Formal Carbene Insertion into C-C Bond: Rh(I)-Catalyzed Reaction of Benzocyclobutenols with Diazoesters.
Xia, Ying; Liu, Zhenxing; Liu, Zhen; Ge, Rui; Ye, Fei; Hossain, Mohammad; Zhang, Yan; Wang, Jianbo; Journal of the American Chemical Society 136 (2014) 3013–; doi:10.1021/ja500118w

data_4120622
_publ_section_title
;
 Formal Carbene Insertion into C-C Bond: Rh(I)-Catalyzed Reaction of
 Benzocyclobutenols with Diazoesters.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3013
_journal_paper_doi               10.1021/ja500118w
_journal_volume                  136
_journal_year                    2014
_chemical_formula_moiety         'C21 H22 O3'
_chemical_formula_sum            'C21 H22 O3'
_chemical_formula_weight         322.38
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-12-12
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.804(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7262(5)
_cell_length_b                   10.4463(4)
_cell_length_c                   14.7106(7)
_cell_measurement_reflns_used    3014
_cell_measurement_temperature    289.94(10)
_cell_measurement_theta_max      63.1470
_cell_measurement_theta_min      4.2220
_cell_volume                     1725.04(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      289.94(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9209
_diffrn_measured_fraction_theta_max 0.9970
_diffrn_measurement_details
;
  1 omega -120.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.4282   19.0000    0.0000 182

  2 omega   89.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.4282  178.0000 -180.0000 36

  3 omega   60.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.4282  178.0000 -180.0000 26

  4 omega  147.00  174.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       94.5000  111.0000   90.0000 27

  5 omega  102.00  128.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       94.5000  178.0000   30.0000 26

  6 omega    2.00   37.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -25.0000 -120.0000 35

  7 omega   69.00  151.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       94.5000  178.0000 -120.0000 82

  8 omega   58.00   95.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       94.5000  178.0000  150.0000 37

  9 omega    0.00   30.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -25.0000   90.0000 30

 10 omega   89.00  115.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       94.5000  178.0000   90.0000 26

 11 omega   -2.00   24.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -91.0000 -120.0000 26

 12 omega   59.00   84.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -91.0000 -120.0000 25

 13 omega  113.00  143.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -91.0000 -120.0000 30

 14 omega    5.00   31.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -37.0000    0.0000 26

 15 omega    6.00   89.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -37.0000  150.0000 83

 16 omega   59.00   90.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -37.0000    0.0000 31

 17 omega   59.00   93.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -25.0000  150.0000 34

 18 omega  116.00  151.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       94.5000  178.0000  150.0000 35

 19 omega  118.00  165.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       94.5000  111.0000   60.0000 47

 20 omega   64.00   92.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       94.5000  -37.0000 -120.0000 28

 21 omega   55.00   80.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       94.5000   50.0000 -180.0000 25

 22 omega  118.00  173.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       94.5000   50.0000 -180.0000 55

 23 omega  103.00  131.00   1.0000    1.0400
omega____ theta____ kappa____ phi______ frames
    -       94.5000  111.0000   90.0000 28
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0565007000
_diffrn_orient_matrix_UB_12      0.0701722000
_diffrn_orient_matrix_UB_13      0.0944371000
_diffrn_orient_matrix_UB_21      0.1060383000
_diffrn_orient_matrix_UB_22      0.0399215000
_diffrn_orient_matrix_UB_23      -0.0357379000
_diffrn_orient_matrix_UB_31      -0.0664087000
_diffrn_orient_matrix_UB_32      0.1233208000
_diffrn_orient_matrix_UB_33      -0.0421754000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.895
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7109
_diffrn_reflns_point_group_measured_fraction_full 0.895
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         63.269
_diffrn_reflns_theta_min         3.938
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.653
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86395
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description
;
;
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0085(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2803
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0395
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0610P)^2^+0.2868P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1145
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2383
_reflns_number_total             2803
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja500118w_si_003.cif
_cod_data_source_block           exp_2532
_cod_original_cell_volume        1725.03(13)
_cod_database_code               4120622
_chemical_oxdiff_formula         'C1 H1 O1'
_chemical_oxdiff_usercomment     xy-13-122
_reflns_odcompleteness_completeness 92.09
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.881
_shelxl_version_number           2013-3