#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/11/7151130.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_7151130
loop_
_publ_author_name
'Barbeau, Olivier R.'
'Cano-Soumillac, Celine'
'Griffin, Roger J.'
'Hardcastle, Ian R.'
'Smith, Graeme C. M.'
'Richardson, Caroline'
'Clegg, William'
'Harrington, Ross W.'
'Golding, Bernard T.'
_publ_section_title
;
 Quinolinone and pyridopyrimidinone inhibitors of DNA-dependent protein
 kinase
;
_journal_issue                   16
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              2670
_journal_paper_doi               10.1039/b705095j
_journal_volume                  5
_journal_year                    2007
_chemical_formula_moiety         'C17 H22 Br N3 O3'
_chemical_formula_sum            'C17 H22 Br N3 O3'
_chemical_formula_weight         396.29
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.413(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8129(4)
_cell_length_b                   28.2692(13)
_cell_length_c                   7.6955(3)
_cell_measurement_reflns_used    11072
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.95
_cell_measurement_theta_min      2.64
_cell_volume                     1676.78(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device_type  'Bruker SMART 1K CCD diffractometer'
_diffrn_measurement_method       'thin-slice ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0264
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14873
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.96
_diffrn_reflns_theta_min         2.64
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.473
_exptl_absorpt_correction_T_max  0.380
_exptl_absorpt_correction_T_min  0.315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.0027(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4117
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0331
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0412P)²+1.0182P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0827
_reflns_number_gt                3518
_reflns_number_total             4117
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b705095j.txt
_cod_data_source_block           irh13_compound_10a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7151130
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.57306(3) 0.255506(7) 0.39395(3) 0.03337(9) Uani 1 1 d . . .
O1 O 0.42211(16) 0.44547(5) 0.7707(2) 0.0259(3) Uani 1 1 d . . .
O2 O 0.97927(17) 0.51109(5) 0.72915(19) 0.0285(3) Uani 1 1 d . . .
O3 O 0.02472(19) 0.31170(6) 0.9576(2) 0.0320(3) Uani 1 1 d . . .
N1 N 0.3978(2) 0.34447(5) 0.5132(2) 0.0191(3) Uani 1 1 d . . .
N2 N 0.71334(19) 0.45385(5) 0.8232(2) 0.0194(3) Uani 1 1 d . . .
N3 N 0.29626(19) 0.33916(5) 0.7754(2) 0.0181(3) Uani 1 1 d . . .
C1 C 0.6260(2) 0.31928(6) 0.3513(2) 0.0192(4) Uani 1 1 d . . .
C2 C 0.7590(2) 0.32913(7) 0.2567(2) 0.0233(4) Uani 1 1 d . . .
H2 H 0.8216 0.3041 0.2136 0.028 Uiso 1 1 calc R . .
C3 C 0.7993(3) 0.37581(8) 0.2260(3) 0.0248(4) Uani 1 1 d . . .
H3 H 0.8912 0.3828 0.1631 0.030 Uiso 1 1 calc R . .
C4 C 0.7066(3) 0.41224(7) 0.2864(3) 0.0243(4) Uani 1 1 d . . .
H4 H 0.7332 0.4442 0.2629 0.029 Uiso 1 1 calc R . .
C5 C 0.5741(2) 0.40209(7) 0.3816(2) 0.0218(4) Uani 1 1 d . . .
H5 H 0.5107 0.4273 0.4222 0.026 Uiso 1 1 calc R . .
C6 C 0.5326(2) 0.35532(6) 0.4185(2) 0.0173(3) Uani 1 1 d . . .
C7 C 0.4212(2) 0.35255(6) 0.6802(2) 0.0162(3) Uani 1 1 d . . .
C8 C 0.5871(2) 0.37384(6) 0.7793(2) 0.0166(3) Uani 1 1 d . . .
H8A H 0.6852 0.3662 0.7174 0.020 Uiso 1 1 calc R . .
H8B H 0.6122 0.3602 0.8992 0.020 Uiso 1 1 calc R . .
C9 C 0.5675(2) 0.42750(6) 0.7910(2) 0.0167(3) Uani 1 1 d . . .
C10 C 0.8923(2) 0.43678(7) 0.8447(3) 0.0207(4) Uani 1 1 d . . .
H10A H 0.8932 0.4021 0.8274 0.025 Uiso 1 1 calc R . .
H10B H 0.9526 0.4439 0.9653 0.025 Uiso 1 1 calc R . .
C11 C 0.9853(2) 0.46089(8) 0.7107(3) 0.0255(4) Uani 1 1 d . . .
H11A H 1.1077 0.4503 0.7277 0.031 Uiso 1 1 calc R . .
H11B H 0.9299 0.4518 0.5904 0.031 Uiso 1 1 calc R . .
C12 C 0.8032(3) 0.52721(7) 0.7007(3) 0.0283(4) Uani 1 1 d . . .
H12A H 0.7470 0.5186 0.5801 0.034 Uiso 1 1 calc R . .
H12B H 0.8011 0.5621 0.7111 0.034 Uiso 1 1 calc R . .
C13 C 0.7022(3) 0.50544(7) 0.8334(3) 0.0237(4) Uani 1 1 d . . .
H13A H 0.7512 0.5162 0.9537 0.028 Uiso 1 1 calc R . .
H13B H 0.5794 0.5155 0.8074 0.028 Uiso 1 1 calc R . .
C14 C 0.1290(2) 0.32299(7) 0.6789(3) 0.0229(4) Uani 1 1 d . . .
H14A H 0.1477 0.3060 0.5711 0.027 Uiso 1 1 calc R . .
H14B H 0.0539 0.3506 0.6428 0.027 Uiso 1 1 calc R . .
C15 C 0.0403(3) 0.29050(8) 0.7926(3) 0.0304(5) Uani 1 1 d . . .
H15A H -0.0767 0.2824 0.7293 0.036 Uiso 1 1 calc R . .
H15B H 0.1076 0.2608 0.8139 0.036 Uiso 1 1 calc R . .
C16 C 0.1943(3) 0.32182(8) 1.0524(3) 0.0275(4) Uani 1 1 d . . .
H16A H 0.2627 0.2922 1.0698 0.033 Uiso 1 1 calc R . .
H16B H 0.1843 0.3348 1.1699 0.033 Uiso 1 1 calc R . .
C17 C 0.2868(2) 0.35726(7) 0.9524(2) 0.0208(4) Uani 1 1 d . . .
H17A H 0.2234 0.3877 0.9431 0.025 Uiso 1 1 calc R . .
H17B H 0.4054 0.3629 1.0169 0.025 Uiso 1 1 calc R . .
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'
Br Br -0.2901 2.4595 '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 O2 C12 110.35(14) . . ?
C15 O3 C16 109.30(15) . . ?
C6 N1 C7 118.77(15) . . ?
C9 N2 C10 126.97(15) . . ?
C9 N2 C13 120.26(15) . . ?
C10 N2 C13 112.74(14) . . ?
C7 N3 C14 118.05(15) . . ?
C7 N3 C17 123.35(15) . . ?
C14 N3 C17 113.75(14) . . ?
Br1 C1 C2 119.03(14) . . ?
Br1 C1 C6 119.20(13) . . ?
C2 C1 C6 121.76(17) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.33(18) . . ?
H2 C2 C3 120.3 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.39(17) . . ?
H3 C3 C4 119.8 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.92(18) . . ?
H4 C4 C5 120.0 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.17(18) . . ?
H5 C5 C6 119.4 . . ?
N1 C6 C1 120.73(16) . . ?
N1 C6 C5 121.84(17) . . ?
C1 C6 C5 117.37(17) . . ?
N1 C7 N3 119.26(16) . . ?
N1 C7 C8 122.80(16) . . ?
N3 C7 C8 117.84(15) . . ?
C7 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
C7 C8 C9 109.74(14) . . ?
H8A C8 H8B 108.2 . . ?
H8A C8 C9 109.7 . . ?
H8B C8 C9 109.7 . . ?
O1 C9 N2 121.97(17) . . ?
O1 C9 C8 120.09(15) . . ?
N2 C9 C8 117.94(15) . . ?
N2 C10 H10A 109.8 . . ?
N2 C10 H10B 109.8 . . ?
N2 C10 C11 109.29(15) . . ?
H10A C10 H10B 108.3 . . ?
H10A C10 C11 109.8 . . ?
H10B C10 C11 109.8 . . ?
O2 C11 C10 110.58(16) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
O2 C12 H12A 109.4 . . ?
O2 C12 H12B 109.4 . . ?
O2 C12 C13 111.10(16) . . ?
H12A C12 H12B 108.0 . . ?
H12A C12 C13 109.4 . . ?
H12B C12 C13 109.4 . . ?
N2 C13 C12 109.02(16) . . ?
N2 C13 H13A 109.9 . . ?
N2 C13 H13B 109.9 . . ?
C12 C13 H13A 109.9 . . ?
C12 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
N3 C14 H14A 109.5 . . ?
N3 C14 H14B 109.5 . . ?
N3 C14 C15 110.56(17) . . ?
H14A C14 H14B 108.1 . . ?
H14A C14 C15 109.5 . . ?
H14B C14 C15 109.5 . . ?
O3 C15 C14 111.93(17) . . ?
O3 C15 H15A 109.2 . . ?
O3 C15 H15B 109.2 . . ?
C14 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
O3 C16 H16A 109.5 . . ?
O3 C16 H16B 109.5 . . ?
O3 C16 C17 110.56(17) . . ?
H16A C16 H16B 108.1 . . ?
H16A C16 C17 109.5 . . ?
H16B C16 C17 109.5 . . ?
N3 C17 C16 109.95(16) . . ?
N3 C17 H17A 109.7 . . ?
N3 C17 H17B 109.7 . . ?
C16 C17 H17A 109.7 . . ?
C16 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
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
Br1 C1 1.8903(18) . ?
O1 C9 1.230(2) . ?
O2 C11 1.428(3) . ?
O2 C12 1.432(2) . ?
O3 C15 1.427(3) . ?
O3 C16 1.433(3) . ?
N1 C6 1.409(2) . ?
N1 C7 1.289(2) . ?
N2 C9 1.350(2) . ?
N2 C10 1.463(2) . ?
N2 C13 1.464(2) . ?
N3 C7 1.366(2) . ?
N3 C14 1.466(2) . ?
N3 C17 1.468(2) . ?
C1 C2 1.391(3) . ?
C1 C6 1.400(3) . ?
C2 H2 0.950 . ?
C2 C3 1.386(3) . ?
C3 H3 0.950 . ?
C3 C4 1.382(3) . ?
C4 H4 0.950 . ?
C4 C5 1.392(3) . ?
C5 H5 0.950 . ?
C5 C6 1.401(3) . ?
C7 C8 1.517(2) . ?
C8 H8A 0.990 . ?
C8 H8B 0.990 . ?
C8 C9 1.529(2) . ?
C10 H10A 0.990 . ?
C10 H10B 0.990 . ?
C10 C11 1.517(3) . ?
C11 H11A 0.990 . ?
C11 H11B 0.990 . ?
C12 H12A 0.990 . ?
C12 H12B 0.990 . ?
C12 C13 1.519(3) . ?
C13 H13A 0.990 . ?
C13 H13B 0.990 . ?
C14 H14A 0.990 . ?
C14 H14B 0.990 . ?
C14 C15 1.513(3) . ?
C15 H15A 0.990 . ?
C15 H15B 0.990 . ?
C16 H16A 0.990 . ?
C16 H16B 0.990 . ?
C16 C17 1.517(3) . ?
C17 H17A 0.990 . ?
C17 H17B 0.990 . ?
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
Br1 C1 C2 C3 -179.57(14) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
Br1 C1 C6 N1 -1.5(2) . . . . ?
Br1 C1 C6 C5 -179.03(13) . . . . ?
C2 C1 C6 N1 179.69(17) . . . . ?
C2 C1 C6 C5 2.2(3) . . . . ?
C4 C5 C6 N1 -179.38(17) . . . . ?
C4 C5 C6 C1 -1.9(3) . . . . ?
C7 N1 C6 C1 109.7(2) . . . . ?
C7 N1 C6 C5 -72.9(2) . . . . ?
C6 N1 C7 N3 -175.51(16) . . . . ?
C6 N1 C7 C8 0.7(3) . . . . ?
C14 N3 C7 N1 -9.5(2) . . . . ?
C14 N3 C7 C8 174.02(15) . . . . ?
C17 N3 C7 N1 -163.30(17) . . . . ?
C17 N3 C7 C8 20.3(2) . . . . ?
N1 C7 C8 C9 93.8(2) . . . . ?
N3 C7 C8 C9 -89.88(19) . . . . ?
C10 N2 C9 O1 -178.17(17) . . . . ?
C10 N2 C9 C8 1.6(3) . . . . ?
C13 N2 C9 O1 -0.6(3) . . . . ?
C13 N2 C9 C8 179.17(16) . . . . ?
C7 C8 C9 O1 20.2(2) . . . . ?
C7 C8 C9 N2 -159.61(16) . . . . ?
C9 N2 C10 C11 122.8(2) . . . . ?
C13 N2 C10 C11 -55.0(2) . . . . ?
C12 O2 C11 C10 -60.6(2) . . . . ?
N2 C10 C11 O2 57.1(2) . . . . ?
C11 O2 C12 C13 60.4(2) . . . . ?
C9 N2 C13 C12 -123.53(18) . . . . ?
C10 N2 C13 C12 54.4(2) . . . . ?
O2 C12 C13 N2 -56.3(2) . . . . ?
C7 N3 C14 C15 154.94(17) . . . . ?
C17 N3 C14 C15 -48.9(2) . . . . ?
C16 O3 C15 C14 -61.1(2) . . . . ?
N3 C14 C15 O3 53.7(2) . . . . ?
C15 O3 C16 C17 62.5(2) . . . . ?
C7 N3 C17 C16 -154.58(17) . . . . ?
C14 N3 C17 C16 50.6(2) . . . . ?
O3 C16 C17 N3 -57.0(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21188743
2 PubChem 17758715
