#------------------------------------------------------------------------------
#$Date: 2025-04-03 08:32:21 +0300 (Thu, 03 Apr 2025) $
#$Revision: 298703 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/99/7159992.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_7159992
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 H15 F N2 O2'
_chemical_formula_sum            'C21 H15 F N2 O2'
_chemical_formula_weight         446.35
_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             2024-05-06
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-05-06 deposited with the CCDC.	2024-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.812(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4997(6)
_cell_length_b                   13.6212(11)
_cell_length_c                   16.1797(12)
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      67.00
_cell_measurement_theta_min      4.25
_cell_volume                     1649.2(2)
_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      100.00
_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 0.978
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 1K area detector'
_diffrn_measurement_method       '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  0.0776
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24330
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.661
_diffrn_reflns_theta_min         4.247
_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    0.812
_exptl_absorpt_correction_T_max  0.5842
_exptl_absorpt_correction_T_min  0.3909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1442 before and 0.1001 after correction.
The Ratio of minimum to maximum transmission is 0.6691.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             720
_exptl_crystal_preparation       'chloroform and hexane'
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0080(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         2914
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0682
_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)+(0.0331P)²+3.3167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1471
_refine_ls_wR_factor_ref         0.1533
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2766
_reflns_number_total             2914
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob00779d2.cif
_cod_data_source_block           shm_420_0m_a
_cod_depositor_comments
;
Adding full bibliography for 7159991--7159992.cif.

2025-04-01
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C84 H60 F4 N8 O8'
_cod_original_formula_weight         1385.40
_cod_original_formula_moiety         '4(C21 H15 F N2 O2)'
_cod_original_formula_units_Z            1
_cod_database_code               7159992
_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   0.930
_shelx_estimated_absorpt_t_min   0.854
_olex2_refinement_description
;
1.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00F(H00F), C00G(H00G), C00H(H00H), C00J(H00J),
 C00K(H00K), C00M(H00M), C00N(H00N), C00O(H00O), C00Q(H00Q)
1.b Idealised Me refined as rotating group:
 C00P(H00A,H00B,H00C)
;
_olex2_submission_original_sample_id SHM-420
_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
F001 F -0.0144(2) 0.18844(13) 0.60481(10) 0.0361(5) Uani 1 1 d . . . . .
O002 O 0.3163(3) 0.57133(16) 0.48013(12) 0.0340(5) Uani 1 1 d . . . . .
O003 O 0.1285(3) 0.09201(16) 0.48543(12) 0.0341(5) Uani 1 1 d . . . . .
N004 N 0.3934(3) 0.49620(19) 0.60310(15) 0.0293(6) Uani 1 1 d . . . . .
N005 N 0.2222(3) 0.50691(18) 0.72045(14) 0.0292(6) Uani 1 1 d . . . . .
C006 C 0.2786(4) 0.5499(2) 0.55094(17) 0.0286(7) Uani 1 1 d . . . . .
C007 C 0.3627(4) 0.4767(2) 0.68456(17) 0.0281(6) Uani 1 1 d . . . . .
C008 C -0.0667(4) 0.5838(2) 0.70545(18) 0.0310(7) Uani 1 1 d . . . . .
H008 H -0.081746 0.571666 0.762378 0.037 Uiso 1 1 calc R U . . .
C009 C 0.2594(4) 0.2579(2) 0.65341(18) 0.0298(7) Uani 1 1 d . . . . .
H009 H 0.200544 0.292533 0.694656 0.036 Uiso 1 1 calc R U . . .
C00A C 0.1651(3) 0.1983(2) 0.59878(18) 0.0291(7) Uani 1 1 d . . . . .
C00B C 0.4456(4) 0.2674(2) 0.64803(18) 0.0291(7) Uani 1 1 d . . . . .
C00C C 0.5039(4) 0.4209(2) 0.73362(17) 0.0282(7) Uani 1 1 d . . . . .
C00D C 0.1130(4) 0.5785(2) 0.58688(18) 0.0280(6) Uani 1 1 d . . . . .
C00E C 0.2418(4) 0.1466(2) 0.53575(17) 0.0287(6) Uani 1 1 d . . . . .
C00F C 0.5893(4) 0.4663(2) 0.80251(18) 0.0306(7) Uani 1 1 d . . . . .
H00F H 0.553895 0.530403 0.817803 0.037 Uiso 1 1 calc R U . . .
C00G C 0.4251(4) 0.1565(2) 0.52977(18) 0.0308(7) Uani 1 1 d . . . . .
H00G H 0.482211 0.122895 0.487399 0.037 Uiso 1 1 calc R U . . .
C00H C 0.7256(4) 0.4190(2) 0.84904(19) 0.0334(7) Uani 1 1 d . . . . .
H00H H 0.781651 0.449687 0.896673 0.040 Uiso 1 1 calc R U . . .
C00I C 0.0927(4) 0.5557(2) 0.67055(18) 0.0285(7) Uani 1 1 d . . . . .
C00J C -0.2005(4) 0.6289(2) 0.65717(19) 0.0333(7) Uani 1 1 d . . . . .
H00J H -0.308050 0.646807 0.681109 0.040 Uiso 1 1 calc R U . . .
C00K C -0.0238(4) 0.6249(2) 0.53903(18) 0.0305(7) Uani 1 1 d . . . . .
H00K H -0.008668 0.640032 0.482617 0.037 Uiso 1 1 calc R U . . .
C00L C 0.5515(4) 0.3251(2) 0.71169(18) 0.0297(7) Uani 1 1 d . . . . .
C00M C 0.5253(4) 0.2157(2) 0.58585(18) 0.0297(7) Uani 1 1 d . . . . .
H00M H 0.650704 0.220947 0.581572 0.036 Uiso 1 1 calc R U . . .
C00N C -0.1812(4) 0.6486(2) 0.57380(19) 0.0329(7) Uani 1 1 d . . . . .
H00N H -0.276081 0.678396 0.540986 0.040 Uiso 1 1 calc R U . . .
C00O C 0.6920(4) 0.2796(2) 0.75794(19) 0.0349(7) Uani 1 1 d . . . . .
H00O H 0.728427 0.215604 0.743035 0.042 Uiso 1 1 calc R U . . .
C00P C 0.2021(4) 0.0485(3) 0.4149(2) 0.0395(8) Uani 1 1 d . . . . .
H00A H 0.252718 0.099855 0.381084 0.059 Uiso 1 1 calc R U . . .
H00B H 0.107786 0.013681 0.381808 0.059 Uiso 1 1 calc R U . . .
H00C H 0.296261 0.001986 0.433308 0.059 Uiso 1 1 calc R U . . .
C00Q C 0.7792(4) 0.3263(2) 0.82524(19) 0.0362(7) Uani 1 1 d . . . . .
H00Q H 0.876118 0.294576 0.855194 0.043 Uiso 1 1 calc R U . . .
H004 H 0.502(6) 0.465(3) 0.578(3) 0.080(14) 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'
F F 0.0727 0.0534 '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
C00E O003 C00P 116.5(2) . . ?
C006 N004 C007 123.4(2) . . ?
C006 N004 H004 117(2) . . ?
C007 N004 H004 119(3) . . ?
C007 N005 C00I 116.5(2) . . ?
O002 C006 N004 121.5(2) . . ?
O002 C006 C00D 124.1(3) . . ?
N004 C006 C00D 114.3(2) . . ?
N004 C007 C00C 116.7(2) . . ?
N005 C007 N004 123.8(3) . . ?
N005 C007 C00C 119.4(2) . . ?
C00I C008 H008 120.0 . . ?
C00J C008 H008 120.0 . . ?
C00J C008 C00I 120.0(3) . . ?
C00A C009 H009 120.4 . . ?
C00A C009 C00B 119.2(3) . . ?
C00B C009 H009 120.4 . . ?
F001 C00A C00E 117.4(3) . . ?
C009 C00A F001 119.0(3) . . ?
C009 C00A C00E 123.6(3) . . ?
C009 C00B C00L 119.5(3) . . ?
C00M C00B C009 118.1(3) . . ?
C00M C00B C00L 122.2(2) . . ?
C00F C00C C007 118.2(3) . . ?
C00F C00C C00L 120.2(3) . . ?
C00L C00C C007 121.5(3) . . ?
C00I C00D C006 118.3(3) . . ?
C00K C00D C006 120.9(3) . . ?
C00K C00D C00I 120.7(3) . . ?
O003 C00E C00A 116.3(2) . . ?
O003 C00E C00G 126.4(3) . . ?
C00G C00E C00A 117.4(3) . . ?
C00C C00F H00F 119.6 . . ?
C00H C00F C00C 120.7(3) . . ?
C00H C00F H00F 119.6 . . ?
C00E C00G H00G 119.9 . . ?
C00E C00G C00M 120.2(3) . . ?
C00M C00G H00G 119.9 . . ?
C00F C00H H00H 120.4 . . ?
C00Q C00H C00F 119.3(3) . . ?
C00Q C00H H00H 120.4 . . ?
N005 C00I C008 118.4(3) . . ?
N005 C00I C00D 123.2(2) . . ?
C00D C00I C008 118.4(3) . . ?
C008 C00J H00J 119.4 . . ?
C008 C00J C00N 121.2(3) . . ?
C00N C00J H00J 119.4 . . ?
C00D C00K H00K 120.1 . . ?
C00N C00K C00D 119.9(3) . . ?
C00N C00K H00K 120.1 . . ?
C00C C00L C00B 122.3(3) . . ?
C00O C00L C00B 119.1(3) . . ?
C00O C00L C00C 118.2(3) . . ?
C00B C00M C00G 121.5(3) . . ?
C00B C00M H00M 119.3 . . ?
C00G C00M H00M 119.3 . . ?
C00J C00N H00N 120.1 . . ?
C00K C00N C00J 119.8(3) . . ?
C00K C00N H00N 120.1 . . ?
C00L C00O H00O 119.4 . . ?
C00Q C00O C00L 121.2(3) . . ?
C00Q C00O H00O 119.4 . . ?
O003 C00P H00A 109.5 . . ?
O003 C00P H00B 109.5 . . ?
O003 C00P H00C 109.5 . . ?
H00A C00P H00B 109.5 . . ?
H00A C00P H00C 109.5 . . ?
H00B C00P H00C 109.5 . . ?
C00H C00Q H00Q 119.8 . . ?
C00O C00Q C00H 120.3(3) . . ?
C00O C00Q H00Q 119.8 . . ?
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
F001 C00A 1.363(3) . ?
O002 C006 1.233(3) . ?
O003 C00E 1.359(3) . ?
O003 C00P 1.430(4) . ?
N004 C006 1.375(4) . ?
N004 C007 1.379(4) . ?
N004 H004 1.03(5) . ?
N005 C007 1.303(3) . ?
N005 C00I 1.390(4) . ?
C006 C00D 1.458(4) . ?
C007 C00C 1.489(4) . ?
C008 H008 0.9500 . ?
C008 C00I 1.409(4) . ?
C008 C00J 1.374(4) . ?
C009 H009 0.9500 . ?
C009 C00A 1.363(4) . ?
C009 C00B 1.411(4) . ?
C00A C00E 1.395(4) . ?
C00B C00L 1.484(4) . ?
C00B C00M 1.395(4) . ?
C00C C00F 1.393(4) . ?
C00C C00L 1.404(4) . ?
C00D C00I 1.407(4) . ?
C00D C00K 1.395(4) . ?
C00E C00G 1.391(4) . ?
C00F H00F 0.9500 . ?
C00F C00H 1.388(4) . ?
C00G H00G 0.9500 . ?
C00G C00M 1.396(4) . ?
C00H H00H 0.9500 . ?
C00H C00Q 1.387(5) . ?
C00J H00J 0.9500 . ?
C00J C00N 1.392(4) . ?
C00K H00K 0.9500 . ?
C00K C00N 1.379(4) . ?
C00L C00O 1.396(4) . ?
C00M H00M 0.9500 . ?
C00N H00N 0.9500 . ?
C00O H00O 0.9500 . ?
C00O C00Q 1.386(4) . ?
C00P H00A 0.9800 . ?
C00P H00B 0.9800 . ?
C00P H00C 0.9800 . ?
C00Q H00Q 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
F001 C00A C00E O003 0.9(4) . . . . ?
F001 C00A C00E C00G -179.8(3) . . . . ?
O002 C006 C00D C00I -175.1(3) . . . . ?
O002 C006 C00D C00K 6.6(5) . . . . ?
O003 C00E C00G C00M 179.7(3) . . . . ?
N004 C006 C00D C00I 4.6(4) . . . . ?
N004 C006 C00D C00K -173.8(3) . . . . ?
N004 C007 C00C C00F 118.0(3) . . . . ?
N004 C007 C00C C00L -61.8(4) . . . . ?
N005 C007 C00C C00F -59.7(4) . . . . ?
N005 C007 C00C C00L 120.4(3) . . . . ?
C006 N004 C007 N005 0.0(5) . . . . ?
C006 N004 C007 C00C -177.6(3) . . . . ?
C006 C00D C00I N005 -0.4(4) . . . . ?
C006 C00D C00I C008 179.6(3) . . . . ?
C006 C00D C00K C00N 178.1(3) . . . . ?
C007 N004 C006 O002 175.1(3) . . . . ?
C007 N004 C006 C00D -4.6(4) . . . . ?
C007 N005 C00I C008 175.8(3) . . . . ?
C007 N005 C00I C00D -4.2(4) . . . . ?
C007 C00C C00F C00H -178.1(2) . . . . ?
C007 C00C C00L C00B -10.6(4) . . . . ?
C007 C00C C00L C00O 176.5(3) . . . . ?
C008 C00J C00N C00K -1.5(5) . . . . ?
C009 C00A C00E O003 -178.7(3) . . . . ?
C009 C00A C00E C00G 0.6(4) . . . . ?
C009 C00B C00L C00C -51.1(4) . . . . ?
C009 C00B C00L C00O 121.8(3) . . . . ?
C009 C00B C00M C00G 0.5(4) . . . . ?
C00A C009 C00B C00L -174.7(3) . . . . ?
C00A C009 C00B C00M 0.6(4) . . . . ?
C00A C00E C00G C00M 0.5(4) . . . . ?
C00B C009 C00A F001 179.3(3) . . . . ?
C00B C009 C00A C00E -1.2(5) . . . . ?
C00B C00L C00O C00Q -171.3(3) . . . . ?
C00C C00F C00H C00Q 1.4(4) . . . . ?
C00C C00L C00O C00Q 1.8(4) . . . . ?
C00D C00K C00N C00J 1.9(5) . . . . ?
C00E C00G C00M C00B -1.0(4) . . . . ?
C00F C00C C00L C00B 169.6(3) . . . . ?
C00F C00C C00L C00O -3.4(4) . . . . ?
C00F C00H C00Q C00O -2.9(4) . . . . ?
C00I N005 C007 N004 4.5(4) . . . . ?
C00I N005 C007 C00C -178.0(3) . . . . ?
C00I C008 C00J C00N -0.8(5) . . . . ?
C00I C00D C00K C00N -0.2(4) . . . . ?
C00J C008 C00I N005 -177.5(3) . . . . ?
C00J C008 C00I C00D 2.5(4) . . . . ?
C00K C00D C00I N005 177.9(3) . . . . ?
C00K C00D C00I C008 -2.0(4) . . . . ?
C00L C00B C00M C00G 175.7(3) . . . . ?
C00L C00C C00F C00H 1.8(4) . . . . ?
C00L C00O C00Q C00H 1.3(5) . . . . ?
C00M C00B C00L C00C 133.8(3) . . . . ?
C00M C00B C00L C00O -53.3(4) . . . . ?
C00P O003 C00E C00A 172.7(3) . . . . ?
C00P O003 C00E C00G -6.6(4) . . . . ?
