#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/16/7151685.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_7151685
loop_
_publ_author_name
'Sunderland, Peter T.'
'Dhami, Archana'
'Mahon, Mary F.'
'Jones, Louise A.'
'Tully, Sophie R.'
'Lloyd, Matthew D.'
'Thompson, Andrew S.'
'Javaid, Hashim'
'Martin, Niall M. B.'
'Threadgill, Michael D.'
_publ_section_title
;
 Synthesis of 4-alkyl-, 4-aryl- and
 4-arylamino-5-aminoisoquinolin-1-ones and identification of a new
 PARP-2 selective inhibitor.
;
_journal_issue                   3
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              881
_journal_page_last               891
_journal_paper_doi               10.1039/C0OB00665C
_journal_volume                  9
_journal_year                    2011
_chemical_formula_sum            'C16 H11 Br N2 O3'
_chemical_formula_weight         359.18
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                114.347(2)
_cell_angle_beta                 108.553(2)
_cell_angle_gamma                100.738(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6180(4)
_cell_length_b                   9.9120(4)
_cell_length_c                   10.2260(5)
_cell_measurement_reflns_used    10926
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     701.65(6)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV 1997-2004)'
_computing_data_reduction        'Denzo & Scalepack (Otwinowski, Minor 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97/2 (Sheldrick 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_sigmaI/netI    0.0410
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11401
_diffrn_reflns_theta_full        27.42
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         3.74
_exptl_absorpt_coefficient_mu    2.944
_exptl_absorpt_correction_T_max  0.325
_exptl_absorpt_correction_T_min  0.264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.369
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3168
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0318P)²+0.1879P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0642
_refine_ls_wR_factor_ref         0.0680
_reflns_number_gt                2680
_reflns_number_total             3168
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0OB00665C.TXT
_cod_data_source_block           Compound-33_h09mt1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7151685
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.51013(3) 0.46375(3) 0.74138(3) 0.03080(10) Uani 1 1 d . . .
O1 O -0.1656(2) 0.8535(2) 0.9271(2) 0.0453(4) Uani 1 1 d . . .
O2 O -0.2832(2) 0.6782(2) 0.6743(2) 0.0355(4) Uani 1 1 d . . .
O3 O 0.01223(18) 0.15154(16) 0.72365(17) 0.0253(3) Uani 1 1 d . . .
N1 N -0.1858(2) 0.7289(2) 0.8145(2) 0.0281(4) Uani 1 1 d . . .
N2 N -0.2742(2) 0.1357(2) 0.6495(2) 0.0254(4) Uani 1 1 d . . .
C1 C -0.1067(3) 0.2214(2) 0.7186(2) 0.0218(4) Uani 1 1 d . . .
C2 C -0.0357(3) 0.3915(2) 0.7915(2) 0.0203(4) Uani 1 1 d . . .
C3 C 0.1478(3) 0.4756(2) 0.8662(2) 0.0223(4) Uani 1 1 d . . .
H3 H 0.2256 0.4194 0.8702 0.027 Uiso 1 1 calc R . .
C4 C 0.2143(3) 0.6372(3) 0.9327(3) 0.0264(5) Uani 1 1 d . . .
H4 H 0.3380 0.6936 0.9864 0.032 Uiso 1 1 calc R . .
C5 C 0.0998(3) 0.7193(3) 0.9215(3) 0.0254(4) Uani 1 1 d . . .
H5 H 0.1454 0.8313 0.9656 0.030 Uiso 1 1 calc R . .
C6 C -0.0779(3) 0.6378(2) 0.8468(2) 0.0225(4) Uani 1 1 d . . .
C7 C -0.1549(3) 0.4717(2) 0.7845(2) 0.0196(4) Uani 1 1 d . . .
C8 C -0.3360(3) 0.3761(2) 0.7192(2) 0.0223(4) Uani 1 1 d . . .
C9 C -0.3866(3) 0.2157(3) 0.6543(3) 0.0263(5) Uani 1 1 d . . .
H9 H -0.5084 0.1555 0.6094 0.032 Uiso 1 1 calc R . .
C10 C -0.0555(3) -0.0184(2) 0.6571(3) 0.0301(5) Uani 1 1 d . . .
H10A H -0.1392 -0.0713 0.5427 0.036 Uiso 1 1 calc R . .
H10B H -0.1191 -0.0448 0.7139 0.036 Uiso 1 1 calc R . .
C11 C 0.0941(3) -0.0764(2) 0.6741(3) 0.0256(5) Uani 1 1 d . . .
C12 C 0.2683(3) 0.0219(3) 0.7753(3) 0.0419(6) Uani 1 1 d . . .
H12 H 0.2982 0.1332 0.8387 0.050 Uiso 1 1 calc R . .
C13 C 0.3996(3) -0.0410(3) 0.7850(4) 0.0508(7) Uani 1 1 d . . .
H13 H 0.5189 0.0281 0.8545 0.061 Uiso 1 1 calc R . .
C14 C 0.3597(3) -0.2019(3) 0.6953(3) 0.0359(6) Uani 1 1 d . . .
H14 H 0.4506 -0.2439 0.7025 0.043 Uiso 1 1 calc R . .
C15 C 0.1864(3) -0.3015(3) 0.5950(3) 0.0287(5) Uani 1 1 d . . .
H15 H 0.1571 -0.4130 0.5332 0.034 Uiso 1 1 calc R . .
C16 C 0.0547(3) -0.2388(2) 0.5841(3) 0.0263(5) Uani 1 1 d . . .
H16 H -0.0644 -0.3081 0.5140 0.032 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'
Br Br -0.2901 2.4595 '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
C1 O3 C10 116.21(16) . . ?
O2 N1 O1 124.67(19) . . ?
O2 N1 C6 116.74(17) . . ?
O1 N1 C6 118.47(18) . . ?
C1 N2 C9 116.86(18) . . ?
N2 C1 O3 120.27(18) . . ?
N2 C1 C2 124.43(18) . . ?
O3 C1 C2 115.29(17) . . ?
C7 C2 C3 121.11(18) . . ?
C7 C2 C1 118.05(18) . . ?
C3 C2 C1 120.84(18) . . ?
C4 C3 C2 120.54(19) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.79(19) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 119.77(19) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 123.13(19) . . ?
C5 C6 N1 115.16(18) . . ?
C7 C6 N1 121.18(18) . . ?
C2 C7 C6 115.44(18) . . ?
C2 C7 C8 115.97(18) . . ?
C6 C7 C8 128.57(18) . . ?
C9 C8 C7 120.02(18) . . ?
C9 C8 Br1 116.51(15) . . ?
C7 C8 Br1 122.99(15) . . ?
C8 C9 N2 124.27(19) . . ?
C8 C9 H9 117.9 . . ?
N2 C9 H9 117.9 . . ?
O3 C10 C11 109.23(17) . . ?
O3 C10 H10A 109.8 . . ?
C11 C10 H10A 109.8 . . ?
O3 C10 H10B 109.8 . . ?
C11 C10 H10B 109.8 . . ?
H10A C10 H10B 108.3 . . ?
C12 C11 C16 118.3(2) . . ?
C12 C11 C10 123.78(19) . . ?
C16 C11 C10 117.87(19) . . ?
C11 C12 C13 120.4(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 121.0(2) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 119.2(2) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C14 C15 C16 119.9(2) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 121.1(2) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
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 C8 1.897(2) . ?
O1 N1 1.226(2) . ?
O2 N1 1.223(2) . ?
O3 C1 1.339(2) . ?
O3 C10 1.441(2) . ?
N1 C6 1.467(3) . ?
N2 C1 1.305(3) . ?
N2 C9 1.362(3) . ?
C1 C2 1.436(3) . ?
C2 C7 1.413(3) . ?
C2 C3 1.412(3) . ?
C3 C4 1.367(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.366(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.420(3) . ?
C7 C8 1.430(3) . ?
C8 C9 1.358(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.497(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.381(3) . ?
C11 C16 1.389(3) . ?
C12 C13 1.386(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.376(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(3) . ?
C15 H15 0.9500 . ?
C16 H16 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
C9 N2 C1 O3 177.62(18) . . . . ?
C9 N2 C1 C2 -3.1(3) . . . . ?
C10 O3 C1 N2 -3.1(3) . . . . ?
C10 O3 C1 C2 177.50(17) . . . . ?
N2 C1 C2 C7 -1.8(3) . . . . ?
O3 C1 C2 C7 177.54(17) . . . . ?
N2 C1 C2 C3 178.98(19) . . . . ?
O3 C1 C2 C3 -1.7(3) . . . . ?
C7 C2 C3 C4 -0.5(3) . . . . ?
C1 C2 C3 C4 178.76(19) . . . . ?
C2 C3 C4 C5 -2.5(3) . . . . ?
C3 C4 C5 C6 1.3(3) . . . . ?
C4 C5 C6 C7 2.9(3) . . . . ?
C4 C5 C6 N1 -168.78(18) . . . . ?
O2 N1 C6 C5 119.2(2) . . . . ?
O1 N1 C6 C5 -56.9(3) . . . . ?
O2 N1 C6 C7 -52.7(3) . . . . ?
O1 N1 C6 C7 131.2(2) . . . . ?
C3 C2 C7 C6 4.2(3) . . . . ?
C1 C2 C7 C6 -174.99(17) . . . . ?
C3 C2 C7 C8 -174.44(18) . . . . ?
C1 C2 C7 C8 6.3(3) . . . . ?
C5 C6 C7 C2 -5.5(3) . . . . ?
N1 C6 C7 C2 165.67(18) . . . . ?
C5 C6 C7 C8 172.9(2) . . . . ?
N1 C6 C7 C8 -15.8(3) . . . . ?
C2 C7 C8 C9 -6.4(3) . . . . ?
C6 C7 C8 C9 175.2(2) . . . . ?
C2 C7 C8 Br1 165.49(14) . . . . ?
C6 C7 C8 Br1 -13.0(3) . . . . ?
C7 C8 C9 N2 1.6(3) . . . . ?
Br1 C8 C9 N2 -170.71(17) . . . . ?
C1 N2 C9 C8 3.2(3) . . . . ?
C1 O3 C10 C11 -179.38(17) . . . . ?
O3 C10 C11 C12 16.3(3) . . . . ?
O3 C10 C11 C16 -164.63(18) . . . . ?
C16 C11 C12 C13 0.6(4) . . . . ?
C10 C11 C12 C13 179.7(3) . . . . ?
C11 C12 C13 C14 -0.5(5) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C13 C14 C15 C16 0.6(4) . . . . ?
C14 C15 C16 C11 -0.5(3) . . . . ?
C12 C11 C16 C15 -0.1(3) . . . . ?
C10 C11 C16 C15 -179.3(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 29434898
2 PubChem 51033501
