Asymmetric synthesis of 3,4-diaminochroman-2-ones promoted by guanidine and bisguanidium salt.
Dong, Shunxi; Liu, Xiaohua; Zhang, Yulong; Lin, Lili; Feng, Xiaoming; Organic letters 13 (2011) 5060–5063; doi:10.1021/ol2018888

data_1502426
_publ_section_title
;
 Asymmetric synthesis of 3,4-diaminochroman-2-ones promoted by guanidine
 and bisguanidium salt.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5060
_journal_page_last               5063
_journal_paper_doi               10.1021/ol2018888
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H24 N2 O3'
_chemical_formula_sum            'C29 H24 N2 O3'
_chemical_formula_weight         448.50
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.190(2)
_cell_length_b                   13.078(3)
_cell_length_c                   16.013(3)
_cell_measurement_reflns_used    14711
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.24
_cell_measurement_theta_min      4.36
_cell_volume                     2343.4(8)
_computing_cell_refinement       'Rapid Auto(Rigaku 2001)'
_computing_data_collection       'Rapid Auto(Rigaku 2001)'
_computing_data_reduction        'Rapid Auto(Rigaku 2001)'
_computing_molecular_graphics
;     
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku raxis Rapid IP Area Detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14653
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         4.36
_exptl_absorpt_coefficient_mu    0.662
_exptl_absorpt_correction_T_max  0.7482
_exptl_absorpt_correction_T_min  0.6905
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS by T. Higashi, June 3, 2003'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.51
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.3(2)
_refine_ls_extinction_coef       0.0075(3)
_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   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4196
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0309P)^2^+0.4530P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0794
_reflns_number_gt                3929
_reflns_number_total             4196
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2018888_si_003.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1502426