Synthesis and crystal structure of 4-(3-acetyl-5-(thiophen-2-yl)-2,3-dihydro-1,3,4-oxadiazol-2-yl)-7-(diethylamino)-2H-chromen-2-one, C21H21N3O4S
Yu, Xiang; Chen, Ya-Fang; Huang, Guo-Juan; Zhang, You-Fang; Yang, Wu-De; Zeitschrift für Kristallographie - New Crystal Structures 235 (2020) 561–562; doi:10.1515/ncrs-2019-0807

data_8105217
_publ_section_title
;
 Synthesis and crystal structure of
 4-(3-acetyl-5-(thiophen-2-yl)-2,3-dihydro-1,3,4-oxadiazol-2-yl)-7-(diethylamino)-2H-chromen-2-one,
 C21H21N3O4S
;
_journal_issue                   3
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              561
_journal_page_last               562
_journal_paper_doi               10.1515/ncrs-2019-0807
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C21 H21 N3 O4 S'
_chemical_formula_sum            'C21 H21 N3 O4 S'
_chemical_formula_weight         411.47
_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     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                101.896(7)
_cell_angle_beta                 104.770(8)
_cell_angle_gamma                93.271(8)
_cell_formula_units_Z            2
_cell_length_a                   9.4256(9)
_cell_length_b                   10.1906(9)
_cell_length_c                   11.6539(9)
_cell_measurement_reflns_used    2770
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.9670
_cell_measurement_theta_min      4.4410
_cell_volume                     1052.02(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9989
_diffrn_measured_fraction_theta_max 0.9769
_diffrn_measurement_details
;
  1 omega   21.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000  -30.0000 42

  2 omega   20.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000 -150.0000 43

  3 omega    6.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -99.0000 -180.0000 61

  4 omega   51.00  132.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -150.0000 81

  5 omega   84.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 30

  6 omega   77.00  116.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000  -30.0000 39

  7 omega   57.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 46

  8 omega   56.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 41

  9 omega   55.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 37

 10 omega   47.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 36

 11 omega   41.00   82.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   90.0000 41

 12 omega   39.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 47

 13 omega   76.00  127.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000    0.0000 51

 14 omega   94.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000   60.0000 82

 15 omega   69.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   37.0000  -90.0000 37

 16 omega   38.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 52

 17 omega   54.00   89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 35

 18 omega   92.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -180.0000 85

 19 omega   65.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 43

 20 omega   45.00   94.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -60.0000 49

 21 omega   41.00   66.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 25

 22 omega   11.00   58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000  -30.0000 47

 23 omega   12.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   19.0000 -120.0000 96

 24 omega   10.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919   77.0000   90.0000 94

 25 omega   59.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  178.0000  120.0000 25

 26 omega  -11.00   16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000 -150.0000 27

 27 omega  -28.00    9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.7919  -77.0000  -30.0000 37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1089117000
_diffrn_orient_matrix_UB_12      0.1296710000
_diffrn_orient_matrix_UB_13      0.0350791000
_diffrn_orient_matrix_UB_21      -0.0983587000
_diffrn_orient_matrix_UB_22      0.0742085000
_diffrn_orient_matrix_UB_23      0.0730249000
_diffrn_orient_matrix_UB_31      0.0862530000
_diffrn_orient_matrix_UB_32      -0.0433145000
_diffrn_orient_matrix_UB_33      0.1147266000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6696
_diffrn_reflns_theta_full        71.03
_diffrn_reflns_theta_max         71.03
_diffrn_reflns_theta_min         4.46
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.636
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3974
_refine_ls_number_restraints     81
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0729P)^2^+0.0838P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1354
_reflns_number_gt                3247
_reflns_number_total             3974
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2019-0807_suppl.cif
_cod_data_source_block           exp_6162
_cod_original_cell_volume        1052.01(16)
_cod_database_code               8105217
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97