# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
_publ_author_address
M.Muller
; Institut f\"ur Organische Chemie
RWTH Aachen University
Landoltweg 1
52074 Aachen
Germany
;
M.Albrecht
; Institut f\"ur Organische Chemie
RWTH Aachen University
Landoltweg 1
52074 Aachen
Germany
;
C.Bannwarth
; Institut f\"ur Organische Chemie
RWTH Aachen University
Landoltweg 1
52074 Aachen
Germany
;
G.Raabe
; Institut f\"ur Organische Chemie
RWTH Aachen University
Landoltweg 1
52074 Aachen
Germany
;
A.Valkonen
; Department of Chemistry
Nanoscience Center
P.O. Box 35
FIN-00014 University of Jyv\"askyl\"a
Finland
;
K.Rissanen
; Department of Chemistry
Nanoscience Center
P.O. Box 35
FIN-00014 University of Jyv\"askyl\"a
Finland
;

_publ_contact_author_name        'Arto Valkonen'

_publ_contact_author_address     
;
Department of Chemistry
Nanoscience Center
P.O. Box 35
Survontie 9
FIN-00014 University of Jyv\"askyl\"a
Finland
;
_publ_contact_author_phone       '+358 14 260 2670'
_publ_contact_author_fax         '+358 14 260 2501'
_publ_contact_author_email       arto.m.valkonen@jyu.fi
_publ_requested_coeditor_name    ?

_publ_section_title              
;
From attraction to repulsion:
Anion- interactions between bromide and
fluorinated phenyl groups
;

data_2b
_database_code_depnum_ccdc_archive 'CCDC 817432'
#TrackingRef '- 2b_mm-179.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H15 F4 N2, Br'
_chemical_formula_sum            'C13 H15 Br F4 N2'
_chemical_formula_weight         355.18

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'
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           monoclinic
_symmetry_space_group_name_H-M   Cc

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'

_cell_length_a                   10.8019(3)
_cell_length_b                   10.6151(3)
_cell_length_c                   12.6264(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.992(2)
_cell_angle_gamma                90.00
_cell_volume                     1351.70(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    1722
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    3.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5507
_exptl_absorpt_correction_T_max  0.8368
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(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  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8159
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_sigmaI/netI    0.0572
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2237
_reflns_number_gt                2104
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, <i>et al.</i>, 2008);
POV-RAY (Cason, 2004)
;
_computing_publication_material  SHELXL-97

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0000P)^2^+1.0445P] where P=(Fo^2^+2Fc^2^)/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   0.098(11)
_refine_ls_number_reflns         2237
_refine_ls_number_parameters     182
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0661
_refine_ls_wR_factor_gt          0.0647
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.077
_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 0.40736(4) 0.34057(3) 0.17479(4) 0.02410(12) Uani 1 1 d . . .
F9 F 0.1887(3) 0.4028(3) 0.3646(3) 0.0308(7) Uani 1 1 d . . .
F10 F 0.0043(2) 0.4923(2) 0.4392(3) 0.0397(7) Uani 1 1 d . . .
F12 F 0.2455(3) 0.3296(3) 0.8040(3) 0.0434(10) Uani 1 1 d . . .
F13 F 0.4296(2) 0.2421(2) 0.7283(2) 0.0322(6) Uani 1 1 d . . .
N1 N 0.5336(4) 0.3641(3) 0.5146(3) 0.0173(9) Uani 1 1 d . . .
N2 N 0.7276(3) 0.5138(3) 0.5291(3) 0.0216(8) Uani 1 1 d . . .
C1 C 0.4812(4) 0.4866(4) 0.4530(3) 0.0195(9) Uani 1 1 d . . .
H1A H 0.4157 0.5244 0.4819 0.023 Uiso 1 1 calc R . .
H1B H 0.4370 0.4707 0.3707 0.023 Uiso 1 1 calc R . .
C2 C 0.5986(5) 0.5761(5) 0.4737(5) 0.0250(12) Uani 1 1 d . . .
H2A H 0.5953 0.6115 0.4002 0.030 Uiso 1 1 calc R . .
H2B H 0.5905 0.6469 0.5219 0.030 Uiso 1 1 calc R . .
C3 C 0.7349(4) 0.4740(4) 0.6434(3) 0.0226(9) Uani 1 1 d . . .
H3A H 0.7384 0.5494 0.6905 0.027 Uiso 1 1 calc R . .
H3B H 0.8172 0.4250 0.6801 0.027 Uiso 1 1 calc R . .
C4 C 0.6122(4) 0.3916(5) 0.6371(4) 0.0195(10) Uani 1 1 d . . .
H4A H 0.6422 0.3118 0.6791 0.023 Uiso 1 1 calc R . .
H4B H 0.5565 0.4373 0.6719 0.023 Uiso 1 1 calc R . .
C5 C 0.6260(4) 0.3040(4) 0.4634(3) 0.0204(9) Uani 1 1 d . . .
H5A H 0.5753 0.2761 0.3849 0.024 Uiso 1 1 calc R . .
H5B H 0.6694 0.2293 0.5085 0.024 Uiso 1 1 calc R . .
C6 C 0.7308(4) 0.4010(4) 0.4631(4) 0.0238(9) Uani 1 1 d . . .
H6A H 0.8197 0.3619 0.4949 0.029 Uiso 1 1 calc R . .
H6B H 0.7157 0.4259 0.3838 0.029 Uiso 1 1 calc R . .
C7 C 0.4200(4) 0.2744(4) 0.5014(3) 0.0196(9) Uani 1 1 d . . .
H7A H 0.3763 0.2538 0.4200 0.023 Uiso 1 1 calc R . .
H7B H 0.4567 0.1951 0.5418 0.023 Uiso 1 1 calc R . .
C8 C 0.3178(4) 0.3236(4) 0.5451(3) 0.0195(9) Uani 1 1 d . . .
C9 C 0.2057(4) 0.3855(4) 0.4741(4) 0.0235(9) Uani 1 1 d . . .
C10 C 0.1104(4) 0.4307(4) 0.5130(4) 0.0283(10) Uani 1 1 d . . .
C11 C 0.1200(5) 0.4126(4) 0.6236(4) 0.0328(11) Uani 1 1 d . . .
H11 H 0.0533 0.4426 0.6499 0.039 Uiso 1 1 calc R . .
C12 C 0.2298(6) 0.3493(5) 0.6948(5) 0.0322(13) Uani 1 1 d . . .
C13 C 0.3264(4) 0.3057(4) 0.6565(4) 0.0233(10) Uani 1 1 d . . .

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 0.0262(2) 0.02390(19) 0.01968(18) -0.0015(3) 0.00514(13) -0.0020(3)
F9 0.0234(14) 0.0357(17) 0.0303(16) 0.0073(14) 0.0059(12) -0.0023(13)
F10 0.0227(13) 0.0300(15) 0.0667(18) 0.0013(13) 0.0164(13) 0.0043(11)
F12 0.052(2) 0.052(2) 0.037(2) -0.0113(15) 0.0282(18) -0.0240(16)
F13 0.0337(15) 0.0338(15) 0.0263(12) 0.0059(11) 0.0075(12) -0.0086(12)
N1 0.019(2) 0.0172(19) 0.018(2) -0.0014(16) 0.0090(17) -0.0005(15)
N2 0.0193(17) 0.0249(19) 0.0207(18) -0.0005(15) 0.0071(15) -0.0006(15)
C1 0.020(2) 0.019(2) 0.0188(19) 0.0002(17) 0.0060(17) 0.0028(17)
C2 0.027(3) 0.024(3) 0.032(3) 0.007(2) 0.019(2) 0.003(2)
C3 0.023(2) 0.024(2) 0.024(2) -0.0023(18) 0.0112(18) -0.0084(18)
C4 0.017(2) 0.023(3) 0.017(2) -0.0006(19) 0.0033(18) 0.0011(19)
C5 0.019(2) 0.019(2) 0.023(2) -0.0028(17) 0.0078(18) 0.0056(17)
C6 0.021(2) 0.031(2) 0.020(2) -0.0001(18) 0.0085(18) 0.0019(19)
C7 0.016(2) 0.018(2) 0.023(2) -0.0083(17) 0.0055(17) -0.0049(16)
C8 0.017(2) 0.016(2) 0.028(2) -0.0042(17) 0.0109(18) -0.0052(17)
C9 0.024(2) 0.016(2) 0.033(2) 0.0016(18) 0.014(2) -0.0068(18)
C10 0.021(2) 0.020(2) 0.046(3) 0.002(2) 0.015(2) -0.0044(19)
C11 0.030(3) 0.026(3) 0.054(3) -0.014(2) 0.028(3) -0.007(2)
C12 0.038(3) 0.036(3) 0.030(3) -0.010(2) 0.020(2) -0.017(2)
C13 0.020(2) 0.024(2) 0.025(2) -0.0044(19) 0.007(2) -0.0069(18)

_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
F9 C9 1.340(5) . ?
F10 C10 1.358(5) . ?
F12 C12 1.344(6) . ?
F13 C13 1.340(5) . ?
N1 C4 1.502(6) . ?
N1 C5 1.512(6) . ?
N1 C7 1.514(5) . ?
N1 C1 1.517(5) . ?
N2 C6 1.467(6) . ?
N2 C2 1.472(6) . ?
N2 C3 1.478(5) . ?
C1 C2 1.531(7) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.566(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.532(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.494(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.387(6) . ?
C8 C13 1.390(6) . ?
C9 C10 1.376(6) . ?
C10 C11 1.376(7) . ?
C11 C12 1.379(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(7) . ?

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 N1 C5 107.8(3) . . ?
C4 N1 C7 111.9(4) . . ?
C5 N1 C7 108.6(3) . . ?
C4 N1 C1 109.4(3) . . ?
C5 N1 C1 109.0(3) . . ?
C7 N1 C1 110.1(3) . . ?
C6 N2 C2 107.9(3) . . ?
C6 N2 C3 108.5(3) . . ?
C2 N2 C3 107.6(3) . . ?
N1 C1 C2 108.1(3) . . ?
N1 C1 H1A 110.1 . . ?
C2 C1 H1A 110.1 . . ?
N1 C1 H1B 110.1 . . ?
C2 C1 H1B 110.1 . . ?
H1A C1 H1B 108.4 . . ?
N2 C2 C1 112.8(4) . . ?
N2 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
N2 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
N2 C3 C4 111.2(3) . . ?
N2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
N2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
N1 C4 C3 108.5(3) . . ?
N1 C4 H4A 110.0 . . ?
C3 C4 H4A 110.0 . . ?
N1 C4 H4B 110.0 . . ?
C3 C4 H4B 110.0 . . ?
H4A C4 H4B 108.4 . . ?
N1 C5 C6 108.6(3) . . ?
N1 C5 H5A 110.0 . . ?
C6 C5 H5A 110.0 . . ?
N1 C5 H5B 110.0 . . ?
C6 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
N2 C6 C5 112.3(3) . . ?
N2 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
N2 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 N1 114.6(3) . . ?
C8 C7 H7A 108.6 . . ?
N1 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
N1 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 C13 116.5(4) . . ?
C9 C8 C7 121.1(4) . . ?
C13 C8 C7 122.4(4) . . ?
F9 C9 C10 118.5(4) . . ?
F9 C9 C8 119.8(4) . . ?
C10 C9 C8 121.7(4) . . ?
F10 C10 C9 118.6(4) . . ?
F10 C10 C11 120.1(4) . . ?
C9 C10 C11 121.3(4) . . ?
C10 C11 C12 117.7(4) . . ?
C10 C11 H11 121.2 . . ?
C12 C11 H11 121.2 . . ?
F12 C12 C13 118.3(5) . . ?
F12 C12 C11 120.5(5) . . ?
C13 C12 C11 121.2(5) . . ?
F13 C13 C12 118.9(4) . . ?
F13 C13 C8 119.4(4) . . ?
C12 C13 C8 121.7(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 54.0(4) . . . . ?
C5 N1 C1 C2 -63.6(4) . . . . ?
C7 N1 C1 C2 177.3(4) . . . . ?
C6 N2 C2 C1 52.3(5) . . . . ?
C3 N2 C2 C1 -64.6(5) . . . . ?
N1 C1 C2 N2 9.5(5) . . . . ?
C6 N2 C3 C4 -62.5(4) . . . . ?
C2 N2 C3 C4 54.0(5) . . . . ?
C5 N1 C4 C3 55.2(5) . . . . ?
C7 N1 C4 C3 174.6(3) . . . . ?
C1 N1 C4 C3 -63.1(4) . . . . ?
N2 C3 C4 N1 7.5(5) . . . . ?
C4 N1 C5 C6 -65.7(4) . . . . ?
C7 N1 C5 C6 172.9(3) . . . . ?
C1 N1 C5 C6 52.9(4) . . . . ?
C2 N2 C6 C5 -63.9(4) . . . . ?
C3 N2 C6 C5 52.5(4) . . . . ?
N1 C5 C6 N2 10.2(5) . . . . ?
C4 N1 C7 C8 63.1(5) . . . . ?
C5 N1 C7 C8 -178.0(3) . . . . ?
C1 N1 C7 C8 -58.7(5) . . . . ?
N1 C7 C8 C9 93.2(5) . . . . ?
N1 C7 C8 C13 -89.6(5) . . . . ?
C13 C8 C9 F9 -178.0(3) . . . . ?
C7 C8 C9 F9 -0.6(6) . . . . ?
C13 C8 C9 C10 2.2(6) . . . . ?
C7 C8 C9 C10 179.6(4) . . . . ?
F9 C9 C10 F10 -0.9(6) . . . . ?
C8 C9 C10 F10 178.9(4) . . . . ?
F9 C9 C10 C11 178.0(4) . . . . ?
C8 C9 C10 C11 -2.2(7) . . . . ?
F10 C10 C11 C12 180.0(4) . . . . ?
C9 C10 C11 C12 1.1(6) . . . . ?
C10 C11 C12 F12 179.4(4) . . . . ?
C10 C11 C12 C13 -0.1(7) . . . . ?
F12 C12 C13 F13 2.1(6) . . . . ?
C11 C12 C13 F13 -178.4(4) . . . . ?
F12 C12 C13 C8 -179.3(4) . . . . ?
C11 C12 C13 C8 0.2(7) . . . . ?
C9 C8 C13 F13 177.3(3) . . . . ?
C7 C8 C13 F13 0.0(6) . . . . ?
C9 C8 C13 C12 -1.2(6) . . . . ?
C7 C8 C13 C12 -178.6(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.067

# Attachment '- 2c_mm-233-1.cif'

data_2c
_database_code_depnum_ccdc_archive 'CCDC 817433'
#TrackingRef '- 2c_mm-233-1.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H16 F3 N2, H2 O, Br'
_chemical_formula_sum            'C13 H18 Br F3 N2 O'
_chemical_formula_weight         355.20

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           monoclinic
_symmetry_space_group_name_H-M   P21

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.7372(2)
_cell_length_b                   15.5326(3)
_cell_length_c                   11.9888(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.314(2)
_cell_angle_gamma                90.00
_cell_volume                     1436.72(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3599
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    2.892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4981
_exptl_absorpt_correction_T_max  0.8456
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(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  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18276
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_sigmaI/netI    0.0554
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         25.02
_reflns_number_total             5022
_reflns_number_gt                4569
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, <i>et al.</i>, 2008);
POV-RAY (Cason, 2004)
;
_computing_publication_material  SHELXL-97

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0000P)^2^+0.4773P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.064(7)
_refine_ls_number_reflns         5022
_refine_ls_number_parameters     373
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0666
_refine_ls_wR_factor_gt          0.0641
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.090
_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 0.32973(5) 0.62703(2) 0.00930(3) 0.02903(11) Uani 1 1 d . . .
Br2 Br 0.08822(5) 0.94301(2) 0.43360(3) 0.03099(11) Uani 1 1 d . . .
F9 F 0.8615(3) 0.74143(13) 0.02626(17) 0.0273(5) Uani 1 1 d . . .
F11 F 0.8783(3) 0.47506(13) 0.2068(2) 0.0392(6) Uani 1 1 d . . .
F13 F 0.6669(3) 0.71594(14) 0.38609(17) 0.0272(5) Uani 1 1 d . . .
N1 N 0.5558(4) 0.85945(18) 0.1638(3) 0.0172(7) Uani 1 1 d . . .
N2 N 0.2645(4) 0.92131(18) 0.0833(3) 0.0218(7) Uani 1 1 d . . .
C1 C 0.5334(5) 0.8458(2) 0.0385(3) 0.0186(8) Uani 1 1 d . . .
H1A H 0.5187 0.7837 0.0216 0.022 Uiso 1 1 calc R . .
H1B H 0.6372 0.8666 0.0032 0.022 Uiso 1 1 calc R . .
C2 C 0.3731(5) 0.8956(3) -0.0074(3) 0.0252(9) Uani 1 1 d . . .
H2A H 0.4098 0.9477 -0.0469 0.030 Uiso 1 1 calc R . .
H2B H 0.3040 0.8593 -0.0620 0.030 Uiso 1 1 calc R . .
C3 C 0.2375(5) 0.8455(2) 0.1538(3) 0.0222(8) Uani 1 1 d . . .
H3A H 0.1884 0.7979 0.1066 0.027 Uiso 1 1 calc R . .
H3B H 0.1533 0.8600 0.2092 0.027 Uiso 1 1 calc R . .
C4 C 0.4085(5) 0.8162(2) 0.2152(3) 0.0193(8) Uani 1 1 d . . .
H4A H 0.4098 0.8315 0.2954 0.023 Uiso 1 1 calc R . .
H4B H 0.4201 0.7529 0.2093 0.023 Uiso 1 1 calc R . .
C5 C 0.5458(4) 0.9554(2) 0.1872(3) 0.0202(8) Uani 1 1 d . . .
H5A H 0.6293 0.9869 0.1437 0.024 Uiso 1 1 calc R . .
H5B H 0.5751 0.9667 0.2677 0.024 Uiso 1 1 calc R . .
C6 C 0.3598(5) 0.9858(2) 0.1534(4) 0.0256(9) Uani 1 1 d . . .
H6A H 0.2981 0.9963 0.2216 0.031 Uiso 1 1 calc R . .
H6B H 0.3639 1.0407 0.1118 0.031 Uiso 1 1 calc R . .
C7 C 0.7321(4) 0.8290(2) 0.2119(3) 0.0183(8) Uani 1 1 d . . .
H7A H 0.8225 0.8581 0.1715 0.022 Uiso 1 1 calc R . .
H7B H 0.7478 0.8469 0.2913 0.022 Uiso 1 1 calc R . .
C8 C 0.7590(4) 0.7339(2) 0.2055(3) 0.0183(8) Uani 1 1 d . . .
C9 C 0.8279(5) 0.6931(2) 0.1164(3) 0.0208(8) Uani 1 1 d . . .
C10 C 0.8672(5) 0.6068(2) 0.1121(3) 0.0251(9) Uani 1 1 d . . .
H10 H 0.9119 0.5814 0.0482 0.030 Uiso 1 1 calc R . .
C11 C 0.8380(5) 0.5593(2) 0.2059(3) 0.0243(9) Uani 1 1 d . . .
C12 C 0.7717(5) 0.5932(2) 0.2999(3) 0.0245(9) Uani 1 1 d . . .
H12 H 0.7537 0.5591 0.3638 0.029 Uiso 1 1 calc R . .
C13 C 0.7335(5) 0.6795(2) 0.2955(3) 0.0191(8) Uani 1 1 d . . .
F9A F 0.1512(3) 0.70281(14) 0.32924(18) 0.0271(5) Uani 1 1 d . . .
F11A F 0.4121(3) 0.43399(17) 0.2879(2) 0.0474(7) Uani 1 1 d . . .
F13A F 0.4940(3) 0.58126(14) 0.62757(18) 0.0289(5) Uani 1 1 d . . .
N1A N 0.1339(4) 0.71949(18) 0.6241(2) 0.0170(6) Uani 1 1 d . . .
N2A N -0.1284(4) 0.7218(2) 0.7426(3) 0.0224(7) Uani 1 1 d . . .
C1A C -0.0314(4) 0.7177(3) 0.5491(3) 0.0203(8) Uani 1 1 d U . .
H1C H -0.0406 0.6629 0.5070 0.024 Uiso 1 1 calc R . .
H1D H -0.0328 0.7658 0.4948 0.024 Uiso 1 1 calc R . .
C2A C -0.1838(5) 0.7266(4) 0.6238(3) 0.0396(11) Uani 1 1 d U . .
H2C H -0.2424 0.7824 0.6081 0.047 Uiso 1 1 calc R . .
H2D H -0.2689 0.6802 0.6050 0.047 Uiso 1 1 calc R . .
C3A C -0.0285(5) 0.6433(3) 0.7631(4) 0.0331(10) Uani 1 1 d U . .
H3C H -0.1013 0.5931 0.7395 0.040 Uiso 1 1 calc R . .
H3D H 0.0033 0.6378 0.8443 0.040 Uiso 1 1 calc R . .
C4A C 0.1374(4) 0.6419(2) 0.7001(3) 0.0191(8) Uani 1 1 d U . .
H4C H 0.2409 0.6439 0.7539 0.023 Uiso 1 1 calc R . .
H4D H 0.1424 0.5884 0.6556 0.023 Uiso 1 1 calc R . .
C5A C 0.1352(5) 0.8001(2) 0.6949(3) 0.0190(8) Uani 1 1 d U . .
H5C H 0.1228 0.8515 0.6462 0.023 Uiso 1 1 calc R . .
H5D H 0.2464 0.8046 0.7411 0.023 Uiso 1 1 calc R . .
C6A C -0.0168(6) 0.7958(3) 0.7713(4) 0.0368(11) Uani 1 1 d U . .
H6C H 0.0295 0.7912 0.8503 0.044 Uiso 1 1 calc R . .
H6D H -0.0858 0.8494 0.7630 0.044 Uiso 1 1 calc R . .
C7A C 0.2912(4) 0.7226(2) 0.5552(3) 0.0177(8) Uani 1 1 d . . .
H7C H 0.2814 0.7739 0.5062 0.021 Uiso 1 1 calc R . .
H7D H 0.3964 0.7298 0.6067 0.021 Uiso 1 1 calc R . .
C8A C 0.3145(4) 0.6440(2) 0.4835(3) 0.0186(8) Uani 1 1 d . . .
C9A C 0.2481(4) 0.6368(3) 0.3741(3) 0.0216(8) Uani 1 1 d . . .
C10A C 0.2763(5) 0.5673(3) 0.3049(3) 0.0272(9) Uani 1 1 d . . .
H10A H 0.2279 0.5646 0.2297 0.033 Uiso 1 1 calc R . .
C11A C 0.3784(5) 0.5026(3) 0.3520(4) 0.0339(10) Uani 1 1 d . . .
C12A C 0.4533(5) 0.5046(3) 0.4597(4) 0.0286(9) Uani 1 1 d . . .
H12A H 0.5253 0.4593 0.4893 0.034 Uiso 1 1 calc R . .
C13A C 0.4185(5) 0.5756(2) 0.5218(3) 0.0222(8) Uani 1 1 d . . .
O1 O -0.0982(4) 0.9452(2) 0.0244(3) 0.0486(9) Uani 1 1 d D . .
H1E H -0.139(7) 0.9953(19) 0.024(5) 0.073 Uiso 1 1 d D . .
H1F H 0.006(3) 0.958(4) 0.044(5) 0.073 Uiso 1 1 d D . .
O2 O -0.4788(3) 0.73583(19) 0.8076(2) 0.0310(7) Uani 1 1 d D . .
H2E H -0.502(6) 0.698(2) 0.853(3) 0.047 Uiso 1 1 d D . .
H2F H -0.371(3) 0.730(3) 0.809(4) 0.047 Uiso 1 1 d D . .

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 0.0367(2) 0.02371(19) 0.0280(2) -0.00640(17) 0.01086(16) -0.01086(19)
Br2 0.0404(2) 0.0257(2) 0.0266(2) 0.00598(17) 0.00029(17) 0.00057(19)
F9 0.0308(12) 0.0311(12) 0.0210(12) 0.0069(9) 0.0082(9) 0.0072(10)
F11 0.0497(15) 0.0167(11) 0.0496(17) 0.0025(10) -0.0064(12) 0.0055(11)
F13 0.0269(11) 0.0392(12) 0.0155(11) 0.0026(9) 0.0023(9) 0.0034(10)
N1 0.0145(15) 0.0148(15) 0.0227(17) -0.0018(13) 0.0028(13) -0.0010(13)
N2 0.0167(15) 0.0229(18) 0.0260(19) 0.0041(13) 0.0028(13) 0.0008(13)
C1 0.0183(18) 0.0255(19) 0.0119(19) -0.0044(15) 0.0008(14) -0.0051(16)
C2 0.022(2) 0.033(2) 0.021(2) 0.0018(17) 0.0009(16) 0.0024(17)
C3 0.0119(18) 0.0231(19) 0.032(2) 0.0036(17) 0.0031(16) 0.0011(16)
C4 0.0189(19) 0.0214(18) 0.018(2) 0.0018(15) 0.0028(15) -0.0015(16)
C5 0.0200(18) 0.0130(18) 0.028(2) -0.0060(15) 0.0017(15) -0.0004(16)
C6 0.022(2) 0.0165(18) 0.038(3) -0.0050(17) 0.0014(17) 0.0045(16)
C7 0.0128(17) 0.0228(19) 0.019(2) 0.0015(15) -0.0011(14) -0.0014(15)
C8 0.0112(17) 0.0191(18) 0.024(2) 0.0006(15) -0.0046(14) 0.0001(15)
C9 0.0177(18) 0.028(2) 0.017(2) -0.0003(16) 0.0027(15) 0.0023(16)
C10 0.0228(19) 0.027(2) 0.025(2) -0.0031(16) 0.0004(16) 0.0080(16)
C11 0.024(2) 0.0155(18) 0.033(2) 0.0008(17) -0.0051(18) 0.0021(16)
C12 0.021(2) 0.027(2) 0.025(2) 0.0077(17) -0.0035(16) -0.0036(17)
C13 0.0144(18) 0.030(2) 0.0127(19) 0.0014(16) -0.0011(14) -0.0011(16)
F9A 0.0242(11) 0.0362(13) 0.0207(12) 0.0054(10) 0.0002(9) 0.0042(10)
F11A 0.0519(16) 0.0392(15) 0.0527(16) -0.0211(14) 0.0147(13) 0.0033(14)
F13A 0.0284(12) 0.0316(12) 0.0263(13) 0.0089(10) 0.0001(10) 0.0020(10)
N1A 0.0184(15) 0.0199(14) 0.0129(16) 0.0017(12) 0.0020(12) -0.0062(13)
N2A 0.0214(16) 0.0279(17) 0.0181(17) -0.0011(13) 0.0025(13) -0.0054(14)
C1A 0.0135(17) 0.033(2) 0.0141(19) 0.0020(16) -0.0018(14) -0.0049(16)
C2A 0.016(2) 0.081(3) 0.022(2) -0.004(2) 0.0049(17) -0.006(2)
C3A 0.039(2) 0.027(2) 0.035(2) 0.0104(17) 0.0174(19) 0.0033(19)
C4A 0.0216(17) 0.020(2) 0.0158(18) 0.0031(14) 0.0039(14) -0.0056(15)
C5A 0.0203(18) 0.0162(18) 0.020(2) -0.0034(15) 0.0007(15) -0.0041(15)
C6A 0.038(2) 0.030(2) 0.045(3) -0.015(2) 0.018(2) -0.008(2)
C7A 0.0095(16) 0.0206(18) 0.023(2) 0.0045(15) 0.0037(14) -0.0057(15)
C8A 0.0159(17) 0.020(2) 0.021(2) 0.0036(15) 0.0071(15) -0.0043(15)
C9A 0.0151(17) 0.029(2) 0.021(2) 0.0046(17) 0.0039(14) -0.0031(18)
C10A 0.024(2) 0.038(2) 0.020(2) -0.0049(17) 0.0016(16) -0.0046(19)
C11A 0.027(2) 0.033(2) 0.043(3) -0.010(2) 0.014(2) -0.005(2)
C12A 0.025(2) 0.025(2) 0.037(3) 0.0058(18) 0.0087(18) 0.0030(18)
C13A 0.0175(19) 0.027(2) 0.022(2) 0.0069(16) 0.0016(16) -0.0011(17)
O1 0.0212(14) 0.0325(16) 0.092(3) 0.025(2) 0.0046(15) 0.0004(15)
O2 0.0180(14) 0.0443(19) 0.0308(17) 0.0026(13) 0.0015(13) 0.0004(14)

_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
F9 C9 1.357(4) . ?
F11 C11 1.344(4) . ?
F13 C13 1.359(4) . ?
N1 C4 1.496(5) . ?
N1 C1 1.514(5) . ?
N1 C7 1.516(4) . ?
N1 C5 1.519(4) . ?
N2 C6 1.470(5) . ?
N2 C3 1.474(5) . ?
N2 C2 1.477(5) . ?
C1 C2 1.529(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.534(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.540(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.495(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.382(5) . ?
C8 C13 1.396(5) . ?
C9 C10 1.376(5) . ?
C10 C11 1.378(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.378(6) . ?
C12 C13 1.373(5) . ?
C12 H12 0.9500 . ?
F9A C9A 1.357(4) . ?
F11A C11A 1.351(5) . ?
F13A C13A 1.358(5) . ?
N1A C1A 1.508(4) . ?
N1A C4A 1.511(4) . ?
N1A C5A 1.513(4) . ?
N1A C7A 1.522(4) . ?
N2A C3A 1.455(5) . ?
N2A C2A 1.458(5) . ?
N2A C6A 1.463(5) . ?
C1A C2A 1.540(5) . ?
C1A H1C 0.9900 . ?
C1A H1D 0.9900 . ?
C2A H2C 0.9900 . ?
C2A H2D 0.9900 . ?
C3A C4A 1.537(5) . ?
C3A H3C 0.9900 . ?
C3A H3D 0.9900 . ?
C4A H4C 0.9900 . ?
C4A H4D 0.9900 . ?
C5A C6A 1.545(5) . ?
C5A H5C 0.9900 . ?
C5A H5D 0.9900 . ?
C6A H6C 0.9900 . ?
C6A H6D 0.9900 . ?
C7A C8A 1.511(5) . ?
C7A H7C 0.9900 . ?
C7A H7D 0.9900 . ?
C8A C9A 1.376(5) . ?
C8A C13A 1.390(5) . ?
C9A C10A 1.390(6) . ?
C10A C11A 1.373(6) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.375(6) . ?
C12A C13A 1.369(6) . ?
C12A H12A 0.9500 . ?
O1 H1E 0.84(2) . ?
O1 H1F 0.85(2) . ?
O2 H2E 0.828(19) . ?
O2 H2F 0.835(19) . ?

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 N1 C1 108.2(3) . . ?
C4 N1 C7 113.3(3) . . ?
C1 N1 C7 111.5(3) . . ?
C4 N1 C5 108.3(3) . . ?
C1 N1 C5 108.5(3) . . ?
C7 N1 C5 107.0(3) . . ?
C6 N2 C3 107.6(3) . . ?
C6 N2 C2 108.4(3) . . ?
C3 N2 C2 108.7(3) . . ?
N1 C1 C2 108.3(3) . . ?
N1 C1 H1A 110.0 . . ?
C2 C1 H1A 110.0 . . ?
N1 C1 H1B 110.0 . . ?
C2 C1 H1B 110.0 . . ?
H1A C1 H1B 108.4 . . ?
N2 C2 C1 111.3(3) . . ?
N2 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
N2 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N2 C3 C4 111.0(3) . . ?
N2 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
N2 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
N1 C4 C3 109.0(3) . . ?
N1 C4 H4A 109.9 . . ?
C3 C4 H4A 109.9 . . ?
N1 C4 H4B 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
N1 C5 C6 108.2(3) . . ?
N1 C5 H5A 110.1 . . ?
C6 C5 H5A 110.1 . . ?
N1 C5 H5B 110.1 . . ?
C6 C5 H5B 110.1 . . ?
H5A C5 H5B 108.4 . . ?
N2 C6 C5 111.1(3) . . ?
N2 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
N2 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 N1 114.4(3) . . ?
C8 C7 H7A 108.7 . . ?
N1 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
N1 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 C13 113.9(3) . . ?
C9 C8 C7 123.8(3) . . ?
C13 C8 C7 121.9(3) . . ?
F9 C9 C10 116.9(3) . . ?
F9 C9 C8 118.0(3) . . ?
C10 C9 C8 125.0(4) . . ?
C9 C10 C11 116.2(4) . . ?
C9 C10 H10 121.9 . . ?
C11 C10 H10 121.9 . . ?
F11 C11 C10 118.4(3) . . ?
F11 C11 C12 117.8(4) . . ?
C10 C11 C12 123.8(3) . . ?
C13 C12 C11 115.8(4) . . ?
C13 C12 H12 122.1 . . ?
C11 C12 H12 122.1 . . ?
F13 C13 C12 118.0(3) . . ?
F13 C13 C8 116.8(3) . . ?
C12 C13 C8 125.2(4) . . ?
C1A N1A C4A 108.7(3) . . ?
C1A N1A C5A 108.6(3) . . ?
C4A N1A C5A 108.8(3) . . ?
C1A N1A C7A 110.8(3) . . ?
C4A N1A C7A 111.9(3) . . ?
C5A N1A C7A 107.9(3) . . ?
C3A N2A C2A 108.7(3) . . ?
C3A N2A C6A 108.8(3) . . ?
C2A N2A C6A 108.3(3) . . ?
N1A C1A C2A 107.7(3) . . ?
N1A C1A H1C 110.2 . . ?
C2A C1A H1C 110.2 . . ?
N1A C1A H1D 110.2 . . ?
C2A C1A H1D 110.2 . . ?
H1C C1A H1D 108.5 . . ?
N2A C2A C1A 112.5(3) . . ?
N2A C2A H2C 109.1 . . ?
C1A C2A H2C 109.1 . . ?
N2A C2A H2D 109.1 . . ?
C1A C2A H2D 109.1 . . ?
H2C C2A H2D 107.8 . . ?
N2A C3A C4A 112.5(3) . . ?
N2A C3A H3C 109.1 . . ?
C4A C3A H3C 109.1 . . ?
N2A C3A H3D 109.1 . . ?
C4A C3A H3D 109.1 . . ?
H3C C3A H3D 107.8 . . ?
N1A C4A C3A 107.9(3) . . ?
N1A C4A H4C 110.1 . . ?
C3A C4A H4C 110.1 . . ?
N1A C4A H4D 110.1 . . ?
C3A C4A H4D 110.1 . . ?
H4C C4A H4D 108.4 . . ?
N1A C5A C6A 108.9(3) . . ?
N1A C5A H5C 109.9 . . ?
C6A C5A H5C 109.9 . . ?
N1A C5A H5D 109.9 . . ?
C6A C5A H5D 109.9 . . ?
H5C C5A H5D 108.3 . . ?
N2A C6A C5A 110.9(3) . . ?
N2A C6A H6C 109.5 . . ?
C5A C6A H6C 109.5 . . ?
N2A C6A H6D 109.5 . . ?
C5A C6A H6D 109.5 . . ?
H6C C6A H6D 108.0 . . ?
C8A C7A N1A 114.7(3) . . ?
C8A C7A H7C 108.6 . . ?
N1A C7A H7C 108.6 . . ?
C8A C7A H7D 108.6 . . ?
N1A C7A H7D 108.6 . . ?
H7C C7A H7D 107.6 . . ?
C9A C8A C13A 114.7(3) . . ?
C9A C8A C7A 123.8(3) . . ?
C13A C8A C7A 121.3(3) . . ?
F9A C9A C8A 118.2(3) . . ?
F9A C9A C10A 117.2(3) . . ?
C8A C9A C10A 124.6(4) . . ?
C11A C10A C9A 115.7(4) . . ?
C11A C10A H10A 122.1 . . ?
C9A C10A H10A 122.1 . . ?
F11A C11A C10A 118.2(4) . . ?
F11A C11A C12A 117.8(4) . . ?
C10A C11A C12A 124.0(4) . . ?
C13A C12A C11A 116.3(4) . . ?
C13A C12A H12A 121.8 . . ?
C11A C12A H12A 121.8 . . ?
F13A C13A C12A 118.1(3) . . ?
F13A C13A C8A 117.2(3) . . ?
C12A C13A C8A 124.6(4) . . ?
H1E O1 H1F 97(5) . . ?
H2E O2 H2F 100(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 67.5(4) . . . . ?
C7 N1 C1 C2 -167.4(3) . . . . ?
C5 N1 C1 C2 -49.8(4) . . . . ?
C6 N2 C2 C1 67.8(4) . . . . ?
C3 N2 C2 C1 -48.9(4) . . . . ?
N1 C1 C2 N2 -15.3(4) . . . . ?
C6 N2 C3 C4 -51.2(4) . . . . ?
C2 N2 C3 C4 66.0(4) . . . . ?
C1 N1 C4 C3 -50.9(4) . . . . ?
C7 N1 C4 C3 -175.0(3) . . . . ?
C5 N1 C4 C3 66.5(4) . . . . ?
N2 C3 C4 N1 -13.8(4) . . . . ?
C4 N1 C5 C6 -50.2(4) . . . . ?
C1 N1 C5 C6 67.0(4) . . . . ?
C7 N1 C5 C6 -172.6(3) . . . . ?
C3 N2 C6 C5 67.9(4) . . . . ?
C2 N2 C6 C5 -49.5(4) . . . . ?
N1 C5 C6 N2 -15.0(4) . . . . ?
C4 N1 C7 C8 55.6(4) . . . . ?
C1 N1 C7 C8 -66.7(4) . . . . ?
C5 N1 C7 C8 174.8(3) . . . . ?
N1 C7 C8 C9 90.5(4) . . . . ?
N1 C7 C8 C13 -96.6(4) . . . . ?
C13 C8 C9 F9 -178.3(3) . . . . ?
C7 C8 C9 F9 -4.9(5) . . . . ?
C13 C8 C9 C10 1.0(5) . . . . ?
C7 C8 C9 C10 174.4(4) . . . . ?
F9 C9 C10 C11 177.8(3) . . . . ?
C8 C9 C10 C11 -1.5(6) . . . . ?
C9 C10 C11 F11 -178.4(3) . . . . ?
C9 C10 C11 C12 0.7(6) . . . . ?
F11 C11 C12 C13 179.6(3) . . . . ?
C10 C11 C12 C13 0.5(6) . . . . ?
C11 C12 C13 F13 179.6(3) . . . . ?
C11 C12 C13 C8 -1.0(6) . . . . ?
C9 C8 C13 F13 179.6(3) . . . . ?
C7 C8 C13 F13 6.1(5) . . . . ?
C9 C8 C13 C12 0.3(5) . . . . ?
C7 C8 C13 C12 -173.2(4) . . . . ?
C4A N1A C1A C2A 63.9(4) . . . . ?
C5A N1A C1A C2A -54.5(4) . . . . ?
C7A N1A C1A C2A -172.8(3) . . . . ?
C3A N2A C2A C1A -53.5(5) . . . . ?
C6A N2A C2A C1A 64.5(5) . . . . ?
N1A C1A C2A N2A -8.1(5) . . . . ?
C2A N2A C3A C4A 62.3(4) . . . . ?
C6A N2A C3A C4A -55.4(4) . . . . ?
C1A N1A C4A C3A -55.7(4) . . . . ?
C5A N1A C4A C3A 62.5(4) . . . . ?
C7A N1A C4A C3A -178.4(3) . . . . ?
N2A C3A C4A N1A -6.8(4) . . . . ?
C1A N1A C5A C6A 63.5(4) . . . . ?
C4A N1A C5A C6A -54.8(4) . . . . ?
C7A N1A C5A C6A -176.4(3) . . . . ?
C3A N2A C6A C5A 63.3(4) . . . . ?
C2A N2A C6A C5A -54.7(4) . . . . ?
N1A C5A C6A N2A -7.3(5) . . . . ?
C1A N1A C7A C8A -64.2(4) . . . . ?
C4A N1A C7A C8A 57.4(4) . . . . ?
C5A N1A C7A C8A 177.1(3) . . . . ?
N1A C7A C8A C9A 92.0(4) . . . . ?
N1A C7A C8A C13A -93.4(4) . . . . ?
C13A C8A C9A F9A -177.3(3) . . . . ?
C7A C8A C9A F9A -2.4(5) . . . . ?
C13A C8A C9A C10A 1.2(5) . . . . ?
C7A C8A C9A C10A 176.2(3) . . . . ?
F9A C9A C10A C11A 178.4(3) . . . . ?
C8A C9A C10A C11A -0.1(6) . . . . ?
C9A C10A C11A F11A -179.0(3) . . . . ?
C9A C10A C11A C12A -1.2(6) . . . . ?
F11A C11A C12A C13A 179.1(3) . . . . ?
C10A C11A C12A C13A 1.3(6) . . . . ?
C11A C12A C13A F13A -178.2(3) . . . . ?
C11A C12A C13A C8A 0.0(6) . . . . ?
C9A C8A C13A F13A 177.0(3) . . . . ?
C7A C8A C13A F13A 1.9(5) . . . . ?
C9A C8A C13A C12A -1.2(5) . . . . ?
C7A C8A C13A C12A -176.3(3) . . . . ?

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
O1 H1E Br1 0.84(2) 2.53(3) 3.353(3) 164(5) 2
O1 H1F N2 0.85(2) 2.10(3) 2.866(4) 150(5) .
O2 H2E Br1 0.828(19) 2.61(3) 3.382(3) 157(4) 1_456
O2 H2F N2A 0.835(19) 2.10(3) 2.885(4) 156(5) .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.062

# Attachment '- 2d_mm-aa-79-5.cif'

data_2d
_database_code_depnum_ccdc_archive 'CCDC 817434'
#TrackingRef '- 2d_mm-aa-79-5.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H17 F2 N2, H2 O, Br'
_chemical_formula_sum            'C13 H19 Br F2 N2 O'
_chemical_formula_weight         337.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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   P21/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.97390(10)
_cell_length_b                   10.8494(2)
_cell_length_c                   18.6609(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.3500(10)
_cell_angle_gamma                90.00
_cell_volume                     1410.75(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3592
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    2.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4540
_exptl_absorpt_correction_T_max  0.7784
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(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  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8298
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         25.24
_reflns_number_total             2555
_reflns_number_gt                2176
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, <i>et al.</i>, 2008);
POV-RAY (Cason, 2004)
;
_computing_publication_material  SHELXL-97

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0123P)^2^+1.3112P] where P=(Fo^2^+2Fc^2^)/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         2555
_refine_ls_number_parameters     178
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0600
_refine_ls_wR_factor_gt          0.0579
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.34357(4) 0.61922(2) 0.610364(15) 0.03599(10) Uani 1 1 d . . .
F9 F 0.89373(18) 0.59391(12) 0.95634(7) 0.0313(3) Uani 1 1 d . . .
F13 F 0.24621(18) 0.59911(12) 0.87846(7) 0.0303(3) Uani 1 1 d . . .
N1 N 0.6181(3) 0.81731(16) 0.86351(9) 0.0193(4) Uani 1 1 d . . .
N2 N 0.7007(3) 0.95916(18) 0.75866(10) 0.0288(5) Uani 1 1 d . . .
C1 C 0.6316(3) 0.9502(2) 0.88797(13) 0.0247(5) Uani 1 1 d . . .
H1A H 0.7417 0.9605 0.9227 0.030 Uiso 1 1 calc R . .
H1B H 0.5131 0.9740 0.9119 0.030 Uiso 1 1 calc R . .
C2 C 0.6585(4) 1.0326(2) 0.82215(13) 0.0270(5) Uani 1 1 d . . .
H2A H 0.5403 1.0813 0.8122 0.032 Uiso 1 1 calc R . .
H2B H 0.7652 1.0910 0.8325 0.032 Uiso 1 1 calc R . .
C3 C 0.5302(4) 0.8841(2) 0.73965(13) 0.0350(6) Uani 1 1 d . . .
H3A H 0.5598 0.8278 0.6998 0.042 Uiso 1 1 calc R . .
H3B H 0.4240 0.9388 0.7229 0.042 Uiso 1 1 calc R . .
C4 C 0.4660(3) 0.8079(2) 0.80402(12) 0.0275(5) Uani 1 1 d . . .
H4A H 0.3425 0.8398 0.8206 0.033 Uiso 1 1 calc R . .
H4B H 0.4478 0.7207 0.7897 0.033 Uiso 1 1 calc R . .
C5 C 0.8090(3) 0.7806(2) 0.83447(12) 0.0232(5) Uani 1 1 d . . .
H5A H 0.7998 0.6975 0.8126 0.028 Uiso 1 1 calc R . .
H5B H 0.9090 0.7786 0.8737 0.028 Uiso 1 1 calc R . .
C6 C 0.8615(4) 0.8766(2) 0.77746(12) 0.0289(5) Uani 1 1 d . . .
H6A H 0.9719 0.9262 0.7960 0.035 Uiso 1 1 calc R . .
H6B H 0.9009 0.8333 0.7338 0.035 Uiso 1 1 calc R . .
C7 C 0.5678(3) 0.7399(2) 0.92777(11) 0.0203(5) Uani 1 1 d . . .
H7A H 0.6585 0.7604 0.9682 0.024 Uiso 1 1 calc R . .
H7B H 0.4376 0.7633 0.9421 0.024 Uiso 1 1 calc R . .
C8 C 0.5720(3) 0.6030(2) 0.91616(11) 0.0195(5) Uani 1 1 d . . .
C9 C 0.7332(3) 0.5326(2) 0.93385(12) 0.0226(5) Uani 1 1 d . . .
C10 C 0.7380(3) 0.4059(2) 0.93154(12) 0.0256(5) Uani 1 1 d . . .
H10 H 0.8526 0.3618 0.9434 0.031 Uiso 1 1 calc R . .
C11 C 0.5698(4) 0.3447(2) 0.91128(12) 0.0271(5) Uani 1 1 d . . .
H11 H 0.5686 0.2572 0.9100 0.032 Uiso 1 1 calc R . .
C12 C 0.4035(3) 0.4091(2) 0.89291(12) 0.0254(5) Uani 1 1 d . . .
H12 H 0.2885 0.3670 0.8789 0.030 Uiso 1 1 calc R . .
C13 C 0.4097(3) 0.5357(2) 0.89549(11) 0.0218(5) Uani 1 1 d . . .
O14 O 0.3521(3) 0.35508(18) 0.52470(12) 0.0445(5) Uani 1 1 d D . .
H14A H 0.352(5) 0.426(2) 0.5422(18) 0.067 Uiso 1 1 d D . .
H14B H 0.428(4) 0.357(3) 0.4907(14) 0.067 Uiso 1 1 d D . .

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 0.02761(14) 0.02868(15) 0.05126(18) -0.00462(12) -0.00321(11) 0.00620(11)
F9 0.0227(7) 0.0309(8) 0.0396(8) 0.0073(6) -0.0079(6) -0.0020(6)
F13 0.0194(6) 0.0319(7) 0.0395(8) 0.0011(6) -0.0020(6) -0.0023(6)
N1 0.0205(9) 0.0196(10) 0.0178(9) -0.0009(8) -0.0007(8) -0.0017(8)
N2 0.0390(12) 0.0253(11) 0.0216(10) 0.0026(8) -0.0043(9) -0.0072(9)
C1 0.0306(13) 0.0175(11) 0.0258(12) -0.0052(10) 0.0001(10) -0.0005(10)
C2 0.0291(13) 0.0209(12) 0.0309(13) 0.0022(10) -0.0012(10) -0.0029(10)
C3 0.0481(16) 0.0326(14) 0.0231(12) 0.0060(11) -0.0127(11) -0.0130(12)
C4 0.0251(12) 0.0321(14) 0.0244(12) 0.0017(11) -0.0081(10) -0.0059(10)
C5 0.0223(11) 0.0252(12) 0.0223(12) -0.0018(10) 0.0043(10) 0.0013(10)
C6 0.0375(14) 0.0259(13) 0.0240(12) -0.0009(10) 0.0088(11) -0.0043(11)
C7 0.0211(11) 0.0223(12) 0.0175(11) 0.0009(9) 0.0009(9) -0.0023(9)
C8 0.0226(11) 0.0216(11) 0.0146(10) 0.0012(9) 0.0032(9) -0.0016(9)
C9 0.0230(12) 0.0272(12) 0.0177(11) 0.0025(10) 0.0012(9) -0.0031(10)
C10 0.0316(13) 0.0271(13) 0.0183(11) 0.0042(10) 0.0034(10) 0.0060(10)
C11 0.0439(15) 0.0217(12) 0.0160(11) 0.0002(9) 0.0047(11) -0.0014(11)
C12 0.0325(13) 0.0268(13) 0.0169(11) -0.0019(10) 0.0014(10) -0.0092(10)
C13 0.0215(11) 0.0277(12) 0.0164(11) 0.0006(9) 0.0032(9) 0.0006(10)
O14 0.0459(12) 0.0279(10) 0.0603(14) -0.0024(10) 0.0103(10) -0.0074(9)

_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
F9 C9 1.354(3) . ?
F13 C13 1.358(3) . ?
N1 C4 1.507(3) . ?
N1 C5 1.511(3) . ?
N1 C1 1.514(3) . ?
N1 C7 1.517(3) . ?
N2 C6 1.466(3) . ?
N2 C2 1.468(3) . ?
N2 C3 1.473(3) . ?
C1 C2 1.537(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.539(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.544(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.501(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.387(3) . ?
C8 C13 1.388(3) . ?
C9 C10 1.376(3) . ?
C10 C11 1.387(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.376(3) . ?
C12 H12 0.9500 . ?
O14 H14A 0.840(18) . ?
O14 H14B 0.844(18) . ?

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 N1 C5 108.77(17) . . ?
C4 N1 C1 108.64(17) . . ?
C5 N1 C1 108.33(17) . . ?
C4 N1 C7 111.47(16) . . ?
C5 N1 C7 111.92(16) . . ?
C1 N1 C7 107.61(16) . . ?
C6 N2 C2 108.37(18) . . ?
C6 N2 C3 108.77(19) . . ?
C2 N2 C3 108.0(2) . . ?
N1 C1 C2 108.74(18) . . ?
N1 C1 H1A 109.9 . . ?
C2 C1 H1A 109.9 . . ?
N1 C1 H1B 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
N2 C2 C1 111.35(19) . . ?
N2 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
N2 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N2 C3 C4 111.51(18) . . ?
N2 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
N2 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
N1 C4 C3 108.67(18) . . ?
N1 C4 H4A 110.0 . . ?
C3 C4 H4A 110.0 . . ?
N1 C4 H4B 110.0 . . ?
C3 C4 H4B 110.0 . . ?
H4A C4 H4B 108.3 . . ?
N1 C5 C6 107.81(18) . . ?
N1 C5 H5A 110.1 . . ?
C6 C5 H5A 110.1 . . ?
N1 C5 H5B 110.1 . . ?
C6 C5 H5B 110.1 . . ?
H5A C5 H5B 108.5 . . ?
N2 C6 C5 112.13(19) . . ?
N2 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
N2 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 N1 115.28(17) . . ?
C8 C7 H7A 108.5 . . ?
N1 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
N1 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C9 C8 C13 114.8(2) . . ?
C9 C8 C7 122.1(2) . . ?
C13 C8 C7 122.7(2) . . ?
F9 C9 C10 118.7(2) . . ?
F9 C9 C8 117.1(2) . . ?
C10 C9 C8 124.3(2) . . ?
C9 C10 C11 117.8(2) . . ?
C9 C10 H10 121.1 . . ?
C11 C10 H10 121.1 . . ?
C12 C11 C10 121.1(2) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C13 C12 C11 118.1(2) . . ?
C13 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?
F13 C13 C12 118.2(2) . . ?
F13 C13 C8 117.8(2) . . ?
C12 C13 C8 124.0(2) . . ?
H14A O14 H14B 106(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 -52.5(2) . . . . ?
C5 N1 C1 C2 65.5(2) . . . . ?
C7 N1 C1 C2 -173.28(17) . . . . ?
C6 N2 C2 C1 -52.0(2) . . . . ?
C3 N2 C2 C1 65.6(2) . . . . ?
N1 C1 C2 N2 -11.1(3) . . . . ?
C6 N2 C3 C4 63.8(3) . . . . ?
C2 N2 C3 C4 -53.6(3) . . . . ?
C5 N1 C4 C3 -53.8(2) . . . . ?
C1 N1 C4 C3 63.9(2) . . . . ?
C7 N1 C4 C3 -177.67(19) . . . . ?
N2 C3 C4 N1 -9.6(3) . . . . ?
C4 N1 C5 C6 65.0(2) . . . . ?
C1 N1 C5 C6 -52.9(2) . . . . ?
C7 N1 C5 C6 -171.40(17) . . . . ?
C2 N2 C6 C5 65.2(2) . . . . ?
C3 N2 C6 C5 -52.0(2) . . . . ?
N1 C5 C6 N2 -10.6(3) . . . . ?
C4 N1 C7 C8 68.2(2) . . . . ?
C5 N1 C7 C8 -53.8(2) . . . . ?
C1 N1 C7 C8 -172.74(18) . . . . ?
N1 C7 C8 C9 94.1(2) . . . . ?
N1 C7 C8 C13 -94.0(2) . . . . ?
C13 C8 C9 F9 -178.16(18) . . . . ?
C7 C8 C9 F9 -5.7(3) . . . . ?
C13 C8 C9 C10 0.2(3) . . . . ?
C7 C8 C9 C10 172.7(2) . . . . ?
F9 C9 C10 C11 177.31(19) . . . . ?
C8 C9 C10 C11 -1.1(3) . . . . ?
C9 C10 C11 C12 1.0(3) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?
C11 C12 C13 F13 -179.11(18) . . . . ?
C11 C12 C13 C8 -0.7(3) . . . . ?
C9 C8 C13 F13 179.07(18) . . . . ?
C7 C8 C13 F13 6.7(3) . . . . ?
C9 C8 C13 C12 0.7(3) . . . . ?
C7 C8 C13 C12 -171.7(2) . . . . ?

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
O14 H14A Br1 0.840(18) 2.450(19) 3.283(2) 171(3) .
O14 H14B Br1 0.844(18) 2.531(19) 3.372(2) 175(3) 3_666

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.563
_refine_diff_density_rms         0.055

# Attachment '- 2e_mm-302-5.cif'

data_2e
_database_code_depnum_ccdc_archive 'CCDC 817435'
#TrackingRef '- 2e_mm-302-5.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C13 H16 F3 N2), H2 O, 2(Br)'
_chemical_formula_sum            'C26 H34 Br2 F6 N4 O'
_chemical_formula_weight         692.39

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           monoclinic
_symmetry_space_group_name_H-M   C2/c

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                   10.4807(2)
_cell_length_b                   10.1629(2)
_cell_length_c                   27.0117(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.7020(10)
_cell_angle_gamma                90.00
_cell_volume                     2862.90(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3725
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1400
_exptl_absorpt_coefficient_mu    2.898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6235
_exptl_absorpt_correction_T_max  0.8229
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(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  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2596
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         25.24
_reflns_number_total             2596
_reflns_number_gt                2384
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, <i>et al.</i>, 2008);
POV-RAY (Cason, 2004)
;
_computing_publication_material  SHELXL-97

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0000P)^2^+18.3544P] where P=(Fo^2^+2Fc^2^)/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         2596
_refine_ls_number_parameters     182
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1032
_refine_ls_wR_factor_gt          0.1015
_refine_ls_goodness_of_fit_ref   1.236
_refine_ls_restrained_S_all      1.237
_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 0.32372(5) 0.52900(5) 0.67010(2) 0.02360(16) Uani 1 1 d . . .
F10 F 0.6370(3) 0.0668(3) 0.49233(12) 0.0350(8) Uani 1 1 d . . .
F11 F 0.4418(3) 0.1999(3) 0.44367(11) 0.0352(8) Uani 1 1 d . . .
F12 F 0.3204(3) 0.3893(3) 0.49069(11) 0.0342(8) Uani 1 1 d . . .
N1 N 0.7066(4) 0.4253(4) 0.65246(14) 0.0138(8) Uani 1 1 d . . .
N2 N 0.8828(4) 0.5986(4) 0.67189(16) 0.0226(9) Uani 1 1 d . . .
C1 C 0.6645(5) 0.5563(5) 0.6308(2) 0.0243(12) Uani 1 1 d . . .
H1A H 0.5942 0.5925 0.6487 0.029 Uiso 1 1 calc R . .
H1B H 0.6327 0.5463 0.5953 0.029 Uiso 1 1 calc R . .
C2 C 0.7806(6) 0.6500(6) 0.6363(3) 0.0354(15) Uani 1 1 d . . .
H2A H 0.8137 0.6616 0.6035 0.042 Uiso 1 1 calc R . .
H2B H 0.7532 0.7372 0.6477 0.042 Uiso 1 1 calc R . .
C3 C 0.9362(5) 0.4795(6) 0.6512(2) 0.0343(14) Uani 1 1 d . . .
H3A H 0.9933 0.4348 0.6774 0.041 Uiso 1 1 calc R . .
H3B H 0.9879 0.5041 0.6239 0.041 Uiso 1 1 calc R . .
C4 C 0.8282(5) 0.3849(5) 0.63124(19) 0.0201(11) Uani 1 1 d . . .
H4A H 0.8161 0.3889 0.5945 0.024 Uiso 1 1 calc R . .
H4B H 0.8510 0.2934 0.6412 0.024 Uiso 1 1 calc R . .
C5 C 0.7357(5) 0.4420(5) 0.70804(18) 0.0233(12) Uani 1 1 d U . .
H5A H 0.7784 0.3622 0.7227 0.028 Uiso 1 1 calc R . .
H5B H 0.6553 0.4561 0.7237 0.028 Uiso 1 1 calc R . .
C6 C 0.8252(6) 0.5631(6) 0.7171(2) 0.0368(15) Uani 1 1 d U . .
H6A H 0.7753 0.6386 0.7281 0.044 Uiso 1 1 calc R . .
H6B H 0.8937 0.5428 0.7439 0.044 Uiso 1 1 calc R . .
C7 C 0.6023(5) 0.3212(5) 0.64371(18) 0.0160(10) Uani 1 1 d . . .
H7A H 0.6329 0.2390 0.6606 0.019 Uiso 1 1 calc R . .
H7B H 0.5258 0.3511 0.6593 0.019 Uiso 1 1 calc R . .
C8 C 0.5631(5) 0.2914(5) 0.58966(17) 0.0159(10) Uani 1 1 d . . .
C9 C 0.6233(5) 0.1923(5) 0.56514(19) 0.0204(11) Uani 1 1 d . . .
H9 H 0.6924 0.1444 0.5820 0.024 Uiso 1 1 calc R . .
C10 C 0.5824(5) 0.1643(5) 0.5166(2) 0.0236(12) Uani 1 1 d . . .
C11 C 0.4812(5) 0.2307(5) 0.49118(17) 0.0231(11) Uani 1 1 d . . .
C12 C 0.4227(5) 0.3274(5) 0.51568(19) 0.0203(11) Uani 1 1 d . . .
C13 C 0.4598(5) 0.3598(5) 0.56424(18) 0.0180(10) Uani 1 1 d . . .
H13 H 0.4166 0.4271 0.5804 0.022 Uiso 1 1 calc R . .
O1 O 0.5000 0.7261(7) 0.7500 0.0492(19) Uani 1 2 d SD . .
H1O H 0.462(8) 0.677(8) 0.730(3) 0.074 Uiso 1 1 d D . .

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 0.0261(3) 0.0247(3) 0.0201(2) 0.0012(2) 0.0027(2) 0.0076(3)
F10 0.042(2) 0.0370(19) 0.0258(17) -0.0100(14) 0.0012(14) 0.0201(16)
F11 0.044(2) 0.041(2) 0.0190(16) -0.0069(14) -0.0044(15) 0.0129(17)
F12 0.0292(18) 0.047(2) 0.0245(17) -0.0044(15) -0.0084(14) 0.0169(16)
N1 0.0112(19) 0.0140(19) 0.016(2) 0.0011(15) -0.0019(16) -0.0043(16)
N2 0.014(2) 0.028(2) 0.025(2) -0.0028(19) 0.0016(19) -0.0049(19)
C1 0.027(3) 0.018(3) 0.027(3) 0.006(2) -0.001(2) -0.001(2)
C2 0.032(4) 0.022(3) 0.050(4) 0.006(3) -0.008(3) -0.008(3)
C3 0.022(3) 0.031(3) 0.051(4) -0.007(3) 0.011(3) -0.005(3)
C4 0.015(3) 0.022(3) 0.024(3) -0.002(2) 0.007(2) -0.002(2)
C5 0.025(3) 0.028(3) 0.016(2) 0.001(2) 0.000(2) -0.006(2)
C6 0.032(3) 0.047(4) 0.030(3) -0.007(3) 0.000(3) -0.017(3)
C7 0.014(3) 0.014(2) 0.020(3) 0.0014(19) 0.0020(19) -0.0059(19)
C8 0.018(2) 0.016(2) 0.015(2) 0.0014(19) 0.004(2) -0.004(2)
C9 0.021(3) 0.020(3) 0.020(3) 0.001(2) 0.000(2) 0.003(2)
C10 0.030(3) 0.017(3) 0.024(3) -0.005(2) 0.004(2) 0.007(2)
C11 0.029(3) 0.027(3) 0.012(2) -0.002(2) -0.003(2) 0.000(2)
C12 0.013(2) 0.026(3) 0.021(3) 0.005(2) -0.003(2) 0.003(2)
C13 0.019(3) 0.016(2) 0.019(2) -0.0030(19) 0.003(2) 0.001(2)
O1 0.052(5) 0.031(4) 0.061(5) 0.000 -0.013(4) 0.000

_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
F10 C10 1.347(6) . ?
F11 C11 1.345(5) . ?
F12 C12 1.363(6) . ?
N1 C1 1.503(6) . ?
N1 C4 1.506(6) . ?
N1 C5 1.512(6) . ?
N1 C7 1.522(6) . ?
N2 C6 1.461(7) . ?
N2 C2 1.463(7) . ?
N2 C3 1.467(7) . ?
C1 C2 1.541(7) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.541(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.552(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.507(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.391(7) . ?
C8 C13 1.407(7) . ?
C9 C10 1.369(7) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(8) . ?
C11 C12 1.364(7) . ?
C12 C13 1.371(7) . ?
C13 H13 0.9500 . ?
O1 H1O 0.81(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 108.7(4) . . ?
C1 N1 C5 108.0(4) . . ?
C4 N1 C5 108.3(4) . . ?
C1 N1 C7 112.1(4) . . ?
C4 N1 C7 111.9(4) . . ?
C5 N1 C7 107.7(4) . . ?
C6 N2 C2 107.5(5) . . ?
C6 N2 C3 108.7(5) . . ?
C2 N2 C3 109.0(5) . . ?
N1 C1 C2 108.1(4) . . ?
N1 C1 H1A 110.1 . . ?
C2 C1 H1A 110.1 . . ?
N1 C1 H1B 110.1 . . ?
C2 C1 H1B 110.1 . . ?
H1A C1 H1B 108.4 . . ?
N2 C2 C1 111.2(4) . . ?
N2 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
N2 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N2 C3 C4 110.7(4) . . ?
N2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
N1 C4 C3 108.4(4) . . ?
N1 C4 H4A 110.0 . . ?
C3 C4 H4A 110.0 . . ?
N1 C4 H4B 110.0 . . ?
C3 C4 H4B 110.0 . . ?
H4A C4 H4B 108.4 . . ?
N1 C5 C6 107.8(4) . . ?
N1 C5 H5A 110.1 . . ?
C6 C5 H5A 110.1 . . ?
N1 C5 H5B 110.1 . . ?
C6 C5 H5B 110.1 . . ?
H5A C5 H5B 108.5 . . ?
N2 C6 C5 110.9(4) . . ?
N2 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 N1 114.3(4) . . ?
C8 C7 H7A 108.7 . . ?
N1 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
N1 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 C13 119.3(4) . . ?
C9 C8 C7 120.9(4) . . ?
C13 C8 C7 119.7(4) . . ?
C10 C9 C8 119.5(5) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
F10 C10 C9 120.8(5) . . ?
F10 C10 C11 117.4(5) . . ?
C9 C10 C11 121.8(5) . . ?
F11 C11 C12 121.3(5) . . ?
F11 C11 C10 120.6(5) . . ?
C12 C11 C10 118.1(4) . . ?
F12 C12 C11 117.5(4) . . ?
F12 C12 C13 119.8(5) . . ?
C11 C12 C13 122.6(5) . . ?
C12 C13 C8 118.7(5) . . ?
C12 C13 H13 120.7 . . ?
C8 C13 H13 120.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 -49.4(5) . . . . ?
C5 N1 C1 C2 67.9(6) . . . . ?
C7 N1 C1 C2 -173.7(4) . . . . ?
C6 N2 C2 C1 -50.1(6) . . . . ?
C3 N2 C2 C1 67.5(6) . . . . ?
N1 C1 C2 N2 -15.8(7) . . . . ?
C6 N2 C3 C4 68.5(6) . . . . ?
C2 N2 C3 C4 -48.4(6) . . . . ?
C1 N1 C4 C3 67.7(5) . . . . ?
C5 N1 C4 C3 -49.4(5) . . . . ?
C7 N1 C4 C3 -168.0(4) . . . . ?
N2 C3 C4 N1 -16.4(6) . . . . ?
C1 N1 C5 C6 -49.7(5) . . . . ?
C4 N1 C5 C6 67.9(5) . . . . ?
C7 N1 C5 C6 -170.9(4) . . . . ?
C2 N2 C6 C5 69.0(6) . . . . ?
C3 N2 C6 C5 -48.9(6) . . . . ?
N1 C5 C6 N2 -16.6(6) . . . . ?
C1 N1 C7 C8 62.1(5) . . . . ?
C4 N1 C7 C8 -60.3(5) . . . . ?
C5 N1 C7 C8 -179.3(4) . . . . ?
N1 C7 C8 C9 90.9(5) . . . . ?
N1 C7 C8 C13 -92.5(5) . . . . ?
C13 C8 C9 C10 0.9(7) . . . . ?
C7 C8 C9 C10 177.5(5) . . . . ?
C8 C9 C10 F10 -178.4(5) . . . . ?
C8 C9 C10 C11 -0.9(8) . . . . ?
F10 C10 C11 F11 -1.5(8) . . . . ?
C9 C10 C11 F11 -179.1(5) . . . . ?
F10 C10 C11 C12 178.3(5) . . . . ?
C9 C10 C11 C12 0.7(9) . . . . ?
F11 C11 C12 F12 1.8(8) . . . . ?
C10 C11 C12 F12 -178.0(5) . . . . ?
F11 C11 C12 C13 179.2(5) . . . . ?
C10 C11 C12 C13 -0.6(9) . . . . ?
F12 C12 C13 C8 178.0(5) . . . . ?
C11 C12 C13 C8 0.6(8) . . . . ?
C9 C8 C13 C12 -0.8(7) . . . . ?
C7 C8 C13 C12 -177.5(5) . . . . ?

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
O1 H1O Br1 0.81(7) 2.55(7) 3.360(4) 175(9) .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.677
_refine_diff_density_min         -1.392
_refine_diff_density_rms         0.110

# Attachment '- 2f_mm-323-1.cif'

data_2f
_database_code_depnum_ccdc_archive 'CCDC 817436'
#TrackingRef '- 2f_mm-323-1.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C13 H16 F3 N2), H2 O, 2(Br)'
_chemical_formula_sum            'C26 H34 Br2 F6 N4 O'
_chemical_formula_weight         692.39

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           monoclinic
_symmetry_space_group_name_H-M   P21/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.4502(5)
_cell_length_b                   6.6042(2)
_cell_length_c                   15.5119(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.280(3)
_cell_angle_gamma                90.00
_cell_volume                     1377.87(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    3429
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             700
_exptl_absorpt_coefficient_mu    3.010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5572
_exptl_absorpt_correction_T_max  0.8400
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(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  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7888
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2485
_reflns_number_gt                2088
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, <i>et al.</i>, 2008);
POV-RAY (Cason, 2004)
;
_computing_publication_material  SHELXL-97

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0157P)^2^+1.2892P] where P=(Fo^2^+2Fc^2^)/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         2485
_refine_ls_number_parameters     187
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0655
_refine_ls_wR_factor_gt          0.0611
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.22671(2) 0.01863(4) 0.454282(17) 0.03161(10) Uani 1 1 d . . .
F9 F 0.40838(10) 0.8572(2) 0.62697(9) 0.0286(3) Uani 1 1 d . . .
F10 F 0.58927(11) 0.8305(2) 0.69499(10) 0.0305(4) Uani 1 1 d . . .
F11 F 0.69167(11) 0.4785(2) 0.69062(10) 0.0332(4) Uani 1 1 d . . .
N1 N 0.21804(14) 0.4999(3) 0.61446(12) 0.0183(4) Uani 1 1 d . . .
N2 N 0.06658(15) 0.4695(3) 0.71385(14) 0.0256(5) Uani 1 1 d . . .
C1 C 0.21730(18) 0.6711(4) 0.67860(16) 0.0254(6) Uani 1 1 d . . .
H1A H 0.2180 0.8026 0.6480 0.031 Uiso 1 1 calc R . .
H1B H 0.2771 0.6637 0.7159 0.031 Uiso 1 1 calc R . .
C2 C 0.12248(19) 0.6539(4) 0.73396(16) 0.0261(6) Uani 1 1 d . . .
H2A H 0.1413 0.6531 0.7957 0.031 Uiso 1 1 calc R . .
H2B H 0.0797 0.7734 0.7235 0.031 Uiso 1 1 calc R . .
C3 C 0.13220(19) 0.2948(4) 0.72518(16) 0.0266(6) Uani 1 1 d . . .
H3A H 0.0940 0.1690 0.7149 0.032 Uiso 1 1 calc R . .
H3B H 0.1571 0.2918 0.7853 0.032 Uiso 1 1 calc R . .
C4 C 0.22132(18) 0.3022(4) 0.66299(15) 0.0220(5) Uani 1 1 d . . .
H4A H 0.2844 0.2915 0.6959 0.026 Uiso 1 1 calc R . .
H4B H 0.2178 0.1874 0.6220 0.026 Uiso 1 1 calc R . .
C5 C 0.12272(18) 0.5071(4) 0.56218(16) 0.0248(6) Uani 1 1 d . . .
H5A H 0.1228 0.3980 0.5184 0.030 Uiso 1 1 calc R . .
H5B H 0.1173 0.6387 0.5320 0.030 Uiso 1 1 calc R . .
C6 C 0.03388(19) 0.4794(5) 0.62354(17) 0.0333(7) Uani 1 1 d . . .
H6A H -0.0128 0.5940 0.6162 0.040 Uiso 1 1 calc R . .
H6B H -0.0019 0.3532 0.6085 0.040 Uiso 1 1 calc R . .
C7 C 0.30380(18) 0.5197(4) 0.55127(15) 0.0214(5) Uani 1 1 d . . .
H7A H 0.2976 0.4116 0.5074 0.026 Uiso 1 1 calc R . .
H7B H 0.2978 0.6513 0.5211 0.026 Uiso 1 1 calc R . .
C8 C 0.40563(17) 0.5066(3) 0.59179(15) 0.0196(5) Uani 1 1 d . . .
C9 C 0.45343(18) 0.6741(4) 0.62606(16) 0.0213(5) Uani 1 1 d . . .
C10 C 0.54780(18) 0.6639(4) 0.66025(16) 0.0238(5) Uani 1 1 d . . .
C11 C 0.59803(18) 0.4834(4) 0.65807(16) 0.0251(6) Uani 1 1 d . . .
C12 C 0.55538(19) 0.3125(4) 0.62334(16) 0.0269(6) Uani 1 1 d . . .
H12 H 0.5908 0.1881 0.6219 0.032 Uiso 1 1 calc R . .
C13 C 0.45951(19) 0.3255(4) 0.59046(16) 0.0240(5) Uani 1 1 d . . .
H13 H 0.4296 0.2081 0.5663 0.029 Uiso 1 1 calc R . .
O1 O 0.0248(4) -0.0271(9) 0.5671(3) 0.0595(14) Uani 0.50 1 d PD A -1
H1O H -0.037(2) -0.019(13) 0.557(6) 0.089 Uiso 0.50 1 d PD B -1
H1P H 0.044(6) -0.012(14) 0.516(2) 0.089 Uiso 0.50 1 d PD C -1

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 0.03512(17) 0.03029(16) 0.02939(15) -0.00524(12) -0.00297(11) 0.00497(13)
F9 0.0241(8) 0.0200(7) 0.0417(9) -0.0008(7) -0.0016(7) 0.0020(6)
F10 0.0276(8) 0.0288(8) 0.0352(8) 0.0000(7) -0.0027(6) -0.0059(7)
F11 0.0210(7) 0.0418(9) 0.0366(9) 0.0074(7) -0.0044(6) 0.0018(7)
N1 0.0161(9) 0.0226(11) 0.0163(9) 0.0009(8) -0.0002(8) -0.0004(9)
N2 0.0181(10) 0.0335(12) 0.0252(11) 0.0000(9) 0.0015(8) -0.0010(9)
C1 0.0247(14) 0.0249(13) 0.0268(13) -0.0070(11) 0.0009(11) -0.0006(11)
C2 0.0254(14) 0.0269(14) 0.0258(13) -0.0021(11) 0.0040(11) 0.0027(11)
C3 0.0264(14) 0.0262(14) 0.0271(14) 0.0025(11) 0.0048(11) -0.0053(11)
C4 0.0210(13) 0.0230(13) 0.0219(12) 0.0036(10) -0.0001(10) 0.0002(10)
C5 0.0197(12) 0.0328(15) 0.0218(12) 0.0017(11) -0.0044(10) 0.0014(11)
C6 0.0188(13) 0.0529(19) 0.0282(14) -0.0005(13) -0.0014(11) -0.0019(13)
C7 0.0222(12) 0.0249(13) 0.0173(11) 0.0002(10) 0.0041(9) -0.0005(10)
C8 0.0192(12) 0.0213(13) 0.0183(11) 0.0018(10) 0.0062(9) -0.0004(10)
C9 0.0173(12) 0.0199(13) 0.0269(13) 0.0030(10) 0.0050(10) 0.0031(10)
C10 0.0238(14) 0.0240(13) 0.0237(13) 0.0012(11) 0.0028(10) -0.0050(11)
C11 0.0190(12) 0.0334(15) 0.0228(12) 0.0090(11) 0.0009(10) 0.0028(11)
C12 0.0266(14) 0.0237(14) 0.0303(14) 0.0066(11) 0.0090(11) 0.0061(11)
C13 0.0268(14) 0.0205(13) 0.0249(13) -0.0003(10) 0.0072(11) -0.0013(11)
O1 0.042(3) 0.090(4) 0.046(3) 0.006(3) 0.002(2) 0.012(3)

_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
F9 C9 1.353(3) . ?
F10 C10 1.345(3) . ?
F11 C11 1.355(3) . ?
N1 C1 1.506(3) . ?
N1 C4 1.508(3) . ?
N1 C5 1.514(3) . ?
N1 C7 1.523(3) . ?
N2 C3 1.462(3) . ?
N2 C2 1.464(3) . ?
N2 C6 1.468(3) . ?
C1 C2 1.545(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.543(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.542(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.507(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.384(3) . ?
C8 C13 1.398(3) . ?
C9 C10 1.375(3) . ?
C10 C11 1.371(3) . ?
C11 C12 1.375(4) . ?
C12 C13 1.387(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
O1 H1O 0.84(2) . ?
O1 H1P 0.84(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
C1 N1 C4 108.70(18) . . ?
C1 N1 C5 108.79(18) . . ?
C4 N1 C5 108.47(18) . . ?
C1 N1 C7 111.62(18) . . ?
C4 N1 C7 112.02(17) . . ?
C5 N1 C7 107.14(17) . . ?
C3 N2 C2 108.75(19) . . ?
C3 N2 C6 109.1(2) . . ?
C2 N2 C6 108.5(2) . . ?
N1 C1 C2 108.66(19) . . ?
N1 C1 H1A 110.0 . . ?
C2 C1 H1A 110.0 . . ?
N1 C1 H1B 110.0 . . ?
C2 C1 H1B 110.0 . . ?
H1A C1 H1B 108.3 . . ?
N2 C2 C1 111.5(2) . . ?
N2 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
N2 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
N2 C3 C4 111.7(2) . . ?
N2 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
N2 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
N1 C4 C3 108.56(19) . . ?
N1 C4 H4A 110.0 . . ?
C3 C4 H4A 110.0 . . ?
N1 C4 H4B 110.0 . . ?
C3 C4 H4B 110.0 . . ?
H4A C4 H4B 108.4 . . ?
N1 C5 C6 108.81(19) . . ?
N1 C5 H5A 109.9 . . ?
C6 C5 H5A 109.9 . . ?
N1 C5 H5B 109.9 . . ?
C6 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
N2 C6 C5 111.4(2) . . ?
N2 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 N1 114.62(19) . . ?
C8 C7 H7A 108.6 . . ?
N1 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
N1 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 C13 116.7(2) . . ?
C9 C8 C7 122.3(2) . . ?
C13 C8 C7 120.9(2) . . ?
F9 C9 C10 116.9(2) . . ?
F9 C9 C8 120.8(2) . . ?
C10 C9 C8 122.4(2) . . ?
F10 C10 C11 121.2(2) . . ?
F10 C10 C9 119.7(2) . . ?
C11 C10 C9 119.1(2) . . ?
F11 C11 C10 118.0(2) . . ?
F11 C11 C12 120.8(2) . . ?
C10 C11 C12 121.3(2) . . ?
C11 C12 C13 118.6(2) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C12 C13 C8 121.9(2) . . ?
C12 C13 H13 119.0 . . ?
C8 C13 H13 119.0 . . ?
H1O O1 H1P 97(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 -62.0(2) . . . . ?
C5 N1 C1 C2 56.0(2) . . . . ?
C7 N1 C1 C2 173.97(19) . . . . ?
C3 N2 C2 C1 56.0(3) . . . . ?
C6 N2 C2 C1 -62.6(3) . . . . ?
N1 C1 C2 N2 5.2(3) . . . . ?
C2 N2 C3 C4 -62.1(3) . . . . ?
C6 N2 C3 C4 56.1(3) . . . . ?
C1 N1 C4 C3 56.2(2) . . . . ?
C5 N1 C4 C3 -61.9(2) . . . . ?
C7 N1 C4 C3 -179.96(19) . . . . ?
N2 C3 C4 N1 5.1(3) . . . . ?
C1 N1 C5 C6 -61.3(2) . . . . ?
C4 N1 C5 C6 56.8(2) . . . . ?
C7 N1 C5 C6 177.9(2) . . . . ?
C3 N2 C6 C5 -61.4(3) . . . . ?
C2 N2 C6 C5 56.9(3) . . . . ?
N1 C5 C6 N2 4.1(3) . . . . ?
C1 N1 C7 C8 63.5(2) . . . . ?
C4 N1 C7 C8 -58.6(2) . . . . ?
C5 N1 C7 C8 -177.48(19) . . . . ?
N1 C7 C8 C9 -86.3(3) . . . . ?
N1 C7 C8 C13 98.6(3) . . . . ?
C13 C8 C9 F9 177.5(2) . . . . ?
C7 C8 C9 F9 2.2(3) . . . . ?
C13 C8 C9 C10 -2.3(4) . . . . ?
C7 C8 C9 C10 -177.6(2) . . . . ?
F9 C9 C10 F10 2.2(3) . . . . ?
C8 C9 C10 F10 -178.0(2) . . . . ?
F9 C9 C10 C11 -177.7(2) . . . . ?
C8 C9 C10 C11 2.1(4) . . . . ?
F10 C10 C11 F11 -1.2(4) . . . . ?
C9 C10 C11 F11 178.7(2) . . . . ?
F10 C10 C11 C12 179.4(2) . . . . ?
C9 C10 C11 C12 -0.8(4) . . . . ?
F11 C11 C12 C13 -179.7(2) . . . . ?
C10 C11 C12 C13 -0.2(4) . . . . ?
C11 C12 C13 C8 0.0(4) . . . . ?
C9 C8 C13 C12 1.3(4) . . . . ?
C7 C8 C13 C12 176.6(2) . . . . ?

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
O1 H1P Br1 0.84(2) 2.65(7) 3.252(5) 130(7) .
O1 H1O Br1 0.84(2) 2.56(2) 3.398(5) 172(9) 3_556

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.060

# Attachment '- 2g_mm-308-1.cif'

data_2g
_database_code_depnum_ccdc_archive 'CCDC 817437'
#TrackingRef '- 2g_mm-308-1.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H17 F2 N2, H2 O, Br'
_chemical_formula_sum            'C13 H19 Br F2 N2 O'
_chemical_formula_weight         337.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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   P21/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   20.7208(5)
_cell_length_b                   7.0528(2)
_cell_length_c                   20.7259(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.7000(10)
_cell_angle_gamma                90.00
_cell_volume                     2773.43(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    7157
_cell_measurement_theta_max      28.283
_cell_measurement_theta_min      0.407

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    2.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6470
_exptl_absorpt_correction_T_max  0.8185
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(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  'Bruker-Nonius Kappa CCD with APEXII detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9971
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0429
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         25.25
_reflns_number_total             5018
_reflns_number_gt                4008
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'Collect (Bruker, 2008)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        DENZO-SMN
_computing_structure_solution    'SIR-2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, 1997); MERCURY (Macrae, <i>et al.</i>, 2008);
POV-RAY (Cason, 2004)
;
_computing_publication_material  SHELXL-97

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0148P)^2^+2.6479P] where P=(Fo^2^+2Fc^2^)/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         5018
_refine_ls_number_parameters     356
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0661
_refine_ls_wR_factor_gt          0.0601
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 1.03983(6) 0.76011(11) 0.27151(6) 0.0245(2) Uani 1 1 d . . .
Br2 Br 0.27116(6) 0.76343(9) 0.53958(6) 0.0241(2) Uani 1 1 d . . .
F10 F 0.65840(15) 1.0379(4) 0.63519(16) 0.0346(8) Uani 1 1 d . . .
F12 F 0.68810(15) 0.3897(4) 0.68529(16) 0.0334(8) Uani 1 1 d . . .
N1 N 0.8949(4) 0.7292(5) 0.6063(4) 0.0161(16) Uani 1 1 d . . .
N2 N 0.9205(3) 0.7066(6) 0.4951(3) 0.0196(12) Uani 1 1 d . . .
C1 C 0.8643(4) 0.8992(7) 0.5593(3) 0.0177(14) Uani 1 1 d . . .
H1A H 0.8856 1.0172 0.5848 0.021 Uiso 1 1 calc R . .
H1B H 0.8128 0.9050 0.5458 0.021 Uiso 1 1 calc R . .
C2 C 0.8796(4) 0.8810(7) 0.4938(3) 0.0217(14) Uani 1 1 d . . .
H2A H 0.8346 0.8784 0.4516 0.026 Uiso 1 1 calc R . .
H2B H 0.9066 0.9934 0.4900 0.026 Uiso 1 1 calc R . .
C3 C 0.8784(4) 0.5425(7) 0.5003(3) 0.0236(14) Uani 1 1 d . . .
H3A H 0.9047 0.4241 0.5017 0.028 Uiso 1 1 calc R . .
H3B H 0.8337 0.5380 0.4578 0.028 Uiso 1 1 calc R . .
C4 C 0.8622(4) 0.5533(7) 0.5656(4) 0.0212(15) Uani 1 1 d . . .
H4A H 0.8106 0.5560 0.5515 0.025 Uiso 1 1 calc R . .
H4B H 0.8814 0.4401 0.5954 0.025 Uiso 1 1 calc R . .
C5 C 0.9730(5) 0.7242(7) 0.6253(5) 0.0197(18) Uani 1 1 d . . .
H5A H 0.9941 0.6132 0.6557 0.024 Uiso 1 1 calc R . .
H5B H 0.9953 0.8402 0.6517 0.024 Uiso 1 1 calc R . .
C6 C 0.9866(4) 0.7113(8) 0.5586(4) 0.0243(15) Uani 1 1 d . . .
H6A H 1.0150 0.8219 0.5562 0.029 Uiso 1 1 calc R . .
H6B H 1.0142 0.5952 0.5604 0.029 Uiso 1 1 calc R . .
C7 C 0.8843(5) 0.7440(5) 0.6737(5) 0.018(2) Uani 1 1 d . . .
H7A H 0.9049 0.8655 0.6967 0.021 Uiso 1 1 calc R . .
H7B H 0.9113 0.6408 0.7054 0.021 Uiso 1 1 calc R . .
C8 C 0.8087(5) 0.7341(6) 0.6674(5) 0.0156(18) Uani 1 1 d . . .
C9 C 0.7674(3) 0.8967(8) 0.6529(3) 0.0213(14) Uani 1 1 d . . .
H9 H 0.7853 1.0149 0.6456 0.026 Uiso 1 1 calc R . .
C10 C 0.6993(3) 0.8821(7) 0.6496(3) 0.0231(13) Uani 1 1 d . . .
C11 C 0.6719(3) 0.7142(8) 0.6616(3) 0.0235(13) Uani 1 1 d . . .
H11 H 0.6259 0.7078 0.6612 0.028 Uiso 1 1 calc R . .
C12 C 0.7141(3) 0.5569(7) 0.6744(3) 0.0255(13) Uani 1 1 d . . .
C13 C 0.7816(3) 0.5626(7) 0.6770(3) 0.0187(13) Uani 1 1 d . . .
H13 H 0.8090 0.4503 0.6853 0.022 Uiso 1 1 calc R . .
N1A N 0.6060(4) 0.7584(5) 0.3935(4) 0.0147(16) Uani 1 1 d . . .
N2A N 0.4944(3) 0.7755(6) 0.4181(3) 0.0214(13) Uani 1 1 d . . .
F10A F 0.67887(16) 0.3634(4) 0.19239(16) 0.0377(9) Uani 1 1 d . . .
F12A F 0.64258(18) 1.0139(4) 0.15599(15) 0.0365(9) Uani 1 1 d . . .
C1A C 0.6259(5) 0.7702(7) 0.4724(5) 0.0200(18) Uani 1 1 d . . .
H1A1 H 0.6534 0.8870 0.4917 0.024 Uiso 1 1 calc R . .
H1A2 H 0.6552 0.6596 0.4964 0.024 Uiso 1 1 calc R . .
C2A C 0.5567(4) 0.7725(7) 0.4851(4) 0.0198(15) Uani 1 1 d . . .
H2A1 H 0.5551 0.6587 0.5123 0.024 Uiso 1 1 calc R . .
H2A2 H 0.5564 0.8858 0.5132 0.024 Uiso 1 1 calc R . .
C3A C 0.4938(3) 0.6034(9) 0.3789(3) 0.0232(14) Uani 1 1 d . . .
H3A1 H 0.4525 0.6058 0.3332 0.028 Uiso 1 1 calc R . .
H3A2 H 0.4892 0.4918 0.4057 0.028 Uiso 1 1 calc R . .
C4A C 0.5624(4) 0.5830(8) 0.3653(4) 0.0205(14) Uani 1 1 d . . .
H4A1 H 0.5891 0.4690 0.3895 0.025 Uiso 1 1 calc R . .
H4A2 H 0.5504 0.5701 0.3142 0.025 Uiso 1 1 calc R . .
C5A C 0.5640(3) 0.9332(8) 0.3593(4) 0.0176(13) Uani 1 1 d . . .
H5A1 H 0.5491 0.9273 0.3076 0.021 Uiso 1 1 calc R . .
H5A2 H 0.5932 1.0482 0.3771 0.021 Uiso 1 1 calc R . .
C6A C 0.4984(4) 0.9412(8) 0.3775(4) 0.0247(14) Uani 1 1 d . . .
H6A1 H 0.5005 1.0575 0.4051 0.030 Uiso 1 1 calc R . .
H6A2 H 0.4553 0.9477 0.3334 0.030 Uiso 1 1 calc R . .
C7A C 0.6756(5) 0.7499(6) 0.3838(6) 0.019(2) Uani 1 1 d . . .
H7A1 H 0.7028 0.8671 0.4033 0.023 Uiso 1 1 calc R . .
H7A2 H 0.7038 0.6415 0.4112 0.023 Uiso 1 1 calc R . .
C8A C 0.6659(5) 0.7292(7) 0.3086(5) 0.0202(19) Uani 1 1 d . . .
C9A C 0.6741(3) 0.5494(7) 0.2838(3) 0.0231(14) Uani 1 1 d . . .
H9A H 0.6815 0.4402 0.3128 0.028 Uiso 1 1 calc R . .
C10A C 0.6710(3) 0.5361(7) 0.2169(3) 0.0236(12) Uani 1 1 d . . .
C11A C 0.6617(3) 0.6895(8) 0.1723(3) 0.0263(14) Uani 1 1 d . . .
H11A H 0.6608 0.6761 0.1263 0.032 Uiso 1 1 calc R . .
C12A C 0.6539(3) 0.8625(7) 0.1990(3) 0.0247(13) Uani 1 1 d . . .
C13A C 0.6558(3) 0.8884(7) 0.2652(3) 0.0203(13) Uani 1 1 d . . .
H13A H 0.6505 1.0111 0.2813 0.024 Uiso 1 1 calc R . .
O1 O 0.9960(2) 0.8173(7) 0.4092(2) 0.0379(11) Uani 1 1 d D . .
H1O H 0.994(5) 0.772(7) 0.372(2) 0.057 Uiso 1 1 d D . .
H1P H 0.971(3) 0.763(7) 0.427(3) 0.057 Uiso 1 1 d D . .
O2 O 0.4107(2) 0.6978(7) 0.4981(3) 0.0400(11) Uani 1 1 d D . .
H2O H 0.412(3) 0.739(8) 0.461(2) 0.060 Uiso 1 1 d D . .
H2P H 0.3684(16) 0.706(8) 0.492(5) 0.060 Uiso 1 1 d D . .

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 0.0327(6) 0.0181(3) 0.0212(6) 0.00016(18) 0.0095(4) 0.00113(18)
Br2 0.0217(6) 0.0178(3) 0.0313(6) 0.0002(2) 0.0092(4) -0.00204(19)
F10 0.0324(17) 0.0246(14) 0.051(2) 0.0000(13) 0.0209(16) 0.0101(12)
F12 0.0367(18) 0.0266(15) 0.0385(18) 0.0042(12) 0.0169(15) -0.0114(12)
N1 0.019(4) 0.016(2) 0.013(4) 0.0011(16) 0.006(3) 0.0017(18)
N2 0.019(3) 0.0194(18) 0.023(3) -0.002(2) 0.011(2) -0.001(2)
C1 0.020(3) 0.010(2) 0.022(3) 0.000(2) 0.007(3) 0.000(2)
C2 0.025(3) 0.021(3) 0.020(3) 0.004(2) 0.009(3) -0.003(3)
C3 0.025(3) 0.022(3) 0.027(3) -0.007(2) 0.014(3) -0.009(2)
C4 0.025(3) 0.017(3) 0.023(3) -0.007(2) 0.011(3) -0.006(3)
C5 0.015(4) 0.018(2) 0.024(4) -0.003(2) 0.005(3) -0.002(2)
C6 0.020(4) 0.024(2) 0.026(4) 0.004(3) 0.006(3) -0.002(3)
C7 0.016(5) 0.016(3) 0.017(5) -0.0031(16) 0.003(4) -0.0001(17)
C8 0.018(4) 0.016(3) 0.012(4) -0.0013(18) 0.005(3) -0.0023(19)
C9 0.026(3) 0.018(3) 0.023(3) -0.004(2) 0.013(3) -0.003(2)
C10 0.026(3) 0.021(3) 0.022(3) -0.004(2) 0.009(3) 0.006(2)
C11 0.013(3) 0.039(3) 0.018(3) 0.001(3) 0.006(2) 0.003(3)
C12 0.033(3) 0.025(3) 0.022(3) -0.003(2) 0.014(3) -0.007(2)
C13 0.024(3) 0.020(3) 0.013(3) 0.000(2) 0.009(3) 0.000(2)
N1A 0.019(4) 0.012(2) 0.014(3) 0.0007(14) 0.008(3) -0.0010(14)
N2A 0.017(3) 0.030(2) 0.019(3) 0.005(2) 0.008(2) 0.000(2)
F10A 0.046(2) 0.0276(15) 0.0406(19) -0.0153(13) 0.0184(17) 0.0039(13)
F12A 0.059(2) 0.0276(15) 0.0248(16) 0.0065(12) 0.0194(16) 0.0003(15)
C1A 0.016(4) 0.029(3) 0.016(4) 0.001(2) 0.007(3) -0.005(2)
C2A 0.019(3) 0.028(3) 0.017(3) 0.004(2) 0.011(3) 0.004(2)
C3A 0.016(3) 0.034(3) 0.021(3) 0.002(3) 0.008(2) -0.004(2)
C4A 0.019(3) 0.019(2) 0.024(3) -0.004(2) 0.010(3) -0.007(2)
C5A 0.015(3) 0.019(3) 0.021(3) 0.004(2) 0.009(3) 0.003(2)
C6A 0.021(3) 0.032(3) 0.023(3) 0.001(2) 0.011(3) 0.006(2)
C7A 0.009(5) 0.023(4) 0.031(6) 0.0003(17) 0.015(4) 0.0004(16)
C8A 0.012(4) 0.025(3) 0.026(5) 0.003(2) 0.010(4) -0.002(2)
C9A 0.024(3) 0.016(3) 0.033(3) -0.002(2) 0.016(3) -0.001(2)
C10A 0.016(3) 0.022(3) 0.029(3) -0.012(2) 0.007(2) 0.000(2)
C11A 0.027(3) 0.028(3) 0.025(4) -0.013(3) 0.012(3) -0.007(3)
C12A 0.026(3) 0.027(3) 0.023(3) 0.004(2) 0.012(3) -0.001(2)
C13A 0.021(3) 0.015(3) 0.027(3) -0.003(2) 0.012(3) -0.001(2)
O1 0.043(3) 0.040(2) 0.039(3) -0.009(2) 0.026(2) -0.018(2)
O2 0.032(3) 0.055(2) 0.042(3) 0.020(2) 0.024(2) 0.014(2)

_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
F10 C10 1.346(6) . ?
F12 C12 1.353(6) . ?
N1 C4 1.500(8) . ?
N1 C7 1.503(14) . ?
N1 C5 1.504(11) . ?
N1 C1 1.513(7) . ?
N2 C6 1.471(10) . ?
N2 C3 1.478(7) . ?
N2 C2 1.487(7) . ?
C1 C2 1.520(9) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.522(9) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.518(12) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.520(14) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C13 1.382(8) . ?
C8 C9 1.390(8) . ?
C9 C10 1.388(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.379(8) . ?
C11 C12 1.372(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.377(8) . ?
C13 H13 0.9500 . ?
N1A C4A 1.505(7) . ?
N1A C5A 1.511(7) . ?
N1A C1A 1.521(11) . ?
N1A C7A 1.536(13) . ?
N2A C3A 1.459(7) . ?
N2A C6A 1.461(7) . ?
N2A C2A 1.468(11) . ?
F10A C10A 1.354(5) . ?
F12A C12A 1.350(6) . ?
C1A C2A 1.558(11) . ?
C1A H1A1 0.9900 . ?
C1A H1A2 0.9900 . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C3A C4A 1.563(9) . ?
C3A H3A1 0.9900 . ?
C3A H3A2 0.9900 . ?
C4A H4A1 0.9900 . ?
C4A H4A2 0.9900 . ?
C5A C6A 1.550(9) . ?
C5A H5A1 0.9900 . ?
C5A H5A2 0.9900 . ?
C6A H6A1 0.9900 . ?
C6A H6A2 0.9900 . ?
C7A C8A 1.496(14) . ?
C7A H7A1 0.9900 . ?
C7A H7A2 0.9900 . ?
C8A C13A 1.401(8) . ?
C8A C9A 1.403(8) . ?
C9A C10A 1.367(8) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.385(8) . ?
C11A C12A 1.377(8) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.368(8) . ?
C13A H13A 0.9500 . ?
O1 H1O 0.82(2) . ?
O1 H1P 0.83(2) . ?
O2 H2O 0.84(2) . ?
O2 H2P 0.83(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
C4 N1 C7 112.2(5) . . ?
C4 N1 C5 108.8(5) . . ?
C7 N1 C5 107.6(6) . . ?
C4 N1 C1 108.4(6) . . ?
C7 N1 C1 111.3(5) . . ?
C5 N1 C1 108.4(5) . . ?
C6 N2 C3 108.5(5) . . ?
C6 N2 C2 108.4(5) . . ?
C3 N2 C2 107.5(5) . . ?
N1 C1 C2 108.9(5) . . ?
N1 C1 H1A 109.9 . . ?
C2 C1 H1A 109.9 . . ?
N1 C1 H1B 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
N2 C2 C1 112.0(5) . . ?
N2 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
N2 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
N2 C3 C4 111.9(5) . . ?
N2 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
N2 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
N1 C4 C3 109.3(5) . . ?
N1 C4 H4A 109.8 . . ?
C3 C4 H4A 109.8 . . ?
N1 C4 H4B 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?
N1 C5 C6 109.7(7) . . ?
N1 C5 H5A 109.7 . . ?
C6 C5 H5A 109.7 . . ?
N1 C5 H5B 109.7 . . ?
C6 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
N2 C6 C5 111.7(7) . . ?
N2 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
N2 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
N1 C7 C8 116.6(7) . . ?
N1 C7 H7A 108.1 . . ?
C8 C7 H7A 108.1 . . ?
N1 C7 H7B 108.1 . . ?
C8 C7 H7B 108.1 . . ?
H7A C7 H7B 107.3 . . ?
C13 C8 C9 120.1(8) . . ?
C13 C8 C7 119.5(5) . . ?
C9 C8 C7 120.3(5) . . ?
C10 C9 C8 118.4(6) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
F10 C10 C11 118.2(5) . . ?
F10 C10 C9 119.2(5) . . ?
C11 C10 C9 122.6(5) . . ?
C12 C11 C10 116.8(6) . . ?
C12 C11 H11 121.6 . . ?
C10 C11 H11 121.6 . . ?
F12 C12 C11 118.1(5) . . ?
F12 C12 C13 119.0(4) . . ?
C11 C12 C13 122.9(5) . . ?
C12 C13 C8 119.0(5) . . ?
C12 C13 H13 120.5 . . ?
C8 C13 H13 120.5 . . ?
C4A N1A C5A 110.2(6) . . ?
C4A N1A C1A 108.9(5) . . ?
C5A N1A C1A 108.4(5) . . ?
C4A N1A C7A 111.4(5) . . ?
C5A N1A C7A 111.4(5) . . ?
C1A N1A C7A 106.3(6) . . ?
C3A N2A C6A 109.5(6) . . ?
C3A N2A C2A 108.8(5) . . ?
C6A N2A C2A 108.9(5) . . ?
N1A C1A C2A 108.2(7) . . ?
N1A C1A H1A1 110.1 . . ?
C2A C1A H1A1 110.1 . . ?
N1A C1A H1A2 110.1 . . ?
C2A C1A H1A2 110.1 . . ?
H1A1 C1A H1A2 108.4 . . ?
N2A C2A C1A 111.1(7) . . ?
N2A C2A H2A1 109.4 . . ?
C1A C2A H2A1 109.4 . . ?
N2A C2A H2A2 109.4 . . ?
C1A C2A H2A2 109.4 . . ?
H2A1 C2A H2A2 108.0 . . ?
N2A C3A C4A 111.9(5) . . ?
N2A C3A H3A1 109.2 . . ?
C4A C3A H3A1 109.2 . . ?
N2A C3A H3A2 109.2 . . ?
C4A C3A H3A2 109.2 . . ?
H3A1 C3A H3A2 107.9 . . ?
N1A C4A C3A 107.5(5) . . ?
N1A C4A H4A1 110.2 . . ?
C3A C4A H4A1 110.2 . . ?
N1A C4A H4A2 110.2 . . ?
C3A C4A H4A2 110.2 . . ?
H4A1 C4A H4A2 108.5 . . ?
N1A C5A C6A 108.2(5) . . ?
N1A C5A H5A1 110.1 . . ?
C6A C5A H5A1 110.1 . . ?
N1A C5A H5A2 110.1 . . ?
C6A C5A H5A2 110.1 . . ?
H5A1 C5A H5A2 108.4 . . ?
N2A C6A C5A 111.7(5) . . ?
N2A C6A H6A1 109.3 . . ?
C5A C6A H6A1 109.3 . . ?
N2A C6A H6A2 109.3 . . ?
C5A C6A H6A2 109.3 . . ?
H6A1 C6A H6A2 107.9 . . ?
C8A C7A N1A 113.6(7) . . ?
C8A C7A H7A1 108.8 . . ?
N1A C7A H7A1 108.8 . . ?
C8A C7A H7A2 108.8 . . ?
N1A C7A H7A2 108.8 . . ?
H7A1 C7A H7A2 107.7 . . ?
C13A C8A C9A 119.9(7) . . ?
C13A C8A C7A 120.9(5) . . ?
C9A C8A C7A 118.9(6) . . ?
C10A C9A C8A 118.0(6) . . ?
C10A C9A H9A 121.0 . . ?
C8A C9A H9A 121.0 . . ?
F10A C10A C9A 118.6(4) . . ?
F10A C10A C11A 117.2(5) . . ?
C9A C10A C11A 124.2(5) . . ?
C12A C11A C10A 115.5(6) . . ?
C12A C11A H11A 122.2 . . ?
C10A C11A H11A 122.2 . . ?
F12A C12A C13A 119.0(5) . . ?
F12A C12A C11A 116.9(5) . . ?
C13A C12A C11A 124.1(5) . . ?
C12A C13A C8A 118.3(5) . . ?
C12A C13A H13A 120.9 . . ?
C8A C13A H13A 120.9 . . ?
H1O O1 H1P 116(7) . . ?
H2O O2 H2P 105(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 -58.8(8) . . . . ?
C7 N1 C1 C2 177.4(6) . . . . ?
C5 N1 C1 C2 59.2(7) . . . . ?
C6 N2 C2 C1 -57.9(7) . . . . ?
C3 N2 C2 C1 59.2(7) . . . . ?
N1 C1 C2 N2 -0.9(7) . . . . ?
C6 N2 C3 C4 58.7(7) . . . . ?
C2 N2 C3 C4 -58.3(7) . . . . ?
C7 N1 C4 C3 -177.0(6) . . . . ?
C5 N1 C4 C3 -58.0(7) . . . . ?
C1 N1 C4 C3 59.7(8) . . . . ?
N2 C3 C4 N1 -0.6(7) . . . . ?
C4 N1 C5 C6 58.7(6) . . . . ?
C7 N1 C5 C6 -179.4(4) . . . . ?
C1 N1 C5 C6 -59.0(6) . . . . ?
C3 N2 C6 C5 -58.1(6) . . . . ?
C2 N2 C6 C5 58.4(6) . . . . ?
N1 C5 C6 N2 -0.3(6) . . . . ?
C4 N1 C7 C8 -55.2(6) . . . . ?
C5 N1 C7 C8 -174.9(4) . . . . ?
C1 N1 C7 C8 66.5(6) . . . . ?
N1 C7 C8 C13 95.4(8) . . . . ?
N1 C7 C8 C9 -85.5(7) . . . . ?
C13 C8 C9 C10 0.9(10) . . . . ?
C7 C8 C9 C10 -178.3(7) . . . . ?
C8 C9 C10 F10 -179.6(6) . . . . ?
C8 C9 C10 C11 1.6(9) . . . . ?
F10 C10 C11 C12 178.4(5) . . . . ?
C9 C10 C11 C12 -2.8(8) . . . . ?
C10 C11 C12 F12 -179.0(5) . . . . ?
C10 C11 C12 C13 1.5(8) . . . . ?
F12 C12 C13 C8 -178.6(6) . . . . ?
C11 C12 C13 C8 0.9(9) . . . . ?
C9 C8 C13 C12 -2.1(10) . . . . ?
C7 C8 C13 C12 177.0(7) . . . . ?
C4A N1A C1A C2A -58.0(6) . . . . ?
C5A N1A C1A C2A 61.9(6) . . . . ?
C7A N1A C1A C2A -178.2(3) . . . . ?
C3A N2A C2A C1A 61.8(6) . . . . ?
C6A N2A C2A C1A -57.5(6) . . . . ?
N1A C1A C2A N2A -3.8(5) . . . . ?
C6A N2A C3A C4A 61.2(8) . . . . ?
C2A N2A C3A C4A -57.7(7) . . . . ?
C5A N1A C4A C3A -56.8(8) . . . . ?
C1A N1A C4A C3A 62.0(7) . . . . ?
C7A N1A C4A C3A 178.9(6) . . . . ?
N2A C3A C4A N1A -3.8(7) . . . . ?
C4A N1A C5A C6A 61.1(8) . . . . ?
C1A N1A C5A C6A -58.0(7) . . . . ?
C7A N1A C5A C6A -174.6(6) . . . . ?
C3A N2A C6A C5A -56.9(8) . . . . ?
C2A N2A C6A C5A 61.9(7) . . . . ?
N1A C5A C6A N2A -3.2(7) . . . . ?
C4A N1A C7A C8A 59.0(6) . . . . ?
C5A N1A C7A C8A -64.6(6) . . . . ?
C1A N1A C7A C8A 177.5(4) . . . . ?
N1A C7A C8A C13A 85.7(8) . . . . ?
N1A C7A C8A C9A -100.6(7) . . . . ?
C13A C8A C9A C10A -0.7(11) . . . . ?
C7A C8A C9A C10A -174.5(7) . . . . ?
C8A C9A C10A F10A 179.9(6) . . . . ?
C8A C9A C10A C11A 1.3(9) . . . . ?
F10A C10A C11A C12A 180.0(4) . . . . ?
C9A C10A C11A C12A -1.4(8) . . . . ?
C10A C11A C12A F12A -178.0(5) . . . . ?
C10A C11A C12A C13A 0.9(8) . . . . ?
F12A C12A C13A C8A 178.5(6) . . . . ?
C11A C12A C13A C8A -0.5(9) . . . . ?
C9A C8A C13A C12A 0.3(11) . . . . ?
C7A C8A C13A C12A 174.0(7) . . . . ?

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
O1 H1O Br1 0.82(2) 2.61(4) 3.350(4) 150(7) .
O1 H1P N2 0.83(2) 2.11(3) 2.908(7) 160(6) .
O2 H2O N2A 0.84(2) 2.23(5) 2.894(8) 137(6) .
O2 H2O F10 0.84(2) 2.50(5) 3.159(5) 136(5) 3_676
O2 H2P Br2 0.83(2) 2.61(5) 3.362(5) 151(8) .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.074