Solvent-controlled divergent annulation of ynones and (iso)quinoline N-oxides: of 3-((iso)quinolin-1-yl)-4H-chromen-4-ones and 13H-isoquinolino[2,1-a]quinolin-13-ones.
Yang, Wan-Wan; Chen, Lu-Lu; Chen, Pei; Ye, Ya-Fang; Wang, Yan-Bo; Zhang, Xiao; Chemical communications (Cambridge, England) 56 (2020) 1183–1186; doi:10.1039/c9cc08713c

data_7125661
_publ_section_title
;
 Solvent-controlled divergent annulation of ynones and (iso)quinoline
 N-oxides: of 3-((iso)quinolin-1-yl)-4H-chromen-4-ones and
 13H-isoquinolino[2,1-a]quinolin-13-ones.
;
_journal_issue                   8
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1183
_journal_page_last               1186
_journal_paper_doi               10.1039/c9cc08713c
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C25 H18 Br N O2'
_chemical_formula_sum            'C25 H18 Br N O2'
_chemical_formula_weight         444.31
_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             2019-10-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-16 deposited with the CCDC.	2019-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                77.759(8)
_cell_angle_beta                 88.648(9)
_cell_angle_gamma                85.507(8)
_cell_formula_units_Z            4
_cell_length_a                   7.411(2)
_cell_length_b                   12.752(4)
_cell_length_c                   21.926(6)
_cell_measurement_reflns_used    3771
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.80
_cell_measurement_theta_min      2.23
_cell_volume                     2018.7(10)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      298.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_av_unetI/netI     0.1051
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            31422
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.331
_diffrn_reflns_theta_min         2.233
_exptl_absorpt_coefficient_mu    2.057
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0955 before and 0.0614 after correction. The Ratio of minimum to maximum transmission is 0.8137. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.036
_refine_diff_density_min         -0.996
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     525
_refine_ls_number_reflns         9993
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1752
_refine_ls_R_factor_gt           0.0627
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0801P)^2^+0.1978P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1480
_refine_ls_wR_factor_ref         0.1901
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4350
_reflns_number_total             9993
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc08713c2.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 7125659--7125661.cif.'
_cod_original_cell_volume        2018.8(10)
_cod_database_code               7125661
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.869
_shelx_estimated_absorpt_t_min   0.748
_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. Rigid bond restraints
 C4', C5'
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C5', C6'
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C2', C1'
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C5') \\sim Ueq, Uanis(C4') \\sim Ueq, Uanis(C3') \\sim Ueq, Uanis(C2')
\\sim Ueq, Uanis(C1') \\sim Ueq, Uanis(C6') \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C14(H14), C15(H15),
 C18(H18), C19(H19), C22(H22), C23(H23), C24(H24), C25(H25), N1(H1), C2'(H2'),
 C3'(H3'), C4'(H4'), C5'(H5'), C11'(H11'), C12'(H12'), C14'(H14'), C15'(H15'),
 C18'(H18'), C19'(H19'), C22'(H22'), C23'(H23'), C24'(H24'), C25'(H25'),
 N1'(H1')
4.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C16'(H16D,H16E,H16F)
;
_olex2_submission_special_instructions 'No special instructions were received'