data_8930-10650_ka69
_audit_creation_date               2018-10-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2014/7'
_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.

Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst., 40, 786-790;
Palatinus, L. & van der Lee, A. (2008). J. Appl. Cryst. 41, 975-984;
Palatinus, L., Prathapa, S. J. & van Smaalen, S. (2012). J. Appl. Cryst. 45,
 575-580.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C13 H19 Cl N3 O3 P'
_chemical_formula_sum              'C13 H19 Cl N3 O3 P'
_chemical_formula_weight           331.73
_chemical_absolute_configuration   ?
_chemical_melting_point            ?
_chemical_oxdiff_formula           'C11 H15 Cl 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'
 'Cl' 'Cl' 0.1484 0.1585 '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        'orthorhombic'
_space_group_IT_number             33
_space_group_name_H-M_alt          'P n a 21'
_space_group_name_Hall             'P 2c -2n'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, z+1/2'
 '-x+1/2, y+1/2, z+1/2'
 'x+1/2, -y+1/2, z'

_cell_length_a                     24.9968(19)
_cell_length_b                     5.3041(2)
_cell_length_c                     12.0306(5)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       1595.08(15)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      2946
_cell_measurement_temperature      100(2)
_cell_measurement_theta_max        29.6250
_cell_measurement_theta_min        3.3880
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.352
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.62552
_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              'clear colourless'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     .
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.381
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         plate
_exptl_crystal_F_000               696
_exptl_crystal_size_max            0.6
_exptl_crystal_size_mid            0.6
_exptl_crystal_size_min            0.15
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0334
_diffrn_reflns_av_unetI/netI       0.0436
_diffrn_reflns_Laue_measured_fraction_full  0.999
_diffrn_reflns_Laue_measured_fraction_max  0.999
_diffrn_reflns_limit_h_max         27
_diffrn_reflns_limit_h_min         -32
_diffrn_reflns_limit_k_max         6
_diffrn_reflns_limit_k_min         -6
_diffrn_reflns_limit_l_max         15
_diffrn_reflns_limit_l_min         -15
_diffrn_reflns_number              9804
_diffrn_reflns_point_group_measured_fraction_full  0.998
_diffrn_reflns_point_group_measured_fraction_max  0.997
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           27.489
_diffrn_reflns_theta_min           3.260
_diffrn_ambient_temperature        100(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  -95.00    3.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -38.0000 -180.0000 98

#__ type_ start__ end____ width___ exp.time_
  2 omega   46.00   84.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616 -130.0000 -123.0000 38

#__ type_ start__ end____ width___ exp.time_
  3 omega  -16.00   28.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -77.0000   60.0000 44

#__ type_ start__ end____ width___ exp.time_
  4 omega  -96.00  -69.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241 -178.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega  -60.00  -35.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241 -178.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega  -18.00    8.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -77.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega  -88.00   -6.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -38.0000   90.0000 82
;
_diffrn_measurement_device_type    'Xcalibur, Eos'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_UB_11        -0.0283488000
_diffrn_orient_matrix_UB_12        0.0038407000
_diffrn_orient_matrix_UB_13        0.0021742000
_diffrn_orient_matrix_UB_21        -0.0010207000
_diffrn_orient_matrix_UB_22        0.0049444000
_diffrn_orient_matrix_UB_23        -0.0588773000
_diffrn_orient_matrix_UB_31        -0.0008586000
_diffrn_orient_matrix_UB_32        -0.1335636000
_diffrn_orient_matrix_UB_33        -0.0021435000
_diffrn_radiation_monochromator    graphite
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage           0.906
_reflns_Friedel_fraction_full      0.996
_reflns_Friedel_fraction_max       0.995
_reflns_number_gt                  3298
_reflns_number_total               3644
_reflns_odcompleteness_completeness  99.71
_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.
 
 _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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max           0.322
_refine_diff_density_min           -0.253
_refine_diff_density_rms           0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1359 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.04(4)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.065
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       194
_refine_ls_number_reflns           3644
_refine_ls_number_restraints       1
_refine_ls_R_factor_all            0.0431
_refine_ls_R_factor_gt             0.0363
_refine_ls_restrained_S_all        1.065
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0349P)²+0.1494P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0738
_refine_ls_wR_factor_ref           0.0765
_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:
 C8(H8), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C10(H10)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C6(H6A,H6B,H6C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       iterative
_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
 Cl1 Cl 0.60302(4) -0.08595(15) 0.69642(7) 0.0273(2) Uani 1 1 d . . . . .
 P2 P 0.62422(3) 0.69286(13) 0.31728(7) 0.01385(17) Uani 1 1 d . . . . .
 O1 O 0.61257(8) 0.6654(4) 0.18856(18) 0.0157(4) Uani 1 1 d . . . . .
 O2 O 0.62639(10) 0.9554(4) 0.35596(18) 0.0215(5) Uani 1 1 d . . . . .
 C3 C 0.68457(12) 0.5151(6) 0.3440(2) 0.0157(6) Uani 1 1 d . . . . .
 H3A H 0.6770 0.3365 0.3365 0.019 Uiso 1 1 calc R . . . .
 H3B H 0.7115 0.5596 0.2892 0.019 Uiso 1 1 calc R . . . .
 N4 N 0.74098(11) 0.7397(5) 0.4846(2) 0.0203(6) Uani 1 1 d . . . . .
 C5 C 0.71780(13) 0.5529(6) 0.6378(3) 0.0171(7) Uani 1 1 d . . . . .
 N6 N 0.68922(10) 0.4411(4) 0.5521(2) 0.0137(5) Uani 1 1 d . . . . .
 C7 C 0.70594(12) 0.5661(6) 0.4579(2) 0.0155(6) Uani 1 1 d . . . . .
 N8 N 0.74909(11) 0.7332(5) 0.5985(2) 0.0196(6) Uani 1 1 d . . . . .
 C9 C 0.64677(13) 0.1629(5) 0.6730(3) 0.0178(7) Uani 1 1 d . . . . .
 O10 O 0.58072(9) 0.5218(4) 0.37359(17) 0.0172(5) Uani 1 1 d . . . . .
 C1 C 0.59616(15) 1.0518(6) 0.0877(3) 0.0264(8) Uani 1 1 d . . . . .
 H1A H 0.5667 0.9765 0.0486 0.040 Uiso 1 1 calc GR . . . .
 H1B H 0.6120 1.1805 0.0422 0.040 Uiso 1 1 calc GR . . . .
 H1C H 0.5835 1.1252 0.1557 0.040 Uiso 1 1 calc GR . . . .
 C2 C 0.65332(12) 0.2449(5) 0.5677(3) 0.0149(6) Uani 1 1 d . . . . .
 H2 H 0.6347 0.1734 0.5086 0.018 Uiso 1 1 calc R . . . .
 C4 C 0.67533(14) 0.2681(6) 0.7644(3) 0.0202(7) Uani 1 1 d . . . . .
 H4 H 0.6700 0.2052 0.8357 0.024 Uiso 1 1 calc R . . . .
 C6 C 0.48940(19) 0.6112(13) 0.3228(4) 0.081(2) Uani 1 1 d . . . . .
 H6A H 0.4997 0.7265 0.2651 0.122 Uiso 1 1 calc GR . . . .
 H6B H 0.4550 0.6584 0.3513 0.122 Uiso 1 1 calc GR . . . .
 H6C H 0.4876 0.4435 0.2930 0.122 Uiso 1 1 calc GR . . . .
 C8 C 0.63734(13) 0.8529(6) 0.1135(3) 0.0176(7) Uani 1 1 d . . . . .
 H8 H 0.6678 0.9317 0.1514 0.021 Uiso 1 1 calc R . . . .
 C10 C 0.71045(13) 0.4601(6) 0.7476(3) 0.0196(7) Uani 1 1 d . . . . .
 H10 H 0.7293 0.5295 0.8068 0.024 Uiso 1 1 calc R . . . .
 C11 C 0.52958(14) 0.6192(6) 0.4141(3) 0.0229(8) Uani 1 1 d . . . . .
 H11 H 0.5342 0.7938 0.4389 0.027 Uiso 1 1 calc R . . . .
 C12 C 0.51395(16) 0.4587(8) 0.5107(3) 0.0412(10) Uani 1 1 d . . . . .
 H12A H 0.5089 0.2881 0.4863 0.062 Uiso 1 1 calc GR . . . .
 H12B H 0.4812 0.5210 0.5422 0.062 Uiso 1 1 calc GR . . . .
 H12C H 0.5417 0.4638 0.5659 0.062 Uiso 1 1 calc GR . . . .
 C13 C 0.65739(16) 0.7106(6) 0.0129(3) 0.0263(8) Uani 1 1 d . . . . .
 H13A H 0.6810 0.5780 0.0364 0.039 Uiso 1 1 calc GR . . . .
 H13B H 0.6764 0.8240 -0.0352 0.039 Uiso 1 1 calc GR . . . .
 H13C H 0.6276 0.6394 -0.0264 0.039 Uiso 1 1 calc GR . . . .

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
 Cl1 0.0370(5) 0.0210(4) 0.0238(4) 0.0081(4) 0.0043(4) -0.0050(4)
 P2 0.0231(4) 0.0101(3) 0.0084(3) -0.0002(3) -0.0011(3) -0.0008(3)
 O1 0.0261(12) 0.0119(10) 0.0090(10) 0.0014(9) -0.0023(9) -0.0043(8)
 O2 0.0370(14) 0.0133(11) 0.0142(10) -0.0004(9) -0.0047(10) -0.0011(10)
 C3 0.0203(16) 0.0167(15) 0.0100(15) -0.0013(12) 0.0005(11) -0.0022(12)
 N4 0.0223(14) 0.0257(15) 0.0128(13) -0.0015(12) -0.0011(11) -0.0038(11)
 C5 0.0185(17) 0.0196(17) 0.0132(15) -0.0033(13) -0.0022(12) 0.0039(13)
 N6 0.0177(13) 0.0149(12) 0.0084(12) -0.0013(10) -0.0007(10) 0.0013(10)
 C7 0.0172(15) 0.0171(15) 0.0122(15) 0.0005(13) -0.0005(12) 0.0003(12)
 N8 0.0228(14) 0.0247(15) 0.0112(13) -0.0010(11) -0.0025(11) -0.0024(11)
 C9 0.0215(16) 0.0132(14) 0.0186(17) 0.0037(12) 0.0009(13) 0.0028(13)
 O10 0.0213(12) 0.0136(11) 0.0166(11) 0.0011(9) 0.0038(9) 0.0019(9)
 C1 0.040(2) 0.0170(17) 0.0227(18) 0.0050(14) -0.0010(15) 0.0009(15)
 C2 0.0195(15) 0.0110(14) 0.0142(15) -0.0016(12) 0.0009(12) 0.0001(12)
 C4 0.0308(19) 0.0206(16) 0.0092(14) 0.0030(13) 0.0016(13) 0.0071(14)
 C6 0.036(3) 0.179(6) 0.028(2) 0.019(4) -0.007(2) 0.025(3)
 C8 0.0256(17) 0.0144(15) 0.0130(15) 0.0054(13) -0.0004(13) -0.0043(13)
 C10 0.0249(18) 0.0238(17) 0.0101(14) -0.0018(14) -0.0016(13) 0.0059(14)
 C11 0.0225(18) 0.0244(18) 0.0218(18) 0.0013(14) 0.0052(14) 0.0061(14)
 C12 0.031(2) 0.054(3) 0.039(2) 0.016(2) 0.0172(19) 0.0107(18)
 C13 0.043(2) 0.0207(17) 0.0156(17) 0.0065(14) 0.0062(15) 0.0016(15)

_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
 Cl1 C9 1.737(3) . ?
 P2 O1 1.582(2) . ?
 P2 O2 1.469(2) . ?
 P2 C3 1.808(3) . ?
 P2 O10 1.570(2) . ?
 O1 C8 1.479(3) . ?
 C3 C7 1.496(4) . ?
 N4 C7 1.311(4) . ?
 N4 N8 1.385(3) . ?
 C5 N6 1.388(4) . ?
 C5 N8 1.323(4) . ?
 C5 C10 1.421(4) . ?
 N6 C7 1.378(4) . ?
 N6 C2 1.387(4) . ?
 C9 C2 1.349(4) . ?
 C9 C4 1.425(4) . ?
 O10 C11 1.462(4) . ?
 C1 C8 1.506(4) . ?
 C4 C10 1.360(5) . ?
 C6 C11 1.489(6) . ?
 C8 C13 1.512(4) . ?
 C11 C12 1.493(5) . ?

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
 O1 P2 C3 106.22(12) . . ?
 O2 P2 O1 113.83(12) . . ?
 O2 P2 C3 114.04(14) . . ?
 O2 P2 O10 115.88(13) . . ?
 O10 P2 O1 103.98(11) . . ?
 O10 P2 C3 101.55(13) . . ?
 C8 O1 P2 117.27(18) . . ?
 C7 C3 P2 111.5(2) . . ?
 C7 N4 N8 108.8(3) . . ?
 N6 C5 C10 118.4(3) . . ?
 N8 C5 N6 110.3(3) . . ?
 N8 C5 C10 131.3(3) . . ?
 C7 N6 C5 104.4(2) . . ?
 C7 N6 C2 132.0(3) . . ?
 C2 N6 C5 123.6(3) . . ?
 N4 C7 C3 126.1(3) . . ?
 N4 C7 N6 109.9(3) . . ?
 N6 C7 C3 123.9(3) . . ?
 C5 N8 N4 106.6(3) . . ?
 C2 C9 Cl1 118.3(3) . . ?
 C2 C9 C4 122.5(3) . . ?
 C4 C9 Cl1 119.2(2) . . ?
 C11 O10 P2 123.0(2) . . ?
 C9 C2 N6 116.6(3) . . ?
 C10 C4 C9 120.1(3) . . ?
 O1 C8 C1 108.1(3) . . ?
 O1 C8 C13 106.9(2) . . ?
 C1 C8 C13 114.2(3) . . ?
 C4 C10 C5 118.8(3) . . ?
 O10 C11 C6 109.5(3) . . ?
 O10 C11 C12 106.7(3) . . ?
 C6 C11 C12 112.4(4) . . ?

_olex2_submission_special_instructions  'No special instructions were received'
