# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1021624'
_audit_update_record             
;
2014-08-28 deposited with the CCDC.
2015-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H13 N O2'
_chemical_formula_sum            'C16 H13 N O2'
_chemical_formula_weight         251.27

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c 21'
_symmetry_space_group_name_Hall  'P 2c -2b'

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

_cell_length_a                   9.837(2)
_cell_length_b                   16.124(4)
_cell_length_c                   8.643(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1370.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1231
_cell_measurement_theta_min      4.1450
_cell_measurement_theta_max      25.6390

_exptl_crystal_description       Prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9785
_exptl_absorpt_correction_T_max  0.9936
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3712
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4759
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0347
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         25.01
_reflns_number_total             1994
_reflns_number_gt                1322
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    Sir92
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1120P)²+1.1198P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2(8)
_refine_ls_number_reflns         1994
_refine_ls_number_parameters     136
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1254
_refine_ls_R_factor_gt           0.0880
_refine_ls_wR_factor_ref         0.2702
_refine_ls_wR_factor_gt          0.2350
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9031(2) 0.07570(11) 0.5704(7) 0.117(3) Uani 1 1 d . . .
C2 C 0.9245(2) 0.16331(11) 0.5677(7) 0.0863(17) Uani 1 1 d R . .
C3 C 1.0414(2) 0.21161(11) 0.5613(7) 0.148(3) Uani 1 1 d R . .
H3 H 1.1265 0.1864 0.5589 0.178 Uiso 1 1 calc R . .
C4 C 1.0313(2) 0.29758(11) 0.5586(7) 0.152(4) Uani 1 1 d R . .
H4 H 1.1095 0.3299 0.5543 0.182 Uiso 1 1 calc R . .
C5 C 0.9042(2) 0.33525(11) 0.5622(7) 0.153(4) Uani 1 1 d R . .
H5 H 0.8975 0.3928 0.5603 0.184 Uiso 1 1 calc R . .
C6 C 0.7873(2) 0.28695(11) 0.5685(7) 0.145(3) Uani 1 1 d R . .
H6 H 0.7023 0.3122 0.5709 0.175 Uiso 1 1 calc R . .
C7 C 0.7975(2) 0.20098(11) 0.5713(7) 0.0715(14) Uani 1 1 d R . .
C8 C 0.6951(4) 0.1359(2) 0.5689(11) 0.0684(14) Uani 1 1 d . . .
N1 N 0.7642(3) 0.06196(18) 0.5704(10) 0.0605(10) Uani 1 1 d . . .
O1 O 0.9845(4) 0.0218(3) 0.583(2) 0.246(6) Uani 1 1 d . . .
O2 O 0.5744(2) 0.14203(13) 0.5682(7) 0.139(2) Uani 1 1 d . . .
C9 C 0.7006(2) -0.01617(13) 0.5643(7) 0.0776(16) Uani 1 1 d R . .
C10 C 0.6653(2) -0.06152(13) 0.6951(7) 0.107(3) Uani 1 1 d R . .
C11 C 0.6074(2) -0.13970(13) 0.6793(7) 0.158(5) Uani 1 1 d R . .
H11 H 0.5838 -0.1700 0.7668 0.190 Uiso 1 1 calc R . .
C12 C 0.5848(2) -0.17254(13) 0.5329(7) 0.219(10) Uani 1 1 d R . .
H12 H 0.5461 -0.2249 0.5223 0.263 Uiso 1 1 calc R . .
C13 C 0.6202(2) -0.12719(13) 0.4021(7) 0.225(10) Uani 1 1 d R . .
H13 H 0.6051 -0.1492 0.3041 0.271 Uiso 1 1 calc R . .
C14 C 0.6781(2) -0.04901(13) 0.4179(7) 0.130(5) Uani 1 1 d R . .
C15 C 0.6963(12) -0.0185(7) 0.8481(16) 0.151(6) Uani 1 1 d . . .
H151 H 0.6710 -0.0541 0.9323 0.227 Uiso 1 1 calc R . .
H153 H 0.6457 0.0323 0.8543 0.227 Uiso 1 1 calc R . .
H152 H 0.7918 -0.0066 0.8540 0.227 Uiso 1 1 calc R . .
C16 C 0.7035(19) -0.0069(13) 0.2737(15) 0.208(8) Uani 1 1 d . . .
H163 H 0.6773 -0.0421 0.1892 0.313 Uiso 1 1 calc R . .
H161 H 0.7985 0.0059 0.2657 0.313 Uiso 1 1 calc R . .
H162 H 0.6515 0.0435 0.2703 0.313 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.187(4) . ?
C1 N1 1.384(4) . ?
C1 C2 1.4285 . ?
C2 C3 1.3900 . ?
C2 C7 1.3900 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 C7 1.3900 . ?
C6 H6 0.9300 . ?
C7 C8 1.454(4) . ?
C8 O2 1.192(5) . ?
C8 N1 1.373(5) . ?
N1 C9 1.408(4) . ?
C9 C10 1.3900 . ?
C9 C14 1.3900 . ?
C10 C11 1.3900 . ?
C10 C15 1.524(18) . ?
C11 C12 1.3900 . ?
C11 H11 0.9300 . ?
C12 C13 1.3900 . ?
C12 H12 0.9300 . ?
C13 C14 1.3900 . ?
C13 H13 0.9300 . ?
C14 C16 1.44(2) . ?
C15 H151 0.9600 . ?
C15 H153 0.9600 . ?
C15 H152 0.9600 . ?
C16 H163 0.9600 . ?
C16 H161 0.9600 . ?
C16 H162 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 123.3(3) . . ?
O1 C1 C2 128.7(2) . . ?
N1 C1 C2 107.70(14) . . ?
C3 C2 C7 120.0 . . ?
C3 C2 C1 132.6 . . ?
C7 C2 C1 107.4 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 120.0 . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C2 120.0 . . ?
C6 C7 C8 132.03(18) . . ?
C2 C7 C8 107.87(18) . . ?
O2 C8 N1 124.4(3) . . ?
O2 C8 C7 129.1(3) . . ?
N1 C8 C7 106.5(3) . . ?
C8 N1 C1 110.5(3) . . ?
C8 N1 C9 123.8(3) . . ?
C1 N1 C9 125.6(2) . . ?
C10 C9 C14 120.0 . . ?
C10 C9 N1 123.5(4) . . ?
C14 C9 N1 116.5(4) . . ?
C11 C10 C9 120.0 . . ?
C11 C10 C15 125.4(4) . . ?
C9 C10 C15 114.6(4) . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.0 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 120.0 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 120.0 . . ?
C13 C14 C16 114.5(7) . . ?
C9 C14 C16 125.5(7) . . ?
C10 C15 H151 109.5 . . ?
C10 C15 H153 109.5 . . ?
H151 C15 H153 109.5 . . ?
C10 C15 H152 109.5 . . ?
H151 C15 H152 109.5 . . ?
H153 C15 H152 109.5 . . ?
C14 C16 H163 109.5 . . ?
C14 C16 H161 109.5 . . ?
H163 C16 H161 109.5 . . ?
C14 C16 H162 109.5 . . ?
H163 C16 H162 109.5 . . ?
H161 C16 H162 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 8.3(12) . . . . ?
N1 C1 C2 C3 -177.5(5) . . . . ?
O1 C1 C2 C7 -172.3(12) . . . . ?
N1 C1 C2 C7 2.0(5) . . . . ?
C7 C2 C3 C4 0.0 . . . . ?
C1 C2 C3 C4 179.4 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C5 C6 C7 C2 0.0 . . . . ?
C5 C6 C7 C8 -176.0(6) . . . . ?
C3 C2 C7 C6 0.0 . . . . ?
C1 C2 C7 C6 -179.5 . . . . ?
C3 C2 C7 C8 176.9(5) . . . . ?
C1 C2 C7 C8 -2.7(5) . . . . ?
C6 C7 C8 O2 -2.3(14) . . . . ?
C2 C7 C8 O2 -178.7(9) . . . . ?
C6 C7 C8 N1 178.7(4) . . . . ?
C2 C7 C8 N1 2.4(7) . . . . ?
O2 C8 N1 C1 179.8(10) . . . . ?
C7 C8 N1 C1 -1.2(8) . . . . ?
O2 C8 N1 C9 3.0(13) . . . . ?
C7 C8 N1 C9 -178.1(8) . . . . ?
O1 C1 N1 C8 174.2(12) . . . . ?
C2 C1 N1 C8 -0.4(7) . . . . ?
O1 C1 N1 C9 -9.0(15) . . . . ?
C2 C1 N1 C9 176.4(7) . . . . ?
C8 N1 C9 C10 -92.8(8) . . . . ?
C1 N1 C9 C10 90.8(8) . . . . ?
C8 N1 C9 C14 89.6(7) . . . . ?
C1 N1 C9 C14 -86.8(8) . . . . ?
C14 C9 C10 C11 0.0 . . . . ?
N1 C9 C10 C11 -177.53(17) . . . . ?
C14 C9 C10 C15 179.6(4) . . . . ?
N1 C9 C10 C15 2.1(4) . . . . ?
C9 C10 C11 C12 0.0 . . . . ?
C15 C10 C11 C12 -179.6(5) . . . . ?
C10 C11 C12 C13 0.0 . . . . ?
C11 C12 C13 C14 0.0 . . . . ?
C12 C13 C14 C9 0.0 . . . . ?
C12 C13 C14 C16 -177.0(7) . . . . ?
C10 C9 C14 C13 0.0 . . . . ?
N1 C9 C14 C13 177.70(16) . . . . ?
C10 C9 C14 C16 176.6(8) . . . . ?
N1 C9 C14 C16 -5.7(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1021625'
_audit_update_record             
;
2014-08-28 deposited with the CCDC.
2015-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '4(C17 H13 N O4), C7 H7'
_chemical_formula_sum            'C75 H59 N4 O16'
_chemical_formula_weight         1272.26

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3591(3)
_cell_length_b                   10.4196(7)
_cell_length_c                   19.0455(9)
_cell_angle_alpha                88.407(5)
_cell_angle_beta                 88.481(3)
_cell_angle_gamma                76.340(4)
_cell_volume                     1610.95(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3866
_cell_measurement_theta_min      3.7260
_cell_measurement_theta_max      27.4620

_exptl_crystal_description       plaquet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             665
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9489
_exptl_absorpt_correction_T_max  0.9935
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3712
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11980
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         25.02
_reflns_number_total             5663
_reflns_number_gt                3983
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    Shelxs86
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0548P)²+0.3267P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5663
_refine_ls_number_parameters     438
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1247
_refine_ls_wR_factor_gt          0.1082
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C51 C 0.8163(10) 0.5745(8) 0.1245(4) 0.141(3) Uani 0.50 1 d P . .
H51A H 0.8166 0.4948 0.1511 0.211 Uiso 0.50 1 calc PR . .
H51B H 0.7051 0.6183 0.1134 0.211 Uiso 0.50 1 calc PR . .
H51C H 0.8639 0.6316 0.1517 0.211 Uiso 0.50 1 calc PR . .
C52 C 0.9095(5) 0.5431(6) 0.0615(2) 0.1236(13) Uani 1 1 d . . .
C53 C 0.9339(4) 0.4136(5) 0.0418(2) 0.1175(12) Uani 1 1 d . . .
H53 H 0.8906 0.3543 0.0693 0.141 Uiso 1 1 calc R . .
C54 C 1.0211(5) 0.3725(5) -0.0178(2) 0.1251(13) Uani 1 1 d . . .
H54 H 1.0357 0.2848 -0.0302 0.150 Uiso 1 1 calc R . .
N1 N 0.90485(17) 0.87116(17) 0.33499(9) 0.0492(4) Uani 1 1 d . . .
O1 O 0.99993(16) 1.04526(16) 0.37699(8) 0.0658(4) Uani 1 1 d . . .
O2 O 0.73331(17) 0.73560(16) 0.30723(9) 0.0679(4) Uani 1 1 d . . .
O3 O 0.44664(18) 1.35893(17) 0.49835(9) 0.0722(5) Uani 1 1 d . . .
O4 O 0.21802(16) 1.28950(17) 0.48684(9) 0.0754(5) Uani 1 1 d . . .
H4O H 0.1805 1.3539 0.5111 0.098 Uiso 1 1 calc R . .
C1 C 0.7535(2) 0.8354(2) 0.33208(11) 0.0488(5) Uani 1 1 d . . .
C2 C 0.6306(2) 0.9447(2) 0.36530(10) 0.0452(5) Uani 1 1 d . . .
C3 C 0.4629(2) 0.9614(2) 0.37610(11) 0.0529(5) Uani 1 1 d . . .
H3 H 0.4081 0.9001 0.3603 0.064 Uiso 1 1 calc R . .
C4 C 0.3792(2) 1.0727(2) 0.41135(10) 0.0514(5) Uani 1 1 d . . .
H4 H 0.2663 1.0861 0.4196 0.062 Uiso 1 1 calc R . .
C5 C 0.4609(2) 1.1647(2) 0.43453(10) 0.0448(5) Uani 1 1 d . . .
C6 C 0.6296(2) 1.1487(2) 0.42164(10) 0.0471(5) Uani 1 1 d . . .
H6 H 0.6844 1.2113 0.4358 0.056 Uiso 1 1 calc R . .
C7 C 0.7116(2) 1.0374(2) 0.38733(10) 0.0446(5) Uani 1 1 d . . .
C8 C 0.8888(2) 0.9925(2) 0.36764(10) 0.0490(5) Uani 1 1 d . . .
C9 C 0.3713(2) 1.2796(2) 0.47551(10) 0.0495(5) Uani 1 1 d . . .
C10 C 1.0577(2) 0.7908(2) 0.30808(11) 0.0495(5) Uani 1 1 d . . .
C11 C 1.1741(2) 0.7242(2) 0.35505(12) 0.0591(6) Uani 1 1 d . . .
C12 C 1.3174(3) 0.6446(3) 0.32678(18) 0.0786(8) Uani 1 1 d . . .
H12 H 1.3985 0.5987 0.3567 0.094 Uiso 1 1 calc R . .
C13 C 1.3410(3) 0.6327(3) 0.2557(2) 0.0916(9) Uani 1 1 d . . .
H13 H 1.4372 0.5783 0.2378 0.110 Uiso 1 1 calc R . .
C14 C 1.2251(3) 0.6999(3) 0.21095(16) 0.0852(8) Uani 1 1 d . . .
H14 H 1.2427 0.6901 0.1628 0.102 Uiso 1 1 calc R . .
C15 C 1.0808(3) 0.7827(2) 0.23583(12) 0.0640(6) Uani 1 1 d . . .
C16 C 1.1511(3) 0.7383(3) 0.43253(13) 0.0832(8) Uani 1 1 d . . .
H16A H 1.1863 0.8148 0.4467 0.125 Uiso 1 1 calc R . .
H16B H 1.2152 0.6611 0.4559 0.125 Uiso 1 1 calc R . .
H16C H 1.0368 0.7482 0.4449 0.125 Uiso 1 1 calc R . .
C17 C 0.9574(4) 0.8615(3) 0.18602(14) 0.0951(9) Uani 1 1 d . . .
H17A H 1.0079 0.8641 0.1403 0.143 Uiso 1 1 calc R . .
H17B H 0.9193 0.9499 0.2027 0.143 Uiso 1 1 calc R . .
H17C H 0.8658 0.8211 0.1832 0.143 Uiso 1 1 calc R . .
N21 N 0.31386(18) 0.19392(19) 0.16752(9) 0.0563(5) Uani 1 1 d . . .
O21 O 0.44208(16) 0.28519(17) 0.25283(8) 0.0688(5) Uani 1 1 d . . .
O22 O 0.11684(18) 0.11994(19) 0.10736(9) 0.0797(5) Uani 1 1 d . . .
O23 O -0.07473(17) 0.52140(16) 0.42604(8) 0.0644(4) Uani 1 1 d . . .
O24 O -0.31232(16) 0.47159(16) 0.40319(8) 0.0633(4) Uani 1 1 d . . .
H24O H -0.3431 0.5175 0.4375 0.082 Uiso 1 1 calc R . .
C21 C 0.1554(2) 0.1765(2) 0.15613(11) 0.0592(6) Uani 1 1 d . . .
C22 C 0.0506(2) 0.2434(2) 0.21485(10) 0.0534(5) Uani 1 1 d . . .
C23 C -0.1162(2) 0.2599(2) 0.22817(11) 0.0576(6) Uani 1 1 d . . .
H23 H -0.1811 0.2234 0.1993 0.069 Uiso 1 1 calc R . .
C24 C -0.1830(2) 0.3325(2) 0.28583(11) 0.0534(5) Uani 1 1 d . . .
H24 H -0.2950 0.3454 0.2960 0.064 Uiso 1 1 calc R . .
C25 C -0.0853(2) 0.3870(2) 0.32906(10) 0.0459(5) Uani 1 1 d . . .
C26 C 0.0828(2) 0.3686(2) 0.31536(10) 0.0485(5) Uani 1 1 d . . .
H26 H 0.1486 0.4046 0.3440 0.058 Uiso 1 1 calc R . .
C27 C 0.1482(2) 0.2958(2) 0.25820(10) 0.0485(5) Uani 1 1 d . . .
C28 C 0.3200(2) 0.2619(2) 0.22946(11) 0.0533(5) Uani 1 1 d . . .
C29 C -0.1599(2) 0.4663(2) 0.39012(10) 0.0467(5) Uani 1 1 d . . .
C30 C 0.4502(2) 0.1549(2) 0.11885(11) 0.0553(6) Uani 1 1 d . . .
C31 C 0.4975(3) 0.2531(3) 0.07821(12) 0.0681(7) Uani 1 1 d . . .
C32 C 0.6267(3) 0.2135(3) 0.03042(13) 0.0841(8) Uani 1 1 d . . .
H32 H 0.6618 0.2768 0.0026 0.101 Uiso 1 1 calc R . .
C33 C 0.7033(3) 0.0830(4) 0.02343(15) 0.0901(10) Uani 1 1 d . . .
H33 H 0.7899 0.0584 -0.0088 0.108 Uiso 1 1 calc R . .
C34 C 0.6529(3) -0.0118(3) 0.06377(15) 0.0829(9) Uani 1 1 d . . .
H34 H 0.7047 -0.1003 0.0579 0.099 Uiso 1 1 calc R . .
C35 C 0.5255(2) 0.0223(3) 0.11329(12) 0.0661(7) Uani 1 1 d . . .
C36 C 0.4131(4) 0.3967(3) 0.08465(17) 0.0966(9) Uani 1 1 d . . .
H36A H 0.4457 0.4297 0.1272 0.145 Uiso 1 1 calc R . .
H36B H 0.2960 0.4066 0.0857 0.145 Uiso 1 1 calc R . .
H36C H 0.4437 0.4457 0.0451 0.145 Uiso 1 1 calc R . .
C37 C 0.4713(3) -0.0808(3) 0.15737(17) 0.0946(9) Uani 1 1 d . . .
H37A H 0.4744 -0.0604 0.2061 0.142 Uiso 1 1 calc R . .
H37B H 0.5436 -0.1654 0.1488 0.142 Uiso 1 1 calc R . .
H37C H 0.3610 -0.0828 0.1456 0.142 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C51 C52 1.415(8) . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C52 C53 1.378(6) . ?
C52 C54 1.407(6) 2_765 ?
C53 C54 1.355(5) . ?
C53 H53 0.9300 . ?
C54 C52 1.407(6) 2_765 ?
C54 H54 0.9300 . ?
N1 C8 1.400(3) . ?
N1 C1 1.404(2) . ?
N1 C10 1.442(2) . ?
O1 C8 1.206(2) . ?
O2 C1 1.203(2) . ?
O3 C9 1.245(2) . ?
O4 C9 1.274(2) . ?
O4 H4O 0.8200 . ?
C1 C2 1.485(3) . ?
C2 C3 1.381(2) . ?
C2 C7 1.384(3) . ?
C3 C4 1.386(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(2) . ?
C5 C9 1.484(3) . ?
C6 C7 1.374(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.485(3) . ?
C10 C11 1.386(3) . ?
C10 C15 1.387(3) . ?
C11 C12 1.391(3) . ?
C11 C16 1.490(3) . ?
C12 C13 1.368(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.358(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.387(3) . ?
C14 H14 0.9300 . ?
C15 C17 1.499(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N21 C28 1.401(2) . ?
N21 C21 1.402(3) . ?
N21 C30 1.439(2) . ?
O21 C28 1.202(2) . ?
O22 C21 1.204(2) . ?
O23 C29 1.243(2) . ?
O24 C29 1.280(2) . ?
O24 H24O 0.8200 . ?
C21 C22 1.485(3) . ?
C22 C23 1.381(3) . ?
C22 C27 1.385(3) . ?
C23 C24 1.380(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.395(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.392(2) . ?
C25 C29 1.482(3) . ?
C26 C27 1.371(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.489(3) . ?
C30 C35 1.381(3) . ?
C30 C31 1.391(3) . ?
C31 C32 1.387(3) . ?
C31 C36 1.503(4) . ?
C32 C33 1.369(4) . ?
C32 H32 0.9300 . ?
C33 C34 1.371(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.392(3) . ?
C34 H34 0.9300 . ?
C35 C37 1.491(4) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C52 C51 H51A 109.5 . . ?
C52 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C52 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
C53 C52 C54 117.2(4) . 2_765 ?
C53 C52 C51 114.9(6) . . ?
C54 C52 C51 127.9(6) 2_765 . ?
C54 C53 C52 120.0(4) . . ?
C54 C53 H53 120.0 . . ?
C52 C53 H53 120.0 . . ?
C53 C54 C52 122.8(4) . 2_765 ?
C53 C54 H54 118.6 . . ?
C52 C54 H54 118.6 2_765 . ?
C8 N1 C1 111.82(15) . . ?
C8 N1 C10 124.74(15) . . ?
C1 N1 C10 123.44(16) . . ?
C9 O4 H4O 109.5 . . ?
O2 C1 N1 125.27(18) . . ?
O2 C1 C2 129.08(17) . . ?
N1 C1 C2 105.65(16) . . ?
C3 C2 C7 121.23(18) . . ?
C3 C2 C1 130.41(18) . . ?
C7 C2 C1 108.35(15) . . ?
C2 C3 C4 117.70(18) . . ?
C2 C3 H3 121.2 . . ?
C4 C3 H3 121.2 . . ?
C3 C4 C5 121.10(17) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 120.77(18) . . ?
C4 C5 C9 120.47(16) . . ?
C6 C5 C9 118.73(17) . . ?
C7 C6 C5 117.61(17) . . ?
C7 C6 H6 121.2 . . ?
C5 C6 H6 121.2 . . ?
C6 C7 C2 121.55(16) . . ?
C6 C7 C8 129.96(17) . . ?
C2 C7 C8 108.49(17) . . ?
O1 C8 N1 125.12(17) . . ?
O1 C8 C7 129.19(19) . . ?
N1 C8 C7 105.69(15) . . ?
O3 C9 O4 123.19(19) . . ?
O3 C9 C5 120.09(16) . . ?
O4 C9 C5 116.70(18) . . ?
C11 C10 C15 122.82(19) . . ?
C11 C10 N1 119.03(19) . . ?
C15 C10 N1 118.14(18) . . ?
C10 C11 C12 117.1(2) . . ?
C10 C11 C16 122.3(2) . . ?
C12 C11 C16 120.6(2) . . ?
C13 C12 C11 121.0(2) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 121.2(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C10 C15 C14 117.3(2) . . ?
C10 C15 C17 121.9(2) . . ?
C14 C15 C17 120.8(2) . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C28 N21 C21 111.75(15) . . ?
C28 N21 C30 124.26(16) . . ?
C21 N21 C30 123.85(16) . . ?
C29 O24 H24O 109.5 . . ?
O22 C21 N21 125.31(18) . . ?
O22 C21 C22 128.86(18) . . ?
N21 C21 C22 105.81(16) . . ?
C23 C22 C27 121.45(18) . . ?
C23 C22 C21 130.16(18) . . ?
C27 C22 C21 108.37(16) . . ?
C24 C23 C22 117.57(18) . . ?
C24 C23 H23 121.2 . . ?
C22 C23 H23 121.2 . . ?
C23 C24 C25 121.09(17) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C26 C25 C24 120.76(17) . . ?
C26 C25 C29 118.98(17) . . ?
C24 C25 C29 120.26(16) . . ?
C27 C26 C25 117.71(17) . . ?
C27 C26 H26 121.1 . . ?
C25 C26 H26 121.1 . . ?
C26 C27 C22 121.42(17) . . ?
C26 C27 C28 130.24(17) . . ?
C22 C27 C28 108.31(17) . . ?
O21 C28 N21 125.25(17) . . ?
O21 C28 C27 129.05(18) . . ?
N21 C28 C27 105.69(16) . . ?
O23 C29 O24 123.64(18) . . ?
O23 C29 C25 120.18(16) . . ?
O24 C29 C25 116.17(18) . . ?
C35 C30 C31 123.0(2) . . ?
C35 C30 N21 119.0(2) . . ?
C31 C30 N21 118.0(2) . . ?
C32 C31 C30 117.2(3) . . ?
C32 C31 C36 120.5(3) . . ?
C30 C31 C36 122.2(2) . . ?
C33 C32 C31 121.1(3) . . ?
C33 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?
C32 C33 C34 120.3(2) . . ?
C32 C33 H33 119.9 . . ?
C34 C33 H33 119.9 . . ?
C33 C34 C35 121.1(3) . . ?
C33 C34 H34 119.5 . . ?
C35 C34 H34 119.5 . . ?
C30 C35 C34 117.2(3) . . ?
C30 C35 C37 121.7(2) . . ?
C34 C35 C37 121.0(3) . . ?
C31 C36 H36A 109.5 . . ?
C31 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C31 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C54 C52 C53 C54 -0.3(6) 2_765 . . . ?
C51 C52 C53 C54 179.8(5) . . . . ?
C52 C53 C54 C52 0.3(6) . . . 2_765 ?
C8 N1 C1 O2 -179.5(2) . . . . ?
C10 N1 C1 O2 -0.1(3) . . . . ?
C8 N1 C1 C2 0.6(2) . . . . ?
C10 N1 C1 C2 179.90(18) . . . . ?
O2 C1 C2 C3 -0.4(4) . . . . ?
N1 C1 C2 C3 179.6(2) . . . . ?
O2 C1 C2 C7 178.9(2) . . . . ?
N1 C1 C2 C7 -1.1(2) . . . . ?
C7 C2 C3 C4 -1.6(3) . . . . ?
C1 C2 C3 C4 177.7(2) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 1.3(3) . . . . ?
C3 C4 C5 C9 -176.72(19) . . . . ?
C4 C5 C6 C7 -2.0(3) . . . . ?
C9 C5 C6 C7 176.12(18) . . . . ?
C5 C6 C7 C2 0.9(3) . . . . ?
C5 C6 C7 C8 -178.78(19) . . . . ?
C3 C2 C7 C6 0.9(3) . . . . ?
C1 C2 C7 C6 -178.46(19) . . . . ?
C3 C2 C7 C8 -179.37(19) . . . . ?
C1 C2 C7 C8 1.3(2) . . . . ?
C1 N1 C8 O1 179.8(2) . . . . ?
C10 N1 C8 O1 0.5(3) . . . . ?
C1 N1 C8 C7 0.2(2) . . . . ?
C10 N1 C8 C7 -179.16(18) . . . . ?
C6 C7 C8 O1 -0.8(4) . . . . ?
C2 C7 C8 O1 179.5(2) . . . . ?
C6 C7 C8 N1 178.8(2) . . . . ?
C2 C7 C8 N1 -0.9(2) . . . . ?
C4 C5 C9 O3 177.3(2) . . . . ?
C6 C5 C9 O3 -0.8(3) . . . . ?
C4 C5 C9 O4 -1.0(3) . . . . ?
C6 C5 C9 O4 -179.13(19) . . . . ?
C8 N1 C10 C11 72.0(3) . . . . ?
C1 N1 C10 C11 -107.2(2) . . . . ?
C8 N1 C10 C15 -108.5(2) . . . . ?
C1 N1 C10 C15 72.2(3) . . . . ?
C15 C10 C11 C12 -1.4(3) . . . . ?
N1 C10 C11 C12 178.04(19) . . . . ?
C15 C10 C11 C16 177.2(2) . . . . ?
N1 C10 C11 C16 -3.4(3) . . . . ?
C10 C11 C12 C13 -0.3(4) . . . . ?
C16 C11 C12 C13 -178.9(3) . . . . ?
C11 C12 C13 C14 0.7(4) . . . . ?
C12 C13 C14 C15 0.5(5) . . . . ?
C11 C10 C15 C14 2.5(3) . . . . ?
N1 C10 C15 C14 -176.9(2) . . . . ?
C11 C10 C15 C17 -176.5(2) . . . . ?
N1 C10 C15 C17 4.0(3) . . . . ?
C13 C14 C15 C10 -2.1(4) . . . . ?
C13 C14 C15 C17 177.0(3) . . . . ?
C28 N21 C21 O22 -179.0(2) . . . . ?
C30 N21 C21 O22 5.1(4) . . . . ?
C28 N21 C21 C22 2.0(3) . . . . ?
C30 N21 C21 C22 -173.9(2) . . . . ?
O22 C21 C22 C23 -1.2(4) . . . . ?
N21 C21 C22 C23 177.8(2) . . . . ?
O22 C21 C22 C27 -179.4(3) . . . . ?
N21 C21 C22 C27 -0.5(3) . . . . ?
C27 C22 C23 C24 1.0(3) . . . . ?
C21 C22 C23 C24 -177.0(2) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C23 C24 C25 C26 -0.4(3) . . . . ?
C23 C24 C25 C29 179.1(2) . . . . ?
C24 C25 C26 C27 0.1(3) . . . . ?
C29 C25 C26 C27 -179.46(19) . . . . ?
C25 C26 C27 C22 0.8(3) . . . . ?
C25 C26 C27 C28 178.5(2) . . . . ?
C23 C22 C27 C26 -1.4(3) . . . . ?
C21 C22 C27 C26 177.0(2) . . . . ?
C23 C22 C27 C28 -179.5(2) . . . . ?
C21 C22 C27 C28 -1.1(3) . . . . ?
C21 N21 C28 O21 176.9(2) . . . . ?
C30 N21 C28 O21 -7.2(4) . . . . ?
C21 N21 C28 C27 -2.7(3) . . . . ?
C30 N21 C28 C27 173.2(2) . . . . ?
C26 C27 C28 O21 4.8(4) . . . . ?
C22 C27 C28 O21 -177.3(2) . . . . ?
C26 C27 C28 N21 -175.6(2) . . . . ?
C22 C27 C28 N21 2.3(3) . . . . ?
C26 C25 C29 O23 3.9(3) . . . . ?
C24 C25 C29 O23 -175.6(2) . . . . ?
C26 C25 C29 O24 -174.99(18) . . . . ?
C24 C25 C29 O24 5.5(3) . . . . ?
C28 N21 C30 C35 110.2(2) . . . . ?
C21 N21 C30 C35 -74.5(3) . . . . ?
C28 N21 C30 C31 -71.3(3) . . . . ?
C21 N21 C30 C31 104.0(3) . . . . ?
C35 C30 C31 C32 -0.1(3) . . . . ?
N21 C30 C31 C32 -178.54(19) . . . . ?
C35 C30 C31 C36 179.5(2) . . . . ?
N21 C30 C31 C36 1.1(3) . . . . ?
C30 C31 C32 C33 0.4(4) . . . . ?
C36 C31 C32 C33 -179.2(3) . . . . ?
C31 C32 C33 C34 0.2(4) . . . . ?
C32 C33 C34 C35 -1.1(4) . . . . ?
C31 C30 C35 C34 -0.8(3) . . . . ?
N21 C30 C35 C34 177.66(19) . . . . ?
C31 C30 C35 C37 -179.7(2) . . . . ?
N21 C30 C35 C37 -1.2(3) . . . . ?
C33 C34 C35 C30 1.4(4) . . . . ?
C33 C34 C35 C37 -179.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.030

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1021626'
_audit_update_record             
;
2014-08-28 deposited with the CCDC.
2015-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H13 N O4'
_chemical_formula_sum            'C17 H13 N O4'
_chemical_formula_weight         295.28

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4040(5)
_cell_length_b                   11.6930(10)
_cell_length_c                   15.2400(10)
_cell_angle_alpha                97.881(6)
_cell_angle_beta                 93.354(5)
_cell_angle_gamma                96.810(6)
_cell_volume                     1468.73(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1841
_cell_measurement_theta_min      3.4470
_cell_measurement_theta_max      21.2320

_exptl_crystal_description       plaquet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9580
_exptl_absorpt_correction_T_max  0.9895
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3712
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10179
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_sigmaI/netI    0.1105
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         23.26
_reflns_number_total             4188
_reflns_number_gt                2204
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    Shelxs86
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0521P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4188
_refine_ls_number_parameters     400
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1557
_refine_ls_R_factor_gt           0.0705
_refine_ls_wR_factor_ref         0.1574
_refine_ls_wR_factor_gt          0.1271
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.026
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6330(4) 0.2055(3) 0.1521(2) 0.0552(11) Uani 1 1 d . . .
O1 O 0.4162(3) 0.2640(3) 0.0768(2) 0.0810(12) Uani 1 1 d . . .
O2 O 0.7882(3) 0.1287(3) 0.2539(2) 0.0704(11) Uani 1 1 d . . .
O3 O 0.0888(4) -0.0432(3) 0.4205(2) 0.0668(10) Uani 1 1 d . . .
H3O H 0.0715 -0.0883 0.4566 0.087 Uiso 1 1 calc R . .
O4 O 0.3398(4) -0.0785(3) 0.4491(2) 0.0725(11) Uani 1 1 d . . .
C1 C 0.4708(5) 0.2169(4) 0.1359(3) 0.0566(14) Uani 1 1 d . . .
C2 C 0.3855(5) 0.1590(4) 0.2036(3) 0.0508(13) Uani 1 1 d . . .
C3 C 0.2236(5) 0.1420(4) 0.2169(3) 0.0568(14) Uani 1 1 d . . .
H3 H 0.1484 0.1710 0.1816 0.068 Uiso 1 1 calc R . .
C4 C 0.1766(5) 0.0800(4) 0.2849(3) 0.0535(13) Uani 1 1 d . . .
H4 H 0.0685 0.0684 0.2959 0.064 Uiso 1 1 calc R . .
C5 C 0.2893(5) 0.0350(4) 0.3368(3) 0.0493(13) Uani 1 1 d . . .
C6 C 0.4522(5) 0.0535(4) 0.3226(3) 0.0489(12) Uani 1 1 d . . .
H6 H 0.5282 0.0237 0.3568 0.059 Uiso 1 1 calc R . .
C7 C 0.4969(5) 0.1170(4) 0.2568(3) 0.0464(12) Uani 1 1 d . . .
C8 C 0.6583(5) 0.1474(4) 0.2251(3) 0.0560(13) Uani 1 1 d . . .
C9 C 0.2375(5) -0.0332(4) 0.4064(3) 0.0528(13) Uani 1 1 d . . .
C10 C 0.7617(5) 0.2468(6) 0.1025(3) 0.0583(14) Uani 1 1 d . . .
C11 C 0.8187(6) 0.3659(6) 0.1154(3) 0.0687(16) Uani 1 1 d . . .
C12 C 0.9539(7) 0.3996(7) 0.0728(4) 0.103(3) Uani 1 1 d . . .
H12 H 0.9956 0.4779 0.0800 0.124 Uiso 1 1 calc R . .
C13 C 1.0258(8) 0.3218(10) 0.0216(6) 0.121(4) Uani 1 1 d . . .
H13 H 1.1192 0.3472 -0.0037 0.146 Uiso 1 1 calc R . .
C14 C 0.9663(8) 0.2066(9) 0.0055(5) 0.129(3) Uani 1 1 d . . .
H14 H 1.0164 0.1549 -0.0322 0.155 Uiso 1 1 calc R . .
C15 C 0.8277(7) 0.1661(7) 0.0464(4) 0.089(2) Uani 1 1 d . . .
C16 C 0.7306(8) 0.4530(6) 0.1658(4) 0.104(2) Uani 1 1 d . . .
H16A H 0.6401 0.4136 0.1899 0.156 Uiso 1 1 calc R . .
H16B H 0.6938 0.5038 0.1268 0.156 Uiso 1 1 calc R . .
H16C H 0.8010 0.4978 0.2134 0.156 Uiso 1 1 calc R . .
C17 C 0.7585(9) 0.0393(7) 0.0289(5) 0.137(3) Uani 1 1 d . . .
H17A H 0.7790 0.0037 0.0808 0.205 Uiso 1 1 calc R . .
H17B H 0.8078 0.0006 -0.0201 0.205 Uiso 1 1 calc R . .
H17C H 0.6446 0.0329 0.0147 0.205 Uiso 1 1 calc R . .
N21 N 0.3509(4) 0.6148(3) 0.3006(2) 0.0506(10) Uani 1 1 d . . .
O21 O 0.1596(4) 0.7397(3) 0.2861(2) 0.0701(10) Uani 1 1 d . . .
O22 O 0.4736(4) 0.4574(3) 0.3325(2) 0.0723(11) Uani 1 1 d . . .
O23 O -0.2410(3) 0.2497(3) 0.46311(19) 0.0704(10) Uani 1 1 d . . .
H23O H -0.2630 0.1944 0.4899 0.091 Uiso 1 1 calc R . .
O24 O 0.0032(4) 0.1929(3) 0.4729(2) 0.0658(10) Uani 1 1 d . . .
C21 C 0.1971(5) 0.6504(5) 0.3065(3) 0.0516(13) Uani 1 1 d . . .
C22 C 0.0975(5) 0.5554(4) 0.3415(3) 0.0452(12) Uani 1 1 d . . .
C23 C -0.0604(5) 0.5465(4) 0.3610(3) 0.0528(13) Uani 1 1 d . . .
H23 H -0.1231 0.6051 0.3525 0.063 Uiso 1 1 calc R . .
C24 C -0.1231(5) 0.4476(4) 0.3938(3) 0.0519(13) Uani 1 1 d . . .
H24 H -0.2307 0.4381 0.4058 0.062 Uiso 1 1 calc R . .
C25 C -0.0269(5) 0.3620(4) 0.4092(2) 0.0470(12) Uani 1 1 d . . .
C26 C 0.1328(5) 0.3733(4) 0.3892(2) 0.0464(12) Uani 1 1 d . . .
H26 H 0.1973 0.3161 0.3985 0.056 Uiso 1 1 calc R . .
C27 C 0.1935(5) 0.4712(4) 0.3553(2) 0.0450(12) Uani 1 1 d . . .
C28 C 0.3570(5) 0.5071(5) 0.3297(3) 0.0534(13) Uani 1 1 d . . .
C29 C -0.0907(6) 0.2605(5) 0.4505(3) 0.0542(14) Uani 1 1 d . . .
C30 C 0.4859(5) 0.6844(4) 0.2718(3) 0.0478(12) Uani 1 1 d . . .
C31 C 0.4899(5) 0.6917(5) 0.1827(3) 0.0613(14) Uani 1 1 d . . .
C32 C 0.6195(6) 0.7602(5) 0.1554(4) 0.0785(18) Uani 1 1 d . . .
H32 H 0.6249 0.7679 0.0957 0.094 Uiso 1 1 calc R . .
C33 C 0.7382(7) 0.8159(5) 0.2163(4) 0.0819(18) Uani 1 1 d . . .
H33 H 0.8250 0.8611 0.1977 0.098 Uiso 1 1 calc R . .
C34 C 0.7316(5) 0.8063(5) 0.3037(4) 0.0675(15) Uani 1 1 d . . .
H34 H 0.8147 0.8449 0.3437 0.081 Uiso 1 1 calc R . .
C35 C 0.6052(5) 0.7410(4) 0.3350(3) 0.0522(13) Uani 1 1 d . . .
C36 C 0.3599(6) 0.6273(6) 0.1152(3) 0.098(2) Uani 1 1 d . . .
H36A H 0.3368 0.5484 0.1263 0.147 Uiso 1 1 calc R . .
H36B H 0.3958 0.6276 0.0566 0.147 Uiso 1 1 calc R . .
H36C H 0.2645 0.6648 0.1198 0.147 Uiso 1 1 calc R . .
C37 C 0.6004(6) 0.7300(5) 0.4312(3) 0.0747(16) Uani 1 1 d . . .
H37A H 0.4941 0.7376 0.4492 0.112 Uiso 1 1 calc R . .
H37B H 0.6757 0.7901 0.4655 0.112 Uiso 1 1 calc R . .
H37C H 0.6284 0.6552 0.4409 0.112 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.396(5) . ?
N1 C8 1.400(5) . ?
N1 C10 1.429(5) . ?
O1 C1 1.214(5) . ?
O2 C8 1.207(5) . ?
O3 C9 1.275(5) . ?
O3 H3O 0.8200 . ?
O4 C9 1.258(5) . ?
C1 C2 1.483(5) . ?
C2 C7 1.380(5) . ?
C2 C3 1.383(5) . ?
C3 C4 1.393(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(5) . ?
C5 C9 1.468(5) . ?
C6 C7 1.372(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.486(5) . ?
C10 C15 1.374(8) . ?
C10 C11 1.402(7) . ?
C11 C12 1.384(7) . ?
C11 C16 1.485(8) . ?
C12 C13 1.338(10) . ?
C12 H12 0.9300 . ?
C13 C14 1.365(11) . ?
C13 H13 0.9300 . ?
C14 C15 1.415(8) . ?
C14 H14 0.9300 . ?
C15 C17 1.509(9) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N21 C28 1.397(6) . ?
N21 C21 1.408(5) . ?
N21 C30 1.443(5) . ?
O21 C21 1.201(5) . ?
O22 C28 1.199(5) . ?
O23 C29 1.284(5) . ?
O23 H23O 0.8200 . ?
O24 C29 1.247(5) . ?
C21 C22 1.487(6) . ?
C22 C23 1.372(5) . ?
C22 C27 1.375(6) . ?
C23 C24 1.382(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.395(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.389(5) . ?
C25 C29 1.478(6) . ?
C26 C27 1.375(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.479(5) . ?
C30 C31 1.374(5) . ?
C30 C35 1.388(6) . ?
C31 C32 1.392(6) . ?
C31 C36 1.510(6) . ?
C32 C33 1.361(6) . ?
C32 H32 0.9300 . ?
C33 C34 1.355(6) . ?
C33 H33 0.9300 . ?
C34 C35 1.381(6) . ?
C34 H34 0.9300 . ?
C35 C37 1.492(5) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 111.6(3) . . ?
C1 N1 C10 126.2(3) . . ?
C8 N1 C10 122.3(3) . . ?
C9 O3 H3O 109.5 . . ?
O1 C1 N1 125.0(4) . . ?
O1 C1 C2 129.1(4) . . ?
N1 C1 C2 105.9(3) . . ?
C7 C2 C3 120.9(4) . . ?
C7 C2 C1 108.6(4) . . ?
C3 C2 C1 130.5(4) . . ?
C2 C3 C4 117.9(4) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
C3 C4 C5 120.9(4) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 120.4(4) . . ?
C6 C5 C9 119.3(4) . . ?
C4 C5 C9 120.3(4) . . ?
C7 C6 C5 118.0(4) . . ?
C7 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
C6 C7 C2 121.9(4) . . ?
C6 C7 C8 130.0(4) . . ?
C2 C7 C8 108.0(3) . . ?
O2 C8 N1 124.6(4) . . ?
O2 C8 C7 129.5(4) . . ?
N1 C8 C7 105.9(4) . . ?
O4 C9 O3 123.1(4) . . ?
O4 C9 C5 119.3(4) . . ?
O3 C9 C5 117.6(4) . . ?
C15 C10 C11 122.9(5) . . ?
C15 C10 N1 117.9(5) . . ?
C11 C10 N1 119.2(5) . . ?
C12 C11 C10 116.8(6) . . ?
C12 C11 C16 121.4(7) . . ?
C10 C11 C16 121.6(5) . . ?
C13 C12 C11 121.4(8) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C14 122.0(7) . . ?
C12 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
C13 C14 C15 119.6(8) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C10 C15 C14 117.1(7) . . ?
C10 C15 C17 122.3(5) . . ?
C14 C15 C17 120.6(7) . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C28 N21 C21 111.6(3) . . ?
C28 N21 C30 124.8(4) . . ?
C21 N21 C30 123.5(4) . . ?
C29 O23 H23O 109.5 . . ?
O21 C21 N21 125.1(4) . . ?
O21 C21 C22 129.2(4) . . ?
N21 C21 C22 105.7(4) . . ?
C23 C22 C27 122.2(4) . . ?
C23 C22 C21 129.9(4) . . ?
C27 C22 C21 107.9(4) . . ?
C22 C23 C24 117.7(4) . . ?
C22 C23 H23 121.1 . . ?
C24 C23 H23 121.1 . . ?
C23 C24 C25 120.8(4) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C26 C25 C24 120.3(4) . . ?
C26 C25 C29 118.9(4) . . ?
C24 C25 C29 120.8(4) . . ?
C27 C26 C25 118.5(4) . . ?
C27 C26 H26 120.8 . . ?
C25 C26 H26 120.8 . . ?
C22 C27 C26 120.5(4) . . ?
C22 C27 C28 109.2(4) . . ?
C26 C27 C28 130.3(4) . . ?
O22 C28 N21 125.3(4) . . ?
O22 C28 C27 129.1(4) . . ?
N21 C28 C27 105.6(4) . . ?
O24 C29 O23 124.0(4) . . ?
O24 C29 C25 119.1(4) . . ?
O23 C29 C25 116.9(5) . . ?
C31 C30 C35 123.1(4) . . ?
C31 C30 N21 118.2(4) . . ?
C35 C30 N21 118.7(4) . . ?
C30 C31 C32 117.9(4) . . ?
C30 C31 C36 121.9(4) . . ?
C32 C31 C36 120.2(4) . . ?
C33 C32 C31 119.9(4) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C34 C33 C32 120.8(5) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C33 C34 C35 122.0(5) . . ?
C33 C34 H34 119.0 . . ?
C35 C34 H34 119.0 . . ?
C34 C35 C30 116.2(4) . . ?
C34 C35 C37 121.5(4) . . ?
C30 C35 C37 122.3(4) . . ?
C31 C36 H36A 109.5 . . ?
C31 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C31 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 O1 179.8(5) . . . . ?
C10 N1 C1 O1 0.1(8) . . . . ?
C8 N1 C1 C2 -1.2(5) . . . . ?
C10 N1 C1 C2 179.1(5) . . . . ?
O1 C1 C2 C7 179.4(5) . . . . ?
N1 C1 C2 C7 0.5(5) . . . . ?
O1 C1 C2 C3 0.8(9) . . . . ?
N1 C1 C2 C3 -178.1(5) . . . . ?
C7 C2 C3 C4 -0.8(7) . . . . ?
C1 C2 C3 C4 177.7(5) . . . . ?
C2 C3 C4 C5 -1.0(7) . . . . ?
C3 C4 C5 C6 1.4(7) . . . . ?
C3 C4 C5 C9 -178.1(4) . . . . ?
C4 C5 C6 C7 0.1(7) . . . . ?
C9 C5 C6 C7 179.7(4) . . . . ?
C5 C6 C7 C2 -2.0(7) . . . . ?
C5 C6 C7 C8 -178.0(5) . . . . ?
C3 C2 C7 C6 2.3(7) . . . . ?
C1 C2 C7 C6 -176.4(4) . . . . ?
C3 C2 C7 C8 179.1(4) . . . . ?
C1 C2 C7 C8 0.3(5) . . . . ?
C1 N1 C8 O2 -178.3(5) . . . . ?
C10 N1 C8 O2 1.4(8) . . . . ?
C1 N1 C8 C7 1.3(5) . . . . ?
C10 N1 C8 C7 -178.9(4) . . . . ?
C6 C7 C8 O2 -4.9(9) . . . . ?
C2 C7 C8 O2 178.7(5) . . . . ?
C6 C7 C8 N1 175.4(4) . . . . ?
C2 C7 C8 N1 -1.0(5) . . . . ?
C6 C5 C9 O4 -3.5(7) . . . . ?
C4 C5 C9 O4 176.0(5) . . . . ?
C6 C5 C9 O3 176.5(4) . . . . ?
C4 C5 C9 O3 -4.0(7) . . . . ?
C1 N1 C10 C15 -106.2(6) . . . . ?
C8 N1 C10 C15 74.1(6) . . . . ?
C1 N1 C10 C11 76.1(6) . . . . ?
C8 N1 C10 C11 -103.6(5) . . . . ?
C15 C10 C11 C12 -4.1(7) . . . . ?
N1 C10 C11 C12 173.5(4) . . . . ?
C15 C10 C11 C16 170.9(5) . . . . ?
N1 C10 C11 C16 -11.6(7) . . . . ?
C10 C11 C12 C13 0.3(8) . . . . ?
C16 C11 C12 C13 -174.6(6) . . . . ?
C11 C12 C13 C14 2.9(11) . . . . ?
C12 C13 C14 C15 -2.4(11) . . . . ?
C11 C10 C15 C14 4.5(8) . . . . ?
N1 C10 C15 C14 -173.1(4) . . . . ?
C11 C10 C15 C17 -176.1(5) . . . . ?
N1 C10 C15 C17 6.3(8) . . . . ?
C13 C14 C15 C10 -1.2(9) . . . . ?
C13 C14 C15 C17 179.3(7) . . . . ?
C28 N21 C21 O21 179.7(4) . . . . ?
C30 N21 C21 O21 2.4(7) . . . . ?
C28 N21 C21 C22 -0.8(5) . . . . ?
C30 N21 C21 C22 -178.1(4) . . . . ?
O21 C21 C22 C23 -1.6(8) . . . . ?
N21 C21 C22 C23 178.9(4) . . . . ?
O21 C21 C22 C27 -179.8(5) . . . . ?
N21 C21 C22 C27 0.7(5) . . . . ?
C27 C22 C23 C24 -1.4(6) . . . . ?
C21 C22 C23 C24 -179.4(4) . . . . ?
C22 C23 C24 C25 2.1(6) . . . . ?
C23 C24 C25 C26 -1.9(6) . . . . ?
C23 C24 C25 C29 175.4(4) . . . . ?
C24 C25 C26 C27 0.9(6) . . . . ?
C29 C25 C26 C27 -176.5(4) . . . . ?
C23 C22 C27 C26 0.5(7) . . . . ?
C21 C22 C27 C26 178.9(4) . . . . ?
C23 C22 C27 C28 -178.8(4) . . . . ?
C21 C22 C27 C28 -0.4(5) . . . . ?
C25 C26 C27 C22 -0.2(6) . . . . ?
C25 C26 C27 C28 178.9(4) . . . . ?
C21 N21 C28 O22 -179.2(4) . . . . ?
C30 N21 C28 O22 -1.9(7) . . . . ?
C21 N21 C28 C27 0.5(5) . . . . ?
C30 N21 C28 C27 177.9(4) . . . . ?
C22 C27 C28 O22 179.7(5) . . . . ?
C26 C27 C28 O22 0.5(8) . . . . ?
C22 C27 C28 N21 -0.1(5) . . . . ?
C26 C27 C28 N21 -179.2(4) . . . . ?
C26 C25 C29 O24 5.8(6) . . . . ?
C24 C25 C29 O24 -171.6(4) . . . . ?
C26 C25 C29 O23 -176.1(4) . . . . ?
C24 C25 C29 O23 6.6(6) . . . . ?
C28 N21 C30 C31 107.7(5) . . . . ?
C21 N21 C30 C31 -75.3(6) . . . . ?
C28 N21 C30 C35 -72.5(6) . . . . ?
C21 N21 C30 C35 104.5(5) . . . . ?
C35 C30 C31 C32 -0.6(8) . . . . ?
N21 C30 C31 C32 179.2(5) . . . . ?
C35 C30 C31 C36 178.8(5) . . . . ?
N21 C30 C31 C36 -1.4(7) . . . . ?
C30 C31 C32 C33 1.0(8) . . . . ?
C36 C31 C32 C33 -178.5(6) . . . . ?
C31 C32 C33 C34 -0.5(9) . . . . ?
C32 C33 C34 C35 -0.4(9) . . . . ?
C33 C34 C35 C30 0.8(8) . . . . ?
C33 C34 C35 C37 179.2(5) . . . . ?
C31 C30 C35 C34 -0.2(7) . . . . ?
N21 C30 C35 C34 180.0(4) . . . . ?
C31 C30 C35 C37 -178.7(5) . . . . ?
N21 C30 C35 C37 1.5(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        23.26
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1021627'
_audit_update_record             
;
2014-08-28 deposited with the CCDC.
2015-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H8 Br2 N2 O5'
_chemical_formula_sum            'C14 H8 Br2 N2 O5'
_chemical_formula_weight         444.04

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.188(5)
_cell_length_b                   13.284(7)
_cell_length_c                   14.477(8)
_cell_angle_alpha                68.21(5)
_cell_angle_beta                 81.24(4)
_cell_angle_gamma                75.69(4)
_cell_volume                     1586.2(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2455
_cell_measurement_theta_min      3.8210
_cell_measurement_theta_max      22.2080

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.859
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    5.136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2457
_exptl_absorpt_correction_T_max  0.8209
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_detector_area_resol_mean 10.3712
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11937
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_sigmaI/netI    0.0826
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.27
_diffrn_reflns_theta_max         25.03
_reflns_number_total             5562
_reflns_number_gt                3222
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0499P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5562
_refine_ls_number_parameters     415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1287
_refine_ls_R_factor_gt           0.0654
_refine_ls_wR_factor_ref         0.1365
_refine_ls_wR_factor_gt          0.1146
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6235(7) 0.2504(5) 0.7639(4) 0.0402(15) Uani 1 1 d . . .
C2 C 0.7035(6) 0.1627(5) 0.7218(4) 0.0382(15) Uani 1 1 d . . .
C3 C 0.7860(6) 0.1887(6) 0.6293(4) 0.0493(17) Uani 1 1 d . . .
H3 H 0.7997 0.2608 0.5959 0.059 Uiso 1 1 calc R . .
C4 C 0.8471(7) 0.1087(6) 0.5873(5) 0.0575(19) Uani 1 1 d . . .
H4 H 0.9050 0.1264 0.5272 0.069 Uiso 1 1 calc R . .
C5 C 0.8227(7) 0.0029(6) 0.6340(5) 0.0572(19) Uani 1 1 d . . .
H5 H 0.8591 -0.0508 0.6046 0.069 Uiso 1 1 calc R . .
C6 C 0.7431(7) -0.0217(5) 0.7254(5) 0.0497(17) Uani 1 1 d . . .
C7 C 0.6848(6) 0.0551(5) 0.7711(4) 0.0394(15) Uani 1 1 d . . .
C8 C 0.6046(7) 0.0249(5) 0.8743(5) 0.0435(15) Uani 1 1 d . . .
C10 C 0.6393(7) 0.4171(6) 0.7904(5) 0.0451(16) Uani 1 1 d . . .
C11 C 0.6801(8) 0.4157(7) 0.8802(5) 0.066(2) Uani 1 1 d . . .
C12 C 0.6330(10) 0.5082(9) 0.9067(7) 0.086(3) Uani 1 1 d . . .
H12 H 0.6614 0.5076 0.9659 0.103 Uiso 1 1 calc R . .
C13 C 0.5449(12) 0.6010(8) 0.8469(8) 0.091(3) Uani 1 1 d . . .
H13 H 0.5170 0.6640 0.8646 0.109 Uiso 1 1 calc R . .
C14 C 0.4967(9) 0.6031(6) 0.7613(7) 0.075(2) Uani 1 1 d . . .
H14 H 0.4320 0.6653 0.7226 0.091 Uiso 1 1 calc R . .
C15 C 0.5460(7) 0.5109(6) 0.7336(5) 0.0531(18) Uani 1 1 d . . .
C21 C 0.1250(6) 0.2713(5) 0.7385(4) 0.0380(15) Uani 1 1 d . . .
C22 C 0.1318(6) 0.3548(5) 0.7842(4) 0.0373(14) Uani 1 1 d . . .
C23 C 0.1729(6) 0.3211(5) 0.8809(5) 0.0472(16) Uani 1 1 d . . .
H23 H 0.2031 0.2460 0.9169 0.057 Uiso 1 1 calc R . .
C32 C 0.3237(8) 0.0264(7) 0.5765(6) 0.070(2) Uani 1 1 d . . .
H32 H 0.3683 0.0312 0.5133 0.084 Uiso 1 1 calc R . .
C24 C 0.1695(8) 0.3981(6) 0.9241(5) 0.0614(19) Uani 1 1 d . . .
H24 H 0.1959 0.3751 0.9894 0.074 Uiso 1 1 calc R . .
C25 C 0.1274(8) 0.5078(7) 0.8711(6) 0.063(2) Uani 1 1 d . . .
H25 H 0.1242 0.5602 0.9000 0.075 Uiso 1 1 calc R . .
C26 C 0.0895(7) 0.5410(5) 0.7743(5) 0.0512(17) Uani 1 1 d . . .
C31 C 0.3196(7) 0.1100(6) 0.6133(5) 0.0528(18) Uani 1 1 d . . .
C27 C 0.0882(6) 0.4660(5) 0.7288(4) 0.0394(15) Uani 1 1 d . . .
C28 C 0.0459(8) 0.4968(5) 0.6243(5) 0.0490(17) Uani 1 1 d . . .
C30 C 0.2502(6) 0.1058(5) 0.7061(4) 0.0391(15) Uani 1 1 d . . .
C35 C 0.1822(7) 0.0178(5) 0.7595(5) 0.0483(16) Uani 1 1 d . . .
C33 C 0.2619(9) -0.0631(6) 0.6337(7) 0.075(2) Uani 1 1 d . . .
H33 H 0.2690 -0.1209 0.6105 0.091 Uiso 1 1 calc R . .
C34 C 0.1894(8) -0.0676(6) 0.7252(6) 0.072(2) Uani 1 1 d . . .
H34 H 0.1456 -0.1275 0.7636 0.086 Uiso 1 1 calc R . .
N1 N 0.7014(5) 0.3272(4) 0.7574(4) 0.0444(13) Uani 1 1 d . . .
H1 H 0.7927 0.3209 0.7320 0.053 Uiso 1 1 calc R . .
N2 N 0.7251(8) -0.1367(6) 0.7760(6) 0.082(2) Uani 1 1 d . . .
N21 N 0.2471(5) 0.1905(4) 0.7439(3) 0.0398(12) Uani 1 1 d . . .
H21 H 0.3248 0.1901 0.7706 0.048 Uiso 1 1 calc R . .
N22 N 0.0560(8) 0.6611(6) 0.7158(7) 0.079(2) Uani 1 1 d . . .
O1 O 0.4962(5) 0.2510(4) 0.8009(3) 0.0551(12) Uani 1 1 d . . .
O2 O 0.6666(5) 0.0322(4) 0.9407(3) 0.0635(13) Uani 1 1 d . . .
O3 O 0.4798(5) -0.0024(4) 0.8828(3) 0.0566(12) Uani 1 1 d . . .
H3O H 0.4180 0.0305 0.9146 0.074 Uiso 1 1 calc R . .
O4 O 0.7279(8) -0.1768(5) 0.8648(5) 0.108(2) Uani 1 1 d . . .
O5 O 0.7075(9) -0.1854(5) 0.7225(5) 0.127(3) Uani 1 1 d . . .
O21 O 0.0113(4) 0.2784(4) 0.6996(3) 0.0510(11) Uani 1 1 d . . .
O22 O 0.1428(5) 0.4827(4) 0.5601(3) 0.0595(13) Uani 1 1 d . . .
O23 O -0.0978(5) 0.5310(4) 0.6129(3) 0.0623(13) Uani 1 1 d . . .
H23O H -0.1215 0.5058 0.5748 0.081 Uiso 1 1 calc R . .
O24 O 0.0358(9) 0.7240(5) 0.7634(6) 0.134(3) Uani 1 1 d . . .
O25 O 0.0526(8) 0.6908(5) 0.6289(5) 0.108(2) Uani 1 1 d . . .
Br1 Br 0.47811(10) 0.51347(7) 0.61534(6) 0.0802(3) Uani 1 1 d . . .
Br2 Br 0.79291(10) 0.28691(9) 0.96599(6) 0.0950(3) Uani 1 1 d . . .
Br21 Br 0.40639(9) 0.23167(8) 0.53405(6) 0.0805(3) Uani 1 1 d . . .
Br22 Br 0.07345(9) 0.01214(7) 0.88181(6) 0.0779(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 O1 1.210(6) . ?
C1 N1 1.353(7) . ?
C1 C2 1.495(8) . ?
C2 C7 1.382(8) . ?
C2 C3 1.401(7) . ?
C3 C4 1.376(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.375(8) . ?
C6 N2 1.467(9) . ?
C7 C8 1.517(8) . ?
C8 O2 1.233(7) . ?
C8 O3 1.261(6) . ?
C10 C15 1.374(9) . ?
C10 C11 1.399(9) . ?
C10 N1 1.409(7) . ?
C11 C12 1.371(10) . ?
C11 Br2 1.866(9) . ?
C12 C13 1.361(12) . ?
C12 H12 0.9300 . ?
C13 C14 1.366(12) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(9) . ?
C14 H14 0.9300 . ?
C15 Br1 1.896(7) . ?
C21 O21 1.229(7) . ?
C21 N21 1.336(7) . ?
C21 C22 1.505(8) . ?
C22 C27 1.383(8) . ?
C22 C23 1.384(8) . ?
C23 C24 1.374(8) . ?
C23 H23 0.9300 . ?
C32 C33 1.372(10) . ?
C32 C31 1.389(9) . ?
C32 H32 0.9300 . ?
C24 C25 1.358(10) . ?
C24 H24 0.9300 . ?
C25 C26 1.376(9) . ?
C25 H25 0.9300 . ?
C26 C27 1.387(8) . ?
C26 N22 1.480(9) . ?
C31 C30 1.385(8) . ?
C31 Br21 1.883(7) . ?
C27 C28 1.499(9) . ?
C28 O22 1.219(7) . ?
C28 O23 1.300(7) . ?
C30 C35 1.377(8) . ?
C30 N21 1.415(7) . ?
C35 C34 1.382(9) . ?
C35 Br22 1.880(6) . ?
C33 C34 1.377(10) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
N1 H1 0.8600 . ?
N2 O4 1.198(8) . ?
N2 O5 1.227(8) . ?
N21 H21 0.8600 . ?
N22 O25 1.173(8) . ?
N22 O24 1.232(8) . ?
O3 H3O 0.8200 . ?
O23 H23O 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 123.1(5) . . ?
O1 C1 C2 120.7(5) . . ?
N1 C1 C2 116.2(5) . . ?
C7 C2 C3 119.1(5) . . ?
C7 C2 C1 119.1(5) . . ?
C3 C2 C1 121.6(6) . . ?
C4 C3 C2 120.8(6) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 120.2(6) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 118.3(6) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C7 C6 C5 123.0(6) . . ?
C7 C6 N2 119.7(6) . . ?
C5 C6 N2 117.2(6) . . ?
C6 C7 C2 118.5(5) . . ?
C6 C7 C8 122.2(6) . . ?
C2 C7 C8 119.3(5) . . ?
O2 C8 O3 126.7(6) . . ?
O2 C8 C7 116.5(5) . . ?
O3 C8 C7 116.8(6) . . ?
C15 C10 C11 118.1(6) . . ?
C15 C10 N1 121.8(6) . . ?
C11 C10 N1 120.0(7) . . ?
C12 C11 C10 119.8(8) . . ?
C12 C11 Br2 119.9(7) . . ?
C10 C11 Br2 120.2(6) . . ?
C13 C12 C11 120.5(8) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 121.1(8) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C13 C14 C15 118.5(8) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
C10 C15 C14 121.9(7) . . ?
C10 C15 Br1 119.6(5) . . ?
C14 C15 Br1 118.5(6) . . ?
O21 C21 N21 123.0(5) . . ?
O21 C21 C22 120.5(5) . . ?
N21 C21 C22 116.5(5) . . ?
C27 C22 C23 121.0(5) . . ?
C27 C22 C21 118.1(5) . . ?
C23 C22 C21 120.8(6) . . ?
C24 C23 C22 120.4(6) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C33 C32 C31 119.9(6) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C25 C24 C23 119.8(7) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 119.7(6) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C25 C26 C27 122.3(6) . . ?
C25 C26 N22 118.4(6) . . ?
C27 C26 N22 119.2(7) . . ?
C30 C31 C32 120.8(6) . . ?
C30 C31 Br21 120.0(5) . . ?
C32 C31 Br21 119.2(5) . . ?
C22 C27 C26 116.8(6) . . ?
C22 C27 C28 118.2(5) . . ?
C26 C27 C28 124.9(6) . . ?
O22 C28 O23 125.8(6) . . ?
O22 C28 C27 119.7(6) . . ?
O23 C28 C27 114.4(5) . . ?
C35 C30 C31 118.0(6) . . ?
C35 C30 N21 121.2(5) . . ?
C31 C30 N21 120.8(6) . . ?
C30 C35 C34 121.7(6) . . ?
C30 C35 Br22 120.3(4) . . ?
C34 C35 Br22 118.0(5) . . ?
C32 C33 C34 120.1(7) . . ?
C32 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C33 C34 C35 119.4(7) . . ?
C33 C34 H34 120.3 . . ?
C35 C34 H34 120.3 . . ?
C1 N1 C10 122.8(5) . . ?
C1 N1 H1 118.6 . . ?
C10 N1 H1 118.6 . . ?
O4 N2 O5 124.3(7) . . ?
O4 N2 C6 119.3(7) . . ?
O5 N2 C6 116.4(7) . . ?
C21 N21 C30 120.9(5) . . ?
C21 N21 H21 119.6 . . ?
C30 N21 H21 119.6 . . ?
O25 N22 O24 124.2(8) . . ?
O25 N22 C26 119.5(7) . . ?
O24 N22 C26 116.3(8) . . ?
C8 O3 H3O 109.5 . . ?
C28 O23 H23O 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C7 -39.0(8) . . . . ?
N1 C1 C2 C7 141.2(6) . . . . ?
O1 C1 C2 C3 135.3(6) . . . . ?
N1 C1 C2 C3 -44.5(8) . . . . ?
C7 C2 C3 C4 0.5(9) . . . . ?
C1 C2 C3 C4 -173.8(6) . . . . ?
C2 C3 C4 C5 2.6(10) . . . . ?
C3 C4 C5 C6 -3.3(10) . . . . ?
C4 C5 C6 C7 1.2(10) . . . . ?
C4 C5 C6 N2 -177.0(7) . . . . ?
C5 C6 C7 C2 1.8(10) . . . . ?
N2 C6 C7 C2 180.0(6) . . . . ?
C5 C6 C7 C8 -176.7(6) . . . . ?
N2 C6 C7 C8 1.5(10) . . . . ?
C3 C2 C7 C6 -2.6(9) . . . . ?
C1 C2 C7 C6 171.8(5) . . . . ?
C3 C2 C7 C8 175.9(5) . . . . ?
C1 C2 C7 C8 -9.6(8) . . . . ?
C6 C7 C8 O2 114.1(7) . . . . ?
C2 C7 C8 O2 -64.3(8) . . . . ?
C6 C7 C8 O3 -67.6(8) . . . . ?
C2 C7 C8 O3 113.9(7) . . . . ?
C15 C10 C11 C12 -3.2(9) . . . . ?
N1 C10 C11 C12 172.7(6) . . . . ?
C15 C10 C11 Br2 174.8(4) . . . . ?
N1 C10 C11 Br2 -9.4(8) . . . . ?
C10 C11 C12 C13 1.0(11) . . . . ?
Br2 C11 C12 C13 -177.0(6) . . . . ?
C11 C12 C13 C14 2.5(13) . . . . ?
C12 C13 C14 C15 -3.5(12) . . . . ?
C11 C10 C15 C14 2.1(9) . . . . ?
N1 C10 C15 C14 -173.7(5) . . . . ?
C11 C10 C15 Br1 -176.3(4) . . . . ?
N1 C10 C15 Br1 7.9(8) . . . . ?
C13 C14 C15 C10 1.2(10) . . . . ?
C13 C14 C15 Br1 179.6(5) . . . . ?
O21 C21 C22 C27 -48.7(7) . . . . ?
N21 C21 C22 C27 131.8(6) . . . . ?
O21 C21 C22 C23 127.9(6) . . . . ?
N21 C21 C22 C23 -51.6(7) . . . . ?
C27 C22 C23 C24 0.7(9) . . . . ?
C21 C22 C23 C24 -175.8(5) . . . . ?
C22 C23 C24 C25 -0.9(10) . . . . ?
C23 C24 C25 C26 -0.4(10) . . . . ?
C24 C25 C26 C27 2.0(10) . . . . ?
C24 C25 C26 N22 -175.2(6) . . . . ?
C33 C32 C31 C30 -1.7(11) . . . . ?
C33 C32 C31 Br21 179.6(6) . . . . ?
C23 C22 C27 C26 0.7(8) . . . . ?
C21 C22 C27 C26 177.4(5) . . . . ?
C23 C22 C27 C28 179.7(5) . . . . ?
C21 C22 C27 C28 -3.7(8) . . . . ?
C25 C26 C27 C22 -2.1(9) . . . . ?
N22 C26 C27 C22 175.0(5) . . . . ?
C25 C26 C27 C28 179.1(6) . . . . ?
N22 C26 C27 C28 -3.8(9) . . . . ?
C22 C27 C28 O22 -69.8(8) . . . . ?
C26 C27 C28 O22 109.0(7) . . . . ?
C22 C27 C28 O23 106.1(6) . . . . ?
C26 C27 C28 O23 -75.0(8) . . . . ?
C32 C31 C30 C35 -1.7(9) . . . . ?
Br21 C31 C30 C35 177.0(5) . . . . ?
C32 C31 C30 N21 179.5(6) . . . . ?
Br21 C31 C30 N21 -1.8(8) . . . . ?
C31 C30 C35 C34 3.7(10) . . . . ?
N21 C30 C35 C34 -177.5(6) . . . . ?
C31 C30 C35 Br22 -175.4(5) . . . . ?
N21 C30 C35 Br22 3.4(8) . . . . ?
C31 C32 C33 C34 3.2(12) . . . . ?
C32 C33 C34 C35 -1.2(12) . . . . ?
C30 C35 C34 C33 -2.3(11) . . . . ?
Br22 C35 C34 C33 176.9(6) . . . . ?
O1 C1 N1 C10 -2.1(9) . . . . ?
C2 C1 N1 C10 177.7(6) . . . . ?
C15 C10 N1 C1 -80.2(8) . . . . ?
C11 C10 N1 C1 104.0(7) . . . . ?
C7 C6 N2 O4 -34.8(11) . . . . ?
C5 C6 N2 O4 143.5(7) . . . . ?
C7 C6 N2 O5 145.0(7) . . . . ?
C5 C6 N2 O5 -36.7(10) . . . . ?
O21 C21 N21 C30 -1.6(9) . . . . ?
C22 C21 N21 C30 177.9(5) . . . . ?
C35 C30 N21 C21 -79.2(8) . . . . ?
C31 C30 N21 C21 99.5(6) . . . . ?
C25 C26 N22 O25 165.1(8) . . . . ?
C27 C26 N22 O25 -12.1(10) . . . . ?
C25 C26 N22 O24 -13.7(10) . . . . ?
C27 C26 N22 O24 169.1(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.894
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.078

####################################################################### 
# 
# 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_3cn-new
_database_code_depnum_ccdc_archive 'CCDC 1021628'
_audit_update_record             
;
2015-02-12 deposited with the CCDC.
2015-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 N2 O5'
_chemical_formula_sum            'C15 H10 N2 O5'
_chemical_formula_weight         298.25

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   3.82890(10)
_cell_length_b                   23.3314(7)
_cell_length_c                   7.4554(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.153(3)
_cell_angle_gamma                90.00
_cell_volume                     659.29(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4469
_cell_measurement_theta_min      7.5750
_cell_measurement_theta_max      67.1060

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             308
_exptl_absorpt_coefficient_mu    0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6787
_exptl_absorpt_correction_T_max  0.9437
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Ruby
_diffrn_detector_area_resol_mean 5.1856
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5907
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         7.59
_diffrn_reflns_theta_max         66.60
_reflns_number_total             2304
_reflns_number_gt                2285
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0454P)²+0.0538P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(17)
_refine_ls_number_reflns         2304
_refine_ls_number_parameters     200
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0270
_refine_ls_wR_factor_ref         0.0749
_refine_ls_wR_factor_gt          0.0746
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7038(4) 0.91356(7) 0.66064(19) 0.0433(3) Uani 1 1 d . . .
C2 C 0.7149(4) 0.97393(7) 0.72392(19) 0.0431(3) Uani 1 1 d . . .
C3 C 0.8625(5) 0.99539(8) 0.8898(2) 0.0522(4) Uani 1 1 d . . .
H3 H 0.9779 0.9716 0.9795 0.063 Uiso 1 1 calc R . .
C4 C 0.8321(5) 1.05347(9) 0.9173(2) 0.0612(5) Uani 1 1 d . . .
H4 H 0.9238 1.0691 1.0288 0.073 Uiso 1 1 calc R . .
C5 C 0.6671(5) 1.08911(8) 0.7819(2) 0.0567(4) Uani 1 1 d . . .
H5 H 0.6499 1.1282 0.8028 0.068 Uiso 1 1 calc R . .
C6 C 0.5282(4) 1.06617(7) 0.6154(2) 0.0454(3) Uani 1 1 d . . .
C7 C 0.5465(4) 1.00794(7) 0.58611(19) 0.0402(3) Uani 1 1 d . . .
C8 C 0.3949(4) 0.96948(6) 0.43439(19) 0.0401(3) Uani 1 1 d . . .
C10 C 0.4384(4) 0.86442(6) 0.3727(2) 0.0399(3) Uani 1 1 d . . .
C11 C 0.3026(4) 0.81580(7) 0.4427(2) 0.0463(3) Uani 1 1 d . . .
H11 H 0.2606 0.8151 0.5625 0.056 Uiso 1 1 calc R . .
C12 C 0.2299(4) 0.76838(7) 0.3336(2) 0.0503(4) Uani 1 1 d . . .
H12 H 0.1411 0.7353 0.3804 0.060 Uiso 1 1 calc R . .
C13 C 0.2882(4) 0.76972(6) 0.1552(2) 0.0451(3) Uani 1 1 d . . .
C14 C 0.4259(4) 0.81839(7) 0.0856(2) 0.0457(3) Uani 1 1 d . . .
H14 H 0.4665 0.8193 -0.0345 0.055 Uiso 1 1 calc R . .
C15 C 0.5026(4) 0.86568(6) 0.1958(2) 0.0431(3) Uani 1 1 d . . .
H15 H 0.5977 0.8984 0.1504 0.052 Uiso 1 1 calc R . .
C16 C 0.2446(7) 0.72095(10) -0.1285(3) 0.0762(6) Uani 1 1 d . . .
H16A H 0.1136 0.7521 -0.1897 0.114 Uiso 1 1 calc R . .
H16B H 0.1614 0.6853 -0.1831 0.114 Uiso 1 1 calc R . .
H16C H 0.4905 0.7255 -0.1381 0.114 Uiso 1 1 calc R . .
N1 N 0.5137(3) 0.91430(5) 0.48506(16) 0.0411(3) Uani 1 1 d . . .
N2 N 0.3764(4) 1.10539(6) 0.4715(2) 0.0540(4) Uani 1 1 d . . .
O1 O 0.8319(3) 0.87202(5) 0.73975(15) 0.0591(3) Uani 1 1 d . . .
O2 O 0.1953(3) 0.98085(5) 0.29986(15) 0.0545(3) Uani 1 1 d . . .
O3 O 0.1977(4) 0.72096(5) 0.05707(17) 0.0613(3) Uani 1 1 d . . .
O4 O 0.4350(5) 1.09596(6) 0.31828(18) 0.0739(4) Uani 1 1 d . . .
O5 O 0.2037(5) 1.14570(6) 0.5150(2) 0.0843(5) 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 O1 1.2025(19) . ?
C1 N1 1.4047(19) . ?
C1 C2 1.484(2) . ?
C2 C3 1.379(2) . ?
C2 C7 1.383(2) . ?
C3 C4 1.378(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.379(2) . ?
C6 N2 1.466(2) . ?
C7 C8 1.495(2) . ?
C8 O2 1.2011(17) . ?
C8 N1 1.3994(19) . ?
C10 C15 1.375(2) . ?
C10 C11 1.381(2) . ?
C10 N1 1.4391(19) . ?
C11 C12 1.378(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.380(2) . ?
C12 H12 0.9300 . ?
C13 O3 1.370(2) . ?
C13 C14 1.384(2) . ?
C14 C15 1.382(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 O3 1.420(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N2 O4 1.215(2) . ?
N2 O5 1.220(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
O1 C1 N1 126.04(15) . . ?
O1 C1 C2 128.15(14) . . ?
N1 C1 C2 105.80(12) . . ?
C3 C2 C7 123.13(16) . . ?
C3 C2 C1 128.27(14) . . ?
C7 C2 C1 108.60(13) . . ?
C4 C3 C2 117.24(16) . . ?
C4 C3 H3 121.4 . . ?
C2 C3 H3 121.4 . . ?
C3 C4 C5 121.35(16) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 119.79(18) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C7 C6 C5 120.02(16) . . ?
C7 C6 N2 121.50(14) . . ?
C5 C6 N2 118.43(15) . . ?
C6 C7 C2 118.43(14) . . ?
C6 C7 C8 133.47(14) . . ?
C2 C7 C8 107.92(14) . . ?
O2 C8 N1 124.93(14) . . ?
O2 C8 C7 129.19(14) . . ?
N1 C8 C7 105.74(11) . . ?
C15 C10 C11 120.52(14) . . ?
C15 C10 N1 119.52(13) . . ?
C11 C10 N1 119.96(13) . . ?
C12 C11 C10 119.48(14) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 120.26(14) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
O3 C13 C12 115.64(14) . . ?
O3 C13 C14 124.18(14) . . ?
C12 C13 C14 120.18(14) . . ?
C15 C14 C13 119.46(14) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C10 C15 C14 120.09(13) . . ?
C10 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C8 N1 C1 111.63(12) . . ?
C8 N1 C10 123.78(11) . . ?
C1 N1 C10 124.56(12) . . ?
O4 N2 O5 124.67(16) . . ?
O4 N2 C6 117.91(15) . . ?
O5 N2 C6 117.41(16) . . ?
C13 O3 C16 117.59(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
O1 C1 C2 C3 -2.8(3) . . . . ?
N1 C1 C2 C3 177.97(15) . . . . ?
O1 C1 C2 C7 177.37(16) . . . . ?
N1 C1 C2 C7 -1.89(16) . . . . ?
C7 C2 C3 C4 1.1(3) . . . . ?
C1 C2 C3 C4 -178.72(17) . . . . ?
C2 C3 C4 C5 -1.5(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 C7 1.5(3) . . . . ?
C4 C5 C6 N2 -176.06(17) . . . . ?
C5 C6 C7 C2 -2.0(2) . . . . ?
N2 C6 C7 C2 175.58(14) . . . . ?
C5 C6 C7 C8 172.62(16) . . . . ?
N2 C6 C7 C8 -9.8(3) . . . . ?
C3 C2 C7 C6 0.6(2) . . . . ?
C1 C2 C7 C6 -179.51(13) . . . . ?
C3 C2 C7 C8 -175.25(14) . . . . ?
C1 C2 C7 C8 4.62(17) . . . . ?
C6 C7 C8 O2 -4.7(3) . . . . ?
C2 C7 C8 O2 170.29(15) . . . . ?
C6 C7 C8 N1 179.35(16) . . . . ?
C2 C7 C8 N1 -5.66(16) . . . . ?
C15 C10 C11 C12 -0.3(2) . . . . ?
N1 C10 C11 C12 179.69(13) . . . . ?
C10 C11 C12 C13 -0.8(2) . . . . ?
C11 C12 C13 O3 -178.18(15) . . . . ?
C11 C12 C13 C14 1.1(2) . . . . ?
O3 C13 C14 C15 178.89(15) . . . . ?
C12 C13 C14 C15 -0.4(2) . . . . ?
C11 C10 C15 C14 1.1(2) . . . . ?
N1 C10 C15 C14 -178.93(14) . . . . ?
C13 C14 C15 C10 -0.7(2) . . . . ?
O2 C8 N1 C1 -171.60(15) . . . . ?
C7 C8 N1 C1 4.57(15) . . . . ?
O2 C8 N1 C10 6.3(2) . . . . ?
C7 C8 N1 C10 -177.49(13) . . . . ?
O1 C1 N1 C8 178.87(15) . . . . ?
C2 C1 N1 C8 -1.85(16) . . . . ?
O1 C1 N1 C10 0.9(2) . . . . ?
C2 C1 N1 C10 -179.77(13) . . . . ?
C15 C10 N1 C8 50.84(19) . . . . ?
C11 C10 N1 C8 -129.16(15) . . . . ?
C15 C10 N1 C1 -131.48(15) . . . . ?
C11 C10 N1 C1 48.5(2) . . . . ?
C7 C6 N2 O4 -38.2(2) . . . . ?
C5 C6 N2 O4 139.39(18) . . . . ?
C7 C6 N2 O5 142.79(18) . . . . ?
C5 C6 N2 O5 -39.6(2) . . . . ?
C12 C13 O3 C16 178.40(18) . . . . ?
C14 C13 O3 C16 -0.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        66.60
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1021629'
_audit_update_record             
;
2014-08-28 deposited with the CCDC.
2015-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H6 Br2 N2 O4'
_chemical_formula_sum            'C14 H6 Br2 N2 O4'
_chemical_formula_weight         426.02

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2900 2.4600 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'I 2/a'
_symmetry_space_group_name_Hall  '-I 2ya'

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

_cell_length_a                   14.8231(9)
_cell_length_b                   7.7177(6)
_cell_length_c                   25.714(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.692(7)
_cell_angle_gamma                90.00
_cell_volume                     2915.2(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_theta_min      3.8460
_cell_measurement_theta_max      24.7210

_exptl_crystal_description       plaquet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.941
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1648
_exptl_absorpt_coefficient_mu    5.580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1346
_exptl_absorpt_correction_T_max  0.6638
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3712
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6774
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_av_sigmaI/netI    0.0806
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.29
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2563
_reflns_number_gt                1465
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    dirdif
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0559P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2563
_refine_ls_number_parameters     392
_refine_ls_number_restraints     630
_refine_ls_R_factor_all          0.1050
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1330
_refine_ls_wR_factor_gt          0.1076
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_restrained_S_all      0.866
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1A Br 0.9718(6) 0.3135(9) 0.2676(5) 0.0853(13) Uani 0.50 1 d PDU A 1
Br2A Br 0.7513(5) 0.0479(6) 0.0879(3) 0.0788(9) Uani 0.50 1 d PDU A 1
C10A C 0.8515(18) 0.180(4) 0.1817(5) 0.045(6) Uani 0.50 1 d PDU A 1
C11A C 0.7792(13) 0.076(3) 0.1599(5) 0.044(5) Uani 0.50 1 d PDU A 1
C12A C 0.7325(18) -0.022(4) 0.1936(7) 0.059(6) Uani 0.50 1 d PDU A 1
H12A H 0.6855 -0.0945 0.1793 0.071 Uiso 0.50 1 calc PR A 1
C13A C 0.753(2) -0.014(4) 0.2460(7) 0.057(6) Uani 0.50 1 d PDU A 1
H13A H 0.7208 -0.0787 0.2676 0.068 Uiso 0.50 1 calc PR A 1
C14A C 0.8223(16) 0.089(4) 0.2671(7) 0.055(6) Uani 0.50 1 d PDU A 1
H14A H 0.8377 0.0927 0.3033 0.066 Uiso 0.50 1 calc PR A 1
C15A C 0.8704(10) 0.189(2) 0.2358(6) 0.044(3) Uani 0.50 1 d PDU A 1
O1A O 1.0106(12) 0.0531(15) 0.1284(7) 0.060(3) Uani 0.50 1 d PDU A 1
O2A O 0.8320(12) 0.522(3) 0.1481(11) 0.084(6) Uani 0.50 1 d PDU A 1
N1A N 0.8972(15) 0.288(3) 0.1488(9) 0.048(5) Uani 0.50 1 d PDU A 1
C1A C 0.9803(16) 0.194(2) 0.1254(10) 0.045(5) Uani 0.50 1 d PDU A 1
C2A C 1.0208(14) 0.3440(19) 0.0988(10) 0.043(4) Uani 0.50 1 d PDU A 1
C3A C 1.0940(8) 0.3521(16) 0.0711(7) 0.057(4) Uani 0.50 1 d PDU A 1
H3A H 1.1307 0.2562 0.0676 0.068 Uiso 0.50 1 calc PR A 1
C4A C 1.1099(8) 0.5090(18) 0.0487(6) 0.051(3) Uani 0.50 1 d PDU A 1
C5A C 1.0560(11) 0.6551(17) 0.0545(8) 0.057(6) Uani 0.50 1 d PDU A 1
H5A H 1.0700 0.7599 0.0396 0.068 Uiso 0.50 1 calc PR A 1
C6A C 0.9834(9) 0.6453(17) 0.0817(7) 0.064(4) Uani 0.50 1 d PDU A 1
H6A H 0.9472 0.7412 0.0862 0.077 Uiso 0.50 1 calc PR A 1
C7A C 0.9665(10) 0.486(2) 0.1022(9) 0.046(5) Uani 0.50 1 d PDU A 1
C8A C 0.8947(13) 0.444(3) 0.1351(12) 0.054(5) Uani 0.50 1 d PDU A 1
N2A N 1.1857(6) 0.5186(14) 0.0168(4) 0.075(3) Uani 0.50 1 d PDU . 1
O3A O 1.1959(6) 0.6517(13) -0.0047(4) 0.116(3) Uani 0.50 1 d PDU . 1
O4A O 1.2296(6) 0.3883(14) 0.0132(4) 0.103(3) Uani 0.50 1 d PDU . 1
Br1B Br 0.9819(7) 0.3152(9) 0.2611(5) 0.103(3) Uani 0.50 1 d PDU B 2
Br2B Br 0.7683(6) 0.0402(9) 0.0844(3) 0.117(3) Uani 0.50 1 d PDU B 2
C10B C 0.8660(18) 0.157(4) 0.1791(5) 0.045(6) Uani 0.50 1 d PDU B 2
C11B C 0.7979(13) 0.045(3) 0.1569(5) 0.047(5) Uani 0.50 1 d PDU B 2
C12B C 0.7491(18) -0.046(4) 0.1907(7) 0.067(7) Uani 0.50 1 d PDU B 2
H12B H 0.7012 -0.1178 0.1772 0.080 Uiso 0.50 1 calc PR B 2
C13B C 0.771(2) -0.030(5) 0.2430(8) 0.064(7) Uani 0.50 1 d PDU B 2
H13B H 0.7368 -0.0898 0.2649 0.076 Uiso 0.50 1 calc PR B 2
C14B C 0.8412(16) 0.069(4) 0.2648(7) 0.059(6) Uani 0.50 1 d PDU B 2
H14B H 0.8557 0.0742 0.3011 0.071 Uiso 0.50 1 calc PR B 2
C15B C 0.8909(10) 0.161(2) 0.2329(6) 0.044(3) Uani 0.50 1 d PDU B 2
O1B O 0.7975(9) 0.506(3) 0.1388(11) 0.077(5) Uani 0.50 1 d PDU B 2
O2B O 1.0293(12) 0.1164(19) 0.1417(8) 0.086(5) Uani 0.50 1 d PDU B 2
N1B N 0.9138(14) 0.258(3) 0.1456(9) 0.043(5) Uani 0.50 1 d PDU B 2
C1B C 0.8661(12) 0.441(4) 0.1304(10) 0.047(5) Uani 0.50 1 d PDU B 2
C2B C 0.9363(9) 0.523(3) 0.1001(9) 0.047(4) Uani 0.50 1 d PDU B 2
C3B C 0.9377(8) 0.6771(17) 0.0742(6) 0.060(4) Uani 0.50 1 d PDU B 2
H3B H 0.8899 0.7556 0.0733 0.072 Uiso 0.50 1 calc PR B 2
C4B C 1.0126(9) 0.7117(17) 0.0497(7) 0.063(4) Uani 0.50 1 d PDU B 2
C5B C 1.0848(9) 0.5957(18) 0.0510(7) 0.048(5) Uani 0.50 1 d PDU B 2
H5B H 1.1349 0.6247 0.0346 0.058 Uiso 0.50 1 calc PR B 2
C6B C 1.0831(10) 0.4401(18) 0.0760(7) 0.065(4) Uani 0.50 1 d PDU B 2
H6B H 1.1311 0.3617 0.0775 0.078 Uiso 0.50 1 calc PR B 2
C7B C 1.0055(13) 0.406(2) 0.0991(10) 0.050(5) Uani 0.50 1 d PDU B 2
C8B C 0.9911(15) 0.251(2) 0.1303(12) 0.058(5) Uani 0.50 1 d PDU B 2
N2B N 1.0137(9) 0.8731(13) 0.0191(5) 0.086(3) Uani 0.50 1 d PDU . 2
O3B O 1.0781(6) 0.9110(16) -0.0012(4) 0.104(3) Uani 0.50 1 d PDU . 2
O4B O 0.9451(9) 0.9609(15) 0.0161(5) 0.122(4) Uani 0.50 1 d PDU . 2


_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
Br1A C15A 1.876(10) . ?
Br2A C11A 1.855(11) . ?
C10A C15A 1.385(12) . ?
C10A C11A 1.394(11) . ?
C10A N1A 1.422(11) . ?
C11A C12A 1.399(12) . ?
C12A C13A 1.343(13) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.348(13) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.380(12) . ?
C14A H14A 0.9300 . ?
O1A C1A 1.18(3) . ?
O2A C8A 1.20(3) . ?
N1A C8A 1.26(3) . ?
N1A C1A 1.61(4) . ?
C1A C2A 1.51(2) . ?
C2A C7A 1.372(14) . ?
C2A C3A 1.38(2) . ?
C3A C4A 1.375(18) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.401(16) . ?
C4A N2A 1.479(15) . ?
C5A C6A 1.363(19) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.37(2) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.48(3) . ?
N2A O3A 1.186(10) . ?
N2A O4A 1.208(10) . ?
N2A O4A 1.856(11) 2_755 ?
O3A O3A 1.591(19) 2_755 ?
O4A O4A 0.969(13) 2_755 ?
O4A N2A 1.856(11) 2_755 ?
Br1B C15B 1.872(10) . ?
Br2B C11B 1.856(11) . ?
C10B C15B 1.382(12) . ?
C10B C11B 1.393(11) . ?
C10B N1B 1.419(11) . ?
C11B C12B 1.394(12) . ?
C12B C13B 1.347(13) . ?
C12B H12B 0.9300 . ?
C13B C14B 1.349(13) . ?
C13B H13B 0.9300 . ?
C14B C15B 1.374(12) . ?
C14B H14B 0.9300 . ?
O1B C1B 1.18(3) . ?
O2B C8B 1.20(3) . ?
N1B C8B 1.26(3) . ?
N1B C1B 1.61(4) . ?
C1B C2B 1.52(2) . ?
C2B C3B 1.37(2) . ?
C2B C7B 1.369(14) . ?
C3B C4B 1.375(18) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.392(17) . ?
C4B N2B 1.475(15) . ?
C5B C6B 1.364(18) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.39(2) . ?
C6B H6B 0.9300 . ?
C7B C8B 1.47(3) . ?
N2B O3B 1.184(11) . ?
N2B O4B 1.216(12) . ?
N2B O4B 1.726(13) 5_775 ?
O3B O4B 1.099(12) 5_775 ?
O4B O3B 1.099(12) 5_775 ?
O4B N2B 1.726(13) 5_775 ?

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
C15A C10A C11A 118.4(9) . . ?
C15A C10A N1A 121.1(12) . . ?
C11A C10A N1A 120.1(12) . . ?
C10A C11A C12A 118.6(11) . . ?
C10A C11A Br2A 121.6(10) . . ?
C12A C11A Br2A 119.5(10) . . ?
C13A C12A C11A 121.9(13) . . ?
C13A C12A H12A 119.0 . . ?
C11A C12A H12A 119.0 . . ?
C12A C13A C14A 119.4(13) . . ?
C12A C13A H13A 120.3 . . ?
C14A C13A H13A 120.3 . . ?
C13A C14A C15A 121.2(13) . . ?
C13A C14A H14A 119.4 . . ?
C15A C14A H14A 119.4 . . ?
C14A C15A C10A 120.3(11) . . ?
C14A C15A Br1A 118.5(11) . . ?
C10A C15A Br1A 120.5(10) . . ?
C8A N1A C10A 137(2) . . ?
C8A N1A C1A 108.5(12) . . ?
C10A N1A C1A 114(2) . . ?
O1A C1A C2A 125(2) . . ?
O1A C1A N1A 133.8(18) . . ?
C2A C1A N1A 101.5(15) . . ?
C7A C2A C3A 120.5(18) . . ?
C7A C2A C1A 108(2) . . ?
C3A C2A C1A 131.3(14) . . ?
C4A C3A C2A 116.6(11) . . ?
C4A C3A H3A 121.7 . . ?
C2A C3A H3A 121.7 . . ?
C3A C4A C5A 122.2(14) . . ?
C3A C4A N2A 117.5(10) . . ?
C5A C4A N2A 120.3(13) . . ?
C6A C5A C4A 120.7(14) . . ?
C6A C5A H5A 119.6 . . ?
C4A C5A H5A 119.6 . . ?
C5A C6A C7A 116.3(12) . . ?
C5A C6A H6A 121.8 . . ?
C7A C6A H6A 121.8 . . ?
C6A C7A C2A 123.6(18) . . ?
C6A C7A C8A 126.8(15) . . ?
C2A C7A C8A 109.4(19) . . ?
O2A C8A N1A 114(2) . . ?
O2A C8A C7A 134(2) . . ?
N1A C8A C7A 112(2) . . ?
O3A N2A O4A 125.6(10) . . ?
O3A N2A C4A 117.1(10) . . ?
O4A N2A C4A 117.2(9) . . ?
O3A N2A O4A 98.0(8) . 2_755 ?
C4A N2A O4A 144.1(8) . 2_755 ?
N2A O3A O3A 96.7(8) . 2_755 ?
O4A O4A N2A 116.5(8) 2_755 . ?
N2A O4A N2A 89.0(9) . 2_755 ?
C15B C10B C11B 120.5(9) . . ?
C15B C10B N1B 120.5(12) . . ?
C11B C10B N1B 118.9(12) . . ?
C10B C11B C12B 117.6(11) . . ?
C10B C11B Br2B 119.1(9) . . ?
C12B C11B Br2B 123.0(11) . . ?
C13B C12B C11B 120.1(14) . . ?
C13B C12B H12B 119.9 . . ?
C11B C12B H12B 119.9 . . ?
C12B C13B C14B 122.5(14) . . ?
C12B C13B H13B 118.7 . . ?
C14B C13B H13B 118.7 . . ?
C13B C14B C15B 119.2(14) . . ?
C13B C14B H14B 120.4 . . ?
C15B C14B H14B 120.4 . . ?
C14B C15B C10B 119.6(11) . . ?
C14B C15B Br1B 120.9(11) . . ?
C10B C15B Br1B 118.9(10) . . ?
C8B N1B C10B 136(2) . . ?
C8B N1B C1B 110.4(12) . . ?
C10B N1B C1B 113(2) . . ?
O1B C1B C2B 126(2) . . ?
O1B C1B N1B 134(2) . . ?
C2B C1B N1B 100.4(14) . . ?
C3B C2B C7B 120.4(19) . . ?
C3B C2B C1B 131.9(14) . . ?
C7B C2B C1B 107.6(19) . . ?
C2B C3B C4B 117.2(11) . . ?
C2B C3B H3B 121.4 . . ?
C4B C3B H3B 121.4 . . ?
C3B C4B C5B 122.0(13) . . ?
C3B C4B N2B 118.5(10) . . ?
C5B C4B N2B 119.5(13) . . ?
C6B C5B C4B 121.1(14) . . ?
C6B C5B H5B 119.5 . . ?
C4B C5B H5B 119.5 . . ?
C5B C6B C7B 116.0(12) . . ?
C5B C6B H6B 122.0 . . ?
C7B C6B H6B 122.0 . . ?
C2B C7B C6B 123.2(18) . . ?
C2B C7B C8B 111(2) . . ?
C6B C7B C8B 125.3(15) . . ?
O2B C8B N1B 112(2) . . ?
O2B C8B C7B 137(2) . . ?
N1B C8B C7B 110.0(19) . . ?
O3B N2B O4B 123.4(10) . . ?
O3B N2B C4B 120.7(13) . . ?
O4B N2B C4B 115.8(11) . . ?
O4B N2B O4B 84.5(9) . 5_775 ?
C4B N2B O4B 159.5(13) . 5_775 ?
O4B O3B N2B 98.2(12) 5_775 . ?
O3B O4B N2B 138.0(12) 5_775 . ?
N2B O4B N2B 95.5(9) . 5_775 ?

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
C15A C10A C11A C12A -4(4) . . . . ?
N1A C10A C11A C12A -177(3) . . . . ?
C15A C10A C11A Br2A -178(2) . . . . ?
N1A C10A C11A Br2A 10(4) . . . . ?
C10A C11A C12A C13A 2(4) . . . . ?
Br2A C11A C12A C13A 176(3) . . . . ?
C11A C12A C13A C14A -1(5) . . . . ?
C12A C13A C14A C15A 1(4) . . . . ?
C13A C14A C15A C10A -3(4) . . . . ?
C13A C14A C15A Br1A -175(2) . . . . ?
C11A C10A C15A C14A 4(4) . . . . ?
N1A C10A C15A C14A 177(3) . . . . ?
C11A C10A C15A Br1A 176(2) . . . . ?
N1A C10A C15A Br1A -12(4) . . . . ?
C15A C10A N1A C8A -75(4) . . . . ?
C11A C10A N1A C8A 98(4) . . . . ?
C15A C10A N1A C1A 99(3) . . . . ?
C11A C10A N1A C1A -88(3) . . . . ?
C8A N1A C1A O1A 178(3) . . . . ?
C10A N1A C1A O1A 2(4) . . . . ?
C8A N1A C1A C2A 2(3) . . . . ?
C10A N1A C1A C2A -173.4(17) . . . . ?
O1A C1A C2A C7A 179(2) . . . . ?
N1A C1A C2A C7A -5(2) . . . . ?
O1A C1A C2A C3A 4(4) . . . . ?
N1A C1A C2A C3A -180(2) . . . . ?
C7A C2A C3A C4A 1(3) . . . . ?
C1A C2A C3A C4A 176(2) . . . . ?
C2A C3A C4A C5A 1(3) . . . . ?
C2A C3A C4A N2A -177.4(15) . . . . ?
C3A C4A C5A C6A -2(3) . . . . ?
N2A C4A C5A C6A 176.8(13) . . . . ?
C4A C5A C6A C7A 0(3) . . . . ?
C5A C6A C7A C2A 3(3) . . . . ?
C5A C6A C7A C8A 177(2) . . . . ?
C3A C2A C7A C6A -4(4) . . . . ?
C1A C2A C7A C6A -179.7(19) . . . . ?
C3A C2A C7A C8A -179(2) . . . . ?
C1A C2A C7A C8A 6(3) . . . . ?
C10A N1A C8A O2A -10(5) . . . . ?
C1A N1A C8A O2A 176(2) . . . . ?
C10A N1A C8A C7A 175(2) . . . . ?
C1A N1A C8A C7A 1(3) . . . . ?
C6A C7A C8A O2A 7(5) . . . . ?
C2A C7A C8A O2A -178(3) . . . . ?
C6A C7A C8A N1A -179(2) . . . . ?
C2A C7A C8A N1A -4(3) . . . . ?
C3A C4A N2A O3A 176.0(13) . . . . ?
C5A C4A N2A O3A -3(2) . . . . ?
C3A C4A N2A O4A -1.2(18) . . . . ?
C5A C4A N2A O4A -179.9(16) . . . . ?
C3A C4A N2A O4A 9(2) . . . 2_755 ?
C5A C4A N2A O4A -170.1(16) . . . 2_755 ?
O4A N2A O3A O3A -42.0(16) . . . 2_755 ?
C4A N2A O3A O3A 141.0(10) . . . 2_755 ?
O4A N2A O3A O3A -46.4(10) 2_755 . . 2_755 ?
O3A N2A O4A O4A -9(2) . . . 2_755 ?
C4A N2A O4A O4A 167.6(16) . . . 2_755 ?
O3A N2A O4A N2A 14.1(12) . . . 2_755 ?
C4A N2A O4A N2A -169.0(12) . . . 2_755 ?
O4A N2A O4A N2A 23.4(14) 2_755 . . 2_755 ?
C15B C10B C11B C12B 8(4) . . . . ?
N1B C10B C11B C12B -177(3) . . . . ?
C15B C10B C11B Br2B -179(2) . . . . ?
N1B C10B C11B Br2B -3(4) . . . . ?
C10B C11B C12B C13B -3(4) . . . . ?
Br2B C11B C12B C13B -177(3) . . . . ?
C11B C12B C13B C14B -2(5) . . . . ?
C12B C13B C14B C15B 2(5) . . . . ?
C13B C14B C15B C10B 3(4) . . . . ?
C13B C14B C15B Br1B 174(2) . . . . ?
C11B C10B C15B C14B -8(4) . . . . ?
N1B C10B C15B C14B 177(3) . . . . ?
C11B C10B C15B Br1B -179(2) . . . . ?
N1B C10B C15B Br1B 5(4) . . . . ?
C15B C10B N1B C8B 72(4) . . . . ?
C11B C10B N1B C8B -103(4) . . . . ?
C15B C10B N1B C1B -95(3) . . . . ?
C11B C10B N1B C1B 89(3) . . . . ?
C8B N1B C1B O1B -176(3) . . . . ?
C10B N1B C1B O1B -5(4) . . . . ?
C8B N1B C1B C2B 4(3) . . . . ?
C10B N1B C1B C2B 174.5(17) . . . . ?
O1B C1B C2B C3B -3(4) . . . . ?
N1B C1B C2B C3B 177(2) . . . . ?
O1B C1B C2B C7B 180(3) . . . . ?
N1B C1B C2B C7B 1(2) . . . . ?
C7B C2B C3B C4B -3(3) . . . . ?
C1B C2B C3B C4B -179(2) . . . . ?
C2B C3B C4B C5B 0(3) . . . . ?
C2B C3B C4B N2B 176.7(15) . . . . ?
C3B C4B C5B C6B 1(3) . . . . ?
N2B C4B C5B C6B -175.6(14) . . . . ?
C4B C5B C6B C7B 1(3) . . . . ?
C3B C2B C7B C6B 5(4) . . . . ?
C1B C2B C7B C6B -178(2) . . . . ?
C3B C2B C7B C8B 179(2) . . . . ?
C1B C2B C7B C8B -4(3) . . . . ?
C5B C6B C7B C2B -4(3) . . . . ?
C5B C6B C7B C8B -177(2) . . . . ?
C10B N1B C8B O2B 11(5) . . . . ?
C1B N1B C8B O2B 179(2) . . . . ?
C10B N1B C8B C7B -174(2) . . . . ?
C1B N1B C8B C7B -6(3) . . . . ?
C2B C7B C8B O2B 180(3) . . . . ?
C6B C7B C8B O2B -7(5) . . . . ?
C2B C7B C8B N1B 7(3) . . . . ?
C6B C7B C8B N1B -180(2) . . . . ?
C3B C4B N2B O3B 177.4(13) . . . . ?
C5B C4B N2B O3B -5(2) . . . . ?
C3B C4B N2B O4B -3(2) . . . . ?
C5B C4B N2B O4B 173.9(16) . . . . ?
C3B C4B N2B O4B 169(3) . . . 5_775 ?
C5B C4B N2B O4B -14(4) . . . 5_775 ?
O4B N2B O3B O4B 5(2) . . . 5_775 ?
C4B N2B O3B O4B -175.3(14) . . . 5_775 ?
O3B N2B O4B O3B -8(3) . . . 5_775 ?
C4B N2B O4B O3B 172.6(18) . . . 5_775 ?
O4B N2B O4B O3B -4.6(18) 5_775 . . 5_775 ?
O3B N2B O4B N2B -3.4(13) . . . 5_775 ?
C4B N2B O4B N2B 177.2(14) . . . 5_775 ?
O4B N2B O4B N2B 0.0 5_775 . . 5_775 ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_3dk-new
_database_code_depnum_ccdc_archive 'CCDC 1021630'
_audit_update_record             
;
2015-02-12 deposited with the CCDC.
2015-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H8 Br2 N2 O5'
_chemical_formula_sum            'C14 H8 Br2 N2 O5'
_chemical_formula_weight         444.04

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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   14.0897(3)
_cell_length_b                   4.81830(10)
_cell_length_c                   22.6757(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.607(2)
_cell_angle_gamma                90.00
_cell_volume                     1539.33(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5133
_cell_measurement_theta_min      3.6650
_cell_measurement_theta_max      67.1290

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.916
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    6.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1147
_exptl_absorpt_correction_T_max  0.6420
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Ruby
_diffrn_detector_area_resol_mean 5.1856
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8457
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.68
_diffrn_reflns_theta_max         66.59
_reflns_number_total             2710
_reflns_number_gt                2466
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0637P)²+1.8246P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2710
_refine_ls_number_parameters     216
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1289
_refine_ls_wR_factor_gt          0.1249
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7664(2) 0.5949(6) 0.48529(14) 0.0376(6) Uani 1 1 d . . .
C2 C 0.7334(2) 0.4738(6) 0.54286(13) 0.0373(6) Uani 1 1 d . . .
C3 C 0.7916(3) 0.2874(7) 0.57289(16) 0.0449(8) Uani 1 1 d . . .
H3 H 0.8479 0.2290 0.5558 0.054 Uiso 1 1 calc R . .
C4 C 0.7669(3) 0.1868(8) 0.62814(17) 0.0523(9) Uani 1 1 d . . .
H4 H 0.8050 0.0577 0.6477 0.063 Uiso 1 1 calc R . .
C5 C 0.6855(3) 0.2823(8) 0.65292(16) 0.0517(9) Uani 1 1 d . . .
C6 C 0.6269(3) 0.4732(8) 0.62548(15) 0.0490(8) Uani 1 1 d . . .
H6 H 0.5727 0.5377 0.6440 0.059 Uiso 1 1 calc R . .
C7 C 0.6503(2) 0.5665(7) 0.57000(14) 0.0408(7) Uani 1 1 d . . .
C8 C 0.5824(2) 0.7547(7) 0.53930(16) 0.0448(8) Uani 1 1 d . . .
C10 C 0.8325(2) 0.5001(7) 0.39012(14) 0.0446(8) Uani 1 1 d . . .
C11 C 0.7873(3) 0.6583(9) 0.34657(17) 0.0583(9) Uani 1 1 d . . .
C12 C 0.8360(4) 0.7541(11) 0.2979(2) 0.0790(14) Uani 1 1 d . . .
H12 H 0.8052 0.8631 0.2698 0.095 Uiso 1 1 calc R . .
C13 C 0.9303(4) 0.6866(13) 0.2915(2) 0.0820(15) Uani 1 1 d . . .
H13 H 0.9632 0.7518 0.2590 0.098 Uiso 1 1 calc R . .
C14 C 0.9760(3) 0.5251(11) 0.33239(19) 0.0698(12) Uani 1 1 d . . .
H14 H 1.0393 0.4766 0.3274 0.084 Uiso 1 1 calc R . .
C15 C 0.9270(3) 0.4345(8) 0.38123(16) 0.0509(8) Uani 1 1 d . . .
N1 N 0.7856(2) 0.4128(5) 0.44231(12) 0.0413(6) Uani 1 1 d D . .
N2 N 0.6555(3) 0.1749(9) 0.71061(17) 0.0736(11) Uani 1 1 d . . .
O1 O 0.7786(2) 0.8437(5) 0.48051(11) 0.0563(7) Uani 1 1 d . . .
O2 O 0.5738(2) 0.7456(7) 0.48502(12) 0.0684(8) Uani 1 1 d . . .
O3 O 0.5331(2) 0.9114(7) 0.57261(12) 0.0635(7) Uani 1 1 d D . .
O4 O 0.5961(4) 0.3070(12) 0.7375(2) 0.1259(19) Uani 1 1 d . . .
O5 O 0.6935(3) -0.0383(8) 0.72847(15) 0.0960(12) Uani 1 1 d . . .
Br1 Br 0.65707(4) 0.74225(15) 0.35154(2) 0.0930(3) Uani 1 1 d . . .
Br2 Br 0.99340(3) 0.21594(11) 0.43732(2) 0.0712(2) Uani 1 1 d . . .
H1N H 0.777(3) 0.236(2) 0.447(2) 0.059(13) Uiso 1 1 d D . .
H3O H 0.497(4) 0.998(12) 0.551(2) 0.11(2) Uiso 1 1 d 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 O1 1.216(4) . ?
C1 N1 1.341(4) . ?
C1 C2 1.508(4) . ?
C2 C3 1.390(5) . ?
C2 C7 1.402(5) . ?
C3 C4 1.391(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.363(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(5) . ?
C5 N2 1.473(5) . ?
C6 C7 1.379(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.485(5) . ?
C8 O2 1.236(5) . ?
C8 O3 1.279(4) . ?
C10 C15 1.384(5) . ?
C10 C11 1.396(5) . ?
C10 N1 1.426(4) . ?
C11 C12 1.384(6) . ?
C11 Br1 1.883(4) . ?
C12 C13 1.377(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.366(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(6) . ?
C14 H14 0.9300 . ?
C15 Br2 1.892(4) . ?
N1 H1N 0.8700(11) . ?
N2 O4 1.220(6) . ?
N2 O5 1.225(5) . ?
O3 H3O 0.8200(11) . ?

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
O1 C1 N1 123.4(3) . . ?
O1 C1 C2 120.3(3) . . ?
N1 C1 C2 116.3(3) . . ?
C3 C2 C7 118.8(3) . . ?
C3 C2 C1 119.2(3) . . ?
C7 C2 C1 121.6(3) . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 118.3(3) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C4 C5 C6 122.8(3) . . ?
C4 C5 N2 119.9(4) . . ?
C6 C5 N2 117.3(4) . . ?
C7 C6 C5 118.8(3) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C6 C7 C2 120.4(3) . . ?
C6 C7 C8 117.9(3) . . ?
C2 C7 C8 121.7(3) . . ?
O2 C8 O3 124.1(3) . . ?
O2 C8 C7 120.1(3) . . ?
O3 C8 C7 115.8(3) . . ?
C15 C10 C11 117.0(3) . . ?
C15 C10 N1 120.6(3) . . ?
C11 C10 N1 122.4(3) . . ?
C12 C11 C10 121.3(4) . . ?
C12 C11 Br1 117.9(4) . . ?
C10 C11 Br1 120.8(3) . . ?
C13 C12 C11 119.5(5) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C13 C12 120.8(4) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 119.2(4) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C14 C15 C10 122.3(4) . . ?
C14 C15 Br2 117.8(3) . . ?
C10 C15 Br2 119.9(3) . . ?
C1 N1 C10 120.6(3) . . ?
C1 N1 H1N 121(3) . . ?
C10 N1 H1N 118(3) . . ?
O4 N2 O5 124.9(4) . . ?
O4 N2 C5 117.7(4) . . ?
O5 N2 C5 117.4(4) . . ?
C8 O3 H3O 106(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -117.8(4) . . . . ?
N1 C1 C2 C3 58.8(4) . . . . ?
O1 C1 C2 C7 55.3(4) . . . . ?
N1 C1 C2 C7 -128.1(3) . . . . ?
C7 C2 C3 C4 2.0(5) . . . . ?
C1 C2 C3 C4 175.3(3) . . . . ?
C2 C3 C4 C5 -2.0(5) . . . . ?
C3 C4 C5 C6 0.1(6) . . . . ?
C3 C4 C5 N2 178.3(3) . . . . ?
C4 C5 C6 C7 1.7(6) . . . . ?
N2 C5 C6 C7 -176.5(3) . . . . ?
C5 C6 C7 C2 -1.6(5) . . . . ?
C5 C6 C7 C8 175.3(3) . . . . ?
C3 C2 C7 C6 -0.1(5) . . . . ?
C1 C2 C7 C6 -173.3(3) . . . . ?
C3 C2 C7 C8 -176.9(3) . . . . ?
C1 C2 C7 C8 10.0(5) . . . . ?
C6 C7 C8 O2 -146.8(4) . . . . ?
C2 C7 C8 O2 30.0(5) . . . . ?
C6 C7 C8 O3 30.4(5) . . . . ?
C2 C7 C8 O3 -152.7(3) . . . . ?
C15 C10 C11 C12 -2.5(6) . . . . ?
N1 C10 C11 C12 176.2(4) . . . . ?
C15 C10 C11 Br1 176.3(3) . . . . ?
N1 C10 C11 Br1 -5.0(5) . . . . ?
C10 C11 C12 C13 1.6(8) . . . . ?
Br1 C11 C12 C13 -177.2(4) . . . . ?
C11 C12 C13 C14 0.4(9) . . . . ?
C12 C13 C14 C15 -1.5(8) . . . . ?
C13 C14 C15 C10 0.5(7) . . . . ?
C13 C14 C15 Br2 -179.1(4) . . . . ?
C11 C10 C15 C14 1.4(6) . . . . ?
N1 C10 C15 C14 -177.3(4) . . . . ?
C11 C10 C15 Br2 -179.0(3) . . . . ?
N1 C10 C15 Br2 2.3(4) . . . . ?
O1 C1 N1 C10 7.4(5) . . . . ?
C2 C1 N1 C10 -169.1(3) . . . . ?
C15 C10 N1 C1 105.5(4) . . . . ?
C11 C10 N1 C1 -73.2(4) . . . . ?
C4 C5 N2 O4 163.4(5) . . . . ?
C6 C5 N2 O4 -18.4(7) . . . . ?
C4 C5 N2 O5 -15.3(6) . . . . ?
C6 C5 N2 O5 162.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        66.59
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.679
_refine_diff_density_rms         0.093
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1021631'
_audit_update_record             
;
2014-08-28 deposited with the CCDC.
2015-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 N2 O5'
_chemical_formula_sum            'C15 H10 N2 O5'
_chemical_formula_weight         298.25

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P n'
_symmetry_space_group_name_Hall  'P -2yac'

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

_cell_length_a                   6.9750(12)
_cell_length_b                   3.8760(10)
_cell_length_c                   23.998(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.227(12)
_cell_angle_gamma                90.00
_cell_volume                     648.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    677
_cell_measurement_theta_min      3.4090
_cell_measurement_theta_max      25.4760

_exptl_crystal_description       triangle
_exptl_crystal_colour            yelow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             308
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9546
_exptl_absorpt_correction_T_max  0.9942
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3712
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1900
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_sigmaI/netI    0.0626
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.40
_diffrn_reflns_theta_max         23.25
_reflns_number_total             1462
_reflns_number_gt                1224
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    Sir2004
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1203P)²+0.3323P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_number_reflns         1462
_refine_ls_number_parameters     200
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0724
_refine_ls_wR_factor_ref         0.2172
_refine_ls_wR_factor_gt          0.2049
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.139
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8776(10) 0.346(2) 0.1577(3) 0.039(2) Uani 1 1 d . . .
C2 C 0.7301(10) 0.297(2) 0.2012(3) 0.039(2) Uani 1 1 d . . .
C3 C 0.7292(10) 0.407(2) 0.2563(3) 0.043(2) Uani 1 1 d . . .
H3 H 0.8342 0.5200 0.2723 0.052 Uiso 1 1 calc R . .
C4 C 0.5657(11) 0.341(3) 0.2867(3) 0.047(2) Uani 1 1 d . . .
H4 H 0.5593 0.4106 0.3237 0.057 Uiso 1 1 calc R . .
C5 C 0.4149(12) 0.173(2) 0.2620(4) 0.045(2) Uani 1 1 d . . .
C6 C 0.4142(12) 0.055(2) 0.2065(3) 0.043(2) Uani 1 1 d . . .
H6 H 0.3115 -0.0660 0.1907 0.051 Uiso 1 1 calc R . .
C7 C 0.5731(10) 0.130(2) 0.1777(3) 0.038(2) Uani 1 1 d . . .
C8 C 0.6217(11) 0.048(2) 0.1189(3) 0.041(2) Uani 1 1 d . . .
C10 C 0.8972(10) 0.181(2) 0.0571(3) 0.038(2) Uani 1 1 d . . .
C11 C 1.0743(10) 0.052(3) 0.0541(3) 0.045(2) Uani 1 1 d . . .
H11 H 1.1340 -0.0390 0.0858 0.053 Uiso 1 1 calc R . .
C12 C 1.1722(11) 0.054(2) 0.0027(3) 0.047(2) Uani 1 1 d . . .
H12 H 1.2963 -0.0310 -0.0001 0.057 Uiso 1 1 calc R . .
C13 C 1.0735(9) 0.189(2) -0.0428(3) 0.039(2) Uani 1 1 d . . .
C14 C 0.8927(10) 0.311(2) -0.0397(3) 0.046(2) Uani 1 1 d . . .
H14 H 0.8303 0.3924 -0.0717 0.056 Uiso 1 1 calc R . .
C15 C 0.7986(11) 0.316(2) 0.0109(3) 0.044(2) Uani 1 1 d . . .
H15 H 0.6755 0.4055 0.0137 0.053 Uiso 1 1 calc R . .
C16 C 1.3457(15) 0.077(3) -0.1001(4) 0.071(3) Uani 1 1 d . . .
H16A H 1.3851 0.0982 -0.1380 0.107 Uiso 1 1 calc R . .
H16B H 1.3515 -0.1603 -0.0890 0.107 Uiso 1 1 calc R . .
H16C H 1.4297 0.2114 -0.0764 0.107 Uiso 1 1 calc R . .
N1 N 0.8011(8) 0.1849(19) 0.1099(2) 0.0385(18) Uani 1 1 d . . .
N2 N 0.2443(9) 0.103(2) 0.2948(3) 0.050(2) Uani 1 1 d . . .
O1 O 1.0284(8) 0.481(2) 0.1628(2) 0.0593(17) Uani 1 1 d . . .
O2 O 0.5265(7) -0.1199(17) 0.0855(2) 0.0511(16) Uani 1 1 d . . .
O3 O 1.1553(8) 0.2000(18) -0.0955(2) 0.0596(18) Uani 1 1 d . . .
O4 O 0.1152(10) -0.072(2) 0.2750(3) 0.084(3) Uani 1 1 d . . .
O5 O 0.2364(10) 0.236(3) 0.3408(3) 0.095(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 O1 1.178(9) . ?
C1 N1 1.402(10) . ?
C1 C2 1.494(10) . ?
C2 C7 1.381(11) . ?
C2 C3 1.389(11) . ?
C3 C4 1.391(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.362(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.409(11) . ?
C5 N2 1.465(11) . ?
C6 C7 1.349(12) . ?
C6 H6 0.9300 . ?
C7 C8 1.494(11) . ?
C8 O2 1.218(10) . ?
C8 N1 1.380(10) . ?
C10 C11 1.335(11) . ?
C10 C15 1.394(10) . ?
C10 N1 1.445(9) . ?
C11 C12 1.422(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.351(10) . ?
C13 O3 1.399(9) . ?
C14 C15 1.392(11) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 O3 1.418(12) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N2 O4 1.215(9) . ?
N2 O5 1.221(9) . ?

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
O1 C1 N1 127.3(7) . . ?
O1 C1 C2 127.7(7) . . ?
N1 C1 C2 105.0(6) . . ?
C7 C2 C3 120.8(7) . . ?
C7 C2 C1 109.1(6) . . ?
C3 C2 C1 130.0(7) . . ?
C2 C3 C4 117.6(7) . . ?
C2 C3 H3 121.2 . . ?
C4 C3 H3 121.2 . . ?
C5 C4 C3 119.5(7) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 123.7(7) . . ?
C4 C5 N2 118.8(7) . . ?
C6 C5 N2 117.5(7) . . ?
C7 C6 C5 115.3(8) . . ?
C7 C6 H6 122.4 . . ?
C5 C6 H6 122.4 . . ?
C6 C7 C2 123.0(7) . . ?
C6 C7 C8 130.0(8) . . ?
C2 C7 C8 106.9(6) . . ?
O2 C8 N1 125.9(7) . . ?
O2 C8 C7 127.2(7) . . ?
N1 C8 C7 106.9(7) . . ?
C11 C10 C15 122.5(7) . . ?
C11 C10 N1 119.9(6) . . ?
C15 C10 N1 117.6(6) . . ?
C10 C11 C12 120.5(7) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 116.6(7) . . ?
C13 C12 H12 121.7 . . ?
C11 C12 H12 121.7 . . ?
C14 C13 C12 122.5(7) . . ?
C14 C13 O3 116.0(6) . . ?
C12 C13 O3 121.4(6) . . ?
C13 C14 C15 120.8(7) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C10 C15 C14 117.0(7) . . ?
C10 C15 H15 121.5 . . ?
C14 C15 H15 121.5 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C8 N1 C1 112.0(6) . . ?
C8 N1 C10 124.9(6) . . ?
C1 N1 C10 123.0(6) . . ?
O4 N2 O5 122.7(7) . . ?
O4 N2 C5 119.8(7) . . ?
O5 N2 C5 117.4(7) . . ?
C13 O3 C16 117.4(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C7 179.3(9) . . . . ?
N1 C1 C2 C7 -2.9(9) . . . . ?
O1 C1 C2 C3 3.0(16) . . . . ?
N1 C1 C2 C3 -179.2(8) . . . . ?
C7 C2 C3 C4 0.3(12) . . . . ?
C1 C2 C3 C4 176.2(8) . . . . ?
C2 C3 C4 C5 0.2(13) . . . . ?
C3 C4 C5 C6 0.8(13) . . . . ?
C3 C4 C5 N2 179.5(8) . . . . ?
C4 C5 C6 C7 -2.2(12) . . . . ?
N2 C5 C6 C7 179.0(8) . . . . ?
C5 C6 C7 C2 2.7(12) . . . . ?
C5 C6 C7 C8 -179.8(8) . . . . ?
C3 C2 C7 C6 -1.9(13) . . . . ?
C1 C2 C7 C6 -178.6(8) . . . . ?
C3 C2 C7 C8 -179.9(8) . . . . ?
C1 C2 C7 C8 3.4(9) . . . . ?
C6 C7 C8 O2 -3.4(15) . . . . ?
C2 C7 C8 O2 174.4(9) . . . . ?
C6 C7 C8 N1 179.5(8) . . . . ?
C2 C7 C8 N1 -2.7(9) . . . . ?
C15 C10 C11 C12 1.2(13) . . . . ?
N1 C10 C11 C12 -178.6(9) . . . . ?
C10 C11 C12 C13 -1.1(13) . . . . ?
C11 C12 C13 C14 -0.5(13) . . . . ?
C11 C12 C13 O3 -179.4(8) . . . . ?
C12 C13 C14 C15 2.0(14) . . . . ?
O3 C13 C14 C15 -179.1(9) . . . . ?
C11 C10 C15 C14 0.2(13) . . . . ?
N1 C10 C15 C14 -179.9(9) . . . . ?
C13 C14 C15 C10 -1.8(13) . . . . ?
O2 C8 N1 C1 -176.2(8) . . . . ?
C7 C8 N1 C1 0.9(9) . . . . ?
O2 C8 N1 C10 6.7(13) . . . . ?
C7 C8 N1 C10 -176.1(7) . . . . ?
O1 C1 N1 C8 178.9(9) . . . . ?
C2 C1 N1 C8 1.1(9) . . . . ?
O1 C1 N1 C10 -4.0(13) . . . . ?
C2 C1 N1 C10 178.2(8) . . . . ?
C11 C10 N1 C8 -126.4(9) . . . . ?
C15 C10 N1 C8 53.7(11) . . . . ?
C11 C10 N1 C1 56.9(12) . . . . ?
C15 C10 N1 C1 -123.0(8) . . . . ?
C4 C5 N2 O4 -173.7(9) . . . . ?
C6 C5 N2 O4 5.1(12) . . . . ?
C4 C5 N2 O5 8.7(12) . . . . ?
C6 C5 N2 O5 -172.5(9) . . . . ?
C14 C13 O3 C16 179.3(9) . . . . ?
C12 C13 O3 C16 -1.8(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        23.25
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.078

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1021632'
_audit_update_record             
;
2014-08-28 deposited with the CCDC.
2015-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H5 N O6, C7 H9 N'
_chemical_formula_sum            'C15 H14 N2 O6'
_chemical_formula_weight         318.28

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2d'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   59.519(2)
_cell_length_b                   12.942(5)
_cell_length_c                   7.623(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5872(3)
_cell_formula_units_Z            16
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6725
_cell_measurement_theta_min      3.4300
_cell_measurement_theta_max      23.5990

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2656
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9508
_exptl_absorpt_correction_T_max  0.9944
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_detector_area_resol_mean 10.3712
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20263
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_min       -70
_diffrn_reflns_limit_h_max       70
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2560
_reflns_number_gt                2335
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    Shelxs86
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0510P)²+7.0834P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_number_reflns         2560
_refine_ls_number_parameters     217
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0973
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.002

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.39529(4) 0.0627(2) 0.3931(4) 0.0604(7) Uani 1 1 d . . .
O1 O 0.47390(3) 0.26801(13) -0.0527(2) 0.0332(4) Uani 1 1 d D . .
O2 O 0.48377(3) 0.10220(14) -0.0804(3) 0.0417(5) Uani 1 1 d . . .
O3 O 0.47972(3) 0.09199(16) 0.5106(3) 0.0547(6) Uani 1 1 d . . .
O4 O 0.49109(3) 0.18798(15) 0.2863(2) 0.0387(4) Uani 1 1 d . . .
O5 O 0.39766(4) 0.0490(3) 0.5506(4) 0.0931(9) Uani 1 1 d . . .
O6 O 0.37724(4) 0.0561(2) 0.3173(4) 0.0889(9) Uani 1 1 d . . .
C1 C 0.47191(4) 0.17116(19) -0.0207(3) 0.0297(5) Uani 1 1 d . . .
C2 C 0.45238(4) 0.14176(18) 0.0947(3) 0.0296(6) Uani 1 1 d . . .
C3 C 0.43132(4) 0.1323(2) 0.0157(3) 0.0385(6) Uani 1 1 d . . .
H3 H 0.4299 0.1437 -0.1042 0.046 Uiso 1 1 calc R . .
C4 C 0.41277(4) 0.1065(2) 0.1123(4) 0.0452(7) Uani 1 1 d . . .
H4 H 0.3987 0.1014 0.0596 0.054 Uiso 1 1 calc R . .
C5 C 0.41533(4) 0.0883(2) 0.2888(4) 0.0428(7) Uani 1 1 d . . .
C6 C 0.43578(4) 0.0941(2) 0.3706(4) 0.0386(6) Uani 1 1 d . . .
H6 H 0.4370 0.0798 0.4898 0.046 Uiso 1 1 calc R . .
C7 C 0.45468(4) 0.12160(18) 0.2741(3) 0.0301(5) Uani 1 1 d . . .
C8 C 0.47651(4) 0.13153(19) 0.3685(3) 0.0337(6) Uani 1 1 d . . .
N20 N 0.47622(3) 0.40850(15) 0.2301(3) 0.0346(5) Uani 1 1 d . . .
H3N H 0.4763 0.4734 0.1907 0.080 Uiso 1 1 d . . .
H2N H 0.4888 0.3877 0.2841 0.080 Uiso 1 1 d . . .
C20 C 0.45638(4) 0.38767(18) 0.3380(3) 0.0324(6) Uani 1 1 d . . .
C21 C 0.43560(4) 0.3835(2) 0.2595(4) 0.0416(7) Uani 1 1 d . . .
H21 H 0.4341 0.3959 0.1399 0.050 Uiso 1 1 calc R . .
C22 C 0.41704(5) 0.3608(2) 0.3594(4) 0.0502(8) Uani 1 1 d . . .
H22 H 0.4030 0.3575 0.3059 0.060 Uiso 1 1 calc R . .
C23 C 0.41876(5) 0.3428(2) 0.5379(4) 0.0474(7) Uani 1 1 d . . .
C24 C 0.43989(5) 0.3480(2) 0.6128(4) 0.0471(7) Uani 1 1 d . . .
H24 H 0.4414 0.3358 0.7324 0.056 Uiso 1 1 calc R . .
C25 C 0.45866(4) 0.3705(2) 0.5154(3) 0.0393(6) Uani 1 1 d . . .
H25 H 0.4727 0.3742 0.5685 0.047 Uiso 1 1 calc R . .
C26 C 0.39825(6) 0.3178(3) 0.6463(6) 0.0768(11) Uani 1 1 d . . .
H26A H 0.3854 0.3522 0.5977 0.115 Uiso 1 1 calc R . .
H26B H 0.4006 0.3407 0.7648 0.115 Uiso 1 1 calc R . .
H26C H 0.3958 0.2445 0.6455 0.115 Uiso 1 1 calc R . .
H4O H 0.5042(6) 0.201(3) 0.343(5) 0.075(11) Uiso 1 1 d . . .
H999 H 0.4735(18) 0.325(7) 0.034(13) 0.35(6) Uiso 1 1 d 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
N1 O6 1.223(4) . ?
N1 O5 1.222(4) . ?
N1 C5 1.472(4) . ?
O1 C1 1.282(3) . ?
O1 H999 0.99(2) . ?
O2 C1 1.225(3) . ?
O3 C8 1.214(3) . ?
O4 C8 1.296(3) . ?
O4 H4O 0.91(4) . ?
C1 C2 1.507(3) . ?
C2 C3 1.396(3) . ?
C2 C7 1.399(3) . ?
C3 C4 1.368(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(4) . ?
C6 C7 1.390(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.491(4) . ?
N20 C20 1.464(3) . ?
N20 H3N 0.8920 . ?
N20 H2N 0.8959 . ?
C20 C21 1.375(4) . ?
C20 C25 1.377(3) . ?
C21 C22 1.373(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.384(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.383(4) . ?
C23 C26 1.510(4) . ?
C24 C25 1.373(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 N1 O5 123.8(3) . . ?
O6 N1 C5 118.2(3) . . ?
O5 N1 C5 118.0(3) . . ?
C1 O1 H999 127(7) . . ?
C8 O4 H4O 117(2) . . ?
O2 C1 O1 126.0(2) . . ?
O2 C1 C2 118.5(2) . . ?
O1 C1 C2 115.4(2) . . ?
C3 C2 C7 119.5(2) . . ?
C3 C2 C1 117.6(2) . . ?
C7 C2 C1 122.9(2) . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 118.6(2) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C6 C5 C4 122.3(2) . . ?
C6 C5 N1 119.1(3) . . ?
C4 C5 N1 118.5(3) . . ?
C5 C6 C7 119.5(2) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C6 C7 C2 119.1(2) . . ?
C6 C7 C8 118.2(2) . . ?
C2 C7 C8 122.7(2) . . ?
O3 C8 O4 124.3(2) . . ?
O3 C8 C7 122.1(2) . . ?
O4 C8 C7 113.5(2) . . ?
C20 N20 H3N 111.5 . . ?
C20 N20 H2N 111.1 . . ?
H3N N20 H2N 115.7 . . ?
C21 C20 C25 120.6(2) . . ?
C21 C20 N20 119.2(2) . . ?
C25 C20 N20 120.1(2) . . ?
C22 C21 C20 119.4(3) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C21 C22 C23 121.4(3) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C24 C23 C22 117.7(3) . . ?
C24 C23 C26 121.3(3) . . ?
C22 C23 C26 121.0(3) . . ?
C25 C24 C23 121.8(3) . . ?
C25 C24 H24 119.1 . . ?
C23 C24 H24 119.1 . . ?
C24 C25 C20 119.0(2) . . ?
C24 C25 H25 120.5 . . ?
C20 C25 H25 120.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C3 -95.3(3) . . . . ?
O1 C1 C2 C3 81.9(3) . . . . ?
O2 C1 C2 C7 83.2(3) . . . . ?
O1 C1 C2 C7 -99.6(3) . . . . ?
C7 C2 C3 C4 1.9(4) . . . . ?
C1 C2 C3 C4 -179.6(2) . . . . ?
C2 C3 C4 C5 -1.1(4) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C3 C4 C5 N1 178.8(2) . . . . ?
O6 N1 C5 C6 -178.7(3) . . . . ?
O5 N1 C5 C6 1.1(4) . . . . ?
O6 N1 C5 C4 1.8(4) . . . . ?
O5 N1 C5 C4 -178.3(3) . . . . ?
C4 C5 C6 C7 1.5(4) . . . . ?
N1 C5 C6 C7 -177.9(2) . . . . ?
C5 C6 C7 C2 -0.6(4) . . . . ?
C5 C6 C7 C8 177.5(2) . . . . ?
C3 C2 C7 C6 -1.1(4) . . . . ?
C1 C2 C7 C6 -179.5(2) . . . . ?
C3 C2 C7 C8 -179.0(2) . . . . ?
C1 C2 C7 C8 2.5(4) . . . . ?
C6 C7 C8 O3 19.5(4) . . . . ?
C2 C7 C8 O3 -162.5(2) . . . . ?
C6 C7 C8 O4 -158.7(2) . . . . ?
C2 C7 C8 O4 19.3(3) . . . . ?
C25 C20 C21 C22 -0.7(4) . . . . ?
N20 C20 C21 C22 178.0(2) . . . . ?
C20 C21 C22 C23 0.5(4) . . . . ?
C21 C22 C23 C24 -0.3(5) . . . . ?
C21 C22 C23 C26 -179.9(3) . . . . ?
C22 C23 C24 C25 0.3(4) . . . . ?
C26 C23 C24 C25 179.9(3) . . . . ?
C23 C24 C25 C20 -0.6(4) . . . . ?
C21 C20 C25 C24 0.8(4) . . . . ?
N20 C20 C25 C24 -178.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.033
