Yttrium-Catalyzed Tandem Intermolecular Hydroalkoxylation/Claisen Rearrangement.
Zhou, Bo; Li, Long; Liu, Xin; Tan, Tong-De; Liu, Jinxian; Ye, Long-Wu; The Journal of organic chemistry 82 (2017) 10149–10157; doi:10.1021/acs.joc.7b01612

data_4032840
_publ_section_title
;
 Yttrium-Catalyzed Tandem Intermolecular Hydroalkoxylation/Claisen
 Rearrangement.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10149
_journal_page_last               10157
_journal_paper_doi               10.1021/acs.joc.7b01612
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C18 H16 O2'
_chemical_formula_sum            'C18 H16 O2'
_chemical_formula_weight         264.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.907(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0234(3)
_cell_length_b                   26.3300(9)
_cell_length_c                   7.4708(3)
_cell_measurement_reflns_used    3188
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      58.9380
_cell_measurement_theta_min      6.7190
_cell_volume                     1381.37(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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_temperature      173.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1903
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.832
_diffrn_measured_fraction_theta_max 0.998
_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    -98.00  -3.00   1.00   20.00    --  -30.00 -77.00-180.00   95
  2  \w   -103.00 -53.00   1.00   20.00    --  -30.00 178.00-120.00   50
  3  \w     20.00 104.00   1.00   20.00    --   37.00  57.00-120.00   84
  4  \w     35.00 109.00   1.00   20.00    --   37.00 178.00 120.00   74
  5  \w     17.00  84.00   1.00   20.00    --   86.50 -95.00 120.00   67
  6  \w     79.00 156.00   1.00   20.00    --   86.50 112.00 -30.00   77
  7  \w     18.00 104.00   1.00   20.00    --   86.50 -45.00  90.00   86
  8  \w     69.00 139.00   1.00   20.00    --   86.50  45.00 -90.00   70
  9  \w     17.00  48.00   1.00   20.00    --   86.50-112.00 120.00   31
 10  \w     25.00  51.00   1.00   20.00    --   86.50 -95.00-120.00   26
 11  \w     59.00  84.00   1.00   20.00    --   86.50 -95.00-120.00   25
 12  \w     71.00 143.00   1.00   20.00    --   86.50  61.00 -90.00   72
 13  \w     33.00  59.00   1.00   20.00    --   86.50 -95.00 -60.00   26
 14  \w     57.00  82.00   1.00   20.00    --   86.50 -95.00 -30.00   25
 15  \w     70.00  96.00   1.00   20.00    --   86.50 -63.00  12.47   26
 16  \w     78.00 109.00   1.00   20.00    --   86.50  61.00-120.00   31
 17  \w     38.00  75.00   1.00   25.00    --   86.50 -95.00  30.00   37
 18  \w     90.00 131.00   1.00   25.00    --   86.50 112.00   0.00   41
 19  \w     49.00  75.00   1.00   25.00    --   86.50  15.00-180.00   26
 20  \w     83.00 109.00   1.00   25.00    --   86.50  15.00-180.00   26
 21  \w     56.00  94.00   1.00   25.00    --   86.50 -61.00   0.00   38
 22  \w     89.00 114.00   1.00   25.00    --   86.50 112.00 -90.00   25
 23  \w     49.00 108.00   1.00   25.00    --   86.50  15.00  30.00   59
 24  \w   -103.00 -53.00   1.00   25.00    --  -30.00 178.00 150.00   50
 25  \w   -102.00 -57.00   1.00   25.00    --  -30.00-178.00  60.00   45
 26  \w     10.00 105.00   1.00   25.00    --   37.00  77.00  60.00   95
 27  \w     10.00 105.00   1.00   25.00    --   37.00  77.00 120.00   95
 28  \w     10.00 105.00   1.00   25.00    --   37.00  77.00 -30.00   95
 29  \w     60.00  98.00   1.00   25.00    --   86.50  77.00  60.00   38
 30  \w     68.00 153.00   1.00   25.00    --   86.50  61.00-180.00   85
 31  \w     10.00 105.00   1.00   25.00    --   37.00  77.00 -90.00   95
 32  \w     20.00  75.00   1.00   25.00    --   37.00  57.00  60.00   55
 33  \w     35.00 109.00   1.00   25.00    --   37.00 178.00  30.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0801008000
_diffrn_orient_matrix_UB_12      0.0175784000
_diffrn_orient_matrix_UB_13      0.1828809000
_diffrn_orient_matrix_UB_21      -0.1732531000
_diffrn_orient_matrix_UB_22      -0.0234765000
_diffrn_orient_matrix_UB_23      0.0931480000
_diffrn_orient_matrix_UB_31      0.1081407000
_diffrn_orient_matrix_UB_32      -0.0506277000
_diffrn_orient_matrix_UB_33      0.0202619000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_Laue_measured_fraction_full 0.832
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11391
_diffrn_reflns_point_group_measured_fraction_full 0.736
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         60.468
_diffrn_reflns_theta_min         3.357
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
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    1.271
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.118
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 1149 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         3671
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0435
_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^)+(0.0405P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.1007
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_full    0.635
_reflns_Friedel_fraction_max     0.764
_reflns_number_gt                3187
_reflns_number_total             3671
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01612_si_002.cif
_cod_data_source_block           zb20170619-2
_cod_depositor_comments          'Adding full bibliography for 4032840.cif.'
_cod_database_code               4032840
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 97.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C28(H28), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C35(H35A,H35B), C9(H9A,H9B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C23(H23), C19(H19), C7(H7), C1(H1), C3(H3), C5(H5), C20(H20), C2(H2),
 C25(H25), C22(H22), C16(H16), C30(H30), C21(H21), C12(H12), C4(H4), C32(H32),
 C34(H34), C33(H33), C13(H13), C15(H15), C31(H31), C14(H14)
;
_shelx_res_checksum              25967
_shelx_hkl_checksum              39757
_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 3.415
_oxdiff_exptl_absorpt_empirical_full_min 0.546