#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:46:54 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180315 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/29/7152928.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_7152928
loop_
_publ_author_name
'Jones, Roderick C.'
'Herasymchuk, Khrystyna'
'Mahdi, Tayseer'
'Petrov, Anna'
'Resanović, Sanja'
'Vaughan, Douglas G.'
'Lough, Alan J.'
'Quail, J. Wilson'
'Koivisto, Bryan D.'
'Wylie, R. Stephen'
'Gossage, Robert A.'
_publ_section_title
;
 Tautomerism and metal complexation of 2-acylmethyl-2-oxazolines: a
 combined synthetic, spectroscopic, crystallographic and theoretical
 treatment.
;
_journal_issue                   21
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3484
_journal_page_last               3493
_journal_paper_doi               10.1039/c3ob25867j
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C26 H28 Cu N2 O4'
_chemical_formula_sum            'C26 H28 Cu N2 O4'
_chemical_formula_weight         496.04
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.6720(19)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.8657(4)
_cell_length_b                   13.4020(5)
_cell_length_c                   14.1823(3)
_cell_measurement_reflns_used    16014
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.8
_cell_volume                     2403.10(13)
_computing_cell_refinement       'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius B.V., 1997-2002)'
_computing_data_reduction        Denzo-SMN
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXTL V6.1'
_computing_structure_refinement  'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_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  0.0496
_diffrn_reflns_av_sigmaI/netI    0.0626
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16014
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.81
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.943
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1036
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         5459
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0420
_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)+(0.0406P)²+1.1873P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.1036
_reflns_number_gt                3872
_reflns_number_total             5459
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c3ob25867j.txt
_cod_data_source_block           k09122
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7152928
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Cu1 Cu 0.16621(2) 0.12598(2) 0.736737(19) 0.01991(10) Uani 1 1 d .
O1 O 0.32541(14) -0.07665(13) 0.92725(12) 0.0265(4) Uani 1 1 d .
O2 O 0.01888(14) 0.21299(15) 0.46787(12) 0.0318(5) Uani 1 1 d .
O3 O 0.29991(13) 0.19366(13) 0.77131(11) 0.0248(4) Uani 1 1 d .
O4 O 0.02107(13) 0.11860(12) 0.75118(11) 0.0217(4) Uani 1 1 d .
N1 N 0.21086(15) 0.01580(15) 0.82435(13) 0.0201(4) Uani 1 1 d .
N2 N 0.12898(16) 0.17941(16) 0.60698(14) 0.0225(5) Uani 1 1 d .
C1 C 0.38002(19) 0.16848(19) 0.83685(17) 0.0212(5) Uani 1 1 d .
C2 C 0.46968(19) 0.24056(19) 0.85149(18) 0.0229(6) Uani 1 1 d .
C3 C 0.4905(2) 0.2969(2) 0.7745(2) 0.0307(6) Uani 1 1 d .
H3A H 0.4480 0.2881 0.7127 0.037 Uiso 1 1 calc R
C4 C 0.5728(2) 0.3658(2) 0.7872(2) 0.0392(7) Uani 1 1 d .
H4A H 0.5868 0.4034 0.7342 0.047 Uiso 1 1 calc R
C5 C 0.6341(2) 0.3796(2) 0.8768(3) 0.0435(8) Uani 1 1 d .
H5A H 0.6903 0.4266 0.8856 0.052 Uiso 1 1 calc R
C6 C 0.6137(2) 0.3250(2) 0.9534(2) 0.0381(7) Uani 1 1 d .
H6A H 0.6552 0.3355 1.0153 0.046 Uiso 1 1 calc R
C7 C 0.5331(2) 0.2549(2) 0.94126(19) 0.0286(6) Uani 1 1 d .
H7A H 0.5211 0.2164 0.9945 0.034 Uiso 1 1 calc R
C8 C 0.38690(19) 0.08176(19) 0.88954(17) 0.0218(5) Uani 1 1 d .
H8A H 0.4492 0.0695 0.9356 0.026 Uiso 1 1 calc R
C9 C 0.30458(19) 0.01002(18) 0.87776(16) 0.0209(5) Uani 1 1 d .
C10 C 0.2390(2) -0.14403(19) 0.88894(19) 0.0287(6) Uani 1 1 d .
H10A H 0.2172 -0.1836 0.9409 0.034 Uiso 1 1 calc R
H10B H 0.2600 -0.1902 0.8413 0.034 Uiso 1 1 calc R
C11 C 0.1497(2) -0.07513(18) 0.84171(17) 0.0234(6) Uani 1 1 d .
C12 C 0.0761(2) -0.0500(2) 0.91185(19) 0.0310(6) Uani 1 1 d .
H12A H 0.0233 -0.0010 0.8824 0.046 Uiso 1 1 calc R
H12B H 0.1177 -0.0220 0.9708 0.046 Uiso 1 1 calc R
H12C H 0.0403 -0.1108 0.9272 0.046 Uiso 1 1 calc R
C13 C 0.0889(2) -0.1180(2) 0.74839(19) 0.0315(6) Uani 1 1 d .
H13A H 0.1380 -0.1323 0.7050 0.047 Uiso 1 1 calc R
H13B H 0.0359 -0.0696 0.7183 0.047 Uiso 1 1 calc R
H13C H 0.0535 -0.1797 0.7618 0.047 Uiso 1 1 calc R
C14 C -0.06111(19) 0.11818(17) 0.68307(17) 0.0200(5) Uani 1 1 d .
C15 C -0.16305(19) 0.09147(18) 0.71330(17) 0.0224(6) Uani 1 1 d .
C16 C -0.1818(2) 0.12180(19) 0.80227(19) 0.0263(6) Uani 1 1 d .
H16A H -0.1287 0.1569 0.8450 0.032 Uiso 1 1 calc R
C17 C -0.2782(2) 0.1009(2) 0.8291(2) 0.0318(7) Uani 1 1 d .
H17A H -0.2913 0.1233 0.8893 0.038 Uiso 1 1 calc R
C18 C -0.3551(2) 0.0477(2) 0.7681(2) 0.0353(7) Uani 1 1 d .
H18A H -0.4209 0.0336 0.7865 0.042 Uiso 1 1 calc R
C19 C -0.3359(2) 0.0151(2) 0.6810(2) 0.0361(7) Uani 1 1 d .
H19A H -0.3880 -0.0226 0.6396 0.043 Uiso 1 1 calc R
C20 C -0.2407(2) 0.0373(2) 0.65355(18) 0.0283(6) Uani 1 1 d .
H20A H -0.2283 0.0152 0.5930 0.034 Uiso 1 1 calc R
C21 C -0.0601(2) 0.14215(19) 0.58903(17) 0.0237(6) Uani 1 1 d .
H21A H -0.1235 0.1356 0.5430 0.028 Uiso 1 1 calc R
C22 C 0.0324(2) 0.17626(19) 0.55875(17) 0.0236(6) Uani 1 1 d .
C23 C 0.1237(2) 0.2346(2) 0.44905(19) 0.0362(7) Uani 1 1 d .
H23A H 0.1253 0.3012 0.4192 0.043 Uiso 1 1 calc R
H23B H 0.1451 0.1839 0.4056 0.043 Uiso 1 1 calc R
C24 C 0.1974(2) 0.2317(2) 0.54771(17) 0.0264(6) Uani 1 1 d .
C25 C 0.2972(2) 0.1716(2) 0.54481(19) 0.0332(7) Uani 1 1 d .
H25A H 0.3421 0.1714 0.6086 0.050 Uiso 1 1 calc R
H25B H 0.3358 0.2019 0.4986 0.050 Uiso 1 1 calc R
H25C H 0.2778 0.1030 0.5253 0.050 Uiso 1 1 calc R
C26 C 0.2228(2) 0.3363(2) 0.5883(2) 0.0330(7) Uani 1 1 d .
H26A H 0.2601 0.3313 0.6550 0.049 Uiso 1 1 calc R
H26B H 0.1569 0.3737 0.5860 0.049 Uiso 1 1 calc R
H26C H 0.2677 0.3710 0.5500 0.049 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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
O4 Cu1 O3 146.95(7)
O4 Cu1 N1 94.06(8)
O3 Cu1 N1 92.90(8)
O4 Cu1 N2 92.63(8)
O3 Cu1 N2 96.83(8)
N1 Cu1 N2 150.79(9)
C9 O1 C10 105.88(18)
C22 O2 C23 106.65(19)
C1 O3 Cu1 127.81(16)
C14 O4 Cu1 126.71(15)
C9 N1 C11 108.3(2)
C9 N1 Cu1 123.26(16)
C11 N1 Cu1 128.39(15)
C22 N2 C24 108.8(2)
C22 N2 Cu1 121.80(16)
C24 N2 Cu1 129.33(16)
O3 C1 C8 124.8(2)
O3 C1 C2 115.0(2)
C8 C1 C2 120.1(2)
C7 C2 C3 118.5(2)
C7 C2 C1 121.6(2)
C3 C2 C1 119.9(2)
C4 C3 C2 120.6(3)
C5 C4 C3 120.0(3)
C6 C5 C4 119.8(3)
C5 C6 C7 120.7(3)
C6 C7 C2 120.4(3)
C1 C8 C9 122.5(2)
N1 C9 O1 115.1(2)
N1 C9 C8 128.3(2)
O1 C9 C8 116.6(2)
O1 C10 C11 104.40(19)
N1 C11 C13 111.49(19)
N1 C11 C10 100.86(19)
C13 C11 C10 112.2(2)
N1 C11 C12 109.6(2)
C13 C11 C12 111.6(2)
C10 C11 C12 110.7(2)
O4 C14 C21 124.8(2)
O4 C14 C15 115.2(2)
C21 C14 C15 120.0(2)
C16 C15 C20 118.7(2)
C16 C15 C14 120.0(2)
C20 C15 C14 121.3(2)
C15 C16 C17 120.2(3)
C18 C17 C16 120.2(3)
C19 C18 C17 119.9(3)
C18 C19 C20 119.9(3)
C19 C20 C15 121.0(2)
C14 C21 C22 122.0(2)
N2 C22 O2 115.3(2)
N2 C22 C21 128.7(2)
O2 C22 C21 116.0(2)
O2 C23 C24 105.4(2)
N2 C24 C25 110.7(2)
N2 C24 C26 108.9(2)
C25 C24 C26 111.9(2)
N2 C24 C23 101.2(2)
C25 C24 C23 111.7(2)
C26 C24 C23 111.9(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cu1 O4 1.9184(16)
Cu1 O3 1.9261(17)
Cu1 N1 1.947(2)
Cu1 N2 1.9499(19)
O1 C9 1.358(3)
O1 C10 1.457(3)
O2 C22 1.360(3)
O2 C23 1.451(3)
O3 C1 1.298(3)
O4 C14 1.293(3)
N1 C9 1.302(3)
N1 C11 1.496(3)
N2 C22 1.304(3)
N2 C24 1.499(3)
C1 C8 1.376(4)
C1 C2 1.489(3)
C2 C7 1.392(3)
C2 C3 1.394(4)
C3 C4 1.392(4)
C4 C5 1.378(5)
C5 C6 1.375(4)
C6 C7 1.386(4)
C8 C9 1.417(3)
C10 C11 1.529(4)
C11 C13 1.520(3)
C11 C12 1.532(3)
C14 C21 1.374(3)
C14 C15 1.497(3)
C15 C16 1.389(4)
C15 C20 1.389(3)
C16 C17 1.390(4)
C17 C18 1.385(4)
C18 C19 1.376(4)
C19 C20 1.384(4)
C21 C22 1.414(3)
C23 C24 1.539(4)
C24 C25 1.522(4)
C24 C26 1.528(4)
