#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:46:54 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180315 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/29/7152927.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_7152927
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_absolute_configuration unk
_chemical_formula_moiety         'C18 H15 N O2'
_chemical_formula_sum            'C18 H15 N O2'
_chemical_formula_weight         277.31
_chemical_name_systematic
;
?
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 103.134(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   27.070(4)
_cell_length_b                   5.0325(4)
_cell_length_c                   10.3600(14)
_cell_measurement_reflns_used    3875
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      25.1
_cell_measurement_theta_min      2.8
_cell_volume                     1374.4(3)
_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, 2009)'
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ scnas 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  0.0793
_diffrn_reflns_av_sigmaI/netI    0.0751
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3875
_diffrn_reflns_theta_full        25.08
_diffrn_reflns_theta_max         25.08
_diffrn_reflns_theta_min         2.81
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0065(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         1357
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0499
_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)+(0.0624P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1259
_reflns_number_gt                947
_reflns_number_total             1357
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c3ob25867j.txt
_cod_data_source_block           k1064
_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      'C 2'
_cod_database_code               7152927
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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
O1 O 0.44729(10) 0.6403(6) 0.0602(3) 0.0517(9) Uani 1 1 d .
O2 O 0.49873(10) 0.0804(6) 0.3512(3) 0.0482(8) Uani 1 1 d .
N1 N 0.51236(13) 0.2637(8) 0.1696(4) 0.0448(9) Uani 1 1 d .
H1N H 0.5084(17) 0.387(11) 0.113(4) 0.056(15) Uiso 1 1 d .
C1 C 0.42388(15) 0.6001(9) 0.1508(4) 0.0419(10) Uani 1 1 d .
C2 C 0.37490(14) 0.7481(8) 0.1434(4) 0.0371(10) Uani 1 1 d .
C3 C 0.36287(16) 0.9562(8) 0.0528(4) 0.0462(11) Uani 1 1 d .
H3A H 0.3859 1.0037 -0.0002 0.055 Uiso 1 1 calc R
C4 C 0.31797(16) 1.0936(9) 0.0396(4) 0.0470(11) Uani 1 1 d .
H4A H 0.3103 1.2347 -0.0227 0.056 Uiso 1 1 calc R
C5 C 0.28413(16) 1.0287(8) 0.1155(4) 0.0446(11) Uani 1 1 d .
H5A H 0.2532 1.1236 0.1057 0.054 Uiso 1 1 calc R
C6 C 0.29585(16) 0.8215(8) 0.2071(4) 0.0475(12) Uani 1 1 d .
H6A H 0.2728 0.7749 0.2602 0.057 Uiso 1 1 calc R
C7 C 0.34093(14) 0.6845(8) 0.2205(4) 0.0412(11) Uani 1 1 d .
H7A H 0.3488 0.5446 0.2834 0.049 Uiso 1 1 calc R
C8 C 0.44068(15) 0.4188(9) 0.2545(4) 0.0418(10) Uani 1 1 d .
H8A H 0.4232 0.4035 0.3239 0.050 Uiso 1 1 calc R
C9 C 0.48274(16) 0.2626(8) 0.2552(4) 0.0398(10) Uani 1 1 d .
C10 C 0.54061(16) -0.0711(9) 0.3218(4) 0.0465(11) Uani 1 1 d .
H10A H 0.5298 -0.2554 0.2922 0.056 Uiso 1 1 calc R
C11 C 0.58553(15) -0.0742(9) 0.4403(4) 0.0459(11) Uani 1 1 d .
H11A H 0.5748 -0.0285 0.5228 0.055 Uiso 1 1 calc R
H11B H 0.6020 -0.2511 0.4510 0.055 Uiso 1 1 calc R
C12 C 0.62092(16) 0.1333(8) 0.4081(4) 0.0415(11) Uani 1 1 d .
C13 C 0.66485(15) 0.2353(9) 0.4873(4) 0.0459(11) Uani 1 1 d .
H13A H 0.6766 0.1712 0.5752 0.055 Uiso 1 1 calc R
C14 C 0.69199(16) 0.4330(9) 0.4382(5) 0.0515(12) Uani 1 1 d .
H14A H 0.7222 0.5033 0.4928 0.062 Uiso 1 1 calc R
C15 C 0.67505(17) 0.5258(9) 0.3109(4) 0.0495(11) Uani 1 1 d .
H15A H 0.6935 0.6614 0.2785 0.059 Uiso 1 1 calc R
C16 C 0.63110(16) 0.4226(9) 0.2288(4) 0.0454(11) Uani 1 1 d .
H16A H 0.6196 0.4856 0.1406 0.054 Uiso 1 1 calc R
C17 C 0.60422(14) 0.2241(9) 0.2788(4) 0.0392(10) Uani 1 1 d .
C18 C 0.55609(15) 0.0898(8) 0.2094(4) 0.0435(11) Uani 1 1 d .
H18A H 0.5611 -0.0266 0.1352 0.052 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C9 O2 C10 109.7(3)
C9 N1 C18 112.7(4)
O1 C1 C8 122.9(4)
O1 C1 C2 117.9(4)
C8 C1 C2 119.2(4)
C7 C2 C3 118.5(4)
C7 C2 C1 123.2(4)
C3 C2 C1 118.3(3)
C4 C3 C2 120.7(4)
C5 C4 C3 120.7(4)
C4 C5 C6 119.2(4)
C7 C6 C5 120.0(4)
C6 C7 C2 120.9(4)
C9 C8 C1 119.8(4)
N1 C9 O2 110.8(4)
N1 C9 C8 128.1(4)
O2 C9 C8 121.1(4)
O2 C10 C11 110.8(3)
O2 C10 C18 103.9(3)
C11 C10 C18 108.0(3)
C12 C11 C10 104.3(3)
C13 C12 C17 119.9(4)
C13 C12 C11 129.1(4)
C17 C12 C11 111.0(4)
C12 C13 C14 120.0(4)
C15 C14 C13 120.1(4)
C14 C15 C16 120.7(4)
C15 C16 C17 118.8(4)
C12 C17 C16 120.5(4)
C12 C17 C18 111.8(4)
C16 C17 C18 127.7(4)
N1 C18 C17 115.3(3)
N1 C18 C10 100.7(3)
C17 C18 C10 103.2(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.262(5)
O2 C9 1.349(5)
O2 C10 1.454(5)
N1 C9 1.325(5)
N1 C18 1.454(6)
C1 C8 1.404(6)
C1 C2 1.508(6)
C2 C7 1.385(5)
C2 C3 1.394(6)
C3 C4 1.378(6)
C4 C5 1.375(5)
C5 C6 1.398(6)
C6 C7 1.381(5)
C8 C9 1.382(6)
C10 C11 1.519(6)
C10 C18 1.552(6)
C11 C12 1.505(6)
C12 C13 1.381(6)
C12 C17 1.389(5)
C13 C14 1.400(6)
C14 C15 1.376(6)
C15 C16 1.396(6)
C16 C17 1.402(6)
C17 C18 1.499(6)
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
N1 H1N O1 0.84(5) 2.06(5) 2.659(5) 127(4)
