#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/69/2216955.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_2216955
loop_
_publ_author_name
'Martins, Nuno D.'
'Silva, Joana A.'
'Ramos Silva, Manuela'
'Matos Beja, Ana'
'Sobral, Abilio J.F.N.'
_publ_section_title
;(Benzoato-κ²O,O')(quinoline-2-carboxylato-κ²N,O)(quinoline-2-carboxylic
 acid-κ²N,O)manganese(II)
;
_journal_coeditor_code           BT2660
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m258
_journal_page_last               m258
_journal_paper_doi               10.1107/S1600536807066809
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Mn (C7 H5 O2) (C10 H6 N O2) (C10 H7 N O2)]'
_chemical_formula_sum            'C27 H18 Mn N2 O6'
_chemical_formula_weight         521.37
_chemical_name_systematic
;
(Benzoato-κ²O,O')(quinoline-2-carboxylato-κ²N,O)(quinoline-2-carboxylic
acid-κ²N,O)manganese(II)
;
_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                 117.2880(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.3839(4)
_cell_length_b                   11.6775(2)
_cell_length_c                   11.6306(2)
_cell_measurement_reflns_used    8901
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.37
_cell_volume                     2339.67(8)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0156
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            25798
_diffrn_reflns_theta_full        28.40
_diffrn_reflns_theta_max         28.40
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_T_max  0.908
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS;  Sheldrick, 2000)'
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1068
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.684
_refine_diff_density_min         -0.498
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2917
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0481
_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)+(0.0806P)²+2.8119P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1494
_reflns_number_gt                2413
_reflns_number_total             2917
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2660.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2216955
_cod_database_fobs_code          2216955
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_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
Mn Mn1 0.5000 0.20556(4) 0.2500 0.03799(18) Uani d S 1
O O1 0.48852(12) 0.37094(15) 0.14858(17) 0.0505(4) Uani d . 1
O O2 0.48495(10) 0.09330(17) 0.09597(18) 0.0508(5) Uani d D 1
H H2 0.525(3) 0.041(5) 0.103(7) 0.07(2) Uiso d PD 0.50
N N1 0.37188(11) 0.15467(17) 0.15100(18) 0.0378(4) Uani d . 1
C C1 0.5000 0.4239(3) 0.2500 0.0395(7) Uani d S 1
C C2 0.5000 0.5526(3) 0.2500 0.0359(6) Uani d S 1
C C3 0.48852(16) 0.6123(2) 0.1396(2) 0.0457(6) Uani d . 1
H H3 0.4807 0.5728 0.0652 0.055 Uiso calc R 1
C C4 0.4888(2) 0.7302(3) 0.1403(3) 0.0569(7) Uani d . 1
H H4 0.4813 0.7702 0.0664 0.068 Uiso calc R 1
C C5 0.5000 0.7889(3) 0.2500 0.0582(10) Uani d S 1
H H5 0.5000 0.8685 0.2500 0.070 Uiso calc SR 1
C C6 0.41618(15) 0.0511(3) 0.0173(3) 0.0521(6) Uani d . 1
O O3 0.39792(16) 0.0125(4) -0.0885(3) 0.1252(15) Uani d . 1
C C7 0.35213(13) 0.0869(2) 0.0500(2) 0.0402(5) Uani d . 1
C C15 0.31580(14) 0.1843(2) 0.1866(2) 0.0418(5) Uani d . 1
C C10 0.23875(14) 0.1435(2) 0.1169(3) 0.0487(6) Uani d . 1
C C9 0.22055(15) 0.0739(3) 0.0085(3) 0.0553(7) Uani d . 1
H H9 0.1701 0.0476 -0.0404 0.066 Uiso calc R 1
C C8 0.27651(15) 0.0452(2) -0.0249(3) 0.0501(6) Uani d . 1
H H8 0.2652 -0.0014 -0.0963 0.060 Uiso calc R 1
C C11 0.18377(18) 0.1752(3) 0.1597(4) 0.0668(9) Uani d . 1
H H11 0.1327 0.1500 0.1148 0.080 Uiso calc R 1
C C12 0.2053(2) 0.2419(4) 0.2655(4) 0.0790(11) Uani d . 1
H H12 0.1690 0.2608 0.2938 0.095 Uiso calc R 1
C C13 0.2808(2) 0.2828(3) 0.3327(3) 0.0710(9) Uani d . 1
H H13 0.2942 0.3292 0.4049 0.085 Uiso calc R 1
C C14 0.33583(17) 0.2557(3) 0.2942(3) 0.0551(7) Uani d . 1
H H14 0.3860 0.2844 0.3389 0.066 Uiso calc R 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'
Mn Mn 0.3368 0.7283 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O2 Mn1 O2 2_655 . 104.00(12)
O2 Mn1 O1 2_655 2_655 98.44(7)
O2 Mn1 O1 . 2_655 157.55(8)
O2 Mn1 O1 2_655 . 157.55(8)
O2 Mn1 O1 . . 98.44(7)
O1 Mn1 O1 2_655 . 59.13(9)
O2 Mn1 N1 2_655 . 87.81(7)
O2 Mn1 N1 . . 73.62(7)
O1 Mn1 N1 2_655 . 108.35(7)
O1 Mn1 N1 . . 97.90(7)
O2 Mn1 N1 2_655 2_655 73.62(7)
O2 Mn1 N1 . 2_655 87.81(7)
O1 Mn1 N1 2_655 2_655 97.90(7)
O1 Mn1 N1 . 2_655 108.35(7)
N1 Mn1 N1 . 2_655 149.86(10)
O2 Mn1 C1 2_655 . 128.00(6)
O2 Mn1 C1 . . 128.00(6)
O1 Mn1 C1 2_655 . 29.57(4)
O1 Mn1 C1 . . 29.57(5)
N1 Mn1 C1 . . 105.07(5)
N1 Mn1 C1 2_655 . 105.07(5)
C1 O1 Mn1 . . 89.89(16)
C6 O2 Mn1 . . 121.28(15)
C6 O2 H2 . . 110(4)
Mn1 O2 H2 . . 122(4)
C7 N1 C15 . . 118.2(2)
C7 N1 Mn1 . . 114.17(15)
C15 N1 Mn1 . . 127.58(16)
O1 C1 O1 . 2_655 121.1(3)
O1 C1 C2 . . 119.46(16)
O1 C1 C2 2_655 . 119.46(16)
O1 C1 Mn1 . . 60.54(16)
O1 C1 Mn1 2_655 . 60.54(16)
C2 C1 Mn1 . . 180.0
C3 C2 C3 . 2_655 119.6(3)
C3 C2 C1 . . 120.20(16)
C3 C2 C1 2_655 . 120.20(16)
C4 C3 C2 . . 119.9(2)
C4 C3 H3 . . 120.0
C2 C3 H3 . . 120.0
C5 C4 C3 . . 120.2(3)
C5 C4 H4 . . 119.9
C3 C4 H4 . . 119.9
C4 C5 C4 . 2_655 120.2(4)
C4 C5 H5 . . 119.9
C4 C5 H5 2_655 . 119.9
O3 C6 O2 . . 125.5(3)
O3 C6 C7 . . 118.1(2)
O2 C6 C7 . . 114.0(2)
N1 C7 C8 . . 123.7(2)
N1 C7 C6 . . 116.9(2)
C8 C7 C6 . . 119.3(2)
N1 C15 C14 . . 119.0(2)
N1 C15 C10 . . 121.0(2)
C14 C15 C10 . . 119.9(2)
C9 C10 C15 . . 118.3(2)
C9 C10 C11 . . 123.2(3)
C15 C10 C11 . . 118.5(3)
C8 C9 C10 . . 119.9(2)
C8 C9 H9 . . 120.1
C10 C9 H9 . . 120.1
C9 C8 C7 . . 118.8(3)
C9 C8 H8 . . 120.6
C7 C8 H8 . . 120.6
C12 C11 C10 . . 120.1(3)
C12 C11 H11 . . 119.9
C10 C11 H11 . . 119.9
C11 C12 C13 . . 121.2(3)
C11 C12 H12 . . 119.4
C13 C12 H12 . . 119.4
C14 C13 C12 . . 120.8(3)
C14 C13 H13 . . 119.6
C12 C13 H13 . . 119.6
C13 C14 C15 . . 119.4(3)
C13 C14 H14 . . 120.3
C15 C14 H14 . . 120.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Mn1 O2 2_655 2.1293(18)
Mn1 O2 . 2.1293(18)
Mn1 O1 2_655 2.2203(19)
Mn1 O1 . 2.2203(19)
Mn1 N1 . 2.2858(19)
Mn1 N1 2_655 2.2858(19)
Mn1 C1 . 2.550(3)
O1 C1 . 1.258(2)
O2 C6 . 1.319(3)
O2 H2 . 0.959(10)
N1 C7 . 1.319(3)
N1 C15 . 1.373(3)
C1 O1 2_655 1.258(2)
C1 C2 . 1.503(5)
C2 C3 . 1.386(3)
C2 C3 2_655 1.386(3)
C3 C4 . 1.377(4)
C3 H3 . 0.9300
C4 C5 . 1.375(3)
C4 H4 . 0.9300
C5 C4 2_655 1.375(3)
C5 H5 . 0.9300
C6 O3 . 1.200(4)
C6 C7 . 1.515(3)
C7 C8 . 1.405(3)
C15 C14 . 1.401(4)
C15 C10 . 1.416(4)
C10 C9 . 1.403(4)
C10 C11 . 1.416(4)
C9 C8 . 1.352(4)
C9 H9 . 0.9300
C8 H8 . 0.9300
C11 C12 . 1.350(6)
C11 H11 . 0.9300
C12 C13 . 1.390(6)
C12 H12 . 0.9300
C13 C14 . 1.370(4)
C13 H13 . 0.9300
C14 H14 . 0.9300
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
O2 H2 O3 5_655 0.96(7) 1.70(7) 2.621(4) 160(6)
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_site_symmetry_4
_geom_torsion
O2 Mn1 O1 C1 2_655 . 3.1(2)
O2 Mn1 O1 C1 . . -178.80(10)
O1 Mn1 O1 C1 2_655 . 0.0
N1 Mn1 O1 C1 . . 106.70(10)
N1 Mn1 O1 C1 2_655 . -88.30(11)
O2 Mn1 O2 C6 2_655 . 85.4(2)
O1 Mn1 O2 C6 2_655 . -96.5(3)
O1 Mn1 O2 C6 . . -93.8(2)
N1 Mn1 O2 C6 . . 2.0(2)
N1 Mn1 O2 C6 2_655 . 157.9(2)
C1 Mn1 O2 C6 . . -94.6(2)
O2 Mn1 N1 C7 2_655 . -107.04(17)
O2 Mn1 N1 C7 . . -1.76(16)
O1 Mn1 N1 C7 2_655 . 154.79(16)
O1 Mn1 N1 C7 . . 94.77(17)
N1 Mn1 N1 C7 2_655 . -55.92(15)
C1 Mn1 N1 C7 . . 124.07(15)
O2 Mn1 N1 C15 2_655 . 71.34(19)
O2 Mn1 N1 C15 . . 176.6(2)
O1 Mn1 N1 C15 2_655 . -26.8(2)
O1 Mn1 N1 C15 . . -86.85(19)
N1 Mn1 N1 C15 2_655 . 122.46(19)
C1 Mn1 N1 C15 . . -57.55(19)
Mn1 O1 C1 O1 . 2_655 0.0000(10)
Mn1 O1 C1 C2 . . 180.0
O2 Mn1 C1 O1 2_655 . -178.49(12)
O2 Mn1 C1 O1 . . 1.51(12)
O1 Mn1 C1 O1 2_655 . 180.0
N1 Mn1 C1 O1 . . -79.27(12)
N1 Mn1 C1 O1 2_655 . 100.73(12)
O2 Mn1 C1 O1 2_655 2_655 1.51(12)
O2 Mn1 C1 O1 . 2_655 -178.49(12)
O1 Mn1 C1 O1 . 2_655 180.0000(10)
N1 Mn1 C1 O1 . 2_655 100.73(12)
N1 Mn1 C1 O1 2_655 2_655 -79.27(12)
O2 Mn1 C1 C2 2_655 . -7E1(10)
O2 Mn1 C1 C2 . . 11E1(10)
O1 Mn1 C1 C2 2_655 . -7E1(10)
O1 Mn1 C1 C2 . . 11E1(10)
N1 Mn1 C1 C2 . . 3E1(10)
N1 Mn1 C1 C2 2_655 . -15E1(10)
O1 C1 C2 C3 . . -0.90(17)
O1 C1 C2 C3 2_655 . 179.10(17)
Mn1 C1 C2 C3 . . -11E1(10)
O1 C1 C2 C3 . 2_655 179.10(17)
O1 C1 C2 C3 2_655 2_655 -0.90(17)
Mn1 C1 C2 C3 . 2_655 7E1(10)
C3 C2 C3 C4 2_655 . 0.2(2)
C1 C2 C3 C4 . . -179.8(2)
C2 C3 C4 C5 . . -0.3(4)
C3 C4 C5 C4 . 2_655 0.2(2)
Mn1 O2 C6 O3 . . 160.0(3)
Mn1 O2 C6 C7 . . -1.8(3)
C15 N1 C7 C8 . . 1.4(4)
Mn1 N1 C7 C8 . . 179.9(2)
C15 N1 C7 C6 . . -177.1(2)
Mn1 N1 C7 C6 . . 1.5(3)
O3 C6 C7 N1 . . -163.2(3)
O2 C6 C7 N1 . . 0.1(4)
O3 C6 C7 C8 . . 18.3(5)
O2 C6 C7 C8 . . -178.5(2)
C7 N1 C15 C14 . . 179.6(2)
Mn1 N1 C15 C14 . . 1.3(3)
C7 N1 C15 C10 . . -0.1(3)
Mn1 N1 C15 C10 . . -178.43(17)
N1 C15 C10 C9 . . -1.4(4)
C14 C15 C10 C9 . . 178.9(3)
N1 C15 C10 C11 . . 178.8(2)
C14 C15 C10 C11 . . -0.9(4)
C15 C10 C9 C8 . . 1.7(4)
C11 C10 C9 C8 . . -178.6(3)
C10 C9 C8 C7 . . -0.5(4)
N1 C7 C8 C9 . . -1.1(4)
C6 C7 C8 C9 . . 177.3(3)
C9 C10 C11 C12 . . 179.6(3)
C15 C10 C11 C12 . . -0.7(5)
C10 C11 C12 C13 . . 1.4(6)
C11 C12 C13 C14 . . -0.6(6)
C12 C13 C14 C15 . . -1.0(5)
N1 C15 C14 C13 . . -178.0(3)
C10 C15 C14 C13 . . 1.7(4)
