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#$Date: 2016-03-26 02:11:22 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180127 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/25/7102576.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_7102576
loop_
_publ_author_name
'Czaun, Miklós'
'Speier, Gábor'
'Párkányi, László'
_publ_section_title
;
 Facile copper-mediated activation of the N-H bond and the oxidative
 cleavage of the C2-C3 bond in 1H-2-phenyl-3-hydroxy-4-oxoquinoline.
;
_journal_issue                   8
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1004
_journal_page_last               1005
_journal_paper_doi               10.1039/b315919a
_journal_year                    2004
_chemical_formula_sum            'C36 H34 Cu N4 O6'
_chemical_formula_weight         682.21
_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                101.86(1)
_cell_angle_beta                 108.49(2)
_cell_angle_gamma                107.73(2)
_cell_formula_units_Z            1
_cell_length_a                   9.340(2)
_cell_length_b                   9.626(3)
_cell_length_c                   10.522(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.39
_cell_measurement_theta_min      24.95
_cell_volume                     805.3(3)
_computing_cell_refinement       'CAD4 Express'
_computing_data_collection       'CAD4 Express'
_computing_data_reduction        'XCAD4 (Harms 1996)'
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.874
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω--2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'CU k\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6981
_diffrn_reflns_theta_full        75.16
_diffrn_reflns_theta_max         75.16
_diffrn_reflns_theta_min         4.70
_diffrn_standards_decay_%        6
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.396
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8425
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C., Philips, D.C. and Mathews, F. (1968) Acta Cryst.
A24 350-359.
;
_exptl_crystal_colour            red-brown
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             355
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.767
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2904
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0425
_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)+(0.0787P)²+0.0874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1169
_reflns_number_gt                2697
_reflns_number_total             2904
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b315919a.txt
_cod_data_source_block           cm395
_cod_database_code               7102576
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
Cu1 Cu 0.5000 0.5000 0.5000 0.03684(15) Uani 1 2 d S
O1 O 0.41564(17) 0.61456(15) 0.39069(13) 0.0452(3) Uani 1 1 d .
O2 O 0.46730(16) 0.36343(15) 0.32144(14) 0.0438(3) Uani 1 1 d .
C1 C 0.3767(2) 0.5472(2) 0.25496(18) 0.0370(3) Uani 1 1 d .
C2 C 0.3087(2) 0.6010(2) 0.14714(18) 0.0372(3) Uani 1 1 d .
N3 N 0.27614(17) 0.52385(18) 0.01099(15) 0.0404(3) Uani 1 1 d .
H3 H 0.2315 0.5613 -0.0464 0.052 Uiso 1 1 d R
C4 C 0.3019(2) 0.3931(2) -0.02867(19) 0.0405(4) Uani 1 1 d .
C5 C 0.2652(3) 0.3202(3) -0.1722(2) 0.0525(5) Uani 1 1 d .
H5 H 0.2256 0.3628 -0.2404 0.068 Uiso 1 1 calc R
C6 C 0.2879(3) 0.1868(3) -0.2112(2) 0.0607(6) Uani 1 1 d .
H6 H 0.2631 0.1386 -0.3062 0.079 Uiso 1 1 calc R
C7 C 0.3485(3) 0.1216(3) -0.1088(3) 0.0591(5) Uani 1 1 d .
H7 H 0.3616 0.0298 -0.1367 0.077 Uiso 1 1 calc R
C8 C 0.3881(2) 0.1930(2) 0.0315(2) 0.0466(4) Uani 1 1 d .
H8 H 0.4302 0.1505 0.0988 0.061 Uiso 1 1 calc R
C9 C 0.3654(2) 0.33111(19) 0.07499(18) 0.0384(4) Uani 1 1 d .
C10 C 0.40520(19) 0.41000(19) 0.21870(18) 0.0363(3) Uani 1 1 d .
C11 C 0.2678(2) 0.7378(2) 0.17086(19) 0.0391(4) Uani 1 1 d .
C12 C 0.1261(2) 0.7380(2) 0.0729(2) 0.0506(5) Uani 1 1 d .
H12 H 0.0564 0.6509 -0.0070 0.066 Uiso 1 1 calc R
C13 C 0.0891(3) 0.8672(3) 0.0943(3) 0.0602(6) Uani 1 1 d .
H13 H -0.0063 0.8660 0.0294 0.078 Uiso 1 1 calc R
C14 C 0.1937(3) 0.9985(3) 0.2120(3) 0.0584(5) Uani 1 1 d .
H14 H 0.1688 1.0854 0.2257 0.076 Uiso 1 1 calc R
C15 C 0.3344(3) 1.0001(2) 0.3085(2) 0.0558(5) Uani 1 1 d .
H15 H 0.4053 1.0888 0.3867 0.073 Uiso 1 1 calc R
C16 C 0.3710(2) 0.8702(2) 0.2895(2) 0.0465(4) Uani 1 1 d .
H16 H 0.4649 0.8712 0.3564 0.060 Uiso 1 1 calc R
N1S N 0.0992(2) 0.7101(2) -0.40288(19) 0.0556(4) Uani 1 1 d .
O1S O 0.1411(3) 0.6053(3) -0.2307(2) 0.0943(7) Uani 1 1 d .
C1S C -0.0502(4) 0.7175(5) -0.4018(3) 0.0959(11) Uani 1 1 d .
H1AS H -0.0860 0.6588 -0.3459 0.134 Uiso 1 1 calc R
H1BS H -0.1329 0.6752 -0.4974 0.134 Uiso 1 1 calc R
H1CS H -0.0324 0.8233 -0.3613 0.134 Uiso 1 1 calc R
C2S C 0.1574(3) 0.7649(4) -0.5041(3) 0.0788(8) Uani 1 1 d R
H2AS H 0.2555 0.7482 -0.4971 0.110 Uiso 1 1 calc R
H2BS H 0.1812 0.8734 -0.4830 0.110 Uiso 1 1 calc R
H2CS H 0.0739 0.7091 -0.5989 0.110 Uiso 1 1 calc R
C3S C 0.1832(3) 0.6558(3) -0.3167(3) 0.0683(6) Uani 1 1 d .
H3S H 0.2924 0.6541 -0.3216 0.089 Uiso 1 1 d 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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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
O1 Cu1 O1 180.00(5) . 2_666
O1 Cu1 O2 85.74(6) . .
O1 Cu1 O2 94.26(6) 2_666 .
O1 Cu1 O2 94.26(6) . 2_666
O1 Cu1 O2 85.74(6) 2_666 2_666
O2 Cu1 O2 180.0 . 2_666
C1 O1 Cu1 110.04(10) . .
C10 O2 Cu1 110.17(11) . .
O1 C1 C2 124.06(16) . .
O1 C1 C10 116.85(15) . .
C2 C1 C10 119.09(16) . .
N3 C2 C1 119.04(16) . .
N3 C2 C11 116.95(14) . .
C1 C2 C11 124.01(16) . .
C2 N3 C4 123.98(15) . .
N3 C4 C9 119.37(16) . .
N3 C4 C5 120.49(17) . .
C9 C4 C5 120.14(18) . .
C6 C5 C4 119.9(2) . .
C5 C6 C7 120.55(19) . .
C8 C7 C6 120.2(2) . .
C7 C8 C9 120.51(19) . .
C4 C9 C10 118.55(16) . .
C4 C9 C8 118.66(17) . .
C10 C9 C8 122.79(16) . .
O2 C10 C9 122.90(15) . .
O2 C10 C1 117.19(16) . .
C9 C10 C1 119.91(15) . .
C16 C11 C12 118.83(18) . .
C16 C11 C2 120.82(16) . .
C12 C11 C2 120.34(17) . .
C13 C12 C11 120.3(2) . .
C12 C13 C14 120.27(19) . .
C15 C14 C13 119.9(2) . .
C14 C15 C16 120.2(2) . .
C15 C16 C11 120.43(19) . .
C3S N1S C1S 121.6(2) . .
C3S N1S C2S 120.2(2) . .
C1S N1S C2S 118.2(2) . .
O1S C3S N1S 124.1(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.9067(13) .
Cu1 O1 1.9067(13) 2_666
Cu1 O2 1.9307(13) .
Cu1 O2 1.9307(13) 2_666
O1 C1 1.319(2) .
O2 C10 1.291(2) .
C1 C2 1.394(2) .
C1 C10 1.425(2) .
C2 N3 1.358(2) .
C2 C11 1.475(2) .
N3 C4 1.359(2) .
C4 C9 1.404(3) .
C4 C5 1.407(3) .
C5 C6 1.366(3) .
C6 C7 1.408(4) .
C7 C8 1.368(3) .
C8 C9 1.416(3) .
C9 C10 1.414(2) .
C11 C16 1.395(3) .
C11 C12 1.396(3) .
C12 C13 1.383(3) .
C13 C14 1.387(4) .
C14 C15 1.375(3) .
C15 C16 1.386(3) .
N1S C3S 1.305(3) .
N1S C1S 1.422(3) .
N1S C2S 1.461(3) .
O1S C3S 1.225(4) .
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
N3 H3 O1S 0.83 2.04 2.839(2) 160.7
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
O1 Cu1 O1 C1 -6(21) 2_666
O2 Cu1 O1 C1 0.82(11) .
O2 Cu1 O1 C1 -179.18(11) 2_666
O1 Cu1 O2 C10 -0.98(11) .
O1 Cu1 O2 C10 179.02(11) 2_666
O2 Cu1 O2 C10 59(14) 2_666
Cu1 O1 C1 C2 178.74(13) .
Cu1 O1 C1 C10 -0.55(19) .
O1 C1 C2 N3 178.81(15) .
C10 C1 C2 N3 -1.9(2) .
O1 C1 C2 C11 -1.7(3) .
C10 C1 C2 C11 177.54(15) .
C1 C2 N3 C4 1.7(2) .
C11 C2 N3 C4 -177.80(15) .
C2 N3 C4 C9 0.3(2) .
C2 N3 C4 C5 -179.83(16) .
N3 C4 C5 C6 -178.41(18) .
C9 C4 C5 C6 1.5(3) .
C4 C5 C6 C7 -0.3(3) .
C5 C6 C7 C8 -1.1(3) .
C6 C7 C8 C9 1.3(3) .
N3 C4 C9 C10 -1.9(2) .
C5 C4 C9 C10 178.21(16) .
N3 C4 C9 C8 178.62(15) .
C5 C4 C9 C8 -1.3(3) .
C7 C8 C9 C4 -0.1(3) .
C7 C8 C9 C10 -179.62(18) .
Cu1 O2 C10 C9 -178.97(12) .
Cu1 O2 C10 C1 0.93(18) .
C4 C9 C10 O2 -178.52(15) .
C8 C9 C10 O2 1.0(3) .
C4 C9 C10 C1 1.6(2) .
C8 C9 C10 C1 -178.93(15) .
O1 C1 C10 O2 -0.3(2) .
C2 C1 C10 O2 -179.60(14) .
O1 C1 C10 C9 179.63(14) .
C2 C1 C10 C9 0.3(2) .
N3 C2 C11 C16 -141.07(17) .
C1 C2 C11 C16 39.5(2) .
N3 C2 C11 C12 37.6(2) .
C1 C2 C11 C12 -141.87(18) .
C16 C11 C12 C13 -0.4(3) .
C2 C11 C12 C13 -179.07(18) .
C11 C12 C13 C14 1.0(3) .
C12 C13 C14 C15 -0.4(3) .
C13 C14 C15 C16 -0.9(3) .
C14 C15 C16 C11 1.6(3) .
C12 C11 C16 C15 -0.9(3) .
C2 C11 C16 C15 177.77(17) .
C1S N1S C3S O1S 1.2(5) .
C2S N1S C3S O1S -178.7(3) .
