Organocatalytic allylic alkylation of alkyne-substituted MBH carbonates: access to quaternary carbon-containing 1,4-enynes.
Li, Yu; Wang, Mei; Ma, Rongrong; Niu, Rui; Wang, Haodong; Zhang, Yantu; Lin, Jun-Bing; Organic & biomolecular chemistry 21 (2023) 8263–8266; doi:10.1039/d3ob01317k

data_7159579
_publ_section_title
;
 Organocatalytic allylic alkylation of alkyne-substituted MBH carbonates:
 access to quaternary carbon-containing 1,4-enynes.
;
_journal_issue                   41
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8263
_journal_page_last               8266
_journal_paper_doi               10.1039/d3ob01317k
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C19 H21 N O8'
_chemical_formula_sum            'C19 H21 N O8'
_chemical_formula_weight         391.37
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-23
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-12-26 deposited with the CCDC.	2023-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                102.672(11)
_cell_angle_beta                 97.280(12)
_cell_angle_gamma                94.451(7)
_cell_formula_units_Z            8
_cell_length_a                   9.065(2)
_cell_length_b                   14.720(3)
_cell_length_c                   31.665(9)
_cell_measurement_reflns_used    8047
_cell_measurement_temperature    193
_cell_measurement_theta_max      27.01
_cell_measurement_theta_min      2.46
_cell_volume                     4064.8(17)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX4 V2022.1-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      193
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON 100'
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE TXS PHOTON 100'
_diffrn_measurement_method       '\w and \f shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0775
_diffrn_reflns_av_unetI/netI     0.1307
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            34644
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.599
_diffrn_reflns_theta_min         1.712
_diffrn_source                   TXS
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_type              'Rotaing Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1300 before and 0.0923 after correction.
The Ratio of minimum to maximum transmission is 0.6555.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       block
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1066
_refine_ls_number_reflns         18223
_refine_ls_number_restraints     76
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1931
_refine_ls_R_factor_gt           0.1110
_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^)+(0.1555P)^2^+2.7208P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2854
_refine_ls_wR_factor_ref         0.3516
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8959
_reflns_number_total             18223
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01317k2.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7159578--7159579.cif.
;
_cod_original_cell_volume        4064.9(18)
_cod_database_code               7159579
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.987
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.677(3)
 0.323(3)
2. 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
3. Restrained distances
 O18-C41 \\sim O18A-C41
 with sigma of 0.02
 O18-C40 \\sim O18A-C40A
 with sigma of 0.02
 O9-C24 \\sim O9A-C24
 with sigma of 0.02
 O9A-C20A \\sim O9-C20
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
O9A \\sim C20A \\sim O9 \\sim C20: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
O18A \\sim O18 \\sim C40A \\sim C40: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
5. Others
 Sof(O18A)=Sof(C40A)=Sof(H40D)=Sof(H40E)=Sof(H40F)=1-FVAR(1)
 Sof(O18)=Sof(C40)=Sof(H40A)=Sof(H40B)=Sof(H40C)=FVAR(1)
 Sof(O9A)=Sof(C20A)=Sof(H20A)=Sof(H20B)=Sof(H20C)=1-FVAR(2)
 Sof(O9)=Sof(C20)=Sof(H20D)=Sof(H20E)=Sof(H20F)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C50(H50A,H50B), C31(H31A,H31B), C69(H69A,H69B), C52(H52A,
 H52B), C33(H33A,H33B), C14(H14A,H14B), C71(H71A,H71B)
6.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C44(H44), C27(H27), C63(H63), C3(H3), C61(H61), C46(H46), C65(H65),
 C5(H5), C42(H42), C23(H23), C25(H25)
6.c X=CH2 refined with riding coordinates:
 C55(H55A,H55B), C36(H36A,H36B), C17(H17A,H17B), C74(H74A,H74B)
6.d Idealised Me refined as rotating group:
 C53(H53A,H53B,H53C), C39(H39A,H39B,H39C), C72(H72A,H72B,H72C), C15(H15A,H15B,
 H15C), C21(H21A,H21B,H21C), C59(H59A,H59B,H59C), C34(H34A,H34B,H34C), C58(H58A,
 H58B,H58C), C1(H1A,H1B,H1C), C19(H19A,H19B,H19C), C8(H8A,H8B,H8C), C38(H38A,
 H38B,H38C), C76(H76A,H76B,H76C), C57(H57A,H57B,H57C), C40(H40A,H40B,H40C),
 C40A(H40D,H40E,H40F), C20A(H20A,H20B,H20C), C20(H20D,H20E,H20F)
;
_shelx_res_checksum              93200
_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU