#------------------------------------------------------------------------------
#$Date: 2016-05-06 04:33:53 +0300 (Fri, 06 May 2016) $
#$Revision: 182712 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/86/7038687.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_7038687
loop_
_publ_author_name
'Kottelat, E.'
'Ruggi, A.'
'Zobi, F.'
_publ_section_title
;
 Red-light activated photoCORMs of Mn(i) species bearing electron
 deficient 2,2'-azopyridines.
;
_journal_issue                   16
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              6920
_journal_page_last               6927
_journal_paper_doi               10.1039/c6dt00858e
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety         'C10 H6 Br2 N4'
_chemical_formula_sum            'C10 H6 Br2 N4'
_chemical_formula_weight         342.01
_chemical_name_systematic        (E)-1,2-bis(4-bromopyridin-2-yl)diazene
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/cc1kk9s6
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-01-11 deposited with the CCDC.
2016-03-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.821(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.9747(3)
_cell_length_b                   9.2426(11)
_cell_length_c                   14.9310(14)
_cell_measurement_reflns_used    7399
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      25.43
_cell_measurement_theta_min      2.20
_cell_volume                     545.69(9)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2009)'
_computing_data_collection       'X-Area (Stoe & Cie, 2009)'
_computing_data_reduction        'X-RED32(Stoe & Cie, 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      300(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1061
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6662
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.985
_diffrn_reflns_theta_max         24.985
_diffrn_reflns_theta_min         2.595
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    7.402
_exptl_absorpt_correction_T_max  0.8404
_exptl_absorpt_correction_T_min  0.1446
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
Stoe & Cie (2002). X-SHAPE. Stoe & Cie, Darmstadt, Germany
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    2.081
_exptl_crystal_description       needle
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         952
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0322
_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)+(0.0200P)²+0.1933P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0732
_reflns_Friedel_coverage         0.000
_reflns_number_gt                803
_reflns_number_total             952
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6dt00858e2.cif
_cod_data_source_block           EK210
_cod_depositor_comments
'Adding full bibliography for 7038683--7038687.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7038687
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.147
_shelx_estimated_absorpt_t_max   0.589
_shelx_res_file
;

    shelx.res created by SHELXL-2014/7

TITL 210 in P21/n                     New: P21/n
CELL  0.71073   3.9747   9.2426  14.9310   90.000   95.821   90.000
ZERR     2.00   0.0003   0.0011   0.0014    0.000    0.007    0.000
LATT   1
SYMM  1/2 - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    BR   N
UNIT  20 12 4 8
MERG   2
OMIT     0.00  50.00
FMAP   2
PLAN    5
SIZE     0.080   0.120   0.420
ACTA
BOND   $H
CONF
L.S.  20
TEMP    27.00
WGHT    0.020000    0.193300
FVAR       0.73146
BR1   3    0.387374    0.243292    0.314744    11.00000    0.05587    0.04684 =
         0.02953    0.00501    0.01117   -0.00367
N1    4    0.714850    0.209207    0.023589    11.00000    0.05557    0.04149 =
         0.03059   -0.00336    0.00729    0.00217
N2    4    0.572152    0.445875   -0.011047    11.00000    0.06202    0.04137 =
         0.02794    0.00427    0.01041    0.00420
C1    1    0.734592    0.097407    0.081018    11.00000    0.05863    0.03892 =
         0.03657   -0.00317    0.00682    0.00579
AFIX  43
H1    2    0.817713    0.010240    0.061272    11.00000   -1.20000
AFIX   0
C2    1    0.641135    0.102461    0.166602    11.00000    0.04824    0.03471 =
         0.03718    0.00512    0.00149    0.00114
AFIX  43
H2    2    0.662721    0.021478    0.203707    11.00000   -1.20000
AFIX   0
C3    1    0.514174    0.230425    0.196579    11.00000    0.03782    0.04257 =
         0.02816   -0.00094    0.00383   -0.00398
C4    1    0.485647    0.349008    0.139199    11.00000    0.04599    0.03582 =
         0.02811    0.00125    0.00348    0.00085
AFIX  43
H4    2    0.401611    0.437069    0.157247    11.00000   -1.20000
AFIX   0
C5    1    0.587140    0.330659    0.054385    11.00000    0.04745    0.03879 =
         0.02580    0.00331    0.00399   -0.00191
HKLF    4  1.0  0.50  0.00  0.00  0.00 -1.00  0.00 -0.50  0.00 -1.00

REM  210 in P21/n                     New: P21/n
REM R1 =  0.0322 for     803 Fo > 4sig(Fo)  and  0.0401 for all     952 data
REM     73 parameters refined using      0 restraints

END

WGHT      0.0181      0.2234

REM Highest difference peak  0.445,  deepest hole -0.401,  1-sigma level  0.082
Q1    1   0.5183  0.1553  0.3190  11.00000  0.05    0.44
Q2    1   0.2429  0.1610  0.3031  11.00000  0.05    0.42
Q3    1   0.2145  0.3383  0.3031  11.00000  0.05    0.42
Q4    1   0.6100  0.3458  0.3317  11.00000  0.05    0.38
Q5    1   0.7113  0.1963  0.0591  11.00000  0.05    0.23
;
_shelx_res_checksum              3678
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Br1 Br 0.38737(10) 0.24329(4) 0.31474(3) 0.04362(19) Uani 1 1 d . .
N1 N 0.7149(9) 0.2092(3) 0.0236(2) 0.0423(8) Uani 1 1 d . .
N2 N 0.5722(9) 0.4459(3) -0.0110(2) 0.0434(8) Uani 1 1 d . .
C1 C 0.7346(10) 0.0974(4) 0.0810(3) 0.0446(9) Uani 1 1 d . .
H1 H 0.8177 0.0102 0.0613 0.053 Uiso 1 1 calc R U
C2 C 0.6411(9) 0.1025(4) 0.1666(3) 0.0402(9) Uani 1 1 d . .
H2 H 0.6627 0.0215 0.2037 0.048 Uiso 1 1 calc R U
C3 C 0.5142(10) 0.2304(3) 0.1966(3) 0.0361(8) Uani 1 1 d . .
C4 C 0.4856(9) 0.3490(4) 0.1392(2) 0.0367(8) Uani 1 1 d . .
H4 H 0.4016 0.4371 0.1572 0.044 Uiso 1 1 calc R U
C5 C 0.5871(10) 0.3307(4) 0.0544(2) 0.0373(8) Uani 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
Br1 0.0559(3) 0.0468(3) 0.0295(3) 0.00501(16) 0.0112(2) -0.00367(17)
N1 0.056(2) 0.0415(16) 0.0306(18) -0.0034(14) 0.0073(16) 0.0022(14)
N2 0.062(2) 0.0414(16) 0.0279(17) 0.0043(13) 0.0104(15) 0.0042(14)
C1 0.059(3) 0.0389(19) 0.037(2) -0.0032(16) 0.0068(19) 0.0058(16)
C2 0.048(2) 0.0347(17) 0.037(2) 0.0051(15) 0.0015(18) 0.0011(15)
C3 0.038(2) 0.0426(19) 0.028(2) -0.0009(14) 0.0038(17) -0.0040(14)
C4 0.046(2) 0.0358(18) 0.028(2) 0.0012(15) 0.0035(17) 0.0008(14)
C5 0.047(2) 0.039(2) 0.0258(19) 0.0033(15) 0.0040(17) -0.0019(15)
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'
Br Br -0.2901 2.4595 '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
C5 N1 C1 115.4(3) .
N2 N2 C5 114.3(4) 3_665
N1 C1 C2 124.6(4) .
N1 C1 H1 117.7 .
C2 C1 H1 117.7 .
C1 C2 C3 118.4(3) .
C1 C2 H2 120.8 .
C3 C2 H2 120.8 .
C2 C3 C4 119.1(4) .
C2 C3 Br1 119.9(3) .
C4 C3 Br1 120.9(3) .
C5 C4 C3 117.2(3) .
C5 C4 H4 121.4 .
C3 C4 H4 121.4 .
N1 C5 C4 125.3(3) .
N1 C5 N2 112.3(3) .
C4 C5 N2 122.4(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C3 1.887(4) .
N1 C5 1.333(5) .
N1 C1 1.340(5) .
N2 N2 1.215(6) 3_665
N2 C5 1.442(5) .
C1 C2 1.367(5) .
C1 H1 0.9300 .
C2 C3 1.378(5) .
C2 H2 0.9300 .
C3 C4 1.389(5) .
C4 C5 1.378(5) .
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
_geom_torsion_site_symmetry_1
C5 N1 C1 C2 -1.4(6) .
N1 C1 C2 C3 0.7(6) .
C1 C2 C3 C4 0.0(6) .
C1 C2 C3 Br1 -179.2(3) .
C2 C3 C4 C5 0.2(6) .
Br1 C3 C4 C5 179.3(3) .
C1 N1 C5 C4 1.7(6) .
C1 N1 C5 N2 -179.7(4) .
C3 C4 C5 N1 -1.1(6) .
C3 C4 C5 N2 -179.5(3) .
N2 N2 C5 N1 173.3(4) 3_665
N2 N2 C5 C4 -8.0(7) 3_665
