Remote asymmetric conjugate addition of naphthoquinone methides: constructing adjacent tertiary-quaternary carbon stereocenters.
Zhai, Jing-Jing; Lou, Shao-Jie; Zhang, Xiao-Xiao; Lan, Qiu-Yi; Jing, Cheng-Cheng; Mao, Yang-Jie; Wang, Yi-Feng; Chu, Ming-Ming; Xu, Dan-Qian; Chemical communications (Cambridge, England) 61 (2025) 16644–16647; doi:10.1039/d5cc03265b

data_7134992
_publ_section_title
;
 Remote asymmetric conjugate addition of naphthoquinone methides:
 constructing adjacent tertiary-quaternary carbon stereocenters.
;
_journal_issue                   85
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              16644
_journal_page_last               16647
_journal_paper_doi               10.1039/d5cc03265b
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H20 Br O4, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C28.5 H21 Br Cl O4'
_chemical_formula_weight         542.81
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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             2022-10-25
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-02-24 deposited with the CCDC.	2025-09-11 downloaded from the CCDC.
;
_cell_angle_alpha                106.141(2)
_cell_angle_beta                 96.303(2)
_cell_angle_gamma                107.287(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0354(5)
_cell_length_b                   11.1067(6)
_cell_length_c                   13.6619(8)
_cell_measurement_reflns_used    5166
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.31
_cell_measurement_theta_min      2.41
_cell_volume                     1229.51(12)
_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      296.15
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON 100'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE 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  0.0286
_diffrn_reflns_av_unetI/netI     0.0698
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11336
_diffrn_reflns_point_group_measured_fraction_full 0.682
_diffrn_reflns_point_group_measured_fraction_max 0.671
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.516
_diffrn_reflns_theta_min         2.032
_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    1.814
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0993 before and 0.0657 after correction.
The Ratio of minimum to maximum transmission is 0.8872.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.724
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 1471 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.080(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     626
_refine_ls_number_reflns         7613
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0472
_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^)+(0.0359P)^2^+0.9032P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1172
_reflns_Friedel_coverage         0.353
_reflns_Friedel_fraction_full    0.372
_reflns_Friedel_fraction_max     0.351
_reflns_number_gt                6455
_reflns_number_total             7613
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc03265b2.cif
_cod_data_source_block           221021li_lidz173796_1_0m
_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 7134992--7134994.cif.
;
_cod_original_formula_sum        'C28.50 H21 Br Cl O4'
_cod_database_code               7134992
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.839
_shelx_estimated_absorpt_t_min   0.798
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C39(H39), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C57(H57A,H57B)
2.c Aromatic/amide H refined with riding coordinates:
 C54(H54), C45(H45), C10(H10), C26(H26), C13(H13), C49(H49), C14(H14),
 C33(H33), C5(H5), C31(H31), C21(H21), C41(H41), C44(H44), C15(H15), C52(H52),
 C42(H42), C51(H51), C23(H23), C8(H8A), C7(H7), C17(H17), C35(H35), C43(H43),
 C30(H30), C36(H36), C2(H2), C3(H3), C24(H24), C38(H38), C16(H16)
2.d Idealised Me refined as rotating group:
 C48(H48A,H48B,H48C), C20(H20A,H20B,H20C)
2.e Idealised tetrahedral OH refined as rotating group:
 O8(H8), O4(H4)
;
_shelx_res_checksum              117
_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU