# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2014

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#                 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.
#
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#  fide research purposes only. It may contain copyright material
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data_d345

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 Br F N2 O4'
_chemical_formula_weight         383.18

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   5.6907(11)
_cell_length_b                   7.4227(14)
_cell_length_c                   9.3653(18)
_cell_angle_alpha                108.137(3)
_cell_angle_beta                 100.781(3)
_cell_angle_gamma                90.415(3)
_cell_volume                     368.39(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    871
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      27.47

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      'Not Measured'
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             192
_exptl_absorpt_coefficient_mu    2.823
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5831
_exptl_absorpt_correction_T_max  0.8372
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4816
_diffrn_reflns_av_R_equivalents  0.0145
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3338
_reflns_number_gt                3331
_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+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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.000(6)
_refine_ls_number_reflns         3338
_refine_ls_number_parameters     208
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.0947
_refine_ls_wR_factor_gt          0.0946
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.045
_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 1.1585 0.8390 1.2936 0.02136(10) Uani 1 1 d . . .
F1 F 0.4095(3) 0.3923(3) 0.5634(2) 0.0175(4) Uani 1 1 d . . .
O1 O 0.5131(5) 0.7334(4) 0.6030(3) 0.0262(5) Uani 1 1 d . . .
O2 O 0.8353(5) 0.6780(4) 0.5075(3) 0.0235(5) Uani 1 1 d . . .
O3 O 0.9475(5) 0.0212(4) 0.7936(3) 0.0227(5) Uani 1 1 d . . .
O4 O 1.1720(4) 0.0898(4) 0.6516(3) 0.0232(5) Uani 1 1 d . . .
N1 N 0.6571(5) 0.6292(4) 0.5454(4) 0.0159(5) Uani 1 1 d . . .
N2 N 0.9795(5) 0.0796(4) 0.6892(3) 0.0154(5) Uani 1 1 d . . .
C1 C 0.6169(5) 0.4129(4) 0.5135(4) 0.0132(5) Uani 1 1 d . . .
C2 C 0.8276(5) 0.3518(4) 0.6129(4) 0.0127(5) Uani 1 1 d . . .
H2A H 0.9714 0.3530 0.5660 0.015 Uiso 1 1 calc R . .
C3 C 0.7668(5) 0.1448(4) 0.6018(4) 0.0149(5) Uani 1 1 d . . .
H3A H 0.6237 0.1371 0.6462 0.018 Uiso 1 1 calc R . .
H3B H 0.7321 0.0632 0.4932 0.018 Uiso 1 1 calc R . .
C4 C 0.5776(5) 0.3205(4) 0.3424(4) 0.0130(5) Uani 1 1 d . . .
C5 C 0.7490(6) 0.2157(5) 0.2701(4) 0.0159(6) Uani 1 1 d . . .
H5 H 0.8982 0.2017 0.3296 0.019 Uiso 1 1 calc R . .
C6 C 0.7034(6) 0.1314(5) 0.1115(4) 0.0185(6) Uani 1 1 d . . .
H6 H 0.8203 0.0589 0.0633 0.022 Uiso 1 1 calc R . .
C7 C 0.4857(6) 0.1537(5) 0.0238(4) 0.0184(6) Uani 1 1 d . . .
H7 H 0.4525 0.0947 -0.0843 0.022 Uiso 1 1 calc R . .
C8 C 0.3170(6) 0.2630(5) 0.0954(4) 0.0200(6) Uani 1 1 d . . .
H8 H 0.1708 0.2814 0.0353 0.024 Uiso 1 1 calc R . .
C9 C 0.3599(6) 0.3448(5) 0.2527(4) 0.0173(6) Uani 1 1 d . . .
H9 H 0.2427 0.4175 0.3003 0.021 Uiso 1 1 calc R . .
C10 C 0.8918(5) 0.4816(4) 0.7783(4) 0.0127(5) Uani 1 1 d . . .
C11 C 0.7527(5) 0.4802(5) 0.8869(4) 0.0161(6) Uani 1 1 d . . .
H11 H 0.6057 0.4042 0.8557 0.019 Uiso 1 1 calc R . .
C12 C 0.8284(6) 0.5894(5) 1.0401(4) 0.0174(6) Uani 1 1 d . . .
H12 H 0.7345 0.5884 1.1138 0.021 Uiso 1 1 calc R . .
C13 C 1.0443(6) 0.6999(4) 1.0833(4) 0.0157(6) Uani 1 1 d . . .
C14 C 1.1817(6) 0.7066(5) 0.9777(4) 0.0176(6) Uani 1 1 d . . .
H14 H 1.3271 0.7846 1.0088 0.021 Uiso 1 1 calc R . .
C15 C 1.1034(6) 0.5972(5) 0.8254(4) 0.0157(6) Uani 1 1 d . . .
H15 H 1.1962 0.6015 0.7519 0.019 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.02985(16) 0.01777(14) 0.01256(14) 0.00136(9) 0.00066(9) 0.00180(9)
F1 0.0135(8) 0.0215(10) 0.0186(10) 0.0071(8) 0.0050(7) 0.0012(7)
O1 0.0266(12) 0.0185(12) 0.0305(14) 0.0040(11) 0.0047(11) 0.0075(10)
O2 0.0311(13) 0.0171(12) 0.0227(13) 0.0054(10) 0.0084(10) -0.0067(10)
O3 0.0329(12) 0.0218(12) 0.0135(11) 0.0086(10) -0.0005(9) -0.0013(9)
O4 0.0169(11) 0.0254(14) 0.0254(14) 0.0062(11) 0.0028(9) 0.0028(9)
N1 0.0210(13) 0.0121(13) 0.0134(14) 0.0043(11) -0.0002(10) 0.0007(10)
N2 0.0204(12) 0.0106(12) 0.0121(12) 0.0024(10) -0.0024(10) 0.0006(9)
C1 0.0131(12) 0.0134(14) 0.0138(14) 0.0050(11) 0.0033(10) 0.0004(10)
C2 0.0130(12) 0.0122(13) 0.0128(14) 0.0051(11) 0.0006(10) -0.0003(10)
C3 0.0160(13) 0.0122(13) 0.0151(14) 0.0052(11) -0.0013(11) -0.0011(10)
C4 0.0130(12) 0.0123(13) 0.0136(14) 0.0052(11) 0.0003(11) -0.0006(10)
C5 0.0145(12) 0.0172(14) 0.0147(15) 0.0041(12) 0.0020(11) 0.0013(11)
C6 0.0211(15) 0.0173(16) 0.0173(17) 0.0053(14) 0.0045(12) 0.0007(12)
C7 0.0245(15) 0.0162(14) 0.0118(14) 0.0034(12) -0.0006(12) -0.0046(12)
C8 0.0194(14) 0.0196(15) 0.0189(16) 0.0077(13) -0.0040(12) -0.0014(12)
C9 0.0151(13) 0.0148(14) 0.0196(16) 0.0051(12) -0.0016(11) 0.0009(11)
C10 0.0147(12) 0.0099(13) 0.0127(14) 0.0040(11) -0.0001(11) 0.0008(10)
C11 0.0150(12) 0.0165(14) 0.0166(15) 0.0055(12) 0.0027(11) -0.0008(10)
C12 0.0186(14) 0.0196(15) 0.0156(15) 0.0074(12) 0.0045(11) 0.0023(11)
C13 0.0224(15) 0.0098(13) 0.0129(15) 0.0020(11) 0.0010(12) 0.0024(11)
C14 0.0184(14) 0.0184(17) 0.0130(15) 0.0029(13) 0.0000(11) -0.0013(12)
C15 0.0178(14) 0.0154(14) 0.0131(15) 0.0032(12) 0.0036(11) -0.0012(11)

_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 C13 1.901(3) . ?
F1 C1 1.372(3) . ?
O1 N1 1.214(4) . ?
O2 N1 1.223(4) . ?
O3 N2 1.228(4) . ?
O4 N2 1.221(4) . ?
N1 C1 1.546(4) . ?
N2 C3 1.501(4) . ?
C1 C4 1.506(4) . ?
C1 C2 1.537(4) . ?
C2 C10 1.522(4) . ?
C2 C3 1.540(4) . ?
C2 H2A 1.0000 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.395(4) . ?
C4 C9 1.407(4) . ?
C5 C6 1.392(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.394(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.380(5) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C15 1.390(4) . ?
C10 C11 1.403(4) . ?
C11 C12 1.393(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(4) . ?
C14 C15 1.389(5) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?

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 N1 O2 126.2(3) . . ?
O1 N1 C1 118.8(3) . . ?
O2 N1 C1 114.9(3) . . ?
O4 N2 O3 124.9(3) . . ?
O4 N2 C3 117.4(3) . . ?
O3 N2 C3 117.7(3) . . ?
F1 C1 C4 109.7(2) . . ?
F1 C1 C2 109.4(2) . . ?
C4 C1 C2 117.6(3) . . ?
F1 C1 N1 104.6(2) . . ?
C4 C1 N1 107.0(2) . . ?
C2 C1 N1 107.6(2) . . ?
C10 C2 C1 114.4(2) . . ?
C10 C2 C3 112.1(2) . . ?
C1 C2 C3 107.5(2) . . ?
C10 C2 H2A 107.5 . . ?
C1 C2 H2A 107.5 . . ?
C3 C2 H2A 107.5 . . ?
N2 C3 C2 107.8(2) . . ?
N2 C3 H3A 110.2 . . ?
C2 C3 H3A 110.2 . . ?
N2 C3 H3B 110.2 . . ?
C2 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
C5 C4 C9 119.2(3) . . ?
C5 C4 C1 122.7(3) . . ?
C9 C4 C1 118.1(3) . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 119.6(3) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C9 C8 C7 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C4 120.0(3) . . ?
C8 C9 H9 120.0 . . ?
C4 C9 H9 120.0 . . ?
C15 C10 C11 118.9(3) . . ?
C15 C10 C2 118.6(3) . . ?
C11 C10 C2 122.3(3) . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 118.8(3) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C14 C13 C12 121.7(3) . . ?
C14 C13 Br1 119.0(2) . . ?
C12 C13 Br1 119.3(2) . . ?
C13 C14 C15 118.8(3) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C14 C15 C10 121.2(3) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.064
_database_code_depnum_ccdc_archive 'CCDC 975748'
