#------------------------------------------------------------------------------
#$Date: 2023-01-06 11:50:53 +0200 (Fri, 06 Jan 2023) $
#$Revision: 280183 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/19/7061950.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_7061950
loop_
_publ_author_name
'Zhao, Lan'
'Xu, Jun'
'Ma, Jun'
'Yin, Guangwei'
'Li, Fangyi'
'Suo, Tongchuan'
'Wang, Chunhua'
_publ_section_title
;
 Formal [4+1] cyclization of (thio/imido)hydrazides and ethyl
 3,3,3-trifluoropropanoate: unified synthesis of 1,3,4-oxadiazoles,
 1,3,4-thiadiazoles and 1,2,4-triazoles
;
_journal_issue                   43
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              20755
_journal_page_last               20759
_journal_paper_doi               10.1039/D2NJ04147B
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C12 H12 N2 O3'
_chemical_formula_sum            'C12 H12 N2 O3'
_chemical_formula_weight         232.24
_chemical_name_systematic
'ethyl 2-(5-phenyl-1,3,4-oxadiazol-2-yl)acetate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-08-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-05-04 deposited with the CCDC.	2022-10-03 downloaded from the CCDC.
;
_cell_angle_alpha                85.953(9)
_cell_angle_beta                 80.093(9)
_cell_angle_gamma                75.863(7)
_cell_formula_units_Z            2
_cell_length_a                   5.6320(5)
_cell_length_b                   8.3085(7)
_cell_length_c                   12.2276(16)
_cell_measurement_reflns_used    1501
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.2550
_cell_measurement_theta_min      4.2980
_cell_volume                     546.33(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3127
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.819
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  53.00   1.00    1.00    --   12.53 -99.00 120.00   52
  2  ω    -54.00 -21.00   1.00    1.00    --   12.53 -57.00 120.00   33
  3  ω     12.00  37.00   1.00    1.00    --   12.53 -57.00 120.00   25
  4  ω      2.00  85.00   1.00    1.00    --   12.53  57.00  30.00   83
  5  ω    -11.00  84.00   1.00    1.00    --   12.53  57.00 -90.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1204015000
_diffrn_orient_matrix_UB_12      -0.0102377000
_diffrn_orient_matrix_UB_13      0.0224056000
_diffrn_orient_matrix_UB_21      0.0337941000
_diffrn_orient_matrix_UB_22      -0.0128182000
_diffrn_orient_matrix_UB_23      0.0537671000
_diffrn_orient_matrix_UB_31      -0.0408672000
_diffrn_orient_matrix_UB_32      0.0865341000
_diffrn_orient_matrix_UB_33      0.0088236000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0812
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.819
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4184
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.659
_diffrn_reflns_theta_min         3.384
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89951
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       block
_exptl_crystal_F_000             244
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       0.026(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2534
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0544
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0430P)²+0.0408P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1323
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1911
_reflns_number_total             2534
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj04147b2.cif
_cod_data_source_block           20210827a
_cod_depositor_comments
'Adding full bibliography for 7061950--7061952.cif.'
_cod_database_code               7061950
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C1H1N1O1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_diffrn_oxdiff_digest_frames
;
01944a6fcc01521f6fca6c0adef704e365000329153
;
_diffrn_oxdiff_digest_hkl
;
012dd4278ab5d36066476650dc1b45d67578fb
;
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.331
_oxdiff_exptl_absorpt_empirical_full_min 0.707
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3729(2) 0.67067(14) 0.36114(10) 0.0156(3) Uani 1 1 d . . . . .
O2 O 0.1815(2) 0.83940(15) 0.14661(10) 0.0221(3) Uani 1 1 d . . . . .
O3 O 0.1918(2) 0.64512(14) 0.02435(10) 0.0178(3) Uani 1 1 d . . . . .
N1 N 0.7761(3) 0.58237(18) 0.36382(12) 0.0196(4) Uani 1 1 d . . . . .
N2 N 0.7213(3) 0.52590(19) 0.26742(12) 0.0196(4) Uani 1 1 d . . . . .
C1 C 0.5676(3) 0.6663(2) 0.41535(14) 0.0148(4) Uani 1 1 d . . . . .
C2 C 0.4856(3) 0.5798(2) 0.26988(14) 0.0149(4) Uani 1 1 d . . . . .
C3 C 0.5222(3) 0.7547(2) 0.51908(14) 0.0153(4) Uani 1 1 d . . . . .
C4 C 0.2940(3) 0.8621(2) 0.55427(15) 0.0176(4) Uani 1 1 d . . . . .
H4 H 0.1649 0.8738 0.5138 0.021 Uiso 1 1 calc R . . . .
C5 C 0.2589(3) 0.9518(2) 0.64967(16) 0.0210(4) Uani 1 1 d . . . . .
H5 H 0.1064 1.0234 0.6735 0.025 Uiso 1 1 calc R . . . .
C6 C 0.4523(4) 0.9339(2) 0.70917(15) 0.0217(4) Uani 1 1 d . . . . .
H6 H 0.4301 0.9951 0.7725 0.026 Uiso 1 1 calc R . . . .
C7 C 0.6786(4) 0.8255(2) 0.67512(15) 0.0213(4) Uani 1 1 d . . . . .
H7 H 0.8067 0.8131 0.7162 0.026 Uiso 1 1 calc R . . . .
C8 C 0.7148(3) 0.7356(2) 0.58016(15) 0.0175(4) Uani 1 1 d . . . . .
H8 H 0.8668 0.6629 0.5573 0.021 Uiso 1 1 calc R . . . .
C9 C 0.3368(3) 0.5475(2) 0.18929(15) 0.0177(4) Uani 1 1 d . . . . .
H9A H 0.2012 0.5034 0.2295 0.021 Uiso 1 1 calc R . . . .
H9B H 0.4400 0.4625 0.1398 0.021 Uiso 1 1 calc R . . . .
C10 C 0.2302(3) 0.6968(2) 0.11992(14) 0.0159(4) Uani 1 1 d . . . . .
C11 C 0.0560(3) 0.7698(2) -0.04708(15) 0.0192(4) Uani 1 1 d . . . . .
H11A H 0.0982 0.7341 -0.1233 0.023 Uiso 1 1 calc R . . . .
H11B H 0.1027 0.8742 -0.0443 0.023 Uiso 1 1 calc R . . . .
C12 C -0.2188(3) 0.7941(2) -0.00924(16) 0.0212(4) Uani 1 1 d . . . . .
H12A H -0.3066 0.8730 -0.0582 0.032 Uiso 1 1 calc GR . . . .
H12B H -0.2612 0.8347 0.0649 0.032 Uiso 1 1 calc GR . . . .
H12C H -0.2638 0.6900 -0.0102 0.032 Uiso 1 1 calc GR . . . .
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
C2 O1 C1 102.21(12) . . ?
C10 O3 C11 117.11(13) . . ?
C1 N1 N2 105.96(15) . . ?
C2 N2 N1 106.38(13) . . ?
O1 C1 C3 119.12(14) . . ?
N1 C1 O1 112.71(15) . . ?
N1 C1 C3 128.15(17) . . ?
O1 C2 C9 120.13(14) . . ?
N2 C2 O1 112.74(16) . . ?
N2 C2 C9 127.08(15) . . ?
C4 C3 C1 120.91(17) . . ?
C4 C3 C8 120.07(16) . . ?
C8 C3 C1 118.96(15) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.06(18) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.55(17) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C7 120.49(17) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.24(19) . . ?
C8 C7 H7 119.9 . . ?
C3 C8 H8 120.2 . . ?
C7 C8 C3 119.57(17) . . ?
C7 C8 H8 120.2 . . ?
C2 C9 H9A 108.5 . . ?
C2 C9 H9B 108.5 . . ?
C2 C9 C10 115.07(14) . . ?
H9A C9 H9B 107.5 . . ?
C10 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
O2 C10 O3 125.11(18) . . ?
O2 C10 C9 125.84(17) . . ?
O3 C10 C9 109.03(14) . . ?
O3 C11 H11A 109.7 . . ?
O3 C11 H11B 109.7 . . ?
O3 C11 C12 109.99(15) . . ?
H11A C11 H11B 108.2 . . ?
C12 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
O1 C1 1.367(2) . ?
O1 C2 1.3634(19) . ?
O2 C10 1.204(2) . ?
O3 C10 1.342(2) . ?
O3 C11 1.462(2) . ?
N1 N2 1.407(2) . ?
N1 C1 1.292(2) . ?
N2 C2 1.289(2) . ?
C1 C3 1.464(2) . ?
C2 C9 1.476(3) . ?
C3 C4 1.392(2) . ?
C3 C8 1.392(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.384(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.385(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.383(2) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.511(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.505(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
