#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:20:53 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178895 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/24/4112436.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_4112436
loop_
_publ_author_name
'Milya G. Davlieva'
'Jian-Ming Lü'
'Sergey V. Lindeman'
'Jay K. Kochi'
_publ_section_title
;
 Crystallographic Distinction between "Contact" and "Separated" Ion Pairs:
 Structural Effects on Electronic/ESR Spectra of Alkali-Metal
 Nitrobenzenides
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4557
_journal_page_last               4565
_journal_paper_doi               10.1021/ja049856k
_journal_volume                  126
_journal_year                    2004
_chemical_compound_source        'chemical synthesis'
_chemical_formula_sum            'C24 H41 K N3 O8'
_chemical_formula_weight         538.70
_chemical_name_systematic
; 
 Potassium [2.2.2]cryptand nitrobenzenide 
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 98.0220(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.7997(8)
_cell_length_b                   10.1130(5)
_cell_length_c                   17.4795(9)
_cell_measurement_reflns_used    8652
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      2
_cell_volume                     2765.6(2)
_computing_cell_refinement       'SAINT V6.28 (BrukerAXS, 1997-2001)'
_computing_data_collection       'SMART V5.625 (BrukerAXS, 1997-2001)'
_computing_data_reduction        'SAINT & SADABS V2.06 (Sheldrick, 2000)'
_computing_molecular_graphics    'XP V5.06 (BrukerAXS, 1997-99)'
_computing_publication_material  'SHELXL-93, XCIF V5.05 (BrukerAXS, 1997-99)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measurement_device       'Siemens SMART'
_diffrn_measurement_method
;
ω-scan, frame range 0.3 deg, hemisphere
;
_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  0.0171
_diffrn_reflns_av_sigmaI/netI    0.0162
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            29934
_diffrn_reflns_theta_max         31.71
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.813
_exptl_absorpt_correction_type   'Semi-empirical (SADABS procedure)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    none
_exptl_crystal_description       prism
_exptl_crystal_F_000             1156
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.025
_refine_ls_goodness_of_fit_obs   1.046
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         8835
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_restrained_S_obs      1.046
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_obs          0.0389
_refine_ls_shift/esd_max         0.025
_refine_ls_shift/esd_mean        0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0692P)²+0.3996P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1129
_refine_ls_wR_factor_obs         0.1042
_reflns_number_observed          7867
_reflns_number_total             8851
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ja049856krom20040109_111831.cif
_cod_data_source_block           milnsx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0692P)^2^+0.3996P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0692P)^2^+0.3996P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               4112436
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
K1 K 0.834557(11) 0.33542(2) 0.072461(10) 0.02548(6) Uani 1 d
O1 O 0.55698(5) 0.82358(9) 0.15200(5) 0.0478(2) Uani 1 d
O2 O 0.47114(6) 0.75386(10) 0.23596(6) 0.0566(3) Uani 1 d
N1 N 0.48466(6) 0.82667(9) 0.17842(5) 0.0353(2) Uani 1 d
C1 C 0.42054(6) 0.91115(9) 0.14635(5) 0.0283(2) Uani 1 d
C2 C 0.34258(6) 0.91663(11) 0.17672(6) 0.0353(2) Uani 1 d
C3 C 0.27950(7) 1.00166(13) 0.14411(8) 0.0467(3) Uani 1 d
C4 C 0.29123(8) 1.08033(14) 0.08070(9) 0.0547(3) Uani 1 d
C5 C 0.36855(8) 1.07375(13) 0.05107(7) 0.0471(3) Uani 1 d
C6 C 0.43316(7) 0.99158(10) 0.08350(6) 0.0342(2) Uani 1 d
N2 N 0.67662(5) 0.47425(8) -0.00425(4) 0.02720(14) Uani 1 d
N3 N 0.99678(6) 0.20094(10) 0.14834(5) 0.0382(2) Uani 1 d
O11 O 0.77259(4) 0.56386(6) 0.14043(4) 0.02695(13) Uani 1 d
O12 O 0.93702(4) 0.45552(7) 0.19519(4) 0.03045(14) Uani 1 d
O21 O 0.67829(5) 0.21340(8) 0.06808(5) 0.0384(2) Uani 1 d
O22 O 0.82385(5) 0.10518(7) 0.16282(5) 0.0389(2) Uani 1 d
O31 O 0.82499(4) 0.42265(8) -0.08541(4) 0.0350(2) Uani 1 d
O32 O 0.95938(5) 0.25258(8) -0.01853(4) 0.0384(2) Uani 1 d
C11 C 0.64810(6) 0.57513(10) 0.04705(5) 0.0297(2) Uani 1 d
C12 C 0.72039(6) 0.65254(9) 0.09134(6) 0.0297(2) Uani 1 d
C13 C 0.83687(6) 0.63187(10) 0.19087(5) 0.0299(2) Uani 1 d
C14 C 0.88850(6) 0.53386(10) 0.24161(5) 0.0316(2) Uani 1 d
C15 C 1.00362(7) 0.38764(14) 0.24190(6) 0.0410(2) Uani 1 d
C16 C 1.05094(7) 0.30124(14) 0.19155(7) 0.0438(2) Uani 1 d
C21 C 0.61087(6) 0.37222(11) -0.02192(6) 0.0362(2) Uani 1 d
C22 C 0.60101(7) 0.28367(12) 0.04565(7) 0.0406(2) Uani 1 d
C23 C 0.67250(8) 0.12799(15) 0.13215(8) 0.0503(3) Uani 1 d
C24 C 0.74605(10) 0.03472(13) 0.14054(9) 0.0529(3) Uani 1 d
C25 C 0.89572(10) 0.01896(12) 0.16950(8) 0.0497(3) Uani 1 d
C26 C 0.97507(8) 0.09479(14) 0.20013(8) 0.0476(3) Uani 1 d
C31 C 0.69509(7) 0.53824(12) -0.07547(5) 0.0368(2) Uani 1 d
C32 C 0.74286(7) 0.45194(14) -0.12562(6) 0.0412(2) Uani 1 d
C33 C 0.87050(8) 0.33602(13) -0.12964(6) 0.0414(2) Uani 1 d
C34 C 0.96010(7) 0.32019(13) -0.09016(6) 0.0415(2) Uani 1 d
C35 C 1.04369(7) 0.23264(15) 0.01913(7) 0.0452(3) Uani 1 d
C36 C 1.04100(9) 0.14304(15) 0.08778(8) 0.0503(3) Uani 1 d
H2A H 0.3329(9) 0.8596(14) 0.2225(8) 0.041(4) Uiso 1 d
H3A H 0.2252(10) 1.0064(16) 0.1683(9) 0.052(4) Uiso 1 d
H4A H 0.2421(10) 1.1383(15) 0.0519(8) 0.043(4) Uiso 1 d
H5A H 0.3760(11) 1.1269(17) 0.0047(10) 0.056(4) Uiso 1 d
H6A H 0.4877(9) 0.9874(15) 0.0620(8) 0.042(3) Uiso 1 d
H11A H 0.6164(8) 0.5346(12) 0.0824(7) 0.028(3) Uiso 1 d
H11B H 0.6102(9) 0.6362(14) 0.0173(8) 0.040(3) Uiso 1 d
H12A H 0.7567(9) 0.6954(14) 0.0575(8) 0.040(3) Uiso 1 d
H12B H 0.6965(9) 0.7176(15) 0.1213(8) 0.039(3) Uiso 1 d
H13A H 0.8125(9) 0.6944(14) 0.2232(8) 0.037(3) Uiso 1 d
H13B H 0.8716(9) 0.6782(13) 0.1600(8) 0.034(3) Uiso 1 d
H14A H 0.9255(9) 0.5814(15) 0.2810(9) 0.044(4) Uiso 1 d
H14B H 0.8503(9) 0.4745(13) 0.2665(7) 0.036(3) Uiso 1 d
H15A H 0.9791(10) 0.3355(14) 0.2782(9) 0.045(4) Uiso 1 d
H15B H 1.0424(11) 0.4535(17) 0.2693(10) 0.059(5) Uiso 1 d
H16A H 1.0766(11) 0.3633(16) 0.1544(10) 0.052(4) Uiso 1 d
H16B H 1.1010(12) 0.2621(19) 0.2256(11) 0.067(5) Uiso 1 d
H21A H 0.6249(10) 0.3126(15) -0.0632(9) 0.045(4) Uiso 1 d
H21B H 0.5534(9) 0.4108(15) -0.0410(8) 0.043(4) Uiso 1 d
H22A H 0.5877(9) 0.3315(13) 0.0897(8) 0.039(3) Uiso 1 d
H22B H 0.5521(11) 0.2201(18) 0.0312(10) 0.058(4) Uiso 1 d
H23A H 0.6211(13) 0.0724(20) 0.1235(11) 0.073(5) Uiso 1 d
H23B H 0.6756(11) 0.1790(17) 0.1823(10) 0.056(4) Uiso 1 d
H24A H 0.7382(12) -0.0342(19) 0.1782(11) 0.064(5) Uiso 1 d
H24B H 0.7487(10) -0.0101(17) 0.0933(10) 0.053(4) Uiso 1 d
H25A H 0.8992(10) -0.0168(17) 0.1162(10) 0.055(4) Uiso 1 d
H25B H 0.8897(12) -0.0553(18) 0.2076(10) 0.066(5) Uiso 1 d
H26A H 0.9668(10) 0.1360(15) 0.2481(9) 0.044(4) Uiso 1 d
H26B H 1.0217(12) 0.0310(19) 0.2098(10) 0.066(5) Uiso 1 d
H31A H 0.7284(9) 0.6177(15) -0.0631(8) 0.039(3) Uiso 1 d
H31B H 0.6419(10) 0.5688(15) -0.1074(9) 0.047(4) Uiso 1 d
H32A H 0.7145(10) 0.3675(16) -0.1397(9) 0.044(4) Uiso 1 d
H32B H 0.7504(11) 0.5048(17) -0.1723(10) 0.058(4) Uiso 1 d
H33A H 0.8725(11) 0.3716(17) -0.1799(10) 0.057(4) Uiso 1 d
H33B H 0.8412(10) 0.2478(16) -0.1334(9) 0.050(4) Uiso 1 d
H34A H 0.9905(11) 0.2664(16) -0.1269(10) 0.054(4) Uiso 1 d
H34B H 0.9892(11) 0.4117(18) -0.0799(10) 0.055(4) Uiso 1 d
H35A H 1.0681(11) 0.3204(17) 0.0324(9) 0.049(4) Uiso 1 d
H35B H 1.0766(12) 0.1872(17) -0.0140(10) 0.059(5) Uiso 1 d
H36A H 1.0115(13) 0.0589(22) 0.0680(12) 0.075(6) Uiso 1 d
H36B H 1.1025(12) 0.1229(19) 0.1093(11) 0.066(5) Uiso 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'
K K 0.2009 0.2494 '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
O21 K1 O12 129.87(2)
O21 K1 O32 123.02(3)
O12 K1 O32 100.76(2)
O21 K1 O22 61.55(2)
O12 K1 O22 90.14(2)
O32 K1 O22 99.83(2)
O21 K1 O11 90.92(2)
O12 K1 O11 61.21(2)
O32 K1 O11 141.83(2)
O22 K1 O11 112.67(2)
O21 K1 O31 100.59(2)
O12 K1 O31 123.54(2)
O32 K1 O31 59.96(2)
O22 K1 O31 141.88(2)
O11 K1 O31 100.19(2)
O21 K1 N2 60.79(2)
O12 K1 N2 119.82(2)
O32 K1 N2 119.17(2)
O22 K1 N2 121.44(2)
O11 K1 N2 59.55(2)
O31 K1 N2 60.07(2)
O21 K1 N3 120.69(3)
O12 K1 N3 59.58(2)
O32 K1 N3 60.05(2)
O22 K1 N3 60.06(3)
O11 K1 N3 120.11(2)
O31 K1 N3 118.92(2)
N2 K1 N3 178.50(2)
O2 N1 O1 121.12(9)
O2 N1 C1 118.53(8)
O1 N1 C1 120.33(8)
N1 C1 C6 119.95(9)
N1 C1 C2 120.08(8)
C6 C1 C2 119.97(9)
C3 C2 C1 119.24(10)
C2 C3 C4 121.00(11)
C5 C4 C3 119.19(11)
C6 C5 C4 120.95(10)
C5 C6 C1 119.63(10)
C21 N2 C31 110.52(8)
C21 N2 C11 110.39(7)
C31 N2 C11 108.99(8)
C21 N2 K1 106.53(6)
C31 N2 K1 109.44(5)
C11 N2 K1 110.95(5)
C16 N3 C36 110.17(10)
C16 N3 C26 110.87(10)
C36 N3 C26 109.08(10)
C16 N3 K1 108.13(6)
C36 N3 K1 108.72(7)
C26 N3 K1 109.84(6)
C12 O11 C13 111.84(7)
C12 O11 K1 117.79(5)
C13 O11 K1 113.24(5)
C15 O12 C14 110.81(7)
C15 O12 K1 122.61(7)
C14 O12 K1 112.28(5)
C22 O21 C23 111.89(9)
C22 O21 K1 121.13(6)
C23 O21 K1 113.89(6)
C25 O22 C24 111.31(10)
C25 O22 K1 116.13(7)
C24 O22 K1 112.00(7)
C32 O31 C33 110.80(8)
C32 O31 K1 117.44(6)
C33 O31 K1 111.58(6)
C35 O32 C34 110.72(8)
C35 O32 K1 117.74(6)
C34 O32 K1 116.28(6)
N2 C11 C12 113.52(7)
O11 C12 C11 108.46(7)
O11 C13 C14 109.26(8)
O12 C14 C13 108.79(7)
O12 C15 C16 109.44(8)
N3 C16 C15 113.55(9)
N2 C21 C22 113.63(8)
O21 C22 C21 109.56(8)
O21 C23 C24 109.04(11)
O22 C24 C23 109.97(10)
O22 C25 C26 109.44(10)
N3 C26 C25 113.99(10)
N2 C31 C32 114.32(9)
O31 C32 C31 109.25(8)
O31 C33 C34 109.39(9)
O32 C34 C33 109.46(9)
O32 C35 C36 109.04(10)
N3 C36 C35 113.75(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
K1 O21 2.7517(7)
K1 O12 2.7801(7)
K1 O32 2.8278(7)
K1 O22 2.8318(8)
K1 O11 2.8341(7)
K1 O31 2.8809(7)
K1 N2 3.0103(8)
K1 N3 3.0380(9)
O1 N1 1.2910(12)
O2 N1 1.2883(12)
N1 C1 1.3828(12)
C1 C6 1.4033(13)
C1 C2 1.4087(13)
C2 C3 1.3782(15)
C3 C4 1.397(2)
C4 C5 1.393(2)
C5 C6 1.376(2)
N2 C21 1.4661(12)
N2 C31 1.4679(12)
N2 C11 1.4700(11)
N3 C16 1.467(2)
N3 C36 1.4689(15)
N3 C26 1.4752(15)
O11 C12 1.4224(11)
O11 C13 1.4254(10)
O12 C15 1.4161(12)
O12 C14 1.4309(11)
O21 C22 1.4197(14)
O21 C23 1.4273(14)
O22 C25 1.424(2)
O22 C24 1.4271(15)
O31 C32 1.4181(13)
O31 C33 1.4273(12)
O32 C35 1.4155(14)
O32 C34 1.4280(13)
C11 C12 1.5067(13)
C13 C14 1.4941(15)
C15 C16 1.510(2)
C21 C22 1.507(2)
C23 C24 1.488(2)
C25 C26 1.503(2)
C31 C32 1.5115(15)
C33 C34 1.494(2)
C35 C36 1.509(2)
