uani 1 1 d . . . . .
C12 C 0.64210(16) 0.39472(9) 0.57287(7) 0.0359(3) Uani 1 1 d . . . . .
C13 C 0.80928(17) 0.40501(9) 0.56480(8) 0.0410(4) Uani 1 1 d . . . . .
C14 C 0.84947(19) 0.37183(10) 0.50587(8) 0.0465(4) Uani 1 1 d . . . . .
C15 C 0.9967(2) 0.37196(13) 0.48542(12) 0.0669(6) Uani 1 1 d . . . . .
H15 H 1.0237 0.3497 0.4460 0.080 Uiso 1 1 calc R . . . .
C16 C 1.1037(2) 0.40625(14) 0.52538(15) 0.0799(8) Uani 1 1 d . . . . .
H16 H 1.2040 0.4079 0.5122 0.096 Uiso 1 1 calc R . . . .
C17 C 1.0648(2) 0.43814(14) 0.58466(14) 0.0743(7) Uani 1 1 d . . . . .
H17 H 1.1391 0.4599 0.6110 0.089 Uiso 1 1 calc R . . . .
C18 C 0.9154(2) 0.43783(11) 0.60506(10) 0.0547(4) Uani 1 1 d . . . . .
H18 H 0.8883 0.4592 0.6448 0.066 Uiso 1 1 calc R . . . .
C19 C 0.7253(3) 0.29866(14) 0.41247(9) 0.0691(6) Uani 1 1 d . . . . .
H19A H 0.7878 0.2515 0.4156 0.104 Uiso 1 1 calc GR . . . .
H19B H 0.7655 0.3343 0.3804 0.104 Uiso 1 1 calc GR . . . .
H19C H 0.6247 0.2831 0.4007 0.104 Uiso 1 1 calc GR . . . .
N1 N 0.72208(16) 0.33977(9) 0.47443(7) 0.0483(4) Uani 1 1 d . . . . .
O1 O 0.44769(14) 0.28989(8) 0.73867(6) 0.0547(3) Uani 1 1 d . . . . .
O2 O 0.30250(17) 0.39832(9) 0.74533(7) 0.0706(4) Uani 1 1 d . . . . .
O3 O 0.39181(13) 0.52881(7) 0.64125(7) 0.0557(3) Uani 1 1 d . . . . .
O4 O 0.56313(12) 0.47055(6) 0.57698(5) 0.0429(3) Uani 1 1 d . . . . .
O5 O 0.46690(13) 0.33312(8) 0.49507(6) 0.0549(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9300 . ?
C1 C2 1.372(2) . ?
C1 C6 1.401(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.392(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(2) . ?
C5 C6 1.400(2) . ?
C5 O1 1.380(2) . ?
C6 C7 1.427(2) . ?
C7 C8 1.345(2) . ?
C7 C12 1.499(2) . ?
C8 C9 1.447(2) . ?
C8 C10 1.463(2) . ?
C9 O1 1.379(2) . ?
C9 O2 1.198(2) . ?
C10 O3 1.1924(19) . ?
C10 O4 1.3755(19) . ?
C11 C12 1.567(2) . ?
C11 N1 1.352(2) . ?
C11 O5 1.2063(19) . ?
C12 C13 1.500(2) . ?
C12 O4 1.4419(17) . ?
C13 C14 1.389(2) . ?
C13 C18 1.371(2) . ?
C14 C15 1.372(2) . ?
C14 N1 1.408(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.383(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.384(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.390(3) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C19 N1 1.457(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 120.0 . . ?
C2 C1 C6 119.98(15) . . ?
C6 C1 H1 120.0 . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.43(16) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.59(16) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.19(17) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 121.04(16) . . ?
O1 C5 C4 116.82(15) . . ?
O1 C5 C6 122.13(15) . . ?
C1 C6 C7 125.97(14) . . ?
C5 C6 C1 118.75(14) . . ?
C5 C6 C7 115.27(14) . . ?
C6 C7 C12 129.39(13) . . ?
C8 C7 C6 121.98(14) . . ?
C8 C7 C12 108.62(13) . . ?
C7 C8 C9 122.82(15) . . ?
C7 C8 C10 109.69(13) . . ?
C9 C8 C10 127.48(14) . . ?
O1 C9 C8 114.30(14) . . ?
O2 C9 C8 127.27(17) . . ?
O2 C9 O1 118.42(16) . . ?
O3 C10 C8 131.71(15) . . ?
O3 C10 O4 121.37(15) . . ?
O4 C10 C8 106.90(12) . . ?
N1 C11 C12 106.89(13) . . ?
O5 C11 C12 124.75(14) . . ?
O5 C11 N1 128.35(16) . . ?
C7 C12 C11 111.29(12) . . ?
C7 C12 C13 117.52(12) . . ?
C13 C12 C11 102.87(12) . . ?
O4 C12 C7 103.92(11) . . ?
O4 C12 C11 108.43(12) . . ?
O4 C12 C13 112.73(12) . . ?
C14 C13 C12 107.85(14) . . ?
C18 C13 C12 130.84(16) . . ?
C18 C13 C14 121.29(16) . . ?
C13 C14 N1 110.67(14) . . ?
C15 C14 C13 121.07(19) . . ?
C15 C14 N1 128.25(18) . . ?
C14 C15 H15 121.1 . . ?
C14 C15 C16 117.8(2) . . ?
C16 C15 H15 121.1 . . ?
C15 C16 H16 119.3 . . ?
C15 C16 C17 121.36(18) . . ?
C17 C16 H16 119.3 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.5(2) . . ?
C18 C17 H17 119.7 . . ?
C13 C18 C17 117.9(2) . . ?
C13 C18 H18 121.0 . . ?
C17 C18 H18 121.0 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
C11 N1 C14 111.68(14) . . ?
C11 N1 C19 123.52(16) . . ?
C14 N1 C19 124.81(15) . . ?
C9 O1 C5 123.44(13) . . ?
C10 O4 C12 110.74(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.7(3) . . . . ?
C1 C6 C7 C8 -179.74(14) . . . . ?
C1 C6 C7 C12 1.5(2) . . . . ?
C2 C1 C6 C5 0.6(2) . . . . ?
C2 C1 C6 C7 179.80(14) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C3 C4 C5 O1 178.41(16) . . . . ?
C4 C5 C6 C1 0.5(2) . . . . ?
C4 C5 C6 C7 -178.77(15) . . . . ?
C4 C5 O1 C9 179.52(16) . . . . ?
C5 C6 C7 C8 -0.5(2) . . . . ?
C5 C6 C7 C12 -179.29(14) . . . . ?
C6 C1 C2 C3 -1.2(2) . . . . ?
C6 C5 O1 C9 -1.0(3) . . . . ?
C6 C7 C8 C9 -1.6(2) . . . . ?
C6 C7 C8 C10 177.45(13) . . . . ?
C6 C7 C12 C11 66.15(18) . . . . ?
C6 C7 C12 C13 -52.0(2) . . . . ?
C6 C7 C12 O4 -177.36(13) . . . . ?
C7 C8 C9 O1 2.3(2) . . . . ?
C7 C8 C9 O2 -176.35(18) . . . . ?
C7 C8 C10 O3 -176.28(17) . . . . ?
C7 C8 C10 O4 1.96(17) . . . . ?
C7 C12 C13 C14 121.79(15) . . . . ?
C7 C12 C13 C18 -56.5(2) . . . . ?
C7 C12 O4 C10 -2.55(15) . . . . ?
C8 C7 C12 C11 -112.75(13) . . . . ?
C8 C7 C12 C13 129.06(14) . . . . ?
C8 C7 C12 O4 3.74(15) . . . . ?
C8 C9 O1 C5 -1.0(2) . . . . ?
C8 C10 O4 C12 0.56(16) . . . . ?
C9 C8 C10 O3 2.7(3) . . . . ?
C9 C8 C10 O4 -179.04(14) . . . . ?
C10 C8 C9 O1 -176.54(14) . . . . ?
C10 C8 C9 O2 4.8(3) . . . . ?
C11 C12 C13 C14 -0.83(15) . . . . ?
C11 C12 C13 C18 -179.13(17) . . . . ?
C11 C12 O4 C10 115.93(13) . . . . ?
C12 C7 C8 C9 177.39(14) . . . . ?
C12 C7 C8 C10 -3.56(17) . . . . ?
C12 C11 N1 C14 -2.27(17) . . . . ?
C12 C11 N1 C19 177.82(15) . . . . ?
C12 C13 C14 C15 -179.58(15) . . . . ?
C12 C13 C14 N1 -0.46(18) . . . . ?
C12 C13 C18 C17 179.14(17) . . . . ?
C13 C12 O4 C10 -130.86(13) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C13 C14 N1 C11 1.81(19) . . . . ?
C13 C14 N1 C19 -178.28(16) . . . . ?
C14 C13 C18 C17 1.0(3) . . . . ?
C14 C15 C16 C17 1.2(3) . . . . ?
C15 C14 N1 C11 -179.14(17) . . . . ?
C15 C14 N1 C19 0.8(3) . . . . ?
C15 C16 C17 C18 -1.2(3) . . . . ?
C16 C17 C18 C13 0.1(3) . . . . ?
C18 C13 C14 C15 -1.1(3) . . . . ?
C18 C13 C14 N1 178.04(15) . . . . ?
N1 C11 C12 C7 -124.84(13) . . . . ?
N1 C11 C12 C13 1.87(15) . . . . ?
N1 C11 C12 O4 121.46(13) . . . . ?
N1 C14 C15 C16 -179.00(18) . . . . ?
O1 C5 C6 C1 -178.89(14) . . . . ?
O1 C5 C6 C7 1.8(2) . . . . ?
O2 C9 O1 C5 177.79(17) . . . . ?
O3 C10 O4 C12 179.01(14) . . . . ?
O4 C12 C13 C14 -117.39(14) . . . . ?
O4 C12 C13 C18 64.3(2) . . . . ?
O5 C11 C12 C7 54.3(2) . . . . ?
O5 C11 C12 C13 -178.99(15) . . . . ?
O5 C11 C12 O4 -59.39(19) . . . . ?
O5 C11 N1 C14 178.63(16) . . . . ?
O5 C11 N1 C19 -1.3(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
