2-Methyl-4-(4-nitrophenyl)but-3-yn-2-ol: crystal structure, Hirshfeld surface analysis and computational chemistry study
Caracelli, Ignez; Zukerman-Schpector, Julio; Schwab, Ricardo S.; da Silva, Everton M.; Jotani, Mukesh M.; Tiekink, Edward R. T.; Acta Crystallographica Section E 75 (2019) 1232–1238; doi:10.1107/S2056989019010284

data_2243028
_publ_section_title
;
 2-Methyl-4-(4-nitrophenyl)but-3-yn-2-ol: crystal structure, Hirshfeld
 surface analysis and computational chemistry study
;
_journal_coeditor_code           HB7841
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1232
_journal_page_last               1238
_journal_paper_doi               10.1107/S2056989019010284
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C11 H11 N O3'
_chemical_formula_moiety         'C11 H11 N O3'
_chemical_formula_sum            'C11 H11 N O3'
_chemical_formula_weight         205.21
_chemical_name_systematic
;
2-Methyl-4-(4-nitrophenyl)but-3-yn-2-ol
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_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                 90
_cell_angle_gamma                120
_cell_formula_units_Z            18
_cell_length_a                   26.3146(14)
_cell_length_b                   26.3146(14)
_cell_length_c                   8.1205(5)
_cell_measurement_reflns_used    2006
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.88
_cell_measurement_theta_min      2.66
_cell_volume                     4869.8(5)
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg,
2006)
;
_computing_publication_material
;
<i>MarvinSketch</i> (ChemAxon, 2010) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
<i>SHELXL2018/3</i> (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR2014 (Burla <i>et al.</i>, 2015)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0803
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10643
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.443
_diffrn_reflns_theta_min         1.548
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            colourles
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1944
_exptl_crystal_size_max          0.344
_exptl_crystal_size_mid          0.276
_exptl_crystal_size_min          0.161
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.272
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2230
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0527
_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^)+(0.0511P)^2^+3.9317P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1273
_refine_ls_wR_factor_ref         0.1489
_reflns_number_gt                1513
_reflns_number_total             2230
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7841sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        4869.8(6)
_cod_database_code               2243028
_cod_database_fobs_code          2243028
_shelx_estimated_absorpt_t_min   0.969
_shelx_estimated_absorpt_t_max   0.985
_shelx_hkl_checksum              15407
_shelx_res_checksum              73011