#------------------------------------------------------------------------------
#$Date: 2016-08-06 09:20:25 +0300 (Sat, 06 Aug 2016) $
#$Revision: 185055 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/01/7040172.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_7040172
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         'Cl, C12 H11 N6'
_chemical_formula_sum            'C12 H11 Cl N6'
_chemical_formula_weight         274.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_update_record
;
2016-03-31 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 119.39(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.984(5)
_cell_length_b                   3.8567(8)
_cell_length_c                   14.587(3)
_cell_measurement_reflns_used    2626
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.113
_cell_measurement_theta_min      2.802
_cell_volume                     1273.7(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7849
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.960
_diffrn_reflns_theta_min         1.799
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.295
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0561 before and 0.0473 after correction.
The Ratio of minimum to maximum transmission is 0.8914.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.569
_exptl_crystal_size_mid          0.359
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1403
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.089
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0329
_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)+(0.0335P)²+1.3917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0775
_refine_ls_wR_factor_ref         0.0822
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1202
_reflns_number_total             1403
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6dt01597b2.cif
_cod_data_source_block           test
_cod_original_cell_volume        1273.6(6)
_cod_database_code               7040172
_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. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Others
 Fixed Sof: H3(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C5(H5), C3(H3A), C4(H4)
;
_shelx_res_file
;
    test.res created by SHELXL-2014/7

TITL test_a.res in C2/c
REM Old TITL test in Cc #9
REM SHELXT solution in C2/c
REM R1 0.091, Rweak 0.002, Alpha 0.020, Orientation as input
REM Formula found by SHELXT: C12 N6 Cl
CELL 0.71073 25.984 3.8567 14.5866 90 119.389 90
ZERR 4 0.0052 0.0008 0.0029 0 0.03 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H Cl N
UNIT 48 44 4 24

L.S. 10
PLAN  -5
TEMP 100
BOND $H
LIST 4
MORE -1
CONF
fmap 2
acta 52
REM <olex2.extras>
REM <HklSrc "%.\\test.hkl">
REM </olex2.extras>

WGHT    0.033500    1.391700
FVAR       0.46944
CL1   3    0.500000    0.118233    0.250000    10.50000    0.01544    0.01325 =
         0.01906    0.00000    0.00405    0.00000
N1    4    0.605591    0.550089    0.397573    11.00000    0.01549    0.01682 =
         0.01670    0.00108    0.00313   -0.00097
N3    4    0.695325    0.706409    0.483276    11.00000    0.02057    0.01791 =
         0.01943    0.00048    0.01165   -0.00098
AFIX  43
H3    2    0.731712    0.740071    0.500687    10.50000   -1.20000
AFIX   0
N2    4    0.656164    0.550977    0.396480    11.00000    0.02569    0.01872 =
         0.01850    0.00101    0.01093    0.00032
C6    1    0.610938    0.704038    0.485709    11.00000    0.01543    0.01197 =
         0.01716    0.00428    0.00613    0.00134
C1    1    0.669812    0.806842    0.541884    11.00000    0.01663    0.01322 =
         0.01612    0.00355    0.00862    0.00161
C2    1    0.692656    0.974379    0.639439    11.00000    0.02036    0.01562 =
         0.01730    0.00121    0.00579    0.00077
AFIX  43
H2    2    0.731762    1.047262    0.676715    11.00000   -1.20000
AFIX   0
C5    1    0.571330    0.763027    0.523219    11.00000    0.01612    0.01990 =
         0.03215    0.00967    0.01299    0.00411
AFIX  43
H5    2    0.531795    0.699044    0.484999    11.00000   -1.20000
AFIX   0
C3    1    0.653964    1.024364    0.676601    11.00000    0.03682    0.01865 =
         0.01923    0.00259    0.01568    0.00653
AFIX  43
H3A   2    0.667480    1.130400    0.741698    11.00000   -1.20000
AFIX   0
C4    1    0.594281    0.920371    0.619429    11.00000    0.03378    0.02324 =
         0.03428    0.01001    0.02636    0.01103
AFIX  43
H4    2    0.569768    0.960073    0.648073    11.00000   -1.20000
AFIX   0
H1    2    0.573459    0.450978    0.344157    11.00000    0.04157
HKLF 4

REM  test_a.res in C2/c
REM R1 =  0.0329 for    1202 Fo > 4sig(Fo)  and  0.0407 for all    1403 data
REM     91 parameters refined using      0 restraints

END

WGHT      0.0334      1.3918

REM Highest difference peak  0.344,  deepest hole -0.201,  1-sigma level  0.058
Q1    1   0.6376  0.7906  0.5128  11.00000  0.05    0.34
Q2    1   0.5405  0.1477  0.3137  11.00000  0.05    0.28
Q3    1   0.6816  0.7439  0.5222  11.00000  0.05    0.27
Q4    1   0.5949  0.6926  0.5112  11.00000  0.05    0.26
Q5    1   0.6836  0.8558  0.5872  11.00000  0.05    0.23
;
_shelx_res_checksum              96905
_shelx_shelxl_version_number     2014/7
_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'
'-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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Cl1 Cl 0.5000 0.11823(13) 0.2500 0.01782(16) Uani 1 2 d S T P
N1 N 0.60559(6) 0.5501(3) 0.39757(10) 0.0184(3) Uani 1 1 d . . .
N3 N 0.69533(6) 0.7064(3) 0.48328(10) 0.0185(3) Uani 1 1 d . . .
H3 H 0.7317 0.7401 0.5007 0.022 Uiso 0.5 1 calc R . .
N2 N 0.65616(6) 0.5510(3) 0.39648(10) 0.0209(3) Uani 1 1 d . . .
C6 C 0.61094(6) 0.7040(4) 0.48571(11) 0.0157(3) Uani 1 1 d . . .
C1 C 0.66981(6) 0.8068(4) 0.54188(11) 0.0151(3) Uani 1 1 d . . .
C2 C 0.69266(7) 0.9744(4) 0.63944(12) 0.0192(3) Uani 1 1 d . . .
H2 H 0.7318 1.0473 0.6767 0.023 Uiso 1 1 calc R . .
C5 C 0.57133(7) 0.7630(4) 0.52322(13) 0.0222(4) Uani 1 1 d . . .
H5 H 0.5318 0.6990 0.4850 0.027 Uiso 1 1 calc R . .
C3 C 0.65396(8) 1.0244(4) 0.67660(13) 0.0241(4) Uani 1 1 d . . .
H3A H 0.6675 1.1304 0.7417 0.029 Uiso 1 1 calc R . .
C4 C 0.59428(8) 0.9204(4) 0.61943(13) 0.0263(4) Uani 1 1 d . . .
H4 H 0.5698 0.9601 0.6481 0.032 Uiso 1 1 calc R . .
H1 H 0.5735(9) 0.451(6) 0.3442(16) 0.042(6) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0154(3) 0.0132(3) 0.0191(3) 0.000 0.0041(2) 0.000
N1 0.0155(6) 0.0168(7) 0.0167(6) 0.0011(5) 0.0031(5) -0.0010(5)
N3 0.0206(7) 0.0179(7) 0.0194(6) 0.0005(5) 0.0116(6) -0.0010(5)
N2 0.0257(7) 0.0187(7) 0.0185(6) 0.0010(5) 0.0109(6) 0.0003(6)
C6 0.0154(7) 0.0120(7) 0.0172(7) 0.0043(6) 0.0061(6) 0.0013(6)
C1 0.0166(7) 0.0132(7) 0.0161(7) 0.0035(6) 0.0086(6) 0.0016(6)
C2 0.0204(8) 0.0156(8) 0.0173(7) 0.0012(6) 0.0058(6) 0.0008(6)
C5 0.0161(8) 0.0199(8) 0.0322(9) 0.0097(7) 0.0130(7) 0.0041(6)
C3 0.0368(10) 0.0186(8) 0.0192(8) 0.0026(6) 0.0157(7) 0.0065(7)
C4 0.0338(9) 0.0232(9) 0.0343(9) 0.0100(7) 0.0264(8) 0.0110(7)
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'
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
N2 N1 C6 111.67(13)
N2 N1 H1 119.7(13)
C6 N1 H1 128.6(13)
N2 N3 H3 124.9
N2 N3 C1 110.27(12)
C1 N3 H3 124.9
N3 N2 N1 107.06(12)
N1 C6 C1 104.70(13)
N1 C6 C5 133.33(15)
C1 C6 C5 121.97(14)
N3 C1 C6 106.30(13)
N3 C1 C2 132.08(14)
C6 C1 C2 121.61(13)
C1 C2 H2 122.0
C3 C2 C1 116.04(14)
C3 C2 H2 122.0
C6 C5 H5 122.0
C4 C5 C6 116.02(15)
C4 C5 H5 122.0
C2 C3 H3A 118.9
C2 C3 C4 122.22(15)
C4 C3 H3A 118.9
C5 C4 C3 122.11(15)
C5 C4 H4 118.9
C3 C4 H4 118.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 N2 1.3220(18)
N1 C6 1.360(2)
N1 H1 0.90(2)
N3 H3 0.8600
N3 N2 1.3165(19)
N3 C1 1.3699(19)
C6 C1 1.392(2)
C6 C5 1.401(2)
C1 C2 1.402(2)
C2 H2 0.9300
C2 C3 1.370(2)
C5 H5 0.9300
C5 C4 1.368(2)
C3 H3A 0.9300
C3 C4 1.411(2)
C4 H4 0.9300
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
N1 C6 C1 N3 -0.08(16)
N1 C6 C1 C2 -179.30(14)
N1 C6 C5 C4 177.88(16)
N3 C1 C2 C3 -177.84(15)
N2 N1 C6 C1 0.23(17)
N2 N1 C6 C5 -179.19(16)
N2 N3 C1 C6 -0.10(16)
N2 N3 C1 C2 179.01(16)
C6 N1 N2 N3 -0.30(17)
C6 C1 C2 C3 1.2(2)
C6 C5 C4 C3 1.4(2)
C1 N3 N2 N1 0.25(16)
C1 C6 C5 C4 -1.5(2)
C1 C2 C3 C4 -1.3(2)
C2 C3 C4 C5 0.0(3)
C5 C6 C1 N3 179.43(13)
C5 C6 C1 C2 0.2(2)
