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_1554311
_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         'C15 H18 O2'
_chemical_formula_sum            'C15 H18 O2'
_chemical_formula_weight         230.29
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-03-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-04-12 deposited with the CCDC.
2018-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                111.795(7)
_cell_angle_beta                 99.480(6)
_cell_angle_gamma                90.087(7)
_cell_formula_units_Z            2
_cell_length_a                   5.6491(4)
_cell_length_b                   11.5037(11)
_cell_length_c                   11.5175(7)
_cell_measurement_reflns_used    2023
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.8390
_cell_measurement_theta_min      4.1880
_cell_volume                     683.87(10)
_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  'XH (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_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     56.00  82.00   1.00    1.00    --    0.00  57.00 120.00   26
  2  \w    -21.00  14.00   1.00    1.00    --    0.00 -19.00  90.00   35
  3  \w    -73.00 -31.00   1.00    1.00    --    0.00 -38.00  30.00   42
  4  \w    -17.00  12.00   1.00    1.00    --    0.00  57.00  30.00   29
  5  \w     11.00  37.00   1.00    1.00    --    0.00  57.00 120.00   26
  6  \w     21.00  85.00   1.00    1.00    --    0.00  57.00  30.00   64
  7  \w    -26.00  16.00   1.00    1.00    --    0.00 -38.00  30.00   42
  8  \w    -23.00   8.00   1.00    1.00    --    0.00  57.00 120.00   31
  9  \w      6.00  97.00   1.00    2.00    --   95.80 -61.00-180.00   91
 10  \w      7.00  51.00   1.00    2.00    --   95.80 -61.00 -60.00   44
 11  \w     39.00 106.00   1.00    2.00    --   95.80 -61.00  90.00   67
 12  \w     81.00 120.00   1.00    2.00    --   95.80 -61.00 -60.00   39
 13  \w     65.00 115.00   1.00    2.00    --   95.80 -82.00 120.00   50
 14  \w     17.00  51.00   1.00    2.00    --   95.80 -82.00-180.00   34
 15  \w     84.00 125.00   1.00    2.00    --   95.80 -77.00 -30.00   41
 16  \w     92.00 124.00   1.00    2.00    --   95.80 -82.00   0.00   32
 17  \w    139.00 185.00   1.00    2.00    --   95.80  30.00  30.00   46
 18  \w     38.00  71.00   1.00    2.00    --   95.80 -77.00 -30.00   33
 19  \w     78.00 118.00   1.00    2.00    --   95.80  30.00  30.00   40
 20  \w     65.00 127.00   1.00    2.00    --   95.80 -82.00-180.00   62
 21  \w     16.00  41.00   1.00    2.00    --   95.80 -82.00 -90.00   25
 22  \w     58.00 114.00   1.00    2.00    --   95.80 -82.00 -90.00   56
 23  \w      7.00  35.00   1.00    2.00    --   95.80 -77.00 -30.00   28
 24  \w     69.00 170.00   1.00    2.00    --   95.80  15.00  90.00  101
 25  \w      7.00  92.00   1.00    2.00    --   95.80 -45.00 -30.00   85
 26  \w     14.00  98.00   1.00    2.00    --   95.80 -30.00  60.00   84
;
_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      0.0098804000
_diffrn_orient_matrix_UB_12      0.1405046000
_diffrn_orient_matrix_UB_13      0.0216880000
_diffrn_orient_matrix_UB_21      -0.2742630000
_diffrn_orient_matrix_UB_22      -0.0001519000
_diffrn_orient_matrix_UB_23      -0.0052192000
_diffrn_orient_matrix_UB_31      0.0385369000
_diffrn_orient_matrix_UB_32      0.0340319000
_diffrn_orient_matrix_UB_33      0.1446839000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5976
_diffrn_reflns_theta_full        67.08
_diffrn_reflns_theta_max         67.08
_diffrn_reflns_theta_min         4.15
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.576
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86057
_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    1.118
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2405
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0680
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1400P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2031
_refine_ls_wR_factor_ref         0.2213
_reflns_number_gt                1683
_reflns_number_total             2405
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8qo00318a3.cif
_cod_data_source_block           exp_289
_cod_original_cell_volume        683.87(9)
_cod_database_code               1554311
_reflns_odcompleteness_completeness 99.47
_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, All O(H) groups
2. Rigid bond restraints
 C2, C3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C4(H4), C5(H5), C9(H9)
3.c X=CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
3.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 3.592
_oxdiff_exptl_absorpt_empirical_full_min 0.515