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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_9-F

_audit_creation_date             2013-07-16T17:12:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C13 H9 F N 1+, Br 1-, H2 O'
_chemical_formula_sum            'C13 H11 Br F N O'
_chemical_formula_weight         296.14

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

_cell_length_a                   10.4896(4)
_cell_length_b                   12.9381(5)
_cell_length_c                   9.9423(3)
_cell_angle_alpha                90
_cell_angle_beta                 117.876(3)
_cell_angle_gamma                90
_cell_volume                     1192.75(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    270(2)
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      25.35
_cell_measurement_reflns_used    6927


#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.623
_exptl_absorpt_correction_T_max  0.719
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      270(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_number            9072
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.84
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_reflns_number_total             2153
_reflns_number_gt                1406
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0528P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2153
_refine_ls_number_parameters     170
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1032
_refine_ls_wR_factor_gt          0.0988
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.748
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.054

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.27235(5) 0.10783(3) 0.32507(5) 0.0754(2) Uani 1 1 d . . .
C5A C 0.2750(4) 0.1244(2) 0.8979(4) 0.0612(8) Uani 0.5 1 d P A 1
N1A N 0.2740(4) 0.1242(2) 0.7565(4) 0.0619(9) Uani 0.5 1 d P A 1
C9A C 0.7889(5) 0.1450(3) 1.1524(5) 0.0719(10) Uani 0.5 1 d P A 1
F1A F 0.9097(5) 0.1512(5) 1.2713(6) 0.1072(16) Uani 0.5 1 d P A 1
C10A C 0.7881(4) 0.1438(3) 1.0091(5) 0.0700(11) Uani 0.5 1 d P A 1
H10A H 0.8753 0.1474 1.0062 0.084 Uiso 0.5 1 calc PR A 1
N1B N 0.2750(4) 0.1244(2) 0.8979(4) 0.0612(8) Uani 0.5 1 d P A 2
C5B C 0.2740(4) 0.1242(2) 0.7565(4) 0.0619(9) Uani 0.5 1 d P A 2
C9B C 0.7881(4) 0.1438(3) 1.0091(5) 0.0700(11) Uani 0.5 1 d P A 2
C10B C 0.7889(5) 0.1450(3) 1.1524(5) 0.0719(10) Uani 0.5 1 d P A 2
H10B H 0.8762 0.1489 1.2413 0.086 Uiso 0.5 1 calc PR A 2
F1B F 0.9135(5) 0.1490(5) 1.0139(6) 0.1109(17) Uani 0.5 1 d P A 2
C6 C 0.4031(4) 0.1300(2) 1.0285(4) 0.0599(9) Uani 1 1 d . . .
H6 H 0.4022 0.1304 1.1216 0.072 Uiso 1 1 calc R A 1
C4 C 0.1426(5) 0.1178(3) 0.9002(5) 0.0714(11) Uani 1 1 d . . .
H4 H 0.1416 0.1178 0.9932 0.086 Uiso 1 1 calc R A 1
C1 C 0.1413(5) 0.1192(3) 0.6243(5) 0.0748(11) Uani 1 1 d . . .
H1 H 0.1406 0.1203 0.5305 0.09 Uiso 1 1 calc R A 1
C13 C 0.4027(4) 0.1288(2) 0.7528(4) 0.0626(10) Uani 1 1 d . . .
H13 H 0.4022 0.1276 0.659 0.075 Uiso 1 1 calc R A 1
C8 C 0.6653(4) 0.1406(3) 1.1608(4) 0.0646(10) Uani 1 1 d . . .
H8 H 0.6667 0.1412 1.2551 0.078 Uiso 1 1 calc R A 1
C7 C 0.5339(4) 0.1351(2) 1.0272(4) 0.0523(9) Uani 1 1 d . A .
C3 C 0.0176(5) 0.1115(3) 0.7715(5) 0.0822(12) Uani 1 1 d . A .
H3 H -0.0684 0.1061 0.7766 0.099 Uiso 1 1 calc R . .
C2 C 0.0150(5) 0.1128(3) 0.6272(6) 0.0858(13) Uani 1 1 d . A .
H2 H -0.0716 0.1093 0.5376 0.103 Uiso 1 1 calc R . .
C12 C 0.5332(4) 0.1349(2) 0.8833(4) 0.0579(9) Uani 1 1 d . A .
C11 C 0.6669(4) 0.1378(3) 0.8800(5) 0.0692(10) Uani 1 1 d . . .
H11 H 0.6691 0.1355 0.7877 0.083 Uiso 1 1 calc R A 1
O1 O 0.6343(4) 0.1134(2) 0.4850(5) 0.0995(11) Uani 1 1 d D . .
H1O H 0.552(4) 0.099(3) 0.425(6) 0.119 Uiso 1 1 d D . .
H2O H 0.656(4) 0.063(3) 0.539(5) 0.119 Uiso 1 1 d D . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C5A C6 1.366(5) . ?
C5A N1A 1.401(5) . ?
C5A C4 1.401(5) . ?
N1A C13 1.370(5) . ?
N1A C1 1.399(6) . ?
C9A F1A 1.268(6) . ?
C9A C8 1.340(6) . ?
C9A C10A 1.421(5) . ?
C10A C11 1.321(5) . ?
C10A H10A 0.93 . ?
C6 C7 1.380(5) . ?
C6 H6 0.93 . ?
C4 C3 1.339(6) . ?
C4 H4 0.93 . ?
C1 C2 1.341(6) . ?
C1 H1 0.93 . ?
C13 C12 1.380(5) . ?
C13 H13 0.93 . ?
C8 C7 1.399(5) . ?
C8 H8 0.93 . ?
C7 C12 1.427(5) . ?
C3 C2 1.422(6) . ?
C3 H3 0.93 . ?
C2 H2 0.93 . ?
C12 C11 1.418(5) . ?
C11 H11 0.93 . ?
O1 H1O 0.81(4) . ?
O1 H2O 0.80(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
C6 C5A N1A 119.7(3) . . ?
C6 C5A C4 122.0(3) . . ?
N1A C5A C4 118.2(4) . . ?
C13 N1A C1 122.5(3) . . ?
C13 N1A C5A 118.8(3) . . ?
C1 N1A C5A 118.7(3) . . ?
F1A C9A C8 121.3(4) . . ?
F1A C9A C10A 118.0(4) . . ?
C8 C9A C10A 120.7(4) . . ?
C11 C10A C9A 121.8(4) . . ?
C11 C10A H10A 119.1 . . ?
C9A C10A H10A 119.1 . . ?
C5A C6 C7 122.3(3) . . ?
C5A C6 H6 118.8 . . ?
C7 C6 H6 118.8 . . ?
C3 C4 C5A 121.5(4) . . ?
C3 C4 H4 119.2 . . ?
C5A C4 H4 119.2 . . ?
C2 C1 N1A 122.8(4) . . ?
C2 C1 H1 118.6 . . ?
N1A C1 H1 118.6 . . ?
N1A C13 C12 122.3(3) . . ?
N1A C13 H13 118.8 . . ?
C12 C13 H13 118.8 . . ?
C9A C8 C7 119.7(4) . . ?
C9A C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C6 C7 C8 122.4(3) . . ?
C6 C7 C12 118.1(3) . . ?
C8 C7 C12 119.6(3) . . ?
C4 C3 C2 120.8(4) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C1 C2 C3 118.0(5) . . ?
C1 C2 H2 121 . . ?
C3 C2 H2 121 . . ?
C13 C12 C11 122.5(3) . . ?
C13 C12 C7 118.7(3) . . ?
C11 C12 C7 118.8(4) . . ?
C10A C11 C12 119.5(4) . . ?
C10A C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
H1O O1 H2O 101(3) . . ?








_database_code_depnum_ccdc_archive 'CCDC 975287'
#######################################################################
#
#                 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_9-Cl

_audit_creation_date             2014-08-24T22:48:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C13 H9 Cl N 1+, Br 1-, 0.75(H2 O)'
_chemical_formula_sum            'C13 H10.50 Br Cl N O0.75'
_chemical_formula_weight         308.08

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

_cell_length_a                   9.5818(3)
_cell_length_b                   11.4519(3)
_cell_length_c                   12.5667(4)
_cell_angle_alpha                109.027(2)
_cell_angle_beta                 94.230(2)
_cell_angle_gamma                105.253(2)
_cell_volume                     1238.29(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             614

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.418
_exptl_absorpt_correction_T_max  0.539
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_number            16387
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_reflns_number_total             4355
_reflns_number_gt                3284
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0429P)²+1.2826P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4355
_refine_ls_number_parameters     320
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.066
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1208
_refine_ls_wR_factor_gt          0.1107
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.053

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
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'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.12781(6) 0.99431(6) 0.69817(5) 0.0895(2) Uani 1 1 d . . .
Br2 Br 0.38376(6) 0.28677(5) 0.02205(5) 0.0862(2) Uani 1 1 d . . .
Cl1 Cl 0.36791(17) 0.63675(13) 0.65711(11) 0.0921(4) Uani 1 1 d . . .
Cl2 Cl 0.15360(18) 0.37854(14) 0.35998(13) 0.1026(5) Uani 1 1 d . . .
N1 N 0.4419(3) 0.9168(3) 0.2644(3) 0.0581(8) Uani 1 1 d . . .
N2 N 0.0534(3) 0.7472(3) 0.0619(3) 0.0621(9) Uani 1 1 d . . .
C7 C 0.5465(5) 0.7060(4) 0.4012(4) 0.0698(11) Uani 1 1 d . . .
H7 H 0.6163 0.681 0.359 0.084 Uiso 1 1 calc R . .
C20 C -0.0065(5) 0.7261(4) 0.1500(4) 0.0683(11) Uani 1 1 d . . .
H20 H -0.0775 0.7648 0.1764 0.082 Uiso 1 1 calc R . .
C6 C 0.5087(4) 0.8355(4) 0.2898(4) 0.0629(10) Uani 1 1 d . . .
H6 H 0.5796 0.8115 0.2483 0.075 Uiso 1 1 calc R . .
C27 C 0.0348(4) 0.6480(4) 0.2023(4) 0.0632(10) Uani 1 1 d . . .
C11 C 0.2997(4) 0.9077(4) 0.4121(4) 0.0627(10) Uani 1 1 d . . .
H11 H 0.2287 0.9324 0.453 0.075 Uiso 1 1 calc R . .
C25 C 0.2011(4) 0.6110(4) 0.0689(4) 0.0650(11) Uani 1 1 d . . .
H25 H 0.2716 0.5726 0.0408 0.078 Uiso 1 1 calc R . .
C10 C 0.3338(5) 0.7771(4) 0.5286(3) 0.0632(11) Uani 1 1 d . . .
H10 H 0.2635 0.7994 0.5716 0.076 Uiso 1 1 calc R . .
C13 C 0.4742(4) 0.7879(4) 0.3750(3) 0.0571(9) Uani 1 1 d . . .
C21 C -0.0280(5) 0.6263(5) 0.2960(4) 0.0830(14) Uani 1 1 d . . .
H21 H -0.0967 0.6667 0.3249 0.1 Uiso 1 1 calc R . .
C26 C 0.1598(4) 0.6904(4) 0.0193(4) 0.0612(10) Uani 1 1 d . . .
C14 C 0.3670(4) 0.8255(4) 0.4397(3) 0.0561(9) Uani 1 1 d . . .
C12 C 0.3349(4) 0.9544(4) 0.3250(4) 0.0600(10) Uani 1 1 d . . .
C28 C 0.1409(4) 0.5860(4) 0.1601(3) 0.0580(10) Uani 1 1 d . . .
C8 C 0.5148(5) 0.6635(4) 0.4880(4) 0.0714(11) Uani 1 1 d . . .
H8 H 0.5648 0.6116 0.5069 0.086 Uiso 1 1 calc R . .
C18 C 0.0065(5) 0.8252(4) 0.0102(4) 0.0733(12) Uani 1 1 d . . .
H18 H -0.0664 0.861 0.0371 0.088 Uiso 1 1 calc R . .
C4 C 0.4831(5) 0.9642(4) 0.1788(4) 0.0694(11) Uani 1 1 d . . .
H4 H 0.5547 0.9389 0.1391 0.083 Uiso 1 1 calc R . .
C1 C 0.2707(5) 1.0393(4) 0.2940(4) 0.0694(11) Uani 1 1 d . . .
H1 H 0.198 1.0648 0.3321 0.083 Uiso 1 1 calc R . .
C15 C 0.2169(5) 0.7170(5) -0.0733(4) 0.0707(11) Uani 1 1 d . . .
H15 H 0.2883 0.6808 -0.1028 0.085 Uiso 1 1 calc R . .
C22 C 0.0120(5) 0.5480(5) 0.3424(4) 0.0848(14) Uani 1 1 d . . .
H22 H -0.0282 0.5349 0.4042 0.102 Uiso 1 1 calc R . .
C3 C 0.4210(5) 1.0456(4) 0.1530(4) 0.0725(12) Uani 1 1 d . . .
H3 H 0.4507 1.0769 0.0961 0.087 Uiso 1 1 calc R . .
O2 O 0.6420(5) 0.5659(5) 0.1599(4) 0.1152(13) Uani 1 1 d D . .
H3O H 0.567(5) 0.502(5) 0.129(5) 0.173 Uiso 1 1 d D . .
H4O H 0.649(8) 0.610(6) 0.117(5) 0.173 Uiso 1 1 d D . .
C2 C 0.3118(5) 1.0844(5) 0.2108(4) 0.0774(13) Uani 1 1 d . . .
H2 H 0.2683 1.1404 0.192 0.093 Uiso 1 1 calc R . .
C16 C 0.1705(5) 0.7940(5) -0.1205(4) 0.0769(12) Uani 1 1 d . . .
H16 H 0.2094 0.8099 -0.1818 0.092 Uiso 1 1 calc R . .
C24 C 0.1806(5) 0.5028(4) 0.2109(4) 0.0677(11) Uani 1 1 d . . .
H24 H 0.2499 0.4617 0.1849 0.081 Uiso 1 1 calc R . .
C23 C 0.1142(5) 0.4851(5) 0.2987(4) 0.0764(12) Uani 1 1 d . . .
C17 C 0.0639(5) 0.8490(5) -0.0765(4) 0.0779(13) Uani 1 1 d . . .
H17 H 0.0326 0.9028 -0.108 0.093 Uiso 1 1 calc R . .
O1 O 0.8899(7) 0.8447(9) 0.4708(7) 0.136(3) Uani 0.5 1 d PD . .
H2O H 0.9508(17) 0.879(4) 0.5322(11) 0.204 Uiso 0.5 1 d PD . .
H1O H 0.902(4) 0.900(3) 0.440(3) 0.204 Uiso 0.5 1 d PD . .
C9 C 0.4059(5) 0.6984(4) 0.5493(4) 0.0669(11) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C9 1.740(4) . ?
Cl2 C23 1.743(5) . ?
N1 C6 1.362(5) . ?
N1 C4 1.392(5) . ?
N1 C12 1.397(5) . ?
N2 C20 1.345(5) . ?
N2 C26 1.397(5) . ?
N2 C18 1.403(6) . ?
C7 C8 1.354(6) . ?
C7 C13 1.407(6) . ?
C7 H7 0.93 . ?
C20 C27 1.385(6) . ?
C20 H20 0.93 . ?
C6 C13 1.375(6) . ?
C6 H6 0.93 . ?
C27 C21 1.424(6) . ?
C27 C28 1.426(6) . ?
C11 C14 1.386(6) . ?
C11 C12 1.393(6) . ?
C11 H11 0.93 . ?
C25 C26 1.378(6) . ?
C25 C28 1.396(6) . ?
C25 H25 0.93 . ?
C10 C9 1.347(6) . ?
C10 C14 1.421(6) . ?
C10 H10 0.93 . ?
C13 C14 1.424(5) . ?
C21 C22 1.334(7) . ?
C21 H21 0.93 . ?
C26 C15 1.408(6) . ?
C12 C1 1.415(6) . ?
C28 C24 1.418(6) . ?
C8 C9 1.406(6) . ?
C8 H8 0.93 . ?
C18 C17 1.329(7) . ?
C18 H18 0.93 . ?
C4 C3 1.338(6) . ?
C4 H4 0.93 . ?
C1 C2 1.349(7) . ?
C1 H1 0.93 . ?
C15 C16 1.354(7) . ?
C15 H15 0.93 . ?
C22 C23 1.404(7) . ?
C22 H22 0.93 . ?
C3 C2 1.402(6) . ?
C3 H3 0.93 . ?
O2 H3O 0.8401(10) . ?
O2 H4O 0.8401(11) . ?
C2 H2 0.93 . ?
C16 C17 1.393(7) . ?
C16 H16 0.93 . ?
C24 C23 1.359(6) . ?
C24 H24 0.93 . ?
C17 H17 0.93 . ?
O1 H2O 0.8400(11) . ?
O1 H1O 0.8400(11) . ?

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
C6 N1 C4 119.4(3) . . ?
C6 N1 C12 120.5(4) . . ?
C4 N1 C12 120.1(4) . . ?
C20 N2 C26 121.0(4) . . ?
C20 N2 C18 119.7(4) . . ?
C26 N2 C18 119.3(4) . . ?
C8 C7 C13 120.1(4) . . ?
C8 C7 H7 119.9 . . ?
C13 C7 H7 119.9 . . ?
N2 C20 C27 121.7(4) . . ?
N2 C20 H20 119.2 . . ?
C27 C20 H20 119.2 . . ?
N1 C6 C13 121.8(4) . . ?
N1 C6 H6 119.1 . . ?
C13 C6 H6 119.1 . . ?
C20 C27 C21 121.6(4) . . ?
C20 C27 C28 119.2(4) . . ?
C21 C27 C28 119.1(4) . . ?
C14 C11 C12 122.1(4) . . ?
C14 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
C26 C25 C28 122.4(4) . . ?
C26 C25 H25 118.8 . . ?
C28 C25 H25 118.8 . . ?
C9 C10 C14 118.7(4) . . ?
C9 C10 H10 120.6 . . ?
C14 C10 H10 120.6 . . ?
C6 C13 C7 120.9(4) . . ?
C6 C13 C14 119.4(4) . . ?
C7 C13 C14 119.7(4) . . ?
C22 C21 C27 119.9(5) . . ?
C22 C21 H21 120.1 . . ?
C27 C21 H21 120.1 . . ?
C25 C26 N2 118.4(4) . . ?
C25 C26 C15 124.0(4) . . ?
N2 C26 C15 117.6(4) . . ?
C11 C14 C10 123.2(4) . . ?
C11 C14 C13 117.9(4) . . ?
C10 C14 C13 118.9(4) . . ?
C11 C12 N1 118.3(4) . . ?
C11 C12 C1 124.5(4) . . ?
N1 C12 C1 117.2(4) . . ?
C25 C28 C24 123.0(4) . . ?
C25 C28 C27 117.4(4) . . ?
C24 C28 C27 119.7(4) . . ?
C7 C8 C9 119.6(4) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C17 C18 N2 121.4(4) . . ?
C17 C18 H18 119.3 . . ?
N2 C18 H18 119.3 . . ?
C3 C4 N1 120.8(4) . . ?
C3 C4 H4 119.6 . . ?
N1 C4 H4 119.6 . . ?
C2 C1 C12 122.0(4) . . ?
C2 C1 H1 119 . . ?
C12 C1 H1 119 . . ?
C16 C15 C26 121.7(4) . . ?
C16 C15 H15 119.1 . . ?
C26 C15 H15 119.1 . . ?
C21 C22 C23 120.7(5) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C4 C3 C2 120.8(4) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
H3O O2 H4O 105.8(3) . . ?
C1 C2 C3 119.0(5) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C15 C16 C17 119.5(5) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C23 C24 C28 117.8(4) . . ?
C23 C24 H24 121.1 . . ?
C28 C24 H24 121.1 . . ?
C24 C23 C22 122.8(5) . . ?
C24 C23 Cl2 119.6(4) . . ?
C22 C23 Cl2 117.6(4) . . ?
C18 C17 C16 120.5(5) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
H2O O1 H1O 105.8(3) . . ?
C10 C9 C8 122.9(4) . . ?
C10 C9 Cl1 120.1(3) . . ?
C8 C9 Cl1 117.0(4) . . ?





_database_code_depnum_ccdc_archive 'CCDC 975288'
#######################################################################
#
#                 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_9-Br

_audit_creation_date             2014-08-24T23:15:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C13 H9 Br N 1+, Br 1-, H2 O'
_chemical_formula_sum            'C13 H11 Br2 N O'
_chemical_formula_weight         357.05

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

_cell_length_a                   7.3152(6)
_cell_length_b                   9.7141(9)
_cell_length_c                   10.352(2)
_cell_angle_alpha                68.687(3)
_cell_angle_beta                 86.209(3)
_cell_angle_gamma                68.298(4)
_cell_volume                     634.75(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      25.35
_cell_measurement_reflns_used    34425

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.868
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    6.367
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.726
_exptl_absorpt_correction_T_max  0.904
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0939
_diffrn_reflns_number            4583
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_reflns_number_total             2194
_reflns_number_gt                1177
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0973P)²+6.2379P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2194
_refine_ls_number_parameters     160
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1223
_refine_ls_R_factor_gt           0.0799
_refine_ls_wR_factor_ref         0.2541
_refine_ls_wR_factor_gt          0.2424
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.067
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.154

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.1944(15) 0.6927(13) -0.1692(12) 0.059(3) Uani 1 1 d . . .
C13 C 0.1619(19) 0.6039(14) 0.0721(15) 0.052(3) Uani 1 1 d . . .
C10 C 0.282(2) 0.3204(16) 0.2142(16) 0.060(4) Uani 1 1 d . . .
H10 H 0.3411 0.2138 0.2243 0.072 Uiso 1 1 calc R . .
C8 C 0.124(2) 0.5180(16) 0.3152(15) 0.058(3) Uani 1 1 d . . .
H8 H 0.0793 0.5406 0.3942 0.069 Uiso 1 1 calc R . .
C12 C 0.2900(19) 0.5369(16) -0.1671(15) 0.060(4) Uani 1 1 d . . .
C11 C 0.317(2) 0.4140(16) -0.0395(16) 0.067(4) Uani 1 1 d . . .
H11 H 0.378 0.3097 -0.0356 0.08 Uiso 1 1 calc R . .
C14 C 0.257(2) 0.4394(14) 0.0828(15) 0.054(3) Uani 1 1 d . . .
C7 C 0.094(2) 0.6343(17) 0.1948(15) 0.058(3) Uani 1 1 d . . .
H7 H 0.0276 0.7388 0.1892 0.07 Uiso 1 1 calc R . .
C2 C 0.313(2) 0.632(2) -0.4092(18) 0.073(4) Uani 1 1 d . . .
H2 H 0.3475 0.6147 -0.4915 0.088 Uiso 1 1 calc R . .
C1 C 0.346(2) 0.5103(17) -0.2907(16) 0.064(4) Uani 1 1 d . . .
H1 H 0.405 0.4069 -0.2892 0.076 Uiso 1 1 calc R . .
C6 C 0.1339(19) 0.7209(14) -0.0534(15) 0.056(3) Uani 1 1 d . . .
H6 H 0.0698 0.8259 -0.0598 0.067 Uiso 1 1 calc R . .
C9 C 0.221(2) 0.3598(15) 0.3261(15) 0.058(3) Uani 1 1 d . . .
C4 C 0.171(2) 0.8146(17) -0.2961(17) 0.071(4) Uani 1 1 d . . .
H4 H 0.1128 0.919 -0.3001 0.085 Uiso 1 1 calc R . .
C3 C 0.227(2) 0.7895(18) -0.4120(17) 0.070(4) Uani 1 1 d . . .
H3 H 0.2095 0.8751 -0.4952 0.084 Uiso 1 1 calc R . .
O1 O 0.2989(18) 0.9950(15) -0.1361(14) 0.098(4) Uani 1 1 d D . .
H1O H 0.400(6) 1.017(3) -0.157(18) 0.146 Uiso 1 1 d D . .
H2O H 0.29(2) 0.975(4) -0.050(2) 0.146 Uiso 1 1 d D . .
Br1 Br 0.2965(2) 0.91896(18) 0.20394(18) 0.0759(6) Uani 1 1 d D . .
Br2 Br 0.2668(3) 0.2019(2) 0.50812(18) 0.0853(7) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.337(17) . ?
N1 C4 1.381(18) . ?
N1 C12 1.406(16) . ?
C13 C6 1.346(18) . ?
C13 C7 1.424(19) . ?
C13 C14 1.452(17) . ?
C10 C9 1.347(19) . ?
C10 C14 1.398(19) . ?
C10 H10 0.93 . ?
C8 C7 1.306(18) . ?
C8 C9 1.400(18) . ?
C8 H8 0.93 . ?
C12 C11 1.39(2) . ?
C12 C1 1.40(2) . ?
C11 C14 1.39(2) . ?
C11 H11 0.93 . ?
C7 H7 0.93 . ?
C2 C1 1.32(2) . ?
C2 C3 1.41(2) . ?
C2 H2 0.93 . ?
C1 H1 0.93 . ?
C6 H6 0.93 . ?
C9 Br2 1.902(14) . ?
C4 C3 1.32(2) . ?
C4 H4 0.93 . ?
C3 H3 0.93 . ?
O1 H1O 0.839(10) . ?
O1 H2O 0.841(10) . ?

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
C6 N1 C4 121.9(11) . . ?
C6 N1 C12 121.5(12) . . ?
C4 N1 C12 116.5(12) . . ?
C6 C13 C7 122.6(12) . . ?
C6 C13 C14 119.1(13) . . ?
C7 C13 C14 118.3(13) . . ?
C9 C10 C14 120.1(12) . . ?
C9 C10 H10 120 . . ?
C14 C10 H10 120 . . ?
C7 C8 C9 120.5(14) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C11 C12 C1 122.7(13) . . ?
C11 C12 N1 116.8(12) . . ?
C1 C12 N1 120.4(13) . . ?
C12 C11 C14 123.0(12) . . ?
C12 C11 H11 118.5 . . ?
C14 C11 H11 118.5 . . ?
C11 C14 C10 125.4(12) . . ?
C11 C14 C13 116.8(12) . . ?
C10 C14 C13 117.8(13) . . ?
C8 C7 C13 121.1(13) . . ?
C8 C7 H7 119.4 . . ?
C13 C7 H7 119.4 . . ?
C1 C2 C3 120.5(15) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C1 C12 119.8(14) . . ?
C2 C1 H1 120.1 . . ?
C12 C1 H1 120.1 . . ?
N1 C6 C13 122.8(12) . . ?
N1 C6 H6 118.6 . . ?
C13 C6 H6 118.6 . . ?
C10 C9 C8 122.1(13) . . ?
C10 C9 Br2 121.4(10) . . ?
C8 C9 Br2 116.5(11) . . ?
C3 C4 N1 123.0(13) . . ?
C3 C4 H4 118.5 . . ?
N1 C4 H4 118.5 . . ?
C4 C3 C2 119.7(15) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
H1O O1 H2O 106(3) . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF


_database_code_depnum_ccdc_archive 'CCDC 975289'
#######################################################################
#
#                 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_9-I-Br

_audit_creation_date             2014-08-24T23:53:21-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C13 H9 I N 1+, Br 1-, H2 O'
_chemical_formula_sum            'C13 H11 Br1 I1 N1 O1'
_chemical_formula_weight         404.01

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

_cell_length_a                   7.5841(6)
_cell_length_b                   19.2894(16)
_cell_length_c                   9.3211(9)
_cell_angle_alpha                90
_cell_angle_beta                 105.886(4)
_cell_angle_gamma                90
_cell_volume                     1311.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      22.46
_cell_measurement_reflns_used    18130

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    2.046
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    5.471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.388
_exptl_absorpt_correction_T_max  0.441
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.1114
_diffrn_reflns_av_unetI/netI     0.0704
_diffrn_reflns_number            6457
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.51
_diffrn_reflns_theta_max         22.49
_diffrn_reflns_theta_full        22.49
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_reflns_number_total             1676
_reflns_number_gt                1252
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0328P)²+3.1895P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1676
_refine_ls_number_parameters     160
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.117
_refine_ls_wR_factor_gt          0.1057
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.108

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
Br Br -0.2901 2.4595 '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'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.2855(11) 1.0937(4) 0.5590(8) 0.053(2) Uani 1 1 d . . .
C10 C 0.2246(15) 0.8812(5) 0.4540(11) 0.058(3) Uani 1 1 d . . .
H10 H 0.1507 0.8659 0.3627 0.07 Uiso 1 1 calc R . .
C14 C 0.2433(12) 0.9531(5) 0.4850(9) 0.044(2) Uani 1 1 d . . .
C2 C 0.1140(14) 1.1946(5) 0.3573(12) 0.062(3) Uani 1 1 d . . .
H2 H 0.0581 1.2287 0.2895 0.074 Uiso 1 1 calc R . .
C12 C 0.1772(13) 1.0731(5) 0.4180(10) 0.051(2) Uani 1 1 d . . .
C6 C 0.3720(13) 1.0453(5) 0.6571(10) 0.051(2) Uani 1 1 d . . .
H6 H 0.4448 1.0595 0.7497 0.062 Uiso 1 1 calc R . .
C8 C 0.4305(14) 0.8570(6) 0.6999(10) 0.063(3) Uani 1 1 d . . .
H8 H 0.4917 0.8246 0.77 0.075 Uiso 1 1 calc R . .
C4 C 0.3034(14) 1.1631(5) 0.5968(12) 0.061(3) Uani 1 1 d . . .
H4 H 0.3738 1.1757 0.6915 0.073 Uiso 1 1 calc R . .
C3 C 0.2217(15) 1.2131(5) 0.5002(12) 0.063(3) Uani 1 1 d . . .
H3 H 0.2365 1.2595 0.528 0.075 Uiso 1 1 calc R . .
C13 C 0.3567(13) 0.9754(5) 0.6253(9) 0.049(2) Uani 1 1 d . . .
C1 C 0.0926(16) 1.1278(5) 0.3195(11) 0.068(3) Uani 1 1 d . . .
H1 H 0.0194 1.1163 0.225 0.082 Uiso 1 1 calc R . .
C9 C 0.3147(13) 0.8344(5) 0.5578(10) 0.054(3) Uani 1 1 d . . .
C11 C 0.1564(14) 1.0042(5) 0.3829(10) 0.056(3) Uani 1 1 d . . .
H11 H 0.0833 0.9909 0.2896 0.068 Uiso 1 1 calc R . .
C7 C 0.4494(14) 0.9250(6) 0.7303(10) 0.061(3) Uani 1 1 d . . .
H7 H 0.5245 0.9395 0.8219 0.073 Uiso 1 1 calc R . .
O1 O 0.2484(11) 0.5638(4) 0.5370(10) 0.080(2) Uani 1 1 d D . .
H1O H 0.231(16) 0.525(3) 0.494(13) 0.119 Uiso 1 1 d D . .
H2O H 0.162(11) 0.568(6) 0.576(13) 0.119 Uiso 1 1 d D . .
I1 I 0.28806(11) 0.72802(4) 0.52574(8) 0.0701(3) Uani 1 1 d . . .
Br2 Br 0.16582(17) 1.39943(6) 0.41899(11) 0.0702(4) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.345(11) . ?
N1 C4 1.382(12) . ?
N1 C12 1.403(11) . ?
C10 C9 1.362(13) . ?
C10 C14 1.417(13) . ?
C10 H10 0.93 . ?
C14 C11 1.402(12) . ?
C14 C13 1.421(12) . ?
C2 C1 1.334(13) . ?
C2 C3 1.405(14) . ?
C2 H2 0.93 . ?
C12 C11 1.369(13) . ?
C12 C1 1.430(13) . ?
C6 C13 1.377(12) . ?
C6 H6 0.93 . ?
C8 C7 1.342(13) . ?
C8 C9 1.442(13) . ?
C8 H8 0.93 . ?
C4 C3 1.350(13) . ?
C4 H4 0.93 . ?
C3 H3 0.93 . ?
C13 C7 1.422(13) . ?
C1 H1 0.93 . ?
C9 I1 2.076(10) . ?
C11 H11 0.93 . ?
C7 H7 0.93 . ?
O1 H1O 0.839(10) . ?
O1 H2O 0.840(11) . ?

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
C6 N1 C4 120.2(8) . . ?
C6 N1 C12 119.5(8) . . ?
C4 N1 C12 120.3(8) . . ?
C9 C10 C14 120.1(9) . . ?
C9 C10 H10 120 . . ?
C14 C10 H10 120 . . ?
C11 C14 C10 123.2(8) . . ?
C11 C14 C13 117.8(9) . . ?
C10 C14 C13 119.0(9) . . ?
C1 C2 C3 119.6(10) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C11 C12 N1 119.9(8) . . ?
C11 C12 C1 124.1(9) . . ?
N1 C12 C1 116.0(9) . . ?
N1 C6 C13 122.4(9) . . ?
N1 C6 H6 118.8 . . ?
C13 C6 H6 118.8 . . ?
C7 C8 C9 119.5(9) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C3 C4 N1 121.8(10) . . ?
C3 C4 H4 119.1 . . ?
N1 C4 H4 119.1 . . ?
C4 C3 C2 119.5(10) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C6 C13 C14 119.2(9) . . ?
C6 C13 C7 121.6(9) . . ?
C14 C13 C7 119.2(9) . . ?
C2 C1 C12 122.8(10) . . ?
C2 C1 H1 118.6 . . ?
C12 C1 H1 118.6 . . ?
C10 C9 C8 120.9(10) . . ?
C10 C9 I1 122.9(7) . . ?
C8 C9 I1 116.2(7) . . ?
C12 C11 C14 121.2(8) . . ?
C12 C11 H11 119.4 . . ?
C14 C11 H11 119.4 . . ?
C8 C7 C13 121.3(9) . . ?
C8 C7 H7 119.3 . . ?
C13 C7 H7 119.3 . . ?
H1O O1 H2O 105(3) . . ?

_vrf_THETM01_ALERT_3_A           
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
            Calculated sin(theta_max)/wavelength =    0.5382
RESPONSE: The best-quality dataset was reported. The single crystals
were small in size and diffracted poorly despite the presence of
heavy atoms).
;

_vrf_PLAT023_ALERT_3_A           
;
PROBLEM: Resolution (too) Low [sin(theta)/Lambda < 0.6]..  22.49 Deg.  
RESPONSE: The dataset of best quality was reported. The single crystals
were small in size and diffracted poorly (despite the presence of
heavy atoms).
;

_vrf_PLAT023_ALERT_3_C           
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......   0.978 Note   
RESPONSE: The dataset of best quality was reported. The single crystals
were small in size and diffracted poorly (despite the presence of
heavy atoms).
;




_database_code_depnum_ccdc_archive 'CCDC 975290'
#######################################################################
#
#                 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_9-I-I3

_audit_creation_date             2013-07-14T20:49:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C13 H9 I N 1+, I3 1-'
_chemical_formula_sum            'C13 H9 I4 N'
_chemical_formula_weight         686.81

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

_cell_length_a                   7.5081(3)
_cell_length_b                   10.4940(5)
_cell_length_c                   11.7322(6)
_cell_angle_alpha                105.219(2)
_cell_angle_beta                 105.581(2)
_cell_angle_gamma                101.791(2)
_cell_volume                     820.76(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      25.35
_cell_measurement_reflns_used    12875

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    2.779
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             612


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    7.577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3425
_exptl_absorpt_correction_T_max  0.7032
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_number            9366
_diffrn_reflns_av_R_equivalents  0.0924
_diffrn_reflns_av_sigmaI/netI    0.0704
_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2862
_reflns_number_gt                2069
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1022P)²+83.7239P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0063(14)
_refine_ls_number_reflns         2866
_refine_ls_number_parameters     164
_refine_ls_number_restraints     108
_refine_ls_R_factor_all          0.1399
_refine_ls_R_factor_gt           0.1155
_refine_ls_wR_factor_ref         0.3512
_refine_ls_wR_factor_gt          0.3405
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         2.454
_refine_diff_density_min         -1.340
_refine_diff_density_rms         0.363

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
I3 I 0.7861(3) 0.6178(2) 0.4608(2) 0.0595(7) Uani 1 1 d U . .
I2 I 0.5822(4) 0.4677(3) 0.2005(3) 0.0875(10) Uani 1 1 d U . .
I4 I 0.9851(4) 0.7753(3) 0.7283(2) 0.0781(9) Uani 1 1 d U . .
I1 I 1.0962(4) 0.2784(3) 0.9531(2) 0.0888(10) Uani 1 1 d U . .
N1 N 0.537(3) 0.087(3) 0.310(2) 0.054(6) Uani 1 1 d U . .
C11 C 0.722(4) -0.011(3) 0.448(3) 0.045(6) Uani 1 1 d U . .
H11 H 0.7674 -0.0849 0.4583 0.054 Uiso 1 1 calc R . .
C4 C 0.422(4) 0.076(3) 0.192(3) 0.056(7) Uani 1 1 d U . .
H4 H 0.3786 0.1494 0.1804 0.067 Uiso 1 1 calc R . .
C2 C 0.448(5) -0.157(4) 0.110(4) 0.072(9) Uani 1 1 d U . .
H2 H 0.4233 -0.2339 0.0404 0.087 Uiso 1 1 calc R . .
C13 C 0.700(4) 0.219(3) 0.528(3) 0.049(6) Uani 1 1 d U . .
C6 C 0.589(4) 0.208(3) 0.412(3) 0.052(7) Uani 1 1 d U . .
H6 H 0.5464 0.2819 0.3995 0.062 Uiso 1 1 calc R . .
C14 C 0.775(4) 0.111(3) 0.557(3) 0.053(7) Uani 1 1 d U . .
C12 C 0.609(4) -0.025(3) 0.330(3) 0.056(7) Uani 1 1 d U . .
C8 C 0.861(5) 0.355(3) 0.749(3) 0.059(7) Uani 1 1 d U . .
H8 H 0.8924 0.4365 0.8159 0.070 Uiso 1 1 calc R . .
C10 C 0.893(5) 0.130(4) 0.675(3) 0.068(9) Uani 1 1 d U . .
H10 H 0.9480 0.0623 0.6913 0.082 Uiso 1 1 calc R . .
C7 C 0.746(4) 0.346(3) 0.630(3) 0.056(7) Uani 1 1 d U . .
H7 H 0.7003 0.4185 0.6166 0.067 Uiso 1 1 calc R . .
C3 C 0.373(6) -0.044(4) 0.092(4) 0.083(10) Uani 1 1 d U . .
H3 H 0.2905 -0.0526 0.0140 0.099 Uiso 1 1 calc R . .
C9 C 0.927(4) 0.250(3) 0.770(3) 0.056(7) Uani 1 1 d U . .
C1 C 0.549(6) -0.151(4) 0.221(4) 0.077(10) Uani 1 1 d U . .
H1 H 0.5845 -0.2282 0.2309 0.092 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I3 I2 2.851(3) . ?
I3 I4 2.926(3) . ?
I1 C9 2.09(3) . ?
N1 C4 1.38(4) . ?
N1 C6 1.39(4) . ?
N1 C12 1.43(4) . ?
C11 C12 1.36(4) . ?
C11 C14 1.45(4) . ?
C11 H11 0.9300 . ?
C4 C3 1.38(5) . ?
C4 H4 0.9300 . ?
C2 C1 1.30(5) . ?
C2 C3 1.45(5) . ?
C2 H2 0.9300 . ?
C13 C6 1.35(4) . ?
C13 C7 1.43(4) . ?
C13 C14 1.44(4) . ?
C6 H6 0.9300 . ?
C14 C10 1.37(5) . ?
C12 C1 1.47(5) . ?
C8 C9 1.35(4) . ?
C8 C7 1.40(4) . ?
C8 H8 0.9300 . ?
C10 C9 1.36(5) . ?
C10 H10 0.9300 . ?
C7 H7 0.9300 . ?
C3 H3 0.9300 . ?
C1 H1 0.9300 . ?

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
I2 I3 I4 178.20(11) . . ?
C4 N1 C6 121(3) . . ?
C4 N1 C12 121(3) . . ?
C6 N1 C12 118(2) . . ?
C12 C11 C14 124(3) . . ?
C12 C11 H11 118.1 . . ?
C14 C11 H11 118.1 . . ?
C3 C4 N1 120(3) . . ?
C3 C4 H4 119.8 . . ?
N1 C4 H4 119.8 . . ?
C1 C2 C3 121(4) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C6 C13 C7 119(3) . . ?
C6 C13 C14 124(3) . . ?
C7 C13 C14 118(3) . . ?
C13 C6 N1 121(3) . . ?
C13 C6 H6 119.3 . . ?
N1 C6 H6 119.3 . . ?
C10 C14 C13 121(3) . . ?
C10 C14 C11 126(3) . . ?
C13 C14 C11 113(3) . . ?
C11 C12 N1 120(3) . . ?
C11 C12 C1 124(3) . . ?
N1 C12 C1 117(3) . . ?
C9 C8 C7 122(3) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C9 C10 C14 119(3) . . ?
C9 C10 H10 120.4 . . ?
C14 C10 H10 120.4 . . ?
C8 C7 C13 118(3) . . ?
C8 C7 H7 121.1 . . ?
C13 C7 H7 121.1 . . ?
C4 C3 C2 120(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C8 C9 C10 122(3) . . ?
C8 C9 I1 118(2) . . ?
C10 C9 I1 120(2) . . ?
C2 C1 C12 121(4) . . ?
C2 C1 H1 119.4 . . ?
C12 C1 H1 119.4 . . ?








_database_code_depnum_ccdc_archive 'CCDC 975291'
#######################################################################
#
#                 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_9-CH3

_audit_creation_date             2013-07-14T19:15:35-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C14 H12 N 1+, Br 1-, H2 O'
_chemical_formula_sum            'C14 H14 Br N O'
_chemical_formula_weight         292.17

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

_cell_length_a                   7.7990(10)
_cell_length_b                   9.585(2)
_cell_length_c                   9.664(2)
_cell_angle_alpha                68.967(7)
_cell_angle_beta                 70.925(6)
_cell_angle_gamma                83.339(6)
_cell_volume                     637.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      25.35
_cell_measurement_reflns_used    15094

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5959
_exptl_absorpt_correction_T_max  0.8066
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_number            5002
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_sigmaI/netI    0.0755
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         25.03
_reflns_number_total             2188
_reflns_number_gt                1429
_reflns_threshold_expression     >2σ(I)
_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.969

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0954P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2188
_refine_ls_number_parameters     161
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0611
_refine_ls_wR_factor_ref         0.1689
_refine_ls_wR_factor_gt          0.1552
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.718
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.079


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.4010(6) 0.1603(6) 0.8037(5) 0.0680(12) Uani 1 1 d . . .
C7 C 0.2287(9) -0.2130(8) 0.8846(8) 0.0849(18) Uani 1 1 d . . .
H7 H 0.2722 -0.2227 0.7867 0.102 Uiso 1 1 calc R . .
C6 C 0.3652(7) 0.0343(7) 0.7859(6) 0.0718(15) Uani 1 1 d . . .
H6 H 0.4112 0.0258 0.6875 0.086 Uiso 1 1 calc R . .
C8 C 0.1316(8) -0.3240(7) 1.0068(8) 0.0819(17) Uani 1 1 d . . .
H8 H 0.1102 -0.4097 0.9911 0.098 Uiso 1 1 calc R . .
C4 C 0.5077(8) 0.2749(8) 0.6766(7) 0.0824(18) Uani 1 1 d . . .
H4 H 0.5530 0.2637 0.5794 0.099 Uiso 1 1 calc R . .
C3 C 0.5449(9) 0.3992(8) 0.6932(8) 0.0878(19) Uani 1 1 d . . .
H3 H 0.6149 0.4740 0.6078 0.105 Uiso 1 1 calc R . .
C13 C 0.2654(7) -0.0806(6) 0.9045(6) 0.0667(14) Uani 1 1 d . . .
C1 C 0.3792(8) 0.3083(7) 0.9632(7) 0.0749(15) Uani 1 1 d . . .
H1 H 0.3362 0.3213 1.0596 0.090 Uiso 1 1 calc R . .
C9 C 0.0597(8) -0.3161(7) 1.1597(7) 0.0742(15) Uani 1 1 d . . .
C14 C 0.1937(7) -0.0704(7) 1.0585(6) 0.0655(14) Uani 1 1 d . . .
C12 C 0.3378(7) 0.1728(7) 0.9510(6) 0.0667(14) Uani 1 1 d . . .
C2 C 0.4781(9) 0.4176(8) 0.8402(8) 0.0892(19) Uani 1 1 d . . .
H2 H 0.5026 0.5049 0.8516 0.107 Uiso 1 1 calc R . .
C10 C 0.0932(8) -0.1902(7) 1.1810(7) 0.0723(15) Uani 1 1 d . . .
H10 H 0.0479 -0.1836 1.2802 0.087 Uiso 1 1 calc R . .
C11 C 0.2358(7) 0.0589(6) 1.0734(6) 0.0658(14) Uani 1 1 d . . .
H11 H 0.1928 0.0691 1.1711 0.079 Uiso 1 1 calc R . .
C15 C -0.0443(10) -0.4464(8) 1.2937(8) 0.097(2) Uani 1 1 d . . .
H15A H -0.1022 -0.4159 1.3825 0.145 Uiso 1 1 calc R . .
H15B H 0.0378 -0.5270 1.3196 0.145 Uiso 1 1 calc R . .
H15C H -0.1346 -0.4790 1.2642 0.145 Uiso 1 1 calc R . .
O1 O 0.8379(9) 0.1596(8) 0.4539(9) 0.132(2) Uani 1 1 d D . .
H2O H 0.946(7) 0.147(13) 0.457(15) 0.197 Uiso 1 1 d D . .
H1O H 0.832(17) 0.068(5) 0.462(15) 0.197 Uiso 1 1 d D . .
Br1 Br 0.28330(8) 0.20318(7) 0.40594(7) 0.0871(4) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.351(7) . ?
N1 C12 1.390(6) . ?
N1 C4 1.409(7) . ?
C7 C8 1.341(9) . ?
C7 C13 1.423(8) . ?
C7 H7 0.9300 . ?
C6 C13 1.357(8) . ?
C6 H6 0.9300 . ?
C8 C9 1.425(9) . ?
C8 H8 0.9300 . ?
C4 C3 1.333(8) . ?
C4 H4 0.9300 . ?
C3 C2 1.413(9) . ?
C3 H3 0.9300 . ?
C13 C14 1.445(7) . ?
C1 C2 1.342(8) . ?
C1 C12 1.428(8) . ?
C1 H1 0.9300 . ?
C9 C10 1.362(8) . ?
C9 C15 1.511(9) . ?
C14 C11 1.384(7) . ?
C14 C10 1.400(8) . ?
C12 C11 1.372(8) . ?
C2 H2 0.9300 . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
O1 H2O 0.85(2) . ?
O1 H1O 0.86(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
C6 N1 C12 119.1(5) . . ?
C6 N1 C4 120.6(5) . . ?
C12 N1 C4 120.2(5) . . ?
C8 C7 C13 120.2(6) . . ?
C8 C7 H7 119.9 . . ?
C13 C7 H7 119.9 . . ?
N1 C6 C13 123.3(5) . . ?
N1 C6 H6 118.4 . . ?
C13 C6 H6 118.4 . . ?
C7 C8 C9 122.9(6) . . ?
C7 C8 H8 118.6 . . ?
C9 C8 H8 118.6 . . ?
C3 C4 N1 121.1(6) . . ?
C3 C4 H4 119.5 . . ?
N1 C4 H4 119.5 . . ?
C4 C3 C2 120.2(6) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C6 C13 C7 122.9(5) . . ?
C6 C13 C14 119.3(5) . . ?
C7 C13 C14 117.8(5) . . ?
C2 C1 C12 122.1(6) . . ?
C2 C1 H1 118.9 . . ?
C12 C1 H1 118.9 . . ?
C10 C9 C8 117.8(6) . . ?
C10 C9 C15 121.6(6) . . ?
C8 C9 C15 120.5(6) . . ?
C11 C14 C10 124.9(5) . . ?
C11 C14 C13 116.0(5) . . ?
C10 C14 C13 119.1(5) . . ?
C11 C12 N1 119.2(5) . . ?
C11 C12 C1 124.0(5) . . ?
N1 C12 C1 116.8(5) . . ?
C1 C2 C3 119.5(6) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C9 C10 C14 122.2(5) . . ?
C9 C10 H10 118.9 . . ?
C14 C10 H10 118.9 . . ?
C12 C11 C14 123.2(5) . . ?
C12 C11 H11 118.4 . . ?
C14 C11 H11 118.4 . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H2O O1 H1O 90(10) . . ?







_database_code_depnum_ccdc_archive 'CCDC 975292'
#######################################################################
#
#                 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_9-C(CH3)3_photodimer

_audit_creation_date             2014-08-25T00:34:35-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C34 H36 N2 2+, 2(Br 1-), H2 O'
_chemical_formula_sum            'C34 H38 Br2 N2 O'
_chemical_formula_weight         650.48

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

_cell_length_a                   7.7034(7)
_cell_length_b                   9.1410(10)
_cell_length_c                   12.257(2)
_cell_angle_alpha                88.730(6)
_cell_angle_beta                 78.321(6)
_cell_angle_gamma                71.486(4)
_cell_volume                     800.65(17)
_cell_formula_units_Z            1
_cell_measurement_temperature    298(2)

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             334

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3862
_exptl_absorpt_correction_T_max  0.9507
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_number            4589
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         22.5
_diffrn_reflns_theta_full        22.5
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_reflns_number_total             2055
_reflns_number_gt                1592
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0866P)²+0.4520P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2055
_refine_ls_number_parameters     193
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.1666
_refine_ls_wR_factor_gt          0.1529
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.079

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.23163(10) 0.54899(7) 0.13058(7) 0.0913(4) Uani 1 1 d D . .
N1 N 0.3520(6) 0.8841(5) -0.0412(4) 0.0553(11) Uani 1 1 d . . .
C14 C 0.3234(7) 1.0757(6) 0.1419(4) 0.0529(13) Uani 1 1 d . . .
C13 C 0.4067(7) 0.9155(6) 0.1428(4) 0.0497(13) Uani 1 1 d . . .
C12 C 0.2657(7) 1.0389(6) -0.0428(4) 0.0497(13) Uani 1 1 d . . .
C11 C 0.3171(7) 1.1424(6) 0.0287(4) 0.0511(13) Uani 1 1 d . . .
H11 H 0.2182 1.2427 0.0385 0.061 Uiso 1 1 calc R . .
C10 C 0.2527(8) 1.1607(7) 0.2398(5) 0.0612(15) Uani 1 1 d . . .
H10 H 0.1979 1.2669 0.2379 0.073 Uiso 1 1 calc R . .
C6 C 0.4915(7) 0.8308(6) 0.0305(4) 0.0537(13) Uani 1 1 d . . .
H6 H 0.5153 0.72 0.0406 0.064 Uiso 1 1 calc R . .
C2 C 0.0994(9) 0.9842(9) -0.1740(5) 0.0693(17) Uani 1 1 d . . .
H2 H 0.0127 1.0187 -0.2195 0.083 Uiso 1 1 calc R . .
C9 C 0.2592(9) 1.0943(7) 0.3431(5) 0.0668(16) Uani 1 1 d . . .
C8 C 0.3384(9) 0.9344(8) 0.3432(5) 0.0686(16) Uani 1 1 d U . .
H8 H 0.3428(10) 0.878(4) 0.423(5) 0.082 Uiso 1 1 calc R . .
C4 C 0.3157(8) 0.7805(8) -0.1028(5) 0.0626(16) Uani 1 1 d . . .
H4 H 0.373(5) 0.681(8) -0.0993(6) 0.075 Uiso 1 1 calc R . .
C7 C 0.4121(8) 0.8451(7) 0.2438(5) 0.0633(16) Uani 1 1 d U . .
H7 H 0.4648 0.7385 0.2454 0.076 Uiso 1 1 calc R . .
C1 C 0.1358(8) 1.0901(7) -0.1103(5) 0.0613(15) Uani 1 1 d . . .
H1 H 0.0734 1.1951 -0.1127 0.074 Uiso 1 1 calc R . .
C3 C 0.1892(9) 0.8307(8) -0.1707(5) 0.0701(17) Uani 1 1 d . . .
H3 H 0.166(2) 0.763(6) -0.213(4) 0.084 Uiso 1 1 calc R . .
C17 C 0.3152(14) 1.3003(10) 0.4482(7) 0.106(3) Uani 1 1 d . . .
H17A H 0.4422 1.2346 0.4415 0.159 Uiso 1 1 calc R . .
H17B H 0.2767 1.3622 0.5164 0.159 Uiso 1 1 calc R . .
H17C H 0.3064 1.3664 0.3862 0.159 Uiso 1 1 calc R . .
C15 C 0.1863(12) 1.1997(8) 0.4488(6) 0.086(2) Uani 1 1 d . . .
C18 C 0.1918(16) 1.1065(10) 0.5572(6) 0.115(3) Uani 1 1 d . . .
H18A H 0.1099 1.0454 0.5618 0.173 Uiso 1 1 calc R . .
H18B H 0.1518 1.1769 0.6211 0.173 Uiso 1 1 calc R . .
H18C H 0.3172 1.04 0.5553 0.173 Uiso 1 1 calc R . .
C16 C -0.0163(14) 1.3007(10) 0.4534(7) 0.113(3) Uani 1 1 d . . .
H16A H -0.0204 1.3708 0.3937 0.17 Uiso 1 1 calc R . .
H16B H -0.0648 1.3584 0.5235 0.17 Uiso 1 1 calc R . .
H16C H -0.0907 1.2364 0.4457 0.17 Uiso 1 1 calc R . .
O1 O 0.181(2) 0.4810(19) -0.1242(13) 0.155(6) Uani 0.5 1 d PD . .
H1O H 0.0864(15) 0.4709(19) -0.139(3) 0.232 Uiso 0.5 1 d PD . .
H2O H 0.167(7) 0.4977(17) -0.055(2) 0.232 Uiso 0.5 1 d PD . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C4 1.353(7) . ?
N1 C12 1.361(7) . ?
N1 C6 1.482(7) . ?
C14 C10 1.360(8) . ?
C14 C13 1.401(7) . ?
C14 C11 1.506(7) . ?
C13 C7 1.385(8) . ?
C13 C6 1.512(8) . ?
C12 C1 1.387(8) . ?
C12 C11 1.496(8) . ?
C11 C6 1.597(8) 2_675 ?
C11 H11 0.98 . ?
C10 C9 1.395(8) . ?
C10 H10 0.93 . ?
C6 C11 1.597(8) 2_675 ?
C6 H6 0.98 . ?
C2 C3 1.357(9) . ?
C2 C1 1.386(9) . ?
C2 H2 0.93 . ?
C9 C8 1.393(9) . ?
C9 C15 1.530(10) . ?
C8 C7 1.394(9) . ?
C8 H8 1.099 . ?
C4 C3 1.372(9) . ?
C4 H4 0.8791 . ?
C7 H7 0.93 . ?
C1 H1 0.93 . ?
C3 H3 0.8944 . ?
C17 C15 1.552(11) . ?
C17 H17A 0.96 . ?
C17 H17B 0.96 . ?
C17 H17C 0.96 . ?
C15 C16 1.530(12) . ?
C15 C18 1.563(11) . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C16 H16A 0.96 . ?
C16 H16B 0.96 . ?
C16 H16C 0.96 . ?
O1 H1O 0.819(9) . ?
O1 H2O 0.849(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C12 122.4(5) . . ?
C4 N1 C6 120.2(5) . . ?
C12 N1 C6 117.4(4) . . ?
C10 C14 C13 119.7(5) . . ?
C10 C14 C11 124.1(5) . . ?
C13 C14 C11 116.1(5) . . ?
C7 C13 C14 119.5(5) . . ?
C7 C13 C6 124.1(5) . . ?
C14 C13 C6 116.4(5) . . ?
N1 C12 C1 117.9(5) . . ?
N1 C12 C11 117.7(4) . . ?
C1 C12 C11 124.4(5) . . ?
C12 C11 C14 109.0(4) . . ?
C12 C11 C6 110.8(4) . 2_675 ?
C14 C11 C6 113.1(4) . 2_675 ?
C12 C11 H11 107.9 . . ?
C14 C11 H11 107.9 . . ?
C6 C11 H11 107.9 2_675 . ?
C14 C10 C9 122.4(6) . . ?
C14 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
N1 C6 C13 107.7(4) . . ?
N1 C6 C11 109.8(4) . 2_675 ?
C13 C6 C11 113.4(4) . 2_675 ?
N1 C6 H6 108.6 . . ?
C13 C6 H6 108.6 . . ?
C11 C6 H6 108.6 2_675 . ?
C3 C2 C1 120.6(6) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C8 C9 C10 117.4(6) . . ?
C8 C9 C15 123.8(6) . . ?
C10 C9 C15 118.8(6) . . ?
C9 C8 C7 121.2(6) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
N1 C4 C3 119.9(6) . . ?
N1 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C13 C7 C8 119.8(6) . . ?
C13 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C12 C1 C2 119.8(6) . . ?
C12 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C2 C3 C4 119.4(6) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C9 C15 C16 110.2(6) . . ?
C9 C15 C17 108.3(6) . . ?
C16 C15 C17 111.0(7) . . ?
C9 C15 C18 112.2(6) . . ?
C16 C15 C18 107.9(7) . . ?
C17 C15 C18 107.1(7) . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
H1O O1 H2O 110(3) . . ?


_vrf_THETM01_ALERT_3_A           
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
            Calculated sin(theta_max)/wavelength =    0.5384
RESPONSE: The best-quality dataset was reported. The single crystals
were small in size and diffracted poorly despite the presence of
heavy atoms).
;



_database_code_depnum_ccdc_archive 'CCDC 975293'
#######################################################################
#
#                 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_added_by_encifer


_chemical_name_systematic        ?
_chemical_name_common            '9-tert-butylacridizinium bromide monohydrate'
_chemical_formula_moiety         '(C17 H18  N1 +1) (Br -1) (H2O)'
_chemical_formula_structural     '(C17 H18  N1 +1) (Br -1) (H2O)'
_chemical_formula_analytical     ?
_chemical_formula_sum            'C17 H20 Br1 N1 O1'
_chemical_formula_weight         334.26
_chemical_melting_point          ?
_chemical_compound_source        ?

loop_
_atom_type_symbol
?
_atom_type_description           ?
_atom_type_scat_dispersion_real  ?
_atom_type_scat_dispersion_imag  ?
_atom_type_scat_source           ?
_atom_type_scat_length_neutron   ?


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

# 6. POWDER SPECIMEN AND CRYSTAL DATA

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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


_cell_length_a                   18.08801(59)
_cell_length_b                   12.04679(49)
_cell_length_c                   7.22980(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1575.39(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293
_exptl_crystal_density_diffrn    1.4093
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688

_cell_special_details            ?


_pd_spec_mounting                'borosilicate capillary'
_pd_spec_mount_mode              transmission
_pd_spec_shape                   cylinder
_pd_char_particle_morphology     ?
_pd_char_colour                  yellow
_pd_prep_temperature             293


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

# 7. EXPERIMENTAL DATA

_diffrn_ambient_temperature      293
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              ?
_diffrn_radiation_type           'Cu K\a~1~'
_diffrn_source_voltage           40
_diffrn_source_current           30
_diffrn_measurement_device_type  'Stoe StadiP'
_diffrn_detector                 'Single photon counting'
_diffrn_detector_type            'DECTRIS MYTHEN 1K'
_pd_meas_scan_method             cont
_pd_meas_special_details         ?
_diffrn_radiation_wavelength     1.5406
_diffrn_radiation_monochromator  none
_pd_meas_number_of_points        3861
_pd_meas_2theta_range_min        2.134
_pd_meas_2theta_range_max        59.900
_pd_meas_2theta_range_inc        0.015



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

# 8. REFINEMENT DATA

_pd_proc_ls_profile_function     pseudo-Voigt
_pd_proc_ls_background_function  'Chebyshev polynomial'


_pd_proc_ls_prof_R_factor        0.042
_pd_proc_ls_prof_wR_factor       0.054
_pd_proc_ls_prof_wR_expected     0.021
_refine_ls_R_I_factor            0.021


_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     36
_refine_ls_number_restraints     0
_refine_ls_number_constraints    102

_refine_ls_goodness_of_fit_all   2.552


_pd_proc_2theta_range_min        5
_pd_proc_2theta_range_max        59.940
_pd_proc_2theta_range_inc        0.0334
_pd_proc_wavelength              1.5406
_pd_block_diffractogram_id       ?


_computing_data_collection       'Stoe Win XPOW 3.0.2.7'
_computing_cell_refinement       'DICVOL 06 (Louer et al)'
_computing_structure_solution    'TOPAS Academic (Coelho 2007) '
_computing_structure_refinement  'TOPAS Academic (Coelho 2007)'
_computing_molecular_graphics    ?
_computing_publication_material  ?


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


# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
H1 H 0.90216(37) -0.59920(57) -0.9913(12) 1 5.688(84)
H2 H 0.86803(51) -0.78409(47) -1.1089(13) 1 5.688(84)
H3 H 0.73170(56) -0.83818(37) -1.1340(17) 1 5.688(84)
H4 H 0.63564(44) -0.69575(41) -1.0502(18) 1 5.688(84)
H5 H 0.60518(30) -0.51049(40) -0.9655(16) 1 5.688(84)
H6 H 0.57416(23) -0.31035(41) -0.8906(15) 1 5.688(84)
H7 H 0.75291(33) -0.08147(39) -0.7732(16) 1 5.688(84)
H8 H 0.84544(26) -0.23139(55) -0.8149(16) 1 5.688(84)
H9 H 0.87474(26) -0.42542(55) -0.9020(13) 1 5.688(84)
H10 H 0.50474(30) -0.17954(49) -0.7411(19) 1 5.688(84)
H11 H 0.51393(35) -0.15893(63) -0.9856(18) 1 5.688(84)
H12 H 0.48402(37) -0.04947(58) -0.8411(19) 1 5.688(84)
H13 H 0.66741(45) -0.00384(45) -0.5991(16) 1 5.688(84)
H14 H 0.59181(50) -0.08714(49) -0.5197(15) 1 5.688(84)
H15 H 0.57450(46) 0.04447(41) -0.6250(17) 1 5.688(84)
H16 H 0.61790(57) -0.03780(55) -1.1114(15) 1 5.688(84)
H17 H 0.68243(50) 0.02447(31) -0.9512(18) 1 5.688(84)
H18 H 0.58736(55) 0.07172(45) -0.9606(17) 1 5.688(84)
H19 H 0.99687(78) -0.4798(13) -0.7449(16) 1 5.688(84)
H20 H 0.99607(78) -0.5913(13) -0.6298(16) 1 5.688(84)
C1 C 0.84481(38) -0.62380(44) -1.0117(11) 1 5.688(84)
C2 C 0.82397(47) -0.72670(39) -1.0716(12) 1 5.688(84)
C3 C 0.74784(49) -0.75557(34) -1.0876(14) 1 5.688(84)
C4 C 0.69481(43) -0.67811(33) -1.0439(15) 1 5.688(84)
C5 C 0.71514(34) -0.56915(29) -0.9865(12) 1 5.688(84)
C6 C 0.66296(29) -0.48628(30) -0.9499(12) 1 5.688(84)
C7 C 0.68442(24) -0.37837(27) -0.9004(11) 1 5.688(84)
C8 C 0.63263(23) -0.29057(31) -0.8748(12) 1 5.688(84)
C9 C 0.65639(27) -0.18409(28) -0.8337(12) 1 5.688(84)
C10 C 0.73429(28) -0.16487(34) -0.8091(13) 1 5.688(84)
C11 C 0.78628(25) -0.24708(41) -0.8312(13) 1 5.688(84)
C12 C 0.76261(24) -0.35617(34) -0.8814(10) 1 5.688(84)
C13 C 0.81533(27) -0.44050(42) -0.9151(11) 1 5.688(84)
C14 C 0.60327(33) -0.08557(33) -0.8207(14) 1 5.688(84)
C15 C 0.52214(31) -0.12045(50) -0.8488(17) 1 5.688(84)
C16 C 0.61015(42) -0.02957(39) -0.6287(15) 1 5.688(84)
C17 C 0.62443(49) -0.00059(39) -0.9731(16) 1 5.688(84)
N1 N 0.79228(33) -0.54334(36) -0.96903(99) 1 5.688(84)
O1 O 0.98527(79) -0.5592(13) -0.7515(16) 1 5.688(84)
Br1 Br 0.99863(16) -0.29760(18) -0.84002(92) 1 5.688(84)


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


# 10. MOLECULAR GEOMETRY

_geom_special_details            ?

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
H1 C1 1.09(1)
H2 C2 1.09(1)
H3 C3 1.090(8)
H4 C4 1.09(1)
H5 C6 1.091(8)
H6 C8 1.090(6)
H7 C10 1.091(7)
H8 C11 1.093(7)
H9 C13 1.094(7)
H10 C15 1.10(1)
H11 C15 1.10(2)
H12 C15 1.100(9)
H13 C16 1.10(1)
H14 C16 1.10(1)
H15 C16 1.101(9)
H16 C17 1.10(1)
H17 C17 1.10(1)
H18 C17 1.10(1)
C1 C2 1.366(8)
C1 N1 1.392(8)
C2 C3 1.42(1)
C3 C4 1.38(1)
C4 C5 1.425(7)
C5 C6 1.399(7)
C5 N1 1.435(8)
C6 C7 1.403(6)
C7 C8 1.425(6)
C7 C12 1.446(6)
C8 C9 1.385(6)
C9 C10 1.439(7)
C9 C14 1.530(6)
C10 C11 1.375(7)
C11 C12 1.429(7)
C12 C13 1.414(7)
C13 N1 1.364(7)
C14 C15 1.540(8)
C14 C16 1.55(1)
C14 C17 1.55(1)
H19 O1 0.98(2)
H20 O1 0.98(2)



loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
H1 C1 C2 123.6(7)
H1 C1 N1 115.5(7)
C2 C1 N1 120.9(6)
H2 C2 C1 116.9(8)
H2 C2 C3 122.2(8)
C1 C2 C3 120.9(7)
H3 C3 C2 120.4(8)
H3 C3 C4 120.2(8)
C2 C3 C4 119.3(7)
H4 C4 C3 122.8(8)
H4 C4 C5 116.4(8)
C3 C4 C5 120.8(7)
C4 C5 C6 122.6(6)
C4 C5 N1 118.4(6)
C6 C5 N1 119.0(5)
H5 C6 C5 115.8(7)
H5 C6 C7 122.6(6)
C5 C6 C7 121.5(5)
C6 C7 C8 122.6(5)
C6 C7 C12 117.8(5)
C8 C7 C12 119.6(5)
H6 C8 C7 117.5(6)
H6 C8 C9 121.7(6)
C7 C8 C9 120.8(5)
C8 C9 C10 118.6(5)
C8 C9 C14 122.5(5)
C10 C9 C14 118.9(5)
H7 C10 C9 118.7(7)
H7 C10 C11 118.7(7)
C9 C10 C11 122.6(6)
H8 C11 C10 122.2(7)
H8 C11 C12 118.7(7)
C10 C11 C12 119.1(6)
C7 C12 C11 119.2(5)
C7 C12 C13 120.7(5)
C11 C12 C13 120.1(5)
H9 C13 C12 121.9(6)
H9 C13 N1 118.4(7)
C12 C13 N1 119.7(5)
C9 C14 C15 112.3(6)
C9 C14 C16 110.0(5)
C9 C14 C17 108.3(6)
C15 C14 C16 108.3(6)
C15 C14 C17 108.7(6)
C16 C14 C17 109.2(6)
H10 C15 H11 108.9(9)
H10 C15 H12 106.7(9)
H10 C15 C14 110.8(8)
H11 C15 H12 106.7(9)
H11 C15 C14 111.2(8)
H12 C15 C14 112.2(8)
H13 C16 H14 108.7(9)
H13 C16 H15 108.5(9)
H13 C16 C14 111.8(8)
H14 C16 H15 108.5(9)
H14 C16 C14 110.1(8)
H15 C16 C14 109.1(8)
H16 C17 H17 110(1)
H16 C17 H18 109(1)
H16 C17 C14 110.4(8)
H17 C17 H18 111(1)
H17 C17 C14 108.3(8)
H18 C17 C14 108.2(8)
C1 N1 C5 119.6(5)
C1 N1 C13 119.2(6)
C5 N1 C13 121.3(5)
H19 O1 H20 107(2)



_database_code_depnum_ccdc_archive 'CCDC 992871'
