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_7127199
_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 H18 N2 O'
_chemical_formula_sum            'C22 H18 N2 O'
_chemical_formula_weight         326.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 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                90
_cell_angle_beta                 99.361(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.602(3)
_cell_length_b                   13.685(3)
_cell_length_c                   19.401(4)
_cell_measurement_reflns_used    6724
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.22
_cell_measurement_theta_min      2.26
_cell_volume                     3563.3(13)
_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      293(2)
_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_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12571
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         2.125
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0103(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0486
_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^)+(0.0825P)^2^+2.1671P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1557
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2732
_reflns_number_total             3323
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc05363e2.cif
_cod_data_source_block           y
_cod_depositor_comments
'Adding full bibliography for 7127198--7127199.cif.'
_cod_original_cell_volume        3563.2(12)
_cod_database_code               7127199
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.985
_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 Aromatic/amide H refined with riding coordinates: 
 C3(H3), C4(H4), C7(H7), C10(H10), C12(H12), C13(H13), C18(H18), C19(H19), 
 C20(H20), C21(H21), C22(H22), N1(H1) 
2.b Idealised Me refined as rotating group: 
 C1(H1A,H1B,H1C), C15(H15A,H15B,H15C) 
;
_olex2_submission_special_instructions 'No special instructions were received'