#------------------------------------------------------------------------------ #$Date: 2019-12-26 20:38:43 +0200 (Thu, 26 Dec 2019) $ #$Revision: 246065 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/31/16/2311631.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2311631 loop_ _publ_author_name 'Aitipamula, Srinivasulu' 'Chow, Pui Shan' 'Tan, Reginald B. H.' _publ_section_title ; Solvates of the antifungal drug griseofulvin: structural, thermochemical and conformational analysis. ; _journal_issue 'Pt 1' _journal_name_full 'Acta crystallographica Section B, Structural science, crystal engineering and materials' _journal_page_first 54 _journal_page_last 62 _journal_paper_doi 10.1107/S2052520613026711 _journal_volume 70 _journal_year 2014 _chemical_formula_sum 'C36 H39 Cl2 N O14' _chemical_formula_weight 780.58 _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.6852(17) _cell_length_b 15.047(3) _cell_length_c 27.605(6) _cell_measurement_reflns_used 9491 _cell_measurement_temperature 163(2) _cell_measurement_theta_max 31.0271 _cell_measurement_theta_min 2.0022 _cell_volume 3607.6(13) _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 163(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Rigaku Saturn 70 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0523 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 15583 _diffrn_reflns_theta_full 28.26 _diffrn_reflns_theta_max 28.26 _diffrn_reflns_theta_min 1.48 _exptl_absorpt_coefficient_mu 0.252 _exptl_absorpt_correction_T_max 0.9467 _exptl_absorpt_correction_T_min 0.9216 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'R. H. Blessing, Acta Cryst. 1995 A51, 33-38' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.437 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1632 _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.22 _refine_diff_density_max 0.205 _refine_diff_density_min -0.345 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 487 _refine_ls_number_reflns 8492 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.089 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0510 _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^)+(0.0430P)^2^+0.9983P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1078 _refine_ls_wR_factor_ref 0.1167 _reflns_number_gt 7628 _reflns_number_total 8492 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL shelxs in P2(1)2(1)2(1) CELL 0.71073 8.6852 15.0475 27.6051 90.000 90.000 90.000 ZERR 4.00 0.0017 0.0030 0.0055 0.000 0.000 0.000 LATT -1 SYMM 0.5-X, -Y, 0.5+Z SYMM -X, 0.5+Y, 0.5-Z SYMM 0.5+X, 0.5-Y, -Z SFAC C H N O Cl UNIT 144 156 4 56 8 L.S. 4 ACTA BOND $H FMAP 2 PLAN 5 SIZE 0.33 0.33 0.22 WGHT 0.043100 0.996200 FVAR 0.316010 TEMP -110 MOLE 1 Cl2A 5 0.254663 0.933438 0.796166 11.000000 0.021820 0.032910 = 0.035230 -0.003900 -0.000660 0.001490 O6A 4 0.917890 0.957503 0.841928 11.000000 0.020510 0.038450 = 0.030380 -0.007640 -0.002830 -0.001790 O4A 4 0.934074 0.859506 0.743776 11.000000 0.022220 0.042370 = 0.034090 -0.005820 0.000550 -0.000270 O2A 4 0.625847 0.958235 0.675983 11.000000 0.036280 0.028090 = 0.026880 0.003320 -0.001920 0.002120 O3A 4 0.524242 0.851345 0.742977 11.000000 0.023020 0.029610 = 0.023580 -0.005300 0.000660 -0.000250 O5A 4 0.386102 1.026541 0.877871 11.000000 0.026890 0.036350 = 0.029870 -0.007210 0.001620 0.004400 C10A 1 0.655362 0.993344 0.863342 11.000000 0.026170 0.029810 = 0.026420 -0.003010 -0.000120 0.002230 AFIX 43 H10A 2 0.686623 1.025412 0.891307 11.000000 -1.200000 AFIX 0 C12A 1 0.447101 0.939055 0.811332 11.000000 0.022560 0.029800 = 0.028410 -0.001060 0.000410 0.002560 C8A 1 0.716019 0.905026 0.793354 11.000000 0.025960 0.023950 = 0.024240 -0.001590 -0.001130 -0.001130 C13A 1 0.558062 0.898653 0.783218 11.000000 0.024090 0.024020 = 0.022930 -0.001380 -0.000840 -0.000010 C11A 1 0.498316 0.986955 0.851477 11.000000 0.024880 0.027910 = 0.027310 -0.000630 0.002840 0.004030 C9A 1 0.764051 0.952886 0.834240 11.000000 0.021330 0.026670 = 0.027940 0.000210 -0.001090 -0.000880 O1A 4 0.848397 0.712951 0.594646 11.000000 0.039750 0.049990 = 0.038830 -0.016030 0.012990 -0.006800 C14A 1 0.683466 0.677658 0.762725 11.000000 0.042970 0.035630 = 0.034650 -0.000030 -0.001100 0.003870 AFIX 137 H14E 2 0.783728 0.690549 0.777417 11.000000 -1.500000 H14D 2 0.673341 0.613450 0.757710 11.000000 -1.500000 H14F 2 0.601259 0.698332 0.784274 11.000000 -1.500000 AFIX 0 C2A 1 0.734206 0.836767 0.631253 11.000000 0.031610 0.038160 = 0.024250 -0.001320 0.002390 -0.006620 AFIX 43 H2A 2 0.734781 0.869509 0.601829 11.000000 -1.200000 AFIX 0 C3A 1 0.676494 0.874399 0.671482 11.000000 0.025810 0.029420 = 0.026720 -0.002170 -0.003580 -0.001320 C1A 1 0.795996 0.746638 0.631861 11.000000 0.022230 0.039380 = 0.033580 -0.010240 0.004890 -0.006700 C7A 1 0.796830 0.864356 0.753315 11.000000 0.025170 0.025490 = 0.025800 -0.001960 -0.000530 0.001150 C17A 1 0.970660 1.012164 0.881502 11.000000 0.026830 0.044760 = 0.029850 -0.008670 -0.002510 -0.006760 AFIX 137 H17D 2 0.935778 1.073440 0.876580 11.000000 -1.500000 H17F 2 1.083397 1.010821 0.882795 11.000000 -1.500000 H17E 2 0.928663 0.989376 0.912020 11.000000 -1.500000 AFIX 0 C5A 1 0.671090 0.725486 0.713989 11.000000 0.028040 0.026990 = 0.029150 -0.002160 0.002440 0.001710 AFIX 13 H5A 2 0.571563 0.707291 0.698713 11.000000 -1.200000 AFIX 0 C4A 1 0.668544 0.826772 0.719644 11.000000 0.020990 0.028130 = 0.024210 -0.002970 0.001080 0.002450 C16A 1 0.431175 1.083658 0.917344 11.000000 0.037400 0.035880 = 0.027130 -0.007440 -0.000160 0.004440 AFIX 137 H16E 2 0.493423 1.049831 0.940512 11.000000 -1.500000 H16D 2 0.339003 1.106460 0.933619 11.000000 -1.500000 H16F 2 0.491730 1.133501 0.904730 11.000000 -1.500000 AFIX 0 C15A 1 0.637272 1.014297 0.633693 11.000000 0.043320 0.036820 = 0.036050 0.009530 -0.005640 -0.009050 AFIX 137 H15E 2 0.745830 1.021803 0.624919 11.000000 -1.500000 H15F 2 0.591876 1.072491 0.640767 11.000000 -1.500000 H15D 2 0.581864 0.986650 0.606688 11.000000 -1.500000 AFIX 0 C6A 1 0.801136 0.698539 0.679504 11.000000 0.028150 0.037380 = 0.033720 -0.006590 0.001410 0.003030 AFIX 23 H6AA 2 0.901232 0.710629 0.695345 11.000000 -1.200000 H6AB 2 0.794750 0.633801 0.673436 11.000000 -1.200000 AFIX 0 MOLE 2 Cl1 5 1.308924 0.552208 0.987575 11.000000 0.022150 0.050590 = 0.034600 -0.009340 -0.000290 -0.001690 O4 4 0.622840 0.463647 0.952489 11.000000 0.022030 0.037470 = 0.037390 -0.006280 -0.002260 -0.000680 O5 4 1.187297 0.685315 1.052211 11.000000 0.028660 0.039850 = 0.036280 -0.013220 0.000250 -0.008630 C7 1 0.760596 0.478426 0.955032 11.000000 0.023260 0.027500 = 0.027860 0.001840 -0.002700 0.001400 O3 4 1.030886 0.461045 0.942549 11.000000 0.021590 0.032530 = 0.028380 -0.008100 -0.001130 -0.001940 O6 4 0.649316 0.621051 1.021959 11.000000 0.026090 0.036040 = 0.037470 -0.011630 0.002670 0.002780 O2 4 0.942639 0.315295 0.987103 11.000000 0.039780 0.032550 = 0.025870 -0.000310 -0.006230 0.002040 C2 1 0.804322 0.264005 0.917597 11.000000 0.027080 0.032200 = 0.029460 -0.002770 -0.000520 -0.001320 AFIX 43 H2 2 0.797673 0.205591 0.930484 11.000000 -1.200000 AFIX 0 C10 1 0.914844 0.657941 1.039772 11.000000 0.026850 0.030770 = 0.027890 -0.005040 0.000260 0.000670 AFIX 43 H10 2 0.886581 0.702148 1.062675 11.000000 -1.200000 AFIX 0 O1 4 0.674430 0.222854 0.847240 11.000000 0.056210 0.040420 = 0.044070 -0.007140 -0.014310 -0.012560 C12 1 1.116552 0.575920 0.997046 11.000000 0.023210 0.034730 = 0.027820 -0.003150 0.000200 -0.003020 C9 1 0.801945 0.610006 1.015719 11.000000 0.027500 0.025880 = 0.028460 -0.000500 -0.000330 0.001170 C13 1 1.001992 0.528840 0.973962 11.000000 0.024290 0.026100 = 0.024400 -0.004030 -0.000610 0.000010 C8 1 0.845583 0.543677 0.982297 11.000000 0.023110 0.031470 = 0.026470 -0.001200 -0.003550 0.001060 C11 1 1.070714 0.641137 1.030278 11.000000 0.027270 0.031640 = 0.029670 -0.002670 -0.002020 -0.007250 C1 1 0.736881 0.281919 0.870932 11.000000 0.031790 0.033350 = 0.031180 -0.006010 0.001280 -0.001860 C6 1 0.739823 0.376188 0.852147 11.000000 0.030580 0.033160 = 0.029490 -0.003780 -0.007370 0.001950 AFIX 23 H6A 2 0.641762 0.405689 0.860847 11.000000 -1.200000 H6B 2 0.746760 0.374762 0.816359 11.000000 -1.200000 AFIX 0 C17 1 0.600505 0.683179 1.058765 11.000000 0.030900 0.037370 = 0.039220 -0.014000 0.004460 0.005550 AFIX 137 H17A 2 0.640605 0.664312 1.090314 11.000000 -1.500000 H17B 2 0.487769 0.684878 1.059935 11.000000 -1.500000 H17C 2 0.640021 0.742504 1.051019 11.000000 -1.500000 AFIX 0 C3 1 0.876685 0.327475 0.943639 11.000000 0.024720 0.030030 = 0.024220 0.000340 -0.000730 0.003190 C5 1 0.873344 0.431238 0.871970 11.000000 0.026740 0.031430 = 0.025540 0.000270 -0.001180 0.000590 AFIX 13 H6 2 0.970469 0.405949 0.858242 11.000000 -1.200000 AFIX 0 C4 1 0.883431 0.423008 0.927432 11.000000 0.022460 0.028420 = 0.026230 -0.004760 -0.003340 -0.002590 C14 1 0.862588 0.527223 0.855242 11.000000 0.048260 0.037820 = 0.033280 0.005010 0.001870 -0.002300 AFIX 137 H14A 2 0.869349 0.529538 0.819828 11.000000 -1.500000 H14B 2 0.947356 0.561510 0.869373 11.000000 -1.500000 H14C 2 0.764118 0.552536 0.865736 11.000000 -1.500000 AFIX 0 C15 1 0.940173 0.225817 1.006729 11.000000 0.051980 0.036850 = 0.032320 0.005590 -0.003890 0.007350 AFIX 137 H15A 2 0.833250 0.206715 1.011225 11.000000 -1.500000 H15B 2 0.993584 0.225004 1.037997 11.000000 -1.500000 H15C 2 0.992018 0.185318 0.984215 11.000000 -1.500000 AFIX 0 C16 1 1.149442 0.750122 1.088903 11.000000 0.042850 0.047630 = 0.046830 -0.024270 0.000260 -0.009770 AFIX 137 H16A 2 1.089391 0.798346 1.074332 11.000000 -1.500000 H16B 2 1.244466 0.774328 1.102774 11.000000 -1.500000 H16C 2 1.088779 0.721674 1.114507 11.000000 -1.500000 AFIX 0 MOLE 3 N1 3 0.201365 0.718806 0.820483 11.000000 0.052300 0.030270 = 0.037300 -0.002330 0.000420 -0.008800 O8 4 0.321475 0.730248 0.843141 11.000000 0.068990 0.046920 = 0.047210 -0.005740 -0.021670 0.006100 C18 1 0.208941 0.712922 0.766543 11.000000 0.038070 0.029210 = 0.032450 0.001590 -0.000060 -0.000320 AFIX 23 H18A 2 0.309664 0.735315 0.755014 11.000000 -1.200000 H18B 2 0.126928 0.750012 0.751997 11.000000 -1.200000 AFIX 0 O7 4 0.076029 0.710930 0.839798 11.000000 0.074980 0.067860 = 0.057290 -0.016080 0.025240 -0.032440 C19 1 0.188606 0.618279 0.751470 11.000000 0.095950 0.028730 = 0.042090 -0.003010 -0.003130 -0.001710 AFIX 137 H19A 2 0.269750 0.581850 0.766106 11.000000 -1.500000 H19B 2 0.194985 0.614002 0.716103 11.000000 -1.500000 H19C 2 0.087745 0.596909 0.762316 11.000000 -1.500000 AFIX 0 Q1 1 0.089400 0.167500 0.076100 11.000000 0.050000 0.21 Q2 1 0.435700 0.542200 0.760100 11.000000 0.050000 0.20 Q3 1 0.437600 0.783100 0.058700 11.000000 0.050000 0.20 Q4 1 0.440600 0.980400 0.714900 11.000000 0.050000 0.20 Q5 1 0.360600 0.778900 0.027200 11.000000 0.050000 0.19 HKLF 4 END ; _cod_data_source_file zb5031sup1.cif _cod_data_source_block GF-NE2-1 _cod_original_sg_symbol_H-M 'P21 21 21' _cod_database_code 2311631 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_symmetry_multiplicity Cl Cl2A 0.25466(7) 0.93344(5) 0.79617(2) 0.02999(14) Uani d . 1 1 O O6A 0.91789(19) 0.95750(13) 0.84193(7) 0.0298(4) Uani d . 1 1 O O4A 0.9341(2) 0.85951(14) 0.74378(7) 0.0329(4) Uani d . 1 1 O O2A 0.6258(2) 0.95824(13) 0.67598(7) 0.0304(4) Uani d . 1 1 O O3A 0.52424(19) 0.85135(12) 0.74298(6) 0.0254(4) Uani d . 1 1 O O5A 0.3861(2) 1.02654(13) 0.87787(7) 0.0310(4) Uani d . 1 1 C C10A 0.6554(3) 0.99334(18) 0.86334(10) 0.0275(5) Uani d . 1 1 H H10A 0.6866 1.0254 0.8913 0.033 Uiso calc R 1 1 C C12A 0.4471(3) 0.93905(19) 0.81133(9) 0.0269(5) Uani d . 1 1 C C8A 0.7160(3) 0.90503(17) 0.79335(9) 0.0247(5) Uani d . 1 1 C C13A 0.5581(3) 0.89865(17) 0.78322(9) 0.0237(5) Uani d . 1 1 C C11A 0.4983(3) 0.98695(18) 0.85148(10) 0.0267(5) Uani d . 1 1 C C9A 0.7641(3) 0.95289(17) 0.83424(9) 0.0253(5) Uani d . 1 1 O O1A 0.8484(2) 0.71295(15) 0.59465(8) 0.0429(5) Uani d . 1 1 C C14A 0.6835(4) 0.6777(2) 0.76273(11) 0.0377(7) Uani d . 1 1 H H14E 0.7837 0.6905 0.7774 0.057 Uiso calc R 1 1 H H14D 0.6733 0.6134 0.7577 0.057 Uiso calc R 1 1 H H14F 0.6013 0.6983 0.7843 0.057 Uiso calc R 1 1 C C2A 0.7342(3) 0.8368(2) 0.63125(10) 0.0313(6) Uani d . 1 1 H H2A 0.7348 0.8695 0.6018 0.038 Uiso calc R 1 1 C C3A 0.6765(3) 0.87440(19) 0.67148(10) 0.0273(5) Uani d . 1 1 C C1A 0.7960(3) 0.7466(2) 0.63186(11) 0.0317(6) Uani d . 1 1 C C7A 0.7968(3) 0.86436(18) 0.75331(9) 0.0255(5) Uani d . 1 1 C C17A 0.9707(3) 1.0122(2) 0.88150(10) 0.0338(6) Uani d . 1 1 H H17D 0.9358 1.0734 0.8766 0.051 Uiso calc R 1 1 H H17F 1.0834 1.0108 0.8828 0.051 Uiso calc R 1 1 H H17E 0.9287 0.9894 0.9120 0.051 Uiso calc R 1 1 C C5A 0.6711(3) 0.72549(18) 0.71399(10) 0.0281(5) Uani d . 1 1 H H5A 0.5716 0.7073 0.6987 0.034 Uiso calc R 1 1 C C4A 0.6685(3) 0.82677(18) 0.71964(9) 0.0244(5) Uani d . 1 1 C C16A 0.4312(3) 1.0837(2) 0.91734(10) 0.0335(6) Uani d . 1 1 H H16E 0.4934 1.0498 0.9405 0.050 Uiso calc R 1 1 H H16D 0.3390 1.1065 0.9336 0.050 Uiso calc R 1 1 H H16F 0.4917 1.1335 0.9047 0.050 Uiso calc R 1 1 C C15A 0.6373(4) 1.0143(2) 0.63369(11) 0.0387(7) Uani d . 1 1 H H15E 0.7458 1.0218 0.6249 0.058 Uiso calc R 1 1 H H15F 0.5919 1.0725 0.6408 0.058 Uiso calc R 1 1 H H15D 0.5819 0.9867 0.6067 0.058 Uiso calc R 1 1 C C6A 0.8011(3) 0.6985(2) 0.67950(10) 0.0331(6) Uani d . 1 1 H H6AA 0.9012 0.7106 0.6953 0.040 Uiso calc R 1 1 H H6AB 0.7947 0.6338 0.6734 0.040 Uiso calc R 1 1 Cl Cl1 1.30892(7) 0.55221(5) 0.98757(3) 0.03578(17) Uani d . 1 1 O O4 0.6228(2) 0.46365(13) 0.95249(7) 0.0323(4) Uani d . 1 1 O O5 1.1873(2) 0.68532(14) 1.05221(7) 0.0349(5) Uani d . 1 1 C C7 0.7606(3) 0.47843(17) 0.95503(9) 0.0262(5) Uani d . 1 1 O O3 1.03089(19) 0.46104(13) 0.94255(7) 0.0275(4) Uani d . 1 1 O O6 0.6493(2) 0.62105(14) 1.02196(8) 0.0332(4) Uani d . 1 1 O O2 0.9426(2) 0.31530(14) 0.98710(7) 0.0327(4) Uani d . 1 1 C C2 0.8043(3) 0.26401(19) 0.91760(10) 0.0296(6) Uani d . 1 1 H H2 0.7977 0.2056 0.9305 0.035 Uiso calc R 1 1 C C10 0.9148(3) 0.65794(19) 1.03977(10) 0.0285(5) Uani d . 1 1 H H10 0.8866 0.7021 1.0627 0.034 Uiso calc R 1 1 O O1 0.6744(3) 0.22285(15) 0.84724(9) 0.0469(6) Uani d . 1 1 C C12 1.1166(3) 0.57592(19) 0.99705(10) 0.0286(6) Uani d . 1 1 C C9 0.8019(3) 0.61001(18) 1.01572(10) 0.0273(5) Uani d . 1 1 C C13 1.0020(3) 0.52884(18) 0.97396(9) 0.0249(5) Uani d . 1 1 C C8 0.8456(3) 0.54368(18) 0.98230(10) 0.0270(5) Uani d . 1 1 C C11 1.0707(3) 0.64114(19) 1.03028(10) 0.0295(6) Uani d . 1 1 C C1 0.7369(3) 0.28192(19) 0.87093(10) 0.0321(6) Uani d . 1 1 C C6 0.7398(3) 0.37619(19) 0.85215(10) 0.0311(6) Uani d . 1 1 H H6A 0.6418 0.4057 0.8608 0.037 Uiso calc R 1 1 H H6B 0.7468 0.3748 0.8164 0.037 Uiso calc R 1 1 C C17 0.6005(3) 0.6832(2) 1.05876(11) 0.0358(7) Uani d . 1 1 H H17A 0.6406 0.6643 1.0903 0.054 Uiso calc R 1 1 H H17B 0.4878 0.6849 1.0599 0.054 Uiso calc R 1 1 H H17C 0.6400 0.7425 1.0510 0.054 Uiso calc R 1 1 C C3 0.8767(3) 0.32747(18) 0.94364(10) 0.0263(5) Uani d . 1 1 C C5 0.8733(3) 0.43124(19) 0.87197(10) 0.0279(5) Uani d . 1 1 H H6 0.9705 0.4059 0.8582 0.033 Uiso calc R 1 1 C C4 0.8834(3) 0.42301(18) 0.92743(9) 0.0257(5) Uani d . 1 1 C C14 0.8626(4) 0.5272(2) 0.85524(11) 0.0398(7) Uani d . 1 1 H H14A 0.8693 0.5295 0.8198 0.060 Uiso calc R 1 1 H H14B 0.9474 0.5615 0.8694 0.060 Uiso calc R 1 1 H H14C 0.7641 0.5525 0.8657 0.060 Uiso calc R 1 1 C C15 0.9402(4) 0.2258(2) 1.00673(11) 0.0404(7) Uani d . 1 1 H H15A 0.8333 0.2067 1.0112 0.061 Uiso calc R 1 1 H H15B 0.9936 0.2250 1.0380 0.061 Uiso calc R 1 1 H H15C 0.9920 0.1853 0.9842 0.061 Uiso calc R 1 1 C C16 1.1494(4) 0.7501(2) 1.08890(13) 0.0458(8) Uani d . 1 1 H H16A 1.0894 0.7983 1.0743 0.069 Uiso calc R 1 1 H H16B 1.2445 0.7743 1.1028 0.069 Uiso calc R 1 1 H H16C 1.0888 0.7217 1.1145 0.069 Uiso calc R 1 1 N N1 0.2014(3) 0.71881(17) 0.82048(10) 0.0400(6) Uani d . 1 1 O O8 0.3215(3) 0.73025(17) 0.84314(9) 0.0544(7) Uani d . 1 1 C C18 0.2089(3) 0.71292(19) 0.76654(10) 0.0332(6) Uani d . 1 1 H H18A 0.3097 0.7353 0.7550 0.040 Uiso calc R 1 1 H H18B 0.1269 0.7500 0.7520 0.040 Uiso calc R 1 1 O O7 0.0760(3) 0.71093(19) 0.83980(10) 0.0667(8) Uani d . 1 1 C C19 0.1886(5) 0.6183(2) 0.75147(13) 0.0556(10) Uani d . 1 1 H H19A 0.2697 0.5818 0.7661 0.083 Uiso calc R 1 1 H H19B 0.1950 0.6140 0.7161 0.083 Uiso calc R 1 1 H H19C 0.0877 0.5969 0.7623 0.083 Uiso calc R 1 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl2A 0.0218(3) 0.0329(3) 0.0352(3) 0.0015(3) -0.0007(3) -0.0039(3) O6A 0.0205(8) 0.0384(11) 0.0304(10) -0.0018(8) -0.0028(7) -0.0076(9) O4A 0.0222(9) 0.0424(12) 0.0341(10) -0.0003(8) 0.0005(8) -0.0058(9) O2A 0.0363(10) 0.0281(10) 0.0269(9) 0.0021(8) -0.0019(8) 0.0033(8) O3A 0.0230(8) 0.0296(10) 0.0236(9) -0.0002(7) 0.0007(7) -0.0053(8) O5A 0.0269(9) 0.0363(11) 0.0299(10) 0.0044(8) 0.0016(8) -0.0072(8) C10A 0.0262(12) 0.0298(13) 0.0264(12) 0.0022(10) -0.0001(10) -0.0030(11) C12A 0.0226(11) 0.0298(14) 0.0284(12) 0.0026(11) 0.0004(10) -0.0011(11) C8A 0.0260(12) 0.0240(12) 0.0242(11) -0.0011(10) -0.0011(10) -0.0016(10) C13A 0.0241(12) 0.0240(12) 0.0229(12) 0.0000(10) -0.0008(10) -0.0014(10) C11A 0.0249(12) 0.0279(13) 0.0273(13) 0.0040(10) 0.0028(10) -0.0006(11) C9A 0.0213(11) 0.0267(12) 0.0279(12) -0.0009(10) -0.0011(10) 0.0002(10) O1A 0.0397(11) 0.0500(14) 0.0388(12) -0.0068(10) 0.0130(10) -0.0160(11) C14A 0.0430(16) 0.0356(16) 0.0346(15) 0.0039(14) -0.0011(14) 0.0000(13) C2A 0.0316(14) 0.0382(15) 0.0242(12) -0.0066(12) 0.0024(11) -0.0013(11) C3A 0.0258(12) 0.0294(14) 0.0267(12) -0.0013(11) -0.0036(11) -0.0022(11) C1A 0.0222(12) 0.0394(15) 0.0336(14) -0.0067(11) 0.0049(11) -0.0102(12) C7A 0.0252(12) 0.0255(12) 0.0258(12) 0.0011(10) -0.0005(10) -0.0020(10) C17A 0.0268(13) 0.0448(17) 0.0299(14) -0.0068(12) -0.0025(11) -0.0087(13) C5A 0.0280(13) 0.0270(13) 0.0292(13) 0.0017(11) 0.0024(11) -0.0022(11) C4A 0.0210(11) 0.0281(13) 0.0242(12) 0.0024(10) 0.0011(10) -0.0030(10) C16A 0.0374(15) 0.0359(15) 0.0271(13) 0.0044(13) -0.0002(12) -0.0074(12) C15A 0.0433(16) 0.0368(16) 0.0360(16) -0.0091(13) -0.0056(13) 0.0095(13) C6A 0.0281(13) 0.0374(15) 0.0337(14) 0.0030(12) 0.0014(12) -0.0066(13) Cl1 0.0221(3) 0.0506(4) 0.0346(3) -0.0017(3) -0.0003(3) -0.0093(3) O4 0.0220(9) 0.0375(11) 0.0374(11) -0.0007(8) -0.0023(8) -0.0063(9) O5 0.0287(9) 0.0398(11) 0.0363(11) -0.0086(9) 0.0003(9) -0.0132(9) C7 0.0233(11) 0.0275(12) 0.0279(12) 0.0014(10) -0.0027(10) 0.0018(10) O3 0.0216(8) 0.0325(10) 0.0284(9) -0.0019(7) -0.0011(7) -0.0081(8) O6 0.0261(9) 0.0360(11) 0.0375(11) 0.0028(8) 0.0027(8) -0.0116(9) O2 0.0398(11) 0.0325(11) 0.0259(9) 0.0020(9) -0.0062(9) -0.0003(9) C2 0.0271(12) 0.0322(14) 0.0295(13) -0.0013(11) -0.0005(11) -0.0028(11) C10 0.0268(12) 0.0308(14) 0.0279(13) 0.0007(11) 0.0003(11) -0.0050(11) O1 0.0562(14) 0.0404(12) 0.0441(13) -0.0126(11) -0.0143(11) -0.0071(11) C12 0.0232(12) 0.0347(14) 0.0278(13) -0.0030(11) 0.0002(10) -0.0032(11) C9 0.0275(12) 0.0259(13) 0.0285(12) 0.0012(10) -0.0003(11) -0.0005(11) C13 0.0243(12) 0.0261(13) 0.0244(12) 0.0000(10) -0.0006(10) -0.0040(10) C8 0.0231(12) 0.0315(14) 0.0265(12) 0.0011(10) -0.0036(10) -0.0012(11) C11 0.0273(13) 0.0316(14) 0.0297(13) -0.0073(11) -0.0020(11) -0.0027(12) C1 0.0318(14) 0.0334(14) 0.0312(14) -0.0019(12) 0.0013(12) -0.0060(12) C6 0.0306(13) 0.0332(14) 0.0295(13) 0.0019(12) -0.0074(12) -0.0038(11) C17 0.0309(14) 0.0374(16) 0.0392(16) 0.0056(12) 0.0045(13) -0.0140(14) C3 0.0247(12) 0.0300(13) 0.0242(12) 0.0032(10) -0.0007(10) 0.0003(11) C5 0.0267(12) 0.0314(13) 0.0255(12) 0.0006(11) -0.0012(10) 0.0003(11) C4 0.0225(11) 0.0284(13) 0.0262(12) -0.0026(10) -0.0033(10) -0.0048(11) C14 0.0483(17) 0.0378(16) 0.0333(15) -0.0023(14) 0.0019(13) 0.0050(13) C15 0.0520(18) 0.0369(17) 0.0323(15) 0.0073(14) -0.0039(14) 0.0056(13) C16 0.0429(17) 0.0476(19) 0.0468(19) -0.0098(15) 0.0003(15) -0.0243(16) N1 0.0523(16) 0.0303(13) 0.0373(14) -0.0088(12) 0.0004(13) -0.0023(11) O8 0.0690(16) 0.0469(14) 0.0472(14) 0.0061(13) -0.0217(13) -0.0057(12) C18 0.0381(15) 0.0292(14) 0.0325(14) -0.0003(12) -0.0001(12) 0.0016(12) O7 0.0750(18) 0.0679(19) 0.0573(17) -0.0324(15) 0.0252(15) -0.0161(15) C19 0.096(3) 0.0287(16) 0.0421(18) -0.0017(18) -0.003(2) -0.0030(14) 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' Cl Cl 0.1484 0.1585 '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 C9A O6A C17A 117.5(2) C3A O2A C15A 116.9(2) C13A O3A C4A 108.06(19) C11A O5A C16A 118.2(2) C9A C10A C11A 119.8(3) C9A C10A H10A 120.1 C11A C10A H10A 120.1 C13A C12A C11A 116.9(2) C13A C12A Cl2A 121.3(2) C11A C12A Cl2A 121.8(2) C9A C8A C13A 119.1(2) C9A C8A C7A 133.5(2) C13A C8A C7A 107.1(2) O3A C13A C12A 122.9(2) O3A C13A C8A 114.3(2) C12A C13A C8A 122.7(2) O5A C11A C12A 115.2(2) O5A C11A C10A 122.9(2) C12A C11A C10A 122.0(2) O6A C9A C10A 124.1(2) O6A C9A C8A 116.5(2) C10A C9A C8A 119.4(2) C5A C14A H14E 109.5 C5A C14A H14D 109.5 H14E C14A H14D 109.5 C5A C14A H14F 109.5 H14E C14A H14F 109.5 H14D C14A H14F 109.5 C3A C2A C1A 121.3(3) C3A C2A H2A 119.3 C1A C2A H2A 119.3 O2A C3A C2A 126.5(3) O2A C3A C4A 110.4(2) C2A C3A C4A 123.0(3) O1A C1A C2A 120.6(3) O1A C1A C6A 121.4(3) C2A C1A C6A 118.0(2) O4A C7A C8A 131.6(3) O4A C7A C4A 123.2(2) C8A C7A C4A 105.2(2) O6A C17A H17D 109.5 O6A C17A H17F 109.5 H17D C17A H17F 109.5 O6A C17A H17E 109.5 H17D C17A H17E 109.5 H17F C17A H17E 109.5 C14A C5A C6A 111.7(2) C14A C5A C4A 112.3(2) C6A C5A C4A 109.7(2) C14A C5A H5A 107.6 C6A C5A H5A 107.6 C4A C5A H5A 107.6 O3A C4A C3A 107.9(2) O3A C4A C5A 108.1(2) C3A C4A C5A 112.4(2) O3A C4A C7A 105.0(2) C3A C4A C7A 108.7(2) C5A C4A C7A 114.3(2) O5A C16A H16E 109.5 O5A C16A H16D 109.5 H16E C16A H16D 109.5 O5A C16A H16F 109.5 H16E C16A H16F 109.5 H16D C16A H16F 109.5 O2A C15A H15E 109.5 O2A C15A H15F 109.5 H15E C15A H15F 109.5 O2A C15A H15D 109.5 H15E C15A H15D 109.5 H15F C15A H15D 109.5 C1A C6A C5A 113.2(2) C1A C6A H6AA 108.9 C5A C6A H6AA 108.9 C1A C6A H6AB 108.9 C5A C6A H6AB 108.9 H6AA C6A H6AB 107.7 C11 O5 C16 118.4(2) O4 C7 C8 131.1(3) O4 C7 C4 123.2(2) C8 C7 C4 105.7(2) C13 O3 C4 108.25(19) C9 O6 C17 117.3(2) C3 O2 C15 117.0(2) C3 C2 C1 122.2(3) C3 C2 H2 118.9 C1 C2 H2 118.9 C9 C10 C11 120.0(3) C9 C10 H10 120.0 C11 C10 H10 120.0 C13 C12 C11 117.2(2) C13 C12 Cl1 121.5(2) C11 C12 Cl1 121.2(2) O6 C9 C10 124.8(2) O6 C9 C8 115.8(2) C10 C9 C8 119.4(2) O3 C13 C12 123.1(2) O3 C13 C8 113.8(2) C12 C13 C8 123.0(2) C13 C8 C9 118.8(2) C13 C8 C7 107.7(2) C9 C8 C7 133.3(2) O5 C11 C12 115.1(2) O5 C11 C10 123.4(3) C12 C11 C10 121.5(2) O1 C1 C2 121.3(3) O1 C1 C6 120.2(3) C2 C1 C6 118.4(2) C1 C6 C5 113.5(2) C1 C6 H6A 108.9 C5 C6 H6A 108.9 C1 C6 H6B 108.9 C5 C6 H6B 108.9 H6A C6 H6B 107.7 O6 C17 H17A 109.5 O6 C17 H17B 109.5 H17A C17 H17B 109.5 O6 C17 H17C 109.5 H17A C17 H17C 109.5 H17B C17 H17C 109.5 O2 C3 C2 125.3(3) O2 C3 C4 112.3(2) C2 C3 C4 122.3(2) C14 C5 C6 111.1(2) C14 C5 C4 112.5(2) C6 C5 C4 110.9(2) C14 C5 H6 107.4 C6 C5 H6 107.4 C4 C5 H6 107.4 O3 C4 C3 108.8(2) O3 C4 C5 107.6(2) C3 C4 C5 111.7(2) O3 C4 C7 104.5(2) C3 C4 C7 109.9(2) C5 C4 C7 113.9(2) C5 C14 H14A 109.5 C5 C14 H14B 109.5 H14A C14 H14B 109.5 C5 C14 H14C 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 O2 C15 H15A 109.5 O2 C15 H15B 109.5 H15A C15 H15B 109.5 O2 C15 H15C 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 O5 C16 H16A 109.5 O5 C16 H16B 109.5 H16A C16 H16B 109.5 O5 C16 H16C 109.5 H16A C16 H16C 109.5 H16B C16 H16C 109.5 O7 N1 O8 123.3(3) O7 N1 C18 118.0(3) O8 N1 C18 118.6(3) N1 C18 C19 109.2(3) N1 C18 H18A 109.8 C19 C18 H18A 109.8 N1 C18 H18B 109.8 C19 C18 H18B 109.8 H18A C18 H18B 108.3 C18 C19 H19A 109.5 C18 C19 H19B 109.5 H19A C19 H19B 109.5 C18 C19 H19C 109.5 H19A C19 H19C 109.5 H19B C19 H19C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl2A C12A 1.725(3) O6A C9A 1.355(3) O6A C17A 1.442(3) O4A C7A 1.223(3) O2A C3A 1.342(3) O2A C15A 1.444(3) O3A C13A 1.352(3) O3A C4A 1.457(3) O5A C11A 1.355(3) O5A C16A 1.442(3) C10A C9A 1.381(4) C10A C11A 1.406(3) C10A H10A 0.9500 C12A C13A 1.379(4) C12A C11A 1.395(4) C8A C9A 1.402(3) C8A C13A 1.403(3) C8A C7A 1.445(4) O1A C1A 1.233(3) C14A C5A 1.530(4) C14A H14E 0.9800 C14A H14D 0.9800 C14A H14F 0.9800 C2A C3A 1.344(4) C2A C1A 1.459(4) C2A H2A 0.9500 C3A C4A 1.512(4) C1A C6A 1.502(4) C7A C4A 1.557(4) C17A H17D 0.9800 C17A H17F 0.9800 C17A H17E 0.9800 C5A C6A 1.532(4) C5A C4A 1.532(4) C5A H5A 1.0000 C16A H16E 0.9800 C16A H16D 0.9800 C16A H16F 0.9800 C15A H15E 0.9800 C15A H15F 0.9800 C15A H15D 0.9800 C6A H6AA 0.9900 C6A H6AB 0.9900 Cl1 C12 1.728(3) O4 C7 1.219(3) O5 C11 1.354(3) O5 C16 1.444(4) C7 C8 1.441(4) C7 C4 1.554(4) O3 C13 1.362(3) O3 C4 1.464(3) O6 C9 1.347(3) O6 C17 1.444(3) O2 C3 1.342(3) O2 C15 1.452(4) C2 C3 1.351(4) C2 C1 1.441(4) C2 H2 0.9500 C10 C9 1.387(4) C10 C11 1.402(4) C10 H10 0.9500 O1 C1 1.230(3) C12 C13 1.378(4) C12 C11 1.401(4) C9 C8 1.411(4) C13 C8 1.396(3) C1 C6 1.511(4) C6 C5 1.527(4) C6 H6A 0.9900 C6 H6B 0.9900 C17 H17A 0.9800 C17 H17B 0.9800 C17 H17C 0.9800 C3 C4 1.507(4) C5 C14 1.519(4) C5 C4 1.539(4) C5 H6 1.0000 C14 H14A 0.9800 C14 H14B 0.9800 C14 H14C 0.9800 C15 H15A 0.9800 C15 H15B 0.9800 C15 H15C 0.9800 C16 H16A 0.9800 C16 H16B 0.9800 C16 H16C 0.9800 N1 O7 1.218(4) N1 O8 1.228(4) N1 C18 1.493(4) C18 C19 1.494(4) C18 H18A 0.9900 C18 H18B 0.9900 C19 H19A 0.9800 C19 H19B 0.9800 C19 H19C 0.9800