# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

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

data_20190494
_database_code_depnum_ccdc_archive 'CCDC 1911493'
loop_
_audit_author_name
_audit_author_address
'wang yue'
;Zhengzhou University
China
;
_audit_update_record             
;
2019-04-22 deposited with the CCDC.	2021-04-12 downloaded from the CCDC.
;
_audit_creation_date             2019-04-17
_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         'C24 H22 N2 O8'
_chemical_formula_sum            'C24 H22 N2 O8'
_chemical_formula_weight         466.43
_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      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                   13.6988(3)
_cell_length_b                   13.6615(2)
_cell_length_c                   14.5332(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.162(2)
_cell_angle_gamma                90
_cell_volume                     2625.17(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3622
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7290
_cell_measurement_theta_min      4.4970
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.895
_exptl_absorpt_coefficient_mu    0.754
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79178
_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    1.180
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10184
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.083
_diffrn_reflns_theta_max         67.083
_diffrn_reflns_theta_min         3.949
_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  -32.00   -7.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000    0.0000 50

#__ type_ start__ end____ width___ exp.time_
  2 omega -103.00  -56.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000    0.0000 94

#__ type_ start__ end____ width___ exp.time_
  3 omega -107.00  -82.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -120.0000 50

#__ type_ start__ end____ width___ exp.time_
  4 omega  -56.00  -20.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000  120.0000 72

#__ type_ start__ end____ width___ exp.time_
  5 omega  -99.00  -22.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000 -120.0000 154

#__ type_ start__ end____ width___ exp.time_
  6 omega   64.00  108.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  120.0000 88

#__ type_ start__ end____ width___ exp.time_
  7 omega   -1.00   59.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000 -150.0000 120

#__ type_ start__ end____ width___ exp.time_
  8 omega   83.00  109.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 52

#__ type_ start__ end____ width___ exp.time_
  9 omega    5.00   69.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000   90.0000 128

#__ type_ start__ end____ width___ exp.time_
 10 omega   84.00  109.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   19.0000   90.0000 50

#__ type_ start__ end____ width___ exp.time_
 11 omega   58.00  105.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -30.0000 94

#__ type_ start__ end____ width___ exp.time_
 12 omega   28.00   67.00   0.5000    1.2500
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  120.0000 78

#__ type_ start__ end____ width___ exp.time_
 13 omega   41.00   99.00   0.5000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 116

#__ type_ start__ end____ width___ exp.time_
 14 omega   52.00   99.00   0.5000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 94

#__ type_ start__ end____ width___ exp.time_
 15 omega   44.00   86.00   0.5000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
 16 omega   49.00   95.00   0.5000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 92

#__ type_ start__ end____ width___ exp.time_
 17 omega   39.00   91.00   0.5000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 104

#__ type_ start__ end____ width___ exp.time_
 18 omega   88.00  174.00   0.5000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -60.0000 172

#__ type_ start__ end____ width___ exp.time_
 19 omega   41.00   94.00   0.5000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 106

#__ type_ start__ end____ width___ exp.time_
 20 omega   58.00   96.00   0.5000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 76

#__ type_ start__ end____ width___ exp.time_
 21 omega   42.00   76.00   0.5000   22.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -180.0000 68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0907119000
_diffrn_orient_matrix_UB_12      -0.0177630000
_diffrn_orient_matrix_UB_13      0.0420575000
_diffrn_orient_matrix_UB_21      -0.0680285000
_diffrn_orient_matrix_UB_22      -0.0197448000
_diffrn_orient_matrix_UB_23      -0.1008199000
_diffrn_orient_matrix_UB_31      0.0269816000
_diffrn_orient_matrix_UB_32      -0.1095308000
_diffrn_orient_matrix_UB_33      0.0112798000
_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                3720
_reflns_number_total             4697
_reflns_odcompleteness_completeness 99.84
_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         0.204
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4697
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0510
_refine_ls_restrained_S_all      1.062
_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)+(0.0871P)²+0.2346P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1473
_refine_ls_wR_factor_ref         0.1596
_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
2. Restrained distances
 C21A-C20A
 1.53 with sigma of 0.02
 C20-C21
 1.53 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C21) = Uanis(C21A)
Uanis(C20) = Uanis(C20A)
4. Others
 Sof(C20A)=Sof(H20C)=Sof(H20D)=Sof(C21A)=Sof(H21D)=Sof(H21E)=Sof(H21F)=1-FVAR(1)
 Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C7(H7)
5.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C20(H20A,H20B), C20A(H20C,H20D), C23(H23A,H23B)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C10(H10), C14(H14), C15(H15), C17(H17),
 C18(H18)
5.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C21A(H21D,H21E,H21F), C24(H24A,H24B,H24C)
;
_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 0.40565(14) 0.47798(12) 0.33856(13) 0.0502(4) Uani 1 1 d . . . . .
H1 H 0.3694 0.4226 0.3124 0.060 Uiso 1 1 calc R . . . .
C2 C 0.50984(15) 0.47276(14) 0.37254(14) 0.0543(4) Uani 1 1 d . . . . .
H2 H 0.5439 0.4146 0.3689 0.065 Uiso 1 1 calc R . . . .
C3 C 0.56200(14) 0.55525(15) 0.41177(13) 0.0534(4) Uani 1 1 d . . . . .
C4 C 0.51420(15) 0.64300(14) 0.41654(15) 0.0595(5) Uani 1 1 d . . . . .
H4 H 0.5511 0.6979 0.4431 0.071 Uiso 1 1 calc R . . . .
C5 C 0.41022(15) 0.64793(13) 0.38105(14) 0.0562(4) Uani 1 1 d . . . . .
H5 H 0.3771 0.7071 0.3825 0.067 Uiso 1 1 calc R . . . .
C6 C 0.35475(13) 0.56515(12) 0.34312(12) 0.0462(4) Uani 1 1 d . . . . .
C7 C 0.24179(13) 0.56844(12) 0.31580(12) 0.0467(4) Uani 1 1 d . . . . .
H7 H 0.2129 0.5579 0.3700 0.056 Uiso 1 1 calc R . . . .
C8 C 0.18107(14) 0.64030(12) 0.24332(13) 0.0504(4) Uani 1 1 d . . . . .
C9 C 0.23010(16) 0.68723(13) 0.17243(15) 0.0582(5) Uani 1 1 d . . . . .
H9A H 0.1834 0.7313 0.1304 0.070 Uiso 1 1 calc R . . . .
H9B H 0.2900 0.7236 0.2049 0.070 Uiso 1 1 calc R . . . .
C10 C 0.25718(15) 0.60330(14) 0.11770(13) 0.0567(4) Uani 1 1 d . . . . .
H10 H 0.2913 0.6102 0.0706 0.068 Uiso 1 1 calc R . . . .
C11 C 0.22687(14) 0.51781(13) 0.14411(12) 0.0492(4) Uani 1 1 d . . . . .
C12 C 0.17689(13) 0.52748(11) 0.22395(12) 0.0463(4) Uani 1 1 d . . . . .
C13 C 0.08545(13) 0.46740(12) 0.22102(13) 0.0472(4) Uani 1 1 d . . . . .
C14 C 0.08046(15) 0.40266(15) 0.29285(14) 0.0589(5) Uani 1 1 d . . . . .
H14 H 0.1349 0.3979 0.3466 0.071 Uiso 1 1 calc R . . . .
C15 C -0.00373(18) 0.34509(17) 0.28625(17) 0.0700(6) Uani 1 1 d . . . . .
H15 H -0.0061 0.3009 0.3343 0.084 Uiso 1 1 calc R . . . .
C16 C -0.08440(16) 0.35445(17) 0.20694(18) 0.0668(5) Uani 1 1 d . . . . .
C17 C -0.08312(17) 0.41864(19) 0.13507(18) 0.0742(6) Uani 1 1 d . . . . .
H17 H -0.1387 0.4247 0.0826 0.089 Uiso 1 1 calc R . . . .
C18 C 0.00264(16) 0.47416(16) 0.14233(15) 0.0640(5) Uani 1 1 d . . . . .
H18 H 0.0050 0.5171 0.0933 0.077 Uiso 1 1 calc R . . . .
C19 C 0.09099(14) 0.68900(13) 0.26192(15) 0.0573(5) Uani 1 1 d . . . . .
C20 C -0.0299(9) 0.6820(6) 0.3516(7) 0.0806(18) Uani 0.744(10) 1 d D . P A 1
H20A H -0.0857 0.6649 0.2976 0.097 Uiso 0.744(10) 1 calc R . P A 1
H20B H -0.0295 0.7525 0.3596 0.097 Uiso 0.744(10) 1 calc R . P A 1
C20A C -0.026(3) 0.697(2) 0.369(3) 0.0806(18) Uani 0.256(10) 1 d D . P A 2
H20C H -0.0029 0.7288 0.4303 0.097 Uiso 0.256(10) 1 calc R . P A 2
H20D H -0.0656 0.7419 0.3226 0.097 Uiso 0.256(10) 1 calc R . P A 2
C21 C -0.0424(5) 0.6336(6) 0.4382(6) 0.137(3) Uani 0.744(10) 1 d D . P A 1
H21A H -0.0684 0.5688 0.4227 0.205 Uiso 0.744(10) 1 calc GR . P A 1
H21B H -0.0887 0.6706 0.4638 0.205 Uiso 0.744(10) 1 calc GR . P A 1
H21C H 0.0219 0.6300 0.4845 0.205 Uiso 0.744(10) 1 calc GR . P A 1
C21A C -0.0832(15) 0.6033(17) 0.3754(18) 0.137(3) Uani 0.256(10) 1 d D . P A 2
H21D H -0.1155 0.5803 0.3124 0.205 Uiso 0.256(10) 1 calc GR . P A 2
H21E H -0.1334 0.6158 0.4092 0.205 Uiso 0.256(10) 1 calc GR . P A 2
H21F H -0.0369 0.5544 0.4087 0.205 Uiso 0.256(10) 1 calc GR . P A 2
C22 C 0.24353(14) 0.41961(13) 0.10837(13) 0.0518(4) Uani 1 1 d . . . . .
C23 C 0.2824(2) 0.3277(2) -0.0163(2) 0.0811(7) Uani 1 1 d . . . . .
H23A H 0.3069 0.2801 0.0340 0.097 Uiso 1 1 calc R . . . .
H23B H 0.3326 0.3341 -0.0522 0.097 Uiso 1 1 calc R . . . .
C24 C 0.1858(3) 0.2938(3) -0.0798(3) 0.1066(10) Uani 1 1 d . . . . .
H24A H 0.1604 0.3423 -0.1279 0.160 Uiso 1 1 calc GR . . . .
H24B H 0.1376 0.2836 -0.0432 0.160 Uiso 1 1 calc GR . . . .
H24C H 0.1964 0.2334 -0.1096 0.160 Uiso 1 1 calc GR . . . .
N1 N 0.67176(14) 0.54929(16) 0.45275(14) 0.0682(5) Uani 1 1 d . . . . .
N2 N -0.1744(2) 0.2928(2) 0.1987(2) 0.0999(8) Uani 1 1 d . . . . .
O1 O 0.71514(14) 0.47456(17) 0.44173(18) 0.0965(6) Uani 1 1 d . . . . .
O2 O 0.71456(13) 0.61796(17) 0.49918(15) 0.0932(6) Uani 1 1 d . . . . .
O3 O -0.2442(2) 0.3024(3) 0.1286(3) 0.1609(15) Uani 1 1 d . . . . .
O4 O -0.1734(3) 0.2336(3) 0.2595(3) 0.1730(17) Uani 1 1 d . . . . .
O5 O 0.04646(13) 0.75457(12) 0.21311(17) 0.0877(6) Uani 1 1 d . . . . .
O6 O 0.06384(12) 0.65054(12) 0.33473(12) 0.0688(4) Uani 1 1 d . . . . .
O7 O 0.23658(13) 0.34540(10) 0.15055(11) 0.0681(4) Uani 1 1 d . . . . .
O8 O 0.26747(15) 0.42234(12) 0.02540(11) 0.0732(4) 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 1.385(3) . ?
C1 C6 1.390(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(3) . ?
C3 C4 1.376(3) . ?
C3 N1 1.468(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.393(2) . ?
C6 C7 1.494(2) . ?
C7 H7 0.9800 . ?
C7 C8 1.519(2) . ?
C7 C12 1.505(2) . ?
C8 C9 1.512(3) . ?
C8 C12 1.565(2) . ?
C8 C19 1.488(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.496(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.329(3) . ?
C11 C12 1.499(3) . ?
C11 C22 1.478(3) . ?
C12 C13 1.489(2) . ?
C13 C14 1.383(3) . ?
C13 C18 1.387(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.378(3) . ?
C16 C17 1.367(4) . ?
C16 N2 1.473(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(3) . ?
C18 H18 0.9300 . ?
C19 O5 1.205(2) . ?
C19 O6 1.319(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.470(10) . ?
C20 O6 1.435(11) . ?
C20A H20C 0.9700 . ?
C20A H20D 0.9700 . ?
C20A C21A 1.511(19) . ?
C20A O6 1.57(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C21A H21D 0.9600 . ?
C21A H21E 0.9600 . ?
C21A H21F 0.9600 . ?
C22 O7 1.201(2) . ?
C22 O8 1.330(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.477(4) . ?
C23 O8 1.465(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
N1 O1 1.213(3) . ?
N1 O2 1.213(3) . ?
N2 O3 1.208(4) . ?
N2 O4 1.194(4) . ?

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 119.7 . . ?
C2 C1 C6 120.68(16) . . ?
C6 C1 H1 119.7 . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.74(17) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C4 122.14(17) . . ?
C2 C3 N1 119.25(18) . . ?
C4 C3 N1 118.58(18) . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.72(17) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.64(17) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 119.05(16) . . ?
C1 C6 C7 120.70(15) . . ?
C5 C6 C7 120.03(16) . . ?
C6 C7 H7 112.9 . . ?
C6 C7 C8 123.02(15) . . ?
C6 C7 C12 123.71(16) . . ?
C8 C7 H7 112.9 . . ?
C12 C7 H7 112.9 . . ?
C12 C7 C8 62.34(11) . . ?
C7 C8 C12 58.40(10) . . ?
C9 C8 C7 119.10(16) . . ?
C9 C8 C12 107.27(16) . . ?
C19 C8 C7 119.53(17) . . ?
C19 C8 C9 118.14(16) . . ?
C19 C8 C12 118.69(16) . . ?
C8 C9 H9A 110.8 . . ?
C8 C9 H9B 110.8 . . ?
H9A C9 H9B 108.9 . . ?
C10 C9 C8 104.68(14) . . ?
C10 C9 H9A 110.8 . . ?
C10 C9 H9B 110.8 . . ?
C9 C10 H10 123.8 . . ?
C11 C10 C9 112.34(18) . . ?
C11 C10 H10 123.8 . . ?
C10 C11 C12 112.73(17) . . ?
C10 C11 C22 127.41(18) . . ?
C22 C11 C12 119.72(15) . . ?
C7 C12 C8 59.26(11) . . ?
C11 C12 C7 115.84(15) . . ?
C11 C12 C8 102.91(15) . . ?
C13 C12 C7 121.85(16) . . ?
C13 C12 C8 122.61(16) . . ?
C13 C12 C11 118.71(15) . . ?
C14 C13 C12 122.56(16) . . ?
C14 C13 C18 118.26(17) . . ?
C18 C13 C12 119.16(16) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 C13 121.18(19) . . ?
C15 C14 H14 119.4 . . ?
C14 C15 H15 120.7 . . ?
C16 C15 C14 118.6(2) . . ?
C16 C15 H15 120.7 . . ?
C15 C16 N2 119.1(2) . . ?
C17 C16 C15 122.0(2) . . ?
C17 C16 N2 118.9(2) . . ?
C16 C17 H17 120.8 . . ?
C16 C17 C18 118.4(2) . . ?
C18 C17 H17 120.8 . . ?
C13 C18 H18 119.2 . . ?
C17 C18 C13 121.5(2) . . ?
C17 C18 H18 119.2 . . ?
O5 C19 C8 122.8(2) . . ?
O5 C19 O6 124.3(2) . . ?
O6 C19 C8 112.89(15) . . ?
H20A C20 H20B 108.3 . . ?
C21 C20 H20A 109.9 . . ?
C21 C20 H20B 109.9 . . ?
O6 C20 H20A 109.9 . . ?
O6 C20 H20B 109.9 . . ?
O6 C20 C21 108.7(8) . . ?
H20C C20A H20D 109.8 . . ?
C21A C20A H20C 112.1 . . ?
C21A C20A H20D 112.1 . . ?
C21A C20A O6 98.2(18) . . ?
O6 C20A H20C 112.1 . . ?
O6 C20A H20D 112.1 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20A C21A H21D 109.5 . . ?
C20A C21A H21E 109.5 . . ?
C20A C21A H21F 109.5 . . ?
H21D C21A H21E 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?
O7 C22 C11 123.14(18) . . ?
O7 C22 O8 123.87(18) . . ?
O8 C22 C11 112.98(16) . . ?
H23A C23 H23B 108.2 . . ?
C24 C23 H23A 109.8 . . ?
C24 C23 H23B 109.8 . . ?
O8 C23 H23A 109.8 . . ?
O8 C23 H23B 109.8 . . ?
O8 C23 C24 109.6(3) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O1 N1 C3 118.6(2) . . ?
O1 N1 O2 122.8(2) . . ?
O2 N1 C3 118.5(2) . . ?
O3 N2 C16 117.9(3) . . ?
O4 N2 C16 118.6(3) . . ?
O4 N2 O3 123.4(3) . . ?
C19 O6 C20 118.1(4) . . ?
C19 O6 C20A 120.2(13) . . ?
C22 O8 C23 116.39(18) . . ?

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 -1.3(3) . . . . ?
C1 C2 C3 N1 176.69(17) . . . . ?
C1 C6 C7 C8 -126.90(18) . . . . ?
C1 C6 C7 C12 -50.3(2) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C2 C1 C6 C7 -173.68(17) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C2 C3 N1 O1 7.9(3) . . . . ?
C2 C3 N1 O2 -169.4(2) . . . . ?
C3 C4 C5 C6 1.4(3) . . . . ?
C4 C3 N1 O1 -174.1(2) . . . . ?
C4 C3 N1 O2 8.7(3) . . . . ?
C4 C5 C6 C1 -2.0(3) . . . . ?
C4 C5 C6 C7 172.70(19) . . . . ?
C5 C6 C7 C8 58.5(2) . . . . ?
C5 C6 C7 C12 135.04(18) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C6 C7 C8 C9 20.8(2) . . . . ?
C6 C7 C8 C12 113.99(19) . . . . ?
C6 C7 C8 C19 -138.59(17) . . . . ?
C6 C7 C12 C8 -112.96(19) . . . . ?
C6 C7 C12 C11 -22.9(2) . . . . ?
C6 C7 C12 C13 135.41(18) . . . . ?
C7 C8 C9 C10 60.5(2) . . . . ?
C7 C8 C12 C11 -112.58(15) . . . . ?
C7 C8 C12 C13 110.40(19) . . . . ?
C7 C8 C19 O5 171.36(18) . . . . ?
C7 C8 C19 O6 -10.8(2) . . . . ?
C7 C12 C13 C14 -35.7(3) . . . . ?
C7 C12 C13 C18 146.05(19) . . . . ?
C8 C7 C12 C11 90.05(16) . . . . ?
C8 C7 C12 C13 -111.63(19) . . . . ?
C8 C9 C10 C11 2.8(2) . . . . ?
C8 C12 C13 C14 -107.2(2) . . . . ?
C8 C12 C13 C18 74.5(2) . . . . ?
C8 C19 O6 C20 -171.5(4) . . . . ?
C8 C19 O6 C20A 176.4(14) . . . . ?
C9 C8 C12 C7 114.00(16) . . . . ?
C9 C8 C12 C11 1.42(17) . . . . ?
C9 C8 C12 C13 -135.61(17) . . . . ?
C9 C8 C19 O5 11.8(3) . . . . ?
C9 C8 C19 O6 -170.36(16) . . . . ?
C9 C10 C11 C12 -2.0(2) . . . . ?
C9 C10 C11 C22 -177.63(17) . . . . ?
C10 C11 C12 C7 -61.5(2) . . . . ?
C10 C11 C12 C8 0.33(19) . . . . ?
C10 C11 C12 C13 139.43(16) . . . . ?
C10 C11 C22 O7 161.1(2) . . . . ?
C10 C11 C22 O8 -18.6(3) . . . . ?
C11 C12 C13 C14 122.0(2) . . . . ?
C11 C12 C13 C18 -56.2(2) . . . . ?
C11 C22 O8 C23 -178.33(19) . . . . ?
C12 C7 C8 C9 -93.24(18) . . . . ?
C12 C7 C8 C19 107.42(18) . . . . ?
C12 C8 C9 C10 -2.47(18) . . . . ?
C12 C8 C19 O5 -120.8(2) . . . . ?
C12 C8 C19 O6 57.1(2) . . . . ?
C12 C11 C22 O7 -14.3(3) . . . . ?
C12 C11 C22 O8 166.10(16) . . . . ?
C12 C13 C14 C15 -177.3(2) . . . . ?
C12 C13 C18 C17 178.6(2) . . . . ?
C13 C14 C15 C16 -1.2(4) . . . . ?
C14 C13 C18 C17 0.3(3) . . . . ?
C14 C15 C16 C17 0.1(4) . . . . ?
C14 C15 C16 N2 179.5(2) . . . . ?
C15 C16 C17 C18 1.1(4) . . . . ?
C15 C16 N2 O3 179.9(3) . . . . ?
C15 C16 N2 O4 -2.8(5) . . . . ?
C16 C17 C18 C13 -1.3(4) . . . . ?
C17 C16 N2 O3 -0.7(5) . . . . ?
C17 C16 N2 O4 176.6(4) . . . . ?
C18 C13 C14 C15 1.0(3) . . . . ?
C19 C8 C9 C10 -139.91(16) . . . . ?
C19 C8 C12 C7 -108.84(19) . . . . ?
C19 C8 C12 C11 138.58(17) . . . . ?
C19 C8 C12 C13 1.6(3) . . . . ?
C21 C20 O6 C19 -177.3(6) . . . . ?
C21A C20A O6 C19 132.0(18) . . . . ?
C22 C11 C12 C7 114.45(17) . . . . ?
C22 C11 C12 C8 176.31(15) . . . . ?
C22 C11 C12 C13 -44.6(2) . . . . ?
C24 C23 O8 C22 91.0(3) . . . . ?
N1 C3 C4 C5 -177.70(19) . . . . ?
N2 C16 C17 C18 -178.3(3) . . . . ?
O5 C19 O6 C20 6.3(5) . . . . ?
O5 C19 O6 C20A -5.8(14) . . . . ?
O7 C22 O8 C23 2.1(3) . . . . ?

_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 0.000 0.000 0.500 198.3 51.3 ?
2 0.500 0.500 0.000 198.3 51.3 ?


_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_201906169
_database_code_depnum_ccdc_archive 'CCDC 1937397'
loop_
_audit_author_name
_audit_author_address
zd
;ZZU
China
;
_audit_update_record             
;
2019-07-01 deposited with the CCDC.	2021-04-12 downloaded from the CCDC.
;
_audit_creation_date             2019-06-27
_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         'C23 H19 Br N O6'
_chemical_formula_sum            'C23 H19 Br N O6'
_chemical_formula_weight         485.30
_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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   10.831(8)
_cell_length_b                   9.562(7)
_cell_length_c                   21.288(15)
_cell_angle_alpha                90
_cell_angle_beta                 99.15(6)
_cell_angle_gamma                90
_cell_volume                     2177(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3535
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.5780
_cell_measurement_theta_min      4.3210
_shelx_estimated_absorpt_T_max   0.759
_shelx_estimated_absorpt_T_min   0.607
_exptl_absorpt_coefficient_mu    2.918
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             988
_exptl_crystal_size_max          0.19
_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  0.0639
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9143
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.303
_diffrn_reflns_theta_max         67.303
_diffrn_reflns_theta_min         4.207
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -86.00  -41.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -30.0000 45

#__ type_ start__ end____ width___ exp.time_
  2 omega  -61.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000  -30.0000 43

#__ type_ start__ end____ width___ exp.time_
  3 omega -101.00  -22.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000 -150.0000 79

#__ type_ start__ end____ width___ exp.time_
  4 omega   61.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000 -180.0000 35

#__ type_ start__ end____ width___ exp.time_
  5 omega   22.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -180.0000 73

#__ type_ start__ end____ width___ exp.time_
  6 omega   -1.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -60.0000 31

#__ type_ start__ end____ width___ exp.time_
  7 omega    8.00   34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega  -31.00   -6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega   24.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -150.0000 31

#__ type_ start__ end____ width___ exp.time_
 10 omega   -4.00   22.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   34.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  -60.0000 32

#__ type_ start__ end____ width___ exp.time_
 12 omega   80.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega   48.00  115.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 67

#__ type_ start__ end____ width___ exp.time_
 14 omega   73.00  103.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 30

#__ type_ start__ end____ width___ exp.time_
 15 omega   50.00   76.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   40.00   66.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   43.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 18 omega   69.00  172.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000 -180.0000 103

#__ type_ start__ end____ width___ exp.time_
 19 omega   42.00   91.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 49

#__ type_ start__ end____ width___ exp.time_
 20 omega   43.00   79.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 36

#__ type_ start__ end____ width___ exp.time_
 21 omega   38.00   64.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 22 omega   63.00  127.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  120.0000 64

#__ type_ start__ end____ width___ exp.time_
 23 omega   57.00   82.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 24 omega   32.00   58.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega   59.00   85.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 26 omega  103.00  128.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 27 omega  126.00  152.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -90.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1110239000
_diffrn_orient_matrix_UB_12      -0.0378722000
_diffrn_orient_matrix_UB_13      0.0337597000
_diffrn_orient_matrix_UB_21      -0.0908163000
_diffrn_orient_matrix_UB_22      0.0684252000
_diffrn_orient_matrix_UB_23      -0.0543843000
_diffrn_orient_matrix_UB_31      -0.0142317000
_diffrn_orient_matrix_UB_32      -0.1410193000
_diffrn_orient_matrix_UB_33      -0.0354091000
_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                3289
_reflns_number_total             3875
_reflns_odcompleteness_completeness 99.40
_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         0.548
_refine_diff_density_min         -0.701
_refine_diff_density_rms         0.096
_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     282
_refine_ls_number_reflns         3875
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0570
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1017P)²+0.2931P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1506
_refine_ls_wR_factor_ref         0.1635
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C11(H11), C12(H12), C17(H17), C18(H18),
 C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.66474(5) 0.79317(5) 0.33805(2) 0.0832(2) Uani 1 1 d . . . . .
C1 C 0.8051(3) 0.4657(3) 0.45340(13) 0.0461(6) Uani 1 1 d . . . . .
H1 H 0.8240 0.3720 0.4479 0.055 Uiso 1 1 calc R . . . .
C2 C 0.7623(3) 0.5465(3) 0.40094(14) 0.0503(6) Uani 1 1 d . . . . .
H2 H 0.7527 0.5083 0.3603 0.060 Uiso 1 1 calc R . . . .
C3 C 0.7339(3) 0.6859(3) 0.40981(14) 0.0490(6) Uani 1 1 d . . . . .
C4 C 0.7522(3) 0.7457(3) 0.46906(15) 0.0484(6) Uani 1 1 d . . . . .
H4 H 0.7355 0.8401 0.4740 0.058 Uiso 1 1 calc R . . . .
C5 C 0.7958(2) 0.6635(3) 0.52154(14) 0.0445(6) Uani 1 1 d . . . . .
H5 H 0.8086 0.7034 0.5619 0.053 Uiso 1 1 calc R . . . .
C6 C 0.8207(2) 0.5213(3) 0.51456(12) 0.0385(5) Uani 1 1 d . . . . .
C7 C 0.8646(2) 0.4303(2) 0.57031(12) 0.0375(5) Uani 1 1 d . . . . .
H7 H 0.9558 0.4246 0.5814 0.045 Uiso 1 1 calc R . . . .
C8 C 0.7960(2) 0.4216(3) 0.62736(12) 0.0410(5) Uani 1 1 d . . . . .
C9 C 0.7975(2) 0.2956(2) 0.58117(12) 0.0362(5) Uani 1 1 d . . . . .
C10 C 0.6648(2) 0.2885(3) 0.54775(13) 0.0398(5) Uani 1 1 d . . . . .
C11 C 0.5924(2) 0.3852(3) 0.56823(15) 0.0480(6) Uani 1 1 d . . . . .
H11 H 0.5083 0.3973 0.5517 0.058 Uiso 1 1 calc R . . . .
C12 C 0.6608(3) 0.4720(3) 0.62046(15) 0.0511(6) Uani 1 1 d . . . . .
H12 H 0.6284 0.5414 0.6437 0.061 Uiso 1 1 calc R . . . .
C13 C 0.8697(3) 0.4135(3) 0.69228(13) 0.0477(6) Uani 1 1 d . . . . .
C14 C 1.0666(3) 0.3579(4) 0.75309(15) 0.0612(8) Uani 1 1 d . . . . .
H14A H 1.0420 0.4237 0.7835 0.073 Uiso 1 1 calc R . . . .
H14B H 1.1528 0.3768 0.7488 0.073 Uiso 1 1 calc R . . . .
C15 C 1.0554(5) 0.2110(4) 0.7769(2) 0.0804(11) Uani 1 1 d . . . . .
H15A H 1.0807 0.1462 0.7469 0.121 Uiso 1 1 calc GR . . . .
H15B H 0.9702 0.1929 0.7816 0.121 Uiso 1 1 calc GR . . . .
H15C H 1.1084 0.2002 0.8172 0.121 Uiso 1 1 calc GR . . . .
C16 C 0.8639(2) 0.1624(3) 0.60169(12) 0.0367(5) Uani 1 1 d . . . . .
C17 C 0.9704(2) 0.1210(3) 0.57815(14) 0.0471(6) Uani 1 1 d . . . . .
H17 H 1.0018 0.1768 0.5486 0.057 Uiso 1 1 calc R . . . .
C18 C 1.0306(3) -0.0032(3) 0.59842(15) 0.0521(7) Uani 1 1 d . . . . .
H18 H 1.1031 -0.0303 0.5835 0.063 Uiso 1 1 calc R . . . .
C19 C 0.9802(3) -0.0853(3) 0.64133(13) 0.0464(6) Uani 1 1 d . . . . .
C20 C 0.8739(3) -0.0484(3) 0.66507(13) 0.0465(6) Uani 1 1 d . . . . .
H20 H 0.8414 -0.1061 0.6936 0.056 Uiso 1 1 calc R . . . .
C21 C 0.8164(2) 0.0770(3) 0.64519(13) 0.0417(5) Uani 1 1 d . . . . .
H21 H 0.7451 0.1045 0.6611 0.050 Uiso 1 1 calc R . . . .
C22 C 0.6297(2) 0.1902(3) 0.49464(13) 0.0433(6) Uani 1 1 d . . . . .
C23 C 0.4633(4) 0.1066(5) 0.41917(18) 0.0733(10) Uani 1 1 d . . . . .
H23A H 0.4822 0.1452 0.3802 0.110 Uiso 1 1 calc GR . . . .
H23B H 0.3745 0.0957 0.4162 0.110 Uiso 1 1 calc GR . . . .
H23C H 0.5031 0.0170 0.4266 0.110 Uiso 1 1 calc GR . . . .
N1 N 1.0440(3) -0.2163(3) 0.66340(14) 0.0621(7) Uani 1 1 d . . . . .
O1 O 0.8259(3) 0.4360(3) 0.73973(11) 0.0723(7) Uani 1 1 d . . . . .
O2 O 0.98740(19) 0.3760(2) 0.69205(9) 0.0508(5) Uani 1 1 d . . . . .
O3 O 1.1498(3) -0.2349(4) 0.65445(18) 0.0990(11) Uani 1 1 d . . . . .
O4 O 0.9858(4) -0.2996(3) 0.6917(2) 0.1019(12) Uani 1 1 d . . . . .
O5 O 0.7010(2) 0.1129(3) 0.47446(12) 0.0639(6) Uani 1 1 d . . . . .
O6 O 0.5082(2) 0.1983(3) 0.47059(13) 0.0639(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.893(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.376(4) . ?
C1 C6 1.392(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(5) . ?
C3 C4 1.370(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.399(4) . ?
C6 C7 1.488(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.523(3) . ?
C7 C9 1.515(3) . ?
C8 C9 1.557(3) . ?
C8 C12 1.527(4) . ?
C8 C13 1.484(4) . ?
C9 C10 1.500(4) . ?
C9 C16 1.493(3) . ?
C10 C11 1.331(4) . ?
C10 C22 1.473(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.487(5) . ?
C12 H12 0.9300 . ?
C13 O1 1.202(4) . ?
C13 O2 1.325(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.504(5) . ?
C14 O2 1.449(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.386(4) . ?
C16 C21 1.393(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.390(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(5) . ?
C19 C20 1.375(4) . ?
C19 N1 1.471(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.386(4) . ?
C21 H21 0.9300 . ?
C22 O5 1.197(4) . ?
C22 O6 1.336(4) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C23 O6 1.427(4) . ?
N1 O3 1.205(5) . ?
N1 O4 1.231(5) . ?

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 119.3 . . ?
C2 C1 C6 121.3(3) . . ?
C6 C1 H1 119.3 . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.8(3) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 Br1 118.6(2) . . ?
C4 C3 Br1 119.8(2) . . ?
C4 C3 C2 121.6(3) . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.1(3) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.3(3) . . ?
C1 C6 C7 119.9(2) . . ?
C5 C6 C7 121.8(2) . . ?
C6 C7 H7 114.0 . . ?
C6 C7 C8 122.2(2) . . ?
C6 C7 C9 121.3(2) . . ?
C8 C7 H7 114.0 . . ?
C9 C7 H7 114.0 . . ?
C9 C7 C8 61.65(16) . . ?
C7 C8 C9 58.90(15) . . ?
C7 C8 C12 119.2(2) . . ?
C12 C8 C9 106.8(2) . . ?
C13 C8 C7 119.2(2) . . ?
C13 C8 C9 119.4(2) . . ?
C13 C8 C12 118.1(2) . . ?
C7 C9 C8 59.45(16) . . ?
C10 C9 C7 114.4(2) . . ?
C10 C9 C8 103.27(19) . . ?
C16 C9 C7 123.3(2) . . ?
C16 C9 C8 121.9(2) . . ?
C16 C9 C10 118.7(2) . . ?
C11 C10 C9 112.5(2) . . ?
C11 C10 C22 127.0(2) . . ?
C22 C10 C9 120.3(2) . . ?
C10 C11 H11 123.7 . . ?
C10 C11 C12 112.6(2) . . ?
C12 C11 H11 123.7 . . ?
C8 C12 H12 127.7 . . ?
C11 C12 C8 104.6(2) . . ?
C11 C12 H12 127.7 . . ?
O1 C13 C8 123.2(3) . . ?
O1 C13 O2 124.1(3) . . ?
O2 C13 C8 112.7(2) . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
O2 C14 H14A 109.6 . . ?
O2 C14 H14B 109.6 . . ?
O2 C14 C15 110.2(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C9 121.8(2) . . ?
C17 C16 C21 119.3(2) . . ?
C21 C16 C9 118.9(2) . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.5(3) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.8 . . ?
C19 C18 C17 118.4(2) . . ?
C19 C18 H18 120.8 . . ?
C18 C19 N1 118.7(3) . . ?
C20 C19 C18 122.7(3) . . ?
C20 C19 N1 118.6(3) . . ?
C19 C20 H20 121.0 . . ?
C19 C20 C21 118.1(2) . . ?
C21 C20 H20 121.0 . . ?
C16 C21 H21 119.5 . . ?
C20 C21 C16 121.0(2) . . ?
C20 C21 H21 119.5 . . ?
O5 C22 C10 124.5(2) . . ?
O5 C22 O6 123.4(3) . . ?
O6 C22 C10 112.0(2) . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O6 C23 H23A 109.5 . . ?
O6 C23 H23B 109.5 . . ?
O6 C23 H23C 109.5 . . ?
O3 N1 C19 119.1(3) . . ?
O3 N1 O4 123.7(3) . . ?
O4 N1 C19 117.2(3) . . ?
C13 O2 C14 117.5(2) . . ?
C22 O6 C23 116.9(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C3 C4 C5 176.1(2) . . . . ?
C1 C2 C3 Br1 -175.9(2) . . . . ?
C1 C2 C3 C4 2.6(4) . . . . ?
C1 C6 C7 C8 -128.6(3) . . . . ?
C1 C6 C7 C9 -54.5(3) . . . . ?
C2 C1 C6 C5 -2.2(4) . . . . ?
C2 C1 C6 C7 178.7(2) . . . . ?
C2 C3 C4 C5 -2.4(4) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C4 C5 C6 C1 2.4(4) . . . . ?
C4 C5 C6 C7 -178.5(2) . . . . ?
C5 C6 C7 C8 52.4(3) . . . . ?
C5 C6 C7 C9 126.4(3) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
C6 C7 C8 C9 110.9(3) . . . . ?
C6 C7 C8 C12 18.0(4) . . . . ?
C6 C7 C8 C13 -140.5(2) . . . . ?
C6 C7 C9 C8 -112.4(3) . . . . ?
C6 C7 C9 C10 -21.0(3) . . . . ?
C6 C7 C9 C16 137.4(3) . . . . ?
C7 C8 C9 C10 -110.7(2) . . . . ?
C7 C8 C9 C16 112.6(2) . . . . ?
C7 C8 C12 C11 58.5(3) . . . . ?
C7 C8 C13 O1 163.7(3) . . . . ?
C7 C8 C13 O2 -17.7(3) . . . . ?
C7 C9 C10 C11 -63.3(3) . . . . ?
C7 C9 C10 C22 111.5(3) . . . . ?
C7 C9 C16 C17 -39.3(4) . . . . ?
C7 C9 C16 C21 141.4(2) . . . . ?
C8 C7 C9 C10 91.4(2) . . . . ?
C8 C7 C9 C16 -110.2(3) . . . . ?
C8 C9 C10 C11 -1.2(3) . . . . ?
C8 C9 C10 C22 173.7(2) . . . . ?
C8 C9 C16 C17 -111.4(3) . . . . ?
C8 C9 C16 C21 69.3(3) . . . . ?
C8 C13 O2 C14 -177.0(2) . . . . ?
C9 C7 C8 C12 -92.9(3) . . . . ?
C9 C7 C8 C13 108.6(2) . . . . ?
C9 C8 C12 C11 -4.8(3) . . . . ?
C9 C8 C13 O1 -127.7(3) . . . . ?
C9 C8 C13 O2 50.9(3) . . . . ?
C9 C10 C11 C12 -2.0(3) . . . . ?
C9 C10 C22 O5 -0.8(4) . . . . ?
C9 C10 C22 O6 -179.9(2) . . . . ?
C9 C16 C17 C18 179.6(2) . . . . ?
C9 C16 C21 C20 179.2(2) . . . . ?
C10 C9 C16 C17 118.1(3) . . . . ?
C10 C9 C16 C21 -61.2(3) . . . . ?
C10 C11 C12 C8 4.3(3) . . . . ?
C10 C22 O6 C23 -179.4(3) . . . . ?
C11 C10 C22 O5 173.3(3) . . . . ?
C11 C10 C22 O6 -5.8(4) . . . . ?
C12 C8 C9 C7 114.4(2) . . . . ?
C12 C8 C9 C10 3.7(3) . . . . ?
C12 C8 C9 C16 -133.0(2) . . . . ?
C12 C8 C13 O1 5.0(4) . . . . ?
C12 C8 C13 O2 -176.5(2) . . . . ?
C13 C8 C9 C7 -108.3(3) . . . . ?
C13 C8 C9 C10 141.0(2) . . . . ?
C13 C8 C9 C16 4.3(3) . . . . ?
C13 C8 C12 C11 -142.7(2) . . . . ?
C15 C14 O2 C13 87.5(4) . . . . ?
C16 C9 C10 C11 137.2(2) . . . . ?
C16 C9 C10 C22 -47.9(3) . . . . ?
C16 C17 C18 C19 1.4(4) . . . . ?
C17 C16 C21 C20 -0.1(4) . . . . ?
C17 C18 C19 C20 -0.6(4) . . . . ?
C17 C18 C19 N1 -179.5(3) . . . . ?
C18 C19 C20 C21 -0.6(4) . . . . ?
C18 C19 N1 O3 15.2(4) . . . . ?
C18 C19 N1 O4 -166.6(3) . . . . ?
C19 C20 C21 C16 0.9(4) . . . . ?
C20 C19 N1 O3 -163.8(3) . . . . ?
C20 C19 N1 O4 14.4(4) . . . . ?
C21 C16 C17 C18 -1.1(4) . . . . ?
C22 C10 C11 C12 -176.5(2) . . . . ?
N1 C19 C20 C21 178.4(2) . . . . ?
O1 C13 O2 C14 1.5(4) . . . . ?
O5 C22 O6 C23 1.5(5) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
