Swift and Efficient Synthesis of 4-Phenylquinazolines: Involvement of N-Heterocyclic Carbene in the Key Cyclization Step
Julien Debray; Jean-Marc Lévêque; Christian Philouze; Micheline Draye; Martine Demeunynck; Journal of Organic Chemistry 75 (2010) 2092–2095; doi:10.1021/jo902726k

data_4025316
_publ_section_title
;
 Swift and Efficient Synthesis of 4-Phenylquinazolines: Involvement of
 N-Heterocyclic Carbene in the Key Cyclization Step
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2092
_journal_page_last               2095
_journal_paper_doi               10.1021/jo902726k
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C20 H18 N4 '
_chemical_formula_sum            'C20 H18 N4'
_chemical_formula_weight         314.39
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_date             2009-07-30
_audit_creation_method           'by teXsan v1.8'
_audit_update_record
;
?
;
_cell_angle_alpha                107.39(4)
_cell_angle_beta                 102.58(7)
_cell_angle_gamma                108.01(4)
_cell_formula_units_Z            2
_cell_length_a                   8.770(6)
_cell_length_b                   10.038(4)
_cell_length_c                   10.810(5)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293.0
_cell_measurement_theta_max      0.0
_cell_measurement_theta_min      0.0
_cell_volume                     811.6(9)
_computing_cell_refinement       'Bruker-Enraf-Nonius CAD4'
_computing_data_collection       'Bruker-Enraf-Nonius CAD4'
_computing_data_reduction        'teXsan (MSC, 1992-1997)'
_computing_publication_material  'teXsan (MSC, 1992-1997)'
_computing_structure_refinement  'teXsan (MSC, 1992-1997)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      293.0
_diffrn_measurement_device_type  CAD-4
_diffrn_measurement_method       \w
_diffrn_orient_matrix_UB_11      0.03977
_diffrn_orient_matrix_UB_12      -0.06662
_diffrn_orient_matrix_UB_13      0.03938
_diffrn_orient_matrix_UB_21      -0.10580
_diffrn_orient_matrix_UB_22      -0.09064
_diffrn_orient_matrix_UB_23      -0.06612
_diffrn_orient_matrix_UB_31      0.05918
_diffrn_orient_matrix_UB_32      -0.01850
_diffrn_orient_matrix_UB_33      -0.06868
_diffrn_radiation_detector       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.04082
_diffrn_reflns_av_sigmaI/netI    0.090
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3397
_diffrn_reflns_reduction_process 'Lp corrections applied'
_diffrn_reflns_theta_max         74.89
_diffrn_reflns_theta_min         4.56
_diffrn_standards_decay_%        9.01
_diffrn_standards_interval_count 120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.617
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light orange'
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_description       platelet
_exptl_crystal_F_000             332.00
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.24
_refine_ls_extinction_coef       0.000005(2)
_refine_ls_extinction_expression 'equ(3) Acta Cryst.(1968) A24, p213.'
_refine_ls_extinction_method     'Zachariasen (1967)'
_refine_ls_goodness_of_fit_all   1.988
_refine_ls_goodness_of_fit_ref   1.988
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     218
_refine_ls_number_reflns         1682
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0649
_refine_ls_shift/su_max          0.0012
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[\s^2^(Fo) + 0.00051|Fo|^2^]'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.0775
_refine_ls_wR_factor_ref         0.0775
_reflns_number_gt                1682
_reflns_number_total             3215
_reflns_threshold_expression     I>2.00\s(I)
_cod_data_source_file            jo902726k_si_002.cif
_cod_data_source_block           DEBRA
_cod_depositor_comments
;
 Changing the values of the '_atom_site_label' and '_atom_site_aniso_label'
 to match those of related data items (e. g. '_geom_angle_atom_site_label_*').

 Antanas Vaitkus,
 2017-03-03

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 

The following automatic conversions were performed:
data name '_geom_bond_atom_site_label_D' replaced with
'_geom_hbond_atom_site_label_D' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_bond_atom_site_label_H' replaced with
'_geom_hbond_atom_site_label_H' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_contact_atom_site_label_a' replaced with
'_geom_hbond_atom_site_label_A' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_bond_distance_DH' replaced with '_geom_hbond_distance_DH'
as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_contact_distance_HA' replaced with
'_geom_hbond_distance_HA' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_contact_distance_DA' replaced with
'_geom_hbond_distance_DA' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_angle_DHA' replaced with '_geom_hbond_angle_DHA' as
specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

data
name '_geom_contact_site_symmetry_A' replaced with
'_geom_hbond_site_symmetry_A' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 5005 2017-03-03 11:38:54Z antanas 
;
_cod_original_cell_volume        812(1)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C20 H18 N4 '
_cod_database_code               4025316