# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences.
# This journal is © The Royal Society of Chemistry and Owner Societies 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_collect_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H15 Cl2 N O'
_chemical_formula_weight         284.17

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)/m

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

_cell_length_a                   4.7973(5)
_cell_length_b                   8.5668(8)
_cell_length_c                   17.3529(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.321(2)
_cell_angle_gamma                90.00
_cell_volume                     713.15(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1537
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      24.28

_exptl_crystal_description       Plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.443
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8291
_exptl_absorpt_correction_T_max  0.9825
_exptl_absorpt_process_details   '(SADABS 2007/4 Bruker)'

_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  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4185
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.17
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1348
_reflns_number_gt                1090
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 v2.2-0 (Bruker, 2007)'
_computing_cell_refinement       'SAINT+  V7.46A (Bruker, 2007)'
_computing_data_reduction        'SAINT+  V7.46A (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSHELL v4.02 (Bruker, 2000)'
_computing_publication_material  'XCIF v6.12 (Bruker, 2001)'

_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)+(0.0472P)²+0.2208P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1348
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1076
_refine_ls_wR_factor_gt          0.0988
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
Cl1 Cl 0.9027(2) 0.7500 1.01905(5) 0.0900(4) Uani 1 2 d S . .
Cl2 Cl 0.91117(17) 0.7500 0.42239(4) 0.0683(3) Uani 1 2 d S . .
N1 N -0.6757(5) 0.7500 0.55495(14) 0.0631(7) Uani 1 2 d S . .
H1A H -0.8056 0.7500 0.5206 0.076 Uiso 1 2 calc SR . .
C1 C -0.5783(5) 0.6166(3) 0.58069(13) 0.0709(6) Uani 1 1 d . . .
H1 H -0.6508 0.5233 0.5618 0.085 Uiso 1 1 calc R . .
C2 C -0.3737(5) 0.6136(3) 0.63444(14) 0.0769(7) Uani 1 1 d . . .
H2 H -0.3060 0.5182 0.6520 0.092 Uiso 1 1 calc R . .
C3 C -0.2637(6) 0.7500 0.66368(18) 0.0732(10) Uani 1 2 d S . .
C4 C -0.0525(9) 0.6922(5) 0.7221(3) 0.0520(10) Uani 0.50 1 d P . .
C5 C 0.0792(9) 0.6999(4) 0.7620(3) 0.0511(11) Uani 0.50 1 d P . .
C6 C 0.2868(6) 0.7500 0.82349(17) 0.0739(10) Uani 1 2 d S . .
C7 C 0.3877(5) 0.6118(3) 0.85358(13) 0.0744(7) Uani 1 1 d . . .
H7 H 0.3245 0.5175 0.8335 0.089 Uiso 1 1 calc R . .
C8 C 0.5792(5) 0.6107(3) 0.91254(12) 0.0668(6) Uani 1 1 d . . .
H8 H 0.6457 0.5168 0.9323 0.080 Uiso 1 1 calc R . .
C9 C 0.6709(6) 0.7500 0.94194(16) 0.0575(7) Uani 1 2 d S . .
C1S C 0.1990(10) 0.7500 0.2214(3) 0.1036(14) Uani 1 2 d S . .
H1S1 H 0.2601 0.8555 0.2136 0.155 Uiso 0.50 1 calc PR . .
H1S2 H 0.2189 0.6921 0.1744 0.155 Uiso 0.50 1 calc PR . .
H1S3 H 0.3102 0.7024 0.2611 0.155 Uiso 0.50 1 calc PR . .
H1E H 0.007(5) 0.591(3) 0.7411(14) 0.078(7) Uiso 1 1 d . . .
O1S O -0.0726(8) 0.7500 0.2429(2) 0.1548(17) Uani 1 2 d S . .
H1S H -0.0831 0.7319 0.2892 0.232 Uiso 0.50 1 calc PR . .

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 0.0809(6) 0.1209(8) 0.0681(6) 0.000 -0.0223(4) 0.000
Cl2 0.0694(5) 0.0711(5) 0.0643(5) 0.000 -0.0089(4) 0.000
N1 0.0473(13) 0.092(2) 0.0502(14) 0.000 0.0023(10) 0.000
C1 0.0808(16) 0.0638(14) 0.0682(14) -0.0141(11) 0.0197(12) -0.0111(12)
C2 0.0786(16) 0.0817(17) 0.0705(15) 0.0199(13) 0.0171(13) 0.0293(13)
C3 0.0437(16) 0.128(3) 0.0482(17) 0.000 0.0076(13) 0.000
C4 0.048(2) 0.052(3) 0.056(2) 0.0035(17) 0.0019(19) 0.0013(16)
C5 0.045(2) 0.055(3) 0.054(2) 0.0011(16) 0.0037(18) -0.0051(15)
C6 0.0424(16) 0.133(3) 0.0464(16) 0.000 0.0059(13) 0.000
C7 0.0599(13) 0.1006(19) 0.0629(13) -0.0179(13) 0.0069(11) -0.0141(13)
C8 0.0661(13) 0.0724(15) 0.0620(13) 0.0018(11) 0.0051(10) 0.0022(11)
C9 0.0487(15) 0.077(2) 0.0463(15) 0.000 0.0022(12) 0.000
C1S 0.131(4) 0.082(3) 0.098(3) 0.000 0.023(3) 0.000
O1S 0.130(3) 0.248(5) 0.086(2) 0.000 -0.008(2) 0.000

_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 C9 1.735(3) . ?
N1 C1 1.312(3) . ?
N1 C1 1.312(3) 4_575 ?
C1 C2 1.351(3) . ?
C2 C3 1.377(3) . ?
C3 C2 1.377(3) 4_575 ?
C3 C4 1.513(5) 4_575 ?
C3 C4 1.513(5) . ?
C4 C5 0.937(5) . ?
C4 C4 0.990(8) 4_575 ?
C4 C5 1.314(5) 4_575 ?
C5 C5 0.858(8) 4_575 ?
C5 C4 1.314(5) 4_575 ?
C5 C6 1.517(5) . ?
C6 C7 1.381(3) 4_575 ?
C6 C7 1.381(3) . ?
C6 C5 1.517(5) 4_575 ?
C7 C8 1.371(3) . ?
C8 C9 1.370(3) . ?
C9 C8 1.370(3) 4_575 ?
C1S O1S 1.357(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C1 121.2(3) . 4_575 ?
N1 C1 C2 120.5(2) . . ?
C1 C2 C3 120.9(2) . . ?
C2 C3 C2 116.0(3) . 4_575 ?
C2 C3 C4 141.1(2) . 4_575 ?
C2 C3 C4 102.9(2) 4_575 4_575 ?
C2 C3 C4 102.9(2) . . ?
C2 C3 C4 141.1(2) 4_575 . ?
C4 C3 C4 38.2(3) 4_575 . ?
C5 C4 C4 86.0(4) . 4_575 ?
C5 C4 C5 40.6(4) . 4_575 ?
C4 C4 C5 45.3(2) 4_575 4_575 ?
C5 C4 C3 156.7(5) . . ?
C4 C4 C3 70.90(17) 4_575 . ?
C5 C4 C3 116.2(3) 4_575 . ?
C5 C5 C4 94.0(4) 4_575 . ?
C5 C5 C4 45.3(2) 4_575 4_575 ?
C4 C5 C4 48.7(5) . 4_575 ?
C5 C5 C6 73.56(15) 4_575 . ?
C4 C5 C6 167.6(5) . . ?
C4 C5 C6 118.9(3) 4_575 . ?
C7 C6 C7 118.1(3) 4_575 . ?
C7 C6 C5 104.5(2) 4_575 4_575 ?
C7 C6 C5 137.4(2) . 4_575 ?
C7 C6 C5 137.4(2) 4_575 . ?
C7 C6 C5 104.5(2) . . ?
C5 C6 C5 32.9(3) 4_575 . ?
C8 C7 C6 121.4(2) . . ?
C9 C8 C7 119.0(2) . . ?
C8 C9 C8 121.3(3) 4_575 . ?
C8 C9 Cl1 119.36(14) 4_575 . ?
C8 C9 Cl1 119.36(14) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.033
_database_code_depnum_ccdc_archive 'CCDC 1008122'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_collect_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H15 Br Cl N O'
_chemical_formula_weight         328.63

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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/m

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

_cell_length_a                   4.8200(5)
_cell_length_b                   8.7182(9)
_cell_length_c                   17.3278(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.278(2)
_cell_angle_gamma                90.00
_cell_volume                     728.14(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1376
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      23.77

_exptl_crystal_description       Bar
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_absorpt_coefficient_mu    2.994
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5597
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   '(SADABS 2007/4 Bruker)'

_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  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4602
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         26.99
_reflns_number_total             1689
_reflns_number_gt                1270
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 v2.2-0 (Bruker, 2007)'
_computing_cell_refinement       'SAINT+  V7.46A (Bruker, 2007)'
_computing_data_reduction        'SAINT+  V7.46A (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSHELL v4.02 (Bruker, 2000)'
_computing_publication_material  'XCIF v6.12 (Bruker, 2001)'

_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)+(0.0360P)²+0.4017P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1689
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0928
_refine_ls_wR_factor_gt          0.0841
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.002
_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 0.89945(9) 0.7500 1.02599(3) 0.0761(2) Uani 1 2 d S . .
N1 N -0.6901(7) 0.7500 0.55218(19) 0.0615(9) Uani 1 2 d S . .
H1A H -0.8194 0.7500 0.5178 0.074 Uiso 1 2 calc SR . .
C1 C -0.5925(7) 0.6186(4) 0.57816(18) 0.0701(8) Uani 1 1 d . . .
H1 H -0.6646 0.5269 0.5593 0.084 Uiso 1 1 calc R . .
C2 C -0.3888(7) 0.6156(4) 0.63192(19) 0.0809(10) Uani 1 1 d . . .
H2 H -0.3210 0.5218 0.6493 0.097 Uiso 1 1 calc R . .
C3 C -0.2798(8) 0.7500 0.6615(2) 0.0811(16) Uani 1 2 d S . .
C4 C -0.0678(12) 0.6903(7) 0.7201(3) 0.0523(13) Uani 0.50 1 d P . .
C5 C 0.0643(11) 0.7023(6) 0.7594(3) 0.0500(14) Uani 0.50 1 d P . .
C6 C 0.2719(8) 0.7500 0.8209(2) 0.0722(13) Uani 1 2 d S . .
C7 C 0.3722(6) 0.6138(4) 0.85096(17) 0.0718(9) Uani 1 1 d . . .
H7 H 0.3094 0.5213 0.8307 0.086 Uiso 1 1 calc R . .
C8 C 0.5637(6) 0.6125(4) 0.91048(16) 0.0632(7) Uani 1 1 d . . .
H8 H 0.6300 0.5202 0.9302 0.076 Uiso 1 1 calc R . .
C9 C 0.6546(7) 0.7500 0.9400(2) 0.0524(9) Uani 1 2 d S . .
C1S C 0.2417(14) 0.7500 0.2253(4) 0.1045(18) Uani 1 2 d S . .
H1S1 H 0.3045 0.8537 0.2190 0.157 Uiso 0.50 1 calc PR . .
H1S2 H 0.2697 0.6944 0.1782 0.157 Uiso 0.50 1 calc PR . .
H1S3 H 0.3447 0.7019 0.2662 0.157 Uiso 0.50 1 calc PR . .
Cl1 Cl 0.8961(2) 0.7500 0.42034(6) 0.0712(3) Uani 1 2 d S . .
H1E H -0.008(6) 0.596(4) 0.7401(18) 0.071(9) Uiso 1 1 d . . .
O1S O -0.0276(13) 0.7500 0.2427(3) 0.199(3) Uani 1 2 d S . .
H1S H -0.0460 0.7405 0.2895 0.299 Uiso 0.50 1 calc PR . .

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 0.0696(3) 0.0917(4) 0.0669(3) 0.000 -0.0181(2) 0.000
N1 0.0497(18) 0.086(3) 0.0490(18) 0.000 0.0007(14) 0.000
C1 0.076(2) 0.0643(19) 0.0703(19) -0.0132(16) 0.0148(16) -0.0070(16)
C2 0.076(2) 0.095(3) 0.072(2) 0.0228(19) 0.0153(18) 0.030(2)
C3 0.043(2) 0.154(5) 0.047(2) 0.000 0.0063(18) 0.000
C4 0.048(3) 0.053(3) 0.056(3) 0.004(2) 0.001(3) 0.000(2)
C5 0.047(3) 0.046(4) 0.057(3) 0.000(2) 0.004(2) -0.003(2)
C6 0.039(2) 0.129(4) 0.049(2) 0.000 0.0047(17) 0.000
C7 0.0582(17) 0.097(2) 0.0604(17) -0.0187(17) 0.0045(14) -0.0140(17)
C8 0.0630(16) 0.0648(18) 0.0619(17) -0.0013(14) 0.0045(14) 0.0021(14)
C9 0.0437(19) 0.065(2) 0.048(2) 0.000 0.0022(15) 0.000
C1S 0.127(5) 0.090(4) 0.097(4) 0.000 0.021(4) 0.000
Cl1 0.0712(7) 0.0785(7) 0.0637(6) 0.000 -0.0109(5) 0.000
O1S 0.138(4) 0.372(11) 0.088(3) 0.000 -0.004(3) 0.000

_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 C9 1.897(4) . ?
N1 C1 1.317(4) 4_575 ?
N1 C1 1.317(4) . ?
C1 C2 1.350(5) . ?
C2 C3 1.382(4) . ?
C3 C2 1.382(4) 4_575 ?
C3 C4 1.528(7) . ?
C3 C4 1.528(7) 4_575 ?
C4 C5 0.937(7) . ?
C4 C4 1.041(12) 4_575 ?
C4 C5 1.320(7) 4_575 ?
C5 C5 0.831(10) 4_575 ?
C5 C4 1.320(6) 4_575 ?
C5 C6 1.516(7) . ?
C6 C7 1.382(4) . ?
C6 C7 1.382(4) 4_575 ?
C6 C5 1.516(7) 4_575 ?
C7 C8 1.381(4) . ?
C8 C9 1.374(3) . ?
C9 C8 1.374(3) 4_575 ?
C1S O1S 1.334(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C1 120.9(4) 4_575 . ?
N1 C1 C2 120.7(3) . . ?
C1 C2 C3 120.9(3) . . ?
C2 C3 C2 116.0(4) . 4_575 ?
C2 C3 C4 102.1(3) . . ?
C2 C3 C4 141.9(3) 4_575 . ?
C2 C3 C4 141.9(3) . 4_575 ?
C2 C3 C4 102.1(3) 4_575 4_575 ?
C4 C3 C4 39.8(5) . 4_575 ?
C5 C4 C4 83.6(5) . 4_575 ?
C5 C4 C5 38.7(5) . 4_575 ?
C4 C4 C5 44.8(3) 4_575 4_575 ?
C5 C4 C3 153.6(7) . . ?
C4 C4 C3 70.1(2) 4_575 . ?
C5 C4 C3 114.9(5) 4_575 . ?
C5 C5 C4 96.4(5) 4_575 . ?
C5 C5 C4 44.8(3) 4_575 4_575 ?
C4 C5 C4 51.6(7) . 4_575 ?
C5 C5 C6 74.1(2) 4_575 . ?
C4 C5 C6 170.5(7) . . ?
C4 C5 C6 118.9(4) 4_575 . ?
C7 C6 C7 118.3(4) . 4_575 ?
C7 C6 C5 136.7(3) . 4_575 ?
C7 C6 C5 104.9(3) 4_575 4_575 ?
C7 C6 C5 104.9(3) . . ?
C7 C6 C5 136.7(3) 4_575 . ?
C5 C6 C5 31.8(4) 4_575 . ?
C8 C7 C6 121.3(3) . . ?
C9 C8 C7 118.8(3) . . ?
C8 C9 C8 121.5(4) 4_575 . ?
C8 C9 Br1 119.23(18) 4_575 . ?
C8 C9 Br1 119.23(18) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.048
_database_code_depnum_ccdc_archive 'CCDC 1008123'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_collect_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 Cl I N'
_chemical_formula_weight         343.58

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.6445(5)
_cell_length_b                   12.0822(6)
_cell_length_c                   13.2869(7)
_cell_angle_alpha                103.2550(10)
_cell_angle_beta                 107.3030(10)
_cell_angle_gamma                97.0320(10)
_cell_volume                     1262.22(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6773
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      30.49

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    2.720
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4764
_exptl_absorpt_correction_T_max  0.8538
_exptl_absorpt_process_details   '(SADABS 2007/4 Bruker)'

_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  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12960
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         28.00
_reflns_number_total             6059
_reflns_number_gt                5290
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 v2.2-0 (Bruker, 2007)'
_computing_cell_refinement       'SAINT+  V7.46A (Bruker, 2007)'
_computing_data_reduction        'SAINT+  V7.46A (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSHELL v4.02 (Bruker, 2000)'
_computing_publication_material  'XCIF v6.12 (Bruker, 2001)'

_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)+(0.0318P)²+0.6834P] 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         6059
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_ref         0.0681
_refine_ls_wR_factor_gt          0.0654
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.002
_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 0.43061(2) 1.274940(15) 0.298453(15) 0.04528(6) Uani 1 1 d . . .
I2 I 0.50586(2) 1.212814(17) 0.781711(16) 0.05118(7) Uani 1 1 d . . .
Cl1 Cl 0.31049(10) 0.62620(7) 0.34303(6) 0.05461(18) Uani 1 1 d . . .
Cl2 Cl 0.65314(11) 0.41939(7) 0.18438(7) 0.0615(2) Uani 1 1 d . . .
N1 N -0.1874(3) 0.5474(2) 0.5557(2) 0.0458(5) Uani 1 1 d . . .
H1A H -0.2411 0.4938 0.5725 0.055 Uiso 1 1 calc R . .
N2 N -0.1923(3) 0.5595(2) 1.0706(2) 0.0514(6) Uani 1 1 d . . .
H2A H -0.2503 0.5171 1.0956 0.062 Uiso 1 1 calc R . .
C1 C -0.2661(4) 0.5867(3) 0.4729(3) 0.0491(6) Uani 1 1 d . . .
H1 H -0.3775 0.5555 0.4332 0.059 Uiso 1 1 calc R . .
C2 C -0.1819(4) 0.6739(3) 0.4463(2) 0.0490(7) Uani 1 1 d . . .
H2 H -0.2368 0.7017 0.3887 0.059 Uiso 1 1 calc R . .
C3 C -0.0157(4) 0.7203(2) 0.5049(2) 0.0438(6) Uani 1 1 d . . .
C4 C 0.0602(4) 0.6744(3) 0.5894(2) 0.0496(7) Uani 1 1 d . . .
H4 H 0.1720 0.7026 0.6299 0.059 Uiso 1 1 calc R . .
C5 C -0.0265(4) 0.5893(3) 0.6135(2) 0.0491(7) Uani 1 1 d . . .
H5 H 0.0258 0.5598 0.6704 0.059 Uiso 1 1 calc R . .
C6 C 0.0857(4) 0.8146(3) 0.4842(3) 0.0516(7) Uani 1 1 d . . .
H6 H 0.1982 0.8343 0.5247 0.062 Uiso 1 1 calc R . .
C7 C 0.0311(4) 0.8724(2) 0.4141(2) 0.0473(6) Uani 1 1 d . . .
H7 H -0.0814 0.8519 0.3737 0.057 Uiso 1 1 calc R . .
C8 C 0.1293(4) 0.9668(2) 0.3926(2) 0.0432(6) Uani 1 1 d . . .
C9 C 0.0607(3) 0.9999(3) 0.2984(2) 0.0488(7) Uani 1 1 d . . .
H9 H -0.0453 0.9622 0.2513 0.059 Uiso 1 1 calc R . .
C10 C 0.1456(3) 1.0872(3) 0.2731(2) 0.0459(6) Uani 1 1 d . . .
H10 H 0.0977 1.1068 0.2088 0.055 Uiso 1 1 calc R . .
C11 C 0.3021(3) 1.1461(2) 0.3431(2) 0.0371(5) Uani 1 1 d . . .
C12 C 0.3735(4) 1.1180(2) 0.4395(2) 0.0465(6) Uani 1 1 d . . .
H12 H 0.4776 1.1585 0.4877 0.056 Uiso 1 1 calc R . .
C13 C 0.2866(4) 1.0279(3) 0.4632(2) 0.0496(7) Uani 1 1 d . . .
H13 H 0.3345 1.0080 0.5274 0.059 Uiso 1 1 calc R . .
C21 C -0.2260(4) 0.5365(3) 0.9624(3) 0.0547(7) Uani 1 1 d . . .
H21 H -0.3122 0.4757 0.9151 0.066 Uiso 1 1 calc R . .
C22 C -0.1339(4) 0.6023(2) 0.9207(2) 0.0486(6) Uani 1 1 d . . .
H3A H -0.1544 0.5838 0.8454 0.058 Uiso 1 1 calc R . .
C23 C -0.0094(3) 0.6968(2) 0.9911(2) 0.0383(5) Uani 1 1 d . . .
C24 C 0.0213(3) 0.7176(2) 1.1040(2) 0.0438(6) Uani 1 1 d . . .
H24 H 0.1039 0.7794 1.1535 0.053 Uiso 1 1 calc R . .
C25 C -0.0707(4) 0.6469(3) 1.1413(2) 0.0497(7) Uani 1 1 d . . .
H25 H -0.0484 0.6596 1.2165 0.060 Uiso 1 1 calc R . .
C26 C 0.0841(3) 0.7691(2) 0.9451(2) 0.0433(6) Uani 1 1 d . . .
H26 H 0.0894 0.7354 0.8762 0.052 Uiso 1 1 calc R . .
C27 C 0.1616(3) 0.8790(2) 0.9947(2) 0.0400(5) Uani 1 1 d . . .
H27 H 0.1613 0.9108 1.0653 0.048 Uiso 1 1 calc R . .
C28 C 0.2478(3) 0.9545(2) 0.9472(2) 0.0366(5) Uani 1 1 d . . .
C29 C 0.3030(3) 0.9103(2) 0.8604(2) 0.0429(6) Uani 1 1 d . . .
H29 H 0.2903 0.8304 0.8331 0.051 Uiso 1 1 calc R . .
C30 C 0.3765(3) 0.9845(2) 0.8147(2) 0.0437(6) Uani 1 1 d . . .
H30 H 0.4108 0.9542 0.7559 0.052 Uiso 1 1 calc R . .
C31 C 0.3991(3) 1.1037(2) 0.8562(2) 0.0389(5) Uani 1 1 d . . .
C32 C 0.3523(3) 1.1495(2) 0.9448(2) 0.0456(6) Uani 1 1 d . . .
H32 H 0.3715 1.2296 0.9743 0.055 Uiso 1 1 calc R . .
C33 C 0.2763(3) 1.0753(2) 0.9901(2) 0.0442(6) Uani 1 1 d . . .
H33 H 0.2440 1.1062 1.0496 0.053 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 0.04837(11) 0.03927(10) 0.04957(11) 0.01386(8) 0.01978(8) 0.00309(7)
I2 0.04377(11) 0.05250(12) 0.05377(12) 0.02777(9) 0.00711(8) -0.00393(8)
Cl1 0.0569(4) 0.0524(4) 0.0532(4) 0.0224(3) 0.0160(3) -0.0017(3)
Cl2 0.0624(5) 0.0623(5) 0.0675(5) 0.0318(4) 0.0273(4) 0.0007(4)
N1 0.0533(14) 0.0416(12) 0.0537(14) 0.0191(11) 0.0296(12) 0.0098(10)
N2 0.0523(14) 0.0455(13) 0.0697(17) 0.0298(12) 0.0296(13) 0.0090(11)
C1 0.0396(14) 0.0506(16) 0.0539(16) 0.0134(13) 0.0137(13) 0.0053(12)
C2 0.0572(17) 0.0491(16) 0.0463(15) 0.0222(13) 0.0169(13) 0.0163(13)
C3 0.0501(16) 0.0381(13) 0.0478(15) 0.0110(11) 0.0243(13) 0.0081(11)
C4 0.0439(15) 0.0507(16) 0.0508(16) 0.0118(13) 0.0142(13) 0.0067(13)
C5 0.0554(17) 0.0513(16) 0.0449(15) 0.0176(13) 0.0179(13) 0.0158(14)
C6 0.0427(15) 0.0541(17) 0.0577(18) 0.0183(14) 0.0158(13) 0.0068(13)
C7 0.0470(15) 0.0454(15) 0.0493(16) 0.0114(12) 0.0190(13) 0.0054(12)
C8 0.0484(15) 0.0367(13) 0.0475(15) 0.0093(11) 0.0240(12) 0.0051(11)
C9 0.0375(14) 0.0528(16) 0.0502(16) 0.0143(13) 0.0111(12) -0.0026(12)
C10 0.0401(14) 0.0543(16) 0.0409(14) 0.0181(12) 0.0086(11) 0.0042(12)
C11 0.0377(13) 0.0344(12) 0.0396(13) 0.0089(10) 0.0158(11) 0.0054(10)
C12 0.0427(14) 0.0442(14) 0.0447(15) 0.0144(12) 0.0052(12) 0.0010(12)
C13 0.0557(17) 0.0498(16) 0.0445(15) 0.0214(13) 0.0122(13) 0.0115(13)
C21 0.0533(17) 0.0387(14) 0.0646(19) 0.0160(14) 0.0133(15) -0.0045(13)
C22 0.0557(17) 0.0418(14) 0.0456(15) 0.0145(12) 0.0147(13) 0.0021(12)
C23 0.0394(13) 0.0354(12) 0.0414(13) 0.0145(11) 0.0131(11) 0.0061(10)
C24 0.0421(14) 0.0447(14) 0.0439(14) 0.0161(12) 0.0128(12) 0.0036(11)
C25 0.0556(17) 0.0534(16) 0.0473(16) 0.0228(13) 0.0216(14) 0.0102(14)
C26 0.0467(15) 0.0451(14) 0.0412(14) 0.0159(12) 0.0179(12) 0.0056(12)
C27 0.0401(13) 0.0446(14) 0.0367(13) 0.0159(11) 0.0128(11) 0.0064(11)
C28 0.0323(12) 0.0384(12) 0.0363(12) 0.0152(10) 0.0059(10) 0.0022(10)
C29 0.0442(14) 0.0355(13) 0.0507(15) 0.0136(11) 0.0182(12) 0.0061(11)
C30 0.0460(15) 0.0424(14) 0.0478(15) 0.0171(12) 0.0204(12) 0.0076(11)
C31 0.0295(12) 0.0410(13) 0.0434(13) 0.0192(11) 0.0056(10) 0.0001(10)
C32 0.0452(15) 0.0364(13) 0.0463(15) 0.0109(11) 0.0068(12) -0.0007(11)
C33 0.0471(15) 0.0427(14) 0.0368(13) 0.0079(11) 0.0110(11) 0.0015(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 C11 2.097(2) . ?
I2 C31 2.102(2) . ?
N1 C1 1.331(4) . ?
N1 C5 1.340(4) . ?
N2 C21 1.333(4) . ?
N2 C25 1.337(4) . ?
C1 C2 1.380(4) . ?
C2 C3 1.387(4) . ?
C3 C4 1.392(4) . ?
C3 C6 1.478(4) . ?
C4 C5 1.350(4) . ?
C6 C7 1.302(4) . ?
C7 C8 1.470(4) . ?
C8 C9 1.387(4) . ?
C8 C13 1.397(4) . ?
C9 C10 1.372(4) . ?
C10 C11 1.384(4) . ?
C11 C12 1.385(4) . ?
C12 C13 1.394(4) . ?
C21 C22 1.372(4) . ?
C22 C23 1.396(4) . ?
C23 C24 1.399(4) . ?
C23 C26 1.467(4) . ?
C24 C25 1.369(4) . ?
C26 C27 1.328(4) . ?
C27 C28 1.471(3) . ?
C28 C29 1.396(4) . ?
C28 C33 1.401(4) . ?
C29 C30 1.384(4) . ?
C30 C31 1.386(4) . ?
C31 C32 1.376(4) . ?
C32 C33 1.391(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 C5 121.6(2) . . ?
C21 N2 C25 121.8(3) . . ?
N1 C1 C2 119.7(3) . . ?
C1 C2 C3 120.3(3) . . ?
C2 C3 C4 117.2(3) . . ?
C2 C3 C6 124.8(3) . . ?
C4 C3 C6 118.0(3) . . ?
C5 C4 C3 120.8(3) . . ?
N1 C5 C4 120.3(3) . . ?
C7 C6 C3 125.6(3) . . ?
C6 C7 C8 126.6(3) . . ?
C9 C8 C13 117.7(2) . . ?
C9 C8 C7 118.5(3) . . ?
C13 C8 C7 123.8(3) . . ?
C10 C9 C8 121.5(3) . . ?
C9 C10 C11 120.2(3) . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 I1 118.89(19) . . ?
C12 C11 I1 120.94(19) . . ?
C11 C12 C13 118.9(3) . . ?
C12 C13 C8 121.5(3) . . ?
N2 C21 C22 120.1(3) . . ?
C21 C22 C23 120.1(3) . . ?
C22 C23 C24 117.6(2) . . ?
C22 C23 C26 119.6(2) . . ?
C24 C23 C26 122.8(2) . . ?
C25 C24 C23 119.8(3) . . ?
N2 C25 C24 120.4(3) . . ?
C27 C26 C23 124.8(3) . . ?
C26 C27 C28 125.5(2) . . ?
C29 C28 C33 118.3(2) . . ?
C29 C28 C27 122.4(2) . . ?
C33 C28 C27 119.2(2) . . ?
C30 C29 C28 120.5(2) . . ?
C29 C30 C31 120.1(3) . . ?
C32 C31 C30 120.4(2) . . ?
C32 C31 I2 120.74(19) . . ?
C30 C31 I2 118.8(2) . . ?
C31 C32 C33 119.6(3) . . ?
C32 C33 C28 120.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.606
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.107
_database_code_depnum_ccdc_archive 'CCDC 1008124'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_p21c

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 Cl I N'
_chemical_formula_weight         343.58

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'
Cl Cl 0.1484 0.1585 '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                   14.0901(6)
_cell_length_b                   8.0051(3)
_cell_length_c                   12.3594(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.5370(10)
_cell_angle_gamma                90.00
_cell_volume                     1329.26(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7620
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      30.10

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    2.583
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6207
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   '(SADABS 2007/4 Bruker)'

_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  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13892
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0146
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         28.99
_reflns_number_total             3525
_reflns_number_gt                3064
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 v2.2-0 (Bruker, 2007)'
_computing_cell_refinement       'SAINT+  V7.46A (Bruker, 2007)'
_computing_data_reduction        'SAINT+  V7.46A (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSHELL v4.02 (Bruker, 2000)'
_computing_publication_material  'XCIF v6.12 (Bruker, 2001)'

_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)+(0.0293P)²+1.0873P] 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         3525
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0262
_refine_ls_wR_factor_ref         0.0692
_refine_ls_wR_factor_gt          0.0662
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.003
_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 1.160689(13) 0.65197(2) 1.014224(15) 0.05789(7) Uani 1 1 d . . .
Cl1 Cl 0.59068(5) 0.16099(8) 0.34073(6) 0.05430(15) Uani 1 1 d . . .
N1 N 0.61679(15) 0.4706(3) 0.48185(19) 0.0530(5) Uani 1 1 d . . .
H1 H 0.6068 0.3791 0.4436 0.064 Uiso 1 1 calc R . .
C1 C 0.6591(2) 0.4646(3) 0.5938(2) 0.0545(6) Uani 1 1 d . . .
H1A H 0.6764 0.3620 0.6296 0.065 Uiso 1 1 calc R . .
C2 C 0.6771(2) 0.6085(3) 0.6563(2) 0.0498(5) Uani 1 1 d . . .
H2 H 0.7064 0.6036 0.7345 0.060 Uiso 1 1 calc R . .
C3 C 0.65150(16) 0.7621(3) 0.60282(18) 0.0411(4) Uani 1 1 d . . .
C4 C 0.60575(17) 0.7620(3) 0.4859(2) 0.0481(5) Uani 1 1 d . . .
H4 H 0.5863 0.8621 0.4475 0.058 Uiso 1 1 calc R . .
C5 C 0.58962(18) 0.6145(4) 0.4277(2) 0.0550(6) Uani 1 1 d . . .
H5 H 0.5594 0.6147 0.3497 0.066 Uiso 1 1 calc R . .
C6 C 0.66460(18) 0.9208(3) 0.6659(2) 0.0482(5) Uani 1 1 d . . .
H6 H 0.6155 1.0008 0.6378 0.058 Uiso 1 1 calc R . .
C7 C 0.73750(18) 0.9644(3) 0.7579(2) 0.0496(5) Uani 1 1 d . . .
H7 H 0.7281 1.0650 0.7909 0.060 Uiso 1 1 calc R . .
C8 C 0.83101(17) 0.8766(3) 0.8151(2) 0.0447(5) Uani 1 1 d . . .
C9 C 0.8906(2) 0.8070(4) 0.7552(2) 0.0613(7) Uani 1 1 d . . .
H9 H 0.8685 0.8075 0.6763 0.074 Uiso 1 1 calc R . .
C10 C 0.9822(2) 0.7370(5) 0.8109(2) 0.0644(8) Uani 1 1 d . . .
H10 H 1.0211 0.6913 0.7694 0.077 Uiso 1 1 calc R . .
C11 C 1.01596(18) 0.7349(3) 0.9282(2) 0.0479(5) Uani 1 1 d . . .
C12 C 0.9574(2) 0.8011(4) 0.9884(2) 0.0567(6) Uani 1 1 d . . .
H12 H 0.9794 0.7987 1.0673 0.068 Uiso 1 1 calc R . .
C13 C 0.86627(19) 0.8713(4) 0.9328(2) 0.0541(6) Uani 1 1 d . . .
H13 H 0.8277 0.9158 0.9749 0.065 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 0.05064(11) 0.05956(12) 0.05504(11) -0.00106(7) 0.00321(7) -0.00068(7)
Cl1 0.0501(3) 0.0517(3) 0.0542(3) -0.0130(3) 0.0054(3) -0.0065(2)
N1 0.0458(11) 0.0586(12) 0.0565(12) -0.0195(10) 0.0181(9) -0.0106(9)
C1 0.0595(15) 0.0458(13) 0.0580(14) -0.0001(11) 0.0171(12) -0.0056(11)
C2 0.0571(14) 0.0493(12) 0.0400(11) 0.0016(10) 0.0100(10) -0.0040(11)
C3 0.0350(10) 0.0453(11) 0.0419(10) -0.0007(9) 0.0098(8) -0.0019(8)
C4 0.0392(11) 0.0582(14) 0.0430(11) 0.0065(10) 0.0065(9) 0.0044(10)
C5 0.0401(12) 0.0822(18) 0.0398(11) -0.0086(12) 0.0079(9) -0.0044(12)
C6 0.0441(12) 0.0432(12) 0.0563(13) -0.0020(10) 0.0136(10) 0.0015(9)
C7 0.0464(12) 0.0476(12) 0.0567(13) -0.0128(11) 0.0183(10) -0.0034(10)
C8 0.0417(11) 0.0474(12) 0.0453(11) -0.0108(9) 0.0135(9) -0.0086(9)
C9 0.0530(14) 0.093(2) 0.0364(11) -0.0087(12) 0.0115(10) 0.0127(14)
C10 0.0539(14) 0.096(2) 0.0422(12) -0.0126(14) 0.0125(11) 0.0150(15)
C11 0.0427(11) 0.0538(13) 0.0434(11) -0.0044(10) 0.0073(9) -0.0081(10)
C12 0.0531(14) 0.0806(18) 0.0365(11) -0.0056(12) 0.0139(10) -0.0123(13)
C13 0.0467(13) 0.0744(17) 0.0454(12) -0.0147(12) 0.0201(10) -0.0102(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 C11 2.103(2) . ?
N1 C5 1.329(4) . ?
N1 C1 1.332(3) . ?
C1 C2 1.368(4) . ?
C2 C3 1.392(3) . ?
C3 C4 1.394(3) . ?
C3 C6 1.473(3) . ?
C4 C5 1.365(4) . ?
C6 C7 1.328(3) . ?
C7 C8 1.473(4) . ?
C8 C13 1.389(3) . ?
C8 C9 1.392(3) . ?
C9 C10 1.385(4) . ?
C10 C11 1.382(3) . ?
C11 C12 1.373(4) . ?
C12 C13 1.380(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
C5 N1 C1 121.7(2) . . ?
N1 C1 C2 120.3(2) . . ?
C1 C2 C3 119.9(2) . . ?
C2 C3 C4 117.7(2) . . ?
C2 C3 C6 122.5(2) . . ?
C4 C3 C6 119.7(2) . . ?
C5 C4 C3 119.9(2) . . ?
N1 C5 C4 120.5(2) . . ?
C7 C6 C3 128.4(2) . . ?
C6 C7 C8 129.4(2) . . ?
C13 C8 C9 117.5(2) . . ?
C13 C8 C7 120.2(2) . . ?
C9 C8 C7 122.1(2) . . ?
C10 C9 C8 121.3(2) . . ?
C11 C10 C9 120.0(2) . . ?
C12 C11 C10 119.4(2) . . ?
C12 C11 I1 119.81(18) . . ?
C10 C11 I1 120.56(19) . . ?
C11 C12 C13 120.5(2) . . ?
C12 C13 C8 121.3(2) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.019
_refine_diff_density_min         -0.701
_refine_diff_density_rms         0.057
_database_code_depnum_ccdc_archive 'CCDC 1008125'
