#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/47/2224752.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2224752
loop_
_publ_author_name
'Ali, Farukh Iftakhar'
'Babar, Tariq Mahmood'
'Rama, Nasim Hasan'
'Jones, Peter G.'
_publ_section_title
;
 3-(3-Bromobenzyl)isoquinolin-1(2H)-one
;
_journal_coeditor_code           RZ2396
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o16
_journal_paper_doi               10.1107/S1600536809051137
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H12 Br N O'
_chemical_formula_moiety         'C16 H12 Br N O'
_chemical_formula_sum            'C16 H12 Br N O'
_chemical_formula_weight         314.18
_chemical_name_systematic
;
3-(3-Bromobenzyl)isoquinolin-1(2H)-one
;
_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                88.698(6)
_cell_angle_beta                 83.829(6)
_cell_angle_gamma                86.529(6)
_cell_formula_units_Z            2
_cell_length_a                   4.5858(4)
_cell_length_b                   9.4976(7)
_cell_length_c                   14.8296(11)
_cell_measurement_reflns_used    9315
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.5961
_cell_measurement_theta_min      2.9954
_cell_volume                     640.88(9)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3543
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Oxford Diffraction Nova A'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Nova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0130
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9267
_diffrn_reflns_theta_full        72.50
_diffrn_reflns_theta_max         75.78
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    4.283
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.651
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.900
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.900
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0260
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0429P)²+0.8338P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0678
_refine_ls_wR_factor_ref         0.0683
_reflns_number_gt                2586
_reflns_number_total             2642
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            rz2396.cif
_cod_data_source_block           I
_cod_database_code               2224752
_cod_database_fobs_code          2224752
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br 0.41731(5) 0.68583(2) -0.065128(12) 0.03136(9) Uani d . 1 . .
N N 0.2730(3) 0.49455(15) 0.40535(10) 0.0155(3) Uani d . 1 . .
H H01 0.131(5) 0.545(3) 0.4306(17) 0.025(6) Uiso d . 1 . .
O O 0.2033(3) 0.33201(12) 0.51915(8) 0.0187(2) Uani d . 1 . .
C C1 0.3423(4) 0.36850(17) 0.44644(11) 0.0159(3) Uani d . 1 . .
C C2 0.4140(4) 0.54534(17) 0.32544(11) 0.0155(3) Uani d . 1 . .
C C3 0.6381(4) 0.46744(18) 0.28064(11) 0.0168(3) Uani d . 1 . .
H H3 0.7347 0.5018 0.2253 0.020 Uiso calc R 1 . .
C C4 0.7296(4) 0.33229(17) 0.31716(11) 0.0162(3) Uani d . 1 . .
C C5 0.9617(4) 0.24635(19) 0.27310(12) 0.0194(3) Uani d . 1 . .
H H5 1.0630 0.2778 0.2178 0.023 Uiso calc R 1 . .
C C6 1.0421(4) 0.11699(19) 0.30999(12) 0.0216(4) Uani d . 1 . .
H H6 1.1988 0.0603 0.2798 0.026 Uiso calc R 1 . .
C C7 0.8955(4) 0.06803(18) 0.39159(12) 0.0216(4) Uani d . 1 . .
H H7 0.9509 -0.0217 0.4160 0.026 Uiso calc R 1 . .
C C8 0.6701(4) 0.15123(18) 0.43607(12) 0.0190(3) Uani d . 1 . .
H H8 0.5721 0.1192 0.4918 0.023 Uiso calc R 1 . .
C C9 0.5853(4) 0.28290(17) 0.39932(11) 0.0159(3) Uani d . 1 . .
C C10 0.2940(4) 0.68958(18) 0.29851(12) 0.0194(3) Uani d . 1 . .
H H10A 0.3169 0.7560 0.3474 0.023 Uiso calc R 1 . .
H H10B 0.0811 0.6853 0.2937 0.023 Uiso calc R 1 . .
C C11 0.4378(4) 0.74776(17) 0.21028(12) 0.0170(3) Uani d . 1 . .
C C12 0.3752(4) 0.69677(18) 0.12761(12) 0.0201(3) Uani d . 1 . .
H H12 0.2438 0.6235 0.1261 0.024 Uiso calc R 1 . .
C C13 0.5061(4) 0.75386(19) 0.04767(12) 0.0211(3) Uani d . 1 . .
C C14 0.6969(4) 0.8617(2) 0.04693(13) 0.0237(4) Uani d . 1 . .
H H14 0.7836 0.9000 -0.0086 0.028 Uiso calc R 1 . .
C C15 0.7580(4) 0.91238(19) 0.12966(14) 0.0247(4) Uani d . 1 . .
H H15 0.8878 0.9864 0.1309 0.030 Uiso calc R 1 . .
C C16 0.6308(4) 0.85559(18) 0.21038(12) 0.0195(3) Uani d . 1 . .
H H16 0.6758 0.8906 0.2665 0.023 Uiso calc R 1 . .
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'
Br Br -0.6763 1.2805 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N C2 . . 125.36(14) ?
O C1 N . . 120.74(15) ?
O C1 C9 . . 123.72(15) ?
N C1 C9 . . 115.54(15) ?
C3 C2 N . . 119.97(15) ?
C3 C2 C10 . . 126.87(15) ?
N C2 C10 . . 113.15(14) ?
C2 C3 C4 . . 119.66(15) ?
C9 C4 C5 . . 118.38(15) ?
C9 C4 C3 . . 119.57(15) ?
C5 C4 C3 . . 122.06(15) ?
C6 C5 C4 . . 120.36(16) ?
C5 C6 C7 . . 120.90(16) ?
C8 C7 C6 . . 119.53(16) ?
C7 C8 C9 . . 120.25(17) ?
C8 C9 C4 . . 120.57(16) ?
C8 C9 C1 . . 119.53(15) ?
C4 C9 C1 . . 119.89(15) ?
C2 C10 C11 . . 114.88(14) ?
C16 C11 C12 . . 119.00(16) ?
C16 C11 C10 . . 120.36(16) ?
C12 C11 C10 . . 120.63(15) ?
C13 C12 C11 . . 119.41(16) ?
C12 C13 C14 . . 122.10(17) ?
C12 C13 Br . . 119.42(14) ?
C14 C13 Br . . 118.46(13) ?
C13 C14 C15 . . 118.22(16) ?
C14 C15 C16 . . 120.44(17) ?
C15 C16 C11 . . 120.83(17) ?
C1 N H01 . . 117.5(16) ?
C2 N H01 . . 117.1(16) ?
C2 C3 H3 . . 120.2 ?
C4 C3 H3 . . 120.2 ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C5 C6 H6 . . 119.6 ?
C7 C6 H6 . . 119.6 ?
C8 C7 H7 . . 120.2 ?
C6 C7 H7 . . 120.2 ?
C7 C8 H8 . . 119.9 ?
C9 C8 H8 . . 119.9 ?
C2 C10 H10A . . 108.5 ?
C11 C10 H10A . . 108.5 ?
C2 C10 H10B . . 108.5 ?
C11 C10 H10B . . 108.5 ?
H10A C10 H10B . . 107.5 ?
C13 C12 H12 . . 120.3 ?
C11 C12 H12 . . 120.3 ?
C13 C14 H14 . . 120.9 ?
C15 C14 H14 . . 120.9 ?
C16 C15 H15 . . 119.8 ?
C14 C15 H15 . . 119.8 ?
C15 C16 H16 . . 119.6 ?
C11 C16 H16 . . 119.6 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br C13 . 1.8997(18) ?
N C1 . 1.367(2) ?
N C2 . 1.379(2) ?
O C1 . 1.245(2) ?
C1 C9 . 1.463(2) ?
C2 C3 . 1.352(2) ?
C2 C10 . 1.507(2) ?
C3 C4 . 1.438(2) ?
C4 C9 . 1.407(2) ?
C4 C5 . 1.413(2) ?
C5 C6 . 1.379(3) ?
C6 C7 . 1.404(3) ?
C7 C8 . 1.380(3) ?
C8 C9 . 1.403(2) ?
C10 C11 . 1.509(2) ?
C11 C16 . 1.394(2) ?
C11 C12 . 1.393(2) ?
C12 C13 . 1.384(2) ?
C13 C14 . 1.386(3) ?
C14 C15 . 1.390(3) ?
C15 C16 . 1.387(3) ?
N H01 . 0.85(3) ?
C3 H3 . 0.9500 ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 H8 . 0.9500 ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C12 H12 . 0.9500 ?
C14 H14 . 0.9500 ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N H01 O 2_566 0.85(3) 1.96(3) 2.8036(19) 176(2)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N C1 O . . . . 179.43(15) ?
C2 N C1 C9 . . . . -0.6(2) ?
C1 N C2 C3 . . . . 1.0(3) ?
C1 N C2 C10 . . . . -178.22(15) ?
N C2 C3 C4 . . . . -0.5(2) ?
C10 C2 C3 C4 . . . . 178.55(16) ?
C2 C3 C4 C9 . . . . -0.2(2) ?
C2 C3 C4 C5 . . . . 179.80(16) ?
C9 C4 C5 C6 . . . . 0.4(2) ?
C3 C4 C5 C6 . . . . -179.64(16) ?
C4 C5 C6 C7 . . . . 0.1(3) ?
C5 C6 C7 C8 . . . . -0.8(3) ?
C6 C7 C8 C9 . . . . 0.9(3) ?
C7 C8 C9 C4 . . . . -0.4(3) ?
C7 C8 C9 C1 . . . . 178.80(15) ?
C5 C4 C9 C8 . . . . -0.2(2) ?
C3 C4 C9 C8 . . . . 179.78(15) ?
C5 C4 C9 C1 . . . . -179.46(15) ?
C3 C4 C9 C1 . . . . 0.6(2) ?
O C1 C9 C8 . . . . 0.6(3) ?
N C1 C9 C8 . . . . -179.41(15) ?
O C1 C9 C4 . . . . 179.80(15) ?
N C1 C9 C4 . . . . -0.2(2) ?
C3 C2 C10 C11 . . . . 2.2(3) ?
N C2 C10 C11 . . . . -178.69(14) ?
C2 C10 C11 C16 . . . . -106.28(18) ?
C2 C10 C11 C12 . . . . 75.1(2) ?
C16 C11 C12 C13 . . . . 0.1(2) ?
C10 C11 C12 C13 . . . . 178.82(15) ?
C11 C12 C13 C14 . . . . -0.6(3) ?
C11 C12 C13 Br . . . . -179.29(12) ?
C12 C13 C14 C15 . . . . 0.4(3) ?
Br C13 C14 C15 . . . . 179.16(13) ?
C13 C14 C15 C16 . . . . 0.1(3) ?
C14 C15 C16 C11 . . . . -0.6(3) ?
C12 C11 C16 C15 . . . . 0.4(3) ?
C10 C11 C16 C15 . . . . -178.27(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744013
