3-Hydroxy-2-phenyl-2,3,3a,7a-tetrahydro-1H,5H-pyrano[3,2-b]pyrrol-5-one: crystal structure and Hirshfeld surface analysis
Zukerman-Schpector, Julio; Moro, Angélica V.; dos Santos, Marcelo R.; Correia, Carlos Roque D.; Jotani, Mukesh M.; Tiekink, Edward R. T.; Acta Crystallographica, Section E: Crystallographic Communications 73 (2017) 746–751; doi:10.1107/S2056989017005680

data_2022632
_publ_section_title
;
 3-Hydroxy-2-phenyl-2,3,3a,7a-tetrahydro-1H,5H-pyrano[3,2-b]pyrrol-5-one:
 crystal structure and Hirshfeld surface analysis
;
_journal_coden_ASTM              ACSECI
_journal_coeditor_code           HG5487
_journal_issue                   5
_journal_name_full
;
 Acta Crystallographica, Section E: Crystallographic Communications
;
_journal_page_first              746
_journal_page_last               751
_journal_paper_doi               10.1107/S2056989017005680
_journal_volume                  73
_journal_year                    2017
_chemical_absolute_configuration syn
_chemical_formula_iupac          'C13 H13 N O3'
_chemical_formula_moiety         'C13 H13 N O3'
_chemical_formula_sum            'C13 H13 N O3'
_chemical_formula_weight         231.24
_chemical_name_systematic
3-Hydroxy-2-phenyl-2,3,3a,7a-tetrahydro-1<i>H</i>,5<i>H</i>-pyrano[3,2-<i>b</i>]pyrrol-5-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 92.779(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.9638(2)
_cell_length_b                   8.4266(3)
_cell_length_c                   11.0246(4)
_cell_measurement_reflns_used    2450
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.31
_cell_measurement_theta_min      2.42
_cell_volume                     553.38(3)
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_collection
;
APEX2 (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), <i>QMol</i> (Gans & Shalloway,
2001) and
DIAMOND (Brandenburg, 2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4550
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        27.497
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         1.849
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       block
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 856 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.7(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2377
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0534P)^2^+0.0490P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0935
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_full    0.871
_reflns_Friedel_fraction_max     0.871
_reflns_number_gt                2149
_reflns_number_total             2377
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hg5487sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        553.39(3)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2022632
_publcif_datablock.id            {e66b8100-1fc5-4b0b-8e8f-abf450de8ca7}
_shelx_shelxl_version_number     2014/7
_iucr_geom_hbonds_special_details
;
Cg1 is the  centroid of the C8--C13 ring.
;
_shelx_estimated_absorpt_t_min   0.961
_shelx_estimated_absorpt_t_max   0.980
_shelx_res_checksum              933
_shelx_hkl_checksum              25274
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
_publcif_funding_html
;<span class="funder"><span class="fundref-name" 
data-id="501100003593">Conselho Nacional de Desenvolvimento Cient&#237;fico e 
Tecnol&#243;gico</span><span class="fundref-subname" data-id=""></span> (award 
No. <span class="fundref-grant">305626/2013&ndash;2</span>); </span><span 
class="funder"><span class="fundref-name" data-id="">Sunway 
University</span><span class="fundref-subname" data-id=""></span> (award No. 
<span class="fundref-grant">INT-RRO-2017-096</span>).</span>
;
_cod_database_fobs_code 2022632