#------------------------------------------------------------------------------
#$Date: 2016-08-06 09:20:25 +0300 (Sat, 06 Aug 2016) $
#$Revision: 185055 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/01/7040171.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_7040171
loop_
_publ_author_name
'Brede, Franziska A.'
'Mühlbach, Friedrich'
'Sextl, Gerhard'
'Müller-Buschbaum, Klaus'
_publ_section_title
;
 Mechanochemical and thermal formation of 1H-benzotriazole coordination
 polymers and complexes of 3d-transition metals with intriguing dielectric
 properties.
;
_journal_issue                   26
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              10609
_journal_page_last               10619
_journal_paper_doi               10.1039/c6dt01597b
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety         'C12 H10 Cl2 Mn N6'
_chemical_formula_sum            'C12 H10 Cl2 Mn N6'
_chemical_formula_weight         364.10
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2016-03-22 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.4285(10)
_cell_length_b                   3.6906(2)
_cell_length_c                   23.2854(14)
_cell_measurement_reflns_used    5366
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.686
_cell_measurement_theta_min      2.629
_cell_volume                     1411.82(14)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 ver. 2014.1 (Bruker AXS)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'Olex2 (Dolomanov et al., 2009)'
_diffrn_ambient_temperature      99.65
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0413
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            19984
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.076
_diffrn_reflns_theta_min         1.749
_exptl_absorpt_coefficient_mu    1.314
_exptl_absorpt_correction_T_max  0.810
_exptl_absorpt_correction_T_min  0.741
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'Twinabs 2014/3 (Bruker 2014)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             732
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.06(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3918
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0345
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0411P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0789
_reflns_Friedel_coverage         0.956
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                3358
_reflns_number_total             3918
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6dt01597b2.cif
_cod_data_source_block           fb-mn-226
_cod_database_code               7040171
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.94(3) 0.06(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C11(H11), C10(H10), N6(H6), C2(H2), C9(H9), C3(H3A), C8(H8), C4(H4),
 C5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
Mn1 Mn 0.62094(3) 0.41968(13) 0.35526(3) 0.00847(12) Uani 1 1 d .
Cl1 Cl 0.56229(5) -0.0788(2) 0.29178(3) 0.00971(19) Uani 1 1 d .
Cl2 Cl 0.67915(5) -0.0805(3) 0.41885(3) 0.00978(19) Uani 1 1 d .
N4 N 0.73633(19) 0.4329(9) 0.30091(14) 0.0093(6) Uani 1 1 d .
N5 N 0.8029(2) 0.5356(10) 0.32817(15) 0.0120(7) Uani 1 1 d .
N3 N 0.37782(18) 0.5548(10) 0.42147(15) 0.0124(7) Uani 1 1 d .
H3 H 0.3274 0.6153 0.4132 0.015 Uiso 1 1 calc R
C1 C 0.4041(2) 0.4579(11) 0.47457(18) 0.0097(7) Uani 1 1 d .
N2 N 0.4384(2) 0.5462(10) 0.38355(15) 0.0109(7) Uani 1 1 d .
C11 C 0.7111(2) 0.2258(12) 0.1984(2) 0.0121(10) Uani 1 1 d .
H11 H 0.6540 0.1902 0.2016 0.014 Uiso 1 1 calc R
C10 C 0.7520(3) 0.1656(13) 0.1475(2) 0.0148(9) Uani 1 1 d .
H10 H 0.7220 0.0909 0.1147 0.018 Uiso 1 1 calc R
N6 N 0.8657(2) 0.5129(9) 0.29170(16) 0.0112(7) Uani 1 1 d .
H6 H 0.9162 0.5693 0.3006 0.013 Uiso 1 1 calc R
C2 C 0.3651(2) 0.4326(11) 0.52848(17) 0.0139(8) Uani 1 1 d .
H2 H 0.3088 0.4822 0.5332 0.017 Uiso 1 1 calc R
C6 C 0.4875(2) 0.3845(10) 0.46693(17) 0.0097(7) Uani 1 1 d .
N1 N 0.50580(19) 0.4447(9) 0.40996(15) 0.0102(7) Uani 1 1 d .
C9 C 0.8374(3) 0.2122(11) 0.1429(2) 0.0138(9) Uani 1 1 d .
H9 H 0.8632 0.1648 0.1072 0.017 Uiso 1 1 calc R
C3 C 0.4135(3) 0.3325(12) 0.5733(2) 0.0146(9) Uani 1 1 d .
H3A H 0.3903 0.3126 0.6105 0.017 Uiso 1 1 calc R
C8 C 0.8836(2) 0.3236(11) 0.18842(18) 0.0130(8) Uani 1 1 d .
H8 H 0.9409 0.3523 0.1854 0.016 Uiso 1 1 calc R
C7 C 0.8419(2) 0.3930(10) 0.23964(17) 0.0093(8) Uani 1 1 d .
C12 C 0.7576(2) 0.3413(11) 0.24509(18) 0.0087(8) Uani 1 1 d .
C4 C 0.4976(3) 0.2572(11) 0.5659(2) 0.0143(9) Uani 1 1 d .
H4 H 0.5286 0.1889 0.5986 0.017 Uiso 1 1 calc R
C5 C 0.5359(3) 0.2786(11) 0.5138(2) 0.0130(10) Uani 1 1 d .
H5 H 0.5921 0.2248 0.5096 0.016 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'
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'
N N 0.0061 0.0033 '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
Cl1 Mn1 Cl1 92.56(3) . 1_565
Cl1 Mn1 Cl2 179.80(4) . 1_565
Cl1 Mn1 Cl2 87.48(3) . .
Cl2 Mn1 Cl1 179.82(4) . 1_565
Cl2 Mn1 Cl1 87.33(3) 1_565 1_565
Cl2 Mn1 Cl2 92.63(3) 1_565 .
N4 Mn1 Cl1 88.68(9) . 1_565
N4 Mn1 Cl1 90.45(9) . .
N4 Mn1 Cl2 89.72(9) . 1_565
N4 Mn1 Cl2 91.49(9) . .
N4 Mn1 N1 176.45(10) . .
N1 Mn1 Cl1 92.26(9) . .
N1 Mn1 Cl1 88.91(9) . 1_565
N1 Mn1 Cl2 87.57(9) . 1_565
N1 Mn1 Cl2 90.92(9) . .
Mn1 Cl1 Mn1 92.56(3) . 1_545
Mn1 Cl2 Mn1 92.63(3) 1_545 .
N5 N4 Mn1 115.3(2) . .
N5 N4 C12 108.2(3) . .
C12 N4 Mn1 136.4(2) . .
N4 N5 N6 108.4(3) . .
C1 N3 H3 124.4 . .
N2 N3 H3 124.4 . .
N2 N3 C1 111.1(3) . .
N3 C1 C2 133.1(4) . .
N3 C1 C6 104.2(3) . .
C6 C1 C2 122.7(4) . .
N1 N2 N3 108.9(3) . .
C10 C11 H11 121.6 . .
C10 C11 C12 116.8(4) . .
C12 C11 H11 121.6 . .
C11 C10 H10 119.1 . .
C11 C10 C9 121.8(4) . .
C9 C10 H10 119.1 . .
N5 N6 H6 124.2 . .
N5 N6 C7 111.6(3) . .
C7 N6 H6 124.2 . .
C1 C2 H2 122.1 . .
C3 C2 C1 115.8(4) . .
C3 C2 H2 122.1 . .
N1 C6 C1 107.7(3) . .
N1 C6 C5 131.9(4) . .
C5 C6 C1 120.4(4) . .
N2 N1 Mn1 116.5(2) . .
N2 N1 C6 108.1(3) . .
C6 N1 Mn1 135.4(3) . .
C10 C9 H9 119.1 . .
C8 C9 C10 121.8(4) . .
C8 C9 H9 119.1 . .
C2 C3 H3A 119.1 . .
C2 C3 C4 121.8(4) . .
C4 C3 H3A 119.1 . .
C9 C8 H8 121.8 . .
C9 C8 C7 116.3(4) . .
C7 C8 H8 121.8 . .
N6 C7 C8 133.2(4) . .
N6 C7 C12 104.4(3) . .
C8 C7 C12 122.4(4) . .
N4 C12 C11 131.7(4) . .
N4 C12 C7 107.5(3) . .
C11 C12 C7 120.8(4) . .
C3 C4 H4 118.5 . .
C5 C4 C3 122.9(4) . .
C5 C4 H4 118.5 . .
C6 C5 H5 121.8 . .
C4 C5 C6 116.4(4) . .
C4 C5 H5 121.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mn1 Cl1 2.5491(11) .
Mn1 Cl1 2.5572(11) 1_565
Mn1 Cl2 2.5515(11) 1_565
Mn1 Cl2 2.5522(11) .
Mn1 N4 2.280(3) .
Mn1 N1 2.282(3) .
Cl1 Mn1 2.5572(11) 1_545
Cl2 Mn1 2.5514(11) 1_545
N4 N5 1.319(5) .
N4 C12 1.388(5) .
N5 N6 1.339(5) .
N3 H3 0.8800 .
N3 C1 1.357(5) .
N3 N2 1.331(5) .
C1 C2 1.412(6) .
C1 C6 1.408(5) .
N2 N1 1.321(5) .
C11 H11 0.9500 .
C11 C10 1.380(7) .
C11 C12 1.395(6) .
C10 H10 0.9500 .
C10 C9 1.418(6) .
N6 H6 0.8800 .
N6 C7 1.348(5) .
C2 H2 0.9500 .
C2 C3 1.363(6) .
C6 N1 1.379(5) .
C6 C5 1.407(6) .
C9 H9 0.9500 .
C9 C8 1.367(6) .
C3 H3A 0.9500 .
C3 C4 1.420(6) .
C8 H8 0.9500 .
C8 C7 1.399(6) .
C7 C12 1.403(5) .
C4 H4 0.9500 .
C4 C5 1.368(7) .
C5 H5 0.9500 .
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
Mn1 N4 N5 N6 177.0(2)
Mn1 N4 C12 C11 5.8(7)
Mn1 N4 C12 C7 -175.8(3)
N4 N5 N6 C7 -0.3(4)
N5 N4 C12 C11 -178.2(5)
N5 N4 C12 C7 0.2(4)
N5 N6 C7 C8 -179.7(4)
N5 N6 C7 C12 0.4(4)
N3 C1 C2 C3 -178.2(4)
N3 C1 C6 N1 0.4(4)
N3 C1 C6 C5 179.2(4)
N3 N2 N1 Mn1 -178.6(3)
N3 N2 N1 C6 0.3(4)
C1 N3 N2 N1 0.0(5)
C1 C2 C3 C4 -0.3(6)
C1 C6 N1 Mn1 178.1(3)
C1 C6 N1 N2 -0.5(4)
C1 C6 C5 C4 -0.8(6)
N2 N3 C1 C2 178.3(4)
N2 N3 C1 C6 -0.3(4)
C11 C10 C9 C8 -0.8(7)
C10 C11 C12 N4 178.3(4)
C10 C11 C12 C7 0.1(6)
C10 C9 C8 C7 -0.7(6)
N6 C7 C12 N4 -0.4(4)
N6 C7 C12 C11 178.2(4)
C2 C1 C6 N1 -178.3(4)
C2 C1 C6 C5 0.4(6)
C2 C3 C4 C5 -0.1(7)
C6 C1 C2 C3 0.1(6)
N1 C6 C5 C4 177.6(4)
C9 C8 C7 N6 -178.0(4)
C9 C8 C7 C12 1.9(6)
C3 C4 C5 C6 0.6(6)
C8 C7 C12 N4 179.7(4)
C8 C7 C12 C11 -1.7(6)
C12 N4 N5 N6 0.1(4)
C12 C11 C10 C9 1.1(7)
C5 C6 N1 Mn1 -0.5(7)
C5 C6 N1 N2 -179.0(4)
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.94(3)
2 0.06(3)
