data_pa75
_audit_creation_date               2018-10-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/1'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C17 H22 N3 O3 P'
_chemical_formula_sum              'C17 H22 N3 O3 P'
_chemical_formula_weight           347.34
_chemical_melting_point            ?
_chemical_oxdiff_formula           'C17 H22 N3 O3 P'
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'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'triclinic'
_space_group_IT_number             2
_space_group_name_H-M_alt          'P -1'
_space_group_name_Hall             '-P 1'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'

_cell_length_a                     8.2122(7)
_cell_length_b                     9.2282(7)
_cell_length_c                     12.0429(9)
_cell_angle_alpha                  87.574(6)
_cell_angle_beta                   87.187(6)
_cell_angle_gamma                  71.195(7)
_cell_volume                       862.56(12)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      2666
_cell_measurement_temperature      293(2)
_cell_measurement_theta_max        30.6050
_cell_measurement_theta_min        3.0830
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.180
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.90448
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              ''
_exptl_crystal_density_diffrn      1.337
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         ''
_exptl_crystal_F_000               368
_exptl_crystal_size_max            ?
_exptl_crystal_size_mid            ?
_exptl_crystal_size_min            ?
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0256
_diffrn_reflns_av_unetI/netI       0.0458
_diffrn_reflns_Laue_measured_fraction_full  0.999
_diffrn_reflns_Laue_measured_fraction_max  0.999
_diffrn_reflns_limit_h_max         10
_diffrn_reflns_limit_h_min         -8
_diffrn_reflns_limit_k_max         11
_diffrn_reflns_limit_k_min         -8
_diffrn_reflns_limit_l_max         14
_diffrn_reflns_limit_l_min         -15
_diffrn_reflns_number              6987
_diffrn_reflns_point_group_measured_fraction_full  0.999
_diffrn_reflns_point_group_measured_fraction_max  0.999
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           27.499
_diffrn_reflns_theta_min           2.844
_diffrn_ambient_temperature        293(2)
_diffrn_detector_area_resol_mean   16.2096
_diffrn_measured_fraction_theta_full  0.999
_diffrn_measured_fraction_theta_max  0.999
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -44.00   36.00   1.0000    9.0700
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -57.0000   90.0000 80

#__ type_ start__ end____ width___ exp.time_
  2 omega   22.00   65.00   1.0000    9.0700
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000 -120.0000 43

#__ type_ start__ end____ width___ exp.time_
  3 omega   46.00   91.00   1.0000    9.0700
omega____ theta____ kappa____ phi______ frames
    -       23.3616 -178.0000  120.0000 45

#__ type_ start__ end____ width___ exp.time_
  4 omega  -21.00   65.00   1.0000    9.0700
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000  -30.0000 86

#__ type_ start__ end____ width___ exp.time_
  5 omega   33.00   65.00   1.0000    9.0700
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000  120.0000 32

#__ type_ start__ end____ width___ exp.time_
  6 omega  -20.00   96.00   1.0000    9.0700
omega____ theta____ kappa____ phi______ frames
    -       23.3616   19.0000  -90.0000 116
;
_diffrn_measurement_device_type    'Xcalibur, Eos'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_UB_11        0.0168366000
_diffrn_orient_matrix_UB_12        0.0121139000
_diffrn_orient_matrix_UB_13        -0.0573760000
_diffrn_orient_matrix_UB_21        -0.0516610000
_diffrn_orient_matrix_UB_22        0.0778878000
_diffrn_orient_matrix_UB_23        0.0038874000
_diffrn_orient_matrix_UB_31        0.0733794000
_diffrn_orient_matrix_UB_32        0.0196158000
_diffrn_orient_matrix_UB_33        0.0131508000
_diffrn_radiation_monochromator    graphite
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  3363
_reflns_number_total               3959
_reflns_odcompleteness_completeness  99.89
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       28.51
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.349
_refine_diff_density_min           -0.494
_refine_diff_density_rms           0.054
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.051
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       221
_refine_ls_number_reflns           3959
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0479
_refine_ls_R_factor_gt             0.0388
_refine_ls_restrained_S_all        1.051
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0373P)²+0.3041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0909
_refine_ls_wR_factor_ref           0.0983
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00D(H00D), C00L(H00L)
2.b Secondary CH2 refined with riding coordinates:
 C00C(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00E(H00E), C00F(H00F), C00H(H00H), C00I(H00I), C00J(H00J)
2.d Idealised Me refined as rotating group:
 C00K(H00C,H00G,H00K), C00M(H00M,H00N,H00O), C00N(H00P,H00Q,H00R), C00O(H00S,
 H00T,H00U)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
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_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 P001 P 0.18217(5) 0.68758(5) 0.20282(3) 0.01374(11) Uani 1 1 d . . . . .
 O002 O 0.08911(13) 0.59187(13) 0.14048(9) 0.0173(2) Uani 1 1 d . . . . .
 O003 O 0.32124(12) 0.70410(12) 0.11314(9) 0.0151(2) Uani 1 1 d . . . . .
 O004 O 0.06758(13) 0.83043(13) 0.24996(9) 0.0191(2) Uani 1 1 d . . . . .
 N005 N 0.37739(15) 0.71403(15) 0.45084(10) 0.0141(3) Uani 1 1 d . . . . .
 N006 N 0.66093(16) 0.63021(16) 0.43284(11) 0.0191(3) Uani 1 1 d . . . . .
 N007 N 0.59399(16) 0.55746(16) 0.35723(11) 0.0191(3) Uani 1 1 d . . . . .
 C008 C 0.42606(19) 0.60883(18) 0.36852(12) 0.0155(3) Uani 1 1 d . . . . .
 C009 C 0.67404(19) 0.85090(18) 0.60987(13) 0.0176(3) Uani 1 1 d . . . . .
 H009 H 0.781020 0.795066 0.579350 0.021 Uiso 1 1 calc R . . . .
 C00A C 0.52435(19) 0.82857(18) 0.57381(12) 0.0151(3) Uani 1 1 d . . . . .
 C00B C 0.52933(18) 0.72395(18) 0.48808(12) 0.0152(3) Uani 1 1 d . . . . .
 C00C C 0.30796(19) 0.55515(18) 0.30428(13) 0.0161(3) Uani 1 1 d . . . . .
 H00A H 0.229404 0.526295 0.356606 0.019 Uiso 1 1 calc R . . . .
 H00B H 0.375865 0.463339 0.266327 0.019 Uiso 1 1 calc R . . . .
 C00D C -0.06845(18) 0.56552(18) 0.18835(13) 0.0165(3) Uani 1 1 d . . . . .
 H00D H -0.102295 0.618791 0.258687 0.020 Uiso 1 1 calc R . . . .
 C00E C 0.5015(2) 1.04053(19) 0.73582(13) 0.0194(3) Uani 1 1 d . . . . .
 H00E H 0.494387 1.111698 0.789786 0.023 Uiso 1 1 calc R . . . .
 C00F C 0.3537(2) 1.01946(18) 0.70104(13) 0.0181(3) Uani 1 1 d . . . . .
 H00F H 0.247396 1.076420 0.731860 0.022 Uiso 1 1 calc R . . . .
 C00G C 0.36192(19) 0.91296(18) 0.61961(13) 0.0154(3) Uani 1 1 d . . . . .
 C00H C 0.21658(19) 0.79504(18) 0.49754(13) 0.0171(3) Uani 1 1 d . . . . .
 H00H H 0.116777 0.782889 0.472106 0.021 Uiso 1 1 calc R . . . .
 C00I C 0.20875(19) 0.89053(18) 0.57961(13) 0.0177(3) Uani 1 1 d . . . . .
 H00I H 0.102082 0.943893 0.611799 0.021 Uiso 1 1 calc R . . . .
 C00J C 0.6626(2) 0.95525(19) 0.69029(13) 0.0193(3) Uani 1 1 d . . . . .
 H00J H 0.762044 0.969378 0.714603 0.023 Uiso 1 1 calc R . . . .
 C00K C -0.20765(19) 0.63038(19) 0.10597(14) 0.0189(3) Uani 1 1 d . . . . .
 H00C H -0.220273 0.736203 0.090150 0.028 Uiso 1 1 calc GR . . . .
 H00G H -0.314395 0.621905 0.136728 0.028 Uiso 1 1 calc GR . . . .
 H00K H -0.177006 0.574374 0.038538 0.028 Uiso 1 1 calc GR . . . .
 C00L C 0.2677(2) 0.78245(18) 0.00521(13) 0.0170(3) Uani 1 1 d . . . . .
 H00L H 0.160789 0.766214 -0.014793 0.020 Uiso 1 1 calc R . . . .
 C00M C -0.0274(2) 0.39567(19) 0.20939(15) 0.0229(4) Uani 1 1 d . . . . .
 H00M H 0.005083 0.343825 0.140317 0.034 Uiso 1 1 calc GR . . . .
 H00N H -0.126938 0.375100 0.242050 0.034 Uiso 1 1 calc GR . . . .
 H00O H 0.065956 0.359823 0.259213 0.034 Uiso 1 1 calc GR . . . .
 C00N C 0.4079(2) 0.7071(2) -0.07877(14) 0.0239(4) Uani 1 1 d . . . . .
 H00P H 0.513333 0.721967 -0.059525 0.036 Uiso 1 1 calc GR . . . .
 H00Q H 0.376388 0.751728 -0.151252 0.036 Uiso 1 1 calc GR . . . .
 H00R H 0.423397 0.599454 -0.079145 0.036 Uiso 1 1 calc GR . . . .
 C00O C 0.2361(2) 0.9520(2) 0.01373(15) 0.0262(4) Uani 1 1 d . . . . .
 H00S H 0.153028 0.991563 0.072972 0.039 Uiso 1 1 calc GR . . . .
 H00T H 0.193247 1.003103 -0.055087 0.039 Uiso 1 1 calc GR . . . .
 H00U H 0.342020 0.969328 0.028729 0.039 Uiso 1 1 calc GR . . . .


_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
 P001 O002 1.5733(11) . ?
 P001 O003 1.5720(11) . ?
 P001 O004 1.4686(11) . ?
 P001 C00C 1.7991(16) . ?
 O002 C00D 1.4776(17) . ?
 O003 C00L 1.4755(18) . ?
 N005 C008 1.370(2) . ?
 N005 C00B 1.3779(18) . ?
 N005 C00H 1.3948(19) . ?
 N006 N007 1.3859(18) . ?
 N006 C00B 1.317(2) . ?
 N007 C008 1.3080(19) . ?
 C008 C00C 1.483(2) . ?
 C009 H009 0.9300 . ?
 C009 C00A 1.402(2) . ?
 C009 C00J 1.373(2) . ?
 C00A C00B 1.433(2) . ?
 C00A C00G 1.409(2) . ?
 C00C H00A 0.9700 . ?
 C00C H00B 0.9700 . ?
 C00D H00D 0.9800 . ?
 C00D C00K 1.506(2) . ?
 C00D C00M 1.506(2) . ?
 C00E H00E 0.9300 . ?
 C00E C00F 1.377(2) . ?
 C00E C00J 1.402(2) . ?
 C00F H00F 0.9300 . ?
 C00F C00G 1.402(2) . ?
 C00G C00I 1.447(2) . ?
 C00H H00H 0.9300 . ?
 C00H C00I 1.337(2) . ?
 C00I H00I 0.9300 . ?
 C00J H00J 0.9300 . ?
 C00K H00C 0.9600 . ?
 C00K H00G 0.9600 . ?
 C00K H00K 0.9600 . ?
 C00L H00L 0.9800 . ?
 C00L C00N 1.503(2) . ?
 C00L C00O 1.509(2) . ?
 C00M H00M 0.9600 . ?
 C00M H00N 0.9600 . ?
 C00M H00O 0.9600 . ?
 C00N H00P 0.9600 . ?
 C00N H00Q 0.9600 . ?
 C00N H00R 0.9600 . ?
 C00O H00S 0.9600 . ?
 C00O H00T 0.9600 . ?
 C00O H00U 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
 O002 P001 C00C 104.55(7) . . ?
 O003 P001 O002 102.26(6) . . ?
 O003 P001 C00C 103.24(6) . . ?
 O004 P001 O002 115.04(6) . . ?
 O004 P001 O003 116.29(6) . . ?
 O004 P001 C00C 113.86(7) . . ?
 C00D O002 P001 121.40(9) . . ?
 C00L O003 P001 120.17(9) . . ?
 C008 N005 C00B 104.97(12) . . ?
 C008 N005 C00H 132.08(13) . . ?
 C00B N005 C00H 122.89(13) . . ?
 C00B N006 N007 107.00(12) . . ?
 C008 N007 N006 108.20(13) . . ?
 N005 C008 C00C 125.65(13) . . ?
 N007 C008 N005 109.88(14) . . ?
 N007 C008 C00C 124.43(14) . . ?
 C00A C009 H009 120.0 . . ?
 C00J C009 H009 120.0 . . ?
 C00J C009 C00A 119.96(14) . . ?
 C009 C00A C00B 122.00(14) . . ?
 C009 C00A C00G 120.28(15) . . ?
 C00G C00A C00B 117.69(13) . . ?
 N005 C00B C00A 119.49(13) . . ?
 N006 C00B N005 109.94(13) . . ?
 N006 C00B C00A 130.56(14) . . ?
 P001 C00C H00A 108.1 . . ?
 P001 C00C H00B 108.1 . . ?
 C008 C00C P001 116.91(11) . . ?
 C008 C00C H00A 108.1 . . ?
 C008 C00C H00B 108.1 . . ?
 H00A C00C H00B 107.3 . . ?
 O002 C00D H00D 109.6 . . ?
 O002 C00D C00K 107.17(12) . . ?
 O002 C00D C00M 107.54(12) . . ?
 C00K C00D H00D 109.6 . . ?
 C00M C00D H00D 109.6 . . ?
 C00M C00D C00K 113.12(13) . . ?
 C00F C00E H00E 119.8 . . ?
 C00F C00E C00J 120.33(15) . . ?
 C00J C00E H00E 119.8 . . ?
 C00E C00F H00F 119.7 . . ?
 C00E C00F C00G 120.61(14) . . ?
 C00G C00F H00F 119.7 . . ?
 C00A C00G C00I 119.42(14) . . ?
 C00F C00G C00A 118.64(14) . . ?
 C00F C00G C00I 121.93(14) . . ?
 N005 C00H H00H 120.7 . . ?
 C00I C00H N005 118.68(14) . . ?
 C00I C00H H00H 120.7 . . ?
 C00G C00I H00I 119.1 . . ?
 C00H C00I C00G 121.71(14) . . ?
 C00H C00I H00I 119.1 . . ?
 C009 C00J C00E 120.18(15) . . ?
 C009 C00J H00J 119.9 . . ?
 C00E C00J H00J 119.9 . . ?
 C00D C00K H00C 109.5 . . ?
 C00D C00K H00G 109.5 . . ?
 C00D C00K H00K 109.5 . . ?
 H00C C00K H00G 109.5 . . ?
 H00C C00K H00K 109.5 . . ?
 H00G C00K H00K 109.5 . . ?
 O003 C00L H00L 108.9 . . ?
 O003 C00L C00N 106.45(12) . . ?
 O003 C00L C00O 110.00(13) . . ?
 C00N C00L H00L 108.9 . . ?
 C00N C00L C00O 113.47(14) . . ?
 C00O C00L H00L 108.9 . . ?
 C00D C00M H00M 109.5 . . ?
 C00D C00M H00N 109.5 . . ?
 C00D C00M H00O 109.5 . . ?
 H00M C00M H00N 109.5 . . ?
 H00M C00M H00O 109.5 . . ?
 H00N C00M H00O 109.5 . . ?
 C00L C00N H00P 109.5 . . ?
 C00L C00N H00Q 109.5 . . ?
 C00L C00N H00R 109.5 . . ?
 H00P C00N H00Q 109.5 . . ?
 H00P C00N H00R 109.5 . . ?
 H00Q C00N H00R 109.5 . . ?
 C00L C00O H00S 109.5 . . ?
 C00L C00O H00T 109.5 . . ?
 C00L C00O H00U 109.5 . . ?
 H00S C00O H00T 109.5 . . ?
 H00S C00O H00U 109.5 . . ?
 H00T C00O H00U 109.5 . . ?

_smtbx_masks_special_details       ?
loop_
  _smtbx_masks_void_nr
  _smtbx_masks_void_average_x
  _smtbx_masks_void_average_y
  _smtbx_masks_void_average_z
  _smtbx_masks_void_volume
  _smtbx_masks_void_count_electrons
  _smtbx_masks_void_content
 1 0.000 0.500 0.500 20.8 9.7 ?

_olex2_submission_special_instructions  'No special instructions were received'
