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#$Date: 2023-04-05 10:00:23 +0300 (Wed, 05 Apr 2023) $
#$Revision: 282371 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/70/8107017.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_8107017
loop_
_publ_author_name
'Makhathini, Sifiso S.'
'Samipillai, Marivel'
'Govender, Thavendran'
'Naicker, Tricia'
_publ_section_title
;
 Crystal structure of
 2-ethyl-1-tert-butyl-2-((4-fluorophenyl)(tert-butoxycarbonylamino)methyl)-3-oxo-pyrrolidine-1,2-dicarboxylate,
 C24H33FN2O7
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              819
_journal_page_last               821
_journal_paper_doi               10.1515/ncrs-2015-0280
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety         'C24 H33 F N2 O7'
_chemical_formula_sum            'C24 H33 F N2 O7'
_chemical_formula_weight         480.52
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                112.2940(10)
_cell_angle_beta                 100.5570(10)
_cell_angle_gamma                105.775(2)
_cell_formula_units_Z            2
_cell_length_a                   11.0118(7)
_cell_length_b                   11.5684(7)
_cell_length_c                   11.7276(7)
_cell_measurement_reflns_used    8917
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      2.28
_cell_volume                     1259.57(14)
_computing_cell_refinement       'SAINT-plus (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_molecular_graphics    ORTEP-3
_computing_publication_material  ORTEP-3
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Smart ApexII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            31039
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.9932
_exptl_absorpt_correction_T_min  0.9751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         6265
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0438P)²+0.3410P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1050
_reflns_number_gt                4789
_reflns_number_total             6265
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0280_suppl.cif
_cod_data_source_block           p1bar
_cod_original_cell_volume        1259.56(13)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8107017
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.43856(15) 0.79636(15) 0.40541(13) 0.0377(3) Uani 1 1 d . . .
H1A H 0.4011 0.7035 0.3951 0.045 Uiso 1 1 calc R . .
H1B H 0.4540 0.8612 0.4960 0.045 Uiso 1 1 calc R . .
C2 C 0.56605(15) 0.82049(16) 0.37094(15) 0.0420(4) Uani 1 1 d . . .
H2A H 0.6302 0.9140 0.4285 0.050 Uiso 1 1 calc R . .
H2B H 0.6079 0.7574 0.3800 0.050 Uiso 1 1 calc R . .
C3 C 0.52600(13) 0.79676(13) 0.23264(13) 0.0316(3) Uani 1 1 d . . .
C4 C 0.38441(12) 0.79946(12) 0.19391(12) 0.0255(3) Uani 1 1 d . . .
C5 C 0.24153(13) 0.84484(12) 0.33558(12) 0.0290(3) Uani 1 1 d . . .
C6 C 0.05320(13) 0.89107(14) 0.23758(14) 0.0334(3) Uani 1 1 d . . .
C7 C 0.02039(16) 0.90371(17) 0.11263(15) 0.0453(4) Uani 1 1 d . . .
H7A H 0.0926 0.9795 0.1185 0.068 Uiso 1 1 calc R . .
H7B H -0.0629 0.9195 0.0993 0.068 Uiso 1 1 calc R . .
H7C H 0.0103 0.8203 0.0392 0.068 Uiso 1 1 calc R . .
C8 C 0.08550(18) 1.02444(16) 0.35487(16) 0.0478(4) Uani 1 1 d . . .
H8A H 0.1563 1.0956 0.3528 0.072 Uiso 1 1 calc R . .
H8B H 0.1153 1.0169 0.4349 0.072 Uiso 1 1 calc R . .
H8C H 0.0057 1.0467 0.3526 0.072 Uiso 1 1 calc R . .
C9 C -0.05556(17) 0.77512(19) 0.2333(2) 0.0606(5) Uani 1 1 d . . .
H9A H -0.0314 0.7698 0.3154 0.091 Uiso 1 1 calc R . .
H9B H -0.0662 0.6907 0.1610 0.091 Uiso 1 1 calc R . .
H9C H -0.1396 0.7898 0.2209 0.091 Uiso 1 1 calc R . .
C10 C 0.39995(13) 0.92741(13) 0.17549(13) 0.0300(3) Uani 1 1 d . . .
C11 C 0.34288(16) 1.01702(15) 0.03218(16) 0.0401(3) Uani 1 1 d . . .
H11A H 0.4362 1.0749 0.0515 0.048 Uiso 1 1 calc R . .
H11B H 0.3018 1.0714 0.0880 0.048 Uiso 1 1 calc R . .
C12 C 0.26638(18) 0.96177(19) -0.10826(18) 0.0513(4) Uani 1 1 d . . .
H12A H 0.2664 1.0363 -0.1289 0.077 Uiso 1 1 calc R . .
H12B H 0.1744 0.9047 -0.1259 0.077 Uiso 1 1 calc R . .
H12C H 0.3081 0.9080 -0.1621 0.077 Uiso 1 1 calc R . .
C13 C 0.28791(12) 0.66354(12) 0.07286(11) 0.0231(2) Uani 1 1 d . . .
H13 H 0.2001 0.6718 0.0470 0.028 Uiso 1 1 calc R . .
C14 C 0.26553(12) 0.54900(12) 0.11043(11) 0.0227(2) Uani 1 1 d . . .
C15 C 0.15865(12) 0.51297(12) 0.15408(12) 0.0256(3) Uani 1 1 d . . .
H15 H 0.0966 0.5562 0.1545 0.031 Uiso 1 1 calc R . .
C16 C 0.14118(13) 0.41482(13) 0.19699(13) 0.0296(3) Uani 1 1 d . . .
H16 H 0.0687 0.3911 0.2277 0.035 Uiso 1 1 calc R . .
C17 C 0.23202(14) 0.35297(13) 0.19373(12) 0.0300(3) Uani 1 1 d . . .
C19 C 0.33767(13) 0.38314(13) 0.14937(13) 0.0310(3) Uani 1 1 d . . .
H19 H 0.3981 0.3379 0.1475 0.037 Uiso 1 1 calc R . .
C20 C 0.35345(13) 0.48183(13) 0.10733(12) 0.0277(3) Uani 1 1 d . . .
H20 H 0.4256 0.5040 0.0758 0.033 Uiso 1 1 calc R . .
C21 C 0.25845(13) 0.60323(13) -0.15665(12) 0.0270(3) Uani 1 1 d . . .
C22 C 0.26953(14) 0.54951(15) -0.37779(12) 0.0335(3) Uani 1 1 d . . .
C23 C 0.20280(18) 0.63836(18) -0.40659(16) 0.0468(4) Uani 1 1 d . . .
H23A H 0.1262 0.6329 -0.3746 0.070 Uiso 1 1 calc R . .
H23B H 0.1724 0.6079 -0.5007 0.070 Uiso 1 1 calc R . .
H23C H 0.2666 0.7319 -0.3630 0.070 Uiso 1 1 calc R . .
C24 C 0.17390(17) 0.40492(16) -0.43370(15) 0.0458(4) Uani 1 1 d . . .
H24A H 0.2214 0.3516 -0.4125 0.069 Uiso 1 1 calc R . .
H24B H 0.1373 0.3675 -0.5284 0.069 Uiso 1 1 calc R . .
H24C H 0.1012 0.4022 -0.3963 0.069 Uiso 1 1 calc R . .
C25 C 0.38868(17) 0.5566(2) -0.42625(15) 0.0496(4) Uani 1 1 d . . .
H25A H 0.4309 0.4989 -0.4067 0.074 Uiso 1 1 calc R . .
H25B H 0.4530 0.6499 -0.3828 0.074 Uiso 1 1 calc R . .
H25C H 0.3591 0.5256 -0.5205 0.074 Uiso 1 1 calc R . .
N1 N 0.34957(11) 0.81729(11) 0.31155(10) 0.0281(2) Uani 1 1 d . . .
N2 N 0.33840(11) 0.63892(11) -0.03668(10) 0.0253(2) Uani 1 1 d . . .
O1 O 0.59043(10) 0.77795(11) 0.15893(10) 0.0415(2) Uani 1 1 d . . .
O2 O 0.17487(9) 0.85940(9) 0.23677(8) 0.0307(2) Uani 1 1 d . . .
O3 O 0.21327(11) 0.85492(11) 0.43304(10) 0.0414(2) Uani 1 1 d . . .
O4 O 0.46405(11) 1.03817(10) 0.26315(10) 0.0461(3) Uani 1 1 d . . .
O5 O 0.33850(10) 0.90094(9) 0.05540(9) 0.0336(2) Uani 1 1 d . . .
O6 O 0.33323(9) 0.60514(11) -0.23565(9) 0.0354(2) Uani 1 1 d . . .
O7 O 0.13928(9) 0.57375(11) -0.18683(9) 0.0387(2) Uani 1 1 d . . .
F1 F 0.21567(10) 0.25639(9) 0.23541(9) 0.0465(2) Uani 1 1 d . . .
H2 H 0.4211(17) 0.6668(15) -0.0204(15) 0.034(4) Uiso 1 1 d . . .
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
N1 C1 C2 103.41(11) . .
N1 C1 H1A 111.1 . .
C2 C1 H1A 111.1 . .
N1 C1 H1B 111.1 . .
C2 C1 H1B 111.1 . .
H1A C1 H1B 109.0 . .
C3 C2 C1 105.70(11) . .
C3 C2 H2A 110.6 . .
C1 C2 H2A 110.6 . .
C3 C2 H2B 110.6 . .
C1 C2 H2B 110.6 . .
H2A C2 H2B 108.7 . .
O1 C3 O1 0.00(16) 1 .
O1 C3 C2 127.17(13) 1 .
O1 C3 C2 127.17(13) . .
O1 C3 C4 123.35(12) 1 .
O1 C3 C4 123.35(12) . .
C2 C3 C4 109.48(11) . .
N1 C4 C10 108.96(10) . .
N1 C4 C3 101.49(10) . .
C10 C4 C3 107.29(10) . .
N1 C4 C13 112.60(10) . .
C10 C4 C13 115.18(10) . .
C3 C4 C13 110.32(10) . .
O3 C5 O2 126.64(13) . .
O3 C5 N1 123.42(13) . .
O2 C5 N1 109.94(10) . .
O2 C6 C9 109.39(12) . .
O2 C6 C7 101.73(11) . .
C9 C6 C7 111.55(14) . .
O2 C6 C8 109.94(11) . .
C9 C6 C8 112.97(14) . .
C7 C6 C8 110.68(13) . .
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C6 C8 H8A 109.5 . .
C6 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C6 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C6 C9 H9A 109.5 . .
C6 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C6 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
O4 C10 O5 125.02(13) . .
O4 C10 C4 121.75(12) . .
O5 C10 C4 113.23(11) . .
O5 C11 C12 106.29(12) . .
O5 C11 H11A 110.5 . .
C12 C11 H11A 110.5 . .
O5 C11 H11B 110.5 . .
C12 C11 H11B 110.5 . .
H11A C11 H11B 108.7 . .
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
N2 C13 C14 112.48(9) . .
N2 C13 C4 110.83(10) . .
C14 C13 C4 109.64(10) . .
N2 C13 H13 107.9 . .
C14 C13 H13 107.9 . .
C4 C13 H13 107.9 . .
C15 C14 C20 118.53(11) . .
C15 C14 C13 120.07(10) . .
C20 C14 C13 121.35(11) . .
C16 C15 C14 121.11(11) . .
C16 C15 H15 119.4 . .
C14 C15 H15 119.4 . .
C17 C16 C15 118.02(12) . .
C17 C16 H16 121.0 . .
C15 C16 H16 121.0 . .
F1 C17 C19 118.40(12) . .
F1 C17 C16 118.48(12) . .
C19 C17 C16 123.11(12) . .
C17 C19 C20 117.90(12) . .
C17 C19 H19 121.1 . .
C20 C19 H19 121.1 . .
C19 C20 C14 121.32(12) . .
C19 C20 H20 119.3 . .
C14 C20 H20 119.3 . .
O7 C21 O6 126.18(12) . .
O7 C21 N2 124.77(11) . .
O6 C21 N2 109.05(11) . .
O6 C22 C23 110.44(12) . .
O6 C22 C24 110.36(11) . .
C23 C22 C24 112.45(13) . .
O6 C22 C25 101.81(11) . .
C23 C22 C25 110.41(13) . .
C24 C22 C25 110.87(13) . .
C22 C23 H23A 109.5 . .
C22 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C22 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C22 C24 H24A 109.5 . .
C22 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
C22 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
C22 C25 H25A 109.5 . .
C22 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
C22 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
C5 N1 C4 125.22(10) . .
C5 N1 C1 120.36(11) . .
C4 N1 C1 114.36(10) . .
C21 N2 C13 120.98(11) . .
C21 N2 H2 119.4(10) . .
C13 N2 H2 117.6(10) . .
O1 O1 C3 0(10) 1 .
C5 O2 C6 121.59(10) . .
C10 O5 C11 116.35(11) . .
C21 O6 C22 120.69(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.4720(17) .
C1 C2 1.514(2) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 C3 1.495(2) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 O1 1.2099(17) 1
C3 O1 1.2099(17) .
C3 C4 1.5543(18) .
C4 N1 1.4540(15) .
C4 C10 1.5445(18) .
C4 C13 1.5691(17) .
C5 O3 1.2108(16) .
C5 O2 1.3467(16) .
C5 N1 1.3628(17) .
C6 O2 1.4828(15) .
C6 C9 1.513(2) .
C6 C7 1.515(2) .
C6 C8 1.520(2) .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 O4 1.1999(16) .
C10 O5 1.3214(16) .
C11 O5 1.4583(16) .
C11 C12 1.494(2) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 N2 1.4529(15) .
C13 C14 1.5216(17) .
C13 H13 1.0000 .
C14 C15 1.3917(17) .
C14 C20 1.3939(17) .
C15 C16 1.3892(18) .
C15 H15 0.9500 .
C16 C17 1.3770(19) .
C16 H16 0.9500 .
C17 F1 1.3628(15) .
C17 C19 1.3728(19) .
C19 C20 1.3883(18) .
C19 H19 0.9500 .
C20 H20 0.9500 .
C21 O7 1.2077(15) .
C21 O6 1.3499(15) .
C21 N2 1.3538(16) .
C22 O6 1.4823(15) .
C22 C23 1.514(2) .
C22 C24 1.515(2) .
C22 C25 1.517(2) .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
C25 H25A 0.9800 .
C25 H25B 0.9800 .
C25 H25C 0.9800 .
N2 H2 0.837(16) .
O1 O1 0.000(3) 1
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
C1 H1B O4 0.99 2.48 3.4109(18) 156.6 2_676
C2 H2A O3 0.99 2.44 3.4253(19) 178.9 2_676
C12 H12A O1 0.98 2.48 3.320(2) 143.4 2_675
C16 H16 O7 0.95 2.43 3.1095(16) 128.5 2_565
N2 H2 O1 0.837(16) 2.182(16) 2.8270(15) 133.9(14) 1
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
N1 C1 C2 C3 -22.82(14) . . . .
C1 C2 C3 O1 -163.50(14) . . . 1
C1 C2 C3 O1 -163.50(14) . . . .
C1 C2 C3 C4 16.48(15) . . . .
O1 C3 C4 N1 176.95(12) 1 . . .
O1 C3 C4 N1 176.95(12) . . . .
C2 C3 C4 N1 -3.04(13) . . . .
O1 C3 C4 C10 -68.81(15) 1 . . .
O1 C3 C4 C10 -68.81(15) . . . .
C2 C3 C4 C10 111.20(12) . . . .
O1 C3 C4 C13 57.38(16) 1 . . .
O1 C3 C4 C13 57.38(16) . . . .
C2 C3 C4 C13 -122.60(12) . . . .
N1 C4 C10 O4 47.56(17) . . . .
C3 C4 C10 O4 -61.56(16) . . . .
C13 C4 C10 O4 175.18(12) . . . .
N1 C4 C10 O5 -133.61(11) . . . .
C3 C4 C10 O5 117.26(12) . . . .
C13 C4 C10 O5 -5.99(15) . . . .
N1 C4 C13 N2 -170.51(10) . . . .
C10 C4 C13 N2 63.71(13) . . . .
C3 C4 C13 N2 -57.92(13) . . . .
N1 C4 C13 C14 -45.74(13) . . . .
C10 C4 C13 C14 -171.52(10) . . . .
C3 C4 C13 C14 66.86(12) . . . .
N2 C13 C14 C15 -144.18(11) . . . .
C4 C13 C14 C15 92.01(13) . . . .
N2 C13 C14 C20 38.51(15) . . . .
C4 C13 C14 C20 -85.30(13) . . . .
C20 C14 C15 C16 1.66(18) . . . .
C13 C14 C15 C16 -175.73(11) . . . .
C14 C15 C16 C17 -0.72(19) . . . .
C15 C16 C17 F1 -179.89(11) . . . .
C15 C16 C17 C19 -0.5(2) . . . .
F1 C17 C19 C20 -179.91(12) . . . .
C16 C17 C19 C20 0.7(2) . . . .
C17 C19 C20 C14 0.31(19) . . . .
C15 C14 C20 C19 -1.46(18) . . . .
C13 C14 C20 C19 175.90(12) . . . .
O3 C5 N1 C4 177.62(12) . . . .
O2 C5 N1 C4 -2.85(17) . . . .
O3 C5 N1 C1 0.74(19) . . . .
O2 C5 N1 C1 -179.73(11) . . . .
C10 C4 N1 C5 57.34(15) . . . .
C3 C4 N1 C5 170.34(11) . . . .
C13 C4 N1 C5 -71.73(15) . . . .
C10 C4 N1 C1 -125.62(12) . . . .
C3 C4 N1 C1 -12.63(13) . . . .
C13 C4 N1 C1 105.31(12) . . . .
C2 C1 N1 C5 -159.87(12) . . . .
C2 C1 N1 C4 22.93(15) . . . .
O7 C21 N2 C13 -9.1(2) . . . .
O6 C21 N2 C13 171.43(10) . . . .
C14 C13 N2 C21 105.12(13) . . . .
C4 C13 N2 C21 -131.73(12) . . . .
C2 C3 O1 O1 0.00(15) . . . 1
C4 C3 O1 O1 0.00(14) . . . 1
O3 C5 O2 C6 0.0(2) . . . .
N1 C5 O2 C6 -179.51(10) . . . .
C9 C6 O2 C5 -64.54(16) . . . .
C7 C6 O2 C5 177.37(12) . . . .
C8 C6 O2 C5 60.05(16) . . . .
O4 C10 O5 C11 -4.33(19) . . . .
C4 C10 O5 C11 176.89(10) . . . .
C12 C11 O5 C10 -179.41(12) . . . .
O7 C21 O6 C22 -9.3(2) . . . .
N2 C21 O6 C22 170.16(11) . . . .
C23 C22 O6 C21 69.78(16) . . . .
C24 C22 O6 C21 -55.18(16) . . . .
C25 C22 O6 C21 -172.95(12) . . . .
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{77a239d1-cdee-4b67-b9c9-612f14c2e791} y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{77a239d1-cdee-4b67-b9c9-612f14c2e791} '_publcif_info_datablock.publ_exptl'
{77a239d1-cdee-4b67-b9c9-612f14c2e791} '_geom_hbond_atom_site_label_D'
loop_
_publcif_info_cif.paper_type
EE
