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

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'C Aakeroy'
_publ_contact_author_email       AAKEROY@KSU.EDU

_publ_section_title              
;
Cyanoximes as effective and selective co-crystallizing
agents
;
loop_
_publ_author_name
'C Aakeroy'
'John Desper'
'Debra J Salmon'
'Michelle M Smith'

# Attachment 'xray.cif.cif'

data_A1
_database_code_depnum_ccdc_archive 'CCDC 694148'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(4-bromo-PhC(CN)(=NOH)), 3-bromo-5-methoxypyridine
;
_chemical_name_common            
'(4-bromo-PhC(CN)(=NOH)), 3-bromo-5-methoxypyridine'
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C8 H5 Br N2 O) (C6 H6 Br N O)
;
_chemical_formula_sum            'C14 H11 Br2 N3 O2'
_chemical_formula_weight         413.08

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.9907(6)
_cell_length_b                   8.0552(7)
_cell_length_c                   15.3027(13)
_cell_angle_alpha                79.305(5)
_cell_angle_beta                 89.038(5)
_cell_angle_gamma                64.660(5)
_cell_volume                     763.37(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2866
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      27.85

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    5.316
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.225
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5513
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_sigmaI/netI    0.0723
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.36
_diffrn_reflns_theta_max         27.88
_reflns_number_total             3350
_reflns_number_gt                2663
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3350
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1704
_refine_ls_wR_factor_gt          0.1633
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.128
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.05763(9) 0.83758(7) -0.12842(4) 0.0358(2) Uani 1 1 d . . .
Br2 Br 0.97220(8) 0.16580(7) 0.65616(4) 0.0388(2) Uani 1 1 d . . .
C11 C 0.3337(8) 0.3529(7) 0.1193(3) 0.0268(10) Uani 1 1 d . . .
C12 C 0.2131(9) 0.5349(7) 0.1292(4) 0.0344(11) Uani 1 1 d . . .
H12 H 0.1874 0.5611 0.1874 0.041 Uiso 1 1 calc R . .
C13 C 0.1297(9) 0.6787(7) 0.0567(4) 0.0375(12) Uani 1 1 d . . .
H13 H 0.0478 0.8035 0.0647 0.045 Uiso 1 1 calc R . .
C14 C 0.1656(8) 0.6407(7) -0.0272(3) 0.0302(10) Uani 1 1 d . . .
C15 C 0.2846(8) 0.4590(7) -0.0405(4) 0.0331(11) Uani 1 1 d . . .
H15 H 0.3081 0.4340 -0.0990 0.040 Uiso 1 1 calc R . .
C16 C 0.3683(8) 0.3150(7) 0.0339(3) 0.0292(10) Uani 1 1 d . . .
H16 H 0.4497 0.1900 0.0263 0.035 Uiso 1 1 calc R . .
N17 N 0.4219(7) 0.2355(6) 0.2753(3) 0.0299(9) Uani 1 1 d . . .
O17 O 0.5096(6) 0.0768(5) 0.3392(3) 0.0323(8) Uani 1 1 d . . .
H17 H 0.468(8) 0.150(7) 0.391(4) 0.039 Uiso 1 1 d . . .
C17 C 0.4264(7) 0.1979(6) 0.1965(3) 0.0265(10) Uani 1 1 d . . .
N18 N 0.5938(10) -0.1440(7) 0.1746(4) 0.0529(14) Uani 1 1 d . . .
C18 C 0.5165(9) 0.0079(7) 0.1850(4) 0.0350(12) Uani 1 1 d . . .
N21 N 0.5011(7) 0.2106(6) 0.4868(3) 0.0301(9) Uani 1 1 d . . .
C22 C 0.6884(8) 0.1593(7) 0.5295(3) 0.0302(10) Uani 1 1 d . . .
H22 H 0.8130 0.0680 0.5109 0.036 Uiso 1 1 calc R . .
C23 C 0.7028(8) 0.2371(7) 0.6000(3) 0.0273(10) Uani 1 1 d . . .
C24 C 0.5236(7) 0.3694(6) 0.6302(3) 0.0254(9) Uani 1 1 d . . .
H24 H 0.5331 0.4229 0.6793 0.030 Uiso 1 1 calc R . .
O25 O 0.1405(5) 0.5481(5) 0.6032(3) 0.0352(8) Uani 1 1 d . . .
C25 C 0.3314(8) 0.4190(7) 0.5852(3) 0.0284(10) Uani 1 1 d . . .
C26 C 0.3280(8) 0.3364(7) 0.5137(3) 0.0294(10) Uani 1 1 d . . .
H26 H 0.1956 0.3718 0.4827 0.035 Uiso 1 1 calc R . .
C27 C 0.1339(8) 0.6196(8) 0.6787(4) 0.0382(12) Uani 1 1 d . . .
H27A H -0.0116 0.7102 0.6844 0.057 Uiso 1 1 calc R . .
H27B H 0.2280 0.6822 0.6743 0.057 Uiso 1 1 calc R . .
H27C H 0.1807 0.5175 0.7311 0.057 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C14 1.894(5) . ?
Br2 C23 1.887(5) . ?
C11 C12 1.380(7) . ?
C11 C16 1.391(7) . ?
C11 C17 1.470(7) . ?
C12 C13 1.370(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.370(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(7) . ?
C15 C16 1.391(7) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
N17 C17 1.293(6) . ?
N17 O17 1.361(5) . ?
O17 H17 1.03(5) . ?
C17 C18 1.429(6) . ?
N18 C18 1.148(7) . ?
N21 C26 1.322(7) . ?
N21 C22 1.333(6) . ?
C22 C23 1.368(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.392(7) . ?
C24 C25 1.381(7) . ?
C24 H24 0.9500 . ?
O25 C25 1.358(6) . ?
O25 C27 1.375(7) . ?
C25 C26 1.388(7) . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C11 C16 119.0(5) . . ?
C12 C11 C17 121.8(5) . . ?
C16 C11 C17 119.1(4) . . ?
C13 C12 C11 121.4(5) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C12 119.3(5) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 121.4(5) . . ?
C13 C14 Br1 120.2(4) . . ?
C15 C14 Br1 118.4(4) . . ?
C16 C15 C14 118.4(5) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
C11 C16 C15 120.5(5) . . ?
C11 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C17 N17 O17 111.7(4) . . ?
N17 O17 H17 93(3) . . ?
N17 C17 C18 120.3(5) . . ?
N17 C17 C11 119.2(4) . . ?
C18 C17 C11 120.5(4) . . ?
N18 C18 C17 178.0(6) . . ?
C26 N21 C22 119.4(4) . . ?
N21 C22 C23 120.6(5) . . ?
N21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C24 121.5(4) . . ?
C22 C23 Br2 119.1(4) . . ?
C24 C23 Br2 119.4(4) . . ?
C25 C24 C23 116.8(5) . . ?
C25 C24 H24 121.6 . . ?
C23 C24 H24 121.6 . . ?
C25 O25 C27 117.3(4) . . ?
O25 C25 C24 125.6(5) . . ?
O25 C25 C26 115.6(5) . . ?
C24 C25 C26 118.9(5) . . ?
N21 C26 C25 122.9(5) . . ?
N21 C26 H26 118.6 . . ?
C25 C26 H26 118.6 . . ?
O25 C27 H27A 109.5 . . ?
O25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 C11 C12 C13 -0.9(7) . . . . ?
C17 C11 C12 C13 179.1(4) . . . . ?
C11 C12 C13 C14 0.4(8) . . . . ?
C12 C13 C14 C15 0.2(7) . . . . ?
C12 C13 C14 Br1 -178.6(4) . . . . ?
C13 C14 C15 C16 -0.3(7) . . . . ?
Br1 C14 C15 C16 178.5(3) . . . . ?
C12 C11 C16 C15 0.7(7) . . . . ?
C17 C11 C16 C15 -179.3(4) . . . . ?
C14 C15 C16 C11 -0.2(7) . . . . ?
O17 N17 C17 C18 -0.1(6) . . . . ?
O17 N17 C17 C11 178.6(4) . . . . ?
C12 C11 C17 N17 -10.3(7) . . . . ?
C16 C11 C17 N17 169.7(4) . . . . ?
C12 C11 C17 C18 168.4(5) . . . . ?
C16 C11 C17 C18 -11.6(7) . . . . ?
C26 N21 C22 C23 -0.7(7) . . . . ?
N21 C22 C23 C24 0.9(7) . . . . ?
N21 C22 C23 Br2 -178.1(3) . . . . ?
C22 C23 C24 C25 -0.4(7) . . . . ?
Br2 C23 C24 C25 178.6(3) . . . . ?
C27 O25 C25 C24 -8.0(7) . . . . ?
C27 O25 C25 C26 173.8(4) . . . . ?
C23 C24 C25 O25 -178.4(4) . . . . ?
C23 C24 C25 C26 -0.3(7) . . . . ?
C22 N21 C26 C25 -0.1(7) . . . . ?
O25 C25 C26 N21 178.8(4) . . . . ?
C24 C25 C26 N21 0.5(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O17 H17 N21 1.03(5) 1.69(5) 2.667(6) 157(5) .

_diffrn_measured_fraction_theta_max 0.917
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.735
_refine_diff_density_min         -1.056
_refine_diff_density_rms         0.201

#END

data_A2
_database_code_depnum_ccdc_archive 'CCDC 694149'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(4-bromo-PhC(CN)(=NOH)), 1-(4-bromobenzyl)-2-methylbenzimidazole
;
_chemical_name_common            
;(4-bromo-PhC(CN)(=NOH)), 1-(4-bromobenzyl)-2-
methylbenzimidazole
;
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C8 H5 Br N2 O) (C15 H13 Br N2)
;
_chemical_formula_sum            'C23 H18 Br2 N4 O'
_chemical_formula_weight         526.23

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   4.9374(6)
_cell_length_b                   22.597(3)
_cell_length_c                   19.233(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.869(2)
_cell_angle_gamma                90.00
_cell_volume                     2130.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6131
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      29.25

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1048
_exptl_absorpt_coefficient_mu    3.828
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.656
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24200
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         30.02
_reflns_number_total             6170
_reflns_number_gt                4792
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0500P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6170
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0825
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.79725(4) 0.584899(9) 0.108998(11) 0.02328(7) Uani 1 1 d . . .
Br2 Br 0.98977(5) 0.082854(10) 0.607905(12) 0.03154(7) Uani 1 1 d . . .
N11 N 1.0656(3) 0.33215(7) 0.40216(8) 0.0177(3) Uani 1 1 d . . .
C12 C 0.9769(4) 0.38499(8) 0.42489(10) 0.0183(4) Uani 1 1 d . . .
N13 N 0.7625(3) 0.40511(7) 0.38408(9) 0.0199(3) Uani 1 1 d . . .
C14 C 0.7083(4) 0.36362(9) 0.33081(10) 0.0191(4) Uani 1 1 d . . .
C15 C 0.5066(4) 0.36263(9) 0.27378(11) 0.0239(4) Uani 1 1 d . . .
H15 H 0.3788 0.3940 0.2656 0.029 Uiso 1 1 calc R . .
C16 C 0.4987(4) 0.31447(10) 0.22953(11) 0.0266(5) Uani 1 1 d . . .
H16 H 0.3628 0.3128 0.1902 0.032 Uiso 1 1 calc R . .
C17 C 0.6869(5) 0.26781(10) 0.24132(11) 0.0259(4) Uani 1 1 d . . .
H17 H 0.6761 0.2354 0.2096 0.031 Uiso 1 1 calc R . .
C18 C 0.8886(4) 0.26806(9) 0.29829(10) 0.0220(4) Uani 1 1 d . . .
H18 H 1.0149 0.2364 0.3069 0.026 Uiso 1 1 calc R . .
C19 C 0.8952(4) 0.31692(8) 0.34186(10) 0.0179(4) Uani 1 1 d . . .
C20 C 1.1097(4) 0.41633(9) 0.48765(11) 0.0229(4) Uani 1 1 d . . .
H20A H 0.9870 0.4471 0.5015 0.034 Uiso 1 1 calc R . .
H20B H 1.2797 0.4346 0.4767 0.034 Uiso 1 1 calc R . .
H20C H 1.1501 0.3880 0.5261 0.034 Uiso 1 1 calc R . .
C21 C 1.0839(4) 0.14893(9) 0.55455(10) 0.0216(4) Uani 1 1 d . . .
C22 C 1.2784(4) 0.14221(9) 0.50941(11) 0.0220(4) Uani 1 1 d . . .
H22 H 1.3683 0.1054 0.5057 0.026 Uiso 1 1 calc R . .
C23 C 1.3403(4) 0.19036(9) 0.46940(10) 0.0200(4) Uani 1 1 d . . .
H23 H 1.4719 0.1862 0.4375 0.024 Uiso 1 1 calc R . .
C24 C 1.2130(4) 0.24451(8) 0.47521(10) 0.0166(4) Uani 1 1 d . . .
C25 C 1.0188(4) 0.25003(9) 0.52163(10) 0.0205(4) Uani 1 1 d . . .
H25 H 0.9306 0.2870 0.5260 0.025 Uiso 1 1 calc R . .
C26 C 0.9526(4) 0.20231(9) 0.56154(10) 0.0216(4) Uani 1 1 d . . .
H26 H 0.8197 0.2062 0.5931 0.026 Uiso 1 1 calc R . .
C27 C 1.2963(4) 0.29677(8) 0.43392(10) 0.0184(4) Uani 1 1 d . . .
H27A H 1.4190 0.3224 0.4653 0.022 Uiso 1 1 calc R . .
H27B H 1.4006 0.2823 0.3965 0.022 Uiso 1 1 calc R . .
C31 C -0.0566(4) 0.56230(9) 0.28222(10) 0.0173(4) Uani 1 1 d . . .
C32 C -0.1707(4) 0.51289(9) 0.24598(10) 0.0188(4) Uani 1 1 d . . .
H32 H -0.0957 0.4747 0.2564 0.023 Uiso 1 1 calc R . .
C33 C -0.3923(4) 0.51911(9) 0.19497(10) 0.0200(4) Uani 1 1 d . . .
H33 H -0.4700 0.4855 0.1706 0.024 Uiso 1 1 calc R . .
C34 C -0.4988(4) 0.57502(9) 0.18006(10) 0.0201(4) Uani 1 1 d . . .
C35 C -0.3942(4) 0.62431(9) 0.21586(11) 0.0217(4) Uani 1 1 d . . .
H35 H -0.4722 0.6622 0.2056 0.026 Uiso 1 1 calc R . .
C36 C -0.1725(4) 0.61785(9) 0.26735(10) 0.0204(4) Uani 1 1 d . . .
H36 H -0.0996 0.6516 0.2925 0.025 Uiso 1 1 calc R . .
C37 C 0.1841(4) 0.55582(8) 0.33487(10) 0.0171(4) Uani 1 1 d . . .
N37 N 0.3056(3) 0.50563(7) 0.34499(9) 0.0200(3) Uani 1 1 d . . .
O37 O 0.5254(3) 0.50814(6) 0.39558(7) 0.0222(3) Uani 1 1 d . . .
H37 H 0.605(5) 0.4708(11) 0.3903(12) 0.027 Uiso 1 1 d . . .
C38 C 0.2888(4) 0.60833(9) 0.37292(10) 0.0202(4) Uani 1 1 d . . .
N38 N 0.3689(4) 0.65001(8) 0.40247(10) 0.0276(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C34 1.899(2) . ?
Br2 C21 1.901(2) . ?
N11 C12 1.362(2) . ?
N11 C19 1.392(2) . ?
N11 C27 1.464(2) . ?
C12 N13 1.321(2) . ?
C12 C20 1.483(3) . ?
N13 C14 1.391(3) . ?
C14 C15 1.391(3) . ?
C14 C19 1.401(3) . ?
C15 C16 1.379(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.406(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(3) . ?
C18 H18 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.378(3) . ?
C21 C26 1.384(3) . ?
C22 C23 1.388(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.386(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.391(3) . ?
C24 C27 1.508(3) . ?
C25 C26 1.385(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C31 C36 1.395(3) . ?
C31 C32 1.399(3) . ?
C31 C37 1.474(3) . ?
C32 C33 1.387(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.385(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.377(3) . ?
C35 C36 1.393(3) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 N37 1.287(2) . ?
C37 C38 1.456(3) . ?
N37 O37 1.369(2) . ?
O37 H37 0.94(2) . ?
C38 N38 1.146(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N11 C19 107.37(16) . . ?
C12 N11 C27 127.52(17) . . ?
C19 N11 C27 125.10(16) . . ?
N13 C12 N11 112.14(17) . . ?
N13 C12 C20 124.35(18) . . ?
N11 C12 C20 123.51(18) . . ?
C12 N13 C14 106.01(16) . . ?
C15 C14 N13 130.43(19) . . ?
C15 C14 C19 120.25(19) . . ?
N13 C14 C19 109.31(17) . . ?
C16 C15 C14 117.7(2) . . ?
C16 C15 H15 121.2 . . ?
C14 C15 H15 121.2 . . ?
C15 C16 C17 121.52(19) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C18 C17 C16 121.44(19) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C19 C18 C17 116.33(19) . . ?
C19 C18 H18 121.8 . . ?
C17 C18 H18 121.8 . . ?
C18 C19 N11 132.05(18) . . ?
C18 C19 C14 122.79(18) . . ?
N11 C19 C14 105.16(17) . . ?
C12 C20 H20A 109.5 . . ?
C12 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C12 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C26 121.81(18) . . ?
C22 C21 Br2 119.19(15) . . ?
C26 C21 Br2 119.00(15) . . ?
C21 C22 C23 118.65(18) . . ?
C21 C22 H22 120.7 . . ?
C23 C22 H22 120.7 . . ?
C24 C23 C22 121.02(18) . . ?
C24 C23 H23 119.5 . . ?
C22 C23 H23 119.5 . . ?
C23 C24 C25 119.00(17) . . ?
C23 C24 C27 119.60(17) . . ?
C25 C24 C27 121.34(17) . . ?
C26 C25 C24 120.79(18) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C21 C26 C25 118.72(18) . . ?
C21 C26 H26 120.6 . . ?
C25 C26 H26 120.6 . . ?
N11 C27 C24 113.56(15) . . ?
N11 C27 H27A 108.9 . . ?
C24 C27 H27A 108.9 . . ?
N11 C27 H27B 108.9 . . ?
C24 C27 H27B 108.9 . . ?
H27A C27 H27B 107.7 . . ?
C36 C31 C32 119.03(18) . . ?
C36 C31 C37 120.51(18) . . ?
C32 C31 C37 120.45(17) . . ?
C33 C32 C31 120.56(18) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C34 C33 C32 119.14(19) . . ?
C34 C33 H33 120.4 . . ?
C32 C33 H33 120.4 . . ?
C35 C34 C33 121.58(19) . . ?
C35 C34 Br1 118.48(15) . . ?
C33 C34 Br1 119.93(15) . . ?
C34 C35 C36 119.10(18) . . ?
C34 C35 H35 120.5 . . ?
C36 C35 H35 120.5 . . ?
C35 C36 C31 120.55(19) . . ?
C35 C36 H36 119.7 . . ?
C31 C36 H36 119.7 . . ?
N37 C37 C38 120.75(18) . . ?
N37 C37 C31 120.96(17) . . ?
C38 C37 C31 118.22(17) . . ?
C37 N37 O37 112.73(16) . . ?
N37 O37 H37 101.1(14) . . ?
N38 C38 C37 179.2(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C19 N11 C12 N13 0.0(2) . . . . ?
C27 N11 C12 N13 -179.97(17) . . . . ?
C19 N11 C12 C20 -179.11(18) . . . . ?
C27 N11 C12 C20 0.9(3) . . . . ?
N11 C12 N13 C14 -0.8(2) . . . . ?
C20 C12 N13 C14 178.36(18) . . . . ?
C12 N13 C14 C15 -179.8(2) . . . . ?
C12 N13 C14 C19 1.2(2) . . . . ?
N13 C14 C15 C16 -178.7(2) . . . . ?
C19 C14 C15 C16 0.2(3) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C16 C17 C18 C19 -0.8(3) . . . . ?
C17 C18 C19 N11 -179.54(19) . . . . ?
C17 C18 C19 C14 1.0(3) . . . . ?
C12 N11 C19 C18 -178.8(2) . . . . ?
C27 N11 C19 C18 1.2(3) . . . . ?
C12 N11 C19 C14 0.7(2) . . . . ?
C27 N11 C19 C14 -179.29(16) . . . . ?
C15 C14 C19 C18 -0.7(3) . . . . ?
N13 C14 C19 C18 178.38(18) . . . . ?
C15 C14 C19 N11 179.72(17) . . . . ?
N13 C14 C19 N11 -1.2(2) . . . . ?
C26 C21 C22 C23 -0.9(3) . . . . ?
Br2 C21 C22 C23 178.35(15) . . . . ?
C21 C22 C23 C24 1.0(3) . . . . ?
C22 C23 C24 C25 -0.5(3) . . . . ?
C22 C23 C24 C27 176.61(18) . . . . ?
C23 C24 C25 C26 -0.1(3) . . . . ?
C27 C24 C25 C26 -177.14(18) . . . . ?
C22 C21 C26 C25 0.3(3) . . . . ?
Br2 C21 C26 C25 -178.91(15) . . . . ?
C24 C25 C26 C21 0.2(3) . . . . ?
C12 N11 C27 C24 102.4(2) . . . . ?
C19 N11 C27 C24 -77.6(2) . . . . ?
C23 C24 C27 N11 137.61(18) . . . . ?
C25 C24 C27 N11 -45.3(3) . . . . ?
C36 C31 C32 C33 1.3(3) . . . . ?
C37 C31 C32 C33 -178.12(17) . . . . ?
C31 C32 C33 C34 0.3(3) . . . . ?
C32 C33 C34 C35 -1.6(3) . . . . ?
C32 C33 C34 Br1 178.63(14) . . . . ?
C33 C34 C35 C36 1.3(3) . . . . ?
Br1 C34 C35 C36 -178.97(15) . . . . ?
C34 C35 C36 C31 0.4(3) . . . . ?
C32 C31 C36 C35 -1.7(3) . . . . ?
C37 C31 C36 C35 177.77(18) . . . . ?
C36 C31 C37 N37 -174.42(18) . . . . ?
C32 C31 C37 N37 5.0(3) . . . . ?
C36 C31 C37 C38 2.8(3) . . . . ?
C32 C31 C37 C38 -177.78(17) . . . . ?
C38 C37 N37 O37 2.6(2) . . . . ?
C31 C37 N37 O37 179.70(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O37 H37 N13 0.94(2) 1.69(3) 2.627(2) 177(2) .

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        30.02
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.678
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.092

#END

data_A3
_database_code_depnum_ccdc_archive 'CCDC 694150'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
(4-bromo-PhC(CN)(=NOH)), 1-(4-bromobenzyl)benzimidazole
;
_chemical_name_common            
'(4-bromo-PhC(CN)(=NOH)), 1-(4-bromobenzyl)benzimidazole'
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C8 H5 Br N2 O) (C14 H11 Br N2)
;
_chemical_formula_sum            'C22 H16 Br2 N4 O'
_chemical_formula_weight         512.21

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   5.3033(6)
_cell_length_b                   13.2294(15)
_cell_length_c                   15.0601(17)
_cell_angle_alpha                102.536(2)
_cell_angle_beta                 99.505(2)
_cell_angle_gamma                94.752(2)
_cell_volume                     1009.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6500
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      30.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508
_exptl_absorpt_coefficient_mu    4.036
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.519
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11582
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         30.05
_reflns_number_total             5763
_reflns_number_gt                4972
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0450P)²+0.0800P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5763
_refine_ls_number_parameters     265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0736
_refine_ls_wR_factor_gt          0.0711
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.23446(3) 0.130843(14) -0.100585(11) 0.02864(6) Uani 1 1 d . . .
Br2 Br -0.26182(3) 0.594556(12) 0.943098(11) 0.02674(6) Uani 1 1 d . . .
N11 N 0.7222(2) 0.20505(10) 0.36245(9) 0.0205(2) Uani 1 1 d . . .
C12 C 0.6814(3) 0.15263(13) 0.42790(10) 0.0227(3) Uani 1 1 d . . .
H12 H 0.7577 0.0916 0.4349 0.027 Uiso 1 1 calc R . .
N13 N 0.5251(3) 0.19506(11) 0.48079(9) 0.0231(3) Uani 1 1 d . . .
C14 C 0.4559(3) 0.28111(12) 0.44730(10) 0.0200(3) Uani 1 1 d . . .
C15 C 0.2866(3) 0.35243(13) 0.47458(11) 0.0229(3) Uani 1 1 d . . .
H15 H 0.1998 0.3481 0.5242 0.028 Uiso 1 1 calc R . .
C16 C 0.2509(3) 0.42954(13) 0.42628(11) 0.0247(3) Uani 1 1 d . . .
H16 H 0.1358 0.4786 0.4429 0.030 Uiso 1 1 calc R . .
C17 C 0.3800(3) 0.43723(13) 0.35342(11) 0.0240(3) Uani 1 1 d . . .
H17 H 0.3528 0.4921 0.3228 0.029 Uiso 1 1 calc R . .
C18 C 0.5459(3) 0.36667(13) 0.32523(11) 0.0224(3) Uani 1 1 d . . .
H18 H 0.6328 0.3714 0.2756 0.027 Uiso 1 1 calc R . .
C19 C 0.5790(3) 0.28848(12) 0.37322(10) 0.0193(3) Uani 1 1 d . . .
C21 C 0.4374(3) 0.14174(12) 0.01856(10) 0.0212(3) Uani 1 1 d . . .
C22 C 0.6791(3) 0.19932(12) 0.04224(11) 0.0224(3) Uani 1 1 d . . .
H22 H 0.7472 0.2308 -0.0012 0.027 Uiso 1 1 calc R . .
C23 C 0.8194(3) 0.20998(12) 0.13078(11) 0.0210(3) Uani 1 1 d . . .
H23 H 0.9853 0.2494 0.1481 0.025 Uiso 1 1 calc R . .
C24 C 0.7209(3) 0.16379(12) 0.19472(10) 0.0193(3) Uani 1 1 d . . .
C25 C 0.4796(3) 0.10480(12) 0.16856(11) 0.0218(3) Uani 1 1 d . . .
H25 H 0.4125 0.0719 0.2113 0.026 Uiso 1 1 calc R . .
C26 C 0.3359(3) 0.09369(12) 0.08019(11) 0.0222(3) Uani 1 1 d . . .
H26 H 0.1707 0.0538 0.0624 0.027 Uiso 1 1 calc R . .
C27 C 0.8775(3) 0.17743(13) 0.29080(11) 0.0230(3) Uani 1 1 d . . .
H27A H 0.9492 0.1117 0.2959 0.028 Uiso 1 1 calc R . .
H27B H 1.0235 0.2329 0.3010 0.028 Uiso 1 1 calc R . .
C31 C -0.0552(3) 0.30103(12) 0.74697(10) 0.0204(3) Uani 1 1 d . . .
C32 C 0.0847(3) 0.39889(13) 0.75905(11) 0.0229(3) Uani 1 1 d . . .
H32 H 0.2204 0.4060 0.7260 0.027 Uiso 1 1 calc R . .
C33 C 0.0273(3) 0.48555(13) 0.81884(11) 0.0232(3) Uani 1 1 d . . .
H33 H 0.1239 0.5519 0.8275 0.028 Uiso 1 1 calc R . .
C34 C -0.1741(3) 0.47412(12) 0.86604(10) 0.0214(3) Uani 1 1 d . . .
C35 C -0.3143(3) 0.37825(13) 0.85578(11) 0.0230(3) Uani 1 1 d . . .
H35 H -0.4499 0.3715 0.8890 0.028 Uiso 1 1 calc R . .
C36 C -0.2540(3) 0.29203(13) 0.79621(11) 0.0226(3) Uani 1 1 d . . .
H36 H -0.3493 0.2257 0.7887 0.027 Uiso 1 1 calc R . .
C37 C 0.0083(3) 0.20877(12) 0.68401(10) 0.0209(3) Uani 1 1 d . . .
N37 N 0.1827(3) 0.21829(11) 0.63470(9) 0.0234(3) Uani 1 1 d . . .
O37 O 0.2217(2) 0.12539(9) 0.58132(8) 0.0265(2) Uani 1 1 d . . .
H37 H 0.343(4) 0.1444(17) 0.5500(15) 0.032 Uiso 1 1 d . . .
C38 C -0.1244(3) 0.10712(13) 0.67962(11) 0.0244(3) Uani 1 1 d . . .
N38 N -0.2271(3) 0.02743(12) 0.67896(11) 0.0321(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C21 1.9035(15) . ?
Br2 C34 1.8973(15) . ?
N11 C12 1.357(2) . ?
N11 C19 1.3867(19) . ?
N11 C27 1.4656(18) . ?
C12 N13 1.318(2) . ?
C12 H12 0.9500 . ?
N13 C14 1.394(2) . ?
C14 C19 1.399(2) . ?
C14 C15 1.400(2) . ?
C15 C16 1.384(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.403(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.391(2) . ?
C18 H18 0.9500 . ?
C21 C22 1.386(2) . ?
C21 C26 1.386(2) . ?
C22 C23 1.387(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.394(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.392(2) . ?
C24 C27 1.510(2) . ?
C25 C26 1.391(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C31 C36 1.397(2) . ?
C31 C32 1.398(2) . ?
C31 C37 1.474(2) . ?
C32 C33 1.385(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.393(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.381(2) . ?
C35 C36 1.385(2) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 N37 1.2923(19) . ?
C37 C38 1.448(2) . ?
N37 O37 1.3666(18) . ?
O37 H37 0.91(2) . ?
C38 N38 1.143(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
C12 N11 C19 106.91(12) . . ?
C12 N11 C27 127.27(13) . . ?
C19 N11 C27 125.76(13) . . ?
N13 C12 N11 113.06(14) . . ?
N13 C12 H12 123.5 . . ?
N11 C12 H12 123.5 . . ?
C12 N13 C14 105.17(13) . . ?
N13 C14 C19 109.42(13) . . ?
N13 C14 C15 130.30(14) . . ?
C19 C14 C15 120.25(14) . . ?
C16 C15 C14 117.28(14) . . ?
C16 C15 H15 121.4 . . ?
C14 C15 H15 121.4 . . ?
C15 C16 C17 121.80(14) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C18 C17 C16 121.49(15) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 116.56(14) . . ?
C17 C18 H18 121.7 . . ?
C19 C18 H18 121.7 . . ?
N11 C19 C18 131.95(14) . . ?
N11 C19 C14 105.44(13) . . ?
C18 C19 C14 122.61(14) . . ?
C22 C21 C26 121.78(14) . . ?
C22 C21 Br1 119.42(12) . . ?
C26 C21 Br1 118.79(12) . . ?
C21 C22 C23 118.50(14) . . ?
C21 C22 H22 120.7 . . ?
C23 C22 H22 120.7 . . ?
C22 C23 C24 121.04(14) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C25 C24 C23 119.26(14) . . ?
C25 C24 C27 120.93(14) . . ?
C23 C24 C27 119.81(14) . . ?
C26 C25 C24 120.43(14) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C21 C26 C25 118.97(14) . . ?
C21 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?
N11 C27 C24 111.82(12) . . ?
N11 C27 H27A 109.3 . . ?
C24 C27 H27A 109.3 . . ?
N11 C27 H27B 109.3 . . ?
C24 C27 H27B 109.3 . . ?
H27A C27 H27B 107.9 . . ?
C36 C31 C32 118.92(14) . . ?
C36 C31 C37 120.68(14) . . ?
C32 C31 C37 120.39(13) . . ?
C33 C32 C31 120.56(14) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C32 C33 C34 119.06(15) . . ?
C32 C33 H33 120.5 . . ?
C34 C33 H33 120.5 . . ?
C35 C34 C33 121.53(14) . . ?
C35 C34 Br2 119.78(11) . . ?
C33 C34 Br2 118.66(12) . . ?
C34 C35 C36 118.86(14) . . ?
C34 C35 H35 120.6 . . ?
C36 C35 H35 120.6 . . ?
C35 C36 C31 121.06(15) . . ?
C35 C36 H36 119.5 . . ?
C31 C36 H36 119.5 . . ?
N37 C37 C38 120.57(14) . . ?
N37 C37 C31 120.51(14) . . ?
C38 C37 C31 118.91(13) . . ?
C37 N37 O37 113.26(13) . . ?
N37 O37 H37 103.2(14) . . ?
N38 C38 C37 177.96(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C19 N11 C12 N13 -0.37(18) . . . . ?
C27 N11 C12 N13 -177.81(14) . . . . ?
N11 C12 N13 C14 0.57(18) . . . . ?
C12 N13 C14 C19 -0.55(16) . . . . ?
C12 N13 C14 C15 177.26(16) . . . . ?
N13 C14 C15 C16 -178.37(15) . . . . ?
C19 C14 C15 C16 -0.8(2) . . . . ?
C14 C15 C16 C17 -0.6(2) . . . . ?
C15 C16 C17 C18 1.2(2) . . . . ?
C16 C17 C18 C19 -0.4(2) . . . . ?
C12 N11 C19 C18 -179.23(16) . . . . ?
C27 N11 C19 C18 -1.7(3) . . . . ?
C12 N11 C19 C14 0.00(16) . . . . ?
C27 N11 C19 C14 177.49(14) . . . . ?
C17 C18 C19 N11 178.16(15) . . . . ?
C17 C18 C19 C14 -1.0(2) . . . . ?
N13 C14 C19 N11 0.34(16) . . . . ?
C15 C14 C19 N11 -177.73(13) . . . . ?
N13 C14 C19 C18 179.66(14) . . . . ?
C15 C14 C19 C18 1.6(2) . . . . ?
C26 C21 C22 C23 -1.1(2) . . . . ?
Br1 C21 C22 C23 177.29(11) . . . . ?
C21 C22 C23 C24 0.2(2) . . . . ?
C22 C23 C24 C25 1.0(2) . . . . ?
C22 C23 C24 C27 -179.57(14) . . . . ?
C23 C24 C25 C26 -1.3(2) . . . . ?
C27 C24 C25 C26 179.31(14) . . . . ?
C22 C21 C26 C25 0.8(2) . . . . ?
Br1 C21 C26 C25 -177.56(11) . . . . ?
C24 C25 C26 C21 0.4(2) . . . . ?
C12 N11 C27 C24 122.20(16) . . . . ?
C19 N11 C27 C24 -54.8(2) . . . . ?
C25 C24 C27 N11 -47.02(19) . . . . ?
C23 C24 C27 N11 133.55(14) . . . . ?
C36 C31 C32 C33 0.0(2) . . . . ?
C37 C31 C32 C33 -179.35(14) . . . . ?
C31 C32 C33 C34 -0.7(2) . . . . ?
C32 C33 C34 C35 1.2(2) . . . . ?
C32 C33 C34 Br2 -176.98(12) . . . . ?
C33 C34 C35 C36 -0.8(2) . . . . ?
Br2 C34 C35 C36 177.35(12) . . . . ?
C34 C35 C36 C31 0.0(2) . . . . ?
C32 C31 C36 C35 0.4(2) . . . . ?
C37 C31 C36 C35 179.75(14) . . . . ?
C36 C31 C37 N37 176.15(14) . . . . ?
C32 C31 C37 N37 -4.5(2) . . . . ?
C36 C31 C37 C38 -5.0(2) . . . . ?
C32 C31 C37 C38 174.35(14) . . . . ?
C38 C37 N37 O37 0.1(2) . . . . ?
C31 C37 N37 O37 178.92(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O37 H37 N13 0.91(2) 1.73(2) 2.6260(18) 168(2) .

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        30.05
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.776
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.080

#END

data_A4
_database_code_depnum_ccdc_archive 'CCDC 694151'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
4-bromo-PhC(CN)(N=OH), (3-[(5,6-dimethylbenzimidazol-1-yl)methyl]PhCN
;
_chemical_name_common            
;4-bromo-PhC(CN)(N=OH), (3-((5,6-dimethylbenzimidazol-1-
yl)methyl)PhCN
;
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C8 H5 N2 O Br) (C17 H15 N3)
;
_chemical_formula_sum            'C25 H20 Br N5 O'
_chemical_formula_weight         486.37

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.039(3)
_cell_length_b                   13.982(6)
_cell_length_c                   14.166(6)
_cell_angle_alpha                70.067(19)
_cell_angle_beta                 83.78(3)
_cell_angle_gamma                82.22(3)
_cell_volume                     1111.6(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1383
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      18.50

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    1.877
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16974
_diffrn_reflns_av_R_equivalents  0.2759
_diffrn_reflns_av_sigmaI/netI    0.3704
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.53
_diffrn_reflns_theta_max         27.39
_reflns_number_total             4980
_reflns_number_gt                1475
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0700P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.059(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4980
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2524
_refine_ls_R_factor_gt           0.0716
_refine_ls_wR_factor_ref         0.2081
_refine_ls_wR_factor_gt          0.1546
_refine_ls_goodness_of_fit_ref   0.795
_refine_ls_restrained_S_all      0.795
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.87028(15) -0.02316(7) 0.27426(7) 0.0698(5) Uani 1 1 d . . .
N11 N 0.2436(9) 0.5147(4) 0.3121(4) 0.0393(15) Uani 1 1 d . . .
C12 C 0.3975(11) 0.4939(6) 0.3819(6) 0.046(2) Uani 1 1 d . . .
H12 H 0.3778 0.5204 0.4361 0.055 Uiso 1 1 calc R . .
N13 N 0.5742(9) 0.4345(4) 0.3675(4) 0.0394(15) Uani 1 1 d . . .
C14 C 0.5398(10) 0.4154(5) 0.2800(5) 0.0313(17) Uani 1 1 d . . .
C15 C 0.6713(11) 0.3583(5) 0.2282(5) 0.0367(18) Uani 1 1 d . . .
H15 H 0.8156 0.3274 0.2494 0.044 Uiso 1 1 calc R . .
C16 C 0.5925(11) 0.3467(5) 0.1464(5) 0.0374(18) Uani 1 1 d . . .
C17 C 0.3817(11) 0.3987(5) 0.1116(5) 0.0364(18) Uani 1 1 d . . .
C18 C 0.2526(11) 0.4570(5) 0.1621(5) 0.0386(18) Uani 1 1 d . . .
H18 H 0.1108 0.4908 0.1399 0.046 Uiso 1 1 calc R . .
C19 C 0.3351(10) 0.4651(5) 0.2459(5) 0.0322(17) Uani 1 1 d . . .
C20 C 0.7284(12) 0.2818(6) 0.0915(5) 0.049(2) Uani 1 1 d . . .
H20A H 0.8762 0.2596 0.1188 0.074 Uiso 1 1 calc R . .
H20B H 0.7462 0.3217 0.0197 0.074 Uiso 1 1 calc R . .
H20C H 0.6517 0.2217 0.0999 0.074 Uiso 1 1 calc R . .
C21 C 0.3023(12) 0.3865(6) 0.0206(5) 0.049(2) Uani 1 1 d . . .
H21A H 0.1495 0.4203 0.0098 0.074 Uiso 1 1 calc R . .
H21B H 0.3035 0.3136 0.0304 0.074 Uiso 1 1 calc R . .
H21C H 0.4016 0.4178 -0.0383 0.074 Uiso 1 1 calc R . .
C31 C -0.0516(11) 0.8194(6) 0.0754(6) 0.0377(18) Uani 1 1 d . . .
C32 C -0.0838(10) 0.7282(6) 0.1497(5) 0.0344(17) Uani 1 1 d . . .
H32 H -0.2107 0.6945 0.1506 0.041 Uiso 1 1 calc R . .
C33 C 0.0669(10) 0.6850(5) 0.2236(5) 0.0337(17) Uani 1 1 d . . .
C34 C 0.2479(11) 0.7397(6) 0.2223(6) 0.046(2) Uani 1 1 d . . .
H34 H 0.3500 0.7130 0.2739 0.055 Uiso 1 1 calc R . .
C35 C 0.2785(12) 0.8302(6) 0.1482(6) 0.046(2) Uani 1 1 d . . .
H35 H 0.4026 0.8654 0.1480 0.056 Uiso 1 1 calc R . .
C36 C 0.1295(12) 0.8713(6) 0.0730(6) 0.046(2) Uani 1 1 d . . .
H36 H 0.1514 0.9341 0.0208 0.055 Uiso 1 1 calc R . .
C37 C -0.2049(14) 0.8626(6) -0.0011(7) 0.048(2) Uani 1 1 d . . .
N37 N -0.3323(12) 0.9012(5) -0.0629(5) 0.059(2) Uani 1 1 d . . .
C38 C 0.0379(10) 0.5844(5) 0.3056(5) 0.0370(18) Uani 1 1 d . . .
H38A H -0.0006 0.5960 0.3708 0.044 Uiso 1 1 calc R . .
H38B H -0.0868 0.5531 0.2914 0.044 Uiso 1 1 calc R . .
C41 C 1.3779(11) 0.1796(5) 0.4220(5) 0.0339(17) Uani 1 1 d . . .
C42 C 1.3148(12) 0.1538(5) 0.3447(5) 0.0419(19) Uani 1 1 d . . .
H42 H 1.1682 0.1769 0.3222 0.050 Uiso 1 1 calc R . .
C43 C 1.4590(12) 0.0949(6) 0.2981(5) 0.047(2) Uani 1 1 d . . .
H43 H 1.4161 0.0806 0.2421 0.056 Uiso 1 1 calc R . .
C44 C 1.6683(12) 0.0572(5) 0.3359(6) 0.0422(19) Uani 1 1 d . . .
C45 C 1.7330(12) 0.0804(6) 0.4144(6) 0.048(2) Uani 1 1 d . . .
H45 H 1.8766 0.0543 0.4393 0.058 Uiso 1 1 calc R . .
C46 C 1.5890(11) 0.1418(6) 0.4576(6) 0.047(2) Uani 1 1 d . . .
H46 H 1.6344 0.1583 0.5119 0.056 Uiso 1 1 calc R . .
C47 C 1.2305(11) 0.2470(5) 0.4664(5) 0.0347(18) Uani 1 1 d . . .
N47 N 1.0380(9) 0.2893(5) 0.4295(4) 0.0423(15) Uani 1 1 d . . .
O47 O 0.9228(7) 0.3514(4) 0.4782(3) 0.0457(13) Uani 1 1 d . . .
H47 H 0.8012 0.3766 0.4515 0.069 Uiso 1 1 calc R . .
C48 C 1.3040(11) 0.2691(6) 0.5517(6) 0.043(2) Uani 1 1 d . . .
N48 N 1.3630(9) 0.2891(5) 0.6150(5) 0.059(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C44 1.892(7) . ?
N11 C12 1.362(8) . ?
N11 C19 1.376(8) . ?
N11 C38 1.462(8) . ?
C12 N13 1.303(8) . ?
C12 H12 0.9500 . ?
N13 C14 1.396(8) . ?
C14 C15 1.381(9) . ?
C14 C19 1.383(8) . ?
C15 C16 1.365(9) . ?
C15 H15 0.9500 . ?
C16 C17 1.426(9) . ?
C16 C20 1.498(9) . ?
C17 C18 1.375(9) . ?
C17 C21 1.492(9) . ?
C18 C19 1.381(9) . ?
C18 H18 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C31 C32 1.370(9) . ?
C31 C36 1.384(9) . ?
C31 C37 1.420(11) . ?
C32 C33 1.384(9) . ?
C32 H32 0.9500 . ?
C33 C34 1.412(9) . ?
C33 C38 1.507(9) . ?
C34 C35 1.361(10) . ?
C34 H34 0.9500 . ?
C35 C36 1.387(10) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 N37 1.166(9) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C41 C42 1.369(9) . ?
C41 C46 1.391(9) . ?
C41 C47 1.459(9) . ?
C42 C43 1.387(9) . ?
C42 H42 0.9500 . ?
C43 C44 1.391(9) . ?
C43 H43 0.9500 . ?
C44 C45 1.368(10) . ?
C45 C46 1.381(10) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 N47 1.307(8) . ?
C47 C48 1.470(10) . ?
N47 O47 1.362(7) . ?
O47 H47 0.8400 . ?
C48 N48 1.130(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N11 C19 105.4(6) . . ?
C12 N11 C38 125.7(6) . . ?
C19 N11 C38 128.6(6) . . ?
N13 C12 N11 113.9(6) . . ?
N13 C12 H12 123.0 . . ?
N11 C12 H12 123.0 . . ?
C12 N13 C14 104.9(6) . . ?
C15 C14 C19 120.2(6) . . ?
C15 C14 N13 131.0(6) . . ?
C19 C14 N13 108.8(6) . . ?
C16 C15 C14 119.5(6) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 119.8(6) . . ?
C15 C16 C20 120.5(7) . . ?
C17 C16 C20 119.7(7) . . ?
C18 C17 C16 120.6(7) . . ?
C18 C17 C21 120.8(7) . . ?
C16 C17 C21 118.6(6) . . ?
C17 C18 C19 118.1(7) . . ?
C17 C18 H18 121.0 . . ?
C19 C18 H18 121.0 . . ?
N11 C19 C18 131.2(6) . . ?
N11 C19 C14 107.0(6) . . ?
C18 C19 C14 121.7(6) . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C32 C31 C36 121.1(7) . . ?
C32 C31 C37 120.3(7) . . ?
C36 C31 C37 118.6(7) . . ?
C31 C32 C33 120.5(6) . . ?
C31 C32 H32 119.7 . . ?
C33 C32 H32 119.7 . . ?
C32 C33 C34 118.0(7) . . ?
C32 C33 C38 121.9(6) . . ?
C34 C33 C38 120.1(6) . . ?
C35 C34 C33 120.9(7) . . ?
C35 C34 H34 119.5 . . ?
C33 C34 H34 119.5 . . ?
C34 C35 C36 120.4(7) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C31 C36 C35 118.9(7) . . ?
C31 C36 H36 120.6 . . ?
C35 C36 H36 120.6 . . ?
N37 C37 C31 177.5(8) . . ?
N11 C38 C33 110.5(5) . . ?
N11 C38 H38A 109.5 . . ?
C33 C38 H38A 109.5 . . ?
N11 C38 H38B 109.5 . . ?
C33 C38 H38B 109.5 . . ?
H38A C38 H38B 108.1 . . ?
C42 C41 C46 118.9(7) . . ?
C42 C41 C47 121.5(6) . . ?
C46 C41 C47 119.6(7) . . ?
C41 C42 C43 121.8(7) . . ?
C41 C42 H42 119.1 . . ?
C43 C42 H42 119.1 . . ?
C42 C43 C44 118.0(7) . . ?
C42 C43 H43 121.0 . . ?
C44 C43 H43 121.0 . . ?
C45 C44 C43 121.0(7) . . ?
C45 C44 Br1 119.6(6) . . ?
C43 C44 Br1 119.4(6) . . ?
C44 C45 C46 119.9(7) . . ?
C44 C45 H45 120.1 . . ?
C46 C45 H45 120.1 . . ?
C45 C46 C41 120.3(7) . . ?
C45 C46 H46 119.9 . . ?
C41 C46 H46 119.9 . . ?
N47 C47 C41 120.7(6) . . ?
N47 C47 C48 120.1(6) . . ?
C41 C47 C48 119.1(6) . . ?
C47 N47 O47 113.4(6) . . ?
N47 O47 H47 109.5 . . ?
N48 C48 C47 177.6(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C19 N11 C12 N13 -1.4(8) . . . . ?
C38 N11 C12 N13 -175.5(6) . . . . ?
N11 C12 N13 C14 1.4(8) . . . . ?
C12 N13 C14 C15 179.4(7) . . . . ?
C12 N13 C14 C19 -0.8(8) . . . . ?
C19 C14 C15 C16 -3.6(10) . . . . ?
N13 C14 C15 C16 176.2(7) . . . . ?
C14 C15 C16 C17 3.9(10) . . . . ?
C14 C15 C16 C20 -177.6(6) . . . . ?
C15 C16 C17 C18 -2.7(10) . . . . ?
C20 C16 C17 C18 178.8(6) . . . . ?
C15 C16 C17 C21 178.6(6) . . . . ?
C20 C16 C17 C21 0.0(10) . . . . ?
C16 C17 C18 C19 1.2(10) . . . . ?
C21 C17 C18 C19 179.9(6) . . . . ?
C12 N11 C19 C18 178.2(7) . . . . ?
C38 N11 C19 C18 -7.9(12) . . . . ?
C12 N11 C19 C14 0.8(7) . . . . ?
C38 N11 C19 C14 174.7(6) . . . . ?
C17 C18 C19 N11 -177.9(7) . . . . ?
C17 C18 C19 C14 -0.9(10) . . . . ?
C15 C14 C19 N11 179.8(6) . . . . ?
N13 C14 C19 N11 0.0(7) . . . . ?
C15 C14 C19 C18 2.1(10) . . . . ?
N13 C14 C19 C18 -177.7(6) . . . . ?
C36 C31 C32 C33 -1.1(10) . . . . ?
C37 C31 C32 C33 179.0(6) . . . . ?
C31 C32 C33 C34 2.7(9) . . . . ?
C31 C32 C33 C38 -179.2(6) . . . . ?
C32 C33 C34 C35 -2.7(10) . . . . ?
C38 C33 C34 C35 179.2(6) . . . . ?
C33 C34 C35 C36 1.0(11) . . . . ?
C32 C31 C36 C35 -0.6(10) . . . . ?
C37 C31 C36 C35 179.2(7) . . . . ?
C34 C35 C36 C31 0.7(11) . . . . ?
C12 N11 C38 C33 101.6(8) . . . . ?
C19 N11 C38 C33 -71.1(8) . . . . ?
C32 C33 C38 N11 128.6(6) . . . . ?
C34 C33 C38 N11 -53.4(8) . . . . ?
C46 C41 C42 C43 -2.9(10) . . . . ?
C47 C41 C42 C43 176.1(6) . . . . ?
C41 C42 C43 C44 3.5(10) . . . . ?
C42 C43 C44 C45 -2.2(11) . . . . ?
C42 C43 C44 Br1 -179.8(5) . . . . ?
C43 C44 C45 C46 0.2(11) . . . . ?
Br1 C44 C45 C46 177.9(5) . . . . ?
C44 C45 C46 C41 0.5(11) . . . . ?
C42 C41 C46 C45 0.9(10) . . . . ?
C47 C41 C46 C45 -178.1(7) . . . . ?
C42 C41 C47 N47 -3.9(10) . . . . ?
C46 C41 C47 N47 175.1(6) . . . . ?
C42 C41 C47 C48 177.8(6) . . . . ?
C46 C41 C47 C48 -3.2(10) . . . . ?
C41 C47 N47 O47 -178.8(5) . . . . ?
C48 C47 N47 O47 -0.5(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O47 H47 N13 0.84 1.83 2.656(7) 167.3 .

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.39
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.789
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.157

#END

data_B5
_database_code_depnum_ccdc_archive 'CCDC 694152'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
[2-fluoro-PhC(CN)(=NOH)]2, 1,2-di(4-pyridyl)ethene
;
_chemical_name_common            
'(2-fluoro-PhC(CN)(=NOH))2, 1,2-di(4-pyridyl)ethene'
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C8 H5 N2 O F)2 (C12 H10 N2)
;
_chemical_formula_sum            'C28 H20 F2 N6 O2'
_chemical_formula_weight         510.50

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   3.8189(6)
_cell_length_b                   11.2941(18)
_cell_length_c                   14.107(2)
_cell_angle_alpha                98.884(10)
_cell_angle_beta                 93.147(11)
_cell_angle_gamma                94.624(10)
_cell_volume                     597.79(16)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    783
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      26.70

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             264
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4295
_diffrn_reflns_av_R_equivalents  0.1106
_diffrn_reflns_av_sigmaI/netI    0.0972
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.46
_diffrn_reflns_theta_max         27.47
_reflns_number_total             2606
_reflns_number_gt                1734
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2606
_refine_ls_number_parameters     180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1754
_refine_ls_wR_factor_gt          0.1588
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C11 C 0.9413(5) 0.26002(18) 0.58790(14) 0.0299(5) Uani 1 1 d . . .
C12A C 1.1167(5) 0.3527(2) 0.55049(16) 0.0365(5) Uani 0.669(2) 1 d P A 1
F12 F 1.2186(6) 0.45468(18) 0.60662(15) 0.0501(5) Uani 0.669(2) 1 d P A 1
C12B C 1.1167(5) 0.3527(2) 0.55049(16) 0.0365(5) Uani 0.331(2) 1 d P A 2
H12 H 1.1889 0.4261 0.5921 0.044 Uiso 0.331(2) 1 calc PR A 2
C13 C 1.1896(6) 0.3426(2) 0.45607(17) 0.0442(6) Uani 1 1 d . . .
H13 H 1.3081 0.4083 0.4326 0.053 Uiso 1 1 calc R A 1
C14 C 1.0892(6) 0.2360(3) 0.39513(17) 0.0478(6) Uani 1 1 d . A .
H14 H 1.1426 0.2277 0.3296 0.057 Uiso 1 1 calc R . .
C15 C 0.9126(6) 0.1416(2) 0.42864(16) 0.0453(6) Uani 1 1 d . . .
H15 H 0.8397 0.0687 0.3865 0.054 Uiso 1 1 calc R A 1
C16A C 0.8432(5) 0.1545(2) 0.52396(16) 0.0378(5) Uani 0.669(2) 1 d P A 1
H16 H 0.7236 0.0888 0.5471 0.045 Uiso 0.669(2) 1 calc PR A 1
C16B C 0.8432(5) 0.1545(2) 0.52396(16) 0.0378(5) Uani 0.331(2) 1 d P A 2
F16 F 0.6496(11) 0.0710(4) 0.5501(3) 0.0501(5) Uani 0.331(2) 1 d P A 2
C17 C 0.8569(5) 0.27048(18) 0.68908(14) 0.0315(5) Uani 1 1 d . A .
N17 N 0.8017(4) 0.37374(17) 0.73653(12) 0.0365(5) Uani 1 1 d . . .
O17 O 0.7233(4) 0.36743(16) 0.82888(11) 0.0442(4) Uani 1 1 d . A .
H17 H 0.675(7) 0.455(3) 0.851(2) 0.066(9) Uiso 1 1 d . . .
C18 C 0.8337(6) 0.1630(2) 0.73340(16) 0.0428(6) Uani 1 1 d . . .
N18 N 0.8214(8) 0.0771(2) 0.76621(17) 0.0707(8) Uani 1 1 d . A .
N21 N 0.6016(5) 0.59158(17) 0.88855(13) 0.0390(5) Uani 1 1 d . . .
C22 C 0.4607(6) 0.6538(2) 0.82510(16) 0.0424(6) Uani 1 1 d . . .
H22 H 0.3870 0.6126 0.7624 0.051 Uiso 1 1 calc R . .
C23 C 0.4173(6) 0.7738(2) 0.84592(15) 0.0387(5) Uani 1 1 d . . .
H23 H 0.3183 0.8137 0.7977 0.046 Uiso 1 1 calc R . .
C24 C 0.5165(5) 0.83774(19) 0.93681(14) 0.0314(5) Uani 1 1 d . . .
C25 C 0.6635(5) 0.7723(2) 1.00309(15) 0.0358(5) Uani 1 1 d . . .
H25 H 0.7371 0.8109 1.0666 0.043 Uiso 1 1 calc R . .
C26 C 0.7011(6) 0.6522(2) 0.97607(15) 0.0363(5) Uani 1 1 d . . .
H26 H 0.8036 0.6098 1.0222 0.044 Uiso 1 1 calc R . .
C27 C 0.4593(5) 0.96438(19) 0.95824(15) 0.0337(5) Uani 1 1 d . . .
H27 H 0.3542 0.9993 0.9079 0.040 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C11 C12A 1.385(3) . ?
C11 C16A 1.391(3) . ?
C11 C17 1.470(3) . ?
C12A F12 1.310(3) . ?
C12A C13 1.365(3) . ?
C13 C14 1.381(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.374(4) . ?
C14 H14 0.9500 . ?
C15 C16A 1.373(3) . ?
C15 H15 0.9500 . ?
C16A H16 0.9500 . ?
C17 N17 1.291(3) . ?
C17 C18 1.447(3) . ?
N17 O17 1.364(2) . ?
O17 H17 1.03(3) . ?
C18 N18 1.136(3) . ?
N21 C26 1.335(3) . ?
N21 C22 1.337(3) . ?
C22 C23 1.367(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.388(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.399(3) . ?
C24 C27 1.452(3) . ?
C25 C26 1.373(3) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C27 1.326(4) 2_677 ?
C27 H27 0.9500 . ?

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
C12A C11 C16A 116.4(2) . . ?
C12A C11 C17 122.95(18) . . ?
C16A C11 C17 120.66(19) . . ?
F12 C12A C13 117.7(2) . . ?
F12 C12A C11 119.8(2) . . ?
C13 C12A C11 122.5(2) . . ?
C12A C13 C14 119.2(2) . . ?
C12A C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 120.5(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16A C15 C14 118.9(2) . . ?
C16A C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16A C11 122.5(2) . . ?
C15 C16A H16 118.8 . . ?
C11 C16A H16 118.8 . . ?
N17 C17 C18 121.17(19) . . ?
N17 C17 C11 120.14(19) . . ?
C18 C17 C11 118.69(18) . . ?
C17 N17 O17 112.64(18) . . ?
N17 O17 H17 99.6(16) . . ?
N18 C18 C17 178.0(3) . . ?
C26 N21 C22 116.81(19) . . ?
N21 C22 C23 123.3(2) . . ?
N21 C22 H22 118.4 . . ?
C23 C22 H22 118.4 . . ?
C22 C23 C24 120.6(2) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C23 C24 C25 116.0(2) . . ?
C23 C24 C27 119.74(19) . . ?
C25 C24 C27 124.27(19) . . ?
C26 C25 C24 119.76(19) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
N21 C26 C25 123.6(2) . . ?
N21 C26 H26 118.2 . . ?
C25 C26 H26 118.2 . . ?
C27 C27 C24 125.9(3) 2_677 . ?
C27 C27 H27 117.1 2_677 . ?
C24 C27 H27 117.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16A C11 C12A F12 -179.7(2) . . . . ?
C17 C11 C12A F12 0.9(3) . . . . ?
C16A C11 C12A C13 0.3(3) . . . . ?
C17 C11 C12A C13 -179.09(19) . . . . ?
F12 C12A C13 C14 179.3(2) . . . . ?
C11 C12A C13 C14 -0.7(3) . . . . ?
C12A C13 C14 C15 1.1(3) . . . . ?
C13 C14 C15 C16A -1.1(4) . . . . ?
C14 C15 C16A C11 0.8(3) . . . . ?
C12A C11 C16A C15 -0.4(3) . . . . ?
C17 C11 C16A C15 179.1(2) . . . . ?
C12A C11 C17 N17 29.8(3) . . . . ?
C16A C11 C17 N17 -149.6(2) . . . . ?
C12A C11 C17 C18 -150.8(2) . . . . ?
C16A C11 C17 C18 29.8(3) . . . . ?
C18 C17 N17 O17 0.0(3) . . . . ?
C11 C17 N17 O17 179.37(16) . . . . ?
C26 N21 C22 C23 0.2(3) . . . . ?
N21 C22 C23 C24 -0.8(4) . . . . ?
C22 C23 C24 C25 0.7(3) . . . . ?
C22 C23 C24 C27 -178.3(2) . . . . ?
C23 C24 C25 C26 -0.1(3) . . . . ?
C27 C24 C25 C26 178.9(2) . . . . ?
C22 N21 C26 C25 0.5(3) . . . . ?
C24 C25 C26 N21 -0.5(3) . . . . ?
C23 C24 C27 C27 179.8(3) . . . 2_677 ?
C25 C24 C27 C27 0.9(4) . . . 2_677 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O17 H17 N21 1.03(3) 1.60(3) 2.628(3) 178(3) .

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.070

#END

data_C6
_database_code_depnum_ccdc_archive 'CCDC 694153'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
481 1,4-di[(1-benzimidazolyl)methyl]benzene, [3-chloro-PhC(CN)(=NOH)]2
;
_chemical_name_common            
;481 1,4-di((1-benzimidazolyl)methyl)benzene, (3-chloro-
PhC(CN)(=NOH))2
;
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C22 H18 N4) (C8 H5 N2 O Cl)2
;
_chemical_formula_sum            'C38 H28 Cl2 N8 O2'
_chemical_formula_weight         699.58

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   13.6335(10)
_cell_length_b                   4.4402(3)
_cell_length_c                   27.297(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.084(3)
_cell_angle_gamma                90.00
_cell_volume                     1648.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9905
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      30.52

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             724
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9297
_exptl_absorpt_correction_T_max  0.9639
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            40395
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         30.99
_reflns_number_total             5259
_reflns_number_gt                3883
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0500P)²+0.4000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5259
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1118
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.15560(2) -0.38771(8) 0.668525(14) 0.03458(11) Uani 1 1 d . . .
N11 N 0.81489(7) 1.1873(2) 0.58747(4) 0.0182(2) Uani 1 1 d . . .
C12 C 0.72093(9) 1.1275(3) 0.57020(5) 0.0214(3) Uani 1 1 d . . .
H12 H 0.6906 1.2177 0.5414 0.026 Uiso 1 1 calc R . .
N13 N 0.67622(8) 0.9328(2) 0.59718(4) 0.0233(2) Uani 1 1 d . . .
C14 C 0.74478(9) 0.8585(3) 0.63534(5) 0.0204(2) Uani 1 1 d . . .
C15 C 0.73689(10) 0.6647(3) 0.67527(5) 0.0256(3) Uani 1 1 d . . .
H15 H 0.6777 0.5586 0.6798 0.031 Uiso 1 1 calc R . .
C16 C 0.81842(11) 0.6334(3) 0.70785(5) 0.0277(3) Uani 1 1 d . . .
H16 H 0.8150 0.5043 0.7354 0.033 Uiso 1 1 calc R . .
C17 C 0.90642(11) 0.7882(3) 0.70114(5) 0.0270(3) Uani 1 1 d . . .
H17 H 0.9612 0.7591 0.7242 0.032 Uiso 1 1 calc R . .
C18 C 0.91557(10) 0.9816(3) 0.66199(5) 0.0232(3) Uani 1 1 d . . .
H18 H 0.9750 1.0865 0.6576 0.028 Uiso 1 1 calc R . .
C19 C 0.83288(9) 1.0142(2) 0.62942(4) 0.0189(2) Uani 1 1 d . . .
C21 C 0.94631(9) 1.1832(2) 0.53029(4) 0.0178(2) Uani 1 1 d . . .
C22 C 0.90590(9) 1.0914(3) 0.48470(5) 0.0237(3) Uani 1 1 d . . .
H22 H 0.8413 1.1537 0.4739 0.028 Uiso 1 1 calc R . .
C26 C 1.04110(9) 1.0909(3) 0.54535(5) 0.0241(3) Uani 1 1 d . . .
H26 H 1.0699 1.1528 0.5764 0.029 Uiso 1 1 calc R . .
C27 C 0.88620(9) 1.3722(2) 0.56318(5) 0.0194(2) Uani 1 1 d . . .
H27A H 0.9306 1.4729 0.5884 0.023 Uiso 1 1 calc R . .
H27B H 0.8509 1.5303 0.5434 0.023 Uiso 1 1 calc R . .
C31 C 0.39381(9) 0.0837(2) 0.63858(5) 0.0192(2) Uani 1 1 d . . .
C32 C 0.29964(9) -0.0411(3) 0.63599(5) 0.0213(2) Uani 1 1 d . . .
H32 H 0.2532 0.0096 0.6097 0.026 Uiso 1 1 calc R . .
C33 C 0.27460(9) -0.2398(3) 0.67222(5) 0.0235(3) Uani 1 1 d . . .
C34 C 0.34031(11) -0.3196(3) 0.71095(5) 0.0271(3) Uani 1 1 d . . .
H34 H 0.3218 -0.4550 0.7356 0.033 Uiso 1 1 calc R . .
C35 C 0.43433(10) -0.1962(3) 0.71281(5) 0.0274(3) Uani 1 1 d . . .
H35 H 0.4807 -0.2497 0.7390 0.033 Uiso 1 1 calc R . .
C36 C 0.46150(10) 0.0026(3) 0.67731(5) 0.0239(3) Uani 1 1 d . . .
H36 H 0.5261 0.0843 0.6792 0.029 Uiso 1 1 calc R . .
C37 C 0.42049(9) 0.2999(3) 0.60091(5) 0.0196(2) Uani 1 1 d . . .
N37 N 0.50121(8) 0.4531(2) 0.60675(4) 0.0223(2) Uani 1 1 d . . .
O37 O 0.51284(7) 0.6451(2) 0.56870(3) 0.0260(2) Uani 1 1 d . . .
H37 H 0.5728(12) 0.749(4) 0.5792(5) 0.031 Uiso 1 1 d . . .
C38 C 0.35289(9) 0.3460(3) 0.55810(5) 0.0234(3) Uani 1 1 d . . .
N38 N 0.29706(9) 0.3799(3) 0.52529(5) 0.0340(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C33 1.7465(13) . ?
N11 C12 1.3594(16) . ?
N11 C19 1.3863(15) . ?
N11 C27 1.4666(15) . ?
C12 N13 1.3135(16) . ?
C12 H12 0.9500 . ?
N13 C14 1.3887(17) . ?
C14 C15 1.3990(17) . ?
C14 C19 1.4051(17) . ?
C15 C16 1.380(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.406(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.3836(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.3926(18) . ?
C18 H18 0.9500 . ?
C21 C22 1.3857(18) . ?
C21 C26 1.3897(17) . ?
C21 C27 1.5123(16) . ?
C22 C26 1.3911(17) 3_776 ?
C22 H22 0.9500 . ?
C26 C22 1.3911(17) 3_776 ?
C26 H26 0.9500 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C31 C32 1.3954(17) . ?
C31 C36 1.4001(17) . ?
C31 C37 1.4711(17) . ?
C32 C33 1.3859(17) . ?
C32 H32 0.9500 . ?
C33 C34 1.3823(19) . ?
C34 C35 1.392(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.3806(19) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 N37 1.2939(16) . ?
C37 C38 1.4504(18) . ?
N37 O37 1.3618(14) . ?
O37 H37 0.965(16) . ?
C38 N38 1.1433(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N11 C19 106.57(10) . . ?
C12 N11 C27 126.24(10) . . ?
C19 N11 C27 126.86(10) . . ?
N13 C12 N11 113.42(11) . . ?
N13 C12 H12 123.3 . . ?
N11 C12 H12 123.3 . . ?
C12 N13 C14 105.22(10) . . ?
N13 C14 C15 130.20(12) . . ?
N13 C14 C19 109.40(11) . . ?
C15 C14 C19 120.40(12) . . ?
C16 C15 C14 117.45(12) . . ?
C16 C15 H15 121.3 . . ?
C14 C15 H15 121.3 . . ?
C15 C16 C17 121.49(12) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C18 C17 C16 121.93(13) . . ?
C18 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
C17 C18 C19 116.37(12) . . ?
C17 C18 H18 121.8 . . ?
C19 C18 H18 121.8 . . ?
N11 C19 C18 132.25(11) . . ?
N11 C19 C14 105.38(10) . . ?
C18 C19 C14 122.36(11) . . ?
C22 C21 C26 118.74(11) . . ?
C22 C21 C27 119.91(11) . . ?
C26 C21 C27 121.32(11) . . ?
C21 C22 C26 120.71(11) . 3_776 ?
C21 C22 H22 119.6 . . ?
C26 C22 H22 119.6 3_776 . ?
C21 C26 C22 120.55(12) . 3_776 ?
C21 C26 H26 119.7 . . ?
C22 C26 H26 119.7 3_776 . ?
N11 C27 C21 111.25(9) . . ?
N11 C27 H27A 109.4 . . ?
C21 C27 H27A 109.4 . . ?
N11 C27 H27B 109.4 . . ?
C21 C27 H27B 109.4 . . ?
H27A C27 H27B 108.0 . . ?
C32 C31 C36 119.39(11) . . ?
C32 C31 C37 119.75(11) . . ?
C36 C31 C37 120.87(11) . . ?
C33 C32 C31 119.29(12) . . ?
C33 C32 H32 120.4 . . ?
C31 C32 H32 120.4 . . ?
C34 C33 C32 121.98(12) . . ?
C34 C33 Cl1 119.77(10) . . ?
C32 C33 Cl1 118.24(10) . . ?
C33 C34 C35 118.17(12) . . ?
C33 C34 H34 120.9 . . ?
C35 C34 H34 120.9 . . ?
C36 C35 C34 121.24(12) . . ?
C36 C35 H35 119.4 . . ?
C34 C35 H35 119.4 . . ?
C35 C36 C31 119.93(12) . . ?
C35 C36 H36 120.0 . . ?
C31 C36 H36 120.0 . . ?
N37 C37 C38 120.74(11) . . ?
N37 C37 C31 120.49(11) . . ?
C38 C37 C31 118.72(10) . . ?
C37 N37 O37 112.30(10) . . ?
N37 O37 H37 102.4(9) . . ?
N38 C38 C37 177.71(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C19 N11 C12 N13 0.27(14) . . . . ?
C27 N11 C12 N13 174.02(10) . . . . ?
N11 C12 N13 C14 0.41(14) . . . . ?
C12 N13 C14 C15 179.04(12) . . . . ?
C12 N13 C14 C19 -0.93(13) . . . . ?
N13 C14 C15 C16 179.78(12) . . . . ?
C19 C14 C15 C16 -0.26(18) . . . . ?
C14 C15 C16 C17 -0.45(19) . . . . ?
C15 C16 C17 C18 0.7(2) . . . . ?
C16 C17 C18 C19 -0.19(19) . . . . ?
C12 N11 C19 C18 179.57(13) . . . . ?
C27 N11 C19 C18 5.9(2) . . . . ?
C12 N11 C19 C14 -0.82(12) . . . . ?
C27 N11 C19 C14 -174.51(10) . . . . ?
C17 C18 C19 N11 179.02(12) . . . . ?
C17 C18 C19 C14 -0.54(18) . . . . ?
N13 C14 C19 N11 1.09(13) . . . . ?
C15 C14 C19 N11 -178.88(10) . . . . ?
N13 C14 C19 C18 -179.25(11) . . . . ?
C15 C14 C19 C18 0.78(18) . . . . ?
C26 C21 C22 C26 0.3(2) . . . 3_776 ?
C27 C21 C22 C26 -177.82(11) . . . 3_776 ?
C22 C21 C26 C22 -0.3(2) . . . 3_776 ?
C27 C21 C26 C22 177.79(11) . . . 3_776 ?
C12 N11 C27 C21 -90.67(14) . . . . ?
C19 N11 C27 C21 81.83(14) . . . . ?
C22 C21 C27 N11 77.61(14) . . . . ?
C26 C21 C27 N11 -100.49(13) . . . . ?
C36 C31 C32 C33 0.87(17) . . . . ?
C37 C31 C32 C33 -178.68(11) . . . . ?
C31 C32 C33 C34 -0.22(18) . . . . ?
C31 C32 C33 Cl1 179.00(9) . . . . ?
C32 C33 C34 C35 -0.48(19) . . . . ?
Cl1 C33 C34 C35 -179.70(10) . . . . ?
C33 C34 C35 C36 0.54(19) . . . . ?
C34 C35 C36 C31 0.10(19) . . . . ?
C32 C31 C36 C35 -0.81(18) . . . . ?
C37 C31 C36 C35 178.73(11) . . . . ?
C32 C31 C37 N37 169.05(11) . . . . ?
C36 C31 C37 N37 -10.49(17) . . . . ?
C32 C31 C37 C38 -8.65(17) . . . . ?
C36 C31 C37 C38 171.81(11) . . . . ?
C38 C37 N37 O37 -1.28(16) . . . . ?
C31 C37 N37 O37 -178.93(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O37 H37 N13 0.965(16) 1.672(16) 2.6365(14) 179.5(17) .

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.055

#END

data_D7
_database_code_depnum_ccdc_archive 'CCDC 694154'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
MS 512 1-(4-pyridylmethyl)-5,6-Me2benzimidazole, 4-F-PhC(CN)(NOH)
;
_chemical_name_common            
;MS 512 1-(4-pyridylmethyl)-5,6-Me2benzimidazole, 4-F-
PhC(CN)(NOH)
;
_chemical_melting_point          ?
_chemical_formula_moiety         
;
(C15 H15 N3) (C8 H5 N2 O F)
;
_chemical_formula_sum            'C23 H20 F N5 O'
_chemical_formula_weight         401.44

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   16.1659(12)
_cell_length_b                   6.4146(5)
_cell_length_c                   21.0074(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.945(5)
_cell_angle_gamma                90.00
_cell_volume                     2094.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2093
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      21.51

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20522
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_sigmaI/netI    0.0808
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.42
_diffrn_reflns_theta_max         30.50
_reflns_number_total             6367
_reflns_number_gt                2616
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0500P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6367
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1597
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1323
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_restrained_S_all      0.945
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.37443(5) -0.11599(11) 0.66110(4) 0.0433(2) Uani 1 1 d . . .
C12 C 0.33642(6) 0.04439(15) 0.68356(5) 0.0471(3) Uani 1 1 d . . .
H12 H 0.3285 0.0481 0.7267 0.056 Uiso 1 1 calc R . .
N13 N 0.31126(5) 0.19532(12) 0.64008(4) 0.0473(2) Uani 1 1 d . . .
C14 C 0.33472(5) 0.12780(14) 0.58411(4) 0.0415(3) Uani 1 1 d . . .
C15 C 0.32266(6) 0.22021(16) 0.52226(5) 0.0514(3) Uani 1 1 d . . .
H15 H 0.2968 0.3539 0.5136 0.062 Uiso 1 1 calc R . .
C16 C 0.34871(6) 0.11554(17) 0.47375(5) 0.0562(3) Uani 1 1 d . . .
C17 C 0.38679(6) -0.08472(17) 0.48665(5) 0.0577(3) Uani 1 1 d . . .
C18 C 0.39997(6) -0.17632(16) 0.54824(5) 0.0523(3) Uani 1 1 d . . .
H18 H 0.4262 -0.3096 0.5574 0.063 Uiso 1 1 calc R . .
C19 C 0.37353(5) -0.06661(14) 0.59649(4) 0.0410(3) Uani 1 1 d . . .
C20 C 0.33338(8) 0.2124(2) 0.40594(5) 0.0862(5) Uani 1 1 d . . .
H20A H 0.3042 0.3467 0.4050 0.129 Uiso 1 1 calc R . .
H20B H 0.2974 0.1193 0.3727 0.129 Uiso 1 1 calc R . .
H20C H 0.3886 0.2341 0.3962 0.129 Uiso 1 1 calc R . .
C21 C 0.41269(8) -0.2031(2) 0.43241(6) 0.0892(4) Uani 1 1 d . . .
H21A H 0.4373 -0.3382 0.4496 0.134 Uiso 1 1 calc R . .
H21B H 0.4556 -0.1221 0.4178 0.134 Uiso 1 1 calc R . .
H21C H 0.3619 -0.2252 0.3949 0.134 Uiso 1 1 calc R . .
N31 N 0.68684(5) -0.32521(13) 0.76207(4) 0.0563(3) Uani 1 1 d . . .
C32 C 0.64314(6) -0.15064(16) 0.76540(5) 0.0563(3) Uani 1 1 d . . .
H32 H 0.6750 -0.0294 0.7829 0.068 Uiso 1 1 calc R . .
C33 C 0.55466(6) -0.13526(15) 0.74501(5) 0.0514(3) Uani 1 1 d . . .
H33 H 0.5272 -0.0070 0.7491 0.062 Uiso 1 1 calc R . .
C34 C 0.50646(6) -0.30795(14) 0.71862(4) 0.0422(3) Uani 1 1 d . . .
C35 C 0.55086(6) -0.48934(15) 0.71461(5) 0.0486(3) Uani 1 1 d . . .
H35 H 0.5205 -0.6123 0.6967 0.058 Uiso 1 1 calc R . .
C36 C 0.63954(6) -0.49095(16) 0.73674(5) 0.0528(3) Uani 1 1 d . . .
H36 H 0.6686 -0.6178 0.7337 0.063 Uiso 1 1 calc R . .
C37 C 0.40955(6) -0.30432(15) 0.69737(5) 0.0553(3) Uani 1 1 d . . .
H37A H 0.3884 -0.4272 0.6690 0.066 Uiso 1 1 calc R . .
H37B H 0.3881 -0.3156 0.7371 0.066 Uiso 1 1 calc R . .
C41 C 0.13292(6) 0.91448(15) 0.53062(5) 0.0456(3) Uani 1 1 d . . .
C42 C 0.14710(7) 0.84566(17) 0.47162(5) 0.0598(3) Uani 1 1 d . . .
H42 H 0.1680 0.7084 0.4689 0.072 Uiso 1 1 calc R . .
C43 C 0.13117(8) 0.97458(19) 0.41720(6) 0.0742(4) Uani 1 1 d . . .
H43 H 0.1400 0.9269 0.3768 0.089 Uiso 1 1 calc R . .
C44 C 0.10243(7) 1.17263(19) 0.42246(6) 0.0715(4) Uani 1 1 d . . .
F44 F 0.08974(6) 1.30271(13) 0.36980(4) 0.1130(3) Uani 1 1 d . . .
C45 C 0.08562(7) 1.24501(18) 0.47903(6) 0.0676(4) Uani 1 1 d . . .
H45 H 0.0638 1.3817 0.4809 0.081 Uiso 1 1 calc R . .
C46 C 0.10121(6) 1.11440(15) 0.53333(5) 0.0545(3) Uani 1 1 d . . .
H46 H 0.0901 1.1620 0.5730 0.065 Uiso 1 1 calc R . .
C47 C 0.15244(6) 0.77931(14) 0.58945(4) 0.0445(3) Uani 1 1 d . . .
N47 N 0.19656(5) 0.61060(12) 0.59205(4) 0.0495(2) Uani 1 1 d . . .
O47 O 0.20808(4) 0.50451(10) 0.65082(3) 0.0562(2) Uani 1 1 d . . .
H47 H 0.2506(6) 0.3834(15) 0.6487(5) 0.067 Uiso 1 1 d . . .
C48 C 0.12258(7) 0.83896(16) 0.64544(5) 0.0574(3) Uani 1 1 d . . .
N48 N 0.09860(7) 0.88476(17) 0.69001(5) 0.0932(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C12 1.3481(12) . ?
N11 C19 1.3900(12) . ?
N11 C37 1.4576(12) . ?
C12 N13 1.3165(12) . ?
C12 H12 0.9500 . ?
N13 C14 1.3996(12) . ?
C14 C19 1.3880(12) . ?
C14 C15 1.3922(13) . ?
C15 C16 1.3792(15) . ?
C15 H15 0.9500 . ?
C16 C17 1.4181(15) . ?
C16 C20 1.5109(15) . ?
C17 C18 1.3831(15) . ?
C17 C21 1.5207(17) . ?
C18 C19 1.3942(14) . ?
C18 H18 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
N31 C36 1.3321(12) . ?
N31 C32 1.3361(13) . ?
C32 C33 1.3794(13) . ?
C32 H32 0.9500 . ?
C33 C34 1.3800(13) . ?
C33 H33 0.9500 . ?
C34 C35 1.3818(13) . ?
C34 C37 1.5066(13) . ?
C35 C36 1.3803(13) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C41 C46 1.3880(14) . ?
C41 C42 1.3928(15) . ?
C41 C47 1.4711(13) . ?
C42 C43 1.3768(15) . ?
C42 H42 0.9500 . ?
C43 C44 1.3675(17) . ?
C43 H43 0.9500 . ?
C44 F44 1.3555(13) . ?
C44 C45 1.3708(17) . ?
C45 C46 1.3816(15) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 N47 1.2889(12) . ?
C47 C48 1.4406(15) . ?
N47 O47 1.3769(10) . ?
O47 H47 1.047(10) . ?
C48 N48 1.1456(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N11 C19 106.51(7) . . ?
C12 N11 C37 126.81(9) . . ?
C19 N11 C37 126.68(8) . . ?
N13 C12 N11 113.71(9) . . ?
N13 C12 H12 123.1 . . ?
N11 C12 H12 123.1 . . ?
C12 N13 C14 104.59(8) . . ?
C19 C14 C15 119.85(9) . . ?
C19 C14 N13 109.47(8) . . ?
C15 C14 N13 130.65(8) . . ?
C16 C15 C14 119.29(9) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 120.30(9) . . ?
C15 C16 C20 119.48(10) . . ?
C17 C16 C20 120.19(10) . . ?
C18 C17 C16 120.72(10) . . ?
C18 C17 C21 119.04(10) . . ?
C16 C17 C21 120.24(10) . . ?
C17 C18 C19 117.81(9) . . ?
C17 C18 H18 121.1 . . ?
C19 C18 H18 121.1 . . ?
C14 C19 N11 105.71(8) . . ?
C14 C19 C18 122.02(9) . . ?
N11 C19 C18 132.22(8) . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C36 N31 C32 115.85(8) . . ?
N31 C32 C33 124.18(9) . . ?
N31 C32 H32 117.9 . . ?
C33 C32 H32 117.9 . . ?
C32 C33 C34 119.36(9) . . ?
C32 C33 H33 120.3 . . ?
C34 C33 H33 120.3 . . ?
C33 C34 C35 117.06(8) . . ?
C33 C34 C37 122.21(9) . . ?
C35 C34 C37 120.68(8) . . ?
C36 C35 C34 119.65(9) . . ?
C36 C35 H35 120.2 . . ?
C34 C35 H35 120.2 . . ?
N31 C36 C35 123.90(9) . . ?
N31 C36 H36 118.1 . . ?
C35 C36 H36 118.1 . . ?
N11 C37 C34 113.06(8) . . ?
N11 C37 H37A 109.0 . . ?
C34 C37 H37A 109.0 . . ?
N11 C37 H37B 109.0 . . ?
C34 C37 H37B 109.0 . . ?
H37A C37 H37B 107.8 . . ?
C46 C41 C42 118.83(9) . . ?
C46 C41 C47 120.44(9) . . ?
C42 C41 C47 120.73(9) . . ?
C43 C42 C41 120.64(10) . . ?
C43 C42 H42 119.7 . . ?
C41 C42 H42 119.7 . . ?
C44 C43 C42 118.76(12) . . ?
C44 C43 H43 120.6 . . ?
C42 C43 H43 120.6 . . ?
F44 C44 C43 118.98(11) . . ?
F44 C44 C45 118.52(11) . . ?
C43 C44 C45 122.50(11) . . ?
C44 C45 C46 118.41(11) . . ?
C44 C45 H45 120.8 . . ?
C46 C45 H45 120.8 . . ?
C45 C46 C41 120.81(11) . . ?
C45 C46 H46 119.6 . . ?
C41 C46 H46 119.6 . . ?
N47 C47 C48 119.60(9) . . ?
N47 C47 C41 121.27(9) . . ?
C48 C47 C41 119.12(8) . . ?
C47 N47 O47 112.96(8) . . ?
N47 O47 H47 104.9(5) . . ?
N48 C48 C47 179.44(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C19 N11 C12 N13 -0.54(10) . . . . ?
C37 N11 C12 N13 179.49(8) . . . . ?
N11 C12 N13 C14 0.10(10) . . . . ?
C12 N13 C14 C19 0.39(9) . . . . ?
C12 N13 C14 C15 178.29(9) . . . . ?
C19 C14 C15 C16 0.73(13) . . . . ?
N13 C14 C15 C16 -176.99(9) . . . . ?
C14 C15 C16 C17 0.46(14) . . . . ?
C14 C15 C16 C20 178.21(9) . . . . ?
C15 C16 C17 C18 -1.30(15) . . . . ?
C20 C16 C17 C18 -179.03(9) . . . . ?
C15 C16 C17 C21 177.91(9) . . . . ?
C20 C16 C17 C21 0.18(15) . . . . ?
C16 C17 C18 C19 0.89(14) . . . . ?
C21 C17 C18 C19 -178.33(9) . . . . ?
C15 C14 C19 N11 -178.87(8) . . . . ?
N13 C14 C19 N11 -0.70(9) . . . . ?
C15 C14 C19 C18 -1.16(13) . . . . ?
N13 C14 C19 C18 177.01(8) . . . . ?
C12 N11 C19 C14 0.74(9) . . . . ?
C37 N11 C19 C14 -179.30(8) . . . . ?
C12 N11 C19 C18 -176.64(9) . . . . ?
C37 N11 C19 C18 3.32(15) . . . . ?
C17 C18 C19 C14 0.33(13) . . . . ?
C17 C18 C19 N11 177.35(9) . . . . ?
C36 N31 C32 C33 0.43(16) . . . . ?
N31 C32 C33 C34 -0.70(17) . . . . ?
C32 C33 C34 C35 0.39(15) . . . . ?
C32 C33 C34 C37 177.99(10) . . . . ?
C33 C34 C35 C36 0.13(15) . . . . ?
C37 C34 C35 C36 -177.52(9) . . . . ?
C32 N31 C36 C35 0.13(15) . . . . ?
C34 C35 C36 N31 -0.41(16) . . . . ?
C12 N11 C37 C34 -106.58(11) . . . . ?
C19 N11 C37 C34 73.46(11) . . . . ?
C33 C34 C37 N11 43.11(14) . . . . ?
C35 C34 C37 N11 -139.37(9) . . . . ?
C46 C41 C42 C43 0.94(15) . . . . ?
C47 C41 C42 C43 -178.08(9) . . . . ?
C41 C42 C43 C44 1.00(17) . . . . ?
C42 C43 C44 F44 177.54(10) . . . . ?
C42 C43 C44 C45 -2.65(18) . . . . ?
F44 C44 C45 C46 -177.96(9) . . . . ?
C43 C44 C45 C46 2.24(17) . . . . ?
C44 C45 C46 C41 -0.18(15) . . . . ?
C42 C41 C46 C45 -1.36(14) . . . . ?
C47 C41 C46 C45 177.66(9) . . . . ?
C46 C41 C47 N47 -166.74(9) . . . . ?
C42 C41 C47 N47 12.27(14) . . . . ?
C46 C41 C47 C48 12.36(13) . . . . ?
C42 C41 C47 C48 -168.63(9) . . . . ?
C48 C47 N47 O47 1.06(12) . . . . ?
C41 C47 N47 O47 -179.84(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O47 H47 N13 1.047(10) 1.596(10) 2.6407(10) 175.9(8) .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        30.50
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.034

#END


