Synthesis of substituted chromanones: an organocatalytic aldol/oxa-Michael reaction.
Butler, Jeffrey D.; Conrad, Wayne E.; Lodewyk, Michael W.; Fettinger, James C.; Tantillo, Dean J.; Kurth, Mark J.; Organic letters 12 (2010) 3410–3413; doi:10.1021/ol101221c

data_1503078
_publ_section_title
;
 Synthesis of substituted chromanones: an organocatalytic
 aldol/oxa-Michael reaction.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3410
_journal_page_last               3413
_journal_paper_doi               10.1021/ol101221c
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C14 H16 O2'
_chemical_formula_sum            'C14 H16 O2'
_chemical_formula_weight         216.27
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 104.9280(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.6103(4)
_cell_length_b                   9.3464(3)
_cell_length_c                   21.5764(8)
_cell_measurement_reflns_used    9988
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      68.21
_cell_measurement_theta_min      3.96
_cell_volume                     2262.33(14)
_computing_cell_refinement       'SAINT (7.68A) (Bruker, 2008)'
_computing_data_collection       'Apex2 (2010-1) (Bruker, 2010)'
_computing_data_reduction        'SAINT (7.68A) (Bruker, 2008)'
_computing_molecular_graphics    'SHELXTL 5.1, XP (Sheldrick, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker APEX-II DUO CCD'
_diffrn_measurement_method       '\f and \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  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8716
_diffrn_reflns_theta_full        68.49
_diffrn_reflns_theta_max         68.49
_diffrn_reflns_theta_min         3.96
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  0.9650
_exptl_absorpt_correction_T_min  0.8495
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS 2008/2 (Sheldrick, 2008)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.00081(18)
_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   1.035
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     412
_refine_ls_number_reflns         4014
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0470P)^2^+0.8370P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0937
_reflns_number_gt                3754
_reflns_number_total             4014
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101221c_si_001.cif
_cod_data_source_block           jf1930fmi
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Numerical'
changed to 'numerical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1503078