#------------------------------------------------------------------------------
#$Date: 2016-03-21 05:29:08 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178480 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/01/4030138.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_4030138
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            'C50 H86 N28 O26'
_chemical_formula_weight         1495.47
_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                94.292(4)
_cell_angle_beta                 111.107(3)
_cell_angle_gamma                104.547(4)
_cell_formula_units_Z            1
_cell_length_a                   11.6609(12)
_cell_length_b                   12.2150(13)
_cell_length_c                   12.4769(13)
_cell_measurement_reflns_used    4578
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.23
_cell_measurement_theta_min      2.21
_cell_volume                     1577.7(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      296(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_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  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17139
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.75
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.9662
_exptl_absorpt_correction_T_min  0.9565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             790
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.894
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         5975
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0679
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1687P)²+0.4256P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2144
_refine_ls_wR_factor_ref         0.2481
_reflns_number_gt                4196
_reflns_number_total             5975
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502255x_si_006.cif
_cod_data_source_block           TMeQ[6]+C10
_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               4030138
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
O6 O 0.5962(2) 0.47381(19) 0.1565(2) 0.0452(6) Uani 1 1 d .
O5 O 0.5312(2) 0.7989(2) 0.78683(19) 0.0460(6) Uani 1 1 d .
O4 O 0.9635(2) 0.6335(2) 0.7064(2) 0.0456(6) Uani 1 1 d .
O3 O 0.8425(2) 0.69430(19) 0.4020(2) 0.0465(6) Uani 1 1 d .
O2 O 0.4231(2) 0.8551(2) 0.4980(2) 0.0483(6) Uani 1 1 d .
O1 O 0.8337(2) 0.3656(2) 0.7541(2) 0.0468(6) Uani 1 1 d .
N12 N 0.8768(2) 0.7837(2) 0.7083(2) 0.0362(6) Uani 1 1 d .
N11 N 0.6797(2) 0.7759(2) 0.3250(2) 0.0346(6) Uani 1 1 d .
N10 N 0.5132(2) 0.8389(2) 0.3634(2) 0.0373(6) Uani 1 1 d .
N9 N 0.6417(2) 0.8976(2) 0.5502(2) 0.0357(6) Uani 1 1 d .
N8 N 0.7949(2) 0.4834(2) 0.8809(2) 0.0389(6) Uani 1 1 d .
N7 N 0.3497(2) 0.6865(2) 0.2070(2) 0.0358(6) Uani 1 1 d .
N6 N 0.8780(2) 0.6717(2) 0.8405(2) 0.0379(6) Uani 1 1 d .
N5 N 0.5158(2) 0.6277(2) 0.1633(2) 0.0360(6) Uani 1 1 d .
N4 N 0.7090(2) 0.7371(2) 0.8722(2) 0.0371(6) Uani 1 1 d .
N3 N 0.7125(2) 0.8534(2) 0.7449(2) 0.0366(6) Uani 1 1 d .
N2 N 0.8073(2) 0.8313(2) 0.5130(2) 0.0360(6) Uani 1 1 d .
N1 N 0.3790(2) 0.4519(2) 0.0953(2) 0.0371(6) Uani 1 1 d .
C20 C 0.8410(3) 0.7659(3) 0.8815(2) 0.0351(6) Uani 1 1 d .
H20A H 0.9019 0.8056 0.9604 0.042 Uiso 1 1 calc R
C19 C 0.7822(3) 0.7597(2) 0.4118(3) 0.0347(7) Uani 1 1 d .
C18 C 0.6369(3) 0.7187(3) 0.2054(3) 0.0377(7) Uani 1 1 d .
H18A H 0.6285 0.7756 0.1551 0.045 Uiso 1 1 calc R
H18B H 0.7027 0.6866 0.1988 0.045 Uiso 1 1 calc R
C17 C 0.9116(2) 0.6899(2) 0.7468(3) 0.0349(7) Uani 1 1 d .
C16 C 0.5161(3) 0.8623(2) 0.4731(3) 0.0346(6) Uani 1 1 d .
C15 C 0.6390(3) 0.7960(2) 0.7992(2) 0.0347(7) Uani 1 1 d .
C14 C 0.8424(3) 0.8453(2) 0.7905(2) 0.0334(6) Uani 1 1 d .
H14A H 0.9057 0.9210 0.8270 0.040 Uiso 1 1 calc R
C13 C 0.9139(3) 0.8353(3) 0.6206(3) 0.0373(7) Uani 1 1 d .
H13A H 0.9692 0.7964 0.6020 0.045 Uiso 1 1 calc R
H13B H 0.9641 0.9150 0.6535 0.045 Uiso 1 1 calc R
C12 C 0.3910(3) 0.6472(3) 0.1178(2) 0.0349(6) Uani 1 1 d .
H12A H 0.3856 0.6974 0.0596 0.042 Uiso 1 1 calc R
C11 C 0.9061(3) 0.5817(3) 0.9063(3) 0.0396(7) Uani 1 1 d .
H11A H 0.9710 0.5561 0.8892 0.048 Uiso 1 1 calc R
H11B H 0.9420 0.6137 0.9891 0.048 Uiso 1 1 calc R
C10 C 0.7662(3) 0.3854(3) 0.8037(3) 0.0369(7) Uani 1 1 d .
C9 C 0.6640(3) 0.6710(2) 0.9477(3) 0.0366(7) Uani 1 1 d .
H9A H 0.5933 0.6940 0.9558 0.044 Uiso 1 1 calc R
H9B H 0.7330 0.6881 1.0246 0.044 Uiso 1 1 calc R
C8 C 0.6409(3) 0.8730(2) 0.3596(3) 0.0342(6) Uani 1 1 d .
C7 C 0.5066(3) 0.5130(3) 0.1414(2) 0.0353(7) Uani 1 1 d .
C6 C 0.6744(3) 0.9355(3) 0.6729(3) 0.0385(7) Uani 1 1 d .
H6A H 0.7442 1.0070 0.7003 0.046 Uiso 1 1 calc R
H6B H 0.6006 0.9510 0.6822 0.046 Uiso 1 1 calc R
C5 C 0.7041(3) 0.4754(2) 0.9369(2) 0.0343(6) Uani 1 1 d .
H5A H 0.7471 0.4847 1.0219 0.041 Uiso 1 1 calc R
C4 C 0.7333(3) 0.9136(2) 0.4943(2) 0.0329(6) Uani 1 1 d .
C3 C 0.3925(3) 0.8067(3) 0.2620(3) 0.0408(7) Uani 1 1 d .
H3A H 0.4020 0.8542 0.2050 0.049 Uiso 1 1 calc R
H3B H 0.3266 0.8225 0.2854 0.049 Uiso 1 1 calc R
C2 C 0.8213(3) 1.0356(3) 0.5273(3) 0.0479(8) Uani 1 1 d .
H2A H 0.8734 1.0526 0.6096 0.072 Uiso 1 1 calc R
H2B H 0.7706 1.0878 0.5088 0.072 Uiso 1 1 calc R
H2C H 0.8759 1.0442 0.4845 0.072 Uiso 1 1 calc R
C1 C 0.6503(4) 0.9653(3) 0.2856(3) 0.0512(8) Uani 1 1 d .
H1A H 0.5917 0.9341 0.2060 0.077 Uiso 1 1 calc R
H1B H 0.7367 0.9914 0.2892 0.077 Uiso 1 1 calc R
H1C H 0.6285 1.0287 0.3147 0.077 Uiso 1 1 calc R
O3W O 0.0690(3) 0.8234(3) 0.1685(3) 0.0765(9) Uani 1 1 d .
O2W O -0.1297(3) 0.9019(3) 0.1894(4) 0.0932(11) Uani 1 1 d .
O1W O 0.9035(3) 0.5653(3) 0.2376(3) 0.0732(9) Uani 1 1 d .
N13 N 0.7621(3) 0.3352(3) 0.2524(3) 0.0618(8) Uani 1 1 d .
H13C H 0.7563 0.2772 0.2011 0.093 Uiso 1 1 calc R
H13D H 0.8260 0.3962 0.2579 0.093 Uiso 1 1 calc R
H13E H 0.6884 0.3527 0.2286 0.093 Uiso 1 1 calc R
C21 C 0.5511(6) 0.5414(5) 0.5039(7) 0.117(2) Uani 1 1 d .
H21A H 0.5679 0.6040 0.5654 0.140 Uiso 1 1 calc R
H21B H 0.5305 0.5705 0.4312 0.140 Uiso 1 1 calc R
C22 C 0.6735(6) 0.5080(6) 0.5285(6) 0.111(2) Uani 1 1 d .
H22A H 0.7429 0.5772 0.5406 0.133 Uiso 1 1 calc R
H22B H 0.6938 0.4791 0.6013 0.133 Uiso 1 1 calc R
C23 C 0.6726(4) 0.4252(4) 0.4425(4) 0.0729(12) Uani 1 1 d .
H23A H 0.6443 0.4510 0.3683 0.087 Uiso 1 1 calc R
H23B H 0.6082 0.3540 0.4356 0.087 Uiso 1 1 calc R
C24 C 0.7977(5) 0.3981(5) 0.4606(4) 0.0841(15) Uani 1 1 d .
H24A H 0.8298 0.3773 0.5371 0.101 Uiso 1 1 calc R
H24B H 0.8606 0.4674 0.4609 0.101 Uiso 1 1 calc R
C25 C 0.7883(5) 0.3007(5) 0.3687(5) 0.0906(17) Uani 1 1 d .
H25A H 0.8684 0.2811 0.3942 0.109 Uiso 1 1 calc R
H25B H 0.7198 0.2328 0.3620 0.109 Uiso 1 1 calc R
N01 N 0.8164(4) 0.1385(4) 0.0464(4) 0.0752(10) Uani 1 1 d .
O03 O 0.8120(4) 0.2281(4) 0.0088(4) 0.1057(13) Uani 1 1 d .
O02 O 0.8472(5) 0.0638(4) 0.0011(4) 0.1231(15) Uani 1 1 d .
O01 O 0.7960(4) 0.1239(4) 0.1365(4) 0.1087(13) Uani 1 1 d .
O4W O 0.4893(5) 0.8757(4) 0.9818(4) 0.1234(16) Uani 1 1 d .
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
C17 N12 C13 121.7(2) . .
C17 N12 C14 111.9(2) . .
C13 N12 C14 123.0(3) . .
C19 N11 C18 121.0(2) . .
C19 N11 C8 113.3(2) . .
C18 N11 C8 124.2(2) . .
C16 N10 C3 120.7(2) . .
C16 N10 C8 113.1(2) . .
C3 N10 C8 125.0(3) . .
C16 N9 C6 120.3(2) . .
C16 N9 C4 113.7(2) . .
C6 N9 C4 124.9(2) . .
C10 N8 C11 123.2(2) . .
C10 N8 C5 112.4(2) . .
C11 N8 C5 124.3(2) . .
C10 N7 C3 121.2(2) 2_666 .
C10 N7 C12 111.6(2) 2_666 .
C3 N7 C12 121.9(2) . .
C17 N6 C20 112.4(2) . .
C17 N6 C11 122.4(2) . .
C20 N6 C11 123.6(2) . .
C7 N5 C12 112.1(2) . .
C7 N5 C18 123.1(2) . .
C12 N5 C18 123.7(2) . .
C15 N4 C9 123.3(2) . .
C15 N4 C20 112.5(2) . .
C9 N4 C20 123.2(3) . .
C15 N3 C6 122.5(2) . .
C15 N3 C14 112.5(2) . .
C6 N3 C14 123.3(2) . .
C19 N2 C13 120.9(2) . .
C19 N2 C4 113.0(2) . .
C13 N2 C4 125.1(2) . .
C7 N1 C5 112.6(2) . 2_666
C7 N1 C9 121.5(2) . 2_666
C5 N1 C9 123.4(2) 2_666 2_666
N6 C20 N4 115.2(2) . .
N6 C20 C14 103.2(2) . .
N4 C20 C14 103.1(2) . .
O3 C19 N11 126.3(3) . .
O3 C19 N2 125.4(3) . .
N11 C19 N2 108.2(2) . .
N5 C18 N11 114.6(2) . .
O4 C17 N12 126.4(3) . .
O4 C17 N6 125.9(3) . .
N12 C17 N6 107.6(2) . .
O2 C16 N10 126.0(3) . .
O2 C16 N9 125.8(3) . .
N10 C16 N9 108.2(2) . .
O5 C15 N4 126.0(3) . .
O5 C15 N3 126.1(3) . .
N4 C15 N3 107.9(2) . .
N3 C14 N12 115.3(2) . .
N3 C14 C20 103.5(2) . .
N12 C14 C20 103.5(2) . .
N12 C13 N2 114.8(2) . .
N5 C12 N7 114.5(2) . .
N5 C12 C5 103.6(2) . 2_666
N7 C12 C5 103.2(2) . 2_666
N8 C11 N6 113.7(2) . .
O1 C10 N8 125.4(3) . .
O1 C10 N7 126.2(3) . 2_666
N8 C10 N7 108.5(2) . 2_666
N4 C9 N1 112.9(2) . 2_666
N11 C8 N10 113.3(2) . .
N11 C8 C1 113.0(2) . .
N10 C8 C1 110.4(3) . .
N11 C8 C4 102.5(2) . .
N10 C8 C4 102.4(2) . .
C1 C8 C4 114.7(2) . .
O6 C7 N1 126.2(3) . .
O6 C7 N5 125.9(3) . .
N1 C7 N5 107.8(2) . .
N3 C6 N9 113.8(2) . .
N1 C5 N8 115.7(2) 2_666 .
N1 C5 C12 102.8(2) 2_666 2_666
N8 C5 C12 103.1(2) . 2_666
N9 C4 N2 113.9(2) . .
N9 C4 C2 112.0(2) . .
N2 C4 C2 110.9(2) . .
N9 C4 C8 102.1(2) . .
N2 C4 C8 102.2(2) . .
C2 C4 C8 115.2(3) . .
N10 C3 N7 113.6(2) . .
C21 C21 C22 115.9(8) 2_666 .
C23 C22 C21 117.0(6) . .
C22 C23 C24 117.8(5) . .
C23 C24 C25 115.4(4) . .
N13 C25 C24 111.5(4) . .
O03 N01 O02 121.9(5) . .
O03 N01 O01 120.0(5) . .
O02 N01 O01 118.1(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O6 C7 1.217(3) .
O5 C15 1.220(3) .
O4 C17 1.214(3) .
O3 C19 1.215(3) .
O2 C16 1.216(3) .
O1 C10 1.219(3) .
N12 C17 1.372(4) .
N12 C13 1.446(4) .
N12 C14 1.453(3) .
N11 C19 1.364(4) .
N11 C18 1.448(4) .
N11 C8 1.459(3) .
N10 C16 1.364(4) .
N10 C3 1.450(4) .
N10 C8 1.461(4) .
N9 C16 1.365(4) .
N9 C6 1.446(4) .
N9 C4 1.454(3) .
N8 C10 1.366(4) .
N8 C11 1.446(4) .
N8 C5 1.452(4) .
N7 C10 1.367(4) 2_666
N7 C3 1.453(4) .
N7 C12 1.457(4) .
N6 C17 1.377(4) .
N6 C20 1.446(4) .
N6 C11 1.453(4) .
N5 C7 1.376(4) .
N5 C12 1.448(4) .
N5 C18 1.448(4) .
N4 C15 1.367(4) .
N4 C9 1.440(4) .
N4 C20 1.449(4) .
N3 C15 1.369(4) .
N3 C6 1.442(4) .
N3 C14 1.445(4) .
N2 C19 1.373(4) .
N2 C13 1.452(4) .
N2 C4 1.462(4) .
N1 C7 1.365(4) .
N1 C5 1.446(4) 2_666
N1 C9 1.449(4) 2_666
C20 C14 1.548(4) .
C12 C5 1.551(4) 2_666
C10 N7 1.367(4) 2_666
C9 N1 1.449(4) 2_666
C8 C1 1.516(5) .
C8 C4 1.592(4) .
C5 N1 1.446(4) 2_666
C5 C12 1.551(4) 2_666
C4 C2 1.510(4) .
N13 C25 1.488(6) .
C21 C21 1.323(13) 2_666
C21 C22 1.514(9) .
C22 C23 1.414(7) .
C23 C24 1.519(6) .
C24 C25 1.544(7) .
N01 O03 1.228(5) .
N01 O02 1.230(5) .
N01 O01 1.246(5) .
