Asymmetric synthesis of 3,4-dihydrocoumarin motif with an all-carbon quaternary stereocenter via a Michael-acetalization sequence with bifunctional amine-thiourea organocatalysts.
Hong, Bor-Cherng; Kotame, Prakash; Lee, Gene-Hsiang; Organic letters 13 (2011) 5758–5761; doi:10.1021/ol202331j

data_1502529
_publ_section_title
;
 Asymmetric synthesis of 3,4-dihydrocoumarin motif with an all-carbon
 quaternary stereocenter via a Michael-acetalization sequence with
 bifunctional amine-thiourea organocatalysts.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5758
_journal_page_last               5761
_journal_paper_doi               10.1021/ol202331j
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H14 Br N O5'
_chemical_formula_weight         416.22
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
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_cell_angle_alpha                90.00
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_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.3284(9)
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_cell_length_c                   12.3764(9)
_cell_measurement_reflns_used    2655
_cell_measurement_temperature    150(2)
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_cell_volume                     851.04(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'BRUKER SMART APEXCCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
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_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
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_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11296
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_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    2.446
_exptl_absorpt_correction_T_max  0.8283
_exptl_absorpt_correction_T_min  0.4057
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.643
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_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.002(7)
_refine_ls_extinction_method     none
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_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3900
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_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0363
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0310P)^2^+0.1085P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0774
_reflns_number_gt                3550
_reflns_number_total             3900
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_cod_data_source_file            ol202331j_si_002.cif
_cod_data_source_block           ic14818
_cod_depositor_comments
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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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not_measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1502529