#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/55/4105525.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_4105525
loop_
_publ_author_name
'Israel Cano'
'Eleuterio Álvarez'
'M. Carmen Nicasio'
'Pedro J. Pérez'
_publ_section_title
;
 Regioselective Formation of 2,5-Disubstituted Oxazoles Via
 Copper(I)-Catalyzed Cycloaddition of Acyl Azides and 1-Alkynes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              191
_journal_page_last               193
_journal_paper_doi               10.1021/ja109732s
_journal_volume                  133
_journal_year                    2011
_chemical_formula_moiety         'C23 H15 N O'
_chemical_formula_sum            'C23 H15 N O'
_chemical_formula_weight         321.36
_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                 95.31(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.772(9)
_cell_length_b                   6.001(4)
_cell_length_c                   19.196(9)
_cell_measurement_reflns_used    895
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      18.29
_cell_measurement_theta_min      2.77
_cell_volume                     1694.4(17)
_computing_cell_refinement       'Bruker (2006). APEX 2. Version 2.1.'
_computing_data_collection       'Bruker (2006). APEX 2. Version 2.1.'
_computing_data_reduction        'Bruker (2006). APEX 2. Version 2.1.'
_computing_molecular_graphics    'XP, SHELXTL v. 6.14 (Bruker, 2003)'
_computing_publication_material  'XCIF, SHELXTL v. 6.14 (Bruker, 2003)'
_computing_structure_refinement  'XL, SHELXTL v. 6.14 (Bruker, 2003)'
_computing_structure_solution    'Bruker (2006). APEX 2. Version 2.1.'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
;
 Bruker-Nonius X8kappa APEX II CCD area detector'
;
_diffrn_measurement_method       'phi and omega scans with narrow frames'
_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  0.0823
_diffrn_reflns_av_sigmaI/netI    0.0865
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12808
_diffrn_reflns_theta_full        26.29
_diffrn_reflns_theta_max         26.29
_diffrn_reflns_theta_min         1.38
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_correction_T_min  0.9625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS, Bruker (2006). APEX 2. Version 2.1. Bruker Analytical
 X-ray Solutions, Madison, Wisconsin, USA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       0.046(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0720
_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)+(0.1798P)²+6.4534P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1969
_refine_ls_wR_factor_ref         0.2343
_reflns_number_gt                2257
_reflns_number_total             3387
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja109732s_si_003.cif
_cod_data_source_block           ea04410a
_cod_original_cell_volume        1694.3(17)
_cod_database_code               4105525
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
O1 O 0.8433(4) 1.1418(10) 0.5838(3) 0.0390(16) Uani 1 1 d .
N1 N 0.7049(5) 1.1370(12) 0.6200(4) 0.040(2) Uani 1 1 d .
C1 C 0.7551(6) 0.9555(14) 0.6492(4) 0.036(2) Uani 1 1 d .
C2 C 0.8394(6) 0.9597(15) 0.6274(4) 0.039(2) Uani 1 1 d .
C3 C 0.9219(6) 0.8220(15) 0.6390(5) 0.041(2) Uani 1 1 d .
C4 C 0.9171(6) 0.6199(15) 0.6741(4) 0.038(2) Uani 1 1 d .
H4 H 0.8610 0.5715 0.6895 0.046 Uiso 1 1 calc R
C5 C 0.9948(6) 0.4889(16) 0.6867(5) 0.048(3) Uani 1 1 d .
H5 H 0.9912 0.3483 0.7091 0.058 Uiso 1 1 calc R
C6 C 1.0758(7) 0.5628(18) 0.6669(6) 0.057(3) Uani 1 1 d .
H6 H 1.1289 0.4751 0.6768 0.068 Uiso 1 1 calc R
C7 C 1.0814(6) 0.7646(18) 0.6323(6) 0.054(3) Uani 1 1 d .
H7 H 1.1381 0.8144 0.6185 0.064 Uiso 1 1 calc R
C8 C 1.0042(6) 0.8930(16) 0.6179(5) 0.047(3) Uani 1 1 d .
H8 H 1.0077 1.0301 0.5936 0.056 Uiso 1 1 calc R
C9 C 0.7148(6) 0.8057(15) 0.6960(5) 0.041(2) Uani 1 1 d .
C10 C 0.6796(6) 0.6790(15) 0.7313(5) 0.042(2) Uani 1 1 d .
C11 C 0.6369(6) 0.5288(15) 0.7781(4) 0.038(2) Uani 1 1 d .
C12 C 0.5572(6) 0.5910(15) 0.8063(4) 0.040(2) Uani 1 1 d .
H12 H 0.5306 0.7321 0.7950 0.048 Uiso 1 1 calc R
C13 C 0.5164(6) 0.4482(15) 0.8507(4) 0.038(2) Uani 1 1 d .
H13 H 0.4614 0.4904 0.8691 0.046 Uiso 1 1 calc R
C14 C 0.5563(6) 0.2411(16) 0.8686(5) 0.044(2) Uani 1 1 d .
H14 H 0.5294 0.1445 0.9000 0.052 Uiso 1 1 calc R
C15 C 0.6355(6) 0.1787(15) 0.8399(4) 0.042(2) Uani 1 1 d .
H15 H 0.6623 0.0380 0.8513 0.051 Uiso 1 1 calc R
C16 C 0.6758(6) 0.3210(14) 0.7944(5) 0.039(2) Uani 1 1 d .
H16 H 0.7296 0.2768 0.7745 0.047 Uiso 1 1 calc R
C17 C 0.7594(6) 1.2409(15) 0.5824(5) 0.037(2) Uani 1 1 d .
C18 C 0.7430(6) 1.4368(14) 0.5383(4) 0.035(2) Uani 1 1 d .
C19 C 0.8095(6) 1.5318(14) 0.5031(4) 0.037(2) Uani 1 1 d .
H19 H 0.8680 1.4649 0.5053 0.045 Uiso 1 1 calc R
C20 C 0.7926(6) 1.7246(15) 0.4643(4) 0.043(2) Uani 1 1 d .
H20 H 0.8396 1.7900 0.4405 0.051 Uiso 1 1 calc R
C21 C 0.7076(6) 1.8215(15) 0.4602(5) 0.045(3) Uani 1 1 d .
H21 H 0.6958 1.9516 0.4327 0.054 Uiso 1 1 calc R
C22 C 0.6389(7) 1.7294(15) 0.4964(5) 0.045(2) Uani 1 1 d .
H22 H 0.5805 1.7969 0.4941 0.054 Uiso 1 1 calc R
C23 C 0.6571(6) 1.5361(15) 0.5362(5) 0.043(2) Uani 1 1 d .
H23 H 0.6113 1.4728 0.5617 0.051 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
C17 O1 C2 105.4(6)
C17 N1 C1 105.3(7)
C2 C1 N1 109.3(7)
C2 C1 C9 130.7(8)
N1 C1 C9 120.0(7)
C1 C2 O1 107.1(7)
C1 C2 C3 135.8(8)
O1 C2 C3 117.1(7)
C8 C3 C4 119.7(8)
C8 C3 C2 121.4(8)
C4 C3 C2 118.9(8)
C5 C4 C3 119.8(8)
C5 C4 H4 120.1
C3 C4 H4 120.1
C6 C5 C4 119.9(9)
C6 C5 H5 120.1
C4 C5 H5 120.1
C5 C6 C7 120.7(9)
C5 C6 H6 119.6
C7 C6 H6 119.6
C8 C7 C6 119.8(9)
C8 C7 H7 120.1
C6 C7 H7 120.1
C7 C8 C3 120.1(9)
C7 C8 H8 120.0
C3 C8 H8 120.0
C10 C9 C1 176.7(10)
C9 C10 C11 177.1(10)
C12 C11 C16 119.9(8)
C12 C11 C10 120.3(8)
C16 C11 C10 119.9(8)
C13 C12 C11 120.3(8)
C13 C12 H12 119.8
C11 C12 H12 119.8
C12 C13 C14 120.1(8)
C12 C13 H13 119.9
C14 C13 H13 119.9
C15 C14 C13 119.4(8)
C15 C14 H14 120.3
C13 C14 H14 120.3
C14 C15 C16 120.5(8)
C14 C15 H15 119.7
C16 C15 H15 119.7
C15 C16 C11 119.8(8)
C15 C16 H16 120.1
C11 C16 H16 120.1
N1 C17 O1 112.9(8)
N1 C17 C18 129.5(8)
O1 C17 C18 117.5(8)
C19 C18 C23 120.0(8)
C19 C18 C17 122.3(8)
C23 C18 C17 117.5(8)
C18 C19 C20 120.7(8)
C18 C19 H19 119.6
C20 C19 H19 119.6
C21 C20 C19 120.0(8)
C21 C20 H20 120.0
C19 C20 H20 120.0
C20 C21 C22 120.3(8)
C20 C21 H21 119.8
C22 C21 H21 119.8
C21 C22 C23 119.1(9)
C21 C22 H22 120.4
C23 C22 H22 120.4
C18 C23 C22 119.8(8)
C18 C23 H23 120.1
C22 C23 H23 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C17 1.373(10)
O1 C2 1.381(10)
N1 C17 1.291(11)
N1 C1 1.405(11)
C1 C2 1.350(11)
C1 C9 1.438(13)
C2 C3 1.473(12)
C3 C8 1.383(12)
C3 C4 1.393(12)
C4 C5 1.393(12)
C4 H4 0.9500
C5 C6 1.363(13)
C5 H5 0.9500
C6 C7 1.388(14)
C6 H6 0.9500
C7 C8 1.382(13)
C7 H7 0.9500
C8 H8 0.9500
C9 C10 1.172(12)
C10 C11 1.457(13)
C11 C12 1.392(12)
C11 C16 1.396(12)
C12 C13 1.385(12)
C12 H12 0.9500
C13 C14 1.404(12)
C13 H13 0.9500
C14 C15 1.390(13)
C14 H14 0.9500
C15 C16 1.394(12)
C15 H15 0.9500
C16 H16 0.9500
C17 C18 1.456(12)
C18 C19 1.368(12)
C18 C23 1.399(12)
C19 C20 1.386(12)
C19 H19 0.9500
C20 C21 1.379(12)
C20 H20 0.9500
C21 C22 1.396(13)
C21 H21 0.9500
C22 C23 1.401(12)
C22 H22 0.9500
C23 H23 0.9500
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
C17 N1 C1 C2 0.2(10)
C17 N1 C1 C9 178.5(8)
N1 C1 C2 O1 -0.6(9)
C9 C1 C2 O1 -178.7(8)
N1 C1 C2 C3 179.6(9)
C9 C1 C2 C3 1.5(17)
C17 O1 C2 C1 0.7(9)
C17 O1 C2 C3 -179.4(7)
C1 C2 C3 C8 -168.7(10)
O1 C2 C3 C8 11.5(12)
C1 C2 C3 C4 9.0(15)
O1 C2 C3 C4 -170.8(7)
C8 C3 C4 C5 -1.2(13)
C2 C3 C4 C5 -178.9(8)
C3 C4 C5 C6 2.4(14)
C4 C5 C6 C7 -2.0(15)
C5 C6 C7 C8 0.3(16)
C6 C7 C8 C3 1.0(16)
C4 C3 C8 C7 -0.5(14)
C2 C3 C8 C7 177.2(9)
C16 C11 C12 C13 0.4(12)
C10 C11 C12 C13 179.8(8)
C11 C12 C13 C14 1.1(12)
C12 C13 C14 C15 -1.7(13)
C13 C14 C15 C16 0.8(13)
C14 C15 C16 C11 0.7(13)
C12 C11 C16 C15 -1.3(13)
C10 C11 C16 C15 179.3(8)
C1 N1 C17 O1 0.3(10)
C1 N1 C17 C18 177.6(8)
C2 O1 C17 N1 -0.6(9)
C2 O1 C17 C18 -178.3(7)
N1 C17 C18 C19 177.9(9)
O1 C17 C18 C19 -4.9(12)
N1 C17 C18 C23 2.0(13)
O1 C17 C18 C23 179.2(7)
C23 C18 C19 C20 -1.0(13)
C17 C18 C19 C20 -176.8(8)
C18 C19 C20 C21 -0.7(13)
C19 C20 C21 C22 1.5(14)
C20 C21 C22 C23 -0.7(14)
C19 C18 C23 C22 1.8(13)
C17 C18 C23 C22 177.8(8)
C21 C22 C23 C18 -1.0(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660226
