Copper-catalyzed remote double functionalization of allenynes.
Song, Yulong; Fu, Chunling; Zheng, Jian; Ma, Shengming; Chemical science 15 (2024) 7789–7794; doi:10.1039/d4sc00034j

data_1571480
_publ_section_title
;
 Copper-catalyzed remote double functionalization of allenynes.
;
_journal_issue                   20
_journal_name_full               'Chemical science'
_journal_page_first              7789
_journal_page_last               7794
_journal_paper_doi               10.1039/d4sc00034j
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C29 H36 B N O5'
_chemical_formula_sum            'C29 H36 B N O5'
_chemical_formula_weight         489.40
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-02-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-11-01 deposited with the CCDC.	2024-04-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.946(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.1404(17)
_cell_length_b                   28.846(3)
_cell_length_c                   11.2819(10)
_cell_measurement_reflns_used    9989
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      24.45
_cell_measurement_theta_min      2.31
_cell_volume                     5494.3(9)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_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      170.0
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0512
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            9613
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.010
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         1.857
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1720 before and 0.0764 after correction.
The Ratio of minimum to maximum transmission is 0.8942.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_description       block
_exptl_crystal_F_000             2096
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.552
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     716
_refine_ls_number_reflns         9613
_refine_ls_number_restraints     129
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1079
_refine_ls_R_factor_gt           0.0809
_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^)+(0.1799P)^2^+2.8220P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2435
_refine_ls_wR_factor_ref         0.2754
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6983
_reflns_number_total             9613
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc00034j2.cif
_cod_data_source_block           mo_210128_syl_8_41_0ma_tw
_cod_depositor_comments
'Adding full bibliography for 1571479--1571480.cif.'
_cod_database_code               1571480
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.986
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.791(3)
 0.209(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C56-C57 \\sim C56-C57A
 with sigma of 0.02
 C57-C58 \\sim C57A-C58A
 with sigma of 0.02
 C56-C58 \\sim C56-C58A
 with sigma of 0.04
4. Uiso/Uaniso restraints and constraints
O4 \\sim O5 \\sim C19 \\sim C20 \\sim B1 \\sim C21 \\sim C22 \\sim C23 \\sim
C24 \\sim C21A \\sim C22A \\sim C23A \\sim C24A: within 1.7A with sigma of 0.02
and sigma for terminal atoms of 0.04
C55 \\sim C56 \\sim C57 \\sim C58: within 1.7A with sigma of 0.02 and sigma for
terminal atoms of 0.04
C56 \\sim C57A \\sim C58A \\sim C57 \\sim C58: within 1.7A with sigma of 0.02
and sigma for terminal atoms of 0.04
Uanis(C22) = Uanis(C22A)
5. Others
 Sof(C23A)=Sof(H23D)=Sof(H23E)=Sof(H23F)=Sof(C24A)=Sof(H24D)=Sof(H24E)=
 Sof(H24F)=1-FVAR(1)
 Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=
 FVAR(1)
 Sof(C21A)=Sof(H21D)=Sof(H21E)=Sof(H21F)=Sof(C22A)=Sof(H22D)=Sof(H22E)=
 Sof(H22F)=1-FVAR(2)
 Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=
 FVAR(2)
 Sof(H56A)=Sof(H56B)=Sof(C57A)=Sof(H57A)=Sof(H57B)=Sof(C58A)=Sof(H58A)=
 Sof(H58B)=Sof(H58C)=1-FVAR(3)
 Sof(H56C)=Sof(H56D)=Sof(C57)=Sof(H57C)=Sof(H57D)=Sof(C58)=Sof(H58D)=Sof(H58E)=
 Sof(H58F)=FVAR(3)
6.a Ternary CH refined with riding coordinates:
 C12(H12), C13(H13), C41(H41), C42(H42)
6.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C14(H14A,H14B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B),
 C28(H28A,H28B), C38(H38A,H38B), C43(H43A,H43B), C54(H54A,H54B), C55(H55A,H55B),
  C56(H56C,H56D), C56(H56A,H56B), C57A(H57A,H57B), C57(H57C,H57D)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C10(H10), C30(H30), C31(H31),
 C32(H32), C33(H33), C36(H36), C37(H37), C39(H39)
6.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C), C21A(H21D,H21E,H21F), C22A(H22D,H22E,H22F),
 C23A(H23D,H23E,H23F), C24A(H24D,H24E,H24F), C50(H50A,H50B,H50C), C51(H51A,H51B,
 H51C), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C), C58A(H58A,H58B,H58C),
 C58(H58D,H58E,H58F)
;
_shelx_res_checksum              47308
_olex2_submission_special_instructions 'No special instructions were received'