#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:58:52 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180366 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/35/7203557.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_7203557
loop_
_publ_author_name
'Jones, Leigh F.'
'Camm, Kenneth D.'
'Kilner, Colin A.'
'Halcrow, Malcolm A.'
_publ_section_title
;
 Novel hydrogen bond network topologies in complexes of the ditopic
 ligand 5-amino-3-(pyrid-2-yl)-1H-pyrazole
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              719
_journal_paper_doi               10.1039/b609424d
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C16 H16 Cl2 Mn N8, 2[C H4 O]'
_chemical_formula_sum            'C18 H24 Cl2 Mn N8 O2'
_chemical_formula_weight         510.29
_chemical_name_systematic
;
Dichloro-bis[5-amino-3-(pyrid-2-yl)pyrazole]manganese(II)
dimethanol solvate (1.2CH₃OH)
;
_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                 125.6748(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.9615(3)
_cell_length_b                   11.9420(3)
_cell_length_c                   12.8415(2)
_cell_measurement_reflns_used    20264
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.53
_cell_measurement_theta_min      2.64
_cell_volume                     2362.13(8)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEX (McArdle, 1995)'
_computing_publication_material  'local program'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type
'Nonius KappaCCD area detector diffractometer'
_diffrn_measurement_method       'ω and φ 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  0.0898
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20264
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.64
_exptl_absorpt_coefficient_mu    0.816
_exptl_absorpt_correction_T_max  0.816
_exptl_absorpt_correction_T_min  0.536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Using multiple and symmetry-related data measurements via the program SORTAV
See R.H. Blessing, Acta Cryst (1995), A51, 33-38
;
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Rectangular prism'
_exptl_crystal_F_000             1052
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.36
_refine_diff_density_max         1.013
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2711
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0406
_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)+(0.0672P)²+2.7099P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1239
_reflns_number_gt                2382
_reflns_number_total             2711
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b609424d.txt
_cod_data_source_block           c:\datasets\leeds\ljf11b\ljf11b
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        2362.12(8)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7203557
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Mn1 Mn 0.0000 0.31772(4) 0.2500 0.03020(16) Uani 1 2 d S . .
Cl2 Cl 0.07653(3) 0.44972(5) 0.19334(5) 0.03857(17) Uani 1 1 d . . .
N3 N 0.08940(12) 0.16779(15) 0.27955(18) 0.0354(4) Uani 1 1 d . . .
C4 C 0.08073(16) 0.1043(2) 0.1867(2) 0.0452(6) Uani 1 1 d . . .
H4 H 0.0367 0.1228 0.0999 0.054 Uiso 1 1 calc R . .
C5 C 0.1335(2) 0.0127(2) 0.2125(3) 0.0544(7) Uani 1 1 d . . .
H5 H 0.1248 -0.0316 0.1445 0.065 Uiso 1 1 calc R . .
C6 C 0.19874(19) -0.0132(2) 0.3380(3) 0.0533(7) Uani 1 1 d . . .
H6 H 0.2363 -0.0748 0.3575 0.064 Uiso 1 1 calc R . .
C7 C 0.20899(16) 0.05209(19) 0.4359(2) 0.0424(5) Uani 1 1 d . . .
H7 H 0.2535 0.0361 0.5233 0.051 Uiso 1 1 calc R . .
C8 C 0.15243(14) 0.14120(17) 0.4025(2) 0.0332(4) Uani 1 1 d . . .
C9 C 0.15617(13) 0.21269(17) 0.4984(2) 0.0316(4) Uani 1 1 d . . .
N10 N 0.09567(12) 0.29244(15) 0.45528(17) 0.0331(4) Uani 1 1 d . . .
N11 N 0.11238(12) 0.34247(16) 0.56318(18) 0.0353(4) Uani 1 1 d D . .
H11 H 0.0824(19) 0.400(2) 0.560(3) 0.067(5) Uiso 1 1 d D . .
C12 C 0.18132(14) 0.29510(19) 0.6714(2) 0.0355(5) Uani 1 1 d . . .
C13 C 0.21151(14) 0.21040(18) 0.6323(2) 0.0345(4) Uani 1 1 d . . .
H13 H 0.2593 0.1617 0.6851 0.041 Uiso 1 1 calc R . .
N14 N 0.20710(16) 0.3273(2) 0.7899(2) 0.0485(5) Uani 1 1 d D . .
C15 C 0.4290(3) 0.2109(4) 1.0862(3) 0.0822(12) Uani 1 1 d . . .
H15A H 0.4826 0.2495 1.1124 0.123 Uiso 1 1 calc R . .
H15B H 0.4423 0.1332 1.1163 0.123 Uiso 1 1 calc R . .
H15C H 0.4028 0.2490 1.1235 0.123 Uiso 1 1 calc R . .
O16 O 0.37197(16) 0.2123(2) 0.9551(2) 0.0714(6) Uani 1 1 d D . .
H16 H 0.386(2) 0.172(3) 0.907(3) 0.067(5) Uiso 1 1 d D . .
H14A H 0.1924(19) 0.3920(18) 0.791(3) 0.067(5) Uiso 1 1 d D . .
H14B H 0.2583(14) 0.308(3) 0.850(3) 0.067(5) 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'
O O 0.0106 0.0060 '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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N10 Mn1 N10 164.08(10) 2 . ?
N10 Mn1 N3 95.94(7) . 2 ?
N10 Mn1 N3 71.62(7) . . ?
N3 Mn1 N3 80.13(9) 2 . ?
N10 Mn1 Cl2 102.86(5) . . ?
N3 Mn1 Cl2 92.34(5) . . ?
N10 Mn1 Cl2 87.17(5) . 2 ?
N3 Mn1 Cl2 156.44(5) . 2 ?
Cl2 Mn1 Cl2 102.56(3) . 2 ?
C4 N3 C8 118.24(19) . . ?
C4 N3 Mn1 125.98(16) . . ?
C8 N3 Mn1 115.70(14) . . ?
N3 C4 C5 122.5(2) . . ?
N3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
C6 C5 C4 119.2(2) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C7 119.2(2) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C8 C7 C6 118.2(2) . . ?
C8 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
N3 C8 C7 122.7(2) . . ?
N3 C8 C9 114.94(18) . . ?
C7 C8 C9 122.4(2) . . ?
N10 C9 C13 111.74(19) . . ?
N10 C9 C8 117.22(18) . . ?
C13 C9 C8 130.99(19) . . ?
C9 N10 N11 104.84(17) . . ?
C9 N10 Mn1 120.46(14) . . ?
N11 N10 Mn1 134.69(14) . . ?
C12 N11 N10 111.80(18) . . ?
C12 N11 H11 126(2) . . ?
N10 N11 H11 122(2) . . ?
N14 C12 N11 122.2(2) . . ?
N14 C12 C13 131.0(2) . . ?
N11 C12 C13 106.69(19) . . ?
C12 C13 C9 104.93(19) . . ?
C12 C13 H13 127.5 . . ?
C9 C13 H13 127.5 . . ?
C12 N14 H14A 112(2) . . ?
C12 N14 H14B 115(2) . . ?
H14A N14 H14B 117(3) . . ?
O16 C15 H15A 109.5 . . ?
O16 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O16 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C15 O16 H16 118(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mn1 N10 2.1802(18) . ?
Mn1 N3 2.3395(18) . ?
Mn1 Cl2 2.5203(6) . ?
N3 C4 1.339(3) . ?
N3 C8 1.349(3) . ?
C4 C5 1.386(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.377(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.389(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.466(3) . ?
C9 N10 1.337(3) . ?
C9 C13 1.398(3) . ?
N10 N11 1.366(3) . ?
N11 C12 1.357(3) . ?
N11 H11 0.875(18) . ?
C12 N14 1.355(3) . ?
C12 C13 1.392(3) . ?
C13 H13 0.9500 . ?
N14 H14A 0.825(17) . ?
N14 H14B 0.844(17) . ?
C15 O16 1.371(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O16 H16 0.934(18) . ?
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
N11 H11 Cl2 0.875(18) 2.53(2) 3.2771(19) 144(3) 6_566
N14 H14A Cl2 0.825(17) 2.600(19) 3.344(2) 151(3) 6_566
N14 H14B O16 0.844(17) 2.096(18) 2.902(3) 159(3) .
O16 H16 Cl2 0.934(18) 2.312(19) 3.240(3) 172(3) 7_556
