# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global

_journal_coden_Cambridge         1350

loop_
_publ_author_name
'Kumar Biradha'

_publ_contact_author_name        'Kumar Biradha'
_publ_contact_author_email       KBIRADHA@CHEM.IITKGP.ERNET.IN

_publ_section_title              
;
Halo---Halo interactions in assembling??-sheets into
two-dimensional layers in the Bis-(4-halo-phenylamido)alkanes and their
inter-halogen co-crystals
;

# Attachment 'kb.cif'

data_2I
_database_code_depnum_ccdc_archive 'CCDC 696960'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 I2 N2 O2'
_chemical_formula_weight         520.09

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'
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_H-M   P2(1)/c

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

_cell_length_a                   17.693(7)
_cell_length_b                   4.8374(19)
_cell_length_c                   9.883(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.391(10)
_cell_angle_gamma                90.00
_cell_volume                     834.5(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1819
_cell_measurement_theta_min      1.17
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    2.070
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             492
_exptl_absorpt_coefficient_mu    3.776
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.642
_exptl_absorpt_correction_T_max  0.739
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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 APEX 2 Bruker'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10095
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.17
_diffrn_reflns_theta_max         27.00
_reflns_number_total             1819
_reflns_number_gt                1628
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1000P)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     SHELXL
_refine_ls_extinction_coef       0.020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1819
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.1038
_refine_ls_wR_factor_gt          0.0979
_refine_ls_goodness_of_fit_ref   0.882
_refine_ls_restrained_S_all      0.882
_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
I1 I 0.425091(11) 0.68385(5) 0.14462(2) 0.05924(19) Uani 1 1 d . . .
N11 N 0.13471(15) 0.3520(4) -0.2792(2) 0.0404(5) Uani 1 1 d . . .
H11 H 0.1271 0.1787 -0.2955 0.048 Uiso 1 1 calc R . .
C11 C 0.19897(14) 0.4242(5) -0.1810(2) 0.0338(5) Uani 1 1 d . . .
C12 C 0.26736(19) 0.2857(6) -0.1813(3) 0.0464(7) Uani 1 1 d . . .
H12 H 0.2702 0.1459 -0.2449 0.056 Uiso 1 1 calc R . .
C13 C 0.33203(18) 0.3548(6) -0.0869(3) 0.0486(7) Uani 1 1 d . . .
H13 H 0.3779 0.2606 -0.0865 0.058 Uiso 1 1 calc R . .
C14 C 0.32711(14) 0.5651(5) 0.0060(2) 0.0378(5) Uani 1 1 d . . .
C15 C 0.25942(18) 0.7000(6) 0.0091(3) 0.0459(7) Uani 1 1 d . . .
H15 H 0.2568 0.8384 0.0735 0.055 Uiso 1 1 calc R . .
C16 C 0.19472(16) 0.6303(6) -0.0840(3) 0.0426(6) Uani 1 1 d . . .
H16 H 0.1486 0.7210 -0.0816 0.051 Uiso 1 1 calc R . .
O21 O 0.08644(14) 0.7791(4) -0.3282(2) 0.0496(5) Uani 1 1 d . . .
C21 C 0.08441(14) 0.5287(5) -0.3495(2) 0.0336(5) Uani 1 1 d . . .
C22 C 0.02558(16) 0.3988(5) -0.4597(3) 0.0447(6) Uani 1 1 d . . .
H22A H 0.0521 0.2942 -0.5214 0.054 Uiso 1 1 calc . . .
H22B H -0.0053 0.2700 -0.4168 0.054 Uiso 1 1 calc . . .

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 0.0393(2) 0.0700(3) 0.0597(2) -0.00576(8) -0.01783(13) -0.00585(7)
N11 0.0445(13) 0.0248(8) 0.0452(11) -0.0058(8) -0.0123(10) -0.0030(8)
C11 0.0351(12) 0.0293(10) 0.0332(10) 0.0032(9) -0.0055(9) -0.0033(9)
C12 0.0468(17) 0.0411(14) 0.0451(15) -0.0125(11) -0.0113(13) 0.0086(11)
C13 0.0353(14) 0.0545(15) 0.0506(15) -0.0050(12) -0.0087(12) 0.0091(11)
C14 0.0318(11) 0.0417(12) 0.0356(10) 0.0034(9) -0.0073(9) -0.0065(9)
C15 0.0408(16) 0.0548(17) 0.0388(13) -0.0149(10) -0.0039(12) 0.0016(11)
C16 0.0316(13) 0.0504(13) 0.0434(13) -0.0112(11) -0.0013(10) 0.0048(11)
O21 0.0582(14) 0.0244(8) 0.0560(12) -0.0014(8) -0.0214(10) -0.0030(8)
C21 0.0345(12) 0.0285(10) 0.0342(10) 0.0010(9) -0.0055(9) -0.0061(9)
C22 0.0457(15) 0.0289(11) 0.0513(14) -0.0019(11) -0.0166(12) -0.0058(11)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C14 2.106(2) . ?
N11 C21 1.343(3) . ?
N11 C11 1.413(3) . ?
C11 C12 1.384(4) . ?
C11 C16 1.394(4) . ?
C12 C13 1.394(4) . ?
C13 C14 1.383(4) . ?
C14 C15 1.369(4) . ?
C15 C16 1.388(4) . ?
O21 C21 1.229(3) . ?
C21 C22 1.515(3) . ?
C22 C22 1.476(5) 3_564 ?

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
C21 N11 C11 126.08(19) . . ?
C12 C11 C16 119.6(2) . . ?
C12 C11 N11 119.0(2) . . ?
C16 C11 N11 121.5(2) . . ?
C11 C12 C13 120.3(2) . . ?
C14 C13 C12 119.2(3) . . ?
C15 C14 C13 121.0(2) . . ?
C15 C14 I1 119.06(19) . . ?
C13 C14 I1 119.9(2) . . ?
C14 C15 C16 120.0(2) . . ?
C15 C16 C11 119.9(2) . . ?
O21 C21 N11 122.7(2) . . ?
O21 C21 C22 122.0(2) . . ?
N11 C21 C22 115.3(2) . . ?
C22 C22 C21 113.7(3) 3_564 . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.748
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.138

data_3I
_database_code_depnum_ccdc_archive 'CCDC 696961'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 I2 N2 O2'
_chemical_formula_weight         548.14

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'
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_H-M   P2(1)/c

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

_cell_length_a                   18.979(7)
_cell_length_b                   4.8064(18)
_cell_length_c                   10.089(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.319(10)
_cell_angle_gamma                90.00
_cell_volume                     918.7(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1993
_cell_measurement_theta_min      1.07
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.981
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             524
_exptl_absorpt_coefficient_mu    3.436
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.668
_exptl_absorpt_correction_T_max  0.762
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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 APEX 2 BRUKER'
_diffrn_measurement_method       Hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11406
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.07
_diffrn_reflns_theta_max         27.00
_reflns_number_total             1993
_reflns_number_gt                1845
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0555P)²+0.3876P] 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       0.0262(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1993
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0983
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   1.237
_refine_ls_restrained_S_all      1.237
_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
I1 I 0.431647(12) 0.68602(6) 0.15791(2) 0.05854(17) Uani 1 1 d . . .
C11 C 0.22845(15) 0.4141(6) -0.1270(3) 0.0349(6) Uani 1 1 d . . .
C12 C 0.22237(16) 0.6154(7) -0.0318(3) 0.0431(7) Uani 1 1 d . . .
H12 H 0.1791 0.7014 -0.0222 0.052 Uiso 1 1 calc R . .
C13 C 0.2801(2) 0.6912(7) 0.0499(3) 0.0467(8) Uani 1 1 d . . .
H13 H 0.2758 0.8295 0.1133 0.056 Uiso 1 1 calc R . .
C14 C 0.34417(15) 0.5617(6) 0.0373(3) 0.0383(6) Uani 1 1 d . . .
C15 C 0.35041(19) 0.3541(7) -0.0549(4) 0.0485(7) Uani 1 1 d . . .
H15 H 0.3933 0.2628 -0.0615 0.058 Uiso 1 1 calc R . .
C16 C 0.2924(2) 0.2806(7) -0.1385(4) 0.0469(8) Uani 1 1 d . . .
H16 H 0.2967 0.1420 -0.2018 0.056 Uiso 1 1 calc R . .
N21 N 0.17083(16) 0.3344(5) -0.2132(3) 0.0418(6) Uani 1 1 d . . .
H21 H 0.1643 0.1593 -0.2263 0.050 Uiso 1 1 calc R . .
O21 O 0.12618(15) 0.7612(5) -0.2583(3) 0.0517(6) Uani 1 1 d . . .
C21 C 0.12529(15) 0.5105(6) -0.2767(3) 0.0355(6) Uani 1 1 d . . .
C22 C 0.0736(2) 0.3746(7) -0.3753(4) 0.0509(8) Uani 1 1 d . . .
H22A H 0.0999 0.2694 -0.4380 0.061 Uiso 1 1 calc . . .
H22B H 0.0452 0.2436 -0.3283 0.061 Uiso 1 1 calc . . .
C23 C 0.02535(17) 0.5703(6) -0.4510(3) 0.0446(7) Uani 1 1 d . . .
H23A H 0.0535 0.7018 -0.4982 0.053 Uiso 1 1 calc . . .
H23B H -0.0013 0.6749 -0.3887 0.053 Uiso 1 1 calc . . .

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 0.0397(2) 0.0726(3) 0.0604(2) -0.00420(10) -0.02151(13) -0.00721(9)
C11 0.0346(14) 0.0328(12) 0.0359(13) 0.0019(10) -0.0105(11) -0.0015(11)
C12 0.0316(15) 0.0526(16) 0.0441(15) -0.0106(13) -0.0072(12) 0.0043(13)
C13 0.0425(19) 0.0562(19) 0.0400(16) -0.0134(13) -0.0100(14) 0.0020(13)
C14 0.0340(14) 0.0473(15) 0.0321(12) 0.0028(11) -0.0102(10) -0.0055(12)
C15 0.0330(16) 0.0579(18) 0.0533(18) -0.0056(15) -0.0091(14) 0.0090(13)
C16 0.0446(19) 0.0472(16) 0.0467(17) -0.0127(13) -0.0150(14) 0.0090(13)
N21 0.0451(16) 0.0295(11) 0.0485(14) -0.0044(9) -0.0175(12) -0.0018(9)
O21 0.0601(16) 0.0303(9) 0.0608(15) -0.0009(10) -0.0299(13) -0.0024(10)
C21 0.0372(14) 0.0315(12) 0.0363(13) 0.0002(10) -0.0095(11) -0.0036(10)
C22 0.058(2) 0.0338(13) 0.0568(18) -0.0022(13) -0.0295(16) -0.0035(14)
C23 0.0427(17) 0.0394(14) 0.0491(16) -0.0010(13) -0.0194(13) -0.0047(12)

_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 C14 2.088(3) . ?
C11 C12 1.373(4) . ?
C11 C16 1.384(4) . ?
C11 N21 1.411(4) . ?
C12 C13 1.382(5) . ?
C13 C14 1.378(5) . ?
C14 C15 1.374(5) . ?
C15 C16 1.393(5) . ?
N21 C21 1.345(4) . ?
O21 C21 1.219(4) . ?
C21 C22 1.505(4) . ?
C22 C23 1.492(5) . ?
C23 C23 1.500(6) 3_564 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C11 C16 119.7(3) . . ?
C12 C11 N21 122.0(3) . . ?
C16 C11 N21 118.4(3) . . ?
C11 C12 C13 120.4(3) . . ?
C14 C13 C12 120.0(3) . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 I1 120.4(2) . . ?
C13 C14 I1 119.5(2) . . ?
C14 C15 C16 119.8(3) . . ?
C11 C16 C15 119.9(3) . . ?
C21 N21 C11 125.2(2) . . ?
O21 C21 N21 123.1(3) . . ?
O21 C21 C22 122.1(3) . . ?
N21 C21 C22 114.7(2) . . ?
C23 C22 C21 115.0(3) . . ?
C22 C23 C23 113.9(3) . 3_564 ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.123
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.220

data_5I
_database_code_depnum_ccdc_archive 'CCDC 696962'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H26 I2 N2 O2'
_chemical_formula_weight         604.25

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'
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_H-M   P2(1)/c

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

_cell_length_a                   22.8808(17)
_cell_length_b                   4.7980(4)
_cell_length_c                   10.2227(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.371(2)
_cell_angle_gamma                90.00
_cell_volume                     1117.34(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2415
_cell_measurement_theta_min      0.89
_cell_measurement_theta_max      26.99

_exptl_crystal_description       Needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.796
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             588
_exptl_absorpt_coefficient_mu    2.834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.625
_exptl_absorpt_correction_T_max  0.715
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD APEX 2 BRUKER'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13932
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         0.89
_diffrn_reflns_theta_max         26.99
_reflns_number_total             2415
_reflns_number_gt                1977
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0580P)²+0.0000P] 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         2415
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0938
_refine_ls_wR_factor_gt          0.0781
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_restrained_S_all      1.145
_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
I1 I 0.056998(10) 0.69105(6) 0.17721(3) 0.05915(14) Uani 1 1 d . . .
N1 N 0.27230(13) 0.3221(5) -0.1199(3) 0.0422(6) Uani 1 1 d . . .
H1 H 0.2771 0.1460 -0.1303 0.051 Uiso 1 1 calc R . .
O1 O 0.31032(13) 0.7457(5) -0.1543(3) 0.0560(7) Uani 1 1 d . . .
C1 C 0.31057(13) 0.4948(6) -0.1719(3) 0.0368(6) Uani 1 1 d . . .
C2 C 0.35257(17) 0.3541(7) -0.2561(4) 0.0520(9) Uani 1 1 d . . .
H2A H 0.3739 0.2118 -0.2038 0.062 Uiso 1 1 calc . . .
H2B H 0.3298 0.2607 -0.3281 0.062 Uiso 1 1 calc . . .
C3 C 0.39591(15) 0.5393(7) -0.3121(4) 0.0501(8) Uani 1 1 d . . .
H3A H 0.4193 0.6307 -0.2405 0.060 Uiso 1 1 calc . . .
H3B H 0.3749 0.6828 -0.3641 0.060 Uiso 1 1 calc . . .
C4 C 0.43636(16) 0.3914(8) -0.3965(4) 0.0535(9) Uani 1 1 d . . .
H4A H 0.4127 0.2935 -0.4656 0.064 Uiso 1 1 calc . . .
H4B H 0.4582 0.2524 -0.3432 0.064 Uiso 1 1 calc . . .
C5 C 0.47940(15) 0.5744(8) -0.4590(4) 0.0557(9) Uani 1 1 d . . .
H5A H 0.4575 0.7108 -0.5139 0.067 Uiso 1 1 calc . . .
H5B H 0.5025 0.6754 -0.3901 0.067 Uiso 1 1 calc . . .
C11 C 0.22480(13) 0.4077(6) -0.0495(3) 0.0352(6) Uani 1 1 d . . .
C12 C 0.17133(17) 0.2763(7) -0.0775(4) 0.0480(8) Uani 1 1 d . . .
H12 H 0.1675 0.1362 -0.1406 0.058 Uiso 1 1 calc R . .
C13 C 0.12331(15) 0.3527(7) -0.0115(4) 0.0477(8) Uani 1 1 d . . .
H13 H 0.0873 0.2643 -0.0301 0.057 Uiso 1 1 calc R . .
C14 C 0.12958(12) 0.5610(7) 0.0817(3) 0.0385(7) Uani 1 1 d . . .
C15 C 0.18316(16) 0.6897(7) 0.1112(4) 0.0475(8) Uani 1 1 d . . .
H15 H 0.1872 0.8293 0.1745 0.057 Uiso 1 1 calc R . .
C16 C 0.23100(14) 0.6096(7) 0.0457(3) 0.0434(7) Uani 1 1 d . . .
H16 H 0.2673 0.6932 0.0665 0.052 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.04047(18) 0.0699(2) 0.0717(2) -0.00297(11) 0.02942(13) 0.00812(10)
N1 0.0427(15) 0.0285(12) 0.0599(17) -0.0051(11) 0.0288(13) 0.0007(10)
O1 0.0667(18) 0.0271(11) 0.0813(19) -0.0010(11) 0.0435(15) -0.0002(10)
C1 0.0356(15) 0.0330(15) 0.0445(16) 0.0014(12) 0.0176(13) 0.0023(12)
C2 0.054(2) 0.0377(16) 0.070(2) -0.0054(15) 0.0390(18) -0.0002(14)
C3 0.0455(18) 0.0452(18) 0.065(2) 0.0002(16) 0.0307(16) 0.0023(14)
C4 0.050(2) 0.0490(17) 0.067(2) -0.0018(17) 0.0351(18) 0.0020(16)
C5 0.051(2) 0.056(2) 0.066(2) -0.0013(18) 0.0350(18) 0.0023(17)
C11 0.0331(14) 0.0331(13) 0.0418(15) 0.0028(12) 0.0165(12) 0.0028(12)
C12 0.047(2) 0.0446(17) 0.056(2) -0.0129(15) 0.0197(17) -0.0072(15)
C13 0.0321(16) 0.053(2) 0.060(2) -0.0068(15) 0.0166(15) -0.0060(13)
C14 0.0309(14) 0.0444(16) 0.0431(16) 0.0048(13) 0.0179(13) 0.0053(12)
C15 0.0427(19) 0.055(2) 0.0474(19) -0.0133(15) 0.0160(15) 0.0002(14)
C16 0.0303(15) 0.0483(16) 0.0535(18) -0.0074(15) 0.0138(14) -0.0029(13)

_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 C14 2.098(3) . ?
N1 C1 1.350(4) . ?
N1 C11 1.419(3) . ?
O1 C1 1.217(4) . ?
C1 C2 1.509(4) . ?
C2 C3 1.485(4) . ?
C3 C4 1.502(4) . ?
C4 C5 1.506(5) . ?
C5 C5 1.499(6) 3_664 ?
C11 C16 1.371(5) . ?
C11 C12 1.382(5) . ?
C12 C13 1.391(5) . ?
C13 C14 1.379(5) . ?
C14 C15 1.380(5) . ?
C15 C16 1.390(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
C1 N1 C11 125.3(2) . . ?
O1 C1 N1 122.4(3) . . ?
O1 C1 C2 122.6(3) . . ?
N1 C1 C2 114.9(2) . . ?
C3 C2 C1 115.8(3) . . ?
C2 C3 C4 114.1(3) . . ?
C3 C4 C5 115.5(3) . . ?
C5 C5 C4 115.4(4) 3_664 . ?
C16 C11 C12 120.0(3) . . ?
C16 C11 N1 122.1(3) . . ?
C12 C11 N1 117.9(3) . . ?
C11 C12 C13 120.2(3) . . ?
C14 C13 C12 119.4(3) . . ?
C13 C14 C15 120.5(3) . . ?
C13 C14 I1 120.1(2) . . ?
C15 C14 I1 119.4(2) . . ?
C14 C15 C16 119.6(3) . . ?
C11 C16 C15 120.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.666
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.187

data_2Br
_database_code_depnum_ccdc_archive 'CCDC 696963'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 Br2 N2 O2'
_chemical_formula_weight         426.11

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   17.080(7)
_cell_length_b                   4.813(2)
_cell_length_c                   9.831(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.057(12)
_cell_angle_gamma                90.00
_cell_volume                     795.7(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1669
_cell_measurement_theta_min      1.21
_cell_measurement_theta_max      26.70

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.779
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_absorpt_coefficient_mu    5.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.484
_exptl_absorpt_correction_T_max  0.600
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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 APEX 2 BRuker'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9620
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.21
_diffrn_reflns_theta_max         26.70
_reflns_number_total             1669
_reflns_number_gt                1150
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1000P)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         1669
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1427
_refine_ls_wR_factor_gt          0.1186
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.42827(3) 0.66130(11) 0.14852(5) 0.0782(3) Uani 1 1 d . . .
N11 N 0.14023(18) 0.3517(5) -0.2765(3) 0.0417(7) Uani 1 1 d . . .
H11 H 0.1331 0.1777 -0.2944 0.050 Uiso 1 1 calc R . .
C11 C 0.20625(19) 0.4256(6) -0.1754(3) 0.0365(7) Uani 1 1 d . . .
C12 C 0.2774(2) 0.2865(8) -0.1728(4) 0.0540(10) Uani 1 1 d . . .
H12 H 0.2809 0.1455 -0.2361 0.065 Uiso 1 1 calc R . .
C13 C 0.3435(2) 0.3567(8) -0.0760(5) 0.0575(10) Uani 1 1 d . . .
H13 H 0.3914 0.2640 -0.0744 0.069 Uiso 1 1 calc R . .
C14 C 0.3378(2) 0.5612(8) 0.0161(4) 0.0462(8) Uani 1 1 d . . .
C15 C 0.2685(2) 0.6978(8) 0.0175(4) 0.0546(10) Uani 1 1 d . . .
H15 H 0.2657 0.8362 0.0825 0.066 Uiso 1 1 calc R . .
C16 C 0.2018(2) 0.6291(7) -0.0790(4) 0.0482(9) Uani 1 1 d . . .
H16 H 0.1540 0.7211 -0.0784 0.058 Uiso 1 1 calc R . .
O21 O 0.08887(16) 0.7796(5) -0.3257(3) 0.0511(7) Uani 1 1 d . . .
C21 C 0.08730(18) 0.5305(6) -0.3475(3) 0.0358(7) Uani 1 1 d . . .
C22 C 0.0271(2) 0.3981(6) -0.4585(4) 0.0464(9) Uani 1 1 d . . .
H22A H -0.0045 0.2674 -0.4160 0.056 Uiso 1 1 calc . . .
H22B H 0.0549 0.2941 -0.5200 0.056 Uiso 1 1 calc . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0457(4) 0.1063(5) 0.0695(4) -0.0055(2) -0.0259(2) -0.0133(2)
N11 0.0412(16) 0.0288(12) 0.0468(16) -0.0015(10) -0.0153(13) -0.0042(10)
C11 0.0345(18) 0.0347(14) 0.0355(16) 0.0033(13) -0.0075(14) -0.0035(12)
C12 0.047(2) 0.0545(19) 0.054(2) -0.0142(17) -0.0114(18) 0.0125(16)
C13 0.035(2) 0.071(2) 0.061(2) -0.0001(19) -0.0071(18) 0.0085(17)
C14 0.0324(18) 0.0601(19) 0.0405(18) 0.0020(16) -0.0096(14) -0.0078(15)
C15 0.045(2) 0.066(2) 0.045(2) -0.0171(17) -0.0116(17) 0.0009(17)
C16 0.036(2) 0.0587(19) 0.046(2) -0.0119(16) -0.0041(16) 0.0038(15)
O21 0.0577(17) 0.0286(11) 0.0561(16) -0.0026(10) -0.0203(13) -0.0030(10)
C21 0.0348(18) 0.0322(15) 0.0361(16) -0.0003(12) -0.0061(13) -0.0057(13)
C22 0.044(2) 0.0331(14) 0.052(2) -0.0019(14) -0.0206(16) -0.0072(14)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C14 1.900(3) . ?
N11 C21 1.351(4) . ?
N11 C11 1.412(4) . ?
C11 C16 1.373(5) . ?
C11 C12 1.384(5) . ?
C12 C13 1.385(6) . ?
C13 C14 1.352(5) . ?
C14 C15 1.356(6) . ?
C15 C16 1.390(5) . ?
O21 C21 1.218(4) . ?
C21 C22 1.504(4) . ?
C22 C22 1.490(7) 3_564 ?

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
C21 N11 C11 125.7(2) . . ?
C16 C11 C12 119.1(3) . . ?
C16 C11 N11 122.1(3) . . ?
C12 C11 N11 118.8(3) . . ?
C13 C12 C11 120.1(3) . . ?
C14 C13 C12 119.5(4) . . ?
C15 C14 C13 121.6(3) . . ?
C15 C14 Br1 118.5(3) . . ?
C13 C14 Br1 119.9(3) . . ?
C14 C15 C16 119.4(3) . . ?
C11 C16 C15 120.2(3) . . ?
O21 C21 N11 122.9(3) . . ?
O21 C21 C22 122.4(3) . . ?
N11 C21 C22 114.6(3) . . ?
C21 C22 C22 113.5(3) . 3_564 ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        26.70
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.655
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.084

data_3Br
_database_code_depnum_ccdc_archive 'CCDC 696964'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 Br2 N2 O2'
_chemical_formula_weight         454.16

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   4.9461(5)
_cell_length_b                   8.6603(9)
_cell_length_c                   10.7293(11)
_cell_angle_alpha                90.812(3)
_cell_angle_beta                 100.267(3)
_cell_angle_gamma                96.325(3)
_cell_volume                     449.21(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1896
_cell_measurement_theta_min      1.93
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             226
_exptl_absorpt_coefficient_mu    4.524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.448
_exptl_absorpt_correction_T_max  0.585
_exptl_absorpt_process_details   SADASB

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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 APEX 2 Bruker'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5915
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         27.00
_reflns_number_total             1896
_reflns_number_gt                1475
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0796P)²+0.2034P] 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       0.052(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1896
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1341
_refine_ls_wR_factor_gt          0.1258
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.24585(10) 0.10786(5) 0.89001(3) 0.0831(3) Uani 1 1 d . . .
N11 N -0.1102(5) 0.3002(3) 0.3494(2) 0.0445(6) Uani 1 1 d . . .
H11 H -0.2846 0.3029 0.3242 0.053 Uiso 1 1 calc R . .
C11 C -0.0242(5) 0.2602(3) 0.4762(3) 0.0389(6) Uani 1 1 d . . .
C12 C -0.1858(8) 0.1492(7) 0.5287(4) 0.0807(15) Uani 1 1 d . . .
H12 H -0.3503 0.1027 0.4804 0.097 Uiso 1 1 calc R . .
C13 C -0.1083(10) 0.1058(6) 0.6515(4) 0.0824(14) Uani 1 1 d . . .
H13 H -0.2198 0.0305 0.6858 0.099 Uiso 1 1 calc R . .
C14 C 0.1314(7) 0.1733(4) 0.7225(3) 0.0494(7) Uani 1 1 d . . .
C15 C 0.2895(8) 0.2848(5) 0.6739(4) 0.0681(11) Uani 1 1 d . . .
H15 H 0.4515 0.3324 0.7236 0.082 Uiso 1 1 calc R . .
C16 C 0.2131(8) 0.3289(4) 0.5510(3) 0.0612(9) Uani 1 1 d . . .
H16 H 0.3241 0.4062 0.5185 0.073 Uiso 1 1 calc R . .
O21 O 0.3049(4) 0.3331(4) 0.2897(3) 0.0734(9) Uani 1 1 d . . .
C21 C 0.0546(6) 0.3346(4) 0.2643(3) 0.0449(7) Uani 1 1 d . . .
C22 C -0.0924(6) 0.3678(5) 0.1333(3) 0.0531(8) Uani 1 1 d . . .
H22A H -0.1324 0.2717 0.0825 0.064 Uiso 1 1 calc . . .
H22B H -0.2674 0.4051 0.1399 0.064 Uiso 1 1 calc . . .
C23 C 0.0727(5) 0.4862(4) 0.0668(3) 0.0437(7) Uani 1 1 d . . .
H23A H 0.2506 0.4509 0.0631 0.052 Uiso 1 1 calc . . .
H23B H 0.1062 0.5837 0.1157 0.052 Uiso 1 1 calc . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.1158(5) 0.0929(4) 0.0397(3) 0.0186(2) 0.0008(2) 0.0272(3)
N11 0.0239(10) 0.0664(16) 0.0422(14) 0.0168(11) 0.0015(9) 0.0067(10)
C11 0.0314(13) 0.0487(15) 0.0371(14) 0.0102(12) 0.0050(11) 0.0080(11)
C12 0.052(2) 0.123(4) 0.053(2) 0.034(2) -0.0067(17) -0.030(2)
C13 0.077(3) 0.107(3) 0.055(2) 0.038(2) 0.005(2) -0.021(2)
C14 0.0604(19) 0.0540(17) 0.0342(15) 0.0079(13) 0.0039(13) 0.0157(14)
C15 0.064(2) 0.080(3) 0.046(2) 0.0068(18) -0.0131(16) -0.0155(19)
C16 0.062(2) 0.067(2) 0.0439(19) 0.0137(16) -0.0038(15) -0.0200(17)
O21 0.0230(10) 0.141(3) 0.0571(16) 0.0414(16) 0.0051(10) 0.0132(12)
C21 0.0295(14) 0.0662(18) 0.0384(16) 0.0193(13) 0.0031(11) 0.0052(12)
C22 0.0318(14) 0.082(2) 0.0415(17) 0.0224(15) -0.0025(12) 0.0011(14)
C23 0.0329(14) 0.0590(18) 0.0362(16) 0.0116(13) -0.0011(11) 0.0019(12)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C14 1.900(3) . ?
N11 C21 1.344(4) . ?
N11 C11 1.411(4) . ?
C11 C16 1.369(4) . ?
C11 C12 1.373(5) . ?
C12 C13 1.375(6) . ?
C13 C14 1.356(6) . ?
C14 C15 1.345(5) . ?
C15 C16 1.377(5) . ?
O21 C21 1.221(4) . ?
C21 C22 1.510(4) . ?
C22 C23 1.507(4) . ?
C23 C23 1.520(5) 2_565 ?

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
C21 N11 C11 126.2(2) . . ?
C16 C11 C12 117.9(3) . . ?
C16 C11 N11 122.9(3) . . ?
C12 C11 N11 119.2(3) . . ?
C13 C12 C11 121.1(3) . . ?
C14 C13 C12 119.8(4) . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 Br1 120.1(3) . . ?
C13 C14 Br1 119.8(3) . . ?
C14 C15 C16 120.4(3) . . ?
C15 C16 C11 120.7(3) . . ?
O21 C21 N11 122.3(3) . . ?
O21 C21 C22 122.2(3) . . ?
N11 C21 C22 115.4(2) . . ?
C23 C22 C21 113.1(2) . . ?
C22 C23 C23 112.6(3) . 2_565 ?

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         0.771
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.075

data_4Br
_database_code_depnum_ccdc_archive 'CCDC 696965'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 Br2 N2 O2'
_chemical_formula_weight         482.22

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   22.113(3)
_cell_length_b                   5.1003(7)
_cell_length_c                   17.945(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.259(4)
_cell_angle_gamma                90.00
_cell_volume                     1942.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2134
_cell_measurement_theta_min      1.92
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    4.189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.580
_exptl_absorpt_correction_T_max  0.688
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD APEX 2 Bruker'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12286
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         27.00
_reflns_number_total             2134
_reflns_number_gt                1577
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0471P)²+0.7066P] 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         2134
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0838
_refine_ls_wR_factor_gt          0.0781
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.059513(13) 0.84577(7) 0.206437(18) 0.07735(16) Uani 1 1 d . . .
O1 O 0.32070(8) 1.1498(3) 0.09292(11) 0.0529(4) Uani 1 1 d . . .
N1 N 0.29745(8) 0.7236(3) 0.10520(10) 0.0373(4) Uani 1 1 d . . .
H1 H 0.3093 0.5660 0.0997 0.045 Uiso 1 1 calc R . .
C1 C 0.33558(10) 0.9199(4) 0.09461(12) 0.0353(4) Uani 1 1 d . . .
C2 C 0.39875(10) 0.8315(4) 0.08721(13) 0.0410(5) Uani 1 1 d . . .
H2A H 0.3950 0.6532 0.0677 0.049 Uiso 1 1 calc . . .
H2B H 0.4288 0.8311 0.1383 0.049 Uiso 1 1 calc . . .
C3 C 0.42357(10) 1.0035(4) 0.03389(13) 0.0397(5) Uani 1 1 d . . .
H3A H 0.4279 1.1813 0.0538 0.048 Uiso 1 1 calc . . .
H3B H 0.3932 1.0060 -0.0170 0.048 Uiso 1 1 calc . . .
C4 C 0.48668(10) 0.9113(4) 0.02570(14) 0.0421(5) Uani 1 1 d . . .
H4A H 0.4819 0.7357 0.0041 0.051 Uiso 1 1 calc . . .
H4B H 0.5166 0.9025 0.0768 0.051 Uiso 1 1 calc . . .
C11 C 0.24022(9) 0.7529(4) 0.12440(11) 0.0320(4) Uani 1 1 d . . .
C12 C 0.19819(9) 0.9553(4) 0.09586(12) 0.0389(5) Uani 1 1 d . . .
H12 H 0.2063 1.0750 0.0607 0.047 Uiso 1 1 calc R . .
C13 C 0.14430(10) 0.9778(4) 0.11993(13) 0.0436(5) Uani 1 1 d . . .
H13 H 0.1162 1.1141 0.1013 0.052 Uiso 1 1 calc R . .
C14 C 0.13202(10) 0.8008(4) 0.17103(13) 0.0405(5) Uani 1 1 d . . .
C16 C 0.22588(10) 0.5701(4) 0.17429(12) 0.0384(5) Uani 1 1 d . . .
H16 H 0.2531 0.4302 0.1921 0.046 Uiso 1 1 calc R . .
C15 C 0.17176(11) 0.5940(4) 0.19765(12) 0.0431(5) Uani 1 1 d . . .
H15 H 0.1624 0.4712 0.2311 0.052 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.05043(19) 0.1094(3) 0.0885(3) -0.00672(17) 0.04616(16) 0.00350(15)
O1 0.0483(9) 0.0273(8) 0.0958(13) 0.0021(7) 0.0410(9) 0.0037(6)
N1 0.0364(9) 0.0250(8) 0.0577(11) 0.0015(7) 0.0248(8) 0.0041(7)
C1 0.0340(10) 0.0312(11) 0.0469(11) 0.0004(9) 0.0213(9) 0.0000(8)
C2 0.0370(11) 0.0363(11) 0.0569(13) 0.0052(9) 0.0251(10) 0.0061(9)
C3 0.0318(10) 0.0361(11) 0.0574(13) 0.0036(9) 0.0225(9) 0.0026(9)
C4 0.0348(11) 0.0384(11) 0.0605(13) 0.0024(10) 0.0255(10) 0.0029(9)
C11 0.0299(10) 0.0292(9) 0.0402(10) -0.0045(8) 0.0150(8) -0.0024(8)
C12 0.0351(11) 0.0349(10) 0.0494(12) 0.0055(9) 0.0164(9) 0.0013(9)
C13 0.0329(10) 0.0388(11) 0.0604(14) 0.0017(10) 0.0154(10) 0.0065(9)
C14 0.0305(10) 0.0500(13) 0.0459(11) -0.0084(10) 0.0188(9) -0.0039(9)
C16 0.0372(11) 0.0324(10) 0.0469(11) 0.0053(9) 0.0142(9) 0.0020(9)
C15 0.0423(12) 0.0488(12) 0.0424(11) 0.0037(9) 0.0189(9) -0.0076(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
Br1 C14 1.897(2) . ?
O1 C1 1.216(2) . ?
N1 C1 1.356(3) . ?
N1 C11 1.410(3) . ?
C1 C2 1.509(3) . ?
C2 C3 1.510(3) . ?
C3 C4 1.518(3) . ?
C4 C4 1.523(4) 5_675 ?
C11 C12 1.387(3) . ?
C11 C16 1.389(3) . ?
C12 C13 1.381(3) . ?
C13 C14 1.367(3) . ?
C14 C15 1.370(3) . ?
C16 C15 1.380(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C11 126.29(17) . . ?
O1 C1 N1 122.76(19) . . ?
O1 C1 C2 122.47(18) . . ?
N1 C1 C2 114.76(17) . . ?
C1 C2 C3 113.07(17) . . ?
C2 C3 C4 112.87(17) . . ?
C3 C4 C4 113.4(2) . 5_675 ?
C12 C11 C16 119.14(19) . . ?
C12 C11 N1 122.89(18) . . ?
C16 C11 N1 117.97(18) . . ?
C13 C12 C11 119.59(19) . . ?
C14 C13 C12 120.4(2) . . ?
C13 C14 C15 120.9(2) . . ?
C13 C14 Br1 119.34(16) . . ?
C15 C14 Br1 119.74(16) . . ?
C15 C16 C11 120.7(2) . . ?
C14 C15 C16 119.2(2) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.058

data_2Cl
_database_code_depnum_ccdc_archive 'CCDC 696966'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 Cl2 N2 O2'
_chemical_formula_weight         337.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   8.4189(6)
_cell_length_b                   9.4168(6)
_cell_length_c                   9.7128(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.498(2)
_cell_angle_gamma                90.00
_cell_volume                     769.29(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1658
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      26.99

_exptl_crystal_description       Needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    0.430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_T_max  0.956
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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 APEX 2 Bruker'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9829
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0157
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.42
_diffrn_reflns_theta_max         26.99
_reflns_number_total             1658
_reflns_number_gt                1514
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1000P)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     SHELXL
_refine_ls_extinction_coef       0.066(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1658
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1643
_refine_ls_wR_factor_gt          0.1606
_refine_ls_goodness_of_fit_ref   1.485
_refine_ls_restrained_S_all      1.485
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001

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
Cl1 Cl 0.94019(5) 0.15775(5) 0.41447(5) 0.0620(3) Uani 1 1 d . . .
N11 N 0.64819(13) 0.70904(13) 0.54699(11) 0.0335(4) Uani 1 1 d . . .
H11 H 0.6385 0.7201 0.6341 0.040 Uiso 1 1 calc R . .
C11 C 0.71401(14) 0.57884(14) 0.50570(13) 0.0305(4) Uani 1 1 d . . .
C12 C 0.69423(17) 0.46249(17) 0.59121(14) 0.0379(4) Uani 1 1 d . . .
H12 H 0.6344 0.4720 0.6689 0.045 Uiso 1 1 calc R . .
C13 C 0.76195(18) 0.33321(17) 0.56260(17) 0.0414(4) Uani 1 1 d . . .
H13 H 0.7487 0.2558 0.6205 0.050 Uiso 1 1 calc R . .
C14 C 0.85006(16) 0.32061(17) 0.44614(16) 0.0385(4) Uani 1 1 d . . .
C15 C 0.87036(17) 0.43334(17) 0.35950(15) 0.0400(4) Uani 1 1 d . . .
H15 H 0.9293 0.4224 0.2814 0.048 Uiso 1 1 calc R . .
C16 C 0.80287(17) 0.56386(17) 0.38846(14) 0.0362(4) Uani 1 1 d . . .
H16 H 0.8167 0.6408 0.3302 0.043 Uiso 1 1 calc R . .
O21 O 0.60447(16) 0.81761(13) 0.34081(11) 0.0506(4) Uani 1 1 d . . .
C21 C 0.59865(16) 0.81822(16) 0.46617(13) 0.0334(4) Uani 1 1 d . . .
C22 C 0.5316(2) 0.94103(17) 0.54540(14) 0.0433(4) Uani 1 1 d . . .
H22A H 0.4466 0.9062 0.6006 0.052 Uiso 1 1 calc . . .
H22B H 0.6143 0.9786 0.6078 0.052 Uiso 1 1 calc . . .

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
Cl1 0.0741(4) 0.0411(4) 0.0711(5) -0.00947(19) 0.0076(3) 0.02214(19)
N11 0.0479(6) 0.0313(7) 0.0219(6) 0.0008(4) 0.0066(4) 0.0071(5)
C11 0.0342(6) 0.0303(8) 0.0270(7) -0.0006(5) 0.0017(5) 0.0023(5)
C12 0.0469(7) 0.0365(8) 0.0310(7) 0.0044(6) 0.0108(5) 0.0039(6)
C13 0.0519(8) 0.0318(9) 0.0408(9) 0.0036(6) 0.0041(6) 0.0026(6)
C14 0.0394(7) 0.0329(8) 0.0431(9) -0.0069(6) -0.0009(6) 0.0058(5)
C15 0.0415(7) 0.0443(9) 0.0348(8) -0.0057(6) 0.0085(5) 0.0053(6)
C16 0.0432(7) 0.0356(8) 0.0303(7) 0.0042(5) 0.0086(5) 0.0034(5)
O21 0.0896(9) 0.0397(7) 0.0236(6) 0.0044(4) 0.0133(5) 0.0188(6)
C21 0.0474(8) 0.0295(7) 0.0237(7) 0.0012(5) 0.0051(5) 0.0030(5)
C22 0.0682(10) 0.0353(8) 0.0269(8) -0.0005(6) 0.0070(6) 0.0137(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
Cl1 C14 1.7444(15) . ?
N11 C21 1.3486(18) . ?
N11 C11 1.4108(17) . ?
C11 C12 1.3893(19) . ?
C11 C16 1.3966(19) . ?
C12 C13 1.378(2) . ?
C13 C14 1.385(2) . ?
C14 C15 1.370(2) . ?
C15 C16 1.388(2) . ?
O21 C21 1.2208(17) . ?
C21 C22 1.512(2) . ?
C22 C22 1.501(3) 3_676 ?

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
C21 N11 C11 127.76(12) . . ?
C12 C11 C16 119.35(13) . . ?
C12 C11 N11 117.17(12) . . ?
C16 C11 N11 123.41(12) . . ?
C13 C12 C11 120.99(13) . . ?
C12 C13 C14 118.79(14) . . ?
C15 C14 C13 121.40(14) . . ?
C15 C14 Cl1 120.40(12) . . ?
C13 C14 Cl1 118.17(12) . . ?
C14 C15 C16 119.90(13) . . ?
C15 C16 C11 119.56(13) . . ?
O21 C21 N11 123.52(13) . . ?
O21 C21 C22 122.91(13) . . ?
N11 C21 C22 113.56(11) . . ?
C22 C22 C21 113.42(15) 3_676 . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.056

data_3Cl
_database_code_depnum_ccdc_archive 'CCDC 696967'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 Cl2 N2 O2'
_chemical_formula_weight         365.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   8.2555(7)
_cell_length_b                   10.9653(9)
_cell_length_c                   9.4726(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.294(2)
_cell_angle_gamma                90.00
_cell_volume                     852.33(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1854
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      26.98

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    0.394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      243(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 APEX 2 BRuker'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11032
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         26.98
_reflns_number_total             1854
_reflns_number_gt                1749
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0490P)²+0.3105P] 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         1854
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0845
_refine_ls_wR_factor_gt          0.0833
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.002

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
Cl1 Cl 0.07972(4) 0.14205(3) 0.02237(3) 0.02784(13) Uani 1 1 d . . .
O17 O 0.31163(11) 0.72135(8) -0.12688(9) 0.0236(2) Uani 1 1 d . . .
N11 N 0.29351(13) 0.65610(9) 0.09911(10) 0.0183(2) Uani 1 1 d . . .
H11 H 0.3062 0.6785 0.1866 0.022 Uiso 1 1 calc R . .
C11 C 0.23944(13) 0.53498(10) 0.07175(11) 0.0162(2) Uani 1 1 d . . .
C12 C 0.28972(14) 0.46495(11) -0.03854(12) 0.0194(2) Uani 1 1 d . . .
H12 H 0.3565 0.4990 -0.1010 0.023 Uiso 1 1 calc R . .
C13 C 0.23975(15) 0.34417(11) -0.05480(13) 0.0207(3) Uani 1 1 d . . .
H13 H 0.2729 0.2969 -0.1279 0.025 Uiso 1 1 calc R . .
C14 C 0.13987(14) 0.29487(11) 0.03926(12) 0.0193(2) Uani 1 1 d . . .
C15 C 0.08659(15) 0.36358(10) 0.14756(13) 0.0200(3) Uani 1 1 d . . .
H15 H 0.0182 0.3296 0.2087 0.024 Uiso 1 1 calc R . .
C16 C 0.13684(14) 0.48396(11) 0.16355(12) 0.0180(2) Uani 1 1 d . . .
H16 H 0.1019 0.5311 0.2360 0.022 Uiso 1 1 calc R . .
C17 C 0.32737(13) 0.74052(10) 0.00191(12) 0.0176(2) Uani 1 1 d . . .
C18 C 0.38554(15) 0.86132(10) 0.06609(13) 0.0204(3) Uani 1 1 d . . .
H18A H 0.4634 0.8459 0.1485 0.025 Uiso 1 1 calc . . .
H18B H 0.2935 0.9040 0.0983 0.025 Uiso 1 1 calc . . .
C19 C 0.46458(15) 0.94267(10) -0.03634(12) 0.0193(2) Uani 1 1 d . . .
H19A H 0.3841 0.9653 -0.1143 0.023 Uiso 1 1 calc . . .
H19B H 0.5506 0.8979 -0.0754 0.023 Uiso 1 1 calc . . .

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
Cl1 0.0392(2) 0.01335(18) 0.0314(2) -0.00214(10) 0.00617(14) -0.00786(11)
O17 0.0392(5) 0.0176(4) 0.0141(4) -0.0002(3) 0.0039(3) -0.0068(4)
N11 0.0286(5) 0.0136(5) 0.0127(4) -0.0013(3) 0.0027(4) -0.0044(4)
C11 0.0209(5) 0.0121(5) 0.0151(5) 0.0014(4) -0.0007(4) -0.0015(4)
C12 0.0235(5) 0.0172(6) 0.0183(5) -0.0002(4) 0.0054(4) -0.0028(4)
C13 0.0257(6) 0.0164(6) 0.0203(6) -0.0037(4) 0.0042(4) 0.0001(4)
C14 0.0230(5) 0.0114(5) 0.0228(6) 0.0005(4) -0.0009(4) -0.0030(4)
C15 0.0239(6) 0.0186(6) 0.0175(6) 0.0026(4) 0.0026(4) -0.0043(4)
C16 0.0226(5) 0.0171(6) 0.0145(5) -0.0007(4) 0.0025(4) -0.0007(4)
C17 0.0214(5) 0.0144(5) 0.0172(5) 0.0001(4) 0.0032(4) -0.0021(4)
C18 0.0305(6) 0.0143(6) 0.0170(5) -0.0020(4) 0.0051(5) -0.0057(4)
C19 0.0264(6) 0.0149(6) 0.0163(5) 0.0004(4) 0.0020(4) -0.0059(4)

_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
Cl1 C14 1.7500(12) . ?
O17 C17 1.2306(14) . ?
N11 C17 1.3562(14) . ?
N11 C11 1.4159(14) . ?
C11 C12 1.3960(16) . ?
C11 C16 1.3958(15) . ?
C12 C13 1.3906(16) . ?
C13 C14 1.3882(17) . ?
C14 C15 1.3830(17) . ?
C15 C16 1.3869(16) . ?
C17 C18 1.5136(15) . ?
C18 C19 1.5172(16) . ?
C19 C19 1.519(2) 3_675 ?

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
C17 N11 C11 126.89(10) . . ?
C12 C11 C16 119.76(10) . . ?
C12 C11 N11 122.64(10) . . ?
C16 C11 N11 117.56(10) . . ?
C13 C12 C11 119.86(11) . . ?
C14 C13 C12 119.32(11) . . ?
C15 C14 C13 121.57(11) . . ?
C15 C14 Cl1 118.65(9) . . ?
C13 C14 Cl1 119.78(9) . . ?
C14 C15 C16 118.94(11) . . ?
C15 C16 C11 120.54(11) . . ?
O17 C17 N11 123.31(10) . . ?
O17 C17 C18 122.82(10) . . ?
N11 C17 C18 113.86(9) . . ?
C17 C18 C19 113.42(9) . . ?
C18 C19 C19 111.59(12) . 3_675 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.98
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.113

data_4Cl
_database_code_depnum_ccdc_archive 'CCDC 696968'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 Cl2 N2 O2'
_chemical_formula_weight         393.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   21.870(8)
_cell_length_b                   5.1043(19)
_cell_length_c                   17.683(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.685(10)
_cell_angle_gamma                90.00
_cell_volume                     1900.5(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2061
_cell_measurement_theta_min      1.93
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD APEX 2 Bruker'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12186
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         27.00
_reflns_number_total             2061
_reflns_number_gt                1727
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0618P)²+0.6333P] 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         2061
_refine_ls_number_parameters     118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.1063
_refine_ls_wR_factor_gt          0.1022
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
Cl1 Cl 0.05935(2) 0.83589(11) 0.20576(3) 0.0766(2) Uani 1 1 d . . .
N11 N 0.29460(5) 0.7241(2) 0.10598(7) 0.0364(3) Uani 1 1 d . . .
H11 H 0.3066 0.5668 0.1001 0.044 Uiso 1 1 calc R . .
C11 C 0.23668(6) 0.7534(2) 0.12582(7) 0.0317(3) Uani 1 1 d . . .
C12 C 0.19462(6) 0.9561(3) 0.09743(8) 0.0386(3) Uani 1 1 d . . .
H12 H 0.2032 1.0768 0.0622 0.046 Uiso 1 1 calc R . .
C13 C 0.13992(6) 0.9780(3) 0.12171(9) 0.0447(3) Uani 1 1 d . . .
H13 H 0.1117 1.1145 0.1031 0.054 Uiso 1 1 calc R . .
C14 C 0.12714(6) 0.7984(3) 0.17329(9) 0.0429(3) Uani 1 1 d . . .
C15 C 0.16714(7) 0.5908(3) 0.19961(8) 0.0423(3) Uani 1 1 d . . .
H15 H 0.1574 0.4666 0.2330 0.051 Uiso 1 1 calc R . .
C16 C 0.22198(6) 0.5691(3) 0.17586(8) 0.0379(3) Uani 1 1 d . . .
H16 H 0.2494 0.4295 0.1936 0.046 Uiso 1 1 calc R . .
O21 O 0.31806(5) 1.15126(18) 0.09388(7) 0.0505(3) Uani 1 1 d . . .
C21 C 0.33299(6) 0.9207(2) 0.09534(8) 0.0347(3) Uani 1 1 d . . .
C22 C 0.39706(7) 0.8333(3) 0.08829(9) 0.0407(3) Uani 1 1 d . . .
H22A H 0.3937 0.6551 0.0685 0.049 Uiso 1 1 calc . . .
H22B H 0.4269 0.8331 0.1401 0.049 Uiso 1 1 calc . . .
C23 C 0.42274(6) 1.0057(3) 0.03458(9) 0.0396(3) Uani 1 1 d . . .
H23A H 0.4271 1.1832 0.0549 0.047 Uiso 1 1 calc . . .
H23B H 0.3926 1.0090 -0.0169 0.047 Uiso 1 1 calc . . .
C24 C 0.48658(6) 0.9133(3) 0.02645(9) 0.0415(3) Uani 1 1 d . . .
H24A H 0.5165 0.9074 0.0781 0.050 Uiso 1 1 calc . . .
H24B H 0.4821 0.7365 0.0055 0.050 Uiso 1 1 calc . . .

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
Cl1 0.0505(3) 0.1016(4) 0.0937(4) -0.0086(3) 0.0469(3) 0.0013(2)
N11 0.0365(6) 0.0258(5) 0.0531(7) 0.0005(4) 0.0229(5) 0.0038(4)
C11 0.0317(6) 0.0289(6) 0.0372(6) -0.0043(5) 0.0140(5) -0.0017(5)
C12 0.0349(7) 0.0337(6) 0.0495(8) 0.0048(6) 0.0152(6) 0.0014(5)
C13 0.0330(7) 0.0405(7) 0.0618(9) -0.0002(6) 0.0149(6) 0.0054(6)
C14 0.0334(7) 0.0519(8) 0.0483(8) -0.0110(6) 0.0195(6) -0.0054(6)
C15 0.0433(8) 0.0478(8) 0.0400(7) 0.0021(6) 0.0186(6) -0.0071(6)
C16 0.0388(7) 0.0341(6) 0.0422(7) 0.0028(5) 0.0132(6) 0.0001(5)
O21 0.0466(6) 0.0282(5) 0.0887(8) 0.0026(5) 0.0391(6) 0.0031(4)
C21 0.0356(7) 0.0312(6) 0.0422(7) 0.0014(5) 0.0190(5) 0.0034(5)
C22 0.0363(7) 0.0381(7) 0.0540(8) 0.0068(6) 0.0229(6) 0.0075(6)
C23 0.0339(6) 0.0358(7) 0.0549(8) 0.0034(6) 0.0220(6) 0.0036(5)
C24 0.0327(7) 0.0382(7) 0.0591(9) 0.0027(6) 0.0222(6) 0.0045(5)

_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
Cl1 C14 1.7391(15) . ?
N11 C21 1.3537(17) . ?
N11 C11 1.4106(17) . ?
C11 C16 1.3874(18) . ?
C11 C12 1.3854(18) . ?
C12 C13 1.3804(19) . ?
C13 C14 1.374(2) . ?
C14 C15 1.373(2) . ?
C15 C16 1.3783(19) . ?
O21 C21 1.2196(16) . ?
C21 C22 1.5074(18) . ?
C22 C23 1.5102(19) . ?
C23 C24 1.5170(18) . ?
C24 C24 1.517(3) 5_675 ?

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
C21 N11 C11 126.05(11) . . ?
C16 C11 C12 119.46(12) . . ?
C16 C11 N11 117.73(11) . . ?
C12 C11 N11 122.81(12) . . ?
C13 C12 C11 119.61(13) . . ?
C12 C13 C14 120.09(13) . . ?
C15 C14 C13 120.97(13) . . ?
C15 C14 Cl1 119.68(12) . . ?
C13 C14 Cl1 119.35(12) . . ?
C14 C15 C16 119.09(13) . . ?
C15 C16 C11 120.71(13) . . ?
O21 C21 N11 123.07(13) . . ?
O21 C21 C22 122.23(12) . . ?
N11 C21 C22 114.67(11) . . ?
C21 C22 C23 113.06(11) . . ?
C22 C23 C24 112.75(11) . . ?
C24 C24 C23 113.35(14) 5_675 . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.062

data_2F
_database_code_depnum_ccdc_archive 'CCDC 696969'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 F2 N2 O2'
_chemical_formula_weight         304.29

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   7.7199(4)
_cell_length_b                   5.7814(3)
_cell_length_c                   32.4814(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.019(2)
_cell_angle_gamma                90.00
_cell_volume                     1446.14(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3446
_cell_measurement_theta_min      1.26
_cell_measurement_theta_max      27.99

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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 APEX 2 Bruker'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18570
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         1.26
_diffrn_reflns_theta_max         27.99
_reflns_number_total             3446
_reflns_number_gt                2440
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0980P)²+0.2928P] 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         3446
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1817
_refine_ls_wR_factor_gt          0.1670
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.004

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
F14 F 0.05746(18) 0.3264(3) 0.23652(3) 0.0826(4) Uani 1 1 d . . .
F24 F 0.46221(19) 1.1458(3) -0.23624(4) 0.0862(4) Uani 1 1 d . . .
N11 N 0.23257(17) 0.4758(2) 0.07720(4) 0.0497(4) Uani 1 1 d . . .
H11 H 0.3174 0.3912 0.0703 0.060 Uiso 1 1 calc R . .
C11 C 0.17799(19) 0.4398(3) 0.11748(4) 0.0427(4) Uani 1 1 d . . .
C12 C 0.2293(2) 0.2366(3) 0.13749(5) 0.0529(4) Uani 1 1 d . . .
H12 H 0.2907 0.1256 0.1238 0.063 Uiso 1 1 calc R . .
C13 C 0.1897(2) 0.1986(3) 0.17755(6) 0.0584(5) Uani 1 1 d . . .
H13 H 0.2240 0.0628 0.1911 0.070 Uiso 1 1 calc R . .
C14 C 0.0984(2) 0.3647(3) 0.19718(5) 0.0549(4) Uani 1 1 d . . .
C15 C 0.0459(2) 0.5664(3) 0.17834(5) 0.0536(4) Uani 1 1 d . . .
H15 H -0.0162 0.6757 0.1923 0.064 Uiso 1 1 calc R . .
C16 C 0.0866(2) 0.6049(3) 0.13811(5) 0.0480(4) Uani 1 1 d . . .
H16 H 0.0527 0.7419 0.1249 0.058 Uiso 1 1 calc R . .
N21 N 0.25962(18) 1.0228(3) -0.07838(4) 0.0548(4) Uani 1 1 d . . .
H21 H 0.1772 1.1096 -0.0708 0.066 Uiso 1 1 calc R . .
C21 C 0.31582(19) 1.0538(3) -0.11914(5) 0.0456(4) Uani 1 1 d . . .
C22 C 0.3993(2) 1.2551(3) -0.12938(6) 0.0573(4) Uani 1 1 d . . .
H22 H 0.4220 1.3695 -0.1096 0.069 Uiso 1 1 calc R . .
C23 C 0.4490(2) 1.2857(3) -0.16905(6) 0.0621(5) Uani 1 1 d . . .
H23 H 0.5064 1.4197 -0.1762 0.074 Uiso 1 1 calc R . .
C24 C 0.4123(2) 1.1160(3) -0.19748(5) 0.0562(4) Uani 1 1 d . . .
C25 C 0.3294(3) 0.9165(3) -0.18827(5) 0.0591(5) Uani 1 1 d . . .
H25 H 0.3063 0.8035 -0.2083 0.071 Uiso 1 1 calc R . .
C26 C 0.2804(2) 0.8859(3) -0.14854(5) 0.0537(4) Uani 1 1 d . . .
H26 H 0.2233 0.7512 -0.1416 0.064 Uiso 1 1 calc R . .
O31 O 0.0397(3) 0.7408(4) 0.05313(5) 0.1287(9) Uani 1 1 d . . .
O34 O 0.4503(2) 0.7470(3) -0.05911(4) 0.0910(6) Uani 1 1 d . . .
C31 C 0.1688(3) 0.6242(4) 0.04894(6) 0.0697(6) Uani 1 1 d . . .
C32 C 0.2649(3) 0.6360(4) 0.01002(6) 0.0824(8) Uani 1 1 d . . .
H32A H 0.3877 0.6118 0.0171 0.099 Uiso 1 1 calc . . .
H32B H 0.2245 0.5120 -0.0083 0.099 Uiso 1 1 calc . . .
C33 C 0.2416(3) 0.8561(4) -0.01163(6) 0.0784(7) Uani 1 1 d . . .
H33A H 0.2880 0.9786 0.0063 0.094 Uiso 1 1 calc . . .
H33B H 0.1182 0.8842 -0.0170 0.094 Uiso 1 1 calc . . .
C34 C 0.3269(2) 0.8687(3) -0.05180(5) 0.0581(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
F14 0.1056(10) 0.0993(10) 0.0456(6) 0.0117(6) 0.0250(6) -0.0079(8)
F24 0.1076(10) 0.0993(10) 0.0558(7) 0.0186(6) 0.0343(6) 0.0069(8)
N11 0.0489(7) 0.0583(8) 0.0441(7) 0.0042(6) 0.0187(6) 0.0213(6)
C11 0.0391(7) 0.0502(8) 0.0397(7) 0.0008(6) 0.0097(6) 0.0063(6)
C12 0.0555(9) 0.0488(9) 0.0557(9) 0.0031(7) 0.0132(7) 0.0120(7)
C13 0.0655(11) 0.0531(10) 0.0571(10) 0.0143(8) 0.0077(8) 0.0014(8)
C14 0.0588(10) 0.0675(11) 0.0394(8) 0.0023(8) 0.0112(7) -0.0105(8)
C15 0.0584(10) 0.0600(10) 0.0442(8) -0.0076(7) 0.0162(7) 0.0034(8)
C16 0.0520(9) 0.0499(9) 0.0432(8) 0.0008(7) 0.0113(6) 0.0100(7)
N21 0.0530(8) 0.0682(9) 0.0453(7) 0.0046(6) 0.0173(6) 0.0291(7)
C21 0.0407(7) 0.0541(9) 0.0428(8) 0.0025(7) 0.0092(6) 0.0163(7)
C22 0.0579(10) 0.0551(10) 0.0591(10) -0.0057(8) 0.0053(8) 0.0022(8)
C23 0.0599(10) 0.0585(11) 0.0691(12) 0.0106(9) 0.0144(9) -0.0035(8)
C24 0.0581(10) 0.0648(11) 0.0472(9) 0.0115(8) 0.0147(7) 0.0093(8)
C25 0.0737(12) 0.0587(10) 0.0456(9) -0.0031(7) 0.0095(8) -0.0004(9)
C26 0.0598(10) 0.0517(9) 0.0506(9) 0.0034(7) 0.0119(7) -0.0010(8)
O31 0.1302(14) 0.189(2) 0.0743(10) 0.0645(11) 0.0639(10) 0.1252(15)
O34 0.0924(10) 0.1215(13) 0.0644(8) 0.0334(8) 0.0421(8) 0.0748(10)
C31 0.0714(12) 0.0911(14) 0.0502(10) 0.0185(9) 0.0300(8) 0.0476(11)
C32 0.0965(15) 0.0988(16) 0.0576(11) 0.0263(11) 0.0448(11) 0.0608(13)
C33 0.0971(15) 0.0874(14) 0.0560(11) 0.0160(10) 0.0421(11) 0.0488(13)
C34 0.0607(10) 0.0711(11) 0.0450(8) 0.0078(8) 0.0215(7) 0.0315(9)

_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
F14 C14 1.3557(18) . ?
F24 C24 1.3532(18) . ?
N11 C31 1.326(2) . ?
N11 C11 1.4177(18) . ?
C11 C16 1.387(2) . ?
C11 C12 1.387(2) . ?
C12 C13 1.375(2) . ?
C13 C14 1.374(3) . ?
C14 C15 1.365(3) . ?
C15 C16 1.383(2) . ?
N21 C34 1.321(2) . ?
N21 C21 1.4331(19) . ?
C21 C26 1.376(2) . ?
C21 C22 1.382(2) . ?
C22 C23 1.381(2) . ?
C23 C24 1.364(3) . ?
C24 C25 1.362(3) . ?
C25 C26 1.381(2) . ?
O31 C31 1.218(2) . ?
O34 C34 1.2210(19) . ?
C31 C32 1.512(2) . ?
C32 C33 1.459(3) . ?
C33 C34 1.504(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C31 N11 C11 127.88(13) . . ?
C16 C11 C12 119.65(14) . . ?
C16 C11 N11 122.61(14) . . ?
C12 C11 N11 117.60(13) . . ?
C13 C12 C11 120.24(15) . . ?
C12 C13 C14 118.87(16) . . ?
F14 C14 C15 118.71(16) . . ?
F14 C14 C13 118.96(16) . . ?
C15 C14 C13 122.33(15) . . ?
C14 C15 C16 118.74(15) . . ?
C15 C16 C11 120.17(15) . . ?
C34 N21 C21 123.88(13) . . ?
C26 C21 C22 120.03(15) . . ?
C26 C21 N21 119.65(15) . . ?
C22 C21 N21 120.28(15) . . ?
C23 C22 C21 119.82(16) . . ?
C24 C23 C22 118.77(17) . . ?
F24 C24 C25 118.74(17) . . ?
F24 C24 C23 118.65(17) . . ?
C25 C24 C23 122.61(16) . . ?
C24 C25 C26 118.51(17) . . ?
C21 C26 C25 120.25(16) . . ?
O31 C31 N11 123.20(16) . . ?
O31 C31 C32 121.44(16) . . ?
N11 C31 C32 115.35(14) . . ?
C33 C32 C31 113.05(16) . . ?
C32 C33 C34 114.46(16) . . ?
O34 C34 N21 122.53(15) . . ?
O34 C34 C33 122.39(16) . . ?
N21 C34 C33 115.07(14) . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        27.99
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.042

data_3F
_database_code_depnum_ccdc_archive 'CCDC 696970'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 F2 N2 O2'
_chemical_formula_weight         332.34

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   11.3328(8)
_cell_length_b                   9.5211(6)
_cell_length_c                   15.3985(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1661.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1814
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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 APEX 2 Bruker'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20610
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0154
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         27.00
_reflns_number_total             1814
_reflns_number_gt                1373
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0817P)²+0.3604P] 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         1814
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1483
_refine_ls_wR_factor_gt          0.1377
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
F14 F 0.20097(10) 0.05384(18) 0.69180(9) 0.0995(5) Uani 1 1 d . . .
N11 N 0.67282(12) 0.10164(13) 0.60987(9) 0.0493(4) Uani 1 1 d . . .
H11 H 0.6954 0.1868 0.6014 0.059 Uiso 1 1 calc R . .
C11 C 0.55294(14) 0.08230(16) 0.63239(10) 0.0464(4) Uani 1 1 d . . .
C12 C 0.48899(16) -0.03591(19) 0.60916(12) 0.0580(5) Uani 1 1 d . . .
H12 H 0.5257 -0.1089 0.5795 0.070 Uiso 1 1 calc R . .
C13 C 0.37045(17) -0.0452(2) 0.63012(13) 0.0684(5) Uani 1 1 d . . .
H13 H 0.3272 -0.1247 0.6153 0.082 Uiso 1 1 calc R . .
C14 C 0.31807(16) 0.0635(2) 0.67264(12) 0.0661(5) Uani 1 1 d . . .
C15 C 0.37841(16) 0.1805(2) 0.69687(12) 0.0659(5) Uani 1 1 d . . .
H15 H 0.3406 0.2530 0.7263 0.079 Uiso 1 1 calc R . .
C16 C 0.49709(15) 0.18954(17) 0.67687(12) 0.0554(4) Uani 1 1 d . . .
H16 H 0.5398 0.2685 0.6935 0.066 Uiso 1 1 calc R . .
O21 O 0.73332(12) -0.12360(11) 0.60784(12) 0.0820(6) Uani 1 1 d . . .
C21 C 0.75502(15) 0.00156(17) 0.60034(12) 0.0543(4) Uani 1 1 d . . .
C22 C 0.87789(16) 0.05395(18) 0.58054(14) 0.0645(5) Uani 1 1 d . . .
H22A H 0.8736 0.1524 0.5647 0.077 Uiso 1 1 calc . . .
H22B H 0.9256 0.0468 0.6327 0.077 Uiso 1 1 calc . . .
C23 C 0.93770(13) -0.02537(17) 0.50854(11) 0.0509(4) Uani 1 1 d . . .
H23A H 0.8916 -0.0156 0.4558 0.061 Uiso 1 1 calc . . .
H23B H 0.9400 -0.1243 0.5234 0.061 Uiso 1 1 calc . . .

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
F14 0.0434(6) 0.1693(15) 0.0859(9) -0.0120(9) 0.0099(5) 0.0047(7)
N11 0.0483(8) 0.0301(6) 0.0694(9) 0.0005(5) 0.0123(6) 0.0001(5)
C11 0.0441(8) 0.0414(8) 0.0537(8) 0.0060(6) 0.0053(6) 0.0058(6)
C12 0.0494(10) 0.0519(10) 0.0726(11) -0.0034(8) 0.0107(8) -0.0012(7)
C13 0.0520(11) 0.0815(14) 0.0717(11) 0.0007(10) 0.0049(9) -0.0114(9)
C14 0.0397(9) 0.1031(15) 0.0555(10) 0.0041(10) 0.0039(7) 0.0085(10)
C15 0.0550(11) 0.0814(13) 0.0612(10) -0.0032(9) 0.0049(8) 0.0256(10)
C16 0.0553(10) 0.0492(9) 0.0615(10) -0.0022(7) 0.0018(7) 0.0118(7)
O21 0.0540(8) 0.0310(7) 0.1611(16) 0.0018(7) 0.0304(8) 0.0012(5)
C21 0.0464(9) 0.0349(8) 0.0815(11) -0.0053(7) 0.0178(8) -0.0008(6)
C22 0.0509(10) 0.0451(9) 0.0976(14) -0.0175(9) 0.0242(9) -0.0082(7)
C23 0.0408(9) 0.0493(9) 0.0627(9) -0.0050(7) 0.0053(7) -0.0015(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
F14 C14 1.363(2) . ?
N11 C21 1.341(2) . ?
N11 C11 1.414(2) . ?
C11 C16 1.383(2) . ?
C11 C12 1.386(2) . ?
C12 C13 1.384(3) . ?
C13 C14 1.361(3) . ?
C14 C15 1.360(3) . ?
C15 C16 1.382(2) . ?
O21 C21 1.2223(19) . ?
C21 C22 1.510(2) . ?
C22 C23 1.503(2) . ?
C23 C23 1.515(3) 5_756 ?

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
C21 N11 C11 127.00(13) . . ?
C16 C11 C12 119.22(16) . . ?
C16 C11 N11 117.71(15) . . ?
C12 C11 N11 123.03(14) . . ?
C13 C12 C11 119.96(18) . . ?
C14 C13 C12 119.12(19) . . ?
C13 C14 F14 118.5(2) . . ?
C13 C14 C15 122.41(18) . . ?
F14 C14 C15 119.06(19) . . ?
C14 C15 C16 118.63(17) . . ?
C15 C16 C11 120.65(17) . . ?
O21 C21 N11 122.88(16) . . ?
O21 C21 C22 121.78(15) . . ?
N11 C21 C22 115.34(14) . . ?
C23 C22 C21 113.51(14) . . ?
C22 C23 C23 112.84(17) . 5_756 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.037

data_4F
_database_code_depnum_ccdc_archive 'CCDC 696971'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 F2 N2 O2'
_chemical_formula_weight         360.40

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   18.084(3)
_cell_length_b                   5.0326(7)
_cell_length_c                   39.311(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.792(4)
_cell_angle_gamma                90.00
_cell_volume                     3552.6(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3406
_cell_measurement_theta_min      1.04
_cell_measurement_theta_max      25.76

_exptl_crystal_description       Needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1520
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD APEX 2 Bruker'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20696
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_theta_min         1.04
_diffrn_reflns_theta_max         25.76
_reflns_number_total             3406
_reflns_number_gt                2172
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0661P)²+3.5009P] 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         3406
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1427
_refine_ls_wR_factor_gt          0.1225
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_restrained_S_all      0.978
_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
O11 O 0.54410(10) 0.1322(3) 0.56001(4) 0.0503(5) Uani 1 1 d . . .
O12 O 0.79521(12) -0.2094(3) 0.36528(5) 0.0652(6) Uani 1 1 d . . .
C11 C 0.54774(12) -0.1082(4) 0.55484(6) 0.0374(5) Uani 1 1 d . . .
C12 C 0.57784(13) -0.2203(4) 0.52361(6) 0.0413(6) Uani 1 1 d . . .
H12A H 0.6042 -0.3839 0.5300 0.050 Uiso 1 1 calc . . .
H12B H 0.5362 -0.2646 0.5067 0.050 Uiso 1 1 calc . . .
C13 C 0.62946(13) -0.0369(5) 0.50738(6) 0.0422(6) Uani 1 1 d . . .
H13A H 0.6741 -0.0098 0.5232 0.051 Uiso 1 1 calc . . .
H13B H 0.6054 0.1342 0.5033 0.051 Uiso 1 1 calc . . .
C14 C 0.65131(13) -0.1421(4) 0.47384(6) 0.0413(6) Uani 1 1 d . . .
H14A H 0.6760 -0.3121 0.4781 0.050 Uiso 1 1 calc . . .
H14B H 0.6065 -0.1724 0.4582 0.050 Uiso 1 1 calc . . .
C15 C 0.70205(14) 0.0403(5) 0.45679(6) 0.0428(6) Uani 1 1 d . . .
H15A H 0.7478 0.0650 0.4720 0.051 Uiso 1 1 calc . . .
H15B H 0.6782 0.2125 0.4534 0.051 Uiso 1 1 calc . . .
C16 C 0.72137(13) -0.0605(4) 0.42264(6) 0.0425(6) Uani 1 1 d . . .
H16A H 0.6758 -0.0813 0.4072 0.051 Uiso 1 1 calc . . .
H16B H 0.7444 -0.2340 0.4259 0.051 Uiso 1 1 calc . . .
C17 C 0.77350(13) 0.1228(4) 0.40635(6) 0.0414(6) Uani 1 1 d . . .
H17A H 0.7506 0.2969 0.4034 0.050 Uiso 1 1 calc . . .
H17B H 0.8191 0.1423 0.4218 0.050 Uiso 1 1 calc . . .
C18 C 0.79269(13) 0.0270(4) 0.37219(6) 0.0404(5) Uani 1 1 d . . .
F21 F 0.37407(11) -0.1480(4) 0.68850(4) 0.0884(6) Uani 1 1 d . . .
N21 N 0.52337(10) -0.2909(3) 0.57582(4) 0.0396(5) Uani 1 1 d . . .
H21 H 0.5311 -0.4543 0.5709 0.048 Uiso 1 1 calc R . .
C21 C 0.48627(12) -0.2453(4) 0.60523(5) 0.0369(5) Uani 1 1 d . . .
C22 C 0.50552(14) -0.0398(5) 0.62794(6) 0.0450(6) Uani 1 1 d . . .
H22 H 0.5437 0.0765 0.6242 0.054 Uiso 1 1 calc R . .
C23 C 0.46776(16) -0.0078(5) 0.65632(6) 0.0548(7) Uani 1 1 d . . .
H23 H 0.4801 0.1299 0.6717 0.066 Uiso 1 1 calc R . .
C24 C 0.41212(16) -0.1820(5) 0.66130(6) 0.0549(7) Uani 1 1 d . . .
C25 C 0.39314(15) -0.3891(5) 0.63978(6) 0.0531(7) Uani 1 1 d . . .
H25 H 0.3559 -0.5075 0.6441 0.064 Uiso 1 1 calc R . .
C26 C 0.43066(14) -0.4191(5) 0.61135(6) 0.0472(6) Uani 1 1 d . . .
H26 H 0.4182 -0.5583 0.5962 0.057 Uiso 1 1 calc R . .
F31 F 0.90781(13) 0.1365(4) 0.22411(5) 0.1078(8) Uani 1 1 d . . .
N31 N 0.80841(11) 0.2207(4) 0.35056(4) 0.0418(5) Uani 1 1 d . . .
H31 H 0.8035 0.3815 0.3573 0.050 Uiso 1 1 calc R . .
C31 C 0.83223(13) 0.1869(4) 0.31777(6) 0.0407(5) Uani 1 1 d . . .
C32 C 0.88360(16) -0.0030(6) 0.31171(7) 0.0578(7) Uani 1 1 d . . .
H32 H 0.9016 -0.1201 0.3290 0.069 Uiso 1 1 calc R . .
C33 C 0.90863(18) -0.0203(6) 0.27986(7) 0.0696(9) Uani 1 1 d . . .
H33 H 0.9433 -0.1488 0.2756 0.084 Uiso 1 1 calc R . .
C34 C 0.88207(18) 0.1518(6) 0.25516(7) 0.0652(8) Uani 1 1 d . . .
C35 C 0.83068(19) 0.3425(6) 0.26012(7) 0.0708(9) Uani 1 1 d . . .
H35 H 0.8129 0.4580 0.2426 0.085 Uiso 1 1 calc R . .
C36 C 0.80588(16) 0.3588(5) 0.29206(6) 0.0575(7) Uani 1 1 d . . .
H36 H 0.7711 0.4875 0.2961 0.069 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O11 0.0722(12) 0.0294(9) 0.0539(10) -0.0044(7) 0.0264(9) 0.0000(8)
O12 0.1101(16) 0.0292(9) 0.0653(12) -0.0043(8) 0.0475(11) -0.0037(10)
C11 0.0392(13) 0.0326(12) 0.0414(12) -0.0005(10) 0.0088(10) 0.0007(10)
C12 0.0507(14) 0.0333(12) 0.0423(12) -0.0064(10) 0.0148(11) -0.0016(10)
C13 0.0475(14) 0.0386(13) 0.0428(12) -0.0066(10) 0.0148(11) -0.0056(11)
C14 0.0496(14) 0.0377(12) 0.0389(12) -0.0041(10) 0.0140(10) -0.0052(11)
C15 0.0523(14) 0.0359(12) 0.0426(12) -0.0033(10) 0.0154(11) -0.0047(11)
C16 0.0531(15) 0.0360(12) 0.0408(12) -0.0033(10) 0.0155(11) -0.0050(11)
C17 0.0509(14) 0.0350(12) 0.0404(12) -0.0018(10) 0.0144(11) -0.0023(11)
C18 0.0491(14) 0.0315(12) 0.0431(12) -0.0038(10) 0.0158(11) -0.0017(10)
F21 0.1227(16) 0.0852(13) 0.0694(11) -0.0054(10) 0.0616(11) 0.0081(12)
N21 0.0539(12) 0.0267(9) 0.0417(10) -0.0027(8) 0.0196(9) -0.0001(8)
C21 0.0430(13) 0.0319(11) 0.0371(12) 0.0011(9) 0.0104(10) 0.0044(10)
C22 0.0548(15) 0.0392(13) 0.0421(13) -0.0042(10) 0.0102(11) -0.0036(11)
C23 0.0773(19) 0.0468(15) 0.0418(13) -0.0084(12) 0.0141(13) 0.0088(14)
C24 0.0716(18) 0.0542(16) 0.0441(14) 0.0022(12) 0.0289(13) 0.0129(14)
C25 0.0595(16) 0.0481(15) 0.0562(15) 0.0071(13) 0.0254(13) -0.0022(13)
C26 0.0578(16) 0.0390(13) 0.0471(13) -0.0017(11) 0.0164(12) -0.0051(12)
F31 0.175(2) 0.0955(15) 0.0668(11) -0.0036(10) 0.0742(13) 0.0006(14)
N31 0.0589(13) 0.0289(9) 0.0411(11) -0.0033(8) 0.0203(9) -0.0015(9)
C31 0.0488(14) 0.0338(12) 0.0417(12) 0.0003(10) 0.0148(11) -0.0061(10)
C32 0.0690(18) 0.0548(16) 0.0542(15) 0.0083(13) 0.0262(13) 0.0125(14)
C33 0.089(2) 0.0548(17) 0.0741(19) -0.0006(16) 0.0490(17) 0.0088(16)
C34 0.095(2) 0.0591(17) 0.0491(16) -0.0066(14) 0.0409(15) -0.0126(17)
C35 0.103(2) 0.0659(19) 0.0468(16) 0.0136(14) 0.0218(16) 0.0029(18)
C36 0.0743(19) 0.0484(15) 0.0535(15) 0.0050(13) 0.0231(13) 0.0079(14)

_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
O11 C11 1.230(3) . ?
O12 C18 1.222(3) . ?
C11 N21 1.344(3) . ?
C11 C12 1.510(3) . ?
C12 C13 1.507(3) . ?
C13 C14 1.516(3) . ?
C14 C15 1.510(3) . ?
C15 C16 1.514(3) . ?
C16 C17 1.514(3) . ?
C17 C18 1.505(3) . ?
C18 N31 1.346(3) . ?
F21 C24 1.349(3) . ?
N21 C21 1.422(3) . ?
C21 C26 1.375(3) . ?
C21 C22 1.384(3) . ?
C22 C23 1.384(3) . ?
C23 C24 1.366(4) . ?
C24 C25 1.361(4) . ?
C25 C26 1.383(3) . ?
F31 C34 1.359(3) . ?
N31 C31 1.417(3) . ?
C31 C36 1.372(3) . ?
C31 C32 1.373(3) . ?
C32 C33 1.384(3) . ?
C33 C34 1.346(4) . ?
C34 C35 1.366(4) . ?
C35 C36 1.385(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
O11 C11 N21 122.9(2) . . ?
O11 C11 C12 122.3(2) . . ?
N21 C11 C12 114.78(19) . . ?
C13 C12 C11 114.60(19) . . ?
C12 C13 C14 113.12(19) . . ?
C15 C14 C13 114.10(19) . . ?
C14 C15 C16 113.95(19) . . ?
C15 C16 C17 113.04(19) . . ?
C18 C17 C16 113.76(19) . . ?
O12 C18 N31 123.2(2) . . ?
O12 C18 C17 121.9(2) . . ?
N31 C18 C17 114.82(19) . . ?
C11 N21 C21 127.50(18) . . ?
C26 C21 C22 119.7(2) . . ?
C26 C21 N21 117.7(2) . . ?
C22 C21 N21 122.6(2) . . ?
C23 C22 C21 119.8(2) . . ?
C24 C23 C22 118.9(2) . . ?
F21 C24 C25 118.4(3) . . ?
F21 C24 C23 119.1(2) . . ?
C25 C24 C23 122.6(2) . . ?
C24 C25 C26 118.3(2) . . ?
C21 C26 C25 120.7(2) . . ?
C18 N31 C31 126.69(19) . . ?
C36 C31 C32 119.6(2) . . ?
C36 C31 N31 118.5(2) . . ?
C32 C31 N31 121.7(2) . . ?
C31 C32 C33 120.1(3) . . ?
C34 C33 C32 119.0(3) . . ?
C33 C34 F31 118.7(3) . . ?
C33 C34 C35 122.7(2) . . ?
F31 C34 C35 118.6(3) . . ?
C34 C35 C36 118.0(3) . . ?
C31 C36 C35 120.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.76
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.042

data_5F
_database_code_depnum_ccdc_archive 'CCDC 696972'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H26 F2 N2 O2'
_chemical_formula_weight         388.45

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   18.1488(12)
_cell_length_b                   5.0327(3)
_cell_length_c                   43.840(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.817(2)
_cell_angle_gamma                90.00
_cell_volume                     3945.6(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4263
_cell_measurement_theta_min      0.94
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1648
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD APEX 2 BRUKER'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25190
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_theta_min         0.94
_diffrn_reflns_theta_max         27.00
_reflns_number_total             4263
_reflns_number_gt                2902
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0972P)²+1.8062P] 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         4263
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0520
_refine_ls_wR_factor_ref         0.1700
_refine_ls_wR_factor_gt          0.1500
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
N1 N 0.50168(9) 0.3314(3) 0.09218(4) 0.0404(4) Uani 1 1 d . . .
H1 H 0.5079 0.4951 0.0876 0.048 Uiso 1 1 calc R . .
N2 N 0.82054(9) -0.2578(3) -0.15892(4) 0.0419(4) Uani 1 1 d . . .
H2 H 0.8165 -0.4186 -0.1528 0.050 Uiso 1 1 calc R . .
O1 O 0.52192(8) -0.0919(3) 0.07800(3) 0.0504(4) Uani 1 1 d . . .
O2 O 0.80903(11) 0.1724(3) -0.14573(4) 0.0664(5) Uani 1 1 d . . .
C1 C 0.52433(10) 0.1479(3) 0.07346(4) 0.0363(4) Uani 1 1 d . . .
C2 C 0.54963(11) 0.2623(4) 0.04500(5) 0.0425(5) Uani 1 1 d . . .
H2A H 0.5058 0.3092 0.0301 0.051 Uiso 1 1 calc . . .
H2B H 0.5773 0.4246 0.0508 0.051 Uiso 1 1 calc . . .
C3 C 0.59789(11) 0.0788(4) 0.02962(5) 0.0419(5) Uani 1 1 d . . .
H3A H 0.5725 -0.0904 0.0256 0.050 Uiso 1 1 calc . . .
H3B H 0.6443 0.0468 0.0437 0.050 Uiso 1 1 calc . . .
C4 C 0.61574(11) 0.1877(4) -0.00061(4) 0.0408(5) Uani 1 1 d . . .
H4A H 0.5692 0.2219 -0.0146 0.049 Uiso 1 1 calc . . .
H4B H 0.6416 0.3561 0.0035 0.049 Uiso 1 1 calc . . .
C5 C 0.66343(11) 0.0043(4) -0.01655(5) 0.0426(5) Uani 1 1 d . . .
H5A H 0.7106 -0.0254 -0.0028 0.051 Uiso 1 1 calc . . .
H5B H 0.6383 -0.1659 -0.0200 0.051 Uiso 1 1 calc . . .
C6 C 0.67946(11) 0.1077(4) -0.04717(4) 0.0418(5) Uani 1 1 d . . .
H6A H 0.7045 0.2781 -0.0437 0.050 Uiso 1 1 calc . . .
H6B H 0.6324 0.1365 -0.0610 0.050 Uiso 1 1 calc . . .
C7 C 0.72750(12) -0.0770(4) -0.06285(5) 0.0439(5) Uani 1 1 d . . .
H7A H 0.7030 -0.2486 -0.0659 0.053 Uiso 1 1 calc . . .
H7B H 0.7750 -0.1028 -0.0492 0.053 Uiso 1 1 calc . . .
C8 C 0.74232(12) 0.0238(4) -0.09393(4) 0.0425(5) Uani 1 1 d . . .
H8A H 0.6951 0.0437 -0.1079 0.051 Uiso 1 1 calc . . .
H8B H 0.7656 0.1976 -0.0911 0.051 Uiso 1 1 calc . . .
C9 C 0.79252(11) -0.1613(4) -0.10853(4) 0.0414(5) Uani 1 1 d . . .
H9A H 0.8398 -0.1809 -0.0946 0.050 Uiso 1 1 calc . . .
H9B H 0.7693 -0.3352 -0.1112 0.050 Uiso 1 1 calc . . .
C10 C 0.80747(11) -0.0639(4) -0.13940(4) 0.0402(5) Uani 1 1 d . . .
C11 C 0.46852(11) 0.2830(4) 0.11883(4) 0.0377(4) Uani 1 1 d . . .
F11 F 0.36690(11) 0.1839(3) 0.19438(4) 0.0919(6) Uani 1 1 d . . .
C12 C 0.41346(12) 0.4574(4) 0.12454(5) 0.0466(5) Uani 1 1 d . . .
H12 H 0.3992 0.5971 0.1109 0.056 Uiso 1 1 calc R . .
C13 C 0.37948(13) 0.4263(5) 0.15024(5) 0.0555(6) Uani 1 1 d . . .
H13 H 0.3426 0.5436 0.1541 0.067 Uiso 1 1 calc R . .
C14 C 0.40138(14) 0.2198(5) 0.16974(5) 0.0552(6) Uani 1 1 d . . .
C15 C 0.45654(14) 0.0458(5) 0.16511(5) 0.0565(6) Uani 1 1 d . . .
H15 H 0.4708 -0.0920 0.1790 0.068 Uiso 1 1 calc R . .
C16 C 0.49073(12) 0.0789(4) 0.13935(5) 0.0465(5) Uani 1 1 d . . .
H16 H 0.5285 -0.0364 0.1359 0.056 Uiso 1 1 calc R . .
F21 F 0.90466(13) -0.1728(4) -0.27342(4) 0.1101(7) Uani 1 1 d . . .
C21 C 0.84042(11) -0.2237(4) -0.18873(5) 0.0412(5) Uani 1 1 d . . .
C22 C 0.89079(14) -0.0335(5) -0.19419(6) 0.0594(6) Uani 1 1 d . . .
H22 H 0.9107 0.0835 -0.1785 0.071 Uiso 1 1 calc R . .
C23 C 0.91193(16) -0.0159(5) -0.22304(6) 0.0712(8) Uani 1 1 d . . .
H23 H 0.9457 0.1135 -0.2269 0.085 Uiso 1 1 calc R . .
C24 C 0.88274(17) -0.1893(5) -0.24544(6) 0.0673(7) Uani 1 1 d . . .
C25 C 0.83179(17) -0.3785(6) -0.24096(6) 0.0736(8) Uani 1 1 d . . .
H25 H 0.8118 -0.4931 -0.2569 0.088 Uiso 1 1 calc R . .
C26 C 0.81055(15) -0.3955(5) -0.21210(5) 0.0589(6) Uani 1 1 d . . .
H26 H 0.7760 -0.5233 -0.2085 0.071 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0564(10) 0.0275(7) 0.0418(9) 0.0025(7) 0.0211(8) 0.0006(7)
N2 0.0606(10) 0.0279(8) 0.0415(9) 0.0032(7) 0.0207(8) 0.0014(7)
O1 0.0746(10) 0.0274(7) 0.0555(9) 0.0021(6) 0.0294(8) 0.0009(6)
O2 0.1186(15) 0.0292(7) 0.0641(10) 0.0056(7) 0.0514(10) 0.0048(8)
C1 0.0398(10) 0.0300(9) 0.0411(11) 0.0014(8) 0.0132(8) 0.0013(7)
C2 0.0544(12) 0.0332(9) 0.0433(11) 0.0040(8) 0.0180(9) 0.0037(8)
C3 0.0490(11) 0.0389(10) 0.0412(11) 0.0056(8) 0.0173(9) 0.0070(8)
C4 0.0476(11) 0.0385(10) 0.0388(10) 0.0043(8) 0.0150(9) 0.0038(8)
C5 0.0526(11) 0.0379(10) 0.0412(11) 0.0060(8) 0.0187(9) 0.0057(8)
C6 0.0512(11) 0.0393(10) 0.0382(10) 0.0071(8) 0.0172(9) 0.0062(9)
C7 0.0568(12) 0.0381(10) 0.0402(11) 0.0034(8) 0.0183(9) 0.0042(9)
C8 0.0577(12) 0.0345(10) 0.0392(11) 0.0047(8) 0.0196(9) 0.0076(8)
C9 0.0524(11) 0.0337(9) 0.0410(11) 0.0041(8) 0.0157(9) 0.0059(8)
C10 0.0509(11) 0.0309(9) 0.0429(11) 0.0015(8) 0.0197(9) 0.0021(8)
C11 0.0462(10) 0.0328(9) 0.0362(10) -0.0025(8) 0.0131(8) -0.0042(8)
F11 0.1350(15) 0.0884(11) 0.0695(10) 0.0044(9) 0.0666(10) -0.0109(10)
C12 0.0581(12) 0.0400(10) 0.0452(12) 0.0015(9) 0.0183(10) 0.0046(9)
C13 0.0639(14) 0.0504(13) 0.0589(14) -0.0072(11) 0.0296(11) -0.0003(11)
C14 0.0747(15) 0.0540(13) 0.0436(12) -0.0039(10) 0.0291(11) -0.0146(11)
C15 0.0810(16) 0.0472(12) 0.0424(12) 0.0088(10) 0.0136(11) -0.0072(12)
C16 0.0559(12) 0.0409(11) 0.0443(12) 0.0041(9) 0.0135(10) 0.0022(9)
F21 0.187(2) 0.0950(13) 0.0681(11) 0.0048(9) 0.0783(13) 0.0019(13)
C21 0.0529(12) 0.0342(10) 0.0404(11) 0.0014(8) 0.0187(9) 0.0056(8)
C22 0.0762(15) 0.0522(13) 0.0565(14) -0.0068(11) 0.0307(12) -0.0119(11)
C23 0.0955(19) 0.0559(14) 0.0754(18) 0.0028(13) 0.0525(16) -0.0083(13)
C24 0.105(2) 0.0597(15) 0.0467(13) 0.0084(12) 0.0391(14) 0.0136(14)
C25 0.108(2) 0.0683(17) 0.0491(14) -0.0132(12) 0.0279(14) -0.0046(15)
C26 0.0785(16) 0.0512(13) 0.0521(14) -0.0077(11) 0.0252(12) -0.0100(12)

_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
N1 C1 1.345(2) . ?
N1 C11 1.424(2) . ?
N2 C10 1.346(2) . ?
N2 C21 1.424(2) . ?
O1 C1 1.225(2) . ?
O2 C10 1.223(2) . ?
C1 C2 1.515(2) . ?
C2 C3 1.509(3) . ?
C3 C4 1.519(3) . ?
C4 C5 1.516(3) . ?
C5 C6 1.513(3) . ?
C6 C7 1.517(3) . ?
C7 C8 1.520(3) . ?
C8 C9 1.519(3) . ?
C9 C10 1.507(2) . ?
C11 C16 1.380(3) . ?
C11 C12 1.384(3) . ?
F11 C14 1.350(2) . ?
C12 C13 1.382(3) . ?
C13 C14 1.362(3) . ?
C14 C15 1.371(3) . ?
C15 C16 1.389(3) . ?
F21 C24 1.355(3) . ?
C21 C22 1.372(3) . ?
C21 C26 1.379(3) . ?
C22 C23 1.386(3) . ?
C23 C24 1.353(4) . ?
C24 C25 1.364(4) . ?
C25 C26 1.387(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C11 126.79(15) . . ?
C10 N2 C21 126.59(16) . . ?
O1 C1 N1 123.66(17) . . ?
O1 C1 C2 122.16(16) . . ?
N1 C1 C2 114.10(15) . . ?
C3 C2 C1 114.58(16) . . ?
C2 C3 C4 113.28(16) . . ?
C5 C4 C3 113.96(16) . . ?
C6 C5 C4 114.27(16) . . ?
C5 C6 C7 113.78(16) . . ?
C6 C7 C8 113.86(16) . . ?
C9 C8 C7 112.54(16) . . ?
C10 C9 C8 113.05(15) . . ?
O2 C10 N2 123.18(18) . . ?
O2 C10 C9 122.36(17) . . ?
N2 C10 C9 114.44(16) . . ?
C16 C11 C12 119.60(18) . . ?
C16 C11 N1 123.02(17) . . ?
C12 C11 N1 117.33(17) . . ?
C13 C12 C11 120.8(2) . . ?
C14 C13 C12 118.4(2) . . ?
F11 C14 C13 118.6(2) . . ?
F11 C14 C15 118.9(2) . . ?
C13 C14 C15 122.49(19) . . ?
C14 C15 C16 118.9(2) . . ?
C11 C16 C15 119.9(2) . . ?
C22 C21 C26 119.8(2) . . ?
C22 C21 N2 121.64(19) . . ?
C26 C21 N2 118.50(18) . . ?
C21 C22 C23 120.0(2) . . ?
C24 C23 C22 119.1(2) . . ?
C23 C24 F21 118.6(2) . . ?
C23 C24 C25 122.5(2) . . ?
F21 C24 C25 118.9(3) . . ?
C24 C25 C26 118.4(2) . . ?
C21 C26 C25 120.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.061

data_2IBr
_database_code_depnum_ccdc_archive 'CCDC 696973'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 Br I N2 O2'
_chemical_formula_weight         473.10

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   17.459(5)
_cell_length_b                   4.8268(13)
_cell_length_c                   9.851(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.666(9)
_cell_angle_gamma                90.00
_cell_volume                     818.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1298
_cell_measurement_theta_min      1.18
_cell_measurement_theta_max      24.14

_exptl_crystal_description       Needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.920
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_absorpt_coefficient_mu    4.406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.510
_exptl_absorpt_correction_T_max  0.640
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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 APEX 2 Bruker'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7958
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.18
_diffrn_reflns_theta_max         24.14
_reflns_number_total             1298
_reflns_number_gt                887
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0837P)²+0.8888P] 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         1298
_refine_ls_number_parameters     109
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1494
_refine_ls_wR_factor_gt          0.1118
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_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
I1 I 0.5698(3) 1.2029(11) 0.3537(6) 0.0622(11) Uani 0.50 1 d PD . .
Br1 Br 0.5789(5) 1.1343(19) 0.3544(9) 0.0642(16) Uani 0.50 1 d PD . .
N11 N 0.8631(3) 0.8513(10) 0.7780(6) 0.0438(14) Uani 1 1 d . . .
H11 H 0.8703 0.6775 0.7947 0.053 Uiso 1 1 calc R . .
C11 C 0.7980(4) 0.9260(12) 0.6786(7) 0.0376(15) Uani 1 1 d . . .
C12 C 0.7284(5) 0.7911(16) 0.6778(9) 0.058(2) Uani 1 1 d . . .
H12 H 0.7248 0.6540 0.7427 0.070 Uiso 1 1 calc R . .
C13 C 0.6640(4) 0.8568(14) 0.5818(8) 0.0528(19) Uani 1 1 d . . .
H13 H 0.6178 0.7600 0.5805 0.063 Uiso 1 1 calc R . .
C14 C 0.6679(3) 1.0623(14) 0.4894(5) 0.0434(16) Uani 1 1 d D . .
C15 C 0.7369(4) 1.1973(16) 0.4894(8) 0.0535(19) Uani 1 1 d . . .
H15 H 0.7397 1.3372 0.4255 0.064 Uiso 1 1 calc R . .
C16 C 0.8023(4) 1.1292(14) 0.5825(8) 0.0487(18) Uani 1 1 d . . .
H16 H 0.8490 1.2203 0.5804 0.058 Uiso 1 1 calc R . .
O21 O 0.9125(3) 1.2790(8) 0.8267(6) 0.0535(14) Uani 1 1 d . . .
C21 C 0.9150(4) 1.0290(13) 0.8491(7) 0.0416(16) Uani 1 1 d . . .
C22 C 0.9737(4) 0.8988(14) 0.9585(8) 0.0491(18) Uani 1 1 d . . .
H22A H 0.9466 0.7937 1.0197 0.059 Uiso 1 1 calc . . .
H22B H 1.0048 0.7697 0.9154 0.059 Uiso 1 1 calc . . .

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 0.0531(13) 0.054(3) 0.0720(12) 0.0072(13) -0.0117(9) 0.0166(11)
Br1 0.060(2) 0.054(4) 0.0698(18) -0.0005(19) -0.0177(13) 0.0256(15)
N11 0.053(3) 0.020(3) 0.052(4) 0.002(2) -0.008(3) 0.003(2)
C11 0.046(4) 0.019(3) 0.043(4) -0.002(3) -0.004(3) 0.001(3)
C12 0.059(5) 0.044(4) 0.068(6) 0.013(4) 0.001(4) -0.007(4)
C13 0.053(4) 0.051(5) 0.051(5) 0.002(4) -0.004(4) -0.008(3)
C14 0.044(4) 0.039(3) 0.043(4) -0.003(3) -0.004(3) 0.007(3)
C15 0.061(5) 0.057(5) 0.039(4) 0.008(4) -0.005(3) 0.000(4)
C16 0.046(4) 0.050(4) 0.047(4) 0.013(3) -0.002(3) -0.007(3)
O21 0.072(3) 0.016(2) 0.063(4) 0.002(2) -0.016(3) 0.005(2)
C21 0.047(4) 0.033(4) 0.043(4) 0.001(3) 0.002(3) 0.005(3)
C22 0.056(4) 0.027(3) 0.055(5) -0.001(3) -0.015(3) 0.003(3)

_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 C14 2.1002(11) . ?
Br1 C14 1.8999(11) . ?
N11 C21 1.355(8) . ?
N11 C11 1.417(8) . ?
C11 C12 1.377(10) . ?
C11 C16 1.374(9) . ?
C12 C13 1.379(11) . ?
C13 C14 1.355(9) . ?
C14 C15 1.370(10) . ?
C15 C16 1.379(10) . ?
O21 C21 1.226(8) . ?
C21 C22 1.494(10) . ?
C22 C22 1.489(14) 3_777 ?

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
C21 N11 C11 125.9(5) . . ?
C12 C11 C16 118.9(6) . . ?
C12 C11 N11 119.2(6) . . ?
C16 C11 N11 121.8(6) . . ?
C11 C12 C13 120.8(7) . . ?
C14 C13 C12 120.1(6) . . ?
C13 C14 C15 119.4(5) . . ?
C13 C14 Br1 118.5(6) . . ?
C15 C14 Br1 121.9(6) . . ?
C13 C14 I1 122.5(5) . . ?
C15 C14 I1 118.0(5) . . ?
Br1 C14 I1 8.8(4) . . ?
C16 C15 C14 121.1(7) . . ?
C11 C16 C15 119.6(7) . . ?
O21 C21 N11 121.9(6) . . ?
O21 C21 C22 122.9(6) . . ?
N11 C21 C22 115.1(6) . . ?
C22 C22 C21 113.9(7) 3_777 . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        24.14
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.892
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.174

data_3IBr
_database_code_depnum_ccdc_archive 'CCDC 696974'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 Br I N2 O2'
_chemical_formula_weight         501.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   18.9243(9)
_cell_length_b                   4.8077(2)
_cell_length_c                   10.1235(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.5350(10)
_cell_angle_gamma                90.00
_cell_volume                     919.31(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1981
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.810
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    3.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.546
_exptl_absorpt_correction_T_max  0.676
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD APEX 2 BRUKER'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11569
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         27.00
_reflns_number_total             1981
_reflns_number_gt                1757
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0619P)²+0.1670P] 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         1981
_refine_ls_number_parameters     118
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0894
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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
I1 I 0.06626(11) 0.3092(6) 0.3336(3) 0.0535(2) Uani 0.50 1 d PD . .
Br1 Br 0.0704(2) 0.3288(12) 0.3552(5) 0.0665(8) Uani 0.50 1 d PD . .
C11 C 0.27034(13) 0.5862(5) 0.6265(2) 0.0411(5) Uani 1 1 d . . .
C12 C 0.20613(17) 0.7191(6) 0.6361(3) 0.0542(7) Uani 1 1 d . . .
H12 H 0.2017 0.8583 0.6989 0.065 Uiso 1 1 calc R . .
C13 C 0.14802(16) 0.6463(6) 0.5525(3) 0.0567(7) Uani 1 1 d . . .
H13 H 0.1052 0.7383 0.5593 0.068 Uiso 1 1 calc R . .
C14 C 0.15340(10) 0.4378(5) 0.4593(2) 0.0470(5) Uani 1 1 d D . .
C15 C 0.21846(16) 0.3085(6) 0.4492(3) 0.0542(7) Uani 1 1 d . . .
H15 H 0.2230 0.1696 0.3864 0.065 Uiso 1 1 calc R . .
C16 C 0.27660(14) 0.3831(6) 0.5311(3) 0.0510(6) Uani 1 1 d . . .
H16 H 0.3200 0.2965 0.5221 0.061 Uiso 1 1 calc R . .
N21 N 0.32837(13) 0.6656(4) 0.7131(3) 0.0481(5) Uani 1 1 d . . .
H21 H 0.3351 0.8407 0.7261 0.058 Uiso 1 1 calc R . .
O21 O 0.37313(13) 0.2392(4) 0.7576(2) 0.0604(6) Uani 1 1 d . . .
C21 C 0.37387(13) 0.4888(5) 0.7769(2) 0.0419(5) Uani 1 1 d . . .
C22 C 0.42571(18) 0.6246(6) 0.8761(3) 0.0591(8) Uani 1 1 d . . .
H22A H 0.4539 0.7568 0.8297 0.071 Uiso 1 1 calc . . .
H22B H 0.3992 0.7286 0.9386 0.071 Uiso 1 1 calc . . .
C23 C 0.47434(15) 0.4314(5) 0.9515(3) 0.0518(6) Uani 1 1 d . . .
H23A H 0.5007 0.3264 0.8891 0.062 Uiso 1 1 calc . . .
H23B H 0.4462 0.3001 0.9986 0.062 Uiso 1 1 calc . . .

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 0.0372(4) 0.0702(5) 0.0499(8) -0.0076(5) -0.0229(3) -0.0077(3)
Br1 0.0446(6) 0.0932(12) 0.0579(16) -0.0115(8) -0.0289(6) -0.0105(5)
C11 0.0404(12) 0.0382(10) 0.0433(12) 0.0022(9) -0.0091(10) -0.0032(9)
C12 0.0494(16) 0.0552(14) 0.0560(17) -0.0132(12) -0.0121(13) 0.0082(12)
C13 0.0399(14) 0.0663(16) 0.0624(18) -0.0073(13) -0.0095(13) 0.0071(12)
C14 0.0381(12) 0.0559(13) 0.0458(13) 0.0052(11) -0.0085(10) -0.0054(10)
C15 0.0461(16) 0.0649(17) 0.0498(16) -0.0138(12) -0.0107(13) 0.0011(11)
C16 0.0384(13) 0.0613(14) 0.0521(15) -0.0115(12) -0.0076(11) 0.0041(11)
N21 0.0506(13) 0.0350(9) 0.0561(13) -0.0041(8) -0.0177(11) -0.0016(8)
O21 0.0698(14) 0.0362(8) 0.0709(14) -0.0019(9) -0.0308(11) -0.0037(9)
C21 0.0432(12) 0.0357(10) 0.0454(12) 0.0006(9) -0.0094(10) -0.0034(9)
C22 0.0653(19) 0.0406(11) 0.0673(18) -0.0033(12) -0.0301(15) -0.0050(12)
C23 0.0500(15) 0.0455(12) 0.0570(15) -0.0019(11) -0.0197(12) -0.0049(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
I1 C14 2.1125(19) . ?
Br1 C14 1.910(2) . ?
C11 C12 1.382(4) . ?
C11 C16 1.383(4) . ?
C11 N21 1.415(3) . ?
C12 C13 1.390(4) . ?
C13 C14 1.385(4) . ?
C14 C15 1.389(4) . ?
C15 C16 1.384(4) . ?
N21 C21 1.346(3) . ?
O21 C21 1.216(3) . ?
C21 C22 1.509(4) . ?
C22 C23 1.485(4) . ?
C23 C23 1.492(5) 3_667 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C11 C16 119.3(2) . . ?
C12 C11 N21 118.9(2) . . ?
C16 C11 N21 121.8(2) . . ?
C11 C12 C13 120.5(3) . . ?
C14 C13 C12 120.6(3) . . ?
C13 C14 C15 118.5(2) . . ?
C13 C14 Br1 118.8(3) . . ?
C15 C14 Br1 122.6(3) . . ?
C13 C14 I1 122.3(2) . . ?
C15 C14 I1 119.2(2) . . ?
Br1 C14 I1 4.0(3) . . ?
C16 C15 C14 121.0(2) . . ?
C15 C16 C11 120.1(2) . . ?
C21 N21 C11 125.2(2) . . ?
O21 C21 N21 123.1(2) . . ?
O21 C21 C22 122.3(2) . . ?
N21 C21 C22 114.6(2) . . ?
C23 C22 C21 115.4(2) . . ?
C22 C23 C23 114.8(3) . 3_667 ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.698
_refine_diff_density_rms         0.118

data_3BrCl
_database_code_depnum_ccdc_archive 'CCDC 696975'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 Br Cl N2 O2'
_chemical_formula_weight         409.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   9.7510(6)
_cell_length_b                   11.2001(7)
_cell_length_c                   9.6534(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 119.494(2)
_cell_angle_gamma                90.00
_cell_volume                     917.64(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1983
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_absorpt_coefficient_mu    2.398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.716
_exptl_absorpt_correction_T_max  0.788
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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 APEX 2 Bruker'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11949
_diffrn_reflns_av_R_equivalents  0.1333
_diffrn_reflns_av_sigmaI/netI    0.0692
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         27.00
_reflns_number_total             1983
_reflns_number_gt                1197
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0812P)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         1983
_refine_ls_number_parameters     118
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1341
_refine_ls_wR_factor_gt          0.1263
_refine_ls_goodness_of_fit_ref   0.892
_refine_ls_restrained_S_all      0.905
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.5387(3) 0.2119(2) 0.8118(2) 0.0917(5) Uani 0.50 1 d PD . .
Cl1 Cl 0.5317(7) 0.2051(5) 0.7513(5) 0.0928(13) Uani 0.50 1 d PD . .
N11 N 0.0625(3) -0.18440(18) 0.4804(2) 0.0509(5) Uani 1 1 d . . .
H11 H 0.0347 -0.1934 0.3816 0.061 Uiso 1 1 calc R . .
C11 C 0.1724(3) -0.0920(2) 0.5602(3) 0.0507(6) Uani 1 1 d . . .
C12 C 0.2338(3) -0.0344(3) 0.4774(3) 0.0704(8) Uani 1 1 d . . .
H12 H 0.2019 -0.0566 0.3730 0.085 Uiso 1 1 calc R . .
C13 C 0.3426(4) 0.0563(3) 0.5477(4) 0.0843(9) Uani 1 1 d . . .
H13 H 0.3836 0.0948 0.4908 0.101 Uiso 1 1 calc R . .
C14 C 0.3899(3) 0.0895(2) 0.7014(4) 0.0771(8) Uani 1 1 d D . .
C15 C 0.3278(4) 0.0324(3) 0.7841(4) 0.0823(9) Uani 1 1 d . . .
H15 H 0.3596 0.0550 0.8883 0.099 Uiso 1 1 calc R . .
C16 C 0.2201(3) -0.0569(3) 0.7154(3) 0.0661(7) Uani 1 1 d . . .
H16 H 0.1786 -0.0945 0.7725 0.079 Uiso 1 1 calc R . .
O21 O 0.0215(3) -0.25693(19) 0.6747(2) 0.0793(6) Uani 1 1 d . . .
C21 C -0.0043(3) -0.2598(2) 0.5372(3) 0.0527(6) Uani 1 1 d . . .
C22 C -0.1145(3) -0.3501(2) 0.4212(3) 0.0607(7) Uani 1 1 d . . .
H22A H -0.1069 -0.3472 0.3247 0.073 Uiso 1 1 calc . . .
H22B H -0.2218 -0.3300 0.3933 0.073 Uiso 1 1 calc . . .
C23 C -0.0779(3) -0.4763(2) 0.4885(3) 0.0572(6) Uani 1 1 d . . .
H23A H -0.1619 -0.5292 0.4171 0.069 Uiso 1 1 calc . . .
H23B H -0.0754 -0.4771 0.5902 0.069 Uiso 1 1 calc . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0583(6) 0.0702(7) 0.1132(14) -0.0274(8) 0.0166(9) -0.0185(4)
Cl1 0.0556(11) 0.0724(15) 0.105(3) -0.033(2) 0.005(2) -0.0192(9)
N11 0.0732(13) 0.0447(12) 0.0404(9) 0.0002(8) 0.0322(9) 0.0014(10)
C11 0.0577(13) 0.0420(14) 0.0519(12) 0.0039(10) 0.0266(11) 0.0073(11)
C12 0.0799(18) 0.068(2) 0.0661(15) 0.0064(14) 0.0378(14) -0.0049(15)
C13 0.0746(18) 0.072(2) 0.107(2) 0.0145(19) 0.0458(17) -0.0093(17)
C14 0.0564(15) 0.0523(18) 0.102(2) -0.0079(16) 0.0229(15) -0.0042(13)
C15 0.0774(19) 0.073(2) 0.0795(18) -0.0258(17) 0.0251(15) -0.0037(17)
C16 0.0774(16) 0.0620(18) 0.0639(15) -0.0141(14) 0.0387(13) -0.0054(14)
O21 0.1335(18) 0.0679(13) 0.0564(11) -0.0018(9) 0.0620(12) -0.0132(13)
C21 0.0735(15) 0.0425(13) 0.0494(13) 0.0059(11) 0.0360(12) 0.0095(12)
C22 0.0720(16) 0.0498(17) 0.0604(14) 0.0007(11) 0.0327(12) -0.0008(12)
C23 0.0693(15) 0.0457(15) 0.0679(14) 0.0008(12) 0.0424(12) -0.0083(12)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Cl1 0.559(5) . ?
Br1 C14 1.897(3) . ?
Cl1 C14 1.779(4) . ?
N11 C21 1.338(3) . ?
N11 C11 1.414(3) . ?
C11 C12 1.374(3) . ?
C11 C16 1.389(3) . ?
C12 C13 1.381(4) . ?
C13 C14 1.371(4) . ?
C14 C15 1.375(4) . ?
C15 C16 1.363(4) . ?
O21 C21 1.224(2) . ?
C21 C22 1.499(4) . ?
C22 C23 1.523(4) . ?
C23 C23 1.518(5) 3_546 ?

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
Cl1 Br1 C14 69.4(6) . . ?
Br1 Cl1 C14 93.6(7) . . ?
C21 N11 C11 129.06(19) . . ?
C12 C11 C16 118.9(2) . . ?
C12 C11 N11 117.2(2) . . ?
C16 C11 N11 123.8(2) . . ?
C11 C12 C13 120.6(3) . . ?
C14 C13 C12 120.0(3) . . ?
C13 C14 C15 119.5(2) . . ?
C13 C14 Cl1 107.1(3) . . ?
C15 C14 Cl1 133.4(3) . . ?
C13 C14 Br1 124.1(3) . . ?
C15 C14 Br1 116.4(3) . . ?
Cl1 C14 Br1 17.09(17) . . ?
C16 C15 C14 120.8(3) . . ?
C15 C16 C11 120.1(3) . . ?
O21 C21 N11 123.1(2) . . ?
O21 C21 C22 121.2(2) . . ?
N11 C21 C22 115.74(19) . . ?
C21 C22 C23 112.1(2) . . ?
C22 C23 C23 113.2(2) . 3_546 ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.070

data_4BrCl
_database_code_depnum_ccdc_archive 'CCDC 696976'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 Br Cl N2 O2'
_chemical_formula_weight         437.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   22.022(4)
_cell_length_b                   5.1048(10)
_cell_length_c                   17.836(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.024(5)
_cell_angle_gamma                90.00
_cell_volume                     1927.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2095
_cell_measurement_theta_min      1.92
_cell_measurement_theta_max      27.00

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    2.289
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.669
_exptl_absorpt_correction_T_max  0.777
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD APEX 2 Bruker'
_diffrn_measurement_method       hemisphere
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12245
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         27.00
_reflns_number_total             2095
_reflns_number_gt                1492
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0499P)²+0.6068P] 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         2095
_refine_ls_number_parameters     127
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0890
_refine_ls_wR_factor_gt          0.0818
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.05628(14) 0.8427(9) 0.2068(2) 0.0719(4) Uani 0.50 1 d PD . .
Cl1 Cl 0.0649(4) 0.845(2) 0.2069(6) 0.0856(18) Uani 0.50 1 d PD . .
O1 O 0.31949(7) 1.1505(2) 0.09341(10) 0.0555(4) Uani 1 1 d . . .
N1 N 0.29619(7) 0.7239(3) 0.10571(9) 0.0407(4) Uani 1 1 d . . .
H1 H 0.3081 0.5664 0.1001 0.049 Uiso 1 1 calc R . .
C1 C 0.33459(9) 0.9200(3) 0.09504(11) 0.0389(4) Uani 1 1 d . . .
C2 C 0.39802(9) 0.8322(3) 0.08784(12) 0.0442(5) Uani 1 1 d . . .
H2A H 0.3944 0.6541 0.0681 0.053 Uiso 1 1 calc . . .
H2B H 0.4279 0.8313 0.1392 0.053 Uiso 1 1 calc . . .
C3 C 0.42345(9) 1.0043(3) 0.03449(11) 0.0428(4) Uani 1 1 d . . .
H3A H 0.3931 1.0082 -0.0166 0.051 Uiso 1 1 calc . . .
H3B H 0.4280 1.1816 0.0548 0.051 Uiso 1 1 calc . . .
C4 C 0.48652(10) 0.9124(4) 0.02595(12) 0.0452(5) Uani 1 1 d . . .
H4A H 0.4817 0.7366 0.0045 0.054 Uiso 1 1 calc . . .
H4B H 0.5165 0.9039 0.0773 0.054 Uiso 1 1 calc . . .
C11 C 0.23880(9) 0.7531(3) 0.12508(10) 0.0347(4) Uani 1 1 d . . .
C12 C 0.19680(9) 0.9557(3) 0.09656(11) 0.0420(4) Uani 1 1 d . . .
H12 H 0.2051 1.0756 0.0614 0.050 Uiso 1 1 calc R . .
C13 C 0.14268(9) 0.9785(4) 0.12065(12) 0.0477(5) Uani 1 1 d . . .
H13 H 0.1146 1.1152 0.1022 0.057 Uiso 1 1 calc R . .
C14 C 0.13014(9) 0.7996(4) 0.17186(11) 0.0450(5) Uani 1 1 d D . .
C15 C 0.16988(10) 0.5928(4) 0.19831(11) 0.0456(5) Uani 1 1 d . . .
H15 H 0.1603 0.4691 0.2316 0.055 Uiso 1 1 calc R . .
C16 C 0.22418(9) 0.5704(4) 0.17501(11) 0.0414(4) Uani 1 1 d . . .
H16 H 0.2515 0.4310 0.1930 0.050 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0451(7) 0.1015(9) 0.0833(8) -0.0097(6) 0.0414(6) 0.0012(7)
Cl1 0.048(2) 0.121(3) 0.107(3) 0.0002(19) 0.0520(19) 0.0050(17)
O1 0.0526(9) 0.0301(6) 0.0969(11) 0.0019(6) 0.0423(8) 0.0037(6)
N1 0.0419(10) 0.0289(7) 0.0585(9) -0.0002(7) 0.0258(8) 0.0034(7)
C1 0.0407(11) 0.0353(9) 0.0473(10) 0.0020(8) 0.0234(8) 0.0023(8)
C2 0.0393(11) 0.0404(10) 0.0592(12) 0.0064(8) 0.0243(9) 0.0060(8)
C3 0.0376(10) 0.0387(10) 0.0584(11) 0.0034(8) 0.0237(9) 0.0024(8)
C4 0.0384(11) 0.0412(9) 0.0629(12) 0.0039(9) 0.0258(9) 0.0036(8)
C11 0.0336(10) 0.0318(8) 0.0417(9) -0.0038(7) 0.0157(8) -0.0014(7)
C12 0.0390(11) 0.0376(9) 0.0519(11) 0.0043(8) 0.0169(9) -0.0004(8)
C13 0.0375(12) 0.0443(10) 0.0633(12) 0.0005(9) 0.0172(10) 0.0055(9)
C14 0.0348(11) 0.0552(12) 0.0498(11) -0.0114(9) 0.0200(9) -0.0052(9)
C15 0.0469(12) 0.0500(11) 0.0442(10) 0.0030(8) 0.0196(9) -0.0064(9)
C16 0.0432(11) 0.0365(9) 0.0465(10) 0.0029(8) 0.0159(9) 0.0013(8)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C14 1.908(3) . ?
Cl1 C14 1.733(5) . ?
O1 C1 1.221(2) . ?
N1 C1 1.358(2) . ?
N1 C11 1.407(2) . ?
C1 C2 1.506(3) . ?
C2 C3 1.512(2) . ?
C3 C4 1.513(3) . ?
C4 C4 1.521(4) 5_675 ?
C11 C16 1.387(2) . ?
C11 C12 1.387(3) . ?
C12 C13 1.379(3) . ?
C13 C14 1.373(3) . ?
C14 C15 1.369(3) . ?
C15 C16 1.375(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C11 126.36(14) . . ?
O1 C1 N1 122.54(18) . . ?
O1 C1 C2 122.56(16) . . ?
N1 C1 C2 114.88(15) . . ?
C1 C2 C3 113.21(15) . . ?
C4 C3 C2 113.14(16) . . ?
C3 C4 C4 113.7(2) . 5_675 ?
C16 C11 C12 119.16(17) . . ?
C16 C11 N1 118.01(16) . . ?
C12 C11 N1 122.82(15) . . ?
C13 C12 C11 119.65(17) . . ?
C14 C13 C12 120.07(18) . . ?
C15 C14 C13 121.03(17) . . ?
C15 C14 Cl1 119.5(5) . . ?
C13 C14 Cl1 119.4(5) . . ?
C15 C14 Br1 119.9(2) . . ?
C13 C14 Br1 119.1(2) . . ?
Cl1 C14 Br1 2.3(4) . . ?
C14 C15 C16 119.11(17) . . ?
C15 C16 C11 120.90(18) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.054
##ENd


