#------------------------------------------------------------------------------
#$Date: 2024-07-25 04:55:56 +0300 (Thu, 25 Jul 2024) $
#$Revision: 293536 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/32/2023211.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_2023211
loop_
_publ_author_name
'Peng, Ziyu'
'Ye, Long'
_publ_section_title
;
 Comparison of the crystal structures of the JAK1/2 inhibitor ruxolitinib
 and its hydrate and phosphate
;
_journal_coeditor_code           OJ3020
_journal_issue                   8
_journal_name_full
'Acta Crystallographica Section C Structural Chemistry'
_journal_paper_doi               10.1107/S2053229624006740
_journal_volume                  80
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_iupac          'C17 H19 N6 +, H2 P O4 -'
_chemical_formula_moiety         'C17 H19 N6 +, H2 O4 P -'
_chemical_formula_sum            'C17 H21 N6 O4 P'
_chemical_formula_weight         404.37
_chemical_name_systematic
'4-{1-[(1R)-2-Cyano-1-cyclopentylethyl]-1H-pyrazol-4-yl}-7H-pyrrolo[2,3-d]pyrimidin-3-ium dihydrogen phosphate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.1398(4)
_cell_length_b                   12.0894(6)
_cell_length_c                   43.818(2)
_cell_measurement_reflns_used    9334
_cell_measurement_temperature    296
_cell_measurement_theta_max      55.459
_cell_measurement_theta_min      3.299
_cell_volume                     3782.2(3)
_computing_cell_refinement
;
SAINT-Plus (Bruker, 2016)
;
_computing_data_collection
;
SMART (Bruker, 2016)
;
_computing_data_reduction
;
SAINT-Plus (Bruker, 2016)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009) and
DIAMOND (Pennington, 1999)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)  and
Mercury (Macrae et al.,  2020)
;
_computing_structure_refinement
;
SHELXL2019 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_number            84024
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.530
_diffrn_reflns_theta_min         3.299
_diffrn_source_current           3.57
_diffrn_source_power             0.24954300000000
_diffrn_source_voltage           69.9
_exptl_absorpt_coefficient_mu    1.053
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_description       needle
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.314
_refine_ls_abs_structure_details
;
Flack x determined using 2547 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.044(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         8662
_refine_ls_number_restraints     191
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0418
_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/[σ²(Fo²)+(0.0717P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1130
_reflns_number_gt                6947
_reflns_number_total             8662
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            oj3020sup1.cif
_cod_data_source_block           rux-p
_cod_original_cell_volume        3782.2(4)
_cod_database_code               2023211
_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_min   0.893
_shelx_estimated_absorpt_t_max   0.979
loop_
_space_group_symop_operation_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1A 0.65649(11) 0.45547(6) 0.42726(2) 0.04229(19) Uani d 1 . .
O O1A 0.6066(3) 0.54089(16) 0.40388(5) 0.0514(5) Uani d 1 . .
O O2A 0.5943(4) 0.48670(18) 0.45935(5) 0.0560(6) Uani d 1 . .
O O3A 0.5760(4) 0.34235(18) 0.41825(5) 0.0548(6) Uani d 1 . .
H H3AA 0.494(4) 0.317(3) 0.4296(8) 0.082 Uiso d 1 . .
O O4A 0.8722(3) 0.4475(2) 0.42736(7) 0.0727(8) Uani d 1 . .
H H4A 0.905636 0.402615 0.440290 0.109 Uiso calc 1 . .
P P1B 0.21366(10) 0.30897(6) 0.47465(2) 0.03782(17) Uani d 1 . .
O O1B 0.3300(3) 0.24909(15) 0.45067(4) 0.0449(5) Uani d 1 . .
O O2B 0.2951(3) 0.42237(17) 0.48157(5) 0.0519(5) Uani d 1 . .
H H2BA 0.381(4) 0.449(3) 0.4712(8) 0.078 Uiso d 1 . .
O O3B 0.0103(3) 0.31624(19) 0.46592(5) 0.0537(5) Uani d 1 . .
O O4B 0.2128(3) 0.2396(2) 0.50465(5) 0.0537(5) Uani d 1 . .
H H4B 0.319855 0.219606 0.508604 0.081 Uiso calc 1 . .
N N1A 0.8069(4) 1.03408(19) 0.45525(6) 0.0470(6) Uani d 1 . .
H H1A 0.828444 1.054736 0.473701 0.056 Uiso calc 1 . .
C C1A 0.7998(5) 1.1024(2) 0.43002(7) 0.0514(7) Uani d 1 . .
H H1AA 0.815717 1.178725 0.430489 0.062 Uiso calc 1 . .
N N2A 0.7629(4) 0.84118(19) 0.46466(5) 0.0467(6) Uani d 1 . .
C C2A 0.7663(5) 1.0423(2) 0.40451(7) 0.0472(7) Uani d 1 . .
H H2A 0.756075 1.069027 0.384669 0.057 Uiso calc 1 . .
N N3A 0.6946(3) 0.73956(18) 0.41971(5) 0.0418(5) Uani d 1 . .
H H3A 0.666753 0.675849 0.412256 0.050 Uiso calc 1 . .
C C3A 0.7499(4) 0.9295(2) 0.41416(6) 0.0388(6) Uani d 1 . .
N N4A 0.5699(5) 0.7373(2) 0.32401(6) 0.0634(8) Uani d 1 . .
C C4A 0.7743(4) 0.9295(2) 0.44602(6) 0.0408(6) Uani d 1 . .
N N5A 0.6691(4) 0.8315(2) 0.31873(5) 0.0501(6) Uani d 1 . .
C C5A 0.7229(5) 0.7489(2) 0.44995(6) 0.0461(7) Uani d 1 . .
H H5A 0.713479 0.684635 0.461509 0.055 Uiso calc 1 . .
N N6A 0.4936(9) 0.9492(4) 0.21840(9) 0.1197(19) Uani d 1 . .
C C6A 0.7086(4) 0.8276(2) 0.40058(6) 0.0380(6) Uani d 1 . .
C C7A 0.6785(4) 0.8103(2) 0.36838(6) 0.0413(6) Uani d 1 . .
C C8A 0.5788(5) 0.7231(3) 0.35413(7) 0.0566(9) Uani d 1 . .
H H8A 0.526349 0.663526 0.364482 0.068 Uiso calc 1 . .
C C9A 0.7336(5) 0.8773(2) 0.34439(6) 0.0447(6) Uani d 1 . .
H H9A 0.802701 0.942331 0.345869 0.054 Uiso calc 1 . .
C C10A 0.6929(5) 0.8715(3) 0.28734(7) 0.0527(8) Uani d 1 . .
H H10C 0.750266 0.944981 0.288622 0.063 Uiso calc 1 . .
C C11A 0.4956(6) 0.8873(4) 0.27458(8) 0.0668(10) Uani d 1 . .
H H11C 0.428013 0.817890 0.276149 0.080 Uiso calc 1 . .
H H11D 0.430106 0.941503 0.286912 0.080 Uiso calc 1 . .
C C12A 0.4943(7) 0.9235(4) 0.24290(9) 0.0769(12) Uani d 1 . .
C C13A 0.8203(6) 0.8007(3) 0.26771(8) 0.0653(9) Uani d 1 . .
H H13A 0.844244 0.842837 0.249014 0.078 Uiso calc 1 . .
C C14A 0.7510(7) 0.6881(4) 0.25778(11) 0.0862(13) Uani d 1 . .
H H14C 0.671000 0.694403 0.239972 0.103 Uiso calc 1 . .
H H14D 0.681059 0.652733 0.274053 0.103 Uiso calc 1 . .
C C15A 0.9283(10) 0.6222(5) 0.25026(16) 0.123(2) Uani d 1 . .
H H15C 0.921848 0.549309 0.259430 0.148 Uiso calc 1 . .
H H15D 0.940692 0.613606 0.228343 0.148 Uiso calc 1 . .
C C16A 1.0900(9) 0.6840(6) 0.26258(15) 0.121(2) Uani d 1 . .
H H16C 1.165174 0.713739 0.246072 0.145 Uiso calc 1 . .
H H16D 1.168081 0.635634 0.274843 0.145 Uiso calc 1 . .
C C17A 1.0113(6) 0.7771(4) 0.28205(12) 0.0894(13) Uani d 1 . .
H H17C 1.091281 0.841934 0.281168 0.107 Uiso calc 1 . .
H H17D 0.998183 0.754196 0.303150 0.107 Uiso calc 1 . .
N N1B 0.2387(4) -0.2951(2) 0.46540(7) 0.0579(7) Uani d 1 . .
H H1B 0.245886 -0.333642 0.481847 0.069 Uiso calc 1 . .
C C1B 0.1951(5) -0.3349(3) 0.43719(9) 0.0613(9) Uani d 1 . .
H H1BA 0.169441 -0.408612 0.432853 0.074 Uiso calc 1 . .
N N2B 0.3140(5) -0.1196(2) 0.48662(6) 0.0565(7) Uani d 1 . .
C C2B 0.1944(5) -0.2521(3) 0.41632(8) 0.0538(8) Uani d 1 . .
H H2B 0.166616 -0.258422 0.395658 0.065 Uiso calc 1 . .
N N3B 0.3096(4) 0.02370(18) 0.45001(5) 0.0437(6) Uani d 1 . .
H H3B 0.323506 0.093495 0.446977 0.052 Uiso calc 1 . .
C C3B 0.2446(4) -0.1535(2) 0.43224(7) 0.0436(6) Uani d 1 . .
N N4B 0.2251(6) 0.0366(3) 0.34516(6) 0.0733(9) Uani d 1 . .
C C4B 0.2688(4) -0.1855(2) 0.46329(7) 0.0466(7) Uani d 1 . .
N N5B 0.2470(5) 0.1350(2) 0.35969(6) 0.0584(7) Uani d 1 . .
C C5B 0.3305(6) -0.0154(3) 0.47894(7) 0.0550(8) Uani d 1 . .
H H5B 0.358336 0.035204 0.494261 0.066 Uiso calc 1 . .
N N6B 0.6761(8) 0.1284(4) 0.31372(12) 0.1215(18) Uani d 1 . .
C C6B 0.2678(4) -0.0417(2) 0.42557(6) 0.0400(6) Uani d 1 . .
C C7B 0.2549(4) 0.0101(2) 0.39595(6) 0.0417(6) Uani d 1 . .
C C8B 0.2285(6) -0.0375(3) 0.36689(8) 0.0632(9) Uani d 1 . .
H H8B 0.215123 -0.113032 0.363552 0.076 Uiso calc 1 . .
C C9B 0.2651(5) 0.1216(3) 0.38945(7) 0.0516(8) Uani d 1 . .
H H9B 0.281796 0.177880 0.403652 0.062 Uiso calc 1 . .
C C10B 0.2655(7) 0.2388(4) 0.34224(9) 0.0811(13) Uani d 1 . .
H H10A 0.242871 0.214219 0.321251 0.097 Uiso calc 0.388(6) A 2
H H10B 0.216155 0.229527 0.321530 0.097 Uiso calc 0.612(6) A 1
C C11B 0.4702(8) 0.2727(3) 0.34127(10) 0.0904(16) Uani d 1 . .
H H11A 0.481001 0.343220 0.330875 0.109 Uiso calc 1 . .
H H11B 0.515437 0.282391 0.361971 0.109 Uiso calc 1 . .
C C12B 0.5875(8) 0.1917(4) 0.32576(10) 0.0865(14) Uani d 1 . .
C C13B 0.1702(13) 0.3396(5) 0.35836(18) 0.0632(19) Uani d 0.612(6) A 1
H H13B 0.204885 0.340211 0.379996 0.076 Uiso calc 0.612(6) A 1
C C14B 0.2067(12) 0.4547(5) 0.34448(19) 0.084(2) Uani d 0.612(6) A 1
H H14A 0.308344 0.491948 0.354978 0.101 Uiso calc 0.612(6) A 1
H H14B 0.237082 0.449126 0.322961 0.101 Uiso calc 0.612(6) A 1
C C15B 0.0201(19) 0.5161(9) 0.3493(3) 0.103(4) Uani d 0.612(6) A 1
H H15A 0.009438 0.543545 0.369986 0.124 Uiso calc 0.612(6) A 1
H H15B 0.008035 0.577597 0.335172 0.124 Uiso calc 0.612(6) A 1
C C16B -0.1270(15) 0.4270(9) 0.3428(3) 0.105(3) Uani d 0.612(6) A 1
H H16A -0.244098 0.444324 0.352922 0.126 Uiso calc 0.612(6) A 1
H H16B -0.149808 0.420502 0.321028 0.126 Uiso calc 0.612(6) A 1
C C17B -0.0436(12) 0.3207(6) 0.35536(18) 0.082(2) Uani d 0.612(6) A 1
H H17A -0.068729 0.259543 0.341642 0.098 Uiso calc 0.612(6) A 1
H H17B -0.097603 0.303747 0.375127 0.098 Uiso calc 0.612(6) A 1
C C18 0.091(2) 0.3083(10) 0.3490(3) 0.066(3) Uani d 0.388(6) A 2
H H18 -0.011064 0.261066 0.356444 0.079 Uiso calc 0.388(6) A 2
C C19 0.1496(19) 0.3913(11) 0.3738(3) 0.088(3) Uani d 0.388(6) A 2
H H19A 0.284235 0.389665 0.376746 0.105 Uiso calc 0.388(6) A 2
H H19B 0.089260 0.373878 0.393055 0.105 Uiso calc 0.388(6) A 2
C C20 0.086(3) 0.5074(13) 0.3621(4) 0.104(5) Uani d 0.388(6) A 2
H H20A 0.024612 0.548628 0.378297 0.124 Uiso calc 0.388(6) A 2
H H20B 0.192226 0.549728 0.354836 0.124 Uiso calc 0.388(6) A 2
C C21 -0.051(3) 0.4833(14) 0.3361(4) 0.099(4) Uani d 0.388(6) A 2
H H21A -0.176717 0.472374 0.343864 0.119 Uiso calc 0.388(6) A 2
H H21B -0.052004 0.543380 0.321460 0.119 Uiso calc 0.388(6) A 2
C C22 0.0237(19) 0.3790(8) 0.3220(2) 0.076(3) Uani d 0.388(6) A 2
H H22A 0.126688 0.395255 0.308252 0.092 Uiso calc 0.388(6) A 2
H H22B -0.073782 0.341045 0.310661 0.092 Uiso calc 0.388(6) A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2543 0.3332 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1A P1A O2A . . 113.05(13) ?
O1A P1A O3A . . 110.42(13) ?
O1A P1A O4A . . 106.40(14) ?
O2A P1A O3A . . 110.45(13) ?
O2A P1A O4A . . 107.69(16) ?
O3A P1A O4A . . 108.61(17) ?
P1A O3A H3AA . . 116(3) ?
P1A O4A H4A . . 109.5 ?
O1B P1B O4B . . 109.16(13) ?
O2B P1B O1B . . 110.98(12) ?
O2B P1B O4B . . 108.57(13) ?
O3B P1B O1B . . 112.26(13) ?
O3B P1B O2B . . 111.55(14) ?
O3B P1B O4B . . 104.02(12) ?
P1B O2B H2BA . . 122(3) ?
P1B O4B H4B . . 109.5 ?
C1A N1A H1A . . 125.8 ?
C4A N1A H1A . . 125.8 ?
C4A N1A C1A . . 108.3(2) ?
N1A C1A H1AA . . 124.9 ?
C2A C1A N1A . . 110.3(3) ?
C2A C1A H1AA . . 124.9 ?
C5A N2A C4A . . 112.7(2) ?
C1A C2A H2A . . 126.8 ?
C1A C2A C3A . . 106.3(3) ?
C3A C2A H2A . . 126.8 ?
C5A N3A H3A . . 119.0 ?
C5A N3A C6A . . 122.1(2) ?
C6A N3A H3A . . 119.0 ?
C4A C3A C2A . . 106.4(2) ?
C6A C3A C2A . . 136.9(3) ?
C6A C3A C4A . . 116.6(2) ?
C8A N4A N5A . . 104.6(3) ?
N1A C4A C3A . . 108.6(2) ?
N2A C4A N1A . . 124.9(3) ?
N2A C4A C3A . . 126.5(2) ?
N4A N5A C10A . . 119.7(2) ?
C9A N5A N4A . . 112.6(2) ?
C9A N5A C10A . . 127.7(3) ?
N2A C5A N3A . . 125.8(3) ?
N2A C5A H5A . . 117.1 ?
N3A C5A H5A . . 117.1 ?
N3A C6A C3A . . 116.3(2) ?
N3A C6A C7A . . 118.6(2) ?
C3A C6A C7A . . 125.1(2) ?
C8A C7A C6A . . 127.8(3) ?
C9A C7A C6A . . 128.0(3) ?
C9A C7A C8A . . 104.1(2) ?
N4A C8A C7A . . 111.4(3) ?
N4A C8A H8A . . 124.3 ?
C7A C8A H8A . . 124.3 ?
N5A C9A C7A . . 107.3(3) ?
N5A C9A H9A . . 126.3 ?
C7A C9A H9A . . 126.3 ?
N5A C10A H10C . . 107.1 ?
N5A C10A C11A . . 106.1(3) ?
N5A C10A C13A . . 114.5(3) ?
C11A C10A H10C . . 107.1 ?
C13A C10A H10C . . 107.1 ?
C13A C10A C11A . . 114.6(3) ?
C10A C11A H11C . . 109.0 ?
C10A C11A H11D . . 109.0 ?
H11C C11A H11D . . 107.8 ?
C12A C11A C10A . . 113.1(3) ?
C12A C11A H11C . . 109.0 ?
C12A C11A H11D . . 109.0 ?
N6A C12A C11A . . 178.6(5) ?
C10A C13A H13A . . 106.5 ?
C10A C13A C17A . . 114.0(3) ?
C14A C13A C10A . . 118.4(4) ?
C14A C13A H13A . . 106.5 ?
C14A C13A C17A . . 104.1(4) ?
C17A C13A H13A . . 106.5 ?
C13A C14A H14C . . 110.7 ?
C13A C14A H14D . . 110.7 ?
C13A C14A C15A . . 105.0(4) ?
H14C C14A H14D . . 108.8 ?
C15A C14A H14C . . 110.7 ?
C15A C14A H14D . . 110.7 ?
C14A C15A H15C . . 110.2 ?
C14A C15A H15D . . 110.2 ?
H15C C15A H15D . . 108.5 ?
C16A C15A C14A . . 107.7(4) ?
C16A C15A H15C . . 110.2 ?
C16A C15A H15D . . 110.2 ?
C15A C16A H16C . . 110.3 ?
C15A C16A H16D . . 110.3 ?
C15A C16A C17A . . 106.9(5) ?
H16C C16A H16D . . 108.6 ?
C17A C16A H16C . . 110.3 ?
C17A C16A H16D . . 110.3 ?
C13A C17A H17C . . 111.0 ?
C13A C17A H17D . . 111.0 ?
C16A C17A C13A . . 103.7(4) ?
C16A C17A H17C . . 111.0 ?
C16A C17A H17D . . 111.0 ?
H17C C17A H17D . . 109.0 ?
C1B N1B H1B . . 125.6 ?
C4B N1B H1B . . 125.6 ?
C4B N1B C1B . . 108.8(3) ?
N1B C1B H1BA . . 124.7 ?
C2B C1B N1B . . 110.6(3) ?
C2B C1B H1BA . . 124.7 ?
C5B N2B C4B . . 113.5(3) ?
C1B C2B H2B . . 126.7 ?
C1B C2B C3B . . 106.6(3) ?
C3B C2B H2B . . 126.7 ?
C5B N3B H3B . . 118.2 ?
C5B N3B C6B . . 123.6(2) ?
C6B N3B H3B . . 118.2 ?
C4B C3B C2B . . 105.7(3) ?
C6B C3B C2B . . 137.6(3) ?
C6B C3B C4B . . 116.7(3) ?
C8B N4B N5B . . 104.9(3) ?
N1B C4B C3B . . 108.3(3) ?
N2B C4B N1B . . 125.0(3) ?
N2B C4B C3B . . 126.7(3) ?
N4B N5B C10B . . 120.8(3) ?
C9B N5B N4B . . 111.5(3) ?
C9B N5B C10B . . 127.4(3) ?
N2B C5B N3B . . 124.3(3) ?
N2B C5B H5B . . 117.8 ?
N3B C5B H5B . . 117.8 ?
N3B C6B C3B . . 115.1(2) ?
N3B C6B C7B . . 117.9(2) ?
C3B C6B C7B . . 127.0(3) ?
C8B C7B C6B . . 130.0(3) ?
C9B C7B C6B . . 127.3(3) ?
C9B C7B C8B . . 102.7(3) ?
N4B C8B C7B . . 112.4(3) ?
N4B C8B H8B . . 123.8 ?
C7B C8B H8B . . 123.8 ?
N5B C9B C7B . . 108.6(3) ?
N5B C9B H9B . . 125.7 ?
C7B C9B H9B . . 125.7 ?
N5B C10B H10A . . 102.4 ?
N5B C10B H10B . . 110.5 ?
N5B C10B C11B . . 109.3(3) ?
N5B C10B C13B . . 113.0(4) ?
N5B C10B C18 . . 107.0(6) ?
C11B C10B H10A . . 102.4 ?
C11B C10B H10B . . 110.5 ?
C11B C10B C13B . . 102.8(5) ?
C11B C10B C18 . . 129.9(7) ?
C13B C10B H10B . . 110.5 ?
C18 C10B H10A . . 102.4 ?
C10B C11B H11A . . 109.1 ?
C10B C11B H11B . . 109.1 ?
H11A C11B H11B . . 107.8 ?
C12B C11B C10B . . 112.6(4) ?
C12B C11B H11A . . 109.1 ?
C12B C11B H11B . . 109.1 ?
N6B C12B C11B . . 179.2(7) ?
C10B C13B H13B . . 109.4 ?
C14B C13B C10B . . 116.9(6) ?
C14B C13B H13B . . 109.4 ?
C14B C13B C17B . . 105.5(6) ?
C17B C13B C10B . . 106.0(7) ?
C17B C13B H13B . . 109.4 ?
C13B C14B H14A . . 111.0 ?
C13B C14B H14B . . 111.0 ?
H14A C14B H14B . . 109.0 ?
C15B C14B C13B . . 103.6(7) ?
C15B C14B H14A . . 111.0 ?
C15B C14B H14B . . 111.0 ?
C14B C15B H15A . . 111.1 ?
C14B C15B H15B . . 111.1 ?
H15A C15B H15B . . 109.1 ?
C16B C15B C14B . . 103.2(8) ?
C16B C15B H15A . . 111.1 ?
C16B C15B H15B . . 111.1 ?
C15B C16B H16A . . 110.7 ?
C15B C16B H16B . . 110.7 ?
H16A C16B H16B . . 108.8 ?
C17B C16B C15B . . 105.0(8) ?
C17B C16B H16A . . 110.7 ?
C17B C16B H16B . . 110.7 ?
C13B C17B H17A . . 110.3 ?
C13B C17B H17B . . 110.3 ?
C16B C17B C13B . . 107.0(7) ?
C16B C17B H17A . . 110.3 ?
C16B C17B H17B . . 110.3 ?
H17A C17B H17B . . 108.6 ?
C10B C18 H18 . . 110.4 ?
C10B C18 C19 . . 105.8(10) ?
C10B C18 C22 . . 114.1(9) ?
C19 C18 H18 . . 110.4 ?
C22 C18 H18 . . 110.4 ?
C22 C18 C19 . . 105.5(9) ?
C18 C19 H19A . . 110.5 ?
C18 C19 H19B . . 110.5 ?
C18 C19 C20 . . 106.0(10) ?
H19A C19 H19B . . 108.7 ?
C20 C19 H19A . . 110.5 ?
C20 C19 H19B . . 110.5 ?
C19 C20 H20A . . 110.7 ?
C19 C20 H20B . . 110.7 ?
H20A C20 H20B . . 108.8 ?
C21 C20 C19 . . 105.0(12) ?
C21 C20 H20A . . 110.7 ?
C21 C20 H20B . . 110.7 ?
C20 C21 H21A . . 111.0 ?
C20 C21 H21B . . 111.0 ?
H21A C21 H21B . . 109.0 ?
C22 C21 C20 . . 104.0(12) ?
C22 C21 H21A . . 111.0 ?
C22 C21 H21B . . 111.0 ?
C18 C22 H22A . . 110.8 ?
C18 C22 H22B . . 110.8 ?
C21 C22 C18 . . 105.0(10) ?
C21 C22 H22A . . 110.8 ?
C21 C22 H22B . . 110.8 ?
H22A C22 H22B . . 108.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1A O1A . 1.498(2) ?
P1A O2A . 1.522(2) ?
P1A O3A . 1.535(2) ?
P1A O4A . 1.543(2) ?
O3A H3AA . 0.825(14) ?
O4A H4A . 0.8200 ?
P1B O1B . 1.523(2) ?
P1B O2B . 1.520(2) ?
P1B O3B . 1.504(2) ?
P1B O4B . 1.559(2) ?
O2B H2BA . 0.829(14) ?
O4B H4B . 0.8200 ?
N1A H1A . 0.8600 ?
N1A C1A . 1.381(4) ?
N1A C4A . 1.348(3) ?
C1A H1AA . 0.9300 ?
C1A C2A . 1.354(4) ?
N2A C4A . 1.347(3) ?
N2A C5A . 1.320(4) ?
C2A H2A . 0.9300 ?
C2A C3A . 1.434(4) ?
N3A H3A . 0.8600 ?
N3A C5A . 1.345(4) ?
N3A C6A . 1.358(3) ?
C3A C4A . 1.407(4) ?
C3A C6A . 1.399(4) ?
N4A N5A . 1.360(4) ?
N4A C8A . 1.333(4) ?
N5A C9A . 1.336(4) ?
N5A C10A . 1.468(4) ?
C5A H5A . 0.9300 ?
N6A C12A . 1.118(5) ?
C6A C7A . 1.443(4) ?
C7A C8A . 1.417(4) ?
C7A C9A . 1.384(4) ?
C8A H8A . 0.9300 ?
C9A H9A . 0.9300 ?
C10A H10C . 0.9800 ?
C10A C11A . 1.527(5) ?
C10A C13A . 1.517(5) ?
C11A H11C . 0.9700 ?
C11A H11D . 0.9700 ?
C11A C12A . 1.455(5) ?
C13A H13A . 0.9800 ?
C13A C14A . 1.511(6) ?
C13A C17A . 1.528(6) ?
C14A H14C . 0.9700 ?
C14A H14D . 0.9700 ?
C14A C15A . 1.531(7) ?
C15A H15C . 0.9700 ?
C15A H15D . 0.9700 ?
C15A C16A . 1.477(9) ?
C16A H16C . 0.9700 ?
C16A H16D . 0.9700 ?
C16A C17A . 1.521(7) ?
C17A H17C . 0.9700 ?
C17A H17D . 0.9700 ?
N1B H1B . 0.8600 ?
N1B C1B . 1.362(4) ?
N1B C4B . 1.345(4) ?
C1B H1BA . 0.9300 ?
C1B C2B . 1.355(5) ?
N2B C4B . 1.336(4) ?
N2B C5B . 1.309(4) ?
C2B H2B . 0.9300 ?
C2B C3B . 1.427(4) ?
N3B H3B . 0.8600 ?
N3B C5B . 1.361(4) ?
N3B C6B . 1.364(3) ?
C3B C4B . 1.425(4) ?
C3B C6B . 1.393(4) ?
N4B N5B . 1.358(4) ?
N4B C8B . 1.308(5) ?
N5B C9B . 1.320(4) ?
N5B C10B . 1.475(4) ?
C5B H5B . 0.9300 ?
N6B C12B . 1.124(6) ?
C6B C7B . 1.444(4) ?
C7B C8B . 1.410(4) ?
C7B C9B . 1.380(4) ?
C8B H8B . 0.9300 ?
C9B H9B . 0.9300 ?
C10B H10A . 0.9800 ?
C10B H10B . 0.9800 ?
C10B C11B . 1.519(8) ?
C10B C13B . 1.564(8) ?
C10B C18 . 1.533(12) ?
C11B H11A . 0.9700 ?
C11B H11B . 0.9700 ?
C11B C12B . 1.457(6) ?
C13B H13B . 0.9800 ?
C13B C14B . 1.540(9) ?
C13B C17B . 1.549(11) ?
C14B H14A . 0.9700 ?
C14B H14B . 0.9700 ?
C14B C15B . 1.539(14) ?
C15B H15A . 0.9700 ?
C15B H15B . 0.9700 ?
C15B C16B . 1.531(15) ?
C16B H16A . 0.9700 ?
C16B H16B . 0.9700 ?
C16B C17B . 1.519(11) ?
C17B H17A . 0.9700 ?
C17B H17B . 0.9700 ?
C18 H18 . 0.9800 ?
C18 C19 . 1.538(15) ?
C18 C22 . 1.538(13) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C19 C20 . 1.561(18) ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
C20 C21 . 1.528(18) ?
C21 H21A . 0.9700 ?
C21 H21B . 0.9700 ?
C21 C22 . 1.503(17) ?
C22 H22A . 0.9700 ?
C22 H22B . 0.9700 ?
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
_geom_hbond_publ_flag
O3A H3AA O1B . 0.825(14) 1.704(15) 2.525(3) 173(4) yes
O4A H4A O3B 1_655 0.82 1.71 2.519(3) 170.9 yes
O2B H2BA O2A . 0.829(14) 1.672(19) 2.473(3) 162(4) yes
O4B H4B O3B 4_556 0.82 1.81 2.575(3) 154.2 yes
N1A H1A O2B 4_566 0.86 1.99 2.819(3) 160.6 yes
N3A H3A O1A . 0.86 1.73 2.578(3) 169.9 yes
N1B H1B N2A 4_456 0.86 2.35 3.120(4) 149.4 yes
N3B H3B O1B . 0.86 1.89 2.729(3) 165.2 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1A C1A C2A C3A . . . . 0.4(4) ?
C1A N1A C4A N2A . . . . -177.1(3) ?
C1A N1A C4A C3A . . . . 1.4(4) ?
C1A C2A C3A C4A . . . . 0.4(4) ?
C1A C2A C3A C6A . . . . 176.4(3) ?
C2A C3A C4A N1A . . . . -1.1(3) ?
C2A C3A C4A N2A . . . . 177.4(3) ?
C2A C3A C6A N3A . . . . -175.1(3) ?
C2A C3A C6A C7A . . . . 4.2(6) ?
N3A C6A C7A C8A . . . . 22.2(5) ?
N3A C6A C7A C9A . . . . -160.8(3) ?
C3A C6A C7A C8A . . . . -157.2(3) ?
C3A C6A C7A C9A . . . . 19.9(5) ?
N4A N5A C9A C7A . . . . 1.0(4) ?
N4A N5A C10A C11A . . . . 57.3(4) ?
N4A N5A C10A C13A . . . . -70.1(4) ?
C4A N1A C1A C2A . . . . -1.1(4) ?
C4A N2A C5A N3A . . . . -0.3(5) ?
C4A C3A C6A N3A . . . . 0.6(4) ?
C4A C3A C6A C7A . . . . 180.0(3) ?
N5A N4A C8A C7A . . . . 2.0(4) ?
N5A C10A C11A C12A . . . . -178.0(3) ?
N5A C10A C13A C14A . . . . 70.9(4) ?
N5A C10A C13A C17A . . . . -52.0(5) ?
C5A N2A C4A N1A . . . . 177.6(3) ?
C5A N2A C4A C3A . . . . -0.6(4) ?
C5A N3A C6A C3A . . . . -1.4(4) ?
C5A N3A C6A C7A . . . . 179.2(3) ?
C6A N3A C5A N2A . . . . 1.3(5) ?
C6A C3A C4A N1A . . . . -178.1(3) ?
C6A C3A C4A N2A . . . . 0.4(5) ?
C6A C7A C8A N4A . . . . 176.2(3) ?
C6A C7A C9A N5A . . . . -177.4(3) ?
C8A N4A N5A C9A . . . . -1.9(4) ?
C8A N4A N5A C10A . . . . 178.6(3) ?
C8A C7A C9A N5A . . . . 0.2(4) ?
C9A N5A C10A C11A . . . . -122.2(4) ?
C9A N5A C10A C13A . . . . 110.4(4) ?
C9A C7A C8A N4A . . . . -1.4(4) ?
C10A N5A C9A C7A . . . . -179.5(3) ?
C10A C13A C14A C15A . . . . -158.0(4) ?
C10A C13A C17A C16A . . . . 166.1(4) ?
C11A C10A C13A C14A . . . . -52.0(5) ?
C11A C10A C13A C17A . . . . -174.9(4) ?
C13A C10A C11A C12A . . . . -50.7(5) ?
C13A C14A C15A C16A . . . . 13.4(7) ?
C14A C13A C17A C16A . . . . 35.7(5) ?
C14A C15A C16A C17A . . . . 9.1(7) ?
C15A C16A C17A C13A . . . . -27.7(6) ?
C17A C13A C14A C15A . . . . -30.3(5) ?
N1B C1B C2B C3B . . . . 1.2(4) ?
C1B N1B C4B N2B . . . . 179.8(3) ?
C1B N1B C4B C3B . . . . -0.4(4) ?
C1B C2B C3B C4B . . . . -1.4(4) ?
C1B C2B C3B C6B . . . . -178.9(4) ?
C2B C3B C4B N1B . . . . 1.1(4) ?
C2B C3B C4B N2B . . . . -179.1(3) ?
C2B C3B C6B N3B . . . . 176.7(3) ?
C2B C3B C6B C7B . . . . -4.3(6) ?
N3B C6B C7B C8B . . . . 174.6(3) ?
N3B C6B C7B C9B . . . . -5.8(5) ?
C3B C6B C7B C8B . . . . -4.4(5) ?
C3B C6B C7B C9B . . . . 175.2(3) ?
N4B N5B C9B C7B . . . . -0.1(4) ?
N4B N5B C10B C11B . . . . -101.8(4) ?
N4B N5B C10B C13B . . . . 144.5(5) ?
N4B N5B C10B C18 . . . . 113.4(6) ?
C4B N1B C1B C2B . . . . -0.5(4) ?
C4B N2B C5B N3B . . . . -1.8(5) ?
C4B C3B C6B N3B . . . . -0.6(4) ?
C4B C3B C6B C7B . . . . 178.5(3) ?
N5B N4B C8B C7B . . . . -0.7(5) ?
N5B C10B C11B C12B . . . . 62.2(5) ?
N5B C10B C13B C14B . . . . 171.1(6) ?
N5B C10B C13B C17B . . . . -71.8(6) ?
N5B C10B C18 C19 . . . . 98.4(9) ?
N5B C10B C18 C22 . . . . -146.1(9) ?
C5B N2B C4B N1B . . . . -178.1(3) ?
C5B N2B C4B C3B . . . . 2.1(5) ?
C5B N3B C6B C3B . . . . 0.9(4) ?
C5B N3B C6B C7B . . . . -178.2(3) ?
C6B N3B C5B N2B . . . . 0.3(5) ?
C6B C3B C4B N1B . . . . 179.2(3) ?
C6B C3B C4B N2B . . . . -1.0(5) ?
C6B C7B C8B N4B . . . . -179.7(3) ?
C6B C7B C9B N5B . . . . -180.0(3) ?
C8B N4B N5B C9B . . . . 0.5(5) ?
C8B N4B N5B C10B . . . . 175.1(4) ?
C8B C7B C9B N5B . . . . -0.3(4) ?
C9B N5B C10B C11B . . . . 71.9(5) ?
C9B N5B C10B C13B . . . . -41.9(7) ?
C9B N5B C10B C18 . . . . -72.9(8) ?
C9B C7B C8B N4B . . . . 0.6(4) ?
C10B N5B C9B C7B . . . . -174.3(4) ?
C10B C13B C14B C15B . . . . 144.7(9) ?
C10B C13B C17B C16B . . . . -129.5(6) ?
C10B C18 C19 C20 . . . . 129.7(12) ?
C10B C18 C22 C21 . . . . -145.0(13) ?
C11B C10B C13B C14B . . . . 53.5(8) ?
C11B C10B C13B C17B . . . . 170.6(5) ?
C11B C10B C18 C19 . . . . -36.5(11) ?
C11B C10B C18 C22 . . . . 79.0(12) ?
C13B C10B C11B C12B . . . . -177.6(4) ?
C13B C14B C15B C16B . . . . -39.3(11) ?
C14B C13B C17B C16B . . . . -5.0(9) ?
C14B C15B C16B C17B . . . . 36.4(11) ?
C15B C16B C17B C13B . . . . -19.5(11) ?
C17B C13B C14B C15B . . . . 27.2(10) ?
C18 C10B C11B C12B . . . . -163.6(7) ?
C18 C19 C20 C21 . . . . 14.9(19) ?
C19 C18 C22 C21 . . . . -29.3(15) ?
C19 C20 C21 C22 . . . . -33(2) ?
C20 C21 C22 C18 . . . . 38.8(19) ?
C22 C18 C19 C20 . . . . 8.5(15) ?

_cod_database_fobs_code 2023211
