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
loop_
_publ_author_name
_publ_author_address
A.J.Florence
;
Solid-State Research Group,
Strathclyde Institute of Pharmacy and Biomedical Sciences,
University of Strathclyde,
27 Taylor Street,
Glasgow G4 0NR,
Scotland.
;
C.Bedford
;
Department of Chemistry,
University College London,
20 Gordon St,
London WC1H 0AJ,
England.
;
'Francesca P. A. Fabbiani'
;
ISIS Facility,
Rutherford Appleton Laboratory,
Chilton, Didcot,
Oxon OX11 0QX,
England.
;
K.Shankland
;
ISIS Facility,
Rutherford Appleton Laboratory,
Chilton, Didcot,
Oxon OX11 0QX,
England.
;
T.Gelbrich
;
School of Chemistry,
University of Southampton, Highfield,
Southampton SO17 1BJ,
England.
;
;
M.B.Hursthouse
;
;
School of Chemistry,
University of Southampton, Highfield,
Southampton SO17 1BJ,
England.
;
N.Shankland
;
Solid-State Research Group,
Strathclyde Institute of Pharmacy and Biomedical Sciences,
University of Strathclyde,
27 Taylor Street,
Glasgow G4 0NR,
Scotland.
;
A.Johnston
;
Solid-State Research Group,
Strathclyde Institute of Pharmacy and Biomedical Sciences,
University of Strathclyde,
27 Taylor Street,
Glasgow G4 0NR,
Scotland.
;
P.Fernandes
;
Solid-State Research Group,
Strathclyde Institute of Pharmacy and Biomedical Sciences,
University of Strathclyde,
27 Taylor Street,
Glasgow G4 0NR,
Scotland.
;
_publ_contact_author_address     
;
Solid-State Research Group,
Strathclyde Institute of Pharmacy and Biomedical Sciences,
University of Strathclyde,
27 Taylor Street,
Glasgow G4 0NR,
Scotland.
;
_publ_contact_author_email       alastair.florence@strath.ac.uk
_publ_contact_author_fax         +44(0)1415522562
_publ_contact_author_phone       +44(0)1415484877

_publ_contact_author_name        'Prof.  Alastair Florence'
#==============================================================================

# 1. SUBMISSION DETAILS

_publ_section_title              
;Two-dimensional similarity between forms I and II of
cytenamide, a carbamazepine analogue
;

data_cytenamide_form_II_triclinic_powder_structure
_database_code_depnum_ccdc_archive 'CCDC 672212'

_chemical_name_systematic        
;
5H-Dibenzo[a,d]cycloheptene-5-carboxamide
;
_chemical_name_common            'Cytenamide form II'
_chemical_formula_sum            'C16 H13 N1 O1'
_chemical_formula_moiety         'C16 H13 N1 O1'
_chemical_formula_weight         235.27
_chemical_melting_point          ?
_chemical_compound_source        
;
5H-Dibenzo[a,d]cyclohepten-5-one (Sigma-Aldrich) was converted by sodium
borohydride reduction in methanol into 5H-dibenzo[a,d]cycloheptenyl-5-ol. This
alcohol was converted by literature methods sequentially into the corresponding
5-chloro compound, the 5-cyano compound and the corresponding amide, 5H-
dibenzo[a,d]cycloheptene-5-carboxamide (cytenamide).
;

_exptl_crystal_description       'Polycrystalline powder'
_exptl_crystal_colour            Colourless
_exptl_crystal_preparation       
;
A sample of form I cytenamide (obtained by recrystallisation from chloroform)
was heated to a maximum temperature of 498 K in a rotating 0.7 mm borosilicate
glass capillary, mounted on Bruker AXS D8 Discover TXS X-ray powder
diffractometer, thereby transforming it to form II. The sample of form II
cytenamide was then cooled to room temperature and held there for the duration
of the data collection. The precise transformation temperature was not
determined from this experiment.
;

_cell_length_a                   5.8100(2)
_cell_length_b                   19.6315(5)
_cell_length_c                   21.7087(6)
_cell_angle_alpha                85.918(2)
_cell_angle_beta                 86.164(2)
_cell_angle_gamma                84.482(2)
_cell_volume                     2453.82(13)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_formula_units_Z            8
_cell_measurement_temperature    293
_exptl_crystal_density_diffrn    1.274
_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Cu K\a~1~'
_diffrn_radiation_wavelength     1.54056
_diffrn_measurement_device_type  
;
Bruker AXS D8 Discover TXS X-ray powder diffractometer
;
_pd_proc_ls_prof_R_factor        0.034
_pd_proc_ls_prof_wR_factor       0.040
_pd_proc_ls_prof_wR_expected     0.013
_refine_ls_goodness_of_fit_all   3.08

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O1A O Uiso 0.47637 0.69896 0.34574 1.000 0.0485(16) . G
N1A N Uiso 0.49509 0.62336 0.42710 1.000 0.0485(16) . G
C1A C Uiso 0.20865 0.61031 0.34700 1.000 0.0485(16) . G
C2A C Uiso 0.39543 0.64858 0.37236 1.000 0.0485(16) . G
C3A C Uiso 0.19624 0.61859 0.27786 1.000 0.0485(16) . G
C4A C Uiso -0.00356 0.65339 0.25405 1.000 0.0485(16) . G
C5A C Uiso -0.02712 0.66215 0.19076 1.000 0.0485(16) . G
C6A C Uiso 0.14984 0.63613 0.15005 1.000 0.0485(16) . G
C7A C Uiso 0.34868 0.60157 0.17297 1.000 0.0485(16) . G
C8A C Uiso 0.37358 0.59205 0.23686 1.000 0.0485(16) . G
C9A C Uiso 0.58715 0.55484 0.25745 1.000 0.0485(16) . G
C10A C Uiso 0.60490 0.50992 0.30665 1.000 0.0485(16) . G
C11A C Uiso 0.41403 0.48958 0.34885 1.000 0.0485(16) . G
C12A C Uiso 0.42158 0.42059 0.37103 1.000 0.0485(16) . G
C13A C Uiso 0.24577 0.39742 0.41107 1.000 0.0485(16) . G
C14A C Uiso 0.06037 0.44300 0.43007 1.000 0.0485(16) . G
C15A C Uiso 0.05217 0.51147 0.40883 1.000 0.0485(16) . G
C16A C Uiso 0.22809 0.53548 0.36814 1.000 0.0485(16) . G
O1B O Uiso 0.20363 0.28627 0.53982 1.000 0.0485(16) . G
N1B N Uiso 0.20389 0.22192 0.62850 1.000 0.0485(16) . G
C1B C Uiso -0.07770 0.20087 0.54954 1.000 0.0485(16) . G
C2B C Uiso 0.11273 0.24056 0.57124 1.000 0.0485(16) . G
C3B C Uiso -0.07933 0.19841 0.48048 1.000 0.0485(16) . G
C4B C Uiso -0.26973 0.23177 0.45096 1.000 0.0485(16) . G
C5B C Uiso -0.28323 0.23084 0.38750 1.000 0.0485(16) . G
C6B C Uiso -0.10543 0.19638 0.35235 1.000 0.0485(16) . G
C7B C Uiso 0.08417 0.16313 0.38096 1.000 0.0485(16) . G
C8B C Uiso 0.09878 0.16339 0.44512 1.000 0.0485(16) . G
C9B C Uiso 0.30295 0.12696 0.47190 1.000 0.0485(16) . G
C10B C Uiso 0.30595 0.08980 0.52604 1.000 0.0485(16) . G
C11B C Uiso 0.10562 0.07859 0.56839 1.000 0.0485(16) . G
C12B C Uiso 0.09766 0.01339 0.59896 1.000 0.0485(16) . G
C13B C Uiso -0.08783 -0.00116 0.63967 1.000 0.0485(16) . G
C14B C Uiso -0.26760 0.04945 0.65096 1.000 0.0485(16) . G
C15B C Uiso -0.26052 0.11428 0.62137 1.000 0.0485(16) . G
C16B C Uiso -0.07468 0.12957 0.57992 1.000 0.0485(16) . G
O1C O Uiso 0.29525 0.55638 1.01602 1.000 0.0485(16) . G
N1C N Uiso 0.33963 0.51474 0.92279 1.000 0.0485(16) . G
C1C C Uiso -0.00678 0.59901 0.94638 1.000 0.0485(16) . G
C2C C Uiso 0.21254 0.55540 0.96558 1.000 0.0485(16) . G
C3C C Uiso -0.05899 0.66417 0.97920 1.000 0.0485(16) . G
C4C C Uiso -0.25899 0.67044 1.01881 1.000 0.0485(16) . G
C5C C Uiso -0.31850 0.72948 1.04995 1.000 0.0485(16) . G
C6C C Uiso -0.17803 0.78346 1.04195 1.000 0.0485(16) . G
C7C C Uiso 0.02057 0.77796 1.00288 1.000 0.0485(16) . G
C8C C Uiso 0.08145 0.71870 0.97088 1.000 0.0485(16) . G
C9C C Uiso 0.29220 0.71686 0.93035 1.000 0.0485(16) . G
C10C C Uiso 0.32153 0.68962 0.87525 1.000 0.0485(16) . G
C11C C Uiso 0.14816 0.65679 0.84529 1.000 0.0485(16) . G
C12C C Uiso 0.14001 0.66834 0.78093 1.000 0.0485(16) . G
C13C C Uiso -0.02084 0.63910 0.74929 1.000 0.0485(16) . G
C14C C Uiso -0.17497 0.59726 0.78140 1.000 0.0485(16) . G
C15C C Uiso -0.16711 0.58502 0.84498 1.000 0.0485(16) . G
C16C C Uiso -0.00619 0.61449 0.87755 1.000 0.0485(16) . G
O1D O Uiso 0.20063 0.05240 0.96363 1.000 0.0485(16) . G
N1D N Uiso 0.20108 -0.06018 0.95653 1.000 0.0485(16) . G
C1D C Uiso 0.51180 0.00202 0.89523 1.000 0.0485(16) . G
C2D C Uiso 0.29443 0.00167 0.93907 1.000 0.0485(16) . G
C3D C Uiso 0.54552 -0.05629 0.85322 1.000 0.0485(16) . G
C4D C Uiso 0.73646 -0.10458 0.86115 1.000 0.0485(16) . G
C5D C Uiso 0.77896 -0.15916 0.82353 1.000 0.0485(16) . G
C6D C Uiso 0.63022 -0.16639 0.77716 1.000 0.0485(16) . G
C7D C Uiso 0.44045 -0.11897 0.76879 1.000 0.0485(16) . G
C8D C Uiso 0.39679 -0.06337 0.80629 1.000 0.0485(16) . G
C9D C Uiso 0.19450 -0.01542 0.79446 1.000 0.0485(16) . G
C10D C Uiso 0.18234 0.05273 0.79726 1.000 0.0485(16) . G
C11D C Uiso 0.36918 0.09193 0.81253 1.000 0.0485(16) . G
C12D C Uiso 0.39013 0.15558 0.78000 1.000 0.0485(16) . G
C13D C Uiso 0.56416 0.19556 0.79179 1.000 0.0485(16) . G
C14D C Uiso 0.71900 0.17286 0.83675 1.000 0.0485(16) . G
C15D C Uiso 0.69865 0.11026 0.86957 1.000 0.0485(16) . G
C16D C Uiso 0.52429 0.06922 0.85792 1.000 0.0485(16) . G
H1A H Uiso 0.60680 0.64493 0.44226 1.000 0.0760 . G
H2A H Uiso 0.43898 0.58793 0.45000 1.000 0.0760 . G
H3A H Uiso 0.06188 0.63181 0.36577 1.000 0.0760 . G
H4A H Uiso -0.12486 0.67118 0.28161 1.000 0.0760 . G
H5A H Uiso -0.16374 0.68578 0.17518 1.000 0.0760 . G
H6A H Uiso 0.13408 0.64205 0.10667 1.000 0.0760 . G
H7A H Uiso 0.46939 0.58381 0.14523 1.000 0.0760 . G
H8A H Uiso 0.72218 0.56301 0.23189 1.000 0.0760 . G
H9A H Uiso 0.75244 0.48733 0.31522 1.000 0.0760 . G
H10A H Uiso 0.54855 0.38952 0.35831 1.000 0.0760 . G
H11A H Uiso 0.25205 0.35054 0.42568 1.000 0.0760 . G
H12A H Uiso -0.05994 0.42732 0.45771 1.000 0.0760 . G
H13A H Uiso -0.07359 0.54251 0.42235 1.000 0.0760 . G
H1B H Uiso 0.31759 0.24434 0.64161 1.000 0.0760 . G
H2B H Uiso 0.14042 0.19033 0.65471 1.000 0.0760 . G
H3B H Uiso -0.22316 0.22703 0.56397 1.000 0.0760 . G
H4B H Uiso -0.39157 0.25529 0.47472 1.000 0.0760 . G
H5B H Uiso -0.41354 0.25359 0.36802 1.000 0.0760 . G
H6B H Uiso -0.11430 0.19565 0.30886 1.000 0.0760 . G
H7B H Uiso 0.20544 0.13961 0.35701 1.000 0.0760 . G
H8B H Uiso 0.44296 0.12938 0.44694 1.000 0.0760 . G
H9B H Uiso 0.44831 0.06685 0.53860 1.000 0.0760 . G
H10B H Uiso 0.22077 -0.02107 0.59149 1.000 0.0760 . G
H11B H Uiso -0.09202 -0.04555 0.66000 1.000 0.0760 . G
H12B H Uiso -0.39454 0.03971 0.67904 1.000 0.0760 . G
H13B H Uiso -0.38252 0.14883 0.62964 1.000 0.0760 . G
H1C H Uiso 0.47026 0.48935 0.93322 1.000 0.0760 . G
H2C H Uiso 0.28514 0.50994 0.88565 1.000 0.0760 . G
H3C H Uiso -0.13272 0.56929 0.95858 1.000 0.0760 . G
H4C H Uiso -0.35552 0.63380 1.02438 1.000 0.0760 . G
H5C H Uiso -0.45490 0.73315 1.07664 1.000 0.0760 . G
H6C H Uiso -0.21846 0.82397 1.06322 1.000 0.0760 . G
H7C H Uiso 0.11640 0.81476 0.99740 1.000 0.0760 . G
H8C H Uiso 0.41486 0.73884 0.94490 1.000 0.0760 . G
H9C H Uiso 0.46490 0.69249 0.85190 1.000 0.0760 . G
H10C H Uiso 0.24581 0.69663 0.75896 1.000 0.0760 . G
H11C H Uiso -0.02552 0.64742 0.70572 1.000 0.0760 . G
H12C H Uiso -0.28483 0.57692 0.75980 1.000 0.0760 . G
H13C H Uiso -0.27121 0.55594 0.86662 1.000 0.0760 . G
H1D H Uiso 0.07465 -0.06128 0.98277 1.000 0.0760 . G
H2D H Uiso 0.25671 -0.09895 0.93879 1.000 0.0760 . G
H3D H Uiso 0.64077 -0.00328 0.92328 1.000 0.0760 . G
H4D H Uiso 0.83857 -0.09985 0.89267 1.000 0.0760 . G
H5D H Uiso 0.90935 -0.19154 0.82932 1.000 0.0760 . G
H6D H Uiso 0.65900 -0.20373 0.75131 1.000 0.0760 . G
H7D H Uiso 0.33899 -0.12387 0.73716 1.000 0.0760 . G
H8D H Uiso 0.06404 -0.03571 0.78231 1.000 0.0760 . G
H9D H Uiso 0.04303 0.07947 0.78735 1.000 0.0760 . G
H10D H Uiso 0.28389 0.17124 0.74952 1.000 0.0760 . G
H11D H Uiso 0.57740 0.23850 0.76937 1.000 0.0760 . G
H12D H Uiso 0.83792 0.20029 0.84511 1.000 0.0760 . G
H13D H Uiso 0.80338 0.09527 0.90059 1.000 0.0760 . G

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1A C2A 1.2268
O1B C2B 1.2269
O1C C2C 1.2270
O1D C2D 1.2270
N1A C2A 1.3949
N1A H1A 0.9000
N1A H2A 0.9000
N1B C2B 1.3949
N1B H2B 0.9000
N1B H1B 0.9000
N1C C2C 1.3949
N1C H2C 0.9000
N1C H1C 0.9000
N1D C2D 1.3949
N1D H2D 0.9000
N1D H1D 0.9000
C1A C16A 1.5035
C1A C2A 1.5300
C1A C3A 1.5040
C3A C4A 1.3996
C3A C8A 1.4019
C4A C5A 1.3867
C5A C6A 1.3931
C6A C7A 1.3859
C7A C8A 1.4015
C8A C9A 1.4583
C9A C10A 1.3387
C10A C11A 1.4580
C11A C12A 1.4024
C11A C16A 1.4001
C12A C13A 1.3857
C13A C14A 1.3924
C14A C15A 1.3871
C15A C16A 1.3999
C1A H3A 0.9900
C4A H4A 0.9500
C5A H5A 0.9500
C6A H6A 0.9500
C7A H7A 0.9500
C9A H8A 0.9500
C10A H9A 0.9500
C12A H10A 0.9500
C13A H11A 0.9500
C14A H12A 0.9500
C15A H13A 0.9500
C1B C2B 1.5300
C1B C16B 1.5033
C1B C3B 1.5041
C3B C4B 1.3997
C3B C8B 1.4017
C4B C5B 1.3866
C5B C6B 1.3931
C6B C7B 1.3859
C7B C8B 1.4015
C8B C9B 1.4583
C9B C10B 1.3387
C10B C11B 1.4580
C11B C16B 1.4002
C11B C12B 1.4026
C12B C13B 1.3856
C13B C14B 1.3925
C14B C15B 1.3872
C15B C16B 1.3998
C1B H3B 0.9900
C4B H4B 0.9500
C5B H5B 0.9500
C6B H6B 0.9500
C7B H7B 0.9500
C9B H8B 0.9500
C10B H9B 0.9500
C12B H10B 0.9500
C13B H11B 0.9500
C14B H12B 0.9500
C15B H13B 0.9500
C1C C16C 1.5033
C1C C3C 1.5041
C1C C2C 1.5300
C3C C4C 1.3995
C3C C8C 1.4018
C4C C5C 1.3868
C5C C6C 1.3930
C6C C7C 1.3858
C7C C8C 1.4015
C8C C9C 1.4583
C9C C10C 1.3387
C10C C11C 1.4578
C11C C12C 1.4027
C11C C16C 1.4002
C12C C13C 1.3856
C13C C14C 1.3924
C14C C15C 1.3871
C15C C16C 1.3998
C1C H3C 0.9900
C4C H4C 0.9500
C5C H5C 0.9500
C6C H6C 0.9500
C7C H7C 0.9500
C9C H8C 0.9500
C10C H9C 0.9500
C12C H10C 0.9500
C13C H11C 0.9500
C14C H12C 0.9500
C15C H13C 0.9500
C1D C16D 1.5034
C1D C2D 1.5299
C1D C3D 1.5040
C3D C8D 1.4018
C3D C4D 1.3997
C4D C5D 1.3866
C5D C6D 1.3930
C6D C7D 1.3859
C7D C8D 1.4015
C8D C9D 1.4583
C9D C10D 1.3385
C10D C11D 1.4580
C11D C16D 1.4003
C11D C12D 1.4025
C12D C13D 1.3855
C13D C14D 1.3925
C14D C15D 1.3870
C15D C16D 1.3998
C1D H3D 0.9900
C4D H4D 0.9500
C5D H5D 0.9500
C6D H6D 0.9500
C7D H7D 0.9500
C9D H8D 0.9500
C10D H9D 0.9500
C12D H10D 0.9500
C13D H11D 0.9500
C14D H12D 0.9500
C15D H13D 0.9500

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
H1A N1A H2A 118.00
C2A N1A H2A 121.00
C2A N1A H1A 121.00
C2B N1B H2B 121.00
C2B N1B H1B 121.00
H1B N1B H2B 118.00
C2C N1C H1C 121.00
C2C N1C H2C 121.00
H1C N1C H2C 118.00
H1D N1D H2D 118.00
C2D N1D H2D 121.00
C2D N1D H1D 121.00
C2A C1A C16A 112.20
C3A C1A C16A 110.05
C2A C1A C3A 114.55
O1A C2A C1A 124.22
N1A C2A C1A 119.55
O1A C2A N1A 116.08
C1A C3A C8A 122.82
C4A C3A C8A 119.18
C1A C3A C4A 117.99
C3A C4A C5A 120.90
C4A C5A C6A 119.87
C5A C6A C7A 119.86
C6A C7A C8A 120.72
C3A C8A C7A 119.46
C3A C8A C9A 123.00
C7A C8A C9A 117.54
C8A C9A C10A 125.92
C9A C10A C11A 125.94
C10A C11A C12A 117.40
C12A C11A C16A 119.43
C10A C11A C16A 123.17
C11A C12A C13A 120.67
C12A C13A C14A 119.91
C13A C14A C15A 119.89
C14A C15A C16A 120.77
C1A C16A C11A 122.64
C1A C16A C15A 118.03
C11A C16A C15A 119.32
C16A C1A H3A 108.00
C2A C1A H3A 104.00
C3A C1A H3A 108.00
C5A C4A H4A 120.00
C3A C4A H4A 120.00
C6A C5A H5A 120.00
C4A C5A H5A 120.00
C5A C6A H6A 120.00
C7A C6A H6A 120.00
C6A C7A H7A 120.00
C8A C7A H7A 119.00
C10A C9A H8A 119.00
C8A C9A H8A 115.00
C9A C10A H9A 119.00
C11A C10A H9A 115.00
C11A C12A H10A 119.00
C13A C12A H10A 120.00
C14A C13A H11A 120.00
C12A C13A H11A 120.00
C15A C14A H12A 120.00
C13A C14A H12A 120.00
C16A C15A H13A 120.00
C14A C15A H13A 120.00
C3B C1B C16B 110.05
C2B C1B C16B 112.20
C2B C1B C3B 114.55
O1B C2B C1B 124.22
O1B C2B N1B 116.09
N1B C2B C1B 119.55
C4B C3B C8B 119.19
C1B C3B C8B 122.82
C1B C3B C4B 117.98
C3B C4B C5B 120.90
C4B C5B C6B 119.87
C5B C6B C7B 119.86
C6B C7B C8B 120.72
C3B C8B C7B 119.47
C3B C8B C9B 123.00
C7B C8B C9B 117.53
C8B C9B C10B 125.92
C9B C10B C11B 125.94
C10B C11B C12B 117.40
C10B C11B C16B 123.17
C12B C11B C16B 119.42
C11B C12B C13B 120.67
C12B C13B C14B 119.92
C13B C14B C15B 119.89
C14B C15B C16B 120.78
C1B C16B C15B 118.04
C11B C16B C15B 119.32
C1B C16B C11B 122.64
C16B C1B H3B 108.00
C3B C1B H3B 108.00
C2B C1B H3B 104.00
C5B C4B H4B 120.00
C3B C4B H4B 120.00
C6B C5B H5B 120.00
C4B C5B H5B 120.00
C5B C6B H6B 120.00
C7B C6B H6B 120.00
C8B C7B H7B 119.00
C6B C7B H7B 120.00
C10B C9B H8B 119.00
C8B C9B H8B 115.00
C9B C10B H9B 119.00
C11B C10B H9B 115.00
C11B C12B H10B 119.00
C13B C12B H10B 120.00
C12B C13B H11B 120.00
C14B C13B H11B 120.00
C13B C14B H12B 120.00
C15B C14B H12B 120.00
C16B C15B H13B 120.00
C14B C15B H13B 120.00
C3C C1C C16C 110.06
C2C C1C C3C 114.55
C2C C1C C16C 112.19
O1C C2C N1C 116.08
O1C C2C C1C 124.22
N1C C2C C1C 119.56
C4C C3C C8C 119.19
C1C C3C C8C 122.82
C1C C3C C4C 117.99
C3C C4C C5C 120.90
C4C C5C C6C 119.87
C5C C6C C7C 119.87
C6C C7C C8C 120.72
C7C C8C C9C 117.54
C3C C8C C9C 122.99
C3C C8C C7C 119.46
C8C C9C C10C 125.93
C9C C10C C11C 125.93
C10C C11C C12C 117.40
C10C C11C C16C 123.18
C12C C11C C16C 119.41
C11C C12C C13C 120.68
C12C C13C C14C 119.91
C13C C14C C15C 119.89
C14C C15C C16C 120.78
C1C C16C C15C 118.05
C11C C16C C15C 119.32
C1C C16C C11C 122.63
C3C C1C H3C 108.00
C2C C1C H3C 104.00
C16C C1C H3C 108.00
C3C C4C H4C 120.00
C5C C4C H4C 120.00
C6C C5C H5C 120.00
C4C C5C H5C 120.00
C5C C6C H6C 120.00
C7C C6C H6C 120.00
C6C C7C H7C 120.00
C8C C7C H7C 119.00
C8C C9C H8C 115.00
C10C C9C H8C 119.00
C9C C10C H9C 119.00
C11C C10C H9C 115.00
C13C C12C H10C 120.00
C11C C12C H10C 119.00
C12C C13C H11C 120.00
C14C C13C H11C 120.00
C13C C14C H12C 120.00
C15C C14C H12C 120.00
C14C C15C H13C 120.00
C16C C15C H13C 120.00
C3D C1D C16D 110.05
C2D C1D C16D 112.20
C2D C1D C3D 114.55
O1D C2D N1D 116.07
O1D C2D C1D 124.22
N1D C2D C1D 119.56
C4D C3D C8D 119.19
C1D C3D C4D 117.98
C1D C3D C8D 122.82
C3D C4D C5D 120.89
C4D C5D C6D 119.87
C5D C6D C7D 119.86
C6D C7D C8D 120.72
C7D C8D C9D 117.55
C3D C8D C7D 119.46
C3D C8D C9D 122.99
C8D C9D C10D 125.93
C9D C10D C11D 125.93
C10D C11D C12D 117.41
C10D C11D C16D 123.17
C12D C11D C16D 119.42
C11D C12D C13D 120.67
C12D C13D C14D 119.91
C13D C14D C15D 119.89
C14D C15D C16D 120.78
C1D C16D C11D 122.64
C1D C16D C15D 118.04
C11D C16D C15D 119.32
C2D C1D H3D 104.00
C3D C1D H3D 108.00
C16D C1D H3D 108.00
C3D C4D H4D 120.00
C5D C4D H4D 120.00
C4D C5D H5D 120.00
C6D C5D H5D 120.00
C5D C6D H6D 120.00
C7D C6D H6D 120.00
C6D C7D H7D 120.00
C8D C7D H7D 119.00
C8D C9D H8D 115.00
C10D C9D H8D 119.00
C9D C10D H9D 119.00
C11D C10D H9D 115.00
C11D C12D H10D 119.00
C13D C12D H10D 120.00
C12D C13D H11D 120.00
C14D C13D H11D 120.00
C13D C14D H12D 120.00
C15D C14D H12D 120.00
C14D C15D H13D 120.00
C16D C15D H13D 120.00

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
C2A C1A C3A C8A 66.83
C2A C1A C3A C4A -114.28
C16A C1A C2A O1A 150.25
C16A C1A C3A C4A 118.21
C16A C1A C2A N1A -25.23
C16A C1A C3A C8A -60.69
C3A C1A C16A C11A 61.23
C3A C1A C16A C15A -118.89
C3A C1A C2A N1A -151.63
C2A C1A C16A C15A 112.31
C3A C1A C2A O1A 23.85
C2A C1A C16A C11A -67.57
C1A C3A C8A C9A -0.82
C4A C3A C8A C7A 0.77
C4A C3A C8A C9A -179.71
C1A C3A C4A C5A -179.30
C8A C3A C4A C5A -0.36
C1A C3A C8A C7A 179.65
C3A C4A C5A C6A -0.03
C4A C5A C6A C7A 0.02
C5A C6A C7A C8A 0.39
C6A C7A C8A C9A 179.66
C6A C7A C8A C3A -0.79
C3A C8A C9A C10A 38.81
C7A C8A C9A C10A -141.66
C8A C9A C10A C11A 0.17
C9A C10A C11A C16A -38.65
C9A C10A C11A C12A 141.91
C10A C11A C12A C13A -179.70
C12A C11A C16A C1A 179.35
C10A C11A C16A C15A -179.97
C16A C11A C12A C13A 0.84
C12A C11A C16A C15A -0.53
C10A C11A C16A C1A -0.07
C11A C12A C13A C14A -0.59
C12A C13A C14A C15A 0.04
C13A C14A C15A C16A 0.27
C14A C15A C16A C1A -179.91
C14A C15A C16A C11A 0.00
C16B C1B C2B O1B 151.57
C16B C1B C2B N1B -23.91
C2B C1B C3B C4B -114.27
C2B C1B C3B C8B 66.82
C16B C1B C3B C4B 118.21
C2B C1B C16B C11B -67.58
C2B C1B C16B C15B 112.32
C3B C1B C2B N1B -150.32
C3B C1B C16B C15B -118.88
C16B C1B C3B C8B -60.69
C3B C1B C16B C11B 61.23
C3B C1B C2B O1B 25.16
C4B C3B C8B C9B -179.71
C4B C3B C8B C7B 0.75
C1B C3B C8B C9B -0.82
C1B C3B C4B C5B -179.29
C8B C3B C4B C5B -0.35
C1B C3B C8B C7B 179.64
C3B C4B C5B C6B -0.05
C4B C5B C6B C7B 0.04
C5B C6B C7B C8B 0.37
C6B C7B C8B C9B 179.66
C6B C7B C8B C3B -0.77
C3B C8B C9B C10B 38.81
C7B C8B C9B C10B -141.64
C8B C9B C10B C11B 0.16
C9B C10B C11B C12B 141.92
C9B C10B C11B C16B -38.64
C10B C11B C12B C13B -179.69
C12B C11B C16B C15B -0.55
C10B C11B C16B C1B -0.07
C10B C11B C16B C15B -179.97
C12B C11B C16B C1B 179.35
C16B C11B C12B C13B 0.85
C11B C12B C13B C14B -0.60
C12B C13B C14B C15B 0.05
C13B C14B C15B C16B 0.24
C14B C15B C16B C1B -179.89
C14B C15B C16B C11B 0.00
C3C C1C C2C N1C -149.74
C16C C1C C2C O1C 152.17
C16C C1C C2C N1C -23.32
C2C C1C C3C C4C -114.28
C2C C1C C3C C8C 66.83
C16C C1C C3C C4C 118.21
C16C C1C C3C C8C -60.68
C3C C1C C2C O1C 25.76
C3C C1C C16C C11C 61.22
C2C C1C C16C C11C -67.59
C2C C1C C16C C15C 112.32
C3C C1C C16C C15C -118.87
C4C C3C C8C C7C 0.77
C8C C3C C4C C5C -0.36
C1C C3C C8C C7C 179.65
C1C C3C C8C C9C -0.83
C4C C3C C8C C9C -179.71
C1C C3C C4C C5C -179.29
C3C C4C C5C C6C -0.05
C4C C5C C6C C7C 0.04
C5C C6C C7C C8C 0.39
C6C C7C C8C C9C 179.66
C6C C7C C8C C3C -0.80
C3C C8C C9C C10C 38.83
C7C C8C C9C C10C -141.65
C8C C9C C10C C11C 0.15
C9C C10C C11C C12C 141.93
C9C C10C C11C C16C -38.66
C10C C11C C16C C15C -179.96
C10C C11C C12C C13C -179.70
C16C C11C C12C C13C 0.86
C12C C11C C16C C1C 179.35
C12C C11C C16C C15C -0.56
C10C C11C C16C C1C -0.06
C11C C12C C13C C14C -0.60
C12C C13C C14C C15C 0.05
C13C C14C C15C C16C 0.25
C14C C15C C16C C1C -179.90
C14C C15C C16C C11C 0.02
C3D C1D C2D O1D -158.45
C2D C1D C3D C8D 66.82
C16D C1D C3D C4D 118.22
C16D C1D C3D C8D -60.69
C3D C1D C2D N1D 26.07
C16D C1D C2D O1D -32.05
C16D C1D C2D N1D 152.48
C2D C1D C3D C4D -114.27
C3D C1D C16D C15D -118.87
C3D C1D C16D C11D 61.22
C2D C1D C16D C11D -67.59
C2D C1D C16D C15D 112.32
C8D C3D C4D C5D -0.34
C1D C3D C8D C7D 179.66
C1D C3D C8D C9D -0.81
C4D C3D C8D C7D 0.75
C1D C3D C4D C5D -179.30
C4D C3D C8D C9D -179.71
C3D C4D C5D C6D -0.06
C4D C5D C6D C7D 0.04
C5D C6D C7D C8D 0.38
C6D C7D C8D C9D 179.66
C6D C7D C8D C3D -0.78
C3D C8D C9D C10D 38.82
C7D C8D C9D C10D -141.64
C8D C9D C10D C11D 0.15
C9D C10D C11D C16D -38.64
C9D C10D C11D C12D 141.93
C16D C11D C12D C13D 0.86
C10D C11D C16D C1D -0.07
C10D C11D C16D C15D -179.97
C10D C11D C12D C13D -179.69
C12D C11D C16D C1D 179.35
C12D C11D C16D C15D -0.56
C11D C12D C13D C14D -0.60
C12D C13D C14D C15D 0.05
C13D C14D C15D C16D 0.25
C14D C15D C16D C1D -179.90
C14D C15D C16D C11D 0.00

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
#
#D H A D - H H...A D...A D-H...A symm(A)
#
N1A H1A O1B 0.9000 1.9000 2.7702 162.00 2_666
N1B H1B O1A 0.9000 1.7600 2.6446 168.00 2_666
N1C H1C O1C 0.9000 1.9200 2.7852 160.00 2_667
N1D H1D O1D 0.9000 1.9200 2.8111 173.00 2_557

_exptl_special_details           
;
Cytenamide is an analogue of carbamazepine, a dibenzazepine drug used to
control seizures. This form II structure is a lab X-ray powder structure
determination.
;

_refine_special_details          
;
The diffraction pattern indexed to a triclinic unit cell with dimensions
sufficiently similar to triclinic carbamazepine form I to suggest that the
former is essentially isostructural with the latter. This was confirmed by a
rigid-body Rietveld refinement of cytenamide form II (Topas), starting from a
structure generated using simulated annealing (DASH). The final refinement
included a total of 72 parameters (22 profile, 6 cell, 1 scale, 1 isotropic
temperature factor, 14 preferred orientation, 4 torsion angles, 12 position, 12
rotation), yielding Rwp = 4.05. The maximum e.s.u. for the rigid-body
positional and orientational parameters was small, at 0.0011 and 0.53 degrees,
respectively. The resulting structure was further inspected by allowing the
fractional coordinates to refine freely (416 parameters, Rwp = 1.69). As
expected, the improved Rwp came at the expense of some chemical sense (e.g. H-
atoms moving to nonsensical positions), but, otherwise, the geometry of each of
the four independent molecules was sufficiently well preserved to confirm the
correctness of the rigid-body refined crystal structure reported here.
;

# Attachment 'CYT_FORM_I_CSD_Dec07_v4.cif'

#==============================================================================
data_cytenamide_form_I_trigonal_SX_structure
_database_code_depnum_ccdc_archive 'CCDC 672213'
#==============================================================================

_audit_creation_date             07-09-27
_audit_creation_method           CRYSTALS_ver_12.85
_oxford_structure_analysis_title '2007src1155 in R-3'

_chemical_name_systematic        
;
5H-Dibenzo[a,d]cycloheptene-5-carboxamide
;
_chemical_name_common            'Cytenamide form I'

_publ_section_exptl_refinement   
;
Data were merged with SORTAV (Blessing, 1997). Full-matrix least-squares
structure refinement against <i>F</i>^2^ was performed using the program
CRYSTALS. All non-H atoms were refined anisotropically. H-atoms were found on a
difference Fourier map and were initially refined with soft restraints on the
bond lengths and angles to regularize their geometry and <i>U</i>~iso~(H) (in
the range 1.2--1.5 times <i>U</i>~eq~ of the parent atom), after which the
positions were refined with riding constraints.
Three peaks of conspicuous electron density near the high-symmetry site were
located on a difference Fourier map. Based on their heights and separations,
these were assigned to O- and C-atoms of an ethanol moiety. However, refinement
of their positions failed to yield a satisfactory model. Given that the solvent
of crystallization (industrial methylated spirits) has >1 component, the
possibility that methanol and/or water could also be present in the cavities
cannot be excluded, further complicating the modelling of disorder.
Accordingly, an unsolvated model was refined, using PLATON/SQUEEZE to correct
for the contribution of the disordered solvent to the diffraction pattern. A
total of 6 e^-^ was found in three voids of ca. 128 A^3^ each. These were
located at (0,0,-0.012), (1/3,2/3,0.393) and (2/3,1/3,0.060). The electron count
is not consistent with a reasonable solvent stoichiometry, but the void volume
can accomodate a small molecule such as methanol, ethanol or water. It is well
known that the number of recovered electrons in the solvent area is strongly
dependent on the quality of the low-angle reflections. Though a complete, merged
data set was fed into the program, the overall quality of the data is not ideal
and the ratio of observed/unique reflections is only ca. 50%. The electron count
was not taken into account for calculation of density, F(000) and related
crystal data.
;

_cell_length_a                   33.9078(10)
_cell_length_b                   33.9078(10)
_cell_length_c                   5.6754(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     5651.0(3)

_symmetry_cell_setting           Trigonal
_symmetry_space_group_name_H-M   'R -3 '
_symmetry_space_group_name_Hall  '-R 3'
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -y,x-y,z
3 -x+y,-x,z
4 -x,-y,-z
5 y,-x+y,-z
6 x-y,x,-z
7 1/3+x,2/3+y,2/3+z
8 1/3-y,2/3+x-y,2/3+z
9 1/3-x+y,2/3-x,2/3+z
10 1/3-x,2/3-y,2/3-z
11 1/3+y,2/3-x+y,2/3-z
12 1/3+x-y,2/3+x,2/3-z
13 2/3+x,1/3+y,1/3+z
14 2/3-y,1/3+x-y,1/3+z
15 2/3-x+y,1/3-x,1/3+z
16 2/3-x,1/3-y,1/3-z
17 2/3+y,1/3-x+y,1/3-z
18 2/3+x-y,1/3+x,1/3-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            18

_chemical_formula_sum            'C16 H13 N1 O1'
_chemical_formula_moiety         'C16 H13 N1 O1'
_chemical_formula_weight         235.27
_chemical_melting_point          ?
_chemical_compound_source        
;
5H-Dibenzo[a,d]cyclohepten-5-one (Sigma-Aldrich) was converted by sodium
borohydride reduction in methanol into 5H-dibenzo[a,d]cycloheptenyl-5-ol. This
alcohol was converted by literature methods sequentially into the corresponding
5-chloro compound, the 5-cyano compound and the corresponding amide, 5H-
dibenzo[a,d]cycloheptene-5-carboxamide (cytenamide).
;

_cell_measurement_reflns_used    26511
_cell_measurement_theta_min      3
_cell_measurement_theta_max      28
_cell_measurement_temperature    120

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.005
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_max          0.30
_exptl_crystal_preparation       
;
Recrystallisation of cytenamide from industrial methylated spirits produced a
sample from which a fine needle was taken for single-crystal analysis and
designated form I.
;

_exptl_crystal_density_diffrn    1.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             2232
_exptl_absorpt_coefficient_mu    0.078

# Sheldrick geometric approximatio 1.00 1.00
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_absorpt_correction_T_min  0.611
_exptl_absorpt_correction_T_max  1.000
_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 Roper CCD camera on \k-goniostat
;
_diffrn_measurement_method       '\f & \w scans'
_diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm'

_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    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_reflns_reduction_process 
;
Scaled and merged with SORTAV
R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
#_diffrn_reflns_limit_h_max 43
#_diffrn_reflns_limit_h_min -37
#_diffrn_reflns_limit_k_max 43
#_diffrn_reflns_limit_k_min -43
#_diffrn_reflns_limit_l_max 6
#_diffrn_reflns_limit_l_min -7
_diffrn_reflns_number            13159
_reflns_number_total             2882
_diffrn_reflns_av_R_equivalents  0.1061
# Number of reflections with Friedels Law is 2882
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 2883

_diffrn_reflns_theta_min         3.179
_diffrn_reflns_theta_max         27.492
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        27.492
_diffrn_measured_fraction_theta_full 0.997

_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       7
_reflns_limit_h_min              -43
_reflns_limit_h_max              20
_reflns_limit_k_min              0
_reflns_limit_k_max              43
_reflns_limit_l_min              0
_reflns_limit_l_max              7

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.55
_refine_diff_density_max         0.53

# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold

# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns         2882
_refine_ls_number_restraints     0
_refine_ls_number_parameters     163
_oxford_refine_ls_R_factor_ref   0.1461
_refine_ls_wR_factor_ref         0.2150
_refine_ls_goodness_of_fit_ref   0.9575
_refine_ls_shift/su_max          0.000271

# The values computed from all data
_oxford_reflns_number_all        2882
_refine_ls_R_factor_all          0.1461
_refine_ls_wR_factor_all         0.2150

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                1381
_refine_ls_R_factor_gt           0.0710
_refine_ls_wR_factor_gt          0.1685

# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.10P)^2^ + 9.53P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;

_publ_section_references         
;
User-defined data collection reference

User defined data reduction

User defined cell refinement

Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M. C.,
Polidori, G. & Camalli, M. (1994). <i>J. Appl. Cryst.</i> <b>27</b>, 435--?.

Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J.
(2003). <i>J. Appl. Cryst.</i> <b>36</b>, 1487--?.

Blessing, R. H. (1997). <i>J. Appl. Cryst.</i> <b>30</b>, 421--?.

Duisenberg, A. J. M. (1992). <i>J. Appl. Cryst.</i> <b>25</b>, 92--96.

Duisenberg, A. J. M, Hooft, R. W. W, Schreurs, A. M. M. & Kroon (2000). <i>J.
Appl. Cryst.</i> <b>33</b>, 893--898.

Hooft, R. W. W. (1998). <i>COLLECT</i> data collection software, Nonius B.V.

Otwinowski, Z. & Minor, W. (1997). Macromolecular Crystallography, Pt A., 276,
307-326.

Sheldrick, G. M. (2007). <i>SADABS</i>. Version 2007/2. Bruker AXS Inc.,
Madison, Wisconsin, USA.
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atomsattached to an atom.

# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint

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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
O1 O 0.54274(7) 0.53371(7) 0.2885(4) 0.0394(8) 1.0000 Uani . . . . . . .
C2 C 0.59351(10) 0.44483(11) 0.1568(5) 0.0353(10) 1.0000 Uani . . . . . . .
C3 C 0.61319(11) 0.56643(11) -0.2241(5) 0.0355(10) 1.0000 Uani . . . . . . .
C4 C 0.53715(10) 0.49713(11) 0.2174(5) 0.0325(10) 1.0000 Uani . . . . . . .
N5 N 0.50660(9) 0.45758(9) 0.3131(5) 0.0404(9) 1.0000 Uani . . . . . . .
C6 C 0.56312(10) 0.49457(10) -0.0001(5) 0.0309(9) 1.0000 Uani . . . . . . .
C7 C 0.56746(10) 0.45246(11) -0.0095(5) 0.0341(9) 1.0000 Uani . . . . . . .
C8 C 0.62056(11) 0.47807(12) 0.3381(6) 0.0376(11) 1.0000 Uani . . . . . . .
C9 C 0.64193(10) 0.52361(11) 0.3271(5) 0.0332(10) 1.0000 Uani . . . . . . .
C10 C 0.68766(11) 0.62230(11) -0.0917(6) 0.0394(10) 1.0000 Uani . . . . . . .
C11 C 0.68232(11) 0.59468(11) 0.0999(6) 0.0379(10) 1.0000 Uani . . . . . . .
C12 C 0.60782(10) 0.53845(10) -0.0340(5) 0.0307(9) 1.0000 Uani . . . . . . .
C13 C 0.64314(10) 0.55200(10) 0.1304(5) 0.0320(9) 1.0000 Uani . . . . . . .
C14 C 0.54360(12) 0.41939(11) -0.1797(6) 0.0415(11) 1.0000 Uani . . . . . . .
C15 C 0.65271(11) 0.60772(11) -0.2552(6) 0.0378(10) 1.0000 Uani . . . . . . .
C16 C 0.57069(13) 0.37185(12) -0.0251(7) 0.0484(11) 1.0000 Uani . . . . . . .
C17 C 0.59443(12) 0.40396(12) 0.1464(6) 0.0448(11) 1.0000 Uani . . . . . . .
C18 C 0.54508(13) 0.37933(12) -0.1898(6) 0.0489(12) 1.0000 Uani . . . . . . .
H31 H 0.5899 0.5570 -0.3380 0.0428 1.0000 Uiso R . . . . . .
H61 H 0.5456 0.4931 -0.1398 0.0361 1.0000 Uiso R . . . . . .
H81 H 0.6245 0.4661 0.4811 0.0463 1.0000 Uiso R . . . . . .
H91 H 0.6582 0.5385 0.4683 0.0409 1.0000 Uiso R . . . . . .
H101 H 0.7146 0.6509 -0.1146 0.0478 1.0000 Uiso R . . . . . .
H111 H 0.7054 0.6049 0.2157 0.0420 1.0000 Uiso R . . . . . .
H141 H 0.5248 0.4238 -0.2899 0.0446 1.0000 Uiso R . . . . . .
H151 H 0.6564 0.6258 -0.3916 0.0473 1.0000 Uiso R . . . . . .
H161 H 0.5722 0.3448 -0.0271 0.0567 1.0000 Uiso R . . . . . .
H171 H 0.6116 0.3992 0.2646 0.0539 1.0000 Uiso R . . . . . .
H181 H 0.5295 0.3579 -0.3103 0.0565 1.0000 Uiso R . . . . . .
H51 H 0.4933 0.4585 0.4461 0.0475 1.0000 Uiso R . . . . . .
H52 H 0.5018 0.4330 0.2393 0.0472 1.0000 Uiso 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 0.0375(13) 0.0349(13) 0.0428(13) -0.0011(10) 0.0080(10) 0.0158(10)
C2 0.0337(17) 0.0347(17) 0.0350(17) 0.0043(13) 0.0089(14) 0.0153(14)
C3 0.0384(18) 0.0378(18) 0.0307(16) -0.0029(13) -0.0008(13) 0.0193(15)
C4 0.0230(15) 0.0354(18) 0.0358(17) -0.0004(14) -0.0052(13) 0.0121(13)
N5 0.0384(16) 0.0319(15) 0.0449(16) -0.0003(12) 0.0117(12) 0.0130(13)
C6 0.0268(15) 0.0338(17) 0.0281(15) -0.0025(12) -0.0032(12) 0.0122(13)
C7 0.0297(16) 0.0337(17) 0.0330(16) 0.0008(13) 0.0048(13) 0.0115(14)
C8 0.0369(18) 0.044(2) 0.0356(17) 0.0011(15) 0.0018(14) 0.0230(16)
C9 0.0320(16) 0.0407(19) 0.0279(16) -0.0050(13) -0.0039(13) 0.0189(15)
C10 0.0322(17) 0.0322(17) 0.052(2) -0.0024(15) 0.0084(15) 0.0147(14)
C11 0.0270(16) 0.0363(18) 0.049(2) -0.0059(15) -0.0025(14) 0.0148(14)
C12 0.0297(16) 0.0327(16) 0.0300(16) -0.0053(13) 0.0008(12) 0.0159(14)
C13 0.0258(15) 0.0345(17) 0.0346(16) -0.0015(13) 0.0018(12) 0.0143(14)
C14 0.0386(19) 0.0387(19) 0.0381(18) -0.0031(15) 0.0010(15) 0.0125(15)
C15 0.0401(19) 0.0340(17) 0.0392(18) 0.0031(14) 0.0060(14) 0.0185(15)
C16 0.048(2) 0.0294(18) 0.064(2) 0.0010(17) 0.0114(18) 0.0166(17)
C17 0.043(2) 0.0393(19) 0.051(2) 0.0087(16) 0.0103(16) 0.0198(17)
C18 0.052(2) 0.036(2) 0.047(2) -0.0080(16) 0.0058(17) 0.0133(17)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          6.9(4)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.226(4)
N5 C4 1.333(4)
N5 H51 0.8900
N5 H52 0.8700
C2 C17 1.403(5)
C2 C7 1.402(5)
C2 C8 1.462(5)
C3 C15 1.382(5)
C3 C12 1.387(4)
C4 C6 1.544(5)
C6 C12 1.514(4)
C6 C7 1.508(5)
C7 C14 1.392(5)
C8 C9 1.340(5)
C9 C13 1.461(4)
C10 C15 1.387(5)
C10 C11 1.387(5)
C11 C13 1.402(5)
C12 C13 1.402(5)
C14 C18 1.385(5)
C16 C18 1.383(6)
C16 C17 1.380(5)
C3 H31 0.9400
C6 H61 0.9800
C8 H81 0.9500
C9 H91 0.9600
C10 H101 0.9500
C11 H111 0.9500
C14 H141 0.9600
C15 H151 0.9600
C16 H161 0.9400
C17 H171 0.9500
C18 H181 0.9400

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
H51 N5 H52 126.00
C4 N5 H52 116.00
C4 N5 H51 118.00
C8 C2 C17 118.4(3)
C7 C2 C17 118.8(3)
C7 C2 C8 122.8(3)
C12 C3 C15 121.4(3)
O1 C4 N5 122.2(3)
O1 C4 C6 121.1(3)
N5 C4 C6 116.6(3)
C7 C6 C12 113.7(3)
C4 C6 C7 114.2(2)
C4 C6 C12 111.4(2)
C2 C7 C6 121.3(3)
C2 C7 C14 119.0(3)
C6 C7 C14 119.7(3)
C2 C8 C9 128.7(3)
C8 C9 C13 128.0(3)
C11 C10 C15 119.0(3)
C10 C11 C13 122.0(3)
C3 C12 C6 119.7(3)
C3 C12 C13 119.7(3)
C6 C12 C13 120.6(3)
C9 C13 C11 118.3(3)
C9 C13 C12 123.7(3)
C11 C13 C12 118.0(3)
C7 C14 C18 121.8(4)
C3 C15 C10 119.9(3)
C17 C16 C18 120.3(4)
C2 C17 C16 121.1(4)
C14 C18 C16 119.1(3)
C12 C3 H31 120.00
C15 C3 H31 119.00
C4 C6 H61 108.00
C7 C6 H61 106.00
C12 C6 H61 103.00
C2 C8 H81 116.00
C9 C8 H81 115.00
C8 C9 H91 114.00
C13 C9 H91 118.00
C11 C10 H101 122.00
C15 C10 H101 119.00
C10 C11 H111 120.00
C13 C11 H111 118.00
C7 C14 H141 119.00
C18 C14 H141 119.00
C3 C15 H151 120.00
C10 C15 H151 120.00
C17 C16 H161 119.00
C18 C16 H161 121.00
C2 C17 H171 117.00
C16 C17 H171 122.00
C14 C18 H181 120.00
C16 C18 H181 121.00

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
C8 C2 C7 C6 -4.5(5)
C8 C2 C7 C14 178.4(3)
C7 C2 C17 C16 0.7(6)
C8 C2 C17 C16 -178.1(4)
C17 C2 C7 C14 -0.3(5)
C7 C2 C8 C9 -32.2(6)
C17 C2 C7 C6 176.8(3)
C17 C2 C8 C9 146.6(4)
C15 C3 C12 C6 177.1(3)
C15 C3 C12 C13 -0.3(5)
C12 C3 C15 C10 -1.3(6)
O1 C4 C6 C7 157.1(3)
O1 C4 C6 C12 26.5(5)
N5 C4 C6 C12 -157.5(3)
N5 C4 C6 C7 -27.0(4)
C4 C6 C7 C2 -66.5(4)
C4 C6 C7 C14 110.6(4)
C7 C6 C12 C3 118.5(3)
C7 C6 C12 C13 -64.2(4)
C12 C6 C7 C2 63.0(4)
C12 C6 C7 C14 -120.0(3)
C4 C6 C12 C3 -110.7(3)
C4 C6 C12 C13 66.6(4)
C6 C7 C14 C18 -177.5(3)
C2 C7 C14 C18 -0.3(6)
C2 C8 C9 C13 1.0(7)
C8 C9 C13 C11 -148.4(4)
C8 C9 C13 C12 29.7(6)
C15 C10 C11 C13 1.6(6)
C11 C10 C15 C3 0.6(6)
C10 C11 C13 C12 -3.0(5)
C10 C11 C13 C9 175.2(3)
C3 C12 C13 C9 -175.8(3)
C6 C12 C13 C11 -174.9(3)
C3 C12 C13 C11 2.4(5)
C6 C12 C13 C9 7.0(5)
C7 C14 C18 C16 0.5(6)
C17 C16 C18 C14 -0.1(6)
C18 C16 C17 C2 -0.5(6)

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
#
#D H A D - H H...A D...A D-H...A symm(A)
#
N5 H51 O1 0.8900 2.0400 2.914(4) 169.00 4_666

_exptl_special_details           
;
Cytenamide is an analogue of carbamazepine, a dibenzazepine drug used to
control seizures.
;

_refine_special_details          
;
The following are the results of the online checkcif procedure available
at http://checkcif.iucr.org/:

910_ALERT_3_C # Missing FCF Reflections Below TH(Min) ........ 3
911_ALERT_3_C # Missing FCF Refl. Between TH(Min) & STH/L=0.6 1
912_ALERT_3_C # Missing FCF Reflections Above STH/L=0.6 ...... 6

The data collection strategy was devised so as to collect a complete and
redundant dataset to 0.77 Ang. Resolution and completeness are given below.

#===============================================================================
Resolution & Completeness Statistics (Cumulative)
#===============================================================================
Theta sin(th)/Lambda Complete Expected Measured Missing
#-------------------------------------------------------------------------------
20.82 0.500 0.998 1314 1311 3
23.01 0.550 0.998 1746 1743 3
25.24 0.600 0.998 2273 2269 4
#----------------------------------------------------------- ACTA Min. Res. ----
27.49 0.650 0.997 2892 2882 10

ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
Tmin and Tmax reported: 0.611 1.000
Tmin(prime) and Tmax expected: 0.977 1.000
RR(prime) = 0.625
Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ........0.62

The single crystal used for the measurements was a fine needle
(0.3 x 0.01 x 0.005 mm3) and the absorption correction correspondingly highly
anisotropic.

PLAT601_ALERT_2_B Structure Contains Solvent Accessible VOIDS of 128.00 A**3

The voids are occupied by solvent that could not be modelled in a satisfactory
manner (see _publ_section_exptl_refinement). Below are the results of a
PLATON/SQUEEZE procedure:

#loop_
#_platon_squeeze_void_nr
#_platon_squeeze_void_average_x
#_platon_squeeze_void_average_y
#_platon_squeeze_void_average_z
#_platon_squeeze_void_volume
#_platon_squeeze_void_count_electrons
1 0.000 0.000 -0.012 128.1 1.8
2 0.333 0.667 0.393 126.4 1.9
3 0.667 0.333 0.060 126.4 1.9

PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ... 48 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang . 5

These alerts indicate that the data quality is not ideal, due to small volume
of the fine needle used for the measurements (0.3 x 0.01 x 0.005 mm3).

PLAT420_ALERT_2_C D-H Without Acceptor N5 - H52 ... ?

This is correct and consistent with isostructural carbamazepine form II.
;


