#------------------------------------------------------------------------------
#$Date: 2024-08-05 22:59:05 +0300 (Mon, 05 Aug 2024) $
#$Revision: 293935 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/99/7159991.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_7159991
loop_
_publ_author_name
'Mondal, Shuvam'
'Jana, Ranjan'
_publ_section_title
;
 Green light-mediated dual eosin Y/PdII-catalyzed
 C(sp²)-H arylation of N-H unprotected 2-arylquinazolinones.
;
_journal_issue                   27
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5540
_journal_page_last               5545
_journal_paper_doi               10.1039/d4ob00779d
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C21 H13 N3 O'
_chemical_formula_sum            'C21 H13 N3 O'
_chemical_formula_weight         323.34
_chemical_name_systematic        Quinazolinone
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2024-02-16
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-02-16 deposited with the CCDC.	2024-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.2490(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.7332(2)
_cell_length_b                   20.9652(8)
_cell_length_c                   16.2410(6)
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    122.00
_cell_measurement_theta_max      66.44
_cell_measurement_theta_min      4.22
_cell_volume                     1607.21(11)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      122.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 1K area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22992
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        66.656
_diffrn_reflns_theta_max         66.656
_diffrn_reflns_theta_min         4.217
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_T_max  0.5842
_exptl_absorpt_correction_T_min  0.4070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1283 before and 0.0864 after correction.
The Ratio of minimum to maximum transmission is 0.6967.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             672
_exptl_crystal_preparation       'slow evaporation'
_exptl_crystal_recrystallization_method 'DCM and Hexane'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2803
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0451
_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)+(0.0690P)²+0.4505P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1214
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2660
_reflns_number_total             2803
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00779d2.cif
_cod_data_source_block           shm_305_0m_a
_cod_depositor_comments
'Adding full bibliography for 7159991--7159992.cif.'
_cod_original_cell_volume        1607.20(11)
_cod_database_code               7159991
_shelx_shelxl_version_number     2018/3
_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_max   0.935
_shelx_estimated_absorpt_t_min   0.813
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00L(H00L), C00M(H00M), C00O(H00O), C00P(H00P)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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
O001 O 0.9231(2) 0.49886(5) 0.39899(6) 0.0369(3) Uani 1 1 d . . . . .
N002 N 0.4508(2) 0.34207(5) 0.44814(7) 0.0260(3) Uani 1 1 d . . . . .
N003 N 0.7814(2) 0.42259(5) 0.48676(7) 0.0274(3) Uani 1 1 d . . . . .
N004 N 1.1815(3) 0.03644(7) 0.38771(9) 0.0477(4) Uani 1 1 d . . . . .
C005 C 0.6223(3) 0.36966(6) 0.50295(8) 0.0248(3) Uani 1 1 d . . . . .
C006 C 0.7539(3) 0.23150(6) 0.55443(8) 0.0245(3) Uani 1 1 d . . . . .
C007 C 0.5405(3) 0.45004(6) 0.26934(8) 0.0284(3) Uani 1 1 d . . . . .
H007 H 0.652532 0.485337 0.254883 0.034 Uiso 1 1 calc R U . . .
C008 C 0.6734(3) 0.28224(6) 0.61210(8) 0.0254(3) Uani 1 1 d . . . . .
C009 C 0.6409(3) 0.34716(6) 0.59014(8) 0.0264(3) Uani 1 1 d . . . . .
C00A C 0.4228(3) 0.36958(6) 0.36990(8) 0.0250(3) Uani 1 1 d . . . . .
C00B C 0.5792(3) 0.42309(6) 0.34828(8) 0.0253(3) Uani 1 1 d . . . . .
C00C C 0.9601(3) 0.24225(6) 0.49878(8) 0.0266(3) Uani 1 1 d . . . . .
H00C H 1.033129 0.284049 0.492611 0.032 Uiso 1 1 calc R U . . .
C00D C 0.6467(3) 0.16963(6) 0.56107(8) 0.0284(3) Uani 1 1 d . . . . .
H00D H 0.501742 0.161873 0.597266 0.034 Uiso 1 1 calc R U . . .
C00E C 0.3395(3) 0.42515(6) 0.21293(9) 0.0303(3) Uani 1 1 d . . . . .
H00E H 0.308011 0.443980 0.159844 0.036 Uiso 1 1 calc R U . . .
C00F C 0.7470(3) 0.11963(6) 0.51618(9) 0.0303(3) Uani 1 1 d . . . . .
H00F H 0.674113 0.077813 0.522299 0.036 Uiso 1 1 calc R U . . .
C00G C 0.2234(3) 0.34382(7) 0.31057(9) 0.0291(3) Uani 1 1 d . . . . .
H00G H 0.117610 0.307056 0.323267 0.035 Uiso 1 1 calc R U . . .
C00H C 1.0590(3) 0.19278(6) 0.45259(8) 0.0297(3) Uani 1 1 d . . . . .
H00H H 1.197599 0.200826 0.414453 0.036 Uiso 1 1 calc R U . . .
C00I C 0.1815(3) 0.37197(7) 0.23394(9) 0.0319(3) Uani 1 1 d . . . . .
H00I H 0.042773 0.354956 0.194698 0.038 Uiso 1 1 calc R U . . .
C00J C 0.7755(3) 0.45167(6) 0.41069(9) 0.0279(3) Uani 1 1 d . . . . .
C00K C 0.9557(3) 0.13093(6) 0.46187(8) 0.0297(3) Uani 1 1 d . . . . .
C00L C 0.6516(3) 0.26570(7) 0.69470(9) 0.0305(3) Uani 1 1 d . . . . .
H00L H 0.667909 0.222112 0.710322 0.037 Uiso 1 1 calc R U . . .
C00M C 0.6019(3) 0.39236(7) 0.65142(9) 0.0339(3) Uani 1 1 d . . . . .
H00M H 0.586509 0.436157 0.636765 0.041 Uiso 1 1 calc R U . . .
C00N C 1.0768(3) 0.07843(7) 0.41924(9) 0.0357(4) Uani 1 1 d . . . . .
C00O C 0.6068(3) 0.31099(7) 0.75458(9) 0.0365(4) Uani 1 1 d . . . . .
H00O H 0.591010 0.298255 0.810192 0.044 Uiso 1 1 calc R U . . .
C00P C 0.5853(4) 0.37474(7) 0.73314(10) 0.0392(4) Uani 1 1 d . . . . .
H00P H 0.559396 0.406146 0.774065 0.047 Uiso 1 1 calc R U . . .
H003 H 0.897(4) 0.4447(10) 0.5288(13) 0.057(5) Uiso 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C005 N002 C00A 117.03(11) . . ?
C005 N003 H003 122.9(12) . . ?
C00J N003 C005 123.59(12) . . ?
C00J N003 H003 113.3(12) . . ?
N002 C005 N003 123.51(12) . . ?
N002 C005 C009 120.12(11) . . ?
N003 C005 C009 116.24(11) . . ?
C00C C006 C008 121.11(11) . . ?
C00C C006 C00D 118.30(12) . . ?
C00D C006 C008 120.23(12) . . ?
C00B C007 H007 120.2 . . ?
C00E C007 H007 120.2 . . ?
C00E C007 C00B 119.63(13) . . ?
C009 C008 C006 123.99(12) . . ?
C00L C008 C006 117.93(11) . . ?
C00L C008 C009 117.86(12) . . ?
C008 C009 C005 122.90(12) . . ?
C00M C009 C005 117.46(12) . . ?
C00M C009 C008 119.45(13) . . ?
N002 C00A C00B 122.88(12) . . ?
N002 C00A C00G 118.69(12) . . ?
C00B C00A C00G 118.40(12) . . ?
C007 C00B C00A 121.05(12) . . ?
C007 C00B C00J 120.39(12) . . ?
C00A C00B C00J 118.51(12) . . ?
C006 C00C H00C 119.6 . . ?
C00H C00C C006 120.75(12) . . ?
C00H C00C H00C 119.6 . . ?
C006 C00D H00D 119.3 . . ?
C00F C00D C006 121.46(13) . . ?
C00F C00D H00D 119.3 . . ?
C007 C00E H00E 120.1 . . ?
C007 C00E C00I 119.77(13) . . ?
C00I C00E H00E 120.1 . . ?
C00D C00F H00F 120.2 . . ?
C00D C00F C00K 119.54(12) . . ?
C00K C00F H00F 120.2 . . ?
C00A C00G H00G 120.0 . . ?
C00I C00G C00A 119.92(13) . . ?
C00I C00G H00G 120.0 . . ?
C00C C00H H00H 119.9 . . ?
C00C C00H C00K 120.16(13) . . ?
C00K C00H H00H 119.9 . . ?
C00E C00I H00I 119.4 . . ?
C00G C00I C00E 121.18(13) . . ?
C00G C00I H00I 119.4 . . ?
O001 C00J N003 121.28(12) . . ?
O001 C00J C00B 124.30(12) . . ?
N003 C00J C00B 114.41(11) . . ?
C00F C00K C00H 119.76(13) . . ?
C00F C00K C00N 120.02(13) . . ?
C00H C00K C00N 120.11(13) . . ?
C008 C00L H00L 119.0 . . ?
C00O C00L C008 121.98(13) . . ?
C00O C00L H00L 119.0 . . ?
C009 C00M H00M 119.3 . . ?
C00P C00M C009 121.44(13) . . ?
C00P C00M H00M 119.3 . . ?
N004 C00N C00K 177.35(17) . . ?
C00L C00O H00O 120.1 . . ?
C00P C00O C00L 119.82(14) . . ?
C00P C00O H00O 120.1 . . ?
C00M C00P H00P 120.3 . . ?
C00O C00P C00M 119.38(14) . . ?
C00O C00P H00P 120.3 . . ?
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
O001 C00J 1.2340(16) . ?
N002 C005 1.2956(17) . ?
N002 C00A 1.3928(17) . ?
N003 C005 1.3773(17) . ?
N003 C00J 1.3762(18) . ?
N003 H003 0.96(2) . ?
N004 C00N 1.149(2) . ?
C005 C009 1.4889(18) . ?
C006 C008 1.4855(19) . ?
C006 C00C 1.3966(19) . ?
C006 C00D 1.4000(18) . ?
C007 H007 0.9500 . ?
C007 C00B 1.4006(19) . ?
C007 C00E 1.374(2) . ?
C008 C009 1.4125(18) . ?
C008 C00L 1.3969(19) . ?
C009 C00M 1.396(2) . ?
C00A C00B 1.4032(18) . ?
C00A C00G 1.4058(19) . ?
C00B C00J 1.4524(19) . ?
C00C H00C 0.9500 . ?
C00C C00H 1.3820(19) . ?
C00D H00D 0.9500 . ?
C00D C00F 1.381(2) . ?
C00E H00E 0.9500 . ?
C00E C00I 1.399(2) . ?
C00F H00F 0.9500 . ?
C00F C00K 1.393(2) . ?
C00G H00G 0.9500 . ?
C00G C00I 1.378(2) . ?
C00H H00H 0.9500 . ?
C00H C00K 1.3980(19) . ?
C00I H00I 0.9500 . ?
C00K C00N 1.442(2) . ?
C00L H00L 0.9500 . ?
C00L C00O 1.387(2) . ?
C00M H00M 0.9500 . ?
C00M C00P 1.386(2) . ?
C00O H00O 0.9500 . ?
C00O C00P 1.383(2) . ?
C00P H00P 0.9500 . ?
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
N002 C005 C009 C008 48.82(18) . . . . ?
N002 C005 C009 C00M -126.11(14) . . . . ?
N002 C00A C00B C007 -178.72(12) . . . . ?
N002 C00A C00B C00J -1.07(19) . . . . ?
N002 C00A C00G C00I 176.87(12) . . . . ?
N003 C005 C009 C008 -135.09(13) . . . . ?
N003 C005 C009 C00M 49.98(17) . . . . ?
C005 N002 C00A C00B 2.75(19) . . . . ?
C005 N002 C00A C00G -175.38(12) . . . . ?
C005 N003 C00J O001 -179.61(12) . . . . ?
C005 N003 C00J C00B 1.80(19) . . . . ?
C005 C009 C00M C00P 173.00(14) . . . . ?
C006 C008 C009 C005 13.7(2) . . . . ?
C006 C008 C009 C00M -171.49(12) . . . . ?
C006 C008 C00L C00O 173.15(13) . . . . ?
C006 C00C C00H C00K -0.8(2) . . . . ?
C006 C00D C00F C00K -1.2(2) . . . . ?
C007 C00B C00J O001 -2.0(2) . . . . ?
C007 C00B C00J N003 176.52(11) . . . . ?
C007 C00E C00I C00G 0.0(2) . . . . ?
C008 C006 C00C C00H 171.94(12) . . . . ?
C008 C006 C00D C00F -171.00(12) . . . . ?
C008 C009 C00M C00P -2.1(2) . . . . ?
C008 C00L C00O C00P -0.6(2) . . . . ?
C009 C008 C00L C00O -1.6(2) . . . . ?
C009 C00M C00P C00O -0.2(2) . . . . ?
C00A N002 C005 N003 -2.17(19) . . . . ?
C00A N002 C005 C009 173.62(11) . . . . ?
C00A C00B C00J O001 -179.69(13) . . . . ?
C00A C00B C00J N003 -1.15(18) . . . . ?
C00A C00G C00I C00E 1.7(2) . . . . ?
C00B C007 C00E C00I -1.9(2) . . . . ?
C00B C00A C00G C00I -1.3(2) . . . . ?
C00C C006 C008 C009 40.55(19) . . . . ?
C00C C006 C008 C00L -133.90(13) . . . . ?
C00C C006 C00D C00F 2.14(19) . . . . ?
C00C C00H C00K C00F 1.8(2) . . . . ?
C00C C00H C00K C00N -174.45(13) . . . . ?
C00D C006 C008 C009 -146.50(13) . . . . ?
C00D C006 C008 C00L 39.05(18) . . . . ?
C00D C006 C00C C00H -1.14(19) . . . . ?
C00D C00F C00K C00H -0.8(2) . . . . ?
C00D C00F C00K C00N 175.44(13) . . . . ?
C00E C007 C00B C00A 2.2(2) . . . . ?
C00E C007 C00B C00J -175.37(12) . . . . ?
C00G C00A C00B C007 -0.59(19) . . . . ?
C00G C00A C00B C00J 177.06(12) . . . . ?
C00J N003 C005 N002 -0.1(2) . . . . ?
C00J N003 C005 C009 -176.06(12) . . . . ?
C00L C008 C009 C005 -171.86(12) . . . . ?
C00L C008 C009 C00M 2.97(19) . . . . ?
C00L C00O C00P C00M 1.6(2) . . . . ?
