#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:07:09 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180375 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/44/7204408.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7204408
loop_
_publ_author_name
'Correa, Waldo H.'
'Papadopoulos, Stavroula'
'Radnidge, Peta'
'Roberts, Brett A.'
'Scott, Janet L.'
_publ_section_title
;
 Direct, efficient, solvent-free synthesis of
 2-aryl-1,2,3,4-tetrahydroquinazolines
;
_journal_issue                   3
_journal_name_full               'Green Chemistry'
_journal_page_first              245
_journal_paper_doi               10.1039/b202729c
_journal_volume                  4
_journal_year                    2002
_chemical_formula_sum            'C14 H14 N2'
_chemical_formula_weight         210.27
_chemical_melting_point          372.9(17)
_chemical_name_common            2-phenyl-1,2,3,4-tetrahydroquinazoline
_chemical_name_systematic
;
2-phenyl-1,2,3,4-tetrahydroquinazoline
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.837(2)
_cell_angle_beta                 98.858(2)
_cell_angle_gamma                101.754(4)
_cell_formula_units_Z            4
_cell_length_a                   9.4360(5)
_cell_length_b                   10.4454(5)
_cell_length_c                   12.0165(8)
_cell_measurement_temperature    123(2)
_cell_volume                     1120.40(11)
_computing_cell_refinement       'Nonius Collect'
_computing_data_collection       'Nonius Collect'
_computing_data_reduction        'Nonius Collect'
_computing_molecular_graphics    Xseed
_computing_publication_material  Ciftab
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.810
_diffrn_measured_fraction_theta_max 0.810
_diffrn_measurement_device_type  'Enraf Nonius Kappa CCD'
_diffrn_measurement_method       'φ + w scans'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0926
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6463
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            beige
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prisms
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4502
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1408
_refine_ls_R_factor_gt           0.0822
_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/[σ²(Fo²)+(0.1415P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2063
_refine_ls_wR_factor_ref         0.2397
_reflns_number_gt                2658
_reflns_number_total             4502
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b202729c.txt
_cod_data_source_block           4a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/adriana/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_enum 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value '98.1-101.5 deg. C' was changed to
'372.9(17)' - it was converted from degrees Celsius(C) to Kelvins(K),
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7204408
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.2475(3) 0.5094(2) 0.9274(2) 0.0253(6) Uani 1 1 d D . .
C15 C 0.1406(3) 0.2931(3) 0.6365(2) 0.0250(7) Uani 1 1 d . . .
H15 H 0.1157 0.2008 0.6011 0.030 Uiso 1 1 calc R . .
C18 C 0.2151(3) 0.5621(3) 0.7382(2) 0.0237(7) Uani 1 1 d . . .
H18 H 0.2415 0.6547 0.7726 0.028 Uiso 1 1 calc R . .
C110 C 0.1744(3) 0.3306(3) 0.7560(2) 0.0233(6) Uani 1 1 d . . .
C16' C 0.1480(3) 0.4691(3) 1.1886(3) 0.0260(7) Uani 1 1 d . . .
H16' H 0.0460 0.4368 1.1552 0.031 Uiso 1 1 calc R . .
C19 C 0.2113(3) 0.4682(3) 0.8075(2) 0.0204(6) Uani 1 1 d . . .
C13' C 0.4445(3) 0.5598(3) 1.2877(3) 0.0298(7) Uani 1 1 d . . .
H13' H 0.5464 0.5893 1.3217 0.036 Uiso 1 1 calc R . .
C11' C 0.2516(3) 0.4639(3) 1.1198(2) 0.0253(7) Uani 1 1 d . . .
N13 N 0.2456(3) 0.2873(3) 0.9544(2) 0.0431(8) Uani 1 1 d . . .
C15' C 0.1907(3) 0.5206(3) 1.3055(3) 0.0294(7) Uani 1 1 d . . .
H15' H 0.1180 0.5248 1.3518 0.035 Uiso 1 1 calc R . .
C14' C 0.3385(3) 0.5662(3) 1.3556(3) 0.0283(7) Uani 1 1 d . . .
H14' H 0.3676 0.6018 1.4361 0.034 Uiso 1 1 calc R . .
C14 C 0.1786(4) 0.2290(3) 0.8312(3) 0.0335(8) Uani 1 1 d . . .
H14A H 0.0765 0.1776 0.8261 0.040 Uiso 1 1 calc R . .
H14B H 0.2351 0.1655 0.8007 0.040 Uiso 1 1 calc R . .
C12' C 0.4006(3) 0.5098(3) 1.1697(3) 0.0286(7) Uani 1 1 d . . .
H12' H 0.4728 0.5070 1.1228 0.034 Uiso 1 1 calc R . .
C17 C 0.1810(3) 0.5219(3) 0.6199(2) 0.0245(7) Uani 1 1 d . . .
H17 H 0.1838 0.5872 0.5736 0.029 Uiso 1 1 calc R . .
C16 C 0.1423(3) 0.3866(3) 0.5676(2) 0.0254(7) Uani 1 1 d . . .
H16 H 0.1175 0.3591 0.4861 0.030 Uiso 1 1 calc R . .
C12 C 0.2009(4) 0.4086(3) 0.9916(3) 0.0335(8) Uani 1 1 d . . .
H12 H 0.0906 0.3859 0.9756 0.040 Uiso 1 1 calc R . .
N21 N 0.2824(3) 0.0450(2) 0.0762(2) 0.0262(6) Uani 1 1 d D . .
C29 C 0.3051(3) 0.0611(3) 0.1961(2) 0.0202(6) Uani 1 1 d . . .
C21' C 0.1936(3) -0.0920(3) -0.1174(2) 0.0254(7) Uani 1 1 d . . .
C26' C 0.0560(3) -0.1184(3) -0.1872(3) 0.0271(7) Uani 1 1 d . . .
H26' H -0.0296 -0.1341 -0.1543 0.033 Uiso 1 1 calc R . .
C23' C 0.3038(3) -0.0779(3) -0.2855(3) 0.0293(7) Uani 1 1 d . . .
H23' H 0.3889 -0.0651 -0.3193 0.035 Uiso 1 1 calc R . .
C25' C 0.0408(3) -0.1222(3) -0.3033(3) 0.0284(7) Uani 1 1 d . . .
H25' H -0.0548 -0.1381 -0.3494 0.034 Uiso 1 1 calc R . .
C210 C 0.2948(3) -0.0512(3) 0.2462(2) 0.0233(6) Uani 1 1 d . . .
C22' C 0.3185(3) -0.0713(3) -0.1675(3) 0.0296(7) Uani 1 1 d . . .
H22' H 0.4141 -0.0526 -0.1207 0.036 Uiso 1 1 calc R . .
C28 C 0.3433(3) 0.1890(3) 0.2656(2) 0.0243(7) Uani 1 1 d . . .
H28 H 0.3527 0.2652 0.2315 0.029 Uiso 1 1 calc R . .
N23 N 0.2670(3) -0.1900(3) 0.0482(2) 0.0449(8) Uani 1 1 d . . .
C26 C 0.3567(3) 0.0946(3) 0.4356(3) 0.0283(7) Uani 1 1 d . . .
H26 H 0.3740 0.1060 0.5170 0.034 Uiso 1 1 calc R . .
C25 C 0.3204(3) -0.0319(3) 0.3660(3) 0.0278(7) Uani 1 1 d . . .
H25 H 0.3128 -0.1076 0.4007 0.033 Uiso 1 1 calc R . .
C24' C 0.1638(3) -0.1033(3) -0.3538(3) 0.0271(7) Uani 1 1 d . . .
H24' H 0.1527 -0.1075 -0.4344 0.033 Uiso 1 1 calc R . .
C27 C 0.3673(3) 0.2051(3) 0.3838(3) 0.0273(7) Uani 1 1 d . . .
H27 H 0.3915 0.2925 0.4306 0.033 Uiso 1 1 calc R . .
C24 C 0.2614(4) -0.1898(3) 0.1702(3) 0.0346(8) Uani 1 1 d . . .
H24A H 0.3332 -0.2386 0.2005 0.042 Uiso 1 1 calc R . .
H24B H 0.1618 -0.2390 0.1750 0.042 Uiso 1 1 calc R . .
C22 C 0.2054(4) -0.0864(3) 0.0107(3) 0.0344(8) Uani 1 1 d . . .
H22 H 0.1024 -0.1017 0.0253 0.041 Uiso 1 1 calc R . .
H11N H 0.250(3) 0.604(2) 0.960(3) 0.041(9) Uiso 1 1 d D . .
H21N H 0.266(4) 0.124(3) 0.046(3) 0.063(12) Uiso 1 1 d D . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 N11 C12 115.8(2) . . ?
C16 C15 C110 121.8(3) . . ?
C17 C18 C19 120.6(3) . . ?
C15 C110 C19 118.5(3) . . ?
C15 C110 C14 121.9(2) . . ?
C19 C110 C14 119.5(3) . . ?
C11' C16' C15' 120.7(3) . . ?
C18 C19 N11 120.4(2) . . ?
C18 C19 C110 119.6(3) . . ?
N11 C19 C110 120.0(3) . . ?
C14' C13' C12' 119.7(3) . . ?
C16' C11' C12' 119.2(3) . . ?
C16' C11' C12 119.4(3) . . ?
C12' C11' C12 121.4(3) . . ?
C12 N13 C14 110.3(2) . . ?
C16' C15' C14' 120.4(3) . . ?
C15' C14' C13' 119.6(3) . . ?
N13 C14 C110 114.4(2) . . ?
C13' C12' C11' 120.4(3) . . ?
C18 C17 C16 120.7(3) . . ?
C15 C16 C17 118.8(3) . . ?
N13 C12 N11 112.3(3) . . ?
N13 C12 C11' 112.6(3) . . ?
N11 C12 C11' 110.7(2) . . ?
C29 N21 C22 116.1(2) . . ?
C28 C29 N21 120.0(3) . . ?
C28 C29 C210 120.1(3) . . ?
N21 C29 C210 119.9(2) . . ?
C26' C21' C22' 118.6(3) . . ?
C26' C21' C22 119.4(3) . . ?
C22' C21' C22 121.9(3) . . ?
C25' C26' C21' 121.2(3) . . ?
C22' C23' C24' 119.7(3) . . ?
C26' C25' C24' 120.5(3) . . ?
C25 C210 C29 118.6(3) . . ?
C25 C210 C24 121.5(3) . . ?
C29 C210 C24 119.8(3) . . ?
C23' C22' C21' 120.5(3) . . ?
C27 C28 C29 120.1(3) . . ?
C22 N23 C24 111.0(2) . . ?
C25 C26 C27 118.7(3) . . ?
C26 C25 C210 121.7(3) . . ?
C25' C24' C23' 119.4(3) . . ?
C28 C27 C26 120.8(3) . . ?
N23 C24 C210 114.1(2) . . ?
N23 C22 N21 112.6(3) . . ?
N23 C22 C21' 112.9(2) . . ?
N21 C22 C21' 110.8(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N11 C19 1.398(3) . ?
N11 C12 1.446(4) . ?
C15 C16 1.383(4) . ?
C15 C110 1.391(4) . ?
C18 C17 1.378(4) . ?
C18 C19 1.389(4) . ?
C110 C19 1.413(4) . ?
C110 C14 1.509(4) . ?
C16' C11' 1.377(4) . ?
C16' C15' 1.380(4) . ?
C13' C14' 1.390(4) . ?
C13' C12' 1.390(4) . ?
C11' C12' 1.391(4) . ?
C11' C12 1.514(4) . ?
N13 C12 1.437(4) . ?
N13 C14 1.485(4) . ?
C15' C14' 1.381(4) . ?
C17 C16 1.393(4) . ?
N21 C29 1.399(4) . ?
N21 C22 1.442(4) . ?
C29 C28 1.394(4) . ?
C29 C210 1.400(4) . ?
C21' C26' 1.380(4) . ?
C21' C22' 1.399(4) . ?
C21' C22 1.516(4) . ?
C26' C25' 1.374(4) . ?
C23' C22' 1.391(4) . ?
C23' C24' 1.392(4) . ?
C25' C24' 1.385(4) . ?
C210 C25 1.395(4) . ?
C210 C24 1.517(4) . ?
C28 C27 1.378(4) . ?
N23 C22 1.432(4) . ?
N23 C24 1.475(4) . ?
C26 C25 1.383(4) . ?
C26 C27 1.395(4) . ?
