2,3-Allenoic acids via palladium-catalyzed carboxylation of propargylic alcohols
Zheng, Wei-Feng; Zhang, Wanli; Huang, Jianhao; Yu, Yibo; Qian, Hui; Ma, Shengming; Organic Chemistry Frontiers 5 (2018) 1900–; doi:10.1039/C8QO00318A

data_1554310
_publ_section_title
;
 2,3-Allenoic acids via palladium-catalyzed carboxylation of propargylic
 alcohols
;
_journal_issue                   12
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1900
_journal_paper_doi               10.1039/C8QO00318A
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C17 H14 O2'
_chemical_formula_sum            'C17 H14 O2'
_chemical_formula_weight         250.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-12-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-02-01 deposited with the CCDC.
2018-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.468(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5915(2)
_cell_length_b                   15.1258(2)
_cell_length_c                   9.0257(2)
_cell_measurement_reflns_used    6890
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.7690
_cell_measurement_theta_min      4.4090
_cell_volume                     1363.29(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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     -4.00  21.00   1.00    1.00    --    0.00  57.00 -60.00   25
  2  \w    -62.00  -1.00   1.00    1.00    --    0.00 -38.00  60.00   61
  3  \w    -58.00  18.00   1.00    1.00    --    0.00 -38.00-180.00   76
  4  \w     29.00  89.00   1.00    1.00    --    0.00  57.00 -60.00   60
  5  \w     36.00  61.00   1.00    1.00    --    0.00  38.00  60.00   25
  6  \w    -83.00 -57.00   1.00    1.00    --    0.00 -38.00 -90.00   26
  7  \w    -17.00  28.00   1.00    1.00    --    0.00  38.00  60.00   45
  8  \w    -86.00 -60.00   1.00    1.00    --    0.00 -38.00-180.00   26
  9  \w    123.00 182.00   1.00    1.00    --   95.80  77.00-150.00   59
 10  \w     73.00  99.00   1.00    1.00    --   95.80 -82.00-150.00   26
 11  \w      7.00 128.00   1.00    1.00    --   95.80 -82.00 -90.00  121
 12  \w     65.00 117.00   1.00    1.00    --   95.80  77.00-150.00   52
 13  \w      6.00 115.00   1.00    1.00    --   95.80 -30.00 -30.00  109
 14  \w     10.00 101.00   1.00    1.00    --   95.80 -61.00 -90.00   91
 15  \w     69.00 126.00   1.00    1.00    --   95.80 -82.00 120.00   57
 16  \w     61.00 101.00   1.00    1.00    --   95.80 -82.00  60.00   40
 17  \w     29.00 112.00   1.00    1.00    --   95.80 -61.00  90.00   83
 18  \w     82.00 128.00   1.00    1.00    --   95.80 -82.00 -30.00   46
 19  \w    103.00 185.00   1.00    1.00    --   95.80  15.00-180.00   82
 20  \w      7.00  46.00   1.00    1.00    --   95.80 -82.00 -30.00   39
 21  \w     70.00  98.00   1.00    1.00    --   95.80  15.00-180.00   28
 22  \w     24.00  50.00   1.00    1.00    --   95.80 -82.00-150.00   26
 23  \w     25.00  50.00   1.00    1.00    --   95.80 -82.00  60.00   25
 24  \w      7.00  55.00   1.00    1.00    --   95.80 -77.00-120.00   48
 25  \w    118.00 144.00   1.00    1.00    --   95.80  30.00 -60.00   26
 26  \w     14.00 101.00   1.00    1.00    --   95.80 -30.00  60.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0590664000
_diffrn_orient_matrix_UB_12      -0.0717268000
_diffrn_orient_matrix_UB_13      -0.0789531000
_diffrn_orient_matrix_UB_21      -0.1351375000
_diffrn_orient_matrix_UB_22      -0.0490924000
_diffrn_orient_matrix_UB_23      -0.0516481000
_diffrn_orient_matrix_UB_31      -0.0452278000
_diffrn_orient_matrix_UB_32      0.0531005000
_diffrn_orient_matrix_UB_33      -0.1545044000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12937
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.072
_diffrn_reflns_theta_max         67.072
_diffrn_reflns_theta_min         4.428
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.629
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.0070(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2413
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0369
_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^)+(0.0510P)^2^+0.1740P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1021
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2174
_reflns_number_total             2413
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00318a2.cif
_cod_data_source_block           exp_160
_cod_database_code               1554310
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.843
_shelx_estimated_absorpt_t_min   0.761
_reflns_odcompleteness_completeness 99.96
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              1617
_shelx_hkl_checksum              99404
_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 2.007
_oxdiff_exptl_absorpt_empirical_full_min 0.453