 
data_2008lsh144
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 N,N'-bis(2-Bromoyphenyl)urea
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C13 H10 Br2 N2 O'
_chemical_formula_weight          370.05
 
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'
 
_symmetry_cell_setting            Orthorhombic
_symmetry_space_group_name_H-M    'P 21 21 2'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, z'
 '-x+1/2, y+1/2, -z'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    11.5691(4)
_cell_length_b                    11.5772(4)
_cell_length_c                    4.66620(10)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      624.98(3)
_cell_formula_units_Z             2
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     7685
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        needle
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.30
_exptl_crystal_size_mid           0.02
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.966
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              360
_exptl_absorpt_coefficient_mu     6.473
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.2469
_exptl_absorpt_correction_T_max   0.8814
_exptl_absorpt_process_details    
'SADABS 2007/2 (Sheldrick, G.M., 2007)'

 
_exptl_special_details
;
The Tmin and Tmax values above were generated with the
SIZE command in SHELXL and rely entirely on the crystal 
dimensions given. 
SADABS estimates the minimum and maximum transmission
as 0.5416 and 0.7456, respectively. 
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator    '10cm confocal mirrors'
_diffrn_measurement_device_type   
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method          'φ & ω scans'
_diffrn_detector_area_resol_mean   '4096x4096pixels / 62x62mm'
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             7250
_diffrn_reflns_av_R_equivalents   0.0432
_diffrn_reflns_av_sigmaI/netI     0.0335
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        15
_diffrn_reflns_limit_l_min        -6
_diffrn_reflns_limit_l_max        5
_diffrn_reflns_theta_min          3.52
_diffrn_reflns_theta_max          27.48
_reflns_number_total              1415
_reflns_number_gt                 1376
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction         
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'  
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.

The molecule is disordered over two positions with a freely refined ratio of 
87%:13%. Neighbouring molecule form HB chains, and the disorder corresponds
to opposite directions of propagation of these HB chains, so that approximately
1 in 10 chains changes direction. The precession images h0l, h1l, hk0 and hk1 
display streaking between distinct reflections and hence we conclude that the 
disorder is 'randomly' distributed throughout the crystal rather that 
systematically occuring ever 10th layer. 
The thermal parameters of the second component were constrained to match the
first component with EADP. 

The H atoms on the N were added in calculated 
positions. 

The structure is actually a recemic twin and was refined with the TWIN 
and BASF commands. 
;
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
 'calc w=1/[σ²(Fo²)+(0.0140P)²+0.8259P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    0.484(17)
_refine_ls_number_reflns          1415
_refine_ls_number_parameters      105
_refine_ls_number_restraints      22
_refine_ls_R_factor_all           0.0295
_refine_ls_R_factor_gt            0.0276
_refine_ls_wR_factor_ref          0.0597
_refine_ls_wR_factor_gt           0.0588
_refine_ls_goodness_of_fit_ref    1.092
_refine_ls_restrained_S_all       1.084
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_symmetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.0865(3) 0.3064(3) 0.8002(7) 0.0145(7) Uani 0.868(3) 1 d PD A 1
C2 C 0.1886(3) 0.2579(3) 0.6971(7) 0.0153(7) Uani 0.868(3) 1 d PD A 1
C3 C 0.2252(3) 0.1496(3) 0.7911(7) 0.0191(7) Uani 0.868(3) 1 d PD A 1
H3 H 0.2922 0.1150 0.7108 0.023 Uiso 0.868(3) 1 calc PR A 1
C4 C 0.1635(4) 0.0929(3) 1.0012(10) 0.0226(7) Uani 0.868(3) 1 d PD A 1
H4 H 0.1895 0.0204 1.0712 0.027 Uiso 0.868(3) 1 calc PR A 1
C5 C 0.0633(3) 0.1418(3) 1.1102(7) 0.0194(8) Uani 0.868(3) 1 d PD A 1
H5 H 0.0213 0.1028 1.2557 0.023 Uiso 0.868(3) 1 calc PR A 1
C6 C 0.0242(4) 0.2467(4) 1.0092(10) 0.0177(6) Uani 0.868(3) 1 d PD A 1
H6 H -0.0454 0.2786 1.0824 0.021 Uiso 0.868(3) 1 calc PR A 1
C7 C 0.0000 0.5000 0.8444(14) 0.0138(14) Uani 0.868(3) 2 d SPD . 1
N1 N 0.0456(3) 0.4129(3) 0.6849(7) 0.0178(6) Uani 0.868(3) 1 d PD A 1
H1N H 0.0501 0.4229 0.4983 0.021 Uiso 0.868(3) 1 calc PR A 1
O1 O 0.0000 0.5000 1.1093(8) 0.0167(10) Uani 0.868(3) 2 d SPD A 1
Br1 Br 0.28162(4) 0.33864(4) 0.4301(2) 0.02182(14) Uani 0.868(3) 1 d PD A 1
C1B C 0.0876(13) 0.3073(11) 1.195(4) 0.0145(7) Uani 0.132(3) 1 d PGD A 2
C2B C 0.1884(11) 0.2596(11) 1.306(3) 0.0153(7) Uani 0.132(3) 1 d PGD A 2
C3B C 0.2254(13) 0.1516(13) 1.213(4) 0.0191(7) Uani 0.132(3) 1 d PGD A 2
H3B H 0.2943 0.1190 1.2890 0.023 Uiso 0.132(3) 1 calc PR A 2
C4B C 0.1615(17) 0.0913(11) 1.010(4) 0.0226(7) Uani 0.132(3) 1 d PGD A 2
H4B H 0.1867 0.0175 0.9470 0.027 Uiso 0.132(3) 1 calc PR A 2
C5B C 0.0607(16) 0.1390(14) 0.899(4) 0.0194(8) Uani 0.132(3) 1 d PGD A 2
H5B H 0.0170 0.0978 0.7606 0.023 Uiso 0.132(3) 1 calc PR A 2
C6B C 0.0237(13) 0.2470(14) 0.992(4) 0.0177(6) Uani 0.132(3) 1 d PGD A 2
H6B H -0.0452 0.2796 0.9162 0.021 Uiso 0.132(3) 1 calc PR A 2
C7B C 0.0000 0.5000 1.164(9) 0.0138(14) Uani 0.132(3) 2 d SPD . 2
N1B N 0.0477(17) 0.4131(13) 1.316(4) 0.0178(6) Uani 0.132(3) 1 d PD A 2
H1NB H 0.0547 0.4223 1.5029 0.021 Uiso 0.132(3) 1 calc PR A 2
O1B O 0.0000 0.5000 0.901(9) 0.0167(10) Uani 0.132(3) 2 d SPD A 2
Br1B Br 0.2786(3) 0.3442(3) 1.5679(14) 0.0270(10) Uani 0.132(3) 1 d PD A 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_23
 _atom_site_aniso_U_13
 _atom_site_aniso_U_12
C1 0.0177(17) 0.0149(16) 0.0110(16) -0.0012(12) -0.0024(13) 0.0017(13)
C2 0.0166(16) 0.0170(16) 0.0124(15) -0.0035(13) -0.0010(12) -0.0036(13)
C3 0.0198(16) 0.0195(17) 0.0180(15) -0.0054(13) -0.0024(14) 0.0100(16)
C4 0.0287(16) 0.0122(14) 0.027(2) 0.0007(12) -0.0033(14) 0.0022(13)
C5 0.0264(18) 0.0155(17) 0.0164(17) 0.0019(14) -0.0014(14) -0.0056(14)
C6 0.0174(14) 0.0179(14) 0.0177(15) -0.0023(11) 0.0004(11) 0.0013(11)
C7 0.018(3) 0.015(3) 0.008(3) 0.000 0.000 -0.003(2)
N1 0.0256(16) 0.0178(15) 0.0099(14) -0.0016(11) 0.0015(12) 0.0071(12)
O1 0.028(2) 0.0154(18) 0.006(3) 0.000 0.000 0.0080(16)
Br1 0.02165(18) 0.02645(19) 0.0174(3) -0.0017(2) 0.0032(2) -0.00259(18)
C1B 0.0177(17) 0.0149(16) 0.0110(16) -0.0012(12) -0.0024(13) 0.0017(13)
C2B 0.0166(16) 0.0170(16) 0.0124(15) -0.0035(13) -0.0010(12) -0.0036(13)
C3B 0.0198(16) 0.0195(17) 0.0180(15) -0.0054(13) -0.0024(14) 0.0100(16)
C4B 0.0287(16) 0.0122(14) 0.027(2) 0.0007(12) -0.0033(14) 0.0022(13)
C5B 0.0264(18) 0.0155(17) 0.0164(17) 0.0019(14) -0.0014(14) -0.0056(14)
C6B 0.0174(14) 0.0179(14) 0.0177(15) -0.0023(11) 0.0004(11) 0.0013(11)
C7B 0.018(3) 0.015(3) 0.008(3) 0.000 0.000 -0.003(2)
N1B 0.0256(16) 0.0178(15) 0.0099(14) -0.0016(11) 0.0015(12) 0.0071(12)
O1B 0.028(2) 0.0154(18) 0.006(3) 0.000 0.000 0.0080(16)
Br1B 0.0291(15) 0.0281(15) 0.024(3) 0.0051(17) -0.0055(18) -0.0053(15)
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 C2 1.394(5) . ?
C1 C6 1.395(6) . ?
C1 N1 1.426(4) . ?
C2 C3 1.394(5) . ?
C2 Br1 1.893(3) . ?
C3 C4 1.379(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.236(6) . ?
C7 N1 1.360(5) 2_565 ?
C7 N1 1.360(5) . ?
N1 H1N 0.8800 . ?
C1B C2B 1.3900 . ?
C1B C6B 1.3900 . ?
C1B N1B 1.426(14) . ?
C2B C3B 1.3900 . ?
C2B Br1B 1.883(10) . ?
C3B C4B 1.3900 . ?
C3B H3B 0.9500 . ?
C4B C5B 1.3900 . ?
C4B H4B 0.9500 . ?
C5B C6B 1.3900 . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B O1B 1.229(19) . ?
C7B N1B 1.349(18) 2_565 ?
C7B N1B 1.349(18) . ?
N1B H1NB 0.8800 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C2 C1 C6 118.7(3) . . ?
C2 C1 N1 119.9(3) . . ?
C6 C1 N1 121.3(3) . . ?
C1 C2 C3 120.7(3) . . ?
C1 C2 Br1 120.7(3) . . ?
C3 C2 Br1 118.6(3) . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 119.9(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.6(4) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 120.4(4) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O1 C7 N1 123.2(3) . 2_565 ?
O1 C7 N1 123.2(3) . . ?
N1 C7 N1 113.6(5) 2_565 . ?
C7 N1 C1 124.3(3) . . ?
C7 N1 H1N 117.9 . . ?
C1 N1 H1N 117.9 . . ?
C2B C1B C6B 120.0 . . ?
C2B C1B N1B 117.7(11) . . ?
C6B C1B N1B 122.0(11) . . ?
C1B C2B C3B 120.0 . . ?
C1B C2B Br1B 120.0(7) . . ?
C3B C2B Br1B 119.9(7) . . ?
C4B C3B C2B 120.0 . . ?
C4B C3B H3B 120.0 . . ?
C2B C3B H3B 120.0 . . ?
C3B C4B C5B 120.0 . . ?
C3B C4B H4B 120.0 . . ?
C5B C4B H4B 120.0 . . ?
C6B C5B C4B 120.0 . . ?
C6B C5B H5B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
C5B C6B C1B 120.0 . . ?
C5B C6B H6B 120.0 . . ?
C1B C6B H6B 120.0 . . ?
O1B C7B N1B 121.7(15) . 2_565 ?
O1B C7B N1B 121.7(15) . . ?
N1B C7B N1B 117(3) 2_565 . ?
C7B N1B C1B 124.3(16) . . ?
C7B N1B H1NB 117.8 . . ?
C1B N1B H1NB 117.8 . . ?
 
loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_angle_DHA
 _geom_hbond_site_symmetry_A
N1 H1N O1  0.88 2.10 2.917(5) 153.2 1_554
N1B H1NB O1B  0.88 2.16 2.96(3) 150.9 1_556
 
_diffrn_measured_fraction_theta_max    0.999
_diffrn_reflns_theta_full              27.48
_diffrn_measured_fraction_theta_full   0.999
_refine_diff_density_max    0.374
_refine_diff_density_min   -0.372
_refine_diff_density_rms    0.082
