#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/57/2205761.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_2205761
loop_
_publ_author_name
'Hempel, Andrew'
'Camerman, Norman'
'Camerman, Arthur'
'Mastropaolo, Donald'
_publ_section_title
;
 Nafimidone monohydrate: an imidazole anticonvulsant
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1387
_journal_page_last               o1389
_journal_paper_doi               10.1107/S1600536805011487
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C15 H12 N2 O , H2 O'
_chemical_formula_moiety         'C15 H12 N2 O , H2 O'
_chemical_formula_sum            'C15 H14 N2 O2'
_chemical_formula_weight         254.28
_chemical_name_common            'Nafimidone monohydrate'
_chemical_name_systematic
;
2-(1H-imidazol-1-yl)-1-(2-naphthyl)ethanone monohydrate
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_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                 90.15(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.597(3)
_cell_length_b                   14.213(3)
_cell_length_c                   7.827(2)
_cell_measurement_reflns_used    32
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      49
_cell_measurement_theta_min      28
_cell_volume                     1290.1(5)
_computing_cell_refinement       'Picker Operating Manual'
_computing_data_collection       'Picker Operating Manual (Picker, 1967)'
_computing_data_reduction        'DATRDN in the XRAY System (Stewart, 1978)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELX97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Picker FACS-1 four-circle'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  'Ni-filtered radiation'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0076
_diffrn_reflns_av_sigmaI/netI    3.7354
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2310
_diffrn_reflns_theta_full        65.00
_diffrn_reflns_theta_max         65.00
_diffrn_reflns_theta_min         3.81
_diffrn_standards_decay_%        0.9
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.717
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.911
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.139
_refine_ls_extinction_coef       0.0035(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2197
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.917
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0550
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0477P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1517
_refine_ls_wR_factor_ref         0.1743
_reflns_number_gt                1328
_reflns_number_total             2197
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6406.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21 /c'
_cod_database_code               2205761
_cod_database_fobs_code          2205761
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_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_type_symbol
C1 0.4132(2) 0.62187(19) -0.0803(3) 0.0556(7) Uani d . 1 C
H1 0.3480 0.6143 -0.1485 0.080(3) Uiso calc R 1 H
C2 0.4002(2) 0.64163(19) 0.0896(3) 0.0548(7) Uani d . 1 C
C3 0.4995(3) 0.6556(2) 0.1930(4) 0.0609(8) Uani d . 1 C
H3 0.4911 0.6706 0.3080 0.080(3) Uiso calc R 1 H
C4 0.6067(2) 0.6473(2) 0.1250(4) 0.0622(8) Uani d . 1 C
H4 0.6709 0.6556 0.1948 0.080(3) Uiso calc R 1 H
C5 0.7327(3) 0.6173(2) -0.1247(4) 0.0705(9) Uani d . 1 C
H5 0.7984 0.6249 -0.0577 0.080(3) Uiso calc R 1 H
C6 0.7436(3) 0.5977(2) -0.2936(4) 0.0742(9) Uani d . 1 C
H6 0.8167 0.5929 -0.3413 0.080(3) Uiso calc R 1 H
C7 0.6461(3) 0.5847(2) -0.3969(4) 0.0735(9) Uani d . 1 C
H7 0.6548 0.5712 -0.5125 0.080(3) Uiso calc R 1 H
C8 0.5390(3) 0.5918(2) -0.3286(4) 0.0657(8) Uani d . 1 C
H8 0.4747 0.5828 -0.3979 0.080(3) Uiso calc R 1 H
C9 0.5239(2) 0.61274(18) -0.1542(3) 0.0529(7) Uani d . 1 C
C10 0.6224(2) 0.62625(19) -0.0492(4) 0.0564(7) Uani d . 1 C
N11 0.0735(2) 0.64095(18) 0.1539(3) 0.0608(7) Uani d . 1 N
C12 0.0173(3) 0.5630(2) 0.2030(4) 0.0737(9) Uani d . 1 C
H12 0.0403 0.5025 0.1734 0.080(3) Uiso calc R 1 H
N13 -0.0729(2) 0.5812(2) 0.2969(4) 0.0777(8) Uani d . 1 N
C14 -0.0748(3) 0.6760(3) 0.3081(4) 0.0735(9) Uani d . 1 C
H14 -0.1300 0.7102 0.3677 0.080(3) Uiso calc R 1 H
C15 0.0137(3) 0.7145(2) 0.2218(4) 0.0689(9) Uani d . 1 C
H15 0.0306 0.7781 0.2108 0.080(3) Uiso calc R 1 H
C16 0.2854(2) 0.64984(19) 0.1712(3) 0.0556(7) Uani d . 1 C
C17 0.1795(3) 0.6448(3) 0.0574(4) 0.0720(9) Uani d . 1 C
H17A 0.1779 0.6995 -0.0166 0.080(3) Uiso calc R 1 H
H17B 0.1847 0.5893 -0.0145 0.080(3) Uiso calc R 1 H
O18 0.27471(18) 0.66121(15) 0.3234(2) 0.0735(7) Uani d . 1 O
O19 0.1823(3) 0.5938(2) 0.6438(3) 0.0899(9) Uani d . 1 O
H191 0.196(5) 0.608(4) 0.550(7) 0.161(15) Uiso d . 1 H
H192 0.148(4) 0.527(4) 0.644(6) 0.161(15) Uiso d . 1 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_site_symmetry_1
_geom_angle
C2 C1 C9 . 121.2(3)
C2 C1 H1 . 119.4
C9 C1 H1 . 119.4
C1 C2 C3 . 119.4(3)
C1 C2 C16 . 122.4(3)
C3 C2 C16 . 118.1(2)
C4 C3 C2 . 120.4(3)
C4 C3 H3 . 119.8
C2 C3 H3 . 119.8
C3 C4 C10 . 121.3(3)
C3 C4 H4 . 119.4
C10 C4 H4 . 119.4
C6 C5 C10 . 120.7(3)
C6 C5 H5 . 119.6
C10 C5 H5 . 119.6
C5 C6 C7 . 120.8(3)
C5 C6 H6 . 119.6
C7 C6 H6 . 119.6
C8 C7 C6 . 120.0(3)
C8 C7 H7 . 120.0
C6 C7 H7 . 120.0
C7 C8 C9 . 120.9(3)
C7 C8 H8 . 119.5
C9 C8 H8 . 119.5
C8 C9 C1 . 122.0(3)
C8 C9 C10 . 119.2(3)
C1 C9 C10 . 118.8(2)
C4 C10 C5 . 122.8(3)
C4 C10 C9 . 118.9(3)
C5 C10 C9 . 118.3(3)
C12 N11 C15 . 105.9(3)
C12 N11 C17 . 126.5(3)
C15 N11 C17 . 127.5(3)
N13 C12 N11 . 112.9(3)
N13 C12 H12 . 123.6
N11 C12 H12 . 123.6
C12 N13 C14 . 104.3(3)
C15 C14 N13 . 111.1(3)
C15 C14 H14 . 124.4
N13 C14 H14 . 124.4
C14 C15 N11 . 105.9(3)
C14 C15 H15 . 127.1
N11 C15 H15 . 127.1
O18 C16 C2 1 122.0(3)
O18 C16 C2 . 122.0(3)
O18 C16 C17 1 120.0(3)
O18 C16 C17 . 120.0(3)
C2 C16 C17 . 118.0(2)
N11 C17 C16 . 112.6(2)
N11 C17 H17A . 109.1
C16 C17 H17A . 109.1
N11 C17 H17B . 109.1
C16 C17 H17B . 109.1
H17A C17 H17B . 107.8
H191 O19 H192 . 109(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.367(4)
C1 C9 . 1.416(4)
C1 H1 . 0.9300
C2 C3 . 1.420(4)
C2 C16 . 1.482(4)
C3 C4 . 1.359(4)
C3 H3 . 0.9300
C4 C10 . 1.408(4)
C4 H4 . 0.9300
C5 C6 . 1.357(4)
C5 C10 . 1.416(4)
C5 H5 . 0.9300
C6 C7 . 1.401(5)
C6 H6 . 0.9300
C7 C8 . 1.358(4)
C7 H7 . 0.9300
C8 C9 . 1.408(4)
C8 H8 . 0.9300
C9 C10 . 1.418(4)
N11 C12 . 1.342(4)
N11 C15 . 1.363(4)
N11 C17 . 1.446(3)
C12 N13 . 1.307(4)
C12 H12 . 0.9300
N13 C14 . 1.351(4)
C14 C15 . 1.346(4)
C14 H14 . 0.9300
C15 H15 . 0.9300
C16 O18 1 1.209(3)
C16 O18 . 1.209(3)
C16 C17 . 1.517(4)
C17 H17A . 0.9700
C17 H17B . 0.9700
O19 H191 . 0.78(6)
O19 H192 . 1.02(5)
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
O19 H191 O18 1 0.78(6) 2.13(6) 2.893(3) 165(6)
O19 H192 N13 3_566 1.02(5) 1.83(5) 2.830(4) 164(4)
C1 H1 O19 1_554 0.93 2.53 3.458(4) 175.1
C15 H15 O19 2_564 0.93 2.59 3.411(5) 147.9
C17 H17A O18 2_564 0.97 2.60 3.491(4) 153.0
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C9 C1 C2 C3 . . 1.6(4)
C9 C1 C2 C16 . . -178.8(3)
C1 C2 C3 C4 . . -1.6(4)
C16 C2 C3 C4 . . 178.9(3)
C2 C3 C4 C10 . . 1.1(4)
C10 C5 C6 C7 . . -0.8(5)
C5 C6 C7 C8 . . 0.2(5)
C6 C7 C8 C9 . . 0.3(5)
C7 C8 C9 C1 . . 179.1(3)
C7 C8 C9 C10 . . -0.1(4)
C2 C1 C9 C8 . . 179.6(3)
C2 C1 C9 C10 . . -1.2(4)
C3 C4 C10 C5 . . 179.8(3)
C3 C4 C10 C9 . . -0.7(4)
C6 C5 C10 C4 . . -179.5(3)
C6 C5 C10 C9 . . 1.0(4)
C8 C9 C10 C4 . . 179.9(3)
C1 C9 C10 C4 . . 0.7(4)
C8 C9 C10 C5 . . -0.5(4)
C1 C9 C10 C5 . . -179.8(3)
C15 N11 C12 N13 . . -0.2(4)
C17 N11 C12 N13 . . 176.5(3)
N11 C12 N13 C14 . . 0.1(4)
C12 N13 C14 C15 . . -0.1(4)
N13 C14 C15 N11 . . 0.0(4)
C12 N11 C15 C14 . . 0.1(3)
C17 N11 C15 C14 . . -176.5(3)
C1 C2 C16 O18 . 1 175.1(3)
C3 C2 C16 O18 . 1 -5.4(4)
C1 C2 C16 O18 . . 175.1(3)
C3 C2 C16 O18 . . -5.4(4)
C1 C2 C16 C17 . . -5.7(4)
C3 C2 C16 C17 . . 173.9(3)
C12 N11 C17 C16 . . -92.7(4)
C15 N11 C17 C16 . . 83.2(4)
O18 C16 C17 N11 1 . -8.5(4)
O18 C16 C17 N11 . . -8.5(4)
C2 C16 C17 N11 . . 172.2(3)
C2 C16 O18 O18 . 1 0.0(17)
C17 C16 O18 O18 . 1 0.0(16)
