Synthesis of P2C2O2 and P2CO via NHC-Mediated Coupling of the Phosphaethynolate Anion
Gilliard, Robert J.; Suter, Riccardo; Schrader, Erik; Benkö, Zoltan; Rheingold, Arnold L.; Grützmacher, Hansjörg; Protasiewicz, John D.; Chem. Commun.  (2017) –; doi:10.1039/C7CC07654A

data_7120835
_publ_section_title
;
 Synthesis of P2C2O2 and P2CO via NHC-Mediated Coupling of the
 Phosphaethynolate Anion
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC07654A
_journal_year                    2017
_chemical_formula_moiety         'C55 H72 N4 O P2, C4 H8 O2'
_chemical_formula_sum            'C59 H80 N4 O3 P2'
_chemical_formula_weight         955.21
_chemical_properties_physical
', Air-sensitive,Moisture-sensitive,Oxygen-sensitive'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-06-26
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-03-09 deposited with the CCDC.
2017-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4060(5)
_cell_length_b                   14.2364(4)
_cell_length_c                   31.2334(17)
_cell_measurement_reflns_used    3218
_cell_measurement_temperature    105.79(12)
_cell_measurement_theta_max      25.4240
_cell_measurement_theta_min      3.2740
_cell_volume                     5516.3(4)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.'
_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_environment      N~2~
_diffrn_ambient_temperature      105.79(12)
_diffrn_detector                 'Oxford Diffraction Sapphire 3'
_diffrn_detector_area_resol_mean 8.26
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.944
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_details
;
  1 omega   20.00   97.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6990   77.0000 -120.0000 77

  2 omega    4.00   46.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6990  -19.0000  -60.0000 42

  3 omega    5.00   65.00   1.0000  120.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6990   57.0000   30.0000 60
;
_diffrn_measurement_device       'kappa-stage diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur S'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_UB_11      -0.0155077000
_diffrn_orient_matrix_UB_12      -0.0392356000
_diffrn_orient_matrix_UB_13      -0.0125786000
_diffrn_orient_matrix_UB_21      0.0547603000
_diffrn_orient_matrix_UB_22      -0.0136810000
_diffrn_orient_matrix_UB_23      -0.0017923000
_diffrn_orient_matrix_UB_31      -0.0051212000
_diffrn_orient_matrix_UB_32      -0.0274704000
_diffrn_orient_matrix_UB_33      0.0188436000
_diffrn_radiation_monochromator  'focusing graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0765
_diffrn_reflns_Laue_measured_fraction_full 0.944
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            13695
_diffrn_reflns_point_group_measured_fraction_full 0.883
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_theta_full        23.253
_diffrn_reflns_theta_max         23.253
_diffrn_reflns_theta_min         2.862
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Green
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.497
_refine_diff_density_min         -0.702
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 1818 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     599
_refine_ls_number_reflns         6985
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0790
_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/[\s^2^(Fo^2^)+(0.1250P)^2^+6.8380P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2062
_refine_ls_wR_factor_ref         0.2221
_reflns_Friedel_coverage         0.672
_reflns_Friedel_fraction_full    0.805
_reflns_Friedel_fraction_max     0.805
_reflns_number_gt                5839
_reflns_number_total             6985
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7cc07654a2.cif
_cod_data_source_block           new_richy
_cod_original_cell_volume        5516.4(4)
_cod_database_code               7120835
_chemical_oxdiff_formula         C20H20P2N4O2
_reflns_odcompleteness_completeness 93.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Uiso/Uaniso restraints and constraints
Uanis(O2) = Uanis(C59) = Uanis(C58) = Uanis(C57) = Uanis(O3) = Uanis(C56)
Uanis(C56) = Uanis(C59) = Uanis(O2) = Uanis(C58) = Uanis(C57) = Uanis(O3)
3.a Ternary CH refined with riding coordinates:
 C53(H53), C14(H14), C50(H50), C26(H26), C23(H23), C11(H11), C38(H38), C41(H41)
3.b Secondary CH2 refined with riding coordinates:
 C59(H59A,H59B), C56(H56A,H56B), C58(H58A,H58B), C57(H57A,H57B)
3.c Aromatic/amide H refined with riding coordinates:
 C31(H31), C3(H3), C46(H46), C4(H4), C30(H30), C21(H21), C7(H7), C48(H48),
 C9(H9), C35(H35), C47(H47), C20(H20), C36(H36), C8(H8), C19(H19), C34(H34)
3.d Idealised Me refined as rotating group:
 C54(H54A,H54B,H54C), C25(H25A,H25B,H25C), C52(H52A,H52B,H52C), C51(H51A,H51B,
 H51C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C24(H24A,H24B,H24C), C55(H55A,
 H55B,H55C), C28(H28A,H28B,H28C), C39(H39A,H39B,H39C), C40(H40A,H40B,H40C),
 C12(H12A,H12B,H12C), C42(H42A,H42B,H42C), C13(H13A,H13B,H13C), C43(H43A,H43B,
 H43C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              6769
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'