Catalytic Functionalization of C-H Bonds of Azulene by Carbene/Nitrene Incorporation.
Carreras, Javier; Popowski, Yanay; Caballero, Ana; Amir, Elizabeth; Pérez, Pedro J; The Journal of organic chemistry 83 (2018) 11125–11132; doi:10.1021/acs.joc.8b01731

data_4035649
_publ_section_title
;
 Catalytic Functionalization of C-H Bonds of Azulene by Carbene/Nitrene
 Incorporation.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11125
_journal_page_last               11132
_journal_paper_doi               10.1021/acs.joc.8b01731
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C26 H24 N2 O2'
_chemical_formula_sum            'C26 H24 N2 O2'
_chemical_formula_weight         396.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 91.242(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   38.954(3)
_cell_length_b                   5.8456(4)
_cell_length_c                   9.0416(6)
_cell_measurement_reflns_used    3792
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      24.981
_cell_measurement_theta_min      2.092
_cell_volume                     2058.4(3)
_computing_cell_refinement       'Saint, Bruker-AXS'
_computing_data_collection       'Apex2, Bruker-AXS'
_computing_data_reduction        'Saint, Bruker-AXS'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 1.75
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'ApexDuo, Bruker-AXS'
_diffrn_measurement_method       '0.5 deg. \f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            3792
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        24.981
_diffrn_reflns_theta_max         24.981
_diffrn_reflns_theta_min         2.092
_diffrn_source                   'ImuS micro-focus'
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, Bruker-AXS'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.071
_exptl_crystal_size_min          0.043
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.651
_refine_diff_density_rms         0.160
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.277
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1782
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.277
_refine_ls_R_factor_all          0.1239
_refine_ls_R_factor_gt           0.0781
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2234
_refine_ls_wR_factor_ref         0.3380
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1221
_reflns_number_total             1782
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01731_si_003.cif
_cod_data_source_block           yp2
_cod_original_cell_volume        2058.4(2)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4035649
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_min   0.975
_shelx_estimated_absorpt_t_max   0.997