data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 Mimi Hii
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C22 H28 N O2 P'
_chemical_formula_weight          369.42
_chemical_absolute_configuration  unk
 
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'
 
_symmetry_cell_setting            Orthorhombic
_symmetry_space_group_name_H-M    P2(1)2(1)2(1)
_symmetry_space_group_name_hall   'P 2ac 2ab'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    9.7279(2)
_cell_length_b                    10.2527(2)
_cell_length_c                    20.2703(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      2021.70(7)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     2453
_cell_measurement_theta_min       2.910
_cell_measurement_theta_max       27.485
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.18
_exptl_crystal_size_mid           0.18
_exptl_crystal_size_min           0.12
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.214
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              792
_exptl_absorpt_coefficient_mu     0.151
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9733
_exptl_absorpt_correction_T_max   0.9821
_exptl_absorpt_process_details    'SORTAV Blessing (1997)'
_exptl_special_details
;
 PLEASE NOTE cell_measurement_ fields are not relevant to area detector data,
 the entire data set is used to refine the cell, which is indexed from all
 observed reflections in a 10 degree phi range.
;
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'φ and ω scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             9715
_diffrn_reflns_av_R_equivalents   0.0467
_diffrn_reflns_av_sigmaI/netI     0.0593
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -24
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          3.06
_diffrn_reflns_theta_max          25.02
_reflns_number_total              3537
_reflns_number_gt                 3048
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection
' DENZO (Otwinowski and Minor, 1997)'
_computing_cell_refinement        
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction         
' DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997a)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997b)' 
_computing_molecular_graphics     'PLATON (Spek, 1990)'
_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)+(0.0396P)²+0.0996P] 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      SHELXL
_refine_ls_extinction_coef        0.0093(13)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    -0.05(9)
_refine_ls_number_reflns          3537
_refine_ls_number_parameters      348
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0497
_refine_ls_R_factor_gt            0.0375
_refine_ls_wR_factor_ref          0.0832
_refine_ls_wR_factor_gt           0.0783
_refine_ls_goodness_of_fit_ref    1.022
_refine_ls_restrained_S_all       1.022
_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 0.47711(5) 0.89027(5) 0.94122(3) 0.02300(17) Uani 1 1 d . . .
O2 O 0.00049(14) 0.57494(13) 0.82512(7) 0.0260(4) Uani 1 1 d . . .
O1 O 0.03041(15) 0.77516(14) 0.87337(7) 0.0278(4) Uani 1 1 d . . .
N1 N 0.19023(16) 0.61363(18) 0.88112(9) 0.0228(4) Uani 1 1 d . . .
C5 C 0.3669(2) 0.7882(2) 0.88756(11) 0.0221(5) Uani 1 1 d . . .
C12 C 0.4851(2) 1.0892(2) 0.84251(11) 0.0272(5) Uani 1 1 d . . .
C17 C 0.3557(2) 1.0076(2) 0.97586(11) 0.0255(5) Uani 1 1 d . . .
C6 C 0.0694(2) 0.6646(2) 0.86115(11) 0.0224(5) Uani 1 1 d . . .
C1 C 0.2829(2) 0.6864(2) 0.92573(10) 0.0233(5) Uani 1 1 d . . .
C7 C -0.1377(2) 0.6035(2) 0.79884(12) 0.0273(5) Uani 1 1 d . . .
C11 C 0.5567(2) 0.9943(2) 0.87792(10) 0.0234(5) Uani 1 1 d . . .
C16 C 0.6968(2) 0.9797(2) 0.86531(12) 0.0291(6) Uani 1 1 d . . .
C2 C 0.3708(3) 0.5769(2) 0.95434(12) 0.0302(6) Uani 1 1 d . . .
C18 C 0.2176(2) 1.0203(2) 0.95858(12) 0.0291(6) Uani 1 1 d . . .
C15 C 0.7612(3) 1.0552(2) 0.81786(13) 0.0342(6) Uani 1 1 d . . .
C9 C -0.2371(2) 0.6282(3) 0.85533(13) 0.0322(6) Uani 1 1 d . . .
C13 C 0.5506(3) 1.1651(3) 0.79571(12) 0.0353(6) Uani 1 1 d . . .
C3 C 0.3795(2) 0.4773(2) 0.89805(13) 0.0301(6) Uani 1 1 d . . .
C4 C 0.2375(2) 0.4801(2) 0.86749(12) 0.0244(5) Uani 1 1 d . . .
C10 C -0.1735(3) 0.4770(2) 0.76421(16) 0.0356(6) Uani 1 1 d . . .
C22 C 0.4090(3) 1.0928(2) 1.02300(12) 0.0331(6) Uani 1 1 d . . .
C8 C -0.1303(3) 0.7155(3) 0.75074(15) 0.0331(6) Uani 1 1 d . . .
C19 C 0.1379(3) 1.1165(2) 0.98729(14) 0.0393(7) Uani 1 1 d . . .
C20 C 0.1933(3) 1.2014(2) 1.03316(14) 0.0444(7) Uani 1 1 d . . .
C14 C 0.6892(3) 1.1468(2) 0.78332(12) 0.0341(6) Uani 1 1 d . . .
C21 C 0.3291(3) 1.1890(3) 1.05123(14) 0.0424(7) Uani 1 1 d . . .
H5B H 0.305(2) 0.844(2) 0.8617(11) 0.027(6) Uiso 1 1 d . . .
H16 H 0.740(2) 0.917(2) 0.8902(11) 0.034(7) Uiso 1 1 d . . .
H8B H -0.217(3) 0.723(2) 0.7293(12) 0.039(7) Uiso 1 1 d . . .
H1 H 0.224(2) 0.731(2) 0.9591(11) 0.030(6) Uiso 1 1 d . . .
H5A H 0.434(2) 0.742(2) 0.8591(12) 0.029(6) Uiso 1 1 d . . .
H2B H 0.458(3) 0.607(2) 0.9703(12) 0.039(6) Uiso 1 1 d . . .
H10A H -0.165(2) 0.404(2) 0.7949(12) 0.033(7) Uiso 1 1 d . . .
H3B H 0.452(3) 0.508(3) 0.8654(13) 0.046(8) Uiso 1 1 d . . .
H4A H 0.1759(19) 0.4188(19) 0.8915(9) 0.011(5) Uiso 1 1 d . . .
H9C H -0.332(3) 0.650(3) 0.8360(14) 0.050(8) Uiso 1 1 d . . .
H12 H 0.386(3) 1.099(3) 0.8522(13) 0.044(7) Uiso 1 1 d . . .
H22 H 0.502(3) 1.081(2) 1.0349(11) 0.029(6) Uiso 1 1 d . . .
H14 H 0.729(3) 1.200(2) 0.7500(12) 0.035(7) Uiso 1 1 d . . .
H8C H -0.107(2) 0.798(3) 0.7724(13) 0.036(7) Uiso 1 1 d . . .
H18 H 0.176(2) 0.965(2) 0.9283(12) 0.032(7) Uiso 1 1 d . . .
H15 H 0.857(3) 1.039(2) 0.8104(11) 0.026(6) Uiso 1 1 d . . .
H2A H 0.326(3) 0.536(2) 0.9904(13) 0.043(7) Uiso 1 1 d . . .
H8A H -0.063(3) 0.701(2) 0.7163(13) 0.039(7) Uiso 1 1 d . . .
H3A H 0.403(2) 0.385(2) 0.9128(11) 0.026(6) Uiso 1 1 d . . .
H10B H -0.109(3) 0.459(3) 0.7256(15) 0.052(8) Uiso 1 1 d . . .
H9B H -0.249(3) 0.549(3) 0.8807(13) 0.049(8) Uiso 1 1 d . . .
H10C H -0.268(3) 0.484(2) 0.7473(11) 0.036(6) Uiso 1 1 d . . .
H19 H 0.050(3) 1.125(2) 0.9748(11) 0.029(6) Uiso 1 1 d . . .
H20 H 0.133(3) 1.265(3) 1.0526(14) 0.050(8) Uiso 1 1 d . . .
H13 H 0.506(3) 1.232(2) 0.7757(12) 0.042(8) Uiso 1 1 d . . .
H9A H -0.208(2) 0.706(3) 0.8828(12) 0.040(7) Uiso 1 1 d . . .
H21 H 0.366(3) 1.252(3) 1.0866(16) 0.071(10) Uiso 1 1 d . . .
H4B H 0.241(2) 0.464(2) 0.8190(11) 0.026(6) 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
P1 C17 1.826(2) . ?
P1 C11 1.840(2) . ?
P1 C5 1.851(2) . ?
O2 C6 1.352(2) . ?
O2 C7 1.475(2) . ?
O1 C6 1.221(2) . ?
N1 C6 1.348(3) . ?
N1 C4 1.470(3) . ?
N1 C1 1.479(3) . ?
C5 C1 1.536(3) . ?
C5 H5B 0.98(2) . ?
C5 H5A 0.99(2) . ?
C12 C13 1.382(3) . ?
C12 C11 1.396(3) . ?
C12 H12 0.99(3) . ?
C17 C18 1.395(3) . ?
C17 C22 1.394(3) . ?
C1 C2 1.526(3) . ?
C1 H1 1.00(2) . ?
C7 C8 1.508(3) . ?
C7 C10 1.515(3) . ?
C7 C9 1.520(3) . ?
C11 C16 1.394(3) . ?
C16 C15 1.384(3) . ?
C16 H16 0.92(2) . ?
C2 C3 1.534(3) . ?
C2 H2B 0.96(3) . ?
C2 H2A 0.95(3) . ?
C18 C19 1.382(3) . ?
C18 H18 0.93(2) . ?
C15 C14 1.365(4) . ?
C15 H15 0.96(2) . ?
C9 H9C 1.02(3) . ?
C9 H9B 0.97(3) . ?
C9 H9A 1.02(3) . ?
C13 C14 1.385(4) . ?
C13 H13 0.91(3) . ?
C3 C4 1.514(3) . ?
C3 H3B 1.02(3) . ?
C3 H3A 1.01(2) . ?
C4 H4A 1.00(2) . ?
C4 H4B 1.00(2) . ?
C10 H10A 0.98(3) . ?
C10 H10B 1.02(3) . ?
C10 H10C 0.98(3) . ?
C22 C21 1.380(4) . ?
C22 H22 0.95(2) . ?
C8 H8B 0.95(3) . ?
C8 H8C 0.98(3) . ?
C8 H8A 0.97(3) . ?
C19 C20 1.383(4) . ?
C19 H19 0.90(2) . ?
C20 C21 1.377(4) . ?
C20 H20 0.96(3) . ?
C14 H14 0.95(3) . ?
C21 H21 1.03(3) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C17 P1 C11 99.12(10) . . ?
C17 P1 C5 102.94(11) . . ?
C11 P1 C5 99.30(10) . . ?
C6 O2 C7 120.79(16) . . ?
C6 N1 C4 125.23(18) . . ?
C6 N1 C1 121.28(18) . . ?
C4 N1 C1 113.22(17) . . ?
C1 C5 P1 113.37(15) . . ?
C1 C5 H5B 109.7(13) . . ?
P1 C5 H5B 109.9(12) . . ?
C1 C5 H5A 108.6(13) . . ?
P1 C5 H5A 103.3(13) . . ?
H5B C5 H5A 111.9(18) . . ?
C13 C12 C11 121.0(2) . . ?
C13 C12 H12 122.0(16) . . ?
C11 C12 H12 117.0(16) . . ?
C18 C17 C22 118.2(2) . . ?
C18 C17 P1 126.00(18) . . ?
C22 C17 P1 115.80(18) . . ?
O1 C6 N1 124.8(2) . . ?
O1 C6 O2 125.9(2) . . ?
N1 C6 O2 109.32(18) . . ?
N1 C1 C2 101.72(17) . . ?
N1 C1 C5 111.07(17) . . ?
C2 C1 C5 113.15(19) . . ?
N1 C1 H1 107.1(13) . . ?
C2 C1 H1 113.6(12) . . ?
C5 C1 H1 109.7(13) . . ?
O2 C7 C8 109.96(18) . . ?
O2 C7 C10 101.96(17) . . ?
C8 C7 C10 111.3(2) . . ?
O2 C7 C9 109.91(18) . . ?
C8 C7 C9 113.0(2) . . ?
C10 C7 C9 110.2(2) . . ?
C16 C11 C12 118.0(2) . . ?
C16 C11 P1 118.49(18) . . ?
C12 C11 P1 123.54(16) . . ?
C15 C16 C11 120.6(2) . . ?
C15 C16 H16 124.7(15) . . ?
C11 C16 H16 114.7(15) . . ?
C1 C2 C3 103.76(19) . . ?
C1 C2 H2B 112.7(14) . . ?
C3 C2 H2B 114.7(14) . . ?
C1 C2 H2A 110.9(16) . . ?
C3 C2 H2A 107.8(15) . . ?
H2B C2 H2A 107(2) . . ?
C19 C18 C17 120.0(2) . . ?
C19 C18 H18 117.9(15) . . ?
C17 C18 H18 122.1(14) . . ?
C14 C15 C16 120.6(3) . . ?
C14 C15 H15 122.6(14) . . ?
C16 C15 H15 116.8(14) . . ?
C7 C9 H9C 108.7(16) . . ?
C7 C9 H9B 109.5(16) . . ?
H9C C9 H9B 107(2) . . ?
C7 C9 H9A 111.5(14) . . ?
H9C C9 H9A 106(2) . . ?
H9B C9 H9A 113.8(19) . . ?
C12 C13 C14 119.8(3) . . ?
C12 C13 H13 121.0(16) . . ?
C14 C13 H13 118.9(17) . . ?
C4 C3 C2 103.97(19) . . ?
C4 C3 H3B 111.0(15) . . ?
C2 C3 H3B 108.4(14) . . ?
C4 C3 H3A 110.1(12) . . ?
C2 C3 H3A 114.3(12) . . ?
H3B C3 H3A 109.0(19) . . ?
N1 C4 C3 103.06(17) . . ?
N1 C4 H4A 107.9(11) . . ?
C3 C4 H4A 109.7(10) . . ?
N1 C4 H4B 110.7(12) . . ?
C3 C4 H4B 111.5(13) . . ?
H4A C4 H4B 113.4(17) . . ?
C7 C10 H10A 109.9(14) . . ?
C7 C10 H10B 111.6(16) . . ?
H10A C10 H10B 107(2) . . ?
C7 C10 H10C 108.2(14) . . ?
H10A C10 H10C 111.3(19) . . ?
H10B C10 H10C 109(2) . . ?
C21 C22 C17 121.4(3) . . ?
C21 C22 H22 121.7(14) . . ?
C17 C22 H22 116.9(14) . . ?
C7 C8 H8B 108.3(15) . . ?
C7 C8 H8C 112.3(15) . . ?
H8B C8 H8C 110(2) . . ?
C7 C8 H8A 112.5(15) . . ?
H8B C8 H8A 106(2) . . ?
H8C C8 H8A 107(2) . . ?
C18 C19 C20 120.9(3) . . ?
C18 C19 H19 119.3(15) . . ?
C20 C19 H19 119.8(15) . . ?
C21 C20 C19 119.6(3) . . ?
C21 C20 H20 122.4(16) . . ?
C19 C20 H20 117.9(16) . . ?
C15 C14 C13 120.0(2) . . ?
C15 C14 H14 123.4(15) . . ?
C13 C14 H14 116.6(15) . . ?
C20 C21 C22 119.8(3) . . ?
C20 C21 H21 117.6(18) . . ?
C22 C21 H21 122.7(18) . . ?
 
_diffrn_measured_fraction_theta_max    0.993
_diffrn_reflns_theta_full              25.02
_diffrn_measured_fraction_theta_full   0.993
_refine_diff_density_max    0.235
_refine_diff_density_min   -0.192
_refine_diff_density_rms    0.039
