#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:41:52 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178477 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/98/4029896.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_4029896
loop_
_publ_author_name
'Sadhu, Pradeep'
'Alla, Santhosh Kumar'
'Punniyamurthy, Tharmalingam'
_publ_section_title
;
 Room-Temperature Cu(II)-Catalyzed Chemo- and Regioselective
 Ortho-Nitration of Arenes via C-H Functionalization.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8541
_journal_page_last               8549
_journal_paper_doi               10.1021/jo501617g
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C13 H8 Cl2 N6 O2'
_chemical_formula_weight         351.15
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.507(7)
_cell_angle_beta                 94.517(6)
_cell_angle_gamma                90.802(7)
_cell_formula_units_Z            2
_cell_length_a                   6.4492(5)
_cell_length_b                   7.6732(7)
_cell_length_c                   15.1467(11)
_cell_measurement_temperature    296(2)
_cell_volume                     731.86(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0520
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4634
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.17
_exptl_absorpt_coefficient_mu    0.463
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_correction_T_min  0.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.228
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2572
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.228
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0450
_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)+(0.0100P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0604
_refine_ls_wR_factor_ref         0.0722
_reflns_number_gt                1682
_reflns_number_total             2572
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501617g_si_001.cif
_cod_data_source_block           exp_806
_cod_depositor_comments          'Adding full bibliography for 4029896.cif.'
_cod_original_cell_volume        731.87(10)
_cod_database_code               4029896
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.38447(12) 0.73265(11) 1.16596(4) 0.0668(3) Uani 1 1 d .
Cl2 Cl 0.22052(13) 0.66279(13) 0.36085(4) 0.0774(3) Uani 1 1 d .
O2 O 0.2595(3) 0.5873(3) 0.74485(11) 0.0631(6) Uani 1 1 d .
O1 O 0.0752(3) 0.5004(3) 0.84142(13) 0.0820(8) Uani 1 1 d .
N6 N 0.8010(3) 0.8597(3) 0.68846(13) 0.0443(6) Uani 1 1 d .
N2 N 0.6113(4) 0.7620(3) 0.79748(15) 0.0478(7) Uani 1 1 d .
N1 N 0.2274(4) 0.5803(3) 0.82372(16) 0.0545(7) Uani 1 1 d .
N3 N 0.9545(3) 0.9042(3) 0.82476(14) 0.0545(7) Uani 1 1 d .
N4 N 1.0789(3) 0.9635(4) 0.76682(17) 0.0644(8) Uani 1 1 d .
N5 N 0.9919(3) 0.9392(3) 0.68562(15) 0.0578(7) Uani 1 1 d .
C4 C 0.4516(4) 0.7397(4) 1.05766(16) 0.0461(7) Uani 1 1 d .
C11 C 0.3943(4) 0.7264(4) 0.45563(16) 0.0515(8) Uani 1 1 d .
C7 C 0.7844(4) 0.8404(4) 0.77450(17) 0.0443(7) Uani 1 1 d .
C1 C 0.5604(4) 0.7516(4) 0.88390(16) 0.0409(7) Uani 1 1 d .
C8 C 0.6607(4) 0.8145(4) 0.60867(16) 0.0425(7) Uani 1 1 d .
C2 C 0.6939(4) 0.8224(4) 0.96098(16) 0.0487(8) Uani 1 1 d .
H2 H 0.8211 0.8747 0.9542 0.058 Uiso 1 1 calc R
C6 C 0.3734(4) 0.6700(4) 0.89821(16) 0.0408(7) Uani 1 1 d .
C9 C 0.4609(4) 0.8750(4) 0.60954(16) 0.0472(8) Uani 1 1 d .
H9 H 0.4167 0.9459 0.6615 0.057 Uiso 1 1 calc R
C10 C 0.3263(4) 0.8292(4) 0.53218(16) 0.0490(8) Uani 1 1 d .
H10 H 0.1903 0.8679 0.5321 0.059 Uiso 1 1 calc R
C5 C 0.3181(4) 0.6664(4) 0.98454(17) 0.0465(7) Uani 1 1 d .
H5 H 0.1915 0.6147 0.9926 0.056 Uiso 1 1 calc R
C13 C 0.7305(4) 0.7137(4) 0.53093(17) 0.0522(8) Uani 1 1 d .
H13 H 0.8666 0.6753 0.5306 0.063 Uiso 1 1 calc R
C3 C 0.6397(4) 0.8157(4) 1.04628(17) 0.0520(8) Uani 1 1 d .
H3 H 0.7305 0.8627 1.0964 0.062 Uiso 1 1 calc R
C12 C 0.5959(4) 0.6710(4) 0.45399(17) 0.0562(8) Uani 1 1 d .
H12 H 0.6414 0.6048 0.4011 0.067 Uiso 1 1 calc R
H2A H 0.512(4) 0.718(4) 0.7573(16) 0.068(10) Uiso 1 1 d .
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'
O O 0.0106 0.0060 '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
C7 N6 N5 107.6(2)
C7 N6 C8 131.8(2)
N5 N6 C8 120.6(2)
C7 N2 C1 127.4(3)
O1 N1 O2 121.7(2)
O1 N1 C6 118.6(2)
O2 N1 C6 119.7(2)
C7 N3 N4 105.0(2)
N5 N4 N3 112.2(2)
N4 N5 N6 105.7(2)
C5 C4 C3 120.7(2)
C5 C4 Cl1 119.5(2)
C3 C4 Cl1 119.8(2)
C10 C11 C12 120.9(2)
C10 C11 Cl2 119.1(2)
C12 C11 Cl2 120.0(2)
N3 C7 N6 109.5(2)
N3 C7 N2 129.7(3)
N6 C7 N2 120.8(2)
N2 C1 C6 121.6(2)
N2 C1 C2 121.6(3)
C6 C1 C2 116.8(2)
C9 C8 C13 121.0(2)
C9 C8 N6 119.8(2)
C13 C8 N6 119.2(2)
C3 C2 C1 121.2(3)
C5 C6 C1 121.7(2)
C5 C6 N1 115.9(2)
C1 C6 N1 122.4(2)
C8 C9 C10 119.2(2)
C11 C10 C9 119.8(2)
C4 C5 C6 119.3(3)
C12 C13 C8 119.2(2)
C2 C3 C4 120.2(3)
C11 C12 C13 119.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C4 1.740(2)
Cl2 C11 1.734(3)
O2 N1 1.240(2)
O1 N1 1.226(3)
N6 C7 1.353(3)
N6 N5 1.374(3)
N6 C8 1.432(3)
N2 C7 1.362(3)
N2 C1 1.391(3)
N1 C6 1.462(3)
N3 C7 1.314(3)
N3 N4 1.371(3)
N4 N5 1.288(3)
C4 C5 1.369(3)
C4 C3 1.377(3)
C11 C10 1.372(3)
C11 C12 1.374(3)
C1 C6 1.403(3)
C1 C2 1.405(3)
C8 C9 1.376(3)
C8 C13 1.384(3)
C2 C3 1.375(3)
C6 C5 1.388(3)
C9 C10 1.384(3)
C13 C12 1.378(3)
