Catalytic Arylboration of Spirocyclic Cyclobutenes: Rapid Access to Highly Substituted Spiro[3.n]alkanes
Simlandy, Amit Kumar; Lyu, Mao-Yun; Brown, M. Kevin; ACS Catalysis 11 (2021) 12815–12820; doi:10.1021/acscatal.1c03491

data_4519098
_publ_section_title
;
 Catalytic Arylboration of Spirocyclic Cyclobutenes: Rapid Access to
 Highly Substituted Spiro[3.n]alkanes
;
_journal_issue                   20
_journal_name_full               'ACS Catalysis'
_journal_page_first              12815
_journal_page_last               12820
_journal_paper_doi               10.1021/acscatal.1c03491
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C32 H35 N O4'
_chemical_formula_sum            'C32 H35 N O4'
_chemical_formula_weight         497.61
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-05-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                86.546(10)
_cell_angle_beta                 79.404(7)
_cell_angle_gamma                67.694(10)
_cell_formula_units_Z            4
_cell_length_a                   10.956(5)
_cell_length_b                   11.975(5)
_cell_length_c                   22.501(9)
_cell_measurement_reflns_used    9470
_cell_measurement_temperature    153.0
_cell_measurement_theta_max      26.83
_cell_measurement_theta_min      2.23
_cell_volume                     2684(2)
_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  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      153.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker VENTURE D8'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            135959
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.397
_diffrn_reflns_theta_min         1.838
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       plate
_exptl_crystal_F_000             1064
_exptl_crystal_preparation       synthetized
_exptl_crystal_recrystallization_method 'vapor diffusion of hexane into EtOAc'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     673
_refine_ls_number_reflns         10950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0463
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0488P)^2^+1.1112P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1215
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8279
_reflns_number_total             10950
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c03491_si_003.cif
_cod_data_source_block           mo_21122_0m_a
_cod_original_cell_volume        2684.6(19)
_cod_database_code               4519098
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.986
_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.a Ternary CH refined with riding coordinates:
 C13(H13), C12A(H12A), C12(H12), C13A(H13A)
2.b Secondary CH2 refined with riding coordinates:
 C7A(H7AA,H7AB), C6A(H6AA,H6AB), C9A(H9AA,H9AB), C10A(H10A,H10B), C10(H10C,
 H10D), C11A(H11A,H11B), C11(H11C,H11D), C9(H9A,H9B), C7(H7A,H7B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C25(H25), C15A(H15A), C23(H23), C17A(H17A), C22(H22), C26A(H26A), C19A(H19A),
 C26(H26), C31A(H31A), C16A(H16A), C18A(H18A), C25A(H25A), C32(H32), C29A(H29A),
  C22A(H22A), C31(H31), C23A(H23A), C28A(H28A), C32A(H32A), C30(H30),
 C30A(H30A), C28(H28), C15(H15), C16(H16), C29(H29), C17(H17), C19(H19),
 C18(H18)
2.d Idealised Me refined as rotating group:
 C3A(H3AA,H3AB,H3AC), C1(H1A,H1B,H1C), C1A(H1AA,H1AB,H1AC), C3(H3A,H3B,H3C),
 C2(H2A,H2B,H2C), C2A(H2AA,H2AB,H2AC)
;
_shelx_res_checksum              87480
_shelx_hkl_checksum              75920
_olex2_submission_original_sample_id AKS-IV-118
_olex2_submission_special_instructions 'No special instructions were received'