#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/37/7233765.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_7233765
loop_
_publ_author_name
'Aziz, Marian N.'
'Panda, Siva S.'
'Shalaby, ElSayed M.'
'Fawzy, Nehmedo G.'
'Girgis, Adel S.'
_publ_section_title
;
 Facile synthetic approach towards vasorelaxant active
 4-hydroxyquinazoline-4-carboxamides
;
_journal_issue                   49
_journal_name_full               'RSC Advances'
_journal_page_first              28534
_journal_paper_doi               10.1039/C9RA04321G
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C11 H10 N2 O3'
_chemical_formula_sum            'C11 H10 N2 O3'
_chemical_formula_weight         218.21
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_update_record
;
2019-04-30 deposited with the CCDC.    2019-09-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.02(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.926(2)
_cell_length_b                   21.310(4)
_cell_length_c                   8.9155(18)
_cell_measurement_reflns_used    1863
_cell_measurement_temperature    293
_cell_measurement_theta_max      30
_cell_measurement_theta_min      2
_cell_volume                     2070.7(7)
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_data_reduction        'USER DEFINED DATA REDUCTION'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       Serial
_diffrn_measurement_device_type  Unknown
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.70000
_diffrn_reflns_av_R_equivalents  0.024
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            26527
_diffrn_reflns_theta_full        28.495
_diffrn_reflns_theta_max         30.973
_diffrn_reflns_theta_min         1.882
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.32
_refine_ls_extinction_coef       6900(400)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.1993
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         3317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0664
_refine_ls_shift/su_max          0.0003406
_refine_ls_shift/su_mean         0.0000396
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 73.2 117. 59.0 15.4 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1848
_refine_ls_wR_factor_gt          0.1847
_refine_ls_wR_factor_ref         0.1847
_reflns_limit_h_max              15
_reflns_limit_h_min              -16
_reflns_limit_k_max              31
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                3317
_reflns_number_total             3404
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   3.21
_oxford_diffrn_Wilson_scale      2.21
_oxford_refine_ls_r_factor_ref   0.0664
_oxford_refine_ls_scale          0.881(8)
_oxford_reflns_number_all        3397
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_publcif_datablock.id            {a7f422b1-ccc4-4c07-82d6-764c239e43a8}
_cod_data_source_file            c9ra04321g2.cif
_cod_data_source_block           5PK
_cod_original_cell_volume        2070.7(4)
_cod_original_sg_symbol_H-M      'C 2/c '
_cod_database_code               7233765
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
x,-y,z+1/2
-x,y,-z+1/2
x+1/2,-y+1/2,z+1/2
-x+1/2,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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
O1 O 0.20375(9) 0.35437(5) 0.23820(10) 0.0590 1.0000 Uani .
C2 C 0.14991(8) 0.38338(5) 0.33084(10) 0.0434 1.0000 Uani D
N3 N 0.07450(7) 0.35055(4) 0.43001(9) 0.0403 1.0000 Uani .
C4 C 0.06452(8) 0.28351(4) 0.43740(9) 0.0383 1.0000 Uani .
C5 C 0.13475(9) 0.23823(5) 0.37105(12) 0.0464 1.0000 Uani .
C6 C 0.10768(13) 0.17585(5) 0.40066(15) 0.0570 1.0000 Uani .
C7 C 0.01447(15) 0.15841(6) 0.49025(17) 0.0633 1.0000 Uani .
C8 C -0.05567(11) 0.20383(6) 0.55700(13) 0.0559 1.0000 Uani .
C9 C -0.02872(9) 0.26652(4) 0.52987(11) 0.0436 1.0000 Uani .
C10 C -0.08007(10) 0.32336(5) 0.58918(12) 0.0461 1.0000 Uani .
C11 C -0.00927(9) 0.37783(5) 0.52080(11) 0.0437 1.0000 Uani .
O12 O -0.02547(10) 0.43315(4) 0.54362(11) 0.0601 1.0000 Uani .
O13 O -0.15738(10) 0.33184(5) 0.67834(12) 0.0678 1.0000 Uani .
N14 N 0.15157(11) 0.44586(5) 0.34773(13) 0.0583 1.0000 Uani D
C15 C 0.21865(15) 0.48651(7) 0.25064(16) 0.0651 1.0000 Uani D
C16 C 0.3376(2) 0.50572(15) 0.3192(4) 0.1298 1.0000 Uani .
H51 H 0.1980 0.2494 0.3083 0.0389 1.0000 Uiso R
H61 H 0.1550 0.1439 0.3579 0.0504 1.0000 Uiso R
H71 H -0.0010 0.1152 0.5069 0.0553 1.0000 Uiso R
H81 H -0.1203 0.1926 0.6178 0.0501 1.0000 Uiso R
H151 H 0.1697 0.5224 0.2255 0.0626 1.0000 Uiso R
H152 H 0.2317 0.4635 0.1619 0.0626 1.0000 Uiso R
H161 H 0.3783 0.5315 0.2514 0.1477 1.0000 Uiso R
H162 H 0.3246 0.5288 0.4079 0.1477 1.0000 Uiso R
H163 H 0.3866 0.4699 0.3443 0.1477 1.0000 Uiso R
H141 H 0.1035(15) 0.4641(7) 0.4158(17) 0.0672 1.0000 Uiso D
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508
'International Tables Vol C 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_publ_flag
O1 C2 N3 119.83(10) yes
O1 C2 N14 125.33(10) yes
N3 C2 N14 114.82(8) yes
C2 N3 C4 124.30(8) yes
C2 N3 C11 125.84(9) yes
C4 N3 C11 109.53(7) yes
N3 C4 C5 128.72(9) yes
N3 C4 C9 110.16(8) yes
C5 C4 C9 121.09(10) yes
C4 C5 C6 116.82(11) yes
C4 C5 H51 121.5 no
C6 C5 H51 121.7 no
C5 C6 C7 122.64(11) yes
C5 C6 H61 118.6 no
C7 C6 H61 118.7 no
C6 C7 C8 120.48(11) yes
C6 C7 H71 119.7 no
C8 C7 H71 119.9 no
C7 C8 C9 117.57(11) yes
C7 C8 H81 121.5 no
C9 C8 H81 121.0 no
C4 C9 C8 121.38(10) yes
C4 C9 C10 108.33(8) yes
C8 C9 C10 130.23(10) yes
C9 C10 C11 105.46(8) yes
C9 C10 O13 131.93(10) yes
C11 C10 O13 122.53(10) yes
C10 C11 N3 106.49(8) yes
C10 C11 O12 125.61(9) yes
N3 C11 O12 127.90(9) yes
C2 N14 C15 121.81(10) yes
C2 N14 H141 119.5(9) no
C15 N14 H141 118.4(9) no
N14 C15 C16 112.90(15) yes
N14 C15 H151 108.7 no
C16 C15 H151 110.1 no
N14 C15 H152 107.4 no
C16 C15 H152 108.2 no
H151 C15 H152 109.5 no
C15 C16 H161 109.9 no
C15 C16 H162 108.3 no
H161 C16 H162 109.5 no
C15 C16 H163 110.2 no
H161 C16 H163 109.5 no
H162 C16 H163 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 1.2160(12) yes
C2 N3 1.4325(11) yes
C2 N14 1.3398(15) yes
N3 C4 1.4347(12) yes
N3 C11 1.3910(11) yes
C4 C5 1.3904(13) yes
C4 C9 1.4023(13) yes
C5 C6 1.3911(17) yes
C5 H51 0.950 no
C6 C7 1.388(2) yes
C6 H61 0.950 no
C7 C8 1.394(2) yes
C7 H71 0.950 no
C8 C9 1.3929(14) yes
C8 H81 0.950 no
C9 C10 1.4501(15) yes
C10 C11 1.5439(14) yes
C10 O13 1.2134(12) yes
C11 O12 1.2114(12) yes
N14 C15 1.4582(14) yes
N14 H141 0.917(14) no
C15 C16 1.455(3) yes
C15 H151 0.950 no
C15 H152 0.950 no
C16 H161 0.950 no
C16 H162 0.950 no
C16 H163 0.950 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 15750109
