#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/73/2237313.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_2237313
loop_
_publ_author_name
'Gou, Gao-Zhang'
'Kou, Jun-Feng'
'Zhou, Qing-Di'
'Chi, Shao-Ming'
_publ_section_title
;
 N-(7-Dibromomethyl-5-methyl-1,8-naphthyridin-2-yl)acetamide--pyrrolidine-2,5-dione
 (1/1)
;
_journal_coeditor_code           GK2541
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o153
_journal_page_last               o154
_journal_paper_doi               10.1107/S1600536812051112
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C12 H11 Br2 N3 O, C4 H5 N O2'
_chemical_formula_moiety         'C12 H11 Br2 N3 O, C4 H5 N O2'
_chemical_formula_sum            'C16 H16 Br2 N4 O3'
_chemical_formula_weight         472.15
_chemical_name_systematic
;
N-(7-Dibromomethyl-5-methyl-1,8-naphthyridin-2-yl)acetamide--
pyrrolidine-2,5-dione (1/1)
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 106.57(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.537(2)
_cell_length_b                   7.0093(14)
_cell_length_c                   11.632(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.99
_cell_measurement_theta_min      3.43
_cell_volume                     901.6(3)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2006)'
_computing_molecular_graphics    'DIAMOND (Brandenburg,1999)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7056
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.43
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.519
_exptl_absorpt_correction_T_max  0.497
_exptl_absorpt_correction_T_min  0.450
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.739
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.724
_refine_diff_density_min         -0.922
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0507
_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)+(0.0757P)²+1.6111P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1642
_reflns_number_gt                1220
_reflns_number_total             1723
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            gk2541.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2237313
_cod_database_fobs_code          2237313
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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_symmetry_multiplicity
C C1 0.5310(7) 0.2500 0.7838(6) 0.0437(17) Uani d S 1 2
C C2 0.4522(7) 0.2500 0.8575(7) 0.0486(18) Uani d S 1 2
H H2A 0.3689 0.2500 0.8226 0.058 Uiso calc SR 1 2
C C3 0.4977(7) 0.2500 0.9803(6) 0.0452(17) Uani d S 1 2
C C4 0.6257(7) 0.2500 1.0284(6) 0.0405(16) Uani d S 1 2
C C5 0.6882(7) 0.2500 1.1520(6) 0.0482(18) Uani d S 1 2
H H5A 0.6446 0.2500 1.2080 0.058 Uiso calc SR 1 2
C C6 0.8109(7) 0.2500 1.1903(7) 0.053(2) Uani d S 1 2
H H6A 0.8518 0.2500 1.2717 0.063 Uiso calc SR 1 2
C C7 0.8749(6) 0.2500 1.1028(6) 0.0456(18) Uani d S 1 2
C C8 0.6974(7) 0.2500 0.9487(6) 0.0415(16) Uani d S 1 2
C C9 0.4859(8) 0.2500 0.6506(7) 0.058(2) Uani d S 1 2
H H9A 0.5554 0.2500 0.6180 0.069 Uiso calc SR 1 2
C C10 0.4146(7) 0.2500 1.0597(7) 0.0491(18) Uani d S 1 2
H H10A 0.3319 0.2500 1.0112 0.074 Uiso d SR 1 2
H H10B 0.4298 0.1382 1.1094 0.074 Uiso d R 1 1
C C11 1.0841(7) 0.2500 1.2427(7) 0.055(2) Uani d S 1 2
C C12 1.2128(7) 0.2500 1.2408(8) 0.067(2) Uani d S 1 2
H H12A 1.2652 0.2500 1.3214 0.101 Uiso d SR 1 2
H H12B 1.2279 0.1382 1.1997 0.101 Uiso d R 1 1
C C13 0.0377(8) 0.2500 0.8080(8) 0.057(2) Uani d S 1 2
C C14 0.0885(8) 0.2500 0.7021(8) 0.069(2) Uani d S 1 2
H H14A 0.1368 0.1384 0.7023 0.082 Uiso d R 1 1
C C15 -0.0232(9) 0.2500 0.5948(8) 0.080(3) Uani d S 1 2
H H15A -0.0251 0.1387 0.5463 0.095 Uiso d R 1 1
C C16 -0.1280(8) 0.2500 0.6435(8) 0.056(2) Uani d S 1 2
N N1 0.6503(6) 0.2500 0.8271(5) 0.0477(15) Uani d S 1 2
N N2 0.8206(6) 0.2500 0.9860(5) 0.0461(15) Uani d S 1 2
N N3 1.0008(6) 0.2500 1.1320(5) 0.0524(16) Uani d S 1 2
H H3A 1.0303 0.2500 1.0719 0.063 Uiso calc SR 1 2
N N4 -0.0857(6) 0.2500 0.7663(5) 0.0502(16) Uani d S 1 2
H H4A -0.1322 0.2500 0.8124 0.060 Uiso calc SR 1 2
O O1 1.0553(6) 0.2500 1.3339(5) 0.093(3) Uani d S 1 2
O O2 0.0955(5) 0.2500 0.9136(5) 0.0759(19) Uani d S 1 2
O O3 -0.2342(6) 0.2500 0.5882(6) 0.081(2) Uani d S 1 2
Br Br1 0.38805(7) 0.02689(12) 0.59139(6) 0.0801(4) Uani d . 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N1 C1 C2 . . 123.1(7)
N1 C1 C9 . . 114.4(6)
C2 C1 C9 . . 122.4(7)
C3 C2 C1 . . 120.5(7)
C3 C2 H2A . . 119.7
C1 C2 H2A . . 119.7
C2 C3 C4 . . 117.1(6)
C2 C3 C10 . . 121.0(7)
C4 C3 C10 . . 121.9(7)
C8 C4 C5 . . 116.5(7)
C8 C4 C3 . . 118.7(6)
C5 C4 C3 . . 124.9(6)
C6 C5 C4 . . 121.0(7)
C6 C5 H5A . . 119.5
C4 C5 H5A . . 119.5
C5 C6 C7 . . 118.2(7)
C5 C6 H6A . . 120.9
C7 C6 H6A . . 120.9
N2 C7 N3 . . 113.9(6)
N2 C7 C6 . . 123.1(7)
N3 C7 C6 . . 123.1(7)
N1 C8 N2 . . 113.6(6)
N1 C8 C4 . . 123.3(7)
N2 C8 C4 . . 123.1(6)
C1 C9 Br1 . . 111.5(3)
C1 C9 Br1 . 4_565 111.5(3)
Br1 C9 Br1 . 4_565 107.7(4)
C1 C9 H9A . . 108.7
Br1 C9 H9A . . 108.7
Br1 C9 H9A 4_565 . 108.7
C3 C10 H10A . . 109.8
C3 C10 H10B . . 109.3
H10A C10 H10B . . 109.5
O1 C11 N3 . . 122.3(8)
O1 C11 C12 . . 122.8(7)
N3 C11 C12 . . 114.9(7)
C11 C12 H12A . . 109.8
C11 C12 H12B . . 109.3
H12A C12 H12B . . 109.5
O2 C13 N4 . . 124.9(8)
O2 C13 C14 . . 126.5(8)
N4 C13 C14 . . 108.6(8)
C13 C14 C15 . . 103.6(7)
C13 C14 H14A . . 111.0
C15 C14 H14A . . 111.0
C16 C15 C14 . . 106.4(7)
C16 C15 H15A . . 110.0
C14 C15 H15A . . 110.8
O3 C16 N4 . . 124.0(8)
O3 C16 C15 . . 127.8(8)
N4 C16 C15 . . 108.2(8)
C1 N1 C8 . . 117.3(6)
C7 N2 C8 . . 118.1(6)
C11 N3 C7 . . 129.2(7)
C11 N3 H3A . . 115.4
C7 N3 H3A . . 115.4
C16 N4 C13 . . 113.2(7)
C16 N4 H4A . . 123.4
C13 N4 H4A . . 123.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N1 . 1.324(9)
C1 C2 . 1.417(10)
C1 C9 . 1.487(10)
C2 C3 . 1.373(10)
C2 H2A . 0.9300
C3 C4 . 1.422(10)
C3 C10 . 1.509(9)
C4 C8 . 1.407(10)
C4 C5 . 1.413(10)
C5 C6 . 1.357(11)
C5 H5A . 0.9300
C6 C7 . 1.418(10)
C6 H6A . 0.9300
C7 N2 . 1.324(9)
C7 N3 . 1.394(9)
C8 N1 . 1.363(9)
C8 N2 . 1.363(9)
C9 Br1 . 1.936(5)
C9 Br1 4_565 1.936(5)
C9 H9A . 0.9800
C10 H10A . 0.9600
C10 H10B . 0.9600
C11 O1 . 1.199(10)
C11 N3 . 1.370(10)
C11 C12 . 1.490(11)
C12 H12A . 0.9600
C12 H12B . 0.9601
C13 O2 . 1.220(10)
C13 N4 . 1.367(10)
C13 C14 . 1.508(12)
C14 C15 . 1.517(13)
C14 H14A . 0.9600
C15 C16 . 1.474(13)
C15 H15A . 0.9600
C16 O3 . 1.210(10)
C16 N4 . 1.372(10)
N3 H3A . 0.8600
N4 H4A . 0.8600
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
C6 H6A O1 . 0.93 2.25 2.838(10) 121
C9 H9A O3 1_655 0.98 2.55 3.507(11) 166
N4 H4A N1 1_455 0.86 2.56 3.317(9) 147
N4 H4A N2 1_455 0.86 2.24 3.045(8) 157
N3 H3A O2 1_655 0.86 2.18 3.038(9) 177
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139085142
