Evidence for stereoelectronic effects in the N—C—N group of 8,10,12-triaza-1-azoniatetracyclo[8.3.1.1^8,12^.0^2,7^]pentadecane 4-nitrophenolate 4-nitrophenol monosolvate from the protonation of aminal (2<i>R</i>,7<i>R</i>)-1,8,10,12-tetraazatetracyclo[8.3.1.1^8,12^.0^2,7^]pentadecane: X-ray and natural bond orbital analysis
Rivera, Augusto; Uribe, Juan Manuel; Ríos-Motta, Jaime; Osorio, Hector Jairo; Bolte, Michael; Acta Crystallographica Section C 71 (2015) –; doi:10.1107/S2053229615004829

data_2019895
_publ_section_title
;
 Evidence for stereoelectronic effects in the N---C---N group of
 8,10,12-triaza-1-azoniatetracyclo[8.3.1.1^8,12^.0^2,7^]pentadecane
 4-nitrophenolate 4-nitrophenol monosolvate from the protonation of aminal
 (2<i>R</i>,7<i>R</i>)-1,8,10,12-tetraazatetracyclo[8.3.1.1^8,12^.0^2,7^]pentadecane:
 X-ray and natural bond orbital analysis
;
_journal_coeditor_code           LG3159
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229615004829
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C11 H21 N4 +, C6 H4 N O3 -, C6 H5 N O3'
_chemical_formula_moiety         'C11 H21 N4 +, C6 H4 N O3 -, C6 H5 N O3'
_chemical_formula_sum            'C23 H30 N6 O6'
_chemical_formula_weight         486.53
_chemical_name_systematic
;
8,10,12-Triaza-1-azoniatetracyclo[8.3.1.1^8,12^.0^2,7^]pentadecane
4-nitrophenolate 4-nitrophenol monosolvate
;
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 92.879(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2201(6)
_cell_length_b                   22.964(2)
_cell_length_c                   16.8626(16)
_cell_measurement_reflns_used    10933
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.9
_cell_measurement_theta_min      3.4
_cell_volume                     2405.6(4)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2001)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2001)
;
_computing_data_reduction
;
X-AREA (Stoe & Cie, 2001)
;
_computing_molecular_graphics
;
XP in SHELXTL-Plus (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Stoe IPDS II two-circle'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12586
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.614
_diffrn_reflns_theta_min         3.397
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(X-AREA; Stoe & Cie, 2001)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_description       plate
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.205
_refine_ls_abs_structure_details
;
Flack <i>x</i> parameter determined using 2249 quotients
[(I+)-(I-)]/[(I+)+(I-)] (Parsons <i>et al.</i>, 2013)
;
_refine_ls_abs_structure_Flack   -0.9(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     647
_refine_ls_number_reflns         8218
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.940
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0440
_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^)+(0.0600P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0999
_refine_ls_wR_factor_ref         0.1065
_reflns_number_gt                6220
_reflns_number_total             8218
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            lg3159sup1.cif
_cod_data_source_block           II
_cod_database_code               2019895
_shelx_estimated_absorpt_t_min   0.974
_shelx_estimated_absorpt_t_max   0.989
_shelx_hkl_checksum              96613
_shelx_res_checksum              49939
_shelxl_version_number           2014/6