# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_S66-2
_database_code_depnum_ccdc_archive 'CCDC 1839512'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            '2,2*-Bifuran-3,3*-dicarboxylic acid'
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H6 O6'
_chemical_formula_sum            'C10 H6 O6'
_chemical_formula_weight         222.15

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   13.226(4)
_cell_length_b                   6.747(2)
_cell_length_c                   10.358(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.474(4)
_cell_angle_gamma                90.00
_cell_volume                     921.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(1)
_cell_measurement_reflns_used    2657
_cell_measurement_theta_min      3.090
_cell_measurement_theta_max      27.727

_exptl_crystal_description       Prizem
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9400
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_process_details   'Bruker SADABS V2.05'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(1)
_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            4546
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0183
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         26.98
_reflns_number_total             986
_reflns_number_gt                938
_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)+(0.0580P)²+0.4816P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         986
_refine_ls_number_parameters     86
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1230
_refine_ls_wR_factor_gt          0.1216
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_restrained_S_all      1.181
_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 0.95410(12) 0.5577(2) 0.28406(14) 0.0373(4) Uani 1 1 d . . .
C2 C 0.90979(11) 0.4247(2) 0.36141(14) 0.0366(4) Uani 1 1 d . . .
C3 C 0.81676(13) 0.5118(3) 0.39368(16) 0.0448(4) Uani 1 1 d . . .
H3 H 0.7683(16) 0.450(3) 0.4473(19) 0.053(5) Uiso 1 1 d . . .
C4 C 0.81148(15) 0.6887(3) 0.33694(19) 0.0522(5) Uani 1 1 d . . .
H4 H 0.7647(18) 0.789(4) 0.336(2) 0.063(6) Uiso 1 1 d . . .
C5 C 0.94881(12) 0.2344(2) 0.41278(14) 0.0367(4) Uani 1 1 d . . .
O1 O 0.89492(10) 0.72259(18) 0.26864(12) 0.0503(4) Uani 1 1 d . . .
O2 O 1.04163(9) 0.1911(2) 0.39242(13) 0.0516(4) Uani 1 1 d . . .
H2O H 1.061(2) 0.068(5) 0.435(3) 0.095(9) Uiso 1 1 d . . .
O3 O 0.89468(9) 0.12817(19) 0.47476(13) 0.0542(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.362(2) . ?
C1 C2 1.365(2) . ?
C1 C1 1.451(3) 2_755 ?
C2 C3 1.427(2) . ?
C2 C5 1.468(2) . ?
C3 C4 1.330(3) . ?
C3 H3 0.97(2) . ?
C4 O1 1.376(2) . ?
C4 H4 0.92(2) . ?
C5 O3 1.2289(19) . ?
C5 O2 1.295(2) . ?
O2 H2O 0.97(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
O1 C1 C2 109.66(14) . . ?
O1 C1 C1 115.97(10) . 2_755 ?
C2 C1 C1 134.35(11) . 2_755 ?
C1 C2 C3 106.52(14) . . ?
C1 C2 C5 129.25(14) . . ?
C3 C2 C5 124.09(15) . . ?
C4 C3 C2 106.41(16) . . ?
C4 C3 H3 128.6(13) . . ?
C2 C3 H3 125.0(13) . . ?
C3 C4 O1 111.11(15) . . ?
C3 C4 H4 132.9(14) . . ?
O1 C4 H4 116.0(14) . . ?
O3 C5 O2 123.48(15) . . ?
O3 C5 C2 119.79(15) . . ?
O2 C5 C2 116.69(14) . . ?
C1 O1 C4 106.29(13) . . ?
C5 O2 H2O 109.8(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2O O3 0.97(3) 1.70(3) 2.6574(18) 172(3) 5_756

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        26.98
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.060
####################################################################### 
# 
# 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_S68-4a
_database_code_depnum_ccdc_archive 'CCDC 1839515'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-08-09 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 Br N O4'
_chemical_formula_sum            'C16 H16 Br N O4'
_chemical_formula_weight         366.21

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'
Br Br -0.2901 2.4595 '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
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   19.822(3)
_cell_length_b                   7.252(1)
_cell_length_c                   21.178(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3044.3(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    292(1)
_cell_measurement_reflns_used    6593
_cell_measurement_theta_min      2.815
_cell_measurement_theta_max      24.518

_exptl_crystal_description       Prizem
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.598
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1488
_exptl_absorpt_coefficient_mu    2.718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4674
_exptl_absorpt_correction_T_max  0.7189
_exptl_absorpt_process_details   'Bruker SADABS V2.05'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      292(1)
_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            32361
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         28.04
_reflns_number_total             3642
_reflns_number_gt                2579
_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)+(0.0547P)²+0.5154P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3642
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.1010
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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
Br1 Br 0.206391(14) 0.32265(4) 0.484773(12) 0.06047(12) Uani 1 1 d . . .
C1 C 0.10988(11) 0.1083(3) 0.71151(10) 0.0492(5) Uani 1 1 d . . .
C2 C 0.15723(11) 0.1560(3) 0.66111(10) 0.0447(5) Uani 1 1 d . . .
C3 C 0.22599(11) 0.1592(3) 0.65965(11) 0.0441(5) Uani 1 1 d . . .
C4 C 0.27142(11) 0.1162(3) 0.70885(11) 0.0447(5) Uani 1 1 d . . .
C5 C 0.25749(11) 0.0629(3) 0.76823(10) 0.0453(5) Uani 1 1 d . . .
C6 C 0.19346(11) 0.0352(3) 0.80132(10) 0.0490(5) Uani 1 1 d . . .
C7 C 0.19207(11) 0.2446(3) 0.56644(10) 0.0491(5) Uani 1 1 d . . .
C8 C 0.13588(12) 0.2120(3) 0.59954(11) 0.0513(5) Uani 1 1 d . . .
H8 H 0.0917 0.2235 0.5853 0.062 Uiso 1 1 calc R . .
C9 C 0.36859(12) 0.0773(3) 0.75533(12) 0.0608(6) Uani 1 1 d . . .
H9 H 0.4148 0.0726 0.7626 0.073 Uiso 1 1 calc R . .
C10 C 0.32133(12) 0.0366(3) 0.79821(12) 0.0559(6) Uani 1 1 d . . .
H10 H 0.3286 -0.0014 0.8396 0.067 Uiso 1 1 calc R . .
C11 C 0.07259(12) 0.0019(3) 0.81431(11) 0.0555(6) Uani 1 1 d . . .
H11A H 0.0867 -0.0942 0.8433 0.067 Uiso 1 1 calc R . .
H11B H 0.0354 -0.0458 0.7894 0.067 Uiso 1 1 calc R . .
C12 C 0.04833(13) 0.1674(3) 0.85197(12) 0.0579(6) Uani 1 1 d . . .
H12A H 0.0851 0.2149 0.8774 0.070 Uiso 1 1 calc R . .
H12B H 0.0341 0.2641 0.8233 0.070 Uiso 1 1 calc R . .
C13 C -0.01011(12) 0.1138(4) 0.89449(12) 0.0600(6) Uani 1 1 d . . .
H13A H 0.0012 0.0003 0.9163 0.072 Uiso 1 1 calc R . .
H13B H -0.0494 0.0897 0.8685 0.072 Uiso 1 1 calc R . .
C14 C -0.02795(12) 0.2606(4) 0.94328(13) 0.0623(6) Uani 1 1 d . . .
H14A H 0.0108 0.2819 0.9703 0.075 Uiso 1 1 calc R . .
H14B H -0.0382 0.3752 0.9217 0.075 Uiso 1 1 calc R . .
C15 C -0.08750(14) 0.2060(4) 0.98355(12) 0.0672(7) Uani 1 1 d . . .
H15A H -0.1274 0.2000 0.9571 0.081 Uiso 1 1 calc R . .
H15B H -0.0796 0.0836 1.0005 0.081 Uiso 1 1 calc R . .
C16 C -0.10084(15) 0.3362(4) 1.03736(15) 0.0756(8) Uani 1 1 d . . .
H16A H -0.0612 0.3457 1.0632 0.113 Uiso 1 1 calc R . .
H16B H -0.1377 0.2904 1.0623 0.113 Uiso 1 1 calc R . .
H16C H -0.1122 0.4557 1.0209 0.113 Uiso 1 1 calc R . .
N1 N 0.12974(9) 0.0481(2) 0.77149(8) 0.0473(4) Uani 1 1 d . . .
O1 O 0.04964(8) 0.1221(3) 0.70006(9) 0.0743(5) Uani 1 1 d . . .
O2 O 0.19525(8) -0.0032(3) 0.85697(8) 0.0700(5) Uani 1 1 d . . .
O3 O 0.24867(8) 0.2136(2) 0.60214(7) 0.0484(4) Uani 1 1 d . . .
O4 O 0.33908(8) 0.1271(2) 0.69881(8) 0.0551(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C7 1.842(2) . ?
C1 O1 1.222(3) . ?
C1 N1 1.400(3) . ?
C1 C2 1.463(3) . ?
C2 C3 1.363(3) . ?
C2 C8 1.430(3) . ?
C3 O3 1.357(3) . ?
C3 C4 1.412(3) . ?
C4 C5 1.344(3) . ?
C4 O4 1.360(3) . ?
C5 C10 1.429(3) . ?
C5 C6 1.464(3) . ?
C6 O2 1.211(3) . ?
C6 N1 1.415(3) . ?
C7 C8 1.337(3) . ?
C7 O3 1.371(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.337(3) . ?
C9 O4 1.380(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 N1 1.489(3) . ?
C11 C12 1.519(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.518(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.525(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.509(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.503(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 118.7(2) . . ?
O1 C1 C2 117.6(2) . . ?
N1 C1 C2 123.7(2) . . ?
C3 C2 C8 105.69(19) . . ?
C3 C2 C1 131.4(2) . . ?
C8 C2 C1 122.9(2) . . ?
O3 C3 C2 110.88(19) . . ?
O3 C3 C4 121.01(19) . . ?
C2 C3 C4 128.1(2) . . ?
C5 C4 O4 111.43(19) . . ?
C5 C4 C3 128.5(2) . . ?
O4 C4 C3 120.0(2) . . ?
C4 C5 C10 105.8(2) . . ?
C4 C5 C6 131.7(2) . . ?
C10 C5 C6 122.5(2) . . ?
O2 C6 N1 118.4(2) . . ?
O2 C6 C5 118.2(2) . . ?
N1 C6 C5 123.44(19) . . ?
C8 C7 O3 111.3(2) . . ?
C8 C7 Br1 132.45(18) . . ?
O3 C7 Br1 116.22(16) . . ?
C7 C8 C2 106.4(2) . . ?
C7 C8 H8 126.8 . . ?
C2 C8 H8 126.8 . . ?
C10 C9 O4 110.5(2) . . ?
C10 C9 H9 124.8 . . ?
O4 C9 H9 124.8 . . ?
C9 C10 C5 106.8(2) . . ?
C9 C10 H10 126.6 . . ?
C5 C10 H10 126.6 . . ?
N1 C11 C12 112.54(19) . . ?
N1 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
N1 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 110.5(2) . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 C14 113.6(2) . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C13 112.4(2) . . ?
C15 C14 H14A 109.1 . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C14 113.7(2) . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 N1 C6 132.58(18) . . ?
C1 N1 C11 114.13(18) . . ?
C6 N1 C11 113.09(18) . . ?
C3 O3 C7 105.74(17) . . ?
C4 O4 C9 105.49(18) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        28.04
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_C6-2BFI
_database_code_depnum_ccdc_archive 'CCDC 1839517'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H32 N2 O8, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C32.50 H33 Cl N2 O8'
_chemical_formula_weight         615.06

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'
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
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   16.043(5)
_cell_length_b                   9.527(3)
_cell_length_c                   39.119(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.887(5)
_cell_angle_gamma                90.00
_cell_volume                     5947(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    143(1)
_cell_measurement_reflns_used    4456
_cell_measurement_theta_min      2.201
_cell_measurement_theta_max      21.936

_exptl_crystal_description       Needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2584
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8926
_exptl_absorpt_correction_T_max  0.9782
_exptl_absorpt_process_details   'Bruker SADABS V2.05'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      143(1)
_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            53871
_diffrn_reflns_av_R_equivalents  0.1179
_diffrn_reflns_av_sigmaI/netI    0.0942
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         1.57
_diffrn_reflns_theta_max         25.00
_reflns_number_total             10463
_reflns_number_gt                7387
_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)+(0.0820P)²+6.5927P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         10463
_refine_ls_number_parameters     788
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1380
_refine_ls_R_factor_gt           0.0949
_refine_ls_wR_factor_ref         0.2145
_refine_ls_wR_factor_gt          0.1940
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3380(3) 0.4951(4) 0.61182(11) 0.0214(10) Uani 1 1 d . . .
C2 C 0.2889(2) 0.4089(4) 0.58621(11) 0.0189(9) Uani 1 1 d . . .
C3 C 0.2815(2) 0.2661(4) 0.58255(11) 0.0189(9) Uani 1 1 d . . .
C4 C 0.3189(3) 0.1621(4) 0.60460(12) 0.0230(10) Uani 1 1 d . . .
C5 C 0.3626(3) 0.1779(4) 0.63578(11) 0.0196(9) Uani 1 1 d . . .
C6 C 0.3873(3) 0.3038(4) 0.65622(12) 0.0251(10) Uani 1 1 d . . .
C7 C 0.2387(3) 0.4671(4) 0.55772(11) 0.0234(10) Uani 1 1 d . . .
H7 H 0.2310 0.5641 0.5528 0.028 Uiso 1 1 calc R . .
C8 C 0.2039(3) 0.3590(4) 0.53891(11) 0.0208(10) Uani 1 1 d . . .
C9 C 0.3518(3) -0.0483(5) 0.62351(12) 0.0297(11) Uani 1 1 d . . .
H9 H 0.3572 -0.1475 0.6248 0.036 Uiso 1 1 calc R . .
C10 C 0.3829(3) 0.0387(4) 0.64787(12) 0.0275(11) Uani 1 1 d . . .
H10 H 0.4129 0.0139 0.6692 0.033 Uiso 1 1 calc R . .
C11 C 0.4265(3) 0.5499(4) 0.66393(11) 0.0238(10) Uani 1 1 d . . .
H11A H 0.4483 0.6237 0.6494 0.029 Uiso 1 1 calc R . .
H11B H 0.4749 0.5064 0.6777 0.029 Uiso 1 1 calc R . .
C12 C 0.3692(3) 0.6166(5) 0.68788(12) 0.0274(11) Uani 1 1 d . . .
H12A H 0.3469 0.5434 0.7024 0.033 Uiso 1 1 calc R . .
H12B H 0.3212 0.6619 0.6742 0.033 Uiso 1 1 calc R . .
C13 C 0.4173(3) 0.7258(4) 0.71058(11) 0.0256(10) Uani 1 1 d . . .
H13A H 0.4601 0.6772 0.7263 0.031 Uiso 1 1 calc R . .
H13B H 0.4470 0.7891 0.6958 0.031 Uiso 1 1 calc R . .
C14 C 0.3627(3) 0.8133(5) 0.73166(12) 0.0284(11) Uani 1 1 d . . .
H14A H 0.3345 0.7505 0.7470 0.034 Uiso 1 1 calc R . .
H14B H 0.3188 0.8597 0.7160 0.034 Uiso 1 1 calc R . .
C15 C 0.4112(3) 0.9250(5) 0.75333(13) 0.0348(12) Uani 1 1 d . . .
H15A H 0.4558 0.8788 0.7687 0.042 Uiso 1 1 calc R . .
H15B H 0.4385 0.9890 0.7380 0.042 Uiso 1 1 calc R . .
C16 C 0.3570(3) 1.0094(6) 0.77463(14) 0.0491(15) Uani 1 1 d . . .
H16A H 0.3134 1.0573 0.7595 0.074 Uiso 1 1 calc R . .
H16B H 0.3914 1.0792 0.7880 0.074 Uiso 1 1 calc R . .
H16C H 0.3307 0.9470 0.7903 0.074 Uiso 1 1 calc R . .
C17 C 0.1437(3) 0.3489(4) 0.50957(11) 0.0230(10) Uani 1 1 d . . .
C18 C 0.1001(3) 0.2445(4) 0.49275(11) 0.0235(10) Uani 1 1 d . . .
H18 H 0.1056 0.1469 0.4974 0.028 Uiso 1 1 calc R . .
C19 C 0.0444(3) 0.3081(4) 0.46668(11) 0.0205(10) Uani 1 1 d . . .
C20 C 0.0596(3) 0.4498(5) 0.46909(11) 0.0222(10) Uani 1 1 d . . .
C21 C 0.0219(2) 0.5585(4) 0.44882(11) 0.0188(9) Uani 1 1 d . . .
C22 C -0.0357(3) 0.5488(4) 0.42090(11) 0.0237(10) Uani 1 1 d . . .
C23 C -0.0782(3) 0.4273(4) 0.40407(11) 0.0228(10) Uani 1 1 d . . .
C24 C -0.0166(3) 0.2282(5) 0.44351(12) 0.0270(11) Uani 1 1 d . . .
C25 C -0.0512(3) 0.6916(5) 0.40952(11) 0.0249(10) Uani 1 1 d . . .
H25 H -0.0884 0.7219 0.3905 0.030 Uiso 1 1 calc R . .
C26 C -0.0027(3) 0.7724(5) 0.43119(12) 0.0297(11) Uani 1 1 d . . .
H26 H -0.0009 0.8719 0.4298 0.036 Uiso 1 1 calc R . .
C27 C -0.1289(3) 0.1869(5) 0.39872(12) 0.0263(11) Uani 1 1 d . . .
H27A H -0.1799 0.2360 0.3885 0.032 Uiso 1 1 calc R . .
H27B H -0.1463 0.1147 0.4148 0.032 Uiso 1 1 calc R . .
C28 C -0.0859(3) 0.1168(5) 0.37059(12) 0.0306(11) Uani 1 1 d . . .
H28A H -0.0365 0.0645 0.3811 0.037 Uiso 1 1 calc R . .
H28B H -0.0657 0.1900 0.3555 0.037 Uiso 1 1 calc R . .
C29 C -0.1426(3) 0.0163(5) 0.34886(12) 0.0316(11) Uani 1 1 d . . .
H29A H -0.1908 0.0690 0.3374 0.038 Uiso 1 1 calc R . .
H29B H -0.1648 -0.0550 0.3640 0.038 Uiso 1 1 calc R . .
C30 C -0.0965(3) -0.0573(6) 0.32178(13) 0.0418(13) Uani 1 1 d . . .
H30A H -0.0697 0.0147 0.3083 0.050 Uiso 1 1 calc R . .
H30B H -0.0514 -0.1158 0.3336 0.050 Uiso 1 1 calc R . .
C31 C -0.1517(4) -0.1498(6) 0.29710(14) 0.0514(15) Uani 1 1 d . . .
H31A H -0.2002 -0.0941 0.2870 0.062 Uiso 1 1 calc R . .
H31B H -0.1194 -0.1796 0.2781 0.062 Uiso 1 1 calc R . .
C32 C -0.1837(4) -0.2793(7) 0.31422(17) 0.0665(19) Uani 1 1 d . . .
H32A H -0.1360 -0.3365 0.3237 0.100 Uiso 1 1 calc R . .
H32B H -0.2191 -0.3342 0.2972 0.100 Uiso 1 1 calc R . .
H32C H -0.2165 -0.2506 0.3328 0.100 Uiso 1 1 calc R . .
N1 N 0.3822(2) 0.4403(3) 0.64130(9) 0.0210(8) Uani 1 1 d . . .
N2 N -0.0714(2) 0.2899(4) 0.41803(9) 0.0230(8) Uani 1 1 d . . .
O1 O 0.33949(19) 0.6223(3) 0.60649(8) 0.0264(7) Uani 1 1 d . . .
O2 O 0.4164(2) 0.2909(3) 0.68552(9) 0.0357(8) Uani 1 1 d . . .
O3 O 0.23018(17) 0.2324(3) 0.55398(7) 0.0212(7) Uani 1 1 d . . .
O4 O 0.31031(18) 0.0228(3) 0.59591(8) 0.0250(7) Uani 1 1 d . . .
O5 O -0.1239(2) 0.4474(3) 0.37786(8) 0.0335(8) Uani 1 1 d . . .
O6 O -0.0177(2) 0.1019(3) 0.44767(9) 0.0384(9) Uani 1 1 d . . .
O7 O 0.11935(17) 0.4778(3) 0.49535(7) 0.0219(7) Uani 1 1 d . . .
O8 O 0.04394(18) 0.6951(3) 0.45553(7) 0.0251(7) Uani 1 1 d . . .
C33 C 0.1810(2) -0.0074(4) 0.90108(11) 0.0192(9) Uani 1 1 d . . .
C34 C 0.2346(3) 0.0638(4) 0.92863(11) 0.0189(9) Uani 1 1 d . . .
C35 C 0.2480(3) 0.2031(4) 0.93546(11) 0.0207(10) Uani 1 1 d . . .
C36 C 0.2105(3) 0.3196(4) 0.91716(12) 0.0235(10) Uani 1 1 d . . .
C37 C 0.1596(3) 0.3208(4) 0.88756(12) 0.0236(10) Uani 1 1 d . . .
C38 C 0.1248(3) 0.2066(4) 0.86551(12) 0.0261(11) Uani 1 1 d . . .
C39 C 0.2856(2) -0.0088(4) 0.95463(11) 0.0196(9) Uani 1 1 d . . .
H39 H 0.2901 -0.1078 0.9572 0.023 Uiso 1 1 calc R . .
C40 C 0.3266(2) 0.0880(4) 0.97508(11) 0.0197(10) Uani 1 1 d . . .
C41 C 0.1416(3) 0.4669(5) 0.88040(13) 0.0306(11) Uani 1 1 d . . .
H41 H 0.1077 0.5046 0.8613 0.037 Uiso 1 1 calc R . .
C42 C 0.1828(3) 0.5380(5) 0.90631(14) 0.0365(13) Uani 1 1 d . . .
H42 H 0.1820 0.6373 0.9083 0.044 Uiso 1 1 calc R . .
C43 C 0.0844(3) -0.0312(5) 0.84959(12) 0.0281(11) Uani 1 1 d . . .
H43A H 0.0321 0.0168 0.8404 0.034 Uiso 1 1 calc R . .
H43B H 0.0686 -0.1173 0.8615 0.034 Uiso 1 1 calc R . .
C44 C 0.1326(3) -0.0718(5) 0.82016(11) 0.0274(11) Uani 1 1 d . . .
H44A H 0.1858 -0.1175 0.8292 0.033 Uiso 1 1 calc R . .
H44B H 0.1467 0.0137 0.8076 0.033 Uiso 1 1 calc R . .
C45 C 0.0832(3) -0.1708(6) 0.79565(13) 0.0425(13) Uani 1 1 d . . .
H45A H 0.0697 -0.2559 0.8085 0.051 Uiso 1 1 calc R . .
H45B H 0.0296 -0.1250 0.7873 0.051 Uiso 1 1 calc R . .
C46 C 0.1259(3) -0.2146(6) 0.76543(13) 0.0419(13) Uani 1 1 d . . .
H46A H 0.1790 -0.2621 0.7738 0.050 Uiso 1 1 calc R . .
H46B H 0.1405 -0.1293 0.7529 0.050 Uiso 1 1 calc R . .
C47 C 0.0757(4) -0.3122(8) 0.74023(16) 0.0662(19) Uani 1 1 d . . .
H47A H 0.0592 -0.3965 0.7527 0.079 Uiso 1 1 calc R . .
H47B H 0.0239 -0.2638 0.7307 0.079 Uiso 1 1 calc R . .
C48 C 0.1236(4) -0.3565(8) 0.71161(16) 0.071(2) Uani 1 1 d . . .
H48A H 0.1454 -0.2734 0.7007 0.106 Uiso 1 1 calc R . .
H48B H 0.0866 -0.4086 0.6946 0.106 Uiso 1 1 calc R . .
H48C H 0.1703 -0.4167 0.7206 0.106 Uiso 1 1 calc R . .
C49 C 0.3857(2) 0.0892(4) 1.00494(11) 0.0208(10) Uani 1 1 d . . .
C50 C 0.4240(3) 0.1930(4) 1.02369(11) 0.0223(10) Uani 1 1 d . . .
H50 H 0.4174 0.2908 1.0195 0.027 Uiso 1 1 calc R . .
C51 C 0.4764(3) 0.1296(4) 1.05111(11) 0.0198(10) Uani 1 1 d . . .
C52 C 0.4649(3) -0.0122(4) 1.04684(11) 0.0203(10) Uani 1 1 d . . .
C53 C 0.5027(3) -0.1195(4) 1.06763(11) 0.0216(10) Uani 1 1 d . . .
C54 C 0.5595(2) -0.1089(4) 1.09553(11) 0.0195(9) Uani 1 1 d . . .
C55 C 0.6024(3) 0.0132(4) 1.11287(12) 0.0223(10) Uani 1 1 d . . .
C56 C 0.5265(3) 0.2103(4) 1.07721(11) 0.0235(10) Uani 1 1 d . . .
C57 C 0.5778(3) -0.2500(4) 1.10708(12) 0.0273(11) Uani 1 1 d . . .
H57 H 0.6152 -0.2780 1.1263 0.033 Uiso 1 1 calc R . .
C58 C 0.5317(3) -0.3329(5) 1.08541(12) 0.0323(12) Uani 1 1 d . . .
H58 H 0.5317 -0.4325 1.0869 0.039 Uiso 1 1 calc R . .
C59 C 0.6406(3) 0.2581(4) 1.12103(12) 0.0264(11) Uani 1 1 d . . .
H59A H 0.6527 0.3349 1.1052 0.032 Uiso 1 1 calc R . .
H59B H 0.6945 0.2130 1.1293 0.032 Uiso 1 1 calc R . .
C60 C 0.6028(3) 0.3201(5) 1.15136(12) 0.0300(11) Uani 1 1 d . . .
H60A H 0.5861 0.2435 1.1663 0.036 Uiso 1 1 calc R . .
H60B H 0.5518 0.3739 1.1431 0.036 Uiso 1 1 calc R . .
C61 C 0.6644(3) 0.4163(5) 1.17195(12) 0.0322(12) Uani 1 1 d . . .
H61A H 0.7096 0.3584 1.1839 0.039 Uiso 1 1 calc R . .
H61B H 0.6902 0.4792 1.1559 0.039 Uiso 1 1 calc R . .
C62 C 0.6259(3) 0.5051(5) 1.19827(12) 0.0354(12) Uani 1 1 d . . .
H62A H 0.5915 0.4438 1.2117 0.042 Uiso 1 1 calc R . .
H62B H 0.5879 0.5747 1.1860 0.042 Uiso 1 1 calc R . .
C63 C 0.6893(3) 0.5828(6) 1.22314(14) 0.0448(14) Uani 1 1 d . . .
H63A H 0.6586 0.6429 1.2383 0.054 Uiso 1 1 calc R . .
H63B H 0.7217 0.5133 1.2379 0.054 Uiso 1 1 calc R . .
C64 C 0.7496(4) 0.6733(6) 1.20565(15) 0.0556(16) Uani 1 1 d . . .
H64A H 0.7819 0.6143 1.1912 0.083 Uiso 1 1 calc R . .
H64B H 0.7880 0.7207 1.2231 0.083 Uiso 1 1 calc R . .
H64C H 0.7182 0.7436 1.1913 0.083 Uiso 1 1 calc R . .
N3 N 0.1322(2) 0.0624(4) 0.87474(9) 0.0223(8) Uani 1 1 d . . .
N4 N 0.5861(2) 0.1527(3) 1.10155(9) 0.0199(8) Uani 1 1 d . . .
O9 O 0.17882(19) -0.1356(3) 0.90194(8) 0.0272(7) Uani 1 1 d . . .
O10 O 0.0854(2) 0.2363(3) 0.83825(9) 0.0387(9) Uani 1 1 d . . .
O11 O 0.30368(17) 0.2211(3) 0.96346(7) 0.0224(7) Uani 1 1 d . . .
O12 O 0.22634(19) 0.4510(3) 0.92963(8) 0.0321(8) Uani 1 1 d . . .
O13 O 0.40994(17) -0.0400(3) 1.01897(7) 0.0227(7) Uani 1 1 d . . .
O14 O 0.48397(18) -0.2573(3) 1.06058(8) 0.0270(7) Uani 1 1 d . . .
O15 O 0.5166(2) 0.3390(3) 1.07664(8) 0.0323(8) Uani 1 1 d . . .
O16 O 0.6538(2) -0.0079(3) 1.13700(8) 0.0325(8) Uani 1 1 d . . .
C1C C 0.3060(4) 0.9077(9) 0.51653(19) 0.079(2) Uani 1 1 d . . .
H1C1 H 0.2961 1.0074 0.5220 0.095 Uiso 1 1 calc R . .
H1C2 H 0.3320 0.8621 0.5377 0.095 Uiso 1 1 calc R . .
Cl1 Cl 0.37575(9) 0.89965(15) 0.48536(4) 0.0498(4) Uani 1 1 d . . .
Cl2 Cl 0.20938(10) 0.82704(16) 0.50418(4) 0.0586(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.231(5) . ?
C1 N1 1.392(5) . ?
C1 C2 1.462(6) . ?
C2 C3 1.372(6) . ?
C2 C7 1.419(6) . ?
C3 O3 1.357(5) . ?
C3 C4 1.407(6) . ?
C4 C5 1.351(6) . ?
C4 O4 1.374(5) . ?
C5 C10 1.434(6) . ?
C5 C6 1.473(6) . ?
C6 O2 1.199(5) . ?
C6 N1 1.424(5) . ?
C7 C8 1.353(6) . ?
C7 H7 0.9500 . ?
C8 O3 1.389(5) . ?
C8 C17 1.425(6) . ?
C9 C10 1.322(6) . ?
C9 O4 1.385(5) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 N1 1.500(5) . ?
C11 C12 1.519(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.525(6) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.513(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.523(6) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.499(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.347(6) . ?
C17 O7 1.388(5) . ?
C18 C19 1.421(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.373(6) . ?
C19 C24 1.475(6) . ?
C20 O7 1.358(5) . ?
C20 C21 1.404(6) . ?
C21 C22 1.359(6) . ?
C21 O8 1.367(5) . ?
C22 C25 1.445(6) . ?
C22 C23 1.465(6) . ?
C23 O5 1.213(5) . ?
C23 N2 1.419(6) . ?
C24 O6 1.214(5) . ?
C24 N2 1.391(6) . ?
C25 C26 1.335(6) . ?
C25 H25 0.9500 . ?
C26 O8 1.364(5) . ?
C26 H26 0.9500 . ?
C27 N2 1.497(5) . ?
C27 C28 1.513(6) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.519(6) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.524(6) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.523(7) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.517(8) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 O9 1.222(5) . ?
C33 N3 1.397(5) . ?
C33 C34 1.474(6) . ?
C34 C35 1.367(6) . ?
C34 C39 1.418(6) . ?
C35 O11 1.351(5) . ?
C35 C36 1.420(6) . ?
C36 C37 1.347(6) . ?
C36 O12 1.358(5) . ?
C37 C41 1.443(6) . ?
C37 C38 1.463(6) . ?
C38 O10 1.215(5) . ?
C38 N3 1.422(5) . ?
C39 C40 1.347(6) . ?
C39 H39 0.9500 . ?
C40 O11 1.383(5) . ?
C40 C49 1.427(6) . ?
C41 C42 1.336(7) . ?
C41 H41 0.9500 . ?
C42 O12 1.370(5) . ?
C42 H42 0.9500 . ?
C43 N3 1.482(5) . ?
C43 C44 1.503(6) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 C45 1.510(6) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C46 1.486(7) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 C47 1.524(7) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 C48 1.482(8) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 C50 1.342(6) . ?
C49 O13 1.387(5) . ?
C50 C51 1.428(6) . ?
C50 H50 0.9500 . ?
C51 C52 1.371(6) . ?
C51 C56 1.454(6) . ?
C52 O13 1.356(5) . ?
C52 C53 1.404(6) . ?
C53 C54 1.352(6) . ?
C53 O14 1.369(5) . ?
C54 C57 1.439(6) . ?
C54 C55 1.481(6) . ?
C55 O16 1.205(5) . ?
C55 N4 1.416(5) . ?
C56 O15 1.236(5) . ?
C56 N4 1.391(5) . ?
C57 C58 1.327(6) . ?
C57 H57 0.9500 . ?
C58 O14 1.377(5) . ?
C58 H58 0.9500 . ?
C59 N4 1.489(5) . ?
C59 C60 1.507(6) . ?
C59 H59A 0.9900 . ?
C59 H59B 0.9900 . ?
C60 C61 1.517(6) . ?
C60 H60A 0.9900 . ?
C60 H60B 0.9900 . ?
C61 C62 1.512(6) . ?
C61 H61A 0.9900 . ?
C61 H61B 0.9900 . ?
C62 C63 1.525(7) . ?
C62 H62A 0.9900 . ?
C62 H62B 0.9900 . ?
C63 C64 1.512(8) . ?
C63 H63A 0.9900 . ?
C63 H63B 0.9900 . ?
C64 H64A 0.9800 . ?
C64 H64B 0.9800 . ?
C64 H64C 0.9800 . ?
C1C Cl1 1.739(7) . ?
C1C Cl2 1.753(7) . ?
C1C H1C1 0.9900 . ?
C1C H1C2 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 119.5(4) . . ?
O1 C1 C2 117.1(4) . . ?
N1 C1 C2 123.4(4) . . ?
C3 C2 C7 105.6(4) . . ?
C3 C2 C1 131.6(4) . . ?
C7 C2 C1 122.8(4) . . ?
O3 C3 C2 111.1(4) . . ?
O3 C3 C4 121.5(4) . . ?
C2 C3 C4 127.4(4) . . ?
C5 C4 O4 111.1(4) . . ?
C5 C4 C3 128.7(4) . . ?
O4 C4 C3 120.2(4) . . ?
C4 C5 C10 105.9(4) . . ?
C4 C5 C6 131.7(4) . . ?
C10 C5 C6 122.3(4) . . ?
O2 C6 N1 119.1(4) . . ?
O2 C6 C5 119.5(4) . . ?
N1 C6 C5 121.3(4) . . ?
C8 C7 C2 107.4(4) . . ?
C8 C7 H7 126.3 . . ?
C2 C7 H7 126.3 . . ?
C7 C8 O3 109.8(4) . . ?
C7 C8 C17 134.2(4) . . ?
O3 C8 C17 115.8(3) . . ?
C10 C9 O4 111.8(4) . . ?
C10 C9 H9 124.1 . . ?
O4 C9 H9 124.1 . . ?
C9 C10 C5 106.6(4) . . ?
C9 C10 H10 126.7 . . ?
C5 C10 H10 126.7 . . ?
N1 C11 C12 112.0(3) . . ?
N1 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
N1 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C13 110.0(4) . . ?
C11 C12 H12A 109.7 . . ?
C13 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
C13 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C14 C13 C12 114.0(4) . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 C15 113.4(4) . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C16 C15 C14 113.1(4) . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C14 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 O7 110.3(4) . . ?
C18 C17 C8 135.8(4) . . ?
O7 C17 C8 113.8(4) . . ?
C17 C18 C19 107.0(4) . . ?
C17 C18 H18 126.5 . . ?
C19 C18 H18 126.5 . . ?
C20 C19 C18 106.0(4) . . ?
C20 C19 C24 130.7(4) . . ?
C18 C19 C24 123.3(4) . . ?
O7 C20 C19 110.6(4) . . ?
O7 C20 C21 120.8(4) . . ?
C19 C20 C21 128.6(4) . . ?
C22 C21 O8 111.1(4) . . ?
C22 C21 C20 128.5(4) . . ?
O8 C21 C20 120.4(4) . . ?
C21 C22 C25 105.3(4) . . ?
C21 C22 C23 131.4(4) . . ?
C25 C22 C23 123.2(4) . . ?
O5 C23 N2 119.2(4) . . ?
O5 C23 C22 117.9(4) . . ?
N2 C23 C22 122.9(4) . . ?
O6 C24 N2 119.8(4) . . ?
O6 C24 C19 116.6(4) . . ?
N2 C24 C19 123.6(4) . . ?
C26 C25 C22 106.0(4) . . ?
C26 C25 H25 127.0 . . ?
C22 C25 H25 127.0 . . ?
C25 C26 O8 112.0(4) . . ?
C25 C26 H26 124.0 . . ?
O8 C26 H26 124.0 . . ?
N2 C27 C28 110.7(3) . . ?
N2 C27 H27A 109.5 . . ?
C28 C27 H27A 109.5 . . ?
N2 C27 H27B 109.5 . . ?
C28 C27 H27B 109.5 . . ?
H27A C27 H27B 108.1 . . ?
C27 C28 C29 113.2(4) . . ?
C27 C28 H28A 108.9 . . ?
C29 C28 H28A 108.9 . . ?
C27 C28 H28B 108.9 . . ?
C29 C28 H28B 108.9 . . ?
H28A C28 H28B 107.8 . . ?
C28 C29 C30 111.9(4) . . ?
C28 C29 H29A 109.2 . . ?
C30 C29 H29A 109.2 . . ?
C28 C29 H29B 109.2 . . ?
C30 C29 H29B 109.2 . . ?
H29A C29 H29B 107.9 . . ?
C31 C30 C29 114.5(4) . . ?
C31 C30 H30A 108.6 . . ?
C29 C30 H30A 108.6 . . ?
C31 C30 H30B 108.6 . . ?
C29 C30 H30B 108.6 . . ?
H30A C30 H30B 107.6 . . ?
C32 C31 C30 113.0(5) . . ?
C32 C31 H31A 109.0 . . ?
C30 C31 H31A 109.0 . . ?
C32 C31 H31B 109.0 . . ?
C30 C31 H31B 109.0 . . ?
H31A C31 H31B 107.8 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C1 N1 C6 133.2(4) . . ?
C1 N1 C11 113.5(3) . . ?
C6 N1 C11 112.9(3) . . ?
C24 N2 C23 133.2(4) . . ?
C24 N2 C27 113.4(3) . . ?
C23 N2 C27 113.1(3) . . ?
C3 O3 C8 106.0(3) . . ?
C4 O4 C9 104.5(3) . . ?
C20 O7 C17 106.1(3) . . ?
C26 O8 C21 105.5(3) . . ?
O9 C33 N3 118.8(4) . . ?
O9 C33 C34 117.1(4) . . ?
N3 C33 C34 124.1(4) . . ?
C35 C34 C39 105.4(4) . . ?
C35 C34 C33 131.2(4) . . ?
C39 C34 C33 123.4(4) . . ?
O11 C35 C34 111.0(4) . . ?
O11 C35 C36 121.4(4) . . ?
C34 C35 C36 127.6(4) . . ?
C37 C36 O12 112.1(4) . . ?
C37 C36 C35 128.9(4) . . ?
O12 C36 C35 119.0(4) . . ?
C36 C37 C41 105.4(4) . . ?
C36 C37 C38 131.4(4) . . ?
C41 C37 C38 123.1(4) . . ?
O10 C38 N3 118.0(4) . . ?
O10 C38 C37 118.5(4) . . ?
N3 C38 C37 123.5(4) . . ?
C40 C39 C34 107.6(4) . . ?
C40 C39 H39 126.2 . . ?
C34 C39 H39 126.2 . . ?
C39 C40 O11 109.6(4) . . ?
C39 C40 C49 137.2(4) . . ?
O11 C40 C49 113.2(4) . . ?
C42 C41 C37 105.6(4) . . ?
C42 C41 H41 127.2 . . ?
C37 C41 H41 127.2 . . ?
C41 C42 O12 112.1(4) . . ?
C41 C42 H42 123.9 . . ?
O12 C42 H42 123.9 . . ?
N3 C43 C44 113.0(3) . . ?
N3 C43 H43A 109.0 . . ?
C44 C43 H43A 109.0 . . ?
N3 C43 H43B 109.0 . . ?
C44 C43 H43B 109.0 . . ?
H43A C43 H43B 107.8 . . ?
C43 C44 C45 111.6(4) . . ?
C43 C44 H44A 109.3 . . ?
C45 C44 H44A 109.3 . . ?
C43 C44 H44B 109.3 . . ?
C45 C44 H44B 109.3 . . ?
H44A C44 H44B 108.0 . . ?
C46 C45 C44 115.2(4) . . ?
C46 C45 H45A 108.5 . . ?
C44 C45 H45A 108.5 . . ?
C46 C45 H45B 108.5 . . ?
C44 C45 H45B 108.5 . . ?
H45A C45 H45B 107.5 . . ?
C45 C46 C47 115.5(5) . . ?
C45 C46 H46A 108.4 . . ?
C47 C46 H46A 108.4 . . ?
C45 C46 H46B 108.4 . . ?
C47 C46 H46B 108.4 . . ?
H46A C46 H46B 107.5 . . ?
C48 C47 C46 112.5(5) . . ?
C48 C47 H47A 109.1 . . ?
C46 C47 H47A 109.1 . . ?
C48 C47 H47B 109.1 . . ?
C46 C47 H47B 109.1 . . ?
H47A C47 H47B 107.8 . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C50 C49 O13 110.1(4) . . ?
C50 C49 C40 133.0(4) . . ?
O13 C49 C40 116.9(4) . . ?
C49 C50 C51 107.5(4) . . ?
C49 C50 H50 126.3 . . ?
C51 C50 H50 126.3 . . ?
C52 C51 C50 105.3(4) . . ?
C52 C51 C56 131.7(4) . . ?
C50 C51 C56 123.0(4) . . ?
O13 C52 C51 111.0(4) . . ?
O13 C52 C53 122.0(4) . . ?
C51 C52 C53 127.0(4) . . ?
C54 C53 O14 110.5(4) . . ?
C54 C53 C52 128.9(4) . . ?
O14 C53 C52 120.6(4) . . ?
C53 C54 C57 106.4(4) . . ?
C53 C54 C55 132.2(4) . . ?
C57 C54 C55 121.3(4) . . ?
O16 C55 N4 119.4(4) . . ?
O16 C55 C54 118.5(4) . . ?
N4 C55 C54 122.1(4) . . ?
O15 C56 N4 118.9(4) . . ?
O15 C56 C51 116.8(4) . . ?
N4 C56 C51 124.3(4) . . ?
C58 C57 C54 105.9(4) . . ?
C58 C57 H57 127.1 . . ?
C54 C57 H57 127.1 . . ?
C57 C58 O14 111.9(4) . . ?
C57 C58 H58 124.1 . . ?
O14 C58 H58 124.1 . . ?
N4 C59 C60 113.9(3) . . ?
N4 C59 H59A 108.8 . . ?
C60 C59 H59A 108.8 . . ?
N4 C59 H59B 108.8 . . ?
C60 C59 H59B 108.8 . . ?
H59A C59 H59B 107.7 . . ?
C59 C60 C61 111.2(4) . . ?
C59 C60 H60A 109.4 . . ?
C61 C60 H60A 109.4 . . ?
C59 C60 H60B 109.4 . . ?
C61 C60 H60B 109.4 . . ?
H60A C60 H60B 108.0 . . ?
C62 C61 C60 114.2(4) . . ?
C62 C61 H61A 108.7 . . ?
C60 C61 H61A 108.7 . . ?
C62 C61 H61B 108.7 . . ?
C60 C61 H61B 108.7 . . ?
H61A C61 H61B 107.6 . . ?
C61 C62 C63 114.5(4) . . ?
C61 C62 H62A 108.6 . . ?
C63 C62 H62A 108.6 . . ?
C61 C62 H62B 108.6 . . ?
C63 C62 H62B 108.6 . . ?
H62A C62 H62B 107.6 . . ?
C64 C63 C62 113.8(4) . . ?
C64 C63 H63A 108.8 . . ?
C62 C63 H63A 108.8 . . ?
C64 C63 H63B 108.8 . . ?
C62 C63 H63B 108.8 . . ?
H63A C63 H63B 107.7 . . ?
C63 C64 H64A 109.5 . . ?
C63 C64 H64B 109.5 . . ?
H64A C64 H64B 109.5 . . ?
C63 C64 H64C 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?
C33 N3 C38 132.3(4) . . ?
C33 N3 C43 114.6(3) . . ?
C38 N3 C43 112.8(4) . . ?
C56 N4 C55 132.6(4) . . ?
C56 N4 C59 114.2(3) . . ?
C55 N4 C59 113.1(3) . . ?
C35 O11 C40 106.4(3) . . ?
C36 O12 C42 104.8(4) . . ?
C52 O13 C49 106.1(3) . . ?
C53 O14 C58 105.4(3) . . ?
Cl1 C1C Cl2 113.7(4) . . ?
Cl1 C1C H1C1 108.8 . . ?
Cl2 C1C H1C1 108.8 . . ?
Cl1 C1C H1C2 108.8 . . ?
Cl2 C1C H1C2 108.8 . . ?
H1C1 C1C H1C2 107.7 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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_S66-3
_database_code_depnum_ccdc_archive 'CCDC 1839513'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            '2,2*-Bifuran-3,3*dicarboxylic anhydride '
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H4 O5'
_chemical_formula_sum            'C10 H4 O5'
_chemical_formula_weight         204.13

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc '

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                   9.814(2)
_cell_length_b                   18.944(4)
_cell_length_c                   8.825(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.819(4)
_cell_angle_gamma                90.00
_cell_volume                     1638.7(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(1)
_cell_measurement_reflns_used    4736
_cell_measurement_theta_min      2.549
_cell_measurement_theta_max      27.262

_exptl_crystal_description       Rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9474
_exptl_absorpt_correction_T_max  0.9865
_exptl_absorpt_process_details   'Bruker SADABS V2.05'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(1)
_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            14786
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2878
_reflns_number_gt                2760
_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)+(0.0353P)²+3.1015P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    Constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2878
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0758
_refine_ls_wR_factor_ref         0.1504
_refine_ls_wR_factor_gt          0.1485
_refine_ls_goodness_of_fit_ref   1.306
_refine_ls_restrained_S_all      1.306
_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 0.4340(3) 0.19088(17) 0.4130(3) 0.0165(7) Uani 1 1 d . . .
C2 C 0.4438(3) 0.12001(17) 0.3830(4) 0.0172(7) Uani 1 1 d . . .
C3 C 0.3491(3) 0.08667(18) 0.4782(4) 0.0224(8) Uani 1 1 d . . .
H3 H 0.3306 0.0375 0.4840 0.027 Uiso 1 1 calc R . .
C4 C 0.2917(3) 0.13764(19) 0.5571(4) 0.0239(8) Uani 1 1 d . . .
H4 H 0.2251 0.1301 0.6299 0.029 Uiso 1 1 calc R . .
C5 C 0.5049(3) 0.24769(16) 0.3465(4) 0.0157(7) Uani 1 1 d . . .
C6 C 0.6052(3) 0.24630(17) 0.2450(4) 0.0175(7) Uani 1 1 d . . .
C7 C 0.6410(3) 0.31832(17) 0.2180(4) 0.0194(7) Uani 1 1 d . . .
H7 H 0.7085 0.3351 0.1534 0.023 Uiso 1 1 calc R . .
C8 C 0.5594(3) 0.35721(18) 0.3027(4) 0.0228(8) Uani 1 1 d . . .
H8 H 0.5598 0.4073 0.3061 0.027 Uiso 1 1 calc R . .
C9 C 0.5262(3) 0.08323(17) 0.2757(4) 0.0186(7) Uani 1 1 d . . .
C10 C 0.6683(3) 0.18650(16) 0.1715(3) 0.0161(7) Uani 1 1 d . . .
C11 C 0.0758(3) 0.13162(16) 0.2511(4) 0.0178(7) Uani 1 1 d . . .
C12 C -0.0255(3) 0.12873(17) 0.3516(4) 0.0173(7) Uani 1 1 d . . .
C13 C -0.0403(3) 0.19905(18) 0.4082(4) 0.0229(8) Uani 1 1 d . . .
H13 H -0.1023 0.2147 0.4804 0.027 Uiso 1 1 calc R . .
C14 C 0.0512(4) 0.23812(17) 0.3381(4) 0.0254(8) Uani 1 1 d . . .
H14 H 0.0641 0.2873 0.3538 0.031 Uiso 1 1 calc R . .
C15 C 0.1332(3) 0.07624(17) 0.1645(4) 0.0186(7) Uani 1 1 d . . .
C16 C 0.1002(3) 0.00596(17) 0.1621(4) 0.0180(7) Uani 1 1 d . . .
C17 C 0.1875(3) -0.02564(18) 0.0562(4) 0.0213(7) Uani 1 1 d . . .
H17 H 0.1899 -0.0740 0.0282 0.026 Uiso 1 1 calc R . .
C18 C 0.2651(4) 0.02616(19) 0.0044(4) 0.0244(8) Uani 1 1 d . . .
H18 H 0.3327 0.0199 -0.0679 0.029 Uiso 1 1 calc R . .
C19 C -0.1069(3) 0.06931(18) 0.3979(4) 0.0196(7) Uani 1 1 d . . .
C20 C -0.0034(3) -0.03180(18) 0.2416(4) 0.0205(7) Uani 1 1 d . . .
O1 O 0.3423(2) 0.20298(12) 0.5187(3) 0.0208(5) Uani 1 1 d . . .
O2 O 0.4750(2) 0.31484(11) 0.3843(3) 0.0203(5) Uani 1 1 d . . .
O3 O 0.6229(2) 0.11749(11) 0.1919(3) 0.0212(5) Uani 1 1 d . . .
O4 O 0.5175(3) 0.02119(12) 0.2523(3) 0.0272(6) Uani 1 1 d . . .
O5 O 0.7609(2) 0.19193(12) 0.0880(3) 0.0232(6) Uani 1 1 d . . .
O6 O 0.1244(2) 0.19802(12) 0.2405(3) 0.0248(6) Uani 1 1 d . . .
O7 O 0.2341(2) 0.09008(12) 0.0700(3) 0.0231(6) Uani 1 1 d . . .
O8 O -0.0862(2) 0.00109(12) 0.3447(3) 0.0223(5) Uani 1 1 d . . .
O9 O -0.1974(2) 0.07423(13) 0.4849(3) 0.0285(6) Uani 1 1 d . . .
O10 O -0.0249(3) -0.09388(12) 0.2244(3) 0.0285(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 1.347(4) . ?
C1 C2 1.373(5) . ?
C1 C5 1.424(5) . ?
C2 C3 1.430(4) . ?
C2 C9 1.453(4) . ?
C3 C4 1.331(5) . ?
C3 H3 0.9500 . ?
C4 O1 1.382(4) . ?
C4 H4 0.9500 . ?
C5 O2 1.351(4) . ?
C5 C6 1.363(5) . ?
C6 C7 1.432(4) . ?
C6 C10 1.459(4) . ?
C7 C8 1.342(5) . ?
C7 H7 0.9500 . ?
C8 O2 1.381(4) . ?
C8 H8 0.9500 . ?
C9 O4 1.196(4) . ?
C9 O3 1.392(4) . ?
C10 O5 1.201(4) . ?
C10 O3 1.396(4) . ?
C11 O6 1.350(4) . ?
C11 C12 1.366(5) . ?
C11 C15 1.430(5) . ?
C12 C13 1.432(5) . ?
C12 C19 1.451(5) . ?
C13 C14 1.338(5) . ?
C13 H13 0.9500 . ?
C14 O6 1.377(4) . ?
C14 H14 0.9500 . ?
C15 O7 1.351(4) . ?
C15 C16 1.370(5) . ?
C16 C17 1.430(4) . ?
C16 C20 1.452(5) . ?
C17 C18 1.337(5) . ?
C17 H17 0.9500 . ?
C18 O7 1.383(4) . ?
C18 H18 0.9500 . ?
C19 O9 1.206(4) . ?
C19 O8 1.393(4) . ?
C20 O10 1.203(4) . ?
C20 O8 1.397(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
O1 C1 C2 110.8(3) . . ?
O1 C1 C5 120.9(3) . . ?
C2 C1 C5 128.3(3) . . ?
C1 C2 C3 105.4(3) . . ?
C1 C2 C9 129.9(3) . . ?
C3 C2 C9 124.7(3) . . ?
C4 C3 C2 106.9(3) . . ?
C4 C3 H3 126.5 . . ?
C2 C3 H3 126.5 . . ?
C3 C4 O1 110.8(3) . . ?
C3 C4 H4 124.6 . . ?
O1 C4 H4 124.6 . . ?
O2 C5 C6 110.7(3) . . ?
O2 C5 C1 119.6(3) . . ?
C6 C5 C1 129.7(3) . . ?
C5 C6 C7 106.4(3) . . ?
C5 C6 C10 130.1(3) . . ?
C7 C6 C10 123.5(3) . . ?
C8 C7 C6 105.8(3) . . ?
C8 C7 H7 127.1 . . ?
C6 C7 H7 127.1 . . ?
C7 C8 O2 111.1(3) . . ?
C7 C8 H8 124.4 . . ?
O2 C8 H8 124.4 . . ?
O4 C9 O3 114.3(3) . . ?
O4 C9 C2 123.1(3) . . ?
O3 C9 C2 122.6(3) . . ?
O5 C10 O3 114.6(3) . . ?
O5 C10 C6 123.8(3) . . ?
O3 C10 C6 121.6(3) . . ?
O6 C11 C12 110.7(3) . . ?
O6 C11 C15 119.8(3) . . ?
C12 C11 C15 129.5(3) . . ?
C11 C12 C13 106.2(3) . . ?
C11 C12 C19 130.0(3) . . ?
C13 C12 C19 123.8(3) . . ?
C14 C13 C12 105.8(3) . . ?
C14 C13 H13 127.1 . . ?
C12 C13 H13 127.1 . . ?
C13 C14 O6 111.5(3) . . ?
C13 C14 H14 124.2 . . ?
O6 C14 H14 124.2 . . ?
O7 C15 C16 111.0(3) . . ?
O7 C15 C11 120.5(3) . . ?
C16 C15 C11 128.5(3) . . ?
C15 C16 C17 105.5(3) . . ?
C15 C16 C20 129.9(3) . . ?
C17 C16 C20 124.5(3) . . ?
C18 C17 C16 106.6(3) . . ?
C18 C17 H17 126.7 . . ?
C16 C17 H17 126.7 . . ?
C17 C18 O7 111.0(3) . . ?
C17 C18 H18 124.5 . . ?
O7 C18 H18 124.5 . . ?
O9 C19 O8 114.2(3) . . ?
O9 C19 C12 123.5(3) . . ?
O8 C19 C12 122.3(3) . . ?
O10 C20 O8 114.4(3) . . ?
O10 C20 C16 122.9(3) . . ?
O8 C20 C16 122.6(3) . . ?
C1 O1 C4 106.1(3) . . ?
C5 O2 C8 106.0(3) . . ?
C9 O3 C10 137.4(2) . . ?
C11 O6 C14 105.9(3) . . ?
C15 O7 C18 105.8(3) . . ?
C19 O8 C20 137.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_C6-BFI
_database_code_depnum_ccdc_archive 'CCDC 1839516'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 N O4'
_chemical_formula_sum            'C16 H17 N O4'
_chemical_formula_weight         287.31

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

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

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

_cell_length_a                   12.4217(17)
_cell_length_b                   12.8676(17)
_cell_length_c                   13.2285(18)
_cell_angle_alpha                91.138(2)
_cell_angle_beta                 92.183(2)
_cell_angle_gamma                94.864(2)
_cell_volume                     2104.7(5)
_cell_formula_units_Z            6
_cell_measurement_temperature    173(1)
_cell_measurement_reflns_used    8437
_cell_measurement_theta_min      2.188
_cell_measurement_theta_max      27.991

_exptl_crystal_description       Prizm
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9544
_exptl_absorpt_correction_T_max  0.9712
_exptl_absorpt_process_details   'Bruker SADABS V2.05'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(1)
_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            19501
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         25.00
_reflns_number_total             7278
_reflns_number_gt                6338
_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)+(0.0824P)²+1.0235P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0067(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7278
_refine_ls_number_parameters     572
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1526
_refine_ls_wR_factor_gt          0.1403
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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 -0.11283(17) 0.50510(16) 0.34614(15) 0.0318(5) Uani 1 1 d . . .
C2 C -0.19499(16) 0.57907(15) 0.35483(14) 0.0268(4) Uani 1 1 d . . .
C3 C -0.21753(15) 0.66254(15) 0.29806(14) 0.0267(4) Uani 1 1 d . . .
C4 C -0.16406(16) 0.70186(15) 0.21215(15) 0.0287(4) Uani 1 1 d . . .
C5 C -0.08143(16) 0.66225(16) 0.16433(15) 0.0310(4) Uani 1 1 d . . .
C6 C -0.02443(17) 0.56879(18) 0.18248(16) 0.0357(5) Uani 1 1 d . . .
C7 C -0.33405(17) 0.65275(17) 0.41658(16) 0.0352(5) Uani 1 1 d . . .
H7 H -0.3925 0.6678 0.4572 0.042 Uiso 1 1 calc R . .
C8 C -0.27235(17) 0.57433(16) 0.43217(15) 0.0311(4) Uani 1 1 d . . .
H8 H -0.2786 0.5249 0.4845 0.037 Uiso 1 1 calc R . .
C9 C -0.12525(19) 0.80683(19) 0.08871(18) 0.0432(6) Uani 1 1 d . . .
H9 H -0.1267 0.8637 0.0441 0.052 Uiso 1 1 calc R . .
C10 C -0.05739(18) 0.73220(19) 0.08334(17) 0.0400(5) Uani 1 1 d . . .
H10 H -0.0034 0.7264 0.0351 0.048 Uiso 1 1 calc R . .
C11 C 0.01259(19) 0.40429(18) 0.25856(18) 0.0428(5) Uani 1 1 d . . .
H11A H 0.0227 0.3837 0.1873 0.051 Uiso 1 1 calc R . .
H11B H -0.0298 0.3461 0.2905 0.051 Uiso 1 1 calc R . .
C12 C 0.12115(19) 0.42350(19) 0.31292(18) 0.0422(5) Uani 1 1 d . . .
H12A H 0.1110 0.4364 0.3858 0.051 Uiso 1 1 calc R . .
H12B H 0.1605 0.4865 0.2859 0.051 Uiso 1 1 calc R . .
C13 C 0.18903(19) 0.32895(19) 0.29973(18) 0.0434(6) Uani 1 1 d . . .
H13A H 0.2477 0.3333 0.3528 0.052 Uiso 1 1 calc R . .
H13B H 0.1423 0.2641 0.3099 0.052 Uiso 1 1 calc R . .
C14 C 0.23901(17) 0.32234(16) 0.19583(16) 0.0349(5) Uani 1 1 d . . .
H14A H 0.1802 0.3093 0.1433 0.042 Uiso 1 1 calc R . .
H14B H 0.2786 0.3903 0.1820 0.042 Uiso 1 1 calc R . .
C15 C 0.31605(17) 0.23720(16) 0.18783(17) 0.0358(5) Uani 1 1 d . . .
H15A H 0.3671 0.2429 0.2474 0.043 Uiso 1 1 calc R . .
H15B H 0.2741 0.1684 0.1894 0.043 Uiso 1 1 calc R . .
C16 C 0.3798(2) 0.2426(2) 0.09254(19) 0.0477(6) Uani 1 1 d . . .
H16A H 0.3298 0.2353 0.0332 0.072 Uiso 1 1 calc R . .
H16B H 0.4279 0.1860 0.0916 0.072 Uiso 1 1 calc R . .
H16C H 0.4230 0.3099 0.0911 0.072 Uiso 1 1 calc R . .
N1 N -0.04835(15) 0.49937(14) 0.26152(14) 0.0378(4) Uani 1 1 d . . .
O1 O -0.10295(13) 0.44258(12) 0.41342(12) 0.0452(4) Uani 1 1 d . . .
O2 O 0.04560(14) 0.54943(15) 0.12485(13) 0.0541(5) Uani 1 1 d . . .
O3 O -0.30206(11) 0.70916(11) 0.33406(11) 0.0341(3) Uani 1 1 d . . .
O4 O -0.19278(12) 0.79005(11) 0.16781(11) 0.0369(4) Uani 1 1 d . . .
C17 C 0.50149(15) 0.43404(15) 0.31519(14) 0.0281(4) Uani 1 1 d . . .
C18 C 0.48736(15) 0.51648(15) 0.24196(14) 0.0271(4) Uani 1 1 d . . .
C19 C 0.53951(16) 0.54240(15) 0.15611(15) 0.0279(4) Uani 1 1 d . . .
C20 C 0.62908(16) 0.49715(15) 0.11587(14) 0.0276(4) Uani 1 1 d . . .
C21 C 0.68302(16) 0.41798(15) 0.15338(15) 0.0276(4) Uani 1 1 d . . .
C22 C 0.66437(16) 0.35235(15) 0.24161(14) 0.0285(4) Uani 1 1 d . . .
C23 C 0.41295(17) 0.64831(17) 0.16836(17) 0.0379(5) Uani 1 1 d . . .
H23 H 0.3674 0.7023 0.1539 0.046 Uiso 1 1 calc R . .
C24 C 0.40474(17) 0.58741(16) 0.24878(16) 0.0331(5) Uani 1 1 d . . .
H24 H 0.3540 0.5905 0.3005 0.040 Uiso 1 1 calc R . .
C25 C 0.75997(18) 0.47677(17) 0.01430(17) 0.0369(5) Uani 1 1 d . . .
H25 H 0.8069 0.4858 -0.0405 0.044 Uiso 1 1 calc R . .
C26 C 0.76852(16) 0.40587(16) 0.08608(16) 0.0328(5) Uani 1 1 d . . .
H26 H 0.8214 0.3568 0.0913 0.039 Uiso 1 1 calc R . .
C27 C 0.56222(18) 0.27111(15) 0.37580(15) 0.0332(5) Uani 1 1 d . . .
H27A H 0.5863 0.2074 0.3436 0.040 Uiso 1 1 calc R . .
H27B H 0.4844 0.2573 0.3888 0.040 Uiso 1 1 calc R . .
C28 C 0.62417(17) 0.29104(15) 0.47664(15) 0.0324(5) Uani 1 1 d . . .
H28A H 0.5992 0.3533 0.5107 0.039 Uiso 1 1 calc R . .
H28B H 0.7022 0.3052 0.4648 0.039 Uiso 1 1 calc R . .
C29 C 0.60722(18) 0.19663(16) 0.54513(15) 0.0332(5) Uani 1 1 d . . .
H29A H 0.6332 0.2179 0.6148 0.040 Uiso 1 1 calc R . .
H29B H 0.5287 0.1759 0.5470 0.040 Uiso 1 1 calc R . .
C30 C 0.66429(17) 0.10232(16) 0.51237(15) 0.0317(5) Uani 1 1 d . . .
H30A H 0.7429 0.1227 0.5111 0.038 Uiso 1 1 calc R . .
H30B H 0.6388 0.0812 0.4426 0.038 Uiso 1 1 calc R . .
C31 C 0.64612(18) 0.00850(16) 0.58059(16) 0.0358(5) Uani 1 1 d . . .
H31A H 0.6661 0.0306 0.6514 0.043 Uiso 1 1 calc R . .
H31B H 0.5683 -0.0161 0.5773 0.043 Uiso 1 1 calc R . .
C32 C 0.7114(2) -0.08118(18) 0.5511(2) 0.0491(6) Uani 1 1 d . . .
H32A H 0.6944 -0.1015 0.4801 0.074 Uiso 1 1 calc R . .
H32B H 0.6932 -0.1408 0.5941 0.074 Uiso 1 1 calc R . .
H32C H 0.7887 -0.0592 0.5601 0.074 Uiso 1 1 calc R . .
N2 N 0.57541(13) 0.35794(12) 0.30360(12) 0.0280(4) Uani 1 1 d . . .
O5 O 0.44338(12) 0.42861(13) 0.38725(11) 0.0418(4) Uani 1 1 d . . .
O6 O 0.72766(13) 0.28723(12) 0.26033(12) 0.0441(4) Uani 1 1 d . . .
O7 O 0.49567(12) 0.62271(11) 0.10941(11) 0.0362(4) Uani 1 1 d . . .
O8 O 0.67404(12) 0.53478(11) 0.03060(11) 0.0353(4) Uani 1 1 d . . .
C33 C 0.15176(17) 0.83252(17) 0.25641(16) 0.0344(5) Uani 1 1 d . . .
C34 C 0.07773(16) 0.81830(16) 0.33913(15) 0.0306(4) Uani 1 1 d . . .
C35 C 0.00033(16) 0.87767(16) 0.37242(15) 0.0298(4) Uani 1 1 d . . .
C36 C -0.03359(16) 0.97085(16) 0.33129(15) 0.0303(4) Uani 1 1 d . . .
C37 C 0.00143(16) 1.02109(15) 0.24759(15) 0.0298(4) Uani 1 1 d . . .
C38 C 0.08518(17) 0.99883(16) 0.17714(15) 0.0332(5) Uani 1 1 d . . .
C39 C 0.00303(19) 0.74570(18) 0.47328(18) 0.0415(5) Uani 1 1 d . . .
H39 H -0.0139 0.6998 0.5269 0.050 Uiso 1 1 calc R . .
C40 C 0.07806(17) 0.73206(16) 0.40645(17) 0.0357(5) Uani 1 1 d . . .
H40 H 0.1232 0.6761 0.4037 0.043 Uiso 1 1 calc R . .
C41 C -0.12737(19) 1.10560(18) 0.31426(18) 0.0432(6) Uani 1 1 d . . .
H41 H -0.1782 1.1551 0.3263 0.052 Uiso 1 1 calc R . .
C42 C -0.06104(18) 1.10870(17) 0.23754(17) 0.0374(5) Uani 1 1 d . . .
H42 H -0.0562 1.1593 0.1862 0.045 Uiso 1 1 calc R . .
C43 C 0.2486(2) 0.92627(19) 0.12445(18) 0.0446(6) Uani 1 1 d . . .
H43A H 0.3123 0.8997 0.1595 0.054 Uiso 1 1 calc R . .
H43B H 0.2680 1.0000 0.1079 0.054 Uiso 1 1 calc R . .
C44 C 0.2222(2) 0.86412(19) 0.02833(19) 0.0476(6) Uani 1 1 d . . .
H44A H 0.1570 0.8887 -0.0057 0.057 Uiso 1 1 calc R . .
H44B H 0.2062 0.7897 0.0443 0.057 Uiso 1 1 calc R . .
C45 C 0.3174(2) 0.87531(19) -0.0432(2) 0.0507(6) Uani 1 1 d . . .
H45A H 0.3846 0.8626 -0.0046 0.061 Uiso 1 1 calc R . .
H45B H 0.3054 0.8208 -0.0973 0.061 Uiso 1 1 calc R . .
C46 C 0.33314(19) 0.98093(17) -0.09183(17) 0.0394(5) Uani 1 1 d . . .
H46A H 0.2645 0.9955 -0.1270 0.047 Uiso 1 1 calc R . .
H46B H 0.3493 1.0350 -0.0378 0.047 Uiso 1 1 calc R . .
C47 C 0.4221(2) 0.99037(19) -0.1664(2) 0.0507(6) Uani 1 1 d . . .
H47A H 0.4920 0.9827 -0.1301 0.061 Uiso 1 1 calc R . .
H47B H 0.4098 0.9326 -0.2172 0.061 Uiso 1 1 calc R . .
C48 C 0.4294(3) 1.0925(2) -0.2205(3) 0.0698(9) Uani 1 1 d . . .
H48A H 0.3648 1.0962 -0.2646 0.105 Uiso 1 1 calc R . .
H48B H 0.4938 1.0975 -0.2613 0.105 Uiso 1 1 calc R . .
H48C H 0.4345 1.1503 -0.1707 0.105 Uiso 1 1 calc R . .
N3 N 0.15645(15) 0.92070(14) 0.19368(14) 0.0373(4) Uani 1 1 d . . .
O9 O 0.21547(14) 0.76710(13) 0.24321(13) 0.0496(4) Uani 1 1 d . . .
O10 O 0.09709(14) 1.05354(13) 0.10405(12) 0.0482(4) Uani 1 1 d . . .
O11 O -0.04687(12) 0.83525(12) 0.45448(11) 0.0391(4) Uani 1 1 d . . .
O12 O -0.11256(12) 1.02093(12) 0.37392(12) 0.0403(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.221(2) . ?
C1 N1 1.405(3) . ?
C1 C2 1.460(3) . ?
C2 C3 1.365(3) . ?
C2 C8 1.429(3) . ?
C3 O3 1.350(2) . ?
C3 C4 1.419(3) . ?
C4 O4 1.356(2) . ?
C4 C5 1.356(3) . ?
C5 C10 1.437(3) . ?
C5 C6 1.466(3) . ?
C6 O2 1.217(3) . ?
C6 N1 1.412(3) . ?
C7 C8 1.333(3) . ?
C7 O3 1.375(2) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.333(3) . ?
C9 O4 1.375(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 N1 1.493(3) . ?
C11 C12 1.503(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.549(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.533(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.519(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.513(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 O5 1.217(2) . ?
C17 N2 1.408(3) . ?
C17 C18 1.468(3) . ?
C18 C19 1.362(3) . ?
C18 C24 1.434(3) . ?
C19 O7 1.357(2) . ?
C19 C20 1.415(3) . ?
C20 O8 1.357(2) . ?
C20 C21 1.358(3) . ?
C21 C26 1.428(3) . ?
C21 C22 1.468(3) . ?
C22 O6 1.219(2) . ?
C22 N2 1.407(3) . ?
C23 C24 1.336(3) . ?
C23 O7 1.371(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.337(3) . ?
C25 O8 1.374(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 N2 1.487(2) . ?
C27 C28 1.521(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.535(3) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.520(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.528(3) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.518(3) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 O9 1.218(3) . ?
C33 N3 1.418(3) . ?
C33 C34 1.460(3) . ?
C34 C35 1.358(3) . ?
C34 C40 1.437(3) . ?
C35 O11 1.356(2) . ?
C35 C36 1.416(3) . ?
C36 O12 1.353(2) . ?
C36 C37 1.360(3) . ?
C37 C42 1.427(3) . ?
C37 C38 1.465(3) . ?
C38 O10 1.213(3) . ?
C38 N3 1.410(3) . ?
C39 C40 1.329(3) . ?
C39 O11 1.376(3) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?
C41 C42 1.330(3) . ?
C41 O12 1.379(3) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C43 N3 1.491(3) . ?
C43 C44 1.499(3) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 C45 1.542(3) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 C46 1.516(3) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 C47 1.508(3) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 C48 1.506(3) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 118.61(18) . . ?
O1 C1 C2 118.45(18) . . ?
N1 C1 C2 122.86(17) . . ?
C3 C2 C8 105.40(17) . . ?
C3 C2 C1 131.54(18) . . ?
C8 C2 C1 123.05(18) . . ?
O3 C3 C2 111.13(17) . . ?
O3 C3 C4 120.52(17) . . ?
C2 C3 C4 128.34(18) . . ?
O4 C4 C5 111.21(17) . . ?
O4 C4 C3 120.85(18) . . ?
C5 C4 C3 127.94(19) . . ?
C4 C5 C10 105.16(18) . . ?
C4 C5 C6 131.54(19) . . ?
C10 C5 C6 123.28(19) . . ?
O2 C6 N1 118.7(2) . . ?
O2 C6 C5 117.8(2) . . ?
N1 C6 C5 123.48(18) . . ?
C8 C7 O3 111.17(18) . . ?
C8 C7 H7 124.4 . . ?
O3 C7 H7 124.4 . . ?
C7 C8 C2 106.60(18) . . ?
C7 C8 H8 126.7 . . ?
C2 C8 H8 126.7 . . ?
C10 C9 O4 110.55(19) . . ?
C10 C9 H9 124.7 . . ?
O4 C9 H9 124.7 . . ?
C9 C10 C5 107.02(19) . . ?
C9 C10 H10 126.5 . . ?
C5 C10 H10 126.5 . . ?
N1 C11 C12 111.25(19) . . ?
N1 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
N1 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C13 111.06(19) . . ?
C11 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C12 113.63(18) . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C15 C14 C13 113.26(18) . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C16 C15 C14 113.19(18) . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.8 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 N1 C6 132.71(17) . . ?
C1 N1 C11 113.44(17) . . ?
C6 N1 C11 113.70(17) . . ?
C3 O3 C7 105.69(15) . . ?
C4 O4 C9 106.07(16) . . ?
O5 C17 N2 118.37(18) . . ?
O5 C17 C18 118.37(18) . . ?
N2 C17 C18 123.19(16) . . ?
C19 C18 C24 105.15(17) . . ?
C19 C18 C17 131.85(18) . . ?
C24 C18 C17 122.96(18) . . ?
O7 C19 C18 111.30(17) . . ?
O7 C19 C20 120.83(17) . . ?
C18 C19 C20 127.87(18) . . ?
O8 C20 C21 111.24(17) . . ?
O8 C20 C19 120.43(17) . . ?
C21 C20 C19 128.31(18) . . ?
C20 C21 C26 105.41(17) . . ?
C20 C21 C22 131.42(18) . . ?
C26 C21 C22 123.16(18) . . ?
O6 C22 N2 118.18(18) . . ?
O6 C22 C21 118.18(19) . . ?
N2 C22 C21 123.60(17) . . ?
C24 C23 O7 111.15(18) . . ?
C24 C23 H23 124.4 . . ?
O7 C23 H23 124.4 . . ?
C23 C24 C18 106.71(18) . . ?
C23 C24 H24 126.6 . . ?
C18 C24 H24 126.6 . . ?
C26 C25 O8 110.76(18) . . ?
C26 C25 H25 124.6 . . ?
O8 C25 H25 124.6 . . ?
C25 C26 C21 106.88(18) . . ?
C25 C26 H26 126.6 . . ?
C21 C26 H26 126.6 . . ?
N2 C27 C28 114.65(16) . . ?
N2 C27 H27A 108.6 . . ?
C28 C27 H27A 108.6 . . ?
N2 C27 H27B 108.6 . . ?
C28 C27 H27B 108.6 . . ?
H27A C27 H27B 107.6 . . ?
C27 C28 C29 110.84(17) . . ?
C27 C28 H28A 109.5 . . ?
C29 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C29 C28 H28B 109.5 . . ?
H28A C28 H28B 108.1 . . ?
C30 C29 C28 114.49(17) . . ?
C30 C29 H29A 108.6 . . ?
C28 C29 H29A 108.6 . . ?
C30 C29 H29B 108.6 . . ?
C28 C29 H29B 108.6 . . ?
H29A C29 H29B 107.6 . . ?
C29 C30 C31 114.04(17) . . ?
C29 C30 H30A 108.7 . . ?
C31 C30 H30A 108.7 . . ?
C29 C30 H30B 108.7 . . ?
C31 C30 H30B 108.7 . . ?
H30A C30 H30B 107.6 . . ?
C32 C31 C30 112.80(18) . . ?
C32 C31 H31A 109.0 . . ?
C30 C31 H31A 109.0 . . ?
C32 C31 H31B 109.0 . . ?
C30 C31 H31B 109.0 . . ?
H31A C31 H31B 107.8 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C22 N2 C17 132.07(16) . . ?
C22 N2 C27 113.75(16) . . ?
C17 N2 C27 113.99(16) . . ?
C19 O7 C23 105.70(16) . . ?
C20 O8 C25 105.71(16) . . ?
O9 C33 N3 118.39(19) . . ?
O9 C33 C34 118.17(19) . . ?
N3 C33 C34 123.38(17) . . ?
C35 C34 C40 105.50(18) . . ?
C35 C34 C33 131.38(19) . . ?
C40 C34 C33 123.10(18) . . ?
O11 C35 C34 110.87(18) . . ?
O11 C35 C36 120.85(18) . . ?
C34 C35 C36 128.27(19) . . ?
O12 C36 C37 110.63(18) . . ?
O12 C36 C35 120.91(18) . . ?
C37 C36 C35 128.44(19) . . ?
C36 C37 C42 106.01(18) . . ?
C36 C37 C38 131.39(19) . . ?
C42 C37 C38 122.60(18) . . ?
O10 C38 N3 118.63(19) . . ?
O10 C38 C37 118.41(19) . . ?
N3 C38 C37 122.85(17) . . ?
C40 C39 O11 110.92(19) . . ?
C40 C39 H39 124.5 . . ?
O11 C39 H39 124.5 . . ?
C39 C40 C34 106.71(19) . . ?
C39 C40 H40 126.6 . . ?
C34 C40 H40 126.6 . . ?
C42 C41 O12 111.01(19) . . ?
C42 C41 H41 124.5 . . ?
O12 C41 H41 124.5 . . ?
C41 C42 C37 106.47(19) . . ?
C41 C42 H42 126.8 . . ?
C37 C42 H42 126.8 . . ?
N3 C43 C44 112.12(19) . . ?
N3 C43 H43A 109.2 . . ?
C44 C43 H43A 109.2 . . ?
N3 C43 H43B 109.2 . . ?
C44 C43 H43B 109.2 . . ?
H43A C43 H43B 107.9 . . ?
C43 C44 C45 110.7(2) . . ?
C43 C44 H44A 109.5 . . ?
C45 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
C45 C44 H44B 109.5 . . ?
H44A C44 H44B 108.1 . . ?
C46 C45 C44 114.3(2) . . ?
C46 C45 H45A 108.7 . . ?
C44 C45 H45A 108.7 . . ?
C46 C45 H45B 108.7 . . ?
C44 C45 H45B 108.7 . . ?
H45A C45 H45B 107.6 . . ?
C47 C46 C45 114.52(19) . . ?
C47 C46 H46A 108.6 . . ?
C45 C46 H46A 108.6 . . ?
C47 C46 H46B 108.6 . . ?
C45 C46 H46B 108.6 . . ?
H46A C46 H46B 107.6 . . ?
C48 C47 C46 113.4(2) . . ?
C48 C47 H47A 108.9 . . ?
C46 C47 H47A 108.9 . . ?
C48 C47 H47B 108.9 . . ?
C46 C47 H47B 108.9 . . ?
H47A C47 H47B 107.7 . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C38 N3 C33 132.30(17) . . ?
C38 N3 C43 113.45(17) . . ?
C33 N3 C43 113.93(17) . . ?
C35 O11 C39 106.00(17) . . ?
C36 O12 C41 105.88(16) . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.621
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.078
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_S67-4b
_database_code_depnum_ccdc_archive 'CCDC 1839514'
_audit_update_record             
;
2018-04-25 deposited with the CCDC.
2018-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
# start Validation Reply Form
_vrf_PLAT770_S67-4b              
;
PROBLEM: Suspect C-H Bond in CIF:  C14A     --H16F      .       1.32 Ang.  
RESPONSE: Its do to the disorder hexane moiety.
;
# end Validation Reply Form

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H15 Br2 N O4'
_chemical_formula_sum            'C16 H15 Br2 N O4'
_chemical_formula_weight         445.11

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc '

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                   8.962(1)
_cell_length_b                   22.105(4)
_cell_length_c                   8.691(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.837(3)
_cell_angle_gamma                90.00
_cell_volume                     1664.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    292(1)
_cell_measurement_reflns_used    4884
_cell_measurement_theta_min      2.351
_cell_measurement_theta_max      23.991

_exptl_crystal_description       Yellow
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    4.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1854
_exptl_absorpt_correction_T_max  0.5915
_exptl_absorpt_process_details   'Bruker SADABS V2.05'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      292(1)
_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            17960
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         26.99
_reflns_number_total             3630
_reflns_number_gt                2748
_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)+(0.0462P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3630
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0849
_refine_ls_wR_factor_gt          0.0802
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.53063(3) 0.246474(13) 0.96482(4) 0.05807(12) Uani 1 1 d . . .
Br2 Br 0.06895(4) 0.449465(12) 0.68289(4) 0.06569(13) Uani 1 1 d . . .
C1 C -0.0860(3) 0.13905(12) 0.7421(3) 0.0513(6) Uani 1 1 d . B .
C2 C -0.1822(3) 0.18575(11) 0.7889(3) 0.0447(6) Uani 1 1 d . . .
C3 C -0.1726(3) 0.24751(10) 0.7867(3) 0.0413(6) Uani 1 1 d . . .
C4 C -0.0676(3) 0.28411(11) 0.7331(3) 0.0422(6) Uani 1 1 d . . .
C5 C 0.0484(3) 0.26639(12) 0.6688(3) 0.0450(6) Uani 1 1 d . . .
C6 C 0.1007(3) 0.20610(12) 0.6341(3) 0.0479(6) Uani 1 1 d . B .
C7 C -0.3651(3) 0.22458(12) 0.8856(3) 0.0478(6) Uani 1 1 d . . .
C8 C -0.3076(3) 0.17202(12) 0.8542(3) 0.0495(6) Uani 1 1 d . . .
H8 H -0.3429 0.1337 0.8717 0.059 Uiso 1 1 calc R . .
C9 C 0.0448(3) 0.36589(12) 0.6833(3) 0.0487(6) Uani 1 1 d . . .
C10 C 0.1218(3) 0.32077(12) 0.6373(3) 0.0494(6) Uani 1 1 d . . .
H10 H 0.2060 0.3239 0.5936 0.059 Uiso 1 1 calc R . .
C11 C 0.1120(4) 0.09664(13) 0.6288(4) 0.0678(9) Uani 1 1 d . B .
H11A H 0.0375 0.0640 0.6027 0.081 Uiso 1 1 calc R . .
H11B H 0.1499 0.1046 0.5358 0.081 Uiso 1 1 calc R . .
C12 C 0.2428(5) 0.07759(17) 0.7626(5) 0.0921(12) Uani 1 1 d . . .
H12A H 0.2093 0.0702 0.8587 0.110 Uiso 1 1 calc R A 1
H12B H 0.3246 0.1075 0.7845 0.110 Uiso 1 1 calc R A 1
C13A C 0.2973(14) 0.0153(6) 0.6933(13) 0.130(4) Uani 0.65 1 d P B 1
H13A H 0.2061 -0.0076 0.6414 0.156 Uiso 0.65 1 calc PR B 1
H13B H 0.3506 0.0257 0.6128 0.156 Uiso 0.65 1 calc PR B 1
C14A C 0.3881(18) -0.0195(5) 0.8001(13) 0.172(5) Uani 0.65 1 d P B 1
H14A H 0.3335 -0.0260 0.8817 0.206 Uiso 0.65 1 calc PR B 1
H14B H 0.4768 0.0054 0.8488 0.206 Uiso 0.65 1 calc PR B 1
C15A C 0.4555(14) -0.0824(4) 0.7729(19) 0.110(3) Uani 0.65 1 d P B 1
H15A H 0.5482 -0.0903 0.8568 0.132 Uiso 0.65 1 calc PR B 1
H15B H 0.3809 -0.1138 0.7767 0.132 Uiso 0.65 1 calc PR B 1
C16A C 0.4923(19) -0.0836(4) 0.6177(17) 0.137(4) Uani 0.65 1 d P B 1
H16A H 0.4005 -0.0918 0.5352 0.205 Uiso 0.65 1 d PR B 1
H16B H 0.5672 -0.1147 0.6179 0.205 Uiso 0.65 1 d PR B 1
H16C H 0.5338 -0.0451 0.5987 0.205 Uiso 0.65 1 d PR B 1
C13B C 0.3835(13) 0.0377(5) 0.7497(18) 0.065(3) Uani 0.35 1 d P B 2
H13C H 0.4519 0.0294 0.8536 0.078 Uiso 0.35 1 calc PR B 2
H13D H 0.4417 0.0565 0.6826 0.078 Uiso 0.35 1 calc PR B 2
C14B C 0.2934(18) -0.0250(7) 0.666(3) 0.122(7) Uani 0.35 1 d P B 2
H14C H 0.2418 -0.0433 0.7398 0.146 Uiso 0.35 1 calc PR B 2
H14D H 0.2144 -0.0134 0.5717 0.146 Uiso 0.35 1 calc PR B 2
C15B C 0.3949(17) -0.0722(6) 0.619(3) 0.109(6) Uani 0.35 1 d P B 2
H15C H 0.3389 -0.1099 0.5923 0.131 Uiso 0.35 1 calc PR B 2
H15D H 0.4287 -0.0587 0.5271 0.131 Uiso 0.35 1 calc PR B 2
C16B C 0.518(5) -0.080(3) 0.746(6) 0.30(3) Uani 0.35 1 d P B 2
H16D H 0.6113 -0.0826 0.7113 0.446 Uiso 0.35 1 d PR B 2
H16E H 0.5056 -0.1161 0.8024 0.446 Uiso 0.35 1 d PR B 2
H16F H 0.5230 -0.0456 0.8142 0.446 Uiso 0.35 1 d PR B 2
N1 N 0.0339(3) 0.15211(9) 0.6689(2) 0.0491(5) Uani 1 1 d . . .
O1 O -0.1132(3) 0.08654(9) 0.7665(3) 0.0749(6) Uani 1 1 d . . .
O2 O 0.2064(3) 0.20331(9) 0.5712(3) 0.0679(6) Uani 1 1 d . . .
O3 O -0.2840(2) 0.27267(7) 0.8468(2) 0.0465(4) Uani 1 1 d . . .
O4 O -0.0728(2) 0.34528(7) 0.7434(2) 0.0478(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C7 1.853(3) . ?
Br2 C9 1.860(3) . ?
C1 O1 1.216(3) . ?
C1 N1 1.412(4) . ?
C1 C2 1.467(4) . ?
C2 C3 1.368(3) . ?
C2 C8 1.416(4) . ?
C3 O3 1.359(3) . ?
C3 C4 1.408(4) . ?
C4 O4 1.357(3) . ?
C4 C5 1.357(4) . ?
C5 C10 1.430(4) . ?
C5 C6 1.469(4) . ?
C6 O2 1.211(3) . ?
C6 N1 1.402(3) . ?
C7 C8 1.327(4) . ?
C7 O3 1.377(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.331(4) . ?
C9 O4 1.369(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.485(5) . ?
C11 N1 1.497(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13B 1.567(11) . ?
C12 C13A 1.627(12) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13A C14A 1.315(12) . ?
C13A H13A 0.9700 . ?
C13A H13B 0.9700 . ?
C14A C15A 1.559(14) . ?
C14A H14A 0.9700 . ?
C14A H14B 0.9700 . ?
C14A H16F 1.3166 . ?
C15A C16A 1.47(2) . ?
C15A H15A 0.9700 . ?
C15A H15B 0.9700 . ?
C15A H16E 0.8731 . ?
C15A H16F 1.0229 . ?
C16A H16A 0.9600 . ?
C16A H16B 0.9600 . ?
C16A H16C 0.9600 . ?
C16A H16D 1.1641 . ?
C13B C14B 1.674(17) . ?
C13B H13C 0.9700 . ?
C13B H13D 0.9700 . ?
C14B C15B 1.51(2) . ?
C14B H14C 0.9700 . ?
C14B H14D 0.9700 . ?
C15B C16B 1.35(5) . ?
C15B H16A 0.8589 . ?
C15B H16C 1.4315 . ?
C15B H15C 0.9700 . ?
C15B H15D 0.9700 . ?
C16B H16B 1.5064 . ?
C16B H16C 1.5287 . ?
C16B H16D 0.9600 . ?
C16B H16E 0.9600 . ?
C16B H16F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 118.9(2) . . ?
O1 C1 C2 117.7(3) . . ?
N1 C1 C2 123.4(2) . . ?
C3 C2 C8 106.1(2) . . ?
C3 C2 C1 130.9(2) . . ?
C8 C2 C1 122.9(2) . . ?
O3 C3 C2 110.4(2) . . ?
O3 C3 C4 120.8(2) . . ?
C2 C3 C4 128.9(2) . . ?
O4 C4 C5 110.9(2) . . ?
O4 C4 C3 120.9(2) . . ?
C5 C4 C3 128.1(2) . . ?
C4 C5 C10 105.9(2) . . ?
C4 C5 C6 131.6(2) . . ?
C10 C5 C6 122.4(2) . . ?
O2 C6 N1 118.7(2) . . ?
O2 C6 C5 117.8(2) . . ?
N1 C6 C5 123.5(2) . . ?
C8 C7 O3 111.6(2) . . ?
C8 C7 Br1 134.0(2) . . ?
O3 C7 Br1 114.33(19) . . ?
C7 C8 C2 106.5(2) . . ?
C7 C8 H8 126.7 . . ?
C2 C8 H8 126.7 . . ?
C10 C9 O4 112.0(2) . . ?
C10 C9 Br2 132.4(2) . . ?
O4 C9 Br2 115.63(18) . . ?
C9 C10 C5 105.8(2) . . ?
C9 C10 H10 127.1 . . ?
C5 C10 H10 127.1 . . ?
C12 C11 N1 111.8(3) . . ?
C12 C11 H11A 109.2 . . ?
N1 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
N1 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C11 C12 C13B 126.3(6) . . ?
C11 C12 C13A 101.6(5) . . ?
C13B C12 C13A 34.2(5) . . ?
C11 C12 H12A 111.4 . . ?
C13B C12 H12A 113.5 . . ?
C13A C12 H12A 111.4 . . ?
C11 C12 H12B 111.4 . . ?
C13B C12 H12B 79.4 . . ?
C13A C12 H12B 111.4 . . ?
H12A C12 H12B 109.3 . . ?
C14A C13A C12 115.0(11) . . ?
C14A C13A H13A 108.5 . . ?
C12 C13A H13A 108.5 . . ?
C14A C13A H13B 108.5 . . ?
C12 C13A H13B 108.5 . . ?
H13A C13A H13B 107.5 . . ?
C13A C14A C15A 127.5(13) . . ?
C13A C14A H14A 105.4 . . ?
C15A C14A H14A 105.4 . . ?
C13A C14A H14B 105.4 . . ?
C15A C14A H14B 105.4 . . ?
H14A C14A H14B 106.0 . . ?
C13A C14A H16F 135.2 . . ?
C15A C14A H16F 40.6 . . ?
H14A C14A H16F 119.3 . . ?
H14B C14A H16F 65.0 . . ?
C16A C15A C14A 110.0(9) . . ?
C16A C15A H15A 109.7 . . ?
C14A C15A H15A 109.7 . . ?
C16A C15A H15B 109.7 . . ?
C14A C15A H15B 109.7 . . ?
H15A C15A H15B 108.2 . . ?
C16A C15A H16E 92.0 . . ?
C14A C15A H16E 155.1 . . ?
H15A C15A H16E 49.5 . . ?
H15B C15A H16E 71.7 . . ?
C16A C15A H16F 94.9 . . ?
C14A C15A H16F 56.9 . . ?
H15A C15A H16F 64.1 . . ?
H15B C15A H16F 155.3 . . ?
H16E C15A H16F 111.3 . . ?
C15A C16A H16A 109.7 . . ?
C15A C16A H16B 109.4 . . ?
H16A C16A H16B 109.5 . . ?
C15A C16A H16C 109.2 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C15A C16A H16D 74.8 . . ?
H16A C16A H16D 169.3 . . ?
H16B C16A H16D 59.9 . . ?
H16C C16A H16D 77.1 . . ?
C12 C13B C14B 100.9(8) . . ?
C12 C13B H13C 111.6 . . ?
C14B C13B H13C 111.6 . . ?
C12 C13B H13D 111.6 . . ?
C14B C13B H13D 111.6 . . ?
H13C C13B H13D 109.4 . . ?
C15B C14B C13B 115.6(12) . . ?
C15B C14B H14C 108.4 . . ?
C13B C14B H14C 108.4 . . ?
C15B C14B H14D 108.4 . . ?
C13B C14B H14D 108.4 . . ?
H14C C14B H14D 107.4 . . ?
C16B C15B C14B 107(3) . . ?
C16B C15B H16A 114.4 . . ?
C14B C15B H16A 138.4 . . ?
C16B C15B H16C 66.5 . . ?
C14B C15B H16C 110.4 . . ?
H16A C15B H16C 82.3 . . ?
C16B C15B H15C 110.4 . . ?
C14B C15B H15C 110.4 . . ?
H16A C15B H15C 60.2 . . ?
H16C C15B H15C 137.9 . . ?
C16B C15B H15D 110.4 . . ?
C14B C15B H15D 110.4 . . ?
H16A C15B H15D 50.2 . . ?
H16C C15B H15D 46.1 . . ?
H15C C15B H15D 108.6 . . ?
C15B C16B H16B 78.3 . . ?
C15B C16B H16C 59.2 . . ?
H16B C16B H16C 62.2 . . ?
C15B C16B H16D 110.4 . . ?
H16B C16B H16D 45.3 . . ?
H16C C16B H16D 59.7 . . ?
C15B C16B H16E 110.3 . . ?
H16B C16B H16E 92.8 . . ?
H16C C16B H16E 153.7 . . ?
H16D C16B H16E 109.5 . . ?
C15B C16B H16F 107.7 . . ?
H16B C16B H16F 152.2 . . ?
H16C C16B H16F 96.9 . . ?
H16D C16B H16F 109.5 . . ?
H16E C16B H16F 109.5 . . ?
C6 N1 C1 133.4(2) . . ?
C6 N1 C11 113.3(2) . . ?
C1 N1 C11 113.1(2) . . ?
C3 O3 C7 105.29(19) . . ?
C4 O4 C9 105.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.575
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.066
