#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/32/1513233.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_1513233
loop_
_publ_author_name
'Haas, Diana'
'Mosrin, Marc'
'Knochel, Paul'
_publ_section_title
;
 Regioselective Functionalization of the Oxazole Scaffold Using TMP-Bases
 of Mg and Zn.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6162
_journal_page_last               6165
_journal_paper_doi               10.1021/ol403019c
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C13 H10 N2 O3'
_chemical_formula_sum            'C13 H10 N2 O3'
_chemical_formula_weight         242.23
_chemical_name_systematic
;
Ethyl 4-(5-cyanooxazol-2-yl)benzoate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 99.297(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.5247(2)
_cell_length_b                   28.9366(17)
_cell_length_c                   9.1022(6)
_cell_measurement_reflns_used    1593
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5280
_cell_measurement_theta_min      4.5330
_cell_volume                     1176.09(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_molecular_graphics
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
;
_computing_publication_material
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0571
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7943
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         4.23
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.388
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.175
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0739
_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)+(0.0249P)²+1.2678P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1380
_reflns_number_gt                1765
_reflns_number_total             2387
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ol403019c_si_002.cif
_cod_data_source_block           test1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1513233
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O3 O 0.3288(4) 0.31992(6) 0.3235(2) 0.0277(5) Uani 1 1 d .
O1 O 1.0312(4) 0.42134(6) -0.2723(2) 0.0263(5) Uani 1 1 d .
O2 O 0.1741(4) 0.27831(7) 0.1159(2) 0.0342(5) Uani 1 1 d .
N1 N 1.2230(5) 0.46166(8) -0.0691(3) 0.0257(5) Uani 1 1 d .
C8 C 0.5072(6) 0.34192(9) 0.1040(3) 0.0223(6) Uani 1 1 d .
C5 C 0.8574(6) 0.39870(9) -0.0450(3) 0.0210(6) Uani 1 1 d .
C9 C 0.5091(6) 0.33549(10) -0.0474(3) 0.0252(6) Uani 1 1 d .
H9 H 0.378(4) 0.3092(7) -0.1053(16) 0.030 Uiso 1 1 calc R
C12 C 0.1523(6) 0.28977(10) 0.4045(3) 0.0300(7) Uani 1 1 d .
H12A H 0.2398(18) 0.2584(6) 0.4135(4) 0.036 Uiso 1 1 calc R
H12B H -0.056(4) 0.28757(11) 0.3513(11) 0.036 Uiso 1 1 calc R
C7 C 0.6799(6) 0.37715(9) 0.1801(3) 0.0243(6) Uani 1 1 d .
H7 H 0.6772(6) 0.38201(17) 0.286(3) 0.029 Uiso 1 1 calc R
C4 C 1.2647(7) 0.45455(10) -0.4651(3) 0.0317(7) Uani 1 1 d .
C11 C 0.3192(6) 0.31007(10) 0.1795(3) 0.0244(6) Uani 1 1 d .
N2 N 1.2976(6) 0.45546(10) -0.5875(3) 0.0455(8) Uani 1 1 d .
C6 C 0.8551(6) 0.40521(10) 0.1056(3) 0.0243(6) Uani 1 1 d .
H6 H 0.979(4) 0.4301(7) 0.1603(16) 0.029 Uiso 1 1 calc R
C1 C 1.0429(6) 0.42842(9) -0.1226(3) 0.0228(6) Uani 1 1 d .
C3 C 1.2277(6) 0.45378(9) -0.3143(3) 0.0248(6) Uani 1 1 d .
C10 C 0.6834(6) 0.36357(9) -0.1222(3) 0.0245(6) Uani 1 1 d .
H10 H 0.6851(6) 0.35888(17) -0.229(3) 0.029 Uiso 1 1 calc R
C2 C 1.3438(6) 0.47784(10) -0.1901(3) 0.0269(6) Uani 1 1 d .
H2 H 1.488(5) 0.5024(8) -0.1867(3) 0.032 Uiso 1 1 calc R
C13 C 0.1569(8) 0.31041(12) 0.5547(4) 0.0472(9) Uani 1 1 d .
H13A H 0.036(5) 0.2912(6) 0.6119(15) 0.071 Uiso 1 1 calc R
H13B H 0.073(5) 0.3419(7) 0.5441(4) 0.071 Uiso 1 1 calc R
H13C H 0.365(4) 0.3117(7) 0.6074(14) 0.071 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
C11 O3 C12 115.7(2)
C1 O1 C3 104.4(2)
C1 N1 C2 104.8(2)
C9 C8 C7 119.7(3)
C9 C8 C11 117.9(2)
C7 C8 C11 122.4(3)
C6 C5 C10 120.0(3)
C6 C5 C1 119.7(2)
C10 C5 C1 120.3(2)
C10 C9 C8 120.2(3)
C10 C9 H9 119.9
C8 C9 H9 119.9
O3 C12 C13 107.2(2)
O3 C12 H12A 110.3
C13 C12 H12A 110.3
O3 C12 H12B 110.3
C13 C12 H12B 110.3
H12A C12 H12B 108.5
C6 C7 C8 120.2(3)
C6 C7 H7 119.9
C8 C7 H7 119.9
N2 C4 C3 179.3(4)
O2 C11 O3 123.8(3)
O2 C11 C8 123.3(3)
O3 C11 C8 112.9(2)
C5 C6 C7 120.1(3)
C5 C6 H6 120.0
C7 C6 H6 120.0
N1 C1 O1 113.8(2)
N1 C1 C5 128.8(2)
O1 C1 C5 117.4(2)
C2 C3 O1 107.2(2)
C2 C3 C4 135.3(3)
O1 C3 C4 117.4(2)
C9 C10 C5 119.8(3)
C9 C10 H10 120.1
C5 C10 H10 120.1
C3 C2 N1 109.8(3)
C3 C2 H2 125.1
N1 C2 H2 125.1
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C11 1.335(3)
O3 C12 1.461(3)
O1 C1 1.370(3)
O1 C3 1.388(3)
O2 C11 1.220(3)
N1 C1 1.303(3)
N1 C2 1.388(4)
C8 C9 1.392(4)
C8 C7 1.398(4)
C8 C11 1.495(4)
C5 C6 1.385(4)
C5 C10 1.403(4)
C5 C1 1.461(4)
C9 C10 1.385(4)
C9 H9 1.0533
C12 C13 1.489(4)
C12 H12A 0.9893
C12 H12B 0.9893
C7 C6 1.386(4)
C7 H7 0.9785
C4 N2 1.147(4)
C4 C3 1.410(4)
C6 H6 0.9950
C3 C2 1.359(4)
C10 H10 0.9862
C2 H2 0.9610
C13 H13A 0.9855
C13 H13B 0.9855
C13 H13C 0.9855
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
C7 C8 C9 C10 0.6(4)
C11 C8 C9 C10 -178.9(2)
C11 O3 C12 C13 -171.9(2)
C9 C8 C7 C6 -0.8(4)
C11 C8 C7 C6 178.7(2)
C12 O3 C11 O2 0.2(4)
C12 O3 C11 C8 -179.4(2)
C9 C8 C11 O2 1.7(4)
C7 C8 C11 O2 -177.8(3)
C9 C8 C11 O3 -178.7(2)
C7 C8 C11 O3 1.8(3)
C10 C5 C6 C7 -0.3(4)
C1 C5 C6 C7 -180.0(2)
C8 C7 C6 C5 0.6(4)
C2 N1 C1 O1 -0.7(3)
C2 N1 C1 C5 179.4(3)
C3 O1 C1 N1 0.4(3)
C3 O1 C1 C5 -179.7(2)
C6 C5 C1 N1 1.6(4)
C10 C5 C1 N1 -178.1(3)
C6 C5 C1 O1 -178.3(2)
C10 C5 C1 O1 2.0(4)
C1 O1 C3 C2 0.1(3)
C1 O1 C3 C4 179.5(2)
C8 C9 C10 C5 -0.3(4)
C6 C5 C10 C9 0.1(4)
C1 C5 C10 C9 179.8(2)
O1 C3 C2 N1 -0.5(3)
C4 C3 C2 N1 -179.8(3)
C1 N1 C2 C3 0.7(3)
