#------------------------------------------------------------------------------ #$Date: 2018-11-09 04:58:05 +0200 (Fri, 09 Nov 2018) $ #$Revision: 211867 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/02/1550205.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_1550205 loop_ _publ_author_name 'Dawn, Arnab' 'Mirzamani, Marzieh' 'Jones, Christopher David' 'Yufit, Dimitrii S.' 'Qian, Shuo' 'Steed, Jonathan W.' 'Kumari, Harshita' _publ_section_title ; Investigating the effect of supramolecular gel phase crystallization on gel nucleation ; _journal_name_full 'Soft Matter' _journal_paper_doi 10.1039/C8SM01916A _journal_year 2018 _chemical_formula_moiety 'C22 H38 N4 O2' _chemical_formula_sum 'C22 H38 N4 O2' _chemical_formula_weight 390.56 _chemical_name_systematic ; ? ; _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2014-09-18 _audit_creation_method ; Olex2 1.2-beta (compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874) ; _audit_update_record ; 2018-06-25 deposited with the CCDC. 2018-11-07 downloaded from the CCDC. ; _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 8.9115(2) _cell_length_b 16.2345(3) _cell_length_c 32.4328(7) _cell_measurement_reflns_used 9973 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 30.43 _cell_measurement_theta_min 2.51 _cell_volume 4692.17(17) _computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)' _computing_data_collection 'APEX2 v.2013.4_1 (Bruker, 2013)' _computing_data_reduction 'SAINT v8.34A (Bruker, 2013)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'XS (Sheldrick, 2008)' _diffrn_ambient_temperature 120.0 _diffrn_detector 'Bruker PHOTON 100 CMOS' _diffrn_detector_type 'CMOS sensor' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device 'Bruker D8 Venture' _diffrn_measurement_device_type D8Venture _diffrn_measurement_method \w-scan _diffrn_radiation_monochromator 'focusing mirrors' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1116 _diffrn_reflns_av_unetI/netI 0.0578 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_number 55636 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.51 _diffrn_source 'ImuS microsource' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.072 _exptl_absorpt_correction_T_max 0.9856 _exptl_absorpt_correction_T_min 0.6809 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1575 before and 0.1258 after correction. The Ratio of minimum to maximum transmission is 0.6908. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'dull light colourless' _exptl_crystal_colour_lustre dull _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.106 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plank _exptl_crystal_F_000 1712 _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.402 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.087 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 288 _refine_ls_number_reflns 5388 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.029 _refine_ls_R_factor_all 0.0934 _refine_ls_R_factor_gt 0.0637 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.8000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1549 _refine_ls_wR_factor_ref 0.1738 _reflns_number_gt 3810 _reflns_number_total 5388 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL 14srv204 in Pbca #61 CELL 0.71073 8.9115 16.2345 32.4328 90 90 90 ZERR 8 0.0002 0.0003 0.0007 0 0 0 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,-Z SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 176 304 32 16 EQIV $1 1.5-X,-0.5+Y,+Z EQIV $2 0.5-X,0.5+Y,+Z L.S. 9 PLAN 5 TEMP -153.15 HTAB N1 O2_$1 HTAB N2 O2_$1 HTAB N3 O1_$2 HTAB N4 O1_$2 CONF C9 C10 C11 C12 CONF C11 C10 C9 N2 CONF C10 C9 N2 C8 CONF C1 C7 N1 C8 CONF C13 C7 N1 C8 CONF C14 C7 N1 C8 CONF C2 C1 C7 N1 CONF C6 C1 C7 N1 CONF C2 C1 C7 C13 CONF C6 C1 C7 C13 CONF C2 C1 C7 C14 CONF C6 C1 C7 C14 CONF C2 C3 C15 N3 CONF C2 C3 C15 C21 CONF C2 C3 C15 C22 CONF C4 C3 C15 N3 CONF C4 C3 C15 C21 CONF C4 C3 C15 C22 CONF C3 C15 N3 C16 CONF C21 C15 N3 C16 CONF C22 C15 N3 C16 CONF C18 C17 N4 C16 CONF C18A C17 N4 C16 CONF C19 C18 C17 N4 CONF C19 C18 C17 C18A CONF C17 C18 C19 C20 REM reset to Pbca #61 BOND $h fmap 2 53 acta OMIT -2 55 OMIT 0 2 0 REM D:/Struc/14S/14srv204/14srv204.hkl WGHT 0.1 0.8 FVAR 0.06667 O1 4 0.51282 0.15249 0.12428 11.00000 0.01892 0.02672 0.04391 = 0.00111 0.00046 0.00046 O2 4 0.48493 0.63793 0.16042 11.00000 0.01909 0.02470 0.04448 = 0.00018 -0.00077 -0.00126 N1 3 0.72143 0.21210 0.15212 11.00000 0.01825 0.02577 0.03875 = -0.00395 -0.00047 0.00433 N2 3 0.73506 0.08501 0.12194 11.00000 0.02071 0.02982 0.05117 = -0.00941 -0.00229 0.00352 N3 3 0.24785 0.58535 0.16006 11.00000 0.01636 0.02100 0.04025 = 0.00327 -0.00236 0.00129 N4 3 0.29529 0.70998 0.13048 11.00000 0.02095 0.02508 0.04479 = 0.00794 0.00174 -0.00010 C1 1 0.55220 0.33414 0.15534 11.00000 0.02160 0.02014 0.02986 = 0.00009 -0.00020 -0.00218 C2 1 0.46517 0.39050 0.17717 11.00000 0.02321 0.02495 0.02193 = 0.00084 -0.00084 -0.00116 C3 1 0.38361 0.45224 0.15792 11.00000 0.02149 0.01929 0.02670 = -0.00076 -0.00081 -0.00259 C4 1 0.38977 0.45735 0.11514 11.00000 0.03008 0.02119 0.02929 = 0.00340 -0.00398 -0.00087 C5 1 0.47428 0.40138 0.09287 11.00000 0.03328 0.02618 0.02383 = -0.00044 0.00131 -0.00369 C6 1 0.55585 0.34004 0.11266 11.00000 0.02617 0.02175 0.02939 = -0.00169 0.00351 -0.00139 C7 1 0.64734 0.27213 0.17921 11.00000 0.02827 0.02710 0.02955 = -0.00258 -0.00135 0.00609 C8 1 0.64830 0.14992 0.13241 11.00000 0.02028 0.02364 0.03191 = 0.00381 0.00467 0.00042 C9 1 0.68171 0.01929 0.09527 11.00000 0.02749 0.02291 0.04120 = -0.00452 0.00300 -0.00096 C10 1 0.73144 0.02942 0.05069 11.00000 0.03103 0.02567 0.04531 = 0.00374 0.00596 0.00017 C11 1 0.68463 -0.04295 0.02394 11.00000 0.04028 0.03195 0.03685 = 0.00240 0.00413 -0.00003 C12 1 0.73805 -0.03479 -0.02060 11.00000 0.05743 0.04519 0.03949 = 0.00445 0.01264 0.00257 C13 1 0.55523 0.22672 0.21200 11.00000 0.05627 0.03494 0.03445 = 0.01061 0.00978 0.01942 C14 1 0.77462 0.31991 0.19983 11.00000 0.03905 0.04653 0.05045 = -0.01852 -0.01986 0.01765 C15 1 0.27955 0.50926 0.18252 11.00000 0.02439 0.01917 0.02901 = 0.00141 -0.00022 0.00038 C16 1 0.35079 0.64408 0.15091 11.00000 0.02043 0.02030 0.03373 = -0.00250 0.00307 0.00228 C17 1 0.38908 0.77867 0.11841 11.00000 0.03532 0.01986 0.03975 = 0.00179 0.00246 -0.00327 PART 1 C18 1 0.47263 0.76403 0.07791 10.80000 0.03219 0.02794 0.04730 = 0.00579 0.00784 -0.00430 C19 1 0.36795 0.76518 0.04106 10.80000 0.05947 0.03492 0.03727 = -0.00147 0.00320 -0.00653 C20 1 0.44563 0.74766 0.00058 10.80000 0.10364 0.04866 0.04871 = -0.00712 0.01913 -0.00705 PART 0 C21 1 0.34027 0.52954 0.22557 11.00000 0.03588 0.02622 0.02972 = -0.00549 -0.00037 0.00301 C22 1 0.12746 0.46586 0.18708 11.00000 0.02689 0.02386 0.03760 = 0.00041 0.00523 -0.00102 H1 2 0.81924 0.20236 0.15663 11.00000 0.02852 H3 2 0.15758 0.59461 0.15171 11.00000 0.02374 H4 2 0.20179 0.70994 0.12502 11.00000 0.02388 H2 2 0.82496 0.08667 0.12889 11.00000 0.03379 PART 2 C19A 1 0.49651 0.72350 0.05328 10.20000 0.05014 C18A 1 0.39236 0.78672 0.06989 10.20000 0.04468 C20A 1 0.50578 0.72246 0.00667 10.20000 0.05925 HKLF 4 END ; _cod_data_source_file c8sm01916a2.cif _cod_data_source_block G_14srv204 _cod_depositor_comments ; The following automatic conversions were performed: '_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according to /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas ; _cod_database_code 1550205 _computing.bruker_data_scaling 'SADABS V2012/1 (Bruker AXS Inc.)' _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Others Fixed Sof: H17A(0.8) H17B(0.8) H17C(0.2) H17D(0.2) C18(0.8) H18A(0.8) H18B(0.8) C19(0.8) H19A(0.8) H19B(0.8) C20(0.8) H20A(0.8) H20B(0.8) H20C(0.8) C19A(0.2) H19C(0.2) H19D(0.2) C18A(0.2) H18C(0.2) H18D(0.2) C20A(0.2) H20D(0.2) H20E(0.2) H20F(0.2) 3.a Secondary CH2 refined with riding coordinates: C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C17(H17A,H17B), C17(H17C,H17D), C18(H18A,H18B), C19(H19A,H19B), C19A(H19C,H19D), C18A(H18C,H18D) 3.b Aromatic/amide H refined with riding coordinates: C2(H2A), C4(H4A), C5(H5), C6(H6) 3.c Idealised Me refined as rotating group: C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C20(H20A,H20B, H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C20A(H20D,H20E,H20F) ; _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 '-x-1/2, y-1/2, z' 8 'x, -y-1/2, z-1/2' 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_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_refinement_flags_posn O1 O 0.51282(13) 0.15249(7) 0.12428(4) 0.0298(3) Uani 1 d . . . O2 O 0.48493(13) 0.63793(7) 0.16041(4) 0.0294(3) Uani 1 d . . . N1 N 0.72143(17) 0.21210(8) 0.15212(5) 0.0276(3) Uani 1 d . . . N2 N 0.73507(19) 0.08501(10) 0.12193(5) 0.0339(4) Uani 1 d . . . N3 N 0.24785(17) 0.58535(8) 0.16005(5) 0.0259(3) Uani 1 d . . . N4 N 0.29529(18) 0.70998(9) 0.13048(5) 0.0303(4) Uani 1 d B . . C1 C 0.55220(19) 0.33414(10) 0.15534(5) 0.0239(4) Uani 1 d . . . C2 C 0.46517(19) 0.39050(10) 0.17717(5) 0.0234(4) Uani 1 d . . . H2A H 0.4616 0.3865 0.2064 0.028 Uiso 1 calc . . R C3 C 0.38361(18) 0.45224(9) 0.15792(5) 0.0225(4) Uani 1 d . . . C4 C 0.3898(2) 0.45735(10) 0.11514(5) 0.0269(4) Uani 1 d . . . H4A H 0.3358 0.4994 0.1012 0.032 Uiso 1 calc . . R C5 C 0.4743(2) 0.40138(10) 0.09287(5) 0.0278(4) Uani 1 d . . . H5 H 0.4766 0.4049 0.0636 0.033 Uiso 1 calc . . R C6 C 0.5558(2) 0.34004(10) 0.11266(5) 0.0258(4) Uani 1 d . . . H6 H 0.6139 0.3022 0.0970 0.031 Uiso 1 calc . . R C7 C 0.6473(2) 0.27213(11) 0.17921(5) 0.0283(4) Uani 1 d . . . C8 C 0.64830(19) 0.14992(10) 0.13241(5) 0.0253(4) Uani 1 d . . . C9 C 0.6817(2) 0.01929(10) 0.09527(6) 0.0305(4) Uani 1 d . . . H9A H 0.5707 0.0178 0.0963 0.037 Uiso 1 calc . . R H9B H 0.7193 -0.0341 0.1058 0.037 Uiso 1 calc . . R C10 C 0.7314(2) 0.02942(11) 0.05069(6) 0.0340(4) Uani 1 d . . . H10A H 0.6873 0.0806 0.0394 0.041 Uiso 1 calc . . R H10B H 0.8420 0.0351 0.0498 0.041 Uiso 1 calc . . R C11 C 0.6846(2) -0.04295(11) 0.02394(6) 0.0364(5) Uani 1 d . . . H11A H 0.5738 -0.0475 0.0242 0.044 Uiso 1 calc . . R H11B H 0.7260 -0.0943 0.0359 0.044 Uiso 1 calc . . R C12 C 0.7380(3) -0.03479(13) -0.02060(6) 0.0474(6) Uani 1 d . . . H12A H 0.7002 -0.0813 -0.0368 0.071 Uiso 1 calc . . GR H12B H 0.8480 -0.0347 -0.0213 0.071 Uiso 1 calc . . GR H12C H 0.7002 0.0168 -0.0323 0.071 Uiso 1 calc . . GR C13 C 0.5552(3) 0.22672(12) 0.21200(6) 0.0419(5) Uani 1 d . . . H13A H 0.4714 0.1980 0.1988 0.063 Uiso 1 calc . . GR H13B H 0.5161 0.2665 0.2320 0.063 Uiso 1 calc . . GR H13C H 0.6193 0.1867 0.2262 0.063 Uiso 1 calc . . GR C14 C 0.7746(2) 0.31991(14) 0.19983(7) 0.0453(6) Uani 1 d . . . H14A H 0.8396 0.2815 0.2148 0.068 Uiso 1 calc . . GR H14B H 0.7324 0.3601 0.2192 0.068 Uiso 1 calc . . GR H14C H 0.8334 0.3487 0.1788 0.068 Uiso 1 calc . . GR C15 C 0.27955(19) 0.50926(10) 0.18252(5) 0.0242(4) Uani 1 d . . . C16 C 0.35079(19) 0.64408(10) 0.15091(5) 0.0248(4) Uani 1 d . . . C17 C 0.3891(2) 0.77867(10) 0.11841(6) 0.0316(4) Uani 1 d . . . H17A H 0.4632 0.7894 0.1405 0.038 Uiso 0.80 calc A 1 R H17B H 0.3257 0.8284 0.1156 0.038 Uiso 0.80 calc A 1 R H17C H 0.4923 0.7702 0.1289 0.038 Uiso 0.20 calc A 2 R H17D H 0.3495 0.8301 0.1306 0.038 Uiso 0.20 calc A 2 R C18 C 0.4726(3) 0.76403(15) 0.07791(8) 0.0358(6) Uani 0.80 d B 1 . H18A H 0.5500 0.8072 0.0744 0.043 Uiso 0.80 calc B 1 R H18B H 0.5242 0.7101 0.0791 0.043 Uiso 0.80 calc B 1 R C19 C 0.3679(3) 0.76518(16) 0.04105(8) 0.0439(6) Uani 0.80 d B 1 . H19A H 0.2881 0.7236 0.0453 0.053 Uiso 0.80 calc B 1 R H19B H 0.3193 0.8199 0.0394 0.053 Uiso 0.80 calc B 1 R C20 C 0.4456(5) 0.7477(2) 0.00058(12) 0.0670(11) Uani 0.80 d B 1 . H20A H 0.5253 0.7883 -0.0039 0.101 Uiso 0.80 calc B 1 GR H20B H 0.3726 0.7510 -0.0220 0.101 Uiso 0.80 calc B 1 GR H20C H 0.4893 0.6923 0.0013 0.101 Uiso 0.80 calc B 1 GR C21 C 0.3403(2) 0.52954(11) 0.22557(5) 0.0306(4) Uani 1 d . . . H21A H 0.4391 0.5555 0.2230 0.046 Uiso 1 calc . . GR H21B H 0.3493 0.4787 0.2417 0.046 Uiso 1 calc . . GR H21C H 0.2712 0.5674 0.2395 0.046 Uiso 1 calc . . GR C22 C 0.12746(19) 0.46586(10) 0.18708(6) 0.0294(4) Uani 1 d . . . H22A H 0.0589 0.5011 0.2028 0.044 Uiso 1 calc . . GR H22B H 0.1413 0.4135 0.2016 0.044 Uiso 1 calc . . GR H22C H 0.0851 0.4553 0.1597 0.044 Uiso 1 calc . . GR H1 H 0.819(2) 0.2024(11) 0.1566(6) 0.029(5) Uiso 1 d . . . H3 H 0.158(2) 0.5946(11) 0.1517(5) 0.024(5) Uiso 1 d . . . H4 H 0.202(2) 0.7099(11) 0.1250(5) 0.024(5) Uiso 1 d . . . H2 H 0.825(3) 0.0867(13) 0.1289(6) 0.034(6) Uiso 1 d . . . C19A C 0.4965(14) 0.7235(8) 0.0533(4) 0.050(3) Uiso 0.20 d B 2 . H19C H 0.4635 0.6686 0.0629 0.060 Uiso 0.20 calc B 2 R H19D H 0.5980 0.7336 0.0646 0.060 Uiso 0.20 calc B 2 R C18A C 0.3924(14) 0.7867(7) 0.0699(4) 0.045(3) Uiso 0.20 d B 2 . H18C H 0.2904 0.7782 0.0585 0.054 Uiso 0.20 calc B 2 R H18D H 0.4269 0.8424 0.0619 0.054 Uiso 0.20 calc B 2 R C20A C 0.5058(19) 0.7225(10) 0.0067(5) 0.059(5) Uiso 0.20 d B 2 . H20D H 0.4073 0.7084 -0.0048 0.089 Uiso 0.20 calc B 2 GR H20E H 0.5797 0.6813 -0.0021 0.089 Uiso 0.20 calc B 2 GR H20F H 0.5363 0.7770 -0.0033 0.089 Uiso 0.20 calc B 2 GR 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 O1 0.0189(6) 0.0267(7) 0.0439(8) 0.0011(5) 0.0005(5) 0.0005(5) O2 0.0191(6) 0.0247(6) 0.0445(8) 0.0002(5) -0.0008(5) -0.0013(5) N1 0.0182(8) 0.0258(7) 0.0388(9) -0.0039(6) -0.0005(6) 0.0043(6) N2 0.0207(8) 0.0298(8) 0.0512(10) -0.0094(7) -0.0023(7) 0.0035(7) N3 0.0164(8) 0.0210(7) 0.0402(9) 0.0033(6) -0.0024(6) 0.0013(6) N4 0.0210(8) 0.0251(8) 0.0448(9) 0.0079(6) 0.0017(7) -0.0001(6) C1 0.0216(8) 0.0201(8) 0.0299(9) 0.0001(6) -0.0002(7) -0.0022(6) C2 0.0232(9) 0.0249(8) 0.0219(8) 0.0008(6) -0.0008(6) -0.0012(7) C3 0.0215(8) 0.0193(8) 0.0267(9) -0.0008(6) -0.0008(6) -0.0026(6) C4 0.0301(9) 0.0212(8) 0.0293(9) 0.0034(6) -0.0040(7) -0.0009(7) C5 0.0333(10) 0.0262(9) 0.0238(8) -0.0004(7) 0.0013(7) -0.0037(7) C6 0.0262(9) 0.0217(8) 0.0294(9) -0.0017(6) 0.0035(7) -0.0014(7) C7 0.0283(9) 0.0271(9) 0.0296(9) -0.0026(7) -0.0013(7) 0.0061(7) C8 0.0203(9) 0.0236(8) 0.0319(9) 0.0038(7) 0.0047(7) 0.0004(7) C9 0.0275(10) 0.0229(8) 0.0412(10) -0.0045(7) 0.0030(8) -0.0010(7) C10 0.0310(10) 0.0257(9) 0.0453(11) 0.0037(8) 0.0060(8) 0.0002(8) C11 0.0403(11) 0.0319(10) 0.0369(10) 0.0024(8) 0.0041(9) 0.0000(8) C12 0.0574(14) 0.0452(12) 0.0395(12) 0.0044(9) 0.0126(10) 0.0026(10) C13 0.0563(13) 0.0349(10) 0.0345(11) 0.0106(8) 0.0098(9) 0.0194(10) C14 0.0391(12) 0.0465(12) 0.0505(13) -0.0185(10) -0.0199(10) 0.0177(10) C15 0.0244(9) 0.0192(8) 0.0290(9) 0.0014(6) -0.0002(7) 0.0004(7) C16 0.0204(9) 0.0203(8) 0.0337(9) -0.0025(7) 0.0031(7) 0.0023(7) C17 0.0353(10) 0.0199(8) 0.0397(10) 0.0018(7) 0.0025(8) -0.0033(8) C18 0.0322(14) 0.0279(12) 0.0473(15) 0.0058(11) 0.0078(11) -0.0043(11) C19 0.0595(18) 0.0349(13) 0.0373(14) -0.0015(11) 0.0032(12) -0.0065(12) C20 0.104(3) 0.049(2) 0.0487(19) -0.0071(15) 0.019(2) -0.007(2) C21 0.0359(10) 0.0262(9) 0.0297(9) -0.0055(7) -0.0004(8) 0.0030(8) C22 0.0269(9) 0.0239(9) 0.0376(10) 0.0004(7) 0.0052(8) -0.0010(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 C7 N1 H1 117.1(12) C8 N1 C7 123.91(14) C8 N1 H1 114.3(12) C8 N2 C9 122.36(16) C8 N2 H2 117.2(14) C9 N2 H2 120.0(14) C15 N3 H3 119.0(12) C16 N3 C15 124.92(15) C16 N3 H3 116.1(12) C16 N4 C17 122.07(16) C16 N4 H4 117.3(12) C17 N4 H4 120.6(12) C2 C1 C7 118.98(15) C6 C1 C2 118.34(15) C6 C1 C7 122.56(15) C1 C2 H2A 118.7 C3 C2 C1 122.53(15) C3 C2 H2A 118.7 C2 C3 C4 118.14(15) C2 C3 C15 121.25(14) C4 C3 C15 120.44(14) C3 C4 H4A 119.9 C5 C4 C3 120.19(15) C5 C4 H4A 119.9 C4 C5 H5 119.5 C4 C5 C6 120.94(16) C6 C5 H5 119.5 C1 C6 C5 119.85(16) C1 C6 H6 120.1 C5 C6 H6 120.1 N1 C7 C1 112.57(14) N1 C7 C13 109.67(15) N1 C7 C14 105.36(14) C1 C7 C13 111.82(15) C1 C7 C14 107.42(15) C14 C7 C13 109.74(17) O1 C8 N1 122.86(15) O1 C8 N2 122.13(16) N2 C8 N1 115.01(15) N2 C9 H9A 109.0 N2 C9 H9B 109.0 N2 C9 C10 113.01(15) H9A C9 H9B 107.8 C10 C9 H9A 109.0 C10 C9 H9B 109.0 C9 C10 H10A 109.1 C9 C10 H10B 109.1 H10A C10 H10B 107.9 C11 C10 C9 112.29(15) C11 C10 H10A 109.1 C11 C10 H10B 109.1 C10 C11 H11A 109.0 C10 C11 H11B 109.0 C10 C11 C12 112.81(16) H11A C11 H11B 107.8 C12 C11 H11A 109.0 C12 C11 H11B 109.0 C11 C12 H12A 109.5 C11 C12 H12B 109.5 C11 C12 H12C 109.5 H12A C12 H12B 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 C7 C13 H13A 109.5 C7 C13 H13B 109.5 C7 C13 H13C 109.5 H13A C13 H13B 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 C7 C14 H14A 109.5 C7 C14 H14B 109.5 C7 C14 H14C 109.5 H14A C14 H14B 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 N3 C15 C3 111.56(13) N3 C15 C21 109.92(14) N3 C15 C22 105.38(14) C3 C15 C22 107.87(13) C21 C15 C3 112.95(14) C21 C15 C22 108.83(14) O2 C16 N3 122.81(15) O2 C16 N4 122.60(15) N4 C16 N3 114.59(15) N4 C17 H17A 108.9 N4 C17 H17B 108.9 N4 C17 H17C 109.6 N4 C17 H17D 109.6 N4 C17 C18 113.19(16) N4 C17 C18A 110.1(5) H17A C17 H17B 107.8 H17A C17 H17C 32.5 H17A C17 H17D 78.4 H17B C17 H17C 132.5 H17B C17 H17D 31.3 H17C C17 H17D 108.2 C18 C17 H17A 108.9 C18 C17 H17B 108.9 C18 C17 H17C 79.7 C18 C17 H17D 130.5 C18 C17 C18A 31.5(4) C18A C17 H17A 134.0 C18A C17 H17B 81.4 C18A C17 H17C 109.6 C18A C17 H17D 109.6 C17 C18 H18A 109.2 C17 C18 H18B 109.2 H18A C18 H18B 107.9 C19 C18 C17 112.1(2) C19 C18 H18A 109.2 C19 C18 H18B 109.2 C18 C19 H19A 108.8 C18 C19 H19B 108.8 H19A C19 H19B 107.7 C20 C19 C18 113.6(3) C20 C19 H19A 108.8 C20 C19 H19B 108.8 C15 C21 H21A 109.5 C15 C21 H21B 109.5 C15 C21 H21C 109.5 H21A C21 H21B 109.5 H21A C21 H21C 109.5 H21B C21 H21C 109.5 C15 C22 H22A 109.5 C15 C22 H22B 109.5 C15 C22 H22C 109.5 H22A C22 H22B 109.5 H22A C22 H22C 109.5 H22B C22 H22C 109.5 H19C C19A H19D 107.7 C18A C19A H19C 108.8 C18A C19A H19D 108.8 C18A C19A C20A 113.8(11) C20A C19A H19C 108.8 C20A C19A H19D 108.8 C17 C18A H18C 110.0 C17 C18A H18D 110.0 C19A C18A C17 108.4(9) C19A C18A H18C 110.0 C19A C18A H18D 110.0 H18C C18A H18D 108.4 C19A C20A H20D 109.5 C19A C20A H20E 109.5 C19A C20A H20F 109.5 H20D C20A H20E 109.5 H20D C20A H20F 109.5 H20E C20A H20F 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C8 1.236(2) O2 C16 1.239(2) N1 C7 1.469(2) N1 C8 1.361(2) N1 H1 0.90(2) N2 C8 1.350(2) N2 C9 1.453(2) N2 H2 0.83(2) N3 C15 1.462(2) N3 C16 1.356(2) N3 H3 0.86(2) N4 C16 1.352(2) N4 C17 1.448(2) N4 H4 0.85(2) C1 C2 1.393(2) C1 C6 1.388(2) C1 C7 1.527(2) C2 H2A 0.9500 C2 C3 1.387(2) C3 C4 1.391(2) C3 C15 1.534(2) C4 H4A 0.9500 C4 C5 1.384(2) C5 H5 0.9500 C5 C6 1.390(2) C6 H6 0.9500 C7 C13 1.532(3) C7 C14 1.528(3) C9 H9A 0.9900 C9 H9B 0.9900 C9 C10 1.521(3) C10 H10A 0.9900 C10 H10B 0.9900 C10 C11 1.519(3) C11 H11A 0.9900 C11 H11B 0.9900 C11 C12 1.527(3) C12 H12A 0.9800 C12 H12B 0.9800 C12 H12C 0.9800 C13 H13A 0.9800 C13 H13B 0.9800 C13 H13C 0.9800 C14 H14A 0.9800 C14 H14B 0.9800 C14 H14C 0.9800 C15 C21 1.533(2) C15 C22 1.535(2) C17 H17A 0.9900 C17 H17B 0.9900 C17 H17C 0.9900 C17 H17D 0.9900 C17 C18 1.529(3) C17 C18A 1.579(12) C18 H18A 0.9900 C18 H18B 0.9900 C18 C19 1.516(4) C19 H19A 0.9900 C19 H19B 0.9900 C19 C20 1.511(4) C20 H20A 0.9800 C20 H20B 0.9800 C20 H20C 0.9800 C21 H21A 0.9800 C21 H21B 0.9800 C21 H21C 0.9800 C22 H22A 0.9800 C22 H22B 0.9800 C22 H22C 0.9800 C19A H19C 0.9900 C19A H19D 0.9900 C19A C18A 1.485(16) C19A C20A 1.51(2) C18A H18C 0.9900 C18A H18D 0.9900 C20A H20D 0.9800 C20A H20E 0.9800 C20A H20F 0.9800 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 N1 H1 O2 0.90(2) 2.04(2) 2.8930(19) 158.6(17) 7_755 N3 H3 O1 0.86(2) 1.99(2) 2.8160(19) 158.8(17) 7_665 N4 H4 O1 0.85(2) 2.13(2) 2.907(2) 151.9(17) 7_665 N2 H2 O2 0.83(2) 2.15(2) 2.919(2) 154.3(19) 7_755 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 C7 N1 C8 -72.6(2) C2 C1 C7 N1 174.63(15) C2 C1 C7 C13 50.6(2) C2 C1 C7 C14 -69.8(2) C2 C3 C15 N3 159.76(15) C2 C3 C15 C21 35.3(2) C2 C3 C15 C22 -84.96(18) C3 C15 N3 C16 -66.1(2) C4 C3 C15 N3 -25.1(2) C4 C3 C15 C21 -149.49(15) C4 C3 C15 C22 90.20(18) C6 C1 C7 N1 -9.4(2) C6 C1 C7 C13 -133.43(17) C6 C1 C7 C14 106.11(18) C9 C10 C11 C12 -178.24(17) C10 C9 N2 C8 98.3(2) C11 C10 C9 N2 175.73(16) C13 C7 N1 C8 52.6(2) C14 C7 N1 C8 170.62(17) C17 C18 C19 C20 -177.8(2) C18 C17 N4 C16 83.4(2) C19 C18 C17 N4 70.8(2) C19 C18 C17 C18A -20.2(8) C21 C15 N3 C16 60.0(2) C22 C15 N3 C16 177.09(15) C18A C17 N4 C16 117.2(5)