Cross-coupling of amide and amide derivatives to umbelliferone nonaflates: synthesis of coumarin derivatives and fluorescent materials.
Hickey, Shane; Nitschke, Samuel; Sweetman, Martin Jay; Sumby, Christopher J.; Brooks, Douglas A.; Plush, Sally E.; Ashton, Trent D.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00813

data_4038435
_publ_section_title
;
 Cross-coupling of amide and amide derivatives to umbelliferone
 nonaflates: synthesis of coumarin derivatives and fluorescent materials.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00813
_journal_year                    2020
_chemical_formula_moiety         'C18 H15 N O4'
_chemical_formula_sum            'C18 H15 N O4'
_chemical_formula_weight         309.31
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-10
_audit_creation_method
;
Olex2 1.2
(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                   14.2902(2)
_cell_length_b                   15.0604(2)
_cell_length_c                   6.85110(10)
_cell_measurement_reflns_used    23799
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.1510
_cell_measurement_theta_min      3.9080
_cell_volume                     1474.47(4)
_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_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1695
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.842
_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    -25.00  61.00   1.00    9.00    --   18.95 -99.00 150.00   86
  2  \w    -54.00  92.00   1.00    9.00    --   18.95   0.00 120.00  146
  3  \w    -50.00  39.00   1.00    9.00    --   18.95 -57.00  60.00   89
  4  \w    -88.00   2.00   1.00    9.00    --  -19.50 -57.00-180.00   90
  5  \w    -84.00  -5.00   1.00    9.00    --  -19.50 137.00-163.00   79
  6  \w    -88.00   2.00   1.00    9.00    --  -19.50 -57.00 -90.00   90
  7  \w    -95.00 -35.00   1.00    9.00    --  -19.50-178.00-150.00   60
  8  \w    -25.00  22.00   1.00    9.00    --  -19.50 -99.00   0.00   47
  9  \w    -88.00   2.00   1.00    9.00    --  -19.50 -57.00  90.00   90
 10  \w    -50.00  51.00   1.00    9.00    --  -19.50  77.00   0.00  101
 11  \w    -54.00  92.00   1.00    9.00    --   18.95   0.00-120.00  146
 12  \w    -25.00  61.00   1.00    9.00    --   18.95 -99.00 -30.00   86
 13  \w      5.00  84.00   1.00    9.00    --   18.95-137.00 134.00   79
 14  \w     35.00  95.00   1.00    9.00    --   18.95 178.00 -90.00   60
 15  \w    -54.00  92.00   1.00    9.00    --   18.95   0.00-180.00  146
 16  \w    -54.00  92.00   1.00    9.00    --   18.95   0.00-150.00  146
 17  \w    -25.00  22.00   1.00    9.00    --  -19.50 -99.00 -60.00   47
 18  \w    -25.00  22.00   1.00    9.00    --  -19.50 -99.00  60.00   47
 19  \w    -54.00  92.00   1.00    9.00    --   18.95   0.00 -60.00  146
 20  \w    -54.00  92.00   1.00    9.00    --   18.95   0.00 -30.00  146
 21  \w    -54.00  40.00   1.00    9.00    --   18.95   0.00   0.00   94
 22  \w    -54.00  92.00   1.00    9.00    --   18.95   0.00 -90.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0121137000
_diffrn_orient_matrix_UB_12      0.0455716000
_diffrn_orient_matrix_UB_13      -0.0070148000
_diffrn_orient_matrix_UB_21      0.0471946000
_diffrn_orient_matrix_UB_22      -0.0118859000
_diffrn_orient_matrix_UB_23      -0.0186026000
_diffrn_orient_matrix_UB_31      -0.0094947000
_diffrn_orient_matrix_UB_32      -0.0009730000
_diffrn_orient_matrix_UB_33      -0.1015725000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.842
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            62797
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.814
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.862
_diffrn_reflns_theta_min         3.565
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96103
_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_density_diffrn    1.393
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1506 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3779
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0373
_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^)+(0.0659P)^2^+0.2549P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1021
_reflns_Friedel_coverage         0.795
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.783
_reflns_number_gt                3528
_reflns_number_total             3779
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00813_si_001.cif
_cod_data_source_block           smh11-085a
_cod_database_code               4038435
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C18H15O4N1
_chemical_oxdiff_usercomment     'colourless block 0.40 x 0.35 x 0.20'
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.961
_reflns_odcompleteness_completeness 99.44
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C3'(H3'), C4'(H4'), C5(H5), C5'(H5'), C6'(H6'), C7(H7), C8(H8),
 N11(H11)
2.b Idealised Me refined as rotating group:
 C8'(H8'A,H8'B,H8'C), C10(H10A,H10B,H10C)
;
_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 1.033
_oxdiff_exptl_absorpt_empirical_full_min 0.959