#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/11/2221107.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_2221107
loop_
_publ_author_name
'Sertçelik, Mustafa'
'Tercan, Barış'
'Şahin, Ertan'
'Necefoğlu, Hacali'
'Hökelek, Tuncer'
_publ_section_title
Diaquabis(N,N-diethylnicotinamide-κN¹)bis(4-formylbenzoato-κO¹)manganese(II)
_journal_coeditor_code           HY2182
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m324
_journal_page_last               m325
_journal_paper_doi               10.1107/S1600536809006047
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Mn (C8 H5 O3)2 (C10 H14 N2 O)2 (H2 O)2]'
_chemical_formula_moiety         'C36 H42 Mn N4 O10'
_chemical_formula_sum            'C36 H42 Mn N4 O10'
_chemical_formula_weight         745.68
_chemical_name_systematic
;
Diaquabis(N,N-diethylnicotinamide-κN¹)bis(4-
formylbenzoato-κO¹)manganese(II)
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                86.381(8)
_cell_angle_beta                 78.272(7)
_cell_angle_gamma                68.618(6)
_cell_formula_units_Z            1
_cell_length_a                   7.3266(2)
_cell_length_b                   8.6618(2)
_cell_length_c                   16.0687(3)
_cell_measurement_reflns_used    2942
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      26.40
_cell_measurement_theta_min      2.53
_cell_volume                     929.67(6)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID-S'
_diffrn_measurement_method       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  0.0707
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18356
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    0.416
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             391
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.769
_refine_diff_density_min         -0.320
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3799
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0576
_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)+(0.0681P)²+0.7177P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1508
_refine_ls_wR_factor_ref         0.1572
_reflns_number_gt                3317
_reflns_number_total             3799
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hy2182.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_database_code               2221107
_cod_database_fobs_code          2221107
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_disorder_assembly
_atom_site_disorder_group
Mn Mn1 0.5000 0.5000 0.5000 0.04035(19) Uani d S 1 . .
O O1 0.5226(3) 0.6203(2) 0.60914(12) 0.0488(5) Uani d . 1 . .
O O2 0.2455(3) 0.6315(3) 0.70146(14) 0.0583(5) Uani d . 1 . .
O O3 0.9452(5) 0.6893(5) 0.95632(19) 0.1013(11) Uani d . 1 . .
O O4 -0.2292(3) 0.8295(3) 0.37375(14) 0.0615(6) Uani d . 1 . .
O O5 0.2143(3) 0.4822(3) 0.56750(14) 0.0548(5) Uani d D 1 . .
H H51 0.209(7) 0.378(3) 0.579(3) 0.089(13) Uiso d D 1 . .
H H52 0.202(7) 0.529(5) 0.6197(17) 0.095(14) Uiso d D 1 . .
N N1 0.3151(3) 0.7460(3) 0.44777(14) 0.0440(5) Uani d . 1 . .
N N2 -0.1135(5) 0.9208(4) 0.24863(17) 0.0644(7) Uani d . 1 . .
C C1 0.4205(4) 0.6295(3) 0.68336(17) 0.0439(6) Uani d . 1 . .
C C2 0.5205(4) 0.6365(3) 0.75573(17) 0.0428(6) Uani d . 1 . .
C C3 0.7119(4) 0.6417(4) 0.74021(17) 0.0473(6) Uani d . 1 . .
H H3 0.7806 0.6384 0.6845 0.057 Uiso calc R 1 . .
C C4 0.8014(5) 0.6518(4) 0.80646(19) 0.0532(7) Uani d . 1 . .
H H4 0.9292 0.6560 0.7954 0.064 Uiso calc R 1 . .
C C5 0.6993(5) 0.6556(4) 0.88983(19) 0.0551(7) Uani d . 1 . .
C C6 0.5098(5) 0.6475(4) 0.90521(19) 0.0579(8) Uani d . 1 . .
H H6 0.4424 0.6482 0.9609 0.069 Uiso calc R 1 . .
C C7 0.4202(4) 0.6384(4) 0.83915(18) 0.0519(7) Uani d . 1 . .
H H7 0.2927 0.6336 0.8503 0.062 Uiso calc R 1 . .
C C8 0.7904(7) 0.6678(6) 0.9615(2) 0.0760(11) Uani d D 1 . .
H H8 0.712(5) 0.658(4) 1.0166(14) 0.062(10) Uiso d D 1 . .
C C9 0.3345(4) 0.8906(3) 0.45861(18) 0.0470(6) Uani d . 1 . .
H H9 0.4275 0.8922 0.4899 0.056 Uiso calc R 1 . .
C C10 0.2234(5) 1.0371(4) 0.4256(2) 0.0525(7) Uani d . 1 . .
H H10 0.2408 1.1354 0.4348 0.063 Uiso calc R 1 . .
C C11 0.0859(4) 1.0359(3) 0.37870(19) 0.0498(7) Uani d . 1 . .
H H11 0.0102 1.1330 0.3550 0.060 Uiso calc R 1 . .
C C12 0.0623(4) 0.8875(3) 0.36748(17) 0.0430(6) Uani d . 1 . .
C C13 0.1776(4) 0.7474(3) 0.40382(17) 0.0446(6) Uani d . 1 . .
H H13 0.1590 0.6484 0.3976 0.054 Uiso calc R 1 . .
C C14 -0.1018(4) 0.8756(4) 0.32858(19) 0.0495(7) Uani d . 1 . .
C C15 0.0357(6) 0.9707(5) 0.1895(2) 0.0743(10) Uani d . 1 . .
H H15A -0.0323 1.0752 0.1641 0.089 Uiso calc R 1 . .
H H15B 0.1251 0.9892 0.2214 0.089 Uiso calc R 1 . .
C C16 0.1546(9) 0.8495(9) 0.1215(4) 0.141(3) Uani d . 1 . .
H H16A 0.2588 0.8837 0.0896 0.212 Uiso calc R 1 . .
H H16B 0.0702 0.8423 0.0845 0.212 Uiso calc R 1 . .
H H16C 0.2126 0.7429 0.1459 0.212 Uiso calc R 1 . .
C C17 -0.2907(7) 0.9202(5) 0.2173(3) 0.0779(11) Uani d . 1 . .
H H17A -0.4094 0.9678 0.2607 0.093 Uiso calc R 1 . .
H H17B -0.3065 0.9890 0.1673 0.093 Uiso calc R 1 . .
C C18 -0.2717(9) 0.7511(6) 0.1959(3) 0.1023(16) Uani d . 1 . .
H H18A -0.3799 0.7568 0.1692 0.153 Uiso calc R 1 . .
H H18B -0.2757 0.6873 0.2468 0.153 Uiso calc R 1 . .
H H18C -0.1470 0.6992 0.1576 0.153 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Mn1 O1 2_666 . 180.0000(10) ?
O1 Mn1 O5 2_666 . 89.23(8) ?
O1 Mn1 O5 . . 90.77(8) ?
O1 Mn1 O5 2_666 2_666 90.77(8) ?
O1 Mn1 O5 . 2_666 89.23(8) ?
O1 Mn1 N1 2_666 2_666 92.23(8) ?
O1 Mn1 N1 . . 92.23(8) ?
O1 Mn1 N1 . 2_666 87.77(8) ?
O1 Mn1 N1 2_666 . 87.77(8) ?
O5 Mn1 O5 . 2_666 180.0000(10) ?
O5 Mn1 N1 . 2_666 92.95(8) ?
O5 Mn1 N1 2_666 2_666 87.05(8) ?
O5 Mn1 N1 . . 87.05(8) ?
O5 Mn1 N1 2_666 . 92.95(8) ?
N1 Mn1 N1 2_666 . 180.00(10) ?
Mn1 O5 H52 . . 101(3) ?
Mn1 O5 H51 . . 118(3) ?
H52 O5 H51 . . 106(4) ?
C1 O1 Mn1 . . 126.76(18) ?
C9 N1 C13 . . 117.3(2) ?
C9 N1 Mn1 . . 124.02(18) ?
C13 N1 Mn1 . . 118.65(17) ?
C14 N2 C15 . . 124.7(3) ?
C14 N2 C17 . . 117.3(3) ?
C15 N2 C17 . . 118.0(3) ?
O1 C1 C2 . . 116.8(2) ?
O2 C1 C2 . . 117.8(2) ?
O2 C1 O1 . . 125.4(3) ?
C3 C2 C1 . . 120.9(2) ?
C7 C2 C1 . . 119.8(3) ?
C7 C2 C3 . . 119.3(3) ?
C2 C3 H3 . . 119.6 ?
C4 C3 C2 . . 120.9(3) ?
C4 C3 H3 . . 119.6 ?
C3 C4 C5 . . 119.6(3) ?
C3 C4 H4 . . 120.2 ?
C5 C4 H4 . . 120.2 ?
C4 C5 C8 . . 120.7(3) ?
C6 C5 C4 . . 119.5(3) ?
C6 C5 C8 . . 119.9(3) ?
C5 C6 H6 . . 119.5 ?
C7 C6 C5 . . 120.9(3) ?
C7 C6 H6 . . 119.5 ?
C2 C7 H7 . . 120.1 ?
C6 C7 C2 . . 119.9(3) ?
C6 C7 H7 . . 120.1 ?
O3 C8 C5 . . 126.0(4) ?
O3 C8 H8 . . 121(2) ?
C5 C8 H8 . . 113(2) ?
N1 C9 C10 . . 123.1(3) ?
N1 C9 H9 . . 118.4 ?
C10 C9 H9 . . 118.4 ?
C9 C10 C11 . . 118.9(3) ?
C9 C10 H10 . . 120.6 ?
C11 C10 H10 . . 120.6 ?
C10 C11 C12 . . 118.8(3) ?
C10 C11 H11 . . 120.6 ?
C12 C11 H11 . . 120.6 ?
C11 C12 C14 . . 123.3(2) ?
C13 C12 C11 . . 118.3(3) ?
C13 C12 C14 . . 117.8(2) ?
N1 C13 C12 . . 123.5(3) ?
N1 C13 H13 . . 118.3 ?
C12 C13 H13 . . 118.3 ?
O4 C14 N2 . . 121.2(3) ?
O4 C14 C12 . . 118.1(3) ?
N2 C14 C12 . . 120.6(3) ?
N2 C15 H15A . . 108.7 ?
N2 C15 H15B . . 108.7 ?
C16 C15 N2 . . 114.1(4) ?
C16 C15 H15A . . 108.7 ?
C16 C15 H15B . . 108.7 ?
H15A C15 H15B . . 107.6 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16B . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
N2 C17 H17A . . 109.2 ?
N2 C17 H17B . . 109.2 ?
C18 C17 N2 . . 111.8(4) ?
C18 C17 H17A . . 109.2 ?
C18 C17 H17B . . 109.2 ?
H17A C17 H17B . . 107.9 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18B . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Mn1 O1 2_666 2.1596(18) ?
Mn1 O1 . 2.1596(18) yes
Mn1 O5 . 2.207(2) yes
Mn1 O5 2_666 2.207(2) ?
Mn1 N1 . 2.283(2) yes
Mn1 N1 2_666 2.283(2) ?
O1 C1 . 1.262(3) ?
O2 C1 . 1.249(3) ?
O3 C8 . 1.201(5) ?
O4 C14 . 1.232(4) ?
O5 H51 . 0.924(19) ?
O5 H52 . 0.926(19) ?
N1 C9 . 1.337(3) ?
N1 C13 . 1.339(3) ?
N2 C14 . 1.330(4) ?
N2 C15 . 1.468(5) ?
N2 C17 . 1.487(4) ?
C2 C1 . 1.510(4) ?
C2 C3 . 1.391(4) ?
C2 C7 . 1.389(4) ?
C3 C4 . 1.381(4) ?
C3 H3 . 0.9300 ?
C4 H4 . 0.9300 ?
C5 C4 . 1.391(4) ?
C5 C6 . 1.386(5) ?
C5 C8 . 1.470(4) ?
C6 H6 . 0.9300 ?
C7 C6 . 1.377(4) ?
C7 H7 . 0.9300 ?
C8 H8 . 0.971(18) ?
C9 C10 . 1.375(4) ?
C9 H9 . 0.9300 ?
C10 H10 . 0.9300 ?
C11 C10 . 1.379(4) ?
C11 H11 . 0.9300 ?
C12 C11 . 1.385(4) ?
C12 C13 . 1.375(4) ?
C12 C14 . 1.500(4) ?
C13 H13 . 0.9300 ?
C15 C16 . 1.465(7) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 C18 . 1.477(6) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 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
O5 H51 O4 2_566 0.92(3) 1.87(3) 2.775(3) 165(4) yes
O5 H52 O2 . 0.93(3) 1.77(4) 2.669(3) 162(4) 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_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O5 Mn1 O1 C1 . . . . 13.3(2) ?
O5 Mn1 O1 C1 2_666 . . . -166.7(2) ?
N1 Mn1 O1 C1 2_666 . . . -79.6(2) ?
N1 Mn1 O1 C1 . . . . 100.4(2) ?
O1 Mn1 N1 C9 2_666 . . . -148.3(2) ?
O1 Mn1 N1 C9 . . . . 31.7(2) ?
O1 Mn1 N1 C13 2_666 . . . 32.1(2) ?
O1 Mn1 N1 C13 . . . . -147.9(2) ?
O5 Mn1 N1 C9 . . . . 122.4(2) ?
O5 Mn1 N1 C9 2_666 . . . -57.6(2) ?
O5 Mn1 N1 C13 . . . . -57.2(2) ?
O5 Mn1 N1 C13 2_666 . . . 122.8(2) ?
Mn1 O1 C1 O2 . . . . -29.8(4) ?
Mn1 O1 C1 C2 . . . . 149.49(18) ?
Mn1 N1 C9 C10 . . . . 179.1(2) ?
C13 N1 C9 C10 . . . . -1.2(4) ?
Mn1 N1 C13 C12 . . . . -178.0(2) ?
C9 N1 C13 C12 . . . . 2.3(4) ?
C15 N2 C14 O4 . . . . -177.4(3) ?
C17 N2 C14 O4 . . . . 2.5(5) ?
C15 N2 C14 C12 . . . . 5.6(5) ?
C17 N2 C14 C12 . . . . -174.4(3) ?
C14 N2 C15 C16 . . . . 108.8(5) ?
C17 N2 C15 C16 . . . . -71.1(5) ?
C14 N2 C17 C18 . . . . -78.2(5) ?
C15 N2 C17 C18 . . . . 101.7(4) ?
C3 C2 C1 O1 . . . . 3.4(4) ?
C7 C2 C1 O1 . . . . -176.9(2) ?
C3 C2 C1 O2 . . . . -177.3(3) ?
C7 C2 C1 O2 . . . . 2.5(4) ?
C1 C2 C3 C4 . . . . 178.6(3) ?
C7 C2 C3 C4 . . . . -1.2(4) ?
C1 C2 C7 C6 . . . . -178.9(3) ?
C3 C2 C7 C6 . . . . 0.8(4) ?
C2 C3 C4 C5 . . . . 0.4(5) ?
C6 C5 C4 C3 . . . . 0.7(5) ?
C8 C5 C4 C3 . . . . -179.5(3) ?
C4 C5 C6 C7 . . . . -1.1(5) ?
C8 C5 C6 C7 . . . . 179.1(4) ?
C4 C5 C8 O3 . . . . 6.7(7) ?
C6 C5 C8 O3 . . . . -173.4(4) ?
C2 C7 C6 C5 . . . . 0.3(5) ?
N1 C9 C10 C11 . . . . -0.3(5) ?
C12 C11 C10 C9 . . . . 0.9(5) ?
C13 C12 C11 C10 . . . . 0.0(4) ?
C14 C12 C11 C10 . . . . 171.0(3) ?
C11 C12 C13 N1 . . . . -1.7(4) ?
C14 C12 C13 N1 . . . . -173.2(3) ?
C11 C12 C14 O4 . . . . -114.4(3) ?
C11 C12 C14 N2 . . . . 62.7(4) ?
C13 C12 C14 O4 . . . . 56.7(4) ?
C13 C12 C14 N2 . . . . -126.3(3) ?
