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_4034294
_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         'C25 H19 N O3'
_chemical_formula_sum            'C25 H19 N O3'
_chemical_formula_weight         381.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-28
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.725(4)
_cell_length_b                   16.200(12)
_cell_length_c                   20.626(15)
_cell_measurement_reflns_used    309
_cell_measurement_temperature    173
_cell_measurement_theta_max      18.087
_cell_measurement_theta_min      2.337
_cell_volume                     1913(2)
_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      173.0
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0861
_diffrn_reflns_av_unetI/netI     0.1596
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5556
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        24.724
_diffrn_reflns_theta_max         24.724
_diffrn_reflns_theta_min         1.598
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6162
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0645 before and 0.0483 after correction. The Ratio of minimum to maximum transmission is 0.8267. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.118
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   1(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3193
_refine_ls_number_restraints     216
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.1717
_refine_ls_R_factor_gt           0.0872
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1411P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2134
_refine_ls_wR_factor_ref         0.2746
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                1645
_reflns_number_total             3193
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03210_si_002.cif
_cod_data_source_block           mo_20180659_0m
_cod_database_code               4034294
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0(4)
 1(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 C21(H21), C25(H25), C12(H12), C17(H17), C22(H22), C24(H24), C14(H14),
 C23(H23), C13(H13), C1(H1), C15(H15), C4(H4), C3(H3A), C5(H5), C2(H2)
4.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
4.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'