 
data_2008lsh045
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 N,N'-bis-Phenylurea
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C13 H12 N2 O'
_chemical_formula_weight          212.25
 
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'
 
_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M    'P n a 21'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, z+1/2'
 'x+1/2, -y+1/2, z'
 '-x+1/2, y+1/2, z+1/2'
 
_cell_length_a                    9.0662(3)
_cell_length_b                    10.3420(4)
_cell_length_c                    11.7380(4)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1100.59(7)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     7942
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        'cut needle'
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.48
_exptl_crystal_size_mid           0.06
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.281
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              448
_exptl_absorpt_coefficient_mu     0.083
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9612
_exptl_absorpt_correction_T_max   0.9983
_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 reports the ratio of minimum to maximum apparent 
transmission as 0.814433. 
;
 
_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             9386
_diffrn_reflns_av_R_equivalents   0.0530
_diffrn_reflns_av_sigmaI/netI     0.0550
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_theta_min          2.99
_diffrn_reflns_theta_max          27.49
_reflns_number_total              2433
_reflns_number_gt                 1999
_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 N-H distances were restrained with DFIX 0.88 0.02. 

The absoluet structure could not be determined unambiguously. 
;
 
_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)+(0.0254P)²+0.5368P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.010(2)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    -1(2)
_refine_ls_number_reflns          2433
_refine_ls_number_parameters      154
_refine_ls_number_restraints      3
_refine_ls_R_factor_all           0.0691
_refine_ls_R_factor_gt            0.0500
_refine_ls_wR_factor_ref          0.1075
_refine_ls_wR_factor_gt           0.0976
_refine_ls_goodness_of_fit_ref    1.080
_refine_ls_restrained_S_all       1.079
_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 -0.0321(2) 0.6748(2) 0.9062(2) 0.0259(5) Uani 1 1 d . . .
C2 C 0.0757(3) 0.7465(2) 0.9633(2) 0.0286(5) Uani 1 1 d . . .
H2 H 0.1141 0.8235 0.9307 0.034 Uiso 1 1 calc R . .
C3 C 0.1259(3) 0.7034(3) 1.0682(2) 0.0351(6) Uani 1 1 d . . .
H3 H 0.2012 0.7502 1.1065 0.042 Uiso 1 1 calc R . .
C4 C 0.0677(3) 0.5934(3) 1.1180(3) 0.0416(7) Uani 1 1 d . . .
H4 H 0.1016 0.5656 1.1906 0.050 Uiso 1 1 calc R . .
C5 C -0.0403(3) 0.5243(3) 1.0611(2) 0.0413(7) Uani 1 1 d . . .
H5 H -0.0810 0.4488 1.0950 0.050 Uiso 1 1 calc R . .
C6 C -0.0894(3) 0.5643(2) 0.9552(2) 0.0319(6) Uani 1 1 d . . .
H6 H -0.1625 0.5158 0.9162 0.038 Uiso 1 1 calc R . .
C7 C -0.0115(2) 0.7658(2) 0.7127(2) 0.0229(5) Uani 1 1 d . . .
C8 C -0.0364(3) 0.8451(2) 0.5160(2) 0.0251(5) Uani 1 1 d . . .
C9 C 0.0837(2) 0.9287(2) 0.5108(2) 0.0272(5) Uani 1 1 d . . .
H9 H 0.1296 0.9574 0.5790 0.033 Uiso 1 1 calc R . .
C10 C 0.1362(3) 0.9700(2) 0.4062(2) 0.0322(5) Uani 1 1 d . . .
H10 H 0.2196 1.0255 0.4032 0.039 Uiso 1 1 calc R . .
C11 C 0.0686(3) 0.9313(3) 0.3058(2) 0.0335(6) Uani 1 1 d . . .
H11 H 0.1057 0.9589 0.2341 0.040 Uiso 1 1 calc R . .
C12 C -0.0536(3) 0.8520(3) 0.3117(2) 0.0366(6) Uani 1 1 d . . .
H12 H -0.1026 0.8272 0.2436 0.044 Uiso 1 1 calc R . .
C13 C -0.1056(3) 0.8082(2) 0.4153(2) 0.0317(5) Uani 1 1 d . . .
H13 H -0.1890 0.7527 0.4178 0.038 Uiso 1 1 calc R . .
N1 N -0.0909(2) 0.7171(2) 0.80033(16) 0.0248(5) Uani 1 1 d D . .
N2 N -0.0941(2) 0.7997(2) 0.62005(18) 0.0262(5) Uani 1 1 d D . .
O1 O 0.12384(15) 0.77817(17) 0.71479(16) 0.0298(4) Uani 1 1 d . . .
H1N H -0.1852(19) 0.708(3) 0.791(2) 0.040(8) Uiso 1 1 d D . .
H2N H -0.185(2) 0.772(2) 0.620(2) 0.027(7) Uiso 1 1 d D . .
 
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 0.0205(11) 0.0329(12) 0.0243(12) -0.0022(11) 0.0028(10) 0.0093(10)
C2 0.0239(11) 0.0296(12) 0.0322(13) -0.0018(10) -0.0006(10) 0.0027(10)
C3 0.0309(13) 0.0455(15) 0.0288(13) -0.0049(12) -0.0057(11) 0.0063(12)
C4 0.0458(17) 0.0472(17) 0.0318(15) 0.0093(13) -0.0040(13) 0.0137(14)
C5 0.0450(16) 0.0342(15) 0.0448(16) 0.0119(13) 0.0032(14) 0.0050(13)
C6 0.0297(12) 0.0284(12) 0.0377(14) 0.0017(11) -0.0031(11) 0.0028(10)
C7 0.0179(9) 0.0247(11) 0.0262(11) -0.0048(9) -0.0028(11) 0.0018(9)
C8 0.0221(11) 0.0287(13) 0.0244(11) -0.0010(11) 0.0005(11) 0.0065(9)
C9 0.0236(12) 0.0276(13) 0.0304(12) -0.0022(11) -0.0016(11) -0.0012(10)
C10 0.0305(12) 0.0264(11) 0.0396(14) 0.0049(13) 0.0043(12) 0.0003(10)
C11 0.0413(15) 0.0309(14) 0.0284(15) 0.0035(11) 0.0040(12) 0.0063(12)
C12 0.0385(15) 0.0403(16) 0.0310(15) 0.0008(12) -0.0066(12) -0.0020(12)
C13 0.0288(12) 0.0349(13) 0.0312(13) 0.0000(12) -0.0050(11) -0.0054(10)
N1 0.0150(9) 0.0359(12) 0.0236(11) 0.0023(9) -0.0039(8) 0.0002(9)
N2 0.0167(9) 0.0339(11) 0.0280(11) 0.0002(9) -0.0041(8) -0.0022(9)
O1 0.0149(7) 0.0455(11) 0.0289(8) -0.0011(8) -0.0009(7) -0.0001(7)
 
_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 C6 1.381(3) . ?
C1 C2 1.398(4) . ?
C1 N1 1.421(3) . ?
C2 C3 1.386(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O1 1.234(2) . ?
C7 N1 1.353(3) . ?
C7 N2 1.366(3) . ?
C8 C9 1.392(3) . ?
C8 C13 1.392(4) . ?
C8 N2 1.409(3) . ?
C9 C10 1.384(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
N1 H1N 0.868(17) . ?
N2 H2N 0.868(17) . ?
 
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
C6 C1 C2 120.1(2) . . ?
C6 C1 N1 118.5(2) . . ?
C2 C1 N1 121.3(2) . . ?
C3 C2 C1 119.0(2) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.4(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C1 C6 C5 120.1(2) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
O1 C7 N1 123.5(2) . . ?
O1 C7 N2 122.3(2) . . ?
N1 C7 N2 114.12(17) . . ?
C9 C8 C13 119.1(2) . . ?
C9 C8 N2 122.4(2) . . ?
C13 C8 N2 118.5(2) . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.8(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 118.9(2) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C13 120.9(2) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C12 C13 C8 120.3(2) . . ?
C12 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
C7 N1 C1 125.42(19) . . ?
C7 N1 H1N 117.9(19) . . ?
C1 N1 H1N 116.6(19) . . ?
C7 N2 C8 124.85(19) . . ?
C7 N2 H2N 115.7(18) . . ?
C8 N2 H2N 117.4(18) . . ?
 
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  0.868(17) 1.953(19) 2.775(2) 157(3) 3_465
N2 H2N O1  0.868(17) 2.13(2) 2.902(3) 148(2) 3_465
 
_diffrn_measured_fraction_theta_max    0.992
_diffrn_reflns_theta_full              27.49
_diffrn_measured_fraction_theta_full   0.992
_refine_diff_density_max    0.199
_refine_diff_density_min   -0.202
_refine_diff_density_rms    0.048
