#------------------------------------------------------------------------------
#$Date: 2011-09-10 05:16:28 +0200 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006164.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_2006164
loop_
_publ_author_name
'Chen, W.'
'Yang, J.-X.'
'Bai, Z.-P.'
'Wang, Z.-X.'
'You, X.-Z.'
_publ_section_title
;
N-(n-Butyl)-3,4-dibromomaleimide
;
_journal_issue 5
_journal_name_full 'Acta Crystallographica Section C'
_journal_page_first 631
_journal_page_last 633
_journal_volume 53
_journal_year 1997
_chemical_formula_sum 'C8 H9 Br2 N O2'
_chemical_formula_weight 310.98
_chemical_name_systematic
;
N-(n-butyl)-3,4-dibromomaleimide
;
_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'
_audit_creation_method SHELXL
_cell_angle_alpha 90.00
_cell_angle_beta 111.140(10)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 7.405(2)
_cell_length_b 18.481(2)
_cell_length_c 8.1246(9)
_cell_measurement_reflns_used 25
_cell_measurement_temperature 300(2)
_cell_measurement_theta_max 13
_cell_measurement_theta_min 12
_cell_volume 1037.0(3)
_computing_cell_refinement 'CAD-4 Software'
_computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1988)'
_computing_data_reduction 'XTAL3.0 (Hall & Stewart, 1990)'
_computing_molecular_graphics
'SHELXTL-Plus (Sheldrick, 1987), ORTEP (Johnson, 1965)'
_computing_publication_material SHELXL-93
_computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature 300(2)
_diffrn_measurement_device 'Enraf-Nonius CAD-4'
_diffrn_measurement_method '\w-2\q 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 0.0584
_diffrn_reflns_av_sigmaI/netI 0.0443
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_k_max 21
_diffrn_reflns_limit_k_min 0
_diffrn_reflns_limit_l_max 9
_diffrn_reflns_limit_l_min 0
_diffrn_reflns_number 1964
_diffrn_reflns_theta_max 24.97
_diffrn_reflns_theta_min 2.20
_diffrn_standards_decay_% none
_diffrn_standards_interval_time 60
_diffrn_standards_number 3
_exptl_absorpt_coefficient_mu 7.784
_exptl_absorpt_correction_T_max 0.035
_exptl_absorpt_correction_T_min 0.018
_exptl_absorpt_correction_type '\y scan (North, Phillips & Mathews, 1968)'
_exptl_crystal_colour Colourless
_exptl_crystal_density_diffrn 1.992
_exptl_crystal_description Parallelepiped
_exptl_crystal_F_000 600
_exptl_crystal_size_max 0.57
_exptl_crystal_size_mid 0.50
_exptl_crystal_size_min 0.43
_refine_diff_density_max 0.543
_refine_diff_density_min -0.766
_refine_ls_extinction_coef 'Not refined'
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_all 1.092
_refine_ls_goodness_of_fit_obs 1.150
_refine_ls_hydrogen_treatment 'see below'
_refine_ls_matrix_type full
_refine_ls_number_parameters 118
_refine_ls_number_reflns 1822
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.092
_refine_ls_restrained_S_obs 1.150
_refine_ls_R_factor_all 0.0713
_refine_ls_R_factor_obs 0.0456
_refine_ls_shift/esd_max -0.001
_refine_ls_shift/esd_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0604P)^2^+0.0218P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all 0.1095
_refine_ls_wR_factor_obs 0.0983
_reflns_number_observed 1353
_reflns_number_total 1822
_reflns_observed_criterion >2sigma(I)
_[local]_cod_data_source_file ta1129.cif
_[local]_cod_data_source_block TA1129
_[local]_cod_cif_authors_sg_H-M 'P 21/c'
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_values 1715 2011-07-08 13:25:40Z adriana
;
_cod_original_cell_volume 1037.1(3)
_cod_database_code 2006164
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_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 0.0581(5) 0.0341(4) 0.0512(5) 0.0011(3) 0.0199(3) 0.0064(3)
Br2 0.0520(4) 0.0645(5) 0.0210(3) 0.0020(4) 0.0147(3) 0.0019(3)
O1 0.071(3) 0.055(3) 0.030(3) 0.002(2) 0.029(2) 0.000(2)
O2 0.074(3) 0.038(3) 0.044(3) 0.000(3) 0.019(2) -0.012(2)
N 0.049(3) 0.034(3) 0.025(3) -0.004(3) 0.012(2) 0.005(2)
C1 0.036(3) 0.037(3) 0.024(3) -0.004(3) 0.013(3) 0.003(3)
C2 0.033(3) 0.030(3) 0.027(3) 0.002(3) 0.014(3) 0.006(3)
C3 0.032(3) 0.033(3) 0.023(3) 0.000(3) 0.010(2) 0.004(3)
C4 0.037(4) 0.042(4) 0.031(3) -0.003(3) 0.007(3) 0.002(3)
C5 0.055(4) 0.046(4) 0.042(4) -0.005(3) 0.019(3) 0.017(3)
C6 0.066(5) 0.042(4) 0.031(4) -0.004(4) 0.014(3) 0.008(3)
C7 0.066(5) 0.056(5) 0.046(4) 0.009(4) 0.020(4) 0.011(4)
C8 0.061(5) 0.074(6) 0.068(6) 0.005(5) 0.013(4) 0.001(5)
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 0.73580(10) 1.10605(4) 0.51920(10) 0.0478(3) Uani d . 1 Br
Br2 0.74130(10) 0.96957(4) 0.19415(8) 0.0454(2) Uani d . 1 Br
O1 0.7526(7) 0.9974(3) 0.8377(6) 0.0488(12) Uani d . 1 O
O2 0.7650(7) 0.8259(3) 0.4396(6) 0.0526(13) Uani d . 1 O
N 0.7736(7) 0.8970(3) 0.6774(6) 0.0361(12) Uani d . 1 N
C1 0.7592(8) 0.9700(3) 0.7062(8) 0.0319(13) Uani d . 1 C
C2 0.7478(8) 1.0064(3) 0.5378(8) 0.0294(13) Uani d . 1 C
C3 0.7515(8) 0.9581(3) 0.4220(7) 0.0294(13) Uani d . 1 C
C4 0.7648(8) 0.8841(4) 0.5067(8) 0.038(2) Uani d . 1 C
C5 0.7843(9) 0.8411(4) 0.8086(9) 0.047(2) Uani d . 1 C
H5A 0.7521(9) 0.7947(4) 0.7498(9) 0.057 Uiso calc R 1 H
H5B 0.6889(9) 0.8515(4) 0.8617(9) 0.057 Uiso calc R 1 H
C6 0.9819(9) 0.8364(4) 0.9521(8) 0.047(2) Uani d . 1 C
H6A 1.0215(9) 0.8844(4) 0.9998(8) 0.057 Uiso calc R 1 H
H6B 0.9736(9) 0.8063(4) 1.0469(8) 0.057 Uiso calc R 1 H
C7 1.1319(10) 0.8062(4) 0.8896(10) 0.056(2) Uani d . 1 C
H7A 1.1387(10) 0.8360(4) 0.7937(10) 0.067 Uiso calc R 1 H
H7B 1.0928(10) 0.7580(4) 0.8431(10) 0.067 Uiso calc R 1 H
C8 1.3304(11) 0.8021(4) 1.0309(11) 0.070(2) Uani d . 1 C
H8A 1.4199(11) 0.7822(4) 0.9821(11) 0.106 Uiso calc R 1 H
H8B 1.3260(11) 0.7716(4) 1.1251(11) 0.106 Uiso calc R 1 H
H8C 1.3718(11) 0.8497(4) 1.0757(11) 0.106 Uiso calc 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 0.0033 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
_geom_angle_publ_flag
C4 N C1 111.1(5) y
C4 N C5 125.2(5) y
C1 N C5 123.6(5) y
O1 C1 N 126.5(5) y
O1 C1 C2 128.1(6) y
N C1 C2 105.4(5) y
C3 C2 C1 110.0(5) y
C3 C2 Br1 129.5(5) y
C1 C2 Br1 120.5(4) y
C2 C3 C4 107.7(5) y
C2 C3 Br2 130.1(5) y
C4 C3 Br2 122.2(4) y
O2 C4 N 126.8(6) y
O2 C4 C3 127.5(6) y
N C4 C3 105.7(5) y
N C5 C6 112.7(5) y
C7 C6 C5 113.2(6) y
C6 C7 C8 113.7(6) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C2 1.848(6) y
Br2 C3 1.838(6) y
O1 C1 1.199(7) y
O2 C4 1.206(8) y
N C4 1.386(8) y
N C1 1.379(8) y
N C5 1.466(8) y
C1 C2 1.499(8) y
C2 C3 1.305(8) y
C3 C4 1.518(8) y
C5 C6 1.510(9) y
C6 C7 1.487(9) y
C7 C8 1.506(11) y