#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/73/4337353.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_4337353
loop_
_publ_author_name
'Pal, Amlan K.'
'Nag, Samik'
'Ferreira, Janaina G.'
'Brochery, Victor'
'La Ganga, Giuseppina'
'Santoro, Antonio'
'Serroni, Scolastica'
'Campagna, Sebastiano'
'Hanan, Garry S.'
_publ_section_title
;
 Red-Emitting [Ru(bpy)2(N-N)](2+) Photosensitizers: Emission from a
 Ruthenium(II) to 2,2'-Bipyridine (3)MLCT State in the Presence of Neutral
 Ancillary "Super Donor" Ligands.
;
_journal_issue                   3
_journal_name_full               'Inorganic chemistry'
_journal_page_first              1679
_journal_page_last               1689
_journal_paper_doi               10.1021/ic4028332
_journal_volume                  53
_journal_year                    2014
_chemical_formula_moiety         'C12 H15 Br N4'
_chemical_formula_sum            'C12 H15 Br N4'
_chemical_formula_weight         295.19
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 92.255(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.0181(2)
_cell_length_b                   18.1139(6)
_cell_length_c                   13.0979(4)
_cell_measurement_reflns_used    3009
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.34
_cell_measurement_theta_min      4.17
_cell_volume                     1189.64(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0689
_diffrn_reflns_av_sigmaI/netI    0.0487
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7559
_diffrn_reflns_theta_full        70.95
_diffrn_reflns_theta_max         70.95
_diffrn_reflns_theta_min         4.17
_exptl_absorpt_coefficient_mu    4.566
_exptl_absorpt_correction_T_max  0.9558
_exptl_absorpt_correction_T_min  0.5882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker (Scale, Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_density_meas      1.648
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.936
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2237
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0366
_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)+(0.0583P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0950
_reflns_number_gt                1898
_reflns_number_total             2237
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic4028332_si_002.cif
_cod_data_source_block           amln41
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_Hall     -P2yn
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4337353
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.98550(6) 0.486372(17) 0.36050(2) 0.02169(14) Uani 1 1 d .
N1 N 0.1795(5) 0.23846(13) 0.12848(18) 0.0186(5) Uani 1 1 d .
N2 N -0.0059(5) 0.25355(14) -0.04065(18) 0.0199(5) Uani 1 1 d .
N3 N 0.2346(5) 0.34956(13) 0.04408(18) 0.0175(5) Uani 1 1 d .
N4 N 0.3863(5) 0.44857(13) 0.14283(19) 0.0193(5) Uani 1 1 d .
C1 C 0.1322(5) 0.27697(16) 0.0476(2) 0.0165(6) Uani 1 1 d .
C2 C 0.0793(6) 0.16298(17) 0.1321(2) 0.0227(6) Uani 1 1 d .
H2A H -0.0909 0.1627 0.1678 0.027 Uiso 1 1 calc R
H2B H 0.2085 0.1323 0.1723 0.027 Uiso 1 1 calc R
C3 C 0.0336(6) 0.12860(16) 0.0269(2) 0.0225(6) Uani 1 1 d .
H3A H 0.2065 0.1198 -0.0049 0.027 Uiso 1 1 calc R
H3B H -0.0596 0.0807 0.0328 0.027 Uiso 1 1 calc R
C4 C -0.1340(6) 0.18129(17) -0.0379(2) 0.0220(6) Uani 1 1 d .
H4A H -0.1568 0.1616 -0.1082 0.026 Uiso 1 1 calc R
H4B H -0.3127 0.1862 -0.0092 0.026 Uiso 1 1 calc R
C5 C -0.1378(6) 0.30471(17) -0.1128(2) 0.0242(6) Uani 1 1 d .
H5A H -0.3144 0.3187 -0.0876 0.029 Uiso 1 1 calc R
H5B H -0.1661 0.2802 -0.1799 0.029 Uiso 1 1 calc R
C6 C 0.0290(6) 0.37271(17) -0.1247(2) 0.0239(6) Uani 1 1 d .
H6A H -0.0705 0.4094 -0.1674 0.029 Uiso 1 1 calc R
H6B H 0.1947 0.3599 -0.1594 0.029 Uiso 1 1 calc R
C7 C 0.0980(6) 0.40542(17) -0.0207(2) 0.0229(6) Uani 1 1 d .
H7A H 0.2152 0.4489 -0.0281 0.027 Uiso 1 1 calc R
H7B H -0.0669 0.4219 0.0117 0.027 Uiso 1 1 calc R
C8 C 0.4116(6) 0.37645(16) 0.1219(2) 0.0173(6) Uani 1 1 d .
C9 C 0.5592(6) 0.47864(16) 0.2119(2) 0.0202(6) Uani 1 1 d .
H9 H 0.5434 0.5297 0.2271 0.024 Uiso 1 1 calc R
C10 C 0.7570(6) 0.43895(17) 0.2614(2) 0.0185(6) Uani 1 1 d .
C11 C 0.7877(6) 0.36443(18) 0.2387(2) 0.0215(6) Uani 1 1 d .
H11 H 0.9265 0.3362 0.2711 0.026 Uiso 1 1 calc R
C12 C 0.6127(6) 0.33264(16) 0.1684(2) 0.0201(6) Uani 1 1 d .
H12 H 0.6276 0.2818 0.1515 0.024 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
C1 N1 C2 118.9(2)
C1 N2 C4 117.3(2)
C1 N2 C5 122.8(2)
C4 N2 C5 113.3(2)
C8 N3 C1 121.1(2)
C8 N3 C7 116.4(2)
C1 N3 C7 119.8(2)
C8 N4 C9 117.9(3)
N1 C1 N2 126.2(3)
N1 C1 N3 118.5(2)
N2 C1 N3 115.2(2)
N1 C2 C3 113.2(2)
N1 C2 H2A 108.9
C3 C2 H2A 108.9
N1 C2 H2B 108.9
C3 C2 H2B 108.9
H2A C2 H2B 107.7
C4 C3 C2 108.1(2)
C4 C3 H3A 110.1
C2 C3 H3A 110.1
C4 C3 H3B 110.1
C2 C3 H3B 110.1
H3A C3 H3B 108.4
N2 C4 C3 110.2(2)
N2 C4 H4A 109.6
C3 C4 H4A 109.6
N2 C4 H4B 109.6
C3 C4 H4B 109.6
H4A C4 H4B 108.1
N2 C5 C6 110.3(2)
N2 C5 H5A 109.6
C6 C5 H5A 109.6
N2 C5 H5B 109.6
C6 C5 H5B 109.6
H5A C5 H5B 108.1
C5 C6 C7 109.6(2)
C5 C6 H6A 109.7
C7 C6 H6A 109.7
C5 C6 H6B 109.7
C7 C6 H6B 109.7
H6A C6 H6B 108.2
N3 C7 C6 109.5(2)
N3 C7 H7A 109.8
C6 C7 H7A 109.8
N3 C7 H7B 109.8
C6 C7 H7B 109.8
H7A C7 H7B 108.2
N4 C8 C12 122.2(3)
N4 C8 N3 114.9(3)
C12 C8 N3 122.6(3)
N4 C9 C10 122.9(3)
N4 C9 H9 118.6
C10 C9 H9 118.6
C9 C10 C11 119.5(3)
C9 C10 Br1 119.5(2)
C11 C10 Br1 121.0(2)
C12 C11 C10 118.4(3)
C12 C11 H11 120.8
C10 C11 H11 120.8
C11 C12 C8 118.9(3)
C11 C12 H12 120.5
C8 C12 H12 120.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C10 1.903(3)
N1 C1 1.283(4)
N1 C2 1.458(4)
N2 C1 1.391(4)
N2 C4 1.459(4)
N2 C5 1.463(4)
N3 C8 1.412(4)
N3 C1 1.413(4)
N3 C7 1.472(4)
N4 C8 1.342(4)
N4 C9 1.344(4)
C2 C3 1.521(4)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.510(4)
C3 H3A 0.9900
C3 H3B 0.9900
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.501(4)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.514(4)
C6 H6A 0.9900
C6 H6B 0.9900
C7 H7A 0.9900
C7 H7B 0.9900
C8 C12 1.404(4)
C9 C10 1.368(4)
C9 H9 0.9500
C10 C11 1.392(4)
C11 C12 1.373(4)
C11 H11 0.9500
C12 H12 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
C2 N1 C1 N2 -0.9(4)
C2 N1 C1 N3 -178.8(3)
C4 N2 C1 N1 6.9(4)
C5 N2 C1 N1 156.5(3)
C4 N2 C1 N3 -175.2(2)
C5 N2 C1 N3 -25.6(4)
C8 N3 C1 N1 7.6(4)
C7 N3 C1 N1 -153.0(3)
C8 N3 C1 N2 -170.5(2)
C7 N3 C1 N2 29.0(4)
C1 N1 C2 C3 24.3(4)
N1 C2 C3 C4 -51.1(3)
C1 N2 C4 C3 -35.3(4)
C5 N2 C4 C3 172.3(3)
C2 C3 C4 N2 55.7(3)
C1 N2 C5 C6 38.9(4)
C4 N2 C5 C6 -170.4(3)
N2 C5 C6 C7 -53.0(3)
C8 N3 C7 C6 152.9(2)
C1 N3 C7 C6 -45.7(4)
C5 C6 C7 N3 56.7(3)
C9 N4 C8 C12 -0.9(4)
C9 N4 C8 N3 -176.2(2)
C1 N3 C8 N4 -146.0(3)
C7 N3 C8 N4 15.2(4)
C1 N3 C8 C12 38.7(4)
C7 N3 C8 C12 -160.1(3)
C8 N4 C9 C10 -0.3(4)
N4 C9 C10 C11 1.4(5)
N4 C9 C10 Br1 -178.4(2)
C9 C10 C11 C12 -1.5(4)
Br1 C10 C11 C12 178.3(2)
C10 C11 C12 C8 0.4(4)
N4 C8 C12 C11 0.8(4)
N3 C8 C12 C11 175.7(3)
