Enantioselective synthesis of 4H-pyranonaphthoquinones via sequential squaramide and silver catalysis.
Kaya, Uğur; Chauhan, Pankaj; Hack, Daniel; Deckers, Kristina; Puttreddy, Rakesh; Rissanen, Kari; Enders, Dieter; Chemical communications (Cambridge, England) 52 (2016) 1669–1672; doi:10.1039/c5cc09592a

data_7118558
_publ_section_title
;
 Enantioselective synthesis of 4H-pyranonaphthoquinones via sequential
 squaramide and silver catalysis.
;
_journal_issue                   8
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1669
_journal_page_last               1672
_journal_paper_doi               10.1039/c5cc09592a
_journal_volume                  52
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H12 Br N O5'
_chemical_formula_sum            'C20 H12 Br N O5'
_chemical_formula_weight         426.22
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-11-05
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2015-11-18 deposited with the CCDC.
2015-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.25660(5)
_cell_length_b                   12.33003(13)
_cell_length_c                   25.5995(3)
_cell_measurement_reflns_used    15355
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      74.1650
_cell_measurement_theta_min      3.9780
_cell_volume                     1659.21(3)
_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      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -46.00   18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000    0.0000 64

  2 omega  -49.00  -20.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000  -30.0000 29

  3 omega  -69.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   57.0000 -150.0000 99

  4 omega   89.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   77.0000  -90.0000 27

  5 omega   78.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000    0.0000 31

  6 omega  113.00  177.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000  -30.0000 64

  7 omega  152.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000    0.0000 26

  8 omega  139.00  165.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000  -90.0000 26

  9 omega  153.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   69.0000 -154.9633 25

 10 omega  133.00  170.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   59.0000   13.7630 37

 11 omega  133.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   63.0000   74.9322 45

 12 omega  133.00  159.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000  120.0000 26

 13 omega  121.00  176.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000   60.0000 55

 14 omega  109.00  173.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000  150.0000 64

 15 omega   74.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000  150.0000 26

 16 omega   78.00  110.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000  120.0000 32

 17 omega   77.00  103.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   63.0000   74.9322 26

 18 omega   76.00  164.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   69.0000   34.6403 88

 19 omega   79.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000 -120.0000 27

 20 omega   78.00  105.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000  -90.0000 27

 21 omega   80.00  144.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000  -60.0000 64

 22 omega   86.00  112.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000 -180.0000 26

 23 omega   77.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   69.0000 -154.9633 27

 24 omega   82.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   45.0000 -180.0000 25

 25 omega   79.00  170.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   56.0000 -158.0661 91

 26 omega  112.00  139.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -77.0000   30.0000 27

 27 omega   57.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -94.0000   90.0000 50

 28 omega   41.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -77.0000   30.0000 63

 29 omega   54.00  122.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601 -125.0000  -60.0000 68

 30 omega   33.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -94.0000  -30.0000 74

 31 omega   25.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601  -94.0000 -180.0000 75

 32 omega   78.00  105.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000   30.0000 27

 33 omega   78.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000   60.0000 26

 34 omega   78.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000   90.0000 26

 35 omega   74.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000   90.0000 26

 36 omega   74.00  130.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000  120.0000 56

 37 omega   78.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   59.0000   13.7630 26

 38 omega   78.00  117.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000  -30.0000 39

 39 omega   74.00  145.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000  -60.0000 71

 40 omega   78.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   61.0000 -150.0000 26

 41 omega   74.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000 -150.0000 26

 42 omega   74.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000 -120.0000 104

 43 omega   74.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000  -90.0000 26

 44 omega   74.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000  -30.0000 26

 45 omega   75.00  100.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6601   77.0000    0.0000 25

 46 omega    9.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   77.0000  120.0000 69

 47 omega   13.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   77.0000  -90.0000 26

 48 omega    9.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   77.0000 -180.0000 108

 49 omega    2.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013  -99.0000   60.0000 72

 50 omega  -76.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -57.0000   60.0000 62

 51 omega  -95.00   -9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -77.0000    0.0000 86

 52 omega -109.00  -84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -57.0000   60.0000 25

 53 omega -116.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -77.0000  -90.0000 105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.2480526000
_diffrn_orient_matrix_UB_12      0.0646112000
_diffrn_orient_matrix_UB_13      0.0075730000
_diffrn_orient_matrix_UB_21      0.1189666000
_diffrn_orient_matrix_UB_22      -0.0594197000
_diffrn_orient_matrix_UB_23      -0.0469878000
_diffrn_orient_matrix_UB_31      -0.1006768000
_diffrn_orient_matrix_UB_32      0.0889293000
_diffrn_orient_matrix_UB_33      -0.0368612000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            24576
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.750
_diffrn_reflns_theta_max         66.713
_diffrn_reflns_theta_min         3.453
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.688
_exptl_absorpt_correction_T_max  0.851
_exptl_absorpt_correction_T_min  0.372
_exptl_absorpt_correction_type   gaussian
_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)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
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    1.706
_exptl_crystal_description       plate
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.3667
_exptl_crystal_size_mid          0.0463
_exptl_crystal_size_min          0.0403
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1123 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.046(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2936
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0224
_refine_ls_R_factor_gt           0.0206
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0266P)^2^+0.5878P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0523
_refine_ls_wR_factor_ref         0.0537
_reflns_Friedel_coverage         0.684
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2801
_reflns_number_total             2936
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc09592a2.cif
_cod_data_source_block           4e
_cod_database_code               7118558
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C10 H10 N1 O1 Br1'
_reflns_odcompleteness_completeness 99.94
_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
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C17(H17), C18(H18), C19(H19), C20(H20)
;
_shelx_res_checksum              78975
_shelx_hkl_checksum              37412
_olex2_submission_special_instructions 'No special instructions were received'