Base-Promoted Cascade Reactions of 3-(1-Alkynyl)chromones with Pyridinium Ylides to Chromeno[2,3- d]azepine Derivatives.
Zhang, Yu-Fang; Duan, Wen-Di; Chen, Jingjing; Hu, Youhong; The Journal of organic chemistry 84 (2019) 4467–4472; doi:10.1021/acs.joc.8b03210

data_4034293
_publ_section_title
;
 Base-Promoted Cascade Reactions of 3-(1-Alkynyl)chromones with Pyridinium
 Ylides to Chromeno[2,3- d]azepine Derivatives.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4467
_journal_page_last               4472
_journal_paper_doi               10.1021/acs.joc.8b03210
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C H2 Cl2, C24 H16 N2 O2'
_chemical_formula_sum            'C25 H18 Cl2 N2 O2'
_chemical_formula_weight         449.31
_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     dual
_audit_creation_date             2018-06-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                106.973(5)
_cell_angle_beta                 99.530(5)
_cell_angle_gamma                100.043(5)
_cell_formula_units_Z            2
_cell_length_a                   8.3323(18)
_cell_length_b                   10.241(2)
_cell_length_c                   13.709(3)
_cell_measurement_reflns_used    959
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      21.070
_cell_measurement_theta_min      2.550
_cell_volume                     1072.2(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      173.15
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.0853
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.985
_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       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9013
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.400
_diffrn_reflns_theta_min         1.596
_exptl_absorpt_coefficient_mu    0.328
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6274
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0744 before and 0.0548 after correction. The Ratio of minimum to maximum transmission is 0.8417. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.008(3)
_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   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4343
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1154
_refine_ls_R_factor_gt           0.0674
_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^)+(0.0916P)^2^+0.3324P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1675
_refine_ls_wR_factor_ref         0.2112
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2532
_reflns_number_total             4343
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03210_si_001.cif
_cod_data_source_block           mo_20180600-zyf_0m
_cod_database_code               4034293
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.943
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C9(H9), C15(H15), C23(H23), C12(H12), C20(H20), C1(H1), C4(H4),
 C14(H14), C21(H21), C2(H2), C3(H3), C13(H13), C22(H22)
;
_olex2_submission_special_instructions 'No special instructions were received'