#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:31:26 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180185 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/81/7108157.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_7108157
loop_
_publ_author_name
'Dario Braga'
'Fabrizia Grepioni'
'Lucia Maini'
'Davide Capucci'
'Saverio Nanna'
'Johan Wouters'
'Luc Aerts'
'Luc Quere'
_publ_section_title
;
 Combining piracetam and lithium salts: ionic co-crystals and co-drugs?
;
_journal_name_full               Chem.Commun.
_journal_page_first              8219
_journal_paper_doi               10.1039/c2cc33855f
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C6 H14 Br Li N2 O4'
_chemical_formula_weight         265.04
_chemical_name_common            'piracetam LiBr 2H2O'
_chemical_name_systematic
;
?
;
_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                 90.404(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7723(5)
_cell_length_b                   9.8812(7)
_cell_length_c                   14.8483(11)
_cell_measurement_reflns_used    1823
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1940
_cell_measurement_theta_min      2.7381
_cell_volume                     1140.32(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1340
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6234
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.98
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    3.595
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2461
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0488
_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)+(0.0332P)²+0.7563P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0949
_reflns_number_gt                1868
_reflns_number_total             2461
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c2cc33855f.txt
_cod_data_source_block           PIR.LiBr.2H2O
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7108157
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_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
Li1 Li -0.5605(8) 0.6592(6) 0.7232(4) 0.0393(14) Uani 1 1 d .
Br1 Br 0.06739(5) 0.13894(4) 0.34945(3) 0.05110(16) Uani 1 1 d .
C1 C -0.6422(4) 0.1523(3) 0.5989(2) 0.0360(8) Uani 1 1 d .
O1 O -0.5694(3) 0.1150(2) 0.66867(16) 0.0447(6) Uani 1 1 d .
N1 N -0.7709(5) 0.0849(4) 0.5624(3) 0.0546(10) Uani 1 1 d .
H1A H -0.811(6) 0.106(4) 0.508(3) 0.066 Uiso 1 1 d .
H1B H -0.820(5) 0.018(4) 0.596(3) 0.066 Uiso 1 1 d .
C2 C -0.5947(5) 0.2815(4) 0.5507(2) 0.0453(10) Uani 1 1 d .
H2A H -0.6064 0.2672 0.4863 0.054 Uiso 1 1 calc R
H2B H -0.6753 0.3518 0.5677 0.054 Uiso 1 1 calc R
N2 N -0.4243(4) 0.3275(3) 0.56971(19) 0.0363(7) Uani 1 1 d .
C3 C -0.2732(5) 0.2578(4) 0.5372(3) 0.0564(11) Uani 1 1 d .
H3A H -0.2800 0.2435 0.4726 0.068 Uiso 1 1 calc R
H3B H -0.2585 0.1712 0.5669 0.068 Uiso 1 1 calc R
C4 C -0.1280(7) 0.3540(5) 0.5613(4) 0.0918(18) Uani 1 1 d .
H4A H -0.0363 0.3060 0.5924 0.110 Uiso 1 1 calc R
H4B H -0.0812 0.3950 0.5074 0.110 Uiso 1 1 calc R
C5 C -0.2034(5) 0.4600(4) 0.6212(3) 0.0586(12) Uani 1 1 d .
H5A H -0.1649 0.4474 0.6829 0.070 Uiso 1 1 calc R
H5B H -0.1700 0.5497 0.6014 0.070 Uiso 1 1 calc R
C6 C -0.3921(5) 0.4425(3) 0.6139(2) 0.0365(8) Uani 1 1 d .
O2 O -0.5033(4) 0.5184(3) 0.64182(17) 0.0524(7) Uani 1 1 d .
O2W O -0.4894(3) 0.8312(2) 0.67647(17) 0.0470(6) Uani 1 1 d .
H200 H -0.3541 0.8248 0.6628 0.056 Uiso 1 1 d .
H201 H -0.5553 0.9155 0.6703 0.056 Uiso 1 1 d .
O1W O -0.8014(4) 0.6442(4) 0.7427(3) 0.0725(9) Uani 1 1 d D
H100 H -0.883(5) 0.695(4) 0.719(3) 0.082(16) Uiso 1 1 d D
H101 H -0.848(6) 0.569(3) 0.763(3) 0.11(2) Uiso 1 1 d D
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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Li Li -0.0003 0.0001 '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 0.0060 '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_3
O2 Li1 O1W 105.9(3) .
O2 Li1 O2W 110.5(3) .
O1W Li1 O2W 114.2(3) .
O2 Li1 O1 103.8(3) 2_456
O1W Li1 O1 111.3(3) 2_456
O2W Li1 O1 110.5(3) 2_456
O1 C1 N1 122.6(3) .
O1 C1 C2 122.5(3) .
N1 C1 C2 114.9(3) .
C1 O1 Li1 149.4(3) 2_446
C1 N1 H1A 121(3) .
C1 N1 H1B 117(3) .
H1A N1 H1B 121(4) .
N2 C2 C1 113.9(3) .
N2 C2 H2A 108.8 .
C1 C2 H2A 108.8 .
N2 C2 H2B 108.8 .
C1 C2 H2B 108.8 .
H2A C2 H2B 107.7 .
C6 N2 C2 122.6(3) .
C6 N2 C3 114.8(3) .
C2 N2 C3 122.5(3) .
N2 C3 C4 103.2(3) .
N2 C3 H3A 111.1 .
C4 C3 H3A 111.1 .
N2 C3 H3B 111.1 .
C4 C3 H3B 111.1 .
H3A C3 H3B 109.1 .
C5 C4 C3 106.5(4) .
C5 C4 H4A 110.4 .
C3 C4 H4A 110.4 .
C5 C4 H4B 110.4 .
C3 C4 H4B 110.4 .
H4A C4 H4B 108.6 .
C6 C5 C4 105.5(3) .
C6 C5 H5A 110.6 .
C4 C5 H5A 110.6 .
C6 C5 H5B 110.6 .
C4 C5 H5B 110.6 .
H5A C5 H5B 108.8 .
O2 C6 N2 124.0(3) .
O2 C6 C5 127.5(3) .
N2 C6 C5 108.5(3) .
C6 O2 Li1 146.8(3) .
Li1 O2W H200 107.5 .
Li1 O2W H201 129.4 .
H200 O2W H201 122.9 .
Li1 O1W H100 127(3) .
Li1 O1W H101 122(4) .
H100 O1W H101 108(5) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Li1 O2 1.898(6) .
Li1 O1W 1.903(7) .
Li1 O2W 1.919(6) .
Li1 O1 1.940(6) 2_456
C1 O1 1.233(4) .
C1 N1 1.315(5) .
C1 C2 1.511(5) .
O1 Li1 1.940(6) 2_446
N1 H1A 0.88(4) .
N1 H1B 0.91(4) .
C2 N2 1.426(4) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
N2 C6 1.335(4) .
N2 C3 1.447(5) .
C3 C4 1.516(6) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C5 1.496(6) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C6 1.480(5) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 O2 1.219(4) .
O2W H200 1.0744 .
O2W H201 0.9817 .
O1W H100 0.882(19) .
O1W H101 0.88(2) .
