Asymmetric Synthesis of Functionalized Tricyclic Chromanes via an Organocatalytic Triple Domino Reaction.
Kumar, Mukesh; Chauhan, Pankaj; Valkonen, Arto; Rissanen, Kari; Enders, Dieter; Organic letters 19 (2017) 3025–3028; doi:10.1021/acs.orglett.7b01322

data_1546096
_publ_section_title
;
 Asymmetric Synthesis of Functionalized Tricyclic Chromanes via an
 Organocatalytic Triple Domino Reaction.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              3025
_journal_page_last               3028
_journal_paper_doi               10.1021/acs.orglett.7b01322
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H19 N O4'
_chemical_formula_sum            'C21 H19 N O4'
_chemical_formula_weight         349.37
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 105.938(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.3201(2)
_cell_length_b                   7.3604(2)
_cell_length_c                   14.5839(3)
_cell_measurement_reflns_used    4852
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      73.7310
_cell_measurement_theta_min      5.5170
_cell_volume                     858.78(4)
_computing_cell_refinement       CrysAlisPro
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        CrysAlisPro
_computing_molecular_graphics    SHELXL-2014/7
_computing_publication_material  SHELXL-2014/7
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2014 (Burla, et al., 2014)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 5.1977
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7209
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.461
_diffrn_reflns_theta_min         5.530
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.766
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       prism
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1311 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3288
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0310
_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^)+(0.0363P)^2^+0.0823P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0750
_refine_ls_wR_factor_ref         0.0766
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_full    0.939
_reflns_Friedel_fraction_max     0.883
_reflns_number_gt                3149
_reflns_number_total             3288
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01322_si_001.cif
_cod_data_source_block           5a
_cod_depositor_comments          'Adding full bibliography for 1546096.cif.'
_cod_database_code               1546096
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.887
_shelx_estimated_absorpt_t_max   0.948
_shelx_res_checksum              34249
_shelx_hkl_checksum              91623