#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2005095.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_2005095
loop_
_publ_author_name
'Karolak-Wojciechowska, J.'
'Kwiatkowski, W.'
'Obniska, J.'
'Zejc, A.'
_publ_section_title
;
 3-(<i>m</i>-Bromophenyl)-1-(3-methyl-2-pyridyl)pyrrolidin-2,5-dione
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1808
_journal_page_last               1810
_journal_volume                  52
_journal_year                    1996
_chemical_formula_sum            'C16 H13 Br N2 O2'
_chemical_formula_weight         345.19
_chemical_name_systematic
;
 1-(3'-Methyl-2'-pyridyl)-3-(-m-bromophenyl)pyrrolidin-2,5-dione
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                68.960(15)
_cell_angle_beta                 68.300(15)
_cell_angle_gamma                89.180(15)
_cell_formula_units_Z            2
_cell_length_a                   8.6110(10)
_cell_length_b                   9.8480(10)
_cell_length_c                   9.9480(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      55
_cell_measurement_theta_min      10
_cell_volume                     724.71(18)
_computing_cell_refinement       'KUMA Diffraction software'
_computing_data_collection       'KUMA Diffraction software'
_computing_data_reduction
' DATRED (P\`epe, 1979) KUMA Diffraction software'
_computing_molecular_graphics    SHELXL93
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'KUMA KM-4 '
_diffrn_measurement_method       \w--2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3123
_diffrn_reflns_theta_max         80.99
_diffrn_reflns_theta_min         5.17
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 100
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    3.919
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.33
_exptl_absorpt_correction_type
'empirical via \y scans (North, Phillips & Matthews, 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.92
_refine_diff_density_min         -0.97
_refine_ls_extinction_coef       0.0036(4)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.147
_refine_ls_goodness_of_fit_obs   1.135
_refine_ls_hydrogen_treatment    'H atoms: riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2956
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.147
_refine_ls_restrained_S_obs      1.135
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_obs          0.0567
_refine_ls_shift/esd_max         -0.21
_refine_ls_shift/esd_mean        0.062
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
; calc w = 1/[\s^2^(Fo^2^)+(0.059P)^2^+1.4438P] where
P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_wR_factor_all         0.1594
_refine_ls_wR_factor_obs         0.1399
_reflns_number_observed          2362
_reflns_number_total             2956
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    bm1056.cif
_[local]_cod_data_source_block   i22
_[local]_cod_cif_authors_sg_H-M  P-1
_cod_original_cell_volume        724.71(13)
_cod_database_code               2005095
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.0823(2) 0.0809(2) 0.04715(15) -0.0041(2) -0.03222(14) -0.01789(14)
N1 0.0486(11) 0.0452(11) 0.0439(9) 0.0102(9) -0.0233(8) -0.0205(8)
O1 0.0659(14) 0.0843(15) 0.0472(10) 0.0173(12) -0.0172(10) -0.0265(10)
O2 0.0504(11) 0.0743(13) 0.0471(10) 0.0082(10) -0.0203(8) -0.0206(9)
C1 0.0617(14) 0.0442(12) 0.0493(11) 0.0097(12) -0.0329(10) -0.0224(10)
C2 0.064(2) 0.068(2) 0.0636(13) 0.0262(14) -0.0367(11) -0.0427(11)
C3 0.058(2) 0.0574(14) 0.0496(12) 0.0141(13) -0.0277(11) -0.0303(10)
C4 0.0480(13) 0.0471(13) 0.0485(11) 0.0057(11) -0.0271(10) -0.0218(10)
C5 0.0422(13) 0.0501(14) 0.0395(11) 0.0063(11) -0.0167(10) -0.0175(10)
C6 0.054(2) 0.0480(14) 0.0598(15) 0.0088(13) -0.0218(12) -0.0235(12)
C7 0.076(2) 0.050(2) 0.073(2) 0.023(2) -0.028(2) -0.0216(14)
C8 0.058(2) 0.075(2) 0.062(2) 0.025(2) -0.0233(15) -0.020(2)
C9 0.049(2) 0.078(2) 0.0497(14) 0.010(2) -0.0220(12) -0.0219(14)
N2 0.0484(12) 0.0545(13) 0.0530(11) 0.0058(11) -0.0244(9) -0.0211(10)
C10 0.098(2) 0.061(2) 0.119(2) 0.011(2) -0.062(2) -0.047(2)
C11 0.0460(13) 0.0480(13) 0.0495(11) 0.0107(11) -0.0262(10) -0.0260(9)
C12 0.0457(13) 0.0454(13) 0.0496(12) 0.0061(11) -0.0248(10) -0.0214(10)
C13 0.0508(13) 0.0500(14) 0.0426(11) 0.0090(12) -0.0255(10) -0.0179(10)
C14 0.0605(15) 0.0596(15) 0.0608(13) 0.0086(13) -0.0350(11) -0.0317(11)
C15 0.060(2) 0.067(2) 0.061(2) -0.011(2) -0.0248(13) -0.0262(13)
C16 0.061(2) 0.060(2) 0.0494(14) -0.0031(15) -0.0233(12) -0.0192(12)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Br1 0.28296(5) 0.52064(5) 0.94544(4) 0.06972(12) Uani d . 1 Br
N1 0.3552(3) 0.2473(2) 1.6834(3) 0.0432(6) Uani d . 1 N
O1 0.1286(3) 0.1851(3) 1.9173(3) 0.0670(7) Uani d . 1 O
O2 0.5327(3) 0.3474(3) 1.4255(2) 0.0576(6) Uani d . 1 O
C1 0.2535(4) 0.4234(3) 1.5159(3) 0.0469(7) Uani d . 1 C
H1A 0.2932(4) 0.5267(3) 1.4665(3) 0.070 Uiso d R 1 H
C2 0.1357(4) 0.3875(4) 1.6845(4) 0.0566(8) Uani d . 1 C
H2A 0.1377(4) 0.4705(4) 1.7133(4) 0.085 Uiso d R 1 H
H2B 0.0223(4) 0.3598(4) 1.6995(4) 0.085 Uiso d R 1 H
C3 0.1964(4) 0.2619(3) 1.7811(3) 0.0502(7) Uani d . 1 C
C4 0.3998(4) 0.3397(3) 1.5291(3) 0.0442(7) Uani d . 1 C
C5 0.4634(4) 0.1487(3) 1.7373(3) 0.0436(7) Uani d . 1 C
C6 0.4504(4) 0.0080(3) 1.7418(4) 0.0531(8) Uani d . 1 C
C7 0.5630(5) -0.0794(4) 1.7907(4) 0.0673(11) Uani d . 1 C
H7A 0.5613(5) -0.1786(4) 1.7959(4) 0.101 Uiso d R 1 H
C8 0.6748(5) -0.0237(4) 1.8332(4) 0.0668(11) Uani d . 1 C
H8A 0.7535(5) -0.0828(4) 1.8664(4) 0.100 Uiso d R 1 H
C9 0.6727(4) 0.1184(4) 1.8255(4) 0.0588(9) Uani d . 1 C
H9A 0.7489(4) 0.1563(4) 1.8578(4) 0.088 Uiso d R 1 H
N2 0.5704(3) 0.2062(3) 1.7754(3) 0.0503(7) Uani d . 1 N
C10 0.3208(6) -0.0491(4) 1.7010(5) 0.0825(12) Uani d . 1 C
H10A 0.3308(6) -0.1490(4) 1.7105(5) 0.124 Uiso d R 1 H
H10B 0.2108(6) -0.0440(4) 1.7711(5) 0.124 Uiso d R 1 H
H10C 0.3365(6) 0.0108(4) 1.5954(5) 0.124 Uiso d R 1 H
C11 0.1836(3) 0.3779(3) 1.4161(3) 0.0433(6) Uani d . 1 C
C12 0.2497(4) 0.4554(3) 1.2570(3) 0.0440(7) Uani d . 1 C
H12A 0.3373(4) 0.5370(3) 1.2109(3) 0.066 Uiso d R 1 H
C13 0.1896(4) 0.4143(3) 1.1638(3) 0.0455(7) Uani d . 1 C
C14 0.0629(4) 0.2993(3) 1.2267(4) 0.0541(8) Uani d . 1 C
H14A 0.0187(4) 0.2748(3) 1.1615(4) 0.081 Uiso d R 1 H
C15 -0.0017(4) 0.2220(4) 1.3853(4) 0.0616(9) Uani d . 1 C
H15A -0.0892(4) 0.1404(4) 1.4311(4) 0.092 Uiso d R 1 H
C16 0.0585(4) 0.2603(4) 1.4808(4) 0.0566(9) Uani d . 1 C
H16A 0.0135(4) 0.2044(4) 1.5915(4) 0.085 Uiso d R 1 H
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
_geom_angle_publ_flag
C4 N1 C3 113.0(2) yes
C4 N1 C5 123.1(2) yes
C3 N1 C5 123.9(2) yes
C4 C1 C11 108.7(2) ?
C4 C1 C2 103.7(2) ?
C11 C1 C2 116.6(3) ?
C3 C2 C1 106.2(3) ?
O1 C3 N1 123.8(3) ?
O1 C3 C2 129.0(3) ?
N1 C3 C2 107.2(2) ?
O2 C4 N1 124.1(3) ?
O2 C4 C1 127.6(3) ?
N1 C4 C1 108.2(2) ?
N2 C5 C6 126.2(3) ?
N2 C5 N1 114.8(3) ?
C6 C5 N1 119.0(3) ?
C5 C6 C7 115.5(3) ?
C5 C6 C10 122.3(3) ?
C7 C6 C10 122.1(3) ?
C8 C7 C6 119.9(4) ?
C9 C8 C7 118.6(4) ?
N2 C9 C8 123.2(4) ?
C5 N2 C9 116.5(3) ?
C16 C11 C12 119.5(3) ?
C16 C11 C1 121.8(3) ?
C12 C11 C1 118.7(2) ?
C13 C12 C11 119.5(3) ?
C14 C13 C12 121.6(3) ?
C14 C13 Br1 119.4(2) ?
C12 C13 Br1 119.0(2) ?
C15 C14 C13 118.6(3) ?
C14 C15 C16 120.7(3) ?
C11 C16 C15 120.0(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C13 1.887(3) ?
N1 C4 1.379(3) yes
N1 C3 1.395(4) yes
N1 C5 1.438(4) yes
O1 C3 1.200(3) ?
O2 C4 1.205(3) ?
C1 C4 1.517(4) ?
C1 C11 1.522(4) ?
C1 C2 1.515(4) ?
C2 C3 1.492(5) ?
C5 N2 1.319(4) ?
C5 C6 1.375(5) ?
C6 C7 1.393(5) ?
C6 C10 1.497(6) ?
C7 C8 1.375(6) ?
C8 C9 1.374(6) ?
C9 N2 1.329(5) ?
C11 C16 1.381(4) ?
C11 C12 1.375(4) ?
C12 C13 1.386(4) ?
C13 C14 1.374(4) ?
C14 C15 1.370(4) ?
C15 C16 1.393(5) ?