Two-dimensional similarity between forms I and II of cytenamide, a carbamazepine analogue
Florence, A. J.; Bedford, C. T.; Fabbiani, F. P. A.; Shankland, K.; Gelbrich, T.; Hursthouse, M. B.; Shankland, N.; Johnston, A.; Fernandes, P.; CrystEngComm 10 (2008) 811–; doi:10.1039/b719717a

data_7201925
_publ_section_title
;
 Two-dimensional similarity between forms I and II of cytenamide, a
 carbamazepine analogue
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              811
_journal_paper_doi               10.1039/b719717a
_journal_volume                  10
_journal_year                    2008
_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).
;
_chemical_formula_moiety         'C16 H13 N1 O1'
_chemical_formula_sum            'C16 H13 N O'
_chemical_formula_weight         235.27
_chemical_name_common            'Cytenamide form I'
_chemical_name_systematic
;
5H-Dibenzo[a,d]cycloheptene-5-carboxamide
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             07-09-27
_audit_creation_method           CRYSTALS_ver_12.85
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   33.9078(10)
_cell_length_b                   33.9078(10)
_cell_length_c                   5.6754(2)
_cell_measurement_reflns_used    26511
_cell_measurement_temperature    120
_cell_measurement_theta_max      28
_cell_measurement_theta_min      3
_cell_volume                     5651.0(3)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Bruker-Nonius Roper CCD camera on \k-goniostat
;
_diffrn_measurement_method       '\f & \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1061
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            13159
_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_theta_full        27.492
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         3.179
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.24
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2232
_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_size_max          0.30
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.53
_refine_diff_density_min         -0.55
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9575
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2882
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1461
_refine_ls_R_factor_gt           0.0710
_refine_ls_shift/su_max          0.000271
_refine_ls_structure_factor_coef Fsqd
_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
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2150
_refine_ls_wR_factor_gt          0.1685
_refine_ls_wR_factor_ref         0.2150
_reflns_limit_h_max              20
_reflns_limit_h_min              -43
_reflns_limit_k_max              43
_reflns_limit_k_min              0
_reflns_limit_l_max              7
_reflns_limit_l_min              0
_reflns_number_gt                1381
_reflns_number_total             2882
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.1461
_oxford_refine_ls_scale          6.9(4)
_oxford_reflns_number_all        2882
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '2007src1155 in R-3'
_cod_data_source_file            b719717a.txt
_cod_data_source_block           cytenamide_form_I_trigonal_SX_structure
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal' according
to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'R -3 '
_cod_original_formula_sum        'C16 H13 N1 O1'
_cod_database_code               7201925