Electronic Supplementary Material for CrystEngComm
This journal is (c) The Royal Society of Chemistry 2006

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Thomas Gelbrich'
_publ_contact_author_address     
;
School of Chemistry
University of Southampton
Highfield
Southampton
SO171BJ
UNITED KINGDOM
;

_publ_contact_author_email       GELBRICH@SOTON.AC.UK

_publ_section_title              
;
Systematic investigation of the relationships between
25 crystal structures containing the carbamazepine molecule or a close
analogue - a case study of the XPac method
;
loop_
_publ_author_name
'Thomas Gelbrich'
'M. Hursthouse'
# Attachment 'neu.cif'

data_s92
_database_code_depnum_ccdc_archive 'CCDC 295483'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H16 N2 O3'
_chemical_formula_weight         272.30

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.1051(6)
_cell_length_b                   28.8085(18)
_cell_length_c                   4.8380(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.868(10)
_cell_angle_gamma                90.00
_cell_volume                     1367.35(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9816
_exptl_absorpt_correction_T_max  0.9953
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'

_exptl_special_details           
;
?
;

_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  graphite
_diffrn_measurement_device_type  'Bruker-Nonius 95mm CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_detector_area_resol_mean 9.091
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14361
_diffrn_reflns_av_R_equivalents  0.1094
_diffrn_reflns_av_sigmaI/netI    0.0804
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         25.24
_reflns_number_total             2441
_reflns_number_gt                1487
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0057P)^2^+0.1000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0152(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2441
_refine_ls_number_parameters     203
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.1038
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.0856
_refine_ls_wR_factor_gt          0.0770
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_restrained_S_all      1.168
_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 -0.0028(6) 0.61063(6) 0.2298(4) 0.0226(5) Uani 1 1 d . . .
N2 N -0.1157(4) 0.54675(15) 0.3411(12) 0.0227(7) Uani 1 1 d DU . .
H1N H -0.1970(16) 0.5582(9) 0.267(6) 0.028(9) Uiso 1 1 d D . .
H2N H -0.109(3) 0.5193(6) 0.423(7) 0.057(12) Uiso 1 1 d D . .
O1 O 0.1154(4) 0.54729(13) 0.4501(10) 0.0337(8) Uani 1 1 d D . .
C1 C 0.1208(4) 0.63465(17) 0.2250(11) 0.0209(14) Uani 1 1 d D . .
C2 C 0.1551(4) 0.67493(17) 0.3882(12) 0.0221(15) Uani 1 1 d D . .
C3 C 0.0665(5) 0.69557(17) 0.5552(12) 0.0219(14) Uani 1 1 d D . .
H3 H 0.1093 0.7096 0.7317 0.026 Uiso 1 1 calc R . .
C4 C 0.2788(4) 0.69676(16) 0.3826(11) 0.0237(16) Uani 1 1 d D . .
H4 H 0.3036 0.7246 0.4880 0.028 Uiso 1 1 calc R . .
C5 C 0.3647(4) 0.67881(17) 0.2282(13) 0.0284(17) Uani 1 1 d D . .
H5 H 0.4493 0.6936 0.2328 0.034 Uiso 1 1 calc R . .
C6 C 0.3275(5) 0.63905(18) 0.0654(12) 0.0265(17) Uani 1 1 d D . .
H6 H 0.3851 0.6273 -0.0471 0.032 Uiso 1 1 calc R . .
C7 C 0.2069(5) 0.61664(16) 0.0671(13) 0.0286(16) Uani 1 1 d D . .
H7 H 0.1829 0.5889 -0.0397 0.034 Uiso 1 1 calc R . .
C8 C -0.1276(5) 0.63402(16) 0.1036(11) 0.0215(14) Uani 1 1 d D . .
C9 C -0.1596(5) 0.67518(16) 0.2282(11) 0.0242(15) Uani 1 1 d D . .
C10 C -0.0695(5) 0.69614(16) 0.4787(11) 0.0263(15) Uani 1 1 d D . .
H10 H -0.1133 0.7123 0.6032 0.032 Uiso 1 1 calc R . .
C11 C -0.2840(4) 0.69645(17) 0.1015(11) 0.0266(17) Uani 1 1 d D . .
H11 H -0.3111 0.7234 0.1871 0.032 Uiso 1 1 calc R . .
C12 C -0.3676(5) 0.67925(17) -0.1440(11) 0.0240(15) Uani 1 1 d D . .
H12 H -0.4497 0.6951 -0.2294 0.029 Uiso 1 1 calc R . .
C13 C -0.3338(5) 0.63927(17) -0.2677(12) 0.0269(17) Uani 1 1 d D . .
H13 H -0.3931 0.6271 -0.4347 0.032 Uiso 1 1 calc R . .
C14 C -0.2130(5) 0.61713(17) -0.1462(11) 0.0232(14) Uani 1 1 d D . .
H14 H -0.1876 0.5901 -0.2336 0.028 Uiso 1 1 calc R . .
C15 C 0.0032(5) 0.56663(7) 0.3440(5) 0.0238(5) Uani 1 1 d DU . .
O2 O 0.4138(4) 0.54758(15) 0.6503(13) 0.0398(13) Uani 1 1 d D . .
H1O H 0.472(2) 0.5543(15) 0.543(5) 0.048 Uiso 1 1 d D . .
H2O H 0.3284(12) 0.5551(11) 0.557(6) 0.048 Uiso 1 1 d D . .
O3 O 0.4208(4) 0.45140(14) 0.7638(12) 0.0445(13) Uani 1 1 d D . .
H3O H 0.445(4) 0.4496(16) 0.955(2) 0.053 Uiso 1 1 d D . .
H4O H 0.423(3) 0.4821(4) 0.732(8) 0.053 Uiso 1 1 d D . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0218(12) 0.0171(10) 0.0296(18) 0.0017(10) 0.008(3) -0.005(3)
N2 0.0245(15) 0.0153(14) 0.0285(18) 0.0013(13) 0.007(2) 0.0027(17)
O1 0.0271(18) 0.0265(17) 0.047(2) 0.0114(15) 0.007(2) 0.0030(16)
C1 0.016(3) 0.024(4) 0.020(3) 0.006(3) -0.001(3) 0.002(3)
C2 0.014(3) 0.031(3) 0.019(4) 0.007(3) 0.000(3) -0.003(2)
C3 0.024(3) 0.023(3) 0.018(3) -0.008(3) 0.003(3) 0.006(3)
C4 0.035(3) 0.015(3) 0.021(4) 0.001(3) 0.007(3) 0.005(3)
C5 0.018(3) 0.023(3) 0.043(5) 0.009(4) 0.005(4) 0.002(3)
C6 0.030(3) 0.029(4) 0.024(4) -0.003(3) 0.014(3) 0.000(3)
C7 0.034(3) 0.009(3) 0.041(4) 0.008(3) 0.005(3) 0.005(3)
C8 0.023(3) 0.014(3) 0.028(4) 0.002(3) 0.007(3) -0.001(3)
C9 0.035(3) 0.013(3) 0.025(4) 0.001(3) 0.009(3) -0.005(3)
C10 0.034(3) 0.019(3) 0.026(4) 0.010(3) 0.009(4) 0.004(3)
C11 0.015(3) 0.029(4) 0.038(5) 0.004(3) 0.012(3) 0.005(3)
C12 0.025(3) 0.027(4) 0.021(4) 0.005(4) 0.006(3) 0.002(3)
C13 0.022(3) 0.024(4) 0.033(4) 0.008(3) 0.005(3) -0.005(3)
C14 0.027(3) 0.027(3) 0.016(3) -0.005(3) 0.007(3) 0.001(3)
C15 0.0257(13) 0.0168(12) 0.0287(15) 0.0003(10) 0.006(2) 0.0027(19)
O2 0.038(2) 0.039(3) 0.040(3) 0.005(3) 0.006(2) 0.010(2)
O3 0.076(3) 0.025(2) 0.027(3) 0.002(3) 0.002(2) 0.000(2)

_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 C15 1.378(3) . ?
N1 C8 1.431(6) . ?
N1 C1 1.433(6) . ?
N2 C15 1.328(2) . ?
N2 H1N 0.878(10) . ?
N2 H2N 0.879(10) . ?
O1 C15 1.257(2) . ?
C1 C7 1.389(4) . ?
C1 C2 1.399(4) . ?
C2 C4 1.405(4) . ?
C2 C3 1.469(4) . ?
C3 C10 1.335(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.390(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.381(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C14 1.393(4) . ?
C8 C9 1.402(4) . ?
C9 C11 1.401(4) . ?
C9 C10 1.461(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.374(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
O2 H1O 0.895(8) . ?
O2 H2O 0.900(8) . ?
O3 H3O 0.899(8) . ?
O3 H4O 0.899(8) . ?

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
C15 N1 C8 123.6(4) . . ?
C15 N1 C1 119.7(4) . . ?
C8 N1 C1 116.64(17) . . ?
C15 N2 H1N 126.7(19) . . ?
C15 N2 H2N 114(2) . . ?
H1N N2 H2N 119(3) . . ?
C7 C1 C2 121.1(4) . . ?
C7 C1 N1 119.5(4) . . ?
C2 C1 N1 119.4(4) . . ?
C1 C2 C4 117.5(4) . . ?
C1 C2 C3 123.0(4) . . ?
C4 C2 C3 119.5(4) . . ?
C10 C3 C2 125.1(6) . . ?
C10 C3 H3 117.4 . . ?
C2 C3 H3 117.4 . . ?
C5 C4 C2 121.5(4) . . ?
C5 C4 H4 119.2 . . ?
C2 C4 H4 119.2 . . ?
C4 C5 C6 119.8(4) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 120.1(4) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C1 119.9(4) . . ?
C6 C7 H7 120.0 . . ?
C1 C7 H7 120.0 . . ?
C14 C8 C9 120.6(4) . . ?
C14 C8 N1 120.3(4) . . ?
C9 C8 N1 119.0(3) . . ?
C11 C9 C8 117.2(4) . . ?
C11 C9 C10 119.8(4) . . ?
C8 C9 C10 123.0(4) . . ?
C3 C10 C9 128.4(6) . . ?
C3 C10 H10 115.8 . . ?
C9 C10 H10 115.8 . . ?
C12 C11 C9 121.5(4) . . ?
C12 C11 H11 119.3 . . ?
C9 C11 H11 119.3 . . ?
C11 C12 C13 120.7(4) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 119.2(4) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C8 120.6(4) . . ?
C13 C14 H14 119.7 . . ?
C8 C14 H14 119.7 . . ?
O1 C15 N2 122.5(2) . . ?
O1 C15 N1 121.4(4) . . ?
N2 C15 N1 116.1(4) . . ?
H1O O2 H2O 109.8(14) . . ?
H3O O3 H4O 103(4) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.054


