#------------------------------------------------------------------------------ #$Date: 2019-11-10 18:52:15 +0200 (Sun, 10 Nov 2019) $ #$Revision: 225955 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/51/58/4515855.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_4515855 loop_ _publ_author_name 'Gupta, Abhishek Kumar' 'Kumar, Ashwani' 'Singh, Ranjit' 'Devi, Manisha' 'Dhir, Abhimanew' 'Pradeep, Chullikkattil P.' _publ_section_title ; Facile Synthesis of an Organic Solid State Near-Infrared-Emitter with Large Stokes Shift via Excited-State Intramolecular Proton Transfer. ; _journal_issue 10 _journal_name_full 'ACS omega' _journal_page_first 14341 _journal_page_last 14348 _journal_paper_doi 10.1021/acsomega.8b02116 _journal_volume 3 _journal_year 2018 _chemical_formula_moiety '2(C23 H22 N2 O2 S2)' _chemical_formula_sum 'C46 H44 N4 O4 S4' _chemical_formula_weight 845.09 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap _audit_creation_date 2017-05-29 _audit_creation_method ; Olex2 1.2-ac21 (compiled 2015.09.16 svn.r134, GUI svn.r4998) ; _cell_angle_alpha 93.055(3) _cell_angle_beta 107.510(4) _cell_angle_gamma 106.789(4) _cell_formula_units_Z 2 _cell_length_a 10.0414(4) _cell_length_b 15.0433(6) _cell_length_c 15.5315(6) _cell_measurement_reflns_used 6400 _cell_measurement_temperature 300 _cell_measurement_theta_max 66.7130 _cell_measurement_theta_min 3.0120 _cell_volume 2116.64(16) _computing_cell_refinement 'CrysAlisPro 1.171.38.43i (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43i (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43i (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution ; Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008; Palatinus et al., 2012) ; _diffrn_ambient_temperature 300 _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 7.9987 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.980 _diffrn_measured_fraction_theta_max 0.980 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames -------------------------------------------------------------------------- 1 \w -6.00 88.00 1.00 1.00 -- 25.44 57.00 30.00 94 2 \w 101.00 132.00 1.00 2.00 -- 66.72 63.00 -90.00 31 3 \w 100.00 135.00 1.00 2.00 -- 66.72 111.00-150.00 35 4 \w 108.00 145.00 1.00 2.00 -- 66.72 111.00-120.00 37 5 \w 96.00 175.00 1.00 10.00 -- 108.00 32.00-150.00 79 6 \w 119.00 175.00 1.00 10.00 -- 108.00 138.00 30.00 56 7 \w 110.00 175.00 1.00 10.00 -- 108.00 65.00 150.00 65 8 \w 112.00 178.00 1.00 10.00 -- 108.00 104.00 120.00 66 9 \w 75.00 145.00 1.00 2.00 -- 66.72 12.00 -90.00 70 10 \w 82.00 164.00 1.00 10.00 -- 108.00 65.00 -90.00 82 11 \w 65.00 138.00 1.00 2.00 -- 66.72 178.00 -90.00 73 12 \w 67.00 172.00 1.00 10.00 -- 108.00 77.00 -60.00 105 13 \w 69.00 178.00 1.00 10.00 -- 108.00 54.00-120.00 109 14 \w 117.00 143.00 1.00 10.00 -- 108.00 -65.00 60.00 26 15 \w 66.00 112.00 1.00 10.00 -- 108.00-104.00 90.00 46 16 \w 61.00 138.00 1.00 10.00 -- 108.00 -65.00 120.00 77 17 \w 73.00 99.00 1.00 10.00 -- 108.00 65.00 150.00 26 18 \w 31.00 101.00 1.00 10.00 -- 108.00 -65.00 60.00 70 19 \w 37.00 118.00 1.00 10.00 -- 108.00-117.00 -29.91 81 20 \w 73.00 109.00 1.00 10.00 -- 108.00-104.00-180.00 36 21 \w 28.00 57.00 1.00 10.00 -- 108.00-104.00-180.00 29 22 \w 19.00 83.00 1.00 2.00 -- 66.72-111.00-120.00 64 23 \w 28.00 93.00 1.00 10.00 -- 108.00-104.00 0.00 65 24 \w 23.00 56.00 1.00 10.00 -- 108.00-104.00 90.00 33 25 \w 23.00 101.00 1.00 10.00 -- 108.00-104.00 60.00 78 26 \w 7.00 116.00 1.00 2.00 -- 66.72 -38.00 -90.00 109 27 \w 41.00 67.00 1.00 2.00 -- 66.72 63.00 -90.00 26 28 \w -9.00 95.00 1.00 1.00 -- 25.44 57.00 -90.00 104 29 \w -10.00 100.00 1.00 1.00 -- 25.44 57.00 150.00 110 30 \w 1.00 117.00 1.00 2.00 -- 66.72 -91.00 -60.00 116 31 \w -14.00 72.00 1.00 2.00 -- 66.72 12.00 -90.00 86 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0460423000 _diffrn_orient_matrix_UB_12 0.0932978000 _diffrn_orient_matrix_UB_13 -0.0365299000 _diffrn_orient_matrix_UB_21 -0.1399184000 _diffrn_orient_matrix_UB_22 0.0196063000 _diffrn_orient_matrix_UB_23 0.0052470000 _diffrn_orient_matrix_UB_31 0.0844936000 _diffrn_orient_matrix_UB_32 0.0512802000 _diffrn_orient_matrix_UB_33 0.0985754000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_unetI/netI 0.0423 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 12596 _diffrn_reflns_theta_full 66.97 _diffrn_reflns_theta_max 66.97 _diffrn_reflns_theta_min 3.02 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.452 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.475 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details 'CrysAlisPro 1.171.38.43i (Rigaku Oxford Diffraction, 2015) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.' _exptl_crystal_colour 'metallic dark red' _exptl_crystal_colour_lustre metallic _exptl_crystal_colour_modifier dark _exptl_crystal_colour_primary red _exptl_crystal_density_diffrn 1.326 _exptl_crystal_density_method 'not measured' _exptl_crystal_description triclinic _exptl_crystal_F_000 888 _exptl_crystal_size_max 0.245 _exptl_crystal_size_mid 0.181 _exptl_crystal_size_min 0.084 _refine_diff_density_max 0.314 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.046 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 531 _refine_ls_number_reflns 7383 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.139 _refine_ls_R_factor_all 0.0606 _refine_ls_R_factor_gt 0.0495 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0668P)^2^+1.0115P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1576 _refine_ls_wR_factor_ref 0.1652 _reflns_number_gt 6129 _reflns_number_total 7383 _reflns_threshold_expression >2sigma(I) _cod_data_source_file ao8b02116_si_003.cif _cod_data_source_block sbl_126_rt_cu _cod_original_cell_volume 2116.64(15) _cod_database_code 4515855 _chemical_oxdiff_formula 'C92 H88 N8 O8 S8' _reflns_odcompleteness_completeness 97.75 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Aromatic/amide H refined with riding coordinates: C26(H26), C6(H6), C25(H25), C28(H28), C29(H29), C7(H7), C4(H4), C37(H37), C15(H15), C21(H21), C8(H8), C20(H20), C3(H3), C39(H39), C34(H34), C30(H30), C12(H12), C40(H40), C43(H43), C17(H17), C10(H10), C42(H42), C32(H32), C18(H18) 2.b Idealised Me refined as rotating group: C23(H23A,H23B,H23C), C1(H1A,H1B,H1C), C46(H46A,H46B,H46C), C45(H45A,H45B, H45C), C44(H44A,H44B,H44C), C22(H22A,H22B,H22C) 2.c Idealised tetrahedral OH refined as rotating group: O2(H2), O4(H4A) ; _olex2_date_sample_data_collection 2016-04-11 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.842 _oxdiff_exptl_absorpt_empirical_full_min 0.211 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-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_calc_flag _atom_site_refinement_flags_posn S1 S 0.73460(13) 0.40722(5) 0.34795(9) 0.0839(3) Uani 1 d . S3 S 0.24488(11) 0.40115(5) 0.30834(7) 0.0706(3) Uani 1 d . S4 S 1.04628(10) 1.38145(6) -0.03362(6) 0.0667(2) Uani 1 d . S2 S 1.50052(13) 1.29431(8) -0.10423(7) 0.0822(3) Uani 1 d . O2 O 1.0520(2) 0.95416(13) 0.18601(14) 0.0529(5) Uani 1 d . H2 H 1.0980 0.9887 0.1584 0.079 Uiso 1 calc GR O4 O 0.5317(3) 0.96861(14) 0.17906(16) 0.0609(5) Uani 1 d . H4A H 0.5732 1.0066 0.1519 0.091 Uiso 1 calc GR O3 O 0.3646(3) 1.15986(13) 0.41887(15) 0.0583(5) Uani 1 d . O1 O 0.8680(3) 1.16688(13) 0.39786(16) 0.0602(5) Uani 1 d . C23 C 0.2961(5) 0.3740(3) 0.4210(3) 0.0961(15) Uani 1 d . H23A H 0.2902 0.3090 0.4185 0.144 Uiso 1 calc GR H23B H 0.2306 0.3856 0.4509 0.144 Uiso 1 calc GR H23C H 0.3953 0.4126 0.4544 0.144 Uiso 1 calc GR C26 C 0.3305(3) 0.67457(19) 0.4100(2) 0.0492(6) Uani 1 d . H26 H 0.3557 0.7114 0.4661 0.059 Uiso 1 calc R N4 N 0.6479(3) 1.13492(17) 0.13754(16) 0.0518(5) Uani 1 d . N2 N 1.1567(3) 1.10939(16) 0.12637(16) 0.0501(5) Uani 1 d . N3 N 0.3358(3) 0.81422(15) 0.34045(17) 0.0488(5) Uani 1 d . N1 N 0.8314(3) 0.81690(15) 0.34331(17) 0.0490(5) Uani 1 d . C1 C 0.9102(6) 0.3928(3) 0.3878(3) 0.1013(15) Uani 1 d . H1A H 0.9594 0.4083 0.3437 0.152 Uiso 1 calc GR H1B H 0.8992 0.3287 0.3965 0.152 Uiso 1 calc GR H1C H 0.9674 0.4335 0.4448 0.152 Uiso 1 calc GR C6 C 0.9294(3) 0.68470(18) 0.3494(2) 0.0486(6) Uani 1 d . H6 H 1.0211 0.7249 0.3524 0.058 Uiso 1 calc R C25 C 0.3106(3) 0.57906(19) 0.4062(2) 0.0516(6) Uani 1 d . H25 H 0.3245 0.5526 0.4597 0.062 Uiso 1 calc R C28 C 0.2697(3) 0.65912(19) 0.2480(2) 0.0486(6) Uani 1 d . H28 H 0.2547 0.6853 0.1943 0.058 Uiso 1 calc R C29 C 0.2482(3) 0.56403(19) 0.2441(2) 0.0516(6) Uani 1 d . H29 H 0.2186 0.5268 0.1877 0.062 Uiso 1 calc R C7 C 0.9093(3) 0.58969(19) 0.3509(2) 0.0527(7) Uani 1 d . H7 H 0.9873 0.5668 0.3553 0.063 Uiso 1 calc R C14 C 1.0045(3) 1.00527(17) 0.23723(18) 0.0428(5) Uani 1 d . C36 C 0.4901(3) 1.01393(18) 0.23840(18) 0.0455(6) Uani 1 d . C4 C 0.6791(3) 0.6594(2) 0.3397(2) 0.0555(7) Uani 1 d . H4 H 0.6018 0.6826 0.3371 0.067 Uiso 1 calc R C46 C 0.2997(4) 1.1146(2) 0.4807(2) 0.0592(7) Uani 1 d . H46A H 0.2094 1.0659 0.4472 0.089 Uiso 1 calc GR H46B H 0.2794 1.1596 0.5168 0.089 Uiso 1 calc GR H46C H 0.3662 1.0876 0.5200 0.089 Uiso 1 calc GR C5 C 0.8155(3) 0.72042(17) 0.34359(18) 0.0441(6) Uani 1 d . C13 C 1.0286(3) 1.10234(17) 0.23373(18) 0.0438(6) Uani 1 d . C37 C 0.5981(3) 1.16905(19) 0.19342(19) 0.0490(6) Uani 1 d . H37 H 0.6139 1.2334 0.2010 0.059 Uiso 1 calc R C15 C 1.1042(3) 1.15097(18) 0.17576(19) 0.0482(6) Uani 1 d . H15 H 1.1152 1.2144 0.1743 0.058 Uiso 1 calc R C16 C 1.2390(3) 1.15907(19) 0.07496(19) 0.0483(6) Uani 1 d . C21 C 1.2457(4) 1.1086(2) -0.0006(2) 0.0567(7) Uani 1 d . H21 H 1.1951 1.0445 -0.0155 0.068 Uiso 1 calc R C45 C 0.8032(4) 1.1272(2) 0.4622(2) 0.0580(7) Uani 1 d . H45A H 0.7139 1.0768 0.4309 0.087 Uiso 1 calc GR H45B H 0.7814 1.1745 0.4942 0.087 Uiso 1 calc GR H45C H 0.8706 1.1034 0.5049 0.087 Uiso 1 calc GR C9 C 0.9297(3) 0.96183(17) 0.29363(18) 0.0431(6) Uani 1 d . C27 C 0.3137(3) 0.71611(17) 0.33153(19) 0.0439(6) Uani 1 d . C35 C 0.5182(3) 1.11219(18) 0.24563(18) 0.0454(6) Uani 1 d . C24 C 0.2698(3) 0.52288(18) 0.3227(2) 0.0492(6) Uani 1 d . C8 C 0.9026(3) 0.86097(17) 0.29611(19) 0.0467(6) Uani 1 d . H8 H 0.9395 0.8284 0.2614 0.056 Uiso 1 calc R C31 C 0.4194(3) 0.96369(18) 0.29387(19) 0.0451(6) Uani 1 d . C20 C 1.3252(4) 1.1515(2) -0.0534(2) 0.0596(7) Uani 1 d . H20 H 1.3266 1.1167 -0.1042 0.072 Uiso 1 calc R C38 C 0.7366(3) 1.1953(2) 0.09479(19) 0.0496(6) Uani 1 d . C3 C 0.6584(3) 0.5648(2) 0.3398(2) 0.0603(8) Uani 1 d . H3 H 0.5662 0.5245 0.3356 0.072 Uiso 1 calc R C39 C 0.8080(4) 1.2914(2) 0.1264(2) 0.0608(8) Uani 1 d . H39 H 0.7935 1.3194 0.1761 0.073 Uiso 1 calc R C34 C 0.4733(3) 1.15641(18) 0.30686(19) 0.0478(6) Uani 1 d . H34 H 0.4911 1.2210 0.3113 0.057 Uiso 1 calc R C2 C 0.7731(3) 0.52888(18) 0.3459(2) 0.0514(6) Uani 1 d . C30 C 0.3944(3) 0.86201(18) 0.2890(2) 0.0483(6) Uani 1 d . H30 H 0.4225 0.8319 0.2469 0.058 Uiso 1 calc R C12 C 0.9795(3) 1.15223(17) 0.2886(2) 0.0473(6) Uani 1 d . H12 H 0.9949 1.2159 0.2864 0.057 Uiso 1 calc R C40 C 0.8985(4) 1.3444(2) 0.0852(2) 0.0603(8) Uani 1 d . H40 H 0.9438 1.4083 0.1069 0.072 Uiso 1 calc R C33 C 0.4025(3) 1.10677(18) 0.36160(19) 0.0451(6) Uani 1 d . C43 C 0.7612(4) 1.1565(2) 0.0208(2) 0.0567(7) Uani 1 d . H43 H 0.7147 1.0928 -0.0014 0.068 Uiso 1 calc R C17 C 1.3198(3) 1.2543(2) 0.0976(2) 0.0548(7) Uani 1 d . H17 H 1.3187 1.2893 0.1485 0.066 Uiso 1 calc R C10 C 0.8829(3) 1.01409(17) 0.34847(19) 0.0456(6) Uani 1 d . H10 H 0.8343 0.9848 0.3867 0.055 Uiso 1 calc R C44 C 1.0672(4) 1.3048(3) -0.1169(3) 0.0773(10) Uani 1 d . H44A H 0.9743 1.2768 -0.1647 0.116 Uiso 1 calc GR H44B H 1.1002 1.2563 -0.0885 0.116 Uiso 1 calc GR H44C H 1.1385 1.3400 -0.1423 0.116 Uiso 1 calc GR C42 C 0.8532(4) 1.2098(2) -0.0210(2) 0.0577(7) Uani 1 d . H42 H 0.8675 1.1820 -0.0710 0.069 Uiso 1 calc R C41 C 0.9242(3) 1.3048(2) 0.01139(19) 0.0509(6) Uani 1 d . C22 C 1.5479(8) 1.4156(4) -0.0735(5) 0.140(3) Uani 1 d . H22A H 1.5899 1.4475 -0.1158 0.210 Uiso 1 calc GR H22B H 1.6185 1.4346 -0.0130 0.210 Uiso 1 calc GR H22C H 1.4612 1.4314 -0.0749 0.210 Uiso 1 calc GR C11 C 0.9085(3) 1.10930(17) 0.3463(2) 0.0460(6) Uani 1 d . C19 C 1.4036(3) 1.2468(2) -0.0313(2) 0.0548(7) Uani 1 d . C32 C 0.3762(3) 1.01071(18) 0.35532(19) 0.0456(6) Uani 1 d . H32 H 0.3294 0.9771 0.3924 0.055 Uiso 1 calc R C18 C 1.4014(4) 1.2973(2) 0.0452(2) 0.0584(7) Uani 1 d . H18 H 1.4556 1.3609 0.0614 0.070 Uiso 1 calc R 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 S1 0.1095(8) 0.0315(4) 0.1302(9) 0.0186(4) 0.0696(7) 0.0190(4) S3 0.0864(6) 0.0334(3) 0.0883(6) 0.0056(3) 0.0294(5) 0.0137(3) S4 0.0731(5) 0.0668(5) 0.0681(5) 0.0195(4) 0.0369(4) 0.0184(4) S2 0.1015(7) 0.0905(7) 0.0835(6) 0.0319(5) 0.0616(6) 0.0378(6) O2 0.0642(12) 0.0386(9) 0.0627(12) 0.0089(8) 0.0296(10) 0.0174(9) O4 0.0753(14) 0.0454(10) 0.0678(13) 0.0040(9) 0.0377(11) 0.0140(10) O3 0.0785(14) 0.0394(10) 0.0706(13) 0.0121(9) 0.0411(11) 0.0214(9) O1 0.0785(14) 0.0355(9) 0.0834(14) 0.0124(9) 0.0446(12) 0.0236(9) C23 0.108(3) 0.0497(19) 0.106(3) 0.019(2) -0.004(3) 0.030(2) C26 0.0530(15) 0.0400(13) 0.0556(15) 0.0061(11) 0.0189(13) 0.0159(11) N4 0.0533(13) 0.0493(13) 0.0479(12) 0.0096(10) 0.0145(11) 0.0112(10) N2 0.0521(13) 0.0434(12) 0.0547(13) 0.0124(10) 0.0176(11) 0.0145(10) N3 0.0518(13) 0.0353(11) 0.0633(14) 0.0104(10) 0.0216(11) 0.0167(9) N1 0.0585(14) 0.0333(11) 0.0631(14) 0.0128(10) 0.0269(11) 0.0184(9) C1 0.150(4) 0.050(2) 0.110(3) 0.018(2) 0.030(3) 0.055(2) C6 0.0479(15) 0.0355(12) 0.0662(17) 0.0122(11) 0.0242(13) 0.0126(11) C25 0.0535(16) 0.0413(14) 0.0603(16) 0.0125(12) 0.0179(13) 0.0159(12) C28 0.0466(14) 0.0428(13) 0.0543(15) 0.0094(11) 0.0167(12) 0.0109(11) C29 0.0500(15) 0.0414(14) 0.0576(16) 0.0006(12) 0.0170(13) 0.0081(11) C7 0.0568(16) 0.0390(13) 0.0735(18) 0.0149(12) 0.0293(14) 0.0225(12) C14 0.0416(13) 0.0352(12) 0.0482(13) 0.0050(10) 0.0102(11) 0.0124(10) C36 0.0440(14) 0.0400(13) 0.0494(14) 0.0039(11) 0.0128(11) 0.0121(10) C4 0.0511(16) 0.0447(14) 0.082(2) 0.0195(14) 0.0317(15) 0.0206(12) C46 0.0681(19) 0.0546(16) 0.0610(17) 0.0095(13) 0.0308(15) 0.0185(14) C5 0.0529(15) 0.0327(12) 0.0522(14) 0.0102(10) 0.0227(12) 0.0156(10) C13 0.0417(13) 0.0356(12) 0.0518(14) 0.0106(10) 0.0119(11) 0.0120(10) C37 0.0493(15) 0.0434(13) 0.0524(15) 0.0125(11) 0.0143(12) 0.0135(11) C15 0.0471(14) 0.0379(12) 0.0578(15) 0.0130(11) 0.0152(12) 0.0123(11) C16 0.0500(15) 0.0470(14) 0.0500(14) 0.0125(11) 0.0163(12) 0.0177(11) C21 0.0610(18) 0.0502(15) 0.0610(17) 0.0077(13) 0.0193(14) 0.0218(13) C45 0.0672(19) 0.0500(15) 0.0643(18) 0.0064(13) 0.0291(15) 0.0227(14) C9 0.0444(13) 0.0304(12) 0.0518(14) 0.0075(10) 0.0118(11) 0.0119(10) C27 0.0374(12) 0.0364(12) 0.0605(15) 0.0084(11) 0.0189(11) 0.0128(10) C35 0.0432(14) 0.0404(13) 0.0487(14) 0.0097(11) 0.0110(11) 0.0117(10) C24 0.0418(14) 0.0354(12) 0.0686(17) 0.0057(12) 0.0188(13) 0.0095(10) C8 0.0570(16) 0.0322(12) 0.0541(15) 0.0067(11) 0.0205(13) 0.0169(11) C31 0.0425(13) 0.0356(12) 0.0531(14) 0.0061(10) 0.0116(11) 0.0108(10) C20 0.0663(19) 0.0664(19) 0.0551(16) 0.0078(14) 0.0235(15) 0.0309(15) C38 0.0501(15) 0.0512(15) 0.0454(14) 0.0107(11) 0.0145(12) 0.0139(12) C3 0.0532(17) 0.0427(14) 0.089(2) 0.0146(14) 0.0357(16) 0.0082(12) C39 0.0666(19) 0.0556(17) 0.0531(16) -0.0024(13) 0.0253(15) 0.0052(14) C34 0.0508(15) 0.0351(12) 0.0565(15) 0.0104(11) 0.0155(12) 0.0139(11) C2 0.0660(18) 0.0334(12) 0.0612(16) 0.0099(11) 0.0306(14) 0.0147(12) C30 0.0476(14) 0.0373(13) 0.0600(16) 0.0050(11) 0.0191(13) 0.0126(11) C12 0.0481(14) 0.0313(12) 0.0614(16) 0.0108(11) 0.0159(12) 0.0128(10) C40 0.0658(19) 0.0509(16) 0.0554(16) 0.0006(13) 0.0225(15) 0.0043(14) C33 0.0453(14) 0.0372(12) 0.0527(14) 0.0079(11) 0.0150(11) 0.0142(10) C43 0.0667(18) 0.0462(15) 0.0568(16) 0.0078(12) 0.0194(14) 0.0186(13) C17 0.0637(18) 0.0502(15) 0.0531(15) 0.0088(12) 0.0263(14) 0.0144(13) C10 0.0483(14) 0.0339(12) 0.0558(15) 0.0104(11) 0.0182(12) 0.0132(10) C44 0.076(2) 0.100(3) 0.076(2) 0.023(2) 0.0392(19) 0.043(2) C42 0.0718(19) 0.0580(17) 0.0520(15) 0.0102(13) 0.0269(15) 0.0268(14) C41 0.0501(15) 0.0557(16) 0.0466(14) 0.0139(12) 0.0145(12) 0.0171(12) C22 0.201(7) 0.085(3) 0.176(6) 0.029(3) 0.148(6) 0.017(4) C11 0.0468(14) 0.0338(12) 0.0596(15) 0.0085(11) 0.0183(12) 0.0152(10) C19 0.0557(16) 0.0647(17) 0.0542(16) 0.0196(13) 0.0239(13) 0.0266(14) C32 0.0441(14) 0.0397(13) 0.0521(14) 0.0112(11) 0.0156(11) 0.0118(10) C18 0.0641(18) 0.0507(16) 0.0642(18) 0.0141(13) 0.0287(15) 0.0153(13) 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' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 4 8 0.0693 0 -4 -8 0.0693 0 9 -3 0.0545 6 -6 -2 0.0934 1 -2 9 0.0938 -1 2 -9 0.0938 -6 6 1 0.1259 0 8 4 0.0538 2 8 -4 0.0588 6 0 -2 0.0959 -6 0 2 0.1374 2 8 0 0.0492 -3 10 -1 0.0763 0 -9 1 0.0265 -1 1 10 0.0793 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 S1 C1 104.13(18) C24 S3 C23 104.88(17) C41 S4 C44 103.36(17) C22 S2 C19 103.76(19) C33 O3 C46 118.0(2) C11 O1 C45 117.5(2) C27 C26 C25 121.2(3) C37 N4 C38 120.2(2) C15 N2 C16 121.3(2) C30 N3 C27 119.0(2) C8 N1 C5 118.3(2) C5 C6 C7 121.0(3) C26 C25 C24 120.0(3) C29 C28 C27 120.4(3) C28 C29 C24 121.3(3) C2 C7 C6 120.1(3) O2 C14 C13 121.0(2) O2 C14 C9 119.6(2) C9 C14 C13 119.4(2) O4 C36 C35 120.8(2) O4 C36 C31 119.8(2) C31 C36 C35 119.4(2) C3 C4 C5 120.2(3) C6 C5 N1 123.0(2) C6 C5 C4 118.8(2) C4 C5 N1 118.1(2) C14 C13 C15 121.8(2) C12 C13 C14 119.0(2) C12 C13 C15 119.2(2) N4 C37 C35 123.1(3) N2 C15 C13 121.9(2) C21 C16 N2 117.8(3) C21 C16 C17 118.1(3) C17 C16 N2 124.0(3) C20 C21 C16 121.4(3) C14 C9 C8 119.4(2) C14 C9 C10 120.2(2) C10 C9 C8 120.4(2) C26 C27 N3 118.1(2) C26 C27 C28 118.4(2) C28 C27 N3 123.4(3) C36 C35 C37 122.0(3) C34 C35 C36 119.3(2) C34 C35 C37 118.6(2) C25 C24 S3 124.7(2) C29 C24 S3 116.6(2) C29 C24 C25 118.6(2) N1 C8 C9 122.5(2) C36 C31 C30 119.7(2) C36 C31 C32 119.8(2) C32 C31 C30 120.5(2) C21 C20 C19 120.2(3) C39 C38 N4 123.9(3) C43 C38 N4 118.4(3) C43 C38 C39 117.7(3) C4 C3 C2 121.0(3) C40 C39 C38 120.9(3) C33 C34 C35 121.4(2) C7 C2 S1 124.2(2) C7 C2 C3 118.9(2) C3 C2 S1 116.9(2) N3 C30 C31 121.9(3) C11 C12 C13 121.5(2) C39 C40 C41 121.1(3) O3 C33 C34 114.9(2) O3 C33 C32 125.7(2) C34 C33 C32 119.4(2) C38 C43 C42 121.7(3) C18 C17 C16 120.6(3) C11 C10 C9 120.5(3) C43 C42 C41 120.0(3) C40 C41 S4 116.2(2) C42 C41 S4 125.3(2) C42 C41 C40 118.5(3) O1 C11 C12 115.6(2) O1 C11 C10 125.0(3) C12 C11 C10 119.4(2) C20 C19 S2 116.2(2) C18 C19 S2 124.7(3) C18 C19 C20 119.0(3) C33 C32 C31 120.7(2) C17 C18 C19 120.7(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C1 1.766(5) S1 C2 1.762(3) S3 C23 1.774(4) S3 C24 1.767(3) S4 C44 1.787(4) S4 C41 1.763(3) S2 C22 1.748(5) S2 C19 1.758(3) O2 C14 1.351(3) O4 C36 1.349(3) O3 C46 1.414(3) O3 C33 1.370(3) O1 C45 1.416(4) O1 C11 1.371(3) C26 C25 1.388(4) C26 C27 1.386(4) N4 C37 1.276(4) N4 C38 1.419(4) N2 C15 1.280(4) N2 C16 1.409(4) N3 C27 1.420(3) N3 C30 1.265(4) N1 C5 1.414(3) N1 C8 1.258(4) C6 C7 1.387(4) C6 C5 1.379(4) C25 C24 1.389(4) C28 C29 1.379(4) C28 C27 1.390(4) C29 C24 1.384(4) C7 C2 1.385(4) C14 C13 1.416(3) C14 C9 1.390(4) C36 C35 1.414(4) C36 C31 1.395(4) C4 C5 1.393(4) C4 C3 1.376(4) C13 C15 1.444(4) C13 C12 1.389(4) C37 C35 1.450(4) C16 C21 1.392(4) C16 C17 1.392(4) C21 C20 1.371(4) C9 C8 1.467(3) C9 C10 1.395(4) C35 C34 1.383(4) C31 C30 1.471(3) C31 C32 1.397(4) C20 C19 1.387(5) C38 C39 1.399(4) C38 C43 1.380(4) C3 C2 1.388(4) C39 C40 1.362(4) C34 C33 1.382(4) C12 C11 1.383(4) C40 C41 1.390(4) C33 C32 1.384(4) C43 C42 1.382(4) C17 C18 1.379(4) C10 C11 1.384(3) C42 C41 1.386(4) C19 C18 1.385(4) 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 O2 H2 N2 0.82 1.88 2.610(3) 147.3 . O4 H4A N4 0.82 1.91 2.641(3) 147.9 . C23 H23A O3 0.96 2.56 3.483(4) 161.0 1_545 C1 H1B O1 0.96 2.36 3.319(4) 172.7 1_545 C20 H20 O4 0.93 2.63 3.457(4) 148.6 2_775 loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0.0079 4.0097 8.0071 0.0820 0.1195 0.9956 -0.0079 -4.0097 -8.0071 -0.0820 -0.1195 -0.9956 -0.0056 8.9789 -2.9997 0.9470 0.1611 0.1643 5.9961 -6.0025 -2.0104 -0.2105 -0.9672 0.0007 1.0100 -1.9796 9.0050 -0.4671 -0.1329 0.8715 -1.0100 1.9796 -9.0050 0.4671 0.1329 -0.8715 -5.9972 6.0004 1.0096 0.2468 0.9621 -0.0995 0.0025 7.9949 4.0053 0.5997 0.1774 0.8050 1.9925 7.9757 -4.0032 0.9821 -0.1434 0.1827 5.9946 -0.0124 -2.0087 0.3482 -0.8495 0.3079 -5.9946 0.0124 2.0087 -0.3482 0.8495 -0.3079 1.9970 7.9839 -0.0001 0.8368 -0.1229 0.5781 -3.0020 9.9855 -0.9944 0.8297 0.6106 0.1604 0.0034 -8.9830 0.9982 -0.8744 -0.1714 -0.3620 -0.9885 1.0202 10.0090 -0.3160 0.2108 0.9554