Crystal structure of 2-(adamantan-1-yl)-5-(3,5-dinitrophenyl)-1,3,4-oxadiazole, C18H18N4O5
Al-Wahaibi, Lamya H.; Blacque, Olivier; Tiekink, Edward R. T.; El-Emam, Ali A.; Zeitschrift für Kristallographie - New Crystal Structures 237 (2022) 821–823; doi:10.1515/ncrs-2022-0263

data_8107226
_publ_section_title
;
 Crystal structure of
 2-(adamantan-1-yl)-5-(3,5-dinitrophenyl)-1,3,4-oxadiazole, C18H18N4O5
;
_journal_issue                   5
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              821
_journal_page_last               823
_journal_paper_doi               10.1515/ncrs-2022-0263
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C18 H18 N4 O5'
_chemical_formula_sum            'C18 H18 N4 O5'
_chemical_formula_weight         370.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 91.263(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7553(8)
_cell_length_b                   6.4876(4)
_cell_length_c                   22.3442(15)
_cell_measurement_reflns_used    3896
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      76.1630
_cell_measurement_theta_min      3.7410
_cell_volume                     1703.64(19)
_computing_cell_refinement       'CrysAlisPro [1]'
_computing_data_collection       'CrysAlisPro [1]'
_computing_data_reduction        'CrysAlisPro [1]'
_computing_molecular_graphics    'ORTEP-3 for Windows [4]'
_computing_publication_material  'SHELXT [3]'
_computing_structure_refinement  'SHELXT [3]'
_computing_structure_solution    'SHELXL [2]'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -27.00  26.00   0.50    6.00    --   51.70 -19.00  30.00  106
  2  \w     32.00 128.00   0.50   24.00    --  105.75 -79.00 -16.09  192
  3  \w     97.00 178.00   0.50   24.00    --  105.75  30.00 120.00  162
  4  \w     94.00 178.00   0.50   24.00    --  105.75  45.00 150.00  168
  5  \w     94.00 178.00   0.50   24.00    --  105.75  45.00  90.00  168
  6  \w     91.00 177.00   0.50   24.00    --  105.75  61.00  60.00  172
  7  \w     97.00 178.00   0.50   24.00    --  105.75  30.00-150.00  162
  8  \w     50.00 128.00   0.50   24.00    --  105.75 -79.00 -88.35  156
  9  \w     35.00  71.00   0.50   24.00    --  105.75 -61.00 -90.00   72
 10  \w     43.00  88.00   0.50   24.00    --  105.75 -77.00 -60.00   90
 11  \w     35.00  71.00   0.50   24.00    --  105.75 -61.00   0.00   72
 12  \w     35.00  71.00   0.50   24.00    --  105.75 -61.00 -60.00   72
 13  \w     35.00  71.00   0.50   24.00    --  105.75 -61.00 -30.00   72
 14  \w     35.00  71.00   0.50   24.00    --  105.75 -61.00  30.00   72
 15  \w     33.00 105.00   0.50   24.00    --  105.75 -77.00  60.00  144
 16  \w     35.00  71.00   0.50   24.00    --  105.75 -61.00 120.00   72
 17  \w     32.00 128.00   0.50   24.00    --  105.75 -79.00-143.17  192
 18  \w    -66.00  18.00   0.50    6.00    --  -54.70  57.00  30.00  168
 19  \w    -35.00  -6.00   0.50   24.00    --  -84.25  30.00 -30.00   58
 20  \w    -35.00  -6.00   0.50   24.00    --  -84.25  30.00  30.00   58
 21  \w   -127.00 -41.00   0.50    6.00    --  -54.70 -57.00 -90.00  172
 22  \w   -132.00 -46.00   0.50    6.00    --  -54.70 -38.00-180.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999, Acta A55, 543-557)'
_diffrn_orient_matrix_UB_11      0.0240267000
_diffrn_orient_matrix_UB_12      -0.2325021000
_diffrn_orient_matrix_UB_13      0.0063078000
_diffrn_orient_matrix_UB_21      0.0985799000
_diffrn_orient_matrix_UB_22      0.0196152000
_diffrn_orient_matrix_UB_23      -0.0439093000
_diffrn_orient_matrix_UB_31      0.0829161000
_diffrn_orient_matrix_UB_32      0.0442677000
_diffrn_orient_matrix_UB_33      0.0527965000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6232
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.550
_diffrn_reflns_theta_min         3.761
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.902
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro [1]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         6232
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0531
_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/[\s^2^(Fo^2^)+(0.0771P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1376
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4033
_reflns_number_total             6232
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.9337\% 
around [-0.01 -0.00 1.00] (reciprocal) or [0.00 -0.00 1.00] (direct)
;
_cod_data_source_file            suppl_j_ncrs-2022-0263_suppl.cif
_cod_data_source_block           shelx
_cod_database_code               8107226
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.898
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5597(14)
 0.4403(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C11(H11), C13(H13), C16(H16)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B), C14(H14A,H14B), C15(H15A,H15B), C17(H17A,
 H17B), C18(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6)
;
_shelx_res_checksum              97541
_shelx_hkl_checksum              50175
_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 1.532
_oxdiff_exptl_absorpt_empirical_full_min 0.723
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2