#------------------------------------------------------------------------------
#$Date: 2017-11-02 07:55:23 +0100 (jue 02 de nov de 2017) $
#$Revision: 202518 $
#$URL: svn://www.crystallography.net/cod/cif/7/04/14/7041497.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_7041497
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         213.23
_chemical_name_systematic        '1,2-di(pyridin-2-yl)-ethanone oxime'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_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                61.872(4)
_cell_angle_beta                 81.346(5)
_cell_angle_gamma                75.593(4)
_cell_formula_units_Z            4
_cell_length_a                   7.3692(7)
_cell_length_b                   12.7821(12)
_cell_length_c                   13.2426(13)
_cell_measurement_reflns_used    9884
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.80
_cell_measurement_theta_min      2.86
_cell_volume                     1064.66(18)
_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 (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, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.1
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_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  0.0207
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23332
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         1.845
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.7054
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Sheldrick, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0399P)²+0.3928P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0886
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3874
_reflns_number_total             4318
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6dt03349k2.cif
_cod_data_source_block           cm1340
_cod_depositor_comments
;
Adding full bibliography for 7041497--7041504.cif.

2017-10-04
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C24 H22 N6 O2'
_cod_original_formula_weight         426.47
_cod_original_formula_moiety         'C24 H22 N6 O2'
_cod_original_formula_units_Z            2
_cod_database_code               7041497
_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   0.964
_shelx_estimated_absorpt_t_max   0.976
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.79225(11) 0.84712(7) 0.38097(7) 0.02134(18) Uani 1 1 d . .
H1O H 0.8572 0.8878 0.3894 0.032 Uiso 1 1 calc R U
N1 N 0.57869(15) 0.78615(9) 0.10615(9) 0.0283(2) Uani 1 1 d . .
C4 C 0.7895(2) 0.92287(13) 0.03825(11) 0.0338(3) Uani 1 1 d . .
H4 H 0.8676 0.9611 0.0552 0.041 Uiso 1 1 calc R U
O2 O 0.42802(11) 0.72368(7) 0.61637(6) 0.02150(18) Uani 1 1 d . .
H2O H 0.4907 0.6832 0.5834 0.032 Uiso 1 1 calc R U
N2 N 0.80178(13) 0.87169(8) 0.26628(8) 0.0196(2) Uani 1 1 d . .
C3 C 0.7741(2) 0.94613(14) -0.07310(12) 0.0400(3) Uani 1 1 d . .
H3 H 0.8427 0.9996 -0.1339 0.048 Uiso 1 1 calc R U
N3 N 0.63923(13) 0.57941(8) 0.52938(8) 0.0190(2) Uani 1 1 d . .
C2 C 0.6577(2) 0.89075(12) -0.09476(11) 0.0361(3) Uani 1 1 d . .
H2 H 0.6422 0.9064 -0.1709 0.043 Uiso 1 1 calc R U
C1 C 0.5639(2) 0.81203(13) -0.00362(12) 0.0349(3) Uani 1 1 d . .
H1 H 0.4841 0.7737 -0.0192 0.042 Uiso 1 1 calc R U
N4 N 0.18131(15) 0.69075(9) 0.96883(9) 0.0275(2) Uani 1 1 d . .
C5 C 0.68926(16) 0.84256(10) 0.12588(10) 0.0211(2) Uani 1 1 d . .
N5 N 0.39473(13) 0.64599(8) 0.73111(8) 0.0191(2) Uani 1 1 d . .
C6 C 0.69451(15) 0.81831(9) 0.24698(9) 0.0181(2) Uani 1 1 d . .
N6 N -0.01251(12) 1.00606(8) 0.63406(8) 0.01660(19) Uani 1 1 d . .
C7 C 0.56884(15) 0.74147(10) 0.33782(9) 0.0191(2) Uani 1 1 d . .
H7A H 0.4691 0.7351 0.2998 0.023 Uiso 1 1 calc R U
H7B H 0.5075 0.7830 0.3847 0.023 Uiso 1 1 calc R U
C8 C 0.66845(15) 0.61510(10) 0.41647(9) 0.0177(2) Uani 1 1 d . .
C9 C 0.77982(16) 0.53757(11) 0.37446(10) 0.0233(2) Uani 1 1 d . .
H9 H 0.7971 0.5636 0.2942 0.028 Uiso 1 1 calc R U
C10 C 0.86505(17) 0.42203(11) 0.45114(11) 0.0265(3) Uani 1 1 d . .
H10 H 0.9428 0.3684 0.4240 0.032 Uiso 1 1 calc R U
C11 C 0.83577(16) 0.38562(10) 0.56751(11) 0.0250(3) Uani 1 1 d . .
H11 H 0.8933 0.3072 0.6218 0.030 Uiso 1 1 calc R U
C12 C 0.72054(16) 0.46661(10) 0.60253(10) 0.0227(2) Uani 1 1 d . .
H12 H 0.6976 0.4413 0.6824 0.027 Uiso 1 1 calc R U
C16 C 0.28145(16) 0.50275(10) 0.95732(10) 0.0231(2) Uani 1 1 d . .
H16 H 0.3302 0.4617 0.9121 0.028 Uiso 1 1 calc R U
C15 C 0.23663(17) 0.43911(11) 1.07235(10) 0.0263(3) Uani 1 1 d . .
H15 H 0.2549 0.3533 1.1077 0.032 Uiso 1 1 calc R U
C14 C 0.16463(18) 0.50211(12) 1.13560(10) 0.0281(3) Uani 1 1 d . .
H14 H 0.1340 0.4605 1.2151 0.034 Uiso 1 1 calc R U
C13 C 0.1386(2) 0.62673(12) 1.08030(11) 0.0320(3) Uani 1 1 d . .
H13 H 0.0875 0.6697 1.1237 0.038 Uiso 1 1 calc R U
C17 C 0.25355(15) 0.62882(10) 0.90889(9) 0.0188(2) Uani 1 1 d . .
C18 C 0.30158(15) 0.70383(10) 0.78612(9) 0.0176(2) Uani 1 1 d . .
C19 C 0.23744(15) 0.83963(10) 0.73400(9) 0.0177(2) Uani 1 1 d . .
H19A H 0.3308 0.8776 0.6738 0.021 Uiso 1 1 calc R U
H19B H 0.2331 0.8658 0.7940 0.021 Uiso 1 1 calc R U
C20 C 0.04696(14) 0.88514(9) 0.68206(9) 0.0156(2) Uani 1 1 d . .
C21 C -0.06041(15) 0.80977(10) 0.68242(9) 0.0184(2) Uani 1 1 d . .
H21 H -0.0146 0.7246 0.7152 0.022 Uiso 1 1 calc R U
C22 C -0.23536(16) 0.85983(11) 0.63443(10) 0.0209(2) Uani 1 1 d . .
H22 H -0.3106 0.8096 0.6339 0.025 Uiso 1 1 calc R U
C23 C -0.29824(15) 0.98449(10) 0.58733(9) 0.0205(2) Uani 1 1 d . .
H23 H -0.4186 1.0214 0.5556 0.025 Uiso 1 1 calc R U
C24 C -0.18100(15) 1.05368(10) 0.58782(9) 0.0186(2) Uani 1 1 d . .
H24 H -0.2223 1.1392 0.5536 0.022 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 117.07(11)
C3 C4 C5 119.24(13)
C6 N2 O1 112.12(9)
C2 C3 C4 118.90(13)
C8 N3 C12 118.70(10)
C3 C2 C1 118.48(12)
N1 C1 C2 123.88(13)
C17 N4 C13 117.40(11)
N1 C5 C4 122.41(11)
N1 C5 C6 116.15(10)
C4 C5 C6 121.40(11)
C18 N5 O2 111.97(9)
N2 C6 C5 116.26(10)
N2 C6 C7 123.51(10)
C5 C6 C7 120.10(10)
C24 N6 C20 118.63(9)
C6 C7 C8 114.40(9)
N3 C8 C9 121.36(10)
N3 C8 C7 116.60(9)
C9 C8 C7 122.01(10)
C10 C9 C8 119.21(11)
C11 C10 C9 119.36(11)
C12 C11 C10 118.05(11)
N3 C12 C11 123.30(11)
C15 C16 C17 118.60(11)
C16 C15 C14 119.12(11)
C13 C14 C15 118.36(11)
N4 C13 C14 123.75(12)
N4 C17 C16 122.75(10)
N4 C17 C18 115.32(10)
C16 C17 C18 121.92(10)
N5 C18 C17 116.31(10)
N5 C18 C19 124.45(10)
C17 C18 C19 119.23(9)
C18 C19 C20 113.67(9)
N6 C20 C21 121.58(10)
N6 C20 C19 114.79(9)
C21 C20 C19 123.63(10)
C20 C21 C22 119.47(10)
C23 C22 C21 118.80(10)
C24 C23 C22 118.24(10)
N6 C24 C23 123.25(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N2 1.3926(12)
N1 C5 1.3365(15)
N1 C1 1.3456(17)
C4 C3 1.3770(19)
C4 C5 1.3937(17)
O2 N5 1.3933(12)
N2 C6 1.2843(14)
C3 C2 1.374(2)
N3 C8 1.3412(14)
N3 C12 1.3432(15)
C2 C1 1.377(2)
N4 C17 1.3401(15)
N4 C13 1.3406(16)
C5 C6 1.4877(16)
N5 C18 1.2858(14)
C6 C7 1.5076(15)
N6 C24 1.3373(14)
N6 C20 1.3437(14)
C7 C8 1.5121(15)
C8 C9 1.3939(16)
C9 C10 1.3868(17)
C10 C11 1.3827(18)
C11 C12 1.3800(17)
C16 C15 1.3802(17)
C16 C17 1.3967(16)
C15 C14 1.3861(18)
C14 C13 1.3786(18)
C17 C18 1.4879(15)
C18 C19 1.5077(15)
C19 C20 1.5129(15)
C20 C21 1.3885(15)
C21 C22 1.3886(16)
C22 C23 1.3875(16)
C23 C24 1.3842(16)
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 N6 0.84 1.88 2.6949(12) 164.7 2_676
O2 H2O N3 0.84 1.85 2.6806(12) 172.6 .
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 C4 C3 C2 1.0(2)
C4 C3 C2 C1 -1.3(2)
C5 N1 C1 C2 1.1(2)
C3 C2 C1 N1 0.3(2)
C1 N1 C5 C4 -1.44(18)
C1 N1 C5 C6 176.43(11)
C3 C4 C5 N1 0.4(2)
C3 C4 C5 C6 -177.33(12)
O1 N2 C6 C5 177.80(9)
O1 N2 C6 C7 1.84(15)
N1 C5 C6 N2 179.48(10)
C4 C5 C6 N2 -2.63(17)
N1 C5 C6 C7 -4.41(15)
C4 C5 C6 C7 173.48(11)
N2 C6 C7 C8 -78.79(14)
C5 C6 C7 C8 105.40(12)
C12 N3 C8 C9 0.34(15)
C12 N3 C8 C7 178.12(9)
C6 C7 C8 N3 128.79(10)
C6 C7 C8 C9 -53.43(14)
N3 C8 C9 C10 -1.30(16)
C7 C8 C9 C10 -178.97(10)
C8 C9 C10 C11 0.87(17)
C9 C10 C11 C12 0.47(17)
C8 N3 C12 C11 1.10(16)
C10 C11 C12 N3 -1.51(17)
C17 C16 C15 C14 0.41(18)
C16 C15 C14 C13 0.73(19)
C17 N4 C13 C14 -0.1(2)
C15 C14 C13 N4 -0.9(2)
C13 N4 C17 C16 1.32(18)
C13 N4 C17 C18 -179.00(11)
C15 C16 C17 N4 -1.49(17)
C15 C16 C17 C18 178.85(10)
O2 N5 C18 C17 178.26(8)
O2 N5 C18 C19 -0.76(14)
N4 C17 C18 N5 170.59(10)
C16 C17 C18 N5 -9.73(15)
N4 C17 C18 C19 -10.35(14)
C16 C17 C18 C19 169.34(10)
N5 C18 C19 C20 88.85(13)
C17 C18 C19 C20 -90.14(12)
C24 N6 C20 C21 1.33(15)
C24 N6 C20 C19 -178.92(9)
C18 C19 C20 N6 -179.39(9)
C18 C19 C20 C21 0.36(15)
N6 C20 C21 C22 -1.46(16)
C19 C20 C21 C22 178.81(10)
C20 C21 C22 C23 -0.07(16)
C21 C22 C23 C24 1.62(16)
C20 N6 C24 C23 0.34(16)
C22 C23 C24 N6 -1.82(17)
