#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/99/2209913.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_2209913
loop_
_publ_author_name
'Bin Chen'
'Yu-quan, Shi'
_publ_section_title
;
 4-Bromo-N-(3-thienylmethyl)-1,8-naphthalimide
;
_journal_coeditor_code           KP2030
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3294
_journal_page_last               o3295
_journal_paper_doi               10.1107/S1600536806025542
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C17 H10 Br N O2 S'
_chemical_formula_moiety         'C17 H10 Br N O2 S'
_chemical_formula_sum            'C17 H10 Br N O2 S'
_chemical_formula_weight         372.23
_chemical_melting_point          468
_chemical_name_systematic
;
4-Bromo-N-(3-thienylmethyl)-1,8-naphthalimide
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 103.721(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4000(16)
_cell_length_b                   7.2252(12)
_cell_length_c                   18.211(2)
_cell_measurement_reflns_used    2957
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.8
_cell_measurement_theta_min      1.8
_cell_volume                     1457.2(4)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'CrystalStructure (Rigaku/MSC, 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0518
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13117
_diffrn_reflns_theta_full        27.83
_diffrn_reflns_theta_max         27.83
_diffrn_reflns_theta_min         1.84
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.970
_exptl_absorpt_correction_T_max  0.7555
_exptl_absorpt_correction_T_min  0.5359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(REQAB; Jacobson, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.003
_refine_diff_density_min         -0.488
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3445
_refine_ls_number_restraints     145
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0509
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0725P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1438
_reflns_number_gt                1897
_reflns_number_total             3445
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp2030.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2209913
_cod_database_fobs_code          2209913
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_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 Br1 0.70639(4) 0.39106(6) -0.09228(3) 0.0747(2) Uani d . 1 . .
O O1 0.1568(3) 0.1254(4) -0.03356(17) 0.0746(9) Uani d . 1 . .
O O2 0.3749(3) 0.0836(4) 0.20873(16) 0.0748(9) Uani d . 1 . .
N N1 0.2665(3) 0.1027(4) 0.08753(17) 0.0510(8) Uani d . 1 A .
C C1 0.2555(4) 0.1378(5) 0.0107(2) 0.0517(10) Uani d D 1 . .
C C2 0.3652(3) 0.1942(5) -0.01211(19) 0.0449(8) Uani d . 1 . .
C C3 0.3606(4) 0.2288(5) -0.0870(2) 0.0584(10) Uani d . 1 . .
H H3A 0.2881 0.2139 -0.1228 0.070 Uiso calc R 1 . .
C C4 0.4635(4) 0.2861(5) -0.1101(2) 0.0583(10) Uani d . 1 . .
H H4A 0.4587 0.3085 -0.1610 0.070 Uiso calc R 1 . .
C C5 0.5701(4) 0.3091(5) -0.0587(2) 0.0550(10) Uani d . 1 . .
C C6 0.5814(3) 0.2746(4) 0.0202(2) 0.0473(9) Uani d . 1 . .
C C7 0.4758(3) 0.2166(4) 0.04166(19) 0.0430(8) Uani d . 1 . .
C C8 0.4816(3) 0.1816(5) 0.1187(2) 0.0458(8) Uani d . 1 . .
C C9 0.5880(4) 0.2066(6) 0.1719(2) 0.0602(10) Uani d . 1 . .
H H9A 0.5908 0.1846 0.2226 0.072 Uiso calc R 1 . .
C C10 0.6917(4) 0.2647(5) 0.1507(2) 0.0676(12) Uani d . 1 . .
H H10A 0.7631 0.2817 0.1873 0.081 Uiso calc R 1 . .
C C11 0.6891(3) 0.2967(5) 0.0765(2) 0.0585(10) Uani d . 1 . .
H H11A 0.7592 0.3335 0.0629 0.070 Uiso calc R 1 . .
C C12 0.3743(4) 0.1190(5) 0.1427(2) 0.0528(10) Uani d . 1 . .
C C17 0.1560(3) 0.0561(6) 0.1127(2) 0.0622(11) Uani d D 1 . .
H H17A 0.1747 -0.0347 0.1523 0.075 Uiso d PR 0.594(6) A 1
H H17B 0.0969 0.0045 0.0712 0.075 Uiso d PR 0.594(6) A 1
H H17C 0.1754 -0.0299 0.1540 0.075 Uiso d PR 0.406(6) A 2
H H17D 0.0985 -0.0012 0.0720 0.075 Uiso d PR 0.406(6) A 2
S S1 0.0610(5) 0.4902(6) 0.2214(2) 0.1033(15) Uani d PDU 0.594(6) A 1
C C13 0.1056(17) 0.2263(15) 0.1417(7) 0.0590(18) Uani d PDU 0.594(6) A 1
C C14 0.1384(11) 0.2956(13) 0.2111(8) 0.074(2) Uani d PDU 0.594(6) A 1
H H14 0.1974 0.2432 0.2497 0.089 Uiso calc PR 0.594(6) A 1
C C15 -0.0044(16) 0.506(2) 0.1259(5) 0.079(3) Uani d PDU 0.594(6) A 1
H H15A -0.0580 0.5972 0.1027 0.095 Uiso calc PR 0.594(6) A 1
C C16 0.0349(11) 0.3639(14) 0.0905(7) 0.068(2) Uani d PDU 0.594(6) A 1
H H16A 0.0188 0.3539 0.0381 0.081 Uiso calc PR 0.594(6) A 1
S S1' -0.0054(8) 0.5270(11) 0.1523(4) 0.102(2) Uani d PDU 0.406(6) A 2
C C13' 0.101(3) 0.229(2) 0.1374(10) 0.061(2) Uani d PDU 0.406(6) A 2
C C14' 0.0145(17) 0.339(2) 0.0995(10) 0.066(3) Uani d PDU 0.406(6) A 2
H H14B -0.0299 0.3167 0.0505 0.080 Uiso calc PR 0.406(6) A 2
C C15' 0.073(2) 0.428(2) 0.2347(8) 0.075(3) Uani d PDU 0.406(6) A 2
H H15B 0.0830 0.4783 0.2828 0.090 Uiso calc PR 0.406(6) A 2
C C16' 0.1182(15) 0.2645(19) 0.2183(10) 0.067(3) Uani d PDU 0.406(6) A 2
H H16B 0.1568 0.1816 0.2553 0.080 Uiso calc PRU 0.406(6) A 2
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'
S S 0.1246 0.1234 '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_publ_flag
C12 N1 C1 124.1(3) yes
C12 N1 C17 117.7(3) yes
C1 N1 C17 118.1(3) yes
O1 C1 N1 119.8(4) ?
O1 C1 C2 123.2(4) ?
N1 C1 C2 117.0(3) ?
C3 C2 C7 119.1(3) ?
C3 C2 C1 119.8(3) ?
C7 C2 C1 121.1(3) ?
C2 C3 C4 121.0(4) ?
C2 C3 H3A 119.5 ?
C4 C3 H3A 119.5 ?
C5 C4 C3 120.4(4) ?
C5 C4 H4A 119.8 ?
C3 C4 H4A 119.8 ?
C4 C5 C6 121.5(4) ?
C4 C5 Br1 119.0(3) ?
C6 C5 Br1 119.5(3) ?
C11 C6 C7 118.9(3) ?
C11 C6 C5 124.4(4) ?
C7 C6 C5 116.6(3) ?
C2 C7 C8 119.6(3) ?
C2 C7 C6 121.4(3) ?
C8 C7 C6 119.0(3) ?
C9 C8 C7 120.2(3) ?
C9 C8 C12 119.3(3) ?
C7 C8 C12 120.4(3) ?
C8 C9 C10 120.7(4) ?
C8 C9 H9A 119.7 ?
C10 C9 H9A 119.7 ?
C11 C10 C9 120.4(4) ?
C11 C10 H10A 119.8 ?
C9 C10 H10A 119.8 ?
C10 C11 C6 120.8(4) ?
C10 C11 H11A 119.6 ?
C6 C11 H11A 119.6 ?
O2 C12 N1 119.1(4) ?
O2 C12 C8 123.1(4) ?
N1 C12 C8 117.7(3) ?
N1 C17 C13 110.3(7) yes
N1 C17 C13' 110.2(10) yes
C13 C17 C13' 3.2(14) ?
N1 C17 H17A 109.6 ?
C13 C17 H17A 109.3 ?
C13' C17 H17A 112.1 ?
N1 C17 H17B 109.6 ?
C13 C17 H17B 109.7 ?
C13' C17 H17B 107.0 ?
H17A C17 H17B 108.3 ?
N1 C17 H17C 109.6 ?
C13 C17 H17C 106.9 ?
C13' C17 H17C 109.7 ?
H17A C17 H17C 2.7 ?
H17B C17 H17C 110.7 ?
N1 C17 H17D 109.6 ?
C13 C17 H17D 112.0 ?
C13' C17 H17D 109.3 ?
H17A C17 H17D 106.0 ?
H17B C17 H17D 2.7 ?
H17C C17 H17D 108.3 ?
C14 S1 C15 93.1(6) ?
C14 C13 C16 109.7(7) ?
C14 C13 C17 126.7(10) yes
C16 C13 C17 121.9(8) yes
C13 C14 S1 112.5(7) ?
C13 C14 H14 123.8 ?
S1 C14 H14 123.8 ?
C16 C15 S1 108.7(10) ?
C16 C15 H15A 125.7 ?
S1 C15 H15A 125.7 ?
C15 C16 C13 114.1(9) ?
C15 C16 H16A 123.0 ?
C13 C16 H16A 123.0 ?
C15' S1' C14' 92.8(9) ?
C14' C13' C16' 108.8(9) ?
C14' C13' C17 130.5(15) yes
C16' C13' C17 118.6(12) yes
C13' C14' S1' 111.4(9) ?
C13' C14' H14B 124.3 ?
S1' C14' H14B 124.3 ?
C16' C15' S1' 108.7(12) ?
C16' C15' H15B 125.7 ?
S1' C15' H15B 125.7 ?
C15' C16' C13' 114.2(11) ?
C15' C16' H16B 122.9 ?
C13' C16' H16B 122.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C5 1.894(4) yes
O1 C1 1.223(5) ?
O2 C12 1.228(5) ?
N1 C12 1.396(5) yes
N1 C1 1.397(5) yes
N1 C17 1.478(5) yes
C1 C2 1.466(5) ?
C2 C3 1.375(5) ?
C2 C7 1.410(5) ?
C3 C4 1.399(5) ?
C3 H3A 0.9300 ?
C4 C5 1.357(5) ?
C4 H4A 0.9300 ?
C5 C6 1.434(5) ?
C6 C11 1.410(5) ?
C6 C7 1.415(5) ?
C7 C8 1.411(5) ?
C8 C9 1.373(5) ?
C8 C12 1.465(5) ?
C9 C10 1.393(6) ?
C9 H9A 0.9300 ?
C10 C11 1.363(5) ?
C10 H10A 0.9300 ?
C11 H11A 0.9300 ?
C17 C13 1.505(7) yes
C17 C13' 1.512(8) yes
C17 H17A 0.9600 ?
C17 H17B 0.9600 ?
C17 H17C 0.9600 ?
C17 H17D 0.9601 ?
S1 C14 1.694(8) yes
S1 C15 1.726(9) yes
C13 C14 1.328(8) yes
C13 C16 1.467(8) yes
C14 H14 0.9300 ?
C15 C16 1.343(9) yes
C15 H15A 0.9300 ?
C16 H16A 0.9300 ?
S1' C15' 1.710(10) yes
S1' C14' 1.711(9) yes
C13' C14' 1.328(9) yes
C13' C16' 1.463(9) yes
C14' H14B 0.9300 ?
C15' C16' 1.349(10) yes
C15' H15B 0.9300 ?
C16' H16B 0.9300 ?
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
C12 N1 C1 O1 -177.8(3)
C17 N1 C1 O1 -1.6(5)
C12 N1 C1 C2 0.3(5)
C17 N1 C1 C2 176.6(3)
O1 C1 C2 C3 -2.6(6)
N1 C1 C2 C3 179.3(3)
O1 C1 C2 C7 176.4(3)
N1 C1 C2 C7 -1.7(5)
C7 C2 C3 C4 -0.2(6)
C1 C2 C3 C4 178.8(3)
C2 C3 C4 C5 -0.2(6)
C3 C4 C5 C6 0.5(6)
C3 C4 C5 Br1 -178.9(3)
C4 C5 C6 C11 -179.7(3)
Br1 C5 C6 C11 -0.3(5)
C4 C5 C6 C7 -0.4(5)
Br1 C5 C6 C7 179.0(2)
C3 C2 C7 C8 180.0(3)
C1 C2 C7 C8 0.9(5)
C3 C2 C7 C6 0.4(5)
C1 C2 C7 C6 -178.7(3)
C11 C6 C7 C2 179.3(3)
C5 C6 C7 C2 -0.1(5)
C11 C6 C7 C8 -0.3(5)
C5 C6 C7 C8 -179.7(3)
C2 C7 C8 C9 -178.6(3)
C6 C7 C8 C9 1.0(5)
C2 C7 C8 C12 1.1(5)
C6 C7 C8 C12 -179.2(3)
C7 C8 C9 C10 -0.7(6)
C12 C8 C9 C10 179.5(3)
C8 C9 C10 C11 -0.3(6)
C9 C10 C11 C6 1.0(6)
C7 C6 C11 C10 -0.7(5)
C5 C6 C11 C10 178.6(3)
C1 N1 C12 O2 -179.4(3)
C17 N1 C12 O2 4.3(5)
C1 N1 C12 C8 1.7(5)
C17 N1 C12 C8 -174.6(3)
C9 C8 C12 O2 -1.5(6)
C7 C8 C12 O2 178.7(3)
C9 C8 C12 N1 177.3(3)
C7 C8 C12 N1 -2.4(5)
C12 N1 C17 C13 80.4(7)
C1 N1 C17 C13 -96.1(7)
C12 N1 C17 C13' 83.8(10)
C1 N1 C17 C13' -92.7(10)
N1 C17 C13 C14 -84.9(15)
C13' C17 C13 C14 -17E1(3)
N1 C17 C13 C16 78.7(15)
C13' C17 C13 C16 -1E1(3)
C16 C13 C14 S1 14.2(16)
C17 C13 C14 S1 179.6(11)
C15 S1 C14 C13 -8.8(13)
C14 S1 C15 C16 0.0(13)
S1 C15 C16 C13 8.1(17)
C14 C13 C16 C15 -14.7(18)
C17 C13 C16 C15 179.2(15)
N1 C17 C13' C14' 95(3)
C13 C17 C13' C14' -17E1(3)
N1 C17 C13' C16' -103.3(18)
C13 C17 C13' C16' -1E1(3)
C16' C13' C14' S1' 22(2)
C17 C13' C14' S1' -175.5(18)
C15' S1' C14' C13' -15.9(19)
C14' S1' C15' C16' 4.5(18)
S1' C15' C16' C13' 7(2)
C14' C13' C16' C15' -19(3)
C17 C13' C16' C15' 176(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139070035
