#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/30/2233046.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_2233046
loop_
_publ_author_name
'Maccaroni, Elisabetta'
'Panzeri, Walter'
'Malpezzi, Luciana'
_publ_section_title
;
 Calcium acamprosate: a triclinic polymorph
;
_journal_coeditor_code           ZL2412
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1736
_journal_page_last               m1737
_journal_paper_doi               10.1107/S1600536811046940
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Ca (C5 H10 N O4 S)2]'
_chemical_formula_moiety         'C10 H20 Ca1 N2 O8 S2'
_chemical_formula_sum            'C10 H20 Ca N2 O8 S2'
_chemical_formula_weight         400.48
_chemical_name_common            'calcium acamprosate  form B'
_chemical_name_systematic
;
poly[bis(μ₃-4-acetamidopropanesulfonato)calcium]
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                69.1590(10)
_cell_angle_beta                 84.305(2)
_cell_angle_gamma                89.329(2)
_cell_formula_units_Z            1
_cell_length_a                   5.5372(4)
_cell_length_b                   8.1487(6)
_cell_length_c                   9.7578(7)
_cell_measurement_reflns_used    4793
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.1
_cell_measurement_theta_min      2.33
_cell_volume                     409.31(5)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL/NT (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            22542
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  0.9477
_exptl_absorpt_correction_T_min  0.8273
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(TWINABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.625
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             210
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.333
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         8721
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0339
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0478P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0877
_reflns_number_gt                7647
_reflns_number_total             8721
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            zl2412.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C10 H20 Ca1 N2 O8 S2'
_cod_database_code               2233046
_cod_database_fobs_code          2233046
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Ca Ca 1.0000 0.5000 0.0000 0.02008(8) Uani d S 1 2
S S 0.46696(4) 0.53055(3) 0.23925(3) 0.02053(7) Uani d . 1 1
O O1 0.39518(14) 0.65813(9) 0.30610(8) 0.03333(19) Uani d . 1 1
O O2 0.71997(12) 0.55429(9) 0.17559(8) 0.02862(18) Uani d . 1 1
O O3 0.30448(15) 0.52304(11) 0.13414(8) 0.0383(2) Uani d . 1 1
O O4 0.06178(14) -0.20198(9) 0.83520(8) 0.0340(2) Uani d . 1 1
N N -0.01015(17) 0.07771(11) 0.69942(10) 0.0334(2) Uani d . 1 1
H H1N -0.1087 0.1630 0.6866 0.040 Uiso calc R 1 1
C C1 0.44992(19) 0.32245(13) 0.38187(11) 0.0257(2) Uani d . 1 1
H H1A 0.4796 0.2327 0.3388 0.031 Uiso calc R 1 1
H H1B 0.5769 0.3165 0.4450 0.031 Uiso calc R 1 1
C C2 0.20568(19) 0.28297(13) 0.47557(12) 0.0282(2) Uani d . 1 1
H H2A 0.1742 0.3719 0.5193 0.034 Uiso calc R 1 1
H H2B 0.0776 0.2860 0.4138 0.034 Uiso calc R 1 1
C C3 0.20577(19) 0.10418(14) 0.59580(12) 0.0305(3) Uani d . 1 1
H H3A 0.2108 0.0138 0.5524 0.037 Uiso calc R 1 1
H H3B 0.3493 0.0946 0.6474 0.037 Uiso calc R 1 1
C C4 -0.0642(2) -0.07020(14) 0.81257(12) 0.0294(3) Uani d . 1 1
C C5 -0.2877(2) -0.07026(17) 0.91136(14) 0.0541(4) Uani d . 1 1
H H5A -0.2469 -0.0998 1.0105 0.081 Uiso calc R 1 1
H H5B -0.4034 -0.1553 0.9080 0.081 Uiso calc R 1 1
H H5C -0.3566 0.0442 0.8791 0.081 Uiso calc R 1 1
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'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ca Ca 0.2262 0.3064 '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_site_symmetry_3
_geom_angle
O3 Ca O3 2_665 1_655 180.00(4)
O3 Ca O2 2_665 2_765 88.69(3)
O3 Ca O2 1_655 2_765 91.31(3)
O3 Ca O2 2_665 . 91.31(3)
O3 Ca O2 1_655 . 88.69(3)
O2 Ca O2 2_765 . 180.0000(10)
O3 Ca O4 2_665 2_656 92.36(3)
O3 Ca O4 1_655 2_656 87.64(3)
O2 Ca O4 2_765 2_656 97.35(3)
O2 Ca O4 . 2_656 82.65(3)
O3 Ca O4 2_665 1_664 87.64(3)
O3 Ca O4 1_655 1_664 92.36(3)
O2 Ca O4 2_765 1_664 82.65(3)
O2 Ca O4 . 1_664 97.35(3)
O4 Ca O4 2_656 1_664 180.00(2)
O1 S O3 . . 112.42(5)
O1 S O2 . . 112.71(5)
O3 S O2 . . 111.72(5)
O1 S C1 . . 107.12(5)
O3 S C1 . . 106.99(5)
O2 S C1 . . 105.35(5)
S O2 Ca . . 144.39(5)
S O3 Ca . 1_455 170.63(5)
C4 O4 Ca . 1_446 132.62(7)
C4 N C3 . . 123.86(9)
C4 N H1N . . 118.1
C3 N H1N . . 118.1
C2 C1 S . . 113.33(7)
C2 C1 H1A . . 108.9
S C1 H1A . . 108.9
C2 C1 H1B . . 108.9
S C1 H1B . . 108.9
H1A C1 H1B . . 107.7
C3 C2 C1 . . 110.28(8)
C3 C2 H2A . . 109.6
C1 C2 H2A . . 109.6
C3 C2 H2B . . 109.6
C1 C2 H2B . . 109.6
H2A C2 H2B . . 108.1
N C3 C2 . . 110.46(8)
N C3 H3A . . 109.6
C2 C3 H3A . . 109.6
N C3 H3B . . 109.6
C2 C3 H3B . . 109.6
H3A C3 H3B . . 108.1
O4 C4 N . . 122.27(10)
O4 C4 C5 . . 121.44(10)
N C4 C5 . . 116.28(9)
C4 C5 H5A . . 109.5
C4 C5 H5B . . 109.5
H5A C5 H5B . . 109.5
C4 C5 H5C . . 109.5
H5A C5 H5C . . 109.5
H5B C5 H5C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Ca O3 2_665 2.2828(8)
Ca O3 1_655 2.2828(8)
Ca O2 2_765 2.3519(7)
Ca O2 . 2.3519(7)
Ca O4 2_656 2.3941(7)
Ca O4 1_664 2.3941(7)
S O1 . 1.4442(7)
S O3 . 1.4471(8)
S O2 . 1.4609(7)
S C1 . 1.7662(10)
O3 Ca 1_455 2.2828(8)
O4 C4 . 1.2382(12)
O4 Ca 1_446 2.3941(7)
N C4 . 1.3256(13)
N C3 . 1.4523(13)
N H1N . 0.8600
C1 C2 . 1.5245(13)
C1 H1A . 0.9700
C1 H1B . 0.9700
C2 C3 . 1.5109(14)
C2 H2A . 0.9700
C2 H2B . 0.9700
C3 H3A . 0.9700
C3 H3B . 0.9700
C4 C5 . 1.4910(16)
C5 H5A . 0.9600
C5 H5B . 0.9600
C5 H5C . 0.9600
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
_geom_hbond_publ_flag
N H1N O1 2_566 0.86 2.15 3.0025(12) 168.6 yes
C5 H5C O1 2_566 0.96 2.48 3.3569(15) 152.2 yes
C1 H1B O1 2_666 0.97 2.53 3.3007(14) 136.5 yes
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
O1 S O2 Ca . -156.68(7)
O3 S O2 Ca . -28.97(9)
C1 S O2 Ca . 86.85(8)
O3 Ca O2 S 2_665 23.48(8)
O3 Ca O2 S 1_655 -156.52(8)
O4 Ca O2 S 2_656 -68.73(8)
O4 Ca O2 S 1_664 111.27(8)
O1 S C1 C2 . 52.32(9)
O3 S C1 C2 . -68.44(9)
O2 S C1 C2 . 172.54(8)
S C1 C2 C3 . -179.41(8)
C4 N C3 C2 . 176.87(11)
C1 C2 C3 N . 170.74(9)
Ca O4 C4 N 1_446 -169.56(8)
Ca O4 C4 C5 1_446 9.90(18)
C3 N C4 O4 . -3.33(19)
C3 N C4 C5 . 177.18(11)
