#------------------------------------------------------------------------------
#$Date: 2021-06-05 21:11:38 +0300 (Sat, 05 Jun 2021) $
#$Revision: 265961 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/25/7242581.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_7242581
loop_
_publ_author_name
'Yu, Kaxi'
'Chen, Shuai'
'Amgoth, Chander'
'Tang, Guping'
'Bai, Hongzhen'
'Hu, Xiurong'
_publ_section_title
;
 Two polymorphs of remdesivir: crystal structure, solubility, and
 pharmacokinetic study
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              2923
_journal_page_last               2927
_journal_paper_doi               10.1039/D1CE00175B
_journal_volume                  23
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C27 H35 N6 O8 P'
_chemical_formula_sum            'C27 H35 N6 O8 P'
_chemical_formula_weight         602.58
_chemical_name_common            remdesivir
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-09-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-09-07 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;
_cell_angle_alpha                96.105(4)
_cell_angle_beta                 99.219(4)
_cell_angle_gamma                94.937(4)
_cell_formula_units_Z            2
_cell_length_a                   8.5565(11)
_cell_length_b                   10.5456(16)
_cell_length_c                   17.147(2)
_cell_measurement_reflns_used    783
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      40.07
_cell_measurement_theta_min      7.47
_cell_volume                     1510.2(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      170.02
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.1329
_diffrn_reflns_av_unetI/netI     0.2058
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24237
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.319
_diffrn_reflns_theta_min         4.097
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.837
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5372
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       prism
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.005
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details
;
 Flack x determined using 1145 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.18(5)
_refine_ls_extinction_coef       0.020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     770
_refine_ls_number_reflns         11093
_refine_ls_number_restraints     552
_refine_ls_restrained_S_all      0.986
_refine_ls_R_factor_all          0.2598
_refine_ls_R_factor_gt           0.1215
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2953
_refine_ls_wR_factor_ref         0.3938
_reflns_Friedel_coverage         0.943
_reflns_Friedel_fraction_full    0.944
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                4142
_reflns_number_total             11093
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce00175b2.cif
_cod_data_source_block           rdvformi
_cod_depositor_comments
'Adding full bibliography for 7242581--7242582.cif.'
_cod_original_cell_volume        1510.1(4)
_cod_database_code               7242581
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.959
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C23A-C22A = C26A-C23A = C26A-C27A
 1.53 with sigma of 0.02
 C23A-C24A
 1.53 with sigma of 0.02
 C24A-C25A
 1.53 with sigma of 0.02
 C24B-C23B = C24B-C25B
 1.53 with sigma of 0.02
 C26B-C23B
 1.53 with sigma of 0.02
 C26B-C27B
 1.53 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
O8B \\sim C22B \\sim C23B \\sim C24B \\sim C25B \\sim C27B: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02
O8A \\sim C22A \\sim C23A \\sim C24A \\sim C25A \\sim C26A \\sim C27A: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02
C22B \\sim C23B \\sim C26B \\sim C27B: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
4.a Riding coordinates:
 N6A(H6A), N6B(H6B)
4.b Rotating group:
 N1A(H1AA,H1AB), N1B(H1BA,H1BB)
4.c Ternary CH refined with riding coordinates:
 C8A(H8A), C9A(H9A), C10A(H10A), C19A(H19A), C23A(H23A), C8B(H8B), C9B(H9B),
 C10B(H10B), C19B(H19B), C23B(H23B)
4.d Secondary CH2 refined with riding coordinates:
 C12A(H12A,H12B), C22A(H22A,H22B), C24A(H24A,H24B), C26A(H26A,H26B), C12B(H12C,
 H12D), C22B(H22C,H22D), C24B(H24C,H24D), C26B(H26C,H26D)
4.e Aromatic/amide H refined with riding coordinates:
 C5A(H5A), C4A(H4A), C2A(H2AA), C14A(H14A), C15A(H15A), C16A(H16A), C17A(H17A),
  C18A(H18A), C5B(H5B), C4B(H4B), C2B(H2BA), C14B(H14B), C15B(H15B), C16B(H16B),
  C17B(H17B), C18B(H18B)
4.f Idealised Me refined as rotating group:
 C20A(H20A,H20B,H20C), C25A(H25A,H25B,H25C), C27A(H27A,H27B,H27C), C20B(H20D,
 H20E,H20F), C25B(H25D,H25E,H25F), C27B(H27D,H27E,H27F)
4.g Idealised tetrahedral OH refined as rotating group:
 O3A(H3A), O2A(H2A), O3B(H3B), O2B(H2B)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1A P 1.2781(7) 0.6226(5) 0.7044(3) 0.0896(18) Uani 1 1 d . U . . .
O1A O 1.6237(15) 0.2917(10) 0.6610(7) 0.074(3) Uani 1 1 d . U . . .
O3A O 1.7312(15) 0.4404(11) 0.4962(7) 0.078(4) Uani 1 1 d . U . . .
H3A H 1.688770 0.404427 0.450755 0.117 Uiso 1 1 calc GR . . . .
O2A O 1.7962(15) 0.5670(11) 0.6460(7) 0.077(3) Uani 1 1 d . U . . .
H2A H 1.804890 0.629018 0.619494 0.115 Uiso 1 1 calc GR . . . .
O4A O 1.404(2) 0.5321(17) 0.7363(11) 0.125(6) Uani 1 1 d . U . . .
O6A O 1.3818(18) 0.7462(16) 0.7522(9) 0.106(5) Uani 1 1 d . U . . .
O5A O 1.240(2) 0.6212(15) 0.6203(9) 0.108(5) Uani 1 1 d . U . . .
O7A O 1.201(3) 0.396(3) 0.8737(15) 0.174(9) Uani 1 1 d . U . . .
O8A O 0.947(2) 0.4061(14) 0.8267(10) 0.109(4) Uani 1 1 d . U . . .
N6A N 1.1170(19) 0.6011(17) 0.7432(11) 0.094(5) Uani 1 1 d . U . . .
H6A H 1.052401 0.658033 0.728494 0.113 Uiso 1 1 d R . . . .
N4A N 1.7029(18) 0.0423(13) 0.5722(9) 0.072(4) Uani 1 1 d . U . . .
N3A N 1.786(2) 0.0381(13) 0.6469(9) 0.081(4) Uani 1 1 d . U . . .
N2A N 1.775(2) -0.1911(14) 0.6024(10) 0.077(4) Uani 1 1 d . U . . .
N1A N 1.660(2) -0.2818(15) 0.4777(10) 0.084(5) Uani 1 1 d . U . . .
H1AA H 1.680156 -0.352122 0.499793 0.101 Uiso 1 1 d GR . . . .
H1AB H 1.556818 -0.288671 0.457222 0.101 Uiso 1 1 d GR . . . .
N5A N 2.009(3) 0.3114(16) 0.6373(10) 0.090(5) Uani 1 1 d . U . . .
C8A C 1.599(2) 0.4201(16) 0.6859(12) 0.079(5) Uani 1 1 d . U . . .
H8A H 1.665446 0.450758 0.739078 0.094 Uiso 1 1 calc R . . . .
C9A C 1.642(2) 0.5032(17) 0.6247(11) 0.071(5) Uani 1 1 d . U . . .
H9A H 1.561147 0.563805 0.611362 0.085 Uiso 1 1 calc R . . . .
C10A C 1.641(2) 0.3976(15) 0.5546(10) 0.062(4) Uani 1 1 d . U . . .
H10A H 1.528346 0.372613 0.527908 0.075 Uiso 1 1 calc R . . . .
C7A C 1.701(2) 0.2845(18) 0.5940(11) 0.073(5) Uani 1 1 d . U . . .
C6A C 1.657(2) 0.1566(16) 0.5444(12) 0.071(5) Uani 1 1 d . U . . .
C5A C 1.572(2) 0.1179(15) 0.4679(11) 0.069(5) Uani 1 1 d . U . . .
H5A H 1.523754 0.173574 0.433321 0.083 Uiso 1 1 calc R . . . .
C4A C 1.568(2) -0.0080(18) 0.4505(11) 0.077(5) Uani 1 1 d . U . . .
H4A H 1.514812 -0.056532 0.402178 0.093 Uiso 1 1 calc R . . . .
C3A C 1.652(2) -0.0570(13) 0.5134(10) 0.060(4) Uani 1 1 d . U . . .
C1A C 1.698(2) -0.1802(18) 0.5319(14) 0.075(5) Uani 1 1 d . U . . .
C2A C 1.818(3) -0.083(2) 0.6547(13) 0.094(6) Uani 1 1 d . U . . .
H2AA H 1.878669 -0.094977 0.704296 0.113 Uiso 1 1 calc R . . . .
C11A C 1.873(3) 0.3043(16) 0.6217(12) 0.071(5) Uani 1 1 d . U . . .
C12A C 1.418(3) 0.414(2) 0.6924(17) 0.116(8) Uani 1 1 d . U . . .
H12A H 1.351168 0.404324 0.639020 0.140 Uiso 1 1 calc R . . . .
H12B H 1.386962 0.340962 0.720694 0.140 Uiso 1 1 calc R . . . .
C13A C 1.337(3) 0.868(2) 0.7453(16) 0.098(6) Uani 1 1 d . U . . .
C14A C 1.278(3) 0.929(3) 0.810(2) 0.124(8) Uani 1 1 d . U . . .
H14A H 1.262239 0.882716 0.852706 0.149 Uiso 1 1 calc R . . . .
C15A C 1.241(4) 1.053(4) 0.812(3) 0.164(11) Uani 1 1 d . U . . .
H15A H 1.202503 1.091824 0.856944 0.197 Uiso 1 1 calc R . . . .
C16A C 1.258(4) 1.119(4) 0.752(3) 0.166(12) Uani 1 1 d . U . . .
H16A H 1.229828 1.204361 0.751896 0.199 Uiso 1 1 calc R . . . .
C17A C 1.325(4) 1.054(3) 0.682(3) 0.158(12) Uani 1 1 d . U . . .
H17A H 1.341397 1.100022 0.638579 0.189 Uiso 1 1 calc R . . . .
C18A C 1.360(3) 0.930(3) 0.6819(17) 0.129(9) Uani 1 1 d . U . . .
H18A H 1.400144 0.887855 0.638459 0.155 Uiso 1 1 calc R . . . .
C19A C 1.116(3) 0.589(2) 0.8261(13) 0.096(6) Uani 1 1 d . U . . .
H19A H 1.222188 0.628620 0.855683 0.115 Uiso 1 1 calc R . . . .
C20A C 0.988(3) 0.673(3) 0.8569(16) 0.114(8) Uani 1 1 d . U . . .
H20A H 1.029620 0.764272 0.863956 0.172 Uiso 1 1 calc GR . . . .
H20B H 0.967048 0.648425 0.907951 0.172 Uiso 1 1 calc GR . . . .
H20C H 0.889514 0.659661 0.817929 0.172 Uiso 1 1 calc GR . . . .
C21A C 1.096(4) 0.456(3) 0.8466(17) 0.115(7) Uani 1 1 d . U . . .
C22A C 0.914(3) 0.273(2) 0.8382(19) 0.128(6) Uani 1 1 d D U . . .
H22A H 1.009454 0.242855 0.868344 0.154 Uiso 1 1 calc R . . . .
H22B H 0.886523 0.219175 0.785888 0.154 Uiso 1 1 calc R . . . .
C23A C 0.779(4) 0.258(3) 0.883(2) 0.163(7) Uani 1 1 d D U . . .
H23A H 0.684283 0.276277 0.844780 0.196 Uiso 1 1 calc R . . . .
C24A C 0.749(5) 0.115(3) 0.889(3) 0.186(9) Uani 1 1 d D U . . .
H24A H 0.780521 0.114894 0.947272 0.223 Uiso 1 1 calc R . . . .
H24B H 0.631236 0.103723 0.880214 0.223 Uiso 1 1 calc R . . . .
C25A C 0.781(6) -0.019(4) 0.860(3) 0.240(15) Uani 1 1 d D U . . .
H25A H 0.767716 -0.029424 0.802064 0.360 Uiso 1 1 calc GR . . . .
H25B H 0.706889 -0.081224 0.877534 0.360 Uiso 1 1 calc GR . . . .
H25C H 0.890796 -0.031804 0.882563 0.360 Uiso 1 1 calc GR . . . .
C26A C 0.773(4) 0.342(3) 0.958(2) 0.179(8) Uani 1 1 d D U . . .
H26A H 0.812755 0.430900 0.952800 0.215 Uiso 1 1 calc R . . . .
H26B H 0.844475 0.312572 1.002479 0.215 Uiso 1 1 calc R . . . .
C27A C 0.604(4) 0.338(3) 0.976(2) 0.154(10) Uani 1 1 d D U . . .
H27A H 0.544703 0.396881 0.945592 0.231 Uiso 1 1 calc GR . . . .
H27B H 0.607854 0.363159 1.033190 0.231 Uiso 1 1 calc GR . . . .
H27C H 0.550385 0.250409 0.961509 0.231 Uiso 1 1 calc GR . . . .
P1B P 0.5675(6) 0.3610(4) 0.2575(3) 0.0749(15) Uani 1 1 d . U . . .
O1B O 1.0067(14) 0.7034(9) 0.3022(7) 0.071(3) Uani 1 1 d . U . . .
O3B O 1.2094(15) 0.5550(11) 0.4602(8) 0.080(4) Uani 1 1 d . U . . .
H3B H 1.202630 0.580101 0.507560 0.120 Uiso 1 1 calc GR . . . .
O2B O 1.1507(15) 0.4326(11) 0.3099(7) 0.071(3) Uani 1 1 d . U . . .
H2B H 1.164666 0.365841 0.331706 0.107 Uiso 1 1 calc GR . . . .
O4B O 0.7110(14) 0.4317(11) 0.2260(7) 0.073(3) Uani 1 1 d . U . . .
O6B O 0.5563(15) 0.2253(11) 0.2063(8) 0.079(3) Uani 1 1 d . U . . .
O5B O 0.5929(17) 0.3605(12) 0.3428(7) 0.086(4) Uani 1 1 d . U . . .
O7B O 0.177(2) 0.587(2) 0.1122(14) 0.149(7) Uani 1 1 d . U . . .
O8B O 0.438(3) 0.6256(16) 0.1331(11) 0.125(5) Uani 1 1 d . U . . .
N6B N 0.4055(17) 0.4128(14) 0.2229(8) 0.070(4) Uani 1 1 d . U . . .
H6B H 0.400760 0.488673 0.248748 0.084 Uiso 1 1 d R . . . .
N4B N 1.1572(17) 0.9532(13) 0.3940(9) 0.067(4) Uani 1 1 d . U . . .
N3B N 1.2129(18) 0.9735(13) 0.3254(8) 0.069(4) Uani 1 1 d . U . . .
N2B N 1.2077(18) 1.1980(13) 0.3662(9) 0.070(4) Uani 1 1 d . U . . .
N1B N 1.153(2) 1.2801(15) 0.4878(10) 0.090(5) Uani 1 1 d . U . . .
H1BA H 1.158908 1.352569 0.465615 0.108 Uiso 1 1 d GR . . . .
H1BB H 1.060483 1.271761 0.505463 0.108 Uiso 1 1 d GR . . . .
N5B N 1.411(2) 0.7071(12) 0.3270(10) 0.073(4) Uani 1 1 d . U . . .
C8B C 0.948(2) 0.5694(15) 0.2734(10) 0.064(4) Uani 1 1 d . U . . .
H8B H 0.982870 0.543633 0.221460 0.077 Uiso 1 1 calc R . . . .
C9B C 1.0221(19) 0.4906(16) 0.3367(11) 0.065(4) Uani 1 1 d . U . . .
H9B H 0.941194 0.424861 0.349032 0.078 Uiso 1 1 calc R . . . .
C10B C 1.080(2) 0.5937(14) 0.4084(11) 0.062(4) Uani 1 1 d . U . . .
H10B H 0.991171 0.611605 0.437775 0.074 Uiso 1 1 calc R . . . .
C7B C 1.127(2) 0.7124(14) 0.3647(12) 0.068(5) Uani 1 1 d . U . . .
C6B C 1.122(2) 0.8369(15) 0.4192(11) 0.066(4) Uani 1 1 d . U . . .
C5B C 1.075(2) 0.8592(17) 0.4894(13) 0.080(5) Uani 1 1 d . U . . .
H5B H 1.043164 0.794879 0.520283 0.095 Uiso 1 1 calc R . . . .
C4B C 1.078(2) 0.9929(18) 0.5112(13) 0.084(5) Uani 1 1 d . U . . .
H4B H 1.048587 1.034342 0.557692 0.100 Uiso 1 1 calc R . . . .
C3B C 1.135(2) 1.0513(18) 0.4509(10) 0.067(5) Uani 1 1 d . U . . .
C1B C 1.161(2) 1.1759(16) 0.4327(12) 0.066(5) Uani 1 1 d . U . . .
C2B C 1.228(2) 1.0939(19) 0.3155(12) 0.078(5) Uani 1 1 d . U . . .
H2BA H 1.258224 1.112254 0.266546 0.094 Uiso 1 1 calc R . . . .
C11B C 1.285(3) 0.7104(14) 0.3418(11) 0.067(5) Uani 1 1 d . U . . .
C12B C 0.770(2) 0.5621(15) 0.2623(11) 0.072(5) Uani 1 1 d . U . . .
H12C H 0.735126 0.580201 0.314236 0.086 Uiso 1 1 calc R . . . .
H12D H 0.730508 0.625193 0.227229 0.086 Uiso 1 1 calc R . . . .
C13B C 0.677(3) 0.1427(19) 0.2107(13) 0.087(6) Uani 1 1 d . U . . .
C14B C 0.678(3) 0.059(2) 0.2651(17) 0.115(8) Uani 1 1 d . U . . .
H14B H 0.608638 0.062340 0.303023 0.138 Uiso 1 1 calc R . . . .
C15B C 0.786(4) -0.035(3) 0.2639(19) 0.119(8) Uani 1 1 d . U . . .
H15B H 0.789119 -0.095286 0.301248 0.143 Uiso 1 1 calc R . . . .
C16B C 0.883(3) -0.039(2) 0.2114(18) 0.105(7) Uani 1 1 d . U . . .
H16B H 0.953511 -0.104471 0.209960 0.126 Uiso 1 1 calc R . . . .
C17B C 0.883(3) 0.054(3) 0.1563(18) 0.117(8) Uani 1 1 d . U . . .
H17B H 0.952399 0.051931 0.118315 0.141 Uiso 1 1 calc R . . . .
C18B C 0.783(3) 0.145(2) 0.1591(16) 0.103(7) Uani 1 1 d . U . . .
H18B H 0.786495 0.210746 0.125365 0.124 Uiso 1 1 calc R . . . .
C19B C 0.344(2) 0.4184(19) 0.1407(13) 0.083(5) Uani 1 1 d . U . . .
H19B H 0.428689 0.393897 0.109520 0.100 Uiso 1 1 calc R . . . .
C20B C 0.196(3) 0.319(2) 0.1112(16) 0.126(9) Uani 1 1 d . U . . .
H20D H 0.228564 0.232337 0.111308 0.189 Uiso 1 1 calc GR . . . .
H20E H 0.148649 0.331869 0.057086 0.189 Uiso 1 1 calc GR . . . .
H20F H 0.118240 0.331008 0.146729 0.189 Uiso 1 1 calc GR . . . .
C21B C 0.310(3) 0.550(3) 0.1253(14) 0.098(6) Uani 1 1 d . U . . .
C22B C 0.423(4) 0.765(3) 0.1275(19) 0.145(7) Uani 1 1 d . U . . .
H22C H 0.514559 0.818556 0.161735 0.174 Uiso 1 1 calc R . . . .
H22D H 0.323473 0.789709 0.143989 0.174 Uiso 1 1 calc R . . . .
C23B C 0.423(5) 0.780(3) 0.038(2) 0.168(7) Uani 1 1 d D U . . .
H23B H 0.319215 0.738534 0.006653 0.202 Uiso 1 1 calc R . . . .
C24B C 0.432(5) 0.922(3) 0.032(3) 0.194(9) Uani 1 1 d D U . . .
H24C H 0.444145 0.939026 -0.022747 0.233 Uiso 1 1 calc R . . . .
H24D H 0.524541 0.968316 0.069581 0.233 Uiso 1 1 calc R . . . .
C25B C 0.277(6) 0.968(4) 0.052(3) 0.216(13) Uani 1 1 d D U . . .
H25D H 0.189666 0.936989 0.008153 0.324 Uiso 1 1 calc GR . . . .
H25E H 0.287407 1.061721 0.060816 0.324 Uiso 1 1 calc GR . . . .
H25F H 0.254600 0.933739 0.100714 0.324 Uiso 1 1 calc GR . . . .
C26B C 0.560(5) 0.727(4) -0.001(3) 0.193(9) Uani 1 1 d D U . . .
H26C H 0.528730 0.634468 -0.018641 0.232 Uiso 1 1 calc R . . . .
H26D H 0.564712 0.768954 -0.049701 0.232 Uiso 1 1 calc R . . . .
C27B C 0.727(6) 0.739(5) 0.045(3) 0.256(16) Uani 1 1 d D U . . .
H27D H 0.803096 0.762294 0.010174 0.384 Uiso 1 1 calc GR . . . .
H27E H 0.749673 0.657521 0.064376 0.384 Uiso 1 1 calc GR . . . .
H27F H 0.738465 0.806344 0.090300 0.384 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2596 0.3354 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4A P1A O6A 92.2(10) . . ?
O4A P1A N6A 110.8(10) . . ?
O6A P1A N6A 107.7(9) . . ?
O5A P1A O4A 117.1(10) . . ?
O5A P1A O6A 116.5(9) . . ?
O5A P1A N6A 110.9(11) . . ?
C7A O1A C8A 111.3(12) . . ?
C10A O3A H3A 109.5 . . ?
C9A O2A H2A 109.5 . . ?
C12A O4A P1A 121.2(18) . . ?
C13A O6A P1A 122.0(14) . . ?
C21A O8A C22A 117(2) . . ?
P1A N6A H6A 109.2 . . ?
C19A N6A P1A 124.5(15) . . ?
C19A N6A H6A 108.5 . . ?
N3A N4A C6A 123.1(15) . . ?
C3A N4A N3A 128.1(13) . . ?
C3A N4A C6A 108.8(14) . . ?
C2A N3A N4A 109.1(15) . . ?
C1A N2A C2A 118.0(15) . . ?
H1AA N1A H1AB 108.6 . . ?
C1A N1A H1AA 109.7 . . ?
C1A N1A H1AB 110.6 . . ?
O1A C8A H8A 110.2 . . ?
O1A C8A C9A 108.5(15) . . ?
O1A C8A C12A 104.6(15) . . ?
C9A C8A H8A 110.2 . . ?
C9A C8A C12A 113.0(16) . . ?
C12A C8A H8A 110.2 . . ?
O2A C9A C8A 112.8(15) . . ?
O2A C9A H9A 111.8 . . ?
O2A C9A C10A 108.6(15) . . ?
C8A C9A H9A 111.8 . . ?
C8A C9A C10A 99.3(13) . . ?
C10A C9A H9A 111.8 . . ?
O3A C10A C9A 112.4(12) . . ?
O3A C10A H10A 108.3 . . ?
O3A C10A C7A 114.8(14) . . ?
C9A C10A H10A 108.3 . . ?
C7A C10A C9A 104.5(14) . . ?
C7A C10A H10A 108.3 . . ?
O1A C7A C10A 100.4(13) . . ?
O1A C7A C6A 110.6(14) . . ?
O1A C7A C11A 108.7(15) . . ?
C6A C7A C10A 114.8(15) . . ?
C11A C7A C10A 111.7(15) . . ?
C11A C7A C6A 110.2(15) . . ?
N4A C6A C7A 121.9(16) . . ?
C5A C6A N4A 104.5(15) . . ?
C5A C6A C7A 133.6(15) . . ?
C6A C5A H5A 125.0 . . ?
C4A C5A C6A 110.1(15) . . ?
C4A C5A H5A 125.0 . . ?
C5A C4A H4A 125.4 . . ?
C5A C4A C3A 109.1(16) . . ?
C3A C4A H4A 125.4 . . ?
N4A C3A C4A 107.4(13) . . ?
N4A C3A C1A 115.2(15) . . ?
C4A C3A C1A 137.4(17) . . ?
N2A C1A N1A 120.3(17) . . ?
N2A C1A C3A 119.8(17) . . ?
N1A C1A C3A 119.9(19) . . ?
N3A C2A N2A 129.7(19) . . ?
N3A C2A H2AA 115.1 . . ?
N2A C2A H2AA 115.1 . . ?
N5A C11A C7A 173(2) . . ?
O4A C12A C8A 103.8(19) . . ?
O4A C12A H12A 111.0 . . ?
O4A C12A H12B 111.0 . . ?
C8A C12A H12A 111.0 . . ?
C8A C12A H12B 111.0 . . ?
H12A C12A H12B 109.0 . . ?
O6A C13A C14A 117(2) . . ?
C18A C13A O6A 122(3) . . ?
C18A C13A C14A 121(3) . . ?
C13A C14A H14A 118.8 . . ?
C15A C14A C13A 122(3) . . ?
C15A C14A H14A 118.8 . . ?
C14A C15A H15A 120.0 . . ?
C16A C15A C14A 120(4) . . ?
C16A C15A H15A 120.0 . . ?
C15A C16A H16A 120.9 . . ?
C15A C16A C17A 118(4) . . ?
C17A C16A H16A 120.9 . . ?
C16A C17A H17A 120.1 . . ?
C18A C17A C16A 120(3) . . ?
C18A C17A H17A 120.1 . . ?
C13A C18A C17A 119(3) . . ?
C13A C18A H18A 120.7 . . ?
C17A C18A H18A 120.7 . . ?
N6A C19A H19A 106.4 . . ?
N6A C19A C20A 109.6(19) . . ?
N6A C19A C21A 116(2) . . ?
C20A C19A H19A 106.4 . . ?
C21A C19A H19A 106.4 . . ?
C21A C19A C20A 112(2) . . ?
C19A C20A H20A 109.5 . . ?
C19A C20A H20B 109.5 . . ?
C19A C20A H20C 109.5 . . ?
H20A C20A H20B 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
O7A C21A O8A 123(3) . . ?
O7A C21A C19A 126(3) . . ?
O8A C21A C19A 111(2) . . ?
O8A C22A H22A 109.6 . . ?
O8A C22A H22B 109.6 . . ?
O8A C22A C23A 110.1(19) . . ?
H22A C22A H22B 108.2 . . ?
C23A C22A H22A 109.6 . . ?
C23A C22A H22B 109.6 . . ?
C22A C23A H23A 104.4 . . ?
C22A C23A C24A 106(2) . . ?
C22A C23A C26A 122(3) . . ?
C24A C23A H23A 104.4 . . ?
C26A C23A H23A 104.4 . . ?
C26A C23A C24A 114(3) . . ?
C23A C24A H24A 100.2 . . ?
C23A C24A H24B 100.2 . . ?
H24A C24A H24B 104.2 . . ?
C25A C24A C23A 146(3) . . ?
C25A C24A H24A 100.2 . . ?
C25A C24A H24B 100.2 . . ?
C24A C25A H25A 109.5 . . ?
C24A C25A H25B 109.5 . . ?
C24A C25A H25C 109.5 . . ?
H25A C25A H25B 109.5 . . ?
H25A C25A H25C 109.5 . . ?
H25B C25A H25C 109.5 . . ?
C23A C26A H26A 109.4 . . ?
C23A C26A H26B 109.4 . . ?
C23A C26A C27A 111(3) . . ?
H26A C26A H26B 108.0 . . ?
C27A C26A H26A 109.4 . . ?
C27A C26A H26B 109.4 . . ?
C26A C27A H27A 109.5 . . ?
C26A C27A H27B 109.5 . . ?
C26A C27A H27C 109.5 . . ?
H27A C27A H27B 109.5 . . ?
H27A C27A H27C 109.5 . . ?
H27B C27A H27C 109.5 . . ?
O4B P1B O6B 99.2(7) . . ?
O4B P1B N6B 110.3(8) . . ?
O5B P1B O4B 113.9(8) . . ?
O5B P1B O6B 115.8(7) . . ?
O5B P1B N6B 113.8(8) . . ?
N6B P1B O6B 102.4(7) . . ?
C7B O1B C8B 111.2(11) . . ?
C10B O3B H3B 109.5 . . ?
C9B O2B H2B 109.5 . . ?
C12B O4B P1B 118.1(11) . . ?
C13B O6B P1B 125.0(12) . . ?
C21B O8B C22B 118(2) . . ?
P1B N6B H6B 108.7 . . ?
C19B N6B P1B 126.5(13) . . ?
C19B N6B H6B 107.3 . . ?
N3B N4B C6B 126.5(15) . . ?
N3B N4B C3B 123.9(13) . . ?
C6B N4B C3B 109.6(14) . . ?
C2B N3B N4B 112.6(15) . . ?
C1B N2B C2B 117.2(15) . . ?
H1BA N1B H1BB 108.4 . . ?
C1B N1B H1BA 110.5 . . ?
C1B N1B H1BB 109.9 . . ?
O1B C8B H8B 110.1 . . ?
O1B C8B C9B 106.1(13) . . ?
O1B C8B C12B 106.1(12) . . ?
C9B C8B H8B 110.1 . . ?
C12B C8B H8B 110.1 . . ?
C12B C8B C9B 114.0(13) . . ?
O2B C9B C8B 108.9(14) . . ?
O2B C9B H9B 111.3 . . ?
O2B C9B C10B 111.6(14) . . ?
C8B C9B H9B 111.3 . . ?
C8B C9B C10B 102.1(13) . . ?
C10B C9B H9B 111.3 . . ?
O3B C10B C9B 110.8(13) . . ?
O3B C10B H10B 110.3 . . ?
O3B C10B C7B 114.0(13) . . ?
C9B C10B H10B 110.3 . . ?
C9B C10B C7B 100.7(13) . . ?
C7B C10B H10B 110.3 . . ?
O1B C7B C10B 102.5(13) . . ?
O1B C7B C6B 108.3(13) . . ?
O1B C7B C11B 113.8(17) . . ?
C6B C7B C10B 109.1(14) . . ?
C11B C7B C10B 113.0(13) . . ?
C11B C7B C6B 109.8(14) . . ?
N4B C6B C7B 119.9(16) . . ?
C5B C6B N4B 107.6(15) . . ?
C5B C6B C7B 132.3(15) . . ?
C6B C5B H5B 125.0 . . ?
C6B C5B C4B 109.9(15) . . ?
C4B C5B H5B 125.0 . . ?
C5B C4B H4B 126.9 . . ?
C3B C4B C5B 106.1(17) . . ?
C3B C4B H4B 126.9 . . ?
C4B C3B N4B 106.7(15) . . ?
C4B C3B C1B 136.6(18) . . ?
C1B C3B N4B 116.5(15) . . ?
N2B C1B N1B 118.1(15) . . ?
N2B C1B C3B 120.9(17) . . ?
N1B C1B C3B 120.7(17) . . ?
N3B C2B N2B 128.6(17) . . ?
N3B C2B H2BA 115.7 . . ?
N2B C2B H2BA 115.7 . . ?
N5B C11B C7B 177(2) . . ?
O4B C12B C8B 106.3(13) . . ?
O4B C12B H12C 110.5 . . ?
O4B C12B H12D 110.5 . . ?
C8B C12B H12C 110.5 . . ?
C8B C12B H12D 110.5 . . ?
H12C C12B H12D 108.7 . . ?
C14B C13B O6B 118(2) . . ?
C14B C13B C18B 122(2) . . ?
C18B C13B O6B 120.3(19) . . ?
C13B C14B H14B 121.0 . . ?
C13B C14B C15B 118(3) . . ?
C15B C14B H14B 121.0 . . ?
C14B C15B H15B 119.6 . . ?
C16B C15B C14B 121(3) . . ?
C16B C15B H15B 119.6 . . ?
C15B C16B H16B 120.1 . . ?
C15B C16B C17B 120(2) . . ?
C17B C16B H16B 120.1 . . ?
C16B C17B H17B 120.3 . . ?
C18B C17B C16B 119(2) . . ?
C18B C17B H17B 120.3 . . ?
C13B C18B H18B 120.1 . . ?
C17B C18B C13B 120(2) . . ?
C17B C18B H18B 120.1 . . ?
N6B C19B H19B 107.3 . . ?
N6B C19B C20B 110.9(18) . . ?
N6B C19B C21B 111.8(18) . . ?
C20B C19B H19B 107.3 . . ?
C21B C19B H19B 107.3 . . ?
C21B C19B C20B 112(2) . . ?
C19B C20B H20D 109.5 . . ?
C19B C20B H20E 109.5 . . ?
C19B C20B H20F 109.5 . . ?
H20D C20B H20E 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
O7B C21B O8B 123(2) . . ?
O7B C21B C19B 125(2) . . ?
O8B C21B C19B 112(2) . . ?
O8B C22B H22C 110.8 . . ?
O8B C22B H22D 110.8 . . ?
O8B C22B C23B 105(2) . . ?
H22C C22B H22D 108.9 . . ?
C23B C22B H22C 110.8 . . ?
C23B C22B H22D 110.8 . . ?
C22B C23B H23B 108.4 . . ?
C22B C23B C26B 118(3) . . ?
C24B C23B C22B 107(3) . . ?
C24B C23B H23B 108.4 . . ?
C24B C23B C26B 107(3) . . ?
C26B C23B H23B 108.4 . . ?
C23B C24B H24C 110.4 . . ?
C23B C24B H24D 110.4 . . ?
C23B C24B C25B 107(3) . . ?
H24C C24B H24D 108.6 . . ?
C25B C24B H24C 110.4 . . ?
C25B C24B H24D 110.4 . . ?
C24B C25B H25D 109.5 . . ?
C24B C25B H25E 109.5 . . ?
C24B C25B H25F 109.5 . . ?
H25D C25B H25E 109.5 . . ?
H25D C25B H25F 109.5 . . ?
H25E C25B H25F 109.5 . . ?
C23B C26B H26C 107.2 . . ?
C23B C26B H26D 107.2 . . ?
H26C C26B H26D 106.8 . . ?
C27B C26B C23B 121(4) . . ?
C27B C26B H26C 107.2 . . ?
C27B C26B H26D 107.2 . . ?
C26B C27B H27D 109.5 . . ?
C26B C27B H27E 109.5 . . ?
C26B C27B H27F 109.5 . . ?
H27D C27B H27E 109.5 . . ?
H27D C27B H27F 109.5 . . ?
H27E C27B H27F 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1A O4A 1.574(16) . ?
P1A O6A 1.580(17) . ?
P1A O5A 1.424(15) . ?
P1A N6A 1.634(17) . ?
O1A C8A 1.42(2) . ?
O1A C7A 1.42(2) . ?
O3A H3A 0.8400 . ?
O3A C10A 1.443(19) . ?
O2A H2A 0.8400 . ?
O2A C9A 1.40(2) . ?
O4A C12A 1.41(3) . ?
O6A C13A 1.38(3) . ?
O7A C21A 1.21(3) . ?
O8A C21A 1.31(3) . ?
O8A C22A 1.45(3) . ?
N6A H6A 0.8803 . ?
N6A C19A 1.44(3) . ?
N4A N3A 1.37(2) . ?
N4A C6A 1.41(2) . ?
N4A C3A 1.36(2) . ?
N3A C2A 1.34(2) . ?
N2A C1A 1.30(2) . ?
N2A C2A 1.36(3) . ?
N1A H1AA 0.8862 . ?
N1A H1AB 0.8867 . ?
N1A C1A 1.32(2) . ?
N5A C11A 1.15(2) . ?
C8A H8A 1.0000 . ?
C8A C9A 1.51(2) . ?
C8A C12A 1.56(3) . ?
C9A H9A 1.0000 . ?
C9A C10A 1.55(2) . ?
C10A H10A 1.0000 . ?
C10A C7A 1.52(2) . ?
C7A C6A 1.50(3) . ?
C7A C11A 1.46(3) . ?
C6A C5A 1.39(2) . ?
C5A H5A 0.9500 . ?
C5A C4A 1.33(2) . ?
C4A H4A 0.9500 . ?
C4A C3A 1.37(2) . ?
C3A C1A 1.44(2) . ?
C2A H2AA 0.9500 . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C13A C14A 1.41(4) . ?
C13A C18A 1.36(3) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.37(4) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.33(5) . ?
C16A H16A 0.9500 . ?
C16A C17A 1.53(5) . ?
C17A H17A 0.9500 . ?
C17A C18A 1.37(4) . ?
C18A H18A 0.9500 . ?
C19A H19A 1.0000 . ?
C19A C20A 1.58(3) . ?
C19A C21A 1.49(3) . ?
C20A H20A 0.9800 . ?
C20A H20B 0.9800 . ?
C20A H20C 0.9800 . ?
C22A H22A 0.9900 . ?
C22A H22B 0.9900 . ?
C22A C23A 1.49(2) . ?
C23A H23A 1.0000 . ?
C23A C24A 1.53(2) . ?
C23A C26A 1.49(3) . ?
C24A H24A 0.9900 . ?
C24A H24B 0.9900 . ?
C24A C25A 1.50(3) . ?
C25A H25A 0.9800 . ?
C25A H25B 0.9800 . ?
C25A H25C 0.9800 . ?
C26A H26A 0.9900 . ?
C26A H26B 0.9900 . ?
C26A C27A 1.53(2) . ?
C27A H27A 0.9800 . ?
C27A H27B 0.9800 . ?
C27A H27C 0.9800 . ?
P1B O4B 1.579(12) . ?
P1B O6B 1.585(13) . ?
P1B O5B 1.444(13) . ?
P1B N6B 1.583(15) . ?
O1B C8B 1.463(19) . ?
O1B C7B 1.35(2) . ?
O3B H3B 0.8400 . ?
O3B C10B 1.42(2) . ?
O2B H2B 0.8400 . ?
O2B C9B 1.418(19) . ?
O4B C12B 1.461(19) . ?
O6B C13B 1.40(2) . ?
O7B C21B 1.23(3) . ?
O8B C21B 1.27(3) . ?
O8B C22B 1.50(3) . ?
N6B H6B 0.8800 . ?
N6B C19B 1.43(2) . ?
N4B N3B 1.367(19) . ?
N4B C6B 1.37(2) . ?
N4B C3B 1.39(2) . ?
N3B C2B 1.30(2) . ?
N2B C1B 1.30(2) . ?
N2B C2B 1.37(2) . ?
N1B H1BA 0.8905 . ?
N1B H1BB 0.8907 . ?
N1B C1B 1.39(2) . ?
N5B C11B 1.14(2) . ?
C8B H8B 1.0000 . ?
C8B C9B 1.53(2) . ?
C8B C12B 1.50(2) . ?
C9B H9B 1.0000 . ?
C9B C10B 1.54(2) . ?
C10B H10B 1.0000 . ?
C10B C7B 1.58(2) . ?
C7B C6B 1.54(2) . ?
C7B C11B 1.47(3) . ?
C6B C5B 1.33(2) . ?
C5B H5B 0.9500 . ?
C5B C4B 1.42(2) . ?
C4B H4B 0.9500 . ?
C4B C3B 1.39(2) . ?
C3B C1B 1.39(2) . ?
C2B H2BA 0.9500 . ?
C12B H12C 0.9900 . ?
C12B H12D 0.9900 . ?
C13B C14B 1.35(3) . ?
C13B C18B 1.37(3) . ?
C14B H14B 0.9500 . ?
C14B C15B 1.41(3) . ?
C15B H15B 0.9500 . ?
C15B C16B 1.32(4) . ?
C16B H16B 0.9500 . ?
C16B C17B 1.44(4) . ?
C17B H17B 0.9500 . ?
C17B C18B 1.33(3) . ?
C18B H18B 0.9500 . ?
C19B H19B 1.0000 . ?
C19B C20B 1.55(3) . ?
C19B C21B 1.49(3) . ?
C20B H20D 0.9800 . ?
C20B H20E 0.9800 . ?
C20B H20F 0.9800 . ?
C22B H22C 0.9900 . ?
C22B H22D 0.9900 . ?
C22B C23B 1.56(4) . ?
C23B H23B 1.0000 . ?
C23B C24B 1.51(3) . ?
C23B C26B 1.56(3) . ?
C24B H24C 0.9900 . ?
C24B H24D 0.9900 . ?
C24B C25B 1.53(3) . ?
C25B H25D 0.9800 . ?
C25B H25E 0.9800 . ?
C25B H25F 0.9800 . ?
C26B H26C 0.9900 . ?
C26B H26D 0.9900 . ?
C26B C27B 1.51(3) . ?
C27B H27D 0.9800 . ?
C27B H27E 0.9800 . ?
C27B H27F 0.9800 . ?
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
O3A H3A O5B 0.84 1.89 2.719(18) 167.5 1_655
O2A H2A N2A 0.84 1.98 2.746(17) 150.9 1_565
O3B H3B O5A 0.84 1.90 2.73(2) 165.2 .
O2B H2B N2B 0.84 1.97 2.803(17) 170.6 1_545
