Step-wise and one-pot synthesis of highly substituted conjugated trienes from 2-oxobenzo[<i>h</i>]chromenes/2<i>H</i>-pyran-2-ones.
Elagamy, Amr; Althagafi, Ismail; Pratap, Ramendra; Organic & biomolecular chemistry 19 (2021) 3901–3910; doi:10.1039/d1ob00314c

data_7158007
_publ_section_title
;
 Step-wise and one-pot synthesis of highly substituted conjugated trienes
 from 2-oxobenzo[<i>h</i>]chromenes/2<i>H</i>-pyran-2-ones.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3901
_journal_page_last               3910
_journal_paper_doi               10.1039/d1ob00314c
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C20 H22 N2'
_chemical_formula_sum            'C20 H22 N2'
_chemical_formula_weight         290.39
_chemical_name_systematic        'conjugated triene'
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-11-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-03 deposited with the CCDC.	2021-04-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.706(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2510(2)
_cell_length_b                   18.8202(6)
_cell_length_c                   14.2270(5)
_cell_measurement_reflns_used    3697
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5470
_cell_measurement_theta_min      3.9350
_cell_volume                     1654.45(10)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9853
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w      5.00  88.00   1.00    3.50    --   19.15  57.00   0.00   83
  2  \w      3.00  88.00   1.00    3.50    --   19.15  57.00 -90.00   85
  3  \w      7.00  88.00   1.00    3.50    --   19.15  57.00-180.00   81
  4  \w    -25.00  60.00   1.00    3.50    --   19.15 -99.00-150.00   85
  5  \w    -21.00  60.00   1.00    3.50    --   19.15 -99.00  30.00   81
  6  \w    -25.00  56.00   1.00    3.50    --   19.15 -99.00 120.00   81
  7  \w      4.00  78.00   1.00    3.50    --   19.15  57.00  90.00   74
  8  \w    -47.00  37.00   1.00    3.50    --   19.15 -38.00-120.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0172032000
_diffrn_orient_matrix_UB_12      -0.0372345000
_diffrn_orient_matrix_UB_13      -0.0008593000
_diffrn_orient_matrix_UB_21      0.0071682000
_diffrn_orient_matrix_UB_22      0.0018831000
_diffrn_orient_matrix_UB_23      -0.0492294000
_diffrn_orient_matrix_UB_31      0.1132440000
_diffrn_orient_matrix_UB_32      0.0055243000
_diffrn_orient_matrix_UB_33      0.0109844000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11420
_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         27.096
_diffrn_reflns_theta_min         3.470
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3615
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0761
_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^)+(0.0982P)^2^+1.6368P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2068
_refine_ls_wR_factor_ref         0.2139
_reflns_Friedel_coverage         0.994
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3167
_reflns_number_total             3615
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00314c2.cif
_cod_data_source_block           aeb-28
_cod_depositor_comments
'Adding full bibliography for 7158006--7158007.cif.'
_cod_database_code               7158007
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C21 H22 N2 O2'
_chemical_oxdiff_usercomment     25-01-2018
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.985
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C20(H20A,H20B), C18(H18A,H18B), C17(H17A,H17B),
 C19(H19A,H19B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C5(H5), C2(H2), C3(H3), C4(H4)
2.c X=CH2 refined with riding coordinates:
 C12(H12A,H12B)
;
_shelx_res_checksum              84458
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.196
_oxdiff_exptl_absorpt_empirical_full_min 0.736