One-step construction of molecular complexity by tert-butyl nitrite (TBN)-initiated cascade α,β-sp<sup>3</sup> C-H bond difunctionalization and C-N bond cleavage.
He, Kaixuan; Li, Pengfei; Zhang, Shuwei; Chen, Qian; Ji, Honghe; Yuan, Yu; Jia, Xiaodong; Chemical communications (Cambridge, England) 54 (2018) 13232–13235; doi:10.1039/c8cc06946h

data_7122518
_publ_section_title
;
 One-step construction of molecular complexity by tert-butyl nitrite
 (TBN)-initiated cascade \a,\b-sp<sup>3</sup> C-H bond difunctionalization
 and C-N bond cleavage.
;
_journal_issue                   94
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              13232
_journal_page_last               13235
_journal_paper_doi               10.1039/c8cc06946h
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         '0.17(C11 H13 N3 O3)'
_chemical_formula_sum            'C1.91 H2.26 N0.52 O0.52'
_chemical_formula_weight         40.91
_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     direct
_audit_creation_date             2018-03-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-07-16 deposited with the CCDC.
2018-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.653(6)
_cell_angle_gamma                90
_cell_formula_units_Z            23
_cell_length_a                   5.8179(10)
_cell_length_b                   11.3981(19)
_cell_length_c                   17.623(3)
_cell_measurement_reflns_used    3814
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.29
_cell_measurement_theta_min      2.31
_cell_volume                     1167.4(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_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  0.0398
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11689
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_min         2.314
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6673
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1506 before and 0.0549 after correction.
The Ratio of minimum to maximum transmission is 0.8950.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             496
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2672
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0495
_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^)+(0.0552P)^2^+0.2120P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1269
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1727
_reflns_number_total             2672
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc06946h2.cif
_cod_data_source_block           danxie
_cod_depositor_comments          'Adding full bibliography for 7122518.cif.'
_cod_database_code               7122518
_shelx_shelxl_version_number     2014/7
_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:
 C12(H12A,H12B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C11(H11), C13(H13), C16(H16)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_shelx_res_checksum              5002
_olex2_submission_special_instructions 'No special instructions were received'