Synthesis of Amides and Nitriles from Vinyl Azides and p-Quinone Methides.
Lin, Chen; Shen, Yangyong; Huang, Bo; Liu, Yu; Cui, Sunliang; The Journal of organic chemistry 82 (2017) 3950–3956; doi:10.1021/acs.joc.7b00145

data_4037473
_publ_section_title
;
 Synthesis of Amides and Nitriles from Vinyl Azides and p-Quinone
 Methides.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3950
_journal_page_last               3956
_journal_paper_doi               10.1021/acs.joc.7b00145
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C26 H35 N O4'
_chemical_formula_sum            'C26 H35 N O4'
_chemical_formula_weight         425.55
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-05-24
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.019(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.837(2)
_cell_length_b                   10.7069(16)
_cell_length_c                   16.375(3)
_cell_measurement_reflns_used    2838
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.025
_cell_measurement_theta_min      2.317
_cell_volume                     2444.1(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17050
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.537
_diffrn_reflns_theta_min         1.601
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0589 before and 0.0427 after correction.
The Ratio of minimum to maximum transmission is 0.8985.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         5616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0465
_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^)+(0.0571P)^2^+0.3151P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1380
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3245
_reflns_number_total             5616
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00145_si_003.cif
_cod_data_source_block           a
_cod_original_cell_volume        2444.2(6)
_cod_database_code               4037473
_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:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C6(H6), C5(H5)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C21(H21A,H21B,H21C), C25(H25A,H25B,H25C), C24(H24A,H24B,
 H24C), C22(H22A,H22B,H22C), C20(H20A,H20B,H20C), C2(H2A,H2B,H2C), C9(H9A,H9B,
 H9C), C1(H1A,H1B,H1C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'