Chemoselective tandem SN2'/SN2''/inter- or intramolecular Diels-Alder reaction of γ-vinyl MBH carbonates with phenols and o-hydroxychalcones
Liu, Wei; Zhang, Le; Liu, Ye; Fan, Shilu; Dai, Jian-Jun; Tao, Wei; Zhu, Huixia; Xiao, Hua; Chemical Communications  (2022) –; doi:10.1039/D2CC03771H

data_7130503
_publ_section_title
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 Chemoselective tandem SN2'/SN2''/inter- or intramolecular Diels-Alder
 reaction of \g-vinyl MBH carbonates with phenols and o-hydroxychalcones
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_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03771H
_journal_year                    2022
_chemical_formula_moiety         'C22 H19 Br O4'
_chemical_formula_sum            'C22 H19 Br O4'
_chemical_formula_weight         427.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-01
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-07-02 deposited with the CCDC.	2022-08-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.7751(17)
_cell_length_b                   15.553(2)
_cell_length_c                   20.306(3)
_cell_measurement_reflns_used    8674
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      26.809
_cell_measurement_theta_min      2.389
_cell_volume                     3718.8(9)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            29713
_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         27.703
_diffrn_reflns_theta_min         2.006
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.236
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1160 before and 0.0444 after correction.
The Ratio of minimum to maximum transmission is 0.6021.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4351
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0408
_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^)+(0.0480P)^2^+2.4213P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1123
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3090
_reflns_number_total             4351
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03771h2.cif
_cod_data_source_block           220701b_0m
_cod_original_cell_volume        3718.9(9)
_cod_database_code               7130503
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.663
_shelx_estimated_absorpt_t_min   0.639
_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:
 C14(H14), C13(H13), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C18(H18), C4(H4), C11(H11), C21(H21), C22(H22), C10(H10), C8(H8),
 C9(H9)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              68890
_shelx_hkl_checksum              93839
_olex2_submission_special_instructions 'No special instructions were received'