#------------------------------------------------------------------------------
#$Date: 2019-09-28 06:58:12 +0300 (Sat, 28 Sep 2019) $
#$Revision: 218907 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/17/2021783.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_2021783
loop_
_publ_author_name
'Khalilov, Leonard M.'
'Mescheryakova, Ekaterina S.'
'Bikmukhametov, Kamil Sh.'
'Makhmudiyarova, Nataliya N.'
'Shangaraev, Kamil R.'
'Tulyabaev, Arthur R.'
_publ_section_title
;
How the oxazole fragment influences the conformation of the
tetraoxazocane ring in a cyclohexanespiro-3'-(1,2,4,5,7-tetraoxazocane):
single-crystal X-ray and theoretical study
;
_journal_coeditor_code KU3248
_journal_issue 10
_journal_name_full 'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi 10.1107/S2053229619012592
_journal_volume 75
_journal_year 2019
_chemical_absolute_configuration syn
_chemical_formula_iupac 'C16 H26 N2 O5'
_chemical_formula_moiety 'C16 H26 N2 O5'
_chemical_formula_sum 'C16 H26 N2 O5'
_chemical_formula_weight 326.39
_chemical_name_systematic
(2S,5R)-2-Isopropyl-5-methyl-7-(5-methylisoxazol-3-yl)cyclohexanespiro-3'-(1,2,4,5,7-tetraoxazocane)
_space_group_crystal_system monoclinic
_space_group_IT_number 4
_space_group_name_Hall 'P 2yb'
_space_group_name_H-M_alt 'P 1 21 1'
_symmetry_space_group_name_Hall 'P 2yb'
_symmetry_space_group_name_H-M 'P 1 21 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha 90
_cell_angle_beta 99.241(5)
_cell_angle_gamma 90
_cell_formula_units_Z 2
_cell_length_a 6.4074(4)
_cell_length_b 8.1772(8)
_cell_length_c 16.3291(9)
_cell_measurement_reflns_used 1493
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 26.2870
_cell_measurement_theta_min 2.5130
_cell_volume 844.45(11)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2014)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature 293(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 16.1709
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'Agilent Xcalibur Eos'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0263
_diffrn_reflns_av_unetI/netI 0.0533
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_l_max 20
_diffrn_reflns_limit_l_min -21
_diffrn_reflns_number 5338
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 28.940
_diffrn_reflns_theta_min 2.527
_diffrn_source 'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu 0.095
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.70351
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2014)
;
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.284
_exptl_crystal_description plank
_exptl_crystal_F_000 352.0
_exptl_crystal_size_max 0.75
_exptl_crystal_size_mid 0.23
_exptl_crystal_size_min 0.11
_refine_diff_density_max 0.245
_refine_diff_density_min -0.157
_refine_ls_abs_structure_details
;
Flack x determined using 656 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack 0.5(8)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.029
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 212
_refine_ls_number_reflns 3147
_refine_ls_number_restraints 1
_refine_ls_restrained_S_all 1.029
_refine_ls_R_factor_all 0.0763
_refine_ls_R_factor_gt 0.0557
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0514P)^2^+0.1884P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1176
_refine_ls_wR_factor_ref 0.1284
_reflns_number_gt 2379
_reflns_number_total 3147
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file ku3248sup1.cif
_cod_data_source_block I
_cod_original_cell_volume 844.46(11)
_cod_database_code 2021783
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_hkl_file
;
0 -10 0-421.031 394.995 3
0 -10 -1 533.513 447.079 3
0 -10 1 871.622 519.864 3
0 -10 2 473.224 432.344 3
0 -10 3 370.815 340.809 3
0 -10 4 551.914 463.376 3
0 -10 5 190.367 349.375 3
0 -10 6 277.542 343.893 3
0 -9 0-16.7045 290.342 3
0 -9 -1 2048.42 623.433 3
0 -9 1 3849.46 815.301 3
0 -9 2 72.4299 309.364 3
0 -9 -2 590.044 385.923 3
0 -9 3 3785.97 791.718 3
0 -9 4 456.049 418.469 3
0 -9 5 426.968 351.559 3
0 -9 6 319.933 358.782 3
0 -9 7 405.976 344.991 3
0 -9 8 388.403 344.676 3
0 -9 9 791.443 452.235 3
0 -9 10 18.3690 272.723 3
0 -8 0 2135.91 564.248 3
0 -8 1 3690.03 720.847 3
0 -8 -1 3684.86 732.269 3
0 -8 2 3820.04 729.908 3
0 -8 -2 3613.95 701.975 3
0 -8 3 2891.79 623.652 3
0 -8 4 3385.10 679.784 3
0 -8 5 3580.03 739.178 3
0 -8 6 613.480 378.000 3
0 -8 7 1450.33 503.465 3
0 -8 8 3310.63 718.598 3
0 -8 9 185.792 362.779 3
0 -8 10 905.395 305.942 3
0 -8 11 470.805 346.172 3
0 -8 12-184.754 345.711 3
0 -8 13 1718.60 581.835 3
0 -7 0-221.314 307.773 3
0 -7 1 17603.0 1403.98 3
0 -7 -1 17210.4 1392.20 3
0 -7 -2 7580.17 946.927 3
0 -7 2 7046.15 889.199 3
0 -7 -3 21255.1 1561.69 3
0 -7 3 19718.7 1484.13 3
0 -7 4 11029.6 1130.81 3
0 -7 5 3993.85 688.079 3
0 -7 6 1721.76 477.064 3
0 -7 7 1170.69 338.473 3
0 -7 8 3259.39 673.511 3
0 -7 9 4800.84 856.789 3
0 -7 10 3972.20 778.830 3
0 -7 11 1058.22 463.659 3
0 -7 12 322.033 399.184 3
0 -7 13 972.449 452.605 3
0 -7 14 1728.41 574.233 3
0 -7 15 115.324 337.554 3
0 -6 0 6186.49 773.612 3
0 -6 1 528.169 300.956 3
0 -6 -1 521.134 317.998 3
0 -6 -2 692.304 311.137 3
0 -6 2 552.565 294.938 3
0 -6 -3 1077.18 368.682 3
0 -6 3 795.424 336.125 3
0 -6 4 4848.99 691.129 3
0 -6 5 4355.05 659.950 3
0 -6 6 2975.43 560.434 3
0 -6 7 649.455 329.797 3
0 -6 8 5423.92 798.780 3
0 -6 9 14505.7 1298.91 3
0 -6 10 10063.7 1110.62 3
0 -6 11 1010.14 449.229 3
0 -6 12 3118.46 693.192 3
0 -6 13 1205.42 455.944 3
0 -6 14-52.5309 268.231 3
0 -6 15 560.295 380.194 3
0 -6 16 679.028 456.454 3
0 -5 0-103.646 238.481 3
0 -5 1 9451.23 845.693 3
0 -5 -1 9664.92 863.828 3
0 -5 2 11076.3 910.261 3
0 -5 -2 12398.2 988.334 3
0 -5 3 714.221 309.285 3
0 -5 -3 644.383 277.124 3
0 -5 4 12180.7 975.352 3
0 -5 5 10379.8 938.430 3
0 -5 6 18852.7 1286.76 3
0 -5 7 15953.5 1209.92 3
0 -5 8 30167.7 1719.82 3
0 -5 9 30960.1 1785.84 3
0 -5 10 7264.25 894.817 3
0 -5 11 1708.91 491.126 3
0 -5 12 104.083 230.574 3
0 -5 13 4109.39 755.519 3
0 -5 14 954.982 441.924 3
0 -5 15 721.803 397.480 3
0 -5 16 372.717 359.933 3
0 -5 17 24.4698 313.078 3
0 -4 0 10124.1 769.197 3
0 -4 1 9940.09 770.005 3
0 -4 -1 10381.8 786.428 3
0 -4 -2 4130.82 524.219 3
0 -4 2 4022.09 508.712 3
0 -4 3 3227.46 461.277 3
0 -4 4 12606.7 920.141 3
0 -4 5 30999.6 1469.09 3
0 -4 6 20457.2 1227.56 3
0 -4 7 19860.5 1250.55 3
0 -4 8 36202.8 1741.68 3
0 -4 9 11208.5 1008.75 3
0 -4 10 7507.73 854.202 3
0 -4 11 3374.92 620.889 3
0 -4 12 6466.65 848.718 3
0 -4 13 1694.71 478.140 3
0 -4 14 1981.56 541.039 3
0 -4 15 1698.32 532.211 3
0 -4 16 2.33425 278.817 3
0 -4 17 1286.20 498.778 3
0 -4 18 1045.84 439.927 3
0 -3 0 1.06661 150.343 3
0 -3 1 927.710 234.965 3
0 -3 -1 1001.82 262.812 3
0 -3 2 12842.0 761.247 3
0 -3 -2 12538.2 761.563 3
0 -3 3 3469.68 427.221 3
0 -3 4 723.734 259.752 3
0 -3 5 124499. 2611.62 3
0 -3 -6 58987.6 1644.86 4
0 -3 6 58942.0 1871.60 3
0 -3 7 21623.9 1186.52 3
0 -3 -7 22627.6 1061.08 4
0 -3 -8 33545.7 1357.00 4
0 -3 8 32784.4 1528.39 3
0 -3 -9 22053.8 1138.44 4
0 -3 9 20534.9 1264.27 3
0 -3 10 10851.0 966.263 3
0 -3 -10 10309.5 821.402 4
0 -3 -11 20465.2 1200.84 4
0 -3 11 20620.1 1376.74 3
0 -3 11 20995.7 667.116 1
0 -3 -12 799.558 277.484 4
0 -3 12 919.650 380.605 3
0 -3 12 856.660 128.167 1
0 -3 13 2872.40 595.494 3
0 -3 -13 2119.25 438.730 4
0 -3 14 3810.80 698.577 3
0 -3 -14 3357.69 557.117 4
0 -3 15 5485.12 847.432 3
0 -3 -15 5738.96 760.916 4
0 -3 16 324.487 348.598 3
0 -3 -16-115.721 227.799 4
0 -3 -17 183.955 265.392 4
0 -3 17 571.654 468.157 3
0 -3 18 842.210 458.542 3
0 -3 -18 174.424 282.197 4
0 -3 19 133.048 248.217 3
0 -2 0 307446. 2921.24 3
0 -2 1 108343. 1738.02 3
0 -2 -1 113557. 1816.04 3
0 -2 2 20676.7 819.826 3
0 -2 -3 51976.1 1154.73 4
0 -2 3 52043.5 1354.73 3
0 -2 -4 18245.9 738.174 4
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0 -2 -5 88880.6 1732.75 4
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0 -2 6 92320.0 2182.67 3
0 -2 6 90573.8 1433.02 4
0 -2 7 59542.7 1844.17 3
0 -2 -7 60674.1 1607.93 4
0 -2 7 62305.9 1256.15 4
0 -2 8 25231.4 1271.85 3
0 -2 -8 25599.3 1090.96 4
0 -2 8 26192.9 876.340 4
0 -2 9 9777.54 825.162 3
0 -2 -9 10762.7 742.289 4
0 -2 9 10686.4 425.383 1
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0 -2 10 141.702 60.5464 1
0 -2 10 247.541 240.584 3
0 -2 11 1158.09 353.219 3
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0 -2 11 1327.77 145.511 1
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0 -2 12 5069.41 689.880 3
0 -2 -13 9903.40 855.271 4
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0 -2 14 4631.27 747.268 3
0 -2 -14 4160.16 597.016 4
0 -2 15 2503.57 596.148 3
0 -2 -15 2594.07 477.444 4
0 -2 16 4813.72 805.004 3
0 -2 -16 5418.91 730.548 4
0 -2 17 2395.67 666.272 3
0 -2 -17 2764.96 568.852 4
0 -2 -18-80.1350 224.173 4
0 -2 18 601.984 365.873 3
0 -2 -19 65.7819 226.759 4
0 -2 19 171.994 306.259 3
0 -2 -20-6.77551 246.288 4
0 -1 0 121.064 67.3808 3
0 -1 1 465175. 2692.13 3
0 -1 -1 456444. 2621.56 3
0 -1 2 10908.7 464.847 3
0 -1 -2 11507.1 410.147 4
0 -1 3 197177. 2187.78 3
0 -1 3 200962. 1494.73 4
0 -1 -3 198382. 1878.13 4
0 -1 -4 31588.7 825.536 4
0 -1 4 30531.9 656.584 4
0 -1 4 29831.7 948.160 3
0 -1 5 31951.5 1078.34 3
0 -1 5 31908.2 753.845 4
0 -1 -5 31654.2 903.750 4
0 -1 6 11989.9 363.557 1
0 -1 -6 11917.2 451.207 1
0 -1 6 11181.7 708.842 3
0 -1 6 11244.4 497.950 4
0 -1 -6 11989.5 604.324 4
0 -1 -7 24042.2 684.519 1
0 -1 7 23943.2 523.098 1
0 -1 -7 23577.1 900.342 4
0 -1 7 23040.5 1078.58 3
0 -1 7 22951.2 759.701 4
0 -1 -8 11962.8 687.869 4
0 -1 8 11899.5 377.865 1
0 -1 -8 11317.6 501.045 1
0 -1 8 12018.6 845.738 3
0 -1 9 1304.90 324.009 3
0 -1 -9 1019.58 263.018 4
0 -1 9 1409.23 139.211 1
0 -1 -9 1175.74 184.165 1
0 -1 -10 1735.48 230.576 1
0 -1 10 1404.93 351.224 3
0 -1 -10 1783.16 315.346 4
0 -1 -11 2427.44 376.396 4
0 -1 11 2756.94 505.422 3
0 -1 -12 185.569 180.130 4
0 -1 12 256.247 262.368 3
0 -1 -13 2330.88 407.802 4
0 -1 13 2085.56 477.817 3
0 -1 14 494.056 330.328 3
0 -1 -14 380.768 225.282 4
0 -1 -15 7150.59 757.853 4
0 -1 15 7845.09 977.884 3
0 -1 -16 2441.79 489.625 4
0 -1 16 2574.86 593.801 3
0 -1 17 1847.75 502.076 3
0 -1 -17 2184.15 473.366 4
0 -1 18 1007.93 463.662 3
0 -1 -18 199.848 223.458 4
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0 -1 19 2890.23 743.748 3
0 -1 20 265.712 315.918 3
0 -1 -20 259.320 255.995 4
0 -1 -21-685.360 408.823 4
0 0 2 128513. 899.416 2
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0 0 -2 128318. 901.821 2
0 0 -2 127637. 1009.41 4
0 0 -3 20018.6 492.917 4
0 0 3 20950.4 500.455 4
0 0 -3 21454.7 367.891 1
0 0 3 21381.8 346.481 1
0 0 -3 21260.2 457.353 2
0 0 3 20919.9 445.125 2
0 0 -4 585632. 2282.47 1
0 0 -4 584215. 2751.88 2
0 0 4 568977. 3002.85 4
0 0 4 590190. 2767.15 2
0 0 -5 154422. 1765.33 4
0 0 5 157553. 1766.90 4
0 0 -5 156834. 1340.46 1
0 0 5 159072. 1619.31 2
0 0 -5 158891. 1609.29 2
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0 0 -6 151816. 1720.66 2
0 0 -6 150817. 1449.25 1
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0 0 -6 147786. 1921.52 4
0 0 -7 22647.1 816.605 4
0 0 7 23658.8 734.202 2
0 0 -7 23551.9 632.384 1
0 0 -7 23910.1 745.518 2
0 0 7 23832.4 820.473 4
0 0 -8 52.0970 239.306 4
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0 0 8 1002.81 180.261 2
0 0 -8 894.042 148.038 1
0 0 -9 2771.48 248.455 1
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0 0 9 2600.87 276.674 2
0 0 -9 1975.18 212.779 4
0 0 -10 1485.62 238.277 4
0 0 10 1227.98 216.164 2
0 0 11 1192.74 221.134 2
0 0 -11 1935.20 345.953 4
0 0 -12 446.572 234.976 4
0 0 12 430.134 158.771 2
0 0 12 153.487 237.532 3
0 0 -13 1544.67 343.651 4
0 0 13 2072.60 501.901 3
0 0 13 1442.70 263.810 2
0 0 -14 10255.8 835.780 4
0 0 14 11338.3 1113.71 3
0 0 15 5588.55 834.737 3
0 0 -15 4483.40 578.795 4
0 0 -16 1061.18 319.659 4
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0 0 -17 139.720 219.439 4
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0 0 18 669.663 413.326 3
0 0 -19 257.747 201.990 4
0 0 19 99.3810 339.008 3
0 0 20-153.492 375.592 3
0 0 -20 119.529 208.959 4
0 0 -21-229.536 264.189 4
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0 1 1 461122. 2237.75 4
0 1 1 461188. 2689.56 3
0 1 -2 11693.4 490.265 3
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0 1 3 198972. 1841.84 4
0 1 -3 200267. 2231.81 3
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0 1 -6 11170.1 518.315 4
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0 1 -12-244.117 299.910 4
0 1 12 455.264 190.631 2
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0 1 14 431.339 197.129 2
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0 1 15 7322.96 631.003 2
0 1 -16 2681.96 483.419 4
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0 1 20-7.81846 381.519 3
0 2 0 309614. 2868.14 3
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0 2 2 22132.8 829.755 3
0 2 -2 21748.3 834.377 3
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0 2 3 48876.0 1266.96 3
0 2 3 52491.2 1130.82 4
0 2 -3 52078.8 1366.66 3
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0 2 4 18670.0 724.677 4
0 2 -4 18232.5 545.666 4
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0 2 -5 92167.9 2038.88 3
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0 2 -9 10255.3 600.326 4
0 2 10 109.788 116.681 2
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0 0 0 0.00 0.00 0
TITL KLS-31-4-rep in P2(1)
REM P2(1) (#4 in standard setting)
CELL 0.71073 6.407437 8.177201 16.329124 90.0000 99.2412 90.0000
ZERR 3.00 0.000385 0.000817 0.000886 0.0000 0.0054 0.0000
LATT -1
SYMM -x, y+1/2,-z
SFAC C H N O
UNIT 30.00 42.00 6.00 15.00
TREF
HKLF 4
END
;
_shelx_hkl_checksum 81421
_shelx_res_file
;
TITL KLS-31-4-rep in P21 #4
kls-31-4-rep.res
created by SHELXL-2018/3 at 18:07:08 on 15-Jul-2019
REM reset to P21 #4
CELL 0.71073 6.407437 8.177201 16.329124 90 99.2412 90
ZERR 2 0.000385 0.000817 0.000886 0 0.0054 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H N O
UNIT 30 42 6 15
L.S. 8
PLAN 20
BOND
CONF
fmap 2 53
acta
OMIT 1 0 5
OMIT 1 4 0
OMIT -5 -3 5
OMIT -5 1 7
REM
REM
REM
WGHT 0.051400 0.188400
FVAR 9.65434
O7 4 -0.912617 -0.980940 -0.284273 11.00000 0.03433 0.04321 =
0.03227 0.00181 0.00048 -0.00246
O13 4 -0.573865 -0.868940 -0.245191 11.00000 0.03017 0.04107 =
0.04417 0.00964 0.00495 -0.00161
O8 4 -0.990484 -0.862649 -0.350811 11.00000 0.03912 0.05545 =
0.04130 0.00375 0.00105 0.00675
O12 4 -0.592927 -0.733203 -0.305049 11.00000 0.05397 0.03784 =
0.04847 0.00542 0.01598 -0.00687
O16 4 -0.583353 -1.352523 -0.425859 11.00000 0.05338 0.05000 =
0.05984 -0.01019 -0.00266 -0.00556
C14 1 -0.604247 -1.092059 -0.407515 11.00000 0.03441 0.04940 =
0.03121 -0.00571 0.00809 -0.00687
C1 1 -0.774143 -0.895897 -0.221110 11.00000 0.02403 0.03377 =
0.03632 -0.00310 0.00241 -0.00458
C4 1 -1.038682 -0.900222 -0.090979 11.00000 0.05109 0.05586 =
0.05334 0.00275 0.02301 0.00195
AFIX 23
H4A 2 -0.948458 -0.853095 -0.043452 11.00000 -1.20000
H4B 2 -1.172796 -0.927703 -0.074106 11.00000 -1.20000
AFIX 0
C6 1 -0.728503 -1.017580 -0.147510 11.00000 0.03681 0.03984 =
0.03610 -0.00116 0.00233 0.00083
AFIX 13
H6 2 -0.643455 -0.956015 -0.102574 11.00000 -1.20000
AFIX 0
N10 3 -0.688504 -0.935497 -0.411997 11.00000 0.03441 0.05059 =
0.03932 0.00099 0.00533 -0.00358
C3 1 -1.076188 -0.773782 -0.160153 11.00000 0.03988 0.04962 =
0.03828 -0.00770 0.00445 0.00777
AFIX 13
H3 2 -1.179184 -0.819318 -0.205252 11.00000 -1.20000
AFIX 0
N15 3 -0.719015 -1.215488 -0.439423 11.00000 0.04249 0.05445 =
0.06256 -0.00972 -0.00727 -0.00419
C2 1 -0.871994 -0.741601 -0.194048 11.00000 0.03827 0.03930 =
0.03694 -0.00079 0.00251 0.00064
AFIX 23
H2A 2 -0.901144 -0.667672 -0.240947 11.00000 -1.20000
H2B 2 -0.771694 -0.688321 -0.151564 11.00000 -1.20000
AFIX 0
C11 1 -0.560335 -0.798153 -0.383978 11.00000 0.04983 0.04547 =
0.05314 0.00407 0.02313 -0.00754
AFIX 23
H11A 2 -0.587664 -0.712172 -0.425233 11.00000 -1.20000
H11B 2 -0.413037 -0.829402 -0.380108 11.00000 -1.20000
AFIX 0
C17 1 -0.391533 -1.301587 -0.387991 11.00000 0.03948 0.05882 =
0.03839 0.00108 0.00166 -0.00449
C5 1 -0.937480 -1.053938 -0.116662 11.00000 0.05334 0.04707 =
0.04731 0.00259 0.01894 0.00061
AFIX 23
H5A 2 -1.033720 -1.107423 -0.160436 11.00000 -1.20000
H5B 2 -0.911250 -1.128158 -0.069797 11.00000 -1.20000
AFIX 0
C9 1 -0.912659 -0.915071 -0.423610 11.00000 0.04477 0.06229 =
0.03641 0.00131 0.00255 0.00364
AFIX 23
H9A 2 -0.953409 -0.835479 -0.467299 11.00000 -1.20000
H9B 2 -0.979222 -1.018170 -0.441895 11.00000 -1.20000
AFIX 0
C20 1 -0.595263 -1.169031 -0.160634 11.00000 0.04665 0.03812 =
0.04521 0.00387 0.01011 0.00483
AFIX 13
H20 2 -0.479007 -1.131949 -0.188375 11.00000 -1.20000
AFIX 0
C18 1 -0.395205 -1.141557 -0.375103 11.00000 0.03409 0.05161 =
0.04263 -0.00696 0.00434 -0.00982
AFIX 43
H18 2 -0.284448 -1.075902 -0.350161 11.00000 -1.20000
AFIX 0
C21 1 -0.496707 -1.240349 -0.077195 11.00000 0.08136 0.06851 =
0.06250 0.01365 0.00089 0.02712
AFIX 137
H21A 2 -0.430521 -1.154539 -0.042158 11.00000 -1.50000
H21B 2 -0.392731 -1.320597 -0.085466 11.00000 -1.50000
H21C 2 -0.604739 -1.290871 -0.051358 11.00000 -1.50000
AFIX 0
C23 1 -1.167884 -0.617237 -0.131320 11.00000 0.06724 0.07274 =
0.05572 -0.00292 0.01538 0.01838
AFIX 137
H23A 2 -1.297831 -0.641094 -0.111568 11.00000 -1.50000
H23B 2 -1.194734 -0.541725 -0.176809 11.00000 -1.50000
H23C 2 -1.069202 -0.569678 -0.087307 11.00000 -1.50000
AFIX 0
C19 1 -0.230052 -1.431030 -0.367721 11.00000 0.06408 0.06054 =
0.05681 -0.00316 0.00116 0.00738
AFIX 137
H19A 2 -0.252948 -1.487000 -0.318251 11.00000 -1.50000
H19B 2 -0.091796 -1.382563 -0.358950 11.00000 -1.50000
H19C 2 -0.240672 -1.507487 -0.412814 11.00000 -1.50000
AFIX 0
C22 1 -0.712577 -1.301353 -0.214539 11.00000 0.08337 0.03904 =
0.07132 -0.00409 0.01688 0.00338
AFIX 137
H22A 2 -0.826947 -1.341715 -0.188796 11.00000 -1.50000
H22B 2 -0.617305 -1.389338 -0.220925 11.00000 -1.50000
H22C 2 -0.767770 -1.256802 -0.268034 11.00000 -1.50000
AFIX 0
HKLF 4
REM KLS-31-4-rep in P21 #4
REM wR2 = 0.1284, GooF = S = 1.029, Restrained GooF = 1.029 for all data
REM R1 = 0.0557 for 2379 Fo > 4sig(Fo) and 0.0763 for all 3147 data
REM 212 parameters refined using 1 restraints
END
WGHT 0.0514 0.1854
REM Highest difference peak 0.245, deepest hole -0.157, 1-sigma level 0.042
Q1 1 -0.4122 -0.8798 -0.2415 11.00000 0.05 0.24
Q2 1 -0.9505 -0.7764 -0.1633 11.00000 0.05 0.21
Q3 1 -1.0808 -0.9247 -0.4148 11.00000 0.05 0.20
Q4 1 -0.9533 -0.8847 -0.2264 11.00000 0.05 0.19
Q5 1 -1.0997 -0.9804 -0.2931 11.00000 0.05 0.18
Q6 1 -0.6999 -0.7201 -0.1816 11.00000 0.05 0.17
Q7 1 -0.1709 -1.4156 -0.3209 11.00000 0.05 0.17
Q8 1 -0.7654 -0.7213 -0.3046 11.00000 0.05 0.16
Q9 1 -0.6383 -0.6990 -0.4212 11.00000 0.05 0.16
Q10 1 -1.1406 -0.8643 -0.3442 11.00000 0.05 0.16
Q11 1 -0.9257 -1.1653 -0.4358 11.00000 0.05 0.16
Q12 1 -0.2175 -1.2929 -0.3962 11.00000 0.05 0.16
Q13 1 -0.5350 -0.9146 -0.4203 11.00000 0.05 0.16
Q14 1 -0.4114 -0.7213 -0.3091 11.00000 0.05 0.16
Q15 1 -0.3596 -0.8564 -0.3389 11.00000 0.05 0.16
Q16 1 -1.2464 -0.9012 -0.0967 11.00000 0.05 0.16
Q17 1 -1.0746 -1.0807 -0.3978 11.00000 0.05 0.15
Q18 1 -0.4007 -1.0590 -0.1590 11.00000 0.05 0.15
Q19 1 -0.1979 -0.7256 -0.3226 11.00000 0.05 0.15
Q20 1 -0.0910 -1.3968 -0.3978 11.00000 0.05 0.15
;
_shelx_res_checksum 26845
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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
O O7 -0.9126(4) -0.9809(4) -0.28427(15) 0.0371(7) Uani d 1
O O13 -0.5739(3) -0.8689(4) -0.24519(16) 0.0386(7) Uani d 1
O O8 -0.9905(4) -0.8626(4) -0.35081(16) 0.0459(8) Uani d 1
O O12 -0.5929(4) -0.7332(4) -0.30505(17) 0.0459(7) Uani d 1
O O16 -0.5834(5) -1.3525(4) -0.4259(2) 0.0557(9) Uani d 1
C C14 -0.6042(6) -1.0921(6) -0.4075(2) 0.0380(10) Uani d 1
C C1 -0.7741(5) -0.8959(5) -0.2211(2) 0.0316(9) Uani d 1
C C4 -1.0387(7) -0.9002(7) -0.0910(3) 0.0518(13) Uani d 1
H H4A -0.948458 -0.853095 -0.043452 0.062 Uiso calc 1
H H4B -1.172796 -0.927703 -0.074106 0.062 Uiso calc 1
C C6 -0.7285(6) -1.0176(6) -0.1475(2) 0.0380(10) Uani d 1
H H6 -0.643455 -0.956015 -0.102574 0.046 Uiso calc 1
N N10 -0.6885(5) -0.9355(5) -0.41200(19) 0.0415(9) Uani d 1
C C3 -1.0762(6) -0.7738(6) -0.1602(2) 0.0428(11) Uani d 1
H H3 -1.179184 -0.819318 -0.205252 0.051 Uiso calc 1
N N15 -0.7190(5) -1.2155(6) -0.4394(2) 0.0549(11) Uani d 1
C C2 -0.8720(6) -0.7416(6) -0.1940(2) 0.0386(10) Uani d 1
H H2A -0.901144 -0.667672 -0.240947 0.046 Uiso calc 1
H H2B -0.771694 -0.688321 -0.151564 0.046 Uiso calc 1
C C11 -0.5603(7) -0.7982(6) -0.3840(3) 0.0478(11) Uani d 1
H H11A -0.587664 -0.712172 -0.425233 0.057 Uiso calc 1
H H11B -0.413037 -0.829402 -0.380108 0.057 Uiso calc 1
C C17 -0.3915(6) -1.3016(7) -0.3880(2) 0.0461(12) Uani d 1
C C5 -0.9375(7) -1.0539(6) -0.1167(3) 0.0480(12) Uani d 1
H H5A -1.033720 -1.107423 -0.160436 0.058 Uiso calc 1
H H5B -0.911250 -1.128158 -0.069797 0.058 Uiso calc 1
C C9 -0.9127(6) -0.9151(7) -0.4236(2) 0.0483(12) Uani d 1
H H9A -0.953409 -0.835479 -0.467299 0.058 Uiso calc 1
H H9B -0.979222 -1.018170 -0.441895 0.058 Uiso calc 1
C C20 -0.5953(6) -1.1690(6) -0.1606(3) 0.0430(11) Uani d 1
H H20 -0.479007 -1.131949 -0.188375 0.052 Uiso calc 1
C C18 -0.3952(6) -1.1416(6) -0.3751(2) 0.0430(11) Uani d 1
H H18 -0.284448 -1.075902 -0.350161 0.052 Uiso calc 1
C C21 -0.4967(8) -1.2403(8) -0.0772(3) 0.0720(16) Uani d 1
H H21A -0.430521 -1.154539 -0.042158 0.108 Uiso calc 1
H H21B -0.392731 -1.320597 -0.085466 0.108 Uiso calc 1
H H21C -0.604739 -1.290871 -0.051358 0.108 Uiso calc 1
C C23 -1.1679(8) -0.6172(8) -0.1313(3) 0.0646(15) Uani d 1
H H23A -1.297831 -0.641094 -0.111568 0.097 Uiso calc 1
H H23B -1.194734 -0.541725 -0.176809 0.097 Uiso calc 1
H H23C -1.069202 -0.569678 -0.087307 0.097 Uiso calc 1
C C19 -0.2301(7) -1.4310(7) -0.3677(3) 0.0614(14) Uani d 1
H H19A -0.252948 -1.487000 -0.318251 0.092 Uiso calc 1
H H19B -0.091796 -1.382563 -0.358950 0.092 Uiso calc 1
H H19C -0.240672 -1.507487 -0.412814 0.092 Uiso calc 1
C C22 -0.7126(9) -1.3014(7) -0.2145(3) 0.0641(14) Uani d 1
H H22A -0.826947 -1.341715 -0.188796 0.096 Uiso calc 1
H H22B -0.617305 -1.389338 -0.220925 0.096 Uiso calc 1
H H22C -0.767770 -1.256802 -0.268034 0.096 Uiso calc 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O7 0.0343(13) 0.043(2) 0.0323(13) -0.0025(12) 0.0005(11) 0.0018(13)
O13 0.0302(12) 0.0411(19) 0.0442(14) -0.0016(13) 0.0050(10) 0.0096(14)
O8 0.0391(13) 0.055(2) 0.0413(15) 0.0067(14) 0.0010(11) 0.0038(15)
O12 0.0540(16) 0.038(2) 0.0485(16) -0.0069(15) 0.0160(13) 0.0054(15)
O16 0.0534(17) 0.050(2) 0.0598(18) -0.0056(16) -0.0027(14) -0.0102(17)
C14 0.0344(19) 0.049(3) 0.031(2) -0.007(2) 0.0081(16) -0.006(2)
C1 0.0240(15) 0.034(3) 0.0363(19) -0.0046(16) 0.0024(13) -0.0031(19)
C4 0.051(2) 0.056(4) 0.053(2) 0.002(2) 0.0230(19) 0.003(3)
C6 0.0368(19) 0.040(3) 0.036(2) 0.0008(18) 0.0023(16) -0.001(2)
N10 0.0344(16) 0.051(3) 0.0393(18) -0.0036(17) 0.0053(13) 0.0010(18)
C3 0.040(2) 0.050(3) 0.038(2) 0.008(2) 0.0045(17) -0.008(2)
N15 0.0425(18) 0.054(3) 0.063(2) -0.004(2) -0.0073(17) -0.010(2)
C2 0.0383(19) 0.039(3) 0.0369(19) 0.0006(19) 0.0025(16) -0.0008(19)
C11 0.050(2) 0.045(3) 0.053(2) -0.008(2) 0.023(2) 0.004(2)
C17 0.039(2) 0.059(4) 0.038(2) -0.004(2) 0.0017(18) 0.001(2)
C5 0.053(2) 0.047(3) 0.047(2) 0.001(2) 0.019(2) 0.003(2)
C9 0.045(2) 0.062(4) 0.036(2) 0.004(2) 0.0026(17) 0.001(2)
C20 0.047(2) 0.038(3) 0.045(2) 0.0048(19) 0.0101(18) 0.004(2)
C18 0.034(2) 0.052(3) 0.043(2) -0.010(2) 0.0043(17) -0.007(2)
C21 0.081(3) 0.069(4) 0.063(3) 0.027(3) 0.001(3) 0.014(3)
C23 0.067(3) 0.073(4) 0.056(3) 0.018(3) 0.015(2) -0.003(3)
C19 0.064(3) 0.061(4) 0.057(3) 0.007(3) 0.001(2) -0.003(3)
C22 0.083(3) 0.039(3) 0.071(3) 0.003(3) 0.017(3) -0.004(3)
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
C1 O7 O8 108.0(3)
C1 O13 O12 108.6(2)
C9 O8 O7 107.1(3)
C11 O12 O13 107.9(3)
C17 O16 N15 108.6(4)
N10 C14 C18 128.3(4)
N15 C14 N10 120.2(4)
N15 C14 C18 111.4(4)
O7 C1 C6 105.4(3)
O7 C1 C2 112.3(3)
O13 C1 O7 111.1(3)
O13 C1 C6 104.4(3)
O13 C1 C2 112.9(3)
C2 C1 C6 110.2(3)
H4A C4 H4B 107.8
C3 C4 H4A 109.1
C3 C4 H4B 109.1
C5 C4 H4A 109.1
C5 C4 H4B 109.1
C5 C4 C3 112.6(3)
C1 C6 H6 105.3
C5 C6 C1 108.2(3)
C5 C6 H6 105.3
C5 C6 C20 115.0(4)
C20 C6 C1 116.6(3)
C20 C6 H6 105.3
C14 N10 C11 120.8(3)
C14 N10 C9 119.3(4)
C11 N10 C9 117.8(4)
C4 C3 H3 107.9
C4 C3 C2 110.2(3)
C2 C3 H3 107.9
C23 C3 C4 111.5(4)
C23 C3 H3 107.9
C23 C3 C2 111.4(4)
C14 N15 O16 104.9(3)
C1 C2 C3 112.6(4)
C1 C2 H2A 109.1
C1 C2 H2B 109.1
C3 C2 H2A 109.1
C3 C2 H2B 109.1
H2A C2 H2B 107.8
O12 C11 H11A 108.6
O12 C11 H11B 108.6
N10 C11 O12 114.8(3)
N10 C11 H11A 108.6
N10 C11 H11B 108.6
H11A C11 H11B 107.5
O16 C17 C19 115.7(5)
C18 C17 O16 109.8(4)
C18 C17 C19 134.4(4)
C4 C5 C6 111.6(4)
C4 C5 H5A 109.3
C4 C5 H5B 109.3
C6 C5 H5A 109.3
C6 C5 H5B 109.3
H5A C5 H5B 108.0
O8 C9 N10 113.8(3)
O8 C9 H9A 108.8
O8 C9 H9B 108.8
N10 C9 H9A 108.8
N10 C9 H9B 108.8
H9A C9 H9B 107.7
C6 C20 H20 107.2
C21 C20 C6 110.1(4)
C21 C20 H20 107.2
C22 C20 C6 114.9(4)
C22 C20 H20 107.2
C22 C20 C21 110.0(4)
C14 C18 H18 127.4
C17 C18 C14 105.2(4)
C17 C18 H18 127.4
C20 C21 H21A 109.5
C20 C21 H21B 109.5
C20 C21 H21C 109.5
H21A C21 H21B 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C3 C23 H23A 109.5
C3 C23 H23B 109.5
C3 C23 H23C 109.5
H23A C23 H23B 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
C17 C19 H19A 109.5
C17 C19 H19B 109.5
C17 C19 H19C 109.5
H19A C19 H19B 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C20 C22 H22A 109.5
C20 C22 H22B 109.5
C20 C22 H22C 109.5
H22A C22 H22B 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O7 O8 1.480(4)
O7 C1 1.429(4)
O13 O12 1.471(4)
O13 C1 1.418(4)
O8 C9 1.427(5)
O12 C11 1.440(5)
O16 N15 1.414(5)
O16 C17 1.350(5)
C14 N10 1.387(6)
C14 N15 1.307(6)
C14 C18 1.418(6)
C1 C6 1.551(5)
C1 C2 1.506(6)
C4 H4A 0.9700
C4 H4B 0.9700
C4 C3 1.522(6)
C4 C5 1.505(7)
C6 H6 0.9800
C6 C5 1.534(5)
C6 C20 1.539(6)
N10 C11 1.423(6)
N10 C9 1.428(5)
C3 H3 0.9800
C3 C2 1.523(5)
C3 C23 1.515(7)
C2 H2A 0.9700
C2 H2B 0.9700
C11 H11A 0.9700
C11 H11B 0.9700
C17 C18 1.326(7)
C17 C19 1.480(7)
C5 H5A 0.9700
C5 H5B 0.9700
C9 H9A 0.9700
C9 H9B 0.9700
C20 H20 0.9800
C20 C21 1.523(6)
C20 C22 1.516(7)
C18 H18 0.9300
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
C23 H23A 0.9600
C23 H23B 0.9600
C23 H23C 0.9600
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
C22 H22A 0.9600
C22 H22B 0.9600
C22 H22C 0.9600
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O7 O8 C9 N10 -54.7(5)
O7 C1 C6 C5 -63.1(4)
O7 C1 C6 C20 68.4(4)
O7 C1 C2 C3 59.2(4)
O13 O12 C11 N10 52.2(4)
O13 C1 C6 C5 179.7(3)
O13 C1 C6 C20 -48.7(4)
O13 C1 C2 C3 -174.3(3)
O8 O7 C1 O13 -76.8(3)
O8 O7 C1 C6 170.8(2)
O8 O7 C1 C2 50.8(4)
O12 O13 C1 O7 76.7(4)
O12 O13 C1 C6 -170.2(3)
O12 O13 C1 C2 -50.5(4)
O16 C17 C18 C14 0.0(5)
C14 N10 C11 O12 -104.1(4)
C14 N10 C9 O8 106.1(5)
C1 O7 O8 C9 115.9(3)
C1 O13 O12 C11 -113.5(3)
C1 C6 C5 C4 -57.8(5)
C1 C6 C20 C21 159.1(4)
C1 C6 C20 C22 -76.1(5)
C4 C3 C2 C1 54.2(4)
C6 C1 C2 C3 -58.0(4)
N10 C14 N15 O16 178.4(3)
N10 C14 C18 C17 -177.6(4)
C3 C4 C5 C6 56.4(5)
N15 O16 C17 C18 0.9(5)
N15 O16 C17 C19 179.0(4)
N15 C14 N10 C11 -174.6(4)
N15 C14 N10 C9 22.1(6)
N15 C14 C18 C17 -1.0(5)
C2 C1 C6 C5 58.3(4)
C2 C1 C6 C20 -170.2(3)
C11 N10 C9 O8 -57.7(6)
C17 O16 N15 C14 -1.5(4)
C5 C4 C3 C2 -52.9(5)
C5 C4 C3 C23 -177.1(4)
C5 C6 C20 C21 -72.6(5)
C5 C6 C20 C22 52.2(5)
C9 N10 C11 O12 59.5(5)
C20 C6 C5 C4 169.8(3)
C18 C14 N10 C11 1.8(6)
C18 C14 N10 C9 -161.6(4)
C18 C14 N15 O16 1.5(5)
C23 C3 C2 C1 178.5(3)
C19 C17 C18 C14 -177.5(5)
_cod_database_fobs_code 2021783