# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry
# This journal is © The Royal Society of Chemistry 2011
data_global
_journal_name_full J.Mater.Chem.
_journal_coden_cambridge 1145
_journal_year ?
_journal_volume ?
_journal_page_first ?
_publ_contact_author_name 'Anna Piecha'
_publ_contact_author_email anna.piecha@chem.uni.wroc.pl
loop_
_publ_author_name
A.Piecha
A.Bialonska
R.Jakubas
data_jak10abs
_database_code_depnum_ccdc_archive 'CCDC 836940'
#TrackingRef 'JAK10ABS.CIF'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety '2(C3 H5 N2), Cl4 Sb, Cl'
_chemical_formula_sum 'C6 H10 Cl5 N4 Sb'
_chemical_formula_weight 437.18
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'
Sb Sb -0.5866 1.5461 '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 'P b c n'
_symmetry_space_group_name_Hall '-P 2n 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
_cell_length_a 10.828(2)
_cell_length_b 20.059(6)
_cell_length_c 14.318(4)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 3109.9(14)
_cell_formula_units_Z 8
_cell_measurement_temperature 193(2)
_cell_measurement_reflns_used 17479
_cell_measurement_theta_min 2.76
_cell_measurement_theta_max 36.53
_exptl_crystal_description plate
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.5012
_exptl_crystal_size_mid 0.4772
_exptl_crystal_size_min 0.1013
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.867
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1680
_exptl_absorpt_coefficient_mu 2.615
_exptl_absorpt_correction_T_min 0.324
_exptl_absorpt_correction_T_max 0.793
_exptl_absorpt_correction_type analytical
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET)
(compiled Jan 12 2007,17:49:11)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 193(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 'Kuma KM4CCD'
_diffrn_measurement_method '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 31019
_diffrn_reflns_av_R_equivalents 0.0343
_diffrn_reflns_av_sigmaI/netI 0.0185
_diffrn_reflns_limit_h_min -15
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -24
_diffrn_reflns_limit_k_max 27
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_theta_min 3.11
_diffrn_reflns_theta_max 30.00
_reflns_number_total 4449
_reflns_number_gt 3647
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_structure_refinement
;
SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0333P)^2^+1.8259P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 4449
_refine_ls_number_parameters 191
_refine_ls_number_restraints 54
_refine_ls_R_factor_all 0.0392
_refine_ls_R_factor_gt 0.0288
_refine_ls_wR_factor_ref 0.0722
_refine_ls_wR_factor_gt 0.0666
_refine_ls_goodness_of_fit_ref 1.114
_refine_ls_restrained_S_all 1.121
_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
Sb Sb 0.320340(14) 0.404782(8) 0.087791(11) 0.03344(6) Uani 1 1 d . . .
Cl1 Cl 0.20498(8) 0.39536(5) -0.05662(6) 0.0586(2) Uani 1 1 d . . .
Cl2 Cl 0.19188(7) 0.32134(4) 0.16532(6) 0.05515(19) Uani 1 1 d . . .
Cl3 Cl 0.46318(6) 0.31262(3) 0.03049(5) 0.04299(15) Uani 1 1 d . . .
Cl4 Cl 0.15555(8) 0.49871(4) 0.14660(7) 0.0632(2) Uani 1 1 d . . .
Cl5 Cl 0.5000 0.5000 0.0000 0.0480(2) Uani 1 2 d S . .
Cl6 Cl 0.5000 0.40042(5) 0.2500 0.04053(19) Uani 1 2 d S . .
N11 N 0.4989(4) 0.60876(18) 0.1775(2) 0.0813(10) Uani 1 1 d . . .
H11 H 0.4842 0.5972 0.1193 0.098 Uiso 1 1 calc R A .
C12 C 0.5000 0.5711(3) 0.2500 0.0724(15) Uani 1 2 d S . .
H12 H 0.5000 0.5237 0.2500 0.087 Uiso 1 2 calc SR . .
C13 C 0.5274(12) 0.6746(7) 0.2129(9) 0.079(3) Uani 0.50 1 d PU A -1
H13A H 0.5423 0.7139 0.1775 0.095 Uiso 0.50 1 calc PR A -1
C14 C 0.5284(11) 0.6688(6) 0.3027(8) 0.070(3) Uani 0.50 1 d PU . -1
H14A H 0.5464 0.7032 0.3462 0.084 Uiso 0.50 1 calc PR . -1
N21 N 0.9152(2) 0.41111(13) 0.09152(19) 0.0516(6) Uani 1 1 d . . .
H21 H 0.9831 0.4344 0.1006 0.062 Uiso 1 1 calc R . .
C22 C 0.8049(3) 0.42822(19) 0.1181(3) 0.0607(9) Uani 1 1 d . . .
H22 H 0.7838 0.4679 0.1507 0.073 Uiso 1 1 calc R . .
N23 N 0.7280(3) 0.38147(17) 0.0925(2) 0.0628(8) Uani 1 1 d . . .
H23 H 0.6479 0.3818 0.1027 0.075 Uiso 1 1 calc R . .
C24 C 0.7903(3) 0.33264(18) 0.0478(3) 0.0567(8) Uani 1 1 d . . .
H24 H 0.7565 0.2930 0.0221 0.068 Uiso 1 1 calc R . .
C25 C 0.9081(3) 0.35108(18) 0.0471(3) 0.0605(9) Uani 1 1 d . . .
H25 H 0.9750 0.3270 0.0206 0.073 Uiso 1 1 calc R . .
N1 N 0.5000 0.2366(4) 0.2500 0.068(3) Uani 0.64 2 d SPU . 1
H1 H 0.5000 0.2851 0.2500 0.082 Uiso 0.64 2 d SP B 1
C2 C 0.4133(9) 0.2020(5) 0.2133(5) 0.068(2) Uani 0.64 1 d PU . 1
H2 H 0.3487 0.2167 0.1880 0.082 Uiso 0.64 1 d P C 1
N3 N 0.4624(18) 0.1334(12) 0.2312(16) 0.045(5) Uani 0.32 1 d PU D -1
H3 H 0.4138 0.0970 0.1993 0.054 Uiso 0.32 1 d P E -1
C4 C 0.566(3) 0.1393(17) 0.285(2) 0.051(6) Uani 0.32 1 d PU D -1
H4 H 0.5862 0.0970 0.3007 0.061 Uiso 0.32 1 d P F -1
N1A N 0.4095(16) 0.1583(8) 0.2297(13) 0.074(5) Uani 0.36 1 d PU G 2
H1A H 0.3362 0.1438 0.2126 0.088 Uiso 0.36 1 calc PR G 2
C2A C 0.5000 0.1226(15) 0.2500 0.048(6) Uani 0.36 2 d SPU . 2
H2A H 0.5000 0.0752 0.2500 0.057 Uiso 0.36 2 calc SPR . 2
C3A C 0.4425(11) 0.2234(7) 0.2383(12) 0.058(4) Uani 0.36 1 d PU . 2
H3A H 0.3913 0.2612 0.2291 0.070 Uiso 0.36 1 calc PR . 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Sb 0.03058(9) 0.03161(10) 0.03814(10) 0.00459(6) -0.00489(6) -0.00425(6)
Cl1 0.0514(4) 0.0750(6) 0.0495(4) 0.0041(4) -0.0201(3) -0.0072(4)
Cl2 0.0440(4) 0.0497(4) 0.0718(5) 0.0154(4) 0.0050(3) -0.0118(3)
Cl3 0.0478(3) 0.0371(3) 0.0441(3) -0.0060(3) -0.0010(3) -0.0022(3)
Cl4 0.0540(4) 0.0438(4) 0.0917(6) -0.0120(4) -0.0019(4) 0.0042(3)
Cl5 0.0626(6) 0.0368(5) 0.0446(5) 0.0019(4) 0.0063(4) -0.0011(4)
Cl6 0.0465(5) 0.0406(5) 0.0346(4) 0.000 0.0004(3) 0.000
N11 0.108(3) 0.094(3) 0.0428(16) -0.0173(17) 0.0091(16) 0.017(2)
C12 0.090(4) 0.033(2) 0.094(4) 0.000 0.018(3) 0.000
C13 0.103(7) 0.064(5) 0.069(6) 0.026(4) 0.011(5) -0.010(6)
C14 0.104(7) 0.052(5) 0.054(5) -0.014(3) 0.006(5) -0.027(5)
N21 0.0399(13) 0.0468(15) 0.0682(18) -0.0055(12) -0.0028(11) -0.0017(10)
C22 0.059(2) 0.0501(19) 0.073(2) -0.0123(17) 0.0102(16) 0.0104(15)
N23 0.0354(13) 0.0686(19) 0.084(2) -0.0073(16) 0.0125(13) 0.0063(13)
C24 0.0398(14) 0.056(2) 0.074(2) -0.0155(16) -0.0001(15) 0.0009(13)
C25 0.0383(14) 0.056(2) 0.087(2) -0.0223(18) 0.0040(16) 0.0062(14)
N1 0.109(7) 0.033(4) 0.063(4) 0.000 -0.020(6) 0.000
C2 0.082(5) 0.068(5) 0.054(4) 0.006(3) -0.024(3) 0.017(4)
N3 0.051(9) 0.037(8) 0.047(7) -0.002(6) -0.011(7) -0.012(7)
C4 0.054(10) 0.037(8) 0.061(9) 0.001(7) -0.007(7) 0.008(7)
N1A 0.068(7) 0.083(9) 0.070(7) -0.013(7) 0.006(6) -0.010(7)
C2A 0.049(10) 0.044(9) 0.050(10) 0.000 -0.004(8) 0.000
C3A 0.047(6) 0.055(7) 0.074(8) 0.017(6) -0.028(6) 0.000(5)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb Cl1 2.4231(9) . ?
Sb Cl2 2.4430(8) . ?
Sb Cl3 2.5462(8) . ?
Sb Cl4 2.7281(9) . ?
Cl6 Cl6 0.0000(19) 3_655 ?
N11 C14 1.273(12) 3_655 ?
N11 C12 1.284(5) . ?
N11 C13 1.449(14) . ?
N11 H11 0.8800 . ?
C12 N11 1.284(5) 3_655 ?
C12 H12 0.9500 . ?
C13 C14 1.291(11) . ?
C13 H13A 0.9500 . ?
C14 N11 1.273(12) 3_655 ?
C14 H14A 0.9500 . ?
N21 C22 1.300(4) . ?
N21 C25 1.364(4) . ?
N21 H21 0.8800 . ?
C22 N23 1.307(5) . ?
C22 H22 0.9500 . ?
N23 C24 1.350(4) . ?
N23 H23 0.8800 . ?
C24 C25 1.329(4) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
N1 N1 0.000(17) 3_655 ?
N1 C2 1.280(10) . ?
N1 C2 1.280(10) 3_655 ?
N1 H1 0.9737 . ?
C2 N1 1.280(10) 3_655 ?
C2 N3 1.50(2) . ?
C2 H2 0.8409 . ?
N3 C4 1.36(3) . ?
N3 H3 1.0090 . ?
C4 H4 0.9063 . ?
N1A C2A 1.25(2) . ?
N1A C3A 1.36(2) . ?
N1A H2 1.4695 . ?
N1A H3 1.3053 . ?
N1A H1A 0.8800 . ?
C2A N1A 1.25(2) 3_655 ?
C2A H3 1.2891 . ?
C2A H4 1.2891 . ?
C2A H2A 0.9500 . ?
C3A C3A 1.29(2) 3_655 ?
C3A H1 1.3964 . ?
C3A H2 1.2529 . ?
C3A H3A 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
Cl1 Sb Cl2 92.34(3) . . ?
Cl1 Sb Cl3 88.94(3) . . ?
Cl2 Sb Cl3 89.70(3) . . ?
Cl1 Sb Cl4 88.86(3) . . ?
Cl2 Sb Cl4 87.74(3) . . ?
Cl3 Sb Cl4 176.55(2) . . ?
C14 N11 C12 112.3(6) 3_655 . ?
C14 N11 C13 26.9(6) 3_655 . ?
C12 N11 C13 104.6(6) . . ?
C14 N11 H11 114.8 3_655 . ?
C12 N11 H11 127.7 . . ?
C13 N11 H11 127.7 . . ?
N11 C12 N11 107.8(5) 3_655 . ?
N11 C12 H12 126.1 3_655 . ?
N11 C12 H12 126.1 . . ?
C14 C13 N11 105.5(12) . . ?
C14 C13 H13A 127.2 . . ?
N11 C13 H13A 127.2 . . ?
N11 C14 C13 107.8(12) 3_655 . ?
N11 C14 H14A 126.1 3_655 . ?
C13 C14 H14A 126.1 . . ?
C22 N21 C25 108.6(3) . . ?
C22 N21 H21 125.7 . . ?
C25 N21 H21 125.7 . . ?
N21 C22 N23 108.3(3) . . ?
N21 C22 H22 125.9 . . ?
N23 C22 H22 125.9 . . ?
C22 N23 C24 109.6(3) . . ?
C22 N23 H23 125.2 . . ?
C24 N23 H23 125.2 . . ?
C25 C24 N23 106.4(3) . . ?
C25 C24 H24 126.8 . . ?
N23 C24 H24 126.8 . . ?
C24 C25 N21 107.2(3) . . ?
C24 C25 H25 126.4 . . ?
N21 C25 H25 126.4 . . ?
N1 N1 C2 0(10) 3_655 . ?
N1 N1 C2 0(10) 3_655 3_655 ?
C2 N1 C2 114.4(11) . 3_655 ?
N1 N1 H1 0.0 3_655 . ?
C2 N1 H1 122.8 . . ?
C2 N1 H1 122.8 3_655 . ?
N1 C2 N1 0.0(6) 3_655 . ?
N1 C2 N3 99.6(11) 3_655 . ?
N1 C2 N3 99.6(11) . . ?
N1 C2 H2 126.6 3_655 . ?
N1 C2 H2 126.6 . . ?
N3 C2 H2 133.7 . . ?
C4 N3 C2 108(3) . . ?
C4 N3 H3 138.3 . . ?
C2 N3 H3 113.7 . . ?
N3 C4 H4 105.0 . . ?
C2A N1A C3A 108.8(19) . . ?
C2A N1A H2 154.6 . . ?
C3A N1A H2 52.4 . . ?
C2A N1A H3 60.6 . . ?
C3A N1A H3 157.8 . . ?
H2 N1A H3 129.1 . . ?
C2A N1A H1A 125.6 . . ?
C3A N1A H1A 125.6 . . ?
H2 N1A H1A 75.4 . . ?
H3 N1A H1A 68.1 . . ?
N1A C2A N1A 110(3) 3_655 . ?
N1A C2A H3 158.2 3_655 . ?
N1A C2A H3 61.9 . . ?
N1A C2A H4 61.9 3_655 . ?
N1A C2A H4 158.2 . . ?
H3 C2A H4 133.1 . . ?
N1A C2A H2A 125.0 3_655 . ?
N1A C2A H2A 125.0 . . ?
H3 C2A H2A 66.5 . . ?
H4 C2A H2A 66.5 . . ?
C3A C3A N1A 106.2(9) 3_655 . ?
C3A C3A H1 62.5 3_655 . ?
N1A C3A H1 168.6 . . ?
C3A C3A H2 158.8 3_655 . ?
N1A C3A H2 68.4 . . ?
H1 C3A H2 121.7 . . ?
C3A C3A H3A 126.9 3_655 . ?
N1A C3A H3A 126.9 . . ?
H1 C3A H3A 64.4 . . ?
H2 C3A H3A 62.0 . . ?
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
C14 N11 C12 N11 -14.7(6) 3_655 . . 3_655 ?
C13 N11 C12 N11 12.5(5) . . . 3_655 ?
C14 N11 C13 C14 104(2) 3_655 . . . ?
C12 N11 C13 C14 -6.8(12) . . . . ?
N11 C13 C14 N11 -1.7(15) . . . 3_655 ?
C25 N21 C22 N23 0.0(5) . . . . ?
N21 C22 N23 C24 0.0(5) . . . . ?
C22 N23 C24 C25 0.0(5) . . . . ?
N23 C24 C25 N21 0.0(4) . . . . ?
C22 N21 C25 C24 0.0(4) . . . . ?
C2 N1 C2 N1 0(100) 3_655 . . 3_655 ?
N1 N1 C2 N3 0.00(8) 3_655 . . . ?
C2 N1 C2 N3 -1.4(9) 3_655 . . . ?
N1 C2 N3 C4 6.0(13) 3_655 . . . ?
N1 C2 N3 C4 6.0(13) . . . . ?
C3A N1A C2A N1A -0.8(10) . . . 3_655 ?
C2A N1A C3A C3A 2(3) . . . 3_655 ?
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 H1 Cl6 0.97 2.31 3.286(8) 180.0 3_655
C2 H2 Cl2 0.84 2.72 3.457(9) 147.2 .
N3 H3 Cl4 1.01 2.24 3.22(2) 164.5 8_655
C4 H4 Cl4 0.91 2.24 3.14(3) 172.1 6_656
N1A H1A Cl4 0.88 3.06 3.488(16) 112.1 8_655
C2A H2A Cl4 0.95 2.72 3.35(2) 124.4 6_656
C2A H2A Cl4 0.95 2.72 3.35(2) 124.4 8_655
C3A H3A Cl2 0.95 2.64 3.510(13) 153.2 .
N11 H11 Cl5 0.88 2.60 3.350(3) 144.1 .
C12 H12 Cl6 0.95 2.47 3.423(5) 180.0 .
C13 H13A Cl3 0.95 3.03 3.496(12) 112.1 5_665
C14 H14A Cl2 0.95 2.85 3.564(11) 132.8 6_666
C14 H14A Cl3 0.95 2.81 3.358(11) 118.0 7_566
N21 H21 Cl4 0.88 2.36 3.237(3) 172.0 1_655
C22 H22 Cl1 0.95 3.06 3.648(4) 121.7 5_665
C22 H22 Cl4 0.95 3.04 3.678(4) 125.9 3_655
N23 H23 Cl3 0.88 2.64 3.304(3) 132.6 .
N23 H23 Cl6 0.88 2.67 3.365(3) 136.3 .
C24 H24 Cl3 0.95 3.20 3.573(3) 105.3 .
C25 H25 Cl2 0.95 3.13 3.558(3) 109.0 1_655
C25 H25 Cl3 0.95 2.90 3.517(3) 124.0 4
_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full 30.00
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max 0.388
_refine_diff_density_min -1.126
_refine_diff_density_rms 0.109
# Attachment 'JAK11ABS.CIF'
data_jak11abs
_database_code_depnum_ccdc_archive 'CCDC 836941'
#TrackingRef 'JAK11ABS.CIF'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety '2(C3 H5 N2), Cl4 Sb, Cl'
_chemical_formula_sum 'C6 H10 Cl5 N4 Sb'
_chemical_formula_weight 437.18
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.5866 1.5461 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting ORTHORHOMBIC
_symmetry_space_group_name_H-M 'P n a 21'
_symmetry_space_group_name_Hall 'P 2c -2n'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
_cell_length_a 14.211(2)
_cell_length_b 19.930(3)
_cell_length_c 10.786(2)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 3054.9(8)
_cell_formula_units_Z 8
_cell_measurement_temperature 100(2)
_cell_measurement_reflns_used 21126
_cell_measurement_theta_min 2.7778
_cell_measurement_theta_max 36.4857
_exptl_crystal_description plate
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.5012
_exptl_crystal_size_mid 0.4772
_exptl_crystal_size_min 0.1013
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.901
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1680
_exptl_absorpt_coefficient_mu 2.662
_exptl_absorpt_correction_T_min 0.371
_exptl_absorpt_correction_T_max 0.799
_exptl_absorpt_correction_type analytical
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET)
(compiled Jan 12 2007,17:49:11)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_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 'Kuma KM4CCD'
_diffrn_measurement_method '\w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number 0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 25092
_diffrn_reflns_av_R_equivalents 0.0241
_diffrn_reflns_av_sigmaI/netI 0.0204
_diffrn_reflns_limit_h_min -18
_diffrn_reflns_limit_h_max 18
_diffrn_reflns_limit_k_min -23
_diffrn_reflns_limit_k_max 26
_diffrn_reflns_limit_l_min -10
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_theta_min 3.04
_diffrn_reflns_theta_max 28.00
_reflns_number_total 5701
_reflns_number_gt 5227
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_structure_refinement
;
SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.)
;
_computing_molecular_graphics ?
_computing_publication_material ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0299P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 5701
_refine_ls_number_parameters 289
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.0226
_refine_ls_R_factor_gt 0.0194
_refine_ls_wR_factor_ref 0.0469
_refine_ls_wR_factor_gt 0.0455
_refine_ls_goodness_of_fit_ref 1.065
_refine_ls_restrained_S_all 1.065
_refine_ls_shift/su_max 0.005
_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
Sb1 Sb 0.603202(9) 0.654452(6) 0.741735(11) 0.01975(3) Uani 1 1 d . . .
Cl1 Cl 0.45804(4) 0.64251(3) 0.85837(5) 0.03215(13) Uani 1 1 d . . .
Cl2 Cl 0.68485(4) 0.57056(2) 0.86639(5) 0.02960(12) Uani 1 1 d . . .
Cl3 Cl 0.54362(4) 0.55929(2) 0.59675(5) 0.02473(11) Uani 1 1 d . . .
Cl4 Cl 0.65979(4) 0.74567(3) 0.90346(5) 0.03387(14) Uani 1 1 d . . .
Cl6 Cl 0.76504(4) 0.64910(2) 0.56060(5) 0.02111(10) Uani 1 1 d . . .
Cl5 Cl 0.51313(4) 0.75090(3) 0.55868(5) 0.02454(10) Uani 1 1 d . . .
Sb1A Sb 0.927918(9) 0.656893(6) 0.376920(10) 0.01608(3) Uani 1 1 d . . .
Cl1A Cl 1.07555(4) 0.65241(3) 0.26550(5) 0.02847(13) Uani 1 1 d . . .
Cl2A Cl 0.85528(4) 0.57397(2) 0.23912(5) 0.02724(11) Uani 1 1 d . . .
Cl3A Cl 0.98298(3) 0.56474(2) 0.51594(4) 0.02129(11) Uani 1 1 d . . .
Cl4A Cl 0.86643(4) 0.75584(2) 0.20933(5) 0.02880(13) Uani 1 1 d . . .
N1 N 0.75686(14) 0.48659(9) 0.5988(2) 0.0394(6) Uani 1 1 d . . .
H1 H 0.7648 0.5277 0.6266 0.047 Uiso 1 1 calc R . .
C2 C 0.72395(18) 0.43759(14) 0.6622(2) 0.0468(7) Uani 1 1 d . . .
H2 H 0.7040 0.4396 0.7462 0.056 Uiso 1 1 calc R . .
N3 N 0.72246(14) 0.38369(10) 0.5909(2) 0.0444(6) Uani 1 1 d . . .
H3 H 0.7022 0.3437 0.6131 0.053 Uiso 1 1 calc R . .
C4 C 0.75716(18) 0.40016(13) 0.4783(3) 0.0417(7) Uani 1 1 d . . .
H4 H 0.7657 0.3713 0.4092 0.050 Uiso 1 1 calc R . .
C5 C 0.77716(16) 0.46598(12) 0.4848(2) 0.0350(6) Uani 1 1 d . . .
H5 H 0.8014 0.4929 0.4195 0.042 Uiso 1 1 calc R . .
N11 N 0.69152(15) 0.85487(10) 0.5677(2) 0.0414(6) Uani 1 1 d . . .
H11 H 0.6344 0.8378 0.5684 0.050 Uiso 1 1 calc R . .
C12 C 0.7692(2) 0.82152(11) 0.5578(3) 0.0387(6) Uani 1 1 d . . .
H12 H 0.7743 0.7742 0.5490 0.046 Uiso 1 1 calc R . .
N13 N 0.84009(15) 0.86377(11) 0.5619(2) 0.0410(6) Uani 1 1 d . . .
H13 H 0.9000 0.8529 0.5578 0.049 Uiso 1 1 calc R . .
C14 C 0.80639(19) 0.92588(13) 0.5734(4) 0.0621(9) Uani 1 1 d . . .
H14 H 0.8426 0.9659 0.5783 0.075 Uiso 1 1 calc R . .
C15 C 0.7140(2) 0.92188(14) 0.5768(4) 0.0833(11) Uani 1 1 d . . .
H15 H 0.6711 0.9582 0.5841 0.100 Uiso 1 1 calc R . .
N21 N 0.60611(14) 0.65783(8) 0.14518(18) 0.0260(5) Uani 1 1 d . . .
H21 H 0.6143 0.6822 0.0780 0.031 Uiso 1 1 calc R . .
C22 C 0.63929(16) 0.67206(11) 0.2556(2) 0.0304(5) Uani 1 1 d . . .
H22 H 0.6769 0.7098 0.2767 0.037 Uiso 1 1 calc R . .
N23 N 0.61096(13) 0.62438(9) 0.33229(18) 0.0292(5) Uani 1 1 d . . .
H23 H 0.6233 0.6231 0.4122 0.035 Uiso 1 1 calc R . .
C24 C 0.55988(16) 0.57749(11) 0.26947(19) 0.0287(5) Uani 1 1 d . . .
H24 H 0.5324 0.5379 0.3027 0.034 Uiso 1 1 calc R . .
C25 C 0.55619(15) 0.59834(11) 0.15145(19) 0.0250(5) Uani 1 1 d . . .
H25 H 0.5252 0.5764 0.0848 0.030 Uiso 1 1 calc R . .
N31 N 0.92671(13) 0.66599(9) 0.97277(19) 0.0271(5) Uani 1 1 d . . .
H31 H 0.9162 0.6891 1.0409 0.032 Uiso 1 1 calc R . .
C32 C 0.89826(16) 0.68261(11) 0.8612(2) 0.0300(6) Uani 1 1 d . . .
H32 H 0.8635 0.7217 0.8402 0.036 Uiso 1 1 calc R . .
N33 N 0.92608(14) 0.63595(10) 0.78342(17) 0.0296(5) Uani 1 1 d . . .
H33 H 0.9154 0.6360 0.7031 0.036 Uiso 1 1 calc R . .
C34 C 0.97395(16) 0.58763(11) 0.84615(19) 0.0298(6) Uani 1 1 d . . .
H34 H 1.0010 0.5481 0.8122 0.036 Uiso 1 1 calc R . .
C35 C 0.97543(18) 0.60678(12) 0.9661(2) 0.0362(6) Uani 1 1 d . . .
H35 H 1.0046 0.5837 1.0329 0.043 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Sb1 0.02135(6) 0.01912(6) 0.01879(6) 0.00417(5) 0.00378(5) 0.00358(5)
Cl1 0.0255(2) 0.0432(3) 0.0278(2) 0.0068(2) 0.0084(2) 0.0050(2)
Cl2 0.0366(3) 0.0260(2) 0.0262(2) 0.0080(2) -0.0013(2) 0.0088(2)
Cl3 0.0232(2) 0.0225(2) 0.0285(2) 0.00356(19) 0.0022(2) -0.00192(19)
Cl4 0.0476(3) 0.0226(3) 0.0314(3) -0.0014(2) 0.0046(2) -0.0035(2)
Cl6 0.0186(2) 0.0209(2) 0.02386(18) 0.0006(2) -0.00092(17) -0.00022(18)
Cl5 0.0236(2) 0.0179(2) 0.0321(2) 0.00242(18) -0.00259(18) 0.00025(17)
Sb1A 0.01935(6) 0.01413(5) 0.01477(5) -0.00142(5) 0.00191(5) -0.00183(4)
Cl1A 0.0258(3) 0.0326(3) 0.0270(2) -0.0017(2) 0.01051(19) 0.0004(2)
Cl2A 0.0380(3) 0.0225(2) 0.0211(2) -0.0038(2) -0.0049(2) -0.00718(19)
Cl3A 0.0258(2) 0.0166(2) 0.0215(2) 0.00038(18) -0.00137(18) 0.00237(18)
Cl4A 0.0424(3) 0.0193(2) 0.0247(2) 0.00273(19) -0.0013(2) 0.0092(2)
N1 0.0401(11) 0.0209(9) 0.0573(12) -0.0083(9) -0.0089(9) 0.0080(8)
C2 0.0343(14) 0.0664(18) 0.0397(13) 0.0096(13) 0.0051(12) -0.0010(13)
N3 0.0321(10) 0.0292(10) 0.0719(15) 0.0266(10) -0.0203(11) -0.0144(8)
C4 0.0388(14) 0.0334(13) 0.0528(14) -0.0154(12) -0.0118(11) 0.0004(10)
C5 0.0290(12) 0.0366(13) 0.0395(12) 0.0121(10) 0.0049(10) -0.0090(10)
N11 0.0256(10) 0.0437(11) 0.0548(12) -0.0150(10) -0.0021(10) -0.0112(9)
C12 0.0520(14) 0.0180(10) 0.0460(11) -0.0035(12) -0.0102(11) 0.0051(11)
N13 0.0233(10) 0.0522(13) 0.0474(12) 0.0064(11) -0.0067(9) 0.0032(9)
C14 0.0365(14) 0.0281(13) 0.122(3) 0.0042(15) -0.0312(16) -0.0099(11)
C15 0.0484(18) 0.0339(14) 0.168(3) -0.0553(18) -0.035(2) 0.0155(12)
N21 0.0332(10) 0.0222(9) 0.0225(9) 0.0012(7) 0.0035(8) 0.0004(7)
C22 0.0311(12) 0.0230(10) 0.0373(12) -0.0066(10) -0.0003(10) -0.0009(9)
N23 0.0378(10) 0.0286(10) 0.0211(8) 0.0004(8) -0.0074(8) -0.0023(8)
C24 0.0391(12) 0.0260(11) 0.0211(10) 0.0001(9) 0.0019(9) -0.0035(9)
C25 0.0259(10) 0.0268(11) 0.0224(9) -0.0030(9) -0.0021(9) -0.0048(8)
N31 0.0318(10) 0.0273(10) 0.0220(9) -0.0032(8) 0.0000(8) 0.0046(7)
C32 0.0372(13) 0.0253(11) 0.0274(11) 0.0037(10) -0.0017(10) 0.0074(9)
N33 0.0393(11) 0.0344(10) 0.0151(8) 0.0048(8) -0.0032(8) 0.0006(8)
C34 0.0397(13) 0.0275(11) 0.0221(10) -0.0007(9) 0.0083(8) 0.0095(9)
C35 0.0568(15) 0.0327(12) 0.0191(10) 0.0021(9) -0.0133(10) 0.0173(11)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb1 Cl1 2.4279(6) . ?
Sb1 Cl2 2.4392(5) . ?
Sb1 Cl3 2.5999(6) . ?
Sb1 Cl4 2.6447(6) . ?
Sb1A Cl1A 2.4195(6) . ?
Sb1A Cl2A 2.4507(5) . ?
Sb1A Cl3A 2.4968(6) . ?
Sb1A Cl4A 2.8142(6) . ?
N1 C2 1.281(3) . ?
N1 C5 1.329(3) . ?
N1 H1 0.8800 . ?
C2 N3 1.322(3) . ?
C2 H2 0.9500 . ?
N3 C4 1.351(3) . ?
N3 H3 0.8800 . ?
C4 C5 1.344(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
N11 C12 1.293(3) . ?
N11 C15 1.377(3) . ?
N11 H11 0.8800 . ?
C12 N13 1.313(3) . ?
C12 H12 0.9500 . ?
N13 C14 1.333(3) . ?
N13 H13 0.8800 . ?
C14 C15 1.316(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N21 C22 1.312(3) . ?
N21 C25 1.383(3) . ?
N21 H21 0.8800 . ?
C22 N23 1.323(3) . ?
C22 H22 0.9500 . ?
N23 C24 1.364(3) . ?
N23 H23 0.8800 . ?
C24 C25 1.340(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
N31 C32 1.313(3) . ?
N31 C35 1.370(3) . ?
N31 H31 0.8800 . ?
C32 N33 1.313(3) . ?
C32 H32 0.9500 . ?
N33 C34 1.359(3) . ?
N33 H33 0.8800 . ?
C34 C35 1.349(3) . ?
C34 H34 0.9500 . ?
C35 H35 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
Cl1 Sb1 Cl2 92.94(2) . . ?
Cl1 Sb1 Cl3 87.90(2) . . ?
Cl2 Sb1 Cl3 89.22(2) . . ?
Cl1 Sb1 Cl4 89.08(2) . . ?
Cl2 Sb1 Cl4 87.88(2) . . ?
Cl3 Sb1 Cl4 175.707(17) . . ?
Cl1A Sb1A Cl2A 92.24(2) . . ?
Cl1A Sb1A Cl3A 89.964(19) . . ?
Cl2A Sb1A Cl3A 90.01(2) . . ?
Cl1A Sb1A Cl4A 88.629(19) . . ?
Cl2A Sb1A Cl4A 87.26(2) . . ?
Cl3A Sb1A Cl4A 176.877(16) . . ?
C2 N1 C5 109.7(2) . . ?
C2 N1 H1 125.1 . . ?
C5 N1 H1 125.1 . . ?
N1 C2 N3 108.4(2) . . ?
N1 C2 H2 125.8 . . ?
N3 C2 H2 125.8 . . ?
C2 N3 C4 108.7(2) . . ?
C2 N3 H3 125.7 . . ?
C4 N3 H3 125.7 . . ?
C5 C4 N3 105.5(2) . . ?
C5 C4 H4 127.2 . . ?
N3 C4 H4 127.2 . . ?
N1 C5 C4 107.7(2) . . ?
N1 C5 H5 126.2 . . ?
C4 C5 H5 126.2 . . ?
C12 N11 C15 107.9(2) . . ?
C12 N11 H11 126.1 . . ?
C15 N11 H11 126.1 . . ?
N11 C12 N13 108.8(2) . . ?
N11 C12 H12 125.6 . . ?
N13 C12 H12 125.6 . . ?
C12 N13 C14 108.9(2) . . ?
C12 N13 H13 125.6 . . ?
C14 N13 H13 125.6 . . ?
C15 C14 N13 107.7(2) . . ?
C15 C14 H14 126.1 . . ?
N13 C14 H14 126.1 . . ?
C14 C15 N11 106.7(3) . . ?
C14 C15 H15 126.6 . . ?
N11 C15 H15 126.6 . . ?
C22 N21 C25 108.98(18) . . ?
C22 N21 H21 125.5 . . ?
C25 N21 H21 125.5 . . ?
N21 C22 N23 107.64(19) . . ?
N21 C22 H22 126.2 . . ?
N23 C22 H22 126.2 . . ?
C22 N23 C24 110.10(19) . . ?
C22 N23 H23 124.9 . . ?
C24 N23 H23 125.0 . . ?
C25 C24 N23 106.3(2) . . ?
C25 C24 H24 126.9 . . ?
N23 C24 H24 126.9 . . ?
C24 C25 N21 106.99(19) . . ?
C24 C25 H25 126.5 . . ?
N21 C25 H25 126.5 . . ?
C32 N31 C35 108.94(19) . . ?
C32 N31 H31 125.5 . . ?
C35 N31 H31 125.5 . . ?
N31 C32 N33 108.3(2) . . ?
N31 C32 H32 125.8 . . ?
N33 C32 H32 125.8 . . ?
C32 N33 C34 109.55(19) . . ?
C32 N33 H33 125.2 . . ?
C34 N33 H33 125.2 . . ?
C35 C34 N33 106.5(2) . . ?
C35 C34 H34 126.7 . . ?
N33 C34 H34 126.7 . . ?
C34 C35 N31 106.6(2) . . ?
C34 C35 H35 126.7 . . ?
N31 C35 H35 126.7 . . ?
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
C5 N1 C2 N3 0.3(3) . . . . ?
N1 C2 N3 C4 0.7(3) . . . . ?
C2 N3 C4 C5 -1.4(3) . . . . ?
C2 N1 C5 C4 -1.2(3) . . . . ?
N3 C4 C5 N1 1.5(3) . . . . ?
C15 N11 C12 N13 0.9(4) . . . . ?
N11 C12 N13 C14 -0.7(4) . . . . ?
C12 N13 C14 C15 0.2(4) . . . . ?
N13 C14 C15 N11 0.3(5) . . . . ?
C12 N11 C15 C14 -0.8(4) . . . . ?
C25 N21 C22 N23 -1.0(3) . . . . ?
N21 C22 N23 C24 1.3(3) . . . . ?
C22 N23 C24 C25 -1.0(3) . . . . ?
N23 C24 C25 N21 0.3(2) . . . . ?
C22 N21 C25 C24 0.4(3) . . . . ?
C35 N31 C32 N33 0.6(3) . . . . ?
N31 C32 N33 C34 0.0(3) . . . . ?
C32 N33 C34 C35 -0.6(3) . . . . ?
N33 C34 C35 N31 1.0(3) . . . . ?
C32 N31 C35 C34 -1.0(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 H1 Cl6 0.88 2.52 3.267(2) 142.9 .
N1 H1 Cl2 0.88 2.95 3.489(2) 121.2 .
N3 H3 Cl4A 0.88 2.26 3.118(2) 165.5 4_645
N11 H11 Cl5 0.88 2.45 3.276(2) 157.5 .
N11 H11 Cl3A 0.88 2.95 3.415(2) 114.5 3_465
N13 H13 Cl5 0.88 2.62 3.357(2) 142.1 3_565
N13 H13 Cl3 0.88 2.72 3.295(2) 124.0 3_565
N21 H21 Cl4 0.88 2.36 3.232(2) 171.7 1_554
N23 H23 Cl6 0.88 2.62 3.332(2) 138.1 .
N23 H23 Cl3 0.88 2.62 3.276(2) 132.3 .
N31 H31 Cl4A 0.88 2.36 3.233(2) 171.4 1_556
N33 H33 Cl6 0.88 2.64 3.329(2) 135.4 .
N33 H33 Cl3A 0.88 2.65 3.315(2) 133.5 .
_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full 28.00
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max 0.367
_refine_diff_density_min -0.576
_refine_diff_density_rms 0.107