# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013
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# Cambridge Crystallographic Data Centre
# CCDC
#
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#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
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# fide research purposes only. It may contain copyright material
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data_mo_scan_0m
_database_code_depnum_ccdc_archive 'CCDC 932700'
#TrackingRef '19245_web_deposit_cif_file_0_ChristianGanter_1365162269.Compound 4.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C16 H26 N3, F6 P'
_chemical_formula_sum 'C16 H26 F6 N3 P'
_chemical_formula_weight 405.37
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_space_group_name_Hall '-P 2ybc'
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 10.098(2)
_cell_length_b 19.944(5)
_cell_length_c 10.579(2)
_cell_angle_alpha 90.00
_cell_angle_beta 103.041(5)
_cell_angle_gamma 90.00
_cell_volume 2075.7(8)
_cell_formula_units_Z 4
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 5969
_cell_measurement_theta_min 2.225
_cell_measurement_theta_max 23.702
_exptl_crystal_description needle
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.5
_exptl_crystal_size_mid 0.1
_exptl_crystal_size_min 0.1
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.297
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 848
_exptl_absorpt_coefficient_mu 0.188
_exptl_absorpt_correction_type Multi-scan
_exptl_absorpt_correction_T_min 0.6219
_exptl_absorpt_correction_T_max 0.7460
_exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'microfocus sealed tube'
_diffrn_radiation_monochromator 'multilayer mirror'
_diffrn_measurement_device_type 'Bruker Kappa APEX II CCD area detector'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 18698
_diffrn_reflns_av_R_equivalents 0.0397
_diffrn_reflns_av_sigmaI/netI 0.0258
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -23
_diffrn_reflns_limit_k_max 23
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 2.04
_diffrn_reflns_theta_max 25.25
_reflns_number_total 3758
_reflns_number_gt 2979
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'APEX2 (Bruker, 2006)'
_computing_cell_refinement 'SAINT (Bruker, 2006)'
_computing_data_reduction SAINT
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-3 (University of Glasgow, 2008)'
_computing_publication_material 'Bruker SHELXTL'
_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^)+(0.0200P)^2^+2.0000P] 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 mixed
_refine_ls_extinction_method SHELXL
_refine_ls_extinction_coef 0.0097(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 3758
_refine_ls_number_parameters 242
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0825
_refine_ls_R_factor_gt 0.0691
_refine_ls_wR_factor_ref 0.1450
_refine_ls_wR_factor_gt 0.1403
_refine_ls_goodness_of_fit_ref 1.183
_refine_ls_restrained_S_all 1.183
_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
P1 P 0.28201(10) 0.15176(5) 0.64557(8) 0.0686(3) Uani 1 1 d . . .
F1 F 0.1367(3) 0.11668(17) 0.5970(3) 0.1463(12) Uani 1 1 d . . .
F2 F 0.2166(3) 0.20293(16) 0.7257(3) 0.1572(14) Uani 1 1 d . . .
F3 F 0.4185(3) 0.18796(16) 0.6913(3) 0.1365(11) Uani 1 1 d . . .
F4 F 0.2456(3) 0.19899(15) 0.5263(3) 0.1395(11) Uani 1 1 d . . .
F5 F 0.3070(5) 0.10404(17) 0.7629(3) 0.208(2) Uani 1 1 d . . .
F6 F 0.3396(3) 0.10037(15) 0.5607(3) 0.1381(11) Uani 1 1 d . . .
C6 C 0.0884(3) 0.09226(13) 0.1753(3) 0.0492(7) Uani 1 1 d . . .
C3 C -0.1427(3) 0.02540(17) 0.1725(4) 0.0701(9) Uani 1 1 d . . .
H88 H -0.2207 0.0010 0.1747 0.084 Uiso 1 1 calc R . .
N3 N -0.1323(2) 0.05097(12) 0.0588(3) 0.0600(7) Uani 1 1 d . . .
C14 C -0.2574(4) 0.1841(2) -0.1067(4) 0.0837(11) Uani 1 1 d . . .
H7 H -0.3201 0.2207 -0.1293 0.126 Uiso 1 1 calc R . .
H8 H -0.2086 0.1888 -0.0181 0.126 Uiso 1 1 calc R . .
H1 H -0.3066 0.1425 -0.1169 0.126 Uiso 1 1 calc R . .
C13 C -0.1570(3) 0.18456(17) -0.1955(3) 0.0649(8) Uani 1 1 d . . .
C12 C -0.0614(3) 0.12375(16) -0.1696(3) 0.0590(8) Uani 1 1 d . . .
H13 H -0.1153 0.0833 -0.1900 0.071 Uiso 1 1 calc R . .
H12 H -0.0002 0.1259 -0.2282 0.071 Uiso 1 1 calc R . .
N2 N 0.0208(2) 0.11826(12) -0.0354(2) 0.0508(6) Uani 1 1 d . . .
C1 C 0.1453(3) 0.14329(14) 0.0112(3) 0.0545(7) Uani 1 1 d . . .
H14 H 0.1943 0.1678 -0.0376 0.065 Uiso 1 1 calc R . .
N1 N 0.1898(2) 0.12855(11) 0.1363(2) 0.0518(6) Uani 1 1 d . . .
C7 C 0.3246(3) 0.14600(15) 0.2189(3) 0.0616(8) Uani 1 1 d . . .
H17 H 0.3157 0.1502 0.3079 0.074 Uiso 1 1 calc R . .
H18 H 0.3516 0.1894 0.1920 0.074 Uiso 1 1 calc R . .
C8 C 0.4375(3) 0.09558(18) 0.2147(3) 0.0662(9) Uani 1 1 d . . .
C9 C 0.4662(4) 0.0934(3) 0.0791(4) 0.125(2) Uani 1 1 d . . .
H22 H 0.5419 0.0642 0.0795 0.188 Uiso 1 1 calc R . .
H23 H 0.4873 0.1377 0.0541 0.188 Uiso 1 1 calc R . .
H2 H 0.3875 0.0769 0.0185 0.188 Uiso 1 1 calc R . .
C10 C 0.5633(4) 0.1209(2) 0.3130(4) 0.1083(16) Uani 1 1 d . . .
H3 H 0.5420 0.1257 0.3965 0.162 Uiso 1 1 calc R . .
H25 H 0.5904 0.1635 0.2852 0.162 Uiso 1 1 calc R . .
H24 H 0.6362 0.0893 0.3188 0.162 Uiso 1 1 calc R . .
C5 C 0.0743(3) 0.06593(16) 0.2927(3) 0.0642(8) Uani 1 1 d . . .
H16 H 0.1411 0.0706 0.3687 0.077 Uiso 1 1 calc R . .
C4 C -0.0452(4) 0.03252(18) 0.2886(4) 0.0753(10) Uani 1 1 d . . .
H15 H -0.0617 0.0143 0.3645 0.090 Uiso 1 1 calc R . .
C2 C -0.0168(3) 0.08459(13) 0.0662(3) 0.0485(6) Uani 1 1 d . . .
C16 C -0.2372(4) 0.1766(2) -0.3370(4) 0.1007(14) Uani 1 1 d . . .
H6 H -0.2972 0.2142 -0.3604 0.151 Uiso 1 1 calc R . .
H4 H -0.2894 0.1360 -0.3454 0.151 Uiso 1 1 calc R . .
H5 H -0.1749 0.1748 -0.3933 0.151 Uiso 1 1 calc R . .
C15 C -0.0763(4) 0.2495(2) -0.1794(5) 0.1040(15) Uani 1 1 d . . .
H11 H -0.0135 0.2490 -0.2354 0.156 Uiso 1 1 calc R . .
H9 H -0.0270 0.2539 -0.0909 0.156 Uiso 1 1 calc R . .
H10 H -0.1373 0.2867 -0.2018 0.156 Uiso 1 1 calc R . .
C11 C 0.4011(4) 0.0265(2) 0.2540(5) 0.1114(16) Uani 1 1 d . . .
H19 H 0.3816 0.0285 0.3387 0.167 Uiso 1 1 calc R . .
H21 H 0.4760 -0.0035 0.2559 0.167 Uiso 1 1 calc R . .
H20 H 0.3225 0.0104 0.1926 0.167 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
P1 0.0883(7) 0.0641(6) 0.0567(5) 0.0021(4) 0.0233(5) -0.0083(5)
F1 0.143(3) 0.167(3) 0.140(2) -0.051(2) 0.055(2) -0.076(2)
F2 0.167(3) 0.139(2) 0.206(3) -0.086(2) 0.128(3) -0.053(2)
F3 0.0754(16) 0.154(3) 0.171(3) -0.032(2) 0.0091(17) -0.0193(16)
F4 0.158(3) 0.137(2) 0.121(2) 0.0625(19) 0.0244(19) 0.026(2)
F5 0.384(6) 0.131(3) 0.0855(19) 0.0434(18) 0.005(3) -0.055(3)
F6 0.161(3) 0.122(2) 0.132(2) -0.0342(18) 0.034(2) 0.0403(19)
C6 0.0501(16) 0.0423(15) 0.0542(16) -0.0018(12) 0.0096(13) 0.0026(12)
C3 0.0585(19) 0.064(2) 0.091(3) 0.0121(19) 0.0237(18) -0.0049(16)
N3 0.0491(14) 0.0558(15) 0.0733(17) 0.0016(13) 0.0103(12) -0.0027(12)
C14 0.069(2) 0.095(3) 0.085(3) 0.011(2) 0.0156(19) 0.026(2)
C13 0.0554(18) 0.072(2) 0.0618(19) 0.0103(16) 0.0017(15) 0.0043(16)
C12 0.0551(17) 0.071(2) 0.0487(16) -0.0031(14) 0.0065(13) 0.0006(15)
N2 0.0444(13) 0.0524(14) 0.0533(14) 0.0013(11) 0.0063(10) 0.0030(10)
C1 0.0471(16) 0.0525(17) 0.0633(18) 0.0044(14) 0.0114(14) 0.0005(13)
N1 0.0467(13) 0.0485(13) 0.0568(14) -0.0012(11) 0.0047(11) -0.0016(11)
C7 0.0552(17) 0.0545(18) 0.0684(19) -0.0099(15) 0.0000(15) -0.0090(14)
C8 0.0467(17) 0.077(2) 0.068(2) -0.0159(17) -0.0023(14) 0.0009(15)
C9 0.077(3) 0.212(6) 0.085(3) -0.021(3) 0.014(2) 0.034(3)
C10 0.056(2) 0.135(4) 0.116(3) -0.034(3) -0.018(2) -0.003(2)
C5 0.067(2) 0.067(2) 0.0562(18) 0.0028(15) 0.0088(15) 0.0017(16)
C4 0.079(2) 0.079(2) 0.071(2) 0.0168(18) 0.0248(19) 0.0002(19)
C2 0.0458(15) 0.0432(15) 0.0560(16) -0.0002(12) 0.0100(12) 0.0043(12)
C16 0.089(3) 0.134(4) 0.068(2) 0.025(2) -0.007(2) 0.003(3)
C15 0.079(3) 0.072(3) 0.151(4) 0.021(3) 0.004(3) 0.002(2)
C11 0.079(3) 0.074(3) 0.168(5) 0.001(3) -0.001(3) 0.021(2)
_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
P1 F3 1.535(3) . ?
P1 F5 1.539(3) . ?
P1 F4 1.551(3) . ?
P1 F6 1.559(3) . ?
P1 F2 1.565(3) . ?
P1 F1 1.602(3) . ?
C6 C5 1.384(4) . ?
C6 C2 1.390(4) . ?
C6 N1 1.390(4) . ?
C3 N3 1.333(4) . ?
C3 C4 1.398(5) . ?
C3 H88 0.9300 . ?
N3 C2 1.332(3) . ?
C14 C13 1.530(5) . ?
C14 H7 0.9600 . ?
C14 H8 0.9600 . ?
C14 H1 0.9600 . ?
C13 C15 1.520(5) . ?
C13 C12 1.536(4) . ?
C13 C16 1.541(5) . ?
C12 N2 1.478(3) . ?
C12 H13 0.9700 . ?
C12 H12 0.9700 . ?
N2 C1 1.339(3) . ?
N2 C2 1.390(3) . ?
C1 N1 1.331(4) . ?
C1 H14 0.9300 . ?
N1 C7 1.484(3) . ?
C7 C8 1.528(4) . ?
C7 H17 0.9700 . ?
C7 H18 0.9700 . ?
C8 C11 1.509(5) . ?
C8 C9 1.526(5) . ?
C8 C10 1.535(4) . ?
C9 H22 0.9600 . ?
C9 H23 0.9600 . ?
C9 H2 0.9600 . ?
C10 H3 0.9600 . ?
C10 H25 0.9600 . ?
C10 H24 0.9600 . ?
C5 C4 1.371(5) . ?
C5 H16 0.9300 . ?
C4 H15 0.9300 . ?
C16 H6 0.9600 . ?
C16 H4 0.9600 . ?
C16 H5 0.9600 . ?
C15 H11 0.9600 . ?
C15 H9 0.9600 . ?
C15 H10 0.9600 . ?
C11 H19 0.9600 . ?
C11 H21 0.9600 . ?
C11 H20 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
F3 P1 F5 93.7(2) . . ?
F3 P1 F4 90.10(18) . . ?
F5 P1 F4 175.8(2) . . ?
F3 P1 F6 93.76(18) . . ?
F5 P1 F6 92.5(2) . . ?
F4 P1 F6 88.94(17) . . ?
F3 P1 F2 88.95(17) . . ?
F5 P1 F2 88.8(2) . . ?
F4 P1 F2 89.6(2) . . ?
F6 P1 F2 176.93(19) . . ?
F3 P1 F1 177.84(19) . . ?
F5 P1 F1 87.7(2) . . ?
F4 P1 F1 88.44(18) . . ?
F6 P1 F1 87.80(17) . . ?
F2 P1 F1 89.44(17) . . ?
C5 C6 C2 119.3(3) . . ?
C5 C6 N1 134.0(3) . . ?
C2 C6 N1 106.6(2) . . ?
N3 C3 C4 124.8(3) . . ?
N3 C3 H88 117.6 . . ?
C4 C3 H88 117.6 . . ?
C2 N3 C3 112.7(3) . . ?
C13 C14 H7 109.5 . . ?
C13 C14 H8 109.5 . . ?
H7 C14 H8 109.5 . . ?
C13 C14 H1 109.5 . . ?
H7 C14 H1 109.5 . . ?
H8 C14 H1 109.5 . . ?
C15 C13 C14 110.5(3) . . ?
C15 C13 C12 110.7(3) . . ?
C14 C13 C12 111.3(3) . . ?
C15 C13 C16 110.3(3) . . ?
C14 C13 C16 108.7(3) . . ?
C12 C13 C16 105.3(3) . . ?
N2 C12 C13 115.1(2) . . ?
N2 C12 H13 108.5 . . ?
C13 C12 H13 108.5 . . ?
N2 C12 H12 108.5 . . ?
C13 C12 H12 108.5 . . ?
H13 C12 H12 107.5 . . ?
C1 N2 C2 107.1(2) . . ?
C1 N2 C12 127.0(3) . . ?
C2 N2 C12 125.9(2) . . ?
N1 C1 N2 111.2(3) . . ?
N1 C1 H14 124.4 . . ?
N2 C1 H14 124.4 . . ?
C1 N1 C6 107.7(2) . . ?
C1 N1 C7 126.3(3) . . ?
C6 N1 C7 125.9(2) . . ?
N1 C7 C8 114.8(2) . . ?
N1 C7 H17 108.6 . . ?
C8 C7 H17 108.6 . . ?
N1 C7 H18 108.6 . . ?
C8 C7 H18 108.6 . . ?
H17 C7 H18 107.5 . . ?
C11 C8 C9 110.1(4) . . ?
C11 C8 C7 111.3(3) . . ?
C9 C8 C7 110.3(3) . . ?
C11 C8 C10 109.2(3) . . ?
C9 C8 C10 110.0(3) . . ?
C7 C8 C10 105.8(3) . . ?
C8 C9 H22 109.5 . . ?
C8 C9 H23 109.5 . . ?
H22 C9 H23 109.5 . . ?
C8 C9 H2 109.5 . . ?
H22 C9 H2 109.5 . . ?
H23 C9 H2 109.5 . . ?
C8 C10 H3 109.5 . . ?
C8 C10 H25 109.5 . . ?
H3 C10 H25 109.5 . . ?
C8 C10 H24 109.5 . . ?
H3 C10 H24 109.5 . . ?
H25 C10 H24 109.5 . . ?
C4 C5 C6 115.1(3) . . ?
C4 C5 H16 122.5 . . ?
C6 C5 H16 122.5 . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 H15 119.4 . . ?
C3 C4 H15 119.4 . . ?
N3 C2 C6 126.8(3) . . ?
N3 C2 N2 125.8(3) . . ?
C6 C2 N2 107.3(2) . . ?
C13 C16 H6 109.5 . . ?
C13 C16 H4 109.5 . . ?
H6 C16 H4 109.5 . . ?
C13 C16 H5 109.5 . . ?
H6 C16 H5 109.5 . . ?
H4 C16 H5 109.5 . . ?
C13 C15 H11 109.5 . . ?
C13 C15 H9 109.5 . . ?
H11 C15 H9 109.5 . . ?
C13 C15 H10 109.5 . . ?
H11 C15 H10 109.5 . . ?
H9 C15 H10 109.5 . . ?
C8 C11 H19 109.5 . . ?
C8 C11 H21 109.5 . . ?
H19 C11 H21 109.5 . . ?
C8 C11 H20 109.5 . . ?
H19 C11 H20 109.5 . . ?
H21 C11 H20 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
C4 C3 N3 C2 0.3(5) . . . . ?
C15 C13 C12 N2 64.5(4) . . . . ?
C14 C13 C12 N2 -58.7(4) . . . . ?
C16 C13 C12 N2 -176.3(3) . . . . ?
C13 C12 N2 C1 -91.3(4) . . . . ?
C13 C12 N2 C2 90.0(3) . . . . ?
C2 N2 C1 N1 -0.6(3) . . . . ?
C12 N2 C1 N1 -179.5(3) . . . . ?
N2 C1 N1 C6 -0.6(3) . . . . ?
N2 C1 N1 C7 177.9(2) . . . . ?
C5 C6 N1 C1 -177.2(3) . . . . ?
C2 C6 N1 C1 1.7(3) . . . . ?
C5 C6 N1 C7 4.2(5) . . . . ?
C2 C6 N1 C7 -176.9(2) . . . . ?
C1 N1 C7 C8 -86.4(4) . . . . ?
C6 N1 C7 C8 91.9(4) . . . . ?
N1 C7 C8 C11 -57.6(4) . . . . ?
N1 C7 C8 C9 64.8(4) . . . . ?
N1 C7 C8 C10 -176.2(3) . . . . ?
C2 C6 C5 C4 1.3(4) . . . . ?
N1 C6 C5 C4 -179.9(3) . . . . ?
C6 C5 C4 C3 1.1(5) . . . . ?
N3 C3 C4 C5 -2.0(6) . . . . ?
C3 N3 C2 C6 2.4(4) . . . . ?
C3 N3 C2 N2 -178.1(3) . . . . ?
C5 C6 C2 N3 -3.4(5) . . . . ?
N1 C6 C2 N3 177.6(3) . . . . ?
C5 C6 C2 N2 177.1(3) . . . . ?
N1 C6 C2 N2 -2.0(3) . . . . ?
C1 N2 C2 N3 -177.9(3) . . . . ?
C12 N2 C2 N3 1.0(4) . . . . ?
C1 N2 C2 C6 1.7(3) . . . . ?
C12 N2 C2 C6 -179.4(2) . . . . ?
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full 25.25
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max 0.499
_refine_diff_density_min -0.368
_refine_diff_density_rms 0.058
data_mo_scan_0m_p-1
_database_code_depnum_ccdc_archive 'CCDC 932701'
#TrackingRef '19246_web_deposit_cif_file_1_ChristianGanter_1365162269.Compound 5a.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C13 H21 N3, 2(C F3 O3 S)'
_chemical_formula_sum 'C15 H21 F6 N3 O6 S2'
_chemical_formula_weight 517.47
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'
S S 0.1246 0.1234 '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'
_symmetry_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 6.6711(11)
_cell_length_b 12.796(2)
_cell_length_c 14.462(2)
_cell_angle_alpha 102.692(11)
_cell_angle_beta 92.911(11)
_cell_angle_gamma 104.750(11)
_cell_volume 1157.2(3)
_cell_formula_units_Z 2
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 2608
_cell_measurement_theta_min 2.485
_cell_measurement_theta_max 24.242
_exptl_crystal_description Needle
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.5
_exptl_crystal_size_mid 0.1
_exptl_crystal_size_min 0.1
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.485
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 532
_exptl_absorpt_coefficient_mu 0.313
_exptl_absorpt_correction_type Multi-scan
_exptl_absorpt_correction_T_min 0.8717
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 293(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'microfocus sealed tube'
_diffrn_radiation_monochromator 'multilayer mirror'
_diffrn_measurement_device_type 'Bruker Kappa APEX II CCD area detector'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 10200
_diffrn_reflns_av_R_equivalents 0.0264
_diffrn_reflns_av_sigmaI/netI 0.0326
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_limit_l_max 17
_diffrn_reflns_theta_min 1.95
_diffrn_reflns_theta_max 25.00
_reflns_number_total 4063
_reflns_number_gt 2641
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'APEX2 (Bruker, 2006)'
_computing_cell_refinement 'SAINT (Bruker, 2006)'
_computing_data_reduction SAINT
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-3 (University of Glasgow, 2008)'
_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^)+(0.0888P)^2^+0.7528P] 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 mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 4063
_refine_ls_number_parameters 294
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0999
_refine_ls_R_factor_gt 0.0679
_refine_ls_wR_factor_ref 0.2067
_refine_ls_wR_factor_gt 0.1939
_refine_ls_goodness_of_fit_ref 1.121
_refine_ls_restrained_S_all 1.121
_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
S1 S 0.25118(18) 0.21483(9) -0.54194(8) 0.0722(4) Uani 1 1 d . . .
S2 S 0.4812(2) 0.18240(9) -0.08231(8) 0.0759(4) Uani 1 1 d . . .
O6 O 0.0664(6) 0.2477(4) -0.5189(3) 0.1346(16) Uani 1 1 d . . .
F6 F 0.6313(6) 0.2849(4) -0.4619(3) 0.1503(16) Uani 1 1 d . . .
F4 F 0.4014(7) 0.2932(3) -0.3652(2) 0.1504(16) Uani 1 1 d . . .
O4 O 0.2478(8) 0.1080(3) -0.5346(3) 0.1287(15) Uani 1 1 d . . .
O5 O 0.3246(6) 0.2397(3) -0.6269(2) 0.0982(11) Uani 1 1 d . . .
F5 F 0.4771(7) 0.4090(3) -0.4479(3) 0.1453(15) Uani 1 1 d . . .
F1 F 0.5271(14) 0.3786(4) 0.0139(5) 0.253(4) Uani 1 1 d . . .
F2 F 0.4609(13) 0.3569(4) -0.1349(4) 0.251(4) Uani 1 1 d . . .
F3 F 0.7550(14) 0.3595(7) -0.0759(8) 0.326(7) Uani 1 1 d . . .
C8 C 0.9848(9) -0.1047(4) 0.2919(4) 0.0911(15) Uani 1 1 d . . .
H99A H 1.0133 -0.0719 0.3592 0.137 Uiso 1 1 calc R . .
H99B H 1.0799 -0.1484 0.2728 0.137 Uiso 1 1 calc R . .
H99C H 0.8442 -0.1516 0.2776 0.137 Uiso 1 1 calc R . .
C7 C 0.6748(9) 0.0199(4) 0.3863(3) 0.0909(15) Uani 1 1 d . . .
H88A H 0.5743 0.0537 0.4165 0.136 Uiso 1 1 calc R . .
H88B H 0.7849 0.0238 0.4334 0.136 Uiso 1 1 calc R . .
H88C H 0.6081 -0.0567 0.3555 0.136 Uiso 1 1 calc R . .
O2 O 0.4944(6) 0.1345(4) -0.1780(2) 0.1194(14) Uani 1 1 d . . .
O1 O 0.2681(7) 0.1650(5) -0.0634(4) 0.1559(19) Uani 1 1 d . . .
O3 O 0.6173(7) 0.1634(3) -0.0137(3) 0.1204(14) Uani 1 1 d . . .
N3 N 1.0108(6) -0.0160(3) 0.2398(3) 0.0708(9) Uani 1 1 d . . .
C3 C 1.1432(8) -0.0137(5) 0.1725(4) 0.0933(15) Uani 1 1 d . . .
H66 H 1.2185 -0.0663 0.1625 0.112 Uiso 1 1 calc R . .
C15 C 0.4460(9) 0.3051(4) -0.4484(4) 0.0878(14) Uani 1 1 d . . .
C13 C 0.8628(11) 0.5063(5) 0.2177(5) 0.121(2) Uani 1 1 d . . .
H1 H 0.7195 0.5024 0.2261 0.182 Uiso 1 1 calc R . .
H4 H 0.8796 0.4940 0.1510 0.182 Uiso 1 1 calc R . .
H3 H 0.9493 0.5786 0.2507 0.182 Uiso 1 1 calc R . .
C10 C 0.9266(8) 0.4171(4) 0.2581(3) 0.0807(13) Uani 1 1 d . . .
C9 C 0.7798(8) 0.3065(4) 0.2017(3) 0.0775(12) Uani 1 1 d . . .
H11 H 0.6371 0.3100 0.2067 0.093 Uiso 1 1 calc R . .
H12 H 0.8021 0.2970 0.1350 0.093 Uiso 1 1 calc R . .
N1 N 0.8058(5) 0.2078(3) 0.2333(2) 0.0620(8) Uani 1 1 d . . .
C6 C 0.9340(6) 0.1412(3) 0.2003(2) 0.0594(10) Uani 1 1 d . . .
C2 C 0.9063(6) 0.0620(3) 0.2525(3) 0.0587(10) Uani 1 1 d . . .
C4 C 1.1715(8) 0.0627(5) 0.1183(4) 0.0951(16) Uani 1 1 d . . .
H2 H 1.2639 0.0603 0.0724 0.114 Uiso 1 1 calc R . .
C5 C 1.0657(7) 0.1430(4) 0.1306(3) 0.0798(13) Uani 1 1 d . . .
H14 H 1.0823 0.1952 0.0938 0.096 Uiso 1 1 calc R . .
C11 C 0.9017(10) 0.4367(4) 0.3634(4) 0.1064(18) Uani 1 1 d . . .
H5 H 0.9900 0.5085 0.3963 0.160 Uiso 1 1 calc R . .
H6 H 0.9404 0.3802 0.3884 0.160 Uiso 1 1 calc R . .
H7 H 0.7590 0.4339 0.3723 0.160 Uiso 1 1 calc R . .
C12 C 1.1542(9) 0.4210(4) 0.2431(4) 0.1047(18) Uani 1 1 d . . .
H10 H 1.2416 0.4949 0.2704 0.157 Uiso 1 1 calc R . .
H9 H 1.1662 0.4013 0.1760 0.157 Uiso 1 1 calc R . .
H8 H 1.1971 0.3694 0.2733 0.157 Uiso 1 1 calc R . .
C1 C 0.7091(7) 0.1680(4) 0.3002(3) 0.0705(11) Uani 1 1 d . . .
H13 H 0.6138 0.1984 0.3338 0.085 Uiso 1 1 calc R . .
N2 N 0.7629(5) 0.0797(3) 0.3143(2) 0.0655(9) Uani 1 1 d . . .
C14 C 0.560(2) 0.3278(7) -0.0724(7) 0.162(4) Uani 1 1 d . . .
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
S1 0.0717(7) 0.0721(7) 0.0635(7) 0.0084(5) -0.0030(5) 0.0120(5)
S2 0.0929(9) 0.0704(7) 0.0622(7) 0.0097(5) 0.0056(6) 0.0243(6)
O6 0.066(2) 0.169(4) 0.160(4) 0.012(3) 0.012(2) 0.040(2)
F6 0.085(2) 0.198(4) 0.139(3) -0.009(3) -0.025(2) 0.036(2)
F4 0.192(4) 0.159(3) 0.0560(18) 0.0081(19) 0.004(2) -0.013(3)
O4 0.190(4) 0.069(2) 0.109(3) 0.013(2) -0.032(3) 0.020(2)
O5 0.105(3) 0.125(3) 0.067(2) 0.0258(19) 0.0035(18) 0.034(2)
F5 0.186(4) 0.074(2) 0.139(3) 0.0022(19) -0.012(3) -0.003(2)
F1 0.413(11) 0.123(4) 0.197(6) -0.050(4) -0.118(6) 0.130(6)
F2 0.453(11) 0.146(4) 0.180(5) 0.071(4) -0.068(6) 0.120(5)
F3 0.227(7) 0.252(9) 0.448(15) 0.208(10) -0.042(9) -0.113(7)
C8 0.110(4) 0.069(3) 0.093(3) 0.017(3) -0.007(3) 0.027(3)
C7 0.120(4) 0.078(3) 0.069(3) 0.023(2) 0.034(3) 0.007(3)
O2 0.128(3) 0.147(3) 0.074(2) -0.024(2) -0.013(2) 0.070(3)
O1 0.112(3) 0.217(6) 0.133(4) 0.050(4) 0.039(3) 0.021(3)
O3 0.174(4) 0.110(3) 0.080(2) 0.003(2) -0.028(2) 0.068(3)
N3 0.074(2) 0.064(2) 0.068(2) 0.0068(17) 0.0015(18) 0.0156(18)
C3 0.089(4) 0.086(4) 0.096(4) -0.003(3) 0.015(3) 0.030(3)
C15 0.097(4) 0.081(3) 0.071(3) 0.005(2) 0.008(3) 0.010(3)
C13 0.168(6) 0.078(4) 0.118(5) 0.033(3) -0.019(4) 0.031(4)
C10 0.103(4) 0.062(3) 0.070(3) 0.017(2) -0.010(3) 0.013(2)
C9 0.089(3) 0.069(3) 0.070(3) 0.017(2) -0.011(2) 0.018(2)
N1 0.069(2) 0.0596(19) 0.0506(18) 0.0072(15) 0.0006(16) 0.0114(16)
C6 0.065(2) 0.061(2) 0.0417(19) 0.0040(16) 0.0025(17) 0.0057(19)
C2 0.062(2) 0.056(2) 0.049(2) 0.0004(17) 0.0013(18) 0.0088(18)
C4 0.089(4) 0.100(4) 0.085(3) 0.005(3) 0.033(3) 0.017(3)
C5 0.089(3) 0.079(3) 0.059(3) 0.009(2) 0.014(2) 0.005(3)
C11 0.161(5) 0.072(3) 0.072(3) 0.003(2) 0.000(3) 0.023(3)
C12 0.105(4) 0.082(3) 0.110(4) 0.024(3) -0.011(3) -0.002(3)
C1 0.075(3) 0.066(3) 0.060(2) 0.003(2) 0.010(2) 0.010(2)
N2 0.078(2) 0.058(2) 0.0537(18) 0.0077(15) 0.0133(17) 0.0084(17)
C14 0.249(12) 0.100(5) 0.119(6) 0.025(5) -0.037(7) 0.031(6)
_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
S1 O4 1.389(4) . ?
S1 O5 1.416(3) . ?
S1 O6 1.432(4) . ?
S1 C15 1.796(5) . ?
S2 O2 1.402(3) . ?
S2 O3 1.413(4) . ?
S2 O1 1.432(5) . ?
S2 C14 1.771(8) . ?
F6 C15 1.341(6) . ?
F4 C15 1.286(5) . ?
F5 C15 1.291(6) . ?
F1 C14 1.331(11) . ?
F2 C14 1.267(9) . ?
F3 C14 1.267(13) . ?
C8 N3 1.476(6) . ?
C8 H99A 0.9600 . ?
C8 H99B 0.9600 . ?
C8 H99C 0.9600 . ?
C7 N2 1.482(5) . ?
C7 H88A 0.9600 . ?
C7 H88B 0.9600 . ?
C7 H88C 0.9600 . ?
N3 C2 1.343(5) . ?
N3 C3 1.347(6) . ?
C3 C4 1.364(7) . ?
C3 H66 0.9300 . ?
C13 C10 1.530(7) . ?
C13 H1 0.9600 . ?
C13 H4 0.9600 . ?
C13 H3 0.9600 . ?
C10 C11 1.512(7) . ?
C10 C9 1.527(6) . ?
C10 C12 1.535(7) . ?
C9 N1 1.480(5) . ?
C9 H11 0.9700 . ?
C9 H12 0.9700 . ?
N1 C1 1.314(5) . ?
N1 C6 1.385(5) . ?
C6 C5 1.371(6) . ?
C6 C2 1.373(5) . ?
C2 N2 1.369(5) . ?
C4 C5 1.374(7) . ?
C4 H2 0.9300 . ?
C5 H14 0.9300 . ?
C11 H5 0.9600 . ?
C11 H6 0.9600 . ?
C11 H7 0.9600 . ?
C12 H10 0.9600 . ?
C12 H9 0.9600 . ?
C12 H8 0.9600 . ?
C1 N2 1.322(5) . ?
C1 H13 0.9300 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 S1 O5 113.5(3) . . ?
O4 S1 O6 115.0(3) . . ?
O5 S1 O6 114.1(3) . . ?
O4 S1 C15 104.7(3) . . ?
O5 S1 C15 104.7(2) . . ?
O6 S1 C15 103.3(3) . . ?
O2 S2 O3 116.3(2) . . ?
O2 S2 O1 110.9(3) . . ?
O3 S2 O1 115.8(3) . . ?
O2 S2 C14 104.7(4) . . ?
O3 S2 C14 105.3(4) . . ?
O1 S2 C14 101.9(5) . . ?
N3 C8 H99A 109.5 . . ?
N3 C8 H99B 109.5 . . ?
H99A C8 H99B 109.5 . . ?
N3 C8 H99C 109.5 . . ?
H99A C8 H99C 109.5 . . ?
H99B C8 H99C 109.5 . . ?
N2 C7 H88A 109.5 . . ?
N2 C7 H88B 109.5 . . ?
H88A C7 H88B 109.5 . . ?
N2 C7 H88C 109.5 . . ?
H88A C7 H88C 109.5 . . ?
H88B C7 H88C 109.5 . . ?
C2 N3 C3 116.8(4) . . ?
C2 N3 C8 124.5(4) . . ?
C3 N3 C8 118.7(4) . . ?
N3 C3 C4 122.8(5) . . ?
N3 C3 H66 118.6 . . ?
C4 C3 H66 118.6 . . ?
F4 C15 F5 107.9(4) . . ?
F4 C15 F6 108.7(5) . . ?
F5 C15 F6 104.5(5) . . ?
F4 C15 S1 112.5(4) . . ?
F5 C15 S1 112.9(4) . . ?
F6 C15 S1 109.9(3) . . ?
C10 C13 H1 109.5 . . ?
C10 C13 H4 109.5 . . ?
H1 C13 H4 109.5 . . ?
C10 C13 H3 109.5 . . ?
H1 C13 H3 109.5 . . ?
H4 C13 H3 109.5 . . ?
C11 C10 C9 111.4(4) . . ?
C11 C10 C13 109.7(4) . . ?
C9 C10 C13 105.3(4) . . ?
C11 C10 C12 109.9(4) . . ?
C9 C10 C12 110.7(4) . . ?
C13 C10 C12 109.8(4) . . ?
N1 C9 C10 114.5(3) . . ?
N1 C9 H11 108.6 . . ?
C10 C9 H11 108.6 . . ?
N1 C9 H12 108.6 . . ?
C10 C9 H12 108.6 . . ?
H11 C9 H12 107.6 . . ?
C1 N1 C6 107.2(3) . . ?
C1 N1 C9 125.0(4) . . ?
C6 N1 C9 127.8(3) . . ?
C5 C6 C2 121.7(4) . . ?
C5 C6 N1 132.3(4) . . ?
C2 C6 N1 106.0(3) . . ?
N3 C2 N2 129.8(4) . . ?
N3 C2 C6 121.8(4) . . ?
N2 C2 C6 108.4(4) . . ?
C3 C4 C5 121.1(5) . . ?
C3 C4 H2 119.5 . . ?
C5 C4 H2 119.5 . . ?
C6 C5 C4 115.8(5) . . ?
C6 C5 H14 122.1 . . ?
C4 C5 H14 122.1 . . ?
C10 C11 H5 109.5 . . ?
C10 C11 H6 109.5 . . ?
H5 C11 H6 109.5 . . ?
C10 C11 H7 109.5 . . ?
H5 C11 H7 109.5 . . ?
H6 C11 H7 109.5 . . ?
C10 C12 H10 109.5 . . ?
C10 C12 H9 109.5 . . ?
H10 C12 H9 109.5 . . ?
C10 C12 H8 109.5 . . ?
H10 C12 H8 109.5 . . ?
H9 C12 H8 109.5 . . ?
N1 C1 N2 112.2(4) . . ?
N1 C1 H13 123.9 . . ?
N2 C1 H13 123.9 . . ?
C1 N2 C2 106.3(3) . . ?
C1 N2 C7 122.3(4) . . ?
C2 N2 C7 131.4(4) . . ?
F3 C14 F2 111.0(10) . . ?
F3 C14 F1 106.0(9) . . ?
F2 C14 F1 109.1(10) . . ?
F3 C14 S2 109.8(9) . . ?
F2 C14 S2 112.7(7) . . ?
F1 C14 S2 107.9(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
C2 N3 C3 C4 -0.5(7) . . . . ?
C8 N3 C3 C4 177.5(5) . . . . ?
O4 S1 C15 F4 -60.8(5) . . . . ?
O5 S1 C15 F4 179.6(4) . . . . ?
O6 S1 C15 F4 59.9(5) . . . . ?
O4 S1 C15 F5 176.8(4) . . . . ?
O5 S1 C15 F5 57.1(5) . . . . ?
O6 S1 C15 F5 -62.5(5) . . . . ?
O4 S1 C15 F6 60.5(5) . . . . ?
O5 S1 C15 F6 -59.1(4) . . . . ?
O6 S1 C15 F6 -178.8(4) . . . . ?
C11 C10 C9 N1 -57.7(6) . . . . ?
C13 C10 C9 N1 -176.5(4) . . . . ?
C12 C10 C9 N1 64.9(5) . . . . ?
C10 C9 N1 C1 88.4(5) . . . . ?
C10 C9 N1 C6 -90.9(5) . . . . ?
C1 N1 C6 C5 178.6(4) . . . . ?
C9 N1 C6 C5 -2.0(7) . . . . ?
C1 N1 C6 C2 -0.4(4) . . . . ?
C9 N1 C6 C2 179.0(3) . . . . ?
C3 N3 C2 N2 179.7(4) . . . . ?
C8 N3 C2 N2 1.7(6) . . . . ?
C3 N3 C2 C6 -0.7(6) . . . . ?
C8 N3 C2 C6 -178.6(4) . . . . ?
C5 C6 C2 N3 1.9(6) . . . . ?
N1 C6 C2 N3 -179.0(3) . . . . ?
C5 C6 C2 N2 -178.4(4) . . . . ?
N1 C6 C2 N2 0.8(4) . . . . ?
N3 C3 C4 C5 0.6(8) . . . . ?
C2 C6 C5 C4 -1.7(6) . . . . ?
N1 C6 C5 C4 179.3(4) . . . . ?
C3 C4 C5 C6 0.6(7) . . . . ?
C6 N1 C1 N2 -0.1(5) . . . . ?
C9 N1 C1 N2 -179.5(3) . . . . ?
N1 C1 N2 C2 0.6(5) . . . . ?
N1 C1 N2 C7 180.0(4) . . . . ?
N3 C2 N2 C1 178.9(4) . . . . ?
C6 C2 N2 C1 -0.8(4) . . . . ?
N3 C2 N2 C7 -0.5(7) . . . . ?
C6 C2 N2 C7 179.8(4) . . . . ?
O2 S2 C14 F3 -72.3(8) . . . . ?
O3 S2 C14 F3 50.9(9) . . . . ?
O1 S2 C14 F3 172.1(8) . . . . ?
O2 S2 C14 F2 52.0(10) . . . . ?
O3 S2 C14 F2 175.2(8) . . . . ?
O1 S2 C14 F2 -63.6(10) . . . . ?
O2 S2 C14 F1 172.6(7) . . . . ?
O3 S2 C14 F1 -64.3(9) . . . . ?
O1 S2 C14 F1 57.0(8) . . . . ?
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max 0.365
_refine_diff_density_min -0.357
_refine_diff_density_rms 0.053
data_mo_hbp_67_1_0m_pf6a
_database_code_depnum_ccdc_archive 'CCDC 932702'
#TrackingRef '19247_web_deposit_cif_file_2_ChristianGanter_1365162269.Compound 9b.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C25 H40 Cl Ir N3, F6 P'
_chemical_formula_sum 'C25 H40 Cl F6 Ir N3 P'
_chemical_formula_weight 755.22
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'
Ir Ir -1.4442 7.9887 '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 21 21 21'
_symmetry_space_group_name_Hall 'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
_cell_length_a 11.8317(19)
_cell_length_b 11.9035(19)
_cell_length_c 20.770(3)
_cell_angle_alpha 90.00
_cell_angle_beta 90.00
_cell_angle_gamma 90.00
_cell_volume 2925.2(8)
_cell_formula_units_Z 4
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 9975
_cell_measurement_theta_min 2.427
_cell_measurement_theta_max 25.027
_exptl_crystal_description 'Long, slender prisms'
_exptl_crystal_colour orange
_exptl_crystal_size_max 0.65
_exptl_crystal_size_mid 0.25
_exptl_crystal_size_min 0.25
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.715
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1496
_exptl_absorpt_coefficient_mu 4.768
_exptl_absorpt_correction_type Multi-scan
_exptl_absorpt_correction_T_min 0.5600
_exptl_absorpt_correction_T_max 0.7452
_exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 296(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'microfocus sealed tube'
_diffrn_radiation_monochromator 'multilayers mirror'
_diffrn_measurement_device_type 'Bruker Kappa APEX II CCD area detector'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 20212
_diffrn_reflns_av_R_equivalents 0.0236
_diffrn_reflns_av_sigmaI/netI 0.0338
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -24
_diffrn_reflns_limit_l_max 23
_diffrn_reflns_theta_min 1.96
_diffrn_reflns_theta_max 25.08
_reflns_number_total 5066
_reflns_number_gt 4861
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'APEX2 (Bruker, 2006)'
_computing_cell_refinement 'SAINT (Bruker, 2006)'
_computing_data_reduction SAINT
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'ORTEP-3 (University of Glasgow, 2008)'
_computing_publication_material ?
_refine_special_details
;
The restraint command 'ISOR' was used to refine the non-H atom C10. The
other non-hydrogen atoms were refined with anisotropic temperature parameters.
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^)+(0.0158P)^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 mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack 0.012(5)
_refine_ls_number_reflns 5066
_refine_ls_number_parameters 341
_refine_ls_number_restraints 6
_refine_ls_R_factor_all 0.0200
_refine_ls_R_factor_gt 0.0184
_refine_ls_wR_factor_ref 0.0405
_refine_ls_wR_factor_gt 0.0401
_refine_ls_goodness_of_fit_ref 0.991
_refine_ls_restrained_S_all 1.000
_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
Ir1 Ir 0.318345(11) 0.446487(11) 0.788830(6) 0.02786(5) Uani 1 1 d . . .
Cl1 Cl 0.26896(10) 0.61333(8) 0.73483(5) 0.0453(3) Uani 1 1 d . . .
P1 P -0.34639(10) 0.41451(9) 1.03643(7) 0.0501(3) Uani 1 1 d . . .
F1 F -0.4386(3) 0.3755(3) 0.98650(18) 0.1066(13) Uani 1 1 d . . .
F2 F -0.2573(3) 0.4506(3) 1.0887(2) 0.1066(12) Uani 1 1 d . . .
F3 F -0.2733(3) 0.3049(2) 1.0210(2) 0.0995(12) Uani 1 1 d . . .
F4 F -0.2793(4) 0.4823(3) 0.9865(2) 0.1422(19) Uani 1 1 d . . .
F5 F -0.4201(2) 0.5216(2) 1.05312(16) 0.0787(9) Uani 1 1 d . . .
F6 F -0.4104(3) 0.3450(3) 1.08921(18) 0.1075(12) Uani 1 1 d . . .
N2 N 0.2640(3) 0.4943(3) 0.92873(15) 0.0313(7) Uani 1 1 d . . .
N3 N 0.1995(3) 0.4438(3) 1.03754(14) 0.0411(8) Uani 1 1 d . . .
N1 N 0.1149(2) 0.4328(3) 0.87646(14) 0.0309(7) Uani 1 1 d . . .
C23 C 0.4265(4) 0.3425(4) 0.8441(2) 0.0433(11) Uani 1 1 d . . .
H11 H 0.4091 0.3872 0.8795 0.052 Uiso 1 1 calc R . .
C22 C 0.3383(4) 0.2750(3) 0.8190(2) 0.0449(11) Uani 1 1 d . . .
H10 H 0.2676 0.2803 0.8382 0.054 Uiso 1 1 calc R . .
C21 C 0.3515(5) 0.1948(4) 0.7631(2) 0.0674(16) Uani 1 1 d . . .
H9 H 0.4262 0.1614 0.7652 0.081 Uiso 1 1 calc R . .
H8 H 0.2969 0.1347 0.7679 0.081 Uiso 1 1 calc R . .
C20 C 0.3368(5) 0.2455(4) 0.6991(2) 0.0764(17) Uani 1 1 d . . .
H7 H 0.2591 0.2344 0.6856 0.092 Uiso 1 1 calc R . .
H1 H 0.3850 0.2063 0.6688 0.092 Uiso 1 1 calc R . .
C19 C 0.3636(4) 0.3695(3) 0.6960(2) 0.0492(12) Uani 1 1 d . . .
H6 H 0.3095 0.4151 0.6766 0.059 Uiso 1 1 calc R . .
C18 C 0.4579(3) 0.4221(3) 0.7184(2) 0.0413(10) Uani 1 1 d . . .
H5 H 0.4612 0.4998 0.7141 0.050 Uiso 1 1 calc R . .
C25 C 0.5563(4) 0.3651(4) 0.7492(3) 0.0655(15) Uani 1 1 d . . .
H7A H 0.5668 0.2924 0.7289 0.079 Uiso 1 1 calc R . .
H7B H 0.6237 0.4093 0.7409 0.079 Uiso 1 1 calc R . .
C24 C 0.5452(4) 0.3487(5) 0.8191(2) 0.0656(15) Uani 1 1 d . . .
H3 H 0.5836 0.4100 0.8407 0.079 Uiso 1 1 calc R . .
H4 H 0.5840 0.2798 0.8307 0.079 Uiso 1 1 calc R . .
C1 C 0.2227(3) 0.4694(3) 0.86756(17) 0.0284(9) Uani 1 1 d . . .
C12 C 0.3594(3) 0.5734(3) 0.93678(19) 0.0371(10) Uani 1 1 d . . .
H22 H 0.4058 0.5704 0.8983 0.045 Uiso 1 1 calc R . .
H21 H 0.4055 0.5478 0.9725 0.045 Uiso 1 1 calc R . .
C13 C 0.3265(4) 0.6962(3) 0.94908(19) 0.0429(10) Uani 1 1 d . . .
C15 C 0.2401(5) 0.7344(4) 0.8991(3) 0.0803(18) Uani 1 1 d . . .
H13 H 0.2287 0.8140 0.9029 0.120 Uiso 1 1 calc R . .
H12 H 0.1697 0.6962 0.9064 0.120 Uiso 1 1 calc R . .
H14 H 0.2674 0.7171 0.8568 0.120 Uiso 1 1 calc R . .
C16 C 0.2782(5) 0.7169(4) 1.0158(2) 0.0746(17) Uani 1 1 d . . .
H17 H 0.3331 0.6964 1.0477 0.112 Uiso 1 1 calc R . .
H15 H 0.2112 0.6724 1.0215 0.112 Uiso 1 1 calc R . .
H16 H 0.2596 0.7950 1.0204 0.112 Uiso 1 1 calc R . .
C14 C 0.4341(5) 0.7639(5) 0.9426(3) 0.093(2) Uani 1 1 d . . .
H18 H 0.4666 0.7513 0.9009 0.140 Uiso 1 1 calc R . .
H19 H 0.4868 0.7412 0.9753 0.140 Uiso 1 1 calc R . .
H20 H 0.4172 0.8423 0.9476 0.140 Uiso 1 1 calc R . .
C2 C 0.1879(3) 0.4603(3) 0.97317(16) 0.0310(8) Uani 1 1 d . . .
C3 C 0.1086(4) 0.4075(3) 1.0709(2) 0.0448(11) Uani 1 1 d . . .
H36 H 0.1144 0.3987 1.1153 0.054 Uiso 1 1 calc R . .
C4 C 0.0095(4) 0.3835(4) 1.0417(2) 0.0499(12) Uani 1 1 d . . .
H23 H -0.0527 0.3644 1.0668 0.060 Uiso 1 1 calc R . .
C5 C -0.0018(3) 0.3868(3) 0.9753(2) 0.0412(10) Uani 1 1 d . . .
H24 H -0.0680 0.3644 0.9549 0.049 Uiso 1 1 calc R . .
C6 C 0.0902(3) 0.4249(3) 0.94140(18) 0.0322(9) Uani 1 1 d . . .
C7 C 0.0446(3) 0.3883(3) 0.82330(19) 0.0372(9) Uani 1 1 d . . .
H26 H 0.0108 0.3184 0.8375 0.045 Uiso 1 1 calc R . .
H25 H 0.0940 0.3708 0.7874 0.045 Uiso 1 1 calc R . .
C8 C -0.0503(3) 0.4648(4) 0.7984(2) 0.0486(11) Uani 1 1 d . . .
C9 C -0.0140(5) 0.5825(4) 0.7895(4) 0.108(3) Uani 1 1 d . . .
H28 H -0.0753 0.6255 0.7720 0.162 Uiso 1 1 calc R . .
H27 H 0.0491 0.5849 0.7604 0.162 Uiso 1 1 calc R . .
H29 H 0.0080 0.6136 0.8302 0.162 Uiso 1 1 calc R . .
C11 C -0.1527(4) 0.4640(6) 0.8425(3) 0.104(2) Uani 1 1 d . . .
H32 H -0.1328 0.4963 0.8833 0.157 Uiso 1 1 calc R . .
H30 H -0.1777 0.3881 0.8488 0.157 Uiso 1 1 calc R . .
H31 H -0.2124 0.5071 0.8234 0.157 Uiso 1 1 calc R . .
C10 C -0.0874(6) 0.4138(6) 0.7358(3) 0.115(3) Uani 1 1 d U . .
H33 H -0.1501 0.4556 0.7189 0.172 Uiso 1 1 calc R . .
H34 H -0.1098 0.3373 0.7428 0.172 Uiso 1 1 calc R . .
H35 H -0.0259 0.4159 0.7056 0.172 Uiso 1 1 calc R . .
C17 C 0.3128(4) 0.4436(4) 1.0689(2) 0.0594(12) Uani 1 1 d . . .
H38 H 0.3063 0.4133 1.1116 0.089 Uiso 1 1 calc R . .
H37 H 0.3411 0.5190 1.0712 0.089 Uiso 1 1 calc R . .
H39 H 0.3639 0.3982 1.0442 0.089 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
Ir1 0.02722(7) 0.03225(7) 0.02412(7) 0.00112(7) 0.00259(7) 0.00054(7)
Cl1 0.0592(7) 0.0413(6) 0.0354(6) 0.0090(4) 0.0038(5) 0.0068(5)
P1 0.0449(8) 0.0409(7) 0.0646(8) 0.0001(6) -0.0018(6) -0.0018(5)
F1 0.129(3) 0.083(2) 0.108(3) -0.028(2) -0.068(3) 0.019(2)
F2 0.081(2) 0.086(2) 0.153(3) -0.033(3) -0.052(2) 0.007(2)
F3 0.076(2) 0.0538(18) 0.169(4) -0.024(2) -0.001(2) 0.0113(15)
F4 0.181(5) 0.084(3) 0.162(4) 0.021(3) 0.109(4) -0.002(3)
F5 0.063(2) 0.0605(18) 0.112(3) -0.0150(17) -0.0079(18) 0.0123(14)
F6 0.133(3) 0.083(2) 0.107(3) 0.028(2) 0.024(3) -0.018(2)
N2 0.0314(18) 0.0354(17) 0.0270(18) -0.0010(14) 0.0055(14) -0.0009(14)
N3 0.044(2) 0.0506(18) 0.0283(17) 0.0023(17) 0.0052(15) 0.005(2)
N1 0.0257(16) 0.0419(19) 0.0251(16) 0.0009(15) 0.0017(13) -0.0012(15)
C23 0.046(3) 0.048(2) 0.035(2) 0.000(2) -0.004(2) 0.020(2)
C22 0.050(3) 0.040(2) 0.044(2) 0.0090(19) 0.007(2) 0.012(2)
C21 0.099(4) 0.036(3) 0.068(3) -0.005(2) -0.007(3) 0.004(2)
C20 0.111(5) 0.052(3) 0.066(4) -0.019(3) 0.027(4) -0.017(3)
C19 0.062(3) 0.047(3) 0.038(3) -0.007(2) 0.018(2) -0.007(2)
C18 0.037(2) 0.042(2) 0.045(2) 0.002(2) 0.022(2) 0.0012(18)
C25 0.042(3) 0.070(3) 0.085(4) 0.020(3) 0.020(3) 0.012(3)
C24 0.040(3) 0.102(4) 0.055(3) -0.015(3) -0.008(3) 0.030(3)
C1 0.0273(19) 0.031(2) 0.0273(19) 0.0021(16) -0.0026(16) 0.0067(14)
C12 0.032(2) 0.045(3) 0.035(2) -0.0031(19) 0.0048(17) -0.0093(18)
C13 0.052(3) 0.040(2) 0.036(2) -0.0058(17) 0.006(2) -0.005(2)
C15 0.120(5) 0.038(3) 0.082(4) -0.007(3) -0.020(4) 0.021(3)
C16 0.112(5) 0.051(3) 0.060(3) -0.016(3) 0.026(3) -0.004(3)
C14 0.078(4) 0.076(4) 0.125(6) -0.023(4) 0.039(4) -0.034(3)
C2 0.037(2) 0.0291(18) 0.0274(18) -0.0017(15) 0.0062(18) 0.000(2)
C3 0.058(3) 0.042(2) 0.034(2) 0.0043(19) 0.014(2) -0.002(2)
C4 0.050(3) 0.059(3) 0.041(3) 0.008(2) 0.023(2) 0.001(2)
C5 0.034(2) 0.047(2) 0.043(3) 0.006(2) 0.0085(19) -0.0029(19)
C6 0.030(2) 0.030(2) 0.036(2) 0.0013(17) 0.0084(18) 0.0039(16)
C7 0.034(2) 0.047(2) 0.030(2) 0.0034(18) -0.0014(19) -0.0041(19)
C8 0.035(2) 0.062(3) 0.049(3) 0.009(2) -0.006(2) -0.001(2)
C9 0.059(4) 0.068(4) 0.197(8) 0.047(5) -0.025(5) 0.004(3)
C11 0.048(3) 0.158(6) 0.107(5) 0.055(5) 0.009(3) 0.031(4)
C10 0.126(5) 0.137(5) 0.082(4) -0.016(4) -0.052(4) 0.037(4)
C17 0.054(3) 0.086(3) 0.038(2) 0.012(3) -0.005(2) -0.009(4)
_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
Ir1 C1 2.007(4) . ?
Ir1 C23 2.118(4) . ?
Ir1 C22 2.149(4) . ?
Ir1 C19 2.200(4) . ?
Ir1 C18 2.225(4) . ?
Ir1 Cl1 2.3545(10) . ?
P1 F4 1.536(4) . ?
P1 F6 1.568(4) . ?
P1 F2 1.573(3) . ?
P1 F1 1.575(3) . ?
P1 F5 1.583(3) . ?
P1 F3 1.598(3) . ?
N2 C2 1.352(5) . ?
N2 C1 1.393(5) . ?
N2 C12 1.479(5) . ?
N3 C3 1.350(5) . ?
N3 C2 1.358(4) . ?
N3 C17 1.491(5) . ?
N1 C1 1.361(5) . ?
N1 C6 1.383(5) . ?
N1 C7 1.480(5) . ?
C23 C22 1.416(6) . ?
C23 C24 1.500(6) . ?
C23 H11 0.9300 . ?
C22 C21 1.511(6) . ?
C22 H10 0.9300 . ?
C21 C20 1.469(6) . ?
C21 H9 0.9700 . ?
C21 H8 0.9700 . ?
C20 C19 1.511(6) . ?
C20 H7 0.9700 . ?
C20 H1 0.9700 . ?
C19 C18 1.361(6) . ?
C19 H6 0.9300 . ?
C18 C25 1.492(6) . ?
C18 H5 0.9300 . ?
C25 C24 1.472(6) . ?
C25 H7A 0.9700 . ?
C25 H7B 0.9700 . ?
C24 H3 0.9700 . ?
C24 H4 0.9700 . ?
C12 C13 1.534(5) . ?
C12 H22 0.9700 . ?
C12 H21 0.9700 . ?
C13 C14 1.514(6) . ?
C13 C16 1.519(6) . ?
C13 C15 1.526(7) . ?
C15 H13 0.9600 . ?
C15 H12 0.9600 . ?
C15 H14 0.9600 . ?
C16 H17 0.9600 . ?
C16 H15 0.9600 . ?
C16 H16 0.9600 . ?
C14 H18 0.9600 . ?
C14 H19 0.9600 . ?
C14 H20 0.9600 . ?
C2 C6 1.396(5) . ?
C3 C4 1.351(6) . ?
C3 H36 0.9300 . ?
C4 C5 1.385(6) . ?
C4 H23 0.9300 . ?
C5 C6 1.374(5) . ?
C5 H24 0.9300 . ?
C7 C8 1.535(5) . ?
C7 H26 0.9700 . ?
C7 H25 0.9700 . ?
C8 C9 1.477(6) . ?
C8 C10 1.502(7) . ?
C8 C11 1.519(7) . ?
C9 H28 0.9600 . ?
C9 H27 0.9600 . ?
C9 H29 0.9600 . ?
C11 H32 0.9600 . ?
C11 H30 0.9600 . ?
C11 H31 0.9600 . ?
C10 H33 0.9600 . ?
C10 H34 0.9600 . ?
C10 H35 0.9600 . ?
C17 H38 0.9600 . ?
C17 H37 0.9600 . ?
C17 H39 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
C1 Ir1 C23 88.75(15) . . ?
C1 Ir1 C22 87.33(15) . . ?
C23 Ir1 C22 38.75(16) . . ?
C1 Ir1 C19 155.15(15) . . ?
C23 Ir1 C19 94.85(17) . . ?
C22 Ir1 C19 80.40(16) . . ?
C1 Ir1 C18 166.35(15) . . ?
C23 Ir1 C18 80.34(16) . . ?
C22 Ir1 C18 89.21(15) . . ?
C19 Ir1 C18 35.82(15) . . ?
C1 Ir1 Cl1 97.69(10) . . ?
C23 Ir1 Cl1 154.30(13) . . ?
C22 Ir1 Cl1 165.40(12) . . ?
C19 Ir1 Cl1 89.66(12) . . ?
C18 Ir1 Cl1 88.90(10) . . ?
F4 P1 F6 177.6(3) . . ?
F4 P1 F2 88.6(3) . . ?
F6 P1 F2 89.1(2) . . ?
F4 P1 F1 93.9(3) . . ?
F6 P1 F1 88.3(2) . . ?
F2 P1 F1 177.4(2) . . ?
F4 P1 F5 90.54(19) . . ?
F6 P1 F5 90.31(19) . . ?
F2 P1 F5 89.89(18) . . ?
F1 P1 F5 89.97(17) . . ?
F4 P1 F3 90.8(2) . . ?
F6 P1 F3 88.4(2) . . ?
F2 P1 F3 89.96(19) . . ?
F1 P1 F3 90.12(19) . . ?
F5 P1 F3 178.7(2) . . ?
C2 N2 C1 109.0(3) . . ?
C2 N2 C12 128.5(3) . . ?
C1 N2 C12 120.4(3) . . ?
C3 N3 C2 118.1(4) . . ?
C3 N3 C17 119.4(3) . . ?
C2 N3 C17 121.4(3) . . ?
C1 N1 C6 110.6(3) . . ?
C1 N1 C7 122.7(3) . . ?
C6 N1 C7 125.8(3) . . ?
C22 C23 C24 126.2(4) . . ?
C22 C23 Ir1 71.8(2) . . ?
C24 C23 Ir1 110.4(3) . . ?
C22 C23 H11 116.9 . . ?
C24 C23 H11 116.9 . . ?
Ir1 C23 H11 87.7 . . ?
C23 C22 C21 124.4(4) . . ?
C23 C22 Ir1 69.5(2) . . ?
C21 C22 Ir1 112.8(3) . . ?
C23 C22 H10 117.8 . . ?
C21 C22 H10 117.8 . . ?
Ir1 C22 H10 87.7 . . ?
C20 C21 C22 115.0(4) . . ?
C20 C21 H9 108.5 . . ?
C22 C21 H9 108.5 . . ?
C20 C21 H8 108.5 . . ?
C22 C21 H8 108.5 . . ?
H9 C21 H8 107.5 . . ?
C21 C20 C19 114.5(4) . . ?
C21 C20 H7 108.6 . . ?
C19 C20 H7 108.6 . . ?
C21 C20 H1 108.6 . . ?
C19 C20 H1 108.6 . . ?
H7 C20 H1 107.6 . . ?
C18 C19 C20 127.3(5) . . ?
C18 C19 Ir1 73.1(2) . . ?
C20 C19 Ir1 108.5(3) . . ?
C18 C19 H6 116.3 . . ?
C20 C19 H6 116.3 . . ?
Ir1 C19 H6 88.3 . . ?
C19 C18 C25 125.3(4) . . ?
C19 C18 Ir1 71.1(2) . . ?
C25 C18 Ir1 110.9(3) . . ?
C19 C18 H5 117.4 . . ?
C25 C18 H5 117.4 . . ?
Ir1 C18 H5 87.9 . . ?
C24 C25 C18 114.4(4) . . ?
C24 C25 H7A 108.7 . . ?
C18 C25 H7A 108.7 . . ?
C24 C25 H7B 108.7 . . ?
C18 C25 H7B 108.7 . . ?
H7A C25 H7B 107.6 . . ?
C25 C24 C23 115.6(4) . . ?
C25 C24 H3 108.4 . . ?
C23 C24 H3 108.4 . . ?
C25 C24 H4 108.4 . . ?
C23 C24 H4 108.4 . . ?
H3 C24 H4 107.4 . . ?
N1 C1 N2 105.9(3) . . ?
N1 C1 Ir1 126.6(3) . . ?
N2 C1 Ir1 125.0(3) . . ?
N2 C12 C13 115.6(3) . . ?
N2 C12 H22 108.4 . . ?
C13 C12 H22 108.4 . . ?
N2 C12 H21 108.4 . . ?
C13 C12 H21 108.4 . . ?
H22 C12 H21 107.5 . . ?
C14 C13 C16 108.1(4) . . ?
C14 C13 C15 110.1(4) . . ?
C16 C13 C15 108.6(4) . . ?
C14 C13 C12 106.2(4) . . ?
C16 C13 C12 113.7(3) . . ?
C15 C13 C12 110.0(3) . . ?
C13 C15 H13 109.5 . . ?
C13 C15 H12 109.5 . . ?
H13 C15 H12 109.5 . . ?
C13 C15 H14 109.5 . . ?
H13 C15 H14 109.5 . . ?
H12 C15 H14 109.5 . . ?
C13 C16 H17 109.5 . . ?
C13 C16 H15 109.5 . . ?
H17 C16 H15 109.5 . . ?
C13 C16 H16 109.5 . . ?
H17 C16 H16 109.5 . . ?
H15 C16 H16 109.5 . . ?
C13 C14 H18 109.5 . . ?
C13 C14 H19 109.5 . . ?
H18 C14 H19 109.5 . . ?
C13 C14 H20 109.5 . . ?
H18 C14 H20 109.5 . . ?
H19 C14 H20 109.5 . . ?
N2 C2 N3 130.4(4) . . ?
N2 C2 C6 108.6(3) . . ?
N3 C2 C6 120.4(3) . . ?
N3 C3 C4 121.9(4) . . ?
N3 C3 H36 119.1 . . ?
C4 C3 H36 119.1 . . ?
C3 C4 C5 121.7(4) . . ?
C3 C4 H23 119.2 . . ?
C5 C4 H23 119.2 . . ?
C6 C5 C4 116.3(4) . . ?
C6 C5 H24 121.9 . . ?
C4 C5 H24 121.9 . . ?
C5 C6 N1 133.6(4) . . ?
C5 C6 C2 120.9(4) . . ?
N1 C6 C2 105.4(3) . . ?
N1 C7 C8 116.7(3) . . ?
N1 C7 H26 108.1 . . ?
C8 C7 H26 108.1 . . ?
N1 C7 H25 108.1 . . ?
C8 C7 H25 108.1 . . ?
H26 C7 H25 107.3 . . ?
C9 C8 C10 111.1(5) . . ?
C9 C8 C11 108.3(5) . . ?
C10 C8 C11 106.7(5) . . ?
C9 C8 C7 113.1(4) . . ?
C10 C8 C7 105.4(4) . . ?
C11 C8 C7 112.1(4) . . ?
C8 C9 H28 109.5 . . ?
C8 C9 H27 109.5 . . ?
H28 C9 H27 109.5 . . ?
C8 C9 H29 109.5 . . ?
H28 C9 H29 109.5 . . ?
H27 C9 H29 109.5 . . ?
C8 C11 H32 109.5 . . ?
C8 C11 H30 109.5 . . ?
H32 C11 H30 109.5 . . ?
C8 C11 H31 109.5 . . ?
H32 C11 H31 109.5 . . ?
H30 C11 H31 109.5 . . ?
C8 C10 H33 109.5 . . ?
C8 C10 H34 109.5 . . ?
H33 C10 H34 109.5 . . ?
C8 C10 H35 109.5 . . ?
H33 C10 H35 109.5 . . ?
H34 C10 H35 109.5 . . ?
N3 C17 H38 109.5 . . ?
N3 C17 H37 109.5 . . ?
H38 C17 H37 109.5 . . ?
N3 C17 H39 109.5 . . ?
H38 C17 H39 109.5 . . ?
H37 C17 H39 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
C1 Ir1 C23 C22 87.3(3) . . . . ?
C19 Ir1 C23 C22 -68.1(3) . . . . ?
C18 Ir1 C23 C22 -100.9(3) . . . . ?
Cl1 Ir1 C23 C22 -167.4(2) . . . . ?
C1 Ir1 C23 C24 -150.0(3) . . . . ?
C22 Ir1 C23 C24 122.7(4) . . . . ?
C19 Ir1 C23 C24 54.6(3) . . . . ?
C18 Ir1 C23 C24 21.8(3) . . . . ?
Cl1 Ir1 C23 C24 -44.7(5) . . . . ?
C24 C23 C22 C21 1.8(7) . . . . ?
Ir1 C23 C22 C21 104.2(4) . . . . ?
C24 C23 C22 Ir1 -102.4(4) . . . . ?
C1 Ir1 C22 C23 -91.3(3) . . . . ?
C19 Ir1 C22 C23 110.4(3) . . . . ?
C18 Ir1 C22 C23 75.5(3) . . . . ?
Cl1 Ir1 C22 C23 158.0(4) . . . . ?
C1 Ir1 C22 C21 148.8(4) . . . . ?
C23 Ir1 C22 C21 -119.8(5) . . . . ?
C19 Ir1 C22 C21 -9.5(4) . . . . ?
C18 Ir1 C22 C21 -44.4(4) . . . . ?
Cl1 Ir1 C22 C21 38.2(7) . . . . ?
C23 C22 C21 C20 -86.0(6) . . . . ?
Ir1 C22 C21 C20 -6.0(6) . . . . ?
C22 C21 C20 C19 26.5(7) . . . . ?
C21 C20 C19 C18 49.6(7) . . . . ?
C21 C20 C19 Ir1 -32.9(6) . . . . ?
C1 Ir1 C19 C18 -163.6(3) . . . . ?
C23 Ir1 C19 C18 -66.1(3) . . . . ?
C22 Ir1 C19 C18 -102.2(3) . . . . ?
Cl1 Ir1 C19 C18 88.6(2) . . . . ?
C1 Ir1 C19 C20 -39.1(6) . . . . ?
C23 Ir1 C19 C20 58.4(4) . . . . ?
C22 Ir1 C19 C20 22.4(4) . . . . ?
C18 Ir1 C19 C20 124.5(5) . . . . ?
Cl1 Ir1 C19 C20 -146.9(4) . . . . ?
C20 C19 C18 C25 2.0(7) . . . . ?
Ir1 C19 C18 C25 102.7(4) . . . . ?
C20 C19 C18 Ir1 -100.7(4) . . . . ?
C1 Ir1 C18 C19 149.9(6) . . . . ?
C23 Ir1 C18 C19 112.5(3) . . . . ?
C22 Ir1 C18 C19 74.6(3) . . . . ?
Cl1 Ir1 C18 C19 -90.9(3) . . . . ?
C1 Ir1 C18 C25 28.4(8) . . . . ?
C23 Ir1 C18 C25 -9.0(3) . . . . ?
C22 Ir1 C18 C25 -46.9(3) . . . . ?
C19 Ir1 C18 C25 -121.5(4) . . . . ?
Cl1 Ir1 C18 C25 147.6(3) . . . . ?
C19 C18 C25 C24 -87.2(6) . . . . ?
Ir1 C18 C25 C24 -6.1(6) . . . . ?
C18 C25 C24 C23 25.8(7) . . . . ?
C22 C23 C24 C25 49.0(7) . . . . ?
Ir1 C23 C24 C25 -32.9(6) . . . . ?
C6 N1 C1 N2 -5.1(4) . . . . ?
C7 N1 C1 N2 -174.5(3) . . . . ?
C6 N1 C1 Ir1 157.5(3) . . . . ?
C7 N1 C1 Ir1 -12.0(5) . . . . ?
C2 N2 C1 N1 7.4(4) . . . . ?
C12 N2 C1 N1 -157.3(3) . . . . ?
C2 N2 C1 Ir1 -155.5(2) . . . . ?
C12 N2 C1 Ir1 39.8(4) . . . . ?
C23 Ir1 C1 N1 -113.4(3) . . . . ?
C22 Ir1 C1 N1 -74.6(3) . . . . ?
C19 Ir1 C1 N1 -14.5(6) . . . . ?
C18 Ir1 C1 N1 -150.1(5) . . . . ?
Cl1 Ir1 C1 N1 91.6(3) . . . . ?
C23 Ir1 C1 N2 46.0(3) . . . . ?
C22 Ir1 C1 N2 84.7(3) . . . . ?
C19 Ir1 C1 N2 144.9(4) . . . . ?
C18 Ir1 C1 N2 9.2(8) . . . . ?
Cl1 Ir1 C1 N2 -109.0(3) . . . . ?
C2 N2 C12 C13 -67.9(5) . . . . ?
C1 N2 C12 C13 93.5(4) . . . . ?
N2 C12 C13 C14 -169.1(4) . . . . ?
N2 C12 C13 C16 72.1(5) . . . . ?
N2 C12 C13 C15 -50.0(5) . . . . ?
C1 N2 C2 N3 163.8(4) . . . . ?
C12 N2 C2 N3 -33.1(6) . . . . ?
C1 N2 C2 C6 -6.9(4) . . . . ?
C12 N2 C2 C6 156.2(3) . . . . ?
C3 N3 C2 N2 -179.0(4) . . . . ?
C17 N3 C2 N2 -10.9(6) . . . . ?
C3 N3 C2 C6 -9.3(5) . . . . ?
C17 N3 C2 C6 158.9(4) . . . . ?
C2 N3 C3 C4 2.5(6) . . . . ?
C17 N3 C3 C4 -165.9(4) . . . . ?
N3 C3 C4 C5 5.0(7) . . . . ?
C3 C4 C5 C6 -5.4(7) . . . . ?
C4 C5 C6 N1 174.5(4) . . . . ?
C4 C5 C6 C2 -1.4(6) . . . . ?
C1 N1 C6 C5 -175.4(4) . . . . ?
C7 N1 C6 C5 -6.3(7) . . . . ?
C1 N1 C6 C2 1.0(4) . . . . ?
C7 N1 C6 C2 170.1(3) . . . . ?
N2 C2 C6 C5 -179.4(3) . . . . ?
N3 C2 C6 C5 8.8(5) . . . . ?
N2 C2 C6 N1 3.7(4) . . . . ?
N3 C2 C6 N1 -168.1(3) . . . . ?
C1 N1 C7 C8 -106.0(4) . . . . ?
C6 N1 C7 C8 86.1(5) . . . . ?
N1 C7 C8 C9 44.6(6) . . . . ?
N1 C7 C8 C10 166.1(4) . . . . ?
N1 C7 C8 C11 -78.2(5) . . . . ?
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full 25.08
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max 0.507
_refine_diff_density_min -0.275
_refine_diff_density_rms 0.063