#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:49:58 +0100 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/89/2238923.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_2238923
loop_
_publ_author_name
'Yamuna, Thammarse S.'
'Jasinski, Jerry P.'
'Anderson, Brian J.'
'Yathirajan, H. S.'
'Kaur, Manpreet'
_publ_section_title
;
Raltegravir monohydrate
;
_journal_coeditor_code SJ5363
_journal_issue 12
_journal_name_full 'Acta Crystallographica Section E'
_journal_page_first o1743
_journal_page_last o1744
_journal_paper_doi 10.1107/S1600536813029747
_journal_volume 69
_journal_year 2013
_chemical_formula_iupac 'C20 H21 F N6 O5, H2 O'
_chemical_formula_moiety 'C20 H21 F N6 O5, H2 O'
_chemical_formula_sum 'C20 H23 F N6 O6'
_chemical_formula_weight 462.44
_chemical_name_common
;
Raltegravir monohydrate
;
_chemical_name_systematic
'N-(4-fluorobenzyl)-5-hydroxy-1-methyl-2-{1-methyl-1-[(5-methyl-1,3,4-oxadiazol-2-ylcarbonyl)amino]ethyl}-6-oxo-1,6-dihydropyrimidine-4-carboxamide monohydrate'
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_Hall '-P 1'
_space_group_name_H-M_alt 'P -1'
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary direct
_audit_creation_method
;
Olex2 1.2
(compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha 110.481(7)
_cell_angle_beta 108.093(7)
_cell_angle_gamma 92.329(6)
_cell_formula_units_Z 2
_cell_length_a 8.3860(6)
_cell_length_b 11.8610(9)
_cell_length_c 12.1102(9)
_cell_measurement_reflns_used 3215
_cell_measurement_temperature 173(2)
_cell_measurement_theta_max 32.8784
_cell_measurement_theta_min 3.0431
_cell_volume 1057.43(16)
_computing_cell_refinement 'CrysAlis PRO (Agilent, 2012)'
_computing_data_collection 'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction 'CrysAlis RED (Agilent, 2012)'
_computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material 'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'SHELXL2012 (Sheldrick, 2008)'
_computing_structure_solution 'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature 173(2)
_diffrn_detector_area_resol_mean 16.0416
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measurement_device_type 'Agilent Xcalibur (Eos, Gemini)'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0253
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 17
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_number 12734
_diffrn_reflns_theta_full 26.000
_diffrn_reflns_theta_max 32.953
_diffrn_reflns_theta_min 3.049
_exptl_absorpt_coefficient_mu 0.115
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.89026
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO and CrysAlis RED; Agilent, 2012)
;
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.452
_exptl_crystal_description irregular
_exptl_crystal_F_000 484
_exptl_crystal_size_max 0.44
_exptl_crystal_size_mid 0.32
_exptl_crystal_size_min 0.26
_refine_diff_density_max 0.783
_refine_diff_density_min -0.393
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.028
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 306
_refine_ls_number_reflns 7007
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.028
_refine_ls_R_factor_all 0.0932
_refine_ls_R_factor_gt 0.0674
_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^)+(0.0974P)^2^+0.6433P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1824
_refine_ls_wR_factor_ref 0.2060
_reflns_number_gt 5042
_reflns_number_total 7007
_reflns_threshold_expression I>2\s(I)
_iucr_refine_instructions_details
;
TITL HSY-623B in P-1 #2
CELL 0.71073 8.38604 11.86096 12.11024 110.4813 108.0927 92.3291
ZERR 2 0.00064 0.00088 0.00089 0.0068 0.0068 0.0062
LATT 1
SFAC C H N O F
UNIT 40 46 12 12 2
EQIV $1 2-X,-Y,1-Z
EQIV $2 2-X,1-Y,1-Z
EQIV $3 2-X,-Y,2-Z
EQIV $4 2-X,1-Y,2-Z
EQIV $5 1-X,-Y,1-Z
EQIV $6 1-X,-Y,-Z
EQIV $7 +X,1+Y,+Z
L.S. 25
PLAN 15
TEMP -100(2)
HTAB O4 O5
HTAB N1 O5_$1
HTAB N4 O1W_$2
HTAB C7 O1W_$2
HTAB C10 O5_$3
HTAB C19 F1_$4
HTAB C20 O4_$5
HTAB C20 N1
HTAB C20 N6_$6
HTAB O1W O2
HTAB O1W O3_$7
HTAB O1W O4_$7
REM reset to P-1 #2
BOND $H
MORE -1
fmap 2
acta 52
CONF
OMIT 1 -7 2
OMIT -2 5 1
OMIT -2 -3 1
OMIT 4 3 0
OMIT -1 -3 2
OMIT 4 -4 3
OMIT 1 -2 1
OMIT -2 3 0
REM J:/yathirajan%202013/HSY-623B-jpjMK/HSY-623B.hkl
WGHT 0.097400 0.643300
FVAR 7.49247
F1 5 1.155448 0.336877 1.316367 11.00000 0.07812 0.06427 =
0.03102 0.01031 0.02590 0.02816
O1 4 0.778486 0.365325 0.099014 11.00000 0.06112 0.03018 =
0.03256 0.01483 0.01385 0.00376
O2 4 0.712148 0.447188 0.326789 11.00000 0.05906 0.02296 =
0.03624 0.01411 0.01139 0.01161
O3 4 0.505674 -0.133264 0.346263 11.00000 0.03027 0.02906 =
0.04342 0.01464 0.00753 -0.00003
O4 4 0.768546 -0.164757 0.521104 11.00000 0.03789 0.02497 =
0.03902 0.01773 0.01423 0.00936
AFIX 147
H4 2 0.856990 -0.162854 0.578894 11.00000 -1.50000
AFIX 0
O5 4 1.049932 -0.057428 0.707619 11.00000 0.03905 0.03306 =
0.03194 0.01994 0.01516 0.01679
N1 3 0.753986 0.261426 0.338681 11.00000 0.03732 0.02205 =
0.02580 0.01174 0.01170 0.00950
AFIX 43
H1 2 0.766118 0.187538 0.295013 11.00000 -1.20000
AFIX 0
N2 3 0.624434 0.065429 0.401890 11.00000 0.02222 0.02344 =
0.02141 0.00866 0.00826 0.00660
N3 3 0.878752 0.155469 0.573173 11.00000 0.02632 0.02352 =
0.02078 0.00992 0.00888 0.00809
N4 3 1.148726 0.142337 0.760909 11.00000 0.03082 0.03351 =
0.02243 0.01395 0.00762 0.01041
AFIX 43
H4A 2 1.133353 0.206890 0.741398 11.00000 -1.20000
AFIX 0
N5 3 0.726865 0.177371 0.085755 11.00000 0.04313 0.02947 =
0.02758 0.01274 0.00501 0.00600
N6 3 0.747470 0.173214 -0.028281 11.00000 0.05209 0.03884 =
0.03057 0.01284 0.00595 0.00757
C1 1 0.754581 0.286350 0.467150 11.00000 0.02773 0.02098 =
0.02308 0.00961 0.00761 0.00798
C2 1 0.753148 0.163069 0.482640 11.00000 0.02366 0.02059 =
0.02087 0.00778 0.01002 0.00704
C3 1 0.622052 -0.046880 0.414743 11.00000 0.02606 0.02385 =
0.02753 0.01053 0.01330 0.00639
C4 1 0.767679 -0.054802 0.513627 11.00000 0.02844 0.02354 =
0.02642 0.01226 0.01536 0.00992
C5 1 0.886581 0.046418 0.589239 11.00000 0.02674 0.02475 =
0.02013 0.01093 0.01152 0.01040
C6 1 1.035995 0.041081 0.691733 11.00000 0.03077 0.03047 =
0.02098 0.01330 0.01460 0.01400
C7 1 1.298341 0.152144 0.868741 11.00000 0.02871 0.04549 =
0.02608 0.01657 0.00666 0.01255
AFIX 23
H7A 2 1.395121 0.206229 0.873129 11.00000 -1.20000
H7B 2 1.330584 0.070460 0.856754 11.00000 -1.20000
AFIX 0
C8 1 1.264189 0.202298 0.990298 11.00000 0.02633 0.02949 =
0.02246 0.01094 0.00301 0.00760
C9 1 1.188252 0.125344 1.029766 11.00000 0.03558 0.02579 =
0.02548 0.00783 0.00725 0.00370
AFIX 43
H9 2 1.161869 0.040117 0.980993 11.00000 -1.20000
AFIX 0
C10 1 1.149766 0.170085 1.139229 11.00000 0.03385 0.03769 =
0.02821 0.01393 0.00907 0.00427
AFIX 43
H10 2 1.095873 0.117036 1.165184 11.00000 -1.20000
AFIX 0
C11 1 1.191911 0.292797 1.208323 11.00000 0.04391 0.04079 =
0.02332 0.00951 0.00954 0.01616
C12 1 1.271043 0.372287 1.174149 11.00000 0.08586 0.02586 =
0.03682 0.00326 0.01856 0.00827
AFIX 43
H12 2 1.300683 0.456978 1.225154 11.00000 -1.20000
AFIX 0
C13 1 1.306724 0.326369 1.063745 11.00000 0.06189 0.02969 =
0.03764 0.01373 0.01456 -0.00047
AFIX 43
H13 2 1.360444 0.380012 1.038323 11.00000 -1.20000
AFIX 0
C14 1 0.736355 0.342817 0.283197 11.00000 0.03663 0.02430 =
0.02702 0.01288 0.00589 0.00463
C15 1 0.746493 0.289532 0.154033 11.00000 0.03645 0.02671 =
0.02920 0.01455 0.00544 0.00355
C16 1 0.776584 0.285709 -0.015323 11.00000 0.04082 0.04073 =
0.02885 0.01264 0.00561 0.00219
C17 1 0.809162 0.333796 -0.104856 11.00000 0.07952 0.05751 =
0.04257 0.02529 0.01685 0.00244
AFIX 137
H17A 2 0.714817 0.374094 -0.134893 11.00000 -1.50000
H17B 2 0.818972 0.266384 -0.176320 11.00000 -1.50000
H17C 2 0.915324 0.392830 -0.062785 11.00000 -1.50000
AFIX 0
C18 1 0.601495 0.344307 0.492088 11.00000 0.03337 0.02930 =
0.03738 0.01089 0.01465 0.01415
AFIX 137
H18A 2 0.620793 0.431073 0.506252 11.00000 -1.50000
H18B 2 0.588540 0.335780 0.566611 11.00000 -1.50000
H18C 2 0.497887 0.302892 0.419245 11.00000 -1.50000
AFIX 0
C19 1 0.918354 0.373817 0.560343 11.00000 0.03221 0.02410 =
0.03427 0.01178 0.00408 0.00268
AFIX 137
H19A 2 1.016798 0.337474 0.546406 11.00000 -1.50000
H19B 2 0.923415 0.388868 0.646353 11.00000 -1.50000
H19C 2 0.919807 0.451165 0.547994 11.00000 -1.50000
AFIX 0
C20 1 0.476941 0.069945 0.298781 11.00000 0.02411 0.03074 =
0.02647 0.01135 0.00601 0.00610
AFIX 137
H20A 2 0.383688 0.093533 0.330019 11.00000 -1.50000
H20B 2 0.439556 -0.010690 0.230243 11.00000 -1.50000
H20C 2 0.509789 0.129986 0.267719 11.00000 -1.50000
AFIX 6
O1W 4 0.637687 0.637438 0.233223 11.00000 0.12148 0.03883 =
0.05189 0.02405 0.02417 0.03086
H1WA 2 0.625498 0.690012 0.297666 11.00000 -1.50000
H1WB 2 0.663039 0.574089 0.247775 11.00000 -1.50000
AFIX 0
HKLF 4
REM HSY-623B in P-1 #2
REM R1 = 0.0674 for 5042 Fo > 4sig(Fo) and 0.0932 for all 7007 data
REM 306 parameters refined using 0 restraints
END
WGHT 0.0974 0.6432
REM Highest difference peak 0.783, deepest hole -0.393, 1-sigma level 0.070
Q1 1 0.6576 0.3792 0.0917 11.00000 0.05 0.78
Q2 1 0.8414 0.4042 -0.0160 11.00000 0.05 0.77
Q3 1 0.6860 0.3597 -0.0159 11.00000 0.05 0.74
Q4 1 0.8735 0.3600 -0.1431 11.00000 0.05 0.68
Q5 1 0.9528 0.4516 0.0931 11.00000 0.05 0.65
Q6 1 0.9209 0.4972 0.0714 11.00000 0.05 0.47
Q7 1 0.5351 0.6010 0.2271 11.00000 0.05 0.44
Q8 1 0.8243 -0.0060 0.5489 11.00000 0.05 0.44
Q9 1 0.6959 -0.0571 0.4616 11.00000 0.05 0.42
Q10 1 0.6257 0.4423 0.3338 11.00000 0.05 0.37
Q11 1 0.8376 0.3277 0.5116 11.00000 0.05 0.36
Q12 1 1.2873 0.2587 1.0268 11.00000 0.05 0.34
Q13 1 0.9617 0.0462 0.6418 11.00000 0.05 0.34
Q14 1 0.7655 0.2317 0.4860 11.00000 0.05 0.32
Q15 1 0.7796 0.2296 0.1313 11.00000 0.05 0.32
;
_cod_data_source_file sj5363.cif
_cod_data_source_block I
_cod_original_cell_volume 1057.44(15)
_cod_database_code 2238923
#BEGIN Tags that were not found in dictionaries:
_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_hkl_checksum 31717
_shelx_res_checksum 66418
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_occupancy
F F1 1.1554(2) 0.33688(15) 1.31637(13) 0.0578(4) Uani d 1
O O1 0.7785(2) 0.36533(14) 0.09901(14) 0.0412(4) Uani d 1
O O2 0.7121(2) 0.44719(13) 0.32679(14) 0.0398(4) Uani d 1
O O3 0.50567(19) -0.13326(13) 0.34626(15) 0.0355(3) Uani d 1
O O4 0.76855(19) -0.16476(12) 0.52110(14) 0.0320(3) Uani d 1
H H4 0.8570 -0.1629 0.5789 0.048 Uiso calc 1
O O5 1.04993(19) -0.05743(13) 0.70762(13) 0.0315(3) Uani d 1
N N1 0.7540(2) 0.26143(14) 0.33868(14) 0.0273(3) Uani d 1
H H1 0.7661 0.1875 0.2950 0.033 Uiso calc 1
N N2 0.62443(18) 0.06543(13) 0.40189(13) 0.0221(3) Uani d 1
N N3 0.87875(19) 0.15547(13) 0.57317(13) 0.0228(3) Uani d 1
N N4 1.1487(2) 0.14234(15) 0.76091(14) 0.0282(3) Uani d 1
H H4A 1.1334 0.2069 0.7414 0.034 Uiso calc 1
N N5 0.7269(2) 0.17737(16) 0.08576(16) 0.0347(4) Uani d 1
N N6 0.7475(3) 0.17321(18) -0.02828(18) 0.0427(5) Uani d 1
C C1 0.7546(2) 0.28635(15) 0.46715(16) 0.0238(3) Uani d 1
C C2 0.7531(2) 0.16307(15) 0.48264(15) 0.0211(3) Uani d 1
C C3 0.6221(2) -0.04688(16) 0.41474(17) 0.0245(3) Uani d 1
C C4 0.7677(2) -0.05480(15) 0.51363(16) 0.0237(3) Uani d 1
C C5 0.8866(2) 0.04642(15) 0.58924(15) 0.0222(3) Uani d 1
C C6 1.0360(2) 0.04108(16) 0.69173(16) 0.0247(3) Uani d 1
C C7 1.2983(3) 0.1521(2) 0.86874(18) 0.0331(4) Uani d 1
H H7A 1.3951 0.2062 0.8731 0.040 Uiso calc 1
H H7B 1.3306 0.0705 0.8568 0.040 Uiso calc 1
C C8 1.2642(2) 0.20230(17) 0.99030(17) 0.0271(4) Uani d 1
C C9 1.1883(3) 0.12534(17) 1.02977(18) 0.0304(4) Uani d 1
H H9 1.1619 0.0401 0.9810 0.036 Uiso calc 1
C C10 1.1498(3) 0.17008(19) 1.13923(19) 0.0333(4) Uani d 1
H H10 1.0959 0.1170 1.1652 0.040 Uiso calc 1
C C11 1.1919(3) 0.2928(2) 1.20832(18) 0.0370(5) Uani d 1
C C12 1.2710(4) 0.3723(2) 1.1741(2) 0.0527(7) Uani d 1
H H12 1.3007 0.4570 1.2252 0.063 Uiso calc 1
C C13 1.3067(4) 0.3264(2) 1.0637(2) 0.0438(5) Uani d 1
H H13 1.3604 0.3800 1.0383 0.053 Uiso calc 1
C C14 0.7364(3) 0.34282(17) 0.28320(18) 0.0297(4) Uani d 1
C C15 0.7465(3) 0.28953(17) 0.15403(18) 0.0312(4) Uani d 1
C C16 0.7766(3) 0.2857(2) -0.0153(2) 0.0388(5) Uani d 1
C C17 0.8092(5) 0.3338(3) -0.1049(3) 0.0595(7) Uani d 1
H H17A 0.7148 0.3741 -0.1349 0.089 Uiso calc 1
H H17B 0.8190 0.2664 -0.1763 0.089 Uiso calc 1
H H17C 0.9153 0.3928 -0.0628 0.089 Uiso calc 1
C C18 0.6015(3) 0.34431(18) 0.4921(2) 0.0330(4) Uani d 1
H H18A 0.6208 0.4311 0.5063 0.049 Uiso calc 1
H H18B 0.5885 0.3358 0.5666 0.049 Uiso calc 1
H H18C 0.4979 0.3029 0.4192 0.049 Uiso calc 1
C C19 0.9184(3) 0.37382(17) 0.56034(19) 0.0319(4) Uani d 1
H H19A 1.0168 0.3375 0.5464 0.048 Uiso calc 1
H H19B 0.9234 0.3889 0.6464 0.048 Uiso calc 1
H H19C 0.9198 0.4512 0.5480 0.048 Uiso calc 1
C C20 0.4769(2) 0.06994(17) 0.29878(17) 0.0276(4) Uani d 1
H H20A 0.3837 0.0935 0.3300 0.041 Uiso calc 1
H H20B 0.4396 -0.0107 0.2302 0.041 Uiso calc 1
H H20C 0.5098 0.1300 0.2677 0.041 Uiso calc 1
O O1W 0.6377(4) 0.63744(18) 0.2332(2) 0.0697(7) Uani d 1
H H1WA 0.6255 0.6900 0.2977 0.105 Uiso d 1
H H1WB 0.6630 0.5741 0.2478 0.105 Uiso d 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
F1 0.0781(11) 0.0643(10) 0.0310(7) 0.0282(8) 0.0259(7) 0.0103(7)
O1 0.0611(10) 0.0302(7) 0.0326(7) 0.0038(7) 0.0138(7) 0.0148(6)
O2 0.0591(10) 0.0230(7) 0.0362(8) 0.0116(6) 0.0114(7) 0.0141(6)
O3 0.0303(7) 0.0291(7) 0.0434(8) 0.0000(5) 0.0075(6) 0.0146(6)
O4 0.0379(7) 0.0250(6) 0.0390(8) 0.0094(5) 0.0142(6) 0.0177(6)
O5 0.0391(7) 0.0331(7) 0.0319(7) 0.0168(6) 0.0152(6) 0.0199(6)
N1 0.0373(8) 0.0221(7) 0.0258(7) 0.0095(6) 0.0117(6) 0.0117(6)
N2 0.0222(6) 0.0234(7) 0.0214(6) 0.0066(5) 0.0083(5) 0.0087(5)
N3 0.0263(7) 0.0235(7) 0.0208(6) 0.0081(5) 0.0089(5) 0.0099(5)
N4 0.0308(8) 0.0335(8) 0.0224(7) 0.0104(6) 0.0076(6) 0.0139(6)
N5 0.0431(10) 0.0295(8) 0.0276(8) 0.0060(7) 0.0050(7) 0.0127(6)
N6 0.0521(11) 0.0388(10) 0.0306(9) 0.0076(8) 0.0060(8) 0.0128(7)
C1 0.0277(8) 0.0210(7) 0.0231(7) 0.0080(6) 0.0076(6) 0.0096(6)
C2 0.0237(7) 0.0206(7) 0.0209(7) 0.0070(6) 0.0100(6) 0.0078(6)
C3 0.0261(8) 0.0239(8) 0.0275(8) 0.0064(6) 0.0133(7) 0.0105(6)
C4 0.0284(8) 0.0235(8) 0.0264(8) 0.0099(6) 0.0154(7) 0.0123(6)
C5 0.0267(8) 0.0247(8) 0.0201(7) 0.0104(6) 0.0115(6) 0.0109(6)
C6 0.0308(8) 0.0305(8) 0.0210(7) 0.0140(7) 0.0146(7) 0.0133(6)
C7 0.0287(9) 0.0455(11) 0.0261(8) 0.0126(8) 0.0067(7) 0.0166(8)
C8 0.0263(8) 0.0295(9) 0.0225(8) 0.0076(7) 0.0030(6) 0.0109(7)
C9 0.0356(9) 0.0258(8) 0.0255(8) 0.0037(7) 0.0072(7) 0.0078(7)
C10 0.0339(10) 0.0377(10) 0.0282(9) 0.0043(8) 0.0091(8) 0.0139(8)
C11 0.0439(11) 0.0408(11) 0.0233(8) 0.0162(9) 0.0095(8) 0.0095(8)
C12 0.086(2) 0.0259(10) 0.0368(12) 0.0083(11) 0.0186(12) 0.0033(9)
C13 0.0619(15) 0.0297(10) 0.0376(11) -0.0005(10) 0.0146(10) 0.0137(9)
C14 0.0366(9) 0.0243(8) 0.0270(8) 0.0046(7) 0.0059(7) 0.0129(7)
C15 0.0365(10) 0.0267(9) 0.0292(9) 0.0036(7) 0.0054(7) 0.0146(7)
C16 0.0408(11) 0.0407(11) 0.0289(9) 0.0022(9) 0.0056(8) 0.0126(8)
C17 0.080(2) 0.0575(16) 0.0426(13) 0.0024(14) 0.0169(13) 0.0253(12)
C18 0.0334(9) 0.0293(9) 0.0374(10) 0.0141(7) 0.0147(8) 0.0109(8)
C19 0.0322(9) 0.0241(8) 0.0343(9) 0.0027(7) 0.0041(8) 0.0118(7)
C20 0.0241(8) 0.0307(9) 0.0265(8) 0.0061(7) 0.0060(7) 0.0113(7)
O1W 0.121(2) 0.0388(10) 0.0519(11) 0.0309(12) 0.0242(13) 0.0241(9)
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'
F F 0.0171 0.0103 '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
C15 O1 C16 102.68(16)
C4 O4 H4 109.5
C1 N1 H1 117.4
C14 N1 H1 117.4
C14 N1 C1 125.12(15)
C2 N2 C3 121.45(14)
C2 N2 C20 124.45(14)
C3 N2 C20 114.08(14)
C2 N3 C5 119.27(15)
C6 N4 H4A 118.4
C6 N4 C7 123.12(16)
C7 N4 H4A 118.4
C15 N5 N6 106.18(17)
C16 N6 N5 105.55(18)
N1 C1 C2 106.42(13)
N1 C1 C18 113.17(14)
N1 C1 C19 108.21(15)
C2 C1 C18 110.32(15)
C19 C1 C2 110.05(14)
C19 C1 C18 108.63(15)
N2 C2 C1 120.93(14)
N3 C2 N2 122.32(15)
N3 C2 C1 116.75(15)
O3 C3 N2 122.18(16)
O3 C3 C4 122.56(16)
N2 C3 C4 115.25(15)
O4 C4 C3 114.82(16)
O4 C4 C5 126.23(16)
C5 C4 C3 118.95(15)
N3 C5 C6 117.28(15)
C4 C5 N3 122.65(15)
C4 C5 C6 120.04(15)
O5 C6 N4 123.62(16)
O5 C6 C5 119.27(17)
N4 C6 C5 117.11(15)
N4 C7 H7A 109.3
N4 C7 H7B 109.3
N4 C7 C8 111.60(16)
H7A C7 H7B 108.0
C8 C7 H7A 109.3
C8 C7 H7B 109.3
C9 C8 C7 120.34(17)
C9 C8 C13 119.05(19)
C13 C8 C7 120.60(19)
C8 C9 H9 119.3
C8 C9 C10 121.39(18)
C10 C9 H9 119.3
C9 C10 H10 121.1
C11 C10 C9 117.9(2)
C11 C10 H10 121.1
F1 C11 C10 118.0(2)
F1 C11 C12 119.3(2)
C10 C11 C12 122.7(2)
C11 C12 H12 120.6
C11 C12 C13 118.7(2)
C13 C12 H12 120.6
C8 C13 H13 119.9
C12 C13 C8 120.2(2)
C12 C13 H13 119.9
O2 C14 N1 126.78(19)
O2 C14 C15 121.48(17)
N1 C14 C15 111.74(16)
O1 C15 C14 119.28(17)
N5 C15 O1 113.46(18)
N5 C15 C14 127.26(17)
O1 C16 C17 119.6(2)
N6 C16 O1 112.1(2)
N6 C16 C17 128.3(2)
C16 C17 H17A 109.5
C16 C17 H17B 109.5
C16 C17 H17C 109.5
H17A C17 H17B 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C1 C18 H18A 109.5
C1 C18 H18B 109.5
C1 C18 H18C 109.5
H18A C18 H18B 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C1 C19 H19A 109.5
C1 C19 H19B 109.5
C1 C19 H19C 109.5
H19A C19 H19B 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
N2 C20 H20A 109.5
N2 C20 H20B 109.5
N2 C20 H20C 109.5
H20A C20 H20B 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
H1WA O1W H1WB 109.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C11 1.364(2)
O1 C15 1.355(2)
O1 C16 1.371(3)
O2 C14 1.217(2)
O3 C3 1.229(2)
O4 H4 0.8400
O4 C4 1.339(2)
O5 C6 1.253(2)
N1 H1 0.8800
N1 C1 1.477(2)
N1 C14 1.345(2)
N2 C2 1.383(2)
N2 C3 1.394(2)
N2 C20 1.478(2)
N3 C2 1.296(2)
N3 C5 1.375(2)
N4 H4A 0.8800
N4 C6 1.323(3)
N4 C7 1.469(2)
N5 N6 1.429(3)
N5 C15 1.268(3)
N6 C16 1.291(3)
C1 C2 1.538(2)
C1 C18 1.542(3)
C1 C19 1.529(3)
C3 C4 1.454(2)
C4 C5 1.357(3)
C5 C6 1.487(2)
C7 H7A 0.9900
C7 H7B 0.9900
C7 C8 1.505(3)
C8 C9 1.384(3)
C8 C13 1.389(3)
C9 H9 0.9500
C9 C10 1.389(3)
C10 H10 0.9500
C10 C11 1.366(3)
C11 C12 1.376(4)
C12 H12 0.9500
C12 C13 1.388(4)
C13 H13 0.9500
C14 C15 1.500(3)
C16 C17 1.476(4)
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
O1W H1WA 0.8500
O1W H1WB 0.8504
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O4 H4 O5 . 0.84 1.88 2.593(2) 142.6
O1W H1WB O2 . 0.85 2.04 2.869(2) 164.4
C20 H20C N1 . 0.98 2.25 2.982(3) 130.4
N1 H1 O5 2_756 0.88 2.23 2.970(2) 142.2
N4 H4A O1W 2_766 0.88 2.48 3.074(3) 125.5
C7 H7A O1W 2_766 0.99 2.58 3.240(3) 124.0
C10 H10 O5 2_757 0.95 2.50 3.393(3) 157.5
C20 H20A O4 2_656 0.98 2.46 3.394(2) 159.5
C20 H20B N6 2_655 0.98 2.50 3.422(3) 157.5
O1W H1WA O4 1_565 0.85 2.51 3.249(3) 146.4
O1W H1WA O3 1_565 0.85 2.33 3.013(3) 137.7
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
F1 C11 C12 C13 -179.7(2)
O2 C14 C15 O1 19.2(3)
O2 C14 C15 N5 -160.2(2)
O3 C3 C4 O4 2.5(3)
O3 C3 C4 C5 -176.74(17)
O4 C4 C5 N3 178.19(16)
O4 C4 C5 C6 0.3(3)
N1 C1 C2 N2 -57.7(2)
N1 C1 C2 N3 121.37(16)
N1 C14 C15 O1 -161.84(18)
N1 C14 C15 N5 18.8(3)
N2 C3 C4 O4 -176.77(15)
N2 C3 C4 C5 4.0(2)
N3 C5 C6 O5 -178.36(15)
N3 C5 C6 N4 1.0(2)
N4 C7 C8 C9 85.1(2)
N4 C7 C8 C13 -94.3(2)
N5 N6 C16 O1 0.5(3)
N5 N6 C16 C17 179.3(3)
N6 N5 C15 O1 0.2(2)
N6 N5 C15 C14 179.65(19)
C1 N1 C14 O2 -2.9(3)
C1 N1 C14 C15 178.28(17)
C2 N2 C3 O3 177.59(16)
C2 N2 C3 C4 -3.1(2)
C2 N3 C5 C4 0.1(2)
C2 N3 C5 C6 178.05(15)
C3 N2 C2 N3 0.8(2)
C3 N2 C2 C1 179.79(15)
C3 C4 C5 N3 -2.7(3)
C3 C4 C5 C6 179.50(15)
C4 C5 C6 O5 -0.4(2)
C4 C5 C6 N4 178.97(16)
C5 N3 C2 N2 0.9(2)
C5 N3 C2 C1 -178.19(14)
C6 N4 C7 C8 -94.3(2)
C7 N4 C6 O5 -3.5(3)
C7 N4 C6 C5 177.18(16)
C7 C8 C9 C10 -177.60(18)
C7 C8 C13 C12 178.4(2)
C8 C9 C10 C11 -1.1(3)
C9 C8 C13 C12 -0.9(4)
C9 C10 C11 F1 -179.51(18)
C9 C10 C11 C12 -0.4(3)
C10 C11 C12 C13 1.2(4)
C11 C12 C13 C8 -0.5(4)
C13 C8 C9 C10 1.8(3)
C14 N1 C1 C2 172.40(17)
C14 N1 C1 C18 51.1(2)
C14 N1 C1 C19 -69.4(2)
C15 O1 C16 N6 -0.3(3)
C15 O1 C16 C17 -179.2(2)
C15 N5 N6 C16 -0.4(2)
C16 O1 C15 N5 0.1(2)
C16 O1 C15 C14 -179.43(18)
C18 C1 C2 N2 65.4(2)
C18 C1 C2 N3 -115.50(17)
C19 C1 C2 N2 -174.73(15)
C19 C1 C2 N3 4.3(2)
C20 N2 C2 N3 178.83(16)
C20 N2 C2 C1 -2.2(2)
C20 N2 C3 O3 -0.6(2)
C20 N2 C3 C4 178.63(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139086253