Switching a HO···π Interaction to a Nonconventional OH···π Hydrogen Bond: A Completed Crystallographic Puzzle.
Kazim, Muhammad; Guan, Liangyu; Chopra, Anant; Sun, Roy; Siegler, Maxime A.; Lectka, Thomas; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01121

data_4038589
_publ_section_title
;
 Switching a HO&#x00B7;&#x00B7;&#x00B7;\p Interaction to a Nonconventional
 OH&#x00B7;&#x00B7;&#x00B7;\p Hydrogen Bond: A Completed Crystallographic
 Puzzle.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01121
_journal_year                    2020
_chemical_formula_moiety         'C23 H19 N O4'
_chemical_formula_sum            'C23 H19 N O4'
_chemical_formula_weight         373.39
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 95.2369(19)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.9450(3)
_cell_length_b                   8.13292(13)
_cell_length_c                   27.6436(5)
_cell_measurement_reflns_used    7861
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      72.0130
_cell_measurement_theta_min      2.7260
_cell_volume                     3569.84(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_molecular_graphics    'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL v6.10 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            21669
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.896
_diffrn_reflns_theta_min         2.783
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.859
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       plate
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     521
_refine_ls_number_reflns         6977
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0528
_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^)+(0.0642P)^2^+1.8672P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1421
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5430
_reflns_number_total             6977
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01121_si_001.cif
_cod_data_source_block           xs2325a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4038589
_shelx_shelxl_version_number     2018/3
_oxdiff_exptl_absorpt_empirical_full_min 0.838
_oxdiff_exptl_absorpt_empirical_full_max 1.300
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelx_res_checksum              88758
_shelx_hkl_checksum              68220