#------------------------------------------------------------------------------
#$Date: 2020-10-06 12:14:50 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257582 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240446.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_7240446
loop_
_publ_author_name
'Hadian, Mojgan'
'Shaabani, Shabnam'
'Patil, Pravin'
'Shishkina, Svitlana V.'
'Böltz, Harry'
'Dömling, Alexander'
_publ_section_title
;
 Sustainability by design: automated nanoscale 2,3,4-trisubstituted
 quinazoline diversity
;
_journal_issue                   8
_journal_name_full               'Green Chemistry'
_journal_page_first              2459
_journal_page_last               2467
_journal_paper_doi               10.1039/D0GC00363H
_journal_volume                  22
_journal_year                    2020
_chemical_formula_sum            'C11 H9 N O4'
_chemical_formula_weight         219.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2019-11-29 deposited with the CCDC.	2020-02-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.39(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.522(5)
_cell_length_b                   3.8101(12)
_cell_length_c                   26.193(8)
_cell_measurement_reflns_used    465
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.807
_cell_measurement_theta_min      4.009
_cell_volume                     2000.4(10)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1005
_diffrn_reflns_av_unetI/netI     0.1078
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            9140
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_min         3.391
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.03238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_description       stick
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.858
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2930
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.858
_refine_ls_R_factor_all          0.2002
_refine_ls_R_factor_gt           0.0758
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0940P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1904
_refine_ls_wR_factor_ref         0.2470
_reflns_Friedel_coverage         0.000
_reflns_number_gt                933
_reflns_number_total             2930
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0gc00363h2.cif
_cod_data_source_block           ad26
_cod_depositor_comments
'Adding full bibliography for 7240443--7240446.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7240446
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.967
_shelx_estimated_absorpt_t_max   0.994
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.56941(13) -0.0067(8) 0.53876(10) 0.0992(9) Uani 1 1 d . . . . .
O2 O 0.43111(10) 0.4394(6) 0.65667(8) 0.0822(7) Uani 1 1 d . . . . .
O3 O 0.24094(12) 0.8567(7) 0.57243(10) 0.0979(9) Uani 1 1 d . . . . .
O4 O 0.31629(12) 0.7102(8) 0.64143(9) 0.0936(8) Uani 1 1 d . . . . .
H4O H 0.352542 0.610548 0.648262 0.140 Uiso 1 1 calc R U . . .
N1 N 0.50112(11) 0.2236(6) 0.60863(9) 0.0653(7) Uani 1 1 d . . . . .
H1N H 0.504932 0.189628 0.576947 0.078 Uiso 1 1 calc R U . . .
C1 C 0.55599(14) 0.1103(8) 0.64757(12) 0.0624(8) Uani 1 1 d . . . . .
C2 C 0.55756(17) 0.1457(9) 0.69998(13) 0.0755(9) Uani 1 1 d . . . . .
H2 H 0.521610 0.245063 0.711116 0.091 Uiso 1 1 calc R U . . .
C3 C 0.61377(17) 0.0310(9) 0.73659(14) 0.0813(10) Uani 1 1 d . . . . .
H3 H 0.614872 0.055022 0.772096 0.098 Uiso 1 1 calc R U . . .
C4 C 0.66673(17) -0.1150(9) 0.72087(15) 0.0795(10) Uani 1 1 d . . . . .
H4 H 0.703832 -0.188423 0.745560 0.095 Uiso 1 1 calc R U . . .
C5 C 0.66533(16) -0.1537(8) 0.66858(15) 0.0765(9) Uani 1 1 d . . . . .
H5 H 0.701560 -0.254180 0.657982 0.092 Uiso 1 1 calc R U . . .
C6 C 0.61014(14) -0.0441(8) 0.63121(12) 0.0633(8) Uani 1 1 d . . . . .
C7 C 0.61205(17) -0.0918(9) 0.57696(15) 0.0801(10) Uani 1 1 d . . . . .
H7 H 0.650011 -0.199456 0.570241 0.096 Uiso 1 1 calc R U . . .
C8 C 0.44366(15) 0.3773(8) 0.61392(12) 0.0634(8) Uani 1 1 d . . . . .
C9 C 0.39790(15) 0.4602(8) 0.56370(11) 0.0706(9) Uani 1 1 d . . . . .
H9 H 0.413796 0.406243 0.533950 0.085 Uiso 1 1 calc R U . . .
C10 C 0.33694(16) 0.6015(9) 0.55493(13) 0.0768(10) Uani 1 1 d . . . . .
H10 H 0.317079 0.625475 0.519697 0.092 Uiso 1 1 calc R U . . .
C11 C 0.29504(17) 0.7271(9) 0.59061(14) 0.0759(9) Uani 1 1 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O4 H4O 109.5 . . ?
C8 N1 C1 129.5(3) . . ?
C8 N1 H1N 115.3 . . ?
C1 N1 H1N 115.3 . . ?
C2 C1 C6 119.8(3) . . ?
C2 C1 N1 122.3(3) . . ?
C6 C1 N1 117.9(3) . . ?
C1 C2 C3 119.5(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.9(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 119.3(3) . . ?
C5 C6 C7 117.7(3) . . ?
C1 C6 C7 123.0(3) . . ?
O1 C7 C6 127.4(3) . . ?
O1 C7 H7 116.3 . . ?
C6 C7 H7 116.3 . . ?
O2 C8 N1 122.5(3) . . ?
O2 C8 C9 123.7(3) . . ?
N1 C8 C9 113.8(3) . . ?
C10 C9 C8 129.2(3) . . ?
C10 C9 H9 115.4 . . ?
C8 C9 H9 115.4 . . ?
C9 C10 C11 132.2(3) . . ?
C9 C10 H10 113.9 . . ?
C11 C10 H10 113.9 . . ?
O3 C11 O4 119.7(3) . . ?
O3 C11 C10 119.4(3) . . ?
O4 C11 C10 120.9(3) . . ?
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
O1 C7 1.223(4) . ?
O2 C8 1.224(3) . ?
O3 C11 1.215(4) . ?
O4 C11 1.310(4) . ?
O4 H4O 0.8200 . ?
N1 C8 1.350(4) . ?
N1 C1 1.415(4) . ?
N1 H1N 0.8600 . ?
C1 C2 1.373(4) . ?
C1 C6 1.403(4) . ?
C2 C3 1.402(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.361(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.441(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.477(4) . ?
C9 C10 1.336(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.479(4) . ?
C10 H10 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.86 1.97 2.680(3) 139.2 .
O4 H4O O2 0.82 1.71 2.524(3) 172.4 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 0.1(5) . . . . ?
C8 N1 C1 C6 179.9(3) . . . . ?
C6 C1 C2 C3 0.8(5) . . . . ?
N1 C1 C2 C3 -179.4(3) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
C4 C5 C6 C1 0.6(5) . . . . ?
C4 C5 C6 C7 179.8(3) . . . . ?
C2 C1 C6 C5 -1.1(5) . . . . ?
N1 C1 C6 C5 179.1(3) . . . . ?
C2 C1 C6 C7 179.7(3) . . . . ?
N1 C1 C6 C7 -0.1(4) . . . . ?
C5 C6 C7 O1 -178.4(3) . . . . ?
C1 C6 C7 O1 0.8(6) . . . . ?
C1 N1 C8 O2 -0.6(5) . . . . ?
C1 N1 C8 C9 179.7(3) . . . . ?
O2 C8 C9 C10 -1.8(6) . . . . ?
N1 C8 C9 C10 177.9(3) . . . . ?
C8 C9 C10 C11 1.1(7) . . . . ?
C9 C10 C11 O3 177.9(4) . . . . ?
C9 C10 C11 O4 0.0(6) . . . . ?
