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_4120621
_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         'C24 H22 O3'
_chemical_formula_sum            'C24 H22 O3'
_chemical_formula_weight         358.41
_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     iterative
_audit_creation_date             2013-11-18
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.936(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7148(6)
_cell_length_b                   10.3476(6)
_cell_length_c                   17.2186(12)
_cell_measurement_reflns_used    2640
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      28.2740
_cell_measurement_theta_min      3.8440
_cell_volume                     1890.8(2)
_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      180.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9884
_diffrn_measured_fraction_theta_max 0.8333
_diffrn_measurement_details
;
  1 omega  -20.00   42.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579  -99.0000  150.0000 62

  2 omega  -16.00   81.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579   77.0000  -60.0000 97
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0439459000
_diffrn_orient_matrix_UB_12      0.0314115000
_diffrn_orient_matrix_UB_13      0.0208980000
_diffrn_orient_matrix_UB_21      0.0172592000
_diffrn_orient_matrix_UB_22      0.0605369000
_diffrn_orient_matrix_UB_23      -0.0146301000
_diffrn_orient_matrix_UB_31      -0.0473445000
_diffrn_orient_matrix_UB_32      -0.0070424000
_diffrn_orient_matrix_UB_33      -0.0328158000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7016
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         3.096
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81114
_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    1.259
_exptl_crystal_description
;
;
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3706
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0441P)^2^+0.2532P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1211
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2756
_reflns_number_total             3706
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja500118w_si_001.cif
_cod_data_source_block           exp_2494
_cod_database_code               4120621
_chemical_oxdiff_formula         'C1 H1 O1'
_reflns_odcompleteness_completeness 98.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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 Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.984
_shelxl_version_number           2013-3