Metathesis Reaction of Diazo Compounds and para-Quinone Methides for C-C Double Bond Formation: Synthesis of Tetrasubstituted Alkenes and Quinolinones.
Huang, Bo; Shen, Yangyong; Mao, Zhenjun; Liu, Yu; Cui, Sunliang; Organic letters 18 (2016) 4888–4891; doi:10.1021/acs.orglett.6b02365

data_1544166
_publ_section_title
;
 Metathesis Reaction of Diazo Compounds and para-Quinone Methides for C-C
 Double Bond Formation: Synthesis of Tetrasubstituted Alkenes and
 Quinolinones.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4888
_journal_page_last               4891
_journal_paper_doi               10.1021/acs.orglett.6b02365
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C32 H38 O3'
_chemical_formula_sum            'C32 H38 O3'
_chemical_formula_weight         470.62
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-03-24
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 114.89(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.361(2)
_cell_length_b                   25.338(3)
_cell_length_c                   11.4215(17)
_cell_measurement_reflns_used    914
_cell_measurement_temperature    170
_cell_measurement_theta_max      29.5081
_cell_measurement_theta_min      3.1055
_cell_volume                     2719.9(9)
_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
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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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0202726000
_diffrn_orient_matrix_UB_12      -0.0259384000
_diffrn_orient_matrix_UB_13      -0.0239831000
_diffrn_orient_matrix_UB_21      -0.0597597000
_diffrn_orient_matrix_UB_22      0.0102618000
_diffrn_orient_matrix_UB_23      -0.0531257000
_diffrn_orient_matrix_UB_31      0.0414080000
_diffrn_orient_matrix_UB_32      0.0021076000
_diffrn_orient_matrix_UB_33      -0.0359407000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0857
_diffrn_reflns_av_unetI/netI     0.1437
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10726
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.11
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97291
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4947
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1617
_refine_ls_R_factor_gt           0.0681
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0341P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1605
_reflns_number_gt                2374
_reflns_number_total             4947
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b02365_si_003.cif
_cod_data_source_block           160324_hb_1_24b
_cod_depositor_comments
'Adding full bibliography for 1544166--1544170.cif.'
_cod_original_cell_volume        2720.1(8)
_cod_database_code               1544166
_chemical_oxdiff_formula         'C10 h10 O2 n2'
_reflns_odcompleteness_completeness 99.28
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Restrained distances
 O1-H1
 0.86 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C5(H5), C20(H20), C21(H21), C23(H23), C24(H24), C27(H27), C28(H28),
 C30(H30), C31(H31)
3.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13B,H13A,
 H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C25(H25A,
 H25B,H25C), C32(H32A,H32B,H32C)
;