# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1510481'
_audit_update_record             
;
2016-10-18 deposited with the CCDC.
2017-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 N2 O4'
_chemical_formula_weight         246.22

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   7.9719(3)
_cell_length_b                   7.8194(3)
_cell_length_c                   38.2632(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2385.15(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2319
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      23.84

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9793
_exptl_absorpt_correction_T_max  0.9813
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11675
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2100
_reflns_number_gt                1273
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1537P)²+1.0396P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refu
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.003(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2100
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0740
_refine_ls_wR_factor_ref         0.2780
_refine_ls_wR_factor_gt          0.2361
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.6411(4) 0.4468(4) 0.05893(10) 0.0697(10) Uani 1 1 d . . .
C2 C 0.6518(4) 0.5219(4) 0.09166(11) 0.0726(10) Uani 1 1 d . . .
C3 C 0.7810(4) 0.4056(5) 0.03943(12) 0.0832(11) Uani 1 1 d . . .
H3 H 0.7689 0.3555 0.0175 0.100 Uiso 1 1 calc R . .
C4 C 0.9371(5) 0.4385(5) 0.05235(14) 0.0968(13) Uani 1 1 d . . .
H4 H 1.0319 0.4110 0.0394 0.116 Uiso 1 1 calc R . .
C5 C 0.8136(5) 0.5540(5) 0.10436(12) 0.0889(12) Uani 1 1 d . . .
H5 H 0.8275 0.6037 0.1262 0.107 Uiso 1 1 calc R . .
C6 C 0.4785(5) 0.5372(4) 0.14630(11) 0.0849(11) Uani 1 1 d . . .
C7 C 0.9531(5) 0.5120(5) 0.08444(15) 0.1021(15) Uani 1 1 d . . .
H7 H 1.0597 0.5346 0.0932 0.123 Uiso 1 1 calc R . .
C8 C 0.5048(5) 0.5731(4) 0.11260(10) 0.0793(11) Uani 1 1 d . . .
H8 H 0.4225 0.6366 0.1013 0.095 Uiso 1 1 calc R . .
C9 C 0.3193(7) 0.5957(5) 0.16274(14) 0.1021(14) Uani 1 1 d . . .
C10 C 0.5919(7) 0.4357(5) 0.16639(12) 0.0992(13) Uani 1 1 d . . .
C11 C 0.1458(12) 0.5804(10) 0.2119(2) 0.214(5) Uani 1 1 d . . .
H11A H 0.1633 0.6788 0.2269 0.256 Uiso 1 1 calc R . .
H11B H 0.0670 0.6148 0.1939 0.256 Uiso 1 1 calc R . .
C12 C 0.0816(16) 0.4731(14) 0.2288(3) 0.287(7) Uani 1 1 d . . .
H12A H 0.0847 0.3668 0.2162 0.430 Uiso 1 1 calc R . .
H12B H -0.0329 0.5041 0.2333 0.430 Uiso 1 1 calc R . .
H12C H 0.1404 0.4609 0.2505 0.430 Uiso 1 1 calc R . .
N1 N 0.4786(4) 0.3979(5) 0.04412(11) 0.0888(10) Uani 1 1 d . . .
N2 N 0.6829(7) 0.3517(6) 0.18192(12) 0.1287(16) Uani 1 1 d . . .
O1 O 0.2190(5) 0.6824(5) 0.14771(9) 0.1239(13) Uani 1 1 d . . .
O2 O 0.3037(5) 0.5422(4) 0.19500(10) 0.1327(14) Uani 1 1 d . . .
O3 O 0.3549(4) 0.4208(8) 0.06052(11) 0.168(2) Uani 1 1 d . . .
O4 O 0.4751(4) 0.3267(4) 0.01633(10) 0.1144(11) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.380(5) . ?
C1 C2 1.386(5) . ?
C1 N1 1.465(4) . ?
C2 C5 1.401(5) . ?
C2 C8 1.475(5) . ?
C3 C4 1.363(6) . ?
C3 H3 0.9300 . ?
C4 C7 1.362(6) . ?
C4 H4 0.9300 . ?
C5 C7 1.388(6) . ?
C5 H5 0.9300 . ?
C6 C8 1.336(5) . ?
C6 C10 1.428(6) . ?
C6 C9 1.489(6) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 O1 1.195(5) . ?
C9 O2 1.309(6) . ?
C10 N2 1.145(6) . ?
C11 C12 1.176(10) . ?
C11 O2 1.447(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N1 O3 1.182(4) . ?
N1 O4 1.200(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C1 C2 122.5(3) . . ?
C3 C1 N1 116.4(3) . . ?
C2 C1 N1 121.0(3) . . ?
C1 C2 C5 116.5(3) . . ?
C1 C2 C8 123.8(3) . . ?
C5 C2 C8 119.6(4) . . ?
C4 C3 C1 119.8(4) . . ?
C4 C3 H3 120.1 . . ?
C1 C3 H3 120.1 . . ?
C3 C4 C7 119.5(4) . . ?
C3 C4 H4 120.3 . . ?
C7 C4 H4 120.3 . . ?
C7 C5 C2 120.3(4) . . ?
C7 C5 H5 119.8 . . ?
C2 C5 H5 119.8 . . ?
C8 C6 C10 122.5(4) . . ?
C8 C6 C9 118.5(4) . . ?
C10 C6 C9 118.9(4) . . ?
C4 C7 C5 121.3(4) . . ?
C4 C7 H7 119.3 . . ?
C5 C7 H7 119.3 . . ?
C6 C8 C2 126.3(4) . . ?
C6 C8 H8 116.9 . . ?
C2 C8 H8 116.9 . . ?
O1 C9 O2 124.9(4) . . ?
O1 C9 C6 122.7(4) . . ?
O2 C9 C6 112.4(4) . . ?
N2 C10 C6 178.5(5) . . ?
C12 C11 O2 118.5(7) . . ?
C12 C11 H11A 107.7 . . ?
O2 C11 H11A 107.7 . . ?
C12 C11 H11B 107.7 . . ?
O2 C11 H11B 107.7 . . ?
H11A C11 H11B 107.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 N1 O4 121.4(4) . . ?
O3 N1 C1 119.5(4) . . ?
O4 N1 C1 118.9(3) . . ?
C9 O2 C11 116.0(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
C3 C1 C2 C5 -0.2(5) . . . . ?
N1 C1 C2 C5 176.1(3) . . . . ?
C3 C1 C2 C8 177.7(3) . . . . ?
N1 C1 C2 C8 -5.9(5) . . . . ?
C2 C1 C3 C4 0.1(6) . . . . ?
N1 C1 C3 C4 -176.4(3) . . . . ?
C1 C3 C4 C7 -0.1(6) . . . . ?
C1 C2 C5 C7 0.3(5) . . . . ?
C8 C2 C5 C7 -177.7(3) . . . . ?
C3 C4 C7 C5 0.1(6) . . . . ?
C2 C5 C7 C4 -0.2(6) . . . . ?
C10 C6 C8 C2 -2.3(6) . . . . ?
C9 C6 C8 C2 -178.2(3) . . . . ?
C1 C2 C8 C6 131.5(4) . . . . ?
C5 C2 C8 C6 -50.6(5) . . . . ?
C8 C6 C9 O1 -4.8(7) . . . . ?
C10 C6 C9 O1 179.2(4) . . . . ?
C8 C6 C9 O2 175.5(4) . . . . ?
C10 C6 C9 O2 -0.5(6) . . . . ?
C8 C6 C10 N2 -48(23) . . . . ?
C9 C6 C10 N2 127(23) . . . . ?
C3 C1 N1 O3 175.6(4) . . . . ?
C2 C1 N1 O3 -1.0(6) . . . . ?
C3 C1 N1 O4 -0.4(5) . . . . ?
C2 C1 N1 O4 -176.9(3) . . . . ?
O1 C9 O2 C11 5.6(8) . . . . ?
C6 C9 O2 C11 -174.7(6) . . . . ?
C12 C11 O2 C9 136.9(12) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1510478'
_audit_update_record             
;
2016-10-18 deposited with the CCDC.
2017-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 N2 O4'
_chemical_formula_weight         402.44

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.4425(3)
_cell_length_b                   7.5450(3)
_cell_length_c                   10.8920(5)
_cell_angle_alpha                100.835(3)
_cell_angle_beta                 96.718(4)
_cell_angle_gamma                113.445(3)
_cell_volume                     538.50(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3338
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      27.13

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             212
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9708
_exptl_absorpt_correction_T_max  0.9832
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7640
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1882
_reflns_number_gt                1554
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0889P)²+0.1803P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refu
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.072(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1882
_refine_ls_number_parameters     162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1699
_refine_ls_wR_factor_gt          0.1559
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 0.2679(5) 0.8453(5) 0.0496(3) 0.1036(10) Uani 1 1 d . . .
H1A H 0.3874 0.9126 0.1158 0.155 Uiso 1 1 calc R . .
H1B H 0.2624 0.9334 -0.0024 0.155 Uiso 1 1 calc R . .
H1C H 0.2691 0.7283 -0.0026 0.155 Uiso 1 1 calc R . .
C2 C 0.0936(4) 0.7871(4) 0.1070(3) 0.0893(8) Uani 1 1 d . . .
H2A H -0.0280 0.7220 0.0407 0.107 Uiso 1 1 calc R . .
H2B H 0.0921 0.9043 0.1609 0.107 Uiso 1 1 calc R . .
C3 C 0.2061(3) 0.7303(3) 0.3034(2) 0.0632(6) Uani 1 1 d . . .
C4 C 0.1943(3) 0.5745(3) 0.37233(19) 0.0549(5) Uani 1 1 d . . .
C5 C 0.0685(3) 0.3722(3) 0.3036(2) 0.0643(6) Uani 1 1 d . . .
C6 C 0.2996(3) 0.6310(3) 0.4922(2) 0.0563(5) Uani 1 1 d . . .
C7 C 0.3171(3) 0.5150(3) 0.58161(19) 0.0557(5) Uani 1 1 d . . .
C8 C 0.4304(4) 0.6210(4) 0.7037(2) 0.0735(7) Uani 1 1 d . . .
C9 C 0.4529(5) 0.5235(5) 0.7955(3) 0.0878(8) Uani 1 1 d . . .
C10 C 0.3631(4) 0.3192(5) 0.7664(3) 0.0838(8) Uani 1 1 d . . .
C11 C 0.2556(4) 0.2115(4) 0.6457(3) 0.0836(8) Uani 1 1 d . . .
C12 C 0.2325(3) 0.3079(4) 0.5536(3) 0.0720(6) Uani 1 1 d . . .
H1 H 0.159(4) 0.227(4) 0.474(3) 0.096(9) Uiso 1 1 d . . .
H2 H 0.203(4) 0.069(4) 0.626(3) 0.097(9) Uiso 1 1 d . . .
H3 H 0.374(4) 0.250(4) 0.827(3) 0.094(8) Uiso 1 1 d . . .
H4 H 0.538(5) 0.612(5) 0.877(3) 0.108(10) Uiso 1 1 d . . .
H5 H 0.487(4) 0.755(4) 0.719(2) 0.086(8) Uiso 1 1 d . . .
H6 H 0.373(3) 0.766(3) 0.5247(19) 0.059(6) Uiso 1 1 d . . .
N1 N -0.0345(4) 0.2108(3) 0.2481(2) 0.0949(8) Uani 1 1 d . . .
O1 O 0.1031(3) 0.6495(2) 0.18363(15) 0.0788(5) Uani 1 1 d . . .
O2 O 0.2968(3) 0.9061(2) 0.35074(16) 0.0847(6) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.451(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.467(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O2 1.196(2) . ?
C3 O1 1.325(3) . ?
C3 C4 1.490(3) . ?
C4 C6 1.336(3) . ?
C4 C5 1.427(3) . ?
C5 N1 1.143(3) . ?
C6 C7 1.453(3) . ?
C6 H6 0.91(2) . ?
C7 C8 1.386(3) . ?
C7 C12 1.387(3) . ?
C8 C9 1.380(4) . ?
C8 H5 0.90(3) . ?
C9 C10 1.367(4) . ?
C9 H4 0.97(3) . ?
C10 C11 1.365(4) . ?
C10 H3 0.93(3) . ?
C11 C12 1.378(3) . ?
C11 H2 0.95(3) . ?
C12 H1 0.92(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 O1 108.5(2) . . ?
C1 C2 H2A 110.0 . . ?
O1 C2 H2A 110.0 . . ?
C1 C2 H2B 110.0 . . ?
O1 C2 H2B 110.0 . . ?
H2A C2 H2B 108.4 . . ?
O2 C3 O1 124.5(2) . . ?
O2 C3 C4 124.0(2) . . ?
O1 C3 C4 111.51(17) . . ?
C6 C4 C5 124.53(18) . . ?
C6 C4 C3 118.99(18) . . ?
C5 C4 C3 116.48(18) . . ?
N1 C5 C4 179.1(2) . . ?
C4 C6 C7 131.2(2) . . ?
C4 C6 H6 115.2(13) . . ?
C7 C6 H6 113.6(13) . . ?
C8 C7 C12 117.8(2) . . ?
C8 C7 C6 117.0(2) . . ?
C12 C7 C6 125.2(2) . . ?
C9 C8 C7 121.0(3) . . ?
C9 C8 H5 122.7(17) . . ?
C7 C8 H5 116.2(17) . . ?
C10 C9 C8 119.9(3) . . ?
C10 C9 H4 125.8(19) . . ?
C8 C9 H4 114(2) . . ?
C11 C10 C9 120.1(2) . . ?
C11 C10 H3 118.2(17) . . ?
C9 C10 H3 121.7(17) . . ?
C10 C11 C12 120.2(3) . . ?
C10 C11 H2 118.5(17) . . ?
C12 C11 H2 121.2(18) . . ?
C11 C12 C7 120.9(3) . . ?
C11 C12 H1 116.0(18) . . ?
C7 C12 H1 123.2(18) . . ?
C3 O1 C2 117.03(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C3 C4 C6 -4.0(3) . . . . ?
O1 C3 C4 C6 176.24(18) . . . . ?
O2 C3 C4 C5 175.9(2) . . . . ?
O1 C3 C4 C5 -3.9(3) . . . . ?
C6 C4 C5 N1 131(16) . . . . ?
C3 C4 C5 N1 -49(16) . . . . ?
C5 C4 C6 C7 0.0(4) . . . . ?
C3 C4 C6 C7 179.88(19) . . . . ?
C4 C6 C7 C8 -175.9(2) . . . . ?
C4 C6 C7 C12 5.3(4) . . . . ?
C12 C7 C8 C9 -2.1(4) . . . . ?
C6 C7 C8 C9 179.0(2) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
C8 C9 C10 C11 1.7(4) . . . . ?
C9 C10 C11 C12 -1.7(4) . . . . ?
C10 C11 C12 C7 -0.2(4) . . . . ?
C8 C7 C12 C11 2.1(4) . . . . ?
C6 C7 C12 C11 -179.2(2) . . . . ?
O2 C3 O1 C2 -3.0(4) . . . . ?
C4 C3 O1 C2 176.84(19) . . . . ?
C1 C2 O1 C3 86.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1510479'
_audit_update_record             
;
2016-10-18 deposited with the CCDC.
2017-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 N2 O6'
_chemical_formula_weight         382.36

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   4.6524(2)
_cell_length_b                   19.8872(8)
_cell_length_c                   21.2306(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.610(3)
_cell_angle_gamma                90.00
_cell_volume                     1930.74(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3101
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      21.88

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9806
_exptl_absorpt_correction_T_max  0.9825
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12338
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.41
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3413
_reflns_number_gt                2295
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0800P)²+0.4902P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refu
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3413
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1608
_refine_ls_wR_factor_gt          0.1382
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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 0.8624(5) 0.89365(11) 0.96205(10) 0.0501(6) Uani 1 1 d . . .
C2 C 0.6421(6) 0.92158(13) 0.90886(11) 0.0566(6) Uani 1 1 d . . .
C3 C 1.0537(5) 0.84235(13) 0.94759(11) 0.0544(6) Uani 1 1 d . . .
C4 C 0.8660(5) 0.91777(13) 1.02138(11) 0.0557(6) Uani 1 1 d . . .
C5 C 1.0446(5) 0.89951(12) 1.08052(11) 0.0556(6) Uani 1 1 d . . .
C6 C 1.0468(6) 0.92278(14) 1.14046(12) 0.0686(7) Uani 1 1 d . . .
H6 H 0.9267 0.9562 1.1520 0.082 Uiso 1 1 calc R . .
C7 C 1.2628(6) 0.88728(15) 1.18195(13) 0.0742(8) Uani 1 1 d . . .
H7 H 1.3156 0.8926 1.2261 0.089 Uiso 1 1 calc R . .
C8 C 1.3774(7) 0.84412(16) 1.14518(12) 0.0786(8) Uani 1 1 d . . .
H8 H 1.5260 0.8138 1.1605 0.094 Uiso 1 1 calc R . .
C9 C 0.4368(7) 0.91487(16) 0.79890(12) 0.0826(9) Uani 1 1 d . . .
H9A H 0.4847 0.9598 0.7864 0.099 Uiso 1 1 calc R . .
H9B H 0.2450 0.9161 0.8107 0.099 Uiso 1 1 calc R . .
C10 C 0.4352(9) 0.86833(18) 0.74570(15) 0.1067(12) Uani 1 1 d . . .
H10A H 0.6290 0.8648 0.7365 0.160 Uiso 1 1 calc R . .
H10B H 0.3046 0.8847 0.7085 0.160 Uiso 1 1 calc R . .
H10C H 0.3709 0.8249 0.7571 0.160 Uiso 1 1 calc R . .
C11 C 0.4981(5) 0.00745(12) 0.60772(10) 0.0534(6) Uani 1 1 d . . .
C12 C 0.4223(6) -0.04534(13) 0.56895(12) 0.0580(6) Uani 1 1 d . . .
C13 C 0.3176(6) 0.06921(13) 0.59698(12) 0.0611(6) Uani 1 1 d . . .
C14 C 0.7452(6) 0.00761(12) 0.65933(12) 0.0584(6) Uani 1 1 d . . .
C15 C 0.5515(5) -0.11000(13) 0.56841(11) 0.0579(6) Uani 1 1 d . . .
C16 C 0.4671(6) -0.16373(14) 0.53051(12) 0.0685(7) Uani 1 1 d . . .
H16 H 0.3051 -0.1660 0.4976 0.082 Uiso 1 1 calc R . .
C17 C 0.6683(7) -0.21514(15) 0.55002(14) 0.0760(8) Uani 1 1 d . . .
H17 H 0.6664 -0.2582 0.5328 0.091 Uiso 1 1 calc R . .
C18 C 0.8641(7) -0.19015(15) 0.59837(15) 0.0772(8) Uani 1 1 d . . .
H18 H 1.0239 -0.2139 0.6203 0.093 Uiso 1 1 calc R . .
C19 C 0.2625(9) 0.18140(17) 0.63121(16) 0.1027(12) Uani 1 1 d . . .
H19A H 0.3821 0.2161 0.6168 0.123 Uiso 1 1 calc R . .
H19B H 0.0866 0.1765 0.5990 0.123 Uiso 1 1 calc R . .
C20 C 0.1870(11) 0.2011(2) 0.68801(19) 0.1418(19) Uani 1 1 d . . .
H20A H 0.0686 0.1670 0.7025 0.213 Uiso 1 1 calc R . .
H20B H 0.0787 0.2424 0.6816 0.213 Uiso 1 1 calc R . .
H20C H 0.3608 0.2078 0.7196 0.213 Uiso 1 1 calc R . .
H1M H 0.251(5) -0.0391(12) 0.5365(11) 0.061(7) Uiso 1 1 d . . .
H2M H 0.729(5) 0.9529(12) 1.0245(10) 0.054(6) Uiso 1 1 d . . .
N1 N 1.2072(5) 0.80141(12) 0.93470(10) 0.0723(6) Uani 1 1 d . . .
N2 N 0.9367(6) 0.00895(12) 0.70115(11) 0.0794(7) Uani 1 1 d . . .
O1 O 0.4723(4) 0.96505(10) 0.91552(8) 0.0755(6) Uani 1 1 d . . .
O2 O 0.6547(4) 0.89198(9) 0.85327(7) 0.0655(5) Uani 1 1 d . . .
O3 O 0.4235(4) 0.11787(9) 0.63744(9) 0.0772(6) Uani 1 1 d . . .
O4 O 0.1010(4) 0.07421(10) 0.55651(9) 0.0794(6) Uani 1 1 d . . .
O5 O 0.7996(4) -0.12553(9) 0.61131(8) 0.0687(5) Uani 1 1 d . . .
O6 O 1.2500(4) 0.85007(9) 1.08263(7) 0.0674(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 C4 1.345(3) . ?
C1 C3 1.424(3) . ?
C1 C2 1.486(3) . ?
C2 O1 1.197(3) . ?
C2 O2 1.330(3) . ?
C3 N1 1.149(3) . ?
C4 C5 1.419(3) . ?
C4 H2M 0.95(2) . ?
C5 C6 1.353(3) . ?
C5 O6 1.366(3) . ?
C6 C7 1.399(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.336(4) . ?
C7 H7 0.9300 . ?
C8 O6 1.356(3) . ?
C8 H8 0.9300 . ?
C9 O2 1.462(3) . ?
C9 C10 1.459(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.341(3) . ?
C11 C14 1.435(3) . ?
C11 C13 1.482(3) . ?
C12 C15 1.420(3) . ?
C12 H1M 0.96(2) . ?
C13 O4 1.202(3) . ?
C13 O3 1.327(3) . ?
C14 N2 1.136(3) . ?
C15 C16 1.352(3) . ?
C15 O5 1.367(3) . ?
C16 C17 1.397(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.337(4) . ?
C17 H17 0.9300 . ?
C18 O5 1.359(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.374(5) . ?
C19 O3 1.462(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C4 C1 C3 123.8(2) . . ?
C4 C1 C2 117.8(2) . . ?
C3 C1 C2 118.4(2) . . ?
O1 C2 O2 124.2(2) . . ?
O1 C2 C1 123.9(2) . . ?
O2 C2 C1 111.8(2) . . ?
N1 C3 C1 178.6(3) . . ?
C1 C4 C5 129.9(2) . . ?
C1 C4 H2M 115.6(14) . . ?
C5 C4 H2M 114.5(13) . . ?
C6 C5 O6 109.4(2) . . ?
C6 C5 C4 130.3(2) . . ?
O6 C5 C4 120.4(2) . . ?
C5 C6 C7 107.4(2) . . ?
C5 C6 H6 126.3 . . ?
C7 C6 H6 126.3 . . ?
C8 C7 C6 105.9(2) . . ?
C8 C7 H7 127.0 . . ?
C6 C7 H7 127.0 . . ?
C7 C8 O6 111.5(3) . . ?
C7 C8 H8 124.2 . . ?
O6 C8 H8 124.2 . . ?
O2 C9 C10 108.5(2) . . ?
O2 C9 H9A 110.0 . . ?
C10 C9 H9A 110.0 . . ?
O2 C9 H9B 110.0 . . ?
C10 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C14 123.6(2) . . ?
C12 C11 C13 118.5(2) . . ?
C14 C11 C13 117.9(2) . . ?
C11 C12 C15 130.5(2) . . ?
C11 C12 H1M 115.4(14) . . ?
C15 C12 H1M 114.0(14) . . ?
O4 C13 O3 124.4(2) . . ?
O4 C13 C11 123.7(2) . . ?
O3 C13 C11 111.9(2) . . ?
N2 C14 C11 178.0(3) . . ?
C16 C15 O5 109.6(2) . . ?
C16 C15 C12 130.1(2) . . ?
O5 C15 C12 120.4(2) . . ?
C15 C16 C17 107.3(2) . . ?
C15 C16 H16 126.4 . . ?
C17 C16 H16 126.4 . . ?
C18 C17 C16 106.3(3) . . ?
C18 C17 H17 126.9 . . ?
C16 C17 H17 126.9 . . ?
C17 C18 O5 111.2(3) . . ?
C17 C18 H18 124.4 . . ?
O5 C18 H18 124.4 . . ?
C20 C19 O3 112.1(3) . . ?
C20 C19 H19A 109.2 . . ?
O3 C19 H19A 109.2 . . ?
C20 C19 H19B 109.2 . . ?
O3 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C2 O2 C9 115.2(2) . . ?
C13 O3 C19 116.6(2) . . ?
C18 O5 C15 105.7(2) . . ?
C8 O6 C5 105.79(19) . . ?

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
C4 C1 C2 O1 1.5(4) . . . . ?
C3 C1 C2 O1 -179.5(2) . . . . ?
C4 C1 C2 O2 -177.8(2) . . . . ?
C3 C1 C2 O2 1.2(3) . . . . ?
C4 C1 C3 N1 -157(11) . . . . ?
C2 C1 C3 N1 24(11) . . . . ?
C3 C1 C4 C5 -0.7(4) . . . . ?
C2 C1 C4 C5 178.3(2) . . . . ?
C1 C4 C5 C6 -178.9(3) . . . . ?
C1 C4 C5 O6 -0.5(4) . . . . ?
O6 C5 C6 C7 0.5(3) . . . . ?
C4 C5 C6 C7 179.1(3) . . . . ?
C5 C6 C7 C8 -0.6(3) . . . . ?
C6 C7 C8 O6 0.5(4) . . . . ?
C14 C11 C12 C15 0.5(4) . . . . ?
C13 C11 C12 C15 -179.4(2) . . . . ?
C12 C11 C13 O4 2.2(4) . . . . ?
C14 C11 C13 O4 -177.7(2) . . . . ?
C12 C11 C13 O3 -178.0(2) . . . . ?
C14 C11 C13 O3 2.1(3) . . . . ?
C12 C11 C14 N2 -148(9) . . . . ?
C13 C11 C14 N2 32(9) . . . . ?
C11 C12 C15 C16 177.3(3) . . . . ?
C11 C12 C15 O5 -2.2(4) . . . . ?
O5 C15 C16 C17 0.0(3) . . . . ?
C12 C15 C16 C17 -179.5(3) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C16 C17 C18 O5 0.3(3) . . . . ?
O1 C2 O2 C9 -1.6(4) . . . . ?
C1 C2 O2 C9 177.7(2) . . . . ?
C10 C9 O2 C2 -167.5(3) . . . . ?
O4 C13 O3 C19 -0.2(4) . . . . ?
C11 C13 O3 C19 180.0(2) . . . . ?
C20 C19 O3 C13 125.7(4) . . . . ?
C17 C18 O5 C15 -0.3(3) . . . . ?
C16 C15 O5 C18 0.1(3) . . . . ?
C12 C15 O5 C18 179.7(2) . . . . ?
C7 C8 O6 C5 -0.1(3) . . . . ?
C6 C5 O6 C8 -0.3(3) . . . . ?
C4 C5 O6 C8 -179.0(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         0.322
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 1510485'
_audit_update_record             
;
2016-10-18 deposited with the CCDC.
2017-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 Br N O2'
_chemical_formula_weight         280.12

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'
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   15.601(14)
_cell_length_b                   5.347(6)
_cell_length_c                   17.88(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 124.97(7)
_cell_angle_gamma                90.00
_cell_volume                     1222(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1077
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      21.03

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    3.348
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5541
_exptl_absorpt_correction_T_max  0.6336
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4165
_diffrn_reflns_av_R_equivalents  0.0894
_diffrn_reflns_av_sigmaI/netI    0.1148
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.59
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1881
_reflns_number_gt                685
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1199P)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    refu
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1881
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1624
_refine_ls_R_factor_gt           0.0763
_refine_ls_wR_factor_ref         0.2275
_refine_ls_wR_factor_gt          0.1872
_refine_ls_goodness_of_fit_ref   0.845
_refine_ls_restrained_S_all      0.845
_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
Br3 Br 0.05659(10) 1.48276(18) 0.18186(11) 0.1098(6) Uani 1 1 d . . .
C1 C 0.8588(12) 0.523(2) 0.4717(13) 0.145(6) Uani 1 1 d . . .
H1A H 0.8128 0.4910 0.4073 0.217 Uiso 1 1 calc R . .
H1B H 0.9119 0.3960 0.5000 0.217 Uiso 1 1 calc R . .
H1C H 0.8909 0.6836 0.4817 0.217 Uiso 1 1 calc R . .
C2 C 0.7995(9) 0.5188(17) 0.5110(9) 0.095(3) Uani 1 1 d . . .
H2A H 0.7699 0.3542 0.5047 0.114 Uiso 1 1 calc R . .
H2B H 0.8440 0.5612 0.5754 0.114 Uiso 1 1 calc R . .
C3 C 0.5748(8) 1.0431(14) 0.3552(7) 0.069(2) Uani 1 1 d . . .
C4 C 0.5523(7) 0.8678(13) 0.4041(6) 0.064(2) Uani 1 1 d . . .
C5 C 0.6317(7) 0.6735(15) 0.4595(6) 0.074(2) Uani 1 1 d . . .
C6 C 0.4621(7) 0.8662(14) 0.3964(6) 0.066(2) Uani 1 1 d . . .
H6 H 0.4585 0.7414 0.4307 0.080 Uiso 1 1 calc R . .
C7 C 0.3669(8) 1.0218(13) 0.3447(7) 0.068(2) Uani 1 1 d . . .
C8 C 0.3573(7) 1.2318(15) 0.2942(6) 0.077(2) Uani 1 1 d . . .
H8 H 0.4133 1.2789 0.2922 0.093 Uiso 1 1 calc R . .
C9 C 0.2655(8) 1.3728(16) 0.2466(7) 0.080(3) Uani 1 1 d . . .
H9 H 0.2609 1.5159 0.2149 0.096 Uiso 1 1 calc R . .
C10 C 0.1820(7) 1.2960(16) 0.2473(7) 0.080(3) Uani 1 1 d . . .
C11 C 0.1891(9) 1.0913(17) 0.2979(8) 0.086(3) Uani 1 1 d . . .
H11 H 0.1329 1.0438 0.2997 0.103 Uiso 1 1 calc R . .
C12 C 0.2833(8) 0.9576(15) 0.3465(7) 0.077(3) Uani 1 1 d . . .
H12 H 0.2892 0.8204 0.3811 0.092 Uiso 1 1 calc R . .
N1 N 0.5970(6) 1.1836(13) 0.3217(6) 0.088(2) Uani 1 1 d . . .
O1 O 0.6210(6) 0.5097(10) 0.5010(5) 0.087(2) Uani 1 1 d . . .
O2 O 0.7178(5) 0.7017(10) 0.4615(4) 0.0812(17) 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
Br3 C10 1.889(9) . ?
C1 C2 1.447(17) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O2 1.439(10) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N1 1.133(9) . ?
C3 C4 1.454(12) . ?
C4 C6 1.333(10) . ?
C4 C5 1.480(12) . ?
C5 O1 1.220(10) . ?
C5 O2 1.331(9) . ?
C6 C7 1.477(12) . ?
C6 H6 0.9300 . ?
C7 C12 1.366(13) . ?
C7 C8 1.394(11) . ?
C8 C9 1.395(12) . ?
C8 H8 0.9300 . ?
C9 C10 1.373(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.383(13) . ?
C11 C12 1.401(14) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 C1 106.1(10) . . ?
O2 C2 H2A 110.5 . . ?
C1 C2 H2A 110.5 . . ?
O2 C2 H2B 110.5 . . ?
C1 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
N1 C3 C4 176.2(12) . . ?
C6 C4 C3 123.1(8) . . ?
C6 C4 C5 119.6(7) . . ?
C3 C4 C5 117.2(7) . . ?
O1 C5 O2 123.6(8) . . ?
O1 C5 C4 123.8(8) . . ?
O2 C5 C4 112.6(7) . . ?
C4 C6 C7 133.2(7) . . ?
C4 C6 H6 113.4 . . ?
C7 C6 H6 113.4 . . ?
C12 C7 C8 117.9(9) . . ?
C12 C7 C6 118.4(8) . . ?
C8 C7 C6 123.7(7) . . ?
C9 C8 C7 121.5(8) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C10 C9 C8 118.7(8) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C9 C10 C11 121.5(9) . . ?
C9 C10 Br3 119.2(7) . . ?
C11 C10 Br3 119.3(7) . . ?
C10 C11 C12 118.1(8) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 H11 120.9 . . ?
C7 C12 C11 122.3(9) . . ?
C7 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C5 O2 C2 117.6(7) . . ?

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
N1 C3 C4 C6 124(13) . . . . ?
N1 C3 C4 C5 -60(13) . . . . ?
C6 C4 C5 O1 -1.2(12) . . . . ?
C3 C4 C5 O1 -177.2(9) . . . . ?
C6 C4 C5 O2 -179.2(7) . . . . ?
C3 C4 C5 O2 4.8(10) . . . . ?
C3 C4 C6 C7 -1.2(14) . . . . ?
C5 C4 C6 C7 -177.0(8) . . . . ?
C4 C6 C7 C12 175.1(9) . . . . ?
C4 C6 C7 C8 -5.2(14) . . . . ?
C12 C7 C8 C9 -0.2(13) . . . . ?
C6 C7 C8 C9 -179.9(8) . . . . ?
C7 C8 C9 C10 -2.3(13) . . . . ?
C8 C9 C10 C11 3.5(13) . . . . ?
C8 C9 C10 Br3 -179.2(6) . . . . ?
C9 C10 C11 C12 -2.1(13) . . . . ?
Br3 C10 C11 C12 -179.4(7) . . . . ?
C8 C7 C12 C11 1.6(14) . . . . ?
C6 C7 C12 C11 -178.7(8) . . . . ?
C10 C11 C12 C7 -0.5(14) . . . . ?
O1 C5 O2 C2 3.9(12) . . . . ?
C4 C5 O2 C2 -178.1(8) . . . . ?
C1 C2 O2 C5 155.6(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.868
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.868
_refine_diff_density_max         0.669
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.122
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1510480'
_audit_update_record             
;
2016-10-18 deposited with the CCDC.
2017-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 N2 O5'
_chemical_formula_weight         329.33

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   P2(1)/n

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                   9.2759(5)
_cell_length_b                   8.5195(4)
_cell_length_c                   21.3359(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.680(3)
_cell_angle_gamma                90.00
_cell_volume                     1682.61(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5171
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      25.87

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             692
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9809
_exptl_absorpt_correction_T_max  0.9828
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12477
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2955
_reflns_number_gt                2365
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0845P)²+1.2263P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refu
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2955
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_ref         0.1831
_refine_ls_wR_factor_gt          0.1709
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 0.6942(3) 0.3520(3) 0.03195(12) 0.0441(6) Uani 1 1 d . . .
C2 C 0.7704(3) 0.2968(3) 0.08445(11) 0.0428(6) Uani 1 1 d . . .
C3 C 0.6933(3) 0.2114(3) 0.13425(11) 0.0407(6) Uani 1 1 d . . .
C4 C 0.5595(2) 0.1325(3) 0.10523(11) 0.0422(6) Uani 1 1 d . . .
C5 C 0.4923(3) 0.1958(3) 0.05145(11) 0.0443(6) Uani 1 1 d . . .
C6 C 0.3659(3) 0.1352(3) 0.02400(13) 0.0540(7) Uani 1 1 d . . .
H6 H 0.3206 0.1829 -0.0112 0.065 Uiso 1 1 calc R . .
C7 C 0.3074(3) 0.0025(4) 0.04950(14) 0.0631(8) Uani 1 1 d . . .
H7 H 0.2220 -0.0397 0.0315 0.076 Uiso 1 1 calc R . .
C8 C 0.3750(3) -0.0669(4) 0.10115(15) 0.0639(8) Uani 1 1 d . . .
H8 H 0.3367 -0.1581 0.1174 0.077 Uiso 1 1 calc R . .
C9 C 0.4995(3) -0.0029(3) 0.12934(13) 0.0531(7) Uani 1 1 d . . .
H9 H 0.5437 -0.0505 0.1648 0.064 Uiso 1 1 calc R . .
C10 C 0.6587(3) 0.3247(3) 0.18857(11) 0.0443(6) Uani 1 1 d . . .
C11 C 0.5462(3) 0.4375(3) 0.16781(12) 0.0500(6) Uani 1 1 d . . .
C12 C 0.6244(3) 0.2407(3) 0.24876(12) 0.0554(7) Uani 1 1 d . . .
C13 C 0.5122(7) 0.2590(7) 0.34530(19) 0.138(2) Uani 1 1 d . . .
H13A H 0.4086 0.2685 0.3481 0.166 Uiso 1 1 calc R . .
H13B H 0.5355 0.1480 0.3452 0.166 Uiso 1 1 calc R . .
C14 C 0.5768(7) 0.3236(9) 0.3946(2) 0.173(3) Uani 1 1 d . . .
H14A H 0.6788 0.3045 0.3948 0.259 Uiso 1 1 calc R . .
H14B H 0.5401 0.2795 0.4318 0.259 Uiso 1 1 calc R . .
H14C H 0.5593 0.4347 0.3938 0.259 Uiso 1 1 calc R . .
C15 C 0.9228(3) 0.3279(3) 0.09271(12) 0.0482(6) Uani 1 1 d . . .
C16 C 1.1341(3) 0.2975(4) 0.16120(15) 0.0682(9) Uani 1 1 d . . .
H16A H 1.1562 0.4088 0.1610 0.082 Uiso 1 1 calc R . .
H16B H 1.1879 0.2464 0.1295 0.082 Uiso 1 1 calc R . .
C17 C 1.1733(4) 0.2311(7) 0.22260(19) 0.1200(19) Uani 1 1 d . . .
H17A H 1.1305 0.2922 0.2543 0.180 Uiso 1 1 calc R . .
H17B H 1.2765 0.2322 0.2299 0.180 Uiso 1 1 calc R . .
H17C H 1.1390 0.1249 0.2241 0.180 Uiso 1 1 calc R . .
H1M H 0.825(3) 0.466(3) -0.0145(13) 0.057(9) Uiso 1 1 d . . .
H3M H 0.756(3) 0.134(3) 0.1542(11) 0.044(7) Uiso 1 1 d . . .
H4M H 0.746(3) 0.382(3) 0.1994(13) 0.059(8) Uiso 1 1 d . . .
N1 N 0.4584(3) 0.5196(3) 0.14798(12) 0.0757(8) Uani 1 1 d . . .
N2 N 0.7410(3) 0.4377(3) -0.01491(11) 0.0594(7) Uani 1 1 d . . .
O1 O 0.6586(4) 0.1098(3) 0.26023(12) 0.1092(10) Uani 1 1 d . . .
O2 O 0.5519(3) 0.3284(3) 0.28559(11) 0.0982(9) Uani 1 1 d . . .
O3 O 0.98065(18) 0.2732(2) 0.14808(8) 0.0569(5) Uani 1 1 d . . .
O4 O 0.9960(2) 0.3966(3) 0.05605(10) 0.0721(7) Uani 1 1 d . . .
O5 O 0.55064(18) 0.3226(2) 0.02114(8) 0.0491(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 N2 1.333(3) . ?
C1 O5 1.360(3) . ?
C1 C2 1.369(3) . ?
C2 C15 1.438(3) . ?
C2 C3 1.506(3) . ?
C3 C4 1.509(3) . ?
C3 C10 1.558(3) . ?
C3 H3M 0.96(3) . ?
C4 C5 1.380(3) . ?
C4 C9 1.393(4) . ?
C5 C6 1.377(3) . ?
C5 O5 1.387(3) . ?
C6 C7 1.380(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.367(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.380(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.466(4) . ?
C10 C12 1.521(4) . ?
C10 H4M 0.96(3) . ?
C11 N1 1.135(3) . ?
C12 O1 1.181(4) . ?
C12 O2 1.302(4) . ?
C13 C14 1.300(6) . ?
C13 O2 1.473(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 O4 1.218(3) . ?
C15 O3 1.348(3) . ?
C16 O3 1.447(3) . ?
C16 C17 1.452(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N2 H1M 0.81(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 O5 109.7(2) . . ?
N2 C1 C2 128.7(2) . . ?
O5 C1 C2 121.6(2) . . ?
C1 C2 C15 119.3(2) . . ?
C1 C2 C3 119.9(2) . . ?
C15 C2 C3 120.7(2) . . ?
C2 C3 C4 109.96(19) . . ?
C2 C3 C10 110.8(2) . . ?
C4 C3 C10 112.23(19) . . ?
C2 C3 H3M 110.2(15) . . ?
C4 C3 H3M 109.5(15) . . ?
C10 C3 H3M 104.0(15) . . ?
C5 C4 C9 117.4(2) . . ?
C5 C4 C3 118.9(2) . . ?
C9 C4 C3 123.7(2) . . ?
C6 C5 C4 122.3(2) . . ?
C6 C5 O5 116.2(2) . . ?
C4 C5 O5 121.5(2) . . ?
C5 C6 C7 119.0(3) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C8 C7 C6 120.0(3) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 120.5(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C4 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C4 C9 H9 119.7 . . ?
C11 C10 C12 112.3(2) . . ?
C11 C10 C3 111.0(2) . . ?
C12 C10 C3 113.6(2) . . ?
C11 C10 H4M 107.9(17) . . ?
C12 C10 H4M 104.8(16) . . ?
C3 C10 H4M 106.6(17) . . ?
N1 C11 C10 175.4(3) . . ?
O1 C12 O2 124.0(3) . . ?
O1 C12 C10 123.4(3) . . ?
O2 C12 C10 112.5(2) . . ?
C14 C13 O2 113.7(5) . . ?
C14 C13 H13A 108.8 . . ?
O2 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
O2 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C15 O3 121.5(2) . . ?
O4 C15 C2 126.4(2) . . ?
O3 C15 C2 112.1(2) . . ?
O3 C16 C17 107.8(3) . . ?
O3 C16 H16A 110.1 . . ?
C17 C16 H16A 110.1 . . ?
O3 C16 H16B 110.1 . . ?
C17 C16 H16B 110.1 . . ?
H16A C16 H16B 108.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1 N2 H1M 121(2) . . ?
C12 O2 C13 117.3(3) . . ?
C15 O3 C16 116.8(2) . . ?
C1 O5 C5 118.14(19) . . ?

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
N2 C1 C2 C15 -1.6(4) . . . . ?
O5 C1 C2 C15 178.4(2) . . . . ?
N2 C1 C2 C3 175.5(3) . . . . ?
O5 C1 C2 C3 -4.6(4) . . . . ?
C1 C2 C3 C4 27.7(3) . . . . ?
C15 C2 C3 C4 -155.3(2) . . . . ?
C1 C2 C3 C10 -97.0(3) . . . . ?
C15 C2 C3 C10 80.0(3) . . . . ?
C2 C3 C4 C5 -27.5(3) . . . . ?
C10 C3 C4 C5 96.4(3) . . . . ?
C2 C3 C4 C9 152.0(2) . . . . ?
C10 C3 C4 C9 -84.2(3) . . . . ?
C9 C4 C5 C6 3.8(4) . . . . ?
C3 C4 C5 C6 -176.7(2) . . . . ?
C9 C4 C5 O5 -174.7(2) . . . . ?
C3 C4 C5 O5 4.8(3) . . . . ?
C4 C5 C6 C7 -2.8(4) . . . . ?
O5 C5 C6 C7 175.7(2) . . . . ?
C5 C6 C7 C8 -0.1(4) . . . . ?
C6 C7 C8 C9 1.9(4) . . . . ?
C7 C8 C9 C4 -0.8(4) . . . . ?
C5 C4 C9 C8 -2.0(4) . . . . ?
C3 C4 C9 C8 178.6(2) . . . . ?
C2 C3 C10 C11 70.2(3) . . . . ?
C4 C3 C10 C11 -53.2(3) . . . . ?
C2 C3 C10 C12 -162.1(2) . . . . ?
C4 C3 C10 C12 74.5(3) . . . . ?
C12 C10 C11 N1 -124(4) . . . . ?
C3 C10 C11 N1 4(4) . . . . ?
C11 C10 C12 O1 147.2(3) . . . . ?
C3 C10 C12 O1 20.2(4) . . . . ?
C11 C10 C12 O2 -32.0(3) . . . . ?
C3 C10 C12 O2 -159.0(3) . . . . ?
C1 C2 C15 O4 -2.4(4) . . . . ?
C3 C2 C15 O4 -179.4(3) . . . . ?
C1 C2 C15 O3 176.7(2) . . . . ?
C3 C2 C15 O3 -0.3(3) . . . . ?
O1 C12 O2 C13 0.6(6) . . . . ?
C10 C12 O2 C13 179.8(3) . . . . ?
C14 C13 O2 C12 113.0(6) . . . . ?
O4 C15 O3 C16 -1.2(4) . . . . ?
C2 C15 O3 C16 179.7(2) . . . . ?
C17 C16 O3 C15 179.8(3) . . . . ?
N2 C1 O5 C5 158.7(2) . . . . ?
C2 C1 O5 C5 -21.3(3) . . . . ?
C6 C5 O5 C1 -157.4(2) . . . . ?
C4 C5 O5 C1 21.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_ECUT50
_database_code_depnum_ccdc_archive 'CCDC 1510477'
_audit_update_record             
;
2016-10-19 deposited with the CCDC.
2017-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H16 In N4 O8'
_chemical_formula_weight         651.27

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'
O O 0.0106 0.0060 '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'
In In -0.7276 1.3100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pnna

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

_cell_length_a                   12.2298(18)
_cell_length_b                   25.203(3)
_cell_length_c                   20.219(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     6232.1(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    9898
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      27.46

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.694
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1300
_exptl_absorpt_coefficient_mu    0.404
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9235
_exptl_absorpt_correction_T_max  0.9308
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      110(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24686
_diffrn_reflns_av_R_equivalents  0.0789
_diffrn_reflns_av_sigmaI/netI    0.0825
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.29
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5373
_reflns_number_gt                3134
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0630P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5373
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1242
_refine_ls_wR_factor_gt          0.1161
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_restrained_S_all      0.928
_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 0.3331(3) 0.06908(13) -0.01454(16) 0.0261(8) Uani 1 1 d . . .
C2 C 0.3828(3) 0.11155(12) 0.02768(16) 0.0235(8) Uani 1 1 d . . .
C3 C 0.3174(3) 0.15023(15) 0.0566(2) 0.0472(11) Uani 1 1 d . . .
H3 H 0.2420 0.1491 0.0505 0.057 Uiso 1 1 calc R . .
C4 C 0.3631(4) 0.19027(16) 0.09415(19) 0.0527(13) Uani 1 1 d . . .
H4 H 0.3193 0.2148 0.1161 0.063 Uiso 1 1 calc R . .
C5 C 0.4784(4) 0.19293(16) 0.09831(18) 0.0463(11) Uani 1 1 d . . .
C6 C 0.5442(3) 0.15530(14) 0.0709(2) 0.0414(10) Uani 1 1 d . . .
H6 H 0.6197 0.1570 0.0758 0.050 Uiso 1 1 calc R . .
C7 C 0.4958(3) 0.11423(14) 0.0353(2) 0.0447(11) Uani 1 1 d . . .
H7 H 0.5396 0.0882 0.0163 0.054 Uiso 1 1 calc R . .
C8 C 0.6845(5) 0.42637(15) 0.3175(2) 0.0470(12) Uani 1 1 d . . .
C9 C 0.6364(4) 0.38557(16) 0.2732(2) 0.0481(11) Uani 1 1 d . . .
C10 C 0.6959(4) 0.34696(16) 0.2467(2) 0.0589(13) Uani 1 1 d . . .
H10 H 0.7709 0.3460 0.2544 0.071 Uiso 1 1 calc R . .
C11 C 0.6476(4) 0.30763(16) 0.2073(2) 0.0601(13) Uani 1 1 d . . .
H11 H 0.6907 0.2813 0.1883 0.072 Uiso 1 1 calc R . .
C12 C 0.5360(4) 0.30790(15) 0.1966(2) 0.0533(12) Uani 1 1 d . . .
C13 C 0.4738(4) 0.34755(17) 0.2214(2) 0.0671(14) Uani 1 1 d . . .
H13 H 0.3998 0.3491 0.2112 0.081 Uiso 1 1 calc R . .
C14 C 0.5214(4) 0.38733(17) 0.2633(2) 0.0638(14) Uani 1 1 d . . .
H14 H 0.4785 0.4133 0.2833 0.077 Uiso 1 1 calc R . .
In1 In 0.2500 0.0000 -0.095931(15) 0.02542(13) Uani 1 2 d S . .
N1 N 0.5365(3) 0.23495(13) 0.13344(18) 0.0533(10) Uani 1 1 d . . .
N2 N 0.4761(3) 0.26839(13) 0.15752(17) 0.0574(10) Uani 1 1 d . . .
O1 O 0.23163(17) 0.06549(8) -0.02050(11) 0.0292(6) Uani 1 1 d . . .
O2 O 0.39536(18) 0.03794(8) -0.04630(11) 0.0305(6) Uani 1 1 d . . .
O3 O 0.6229(2) 0.46338(9) 0.34081(12) 0.0502(8) Uani 1 1 d . . .
O4 O 0.7822(3) 0.42414(12) 0.33133(15) 0.0590(9) 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 1.250(4) . ?
C1 O2 1.268(4) . ?
C1 C2 1.498(4) . ?
C1 In1 2.602(3) . ?
C2 C3 1.390(5) . ?
C2 C7 1.392(5) . ?
C3 C4 1.381(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.415(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.361(5) . ?
C5 N1 1.460(5) . ?
C6 C7 1.393(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O4 1.228(5) . ?
C8 O3 1.288(5) . ?
C8 C9 1.485(5) . ?
C8 In1 2.674(4) 7_666 ?
C9 C10 1.328(5) . ?
C9 C14 1.422(6) . ?
C10 C11 1.403(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.381(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.352(5) . ?
C12 N2 1.467(5) . ?
C13 C14 1.436(5) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
In1 O3 2.215(2) 7_655 ?
In1 O3 2.215(2) 8_565 ?
In1 O2 2.254(2) . ?
In1 O2 2.254(2) 2 ?
In1 O1 2.259(2) . ?
In1 O1 2.259(2) 2 ?
In1 O4 2.444(3) 7_655 ?
In1 O4 2.444(3) 8_565 ?
In1 C1 2.602(3) 2 ?
In1 C8 2.674(4) 7_655 ?
In1 C8 2.674(4) 8_565 ?
N1 N2 1.222(4) . ?
O3 In1 2.215(2) 7_666 ?
O4 In1 2.444(3) 7_666 ?

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 O2 120.2(3) . . ?
O1 C1 C2 120.6(3) . . ?
O2 C1 C2 119.1(3) . . ?
O1 C1 In1 60.20(18) . . ?
O2 C1 In1 60.02(17) . . ?
C2 C1 In1 175.5(2) . . ?
C3 C2 C7 119.4(3) . . ?
C3 C2 C1 120.5(3) . . ?
C7 C2 C1 120.0(3) . . ?
C4 C3 C2 120.7(4) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 118.1(4) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 H4 121.0 . . ?
C6 C5 C4 122.1(4) . . ?
C6 C5 N1 114.6(4) . . ?
C4 C5 N1 123.3(4) . . ?
C5 C6 C7 118.5(4) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C2 C7 C6 121.0(4) . . ?
C2 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
O4 C8 O3 121.2(4) . . ?
O4 C8 C9 119.4(4) . . ?
O3 C8 C9 119.3(5) . . ?
O4 C8 In1 65.9(2) . 7_666 ?
O3 C8 In1 55.48(19) . 7_666 ?
C9 C8 In1 173.7(4) . 7_666 ?
C10 C9 C14 120.5(4) . . ?
C10 C9 C8 122.2(4) . . ?
C14 C9 C8 117.1(4) . . ?
C9 C10 C11 121.1(5) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 120.1(4) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 120.1(4) . . ?
C13 C12 N2 114.9(4) . . ?
C11 C12 N2 125.0(4) . . ?
C12 C13 C14 120.5(5) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C9 C14 C13 117.5(4) . . ?
C9 C14 H14 121.2 . . ?
C13 C14 H14 121.2 . . ?
O3 In1 O3 109.45(14) 7_655 8_565 ?
O3 In1 O2 83.13(10) 7_655 . ?
O3 In1 O2 129.34(9) 8_565 . ?
O3 In1 O2 129.34(9) 7_655 2 ?
O3 In1 O2 83.13(10) 8_565 2 ?
O2 In1 O2 127.13(11) . 2 ?
O3 In1 O1 139.86(9) 7_655 . ?
O3 In1 O1 90.89(8) 8_565 . ?
O2 In1 O1 57.85(8) . . ?
O2 In1 O1 86.04(8) 2 . ?
O3 In1 O1 90.89(8) 7_655 2 ?
O3 In1 O1 139.86(9) 8_565 2 ?
O2 In1 O1 86.04(8) . 2 ?
O2 In1 O1 57.85(8) 2 2 ?
O1 In1 O1 95.05(11) . 2 ?
O3 In1 O4 55.90(10) 7_655 7_655 ?
O3 In1 O4 82.27(9) 8_565 7_655 ?
O2 In1 O4 136.61(10) . 7_655 ?
O2 In1 O4 78.99(10) 2 7_655 ?
O1 In1 O4 164.17(10) . 7_655 ?
O1 In1 O4 81.41(9) 2 7_655 ?
O3 In1 O4 82.27(9) 7_655 8_565 ?
O3 In1 O4 55.90(10) 8_565 8_565 ?
O2 In1 O4 78.99(10) . 8_565 ?
O2 In1 O4 136.61(10) 2 8_565 ?
O1 In1 O4 81.41(9) . 8_565 ?
O1 In1 O4 164.17(10) 2 8_565 ?
O4 In1 O4 106.01(15) 7_655 8_565 ?
O3 In1 C1 111.72(11) 7_655 . ?
O3 In1 C1 111.13(10) 8_565 . ?
O2 In1 C1 29.17(9) . . ?
O2 In1 C1 108.07(10) 2 . ?
O1 In1 C1 28.70(9) . . ?
O1 In1 C1 91.32(8) 2 . ?
O4 In1 C1 165.19(11) 7_655 . ?
O4 In1 C1 78.13(11) 8_565 . ?
O3 In1 C1 111.13(10) 7_655 2 ?
O3 In1 C1 111.72(11) 8_565 2 ?
O2 In1 C1 108.07(10) . 2 ?
O2 In1 C1 29.17(9) 2 2 ?
O1 In1 C1 91.32(8) . 2 ?
O1 In1 C1 28.70(9) 2 2 ?
O4 In1 C1 78.13(11) 7_655 2 ?
O4 In1 C1 165.19(11) 8_565 2 ?
C1 In1 C1 101.55(14) . 2 ?
O3 In1 C8 28.64(12) 7_655 7_655 ?
O3 In1 C8 96.98(12) 8_565 7_655 ?
O2 In1 C8 110.46(13) . 7_655 ?
O2 In1 C8 103.49(12) 2 7_655 ?
O1 In1 C8 168.26(13) . 7_655 ?
O1 In1 C8 84.55(11) 2 7_655 ?
O4 In1 C8 27.30(11) 7_655 7_655 ?
O4 In1 C8 95.79(10) 8_565 7_655 ?
C1 In1 C8 139.59(15) . 7_655 ?
C1 In1 C8 93.82(12) 2 7_655 ?
O3 In1 C8 96.98(12) 7_655 8_565 ?
O3 In1 C8 28.64(12) 8_565 8_565 ?
O2 In1 C8 103.49(12) . 8_565 ?
O2 In1 C8 110.46(13) 2 8_565 ?
O1 In1 C8 84.55(11) . 8_565 ?
O1 In1 C8 168.26(13) 2 8_565 ?
O4 In1 C8 95.79(10) 7_655 8_565 ?
O4 In1 C8 27.30(11) 8_565 8_565 ?
C1 In1 C8 93.82(12) . 8_565 ?
C1 In1 C8 139.59(15) 2 8_565 ?
C8 In1 C8 98.22(18) 7_655 8_565 ?
N2 N1 C5 113.6(4) . . ?
N1 N2 C12 112.4(4) . . ?
C1 O1 In1 91.1(2) . . ?
C1 O2 In1 90.8(2) . . ?
C8 O3 In1 95.9(3) . 7_666 ?
C8 O4 In1 86.8(3) . 7_666 ?

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 -5.2(5) . . . . ?
O2 C1 C2 C3 172.1(3) . . . . ?
In1 C1 C2 C3 94(3) . . . . ?
O1 C1 C2 C7 178.3(3) . . . . ?
O2 C1 C2 C7 -4.4(5) . . . . ?
In1 C1 C2 C7 -82(3) . . . . ?
C7 C2 C3 C4 -1.8(6) . . . . ?
C1 C2 C3 C4 -178.3(4) . . . . ?
C2 C3 C4 C5 4.5(6) . . . . ?
C3 C4 C5 C6 -5.1(7) . . . . ?
C3 C4 C5 N1 176.6(4) . . . . ?
C4 C5 C6 C7 2.8(7) . . . . ?
N1 C5 C6 C7 -178.8(4) . . . . ?
C3 C2 C7 C6 -0.5(6) . . . . ?
C1 C2 C7 C6 176.0(3) . . . . ?
C5 C6 C7 C2 0.1(6) . . . . ?
O4 C8 C9 C10 -1.4(7) . . . . ?
O3 C8 C9 C10 178.8(4) . . . . ?
In1 C8 C9 C10 -148(3) 7_666 . . . ?
O4 C8 C9 C14 174.8(4) . . . . ?
O3 C8 C9 C14 -5.1(6) . . . . ?
In1 C8 C9 C14 28(3) 7_666 . . . ?
C14 C9 C10 C11 1.3(7) . . . . ?
C8 C9 C10 C11 177.3(4) . . . . ?
C9 C10 C11 C12 -1.4(7) . . . . ?
C10 C11 C12 C13 3.3(7) . . . . ?
C10 C11 C12 N2 -178.7(4) . . . . ?
C11 C12 C13 C14 -5.0(7) . . . . ?
N2 C12 C13 C14 176.8(4) . . . . ?
C10 C9 C14 C13 -2.9(7) . . . . ?
C8 C9 C14 C13 -179.1(4) . . . . ?
C12 C13 C14 C9 4.7(7) . . . . ?
O1 C1 In1 O3 170.40(18) . . . 7_655 ?
O2 C1 In1 O3 -12.0(2) . . . 7_655 ?
C2 C1 In1 O3 68(3) . . . 7_655 ?
O1 C1 In1 O3 47.8(2) . . . 8_565 ?
O2 C1 In1 O3 -134.59(18) . . . 8_565 ?
C2 C1 In1 O3 -54(3) . . . 8_565 ?
O1 C1 In1 O2 -177.6(3) . . . . ?
C2 C1 In1 O2 80(3) . . . . ?
O1 C1 In1 O2 -41.6(2) . . . 2 ?
O2 C1 In1 O2 135.92(16) . . . 2 ?
C2 C1 In1 O2 -144(3) . . . 2 ?
O2 C1 In1 O1 177.6(3) . . . . ?
C2 C1 In1 O1 -102(3) . . . . ?
O1 C1 In1 O1 -98.1(2) . . . 2 ?
O2 C1 In1 O1 79.45(18) . . . 2 ?
C2 C1 In1 O1 160(3) . . . 2 ?
O1 C1 In1 O4 -158.3(3) . . . 7_655 ?
O2 C1 In1 O4 19.3(5) . . . 7_655 ?
C2 C1 In1 O4 100(3) . . . 7_655 ?
O1 C1 In1 O4 93.8(2) . . . 8_565 ?
O2 C1 In1 O4 -88.65(18) . . . 8_565 ?
C2 C1 In1 O4 -8(3) . . . 8_565 ?
O1 C1 In1 C1 -71.09(18) . . . 2 ?
O2 C1 In1 C1 106.47(19) . . . 2 ?
C2 C1 In1 C1 -173(3) . . . 2 ?
O1 C1 In1 C8 178.75(18) . . . 7_655 ?
O2 C1 In1 C8 -3.7(3) . . . 7_655 ?
C2 C1 In1 C8 77(3) . . . 7_655 ?
O1 C1 In1 C8 71.3(2) . . . 8_565 ?
O2 C1 In1 C8 -111.1(2) . . . 8_565 ?
C2 C1 In1 C8 -31(3) . . . 8_565 ?
C6 C5 N1 N2 179.8(4) . . . . ?
C4 C5 N1 N2 -1.8(6) . . . . ?
C5 N1 N2 C12 175.8(3) . . . . ?
C13 C12 N2 N1 176.5(4) . . . . ?
C11 C12 N2 N1 -1.5(6) . . . . ?
O2 C1 O1 In1 -2.4(3) . . . . ?
C2 C1 O1 In1 174.9(3) . . . . ?
O3 In1 O1 C1 -13.9(3) 7_655 . . . ?
O3 In1 O1 C1 -136.2(2) 8_565 . . . ?
O2 In1 O1 C1 1.40(18) . . . . ?
O2 In1 O1 C1 140.71(19) 2 . . . ?
O1 In1 O1 C1 83.51(19) 2 . . . ?
O4 In1 O1 C1 159.7(3) 7_655 . . . ?
O4 In1 O1 C1 -80.9(2) 8_565 . . . ?
C1 In1 O1 C1 112.0(2) 2 . . . ?
C8 In1 O1 C1 -4.0(6) 7_655 . . . ?
C8 In1 O1 C1 -108.3(2) 8_565 . . . ?
O1 C1 O2 In1 2.4(3) . . . . ?
C2 C1 O2 In1 -174.9(3) . . . . ?
O3 In1 O2 C1 168.75(19) 7_655 . . . ?
O3 In1 O2 C1 59.2(2) 8_565 . . . ?
O2 In1 O2 C1 -56.06(17) 2 . . . ?
O1 In1 O2 C1 -1.38(17) . . . . ?
O1 In1 O2 C1 -99.88(18) 2 . . . ?
O4 In1 O2 C1 -172.95(18) 7_655 . . . ?
O4 In1 O2 C1 85.32(19) 8_565 . . . ?
C1 In1 O2 C1 -81.2(2) 2 . . . ?
C8 In1 O2 C1 177.45(19) 7_655 . . . ?
C8 In1 O2 C1 73.2(2) 8_565 . . . ?
O4 C8 O3 In1 -4.0(5) . . . 7_666 ?
C9 C8 O3 In1 175.8(3) . . . 7_666 ?
O3 C8 O4 In1 3.7(4) . . . 7_666 ?
C9 C8 O4 In1 -176.2(4) . . . 7_666 ?

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         1.237
_refine_diff_density_min         -1.098
_refine_diff_density_rms         0.080

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.006 0.320 0.060 4126 2248 ' '
_platon_squeeze_details          
;
;
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1510482'
_audit_update_record             
;
2016-10-18 deposited with the CCDC.
2017-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 N2 O4'
_chemical_formula_weight         246.22

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

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

_cell_length_a                   4.0497(19)
_cell_length_b                   10.774(5)
_cell_length_c                   13.882(6)
_cell_angle_alpha                103.934(8)
_cell_angle_beta                 96.959(9)
_cell_angle_gamma                91.161(9)
_cell_volume                     582.8(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1243
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      26.07

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9788
_exptl_absorpt_correction_T_max  0.9809
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6102
_diffrn_reflns_av_R_equivalents  0.3053
_diffrn_reflns_av_sigmaI/netI    0.6399
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.52
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2051
_reflns_number_gt                803
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0702P)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    refu
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2051
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.3788
_refine_ls_R_factor_gt           0.1114
_refine_ls_wR_factor_ref         0.2493
_refine_ls_wR_factor_gt          0.2049
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 -0.1150(16) 0.6768(4) 0.1760(4) 0.0514(15) Uani 1 1 d . . .
C2 C 0.0743(14) 0.7920(3) 0.5450(3) 0.0455(13) Uani 1 1 d . . .
C3 C 0.0077(15) 0.7551(3) 0.2684(3) 0.0489(14) Uani 1 1 d . . .
H3 H 0.1329 0.8302 0.2734 0.059 Uiso 1 1 calc R . .
C4 C 0.0863(14) 0.8021(3) 0.4497(3) 0.0467(14) Uani 1 1 d . . .
C5 C -0.2492(15) 0.6042(4) 0.3432(4) 0.0500(15) Uani 1 1 d . . .
H5 H -0.2987 0.5792 0.3997 0.060 Uiso 1 1 calc R . .
C6 C -0.2939(16) 0.5632(4) 0.1649(4) 0.0556(15) Uani 1 1 d . . .
H6 H -0.3670 0.5113 0.1017 0.067 Uiso 1 1 calc R . .
C7 C 0.2680(15) 0.8861(4) 0.6288(3) 0.0505(14) Uani 1 1 d . . .
C8 C -0.0612(14) 0.7184(3) 0.3548(3) 0.0461(13) Uani 1 1 d . . .
C9 C 0.440(2) 0.9336(4) 0.8044(4) 0.0691(19) Uani 1 1 d . . .
H9A H 0.3195 1.0074 0.8333 0.083 Uiso 1 1 calc R . .
H9B H 0.6463 0.9639 0.7869 0.083 Uiso 1 1 calc R . .
C10 C -0.3618(18) 0.5284(4) 0.2501(4) 0.0609(17) Uani 1 1 d . . .
H10 H -0.4855 0.4526 0.2442 0.073 Uiso 1 1 calc R . .
C11 C -0.1126(15) 0.6932(4) 0.5719(3) 0.0479(13) Uani 1 1 d . . .
C12 C 0.513(3) 0.8558(7) 0.8775(5) 0.113(4) Uani 1 1 d . . .
H12A H 0.3084 0.8181 0.8888 0.169 Uiso 1 1 calc R . .
H12B H 0.6205 0.9092 0.9394 0.169 Uiso 1 1 calc R . .
H12C H 0.6562 0.7893 0.8520 0.169 Uiso 1 1 calc R . .
H1M H 0.260(17) 0.875(5) 0.442(4) 0.076(17) Uiso 1 1 d . . .
N1 N -0.2669(17) 0.6172(4) 0.5954(4) 0.0712(16) Uani 1 1 d . . .
N2 N -0.0417(16) 0.7139(4) 0.0848(3) 0.0661(16) Uani 1 1 d . . .
O1 O 0.4322(13) 0.9754(3) 0.6198(3) 0.0704(13) Uani 1 1 d . . .
O2 O 0.2412(12) 0.8563(3) 0.7157(2) 0.0607(12) Uani 1 1 d . . .
O3 O 0.1240(19) 0.8133(4) 0.0949(3) 0.104(2) Uani 1 1 d . . .
O4 O -0.1434(18) 0.6450(4) 0.0039(3) 0.096(2) 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 C6 1.376(8) . ?
C1 C3 1.383(7) . ?
C1 N2 1.478(6) . ?
C2 C4 1.360(6) . ?
C2 C11 1.440(7) . ?
C2 C7 1.475(7) . ?
C3 C8 1.405(6) . ?
C3 H3 0.9300 . ?
C4 C8 1.457(6) . ?
C4 H1M 1.08(7) . ?
C5 C10 1.371(7) . ?
C5 C8 1.399(7) . ?
C5 H5 0.9300 . ?
C6 C10 1.379(7) . ?
C6 H6 0.9300 . ?
C7 O1 1.199(7) . ?
C7 O2 1.336(5) . ?
C9 O2 1.448(6) . ?
C9 C12 1.471(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10 0.9300 . ?
C11 N1 1.150(7) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N2 O4 1.207(6) . ?
N2 O3 1.221(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C3 122.9(5) . . ?
C6 C1 N2 118.2(5) . . ?
C3 C1 N2 118.9(5) . . ?
C4 C2 C11 124.7(4) . . ?
C4 C2 C7 119.3(4) . . ?
C11 C2 C7 115.9(4) . . ?
C1 C3 C8 118.4(5) . . ?
C1 C3 H3 120.8 . . ?
C8 C3 H3 120.8 . . ?
C2 C4 C8 130.2(4) . . ?
C2 C4 H1M 115(3) . . ?
C8 C4 H1M 114(3) . . ?
C10 C5 C8 121.2(4) . . ?
C10 C5 H5 119.4 . . ?
C8 C5 H5 119.4 . . ?
C1 C6 C10 118.2(5) . . ?
C1 C6 H6 120.9 . . ?
C10 C6 H6 120.9 . . ?
O1 C7 O2 124.8(5) . . ?
O1 C7 C2 124.5(4) . . ?
O2 C7 C2 110.7(4) . . ?
C5 C8 C3 118.5(5) . . ?
C5 C8 C4 125.7(4) . . ?
C3 C8 C4 115.8(4) . . ?
O2 C9 C12 109.2(5) . . ?
O2 C9 H9A 109.8 . . ?
C12 C9 H9A 109.8 . . ?
O2 C9 H9B 109.8 . . ?
C12 C9 H9B 109.8 . . ?
H9A C9 H9B 108.3 . . ?
C5 C10 C6 120.7(5) . . ?
C5 C10 H10 119.6 . . ?
C6 C10 H10 119.6 . . ?
N1 C11 C2 177.8(5) . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O4 N2 O3 122.8(5) . . ?
O4 N2 C1 119.2(5) . . ?
O3 N2 C1 118.0(5) . . ?
C7 O2 C9 117.4(4) . . ?

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
C6 C1 C3 C8 -1.7(8) . . . . ?
N2 C1 C3 C8 -179.5(4) . . . . ?
C11 C2 C4 C8 -3.4(8) . . . . ?
C7 C2 C4 C8 175.5(5) . . . . ?
C3 C1 C6 C10 2.1(8) . . . . ?
N2 C1 C6 C10 179.9(5) . . . . ?
C4 C2 C7 O1 2.3(7) . . . . ?
C11 C2 C7 O1 -178.7(5) . . . . ?
C4 C2 C7 O2 -176.3(4) . . . . ?
C11 C2 C7 O2 2.7(6) . . . . ?
C10 C5 C8 C3 0.7(7) . . . . ?
C10 C5 C8 C4 -176.3(5) . . . . ?
C1 C3 C8 C5 0.3(7) . . . . ?
C1 C3 C8 C4 177.6(4) . . . . ?
C2 C4 C8 C5 -1.2(9) . . . . ?
C2 C4 C8 C3 -178.3(4) . . . . ?
C8 C5 C10 C6 -0.3(8) . . . . ?
C1 C6 C10 C5 -1.0(8) . . . . ?
C4 C2 C11 N1 -126(14) . . . . ?
C7 C2 C11 N1 55(14) . . . . ?
C6 C1 N2 O4 0.9(8) . . . . ?
C3 C1 N2 O4 178.8(6) . . . . ?
C6 C1 N2 O3 -178.3(6) . . . . ?
C3 C1 N2 O3 -0.4(8) . . . . ?
O1 C7 O2 C9 -3.6(7) . . . . ?
C2 C7 O2 C9 174.9(5) . . . . ?
C12 C9 O2 C7 -151.9(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.112
####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 1510483'
_audit_update_record             
;
2016-10-18 deposited with the CCDC.
2017-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 F N O2'
_chemical_formula_weight         219.21

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   6.8919(8)
_cell_length_b                   17.956(3)
_cell_length_c                   9.5863(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.958(9)
_cell_angle_gamma                90.00
_cell_volume                     1179.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2409
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      21.58

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9812
_exptl_absorpt_correction_T_max  0.9831
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8367
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2072
_reflns_number_gt                1318
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1657P)²+0.7143P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refu
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2072
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1229
_refine_ls_R_factor_gt           0.0906
_refine_ls_wR_factor_ref         0.3180
_refine_ls_wR_factor_gt          0.2792
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_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 0.3814(6) 0.5749(2) 0.2146(5) 0.0830(13) Uani 1 1 d . . .
H1 H 0.3447 0.6219 0.1807 0.100 Uiso 1 1 calc R . .
C2 C 0.5417(6) 0.5416(2) 0.1691(5) 0.0798(12) Uani 1 1 d . . .
H2 H 0.6123 0.5668 0.1062 0.096 Uiso 1 1 calc R . .
C3 C 0.2734(6) 0.5411(2) 0.3085(4) 0.0753(11) Uani 1 1 d . . .
C4 C 0.3312(7) 0.4710(3) 0.3543(5) 0.0930(15) Uani 1 1 d . . .
H4 H 0.2602 0.4464 0.4177 0.112 Uiso 1 1 calc R . .
C5 C 0.4919(6) 0.4363(2) 0.3085(5) 0.0857(13) Uani 1 1 d . . .
H5 H 0.5268 0.3889 0.3413 0.103 Uiso 1 1 calc R . .
C6 C 0.6015(5) 0.4711(2) 0.2144(4) 0.0676(10) Uani 1 1 d . . .
C7 C 0.7700(6) 0.4397(2) 0.1570(5) 0.0728(11) Uani 1 1 d . . .
C8 C 0.8642(5) 0.3746(2) 0.1772(4) 0.0702(11) Uani 1 1 d . . .
C9 C 0.8165(6) 0.3188(2) 0.2737(5) 0.0775(12) Uani 1 1 d . . .
C10 C 1.0320(6) 0.3603(2) 0.0956(5) 0.0825(13) Uani 1 1 d . . .
C11 C 1.2825(9) 0.2769(4) 0.0512(9) 0.145(3) Uani 1 1 d . . .
H11A H 1.2405 0.2802 -0.0483 0.174 Uiso 1 1 calc R . .
H11B H 1.3881 0.3122 0.0725 0.174 Uiso 1 1 calc R . .
C12 C 1.3451(13) 0.2109(4) 0.0805(12) 0.197(5) Uani 1 1 d . . .
H12A H 1.2363 0.1783 0.0884 0.296 Uiso 1 1 calc R . .
H12B H 1.4272 0.2115 0.1677 0.296 Uiso 1 1 calc R . .
H12C H 1.4184 0.1934 0.0072 0.296 Uiso 1 1 calc R . .
F1 F 0.0956(8) 0.5789(3) 0.3598(6) 0.196(2) Uani 1 1 d . . .
H1M H 0.809(6) 0.469(2) 0.092(4) 0.077(12) Uiso 1 1 d . . .
N1 N 0.7775(6) 0.2735(2) 0.3502(5) 0.1033(14) Uani 1 1 d . . .
O1 O 1.0813(5) 0.40045(19) 0.0066(4) 0.1118(13) Uani 1 1 d . . .
O2 O 1.1193(5) 0.29694(18) 0.1308(4) 0.1021(12) 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 C2 1.367(5) . ?
C1 C3 1.369(6) . ?
C2 C6 1.387(5) . ?
C3 C4 1.379(6) . ?
C3 F1 1.526(6) . ?
C4 C5 1.382(5) . ?
C5 C6 1.385(5) . ?
C6 C7 1.450(5) . ?
C7 C8 1.341(5) . ?
C8 C9 1.426(6) . ?
C8 C10 1.484(5) . ?
C9 N1 1.146(5) . ?
C10 O1 1.193(5) . ?
C10 O2 1.314(5) . ?
C11 C12 1.283(9) . ?
C11 O2 1.468(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C3 121.9(4) . . ?
C1 C2 C6 121.6(4) . . ?
C1 C3 C4 117.1(4) . . ?
C1 C3 F1 121.6(4) . . ?
C4 C3 F1 121.3(4) . . ?
C5 C4 C3 121.7(4) . . ?
C4 C5 C6 120.9(4) . . ?
C2 C6 C5 116.8(3) . . ?
C2 C6 C7 117.4(3) . . ?
C5 C6 C7 125.8(4) . . ?
C8 C7 C6 132.8(4) . . ?
C7 C8 C9 124.5(3) . . ?
C7 C8 C10 117.9(4) . . ?
C9 C8 C10 117.7(3) . . ?
N1 C9 C8 179.4(5) . . ?
O1 C10 O2 123.4(4) . . ?
O1 C10 C8 124.5(4) . . ?
O2 C10 C8 112.1(4) . . ?
C12 C11 O2 111.8(6) . . ?
C10 O2 C11 115.7(4) . . ?

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
C3 C1 C2 C6 1.0(7) . . . . ?
C2 C1 C3 C4 -1.0(7) . . . . ?
C2 C1 C3 F1 179.5(4) . . . . ?
C1 C3 C4 C5 0.5(7) . . . . ?
F1 C3 C4 C5 180.0(4) . . . . ?
C3 C4 C5 C6 0.1(8) . . . . ?
C1 C2 C6 C5 -0.4(7) . . . . ?
C1 C2 C6 C7 178.3(4) . . . . ?
C4 C5 C6 C2 -0.1(7) . . . . ?
C4 C5 C6 C7 -178.7(4) . . . . ?
C2 C6 C7 C8 -179.9(4) . . . . ?
C5 C6 C7 C8 -1.3(8) . . . . ?
C6 C7 C8 C9 -3.0(8) . . . . ?
C6 C7 C8 C10 178.3(4) . . . . ?
C7 C8 C9 N1 107(43) . . . . ?
C10 C8 C9 N1 -75(43) . . . . ?
C7 C8 C10 O1 -5.1(7) . . . . ?
C9 C8 C10 O1 176.1(5) . . . . ?
C7 C8 C10 O2 176.1(4) . . . . ?
C9 C8 C10 O2 -2.8(6) . . . . ?
O1 C10 O2 C11 -1.2(8) . . . . ?
C8 C10 O2 C11 177.7(5) . . . . ?
C12 C11 O2 C10 -172.5(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_10
_database_code_depnum_ccdc_archive 'CCDC 1510484'
_audit_update_record             
;
2016-10-18 deposited with the CCDC.
2017-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 Cl N O2'
_chemical_formula_weight         235.66

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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   14.903(7)
_cell_length_b                   5.3559(17)
_cell_length_c                   17.777(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 124.50(3)
_cell_angle_gamma                90.00
_cell_volume                     1169.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1004
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      20.30

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9463
_exptl_absorpt_correction_T_max  0.9637
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6434
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_sigmaI/netI    0.0940
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2044
_reflns_number_gt                1192
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0685P)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    refu
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2044
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1653
_refine_ls_wR_factor_gt          0.1368
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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 0.6333(3) 0.8306(5) 0.1705(2) 0.0600(8) Uani 1 1 d . . .
C2 C 0.5505(3) 0.6357(5) 0.1470(2) 0.0530(7) Uani 1 1 d . . .
C3 C 0.3641(3) 0.4772(5) 0.0213(2) 0.0547(7) Uani 1 1 d . . .
C4 C 0.1744(3) 0.1963(6) -0.0697(2) 0.0653(8) Uani 1 1 d . . .
C5 C 0.5762(2) 0.4610(5) 0.2181(2) 0.0570(8) Uani 1 1 d . . .
C6 C 0.3531(3) 0.2661(5) 0.0613(2) 0.0630(8) Uani 1 1 d . . .
H6 H 0.4104 0.2181 0.1196 0.076 Uiso 1 1 calc R . .
C7 C 0.2589(3) 0.1279(5) 0.0160(2) 0.0679(9) Uani 1 1 d . . .
H7 H 0.2526 -0.0122 0.0437 0.081 Uiso 1 1 calc R . .
C8 C 0.4591(3) 0.6356(5) 0.0636(2) 0.0545(8) Uani 1 1 d . . .
C9 C 0.8066(3) 0.9849(7) 0.2890(2) 0.0846(11) Uani 1 1 d . . .
H9A H 0.8515 0.9462 0.2670 0.102 Uiso 1 1 calc R . .
H9B H 0.7756 1.1497 0.2672 0.102 Uiso 1 1 calc R . .
C10 C 0.8722(4) 0.9808(9) 0.3879(3) 0.1251(17) Uani 1 1 d . . .
H10A H 0.8277 1.0236 0.4092 0.188 Uiso 1 1 calc R . .
H10B H 0.9305 1.0994 0.4109 0.188 Uiso 1 1 calc R . .
H10C H 0.9020 0.8167 0.4090 0.188 Uiso 1 1 calc R . .
C11 C 0.2759(3) 0.5395(6) -0.0665(2) 0.0658(9) Uani 1 1 d . . .
H11 H 0.2813 0.6778 -0.0953 0.079 Uiso 1 1 calc R . .
C12 C 0.1816(3) 0.4023(6) -0.1114(2) 0.0746(9) Uani 1 1 d . . .
H12 H 0.1233 0.4488 -0.1694 0.089 Uiso 1 1 calc R . .
Cl1 Cl 0.05649(8) 0.02105(18) -0.12569(8) 0.1020(5) Uani 1 1 d . . .
H1M H 0.454(2) 0.760(4) 0.0244(18) 0.057(7) Uiso 1 1 d . . .
N1 N 0.5979(2) 0.3245(5) 0.27530(18) 0.0745(8) Uani 1 1 d . . .
O1 O 0.62267(19) 0.9925(4) 0.11961(15) 0.0756(7) Uani 1 1 d . . .
O2 O 0.72060(18) 0.8018(4) 0.25547(15) 0.0720(6) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.197(3) . ?
C1 O2 1.331(4) . ?
C1 C2 1.485(4) . ?
C2 C8 1.330(4) . ?
C2 C5 1.439(4) . ?
C3 C6 1.394(4) . ?
C3 C11 1.397(4) . ?
C3 C8 1.443(4) . ?
C4 C12 1.366(4) . ?
C4 C7 1.367(4) . ?
C4 Cl1 1.725(3) . ?
C5 N1 1.140(3) . ?
C6 C7 1.374(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 H1M 0.93(3) . ?
C9 C10 1.449(5) . ?
C9 O2 1.447(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.372(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 124.6(3) . . ?
O1 C1 C2 124.3(3) . . ?
O2 C1 C2 111.1(3) . . ?
C8 C2 C5 125.1(3) . . ?
C8 C2 C1 118.5(3) . . ?
C5 C2 C1 116.4(3) . . ?
C6 C3 C11 117.1(3) . . ?
C6 C3 C8 125.1(3) . . ?
C11 C3 C8 117.8(3) . . ?
C12 C4 C7 121.0(3) . . ?
C12 C4 Cl1 119.6(3) . . ?
C7 C4 Cl1 119.4(3) . . ?
N1 C5 C2 179.0(4) . . ?
C7 C6 C3 121.0(3) . . ?
C7 C6 H6 119.5 . . ?
C3 C6 H6 119.5 . . ?
C4 C7 C6 120.0(3) . . ?
C4 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C2 C8 C3 131.6(3) . . ?
C2 C8 H1M 115.7(16) . . ?
C3 C8 H1M 112.7(16) . . ?
C10 C9 O2 108.7(3) . . ?
C10 C9 H9A 109.9 . . ?
O2 C9 H9A 109.9 . . ?
C10 C9 H9B 109.9 . . ?
O2 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C3 121.9(3) . . ?
C12 C11 H11 119.1 . . ?
C3 C11 H11 119.1 . . ?
C4 C12 C11 119.1(3) . . ?
C4 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C1 O2 C9 117.2(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C8 1.6(4) . . . . ?
O2 C1 C2 C8 -178.6(2) . . . . ?
O1 C1 C2 C5 -178.1(3) . . . . ?
O2 C1 C2 C5 1.8(3) . . . . ?
C8 C2 C5 N1 -174(100) . . . . ?
C1 C2 C5 N1 6(20) . . . . ?
C11 C3 C6 C7 -0.5(4) . . . . ?
C8 C3 C6 C7 179.4(2) . . . . ?
C12 C4 C7 C6 -0.4(5) . . . . ?
Cl1 C4 C7 C6 -179.9(2) . . . . ?
C3 C6 C7 C4 0.3(4) . . . . ?
C5 C2 C8 C3 0.9(5) . . . . ?
C1 C2 C8 C3 -178.7(2) . . . . ?
C6 C3 C8 C2 -5.5(5) . . . . ?
C11 C3 C8 C2 174.4(3) . . . . ?
C6 C3 C11 C12 1.0(4) . . . . ?
C8 C3 C11 C12 -178.9(2) . . . . ?
C7 C4 C12 C11 0.9(4) . . . . ?
Cl1 C4 C12 C11 -179.6(2) . . . . ?
C3 C11 C12 C4 -1.2(4) . . . . ?
O1 C1 O2 C9 2.1(4) . . . . ?
C2 C1 O2 C9 -177.7(2) . . . . ?
C10 C9 O2 C1 158.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.045
