 
data_2008lsh115
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
N,N'-bis(3-Fluorophenyl)urea
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C13 H10 F2 N2 O'
_chemical_formula_weight          248.23
 
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'
 'F'  'F'   0.0171   0.0103
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            Monoclinic
_symmetry_space_group_name_H-M    C2/c
 
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'
 '-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                    20.7183(7)
_cell_length_b                    12.6104(5)
_cell_length_c                    9.1726(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  109.300(2)
_cell_angle_gamma                 90.00
_cell_volume                      2261.81(14)
_cell_formula_units_Z             8
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     14167
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        'cut lath'
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.26
_exptl_crystal_size_mid           0.08
_exptl_crystal_size_min           0.02
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.458
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1024
_exptl_absorpt_coefficient_mu     0.117
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.9702
_exptl_absorpt_correction_T_max   0.9977
_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 0.858081. 
;
 
_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             13299
_diffrn_reflns_av_R_equivalents   0.0516
_diffrn_reflns_av_sigmaI/netI     0.0416
_diffrn_reflns_limit_h_min        -25
_diffrn_reflns_limit_h_max        26
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        -11
_diffrn_reflns_limit_l_max        11
_diffrn_reflns_theta_min          3.23
_diffrn_reflns_theta_max          27.49
_reflns_number_total              2586
_reflns_number_gt                 1993
_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.

One of the phenyl rings is disordered over two positions with a freely 
refined ratio of 80%:20%. The geometry and ADPs of the minor part were
constrained to those of the major component. 
The N-H distances were restrained with DFIX 0.88 0.02. 
;
 
_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)+(0.0237P)²+5.0658P] 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      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          2586
_refine_ls_number_parameters      199
_refine_ls_number_restraints      17
_refine_ls_R_factor_all           0.0835
_refine_ls_R_factor_gt            0.0595
_refine_ls_wR_factor_ref          0.1270
_refine_ls_wR_factor_gt           0.1137
_refine_ls_goodness_of_fit_ref    1.107
_refine_ls_restrained_S_all       1.105
_refine_ls_shift/su_max           0.011
_refine_ls_shift/su_mean          0.001
 
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
C7 C 0.12575(10) 0.98648(17) 0.2253(2) 0.0224(4) Uani 1 1 d . A .
C8 C 0.07239(10) 1.16365(17) 0.1845(2) 0.0243(4) Uani 1 1 d . A .
C9 C 0.08852(12) 1.26324(18) 0.2508(2) 0.0297(5) Uani 1 1 d . . .
H9 H 0.1194 1.2711 0.3530 0.036 Uiso 1 1 calc R . .
C10 C 0.05861(13) 1.35044(18) 0.1646(3) 0.0362(6) Uani 1 1 d . . .
C11 C 0.01380(13) 1.3439(2) 0.0159(3) 0.0371(6) Uani 1 1 d . . .
H11 H -0.0060 1.4057 -0.0405 0.045 Uiso 1 1 calc R . .
C12 C -0.00122(12) 1.24445(19) -0.0483(3) 0.0329(5) Uani 1 1 d . . .
H12 H -0.0317 1.2375 -0.1511 0.040 Uiso 1 1 calc R . .
C13 C 0.02734(11) 1.15415(18) 0.0343(2) 0.0284(5) Uani 1 1 d . . .
H13 H 0.0162 1.0861 -0.0115 0.034 Uiso 1 1 calc R . .
N1 N 0.14831(10) 0.90955(15) 0.3347(2) 0.0255(4) Uani 1 1 d D . .
N2 N 0.10028(10) 1.07341(15) 0.2759(2) 0.0264(4) Uani 1 1 d D . .
O1 O 0.12757(8) 0.97857(12) 0.09258(15) 0.0269(3) Uani 1 1 d . . .
C1A C 0.1723(3) 0.8062(5) 0.3164(9) 0.0206(11) Uani 0.800(4) 1 d PD A 1
C2A C 0.1991(5) 0.7787(7) 0.2008(11) 0.0273(11) Uani 0.800(4) 1 d PD A 1
H2A H 0.2061 0.8302 0.1319 0.033 Uiso 0.800(4) 1 calc PR A 1
C3A C 0.2152(3) 0.6718(3) 0.1907(7) 0.0282(10) Uani 0.800(4) 1 d PD A 1
C4A C 0.2089(4) 0.5948(4) 0.2899(10) 0.0293(10) Uani 0.800(4) 1 d PD A 1
H4A H 0.2217 0.5235 0.2806 0.035 Uiso 0.800(4) 1 calc PR A 1
C5A C 0.1826(4) 0.6254(5) 0.4055(8) 0.0283(10) Uani 0.800(4) 1 d PD A 1
H5A H 0.1765 0.5739 0.4754 0.034 Uiso 0.800(4) 1 calc PR A 1
C6A C 0.1654(4) 0.7292(5) 0.4192(8) 0.0244(11) Uani 0.800(4) 1 d PD A 1
H6A H 0.1486 0.7488 0.5000 0.029 Uiso 0.800(4) 1 calc PR A 1
F1A F 0.24117(10) 0.64724(15) 0.0759(2) 0.0438(6) Uani 0.800(4) 1 d PD A 1
C1B C 0.1607(18) 0.805(2) 0.302(4) 0.0206(11) Uani 0.200(4) 1 d PD A 2
C2B C 0.159(2) 0.724(2) 0.403(4) 0.0273(11) Uani 0.200(4) 1 d PD A 2
H2B H 0.1374 0.7338 0.4780 0.033 Uiso 0.200(4) 1 calc PR A 2
C3B C 0.1915(19) 0.627(2) 0.392(4) 0.0282(10) Uani 0.200(4) 1 d PD A 2
C4B C 0.2194(19) 0.608(2) 0.281(4) 0.0293(10) Uani 0.200(4) 1 d PD A 2
H4B H 0.2359 0.5398 0.2665 0.035 Uiso 0.200(4) 1 calc PR A 2
C5B C 0.2227(15) 0.6933(19) 0.187(3) 0.0283(10) Uani 0.200(4) 1 d PD A 2
H5B H 0.2478 0.6852 0.1178 0.034 Uiso 0.200(4) 1 calc PR A 2
C6B C 0.192(2) 0.788(3) 0.191(5) 0.0244(11) Uani 0.200(4) 1 d PD A 2
H6B H 0.1915 0.8413 0.1179 0.029 Uiso 0.200(4) 1 calc PR A 2
F1B F 0.1819(4) 0.5558(6) 0.4954(9) 0.049(3) Uani 0.200(4) 1 d PD A 2
F2 F 0.07388(9) 1.44741(12) 0.23117(19) 0.0560(5) Uani 1 1 d . . .
H2N H 0.1072(12) 1.0790(19) 0.374(2) 0.033(7) Uiso 1 1 d D . .
H1N H 0.1436(14) 0.924(2) 0.424(2) 0.044(8) Uiso 1 1 d D . .
 
 
_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
C7 O1 1.234(2) . ?
C7 N1 1.363(3) . ?
C7 N2 1.363(3) . ?
C8 C9 1.387(3) . ?
C8 C13 1.390(3) . ?
C8 N2 1.418(3) . ?
C9 C10 1.376(3) . ?
C9 H9 0.9500 . ?
C10 F2 1.357(3) . ?
C10 C11 1.376(3) . ?
C11 C12 1.377(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
N1 C1B 1.39(3) . ?
N1 C1A 1.425(6) . ?
N1 H1N 0.875(17) . ?
N2 H2N 0.867(16) . ?
C1A C2A 1.393(6) . ?
C1A C6A 1.394(6) . ?
C2A C3A 1.398(7) . ?
C2A H2A 0.9500 . ?
C3A F1A 1.367(6) . ?
C3A C4A 1.367(6) . ?
C4A C5A 1.398(6) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.373(6) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C1B C2B 1.39(2) . ?
C1B C6B 1.39(2) . ?
C2B C3B 1.42(2) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.351(19) . ?
C3B F1B 1.363(18) . ?
C4B C5B 1.391(18) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.355(19) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
 
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
O1 C7 N1 123.64(19) . . ?
O1 C7 N2 122.85(19) . . ?
N1 C7 N2 113.51(17) . . ?
C9 C8 C13 119.8(2) . . ?
C9 C8 N2 118.41(19) . . ?
C13 C8 N2 121.69(19) . . ?
C10 C9 C8 118.3(2) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
F2 C10 C11 118.7(2) . . ?
F2 C10 C9 117.9(2) . . ?
C11 C10 C9 123.3(2) . . ?
C10 C11 C12 117.5(2) . . ?
C10 C11 H11 121.3 . . ?
C12 C11 H11 121.3 . . ?
C11 C12 C13 121.3(2) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C8 119.7(2) . . ?
C12 C13 H13 120.1 . . ?
C8 C13 H13 120.1 . . ?
C7 N1 C1B 123.7(15) . . ?
C7 N1 C1A 127.8(4) . . ?
C1B N1 C1A 9.4(18) . . ?
C7 N1 H1N 114.9(18) . . ?
C1B N1 H1N 119(2) . . ?
C1A N1 H1N 117.1(18) . . ?
C7 N2 C8 124.91(17) . . ?
C7 N2 H2N 118.0(17) . . ?
C8 N2 H2N 116.4(17) . . ?
C2A C1A C6A 119.8(5) . . ?
C2A C1A N1 124.1(6) . . ?
C6A C1A N1 116.0(6) . . ?
C1A C2A C3A 117.0(6) . . ?
C1A C2A H2A 121.5 . . ?
C3A C2A H2A 121.5 . . ?
F1A C3A C4A 120.0(4) . . ?
F1A C3A C2A 115.7(5) . . ?
C4A C3A C2A 124.3(5) . . ?
C3A C4A C5A 117.1(4) . . ?
C3A C4A H4A 121.4 . . ?
C5A C4A H4A 121.4 . . ?
C6A C5A C4A 120.7(5) . . ?
C6A C5A H5A 119.6 . . ?
C4A C5A H5A 119.6 . . ?
C5A C6A C1A 121.0(5) . . ?
C5A C6A H6A 119.5 . . ?
C1A C6A H6A 119.5 . . ?
C2B C1B N1 120(3) . . ?
C2B C1B C6B 119.2(19) . . ?
N1 C1B C6B 118(3) . . ?
C1B C2B C3B 119(2) . . ?
C1B C2B H2B 120.7 . . ?
C3B C2B H2B 120.7 . . ?
C4B C3B F1B 127.7(19) . . ?
C4B C3B C2B 122.1(19) . . ?
F1B C3B C2B 109.8(19) . . ?
C3B C4B C5B 116.9(17) . . ?
C3B C4B H4B 121.5 . . ?
C5B C4B H4B 121.5 . . ?
C6B C5B C4B 123(2) . . ?
C6B C5B H5B 118.5 . . ?
C4B C5B H5B 118.5 . . ?
C5B C6B C1B 120(2) . . ?
C5B C6B H6B 120.2 . . ?
C1B C6B H6B 120.2 . . ?
 
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
N2 H2N O1  0.867(16) 2.041(18) 2.847(2) 154(2) 6_576
N1 H1N O1  0.875(17) 2.085(19) 2.906(2) 156(2) 6_576
 
_diffrn_measured_fraction_theta_max    0.997
_diffrn_reflns_theta_full              27.49
_diffrn_measured_fraction_theta_full   0.997
_refine_diff_density_max    0.245
_refine_diff_density_min   -0.226
_refine_diff_density_rms    0.054
