An anionic nucleophilic d(4) carbyne complex.
Hill, Anthony F.; Kong, Richard Y.; Chemical communications (Cambridge, England) 53 (2017) 2032–2035; doi:10.1039/c6cc09718a

data_7119546
_publ_section_title
;
 An anionic nucleophilic d(4) carbyne complex.
;
_journal_issue                   12
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2032
_journal_page_last               2035
_journal_paper_doi               10.1039/c6cc09718a
_journal_volume                  53
_journal_year                    2017
_chemical_formula_moiety         'C33 H57 Cl O2 P2 W'
_chemical_formula_sum            'C33 H57 Cl O2 P2 W'
_chemical_formula_weight         767.02
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-06-25
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-11-08 deposited with the CCDC.
2016-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.8393(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.90249(14)
_cell_length_b                   14.24490(18)
_cell_length_c                   22.5025(3)
_cell_measurement_reflns_used    21562
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      72.2980
_cell_measurement_theta_min      3.6460
_cell_volume                     3462.09(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
  1 omega   41.00   97.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254   57.0000  -90.0000 56

  2 omega   24.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254   77.0000  150.0000 80

  3 omega  -22.00   23.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254  -38.0000  -90.0000 45

  4 omega    1.00   72.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254  -99.0000    0.0000 71

  5 omega    5.00   45.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254  -99.0000  -30.0000 40

  6 omega  -30.00   53.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
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  7 omega   37.00   68.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
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  8 omega   39.00  102.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
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  9 omega  -17.00   14.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0254  -57.0000 -150.0000 31

 10 omega   42.00   89.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
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 11 omega   37.00  102.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -120.0000 65

 12 omega  120.00  165.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 45

 13 omega   42.00   85.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 14 omega   58.00   84.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  150.0000 26

 15 omega   40.00   75.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 35

 16 omega   45.00   75.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000  120.0000 30

 17 omega   42.00   80.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 18 omega   70.00  114.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 19 omega   69.00   95.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 26

 20 omega   90.00  121.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 21 omega   62.00  105.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 22 omega   69.00  106.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 37

 23 omega  105.00  146.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 24 omega  153.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 25 omega   60.00   85.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  120.0000 25

 26 omega   60.00   86.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -60.0000 26

 27 omega   90.00  124.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 28 omega   53.00   78.00   1.0000   16.0000
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 29 omega   80.00  164.00   1.0000   16.0000
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 30 omega   98.00  125.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 31 omega   82.00  107.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 32 omega   62.00   89.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 33 omega   44.00   80.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 36

 34 omega  101.00  126.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 36 omega   71.00   97.00   1.0000   16.0000
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    -      108.0000   15.0000 -150.0000 26

 37 omega   38.00   71.00   1.0000   16.0000
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 38 omega   76.00  114.00   1.0000   16.0000
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 39 omega   48.00   75.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 40 omega  147.00  172.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 41 omega   59.00   90.00   1.0000   16.0000
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 42 omega   45.00   86.00   1.0000   16.0000
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 43 omega   79.00  116.00   1.0000   16.0000
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 44 omega  119.00  149.00   1.0000   16.0000
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 45 omega  148.00  174.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 46 omega  116.00  145.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 29

 47 omega   54.00   91.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 37

 48 omega   52.00   93.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 49 omega  143.00  169.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 50 omega   65.00   91.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 51 omega   71.00  121.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 52 omega   46.00   76.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 53 omega  113.00  145.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 54 omega   49.00   78.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 55 omega  120.00  145.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 56 omega   69.00   94.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   60.0000 25

 57 omega  111.00  144.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   60.0000 33

 58 omega   41.00   90.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 59 omega   68.00  113.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 60 omega   44.00   90.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 46

 61 omega   71.00   97.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -95.0000   30.0000 26

 62 omega  102.00  142.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 40

 63 omega  100.00  131.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 64 omega  118.00  144.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 65 omega   82.00  110.00   1.0000   16.0000
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 66 omega   41.00   66.00   1.0000   16.0000
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 67 omega   92.00  118.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   90.0000 26

 68 omega   86.00  112.00   1.0000   16.0000
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    -      108.0000  -77.0000 -180.0000 26

 69 omega   77.00  103.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
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 70 omega   49.00   75.00   1.0000   16.0000
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 71 omega  100.00  134.00   1.0000   16.0000
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 72 omega   92.00  119.00   1.0000   16.0000
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 73 omega   73.00  107.00   1.0000   16.0000
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 74 omega   41.00   75.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -81.0000  137.7715 34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_orient_matrix_UB_11      -0.0656321000
_diffrn_orient_matrix_UB_12      0.0006121000
_diffrn_orient_matrix_UB_13      -0.0651273000
_diffrn_orient_matrix_UB_21      0.0142948000
_diffrn_orient_matrix_UB_22      -0.1073961000
_diffrn_orient_matrix_UB_23      -0.0030221000
_diffrn_orient_matrix_UB_31      -0.1259205000
_diffrn_orient_matrix_UB_32      -0.0124880000
_diffrn_orient_matrix_UB_33      0.0228709000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            45483
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.434
_diffrn_reflns_theta_min         3.682
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.962
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_description       plate
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.1216
_exptl_crystal_size_mid          0.0731
_exptl_crystal_size_min          0.0175
_refine_diff_density_max         4.354
_refine_diff_density_min         -2.063
_refine_diff_density_rms         0.178
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         6760
_refine_ls_number_restraints     173
_refine_ls_restrained_S_all      1.145
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0613
_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^)+(0.0301P)^2^+52.3005P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1507
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6335
_reflns_number_total             6760
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc09718a2.cif
_cod_data_source_block           Compound_5a
_cod_depositor_comments
'Adding full bibliography for 7119543--7119548.cif.'
_cod_database_code               7119546
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Restrained distances
 C42-C43 = C44-C45
 1.53 with sigma of 0.01
 C46-C45
 1.53 with sigma of 0.01
 C24-H24A
 0.95 with sigma of 0.01
 C53-H53A
 0.95 with sigma of 0.01
3. Rigid bond restraints
 C31, C32, C33, C34, C35, C36
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C41, C42, C43, C44, C45, C46
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C61, C62, C63, C64, C65, C66
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C21, C22, C23, C24, C25, C26
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C51, C52, C53, C54, C55, C56
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Uiso/Uaniso restraints and constraints
C31 \\sim C32 \\sim C33 \\sim C34 \\sim C35 \\sim C36: within 1.7A with sigma
of 0.02 and sigma for terminal atoms of 0.04
C41 \\sim C42 \\sim C43 \\sim C44 \\sim C45 \\sim C46: within 1.7A with sigma
of 0.02 and sigma for terminal atoms of 0.04
C51 \\sim C52 \\sim C53 \\sim C54 \\sim C55 \\sim C56: within 1.7A with sigma
of 0.02 and sigma for terminal atoms of 0.04
Uanis(W1) = Uanis(C1)
5. Others
 Fixed Sof: C31(0.5) H31(0.5) C32(0.5) H32A(0.5) H32B(0.5) C33(0.5) H33A(0.5)
 H33B(0.5) C34(0.5) H34A(0.5) H34B(0.5) C35(0.5) H35A(0.5) H35B(0.5) C36(0.5)
 H36A(0.5) H36B(0.5) C41(0.5) H41(0.5) C42(0.5) H42A(0.5) H42B(0.5) C43(0.5)
 H43A(0.5) H43B(0.5) C44(0.5) H44A(0.5) H44B(0.5) C45(0.5) H45A(0.5) H45B(0.5)
 C46(0.5) H46A(0.5) H46B(0.5) C51(0.5) H51(0.5) C52(0.5) H52A(0.5) H52B(0.5)
 C53(0.5) H53A(0.5) H53B(0.5) C54(0.5) H54A(0.5) H54B(0.5) C55(0.5) H55A(0.5)
 H55B(0.5) C56(0.5) H56A(0.5) H56B(0.5) C61(0.5) H61(0.5) C62(0.5) H62A(0.5)
 H62B(0.5) C63(0.5) H63A(0.5) H63B(0.5) C64(0.5) H64A(0.5) H64B(0.5) C65(0.5)
 H65A(0.5) H65B(0.5) C66(0.5) H66A(0.5) H66B(0.5)
6.a Ternary CH refined with riding coordinates:
 C11(H11), C21(H21), C31(H31), C41(H41), C51(H51), C61(H61)
6.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B),
 C15(H15A,H15B), C16(H16A,H16B), C22(H22A,H22B), C23(H23A,H23B), C25(H25A,H25B),
  C26(H26A,H26B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,
 H35B), C36(H36A,H36B), C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B),
 C45(H45A,H45B), C46(H46A,H46B), C52(H52A,H52B), C54(H54A,H54B), C55(H55A,H55B),
  C56(H56A,H56B), C62(H62A,H62B), C63(H63A,H63B), C64(H64A,H64B), C65(H65A,
 H65B), C66(H66A,H66B)
6.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_shelx_res_checksum              57533
_shelx_hkl_checksum              62404
_ins_header
;
TITL RK01_scaled in P2(1)/n 
REM P2(1)/n (#14 in standard setting)
CELL 1.54184  10.902495  14.244903  22.502518  90.0000  97.8393  90.0000
ZERR    4.00   0.000143   0.000180   0.000301   0.0000   0.0013   0.0000
LATT  1
SYMM -x+1/2, y+1/2,-z+1/2 
SFAC C H O P Cl W
UNIT 132.00 228.00 8.00 8.00 4.00 4.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'