Arylacetylenes as two-carbon synthons: synthesis of eight-membered rings via C[triple bond, length as m-dash]C bond cleavage.
Zhao, Peng; Yu, Xiao-Xiao; Zhou, You; Huang, Chun; Wu, Yan-Dong; Zhu, Yan-Ping; Wu, An-Xin; Chemical communications (Cambridge, England) 56 (2020) 12554–12557; doi:10.1039/d0cc05363e

data_7127198
_publ_section_title
;
 Arylacetylenes as two-carbon synthons: synthesis of eight-membered rings
 via C[triple bond, length as m-dash]C bond cleavage.
;
_journal_issue                   83
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              12554
_journal_page_last               12557
_journal_paper_doi               10.1039/d0cc05363e
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C22 H17 Br N2 O, C H Cl3'
_chemical_formula_sum            'C23 H18 Br Cl3 N2 O'
_chemical_formula_weight         524.65
_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     direct
_audit_creation_date             2019-12-19
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_audit_update_record
;
2020-08-05 deposited with the CCDC.	2020-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                71.488(4)
_cell_angle_beta                 78.914(5)
_cell_angle_gamma                66.772(3)
_cell_formula_units_Z            2
_cell_length_a                   8.4050(19)
_cell_length_b                   10.003(2)
_cell_length_c                   15.623(4)
_cell_measurement_reflns_used    4811
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      29.67
_cell_measurement_theta_min      2.34
_cell_volume                     1141.2(5)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8078
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         1.379
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.170
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.3146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.667
_refine_diff_density_min         -1.064
_refine_diff_density_rms         0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4184
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0606
_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^)+(0.1090P)^2^+0.4675P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1644
_refine_ls_wR_factor_ref         0.1799
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3381
_reflns_number_total             4184
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc05363e2.cif
_cod_data_source_block           f
_cod_depositor_comments
'Adding full bibliography for 7127198--7127199.cif.'
_cod_database_code               7127198
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.812
_shelx_estimated_absorpt_t_min   0.781
_olex2_refinement_description
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(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: 
 C23(H23) 
2.b Aromatic/amide H refined with riding coordinates: 
 C3(H3), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C18(H18), C19(H19), 
 C21(H21), C22(H22), N1(H1) 
2.c Idealised Me refined as rotating group: 
 C1(H1A,H1B,H1C), C15(H15A,H15B,H15C) 
;
_olex2_submission_special_instructions 'No special instructions were received'