 
data_1_a
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C16 H36 Cl2 N O2 P' 
_chemical_formula_weight          376.33

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'
 'P'  'P'   0.1023   0.0942
 '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'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/n'
_space_group_name_Hall            '-P 2yn'
 
_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.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    10.2286(19)
_cell_length_b                    12.961(2)
_cell_length_c                    16.698(3)
_cell_angle_alpha                 90
_cell_angle_beta                  92.173(3)
_cell_angle_gamma                 90
_cell_volume                      2212.1(7)
_cell_formula_units_Z             4
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     2985
_cell_measurement_theta_min       2.44
_cell_measurement_theta_max       21.34
 
_exptl_crystal_description        block
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.130          
_exptl_crystal_F_000              816
_exptl_transmission_factor_min    0.6402  
_exptl_transmission_factor_max    0.7453
_exptl_crystal_size_max           0.300
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.372
_shelx_estimated_absorpt_T_min    0.897
_shelx_estimated_absorpt_T_max    0.929
_exptl_absorpt_correction_type    Multi-scan
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    SADABS
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       296(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'Bruker APEX II area detector' 
_diffrn_measurement_method        'ω scan'
_diffrn_detector_area_resol_mean  'fine-focus sealed tube'
_diffrn_reflns_number             12259
_diffrn_reflns_av_unetI/netI      0.0307
_diffrn_reflns_av_R_equivalents   0.0260
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          2.376
_diffrn_reflns_theta_max          26.259
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.997
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              4460
_reflns_number_gt                 2535
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_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.
;
 
_computing_data_collection        'Bruker SMART APEX II'
_computing_cell_refinement        'Bruker SMART'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     SHELXTL 
_computing_publication_material   SHELXTL 
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+1.4495P] 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          4460
_refine_ls_number_parameters      203
_refine_ls_number_restraints      29
_refine_ls_R_factor_all           0.1115
_refine_ls_R_factor_gt            0.0738
_refine_ls_wR_factor_ref          0.2322
_refine_ls_wR_factor_gt           0.2048
_refine_ls_goodness_of_fit_ref    1.012
_refine_ls_restrained_S_all       1.176
_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_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
C1 C 0.6332(4) 0.3584(3) 0.5349(2) 0.0788(10) Uani 1 1 d . . . . .
H1A H 0.5408 0.3653 0.5206 0.095 Uiso 1 1 calc R U . . .
H1B H 0.6747 0.4237 0.5229 0.095 Uiso 1 1 calc R U . . .
C2 C 0.6889(5) 0.2777(4) 0.4832(2) 0.0951(13) Uani 1 1 d . . . . .
H2A H 0.6445 0.2126 0.4914 0.114 Uiso 1 1 calc R U . . .
H2B H 0.7811 0.2683 0.4973 0.114 Uiso 1 1 calc R U . . .
C3 C 0.6720(5) 0.3106(4) 0.3951(2) 0.1112(16) Uani 1 1 d . . . . .
H3A H 0.5796 0.3185 0.3811 0.133 Uiso 1 1 calc R U . . .
H3B H 0.7141 0.3768 0.3877 0.133 Uiso 1 1 calc R U . . .
C4 C 0.7312(7) 0.2312(6) 0.3399(3) 0.163(3) Uani 1 1 d . . . . .
H4A H 0.8248 0.2327 0.3466 0.244 Uiso 1 1 calc R U . . .
H4B H 0.7063 0.2470 0.2852 0.244 Uiso 1 1 calc R U . . .
H4C H 0.6998 0.1637 0.3530 0.244 Uiso 1 1 calc R U . . .
C5 C 0.7888(4) 0.3257(3) 0.6511(2) 0.0819(11) Uani 1 1 d . . . . .
H5A H 0.7934 0.3171 0.7089 0.098 Uiso 1 1 calc R U . . .
H5B H 0.8202 0.2623 0.6277 0.098 Uiso 1 1 calc R U . . .
C6 C 0.8795(4) 0.4109(4) 0.6299(3) 0.0962(12) Uani 1 1 d . . . . .
H6A H 0.8482 0.4757 0.6510 0.115 Uiso 1 1 calc R U . . .
H6B H 0.8822 0.4170 0.5721 0.115 Uiso 1 1 calc R U . . .
C7 C 1.0151(5) 0.3882(5) 0.6649(3) 0.1177(16) Uani 1 1 d . . . . .
H7A H 1.0125 0.3884 0.7229 0.141 Uiso 1 1 calc R U . . .
H7B H 1.0410 0.3197 0.6483 0.141 Uiso 1 1 calc R U . . .
C8 C 1.1128(5) 0.4621(5) 0.6404(4) 0.143(2) Uani 1 1 d . . . . .
H8A H 1.1181 0.4607 0.5831 0.215 Uiso 1 1 calc R U . . .
H8B H 1.1963 0.4443 0.6647 0.215 Uiso 1 1 calc R U . . .
H8C H 1.0884 0.5300 0.6572 0.215 Uiso 1 1 calc R U . . .
C9 C 0.5878(4) 0.4317(3) 0.6645(2) 0.0823(10) Uani 1 1 d . . . . .
H9A H 0.6301 0.4934 0.6450 0.099 Uiso 1 1 calc R U . . .
H9B H 0.4963 0.4353 0.6472 0.099 Uiso 1 1 calc R U . . .
C10 C 0.5959(5) 0.4338(3) 0.7541(2) 0.1025(14) Uani 1 1 d . . . . .
H10A H 0.6870 0.4322 0.7725 0.123 Uiso 1 1 calc R U . . .
H10B H 0.5534 0.3729 0.7747 0.123 Uiso 1 1 calc R U . . .
C11 C 0.5317(6) 0.5286(4) 0.7862(3) 0.1271(18) Uani 1 1 d . . . . .
H11A H 0.5703 0.5890 0.7623 0.153 Uiso 1 1 calc R U . . .
H11B H 0.4396 0.5275 0.7703 0.153 Uiso 1 1 calc R U . . .
C12 C 0.5447(8) 0.5377(5) 0.8749(3) 0.154(2) Uani 1 1 d . . . . .
H12A H 0.5123 0.4761 0.8991 0.231 Uiso 1 1 calc R U . . .
H12B H 0.4952 0.5960 0.8922 0.231 Uiso 1 1 calc R U . . .
H12C H 0.6352 0.5470 0.8908 0.231 Uiso 1 1 calc R U . . .
C13 C 0.5827(4) 0.2395(3) 0.6483(2) 0.0876(12) Uani 1 1 d . . . . .
H13A H 0.6233 0.1834 0.6199 0.105 Uiso 1 1 calc R U . . .
H13B H 0.6000 0.2282 0.7051 0.105 Uiso 1 1 calc R U . . .
C14 C 0.4377(5) 0.2343(4) 0.6318(3) 0.1115(16) Uani 1 1 d D U . . .
H14A H 0.4199 0.2461 0.5750 0.134 Uiso 1 1 calc R U . . .
H14B H 0.3965 0.2895 0.6608 0.134 Uiso 1 1 calc R U . . .
C15 C 0.3757(9) 0.1332(6) 0.6547(5) 0.177(3) Uani 1 1 d D U . . .
H15A H 0.3987 0.1179 0.7103 0.213 Uiso 1 1 calc R U . . .
H15B H 0.2813 0.1394 0.6494 0.213 Uiso 1 1 calc R U . . .
C16 C 0.4185(14) 0.0492(7) 0.6046(7) 0.271(5) Uani 1 1 d D U . . .
H16A H 0.3458 0.0046 0.5917 0.406 Uiso 1 1 calc R U . . .
H16B H 0.4859 0.0108 0.6329 0.406 Uiso 1 1 calc R U . . .
H16C H 0.4521 0.0767 0.5561 0.406 Uiso 1 1 calc R U . . .
Cl1 Cl 0.85049(14) 0.33393(11) 0.90163(10) 0.1280(6) Uani 1 1 d . . . . .
Cl2 Cl 0.58927(16) 0.24914(14) 0.95840(12) 0.1583(8) Uani 1 1 d . . . . .
N1 N 0.6478(3) 0.3395(2) 0.62489(16) 0.0734(8) Uani 1 1 d . . . . .
O1 O 0.8185(3) 0.1295(2) 0.95863(16) 0.0984(9) Uani 1 1 d . . . . .
O2 O 0.7155(5) 0.1750(3) 0.82250(19) 0.1430(16) Uani 1 1 d . . . . .
P1 P 0.74944(11) 0.19950(9) 0.90447(6) 0.0815(4) 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 C2 1.484(6) . ?
C1 N1 1.525(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.537(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.522(8) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.493(6) . ?
C5 N1 1.502(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.513(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.453(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.497(5) . ?
C9 N1 1.507(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.501(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.487(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.500(6) . ?
C13 N1 1.516(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.510(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.450(10) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
Cl1 P1 2.0273(19) . ?
Cl2 P1 2.0052(18) . ?
O1 P1 1.446(3) . ?
O2 P1 1.435(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
C2 C1 N1 115.7(3) . . ?
C2 C1 H1A 108.4 . . ?
N1 C1 H1A 108.4 . . ?
C2 C1 H1B 108.4 . . ?
N1 C1 H1B 108.4 . . ?
H1A C1 H1B 107.4 . . ?
C1 C2 C3 109.2(4) . . ?
C1 C2 H2A 109.8 . . ?
C3 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
C3 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
C4 C3 C2 111.0(5) . . ?
C4 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 N1 116.1(3) . . ?
C6 C5 H5A 108.2 . . ?
N1 C5 H5A 108.2 . . ?
C6 C5 H5B 108.2 . . ?
N1 C5 H5B 108.2 . . ?
H5A C5 H5B 107.4 . . ?
C5 C6 C7 109.5(4) . . ?
C5 C6 H6A 109.8 . . ?
C7 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
C7 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
C8 C7 C6 113.2(5) . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 N1 116.4(3) . . ?
C10 C9 H9A 108.2 . . ?
N1 C9 H9A 108.2 . . ?
C10 C9 H9B 108.2 . . ?
N1 C9 H9B 108.2 . . ?
H9A C9 H9B 107.3 . . ?
C9 C10 C11 111.3(4) . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 C10 113.4(5) . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 N1 115.6(3) . . ?
C14 C13 H13A 108.4 . . ?
N1 C13 H13A 108.4 . . ?
C14 C13 H13B 108.4 . . ?
N1 C13 H13B 108.4 . . ?
H13A C13 H13B 107.4 . . ?
C13 C14 C15 114.5(5) . . ?
C13 C14 H14A 108.6 . . ?
C15 C14 H14A 108.6 . . ?
C13 C14 H14B 108.6 . . ?
C15 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C16 C15 C14 111.5(7) . . ?
C16 C15 H15A 109.3 . . ?
C14 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C5 N1 C9 111.7(3) . . ?
C5 N1 C13 104.4(3) . . ?
C9 N1 C13 112.0(3) . . ?
C5 N1 C1 111.3(3) . . ?
C9 N1 C1 106.2(3) . . ?
C13 N1 C1 111.3(3) . . ?
O2 P1 O1 123.5(2) . . ?
O2 P1 Cl2 109.1(2) . . ?
O1 P1 Cl2 107.97(15) . . ?
O2 P1 Cl1 105.86(18) . . ?
O1 P1 Cl1 108.46(15) . . ?
Cl2 P1 Cl1 99.25(9) . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
N1 C1 C2 C3 -177.3(3) . . . . ?
C1 C2 C3 C4 178.5(4) . . . . ?
N1 C5 C6 C7 176.5(4) . . . . ?
C5 C6 C7 C8 174.2(5) . . . . ?
N1 C9 C10 C11 -179.4(4) . . . . ?
C9 C10 C11 C12 -176.2(5) . . . . ?
N1 C13 C14 C15 179.2(5) . . . . ?
C13 C14 C15 C16 -67.1(10) . . . . ?
C6 C5 N1 C9 -63.0(4) . . . . ?
C6 C5 N1 C13 175.7(3) . . . . ?
C6 C5 N1 C1 55.5(4) . . . . ?
C10 C9 N1 C5 -55.7(4) . . . . ?
C10 C9 N1 C13 61.1(5) . . . . ?
C10 C9 N1 C1 -177.2(4) . . . . ?
C14 C13 N1 C5 177.5(4) . . . . ?
C14 C13 N1 C9 56.5(5) . . . . ?
C14 C13 N1 C1 -62.3(5) . . . . ?
C2 C1 N1 C5 56.8(4) . . . . ?
C2 C1 N1 C9 178.6(3) . . . . ?
C2 C1 N1 C13 -59.2(4) . . . . ?
 
_refine_diff_density_max    0.834
_refine_diff_density_min   -0.295
_refine_diff_density_rms    0.055



