A Regioselective Approach to Trisubstituted 2 (or 6)-Arylaminopyrimidine-5-carbaldehydes and Their Application in the Synthesis of Structurally and Electronically Unique G-C Base Precursors
Rachel L. Beingessner; Bo-Liang Deng; Phillip E. Fanwick; Hicham Fenniri; Journal of Organic Chemistry 73 (2008) 931–939; doi:10.1021/jo7021422

data_4023233
_publ_contact_author_address
;    Department of Chemistry
     Purdue University
     560 Oval Drive 
     West Lafayette, IN 47907-2084
     USA
;
_publ_contact_author_email       fanwick@.xray.chem.purdue.edu
_publ_contact_author_fax         1(765)4940239
_publ_contact_author_name        'Phillip E. Fanwick'
_publ_contact_author_phone       1(765)4944572
_publ_section_title
;
 A Regioselective Approach to Trisubstituted
 2 (or 6)-Arylaminopyrimidine-5-carbaldehydes and Their Application in
 the Synthesis of Structurally and Electronically Unique
 G-C Base Precursors
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              931
_journal_page_last               939
_journal_paper_doi               10.1021/jo7021422
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C11 H6 Cl2 I N3 O'
_chemical_formula_weight         394.00
_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_type_scat_source
'International Tables for Crystallography (Vol C)'
_audit_creation_date             15-05-01
_audit_creation_method           from_MolEN_and_SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 98.1033(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   7.11770(10)
_cell_length_b                   24.8135(5)
_cell_length_c                   21.9306(5)
_cell_measurement_reflns_used    27051
_cell_measurement_temperature    149
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     3834.6(2)
_computing_cell_refinement       DENZO/SCALEPACK_(Otwinowski,_1996)"
_computing_data_collection       Collect_(Nonius,_1998)"
_computing_data_reduction        DENZO/SCALEPACK_(Otwinowski,_1996)"
_computing_molecular_graphics
;
ORTEP (Johnson, 1976)
PLUTON (Spek, 1991)
;
_computing_publication_material  CIF_VAX_MolEN_(Fair,_1990)
_computing_structure_refinement  SHELX97_(Sheldrick,_1997)"
_computing_structure_solution    Direct_methods_(Shelxs97,_Sheldrick,_1997)"
_diffrn_ambient_temperature      149
_diffrn_measured_fraction_theta_max 0.9620
_diffrn_measurement_device_type  Nonius_KappaCCD
_diffrn_radiation_type           MO-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.044
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            27051
_diffrn_reflns_theta_full        23.0
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         5.00
_exptl_absorpt_coefficient_mu    2.889
_exptl_absorpt_correction_T_max  0.6969
_exptl_absorpt_correction_T_min  0.4510
_exptl_absorpt_correction_type   refined_empirical_(Otwinowski_&_Minor,_1996)
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.05
_exptl_crystal_description       needle
_exptl_crystal_F_000             2256
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.70
_refine_diff_density_min         -0.96
_refine_ls_d_res_high            0.81
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment
;
Chemically significant hydrogens refined isotropically
Others riding
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     499
_refine_ls_number_reflns         7330
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.035
_refine_ls_shift/su_max          0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'1/[\s^2^(Fo^2^)+(0.0279P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3  '
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.069
_reflns_number_gt                6430
_reflns_number_total             8438
_reflns_threshold_expression     >2.0\s(I)
_cod_data_source_file            jo7021422-File003.cif
_cod_data_source_block           D58-1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_refine_ls_weighting_scheme' value 'calc ' changed to 'calc' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

'_geom_bond_publ_flag'
value 'YES' changed to 'yes' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (60
times).

'_geom_bond_publ_flag' value 'NO' changed to 'no' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (6
times).

'_geom_angle_publ_flag' value 'YES' changed to 'yes' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (84
times).

'_geom_angle_publ_flag' value 'NO' changed to 'no' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (3 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C11 H6 Cl2 I1 N3 O1'
_cod_database_code               4023233