#------------------------------------------------------------------------------ #$Date: 2022-11-08 21:40:59 +0200 (Tue, 08 Nov 2022) $ #$Revision: 279115 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/24/41/2244163.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_2244163 loop_ _publ_author_name 'Archana, Sreeramapura D.' 'Kiran Kumar, Haruvegowda' 'Yathirajan, Hemmige S.' 'Foro, Sabine' 'Butcher, Ray J.' _publ_section_title ; The structures of eleven (4-phenyl)piperazinium salts containing organic anions ; _journal_coeditor_code HB8034 _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first 1016 _journal_page_last 1027 _journal_paper_doi 10.1107/S2056989022009057 _journal_volume 78 _journal_year 2022 _chemical_formula_iupac 'C10 H15 N2 +, C7 H4 F O2 -, H2 O' _chemical_formula_moiety 'C10 H15 N2 +, C7 H4 F O2 -, H2 O' _chemical_formula_sum 'C17 H21 F N2 O3' _chemical_formula_weight 320.36 _chemical_name_systematic ; 4-Phenylpiperazin-1-ium 4-fluorobenzoate monohydrate ; _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 mixed _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/3 _cell_angle_alpha 93.55(2) _cell_angle_beta 92.94(2) _cell_angle_gamma 94.87(2) _cell_formula_units_Z 2 _cell_length_a 6.2390(10) _cell_length_b 7.4960(10) _cell_length_c 17.817(3) _cell_measurement_reflns_used 1437 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 27.71 _cell_measurement_theta_min 2.77 _cell_volume 827.3(2) _computing_cell_refinement ; CrysAlis RED (Oxford Diffraction, 2007) ; _computing_data_collection ; CrysAlis CCD (Oxford Diffraction, 2007) ; _computing_data_reduction ; CrysAlis RED (Oxford Diffraction, 2007) ; _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 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type ; Oxford Diffraction Xcalibur with Sapphire CCD ; _diffrn_measurement_method ; \w and \f scans ; _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0329 _diffrn_reflns_av_unetI/netI 0.0547 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 4669 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.344 _diffrn_reflns_theta_min 2.893 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.61301 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (CrysalisRED; Oxford Diffraction, 2007) ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.286 _exptl_crystal_description rod _exptl_crystal_F_000 340 _exptl_crystal_size_max 0.440 _exptl_crystal_size_mid 0.320 _exptl_crystal_size_min 0.160 _refine_diff_density_max 0.273 _refine_diff_density_min -0.196 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 220 _refine_ls_number_reflns 3013 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 1.104 _refine_ls_R_factor_all 0.1634 _refine_ls_R_factor_gt 0.0898 _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^)+(0.0717P)^2^+0.6694P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1867 _refine_ls_wR_factor_ref 0.2256 _reflns_number_gt 1611 _reflns_number_total 3013 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file hb8034sup1.cif _cod_data_source_block 1 _cod_depositor_comments 'Adding full bibliography for 2244163--2244173.cif.' _cod_database_code 2244163 _cod_database_fobs_code 2244163 _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 0.959 _shelx_estimated_absorpt_t_max 0.985 _shelx_hkl_file ; 0 0 -3 1099.20 24.4859 0 0 0 4 22362.2 110.854 4 0 0 -4 22622.0 117.662 0 0 0 5 3510.85 53.9259 4 0 0 -5 3645.15 55.5867 0 0 0 -6 9446.54 96.7007 0 0 0 6 9213.11 88.6397 4 0 0 7 1083.11 40.9773 4 0 0 -7 1300.85 44.0324 0 0 0 -8 9023.74 111.243 0 0 0 8 9186.46 101.431 4 0 0 9 3530.58 71.5579 4 0 0 -9 3758.75 79.7736 0 0 0 10 417.351 38.3146 4 0 0 -10 441.216 39.9749 0 0 0 11 28.9445 30.4132 4 0 0 -11 13.8302 30.9810 0 0 0 12 55.5755 33.8627 4 0 0 -12 123.596 34.8070 0 0 0 -13-0.42204 36.5390 0 0 0 13 60.6692 36.9154 4 0 0 14 135.142 36.8724 4 0 0 -14 30.1676 40.0559 0 0 0 -15 148.921 48.9767 0 0 0 -16 96.9185 41.7732 0 0 0 -17 224.949 49.0921 0 0 0 -18 315.277 57.9676 0 0 0 -19-0.47790 51.1517 0 0 0 -20 184.702 56.7361 0 0 0 -21 74.0370 57.0251 0 0 0 -22 91.2292 66.9822 0 0 1 -22-38.2119 70.5490 0 0 1 -21 82.3733 65.7898 0 0 1 -20-40.8931 61.5095 0 0 1 -19-15.6833 51.4646 0 0 1 -18 53.7534 53.8216 0 0 1 -17-101.944 45.9630 0 0 1 -16-81.8955 39.6059 0 0 -1 15 249.418 40.0058 4 0 1 -15 186.325 55.3592 0 0 1 -14 562.344 58.1027 0 0 -1 14 447.754 47.0681 4 0 1 -13 292.543 47.6330 0 0 -1 13 216.553 36.8033 4 0 -1 12 2100.93 65.3134 4 0 1 -12 2107.04 75.3764 0 0 -1 11 12.8745 32.7563 4 0 1 -11 30.3527 29.9709 0 0 1 -10 3923.77 85.5251 0 0 -1 10 3938.16 81.0516 4 0 -1 9 16237.2 145.810 4 0 1 -9 16497.6 158.643 0 0 -1 8 6931.22 93.7818 4 0 1 -8 6686.11 96.4210 0 0 -1 7 10473.3 107.588 4 0 1 -7 9806.59 108.410 0 0 1 -6 4292.61 67.2050 0 0 -1 6 4652.59 71.0332 4 0 -1 5 98.9384 27.2604 4 0 1 -5 115.352 19.8523 0 0 1 -4 2151.94 41.7277 0 0 -1 4 2312.39 49.6087 4 0 1 -3 1386.51 32.0364 0 0 -1 3 1320.30 34.8787 4 0 -1 2 1822.70 36.3742 4 0 -1 2 1956.24 35.2248 0 0 -1 1 748.281 22.6977 0 0 -1 -1 9.65019 15.7245 0 0 -1 -2 1917.26 34.5317 0 0 -1 -3 66.4260 16.7861 0 0 -1 -4 3761.23 54.1450 0 0 1 5 2154.10 41.1982 4 0 -1 -5 2377.00 47.2603 0 0 -1 -6 209.220 17.9109 1 0 -1 -6 219.427 23.7357 0 0 1 6 191.614 26.2101 4 0 -1 -7 3028.33 61.9264 0 0 1 7 2897.54 56.9099 4 0 -1 -7 2888.50 42.5180 1 0 1 8 2158.96 57.5063 4 0 -1 -8 2314.01 58.0118 0 0 -1 -8 2020.12 36.1940 1 0 -1 -9 8720.54 116.516 0 0 -1 -9 8409.27 73.6008 1 0 1 9 8612.94 106.190 4 0 -1 -10 484.337 40.0517 0 0 1 10 537.436 41.4213 4 0 1 11 136.351 38.1086 4 0 -1 -11 235.408 35.6908 0 0 1 12 41.7993 37.9633 4 0 -1 -12 31.2005 35.5579 0 0 1 13 3092.76 85.7649 4 0 -1 -13 2888.92 88.0387 0 0 -1 -14 459.607 52.4481 0 0 -1 -15 93.7059 40.9509 0 0 -1 -16 172.729 44.8349 0 0 -1 -17 740.715 64.5315 0 0 -1 -18 23.7727 41.8417 0 0 -1 -19 28.6117 45.8421 0 0 -1 -20 106.816 53.4293 0 0 -1 -21 182.545 60.6307 0 0 -1 -22 149.455 62.9951 0 0 2 -22-58.9500 74.8519 0 0 2 -21 0.33158 70.7820 0 0 2 -20 18.0433 67.6197 0 0 2 -19-159.612 62.2076 0 0 2 -18 169.658 60.3518 0 0 2 -17 422.134 62.5975 0 0 2 -16-12.0273 44.4483 0 0 2 -15 21.1411 43.7763 0 0 -2 15 24.4112 41.2197 4 0 2 -14 42.3003 47.8363 0 0 -2 14-1.79118 39.2190 4 0 -2 13 1147.91 61.5052 4 0 2 -13 1093.43 65.8621 0 0 2 -12 384.313 48.5997 0 0 -2 12 378.304 47.7922 4 0 2 -11 530.983 48.7349 0 0 -2 11 571.387 46.3760 4 0 -2 10 315.317 42.3386 4 0 2 -10 314.446 38.8805 0 0 2 -9 6304.85 110.785 0 0 2 -9 6276.22 61.4155 2 0 -2 9 6518.67 108.765 4 0 2 -8 81.3754 16.0273 2 0 -2 8 101.529 34.4019 4 0 2 -8 95.5725 32.9105 0 0 2 -7 27.5615 23.8345 0 0 -2 7 41.9461 31.5502 4 0 -2 6 1804.83 56.7941 4 0 2 -6 1908.30 55.0233 0 0 2 -5 27.6857 22.1066 0 0 -2 5 32.8356 27.6983 4 0 2 -4 230.627 25.8526 0 0 -2 3 587.499 33.9647 0 0 -2 2 1225.00 42.5710 0 0 -2 1 38452.1 208.377 0 0 -2 0 375042. 2202.12 0 0 -2 -1 13155.7 110.135 0 0 -2 -2 3835.42 64.7481 0 0 -2 -3 10574.1 103.311 0 0 -2 -4 10792.4 107.530 0 0 -2 -5 1093.26 40.3305 0 0 -2 -6 2336.39 56.6078 0 0 -2 -7 291.184 30.5151 0 0 -2 -8 4708.59 85.5567 0 0 -2 -9 448.407 29.3462 1 0 2 9 444.571 41.6042 4 0 -2 -9 478.142 41.7446 0 0 -2 -10 386.069 39.5746 0 0 2 10 389.937 45.3787 4 0 -2 -11 208.386 38.7903 0 0 2 11 325.074 48.1645 4 0 2 12 171.618 49.6485 4 0 -2 -12 163.860 44.3846 0 0 -2 -13 1175.28 66.6443 0 0 -2 -14 9.56787 49.6470 0 0 -2 -15 306.610 55.2076 0 0 -2 -16-28.9438 55.3398 0 0 -2 -17-117.322 54.0261 0 0 -2 -18 264.274 57.7481 0 0 -2 -19-124.298 54.8681 0 0 -2 -20-46.8666 56.4788 0 0 -2 -21-48.2870 66.3669 0 0 3 -21 526.777 87.7254 0 0 3 -20-12.3758 76.7096 0 0 3 -19 39.9855 64.8258 0 0 3 -18 60.4949 54.5594 0 0 3 -17-53.1706 55.6158 0 0 3 -16 210.457 53.2372 0 0 -3 16 130.230 47.7258 4 0 -3 15-28.8906 45.4752 4 0 3 -15 87.4661 52.8565 0 0 -3 14 657.924 63.3898 4 0 3 -14 685.602 64.9828 0 0 3 -13 3341.12 108.477 0 0 -3 13 2785.89 96.1002 4 0 -3 12 39.5258 41.2602 4 0 3 -12 168.256 48.0094 0 0 3 -11-21.7772 40.5679 0 0 -3 11 23.4921 43.8178 4 0 -3 10 2613.75 82.4548 4 0 3 -10 2575.61 85.9053 0 0 3 -9 586.502 48.4074 0 0 -3 9 616.445 52.5980 4 0 3 -8 3761.09 91.4358 0 0 3 -7 4525.05 95.0237 0 0 3 -6 2607.35 70.0648 0 0 -3 5 3266.18 76.6451 0 0 -3 4 613.263 42.5075 0 0 -3 3 729.381 43.7412 0 0 -3 2 7139.11 102.257 0 0 -3 1-7.35478 28.0511 0 0 -3 0 218.074 31.4808 0 0 -3 -1 17.1949 30.5908 0 0 -3 -2 278.895 32.4633 0 0 -3 -3 14.1450 25.9214 0 0 -3 -4 2325.76 61.7142 0 0 -3 -5 29.3540 28.5549 0 0 -3 -6-5.02392 28.7831 0 0 -3 -7 387.378 37.3556 0 0 -3 -8 546.978 41.4894 0 0 -3 -9 46.5380 30.1623 0 0 -3 -10 1326.10 59.7573 0 0 -3 -11 47.4446 34.7306 0 0 3 11-18.4196 50.9104 4 0 -3 -12 1193.24 62.4250 0 0 -3 -13 1390.24 70.7799 0 0 -3 -14 451.539 56.2554 0 0 -3 -15 57.2560 46.1139 0 0 -3 -16 590.542 61.5376 0 0 -3 -17 759.279 68.1403 0 0 -3 -18-106.254 46.7420 0 0 -3 -19-2.61942 49.4661 0 0 -3 -20-84.0594 58.5201 0 0 4 -20 194.484 83.3309 0 0 4 -19-3.80821 71.1140 0 0 4 -18 101.513 68.8460 0 0 4 -17 89.3489 55.7877 0 0 4 -16-30.1599 59.0288 0 0 4 -15 70.6479 55.1895 0 0 4 -14 617.815 71.3476 0 0 4 -13 1272.47 88.9117 0 0 4 -12 906.864 75.2666 0 0 4 -11 599.751 59.9560 0 0 4 -10 233.951 49.6716 0 0 4 -9 1461.78 71.6379 0 0 4 -8 319.993 47.3742 0 0 4 -7 229.063 42.5428 0 0 -4 6 141.554 40.9794 0 0 -4 5 196.108 43.0455 0 0 -4 4 511.693 50.9391 0 0 -4 3 4820.80 104.446 0 0 -4 2 39.8506 43.4635 0 0 -4 1 279.229 47.6299 0 0 -4 0 669.163 52.2056 0 0 -4 -1 2128.68 71.2537 0 0 -4 -2-12.1177 38.3493 0 0 -4 -3 1564.96 59.9554 0 0 -4 -4 794.467 44.1953 0 0 -4 -5 308.923 34.7010 0 0 -4 -6 0.62266 28.2865 0 0 -4 -7 50.7144 31.6949 0 0 -4 -8 195.445 38.0478 0 0 -4 -9-35.9722 33.7062 0 0 -4 -10 23.6665 33.3974 0 0 -4 -11 35.8928 49.9425 0 0 -4 -12 303.893 48.5686 0 0 -4 -13 1402.02 74.7009 0 0 -4 -14 112.227 46.6612 0 0 -4 -15 535.012 61.6939 0 0 -4 -16-1.24566 50.6554 0 0 -4 -17 166.360 49.5426 0 0 -4 -18 119.042 51.8474 0 0 -4 -19-5.61352 58.6196 0 0 5 -19 119.575 83.2319 0 0 5 -18-204.332 70.1433 0 0 5 -17-1.57387 67.3816 0 0 5 -16 188.798 69.8646 0 0 5 -15-85.0876 64.3390 0 0 5 -14 210.640 64.1829 0 0 5 -13 160.717 60.4715 0 0 5 -12 730.908 70.0968 0 0 5 -11-29.6320 48.2351 0 0 5 -10 112.136 51.3760 0 0 5 -9 68.0816 46.0922 0 0 5 -8 164.788 49.1986 0 0 -5 7 27.3944 44.4655 0 0 -5 6 11.9682 44.9913 0 0 -5 5 2085.04 87.9985 0 0 -5 4 681.929 61.6698 0 0 -5 3 101.822 49.0751 0 0 -5 2 1114.68 68.7129 0 0 -5 1 287.861 56.8845 0 0 -5 0 1113.35 70.4959 0 0 -5 -1 560.855 56.2581 0 0 -5 -2-4.05269 45.1569 0 0 -5 -3 297.918 48.5635 0 0 -5 -4 3915.47 94.1972 0 0 -5 -5 227.707 39.8874 0 0 -5 -6 261.096 38.1222 0 0 -5 -7 24.4428 28.1813 0 0 -5 -8 47.8261 33.4954 0 0 -5 -9 46.6297 35.2983 0 0 -5 -10 23.7463 35.3548 0 0 -5 -11 39.7648 40.0621 0 0 -5 -12 206.859 45.9799 0 0 -5 -13 8.12863 41.8775 0 0 -5 -14 100.157 48.6066 0 0 -5 -15 189.717 49.3142 0 0 -5 -16 403.292 64.3940 0 0 -5 -17 150.108 53.0829 0 0 -5 -18-49.4629 57.2482 0 0 6 -17 79.8236 73.4792 0 0 6 -16-17.2692 64.6681 0 0 6 -15 138.249 73.2568 0 0 6 -14 154.433 64.2537 0 0 6 -13 686.057 76.8343 0 0 6 -12 658.152 71.9453 0 0 6 -11-5.98257 56.3535 0 0 6 -10 83.5116 54.6869 0 0 6 -9 20.1595 54.5783 0 0 6 -8 56.5355 47.5738 0 0 -6 7-38.8173 51.6042 0 0 -6 6 71.4753 55.1631 0 0 -6 5-58.2321 53.4375 0 0 -6 4 988.060 80.5277 0 0 -6 3 1246.80 86.4300 0 0 -6 2 168.603 65.0450 0 0 -6 1-31.4036 59.7305 0 0 -6 0 260.460 63.8391 0 0 -6 -1 160.162 57.4384 0 0 -6 -2 706.190 63.3638 0 0 -6 -3 200.493 54.7234 0 0 -6 -4 1109.49 68.8708 0 0 -6 -5 171.028 47.2287 0 0 -6 -6 37.2621 37.9235 0 0 -6 -7 73.3054 37.3599 0 0 -6 -8 26.3462 36.5866 0 0 -6 -9 16.9444 34.1298 0 0 -6 -10 35.9330 37.0072 0 0 -6 -11 134.423 41.2463 0 0 -6 -12 164.761 44.2240 0 0 -6 -13 100.172 38.8102 0 0 -6 -14 8.39195 47.6810 0 0 -6 -15 194.808 49.5741 0 0 -6 -16 90.0847 48.3869 0 0 7 -15-133.217 74.3763 0 0 7 -14-73.4412 63.1141 0 0 7 -13 259.045 66.1894 0 0 7 -12 164.822 62.4527 0 0 7 -11 108.052 62.8666 0 0 7 -10-141.186 61.6719 0 0 7 -9 14.0542 60.7437 0 0 -7 8 137.099 54.6555 0 0 -7 7 409.512 72.3913 0 0 -7 6 213.374 67.4852 0 0 -7 5 301.914 72.5763 0 0 -7 4 304.735 71.1686 0 0 -7 3 15.5390 62.6391 0 0 -7 2 63.1458 58.6018 0 0 -7 1 38.2279 60.6117 0 0 -7 0 22.0989 62.7334 0 0 -7 -1 84.5934 56.3210 0 0 -7 -2 99.2941 51.5745 0 0 -7 -3 260.691 53.6484 0 0 -7 -4 1254.27 75.6906 0 0 -7 -5 92.6732 49.6609 0 0 -7 -6 126.522 45.5340 0 0 -7 -7-4.26187 44.4865 0 0 -7 -8-124.166 37.3236 0 0 -7 -9-52.4830 39.4553 0 0 -7 -10-10.5668 42.8483 0 0 -7 -11 9.04493 40.8007 0 0 -7 -12-40.8639 40.2937 0 0 -7 -13-61.1112 43.0027 0 0 8 -12 221.584 74.1330 0 0 8 -11-21.7926 79.8550 0 0 8 -10-131.944 64.9132 0 0 8 -9 62.2633 74.2298 0 0 -8 8 35.1550 69.9584 0 0 -8 7-45.6433 70.9589 0 0 -8 6 136.863 73.7586 0 0 -8 5 18.2793 68.9417 0 0 -8 4 137.522 74.2690 0 0 -8 3 24.8403 67.1666 0 0 -8 2 366.950 75.6022 0 0 -8 1 139.881 68.5003 0 0 -8 0 28.6337 65.3179 0 0 -8 -1 27.5525 67.1860 0 0 -8 -2 243.755 67.7801 0 0 -8 -3 177.658 58.1019 0 0 -8 -4 2.20909 48.6090 0 0 -8 -5-27.7990 49.3442 0 0 -8 -6 125.143 50.1592 0 0 -8 -7-82.2136 47.8160 0 0 -8 -8 24.8065 42.5720 0 0 -8 -9-23.0354 43.9021 0 0 -8 -10 0.20088 46.7460 0 0 -9 7-2.72016 76.9815 0 0 -9 6 216.334 79.9138 0 0 -9 5 101.442 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66.6356 2 -7 5 5 264.353 171.351 4 -7 5 4-244.655 170.759 4 7 -5 -2 13.7156 62.4772 5 7 -5 -1 133.656 61.4402 5 7 -5 0 192.835 53.5025 5 7 -5 1-68.5136 55.3937 5 7 -5 2 273.256 56.7237 5 7 -5 3 315.435 56.7493 5 -7 4 7 435.478 140.953 4 -7 4 6 68.3257 133.615 4 7 -4 -5 125.459 68.8844 5 -7 4 4-205.504 127.548 4 7 -4 -4 379.579 69.1333 5 7 -4 -3 12.1497 67.0574 5 7 -4 -2 28.2904 63.9191 5 7 -4 -1-128.122 62.5057 5 7 -4 0 207.501 56.3130 5 7 -4 1 48.7191 47.5219 5 7 -4 2 29.1879 50.5098 5 7 -4 3 163.410 52.0857 5 7 -4 4 157.054 56.0715 5 7 -4 5 129.790 54.5587 5 -7 3 9 501.181 114.526 4 -7 3 8 52.3724 118.326 4 7 -3 -6 12.4362 62.6371 5 -7 3 5 109.038 105.563 4 7 -3 -5 580.976 63.0155 5 7 -3 -4 205.555 63.5235 5 7 -3 -3 35.5491 64.9471 5 7 -3 -2 164.925 60.1368 5 7 -3 -1 14.0787 57.9550 5 7 -3 1 87.7107 55.9893 5 7 -3 2 117.760 48.6768 5 7 -3 3-42.3054 48.9356 5 7 -3 4-22.0965 50.1739 5 7 -3 5 222.378 54.2304 5 7 -3 6 151.869 52.6680 5 7 -3 7-100.402 56.2992 5 -7 2 10 789.128 107.323 4 -7 2 9 419.337 102.442 4 -7 2 8 338.392 100.755 4 -7 2 7-123.600 96.0604 4 -7 2 6-185.746 93.2540 4 7 -2 -5 19.4310 58.9679 5 7 -2 -4 216.535 59.3220 5 7 -2 -3 227.877 59.6507 5 7 -2 -2 7.58439 61.5751 5 7 -2 -1 233.310 59.3182 5 7 -2 0 89.0739 57.3105 5 7 -2 1-24.9315 56.3846 5 7 -2 2 44.0280 55.0206 5 7 -2 3 261.138 54.4765 5 7 -2 4 496.653 51.0125 5 7 -2 5 84.8545 48.9451 5 7 -2 6 4.90298 52.5573 5 7 -2 7 107.167 54.6368 5 7 -2 8 273.382 59.2246 5 -7 1 11 656.690 103.685 4 -7 1 10 451.831 102.187 4 -7 1 9 292.422 99.0126 4 -7 1 8-126.820 89.8527 4 7 -1 -6 4.90830 58.9365 2 7 -1 -5 18.3551 62.0938 2 7 -1 -4-91.3521 61.2162 2 7 -1 -3-28.5009 55.2504 2 7 -1 -3 138.199 59.1745 5 7 -1 -2-9.18002 55.4643 2 7 -1 -2 223.056 63.1592 5 7 -1 -1-45.0396 57.9897 2 7 -1 -1 47.8226 57.9866 5 7 -1 0 63.7594 54.8869 2 7 -1 0 65.5664 62.4204 5 7 -1 1 53.8082 53.9151 2 7 -1 1-61.8910 64.0384 5 7 -1 2 52.4159 55.3062 2 7 -1 2 56.6603 58.1033 5 7 -1 3-47.3898 56.3558 5 7 -1 4 9.17856 55.6198 5 7 -1 5 85.2419 59.7043 5 7 -1 6 79.0097 56.5407 5 7 -1 7 100.715 51.8124 5 7 -1 8 58.9871 56.1834 5 7 -1 9-33.2322 61.6484 5 -7 0 11 33.1201 100.832 4 7 0 -11-186.644 73.6212 2 -7 0 10-174.589 91.2292 4 7 0 -10-26.5425 74.3002 2 7 0 -9 121.907 73.3796 2 -7 0 8-241.784 81.3595 4 7 0 -8 432.925 70.9785 2 7 0 -7 203.613 67.0373 2 7 0 -6-83.8169 65.1725 2 7 0 -5-99.8223 62.7059 2 7 0 -4-94.6835 57.2811 2 7 0 -3-55.1170 59.5550 2 7 0 -2 32.6767 55.3685 2 7 0 -2-45.3004 57.3698 5 7 0 -1 89.1996 56.0670 2 7 0 -1 210.939 56.5068 5 7 0 0 21.4125 50.7883 2 7 0 0 65.8674 61.3475 5 7 0 1 128.342 53.4609 2 7 0 1 83.0950 58.5694 5 7 0 2 210.219 55.3908 2 7 0 2 249.016 67.3173 5 7 0 3 237.287 52.4541 2 7 0 3 232.050 68.3836 5 7 0 4 301.906 65.1152 5 7 0 5 38.1122 63.6103 5 7 0 6-179.805 64.0089 5 7 0 7-44.5583 67.5326 5 7 0 8-108.611 72.0343 5 7 0 9 52.9705 72.9861 5 7 0 10 92.9909 75.2687 5 -7 -1 11-231.514 99.5976 4 -7 -1 10 127.451 89.8992 4 7 1 -10-119.492 71.8089 2 -7 -1 9-211.927 85.1260 4 7 1 -9 118.175 73.0830 2 7 1 -8 265.801 67.4221 2 7 1 -7 85.2352 63.3733 2 7 1 -6 85.0361 61.1953 2 7 1 -5 45.8398 60.7120 2 7 1 -4 26.0289 59.4063 2 7 1 -3-150.262 53.1098 2 7 1 -2-13.6966 54.6092 2 7 1 -1 80.8825 52.4222 2 7 1 0 121.459 55.3846 2 7 1 1 273.690 51.9899 2 7 1 1-21.9465 57.2609 5 7 1 2 143.990 52.4211 2 7 1 2 76.2635 60.8387 5 7 1 3 96.4529 51.7637 2 7 1 3 107.263 66.7025 5 7 1 4 132.984 65.4829 5 7 1 5 127.550 75.3092 5 7 1 6 268.341 75.5198 5 7 1 7 21.1680 76.3982 5 7 1 8-120.906 82.4074 5 7 1 9 187.957 82.4283 5 -7 -2 11 247.676 95.4966 4 -7 -2 10 167.174 92.3411 4 7 2 -9-199.343 66.0252 2 7 2 -8 41.8665 60.2639 2 7 2 -7 244.030 58.8681 2 7 2 -6 303.840 58.3257 2 7 2 -5 305.736 58.6887 2 7 2 -4-21.6840 57.1210 2 7 2 -2-98.6214 60.8639 2 7 2 -1 12.9785 53.2884 2 7 2 0 167.863 58.6938 2 7 2 1 8.07666 56.1481 2 7 2 2 169.777 54.0985 2 7 2 3 91.8631 55.3953 2 7 2 5 36.0646 79.5272 5 7 2 6 519.106 82.8037 5 7 3 -5 212.409 60.4221 2 7 3 -4 276.901 65.0718 2 7 3 -3-34.1116 65.2106 2 7 3 -2 36.8152 64.6380 2 7 3 0-60.9025 66.0036 2 7 3 2-143.360 60.8130 2 7 3 3-169.046 62.4849 2 7 3 4-29.2472 58.6983 2 8 0 0 56.7661 72.8864 2 8 0 1-146.830 74.3509 2 ; _shelx_hkl_checksum 91345 _shelx_res_file ; TITL HP1 IN P-1 shelx.res created by SHELXL-2018/3 at 18:36:47 on 24-Dec-2021 CELL 0.71073 6.23900 7.49600 17.81700 93.55000 92.94000 94.87000 ZERR 2 0.00100 0.00100 0.00300 0.02000 0.02000 0.02000 LATT 1 SFAC C H F N O UNIT 34 42 2 4 6 SHEL 18 0.83 SIZE 0.44 0.32 0.16 L.S. 14 CONF ACTA BOND $H htab HTAB N2 O1 HTAB N2 O2 EQIV $1 -x+1, -y+2, -z+1 HTAB N2 O3_$1 EQIV $2 -x+1, -y+1, -z+1 HTAB C8 O2_$2 HTAB C8 O3 EQIV $3 x-1, y, z HTAB C9 O3_$3 EQIV $4 x+1, y, z HTAB O3 O1_$4 HTAB O3 O2 DFIX 0.86 0.02 N2 H21 N2 H22 DFIX 0.82 0.02 O3 H31 O3 H32 OMIT -1 1 2 omit 0 -2 1 ! 2596.75 1418.46 7.64 0.258 3.70 omit -1 -3 2 ! 63.41 19.29 5.71 0.030 2.21 WGHT 0.071700 0.669400 FVAR 3.83716 N1 4 0.167343 0.691555 0.287537 11.00000 0.04642 0.04623 = 0.05333 0.00749 0.00607 -0.00285 N2 4 0.263745 0.757756 0.447417 11.00000 0.07175 0.04760 = 0.05473 0.00613 -0.00665 0.00643 H21 2 0.321182 0.736022 0.493194 11.00000 -1.20000 H22 2 0.222459 0.867109 0.453202 11.00000 -1.20000 C1 1 0.105427 0.711268 0.211599 11.00000 0.05776 0.04843 = 0.04845 0.00555 0.00451 0.00025 C2 1 -0.093704 0.644211 0.179624 11.00000 0.07947 0.09422 = 0.06043 0.01710 -0.00479 -0.02183 AFIX 43 H2 2 -0.193159 0.589826 0.210092 11.00000 -1.20000 AFIX 0 C3 1 -0.150985 0.654599 0.104469 11.00000 0.10448 0.11809 = 0.07028 0.01659 -0.02053 -0.03644 AFIX 43 H3 2 -0.285388 0.604546 0.084997 11.00000 -1.20000 AFIX 0 C4 1 -0.012234 0.737635 0.058463 11.00000 0.12889 0.11970 = 0.05568 0.01378 -0.00632 -0.01538 AFIX 43 H4 2 -0.049909 0.745192 0.007649 11.00000 -1.20000 AFIX 0 C5 1 0.182240 0.808968 0.088716 11.00000 0.11605 0.18492 = 0.05873 0.02888 0.00829 -0.04533 AFIX 43 H5 2 0.278723 0.865814 0.057892 11.00000 -1.20000 AFIX 0 C6 1 0.240941 0.799655 0.163741 11.00000 0.08801 0.14086 = 0.05799 0.02007 0.00314 -0.03875 AFIX 43 H6 2 0.373978 0.853592 0.182809 11.00000 -1.20000 AFIX 0 C7 1 0.362018 0.801879 0.317694 11.00000 0.04938 0.07235 = 0.05907 0.00949 0.00363 -0.00867 AFIX 23 H7A 2 0.332558 0.927034 0.320838 11.00000 -1.20000 H7B 2 0.476070 0.788623 0.283301 11.00000 -1.20000 AFIX 0 C8 1 0.437802 0.750858 0.394595 11.00000 0.05275 0.06537 = 0.06519 0.00306 -0.00160 0.00031 AFIX 23 H8A 2 0.484338 0.630572 0.390672 11.00000 -1.20000 H8B 2 0.560050 0.832523 0.413731 11.00000 -1.20000 AFIX 0 C9 1 0.069529 0.639766 0.416986 11.00000 0.06401 0.05628 = 0.05761 0.00695 0.00506 -0.00815 AFIX 23 H9A 2 -0.045974 0.649597 0.451027 11.00000 -1.20000 H9B 2 0.103679 0.515781 0.413417 11.00000 -1.20000 AFIX 0 C10 1 -0.003307 0.693343 0.340259 11.00000 0.04857 0.05795 = 0.06019 0.00597 0.00628 -0.00191 AFIX 23 H10A 2 -0.124568 0.611513 0.320378 11.00000 -1.20000 H10B 2 -0.051786 0.812879 0.345074 11.00000 -1.20000 AFIX 0 F1 3 0.531600 0.768363 0.945992 11.00000 0.17965 0.18662 = 0.06022 0.00426 -0.00200 0.00302 O1 5 0.144778 0.838283 0.618961 11.00000 0.09046 0.13989 = 0.11412 0.02883 -0.02691 0.03661 O2 5 0.418526 0.684862 0.591037 11.00000 0.09668 0.06940 = 0.06107 0.01008 -0.00456 0.00184 C11 1 0.367703 0.762807 0.719714 11.00000 0.04925 0.04059 = 0.06566 0.01255 0.00665 -0.00540 C12 1 0.551461 0.690007 0.745679 11.00000 0.06222 0.05626 = 0.06249 0.00565 -0.00111 0.00432 AFIX 43 H12 2 0.639144 0.638731 0.711219 11.00000 -1.20000 AFIX 0 C13 1 0.607381 0.691784 0.821372 11.00000 0.08217 0.08323 = 0.06728 0.01006 -0.00936 0.00924 AFIX 43 H13 2 0.731513 0.642435 0.838182 11.00000 -1.20000 AFIX 0 C14 1 0.478162 0.766848 0.871100 11.00000 0.10494 0.09832 = 0.05919 0.00360 -0.00151 -0.00465 C15 1 0.295865 0.842281 0.848557 11.00000 0.09666 0.09263 = 0.07917 0.00095 0.03051 0.00444 AFIX 43 H15 2 0.210580 0.894321 0.883627 11.00000 -1.20000 AFIX 0 C16 1 0.241553 0.839309 0.772546 11.00000 0.05674 0.06640 = 0.09573 0.01779 0.01222 0.00248 AFIX 43 H16 2 0.117563 0.889726 0.756336 11.00000 -1.20000 AFIX 0 C17 1 0.304935 0.761738 0.637524 11.00000 0.05582 0.04904 = 0.07576 0.02037 -0.00865 -0.01153 O3 5 0.782522 0.871760 0.542263 11.00000 0.07109 0.06509 = 0.08763 0.00393 -0.00880 0.01242 H31 2 0.897736 0.857007 0.565012 11.00000 -1.50000 H32 2 0.673663 0.829376 0.561712 11.00000 -1.50000 HKLF 4 REM HP1 IN P-1 REM wR2 = 0.2256, GooF = S = 1.104, Restrained GooF = 1.104 for all data REM R1 = 0.0898 for 1611 Fo > 4sig(Fo) and 0.1634 for all 3013 data REM 220 parameters refined using 4 restraints END WGHT 0.0716 0.6711 REM Instructions for potential hydrogen bonds HTAB N2 O1 HTAB N2 O2 HTAB N2 O3_$1 HTAB C8 O2_$2 HTAB C8 O3 HTAB C9 O3_$3 HTAB O3 O1_$4 HTAB O3 O2 REM Highest difference peak 0.273, deepest hole -0.196, 1-sigma level 0.052 Q1 1 0.4751 0.6833 0.6622 11.00000 0.05 0.27 Q2 1 0.2444 0.7559 0.5745 11.00000 0.05 0.26 Q3 1 0.1880 0.8341 0.6987 11.00000 0.05 0.26 Q4 1 0.3809 0.8416 0.9198 11.00000 0.05 0.25 Q5 1 0.4213 0.7557 0.7916 11.00000 0.05 0.24 Q6 1 0.6718 0.6929 0.8917 11.00000 0.05 0.22 Q7 1 0.2116 0.6673 0.1523 11.00000 0.05 0.21 Q8 1 0.1162 0.8407 0.5563 11.00000 0.05 0.19 Q9 1 0.0419 0.8529 0.6018 11.00000 0.05 0.18 Q10 1 0.1598 0.7011 0.3481 11.00000 0.05 0.18 Q11 1 0.3524 0.7638 0.6777 11.00000 0.05 0.18 Q12 1 0.3307 0.7807 0.7437 11.00000 0.05 0.17 Q13 1 0.3109 0.8913 0.7721 11.00000 0.05 0.17 Q14 1 0.2883 0.7804 0.6640 11.00000 0.05 0.17 Q15 1 0.4082 0.6845 0.5367 11.00000 0.05 0.17 Q16 1 0.4262 0.7366 0.1648 11.00000 0.05 0.16 Q17 1 0.8323 0.8580 0.6124 11.00000 0.05 0.16 Q18 1 0.5491 0.7262 0.9392 11.00000 0.05 0.15 Q19 1 0.1605 0.6803 0.0775 11.00000 0.05 0.15 Q20 1 0.1915 0.8551 0.8113 11.00000 0.05 0.15 ; _shelx_res_checksum 23153 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 N N1 0.1673(5) 0.6916(4) 0.28754(18) 0.0488(8) Uani d 1 . . N N2 0.2637(6) 0.7578(5) 0.4474(2) 0.0582(10) Uani d 1 . . H H21 0.321(6) 0.736(6) 0.4932(14) 0.070 Uiso d 1 . . H H22 0.222(6) 0.867(3) 0.453(2) 0.070 Uiso d 1 . . C C1 0.1054(6) 0.7113(5) 0.2116(2) 0.0517(10) Uani d 1 . . C C2 -0.0937(8) 0.6442(7) 0.1796(3) 0.0795(15) Uani d 1 . . H H2 -0.193159 0.589826 0.210092 0.095 Uiso calc 1 . . C C3 -0.1510(9) 0.6546(8) 0.1045(3) 0.1007(19) Uani d 1 . . H H3 -0.285388 0.604546 0.084997 0.121 Uiso calc 1 . . C C4 -0.0122(11) 0.7376(9) 0.0585(3) 0.1030(19) Uani d 1 . . H H4 -0.049909 0.745192 0.007649 0.124 Uiso calc 1 . . C C5 0.1822(10) 0.8090(10) 0.0887(3) 0.122(3) Uani d 1 . . H H5 0.278723 0.865814 0.057892 0.147 Uiso calc 1 . . C C6 0.2409(9) 0.7997(8) 0.1637(3) 0.0979(19) Uani d 1 . . H H6 0.373978 0.853592 0.182809 0.117 Uiso calc 1 . . C C7 0.3620(6) 0.8019(6) 0.3177(2) 0.0608(11) Uani d 1 . . H H7A 0.332558 0.927034 0.320838 0.073 Uiso calc 1 . . H H7B 0.476070 0.788623 0.283301 0.073 Uiso calc 1 . . C C8 0.4378(7) 0.7509(6) 0.3946(2) 0.0616(12) Uani d 1 . . H H8A 0.484338 0.630572 0.390672 0.074 Uiso calc 1 . . H H8B 0.560050 0.832523 0.413731 0.074 Uiso calc 1 . . C C9 0.0695(7) 0.6398(6) 0.4170(2) 0.0599(11) Uani d 1 . . H H9A -0.045974 0.649597 0.451027 0.072 Uiso calc 1 . . H H9B 0.103679 0.515781 0.413417 0.072 Uiso calc 1 . . C C10 -0.0033(6) 0.6933(6) 0.3403(2) 0.0558(11) Uani d 1 . . H H10A -0.124568 0.611513 0.320378 0.067 Uiso calc 1 . . H H10B -0.051786 0.812879 0.345074 0.067 Uiso calc 1 . . F F1 0.5316(7) 0.7684(6) 0.94599(18) 0.1434(15) Uani d 1 . . O O1 0.1448(6) 0.8383(6) 0.6190(2) 0.1136(14) Uani d 1 . . O O2 0.4185(6) 0.6849(4) 0.59104(18) 0.0761(10) Uani d 1 . . C C11 0.3677(6) 0.7628(5) 0.7197(2) 0.0519(10) Uani d 1 . . C C12 0.5515(7) 0.6900(6) 0.7457(2) 0.0605(11) Uani d 1 . . H H12 0.639144 0.638731 0.711219 0.073 Uiso calc 1 . . C C13 0.6074(8) 0.6918(7) 0.8214(3) 0.0777(14) Uani d 1 . . H H13 0.731513 0.642435 0.838182 0.093 Uiso calc 1 . . C C14 0.4782(10) 0.7668(8) 0.8711(3) 0.0885(16) Uani d 1 . . C C15 0.2959(10) 0.8423(8) 0.8486(3) 0.0890(16) Uani d 1 . . H H15 0.210580 0.894321 0.883627 0.107 Uiso calc 1 . . C C16 0.2416(7) 0.8393(6) 0.7725(3) 0.0723(13) Uani d 1 . . H H16 0.117563 0.889726 0.756336 0.087 Uiso calc 1 . . C C17 0.3049(7) 0.7617(6) 0.6375(3) 0.0609(12) Uani d 1 . . O O3 0.7825(5) 0.8718(5) 0.5423(2) 0.0747(10) Uani d 1 . . H H31 0.898(5) 0.857(8) 0.565(3) 0.112 Uiso d 1 . . H H32 0.674(6) 0.829(8) 0.562(3) 0.112 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 N1 0.0464(19) 0.0462(19) 0.053(2) -0.0029(14) 0.0061(15) 0.0075(14) N2 0.072(2) 0.048(2) 0.055(2) 0.0064(18) -0.0066(19) 0.0061(17) C1 0.058(3) 0.048(2) 0.048(3) 0.0003(19) 0.005(2) 0.0056(18) C2 0.079(3) 0.094(4) 0.060(3) -0.022(3) -0.005(3) 0.017(3) C3 0.104(4) 0.118(5) 0.070(4) -0.036(4) -0.021(3) 0.017(3) C4 0.129(5) 0.120(5) 0.056(3) -0.015(4) -0.006(3) 0.014(3) C5 0.116(5) 0.185(7) 0.059(4) -0.045(5) 0.008(3) 0.029(4) C6 0.088(4) 0.141(5) 0.058(3) -0.039(4) 0.003(3) 0.020(3) C7 0.049(2) 0.072(3) 0.059(3) -0.009(2) 0.004(2) 0.009(2) C8 0.053(3) 0.065(3) 0.065(3) 0.000(2) -0.002(2) 0.003(2) C9 0.064(3) 0.056(3) 0.058(3) -0.008(2) 0.005(2) 0.007(2) C10 0.049(2) 0.058(3) 0.060(3) -0.0019(19) 0.006(2) 0.006(2) F1 0.180(4) 0.187(4) 0.060(2) 0.003(3) -0.002(2) 0.004(2) O1 0.090(3) 0.140(4) 0.114(3) 0.037(3) -0.027(2) 0.029(3) O2 0.097(2) 0.069(2) 0.061(2) 0.0018(18) -0.0046(18) 0.0101(16) C11 0.049(2) 0.041(2) 0.066(3) -0.0054(18) 0.007(2) 0.0126(19) C12 0.062(3) 0.056(3) 0.062(3) 0.004(2) -0.001(2) 0.006(2) C13 0.082(3) 0.083(4) 0.067(3) 0.009(3) -0.009(3) 0.010(3) C14 0.105(4) 0.098(4) 0.059(3) -0.005(3) -0.002(3) 0.004(3) C15 0.097(4) 0.093(4) 0.079(4) 0.004(3) 0.031(3) 0.001(3) C16 0.057(3) 0.066(3) 0.096(4) 0.002(2) 0.012(3) 0.018(3) C17 0.056(3) 0.049(3) 0.076(3) -0.012(2) -0.009(2) 0.020(2) O3 0.071(2) 0.065(2) 0.088(3) 0.0124(18) -0.0088(18) 0.0039(17) 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' F F 0.0171 0.0103 '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 C1 N1 C10 . . 116.2(3) ? C1 N1 C7 . . 115.9(3) ? C10 N1 C7 . . 111.5(3) ? C8 N2 C9 . . 110.3(3) ? C8 N2 H21 . . 107(3) ? C9 N2 H21 . . 117(3) ? C8 N2 H22 . . 111(3) ? C9 N2 H22 . . 106(3) ? H21 N2 H22 . . 105(4) ? C2 C1 C6 . . 115.5(4) ? C2 C1 N1 . . 122.4(4) ? C6 C1 N1 . . 122.2(4) ? C3 C2 C1 . . 122.7(5) ? C3 C2 H2 . . 118.7 ? C1 C2 H2 . . 118.7 ? C4 C3 C2 . . 120.5(5) ? C4 C3 H3 . . 119.8 ? C2 C3 H3 . . 119.8 ? C5 C4 C3 . . 118.2(5) ? C5 C4 H4 . . 120.9 ? C3 C4 H4 . . 120.9 ? C4 C5 C6 . . 121.8(5) ? C4 C5 H5 . . 119.1 ? C6 C5 H5 . . 119.1 ? C5 C6 C1 . . 121.3(5) ? C5 C6 H6 . . 119.4 ? C1 C6 H6 . . 119.4 ? N1 C7 C8 . . 112.4(3) ? N1 C7 H7A . . 109.1 ? C8 C7 H7A . . 109.1 ? N1 C7 H7B . . 109.1 ? C8 C7 H7B . . 109.1 ? H7A C7 H7B . . 107.9 ? N2 C8 C7 . . 110.8(3) ? N2 C8 H8A . . 109.5 ? C7 C8 H8A . . 109.5 ? N2 C8 H8B . . 109.5 ? C7 C8 H8B . . 109.5 ? H8A C8 H8B . . 108.1 ? N2 C9 C10 . . 110.4(3) ? N2 C9 H9A . . 109.6 ? C10 C9 H9A . . 109.6 ? N2 C9 H9B . . 109.6 ? C10 C9 H9B . . 109.6 ? H9A C9 H9B . . 108.1 ? N1 C10 C9 . . 112.3(3) ? N1 C10 H10A . . 109.1 ? C9 C10 H10A . . 109.1 ? N1 C10 H10B . . 109.1 ? C9 C10 H10B . . 109.1 ? H10A C10 H10B . . 107.9 ? C12 C11 C16 . . 117.8(4) ? C12 C11 C17 . . 121.9(4) ? C16 C11 C17 . . 120.2(4) ? C13 C12 C11 . . 121.4(4) ? C13 C12 H12 . . 119.3 ? C11 C12 H12 . . 119.3 ? C14 C13 C12 . . 118.8(5) ? C14 C13 H13 . . 120.6 ? C12 C13 H13 . . 120.6 ? C13 C14 F1 . . 119.2(6) ? C13 C14 C15 . . 122.3(5) ? F1 C14 C15 . . 118.5(6) ? C14 C15 C16 . . 118.3(5) ? C14 C15 H15 . . 120.9 ? C16 C15 H15 . . 120.9 ? C15 C16 C11 . . 121.4(5) ? C15 C16 H16 . . 119.3 ? C11 C16 H16 . . 119.3 ? O1 C17 O2 . . 123.6(5) ? O1 C17 C11 . . 117.7(5) ? O2 C17 C11 . . 118.7(4) ? H31 O3 H32 . . 115(6) ? 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 N1 C1 . 1.408(5) ? N1 C10 . 1.456(5) ? N1 C7 . 1.468(5) ? N2 C8 . 1.475(5) ? N2 C9 . 1.495(5) ? N2 H21 . 0.904(19) ? N2 H22 . 0.881(19) ? C1 C2 . 1.381(6) ? C1 C6 . 1.389(6) ? C2 C3 . 1.377(6) ? C2 H2 . 0.9300 ? C3 C4 . 1.361(8) ? C3 H3 . 0.9300 ? C4 C5 . 1.355(8) ? C4 H4 . 0.9300 ? C5 C6 . 1.375(7) ? C5 H5 . 0.9300 ? C6 H6 . 0.9300 ? C7 C8 . 1.509(5) ? C7 H7A . 0.9700 ? C7 H7B . 0.9700 ? C8 H8A . 0.9700 ? C8 H8B . 0.9700 ? C9 C10 . 1.507(5) ? C9 H9A . 0.9700 ? C9 H9B . 0.9700 ? C10 H10A . 0.9700 ? C10 H10B . 0.9700 ? F1 C14 . 1.358(6) ? O1 C17 . 1.235(5) ? O2 C17 . 1.261(5) ? C11 C12 . 1.382(5) ? C11 C16 . 1.386(6) ? C11 C17 . 1.496(6) ? C12 C13 . 1.375(6) ? C12 H12 . 0.9300 ? C13 C14 . 1.356(7) ? C13 H13 . 0.9300 ? C14 C15 . 1.366(7) ? C15 C16 . 1.377(7) ? C15 H15 . 0.9300 ? C16 H16 . 0.9300 ? O3 H31 . 0.83(2) ? O3 H32 . 0.83(2) ? 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 N2 H21 O1 . 0.904(19) 2.65(4) 3.215(6) 122(3) yes N2 H21 O2 . 0.904(19) 1.89(2) 2.791(5) 175(4) yes N2 H22 O3 2_676 0.881(19) 1.96(2) 2.812(5) 163(4) yes C8 H8A O2 2_666 0.97 2.53 3.481(6) 167.8 yes C8 H8B O3 . 0.97 2.60 3.341(5) 133.0 yes C9 H9A O3 1_455 0.97 2.59 3.416(6) 143.2 yes O3 H31 O1 1_655 0.83(2) 1.79(2) 2.619(5) 176(6) yes O3 H32 O2 . 0.83(2) 1.96(2) 2.773(5) 167(6) 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 C10 N1 C1 C2 . . . . -33.4(6) ? C7 N1 C1 C2 . . . . -167.2(4) ? C10 N1 C1 C6 . . . . 146.6(5) ? C7 N1 C1 C6 . . . . 12.8(6) ? C6 C1 C2 C3 . . . . 3.5(8) ? N1 C1 C2 C3 . . . . -176.4(5) ? C1 C2 C3 C4 . . . . -1.9(9) ? C2 C3 C4 C5 . . . . 0.0(10) ? C3 C4 C5 C6 . . . . -0.2(11) ? C4 C5 C6 C1 . . . . 2.1(11) ? C2 C1 C6 C5 . . . . -3.6(8) ? N1 C1 C6 C5 . . . . 176.4(6) ? C1 N1 C7 C8 . . . . -170.5(3) ? C10 N1 C7 C8 . . . . 53.5(5) ? C9 N2 C8 C7 . . . . 56.3(4) ? N1 C7 C8 N2 . . . . -55.1(5) ? C8 N2 C9 C10 . . . . -56.6(4) ? C1 N1 C10 C9 . . . . 170.1(3) ? C7 N1 C10 C9 . . . . -54.1(4) ? N2 C9 C10 N1 . . . . 55.9(4) ? C16 C11 C12 C13 . . . . 0.5(6) ? C17 C11 C12 C13 . . . . -180.0(4) ? C11 C12 C13 C14 . . . . 0.0(7) ? C12 C13 C14 F1 . . . . 179.7(4) ? C12 C13 C14 C15 . . . . -0.7(8) ? C13 C14 C15 C16 . . . . 0.8(9) ? F1 C14 C15 C16 . . . . -179.6(4) ? C14 C15 C16 C11 . . . . -0.3(8) ? C12 C11 C16 C15 . . . . -0.4(6) ? C17 C11 C16 C15 . . . . -179.9(4) ? C12 C11 C17 O1 . . . . -176.1(4) ? C16 C11 C17 O1 . . . . 3.4(6) ? C12 C11 C17 O2 . . . . 3.2(6) ? C16 C11 C17 O2 . . . . -177.3(4) ?