#------------------------------------------------------------------------------
#$Date: 2016-02-05 01:58:02 +0200 (Fri, 05 Feb 2016) $
#$Revision: 176072 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/65/7036598.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7036598
loop_
_publ_author_name
'Klöcker, Hans'
'Layh, Marcus'
'Hepp, Alexander'
'Uhl, Werner'
_publ_section_title
;
 Hydroalumination of alkynyl-aminophosphines as a promising tool for the
 synthesis of unusual phosphines: P-N bond activation, a transient
 phosphaallene, a zwitterionic AlP2C2 heterocycle and a masked Al/P-based
 frustrated Lewis pair.
;
_journal_issue                   5
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2031
_journal_page_last               2043
_journal_paper_doi               10.1039/c5dt02825f
_journal_volume                  45
_journal_year                    2016
_chemical_formula_sum            'C9 H11 Cl2 P'
_chemical_formula_weight         221.05
_chemical_name_systematic
;
 ?
;
_chemical_properties_physical    'Air-sensitive, Hygroscopic'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-07-22 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.8230(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1445(3)
_cell_length_b                   7.1178(3)
_cell_length_c                   18.4060(8)
_cell_measurement_reflns_used    6458
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      30.088
_cell_measurement_theta_min      2.574
_cell_volume                     1044.38(7)
_computing_cell_refinement       'Bruker SAINT+'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_laue_measured_fraction_full 0.985
_diffrn_reflns_laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10452
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.093
_diffrn_reflns_theta_min         2.573
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.719
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5786
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         3026
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0357
_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)+(0.0466P)²+0.6246P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.0988
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2710
_reflns_number_total             3026
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5dt02825f2.cif
_cod_data_source_block           sad
_cod_depositor_comments
'Adding full bibliography for 7036598--7036603.cif.'
_cod_database_code               7036598
_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.
;
_shelx_estimated_absorpt_t_min   0.706
_shelx_estimated_absorpt_t_max   0.894
_shelxl_version_number           2013-4
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'
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
P1 P 0.97028(5) 0.67927(6) 0.18167(2) 0.02741(11) Uani 1 1 d . .
Cl1 Cl 1.16895(5) 0.82670(6) 0.24506(2) 0.03354(12) Uani 1 1 d . .
Cl2 Cl 1.07383(6) 0.60130(6) 0.09138(2) 0.03628(12) Uani 1 1 d . .
C1 C 0.82681(18) 0.8661(2) 0.14277(8) 0.0224(3) Uani 1 1 d . .
C2 C 0.6623(2) 0.8390(2) 0.15400(8) 0.0263(3) Uani 1 1 d . .
C21 C 0.6130(3) 0.6749(3) 0.19734(12) 0.0408(4) Uani 1 1 d . .
H21A H 0.4939 0.6764 0.1942 0.049 Uiso 1 1 calc R U
H21B H 0.6695 0.6848 0.2484 0.049 Uiso 1 1 calc R U
H21C H 0.6445 0.5594 0.1769 0.049 Uiso 1 1 calc R U
C3 C 0.53883(19) 0.9700(2) 0.12561(9) 0.0282(3) Uani 1 1 d . .
H3 H 0.4269 0.9510 0.1332 0.034 Uiso 1 1 calc R U
C4 C 0.57278(19) 1.1272(2) 0.08666(8) 0.0263(3) Uani 1 1 d . .
C41 C 0.4361(2) 1.2638(3) 0.05486(10) 0.0343(4) Uani 1 1 d . .
H41A H 0.4847 1.3737 0.0375 0.041 Uiso 1 1 calc R U
H41B H 0.3761 1.2989 0.0925 0.041 Uiso 1 1 calc R U
H41C H 0.3603 1.2060 0.0142 0.041 Uiso 1 1 calc R U
C5 C 0.73630(19) 1.1534(2) 0.07701(8) 0.0250(3) Uani 1 1 d . .
H5 H 0.7613 1.2623 0.0505 0.030 Uiso 1 1 calc R U
C6 C 0.86518(18) 1.0275(2) 0.10448(8) 0.0221(3) Uani 1 1 d . .
C61 C 1.03860(19) 1.0761(2) 0.09386(9) 0.0270(3) Uani 1 1 d . .
H61A H 1.0311 1.1694 0.0557 0.032 Uiso 1 1 calc R U
H61B H 1.0917 0.9654 0.0797 0.032 Uiso 1 1 calc R U
H61C H 1.1037 1.1244 0.1395 0.032 Uiso 1 1 calc R U
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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 P1 Cl1 102.47(5)
C1 P1 Cl2 102.29(5)
Cl1 P1 Cl2 100.75(3)
C2 C1 C6 119.80(13)
C2 C1 P1 113.33(11)
C6 C1 P1 126.87(11)
C3 C2 C1 119.25(14)
C3 C2 C21 117.74(15)
C1 C2 C21 123.00(15)
C2 C21 H21A 109.5
C2 C21 H21B 109.5
H21A C21 H21B 109.5
C2 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C4 C3 C2 121.94(14)
C4 C3 H3 119.0
C2 C3 H3 119.0
C3 C4 C5 118.13(14)
C3 C4 C41 120.85(14)
C5 C4 C41 121.01(15)
C4 C41 H41A 109.5
C4 C41 H41B 109.5
H41A C41 H41B 109.5
C4 C41 H41C 109.5
H41A C41 H41C 109.5
H41B C41 H41C 109.5
C4 C5 C6 122.46(14)
C4 C5 H5 118.8
C6 C5 H5 118.8
C5 C6 C1 118.40(13)
C5 C6 C61 117.52(13)
C1 C6 C61 124.04(13)
C6 C61 H61A 109.5
C6 C61 H61B 109.5
H61A C61 H61B 109.5
C6 C61 H61C 109.5
H61A C61 H61C 109.5
H61B C61 H61C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 C1 1.8174(15)
P1 Cl1 2.0753(6)
P1 Cl2 2.0871(6)
C1 C2 1.410(2)
C1 C6 1.416(2)
C2 C3 1.392(2)
C2 C21 1.515(2)
C21 H21A 0.9599
C21 H21B 0.9599
C21 H21C 0.9599
C3 C4 1.387(2)
C3 H3 0.9600
C4 C5 1.392(2)
C4 C41 1.503(2)
C41 H41A 0.9599
C41 H41B 0.9599
C41 H41C 0.9599
C5 C6 1.394(2)
C5 H5 0.9600
C6 C61 1.505(2)
C61 H61A 0.9599
C61 H61B 0.9599
C61 H61C 0.9599
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
Cl1 P1 C1 C2 -128.31(11)
Cl2 P1 C1 C2 127.59(11)
Cl1 P1 C1 C6 51.51(14)
Cl2 P1 C1 C6 -52.59(14)
C6 C1 C2 C3 1.5(2)
P1 C1 C2 C3 -178.70(12)
C6 C1 C2 C21 -177.17(16)
P1 C1 C2 C21 2.7(2)
C1 C2 C3 C4 -0.2(2)
C21 C2 C3 C4 178.53(16)
C2 C3 C4 C5 -0.8(2)
C2 C3 C4 C41 178.38(15)
C3 C4 C5 C6 0.5(2)
C41 C4 C5 C6 -178.69(15)
C4 C5 C6 C1 0.8(2)
C4 C5 C6 C61 -176.99(14)
C2 C1 C6 C5 -1.8(2)
P1 C1 C6 C5 178.44(11)
C2 C1 C6 C61 175.86(14)
P1 C1 C6 C61 -3.9(2)
