#------------------------------------------------------------------------------
#$Date: 2016-03-21 05:29:08 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178480 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/01/4030139.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4030139
loop_
_publ_author_name
'Yang, Bo'
'Zheng, Li-Mei'
'Gao, Zhong-Zheng'
'Xiao, Xin'
'Zhu, Qian-Jiang'
'Xue, Sai-Feng'
'Tao, Zhu'
'Liu, Jing-Xin'
'Wei, Gang'
_publ_section_title
;
 Extended and contorted conformations of alkanediammonium ions in
 symmetrical α,α',δ,δ'-tetramethylcucurbit[6]uril cavity.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11194
_journal_page_last               11198
_journal_paper_doi               10.1021/jo502255x
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C46 H82 N28 O28'
_chemical_formula_weight         1475.40
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                118.978(3)
_cell_angle_beta                 95.084(4)
_cell_angle_gamma                104.624(4)
_cell_formula_units_Z            1
_cell_length_a                   12.2970(16)
_cell_length_b                   12.3805(9)
_cell_length_c                   12.5907(9)
_cell_measurement_reflns_used    4680
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.44
_cell_measurement_theta_min      0.00
_cell_volume                     1571.4(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker Smart Apex CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17925
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.77
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.9770
_exptl_absorpt_correction_T_min  0.9708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             778
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.837
_refine_diff_density_min         -0.617
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       0.021(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         6007
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0828
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1850P)²+1.1338P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2471
_refine_ls_wR_factor_ref         0.2764
_reflns_number_gt                4436
_reflns_number_total             6007
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502255x_si_004.cif
_cod_data_source_block           TMeQ[6]+C6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'multi scan'
changed to 'multi-scan' according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Adding full bibliography for 4030138--4030142.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4030139
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 1.3560(3) 0.8880(3) 1.1485(3) 0.0443(8) Uani 1 1 d .
H1A H 1.4392 0.9298 1.1833 0.053 Uiso 1 1 calc R
H1B H 1.3267 0.9480 1.1364 0.053 Uiso 1 1 calc R
C2 C 0.7070(3) 0.6535(4) 1.2877(3) 0.0466(8) Uani 1 1 d .
H2A H 0.6589 0.6394 1.3400 0.056 Uiso 1 1 calc R
H2B H 0.6945 0.7239 1.2799 0.056 Uiso 1 1 calc R
C3 C 0.9105(3) 0.7892(3) 1.3471(3) 0.0389(7) Uani 1 1 d .
C4 C 1.1149(3) 0.9259(3) 1.4463(3) 0.0418(7) Uani 1 1 d .
H4A H 1.0897 0.9845 1.4277 0.050 Uiso 1 1 calc R
H4B H 1.1556 0.9761 1.5343 0.050 Uiso 1 1 calc R
C5 C 1.2152(3) 0.9073(3) 1.2793(3) 0.0373(7) Uani 1 1 d .
C6 C 1.2576(3) 0.7385(3) 0.9241(3) 0.0400(7) Uani 1 1 d .
C7 C 0.8006(3) 0.6779(4) 1.5352(3) 0.0526(9) Uani 1 1 d .
H7A H 0.7220 0.6195 1.4941 0.079 Uiso 1 1 calc R
H7B H 0.8018 0.7669 1.5801 0.079 Uiso 1 1 calc R
H7C H 0.8340 0.6583 1.5929 0.079 Uiso 1 1 calc R
C8 C 0.8706(3) 0.6603(3) 1.4381(3) 0.0382(7) Uani 1 1 d .
C9 C 1.0431(3) 0.8423(3) 1.6329(3) 0.0430(7) Uani 1 1 d .
H9A H 1.1239 0.8929 1.6568 0.065 Uiso 1 1 calc R
H9B H 1.0312 0.7911 1.6714 0.065 Uiso 1 1 calc R
H9C H 0.9988 0.9003 1.6600 0.065 Uiso 1 1 calc R
C10 C 1.0040(3) 0.7517(3) 1.4914(3) 0.0351(6) Uani 1 1 d .
C11 C 1.2841(3) 0.8412(3) 1.4095(3) 0.0368(7) Uani 1 1 d .
H11A H 1.3299 0.9062 1.4958 0.044 Uiso 1 1 calc R
C12 C 1.3589(3) 0.8267(3) 1.3136(3) 0.0383(7) Uani 1 1 d .
H12A H 1.4400 0.8835 1.3552 0.046 Uiso 1 1 calc R
C13 C 1.4045(3) 0.6862(3) 0.9987(3) 0.0411(7) Uani 1 1 d .
H13A H 1.4873 0.7378 1.0253 0.049 Uiso 1 1 calc R
C14 C 0.7811(3) 0.4071(3) 1.3042(3) 0.0422(7) Uani 1 1 d .
H14A H 0.7198 0.4152 1.3479 0.051 Uiso 1 1 calc R
H14B H 0.8051 0.3370 1.3012 0.051 Uiso 1 1 calc R
C15 C 0.9896(3) 0.5287(3) 1.3819(3) 0.0355(6) Uani 1 1 d .
C16 C 1.1879(3) 0.6829(3) 1.4731(3) 0.0377(7) Uani 1 1 d .
H16A H 1.2227 0.7575 1.5580 0.045 Uiso 1 1 calc R
H16B H 1.2038 0.6083 1.4692 0.045 Uiso 1 1 calc R
C17 C 1.2844(2) 0.6255(3) 1.3001(3) 0.0356(7) Uani 1 1 d .
C18 C 1.4219(3) 0.6365(4) 1.1717(3) 0.0433(7) Uani 1 1 d .
H18A H 1.4293 0.5619 1.1750 0.052 Uiso 1 1 calc R
H18B H 1.4984 0.7027 1.2054 0.052 Uiso 1 1 calc R
C19 C 1.3467(3) 0.4667(3) 0.9459(3) 0.0413(7) Uani 1 1 d .
C20 C 0.6381(3) 0.4053(3) 1.1455(3) 0.0423(7) Uani 1 1 d .
H20A H 0.5772 0.3905 1.1870 0.051 Uiso 1 1 calc R
N1 N 0.6695(2) 0.5356(3) 1.1651(2) 0.0444(7) Uani 1 1 d .
N2 N 0.8277(2) 0.6951(3) 1.3505(3) 0.0412(6) Uani 1 1 d .
N3 N 1.0133(2) 0.8217(3) 1.4259(2) 0.0385(6) Uani 1 1 d .
N4 N 1.3035(2) 0.8647(3) 1.2376(2) 0.0399(6) Uani 1 1 d .
N5 N 1.1950(2) 0.8817(3) 1.3722(2) 0.0400(6) Uani 1 1 d .
N6 N 1.3329(2) 0.7684(3) 1.0274(2) 0.0431(6) Uani 1 1 d .
N7 N 0.7350(2) 0.3710(3) 1.1768(2) 0.0408(6) Uani 1 1 d .
N8 N 0.8785(2) 0.5283(2) 1.3746(2) 0.0384(6) Uani 1 1 d .
N9 N 1.0634(2) 0.6541(2) 1.4470(2) 0.0375(6) Uani 1 1 d .
N10 N 1.2425(2) 0.7113(3) 1.3886(2) 0.0375(6) Uani 1 1 d .
N11 N 1.3472(2) 0.6888(3) 1.2494(2) 0.0407(6) Uani 1 1 d .
N12 N 1.3801(2) 0.5953(3) 1.0420(2) 0.0416(6) Uani 1 1 d .
O1 O 0.8948(2) 0.8390(2) 1.2866(2) 0.0483(6) Uani 1 1 d .
O2 O 1.1630(2) 0.9583(2) 1.2421(2) 0.0508(6) Uani 1 1 d .
O3 O 1.1940(2) 0.7992(2) 0.9210(2) 0.0506(6) Uani 1 1 d .
O4 O 1.0176(2) 0.4302(2) 1.3388(2) 0.0434(5) Uani 1 1 d .
O5 O 1.2685(2) 0.5123(2) 1.2704(2) 0.0455(5) Uani 1 1 d .
N14 N 1.5203(5) 0.7844(6) 1.5409(5) 0.129(3) Uani 1 1 d D
O6 O 1.3360(2) 0.3725(3) 0.9559(2) 0.0520(6) Uani 1 1 d .
O7 O 1.5717(8) 0.8366(10) 1.4857(8) 0.226(4) Uani 1 1 d D
O8 O 1.5058(8) 0.6717(6) 1.4999(11) 0.288(7) Uani 1 1 d D
O9 O 1.4748(5) 0.8486(7) 1.6152(6) 0.190(4) Uani 1 1 d D
O1W O 1.3946(8) 0.3457(8) 1.2608(10) 0.093(2) Uani 0.45 1 d P
O1W' O 1.4885(14) 0.4280(12) 1.3551(15) 0.091(4) Uani 0.25 1 d PD
O1W" O 1.3421(11) 0.2688(13) 1.1241(15) 0.094(4) Uani 0.30 1 d P
O2W O 0.5476(7) 0.1487(7) 1.1573(8) 0.199(3) Uani 1 1 d .
O3W O 0.6775(4) 0.9157(4) 1.2495(4) 0.1012(12) Uani 1 1 d .
O4W O 0.8418(7) 0.9157(6) 0.8952(6) 0.205(2) Uani 1 1 d .
O5W O 1.3574(7) 1.0443(8) 0.9504(8) 0.190(3) Uani 1 1 d .
N13 N 0.9446(3) 0.7370(3) 0.8947(3) 0.0631(9) Uani 1 1 d .
H13B H 0.9128 0.7950 0.8971 0.095 Uiso 1 1 calc R
H13C H 0.9091 0.6598 0.8241 0.095 Uiso 1 1 calc R
H13D H 1.0196 0.7648 0.8976 0.095 Uiso 1 1 calc R
C21 C 0.9318(4) 0.7228(4) 1.0028(4) 0.0628(10) Uani 1 1 d .
H21A H 0.8501 0.6930 1.0002 0.075 Uiso 1 1 calc R
H21B H 0.9691 0.8072 1.0799 0.075 Uiso 1 1 calc R
C22 C 0.9854(7) 0.6264(8) 1.0006(9) 0.141(3) Uani 1 1 d D
C23 C 0.9658(9) 0.5709(10) 1.0734(9) 0.080(2) Uani 0.55 1 d PD
C23' C 0.9583(13) 0.5050(12) 0.9191(11) 0.090(3) Uani 0.45 1 d PD
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N4 C1 N6 113.1(3) . .
N1 C2 N2 114.6(3) . .
O1 C3 N2 125.5(3) . .
O1 C3 N3 125.6(3) . .
N2 C3 N3 108.9(3) . .
N5 C4 N3 114.6(3) . .
O2 C5 N4 126.7(3) . .
O2 C5 N5 125.6(3) . .
N4 C5 N5 107.6(3) . .
O3 C6 N6 125.9(3) . .
O3 C6 N7 125.7(3) . 2_767
N6 C6 N7 108.4(3) . 2_767
N8 C8 N2 112.9(2) . .
N8 C8 C7 111.0(3) . .
N2 C8 C7 112.3(3) . .
N8 C8 C10 102.2(2) . .
N2 C8 C10 102.1(2) . .
C7 C8 C10 115.8(3) . .
N3 C10 N9 112.4(2) . .
N3 C10 C9 113.1(3) . .
N9 C10 C9 111.1(3) . .
N3 C10 C8 102.6(2) . .
N9 C10 C8 101.9(2) . .
C9 C10 C8 115.0(2) . .
N10 C11 N5 114.2(3) . .
N10 C11 C12 103.2(2) . .
N5 C11 C12 103.5(2) . .
N4 C12 N11 114.7(2) . .
N4 C12 C11 103.0(3) . .
N11 C12 C11 103.4(2) . .
N6 C13 N12 114.7(3) . .
N6 C13 C20 102.8(3) . 2_767
N12 C13 C20 103.0(3) . 2_767
N8 C14 N7 113.9(3) . .
O4 C15 N9 125.8(3) . .
O4 C15 N8 124.9(3) . .
N9 C15 N8 109.3(3) . .
N10 C16 N9 114.3(2) . .
O5 C17 N10 126.2(3) . .
O5 C17 N11 125.7(3) . .
N10 C17 N11 108.1(3) . .
N11 C18 N12 113.3(3) . .
O6 C19 N12 126.6(3) . .
O6 C19 N1 125.9(3) . 2_767
N12 C19 N1 107.4(3) . 2_767
N7 C20 N1 114.5(3) . .
N7 C20 C13 103.5(3) . 2_767
N1 C20 C13 103.6(3) . 2_767
C19 N1 C2 124.3(3) 2_767 .
C19 N1 C20 112.5(3) 2_767 .
C2 N1 C20 123.1(3) . .
C3 N2 C2 120.7(3) . .
C3 N2 C8 113.2(3) . .
C2 N2 C8 125.4(3) . .
C3 N3 C4 120.5(3) . .
C3 N3 C10 113.3(3) . .
C4 N3 C10 126.0(3) . .
C5 N4 C12 113.0(3) . .
C5 N4 C1 122.8(3) . .
C12 N4 C1 122.3(3) . .
C5 N5 C4 122.7(3) . .
C5 N5 C11 112.0(3) . .
C4 N5 C11 123.2(3) . .
C6 N6 C13 112.8(3) . .
C6 N6 C1 122.5(3) . .
C13 N6 C1 123.5(3) . .
C6 N7 C20 111.7(3) 2_767 .
C6 N7 C14 121.1(3) 2_767 .
C20 N7 C14 121.6(3) . .
C15 N8 C14 121.3(3) . .
C15 N8 C8 113.3(2) . .
C14 N8 C8 125.4(3) . .
C15 N9 C16 120.8(3) . .
C15 N9 C10 113.3(2) . .
C16 N9 C10 125.8(3) . .
C17 N10 C11 113.0(3) . .
C17 N10 C16 122.2(3) . .
C11 N10 C16 123.0(3) . .
C17 N11 C18 122.5(3) . .
C17 N11 C12 112.0(2) . .
C18 N11 C12 122.7(3) . .
C19 N12 C18 122.3(3) . .
C19 N12 C13 112.7(3) . .
C18 N12 C13 122.2(3) . .
O8 N14 O9 126.1(10) . .
O8 N14 O7 117.5(9) . .
O9 N14 O7 115.1(8) . .
O1W' O1W O1W" 148.2(10) . .
N13 C21 C22 110.1(5) . .
C23' C22 C23 78.5(7) . .
C23' C22 C21 129.1(9) . .
C23 C22 C21 123.4(8) . .
C22 C23 C23' 118.1(9) . 2_767
C22 C23 C23' 47.6(5) . .
C23' C23 C23' 90.4(7) 2_767 .
C22 C23' C23 120.3(11) . 2_767
C22 C23' C23 53.9(6) . .
C23 C23' C23 89.6(7) 2_767 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N4 1.450(4) .
C1 N6 1.456(4) .
C2 N1 1.442(4) .
C2 N2 1.451(4) .
C3 O1 1.220(4) .
C3 N2 1.361(4) .
C3 N3 1.370(4) .
C4 N5 1.442(4) .
C4 N3 1.449(4) .
C5 O2 1.213(4) .
C5 N4 1.362(4) .
C5 N5 1.379(4) .
C6 O3 1.223(4) .
C6 N6 1.354(4) .
C6 N7 1.369(4) 2_767
C7 C8 1.518(4) .
C8 N8 1.466(4) .
C8 N2 1.467(4) .
C8 C10 1.598(4) .
C9 C10 1.517(4) .
C10 N3 1.451(4) .
C10 N9 1.473(4) .
C11 N10 1.439(4) .
C11 N5 1.444(4) .
C11 C12 1.551(4) .
C12 N4 1.444(4) .
C12 N11 1.451(4) .
C13 N6 1.447(4) .
C13 N12 1.451(4) .
C13 C20 1.547(5) 2_767
C14 N8 1.445(4) .
C14 N7 1.452(4) .
C15 O4 1.226(4) .
C15 N9 1.353(4) .
C15 N8 1.359(4) .
C16 N10 1.441(4) .
C16 N9 1.449(4) .
C17 O5 1.218(4) .
C17 N10 1.367(4) .
C17 N11 1.373(4) .
C18 N11 1.437(4) .
C18 N12 1.451(4) .
C19 O6 1.209(4) .
C19 N12 1.372(4) .
C19 N1 1.379(4) 2_767
C20 N7 1.446(4) .
C20 N1 1.447(5) .
C20 C13 1.547(5) 2_767
N1 C19 1.379(4) 2_767
N7 C6 1.369(4) 2_767
N14 O8 1.185(6) .
N14 O9 1.191(6) .
N14 O7 1.267(8) .
O1W O1W' 1.332(19) .
O1W O1W" 1.480(18) .
N13 C21 1.471(5) .
C21 C22 1.493(8) .
C22 C23' 1.271(12) .
C22 C23 1.392(10) .
C23 C23' 1.510(15) 2_767
C23 C23' 1.687(15) .
C23' C23 1.510(15) 2_767
