#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/60/2236074.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2236074
loop_
_publ_author_name
'Rivera, Augusto'
'Osorio, Héctor Jairo'
'Sadat-Bernal, John'
'Eigner, Václav'
'Dušek, Michal'
_publ_section_title
;
 (2S,7S)-10-Ethyl-1,8,10,12-tetraazatetracyclo[8.3.1.1^8,12^.0^2,7^]pentadecan-10-ium
 iodide
;
_journal_coeditor_code           BH2451
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3041
_journal_page_last               o3042
_journal_paper_doi               10.1107/S1600536812040159
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C13 H25 N4 +, I -'
_chemical_formula_moiety         'C13 H25 N4 +, I -'
_chemical_formula_sum            'C13 H25 I N4'
_chemical_formula_weight         364.3
_chemical_melting_point          450
_chemical_name_systematic
;
(2S,7S)-10-Ethyl-1,8,10,12-
tetraazatetracyclo[8.3.1.1^8,12^.0^2,7^]pentadecan-10-ium iodide
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2227(5)
_cell_length_b                   12.0375(6)
_cell_length_c                   12.0941(6)
_cell_measurement_reflns_used    3457
_cell_measurement_temperature    120.05(10)
_cell_measurement_theta_max      27.04
_cell_measurement_theta_min      3.1
_cell_volume                     1488.25(13)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2010)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2010)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2010)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material
'JANA2006  (Petříček et al., 2006)'
_computing_structure_refinement
'JANA2006 (Petříček et al., 2006)'
_computing_structure_solution
'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      120.05
_diffrn_detector_area_resol_mean 10.3784
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device       'four-cycle diffractometer'
_diffrn_measurement_device_type  'Agilent Xcalibur (Atlas, Gemini ultra)'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            5935
_diffrn_reflns_theta_full        27.1
_diffrn_reflns_theta_max         27.1
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    2.143
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.6253
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.47
_refine_ls_abs_structure_details 'Flack (1983), 1353 Friedel pairs'
_refine_ls_abs_structure_Flack   0.026(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.19
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_constraints    0
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0180
_refine_ls_R_factor_gt           0.0170
_refine_ls_shift/su_max          0.0181
_refine_ls_shift/su_mean         0.0035
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/(σ²(I)+0.0004I²)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0407
_refine_ls_wR_factor_ref         0.0412
_reflns_number_gt                3093
_reflns_number_total             3223
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            bh2451.cif
_cod_data_source_block           I
_cod_original_formula_sum        'C13 H25 I1 N4'
_cod_database_code               2236074
_cod_database_fobs_code          2236074
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x+1/2,-y,z+1/2
3 -x,y+1/2,-z+1/2
4 x+1/2,-y+1/2,-z
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_symmetry_multiplicity
I I1 0.995575(12) 0.462386(9) 0.966324(9) 0.01806(4) Uani d 1 4
C C1 0.4852(2) 0.29285(13) 0.73421(15) 0.0153(5) Uani d 1 4
N N2 0.36266(17) 0.33495(15) 0.78149(16) 0.0157(5) Uani d 1 4
C C3 0.2959(2) 0.26756(17) 0.86111(18) 0.0170(6) Uani d 1 4
N N4 0.20151(16) 0.17701(14) 0.81134(14) 0.0141(5) Uani d 1 4
C C5 0.2742(2) 0.08504(16) 0.74916(17) 0.0146(6) Uani d 1 4
N N6 0.35735(17) 0.12860(15) 0.66504(15) 0.0148(5) Uani d 1 4
C C7 0.4840(2) 0.16841(14) 0.70831(15) 0.0142(5) Uani d 1 4
C C8 0.6008(2) 0.13825(18) 0.63737(19) 0.0198(7) Uani d 1 4
C C9 0.7262(2) 0.16905(18) 0.6984(2) 0.0213(7) Uani d 1 4
C C10 0.7278(2) 0.28974(16) 0.73715(19) 0.0212(7) Uani d 1 4
C C11 0.6056(2) 0.31806(19) 0.8036(2) 0.0180(6) Uani d 1 4
C C12 0.2718(2) 0.37477(18) 0.69715(19) 0.0211(6) Uani d 1 4
N N13 0.19918(17) 0.28513(15) 0.64344(16) 0.0194(5) Uani d 1 4
C C14 0.2834(2) 0.20109(17) 0.58957(18) 0.0191(6) Uani d 1 4
C C15 0.1162(2) 0.23336(18) 0.72399(18) 0.0186(6) Uani d 1 4
C C16 0.1232(2) 0.13179(17) 0.90618(18) 0.0203(6) Uani d 1 4
C C17 0.0267(2) 0.04169(19) 0.87726(19) 0.0289(7) Uani d 1 4
H H1c1 0.490912 0.333228 0.66593 0.0183 Uiso d 1 4
H H1c3 0.247872 0.314369 0.91096 0.0204 Uiso d 1 4
H H2c3 0.358654 0.232404 0.908641 0.0204 Uiso d 1 4
H H1c5 0.325356 0.042413 0.80047 0.0175 Uiso d 1 4
H H2c5 0.212023 0.035003 0.716646 0.0175 Uiso d 1 4
H H1c7 0.493127 0.128663 0.776687 0.017 Uiso d 1 4
H H1c8 0.600074 0.059842 0.62289 0.0237 Uiso d 1 4
H H2c8 0.596557 0.178345 0.568841 0.0237 Uiso d 1 4
H H1c9 0.800126 0.155718 0.651276 0.0256 Uiso d 1 4
H H2c9 0.737333 0.120781 0.760916 0.0256 Uiso d 1 4
H H1c10 0.804004 0.302556 0.781695 0.0254 Uiso d 1 4
H H2c10 0.733483 0.338024 0.674158 0.0254 Uiso d 1 4
H H1c11 0.606624 0.395538 0.822422 0.0216 Uiso d 1 4
H H2c11 0.603662 0.274033 0.869799 0.0216 Uiso d 1 4
H H1c12 0.211459 0.426301 0.729818 0.0254 Uiso d 1 4
H H2c12 0.319 0.416333 0.642393 0.0254 Uiso d 1 4
H H1c14 0.23152 0.156343 0.540652 0.0229 Uiso d 1 4
H H2c14 0.342843 0.237356 0.539822 0.0229 Uiso d 1 4
H H1c15 0.062251 0.178719 0.688439 0.0224 Uiso d 1 4
H H2c15 0.062416 0.288707 0.7586 0.0224 Uiso d 1 4
H H1c16 0.078397 0.191556 0.9426 0.0243 Uiso d 1 4
H H2c16 0.181437 0.105459 0.962693 0.0243 Uiso d 1 4
H H1c17 -0.019759 0.019483 0.942586 0.0346 Uiso d 1 4
H H2c17 -0.034168 0.069235 0.823415 0.0346 Uiso d 1 4
H H3c17 0.072673 -0.021042 0.847344 0.0346 Uiso d 1 4
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
I -0.4742 1.8119 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
N 0.0061 0.0033 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 C1 C7 114.27(17)
N2 C1 C11 114.02(16)
N2 C1 H1c1 102.26
C7 C1 C11 108.35(17)
C7 C1 H1c1 108.66
C11 C1 H1c1 108.95
C1 N2 C3 118.26(16)
C1 N2 C12 112.59(17)
C12 N2 C3 110.62(17)
N2 C3 N4 115.28(17)
N2 C3 H1c3 109.47
N2 C3 H2c3 109.47
N4 C3 H1c3 109.47
N4 C3 H2c3 109.47
H1c3 C3 H2c3 102.97
C3 N4 C5 113.01(15)
C3 N4 C15 107.85(15)
C3 N4 C16 106.58(15)
C5 N4 C15 104.97(15)
C16 N4 C5 111.84(15)
C16 N4 C15 112.64(15)
N4 C5 H1c5 109.47
N4 C5 H2c5 109.47
N6 C5 N4 111.96(16)
N6 C5 H1c5 109.47
N6 C5 H2c5 109.47
H1c5 C5 H2c5 106.87
C7 N6 C5 112.91(16)
C7 N6 C14 118.54(16)
C14 N6 C5 110.77(16)
C1 C7 H1c7 108.1
N6 C7 C1 113.40(17)
N6 C7 C8 114.37(16)
N6 C7 H1c7 103.22
C8 C7 C1 110.15(17)
C8 C7 H1c7 106.98
C7 C8 C9 109.28(18)
C7 C8 H1c8 109.47
C7 C8 H2c8 109.47
C9 C8 H1c8 109.47
C9 C8 H2c8 109.47
H1c8 C8 H2c8 109.66
C8 C9 C10 112.85(18)
C8 C9 H1c9 109.47
C8 C9 H2c9 109.47
C10 C9 H1c9 109.47
C10 C9 H2c9 109.47
H1c9 C9 H2c9 105.87
C9 C10 H1c10 109.47
C9 C10 H2c10 109.47
C11 C10 C9 111.49(18)
C11 C10 H1c10 109.47
C11 C10 H2c10 109.47
H1c10 C10 H2c10 107.37
C1 C11 C10 109.11(18)
C1 C11 H1c11 109.47
C1 C11 H2c11 109.47
C10 C11 H1c11 109.47
C10 C11 H2c11 109.47
H1c11 C11 H2c11 109.83
N2 C12 N13 113.02(17)
N2 C12 H1c12 109.47
N2 C12 H2c12 109.47
N13 C12 H1c12 109.47
N13 C12 H2c12 109.47
H1c12 C12 H2c12 105.67
C12 N13 C14 113.87(17)
C12 N13 C15 108.62(17)
C14 N13 C15 110.25(17)
N6 C14 N13 115.54(18)
N6 C14 H1c14 109.47
N6 C14 H2c14 109.47
N13 C14 H1c14 109.47
N13 C14 H2c14 109.47
H1c14 C14 H2c14 102.63
N4 C15 H1c15 109.47
N4 C15 H2c15 109.47
N13 C15 N4 108.96(17)
N13 C15 H1c15 109.47
N13 C15 H2c15 109.47
H1c15 C15 H2c15 109.98
N4 C16 C17 115.63(18)
N4 C16 H1c16 109.47
N4 C16 H2c16 109.47
C17 C16 H1c16 109.47
C17 C16 H2c16 109.47
H1c16 C16 H2c16 102.52
C16 C17 H1c17 109.47
C16 C17 H2c17 109.47
C16 C17 H3c17 109.47
H1c17 C17 H2c17 109.47
H1c17 C17 H3c17 109.47
H2c17 C17 H3c17 109.47
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C7 1.530(2)
C1 C11 1.521(3)
C1 H1c1 0.96
N2 C1 1.467(3)
N2 C3 1.432(3)
N2 C12 1.460(3)
C3 H1c3 0.96
C3 H2c3 0.96
N4 C3 1.575(3)
N4 C5 1.531(3)
N4 C15 1.529(3)
N4 C16 1.501(3)
C5 H1c5 0.96
C5 H2c5 0.96
N6 C5 1.426(3)
N6 C7 1.476(3)
N6 C14 1.472(3)
C7 H1c7 0.96
C8 C7 1.514(3)
C8 C9 1.526(3)
C8 H1c8 0.96
C8 H2c8 0.96
C9 H1c9 0.96
C9 H2c9 0.96
C10 C9 1.527(3)
C10 C11 1.524(3)
C10 H1c10 0.96
C10 H2c10 0.96
C11 H1c11 0.96
C11 H2c11 0.96
C12 H1c12 0.96
C12 H2c12 0.96
N13 C12 1.462(3)
N13 C14 1.480(3)
N13 C15 1.434(3)
C14 H1c14 0.96
C14 H2c14 0.96
C15 H1c15 0.96
C15 H2c15 0.96
C16 H1c16 0.96
C16 H2c16 0.96
C17 C16 1.507(3)
C17 H1c17 0.96
C17 H2c17 0.96
C17 H3c17 0.96
