#------------------------------------------------------------------------------
#$Date: 2017-12-10 04:32:44 +0200 (Sun, 10 Dec 2017) $
#$Revision: 204128 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/41/1514130.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1514130
loop_
_publ_author_name
'Zencirci, Neslihan'
'Griesser, Ulrich J.'
'Gelbrich, Thomas'
'Kahlenberg, Volker'
'Jetti, Ram K. R.'
'Apperley, David C.'
'Harris, Robin K.'
_publ_section_title
;
 New solvates of an old drug compound (phenobarbital): structure and
 stability.
;
_journal_issue                   12
_journal_name_full               'The journal of physical chemistry. B'
_journal_page_first              3267
_journal_page_last               3280
_journal_paper_doi               10.1021/jp409201v
_journal_volume                  118
_journal_year                    2014
_chemical_formula_moiety         'C12 H12 N2 O3, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C14 H16 N2 O4'
_chemical_formula_weight         276.29
_chemical_name_common            'phenobarbital dioxane hemisolvate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2009-08-19T18:24:38-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 98.071(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.86417(15)
_cell_length_b                   11.9645(2)
_cell_length_c                   16.6842(4)
_cell_measurement_reflns_used    4290
_cell_measurement_temperature    253(2)
_cell_measurement_theta_max      28.444
_cell_measurement_theta_min      2.9904
_cell_volume                     1356.64(5)
_computing_cell_refinement
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
        (compiled May  6 2009,17:20:42)
;
_computing_data_collection
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
        (compiled May  6 2009,17:20:42)
;
_computing_data_reduction
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
        (compiled May  6 2009,17:20:42)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      253(2)
_diffrn_detector_area_resol_mean 10.3575
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8534
_diffrn_reflns_theta_full        26
_diffrn_reflns_theta_max         26
_diffrn_reflns_theta_min         3
_exptl_absorpt_coefficient_mu    0.1
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Oxford Diffraction Ltd.,
        Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET)
        (compiled May  6 2009,17:20:42)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0187(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2655
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.955
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0309
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0474P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0781
_reflns_number_gt                1997
_reflns_number_total             2655
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp409201v_si_002.cif
_cod_data_source_block           Pbtl_dioxane_hemisolvate_09thg000
_cod_database_code               1514130
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'
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
N1 N 0.50881(14) 0.15949(8) 0.17356(6) 0.0235(2) Uani 1 1 d D
H1 H 0.3835(13) 0.1588(11) 0.1727(8) 0.033(4) Uiso 1 1 d D
N3 N 0.77559(13) 0.25772(8) 0.13546(6) 0.0228(2) Uani 1 1 d .
H3 H 0.818(2) 0.3153(12) 0.1113(9) 0.036(4) Uiso 1 1 d .
O2 O 0.46496(12) 0.31806(7) 0.09877(6) 0.0353(3) Uani 1 1 d .
O4 O 1.08839(11) 0.20522(6) 0.17150(5) 0.0283(2) Uani 1 1 d .
O6 O 0.54758(12) 0.00100(7) 0.24656(5) 0.0327(2) Uani 1 1 d .
C2 C 0.57501(16) 0.24968(9) 0.13352(7) 0.0225(3) Uani 1 1 d .
C4 C 0.91450(16) 0.18621(8) 0.17174(7) 0.0193(3) Uani 1 1 d .
C5 C 0.84453(16) 0.08124(8) 0.21165(7) 0.0195(3) Uani 1 1 d .
C6 C 0.62183(17) 0.07587(9) 0.21275(7) 0.0219(3) Uani 1 1 d .
C7 C 0.94412(17) 0.08217(9) 0.30022(8) 0.0246(3) Uani 1 1 d .
H7A H 0.9087 0.013 0.3274 0.029(3) Uiso 1 1 calc R
H7B H 1.0887 0.0828 0.3014 0.029(3) Uiso 1 1 calc R
C8 C 0.88308(19) 0.18341(10) 0.34663(8) 0.0312(3) Uani 1 1 d .
H8A H 0.9181 0.2521 0.32 0.044(4) Uiso 1 1 calc R
H8B H 0.9514 0.1815 0.4023 0.041(4) Uiso 1 1 calc R
H8C H 0.7406 0.1815 0.3474 0.046(4) Uiso 1 1 calc R
C9 C 0.90299(16) -0.01689(9) 0.16074(8) 0.0228(3) Uani 1 1 d .
C10 C 0.8011(2) -0.03413(11) 0.08403(9) 0.0372(3) Uani 1 1 d .
H10 H 0.6909 0.0116 0.0653 0.053(4) Uiso 1 1 calc R
C11 C 0.8577(3) -0.11719(11) 0.03419(10) 0.0471(4) Uani 1 1 d .
H11 H 0.7863 -0.1282 -0.0183 0.061(5) Uiso 1 1 calc R
C12 C 1.0165(2) -0.18346(10) 0.06057(11) 0.0466(4) Uani 1 1 d .
H12 H 1.0569 -0.2396 0.0262 0.055(4) Uiso 1 1 calc R
C13 C 1.1167(2) -0.16837(12) 0.13673(12) 0.0509(4) Uani 1 1 d .
H13 H 1.2252 -0.2153 0.1554 0.070(5) Uiso 1 1 calc R
C14 C 1.06121(19) -0.08511(10) 0.18703(10) 0.0384(4) Uani 1 1 d .
H14 H 1.1324 -0.0751 0.2396 0.052(5) Uiso 1 1 calc R
O1S O 0.90197(11) 0.43666(6) 0.05228(5) 0.0251(2) Uani 1 1 d .
C1S C 0.79539(17) 0.50653(9) -0.00845(7) 0.0240(3) Uani 1 1 d .
H1S1 H 0.7754 0.5812 0.0147 0.025(3) Uiso 1 1 calc R
H1S2 H 0.6645 0.4734 -0.0267 0.029(3) Uiso 1 1 calc R
C2S C 1.09346(16) 0.48180(9) 0.07899(8) 0.0238(3) Uani 1 1 d .
H2S1 H 1.1661 0.4317 0.12 0.034(4) Uiso 1 1 calc R
H2S2 H 1.0807 0.5558 0.1043 0.023(3) Uiso 1 1 calc R
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 0 '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 0.006 '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_site_symmetry_1
_geom_angle_site_symmetry_3
C6 N1 C2 126.71(9) . .
C6 N1 H1 119.9(9) . .
C2 N1 H1 113.4(9) . .
C4 N3 C2 127.15(10) . .
C4 N3 H3 116.6(9) . .
C2 N3 H3 116.3(9) . .
O2 C2 N3 121.41(10) . .
O2 C2 N1 122.49(10) . .
N3 C2 N1 116.10(10) . .
O4 C4 N3 120.58(10) . .
O4 C4 C5 121.56(9) . .
N3 C4 C5 117.86(9) . .
C4 C5 C6 114.46(9) . .
C4 C5 C9 105.34(9) . .
C6 C5 C9 108.25(9) . .
C4 C5 C7 106.72(9) . .
C6 C5 C7 107.35(9) . .
C9 C5 C7 114.93(9) . .
O6 C6 N1 120.98(10) . .
O6 C6 C5 121.55(10) . .
N1 C6 C5 117.46(9) . .
C8 C7 C5 112.10(9) . .
C8 C7 H7A 109.2 . .
C5 C7 H7A 109.2 . .
C8 C7 H7B 109.2 . .
C5 C7 H7B 109.2 . .
H7A C7 H7B 107.9 . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C14 C9 C10 118.58(11) . .
C14 C9 C5 122.12(11) . .
C10 C9 C5 119.20(10) . .
C9 C10 C11 120.91(13) . .
C9 C10 H10 119.5 . .
C11 C10 H10 119.5 . .
C12 C11 C10 119.98(15) . .
C12 C11 H11 120 . .
C10 C11 H11 120 . .
C11 C12 C13 119.69(13) . .
C11 C12 H12 120.2 . .
C13 C12 H12 120.2 . .
C12 C13 C14 120.70(14) . .
C12 C13 H13 119.7 . .
C14 C13 H13 119.7 . .
C9 C14 C13 120.13(14) . .
C9 C14 H14 119.9 . .
C13 C14 H14 119.9 . .
C1S O1S C2S 110.79(8) . .
O1S C1S C2S 110.16(9) . 3_765
O1S C1S H1S1 109.6 . .
C2S C1S H1S1 109.6 3_765 .
O1S C1S H1S2 109.6 . .
C2S C1S H1S2 109.6 3_765 .
H1S1 C1S H1S2 108.1 . .
O1S C2S C1S 109.71(10) . 3_765
O1S C2S H2S1 109.7 . .
C1S C2S H2S1 109.7 3_765 .
O1S C2S H2S2 109.7 . .
C1S C2S H2S2 109.7 3_765 .
H2S1 C2S H2S2 108.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C6 1.3740(15) .
N1 C2 1.3792(14) .
N1 H1 0.859(8) .
N3 C4 1.3585(14) .
N3 C2 1.3760(14) .
N3 H3 0.868(15) .
O2 C2 1.2055(13) .
O4 C4 1.2157(13) .
O6 C6 1.2087(13) .
C4 C5 1.5301(15) .
C5 C6 1.5327(15) .
C5 C9 1.5352(15) .
C5 C7 1.5386(17) .
C7 C8 1.5276(16) .
C7 H7A 0.99 .
C7 H7B 0.99 .
C8 H8A 0.98 .
C8 H8B 0.98 .
C8 H8C 0.98 .
C9 C14 1.3800(17) .
C9 C10 1.3851(18) .
C10 C11 1.3858(19) .
C10 H10 0.95 .
C11 C12 1.370(2) .
C11 H11 0.95 .
C12 C13 1.369(2) .
C12 H12 0.95 .
C13 C14 1.390(2) .
C13 H13 0.95 .
C14 H14 0.95 .
O1S C1S 1.4327(14) .
O1S C2S 1.4330(14) .
C1S C2S 1.4963(17) 3_765
C1S H1S1 0.99 .
C1S H1S2 0.99 .
C2S C1S 1.4963(17) 3_765
C2S H2S1 0.99 .
C2S H2S2 0.99 .
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
N1 H1 O4 0.859(8) 2.097(9) 2.9326(12) 164.1(12) 1_455
N3 H3 O1S 0.868(15) 1.891(15) 2.7568(12) 176.2(14) .
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_4
C4 N3 C2 O2 -179.46(11) .
C4 N3 C2 N1 0.66(17) .
C6 N1 C2 O2 178.03(12) .
C6 N1 C2 N3 -2.09(17) .
C2 N3 C4 O4 -177.28(11) .
C2 N3 C4 C5 3.41(17) .
O4 C4 C5 C6 174.90(11) .
N3 C4 C5 C6 -5.79(15) .
O4 C4 C5 C9 -66.30(14) .
N3 C4 C5 C9 113.00(11) .
O4 C4 C5 C7 56.30(14) .
N3 C4 C5 C7 -124.39(11) .
C2 N1 C6 O6 179.39(11) .
C2 N1 C6 C5 -0.77(17) .
C4 C5 C6 O6 -175.57(11) .
C9 C5 C6 O6 67.29(14) .
C7 C5 C6 O6 -57.32(14) .
C4 C5 C6 N1 4.59(15) .
C9 C5 C6 N1 -112.55(11) .
C7 C5 C6 N1 122.84(11) .
C4 C5 C7 C8 62.24(11) .
C6 C5 C7 C8 -60.91(11) .
C9 C5 C7 C8 178.62(9) .
C4 C5 C9 C14 104.32(12) .
C6 C5 C9 C14 -132.81(12) .
C7 C5 C9 C14 -12.84(15) .
C4 C5 C9 C10 -71.98(13) .
C6 C5 C9 C10 50.88(14) .
C7 C5 C9 C10 170.85(10) .
C14 C9 C10 C11 -0.71(19) .
C5 C9 C10 C11 175.72(11) .
C9 C10 C11 C12 -0.1(2) .
C10 C11 C12 C13 1.0(2) .
C11 C12 C13 C14 -1.2(2) .
C10 C9 C14 C13 0.56(19) .
C5 C9 C14 C13 -175.77(12) .
C12 C13 C14 C9 0.4(2) .
C2S O1S C1S C2S 58.42(13) 3_765
C1S O1S C2S C1S -58.15(12) 3_765
