Asymmetric synthesis of 3-aminodihydrocoumarins via the chiral guanidine catalyzed cascade reaction of azlactones
Ruan, Sai; Lin, Xiaobin; Xie, Lihua; Lin, Lili; Feng, Xiaoming; Liu, Xiaohua; Organic Chemistry Frontiers 5 (2018) 32–; doi:10.1039/C7QO00768J

data_1553894
_publ_section_title
;
 Asymmetric synthesis of 3-aminodihydrocoumarins via the chiral guanidine
 catalyzed cascade reaction of azlactones
;
_journal_issue                   1
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              32
_journal_paper_doi               10.1039/C7QO00768J
_journal_volume                  5
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H20 N2 O5'
_chemical_formula_sum            'C24 H20 N2 O5'
_chemical_formula_weight         416.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-12-22
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2017-07-05 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.532(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.31419(17)
_cell_length_b                   19.2062(3)
_cell_length_c                   11.0205(2)
_cell_measurement_reflns_used    14401
_cell_measurement_temperature    135
_cell_measurement_theta_max      72.5770
_cell_measurement_theta_min      4.2420
_cell_volume                     2057.49(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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      air
_diffrn_ambient_temperature      135
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9791
_diffrn_measurement_details
;
  1 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   60.0000 84

  2 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000  -60.0000 74

  3 omega    7.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   19.0000    0.0000 101

  4 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000 -150.0000 94

  5 omega  -31.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000    0.0000 94

  6 omega    7.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   19.0000   30.0000 101

  7 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000  120.0000 84

  8 omega  -33.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -38.0000   60.0000 88

  9 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000   30.0000 74

 10 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000  -90.0000 84

 11 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000 -150.0000 74

 12 omega   90.00  175.00   1.0000    2.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -150.0000 85

 13 omega   38.00   91.00   1.0000    2.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

 14 omega   38.00  116.00   1.0000    2.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 78

 15 omega   38.00  116.00   1.0000    2.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 78

 16 omega   40.00  135.00   1.0000    2.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  120.0000 95

 17 omega   37.00  146.00   1.0000    2.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000   90.0000 109

 18 omega   39.00  109.00   1.0000    2.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -90.0000 70

 19 omega   40.00   98.00   1.0000    2.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

 20 omega   38.00   91.00   1.0000    2.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 53

 21 omega   40.00   98.00   1.0000    2.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 58

 22 omega   39.00  109.00   1.0000    2.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 70

 23 omega   40.00   98.00   1.0000    2.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 58

 24 omega   40.00   98.00   1.0000    2.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000    0.0000 58

 25 omega   38.00   91.00   1.0000    2.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

 26 omega   70.00  178.00   1.0000    2.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -30.0000 108

 27 omega   39.00  109.00   1.0000    2.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -30.0000 70

 28 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  -60.0000 94

 29 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000   30.0000 94

 30 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000   60.0000 94

 31 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000 -180.0000 94

 32 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  150.0000 84

 33 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   38.0000  150.0000 88

 34 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  -90.0000 84

 35 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000 -180.0000 84

 36 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000  150.0000 94

 37 omega   20.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   30.0000 84

 38 omega  -31.00   53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000   60.0000 84

 39 omega   70.00  178.00   1.0000    2.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000   60.0000 108

 40 omega   70.00  178.00   1.0000    2.2300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  150.0000 108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0693748000
_diffrn_orient_matrix_UB_12      0.0304330000
_diffrn_orient_matrix_UB_13      0.1356736000
_diffrn_orient_matrix_UB_21      -0.0384746000
_diffrn_orient_matrix_UB_22      0.0739992000
_diffrn_orient_matrix_UB_23      -0.0538378000
_diffrn_orient_matrix_UB_31      -0.1372555000
_diffrn_orient_matrix_UB_32      -0.0054746000
_diffrn_orient_matrix_UB_33      0.0263371000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            30369
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.757
_diffrn_reflns_theta_min         4.549
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.785
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.344
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 3551 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         8035
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0759P)^2^+0.1626P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1097
_reflns_Friedel_coverage         0.918
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                7783
_reflns_number_total             8035
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00768j2.cif
_cod_data_source_block           fxm-ruan2
_cod_depositor_comments
;

2022-05-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        2057.48(6)
_cod_original_formula_moiety     '2(C24 H20 N2 O5)'
_cod_original_formula_sum        'C48 H40 N4 O10'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     832.84
_cod_database_code               1553894
_reflns_odcompleteness_completeness 99.95
_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) groups
2.a Ternary CH refined with riding coordinates:
 C00P(H00P), C00V(H00V)
2.b Secondary CH2 refined with riding coordinates:
 C013(H01I,H01K), C017(H01A,H01B), C019(H01C,H01D), C01B(H01N,H01O)
2.c Aromatic/amide H refined with riding coordinates:
 N00A(H00A), N00B(H00B), C00N(H00N), C00Q(H00Q), C00R(H00R), C00U(H00U),
 C00Y(H00Y), C010(H010), C011(H011), C012(H012), C014(H014), C015(H015),
 C016(H016), C018(H018), C01A(H01E), C01C(H01F), C01D(H01Q), C01E(H01G),
 C01F(H01H), C01G(H01R), C01H(H01S), C01I(H01T), C01J(H01J), C01K(H01U),
 C01L(H01L), C01M(H01M), C01N(H01V), C01O(H01W), C01P(H01P), C01Q(H01X)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-12-22
_olex2_submission_special_instructions 'No special instructions were received'