Synthesis of 3-Azabicyclo[m.2.0] Ring Systems via Copper-Catalyzed Cascade Reaction of Diazo Compounds with 1,n-Allenynes.
He, Min; Chen, Nuan; Liu, Lala; Zhu, Yuqi; Li, Qing; Li, Hongguang; Lang, Ming; Wang, Jian; Peng, Shiyong; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00149

data_4037999
_publ_section_title
;
 Synthesis of 3-Azabicyclo[m.2.0] Ring Systems via Copper-Catalyzed
 Cascade Reaction of Diazo Compounds with 1,n-Allenynes.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00149
_journal_year                    2020
_chemical_formula_moiety         'C27 H29 N O4 S'
_chemical_formula_sum            'C27 H29 N O4 S'
_chemical_formula_weight         463.57
_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     dual
_audit_creation_date             2019-12-06
_audit_creation_method
;
Olex2 1.3-alpha
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                90
_cell_angle_beta                 114.996(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5776(19)
_cell_length_b                   11.6775(10)
_cell_length_c                   15.460(2)
_cell_measurement_reflns_used    2371
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      24.5080
_cell_measurement_theta_min      3.0560
_cell_volume                     2385.3(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -19.00  67.00   1.00    8.00    --   11.74  19.00-180.00   86
  2  \w    -63.00  36.00   1.00    8.00    --   11.74 -37.00 -30.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0047464000
_diffrn_orient_matrix_UB_12      0.0024135000
_diffrn_orient_matrix_UB_13      0.0436818000
_diffrn_orient_matrix_UB_21      0.0274690000
_diffrn_orient_matrix_UB_22      -0.0521201000
_diffrn_orient_matrix_UB_23      0.0148674000
_diffrn_orient_matrix_UB_31      0.0458424000
_diffrn_orient_matrix_UB_32      0.0313443000
_diffrn_orient_matrix_UB_33      0.0208007000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9704
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.270
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4202
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.1268
_refine_ls_R_factor_gt           0.0804
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0924P)^2^+2.3432P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1953
_refine_ls_wR_factor_ref         0.2267
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2622
_reflns_number_total             4202
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00149_si_004.cif
_cod_data_source_block           p415-2
_cod_database_code               4037999
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.978
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2. Restrained distances
 C1-C6
 1.45 with sigma of 0.02
3. Rigid bond restraints
 C1, C6
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C1 \\sim C6: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
5.a Ternary CH refined with riding coordinates:
 C12(H12), C14(H14)
5.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B), C16(H16A,H16B), C8(H8A,H8B)
5.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C26(H26), C13(H13), C25(H25), C22(H22), C23(H23), C6(H6), C2(H2),
 C5(H5), C3(H3), C4(H4)
5.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              61369
_shelx_hkl_checksum              64466
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.592
_oxdiff_exptl_absorpt_empirical_full_min 0.645