#------------------------------------------------------------------------------ #$Date: 2018-01-10 07:45:33 +0200 (Wed, 10 Jan 2018) $ #$Revision: 205019 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/99/7229936.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7229936 loop_ _publ_author_name 'Yang, Wei' 'Lu, Huanchang' 'Liao, Longyu' 'Fan, Guijuan' 'Ma, Qing' 'Huang, Jinglun' _publ_section_title ; Synthesis, and single crystal structure of fully-substituted polynitrobenzene derivatives for high-energy materials ; _journal_issue 4 _journal_name_full 'RSC Advances' _journal_page_first 2203 _journal_paper_doi 10.1039/C7RA13346D _journal_volume 8 _journal_year 2018 _chemical_formula_sum 'C16 H16 N16 O8' _chemical_formula_weight 560.45 _chemical_name_systematic ; ? ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2013 _audit_update_record ; 2017-05-25 deposited with the CCDC. 2018-01-03 downloaded from the CCDC. ; _cell_angle_alpha 87.286(4) _cell_angle_beta 87.725(3) _cell_angle_gamma 89.891(3) _cell_formula_units_Z 2 _cell_length_a 7.4815(11) _cell_length_b 9.2466(13) _cell_length_c 16.151(3) _cell_measurement_reflns_used 1742 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 54.567 _cell_measurement_theta_min 5.054 _cell_volume 1115.2(3) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_structure_solution 'Bruker SHELXTL' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0212 _diffrn_reflns_av_unetI/netI 0.0414 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 6451 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.498 _diffrn_reflns_theta_min 2.489 _exptl_absorpt_coefficient_mu 0.138 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6290 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.669 _exptl_crystal_description prismatic _exptl_crystal_F_000 576 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.170 _exptl_crystal_size_min 0.110 _refine_diff_density_max 0.247 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.047 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 361 _refine_ls_number_reflns 4134 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.034 _refine_ls_R_factor_all 0.0647 _refine_ls_R_factor_gt 0.0486 _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^)+(0.0698P)^2^+0.1534P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1219 _refine_ls_wR_factor_ref 0.1331 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3198 _reflns_number_total 4134 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ra13346d2.cif _cod_data_source_block cd16258 _cod_database_code 7229936 _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 0.973 _shelx_estimated_absorpt_t_max 0.985 _shelxl_version_number 2013-4 _shelx_res_file ; TITL cd16258 in P-1 CELL 0.71073 7.4815 9.2466 16.1511 87.286 87.725 89.891 ZERR 2.00 0.0011 0.0013 0.0025 0.004 0.003 0.003 LATT 1 SFAC C H N O UNIT 32 32 32 16 OMIT 0 0 1 OMIT 1 4 1 OMIT 2 2 6 OMIT 2 3 0 OMIT -2 -2 3 OMIT -3.00 51.00 L.S. 10 ACTA BOND $H FMAP 2 PLAN 20 HTAB C10 O8_$1 HTAB C9 O1_$5 HTAB C2 O4_$1 HTAB C2 O3_$1 HTAB C2 N7_$1 HTAB N16 O8 HTAB N16 N9_$5 EQIV $5 -x, -y, -z HTAB N14 O7 HTAB N14 O6 HTAB N14 N1_$3 HTAB N12 O5 HTAB N12 O3_$4 EQIV $4 x-1, y-1, z HTAB N8 O4 HTAB N8 O6_$3 EQIV $3 -x, -y+1, -z+1 HTAB N6 O3 HTAB N6 O2_$2 EQIV $2 -x+1, -y+1, -z HTAB N6 O2 HTAB N4 O1 HTAB N4 O7_$1 EQIV $1 x-1, y, z conf mpla c1 c2 n1 n2 n3 mpla c3 > c8 mpla c11 > c16 mpla n9 n10 n11 c9 c10 size 0.20 0.17 0.11 wpdb -1 WGHT 0.069800 0.153400 FVAR 0.15448 MOLE 1 N1 3 -0.344142 0.601928 0.418627 11.00000 0.03618 0.06277 = 0.04472 -0.00986 0.00781 -0.00890 N2 3 -0.101518 0.461703 0.397925 11.00000 0.05090 0.04392 = 0.04287 0.00400 0.01053 -0.00423 N3 3 -0.095305 0.581037 0.345222 11.00000 0.02983 0.03207 = 0.02882 -0.00317 0.00449 -0.00577 N4 3 -0.103399 0.458457 0.197340 11.00000 0.04469 0.05803 = 0.04986 -0.02548 0.01384 -0.02582 AFIX 93 H4A 2 -0.188238 0.450319 0.234780 11.00000 -1.20000 H4B 2 -0.111563 0.415586 0.151536 11.00000 -1.20000 AFIX 0 N5 3 0.185945 0.479443 0.077207 11.00000 0.04207 0.05046 = 0.03890 -0.01750 0.00712 -0.00780 N6 3 0.461831 0.673314 0.109360 11.00000 0.04659 0.09597 = 0.05170 -0.03578 0.02373 -0.03503 AFIX 93 H6A 2 0.463429 0.628003 0.064047 11.00000 -1.20000 H6B 2 0.546954 0.732085 0.118583 11.00000 -1.20000 AFIX 0 N7 3 0.453336 0.831952 0.254209 11.00000 0.02905 0.04459 = 0.03601 -0.00348 -0.00148 -0.01047 N8 3 0.176322 0.763983 0.374630 11.00000 0.03969 0.06087 = 0.03350 -0.01720 0.00666 -0.01978 AFIX 93 H8A 2 0.089308 0.745325 0.409892 11.00000 -1.20000 H8B 2 0.258878 0.823570 0.386122 11.00000 -1.20000 AFIX 0 MOLE 2 N9 3 -0.190412 -0.033029 0.045608 11.00000 0.03502 0.05681 = 0.03067 -0.01292 -0.00137 -0.01314 N10 3 -0.003912 -0.129817 0.138939 11.00000 0.04830 0.03509 = 0.04104 -0.01215 -0.00236 -0.00482 N11 3 -0.021218 0.016244 0.147035 11.00000 0.03228 0.03132 = 0.02714 -0.00942 -0.00083 -0.00694 N12 3 -0.179281 0.042644 0.299257 11.00000 0.03848 0.05665 = 0.03412 -0.01446 0.00524 -0.02245 AFIX 93 H12A 2 -0.230951 0.003234 0.259379 11.00000 -1.20000 H12B 2 -0.233706 0.047113 0.346978 11.00000 -1.20000 AFIX 0 N13 3 0.001359 0.161154 0.432021 11.00000 0.04217 0.03943 = 0.02967 -0.00697 0.00580 -0.01141 N14 3 0.332867 0.295001 0.390556 11.00000 0.04798 0.09786 = 0.03469 -0.03317 0.00931 -0.03663 AFIX 93 H14A 2 0.285674 0.298007 0.439872 11.00000 -1.20000 H14B 2 0.434773 0.335372 0.378789 11.00000 -1.20000 AFIX 0 N15 3 0.487119 0.292574 0.229609 11.00000 0.03331 0.05488 = 0.03538 -0.01709 0.00538 -0.01556 N16 3 0.317680 0.115885 0.116016 11.00000 0.03286 0.06707 = 0.02961 -0.02117 0.00346 -0.01335 AFIX 93 H16A 2 0.261485 0.067797 0.080904 11.00000 -1.20000 H16B 2 0.423566 0.148083 0.103489 11.00000 -1.20000 AFIX 0 MOLE 1 O1 4 0.064820 0.393261 0.064971 11.00000 0.06408 0.05630 = 0.04943 -0.02661 0.00655 -0.02366 O2 4 0.305531 0.497782 0.022189 11.00000 0.05753 0.12340 = 0.05916 -0.05436 0.02885 -0.03346 O3 4 0.581648 0.855429 0.203104 11.00000 0.04237 0.08392 = 0.04574 -0.01226 0.01050 -0.03547 O4 4 0.447209 0.903753 0.317211 11.00000 0.04307 0.05317 = 0.04934 -0.02109 0.00307 -0.01722 MOLE 2 O5 4 -0.155585 0.123881 0.446334 11.00000 0.04918 0.07351 = 0.04146 -0.01794 0.01741 -0.02985 O6 4 0.090257 0.200685 0.490531 11.00000 0.05289 0.07574 = 0.02640 -0.01345 0.00049 -0.01650 O7 4 0.555393 0.375259 0.278183 11.00000 0.05837 0.10611 = 0.05284 -0.04357 0.01691 -0.05198 O8 4 0.564976 0.278628 0.161396 11.00000 0.04826 0.09991 = 0.04470 -0.03464 0.01949 -0.03489 MOLE 1 C1 1 -0.253455 0.481375 0.439400 11.00000 0.04901 0.05095 = 0.03793 -0.00148 0.00968 -0.01288 AFIX 43 H1A 2 -0.295702 0.415405 0.480823 11.00000 -1.20000 AFIX 0 C2 1 -0.239969 0.661093 0.359526 11.00000 0.03341 0.04645 = 0.04446 0.00137 0.00031 -0.00130 AFIX 43 H2A 2 -0.264125 0.748290 0.331071 11.00000 -1.20000 AFIX 0 C3 1 0.048604 0.604929 0.285088 11.00000 0.02661 0.03568 = 0.02882 -0.00338 0.00504 -0.00678 C4 1 0.039656 0.536917 0.210205 11.00000 0.03197 0.03041 = 0.03271 -0.00509 0.00184 -0.00576 C5 1 0.186073 0.555374 0.150478 11.00000 0.03120 0.03796 = 0.03179 -0.01105 0.00333 -0.00473 C6 1 0.328939 0.652688 0.164662 11.00000 0.02987 0.04613 = 0.03517 -0.00767 0.00560 -0.00450 C7 1 0.324076 0.728222 0.240694 11.00000 0.02655 0.03727 = 0.02878 -0.00480 -0.00009 -0.00794 C8 1 0.183189 0.700919 0.302589 11.00000 0.02932 0.03670 = 0.02815 -0.00548 -0.00112 -0.00210 MOLE 2 C9 1 -0.107718 -0.151718 0.077891 11.00000 0.04387 0.04776 = 0.03606 -0.01799 0.00456 -0.01747 AFIX 43 H9 2 -0.123921 -0.243182 0.057788 11.00000 -1.20000 AFIX 0 C10 1 -0.132466 0.069087 0.091007 11.00000 0.03319 0.04281 = 0.02992 -0.00562 -0.00050 -0.00430 AFIX 43 H10 2 -0.164859 0.166043 0.084894 11.00000 -1.20000 AFIX 0 C11 1 0.070252 0.088212 0.209360 11.00000 0.03098 0.03214 = 0.02453 -0.00858 -0.00339 -0.00517 C12 1 -0.015804 0.096484 0.287172 11.00000 0.03015 0.02741 = 0.03330 -0.00426 -0.00092 -0.00623 C13 1 0.079560 0.160750 0.351274 11.00000 0.03568 0.03427 = 0.02298 -0.00898 0.00389 -0.00740 C14 1 0.249298 0.228749 0.333204 11.00000 0.03191 0.04024 = 0.02850 -0.01142 0.00002 -0.00669 C15 1 0.326526 0.221860 0.250854 11.00000 0.02726 0.03753 = 0.02918 -0.01063 0.00187 -0.00802 C16 1 0.241114 0.140370 0.189420 11.00000 0.03150 0.03265 = 0.02486 -0.00633 -0.00201 -0.00274 HKLF 4 REM cd16258 in P-1 REM R1 = 0.0486 for 3198 Fo > 4sig(Fo) and 0.0647 for all 4134 data REM 361 parameters refined using 0 restraints END WGHT 0.0697 0.1639 REM Highest difference peak 0.247, deepest hole -0.219, 1-sigma level 0.047 Q1 1 0.6006 0.2879 0.2870 11.00000 0.05 0.25 Q2 1 0.0750 0.5487 0.2611 11.00000 0.05 0.24 Q3 1 0.2463 0.2704 0.2788 11.00000 0.05 0.23 Q4 1 0.2891 0.1752 0.2269 11.00000 0.05 0.23 Q5 1 0.0224 0.2005 0.3778 11.00000 0.05 0.23 Q6 1 0.2920 0.6874 0.2794 11.00000 0.05 0.22 Q7 1 0.3624 0.7830 0.2460 11.00000 0.05 0.22 Q8 1 0.1387 0.2285 0.3396 11.00000 0.05 0.21 Q9 1 0.0558 0.0560 0.2597 11.00000 0.05 0.21 Q10 1 0.5270 0.3959 0.2544 11.00000 0.05 0.21 Q11 1 0.1302 0.1413 0.1991 11.00000 0.05 0.20 Q12 1 0.1385 0.6185 0.2996 11.00000 0.05 0.20 Q13 1 0.0299 0.1414 0.3198 11.00000 0.05 0.20 Q14 1 0.3324 0.4546 0.0631 11.00000 0.05 0.19 Q15 1 0.0972 0.6627 0.2854 11.00000 0.05 0.19 Q16 1 0.1356 0.5667 0.1036 11.00000 0.05 0.19 Q17 1 0.3639 0.7109 0.1195 11.00000 0.05 0.19 Q18 1 0.3475 0.6686 0.2177 11.00000 0.05 0.19 Q19 1 0.2236 0.4762 0.1367 11.00000 0.05 0.19 Q20 1 0.2402 0.7288 0.2577 11.00000 0.05 0.19 ; _shelx_res_checksum 23419 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp N1 N -0.3441(3) 0.6019(2) 0.41863(12) 0.0479(5) Uani 1 1 d . . N2 N -0.1015(3) 0.4617(2) 0.39793(12) 0.0464(5) Uani 1 1 d . . N3 N -0.0953(2) 0.58104(18) 0.34522(10) 0.0303(4) Uani 1 1 d . . N4 N -0.1034(3) 0.4585(2) 0.19734(13) 0.0505(6) Uani 1 1 d . . H4A H -0.1882 0.4503 0.2348 0.061 Uiso 1 1 calc R U H4B H -0.1116 0.4156 0.1515 0.061 Uiso 1 1 calc R U N5 N 0.1859(3) 0.4794(2) 0.07721(12) 0.0435(5) Uani 1 1 d . . N6 N 0.4618(3) 0.6733(3) 0.10936(14) 0.0644(7) Uani 1 1 d . . H6A H 0.4634 0.6280 0.0640 0.077 Uiso 1 1 calc R U H6B H 0.5470 0.7321 0.1186 0.077 Uiso 1 1 calc R U N7 N 0.4533(2) 0.8320(2) 0.25421(11) 0.0365(4) Uani 1 1 d . . N8 N 0.1763(3) 0.7640(2) 0.37463(11) 0.0444(5) Uani 1 1 d . . H8A H 0.0893 0.7453 0.4099 0.053 Uiso 1 1 calc R U H8B H 0.2589 0.8236 0.3861 0.053 Uiso 1 1 calc R U N9 N -0.1904(2) -0.0330(2) 0.04561(11) 0.0405(5) Uani 1 1 d . . N10 N -0.0039(3) -0.1298(2) 0.13894(12) 0.0411(5) Uani 1 1 d . . N11 N -0.0212(2) 0.01624(18) 0.14704(10) 0.0300(4) Uani 1 1 d . . N12 N -0.1793(2) 0.0426(2) 0.29926(12) 0.0428(5) Uani 1 1 d . . H12A H -0.2310 0.0032 0.2594 0.051 Uiso 1 1 calc R U H12B H -0.2337 0.0471 0.3470 0.051 Uiso 1 1 calc R U N13 N 0.0014(3) 0.1612(2) 0.43202(11) 0.0371(4) Uani 1 1 d . . N14 N 0.3329(3) 0.2950(3) 0.39056(12) 0.0595(7) Uani 1 1 d . . H14A H 0.2857 0.2980 0.4399 0.071 Uiso 1 1 calc R U H14B H 0.4348 0.3354 0.3788 0.071 Uiso 1 1 calc R U N15 N 0.4871(2) 0.2926(2) 0.22961(11) 0.0409(5) Uani 1 1 d . . N16 N 0.3177(2) 0.1159(2) 0.11602(11) 0.0427(5) Uani 1 1 d . . H16A H 0.2615 0.0678 0.0809 0.051 Uiso 1 1 calc R U H16B H 0.4236 0.1481 0.1035 0.051 Uiso 1 1 calc R U O1 O 0.0648(2) 0.39326(19) 0.06497(11) 0.0560(5) Uani 1 1 d . . O2 O 0.3055(3) 0.4978(3) 0.02219(12) 0.0792(7) Uani 1 1 d . . O3 O 0.5816(2) 0.8554(2) 0.20310(10) 0.0573(5) Uani 1 1 d . . O4 O 0.4472(2) 0.90375(18) 0.31721(10) 0.0480(4) Uani 1 1 d . . O5 O -0.1556(2) 0.12388(19) 0.44633(10) 0.0547(5) Uani 1 1 d . . O6 O 0.0903(2) 0.2007(2) 0.49053(9) 0.0514(5) Uani 1 1 d . . O7 O 0.5554(2) 0.3753(2) 0.27818(11) 0.0716(7) Uani 1 1 d . . O8 O 0.5650(2) 0.2786(2) 0.16140(11) 0.0638(6) Uani 1 1 d . . C1 C -0.2535(3) 0.4814(3) 0.43940(15) 0.0463(6) Uani 1 1 d . . H1A H -0.2957 0.4154 0.4808 0.056 Uiso 1 1 calc R U C2 C -0.2400(3) 0.6611(3) 0.35953(14) 0.0416(6) Uani 1 1 d . . H2A H -0.2641 0.7483 0.3311 0.050 Uiso 1 1 calc R U C3 C 0.0486(3) 0.6049(2) 0.28509(12) 0.0305(5) Uani 1 1 d . . C4 C 0.0397(3) 0.5369(2) 0.21021(13) 0.0317(5) Uani 1 1 d . . C5 C 0.1861(3) 0.5554(2) 0.15048(13) 0.0335(5) Uani 1 1 d . . C6 C 0.3289(3) 0.6527(2) 0.16466(13) 0.0371(5) Uani 1 1 d . . C7 C 0.3241(3) 0.7282(2) 0.24069(12) 0.0308(5) Uani 1 1 d . . C8 C 0.1832(3) 0.7009(2) 0.30259(12) 0.0313(5) Uani 1 1 d . . C9 C -0.1077(3) -0.1517(3) 0.07789(14) 0.0422(6) Uani 1 1 d . . H9 H -0.1239 -0.2432 0.0578 0.051 Uiso 1 1 calc R U C10 C -0.1325(3) 0.0691(2) 0.09101(13) 0.0352(5) Uani 1 1 d . . H10 H -0.1649 0.1660 0.0849 0.042 Uiso 1 1 calc R U C11 C 0.0703(3) 0.0882(2) 0.20936(12) 0.0289(5) Uani 1 1 d . . C12 C -0.0158(3) 0.0965(2) 0.28717(12) 0.0302(5) Uani 1 1 d . . C13 C 0.0796(3) 0.1607(2) 0.35127(12) 0.0309(5) Uani 1 1 d . . C14 C 0.2493(3) 0.2287(2) 0.33320(13) 0.0333(5) Uani 1 1 d . . C15 C 0.3265(3) 0.2219(2) 0.25085(12) 0.0311(5) Uani 1 1 d . . C16 C 0.2411(3) 0.1404(2) 0.18942(12) 0.0295(5) Uani 1 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0362(11) 0.0628(14) 0.0447(12) -0.0099(10) 0.0078(9) -0.0089(10) N2 0.0509(13) 0.0439(12) 0.0429(12) 0.0040(9) 0.0105(9) -0.0042(9) N3 0.0298(10) 0.0321(10) 0.0288(9) -0.0032(7) 0.0045(7) -0.0058(7) N4 0.0447(12) 0.0580(13) 0.0499(12) -0.0255(10) 0.0138(9) -0.0258(10) N5 0.0421(11) 0.0505(12) 0.0389(11) -0.0175(9) 0.0071(9) -0.0078(9) N6 0.0466(13) 0.0960(18) 0.0517(13) -0.0358(12) 0.0237(10) -0.0350(12) N7 0.0291(10) 0.0446(11) 0.0360(10) -0.0035(8) -0.0015(8) -0.0105(8) N8 0.0397(11) 0.0609(13) 0.0335(11) -0.0172(9) 0.0067(8) -0.0198(9) N9 0.0350(10) 0.0568(13) 0.0307(10) -0.0129(9) -0.0014(8) -0.0131(9) N10 0.0483(12) 0.0351(11) 0.0410(11) -0.0122(8) -0.0024(9) -0.0048(9) N11 0.0323(10) 0.0313(10) 0.0271(9) -0.0094(7) -0.0008(7) -0.0069(7) N12 0.0385(11) 0.0566(13) 0.0341(10) -0.0145(9) 0.0052(8) -0.0225(9) N13 0.0422(11) 0.0394(11) 0.0297(10) -0.0070(8) 0.0058(8) -0.0114(8) N14 0.0480(13) 0.0979(18) 0.0347(11) -0.0332(11) 0.0093(9) -0.0366(12) N15 0.0333(10) 0.0549(12) 0.0354(11) -0.0171(9) 0.0054(8) -0.0156(9) N16 0.0329(10) 0.0671(14) 0.0296(10) -0.0212(9) 0.0035(8) -0.0134(9) O1 0.0641(12) 0.0563(11) 0.0494(11) -0.0266(8) 0.0066(8) -0.0237(9) O2 0.0575(12) 0.1234(19) 0.0592(13) -0.0544(12) 0.0288(10) -0.0335(12) O3 0.0424(10) 0.0839(14) 0.0457(10) -0.0123(9) 0.0105(8) -0.0355(9) O4 0.0431(10) 0.0532(10) 0.0493(10) -0.0211(8) 0.0031(8) -0.0172(8) O5 0.0492(11) 0.0735(13) 0.0415(10) -0.0179(8) 0.0174(8) -0.0299(9) O6 0.0529(10) 0.0757(12) 0.0264(9) -0.0135(8) 0.0005(7) -0.0165(9) O7 0.0584(12) 0.1061(16) 0.0528(11) -0.0436(11) 0.0169(9) -0.0520(11) O8 0.0483(11) 0.0999(15) 0.0447(11) -0.0346(10) 0.0195(8) -0.0349(10) C1 0.0490(15) 0.0509(16) 0.0379(13) -0.0015(11) 0.0097(11) -0.0129(12) C2 0.0334(13) 0.0465(14) 0.0445(14) 0.0014(10) 0.0003(10) -0.0013(10) C3 0.0266(11) 0.0357(12) 0.0288(11) -0.0034(9) 0.0050(8) -0.0068(9) C4 0.0320(12) 0.0304(11) 0.0327(11) -0.0051(9) 0.0018(9) -0.0058(9) C5 0.0312(12) 0.0380(12) 0.0318(11) -0.0111(9) 0.0033(9) -0.0047(9) C6 0.0299(12) 0.0461(14) 0.0352(12) -0.0077(10) 0.0056(9) -0.0045(10) C7 0.0265(11) 0.0373(12) 0.0288(11) -0.0048(9) -0.0001(8) -0.0079(9) C8 0.0293(11) 0.0367(12) 0.0282(11) -0.0055(9) -0.0011(8) -0.0021(9) C9 0.0439(14) 0.0478(15) 0.0361(12) -0.0180(10) 0.0046(10) -0.0175(11) C10 0.0332(12) 0.0428(13) 0.0299(11) -0.0056(9) -0.0005(9) -0.0043(10) C11 0.0310(11) 0.0321(11) 0.0245(10) -0.0086(8) -0.0034(8) -0.0052(9) C12 0.0302(11) 0.0274(11) 0.0333(11) -0.0043(8) -0.0009(9) -0.0062(8) C13 0.0357(12) 0.0343(12) 0.0230(10) -0.0090(8) 0.0039(8) -0.0074(9) C14 0.0319(11) 0.0402(13) 0.0285(11) -0.0114(9) 0.0000(9) -0.0067(9) C15 0.0273(11) 0.0375(12) 0.0292(11) -0.0106(9) 0.0019(8) -0.0080(9) C16 0.0315(11) 0.0327(11) 0.0249(11) -0.0063(8) -0.0020(8) -0.0027(9) 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 C2 N1 C1 101.80(19) C1 N2 N3 101.54(19) C2 N3 N2 108.93(18) C2 N3 C3 129.31(19) N2 N3 C3 121.75(17) C4 N4 H4A 120.0 C4 N4 H4B 120.0 H4A N4 H4B 120.0 O1 N5 O2 117.77(18) O1 N5 C5 120.82(18) O2 N5 C5 121.40(19) C6 N6 H6A 120.0 C6 N6 H6B 120.0 H6A N6 H6B 120.0 O4 N7 O3 117.33(17) O4 N7 C7 121.66(17) O3 N7 C7 121.01(17) C8 N8 H8A 120.0 C8 N8 H8B 120.0 H8A N8 H8B 120.0 C10 N9 C9 102.19(18) C9 N10 N11 101.89(19) C10 N11 N10 109.01(17) C10 N11 C11 129.89(18) N10 N11 C11 121.09(17) C12 N12 H12A 120.0 C12 N12 H12B 120.0 H12A N12 H12B 120.0 O5 N13 O6 118.72(17) O5 N13 C13 121.19(17) O6 N13 C13 120.08(18) C14 N14 H14A 120.0 C14 N14 H14B 120.0 H14A N14 H14B 120.0 O8 N15 O7 117.57(18) O8 N15 C15 121.55(17) O7 N15 C15 120.85(17) C16 N16 H16A 120.0 C16 N16 H16B 120.0 H16A N16 H16B 120.0 N2 C1 N1 116.2(2) N2 C1 H1A 121.9 N1 C1 H1A 121.9 N1 C2 N3 111.5(2) N1 C2 H2A 124.2 N3 C2 H2A 124.2 C8 C3 C4 123.80(18) C8 C3 N3 118.31(17) C4 C3 N3 117.78(18) N4 C4 C3 118.53(19) N4 C4 C5 123.00(18) C3 C4 C5 118.47(18) N5 C5 C6 120.29(19) N5 C5 C4 119.42(18) C6 C5 C4 120.27(18) N6 C6 C5 120.9(2) N6 C6 C7 120.6(2) C5 C6 C7 118.52(18) N7 C7 C8 119.06(17) N7 C7 C6 120.33(18) C8 C7 C6 120.58(18) N8 C8 C3 119.20(19) N8 C8 C7 122.79(18) C3 C8 C7 118.01(17) N10 C9 N9 115.7(2) N10 C9 H9 122.1 N9 C9 H9 122.1 N9 C10 N11 111.2(2) N9 C10 H10 124.4 N11 C10 H10 124.4 C16 C11 C12 124.35(18) C16 C11 N11 117.92(17) C12 C11 N11 117.69(18) N12 C12 C11 119.15(18) N12 C12 C13 122.93(19) C11 C12 C13 117.90(18) N13 C13 C14 120.09(17) N13 C13 C12 119.20(18) C14 C13 C12 120.67(18) N14 C14 C13 121.04(19) N14 C14 C15 120.75(19) C13 C14 C15 118.21(17) N15 C15 C14 120.02(17) N15 C15 C16 119.18(17) C14 C15 C16 120.80(18) N16 C16 C11 119.80(18) N16 C16 C15 122.97(18) C11 C16 C15 117.23(17) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C2 1.308(3) N1 C1 1.340(3) N2 C1 1.313(3) N2 N3 1.361(3) N3 C2 1.329(3) N3 C3 1.431(2) N4 C4 1.323(3) N4 H4A 0.8600 N4 H4B 0.8600 N5 O1 1.236(2) N5 O2 1.242(2) N5 C5 1.404(3) N6 C6 1.318(3) N6 H6A 0.8600 N6 H6B 0.8600 N7 O4 1.240(2) N7 O3 1.253(2) N7 C7 1.394(3) N8 C8 1.325(3) N8 H8A 0.8600 N8 H8B 0.8600 N9 C10 1.307(3) N9 C9 1.352(3) N10 C9 1.303(3) N10 N11 1.368(2) N11 C10 1.329(3) N11 C11 1.430(2) N12 C12 1.325(3) N12 H12A 0.8600 N12 H12B 0.8600 N13 O5 1.234(2) N13 O6 1.246(2) N13 C13 1.408(3) N14 C14 1.314(3) N14 H14A 0.8600 N14 H14B 0.8600 N15 O8 1.238(2) N15 O7 1.245(2) N15 C15 1.392(3) N16 C16 1.325(3) N16 H16A 0.8600 N16 H16B 0.8600 C1 H1A 0.9300 C2 H2A 0.9300 C3 C8 1.390(3) C3 C4 1.393(3) C4 C5 1.436(3) C5 C6 1.431(3) C6 C7 1.440(3) C7 C8 1.438(3) C9 H9 0.9300 C10 H10 0.9300 C11 C16 1.388(3) C11 C12 1.394(3) C12 C13 1.433(3) C13 C14 1.432(3) C14 C15 1.433(3) C15 C16 1.443(3) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C10 H10 O8 0.93 2.57 3.187(3) 124.1 1_455 C9 H9 O1 0.93 2.50 3.293(3) 143.5 2 C2 H2A O4 0.93 2.60 3.308(3) 133.0 1_455 C2 H2A O3 0.93 2.56 3.350(3) 142.4 1_455 C2 H2A N7 0.93 2.59 3.270(3) 130.2 1_455 N16 H16B O8 0.86 1.91 2.539(2) 129.0 . N16 H16A N9 0.86 2.17 2.949(2) 150.5 2 N14 H14B O7 0.86 1.85 2.501(3) 131.2 . N14 H14A O6 0.86 1.86 2.510(3) 131.2 . N14 H14A N1 0.86 2.56 3.273(3) 141.0 2_566 N12 H12B O5 0.86 1.90 2.538(2) 130.0 . N12 H12A O3 0.86 2.21 3.016(2) 155.9 1_445 N8 H8B O4 0.86 1.89 2.527(2) 129.5 . N8 H8A O6 0.86 2.13 2.924(2) 153.0 2_566 N6 H6B O3 0.86 1.85 2.507(2) 132.3 . N6 H6A O2 0.86 2.50 3.172(3) 135.9 2_665 N6 H6A O2 0.86 1.86 2.518(3) 132.3 . N4 H4B O1 0.86 1.90 2.534(2) 129.1 . N4 H4A O7 0.86 2.12 2.909(3) 151.8 1_455 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 C1 N2 N3 C2 0.5(2) C1 N2 N3 C3 -178.47(18) C9 N10 N11 C10 0.0(2) C9 N10 N11 C11 179.02(18) N3 N2 C1 N1 -0.4(3) C2 N1 C1 N2 0.1(3) C1 N1 C2 N3 0.2(2) N2 N3 C2 N1 -0.4(3) C3 N3 C2 N1 178.40(19) C2 N3 C3 C8 80.7(3) N2 N3 C3 C8 -100.6(2) C2 N3 C3 C4 -95.5(3) N2 N3 C3 C4 83.1(3) C8 C3 C4 N4 -173.6(2) N3 C3 C4 N4 2.4(3) C8 C3 C4 C5 6.3(3) N3 C3 C4 C5 -177.70(19) O1 N5 C5 C6 178.7(2) O2 N5 C5 C6 -2.2(4) O1 N5 C5 C4 -2.6(3) O2 N5 C5 C4 176.4(2) N4 C4 C5 N5 -4.7(3) C3 C4 C5 N5 175.4(2) N4 C4 C5 C6 174.0(2) C3 C4 C5 C6 -6.0(3) N5 C5 C6 N6 0.3(4) C4 C5 C6 N6 -178.3(2) N5 C5 C6 C7 -179.9(2) C4 C5 C6 C7 1.5(3) O4 N7 C7 C8 -1.9(3) O3 N7 C7 C8 177.6(2) O4 N7 C7 C6 176.3(2) O3 N7 C7 C6 -4.3(3) N6 C6 C7 N7 4.6(4) C5 C6 C7 N7 -175.2(2) N6 C6 C7 C8 -177.3(2) C5 C6 C7 C8 3.0(3) C4 C3 C8 N8 177.6(2) N3 C3 C8 N8 1.6(3) C4 C3 C8 C7 -1.9(3) N3 C3 C8 C7 -177.89(18) N7 C7 C8 N8 -4.2(3) C6 C7 C8 N8 177.6(2) N7 C7 C8 C3 175.33(19) C6 C7 C8 C3 -2.9(3) N11 N10 C9 N9 0.1(2) C10 N9 C9 N10 -0.2(3) C9 N9 C10 N11 0.2(2) N10 N11 C10 N9 -0.2(2) C11 N11 C10 N9 -179.06(19) C10 N11 C11 C16 -92.1(3) N10 N11 C11 C16 89.1(2) C10 N11 C11 C12 90.2(3) N10 N11 C11 C12 -88.5(2) C16 C11 C12 N12 -179.9(2) N11 C11 C12 N12 -2.4(3) C16 C11 C12 C13 -1.2(3) N11 C11 C12 C13 176.33(18) O5 N13 C13 C14 168.6(2) O6 N13 C13 C14 -10.9(3) O5 N13 C13 C12 -9.1(3) O6 N13 C13 C12 171.5(2) N12 C12 C13 N13 3.2(3) C11 C12 C13 N13 -175.42(18) N12 C12 C13 C14 -174.4(2) C11 C12 C13 C14 6.9(3) N13 C13 C14 N14 -1.5(3) C12 C13 C14 N14 176.1(2) N13 C13 C14 C15 178.09(19) C12 C13 C14 C15 -4.3(3) O8 N15 C15 C14 173.7(2) O7 N15 C15 C14 -8.0(3) O8 N15 C15 C16 -5.4(3) O7 N15 C15 C16 172.9(2) N14 C14 C15 N15 -3.5(3) C13 C14 C15 N15 176.9(2) N14 C14 C15 C16 175.5(2) C13 C14 C15 C16 -4.0(3) C12 C11 C16 N16 173.9(2) N11 C11 C16 N16 -3.5(3) C12 C11 C16 C15 -6.9(3) N11 C11 C16 C15 175.63(18) N15 C15 C16 N16 7.7(3) C14 C15 C16 N16 -171.4(2) N15 C15 C16 C11 -171.5(2) C14 C15 C16 C11 9.4(3)