#------------------------------------------------------------------------------
#$Date: 2019-11-28 20:36:30 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244546 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/91/7239102.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_7239102
loop_
_publ_author_name
'Duan, Fujun'
'Liu, Miaochang'
'Chen, Jiuxi'
'Ding, Jinchang'
'Hu, Yuefei'
'Wu, Huayue'
_publ_section_title
;
 Copper-catalyzed sequential arylation and intramolecular annulation of
 2-(2-bromophenyl)-2,3-dihydroquinazolin-4(1H)-ones with amidines
;
_journal_issue                   46
_journal_name_full               'RSC Advances'
_journal_page_first              24001
_journal_paper_doi               10.1039/c3ra41969j
_journal_volume                  3
_journal_year                    2013
_chemical_formula_moiety         'C19 H22 N4 O'
_chemical_formula_sum            'C19 H22 N4 O'
_chemical_formula_weight         322.41
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 100.738(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.666(10)
_cell_length_b                   10.849(11)
_cell_length_c                   15.997(16)
_cell_measurement_reflns_used    2358
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.57
_cell_measurement_theta_min      2.21
_cell_volume                     1648(3)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'XP (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Bruker, 2002)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX II area-detector diffractometer'
_diffrn_measurement_method       'φ and ω 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  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0429
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10051
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9876
_exptl_absorpt_correction_T_min  0.9811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3039
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0566
_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)+(0.1208P)²+0.1288P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1773
_refine_ls_wR_factor_ref         0.2063
_reflns_number_gt                2008
_reflns_number_total             3039
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c3ra41969j.txt
_cod_data_source_block           mo_20111101a_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7239102
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
O1 O 0.9337(2) 0.7033(2) 0.14947(13) 0.0807(7) Uani 1 1 d .
N1 N 0.5408(2) 0.7653(2) 0.03592(13) 0.0516(6) Uani 1 1 d .
H1 H 0.4512 0.7593 0.0326 0.062 Uiso 1 1 calc R
N2 N 0.7398(2) 0.8156(2) 0.13321(13) 0.0523(6) Uani 1 1 d .
H2A H 0.7629 0.8451 0.1838 0.063 Uiso 1 1 calc R
N3 N 0.66628(19) 1.11446(19) 0.10606(12) 0.0470(5) Uani 1 1 d .
N4 N 0.8213(2) 1.1003(3) 0.23208(14) 0.0763(8) Uani 1 1 d .
H4A H 0.7432 1.0892 0.2531 0.114 Uiso 1 1 d R
H4B H 0.8723 1.1603 0.2607 0.114 Uiso 1 1 d R
C1 C 0.6134(2) 0.6797(2) 0.00117(15) 0.0456(6) Uani 1 1 d .
C2 C 0.5510(3) 0.6068(3) -0.06532(17) 0.0608(7) Uani 1 1 d .
H2 H 0.4560 0.6170 -0.0883 0.073 Uiso 1 1 calc R
C3 C 0.6260(3) 0.5211(3) -0.0973(2) 0.0694(8) Uani 1 1 d .
H3 H 0.5823 0.4731 -0.1429 0.083 Uiso 1 1 calc R
C4 C 0.7635(3) 0.5029(3) -0.06494(19) 0.0673(8) Uani 1 1 d .
H4 H 0.8152 0.4442 -0.0884 0.081 Uiso 1 1 calc R
C5 C 0.8245(3) 0.5712(3) 0.00210(17) 0.0583(7) Uani 1 1 d .
H5 H 0.9184 0.5570 0.0262 0.070 Uiso 1 1 calc R
C6 C 0.7531(2) 0.6596(2) 0.03509(15) 0.0454(6) Uani 1 1 d .
C7 C 0.8180(2) 0.7273(2) 0.10962(15) 0.0502(6) Uani 1 1 d .
C8 C 0.6170(2) 0.8647(2) 0.07774(16) 0.0488(6) Uani 1 1 d .
H8 H 0.6472 0.9187 0.0354 0.059 Uiso 1 1 calc R
C9 C 0.5323(2) 0.9372(2) 0.12841(14) 0.0453(6) Uani 1 1 d .
C10 C 0.4252(3) 0.8856(3) 0.16083(17) 0.0556(7) Uani 1 1 d .
H10 H 0.4052 0.8023 0.1519 0.067 Uiso 1 1 calc R
C11 C 0.3479(3) 0.9534(3) 0.20567(18) 0.0654(8) Uani 1 1 d .
H11 H 0.2749 0.9169 0.2273 0.079 Uiso 1 1 calc R
C12 C 0.3761(3) 1.0739(3) 0.21921(18) 0.0670(8) Uani 1 1 d .
H12 H 0.3227 1.1207 0.2502 0.080 Uiso 1 1 calc R
C13 C 0.4820(3) 1.1271(3) 0.18782(17) 0.0566(7) Uani 1 1 d .
H13 H 0.5006 1.2105 0.1972 0.068 Uiso 1 1 calc R
C14 C 0.5619(2) 1.0600(2) 0.14257(14) 0.0447(6) Uani 1 1 d .
C15 C 0.7862(3) 1.1329(2) 0.15033(15) 0.0500(6) Uani 1 1 d .
C16 C 0.8985(3) 1.1872(3) 0.11177(17) 0.0607(7) Uani 1 1 d .
C17 C 0.8533(3) 1.1981(4) 0.01713(18) 0.0777(9) Uani 1 1 d .
H17A H 0.8286 1.1182 -0.0067 0.117 Uiso 1 1 calc R
H17B H 0.9292 1.2315 -0.0069 0.117 Uiso 1 1 calc R
H17C H 0.7732 1.2518 0.0044 0.117 Uiso 1 1 calc R
C18 C 0.9328(4) 1.3139(4) 0.1489(2) 0.0913(11) Uani 1 1 d .
H18A H 0.8491 1.3636 0.1395 0.137 Uiso 1 1 calc R
H18B H 1.0028 1.3516 0.1219 0.137 Uiso 1 1 calc R
H18C H 0.9682 1.3069 0.2089 0.137 Uiso 1 1 calc R
C19 C 1.0250(3) 1.1052(4) 0.1299(3) 0.1040(13) Uani 1 1 d .
H19A H 1.0608 1.1038 0.1901 0.156 Uiso 1 1 calc R
H19B H 1.0963 1.1361 0.1009 0.156 Uiso 1 1 calc R
H19C H 0.9992 1.0233 0.1105 0.156 Uiso 1 1 calc R
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'
O O 0.0106 0.0060 '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
C1 N1 C8 117.4(2)
C1 N1 H1 121.3
C8 N1 H1 121.3
C7 N2 C8 122.8(2)
C7 N2 H2A 118.6
C8 N2 H2A 118.6
C15 N3 C14 119.8(2)
C15 N4 H4A 109.1
C15 N4 H4B 108.9
H4A N4 H4B 109.5
N1 C1 C2 122.0(2)
N1 C1 C6 119.7(2)
C2 C1 C6 118.2(2)
C3 C2 C1 120.4(3)
C3 C2 H2 119.8
C1 C2 H2 119.8
C2 C3 C4 121.3(3)
C2 C3 H3 119.3
C4 C3 H3 119.3
C5 C4 C3 118.7(3)
C5 C4 H4 120.7
C3 C4 H4 120.7
C6 C5 C4 121.6(3)
C6 C5 H5 119.2
C4 C5 H5 119.2
C5 C6 C1 119.7(2)
C5 C6 C7 120.8(2)
C1 C6 C7 119.4(2)
O1 C7 N2 122.0(2)
O1 C7 C6 123.0(2)
N2 C7 C6 115.0(2)
N1 C8 N2 107.9(2)
N1 C8 C9 112.0(2)
N2 C8 C9 109.5(2)
N1 C8 H8 109.1
N2 C8 H8 109.1
C9 C8 H8 109.1
C10 C9 C14 119.1(2)
C10 C9 C8 121.8(2)
C14 C9 C8 119.1(2)
C11 C10 C9 121.0(3)
C11 C10 H10 119.5
C9 C10 H10 119.5
C12 C11 C10 120.0(3)
C12 C11 H11 120.0
C10 C11 H11 120.0
C11 C12 C13 120.0(3)
C11 C12 H12 120.0
C13 C12 H12 120.0
C12 C13 C14 120.9(3)
C12 C13 H13 119.6
C14 C13 H13 119.6
C13 C14 C9 119.0(2)
C13 C14 N3 121.7(2)
C9 C14 N3 119.3(2)
N3 C15 N4 123.3(2)
N3 C15 C16 120.3(2)
N4 C15 C16 116.4(2)
C15 C16 C19 108.8(3)
C15 C16 C17 110.9(2)
C19 C16 C17 108.5(3)
C15 C16 C18 109.0(3)
C19 C16 C18 110.7(3)
C17 C16 C18 109.0(3)
C16 C17 H17A 109.5
C16 C17 H17B 109.5
H17A C17 H17B 109.5
C16 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C16 C18 H18A 109.5
C16 C18 H18B 109.5
H18A C18 H18B 109.5
C16 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C16 C19 H19A 109.5
C16 C19 H19B 109.5
H19A C19 H19B 109.5
C16 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.208(3)
N1 C1 1.345(3)
N1 C8 1.404(3)
N1 H1 0.8600
N2 C7 1.317(3)
N2 C8 1.446(3)
N2 H2A 0.8600
N3 C15 1.257(3)
N3 C14 1.388(3)
N4 C15 1.336(3)
N4 H4A 0.8900
N4 H4B 0.8900
C1 C2 1.371(4)
C1 C6 1.375(3)
C2 C3 1.338(4)
C2 H2 0.9300
C3 C4 1.349(4)
C3 H3 0.9300
C4 C5 1.346(4)
C4 H4 0.9300
C5 C6 1.346(4)
C5 H5 0.9300
C6 C7 1.441(4)
C8 C9 1.480(4)
C8 H8 0.9800
C9 C10 1.362(4)
C9 C14 1.373(4)
C10 C11 1.347(4)
C10 H10 0.9300
C11 C12 1.345(5)
C11 H11 0.9300
C12 C13 1.351(4)
C12 H12 0.9300
C13 C14 1.363(4)
C13 H13 0.9300
C15 C16 1.468(4)
C16 C19 1.496(5)
C16 C17 1.500(4)
C16 C18 1.509(5)
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C8 N1 C1 C2 -155.4(3)
C8 N1 C1 C6 27.6(3)
N1 C1 C2 C3 -178.8(3)
C6 C1 C2 C3 -1.8(4)
C1 C2 C3 C4 0.7(5)
C2 C3 C4 C5 1.4(5)
C3 C4 C5 C6 -2.5(5)
C4 C5 C6 C1 1.4(4)
C4 C5 C6 C7 176.7(3)
N1 C1 C6 C5 177.8(2)
C2 C1 C6 C5 0.7(4)
N1 C1 C6 C7 2.5(4)
C2 C1 C6 C7 -174.6(2)
C8 N2 C7 O1 165.6(3)
C8 N2 C7 C6 -16.5(4)
C5 C6 C7 O1 -5.4(4)
C1 C6 C7 O1 169.8(3)
C5 C6 C7 N2 176.7(2)
C1 C6 C7 N2 -8.0(3)
C1 N1 C8 N2 -47.2(3)
C1 N1 C8 C9 -167.8(2)
C7 N2 C8 N1 43.2(3)
C7 N2 C8 C9 165.3(2)
N1 C8 C9 C10 27.2(3)
N2 C8 C9 C10 -92.4(3)
N1 C8 C9 C14 -152.3(2)
N2 C8 C9 C14 88.1(3)
C14 C9 C10 C11 0.5(4)
C8 C9 C10 C11 -178.9(2)
C9 C10 C11 C12 -0.2(4)
C10 C11 C12 C13 0.0(4)
C11 C12 C13 C14 -0.3(4)
C12 C13 C14 C9 0.7(3)
C12 C13 C14 N3 176.6(2)
C10 C9 C14 C13 -0.8(3)
C8 C9 C14 C13 178.7(2)
C10 C9 C14 N3 -176.8(2)
C8 C9 C14 N3 2.7(3)
C15 N3 C14 C13 83.0(3)
C15 N3 C14 C9 -101.2(3)
C14 N3 C15 N4 1.4(4)
C14 N3 C15 C16 178.3(2)
N3 C15 C16 C19 -126.6(3)
N4 C15 C16 C19 50.5(4)
N3 C15 C16 C17 -7.4(4)
N4 C15 C16 C17 169.7(3)
N3 C15 C16 C18 112.7(3)
N4 C15 C16 C18 -70.3(3)
