#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:59:58 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180283 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/69/7116909.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_7116909
loop_
_publ_author_name
'Cheng Xu'
'Feng-Cheng Jia'
'Qun Cai'
'Deng-Kui Li'
'Zhi-Wen Zhou'
'An-Xin Wu'
_publ_section_title
;
 Intramolecular decarboxylative coupling as the key step in
 copper-catalyzed domino reaction: facile access to
 2-(1,3,4-oxadiazol-2-yl)aniline derivatives
;
_journal_name_full               Chem.Commun.
_journal_page_first              6629
_journal_paper_doi               10.1039/C5cc01116G
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C12 H9 N3 O2'
_chemical_formula_weight         227.22
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-11-18 deposited with the CCDC.
2015-03-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   11.5359(11)
_cell_length_b                   15.7377(15)
_cell_length_c                   23.975(2)
_cell_measurement_reflns_used    323
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.21
_cell_measurement_theta_min      1.7
_cell_volume                     4352.6(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX II Smart CCD'
_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  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            31955
_diffrn_reflns_theta_full        26.21
_diffrn_reflns_theta_max         26.21
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9806
_exptl_absorpt_correction_T_min  0.9806
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         4367
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0485
_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)+(0.0763P)²+1.1946P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1369
_refine_ls_wR_factor_ref         0.1583
_reflns_number_gt                3031
_reflns_number_total             4367
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc01116g2.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7116909
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.61385(18) -0.00716(13) 0.71340(9) 0.0514(5) Uani 1 1 d . . .
C2 C 0.69735(19) -0.05244(14) 0.74377(10) 0.0589(6) Uani 1 1 d . . .
H2 H 0.7589 -0.0777 0.7249 0.071 Uiso 1 1 calc R . .
C3 C 0.6903(2) -0.06024(14) 0.80030(10) 0.0608(6) Uani 1 1 d . . .
H3 H 0.7476 -0.0899 0.8194 0.073 Uiso 1 1 calc R . .
C4 C 0.5992(2) -0.02468(14) 0.82950(9) 0.0600(6) Uani 1 1 d . . .
H4 H 0.5946 -0.0305 0.8680 0.072 Uiso 1 1 calc R . .
C5 C 0.51563(18) 0.01935(13) 0.80096(8) 0.0506(5) Uani 1 1 d . . .
H5 H 0.4537 0.0428 0.8205 0.061 Uiso 1 1 calc R . .
C6 C 0.52151(17) 0.02969(11) 0.74314(8) 0.0439(4) Uani 1 1 d . . .
C7 C 0.43439(16) 0.08001(12) 0.71492(8) 0.0448(4) Uani 1 1 d . . .
C8 C 0.28817(18) 0.16250(12) 0.70762(8) 0.0500(5) Uani 1 1 d . . .
C9 C 0.19300(18) 0.21313(13) 0.72679(9) 0.0549(4) Uani 1 1 d U . .
C10 C 0.1570(3) 0.22786(16) 0.77849(12) 0.0797(6) Uani 1 1 d U . .
H10 H 0.1876 0.2072 0.8117 0.096 Uiso 1 1 calc R . .
C11 C 0.0464(3) 0.2980(2) 0.7186(2) 0.1192(11) Uani 1 1 d U . .
H11 H -0.0103 0.3329 0.7032 0.143 Uiso 1 1 calc R . .
C12 C 0.0582(3) 0.2842(2) 0.7706(2) 0.1135(10) Uani 1 1 d U . .
H12 H 0.0116 0.3063 0.7988 0.136 Uiso 1 1 calc R . .
C13 C 0.4388(2) -0.10262(18) 0.54065(12) 0.0768(7) Uani 1 1 d . . .
H13 H 0.4850 -0.1273 0.5680 0.092 Uiso 1 1 calc R . .
C14 C 0.4493(2) -0.11214(16) 0.48641(12) 0.0739(7) Uani 1 1 d . . .
H14 H 0.5058 -0.1453 0.4693 0.089 Uiso 1 1 calc R . .
C15 C 0.3432(2) -0.04731(16) 0.54946(10) 0.0676(6) Uani 1 1 d . . .
H15 H 0.3147 -0.0283 0.5835 0.081 Uiso 1 1 calc R . .
C16 C 0.30245(18) -0.02818(13) 0.49870(8) 0.0506(5) Uani 1 1 d . . .
C17 C 0.21022(17) 0.02490(12) 0.47907(8) 0.0460(4) Uani 1 1 d . . .
C18 C 0.06227(16) 0.10596(11) 0.48617(8) 0.0436(4) Uani 1 1 d . . .
C19 C -0.02811(17) 0.15297(11) 0.51431(8) 0.0449(4) Uani 1 1 d . . .
C20 C -0.0336(2) 0.15232(14) 0.57234(8) 0.0561(5) Uani 1 1 d . . .
H20 H 0.0212 0.1216 0.5924 0.067 Uiso 1 1 calc R . .
C21 C -0.1188(2) 0.19629(16) 0.60067(10) 0.0681(6) Uani 1 1 d . . .
H21 H -0.1218 0.1951 0.6394 0.082 Uiso 1 1 calc R . .
C22 C -0.1992(2) 0.24200(16) 0.57048(10) 0.0694(7) Uani 1 1 d . . .
H22 H -0.2573 0.2715 0.5891 0.083 Uiso 1 1 calc R . .
C23 C -0.1948(2) 0.24447(14) 0.51373(10) 0.0627(6) Uani 1 1 d . . .
H23 H -0.2498 0.2762 0.4945 0.075 Uiso 1 1 calc R . .
C24 C -0.10964(17) 0.20061(12) 0.48344(9) 0.0497(5) Uani 1 1 d . . .
H24 H -0.151(3) 0.240(2) 0.4068(12) 0.101(10) Uiso 1 1 d . . .
H25 H -0.048(3) 0.1794(18) 0.4054(11) 0.088(9) Uiso 1 1 d . . .
H26 H 0.571(3) 0.038(2) 0.6382(13) 0.114(11) Uiso 1 1 d . . .
H27 H 0.687(3) -0.0175(18) 0.6396(11) 0.090(9) Uiso 1 1 d . . .
N1 N 0.42113(16) 0.09603(12) 0.66217(7) 0.0590(5) Uani 1 1 d . . .
N2 N 0.32480(17) 0.15051(12) 0.65742(7) 0.0614(5) Uani 1 1 d . . .
N3 N 0.18374(15) 0.04706(11) 0.42889(7) 0.0539(4) Uani 1 1 d . . .
N4 N 0.08649(15) 0.09995(11) 0.43376(7) 0.0520(4) Uani 1 1 d . . .
N5 N -0.1068(2) 0.20444(14) 0.42681(8) 0.0663(5) Uani 1 1 d . . .
N6 N 0.6220(2) -0.00150(19) 0.65716(9) 0.0861(8) Uani 1 1 d . . .
O1 O 0.35251(11) 0.12057(8) 0.74637(5) 0.0464(3) Uani 1 1 d . . .
O2 O 0.12790(17) 0.25512(12) 0.68818(9) 0.0917(6) Uani 1 1 d U . .
O3 O 0.13806(11) 0.05917(8) 0.51797(5) 0.0470(3) Uani 1 1 d . . .
O4 O 0.36709(14) -0.06722(10) 0.45855(7) 0.0647(4) Uani 1 1 d . . .
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
N6 C1 C2 120.2(2) . .
N6 C1 C6 122.0(2) . .
C2 C1 C6 117.81(19) . .
C3 C2 C1 121.4(2) . .
C2 C3 C4 120.8(2) . .
C5 C4 C3 119.1(2) . .
C4 C5 C6 121.34(19) . .
C5 C6 C1 119.44(18) . .
C5 C6 C7 119.59(17) . .
C1 C6 C7 120.95(17) . .
N1 C7 O1 111.42(17) . .
N1 C7 C6 130.04(17) . .
O1 C7 C6 118.51(15) . .
N2 C8 O1 112.81(18) . .
N2 C8 C9 129.21(19) . .
O1 C8 C9 117.98(18) . .
C10 C9 O2 112.2(2) . .
C10 C9 C8 129.5(2) . .
O2 C9 C8 118.3(2) . .
C9 C10 C12 103.3(3) . .
C12 C11 O2 111.4(3) . .
C11 C12 C10 108.3(3) . .
C14 C13 C15 106.8(2) . .
C13 C14 O4 111.3(2) . .
C16 C15 C13 106.0(2) . .
C15 C16 O4 110.37(19) . .
C15 C16 C17 133.7(2) . .
O4 C16 C17 115.92(18) . .
N3 C17 O3 112.78(17) . .
N3 C17 C16 129.82(18) . .
O3 C17 C16 117.39(17) . .
N4 C18 O3 111.29(16) . .
N4 C18 C19 130.39(18) . .
O3 C18 C19 118.32(16) . .
C20 C19 C24 119.79(18) . .
C20 C19 C18 119.69(18) . .
C24 C19 C18 120.51(17) . .
C21 C20 C19 121.4(2) . .
C20 C21 C22 118.8(2) . .
C23 C22 C21 120.9(2) . .
C22 C23 C24 122.0(2) . .
N5 C24 C23 120.8(2) . .
N5 C24 C19 122.1(2) . .
C23 C24 C19 117.15(19) . .
C7 N1 N2 106.86(16) . .
C8 N2 N1 105.80(16) . .
C17 N3 N4 105.81(15) . .
C18 N4 N3 107.33(16) . .
C8 O1 C7 103.12(15) . .
C9 O2 C11 104.8(3) . .
C17 O3 C18 102.78(14) . .
C14 O4 C16 105.62(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N6 1.355(3) .
C1 C2 1.402(3) .
C1 C6 1.407(3) .
C2 C3 1.363(3) .
C3 C4 1.381(3) .
C4 C5 1.371(3) .
C5 C6 1.397(3) .
C6 C7 1.447(3) .
C7 N1 1.298(2) .
C7 O1 1.367(2) .
C8 N2 1.290(3) .
C8 O1 1.360(2) .
C8 C9 1.432(3) .
C9 C10 1.328(3) .
C9 O2 1.363(3) .
C10 C12 1.457(5) .
C11 C12 1.273(5) .
C11 O2 1.368(4) .
C13 C14 1.315(4) .
C13 C15 1.420(4) .
C14 O4 1.358(3) .
C15 C16 1.339(3) .
C16 O4 1.364(2) .
C16 C17 1.432(3) .
C17 N3 1.289(2) .
C17 O3 1.361(2) .
C18 N4 1.291(2) .
C18 O3 1.374(2) .
C18 C19 1.445(3) .
C19 C20 1.393(3) .
C19 C24 1.412(3) .
C20 C21 1.380(3) .
C21 C22 1.379(3) .
C22 C23 1.362(3) .
C23 C24 1.403(3) .
C24 N5 1.360(3) .
N1 N2 1.408(3) .
N3 N4 1.402(2) .
