# Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Alastair Florence'
_publ_contact_author_email       ALASTAIR.FLORENCE@STRATH.AC.UK

_publ_section_title              
;
A Predicted Dimer-based Polymorph of
10,11-Dihydrocarbamazepine (Form IV)
;
loop_
_publ_author_name
'Alastair Florence'
'Jean-Baptiste Arlin'
'Andrea Johnston'
'Alan R. Kennedy'
'Gary Miller'
;
S.L.Price
;

# Attachment 'DHC-FormIV-Final.cif'

data_Dihydrocarbamazepine_form_IV_SX_structure
_database_code_depnum_ccdc_archive 'CCDC 739821'

_chemical_name_systematic        
10,11-Dihydro-5H-dibenzo(b,f)azepine-5-carboxamide

_chemical_name_common            
10,11-Dihydro-5H-dibenzo(b,f)azepine-5-carboxamide
_chemical_formula_sum            'C15 H14 N2 O'
_chemical_formula_moiety         'C15 H14 N2 O'
_chemical_formula_weight         238.28

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   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   13.207(6)
_cell_length_b                   5.347(2)
_cell_length_c                   18.891(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.37(2)
_cell_angle_gamma                90.00
_cell_volume                     1195.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    1650
_cell_measurement_theta_min      3.21
_cell_measurement_theta_max      24.86

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_preparation       sublimation
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9660
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
This is a polymorph of dihydrocarbamazepine, termed form IV.
;

_diffrn_ambient_temperature      123(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16837
_diffrn_reflns_av_R_equivalents  0.0824
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2353
_reflns_number_gt                1566
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0440P)²+0.1319P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2353
_refine_ls_number_parameters     171
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.0983
_refine_ls_wR_factor_gt          0.0840
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
C1 C 0.77324(15) 0.0123(3) 0.04367(10) 0.0184(4) Uani 1 1 d . . .
C2 C 0.76153(15) 0.1996(3) 0.09097(10) 0.0227(4) Uani 1 1 d . . .
H1 H 0.6888 0.2663 0.0783 0.027 Uiso 1 1 calc R . .
C3 C 0.85463(15) 0.2892(4) 0.15608(10) 0.0248(4) Uani 1 1 d . . .
H2 H 0.8458 0.4140 0.1887 0.030 Uiso 1 1 calc R . .
C4 C 0.96094(16) 0.1957(3) 0.17339(11) 0.0252(4) Uani 1 1 d . . .
H3 H 1.0256 0.2575 0.2176 0.030 Uiso 1 1 calc R . .
C5 C 0.97231(16) 0.0121(3) 0.12597(10) 0.0229(4) Uani 1 1 d . . .
H4 H 1.0457 -0.0496 0.1383 0.027 Uiso 1 1 calc R . .
C6 C 0.87968(15) -0.0863(3) 0.06045(10) 0.0184(4) Uani 1 1 d . . .
C7 C 0.90431(15) -0.2900(3) 0.01426(10) 0.0227(4) Uani 1 1 d . . .
H5 H 0.9465 -0.4242 0.0520 0.027 Uiso 1 1 calc R . .
H6 H 0.9557 -0.2185 -0.0058 0.027 Uiso 1 1 calc R . .
C8 C 0.80518(15) -0.4127(3) -0.05575(10) 0.0233(4) Uani 1 1 d . . .
H7 H 0.8349 -0.5404 -0.0796 0.028 Uiso 1 1 calc R . .
H8 H 0.7560 -0.4986 -0.0363 0.028 Uiso 1 1 calc R . .
C9 C 0.73608(14) -0.2268(3) -0.11795(10) 0.0188(4) Uani 1 1 d . . .
C10 C 0.73414(15) -0.2144(4) -0.19213(10) 0.0242(4) Uani 1 1 d . . .
H9 H 0.7767 -0.3310 -0.2060 0.029 Uiso 1 1 calc R . .
C11 C 0.67036(15) -0.0324(4) -0.24610(11) 0.0260(5) Uani 1 1 d . . .
H10 H 0.6699 -0.0253 -0.2965 0.031 Uiso 1 1 calc R . .
C12 C 0.60757(16) 0.1383(4) -0.22721(11) 0.0253(5) Uani 1 1 d . . .
H11 H 0.5640 0.2619 -0.2644 0.030 Uiso 1 1 calc R . .
C13 C 0.60856(15) 0.1280(3) -0.15360(10) 0.0219(4) Uani 1 1 d . . .
H12 H 0.5663 0.2455 -0.1398 0.026 Uiso 1 1 calc R . .
C14 C 0.67148(15) -0.0547(3) -0.10034(10) 0.0177(4) Uani 1 1 d . . .
C15 C 0.59446(14) -0.2233(3) -0.01579(10) 0.0191(4) Uani 1 1 d . . .
N1 N 0.67287(12) -0.0699(3) -0.02364(8) 0.0180(4) Uani 1 1 d . . .
N2 N 0.59931(13) -0.2466(3) 0.05591(9) 0.0221(4) Uani 1 1 d D . .
O1 O 0.52238(10) -0.3361(2) -0.07474(7) 0.0260(3) Uani 1 1 d . . .
H13 H 0.5515(14) -0.359(3) 0.0599(12) 0.042(6) Uiso 1 1 d D . .
H14 H 0.6484(15) -0.152(4) 0.0953(9) 0.058(7) Uiso 1 1 d D . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.396(2) . ?
C1 C6 1.400(3) . ?
C1 N1 1.439(2) . ?
C2 C3 1.382(2) . ?
C2 H1 0.9500 . ?
C3 C4 1.386(3) . ?
C3 H2 0.9500 . ?
C4 C5 1.381(3) . ?
C4 H3 0.9500 . ?
C5 C6 1.400(2) . ?
C5 H4 0.9500 . ?
C6 C7 1.518(2) . ?
C7 C8 1.535(2) . ?
C7 H5 0.9900 . ?
C7 H6 0.9900 . ?
C8 C9 1.499(2) . ?
C8 H7 0.9900 . ?
C8 H8 0.9900 . ?
C9 C10 1.392(2) . ?
C9 C14 1.392(2) . ?
C10 C11 1.390(3) . ?
C10 H9 0.9500 . ?
C11 C12 1.383(3) . ?
C11 H10 0.9500 . ?
C12 C13 1.386(2) . ?
C12 H11 0.9500 . ?
C13 C14 1.384(2) . ?
C13 H12 0.9500 . ?
C14 N1 1.443(2) . ?
C15 O1 1.252(2) . ?
C15 N2 1.333(2) . ?
C15 N1 1.380(2) . ?
N2 H13 0.898(5) . ?
N2 H14 0.896(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.73(16) . . ?
C2 C1 N1 117.68(16) . . ?
C6 C1 N1 121.57(16) . . ?
C3 C2 C1 120.71(17) . . ?
C3 C2 H1 119.6 . . ?
C1 C2 H1 119.6 . . ?
C2 C3 C4 119.49(18) . . ?
C2 C3 H2 120.3 . . ?
C4 C3 H2 120.3 . . ?
C5 C4 C3 119.61(17) . . ?
C5 C4 H3 120.2 . . ?
C3 C4 H3 120.2 . . ?
C4 C5 C6 122.43(18) . . ?
C4 C5 H4 118.8 . . ?
C6 C5 H4 118.8 . . ?
C1 C6 C5 117.00(17) . . ?
C1 C6 C7 126.15(15) . . ?
C5 C6 C7 116.84(16) . . ?
C6 C7 C8 118.91(15) . . ?
C6 C7 H5 107.6 . . ?
C8 C7 H5 107.6 . . ?
C6 C7 H6 107.6 . . ?
C8 C7 H6 107.6 . . ?
H5 C7 H6 107.0 . . ?
C9 C8 C7 112.41(15) . . ?
C9 C8 H7 109.1 . . ?
C7 C8 H7 109.1 . . ?
C9 C8 H8 109.1 . . ?
C7 C8 H8 109.1 . . ?
H7 C8 H8 107.9 . . ?
C10 C9 C14 118.04(16) . . ?
C10 C9 C8 123.59(17) . . ?
C14 C9 C8 118.37(16) . . ?
C11 C10 C9 120.39(18) . . ?
C11 C10 H9 119.8 . . ?
C9 C10 H9 119.8 . . ?
C12 C11 C10 120.69(18) . . ?
C12 C11 H10 119.7 . . ?
C10 C11 H10 119.7 . . ?
C11 C12 C13 119.55(18) . . ?
C11 C12 H11 120.2 . . ?
C13 C12 H11 120.2 . . ?
C14 C13 C12 119.52(18) . . ?
C14 C13 H12 120.2 . . ?
C12 C13 H12 120.2 . . ?
C13 C14 C9 121.79(16) . . ?
C13 C14 N1 120.37(16) . . ?
C9 C14 N1 117.84(15) . . ?
O1 C15 N2 122.20(16) . . ?
O1 C15 N1 120.07(16) . . ?
N2 C15 N1 117.73(15) . . ?
C15 N1 C1 121.84(14) . . ?
C15 N1 C14 117.78(14) . . ?
C1 N1 C14 117.77(14) . . ?
C15 N2 H13 115.4(14) . . ?
C15 N2 H14 118.8(15) . . ?
H13 N2 H14 126(2) . . ?

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
C6 C1 C2 C3 -1.0(3) . . . . ?
N1 C1 C2 C3 -179.32(16) . . . . ?
C1 C2 C3 C4 1.5(3) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C2 C1 C6 C5 -0.2(2) . . . . ?
N1 C1 C6 C5 178.08(15) . . . . ?
C2 C1 C6 C7 179.82(17) . . . . ?
N1 C1 C6 C7 -1.9(3) . . . . ?
C4 C5 C6 C1 0.9(3) . . . . ?
C4 C5 C6 C7 -179.14(17) . . . . ?
C1 C6 C7 C8 -2.9(3) . . . . ?
C5 C6 C7 C8 177.18(16) . . . . ?
C6 C7 C8 C9 58.7(2) . . . . ?
C7 C8 C9 C10 110.0(2) . . . . ?
C7 C8 C9 C14 -69.0(2) . . . . ?
C14 C9 C10 C11 0.8(3) . . . . ?
C8 C9 C10 C11 -178.23(16) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
C11 C12 C13 C14 -0.7(3) . . . . ?
C12 C13 C14 C9 1.3(3) . . . . ?
C12 C13 C14 N1 -179.48(16) . . . . ?
C10 C9 C14 C13 -1.4(2) . . . . ?
C8 C9 C14 C13 177.75(16) . . . . ?
C10 C9 C14 N1 179.39(15) . . . . ?
C8 C9 C14 N1 -1.5(2) . . . . ?
O1 C15 N1 C1 -164.03(16) . . . . ?
N2 C15 N1 C1 15.6(2) . . . . ?
O1 C15 N1 C14 -2.8(2) . . . . ?
N2 C15 N1 C14 176.83(16) . . . . ?
C2 C1 N1 C15 -75.4(2) . . . . ?
C6 C1 N1 C15 106.2(2) . . . . ?
C2 C1 N1 C14 123.30(18) . . . . ?
C6 C1 N1 C14 -55.1(2) . . . . ?
C13 C14 N1 C15 91.9(2) . . . . ?
C9 C14 N1 C15 -88.84(19) . . . . ?
C13 C14 N1 C1 -106.07(19) . . . . ?
C9 C14 N1 C1 73.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.045


