O⋯π and O–H⋯π interactions: the first disclosure of the nature of 1,3,4-oxadiazol⋯aromatic contacts
Wang, Li; Zhang, Zhenfeng; Wang, Yibo; Wu, Yanbo; Zhang, Shengyong; CrystEngComm 14 (2012) 7877–; doi:10.1039/c2ce26224j

data_7208818
_publ_section_title
;
 O&#x22EF;\p and O--H&#x22EF;\p interactions: the first disclosure of the
 nature of 1,3,4-oxadiazol&#x22EF;aromatic contacts
;
_journal_issue                   23
_journal_name_full               CrystEngComm
_journal_page_first              7877
_journal_paper_doi               10.1039/c2ce26224j
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration rm
_chemical_formula_sum            'C19 H17 N3 O5'
_chemical_formula_weight         367.36
_chemical_name_common
;
methyl (2R,3S)-2-hydroxy-3-phenyl-3-(((5-phenyl-1,3,4-
oxadiazol-2-yl)-carbonyl)amino)-propanoate
;
_chemical_name_systematic
;
methyl (2R,3S)-2-hydroxy-3-phenyl-3-{[(5-phenyl-1,3,4-oxadiazol-
2-yl)-carbonyl]amino}-propanoate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.7956(15)
_cell_length_b                   11.993(3)
_cell_length_c                   21.790(5)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.1
_cell_measurement_theta_min      3.1
_cell_volume                     1775.9(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8686
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         3.14
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9821
_exptl_absorpt_correction_T_min  0.9617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.110
_refine_diff_density_min         -0.087
_refine_diff_density_rms         0.024
_refine_ls_extinction_coef       0.054(3)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3080
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0246
_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/[\s^2^(Fo^2^)+(0.0362P)^2^+0.1015P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0615
_refine_ls_wR_factor_ref         0.0638
_reflns_number_gt                2888
_reflns_number_total             3080
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce26224j.txt
_cod_data_source_block           xb4195
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P212121
_cod_database_code               7208818
_hbond_acceptor_comment
;
In the cif file, there exists a "B alert" regarding the
O5-H5A without acceptor. The hydroxyl O5-H5A could have
formed a conventional intramolecular H-bond to the carbonyl
O4 (Fig. 5), however, the hydroxyl atom H5A points not to
the O4 atom but to the centroid of C11-C16 ring of the
neighboring translation-related molecule. It shows
that here the p-cloud of the C11*-C16* ring acts as the
acceptor of the O5-H5A, which can be verified
by the H-bond geometry H5A Cg and O5 Cg being
2.69 and 3.460(2)A, respectively, and the H-bond angle 161A.
;