Tetrel and pnictogen functionalised propargylidynes.
Manzano, Richard A.; Hill, Anthony F.; Georgelin, Rosemary L.; Chemical communications (Cambridge, England) 56 (2020) 14597–14600; doi:10.1039/d0cc06196d

data_7127722
_publ_section_title
;
 Tetrel and pnictogen functionalised propargylidynes.
;
_journal_issue                   93
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              14597
_journal_page_last               14600
_journal_paper_doi               10.1039/d0cc06196d
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C115 H110 Ag3 B2 N12 O4 P6 W2, C7 H8, N O3'
_chemical_formula_sum            'C122 H118 Ag3 B2 N13 O7 P6 W2'
_chemical_formula_weight         2777.04
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc260tkm
_audit_creation_date             2020-09-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132)
;
_audit_update_record
;
2020-09-12 deposited with the CCDC.	2020-10-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.310(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3770(4)
_cell_length_b                   30.6356(7)
_cell_length_c                   28.8107(16)
_cell_measurement_reflns_used    6546
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      66.7800
_cell_measurement_theta_min      2.8700
_cell_volume                     13429.7(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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 0.992
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -105.00 -36.00   1.00   40.00    --  -35.78 -38.00-150.00   69
  2  \w    -51.00  32.00   1.00   40.00    --  -35.78  57.00-180.00   83
  3  \w     27.00  77.00   1.00   40.00    --   35.78-125.00  30.00   50
  4  \w     35.00 103.00   1.00   40.00    --   35.78  57.00 120.00   68
  5  \w     16.00  63.00   1.00   40.00    --   35.78 -99.00-120.00   47
  6  \w     44.00 108.00   1.00   70.00    --  107.33 -95.00   0.00   64
  7  \w     50.00 129.00   1.00   70.00    --  107.33 -30.00 150.00   79
  8  \w     40.00 134.00   1.00   70.00    --  107.33 -77.00 120.00   94
  9  \w     38.00  93.00   1.00   70.00    --  107.33 -95.00  90.00   55
 10  \w     69.00 171.00   1.00   70.00    --  107.33  15.00   0.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0020411000
_diffrn_orient_matrix_UB_12      -0.0101900000
_diffrn_orient_matrix_UB_13      0.0525250000
_diffrn_orient_matrix_UB_21      -0.1012146000
_diffrn_orient_matrix_UB_22      -0.0001186000
_diffrn_orient_matrix_UB_23      -0.0068154000
_diffrn_orient_matrix_UB_31      -0.0001148000
_diffrn_orient_matrix_UB_32      -0.0492272000
_diffrn_orient_matrix_UB_33      -0.0108931000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.1165
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            42754
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.904
_diffrn_reflns_theta_min         2.117
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.624
_exptl_absorpt_correction_T_max  0.61617
_exptl_absorpt_correction_T_min  0.58658
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Spherical absorption correction
 using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       needle
_exptl_crystal_F_000             5544
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.021
_exptl_crystal_size_rad          0.100
_refine_diff_density_max         1.660
_refine_diff_density_min         -1.512
_refine_diff_density_rms         0.163
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1381
_refine_ls_number_reflns         25391
_refine_ls_number_restraints     605
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1557
_refine_ls_R_factor_gt           0.1040
_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^)+(0.0632P)^2^+248.4265P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2215
_refine_ls_wR_factor_ref         0.2481
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14972
_reflns_number_total             25391
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc06196d2.cif
_cod_data_source_block           Compound_11
_cod_database_code               7127722
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C65 H66 Ag3 B2 N12 O4 P2 W2'
_chemical_oxdiff_usercomment     'red needles from toluene'
_reflns_odcompleteness_completeness 99.25
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 B1-H1 = B2-H2
 1.15 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C85 \\sim C86 \\sim C87 \\sim C88 \\sim C89 \\sim C90: within 1.7A with sigma
of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
C117 \\sim C122 \\sim C121 \\sim C120 \\sim C119 \\sim C118: within 1.7A with
sigma of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
C79 \\sim C84 \\sim C83 \\sim C82 \\sim C81 \\sim C80: within 1.7A with sigma
of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
C66 \\sim C71 \\sim C70 \\sim C69 \\sim C68 \\sim C67: within 1.7A with sigma
of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
C116 \\sim C110 \\sim C115 \\sim C114 \\sim C113 \\sim C112 \\sim C111: within
1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
C91 \\sim C96 \\sim C95 \\sim C94 \\sim C93 \\sim C92: within 1.7A with sigma
of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
C41 \\sim C46 \\sim C45 \\sim C44 \\sim C43 \\sim C42: within 1.7A with sigma
of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
C54 \\sim C55 \\sim C56 \\sim C57 \\sim C58 \\sim C59: within 1.7A with sigma
of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
C60 \\sim C61 \\sim C62 \\sim C63 \\sim C64 \\sim C65: within 1.7A with sigma
of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
C47 \\sim C48 \\sim C49 \\sim C50 \\sim C51 \\sim C52: within 1.7A with sigma
of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
C98 \\sim C99 \\sim C100 \\sim C101 \\sim C102 \\sim C103: within 1.7A with
sigma of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
C72 \\sim C73 \\sim C74 \\sim C75 \\sim C76 \\sim C77: within 1.7A with sigma
of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
C31 \\sim C32 \\sim C33 \\sim C34 \\sim C35: within 1.7A with sigma of 0.02 and
sigma for terminal atoms of 0.04 within 1.7A
C40 \\sim C39 \\sim C38 \\sim C37 \\sim C36: within 1.7A with sigma of 0.02 and
sigma for terminal atoms of 0.04 within 1.7A
Uanis(C2) = Uanis(C5)
Uanis(C1) = Uanis(C4)
Uanis(C3) = Uanis(C6)
Uanis(C53) = Uanis(C97) = Uanis(C78)
4. Rigid body (RIGU) restrains
 C85, C86, C87, C88, C89, C90
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C116, C110, C115, C114, C113, C112, C111
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C72, C77, C76, C75, C74, C73
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Ternary CH refined with riding coordinates and stretchable bonds:
 B1(H1), B2(H2)
5.b Secondary CH2 refined with riding coordinates:
 C53(H53A,H53B), C97(H97A,H97B), C78(H78A,H78B)
5.c Aromatic/amide H refined with riding coordinates:
 C48(H48), C105(H105), C108(H108), C109(H109), C106(H106), C103(H103),
 C33(H33), C49(H49), C42(H42), C100(H100), C28(H28), C107(H107), C13(H13),
 C55(H55), C99(H99), C51(H51), C67(H67), C65(H65), C92(H92), C52(H52), C76(H76),
  C23(H23), C44(H44), C94(H94), C70(H70), C46(H46), C71(H71), C18(H18),
 C50(H50), C93(H93), C73(H73), C96(H96), C43(H43), C59(H59), C101(H101),
 C74(H74), C45(H45), C102(H102), C57(H57), C77(H77), C56(H56), C63(H63),
 C95(H95), C84(H84), C61(H61), C64(H64), C38(H38), C80(H80), C86(H86), C62(H62),
  C83(H83), C122(H122), C68(H68), C75(H75), C58(H58), C69(H69), C115(H115),
 C113(H113), C87(H87), C89(H89), C90(H90), C112(H112), C82(H82), C88(H88),
 C118(H118), C121(H121), C81(H81), C120(H120), C114(H114), C119(H119),
 C111(H111)
5.d Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C26(H26A,H26B,H26C), C35(H35A,H35B,
 H35C), C15(H15A,H15B,H15C), C25(H25A,H25B,H25C), C20(H20A,H20B,H20C), C16(H16A,
 H16B,H16C), C21(H21A,H21B,H21C), C36(H36A,H36B,H36C), C40(H40A,H40B,H40C),
 C11(H11A,H11B,H11C), C116(H11D,H11E,H11F)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              49252
_shelx_fab_checksum              62993
_ins_header
;
TITL RAM-WC3Agdppm_scale3 in P2(1)/n 
REM P2(1)/n (#14 in standard setting)
CELL 1.54184  15.377016  30.635634  28.810686  90.0000  98.3095  90.0000
ZERR    8.00   0.000382   0.000701   0.001566   0.0000   0.0036   0.0000
LATT  1
SYMM -x+1/2, y+1/2,-z+1/2 
SFAC C H B N O P Ag W
UNIT 520.00 528.00 16.00 96.00 32.00 16.00 24.00 16.00
TREF
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.139
_oxdiff_exptl_absorpt_empirical_full_min 0.909