4-metalated condensed pyrimidines: their preparation and reaction with aldehydes under Barbier-type conditions.
Therkelsen, Frans D.; Rottländer, Mario; Thorup, Niels; Pedersen, Erik Bjerregaard; Organic letters 6 (2004) 1991–1994; doi:10.1021/ol049432v

data_1507089
_publ_section_title
;
 4-metalated condensed pyrimidines: their preparation and reaction with
 aldehydes under Barbier-type conditions.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              1991
_journal_page_last               1994
_journal_paper_doi               10.1021/ol049432v
_journal_volume                  6
_journal_year                    2004
_chemical_formula_sum            'C20 H16 N2 O2 S'
_chemical_formula_weight         348.41
_chemical_melting_point          437
_chemical_name_systematic
; 
4-Methoxyphenyl-(6-phenylthieno[2,3-d]pyrimidin-4-yl)-methanol 
;
_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           'SHELXTL 6.12 and manual editing'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8532(4)
_cell_length_b                   14.5436(10)
_cell_length_c                   19.3274(14)
_cell_measurement_reflns_used    7950
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.374
_cell_measurement_theta_min      2.531
_cell_volume                     1645.3(2)
_computing_cell_refinement       'SAINT 6.36A (Bruker-AXS, 2000)'
_computing_data_collection       'SMART 5.628 (Bruker-AXS, 2002)'
_computing_data_reduction        'SAINT 6.36A (Bruker-AXS, 2000)'
_computing_molecular_graphics
;
'SHELXTL 6.12 (Bruker-AXS, 2001) and PLATON (Spek, 1990)'
;
_computing_publication_material
;
'SHELXTL 6.12 (Bruker-AXS, 2001) and PLATON (Spek, 1990)' 
;
_computing_structure_refinement  'SHELXTL 6.12 (Bruker-AXS, 2001)'
_computing_structure_solution    'SHELXTL 6.12 (Bruker-AXS, 2001)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART-APEX'
_diffrn_measurement_method       'omega scan, frame data integration'
_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  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16586
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.9708
_exptl_absorpt_correction_T_min  0.9566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS ver 2.03 (Sheldrick 2001)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.720
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3353
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0620P)^2^+0.5789P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.0985
_reflns_number_gt                3206
_reflns_number_total             3353
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol049432vsi20040326_085319.cif
_cod_data_source_block           fdt097ka
_cod_database_code               1507089