Praseodymium(III)-Catalyzed Regioselective Synthesis of C3-N-Substituted Coumarins with Coumarins and Azides.
Li, Jiu-Ling; Hu, Da-Chao; Liang, Xin-Ping; Wang, Ying-Chun; Wang, Heng-Shan; Pan, Ying-Ming; The Journal of organic chemistry 82 (2017) 9006–9011; doi:10.1021/acs.joc.7b01410

data_4032693
_publ_section_title
;
 Praseodymium(III)-Catalyzed Regioselective Synthesis of C3-N-Substituted
 Coumarins with Coumarins and Azides.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9006
_journal_page_last               9011
_journal_paper_doi               10.1021/acs.joc.7b01410
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C16 H13 N O2'
_chemical_formula_sum            'C16 H13 N O2'
_chemical_formula_weight         251.27
_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_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-11-17
_audit_creation_method
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Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
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_cell_angle_alpha                90
_cell_angle_beta                 95.595(5)
_cell_angle_gamma                90
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_cell_length_a                   9.1014(5)
_cell_length_b                   5.8581(4)
_cell_length_c                   23.9958(12)
_cell_measurement_reflns_used    1685
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      28.4832
_cell_measurement_theta_min      3.2316
_cell_volume                     1273.29(13)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 15.9784
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_details
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  1 omega  -76.00   -8.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2889  -77.0000  150.0000 68

  2 omega  -76.00  -39.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2889 -178.0000    0.0000 37

  3 omega   41.00   90.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3827   57.0000   30.0000 49

  4 omega  -44.00   38.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3827  -77.0000 -120.0000 82

  5 omega  -12.00   74.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3827   77.0000  -90.0000 86
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0657345000
_diffrn_orient_matrix_UB_12      0.0164835000
_diffrn_orient_matrix_UB_13      -0.0180073000
_diffrn_orient_matrix_UB_21      0.0420098000
_diffrn_orient_matrix_UB_22      0.0449639000
_diffrn_orient_matrix_UB_23      -0.0208712000
_diffrn_orient_matrix_UB_31      0.0072256000
_diffrn_orient_matrix_UB_32      -0.1111014000
_diffrn_orient_matrix_UB_33      -0.0110957000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            7291
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.543
_diffrn_reflns_theta_min         3.412
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2937
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0946
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0435P)^2^+0.2488P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1427
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1813
_reflns_number_total             2937
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01410_si_002.cif
_cod_data_source_block           0927-whs-90-xds
_cod_database_code               4032693
_shelxl_version_number           2014-3
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H3(0.048) H1(0.056) H16(0.058) H6(0.07) H10A(0.058) H10B(0.058)
 H9(0.061) H12(0.065) H14(0.074) H7(0.084) H8(0.079) H15(0.071) H13(0.077)
 Fixed X: H3(-0.0601) H1(-0.1057) H16(-0.3277) H6(0.3338) H10A(-0.2166) H10B(-
 0.1253) H9(0.0596) H12(-0.3657) H14(-0.6655) H7(0.3546) H8(0.2172) H15(-
 0.5391) H13(-0.5805)
 Fixed Y: H3(0.5853) H1(0.1855) H16(0.2321) H6(0.0497) H10A(0.4919)
 H10B(0.6367) H9(0.7175) H12(0.8544) H14(0.6349) H7(0.3135) H8(0.6454)
 H15(0.2966) H13(0.9117)
 Fixed Z: H3(0.1307) H1(0.0234) H16(0.0965) H6(0.2395) H10A(-0.012)
 H10B(0.0339) H9(0.2257) H12(0.0288) H14(0.1268) H7(0.3114) H8(0.3041)
 H15(0.1403) H13(0.0707)
;
_olex2_submission_special_instructions 'No special instructions were received'