An unusually short intermolecular N—H···N hydrogen bond in crystals of the hemi-hydrochloride salt of 1-<i>exo</i>-acetamidopyrrolizidine
Bhardwaj, Minakshi; Ai, Qianxiang; Parkin, Sean R.; Grossman, Robert B.; Acta Crystallographica Section E 76 (2020) 77–81; doi:10.1107/S2056989019016517

data_2243226
_publ_section_title
;
 An unusually short intermolecular N---H&#x00B7;&#x00B7;&#x00B7;N hydrogen
 bond in crystals of the hemi-hydrochloride salt of
 1-<i>exo</i>-acetamidopyrrolizidine
;
_journal_coeditor_code           HB7870
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              77
_journal_page_last               81
_journal_paper_doi               10.1107/S2056989019016517
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          'C9 H17 N2 O1 +, Cl -, C9 H16 N2 O1'
_chemical_formula_moiety         'C18 H33 N4 O2 +, Cl -, C9 H16 N2 O1'
_chemical_formula_sum            'C18 H33 Cl N4 O2'
_chemical_formula_weight         372.93
_chemical_name_systematic
;(1<i>R</i>*, 8<i>S</i>)-2-acetamidooctahydropyrrolizin-4-ium
chloride--<i>N</i>-[(1<i>R</i>, 8<i>S</i>)hexahydro-1<i>H</i>-pyrrolizin-2-yl)acetamide (1/1)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 100.4450(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.2125(8)
_cell_length_b                   9.6926(4)
_cell_length_c                   10.1458(3)
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.34
_cell_volume                     1954.74(13)
_computing_cell_refinement
;
<i>APEX3</i> (Bruker, 2016)
;
_computing_data_collection
;
<i>APEX3</i> (Bruker, 2016)
;
_computing_data_reduction
;
<i>APEX3</i> (Bruker, 2016)
;
_computing_molecular_graphics
;
<i>XP</i> in SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
<i>SHELX</i> (Sheldrick, 2008), <i>CIFFIX</i> (Parkin, 2013)
and <i>PLATON</i> (Spek, 2009)
;
_computing_structure_refinement
;
<i>SHELXL2018/3</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 7.41
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture dual source'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            31903
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         2.338
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>SADABS</i>; Krause <i>et al.</i>,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.217
_refine_ls_extinction_coef       0.0050(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL-2018/3 (Sheldrick 2018)
;
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2235
_refine_ls_number_restraints     82
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0371
_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^)+(0.0375P)^2^+2.4571P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.0960
_reflns_number_gt                2096
_reflns_number_total             2235
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7870sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2243226
_cod_database_fobs_code          2243226
_shelx_estimated_absorpt_t_min   0.919
_shelx_estimated_absorpt_t_max   0.991
_shelx_hkl_checksum              17954
_shelx_res_checksum              66307