#------------------------------------------------------------------------------
#$Date: 2022-02-15 01:37:52 +0200 (Tue, 15 Feb 2022) $
#$Revision: 272954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/44/7244413.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_7244413
loop_
_publ_author_name
'Boycov, Denis'
'Manin, Alex N.'
'Drozd, Ksenia V.'
'Andrei, Churakov'
'Perlovich, German L.'
_publ_section_title
;
 Thermal Methods Usage Features for Multicomponent Crystals Screening
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D1CE01717A
_journal_year                    2022
_chemical_formula_moiety         'C16 H17 F N3 O3, C8 H12 N O, C H4 O'
_chemical_formula_sum            'C25 H33 F N4 O5'
_chemical_formula_weight         488.55
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-12-22 deposited with the CCDC.	2022-02-14 downloaded from the CCDC.
;
_cell_angle_alpha                105.309(4)
_cell_angle_beta                 107.316(4)
_cell_angle_gamma                101.130(4)
_cell_formula_units_Z            2
_cell_length_a                   8.4159(11)
_cell_length_b                   12.6978(17)
_cell_length_c                   13.8293(17)
_cell_measurement_reflns_used    2941
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.368
_cell_measurement_theta_min      2.555
_cell_volume                     1300.3(3)
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2016)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9474
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.555
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       prism
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.350
_exptl_transmission_factor_max   0.8622
_exptl_transmission_factor_min   0.7022
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         5013
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0660
_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)+(0.0904P)²+0.0555P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1656
_refine_ls_wR_factor_ref         0.1846
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3182
_reflns_number_total             5013
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ce01717a2.cif
_cod_data_source_block           a
_cod_database_code               7244413
_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_min   0.964
_shelx_estimated_absorpt_t_max   0.968
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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
F1 F 0.0734(2) 1.22799(13) 0.50074(13) 0.0596(5) Uani 1 1 d . . . . .
O1 O 0.3770(3) 1.08004(15) 0.77384(14) 0.0515(5) Uani 1 1 d . . . . .
O2 O 0.4843(3) 0.76268(16) 0.74749(16) 0.0593(6) Uani 1 1 d . . . . .
O3 O 0.5314(3) 0.93278(16) 0.86307(15) 0.0531(5) Uani 1 1 d . . . . .
N1 N 0.3296(3) 0.85933(17) 0.48395(16) 0.0401(5) Uani 1 1 d . . . . .
N2 N 0.0602(3) 1.09738(18) 0.30184(17) 0.0452(6) Uani 1 1 d . . . . .
N3 N -0.0703(3) 1.1497(2) 0.10703(18) 0.0495(6) Uani 1 1 d . . . . .
C1 C 0.3596(3) 1.0084(2) 0.6876(2) 0.0369(6) Uani 1 1 d . . . . .
C2 C 0.4093(3) 0.9042(2) 0.6766(2) 0.0380(6) Uani 1 1 d . . . . .
C3 C 0.3909(3) 0.8370(2) 0.5760(2) 0.0405(6) Uani 1 1 d . . . . .
C4 C 0.4796(3) 0.8644(2) 0.7692(2) 0.0401(6) Uani 1 1 d . . . . .
C5 C 0.3148(4) 0.7763(3) 0.3818(2) 0.0484(7) Uani 1 1 d . . . . .
C6 C 0.1354(6) 0.6942(4) 0.3202(3) 0.0772(11) Uani 1 1 d . . . . .
C8 C 0.2840(3) 1.0275(2) 0.58628(19) 0.0366(6) Uani 1 1 d . . . . .
C9 C 0.2192(4) 1.1221(2) 0.5880(2) 0.0406(6) Uani 1 1 d . . . . .
C10 C 0.1474(4) 1.1410(2) 0.4953(2) 0.0418(6) Uani 1 1 d . . . . .
C11 C 0.1394(3) 1.0736(2) 0.3940(2) 0.0393(6) Uani 1 1 d . . . . .
C12 C 0.2023(4) 0.9806(2) 0.3920(2) 0.0408(6) Uani 1 1 d . . . . .
C13 C 0.2710(3) 0.9552(2) 0.4863(2) 0.0369(6) Uani 1 1 d . . . . .
C14 C 0.1216(4) 1.2139(2) 0.3007(2) 0.0486(7) Uani 1 1 d . . . . .
C15 C -0.0174(5) 1.2343(3) 0.2144(2) 0.0512(8) Uani 1 1 d . . . . .
C16 C 0.0177(4) 1.0106(3) 0.1957(2) 0.0484(7) Uani 1 1 d . . . . .
C17 C -0.1183(4) 1.0339(3) 0.1111(2) 0.0471(7) Uani 1 1 d . . . . .
H3 H 0.418(3) 0.771(2) 0.569(2) 0.041(7) Uiso 1 1 d . . . . .
H9 H 0.223(3) 1.174(2) 0.656(2) 0.041(7) Uiso 1 1 d . . . . .
H12 H 0.195(3) 0.9371(18) 0.3267(19) 0.021(6) Uiso 1 1 d . . . . .
H31 H 0.026(4) 1.161(2) 0.085(2) 0.058(9) Uiso 1 1 d . . . . .
H51 H 0.393(4) 0.732(2) 0.399(2) 0.059(9) Uiso 1 1 d . . . . .
H52 H 0.343(4) 0.815(2) 0.335(2) 0.052(8) Uiso 1 1 d . . . . .
H61 H 0.135(5) 0.635(3) 0.256(3) 0.092(12) Uiso 1 1 d . . . . .
H62 H 0.100(5) 0.646(3) 0.361(3) 0.091(13) Uiso 1 1 d . . . . .
H63 H 0.041(5) 0.734(3) 0.309(3) 0.095(13) Uiso 1 1 d . . . . .
H141 H 0.228(4) 1.216(2) 0.284(2) 0.061(9) Uiso 1 1 d . . . . .
H142 H 0.148(3) 1.269(2) 0.379(2) 0.050(7) Uiso 1 1 d . . . . .
H151 H 0.028(4) 1.308(3) 0.215(3) 0.079(11) Uiso 1 1 d . . . . .
H152 H -0.131(4) 1.233(2) 0.236(2) 0.054(8) Uiso 1 1 d . . . . .
H161 H -0.044(4) 0.932(3) 0.194(2) 0.060(9) Uiso 1 1 d . . . . .
H162 H 0.125(4) 1.005(2) 0.174(2) 0.045(7) Uiso 1 1 d . . . . .
H171 H -0.227(4) 1.028(2) 0.128(2) 0.059(9) Uiso 1 1 d . . . . .
H172 H -0.136(4) 0.979(2) 0.044(2) 0.051(8) Uiso 1 1 d . . . . .
O21 O 0.7175(3) 0.75242(15) 0.91680(18) 0.0526(5) Uani 1 1 d . . . . .
N21 N 0.5880(4) 0.15697(18) 0.9944(2) 0.0409(6) Uani 1 1 d . . . . .
C21 C 0.7119(4) 0.6450(2) 0.9177(2) 0.0436(7) Uani 1 1 d . . . . .
C22 C 0.8139(4) 0.6319(3) 1.0100(3) 0.0557(8) Uani 1 1 d . . . . .
C23 C 0.8116(4) 0.5250(3) 1.0151(3) 0.0552(8) Uani 1 1 d . . . . .
C24 C 0.7095(4) 0.4273(2) 0.9286(2) 0.0447(7) Uani 1 1 d . . . . .
C25 C 0.6069(5) 0.4415(3) 0.8380(3) 0.0575(8) Uani 1 1 d . . . . .
C26 C 0.6071(5) 0.5481(3) 0.8312(3) 0.0570(8) Uani 1 1 d . . . . .
C27 C 0.7077(5) 0.3098(3) 0.9348(3) 0.0531(8) Uani 1 1 d . . . . .
C28 C 0.5899(4) 0.2730(2) 0.9916(2) 0.0426(7) Uani 1 1 d . . . . .
H21 H 0.620(6) 0.743(3) 0.844(3) 0.111(14) Uiso 1 1 d . . . . .
H22 H 0.873(4) 0.700(3) 1.073(3) 0.078(10) Uiso 1 1 d . . . . .
H23 H 0.888(4) 0.520(3) 1.078(3) 0.065(9) Uiso 1 1 d . . . . .
H25 H 0.534(4) 0.383(3) 0.782(3) 0.073(11) Uiso 1 1 d . . . . .
H26 H 0.538(5) 0.554(3) 0.773(3) 0.094(13) Uiso 1 1 d . . . . .
H27 H 0.705(4) 0.150(2) 1.025(2) 0.053(8) Uiso 1 1 d . . . . .
H28 H 0.529(4) 0.136(3) 1.038(3) 0.065(9) Uiso 1 1 d . . . . .
H29 H 0.543(4) 0.103(3) 0.921(3) 0.077(10) Uiso 1 1 d . . . . .
H271 H 0.667(4) 0.247(3) 0.867(3) 0.066(10) Uiso 1 1 d . . . . .
H272 H 0.819(4) 0.310(2) 0.972(2) 0.051(8) Uiso 1 1 d . . . . .
H281 H 0.461(4) 0.272(2) 0.952(2) 0.053(8) Uiso 1 1 d . . . . .
H282 H 0.624(3) 0.325(2) 1.066(2) 0.044(7) Uiso 1 1 d . . . . .
O18 O 0.2901(10) 0.5636(6) 0.5811(6) 0.145(3) Uiso 0.579(6) 1 d D . P A -1
H18 H 0.350283 0.625601 0.632953 0.217 Uiso 0.579(6) 1 d R U P A -1
C18 C 0.1323(17) 0.5297(14) 0.5905(13) 0.246(8) Uiso 0.579(6) 1 d D . P A -1
H18A H 0.146178 0.498936 0.647872 0.370 Uiso 0.579(6) 1 calc R U P A -1
H18B H 0.051486 0.472216 0.524084 0.370 Uiso 0.579(6) 1 calc R U P A -1
H18C H 0.088749 0.594190 0.606151 0.370 Uiso 0.579(6) 1 calc R U P A -1
O19 O 0.4955(18) 0.5691(10) 0.4651(10) 0.189(5) Uiso 0.421(6) 1 d D . P A -2
H19 H 0.560251 0.528392 0.450722 0.284 Uiso 0.421(6) 1 d R U P A -2
C19 C 0.409(3) 0.5309(19) 0.5245(16) 0.211(9) Uiso 0.421(6) 1 d D . P A -2
H19A H 0.405635 0.452730 0.515461 0.317 Uiso 0.421(6) 1 calc R U P A -2
H19B H 0.292511 0.536121 0.500581 0.317 Uiso 0.421(6) 1 calc R U P A -2
H19C H 0.468806 0.576918 0.599303 0.317 Uiso 0.421(6) 1 calc R U P 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 0.0033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C13 119.6(2) . . ?
C3 N1 C5 118.6(2) . . ?
C13 N1 C5 121.7(2) . . ?
C11 N2 C16 118.3(2) . . ?
C11 N2 C14 118.4(2) . . ?
C16 N2 C14 111.2(2) . . ?
C15 N3 C17 110.0(2) . . ?
C15 N3 H31 107.4(18) . . ?
C17 N3 H31 110.2(18) . . ?
O1 C1 C2 125.7(2) . . ?
O1 C1 C8 119.4(2) . . ?
C2 C1 C8 114.9(2) . . ?
C3 C2 C1 118.6(2) . . ?
C3 C2 C4 117.6(2) . . ?
C1 C2 C4 123.8(2) . . ?
N1 C3 C2 125.6(2) . . ?
N1 C3 H3 116.0(16) . . ?
C2 C3 H3 118.3(16) . . ?
O3 C4 O2 123.2(2) . . ?
O3 C4 C2 119.1(2) . . ?
O2 C4 C2 117.7(2) . . ?
N1 C5 C6 113.0(3) . . ?
N1 C5 H51 107.6(17) . . ?
C6 C5 H51 107.3(18) . . ?
N1 C5 H52 111.0(16) . . ?
C6 C5 H52 107.1(17) . . ?
H51 C5 H52 111(2) . . ?
C5 C6 H61 110(2) . . ?
C5 C6 H62 112(2) . . ?
H61 C6 H62 101(3) . . ?
C5 C6 H63 113(2) . . ?
H61 C6 H63 118(3) . . ?
H62 C6 H63 101(3) . . ?
C13 C8 C9 117.9(2) . . ?
C13 C8 C1 123.1(2) . . ?
C9 C8 C1 119.0(2) . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 119.5(14) . . ?
C8 C9 H9 120.4(14) . . ?
C9 C10 F1 117.4(2) . . ?
C9 C10 C11 123.7(2) . . ?
F1 C10 C11 118.9(2) . . ?
C12 C11 N2 123.4(2) . . ?
C12 C11 C10 116.3(2) . . ?
N2 C11 C10 120.1(2) . . ?
C11 C12 C13 121.6(2) . . ?
C11 C12 H12 115.9(14) . . ?
C13 C12 H12 122.4(14) . . ?
N1 C13 C8 118.0(2) . . ?
N1 C13 C12 121.7(2) . . ?
C8 C13 C12 120.3(2) . . ?
N2 C14 C15 109.6(2) . . ?
N2 C14 H141 105.1(17) . . ?
C15 C14 H141 111.3(18) . . ?
N2 C14 H142 105.8(14) . . ?
C15 C14 H142 112.8(15) . . ?
H141 C14 H142 112(2) . . ?
N3 C15 C14 113.4(2) . . ?
N3 C15 H151 111(2) . . ?
C14 C15 H151 107(2) . . ?
N3 C15 H152 108.5(15) . . ?
C14 C15 H152 109.2(15) . . ?
H151 C15 H152 108(3) . . ?
N2 C16 C17 109.1(2) . . ?
N2 C16 H161 110.0(16) . . ?
C17 C16 H161 103.2(17) . . ?
N2 C16 H162 114.5(15) . . ?
C17 C16 H162 110.5(14) . . ?
H161 C16 H162 109(2) . . ?
N3 C17 C16 114.5(2) . . ?
N3 C17 H171 104.2(16) . . ?
C16 C17 H171 109.4(17) . . ?
N3 C17 H172 110.4(16) . . ?
C16 C17 H172 105.5(17) . . ?
H171 C17 H172 113(2) . . ?
C21 O21 H21 106(2) . . ?
C28 N21 H27 113.0(16) . . ?
C28 N21 H28 112.5(18) . . ?
H27 N21 H28 104(2) . . ?
C28 N21 H29 109.4(19) . . ?
H27 N21 H29 103(3) . . ?
H28 N21 H29 114(3) . . ?
O21 C21 C26 123.1(3) . . ?
O21 C21 C22 118.7(3) . . ?
C26 C21 C22 118.2(3) . . ?
C23 C22 C21 120.8(3) . . ?
C23 C22 H22 122(2) . . ?
C21 C22 H22 117(2) . . ?
C22 C23 C24 121.6(3) . . ?
C22 C23 H23 118.2(19) . . ?
C24 C23 H23 120.0(19) . . ?
C25 C24 C23 117.0(3) . . ?
C25 C24 C27 121.7(3) . . ?
C23 C24 C27 121.3(3) . . ?
C24 C25 C26 122.4(3) . . ?
C24 C25 H25 121(2) . . ?
C26 C25 H25 116(2) . . ?
C21 C26 C25 120.0(3) . . ?
C21 C26 H26 120(2) . . ?
C25 C26 H26 120(3) . . ?
C28 C27 C24 111.5(2) . . ?
C28 C27 H271 104.3(19) . . ?
C24 C27 H271 116.8(19) . . ?
C28 C27 H272 108.5(18) . . ?
C24 C27 H272 110.0(18) . . ?
H271 C27 H272 105(2) . . ?
N21 C28 C27 110.3(2) . . ?
N21 C28 H281 108.5(15) . . ?
C27 C28 H281 110.9(15) . . ?
N21 C28 H282 108.0(15) . . ?
C27 C28 H282 113.5(15) . . ?
H281 C28 H282 105(2) . . ?
C18 O18 H18 107.8 . . ?
O18 C18 H18A 109.5 . . ?
O18 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O18 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C19 O19 H19 111.2 . . ?
O19 C19 H19A 109.5 . . ?
O19 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O19 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
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C10 1.364(3) . ?
O1 C1 1.242(3) . ?
O2 C4 1.258(3) . ?
O3 C4 1.245(3) . ?
N1 C3 1.350(3) . ?
N1 C13 1.396(3) . ?
N1 C5 1.477(3) . ?
N2 C11 1.391(3) . ?
N2 C16 1.475(3) . ?
N2 C14 1.476(3) . ?
N3 C15 1.462(4) . ?
N3 C17 1.469(4) . ?
N3 H31 0.95(3) . ?
C1 C2 1.446(3) . ?
C1 C8 1.461(3) . ?
C2 C3 1.372(4) . ?
C2 C4 1.501(3) . ?
C3 H3 0.90(3) . ?
C5 C6 1.500(5) . ?
C5 H51 0.96(3) . ?
C5 H52 0.96(3) . ?
C6 H61 1.00(4) . ?
C6 H62 0.99(4) . ?
C6 H63 1.02(4) . ?
C8 C13 1.403(3) . ?
C8 C9 1.410(3) . ?
C9 C10 1.351(4) . ?
C9 H9 0.98(3) . ?
C10 C11 1.411(3) . ?
C11 C12 1.380(4) . ?
C12 C13 1.408(4) . ?
C12 H12 0.90(2) . ?
C14 C15 1.520(4) . ?
C14 H141 0.99(3) . ?
C14 H142 1.05(3) . ?
C15 H151 0.94(3) . ?
C15 H152 1.08(3) . ?
C16 C17 1.511(4) . ?
C16 H161 1.02(3) . ?
C16 H162 1.05(3) . ?
C17 H171 1.01(3) . ?
C17 H172 0.95(3) . ?
O21 C21 1.359(3) . ?
O21 H21 1.05(5) . ?
N21 C28 1.481(3) . ?
N21 H27 0.98(3) . ?
N21 H28 0.95(3) . ?
N21 H29 0.97(4) . ?
C21 C26 1.378(4) . ?
C21 C22 1.382(4) . ?
C22 C23 1.373(4) . ?
C22 H22 0.97(3) . ?
C23 C24 1.379(4) . ?
C23 H23 0.94(3) . ?
C24 C25 1.373(4) . ?
C24 C27 1.515(4) . ?
C25 C26 1.381(4) . ?
C25 H25 0.87(3) . ?
C26 H26 0.87(4) . ?
C27 C28 1.514(4) . ?
C27 H271 0.97(3) . ?
C27 H272 0.93(3) . ?
C28 H281 1.05(3) . ?
C28 H282 0.98(3) . ?
O18 C18 1.370(9) . ?
O18 H18 0.8500 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
O19 C19 1.367(9) . ?
O19 H19 0.8500 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
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
N3 H31 O21 0.95(3) 2.23(3) 3.137(3) 158(2) 2_676
O21 H21 O2 1.05(5) 1.59(5) 2.622(3) 165(3) .
N21 H27 N3 0.98(3) 1.89(3) 2.866(4) 171(2) 1_646
N21 H28 O3 0.95(3) 1.94(3) 2.849(3) 161(3) 2_667
N21 H29 O1 0.97(4) 2.01(4) 2.818(3) 140(3) 1_545
N21 H29 O3 0.97(4) 2.07(3) 2.804(3) 131(3) 1_545
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -176.2(3) . . . . ?
C8 C1 C2 C3 3.4(4) . . . . ?
O1 C1 C2 C4 4.1(4) . . . . ?
C8 C1 C2 C4 -176.3(2) . . . . ?
C13 N1 C3 C2 -3.1(4) . . . . ?
C5 N1 C3 C2 -178.7(3) . . . . ?
C1 C2 C3 N1 0.1(4) . . . . ?
C4 C2 C3 N1 179.8(2) . . . . ?
C3 C2 C4 O3 165.4(3) . . . . ?
C1 C2 C4 O3 -14.9(4) . . . . ?
C3 C2 C4 O2 -14.1(4) . . . . ?
C1 C2 C4 O2 165.6(2) . . . . ?
C3 N1 C5 C6 96.2(4) . . . . ?
C13 N1 C5 C6 -79.3(4) . . . . ?
O1 C1 C8 C13 175.3(2) . . . . ?
C2 C1 C8 C13 -4.3(4) . . . . ?
O1 C1 C8 C9 -5.2(4) . . . . ?
C2 C1 C8 C9 175.2(2) . . . . ?
C13 C8 C9 C10 0.0(4) . . . . ?
C1 C8 C9 C10 -179.4(2) . . . . ?
C8 C9 C10 F1 174.4(2) . . . . ?
C8 C9 C10 C11 -3.2(4) . . . . ?
C16 N2 C11 C12 9.4(4) . . . . ?
C14 N2 C11 C12 -129.9(3) . . . . ?
C16 N2 C11 C10 -165.9(3) . . . . ?
C14 N2 C11 C10 54.8(4) . . . . ?
C9 C10 C11 C12 3.2(4) . . . . ?
F1 C10 C11 C12 -174.3(2) . . . . ?
C9 C10 C11 N2 178.8(2) . . . . ?
F1 C10 C11 N2 1.3(4) . . . . ?
N2 C11 C12 C13 -175.7(2) . . . . ?
C10 C11 C12 C13 -0.2(4) . . . . ?
C3 N1 C13 C8 2.2(4) . . . . ?
C5 N1 C13 C8 177.6(2) . . . . ?
C3 N1 C13 C12 -178.5(2) . . . . ?
C5 N1 C13 C12 -3.1(4) . . . . ?
C9 C8 C13 N1 -177.9(2) . . . . ?
C1 C8 C13 N1 1.6(4) . . . . ?
C9 C8 C13 C12 2.8(4) . . . . ?
C1 C8 C13 C12 -177.7(2) . . . . ?
C11 C12 C13 N1 178.0(2) . . . . ?
C11 C12 C13 C8 -2.7(4) . . . . ?
C11 N2 C14 C15 -159.9(2) . . . . ?
C16 N2 C14 C15 58.1(3) . . . . ?
C17 N3 C15 C14 52.1(4) . . . . ?
N2 C14 C15 N3 -55.8(4) . . . . ?
C11 N2 C16 C17 160.6(2) . . . . ?
C14 N2 C16 C17 -57.4(3) . . . . ?
C15 N3 C17 C16 -52.3(4) . . . . ?
N2 C16 C17 N3 55.2(4) . . . . ?
O21 C21 C22 C23 179.5(3) . . . . ?
C26 C21 C22 C23 0.4(5) . . . . ?
C21 C22 C23 C24 0.6(5) . . . . ?
C22 C23 C24 C25 -1.5(5) . . . . ?
C22 C23 C24 C27 -180.0(3) . . . . ?
C23 C24 C25 C26 1.5(5) . . . . ?
C27 C24 C25 C26 180.0(3) . . . . ?
O21 C21 C26 C25 -179.5(3) . . . . ?
C22 C21 C26 C25 -0.4(5) . . . . ?
C24 C25 C26 C21 -0.6(5) . . . . ?
C25 C24 C27 C28 -97.5(4) . . . . ?
C23 C24 C27 C28 80.9(4) . . . . ?
C24 C27 C28 N21 178.8(3) . . . . ?
