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#$Date: 2016-03-26 02:40:04 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180150 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/47/7104725.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_7104725
loop_
_publ_author_name
'Fu, Wen-Fu'
'Li, Huifang-Jie'
'Wang, De-Hui'
'Zhou, Liang-Jun'
'Li, Li'
'Gan, Xin'
'Xu, Quan-Qing'
'Song, Hai-Bin'
_publ_section_title
;
 A novel Kolbe reaction pathway for a selective one- and two-electron
 reduction of azo compounds.
;
_journal_issue                   37
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              5524
_journal_page_last               5526
_journal_paper_doi               10.1039/b906910k
_journal_volume                  34
_journal_year                    2009
_chemical_formula_sum            'C11 H11 Cl3 N3'
_chemical_formula_weight         291.58
_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 or difmap'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.07(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3383(15)
_cell_length_b                   22.678(5)
_cell_length_c                   8.0867(16)
_cell_measurement_reflns_used    6437
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      2.68
_cell_volume                     1340.5(5)
_computing_cell_refinement       Rapid-AUTO
_computing_data_collection       'Rapid-AUTO (Rigaku,2000)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC,2000)'
_computing_molecular_graphics    'Siemens SHELXTL V4.2,(Sheldrick,1990)'
_computing_publication_material  SHELXL-97,(Sheldrick,1997)
_computing_structure_refinement  SHELXL-97,(Sheldrick,1997)
_computing_structure_solution    SHELXS-97,(Sheldrick,1997)
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Rigaku RAXIS RAPID IP'
_diffrn_measurement_method       Ω
_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  0.0347
_diffrn_reflns_av_sigmaI/netI    0.1118
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6437
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.68
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_correction_T_min  0.767
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
HIGASHI, T. (1995). Abscor-Empirical
Absorption Correction based on Fourier
Series Approximation.
Rigaku Corporation,Tokyo,Japan.
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0040(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.931
_refine_ls_R_factor_all          0.1689
_refine_ls_R_factor_gt           0.0551
_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)+(0.0500P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1399
_reflns_number_gt                766
_reflns_number_total             2318
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b906910k.txt
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7104725
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.0492(4) -0.26664(9) 0.9379(3) 0.2367(15) Uani 1 1 d . . .
Cl2 Cl 0.3244(4) -0.26226(9) 0.8728(3) 0.2202(13) Uani 1 1 d . . .
Cl3 Cl 0.0773(3) -0.32799(8) 0.6630(2) 0.1615(10) Uani 1 1 d . . .
N1 N 0.7193(4) -0.06611(15) 0.5171(4) 0.0536(9) Uani 1 1 d . . .
N2 N 0.6351(4) -0.01681(14) 0.2740(4) 0.0491(9) Uani 1 1 d . . .
HN2 H 0.5661 -0.0450 0.2225 0.093 Uiso 1 1 d . . .
N3 N 0.5283(5) 0.02816(12) 0.0183(4) 0.0539(10) Uani 1 1 d . . .
C1 C 0.7110(5) -0.0141(2) 0.4350(5) 0.0486(11) Uani 1 1 d . . .
C2 C 0.7717(5) 0.04025(19) 0.5014(5) 0.0509(11) Uani 1 1 d . . .
C3 C 0.8453(5) 0.0399(2) 0.6701(5) 0.0594(13) Uani 1 1 d . . .
C4 C 0.8500(6) -0.0136(3) 0.7519(5) 0.0679(14) Uani 1 1 d . . .
H4 H 0.8952 -0.0149 0.8629 0.082 Uiso 1 1 calc R . .
C5 C 0.7903(6) -0.0654(2) 0.6749(5) 0.0592(12) Uani 1 1 d . . .
C6 C 0.7547(5) 0.09080(18) 0.3949(5) 0.0541(12) Uani 1 1 d . . .
H6 H 0.7958 0.1273 0.4348 0.065 Uiso 1 1 calc R . .
C7 C 0.6807(5) 0.08586(19) 0.2402(5) 0.0589(12) Uani 1 1 d . . .
H7 H 0.6744 0.1192 0.1729 0.071 Uiso 1 1 calc R . .
C8 C 0.6096(5) 0.03107(18) 0.1716(5) 0.0490(11) Uani 1 1 d . . .
C9 C 0.8008(6) -0.1221(2) 0.7668(5) 0.0840(16) Uani 1 1 d . . .
H9A H 0.7527 -0.1532 0.6950 0.126 Uiso 1 1 calc R . .
H9B H 0.7303 -0.1193 0.8610 0.126 Uiso 1 1 calc R . .
H9C H 0.9260 -0.1305 0.8037 0.126 Uiso 1 1 calc R . .
C10 C 0.9121(7) 0.0953(2) 0.7577(5) 0.0858(15) Uani 1 1 d . . .
H10A H 0.8978 0.1280 0.6823 0.129 Uiso 1 1 calc R . .
H10B H 1.0389 0.0910 0.7962 0.129 Uiso 1 1 calc R . .
H10C H 0.8422 0.1024 0.8506 0.129 Uiso 1 1 calc R . .
C11 C 0.1301(8) -0.3036(2) 0.8616(6) 0.111(2) Uani 1 1 d . . .
H11 H 0.1554 -0.3385 0.9316 0.134 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'
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'
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
C5 N1 C1 117.1(4) . . ?
C8 N2 C1 124.2(4) . . ?
C8 N2 HN2 104.1(3) . . ?
C1 N2 HN2 129.7(4) . . ?
C8 N3 N3 110.5(4) . 3_655 ?
N1 C1 N2 115.1(4) . . ?
N1 C1 C2 125.5(3) . . ?
N2 C1 C2 119.4(4) . . ?
C1 C2 C3 116.3(4) . . ?
C1 C2 C6 117.8(4) . . ?
C3 C2 C6 125.9(4) . . ?
C4 C3 C2 117.1(4) . . ?
C4 C3 C10 121.1(4) . . ?
C2 C3 C10 121.9(5) . . ?
C3 C4 C5 122.5(4) . . ?
C3 C4 H4 118.7 . . ?
C5 C4 H4 118.7 . . ?
N1 C5 C4 121.5(4) . . ?
N1 C5 C9 117.8(4) . . ?
C4 C5 C9 120.7(4) . . ?
C7 C6 C2 120.5(4) . . ?
C7 C6 H6 119.8 . . ?
C2 C6 H6 119.8 . . ?
C6 C7 C8 122.8(4) . . ?
C6 C7 H7 118.6 . . ?
C8 C7 H7 118.6 . . ?
N3 C8 N2 123.4(4) . . ?
N3 C8 C7 121.3(4) . . ?
N2 C8 C7 115.3(3) . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
Cl2 C11 Cl3 110.3(3) . . ?
Cl2 C11 Cl1 112.1(3) . . ?
Cl3 C11 Cl1 112.2(3) . . ?
Cl2 C11 H11 107.3 . . ?
Cl3 C11 H11 107.3 . . ?
Cl1 C11 H11 107.3 . . ?
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
Cl1 C11 1.720(6) . ?
Cl2 C11 1.702(6) . ?
Cl3 C11 1.711(5) . ?
N1 C5 1.335(5) . ?
N1 C1 1.351(5) . ?
N2 C8 1.368(4) . ?
N2 C1 1.372(4) . ?
N2 HN2 0.894(3) . ?
N3 C8 1.329(4) . ?
N3 N3 1.367(6) 3_655 ?
C1 C2 1.402(5) . ?
C2 C3 1.422(5) . ?
C2 C6 1.433(5) . ?
C3 C4 1.382(6) . ?
C3 C10 1.503(5) . ?
C4 C5 1.382(6) . ?
C4 H4 0.9300 . ?
C5 C9 1.483(6) . ?
C6 C7 1.324(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.439(5) . ?
C7 H7 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11 0.9800 . ?
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
N2 HN2 N3 0.894(3) 2.045(3) 2.567(4) 116.1(2) 3_655
N2 HN2 Cl3 0.894(3) 2.923(2) 3.648(4) 139.3(2) 4_655
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 N2 -179.2(4) . . . . ?
C5 N1 C1 C2 0.4(6) . . . . ?
C8 N2 C1 N1 178.1(3) . . . . ?
C8 N2 C1 C2 -1.6(5) . . . . ?
N1 C1 C2 C3 -1.0(6) . . . . ?
N2 C1 C2 C3 178.7(4) . . . . ?
N1 C1 C2 C6 179.0(4) . . . . ?
N2 C1 C2 C6 -1.3(5) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
C6 C2 C3 C4 -179.9(4) . . . . ?
C1 C2 C3 C10 -178.8(4) . . . . ?
C6 C2 C3 C10 1.2(6) . . . . ?
C2 C3 C4 C5 1.3(6) . . . . ?
C10 C3 C4 C5 -179.8(4) . . . . ?
C1 N1 C5 C4 1.0(6) . . . . ?
C1 N1 C5 C9 -179.9(4) . . . . ?
C3 C4 C5 N1 -1.9(7) . . . . ?
C3 C4 C5 C9 179.0(4) . . . . ?
C1 C2 C6 C7 1.2(6) . . . . ?
C3 C2 C6 C7 -178.8(4) . . . . ?
C2 C6 C7 C8 1.8(6) . . . . ?
N3 N3 C8 N2 1.5(6) 3_655 . . . ?
N3 N3 C8 C7 -179.7(4) 3_655 . . . ?
C1 N2 C8 N3 -176.8(4) . . . . ?
C1 N2 C8 C7 4.3(5) . . . . ?
C6 C7 C8 N3 176.7(4) . . . . ?
C6 C7 C8 N2 -4.4(6) . . . . ?
