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_7036646
_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 H41 Cl N2 P2'
_chemical_formula_sum            'C33 H41 Cl N2 P2'
_chemical_formula_weight         563.07
_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
_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
_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                90
_cell_angle_beta                 93.0570(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0682(3)
_cell_length_b                   12.4824(3)
_cell_length_c                   24.4361(6)
_cell_measurement_reflns_used    9667
_cell_measurement_temperature    102
_cell_measurement_theta_max      78.91
_cell_measurement_theta_min      3.98
_cell_volume                     3066.64(14)
_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      102.0
_diffrn_detector                 'Bruker Photon 100 area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  ETH_LAC_PhotonD8_Cu
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'double mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            65434
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         78.992
_diffrn_reflns_theta_min         3.623
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.262
_exptl_absorpt_correction_T_max  0.8289
_exptl_absorpt_correction_T_min  0.6719
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0808 before and 0.0672 after correction.
The Ratio of minimum to maximum transmission is 0.8106.
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    1.220
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.097
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         6607
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0559P)^2^+2.8301P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1130
_refine_ls_wR_factor_ref         0.1175
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5838
_reflns_number_total             6607
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5dt03014e2.cif
_cod_data_source_block           2a
_cod_depositor_comments
'Adding full bibliography for 7036646--7036654.cif.'
_cod_database_code               7036646
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.021) H3(0.022) H22(0.025) H6(0.026) H8(0.025) H10(0.024)
 H13(0.023) H29(0.026) H18(0.028) H7(0.029) H33(0.03) H25(0.028) H30(0.028)
 H23A(0.041) H23B(0.041) H23C(0.041) H20(0.03) H11A(0.04) H11B(0.04) H11C(0.04)
 H19(0.032) H31(0.032) H12A(0.043) H12B(0.043) H12C(0.043) H26A(0.046)
 H26B(0.046) H26C(0.046) H24A(0.046) H24B(0.046) H24C(0.046) H32(0.037)
 H27A(0.054) H27B(0.054) H27C(0.054) H15A(0.074) H15B(0.074) H15C(0.074)
 H14A(0.074) H14B(0.074) H14C(0.074)
 Fixed X: H2(1.0793) H3(1.1604) H22(1.0664) H6(0.6777) H8(0.7664) H10(0.8041)
 H13(0.8893) H29(0.4396) H18(1.0881) H7(0.6748) H33(0.4414) H25(0.8488)
 H30(0.2985) H23A(0.9665) H23B(0.9883) H23C(0.8775) H20(0.9309) H11A(0.6192)
 H11B(0.6472) H11C(0.5747) H19(1.029) H31(0.2316) H12A(0.9701) H12B(0.8869)
 H12C(0.8593) H26A(0.6763) H26B(0.6749) H26C(0.7353) H24A(1.2738) H24B(1.2288)
 H24C(1.2118) H32(0.3019) H27A(0.9555) H27B(0.8898) H27C(1.0263) H15A(1.0422)
 H15B(1.0766) H15C(1.0846) H14A(0.7232) H14B(0.855) H14C(0.8255)
 Fixed Y: H2(0.1629) H3(0.3267) H22(0.2502) H6(-0.0469) H8(-0.1343)
 H10(0.2218) H13(0.1193) H29(0.3668) H18(0.4962) H7(-0.1738) H33(0.4115)
 H25(0.4687) H30(0.5134) H23A(0.3182) H23B(0.1958) H23C(0.2665) H20(0.6849)
 H11A(0.0943) H11B(0.2192) H11C(0.1797) H19(0.6651) H31(0.6122) H12A(0.1113)
 H12B(0.1685) H12C(0.0456) H26A(0.546) H26B(0.5939) H26C(0.6629) H24A(0.3225)
 H24B(0.2258) H24C(0.3469) H32(0.5597) H27A(0.6802) H27B(0.6141) H27C(0.574)
 H15A(-0.0723) H15B(0.0263) H15C(0.0407) H14A(0.0088) H14B(0.0136) H14C(-0.0894)
 Fixed Z: H2(0.5555) H3(0.6031) H22(0.7148) H6(0.4843) H8(0.6411) H10(0.4978)
 H13(0.6871) H29(0.6834) H18(0.7916) H7(0.5541) H33(0.5194) H25(0.5767)
 H30(0.6904) H23A(0.8169) H23B(0.8001) H23C(0.7675) H20(0.6707) H11A(0.4324)
 H11B(0.4236) H11C(0.4768) H19(0.7585) H31(0.6123) H12A(0.4622) H12B(0.4128)
 H12C(0.4269) H26A(0.6261) H26B(0.5653) H26C(0.6159) H24A(0.7481) H24B(0.7859)
 H24C(0.8058) H32(0.5266) H27A(0.5693) H27B(0.5186) H27C(0.5484) H15A(0.6814)
 H15B(0.7216) H15C(0.6568) H14A(0.723) H14B(0.7625) H14C(0.7248)
;
_shelx_res_checksum              90232
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'