From the parent phosphinidene-carbene adduct NHC[double bond, length as m-dash]PH to cationic P4-rings and P2-cycloaddition products.
Beil, Andreas; Gilliard, Robert J.; Grützmacher, Hansjörg; Dalton transactions (Cambridge, England : 2003) 45 (2016) 2044–2052; doi:10.1039/c5dt03014e

data_7036647
_publ_section_title
;
 From the parent phosphinidene-carbene adduct NHC[double bond, length as
 m-dash]PH to cationic P4-rings and P2-cycloaddition products.
;
_journal_issue                   5
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2044
_journal_page_last               2052
_journal_paper_doi               10.1039/c5dt03014e
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety         'C33 H50 Cl N3 P2'
_chemical_formula_sum            'C33 H50 Cl N3 P2'
_chemical_formula_weight         586.15
_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-07-14
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-07-28 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;
_cell_angle_alpha                83.6921(8)
_cell_angle_beta                 82.8084(8)
_cell_angle_gamma                62.1884(8)
_cell_formula_units_Z            2
_cell_length_a                   10.4571(2)
_cell_length_b                   10.8862(2)
_cell_length_c                   16.6912(3)
_cell_measurement_reflns_used    6996
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      2.21
_cell_volume                     1664.52(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 8.33
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'fixed chi three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART Apex2'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25555
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.114
_diffrn_reflns_theta_min         1.232
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  0.9443
_exptl_absorpt_correction_T_min  0.8509
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0462 before and 0.0424 after correction.
The Ratio of minimum to maximum transmission is 0.9011.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane'
_exptl_crystal_size_max          0.297
_exptl_crystal_size_mid          0.176
_exptl_crystal_size_min          0.083
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         7359
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0399
_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/[\s^2^(Fo^2^)+(0.0286P)^2^+0.8214P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0867
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5736
_reflns_number_total             7359
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5dt03014e2.cif
_cod_data_source_block           2b
_cod_depositor_comments
'Adding full bibliography for 7036646--7036654.cif.'
_cod_database_code               7036647
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.933
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.016) H3(0.016) H6(0.021) H7(0.024) H8(0.021) H10(0.019)
 H11A(0.049) H11B(0.049) H11C(0.049) H12A(0.041) H12B(0.041) H12C(0.041)
 H13(0.02) H15A(0.041) H15B(0.041) H15C(0.041) H14A(0.03) H14B(0.03) H14C(0.03)
 H20(0.02) H19(0.024) H18(0.022) H22(0.019) H23A(0.041) H23B(0.041) H23C(0.041)
 H24A(0.037) H24B(0.037) H24C(0.037) H25(0.018) H27A(0.034) H27B(0.034)
 H27C(0.034) H26A(0.031) H26B(0.031) H26C(0.031) H31(0.02) H32A(0.04)
 H32B(0.04) H32C(0.04) H33A(0.039) H33B(0.039) H33C(0.039) H28(0.021)
 H30A(0.037) H30B(0.037) H30C(0.037) H29A(0.039) H29B(0.039) H29C(0.039)
 Fixed X: H2(0.8124) H3(0.9185) H6(0.9597) H7(0.7222) H8(0.5326) H10(1.0739)
 H11A(1.1678) H11B(1.2571) H11C(1.1097) H12A(1.0945) H12B(1.2476) H12C(1.1463)
 H13(0.5696) H15A(0.4373) H15B(0.3943) H15C(0.5516) H14A(0.4472) H14B(0.3363)
 H14C(0.3625) H20(1.312) H19(1.1756) H18(0.9284) H22(0.7211) H23A(0.6897)
 H23B(0.5565) H23C(0.6714) H24A(0.784) H24B(0.6199) H24C(0.744) H25(1.1776)
 H27A(1.2313) H27B(1.3658) H27C(1.371) H26A(1.423) H26B(1.4157) H26C(1.315)
 H31(0.8938) H32A(0.7463) H32B(0.8347) H32C(0.6893) H33A(1.0611) H33B(1.0606)
 H33C(0.98) H28(0.7439) H30A(0.5073) H30B(0.5048) H30C(0.5169) H29A(0.8652)
 H29B(0.719) H29C(0.7246)
 Fixed Y: H2(0.6442) H3(0.5493) H6(0.4087) H7(0.5397) H8(0.6175) H10(0.2994)
 H11A(0.2297) H11B(0.1484) H11C(0.144) H12A(0.5036) H12B(0.3722) H12C(0.4603)
 H13(0.5355) H15A(0.7967) H15B(0.7718) H15C(0.7594) H14A(0.4608) H14B(0.582)
 H14C(0.6168) H20(0.0328) H19(0.0118) H18(0.1578) H22(0.433) H23A(0.214)
 H23B(0.3529) H23C(0.2445) H24A(0.4865) H24B(0.5103) H24C(0.3741) H25(0.2729)
 H27A(0.043) H27B(0.0718) H27C(-0.0176) H26A(0.1475) H26B(0.2351) H26C(0.3108)
 H31(-0.069) H32A(-0.1778) H32B(-0.2506) H32C(-0.1062) H33A(-0.1137) H33B(-
 0.2556) H33C(-0.1785) H28(-0.0315) H30A(0.2285) H30B(0.1316) H30C(0.0795)
 H29A(0.0935) H29B(0.1368) H29C(0.2371)
 Fixed Z: H2(0.1843) H3(0.0512) H6(0.472) H7(0.5232) H8(0.441) H10(0.2685)
 H11A(0.4282) H11B(0.3494) H11C(0.3845) H12A(0.2715) H12B(0.2869) H12C(0.3611)
 H13(0.2336) H15A(0.3074) H15B(0.2242) H15C(0.2295) H14A(0.3428) H14B(0.2859)
 H14C(0.3712) H20(-0.0259) H19(-0.1179) H18(-0.1156) H22(0.0192) H23A(-0.0416)
 H23B(-0.0083) H23C(0.0519) H24A(-0.1177) H24B(-0.1054) H24C(-0.1466)
 H25(0.1315) H27A(0.1809) H27B(0.1887) H27C(0.1173) H26A(0.0167) H26B(0.0896)
 H26C(0.0167) H31(0.2647) H32A(0.3834) H32B(0.3021) H32C(0.2973) H33A(0.3579)
 H33B(0.3417) H33C(0.423) H28(0.4617) H30A(0.4182) H30B(0.4971) H30C(0.4092)
 H29A(0.4879) H29B(0.5462) H29C(0.4697)
;
_shelx_res_checksum              69872
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'