#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:53:39 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179602 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/66/4506692.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_4506692
loop_
_publ_author_name
'Déniz, Mariadel'
'Hernández-Rodríguez, Irene'
'Pasán, Jorge'
'Fabelo, Oscar'
'Cañadillas-Delgado, Laura'
'Yuste, Consuelo'
'Julve, Miguel'
'Lloret, Francesc'
'Ruiz-Pérez, Catalina'
_publ_section_title
;
 Pillaring Role of 4,4′-Azobis(pyridine) in Substituted
 Malonate-Containing Manganese(II) Complexes: Syntheses, Crystal
 Structures, and Magnetic Properties
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4505
_journal_paper_doi               10.1021/cg300670a
_journal_volume                  12
_journal_year                    2012
_chemical_formula_sum            'C19 H16 Mn N4 O5'
_chemical_formula_weight         435.30
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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            4
_cell_length_a                   37.055(2)
_cell_length_b                   7.3447(6)
_cell_length_c                   7.3447(5)
_cell_measurement_temperature    293(2)
_cell_volume                     1998.9(2)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92, J. Appl. Cryst. 26, 343-350, (1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_max       47
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            17313
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.54
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.698
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             892
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.196
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2464
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.1068
_refine_ls_R_factor_gt           0.0797
_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)+(0.0900P)²+8.5284P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2268
_refine_ls_wR_factor_ref         0.2418
_reflns_number_gt                1824
_reflns_number_total             2464
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg300670a_si_004.cif
_cod_data_source_block           new
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               4506692
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
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 0.77167(3) 0.2500 0.59923(14) 0.0308(4) Uani 1 2 d S
O1W O 0.72716(14) 0.2500 0.8077(7) 0.0396(12) Uani 1 2 d SD
O1 O 0.70116(10) -0.0286(5) 0.2338(5) 0.0409(9) Uani 1 1 d .
O2 O 0.74196(10) 0.0576(5) 0.4364(5) 0.0426(9) Uani 1 1 d .
N1 N 0.81841(18) 0.2500 0.3985(9) 0.0453(15) Uani 1 2 d S
C2 C 0.69047(18) 0.2500 0.3948(9) 0.0336(15) Uani 1 2 d S
H2 H 0.6877 0.2500 0.5275 0.040 Uiso 1 2 calc SR
C1 C 0.71283(13) 0.0799(7) 0.3490(6) 0.0324(10) Uani 1 1 d .
C7 C 0.5886(3) 0.2500 0.367(2) 0.104(5) Uani 1 2 d S
H7 H 0.5692 0.2500 0.4468 0.124 Uiso 1 2 calc SR
C11 C 0.8756(3) 0.2500 0.1542(14) 0.071(3) Uani 1 2 d SD
C8 C 0.6237(2) 0.2500 0.4355(17) 0.072(3) Uani 1 2 d S
H8 H 0.6275 0.2500 0.5606 0.087 Uiso 1 2 calc SR
C3 C 0.6526(2) 0.2500 0.3174(12) 0.0427(18) Uani 1 2 d S
C4 C 0.6458(3) 0.2500 0.1306(14) 0.067(3) Uani 1 2 d S
H4 H 0.6649 0.2500 0.0486 0.080 Uiso 1 2 calc SR
C10 C 0.8412(3) 0.2500 0.0967(13) 0.075(3) Uani 1 2 d S
H10 H 0.8360 0.2500 -0.0272 0.090 Uiso 1 2 calc SR
N2 N 0.9017(3) 0.2500 0.0038(15) 0.086(3) Uani 1 2 d SD
C9 C 0.8140(3) 0.2500 0.2212(12) 0.069(3) Uani 1 2 d S
H9 H 0.7904 0.2500 0.1773 0.083 Uiso 1 2 calc SR
C6 C 0.5824(3) 0.2500 0.190(3) 0.110(5) Uani 1 2 d S
H6 H 0.5588 0.2500 0.1477 0.132 Uiso 1 2 calc SR
C5 C 0.6105(3) 0.2500 0.067(2) 0.094(4) Uani 1 2 d S
H5 H 0.6059 0.2500 -0.0575 0.112 Uiso 1 2 calc SR
C13 C 0.8517(3) 0.2500 0.4552(15) 0.103(6) Uani 1 2 d S
H13 H 0.8561 0.2500 0.5799 0.124 Uiso 1 2 calc SR
C12 C 0.8808(3) 0.2500 0.3376(18) 0.137(8) Uani 1 2 d S
H12 H 0.9042 0.2500 0.3841 0.165 Uiso 1 2 calc SR
N3 N 0.9304(3) 0.2500 0.0605(16) 0.123(5) Uani 1 2 d SD
C14 C 0.9784(3) 0.2500 -0.3961(14) 0.148(8) Uani 1 2 d SGD
H14 H 0.9751 0.2872 -0.5160 0.178 Uiso 0.50 1 calc PR
C15 C 0.9514(3) 0.2791(11) -0.2681(18) 0.128(9) Uani 0.50 1 d PGD
H15 H 0.9300 0.3357 -0.3023 0.154 Uiso 0.50 1 calc PR
C16 C 0.9563(3) 0.2234(17) -0.0889(16) 0.116(8) Uani 0.50 1 d PGD
C18 C 0.9883(3) 0.139(2) -0.0378(13) 0.165(12) Uani 0.50 1 d PGD
H18 H 0.9916 0.1015 0.0821 0.198 Uiso 0.50 1 calc PR
C17 C 1.0153(3) 0.110(2) -0.1658(17) 0.115(8) Uani 0.50 1 d PGD
H17 H 1.0367 0.0530 -0.1316 0.138 Uiso 0.50 1 calc PR
N4 N 1.0104(3) 0.1653(14) -0.3449(16) 0.121(8) Uani 0.50 1 d PGD
H1WA H 0.7365(16) 0.1547(14) 0.867(7) 0.09(3) Uiso 1 1 d D
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
O1 Mn1 O1 98.1(2) 7_766 2_655
O1 Mn1 O2 171.68(14) 7_766 .
O1 Mn1 O2 89.92(14) 2_655 .
O1 Mn1 O2 89.92(14) 7_766 8_565
O1 Mn1 O2 171.68(14) 2_655 8_565
O2 Mn1 O2 81.98(19) . 8_565
O1 Mn1 O1W 91.75(13) 7_766 .
O1 Mn1 O1W 91.75(13) 2_655 .
O2 Mn1 O1W 90.18(15) . .
O2 Mn1 O1W 90.18(15) 8_565 .
O1 Mn1 N1 86.64(14) 7_766 .
O1 Mn1 N1 86.64(14) 2_655 .
O2 Mn1 N1 91.68(16) . .
O2 Mn1 N1 91.68(16) 8_565 .
O1W Mn1 N1 177.5(2) . .
C1 O1 Mn1 129.5(3) . 2_654
C1 O2 Mn1 129.2(3) . .
C13 N1 C9 115.8(8) . .
C13 N1 Mn1 121.0(6) . .
C9 N1 Mn1 123.2(6) . .
C3 C2 C1 114.7(4) . 8_565
C3 C2 C1 114.7(4) . .
C1 C2 C1 108.8(5) 8_565 .
O1 C1 O2 124.0(4) . .
O1 C1 C2 118.9(5) . .
O2 C1 C2 117.0(5) . .
C6 C7 C8 121.2(13) . .
C10 C11 C12 116.5(9) . .
C10 C11 N2 112.8(10) . .
C12 C11 N2 130.7(12) . .
C3 C8 C7 119.8(12) . .
C8 C3 C4 118.5(9) . .
C8 C3 C2 119.0(8) . .
C4 C3 C2 122.5(8) . .
C5 C4 C3 120.2(11) . .
C11 C10 C9 119.5(9) . .
N3 N2 C11 109.8(12) . .
N1 C9 C10 125.0(10) . .
C7 C6 C5 121.0(12) . .
C6 C5 C4 119.3(13) . .
N1 C13 C12 122.7(10) . .
C11 C12 C13 120.5(11) . .
N2 N3 C16 109.7(11) . .
C15 C14 N4 120.0 . .
C16 C15 C14 120.0 . .
C18 C16 C15 120.0 . .
C18 C16 N3 114.5(10) . .
C15 C16 N3 125.5(10) . .
C18 C16 C18 65.7(9) . 8_565
C15 C16 C18 97.7(4) . 8_565
N3 C16 C18 103.0(8) . 8_565
C17 C18 C16 120.0 . .
C18 C17 N4 120.0 . .
C17 N4 C14 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mn1 O1 2.153(3) 7_766
Mn1 O1 2.153(3) 2_655
Mn1 O2 2.154(3) .
Mn1 O2 2.154(3) 8_565
Mn1 O1W 2.250(5) .
Mn1 N1 2.274(6) .
O1 C1 1.240(6) .
O1 Mn1 2.153(3) 2_654
O2 C1 1.266(6) .
N1 C13 1.303(12) .
N1 C9 1.313(10) .
C2 C3 1.514(10) .
C2 C1 1.536(6) 8_565
C2 C1 1.536(6) .
C7 C6 1.32(2) .
C7 C8 1.396(16) .
C11 C10 1.343(15) .
C11 C12 1.361(16) .
C11 N2 1.468(12) .
C8 C3 1.379(12) .
C3 C4 1.395(13) .
C4 C5 1.387(14) .
C10 C9 1.362(13) .
N2 N3 1.141(11) .
C6 C5 1.38(2) .
C13 C12 1.382(15) .
N3 C16 1.473(12) .
C14 C15 1.3900 .
C14 N4 1.3900 .
C15 C16 1.3900 .
C16 C18 1.3900 .
C16 C18 1.60(2) 8_565
C18 C17 1.3900 .
C17 N4 1.3900 .
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
O1W H1WA O2 0.895(19) 1.82(2) 2.703(5) 167(6) 2_655
