Palladium(II)-catalyzed aerobic oxidative O-H/C-H isocyanide insertion: facile access to pyrrolo[2,1-<i>c</i>][1,4]benzoxazine derivatives.
Luo, Liangliang; Chen, Xiao-Pan; Li, Zhao-Feng; Zhou, Yuan; Xiao, You-Cai; Chen, Fen-Er; Organic & biomolecular chemistry 19 (2021) 4364–4368; doi:10.1039/d1ob00393c

data_7158043
_publ_section_title
;
 Palladium(II)-catalyzed aerobic oxidative O-H/C-H isocyanide insertion:
 facile access to pyrrolo[2,1-<i>c</i>][1,4]benzoxazine derivatives.
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_journal_issue                   19
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4364
_journal_page_last               4368
_journal_paper_doi               10.1039/d1ob00393c
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         '0.5(C16 H18 N2 O2)'
_chemical_formula_sum            'C8 H9 N O'
_chemical_formula_weight         135.16
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-03-30 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.1570(10)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   22.5105(8)
_cell_length_b                   6.8064(2)
_cell_length_c                   20.6235(7)
_cell_measurement_reflns_used    4176
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      27.236
_cell_measurement_theta_min      2.220
_cell_volume                     2811.50(16)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0733
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21970
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.034
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0791 before and 0.0654 after correction.
The Ratio of minimum to maximum transmission is 0.9548.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       needle
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3496
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0555
_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^)+(0.0490P)^2^+4.1284P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1449
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2333
_reflns_number_total             3496
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00393c2.cif
_cod_data_source_block           mo_cfe_lll_1_120k_3_0m_a
_cod_depositor_comments          'Adding full bibliography for 7158043.cif.'
_cod_original_cell_volume        2811.49(16)
_cod_database_code               7158043
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.973
_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. Others
 Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=0.5*(1-FVAR(2))
 Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=0.5*FVAR(2)
 Fixed Sof: H00H(0.5) H00I(0.5) H00J(0.5) H01A(0.5) H01B(0.5) H01C(0.5)
 H01D(0.5) H01E(0.5) H01F(0.5)
3.a Riding coordinates:
 C00Y(H00D,H00E,H00F), C00Z(H00H,H00I,H00J), C010(H01A,H01B,H01C), C011(H01D,
 H01E,H01F), C2(H2A,H2B,H2C), C2A(H2AA,H2AB,H2AC)
3.b Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00K(H00K), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P),
 C00Q(H00Q), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00X(H00X)
3.c Idealised Me refined as rotating group:
 C00W(H00A,H00B,H00C)
;
_shelx_res_checksum              38955
_olex2_submission_special_instructions 'No special instructions were received'