#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/16/7151684.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_7151684
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 H12 N2 O3'
_chemical_formula_weight         280.28
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4710(1)
_cell_length_b                   8.3050(1)
_cell_length_c                   21.1940(4)
_cell_measurement_reflns_used    18039
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     1315.02(3)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0757
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            23576
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.67
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.908
_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    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.156
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.7(12)
_refine_ls_extinction_coef       0.021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3016
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0426
_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)+(0.0568P)²+0.0116P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.1022
_reflns_number_gt                2288
_reflns_number_total             3016
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0OB00665C.TXT
_cod_data_source_block           Compound-26a_k08farm7
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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      P212121
_cod_database_code               7151684
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -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
O1 O 0.22161(19) 0.00894(15) 0.10297(5) 0.0389(3) Uani 1 1 d . . .
O2 O 0.08170(19) -0.06175(16) 0.39575(6) 0.0406(4) Uani 1 1 d . . .
O3 O 0.2203(2) -0.28674(16) 0.41404(6) 0.0493(4) Uani 1 1 d . . .
N1 N 0.3111(2) 0.18029(17) 0.18184(7) 0.0337(4) Uani 1 1 d . . .
N2 N 0.1674(2) -0.17974(18) 0.37832(7) 0.0351(4) Uani 1 1 d . . .
C1 C 0.3446(2) 0.1991(2) 0.24486(8) 0.0326(4) Uani 1 1 d . . .
H1 H 0.3906 0.3004 0.2578 0.039 Uiso 1 1 calc R . .
C2 C 0.3184(2) 0.08647(19) 0.29105(7) 0.0283(4) Uani 1 1 d . . .
C3 C 0.2482(2) -0.0669(2) 0.27139(8) 0.0281(4) Uani 1 1 d . . .
C4 C 0.1990(2) -0.1990(2) 0.31050(8) 0.0298(4) Uani 1 1 d . . .
C5 C 0.1590(2) -0.3483(2) 0.28687(9) 0.0347(4) Uani 1 1 d . . .
H5 H 0.1339 -0.4344 0.3150 0.042 Uiso 1 1 calc R . .
C6 C 0.1548(3) -0.3749(2) 0.22200(9) 0.0369(4) Uani 1 1 d . . .
H6 H 0.1331 -0.4797 0.2058 0.044 Uiso 1 1 calc R . .
C7 C 0.1823(3) -0.2482(2) 0.18186(9) 0.0344(4) Uani 1 1 d . . .
H7 H 0.1701 -0.2635 0.1377 0.041 Uiso 1 1 calc R . .
C8 C 0.2286(2) -0.0953(2) 0.20551(8) 0.0301(4) Uani 1 1 d . . .
C9 C 0.2571(2) 0.0383(2) 0.16407(8) 0.0303(4) Uani 1 1 d . . .
C10 C 0.2624(3) 0.1341(2) 0.05791(9) 0.0441(5) Uani 1 1 d . . .
H10A H 0.1847 0.2272 0.0656 0.066 Uiso 1 1 calc R . .
H10B H 0.2422 0.0936 0.0151 0.066 Uiso 1 1 calc R . .
H10C H 0.3878 0.1665 0.0625 0.066 Uiso 1 1 calc R . .
C11 C 0.3796(2) 0.1265(2) 0.35606(8) 0.0296(4) Uani 1 1 d . . .
C12 C 0.3384(3) 0.2754(2) 0.38230(9) 0.0354(4) Uani 1 1 d . . .
H12 H 0.2623 0.3472 0.3600 0.043 Uiso 1 1 calc R . .
C13 C 0.4063(3) 0.3208(2) 0.44041(9) 0.0407(5) Uani 1 1 d . . .
H13 H 0.3789 0.4239 0.4572 0.049 Uiso 1 1 calc R . .
C14 C 0.5137(3) 0.2162(2) 0.47378(9) 0.0416(5) Uani 1 1 d . . .
H14 H 0.5586 0.2459 0.5141 0.050 Uiso 1 1 calc R . .
C15 C 0.5558(3) 0.0673(2) 0.44818(9) 0.0385(5) Uani 1 1 d . . .
H15 H 0.6298 -0.0050 0.4711 0.046 Uiso 1 1 calc R . .
C16 C 0.4914(3) 0.0232(2) 0.38974(9) 0.0325(4) Uani 1 1 d . . .
H16 H 0.5235 -0.0781 0.3723 0.039 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'
O O 0.0106 0.0060 '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'
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
C9 O1 C10 117.70(13) . . ?
C9 N1 C1 116.26(15) . . ?
O2 N2 O3 123.91(15) . . ?
O2 N2 C4 117.80(14) . . ?
O3 N2 C4 118.18(16) . . ?
N1 C1 C2 126.50(16) . . ?
N1 C1 H1 116.8 . . ?
C2 C1 H1 116.8 . . ?
C1 C2 C3 116.74(15) . . ?
C1 C2 C11 117.76(15) . . ?
C3 C2 C11 125.25(15) . . ?
C4 C3 C8 114.64(15) . . ?
C4 C3 C2 127.43(15) . . ?
C8 C3 C2 117.91(15) . . ?
C5 C4 C3 122.75(16) . . ?
C5 C4 N2 114.95(16) . . ?
C3 C4 N2 121.93(16) . . ?
C4 C5 C6 120.61(17) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C7 C6 C5 119.22(17) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 C8 120.60(17) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C3 121.58(15) . . ?
C7 C8 C9 121.14(16) . . ?
C3 C8 C9 117.27(15) . . ?
N1 C9 O1 120.28(15) . . ?
N1 C9 C8 124.80(16) . . ?
O1 C9 C8 114.91(15) . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 118.36(17) . . ?
C12 C11 C2 120.03(16) . . ?
C16 C11 C2 121.37(16) . . ?
C13 C12 C11 121.12(18) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C14 C13 C12 119.89(17) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 119.58(18) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 120.63(18) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C11 120.39(17) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 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
O1 C9 1.344(2) . ?
O1 C10 1.444(2) . ?
O2 N2 1.2274(19) . ?
O3 N2 1.2325(18) . ?
N1 C9 1.302(2) . ?
N1 C1 1.368(2) . ?
N2 C4 1.465(2) . ?
C1 C2 1.368(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.439(2) . ?
C2 C11 1.489(2) . ?
C3 C4 1.423(2) . ?
C3 C8 1.424(2) . ?
C4 C5 1.370(2) . ?
C5 C6 1.393(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.369(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.408(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.431(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.391(2) . ?
C11 C16 1.394(3) . ?
C12 C13 1.384(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(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 N1 C1 C2 -3.5(3) . . . . ?
N1 C1 C2 C3 -0.1(3) . . . . ?
N1 C1 C2 C11 174.43(17) . . . . ?
C1 C2 C3 C4 -175.71(17) . . . . ?
C11 C2 C3 C4 10.2(3) . . . . ?
C1 C2 C3 C8 6.1(2) . . . . ?
C11 C2 C3 C8 -167.99(15) . . . . ?
C8 C3 C4 C5 8.4(3) . . . . ?
C2 C3 C4 C5 -169.87(17) . . . . ?
C8 C3 C4 N2 -164.39(15) . . . . ?
C2 C3 C4 N2 17.4(3) . . . . ?
O2 N2 C4 C5 -130.60(18) . . . . ?
O3 N2 C4 C5 45.8(2) . . . . ?
O2 N2 C4 C3 42.7(2) . . . . ?
O3 N2 C4 C3 -140.94(18) . . . . ?
C3 C4 C5 C6 -3.8(3) . . . . ?
N2 C4 C5 C6 169.41(16) . . . . ?
C4 C5 C6 C7 -3.2(3) . . . . ?
C5 C6 C7 C8 5.1(3) . . . . ?
C6 C7 C8 C3 0.0(3) . . . . ?
C6 C7 C8 C9 -179.77(17) . . . . ?
C4 C3 C8 C7 -6.4(2) . . . . ?
C2 C3 C8 C7 171.99(16) . . . . ?
C4 C3 C8 C9 173.35(15) . . . . ?
C2 C3 C8 C9 -8.3(2) . . . . ?
C1 N1 C9 O1 -179.79(16) . . . . ?
C1 N1 C9 C8 1.0(3) . . . . ?
C10 O1 C9 N1 6.0(3) . . . . ?
C10 O1 C9 C8 -174.73(15) . . . . ?
C7 C8 C9 N1 -175.39(18) . . . . ?
C3 C8 C9 N1 4.8(3) . . . . ?
C7 C8 C9 O1 5.4(2) . . . . ?
C3 C8 C9 O1 -174.38(14) . . . . ?
C1 C2 C11 C12 46.9(2) . . . . ?
C3 C2 C11 C12 -139.00(18) . . . . ?
C1 C2 C11 C16 -127.37(19) . . . . ?
C3 C2 C11 C16 46.7(3) . . . . ?
C16 C11 C12 C13 0.0(3) . . . . ?
C2 C11 C12 C13 -174.47(17) . . . . ?
C11 C12 C13 C14 -1.4(3) . . . . ?
C12 C13 C14 C15 1.3(3) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C14 C15 C16 C11 -1.4(3) . . . . ?
C12 C11 C16 C15 1.4(3) . . . . ?
C2 C11 C16 C15 175.78(17) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 29434890
2 PubChem 51033612
