#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/44/2004401.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_2004401
loop_
_publ_author_name
'Bien, J. T.'
'Shang, M.'
'Smith, B. D.'
_publ_section_title
;
 7,7'-Bis[(aza-18-crown-6)carbonyl]thioindigo
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              183
_journal_page_last               186
_journal_paper_doi               10.1107/S0108270195012455
_journal_volume                  52
_journal_year                    1996
_chemical_formula_sum            'C42 H54 N2 O14 S2'
_chemical_formula_weight         875.03
_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_type_scat_source           'Cromer & Waber (1974)'
_cell_angle_alpha                97.29(2)
_cell_angle_beta                 104.51(2)
_cell_angle_gamma                105.49(2)
_cell_formula_units_Z            1
_cell_length_a                   9.267(2)
_cell_length_b                   10.344(3)
_cell_length_c                   12.149(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      14
_cell_measurement_theta_min      12
_cell_volume                     1062.8(5)
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       'ω/2θ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2955
_diffrn_reflns_theta_max         26
_diffrn_standards_decay_%        2.9
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_correction_T_min  0.9671
_exptl_absorpt_correction_type
'empirical via \y scan (North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       plate
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.37(4)
_refine_diff_density_min         -0.24(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   2.256
_refine_ls_hydrogen_treatment
'noref but located from difference Fourier maps'
_refine_ls_number_parameters     298
_refine_ls_number_reflns         1994
_refine_ls_R_factor_obs          0.05085
_refine_ls_shift/esd_max         0.03
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     w=1/σ²(F)
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.06747
_reflns_number_observed          1994
_reflns_number_total             2955
_reflns_observed_criterion       I>3\s(I)
_cod_data_source_file            ka1145.cif
_cod_data_source_block           ka1145a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value ' w=1/\s^2^(F)' 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^(F)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1062.7(5)
_cod_database_code               2004401
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_B_iso_or_equiv
C(1) .5600(4) .5127(3) .4767(3) 3.59(8)
C(2) .6444(4) .4122(3) .4563(3) 3.76(9)
O(1) .6132(3) .2996(2) .4819(2) 5.21(7)
C(3) .7664(4) .4692(3) .4031(3) 3.50(8)
C(4) .8652(4) .4058(4) .3687(3) 4.32(9)
C(5) .9732(4) .4739(4) .3187(3) 4.50(10)
C(6) .9834(4) .6083(4) .3058(3) 4.35(9)
C(7) .8854(4) .6742(3) .3403(3) 3.81(9)
C(8) .7715(4) .6013(3) .3864(3) 3.49(8)
S .63050(10) .66343(9) .43002(9) 4.01(2)
C(9) .8806(4) .8133(4) .3192(3) 4.26(9)
O(2) .7535(3) .8264(3) .2724(3) 6.78(8)
N 1.0129(3) .9212(3) .3529(3) 4.22(7)
C(10) 1.1636(5) .9223(4) .4265(3) 4.80(10)
C(11) 1.2960(5) .9604(4) .3737(4) 5.50(10)
O(3) 1.2560(3) .8719(3) .2652(2) 5.28(7)
C(12) 1.3898(5) .8611(5) .2301(4) 6.80(10)
C(13) 1.4975(5) .9928(5) .2233(5) 7.50(10)
O(4) 1.4198(3) 1.0505(3) .1385(3) 6.71(8)
C(14) 1.5291(6) 1.1636(6) .1180(6) 9.3(2)
C(15) 1.463(2) 1.234(2) .0290(10) 16.5(5)
C(15)' 1.4790(10) 1.2610(10) .0890(10) 10.7(3)
O(5) 1.3700(10) 1.2961(9) .0568(7) 11.2(3)
O(5)' 1.4148(8) 1.3324(6) .1621(6) 8.3(2)
C(16) 1.3880(10) 1.4440(10) .1319(7) 15.0(3)
C(17) 1.2465(7) 1.4557(6) .0572(6) 10.9(2)
O(6) 1.1196(4) 1.4112(4) .1008(3) 9.30(10)
C(18) 1.0410(10) 1.2580(10) .0270(10) 8.9(4)
C(18)' .9760(10) 1.3245(8) .0390(8) 5.7(2)
C(19) .9517(9) 1.1859(5) .0588(5) 10.5(2)
O(7) .9664(4) 1.1759(3) .1758(3) 6.32(8)
C(20) .9969(5) 1.0557(4) .1996(4) 5.50(10)
C(21) .9983(5) 1.0518(4) .3232(4) 4.50(10)
H(4) .856 .307 .383 4.7
H(5) 1.041 .439 .288 4.9
H(6) 1.075 .663 .279 4.8
H(101) 1.155 .841 .438 5.3
H(102) 1.197 .984 .499 5.3
H(111) 1.331 1.059 .366 6.2
H(112) 1.380 .935 .437 6.2
H(121) 1.343 .800 .154 7.4
H(122) 1.439 .807 .293 7.4
H(131) 1.591 .969 .209 8.0
H(132) 1.531 1.086 .315 8.0
H(141) 1.612 1.217 .207 10.3
H(142) 1.608 1.119 .067 10.3
H(161) 1.474 1.474 .096 14.8
H(162) 1.415 1.498 .208 14.8
H(171) 1.224 1.389 -0.021 12.8
H(172) 1.268 1.545 .046 12.8
H(191) 1.038 1.155 .037 11.9
H(192) .835 1.113 -0.014 11.9
H(201) .936 .990 .160 5.9
H(202) 1.113 1.054 .199 5.9
H(211) 1.094 1.120 .389 1.8
H(212) .885 1.072 .335 3.9
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle
_geom_angle_publ_flag
C(1) C(1) C(2) 2_666 123.3(3) yes
C(1) C(1) S 2_666 124.3(3) yes
C(2) C(1) S . 112.4(3) yes
C(1) C(2) O(1) . 123.2(4) yes
C(1) C(2) C(3) . 110.1(3) yes
O(1) C(2) C(3) . 126.7(4) yes
C(2) C(3) C(4) . 127.2(3) yes
C(2) C(3) C(8) . 111.9(3) yes
C(4) C(3) C(8) . 120.9(3) yes
C(3) C(4) C(5) . 119.9(4) yes
C(4) C(5) C(6) . 119.6(4) yes
C(5) C(6) C(7) . 121.4(4) yes
C(6) C(7) C(8) . 118.2(3) yes
C(6) C(7) C(9) . 124.0(4) yes
C(8) C(7) C(9) . 117.5(3) yes
C(3) C(8) C(7) . 119.9(4) yes
C(3) C(8) S . 114.7(3) yes
C(7) C(8) S . 125.5(3) yes
C(1) S C(8) . 91.0(2) yes
C(7) C(9) O(2) . 118.4(3) yes
C(7) C(9) N . 120.6(3) yes
O(2) C(9) N . 121.0(4) yes
C(9) N C(10) . 125.1(3) yes
C(9) N C(21) . 116.9(3) yes
C(10) N C(21) . 117.7(3) yes
C(3) C(4) H(4) . 118.1 no
C(5) C(4) H(4) . 122.0 no
C(4) C(5) H(5) . 127.4 no
C(6) C(5) H(5) . 113.0 no
C(5) C(6) H(6) . 119.1 no
C(7) C(6) H(6) . 119.1 no
N C(10) C(11) . 114.2(3) no
N C(10) H(101) . 107.6 no
N C(10) H(102) . 112.8 no
C(11) C(10) H(101) . 106.6 no
C(11) C(10) H(102) . 105.8 no
H(101) C(10) H(102) . 109.5 no
C(10) C(11) O(3) . 109.5(3) no
C(10) C(11) H(111) . 115.8 no
C(10) C(11) H(112) . 97.1 no
O(3) C(11) H(111) . 110.3 no
O(3) C(11) H(112) . 110.5 no
H(111) C(11) H(112) . 113.0 no
C(11) O(3) C(12) . 113.3(3) no
O(3) C(12) C(13) . 115.1(4) no
O(3) C(12) H(121) . 103.2 no
O(3) C(12) H(122) . 100.9 no
C(13) C(12) H(121) . 110.8 no
C(13) C(12) H(122) . 116.0 no
H(121) C(12) H(122) . 109.8 no
C(12) C(13) O(4) . 110.0(3) no
C(12) C(13) H(131) . 105.0 no
C(12) C(13) H(132) . 111.9 no
O(4) C(13) H(131) . 115.3 no
O(4) C(13) H(132) . 100.7 no
H(131) C(13) H(132) . 114.2 no
C(13) O(4) C(14) . 109.9(3) no
O(4) C(14) C(15) . 115.8(7) no
O(4) C(14) C(15)' . 116.8(7) no
O(4) C(14) H(141) . 104.3 no
O(4) C(14) H(142) . 108.0 no
C(15) C(14) H(141) . 124.8 no
C(15) C(14) H(142) . 97.3 no
C(15)' C(14) H(141) . 99.7 no
C(15)' C(14) H(142) . 120.7 no
H(141) C(14) H(142) . 104.9 no
C(14) C(15) O(5) . 114.0(10) no
C(14) C(15)' O(5) . 146.0(10) no
C(14) C(15)' O(5)' . 121.0(10) no
C(15) O(5) C(16) . 136.4(9) no
C(15)' O(5) C(16) . 112.2(7) no
C(15)' O(5)' C(16) . 115.7(9) no
O(5) C(16) C(17) . 94.1(6) no
O(5) C(16) H(161) . 81.2 no
O(5) C(16) H(162) . 146 no
O(5)' C(16) C(17) . 128.0(7) no
O(5)' C(16) H(161) . 99.3 no
O(5)' C(16) H(162) . 98.1 no
C(17) C(16) H(161) . 108.4 no
C(17) C(16) H(162) . 111 no
H(161) C(16) H(162) . 110.5 no
C(16) C(17) O(6) . 111.2(7) no
C(16) C(17) H(171) . 105.2 no
C(16) C(17) H(172) . 107.5 no
O(6) C(17) H(171) . 108.0 no
O(6) C(17) H(172) . 115.5 no
H(171) C(17) H(172) . 108.9 no
C(17) O(6) C(18) . 100.6(6) no
C(17) O(6) C(18)' . 125.8(6) no
O(6) C(18) C(19) . 117.0(10) no
O(6) C(18) H(191) . 139.2 no
C(18)' C(18) C(19) . 83.0(10) no
C(19) C(18) H(191) . 54.3 no
O(6) C(18)' C(19) . 112.9(7) no
C(18) C(19) O(7) . 125.6(7) no
C(18) C(19) H(191) . 59.8 no
C(18) C(19) H(192) . 116.7 no
C(18)' C(19) O(7) . 114.1(5) no
C(18)' C(19) H(191) . 105.9 no
C(18)' C(19) H(192) . 107.5 no
O(7) C(19) H(191) . 107.1 no
O(7) C(19) H(192) . 117.8 no
H(191) C(19) H(192) . 103.3 no
C(19) O(7) C(20) . 112.3(4) no
O(7) C(20) C(21) . 107.3(4) no
O(7) C(20) H(201) . 113.6 no
O(7) C(20) H(202) . 113.6 no
C(21) C(20) H(201) . 108.7 no
C(21) C(20) H(202) . 103.7 no
H(201) C(20) H(202) . 109.4 no
N C(21) C(20) . 111.5(3) no
N C(21) H(211) . 99.5 no
N C(21) H(212) . 112.6 no
C(20) C(21) H(211) . 117.7 no
C(20) C(21) H(212) . 107.8 no
H(211) C(21) H(212) . 107.7 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C(1) C(1) 2_666 1.350(5) yes
C(1) C(2) . 1.489(5) yes
C(1) S . 1.744(4) yes
C(2) O(1) . 1.221(4) yes
C(2) C(3) . 1.466(5) yes
C(3) C(4) . 1.373(6) yes
C(3) C(8) . 1.397(5) yes
C(4) C(5) . 1.379(6) yes
C(5) C(6) . 1.399(6) yes
C(6) C(7) . 1.384(6) yes
C(7) C(8) . 1.404(5) yes
C(7) C(9) . 1.502(5) yes
C(8) S . 1.764(4) yes
C(9) O(2) . 1.223(5) yes
C(9) N . 1.348(4) yes
N C(10) . 1.454(5) yes
N C(21) . 1.473(5) yes
C(4) H(4) . 1.046 no
C(5) H(5) . 0.934 no
C(6) H(6) . 1.036 no
C(10) C(11) . 1.507(7) no
C(10) H(101) . 0.853 no
C(10) H(102) . 0.942 no
C(11) O(3) . 1.407(5) no
C(11) H(111) . 1.011 no
C(11) H(112) . 1.062 no
O(3) C(12) . 1.434(6) no
C(12) C(13) . 1.483(6) no
C(12) H(121) . 0.974 no
C(12) H(122) . 1.078 no
C(13) O(4) . 1.396(6) no
C(13) H(131) . 1.012 no
C(13) H(132) . 1.285 no
O(4) C(14) . 1.422(6) no
C(14) C(15) . 1.48(2) no
C(14) C(15)' . 1.270(10) no
C(14) H(141) . 1.128 no
C(14) H(142) . 1.204 no
C(15) C(15)' . 0.71(2) no
C(15) O(5) . 1.29(2) no
C(15)' O(5) . 1.16(2) no
C(15)' O(5)' . 1.43(2) no
O(5) O(5)' . 1.220(10) no
O(5) C(16) . 1.620(10) no
O(5)' C(16) . 1.320(10) no
C(16) C(17) . 1.440(10) no
C(16) H(161) . 1.00 no
C(16) H(162) . 0.948 no
C(17) O(6) . 1.400(9) no
C(17) H(171) . 1.041 no
C(17) H(172) . 0.923 no
O(6) C(18) . 1.590(10) no
O(6) C(18)' . 1.355(8) no
C(18) C(18)' . 1.05(2) no
C(18) C(19) . 1.140(10) no
C(18) H(191) . 1.07 no
C(18)' C(19) . 1.450(10) no
C(19) O(7) . 1.413(6) no
C(19) H(191) . 1.009 no
C(19) H(192) . 1.202 no
O(7) C(20) . 1.396(5) no
C(20) C(21) . 1.503(6) no
C(20) H(201) . 0.769 no
C(20) H(202) . 1.084 no
C(21) H(211) . 1.043 no
C(21) H(212) . 1.160 no
