#------------------------------------------------------------------------------
#$Date: 2016-03-04 13:40:13 +0200 (Fri, 04 Mar 2016) $
#$Revision: 177478 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/04/2020408.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2020408
loop_
_publ_author_name
'Buist, Amanda R.'
'Kennedy, Alan R.'
_publ_section_title
;
 Salt forms of the pharmaceutical amide dihydrocarbamazepine
;
_journal_coeditor_code           YF3097
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              155
_journal_page_last               160
_journal_paper_doi               10.1107/S2053229616001133
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C15 H15 N2 O +, Cl -, H2 O'
_chemical_formula_moiety         'C15 H15 N2 O +, Cl -, H2 O'
_chemical_formula_sum            'C15 H17 Cl N2 O2'
_chemical_formula_weight         292.76
_chemical_name_systematic
'(10,11-Dihydro-5H-dibenzo[b,f]azepin-5-yl)(hydroxy)methylidene]azanium chloride monohydrate'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.731(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.3048(3)
_cell_length_b                   24.4966(14)
_cell_length_c                   11.0163(6)
_cell_measurement_reflns_used    2171
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.8000
_cell_measurement_theta_min      3.1067
_cell_volume                     1421.70(14)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2014)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008) and ORTEP-3 for Windows (Farrugia,
2012)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.929
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur E'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0634
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7044
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         3.11
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.272
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.274
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3507
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0362P)²+0.1996P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0994
_reflns_number_gt                2477
_reflns_number_total             3507
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            yf3097sup1.cif
_cod_data_source_block           II
_cod_depositor_comments
'Adding full bibliography for 2020407--2020409.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2020408
_cod_database_fobs_code          2020408
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'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Cl Cl1 0.22098(8) 0.54240(2) 0.68704(4) 0.02364(13) Uani d . 1 1
O O1 0.3193(2) 0.35371(5) 0.42865(12) 0.0195(3) Uani d . 1 1
O O1W 0.2533(3) 0.40465(6) 0.23288(12) 0.0221(3) Uani d . 1 1
N N1 0.5160(3) 0.36537(6) 0.61893(13) 0.0153(3) Uani d . 1 1
N N2 0.2632(3) 0.43409(7) 0.52585(16) 0.0206(4) Uani d . 1 1
C C1 0.5617(3) 0.39448(7) 0.73387(16) 0.0153(4) Uani d . 1 1
C C2 0.4221(3) 0.37804(8) 0.82641(16) 0.0174(4) Uani d . 1 1
C C3 0.2334(3) 0.33258(8) 0.80044(17) 0.0197(4) Uani d . 1 1
H H3A 0.1249 0.3403 0.7230 0.024 Uiso calc R 1 1
H H3B 0.1226 0.3309 0.8667 0.024 Uiso calc R 1 1
C C4 0.3647(4) 0.27728(8) 0.79053(17) 0.0204(4) Uani d . 1 1
H H4A 0.4579 0.2688 0.8715 0.025 Uiso calc R 1 1
H H4B 0.2307 0.2492 0.7738 0.025 Uiso calc R 1 1
C C5 0.5485(3) 0.27070(8) 0.69585(16) 0.0178(4) Uani d . 1 1
C C6 0.6178(3) 0.31080(8) 0.61605(16) 0.0164(4) Uani d . 1 1
C C7 0.6633(4) 0.21941(8) 0.68785(19) 0.0252(5) Uani d . 1 1
H H7 0.6189 0.1908 0.7396 0.030 Uiso calc R 1 1
C C8 0.8387(4) 0.20906(9) 0.60743(19) 0.0283(5) Uani d . 1 1
H H8 0.9121 0.1738 0.6041 0.034 Uiso calc R 1 1
C C9 0.9075(4) 0.25027(9) 0.53148(19) 0.0270(5) Uani d . 1 1
H H9 1.0302 0.2436 0.4770 0.032 Uiso calc R 1 1
C C10 0.7963(3) 0.30103(8) 0.53575(17) 0.0201(4) Uani d . 1 1
H H10 0.8419 0.3294 0.4837 0.024 Uiso calc R 1 1
C C11 0.4745(4) 0.40282(8) 0.94024(17) 0.0227(4) Uani d . 1 1
H H11 0.3804 0.3928 1.0050 0.027 Uiso calc R 1 1
C C12 0.6633(4) 0.44207(8) 0.95966(18) 0.0246(5) Uani d . 1 1
H H12 0.6994 0.4583 1.0381 0.030 Uiso calc R 1 1
C C13 0.7997(4) 0.45781(8) 0.86587(17) 0.0231(4) Uani d . 1 1
H H13 0.9279 0.4849 0.8799 0.028 Uiso calc R 1 1
C C14 0.7491(3) 0.43393(8) 0.75109(17) 0.0188(4) Uani d . 1 1
H H14 0.8412 0.4445 0.6859 0.023 Uiso calc R 1 1
C C15 0.3652(3) 0.38528(7) 0.52315(16) 0.0156(4) Uani d . 1 1
H H1 0.284(5) 0.3755(11) 0.355(2) 0.059(8) Uiso d . 1 1
H H1N 0.288(4) 0.4565(10) 0.586(2) 0.036(7) Uiso d . 1 1
H H1W 0.112(5) 0.4259(11) 0.239(2) 0.055(8) Uiso d . 1 1
H H2N 0.150(4) 0.4426(9) 0.463(2) 0.033(6) Uiso d . 1 1
H H2W 0.381(5) 0.4265(11) 0.244(2) 0.058(9) Uiso d . 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C15 O1 H1 110.2(16) ?
H1W O1W H2W 106(2) ?
C15 N1 C6 120.69(14) y
C15 N1 C1 122.19(15) y
C6 N1 C1 116.77(14) y
C15 N2 H1N 124.8(15) ?
C15 N2 H2N 116.1(15) ?
H1N N2 H2N 119(2) ?
C14 C1 C2 122.59(16) ?
C14 C1 N1 120.50(16) ?
C2 C1 N1 116.75(16) ?
C1 C2 C11 117.89(17) ?
C1 C2 C3 118.43(16) ?
C11 C2 C3 123.59(17) ?
C2 C3 C4 111.75(15) ?
C2 C3 H3A 109.3 ?
C4 C3 H3A 109.3 ?
C2 C3 H3B 109.3 ?
C4 C3 H3B 109.3 ?
H3A C3 H3B 107.9 ?
C5 C4 C3 118.47(16) ?
C5 C4 H4A 107.7 ?
C3 C4 H4A 107.7 ?
C5 C4 H4B 107.7 ?
C3 C4 H4B 107.7 ?
H4A C4 H4B 107.1 ?
C6 C5 C7 116.23(17) ?
C6 C5 C4 126.58(17) ?
C7 C5 C4 117.18(17) ?
C10 C6 C5 121.94(18) ?
C10 C6 N1 117.25(17) ?
C5 C6 N1 120.72(16) ?
C8 C7 C5 122.31(19) ?
C8 C7 H7 118.8 ?
C5 C7 H7 118.8 ?
C7 C8 C9 119.86(19) ?
C7 C8 H8 120.1 ?
C9 C8 H8 120.1 ?
C10 C9 C8 119.46(19) ?
C10 C9 H9 120.3 ?
C8 C9 H9 120.3 ?
C9 C10 C6 120.18(19) ?
C9 C10 H10 119.9 ?
C6 C10 H10 119.9 ?
C12 C11 C2 120.39(18) ?
C12 C11 H11 119.8 ?
C2 C11 H11 119.8 ?
C13 C12 C11 120.62(18) ?
C13 C12 H12 119.7 ?
C11 C12 H12 119.7 ?
C12 C13 C14 119.98(18) ?
C12 C13 H13 120.0 ?
C14 C13 H13 120.0 ?
C1 C14 C13 118.52(18) ?
C1 C14 H14 120.7 ?
C13 C14 H14 120.7 ?
O1 C15 N2 121.44(17) y
O1 C15 N1 117.00(16) y
N2 C15 N1 121.53(17) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C15 1.297(2) y
O1 H1 0.97(3) ?
O1W H1W 0.92(3) ?
O1W H2W 0.86(3) ?
N1 C15 1.339(2) y
N1 C6 1.444(2) y
N1 C1 1.449(2) y
N2 C15 1.314(2) y
N2 H1N 0.86(2) ?
N2 H2N 0.89(2) ?
C1 C14 1.384(3) ?
C1 C2 1.388(2) ?
C2 C11 1.392(3) ?
C2 C3 1.502(3) ?
C3 C4 1.533(3) ?
C3 H3A 0.9900 ?
C3 H3B 0.9900 ?
C4 C5 1.518(3) ?
C4 H4A 0.9900 ?
C4 H4B 0.9900 ?
C5 C6 1.396(3) ?
C5 C7 1.404(3) ?
C6 C10 1.390(3) ?
C7 C8 1.381(3) ?
C7 H7 0.9500 ?
C8 C9 1.387(3) ?
C8 H8 0.9500 ?
C9 C10 1.379(3) ?
C9 H9 0.9500 ?
C10 H10 0.9500 ?
C11 C12 1.387(3) ?
C11 H11 0.9500 ?
C12 C13 1.384(3) ?
C12 H12 0.9500 ?
C13 C14 1.390(3) ?
C13 H13 0.9500 ?
C14 H14 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 O1W . 0.97(3) 1.51(3) 2.4807(18) 173(3)
N2 H1N Cl1 . 0.86(2) 2.42(3) 3.2151(19) 153(2)
N2 H2N Cl1 3_566 0.89(2) 2.45(2) 3.3192(18) 168.9(19)
O1W H1W Cl1 3_566 0.92(3) 2.17(3) 3.0513(16) 159(2)
O1W H2W Cl1 3_666 0.86(3) 2.29(3) 3.1084(16) 159(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
C15 N1 C1 C14 -85.0(2)
C6 N1 C1 C14 101.7(2)
C15 N1 C1 C2 99.4(2)
C6 N1 C1 C2 -73.8(2)
C14 C1 C2 C11 0.3(3)
N1 C1 C2 C11 175.75(16)
C14 C1 C2 C3 -176.46(17)
N1 C1 C2 C3 -1.0(2)
C1 C2 C3 C4 71.6(2)
C11 C2 C3 C4 -105.0(2)
C2 C3 C4 C5 -57.9(2)
C3 C4 C5 C6 1.5(3)
C3 C4 C5 C7 -179.22(16)
C7 C5 C6 C10 -1.9(2)
C4 C5 C6 C10 177.41(16)
C7 C5 C6 N1 -178.36(15)
C4 C5 C6 N1 0.9(3)
C15 N1 C6 C10 68.2(2)
C1 N1 C6 C10 -118.44(17)
C15 N1 C6 C5 -115.18(19)
C1 N1 C6 C5 58.2(2)
C6 C5 C7 C8 1.1(3)
C4 C5 C7 C8 -178.24(17)
C5 C7 C8 C9 0.3(3)
C7 C8 C9 C10 -1.1(3)
C8 C9 C10 C6 0.3(3)
C5 C6 C10 C9 1.2(3)
N1 C6 C10 C9 177.79(16)
C1 C2 C11 C12 -0.9(3)
C3 C2 C11 C12 175.67(18)
C2 C11 C12 C13 1.0(3)
C11 C12 C13 C14 -0.4(3)
C2 C1 C14 C13 0.2(3)
N1 C1 C14 C13 -175.05(16)
C12 C13 C14 C1 -0.2(3)
C6 N1 C15 O1 -0.9(2)
C1 N1 C15 O1 -173.93(15)
C6 N1 C15 N2 177.44(17)
C1 N1 C15 N2 4.5(3)
