data_2006src0966p-1
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C16 H25 Cl3 N5 P3'
_chemical_formula_weight          486.67
 
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'
 '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'
 
_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                    9.4791(2)
_cell_length_b                    10.2283(2)
_cell_length_c                    11.4144(3)
_cell_angle_alpha                 88.423(2)
_cell_angle_beta                  78.172(2)
_cell_angle_gamma                 79.694(2)
_cell_volume                      1065.66(4)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     4117
_cell_measurement_theta_min       1.0
_cell_measurement_theta_max       26.02
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.28
_exptl_crystal_size_mid           0.21
_exptl_crystal_size_min           0.14
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.517
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              504
_exptl_absorpt_coefficient_mu     0.668
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.8349
_exptl_absorpt_correction_T_max   0.9122
_exptl_absorpt_process_details    'SADABS V2.10 (Sheldrick, G.M., 2003)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Bruker-Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          none
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         negligible
_diffrn_reflns_number             16626
_diffrn_reflns_av_R_equivalents   0.0250
_diffrn_reflns_av_sigmaI/netI     0.0231
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          3.27
_diffrn_reflns_theta_max          26.04
_reflns_number_total              4189
_reflns_number_gt                 3748
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_computing_cell_refinement        'DENZO, COLLECT'
_computing_data_reduction         'DENZO, COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material   ?
 
_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)+(0.0340P)²+1.1696P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          4189
_refine_ls_number_parameters      244
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0368
_refine_ls_R_factor_gt            0.0316
_refine_ls_wR_factor_ref          0.0818
_refine_ls_wR_factor_gt           0.0787
_refine_ls_goodness_of_fit_ref    1.050
_refine_ls_restrained_S_all       1.050
_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
C1 C 0.4624(2) 1.05198(18) 0.75816(17) 0.0167(4) Uani 1 1 d . . .
C2 C 0.4890(2) 1.1258(2) 0.85075(18) 0.0218(4) Uani 1 1 d . . .
H2 H 0.5063 1.0830 0.9227 0.026 Uiso 1 1 calc R . .
C3 C 0.4901(2) 1.2604(2) 0.83758(19) 0.0230(4) Uani 1 1 d . . .
H3 H 0.5055 1.3105 0.9012 0.028 Uiso 1 1 calc R . .
C4 C 0.4684(2) 1.3226(2) 0.73091(19) 0.0231(4) Uani 1 1 d . . .
H4 H 0.4723 1.4145 0.7210 0.028 Uiso 1 1 calc R . .
C5 C 0.4414(2) 1.2509(2) 0.63944(18) 0.0218(4) Uani 1 1 d . . .
H5 H 0.4229 1.2943 0.5681 0.026 Uiso 1 1 calc R . .
C6 C 0.4412(2) 1.1153(2) 0.65187(18) 0.0207(4) Uani 1 1 d . . .
H6 H 0.4266 1.0656 0.5876 0.025 Uiso 1 1 calc R . .
C7 C 0.7594(2) 0.8535(2) 0.70598(19) 0.0236(4) Uani 1 1 d . . .
H7A H 0.8393 0.8536 0.7499 0.028 Uiso 1 1 calc R . .
H7B H 0.7313 0.9449 0.6776 0.028 Uiso 1 1 calc R . .
C8 C 0.8151(3) 0.7600(2) 0.5985(2) 0.0305(5) Uani 1 1 d . . .
H8A H 0.7395 0.7674 0.5491 0.037 Uiso 1 1 calc R . .
H8B H 0.9040 0.7860 0.5486 0.037 Uiso 1 1 calc R . .
C9 C 0.8506(3) 0.6180(2) 0.6382(2) 0.0388(6) Uani 1 1 d . . .
H9A H 0.9342 0.6080 0.6793 0.047 Uiso 1 1 calc R . .
H9B H 0.8792 0.5581 0.5674 0.047 Uiso 1 1 calc R . .
C10 C 0.7174(3) 0.5795(2) 0.7232(3) 0.0383(6) Uani 1 1 d . . .
H10A H 0.6375 0.5794 0.6792 0.046 Uiso 1 1 calc R . .
H10B H 0.7440 0.4886 0.7534 0.046 Uiso 1 1 calc R . .
C11 C 0.6644(2) 0.6769(2) 0.8282(2) 0.0263(5) Uani 1 1 d . . .
H11A H 0.5751 0.6532 0.8795 0.032 Uiso 1 1 calc R . .
H11B H 0.7406 0.6694 0.8769 0.032 Uiso 1 1 calc R . .
C12 C -0.0512(2) 0.7902(2) 1.0385(2) 0.0276(5) Uani 1 1 d . . .
H12A H -0.0589 0.7458 0.9647 0.033 Uiso 1 1 calc R . .
H12B H -0.1340 0.8657 1.0566 0.033 Uiso 1 1 calc R . .
C13 C -0.0621(3) 0.6922(2) 1.1416(2) 0.0329(5) Uani 1 1 d . . .
H13A H 0.0113 0.6105 1.1186 0.039 Uiso 1 1 calc R . .
H13B H -0.1604 0.6673 1.1580 0.039 Uiso 1 1 calc R . .
C14 C -0.0358(3) 0.7524(2) 1.2548(2) 0.0311(5) Uani 1 1 d . . .
H14A H -0.0342 0.6841 1.3179 0.037 Uiso 1 1 calc R . .
H14B H -0.1171 0.8264 1.2843 0.037 Uiso 1 1 calc R . .
C15 C 0.1093(2) 0.8038(2) 1.22980(19) 0.0265(5) Uani 1 1 d . . .
H15A H 0.1196 0.8495 1.3021 0.032 Uiso 1 1 calc R . .
H15B H 0.1916 0.7280 1.2111 0.032 Uiso 1 1 calc R . .
C16 C 0.1161(2) 0.89994(19) 1.12532(18) 0.0207(4) Uani 1 1 d . . .
H16A H 0.0426 0.9814 1.1487 0.025 Uiso 1 1 calc R . .
H16B H 0.2141 0.9256 1.1065 0.025 Uiso 1 1 calc R . .
N1 N 0.35667(17) 0.85163(16) 0.90178(14) 0.0169(3) Uani 1 1 d . . .
N2 N 0.15408(18) 0.77838(17) 0.78939(15) 0.0213(4) Uani 1 1 d . . .
N3 N 0.41642(19) 0.82314(16) 0.66022(15) 0.0199(4) Uani 1 1 d . . .
N4 N 0.63181(18) 0.81439(17) 0.78843(15) 0.0212(4) Uani 1 1 d . . .
N5 N 0.08811(17) 0.84101(16) 1.01789(14) 0.0177(3) Uani 1 1 d . . .
P1 P 0.46223(5) 0.87800(5) 0.77708(4) 0.01623(12) Uani 1 1 d . . .
P2 P 0.22013(5) 0.78215(5) 0.90747(4) 0.01555(12) Uani 1 1 d . . .
P3 P 0.26120(6) 0.78794(5) 0.66520(4) 0.01815(12) Uani 1 1 d . . .
Cl1 Cl 0.28658(6) 0.58256(5) 0.94473(5) 0.02616(13) Uani 1 1 d . . .
Cl2 Cl 0.28493(6) 0.61830(5) 0.57130(5) 0.03081(14) Uani 1 1 d . . .
Cl3 Cl 0.15126(6) 0.91633(6) 0.56331(5) 0.03053(14) Uani 1 1 d . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 C6 1.393(3) . ?
C1 C2 1.404(3) . ?
C1 P1 1.7869(19) . ?
C2 C3 1.383(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N4 1.481(3) . ?
C7 C8 1.522(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.509(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.532(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.524(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N4 1.465(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 N5 1.476(2) . ?
C12 C13 1.524(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.529(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.530(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.523(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N5 1.473(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
N1 P2 1.5738(16) . ?
N1 P1 1.6098(16) . ?
N2 P3 1.5773(17) . ?
N2 P2 1.6023(17) . ?
N3 P3 1.5659(17) . ?
N3 P1 1.6274(17) . ?
N4 P1 1.6524(17) . ?
N5 P2 1.6256(16) . ?
P2 Cl1 2.0850(7) . ?
P3 Cl2 2.0184(7) . ?
P3 Cl3 2.0214(7) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C6 C1 C2 119.21(18) . . ?
C6 C1 P1 121.34(15) . . ?
C2 C1 P1 119.41(15) . . ?
C3 C2 C1 120.24(19) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.96(19) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.20(19) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.05(19) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.27(18) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
N4 C7 C8 112.05(17) . . ?
N4 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
N4 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C7 110.86(19) . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C8 C9 C10 110.15(19) . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C9 110.50(19) . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N4 C11 C10 111.98(18) . . ?
N4 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
N4 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
N5 C12 C13 111.74(18) . . ?
N5 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
N5 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 C14 111.09(19) . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 110.94(18) . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C14 110.86(18) . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
N5 C16 C15 111.83(16) . . ?
N5 C16 H16A 109.2 . . ?
C15 C16 H16A 109.2 . . ?
N5 C16 H16B 109.3 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
P2 N1 P1 122.19(10) . . ?
P3 N2 P2 117.13(11) . . ?
P3 N3 P1 122.00(11) . . ?
C11 N4 C7 111.73(16) . . ?
C11 N4 P1 119.03(14) . . ?
C7 N4 P1 121.45(14) . . ?
C16 N5 C12 113.73(16) . . ?
C16 N5 P2 121.89(13) . . ?
C12 N5 P2 119.85(14) . . ?
N1 P1 N3 113.79(9) . . ?
N1 P1 N4 107.36(9) . . ?
N3 P1 N4 112.88(9) . . ?
N1 P1 C1 110.16(9) . . ?
N3 P1 C1 107.88(9) . . ?
N4 P1 C1 104.36(9) . . ?
N1 P2 N2 118.79(9) . . ?
N1 P2 N5 111.04(9) . . ?
N2 P2 N5 108.75(9) . . ?
N1 P2 Cl1 106.63(6) . . ?
N2 P2 Cl1 104.17(7) . . ?
N5 P2 Cl1 106.57(6) . . ?
N3 P3 N2 120.34(9) . . ?
N3 P3 Cl2 108.61(7) . . ?
N2 P3 Cl2 109.13(7) . . ?
N3 P3 Cl3 109.72(7) . . ?
N2 P3 Cl3 107.25(7) . . ?
Cl2 P3 Cl3 99.85(3) . . ?
 
_diffrn_measured_fraction_theta_max    0.993
_diffrn_reflns_theta_full              26.04
_diffrn_measured_fraction_theta_full   0.993
_refine_diff_density_max    0.557
_refine_diff_density_min   -0.527
_refine_diff_density_rms    0.065
