#------------------------------------------------------------------------------ #$Date: 2024-01-06 09:56:22 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288784 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247604.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_7247604 loop_ _publ_author_name 'Manoharan, Deepak' 'Ahmad, Shamim' 'Tothadi, Srinu' 'Emmerling, Franziska' 'Bhattacharya, Biswajit' 'Ghosh, Soumyajit' _publ_section_title ; Linker size dependent mechanical properties of di-imine based molecular crystals ; _journal_issue 46 _journal_name_full CrystEngComm _journal_page_first 6416 _journal_page_last 6423 _journal_paper_doi 10.1039/D3CE00928A _journal_volume 25 _journal_year 2023 _chemical_formula_moiety 'C33 H50 N2 O2' _chemical_formula_sum 'C33 H50 N2 O2' _chemical_formula_weight 506.75 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_date 2023-02-14 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2023-08-01 deposited with the CCDC. 2023-10-31 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.550(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.9128(12) _cell_length_b 10.0522(9) _cell_length_c 29.338(3) _cell_measurement_reflns_used 9979 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 24.869 _cell_measurement_theta_min 2.316 _cell_volume 3218.2(6) _computing_cell_refinement 'SAINT V8.40B (?, 2016)' _computing_data_reduction 'SAINT V8.40B (?, 2016)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 298 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker D8 QUEST' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1273 _diffrn_reflns_av_unetI/netI 0.0401 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_number 122904 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.471 _diffrn_reflns_theta_min 2.142 _exptl_absorpt_coefficient_mu 0.064 _exptl_absorpt_correction_T_max 0.7410 _exptl_absorpt_correction_T_min 0.6926 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1153 before and 0.0837 after correction. The Ratio of minimum to maximum transmission is 0.9347. The \l/2 correction factor is Not present.' _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.046 _exptl_crystal_description block _exptl_crystal_F_000 1112 _exptl_crystal_size_max 0.424 _exptl_crystal_size_mid 0.232 _exptl_crystal_size_min 0.122 _refine_diff_density_max 0.713 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.059 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 348 _refine_ls_number_reflns 6640 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.031 _refine_ls_R_factor_all 0.1355 _refine_ls_R_factor_gt 0.0868 _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^)+(0.1396P)^2^+2.4416P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2487 _refine_ls_wR_factor_ref 0.3022 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3980 _reflns_number_total 6640 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ce00928a3.cif _cod_data_source_block mm_8_2_0ma_a _cod_depositor_comments 'Adding full bibliography for 7247601--7247604.cif.' _cod_database_code 7247604 _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 0.992 _shelx_estimated_absorpt_t_min 0.973 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Secondary CH2 refined with riding coordinates: C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B) 2.b Aromatic/amide H refined with riding coordinates: C2(H2A), C4(H4), C6(H6), C11(H11), C20(H20), C29(H29) 2.c Idealised Me refined as rotating group: C1(H1A,H1B,H1C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C21(H21A,H21B, H21C), C22(H22A,H22B,H22C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A, H28B,H28C), C30(H30A,H30B,H30C), C31A(H31A,H31B,H31C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C) 2.d Idealised tetrahedral OH refined as rotating group: O1(H1), O2(H2) ; _shelx_res_file ; TITL MM_8_2_0ma_a.res in P2(1)/c mm_8_2_0ma_a.res created by SHELXL-2018/3 at 10:11:49 on 14-Feb-2023 CELL 0.71073 10.9128 10.0522 29.3383 90 90.55 90 ZERR 4 0.0012 0.0009 0.003 0 0.004 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 132 200 8 8 L.S. 40 PLAN 10 0 0 SIZE 0.122 0.232 0.424 TEMP 24.85 HTAB CONF fmap 2 acta REM REM REM WGHT 0.139600 2.441600 FVAR 0.30656 O1 4 0.244502 0.548478 0.524073 11.00000 0.12176 0.04867 = 0.07804 0.00856 0.02250 0.01718 AFIX 147 H1 2 0.289844 0.531658 0.502705 11.00000 -1.50000 AFIX 0 O2 4 0.243976 0.028472 0.366023 11.00000 0.06563 0.08793 = 0.09813 -0.01905 0.02645 0.00666 AFIX 147 H2 2 0.272685 0.091700 0.380191 11.00000 -1.50000 AFIX 0 N1 3 0.407178 0.188438 0.399160 11.00000 0.09344 0.06284 = 0.06606 -0.01521 0.00768 0.00982 C2 1 0.550983 -0.066884 0.330663 11.00000 0.04679 0.05516 = 0.05643 -0.00331 -0.00400 0.00410 AFIX 43 H2A 2 0.631592 -0.040599 0.335931 11.00000 -1.20000 AFIX 0 C1 1 0.329152 1.167750 0.544500 11.00000 0.17088 0.08194 = 0.17841 0.01498 -0.06163 -0.03008 AFIX 137 H1A 2 0.364102 1.130606 0.571823 11.00000 -1.50000 H1B 2 0.324833 1.262766 0.547363 11.00000 -1.50000 H1C 2 0.379448 1.145080 0.518981 11.00000 -1.50000 AFIX 0 C34 1 0.198920 1.111103 0.536988 11.00000 0.09808 0.04824 = 0.07087 -0.00061 -0.00850 0.00118 C3 1 0.208939 0.960009 0.533341 11.00000 0.07066 0.04997 = 0.05700 0.00198 0.00076 0.00331 C4 1 0.270764 0.902281 0.498246 11.00000 0.07870 0.05370 = 0.05936 0.00759 0.00787 0.00495 AFIX 43 H4 2 0.305884 0.956393 0.476225 11.00000 -1.20000 AFIX 0 C5 1 0.282665 0.766175 0.494488 11.00000 0.07585 0.05635 = 0.05709 0.00558 0.00697 0.01207 C6 1 0.353935 0.714559 0.457029 11.00000 0.09871 0.06372 = 0.06413 0.00347 0.01640 0.00996 AFIX 43 H6 2 0.381741 0.774264 0.435233 11.00000 -1.20000 AFIX 0 N7 3 0.380580 0.592512 0.452266 11.00000 0.11407 0.06316 = 0.06961 -0.00565 0.02205 0.01002 C8 1 0.458987 0.556069 0.413779 11.00000 0.12360 0.07944 = 0.08532 -0.01545 0.03479 -0.00184 AFIX 23 H8A 2 0.454513 0.625241 0.390770 11.00000 -1.20000 H8B 2 0.543361 0.549866 0.424266 11.00000 -1.20000 AFIX 0 C9 1 0.421898 0.428732 0.393426 11.00000 0.13565 0.07220 = 0.06825 -0.01290 0.02560 0.00162 AFIX 23 H9A 2 0.464030 0.417970 0.364698 11.00000 -1.20000 H9B 2 0.334684 0.431829 0.386813 11.00000 -1.20000 AFIX 0 C10 1 0.447892 0.309245 0.422732 11.00000 0.11503 0.06391 = 0.06965 -0.01914 0.00742 0.00185 AFIX 23 H10A 2 0.535076 0.303701 0.429205 11.00000 -1.20000 H10B 2 0.405294 0.317729 0.451453 11.00000 -1.20000 AFIX 0 C11 1 0.488247 0.115254 0.380784 11.00000 0.07424 0.05647 = 0.05837 -0.00471 -0.00434 0.00573 AFIX 43 H11 2 0.570447 0.135743 0.385636 11.00000 -1.20000 AFIX 0 C12 1 0.457326 0.000757 0.352475 11.00000 0.06149 0.05137 = 0.05087 -0.00205 0.00166 0.00476 C13 1 0.335086 -0.037834 0.345163 11.00000 0.05649 0.05659 = 0.05893 0.00468 0.01344 0.00523 C14 1 0.307539 -0.144870 0.315844 11.00000 0.05016 0.05649 = 0.06721 0.00219 0.00746 -0.00522 C15 1 0.174507 -0.189809 0.306958 11.00000 0.04983 0.07905 = 0.10764 -0.00135 0.00800 -0.01284 C16 1 0.120499 -0.238012 0.351871 11.00000 0.09126 0.13779 = 0.15820 0.02217 0.04237 -0.04349 AFIX 137 H16A 2 0.167846 -0.311558 0.363246 11.00000 -1.50000 H16B 2 0.037302 -0.265877 0.346887 11.00000 -1.50000 H16C 2 0.122407 -0.166895 0.373706 11.00000 -1.50000 AFIX 0 C17 1 0.611692 -0.396352 0.281824 11.00000 0.09738 0.06759 = 0.12473 -0.00184 0.01905 0.02294 AFIX 137 H17A 2 0.619431 -0.418584 0.313544 11.00000 -1.50000 H17B 2 0.673559 -0.442280 0.264911 11.00000 -1.50000 H17C 2 0.532116 -0.422415 0.270820 11.00000 -1.50000 AFIX 0 C18 1 0.627579 -0.246225 0.275764 11.00000 0.05244 0.06428 = 0.06290 -0.00935 0.00488 0.00501 C19 1 0.528413 -0.171719 0.301457 11.00000 0.04941 0.05235 = 0.05094 -0.00026 0.00121 0.00215 C20 1 0.405667 -0.206524 0.295354 11.00000 0.05560 0.05306 = 0.05904 -0.00258 0.00102 -0.00285 AFIX 43 H20 2 0.388491 -0.277175 0.275849 11.00000 -1.20000 AFIX 0 C21 1 0.099040 -0.074000 0.286863 11.00000 0.05546 0.11648 = 0.17482 0.01465 -0.01969 -0.01038 AFIX 137 H21A 2 0.100181 -0.000531 0.307769 11.00000 -1.50000 H21B 2 0.016024 -0.102483 0.281872 11.00000 -1.50000 H21C 2 0.133873 -0.046792 0.258423 11.00000 -1.50000 AFIX 0 C22 1 0.168353 -0.305245 0.273030 11.00000 0.06748 0.13215 = 0.18955 -0.06081 -0.00865 -0.03028 AFIX 137 H22A 2 0.204798 -0.278582 0.244814 11.00000 -1.50000 H22B 2 0.084310 -0.329371 0.267708 11.00000 -1.50000 H22C 2 0.212090 -0.380217 0.285278 11.00000 -1.50000 AFIX 0 C23 1 0.229114 0.682264 0.527305 11.00000 0.07637 0.04707 = 0.05991 0.00616 0.00374 0.01166 C24 1 0.162693 0.736014 0.563326 11.00000 0.06809 0.05315 = 0.05572 0.01049 0.00518 0.00974 C25 1 0.098761 0.648631 0.598667 11.00000 0.08659 0.07110 = 0.07655 0.02823 0.02157 0.02092 C26 1 0.194787 0.567433 0.625254 11.00000 0.12596 0.11170 = 0.08363 0.04877 0.02321 0.04254 AFIX 137 H26A 2 0.235573 0.507781 0.604837 11.00000 -1.50000 H26B 2 0.155095 0.517168 0.648696 11.00000 -1.50000 H26C 2 0.253736 0.626577 0.638856 11.00000 -1.50000 AFIX 0 C27 1 0.008804 0.553170 0.574547 11.00000 0.10209 0.08786 = 0.14126 0.04201 0.02163 -0.00912 AFIX 137 H27A 2 -0.052379 0.603759 0.558441 11.00000 -1.50000 H27B 2 -0.029986 0.497642 0.596782 11.00000 -1.50000 H27C 2 0.052703 0.498605 0.553383 11.00000 -1.50000 AFIX 0 C28 1 0.028157 0.731712 0.633303 11.00000 0.14011 0.10802 = 0.10532 0.04042 0.06517 0.04224 AFIX 137 H28A 2 0.083944 0.789449 0.649276 11.00000 -1.50000 H28B 2 -0.011125 0.673731 0.654670 11.00000 -1.50000 H28C 2 -0.032668 0.784108 0.617704 11.00000 -1.50000 AFIX 0 C29 1 0.156391 0.873840 0.564968 11.00000 0.07036 0.05799 = 0.05049 0.00098 0.00302 0.01002 AFIX 43 H29 2 0.113842 0.911774 0.589012 11.00000 -1.20000 AFIX 0 C30 1 0.156841 1.169181 0.492751 11.00000 0.19982 0.06499 = 0.12998 0.00936 -0.03442 0.03244 AFIX 137 H30A 2 0.166420 1.264083 0.493619 11.00000 -1.50000 H30B 2 0.072094 1.147580 0.487720 11.00000 -1.50000 H30C 2 0.204924 1.133259 0.468440 11.00000 -1.50000 AFIX 0 PART 1 C31A 1 0.126573 1.152571 0.576502 11.00000 0.40103 0.05756 = 0.19933 -0.01223 0.16346 0.02232 AFIX 137 H31A 2 0.147487 1.097931 0.602261 11.00000 -1.50000 H31B 2 0.040892 1.142940 0.569547 11.00000 -1.50000 H31C 2 0.144067 1.243940 0.583517 11.00000 -1.50000 AFIX 0 PART 0 C32 1 0.616086 -0.215921 0.225212 11.00000 0.11097 0.12415 = 0.07391 -0.00688 0.02028 0.02647 AFIX 137 H32A 2 0.673032 -0.269825 0.208653 11.00000 -1.50000 H32B 2 0.633790 -0.123627 0.220045 11.00000 -1.50000 H32C 2 0.534170 -0.235146 0.214970 11.00000 -1.50000 AFIX 0 C33 1 0.755264 -0.210035 0.292313 11.00000 0.05275 0.15098 = 0.16274 -0.07834 0.00095 0.01238 AFIX 137 H33A 2 0.763879 -0.232951 0.323948 11.00000 -1.50000 H33B 2 0.768039 -0.116194 0.288572 11.00000 -1.50000 H33C 2 0.814759 -0.258034 0.274903 11.00000 -1.50000 AFIX 0 HKLF 4 REM MM_8_2_0ma_a.res in P2(1)/c REM wR2 = 0.3022, GooF = S = 1.031, Restrained GooF = 1.031 for all data REM R1 = 0.0868 for 3980 Fo > 4sig(Fo) and 0.1355 for all 6640 data REM 348 parameters refined using 0 restraints END WGHT 0.1394 2.4674 REM Instructions for potential hydrogen bonds HTAB O1 N7 HTAB O2 N1 REM Highest difference peak 0.713, deepest hole -0.277, 1-sigma level 0.059 Q1 1 0.0429 1.1451 0.5323 11.00000 0.05 0.71 Q2 1 0.2625 1.1931 0.5074 11.00000 0.05 0.55 Q3 1 0.2978 0.5436 0.4407 11.00000 0.05 0.55 Q4 1 0.3516 0.5090 0.3994 11.00000 0.05 0.47 Q5 1 0.2445 1.1541 0.5822 11.00000 0.05 0.42 Q6 1 0.2851 0.6668 0.4441 11.00000 0.05 0.33 Q7 1 0.5056 0.4432 0.4141 11.00000 0.05 0.24 Q8 1 0.6737 -0.3432 0.3094 11.00000 0.05 0.23 Q9 1 0.7350 -0.0938 0.2593 11.00000 0.05 0.18 Q10 1 0.2083 1.1014 0.6152 11.00000 0.05 0.18 ; _shelx_res_checksum 21390 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' '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_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 O1 O 0.2445(3) 0.5485(2) 0.52407(9) 0.0827(8) Uani 1 1 d . . . . . H1 H 0.289844 0.531658 0.502705 0.124 Uiso 1 1 calc GR . . . . O2 O 0.2440(2) 0.0285(3) 0.36602(10) 0.0837(8) Uani 1 1 d . . . . . H2 H 0.272685 0.091700 0.380191 0.126 Uiso 1 1 calc GR . . . . N1 N 0.4072(3) 0.1884(3) 0.39916(10) 0.0741(8) Uani 1 1 d . . . . . C2 C 0.5510(3) -0.0669(3) 0.33066(10) 0.0528(7) Uani 1 1 d . . . . . H2A H 0.631592 -0.040599 0.335931 0.063 Uiso 1 1 calc R . . . . C1 C 0.3292(6) 1.1678(5) 0.5445(2) 0.144(3) Uani 1 1 d . . . . . H1A H 0.364102 1.130606 0.571823 0.216 Uiso 1 1 calc GR . . . . H1B H 0.324833 1.262766 0.547363 0.216 Uiso 1 1 calc GR . . . . H1C H 0.379448 1.145080 0.518981 0.216 Uiso 1 1 calc GR . . . . C34 C 0.1989(4) 1.1111(3) 0.53699(13) 0.0725(10) Uani 1 1 d . . . . . C3 C 0.2089(3) 0.9600(3) 0.53334(11) 0.0592(8) Uani 1 1 d . . . . . C4 C 0.2708(3) 0.9023(3) 0.49825(11) 0.0639(8) Uani 1 1 d . . . . . H4 H 0.305884 0.956393 0.476225 0.077 Uiso 1 1 calc R . . . . C5 C 0.2827(3) 0.7662(3) 0.49449(11) 0.0631(8) Uani 1 1 d . . . . . C6 C 0.3539(4) 0.7146(4) 0.45703(12) 0.0754(10) Uani 1 1 d . . . . . H6 H 0.381741 0.774264 0.435233 0.091 Uiso 1 1 calc R . . . . N7 N 0.3806(3) 0.5925(3) 0.45227(11) 0.0821(10) Uani 1 1 d . . . . . C8 C 0.4590(5) 0.5561(4) 0.41378(15) 0.0959(14) Uani 1 1 d . . . . . H8A H 0.454513 0.625241 0.390770 0.115 Uiso 1 1 calc R . . . . H8B H 0.543361 0.549866 0.424266 0.115 Uiso 1 1 calc R . . . . C9 C 0.4219(5) 0.4287(4) 0.39343(14) 0.0919(13) Uani 1 1 d . . . . . H9A H 0.464030 0.417970 0.364698 0.110 Uiso 1 1 calc R . . . . H9B H 0.334684 0.431829 0.386813 0.110 Uiso 1 1 calc R . . . . C10 C 0.4479(4) 0.3092(4) 0.42273(13) 0.0828(11) Uani 1 1 d . . . . . H10A H 0.535076 0.303701 0.429205 0.099 Uiso 1 1 calc R . . . . H10B H 0.405294 0.317729 0.451453 0.099 Uiso 1 1 calc R . . . . C11 C 0.4882(3) 0.1153(3) 0.38078(11) 0.0631(8) Uani 1 1 d . . . . . H11 H 0.570447 0.135743 0.385636 0.076 Uiso 1 1 calc R . . . . C12 C 0.4573(3) 0.0008(3) 0.35247(10) 0.0546(7) Uani 1 1 d . . . . . C13 C 0.3351(3) -0.0378(3) 0.34516(11) 0.0573(8) Uani 1 1 d . . . . . C14 C 0.3075(3) -0.1449(3) 0.31584(11) 0.0579(8) Uani 1 1 d . . . . . C15 C 0.1745(3) -0.1898(4) 0.30696(15) 0.0788(11) Uani 1 1 d . . . . . C16 C 0.1205(5) -0.2380(6) 0.3519(2) 0.129(2) Uani 1 1 d . . . . . H16A H 0.167846 -0.311558 0.363246 0.193 Uiso 1 1 calc GR . . . . H16B H 0.037302 -0.265877 0.346887 0.193 Uiso 1 1 calc GR . . . . H16C H 0.122407 -0.166895 0.373706 0.193 Uiso 1 1 calc GR . . . . C17 C 0.6117(4) -0.3964(4) 0.28182(18) 0.0965(14) Uani 1 1 d . . . . . H17A H 0.619431 -0.418584 0.313544 0.145 Uiso 1 1 calc GR . . . . H17B H 0.673559 -0.442280 0.264911 0.145 Uiso 1 1 calc GR . . . . H17C H 0.532116 -0.422415 0.270820 0.145 Uiso 1 1 calc GR . . . . C18 C 0.6276(3) -0.2462(3) 0.27576(11) 0.0598(8) Uani 1 1 d . . . . . C19 C 0.5284(3) -0.1717(3) 0.30146(10) 0.0509(7) Uani 1 1 d . . . . . C20 C 0.4057(3) -0.2065(3) 0.29535(11) 0.0559(7) Uani 1 1 d . . . . . H20 H 0.388491 -0.277175 0.275849 0.067 Uiso 1 1 calc R . . . . C21 C 0.0990(4) -0.0740(5) 0.2869(2) 0.1157(18) Uani 1 1 d . . . . . H21A H 0.100181 -0.000531 0.307769 0.174 Uiso 1 1 calc GR . . . . H21B H 0.016024 -0.102483 0.281872 0.174 Uiso 1 1 calc GR . . . . H21C H 0.133873 -0.046792 0.258423 0.174 Uiso 1 1 calc GR . . . . C22 C 0.1684(4) -0.3052(6) 0.2730(2) 0.130(2) Uani 1 1 d . . . . . H22A H 0.204798 -0.278582 0.244814 0.195 Uiso 1 1 calc GR . . . . H22B H 0.084310 -0.329371 0.267708 0.195 Uiso 1 1 calc GR . . . . H22C H 0.212090 -0.380217 0.285278 0.195 Uiso 1 1 calc GR . . . . C23 C 0.2291(3) 0.6823(3) 0.52730(11) 0.0611(8) Uani 1 1 d . . . . . C24 C 0.1627(3) 0.7360(3) 0.56333(11) 0.0590(8) Uani 1 1 d . . . . . C25 C 0.0988(4) 0.6486(4) 0.59867(13) 0.0779(11) Uani 1 1 d . . . . . C26 C 0.1948(5) 0.5674(5) 0.62525(16) 0.1070(17) Uani 1 1 d . . . . . H26A H 0.235573 0.507781 0.604837 0.160 Uiso 1 1 calc GR . . . . H26B H 0.155095 0.517168 0.648696 0.160 Uiso 1 1 calc GR . . . . H26C H 0.253736 0.626577 0.638856 0.160 Uiso 1 1 calc GR . . . . C27 C 0.0088(5) 0.5532(5) 0.5745(2) 0.1103(17) Uani 1 1 d . . . . . H27A H -0.052379 0.603759 0.558441 0.165 Uiso 1 1 calc GR . . . . H27B H -0.029986 0.497642 0.596782 0.165 Uiso 1 1 calc GR . . . . H27C H 0.052703 0.498605 0.553383 0.165 Uiso 1 1 calc GR . . . . C28 C 0.0282(5) 0.7317(5) 0.63330(17) 0.117(2) Uani 1 1 d . . . . . H28A H 0.083944 0.789449 0.649276 0.176 Uiso 1 1 calc GR . . . . H28B H -0.011125 0.673731 0.654670 0.176 Uiso 1 1 calc GR . . . . H28C H -0.032668 0.784108 0.617704 0.176 Uiso 1 1 calc GR . . . . C29 C 0.1564(3) 0.8738(3) 0.56497(10) 0.0596(8) Uani 1 1 d . . . . . H29 H 0.113842 0.911774 0.589012 0.072 Uiso 1 1 calc R . . . . C30 C 0.1568(7) 1.1692(5) 0.4928(2) 0.132(2) Uani 1 1 d . . . . . H30A H 0.166420 1.264083 0.493619 0.198 Uiso 1 1 calc GR . . . . H30B H 0.072094 1.147580 0.487720 0.198 Uiso 1 1 calc GR . . . . H30C H 0.204924 1.133259 0.468440 0.198 Uiso 1 1 calc GR . . . . C31A C 0.1266(10) 1.1526(5) 0.5765(3) 0.218(5) Uani 1 1 d . . . A 1 H31A H 0.147487 1.097931 0.602261 0.327 Uiso 1 1 calc GR . . A 1 H31B H 0.040892 1.142940 0.569547 0.327 Uiso 1 1 calc GR . . A 1 H31C H 0.144067 1.243940 0.583517 0.327 Uiso 1 1 calc GR . . A 1 C32 C 0.6161(5) -0.2159(6) 0.22521(14) 0.1029(15) Uani 1 1 d . . . . . H32A H 0.673032 -0.269825 0.208653 0.154 Uiso 1 1 calc GR . . . . H32B H 0.633790 -0.123627 0.220045 0.154 Uiso 1 1 calc GR . . . . H32C H 0.534170 -0.235146 0.214970 0.154 Uiso 1 1 calc GR . . . . C33 C 0.7553(4) -0.2100(6) 0.2923(2) 0.122(2) Uani 1 1 d . . . . . H33A H 0.763879 -0.232951 0.323948 0.183 Uiso 1 1 calc GR . . . . H33B H 0.768039 -0.116194 0.288572 0.183 Uiso 1 1 calc GR . . . . H33C H 0.814759 -0.258034 0.274903 0.183 Uiso 1 1 calc 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 0.122(2) 0.0487(13) 0.0780(17) 0.0086(11) 0.0225(15) 0.0172(13) O2 0.0656(15) 0.0879(19) 0.098(2) -0.0190(15) 0.0264(14) 0.0067(13) N1 0.093(2) 0.0628(17) 0.0661(18) -0.0152(14) 0.0077(16) 0.0098(16) C2 0.0468(16) 0.0552(17) 0.0564(17) -0.0033(13) -0.0040(13) 0.0041(13) C1 0.171(6) 0.082(3) 0.178(6) 0.015(4) -0.062(5) -0.030(4) C34 0.098(3) 0.0482(18) 0.071(2) -0.0006(16) -0.009(2) 0.0012(17) C3 0.071(2) 0.0500(17) 0.0570(18) 0.0020(14) 0.0008(15) 0.0033(14) C4 0.079(2) 0.0537(18) 0.0594(18) 0.0076(14) 0.0079(16) 0.0050(16) C5 0.076(2) 0.0564(18) 0.0571(18) 0.0056(14) 0.0070(16) 0.0121(16) C6 0.099(3) 0.064(2) 0.064(2) 0.0035(17) 0.0164(19) 0.0100(19) N7 0.114(3) 0.0632(19) 0.0696(19) -0.0057(15) 0.0220(18) 0.0100(17) C8 0.124(4) 0.079(3) 0.085(3) -0.015(2) 0.035(3) -0.002(2) C9 0.136(4) 0.072(2) 0.068(2) -0.0129(19) 0.026(2) 0.002(2) C10 0.115(3) 0.064(2) 0.070(2) -0.0191(18) 0.007(2) 0.002(2) C11 0.074(2) 0.0565(18) 0.0584(18) -0.0047(15) -0.0043(16) 0.0057(16) C12 0.0615(19) 0.0514(16) 0.0509(16) -0.0020(13) 0.0017(13) 0.0048(14) C13 0.0565(18) 0.0566(17) 0.0589(18) 0.0047(14) 0.0134(14) 0.0052(14) C14 0.0502(17) 0.0565(17) 0.0672(19) 0.0022(15) 0.0075(14) -0.0052(13) C15 0.0498(19) 0.079(2) 0.108(3) -0.001(2) 0.0080(19) -0.0128(17) C16 0.091(3) 0.138(5) 0.158(5) 0.022(4) 0.042(3) -0.043(3) C17 0.097(3) 0.068(2) 0.125(4) -0.002(2) 0.019(3) 0.023(2) C18 0.0524(18) 0.0643(19) 0.0629(19) -0.0094(15) 0.0049(14) 0.0050(14) C19 0.0494(16) 0.0524(16) 0.0509(16) -0.0003(13) 0.0012(12) 0.0022(13) C20 0.0556(18) 0.0531(17) 0.0590(17) -0.0026(14) 0.0010(14) -0.0029(13) C21 0.055(2) 0.116(4) 0.175(5) 0.015(4) -0.020(3) -0.010(2) C22 0.067(3) 0.132(4) 0.190(6) -0.061(4) -0.009(3) -0.030(3) C23 0.076(2) 0.0471(16) 0.0599(18) 0.0062(14) 0.0037(16) 0.0117(15) C24 0.068(2) 0.0532(17) 0.0557(17) 0.0105(14) 0.0052(15) 0.0097(14) C25 0.087(3) 0.071(2) 0.077(2) 0.0282(19) 0.022(2) 0.021(2) C26 0.126(4) 0.112(4) 0.084(3) 0.049(3) 0.023(3) 0.043(3) C27 0.102(3) 0.088(3) 0.141(4) 0.042(3) 0.022(3) -0.009(3) C28 0.140(4) 0.108(4) 0.105(3) 0.040(3) 0.065(3) 0.042(3) C29 0.070(2) 0.0580(18) 0.0505(17) 0.0010(14) 0.0030(15) 0.0100(15) C30 0.200(6) 0.065(3) 0.130(4) 0.009(3) -0.034(4) 0.032(3) C31A 0.401(14) 0.058(3) 0.199(8) -0.012(4) 0.163(9) 0.022(5) C32 0.111(4) 0.124(4) 0.074(3) -0.007(3) 0.020(2) 0.026(3) C33 0.053(2) 0.151(5) 0.163(5) -0.078(4) 0.001(3) 0.012(3) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 N1 C10 118.0(4) . . ? C19 C2 C12 122.2(3) . . ? C3 C34 C1 108.1(4) . . ? C30 C34 C1 104.8(4) . . ? C30 C34 C3 110.5(3) . . ? C31A C34 C1 106.5(6) . . ? C31A C34 C3 112.1(4) . . ? C31A C34 C30 114.3(5) . . ? C4 C3 C34 120.8(3) . . ? C4 C3 C29 116.5(3) . . ? C29 C3 C34 122.7(3) . . ? C3 C4 C5 122.0(3) . . ? C4 C5 C6 117.9(3) . . ? C4 C5 C23 119.9(3) . . ? C23 C5 C6 122.2(3) . . ? N7 C6 C5 123.7(3) . . ? C6 N7 C8 117.5(3) . . ? C9 C8 N7 111.7(4) . . ? C8 C9 C10 114.5(4) . . ? N1 C10 C9 109.7(3) . . ? N1 C11 C12 122.6(3) . . ? C2 C12 C11 118.8(3) . . ? C2 C12 C13 119.8(3) . . ? C13 C12 C11 121.3(3) . . ? O2 C13 C12 119.8(3) . . ? O2 C13 C14 120.1(3) . . ? C12 C13 C14 120.1(3) . . ? C13 C14 C15 121.5(3) . . ? C20 C14 C13 116.6(3) . . ? C20 C14 C15 121.9(3) . . ? C16 C15 C14 108.5(4) . . ? C16 C15 C21 111.1(4) . . ? C16 C15 C22 107.8(4) . . ? C21 C15 C14 110.0(3) . . ? C22 C15 C14 111.6(3) . . ? C22 C15 C21 107.7(4) . . ? C19 C18 C17 110.2(3) . . ? C32 C18 C17 107.6(4) . . ? C32 C18 C19 109.4(3) . . ? C33 C18 C17 107.7(4) . . ? C33 C18 C19 112.3(3) . . ? C33 C18 C32 109.4(4) . . ? C2 C19 C18 124.1(3) . . ? C2 C19 C20 115.9(3) . . ? C20 C19 C18 120.0(3) . . ? C14 C20 C19 125.4(3) . . ? O1 C23 C5 119.5(3) . . ? O1 C23 C24 120.1(3) . . ? C24 C23 C5 120.4(3) . . ? C23 C24 C25 122.2(3) . . ? C29 C24 C23 116.0(3) . . ? C29 C24 C25 121.7(3) . . ? C24 C25 C26 109.6(3) . . ? C24 C25 C27 109.8(3) . . ? C26 C25 C27 109.3(4) . . ? C28 C25 C24 111.9(3) . . ? C28 C25 C26 107.4(4) . . ? C28 C25 C27 108.8(4) . . ? C24 C29 C3 125.1(3) . . ? 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 O1 C23 1.359(4) . ? O2 C13 1.349(4) . ? N1 C10 1.464(5) . ? N1 C11 1.274(4) . ? C2 C12 1.389(4) . ? C2 C19 1.379(4) . ? C1 C34 1.545(7) . ? C34 C3 1.527(5) . ? C34 C30 1.492(6) . ? C34 C31A 1.469(7) . ? C3 C4 1.366(5) . ? C3 C29 1.397(4) . ? C4 C5 1.379(5) . ? C5 C6 1.449(5) . ? C5 C23 1.411(5) . ? C6 N7 1.269(5) . ? N7 C8 1.470(5) . ? C8 C9 1.468(6) . ? C9 C10 1.503(6) . ? C11 C12 1.457(4) . ? C12 C13 1.404(4) . ? C13 C14 1.408(5) . ? C14 C15 1.540(5) . ? C14 C20 1.380(4) . ? C15 C16 1.528(6) . ? C15 C21 1.540(6) . ? C15 C22 1.530(6) . ? C17 C18 1.530(5) . ? C18 C19 1.522(4) . ? C18 C32 1.518(5) . ? C18 C33 1.515(5) . ? C19 C20 1.394(4) . ? C23 C24 1.396(4) . ? C24 C25 1.532(5) . ? C24 C29 1.388(4) . ? C25 C26 1.535(5) . ? C25 C27 1.540(7) . ? C25 C28 1.529(6) . ? 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 O1 C23 C24 C25 -3.6(5) . . . . ? O1 C23 C24 C29 177.2(3) . . . . ? O2 C13 C14 C15 -0.4(5) . . . . ? O2 C13 C14 C20 179.2(3) . . . . ? N1 C11 C12 C2 174.6(3) . . . . ? N1 C11 C12 C13 -2.2(5) . . . . ? C2 C12 C13 O2 -179.4(3) . . . . ? C2 C12 C13 C14 0.1(5) . . . . ? C2 C19 C20 C14 0.2(5) . . . . ? C1 C34 C3 C4 -64.2(5) . . . . ? C1 C34 C3 C29 115.9(4) . . . . ? C34 C3 C4 C5 179.1(3) . . . . ? C34 C3 C29 C24 -180.0(3) . . . . ? C3 C4 C5 C6 -177.7(3) . . . . ? C3 C4 C5 C23 0.6(6) . . . . ? C4 C3 C29 C24 0.1(5) . . . . ? C4 C5 C6 N7 173.5(4) . . . . ? C4 C5 C23 O1 -178.0(3) . . . . ? C4 C5 C23 C24 0.8(5) . . . . ? C5 C6 N7 C8 -176.9(4) . . . . ? C5 C23 C24 C25 177.5(3) . . . . ? C5 C23 C24 C29 -1.6(5) . . . . ? C6 C5 C23 O1 0.1(6) . . . . ? C6 C5 C23 C24 179.0(3) . . . . ? C6 N7 C8 C9 -142.6(4) . . . . ? N7 C8 C9 C10 -70.3(6) . . . . ? C8 C9 C10 N1 179.9(4) . . . . ? C10 N1 C11 C12 -173.4(3) . . . . ? C11 N1 C10 C9 103.1(4) . . . . ? C11 C12 C13 O2 -2.6(5) . . . . ? C11 C12 C13 C14 176.9(3) . . . . ? C12 C2 C19 C18 178.2(3) . . . . ? C12 C2 C19 C20 -0.4(4) . . . . ? C12 C13 C14 C15 -179.9(3) . . . . ? C12 C13 C14 C20 -0.3(5) . . . . ? C13 C14 C15 C16 -62.8(5) . . . . ? C13 C14 C15 C21 59.0(5) . . . . ? C13 C14 C15 C22 178.5(4) . . . . ? C13 C14 C20 C19 0.2(5) . . . . ? C15 C14 C20 C19 179.8(3) . . . . ? C17 C18 C19 C2 130.8(4) . . . . ? C17 C18 C19 C20 -50.6(4) . . . . ? C18 C19 C20 C14 -178.5(3) . . . . ? C19 C2 C12 C11 -176.5(3) . . . . ? C19 C2 C12 C13 0.3(5) . . . . ? C20 C14 C15 C16 117.6(4) . . . . ? C20 C14 C15 C21 -120.6(4) . . . . ? C20 C14 C15 C22 -1.1(6) . . . . ? C23 C5 C6 N7 -4.7(6) . . . . ? C23 C24 C25 C26 63.4(5) . . . . ? C23 C24 C25 C27 -56.7(5) . . . . ? C23 C24 C25 C28 -177.7(4) . . . . ? C23 C24 C29 C3 1.1(5) . . . . ? C25 C24 C29 C3 -178.0(3) . . . . ? C29 C3 C4 C5 -1.0(5) . . . . ? C29 C24 C25 C26 -117.5(4) . . . . ? C29 C24 C25 C27 122.3(4) . . . . ? C29 C24 C25 C28 1.4(6) . . . . ? C30 C34 C3 C4 49.9(6) . . . . ? C30 C34 C3 C29 -130.0(5) . . . . ? C31A C34 C3 C4 178.7(6) . . . . ? C31A C34 C3 C29 -1.2(7) . . . . ? C32 C18 C19 C2 -111.0(4) . . . . ? C32 C18 C19 C20 67.6(4) . . . . ? C33 C18 C19 C2 10.7(5) . . . . ? C33 C18 C19 C20 -170.8(4) . . . . ?