#------------------------------------------------------------------------------ #$Date: 2021-10-16 03:26:48 +0300 (Sat, 16 Oct 2021) $ #$Revision: 269975 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/10/7061024.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_7061024 loop_ _publ_author_name 'Garcia-Raso, Angel' 'TERRON, ANGEL' 'FIOL, JUAN J J' 'Lopez-Zafra, Adela' 'Massanet, Barbara' 'Frontera, Antonio' 'Barcel\'o-Oliver, Miquel' _publ_section_title ; Modified-amino acid/peptide pyrimidine analogs: Synthesis, structural characterization and DFT study of N-(pyrimidyl) gabapentine and N-(pyrimidyl)baclofen ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D1NJ04639J _journal_year 2021 _chemical_formula_moiety 'C13 H19 N3 O2' _chemical_formula_sum 'C13 H19 N3 O2' _chemical_formula_weight 249.31 _space_group_crystal_system monoclinic _space_group_IT_number 7 _space_group_name_Hall 'P -2yc' _space_group_name_H-M_alt 'P 1 c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2020-11-23 _audit_creation_method ; Olex2 1.3 (compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145) ; _audit_update_record ; 2021-09-01 deposited with the CCDC. 2021-10-15 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 92.168(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 16.6291(18) _cell_length_b 7.1628(8) _cell_length_c 10.9025(11) _cell_measurement_reflns_used 8997 _cell_measurement_temperature 293.15 _cell_measurement_theta_max 68.223 _cell_measurement_theta_min 6.731 _cell_volume 1297.7(2) _computing_cell_refinement 'Bruker Apex3, 2016' _computing_data_collection 'Bruker Apex3, 2016' _computing_data_reduction 'SAINT v8.40A (Bruker, 2019)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'XT (Sheldrick, 2015)' _diffrn_ambient_temperature 293.15 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Bruker D8 Venture' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator multilayer _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0576 _diffrn_reflns_av_unetI/netI 0.0495 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 28675 _diffrn_reflns_point_group_measured_fraction_full 0.958 _diffrn_reflns_point_group_measured_fraction_max 0.954 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 68.340 _diffrn_reflns_theta_min 6.178 _diffrn_source 'high brilliance microfocus sealed tube' _diffrn_source_current 1.2 _diffrn_source_power 0.06 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.711 _exptl_absorpt_correction_T_max 0.7531 _exptl_absorpt_correction_T_min 0.3312 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1658 before and 0.1036 after correction. The Ratio of minimum to maximum transmission is 0.4398. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.276 _exptl_crystal_description plate _exptl_crystal_F_000 536 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.491 _refine_diff_density_min -0.478 _refine_diff_density_rms 0.112 _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack 0.1(3) _refine_ls_extinction_coef 0.028(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 329 _refine_ls_number_reflns 4547 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.109 _refine_ls_R_factor_all 0.0635 _refine_ls_R_factor_gt 0.0629 _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^)+(0.1173P)^2^+0.0433P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1496 _refine_ls_wR_factor_ref 0.1505 _reflns_Friedel_coverage 0.918 _reflns_Friedel_fraction_full 0.920 _reflns_Friedel_fraction_max 0.915 _reflns_number_gt 4445 _reflns_number_total 4547 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj04639j2.cif _cod_data_source_block 1_a_CCDC1 _cod_database_code 7061024 _shelx_shelxl_version_number 2018/3 _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_max 0.926 _shelx_estimated_absorpt_t_min 0.740 _olex2_refinement_description ; 1. Twinned data refinement Scales: 0.9(3) 0.1(3) 2. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All O(H) groups 3.a Secondary CH2 refined with riding coordinates: C8(H8A,H8B), C10(H10A,H10B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C8'(H8'A,H8'B), C10'(H10C,H10D), C14'(H14C, H14D), C15'(H15C,H15D), C16'(H16C,H16D), C17'(H17C,H17D), C18'(H18C,H18D) 3.b Aromatic/amide H refined with riding coordinates: N7(H7), C4(H4), C5(H5), C6(H6), N7'(H7'), C4'(H4'), C5'(H5'), C6'(H6') 3.c Idealised tetrahedral OH refined as rotating group: O13(H13), O13'(H13') ; _shelx_res_file ; TITL 1_a.res in Pc 1_a.res created by SHELXL-2018/3 at 11:13:00 on 23-Nov-2020 REM Old TITL 1 in P2(1)/c REM SHELXT solution in Pc: R1 0.139, Rweak 0.018, Alpha 0.000 REM 1.001 for 206 systematic absences, Orientation as input REM Flack x = 0.201 ( 0.098 ) from 2081 Parsons' quotients REM Formula found by SHELXT: C25 N6 O5 CELL 1.54178 16.6291 7.1628 10.9025 90 92.168 90 ZERR 4 0.0018 0.0008 0.0011 0 0.004 0 LATT -1 SYMM +X,-Y,0.5+Z SFAC C H N O UNIT 52 76 12 8 EQIV $1 +X,1-Y,-0.5+Z EQIV $2 +X,1-Y,0.5+Z EQIV $3 +X,1+Y,+Z EQIV $4 +X,2-Y,0.5+Z EQIV $5 +X,2-Y,-0.5+Z EQIV $6 +X,-Y,-0.5+Z EQIV $7 +X,-Y,0.5+Z L.S. 10 PLAN 2 SIZE 0.11 0.21 0.45 TEMP 21 CONF HTAB O13 N1_$1 HTAB O13 N7_$1 HTAB N7 O12_$2 HTAB N7 O13_$2 HTAB C4 O13'_$3 HTAB C5 O13'_$2 HTAB C6 N3_$4 HTAB C6 N3'_$2 HTAB C8 N1_$5 HTAB C10 O12_$2 HTAB C14 O12_$2 HTAB C17 O12 HTAB C18 O12_$3 HTAB O13' N1'_$6 HTAB O13' N7'_$6 HTAB N7' O12'_$7 HTAB N7' O13'_$7 HTAB C4' O13 HTAB C5' O13_$2 HTAB C6' N3_$2 HTAB C6' N3'_$2 HTAB C8' N1'_$1 HTAB C10' O12'_$7 HTAB C14' O12'_$3 HTAB C15' O12' HTAB C18' O12'_$7 BOND LIST 4 MORE -1 BOND $H fmap 2 acta TWIN -1 0 0 0 -1 0 0 0 -1 2 REM REM REM WGHT 0.117300 0.043300 EXTI 0.028349 BASF 0.05831 FVAR 1.17653 O12 4 0.203822 0.325062 0.270092 11.00000 0.05585 0.06219 = 0.06678 -0.02652 -0.00393 0.00550 O13 4 0.310926 0.372307 0.393240 11.00000 0.05770 0.06875 = 0.05430 -0.01695 -0.00649 0.02183 AFIX 147 H13 2 0.333141 0.311358 0.340606 11.00000 -1.50000 AFIX 0 N1 3 0.398458 0.822623 0.738600 11.00000 0.05189 0.04068 = 0.04089 -0.00381 0.00016 -0.00937 N3 3 0.445347 0.873583 0.537653 11.00000 0.04499 0.05474 = 0.04276 -0.00095 0.00622 -0.01023 N7 3 0.313379 0.798309 0.569261 11.00000 0.04214 0.05875 = 0.03458 -0.00316 0.00558 -0.00856 AFIX 43 H7 2 0.276140 0.767244 0.617947 11.00000 -1.20000 AFIX 0 C2 1 0.387434 0.833168 0.616477 11.00000 0.04703 0.03202 = 0.03976 -0.00250 0.00572 -0.00473 C4 1 0.519033 0.897912 0.588118 11.00000 0.04542 0.04978 = 0.05538 -0.00603 0.00699 -0.00978 AFIX 43 H4 2 0.560813 0.924244 0.536473 11.00000 -1.20000 AFIX 0 C5 1 0.536506 0.886291 0.711403 11.00000 0.04808 0.04957 = 0.05971 0.00142 -0.00630 -0.01059 AFIX 43 H5 2 0.588529 0.902213 0.744065 11.00000 -1.20000 AFIX 0 C6 1 0.472275 0.849455 0.784792 11.00000 0.06320 0.04955 = 0.04310 0.00092 -0.00766 -0.01554 AFIX 43 H6 2 0.481300 0.843358 0.869402 11.00000 -1.20000 AFIX 0 C8 1 0.293831 0.811389 0.437579 11.00000 0.04520 0.04769 = 0.03955 0.00074 0.00481 -0.01011 AFIX 23 H8A 2 0.331500 0.735082 0.393860 11.00000 -1.20000 H8B 2 0.300821 0.939704 0.411609 11.00000 -1.20000 AFIX 0 C9 1 0.207990 0.748970 0.401627 11.00000 0.04154 0.03243 = 0.03737 0.00118 0.00169 -0.00110 C10 1 0.193064 0.541586 0.436873 11.00000 0.04568 0.03451 = 0.03760 0.00213 0.00795 -0.00145 AFIX 23 H10A 2 0.210945 0.522860 0.521700 11.00000 -1.20000 H10B 2 0.135669 0.517198 0.431030 11.00000 -1.20000 AFIX 0 C11 1 0.235191 0.402687 0.357897 11.00000 0.04901 0.03328 = 0.04140 0.00168 0.00344 -0.00072 C14 1 0.147295 0.872915 0.466398 11.00000 0.05287 0.03828 = 0.06067 -0.00869 0.00597 0.00486 AFIX 23 H14A 2 0.163282 1.002422 0.458227 11.00000 -1.20000 H14B 2 0.149078 0.842751 0.553193 11.00000 -1.20000 AFIX 0 C15 1 0.060279 0.850584 0.415334 11.00000 0.05004 0.05782 = 0.08403 -0.01469 0.00222 0.01240 AFIX 23 H15A 2 0.041079 0.726346 0.434153 11.00000 -1.20000 H15B 2 0.025973 0.940116 0.454848 11.00000 -1.20000 AFIX 0 C16 1 0.054681 0.880880 0.276285 11.00000 0.06105 0.06059 = 0.08996 0.00141 -0.01853 0.01312 AFIX 23 H16A 2 0.000009 0.857321 0.246068 11.00000 -1.20000 H16B 2 0.067727 1.009652 0.257986 11.00000 -1.20000 AFIX 0 C17 1 0.111799 0.752485 0.211743 11.00000 0.06181 0.05026 = 0.05353 0.00688 -0.01595 -0.00314 AFIX 23 H17A 2 0.108922 0.777859 0.124293 11.00000 -1.20000 H17B 2 0.095930 0.623726 0.224051 11.00000 -1.20000 AFIX 0 C18 1 0.198170 0.780969 0.261516 11.00000 0.05431 0.04030 = 0.04109 0.00618 -0.00223 -0.00351 AFIX 23 H18A 2 0.215030 0.907121 0.242837 11.00000 -1.20000 H18B 2 0.233331 0.695613 0.219967 11.00000 -1.20000 AFIX 0 O12' 4 0.796714 -0.172453 0.303596 11.00000 0.05729 0.06312 = 0.06340 -0.02471 0.01061 -0.00520 O13' 4 0.689270 -0.128686 0.415620 11.00000 0.05540 0.07124 = 0.05906 -0.01968 0.01779 -0.02135 AFIX 147 H13' 2 0.669066 -0.202493 0.365902 11.00000 -1.50000 AFIX 0 N1' 3 0.602363 0.322153 0.750850 11.00000 0.05030 0.04168 = 0.04102 -0.00302 0.00834 0.00886 N3' 3 0.555298 0.373572 0.544348 11.00000 0.04257 0.05424 = 0.04150 -0.00218 0.00242 0.01019 N7' 3 0.687308 0.297157 0.590751 11.00000 0.04226 0.05765 = 0.03551 -0.00043 0.00372 0.01034 AFIX 43 H7' 2 0.724528 0.265526 0.643616 11.00000 -1.20000 AFIX 0 C2' 1 0.612472 0.333021 0.629457 11.00000 0.04395 0.03270 = 0.04057 -0.00381 0.00404 0.00452 C4' 1 0.481062 0.398862 0.586512 11.00000 0.04436 0.05130 = 0.05438 -0.00599 0.00243 0.01040 AFIX 43 H4' 2 0.439242 0.425939 0.530274 11.00000 -1.20000 AFIX 0 C5' 1 0.464184 0.386737 0.707539 11.00000 0.04729 0.04987 = 0.06261 0.00031 0.01342 0.01015 AFIX 43 H5' 2 0.412150 0.403143 0.734039 11.00000 -1.20000 AFIX 0 C6' 1 0.527200 0.349292 0.788714 11.00000 0.05900 0.05203 = 0.04405 0.00258 0.01714 0.01337 AFIX 43 H6' 2 0.517691 0.342499 0.872108 11.00000 -1.20000 AFIX 0 C8' 1 0.706289 0.310817 0.461973 11.00000 0.04208 0.04822 = 0.03703 -0.00046 0.00065 0.01039 AFIX 23 H8'A 2 0.698658 0.438963 0.435219 11.00000 -1.20000 H8'B 2 0.668909 0.233540 0.414076 11.00000 -1.20000 AFIX 0 C9' 1 0.792577 0.250386 0.435801 11.00000 0.04095 0.03334 = 0.03293 0.00234 0.00348 0.00455 C10' 1 0.807540 0.041833 0.472288 11.00000 0.04539 0.03425 = 0.03743 0.00308 -0.00242 0.00210 AFIX 23 H10C 2 0.864958 0.017672 0.473421 11.00000 -1.20000 H10D 2 0.789421 0.022456 0.554855 11.00000 -1.20000 AFIX 0 C11' 1 0.765963 -0.096301 0.388174 11.00000 0.04557 0.03476 = 0.04028 0.00152 0.00586 0.00001 C14' 1 0.803476 0.283776 0.297970 11.00000 0.04826 0.04105 = 0.03725 0.00489 0.00740 0.00599 AFIX 23 H14C 2 0.768858 0.198615 0.251235 11.00000 -1.20000 H14D 2 0.786673 0.410033 0.277527 11.00000 -1.20000 AFIX 0 C15' 1 0.890111 0.256254 0.260457 11.00000 0.05504 0.05543 = 0.04747 0.00282 0.01839 0.00240 AFIX 23 H15C 2 0.905837 0.127337 0.274312 11.00000 -1.20000 H15D 2 0.893865 0.282522 0.173580 11.00000 -1.20000 AFIX 0 C16' 1 0.946623 0.383268 0.333050 11.00000 0.05909 0.06214 = 0.07796 0.00212 0.01742 -0.01272 AFIX 23 H16C 2 0.934278 0.512164 0.312576 11.00000 -1.20000 H16D 2 1.001504 0.358584 0.310604 11.00000 -1.20000 AFIX 0 C17' 1 0.939724 0.354792 0.471123 11.00000 0.04642 0.05434 = 0.06829 -0.00455 0.00146 -0.00878 AFIX 23 H17C 2 0.972865 0.446443 0.514732 11.00000 -1.20000 H17D 2 0.959813 0.231778 0.493413 11.00000 -1.20000 AFIX 0 C18' 1 0.852706 0.373481 0.510199 11.00000 0.04648 0.04010 = 0.04882 -0.00472 0.00195 -0.00196 AFIX 23 H18C 2 0.836326 0.502937 0.501590 11.00000 -1.20000 H18D 2 0.850339 0.340721 0.596315 11.00000 -1.20000 AFIX 0 HKLF 4 REM 1_a.res in Pc REM wR2 = 0.150486, GooF = S = 1.10887, Restrained GooF = 1.10861 for all data REM R1 = 0.062949 for 4445 Fo > 4sig(Fo) and 0.063492 for all 4547 data REM 329 parameters refined using 2 restraints END WGHT 0.1173 0.0433 REM Highest difference peak 0.491, deepest hole -0.478, 1-sigma level 0.112 Q1 1 0.7998 0.2584 0.3670 11.00000 0.05 0.49 Q2 1 0.6979 0.2961 0.5220 11.00000 0.05 0.45 ; _shelx_res_checksum 29802 _olex2_exptl_crystal_mounting_method 'cryoloop, covered with Parabar 10320 (formerly known as Paratone)' _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' 'x, -y, 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O12 O 0.20382(17) 0.3251(4) 0.2701(3) 0.0618(7) Uani 1 1 d . . . . . O13 O 0.31093(17) 0.3723(4) 0.3932(2) 0.0605(7) Uani 1 1 d . . . . . H13 H 0.333141 0.311358 0.340606 0.091 Uiso 1 1 calc R U . . . N1 N 0.39846(17) 0.8226(4) 0.7386(2) 0.0445(6) Uani 1 1 d . . . . . N3 N 0.44535(17) 0.8736(4) 0.5377(2) 0.0474(6) Uani 1 1 d . . . . . N7 N 0.31338(16) 0.7983(4) 0.5693(2) 0.0450(6) Uani 1 1 d . . . . . H7 H 0.276140 0.767244 0.617947 0.054 Uiso 1 1 calc R U . . . C2 C 0.38743(18) 0.8332(4) 0.6165(3) 0.0395(6) Uani 1 1 d . . . . . C4 C 0.5190(2) 0.8979(5) 0.5881(3) 0.0501(7) Uani 1 1 d . . . . . H4 H 0.560813 0.924244 0.536473 0.060 Uiso 1 1 calc R U . . . C5 C 0.5365(2) 0.8863(5) 0.7114(4) 0.0527(8) Uani 1 1 d . . . . . H5 H 0.588529 0.902213 0.744065 0.063 Uiso 1 1 calc R U . . . C6 C 0.4723(2) 0.8495(4) 0.7848(3) 0.0522(8) Uani 1 1 d . . . . . H6 H 0.481300 0.843358 0.869402 0.063 Uiso 1 1 calc R U . . . C8 C 0.29383(19) 0.8114(4) 0.4376(3) 0.0441(7) Uani 1 1 d . . . . . H8A H 0.331500 0.735082 0.393860 0.053 Uiso 1 1 calc R U . . . H8B H 0.300821 0.939704 0.411609 0.053 Uiso 1 1 calc R U . . . C9 C 0.20799(16) 0.7490(4) 0.4016(3) 0.0371(6) Uani 1 1 d . . . . . C10 C 0.19306(17) 0.5416(4) 0.4369(2) 0.0391(6) Uani 1 1 d . . . . . H10A H 0.210945 0.522860 0.521700 0.047 Uiso 1 1 calc R U . . . H10B H 0.135669 0.517198 0.431030 0.047 Uiso 1 1 calc R U . . . C11 C 0.23519(19) 0.4027(4) 0.3579(3) 0.0412(6) Uani 1 1 d . . . . . C14 C 0.1473(2) 0.8729(4) 0.4664(3) 0.0505(8) Uani 1 1 d . . . . . H14A H 0.163282 1.002422 0.458227 0.061 Uiso 1 1 calc R U . . . H14B H 0.149078 0.842751 0.553193 0.061 Uiso 1 1 calc R U . . . C15 C 0.0603(2) 0.8506(6) 0.4153(5) 0.0640(10) Uani 1 1 d . . . . . H15A H 0.041079 0.726346 0.434153 0.077 Uiso 1 1 calc R U . . . H15B H 0.025973 0.940116 0.454848 0.077 Uiso 1 1 calc R U . . . C16 C 0.0547(3) 0.8809(6) 0.2763(5) 0.0711(11) Uani 1 1 d . . . . . H16A H 0.000009 0.857321 0.246068 0.085 Uiso 1 1 calc R U . . . H16B H 0.067727 1.009652 0.257986 0.085 Uiso 1 1 calc R U . . . C17 C 0.1118(2) 0.7525(5) 0.2117(3) 0.0557(8) Uani 1 1 d . . . . . H17A H 0.108922 0.777859 0.124293 0.067 Uiso 1 1 calc R U . . . H17B H 0.095930 0.623726 0.224051 0.067 Uiso 1 1 calc R U . . . C18 C 0.19817(19) 0.7810(5) 0.2615(3) 0.0453(7) Uani 1 1 d . . . . . H18A H 0.215030 0.907121 0.242837 0.054 Uiso 1 1 calc R U . . . H18B H 0.233331 0.695613 0.219967 0.054 Uiso 1 1 calc R U . . . O12' O 0.79671(16) -0.1725(4) 0.3036(3) 0.0611(7) Uani 1 1 d . . . . . O13' O 0.68927(17) -0.1287(4) 0.4156(3) 0.0615(7) Uani 1 1 d . . . . . H13' H 0.669066 -0.202493 0.365902 0.092 Uiso 1 1 calc R U . . . N1' N 0.60236(17) 0.3222(4) 0.7509(2) 0.0442(6) Uani 1 1 d . . . . . N3' N 0.55530(17) 0.3736(4) 0.5443(2) 0.0461(6) Uani 1 1 d . . . . . N7' N 0.68731(15) 0.2972(4) 0.5908(2) 0.0451(6) Uani 1 1 d . . . . . H7' H 0.724528 0.265526 0.643616 0.054 Uiso 1 1 calc R U . . . C2' C 0.61247(18) 0.3330(4) 0.6295(3) 0.0390(6) Uani 1 1 d . . . . . C4' C 0.4811(2) 0.3989(5) 0.5865(3) 0.0500(7) Uani 1 1 d . . . . . H4' H 0.439242 0.425939 0.530274 0.060 Uiso 1 1 calc R U . . . C5' C 0.4642(2) 0.3867(5) 0.7075(4) 0.0530(8) Uani 1 1 d . . . . . H5' H 0.412150 0.403143 0.734039 0.064 Uiso 1 1 calc R U . . . C6' C 0.5272(2) 0.3493(5) 0.7887(3) 0.0513(8) Uani 1 1 d . . . . . H6' H 0.517691 0.342499 0.872108 0.062 Uiso 1 1 calc R U . . . C8' C 0.70629(18) 0.3108(4) 0.4620(3) 0.0425(6) Uani 1 1 d . . . . . H8'A H 0.698658 0.438963 0.435219 0.051 Uiso 1 1 calc R U . . . H8'B H 0.668909 0.233540 0.414076 0.051 Uiso 1 1 calc R U . . . C9' C 0.79258(17) 0.2504(4) 0.4358(3) 0.0357(6) Uani 1 1 d . . . . . C10' C 0.80754(17) 0.0418(4) 0.4723(3) 0.0391(6) Uani 1 1 d . . . . . H10C H 0.864958 0.017672 0.473421 0.047 Uiso 1 1 calc R U . . . H10D H 0.789421 0.022456 0.554855 0.047 Uiso 1 1 calc R U . . . C11' C 0.76596(18) -0.0963(4) 0.3882(3) 0.0401(6) Uani 1 1 d . . . . . C14' C 0.80348(18) 0.2838(4) 0.2980(3) 0.0420(6) Uani 1 1 d . . . . . H14C H 0.768858 0.198615 0.251235 0.050 Uiso 1 1 calc R U . . . H14D H 0.786673 0.410033 0.277527 0.050 Uiso 1 1 calc R U . . . C15' C 0.8901(2) 0.2563(5) 0.2605(3) 0.0522(8) Uani 1 1 d . . . . . H15C H 0.905837 0.127337 0.274312 0.063 Uiso 1 1 calc R U . . . H15D H 0.893865 0.282522 0.173580 0.063 Uiso 1 1 calc R U . . . C16' C 0.9466(3) 0.3833(6) 0.3330(4) 0.0660(10) Uani 1 1 d . . . . . H16C H 0.934278 0.512164 0.312576 0.079 Uiso 1 1 calc R U . . . H16D H 1.001504 0.358584 0.310604 0.079 Uiso 1 1 calc R U . . . C17' C 0.9397(2) 0.3548(5) 0.4711(4) 0.0564(8) Uani 1 1 d . . . . . H17C H 0.972865 0.446443 0.514732 0.068 Uiso 1 1 calc R U . . . H17D H 0.959813 0.231778 0.493413 0.068 Uiso 1 1 calc R U . . . C18' C 0.85271(19) 0.3735(4) 0.5102(3) 0.0451(7) Uani 1 1 d . . . . . H18C H 0.836326 0.502937 0.501590 0.054 Uiso 1 1 calc R U . . . H18D H 0.850339 0.340721 0.596315 0.054 Uiso 1 1 calc R U . . . 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 O12 0.0559(13) 0.0622(15) 0.0668(16) -0.0265(13) -0.0039(12) 0.0055(11) O13 0.0577(14) 0.0688(16) 0.0543(13) -0.0170(12) -0.0065(11) 0.0218(12) N1 0.0519(14) 0.0407(13) 0.0409(13) -0.0038(10) 0.0002(11) -0.0094(10) N3 0.0450(14) 0.0547(15) 0.0428(13) -0.0010(11) 0.0062(10) -0.0102(11) N7 0.0421(12) 0.0587(15) 0.0346(12) -0.0032(11) 0.0056(9) -0.0086(11) C2 0.0470(15) 0.0320(13) 0.0398(14) -0.0025(10) 0.0057(12) -0.0047(10) C4 0.0454(16) 0.0498(17) 0.0554(18) -0.0060(15) 0.0070(13) -0.0098(13) C5 0.0481(17) 0.0496(18) 0.0597(19) 0.0014(15) -0.0063(13) -0.0106(14) C6 0.0632(19) 0.0495(18) 0.0431(16) 0.0009(13) -0.0077(14) -0.0155(14) C8 0.0452(15) 0.0477(16) 0.0395(14) 0.0007(13) 0.0048(12) -0.0101(12) C9 0.0415(14) 0.0324(13) 0.0374(14) 0.0012(11) 0.0017(10) -0.0011(11) C10 0.0457(14) 0.0345(14) 0.0376(12) 0.0021(11) 0.0079(10) -0.0015(11) C11 0.0490(15) 0.0333(13) 0.0414(14) 0.0017(12) 0.0034(11) -0.0007(12) C14 0.0529(18) 0.0383(15) 0.061(2) -0.0087(14) 0.0060(15) 0.0049(13) C15 0.0500(19) 0.058(2) 0.084(3) -0.0147(18) 0.0022(17) 0.0124(15) C16 0.061(2) 0.061(2) 0.090(3) 0.001(2) -0.019(2) 0.0131(18) C17 0.0618(19) 0.0503(19) 0.0535(18) 0.0069(14) -0.0159(15) -0.0031(14) C18 0.0543(17) 0.0403(15) 0.0411(15) 0.0062(12) -0.0022(12) -0.0035(13) O12' 0.0573(13) 0.0631(15) 0.0634(16) -0.0247(12) 0.0106(12) -0.0052(11) O13' 0.0554(13) 0.0712(16) 0.0591(15) -0.0197(12) 0.0178(11) -0.0214(12) N1' 0.0503(14) 0.0417(14) 0.0410(13) -0.0030(11) 0.0083(10) 0.0089(11) N3' 0.0426(13) 0.0542(14) 0.0415(13) -0.0022(11) 0.0024(10) 0.0102(11) N7' 0.0423(13) 0.0576(15) 0.0355(12) -0.0004(11) 0.0037(10) 0.0103(11) C2' 0.0439(14) 0.0327(13) 0.0406(15) -0.0038(10) 0.0040(11) 0.0045(10) C4' 0.0444(15) 0.0513(17) 0.0544(17) -0.0060(15) 0.0024(13) 0.0104(13) C5' 0.0473(16) 0.0499(17) 0.063(2) 0.0003(15) 0.0134(14) 0.0101(13) C6' 0.0590(18) 0.0520(19) 0.0441(16) 0.0026(13) 0.0171(14) 0.0134(14) C8' 0.0421(14) 0.0482(15) 0.0370(14) -0.0005(12) 0.0006(11) 0.0104(12) C9' 0.0409(13) 0.0333(13) 0.0329(13) 0.0023(10) 0.0035(10) 0.0045(11) C10' 0.0454(14) 0.0342(13) 0.0374(12) 0.0031(11) -0.0024(10) 0.0021(11) C11' 0.0456(14) 0.0348(13) 0.0403(14) 0.0015(12) 0.0059(11) 0.0000(11) C14' 0.0483(15) 0.0410(14) 0.0373(14) 0.0049(12) 0.0074(11) 0.0060(12) C15' 0.0550(17) 0.055(2) 0.0475(17) 0.0028(15) 0.0184(13) 0.0024(14) C16' 0.059(2) 0.062(2) 0.078(3) 0.0021(19) 0.0174(18) -0.0127(17) C17' 0.0464(17) 0.0543(19) 0.068(2) -0.0045(15) 0.0015(15) -0.0088(14) C18' 0.0465(16) 0.0401(15) 0.0488(17) -0.0047(12) 0.0020(12) -0.0020(12) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 O13 H13 109.5 . . ? C6 N1 C2 117.4(3) . . ? C4 N3 C2 115.6(3) . . ? C2 N7 H7 118.9 . . ? C2 N7 C8 122.1(2) . . ? C8 N7 H7 118.9 . . ? N1 C2 N3 124.9(3) . . ? N1 C2 N7 117.4(3) . . ? N7 C2 N3 117.6(3) . . ? N3 C4 H4 118.2 . . ? N3 C4 C5 123.7(3) . . ? C5 C4 H4 118.2 . . ? C4 C5 H5 121.9 . . ? C4 C5 C6 116.1(3) . . ? C6 C5 H5 121.9 . . ? N1 C6 C5 122.2(3) . . ? N1 C6 H6 118.9 . . ? C5 C6 H6 118.9 . . ? N7 C8 H8A 108.8 . . ? N7 C8 H8B 108.8 . . ? N7 C8 C9 113.7(2) . . ? H8A C8 H8B 107.7 . . ? C9 C8 H8A 108.8 . . ? C9 C8 H8B 108.8 . . ? C8 C9 C10 111.8(2) . . ? C8 C9 C14 109.6(3) . . ? C8 C9 C18 105.8(2) . . ? C14 C9 C10 108.9(2) . . ? C14 C9 C18 108.8(3) . . ? C18 C9 C10 111.9(2) . . ? C9 C10 H10A 108.7 . . ? C9 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C11 C10 C9 114.0(2) . . ? C11 C10 H10A 108.7 . . ? C11 C10 H10B 108.7 . . ? O12 C11 O13 122.2(3) . . ? O12 C11 C10 124.1(3) . . ? O13 C11 C10 113.6(3) . . ? C9 C14 H14A 108.9 . . ? C9 C14 H14B 108.9 . . ? C9 C14 C15 113.5(3) . . ? H14A C14 H14B 107.7 . . ? C15 C14 H14A 108.9 . . ? C15 C14 H14B 108.9 . . ? C14 C15 H15A 109.4 . . ? C14 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? C16 C15 C14 111.4(4) . . ? C16 C15 H15A 109.4 . . ? C16 C15 H15B 109.4 . . ? C15 C16 H16A 109.4 . . ? C15 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? C17 C16 C15 111.0(3) . . ? C17 C16 H16A 109.4 . . ? C17 C16 H16B 109.4 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? C16 C17 C18 110.6(3) . . ? H17A C17 H17B 108.1 . . ? C18 C17 H17A 109.5 . . ? C18 C17 H17B 109.5 . . ? C9 C18 H18A 108.9 . . ? C9 C18 H18B 108.9 . . ? C17 C18 C9 113.1(3) . . ? C17 C18 H18A 108.9 . . ? C17 C18 H18B 108.9 . . ? H18A C18 H18B 107.8 . . ? C11' O13' H13' 109.5 . . ? C2' N1' C6' 116.5(3) . . ? C2' N3' C4' 115.5(3) . . ? C2' N7' H7' 119.2 . . ? C2' N7' C8' 121.6(3) . . ? C8' N7' H7' 119.2 . . ? N1' C2' N7' 116.6(3) . . ? N3' C2' N1' 125.8(3) . . ? N3' C2' N7' 117.6(3) . . ? N3' C4' H4' 118.4 . . ? N3' C4' C5' 123.2(3) . . ? C5' C4' H4' 118.4 . . ? C4' C5' H5' 121.4 . . ? C4' C5' C6' 117.2(3) . . ? C6' C5' H5' 121.4 . . ? N1' C6' C5' 121.7(3) . . ? N1' C6' H6' 119.1 . . ? C5' C6' H6' 119.1 . . ? N7' C8' H8'A 108.9 . . ? N7' C8' H8'B 108.9 . . ? N7' C8' C9' 113.5(2) . . ? H8'A C8' H8'B 107.7 . . ? C9' C8' H8'A 108.9 . . ? C9' C8' H8'B 108.9 . . ? C8' C9' C10' 111.3(2) . . ? C8' C9' C14' 106.4(2) . . ? C8' C9' C18' 109.5(2) . . ? C14' C9' C10' 111.9(2) . . ? C14' C9' C18' 109.1(2) . . ? C18' C9' C10' 108.6(2) . . ? C9' C10' H10C 108.7 . . ? C9' C10' H10D 108.7 . . ? H10C C10' H10D 107.6 . . ? C11' C10' C9' 114.2(2) . . ? C11' C10' H10C 108.7 . . ? C11' C10' H10D 108.7 . . ? O12' C11' O13' 121.9(3) . . ? O12' C11' C10' 124.7(3) . . ? O13' C11' C10' 113.4(2) . . ? C9' C14' H14C 109.0 . . ? C9' C14' H14D 109.0 . . ? H14C C14' H14D 107.8 . . ? C15' C14' C9' 112.9(3) . . ? C15' C14' H14C 109.0 . . ? C15' C14' H14D 109.0 . . ? C14' C15' H15C 109.5 . . ? C14' C15' H15D 109.5 . . ? H15C C15' H15D 108.0 . . ? C16' C15' C14' 110.9(3) . . ? C16' C15' H15C 109.5 . . ? C16' C15' H15D 109.5 . . ? C15' C16' H16C 109.3 . . ? C15' C16' H16D 109.3 . . ? C15' C16' C17' 111.6(3) . . ? H16C C16' H16D 108.0 . . ? C17' C16' H16C 109.3 . . ? C17' C16' H16D 109.3 . . ? C16' C17' H17C 109.3 . . ? C16' C17' H17D 109.3 . . ? C16' C17' C18' 111.7(3) . . ? H17C C17' H17D 107.9 . . ? C18' C17' H17C 109.3 . . ? C18' C17' H17D 109.3 . . ? C9' C18' H18C 108.8 . . ? C9' C18' H18D 108.8 . . ? C17' C18' C9' 113.9(3) . . ? C17' C18' H18C 108.8 . . ? C17' C18' H18D 108.8 . . ? H18C C18' H18D 107.7 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O12 C11 1.208(4) . ? O13 H13 0.8200 . ? O13 C11 1.321(4) . ? N1 C2 1.339(4) . ? N1 C6 1.323(5) . ? N3 C2 1.346(4) . ? N3 C4 1.335(4) . ? N7 H7 0.8600 . ? N7 C2 1.340(4) . ? N7 C8 1.463(4) . ? C4 H4 0.9300 . ? C4 C5 1.367(5) . ? C5 H5 0.9300 . ? C5 C6 1.384(5) . ? C6 H6 0.9300 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 C9 1.533(4) . ? C9 C10 1.557(4) . ? C9 C14 1.536(4) . ? C9 C18 1.547(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 C11 1.506(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C14 C15 1.539(5) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C15 C16 1.531(7) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C16 C17 1.514(6) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C17 C18 1.530(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? O12' C11' 1.202(4) . ? O13' H13' 0.8200 . ? O13' C11' 1.341(4) . ? N1' C2' 1.343(4) . ? N1' C6' 1.345(4) . ? N3' C2' 1.335(4) . ? N3' C4' 1.346(4) . ? N7' H7' 0.8600 . ? N7' C2' 1.354(4) . ? N7' C8' 1.454(4) . ? C4' H4' 0.9300 . ? C4' C5' 1.362(5) . ? C5' H5' 0.9300 . ? C5' C6' 1.372(6) . ? C6' H6' 0.9300 . ? C8' H8'A 0.9700 . ? C8' H8'B 0.9700 . ? C8' C9' 1.536(4) . ? C9' C10' 1.563(4) . ? C9' C14' 1.539(4) . ? C9' C18' 1.541(4) . ? C10' H10C 0.9700 . ? C10' H10D 0.9700 . ? C10' C11' 1.500(4) . ? C14' H14C 0.9700 . ? C14' H14D 0.9700 . ? C14' C15' 1.525(4) . ? C15' H15C 0.9700 . ? C15' H15D 0.9700 . ? C15' C16' 1.510(6) . ? C16' H16C 0.9700 . ? C16' H16D 0.9700 . ? C16' C17' 1.528(6) . ? C17' H17C 0.9700 . ? C17' H17D 0.9700 . ? C17' C18' 1.530(5) . ? C18' H18C 0.9700 . ? C18' H18D 0.9700 . ? 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 _geom_hbond_publ_flag O13 H13 N1 0.82 1.85 2.664(4) 170.5 2_564 yes O13 H13 N7 0.82 3.07 3.739(4) 141.0 2_564 yes N7 H7 O12 0.86 2.19 3.032(4) 167.3 2_565 yes N7 H7 O13 0.86 3.20 3.739(4) 123.5 2_565 yes C4 H4 O13' 0.93 2.58 3.463(4) 158.6 1_565 yes C5 H5 O13' 0.93 2.95 3.741(5) 143.9 2_565 yes C6 H6 N3 0.93 2.81 3.439(4) 125.6 2_575 yes C6 H6 N3' 0.93 2.72 3.489(4) 140.8 2_565 yes C8 H8B N1 0.97 3.05 3.859(4) 141.3 2_574 yes C10 H10A O12 0.97 2.93 3.754(4) 144.0 2_565 yes C14 H14B O12 0.97 2.78 3.691(5) 157.6 2_565 yes C17 H17B O12 0.97 2.82 3.471(5) 124.8 . yes C18 H18A O12 0.97 3.01 3.899(4) 152.2 1_565 yes O13' H13' N1' 0.82 1.85 2.653(4) 164.9 2_554 yes O13' H13' N7' 0.82 3.10 3.741(4) 136.7 2_554 yes N7' H7' O12' 0.86 2.18 3.029(4) 167.3 2 yes N7' H7' O13' 0.86 3.20 3.741(4) 123.3 2 yes C4' H4' O13 0.93 2.59 3.468(4) 158.4 . yes C5' H5' O13 0.93 2.94 3.737(5) 144.3 2_565 yes C6' H6' N3 0.93 2.70 3.471(4) 141.4 2_565 yes C6' H6' N3' 0.93 2.82 3.439(4) 124.8 2_565 yes C8' H8'A N1' 0.97 3.05 3.859(4) 142.1 2_564 yes C10' H10D O12' 0.97 2.92 3.742(4) 143.8 2 yes C14' H14D O12' 0.97 3.01 3.897(4) 153.0 1_565 yes C15' H15C O12' 0.97 2.84 3.481(5) 124.6 . yes C18' H18D O12' 0.97 2.74 3.660(4) 158.6 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N3 C4 C5 C6 -0.9(6) . . . . ? N7 C8 C9 C10 -60.3(3) . . . . ? N7 C8 C9 C14 60.6(3) . . . . ? N7 C8 C9 C18 177.7(3) . . . . ? C2 N1 C6 C5 -0.3(5) . . . . ? C2 N3 C4 C5 -0.9(5) . . . . ? C2 N7 C8 C9 174.8(3) . . . . ? C4 N3 C2 N1 2.3(5) . . . . ? C4 N3 C2 N7 -176.7(3) . . . . ? C4 C5 C6 N1 1.5(5) . . . . ? C6 N1 C2 N3 -1.8(5) . . . . ? C6 N1 C2 N7 177.3(3) . . . . ? C8 N7 C2 N1 178.1(3) . . . . ? C8 N7 C2 N3 -2.8(5) . . . . ? C8 C9 C10 C11 -72.1(3) . . . . ? C8 C9 C14 C15 167.4(3) . . . . ? C8 C9 C18 C17 -171.7(3) . . . . ? C9 C10 C11 O12 -96.3(4) . . . . ? C9 C10 C11 O13 83.6(3) . . . . ? C9 C14 C15 C16 -54.0(4) . . . . ? C10 C9 C14 C15 -70.1(4) . . . . ? C10 C9 C18 C17 66.3(3) . . . . ? C14 C9 C10 C11 166.7(3) . . . . ? C14 C9 C18 C17 -54.1(3) . . . . ? C14 C15 C16 C17 55.1(4) . . . . ? C15 C16 C17 C18 -56.7(4) . . . . ? C16 C17 C18 C9 57.5(4) . . . . ? C18 C9 C10 C11 46.4(3) . . . . ? C18 C9 C14 C15 52.2(4) . . . . ? N3' C4' C5' C6' 0.9(6) . . . . ? N7' C8' C9' C10' 60.8(3) . . . . ? N7' C8' C9' C14' -177.0(3) . . . . ? N7' C8' C9' C18' -59.2(3) . . . . ? C2' N1' C6' C5' -0.2(5) . . . . ? C2' N3' C4' C5' 0.7(5) . . . . ? C2' N7' C8' C9' -175.6(3) . . . . ? C4' N3' C2' N1' -2.4(5) . . . . ? C4' N3' C2' N7' 176.8(3) . . . . ? C4' C5' C6' N1' -1.2(5) . . . . ? C6' N1' C2' N3' 2.1(5) . . . . ? C6' N1' C2' N7' -177.0(3) . . . . ? C8' N7' C2' N1' -177.9(3) . . . . ? C8' N7' C2' N3' 2.9(5) . . . . ? C8' C9' C10' C11' 72.1(3) . . . . ? C8' C9' C14' C15' 171.9(3) . . . . ? C8' C9' C18' C17' -167.5(3) . . . . ? C9' C10' C11' O12' 95.6(4) . . . . ? C9' C10' C11' O13' -84.2(3) . . . . ? C9' C14' C15' C16' -57.5(4) . . . . ? C10' C9' C14' C15' -66.3(3) . . . . ? C10' C9' C18' C17' 70.8(3) . . . . ? C14' C9' C10' C11' -46.9(3) . . . . ? C14' C9' C18' C17' -51.4(3) . . . . ? C14' C15' C16' C17' 56.1(4) . . . . ? C15' C16' C17' C18' -53.5(4) . . . . ? C16' C17' C18' C9' 52.2(4) . . . . ? C18' C9' C10' C11' -167.4(2) . . . . ? C18' C9' C14' C15' 53.9(3) . . . . ? loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 0.9(3) 2 0.1(3)