Novel isocyanide-based four-component reaction: a facile synthesis of fully substituted 3,4-dihydrocoumarin derivatives.
Shaabani, Ahmad; Soleimani, Ebrahim; Rezayan, Ali Hossein; Sarvary, Afshin; Khavasi, Hamid Reza; Organic letters 10 (2008) 2581–2584; doi:10.1021/ol800856e

data_1504712
_publ_section_title
;
 Novel isocyanide-based four-component reaction: a facile synthesis of
 fully substituted 3,4-dihydrocoumarin derivatives.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2581
_journal_page_last               2584
_journal_paper_doi               10.1021/ol800856e
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C17 H21 N1 O5'
_chemical_formula_sum            'C17 H21 N O5'
_chemical_formula_weight         319.35
_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                   9.7437(6)
_cell_length_b                   9.9574(5)
_cell_length_c                   17.4514(12)
_cell_measurement_reflns_used    3458
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      29.8
_cell_measurement_theta_min      2.33
_cell_volume                     1693.17(18)
_computing_cell_refinement       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_collection       'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_data_reduction        'X-Area 1.31 (Stoe & Cie GmbH, 2005)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'STOE IPDS II'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0785
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_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13705
_diffrn_reflns_theta_full        29.28
_diffrn_reflns_theta_max         29.28
_diffrn_reflns_theta_min         2.33
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'shape of crystal determined optically'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(1)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.232
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2602
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.232
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0572
_refine_ls_shift/su_max          0.082
_refine_ls_shift/su_mean         0.073
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0304P)^2^+0.7121P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1145
_reflns_number_gt                2284
_reflns_number_total             2602
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol800856e-file003.cif
_cod_data_source_block           kh262
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P212121
_cod_original_formula_sum        'C17 H21 N1 O5'
_cod_database_code               1504712