# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 F N O3'
_chemical_formula_sum            'C20 H14 F N O3'
_chemical_formula_weight         335.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   8.972(3)
_cell_length_b                   7.295(3)
_cell_length_c                   24.757(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.902(7)
_cell_angle_gamma                90.00
_cell_volume                     1608.8(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3789
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      28

_exptl_crystal_description       rectangular
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17298
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.66
_diffrn_reflns_theta_max         28.00
_reflns_number_total             3789
_reflns_number_gt                2575
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1999)'
_computing_publication_material  WinGX

_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 > 2σ(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)+(0.0673P)²+0.1405P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3789
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1558
_refine_ls_wR_factor_gt          0.1392
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_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
F1 F 1.20767(15) 0.1750(2) 0.77540(6) 0.1059(5) Uani 1 1 d . . .
N1 N 0.54396(17) 0.3371(2) 1.11696(6) 0.0604(4) Uani 1 1 d . . .
O2 O 0.28967(15) 0.3218(2) 1.10279(6) 0.0758(4) Uani 1 1 d . . .
O1 O 0.79791(15) 0.3415(2) 1.13142(5) 0.0763(4) Uani 1 1 d . . .
O3 O 0.70079(14) 0.1749(2) 0.87692(5) 0.0786(4) Uani 1 1 d . . .
C1 C 0.69156(18) 0.2829(2) 1.04134(7) 0.0513(4) Uani 1 1 d . . .
C2 C 0.8269(2) 0.2737(3) 1.02090(8) 0.0624(5) Uani 1 1 d . . .
H2 H 0.921(2) 0.287(3) 1.0457(8) 0.072(5) Uiso 1 1 d . . .
C3 C 0.8344(2) 0.2381(3) 0.96598(8) 0.0674(5) Uani 1 1 d . . .
H3 H 0.928(2) 0.229(3) 0.9525(8) 0.070(5) Uiso 1 1 d . . .
C4 C 0.70558(19) 0.2111(3) 0.93119(7) 0.0589(4) Uani 1 1 d . . .
C9 C 0.56209(18) 0.2175(2) 0.95030(7) 0.0514(4) Uani 1 1 d . . .
C5 C 0.4264(2) 0.1896(3) 0.91595(8) 0.0597(5) Uani 1 1 d . . .
H5 H 0.430(2) 0.164(2) 0.8792(8) 0.069(6) Uiso 1 1 d . . .
C6 C 0.2922(2) 0.1978(3) 0.93710(8) 0.0661(5) Uani 1 1 d . . .
H6 H 0.202(2) 0.175(3) 0.9132(8) 0.077(6) Uiso 1 1 d . . .
C7 C 0.2875(2) 0.2357(3) 0.99173(8) 0.0612(5) Uani 1 1 d . . .
H7 H 0.199(2) 0.244(3) 1.0069(7) 0.069(5) Uiso 1 1 d . . .
C8 C 0.41688(17) 0.2646(2) 1.02612(7) 0.0508(4) Uani 1 1 d . . .
C10 C 0.55756(17) 0.2552(2) 1.00595(6) 0.0476(4) Uani 1 1 d . . .
C11 C 0.6860(2) 0.3216(2) 1.09919(7) 0.0579(4) Uani 1 1 d . . .
C12 C 0.4089(2) 0.3086(2) 1.08402(7) 0.0569(4) Uani 1 1 d . . .
C13 C 0.5370(3) 0.3878(4) 1.17465(8) 0.0763(6) Uani 1 1 d . . .
H13A H 0.443(2) 0.462(3) 1.1758(8) 0.095(7) Uiso 1 1 d . . .
H13B H 0.622(3) 0.473(3) 1.1855(9) 0.100(7) Uiso 1 1 d . . .
C14 C 0.5335(4) 0.2222(5) 1.21067(11) 0.0954(8) Uani 1 1 d . . .
H14A H 0.445(4) 0.146(4) 1.1979(12) 0.133(11) Uiso 1 1 d . . .
H14B H 0.534(3) 0.263(4) 1.2480(13) 0.122(9) Uiso 1 1 d . . .
H14C H 0.622(3) 0.152(4) 1.2086(10) 0.117(10) Uiso 1 1 d . . .
C15 C 0.8356(2) 0.1768(3) 0.85336(7) 0.0626(5) Uani 1 1 d . . .
C16 C 0.8924(2) 0.3407(3) 0.83800(8) 0.0693(5) Uani 1 1 d . . .
H16 H 0.846(2) 0.452(3) 0.8456(8) 0.084(6) Uiso 1 1 d . . .
C17 C 1.0193(2) 0.3397(3) 0.81148(8) 0.0699(5) Uani 1 1 d . . .
H17 H 1.061(2) 0.451(3) 0.8000(8) 0.087(6) Uiso 1 1 d . . .
C18 C 1.0825(2) 0.1750(3) 0.80150(7) 0.0678(5) Uani 1 1 d . . .
C19 C 1.0282(2) 0.0109(3) 0.81702(8) 0.0722(5) Uani 1 1 d . . .
H19 H 1.076(2) -0.105(3) 0.8093(8) 0.093(7) Uiso 1 1 d . . .
C20 C 0.9020(2) 0.0110(3) 0.84368(8) 0.0691(5) Uani 1 1 d . . .
H20 H 0.855(2) -0.101(3) 0.8539(8) 0.083(6) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
F1 C18 1.361(2) . ?
N1 C12 1.392(2) . ?
N1 C11 1.402(2) . ?
N1 C13 1.484(2) . ?
O2 C12 1.220(2) . ?
O1 C11 1.214(2) . ?
O3 C4 1.365(2) . ?
O3 C15 1.405(2) . ?
C1 C2 1.372(2) . ?
C1 C10 1.415(2) . ?
C1 C11 1.466(2) . ?
C2 C3 1.394(3) . ?
C2 H2 0.99(2) . ?
C3 C4 1.370(3) . ?
C3 H3 0.94(2) . ?
C4 C9 1.425(2) . ?
C9 C10 1.410(2) . ?
C9 C5 1.414(2) . ?
C5 C6 1.371(3) . ?
C5 H5 0.933(19) . ?
C6 C7 1.386(3) . ?
C6 H6 0.96(2) . ?
C7 C8 1.371(2) . ?
C7 H7 0.92(2) . ?
C8 C10 1.414(2) . ?
C8 C12 1.479(2) . ?
C13 C14 1.504(4) . ?
C13 H13A 1.01(2) . ?
C13 H13B 1.00(2) . ?
C14 H14A 0.99(3) . ?
C14 H14B 0.97(3) . ?
C14 H14C 0.95(3) . ?
C15 C16 1.372(3) . ?
C15 C20 1.382(3) . ?
C16 C17 1.381(3) . ?
C16 H16 0.94(2) . ?
C17 C18 1.364(3) . ?
C17 H17 0.95(2) . ?
C18 C19 1.365(3) . ?
C19 C20 1.378(3) . ?
C19 H19 0.98(2) . ?
C20 H20 0.97(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N1 C11 124.34(15) . . ?
C12 N1 C13 117.83(16) . . ?
C11 N1 C13 117.84(16) . . ?
C4 O3 C15 118.69(14) . . ?
C2 C1 C10 119.25(16) . . ?
C2 C1 C11 120.34(15) . . ?
C10 C1 C11 120.42(15) . . ?
C1 C2 C3 121.15(17) . . ?
C1 C2 H2 119.6(11) . . ?
C3 C2 H2 119.2(11) . . ?
C4 C3 C2 120.27(17) . . ?
C4 C3 H3 119.1(11) . . ?
C2 C3 H3 120.6(11) . . ?
O3 C4 C3 124.82(16) . . ?
O3 C4 C9 114.23(15) . . ?
C3 C4 C9 120.95(17) . . ?
C10 C9 C5 119.47(15) . . ?
C10 C9 C4 117.65(15) . . ?
C5 C9 C4 122.88(16) . . ?
C6 C5 C9 119.76(18) . . ?
C6 C5 H5 121.3(12) . . ?
C9 C5 H5 118.9(12) . . ?
C5 C6 C7 120.85(18) . . ?
C5 C6 H6 118.2(12) . . ?
C7 C6 H6 120.9(11) . . ?
C8 C7 C6 120.91(17) . . ?
C8 C7 H7 116.3(12) . . ?
C6 C7 H7 122.7(12) . . ?
C7 C8 C10 119.90(17) . . ?
C7 C8 C12 119.95(15) . . ?
C10 C8 C12 120.14(15) . . ?
C9 C10 C8 119.10(15) . . ?
C9 C10 C1 120.73(15) . . ?
C8 C10 C1 120.17(16) . . ?
O1 C11 N1 119.71(16) . . ?
O1 C11 C1 122.83(16) . . ?
N1 C11 C1 117.46(15) . . ?
O2 C12 N1 120.42(17) . . ?
O2 C12 C8 122.19(17) . . ?
N1 C12 C8 117.39(14) . . ?
N1 C13 C14 112.1(2) . . ?
N1 C13 H13A 107.1(12) . . ?
C14 C13 H13A 109.7(13) . . ?
N1 C13 H13B 107.1(13) . . ?
C14 C13 H13B 114.3(14) . . ?
H13A C13 H13B 106.1(19) . . ?
C13 C14 H14A 109.6(17) . . ?
C13 C14 H14B 108.6(19) . . ?
H14A C14 H14B 113(2) . . ?
C13 C14 H14C 108.7(17) . . ?
H14A C14 H14C 109(3) . . ?
H14B C14 H14C 108(2) . . ?
C16 C15 C20 122.19(18) . . ?
C16 C15 O3 119.39(18) . . ?
C20 C15 O3 118.32(18) . . ?
C15 C16 C17 118.8(2) . . ?
C15 C16 H16 120.6(13) . . ?
C17 C16 H16 120.5(13) . . ?
C18 C17 C16 118.4(2) . . ?
C18 C17 H17 120.8(13) . . ?
C16 C17 H17 120.8(13) . . ?
F1 C18 C17 118.06(19) . . ?
F1 C18 C19 118.45(19) . . ?
C17 C18 C19 123.48(19) . . ?
C18 C19 C20 118.4(2) . . ?
C18 C19 H19 121.5(14) . . ?
C20 C19 H19 120.1(14) . . ?
C19 C20 C15 118.7(2) . . ?
C19 C20 H20 122.5(12) . . ?
C15 C20 H20 118.7(12) . . ?

_diffrn_measured_fraction_theta_max 0.965
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.965
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.094
_database_code_depnum_ccdc_archive 'CCDC 961304'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 Br N O3'
_chemical_formula_sum            'C20 H14 Br N O3'
_chemical_formula_weight         396.23

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   'P 21/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                   9.008(7)
_cell_length_b                   7.848(6)
_cell_length_c                   24.086(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.229(13)
_cell_angle_gamma                90.00
_cell_volume                     1676(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3736
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      27.25

_exptl_crystal_description       rectangular
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    2.472
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.337
_exptl_absorpt_correction_T_max  0.526
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14934
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_av_sigmaI/netI    0.0770
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         27.25
_reflns_number_total             3736
_reflns_number_gt                2094
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1999)'
_computing_publication_material  WinGX

_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 > 2σ(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)+(0.1132P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3736
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1291
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.1889
_refine_ls_wR_factor_gt          0.1558
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_restrained_S_all      0.954
_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
O2 O 0.3058(4) 0.0866(4) 0.10452(16) 0.0623(9) Uani 1 1 d . . .
C9 C 0.5621(5) 0.3101(5) -0.03840(16) 0.0424(10) Uani 1 1 d . . .
C11 C 0.7012(6) 0.1064(5) 0.10511(19) 0.0459(10) Uani 1 1 d . . .
C8 C 0.4254(5) 0.2023(5) 0.03293(17) 0.0426(10) Uani 1 1 d . . .
C12 C 0.4233(6) 0.1170(5) 0.0879(2) 0.0487(11) Uani 1 1 d . . .
C10 C 0.5619(5) 0.2335(5) 0.01521(16) 0.0387(9) Uani 1 1 d . . .
C2 C 0.8325(5) 0.2196(6) 0.03165(19) 0.0502(11) Uani 1 1 d . . .
H2 H 0.917(5) 0.1934(18) 0.0533(14) 0.060 Uiso 1 1 calc R . .
O1 O 0.8152(4) 0.0689(4) 0.13666(15) 0.0634(10) Uani 1 1 d . . .
C5 C 0.4230(6) 0.3567(6) -0.0716(2) 0.0501(11) Uani 1 1 d . . .
H5 H 0.4212(6) 0.408(3) -0.105(2) 0.060 Uiso 1 1 calc R . .
C1 C 0.6997(5) 0.1884(5) 0.04946(17) 0.0428(10) Uani 1 1 d . . .
C6 C 0.2912(6) 0.3238(6) -0.0533(2) 0.0559(12) Uani 1 1 d . . .
H6 H 0.205(6) 0.3513(19) -0.0746(14) 0.067 Uiso 1 1 calc R . .
C13 C 0.5619(7) -0.0106(7) 0.1749(2) 0.0662(15) Uani 1 1 d . . .
H13A H 0.641(3) -0.082(3) 0.1821(4) 0.079 Uiso 1 1 calc R . .
H13B H 0.477(4) -0.072(3) 0.1732(2) 0.079 Uiso 1 1 calc R . .
C7 C 0.2914(6) 0.2460(5) -0.0005(2) 0.0528(11) Uani 1 1 d . . .
H7 H 0.198(5) 0.2238(14) 0.0119(8) 0.063 Uiso 1 1 calc R . .
C3 C 0.8338(6) 0.2935(7) -0.02127(18) 0.0550(12) Uani 1 1 d . . .
H3 H 0.917(6) 0.3100(14) -0.0323(8) 0.066 Uiso 1 1 calc R . .
N1 N 0.5607(5) 0.0745(4) 0.11984(16) 0.0479(9) Uani 1 1 d . . .
C4 C 0.7024(6) 0.3391(6) -0.05516(18) 0.0486(11) Uani 1 1 d . . .
C14 C 0.5720(9) 0.1180(9) 0.2223(2) 0.087(2) Uani 1 1 d . . .
H14A H 0.574(6) 0.055(3) 0.2600(17) 0.130 Uiso 1 1 calc R . .
H14B H 0.480(5) 0.198(6) 0.2148(12) 0.130 Uiso 1 1 calc R . .
H14C H 0.669(5) 0.189(5) 0.2245(14) 0.130 Uiso 1 1 calc R . .
O3 O 0.6932(4) 0.4153(5) -0.10704(13) 0.0614(9) Uani 1 1 d . . .
C20 C 0.8753(6) 0.2640(6) -0.14954(17) 0.0480(11) Uani 1 1 d . . .
H20 H 0.835(2) 0.162(6) -0.1407(5) 0.058 Uiso 1 1 calc R . .
C15 C 0.8191(6) 0.4141(6) -0.13345(18) 0.0499(11) Uani 1 1 d . . .
C19 C 0.9930(5) 0.2670(6) -0.17912(17) 0.0459(10) Uani 1 1 d . . .
H19 H 1.031(2) 0.171(6) -0.1898(6) 0.055 Uiso 1 1 calc R . .
C17 C 0.9924(6) 0.5750(6) -0.1756(2) 0.0534(11) Uani 1 1 d . . .
H17 H 1.034(2) 0.684(6) -0.1848(5) 0.064 Uiso 1 1 calc R . .
C16 C 0.8749(6) 0.5698(6) -0.14627(19) 0.0536(12) Uani 1 1 d . . .
H16 H 0.837(3) 0.660(6) -0.1363(7) 0.064 Uiso 1 1 calc R . .
C18 C 1.0497(6) 0.4241(5) -0.19175(17) 0.0460(10) Uani 1 1 d . . .
Br1 Br 1.21441(7) 0.42851(8) -0.23095(2) 0.0695(3) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O2 C12 1.219(6) . ?
C9 C5 1.410(6) . ?
C9 C4 1.412(7) . ?
C9 C10 1.424(6) . ?
C11 O1 1.201(6) . ?
C11 N1 1.397(6) . ?
C11 C1 1.485(6) . ?
C8 C7 1.370(6) . ?
C8 C10 1.393(6) . ?
C8 C12 1.488(7) . ?
C12 N1 1.377(6) . ?
C10 C1 1.408(6) . ?
C2 C1 1.363(7) . ?
C2 C3 1.403(7) . ?
C2 H2 0.8693 . ?
C5 C6 1.362(7) . ?
C5 H5 0.8984 . ?
C6 C7 1.410(7) . ?
C6 H6 0.8770 . ?
C13 N1 1.484(6) . ?
C13 C14 1.514(9) . ?
C13 H13A 0.8988 . ?
C13 H13B 0.8988 . ?
C7 H7 0.9561 . ?
C3 C4 1.361(7) . ?
C3 H3 0.8501 . ?
C4 O3 1.375(6) . ?
C14 H14A 1.0310 . ?
C14 H14B 1.0310 . ?
C14 H14C 1.0310 . ?
O3 C15 1.395(6) . ?
C20 C15 1.365(7) . ?
C20 C19 1.379(7) . ?
C20 H20 0.9174 . ?
C15 C16 1.377(7) . ?
C19 C18 1.389(6) . ?
C19 H19 0.8843 . ?
C17 C16 1.374(7) . ?
C17 C18 1.375(6) . ?
C17 H17 0.9745 . ?
C16 H16 0.8407 . ?
C18 Br1 1.895(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C9 C4 123.1(4) . . ?
C5 C9 C10 118.6(4) . . ?
C4 C9 C10 118.2(4) . . ?
O1 C11 N1 120.5(4) . . ?
O1 C11 C1 123.2(5) . . ?
N1 C11 C1 116.3(4) . . ?
C7 C8 C10 120.6(4) . . ?
C7 C8 C12 119.1(4) . . ?
C10 C8 C12 120.3(4) . . ?
O2 C12 N1 121.1(5) . . ?
O2 C12 C8 121.9(4) . . ?
N1 C12 C8 117.0(4) . . ?
C8 C10 C1 120.7(4) . . ?
C8 C10 C9 119.7(4) . . ?
C1 C10 C9 119.6(4) . . ?
C1 C2 C3 120.7(4) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C6 C5 C9 120.3(5) . . ?
C6 C5 H5 119.8 . . ?
C9 C5 H5 119.8 . . ?
C2 C1 C10 120.2(4) . . ?
C2 C1 C11 119.6(4) . . ?
C10 C1 C11 120.2(4) . . ?
C5 C6 C7 120.8(5) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
N1 C13 C14 111.4(4) . . ?
N1 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
N1 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C8 C7 C6 119.9(5) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C4 C3 C2 120.5(5) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C12 N1 C11 125.5(4) . . ?
C12 N1 C13 118.1(4) . . ?
C11 N1 C13 116.4(4) . . ?
C3 C4 O3 124.4(5) . . ?
C3 C4 C9 120.9(4) . . ?
O3 C4 C9 114.7(4) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 O3 C15 119.3(4) . . ?
C15 C20 C19 119.4(4) . . ?
C15 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C20 C15 C16 122.3(5) . . ?
C20 C15 O3 120.5(4) . . ?
C16 C15 O3 117.0(4) . . ?
C20 C19 C18 118.3(4) . . ?
C20 C19 H19 120.8 . . ?
C18 C19 H19 120.8 . . ?
C16 C17 C18 118.8(5) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
C17 C16 C15 119.1(5) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C17 C18 C19 122.1(5) . . ?
C17 C18 Br1 119.4(3) . . ?
C19 C18 Br1 118.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.25
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.706
_refine_diff_density_rms         0.128
_database_code_depnum_ccdc_archive 'CCDC 961305'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_4

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H14 N2 O5'
_chemical_formula_sum            'C20 H14 N2 O5'
_chemical_formula_weight         362.33

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   13.916(5)
_cell_length_b                   11.329(4)
_cell_length_c                   10.530(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.067(7)
_cell_angle_gamma                90.00
_cell_volume                     1643.6(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3924
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      28.4

_exptl_crystal_description       rectangular
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18121
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_sigmaI/netI    0.0519
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         28.42
_reflns_number_total             3924
_reflns_number_gt                2384
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1999)'
_computing_publication_material  WinGX

_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 > 2σ(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)+(0.0539P)²+0.2164P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3924
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1100
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1397
_refine_ls_wR_factor_gt          0.1161
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.74251(10) 0.71188(13) 0.02138(16) 0.0494(4) Uani 1 1 d . . .
N1 N 0.30328(12) 0.63965(16) 0.11283(17) 0.0411(5) Uani 1 1 d . . .
C9 C 0.60559(14) 0.63281(17) 0.09513(18) 0.0327(5) Uani 1 1 d . . .
C8 C 0.46180(14) 0.54406(17) 0.16504(18) 0.0329(5) Uani 1 1 d . . .
O2 O 0.31689(12) 0.46926(15) 0.22742(17) 0.0593(5) Uani 1 1 d . . .
C1 C 0.44577(14) 0.72404(17) 0.03504(19) 0.0335(5) Uani 1 1 d . . .
C10 C 0.50382(14) 0.63464(17) 0.09858(18) 0.0306(4) Uani 1 1 d . . .
C5 C 0.66148(17) 0.54140(19) 0.1589(2) 0.0389(5) Uani 1 1 d . . .
O1 O 0.28766(11) 0.80050(14) -0.01644(17) 0.0566(5) Uani 1 1 d . . .
C4 C 0.64480(14) 0.72299(18) 0.0242(2) 0.0370(5) Uani 1 1 d . . .
C12 C 0.35632(16) 0.54563(19) 0.1717(2) 0.0394(5) Uani 1 1 d . . .
C11 C 0.34100(15) 0.72619(19) 0.0394(2) 0.0391(5) Uani 1 1 d . . .
C6 C 0.61844(17) 0.4549(2) 0.2213(2) 0.0436(6) Uani 1 1 d . . .
C7 C 0.51807(16) 0.4557(2) 0.2243(2) 0.0400(5) Uani 1 1 d . . .
C3 C 0.58740(16) 0.8087(2) -0.0393(2) 0.0432(6) Uani 1 1 d . . .
C15 C 0.79409(14) 0.79864(19) -0.0340(2) 0.0397(5) Uani 1 1 d . . .
N2 N 0.97072(13) 1.0416(2) -0.1902(2) 0.0497(5) Uani 1 1 d . . .
O5 O 1.02604(12) 1.00584(18) -0.26156(18) 0.0709(6) Uani 1 1 d . . .
C19 C 0.85448(15) 0.9936(2) -0.0433(2) 0.0402(5) Uani 1 1 d . . .
C2 C 0.48787(16) 0.80869(19) -0.0321(2) 0.0393(5) Uani 1 1 d . . .
C18 C 0.90837(14) 0.95612(19) -0.1359(2) 0.0383(5) Uani 1 1 d . . .
O4 O 0.96555(13) 1.14489(17) -0.1597(2) 0.0731(6) Uani 1 1 d . . .
C13 C 0.19822(17) 0.6474(3) 0.1241(3) 0.0536(7) Uani 1 1 d . . .
C20 C 0.79682(15) 0.9133(2) 0.0093(2) 0.0422(5) Uani 1 1 d . . .
C17 C 0.90636(17) 0.8411(2) -0.1785(2) 0.0477(6) Uani 1 1 d . . .
C16 C 0.84785(17) 0.7616(2) -0.1269(2) 0.0479(6) Uani 1 1 d . . .
C14 C 0.1355(2) 0.5979(3) 0.0093(3) 0.0697(9) Uani 1 1 d . . .
H2 H 0.4470(15) 0.8674(19) -0.076(2) 0.046(6) Uiso 1 1 d . . .
H20 H 0.7609(15) 0.9383(17) 0.073(2) 0.041(6) Uiso 1 1 d . . .
H3 H 0.6159(15) 0.8667(19) -0.088(2) 0.049(6) Uiso 1 1 d . . .
H14C H 0.150(2) 0.508(3) -0.002(3) 0.104(12) Uiso 1 1 d . . .
H7 H 0.4892(15) 0.393(2) 0.269(2) 0.049(6) Uiso 1 1 d . . .
H13A H 0.1939(17) 0.605(2) 0.206(2) 0.062(7) Uiso 1 1 d . . .
H6 H 0.6588(15) 0.394(2) 0.262(2) 0.047(6) Uiso 1 1 d . . .
H17 H 0.9443(16) 0.8178(19) -0.239(2) 0.054(7) Uiso 1 1 d . . .
H16 H 0.8434(16) 0.686(2) -0.156(2) 0.059(7) Uiso 1 1 d . . .
H19 H 0.8555(15) 1.072(2) -0.015(2) 0.055(7) Uiso 1 1 d . . .
H5 H 0.7288(16) 0.5420(18) 0.156(2) 0.048(7) Uiso 1 1 d . . .
H14B H 0.1479(19) 0.642(2) -0.074(3) 0.080(9) Uiso 1 1 d . . .
H13B H 0.1830(19) 0.736(3) 0.139(3) 0.084(9) Uiso 1 1 d . . .
H14A H 0.070(2) 0.611(3) 0.020(3) 0.098(10) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O3 C4 1.370(2) . ?
O3 C15 1.392(2) . ?
N1 C12 1.391(3) . ?
N1 C11 1.396(3) . ?
N1 C13 1.486(3) . ?
C9 C5 1.408(3) . ?
C9 C4 1.419(3) . ?
C9 C10 1.422(3) . ?
C8 C7 1.367(3) . ?
C8 C10 1.414(3) . ?
C8 C12 1.480(3) . ?
O2 C12 1.218(2) . ?
C1 C2 1.371(3) . ?
C1 C10 1.405(3) . ?
C1 C11 1.465(3) . ?
C5 C6 1.364(3) . ?
O1 C11 1.218(2) . ?
C4 C3 1.370(3) . ?
C6 C7 1.402(3) . ?
C3 C2 1.398(3) . ?
C15 C20 1.375(3) . ?
C15 C16 1.378(3) . ?
N2 O5 1.218(2) . ?
N2 O4 1.218(2) . ?
N2 C18 1.469(3) . ?
C19 C18 1.378(3) . ?
C19 C20 1.379(3) . ?
C18 C17 1.377(3) . ?
C13 C14 1.497(4) . ?
C17 C16 1.376(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
C4 O3 C15 121.04(16) . . ?
C12 N1 C11 124.58(18) . . ?
C12 N1 C13 118.44(19) . . ?
C11 N1 C13 116.95(19) . . ?
C5 C9 C4 123.58(19) . . ?
C5 C9 C10 118.96(18) . . ?
C4 C9 C10 117.44(18) . . ?
C7 C8 C10 120.49(19) . . ?
C7 C8 C12 119.72(19) . . ?
C10 C8 C12 119.78(18) . . ?
C2 C1 C10 119.41(19) . . ?
C2 C1 C11 120.24(19) . . ?
C10 C1 C11 120.35(18) . . ?
C1 C10 C8 120.57(18) . . ?
C1 C10 C9 120.43(17) . . ?
C8 C10 C9 118.99(18) . . ?
C6 C5 C9 120.5(2) . . ?
C3 C4 O3 124.57(19) . . ?
C3 C4 C9 121.72(19) . . ?
O3 C4 C9 113.65(18) . . ?
O2 C12 N1 120.8(2) . . ?
O2 C12 C8 122.1(2) . . ?
N1 C12 C8 117.12(18) . . ?
O1 C11 N1 120.12(19) . . ?
O1 C11 C1 122.6(2) . . ?
N1 C11 C1 117.30(19) . . ?
C5 C6 C7 120.9(2) . . ?
C8 C7 C6 120.2(2) . . ?
C4 C3 C2 119.3(2) . . ?
C20 C15 C16 122.0(2) . . ?
C20 C15 O3 121.3(2) . . ?
C16 C15 O3 116.4(2) . . ?
O5 N2 O4 123.2(2) . . ?
O5 N2 C18 118.7(2) . . ?
O4 N2 C18 118.1(2) . . ?
C18 C19 C20 119.1(2) . . ?
C1 C2 C3 121.7(2) . . ?
C17 C18 C19 122.3(2) . . ?
C17 C18 N2 118.9(2) . . ?
C19 C18 N2 118.9(2) . . ?
N1 C13 C14 112.5(2) . . ?
C15 C20 C19 118.7(2) . . ?
C16 C17 C18 118.5(2) . . ?
C17 C16 C15 119.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.951
_diffrn_reflns_theta_full        28.42
_diffrn_measured_fraction_theta_full 0.951
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.048
_database_code_depnum_ccdc_archive 'CCDC 961306'
