data_2007src0259
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C18 H25 Cl N5 O2 P3'
_chemical_formula_weight          471.79
 
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'
 '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            Monoclinic
_symmetry_space_group_name_H-M    P2(1)
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z'
 
_cell_length_a                    9.7832(2)
_cell_length_b                    10.0420(2)
_cell_length_c                    11.5984(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  109.2280(10)
_cell_angle_gamma                 90.00
_cell_volume                      1075.90(4)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     9129
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        prism
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.30
_exptl_crystal_size_mid           0.20
_exptl_crystal_size_min           0.20
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.456
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              492
_exptl_absorpt_coefficient_mu     0.426
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.8827
_exptl_absorpt_correction_T_max   0.9196
_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             15393
_diffrn_reflns_av_R_equivalents   0.0237
_diffrn_reflns_av_sigmaI/netI     0.0270
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -14
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_theta_min          3.00
_diffrn_reflns_theta_max          27.49
_reflns_number_total              4883
_reflns_number_gt                 4795
_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)+(0.0752P)²+0.5374P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    0.51(6)
_refine_ls_number_reflns          4883
_refine_ls_number_parameters      281
_refine_ls_number_restraints      7
_refine_ls_R_factor_all           0.0348
_refine_ls_R_factor_gt            0.0340
_refine_ls_wR_factor_ref          0.1012
_refine_ls_wR_factor_gt           0.1002
_refine_ls_goodness_of_fit_ref    1.018
_refine_ls_restrained_S_all       1.017
_refine_ls_shift/su_max           0.227
_refine_ls_shift/su_mean          0.009
 
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 0.2688(3) 0.4122(2) 0.9245(2) 0.0187(5) Uani 1 1 d . . .
H1A H 0.2380 0.3514 0.9785 0.022 Uiso 1 1 calc R . .
H1B H 0.1917 0.4120 0.8437 0.022 Uiso 1 1 calc R . .
C2 C 0.2820(3) 0.5529(3) 0.9774(2) 0.0205(5) Uani 1 1 d . . .
H2A H 0.1980 0.5687 1.0052 0.025 Uiso 1 1 calc R . .
H2B H 0.3700 0.5562 1.0505 0.025 Uiso 1 1 calc R . .
C3 C 0.2899(3) 0.6676(2) 0.8935(2) 0.0179(5) Uani 1 1 d . . .
H3A H 0.2168 0.6538 0.8119 0.021 Uiso 1 1 calc R . .
H3B H 0.2668 0.7522 0.9269 0.021 Uiso 1 1 calc R . .
C4 C 0.4341(4) 0.8745(3) 0.6603(4) 0.0490(10) Uani 1 1 d . . .
H4A H 0.4794 0.9024 0.7464 0.059 Uiso 1 1 calc R A 1
H4B H 0.3515 0.9347 0.6216 0.059 Uiso 1 1 calc R A 1
C5 C 0.5569(4) 0.8856(5) 0.5857(4) 0.0433(16) Uani 0.719(8) 1 d P B 1
H5A H 0.6402 0.8265 0.6255 0.052 Uiso 0.719(8) 1 calc PR B 1
H5B H 0.5120 0.8556 0.5002 0.052 Uiso 0.719(8) 1 calc PR B 1
C5' C 0.5597(7) 0.9394(7) 0.6783(6) 0.0058(18) Uani 0.281(8) 1 d PU B 2
H5'1 H 0.6360 0.8713 0.7099 0.007 Uiso 0.281(8) 1 calc PR B 2
H5'2 H 0.5689 1.0008 0.7473 0.007 Uiso 0.281(8) 1 calc PR B 2
C6 C 0.6068(5) 1.0204(4) 0.5872(4) 0.0536(10) Uani 1 1 d . . .
H6A H 0.5291 1.0770 0.5333 0.064 Uiso 1 1 calc R B 1
H6B H 0.6357 1.0570 0.6710 0.064 Uiso 1 1 calc R B 1
C7 C 0.8034(2) 0.4457(3) 0.70953(19) 0.0148(4) Uani 1 1 d . B .
C8 C 0.8625(3) 0.5578(3) 0.6722(3) 0.0263(6) Uani 1 1 d . . .
H8 H 0.8449 0.6441 0.6978 0.032 Uiso 1 1 calc R . .
C9 C 0.9471(3) 0.5426(4) 0.5976(3) 0.0370(7) Uani 1 1 d . . .
H9 H 0.9866 0.6191 0.5721 0.044 Uiso 1 1 calc R . .
C10 C 0.9744(3) 0.4189(4) 0.5600(2) 0.0349(8) Uani 1 1 d . . .
H10 H 1.0335 0.4097 0.5099 0.042 Uiso 1 1 calc R . .
C11 C 0.9153(3) 0.3074(4) 0.5957(2) 0.0310(7) Uani 1 1 d . . .
H11 H 0.9334 0.2217 0.5691 0.037 Uiso 1 1 calc R . .
C12 C 0.8292(3) 0.3198(3) 0.6704(2) 0.0212(5) Uani 1 1 d . . .
H12 H 0.7886 0.2430 0.6944 0.025 Uiso 1 1 calc R . .
C13 C 0.8346(2) 0.4576(2) 0.96388(19) 0.0122(4) Uani 1 1 d . B .
C14 C 0.9464(2) 0.3644(3) 0.9915(2) 0.0164(4) Uani 1 1 d . . .
H14 H 0.9578 0.3092 0.9288 0.020 Uiso 1 1 calc R . .
C15 C 1.0413(2) 0.3519(3) 1.1102(2) 0.0217(5) Uani 1 1 d . . .
H15 H 1.1172 0.2882 1.1283 0.026 Uiso 1 1 calc R . .
C16 C 1.0255(3) 0.4326(3) 1.2024(2) 0.0269(6) Uani 1 1 d . . .
H16 H 1.0909 0.4246 1.2834 0.032 Uiso 1 1 calc R . .
C17 C 0.9138(3) 0.5250(3) 1.1757(2) 0.0295(6) Uani 1 1 d . . .
H17 H 0.9022 0.5796 1.2387 0.035 Uiso 1 1 calc R . .
C18 C 0.8182(3) 0.5377(3) 1.0562(2) 0.0220(5) Uani 1 1 d . . .
H18 H 0.7420 0.6011 1.0381 0.026 Uiso 1 1 calc R . .
N1 N 0.36099(19) 0.49478(19) 0.70932(16) 0.0111(3) Uani 1 1 d . B .
N2 N 0.6268(2) 0.60951(19) 0.79362(18) 0.0135(4) Uani 1 1 d . B .
N3 N 0.5982(2) 0.33554(18) 0.79820(18) 0.0131(4) Uani 1 1 d . B .
N4 N 0.4030(2) 0.3598(2) 0.90989(19) 0.0166(4) Uani 1 1 d . . .
N5 N 0.3831(2) 0.7394(2) 0.6559(2) 0.0165(4) Uani 1 1 d . B .
O1 O 0.43306(17) 0.67723(16) 0.88124(14) 0.0139(3) Uani 1 1 d . B .
O2 O 0.7212(3) 1.0175(3) 0.54699(18) 0.0461(7) Uani 1 1 d . B .
H2 H 0.6985 0.9769 0.4800 0.069 Uiso 1 1 calc R . .
P1 P 0.43341(5) 0.36272(5) 0.78036(5) 0.01014(13) Uani 1 1 d . B .
P2 P 0.45595(6) 0.62596(5) 0.75840(5) 0.00930(12) Uani 1 1 d . . .
P3 P 0.70166(6) 0.46483(5) 0.81287(5) 0.01032(13) Uani 1 1 d . . .
Cl1 Cl 0.31959(6) 0.21212(6) 0.67400(6) 0.02193(14) Uani 1 1 d . . .
H5N H 0.349(4) 0.708(4) 0.587(3) 0.032(9) Uiso 1 1 d . . .
H4N H 0.449(4) 0.304(4) 0.957(3) 0.024(8) Uiso 1 1 d . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 N4 1.476(3) . ?
C1 C2 1.529(3) . ?
C2 C3 1.526(3) . ?
C3 O1 1.457(3) . ?
C4 C5' 1.346(7) . ?
C4 N5 1.441(4) . ?
C4 C5 1.701(6) . ?
C5 C6 1.437(7) . ?
C5' C6 1.520(8) . ?
C6 O2 1.347(5) . ?
C7 C12 1.394(4) . ?
C7 C8 1.397(4) . ?
C7 P3 1.803(2) . ?
C8 C9 1.389(4) . ?
C9 C10 1.372(5) . ?
C10 C11 1.384(5) . ?
C11 C12 1.400(3) . ?
C13 C18 1.389(3) . ?
C13 C14 1.395(3) . ?
C13 P3 1.807(2) . ?
C14 C15 1.389(3) . ?
C15 C16 1.391(4) . ?
C16 C17 1.388(4) . ?
C17 C18 1.399(4) . ?
N1 P1 1.5984(19) . ?
N1 P2 1.6044(19) . ?
N2 P2 1.5931(19) . ?
N2 P3 1.609(2) . ?
N3 P1 1.5800(19) . ?
N3 P3 1.6204(19) . ?
N4 P1 1.625(2) . ?
N5 P2 1.631(2) . ?
O1 P2 1.5985(16) . ?
P1 Cl1 2.0357(8) . ?
P1 P2 2.6718(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
N4 C1 C2 114.5(2) . . ?
C3 C2 C1 117.2(2) . . ?
O1 C3 C2 111.36(19) . . ?
C5' C4 N5 138.6(4) . . ?
C5' C4 C5 44.3(3) . . ?
N5 C4 C5 109.8(3) . . ?
C6 C5 C4 110.5(3) . . ?
C4 C5' C6 128.5(5) . . ?
O2 C6 C5 107.1(4) . . ?
O2 C6 C5' 134.9(4) . . ?
C5 C6 C5' 47.5(4) . . ?
C12 C7 C8 119.5(2) . . ?
C12 C7 P3 120.74(18) . . ?
C8 C7 P3 119.7(2) . . ?
C9 C8 C7 119.8(3) . . ?
C10 C9 C8 121.0(3) . . ?
C9 C10 C11 119.6(2) . . ?
C10 C11 C12 120.6(3) . . ?
C7 C12 C11 119.5(3) . . ?
C18 C13 C14 119.5(2) . . ?
C18 C13 P3 119.68(17) . . ?
C14 C13 P3 120.63(17) . . ?
C15 C14 C13 120.4(2) . . ?
C14 C15 C16 120.1(2) . . ?
C17 C16 C15 119.8(2) . . ?
C16 C17 C18 120.1(2) . . ?
C13 C18 C17 120.1(2) . . ?
P1 N1 P2 113.06(10) . . ?
P2 N2 P3 121.36(12) . . ?
P1 N3 P3 116.78(12) . . ?
C1 N4 P1 122.71(17) . . ?
C4 N5 P2 124.6(2) . . ?
C3 O1 P2 119.13(14) . . ?
N3 P1 N1 118.09(10) . . ?
N3 P1 N4 111.43(11) . . ?
N1 P1 N4 107.86(11) . . ?
N3 P1 Cl1 106.38(8) . . ?
N1 P1 Cl1 104.05(7) . . ?
N4 P1 Cl1 108.45(9) . . ?
N3 P1 P2 94.05(7) . . ?
N1 P1 P2 33.54(7) . . ?
N4 P1 P2 98.75(8) . . ?
Cl1 P1 P2 136.31(3) . . ?
N2 P2 O1 104.36(9) . . ?
N2 P2 N1 116.22(10) . . ?
O1 P2 N1 110.24(9) . . ?
N2 P2 N5 115.42(11) . . ?
O1 P2 N5 105.59(10) . . ?
N1 P2 N5 104.58(11) . . ?
N2 P2 P1 89.17(7) . . ?
O1 P2 P1 101.16(6) . . ?
N1 P2 P1 33.40(6) . . ?
N5 P2 P1 136.92(8) . . ?
N2 P3 N3 117.95(10) . . ?
N2 P3 C7 109.24(11) . . ?
N3 P3 C7 107.92(11) . . ?
N2 P3 C13 108.67(11) . . ?
N3 P3 C13 107.16(10) . . ?
C7 P3 C13 105.16(10) . . ?
 
_diffrn_measured_fraction_theta_max    0.992
_diffrn_reflns_theta_full              27.49
_diffrn_measured_fraction_theta_full   0.992
_refine_diff_density_max    1.216
_refine_diff_density_min   -0.519
_refine_diff_density_rms    0.068
