Dienylation of <i>N</i>-benzoylhydrazones with CF<sub>3</sub>-substituted homoallenylboronates in water.
Ma, Wei-Wei; Yang, Chao; Xie, Qiang; Xu, Yun-He; Organic & biomolecular chemistry 20 (2022) 1386–1390; doi:10.1039/d1ob02335g

data_7158504
_publ_section_title
;
 Dienylation of <i>N</i>-benzoylhydrazones with CF<sub>3</sub>-substituted
 homoallenylboronates in water.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1386
_journal_page_last               1390
_journal_paper_doi               10.1039/d1ob02335g
_journal_volume                  20
_journal_year                    2022
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C22 H23 F3 N2 O'
_chemical_formula_sum            'C22 H23 F3 N2 O'
_chemical_formula_weight         388.42
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_Hall           'R 3 -2"c'
_space_group_name_H-M_alt        'R 3 c :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-11-08 deposited with the CCDC.	2022-01-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   32.7473(4)
_cell_length_b                   32.7473(4)
_cell_length_c                   9.72720(10)
_cell_measurement_reflns_used    9864
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      53.983
_cell_measurement_theta_min      4.700
_cell_volume                     9033.78(18)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.04
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            32549
_diffrn_reflns_point_group_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.925
_diffrn_reflns_theta_min         4.699
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.529
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1273 before and 0.0610 after correction. The Ratio of minimum to maximum transmission is 0.8262. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       block
_exptl_crystal_F_000             3672
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.108
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1287 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3536
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0336
_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^)+(0.0378P)^2^+1.8553P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0771
_reflns_Friedel_coverage         0.845
_reflns_Friedel_fraction_full    0.858
_reflns_Friedel_fraction_max     0.852
_reflns_number_gt                3163
_reflns_number_total             3536
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02335g2.cif
_cod_data_source_block           190920mww_0m
_cod_depositor_comments          'Adding full bibliography for 7158504.cif.'
_cod_original_cell_volume        9033.8(2)
_cod_original_sg_symbol_H-M      'R 3 c'
_cod_database_code               7158504
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.939
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              48568
_olex2_submission_special_instructions 'No special instructions were received'