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#$Date: 2016-03-24 01:33:26 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179535 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/04/4500441.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_4500441
loop_
_publ_author_name
'Arlin, Jean-Baptiste'
'Florence, Alastair J.'
'Johnston, Andrea'
'Kennedy, Alan R.'
'Miller, Gary J.'
'Patterson, Kirsty'
_publ_section_title
;
 Systematic Data Set for Structure−Property Investigations:
 Solubility and Solid-State Structure of Alkaline Earth Metal Salts of
 Benzoates
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1318
_journal_paper_doi               10.1021/cg101547r
_journal_volume                  11
_journal_year                    2011
_chemical_formula_sum            'C14 H16 Cl2 Mg O8'
_chemical_formula_weight         407.48
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 91.039(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   39.8060(18)
_cell_length_b                   10.3870(5)
_cell_length_c                   8.8480(4)
_cell_measurement_reflns_used    3928
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     3657.7(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_sigmaI/netI    0.1055
_diffrn_reflns_limit_h_max       51
_diffrn_reflns_limit_h_min       -51
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6930
_diffrn_reflns_theta_full        27.39
_diffrn_reflns_theta_max         27.39
_diffrn_reflns_theta_min         2.03
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.427
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thick needle'
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         4077
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.1489
_refine_ls_R_factor_gt           0.0637
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+11.8016P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.1075
_reflns_number_gt                2280
_reflns_number_total             4077
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cg101547r_si_001.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4500441
loop_
_symmetry_equiv_pos_as_xyz
'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, -y, -z'
'x, -y, 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
Mg1 Mg 0.20061(3) 0.08769(11) -0.01047(12) 0.0210(3) Uani 1 1 d .
Cl2 Cl 0.03417(2) 0.42383(11) -0.13835(13) 0.0501(3) Uani 1 1 d .
Cl1 Cl 0.01476(3) 0.19271(12) 0.46432(13) 0.0578(3) Uani 1 1 d .
O2W O 0.24239(6) 0.0542(2) -0.1359(3) 0.0245(6) Uani 1 1 d .
H3W H 0.2415(10) 0.007(4) -0.195(4) 0.037 Uiso 1 1 d .
H4W H 0.2638(9) 0.043(3) -0.081(4) 0.037 Uiso 1 1 d .
O2 O 0.16395(5) 0.1269(2) 0.1397(2) 0.0230(5) Uani 1 1 d .
O3 O 0.19835(5) 0.2713(2) -0.1003(2) 0.0257(6) Uani 1 1 d .
O1 O 0.16973(5) -0.0225(2) 0.3195(2) 0.0274(6) Uani 1 1 d .
O4 O 0.19911(6) 0.4709(2) -0.0101(3) 0.0401(7) Uani 1 1 d .
C8 C 0.18365(9) 0.3757(4) -0.0631(4) 0.0282(9) Uani 1 1 d .
C2 C 0.11911(8) 0.0993(3) 0.3075(3) 0.0225(8) Uani 1 1 d .
C3 C 0.10044(9) 0.1971(3) 0.2393(4) 0.0278(8) Uani 1 1 d .
H13 H 0.1100 0.2457 0.1600 0.033 Uiso 1 1 calc R
C13 C 0.09375(9) 0.3086(4) -0.1875(4) 0.0315(9) Uani 1 1 d .
H14 H 0.0814 0.2482 -0.2472 0.038 Uiso 1 1 calc R
C7 C 0.10477(8) 0.0301(4) 0.4253(4) 0.0266(8) Uani 1 1 d .
H15 H 0.1173 -0.0365 0.4737 0.032 Uiso 1 1 calc R
C5 C 0.05479(9) 0.1555(4) 0.4025(4) 0.0339(9) Uani 1 1 d .
C1 C 0.15346(8) 0.0657(3) 0.2529(3) 0.0215(8) Uani 1 1 d .
C14 C 0.12831(8) 0.2974(3) -0.1705(4) 0.0261(8) Uani 1 1 d .
H18 H 0.1397 0.2288 -0.2185 0.031 Uiso 1 1 calc R
C6 C 0.07250(9) 0.0574(4) 0.4726(4) 0.0329(9) Uani 1 1 d .
H19 H 0.0628 0.0093 0.5519 0.039 Uiso 1 1 calc R
C9 C 0.14640(8) 0.3861(3) -0.0835(4) 0.0238(8) Uani 1 1 d .
C10 C 0.12930(9) 0.4844(4) -0.0120(4) 0.0304(9) Uani 1 1 d .
H21 H 0.1414 0.5447 0.0485 0.037 Uiso 1 1 calc R
C11 C 0.09466(9) 0.4956(4) -0.0278(4) 0.0330(9) Uani 1 1 d .
H22 H 0.0831 0.5628 0.0222 0.040 Uiso 1 1 calc R
C12 C 0.07733(8) 0.4089(4) -0.1163(4) 0.0298(9) Uani 1 1 d .
C4 C 0.06814(9) 0.2249(4) 0.2850(4) 0.0347(9) Uani 1 1 d .
H25 H 0.0554 0.2907 0.2362 0.042 Uiso 1 1 calc R
O3W O 0.23586(6) 0.1526(3) 0.1585(3) 0.0259(6) Uani 1 1 d .
H5W H 0.2550(9) 0.175(4) 0.140(4) 0.039 Uiso 1 1 d .
H6W H 0.2277(9) 0.206(4) 0.215(4) 0.039 Uiso 1 1 d .
O1W O 0.20408(7) -0.1031(3) 0.0680(3) 0.0328(7) Uani 1 1 d .
H1W H 0.1942(9) -0.111(4) 0.151(4) 0.049 Uiso 1 1 d .
H2W H 0.2042(10) -0.161(4) 0.020(5) 0.049 Uiso 1 1 d .
O29 O 0.27453(12) 0.7965(5) 0.0931(5) 0.0243(11) Uiso 0.50 1 d P
H28W H 0.2540(17) 0.825(7) 0.086(7) 0.036 Uiso 0.50 1 d P
O28 O 0.30656(13) 0.7986(5) 0.1391(6) 0.0287(12) Uiso 0.50 1 d P
H29W H 0.2947(10) 0.851(4) 0.107(4) 0.043 Uiso 1 1 d .
H30W H 0.3263(18) 0.794(7) 0.189(8) 0.043 Uiso 0.50 1 d P
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mg Mg 0.0486 0.0363 '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 Mg1 O1 96.81(9) . 6
O2 Mg1 O2W 171.50(11) . .
O1 Mg1 O2W 91.62(10) 6 .
O2 Mg1 O3 92.29(10) . .
O1 Mg1 O3 90.06(10) 6 .
O2W Mg1 O3 88.75(10) . .
O2 Mg1 O1W 90.96(11) . .
O1 Mg1 O1W 88.04(11) 6 .
O2W Mg1 O1W 88.26(11) . .
O3 Mg1 O1W 176.42(11) . .
O2 Mg1 O3W 87.10(10) . .
O1 Mg1 O3W 176.08(11) 6 .
O2W Mg1 O3W 84.46(10) . .
O3 Mg1 O3W 90.09(10) . .
O1W Mg1 O3W 91.60(11) . .
Mg1 O2W H3W 119(3) . .
Mg1 O2W H4W 117.5(19) . .
H3W O2W H4W 108(4) . .
C1 O2 Mg1 132.0(2) . .
C8 O3 Mg1 134.5(2) . .
C1 O1 Mg1 151.9(2) . 6_556
O4 C8 O3 122.9(3) . .
O4 C8 C9 117.9(4) . .
O3 C8 C9 119.2(3) . .
C3 C2 C7 118.5(3) . .
C3 C2 C1 120.9(3) . .
C7 C2 C1 120.6(3) . .
C4 C3 C2 121.2(3) . .
C4 C3 H13 119.4 . .
C2 C3 H13 119.4 . .
C14 C13 C12 119.2(3) . .
C14 C13 H14 120.4 . .
C12 C13 H14 120.4 . .
C6 C7 C2 120.9(3) . .
C6 C7 H15 119.6 . .
C2 C7 H15 119.6 . .
C6 C5 C4 121.6(3) . .
C6 C5 Cl1 119.1(3) . .
C4 C5 Cl1 119.3(3) . .
O1 C1 O2 124.1(3) . .
O1 C1 C2 118.8(3) . .
O2 C1 C2 117.1(3) . .
C13 C14 C9 120.5(3) . .
C13 C14 H18 119.8 . .
C9 C14 H18 119.8 . .
C5 C6 C7 118.9(3) . .
C5 C6 H19 120.5 . .
C7 C6 H19 120.5 . .
C10 C9 C14 119.1(3) . .
C10 C9 C8 119.5(3) . .
C14 C9 C8 121.4(3) . .
C9 C10 C11 120.7(3) . .
C9 C10 H21 119.6 . .
C11 C10 H21 119.6 . .
C12 C11 C10 119.4(4) . .
C12 C11 H22 120.3 . .
C10 C11 H22 120.3 . .
C11 C12 C13 121.1(3) . .
C11 C12 Cl2 119.5(3) . .
C13 C12 Cl2 119.4(3) . .
C5 C4 C3 118.9(3) . .
C5 C4 H25 120.5 . .
C3 C4 H25 120.5 . .
Mg1 O3W H5W 123(3) . .
Mg1 O3W H6W 112(3) . .
H5W O3W H6W 108(4) . .
Mg1 O1W H1W 111(3) . .
Mg1 O1W H2W 125(3) . .
H1W O1W H2W 116(4) . .
O28 O29 H28W 155(4) . .
O28 O29 H29W 35(2) . .
H28W O29 H29W 125(5) . .
O29 O28 H29W 47(3) . .
O29 O28 H30W 168(4) . .
H29W O28 H30W 138(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mg1 O2 2.032(2) .
Mg1 O1 2.041(2) 6
Mg1 O2W 2.046(3) .
Mg1 O3 2.068(3) .
Mg1 O1W 2.104(3) .
Mg1 O3W 2.141(3) .
Cl2 C12 1.733(3) .
Cl1 C5 1.737(4) .
O2W H3W 0.72(4) .
O2W H4W 0.98(4) .
O2 C1 1.264(4) .
O3 C8 1.278(4) .
O1 C1 1.262(4) .
O1 Mg1 2.041(2) 6_556
O4 C8 1.252(4) .
C8 C9 1.494(5) .
C2 C3 1.390(5) .
C2 C7 1.396(4) .
C2 C1 1.500(4) .
C3 C4 1.385(5) .
C3 H13 0.9500 .
C13 C14 1.386(4) .
C13 C12 1.388(5) .
C13 H14 0.9500 .
C7 C6 1.388(4) .
C7 H15 0.9500 .
C5 C6 1.380(5) .
C5 C4 1.380(5) .
C14 C9 1.393(5) .
C14 H18 0.9500 .
C6 H19 0.9500 .
C9 C10 1.386(5) .
C10 C11 1.388(5) .
C10 H21 0.9500 .
C11 C12 1.371(5) .
C11 H22 0.9500 .
C4 H25 0.9500 .
O3W H5W 0.82(4) .
O3W H6W 0.82(4) .
O1W H1W 0.85(4) .
O1W H2W 0.74(4) .
O29 O28 1.332(7) .
O29 H28W 0.87(7) .
O29 H29W 0.99(4) .
O28 H29W 0.77(4) .
O28 H30W 0.90(7) .
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_1
O1 Mg1 O2 C1 100.5(3) 6
O2W Mg1 O2 C1 -72.3(9) .
O3 Mg1 O2 C1 -169.2(3) .
O1W Mg1 O2 C1 12.4(3) .
O3W Mg1 O2 C1 -79.2(3) .
O2 Mg1 O3 C8 9.3(3) .
O1 Mg1 O3 C8 106.1(3) 6
O2W Mg1 O3 C8 -162.3(3) .
O1W Mg1 O3 C8 164.1(17) .
O3W Mg1 O3 C8 -77.8(3) .
Mg1 O3 C8 O4 108.2(4) .
Mg1 O3 C8 C9 -72.0(4) .
C7 C2 C3 C4 -0.9(5) .
C1 C2 C3 C4 177.2(3) .
C3 C2 C7 C6 0.6(5) .
C1 C2 C7 C6 -177.5(3) .
Mg1 O1 C1 O2 97.8(5) 6_556
Mg1 O1 C1 C2 -83.7(5) 6_556
Mg1 O2 C1 O1 18.4(5) .
Mg1 O2 C1 C2 -160.1(2) .
C3 C2 C1 O1 179.0(3) .
C7 C2 C1 O1 -3.0(5) .
C3 C2 C1 O2 -2.4(5) .
C7 C2 C1 O2 175.6(3) .
C12 C13 C14 C9 -0.3(5) .
C4 C5 C6 C7 1.4(6) .
Cl1 C5 C6 C7 -178.4(3) .
C2 C7 C6 C5 -0.8(5) .
C13 C14 C9 C10 1.1(5) .
C13 C14 C9 C8 179.8(3) .
O4 C8 C9 C10 -15.4(5) .
O3 C8 C9 C10 164.8(3) .
O4 C8 C9 C14 166.0(3) .
O3 C8 C9 C14 -13.9(5) .
C14 C9 C10 C11 -0.7(5) .
C8 C9 C10 C11 -179.4(3) .
C9 C10 C11 C12 -0.5(5) .
C10 C11 C12 C13 1.4(5) .
C10 C11 C12 Cl2 -179.2(3) .
C14 C13 C12 C11 -1.0(5) .
C14 C13 C12 Cl2 179.6(3) .
C6 C5 C4 C3 -1.7(6) .
Cl1 C5 C4 C3 178.2(3) .
C2 C3 C4 C5 1.4(5) .
