Copper-catalyzed asymmetric 1,6-conjugate addition of in situ generated para-quinone methides with β-ketoesters
Wang, Yifeng; Wang, Chao-Jie; Feng, Qing-Zhou; Zhai, Jing-Jing; Qi, Suosuo; Zhong, Ai-Guo; Chu, Mingming; Xu, Dan-Qian; Chemical Communications  (2022) –; doi:10.1039/D2CC00146B

data_7130083
_publ_section_title
;
 Copper-catalyzed asymmetric 1,6-conjugate addition of in situ generated
 para-quinone methides with \b-ketoesters
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC00146B
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H18 Cl O4, C H4 O'
_chemical_formula_sum            'C25 H22 Cl O5'
_chemical_formula_weight         437.87
_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             2022-03-31
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-04-11 deposited with the CCDC.	2022-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1420(11)
_cell_length_b                   11.4280(15)
_cell_length_c                   22.2670(19)
_cell_measurement_reflns_used    359
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      43.309
_cell_measurement_theta_min      13.148
_cell_volume                     2326.3(5)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX3 V2019.11-0 (Bruker, 2019)'
_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      173.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1189
_diffrn_reflns_av_unetI/netI     0.0858
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20073
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.210
_diffrn_reflns_theta_min         5.230
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_type              'Incoatec I\ms DIAMOND'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.723
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.4996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1515 before and 0.0996 after correction.
The Ratio of minimum to maximum transmission is 0.6623.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_description       block
_exptl_crystal_F_000             916
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 959 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.080(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0690
_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^)+(0.1263P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1784
_refine_ls_wR_factor_ref         0.2075
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.906
_reflns_number_gt                3056
_reflns_number_total             4711
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc00146b2.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 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7130083
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.847
_shelx_estimated_absorpt_t_min   0.820
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C6(H6), C13(H13), C12(H12), C5(H5), C2(H2), C9(H9), C19(H19),
 C3(H3), C11(H11), C22(H22), C10(H10), C21(H21)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C25(H25A,H25B,H25C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_shelx_res_checksum              6412
_olex2_submission_special_instructions 'No special instructions were received'