#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/84/2018488.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_2018488
loop_
_publ_author_name
'Jin, Shuang'
'Wen, Mei-Feng'
'Liu, Lu-Fang'
'Gao, Ming-Juan'
'Wu, Jian-Zhong'
_publ_section_title
;
 Synthesis and supramolecular networks of
 5,6-dioxo-1,10-phenanthroline-2,9-dicarboxylic acid dihydrate and its
 first coordination compound
 cis-diaquachlorido(5,6-dioxo-1,10-phenanthroline-2,9-dicarboxylic
 acid-κ⁴O²,N,N',O⁹)manganese(II)
 chloride dihydrate
;
_journal_coeditor_code           TP3010
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m135
_journal_page_last               m138
_journal_paper_doi               10.1107/S0108270112017763
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '[Mn Cl (C14 H6 N2 O6) (H2 O1)2] Cl, 2H2 O'
_chemical_formula_moiety         'C14 H10 Cl Mn N2 O8 +, Cl -, 2(H2 O)'
_chemical_formula_sum            'C14 H14 Cl2 Mn N2 O10'
_chemical_formula_weight         496.11
_chemical_name_systematic
;
cis-diaquachlorido(5,6-dioxo-1,10-phenanthroline-2,9-dicarboxylic
acid-κ⁴O²,N,N',O⁹)manganese(II) chloride
dihydrate
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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            8
_cell_length_a                   17.195(6)
_cell_length_b                   12.411(5)
_cell_length_c                   17.569(6)
_cell_measurement_reflns_used    2414
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.54
_cell_measurement_theta_min      2.32
_cell_volume                     3749(2)
_computing_cell_refinement       'APEX2 (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'APEX2 (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω 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  0.0815
_diffrn_reflns_av_sigmaI/netI    0.0609
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17437
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    1.048
_exptl_absorpt_correction_T_max  0.7440
_exptl_absorpt_correction_T_min  0.6674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2008
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.325
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3372
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0455
_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)+(0.0578P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1214
_reflns_number_gt                2021
_reflns_number_total             3372
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tp3010.cif
_cod_data_source_block           II
_cod_original_cell_volume        3750(2)
_cod_database_code               2018488
_cod_database_fobs_code          2018488
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, 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
C C1 0.5332(2) 0.1261(3) 0.4605(2) 0.0298(9) Uani d . 1 1
C C2 0.6055(2) 0.1135(3) 0.5084(2) 0.0293(9) Uani d . 1 1
C C3 0.6061(2) 0.1024(3) 0.5866(2) 0.0351(10) Uani d . 1 1
H H3 0.5598 0.0990 0.6140 0.042 Uiso calc R 1 1
C C4 0.6777(2) 0.0963(3) 0.6236(2) 0.0341(10) Uani d . 1 1
H H4 0.6800 0.0887 0.6762 0.041 Uiso calc R 1 1
C C5 0.7457(2) 0.1018(3) 0.5810(2) 0.0305(9) Uani d . 1 1
C C6 0.7396(2) 0.1113(3) 0.5021(2) 0.0260(9) Uani d . 1 1
C C7 0.8248(2) 0.0974(3) 0.6183(2) 0.0356(10) Uani d . 1 1
C C8 0.8972(2) 0.1048(3) 0.5651(2) 0.0362(10) Uani d . 1 1
C C9 0.8851(2) 0.1166(3) 0.4818(2) 0.0292(9) Uani d . 1 1
C C10 0.8087(2) 0.1196(3) 0.4520(2) 0.0270(9) Uani d . 1 1
C C11 0.9467(2) 0.1244(3) 0.4305(2) 0.0376(10) Uani d . 1 1
H H11 0.9978 0.1225 0.4479 0.045 Uiso calc R 1 1
C C12 0.9315(2) 0.1349(3) 0.3534(2) 0.0407(11) Uani d . 1 1
H H12 0.9720 0.1408 0.3185 0.049 Uiso calc R 1 1
C C13 0.8549(2) 0.1366(3) 0.3294(2) 0.0335(9) Uani d . 1 1
C C14 0.8288(2) 0.1492(3) 0.2480(2) 0.0372(10) Uani d . 1 1
Cl Cl1 0.66197(6) -0.07431(9) 0.32957(6) 0.0452(3) Uani d . 1 1
Cl Cl2 0.66507(6) 0.37138(8) 0.53645(6) 0.0394(3) Uani d . 1 1
Mn Mn1 0.66806(3) 0.12632(5) 0.33544(3) 0.0327(2) Uani d . 1 1
N N1 0.67083(16) 0.1169(2) 0.46588(16) 0.0272(7) Uani d . 1 1
N N2 0.79438(17) 0.1286(3) 0.37808(17) 0.0298(7) Uani d . 1 1
O O1 0.53707(15) 0.1347(2) 0.39159(15) 0.0420(7) Uani d . 1 1
O O2 0.46892(15) 0.1262(2) 0.50065(15) 0.0426(7) Uani d . 1 1
H H2 0.4322 0.1424 0.4732 0.064 Uiso calc R 1 1
O O3 0.83346(16) 0.0893(3) 0.68621(16) 0.0494(8) Uani d . 1 1
O O4 0.96201(16) 0.1034(2) 0.59366(16) 0.0508(8) Uani d . 1 1
O O5 0.75973(15) 0.1493(2) 0.23147(15) 0.0459(8) Uani d . 1 1
O O6 0.88584(15) 0.1576(3) 0.19872(14) 0.0465(8) Uani d . 1 1
H H6 0.8682 0.1559 0.1554 0.070 Uiso calc R 1 1
O O1W 0.59722(15) 0.1543(2) 0.23277(14) 0.0432(8) Uani d . 1 1
H H1W 0.5663 0.1036 0.2212 0.065 Uiso d R 1 1
H H2W 0.5724 0.2098 0.2383 0.065 Uiso d R 1 1
O O2W 0.66687(16) 0.3062(2) 0.35021(15) 0.0473(8) Uani d . 1 1
H H3W 0.6620 0.3250 0.3960 0.071 Uiso d R 1 1
H H4W 0.7070 0.3410 0.3480 0.071 Uiso d R 1 1
O O3W 0.34424(15) 0.1721(2) 0.42079(15) 0.0442(8) Uani d . 1 1
H H5W 0.2975 0.1564 0.4259 0.066 Uiso d R 1 1
H H6W 0.3519 0.1634 0.3756 0.066 Uiso d R 1 1
O O4W 0.5000 0.3286(4) 0.2500 0.0576(12) Uani d S 1 2
H H7W 0.5010 0.3685 0.2130 0.086 Uiso d R 1 1
O O5W 0.5000 -0.0309(4) 0.2500 0.0614(13) Uani d S 1 2
H H8W 0.5320 -0.0690 0.2720 0.092 Uiso d 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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 O2 125.5(3)
O1 C1 C2 121.2(3)
O2 C1 C2 113.2(3)
N1 C2 C3 123.2(3)
N1 C2 C1 112.0(3)
C3 C2 C1 124.8(3)
C2 C3 C4 118.4(4)
C2 C3 H3 120.8
C4 C3 H3 120.8
C5 C4 C3 119.3(4)
C5 C4 H4 120.3
C3 C4 H4 120.3
C4 C5 C6 118.4(3)
C4 C5 C7 121.4(3)
C6 C5 C7 120.2(3)
N1 C6 C5 122.7(3)
N1 C6 C10 114.9(3)
C5 C6 C10 122.4(3)
O3 C7 C5 122.9(4)
O3 C7 C8 119.9(4)
C5 C7 C8 117.2(3)
O4 C8 C9 122.3(4)
O4 C8 C7 118.8(4)
C9 C8 C7 118.9(3)
C11 C9 C10 117.6(3)
C11 C9 C8 122.5(3)
C10 C9 C8 119.9(3)
N2 C10 C9 122.5(3)
N2 C10 C6 116.0(3)
C9 C10 C6 121.5(3)
C12 C11 C9 119.7(4)
C12 C11 H11 120.1
C9 C11 H11 120.1
C13 C12 C11 118.6(4)
C13 C12 H12 120.7
C11 C12 H12 120.7
N2 C13 C12 122.6(4)
N2 C13 C14 112.3(3)
C12 C13 C14 125.1(3)
O5 C14 O6 124.6(4)
O5 C14 C13 121.1(3)
O6 C14 C13 114.3(3)
O1W Mn1 O2W 86.16(10)
O1W Mn1 N1 146.79(10)
O2W Mn1 N1 86.30(10)
O1W Mn1 N2 141.93(10)
O2W Mn1 N2 87.65(11)
N1 Mn1 N2 69.84(10)
O1W Mn1 O5 74.02(10)
O2W Mn1 O5 88.62(10)
N1 Mn1 O5 138.00(10)
N2 Mn1 O5 68.31(10)
O1W Mn1 O1 79.38(10)
O2W Mn1 O1 84.47(10)
N1 Mn1 O1 67.72(9)
N2 Mn1 O1 137.21(11)
O5 Mn1 O1 152.90(9)
O1W Mn1 Cl1 95.75(8)
O2W Mn1 Cl1 174.84(8)
N1 Mn1 Cl1 89.51(8)
N2 Mn1 Cl1 93.74(8)
O5 Mn1 Cl1 96.51(8)
O1 Mn1 Cl1 91.16(7)
C6 N1 C2 118.0(3)
C6 N1 Mn1 119.5(2)
C2 N1 Mn1 122.4(2)
C10 N2 C13 118.9(3)
C10 N2 Mn1 119.6(2)
C13 N2 Mn1 121.5(2)
C1 O1 Mn1 116.4(2)
C1 O2 H2 109.5
C14 O5 Mn1 116.8(2)
C14 O6 H6 109.5
Mn1 O1W H1W 115.2
Mn1 O1W H2W 108.9
H1W O1W H2W 109.1
Mn1 O2W H3W 112.7
Mn1 O2W H4W 120.9
H3W O2W H4W 89.1
H5W O3W H6W 103.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.217(4)
C1 O2 1.311(4)
C1 C2 1.508(5)
C2 N1 1.350(4)
C2 C3 1.382(5)
C3 C4 1.395(5)
C3 H3 0.9300
C4 C5 1.391(5)
C4 H4 0.9300
C5 C6 1.395(5)
C5 C7 1.510(5)
C6 N1 1.345(4)
C6 C10 1.482(5)
C7 O3 1.207(5)
C7 C8 1.559(6)
C8 O4 1.222(5)
C8 C9 1.485(5)
C9 C11 1.395(5)
C9 C10 1.414(5)
C10 N2 1.326(5)
C11 C12 1.386(5)
C11 H11 0.9300
C12 C13 1.384(5)
C12 H12 0.9300
C13 N2 1.351(5)
C13 C14 1.506(6)
C14 O5 1.222(4)
C14 O6 1.313(5)
Cl1 Mn1 2.4945(15)
Mn1 O1W 2.204(3)
Mn1 O2W 2.248(3)
Mn1 N1 2.295(3)
Mn1 N2 2.298(3)
Mn1 O5 2.430(3)
Mn1 O1 2.461(3)
O2 H2 0.8200
O6 H6 0.8200
O1W H1W 0.8476
O1W H2W 0.8169
O2W H3W 0.8416
O2W H4W 0.8142
O3W H5W 0.8312
O3W H6W 0.8126
O4W H7W 0.8173
O5W H8W 0.8221
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
C11 H11 Cl2 4_556 0.93 2.89 3.799(3) 165.9
C12 H12 O6 3_755 0.93 2.47 3.283(5) 145.8
C4 H4 Cl1 7_556 0.93 2.72 3.640(4) 170.8
O5W H8W Cl1 . 0.82 2.45 3.1625(16) 145.0
O4W H7W O4 2_654 0.82 2.22 2.947(3) 148.5
O3W H6W O5 3_655 0.81 2.69 3.230(4) 125.1
O3W H6W O1W 3_655 0.81 2.10 2.888(4) 164.2
O3W H5W Cl2 4_456 0.83 2.40 3.217(3) 169.0
O2W H4W Cl1 8_765 0.82 2.51 3.315(3) 171.5
O2W H3W Cl2 . 0.84 2.53 3.371(3) 172.4
O1W H2W O4W . 0.82 1.94 2.751(4) 171.7
O1W H1W O5W . 0.85 2.08 2.858(5) 151.4
O6 H6 Cl2 2_654 0.82 2.19 3.004(3) 170.1
O2 H2 O3W . 0.82 1.81 2.625(4) 173.6
