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_1544169
_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         'C31 H36 O3'
_chemical_formula_sum            'C31 H36 O3'
_chemical_formula_weight         456.60
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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                107.248(7)
_cell_angle_beta                 100.253(6)
_cell_angle_gamma                93.543(5)
_cell_formula_units_Z            2
_cell_length_a                   9.6348(6)
_cell_length_b                   11.1945(8)
_cell_length_c                   13.2323(11)
_cell_measurement_reflns_used    2051
_cell_measurement_temperature    170
_cell_measurement_theta_max      29.3680
_cell_measurement_theta_min      2.8887
_cell_volume                     1331.24(18)
_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      -0.0125185000
_diffrn_orient_matrix_UB_12      0.0279490000
_diffrn_orient_matrix_UB_13      -0.0418725000
_diffrn_orient_matrix_UB_21      -0.0121993000
_diffrn_orient_matrix_UB_22      -0.0606433000
_diffrn_orient_matrix_UB_23      -0.0391697000
_diffrn_orient_matrix_UB_31      -0.0733208000
_diffrn_orient_matrix_UB_32      -0.0030598000
_diffrn_orient_matrix_UB_33      0.0015221000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8475
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         2.89
_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  0.95524
_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    1.139
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           fullcycle
_refine_ls_number_parameters     330
_refine_ls_number_reflns         4841
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0537
_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^)+(0.0657P)^2^+0.1169P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1269
_refine_ls_wR_factor_ref         0.1515
_reflns_number_gt                3155
_reflns_number_total             4841
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b02365_si_004.cif
_cod_data_source_block           160323_hb_1_85a
_cod_depositor_comments
'Adding full bibliography for 1544166--1544170.cif.'
_cod_original_cell_volume        1331.23(17)
_cod_database_code               1544169
_chemical_oxdiff_formula         'C10 h10 O2 n2'
_reflns_odcompleteness_completeness 99.65
_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
 H1-O1
 0.84 with sigma of 0.02
3. Others
 Sof(H22)=Sof(C25A)=Sof(H25D)=Sof(H25E)=Sof(H25F)=1-FVAR(1)
 Sof(H29)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C5(H5), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C27(H27),
 C28(H28), C29(H29), C30(H30), C31(H31)
4.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C25(H25A,
 H25B,H25C), C25A(H25D,H25E,H25F)
;