A K-Arylacetylide Complex for Catalytic Terminal Alkyne Functionalization using KOtBu as a Precatalyst
Mandal, Swadhin K.; Ahmed, Jasimuddin; Swain, Asim Kumar; Das, Arpan; Govindarajan, R.; Bhunia, Mrinal; Chemical Communications  (2019) –; doi:10.1039/C9CC07833A

data_7124366
_publ_section_title
;
 A K-Arylacetylide Complex for Catalytic Terminal Alkyne Functionalization
 using KOtBu as a Precatalyst
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC07833A
_journal_year                    2019
_chemical_formula_moiety         'C16 H29 K N2 O6, C16 H28 K N2 O6'
_chemical_formula_sum            'C32 H57 K2 N4 O12'
_chemical_formula_weight         768.01
_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     dual
_audit_creation_date             2019-08-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-31 deposited with the CCDC.    2019-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.419(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.5229(14)
_cell_length_b                   8.6696(3)
_cell_length_c                   21.8344(19)
_cell_measurement_reflns_used    5685
_cell_measurement_temperature    99.73(16)
_cell_measurement_theta_max      66.0390
_cell_measurement_theta_min      3.3530
_cell_volume                     3927.5(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_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      99.73(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details
;
  1 omega  -12.00  102.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       26.0811   57.0000    0.0000 114

  2 omega   57.00  120.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       26.0811  178.0000  -60.0000 63

  3 omega  -12.00  102.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       26.0811   57.0000  120.0000 114

  4 omega  100.00  152.00   1.0000   20.0200
omega____ theta____ kappa____ phi______ frames
    -       67.0406  111.0000   90.0000 52

  5 omega  100.00  152.00   1.0000   20.0200
omega____ theta____ kappa____ phi______ frames
    -       67.0406  111.0000  150.0000 52

  6 omega  100.00  152.00   1.0000   20.0200
omega____ theta____ kappa____ phi______ frames
    -       67.0406  111.0000 -150.0000 52

  7 omega  100.00  152.00   1.0000   20.0200
omega____ theta____ kappa____ phi______ frames
    -       67.0406  111.0000  -60.0000 52

  8 omega  100.00  152.00   1.0000   20.0200
omega____ theta____ kappa____ phi______ frames
    -       67.0406  111.0000  120.0000 52

  9 omega  100.00  152.00   1.0000   20.0200
omega____ theta____ kappa____ phi______ frames
    -       67.0406  111.0000   60.0000 52

 10 omega  -10.00  151.00   1.0000   20.0200
omega____ theta____ kappa____ phi______ frames
    -       67.0406   30.0000   30.0000 161

 11 omega   30.00  144.00   1.0000   20.0200
omega____ theta____ kappa____ phi______ frames
    -       67.0406   61.0000 -120.0000 114

 12 omega   24.00  117.00   1.0000   25.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -115.0000    5.3708 93

 13 omega   66.00  178.00   1.0000   25.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   74.0000   24.1077 112

 14 omega  101.00  178.00   1.0000   25.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000  150.0000 77

 15 omega   36.00  168.00   1.0000   25.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   32.0000   90.0000 132

 16 omega   61.00  109.00   1.0000   25.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000 -150.0000 48

 17 omega  100.00  168.00   1.0000   25.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   88.0000   58.0000 68

 18 omega   66.00  141.00   1.0000   25.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 75

 19 omega   73.00  115.00   1.0000   25.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   87.7281 42

 20 omega  128.00  154.00   1.0000   25.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -82.0000  -46.5702 26

 21 omega   23.00   72.00   1.0000   25.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   87.7281 49

 22 omega   74.00  101.00   1.0000   25.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000  -90.0000 27

 23 omega   86.00  130.00   1.0000   25.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  138.0000   90.0000 44

 24 omega   22.00  105.00   1.0000   25.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -82.0000  -46.5702 83

 25 omega   27.00   58.00   1.0000   25.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -104.0000  -90.0000 31

 26 omega  123.00  150.00   1.0000   25.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  104.0000   90.0000 27

 27 omega  103.00  138.00   1.0000   25.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  138.0000  120.0000 35

 28 omega  105.00  132.00   1.0000   25.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   54.0000 -120.0000 27

 29 omega  110.00  143.00   1.0000   25.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   65.0000   90.0000 33

 30 omega  152.00  178.00   1.0000   25.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   71.0000  -16.5183 26

 31 omega   72.00  168.00   1.0000   25.0200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   65.0000  150.0000 96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0519098000
_diffrn_orient_matrix_UB_12      0.0764140000
_diffrn_orient_matrix_UB_13      -0.0539063000
_diffrn_orient_matrix_UB_21      -0.0447997000
_diffrn_orient_matrix_UB_22      0.0128215000
_diffrn_orient_matrix_UB_23      0.0442684000
_diffrn_orient_matrix_UB_31      0.0284312000
_diffrn_orient_matrix_UB_32      0.1599733000
_diffrn_orient_matrix_UB_33      0.0221777000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21146
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        66.228
_diffrn_reflns_theta_max         66.228
_diffrn_reflns_theta_min         3.365
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.653
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       block
_exptl_crystal_F_000             1644
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.137
_refine_diff_density_min         -1.160
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.267
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         6507
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.267
_refine_ls_R_factor_all          0.1169
_refine_ls_R_factor_gt           0.0993
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2896
_refine_ls_wR_factor_ref         0.3165
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5139
_reflns_number_total             6507
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07833a2.cif
_cod_data_source_block           jasi_30_07
_cod_database_code               7124366
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C H N O K'
_reflns_odcompleteness_completeness 93.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.9269(15)
 0.0731(15)
2. 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
3.a Ternary CH refined with riding coordinates:
 C29(H29)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B),
 C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B),
  C15(H15A,H15B), C16(H16A,H16B), C18(H18A,H18B), C21(H21A,H21B), C22(H22A,
 H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B),
 C27(H27A,H27B), C28(H28A,H28B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B)
3.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C20(H20A,H20B,H20C)
;
_shelx_res_checksum              48380
_olex2_date_sample_data_collection 2019-07-30
_olex2_submission_special_instructions 'No special instructions were received'