#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/27/4502779.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_4502779
loop_
_publ_author_name
'Xin, Ling-Yun'
'Liu, Guang-Zhen'
'Li, Xiao-Ling'
'Wang, Li-Ya'
_publ_section_title
;
 Structural Diversity for a Series of Metal(II) Complexes Based on
 Flexible 1,2-Phenylenediacetate and Dipyridyl-type Coligand
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              147
_journal_paper_doi               10.1021/cg200903k
_journal_volume                  12
_journal_year                    2012
_chemical_formula_sum            'C11 H11 Mn0.5 N O2.5'
_chemical_formula_weight         224.68
_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                 104.481(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.3501(19)
_cell_length_b                   18.330(3)
_cell_length_c                   8.5877(12)
_cell_measurement_reflns_used    1930
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.58
_cell_measurement_theta_min      2.79
_cell_volume                     2034.7(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9384
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         2.79
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_T_max  0.9161
_exptl_absorpt_correction_T_min  0.8418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             932
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.050
_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     137
_refine_ls_number_reflns         2524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0380
_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)+(0.0294P)²+1.6301P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0862
_reflns_number_gt                1853
_reflns_number_total             2524
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200903k_si_013.cif
_cod_data_source_block           a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C11 H11 Mn0.50 N O2.50'
_cod_database_code               4502779
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
Mn1 Mn 0.5000 0.61416(2) 0.7500 0.03371(13) Uani 1 2 d S
N1 N 0.33816(12) 0.61074(9) 0.57716(19) 0.0389(4) Uani 1 1 d .
O1 O 0.43836(12) 0.59622(8) 0.99255(18) 0.0517(4) Uani 1 1 d .
O2 O 0.45074(12) 0.70438(8) 0.89470(17) 0.0499(4) Uani 1 1 d .
O3W O 0.5000 0.49469(11) 0.7500 0.0482(5) Uani 1 2 d S
H1W H 0.4923 0.4750 0.8359 0.072 Uiso 1 1 d R
C1 C 0.43102(14) 0.66416(11) 1.0002(2) 0.0372(5) Uani 1 1 d .
C2 C 0.39593(16) 0.69847(12) 1.1388(2) 0.0436(5) Uani 1 1 d .
H2A H 0.3221 0.7075 1.1046 0.052 Uiso 1 1 calc R
H2B H 0.4078 0.6640 1.2273 0.052 Uiso 1 1 calc R
C3 C 0.45033(15) 0.76904(11) 1.1982(2) 0.0393(5) Uani 1 1 d .
C4 C 0.40309(19) 0.83561(13) 1.1498(3) 0.0545(6) Uani 1 1 d .
H4 H 0.3369 0.8361 1.0816 0.065 Uiso 1 1 calc R
C5 C 0.4514(2) 0.90066(13) 1.2000(3) 0.0655(7) Uani 1 1 d .
H5 H 0.4181 0.9445 1.1659 0.079 Uiso 1 1 calc R
C6 C 0.26393(16) 0.65793(12) 0.5847(3) 0.0485(6) Uani 1 1 d .
H6 H 0.2765 0.6909 0.6697 0.058 Uiso 1 1 calc R
C7 C 0.16908(16) 0.66083(13) 0.4736(3) 0.0520(6) Uani 1 1 d .
H7 H 0.1196 0.6946 0.4856 0.062 Uiso 1 1 calc R
C8 C 0.14807(14) 0.61331(11) 0.3443(2) 0.0381(4) Uani 1 1 d .
C9 C 0.22503(15) 0.56449(12) 0.3362(3) 0.0441(5) Uani 1 1 d .
H9 H 0.2148 0.5313 0.2517 0.053 Uiso 1 1 calc R
C10 C 0.31743(16) 0.56458(12) 0.4531(3) 0.0454(5) Uani 1 1 d .
H10 H 0.3677 0.5307 0.4449 0.054 Uiso 1 1 calc R
C11 C 0.04705(14) 0.61543(13) 0.2164(3) 0.0455(5) Uani 1 1 d .
H11A H 0.0458 0.6589 0.1514 0.055 Uiso 1 1 calc R
H11B H 0.0437 0.5734 0.1465 0.055 Uiso 1 1 calc R
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O3W Mn1 O2 136.96(4) . .
O3W Mn1 O2 136.96(4) . 2_656
O2 Mn1 O2 86.09(8) . 2_656
O3W Mn1 N1 88.44(4) . 2_656
O2 Mn1 N1 91.18(6) . 2_656
O2 Mn1 N1 91.10(6) 2_656 2_656
O3W Mn1 N1 88.44(4) . .
O2 Mn1 N1 91.10(6) . .
O2 Mn1 N1 91.18(6) 2_656 .
N1 Mn1 N1 176.87(9) 2_656 .
O3W Mn1 O1 82.27(3) . .
O2 Mn1 O1 54.88(5) . .
O2 Mn1 O1 140.53(5) 2_656 .
N1 Mn1 O1 84.74(6) 2_656 .
N1 Mn1 O1 94.84(6) . .
O3W Mn1 O1 82.27(3) . 2_656
O2 Mn1 O1 140.53(5) . 2_656
O2 Mn1 O1 54.88(5) 2_656 2_656
N1 Mn1 O1 94.84(6) 2_656 2_656
N1 Mn1 O1 84.74(6) . 2_656
O1 Mn1 O1 164.54(7) . 2_656
C6 N1 C10 116.32(16) . .
C6 N1 Mn1 122.90(13) . .
C10 N1 Mn1 120.49(13) . .
C1 O1 Mn1 87.63(13) . .
C1 O2 Mn1 96.34(13) . .
Mn1 O3W H1W 115.1 . .
O2 C1 O1 121.1(2) . .
O2 C1 C2 119.15(18) . .
O1 C1 C2 119.76(19) . .
C3 C2 C1 113.75(17) . .
C3 C2 H2A 108.8 . .
C1 C2 H2A 108.8 . .
C3 C2 H2B 108.8 . .
C1 C2 H2B 108.8 . .
H2A C2 H2B 107.7 . .
C4 C3 C3 118.51(13) . 2_657
C4 C3 C2 120.54(19) . .
C3 C3 C2 120.95(11) 2_657 .
C5 C4 C3 121.8(2) . .
C5 C4 H4 119.1 . .
C3 C4 H4 119.1 . .
C5 C5 C4 119.70(14) 2_657 .
C5 C5 H5 120.2 2_657 .
C4 C5 H5 120.2 . .
N1 C6 C7 123.8(2) . .
N1 C6 H6 118.1 . .
C7 C6 H6 118.1 . .
C6 C7 C8 119.8(2) . .
C6 C7 H7 120.1 . .
C8 C7 H7 120.1 . .
C9 C8 C7 116.47(18) . .
C9 C8 C11 121.40(18) . .
C7 C8 C11 122.12(19) . .
C8 C9 C10 120.26(19) . .
C8 C9 H9 119.9 . .
C10 C9 H9 119.9 . .
N1 C10 C9 123.37(19) . .
N1 C10 H10 118.3 . .
C9 C10 H10 118.3 . .
C11 C11 C8 113.5(2) 2 .
C11 C11 H11A 108.9 2 .
C8 C11 H11A 108.9 . .
C11 C11 H11B 108.9 2 .
C8 C11 H11B 108.9 . .
H11A C11 H11B 107.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mn1 O3W 2.190(2) .
Mn1 O2 2.2626(15) .
Mn1 O2 2.2626(15) 2_656
Mn1 N1 2.2959(15) 2_656
Mn1 N1 2.2959(15) .
Mn1 O1 2.4456(16) .
Mn1 O1 2.4456(16) 2_656
N1 C6 1.329(3) .
N1 C10 1.334(3) .
O1 C1 1.252(2) .
O2 C1 1.246(2) .
O3W H1W 0.8500 .
C1 C2 1.520(3) .
C2 C3 1.508(3) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.389(3) .
C3 C3 1.400(4) 2_657
C4 C5 1.373(3) .
C4 H4 0.9300 .
C5 C5 1.365(5) 2_657
C5 H5 0.9300 .
C6 C7 1.383(3) .
C6 H6 0.9300 .
C7 C8 1.383(3) .
C7 H7 0.9300 .
C8 C9 1.377(3) .
C8 C11 1.512(3) .
C9 C10 1.382(3) .
C9 H9 0.9300 .
C10 H10 0.9300 .
C11 C11 1.508(4) 2
C11 H11A 0.9700 .
C11 H11B 0.9700 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3W H1W O1 0.85 2.01 2.7262(19) 141.0 5_667
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
_geom_torsion_site_symmetry_4
O3W Mn1 N1 C6 142.47(17) . .
O2 Mn1 N1 C6 5.52(17) . .
O2 Mn1 N1 C6 -80.59(17) 2_656 .
N1 Mn1 N1 C6 142.47(17) 2_656 .
O1 Mn1 N1 C6 60.36(17) . .
O1 Mn1 N1 C6 -135.15(17) 2_656 .
O3W Mn1 N1 C10 -43.94(16) . .
O2 Mn1 N1 C10 179.12(16) . .
O2 Mn1 N1 C10 93.01(17) 2_656 .
N1 Mn1 N1 C10 -43.94(16) 2_656 .
O1 Mn1 N1 C10 -126.04(16) . .
O1 Mn1 N1 C10 38.44(16) 2_656 .
O3W Mn1 O1 C1 -177.26(11) . .
O2 Mn1 O1 C1 -1.56(11) . .
O2 Mn1 O1 C1 8.27(15) 2_656 .
N1 Mn1 O1 C1 93.61(12) 2_656 .
N1 Mn1 O1 C1 -89.50(12) . .
O1 Mn1 O1 C1 -177.26(11) 2_656 .
O3W Mn1 O2 C1 7.82(14) . .
O2 Mn1 O2 C1 -172.18(14) 2_656 .
N1 Mn1 O2 C1 -81.15(12) 2_656 .
N1 Mn1 O2 C1 96.71(12) . .
O1 Mn1 O2 C1 1.57(11) . .
O1 Mn1 O2 C1 179.77(11) 2_656 .
Mn1 O2 C1 O1 -2.9(2) . .
Mn1 O2 C1 C2 178.02(14) . .
Mn1 O1 C1 O2 2.70(18) . .
Mn1 O1 C1 C2 -178.26(15) . .
O2 C1 C2 C3 -38.1(3) . .
O1 C1 C2 C3 142.84(19) . .
C1 C2 C3 C4 99.5(2) . .
C1 C2 C3 C3 -79.9(3) . 2_657
C3 C3 C4 C5 0.5(4) 2_657 .
C2 C3 C4 C5 -179.0(2) . .
C3 C4 C5 C5 0.0(5) . 2_657
C10 N1 C6 C7 0.3(3) . .
Mn1 N1 C6 C7 174.18(18) . .
N1 C6 C7 C8 -0.9(4) . .
C6 C7 C8 C9 0.7(3) . .
C6 C7 C8 C11 -178.1(2) . .
C7 C8 C9 C10 0.0(3) . .
C11 C8 C9 C10 178.8(2) . .
C6 N1 C10 C9 0.4(3) . .
Mn1 N1 C10 C9 -173.65(17) . .
C8 C9 C10 N1 -0.5(4) . .
C9 C8 C11 C11 131.15(17) . 2
C7 C8 C11 C11 -50.1(2) . 2
