#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/78/2007890.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_2007890
loop_
_publ_author_name
'Dijksma, Fokke J. J.'
'Gould, Robert O.'
'Parsons, Simon'
'Walkinshaw, Malcolm D.'
_publ_section_title
;
 Brucinium Hydrogen Fumarate Sesquihydrate and Brucinium Hydrogen
 Maleate
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1948
_journal_page_last               1951
_journal_paper_doi               10.1107/S0108270198010324
_journal_volume                  54
_journal_year                    1998
_chemical_formula_iupac          'C23 H27 N2 O4 , C4 H3 O4 , 3/2H2O'
_chemical_formula_moiety         'C23 H27 N2 O4 , C4 H3 O4 , 1.5 H2O'
_chemical_formula_sum            'C27 H33 N2 O9.5'
_chemical_formula_weight         537.55
_chemical_name_systematic
;
Brucinium Fumarate
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.27(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.349(3)
_cell_length_b                   12.298(3)
_cell_length_c                   15.173(3)
_cell_measurement_reflns_used    44
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      22
_cell_measurement_theta_min      20
_cell_volume                     2583.0(10)
_computing_cell_refinement       DIF4
_computing_data_collection       'DIF4 (Stoe & Cie, 1990a)'
_computing_data_reduction        'REDU4 (Stoe & Cie, 1990b)'
_computing_molecular_graphics
;
Cerius² (Molecular Simulations Inc., 1997) and SHELXTL
(Sheldrick, 1994)
;
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'DIRDIF96 (Beurskens, 1996)'
_diffrn_ambient_temperature      220(2)
_diffrn_measured_fraction_theta_full 0.482
_diffrn_measured_fraction_theta_max 0.482
_diffrn_measurement_device_type
;
Stoe Stadi-4 four-circle
diffractometer equipped with an Oxford Cryosystems low-temperature
device (Cosier & Glazer, 1986).
;
_diffrn_measurement_method
;
ω/θ scans with ω scan width (0.99 + 0.35 tanθ)°
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.012
_diffrn_reflns_av_sigmaI/netI    0.025
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3367
_diffrn_reflns_theta_full        70.04
_diffrn_reflns_theta_max         70
_diffrn_reflns_theta_min         3.02
_diffrn_standards_decay_%        <3
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.880
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1140
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.259
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       0.00110(11)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    'H atoms: see below'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         2711
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.046
_refine_ls_R_factor_gt           0.038
_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)+(0.0523P)²+1.1904P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.096
_reflns_number_gt                2416
_reflns_number_total             2711
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm1243.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (3 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_bond_publ_flag' value 'Y' changed to 'y'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (3
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (6
times).

'_geom_torsion_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (8 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0523P)^2^+1.1904P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0523P)^2^+1.1904P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        2582.8(9)
_cod_original_sg_symbol_H-M      'C 2'
_cod_original_formula_sum        'C27 H33 N2 O9.50'
_cod_database_code               2007890
_cod_database_fobs_code          2007890
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
loop_
_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.3320(2) -0.0437(2) 0.47362(19) 0.0248(6) Uani d . 1 . . C
C2 0.3942(2) -0.0917(3) 0.5504(2) 0.0272(7) Uani d . 1 . . C
H2 0.4277 -0.0495 0.6005 0.033 Uiso calc R 1 . . H
C3 0.40484(19) -0.2034(3) 0.5502(2) 0.0278(7) Uani d . 1 . . C
C4 0.3563(2) -0.2662(3) 0.4736(2) 0.0292(7) Uani d . 1 . . C
C5 0.2917(2) -0.2167(2) 0.4005(2) 0.0268(6) Uani d . 1 . . C
H5 0.2564 -0.2584 0.3510 0.032 Uiso calc R 1 . . H
C6 0.2798(2) -0.1046(3) 0.40120(19) 0.0259(6) Uani d . 1 . . C
C7 0.2108(2) -0.0331(3) 0.33421(19) 0.0259(6) Uani d . 1 . . C
C8 0.2505(2) 0.0827(2) 0.36241(17) 0.0242(6) Uani d . 1 . . C
H8 0.1966 0.1326 0.3632 0.029 Uiso calc R 1 . . H
C9 0.19798(19) -0.0600(3) 0.23229(18) 0.0280(6) Uani d . 1 . . C
H9 0.1987 -0.1400 0.2252 0.034 Uiso calc R 1 . . H
C10 0.0473(2) 0.0117(3) 0.2562(2) 0.0334(7) Uani d . 1 . . C
H10A -0.0197 -0.0140 0.2395 0.040 Uiso calc R 1 . . H
H10B 0.0476 0.0906 0.2653 0.040 Uiso calc R 1 . . H
C11 0.10533(19) -0.0450(3) 0.34135(19) 0.0289(6) Uani d . 1 . . C
H11A 0.0869 -0.1217 0.3418 0.035 Uiso calc R 1 . . H
H11B 0.0968 -0.0096 0.3966 0.035 Uiso calc R 1 . . H
C12 0.2729(2) -0.0112(3) 0.1900(2) 0.0305(7) Uani d . 1 . . C
H12A 0.2569 -0.0282 0.1246 0.037 Uiso calc R 1 . . H
H12B 0.3367 -0.0418 0.2190 0.037 Uiso calc R 1 . . H
C13 0.2744(2) 0.1118(3) 0.2037(2) 0.0291(7) Uani d . 1 . . C
H13 0.3193 0.1443 0.1714 0.035 Uiso calc R 1 . . H
C14 0.31409(19) 0.1325(3) 0.30670(19) 0.0264(6) Uani d . 1 . . C
H14 0.3767 0.0938 0.3254 0.032 Uiso calc R 1 . . H
C15 0.0980(2) 0.0742(3) 0.1181(2) 0.0360(7) Uani d . 1 . . C
H15A 0.1116 0.0456 0.0625 0.043 Uiso calc R 1 . . H
H15B 0.0344 0.1092 0.1010 0.043 Uiso calc R 1 . . H
C16 0.1736(2) 0.1560(3) 0.16196(19) 0.0313(7) Uani d . 1 . . C
C17 0.1529(2) 0.2619(3) 0.1637(2) 0.0377(8) Uani d . 1 . . C
H17 0.0901 0.2857 0.1343 0.045 Uiso calc R 1 . . H
C18 0.2266(3) 0.3441(3) 0.2112(2) 0.0429(8) Uani d . 1 . . C
H18A 0.2831 0.3404 0.1865 0.052 Uiso calc R 1 . . H
H18B 0.1992 0.4173 0.2000 0.052 Uiso calc R 1 . . H
C19 0.3351(2) 0.2505(3) 0.3382(2) 0.0302(7) Uani d . 1 . . C
H19 0.3910 0.2777 0.3179 0.036 Uiso calc R 1 . . H
C20 0.3581(2) 0.2580(2) 0.4440(2) 0.0296(7) Uani d . 1 . . C
H20A 0.4171 0.3011 0.4657 0.035 Uiso calc R 1 . . H
H20B 0.3056 0.2983 0.4594 0.035 Uiso calc R 1 . . H
C21 0.37166(19) 0.1526(3) 0.49669(19) 0.0271(6) Uani d . 1 . . C
C22 0.5140(2) -0.1971(3) 0.6969(2) 0.0399(8) Uani d . 1 . . C
H22A 0.5545 -0.1450 0.6762 0.060 Uiso calc R 1 . . H
H22B 0.5542 -0.2444 0.7425 0.060 Uiso calc R 1 . . H
H22C 0.4689 -0.1586 0.7233 0.060 Uiso calc R 1 . . H
C23 0.3414(3) -0.4369(3) 0.3985(2) 0.0491(9) Uani d . 1 . . C
H23A 0.2714 -0.4385 0.3824 0.074 Uiso calc R 1 . . H
H23B 0.3662 -0.5105 0.4088 0.074 Uiso calc R 1 . . H
H23C 0.3630 -0.4042 0.3491 0.074 Uiso calc R 1 . . H
N1 0.31406(17) 0.0691(2) 0.45686(16) 0.0257(5) Uani d . 1 . . N
N2 0.09728(17) -0.0178(2) 0.18362(17) 0.0307(6) Uani d . 1 . . N
H2A 0.0636 -0.0745 0.1504 0.037 Uiso calc R 1 . . H
O1 0.43006(15) 0.1447(2) 0.57296(14) 0.0384(5) Uani d . 1 . . O
O2 0.25567(16) 0.3235(2) 0.30782(14) 0.0367(5) Uani d . 1 . . O
O3 0.46157(14) -0.26089(19) 0.62077(14) 0.0348(5) Uani d . 1 . . O
O4 0.37633(16) -0.37449(18) 0.47972(16) 0.0366(5) Uani d . 1 . . O
O1F 0.50891(15) 0.2940(2) 0.11841(16) 0.0428(6) Uani d . 1 . . O
O2F 0.39714(18) 0.4154(2) 0.0624(2) 0.0563(8) Uani d . 1 . . O
O3F 0.2402(2) 0.0566(3) -0.0423(2) 0.0712(10) Uani d . 1 . . O
H3F 0.1956 0.0116 -0.0563 0.107 Uiso calc R 1 . . H
O4F 0.1226(3) 0.1771(4) -0.1067(3) 0.136(2) Uani d . 1 . . O
C1F 0.4267(2) 0.3200(3) 0.0705(2) 0.0357(7) Uani d . 1 . . C
C3F 0.2720(3) 0.2454(4) -0.0212(3) 0.0635(14) Uani d . 1 . . C
H13F 0.2479 0.3168 -0.0268 0.076 Uiso calc R 1 . . H
C2F 0.3634(2) 0.2297(4) 0.0235(2) 0.0435(9) Uani d . 1 . . C
H2F 0.3894 0.1593 0.0257 0.052 Uiso calc R 1 . . H
C4F 0.2051(3) 0.1555(5) -0.0633(3) 0.0770(18) Uani d . 1 . . C
O1W 0.5373(6) 0.0938(9) 0.2292(7) 0.100(3) Uani d P 0.50 A 1 O
H1WA 0.5460 0.1081 0.2856 0.150 Uiso d PR 0.50 A 1 H
H1WB 0.5284 0.1512 0.1969 0.150 Uiso d PR 0.50 A 1 H
O1W' 0.5957(7) 0.1268(9) 0.2419(6) 0.095(3) Uani d P 0.50 B 2 O
H1WC 0.5812 0.1270 0.2927 0.143 Uiso d PR 0.50 B 2 H
H1WD 0.5602 0.1728 0.2067 0.143 Uiso d PR 0.50 B 2 H
O2W -0.0296(6) 0.4566(8) 0.0876(6) 0.115(3) Uani d P 0.50 . . O
H2WA 0.0198 0.4620 0.0670 0.173 Uiso d PR 0.50 . . H
H2WB -0.0015 0.4999 0.1300 0.173 Uiso d PR 0.50 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_publ_flag
C6 C1 C2 122.0(3) ?
C6 C1 N1 110.6(2) ?
C2 C1 N1 127.3(3) ?
C3 C2 C1 117.6(3) ?
O3 C3 C2 123.9(3) y
O3 C3 C4 115.1(3) y
C2 C3 C4 120.9(3) ?
O4 C4 C5 124.7(3) y
O4 C4 C3 115.4(3) y
C5 C4 C3 119.9(3) ?
C4 C5 C6 119.2(3) ?
C1 C6 C5 120.2(3) ?
C1 C6 C7 110.2(3) ?
C5 C6 C7 129.5(3) ?
C6 C7 C9 115.9(2) ?
C6 C7 C8 102.8(2) ?
C9 C7 C8 114.2(2) ?
C6 C7 C11 112.3(2) ?
C9 C7 C11 100.9(2) ?
C8 C7 C11 111.2(2) ?
N1 C8 C14 105.9(2) ?
N1 C8 C7 104.4(2) ?
C14 C8 C7 116.5(2) ?
C12 C9 N2 110.3(2) ?
C12 C9 C7 115.4(2) ?
N2 C9 C7 105.0(2) ?
N2 C10 C11 104.6(2) ?
C10 C11 C7 103.0(2) ?
C9 C12 C13 108.7(3) ?
C16 C13 C12 108.7(3) ?
C16 C13 C14 114.9(2) ?
C12 C13 C14 107.0(2) ?
C8 C14 C19 107.8(2) ?
C8 C14 C13 112.4(2) ?
C19 C14 C13 117.6(3) ?
C16 C15 N2 109.9(2) ?
C17 C16 C15 121.5(3) ?
C17 C16 C13 122.2(3) ?
C15 C16 C13 116.3(3) ?
C16 C17 C18 122.1(3) ?
O2 C18 C17 110.4(3) ?
O2 C19 C14 114.8(2) ?
O2 C19 C20 103.3(2) ?
C14 C19 C20 110.4(2) ?
C21 C20 C19 117.4(3) ?
O1 C21 N1 122.6(3) ?
O1 C21 C20 121.5(3) ?
N1 C21 C20 115.9(2) ?
C21 N1 C1 126.8(2) ?
C21 N1 C8 119.3(2) ?
C1 N1 C8 108.5(2) ?
C15 N2 C10 112.8(2) ?
C15 N2 C9 113.8(2) ?
C10 N2 C9 107.4(2) ?
C19 O2 C18 115.6(3) ?
C3 O3 C22 115.3(3) y
C4 O4 C23 116.7(3) y
O2F C1F O1F 122.9(3) ?
O2F C1F C2F 120.4(3) ?
O1F C1F C2F 116.7(3) ?
C2F C3F C4F 123.4(5) ?
C3F C2F C1F 122.2(4) ?
O4F C4F O3F 125.7(5) ?
O4F C4F C3F 119.4(6) ?
O3F C4F C3F 114.6(3) ?
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
C1 C6 . 1.377(4) ?
C1 C2 . 1.398(4) ?
C1 N1 . 1.422(4) ?
C2 C3 . 1.382(5) ?
C3 O3 . 1.360(3) ?
C3 C4 . 1.416(4) ?
C4 O4 . 1.360(4) ?
C4 C5 . 1.385(4) ?
C5 C6 . 1.390(4) ?
C6 C7 . 1.502(4) ?
C7 C9 . 1.544(4) ?
C7 C8 . 1.552(4) ?
C7 C11 . 1.552(4) ?
C8 N1 . 1.492(3) ?
C8 C14 . 1.526(4) ?
C9 C12 . 1.514(4) ?
C9 N2 . 1.530(4) y
C10 N2 . 1.509(4) y
C10 C11 . 1.510(4) ?
C12 C13 . 1.525(5) ?
C13 C16 . 1.518(4) ?
C13 C14 . 1.537(4) ?
C14 C19 . 1.533(5) ?
C15 C16 . 1.501(5) ?
C15 N2 . 1.507(4) y
C16 C17 . 1.338(5) ?
C17 C18 . 1.503(5) ?
C18 O2 . 1.437(4) ?
C19 O2 . 1.428(4) ?
C19 C20 . 1.555(4) ?
C20 C21 . 1.508(4) ?
C21 O1 . 1.241(3) ?
C21 N1 . 1.356(4) ?
C22 O3 . 1.435(4) ?
C23 O4 . 1.426(4) ?
O1F C1F . 1.253(4) ?
O2F C1F . 1.243(5) ?
O3F C4F . 1.322(7) ?
O4F C4F . 1.223(5) ?
C1F C2F . 1.492(5) ?
C3F C2F . 1.323(5) ?
C3F C4F . 1.493(7) ?
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
N2 H2A O1F 3_445 0.92 1.81 2.699(4) 162.5
N2 H2A O2F 3_445 0.92 2.41 3.086(4) 130.0
O3F H3F O2F 4_545 0.83 1.76 2.583(4) 168.5
O1W' H1WC O1 2_656 0.85 2.10 2.937(10) 168.9
O1W' H1WD O1F . 0.85 2.01 2.839(10) 165.2
O1W H1WA O1 2_656 0.85 2.13 2.980(11) 179.2
O1W H1WB O1F . 0.85 2.10 2.949(12) 179.0
O2W H2WA O2W 2 0.85 2.39 2.996(18) 129.1
O2W H2WB O1W 3_455 0.85 1.86 2.702(14) 168.8
O2W H2WB O1W' 3_455 0.85 2.45 3.298(14) 172.7
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_publ_flag
C6 C1 C2 C3 2.4(4) ?
N1 C1 C2 C3 -176.4(3) ?
C1 C2 C3 O3 -178.9(2) y
C1 C2 C3 C4 1.7(4) ?
O3 C3 C4 O4 -2.6(4) ?
C2 C3 C4 O4 176.8(3) y
O3 C3 C4 C5 175.7(3) y
C2 C3 C4 C5 -4.8(4) ?
O4 C4 C5 C6 -178.1(3) y
C3 C4 C5 C6 3.8(4) ?
C2 C1 C6 C5 -3.5(4) ?
N1 C1 C6 C5 175.5(3) ?
C2 C1 C6 C7 173.2(3) ?
N1 C1 C6 C7 -7.8(3) ?
C4 C5 C6 C1 0.3(5) ?
C4 C5 C6 C7 -175.7(3) ?
C1 C6 C7 C9 141.5(3) ?
C5 C6 C7 C9 -42.2(4) ?
C1 C6 C7 C8 16.2(3) ?
C5 C6 C7 C8 -167.5(3) ?
C1 C6 C7 C11 -103.3(3) ?
C5 C6 C7 C11 73.0(4) ?
C6 C7 C8 N1 -18.0(3) ?
C9 C7 C8 N1 -144.3(2) ?
C11 C7 C8 N1 102.3(2) ?
C6 C7 C8 C14 98.4(3) ?
C9 C7 C8 C14 -27.9(3) ?
C11 C7 C8 C14 -141.3(2) ?
C6 C7 C9 C12 -84.1(3) ?
C8 C7 C9 C12 35.1(3) ?
C11 C7 C9 C12 154.4(3) ?
C6 C7 C9 N2 154.2(3) ?
C8 C7 C9 N2 -86.6(3) ?
C11 C7 C9 N2 32.8(3) ?
N2 C10 C11 C7 37.8(3) ?
C6 C7 C11 C10 -167.5(3) ?
C9 C7 C11 C10 -43.6(3) ?
C8 C7 C11 C10 78.0(3) ?
N2 C9 C12 C13 63.0(3) ?
C7 C9 C12 C13 -55.8(3) ?
C9 C12 C13 C16 -57.0(3) ?
C9 C12 C13 C14 67.6(3) ?
N1 C8 C14 C19 -71.1(3) ?
C7 C8 C14 C19 173.4(2) ?
N1 C8 C14 C13 157.7(2) ?
C7 C8 C14 C13 42.1(3) ?
C16 C13 C14 C8 59.3(4) ?
C12 C13 C14 C8 -61.4(3) ?
C16 C13 C14 C19 -66.7(4) ?
C12 C13 C14 C19 172.5(3) ?
N2 C15 C16 C17 -128.5(3) ?
N2 C15 C16 C13 51.6(3) ?
C12 C13 C16 C17 179.9(3) ?
C14 C13 C16 C17 60.1(4) ?
C12 C13 C16 C15 -0.2(4) ?
C14 C13 C16 C15 -120.0(3) ?
C15 C16 C17 C18 177.0(3) ?
C13 C16 C17 C18 -3.1(5) ?
C16 C17 C18 O2 -64.4(4) ?
C8 C14 C19 O2 -73.9(3) ?
C13 C14 C19 O2 54.4(4) ?
C8 C14 C19 C20 42.4(3) ?
C13 C14 C19 C20 170.6(2) ?
O2 C19 C20 C21 132.6(3) ?
C14 C19 C20 C21 9.4(4) ?
C19 C20 C21 O1 145.8(3) ?
C19 C20 C21 N1 -36.3(4) ?
O1 C21 N1 C1 -25.0(5) ?
C20 C21 N1 C1 157.2(3) ?
O1 C21 N1 C8 -175.9(3) ?
C20 C21 N1 C8 6.2(4) ?
C6 C1 N1 C21 -158.2(3) ?
C2 C1 N1 C21 20.8(5) ?
C6 C1 N1 C8 -4.7(3) ?
C2 C1 N1 C8 174.3(3) ?
C14 C8 N1 C21 46.7(3) ?
C7 C8 N1 C21 170.3(2) ?
C14 C8 N1 C1 -109.0(3) ?
C7 C8 N1 C1 14.5(3) ?
C16 C15 N2 C10 77.3(3) ?
C16 C15 N2 C9 -45.3(3) ?
C11 C10 N2 C15 -143.2(3) ?
C11 C10 N2 C9 -17.0(3) ?
C12 C9 N2 C15 -9.8(3) ?
C7 C9 N2 C15 115.2(3) ?
C12 C9 N2 C10 -135.4(3) ?
C7 C9 N2 C10 -10.5(3) ?
C14 C19 O2 C18 -67.5(4) ?
C20 C19 O2 C18 172.2(3) ?
C17 C18 O2 C19 88.8(3) ?
C2 C3 O3 C22 -2.0(4) y
C4 C3 O3 C22 177.4(3) y
C5 C4 O4 C23 11.7(5) y
C3 C4 O4 C23 -170.0(3) y
C4F C3F C2F C1F -175.6(4) ?
O2F C1F C2F C3F -6.1(5) ?
O1F C1F C2F C3F 173.0(3) ?
C2F C3F C4F O4F -177.1(4) ?
C2F C3F C4F O3F 8.6(6) ?
