Synthesis of cyclopentaquinolinone and cyclopentapyridinone from ortho-alkynyl-N-arylaldehyde via superbase-promoted C-N, C-O and C-C bond formation.
Saini, Kapil Mohan; Saunthwal, Rakesh K.; Sushmita, ?; Verma, Akhilesh K.; Organic & biomolecular chemistry 18 (2020) 5594–5601; doi:10.1039/d0ob01281e

data_7157567
_publ_section_title
;
 Synthesis of cyclopentaquinolinone and cyclopentapyridinone from
 ortho-alkynyl-N-arylaldehyde via superbase-promoted C-N, C-O and C-C bond
 formation.
;
_journal_issue                   29
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5594
_journal_page_last               5601
_journal_paper_doi               10.1039/d0ob01281e
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C25 H17 F N2 O, H2 O'
_chemical_formula_sum            'C25 H19 F N2 O2'
_chemical_formula_weight         398.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-16 deposited with the CCDC.	2020-06-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.491(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.1550(5)
_cell_length_b                   15.2830(11)
_cell_length_c                   10.6069(9)
_cell_measurement_reflns_used    1143
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.3300
_cell_measurement_theta_min      3.8310
_cell_volume                     994.69(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'four-circle diffractometer'
_diffrn_measurement_method       'Xcalibur, Sapphire3'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0988
_diffrn_reflns_av_unetI/netI     0.0872
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13752
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         3.320
_exptl_absorpt_coefficient_mu    0.091
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       Block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4052
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0987
_refine_ls_R_factor_gt           0.0579
_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^)+(0.0424P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1348
_reflns_Friedel_coverage         0.923
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2587
_reflns_number_total             4052
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01281e2.cif
_cod_data_source_block           kms-1132
_cod_depositor_comments          'Adding full bibliography for 7157567.cif.'
_cod_database_code               7157567
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.998
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0(2)
 1(2)
2. 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, All O(H,H) groups
3.a Free rotating group:
 O002(H00D,H00E)
3.b Aromatic/amide H refined with riding coordinates:
 N003(H003), C007(H007), C00F(H00F), C00G(H00G), C00I(H00I), C00K(H00K),
 C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00T(H00T)
3.c Idealised Me refined as rotating group:
 C00U(H00A,H00B,H00C)
;
_shelx_res_checksum              78604
_olex2_submission_special_instructions 'No special instructions were received'