#------------------------------------------------------------------------------
#$Date: 2023-04-05 14:17:41 +0300 (Wed, 05 Apr 2023) $
#$Revision: 282401 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/27/2022717.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_2022717
loop_
_publ_author_name
'Archana, Sreeramapura D.'
'Foro, Sabine'
'Yathirajan, Hemmige S.'
'Kiran Kumar, Haruvegowda'
'Balerao, Rishik'
'Butcher, Ray J.'
_publ_section_title
;
Syntheses, crystal structures and Hirshfeld surface analysis of three
salts of 1-(4-nitrophenyl)piperazine
;
_journal_coeditor_code VM2276
_journal_issue 4
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_page_first 373
_journal_page_last 379
_journal_paper_doi 10.1107/S2056989023002517
_journal_volume 79
_journal_year 2023
_chemical_formula_iupac 'C10 H14 N3 O2 +, C7 H5 O3 -'
_chemical_formula_moiety 'C10 H14 N3 O2 +, C7 H5 O3 -'
_chemical_formula_sum 'C17 H19 N3 O5'
_chemical_formula_weight 345.35
_chemical_name_common
;
4-(4-Nitrophenyl)piperazin-1-ium salicylate
;
_chemical_name_systematic
;
4-(4-Nitrophenyl)piperazin-1-ium 2-hydroxybenzoate
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_Hall '-P 2yn'
_space_group_name_H-M_alt 'P 1 21/n 1'
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary dual
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-2018/3
_cell_angle_alpha 90
_cell_angle_beta 90.132(4)
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 7.0018(3)
_cell_length_b 7.3938(3)
_cell_length_c 31.5310(10)
_cell_measurement_reflns_used 3505
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 27.71
_cell_measurement_theta_min 2.57
_cell_volume 1632.35(11)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature 293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur with Sapphire CCD
;
_diffrn_measurement_method
;
Rotation method data acquisition using omega scans.
;
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0156
_diffrn_reflns_av_unetI/netI 0.0264
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_k_min -5
_diffrn_reflns_limit_l_max 41
_diffrn_reflns_limit_l_min -30
_diffrn_reflns_number 6955
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 27.749
_diffrn_reflns_theta_min 2.584
_diffrn_source 'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu 0.105
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.88593
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour yellow
_exptl_crystal_density_diffrn 1.405
_exptl_crystal_description prism
_exptl_crystal_F_000 728
_exptl_crystal_size_max 0.480
_exptl_crystal_size_mid 0.400
_exptl_crystal_size_min 0.400
_refine_diff_density_max 0.217
_refine_diff_density_min -0.206
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.044
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 235
_refine_ls_number_reflns 3506
_refine_ls_number_restraints 3
_refine_ls_restrained_S_all 1.046
_refine_ls_R_factor_all 0.0716
_refine_ls_R_factor_gt 0.0492
_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^)+(0.0464P)^2^+0.6706P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1084
_refine_ls_wR_factor_ref 0.1191
_reflns_number_gt 2606
_reflns_number_total 3506
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file vm2276sup1.cif
_cod_data_source_block 1
_cod_original_sg_symbol_H-M 'P 21/n'
_cod_database_code 2022717
_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_estimated_absorpt_t_min 0.951
_shelx_estimated_absorpt_t_max 0.959
_shelx_hkl_file
;
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-8 0 -1 28.5714 84.8017 5
-8 0 -2 325.597 89.1205 5
-8 0 -3-0.77764 73.5001 5
-8 0 -4 372.233 97.0725 5
-8 0 -5-29.9930 79.9921 5
-8 0 -6-41.7249 72.0649 5
-8 0 -7 35.9612 85.6698 5
-8 0 -8 435.681 97.2247 5
-8 0 -9 47.3903 88.2345 5
-8 0 -10 462.621 90.0484 5
-8 0 -11-74.7577 73.4671 5
-8 0 -12 829.572 98.7435 5
-8 0 -13 23.8785 87.1576 5
-8 0 -14 162.909 93.1196 5
-8 0 -15 150.326 83.6066 5
-8 0 -16 6375.44 190.816 5
-8 -1 18-19.9814 74.6868 5
-8 -1 17 148.498 85.3818 5
-8 -1 16 392.824 84.8919 5
-8 1 15-40.2918 78.0892 5
-8 -1 15 61.6821 74.3696 5
-8 1 14 140.194 85.3843 5
-8 -1 14-198.835 80.1409 5
-8 1 13 683.127 103.755 5
-8 -1 13 583.718 93.6126 5
-8 1 12 307.643 82.2434 5
-8 -1 12 327.421 80.8715 5
-8 1 11 92.0089 82.3677 5
-8 -1 11 8.28471 88.6530 5
-8 1 10 16.0825 67.0241 5
-8 -1 10 37.9404 75.7244 5
-8 1 9 4.51757 87.9712 5
-8 -1 9 40.3425 64.4055 5
-8 1 8 231.949 71.7176 5
-8 -1 8 214.422 87.3373 5
-8 1 7 100.228 91.1973 5
-8 -1 7 7.07490 76.6526 5
-8 1 6 78.9482 74.4159 5
-8 -1 6 92.1523 70.2468 5
-8 1 5 421.053 96.9745 5
-8 -1 5 570.454 95.2769 5
-8 1 4 29.4560 68.0910 5
-8 -1 4 46.2239 70.1864 5
-8 1 3 1254.06 110.904 5
-8 -1 3 1481.83 112.472 5
-8 1 2 232.305 74.3852 5
-8 -1 2 323.296 86.4284 5
-8 -1 1 860.772 96.9005 5
-8 1 1 699.727 100.641 5
-8 1 0-41.2962 74.8452 5
-8 -1 0 62.0421 84.0488 5
-8 1 -1 2919.18 133.731 5
-8 -1 -1 2823.81 134.492 5
-8 1 -2 655.112 102.209 5
-8 -1 -2 673.607 93.2659 5
-8 1 -3 756.618 87.3611 5
-8 -1 -3 653.147 98.7315 5
-8 1 -4 103.869 87.2798 5
-8 -1 -4 38.4261 65.7808 5
-8 1 -5 189.483 92.7338 5
-8 -1 -5 119.406 88.9864 5
-8 1 -6 1049.96 97.6148 5
-8 -1 -6 1229.22 115.600 5
-8 1 -7 1336.87 109.841 5
-8 -1 -7 1212.40 108.390 5
-8 1 -8 177.678 91.5300 5
-8 -1 -8 228.594 84.4292 5
-8 1 -9-41.7075 94.6132 5
-8 -1 -9 0.28288 90.0255 5
-8 1 -10 448.897 98.9766 5
-8 -1 -10 593.923 103.365 5
-8 1 -11 256.082 91.5318 5
-8 -1 -11 322.221 102.472 5
-8 1 -12 151.045 86.4131 5
-8 -1 -12 215.264 101.039 5
-8 1 -13 3118.99 139.112 5
-8 -1 -13 3316.88 154.848 5
-8 1 -14 68.2138 78.0583 5
-8 -1 -14 169.989 106.168 5
-8 1 -15 18.0155 86.9401 5
-8 1 -16 108.467 92.0964 5
-8 -2 17 67.0247 83.2062 5
-8 -2 16 100.328 64.2222 5
-8 -2 15 574.138 82.9628 5
-8 -2 14 136.873 85.9899 5
-8 2 13 363.696 100.653 5
-8 -2 13 387.441 90.3077 5
-8 2 12 565.777 83.7998 5
-8 -2 12 448.089 73.2126 5
-8 2 11 411.213 102.276 5
-8 -2 11 244.887 79.0641 5
-8 2 10 23.5553 71.4263 5
-8 -2 10 164.979 81.8296 5
-8 2 9 66.1998 95.7208 5
-8 -2 9 27.4536 76.8682 5
-8 2 8 158.701 82.1499 5
-8 -2 8 0.50389 63.8556 5
-8 2 7 526.257 99.1794 5
-8 -2 7 660.397 89.5302 5
-8 2 6 29.9389 81.1662 5
-8 -2 6-27.6489 79.6794 5
-8 2 5 47.2504 79.8736 5
-8 -2 5 49.1848 63.4605 5
-8 2 4 276.080 91.6112 5
-8 -2 4 351.392 85.0174 5
-8 2 3 49.2379 68.5699 5
-8 -2 3 132.613 82.5996 5
-8 2 2-24.1080 88.9795 5
-8 -2 2 45.9195 70.7798 5
-8 2 1 407.582 84.1584 5
-8 -2 1 323.773 86.8129 5
-8 2 0-13.6789 79.4680 5
-8 -2 0-3.09282 60.0203 5
-8 2 -1 870.183 105.658 5
-8 -2 -1 1101.76 104.171 5
-8 2 -2 231.492 73.0222 5
-8 -2 -2 226.349 73.8813 5
-8 2 -3 37.8082 80.7171 5
-8 -2 -3-0.53154 82.7401 5
-8 2 -4 504.053 97.8870 5
-8 -2 -4 339.097 81.2939 5
-8 2 -5 185.231 79.5282 5
-8 -2 -5 141.579 77.6760 5
-8 2 -6 5.26551 72.3886 5
-8 -2 -6 89.6353 90.2176 5
-8 2 -7-97.9587 85.3579 5
-8 -2 -7-34.8099 80.6724 5
-8 2 -8-27.4015 86.7021 5
-8 -2 -8-48.4024 65.1094 5
-8 -2 -9 647.839 96.6890 5
-8 2 -9 622.189 101.234 5
-8 2 -10 18.7241 84.1600 5
-8 -2 -10 353.956 97.2991 5
-8 2 -11-4.74024 74.7234 5
-8 -2 -11-79.3374 98.5264 5
-8 2 -12 413.943 81.7425 5
-8 -2 -12 332.555 102.510 5
-8 2 -13 708.112 89.1334 5
-8 -2 -13 753.969 115.616 5
-8 2 -14 82.6370 71.0445 5
-8 2 -15 1157.94 104.236 5
-8 2 -16 480.238 95.3444 5
-8 2 -17 118.507 95.1073 5
-8 3 10 226.383 101.273 5
-8 3 9 142.625 91.1483 5
-8 3 8 98.1762 83.7830 5
-8 -3 8 194.163 78.7122 5
-8 -3 7 859.082 100.152 5
-8 3 7 703.167 104.658 5
-8 3 6 134.580 75.5349 5
-8 -3 6 8.29459 73.9107 5
-8 3 5 313.711 103.562 5
-8 -3 5 326.486 69.9940 5
-8 3 4 32.9442 89.8888 5
-8 -3 4 171.960 81.6415 5
-8 3 3 1268.12 101.700 5
-8 -3 3 1454.17 106.351 5
-8 3 2 292.889 102.879 5
-8 -3 2 170.478 69.8481 5
-8 3 1 1191.31 112.520 5
-8 -3 1 943.058 100.810 5
-8 3 0 183.953 75.6576 5
-8 -3 0 274.247 70.4832 5
-8 3 -1 207.703 91.2896 5
-8 -3 -1 549.779 93.5697 5
-8 3 -2 896.279 108.579 5
-8 -3 -2 892.700 90.6831 5
-8 3 -3 20.4720 76.1364 5
-8 -3 -3-95.9859 92.6578 5
-8 3 -4-32.6451 79.7331 5
-8 -3 -4 10.4398 69.3874 5
-8 3 -5 120.202 84.7052 5
-8 -3 -5 286.861 88.8301 5
-8 3 -6 137.238 88.1818 5
-8 -3 -6 141.160 83.6299 5
-8 3 -7 349.185 88.7718 5
-8 -3 -7 114.792 77.3433 5
-8 3 -8 499.133 84.1069 5
-8 -3 -8 537.172 98.9709 5
-8 3 -9 695.477 94.2364 5
-8 -3 -9 785.737 110.748 5
-8 3 -10 280.108 90.3512 5
-8 -3 -10 67.2191 98.6315 5
-8 3 -11-138.538 86.6218 5
-8 -3 -11 33.7789 90.8263 5
-8 3 -12 258.671 89.8689 5
-8 3 -13 11.2424 86.0678 5
-8 3 -14 344.646 98.0940 5
-8 3 -15 187.406 98.5097 5
-8 4 6 557.434 111.438 5
-8 4 5 249.854 85.9962 5
-8 4 4 295.604 92.3028 5
-8 4 3-9.61937 103.337 5
-8 4 2 188.916 97.6090 5
-8 4 1 208.353 72.0339 5
-8 4 0-168.260 85.4319 5
-8 4 -1-82.7575 97.0732 5
-8 -4 -1 138.761 64.6596 5
-8 4 -2-17.3612 93.2762 5
-8 -4 -2-49.8850 80.9253 5
-8 4 -3 184.543 79.1549 5
-8 -4 -3 249.094 65.6110 5
-8 4 -4 18.1141 81.7494 5
-8 -4 -4 148.832 88.2823 5
-8 4 -5-93.4859 91.5350 5
-8 -4 -5 159.576 82.7261 5
-8 4 -6 151.058 86.9750 5
-8 -4 -6 51.1887 76.3114 5
-8 -4 -7 714.961 108.142 5
-8 -4 -8 118.904 81.1562 5
;
_shelx_hkl_checksum 10580
_shelx_res_file
;
TITL NP1 IN P2(1)/N
shelx.res
created by SHELXL-2018/3 at 13:01:29 on 03-Dec-2022
CELL 0.71073 7.00180 7.39380 31.53100 90.00000 90.13200 90.00000
ZERR 4 0.00030 0.00030 0.00100 0.00000 0.00400 0.00000
LATT 1
SYMM -X+ 0.50000, Y+ 0.50000, -Z+ 0.50000
SFAC C H N O
UNIT 68 76 12 20
OMIT -1 0 7
OMIT 1 1 23
OMIT 0 1 29
LIST 4
rem SHEL 32 0.83
SIZE 0.48 0.40 0.40
L.S. 14
CONF
ACTA
BOND $H
htab
DFIX 0.86 0.02 N2 H21 N2 H22
DFIX 0.82 0.02 O5 H5O
HTAB C8 O5_$1
HTAB C9 O5_$2
HTAB N2 O3_$3
HTAB N2 O4
HTAB O5 O4
EQIV $1 -x+1/2, y-1/2, -z+1/2
EQIV $2 x+1, y, z
EQIV $3 -x+3/2, y+1/2, -z+1/2
omit 0 2 4 ! 21478.58 27453.87 4.48 1.000 3.35
omit -1 2 3 ! 17209.50 21481.80 4.13 0.885 3.12
omit -1 1 2 ! 14906.13 18258.57 3.76 0.816 4.84
omit -1 1 5 ! 15323.62 18464.62 3.30 0.820 3.96
omit -1 1 4 ! 12990.54 15328.97 2.96 0.747 4.28
omit -1 1 1 ! 7993.35 9352.22 2.94 0.584 5.02
omit -1 0 1 ! 4359.80 5001.02 2.72 0.588 6.84
WGHT 0.046400 0.670600
FVAR 4.07167
C1 1 0.947969 0.430514 0.403348 11.00000 0.03567 0.03132 =
0.02949 -0.00132 -0.00322 0.00048
C2 1 1.144775 0.451574 0.407829 11.00000 0.03692 0.05245 =
0.03668 0.00801 -0.00122 0.00047
AFIX 43
H2 2 1.214403 0.506875 0.386354 11.00000 -1.20000
AFIX 0
C3 1 1.237225 0.391234 0.443782 11.00000 0.03575 0.06465 =
0.04394 0.00365 -0.00846 0.00546
AFIX 43
H3 2 1.368446 0.406601 0.446657 11.00000 -1.20000
AFIX 0
C4 1 1.134396 0.308172 0.475388 11.00000 0.05028 0.04124 =
0.03152 0.00101 -0.01066 0.00722
C5 1 0.940104 0.286641 0.472243 11.00000 0.05315 0.04446 =
0.03285 0.00519 -0.00157 -0.00667
AFIX 43
H5 2 0.871988 0.231148 0.493930 11.00000 -1.20000
AFIX 0
C6 1 0.847586 0.348547 0.436447 11.00000 0.03658 0.05072 =
0.03736 0.00479 -0.00528 -0.00808
AFIX 43
H6 2 0.715817 0.335531 0.434273 11.00000 -1.20000
AFIX 0
C7 1 0.691485 0.610501 0.372456 11.00000 0.03384 0.04701 =
0.03200 -0.00049 -0.00280 0.00307
AFIX 23
H7A 2 0.742612 0.729932 0.378242 11.00000 -1.20000
H7B 2 0.616032 0.573640 0.396727 11.00000 -1.20000
AFIX 0
C8 1 0.565079 0.618647 0.333632 11.00000 0.03541 0.04049 =
0.03816 0.00093 -0.00725 -0.00162
AFIX 23
H8A 2 0.499976 0.503859 0.330013 11.00000 -1.20000
H8B 2 0.469135 0.711902 0.337361 11.00000 -1.20000
AFIX 0
C9 1 0.835290 0.522632 0.290129 11.00000 0.04526 0.05381 =
0.02793 -0.00023 -0.00215 -0.00242
AFIX 23
H9A 2 0.909732 0.550803 0.265077 11.00000 -1.20000
H9B 2 0.780236 0.403244 0.286470 11.00000 -1.20000
AFIX 0
C10 1 0.963190 0.524402 0.328923 11.00000 0.03586 0.04535 =
0.03013 0.00096 -0.00143 0.00026
AFIX 23
H10A 2 1.064043 0.435557 0.325689 11.00000 -1.20000
H10B 2 1.021744 0.642570 0.332035 11.00000 -1.20000
AFIX 0
C11 1 0.310647 0.549827 0.166166 11.00000 0.03490 0.02872 =
0.03441 0.00359 -0.00431 0.00142
C12 1 0.128147 0.622849 0.171735 11.00000 0.03411 0.03092 =
0.03166 0.00266 -0.00333 -0.00082
C13 1 -0.008372 0.607053 0.139738 11.00000 0.03476 0.04117 =
0.04624 0.00447 -0.00780 0.00031
AFIX 43
H13 2 -0.130219 0.654106 0.143688 11.00000 -1.20000
AFIX 0
C14 1 0.036979 0.521897 0.102310 11.00000 0.05733 0.04109 =
0.04001 0.00092 -0.01908 -0.00376
AFIX 43
H14 2 -0.055100 0.510333 0.081179 11.00000 -1.20000
AFIX 0
C15 1 0.218112 0.453413 0.095840 11.00000 0.07270 0.04357 =
0.03366 -0.00499 -0.00497 0.00772
AFIX 43
H15 2 0.248883 0.397864 0.070291 11.00000 -1.20000
AFIX 0
C16 1 0.352672 0.468119 0.127547 11.00000 0.04750 0.04188 =
0.04087 0.00055 0.00050 0.01237
AFIX 43
H16 2 0.474660 0.422323 0.123046 11.00000 -1.20000
AFIX 0
C17 1 0.457658 0.557734 0.200973 11.00000 0.03685 0.03511 =
0.04291 0.00736 -0.00757 -0.00073
N1 3 0.849879 0.482552 0.366557 11.00000 0.03378 0.04337 =
0.02672 0.00364 -0.00252 0.00156
N2 3 0.680231 0.658646 0.295337 11.00000 0.04415 0.04311 =
0.03328 0.00494 -0.01501 -0.00783
H21 2 0.734855 0.771112 0.297742 11.00000 -1.20000
H22 2 0.596744 0.659102 0.273318 11.00000 -1.20000
N3 3 1.234788 0.240313 0.512711 11.00000 0.07194 0.05901 =
0.04227 0.00596 -0.01881 0.00813
O1 4 1.142542 0.164180 0.540238 11.00000 0.09972 0.08621 =
0.04814 0.02701 -0.02040 -0.00727
O2 4 1.407630 0.265820 0.515330 11.00000 0.06577 0.14578 =
0.07941 0.03464 -0.03384 0.00746
O3 4 0.611688 0.477796 0.196758 11.00000 0.04012 0.05990 =
0.07104 0.00354 -0.01409 0.01414
O4 4 0.413476 0.651143 0.233578 11.00000 0.05173 0.06076 =
0.03750 -0.00518 -0.01749 0.00659
O5 4 0.078248 0.711576 0.207798 11.00000 0.04266 0.06085 =
0.03684 -0.00849 -0.00334 0.01064
H5O 2 0.178136 0.709938 0.223416 11.00000 -1.20000
HKLF 4
REM NP1 IN P2(1)/N
REM wR2 = 0.1191, GooF = S = 1.044, Restrained GooF = 1.046 for all data
REM R1 = 0.0492 for 2606 Fo > 4sig(Fo) and 0.0716 for all 3506 data
REM 235 parameters refined using 3 restraints
END
WGHT 0.0464 0.6706
REM Instructions for potential hydrogen bonds
HTAB C8 O5_$1
HTAB C9 O5_$2
HTAB N2 O3_$3
HTAB N2 O4
HTAB O5 O4
REM Highest difference peak 0.217, deepest hole -0.206, 1-sigma level 0.038
Q1 1 1.3581 0.1482 0.5035 11.00000 0.05 0.22
Q2 1 0.3871 0.5785 0.1786 11.00000 0.05 0.19
Q3 1 0.9067 0.5244 0.3501 11.00000 0.05 0.17
Q4 1 1.0239 0.4957 0.4118 11.00000 0.05 0.16
Q5 1 0.6250 0.6263 0.3538 11.00000 0.05 0.15
Q6 1 0.0485 0.5919 0.1590 11.00000 0.05 0.15
Q7 1 0.0650 0.6454 0.1538 11.00000 0.05 0.15
Q8 1 1.0527 0.2590 0.4705 11.00000 0.05 0.15
Q9 1 0.4755 0.6584 0.2551 11.00000 0.05 0.15
Q10 1 0.3667 0.8102 0.2319 11.00000 0.05 0.14
Q11 1 0.2368 0.6267 0.1639 11.00000 0.05 0.14
Q12 1 1.1801 0.2894 0.4527 11.00000 0.05 0.14
Q13 1 0.8918 0.5246 0.3104 11.00000 0.05 0.14
Q14 1 0.1204 0.4570 0.1124 11.00000 0.05 0.14
Q15 1 1.1835 0.2348 0.4881 11.00000 0.05 0.14
Q16 1 0.2137 0.5380 0.1754 11.00000 0.05 0.13
Q17 1 1.1997 0.3805 0.4204 11.00000 0.05 0.13
Q18 1 0.3238 0.4960 0.1537 11.00000 0.05 0.13
Q19 1 1.0568 0.3825 0.4009 11.00000 0.05 0.13
Q20 1 0.9020 0.4627 0.3852 11.00000 0.05 0.12
;
_shelx_res_checksum 66044
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.9480(2) 0.4305(2) 0.40335(5) 0.0322(4) Uani d 1 . .
C C2 1.1448(3) 0.4516(3) 0.40783(6) 0.0420(4) Uani d 1 . .
H H2 1.214403 0.506875 0.386354 0.050 Uiso calc 1 . .
C C3 1.2372(3) 0.3912(3) 0.44378(6) 0.0481(5) Uani d 1 . .
H H3 1.368446 0.406601 0.446657 0.058 Uiso calc 1 . .
C C4 1.1344(3) 0.3082(3) 0.47539(5) 0.0410(4) Uani d 1 . .
C C5 0.9401(3) 0.2866(3) 0.47224(6) 0.0435(4) Uani d 1 . .
H H5 0.871988 0.231148 0.493930 0.052 Uiso calc 1 . .
C C6 0.8476(3) 0.3485(3) 0.43645(6) 0.0416(4) Uani d 1 . .
H H6 0.715817 0.335531 0.434273 0.050 Uiso calc 1 . .
C C7 0.6915(2) 0.6105(3) 0.37246(5) 0.0376(4) Uani d 1 . .
H H7A 0.742612 0.729932 0.378242 0.045 Uiso calc 1 . .
H H7B 0.616032 0.573640 0.396727 0.045 Uiso calc 1 . .
C C8 0.5651(2) 0.6186(3) 0.33363(5) 0.0380(4) Uani d 1 . .
H H8A 0.499976 0.503859 0.330013 0.046 Uiso calc 1 . .
H H8B 0.469135 0.711902 0.337361 0.046 Uiso calc 1 . .
C C9 0.8353(3) 0.5226(3) 0.29013(5) 0.0423(4) Uani d 1 . .
H H9A 0.909732 0.550803 0.265077 0.051 Uiso calc 1 . .
H H9B 0.780236 0.403244 0.286470 0.051 Uiso calc 1 . .
C C10 0.9632(2) 0.5244(3) 0.32892(5) 0.0371(4) Uani d 1 . .
H H10A 1.064043 0.435557 0.325689 0.045 Uiso calc 1 . .
H H10B 1.021744 0.642570 0.332035 0.045 Uiso calc 1 . .
C C11 0.3106(2) 0.5498(2) 0.16617(5) 0.0327(4) Uani d 1 . .
C C12 0.1281(2) 0.6228(2) 0.17173(5) 0.0322(4) Uani d 1 . .
C C13 -0.0084(3) 0.6071(3) 0.13974(6) 0.0407(4) Uani d 1 . .
H H13 -0.130219 0.654106 0.143688 0.049 Uiso calc 1 . .
C C14 0.0370(3) 0.5219(3) 0.10231(6) 0.0462(5) Uani d 1 . .
H H14 -0.055100 0.510333 0.081179 0.055 Uiso calc 1 . .
C C15 0.2181(3) 0.4534(3) 0.09584(6) 0.0500(5) Uani d 1 . .
H H15 0.248883 0.397864 0.070291 0.060 Uiso calc 1 . .
C C16 0.3527(3) 0.4681(3) 0.12755(6) 0.0434(5) Uani d 1 . .
H H16 0.474660 0.422323 0.123046 0.052 Uiso calc 1 . .
C C17 0.4577(2) 0.5577(2) 0.20097(6) 0.0383(4) Uani d 1 . .
N N1 0.84988(19) 0.4826(2) 0.36656(4) 0.0346(3) Uani d 1 . .
N N2 0.6802(2) 0.6586(2) 0.29534(5) 0.0402(4) Uani d 1 . .
H H21 0.735(3) 0.771(2) 0.2977(6) 0.048 Uiso d 1 . .
H H22 0.597(2) 0.659(3) 0.2733(5) 0.048 Uiso d 1 . .
N N3 1.2348(3) 0.2403(3) 0.51271(6) 0.0578(5) Uani d 1 . .
O O1 1.1425(3) 0.1642(3) 0.54024(5) 0.0781(5) Uani d 1 . .
O O2 1.4076(3) 0.2658(3) 0.51533(6) 0.0970(7) Uani d 1 . .
O O3 0.61169(19) 0.4778(2) 0.19676(5) 0.0570(4) Uani d 1 . .
O O4 0.41348(19) 0.6511(2) 0.23358(4) 0.0500(4) Uani d 1 . .
O O5 0.07825(18) 0.7116(2) 0.20780(4) 0.0468(3) Uani d 1 . .
H H5O 0.178(2) 0.710(3) 0.2234(6) 0.056 Uiso d 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 0.0357(9) 0.0313(9) 0.0295(8) 0.0005(7) -0.0032(7) -0.0013(7)
C2 0.0369(9) 0.0525(11) 0.0367(9) 0.0005(8) -0.0012(7) 0.0080(8)
C3 0.0357(9) 0.0647(13) 0.0439(11) 0.0055(9) -0.0085(8) 0.0037(10)
C4 0.0503(11) 0.0412(10) 0.0315(9) 0.0072(9) -0.0107(8) 0.0010(8)
C5 0.0532(11) 0.0445(11) 0.0329(9) -0.0067(9) -0.0016(8) 0.0052(8)
C6 0.0366(9) 0.0507(11) 0.0374(9) -0.0081(8) -0.0053(7) 0.0048(8)
C7 0.0338(9) 0.0470(11) 0.0320(9) 0.0031(8) -0.0028(7) -0.0005(8)
C8 0.0354(9) 0.0405(10) 0.0382(9) -0.0016(8) -0.0072(7) 0.0009(8)
C9 0.0453(10) 0.0538(12) 0.0279(9) -0.0024(9) -0.0022(7) -0.0002(8)
C10 0.0359(9) 0.0453(10) 0.0301(9) 0.0003(8) -0.0014(7) 0.0010(8)
C11 0.0349(9) 0.0287(8) 0.0344(9) 0.0014(7) -0.0043(7) 0.0036(7)
C12 0.0341(8) 0.0309(9) 0.0317(8) -0.0008(7) -0.0033(7) 0.0027(7)
C13 0.0348(9) 0.0412(10) 0.0462(10) 0.0003(8) -0.0078(8) 0.0045(8)
C14 0.0573(12) 0.0411(11) 0.0400(10) -0.0038(9) -0.0191(9) 0.0009(8)
C15 0.0727(14) 0.0436(11) 0.0337(10) 0.0077(10) -0.0050(9) -0.0050(8)
C16 0.0475(11) 0.0419(10) 0.0409(10) 0.0124(9) 0.0005(8) 0.0005(8)
C17 0.0369(9) 0.0351(9) 0.0429(10) -0.0007(8) -0.0076(8) 0.0074(8)
N1 0.0338(7) 0.0434(8) 0.0267(7) 0.0016(6) -0.0025(6) 0.0036(6)
N2 0.0442(9) 0.0431(9) 0.0333(8) -0.0078(7) -0.0150(6) 0.0049(7)
N3 0.0719(13) 0.0590(11) 0.0423(10) 0.0081(10) -0.0188(9) 0.0060(9)
O1 0.0997(13) 0.0862(13) 0.0481(9) -0.0073(11) -0.0204(9) 0.0270(9)
O2 0.0658(11) 0.1458(19) 0.0794(13) 0.0075(12) -0.0338(9) 0.0346(12)
O3 0.0401(8) 0.0599(9) 0.0710(10) 0.0141(7) -0.0141(7) 0.0035(8)
O4 0.0517(8) 0.0608(9) 0.0375(7) 0.0066(7) -0.0175(6) -0.0052(7)
O5 0.0427(7) 0.0608(9) 0.0368(7) 0.0106(7) -0.0033(5) -0.0085(6)
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 118.13(15) ?
C2 C1 N1 . . 122.42(15) ?
C6 C1 N1 . . 119.41(15) ?
C3 C2 C1 . . 120.64(17) ?
C3 C2 H2 . . 119.7 ?
C1 C2 H2 . . 119.7 ?
C4 C3 C2 . . 119.66(17) ?
C4 C3 H3 . . 120.2 ?
C2 C3 H3 . . 120.2 ?
C5 C4 C3 . . 121.31(16) ?
C5 C4 N3 . . 119.60(18) ?
C3 C4 N3 . . 119.09(18) ?
C4 C5 C6 . . 118.97(18) ?
C4 C5 H5 . . 120.5 ?
C6 C5 H5 . . 120.5 ?
C5 C6 C1 . . 121.28(17) ?
C5 C6 H6 . . 119.4 ?
C1 C6 H6 . . 119.4 ?
N1 C7 C8 . . 111.35(14) ?
N1 C7 H7A . . 109.4 ?
C8 C7 H7A . . 109.4 ?
N1 C7 H7B . . 109.4 ?
C8 C7 H7B . . 109.4 ?
H7A C7 H7B . . 108.0 ?
N2 C8 C7 . . 110.44(14) ?
N2 C8 H8A . . 109.6 ?
C7 C8 H8A . . 109.6 ?
N2 C8 H8B . . 109.6 ?
C7 C8 H8B . . 109.6 ?
H8A C8 H8B . . 108.1 ?
N2 C9 C10 . . 109.57(14) ?
N2 C9 H9A . . 109.8 ?
C10 C9 H9A . . 109.8 ?
N2 C9 H9B . . 109.8 ?
C10 C9 H9B . . 109.8 ?
H9A C9 H9B . . 108.2 ?
N1 C10 C9 . . 109.44(14) ?
N1 C10 H10A . . 109.8 ?
C9 C10 H10A . . 109.8 ?
N1 C10 H10B . . 109.8 ?
C9 C10 H10B . . 109.8 ?
H10A C10 H10B . . 108.2 ?
C16 C11 C12 . . 118.20(15) ?
C16 C11 C17 . . 120.64(16) ?
C12 C11 C17 . . 121.15(15) ?
O5 C12 C13 . . 117.97(15) ?
O5 C12 C11 . . 121.87(14) ?
C13 C12 C11 . . 120.15(16) ?
C14 C13 C12 . . 120.03(17) ?
C14 C13 H13 . . 120.0 ?
C12 C13 H13 . . 120.0 ?
C13 C14 C15 . . 120.56(17) ?
C13 C14 H14 . . 119.7 ?
C15 C14 H14 . . 119.7 ?
C16 C15 C14 . . 119.40(18) ?
C16 C15 H15 . . 120.3 ?
C14 C15 H15 . . 120.3 ?
C15 C16 C11 . . 121.61(17) ?
C15 C16 H16 . . 119.2 ?
C11 C16 H16 . . 119.2 ?
O3 C17 O4 . . 123.89(16) ?
O3 C17 C11 . . 119.89(17) ?
O4 C17 C11 . . 116.22(15) ?
C1 N1 C10 . . 117.67(13) ?
C1 N1 C7 . . 116.15(13) ?
C10 N1 C7 . . 112.18(13) ?
C8 N2 C9 . . 110.67(14) ?
C8 N2 H21 . . 109.9(13) ?
C9 N2 H21 . . 108.5(12) ?
C8 N2 H22 . . 105.9(12) ?
C9 N2 H22 . . 112.8(13) ?
H21 N2 H22 . . 109.1(18) ?
O1 N3 O2 . . 123.11(18) ?
O1 N3 C4 . . 118.53(19) ?
O2 N3 C4 . . 118.3(2) ?
C12 O5 H5O . . 105.3(15) ?
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 C2 . 1.394(2) ?
C1 C6 . 1.398(2) ?
C1 N1 . 1.401(2) ?
C2 C3 . 1.378(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.375(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.373(3) ?
C4 N3 . 1.458(2) ?
C5 C6 . 1.378(2) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 N1 . 1.470(2) ?
C7 C8 . 1.510(2) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 N2 . 1.483(2) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 N2 . 1.489(2) ?
C9 C10 . 1.514(2) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 N1 . 1.462(2) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C16 . 1.391(2) ?
C11 C12 . 1.399(2) ?
C11 C17 . 1.504(2) ?
C12 O5 . 1.359(2) ?
C12 C13 . 1.393(2) ?
C13 C14 . 1.375(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.381(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.376(3) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C17 O3 . 1.237(2) ?
C17 O4 . 1.277(2) ?
N2 H21 . 0.918(15) ?
N2 H22 . 0.907(15) ?
N3 O1 . 1.221(2) ?
N3 O2 . 1.227(3) ?
O5 H5O . 0.855(15) ?
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
_geom_hbond_publ_flag
C8 H8A O5 2_545 0.97 2.53 3.430(2) 155 yes
C9 H9A O5 1_655 0.97 2.47 3.407(2) 164 yes
N2 H21 O3 2_655 0.918(15) 1.876(15) 2.784(2) 169.6(18) yes
N2 H22 O4 . 0.907(15) 1.792(15) 2.6957(18) 174.0(18) yes
O5 H5O O4 . 0.855(15) 1.733(17) 2.5221(17) 152(2) yes
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
C6 C1 C2 C3 . . . . 0.7(3) ?
N1 C1 C2 C3 . . . . -177.07(17) ?
C1 C2 C3 C4 . . . . 0.5(3) ?
C2 C3 C4 C5 . . . . -1.1(3) ?
C2 C3 C4 N3 . . . . 178.25(18) ?
C3 C4 C5 C6 . . . . 0.5(3) ?
N3 C4 C5 C6 . . . . -178.85(17) ?
C4 C5 C6 C1 . . . . 0.7(3) ?
C2 C1 C6 C5 . . . . -1.3(3) ?
N1 C1 C6 C5 . . . . 176.53(17) ?
N1 C7 C8 N2 . . . . -54.0(2) ?
N2 C9 C10 N1 . . . . 59.2(2) ?
C16 C11 C12 O5 . . . . -177.19(16) ?
C17 C11 C12 O5 . . . . 3.3(3) ?
C16 C11 C12 C13 . . . . 2.3(3) ?
C17 C11 C12 C13 . . . . -177.21(16) ?
O5 C12 C13 C14 . . . . 178.56(17) ?
C11 C12 C13 C14 . . . . -1.0(3) ?
C12 C13 C14 C15 . . . . -0.8(3) ?
C13 C14 C15 C16 . . . . 1.2(3) ?
C14 C15 C16 C11 . . . . 0.3(3) ?
C12 C11 C16 C15 . . . . -2.0(3) ?
C17 C11 C16 C15 . . . . 177.55(18) ?
C16 C11 C17 O3 . . . . -6.2(3) ?
C12 C11 C17 O3 . . . . 173.34(17) ?
C16 C11 C17 O4 . . . . 173.08(17) ?
C12 C11 C17 O4 . . . . -7.4(2) ?
C2 C1 N1 C10 . . . . 12.9(2) ?
C6 C1 N1 C10 . . . . -164.78(16) ?
C2 C1 N1 C7 . . . . -124.13(18) ?
C6 C1 N1 C7 . . . . 58.1(2) ?
C9 C10 N1 C1 . . . . 163.32(15) ?
C9 C10 N1 C7 . . . . -58.00(19) ?
C8 C7 N1 C1 . . . . -164.92(15) ?
C8 C7 N1 C10 . . . . 55.73(19) ?
C7 C8 N2 C9 . . . . 56.27(19) ?
C10 C9 N2 C8 . . . . -59.12(19) ?
C5 C4 N3 O1 . . . . 0.6(3) ?
C3 C4 N3 O1 . . . . -178.8(2) ?
C5 C4 N3 O2 . . . . -177.9(2) ?
C3 C4 N3 O2 . . . . 2.7(3) ?
_cod_database_fobs_code 2022717