# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2013


#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
# 
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material 
#  of the CCDC or of third parties, and may not be copied or further 
#  disseminated in any form, whether machine-readable or not,  
#  except for the purpose of generating routine backup copies 
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and 
#  data retrieval see:
#                         www.ccdc.cam.ac.uk 
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively. 
#
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data_sar05
_database_code_depnum_ccdc_archive 'CCDC 726213'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            'carbamazepine hemikis(fumaric acid)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 N2 O, 0.5(C4 H4 O4)'
_chemical_formula_sum            'C17 H14 N2 O3'
_chemical_formula_weight         294.30
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   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                   5.0356(3)
_cell_length_b                   9.3352(6)
_cell_length_c                   31.222(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.442(3)
_cell_angle_gamma                90.00
_cell_volume                     1465.02(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9556
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      28.29
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9215
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_process_details   
;
See Sheldrick, G. M. (2002). SADABS.
University of Gottingen, Germany.
;
_exptl_special_details           
;
The crystal temperature was held constant
using an Oxford Cryosystems
Cryostream 600 system.
;
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         
;
Bruker Nonius FR591 rotating anode generator
;
_diffrn_radiation_monochromator  
;
graphite model mounted in "parallel" mode
;
_diffrn_measurement_device_type  
;
Mach3 kappa-type 4-circle goniostat.
;
_diffrn_radiation_detector       'ApexII camera'
_diffrn_measurement_method       'rotation images'
_diffrn_detector_area_resol_mean 
;
120 microns
;
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            24013
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3338
_reflns_number_gt                2693
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       
;
APEX 2 software, Bruker Nonius 2004
;
_computing_cell_refinement       
;
APEX 2 software, Bruker Nonius 2004
;
_computing_data_reduction        
;
SAINT - Bruker Integration program embedded in
APEX 2 software, Bruker Nonius 2004
;
_computing_structure_solution    
;
SHELXS-97 (Sheldrick, G. M. Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.)
;
_computing_structure_refinement  
;
SHELXL-97 (Sheldrick, G. M. Acta Cryst. (2008). A64, 112)
XSeed (L.J.Barbour, J.Supramol. Chem., 2003, 1, 189.)
;
_computing_molecular_graphics    'ORTEP-III Version 1.08 (Farrugia, 2005)'
_computing_publication_material  
;
enCIFer: A program for viewing, editing and visualising CIFs.
F. H. Allen, O. Johnson, G. P. Shields, B. R. Smith, M. Towler,
J. Applied Cryst., 37, 331-334, 2004
;
_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^)+(0.0344P)^2^+0.6861P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3338
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0944
_refine_ls_wR_factor_gt          0.0840
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
O1 O 0.28137(19) 0.27920(10) 0.08559(3) 0.0268(2) Uani 1 1 d . . .
N1 N 0.1073(2) 0.08268(11) 0.11711(3) 0.0205(2) Uani 1 1 d . . .
C1 C 0.0451(3) -0.06885(13) 0.11801(4) 0.0198(3) Uani 1 1 d . . .
N2 N 0.2605(2) 0.06906(12) 0.04758(3) 0.0253(3) Uani 1 1 d . . .
H2B H 0.3319 0.1085 0.0254 0.030 Uiso 1 1 calc R . .
H2A H 0.2153 -0.0220 0.0468 0.030 Uiso 1 1 calc R . .
C2 C -0.1737(3) -0.12128(14) 0.09272(4) 0.0236(3) Uani 1 1 d . . .
H2 H -0.2808 -0.0575 0.0754 0.028 Uiso 1 1 calc R . .
C3 C -0.2336(3) -0.26747(15) 0.09307(5) 0.0288(3) Uani 1 1 d . . .
H3 H -0.3820 -0.3032 0.0761 0.035 Uiso 1 1 calc R . .
C4 C -0.0742(3) -0.36105(15) 0.11848(5) 0.0336(3) Uani 1 1 d . . .
H4 H -0.1131 -0.4606 0.1184 0.040 Uiso 1 1 calc R . .
C5 C 0.1411(3) -0.30881(15) 0.14384(5) 0.0310(3) Uani 1 1 d . . .
H5 H 0.2475 -0.3736 0.1609 0.037 Uiso 1 1 calc R . .
C6 C 0.2051(3) -0.16047(14) 0.14473(4) 0.0220(3) Uani 1 1 d . . .
C7 C 0.4287(3) -0.10789(15) 0.17324(4) 0.0245(3) Uani 1 1 d . . .
H7 H 0.5781 -0.1696 0.1773 0.029 Uiso 1 1 calc R . .
C8 C 0.4432(3) 0.01887(15) 0.19421(4) 0.0247(3) Uani 1 1 d . . .
H8 H 0.6018 0.0371 0.2114 0.030 Uiso 1 1 calc R . .
C9 C 0.2377(3) 0.13172(14) 0.19315(4) 0.0228(3) Uani 1 1 d . . .
C10 C 0.2005(3) 0.21262(16) 0.23070(5) 0.0312(3) Uani 1 1 d . . .
H10 H 0.3130 0.1957 0.2557 0.037 Uiso 1 1 calc R . .
C11 C 0.0020(3) 0.31655(16) 0.23168(5) 0.0340(3) Uani 1 1 d . . .
H11 H -0.0200 0.3696 0.2572 0.041 Uiso 1 1 calc R . .
C12 C -0.1651(3) 0.34260(15) 0.19494(5) 0.0322(3) Uani 1 1 d . . .
H12 H -0.3010 0.4130 0.1956 0.039 Uiso 1 1 calc R . .
C13 C -0.1320(3) 0.26507(14) 0.15724(5) 0.0263(3) Uani 1 1 d . . .
H13 H -0.2459 0.2823 0.1324 0.032 Uiso 1 1 calc R . .
C14 C 0.0699(3) 0.16194(13) 0.15627(4) 0.0204(3) Uani 1 1 d . . .
C15 C 0.2200(2) 0.14874(13) 0.08300(4) 0.0199(3) Uani 1 1 d . . .
C21 C 0.0380(3) 0.93513(15) 0.50572(4) 0.0273(3) Uani 1 1 d . . .
H21 H -0.0555 0.8895 0.5275 0.033 Uiso 1 1 calc R . .
O22 O 0.3299(2) 0.73430(10) 0.50126(3) 0.0323(2) Uani 1 1 d . . .
C22 C 0.2600(3) 0.85306(14) 0.48727(4) 0.0224(3) Uani 1 1 d . . .
O23 O 0.37180(19) 0.91979(10) 0.45547(3) 0.0254(2) Uani 1 1 d . . .
H23 H 0.4840 0.8654 0.4450 0.031 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
O1 0.0326(5) 0.0182(5) 0.0310(5) 0.0025(4) 0.0127(4) -0.0029(4)
N1 0.0271(6) 0.0160(5) 0.0187(5) 0.0006(4) 0.0042(4) -0.0032(4)
C1 0.0246(6) 0.0161(6) 0.0197(6) -0.0006(5) 0.0084(5) -0.0021(5)
N2 0.0335(6) 0.0222(6) 0.0211(6) 0.0017(4) 0.0082(5) -0.0024(5)
C2 0.0243(7) 0.0237(7) 0.0233(6) -0.0031(5) 0.0054(5) -0.0007(5)
C3 0.0317(7) 0.0285(7) 0.0270(7) -0.0092(6) 0.0089(6) -0.0098(6)
C4 0.0525(10) 0.0186(7) 0.0307(8) -0.0031(6) 0.0102(7) -0.0104(6)
C5 0.0463(9) 0.0198(7) 0.0274(7) 0.0039(5) 0.0050(6) 0.0019(6)
C6 0.0268(7) 0.0202(6) 0.0196(6) 0.0008(5) 0.0070(5) 0.0000(5)
C7 0.0253(7) 0.0264(7) 0.0220(6) 0.0049(5) 0.0038(5) 0.0037(5)
C8 0.0224(6) 0.0312(7) 0.0205(6) 0.0007(5) 0.0015(5) -0.0035(5)
C9 0.0240(7) 0.0221(6) 0.0228(6) -0.0016(5) 0.0062(5) -0.0069(5)
C10 0.0362(8) 0.0333(8) 0.0245(7) -0.0071(6) 0.0051(6) -0.0056(6)
C11 0.0430(9) 0.0296(8) 0.0309(8) -0.0108(6) 0.0142(7) -0.0060(6)
C12 0.0344(8) 0.0205(7) 0.0433(9) -0.0050(6) 0.0143(6) -0.0003(6)
C13 0.0288(7) 0.0187(6) 0.0318(7) 0.0013(5) 0.0053(6) -0.0020(5)
C14 0.0250(6) 0.0154(6) 0.0215(6) -0.0003(5) 0.0071(5) -0.0069(5)
C15 0.0181(6) 0.0203(6) 0.0214(6) 0.0037(5) 0.0024(5) 0.0011(5)
C21 0.0290(7) 0.0275(7) 0.0265(7) 0.0039(5) 0.0121(6) 0.0052(5)
O22 0.0391(6) 0.0244(5) 0.0348(6) 0.0071(4) 0.0143(5) 0.0099(4)
C22 0.0239(6) 0.0213(6) 0.0223(6) -0.0005(5) 0.0042(5) 0.0016(5)
O23 0.0271(5) 0.0237(5) 0.0267(5) 0.0027(4) 0.0119(4) 0.0082(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
O1 C15 1.2578(15) . ?
N1 C15 1.3818(16) . ?
N1 C1 1.4496(15) . ?
N1 C14 1.4509(16) . ?
C1 C2 1.4043(19) . ?
C1 C6 1.4130(18) . ?
N2 C15 1.3583(16) . ?
N2 H2B 0.8800 . ?
N2 H2A 0.8800 . ?
C2 C3 1.3978(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.400(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.4217(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.4766(19) . ?
C7 C8 1.3523(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.4756(19) . ?
C8 H8 0.9500 . ?
C9 C14 1.4150(19) . ?
C9 C10 1.4165(18) . ?
C10 C11 1.395(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.402(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.400(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.4018(19) . ?
C13 H13 0.9500 . ?
C21 C21 1.313(3) 3_576 ?
C21 C22 1.4984(18) . ?
C21 H21 0.9500 . ?
O22 C22 1.2351(16) . ?
C22 O23 1.3259(15) . ?
O23 H23 0.8400 . ?
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 C1 123.34(10) . . ?
C15 N1 C14 120.13(10) . . ?
C1 N1 C14 116.25(10) . . ?
C2 C1 C6 121.43(12) . . ?
C2 C1 N1 119.51(12) . . ?
C6 C1 N1 119.06(11) . . ?
C15 N2 H2B 120.0 . . ?
C15 N2 H2A 120.0 . . ?
H2B N2 H2A 120.0 . . ?
C3 C2 C1 119.87(13) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 119.81(13) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.28(13) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 121.35(13) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 117.23(12) . . ?
C1 C6 C7 122.82(12) . . ?
C5 C6 C7 119.95(12) . . ?
C8 C7 C6 126.86(12) . . ?
C8 C7 H7 116.6 . . ?
C6 C7 H7 116.6 . . ?
C7 C8 C9 126.62(12) . . ?
C7 C8 H8 116.7 . . ?
C9 C8 H8 116.7 . . ?
C14 C9 C10 117.72(13) . . ?
C14 C9 C8 122.96(11) . . ?
C10 C9 C8 119.31(12) . . ?
C11 C10 C9 121.30(14) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 119.90(13) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 120.13(14) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 119.76(13) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C9 121.17(12) . . ?
C13 C14 N1 119.96(12) . . ?
C9 C14 N1 118.87(11) . . ?
O1 C15 N2 122.29(11) . . ?
O1 C15 N1 119.55(11) . . ?
N2 C15 N1 118.16(11) . . ?
C21 C21 C22 125.37(16) 3_576 . ?
C21 C21 H21 117.3 3_576 . ?
C22 C21 H21 117.3 . . ?
O22 C22 O23 124.15(12) . . ?
O22 C22 C21 121.78(12) . . ?
O23 C22 C21 114.06(11) . . ?
C22 O23 H23 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
C15 N1 C1 C2 -73.71(16) . . . . ?
C14 N1 C1 C2 112.33(13) . . . . ?
C15 N1 C1 C6 106.88(14) . . . . ?
C14 N1 C1 C6 -67.08(15) . . . . ?
C6 C1 C2 C3 -1.22(19) . . . . ?
N1 C1 C2 C3 179.38(11) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C2 C3 C4 C5 1.0(2) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C2 C1 C6 C5 2.10(18) . . . . ?
N1 C1 C6 C5 -178.50(11) . . . . ?
C2 C1 C6 C7 -177.04(12) . . . . ?
N1 C1 C6 C7 2.36(18) . . . . ?
C4 C5 C6 C1 -1.5(2) . . . . ?
C4 C5 C6 C7 177.68(13) . . . . ?
C1 C6 C7 C8 34.1(2) . . . . ?
C5 C6 C7 C8 -144.99(14) . . . . ?
C6 C7 C8 C9 0.2(2) . . . . ?
C7 C8 C9 C14 -34.3(2) . . . . ?
C7 C8 C9 C10 144.45(14) . . . . ?
C14 C9 C10 C11 1.3(2) . . . . ?
C8 C9 C10 C11 -177.52(13) . . . . ?
C9 C10 C11 C12 -0.1(2) . . . . ?
C10 C11 C12 C13 -0.4(2) . . . . ?
C11 C12 C13 C14 -0.4(2) . . . . ?
C12 C13 C14 C9 1.67(19) . . . . ?
C12 C13 C14 N1 -179.18(12) . . . . ?
C10 C9 C14 C13 -2.08(18) . . . . ?
C8 C9 C14 C13 176.69(12) . . . . ?
C10 C9 C14 N1 178.76(11) . . . . ?
C8 C9 C14 N1 -2.47(18) . . . . ?
C15 N1 C14 C13 73.85(16) . . . . ?
C1 N1 C14 C13 -111.99(13) . . . . ?
C15 N1 C14 C9 -106.98(13) . . . . ?
C1 N1 C14 C9 67.18(15) . . . . ?
C1 N1 C15 O1 -176.19(12) . . . . ?
C14 N1 C15 O1 -2.46(18) . . . . ?
C1 N1 C15 N2 3.83(18) . . . . ?
C14 N1 C15 N2 177.56(11) . . . . ?
C21 C21 C22 O22 175.97(19) 3_576 . . . ?
C21 C21 C22 O23 -3.5(3) 3_576 . . . ?
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.041
################################END_OF_FILE###