KOtBu-promoted Michael/aldol/ring-opening cascade reaction of cyclobutanones with chalcones
Wang, Biao; Zhong, Han; Tian, Xu; Chemical Communications  (2022) –; doi:10.1039/D2CC03007A

data_7130439
_publ_section_title
;
 KOtBu-promoted Michael/aldol/ring-opening cascade reaction of
 cyclobutanones with chalcones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC03007A
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H22 Br Cl O2'
_chemical_formula_sum            'C26 H22 Br Cl O2'
_chemical_formula_weight         481.79
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-03-02 deposited with the CCDC.	2022-07-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.0573(7)
_cell_length_b                   18.127(2)
_cell_length_c                   33.894(4)
_cell_measurement_reflns_used    5170
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      22.69
_cell_measurement_theta_min      2.55
_cell_volume                     4336.0(8)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_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  0.0498
_diffrn_reflns_av_unetI/netI     0.0923
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            26041
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.453
_diffrn_reflns_theta_min         1.274
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.040
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5037
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0980 before and 0.0578 after correction.
The Ratio of minimum to maximum transmission is 0.6756.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_description       block
_exptl_crystal_F_000             1968
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
;
 Flack x determined using 2215 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.006(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     543
_refine_ls_number_reflns         9783
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0418
_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^)+(0.0456P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.1079
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                6697
_reflns_number_total             9783
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03007a2.cif
_cod_data_source_block           210825tx_0m
_cod_database_code               7130439
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.822
_shelx_estimated_absorpt_t_min   0.686
_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:
 C009(H009), C00D(H00F), C00F(H00G), C00L(H00L), C00O(H00O), C01D(H01L)
2.b Secondary CH2 refined with riding coordinates:
 C00U(H00D,H00E), C013(H01D,H01F)
2.c Aromatic/amide H refined with riding coordinates:
 C00K(H00K), C00N(H00N), C00R(H00R), C00S(H00S), C00T(H00T), C00V(H00V),
 C00W(H00W), C00Y(H00Y), C00Z(H00Z), C012(H012), C014(H014), C015(H015),
 C016(H016), C019(H019), C01A(H01G), C01B(H01I), C01C(H01J), C01E(H01E),
 C01F(H01M), C01G(H01N), C01H(H01H), C01I(H01O), C01J(H01P), C01K(H01K),
 C01L(H01Q), C01M(H01R), C01N(H01S), C01O(H01T)
2.d Idealised Me refined as rotating group:
 C00B(H00A,H00B,H00C), C010(H01A,H01B,H01C)
;
_shelx_res_checksum              50402
_shelx_hkl_checksum              38925
_olex2_submission_special_instructions 'No special instructions were received'