Oxidative coupling of tetraalkynyltin with aldehydes leading to alkynyl ketones
Levashov, Andrey; Aksenov, Nicolai A.; Aksenova, Inna V.; Konshin, Valeriy V.; New J. Chem. 41 (2017) 8297–8304; doi:10.1039/C7NJ01376K

data_7056387
_publ_section_title
;
 Oxidative coupling of tetraalkynyltin with aldehydes leading to alkynyl
 ketones
;
_journal_issue                   16
_journal_name_full               'New J. Chem.'
_journal_page_first              8297
_journal_page_last               8304
_journal_paper_doi               10.1039/C7NJ01376K
_journal_volume                  41
_journal_year                    2017
_chemical_formula_moiety         'C26 H22 O3'
_chemical_formula_sum            'C26 H22 O3'
_chemical_formula_weight         382.43
_chemical_melting_point          414.2(2)
_chemical_name_common
'4-(3-phenylprop-2-ynoyl)phenyl 4-tert-butylbenzoate (4aj)'
_chemical_name_systematic        '4-(3-phenylpropioloyl)phenyl benzoate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-02
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2017-04-12 deposited with the CCDC.
2017-06-30 downloaded from the CCDC.
;
_cell_angle_alpha                88.139(2)
_cell_angle_beta                 87.315(2)
_cell_angle_gamma                80.902(3)
_cell_formula_units_Z            2
_cell_length_a                   6.7125(3)
_cell_length_b                   9.9947(3)
_cell_length_c                   15.6535(3)
_cell_measurement_reflns_used    10012
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.3750
_cell_measurement_theta_min      4.3750
_cell_volume                     1035.50(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.9824
_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    -96.00  -2.00   1.00    1.33    --  -41.35 125.00   0.00   94
  2  \w   -113.00 -13.00   1.00    1.33    --  -41.35 -57.00 150.00  100
  3  \w    -66.00  33.00   1.00    1.33    --  -41.35  38.00  90.00   99
  4  \w    -69.00  32.00   1.00    1.33    --  -41.35  57.00 -60.00  101
  5  \w     81.00 178.00   1.00    5.30    --  106.96  45.00   0.00   97
  6  \w     34.00 121.00   1.00    5.30    --  106.96-125.00 120.00   87
  7  \w     74.00 178.00   1.00    5.30    --  106.96  77.00-120.00  104
  8  \w     25.00 109.00   1.00    5.30    --  106.96 -95.00-120.00   84
  9  \w     31.00 135.00   1.00    5.30    --  106.96 -30.00-180.00  104
 10  \w     94.00 178.00   1.00    5.30    --  106.96 125.00 -90.00   84
 11  \w     94.00 178.00   1.00    5.30    --  106.96 125.00-120.00   84
 12  \w     94.00 178.00   1.00    5.30    --  106.96 125.00 150.00   84
 13  \w     81.00 178.00   1.00    5.30    --  106.96  45.00-150.00   97
 14  \w     25.00 109.00   1.00    5.30    --  106.96 -95.00 -60.00   84
 15  \w     94.00 178.00   1.00    5.30    --  106.96 125.00 -60.00   84
 16  \w     35.00 136.00   1.00    5.30    --  106.96 -61.00 -90.00  101
 17  \w   -113.00 -13.00   1.00    1.33    --  -41.35 -57.00-120.00  100
 18  \w   -117.00  -9.00   1.00    1.33    --  -41.35 -77.00 -30.00  108
 19  \w   -117.00  -9.00   1.00    1.33    --  -41.35 -77.00  60.00  108
 20  \w     -3.00  80.00   1.00    1.33    --   41.35 -95.00 169.00   83
 21  \w     74.00 178.00   1.00    5.30    --  106.96  77.00  60.00  104
 22  \w     74.00 178.00   1.00    5.30    --  106.96  77.00  30.00  104
 23  \w     78.00 178.00   1.00    5.30    --  106.96  61.00 -60.00  100
 24  \w     74.00 178.00   1.00    5.30    --  106.96  77.00-150.00  104
 25  \w     79.00 178.00   1.00    5.30    --  106.96  30.00 120.00   99
 26  \w     74.00 178.00   1.00    5.30    --  106.96  77.00   0.00  104
 27  \w     78.00 178.00   1.00    5.30    --  106.96  61.00 120.00  100
 28  \w     78.00 178.00   1.00    5.30    --  106.96  61.00 150.00  100
 29  \w   -117.00  -9.00   1.00    1.33    --  -41.35 -77.00 150.00  108
 30  \w   -117.00  -9.00   1.00    1.33    --  -41.35 -77.00-150.00  108
 31  \w   -121.00   0.00   1.00    1.33    --  -41.35 -19.00 -90.00  121
 32  \w     17.00 116.00   1.00    1.33    --   41.35  38.00 -90.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1605568000
_diffrn_orient_matrix_UB_12      0.0093898000
_diffrn_orient_matrix_UB_13      0.0657951000
_diffrn_orient_matrix_UB_21      -0.1670832000
_diffrn_orient_matrix_UB_22      0.0608256000
_diffrn_orient_matrix_UB_23      0.0647713000
_diffrn_orient_matrix_UB_31      -0.0206056000
_diffrn_orient_matrix_UB_32      -0.1435119000
_diffrn_orient_matrix_UB_33      0.0344835000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19353
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.841
_diffrn_reflns_theta_min         4.482
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.630
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       prism
_exptl_crystal_F_000             404
_exptl_crystal_recrystallization_method 'recrystallized from EtOH'
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.227
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0535P)^2^+0.2550P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1038
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3728
_reflns_number_total             4133
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7nj01376k2.cif
_cod_data_source_block           anna331_01032017_al063_2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '414.0 - 414.4 K' was changed to
'414.2(2)' - the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7056387
_chemical_oxdiff_formula         C26H22O3
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C19(H19), C21(H21), C22(H22), C18(H18), C15(H15), C14(H14), C11(H11), C5(H5),
 C1(H1), C12(H12), C2(H2), C4(H4), C3(H3)
2.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2017-03-02
_olex2_exptl_crystal_mounting_method
'mounted by acrylic glue on the glass stick'
_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 2.376
_oxdiff_exptl_absorpt_empirical_full_min 0.596
_shelx_res_checksum              55249