Electro-carbo-cyclization of alkyne-, alkene-, and nitrile-tethered α-halocarbonyls.
Ghosh, Subhadeep; Biswas, Sumit; Das, Indrajit; Chemical communications (Cambridge, England) 61 (2025) 17448–17451; doi:10.1039/d5cc04237b

data_7135057
_publ_section_title
;
 Electro-carbo-cyclization of alkyne-, alkene-, and nitrile-tethered
 &#x3b1;-halocarbonyls.
;
_journal_issue                   89
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              17448
_journal_page_last               17451
_journal_paper_doi               10.1039/d5cc04237b
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C21 H25 N O'
_chemical_formula_sum            'C21 H25 N O'
_chemical_formula_weight         307.42
_chemical_name_systematic        SMB_5_111A
_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     iterative
_audit_creation_date             2025-01-29
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2025.01.22 svn.rc7346086 for OlexSys, GUI svn.r7128)
;
_audit_update_record
;
2025-05-31 deposited with the CCDC.	2025-09-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4002(2)
_cell_length_b                   10.6999(2)
_cell_length_c                   17.6147(4)
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      66.64
_cell_measurement_theta_min      4.84
_cell_volume                     1771.71(6)
_computing_cell_refinement       'Bruker SAINT V8.38A (Bruker AXS)'
_computing_data_collection       'Bruker APEX3 ver.2018.7-2(Bruker AXS)'
_computing_data_reduction        'Bruker SAINT V8.38A (Bruker AXS)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    '0.5 mm double-pinhole'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            31265
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.638
_diffrn_reflns_theta_max         66.638
_diffrn_reflns_theta_min         4.836
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms Diamond'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.538
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1231 before and 0.0612 after correction.
The Ratio of minimum to maximum transmission is 0.8702.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.153
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.099
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 1205 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(9)
_refine_ls_extinction_coef       0.0086(9)
_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   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3109
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0339
_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^)+(0.0506P)^2^+0.1237P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0900
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                2994
_reflns_number_total             3109
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04237b2.cif
_cod_data_source_block           smb_5_111a_0m_a
_cod_depositor_comments          'Adding full bibliography for 7135057.cif.'
_cod_database_code               7135057
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.938
_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), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C21(H21A,H21B,
 H21C)
;
_shelx_res_checksum              97158
_shelx_hkl_checksum              30237
_olex2_submission_original_sample_id SMB_5_111A
_olex2_submission_special_instructions 'No special instructions were received'