#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/12/7211222.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_7211222
loop_
_publ_author_name
'Wouters, Johan'
'Grepioni, Fabrizia'
'Braga, Dario'
'Kaminski, Rafal M.'
'Rome, Sandrine'
'Aerts, Luc'
'Quéré, Luc'
_publ_section_title
;
 Novel pharmaceutical compositions through co-crystallization of racetams
 and Li+ salts
;
_journal_issue                   44
_journal_name_full               CrystEngComm
_journal_page_first              8898
_journal_paper_doi               10.1039/c3ce41539b
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C22 H40 Li N4 O4, Br'
_chemical_formula_sum            'C22 H40 Br Li N4 O4'
_chemical_formula_weight         511.42
_space_group_IT_number           20
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      20
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.408(2)
_cell_length_b                   25.175(3)
_cell_length_c                   10.745(2)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      37.6
_cell_measurement_theta_min      20.2
_cell_volume                     2815.4(8)
_computing_cell_refinement       NoniusCAD4/MACH3(2000)
_computing_data_collection       NoniusCAD4/MACH3(2000)
_computing_data_reduction        'Platon2001 (Spek, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  nonius-cad4
_diffrn_measurement_method       θ/q2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0226
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            1650
_diffrn_reflns_theta_full        75.07
_diffrn_reflns_theta_max         75.07
_diffrn_reflns_theta_min         3.51
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        5.6
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.233
_exptl_absorpt_correction_T_max  0.8243
_exptl_absorpt_correction_T_min  0.4687
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   Alcock
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.13(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1650
_refine_ls_number_restraints     188
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0463
_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)+(0.0753P)²+0.8116P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1325
_reflns_number_gt                1234
_reflns_number_total             1650
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce41539b.txt
_cod_data_source_block           BRV.LiBr
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Analytical' changed to
'analytical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_Hall     'C 2c 2 '
_cod_original_sg_symbol_H-M      C2221
_cod_database_code               7211222
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x, -y, -z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-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
_atom_site_disorder_assembly
_atom_site_disorder_group
Li1 Li 0.0000 -0.0203(4) -0.2500 0.068(3) Uani 1 2 d SU . .
Br1 Br 0.57786(6) 0.0000 0.0000 0.1174(5) Uani 1 2 d S . .
O1 O 0.1461(3) 0.06811(12) 0.2400(3) 0.0651(7) Uani 1 1 d U . .
O2 O 0.0578(3) 0.02660(13) -0.1217(3) 0.0786(9) Uani 1 1 d U . .
N2 N 0.1021(3) 0.09761(13) 0.0010(4) 0.0619(8) Uani 1 1 d U . .
N1 N 0.3427(3) 0.0384(2) 0.2018(4) 0.0930(15) Uani 1 1 d U . .
H1A H 0.3519 0.0268 0.2766 0.112 Uiso 1 1 calc R . .
H1B H 0.4038 0.0347 0.1487 0.112 Uiso 1 1 calc R . .
C1 C 0.2362(3) 0.06163(18) 0.1691(4) 0.0583(10) Uani 1 1 d U . .
C2 C 0.2303(4) 0.08140(18) 0.0327(4) 0.0605(10) Uani 1 1 d U . .
C3 C 0.0246(4) 0.0681(2) -0.0701(4) 0.0652(10) Uani 1 1 d U . .
C4 C -0.1050(5) 0.0938(2) -0.0725(6) 0.0914(16) Uani 1 1 d U B .
C5 C -0.0842(6) 0.1497(2) -0.0239(6) 0.0994(18) Uani 1 1 d DU . .
C6 C 0.0397(6) 0.1447(2) 0.0500(6) 0.0933(17) Uani 1 1 d U B .
C7 C -0.1738(7) 0.1795(4) 0.0620(8) 0.097(2) Uani 0.64 1 d PDU B 1
C8 C -0.3021(7) 0.1906(4) 0.0018(10) 0.111(3) Uani 0.64 1 d PDU B 1
C9 C -0.3983(9) 0.2116(5) 0.0948(14) 0.127(5) Uani 0.64 1 d PDU B 1
C10 C 0.3312(5) 0.1238(2) 0.0067(7) 0.0903(15) Uani 1 1 d U . .
C11 C 0.3362(8) 0.1389(3) -0.1308(7) 0.122(2) Uani 1 1 d U . .
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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Li Li 0.0008 0.0003 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O2 Li1 O2 103.7(5) 4_554 .
O2 Li1 O1 131.96(15) 4_554 3
O2 Li1 O1 95.54(14) . 3
O2 Li1 O1 95.54(14) 4_554 2_554
O2 Li1 O1 131.96(15) . 2_554
O1 Li1 O1 103.5(5) 3 2_554
C1 O1 Li1 123.6(3) . 2
C3 O2 Li1 139.5(4) . .
C3 N2 C2 122.6(4) . .
C3 N2 C6 113.1(4) . .
C2 N2 C6 124.2(4) . .
C1 N1 H1A 120.0 . .
C1 N1 H1B 120.0 . .
H1A N1 H1B 120.0 . .
O1 C1 N1 123.1(4) . .
O1 C1 C2 121.2(4) . .
N1 C1 C2 115.7(4) . .
N2 C2 C10 113.5(4) . .
N2 C2 C1 110.6(3) . .
C10 C2 C1 111.8(4) . .
N2 C2 H2 106.9 . .
C10 C2 H2 106.9 . .
C1 C2 H2 106.9 . .
O2 C3 N2 124.0(4) . .
O2 C3 C4 127.7(5) . .
N2 C3 C4 108.2(4) . .
C3 C4 C5 105.5(5) . .
C3 C4 H4A 110.6 . .
C5 C4 H4A 110.6 . .
C3 C4 H4B 110.6 . .
C5 C4 H4B 110.6 . .
H4A C4 H4B 108.8 . .
C7 C5 C4 125.6(6) . .
C7 C5 C6 104.2(5) . .
C4 C5 C6 103.0(4) . .
C4 C5 C7' 94.5(7) . .
C6 C5 C7' 130.3(10) . .
C7 C5 H5 107.6 . .
C4 C5 H5 107.6 . .
C6 C5 H5 107.6 . .
C7' C5 H5 110.6 . .
N2 C6 C5 104.9(5) . .
N2 C6 H6C 110.8 . .
C5 C6 H6C 110.8 . .
N2 C6 H6D 110.8 . .
C5 C6 H6D 110.8 . .
H6C C6 H6D 108.8 . .
C8 C7 C5 112.1(5) . .
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 C9 111.6(7) . .
C7 C8 H8A 109.3 . .
C9 C8 H8A 109.3 . .
C7 C8 H8B 109.3 . .
C9 C8 H8B 109.3 . .
H8A C8 H8B 108.0 . .
C8' C7' C5 102.7(11) . .
C8' C7' H71' 111.2 . .
C5 C7' H71' 111.2 . .
C8' C7' H72' 111.2 . .
C5 C7' H72' 111.2 . .
H71' C7' H72' 109.1 . .
C9' C8' C7' 116.5(15) . .
C9' C8' H81' 108.2 . .
C7' C8' H81' 108.2 . .
C9' C8' H82' 108.2 . .
C7' C8' H82' 108.2 . .
H81' C8' H82' 107.3 . .
C8' C9' H91' 109.5 . .
C8' C9' H92' 109.5 . .
H91' C9' H92' 109.5 . .
C8' C9' H93' 109.5 . .
H91' C9' H93' 109.5 . .
H92' C9' H93' 109.5 . .
C2 C10 C11 112.0(5) . .
C2 C10 H10A 109.2 . .
C11 C10 H10A 109.2 . .
C2 C10 H10B 109.2 . .
C11 C10 H10B 109.2 . .
H10A C10 H10B 107.9 . .
C10 C11 H11A 109.5 . .
C10 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C10 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Li1 O2 1.912(7) 4_554
Li1 O2 1.912(7) .
Li1 O1 1.942(7) 3
Li1 O1 1.942(7) 2_554
O1 C1 1.219(5) .
O1 Li1 1.942(7) 2
O2 C3 1.232(5) .
N2 C3 1.337(6) .
N2 C2 1.436(5) .
N2 C6 1.451(6) .
N1 C1 1.302(5) .
N1 H1A 0.8600 .
N1 H1B 0.8600 .
C1 C2 1.549(6) .
C2 C10 1.523(6) .
C2 H2 0.9800 .
C3 C4 1.497(7) .
C4 C5 1.517(8) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C7 1.5105(10) .
C5 C6 1.520(8) .
C5 C7' 1.604(13) .
C5 H5 0.9800 .
C6 H6C 0.9700 .
C6 H6D 0.9700 .
C7 C8 1.5100(10) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C9 1.5102(10) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C7' C8' 1.527(16) .
C7' H71' 0.9700 .
C7' H72' 0.9700 .
C8' C9' 1.526(16) .
C8' H81' 0.9700 .
C8' H82' 0.9700 .
C9' H91' 0.9600 .
C9' H92' 0.9600 .
C9' H93' 0.9600 .
C10 C11 1.527(10) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
