From alkynes to spiroindole δ-lactams via a copper-nitrenoid intermediate featuring unusual 1,1-addition and high Z-selectivity
Ren, Zhiqiang; Feng, Tianhui; Li, Yeyao; Chu, Mengyi; Zheng, Ye; Gao, Tianli; Han, Bo; Guo, Ruili; Ma, Haojie; Wang, Ji-Jiang; Zhang, Yuqi; Chemical Science  (2026) –; doi:10.1039/D5SC09742H

data_1577003
_publ_section_title
;
 From alkynes to spiroindole &#x3b4;-lactams <i>via</i> a copper-nitrenoid
 intermediate featuring unusual 1,1-addition and high
 <i>Z</i>-selectivity.
;
_journal_issue                   19
_journal_name_full               'Chemical science'
_journal_page_first              9695
_journal_page_last               9702
_journal_paper_doi               10.1039/d5sc09742h
_journal_volume                  17
_journal_year                    2026
_chemical_formula_moiety         'C15 H14 N2 O3'
_chemical_formula_sum            'C15 H14 N2 O3'
_chemical_formula_weight         270.28
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-07-27
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-08-11 deposited with the CCDC.	2026-03-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.700(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5758(9)
_cell_length_b                   19.7461(17)
_cell_length_c                   6.5522(7)
_cell_measurement_reflns_used    3970
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      63.706
_cell_measurement_theta_min      6.269
_cell_volume                     1303.5(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      173.00
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            6986
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        63.915
_diffrn_reflns_theta_max         63.915
_diffrn_reflns_theta_min         6.276
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.803
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.5904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0714 before and 0.0453 after correction.
The Ratio of minimum to maximum transmission is 0.7847.
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    1.377
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2093
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.203
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0829
_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^)+(0.0922P)^2^+2.0170P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2044
_refine_ls_wR_factor_ref         0.2185
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1753
_reflns_number_total             2093
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc09742h3.cif
_cod_data_source_block           b_a
_cod_depositor_comments
'Adding full bibliography for 1577000--1577003.cif.'
_cod_database_code               1577003
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.889
_shelx_estimated_absorpt_t_min   0.856
_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. Uiso/Uaniso restraints and constraints
C5 \\sim C6 \\sim N2 \\sim C7 \\sim C12 \\sim C11 \\sim C10 \\sim C9 \\sim C8:
within 2A with sigma of 0.002 and sigma for terminal atoms of 0.004 within 2A
Uanis(C10) \\sim Ueq, Uanis(C9) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C11(H11), C6(H6), C8(H8), C10(H10)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              52039
_olex2_submission_special_instructions 'No special instructions were received'