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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_12DBrTFB-NMA
#TrackingRef 'CIFs.cif'

#===============================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1,2-Dibromotetrafluorobenzene N-Methylacetamide
;
_chemical_name_common            ?
_chemical_melting_point          302(2)
_chemical_formula_moiety         '(C6 Br2 F4), (C3 H7 N O)'
_chemical_formula_sum            'C9 H7 Br2 F4 N O'
_chemical_formula_weight         380.98

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_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14


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                   7.5319(13)
_cell_length_b                   20.560(3)
_cell_length_c                   8.9505(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.813(8)
_cell_angle_gamma                90.00
_cell_volume                     1258.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    320
_cell_measurement_theta_min      0.98
_cell_measurement_theta_max      27.89

_exptl_crystal_description       Capillary
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.011
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    6.475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2468
_exptl_absorpt_correction_T_max  0.2468
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12208
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_av_sigmaI/netI    0.0764
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2451
_reflns_number_gt                1416
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0776P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2451
_refine_ls_number_parameters     165
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1389
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_restrained_S_all      0.958
_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
N1A N 0.3613(17) 0.2230(5) 0.1240(12) 0.062(3) Uani 0.540(8) 1 d PD A -1
H1A H 0.3738 0.2485 0.0515 0.075 Uiso 0.540(8) 1 calc PR A -1
C9A C 0.251(3) 0.1660(7) 0.075(3) 0.068(3) Uani 0.540(8) 1 d PD A -1
H9A1 H 0.3376 0.1288 0.1006 0.102 Uiso 0.540(8) 1 calc PR A -1
H9A2 H 0.1703 0.1675 -0.0426 0.102 Uiso 0.540(8) 1 calc PR A -1
H9A3 H 0.1675 0.1623 0.1329 0.102 Uiso 0.540(8) 1 calc PR A -1
O1A O 0.4107(9) 0.2008(3) 0.3823(6) 0.0795(17) Uani 0.540(8) 1 d PD A -1
C7A C 0.449(2) 0.2380(7) 0.2866(13) 0.057(3) Uani 0.540(8) 1 d PD A -1
C8A C 0.587(9) 0.297(3) 0.342(4) 0.068(3) Uani 0.540(8) 1 d PD A -1
H8A1 H 0.5159 0.3349 0.3538 0.102 Uiso 0.540(8) 1 calc PR A -1
H8A2 H 0.6375 0.3065 0.2609 0.102 Uiso 0.540(8) 1 calc PR A -1
H8A3 H 0.6954 0.2880 0.4473 0.102 Uiso 0.540(8) 1 calc PR A -1
O1B O 0.4107(9) 0.2008(3) 0.3823(6) 0.0795(17) Uani 0.460(8) 1 d PD A -2
N1B N 0.461(2) 0.2592(6) 0.2057(19) 0.062(3) Uani 0.460(8) 1 d PD A -2
H1B H 0.4371 0.2674 0.1036 0.075 Uiso 0.460(8) 1 calc PR A -2
C7B C 0.363(2) 0.2092(7) 0.2363(17) 0.057(3) Uani 0.460(8) 1 d PD A -2
C8B C 0.197(3) 0.1823(9) 0.072(3) 0.068(3) Uani 0.460(8) 1 d PD A -2
H8B1 H 0.2001 0.1351 0.0733 0.102 Uiso 0.460(8) 1 calc PR A -2
H8B2 H 0.2184 0.1980 -0.0216 0.102 Uiso 0.460(8) 1 calc PR A -2
H8B3 H 0.0707 0.1971 0.0626 0.102 Uiso 0.460(8) 1 calc PR A -2
C9B C 0.596(10) 0.298(3) 0.326(5) 0.068(3) Uani 0.460(8) 1 d PD A -2
H9B1 H 0.5405 0.3139 0.3989 0.102 Uiso 0.460(8) 1 calc PR A -2
H9B2 H 0.6306 0.3345 0.2747 0.102 Uiso 0.460(8) 1 calc PR A -2
H9B3 H 0.7126 0.2726 0.3887 0.102 Uiso 0.460(8) 1 calc PR A -2
Br1 Br 0.30859(9) 0.42029(4) -0.03367(9) 0.0533(3) Uani 1 1 d . . .
Br2 Br 0.13505(12) 0.54410(4) -0.30245(9) 0.0638(3) Uani 1 1 d . . .
C1 C 0.2518(8) 0.5022(3) 0.0287(8) 0.0435(16) Uani 1 1 d . . .
C2 C 0.1787(9) 0.5533(3) -0.0799(8) 0.0425(16) Uani 1 1 d . . .
C3 C 0.1427(10) 0.6120(4) -0.0265(10) 0.0556(18) Uani 1 1 d . . .
C4 C 0.1757(10) 0.6205(4) 0.1377(10) 0.059(2) Uani 1 1 d . . .
C5 C 0.2442(11) 0.5704(4) 0.2430(9) 0.058(2) Uani 1 1 d . . .
C6 C 0.2833(9) 0.5119(4) 0.1916(8) 0.0506(18) Uani 1 1 d . . .
F1 F 0.3509(6) 0.4637(2) 0.3025(5) 0.0710(13) Uani 1 1 d . . .
F2 F 0.0725(7) 0.6616(2) -0.1313(6) 0.0749(13) Uani 1 1 d . . .
F3 F 0.1341(7) 0.6776(2) 0.1859(6) 0.0820(14) Uani 1 1 d . . .
F4 F 0.2743(7) 0.5787(2) 0.4011(5) 0.0846(15) 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
N1A 0.075(7) 0.064(7) 0.049(6) 0.001(5) 0.027(6) -0.015(5)
C9A 0.081(6) 0.065(5) 0.059(4) -0.015(5) 0.031(5) -0.015(4)
O1A 0.128(5) 0.074(4) 0.045(3) 0.008(3) 0.044(3) -0.008(4)
C7A 0.069(10) 0.055(10) 0.039(7) -0.008(6) 0.016(7) 0.005(6)
C8A 0.081(6) 0.065(5) 0.059(4) -0.015(5) 0.031(5) -0.015(4)
O1B 0.128(5) 0.074(4) 0.045(3) 0.008(3) 0.044(3) -0.008(4)
N1B 0.075(7) 0.064(7) 0.049(6) 0.001(5) 0.027(6) -0.015(5)
C7B 0.069(10) 0.055(10) 0.039(7) -0.008(6) 0.016(7) 0.005(6)
C8B 0.081(6) 0.065(5) 0.059(4) -0.015(5) 0.031(5) -0.015(4)
C9B 0.081(6) 0.065(5) 0.059(4) -0.015(5) 0.031(5) -0.015(4)
Br1 0.0390(4) 0.0671(5) 0.0580(5) -0.0010(4) 0.0245(3) -0.0022(3)
Br2 0.0713(5) 0.0830(6) 0.0388(4) 0.0017(4) 0.0250(4) -0.0090(4)
C1 0.032(3) 0.060(5) 0.042(4) 0.000(3) 0.020(3) -0.014(3)
C2 0.032(3) 0.060(4) 0.039(4) -0.001(3) 0.018(3) -0.013(3)
C3 0.042(4) 0.063(5) 0.060(5) 0.001(4) 0.019(3) -0.011(4)
C4 0.045(4) 0.071(6) 0.063(5) -0.021(5) 0.023(4) -0.017(4)
C5 0.056(5) 0.085(6) 0.040(4) -0.015(4) 0.026(4) -0.022(4)
C6 0.034(3) 0.075(5) 0.040(4) 0.007(4) 0.013(3) -0.010(3)
F1 0.066(3) 0.098(4) 0.045(2) 0.017(2) 0.020(2) 0.006(2)
F2 0.088(3) 0.065(3) 0.074(3) 0.010(2) 0.035(3) -0.001(2)
F3 0.100(4) 0.073(3) 0.087(3) -0.025(3) 0.053(3) -0.017(3)
F4 0.089(3) 0.120(4) 0.046(3) -0.022(3) 0.030(2) -0.023(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
N1A C7A 1.357(9) . ?
N1A C9A 1.398(9) . ?
N1A H1A 0.8700 . ?
C9A H9A1 0.9700 . ?
C9A H9A2 0.9700 . ?
C9A H9A3 0.9700 . ?
O1A C7A 1.269(13) . ?
C7A C8A 1.545(17) . ?
C8A H8A1 0.9700 . ?
C8A H8A2 0.9700 . ?
C8A H8A3 0.9700 . ?
N1B C7B 1.358(9) . ?
N1B C9B 1.382(10) . ?
N1B H1B 0.8700 . ?
C7B C8B 1.580(17) . ?
C8B H8B1 0.9700 . ?
C8B H8B2 0.9700 . ?
C8B H8B3 0.9700 . ?
C9B H9B1 0.9700 . ?
C9B H9B2 0.9700 . ?
C9B H9B3 0.9700 . ?
Br1 C1 1.878(7) . ?
Br2 C2 1.887(6) . ?
C1 C2 1.380(9) . ?
C1 C6 1.390(9) . ?
C2 C3 1.366(10) . ?
C3 F2 1.336(8) . ?
C3 C4 1.395(11) . ?
C4 F3 1.332(9) . ?
C4 C5 1.345(11) . ?
C5 F4 1.346(8) . ?
C5 C6 1.364(10) . ?
C6 F1 1.342(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7A N1A C9A 119.0(15) . . ?
C7A N1A H1A 120.5 . . ?
C9A N1A H1A 120.5 . . ?
O1A C7A N1A 116.2(11) . . ?
O1A C7A C8A 124.9(16) . . ?
N1A C7A C8A 118.9(16) . . ?
C7B N1B C9B 124(2) . . ?
C7B N1B H1B 117.8 . . ?
C9B N1B H1B 117.8 . . ?
N1B C7B C8B 111.2(15) . . ?
C7B C8B H8B1 109.5 . . ?
C7B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
C7B C8B H8B3 109.5 . . ?
H8B1 C8B H8B3 109.5 . . ?
H8B2 C8B H8B3 109.5 . . ?
N1B C9B H9B1 109.5 . . ?
N1B C9B H9B2 109.5 . . ?
H9B1 C9B H9B2 109.5 . . ?
N1B C9B H9B3 109.5 . . ?
H9B1 C9B H9B3 109.5 . . ?
H9B2 C9B H9B3 109.5 . . ?
C2 C1 C6 118.1(7) . . ?
C2 C1 Br1 123.2(5) . . ?
C6 C1 Br1 118.7(5) . . ?
C3 C2 C1 120.4(7) . . ?
C3 C2 Br2 119.0(5) . . ?
C1 C2 Br2 120.6(5) . . ?
F2 C3 C2 120.5(7) . . ?
F2 C3 C4 119.1(7) . . ?
C2 C3 C4 120.4(7) . . ?
F3 C4 C5 121.4(7) . . ?
F3 C4 C3 119.4(8) . . ?
C5 C4 C3 119.2(8) . . ?
C4 C5 F4 119.1(8) . . ?
C4 C5 C6 120.9(7) . . ?
F4 C5 C6 120.1(7) . . ?
F1 C6 C5 118.0(6) . . ?
F1 C6 C1 121.0(7) . . ?
C5 C6 C1 121.0(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
C9A N1A C7A O1A -5(2) . . . . ?
C9A N1A C7A C8A 174(3) . . . . ?
C9B N1B C7B C8B 171(4) . . . . ?
C6 C1 C2 C3 1.3(9) . . . . ?
Br1 C1 C2 C3 -179.2(5) . . . . ?
C6 C1 C2 Br2 179.3(4) . . . . ?
Br1 C1 C2 Br2 -1.2(7) . . . . ?
C1 C2 C3 F2 179.8(6) . . . . ?
Br2 C2 C3 F2 1.8(8) . . . . ?
C1 C2 C3 C4 -1.3(9) . . . . ?
Br2 C2 C3 C4 -179.2(5) . . . . ?
F2 C3 C4 F3 0.9(10) . . . . ?
C2 C3 C4 F3 -178.1(6) . . . . ?
F2 C3 C4 C5 179.3(6) . . . . ?
C2 C3 C4 C5 0.3(10) . . . . ?
F3 C4 C5 F4 -1.1(11) . . . . ?
C3 C4 C5 F4 -179.4(6) . . . . ?
F3 C4 C5 C6 179.0(6) . . . . ?
C3 C4 C5 C6 0.6(11) . . . . ?
C4 C5 C6 F1 -179.8(6) . . . . ?
F4 C5 C6 F1 0.2(10) . . . . ?
C4 C5 C6 C1 -0.6(10) . . . . ?
F4 C5 C6 C1 179.5(6) . . . . ?
C2 C1 C6 F1 178.8(5) . . . . ?
Br1 C1 C6 F1 -0.7(8) . . . . ?
C2 C1 C6 C5 -0.4(9) . . . . ?
Br1 C1 C6 C5 -179.9(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.640
_refine_diff_density_min         -1.153
_refine_diff_density_rms         0.232
_database_code_depnum_ccdc_archive 'CCDC 899779'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_13DBrTFB-NMA
#TrackingRef 'CIFs.cif'

#===============================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1,3-Dibromotetrafluorobenzene N-Methylacetamide
;
_chemical_name_common            ?
_chemical_melting_point          306(2)
_chemical_formula_moiety         '(C6 Br2 F4), (C3 H7 N O)'
_chemical_formula_sum            'C9 H7 Br2 F4 N O'
_chemical_formula_weight         380.98

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_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

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                   7.7932(6)
_cell_length_b                   19.6616(14)
_cell_length_c                   8.8023(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.553(4)
_cell_angle_gamma                90.00
_cell_volume                     1216.82(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    350
_cell_measurement_theta_min      0.98
_cell_measurement_theta_max      27.78

_exptl_crystal_description       Capillary
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.080
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    6.695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2386
_exptl_absorpt_correction_T_max  0.3478
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11226
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.77
_diffrn_reflns_theta_max         26.43
_reflns_number_total             2487
_reflns_number_gt                1972
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0182P)²+1.1260P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2487
_refine_ls_number_parameters     174
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_ref         0.0587
_refine_ls_wR_factor_gt          0.0538
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.055
_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
O1 O 0.586(3) -0.1946(16) 1.186(2) 0.031(3) Uani 0.631(4) 1 d PD A 1
N1 N 0.7693(12) -0.2265(4) 1.4507(10) 0.0301(10) Uani 0.369(4) 1 d PD A 1
H1 H 0.8706 -0.2484 1.5219 0.036 Uiso 0.369(4) 1 calc PR A 1
C7 C 0.7100(15) -0.2365(5) 1.2836(11) 0.0253(12) Uani 0.369(4) 1 d PD A 1
C8 C 0.800(3) -0.2934(10) 1.221(2) 0.032(2) Uani 0.631(4) 1 d PD A 1
H8A H 0.7208 -0.3344 1.1976 0.048 Uiso 0.631(4) 1 calc PR A 1
H8B H 0.9276 -0.3035 1.3084 0.048 Uiso 0.631(4) 1 calc PR A 1
H8C H 0.8079 -0.2785 1.1184 0.048 Uiso 0.631(4) 1 calc PR A 1
C9 C 0.676(6) -0.1831(16) 1.513(5) 0.036(3) Uani 0.369(4) 1 d PD A 1
H9A H 0.7003 -0.1359 1.4920 0.054 Uiso 0.369(4) 1 calc PR A 1
H9B H 0.7220 -0.1904 1.6343 0.054 Uiso 0.369(4) 1 calc PR A 1
H9C H 0.5388 -0.1921 1.4565 0.054 Uiso 0.369(4) 1 calc PR A 1
C7A C 0.6817(8) -0.2090(3) 1.3390(8) 0.0253(12) Uani 0.631(4) 1 d PD A 2
C8A C 0.691(3) -0.1716(8) 1.495(3) 0.036(3) Uani 0.631(4) 1 d PD A 2
H8A1 H 0.7290 -0.1242 1.4931 0.054 Uiso 0.631(4) 1 calc PR A 2
H8A2 H 0.7842 -0.1939 1.5971 0.054 Uiso 0.631(4) 1 calc PR A 2
H8A3 H 0.5655 -0.1727 1.4961 0.054 Uiso 0.631(4) 1 calc PR A 2
N1A N 0.8052(7) -0.2594(2) 1.3646(6) 0.0301(10) Uani 0.631(4) 1 d PD A 2
H1A H 0.8821 -0.2691 1.4698 0.036 Uiso 0.631(4) 1 calc PR A 2
O1A O 0.557(5) -0.191(3) 1.199(4) 0.031(3) Uani 0.369(4) 1 d PD A 2
C9A C 0.824(6) -0.2980(18) 1.241(4) 0.032(2) Uani 0.369(4) 1 d PD A 2
H9A1 H 0.7075 -0.2940 1.1356 0.048 Uiso 0.369(4) 1 calc PR A 2
H9A2 H 0.8438 -0.3458 1.2761 0.048 Uiso 0.369(4) 1 calc PR A 2
H9A3 H 0.9324 -0.2816 1.2233 0.048 Uiso 0.369(4) 1 calc PR A 2
Br1 Br 0.37596(5) -0.071312(17) 1.08329(4) 0.02340(10) Uani 1 1 d . . .
Br2 Br -0.25257(5) 0.035841(19) 0.51750(4) 0.03041(11) Uani 1 1 d . . .
C1 C 0.2180(4) 0.00255(17) 0.9733(4) 0.0198(7) Uani 1 1 d . . .
C2 C 0.0702(5) -0.00479(16) 0.8141(4) 0.0215(7) Uani 1 1 d . . .
C3 C -0.0470(5) 0.04884(17) 0.7298(4) 0.0211(7) Uani 1 1 d . . .
C4 C -0.0134(5) 0.11137(17) 0.8068(4) 0.0242(8) Uani 1 1 d . . .
C5 C 0.1304(5) 0.11983(17) 0.9667(4) 0.0250(8) Uani 1 1 d . . .
C6 C 0.2440(5) 0.06560(17) 1.0469(4) 0.0223(7) Uani 1 1 d . . .
F1 F 0.0354(3) -0.06655(9) 0.7422(2) 0.0273(4) Uani 1 1 d . . .
F2 F -0.1242(3) 0.16462(9) 0.7300(2) 0.0339(5) Uani 1 1 d . . .
F3 F 0.1574(3) 0.18056(10) 1.0434(2) 0.0364(5) Uani 1 1 d . . .
F4 F 0.3836(3) 0.07547(10) 1.2033(2) 0.0305(5) 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
O1 0.026(6) 0.032(3) 0.023(3) 0.004(3) -0.001(3) 0.006(4)
N1 0.027(3) 0.029(3) 0.025(3) 0.0025(19) 0.003(2) 0.006(2)
C7 0.022(3) 0.020(3) 0.030(4) -0.005(2) 0.008(2) -0.005(2)
C8 0.033(6) 0.029(3) 0.030(4) 0.005(3) 0.011(5) 0.009(3)
C9 0.047(4) 0.025(6) 0.030(5) -0.002(5) 0.011(3) 0.004(4)
C7A 0.022(3) 0.020(3) 0.030(4) -0.005(2) 0.008(2) -0.005(2)
C8A 0.047(4) 0.025(6) 0.030(5) -0.002(5) 0.011(3) 0.004(4)
N1A 0.027(3) 0.029(3) 0.025(3) 0.0025(19) 0.003(2) 0.006(2)
O1A 0.026(6) 0.032(3) 0.023(3) 0.004(3) -0.001(3) 0.006(4)
C9A 0.033(6) 0.029(3) 0.030(4) 0.005(3) 0.011(5) 0.009(3)
Br1 0.01846(18) 0.02825(18) 0.02289(18) 0.00552(15) 0.00834(14) 0.00323(15)
Br2 0.0233(2) 0.0410(2) 0.01950(19) 0.00584(16) 0.00227(15) -0.00155(17)
C1 0.0148(17) 0.0280(18) 0.0191(17) 0.0077(14) 0.0096(14) 0.0007(14)
C2 0.0206(18) 0.0246(17) 0.0223(18) -0.0013(15) 0.0122(14) -0.0033(15)
C3 0.0146(18) 0.0306(18) 0.0158(16) 0.0045(14) 0.0046(14) 0.0001(14)
C4 0.023(2) 0.0254(18) 0.0253(18) 0.0111(16) 0.0117(16) 0.0055(16)
C5 0.026(2) 0.0234(18) 0.0278(19) 0.0003(15) 0.0142(16) -0.0047(16)
C6 0.0174(18) 0.0287(18) 0.0196(17) 0.0013(15) 0.0070(14) -0.0063(15)
F1 0.0269(11) 0.0276(11) 0.0241(11) -0.0033(9) 0.0079(9) 0.0010(9)
F2 0.0322(12) 0.0270(11) 0.0366(12) 0.0122(9) 0.0092(10) 0.0047(9)
F3 0.0442(14) 0.0234(10) 0.0352(12) -0.0021(9) 0.0110(10) -0.0039(10)
F4 0.0266(12) 0.0329(11) 0.0219(10) -0.0007(9) 0.0008(9) -0.0041(10)

_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
O1 C7 1.279(15) . ?
N1 C7 1.352(8) . ?
N1 C9 1.380(10) . ?
N1 H1 0.8800 . ?
C7 C8 1.540(13) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C7A O1A 1.244(19) . ?
C7A N1A 1.331(6) . ?
C7A C8A 1.536(14) . ?
C8A H8A1 0.9800 . ?
C8A H8A2 0.9800 . ?
C8A H8A3 0.9800 . ?
N1A C9A 1.385(10) . ?
N1A H1A 0.8800 . ?
C9A H9A1 0.9800 . ?
C9A H9A2 0.9800 . ?
C9A H9A3 0.9800 . ?
Br1 C1 1.880(3) . ?
Br2 C3 1.882(3) . ?
C1 C6 1.373(5) . ?
C1 C2 1.385(4) . ?
C2 F1 1.342(4) . ?
C2 C3 1.382(4) . ?
C3 C4 1.374(5) . ?
C4 F2 1.340(4) . ?
C4 C5 1.380(5) . ?
C5 F3 1.343(4) . ?
C5 C6 1.371(5) . ?
C6 F4 1.351(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C9 122(2) . . ?
C7 N1 H1 119.0 . . ?
C9 N1 H1 119.0 . . ?
O1 C7 N1 116.3(13) . . ?
O1 C7 C8 123.8(14) . . ?
N1 C7 C8 119.8(10) . . ?
O1A C7A N1A 125(2) . . ?
O1A C7A C8A 118(2) . . ?
N1A C7A C8A 117.0(10) . . ?
C7A C8A H8A1 109.5 . . ?
C7A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
C7A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
C7A N1A C9A 126.0(17) . . ?
C7A N1A H1A 117.0 . . ?
C9A N1A H1A 117.0 . . ?
N1A C9A H9A1 109.5 . . ?
N1A C9A H9A2 109.5 . . ?
H9A1 C9A H9A2 109.5 . . ?
N1A C9A H9A3 109.5 . . ?
H9A1 C9A H9A3 109.5 . . ?
H9A2 C9A H9A3 109.5 . . ?
C6 C1 C2 117.4(3) . . ?
C6 C1 Br1 121.6(3) . . ?
C2 C1 Br1 121.0(3) . . ?
F1 C2 C3 119.0(3) . . ?
F1 C2 C1 118.8(3) . . ?
C3 C2 C1 122.2(3) . . ?
C4 C3 C2 118.5(3) . . ?
C4 C3 Br2 120.7(2) . . ?
C2 C3 Br2 120.8(3) . . ?
F2 C4 C3 120.4(3) . . ?
F2 C4 C5 118.9(3) . . ?
C3 C4 C5 120.6(3) . . ?
F3 C5 C6 120.5(3) . . ?
F3 C5 C4 120.1(3) . . ?
C6 C5 C4 119.4(3) . . ?
F4 C6 C5 118.0(3) . . ?
F4 C6 C1 120.0(3) . . ?
C5 C6 C1 121.9(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
C9 N1 C7 O1 13(3) . . . . ?
C9 N1 C7 C8 -171(2) . . . . ?
O1A C7A N1A C9A 4(4) . . . . ?
C8A C7A N1A C9A -178(2) . . . . ?
C6 C1 C2 F1 -176.8(3) . . . . ?
Br1 C1 C2 F1 3.1(4) . . . . ?
C6 C1 C2 C3 0.7(5) . . . . ?
Br1 C1 C2 C3 -179.4(2) . . . . ?
F1 C2 C3 C4 178.1(3) . . . . ?
C1 C2 C3 C4 0.6(5) . . . . ?
F1 C2 C3 Br2 0.1(4) . . . . ?
C1 C2 C3 Br2 -177.4(2) . . . . ?
C2 C3 C4 F2 -179.6(3) . . . . ?
Br2 C3 C4 F2 -1.6(4) . . . . ?
C2 C3 C4 C5 -1.9(5) . . . . ?
Br2 C3 C4 C5 176.1(2) . . . . ?
F2 C4 C5 F3 0.2(5) . . . . ?
C3 C4 C5 F3 -177.5(3) . . . . ?
F2 C4 C5 C6 179.6(3) . . . . ?
C3 C4 C5 C6 1.9(5) . . . . ?
F3 C5 C6 F4 -0.6(5) . . . . ?
C4 C5 C6 F4 180.0(3) . . . . ?
F3 C5 C6 C1 178.8(3) . . . . ?
C4 C5 C6 C1 -0.6(5) . . . . ?
C2 C1 C6 F4 178.7(3) . . . . ?
Br1 C1 C6 F4 -1.2(4) . . . . ?
C2 C1 C6 C5 -0.7(5) . . . . ?
Br1 C1 C6 C5 179.4(2) . . . . ?


_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.43
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.094
_database_code_depnum_ccdc_archive 'CCDC 899780'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_14DBrTFB-NMA
#TrackingRef 'CIFs.cif'

#===============================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1,4-Dibromotetrafluorobenzene N-Methylacetamide
;
_chemical_name_common            ?
_chemical_melting_point          345(2)
_chemical_formula_moiety         '(C6 Br2 F4), (C3 H7 N O)'
_chemical_formula_sum            'C9 H7 Br2 F4 N O'
_chemical_formula_weight         380.98

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_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

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                   5.8653(3)
_cell_length_b                   9.0752(5)
_cell_length_c                   22.3773(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.126(3)
_cell_angle_gamma                90.00
_cell_volume                     1186.35(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    290
_cell_measurement_theta_min      0.97
_cell_measurement_theta_max      27.87

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.133
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    6.867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2895
_exptl_absorpt_correction_T_max  0.3553
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23328
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_sigmaI/netI    0.0221
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2323
_reflns_number_gt                1996


_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0624P)²+2.0144P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2323
_refine_ls_number_parameters     168
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.1103
_refine_ls_wR_factor_gt          0.0955
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_restrained_S_all      1.177
_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
C8A C 0.686(4) 0.397(3) 0.6932(12) 0.029(2) Uani 0.440(5) 1 d PD A 1
H8A1 H 0.6257 0.4042 0.6515 0.043 Uiso 0.440(5) 1 calc PR A 1
H8A2 H 0.7553 0.3012 0.7006 0.043 Uiso 0.440(5) 1 calc PR A 1
H8A3 H 0.8013 0.4732 0.7017 0.043 Uiso 0.440(5) 1 calc PR A 1
N1A N 0.4487(14) 0.3103(9) 0.7723(3) 0.0226(11) Uani 0.440(5) 1 d PD A 1
H1A H 0.5427 0.2374 0.7806 0.027 Uiso 0.440(5) 1 calc PR A 1
C7A C 0.492(2) 0.4188(11) 0.7337(4) 0.0233(16) Uani 0.440(5) 1 d PD A 1
O1A O 0.391(5) 0.537(3) 0.731(2) 0.027(3) Uani 0.440(5) 1 d PD A 1
C9A C 0.244(3) 0.323(3) 0.7977(9) 0.029(2) Uani 0.440(5) 1 d PD A 1
H9A1 H 0.1894 0.4240 0.7934 0.043 Uiso 0.440(5) 1 calc PR A 1
H9A2 H 0.2668 0.2984 0.8400 0.043 Uiso 0.440(5) 1 calc PR A 1
H9A3 H 0.1323 0.2571 0.7777 0.043 Uiso 0.440(5) 1 calc PR A 1
O1B O 0.335(3) 0.527(2) 0.7340(18) 0.027(3) Uani 0.560(5) 1 d PD A 2
C7B C 0.4010(14) 0.4070(9) 0.7548(4) 0.0233(16) Uani 0.560(5) 1 d PD A 2
N1B N 0.5877(10) 0.3366(7) 0.7378(3) 0.0226(11) Uani 0.560(5) 1 d PD A 2
H1B H 0.6185 0.2500 0.7531 0.027 Uiso 0.560(5) 1 calc PR A 2
C8B C 0.285(2) 0.327(2) 0.8076(6) 0.029(2) Uani 0.560(5) 1 d PD A 2
H8B1 H 0.3239 0.3788 0.8449 0.043 Uiso 0.560(5) 1 calc PR A 2
H8B2 H 0.3410 0.2261 0.8113 0.043 Uiso 0.560(5) 1 calc PR A 2
H8B3 H 0.1204 0.3259 0.7986 0.043 Uiso 0.560(5) 1 calc PR A 2
C9B C 0.734(3) 0.392(2) 0.6979(9) 0.029(2) Uani 0.560(5) 1 d PD A 2
H9B1 H 0.6451 0.4412 0.6651 0.043 Uiso 0.560(5) 1 calc PR A 2
H9B2 H 0.8197 0.3115 0.6821 0.043 Uiso 0.560(5) 1 calc PR A 2
H9B3 H 0.8390 0.4615 0.7184 0.043 Uiso 0.560(5) 1 calc PR A 2
Br1 Br 1.17610(8) 0.87628(5) 1.115834(19) 0.02459(17) Uani 1 1 d . . .
Br2 Br 0.77630(8) 0.59530(5) 0.85829(2) 0.03069(18) Uani 1 1 d . . .
C1 C 1.0621(7) 0.7955(4) 1.04242(19) 0.0196(9) Uani 1 1 d . . .
C2 C 1.1873(7) 0.6958(4) 1.01244(19) 0.0185(8) Uani 1 1 d . . .
C3 C 1.1042(8) 0.6369(4) 0.9583(2) 0.0210(9) Uani 1 1 d . . .
C4 C 0.8923(7) 0.6751(4) 0.93163(18) 0.0182(8) Uani 1 1 d . . .
C5 C 0.7628(7) 0.7754(4) 0.9613(2) 0.0202(9) Uani 1 1 d . . .
C6 C 0.8477(7) 0.8343(4) 1.01536(19) 0.0203(9) Uani 1 1 d . . .
F1 F 1.3960(4) 0.6537(3) 1.03662(11) 0.0255(6) Uani 1 1 d . . .
F2 F 1.2333(4) 0.5383(3) 0.93132(12) 0.0286(6) Uani 1 1 d . . .
F3 F 0.5549(4) 0.8149(3) 0.93780(12) 0.0274(6) Uani 1 1 d . . .
F4 F 0.7174(5) 0.9321(3) 1.04267(13) 0.0302(6) 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
C8A 0.024(5) 0.0340(19) 0.026(4) 0.002(2) -0.011(4) 0.002(3)
N1A 0.027(3) 0.023(3) 0.017(3) 0.001(2) -0.004(2) -0.003(2)
C7A 0.030(6) 0.022(3) 0.016(5) -0.005(3) -0.003(3) -0.005(3)
O1A 0.029(10) 0.020(3) 0.032(4) 0.005(3) -0.001(8) -0.006(5)
C9A 0.024(5) 0.0340(19) 0.026(4) 0.002(2) -0.011(4) 0.002(3)
O1B 0.029(10) 0.020(3) 0.032(4) 0.005(3) -0.001(8) -0.006(5)
C7B 0.030(6) 0.022(3) 0.016(5) -0.005(3) -0.003(3) -0.005(3)
N1B 0.027(3) 0.023(3) 0.017(3) 0.001(2) -0.004(2) -0.003(2)
C8B 0.024(5) 0.0340(19) 0.026(4) 0.002(2) -0.011(4) 0.002(3)
C9B 0.024(5) 0.0340(19) 0.026(4) 0.002(2) -0.011(4) 0.002(3)
Br1 0.0291(3) 0.0241(3) 0.0205(3) -0.00097(16) 0.00188(18) -0.00333(16)
Br2 0.0313(3) 0.0401(3) 0.0198(3) -0.00125(19) -0.00268(19) -0.00225(19)
C1 0.024(2) 0.0135(19) 0.022(2) 0.0058(15) 0.0041(17) -0.0007(15)
C2 0.013(2) 0.020(2) 0.022(2) 0.0060(16) 0.0006(16) 0.0019(15)
C3 0.022(2) 0.020(2) 0.022(2) 0.0012(17) 0.0064(17) 0.0039(16)
C4 0.020(2) 0.0196(19) 0.015(2) 0.0013(16) 0.0002(16) -0.0041(16)
C5 0.015(2) 0.021(2) 0.025(2) 0.0062(17) 0.0018(17) 0.0036(15)
C6 0.020(2) 0.0170(19) 0.025(2) 0.0041(17) 0.0081(18) 0.0022(16)
F1 0.0156(13) 0.0342(14) 0.0259(14) 0.0047(11) -0.0018(10) 0.0073(10)
F2 0.0262(14) 0.0309(14) 0.0290(15) -0.0047(12) 0.0043(11) 0.0121(11)
F3 0.0174(14) 0.0331(14) 0.0308(15) 0.0071(11) -0.0020(11) 0.0056(10)
F4 0.0263(15) 0.0276(14) 0.0381(16) -0.0031(12) 0.0095(12) 0.0102(11)

_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
C8A C7A 1.530(15) . ?
C8A H8A1 0.9700 . ?
C8A H8A2 0.9700 . ?
C8A H8A3 0.9700 . ?
N1A C7A 1.350(8) . ?
N1A C9A 1.378(10) . ?
N1A H1A 0.8700 . ?
C7A O1A 1.228(18) . ?
C9A H9A1 0.9700 . ?
C9A H9A2 0.9700 . ?
C9A H9A3 0.9700 . ?
O1B C7B 1.236(15) . ?
C7B N1B 1.351(8) . ?
C7B C8B 1.590(13) . ?
N1B C9B 1.387(9) . ?
N1B H1B 0.8700 . ?
C8B H8B1 0.9700 . ?
C8B H8B2 0.9700 . ?
C8B H8B3 0.9700 . ?
C9B H9B1 0.9700 . ?
C9B H9B2 0.9700 . ?
C9B H9B3 0.9700 . ?
Br1 C1 1.867(4) . ?
Br2 C4 1.866(4) . ?
C1 C2 1.377(6) . ?
C1 C6 1.392(6) . ?
C2 F1 1.349(5) . ?
C2 C3 1.372(6) . ?
C3 F2 1.349(5) . ?
C3 C4 1.375(6) . ?
C4 C5 1.391(6) . ?
C5 F3 1.333(5) . ?
C5 C6 1.375(6) . ?
C6 F4 1.352(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7A N1A C9A 115.0(13) . . ?
C7A N1A H1A 122.5 . . ?
C9A N1A H1A 122.5 . . ?
O1A C7A N1A 124(2) . . ?
O1A C7A C8A 117(2) . . ?
N1A C7A C8A 118.7(12) . . ?
O1B C7B N1B 123.1(13) . . ?
O1B C7B C8B 123.0(15) . . ?
N1B C7B C8B 113.7(9) . . ?
C7B N1B C9B 125.0(10) . . ?
C7B N1B H1B 117.5 . . ?
C9B N1B H1B 117.5 . . ?
C7B C8B H8B1 109.5 . . ?
C7B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
C7B C8B H8B3 109.5 . . ?
H8B1 C8B H8B3 109.5 . . ?
H8B2 C8B H8B3 109.5 . . ?
N1B C9B H9B1 109.5 . . ?
N1B C9B H9B2 109.5 . . ?
H9B1 C9B H9B2 109.5 . . ?
N1B C9B H9B3 109.5 . . ?
H9B1 C9B H9B3 109.5 . . ?
H9B2 C9B H9B3 109.5 . . ?
C2 C1 C6 117.1(4) . . ?
C2 C1 Br1 121.5(3) . . ?
C6 C1 Br1 121.5(3) . . ?
F1 C2 C3 118.8(4) . . ?
F1 C2 C1 119.7(4) . . ?
C3 C2 C1 121.5(4) . . ?
F2 C3 C2 119.0(4) . . ?
F2 C3 C4 119.6(4) . . ?
C2 C3 C4 121.4(4) . . ?
C3 C4 C5 117.9(4) . . ?
C3 C4 Br2 122.0(3) . . ?
C5 C4 Br2 120.1(3) . . ?
F3 C5 C6 119.2(4) . . ?
F3 C5 C4 120.5(4) . . ?
C6 C5 C4 120.3(4) . . ?
F4 C6 C5 118.6(4) . . ?
F4 C6 C1 119.7(4) . . ?
C5 C6 C1 121.8(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
C9A N1A C7A O1A 16(3) . . . . ?
C9A N1A C7A C8A -167(2) . . . . ?
O1B C7B N1B C9B 3(3) . . . . ?
C8B C7B N1B C9B -172.3(18) . . . . ?
C6 C1 C2 F1 -179.8(3) . . . . ?
Br1 C1 C2 F1 0.8(5) . . . . ?
C6 C1 C2 C3 -0.2(6) . . . . ?
Br1 C1 C2 C3 -179.7(3) . . . . ?
F1 C2 C3 F2 0.3(6) . . . . ?
C1 C2 C3 F2 -179.2(4) . . . . ?
F1 C2 C3 C4 179.7(4) . . . . ?
C1 C2 C3 C4 0.2(6) . . . . ?
F2 C3 C4 C5 179.1(4) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?
F2 C3 C4 Br2 -0.3(6) . . . . ?
C2 C3 C4 Br2 -179.7(3) . . . . ?
C3 C4 C5 F3 -179.1(4) . . . . ?
Br2 C4 C5 F3 0.3(5) . . . . ?
C3 C4 C5 C6 0.5(6) . . . . ?
Br2 C4 C5 C6 180.0(3) . . . . ?
F3 C5 C6 F4 -0.7(6) . . . . ?
C4 C5 C6 F4 179.6(4) . . . . ?
F3 C5 C6 C1 179.0(4) . . . . ?
C4 C5 C6 C1 -0.6(6) . . . . ?
C2 C1 C6 F4 -179.8(4) . . . . ?
Br1 C1 C6 F4 -0.3(5) . . . . ?
C2 C1 C6 C5 0.5(6) . . . . ?
Br1 C1 C6 C5 179.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.700
_refine_diff_density_min         -0.951
_refine_diff_density_rms         0.164
_database_code_depnum_ccdc_archive 'CCDC 899781'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_12DITFB-NMA
#TrackingRef 'CIFs.cif'

#===============================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
1,2-Diiodotetrafluorobenzene N-Methylacetamide
;
_chemical_name_common            ?
_chemical_melting_point          340(2)
_chemical_formula_moiety         '(C6 I2 F4), (C3 H7 N O)'

_chemical_formula_sum            'C9 H7 F4 I2 N O'
_chemical_formula_weight         474.96

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

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

_cell_length_a                   7.2201(3)
_cell_length_b                   8.6847(3)
_cell_length_c                   21.5893(8)
_cell_angle_alpha                85.660(2)
_cell_angle_beta                 81.022(2)
_cell_angle_gamma                74.403(2)
_cell_volume                     1287.11(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    401
_cell_measurement_theta_min      0.89
_cell_measurement_theta_max      28.78

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    4.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4249
_exptl_absorpt_correction_T_max  0.6390
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            49634
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         0.96
_diffrn_reflns_theta_max         25.99
_reflns_number_total             5024
_reflns_number_gt                4352
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0429P)²+1.3684P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0039(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5024
_refine_ls_number_parameters     336
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0809
_refine_ls_wR_factor_gt          0.0709
_refine_ls_goodness_of_fit_ref   1.234
_refine_ls_restrained_S_all      1.235
_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
O1A O 0.3050(9) -0.0499(8) 0.2002(5) 0.0236(16) Uani 0.870(7) 1 d PD A 1
N1A N 0.1483(6) 0.1969(5) 0.2340(2) 0.0232(12) Uani 0.870(7) 1 d PD A 1
H1A H 0.1581 0.2860 0.2484 0.028 Uiso 0.870(7) 1 calc PR A 1
C7A C 0.3105(8) 0.0775(6) 0.2210(3) 0.0227(14) Uani 0.870(7) 1 d PD A 1
C8A C 0.5014(11) 0.1087(17) 0.2332(7) 0.0305(16) Uani 0.870(7) 1 d PD A 1
H8A1 H 0.5502 0.0389 0.2682 0.046 Uiso 0.870(7) 1 calc PR A 1
H8A2 H 0.4777 0.2207 0.2438 0.046 Uiso 0.870(7) 1 calc PR A 1
H8A3 H 0.5978 0.0862 0.1955 0.046 Uiso 0.870(7) 1 calc PR A 1
C9A C -0.0352(9) 0.1848(9) 0.2252(4) 0.0305(16) Uani 0.870(7) 1 d PD A 1
H9A1 H -0.0276 0.1431 0.1837 0.046 Uiso 0.870(7) 1 calc PR A 1
H9A2 H -0.1275 0.2907 0.2283 0.046 Uiso 0.870(7) 1 calc PR A 1
H9A3 H -0.0790 0.1120 0.2576 0.046 Uiso 0.870(7) 1 calc PR A 1
O1C O 0.1459(18) 0.4693(11) 0.3019(5) 0.024(2) Uani 0.769(7) 1 d PD B 1
N1C N 0.1118(8) 0.7097(6) 0.2514(2) 0.0251(13) Uani 0.769(7) 1 d PD B 1
H1C H 0.1660 0.7884 0.2392 0.030 Uiso 0.769(7) 1 calc PR B 1
C7C C 0.2137(10) 0.5827(7) 0.2821(3) 0.0225(17) Uani 0.769(7) 1 d PD B 1
C8C C 0.4189(14) 0.5879(13) 0.2907(5) 0.0269(15) Uani 0.769(7) 1 d PD B 1
H8C1 H 0.4359 0.5659 0.3350 0.040 Uiso 0.769(7) 1 calc PR B 1
H8C2 H 0.4368 0.6942 0.2778 0.040 Uiso 0.769(7) 1 calc PR B 1
H8C3 H 0.5150 0.5071 0.2650 0.040 Uiso 0.769(7) 1 calc PR B 1
C9C C -0.0723(11) 0.7241(10) 0.2380(5) 0.0269(15) Uani 0.769(7) 1 d PD B 1
H9C1 H -0.0768 0.6247 0.2203 0.040 Uiso 0.769(7) 1 calc PR B 1
H9C2 H -0.1059 0.8131 0.2076 0.040 Uiso 0.769(7) 1 calc PR B 1
H9C3 H -0.1654 0.7447 0.2766 0.040 Uiso 0.769(7) 1 calc PR B 1
O1B O 0.257(9) -0.049(6) 0.204(4) 0.0236(16) Uani 0.130(7) 1 d PD A 2
N1B N 0.300(5) 0.177(4) 0.2353(15) 0.0232(12) Uani 0.130(7) 1 d PD A 2
H1B H 0.2564 0.2742 0.2498 0.028 Uiso 0.130(7) 1 calc PR A 2
C7B C 0.184(5) 0.088(4) 0.2193(17) 0.0227(14) Uani 0.130(7) 1 d PD A 2
C9B C 0.494(6) 0.095(12) 0.226(5) 0.0305(16) Uani 0.130(7) 1 d PD A 2
H9B1 H 0.5076 -0.0175 0.2392 0.046 Uiso 0.130(7) 1 calc PR A 2
H9B2 H 0.5668 0.1422 0.2500 0.046 Uiso 0.130(7) 1 calc PR A 2
H9B3 H 0.5443 0.1013 0.1810 0.046 Uiso 0.130(7) 1 calc PR A 2
C8B C -0.039(6) 0.145(7) 0.220(4) 0.0305(16) Uani 0.130(7) 1 d PD A 2
H8B1 H -0.0664 0.1919 0.1782 0.046 Uiso 0.130(7) 1 calc PR A 2
H8B2 H -0.0956 0.2254 0.2514 0.046 Uiso 0.130(7) 1 calc PR A 2
H8B3 H -0.0946 0.0535 0.2292 0.046 Uiso 0.130(7) 1 calc PR A 2
O1D O 0.107(7) 0.468(4) 0.293(2) 0.024(2) Uani 0.231(7) 1 d PD B 2
N1D N 0.271(2) 0.665(2) 0.2724(8) 0.0251(13) Uani 0.231(7) 1 d PD B 2
H1D H 0.2787 0.7584 0.2546 0.030 Uiso 0.231(7) 1 calc PR B 2
C7D C 0.115(3) 0.603(3) 0.2725(12) 0.0225(17) Uani 0.231(7) 1 d PD B 2
C9D C 0.415(5) 0.566(5) 0.3033(19) 0.0269(15) Uani 0.231(7) 1 d PD B 2
H9D1 H 0.3565 0.5304 0.3441 0.040 Uiso 0.231(7) 1 calc PR B 2
H9D2 H 0.5090 0.6241 0.3097 0.040 Uiso 0.231(7) 1 calc PR B 2
H9D3 H 0.4814 0.4725 0.2781 0.040 Uiso 0.231(7) 1 calc PR B 2
C8D C -0.080(4) 0.689(4) 0.2480(19) 0.0269(15) Uani 0.231(7) 1 d PD B 2
H8D1 H -0.1661 0.6176 0.2534 0.040 Uiso 0.231(7) 1 calc PR B 2
H8D2 H -0.0544 0.7192 0.2034 0.040 Uiso 0.231(7) 1 calc PR B 2
H8D3 H -0.1433 0.7859 0.2718 0.040 Uiso 0.231(7) 1 calc PR B 2
I1 I 0.20724(5) 0.24041(3) 0.401515(14) 0.02054(11) Uani 1 1 d . . .
I2 I 0.14416(5) 0.30407(4) 0.571982(16) 0.02940(12) Uani 1 1 d . . .
I3 I 0.69385(5) 0.82699(4) -0.055045(14) 0.02107(11) Uani 1 1 d . . .
I4 I 0.53938(5) 0.72944(4) 0.111741(14) 0.02083(11) Uani 1 1 d . . .
F1 F 0.2311(5) -0.0376(4) 0.63724(14) 0.0359(8) Uani 1 1 d . . .
F2 F 0.3195(5) -0.3338(4) 0.59460(15) 0.0352(8) Uani 1 1 d . . .
F3 F 0.3565(5) -0.3796(3) 0.46932(16) 0.0363(8) Uani 1 1 d . . .
F4 F 0.3093(5) -0.1288(3) 0.38804(14) 0.0327(7) Uani 1 1 d . . .
F5 F 0.6547(4) 0.3571(3) 0.12470(14) 0.0302(7) Uani 1 1 d . . .
F6 F 0.8304(4) 0.1221(3) 0.04492(16) 0.0339(8) Uani 1 1 d . . .
F7 F 0.9521(4) 0.1941(4) -0.07691(15) 0.0334(7) Uani 1 1 d . . .
F8 F 0.8922(4) 0.5000(3) -0.11848(14) 0.0306(7) Uani 1 1 d . . .
C1 C 0.2415(7) 0.0542(6) 0.4700(2) 0.0191(10) Uani 1 1 d . . .
C2 C 0.2210(7) 0.0777(6) 0.5343(2) 0.0210(11) Uani 1 1 d . . .
C3 C 0.2492(7) -0.0557(6) 0.5748(2) 0.0259(12) Uani 1 1 d . . .
C4 C 0.2943(8) -0.2082(6) 0.5543(3) 0.0262(12) Uani 1 1 d . . .
C5 C 0.3144(7) -0.2307(6) 0.4905(3) 0.0256(12) Uani 1 1 d . . .
C6 C 0.2882(7) -0.1013(6) 0.4497(2) 0.0222(11) Uani 1 1 d . . .
C7 C 0.7398(7) 0.5929(5) -0.0180(2) 0.0188(10) Uani 1 1 d . . .
C8 C 0.6791(7) 0.5576(6) 0.0453(2) 0.0185(10) Uani 1 1 d . . .
C9 C 0.7120(7) 0.3979(6) 0.0647(2) 0.0223(11) Uani 1 1 d . . .
C10 C 0.8025(7) 0.2741(6) 0.0244(3) 0.0249(12) Uani 1 1 d . . .
C11 C 0.8635(7) 0.3112(6) -0.0370(3) 0.0252(11) Uani 1 1 d . . .
C12 C 0.8316(7) 0.4703(6) -0.0580(2) 0.0209(11) 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
O1A 0.031(5) 0.0177(18) 0.023(3) -0.0018(15) 0.004(3) -0.011(2)
N1A 0.029(3) 0.019(3) 0.020(3) -0.0001(19) 0.000(2) -0.006(2)
C7A 0.036(4) 0.022(3) 0.008(3) 0.004(2) 0.002(3) -0.009(3)
C8A 0.030(2) 0.032(3) 0.029(3) -0.006(3) -0.0023(18) -0.008(2)
C9A 0.030(2) 0.032(3) 0.029(3) -0.006(3) -0.0023(18) -0.008(2)
O1C 0.041(6) 0.0177(19) 0.017(4) 0.000(2) -0.004(3) -0.014(3)
N1C 0.030(3) 0.021(3) 0.021(3) -0.002(2) 0.003(2) -0.004(2)
C7C 0.033(5) 0.017(3) 0.013(3) -0.003(2) 0.006(3) -0.005(4)
C8C 0.042(3) 0.018(4) 0.019(4) 0.005(2) 0.004(2) -0.011(2)
C9C 0.042(3) 0.018(4) 0.019(4) 0.005(2) 0.004(2) -0.011(2)
O1B 0.031(5) 0.0177(18) 0.023(3) -0.0018(15) 0.004(3) -0.011(2)
N1B 0.029(3) 0.019(3) 0.020(3) -0.0001(19) 0.000(2) -0.006(2)
C7B 0.036(4) 0.022(3) 0.008(3) 0.004(2) 0.002(3) -0.009(3)
C9B 0.030(2) 0.032(3) 0.029(3) -0.006(3) -0.0023(18) -0.008(2)
C8B 0.030(2) 0.032(3) 0.029(3) -0.006(3) -0.0023(18) -0.008(2)
O1D 0.041(6) 0.0177(19) 0.017(4) 0.000(2) -0.004(3) -0.014(3)
N1D 0.030(3) 0.021(3) 0.021(3) -0.002(2) 0.003(2) -0.004(2)
C7D 0.033(5) 0.017(3) 0.013(3) -0.003(2) 0.006(3) -0.005(4)
C9D 0.042(3) 0.018(4) 0.019(4) 0.005(2) 0.004(2) -0.011(2)
C8D 0.042(3) 0.018(4) 0.019(4) 0.005(2) 0.004(2) -0.011(2)
I1 0.02524(19) 0.01780(17) 0.01686(18) 0.00294(12) 0.00044(13) -0.00558(13)
I2 0.0365(2) 0.0276(2) 0.0217(2) -0.00747(14) 0.00079(15) -0.00532(15)
I3 0.02663(19) 0.01799(18) 0.01740(18) 0.00306(12) -0.00233(13) -0.00525(13)
I4 0.0278(2) 0.02111(18) 0.01466(18) -0.00016(12) -0.00296(13) -0.00829(14)
F1 0.044(2) 0.047(2) 0.0166(17) 0.0065(13) -0.0034(14) -0.0147(16)
F2 0.0369(19) 0.0308(17) 0.038(2) 0.0208(14) -0.0099(15) -0.0116(14)
F3 0.044(2) 0.0155(15) 0.049(2) 0.0004(13) -0.0085(16) -0.0063(14)
F4 0.050(2) 0.0212(15) 0.0260(18) -0.0042(12) -0.0065(14) -0.0057(14)
F5 0.0358(18) 0.0281(16) 0.0262(17) 0.0113(12) -0.0044(13) -0.0109(14)
F6 0.0295(17) 0.0176(15) 0.053(2) 0.0070(14) -0.0062(15) -0.0046(13)
F7 0.0301(18) 0.0247(16) 0.042(2) -0.0129(14) -0.0030(14) 0.0012(13)
F8 0.0369(18) 0.0264(16) 0.0237(17) -0.0049(12) 0.0014(13) -0.0020(13)
C1 0.016(2) 0.022(2) 0.019(3) 0.0036(19) 0.0011(19) -0.007(2)
C2 0.022(3) 0.022(3) 0.020(3) -0.0009(19) 0.001(2) -0.008(2)
C3 0.018(3) 0.036(3) 0.022(3) 0.005(2) -0.002(2) -0.005(2)
C4 0.028(3) 0.021(3) 0.030(3) 0.013(2) -0.006(2) -0.010(2)
C5 0.023(3) 0.018(3) 0.037(3) 0.003(2) -0.009(2) -0.007(2)
C6 0.024(3) 0.024(3) 0.019(3) -0.004(2) 0.000(2) -0.008(2)
C7 0.019(3) 0.016(2) 0.022(3) 0.0033(19) -0.007(2) -0.0056(19)
C8 0.015(2) 0.021(2) 0.021(3) -0.0008(19) -0.0060(19) -0.0046(19)
C9 0.022(3) 0.022(3) 0.025(3) 0.007(2) -0.008(2) -0.009(2)
C10 0.016(3) 0.014(2) 0.046(4) 0.005(2) -0.014(2) -0.004(2)
C11 0.019(3) 0.020(3) 0.036(3) -0.010(2) -0.004(2) -0.001(2)
C12 0.019(3) 0.024(3) 0.020(3) -0.001(2) -0.003(2) -0.005(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
O1A C7A 1.237(8) . ?
N1A C7A 1.347(6) . ?
N1A C9A 1.399(7) . ?
N1A H1A 0.8800 . ?
C7A C8A 1.538(10) . ?
C8A H8A1 0.9800 . ?
C8A H8A2 0.9800 . ?
C8A H8A3 0.9800 . ?
C9A H9A1 0.9800 . ?
C9A H9A2 0.9800 . ?
C9A H9A3 0.9800 . ?
O1C C7C 1.234(9) . ?
N1C C7C 1.342(7) . ?
N1C C9C 1.376(8) . ?
N1C H1C 0.8800 . ?
C7C C8C 1.535(11) . ?
C8C H8C1 0.9800 . ?
C8C H8C2 0.9800 . ?
C8C H8C3 0.9800 . ?
C9C H9C1 0.9800 . ?
C9C H9C2 0.9800 . ?
C9C H9C3 0.9800 . ?
O1B C7B 1.22(2) . ?
N1B C7B 1.377(10) . ?
N1B C9B 1.379(10) . ?
N1B H1B 0.8800 . ?
C7B C8B 1.55(2) . ?
C9B H9B1 0.9800 . ?
C9B H9B2 0.9800 . ?
C9B H9B3 0.9800 . ?
C8B H8B1 0.9800 . ?
C8B H8B2 0.9800 . ?
C8B H8B3 0.9800 . ?
O1D C7D 1.226(19) . ?
N1D C7D 1.376(10) . ?
N1D C9D 1.385(10) . ?
N1D H1D 0.8800 . ?
C7D C8D 1.564(19) . ?
C9D H9D1 0.9800 . ?
C9D H9D2 0.9800 . ?
C9D H9D3 0.9800 . ?
C8D H8D1 0.9800 . ?
C8D H8D2 0.9800 . ?
C8D H8D3 0.9800 . ?
I1 C1 2.097(5) . ?
I2 C2 2.086(5) . ?
I3 C7 2.087(4) . ?
I4 C8 2.090(5) . ?
F1 C3 1.352(6) . ?
F2 C4 1.334(6) . ?
F3 C5 1.345(6) . ?
F4 C6 1.348(6) . ?
F5 C9 1.347(6) . ?
F6 C10 1.332(6) . ?
F7 C11 1.340(6) . ?
F8 C12 1.340(6) . ?
C1 C6 1.389(7) . ?
C1 C2 1.398(7) . ?
C2 C3 1.387(7) . ?
C3 C4 1.366(8) . ?
C4 C5 1.385(8) . ?
C5 C6 1.364(7) . ?
C7 C12 1.378(7) . ?
C7 C8 1.405(7) . ?
C8 C9 1.387(7) . ?
C9 C10 1.389(7) . ?
C10 C11 1.373(8) . ?
C11 C12 1.390(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
C7A N1A C9A 122.5(5) . . ?
C7A N1A H1A 118.8 . . ?
C9A N1A H1A 118.8 . . ?
O1A C7A N1A 121.4(6) . . ?
O1A C7A C8A 122.2(6) . . ?
N1A C7A C8A 116.4(6) . . ?
C7C N1C C9C 123.9(6) . . ?
C7C N1C H1C 118.1 . . ?
C9C N1C H1C 118.1 . . ?
O1C C7C N1C 121.8(7) . . ?
O1C C7C C8C 122.5(7) . . ?
N1C C7C C8C 115.7(6) . . ?
C7B N1B C9B 112(5) . . ?
C7B N1B H1B 124.2 . . ?
C9B N1B H1B 124.2 . . ?
O1B C7B N1B 119(5) . . ?
O1B C7B C8B 115(5) . . ?
N1B C7B C8B 126(4) . . ?
N1B C9B H9B1 109.5 . . ?
N1B C9B H9B2 109.5 . . ?
H9B1 C9B H9B2 109.5 . . ?
N1B C9B H9B3 109.5 . . ?
H9B1 C9B H9B3 109.5 . . ?
H9B2 C9B H9B3 109.5 . . ?
C7B C8B H8B1 109.5 . . ?
C7B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
C7B C8B H8B3 109.5 . . ?
H8B1 C8B H8B3 109.5 . . ?
H8B2 C8B H8B3 109.5 . . ?
C7D N1D C9D 113(2) . . ?
C7D N1D H1D 123.7 . . ?
C9D N1D H1D 123.7 . . ?
O1D C7D N1D 125(3) . . ?
O1D C7D C8D 109(3) . . ?
N1D C7D C8D 126(2) . . ?
N1D C9D H9D1 109.5 . . ?
N1D C9D H9D2 109.5 . . ?
H9D1 C9D H9D2 109.5 . . ?
N1D C9D H9D3 109.5 . . ?
H9D1 C9D H9D3 109.5 . . ?
H9D2 C9D H9D3 109.5 . . ?
C7D C8D H8D1 109.5 . . ?
C7D C8D H8D2 109.5 . . ?
H8D1 C8D H8D2 109.5 . . ?
C7D C8D H8D3 109.5 . . ?
H8D1 C8D H8D3 109.5 . . ?
H8D2 C8D H8D3 109.5 . . ?
C6 C1 C2 118.5(4) . . ?
C6 C1 I1 117.6(4) . . ?
C2 C1 I1 123.9(3) . . ?
C3 C2 C1 118.4(4) . . ?
C3 C2 I2 118.7(4) . . ?
C1 C2 I2 122.9(3) . . ?
F1 C3 C4 117.4(5) . . ?
F1 C3 C2 120.0(5) . . ?
C4 C3 C2 122.6(5) . . ?
F2 C4 C3 121.0(5) . . ?
F2 C4 C5 120.2(5) . . ?
C3 C4 C5 118.8(5) . . ?
F3 C5 C6 120.5(5) . . ?
F3 C5 C4 119.8(4) . . ?
C6 C5 C4 119.7(5) . . ?
F4 C6 C5 117.7(4) . . ?
F4 C6 C1 120.2(4) . . ?
C5 C6 C1 122.1(5) . . ?
C12 C7 C8 119.8(4) . . ?
C12 C7 I3 117.9(4) . . ?
C8 C7 I3 122.3(3) . . ?
C9 C8 C7 117.8(4) . . ?
C9 C8 I4 117.8(4) . . ?
C7 C8 I4 124.4(3) . . ?
F5 C9 C8 120.3(5) . . ?
F5 C9 C10 117.1(4) . . ?
C8 C9 C10 122.6(5) . . ?
F6 C10 C11 120.6(5) . . ?
F6 C10 C9 120.6(5) . . ?
C11 C10 C9 118.7(4) . . ?
F7 C11 C10 120.0(5) . . ?
F7 C11 C12 120.0(5) . . ?
C10 C11 C12 120.0(5) . . ?
F8 C12 C7 121.2(4) . . ?
F8 C12 C11 117.7(4) . . ?
C7 C12 C11 121.1(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
C9A N1A C7A O1A 0.3(10) . . . . ?
C9A N1A C7A C8A -179.8(10) . . . . ?
C9C N1C C7C O1C -1.5(13) . . . . ?
C9C N1C C7C C8C 178.3(10) . . . . ?
C9B N1B C7B O1B 6(8) . . . . ?
C9B N1B C7B C8B -176(8) . . . . ?
C9D N1D C7D O1D -6(5) . . . . ?
C9D N1D C7D C8D 173(4) . . . . ?
C6 C1 C2 C3 0.3(7) . . . . ?
I1 C1 C2 C3 -179.4(4) . . . . ?
C6 C1 C2 I2 -178.3(4) . . . . ?
I1 C1 C2 I2 1.9(6) . . . . ?
C1 C2 C3 F1 179.8(4) . . . . ?
I2 C2 C3 F1 -1.5(6) . . . . ?
C1 C2 C3 C4 -0.6(8) . . . . ?
I2 C2 C3 C4 178.1(4) . . . . ?
F1 C3 C4 F2 -0.1(7) . . . . ?
C2 C3 C4 F2 -179.7(5) . . . . ?
F1 C3 C4 C5 -179.8(4) . . . . ?
C2 C3 C4 C5 0.6(8) . . . . ?
F2 C4 C5 F3 1.1(7) . . . . ?
C3 C4 C5 F3 -179.2(5) . . . . ?
F2 C4 C5 C6 180.0(5) . . . . ?
C3 C4 C5 C6 -0.3(8) . . . . ?
F3 C5 C6 F4 -1.1(7) . . . . ?
C4 C5 C6 F4 180.0(4) . . . . ?
F3 C5 C6 C1 179.0(4) . . . . ?
C4 C5 C6 C1 0.1(8) . . . . ?
C2 C1 C6 F4 -180.0(4) . . . . ?
I1 C1 C6 F4 -0.2(6) . . . . ?
C2 C1 C6 C5 -0.1(7) . . . . ?
I1 C1 C6 C5 179.7(4) . . . . ?
C12 C7 C8 C9 -1.1(7) . . . . ?
I3 C7 C8 C9 178.3(3) . . . . ?
C12 C7 C8 I4 179.7(4) . . . . ?
I3 C7 C8 I4 -0.9(6) . . . . ?
C7 C8 C9 F5 -179.2(4) . . . . ?
I4 C8 C9 F5 0.1(6) . . . . ?
C7 C8 C9 C10 0.4(7) . . . . ?
I4 C8 C9 C10 179.6(4) . . . . ?
F5 C9 C10 F6 -0.1(7) . . . . ?
C8 C9 C10 F6 -179.6(4) . . . . ?
F5 C9 C10 C11 -179.7(4) . . . . ?
C8 C9 C10 C11 0.7(7) . . . . ?
F6 C10 C11 F7 0.0(7) . . . . ?
C9 C10 C11 F7 179.7(4) . . . . ?
F6 C10 C11 C12 179.3(4) . . . . ?
C9 C10 C11 C12 -1.0(7) . . . . ?
C8 C7 C12 F8 -179.6(4) . . . . ?
I3 C7 C12 F8 1.0(6) . . . . ?
C8 C7 C12 C11 0.8(7) . . . . ?
I3 C7 C12 C11 -178.7(4) . . . . ?
F7 C11 C12 F8 -0.1(7) . . . . ?
C10 C11 C12 F8 -179.3(4) . . . . ?
F7 C11 C12 C7 179.6(4) . . . . ?
C10 C11 C12 C7 0.3(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.416
_refine_diff_density_min         -0.964
_refine_diff_density_rms         0.312
_database_code_depnum_ccdc_archive 'CCDC 899782'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sn062

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 1,3-Diiodotetrafluorobenzene N-Methylacetamide
;
_chemical_name_common            ?
_chemical_melting_point          348(2)
_chemical_formula_moiety         '(C6 I2 F4), (C3 H7 N O)'
_chemical_formula_sum            'C9 H7 F4 I2 N O'
_chemical_formula_weight         474.96

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14


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

_cell_length_a                   8.0655(5)
_cell_length_b                   18.2945(10)
_cell_length_c                   9.1049(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.695(3)
_cell_angle_gamma                90.00
_cell_volume                     1293.38(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    240
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      28.3

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    4.894
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.4410
_exptl_absorpt_correction_T_max  0.7578
_exptl_absorpt_process_details   SADABS

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            34556
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         28.33
_reflns_number_total             3213
_reflns_number_gt                2609
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0164P)²+0.9574P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3213
_refine_ls_number_parameters     205
_refine_ls_number_restraints     111
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0210
_refine_ls_wR_factor_ref         0.0431
_refine_ls_wR_factor_gt          0.0398
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.004
_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
O1A O 0.399(2) 0.6847(8) 0.744(2) 0.0190(14) Uani 0.50 1 d PU A 1
N1A N 0.4563(6) 0.7625(2) 0.5727(6) 0.0208(9) Uani 0.50 1 d PDU A 1
H1A H 0.4436 0.7745 0.4767 0.025 Uiso 0.50 1 calc PR A 1
C7A C 0.3756(8) 0.7053(3) 0.6109(7) 0.0194(11) Uani 0.50 1 d PDU A 1
C8A C 0.231(3) 0.6705(10) 0.465(2) 0.023(2) Uani 0.50 1 d PDU A 1
C9A C 0.564(5) 0.8034(19) 0.694(3) 0.024(4) Uani 0.50 1 d PDU A 1
O1B O 0.428(2) 0.6982(8) 0.764(2) 0.0190(14) Uani 0.50 1 d PU B 2
N1B N 0.3678(6) 0.7235(2) 0.5122(5) 0.0220(9) Uani 0.50 1 d PDU B 2
H1B H 0.3783 0.7527 0.4383 0.026 Uiso 0.50 1 calc PR B 2
C7B C 0.4488(8) 0.7341(3) 0.6546(8) 0.0209(11) Uani 0.50 1 d PDU B 2
C9B C 0.260(3) 0.6604(10) 0.486(2) 0.023(2) Uani 0.50 1 d PDU B 2
C8B C 0.587(5) 0.8016(19) 0.676(3) 0.024(4) Uani 0.50 1 d PD B 2
H9A H 0.517(5) 0.827(2) 0.749(5) 0.082(16) Uiso 1 1 d . . .
H9B H 0.683(5) 0.7851(19) 0.732(4) 0.056(11) Uiso 1 1 d . . .
H9C H 0.567(7) 0.842(3) 0.637(6) 0.103(19) Uiso 1 1 d . . .
H8A H 0.153(5) 0.6663(17) 0.516(4) 0.046(10) Uiso 1 1 d . . .
H8B H 0.298(4) 0.620(2) 0.480(4) 0.048(10) Uiso 1 1 d . . .
H8C H 0.214(4) 0.6804(18) 0.367(4) 0.051(10) Uiso 1 1 d . . .
I1 I 0.29368(2) 0.562535(8) -0.139756(18) 0.01752(5) Uani 1 1 d . . .
I2 I 0.24691(2) 0.433389(10) 0.45785(2) 0.02871(6) Uani 1 1 d . . .
F1 F 0.32962(19) 0.53981(8) 0.21235(17) 0.0237(3) Uani 1 1 d . . .
F2 F 0.0666(2) 0.31037(8) 0.21988(18) 0.0281(4) Uani 1 1 d . . .
F3 F -0.0068(2) 0.30336(8) -0.08559(19) 0.0341(4) Uani 1 1 d . . .
F4 F 0.0872(2) 0.41232(8) -0.24420(17) 0.0266(4) Uani 1 1 d . . .
C1 C 0.2138(3) 0.47850(13) -0.0195(3) 0.0165(5) Uani 1 1 d . . .
C2 C 0.2482(3) 0.48039(13) 0.1386(3) 0.0178(5) Uani 1 1 d . . .
C3 C 0.2019(3) 0.42544(13) 0.2230(3) 0.0182(5) Uani 1 1 d . . .
C4 C 0.1172(3) 0.36549(13) 0.1448(3) 0.0201(6) Uani 1 1 d . . .
C5 C 0.0782(3) 0.36152(13) -0.0115(3) 0.0205(6) Uani 1 1 d . . .
C6 C 0.1266(3) 0.41797(14) -0.0920(3) 0.0186(5) 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
O1A 0.031(5) 0.014(5) 0.013(4) -0.006(3) 0.006(3) -0.010(3)
N1A 0.031(2) 0.018(2) 0.016(2) -0.0010(19) 0.011(2) -0.0052(19)
C7A 0.025(3) 0.017(3) 0.016(3) -0.004(2) 0.006(2) 0.000(2)
C8A 0.031(6) 0.017(4) 0.017(5) 0.003(4) -0.002(3) 0.001(4)
C9A 0.021(8) 0.0310(19) 0.025(5) 0.000(3) 0.013(4) -0.004(4)
O1B 0.031(5) 0.014(5) 0.013(4) -0.006(3) 0.006(3) -0.010(3)
N1B 0.033(2) 0.020(2) 0.013(2) -0.0013(19) 0.005(2) -0.0017(19)
C7B 0.025(3) 0.014(3) 0.025(3) -0.001(2) 0.010(3) 0.005(2)
C9B 0.031(6) 0.017(4) 0.017(5) 0.003(4) -0.002(3) 0.001(4)
C8B 0.021(8) 0.0310(19) 0.025(5) 0.000(3) 0.013(4) -0.004(4)
I1 0.01726(8) 0.02180(9) 0.01505(9) 0.00376(7) 0.00701(7) 0.00230(6)
I2 0.03533(11) 0.03789(11) 0.01316(9) 0.00574(8) 0.00700(8) 0.00090(8)
F1 0.0289(8) 0.0264(8) 0.0163(8) -0.0027(6) 0.0071(7) -0.0067(6)
F2 0.0387(9) 0.0200(8) 0.0301(9) 0.0081(7) 0.0171(8) 0.0008(7)
F3 0.0502(11) 0.0235(8) 0.0316(10) -0.0082(7) 0.0164(9) -0.0111(7)
F4 0.0351(9) 0.0324(8) 0.0127(8) -0.0052(7) 0.0073(7) -0.0050(7)
C1 0.0150(12) 0.0213(12) 0.0150(13) 0.0040(10) 0.0070(11) 0.0043(10)
C2 0.0172(12) 0.0196(12) 0.0181(14) -0.0020(10) 0.0073(11) 0.0018(9)
C3 0.0166(12) 0.0252(13) 0.0136(13) 0.0027(10) 0.0053(11) 0.0071(10)
C4 0.0223(13) 0.0184(12) 0.0234(14) 0.0056(11) 0.0127(12) 0.0045(10)
C5 0.0244(14) 0.0164(12) 0.0233(15) -0.0047(11) 0.0109(12) -0.0001(10)
C6 0.0209(13) 0.0249(13) 0.0118(12) 0.0010(10) 0.0073(11) 0.0054(10)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C7A 1.23(2) . ?
N1A C7A 1.327(7) . ?
N1A C9A 1.423(18) . ?
N1A H1A 0.8800 . ?
C7A C8A 1.641(5) . ?
C8A H8A 0.88(5) . ?
C8A H8B 1.06(4) . ?
C8A H8C 0.88(4) . ?
C9A H9A 0.82(6) . ?
C9A H9B 0.99(6) . ?
C9A H9C 0.88(6) . ?
O1B C7B 1.24(2) . ?
N1B C7B 1.299(8) . ?
N1B C9B 1.424(18) . ?
N1B H1B 0.8800 . ?
C7B C8B 1.640(5) . ?
C9B H8A 0.98(5) . ?
C9B H8B 0.81(4) . ?
C9B H8C 1.11(4) . ?
C8B H9A 1.08(6) . ?
C8B H9B 0.86(6) . ?
C8B H9C 0.82(7) . ?
I1 C1 2.087(2) . ?
I2 C3 2.075(3) . ?
F1 C2 1.351(3) . ?
F2 C4 1.342(3) . ?
F3 C5 1.344(3) . ?
F4 C6 1.340(3) . ?
C1 C6 1.380(3) . ?
C1 C2 1.391(3) . ?
C2 C3 1.377(4) . ?
C3 C4 1.383(4) . ?
C4 C5 1.373(4) . ?
C5 C6 1.382(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7A N1A C9A 116.7(12) . . ?
C7A N1A H1A 121.6 . . ?
C9A N1A H1A 121.6 . . ?
O1A C7A N1A 122.8(7) . . ?
O1A C7A C8A 124.4(12) . . ?
N1A C7A C8A 112.6(10) . . ?
C7A C8A H8A 93(3) . . ?
C7A C8A H8B 91(2) . . ?
H8A C8A H8B 105(4) . . ?
C7A C8A H8C 128(3) . . ?
H8A C8A H8C 128(4) . . ?
H8B C8A H8C 104(4) . . ?
N1A C9A H9A 117(4) . . ?
N1A C9A H9B 115(4) . . ?
H9A C9A H9B 122(4) . . ?
N1A C9A H9C 94(4) . . ?
H9A C9A H9C 92(6) . . ?
H9B C9A H9C 107(5) . . ?
C7B N1B C9B 113.8(10) . . ?
C7B N1B H1B 123.1 . . ?
C9B N1B H1B 123.1 . . ?
O1B C7B N1B 125.6(8) . . ?
O1B C7B C8B 122.4(13) . . ?
N1B C7B C8B 112.0(12) . . ?
N1B C9B H8A 114(3) . . ?
N1B C9B H8B 122(3) . . ?
H8A C9B H8B 120(4) . . ?
N1B C9B H8C 85(2) . . ?
H8A C9B H8C 98(3) . . ?
H8B C9B H8C 105(4) . . ?
C7B C8B H9A 87(3) . . ?
C7B C8B H9B 106(4) . . ?
H9A C8B H9B 109(4) . . ?
C7B C8B H9C 126(5) . . ?
H9A C8B H9C 79(5) . . ?
H9B C8B H9C 128(4) . . ?
C6 C1 C2 116.6(2) . . ?
C6 C1 I1 122.01(19) . . ?
C2 C1 I1 121.41(18) . . ?
F1 C2 C3 118.6(2) . . ?
F1 C2 C1 117.9(2) . . ?
C3 C2 C1 123.5(2) . . ?
C2 C3 C4 117.5(2) . . ?
C2 C3 I2 121.71(19) . . ?
C4 C3 I2 120.70(19) . . ?
F2 C4 C5 118.2(2) . . ?
F2 C4 C3 120.6(2) . . ?
C5 C4 C3 121.2(2) . . ?
F3 C5 C4 120.3(2) . . ?
F3 C5 C6 120.3(2) . . ?
C4 C5 C6 119.4(2) . . ?
F4 C6 C1 120.2(2) . . ?
F4 C6 C5 118.0(2) . . ?
C1 C6 C5 121.8(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A N1A C7A O1A -5(3) . . . . ?
C9A N1A C7A C8A 171(2) . . . . ?
C9B N1B C7B O1B -6.0(18) . . . . ?
C9B N1B C7B C8B 173(2) . . . . ?
C6 C1 C2 F1 -178.4(2) . . . . ?
I1 C1 C2 F1 2.4(3) . . . . ?
C6 C1 C2 C3 0.8(4) . . . . ?
I1 C1 C2 C3 -178.34(18) . . . . ?
F1 C2 C3 C4 179.4(2) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
F1 C2 C3 I2 2.0(3) . . . . ?
C1 C2 C3 I2 -177.22(19) . . . . ?
C2 C3 C4 F2 -179.2(2) . . . . ?
I2 C3 C4 F2 -1.8(3) . . . . ?
C2 C3 C4 C5 -1.1(4) . . . . ?
I2 C3 C4 C5 176.33(19) . . . . ?
F2 C4 C5 F3 -0.7(4) . . . . ?
C3 C4 C5 F3 -178.8(2) . . . . ?
F2 C4 C5 C6 179.1(2) . . . . ?
C3 C4 C5 C6 1.0(4) . . . . ?
C2 C1 C6 F4 179.4(2) . . . . ?
I1 C1 C6 F4 -1.4(3) . . . . ?
C2 C1 C6 C5 -1.0(4) . . . . ?
I1 C1 C6 C5 178.17(19) . . . . ?
F3 C5 C6 F4 -0.5(4) . . . . ?
C4 C5 C6 F4 179.8(2) . . . . ?
F3 C5 C6 C1 179.9(2) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.766
_refine_diff_density_min         -0.793
_refine_diff_density_rms         0.107
_database_code_depnum_ccdc_archive 'CCDC 899783'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_sn061

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 1,4-Diiodotetrafluorobenzene N-Methylacetamide
;
_chemical_name_common            ?
_chemical_melting_point          311(2)
_chemical_formula_moiety         '(C6 F4 I2 ),(C3 H7 N O)'
_chemical_formula_sum            'C9 H7 F4 I2 N O'
_chemical_formula_weight         474.96

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   21.263(9)
_cell_length_b                   4.7949(19)
_cell_length_c                   12.348(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.64(2)
_cell_angle_gamma                90
_cell_volume                     1258.4(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    340
_cell_measurement_theta_min      0.98
_cell_measurement_theta_max      27.89

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.507
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    5.031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4181
_exptl_absorpt_correction_T_max  0.4646
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_number            7836
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.916
_diffrn_reflns_theta_max         25.983
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             1215
_reflns_number_gt                1068
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+9.5859P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1215
_refine_ls_number_parameters     103
_refine_ls_number_restraints     33
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0188
_refine_ls_wR_factor_ref         0.0543
_refine_ls_wR_factor_gt          0.0413
_refine_ls_goodness_of_fit_ref   1.249
_refine_ls_restrained_S_all      1.238
_refine_ls_shift/su_max          0.138
_refine_ls_shift/su_mean         0.018

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.11783(2) 0.02812(6) 0.63172(2) 0.02067(11) Uani 1 1 d . . . . .
F1 F 0.22341(12) 0.4710(5) 0.6943(2) 0.0231(6) Uani 1 1 d . . . . .
F2 F 0.17693(12) -0.1495(5) 0.4086(2) 0.0257(6) Uani 1 1 d . . . . .
C1 C 0.19715(19) 0.1575(9) 0.5536(4) 0.0178(9) Uani 1 1 d . . . . .
C2 C 0.2358(2) 0.3591(9) 0.5989(4) 0.0176(9) Uani 1 1 d . . . . .
C3 C 0.2125(2) 0.0498(9) 0.4549(4) 0.0180(9) Uani 1 1 d . . . . .
O1 O 0.0052(13) 0.8993(10) 0.7656(16) 0.015(3) Uani 0.5 1 d D U P A -2
N1 N -0.0176(3) 0.4738(16) 0.7047(6) 0.0211(16) Uani 0.5 1 d D U P A -2
H1 H -0.0128 0.2929 0.7137 0.025 Uiso 0.5 1 calc R U P A -2
C4 C 0.0103(5) 0.6453(15) 0.7731(7) 0.018(2) Uani 0.5 1 d D U P A -2
C5 C 0.0523(12) 0.516(3) 0.8614(16) 0.025(4) Uani 0.5 1 d D U P A -2
H5A H 0.0964 0.5610 0.8479 0.038 Uiso 0.5 1 calc R U P A -2
H5B H 0.0468 0.3130 0.8611 0.038 Uiso 0.5 1 calc R U P A -2
H5C H 0.0409 0.5906 0.9320 0.038 Uiso 0.5 1 calc R U P A -2
C6 C -0.0559(12) 0.575(3) 0.6154(15) 0.030(4) Uani 0.5 1 d D U P A -2
H6A H -0.0949 0.6535 0.6426 0.045 Uiso 0.5 1 calc R U P A -2
H6B H -0.0659 0.4202 0.5658 0.045 Uiso 0.5 1 calc R U P A -2
H6C H -0.0329 0.7192 0.5767 0.045 Uiso 0.5 1 calc R U P A -2

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
I1 0.01658(15) 0.02288(17) 0.02285(18) 0.00351(13) 0.00558(11) -0.00072(12)
F1 0.0247(13) 0.0257(14) 0.0191(14) -0.0060(11) 0.0065(11) 0.0007(11)
F2 0.0247(14) 0.0262(14) 0.0263(16) -0.0056(12) 0.0003(12) -0.0090(11)
C1 0.014(2) 0.018(2) 0.021(2) 0.0043(18) 0.0032(18) 0.0025(17)
C2 0.019(2) 0.018(2) 0.016(2) -0.0011(18) 0.0026(18) 0.0055(17)
C3 0.017(2) 0.017(2) 0.020(2) 0.0016(18) -0.0026(17) -0.0017(17)
O1 0.021(8) 0.008(2) 0.017(10) 0.002(3) 0.001(6) 0.001(3)
N1 0.017(3) 0.015(4) 0.031(4) -0.001(3) 0.004(3) -0.002(3)
C4 0.016(5) 0.016(4) 0.024(6) 0.004(3) 0.009(4) 0.003(3)
C5 0.036(8) 0.017(7) 0.023(8) -0.003(6) -0.002(6) 0.010(6)
C6 0.035(7) 0.024(8) 0.032(10) -0.003(7) 0.005(7) 0.002(7)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.063(4) . ?
F1 C2 1.327(5) . ?
F2 C3 1.337(5) . ?
C1 C3 1.371(7) . ?
C1 C2 1.378(6) . ?
C2 C3 1.371(6) 7_556 ?
C3 C2 1.371(6) 7_556 ?
O1 C4 1.226(7) . ?
N1 C4 1.308(7) . ?
N1 C6 1.436(9) . ?
N1 H1 0.8800 . ?
C4 C5 1.522(8) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C1 C2 118.1(4) . . ?
C3 C1 I1 121.4(3) . . ?
C2 C1 I1 120.5(3) . . ?
F1 C2 C3 118.9(4) . 7_556 ?
F1 C2 C1 120.8(4) . . ?
C3 C2 C1 120.2(4) 7_556 . ?
F2 C3 C1 120.2(4) . . ?
F2 C3 C2 118.1(4) . 7_556 ?
C1 C3 C2 121.6(4) . 7_556 ?
C4 N1 C6 121.3(8) . . ?
C4 N1 H1 119.3 . . ?
C6 N1 H1 119.3 . . ?
O1 C4 N1 122.6(8) . . ?
O1 C4 C5 120.5(9) . . ?
N1 C4 C5 116.9(8) . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.6 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 H6A 109.6 . . ?
N1 C6 H6B 109.4 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.4 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C1 C2 F1 180.0(4) . . . . ?
I1 C1 C2 F1 1.0(6) . . . . ?
C3 C1 C2 C3 0.9(7) . . . 7_556 ?
I1 C1 C2 C3 -178.1(3) . . . 7_556 ?
C2 C1 C3 F2 178.9(4) . . . . ?
I1 C1 C3 F2 -2.1(6) . . . . ?
C2 C1 C3 C2 -0.9(7) . . . 7_556 ?
I1 C1 C3 C2 178.1(3) . . . 7_556 ?
C6 N1 C4 O1 0(3) . . . . ?
C6 N1 C4 C5 -177(3) . . . . ?

_refine_diff_density_max         0.868
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.156

_shelxl_version_number           2013-3

_shelx_res_file                  
;
TITL SN061_0m in C2/c
CELL 0.71073  21.2631   4.7949  12.3476  90.000  91.639  90.000
ZERR    4.00   0.0087   0.0019   0.0057   0.000   0.024   0.000
LATT 7
SYMM -X, Y, 0.5-Z
SFAC C  H  N  O  F  I
UNIT 36  28  4  4  16  8
LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
L.S. 5
ACTA
BOND $H
HTAB
omit -3 52
CONF
SIZE 0.21 0.19 0.18
FMAP 2
PLAN 20
TEMP -173
WGHT    0.000000    9.585900
FVAR       0.07223  -0.72258
I1    6    0.117830    0.028122    0.631724    11.00000    0.01658    0.02288 =
         0.02285    0.00351    0.00558   -0.00072
F1    5    0.223407    0.471013    0.694272    11.00000    0.02472    0.02573 =
         0.01907   -0.00595    0.00647    0.00074
F2    5    0.176931   -0.149517    0.408578    11.00000    0.02467    0.02620 =
         0.02630   -0.00558    0.00030   -0.00905
C1    1    0.197154    0.157470    0.553566    11.00000    0.01414    0.01841 =
         0.02105    0.00425    0.00320    0.00254
C2    1    0.235848    0.359112    0.598931    11.00000    0.01900    0.01808 =
         0.01585   -0.00107    0.00265    0.00548
C3    1    0.212484    0.049809    0.454864    11.00000    0.01722    0.01658 =
         0.01997    0.00155   -0.00258   -0.00170
mole 2
dfix 1.32 0.01 N1  C4
dfix 1.44 0.01 N1  C6
dfix 1.54 0.01 C4  C5
dfix 1.22 0.01 O1  C4
dfix 2.39 0.02 O1  C5
dfix 2.41 0.02 N1  C5
dfix 2.41 0.02 C4  C6
dfix 3.77 0.02 C5  C6
dfix 2.76 0.02 O1  C6
SIMU 0.01 O1  > C6
PART -2
O1    4    0.005206    0.899320    0.765608    10.50000    0.02073    0.00818 =
         0.01652    0.00184    0.00074    0.00095
N1    3   -0.017609    0.473761    0.704728    10.50000    0.01731    0.01542 =
         0.03072   -0.00100    0.00425   -0.00165
AFIX  43
H1    2   -0.012816    0.292858    0.713692    10.50000   -1.20000
AFIX   0
C4    1    0.010269    0.645263    0.773073    10.50000    0.01620    0.01559 =
         0.02400    0.00388    0.00856    0.00278
C5    1    0.052308    0.515945    0.861396    10.50000    0.03646    0.01652 =
         0.02280   -0.00307   -0.00174    0.00951
AFIX 137
H5A   2    0.096359    0.560963    0.847941    10.50000   -1.50000
H5B   2    0.046767    0.313043    0.861064    10.50000   -1.50000
H5C   2    0.040864    0.590574    0.932045    10.50000   -1.50000
AFIX   0
C6    1   -0.055880    0.574691    0.615356    10.50000    0.03488    0.02436 =
         0.03168   -0.00266    0.00538    0.00238
AFIX 137
H6A   2   -0.094914    0.653482    0.642561    10.50000   -1.50000
H6B   2   -0.065935    0.420234    0.565849    10.50000   -1.50000
H6C   2   -0.032903    0.719223    0.576676    10.50000   -1.50000
AFIX   0
HKLF   4

REM  SN061_0m in C2/c
REM R1 =  0.0188 for    1068 Fo > 4sig(Fo)  and  0.0255 for all    1215 data
REM    103 parameters refined using     33 restraints

END

WGHT      0.0000     10.1478

REM No hydrogen bonds found for HTAB generation

REM Highest difference peak  0.868,  deepest hole -0.644,  1-sigma level  0.156
Q1    1   0.0901  0.0254  0.5787  11.00000  0.05    0.87
Q2    1   0.1111  0.1364  0.6770  11.00000  0.05    0.65
Q3    1   0.1455  0.4493  0.6035  11.00000  0.05    0.51
Q4    1   0.1508  0.0147  0.7024  11.00000  0.05    0.50
Q5    1   0.0000  0.2814  0.7500  10.50000  0.05    0.48
Q6    1   0.0729 -0.2135  0.5940  11.00000  0.05    0.47
Q7    1   0.1462  0.2940  0.6725  11.00000  0.05    0.47
Q8    1   0.1191 -0.1202  0.6407  11.00000  0.05    0.47
Q9    1   0.0350  0.9917  0.7211  11.00000  0.05    0.47
Q10   1   0.0321  0.9644  0.8227  11.00000  0.05    0.46
Q11   1  -0.0700  0.2651  0.8015  11.00000  0.05    0.45
Q12   1  -0.0529  0.7648  0.5260  11.00000  0.05    0.44
Q13   1   0.0048  0.3748  0.8603  11.00000  0.05    0.43
Q14   1   0.0374  0.5772  0.8429  11.00000  0.05    0.42
Q15   1   0.0227  0.5678  0.6155  11.00000  0.05    0.42
Q16   1  -0.0394  0.1057  0.7781  11.00000  0.05    0.42
Q17   1  -0.0938  0.3869  0.4394  11.00000  0.05    0.42
Q18   1   0.1298 -0.1312  0.5599  11.00000  0.05    0.41
Q19   1   0.0000  0.8514  0.7500  10.50000  0.05    0.41
Q20   1  -0.1035  0.8918  0.5479  11.00000  0.05    0.40
;
_shelx_res_checksum              72491
_database_code_depnum_ccdc_archive 'CCDC 899784'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_NMA
#TrackingRef 'CIFs.cif'

#==============================================================================

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
N-methylacetamide
;
_chemical_name_common            ?
_chemical_melting_point          292(2)
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3 H7 N O'
_chemical_formula_weight         73.10

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_symmetry_Int_Tables_number      62


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

_cell_length_a                   9.6481(12)
_cell_length_b                   6.3391(8)
_cell_length_c                   7.1825(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     439.28(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    450
_cell_measurement_theta_min      0.98
_cell_measurement_theta_max      27.0

_exptl_crystal_description       capillary
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.105
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             160
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9836
_exptl_absorpt_correction_T_max  0.9836
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8597
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.54
_diffrn_reflns_theta_max         25.98
_reflns_number_total             471
_reflns_number_gt                412
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0660P)²+0.3456P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         471
_refine_ls_number_parameters     33
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1344
_refine_ls_wR_factor_gt          0.1305
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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
O1 O 0.78695(16) 0.7500 0.2083(2) 0.0276(5) Uani 1 2 d S . .
N1 N 0.5595(2) 0.7500 0.1439(3) 0.0259(6) Uani 1 2 d S . .
H1 H 0.4739 0.7500 0.1866 0.031 Uiso 1 2 calc SR . .
C3 C 0.5834(3) 0.7500 -0.0551(3) 0.0267(6) Uani 1 2 d S . .
H3A H 0.6493 0.8619 -0.0868 0.040 Uiso 0.50 1 calc PR . .
H3B H 0.4956 0.7749 -0.1202 0.040 Uiso 0.50 1 calc PR . .
H3C H 0.6214 0.6132 -0.0929 0.040 Uiso 0.50 1 calc PR . .
C1 C 0.6268(3) 0.7500 0.4679(3) 0.0271(6) Uani 1 2 d S . .
H1A H 0.6780 0.8623 0.5316 0.041 Uiso 0.50 1 calc PR . .
H1B H 0.6511 0.6134 0.5228 0.041 Uiso 0.50 1 calc PR . .
H1C H 0.5270 0.7744 0.4818 0.041 Uiso 0.50 1 calc PR . .
C2 C 0.6643(2) 0.7500 0.2625(4) 0.0246(6) Uani 1 2 d S . .

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
O1 0.0120(9) 0.0389(10) 0.0321(10) 0.000 -0.0002(6) 0.000
N1 0.0180(10) 0.0315(12) 0.0283(12) 0.000 0.0006(8) 0.000
C3 0.0271(13) 0.0290(13) 0.0241(13) 0.000 0.0002(9) 0.000
C1 0.0259(13) 0.0291(13) 0.0263(14) 0.000 -0.0017(9) 0.000
C2 0.0228(13) 0.0174(11) 0.0337(14) 0.000 -0.0009(10) 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
O1 C2 1.246(3) . ?
N1 C2 1.323(3) . ?
N1 C3 1.448(3) . ?
N1 H1 0.8800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C1 C2 1.519(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C3 120.9(2) . . ?
C2 N1 H1 119.5 . . ?
C3 N1 H1 119.5 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 N1 121.7(2) . . ?
O1 C2 C1 122.0(2) . . ?
N1 C2 C1 116.3(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C2 O1 0.000(1) . . . . ?
C3 N1 C2 C1 180.0 . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.98
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.760
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.050



# start Validation Reply Form

_vrf_PLAT431_12DBrTFB-NMA        
;
PROBLEM: Short Inter HL..A Contact Br1 .. O1A . 2.80 Ang.
RESPONSE: short intermolecular Halogen...Oxygen interactions
are the clue of this paper.
;
_vrf_PLAT431_13DBrTFB-NMA        
;
PROBLEM: Short Inter HL..A Contact Br1 .. O1A . 2.71 Ang.
RESPONSE: short intermolecular Halogen...Oxygen interactions
are the clue of this paper.
;

_vrf_PLAT431_14DBrTFB-NMA        
;
PROBLEM: Short Inter HL..A Contact Br1 .. O1B . 2.86 Ang.
RESPONSE: short intermolecular Halogen...Oxygen interactions
are the clue of this paper.
;
_vrf_PLAT431_12DITFB-NMA         
;
PROBLEM: Short Inter HL..A Contact I4 .. O1A . 2.83 Ang.
RESPONSE: short intermolecular Halogen...Oxygen interactions
are the clue of this paper.
;
_vrf_PLAT431_13DITFB-NMA         
;
PROBLEM: Short Inter HL..A Contact I1 .. O1A . 2.82 Ang.
RESPONSE: short intermolecular Halogen...Oxygen interactions
are the clue of this paper.
;
_vrf_PLAT431_14DITFB-NMA         
;
PROBLEM: Short Inter HL..A Contact I1 .. O1A . 3.00 Ang.
RESPONSE: short intermolecular Halogen...Oxygen interactions
are the clue of this paper.
;


# end Validation Reply Form


#=========END


_database_code_depnum_ccdc_archive 'CCDC 899785'
