#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:40:59 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281572 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/90/7159048.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_7159048
loop_
_publ_author_name
'Dutta, Nilakshi'
'Dutta, Bidyutjyoti'
'Dutta, Apurba'
'Sarma, Bipul'
'Sarma, Diganta'
_publ_section_title
;
 Room temperature ligand-free Cu₂O-H₂O₂
 catalyzed tandem oxidative synthesis of quinazoline-4(3H)-one and
 quinazoline derivatives.
;
_journal_issue                   4
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              748
_journal_page_last               753
_journal_paper_doi               10.1039/d2ob02085h
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C15 H12 N2 O'
_chemical_formula_weight         236.27
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-10-17 deposited with the CCDC.	2022-12-22 downloaded from the CCDC.
;
_cell_angle_alpha                94.37(2)
_cell_angle_beta                 93.80(2)
_cell_angle_gamma                97.93(2)
_cell_formula_units_Z            4
_cell_length_a                   4.803(3)
_cell_length_b                   15.071(11)
_cell_length_c                   17.003(12)
_cell_measurement_reflns_used    304
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      12.22
_cell_measurement_theta_min      2.74
_cell_volume                     1211.8(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.4713
_diffrn_reflns_av_unetI/netI     0.3411
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27936
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.410
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.805
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4171
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.805
_refine_ls_R_factor_all          0.3482
_refine_ls_R_factor_gt           0.0635
_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)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.2078
_reflns_Friedel_coverage         0.000
_reflns_number_gt                919
_reflns_number_total             4171
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob02085h2.cif
_cod_data_source_block           BS_NG01
_cod_depositor_comments          'Adding full bibliography for 7159048.cif.'
_cod_original_cell_volume        1211.7(15)
_cod_database_code               7159048
_shelx_shelxl_version_number     2014/7
_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   0.968
_shelx_estimated_absorpt_t_max   0.998
_exptl_absorpt_special_details   SADABS
loop_
_space_group_symop_operation_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_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
O2 O 0.2976(9) -0.0670(3) 0.9297(2) 0.0851(15) Uani 1 1 d . . . . .
O1 O 0.2897(10) 0.4018(3) 0.4801(3) 0.0919(17) Uani 1 1 d . . . . .
N3 N 0.6812(11) 0.0283(4) 0.9018(3) 0.0679(15) Uani 1 1 d . . . . .
H3 H 0.7035 0.0503 0.9503 0.082 Uiso 1 1 calc R U . . .
N1 N 0.6516(11) 0.4217(3) 0.5747(3) 0.0663(15) Uani 1 1 d . . . . .
H1 H 0.6970 0.4758 0.5623 0.080 Uiso 1 1 calc R U . . .
N4 N 0.8506(11) 0.0333(4) 0.7760(3) 0.0664(16) Uani 1 1 d . . . . .
N2 N 0.7631(11) 0.3112(4) 0.6579(3) 0.0718(16) Uani 1 1 d . . . . .
C18 C 0.8681(14) 0.0643(5) 0.8497(4) 0.0621(18) Uani 1 1 d . . . . .
C16 C 0.4535(14) -0.0769(4) 0.8001(4) 0.0617(18) Uani 1 1 d . . . . .
C4 C 0.8129(14) 0.3935(5) 0.6361(4) 0.0635(18) Uani 1 1 d . . . . .
C17 C 0.6417(14) -0.0372(5) 0.7510(4) 0.0592(17) Uani 1 1 d . . . . .
C2 C 0.3770(14) 0.2799(5) 0.5550(4) 0.0622(17) Uani 1 1 d . . . . .
C23 C 1.0889(14) 0.1378(5) 0.8802(4) 0.0690(19) Uani 1 1 d . . . . .
C9 C 1.0436(13) 0.4570(5) 0.6795(4) 0.0617(18) Uani 1 1 d . . . . .
C15 C 0.4628(15) -0.0403(5) 0.8807(4) 0.0629(18) Uani 1 1 d . . . . .
C1 C 0.4289(16) 0.3711(5) 0.5328(5) 0.072(2) Uani 1 1 d . . . . .
C22 C 0.6280(13) -0.0742(5) 0.6713(4) 0.0699(19) Uani 1 1 d . . . . .
H22 H 0.7566 -0.0500 0.6373 0.084 Uiso 1 1 calc R U . . .
C3 C 0.5429(15) 0.2525(5) 0.6169(4) 0.0622(18) Uani 1 1 d . . . . .
C11 C 1.3822(15) 0.5903(4) 0.6910(5) 0.080(2) Uani 1 1 d . . . . .
H11 H 1.4599 0.6421 0.6695 0.096 Uiso 1 1 calc R U . . .
C10 C 1.1618(15) 0.5335(5) 0.6483(4) 0.075(2) Uani 1 1 d . . . . .
H10 H 1.0947 0.5473 0.5988 0.091 Uiso 1 1 calc R U . . .
C19 C 0.2462(13) -0.1484(4) 0.7712(4) 0.0697(19) Uani 1 1 d . . . . .
H19 H 0.1168 -0.1733 0.8046 0.084 Uiso 1 1 calc R U . . .
C12 C 1.4868(15) 0.5724(5) 0.7629(6) 0.079(2) Uani 1 1 d . . . . .
C5 C 0.1550(15) 0.2194(5) 0.5169(4) 0.075(2) Uani 1 1 d . . . . .
H5 H 0.0440 0.2378 0.4760 0.089 Uiso 1 1 calc R U . . .
C25 C 1.4438(15) 0.2585(5) 0.8523(5) 0.084(2) Uani 1 1 d . . . . .
H25 H 1.5344 0.2923 0.8155 0.101 Uiso 1 1 calc R U . . .
C8 C 0.4904(15) 0.1637(5) 0.6366(4) 0.079(2) Uani 1 1 d . . . . .
H8 H 0.6064 0.1443 0.6758 0.094 Uiso 1 1 calc R U . . .
C26 C 1.5287(15) 0.2753(5) 0.9313(5) 0.077(2) Uani 1 1 d . . . . .
C21 C 0.4263(16) -0.1451(5) 0.6441(4) 0.086(2) Uani 1 1 d . . . . .
H21 H 0.4201 -0.1685 0.5917 0.103 Uiso 1 1 calc R U . . .
C27 C 1.3977(15) 0.2250(5) 0.9851(4) 0.081(2) Uani 1 1 d . . . . .
H27 H 1.4553 0.2368 1.0386 0.097 Uiso 1 1 calc R U . . .
C20 C 0.2331(16) -0.1825(5) 0.6925(5) 0.087(2) Uani 1 1 d . . . . .
H20 H 0.0952 -0.2299 0.6730 0.105 Uiso 1 1 calc R U . . .
C28 C 1.1789(14) 0.1564(5) 0.9606(4) 0.075(2) Uani 1 1 d . . . . .
H28 H 1.0912 0.1224 0.9978 0.090 Uiso 1 1 calc R U . . .
C24 C 1.2245(15) 0.1914(5) 0.8278(4) 0.078(2) Uani 1 1 d . . . . .
H24 H 1.1654 0.1818 0.7742 0.094 Uiso 1 1 calc R U . . .
C14 C 1.1493(16) 0.4368(5) 0.7525(5) 0.089(2) Uani 1 1 d . . . . .
H14 H 1.0744 0.3846 0.7741 0.107 Uiso 1 1 calc R U . . .
C7 C 0.2703(16) 0.1047(5) 0.5990(5) 0.083(2) Uani 1 1 d . . . . .
H7 H 0.2360 0.0461 0.6134 0.100 Uiso 1 1 calc R U . . .
C6 C 0.0962(15) 0.1328(5) 0.5385(4) 0.083(2) Uani 1 1 d . . . . .
H6 H -0.0560 0.0936 0.5135 0.099 Uiso 1 1 calc R U . . .
C13 C 1.3713(17) 0.4961(6) 0.7933(4) 0.098(2) Uani 1 1 d . . . . .
H13 H 1.4418 0.4828 0.8427 0.117 Uiso 1 1 calc R U . . .
C29 C 1.7691(13) 0.3515(5) 0.9606(4) 0.100(2) Uani 1 1 d . . . . .
H29A H 1.6942 0.3983 0.9903 0.150 Uiso 1 1 calc R U . . .
H29B H 1.8560 0.3755 0.9160 0.150 Uiso 1 1 calc R U . . .
H29C H 1.9070 0.3284 0.9937 0.150 Uiso 1 1 calc R U . . .
C30 C 1.7262(14) 0.6338(4) 0.8102(4) 0.103(2) Uani 1 1 d . . . . .
H30A H 1.9031 0.6175 0.7955 0.155 Uiso 1 1 calc R U . . .
H30B H 1.7107 0.6279 0.8656 0.155 Uiso 1 1 calc R U . . .
H30C H 1.7163 0.6950 0.7995 0.155 Uiso 1 1 calc R U . . .
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
C15 N3 C18 124.3(6) . . ?
C15 N3 H3 117.9 . . ?
C18 N3 H3 117.9 . . ?
C1 N1 C4 125.2(6) . . ?
C1 N1 H1 117.4 . . ?
C4 N1 H1 117.4 . . ?
C18 N4 C17 117.8(6) . . ?
C4 N2 C3 117.9(6) . . ?
N4 C18 N3 121.2(6) . . ?
N4 C18 C23 120.5(7) . . ?
N3 C18 C23 118.3(7) . . ?
C17 C16 C19 120.9(7) . . ?
C17 C16 C15 118.8(7) . . ?
C19 C16 C15 120.1(7) . . ?
N2 C4 N1 121.5(6) . . ?
N2 C4 C9 118.7(7) . . ?
N1 C4 C9 119.8(7) . . ?
N4 C17 C16 123.6(6) . . ?
N4 C17 C22 118.3(7) . . ?
C16 C17 C22 118.0(7) . . ?
C5 C2 C3 119.3(7) . . ?
C5 C2 C1 120.3(8) . . ?
C3 C2 C1 120.4(7) . . ?
C24 C23 C28 117.1(7) . . ?
C24 C23 C18 119.3(7) . . ?
C28 C23 C18 123.6(7) . . ?
C10 C9 C14 119.3(7) . . ?
C10 C9 C4 122.1(7) . . ?
C14 C9 C4 118.6(7) . . ?
O2 C15 N3 120.9(7) . . ?
O2 C15 C16 125.1(7) . . ?
N3 C15 C16 114.0(7) . . ?
O1 C1 N1 121.5(7) . . ?
O1 C1 C2 125.0(8) . . ?
N1 C1 C2 113.5(7) . . ?
C21 C22 C17 120.3(7) . . ?
C21 C22 H22 119.8 . . ?
C17 C22 H22 119.8 . . ?
N2 C3 C8 119.4(8) . . ?
N2 C3 C2 121.4(7) . . ?
C8 C3 C2 119.2(7) . . ?
C12 C11 C10 121.9(7) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C9 C10 C11 119.8(7) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C20 C19 C16 120.1(6) . . ?
C20 C19 H19 119.9 . . ?
C16 C19 H19 119.9 . . ?
C11 C12 C13 118.2(7) . . ?
C11 C12 C30 122.5(8) . . ?
C13 C12 C30 119.3(9) . . ?
C6 C5 C2 121.4(7) . . ?
C6 C5 H5 119.3 . . ?
C2 C5 H5 119.3 . . ?
C26 C25 C24 119.8(7) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C7 C8 C3 121.0(7) . . ?
C7 C8 H8 119.5 . . ?
C3 C8 H8 119.5 . . ?
C27 C26 C25 120.0(8) . . ?
C27 C26 C29 119.2(7) . . ?
C25 C26 C29 120.8(7) . . ?
C22 C21 C20 121.5(7) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C26 C27 C28 120.5(7) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C21 C20 C19 119.1(7) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C27 C28 C23 120.5(7) . . ?
C27 C28 H28 119.7 . . ?
C23 C28 H28 119.7 . . ?
C25 C24 C23 122.1(7) . . ?
C25 C24 H24 119.0 . . ?
C23 C24 H24 119.0 . . ?
C9 C14 C13 118.8(7) . . ?
C9 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C8 C7 C6 120.0(7) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C5 C6 C7 119.0(7) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C12 C13 C14 121.9(7) . . ?
C12 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C12 C30 H30A 109.5 . . ?
C12 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C12 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
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
O2 C15 1.239(6) . ?
O1 C1 1.239(7) . ?
N3 C15 1.375(7) . ?
N3 C18 1.388(7) . ?
N3 H3 0.8600 . ?
N1 C1 1.351(7) . ?
N1 C4 1.387(7) . ?
N1 H1 0.8600 . ?
N4 C18 1.297(7) . ?
N4 C17 1.377(7) . ?
N2 C4 1.317(7) . ?
N2 C3 1.391(7) . ?
C18 C23 1.461(8) . ?
C16 C17 1.377(7) . ?
C16 C19 1.398(7) . ?
C16 C15 1.434(7) . ?
C4 C9 1.476(8) . ?
C17 C22 1.420(7) . ?
C2 C5 1.392(8) . ?
C2 C3 1.400(7) . ?
C2 C1 1.445(8) . ?
C23 C24 1.384(8) . ?
C23 C28 1.401(7) . ?
C9 C10 1.372(7) . ?
C9 C14 1.381(7) . ?
C22 C21 1.369(8) . ?
C22 H22 0.9300 . ?
C3 C8 1.398(8) . ?
C11 C12 1.351(8) . ?
C11 C10 1.391(8) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
C19 C20 1.390(7) . ?
C19 H19 0.9300 . ?
C12 C13 1.361(9) . ?
C12 C30 1.515(8) . ?
C5 C6 1.379(8) . ?
C5 H5 0.9300 . ?
C25 C26 1.372(8) . ?
C25 C24 1.374(8) . ?
C25 H25 0.9300 . ?
C8 C7 1.372(8) . ?
C8 H8 0.9300 . ?
C26 C27 1.362(8) . ?
C26 C29 1.540(8) . ?
C21 C20 1.372(8) . ?
C21 H21 0.9300 . ?
C27 C28 1.387(8) . ?
C27 H27 0.9300 . ?
C20 H20 0.9300 . ?
C28 H28 0.9300 . ?
C24 H24 0.9300 . ?
C14 C13 1.401(9) . ?
C14 H14 0.9300 . ?
C7 C6 1.410(8) . ?
C7 H7 0.9300 . ?
C6 H6 0.9300 . ?
C13 H13 0.9300 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
