#------------------------------------------------------------------------------
#$Date: 2024-03-29 05:06:37 +0200 (Fri, 29 Mar 2024) $
#$Revision: 290711 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/30/2023077.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_2023077
loop_
_publ_author_name
'Businski, Artjom'
'Ta, Thuy C.'
'Gindullis, Niklas'
'N\"ather, Christian'
'Herges, Rainer'
_publ_section_title
;
Synthesis and crystal structure of tetramethyl
(E)-4,4′-(ethene-1,2-diyl)bis(5-nitrobenzene-1,2-dicarboxylate)
;
_journal_coeditor_code WM5712
_journal_issue 4
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_page_first 435
_journal_page_last 438
_journal_paper_doi 10.1107/S2056989024002676
_journal_volume 80
_journal_year 2024
_chemical_formula_iupac 'C22 H18 N2 O12'
_chemical_formula_moiety 'C22 H18 N2 O12'
_chemical_formula_sum 'C22 H18 N2 O12'
_chemical_formula_weight 502.38
_chemical_name_systematic
;
Tetramethyl
(E)-4,4'-(ethene-1,2-diyl)bis(5-nitrobenzene-1,2-dicarboxylate)
;
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_Hall '-P 1'
_space_group_name_H-M_alt 'P -1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_cell_angle_alpha 72.124(3)
_cell_angle_beta 79.661(3)
_cell_angle_gamma 86.052(3)
_cell_formula_units_Z 1
_cell_length_a 5.9454(2)
_cell_length_b 7.9543(3)
_cell_length_c 12.0673(4)
_cell_measurement_reflns_used 3255
_cell_measurement_temperature 100.00(10)
_cell_measurement_theta_max 78.7870
_cell_measurement_theta_min 3.8830
_cell_volume 534.25(3)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2022)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2022)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2022)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg & Putz, 1999) and XP in SHELXTL-PC
(Sheldrick, 2008)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature 100.00(10)
_diffrn_detector 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_monochromator mirror
_diffrn_radiation_probe x-ray
_diffrn_radiation_type 'Cu K\a'
_diffrn_radiation_wavelength 1.54184
_diffrn_reflns_av_R_equivalents 0.0204
_diffrn_reflns_av_unetI/netI 0.0255
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_k_max 6
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_number 5274
_diffrn_reflns_theta_full 67.684
_diffrn_reflns_theta_max 80.114
_diffrn_reflns_theta_min 3.904
_diffrn_source 'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu 1.120
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.79073
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2022)
;
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.561
_exptl_crystal_description plate
_exptl_crystal_F_000 260
_exptl_crystal_size_max 0.19
_exptl_crystal_size_mid 0.08
_exptl_crystal_size_min 0.02
_refine_diff_density_max 0.371
_refine_diff_density_min -0.301
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.087
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 165
_refine_ls_number_reflns 2211
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.087
_refine_ls_R_factor_all 0.0458
_refine_ls_R_factor_gt 0.0429
_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^)+(0.0710P)^2^+0.2093P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1224
_refine_ls_wR_factor_ref 0.1247
_reflns_number_gt 2042
_reflns_number_total 2211
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file wm5712.cif
_cod_data_source_block I
_cod_database_code 2023077
_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 0 1 43677.2 1146.58 11
0 0 2 13287.0 367.173 11
0 0 3 101135. 2664.71 11
0 0 4 6230.37 211.387 11
0 0 5 125448. 3328.51 11
0 0 -6 273.638 75.1082 18
0 0 7 41.5203 37.6209 23
0 0 -7 72.8090 74.2277 18
0 0 8 28502.5 775.341 23
0 0 -8 29149.6 891.235 18
0 0 9 871.037 66.1748 23
0 0 -9 701.541 121.017 12
0 0 -9 785.498 129.508 18
0 0 10 841.417 71.0860 23
0 0 -10 680.257 133.117 18
0 0 11 182.605 56.4169 23
0 0 12 4956.74 167.306 23
0 0 13 296.733 51.2021 27
0 0 14 231.763 34.9619 27
0 0 14 164.783 39.2057 35
0 -1 13 15752.8 426.505 43
0 -1 13 16254.8 425.038 27
0 -1 12 5443.91 175.942 27
0 -1 11 594.691 65.8714 44
0 -1 11 419.157 60.7381 23
0 -1 10 631.748 70.4167 44
0 1 -10 521.422 72.2774 34
0 -1 10 658.823 65.0135 23
0 1 -9 9927.91 300.133 34
0 -1 9 10365.0 300.017 23
0 1 -9 8535.44 400.683 12
0 -1 9 10198.7 301.702 44
0 1 -9 8933.35 404.098 18
0 1 -8 105.101 89.7678 18
0 -1 8 92.0588 46.3019 23
0 1 -7 20486.8 658.011 18
0 -1 7 20586.6 563.331 23
0 -1 6 11277.3 316.178 23
0 -1 5 3884.23 180.792 11
0 -1 4 14184.8 433.663 11
0 -1 3 20431.0 581.202 11
0 -1 2 14607.1 399.521 4
0 -1 2 15019.7 400.911 3
0 -1 2 13654.7 415.005 11
0 -1 1 69566.6 1816.45 4
0 -1 1 66851.8 1817.21 2
0 -1 1 69626.9 1822.82 13
0 -1 1 70386.5 1818.03 3
0 -1 0 30130.0 165.919 11
0 -1 0 30654.9 121.775 15
0 -1 -1 2627.39 91.7655 4
0 -1 -1 2817.69 92.5760 12
0 -1 -1 2889.55 87.0473 14
0 -1 -1 3071.91 96.2242 18
0 -1 -2 71960.4 1890.40 4
0 -1 -2 74012.2 1897.52 12
0 -1 -2 73482.8 1892.41 2
0 1 2 70651.4 1879.64 11
0 -1 -2 72097.6 1891.08 3
0 -1 -3 228866. 6052.09 4
0 -1 -3 230845. 6052.07 3
0 1 3 235479. 6051.35 11
0 1 4 17372.5 486.330 11
0 -1 -5 56971.7 1559.54 18
0 -1 -6 1679.73 126.402 18
0 -1 -7 3535.60 190.815 18
0 1 7 3219.92 109.610 23
0 -1 -8 22545.4 702.067 18
0 1 8 21183.7 584.497 23
0 1 9 8601.30 255.892 23
0 -1 -9 7841.53 363.430 18
0 1 10 1470.29 85.5821 44
0 -1 -10 1373.34 162.474 18
0 -1 -10 1410.89 87.2727 34
0 1 10 1539.66 84.5071 23
0 1 11 8916.78 268.892 44
0 -1 -11 8350.01 267.507 34
0 -1 -11 8388.40 260.819 25
0 1 11 8918.61 267.114 23
0 1 12 1548.74 85.2137 23
0 1 12 1638.38 89.9667 44
0 1 13 2268.44 98.4216 44
0 1 13 2450.95 100.361 27
0 1 14 407.512 44.9955 27
0 -2 13 2777.72 87.1958 35
0 -2 12 3802.17 136.995 35
0 -2 12 3990.53 129.115 43
0 -2 11 307.664 54.6320 27
0 -2 10 22569.9 616.022 27
0 -2 10 21937.6 616.027 23
0 2 -9 260.217 63.3208 34
0 -2 9 237.001 62.2148 44
0 -2 9 237.775 53.4427 23
0 -2 8 5418.67 170.497 23
0 -2 8 4899.43 171.907 44
0 2 -8 4952.58 171.474 34
0 -2 7 3394.18 119.999 22
0 -2 7 3350.36 120.629 23
0 -2 6 10254.2 288.846 23
0 -2 6 10353.3 288.892 22
0 -2 5 8978.07 313.652 13
0 -2 4 65800.0 1784.63 13
0 -2 3 32914.0 908.495 4
0 -2 3 33834.1 927.980 13
0 -2 2 471.989 68.4391 13
0 -2 2 372.881 75.7673 11
0 -2 2 471.588 58.2679 4
0 -2 2 490.517 56.5757 3
0 -2 1 111318. 3053.54 11
0 -2 1 119729. 3058.03 3
0 -2 1 115717. 3060.82 13
0 -2 1 117002. 3054.71 4
0 -2 0 169075. 4437.57 3
0 -2 0 169941. 4440.03 13
0 -2 0 168816. 4438.16 2
0 -2 0 168352. 4425.43 11
0 -2 -1 35069.4 955.231 2
0 -2 -1 35196.1 945.163 16
0 -2 -2 5772.47 170.564 14
0 -2 -2 5629.02 190.046 2
0 -2 -2 5440.44 186.500 3
0 -2 -2 5803.30 184.148 12
0 -2 -2 5433.89 186.594 4
0 -2 -3 240127. 6302.84 4
0 -2 -3 243613. 6309.72 18
0 -2 -3 237329. 6302.97 3
0 -2 -3 242012. 6305.75 12
0 -2 -4 328360. 8598.35 18
0 -2 -4 325030. 8596.02 12
0 -2 -4 326419. 8579.75 3
0 -2 -4 331433. 8579.68 4
0 -2 -5 9913.78 331.251 12
0 -2 -5 9855.30 334.930 18
0 -2 -5 9748.63 298.118 4
0 -2 -6 22696.5 688.985 12
0 -2 -6 23321.6 699.912 18
0 -2 -7 49447.7 1404.71 12
0 -2 -8 1240.36 133.530 12
0 2 8 1337.28 66.3455 23
0 -2 -9 50506.0 1484.47 12
0 2 9 50494.3 1345.58 23
0 -2 -10 6787.53 215.433 34
0 2 10 6730.28 213.303 23
0 -2 -10 6437.47 334.574 12
0 2 11 14962.3 420.100 23
0 -2 -11 14703.9 421.587 25
0 2 11 14224.8 419.542 44
0 2 12 9048.88 269.201 44
0 -2 -12 8785.46 265.325 25
0 2 12 8516.90 264.956 23
0 2 13 276.094 52.3723 44
0 -2 -13 188.767 42.6869 25
0 2 14 22.2163 43.4261 27
0 2 15 476.413 31.0255 27
0 -3 12 597.057 43.5795 35
0 -3 11 3439.49 127.534 35
0 -3 10 414.735 69.5645 35
0 -3 10 482.783 56.8219 43
0 -3 9 1586.57 84.0381 27
0 -3 8 1745.24 89.4348 27
0 -3 8 1920.10 88.5070 23
0 3 -8 1706.90 92.3405 34
0 -3 7 7604.98 224.969 23
0 3 -7 7003.19 226.116 34
0 -3 6 2747.89 105.929 23
0 -3 6 3070.81 112.653 22
0 -3 5-8.42572 61.3396 13
0 -3 5 70.7148 43.5510 22
0 -3 5 26.0104 36.8738 23
0 -3 4 77201.0 2103.74 13
0 -3 4 77134.4 2031.54 22
0 -3 3 14529.3 452.838 4
0 -3 3 15284.2 471.168 13
0 -3 2 36453.4 997.105 4
0 -3 2 34754.0 1005.19 13
0 -3 1 976.963 91.1833 13
0 -3 1 1185.50 90.9166 3
0 -3 1 1077.38 88.7146 4
0 -3 0 42438.4 1177.94 17
0 -3 0 42061.1 1173.11 4
0 -3 0 43466.6 1177.81 3
0 -3 -1 11447.2 365.090 3
0 -3 -1 11839.6 367.723 17
0 -3 -2 21087.8 630.260 4
0 -3 -2 22564.8 621.557 16
0 -3 -3 163743. 4318.06 3
0 -3 -3 161574. 4320.58 17
0 -3 -3 163013. 4301.39 12
0 -3 -3 165507. 4311.60 16
0 -3 -3 162596. 4315.50 4
0 -3 -4 6478.45 226.219 3
0 -3 -4 6301.71 226.190 4
0 -3 -4 5794.30 200.236 14
0 -3 -4 6050.11 221.373 12
0 -3 -5 7389.51 271.656 18
0 -3 -5 6888.50 253.185 12
0 -3 -5 7109.05 247.266 4
0 -3 -6 562.935 97.3145 18
0 -3 -6 470.084 85.2223 12
0 -3 -6 546.043 73.4311 4
0 -3 -7 9466.74 360.451 18
0 -3 -7 8877.96 344.942 12
0 -3 -8 169.954 87.8877 12
0 -3 -8 121.075 100.347 18
0 -3 -9 12202.5 351.960 25
0 -3 -9 12564.7 488.371 18
0 -3 -9 12074.1 463.117 12
0 3 9 11653.8 339.667 23
0 -3 -10 445.356 61.9108 25
0 3 10 376.770 54.5336 23
0 -3 -10 452.964 119.833 12
0 -3 -10 265.328 57.0391 45
0 -3 -10 181.074 118.438 18
0 3 11 11381.4 329.914 44
0 3 11 11069.8 327.032 23
0 -3 -11 10437.8 333.343 56
0 3 12 6932.12 221.250 44
0 -3 -12 7328.10 227.280 25
0 -3 -13 1305.20 71.0083 25
0 3 13 1155.35 69.4893 44
0 3 14 1237.83 65.0186 27
0 -4 11 83.4326 34.3366 35
0 -4 10 3279.60 122.673 35
0 -4 9 2267.56 110.312 35
0 -4 8 285.167 73.6814 35
0 -4 7 2364.83 130.743 35
0 -4 6 4416.69 181.224 35
0 -4 5 2457.39 105.622 22
0 -4 4 78.3761 45.2981 22
0 -4 4 95.2774 69.3706 17
0 -4 4-19.0287 65.6091 13
0 -4 3 10264.0 362.966 4
0 -4 3 10100.0 371.465 17
0 -4 3 10638.6 375.592 13
0 -4 2 13562.0 443.635 17
0 -4 2 13861.8 437.079 4
0 -4 2 12637.7 361.188 22
0 -4 1 189.484 71.5313 17
0 -4 1 124.418 69.2344 4
0 -4 0 24463.4 723.104 4
0 -4 0 23830.9 723.331 17
0 -4 0 24080.5 728.458 3
0 -4 -1 199.421 69.8346 17
0 -4 -1 290.296 70.6890 3
0 -4 -2 2122.72 132.445 4
0 -4 -2 1952.48 127.052 17
0 -4 -3 1160.82 102.910 3
0 -4 -3 1032.07 102.249 4
0 -4 -3 1137.82 92.7890 16
0 -4 -4 98171.2 2676.08 16
0 -4 -4 101066. 2690.62 4
0 -4 -5 15998.8 507.244 4
0 -4 -5 15792.6 508.229 16
0 -4 -5 15194.8 488.417 12
0 -4 -6 21098.6 578.069 25
0 -4 -6 21067.6 670.706 16
0 -4 -6 20853.0 646.039 4
0 -4 -6 21058.4 647.555 12
0 -4 -7 43187.1 1251.34 12
0 -4 -7 44240.3 1280.03 16
0 -4 -7 43309.1 1164.45 25
0 -4 -8 23910.4 760.378 12
0 -4 -9 11479.0 349.265 45
0 -4 -9 12544.2 355.373 25
0 -4 -9 11248.0 453.576 12
0 -4 -10 4691.27 306.701 16
0 -4 -10 5867.18 195.106 25
0 -4 -11 17743.5 501.646 25
0 -4 -11 17255.2 502.300 56
0 -4 -12 22625.3 607.135 25
0 -4 -12 21659.5 606.182 56
0 4 12 21098.6 592.195 44
0 4 13 157.169 44.6491 27
0 -4 -13 99.4505 39.8881 56
0 4 13 81.6028 41.6954 44
0 -4 -13 116.984 45.4998 25
0 -4 -14 6411.27 188.740 50
0 -4 -15 1741.52 58.9879 36
0 -5 10 165.201 30.4661 35
0 -5 9 920.681 61.7747 35
0 -5 8 642.765 66.0722 35
0 -5 7 25223.3 708.737 35
0 -5 6 1261.99 99.0074 35
0 -5 6 1151.31 73.1275 33
0 -5 5 8326.63 258.618 33
0 -5 5 8319.91 282.794 35
0 -5 4 61.1313 64.2492 35
0 -5 4 28.1172 48.6051 33
0 -5 3 3755.26 215.207 17
0 -5 3 3953.19 141.883 22
0 -5 2 3866.13 216.934 17
0 -5 2 3881.17 213.620 4
0 -5 2 4054.40 139.810 22
0 -5 1 34865.4 1000.75 17
0 -5 1 32113.4 885.248 22
0 -5 1 35539.3 997.609 4
0 -5 0 6411.80 195.391 22
0 -5 0 6625.22 285.255 17
0 -5 0 6741.58 286.545 4
0 -5 -1 238.771 89.5531 4
0 -5 -1 170.704 79.4643 17
0 -5 -2 7814.73 317.802 17
0 -5 -3 164.454 79.6537 4
0 -5 -4 2200.19 159.614 4
0 -5 -5 2834.91 182.794 4
0 -5 -5 2683.16 165.673 16
0 -5 -5 2974.86 110.916 25
0 -5 -6 7786.12 329.695 16
0 -5 -6 8793.40 341.364 4
0 -5 -6 8259.03 251.444 25
0 -5 -7 1008.17 70.2782 25
0 -5 -7 1025.08 127.984 16
0 -5 -8 62.7740 49.1653 25
0 -5 -8 71.2236 50.7916 26
0 -5 -8 62.4119 89.9681 16
0 -5 -8 23.3984 52.0159 45
0 -5 -9 841.791 74.3997 26
0 -5 -9 804.693 137.274 16
0 -5 -9 1058.15 74.4721 25
0 -5 -10 5887.18 199.063 56
0 -5 -10 5320.30 193.148 31
0 -5 -11 1292.55 77.4633 31
0 -5 -11 1265.29 83.4743 56
0 -5 -11 1300.00 83.3817 25
0 -5 -12 340.900 56.8507 25
0 -5 -12 169.152 50.5885 56
0 -5 -13 93.4504 40.5748 56
0 -5 -14 23567.8 632.355 50
0 -6 8 1119.38 56.8281 48
0 -6 8 1141.82 59.8275 35
0 -6 7 201.537 50.2703 35
0 -6 6 221.025 60.6585 35
0 -6 5 47.1919 61.9386 35
0 -6 5 133.458 46.9329 33
0 -6 4 388.745 57.8594 33
0 -6 4 348.359 70.7523 35
0 -6 4 367.462 59.0209 42
0 -6 3 47.3332 62.4595 35
0 -6 3 55.7500 54.8674 42
0 -6 3-12.4883 52.1865 33
0 -6 2 3965.64 148.098 42
0 -6 2 3322.00 137.382 7
0 -6 2 3755.74 156.581 35
0 -6 2 3194.88 219.227 17
0 -6 2 4009.36 150.458 33
0 -6 1 7924.92 242.426 33
0 -6 1 6513.66 326.727 17
0 -6 1 6963.13 233.002 7
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0 -6 1 7215.89 244.438 35
0 -6 0 10253.5 419.996 17
0 -6 0 10331.8 419.753 4
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0 -6 -1 56165.9 1606.15 4
0 -6 -3 13659.2 510.574 4
0 -6 -4 552.926 116.393 4
0 -6 -5 22090.4 740.738 4
0 -6 -6 913.736 137.804 4
0 -6 -6 1134.74 76.0015 56
0 -6 -6 926.348 74.3297 28
0 -6 -6 1030.10 67.8422 54
0 -6 -6 1133.93 73.3388 7
0 -6 -7 2561.12 111.548 54
0 -6 -7 2863.40 121.873 56
0 -6 -7 2849.59 123.192 26
0 -6 -8 757.047 74.7662 26
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0 -6 -8 916.776 75.9850 56
0 -6 -8 944.995 75.1002 31
0 -6 -9-15.4200 54.8817 26
0 -6 -9 4.18186 53.4186 31
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0 -6 -10 1300.32 82.6307 31
0 -6 -10 1328.78 86.0065 56
0 -6 -11 5903.71 199.385 31
0 -6 -11 6267.31 206.419 56
0 -6 -12 25.5638 43.8654 56
0 -6 -12 48.1255 37.8061 31
0 -6 -12 55.7468 47.7404 50
0 -6 -13 3934.21 134.215 56
0 -6 -13 4158.60 138.071 36
0 -6 -13 3960.41 136.172 50
0 -6 -14 3476.54 99.6711 36
0 -6 -14 2720.53 94.2569 50
0 -7 7 1230.38 49.1875 51
0 -7 7 1105.91 48.0197 35
0 -7 6 933.406 59.5319 48
0 -7 6 801.347 55.3626 51
0 -7 6 793.981 55.2501 35
0 -7 5 754.858 63.4499 51
0 -7 5 860.279 65.0158 48
0 -7 5 806.955 62.9774 35
0 -7 4 3629.78 139.395 51
0 -7 4 3295.79 124.348 33
0 -7 4 3626.40 136.581 35
0 -7 3 3234.13 134.473 51
0 -7 3 3371.89 135.840 35
0 -7 3 3068.44 124.885 33
0 -7 3 3209.65 126.182 42
0 -7 2 3024.51 139.111 51
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-7 1 2 209.538 36.8811 29
7 -1 -1 739.291 38.8129 10
7 -1 -1 698.966 37.3156 8
7 -1 0-0.61296 24.4399 30
-7 1 0 72.0048 40.1815 29
7 -1 0 24.5189 25.5618 8
7 -1 1 80.6859 31.0165 6
7 -1 1 16.2283 27.4092 30
-7 1 -1 33.4695 44.3469 29
7 -1 1 36.1680 28.5224 24
-7 1 -2 6192.17 171.524 29
7 -1 2 5695.39 174.475 8
7 -1 2 5634.12 174.753 6
7 -1 3 474.442 36.4937 30
-7 1 -3 481.059 49.0081 29
7 -1 3 429.196 36.6968 8
7 -1 3 433.556 34.1088 24
7 -1 3 375.248 34.5594 6
7 -1 4 9.03648 25.3440 30
-7 1 -4 5.04579 37.6598 29
7 -1 4 21.2635 26.4041 8
7 -1 5 235.452 24.5296 10
7 -1 5 255.958 28.5392 30
7 -1 5 247.497 24.5670 8
7 -1 6 902.003 36.6296 30
-7 0 1 82.3513 37.1546 29
-7 0 0 420.324 45.7355 29
7 0 0 315.469 32.8265 8
-7 0 -1 207.397 45.6689 29
-7 0 -2 8684.21 242.478 29
7 0 2 8471.23 237.510 55
-7 0 -3 1089.95 58.9901 29
7 0 4 1406.64 62.1892 30
-7 0 -4 1669.83 67.3958 29
7 0 5 391.408 33.8939 30
-7 0 -5 469.868 45.1367 29
7 0 5 348.415 34.0329 8
7 0 6 2280.84 78.5512 10
7 0 6 2349.83 78.9443 8
-7 0 -7 745.518 35.1873 45
-7 -1 2 1924.17 65.5198 29
-7 -1 1 115.640 34.9590 29
7 1 0 50.0614 26.2832 55
7 1 1 1335.64 54.8625 55
7 1 2 680.422 42.3177 55
-7 -1 -3 821.783 55.2378 29
7 1 3 842.014 45.4262 55
-7 -1 -4 150.115 43.7371 29
7 1 4 178.597 33.4020 55
7 1 5 72.4098 30.6164 30
-7 -1 -5 66.9545 39.9189 29
7 1 6 42.3063 25.2652 30
-7 -1 -6 51.7256 36.1339 29
-7 -1 -7 344.367 39.2801 29
-7 -1 -7 308.820 27.9454 45
7 2 -1 13081.7 349.660 55
-7 -2 0 219.005 35.8280 29
7 2 0 257.834 27.8405 55
-7 -2 -1 43.3392 38.0276 29
7 2 1 81.2877 27.9961 55
-7 -2 -2 92.7882 40.3874 29
-7 -2 -3 248.411 42.6771 29
7 2 4 679.070 41.4536 55
7 2 6 1257.81 47.9833 30
-7 -2 -7 88.9174 32.6512 29
-7 -2 -7 86.1806 21.6993 45
-7 -2 -8 3294.06 94.8929 45
7 3 1 259.185 27.0994 55
-7 -3 -2 4501.85 149.631 9
7 3 2 5487.31 145.997 55
7 3 3 3084.87 95.5477 55
-7 -3 -4 1099.92 51.1809 29
7 3 4 1072.27 46.5029 55
-7 -3 -5 377.034 35.3040 9
-7 -3 -5 432.616 38.7483 29
-7 -3 -6 152.458 28.0052 9
-7 -3 -6 201.691 33.0040 29
7 4 2 135.184 19.9872 55
-7 -4 -3 108.397 22.1481 9
7 4 3 152.083 23.8870 55
7 4 4 703.359 33.5495 55
-7 -4 -5 209.698 26.6459 9
-7 -4 -6 11.0501 18.2582 9
0 0 0 0.00 0.00 0
TITL Herges176_auto in P-1
REM P-1 (#2 in standard setting)
CELL 1.54184 5.945394 7.954262 12.067305 72.1244 79.6615 86.0523
ZERR 1.00 0.000224 0.000256 0.000422 0.0031 0.0032 0.0028
LATT 1
SFAC C H N O
UNIT 22.00 18.00 2.00 12.00
REM CrysAlisPro recorded range (K): Min=100.0; max=100.1; aver:100.0
TEMP -173
TREF
HKLF 4
END
;
_shelx_hkl_checksum 17098
_shelx_res_file
;
TITL herges176_a.res in P-1
herges176.res
created by SHELXL-2016/6 at 19:04:49 on 02-Feb-2024
REM Old TITL Herges176_auto in P-1
REM SHELXT solution in P-1
REM R1 0.113, Rweak 0.006, Alpha 0.076, Orientation as input
REM Formula found by SHELXT: C11 N O6
CELL 1.54184 5.945394 7.954262 12.067305 72.1244 79.6615 86.0523
ZERR 1 0.000224 0.000256 0.000422 0.0031 0.0032 0.0028
LATT 1
SFAC C H N O
UNIT 22 18 2 12
EQIV $1 1-X,-Y,2-Z
EQIV $2 +X,-1+Y,+Z
EQIV $3 1+X,+Y,+Z
L.S. 10
PLAN 5
TEMP -173
HTAB C9 O5_$1
HTAB C11 O3_$2
HTAB C11 O5_$3
MPLA C2 C3 C4 C5 C6
MPLA N1 O1 O2
MPLA C8 O3 O4
MPLA C10 O5 O6
BOND $H
HTAB
list 6
fmap 2 53
acta
REM
REM
REM
WGHT 0.071000 0.209300
FVAR 9.43017
C1 1 0.035915 0.572094 0.512411 11.00000 0.02920 0.02379 =
0.03938 -0.01704 -0.01674 0.00827
AFIX 43
H1 2 -0.031345 0.684945 0.481716 11.00000 -1.20000
AFIX 0
C2 1 0.216662 0.553716 0.586336 11.00000 0.02552 0.02140 =
0.02761 -0.01276 -0.00895 0.00477
C3 1 0.315850 0.698109 0.602460 11.00000 0.02726 0.01724 =
0.02678 -0.00994 -0.00883 0.00602
C4 1 0.471101 0.680737 0.678719 11.00000 0.02685 0.01864 =
0.02794 -0.01101 -0.00876 0.00208
AFIX 43
H4 2 0.530524 0.782718 0.687774 11.00000 -1.20000
AFIX 0
C5 1 0.538855 0.513619 0.741569 11.00000 0.02427 0.02070 =
0.02638 -0.00999 -0.00815 0.00346
C6 1 0.450635 0.365888 0.725505 11.00000 0.02554 0.01885 =
0.02764 -0.00932 -0.00817 0.00327
C7 1 0.290094 0.386832 0.650941 11.00000 0.02676 0.01874 =
0.03160 -0.01244 -0.01046 0.00296
AFIX 43
H7 2 0.228245 0.284508 0.643620 11.00000 -1.20000
AFIX 0
N1 3 0.261008 0.881057 0.537582 11.00000 0.02761 0.01960 =
0.03189 -0.01066 -0.01171 0.00460
O1 4 0.265733 0.994882 0.586985 11.00000 0.03958 0.01964 =
0.04553 -0.01693 -0.01851 0.00803
O2 4 0.221966 0.912521 0.437211 11.00000 0.04185 0.02615 =
0.03261 -0.00705 -0.01826 0.00384
C8 1 0.696567 0.500146 0.828105 11.00000 0.02816 0.01665 =
0.02889 -0.01096 -0.01049 0.00534
O3 4 0.860163 0.593045 0.808158 11.00000 0.03086 0.02262 =
0.03555 -0.01015 -0.01378 0.00048
O4 4 0.627971 0.376629 0.930053 11.00000 0.03271 0.02016 =
0.02722 -0.00693 -0.01262 0.00163
C9 1 0.782607 0.341121 1.015035 11.00000 0.03665 0.02654 =
0.03108 -0.00851 -0.01706 0.00452
AFIX 137
H9A 2 0.933156 0.306373 0.979732 11.00000 -1.50000
H9B 2 0.722258 0.245232 1.085262 11.00000 -1.50000
H9C 2 0.796944 0.447755 1.037561 11.00000 -1.50000
AFIX 0
C10 1 0.526710 0.181109 0.784642 11.00000 0.03059 0.01926 =
0.03191 -0.00943 -0.01366 0.00212
O5 4 0.398966 0.058335 0.825059 11.00000 0.03861 0.02226 =
0.06048 -0.00176 -0.02457 -0.00230
O6 4 0.750632 0.170461 0.783932 11.00000 0.02971 0.01854 =
0.03332 -0.00973 -0.01288 0.00656
C11 1 0.837390 -0.002497 0.843837 11.00000 0.03726 0.01997 =
0.04427 -0.00844 -0.01733 0.00991
AFIX 137
H11A 2 0.806798 -0.087882 0.804802 11.00000 -1.50000
H11B 2 0.761355 -0.039755 0.926402 11.00000 -1.50000
H11C 2 1.002594 0.003374 0.840751 11.00000 -1.50000
AFIX 0
HKLF 4
REM herges176_a.res in P-1
REM R1 = 0.0429 for 2042 Fo > 4sig(Fo) and 0.0458 for all 2211 data
REM 165 parameters refined using 0 restraints
END
WGHT 0.0710 0.2092
REM Instructions for potential hydrogen bonds
HTAB C9 O5_$1
HTAB C11 O3_$2
HTAB C11 O5_$3
REM Highest difference peak 0.371, deepest hole -0.301, 1-sigma level 0.055
Q1 1 -0.0881 0.6559 0.5315 11.00000 0.05 0.37
Q2 1 0.1217 0.6592 0.4235 11.00000 0.05 0.35
Q3 1 0.6133 0.5013 0.7837 11.00000 0.05 0.28
Q4 1 0.2597 0.6334 0.5954 11.00000 0.05 0.27
Q5 1 0.1385 0.5642 0.5452 11.00000 0.05 0.24
;
_shelx_res_checksum 54454
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.0359(3) 0.5721(2) 0.51241(15) 0.0281(3) Uani d 1 . .
H H1 -0.031345 0.684945 0.481716 0.034 Uiso calc 1 . .
C C2 0.2167(3) 0.55372(19) 0.58634(13) 0.0233(3) Uani d 1 . .
C C3 0.3159(3) 0.69811(19) 0.60246(13) 0.0227(3) Uani d 1 . .
C C4 0.4711(3) 0.6807(2) 0.67872(13) 0.0231(3) Uani d 1 . .
H H4 0.530524 0.782718 0.687774 0.028 Uiso calc 1 . .
C C5 0.5389(3) 0.5136(2) 0.74157(13) 0.0228(3) Uani d 1 . .
C C6 0.4506(3) 0.36589(19) 0.72551(13) 0.0232(3) Uani d 1 . .
C C7 0.2901(3) 0.3868(2) 0.65094(14) 0.0240(3) Uani d 1 . .
H H7 0.228245 0.284508 0.643620 0.029 Uiso calc 1 . .
N N1 0.2610(2) 0.88106(17) 0.53758(12) 0.0251(3) Uani d 1 . .
O O1 0.2657(2) 0.99488(15) 0.58698(11) 0.0322(3) Uani d 1 . .
O O2 0.2220(2) 0.91252(15) 0.43721(11) 0.0326(3) Uani d 1 . .
C C8 0.6966(3) 0.50015(19) 0.82811(13) 0.0232(3) Uani d 1 . .
O O3 0.8602(2) 0.59305(14) 0.80816(10) 0.0283(3) Uani d 1 . .
O O4 0.62797(19) 0.37663(14) 0.93005(9) 0.0258(3) Uani d 1 . .
C C9 0.7826(3) 0.3411(2) 1.01503(15) 0.0302(4) Uani d 1 . .
H H9A 0.933156 0.306373 0.979732 0.045 Uiso calc 1 . .
H H9B 0.722258 0.245232 1.085262 0.045 Uiso calc 1 . .
H H9C 0.796944 0.447755 1.037561 0.045 Uiso calc 1 . .
C C10 0.5267(3) 0.1811(2) 0.78464(14) 0.0259(3) Uani d 1 . .
O O5 0.3990(2) 0.05833(16) 0.82506(13) 0.0407(3) Uani d 1 . .
O O6 0.75063(19) 0.17046(14) 0.78393(10) 0.0261(3) Uani d 1 . .
C C11 0.8374(3) -0.0025(2) 0.84384(17) 0.0332(4) Uani d 1 . .
H H11A 0.806798 -0.087882 0.804802 0.050 Uiso calc 1 . .
H H11B 0.761355 -0.039755 0.926402 0.050 Uiso calc 1 . .
H H11C 1.002594 0.003374 0.840751 0.050 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
C1 0.0292(8) 0.0238(8) 0.0394(9) 0.0083(6) -0.0167(7) -0.0170(6)
C2 0.0255(7) 0.0214(7) 0.0276(7) 0.0048(5) -0.0089(6) -0.0128(6)
C3 0.0273(7) 0.0172(7) 0.0268(7) 0.0060(5) -0.0088(6) -0.0099(5)
C4 0.0268(7) 0.0186(7) 0.0279(7) 0.0021(5) -0.0088(6) -0.0110(6)
C5 0.0243(7) 0.0207(7) 0.0264(7) 0.0035(5) -0.0081(6) -0.0100(6)
C6 0.0255(7) 0.0188(7) 0.0276(7) 0.0033(5) -0.0082(6) -0.0093(6)
C7 0.0268(7) 0.0187(7) 0.0316(8) 0.0030(5) -0.0105(6) -0.0124(6)
N1 0.0276(6) 0.0196(6) 0.0319(7) 0.0046(5) -0.0117(5) -0.0107(5)
O1 0.0396(7) 0.0196(6) 0.0455(7) 0.0080(4) -0.0185(5) -0.0169(5)
O2 0.0418(7) 0.0262(6) 0.0326(6) 0.0038(5) -0.0183(5) -0.0071(5)
C8 0.0282(7) 0.0166(7) 0.0289(7) 0.0053(5) -0.0105(6) -0.0110(6)
O3 0.0309(6) 0.0226(6) 0.0356(6) 0.0005(4) -0.0138(5) -0.0102(4)
O4 0.0327(6) 0.0202(5) 0.0272(5) 0.0016(4) -0.0126(4) -0.0069(4)
C9 0.0366(8) 0.0265(8) 0.0311(8) 0.0045(6) -0.0171(7) -0.0085(6)
C10 0.0306(8) 0.0193(7) 0.0319(8) 0.0021(6) -0.0137(6) -0.0094(6)
O5 0.0386(7) 0.0223(6) 0.0605(8) -0.0023(5) -0.0246(6) -0.0018(5)
O6 0.0297(6) 0.0185(5) 0.0333(6) 0.0066(4) -0.0129(4) -0.0097(4)
C11 0.0373(9) 0.0200(8) 0.0443(9) 0.0099(6) -0.0173(7) -0.0084(7)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 C1 H1 2_566 . 119.4 ?
C1 C1 C2 2_566 . 121.20(18) ?
C2 C1 H1 . . 119.4 ?
C3 C2 C1 . . 123.55(13) ?
C7 C2 C1 . . 121.09(13) ?
C7 C2 C3 . . 115.26(13) ?
C2 C3 N1 . . 121.38(13) ?
C4 C3 C2 . . 123.52(13) ?
C4 C3 N1 . . 115.10(12) ?
C3 C4 H4 . . 120.2 ?
C5 C4 C3 . . 119.57(13) ?
C5 C4 H4 . . 120.2 ?
C4 C5 C6 . . 118.99(13) ?
C4 C5 C8 . . 117.98(13) ?
C6 C5 C8 . . 122.98(13) ?
C5 C6 C10 . . 122.09(13) ?
C7 C6 C5 . . 120.29(13) ?
C7 C6 C10 . . 117.60(13) ?
C2 C7 H7 . . 118.9 ?
C6 C7 C2 . . 122.30(13) ?
C6 C7 H7 . . 118.9 ?
O1 N1 C3 . . 117.41(12) ?
O2 N1 C3 . . 118.67(12) ?
O2 N1 O1 . . 123.86(13) ?
O3 C8 C5 . . 123.87(14) ?
O3 C8 O4 . . 124.94(14) ?
O4 C8 C5 . . 111.17(13) ?
C8 O4 C9 . . 115.16(12) ?
O4 C9 H9A . . 109.5 ?
O4 C9 H9B . . 109.5 ?
O4 C9 H9C . . 109.5 ?
H9A C9 H9B . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
O5 C10 C6 . . 123.44(14) ?
O5 C10 O6 . . 124.79(14) ?
O6 C10 C6 . . 111.75(13) ?
C10 O6 C11 . . 115.35(12) ?
O6 C11 H11A . . 109.5 ?
O6 C11 H11B . . 109.5 ?
O6 C11 H11C . . 109.5 ?
H11A C11 H11B . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
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
C1 C1 2_566 1.383(3) ?
C1 H1 . 0.9500 ?
C1 C2 . 1.488(2) ?
C2 C3 . 1.406(2) ?
C2 C7 . 1.403(2) ?
C3 C4 . 1.388(2) ?
C3 N1 . 1.4710(19) ?
C4 H4 . 0.9500 ?
C4 C5 . 1.386(2) ?
C5 C6 . 1.398(2) ?
C5 C8 . 1.5000(19) ?
C6 C7 . 1.394(2) ?
C6 C10 . 1.502(2) ?
C7 H7 . 0.9500 ?
N1 O1 . 1.2316(17) ?
N1 O2 . 1.2208(18) ?
C8 O3 . 1.2065(19) ?
C8 O4 . 1.3335(19) ?
O4 C9 . 1.4497(18) ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C10 O5 . 1.202(2) ?
C10 O6 . 1.3268(19) ?
O6 C11 . 1.4515(18) ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C9 H9B O5 2_657 0.98 2.42 3.308(2) 149.8
C11 H11A O3 1_545 0.98 2.52 3.3650(19) 143.7
C11 H11C O5 1_655 0.98 2.39 3.364(2) 172.6
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 C1 C2 C7 2_566 . . . -11.9(3) ?
C1 C1 C2 C3 2_566 . . . 171.9(2) ?
C7 C2 C3 C4 . . . . -1.7(2) ?
C1 C2 C3 C4 . . . . 174.69(15) ?
C7 C2 C3 N1 . . . . 177.99(13) ?
C1 C2 C3 N1 . . . . -5.6(2) ?
C2 C3 C4 C5 . . . . 1.5(2) ?
N1 C3 C4 C5 . . . . -178.24(13) ?
C3 C4 C5 C6 . . . . 0.7(2) ?
C3 C4 C5 C8 . . . . -176.63(13) ?
C4 C5 C6 C7 . . . . -2.5(2) ?
C8 C5 C6 C7 . . . . 174.67(14) ?
C4 C5 C6 C10 . . . . 176.16(14) ?
C8 C5 C6 C10 . . . . -6.6(2) ?
C5 C6 C7 C2 . . . . 2.3(2) ?
C10 C6 C7 C2 . . . . -176.45(14) ?
C3 C2 C7 C6 . . . . -0.2(2) ?
C1 C2 C7 C6 . . . . -176.69(14) ?
C4 C3 N1 O2 . . . . 146.08(15) ?
C2 C3 N1 O2 . . . . -33.6(2) ?
C4 C3 N1 O1 . . . . -31.3(2) ?
C2 C3 N1 O1 . . . . 148.99(15) ?
C4 C5 C8 O3 . . . . -43.2(2) ?
C6 C5 C8 O3 . . . . 139.53(16) ?
C4 C5 C8 O4 . . . . 134.90(14) ?
C6 C5 C8 O4 . . . . -42.34(19) ?
O3 C8 O4 C9 . . . . -8.0(2) ?
C5 C8 O4 C9 . . . . 173.88(12) ?
C7 C6 C10 O5 . . . . -40.6(2) ?
C5 C6 C10 O5 . . . . 140.64(18) ?
C7 C6 C10 O6 . . . . 137.89(15) ?
C5 C6 C10 O6 . . . . -40.8(2) ?
O5 C10 O6 C11 . . . . -4.0(2) ?
C6 C10 O6 C11 . . . . 177.52(13) ?