Metal-free radical bicyclization/chloroalkylarylation of 1,6-enynes with chloroalkanes.
Zhou, Hongxun; Li, Lijun; Yan, Qinqin; Ma, Jinyue; Wang, Ying; Gao, Yongjun; Liu, Zhong-Quan; Li, Zejiang; Chemical communications (Cambridge, England) 60 (2024) 3938–3941; doi:10.1039/d4cc00651h

data_7132824
_publ_section_title
;
 Metal-free radical bicyclization/chloroalkylarylation of 1,6-enynes with
 chloroalkanes.
;
_journal_issue                   29
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3938
_journal_page_last               3941
_journal_paper_doi               10.1039/d4cc00651h
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C19 H15 Cl O'
_chemical_formula_sum            'C19 H15 Cl O'
_chemical_formula_weight         294.76
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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             2023-12-29
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2024-02-03 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                73.280(5)
_cell_angle_beta                 88.509(5)
_cell_angle_gamma                71.049(5)
_cell_formula_units_Z            4
_cell_length_a                   9.6677(8)
_cell_length_b                   12.9019(11)
_cell_length_c                   13.3368(11)
_cell_measurement_reflns_used    4328
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      21.08
_cell_measurement_theta_min      2.65
_cell_volume                     1502.7(2)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (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 0.998
_diffrn_measured_fraction_theta_max 0.987
_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  0.0550
_diffrn_reflns_av_unetI/netI     0.0811
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            32550
_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         26.499
_diffrn_reflns_theta_min         1.599
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9158
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0952 before and 0.0519 after correction.
The Ratio of minimum to maximum transmission is 0.9158.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_F_000             616
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0046(16)
_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   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         6152
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1640
_refine_ls_R_factor_gt           0.0557
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0719P)^2^+0.0448P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1659
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2725
_reflns_number_total             6152
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00651h2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
Adding full bibliography for 7132822--7132824.cif.

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C38 H30 Cl2 O2'
_cod_original_formula_weight         589.52
_cod_original_formula_moiety         '2(C19 H15 Cl O)'
_cod_original_formula_units_Z            2
_cod_database_code               7132824
_shelx_shelxl_version_number     2018/3
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00G(H00D,H00E), C00I(H00A,H00C)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00H(H00H), C00J(H00J), C00K(H00K), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U),
 C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010),
 C011(H011), C012(H012), C013(H013), C014(H014), C015(H015), C016(H016)
2.c Idealised tetrahedral OH refined as rotating group:
 O003(H003), O004(H004)
;
_olex2_submission_special_instructions 'No special instructions were received'