#------------------------------------------------------------------------------
#$Date: 2020-11-06 15:10:27 +0200 (Fri, 06 Nov 2020) $
#$Revision: 258962 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/77/7157725.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_7157725
loop_
_publ_author_name
'Chen, Suo'
'Ruan, Yao'
'Lu, Ji-Liang'
'Hunter, Luke'
'Hu, Xiang-Guo'
_publ_section_title
;
 Diastereoselective synthesis and conformational analysis of
 4,5-difluoropipecolic acids.
;
_journal_issue                   40
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8192
_journal_page_last               8198
_journal_paper_doi               10.1039/d0ob01811b
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         C17H22FNO3
_chemical_formula_sum            'C17 H22 F N O3'
_chemical_formula_weight         307.35
_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   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-08-20 deposited with the CCDC.	2020-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                98.164(11)
_cell_angle_beta                 91.884(11)
_cell_angle_gamma                90.183(12)
_cell_formula_units_Z            4
_cell_length_a                   8.6569(13)
_cell_length_b                   11.7473(17)
_cell_length_c                   16.347(2)
_cell_measurement_reflns_used    3308
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.4700
_cell_measurement_theta_min      3.9500
_cell_volume                     1644.6(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0767
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12593
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         3.331
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_transmission_factor_max   1.0000
_exptl_transmission_factor_min   0.6587
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         6127
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1611
_refine_ls_R_factor_gt           0.1030
_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)+(0.1429P)²+1.2648P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2644
_refine_ls_wR_factor_ref         0.3163
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3463
_reflns_number_total             6127
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob01811b2.cif
_cod_data_source_block           RY20180528
_cod_depositor_comments
'Adding full bibliography for 7157725--7157727.cif.'
_cod_database_code               7157725
_shelx_shelxl_version_number     2014/7
_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   0.984
_shelx_estimated_absorpt_t_max   0.989
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 0.1588(5) 0.3081(3) 0.9252(2) 0.1021(12) Uani 1 1 d . . . . .
O1 O 0.4287(4) -0.1944(3) 0.4962(2) 0.0742(10) Uani 1 1 d . . . . .
O2 O -0.1394(4) 0.0852(3) 0.7169(2) 0.0661(9) Uani 1 1 d . . . . .
O3 O -0.0746(4) 0.0338(3) 0.84264(19) 0.0563(8) Uani 1 1 d . . . . .
N1 N 0.0954(4) 0.1311(3) 0.7793(2) 0.0492(9) Uani 1 1 d . . . . .
C1 C 0.3382(8) -0.2617(5) 0.4327(4) 0.092(2) Uani 1 1 d . . . . .
H1A H 0.2917 -0.2124 0.3969 0.138 Uiso 1 1 calc R U . . .
H1B H 0.2588 -0.3017 0.4571 0.138 Uiso 1 1 calc R U . . .
H1C H 0.4032 -0.3165 0.4012 0.138 Uiso 1 1 calc R U . . .
C2 C 0.3588(6) -0.1052(4) 0.5440(3) 0.0558(12) Uani 1 1 d . . . . .
C3 C 0.1999(6) -0.0847(4) 0.5396(3) 0.0606(13) Uani 1 1 d . . . . .
H3 H 0.1359 -0.1322 0.5026 0.073 Uiso 1 1 calc R U . . .
C4 C 0.1389(6) 0.0070(4) 0.5907(3) 0.0594(12) Uani 1 1 d . . . . .
H4 H 0.0336 0.0214 0.5865 0.071 Uiso 1 1 calc R U . . .
C5 C 0.2299(5) 0.0778(4) 0.6478(3) 0.0500(11) Uani 1 1 d . . . . .
C6 C 0.3880(6) 0.0558(5) 0.6502(3) 0.0619(13) Uani 1 1 d . . . . .
H6 H 0.4527 0.1035 0.6867 0.074 Uiso 1 1 calc R U . . .
C7 C 0.4504(6) -0.0351(5) 0.5997(3) 0.0631(13) Uani 1 1 d . . . . .
H7 H 0.5559 -0.0490 0.6036 0.076 Uiso 1 1 calc R U . . .
C8 C 0.1547(6) 0.1740(4) 0.7059(3) 0.0541(12) Uani 1 1 d . . . . .
H8 H 0.0666 0.2024 0.6757 0.065 Uiso 1 1 calc R U . . .
C9 C 0.2072(5) 0.1276(4) 0.8474(3) 0.0505(11) Uani 1 1 d . . . . .
H9A H 0.2905 0.0761 0.8293 0.061 Uiso 1 1 calc R U . . .
H9B H 0.1575 0.0981 0.8925 0.061 Uiso 1 1 calc R U . . .
C10 C 0.2714(7) 0.2441(4) 0.8770(3) 0.0666(14) Uani 1 1 d . . . . .
H10 H 0.3642 0.2368 0.9119 0.080 Uiso 1 1 calc R U . . .
C11 C 0.3119(6) 0.3065(4) 0.8087(4) 0.0677(14) Uani 1 1 d . . . . .
H11 H 0.3745 0.3717 0.8202 0.081 Uiso 1 1 calc R U . . .
C12 C 0.2632(6) 0.2737(4) 0.7322(3) 0.0641(14) Uani 1 1 d . . . . .
H12 H 0.2978 0.3146 0.6916 0.077 Uiso 1 1 calc R U . . .
C13 C -0.0483(5) 0.0831(4) 0.7753(3) 0.0495(11) Uani 1 1 d . . . . .
C14 C -0.2229(5) -0.0218(4) 0.8533(3) 0.0556(12) Uani 1 1 d . . . . .
C15 C -0.3519(7) 0.0675(6) 0.8605(4) 0.0900(19) Uani 1 1 d . . . . .
H15A H -0.3587 0.1027 0.8110 0.135 Uiso 1 1 calc R U . . .
H15B H -0.3294 0.1254 0.9071 0.135 Uiso 1 1 calc R U . . .
H15C H -0.4484 0.0306 0.8680 0.135 Uiso 1 1 calc R U . . .
C16 C -0.1975(7) -0.0653(6) 0.9359(3) 0.0842(18) Uani 1 1 d . . . . .
H16A H -0.1801 -0.0012 0.9787 0.126 Uiso 1 1 calc R U . . .
H16B H -0.1092 -0.1147 0.9335 0.126 Uiso 1 1 calc R U . . .
H16C H -0.2873 -0.1075 0.9478 0.126 Uiso 1 1 calc R U . . .
C17 C -0.2557(8) -0.1188(5) 0.7853(4) 0.0897(19) Uani 1 1 d . . . . .
H17A H -0.1728 -0.1731 0.7836 0.135 Uiso 1 1 calc R U . . .
H17B H -0.2645 -0.0895 0.7334 0.135 Uiso 1 1 calc R U . . .
H17C H -0.3507 -0.1560 0.7952 0.135 Uiso 1 1 calc R U . . .
F2 F 0.6023(5) 0.1926(3) 0.0696(2) 0.1013(12) Uani 1 1 d . . . . .
O4 O 0.9284(4) 0.6897(3) 0.5017(2) 0.0737(10) Uani 1 1 d . . . . .
O5 O 0.3815(4) 0.4682(3) 0.15487(18) 0.0565(8) Uani 1 1 d . . . . .
O6 O 0.3306(4) 0.4140(3) 0.2803(2) 0.0632(9) Uani 1 1 d . . . . .
N2 N 0.5576(4) 0.3684(3) 0.2176(2) 0.0500(9) Uani 1 1 d . . . . .
C18 C 0.8482(8) 0.7553(5) 0.5661(4) 0.0881(19) Uani 1 1 d . . . . .
H18A H 0.7616 0.7922 0.5430 0.132 Uiso 1 1 calc R U . . .
H18B H 0.9165 0.8126 0.5956 0.132 Uiso 1 1 calc R U . . .
H18C H 0.8121 0.7056 0.6033 0.132 Uiso 1 1 calc R U . . .
C19 C 0.8513(6) 0.6014(4) 0.4542(3) 0.0550(12) Uani 1 1 d . . . . .
C20 C 0.9357(6) 0.5308(5) 0.3976(3) 0.0633(13) Uani 1 1 d . . . . .
H20 H 1.0410 0.5445 0.3942 0.076 Uiso 1 1 calc R U . . .
C21 C 0.8673(6) 0.4414(4) 0.3466(3) 0.0615(13) Uani 1 1 d . . . . .
H21 H 0.9270 0.3948 0.3094 0.074 Uiso 1 1 calc R U . . .
C22 C 0.7089(5) 0.4187(4) 0.3494(3) 0.0491(11) Uani 1 1 d . . . . .
C23 C 0.6281(6) 0.4891(4) 0.4072(3) 0.0580(12) Uani 1 1 d . . . . .
H23 H 0.5231 0.4753 0.4116 0.070 Uiso 1 1 calc R U . . .
C24 C 0.6966(6) 0.5790(4) 0.4587(3) 0.0600(13) Uani 1 1 d . . . . .
H24 H 0.6377 0.6248 0.4968 0.072 Uiso 1 1 calc R U . . .
C25 C 0.6257(5) 0.3244(4) 0.2910(3) 0.0521(11) Uani 1 1 d . . . . .
H25 H 0.5409 0.2957 0.3209 0.062 Uiso 1 1 calc R U . . .
C26 C 0.7286(6) 0.2243(4) 0.2632(3) 0.0655(14) Uani 1 1 d . . . . .
H26 H 0.7662 0.1821 0.3035 0.079 Uiso 1 1 calc R U . . .
C27 C 0.7699(7) 0.1914(4) 0.1871(4) 0.0712(15) Uani 1 1 d . . . . .
H27 H 0.8319 0.1269 0.1757 0.085 Uiso 1 1 calc R U . . .
C28 C 0.7192(6) 0.2556(4) 0.1183(3) 0.0669(14) Uani 1 1 d . . . . .
H28 H 0.8076 0.2641 0.0837 0.080 Uiso 1 1 calc R U . . .
C29 C 0.6599(6) 0.3718(4) 0.1493(3) 0.0549(12) Uani 1 1 d . . . . .
H29A H 0.7462 0.4230 0.1674 0.066 Uiso 1 1 calc R U . . .
H29B H 0.6044 0.4020 0.1047 0.066 Uiso 1 1 calc R U . . .
C30 C 0.4128(5) 0.4170(4) 0.2219(3) 0.0496(11) Uani 1 1 d . . . . .
C33 C 0.1034(7) 0.4330(5) 0.1342(4) 0.0802(16) Uani 1 1 d . . . . .
H33A H 0.1263 0.3740 0.0894 0.120 Uiso 1 1 calc R U . . .
H33B H 0.0063 0.4675 0.1226 0.120 Uiso 1 1 calc R U . . .
H33C H 0.0975 0.3998 0.1844 0.120 Uiso 1 1 calc R U . . .
C34 C 0.2492(7) 0.5696(5) 0.0631(3) 0.0777(16) Uani 1 1 d . . . . .
H34A H 0.3352 0.6222 0.0684 0.117 Uiso 1 1 calc R U . . .
H34B H 0.1569 0.6089 0.0493 0.117 Uiso 1 1 calc R U . . .
H34C H 0.2677 0.5069 0.0202 0.117 Uiso 1 1 calc R U . . .
C35 C 0.2297(6) 0.5237(4) 0.1439(3) 0.0581(12) Uani 1 1 d . . . . .
C36 C 0.2067(8) 0.6195(5) 0.2138(4) 0.0852(18) Uani 1 1 d . . . . .
H36A H 0.1966 0.5879 0.2644 0.128 Uiso 1 1 calc R U . . .
H36B H 0.1148 0.6610 0.2027 0.128 Uiso 1 1 calc R U . . .
H36C H 0.2941 0.6709 0.2189 0.128 Uiso 1 1 calc R U . . .
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'
F F 0.0171 0.0103 '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'
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
C2 O1 C1 118.2(4) . . ?
C13 O3 C14 121.4(3) . . ?
C13 N1 C9 124.2(3) . . ?
C13 N1 C8 119.4(4) . . ?
C9 N1 C8 115.7(4) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 O1 117.5(5) . . ?
C7 C2 C3 119.2(5) . . ?
O1 C2 C3 123.3(4) . . ?
C4 C3 C2 119.4(5) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C5 C4 C3 121.9(5) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 117.3(4) . . ?
C4 C5 C8 119.6(4) . . ?
C6 C5 C8 123.1(4) . . ?
C7 C6 C5 121.4(5) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C2 C7 C6 120.7(5) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
N1 C8 C12 109.8(4) . . ?
N1 C8 C5 111.4(3) . . ?
C12 C8 C5 112.3(4) . . ?
N1 C8 H8 107.7 . . ?
C12 C8 H8 107.7 . . ?
C5 C8 H8 107.7 . . ?
N1 C9 C10 110.8(4) . . ?
N1 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
F1 C10 C11 108.9(4) . . ?
F1 C10 C9 108.4(4) . . ?
C11 C10 C9 112.5(4) . . ?
F1 C10 H10 109.0 . . ?
C11 C10 H10 109.0 . . ?
C9 C10 H10 109.0 . . ?
C12 C11 C10 122.5(5) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 H11 118.8 . . ?
C11 C12 C8 124.2(4) . . ?
C11 C12 H12 117.9 . . ?
C8 C12 H12 117.9 . . ?
O2 C13 O3 125.4(4) . . ?
O2 C13 N1 123.2(4) . . ?
O3 C13 N1 111.4(4) . . ?
O3 C14 C17 111.2(4) . . ?
O3 C14 C16 102.4(4) . . ?
C17 C14 C16 111.2(4) . . ?
O3 C14 C15 110.0(4) . . ?
C17 C14 C15 112.3(5) . . ?
C16 C14 C15 109.3(5) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 O4 C18 118.0(4) . . ?
C30 O5 C35 120.6(3) . . ?
C30 N2 C29 124.2(4) . . ?
C30 N2 C25 119.2(3) . . ?
C29 N2 C25 116.0(4) . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 C24 124.4(4) . . ?
O4 C19 C20 117.2(4) . . ?
C24 C19 C20 118.4(5) . . ?
C21 C20 C19 121.2(5) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 121.1(5) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C23 C22 C21 116.5(4) . . ?
C23 C22 C25 120.3(4) . . ?
C21 C22 C25 123.2(4) . . ?
C24 C23 C22 122.5(5) . . ?
C24 C23 H23 118.7 . . ?
C22 C23 H23 118.7 . . ?
C19 C24 C23 120.3(5) . . ?
C19 C24 H24 119.8 . . ?
C23 C24 H24 119.9 . . ?
N2 C25 C26 109.2(4) . . ?
N2 C25 C22 111.7(3) . . ?
C26 C25 C22 112.7(4) . . ?
N2 C25 H25 107.7 . . ?
C26 C25 H25 107.7 . . ?
C22 C25 H25 107.7 . . ?
C27 C26 C25 125.7(5) . . ?
C27 C26 H26 117.1 . . ?
C25 C26 H26 117.1 . . ?
C26 C27 C28 121.2(5) . . ?
C26 C27 H27 119.4 . . ?
C28 C27 H27 119.4 . . ?
F2 C28 C29 109.0(4) . . ?
F2 C28 C27 109.4(4) . . ?
C29 C28 C27 112.3(4) . . ?
F2 C28 H28 108.7 . . ?
C29 C28 H28 108.7 . . ?
C27 C28 H28 108.7 . . ?
N2 C29 C28 111.5(4) . . ?
N2 C29 H29A 109.3 . . ?
C28 C29 H29A 109.3 . . ?
N2 C29 H29B 109.3 . . ?
C28 C29 H29B 109.3 . . ?
H29A C29 H29B 108.0 . . ?
O6 C30 O5 126.8(4) . . ?
O6 C30 N2 122.7(4) . . ?
O5 C30 N2 110.4(4) . . ?
C35 C33 H33A 109.5 . . ?
C35 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C35 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C35 C34 H34A 109.5 . . ?
C35 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C35 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
O5 C35 C36 110.1(4) . . ?
O5 C35 C34 101.6(4) . . ?
C36 C35 C34 111.4(4) . . ?
O5 C35 C33 109.2(4) . . ?
C36 C35 C33 113.9(5) . . ?
C34 C35 C33 110.0(4) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 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 1.423(6) . ?
O1 C2 1.370(6) . ?
O1 C1 1.423(7) . ?
O2 C13 1.221(5) . ?
O3 C13 1.340(5) . ?
O3 C14 1.465(5) . ?
N1 C13 1.361(6) . ?
N1 C9 1.457(5) . ?
N1 C8 1.472(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.369(7) . ?
C2 C3 1.398(7) . ?
C3 C4 1.383(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(7) . ?
C5 C8 1.530(6) . ?
C6 C7 1.377(7) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C12 1.503(7) . ?
C8 H8 0.9800 . ?
C9 C10 1.485(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.472(7) . ?
C10 H10 0.9800 . ?
C11 C12 1.311(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C14 C17 1.493(7) . ?
C14 C16 1.521(7) . ?
C14 C15 1.531(7) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
F2 C28 1.408(6) . ?
O4 C19 1.363(6) . ?
O4 C18 1.416(6) . ?
O5 C30 1.343(5) . ?
O5 C35 1.486(6) . ?
O6 C30 1.214(5) . ?
N2 C30 1.379(6) . ?
N2 C29 1.452(5) . ?
N2 C25 1.479(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C24 1.370(7) . ?
C19 C20 1.381(7) . ?
C20 C21 1.365(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.399(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.375(6) . ?
C22 C25 1.519(6) . ?
C23 C24 1.373(7) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.505(7) . ?
C25 H25 0.9800 . ?
C26 C27 1.311(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.496(7) . ?
C27 H27 0.9300 . ?
C28 C29 1.486(7) . ?
C28 H28 0.9800 . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C33 C35 1.514(7) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 C35 1.510(7) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 C36 1.504(7) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
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
C1 O1 C2 C7 -174.3(5) . . . . ?
C1 O1 C2 C3 7.2(7) . . . . ?
C7 C2 C3 C4 1.0(7) . . . . ?
O1 C2 C3 C4 179.5(4) . . . . ?
C2 C3 C4 C5 -1.6(7) . . . . ?
C3 C4 C5 C6 2.1(7) . . . . ?
C3 C4 C5 C8 -176.8(4) . . . . ?
C4 C5 C6 C7 -2.1(7) . . . . ?
C8 C5 C6 C7 176.8(4) . . . . ?
O1 C2 C7 C6 -179.6(4) . . . . ?
C3 C2 C7 C6 -1.0(7) . . . . ?
C5 C6 C7 C2 1.6(8) . . . . ?
C13 N1 C8 C12 149.5(4) . . . . ?
C9 N1 C8 C12 -39.8(5) . . . . ?
C13 N1 C8 C5 -85.4(5) . . . . ?
C9 N1 C8 C5 85.3(5) . . . . ?
C4 C5 C8 N1 84.5(5) . . . . ?
C6 C5 C8 N1 -94.3(5) . . . . ?
C4 C5 C8 C12 -151.8(4) . . . . ?
C6 C5 C8 C12 29.3(6) . . . . ?
C13 N1 C9 C10 -130.5(5) . . . . ?
C8 N1 C9 C10 59.3(5) . . . . ?
N1 C9 C10 F1 76.3(5) . . . . ?
N1 C9 C10 C11 -44.1(6) . . . . ?
F1 C10 C11 C12 -105.3(6) . . . . ?
C9 C10 C11 C12 14.9(8) . . . . ?
C10 C11 C12 C8 3.5(8) . . . . ?
N1 C8 C12 C11 8.2(7) . . . . ?
C5 C8 C12 C11 -116.3(5) . . . . ?
C14 O3 C13 O2 -1.5(7) . . . . ?
C14 O3 C13 N1 178.8(4) . . . . ?
C9 N1 C13 O2 -178.7(4) . . . . ?
C8 N1 C13 O2 -8.8(7) . . . . ?
C9 N1 C13 O3 1.0(6) . . . . ?
C8 N1 C13 O3 170.8(3) . . . . ?
C13 O3 C14 C17 60.3(5) . . . . ?
C13 O3 C14 C16 179.2(4) . . . . ?
C13 O3 C14 C15 -64.7(5) . . . . ?
C18 O4 C19 C24 7.2(7) . . . . ?
C18 O4 C19 C20 -173.2(5) . . . . ?
O4 C19 C20 C21 -179.0(4) . . . . ?
C24 C19 C20 C21 0.7(7) . . . . ?
C19 C20 C21 C22 0.5(8) . . . . ?
C20 C21 C22 C23 -1.5(7) . . . . ?
C20 C21 C22 C25 176.6(4) . . . . ?
C21 C22 C23 C24 1.4(7) . . . . ?
C25 C22 C23 C24 -176.8(4) . . . . ?
O4 C19 C24 C23 178.8(4) . . . . ?
C20 C19 C24 C23 -0.8(7) . . . . ?
C22 C23 C24 C19 -0.3(7) . . . . ?
C30 N2 C25 C26 149.0(4) . . . . ?
C29 N2 C25 C26 -39.6(5) . . . . ?
C30 N2 C25 C22 -85.7(5) . . . . ?
C29 N2 C25 C22 85.7(5) . . . . ?
C23 C22 C25 N2 84.7(5) . . . . ?
C21 C22 C25 N2 -93.4(5) . . . . ?
C23 C22 C25 C26 -152.0(4) . . . . ?
C21 C22 C25 C26 30.0(6) . . . . ?
N2 C25 C26 C27 9.2(7) . . . . ?
C22 C25 C26 C27 -115.6(6) . . . . ?
C25 C26 C27 C28 1.8(8) . . . . ?
C26 C27 C28 F2 -105.2(6) . . . . ?
C26 C27 C28 C29 15.9(7) . . . . ?
C30 N2 C29 C28 -129.9(5) . . . . ?
C25 N2 C29 C28 59.2(5) . . . . ?
F2 C28 C29 N2 77.0(5) . . . . ?
C27 C28 C29 N2 -44.3(6) . . . . ?
C35 O5 C30 O6 -3.5(7) . . . . ?
C35 O5 C30 N2 178.1(4) . . . . ?
C29 N2 C30 O6 -179.1(4) . . . . ?
C25 N2 C30 O6 -8.5(7) . . . . ?
C29 N2 C30 O5 -0.6(6) . . . . ?
C25 N2 C30 O5 170.0(3) . . . . ?
C30 O5 C35 C36 61.0(5) . . . . ?
C30 O5 C35 C34 179.0(4) . . . . ?
C30 O5 C35 C33 -64.8(5) . . . . ?
