# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Jennifer Swift'
_publ_contact_author_email       JAS2@GEORGETOWN.EDU

_publ_section_title              
;
Halogen/Methyl Exchange in a Series of Isostructural
1,3-bis(m-Dihalophenyl)Ureas
;
loop_
_publ_author_name
'Jennifer Swift'
'Joseph A. Basile'
'Christina Capacci-Daniel'
'Shoaleh Dehghan'
'Rupa Hiremath'
;
A.Sarjeant
;
'Victoria M. Wurster'

# Attachment 'mBrMePU_done.cif'

data_mBrMePU
_database_code_depnum_ccdc_archive 'CCDC 695365'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '1-(m-bromophenyl)-3-(m-tolyl) urea'
_chemical_name_common            mBrMePU
_chemical_melting_point          247.5
_chemical_formula_moiety         'C28 H23 Br2 N4 O2'
_chemical_formula_sum            'C28 H23 Br2 N4 O2'
_chemical_formula_weight         607.32

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_
_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                   14.612(6)
_cell_length_b                   9.5770(16)
_cell_length_c                   4.5572(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     637.7(3)
_cell_formula_units_Z            1

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             305

_exptl_special_details           
;
?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'

_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         ?
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5296
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         4.26
_diffrn_reflns_theta_max         27.60
_diffrn_reflns_resolution_max    0.77
_reflns_number_total             1476
_reflns_number_gt                1343
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Oxford Diffraction CrysAlis CCD'
_computing_cell_refinement       'Oxford Diffraction CrysAlis RED'
_computing_data_reduction        'Oxford Diffraction CrysAlis RED'
_computing_structure_solution    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_structure_refinement  'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_molecular_graphics    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_publication_material  'Sheldrick, G.M. (2000). SHELXTL v6.10.'

_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.
;

_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)+(0.0000P)²+2.1441P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(3)
_refine_ls_number_reflns         1476
_refine_ls_number_parameters     96
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1228
_refine_ls_wR_factor_gt          0.1210
_refine_ls_goodness_of_fit_ref   1.220
_refine_ls_restrained_S_all      1.225
_refine_ls_shift/su_max          0.000
_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
Br1 Br 0.07989(10) 0.64891(14) 0.0545(3) 0.0306(3) Uani 0.50 1 d PD A 1
C8 C 0.1020(12) 0.645(4) 0.096(9) 0.21(3) Uani 0.50 1 d PD A 2
H8A H 0.0931 0.5448 0.1317 0.320 Uiso 0.25 1 calc PR A 2
H8B H 0.0936 0.6648 -0.1127 0.320 Uiso 0.25 1 calc PR A 2
H8C H 0.0572 0.6981 0.2110 0.320 Uiso 0.25 1 calc PR A 2
O1 O 0.5000 0.5000 0.4798(10) 0.0219(11) Uani 1 2 d S . .
N1 N 0.4312(2) 0.5578(4) 0.0523(10) 0.0182(8) Uani 1 1 d . . .
H1N H 0.436(4) 0.525(7) -0.150(17) 0.06(2) Uiso 1 1 d . . .
C1 C 0.5000 0.5000 0.2079(15) 0.0181(14) Uani 1 2 d S . .
C2 C 0.3594(3) 0.6346(5) 0.1719(9) 0.0162(9) Uani 1 1 d . . .
C3 C 0.2704(3) 0.6090(5) 0.0732(12) 0.0204(9) Uani 1 1 d . A .
H3 H 0.2595 0.5394 -0.0712 0.024 Uiso 1 1 calc R . .
C4 C 0.1976(3) 0.6862(5) 0.1880(11) 0.0256(11) Uani 1 1 d D . .
C5 C 0.2116(3) 0.7886(5) 0.3964(12) 0.0273(12) Uani 1 1 d . A .
H5 H 0.1617 0.8406 0.4730 0.033 Uiso 1 1 calc R . .
C6 C 0.3013(3) 0.8139(5) 0.4924(11) 0.0279(12) Uani 1 1 d . . .
H6 H 0.3122 0.8840 0.6359 0.033 Uiso 1 1 calc R A .
C7 C 0.3745(3) 0.7379(5) 0.3804(10) 0.0229(11) Uani 1 1 d . A .
H7 H 0.4349 0.7567 0.4465 0.027 Uiso 1 1 calc R . .

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
Br1 0.0152(4) 0.0366(5) 0.0401(6) 0.0045(6) 0.0012(5) 0.0036(4)
C8 0.09(2) 0.33(6) 0.22(4) -0.19(4) -0.04(2) -0.02(2)
O1 0.022(2) 0.035(3) 0.009(3) 0.000 0.000 0.0071(19)
N1 0.0130(17) 0.0277(19) 0.0137(16) -0.0013(17) -0.0049(17) 0.0035(15)
C1 0.014(3) 0.022(3) 0.018(4) 0.000 0.000 -0.002(2)
C2 0.0170(18) 0.020(2) 0.011(2) 0.0024(19) 0.0006(15) 0.0012(18)
C3 0.018(2) 0.024(2) 0.019(2) 0.002(2) 0.0012(18) 0.0019(16)
C4 0.022(2) 0.028(3) 0.026(3) 0.009(2) 0.008(2) 0.0019(19)
C5 0.027(2) 0.028(2) 0.027(3) 0.006(2) 0.012(2) 0.012(2)
C6 0.033(2) 0.028(3) 0.023(3) -0.003(2) 0.004(2) 0.007(2)
C7 0.020(2) 0.031(3) 0.018(3) 0.001(2) 0.0012(17) 0.0016(19)

_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
Br1 C4 1.859(5) . ?
C8 C4 1.511(11) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
O1 C1 1.239(8) . ?
N1 C1 1.349(5) . ?
N1 C2 1.392(5) . ?
N1 H1N 0.97(7) . ?
C1 N1 1.349(5) 2_665 ?
C2 C7 1.389(6) . ?
C2 C3 1.398(6) . ?
C3 C4 1.397(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(7) . ?
C5 C6 1.402(7) . ?
C5 H5 0.9500 . ?
C6 C7 1.391(6) . ?
C6 H6 0.9500 . ?
C7 H7 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
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1 N1 C2 124.9(4) . . ?
C1 N1 H1N 108(4) . . ?
C2 N1 H1N 126(4) . . ?
O1 C1 N1 121.7(3) . 2_665 ?
O1 C1 N1 121.7(3) . . ?
N1 C1 N1 116.5(6) 2_665 . ?
C7 C2 N1 121.7(4) . . ?
C7 C2 C3 119.5(4) . . ?
N1 C2 C3 118.8(4) . . ?
C4 C3 C2 119.7(4) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 121.4(4) . . ?
C5 C4 C8 120.9(14) . . ?
C3 C4 C8 117.5(14) . . ?
C5 C4 Br1 119.9(4) . . ?
C3 C4 Br1 118.7(4) . . ?
C4 C5 C6 118.5(4) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C7 C6 C5 120.8(5) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C2 C7 C6 120.2(4) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 O1 7.0(5) . . . . ?
C2 N1 C1 N1 -173.0(5) . . . 2_665 ?
C1 N1 C2 C7 45.9(6) . . . . ?
C1 N1 C2 C3 -135.8(4) . . . . ?
C7 C2 C3 C4 -0.9(7) . . . . ?
N1 C2 C3 C4 -179.2(4) . . . . ?
C2 C3 C4 C5 0.5(7) . . . . ?
C2 C3 C4 C8 -174(2) . . . . ?
C2 C3 C4 Br1 -179.5(4) . . . . ?
C3 C4 C5 C6 -0.1(7) . . . . ?
C8 C4 C5 C6 174(2) . . . . ?
Br1 C4 C5 C6 179.9(4) . . . . ?
C4 C5 C6 C7 0.0(8) . . . . ?
N1 C2 C7 C6 179.1(5) . . . . ?
C3 C2 C7 C6 0.8(7) . . . . ?
C5 C6 C7 C2 -0.4(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.60
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.086

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 2'
_symmetry_int_tables_number      18
_symmetry_space_group_name_Hall  'P 2 2ab'

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-11.00 11.00 0.00 0.0281
-10.00 -12.00 0.00 0.0127
13.00 -10.00 0.00 0.0279
2.00 3.00 6.00 0.2403
19.00 5.00 0.00 0.0329
7.00 13.00 0.00 0.0269
2.00 1.00 -6.00 0.2424
-20.00 3.00 0.00 0.0326
_audit_creation_date             
;
'Wed Nov 01 11:40:40 2006'
;
_audit_creation_method_reference 
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET)
(compiled Jun 12 2006,17:01:16)
;
_computing_data_collection_reference 
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET)
(compiled Jun 12 2006,17:01:16)
;
_computing_cell_refinment_reference 
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET)
(compiled Jun 12 2006,17:01:16)
;
_computing_data_reduction_reference 
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET)
(compiled Jun 12 2006,17:01:16)
;
_cell_measurement_temperature    110
_cell_measurement_reflns_used    3368
_cell_measurement_theta_min      4.1699
_cell_measurement_theta_max      27.4991
_cell_measurement_resolution_max 0.77
_exptl_crystal_size_max          0.2424
_exptl_crystal_size_mid          0.0805
_exptl_crystal_size_min          0.0127
_exptl_absorpt_coefficient_mu    3.212
_exptl_absorpt_correction_T_min  0.475
_exptl_absorpt_correction_T_max  0.888
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET)
(compiled Jun 12 2006,17:01:16)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 15.9890
_diffrn_orient_matrix_UB_11      -0.0408943476
_diffrn_orient_matrix_UB_12      -0.0697893338
_diffrn_orient_matrix_UB_13      0.0097873498
_diffrn_orient_matrix_UB_21      -0.0024384520
_diffrn_orient_matrix_UB_22      0.0158965117
_diffrn_orient_matrix_UB_23      0.0473556473
_diffrn_orient_matrix_UB_31      -0.1499387900
_diffrn_orient_matrix_UB_32      0.0187449249
_diffrn_orient_matrix_UB_33      -0.0034363117
_diffrn_measurement_details      'see scan set'

_diffrn_measurement_method       ' omega phi scans'

_diffrn_source_power             2
_diffrn_source_voltage           50
_diffrn_source_current           40
_diffrn_measurement_device       Kappa
_diffrn_measurement_device_type  Xcalibur3
_diffrn_ambient_temperature      110
_exptl_crystal_recrystallization_method benzene

#===END

# Attachment 'mBrPU_done.cif'

data_mbrpu
_database_code_depnum_ccdc_archive 'CCDC 695366'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '1,3-bis(m-bromophenyl) urea'
_chemical_name_common            mBrPU
_chemical_melting_point          273.9
_chemical_formula_moiety         'C13 H10 Br2 N2 O'
_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'

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                   9.5460(11)
_cell_length_b                   14.7549(15)
_cell_length_c                   4.5585(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     642.07(14)
_cell_formula_units_Z            2

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.914
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360

_exptl_special_details           
;
?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'

_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         ?
_diffrn_standards_interval_count 1
_diffrn_standards_interval_time  50
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8169
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         4.27
_diffrn_reflns_theta_max         29.08
_diffrn_reflns_resolution_max    0.73
_reflns_number_total             1717
_reflns_number_gt                1661
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Oxford Diffraction CrysAlis CCD'
_computing_cell_refinement       'Oxford Diffraction CrysAlis RED'
_computing_data_reduction        'Oxford Diffraction CrysAlis RED'
_computing_structure_solution    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_structure_refinement  'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_molecular_graphics    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_publication_material  'Sheldrick, G.M. (2000). SHELXTL v6.10.'

_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.
;

_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)+(0.0167P)²+1.6883P] 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   -0.022(17)
_refine_ls_number_reflns         1717
_refine_ls_number_parameters     83
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0686
_refine_ls_wR_factor_gt          0.0676
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_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
Br1 Br 0.84972(4) 0.08145(2) 0.44065(9) 0.02795(11) Uani 1 1 d . . .
O1 O 1.0000 0.5000 0.0189(7) 0.0208(8) Uani 1 2 d S . .
N1 N 0.9435(3) 0.43085(17) 0.4511(6) 0.0136(5) Uani 1 1 d . . .
H1A H 0.9574 0.4304 0.6419 0.016 Uiso 1 1 calc R . .
C1 C 1.0000 0.5000 0.2917(10) 0.0142(9) Uani 1 2 d S . .
C2 C 0.8641(4) 0.36001(19) 0.3264(6) 0.0130(6) Uani 1 1 d . . .
C3 C 0.8896(3) 0.2717(2) 0.4257(8) 0.0152(6) Uani 1 1 d . . .
H3A H 0.9592 0.2604 0.5700 0.018 Uiso 1 1 calc R . .
C4 C 0.8115(4) 0.2010(2) 0.3101(8) 0.0188(7) Uani 1 1 d . . .
C5 C 0.7081(4) 0.2147(2) 0.0983(8) 0.0191(7) Uani 1 1 d . . .
H5A H 0.6559 0.1655 0.0205 0.023 Uiso 1 1 calc R . .
C6 C 0.6845(4) 0.3035(2) 0.0053(7) 0.0213(8) Uani 1 1 d . . .
H6A H 0.6146 0.3149 -0.1382 0.026 Uiso 1 1 calc R . .
C7 C 0.7610(4) 0.3755(2) 0.1182(7) 0.0180(7) Uani 1 1 d . . .
H7A H 0.7428 0.4355 0.0526 0.022 Uiso 1 1 calc R . .

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
Br1 0.03216(19) 0.01307(15) 0.03861(19) 0.00066(15) 0.00128(19) -0.00268(16)
O1 0.0292(19) 0.0234(18) 0.0097(18) 0.000 0.000 -0.0098(15)
N1 0.0180(12) 0.0114(12) 0.0114(10) -0.0029(12) 0.0011(11) -0.0038(10)
C1 0.018(2) 0.012(2) 0.012(2) 0.000 0.000 -0.0009(18)
C2 0.0175(15) 0.0114(13) 0.0100(12) -0.0018(10) 0.0020(13) -0.0024(13)
C3 0.0161(14) 0.0151(14) 0.0144(13) -0.0014(13) 0.0032(13) -0.0006(11)
C4 0.0229(17) 0.0140(15) 0.0193(16) -0.0010(13) 0.0025(13) 0.0000(13)
C5 0.0181(16) 0.0204(16) 0.0188(17) -0.0023(13) 0.0028(13) -0.0055(13)
C6 0.0218(18) 0.0251(17) 0.0171(19) -0.0029(12) -0.0019(12) -0.0036(14)
C7 0.0210(17) 0.0180(16) 0.0152(17) -0.0011(12) 0.0010(13) -0.0021(14)

_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
Br1 C4 1.897(3) . ?
O1 C1 1.243(6) . ?
N1 C1 1.364(3) . ?
N1 C2 1.411(4) . ?
N1 H1A 0.8800 . ?
C1 N1 1.364(3) 2_765 ?
C2 C7 1.386(5) . ?
C2 C3 1.401(4) . ?
C3 C4 1.385(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.395(5) . ?
C5 C6 1.395(5) . ?
C5 H5A 0.9500 . ?
C6 C7 1.388(5) . ?
C6 H6A 0.9500 . ?
C7 H7A 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
C1 N1 C2 123.5(3) . . ?
C1 N1 H1A 118.2 . . ?
C2 N1 H1A 118.2 . . ?
O1 C1 N1 122.2(2) . . ?
O1 C1 N1 122.2(2) . 2_765 ?
N1 C1 N1 115.6(4) . 2_765 ?
C7 C2 C3 119.9(3) . . ?
C7 C2 N1 122.3(3) . . ?
C3 C2 N1 117.8(3) . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3A 120.5 . . ?
C2 C3 H3A 120.5 . . ?
C3 C4 C5 122.3(3) . . ?
C3 C4 Br1 118.5(3) . . ?
C5 C4 Br1 119.2(3) . . ?
C6 C5 C4 117.4(3) . . ?
C6 C5 H5A 121.3 . . ?
C4 C5 H5A 121.3 . . ?
C7 C6 C5 121.4(3) . . ?
C7 C6 H6A 119.3 . . ?
C5 C6 H6A 119.3 . . ?
C2 C7 C6 120.1(3) . . ?
C2 C7 H7A 120.0 . . ?
C6 C7 H7A 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 O1 -8.9(3) . . . . ?
C2 N1 C1 N1 171.1(3) . . . 2_765 ?
C1 N1 C2 C7 -44.4(4) . . . . ?
C1 N1 C2 C3 137.3(3) . . . . ?
C7 C2 C3 C4 0.7(5) . . . . ?
N1 C2 C3 C4 179.0(3) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C2 C3 C4 Br1 178.7(2) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
Br1 C4 C5 C6 -179.2(3) . . . . ?
C4 C5 C6 C7 0.2(5) . . . . ?
C3 C2 C7 C6 -0.9(5) . . . . ?
N1 C2 C7 C6 -179.1(3) . . . . ?
C5 C6 C7 C2 0.4(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        29.08
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.833
_refine_diff_density_rms         0.105

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 2'
_symmetry_int_tables_number      18
_symmetry_space_group_name_Hall  'P 2 2ab'

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-10.00 -14.00 1.00 0.0486
10.00 -15.00 0.00 0.0185
1.00 1.00 -6.00 0.3200
-1.00 -1.00 6.00 0.2956
-9.00 13.00 3.00 0.1366
3.00 -20.00 0.00 0.0123
-11.00 -12.00 0.00 0.0155
11.00 12.00 0.00 0.0124
-9.00 16.00 0.00 0.0185
_audit_creation_date             
;
'Thu Jul 14 13:23:07 2005'
;
_audit_creation_method_reference 
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr 1 2005,17:53:34)
;
_computing_data_collection_reference 
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr 1 2005,17:53:34)
;
_computing_cell_refinment_reference 
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr 1 2005,17:53:34)
;
_computing_data_reduction_reference 
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr 1 2005,17:53:34)
;
_cell_measurement_theta_min      4.1351
_cell_measurement_theta_max      28.9932
_cell_measurement_resolution_max 0.73
_cell_measurement_temperature    110
_exptl_crystal_size_max          0.32000
_exptl_crystal_size_mid          0.09754
_exptl_crystal_size_min          0.01231
_exptl_absorpt_coefficient_mu    6.30072
_exptl_absorpt_correction_T_min  0.23571
_exptl_absorpt_correction_T_max  0.85632
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr 1 2005,17:53:34)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
;
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 15.9890
_diffrn_orient_matrix_UB_11      -0.0112271755
_diffrn_orient_matrix_UB_12      -0.0639829484
_diffrn_orient_matrix_UB_13      -0.0241408655
_diffrn_orient_matrix_UB_21      0.0036623704
_diffrn_orient_matrix_UB_22      -0.0375952840
_diffrn_orient_matrix_UB_23      0.0414844495
_diffrn_orient_matrix_UB_31      -0.1551491134
_diffrn_orient_matrix_UB_32      0.0037196847
_diffrn_orient_matrix_UB_33      0.0026839577
_diffrn_measurement_details      'see scan set'

_diffrn_measurement_method       ' omega scans'

_diffrn_source_power             2
_diffrn_source_voltage           50
_diffrn_source_current           40
_diffrn_measurement_device       Kappa
_diffrn_measurement_device_type  Xcalibur3
_diffrn_ambient_temperature      110
_exptl_crystal_recrystallization_method benzene

#===END

# Attachment 'mClMePU_done.cif'

data_mClMePU
_database_code_depnum_ccdc_archive 'CCDC 695367'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '1-(m-chlorophenyl)-3-(m-tolyl) urea'
_chemical_name_common            '1-(m-chlorophenyl)-3-(m-tolyl) urea'
_chemical_melting_point          235.3
_chemical_formula_moiety         'C14 H13 Cl N2 O'
_chemical_formula_sum            'C14 H13 Cl N2 O'
_chemical_formula_weight         260.71

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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                   9.5777(5)
_cell_length_b                   14.3646(7)
_cell_length_c                   4.5596(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     627.31(5)
_cell_formula_units_Z            2

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272

_exptl_special_details           
;
?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'

_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         ?
_diffrn_standards_interval_count 1
_diffrn_standards_interval_time  50
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9349
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         4.47
_diffrn_reflns_theta_max         28.55
_diffrn_reflns_resolution_max    0.74
_reflns_number_total             1597
_reflns_number_gt                1387
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Oxford Diffraction CrysAlis CCD'
_computing_cell_refinement       'Oxford Diffraction CrysAlis RED'
_computing_data_reduction        'Oxford Diffraction CrysAlis RED'
_computing_structure_solution    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_structure_refinement  'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_molecular_graphics    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_publication_material  'Sheldrick, G.M. (2000). SHELXTL v6.10.'

_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.

Chloro-methyl disorder at C4 resulted in oscillating parameters which prevented
refinement to convergence. Two restraints where used to fix the position
of these atoms and eliminate oscillation.
;

_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)+(0.0595P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(11)
_refine_ls_number_reflns         1597
_refine_ls_number_parameters     97
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1026
_refine_ls_wR_factor_gt          0.0983
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.122
_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
Cl1 Cl 0.6550(3) 0.58164(15) 0.9402(8) 0.0412(5) Uani 0.50 1 d PD A 1
N1 N 0.55787(13) 0.93033(9) 0.9576(3) 0.0218(3) Uani 1 1 d . . .
H1 H 0.551(2) 0.9356(16) 1.136(5) 0.040(6) Uiso 1 1 d . . .
O1 O 0.5000 1.0000 0.5266(3) 0.0260(4) Uani 1 2 d S . .
C1 C 0.5000 1.0000 0.7981(5) 0.0208(5) Uani 1 2 d S . .
C2 C 0.63557(16) 0.85650(10) 0.8323(3) 0.0216(3) Uani 1 1 d . . .
C3 C 0.60927(16) 0.76637(11) 0.9306(4) 0.0245(3) Uani 1 1 d . A .
H3 H 0.5397 0.7553 1.0750 0.029 Uiso 1 1 calc R . .
C4 C 0.68584(18) 0.69281(10) 0.8154(4) 0.0290(4) Uani 1 1 d D . .
C5 C 0.78656(18) 0.70853(12) 0.6062(4) 0.0332(4) Uani 1 1 d . A .
H5 H 0.8381 0.6580 0.5267 0.040 Uiso 1 1 calc R . .
C6 C 0.81241(19) 0.79855(13) 0.5124(4) 0.0340(4) Uani 1 1 d . . .
H6 H 0.8822 0.8094 0.3683 0.041 Uiso 1 1 calc R A .
C7 C 0.73825(16) 0.87289(12) 0.6253(4) 0.0273(4) Uani 1 1 d . A .
H7 H 0.7576 0.9345 0.5616 0.033 Uiso 1 1 calc R . .
C8 C 0.6491(17) 0.5944(5) 0.903(4) 0.069(5) Uani 0.50 1 d PD A 2
H8A H 0.5839 0.5681 0.7592 0.104 Uiso 0.50 1 calc PR A 2
H8B H 0.6055 0.5947 1.0970 0.104 Uiso 0.50 1 calc PR A 2
H8C H 0.7342 0.5565 0.9082 0.104 Uiso 0.50 1 calc PR 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
Cl1 0.0448(8) 0.0179(4) 0.0609(11) -0.0002(6) -0.0079(7) 0.0026(5)
N1 0.0294(7) 0.0197(6) 0.0162(6) -0.0014(5) 0.0022(5) 0.0034(5)
O1 0.0340(9) 0.0255(8) 0.0184(8) 0.000 0.000 0.0064(6)
C1 0.0226(10) 0.0203(10) 0.0196(10) 0.000 0.000 -0.0021(8)
C2 0.0240(7) 0.0209(7) 0.0200(7) -0.0031(6) -0.0036(6) 0.0025(6)
C3 0.0238(7) 0.0224(7) 0.0272(8) -0.0004(7) -0.0039(7) 0.0015(6)
C4 0.0310(8) 0.0204(7) 0.0357(9) -0.0049(7) -0.0099(7) 0.0042(6)
C5 0.0323(9) 0.0343(9) 0.0328(9) -0.0109(7) -0.0069(8) 0.0134(7)
C6 0.0289(8) 0.0450(10) 0.0280(9) -0.0040(8) 0.0011(7) 0.0077(8)
C7 0.0265(8) 0.0284(8) 0.0269(9) -0.0008(7) -0.0005(7) 0.0019(6)
C8 0.084(7) 0.055(7) 0.069(7) 0.000(4) 0.010(5) 0.024(4)

_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
Cl1 C4 1.721(3) . ?
N1 C1 1.3555(17) . ?
N1 C2 1.4159(19) . ?
N1 H1 0.82(2) . ?
O1 C1 1.238(3) . ?
C1 N1 1.3554(17) 2_675 ?
C2 C7 1.383(2) . ?
C2 C3 1.393(2) . ?
C3 C4 1.390(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(2) . ?
C4 C8 1.510(5) . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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
C1 N1 C2 123.47(14) . . ?
C1 N1 H1 115.5(16) . . ?
C2 N1 H1 120.8(16) . . ?
O1 C1 N1 122.43(9) . 2_675 ?
O1 C1 N1 122.43(9) . . ?
N1 C1 N1 115.14(19) 2_675 . ?
C7 C2 C3 120.43(15) . . ?
C7 C2 N1 121.43(14) . . ?
C3 C2 N1 118.10(14) . . ?
C4 C3 C2 119.31(15) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C5 C4 C3 120.51(15) . . ?
C5 C4 C8 120.0(7) . . ?
C3 C4 C8 119.3(7) . . ?
C5 C4 Cl1 120.15(17) . . ?
C3 C4 Cl1 119.34(18) . . ?
C4 C5 C6 119.54(15) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 120.99(17) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C2 119.21(16) . . ?
C6 C7 H7 120.4 . . ?
C2 C7 H7 120.4 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 O1 6.67(15) . . . . ?
C2 N1 C1 N1 -173.33(15) . . . 2_675 ?
C1 N1 C2 C7 46.7(2) . . . . ?
C1 N1 C2 C3 -135.53(14) . . . . ?
C7 C2 C3 C4 -1.0(2) . . . . ?
N1 C2 C3 C4 -178.80(15) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C2 C3 C4 C8 -174.8(7) . . . . ?
C2 C3 C4 Cl1 179.18(17) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C8 C4 C5 C6 175.4(7) . . . . ?
Cl1 C4 C5 C6 -178.61(18) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C5 C6 C7 C2 -0.8(3) . . . . ?
C3 C2 C7 C6 1.4(2) . . . . ?
N1 C2 C7 C6 179.16(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.55
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.045

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 2'
_symmetry_int_tables_number      18
_symmetry_space_group_name_Hall  'P 2 2ab'

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
12.00 10.00 0.00 0.0452
-12.00 -9.00 0.00 0.0248
7.00 -7.00 -5.00 0.1924
11.00 -11.00 0.00 0.0436
-11.00 11.00 0.00 0.0218
9.00 -6.00 5.00 0.1762
_audit_creation_date             
;
'Fri Jun 30 15:37:57 2006'
;
_audit_creation_method_reference 
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.5 (release 22-02-2006 CrysAlis171 .NET)
(compiled Feb 22 2006,13:01:44)
;
_computing_data_collection_reference 
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.29.5 (release 22-02-2006 CrysAlis171 .NET)
(compiled Feb 22 2006,13:01:44)
;
_computing_cell_refinment_reference 
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.5 (release 22-02-2006 CrysAlis171 .NET)
(compiled Feb 22 2006,13:01:44)
;
_computing_data_reduction_reference 
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.5 (release 22-02-2006 CrysAlis171 .NET)
(compiled Feb 22 2006,13:01:44)
;
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      4.2476
_cell_measurement_theta_max      28.4915
_cell_measurement_resolution_max 0.74
_cell_measurement_temperature    110
_exptl_crystal_size_max          0.1923
_exptl_crystal_size_mid          0.0840
_exptl_crystal_size_min          0.0218
_exptl_absorpt_coefficient_mu    0.293
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.5 (release 22-02-2006 CrysAlis171 .NET)
(compiled Feb 22 2006,13:01:44)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 15.9890
_diffrn_orient_matrix_UB_11      -0.0189040031
_diffrn_orient_matrix_UB_12      0.0463916780
_diffrn_orient_matrix_UB_13      0.0380088770
_diffrn_orient_matrix_UB_21      -0.1056461910
_diffrn_orient_matrix_UB_22      0.0380503592
_diffrn_orient_matrix_UB_23      -0.0259155703
_diffrn_orient_matrix_UB_31      -0.1126077590
_diffrn_orient_matrix_UB_32      -0.0434104360
_diffrn_orient_matrix_UB_33      0.0179422285
_diffrn_measurement_details      'see scan set'

loop_
_diffrn_scan_number
_diffrn_scan_type
_diffrn_scan_start
_diffrn_scan_end
_diffrn_scan_width
_diffrn_scan_exptime
_diffrn_scan_omega
_diffrn_scan_theta
_diffrn_scan_kappa
_diffrn_scan_phi
_diffrn_scan_omega1
_diffrn_scan_theta1
_diffrn_scan_frames

1 omega 48.00 95.00 1.00 35.00 - 24.85 58.00 -29.00 0.00 0.00 47
2 omega 48.00 95.00 1.00 35.00 - 24.85 58.00 170.00 0.00 0.00 47
3 omega 5.00 57.00 1.00 35.00 - 24.85 -75.00 240.00 0.00 0.00 52
4 omega 1.00 48.00 1.00 35.00 - 24.85 58.00 170.00 0.00 0.00 47
5 omega -19.00 30.00 1.00 35.00 - -25.62 95.00 89.00 0.00 0.00 49
6 omega -49.00 -2.00 1.00 35.00 - -25.62 58.00 -29.00 0.00 0.00 47
7 omega -40.00 4.00 1.00 35.00 - -25.62 124.00 22.00 0.00 0.00 44
8 omega -19.00 25.00 1.00 35.00 - -25.62 95.00 -90.00 0.00 0.00 44
9 omega -48.00 2.00 1.00 35.00 - -25.62 -45.00 240.00 0.00 0.00 50
10 omega -68.00 -19.00 1.00 35.00 - -25.62 95.00 -159.00 0.00 0.00 49
11 omega -98.00 -48.00 1.00 35.00 - -25.62 -45.00 240.00 0.00 0.00 50
12 omega -68.00 -19.00 1.00 35.00 - -25.62 95.00 89.00 0.00 0.00 49
13 omega -68.00 -30.00 1.00 35.00 - -25.62 95.00 20.00 0.00 0.00 38
14 omega -2.00 45.00 1.00 35.00 - -25.62 58.00 170.00 0.00 0.00 47
15 omega -31.00 -3.00 1.00 35.00 - -25.62 45.00 240.00 0.00 0.00 28
16 omega -49.00 -21.00 1.00 35.00 - -25.62 58.00 170.00 0.00 0.00 28
17 omega -3.00 25.00 1.00 35.00 - -25.62 45.00 240.00 0.00 0.00 28

_diffrn_measurement_method       ' omega scans'

_diffrn_source_power             2
_diffrn_source_voltage           50
_diffrn_source_current           40
_diffrn_measurement_device       Kappa
_diffrn_measurement_device_type  Xcalibur3
_diffrn_ambient_temperature      110
_exptl_crystal_recrystallization_method benzene

#===END


#===END

# Attachment 'mClPU_done.CIF'

data_mClPU
_database_code_depnum_ccdc_archive 'CCDC 695368'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        1,3-bis(m-chlorophenyl)urea
_chemical_name_common            mClPU
_chemical_melting_point          244.7
_chemical_formula_moiety         'C13 H10 Cl2 N2 O'
_chemical_formula_sum            'C13 H10 Cl2 N2 O'
_chemical_formula_weight         281.13

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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                   9.5880(8)
_cell_length_b                   14.3214(11)
_cell_length_c                   4.5653(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     626.88(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4966
_cell_measurement_theta_min      2.557
_cell_measurement_theta_max      28.320

_exptl_crystal_description       needles
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    0.505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8430
_exptl_absorpt_correction_T_max  0.9512
_exptl_absorpt_process_details   'SADABS, G. Sheldrick (1999)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SMART platform CCD, Siemens'
_diffrn_measurement_method       'omega scans'
_diffrn_reflns_number            5490
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         27.98
_reflns_number_total             1483
_reflns_number_gt                1425
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART, Siemens'
_computing_cell_refinement       'SAINT, Siemens'
_computing_data_reduction        'SAINT, Siemens'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-SEED, L.Barbour(1999); http://x-seed.net/'

_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.
;

_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)+(0.0398P)²+0.1283P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.007(7)
_refine_ls_number_reflns         1483
_refine_ls_number_parameters     87
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0263
_refine_ls_wR_factor_ref         0.0715
_refine_ls_wR_factor_gt          0.0707
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_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_symetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.15472(5) 0.41943(3) 0.42691(12) 0.04928(15) Uani 1 1 d . . .
N1 N 0.05747(12) 0.06999(8) 0.4604(2) 0.0221(2) Uani 1 1 d . . .
O1 O 0.0000 0.0000 0.0298(3) 0.0271(3) Uani 1 2 d S . .
C3 C 0.11132(13) 0.23404(9) 0.4291(3) 0.0245(3) Uani 1 1 d . . .
H3 H 0.0418 0.2464 0.5721 0.029 Uiso 1 1 calc R . .
C2 C 0.13663(13) 0.14327(8) 0.3352(3) 0.0210(2) Uani 1 1 d . . .
C5 C 0.29065(15) 0.29061(11) 0.1015(3) 0.0337(3) Uani 1 1 d . . .
H5 H 0.3423 0.3410 0.0209 0.040 Uiso 1 1 calc R . .
C1 C 0.0000 0.0000 0.3013(4) 0.0197(3) Uani 1 2 d S . .
C7 C 0.23972(14) 0.12572(10) 0.1277(3) 0.0268(3) Uani 1 1 d . . .
H7 H 0.2581 0.0636 0.0658 0.032 Uiso 1 1 calc R . .
C4 C 0.18934(15) 0.30625(9) 0.3104(3) 0.0298(3) Uani 1 1 d . . .
C6 C 0.31539(15) 0.19964(12) 0.0119(3) 0.0338(3) Uani 1 1 d . . .
H6 H 0.3852 0.1877 -0.1309 0.041 Uiso 1 1 calc R . .
H1 H 0.0478(16) 0.0671(12) 0.636(4) 0.025(4) Uiso 1 1 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
Cl1 0.0573(3) 0.01981(18) 0.0708(3) 0.00019(19) -0.0043(2) -0.00693(16)
N1 0.0312(5) 0.0211(5) 0.0138(5) -0.0001(4) 0.0014(4) -0.0050(4)
O1 0.0374(7) 0.0295(7) 0.0144(6) 0.000 0.000 -0.0106(6)
C3 0.0257(6) 0.0228(6) 0.0251(6) 0.0003(5) -0.0039(5) -0.0020(4)
C2 0.0243(6) 0.0213(6) 0.0175(5) 0.0028(4) -0.0030(5) -0.0037(4)
C5 0.0320(7) 0.0364(8) 0.0326(7) 0.0112(6) -0.0065(6) -0.0151(6)
C1 0.0218(8) 0.0204(8) 0.0169(7) 0.000 0.000 -0.0004(6)
C7 0.0266(6) 0.0304(7) 0.0235(6) -0.0005(5) 0.0007(5) -0.0033(5)
C4 0.0318(7) 0.0226(6) 0.0350(7) 0.0038(6) -0.0106(6) -0.0048(5)
C6 0.0274(6) 0.0458(9) 0.0280(7) 0.0038(6) 0.0033(5) -0.0092(6)

_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
Cl1 C4 1.7379(15) . ?
N1 C1 1.3552(14) . ?
N1 C2 1.4157(15) . ?
N1 H1 0.807(19) . ?
O1 C1 1.239(2) . ?
C3 C4 1.3867(18) . ?
C3 C2 1.3901(18) . ?
C3 H3 0.9500 . ?
C2 C7 1.3918(18) . ?
C5 C4 1.379(2) . ?
C5 C6 1.386(2) . ?
C5 H5 0.9500 . ?
C1 N1 1.3552(14) 2 ?
C7 C6 1.388(2) . ?
C7 H7 0.9500 . ?
C6 H6 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
C1 N1 C2 123.34(11) . . ?
C1 N1 H1 116.5(12) . . ?
C2 N1 H1 120.0(12) . . ?
C4 C3 C2 118.87(13) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C2 C7 120.18(12) . . ?
C3 C2 N1 118.36(11) . . ?
C7 C2 N1 121.45(11) . . ?
C4 C5 C6 118.50(13) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
O1 C1 N1 122.43(8) . . ?
O1 C1 N1 122.43(8) . 2 ?
N1 C1 N1 115.14(15) . 2 ?
C6 C7 C2 119.51(13) . . ?
C6 C7 H7 120.2 . . ?
C2 C7 H7 120.2 . . ?
C5 C4 C3 121.93(13) . . ?
C5 C4 Cl1 119.84(11) . . ?
C3 C4 Cl1 118.22(12) . . ?
C5 C6 C7 121.01(14) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.98
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.040

_exptl_crystal_recrystallization_method ethanol
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_h-m   'P 21 21 2'
_symmetry_int_tables_number      18
_symmetry_space_group_name_Hall  'P 2 2ab'

#===END

# Attachment 'mIPU_done.cif'

data_mIPU
_database_code_depnum_ccdc_archive 'CCDC 695369'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '1,3-bis(m-iodophenyl) urea'
_chemical_name_common            mIPU
_chemical_melting_point          282.8
_chemical_formula_moiety         'C13 H10 I2 N2 O'
_chemical_formula_sum            'C13 H10 I2 N2 O'
_chemical_formula_weight         464.03

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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                   9.6345(11)
_cell_length_b                   15.3998(14)
_cell_length_c                   4.5673(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     677.65(15)
_cell_formula_units_Z            2

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.274
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432

_exptl_special_details           
;
?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'

_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         ?
_diffrn_standards_interval_count 1
_diffrn_standards_interval_time  50
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6763
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         4.43
_diffrn_reflns_theta_max         28.06
_diffrn_reflns_resolution_max    0.76
_reflns_number_total             1641
_reflns_number_gt                1605
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Oxford Diffraction CrysAlis CCD'
_computing_cell_refinement       'Oxford Diffraction CrysAlis RED'
_computing_data_reduction        'Oxford Diffraction CrysAlis RED'
_computing_structure_solution    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_structure_refinement  'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_molecular_graphics    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_publication_material  'Sheldrick, G.M. (2000). SHELXTL v6.10.'

_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.
;

_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)+(0.0150P)²+0.8840P] 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   0.04(3)
_refine_ls_number_reflns         1641
_refine_ls_number_parameters     83
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0210
_refine_ls_R_factor_gt           0.0201
_refine_ls_wR_factor_ref         0.0417
_refine_ls_wR_factor_gt          0.0413
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_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
I1 I 0.85282(2) 0.086243(12) 0.03574(5) 0.02056(7) Uani 1 1 d . . .
O1 O 1.0000 0.5000 0.5031(8) 0.0205(7) Uani 1 2 d S . .
N1 N 0.9452(3) 0.43330(14) 0.0689(6) 0.0120(5) Uani 1 1 d . . .
H1N H 0.9594 0.4334 -0.1214 0.014 Uiso 1 1 calc R . .
C1 C 1.0000 0.5000 0.2315(10) 0.0121(8) Uani 1 2 d S . .
C2 C 0.8670(3) 0.36438(19) 0.1911(6) 0.0120(6) Uani 1 1 d . . .
C3 C 0.8912(3) 0.28076(19) 0.0844(7) 0.0129(6) Uani 1 1 d . . .
H3A H 0.9608 0.2709 -0.0593 0.016 Uiso 1 1 calc R . .
C4 C 0.8122(3) 0.2122(2) 0.1912(7) 0.0141(6) Uani 1 1 d . . .
C5 C 0.7092(3) 0.2251(2) 0.4002(7) 0.0161(6) Uani 1 1 d . . .
H5A H 0.6554 0.1779 0.4712 0.019 Uiso 1 1 calc R . .
C6 C 0.6870(3) 0.3091(2) 0.5024(8) 0.0163(6) Uani 1 1 d . . .
H6A H 0.6174 0.3190 0.6459 0.020 Uiso 1 1 calc R . .
C7 C 0.7645(3) 0.3787(2) 0.3993(7) 0.0143(6) Uani 1 1 d . . .
H7A H 0.7475 0.4356 0.4706 0.017 Uiso 1 1 calc R . .

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
I1 0.02301(10) 0.00986(8) 0.02883(11) -0.00176(8) -0.00047(9) -0.00195(9)
O1 0.0296(17) 0.0227(15) 0.0093(17) 0.000 0.000 -0.0111(13)
N1 0.0126(11) 0.0102(11) 0.0131(11) 0.0013(10) 0.0012(11) -0.0019(9)
C1 0.015(2) 0.0093(19) 0.012(2) 0.000 0.000 0.0007(16)
C2 0.0122(15) 0.0138(13) 0.0101(13) 0.0014(10) -0.0032(13) -0.0009(12)
C3 0.0131(14) 0.0150(13) 0.0107(14) 0.0010(11) -0.0002(11) 0.0001(10)
C4 0.0163(16) 0.0106(14) 0.0155(15) 0.0020(12) -0.0035(12) 0.0000(11)
C5 0.0133(14) 0.0183(14) 0.0168(16) 0.0031(12) -0.0004(12) -0.0035(12)
C6 0.0148(14) 0.0223(14) 0.0117(16) -0.0004(13) 0.0004(12) -0.0010(11)
C7 0.0161(15) 0.0137(13) 0.0131(15) -0.0015(11) -0.0013(12) 0.0023(12)

_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
I1 C4 2.102(3) . ?
O1 C1 1.240(6) . ?
N1 C1 1.373(3) . ?
N1 C2 1.416(4) . ?
N1 H1N 0.8800 . ?
C1 N1 1.373(3) 2_765 ?
C2 C7 1.389(4) . ?
C2 C3 1.397(4) . ?
C3 C4 1.390(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.392(4) . ?
C5 C6 1.391(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.388(4) . ?
C6 H6A 0.9500 . ?
C7 H7A 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
C1 N1 C2 123.5(3) . . ?
C1 N1 H1N 118.2 . . ?
C2 N1 H1N 118.2 . . ?
O1 C1 N1 122.74(19) . 2_765 ?
O1 C1 N1 122.74(19) . . ?
N1 C1 N1 114.5(4) 2_765 . ?
C7 C2 C3 120.3(3) . . ?
C7 C2 N1 122.0(3) . . ?
C3 C2 N1 117.7(3) . . ?
C4 C3 C2 119.1(3) . . ?
C4 C3 H3A 120.4 . . ?
C2 C3 H3A 120.4 . . ?
C3 C4 C5 121.5(3) . . ?
C3 C4 I1 118.7(2) . . ?
C5 C4 I1 119.8(2) . . ?
C6 C5 C4 118.2(3) . . ?
C6 C5 H5A 120.9 . . ?
C4 C5 H5A 120.9 . . ?
C7 C6 C5 121.4(3) . . ?
C7 C6 H6A 119.3 . . ?
C5 C6 H6A 119.3 . . ?
C6 C7 C2 119.5(3) . . ?
C6 C7 H7A 120.3 . . ?
C2 C7 H7A 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 O1 9.0(3) . . . . ?
C2 N1 C1 N1 -171.0(3) . . . 2_765 ?
C1 N1 C2 C7 44.1(4) . . . . ?
C1 N1 C2 C3 -139.0(2) . . . . ?
C7 C2 C3 C4 -0.5(4) . . . . ?
N1 C2 C3 C4 -177.4(3) . . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C2 C3 C4 I1 -178.6(2) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
I1 C4 C5 C6 178.7(2) . . . . ?
C4 C5 C6 C7 0.3(5) . . . . ?
C5 C6 C7 C2 -0.4(5) . . . . ?
C3 C2 C7 C6 0.5(5) . . . . ?
N1 C2 C7 C6 177.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.06
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.895
_refine_diff_density_rms         0.099

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 2'
_symmetry_int_tables_number      18
_symmetry_space_group_name_Hall  'P 2 2ab'

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 -1.00 6.00 0.2585
13.00 4.00 0.00 0.0185
13.00 -7.00 0.00 0.0169
-13.00 -4.00 0.00 0.0154
0.00 -22.00 0.00 0.0277
0.00 22.00 0.00 0.0108
2.00 4.00 -6.00 0.2535
-13.00 7.00 0.00 0.0092
_audit_creation_date             
;
'Wed Jul 13 15:02:00 2005'
;
_audit_creation_method_reference 
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr 1 2005,17:53:34)
;
_computing_data_collection_reference 
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr 1 2005,17:53:34)
;
_computing_cell_refinment_reference 
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr 1 2005,17:53:34)
;
_computing_data_reduction_reference 
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr 1 2005,17:53:34)
;
_cell_measurement_theta_min      3.9616
_cell_measurement_theta_max      27.9945
_cell_measurement_resolution_max 0.76
_cell_measurement_temperature    110
_exptl_crystal_size_max          0.25850
_exptl_crystal_size_mid          0.07631
_exptl_crystal_size_min          0.00923
_exptl_absorpt_coefficient_mu    4.63032
_exptl_absorpt_correction_T_min  0.49796
_exptl_absorpt_correction_T_max  0.89283
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr 1 2005,17:53:34)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
;
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 15.9890
_diffrn_orient_matrix_UB_11      0.0063037809
_diffrn_orient_matrix_UB_12      -0.0667429280
_diffrn_orient_matrix_UB_13      0.0193207806
_diffrn_orient_matrix_UB_21      -0.0063538643
_diffrn_orient_matrix_UB_22      -0.0310473965
_diffrn_orient_matrix_UB_23      -0.0417361795
_diffrn_orient_matrix_UB_31      0.1550416368
_diffrn_orient_matrix_UB_32      0.0012334506
_diffrn_orient_matrix_UB_33      -0.0024948420
_diffrn_measurement_details      'see scan set'

_diffrn_measurement_method       ' omega scans'

_diffrn_source_power             2
_diffrn_source_voltage           50
_diffrn_source_current           40
_diffrn_measurement_device       Kappa
_diffrn_measurement_device_type  Xcalibur3
_diffrn_ambient_temperature      110
_exptl_crystal_recrystallization_method benzene

#===END

# Attachment 'mMePU_done.cif'

data_mMePU
_database_code_depnum_ccdc_archive 'CCDC 695370'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '1,3-bis(tolyl) urea'
_chemical_name_common            mMePU
_chemical_melting_point          222.6
_chemical_formula_moiety         'C15 H16 N2 O'
_chemical_formula_sum            'C15 H16 N2 O'
_chemical_formula_weight         240.30

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'

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                   9.5950(16)
_cell_length_b                   14.521(2)
_cell_length_c                   4.5902(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     639.6(2)
_cell_formula_units_Z            2

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256

_exptl_special_details           
;
?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'

_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_number         ?
_diffrn_standards_interval_count 1
_diffrn_standards_interval_time  50
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            717
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         4.25
_diffrn_reflns_theta_max         25.31
_diffrn_reflns_resolution_max    0.83
_reflns_number_total             717
_reflns_number_gt                705
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Oxford Diffraction CrysAlis CCD'
_computing_cell_refinement       'Oxford Diffraction CrysAlis RED'
_computing_data_reduction        'Oxford Diffraction CrysAlis RED'
_computing_structure_solution    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_structure_refinement  'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_molecular_graphics    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_publication_material  'Sheldrick, G.M. (2000). SHELXTL v6.10.'

_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.
;

_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)+(0.0388P)²+0.3931P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -7(5)
_refine_ls_number_reflns         717
_refine_ls_number_parameters     88
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.1140
_refine_ls_wR_factor_gt          0.1132
_refine_ls_goodness_of_fit_ref   1.213
_refine_ls_restrained_S_all      1.213
_refine_ls_shift/su_max          0.000
_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
N1 N 0.5592(3) 0.06846(17) 0.4535(7) 0.0200(6) Uani 1 1 d . . .
H1N H 0.546(4) 0.065(2) 0.643(9) 0.032(10) Uiso 1 1 d . . .
O1 O 0.5000 0.0000 0.0233(7) 0.0252(8) Uani 1 2 d S . .
C1 C 0.5000 0.0000 0.2940(10) 0.0177(10) Uani 1 2 d S . .
C2 C 0.6352(3) 0.1432(2) 0.3319(7) 0.0193(7) Uani 1 1 d . . .
C3 C 0.6079(3) 0.2314(2) 0.4325(8) 0.0241(8) Uani 1 1 d . . .
H3A H 0.5385 0.2406 0.5771 0.029 Uiso 1 1 calc R . .
C4 C 0.6815(3) 0.3066(2) 0.3230(8) 0.0279(8) Uani 1 1 d . . .
C5 C 0.7834(4) 0.2914(2) 0.1138(8) 0.0325(9) Uani 1 1 d . . .
H5A H 0.8350 0.3419 0.0385 0.039 Uiso 1 1 calc R . .
C6 C 0.8105(4) 0.2033(2) 0.0139(8) 0.0328(9) Uani 1 1 d . . .
H6A H 0.8799 0.1939 -0.1306 0.039 Uiso 1 1 calc R . .
C7 C 0.7372(3) 0.1288(2) 0.1228(7) 0.0256(8) Uani 1 1 d . . .
H7A H 0.7567 0.0683 0.0550 0.031 Uiso 1 1 calc R . .
C8 C 0.6493(4) 0.4025(2) 0.4335(11) 0.0447(12) Uani 1 1 d . . .
H8A H 0.7294 0.4428 0.3979 0.067 Uiso 1 1 calc R . .
H8B H 0.6301 0.4000 0.6431 0.067 Uiso 1 1 calc R . .
H8C H 0.5675 0.4267 0.3312 0.067 Uiso 1 1 calc R . .

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
N1 0.0288(15) 0.0174(13) 0.0137(14) -0.0021(11) 0.0008(13) -0.0061(11)
O1 0.0318(18) 0.0288(17) 0.0151(17) 0.000 0.000 -0.0050(14)
C1 0.020(2) 0.014(2) 0.019(2) 0.000 0.000 0.0035(18)
C2 0.0172(15) 0.0213(15) 0.0192(16) 0.0021(14) -0.0033(15) -0.0028(13)
C3 0.0211(17) 0.0237(16) 0.0275(19) 0.0023(14) -0.0038(16) -0.0018(13)
C4 0.0258(17) 0.0227(17) 0.035(2) 0.0089(17) -0.0133(17) -0.0046(14)
C5 0.0284(19) 0.036(2) 0.033(2) 0.0128(17) -0.0096(17) -0.0157(16)
C6 0.0250(17) 0.048(2) 0.0250(19) 0.0056(19) 0.0015(16) -0.0105(16)
C7 0.0249(18) 0.0288(18) 0.0233(19) 0.0003(14) -0.0010(15) -0.0019(14)
C8 0.048(2) 0.0215(17) 0.065(3) 0.0010(19) -0.010(3) -0.0056(16)

_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
N1 C1 1.359(3) . ?
N1 C2 1.422(4) . ?
N1 H1N 0.88(4) . ?
O1 C1 1.243(6) . ?
C1 N1 1.359(3) 2_655 ?
C2 C3 1.386(4) . ?
C2 C7 1.387(4) . ?
C3 C4 1.394(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.388(5) . ?
C4 C8 1.514(5) . ?
C5 C6 1.383(5) . ?
C5 H5A 0.9500 . ?
C6 C7 1.384(5) . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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
C1 N1 C2 124.2(3) . . ?
C1 N1 H1N 115(2) . . ?
C2 N1 H1N 120(2) . . ?
O1 C1 N1 122.58(19) . 2_655 ?
O1 C1 N1 122.58(19) . . ?
N1 C1 N1 114.8(4) 2_655 . ?
C3 C2 C7 120.2(3) . . ?
C3 C2 N1 118.5(3) . . ?
C7 C2 N1 121.2(3) . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 C8 121.5(3) . . ?
C3 C4 C8 119.7(3) . . ?
C6 C5 C4 120.6(3) . . ?
C6 C5 H5A 119.7 . . ?
C4 C5 H5A 119.7 . . ?
C5 C6 C7 120.5(3) . . ?
C5 C6 H6A 119.7 . . ?
C7 C6 H6A 119.7 . . ?
C6 C7 C2 119.4(3) . . ?
C6 C7 H7A 120.3 . . ?
C2 C7 H7A 120.3 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 O1 -4.6(3) . . . . ?
C2 N1 C1 N1 175.4(3) . . . 2_655 ?
C1 N1 C2 C3 134.3(3) . . . . ?
C1 N1 C2 C7 -47.4(4) . . . . ?
C7 C2 C3 C4 0.6(5) . . . . ?
N1 C2 C3 C4 178.9(3) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
C2 C3 C4 C8 179.4(3) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
C8 C4 C5 C6 -179.5(3) . . . . ?
C4 C5 C6 C7 -0.6(5) . . . . ?
C5 C6 C7 C2 0.6(5) . . . . ?
C3 C2 C7 C6 -0.6(5) . . . . ?
N1 C2 C7 C6 -178.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.31
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.043

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 2'
_symmetry_int_tables_number      18
_symmetry_space_group_name_Hall  'P 2 2ab'

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4.00 20.00 0.00 0.0233
4.00 -20.00 0.00 0.0139
12.00 10.00 0.00 0.0186
-13.00 -2.00 0.00 0.0083
4.00 3.00 6.00 0.3101
-5.00 -3.00 -6.00 0.3099
_audit_creation_date             
;
'Thu Nov 03 12:20:53 2005'
;
_audit_creation_method_reference 
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr 1 2005,17:53:34)
;
_computing_data_collection_reference 
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr 1 2005,17:53:34)
;
_computing_cell_refinment_reference 
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr 1 2005,17:53:34)
;
_computing_data_reduction_reference 
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr 1 2005,17:53:34)
;
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      26.80
_cell_measurement_resolution_max 0.79
_cell_measurement_reflns_used    1851
_cell_measurement_temperature    110
_exptl_crystal_size_max          0.31008
_exptl_crystal_size_mid          0.11401
_exptl_crystal_size_min          0.00829
_exptl_absorpt_coefficient_mu    0.07971
_exptl_absorpt_correction_T_min  0.97524
_exptl_absorpt_correction_T_max  0.99799
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr 1 2005,17:53:34)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
;
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 15.9890
_diffrn_orient_matrix_UB_11      -0.0666423348
_diffrn_orient_matrix_UB_12      0.0576674779
_diffrn_orient_matrix_UB_13      0.0221322736
_diffrn_orient_matrix_UB_21      0.0078096259
_diffrn_orient_matrix_UB_22      0.0386036239
_diffrn_orient_matrix_UB_23      -0.0415773333
_diffrn_orient_matrix_UB_31      -0.1391980509
_diffrn_orient_matrix_UB_32      -0.0254749263
_diffrn_orient_matrix_UB_33      -0.0129443282
_diffrn_measurement_details      'see scan set'

_diffrn_measurement_method       ' omega scans'

_diffrn_source_power             2
_diffrn_source_voltage           50
_diffrn_source_current           40
_diffrn_measurement_device       Kappa
_diffrn_measurement_device_type  Xcalibur3
_diffrn_ambient_temperature      110
_exptl_crystal_recrystallization_method '1:1 (v/v) ethanol:acetonitrile'

#===END


# Attachment 'mBrMePU_done.CIF'

data_mBrMePU
_database_code_depnum_ccdc_archive 'CCDC 700260'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        '1-(m-bromophenyl)-3-(m-tolyl) urea'
_chemical_name_common            mBrMePU
_chemical_melting_point          247.5
_chemical_formula_moiety         'C14 H13 Br N2 O'
_chemical_formula_sum            'C14 H13 Br N2 O'
_chemical_formula_weight         305.17

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_
_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                   9.5770(16)
_cell_length_b                   14.612(6)
_cell_length_c                   4.5572(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     637.7(3)
_cell_formula_units_Z            2

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             308

_exptl_special_details           
;
?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_standards_number         ?
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5296
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_sigmaI/netI    0.0430
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         4.26
_diffrn_reflns_theta_max         27.60
_reflns_number_total             1476
_reflns_number_gt                1343
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Oxford Diffraction CrysAlis CCD'
_computing_cell_refinement       'Oxford Diffraction CrysAlis RED'
_computing_data_reduction        'Oxford Diffraction CrysAlis RED'
_computing_structure_solution    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_structure_refinement  'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_molecular_graphics    'Sheldrick, G.M. (2000). SHELXTL v6.10.'
_computing_publication_material  'Sheldrick, G.M. (2000). SHELXTL v6.10.'

_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.

Bromo-methyl disorder at C4 resulted in oscillating parameters which prevented
refinement to convergence. Two restraints where used to fix the position
of these atoms and eliminate oscillation.
;

_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)+(0.0000P)²+2.1196P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(3)
_refine_ls_number_reflns         1476
_refine_ls_number_parameters     79
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1222
_refine_ls_wR_factor_gt          0.1205
_refine_ls_goodness_of_fit_ref   1.217
_refine_ls_restrained_S_all      1.221
_refine_ls_shift/su_max          0.000
_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_symetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4423(4) 0.0688(2) 0.4477(9) 0.0180(7) Uani 1 1 d . . .
O1 O 0.5000 0.0000 0.0202(10) 0.0216(10) Uani 1 2 d S . .
C2 C 0.3654(5) 0.1406(3) 0.3279(9) 0.0162(9) Uani 1 1 d . . .
C3 C 0.3910(5) 0.2296(3) 0.4268(12) 0.0202(9) Uani 1 1 d . A .
H3 H 0.4605 0.2406 0.5714 0.024 Uiso 1 1 calc R . .
C1 C 0.5000 0.0000 0.2918(15) 0.0179(13) Uani 1 2 d S . .
C4 C 0.3138(5) 0.3024(3) 0.3117(11) 0.0253(11) Uani 1 1 d D . .
C5 C 0.2115(5) 0.2884(3) 0.1035(12) 0.0272(11) Uani 1 1 d . A .
H5 H 0.1594 0.3383 0.0269 0.033 Uiso 1 1 calc R . .
C7 C 0.2620(5) 0.1255(3) 0.1195(10) 0.0226(10) Uani 1 1 d . A .
H7 H 0.2431 0.0651 0.0535 0.027 Uiso 1 1 calc R . .
C6 C 0.1862(5) 0.1987(3) 0.0076(11) 0.0276(11) Uani 1 1 d . . .
H6 H 0.1162 0.1879 -0.1360 0.033 Uiso 1 1 calc R A .
Br1 Br 0.3510(6) 0.4201(1) 0.4454(5) 0.0303(9) Uani 0.50 1 d PD A 1
C8 C 0.3576(3) 0.3978(1) 0.4011(2) 0.202(6) Uani 0.50 1 d PD A 2
H8A H 0.3848 0.4326 0.2264 0.304 Uiso 0.50 1 calc PR A 2
H8B H 0.4370 0.3941 0.5363 0.304 Uiso 0.50 1 calc PR A 2
H8C H 0.2794 0.4286 0.4986 0.304 Uiso 0.50 1 calc PR A 2
H1 H 0.471(6) 0.062(4) 0.651(16) 0.05(2) Uiso 1 1 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
N1 0.0277(19) 0.0128(16) 0.0135(16) -0.0048(16) -0.0013(17) 0.0037(14)
O1 0.035(3) 0.022(2) 0.008(3) 0.000 0.000 0.0074(19)
C2 0.020(2) 0.0167(18) 0.0113(19) 0.0006(15) 0.0023(18) 0.0013(18)
C3 0.024(2) 0.0173(19) 0.019(2) 0.0010(18) 0.002(2) 0.0019(16)
C1 0.022(3) 0.014(3) 0.018(4) 0.000 0.000 -0.002(2)
C4 0.028(3) 0.022(2) 0.026(3) 0.008(2) 0.009(2) 0.0018(19)
C5 0.027(2) 0.027(2) 0.027(3) 0.012(2) 0.006(2) 0.0117(19)
C7 0.030(2) 0.020(2) 0.018(2) 0.0012(17) 0.001(2) 0.0016(18)
C6 0.027(2) 0.033(2) 0.022(3) 0.0040(19) -0.003(2) 0.0065(19)
Br1 0.036 0.015 0.040 0.001 0.005 0.004
C8 0.299 0.090 0.219 -0.045 -0.180 -0.010

_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
N1 C1 1.349(5) . ?
N1 C2 1.393(5) . ?
N1 H1 0.97(7) . ?
O1 C1 1.238(8) . ?
C2 C7 1.389(6) . ?
C2 C3 1.399(5) . ?
C3 C4 1.397(6) . ?
C3 H3 0.9500 . ?
C1 N1 1.349(5) 2_655 ?
C4 C5 1.380(7) . ?
C4 C8 1.512(4) . ?
C4 Br1 1.859(4) . ?
C5 C6 1.402(7) . ?
C5 H5 0.9500 . ?
C7 C6 1.390(6) . ?
C7 H7 0.9500 . ?
C6 H6 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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
C1 N1 C2 124.8(4) . . ?
C1 N1 H1 108(3) . . ?
C2 N1 H1 127(4) . . ?
C7 C2 N1 121.7(4) . . ?
C7 C2 C3 119.5(4) . . ?
N1 C2 C3 118.8(4) . . ?
C4 C3 C2 119.6(4) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
O1 C1 N1 121.8(3) . . ?
O1 C1 N1 121.8(3) . 2_655 ?
N1 C1 N1 116.5(6) . 2_655 ?
C5 C4 C3 121.4(4) . . ?
C5 C4 C8 121.3(4) . . ?
C3 C4 C8 117.0(4) . . ?
C5 C4 Br1 119.9(3) . . ?
C3 C4 Br1 118.7(4) . . ?
C4 C5 C6 118.4(4) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C2 C7 C6 120.1(4) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C6 C5 121.0(5) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.60
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.087

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 2'
_symmetry_int_tables_number      18
_symmetry_space_group_name_Hall  'P 2 2ab'

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-11.00 11.00 0.00 0.0281
-10.00 -12.00 0.00 0.0127
13.00 -10.00 0.00 0.0279
2.00 3.00 6.00 0.2403
19.00 5.00 0.00 0.0329
7.00 13.00 0.00 0.0269
2.00 1.00 -6.00 0.2424
-20.00 3.00 0.00 0.0326
_audit_creation_date             
;
'Wed Nov 01 11:40:40 2006'
;
_audit_creation_method_reference 
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET)
(compiled Jun 12 2006,17:01:16)
;
_computing_data_collection_reference 
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET)
(compiled Jun 12 2006,17:01:16)
;
_computing_cell_refinment_reference 
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET)
(compiled Jun 12 2006,17:01:16)
;
_computing_data_reduction_reference 
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET)
(compiled Jun 12 2006,17:01:16)
;
_cell_measurement_temperature    110
_cell_measurement_reflns_used    3368
_cell_measurement_theta_min      4.1699
_cell_measurement_theta_max      27.4991
_cell_measurement_resolution_max 0.77
_exptl_crystal_size_max          0.2424
_exptl_crystal_size_mid          0.0805
_exptl_crystal_size_min          0.0127
_exptl_absorpt_coefficient_mu    3.212
_exptl_absorpt_correction_T_min  0.475
_exptl_absorpt_correction_T_max  0.888
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.30.5 (release 12-06-2006 CrysAlis171 .NET)
(compiled Jun 12 2006,17:01:16)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 15.9890
_diffrn_orient_matrix_UB_11      -0.0408943476
_diffrn_orient_matrix_UB_12      -0.0697893338
_diffrn_orient_matrix_UB_13      0.0097873498
_diffrn_orient_matrix_UB_21      -0.0024384520
_diffrn_orient_matrix_UB_22      0.0158965117
_diffrn_orient_matrix_UB_23      0.0473556473
_diffrn_orient_matrix_UB_31      -0.1499387900
_diffrn_orient_matrix_UB_32      0.0187449249
_diffrn_orient_matrix_UB_33      -0.0034363117
_diffrn_measurement_details      'see scan set'

loop_
_diffrn_scan_number
_diffrn_scan_type
_diffrn_scan_start
_diffrn_scan_end
_diffrn_scan_width
_diffrn_scan_exptime
_diffrn_scan_omega
_diffrn_scan_theta
_diffrn_scan_kappa
_diffrn_scan_phi
_diffrn_scan_omega1
_diffrn_scan_theta1
_diffrn_scan_frames

1 omega -7.00 45.00 1.00 60.00 - 24.85 75.00 240.00 0.00 0.00 52
2 omega 28.00 74.00 1.00 60.00 - 24.85 -107.00 117.00 0.00 0.00 46
3 omega 45.00 96.00 1.00 60.00 - 24.85 75.00 240.00 0.00 0.00 51
4 omega -7.00 28.00 1.00 60.00 - 24.85 -107.00 143.00 0.00 0.00 35
5 omega -49.00 -21.00 1.00 60.00 - 24.85 147.00 102.00 0.00 0.00 28
6 omega -41.00 3.00 1.00 60.00 - -25.62 125.00 140.00 0.00 0.00 44
7 phi 0.00 180.00 1.00 60.00 0.00 -30.00 45.00 - 0.00 0.00 180
8 omega -68.00 -29.00 1.00 60.00 - -32.00 31.00 0.00 0.00 0.00 39

_diffrn_measurement_method       'omega phi scans'

_diffrn_source_power             2
_diffrn_source_voltage           50
_diffrn_source_current           40
_diffrn_measurement_device       Kappa
_diffrn_measurement_device_type  Xcalibur3
_diffrn_ambient_temperature      110
_exptl_crystal_recrystallization_method benzene

