# Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Raju Mondal'
_publ_contact_author_email       ICRM@IACS.RES.IN

_publ_section_title              
;
Construction of First Anion-Assisted Helix inside a Helix Network
;
loop_
_publ_author_name
'Raju Mondal'
'Tannistha Basu'

# Attachment 'CLO4.cif'

data_rm7
_database_code_depnum_ccdc_archive 'CCDC 742408'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H18 Cl2 N4 O8'
_chemical_formula_weight         405.19

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   14.7440(3)
_cell_length_b                   13.7417(3)
_cell_length_c                   16.8120(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3406.24(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9718
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      27.68

_exptl_crystal_description       Cube
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1680
_exptl_absorpt_coefficient_mu    0.430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.857938
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
'SADABS v.2.03 (Bruker, 2001), R(int)=0.0706 before correction'

_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  'Bruker APEX-2 CCD area detector'
_diffrn_measurement_method       '/w scans'
_diffrn_detector_area_resol_mean 8
_diffrn_standards_decay_%        0
_diffrn_reflns_number            47448
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         30.62
_reflns_number_total             5200
_reflns_number_gt                3863
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX-2'
_computing_cell_refinement       'Bruker APEX-2'
_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)+(0.0764P)²+2.6376P] 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         5200
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1478
_refine_ls_wR_factor_gt          0.1342
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
Cl2 Cl 0.23504(3) 0.46850(4) 0.14983(3) 0.02630(14) Uani 1 1 d . . .
N1 N 0.46187(12) 0.56247(12) 0.10793(10) 0.0218(3) Uani 1 1 d . . .
C2 C 0.57723(12) 0.65458(13) 0.14448(10) 0.0170(3) Uani 1 1 d . . .
C3 C 0.60998(13) 0.56471(14) 0.11950(11) 0.0198(4) Uani 1 1 d . . .
N3 N 0.57714(14) 0.97412(15) 0.08183(15) 0.0357(5) Uani 1 1 d . . .
C8 C 0.41156(13) 0.72341(15) 0.15408(12) 0.0233(4) Uani 1 1 d . . .
H8A H 0.3531 0.6967 0.1416 0.035 Uiso 1 1 calc R . .
H8B H 0.4218 0.7806 0.1225 0.035 Uiso 1 1 calc R . .
H8C H 0.4137 0.7403 0.2095 0.035 Uiso 1 1 calc R . .
C4 C 0.57689(14) 0.91541(15) 0.14559(13) 0.0265(4) Uani 1 1 d . . .
N2 N 0.53853(12) 0.51083(13) 0.09724(10) 0.0238(4) Uani 1 1 d . . .
C7 C 0.63145(13) 0.73972(14) 0.17331(12) 0.0198(4) Uani 1 1 d . . .
C5 C 0.61778(12) 0.82834(13) 0.12275(12) 0.0196(4) Uani 1 1 d . . .
O5 O 0.14406(11) 0.46853(13) 0.11801(11) 0.0388(4) Uani 1 1 d . . .
C9 C 0.70428(15) 0.52668(16) 0.11436(14) 0.0288(4) Uani 1 1 d . . .
H9A H 0.7032 0.4612 0.0944 0.043 Uiso 1 1 calc R . .
H9B H 0.7314 0.5274 0.1663 0.043 Uiso 1 1 calc R . .
H9C H 0.7391 0.5669 0.0791 0.043 Uiso 1 1 calc R . .
C6 C 0.64268(13) 0.84025(15) 0.04329(12) 0.0247(4) Uani 1 1 d . . .
C1 C 0.48281(12) 0.65035(14) 0.13655(11) 0.0182(4) Uani 1 1 d . . .
O6 O 0.29733(12) 0.47038(15) 0.08329(11) 0.0448(5) Uani 1 1 d . . .
N4 N 0.61717(13) 0.92929(15) 0.02085(13) 0.0338(5) Uani 1 1 d . . .
C11 C 0.69015(15) 0.7733(2) -0.01217(13) 0.0343(5) Uani 1 1 d . . .
H11A H 0.6968 0.8042 -0.0630 0.051 Uiso 1 1 calc R . .
H11B H 0.6554 0.7147 -0.0181 0.051 Uiso 1 1 calc R . .
H11C H 0.7489 0.7577 0.0088 0.051 Uiso 1 1 calc R . .
O7 O 0.24934(16) 0.55447(15) 0.19545(12) 0.0541(6) Uani 1 1 d . . .
O8 O 0.24743(14) 0.38461(15) 0.19700(14) 0.0582(6) Uani 1 1 d . . .
C10 C 0.53856(18) 0.94633(19) 0.22330(16) 0.0414(6) Uani 1 1 d . . .
H10A H 0.5153 1.0114 0.2188 0.062 Uiso 1 1 calc R . .
H10B H 0.5852 0.9446 0.2631 0.062 Uiso 1 1 calc R . .
H10C H 0.4904 0.9030 0.2382 0.062 Uiso 1 1 calc R . .
Cl1 Cl 0.05761(3) 0.24081(3) 0.40529(3) 0.02306(13) Uani 1 1 d . . .
O1 O 0.01124(14) 0.31780(12) 0.44753(12) 0.0427(5) Uani 1 1 d . . .
O2 O 0.13180(13) 0.28053(15) 0.36263(12) 0.0458(5) Uani 1 1 d . . .
O3 O -0.00414(15) 0.19211(17) 0.35333(12) 0.0545(6) Uani 1 1 d . . .
O4 O 0.08795(16) 0.17156(13) 0.46363(12) 0.0495(5) Uani 1 1 d . . .
H7A H 0.6174(19) 0.7516(19) 0.2271(17) 0.035(7) Uiso 1 1 d . . .
H7B H 0.6967(18) 0.7232(18) 0.1726(15) 0.027(6) Uiso 1 1 d . . .
H222 H 0.5372(19) 0.454(2) 0.0866(16) 0.031(7) Uiso 1 1 d . . .
H111 H 0.4112(18) 0.5358(18) 0.0981(15) 0.027(7) Uiso 1 1 d . . .
H444 H 0.626(2) 0.960(2) -0.020(2) 0.058(10) Uiso 1 1 d . . .
H333 H 0.567(2) 1.024(2) 0.075(2) 0.046(9) Uiso 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
Cl2 O8 1.4112(19) . ?
Cl2 O7 1.4242(19) . ?
Cl2 O5 1.4441(17) . ?
Cl2 O6 1.4477(18) . ?
N1 C1 1.336(2) . ?
N1 N2 1.347(2) . ?
N1 H111 0.85(3) . ?
C2 C3 1.391(3) . ?
C2 C1 1.400(2) . ?
C2 C7 1.498(3) . ?
C3 N2 1.341(3) . ?
C3 C9 1.488(3) . ?
N3 N4 1.334(3) . ?
N3 C4 1.342(3) . ?
N3 H333 0.71(3) . ?
C8 C1 1.483(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C4 C5 1.394(3) . ?
C4 C10 1.486(3) . ?
N2 H222 0.80(3) . ?
C7 C5 1.499(3) . ?
C7 H7A 0.94(3) . ?
C7 H7B 0.99(3) . ?
C5 C6 1.395(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C6 N4 1.334(3) . ?
C6 C11 1.485(3) . ?
N4 H444 0.82(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
Cl1 O2 1.4173(18) . ?
Cl1 O3 1.4283(19) . ?
Cl1 O4 1.4379(18) . ?
Cl1 O1 1.4461(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
O8 Cl2 O7 110.85(14) . . ?
O8 Cl2 O5 109.19(11) . . ?
O7 Cl2 O5 109.68(13) . . ?
O8 Cl2 O6 111.51(15) . . ?
O7 Cl2 O6 107.90(11) . . ?
O5 Cl2 O6 107.64(11) . . ?
C1 N1 N2 109.29(16) . . ?
C1 N1 H111 131.6(17) . . ?
N2 N1 H111 119.1(17) . . ?
C3 C2 C1 106.24(17) . . ?
C3 C2 C7 127.30(17) . . ?
C1 C2 C7 126.46(17) . . ?
N2 C3 C2 107.56(17) . . ?
N2 C3 C9 121.60(18) . . ?
C2 C3 C9 130.83(19) . . ?
N4 N3 C4 109.7(2) . . ?
N4 N3 H333 114(3) . . ?
C4 N3 H333 135(3) . . ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N3 C4 C5 107.2(2) . . ?
N3 C4 C10 122.1(2) . . ?
C5 C4 C10 130.7(2) . . ?
C3 N2 N1 109.34(16) . . ?
C3 N2 H222 128(2) . . ?
N1 N2 H222 122(2) . . ?
C2 C7 C5 112.30(16) . . ?
C2 C7 H7A 109.2(16) . . ?
C5 C7 H7A 112.0(16) . . ?
C2 C7 H7B 109.6(14) . . ?
C5 C7 H7B 108.1(15) . . ?
H7A C7 H7B 105(2) . . ?
C4 C5 C6 106.08(18) . . ?
C4 C5 C7 126.84(19) . . ?
C6 C5 C7 127.08(18) . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C6 C5 107.7(2) . . ?
N4 C6 C11 121.6(2) . . ?
C5 C6 C11 130.7(2) . . ?
N1 C1 C2 107.56(17) . . ?
N1 C1 C8 121.32(17) . . ?
C2 C1 C8 131.12(18) . . ?
N3 N4 C6 109.3(2) . . ?
N3 N4 H444 119(2) . . ?
C6 N4 H444 132(2) . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 Cl1 O3 111.27(13) . . ?
O2 Cl1 O4 111.10(13) . . ?
O3 Cl1 O4 107.78(13) . . ?
O2 Cl1 O1 109.37(11) . . ?
O3 Cl1 O1 109.98(13) . . ?
O4 Cl1 O1 107.24(12) . . ?

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
N1 H111 O6 0.85(3) 1.92(3) 2.767(2) 176(3) .
N2 H222 O1 0.80(3) 1.99(3) 2.786(3) 169(3) 6_656
N3 H333 O4 0.71(3) 2.15(3) 2.823(3) 159(4) 6_666
N4 H444 O5 0.82(3) 1.94(4) 2.753(3) 178(4) 4_565

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        30.62
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.999
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.079

# Attachment 'FORM-A.cif'

data_09tba012_0m
_database_code_depnum_ccdc_archive 'CCDC 742409'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H16 N4'
_chemical_formula_weight         204.28

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'

_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                   7.2653(2)
_cell_length_b                   8.4142(2)
_cell_length_c                   9.8774(2)
_cell_angle_alpha                99.3630(10)
_cell_angle_beta                 101.8060(10)
_cell_angle_gamma                106.7770(10)
_cell_volume                     549.82(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2134
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      34.86

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             220
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.853349
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
'SADABS v.2.03 (Bruker, 2001), R(int)=0.0305 before correction'

_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  'Bruker APEX-2 CCD area detector'
_diffrn_measurement_method       '/w scans'
_diffrn_detector_area_resol_mean 8
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10025
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         33.50
_reflns_number_total             4223
_reflns_number_gt                3265
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX-2'
_computing_cell_refinement       'Bruker APEX-2'
_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)+(0.0930P)²+0.0635P] 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         4223
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1629
_refine_ls_wR_factor_gt          0.1535
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
N1 N 0.06916(14) 0.31651(12) 0.30607(11) 0.0228(2) Uani 1 1 d . . .
C1 C 0.21535(15) 0.32471(14) 0.24053(12) 0.0208(2) Uani 1 1 d . . .
C5 C 0.59289(15) 0.71265(14) 0.21244(12) 0.0208(2) Uani 1 1 d . . .
N2 N 0.11913(15) 0.46730(12) 0.40238(11) 0.0242(2) Uani 1 1 d . . .
C2 C 0.36301(15) 0.48356(13) 0.29506(12) 0.0205(2) Uani 1 1 d . . .
N3 N 0.74940(14) 0.98006(13) 0.20615(12) 0.0265(2) Uani 1 1 d . . .
C4 C 0.77310(15) 0.84812(14) 0.25907(12) 0.0216(2) Uani 1 1 d . . .
C3 C 0.29687(17) 0.56970(14) 0.39765(12) 0.0228(2) Uani 1 1 d . . .
C6 C 0.46231(16) 0.77185(17) 0.12691(13) 0.0254(2) Uani 1 1 d . . .
N4 N 0.55875(15) 0.93349(15) 0.12557(13) 0.0299(2) Uani 1 1 d . . .
H444 H 0.5081 0.9971 0.0810 0.036 Uiso 0.50 1 calc PR . .
C7 C 0.55208(18) 0.54247(16) 0.24992(18) 0.0316(3) Uani 1 1 d . . .
C10 C 0.97033(18) 0.85324(18) 0.34556(14) 0.0299(3) Uani 1 1 d . . .
C9 C 0.3945(2) 0.74471(16) 0.49286(15) 0.0316(3) Uani 1 1 d . . .
C8 C 0.2057(2) 0.17819(17) 0.12859(15) 0.0321(3) Uani 1 1 d . . .
C11 C 0.24948(18) 0.6835(2) 0.04415(17) 0.0376(3) Uani 1 1 d . . .
H8C H 0.090(3) 0.084(3) 0.115(2) 0.048(5) Uiso 1 1 d . . .
H9C H 0.532(4) 0.765(3) 0.540(3) 0.066(7) Uiso 1 1 d . . .
H7B H 0.665(3) 0.547(3) 0.319(2) 0.051(6) Uiso 1 1 d . . .
H9B H 0.326(3) 0.763(3) 0.563(2) 0.048(5) Uiso 1 1 d . . .
H7A H 0.545(3) 0.448(3) 0.163(2) 0.058(6) Uiso 1 1 d . . .
H9A H 0.395(3) 0.832(3) 0.436(2) 0.053(6) Uiso 1 1 d . . .
H10C H 0.958(3) 0.823(3) 0.440(2) 0.043(5) Uiso 1 1 d . . .
H10B H 1.023(3) 0.775(3) 0.290(2) 0.042(5) Uiso 1 1 d . . .
H8B H 0.320(4) 0.135(3) 0.161(2) 0.060(6) Uiso 1 1 d . . .
H10A H 1.071(3) 0.967(3) 0.368(2) 0.055(6) Uiso 1 1 d . . .
H8A H 0.210(4) 0.209(3) 0.033(3) 0.067(7) Uiso 1 1 d . . .
H11C H 0.221(4) 0.564(3) -0.001(3) 0.062(7) Uiso 1 1 d . . .
H11B H 0.160(4) 0.667(3) 0.105(3) 0.060(6) Uiso 1 1 d . . .
H11A H 0.212(4) 0.741(4) -0.017(3) 0.085(9) Uiso 1 1 d . . .
H111 H -0.046(4) 0.238(4) 0.283(3) 0.017(6) Uiso 0.50 1 d P . .
H222 H 0.055(4) 0.492(4) 0.458(3) 0.017(6) Uiso 0.50 1 d P . .
H333 H 0.836(5) 1.085(4) 0.239(3) 0.019(7) Uiso 0.50 1 d P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.3438(14) . ?
N1 N2 1.3589(14) . ?
N1 H111 0.86(3) . ?
C1 C2 1.3888(14) . ?
C1 C8 1.4908(17) . ?
C5 C6 1.3941(16) . ?
C5 C4 1.3952(14) . ?
C5 C7 1.4992(16) . ?
N2 C3 1.3445(15) . ?
N2 H222 0.83(3) . ?
C2 C3 1.3944(16) . ?
C2 C7 1.5037(15) . ?
N3 C4 1.3407(15) . ?
N3 N4 1.3564(14) . ?
N3 H333 0.89(3) . ?
C4 C10 1.4955(16) . ?
C3 C9 1.4931(16) . ?
C6 N4 1.3418(17) . ?
C6 C11 1.4944(17) . ?
N4 H444 0.8600 . ?
C7 H7B 0.94(2) . ?
C7 H7A 1.05(2) . ?
C10 H10C 1.02(2) . ?
C10 H10B 0.99(2) . ?
C10 H10A 0.98(2) . ?
C9 H9C 0.96(2) . ?
C9 H9B 0.95(2) . ?
C9 H9A 1.00(2) . ?
C8 H8C 0.94(2) . ?
C8 H8B 1.02(2) . ?
C8 H8A 1.02(3) . ?
C11 H11C 0.97(3) . ?
C11 H11B 0.97(2) . ?
C11 H11A 0.88(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 108.34(9) . . ?
C1 N1 H111 126.7(19) . . ?
N2 N1 H111 124.2(19) . . ?
N1 C1 C2 109.13(10) . . ?
N1 C1 C8 121.59(10) . . ?
C2 C1 C8 129.28(10) . . ?
C6 C5 C4 105.03(10) . . ?
C6 C5 C7 128.48(10) . . ?
C4 C5 C7 126.49(11) . . ?
C3 N2 N1 108.60(10) . . ?
C3 N2 H222 125(2) . . ?
N1 N2 H222 127(2) . . ?
C1 C2 C3 105.17(9) . . ?
C1 C2 C7 125.49(11) . . ?
C3 C2 C7 129.34(10) . . ?
C4 N3 N4 108.54(9) . . ?
C4 N3 H333 122(2) . . ?
N4 N3 H333 127(2) . . ?
N3 C4 C5 108.91(10) . . ?
N3 C4 C10 122.24(10) . . ?
C5 C4 C10 128.73(11) . . ?
N2 C3 C2 108.76(10) . . ?
N2 C3 C9 121.66(11) . . ?
C2 C3 C9 129.59(11) . . ?
N4 C6 C5 108.78(10) . . ?
N4 C6 C11 121.04(12) . . ?
C5 C6 C11 130.18(12) . . ?
C6 N4 N3 108.72(10) . . ?
C6 N4 H444 125.6 . . ?
N3 N4 H444 125.6 . . ?
C5 C7 C2 114.55(10) . . ?
C5 C7 H7B 107.7(13) . . ?
C2 C7 H7B 112.5(13) . . ?
C5 C7 H7A 110.0(13) . . ?
C2 C7 H7A 108.2(13) . . ?
H7B C7 H7A 103.4(18) . . ?
C4 C10 H10C 110.5(11) . . ?
C4 C10 H10B 109.8(11) . . ?
H10C C10 H10B 111.7(15) . . ?
C4 C10 H10A 112.2(13) . . ?
H10C C10 H10A 107.1(17) . . ?
H10B C10 H10A 105.5(17) . . ?
C3 C9 H9C 112.3(15) . . ?
C3 C9 H9B 111.0(13) . . ?
H9C C9 H9B 108.5(18) . . ?
C3 C9 H9A 110.1(13) . . ?
H9C C9 H9A 106.2(19) . . ?
H9B C9 H9A 108.5(18) . . ?
C1 C8 H8C 111.2(13) . . ?
C1 C8 H8B 109.8(13) . . ?
H8C C8 H8B 104.7(17) . . ?
C1 C8 H8A 112.8(14) . . ?
H8C C8 H8A 108.8(18) . . ?
H8B C8 H8A 109.2(18) . . ?
C6 C11 H11C 113.2(14) . . ?
C6 C11 H11B 112.6(14) . . ?
H11C C11 H11B 98.5(19) . . ?
C6 C11 H11A 110.8(19) . . ?
H11C C11 H11A 112(2) . . ?
H11B C11 H11A 109(2) . . ?

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
N1 H111 N3 0.86(3) 2.15(3) 2.9566(14) 155(3) 1_445
N2 H222 N2 0.83(3) 2.10(3) 2.931(2) 175(3) 2_566
N3 H333 N1 0.89(3) 2.08(3) 2.9566(14) 171(3) 1_665
N4 H444 N4 0.86 2.21 2.954(2) 144.5 2_675

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        33.50
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.056

# Attachment 'FORM-B.cif'

data_09tba028_0m
_database_code_depnum_ccdc_archive 'CCDC 742410'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H16 N4'
_chemical_formula_weight         204.28

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   8.2313(3)
_cell_length_b                   16.1062(7)
_cell_length_c                   17.0904(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2265.76(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4142
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      25.61

_exptl_crystal_description       Cube
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.882810
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
'SADABS v.2.03 (Bruker, 2001), R(int)=0.0483 before correction'

_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  'Bruker APEX-2 CCD area detector'
_diffrn_measurement_method       '/w scans'
_diffrn_detector_area_resol_mean 8
_diffrn_standards_decay_%        0
_diffrn_reflns_number            25866
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         25.52
_reflns_number_total             2106
_reflns_number_gt                1717
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX-2'
_computing_cell_refinement       'Bruker APEX-2'
_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)+(0.0706P)²+0.7192P] 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         2106
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1337
_refine_ls_wR_factor_gt          0.1264
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_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
N1 N -0.0067(2) 0.89347(8) 0.33961(9) 0.0322(4) Uani 1 1 d . . .
H1A H -0.0299 0.8458 0.3171 0.039 Uiso 1 1 calc R . .
N2 N 0.1413(2) 0.91485(9) 0.36829(9) 0.0323(4) Uani 1 1 d . . .
C5 C -0.0269(2) 1.17709(9) 0.37412(10) 0.0245(4) Uani 1 1 d . . .
N3 N 0.1026(2) 1.29554(9) 0.35332(9) 0.0351(4) Uani 1 1 d . . .
H3A H 0.1577 1.3416 0.3614 0.042 Uiso 1 1 calc R . .
C2 C -0.0303(2) 1.02019(10) 0.38807(9) 0.0242(4) Uani 1 1 d . . .
N4 N 0.0489(2) 1.26874(9) 0.28250(9) 0.0358(4) Uani 1 1 d . . .
C1 C -0.1120(2) 0.95571(10) 0.35070(10) 0.0273(4) Uani 1 1 d . . .
C6 C -0.0304(2) 1.19723(10) 0.29444(10) 0.0281(4) Uani 1 1 d . . .
C3 C 0.1280(2) 0.99180(10) 0.39819(9) 0.0268(4) Uani 1 1 d . . .
C7 C -0.1007(2) 1.10230(10) 0.41306(11) 0.0276(4) Uani 1 1 d . . .
C4 C 0.0592(2) 1.24123(10) 0.40918(10) 0.0295(4) Uani 1 1 d . . .
C11 C -0.1020(3) 1.15069(13) 0.22756(12) 0.0376(5) Uani 1 1 d . . .
C9 C 0.2683(3) 1.03219(13) 0.43803(11) 0.0348(5) Uani 1 1 d . . .
C8 C -0.2847(3) 0.94843(14) 0.32571(13) 0.0390(5) Uani 1 1 d . . .
C10 C 0.1029(3) 1.25511(14) 0.49287(13) 0.0440(6) Uani 1 1 d . . .
H7B H -0.082(2) 1.1063(12) 0.4654(13) 0.035(5) Uiso 1 1 d . . .
H7A H -0.225(3) 1.1018(12) 0.3999(11) 0.038(5) Uiso 1 1 d . . .
H11C H -0.048(3) 1.0993(17) 0.2209(15) 0.067(8) Uiso 1 1 d . . .
H9C H 0.244(3) 1.0461(15) 0.4956(16) 0.072(8) Uiso 1 1 d . . .
H9B H 0.291(3) 1.0866(17) 0.4169(15) 0.063(7) Uiso 1 1 d . . .
H8C H -0.306(3) 0.9801(17) 0.2807(17) 0.071(8) Uiso 1 1 d . . .
H11B H -0.102(4) 1.1857(19) 0.1826(18) 0.084(9) Uiso 1 1 d . . .
H11A H -0.215(4) 1.1347(16) 0.2384(15) 0.072(8) Uiso 1 1 d . . .
H8B H -0.364(4) 0.9713(19) 0.3622(19) 0.092(10) Uiso 1 1 d . . .
H8A H -0.303(3) 0.8925(19) 0.3149(16) 0.077(9) Uiso 1 1 d . . .
H9A H 0.363(4) 0.9972(18) 0.4367(15) 0.073(8) Uiso 1 1 d . . .
H10B H 0.082(4) 1.305(2) 0.5113(19) 0.102(11) Uiso 1 1 d . . .
H10A H 0.039(5) 1.219(2) 0.534(2) 0.129(13) Uiso 1 1 d . . .
H10C H 0.201(5) 1.234(2) 0.504(2) 0.113(13) Uiso 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
N1 C1 1.339(2) . ?
N1 N2 1.357(2) . ?
N1 H1A 0.8800 . ?
N2 C3 1.345(2) . ?
C5 C4 1.389(2) . ?
C5 C6 1.400(2) . ?
C5 C7 1.504(2) . ?
N3 C4 1.343(2) . ?
N3 N4 1.359(2) . ?
N3 H3A 0.8800 . ?
C2 C1 1.392(2) . ?
C2 C3 1.392(3) . ?
C2 C7 1.506(2) . ?
N4 C6 1.339(2) . ?
C1 C8 1.489(3) . ?
C6 C11 1.488(3) . ?
C3 C9 1.490(3) . ?
C7 H7B 0.91(2) . ?
C7 H7A 1.05(2) . ?
C4 C10 1.492(3) . ?
C11 H11C 0.95(3) . ?
C11 H11B 0.95(3) . ?
C11 H11A 0.99(3) . ?
C9 H9C 1.03(3) . ?
C9 H9B 0.96(3) . ?
C9 H9A 0.96(3) . ?
C8 H8C 0.94(3) . ?
C8 H8B 0.98(3) . ?
C8 H8A 0.93(3) . ?
C10 H10B 0.88(4) . ?
C10 H10A 1.05(4) . ?
C10 H10C 0.89(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 109.87(14) . . ?
C1 N1 H1A 125.1 . . ?
N2 N1 H1A 125.1 . . ?
C3 N2 N1 107.35(14) . . ?
C4 C5 C6 104.94(14) . . ?
C4 C5 C7 127.65(16) . . ?
C6 C5 C7 127.42(15) . . ?
C4 N3 N4 109.85(14) . . ?
C4 N3 H3A 125.1 . . ?
N4 N3 H3A 125.1 . . ?
C1 C2 C3 105.32(15) . . ?
C1 C2 C7 126.85(16) . . ?
C3 C2 C7 127.83(16) . . ?
C6 N4 N3 107.22(14) . . ?
N1 C1 C2 108.11(16) . . ?
N1 C1 C8 121.24(16) . . ?
C2 C1 C8 130.65(17) . . ?
N4 C6 C5 109.72(15) . . ?
N4 C6 C11 120.60(16) . . ?
C5 C6 C11 129.66(16) . . ?
N2 C3 C2 109.35(16) . . ?
N2 C3 C9 120.88(16) . . ?
C2 C3 C9 129.71(16) . . ?
C5 C7 C2 115.01(14) . . ?
C5 C7 H7B 108.2(12) . . ?
C2 C7 H7B 106.1(12) . . ?
C5 C7 H7A 107.8(10) . . ?
C2 C7 H7A 107.9(11) . . ?
H7B C7 H7A 111.9(16) . . ?
N3 C4 C5 108.27(15) . . ?
N3 C4 C10 121.32(17) . . ?
C5 C4 C10 130.41(17) . . ?
C6 C11 H11C 110.2(16) . . ?
C6 C11 H11B 108.7(18) . . ?
H11C C11 H11B 115(2) . . ?
C6 C11 H11A 111.3(15) . . ?
H11C C11 H11A 104(2) . . ?
H11B C11 H11A 108(2) . . ?
C3 C9 H9C 112.3(16) . . ?
C3 C9 H9B 112.0(15) . . ?
H9C C9 H9B 101.3(19) . . ?
C3 C9 H9A 111.2(16) . . ?
H9C C9 H9A 108(2) . . ?
H9B C9 H9A 112(2) . . ?
C1 C8 H8C 111.6(16) . . ?
C1 C8 H8B 115.3(19) . . ?
H8C C8 H8B 101(2) . . ?
C1 C8 H8A 106.9(18) . . ?
H8C C8 H8A 109(2) . . ?
H8B C8 H8A 112(3) . . ?
C4 C10 H10B 116(2) . . ?
C4 C10 H10A 116(2) . . ?
H10B C10 H10A 100(3) . . ?
C4 C10 H10C 111(2) . . ?
H10B C10 H10C 117(3) . . ?
H10A C10 H10C 96(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C3 0.27(18) . . . . ?
C4 N3 N4 C6 0.6(2) . . . . ?
N2 N1 C1 C2 -0.07(19) . . . . ?
N2 N1 C1 C8 -179.11(16) . . . . ?
C3 C2 C1 N1 -0.14(18) . . . . ?
C7 C2 C1 N1 -179.24(15) . . . . ?
C3 C2 C1 C8 178.78(18) . . . . ?
C7 C2 C1 C8 -0.3(3) . . . . ?
N3 N4 C6 C5 -0.4(2) . . . . ?
N3 N4 C6 C11 -178.81(17) . . . . ?
C4 C5 C6 N4 0.1(2) . . . . ?
C7 C5 C6 N4 -179.93(16) . . . . ?
C4 C5 C6 C11 178.3(2) . . . . ?
C7 C5 C6 C11 -1.7(3) . . . . ?
N1 N2 C3 C2 -0.35(18) . . . . ?
N1 N2 C3 C9 177.03(15) . . . . ?
C1 C2 C3 N2 0.31(18) . . . . ?
C7 C2 C3 N2 179.39(15) . . . . ?
C1 C2 C3 C9 -176.77(17) . . . . ?
C7 C2 C3 C9 2.3(3) . . . . ?
C4 C5 C7 C2 -116.6(2) . . . . ?
C6 C5 C7 C2 63.5(2) . . . . ?
C1 C2 C7 C5 -117.58(19) . . . . ?
C3 C2 C7 C5 63.5(2) . . . . ?
N4 N3 C4 C5 -0.5(2) . . . . ?
N4 N3 C4 C10 179.88(19) . . . . ?
C6 C5 C4 N3 0.23(19) . . . . ?
C7 C5 C4 N3 -179.71(16) . . . . ?
C6 C5 C4 C10 179.8(2) . . . . ?
C7 C5 C4 C10 -0.1(3) . . . . ?

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
N1 H1A N4 0.88 2.11 2.917(2) 151.8 3_545
N3 H3A N2 0.88 2.04 2.864(2) 156.4 8_665

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.52
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.043

# Attachment 'TFA.cif'

data_rm16
_database_code_depnum_ccdc_archive 'CCDC 742411'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H18 F6 N4 O4'
_chemical_formula_weight         432.33

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   15.3698(9)
_cell_length_b                   13.6543(8)
_cell_length_c                   18.7565(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3936.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4065
_cell_measurement_theta_min      2.13
_cell_measurement_theta_max      25.1

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1776
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.833942
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
'SADABS v.2.03 (Bruker, 2001), R(int)=0.0706 before correction'

_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  'Bruker APEX-2 CCD area detector'
_diffrn_measurement_method       '/w scans'
_diffrn_detector_area_resol_mean 8
_diffrn_standards_decay_%        0
_diffrn_reflns_number            52216
_diffrn_reflns_av_R_equivalents  0.0873
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         25.53
_reflns_number_total             3638
_reflns_number_gt                2734
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX-2'
_computing_cell_refinement       'Bruker APEX-2'
_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)+(0.0851P)²+4.8529P] 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         3638
_refine_ls_number_parameters     322
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.1714
_refine_ls_wR_factor_gt          0.1563
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
N1 N 0.03877(15) 0.51306(17) 0.09380(13) 0.0272(5) Uani 1 1 d . . .
N2 N -0.03599(16) 0.56294(17) 0.09934(12) 0.0252(5) Uani 1 1 d . . .
O1 O 0.30348(13) 0.99569(16) -0.06387(11) 0.0361(5) Uani 1 1 d . . .
O2 O 0.16720(13) 1.03237(17) -0.09487(11) 0.0407(6) Uani 1 1 d . . .
N3 N 0.07532(15) 0.98395(18) 0.07441(12) 0.0265(5) Uani 1 1 d . . .
O3 O 0.03610(15) 0.16783(14) 0.03933(11) 0.0387(6) Uani 1 1 d . . .
N4 N 0.12291(15) 0.93814(17) 0.02445(13) 0.0267(5) Uani 1 1 d . . .
F4 F 0.13286(15) 0.17862(17) 0.15924(12) 0.0628(7) Uani 1 1 d . . .
C2 C 0.06956(17) 0.66044(18) 0.13482(14) 0.0224(6) Uani 1 1 d . . .
F1 F 0.30580(16) 0.9985(2) -0.21752(11) 0.0697(7) Uani 1 1 d . . .
O4 O 0.02977(16) 0.33089(14) 0.04389(11) 0.0414(6) Uani 1 1 d . . .
C3 C -0.01996(17) 0.65305(19) 0.12328(13) 0.0232(6) Uani 1 1 d . . .
C5 C 0.10912(17) 0.83790(19) 0.11602(14) 0.0235(6) Uani 1 1 d . . .
C4 C 0.06604(17) 0.92471(19) 0.13107(14) 0.0245(6) Uani 1 1 d . . .
F5 F 0.0965(2) 0.32873(15) 0.17339(12) 0.0841(10) Uani 1 1 d . . .
F2 F 0.22242(17) 1.1202(3) -0.21108(14) 0.1016(12) Uani 1 1 d . . .
C10 C 0.0147(2) 0.9567(2) 0.19435(16) 0.0313(7) Uani 1 1 d . . .
F3 F 0.35225(18) 1.12491(19) -0.16562(13) 0.0757(8) Uani 1 1 d . . .
F6 F 0.00602(19) 0.2160(2) 0.18838(12) 0.0781(8) Uani 1 1 d . . .
C13 C 0.2467(2) 1.0298(2) -0.10345(15) 0.0301(7) Uani 1 1 d . . .
C1 C 0.10453(18) 0.5703(2) 0.11561(14) 0.0253(6) Uani 1 1 d . . .
C6 C 0.14393(17) 0.8490(2) 0.04749(14) 0.0254(6) Uani 1 1 d . . .
C9 C -0.0905(2) 0.7258(2) 0.13192(18) 0.0305(7) Uani 1 1 d . . .
C15 C 0.04369(19) 0.2485(2) 0.06850(15) 0.0278(6) Uani 1 1 d . . .
C11 C 0.1938(3) 0.7795(3) 0.00249(19) 0.0381(8) Uani 1 1 d . . .
C14 C 0.0728(2) 0.2447(2) 0.14673(16) 0.0352(7) Uani 1 1 d . . .
C7 C 0.11751(19) 0.7487(2) 0.16254(15) 0.0261(6) Uani 1 1 d . . .
C8 C 0.19601(19) 0.5339(2) 0.11549(17) 0.0339(7) Uani 1 1 d . . .
H8A H 0.1972 0.4674 0.0988 0.051 Uiso 1 1 calc R . .
H8B H 0.2191 0.5366 0.1630 0.051 Uiso 1 1 calc R . .
H8C H 0.2307 0.5741 0.0846 0.051 Uiso 1 1 calc R . .
C12 C 0.2805(2) 1.0716(3) -0.17448(18) 0.0454(9) Uani 1 1 d . . .
H7A H 0.099(2) 0.765(2) 0.2104(19) 0.038(9) Uiso 1 1 d . . .
H7B H 0.179(2) 0.728(2) 0.1669(17) 0.035(8) Uiso 1 1 d . . .
H9A H -0.084(2) 0.774(3) 0.095(2) 0.050(10) Uiso 1 1 d . . .
H333 H 0.061(2) 1.047(2) 0.0665(16) 0.029(8) Uiso 1 1 d . . .
H9B H -0.088(2) 0.761(3) 0.174(2) 0.049(10) Uiso 1 1 d . . .
H9C H -0.147(2) 0.695(3) 0.1327(17) 0.040(9) Uiso 1 1 d . . .
H10A H 0.022(2) 0.910(3) 0.233(2) 0.053(10) Uiso 1 1 d . . .
H111 H 0.039(2) 0.446(3) 0.0784(18) 0.040(9) Uiso 1 1 d . . .
H222 H -0.084(2) 0.539(3) 0.0861(18) 0.038(10) Uiso 1 1 d . . .
H11A H 0.238(3) 0.754(3) 0.028(2) 0.058(12) Uiso 1 1 d . . .
H11B H 0.214(3) 0.814(3) -0.036(2) 0.071(13) Uiso 1 1 d . . .
H10B H -0.041(3) 0.958(3) 0.185(2) 0.071(14) Uiso 1 1 d . . .
H10C H 0.037(3) 1.022(4) 0.212(3) 0.091(16) Uiso 1 1 d . . .
H444 H 0.139(3) 0.965(3) -0.016(2) 0.064(12) Uiso 1 1 d . . .
H11C H 0.158(3) 0.725(4) -0.012(3) 0.080(14) Uiso 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
N1 N2 1.340(3) . ?
N1 C1 1.341(4) . ?
N1 H111 0.97(4) . ?
N2 C3 1.333(4) . ?
N2 H222 0.84(4) . ?
O1 C13 1.236(4) . ?
O2 C13 1.234(4) . ?
N3 N4 1.343(3) . ?
N3 C4 1.343(4) . ?
N3 H333 0.90(3) . ?
O3 C15 1.236(3) . ?
N4 C6 1.331(4) . ?
N4 H444 0.88(4) . ?
F4 C14 1.313(4) . ?
C2 C1 1.391(4) . ?
C2 C3 1.397(4) . ?
C2 C7 1.505(4) . ?
F1 C12 1.341(4) . ?
O4 C15 1.234(3) . ?
C3 C9 1.480(4) . ?
C5 C4 1.387(4) . ?
C5 C6 1.401(4) . ?
C5 C7 1.504(4) . ?
C4 C10 1.490(4) . ?
F5 C14 1.303(4) . ?
F2 C12 1.307(4) . ?
C10 H10A 0.98(4) . ?
C10 H10B 0.88(5) . ?
C10 H10C 1.02(5) . ?
F3 C12 1.332(4) . ?
F6 C14 1.348(4) . ?
C13 C12 1.539(4) . ?
C1 C8 1.491(4) . ?
C6 C11 1.484(4) . ?
C9 H9A 0.96(4) . ?
C9 H9B 0.93(4) . ?
C9 H9C 0.96(4) . ?
C15 C14 1.535(4) . ?
C11 H11A 0.90(4) . ?
C11 H11B 0.92(5) . ?
C11 H11C 0.95(5) . ?
C7 H7A 0.97(3) . ?
C7 H7B 0.99(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

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
N2 N1 C1 109.1(2) . . ?
N2 N1 H111 121(2) . . ?
C1 N1 H111 130(2) . . ?
C3 N2 N1 109.7(2) . . ?
C3 N2 H222 128(2) . . ?
N1 N2 H222 122(2) . . ?
N4 N3 C4 109.2(2) . . ?
N4 N3 H333 118(2) . . ?
C4 N3 H333 133(2) . . ?
C6 N4 N3 109.4(2) . . ?
C6 N4 H444 126(3) . . ?
N3 N4 H444 124(3) . . ?
C1 C2 C3 106.1(2) . . ?
C1 C2 C7 127.5(2) . . ?
C3 C2 C7 126.4(2) . . ?
N2 C3 C2 107.5(2) . . ?
N2 C3 C9 121.4(3) . . ?
C2 C3 C9 131.0(3) . . ?
C4 C5 C6 106.0(2) . . ?
C4 C5 C7 128.0(3) . . ?
C6 C5 C7 126.0(2) . . ?
N3 C4 C5 107.6(2) . . ?
N3 C4 C10 120.7(3) . . ?
C5 C4 C10 131.7(3) . . ?
C4 C10 H10A 110(2) . . ?
C4 C10 H10B 112(3) . . ?
H10A C10 H10B 106(4) . . ?
C4 C10 H10C 110(3) . . ?
H10A C10 H10C 107(3) . . ?
H10B C10 H10C 112(4) . . ?
O2 C13 O1 129.2(3) . . ?
O2 C13 C12 115.9(3) . . ?
O1 C13 C12 114.9(3) . . ?
N1 C1 C2 107.7(2) . . ?
N1 C1 C8 121.0(2) . . ?
C2 C1 C8 131.3(3) . . ?
N4 C6 C5 107.7(2) . . ?
N4 C6 C11 121.7(3) . . ?
C5 C6 C11 130.5(3) . . ?
C3 C9 H9A 108(2) . . ?
C3 C9 H9B 114(2) . . ?
H9A C9 H9B 105(3) . . ?
C3 C9 H9C 112(2) . . ?
H9A C9 H9C 114(3) . . ?
H9B C9 H9C 104(3) . . ?
O4 C15 O3 129.1(3) . . ?
O4 C15 C14 116.0(2) . . ?
O3 C15 C14 114.9(2) . . ?
C6 C11 H11A 110(3) . . ?
C6 C11 H11B 107(3) . . ?
H11A C11 H11B 111(4) . . ?
C6 C11 H11C 111(3) . . ?
H11A C11 H11C 106(4) . . ?
H11B C11 H11C 111(4) . . ?
F5 C14 F4 109.8(3) . . ?
F5 C14 F6 104.3(3) . . ?
F4 C14 F6 103.4(3) . . ?
F5 C14 C15 114.7(2) . . ?
F4 C14 C15 113.5(2) . . ?
F6 C14 C15 110.0(3) . . ?
C5 C7 C2 114.0(2) . . ?
C5 C7 H7A 108.7(19) . . ?
C2 C7 H7A 111(2) . . ?
C5 C7 H7B 111.4(19) . . ?
C2 C7 H7B 105.3(19) . . ?
H7A C7 H7B 106(3) . . ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
F2 C12 F3 110.7(3) . . ?
F2 C12 F1 105.1(3) . . ?
F3 C12 F1 104.0(3) . . ?
F2 C12 C13 114.4(3) . . ?
F3 C12 C13 111.9(3) . . ?
F1 C12 C13 110.1(3) . . ?

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
N1 H111 O4 0.97(4) 1.70(4) 2.661(3) 173(3) .
N2 H222 O1 0.84(4) 1.84(4) 2.678(3) 171(3) 4_465
N3 H333 O3 0.90(3) 1.77(3) 2.665(3) 173(3) 1_565
N4 H444 O2 0.88(4) 1.80(5) 2.670(3) 173(4) .

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.53
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.755
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.062


