Quinine-catalyzed highly enantioselective cycloannulation of o-quinone methides with malononitrile.
Adili, Alafate; Tao, Zhong-Lin; Chen, Dian-Feng; Han, Zhi-Yong; Organic & biomolecular chemistry 13 (2015) 2247–2250; doi:10.1039/c4ob02602k

data_7154276
_publ_section_title
;
 Quinine-catalyzed highly enantioselective cycloannulation of o-quinone
 methides with malononitrile.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2247
_journal_page_last               2250
_journal_paper_doi               10.1039/c4ob02602k
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20.5 H17 Cl N2 O4'
_chemical_formula_weight         390.81
_chemical_name_systematic
(S,E)-6-amino-8-(4-methoxystyryl)-8H-[1,3]dioxolo[4,5-g]chromene-7-carbonitrile
_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-2013
_audit_update_record
;
2014-12-14 deposited with the CCDC.
2015-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.948(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.9112(5)
_cell_length_b                   4.5568(2)
_cell_length_c                   21.2328(6)
_cell_measurement_reflns_used    7501
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      69.3425
_cell_measurement_theta_min      3.2748
_cell_volume                     1907.97(11)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            18419
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.469
_diffrn_reflns_theta_min         3.277
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.024
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       needle
_exptl_crystal_F_000             812
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM/Hexanes'
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.270
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 2011 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.040(13)
_refine_ls_extinction_coef       0.0027(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     515
_refine_ls_number_reflns         6653
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0811P)^2^+0.3253P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1371
_refine_ls_wR_factor_ref         0.1466
_reflns_Friedel_coverage         0.644
_reflns_Friedel_fraction_full    0.857
_reflns_Friedel_fraction_max     0.837
_reflns_number_gt                5714
_reflns_number_total             6653
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4ob02602k2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
      Adding full bibliography for 7154276.cif.

2017-03-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum        'C41 H34 Cl2 N4 O8'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     781.62
_cod_database_code               7154276
_shelx_estimated_absorpt_t_min   0.573
_shelx_estimated_absorpt_t_max   0.611
_shelxl_version_number           2013-4
_shelx_res_checksum              21257
_shelx_hkl_checksum              65853