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#$Date: 2017-02-04 15:55:17 +0200 (Sat, 04 Feb 2017) $
#$Revision: 191624 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/14/7041498.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_7041498
loop_
_publ_author_name
'Deville, Claire'
'McKee, Vickie'
'McKenzie, Christine J.'
_publ_section_title
;
 Copper-promoted methylene C-H oxidation to a ketone derivative by O2.
;
_journal_issue                   3
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              709
_journal_page_last               719
_journal_paper_doi               10.1039/c6dt03349k
_journal_volume                  46
_journal_year                    2017
_chemical_formula_moiety         'C12 H11 N3 O'
_chemical_formula_sum            'C12 H11 N3 O'
_chemical_formula_weight         213.24
_chemical_name_systematic        '1,2-di(pyridin-2-yl)-ethanone oxime'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-08-11 deposited with the CCDC.
2016-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1571(7)
_cell_length_b                   13.7528(13)
_cell_length_c                   8.6319(8)
_cell_measurement_reflns_used    7244
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.45
_cell_measurement_theta_min      2.79
_cell_volume                     1087.06(17)
_computing_cell_refinement       'SAINT v.7.68a (Bruker, 2010)'
_computing_data_collection       'APEX2 v.2010.1-2 (Bruker Nonius, 2010)'
_computing_data_reduction        'SAINT v.7.68a (Bruker, 2010)'
_computing_molecular_graphics    'Mercury 3.3 (Macrae et al., 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.1
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0822
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            16000
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.672
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.3421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 793 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2110
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0571
_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
'w=1/[σ²(Fo²)+(0.1116P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1620
_refine_ls_wR_factor_ref         0.1644
_reflns_Friedel_coverage         0.853
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                1954
_reflns_number_total             2110
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6dt03349k2.cif
_cod_data_source_block           cm14106
_cod_depositor_comments
'Adding full bibliography for 7041497--7041504.cif.'
_cod_original_cell_volume        1087.07(17)
_cod_database_code               7041498
_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   0.977
_shelx_estimated_absorpt_t_max   0.983
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'
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
O1 O 0.9634(2) 0.39225(18) 0.4459(3) 0.0502(6) Uani 1 1 d . .
H1O H 0.9976 0.3546 0.3784 0.075 Uiso 1 1 calc R U
N1 N 0.5289(3) 0.5165(2) 0.6213(3) 0.0513(7) Uani 1 1 d . .
C1 C 0.3831(4) 0.5208(3) 0.6215(4) 0.0559(9) Uani 1 1 d . .
H1 H 0.3380 0.5764 0.6661 0.067 Uiso 1 1 calc R U
N2 N 0.8114(3) 0.38380(18) 0.4490(4) 0.0457(6) Uani 1 1 d . .
C2 C 0.2940(4) 0.4490(3) 0.5606(4) 0.0542(8) Uani 1 1 d . .
H2 H 0.1908 0.4559 0.5613 0.065 Uiso 1 1 calc R U
C3 C 0.3594(4) 0.3671(3) 0.4986(4) 0.0537(8) Uani 1 1 d . .
H3 H 0.3015 0.3156 0.4583 0.064 Uiso 1 1 calc R U
N3 N 0.9688(3) 0.6620(2) 0.6545(4) 0.0537(7) Uani 1 1 d . .
C4 C 0.5105(4) 0.3610(3) 0.4961(4) 0.0490(7) Uani 1 1 d . .
H4 H 0.5581 0.3057 0.4538 0.059 Uiso 1 1 calc R U
C5 C 0.5909(3) 0.4382(2) 0.5574(4) 0.0439(7) Uani 1 1 d . .
C6 C 0.7533(3) 0.4399(2) 0.5499(4) 0.0441(7) Uani 1 1 d . .
C7 C 0.8375(3) 0.5091(2) 0.6518(4) 0.0456(7) Uani 1 1 d . .
H7A H 0.9226 0.4744 0.6958 0.055 Uiso 1 1 calc R U
H7B H 0.7743 0.5293 0.7391 0.055 Uiso 1 1 calc R U
C9 C 0.8634(4) 0.6176(3) 0.4129(4) 0.0542(8) Uani 1 1 d . .
H9 H 0.8075 0.5729 0.3535 0.065 Uiso 1 1 calc R U
C8 C 0.8912(3) 0.5993(2) 0.5687(4) 0.0446(7) Uani 1 1 d . .
C10 C 0.9173(5) 0.7009(3) 0.3456(4) 0.0617(10) Uani 1 1 d . .
H10 H 0.8991 0.7139 0.2392 0.074 Uiso 1 1 calc R U
C11 C 0.9974(5) 0.7649(3) 0.4327(6) 0.0640(9) Uani 1 1 d . .
H11 H 1.0357 0.8229 0.3887 0.077 Uiso 1 1 calc R U
C12 C 1.0206(5) 0.7422(3) 0.5871(5) 0.0628(10) Uani 1 1 d . .
H12 H 1.0763 0.7861 0.6482 0.075 Uiso 1 1 calc R U
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'
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
C5 N1 C1 117.4(3)
N1 C1 C2 123.8(3)
C6 N2 O1 112.2(2)
C3 C2 C1 118.2(3)
C2 C3 C4 119.1(3)
C12 N3 C8 118.6(3)
C3 C4 C5 118.4(3)
N1 C5 C4 123.0(3)
N1 C5 C6 115.5(3)
C4 C5 C6 121.5(3)
N2 C6 C5 115.8(3)
N2 C6 C7 124.4(3)
C5 C6 C7 119.7(3)
C6 C7 C8 114.0(3)
C10 C9 C8 119.5(3)
N3 C8 C9 121.0(3)
N3 C8 C7 115.9(3)
C9 C8 C7 123.1(3)
C11 C10 C9 119.7(4)
C10 C11 C12 117.7(4)
N3 C12 C11 123.5(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N2 1.397(3)
N1 C5 1.336(4)
N1 C1 1.336(4)
C1 C2 1.385(5)
N2 C6 1.279(4)
C2 C3 1.384(5)
C3 C4 1.386(5)
N3 C12 1.335(5)
N3 C8 1.340(4)
C4 C5 1.396(4)
C5 C6 1.489(4)
C6 C7 1.508(4)
C7 C8 1.515(4)
C9 C10 1.376(5)
C9 C8 1.391(5)
C10 C11 1.372(6)
C11 C12 1.385(7)
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
O1 H1O N3 0.84 1.97 2.696(4) 144.0 2_764
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
C5 N1 C1 C2 0.4(6)
N1 C1 C2 C3 1.4(6)
C1 C2 C3 C4 -1.7(5)
C2 C3 C4 C5 0.3(5)
C1 N1 C5 C4 -1.9(5)
C1 N1 C5 C6 175.9(3)
C3 C4 C5 N1 1.6(5)
C3 C4 C5 C6 -176.1(3)
O1 N2 C6 C5 177.9(2)
O1 N2 C6 C7 1.3(4)
N1 C5 C6 N2 -158.5(3)
C4 C5 C6 N2 19.3(4)
N1 C5 C6 C7 18.2(4)
C4 C5 C6 C7 -163.9(3)
N2 C6 C7 C8 75.1(4)
C5 C6 C7 C8 -101.3(3)
C12 N3 C8 C9 -0.7(5)
C12 N3 C8 C7 179.2(3)
C10 C9 C8 N3 0.6(5)
C10 C9 C8 C7 -179.4(3)
C6 C7 C8 N3 -178.9(3)
C6 C7 C8 C9 1.0(5)
C8 C9 C10 C11 -0.2(6)
C9 C10 C11 C12 0.0(7)
C8 N3 C12 C11 0.6(6)
C10 C11 C12 N3 -0.2(7)
