Ruthenium(II)-Catalyzed C-H Allenylation-Based Approach to Allenoic Acids
Wu, Xiaoyan; Fan, Junjie; Fu, Chunling; Ma, Shengming; Chemical Science  (2019) –; doi:10.1039/C9SC00603F

data_1551010
_publ_section_title
;
 Ruthenium(II)-Catalyzed C-H Allenylation-Based Approach to Allenoic Acids
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC00603F
_journal_year                    2019
_chemical_formula_moiety         'C16 H19 F O2'
_chemical_formula_sum            'C16 H19 F O2'
_chemical_formula_weight         262.31
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-11-05 deposited with the CCDC.    2019-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.778(15)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7724(13)
_cell_length_b                   15.7829(12)
_cell_length_c                   9.9065(12)
_cell_measurement_reflns_used    1330
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.1419
_cell_measurement_theta_min      3.3327
_cell_volume                     1503.7(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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      296.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   21.00   86.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   77.0000    0.0000 65

  2 omega  -15.00   90.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   77.0000  120.0000 105
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0687920000
_diffrn_orient_matrix_UB_12      -0.0162611000
_diffrn_orient_matrix_UB_13      0.0346548000
_diffrn_orient_matrix_UB_21      0.0017767000
_diffrn_orient_matrix_UB_22      0.0010684000
_diffrn_orient_matrix_UB_23      -0.0706899000
_diffrn_orient_matrix_UB_31      0.0266032000
_diffrn_orient_matrix_UB_32      0.0418647000
_diffrn_orient_matrix_UB_33      0.0152686000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5576
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         3.339
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2735
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0602
_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^)+(0.0793P)^2^+0.2197P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1483
_refine_ls_wR_factor_ref         0.1764
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1722
_reflns_number_total             2735
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc00603f2.cif
_cod_data_source_block           180621_wxy_2_132
_cod_database_code               1551010
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'c h n o'
_shelx_estimated_absorpt_t_max   0.968
_shelx_estimated_absorpt_t_min   0.963
_reflns_odcompleteness_completeness 99.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2. Restrained distances
 O2-H2
 0.86 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4)
3.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              53560
_olex2_submission_special_instructions 'No special instructions were received'