Microwave assisted domino heck cyclization and alkynylation: synthesis of alkyne substituted dihydrobenzofurans
Karu, Ramesh; Gedu, Satyanarayana; Green Chemistry 20 (2018) 369–; doi:10.1039/C7GC02606D

data_7229415
_publ_section_title
;
 Microwave assisted domino heck cyclization and alkynylation: synthesis of
 alkyne substituted dihydrobenzofurans
;
_journal_issue                   2
_journal_name_full               'Green Chemistry'
_journal_page_first              369
_journal_paper_doi               10.1039/C7GC02606D
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C19 H19 N O'
_chemical_formula_sum            'C19 H19 N O'
_chemical_formula_weight         277.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_primary     direct
_audit_creation_date             2017-08-22
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-08-24 deposited with the CCDC.
2017-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.511(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0947(4)
_cell_length_b                   5.86763(14)
_cell_length_c                   18.4634(5)
_cell_measurement_reflns_used    2441
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.3110
_cell_measurement_theta_min      4.8240
_cell_volume                     1513.87(7)
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9776
_diffrn_measured_fraction_theta_max 0.9776
_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     20.00  69.00   1.00    1.90    --    0.00  57.00  30.00   49
  2  \w     82.00 123.00   1.00    7.61    --   54.00  57.00 -90.00   41
  3  \w    130.00 175.00   1.00    7.61    --  108.00 111.00-180.00   45
  4  \w    122.00 176.00   1.00    7.61    --  108.00  38.00-150.00   54
  5  \w     83.00 176.00   1.00    7.61    --  108.00  64.00 -90.00   93
  6  \w     77.00 149.00   1.00    7.61    --  108.00 178.00-150.00   72
  7  \w    -15.00  68.00   1.00    7.61    --   54.00 -57.00 120.00   83
  8  \w     29.00 110.00   1.00    7.61    --   54.00-125.00 120.00   81
  9  \w     68.00  93.00   1.00    7.61    --  108.00-111.00  30.00   25
 10  \w     40.00  91.00   1.00    7.61    --  108.00-111.00 -30.00   51
 11  \w     38.00 131.00   1.00    7.61    --  108.00 -50.00 120.00   93
 12  \w    -11.00  75.00   1.00    7.61    --   54.00 -57.00-150.00   86
 13  \w     63.00 115.00   1.00    7.61    --  108.00-111.00-180.00   52
 14  \w    -66.00 -16.00   1.00    1.90    --    0.00 -57.00 -90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0937714000
_diffrn_orient_matrix_UB_12      0.1050760000
_diffrn_orient_matrix_UB_13      -0.0378569000
_diffrn_orient_matrix_UB_21      -0.0301458000
_diffrn_orient_matrix_UB_22      0.0573529000
_diffrn_orient_matrix_UB_23      0.0751661000
_diffrn_orient_matrix_UB_31      0.0495646000
_diffrn_orient_matrix_UB_32      0.2335847000
_diffrn_orient_matrix_UB_33      -0.0014117000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            4979
_diffrn_reflns_theta_full        69.8959
_diffrn_reflns_theta_max         69.90
_diffrn_reflns_theta_min         4.83
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.581
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75237
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2169
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             593.7117
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.3144
_refine_diff_density_min         -0.3126
_refine_diff_density_rms         0.0874
_refine_ls_d_res_high            0.8209
_refine_ls_d_res_low             9.1525
_refine_ls_goodness_of_fit_ref   1.2425
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    31
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2797
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.2425
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0581
_refine_ls_shift/su_max          0.08
_refine_ls_shift/su_mean         0.0052
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1844
_refine_ls_wR_factor_ref         0.2002
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -17
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                2065
_reflns_number_total             2797
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c7gc02606d2.cif
_cod_data_source_block           exp_8633
_cod_depositor_comments
;

2018-03-15
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel

 Adding full bibliography for 7229415.cif.
;
_cod_original_formula_moiety     '1.33(C19 H19 N O)'
_cod_original_formula_sum        'C25.333 H25.333 N1.333 O1.333'
_cod_original_formula_units_Z    3
_cod_original_formula_weight     369.82
_cod_database_code               7229415
_chemical_oxdiff_formula         'C23 N2 H14 O2'
_reflns_odcompleteness_completeness 99.46
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N1(H1a,H1b)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C11(H11a,H11b)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C17(H17), C19(H19), C2(H2), C16(H16), C3(H3), C15(H15)
2.d Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C7(H7a,H7b,H7c)
;
_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 6.569
_oxdiff_exptl_absorpt_empirical_full_min 0.702