#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/45/4024544.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_4024544
loop_
_publ_author_name
'Mark J. Thompson'
'Harry Adams'
'Beining Chen'
_publ_contact_author_address
;University of Sheffield
Department of Chemistry
Brook Hill
Sheffield
S3 7HF
UK
;
_publ_contact_author_email       b.chen@sheffield.ac.uk
_publ_contact_author_name        'Beining Chen'
_publ_contact_author_phone       '+44 (0)114 222 9467'
_publ_section_title
;
Development of a Diversity-Oriented Approach to Oxazole-5-amide Libraries
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3856
_journal_page_last               3865
_journal_paper_doi               10.1021/jo900425w
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C20 H20 N2 O3'
_chemical_formula_weight         336.38
_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                 90.943(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.691(4)
_cell_length_b                   11.458(4)
_cell_length_c                   14.371(5)
_cell_measurement_reflns_used    952
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.23
_cell_measurement_theta_min      3.56
_cell_volume                     1760.2(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 100
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0215
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14586
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.35
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_correction_T_min  0.9582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0308
_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)+(0.0394P)²+0.3994P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0776
_reflns_number_gt                2623
_reflns_number_total             3097
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900425w_si_002.cif
_cod_data_source_block           thomp6m
_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 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed to
'constr' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4024544
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.96812(8) 0.83388(8) 0.18860(6) 0.0216(2) Uani 1 1 d . . .
N2 N 0.86075(9) 0.54391(8) 0.24433(7) 0.0221(2) Uani 1 1 d . . .
H2N H 0.9105 0.4881 0.2624 0.027 Uiso 1 1 d R . .
O1 O 0.97524(7) 0.65133(6) 0.13491(5) 0.02218(19) Uani 1 1 d . . .
O2 O 0.65752(7) 0.59742(7) 0.21880(6) 0.0285(2) Uani 1 1 d . . .
O3 O 0.71102(7) 0.42328(7) 0.28597(5) 0.02211(19) Uani 1 1 d . . .
C1 C 0.90941(10) 0.65045(10) 0.21694(8) 0.0209(3) Uani 1 1 d . . .
C2 C 0.90385(10) 0.76101(10) 0.25001(8) 0.0207(3) Uani 1 1 d . . .
C3 C 1.00728(10) 0.76531(10) 0.12287(8) 0.0207(2) Uani 1 1 d . . .
C4 C 1.07654(10) 0.79563(10) 0.03954(8) 0.0213(3) Uani 1 1 d . . .
C5 C 1.11535(11) 0.91060(10) 0.02659(8) 0.0241(3) Uani 1 1 d . . .
H5 H 1.0975 0.9680 0.0722 0.029 Uiso 1 1 calc R . .
C6 C 1.17969(11) 0.94153(11) -0.05242(8) 0.0286(3) Uani 1 1 d . . .
H6 H 1.2057 1.0200 -0.0610 0.034 Uiso 1 1 calc R . .
C7 C 1.20616(12) 0.85800(11) -0.11903(8) 0.0301(3) Uani 1 1 d . . .
H7 H 1.2517 0.8789 -0.1727 0.036 Uiso 1 1 calc R . .
C8 C 1.16622(12) 0.74399(11) -0.10725(8) 0.0296(3) Uani 1 1 d . . .
H8 H 1.1835 0.6872 -0.1535 0.036 Uiso 1 1 calc R . .
C9 C 1.10130(11) 0.71225(11) -0.02854(8) 0.0254(3) Uani 1 1 d . . .
H9 H 1.0737 0.6341 -0.0209 0.030 Uiso 1 1 calc R . .
C10 C 0.84011(10) 0.80876(10) 0.33174(8) 0.0215(3) Uani 1 1 d . . .
C11 C 0.79657(11) 0.73732(11) 0.40327(8) 0.0269(3) Uani 1 1 d . . .
H11 H 0.8088 0.6553 0.4001 0.032 Uiso 1 1 calc R . .
C12 C 0.73590(12) 0.78506(11) 0.47853(8) 0.0306(3) Uani 1 1 d . . .
H12 H 0.7073 0.7355 0.5267 0.037 Uiso 1 1 calc R . .
C13 C 0.71636(11) 0.90468(11) 0.48434(8) 0.0302(3) Uani 1 1 d . . .
H13 H 0.6742 0.9371 0.5359 0.036 Uiso 1 1 calc R . .
C14 C 0.75919(12) 0.97591(11) 0.41386(8) 0.0295(3) Uani 1 1 d . . .
H14 H 0.7464 1.0578 0.4172 0.035 Uiso 1 1 calc R . .
C15 C 0.82052(11) 0.92879(10) 0.33858(8) 0.0253(3) Uani 1 1 d . . .
H15 H 0.8497 0.9789 0.2909 0.030 Uiso 1 1 calc R . .
C16 C 0.73324(10) 0.52744(10) 0.24691(7) 0.0209(3) Uani 1 1 d . . .
C17 C 0.58068(11) 0.38150(11) 0.29844(9) 0.0283(3) Uani 1 1 d . . .
C18 C 0.51899(13) 0.36318(13) 0.20345(10) 0.0414(4) Uani 1 1 d . . .
H18A H 0.5077 0.4388 0.1725 0.062 Uiso 1 1 calc R . .
H18B H 0.4373 0.3259 0.2111 0.062 Uiso 1 1 calc R . .
H18C H 0.5722 0.3131 0.1655 0.062 Uiso 1 1 calc R . .
C19 C 0.60086(12) 0.26585(11) 0.34808(10) 0.0339(3) Uani 1 1 d . . .
H19A H 0.6540 0.2155 0.3104 0.051 Uiso 1 1 calc R . .
H19B H 0.5199 0.2277 0.3573 0.051 Uiso 1 1 calc R . .
H19C H 0.6416 0.2797 0.4087 0.051 Uiso 1 1 calc R . .
C20 C 0.51073(14) 0.46638(13) 0.35950(11) 0.0466(4) Uani 1 1 d . . .
H20A H 0.5592 0.4804 0.4169 0.070 Uiso 1 1 calc R . .
H20B H 0.4291 0.4334 0.3750 0.070 Uiso 1 1 calc R . .
H20C H 0.4986 0.5402 0.3262 0.070 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C2 105.29(10) . . ?
C16 N2 C1 120.29(9) . . ?
C16 N2 H2N 119.5 . . ?
C1 N2 H2N 120.1 . . ?
C3 O1 C1 104.35(8) . . ?
C16 O3 C17 120.63(9) . . ?
C2 C1 O1 108.55(9) . . ?
C2 C1 N2 134.82(11) . . ?
O1 C1 N2 116.55(9) . . ?
C1 C2 N1 108.12(10) . . ?
C1 C2 C10 130.60(11) . . ?
N1 C2 C10 121.22(10) . . ?
N1 C3 O1 113.68(10) . . ?
N1 C3 C4 128.64(10) . . ?
O1 C3 C4 117.67(10) . . ?
C5 C4 C9 119.52(11) . . ?
C5 C4 C3 119.35(10) . . ?
C9 C4 C3 121.10(11) . . ?
C6 C5 C4 120.30(11) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.00(12) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 119.98(12) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 C7 120.45(12) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C4 119.73(11) . . ?
C8 C9 H9 120.1 . . ?
C4 C9 H9 120.1 . . ?
C15 C10 C11 118.21(11) . . ?
C15 C10 C2 119.63(10) . . ?
C11 C10 C2 122.15(11) . . ?
C12 C11 C10 120.59(12) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.68(12) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 119.06(12) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C15 C14 C13 120.57(12) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C10 120.89(11) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
O2 C16 O3 127.58(11) . . ?
O2 C16 N2 124.04(11) . . ?
O3 C16 N2 108.38(9) . . ?
O3 C17 C20 109.60(10) . . ?
O3 C17 C19 102.20(9) . . ?
C20 C17 C19 110.83(11) . . ?
O3 C17 C18 109.25(10) . . ?
C20 C17 C18 113.42(12) . . ?
C19 C17 C18 110.94(11) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C3 1.3030(15) . ?
N1 C2 1.4029(15) . ?
N2 C16 1.3773(15) . ?
N2 C1 1.3865(15) . ?
N2 H2N 0.8692 . ?
O1 C3 1.3619(14) . ?
O1 C1 1.3829(14) . ?
O2 C16 1.2045(14) . ?
O3 C16 1.3417(14) . ?
O3 C17 1.4870(15) . ?
C1 C2 1.3547(17) . ?
C2 C10 1.4730(16) . ?
C3 C4 1.4603(16) . ?
C4 C5 1.3945(17) . ?
C4 C9 1.3958(17) . ?
C5 C6 1.3834(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.3861(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.3857(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.3855(18) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C15 1.3947(17) . ?
C10 C11 1.3997(17) . ?
C11 C12 1.3830(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.3891(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.3845(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.3840(18) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C17 C20 1.5155(19) . ?
C17 C19 1.5187(18) . ?
C17 C18 1.5209(19) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17273580
