#------------------------------------------------------------------------------
#$Date: 2020-05-29 02:24:59 +0300 (Fri, 29 May 2020) $
#$Revision: 252447 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/84/4038429.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_4038429
loop_
_publ_author_name
'Magnus, Nicholas Andrew'
'Buser, Jonas Y.'
'Embry, Matthew C.'
'Kallman, Neil John'
_publ_section_title
;
 Diastereoselective Pictet-Spengler Based Synthesis of a Chiral
 Tetrahydroisoquinoline D1 Potentiator.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00177
_journal_year                    2020
_chemical_formula_moiety         'C12 H12 Br N O2'
_chemical_formula_sum            'C12 H12 Br N O2'
_chemical_formula_weight         282.14
_chemical_name_systematic        LSN3179159
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 112.7990(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.5606(6)
_cell_length_b                   8.3186(3)
_cell_length_c                   19.5153(7)
_cell_measurement_reflns_used    9449
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      78.15
_cell_measurement_theta_min      2.46
_cell_volume                     2328.74(15)
_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 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            84492
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        66.993
_diffrn_reflns_theta_max         66.993
_diffrn_reflns_theta_min         2.456
_exptl_absorpt_coefficient_mu    4.695
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_correction_T_min  0.3794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.609
_exptl_crystal_description       rods
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.988
_refine_diff_density_min         -1.512
_refine_diff_density_rms         0.102
_refine_ls_abs_structure_details
;
 Flack x determined using 3454 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.116(5)
_refine_ls_extinction_coef       0.0078(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.641
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     582
_refine_ls_number_reflns         8122
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.642
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0554
_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)+(0.1000P)²+0.1373P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1851
_refine_ls_wR_factor_ref         0.1874
_reflns_Friedel_coverage         0.823
_reflns_Friedel_fraction_full    0.957
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                7897
_reflns_number_total             8122
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00177_si_002.cif
_cod_data_source_block           compound_10
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4038429
_elnb_number
;
EL19500-002
;
_lot_number
;
RP7-H81735-006
;
_comments
;
This is the second daset collected for this crystal at room temperature.
The data quality is good than the previous dataset 18013. 
The structure is solved with 0.0595 R factor and absolute stereochemistry
is determined.
;
_shelx_shelxl_version_number     2017/1
_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   0.138
_shelx_estimated_absorpt_t_max   0.651
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
Br4 Br 1.13657(6) 0.25412(12) 0.36294(4) 0.0740(3) Uani 1 1 d . . . . .
Br2 Br 0.64618(10) 0.35690(18) 0.87485(6) 0.1104(5) Uani 1 1 d . . . . .
Br3 Br 0.70005(8) 0.9682(2) 0.74148(7) 0.1088(5) Uani 1 1 d . . . . .
Br1 Br 0.86046(19) 0.3554(2) 0.79978(13) 0.1609(10) Uani 1 1 d . . . . .
C42 C 0.9896(4) 0.2347(7) 0.2184(3) 0.0467(11) Uani 1 1 d . . . . .
C13 C 0.5210(6) 0.3637(9) 0.8039(4) 0.0622(16) Uani 1 1 d . . . . .
C17 C 0.4115(4) 0.4233(7) 0.6821(3) 0.0473(12) Uani 1 1 d . . . . .
C37 C 1.0133(5) 0.2078(8) 0.2935(4) 0.0559(14) Uani 1 1 d . . . . .
C18 C 0.5046(5) 0.4104(7) 0.7314(3) 0.0516(13) Uani 1 1 d . . . . .
N2 N 0.4631(4) 0.5260(8) 0.5887(3) 0.0609(13) Uani 1 1 d . . . . .
C40 C 0.8338(5) 0.1478(10) 0.2001(5) 0.0691(19) Uani 1 1 d . . . . .
H40 H 0.773106 0.123467 0.168307 0.083 Uiso 1 1 calc R U . . .
C44 C 1.0302(4) 0.2609(10) 0.1070(3) 0.0555(13) Uani 1 1 d . . . . .
H44 H 1.037987 0.146341 0.099278 0.067 Uiso 1 1 calc R U . . .
C45 C 0.8602(4) 0.2401(10) 0.0878(4) 0.0601(15) Uani 1 1 d . . . . .
H45 H 0.811148 0.321520 0.076842 0.072 Uiso 1 1 calc R U . . .
C22 C 0.3281(6) 0.3449(14) 0.5461(5) 0.081(2) Uani 1 1 d . . . . .
H22A H 0.314016 0.382843 0.496442 0.122 Uiso 1 1 calc R U . . .
H22B H 0.271206 0.321727 0.552382 0.122 Uiso 1 1 calc R U . . .
H22C H 0.365139 0.248989 0.554492 0.122 Uiso 1 1 calc R U . . .
N4 N 0.9335(4) 0.3091(8) 0.0686(4) 0.0638(15) Uani 1 1 d . . . . .
C21 C 0.3825(5) 0.4743(8) 0.6018(4) 0.0550(14) Uani 1 1 d . . . . .
H21 H 0.341301 0.567556 0.594020 0.066 Uiso 1 1 calc R U . . .
C43 C 1.0600(4) 0.2976(8) 0.1888(3) 0.0503(13) Uani 1 1 d . . . . .
H43A H 1.066561 0.412882 0.196390 0.060 Uiso 1 1 calc R U . . .
H43B H 1.120217 0.248608 0.216124 0.060 Uiso 1 1 calc R U . . .
C41 C 0.8963(4) 0.2061(8) 0.1709(4) 0.0536(14) Uani 1 1 d . . . . .
C16 C 0.3406(6) 0.3881(10) 0.7067(5) 0.0687(18) Uani 1 1 d . . . . .
H16 H 0.278846 0.394162 0.673279 0.082 Uiso 1 1 calc R U . . .
C46 C 0.8171(6) 0.0952(14) 0.0388(6) 0.084(2) Uani 1 1 d . . . . .
H46A H 0.802984 0.122305 -0.012240 0.127 Uiso 1 1 calc R U . . .
H46B H 0.760883 0.064752 0.044705 0.127 Uiso 1 1 calc R U . . .
H46C H 0.860386 0.007154 0.053071 0.127 Uiso 1 1 calc R U . . .
C32 C 0.5814(5) 0.8408(9) 0.9182(3) 0.0598(15) Uani 1 1 d . . . . .
H32 H 0.567246 0.950000 0.929557 0.072 Uiso 1 1 calc R U . . .
C30 C 0.5495(4) 0.8755(8) 0.7842(3) 0.0490(12) Uani 1 1 d . . . . .
C31 C 0.6233(5) 0.8450(10) 0.8605(3) 0.0583(15) Uani 1 1 d . . . . .
H31A H 0.653809 0.743353 0.860559 0.070 Uiso 1 1 calc R U . . .
H31B H 0.669979 0.929228 0.872756 0.070 Uiso 1 1 calc R U . . .
C27 C 0.4172(8) 0.9264(13) 0.6393(5) 0.090(3) Uani 1 1 d . . . . .
H27 H 0.372151 0.942376 0.591816 0.108 Uiso 1 1 calc R U . . .
N3 N 0.4979(5) 0.7443(8) 0.8913(3) 0.0652(14) Uani 1 1 d . . . . .
C28 C 0.3919(6) 0.8726(11) 0.6957(4) 0.075(2) Uani 1 1 d . . . . .
H28 H 0.329275 0.852262 0.684962 0.090 Uiso 1 1 calc R U . . .
C25 C 0.5744(5) 0.9309(9) 0.7256(4) 0.0580(15) Uani 1 1 d . . . . .
C29 C 0.4556(4) 0.8474(7) 0.7676(4) 0.0524(13) Uani 1 1 d . . . . .
O8 O 0.8522(5) 0.5006(10) -0.0146(4) 0.095(2) Uani 1 1 d . . . . .
O7 O 1.0055(4) 0.4678(9) 0.0187(3) 0.0807(16) Uani 1 1 d . . . . .
C48 C 1.0758(6) 0.3633(14) 0.0664(5) 0.076(2) Uani 1 1 d . . . . .
H48A H 1.126672 0.425160 0.101471 0.091 Uiso 1 1 calc R U . . .
H48B H 1.100261 0.296001 0.037555 0.091 Uiso 1 1 calc R U . . .
C47 C 0.9219(6) 0.4289(11) 0.0211(4) 0.0678(18) Uani 1 1 d . . . . .
C38 C 0.9511(6) 0.1546(10) 0.3232(5) 0.0673(18) Uani 1 1 d . . . . .
H38 H 0.969528 0.138584 0.374094 0.081 Uiso 1 1 calc R U . . .
C34 C 0.3592(7) 0.9182(12) 0.8399(7) 0.087(3) Uani 1 1 d . . . . .
H34A H 0.329067 0.873453 0.870180 0.130 Uiso 1 1 calc R U . . .
H34B H 0.312941 0.954650 0.793681 0.130 Uiso 1 1 calc R U . . .
H34C H 0.397518 1.007257 0.865477 0.130 Uiso 1 1 calc R U . . .
O6 O 0.4139(8) 0.5892(10) 0.9425(5) 0.111(3) Uani 1 1 d . . . . .
O5 O 0.5677(8) 0.6639(9) 1.0068(4) 0.105(3) Uani 1 1 d . . . . .
C33 C 0.4195(5) 0.7908(8) 0.8249(4) 0.0573(15) Uani 1 1 d . . . . .
H33 H 0.380824 0.695392 0.805273 0.069 Uiso 1 1 calc R U . . .
C35 C 0.4869(9) 0.6594(11) 0.9456(5) 0.080(2) Uani 1 1 d . . . . .
C26 C 0.5098(7) 0.9562(11) 0.6541(4) 0.075(2) Uani 1 1 d . . . . .
H26 H 0.528499 0.992423 0.616938 0.090 Uiso 1 1 calc R U . . .
C36 C 0.6356(8) 0.7494(13) 0.9898(4) 0.086(2) Uani 1 1 d . . . . .
H36A H 0.679752 0.675907 0.982603 0.103 Uiso 1 1 calc R U . . .
H36B H 0.669290 0.823322 1.029596 0.103 Uiso 1 1 calc R U . . .
C19 C 0.5823(4) 0.4531(10) 0.7067(4) 0.0612(15) Uani 1 1 d . . . . .
H19A H 0.603267 0.561845 0.722467 0.073 Uiso 1 1 calc R U . . .
H19B H 0.634550 0.381148 0.730334 0.073 Uiso 1 1 calc R U . . .
C20 C 0.5515(5) 0.4413(10) 0.6235(4) 0.0606(15) Uani 1 1 d . . . . .
H20 H 0.545519 0.328725 0.607509 0.073 Uiso 1 1 calc R U . . .
C24 C 0.6092(7) 0.5382(15) 0.5889(6) 0.090(3) Uani 1 1 d . . . . .
H24A H 0.650213 0.613085 0.624818 0.108 Uiso 1 1 calc R U . . .
H24B H 0.646658 0.466697 0.572495 0.108 Uiso 1 1 calc R U . . .
O3 O 0.5427(6) 0.6232(11) 0.5267(4) 0.103(2) Uani 1 1 d . . . . .
C23 C 0.4586(7) 0.6146(12) 0.5301(4) 0.077(2) Uani 1 1 d . . . . .
O4 O 0.3903(7) 0.6834(11) 0.4856(4) 0.108(3) Uani 1 1 d . . . . .
C14 C 0.4513(9) 0.3315(10) 0.8285(5) 0.084(3) Uani 1 1 d . . . . .
H14 H 0.465640 0.301353 0.877560 0.100 Uiso 1 1 calc R U . . .
C6 C 0.9575(5) 0.2259(9) 0.7133(4) 0.0618(16) Uani 1 1 d . . . . .
C7 C 0.8720(5) 0.2696(12) 0.6458(5) 0.0706(18) Uani 1 1 d . . . . .
H7A H 0.825663 0.185199 0.635556 0.085 Uiso 1 1 calc R U . . .
H7B H 0.845190 0.368439 0.655065 0.085 Uiso 1 1 calc R U . . .
C1 C 0.9616(9) 0.2642(12) 0.7839(5) 0.090(3) Uani 1 1 d . U . . .
C2 C 1.0503(18) 0.212(2) 0.8470(6) 0.174(11) Uani 1 1 d . U . . .
H2 H 1.051264 0.219006 0.894891 0.209 Uiso 1 1 calc R U . . .
C15 C 0.3599(8) 0.3441(11) 0.7797(6) 0.084(3) Uani 1 1 d . . . . .
H15 H 0.311752 0.323582 0.795517 0.100 Uiso 1 1 calc R U . . .
C39 C 0.8603(6) 0.1259(12) 0.2747(6) 0.079(2) Uani 1 1 d . . . . .
H39 H 0.816689 0.091132 0.293224 0.095 Uiso 1 1 calc R U . . .
N1 N 0.9469(6) 0.1488(10) 0.5734(4) 0.0784(19) Uani 1 1 d . . . . .
C9 C 1.0317(7) 0.0990(10) 0.6299(7) 0.083(3) Uani 1 1 d . . . . .
H9 H 1.034720 -0.018565 0.628430 0.099 Uiso 1 1 calc R U . . .
C5 C 1.0326(5) 0.1474(9) 0.7057(5) 0.074(2) Uani 1 1 d . . . . .
O1 O 0.8350(10) 0.177(2) 0.4598(5) 0.168(7) Uani 1 1 d . . . . .
C8 C 0.8985(5) 0.2910(11) 0.5804(5) 0.073(2) Uani 1 1 d . . . . .
H8 H 0.938724 0.385464 0.587556 0.088 Uiso 1 1 calc R U . . .
C11 C 0.9095(13) 0.092(2) 0.5007(9) 0.126(6) Uani 1 1 d . . . . .
C12 C 0.8165(8) 0.299(2) 0.5036(8) 0.136(7) Uani 1 1 d . . . . .
H12A H 0.757712 0.279156 0.508489 0.163 Uiso 1 1 calc R U . . .
H12B H 0.813784 0.403971 0.481071 0.163 Uiso 1 1 calc R U . . .
C10 C 1.1180(10) 0.1678(19) 0.6189(11) 0.135(6) Uani 1 1 d . . . . .
H10A H 1.118359 0.130490 0.572505 0.203 Uiso 1 1 calc R U . . .
H10B H 1.173741 0.132463 0.658863 0.203 Uiso 1 1 calc R U . . .
H10C H 1.115441 0.283128 0.618668 0.203 Uiso 1 1 calc R U . . .
O2 O 0.9463(15) -0.0209(19) 0.4811(9) 0.220(10) Uani 1 1 d . . . . .
C4 C 1.1109(9) 0.1125(18) 0.7686(10) 0.134(7) Uani 1 1 d . . . . .
H4 H 1.159353 0.055069 0.763497 0.161 Uiso 1 1 calc R U . . .
C3 C 1.1197(17) 0.162(3) 0.8411(12) 0.175(11) Uani 1 1 d . U . . .
H3 H 1.176220 0.155826 0.881754 0.210 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 0.0181 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'
Br Br -0.6763 1.2805 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C37 C42 C41 117.0(5) . . ?
C37 C42 C43 121.6(5) . . ?
C41 C42 C43 121.3(5) . . ?
C14 C13 C18 123.4(8) . . ?
C14 C13 Br2 117.7(6) . . ?
C18 C13 Br2 118.7(6) . . ?
C16 C17 C18 119.6(7) . . ?
C16 C17 C21 117.1(6) . . ?
C18 C17 C21 123.3(5) . . ?
C38 C37 C42 123.7(6) . . ?
C38 C37 Br4 116.2(5) . . ?
C42 C37 Br4 120.1(5) . . ?
C13 C18 C17 117.0(6) . . ?
C13 C18 C19 122.4(7) . . ?
C17 C18 C19 120.5(6) . . ?
C23 N2 C21 123.8(7) . . ?
C23 N2 C20 113.1(6) . . ?
C21 N2 C20 120.1(6) . . ?
C39 C40 C41 121.0(8) . . ?
C39 C40 H40 119.5 . . ?
C41 C40 H40 119.5 . . ?
N4 C44 C43 108.8(5) . . ?
N4 C44 C48 100.1(6) . . ?
C43 C44 C48 115.2(6) . . ?
N4 C44 H44 110.7 . . ?
C43 C44 H44 110.7 . . ?
C48 C44 H44 110.7 . . ?
N4 C45 C46 110.5(7) . . ?
N4 C45 C41 110.2(5) . . ?
C46 C45 C41 114.4(7) . . ?
N4 C45 H45 107.1 . . ?
C46 C45 H45 107.1 . . ?
C41 C45 H45 107.1 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C47 N4 C45 124.8(6) . . ?
C47 N4 C44 113.6(6) . . ?
C45 N4 C44 121.3(6) . . ?
N2 C21 C17 109.7(5) . . ?
N2 C21 C22 111.3(6) . . ?
C17 C21 C22 113.6(6) . . ?
N2 C21 H21 107.4 . . ?
C17 C21 H21 107.4 . . ?
C22 C21 H21 107.4 . . ?
C44 C43 C42 111.2(5) . . ?
C44 C43 H43A 109.4 . . ?
C42 C43 H43A 109.4 . . ?
C44 C43 H43B 109.4 . . ?
C42 C43 H43B 109.4 . . ?
H43A C43 H43B 108.0 . . ?
C40 C41 C42 119.6(7) . . ?
C40 C41 C45 118.3(6) . . ?
C42 C41 C45 122.1(5) . . ?
C15 C16 C17 121.6(9) . . ?
C15 C16 H16 119.2 . . ?
C17 C16 H16 119.2 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
N3 C32 C31 109.4(6) . . ?
N3 C32 C36 99.0(7) . . ?
C31 C32 C36 116.8(7) . . ?
N3 C32 H32 110.4 . . ?
C31 C32 H32 110.4 . . ?
C36 C32 H32 110.4 . . ?
C29 C30 C25 117.2(6) . . ?
C29 C30 C31 122.1(6) . . ?
C25 C30 C31 120.7(6) . . ?
C32 C31 C30 111.0(6) . . ?
C32 C31 H31A 109.4 . . ?
C30 C31 H31A 109.4 . . ?
C32 C31 H31B 109.4 . . ?
C30 C31 H31B 109.4 . . ?
H31A C31 H31B 108.0 . . ?
C28 C27 C26 119.3(8) . . ?
C28 C27 H27 120.3 . . ?
C26 C27 H27 120.3 . . ?
C35 N3 C32 112.3(7) . . ?
C35 N3 C33 121.9(7) . . ?
C32 N3 C33 120.3(6) . . ?
C27 C28 C29 123.0(8) . . ?
C27 C28 H28 118.5 . . ?
C29 C28 H28 118.5 . . ?
C26 C25 C30 123.0(7) . . ?
C26 C25 Br3 116.3(6) . . ?
C30 C25 Br3 120.7(5) . . ?
C28 C29 C30 119.1(7) . . ?
C28 C29 C33 118.2(6) . . ?
C30 C29 C33 122.7(6) . . ?
C47 O7 C48 109.6(6) . . ?
O7 C48 C44 106.8(6) . . ?
O7 C48 H48A 110.4 . . ?
C44 C48 H48A 110.4 . . ?
O7 C48 H48B 110.4 . . ?
C44 C48 H48B 110.4 . . ?
H48A C48 H48B 108.6 . . ?
O8 C47 N4 128.9(8) . . ?
O8 C47 O7 121.7(8) . . ?
N4 C47 O7 109.3(7) . . ?
C37 C38 C39 117.7(7) . . ?
C37 C38 H38 121.2 . . ?
C39 C38 H38 121.2 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C35 O5 C36 109.2(6) . . ?
N3 C33 C29 108.7(5) . . ?
N3 C33 C34 112.6(7) . . ?
C29 C33 C34 111.2(7) . . ?
N3 C33 H33 108.1 . . ?
C29 C33 H33 108.1 . . ?
C34 C33 H33 108.1 . . ?
O6 C35 N3 126.7(11) . . ?
O6 C35 O5 124.5(8) . . ?
N3 C35 O5 108.8(9) . . ?
C27 C26 C25 118.4(8) . . ?
C27 C26 H26 120.8 . . ?
C25 C26 H26 120.8 . . ?
O5 C36 C32 105.5(8) . . ?
O5 C36 H36A 110.6 . . ?
C32 C36 H36A 110.6 . . ?
O5 C36 H36B 110.6 . . ?
C32 C36 H36B 110.6 . . ?
H36A C36 H36B 108.8 . . ?
C20 C19 C18 111.6(5) . . ?
C20 C19 H19A 109.3 . . ?
C18 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
C18 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
N2 C20 C19 108.7(5) . . ?
N2 C20 C24 98.5(7) . . ?
C19 C20 C24 116.1(7) . . ?
N2 C20 H20 111.0 . . ?
C19 C20 H20 111.0 . . ?
C24 C20 H20 111.0 . . ?
O3 C24 C20 106.1(7) . . ?
O3 C24 H24A 110.5 . . ?
C20 C24 H24A 110.5 . . ?
O3 C24 H24B 110.5 . . ?
C20 C24 H24B 110.5 . . ?
H24A C24 H24B 108.7 . . ?
C23 O3 C24 109.2(6) . . ?
O4 C23 O3 122.5(8) . . ?
O4 C23 N2 127.4(9) . . ?
O3 C23 N2 110.1(9) . . ?
C13 C14 C15 119.3(8) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C1 C6 C5 119.6(9) . . ?
C1 C6 C7 119.7(9) . . ?
C5 C6 C7 120.7(7) . . ?
C8 C7 C6 109.4(6) . . ?
C8 C7 H7A 109.8 . . ?
C6 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
C6 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
C6 C1 C2 114.6(14) . . ?
C6 C1 Br1 122.4(8) . . ?
C2 C1 Br1 122.7(11) . . ?
C3 C2 C1 126.2(17) . . ?
C3 C2 H2 116.9 . . ?
C1 C2 H2 116.9 . . ?
C14 C15 C16 119.1(8) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C40 C39 C38 120.9(7) . . ?
C40 C39 H39 119.5 . . ?
C38 C39 H39 119.5 . . ?
C11 N1 C9 126.3(12) . . ?
C11 N1 C8 110.4(12) . . ?
C9 N1 C8 122.1(7) . . ?
N1 C9 C5 109.5(7) . . ?
N1 C9 C10 112.3(10) . . ?
C5 C9 C10 110.7(11) . . ?
N1 C9 H9 108.1 . . ?
C5 C9 H9 108.1 . . ?
C10 C9 H9 108.1 . . ?
C4 C5 C6 119.3(13) . . ?
C4 C5 C9 118.5(12) . . ?
C6 C5 C9 122.2(7) . . ?
C11 O1 C12 110.5(9) . . ?
N1 C8 C7 108.1(7) . . ?
N1 C8 C12 102.1(11) . . ?
C7 C8 C12 115.7(9) . . ?
N1 C8 H8 110.2 . . ?
C7 C8 H8 110.2 . . ?
C12 C8 H8 110.2 . . ?
O2 C11 O1 128.2(17) . . ?
O2 C11 N1 121(2) . . ?
O1 C11 N1 110.9(14) . . ?
O1 C12 C8 105.4(13) . . ?
O1 C12 H12A 110.7 . . ?
C8 C12 H12A 110.7 . . ?
O1 C12 H12B 110.7 . . ?
C8 C12 H12B 110.7 . . ?
H12A C12 H12B 108.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C4 C3 122.1(17) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C2 C3 C4 116.7(18) . . ?
C2 C3 H3 121.6 . . ?
C4 C3 H3 121.6 . . ?
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
Br4 C37 1.910(7) . ?
Br2 C13 1.904(8) . ?
Br3 C25 1.884(7) . ?
Br1 C1 1.877(14) . ?
C42 C37 1.383(9) . ?
C42 C41 1.409(9) . ?
C42 C43 1.516(8) . ?
C13 C14 1.371(13) . ?
C13 C18 1.393(9) . ?
C17 C16 1.395(9) . ?
C17 C18 1.397(10) . ?
C17 C21 1.512(9) . ?
C37 C38 1.381(11) . ?
C18 C19 1.508(9) . ?
N2 C23 1.339(10) . ?
N2 C21 1.439(9) . ?
N2 C20 1.458(10) . ?
C40 C39 1.362(14) . ?
C40 C41 1.391(10) . ?
C40 H40 0.9300 . ?
C44 N4 1.453(8) . ?
C44 C43 1.510(8) . ?
C44 C48 1.515(10) . ?
C44 H44 0.9800 . ?
C45 N4 1.449(10) . ?
C45 C46 1.523(12) . ?
C45 C41 1.523(10) . ?
C45 H45 0.9800 . ?
C22 C21 1.531(11) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N4 C47 1.326(10) . ?
C21 H21 0.9800 . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C16 C15 1.388(14) . ?
C16 H16 0.9300 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C32 N3 1.443(10) . ?
C32 C31 1.504(10) . ?
C32 C36 1.526(10) . ?
C32 H32 0.9800 . ?
C30 C29 1.388(9) . ?
C30 C25 1.418(9) . ?
C30 C31 1.509(8) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C27 C28 1.378(14) . ?
C27 C26 1.379(16) . ?
C27 H27 0.9300 . ?
N3 C35 1.337(10) . ?
N3 C33 1.446(10) . ?
C28 C29 1.384(10) . ?
C28 H28 0.9300 . ?
C25 C26 1.383(11) . ?
C29 C33 1.509(10) . ?
O8 C47 1.196(11) . ?
O7 C47 1.358(10) . ?
O7 C48 1.424(11) . ?
C48 H48A 0.9700 . ?
C48 H48B 0.9700 . ?
C38 C39 1.383(14) . ?
C38 H38 0.9300 . ?
C34 C33 1.517(11) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
O6 C35 1.258(14) . ?
O5 C35 1.359(15) . ?
O5 C36 1.414(15) . ?
C33 H33 0.9800 . ?
C26 H26 0.9300 . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C19 C20 1.507(10) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C24 1.544(11) . ?
C20 H20 0.9800 . ?
C24 O3 1.439(16) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
O3 C23 1.338(13) . ?
C23 O4 1.223(14) . ?
C14 C15 1.374(16) . ?
C14 H14 0.9300 . ?
C6 C1 1.393(11) . ?
C6 C5 1.396(13) . ?
C6 C7 1.509(11) . ?
C7 C8 1.497(12) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C1 C2 1.52(3) . ?
C2 C3 1.20(3) . ?
C2 H2 0.9300 . ?
C15 H15 0.9300 . ?
C39 H39 0.9300 . ?
N1 C11 1.390(14) . ?
N1 C9 1.414(14) . ?
N1 C8 1.437(13) . ?
C9 C5 1.527(15) . ?
C9 C10 1.550(14) . ?
C9 H9 0.9800 . ?
C5 C4 1.385(15) . ?
O1 C11 1.33(3) . ?
O1 C12 1.43(3) . ?
C8 C12 1.548(13) . ?
C8 H8 0.9800 . ?
C11 O2 1.24(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C4 C3 1.43(3) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
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
_geom_hbond_publ_flag
C10 H10C O2 0.96 2.43 3.164(19) 132.6 2_756 yes
C12 H12A O4 0.97 2.48 3.443(16) 170.8 2_646 yes
C24 H24B O4 0.97 2.58 3.291(14) 130.1 2_646 yes
C38 H38 O2 0.93 2.61 3.436(17) 147.6 . yes
C48 H48B O8 0.97 2.65 3.502(14) 146.1 2_745 yes
C44 H44 O7 0.98 2.60 3.349(9) 133.4 2_745 yes
C44 H44 Br1 0.98 3.13 3.897(8) 135.8 2_746 yes
C10 H10C O2 0.96 2.43 3.164(19) 132.6 2_756 yes
C12 H12A O4 0.97 2.48 3.443(16) 170.8 2_646 yes
C24 H24B O4 0.97 2.58 3.291(14) 130.1 2_646 yes
C34 H34C O5 0.96 2.68 3.432(12) 136.0 2_657 yes
C38 H38 O2 0.93 2.61 3.436(17) 147.6 . yes
C48 H48B O8 0.97 2.65 3.502(14) 146.1 2_745 yes
C32 H32 O6 0.98 2.66 3.393(10) 131.5 2_657 yes
C22 H22A Br4 0.96 3.16 3.738(8) 120.4 1_455 yes
C44 H44 O7 0.98 2.60 3.349(9) 133.4 2_745 yes
C44 H44 Br1 0.98 3.13 3.897(8) 135.8 2_746 yes
C10 H10C O2 0.96 2.43 3.164(19) 132.6 2_756 yes
C12 H12A O4 0.97 2.48 3.443(16) 170.8 2_646 yes
C24 H24B O4 0.97 2.58 3.291(14) 130.1 2_646 yes
C38 H38 O2 0.93 2.61 3.436(17) 147.6 . yes
C48 H48B O8 0.97 2.65 3.502(14) 146.1 2_745 yes
C22 H22A Br4 0.96 3.16 3.738(8) 120.4 1_455 yes
C44 H44 O7 0.98 2.60 3.349(9) 133.4 2_745 yes
C44 H44 Br1 0.98 3.13 3.897(8) 135.8 2_746 yes
C10 H10C O2 0.96 2.43 3.164(19) 132.6 2_756 yes
C12 H12A O4 0.97 2.48 3.443(16) 170.8 2_646 yes
C24 H24B O4 0.97 2.58 3.291(14) 130.1 2_646 yes
C38 H38 O2 0.93 2.61 3.436(17) 147.6 . yes
C48 H48B O8 0.97 2.65 3.502(14) 146.1 2_745 yes
C22 H22A Br4 0.96 3.16 3.738(8) 120.4 1_455 yes
C44 H44 O7 0.98 2.60 3.349(9) 133.4 2_745 yes
C44 H44 Br1 0.98 3.13 3.897(8) 135.8 2_746 yes
C44 H44 Br1 0.98 3.13 3.897(8) 135.8 2_746 yes
C44 H44 O7 0.98 2.60 3.349(9) 133.4 2_745 yes
C22 H22A Br4 0.96 3.16 3.738(8) 120.4 1_455 yes
C32 H32 O6 0.98 2.66 3.393(10) 131.5 2_657 yes
C48 H48B O8 0.97 2.65 3.502(14) 146.1 2_745 yes
C38 H38 O2 0.93 2.61 3.436(17) 147.6 . yes
C34 H34C O5 0.96 2.68 3.432(12) 136.0 2_657 yes
C24 H24B O4 0.97 2.58 3.291(14) 130.1 2_646 yes
C12 H12A O4 0.97 2.48 3.443(16) 170.8 2_646 yes
C10 H10C O2 0.96 2.43 3.164(19) 132.6 2_756 yes
C44 H44 Br1 0.98 3.13 3.897(8) 135.8 2_746 yes
C44 H44 O7 0.98 2.60 3.349(9) 133.4 2_745 yes
C48 H48B O8 0.97 2.65 3.502(14) 146.1 2_745 yes
C38 H38 O2 0.93 2.61 3.436(17) 147.6 . yes
C24 H24B O4 0.97 2.58 3.291(14) 130.1 2_646 yes
C12 H12A O4 0.97 2.48 3.443(16) 170.8 2_646 yes
C10 H10C O2 0.96 2.43 3.164(19) 132.6 2_756 yes
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
C41 C42 C37 C38 0.4(10) . . . . ?
C43 C42 C37 C38 178.3(7) . . . . ?
C41 C42 C37 Br4 -176.6(4) . . . . ?
C43 C42 C37 Br4 1.3(8) . . . . ?
C14 C13 C18 C17 -0.4(10) . . . . ?
Br2 C13 C18 C17 -176.3(4) . . . . ?
C14 C13 C18 C19 176.9(7) . . . . ?
Br2 C13 C18 C19 1.0(9) . . . . ?
C16 C17 C18 C13 -0.7(9) . . . . ?
C21 C17 C18 C13 179.3(6) . . . . ?
C16 C17 C18 C19 -178.0(6) . . . . ?
C21 C17 C18 C19 2.0(9) . . . . ?
C46 C45 N4 C47 93.6(9) . . . . ?
C41 C45 N4 C47 -139.0(7) . . . . ?
C46 C45 N4 C44 -92.8(8) . . . . ?
C41 C45 N4 C44 34.6(9) . . . . ?
C43 C44 N4 C47 114.6(7) . . . . ?
C48 C44 N4 C47 -6.6(9) . . . . ?
C43 C44 N4 C45 -59.6(9) . . . . ?
C48 C44 N4 C45 179.2(7) . . . . ?
C23 N2 C21 C17 -162.6(7) . . . . ?
C20 N2 C21 C17 38.6(8) . . . . ?
C23 N2 C21 C22 70.9(10) . . . . ?
C20 N2 C21 C22 -87.9(8) . . . . ?
C16 C17 C21 N2 172.4(6) . . . . ?
C18 C17 C21 N2 -7.5(8) . . . . ?
C16 C17 C21 C22 -62.4(8) . . . . ?
C18 C17 C21 C22 117.7(7) . . . . ?
N4 C44 C43 C42 48.8(7) . . . . ?
C48 C44 C43 C42 160.3(6) . . . . ?
C37 C42 C43 C44 159.5(6) . . . . ?
C41 C42 C43 C44 -22.7(8) . . . . ?
C39 C40 C41 C42 3.5(11) . . . . ?
C39 C40 C41 C45 -175.3(8) . . . . ?
C37 C42 C41 C40 -2.3(9) . . . . ?
C43 C42 C41 C40 179.8(6) . . . . ?
C37 C42 C41 C45 176.5(6) . . . . ?
C43 C42 C41 C45 -1.4(9) . . . . ?
N4 C45 C41 C40 176.4(6) . . . . ?
C46 C45 C41 C40 -58.3(9) . . . . ?
N4 C45 C41 C42 -2.4(9) . . . . ?
C46 C45 C41 C42 122.8(7) . . . . ?
C18 C17 C16 C15 1.6(10) . . . . ?
C21 C17 C16 C15 -178.3(7) . . . . ?
N3 C32 C31 C30 45.4(9) . . . . ?
C36 C32 C31 C30 156.7(7) . . . . ?
C29 C30 C31 C32 -20.3(10) . . . . ?
C25 C30 C31 C32 161.3(7) . . . . ?
C31 C32 N3 C35 143.8(7) . . . . ?
C36 C32 N3 C35 21.1(9) . . . . ?
C31 C32 N3 C33 -61.8(9) . . . . ?
C36 C32 N3 C33 175.5(7) . . . . ?
C26 C27 C28 C29 0.4(15) . . . . ?
C29 C30 C25 C26 -0.4(11) . . . . ?
C31 C30 C25 C26 178.0(8) . . . . ?
C29 C30 C25 Br3 -178.5(5) . . . . ?
C31 C30 C25 Br3 -0.1(9) . . . . ?
C27 C28 C29 C30 -0.7(13) . . . . ?
C27 C28 C29 C33 179.0(8) . . . . ?
C25 C30 C29 C28 0.7(10) . . . . ?
C31 C30 C29 C28 -177.7(7) . . . . ?
C25 C30 C29 C33 -179.0(6) . . . . ?
C31 C30 C29 C33 2.6(10) . . . . ?
C47 O7 C48 C44 -5.8(10) . . . . ?
N4 C44 C48 O7 7.1(9) . . . . ?
C43 C44 C48 O7 -109.4(7) . . . . ?
C45 N4 C47 O8 -0.6(14) . . . . ?
C44 N4 C47 O8 -174.6(9) . . . . ?
C45 N4 C47 O7 177.5(7) . . . . ?
C44 N4 C47 O7 3.5(9) . . . . ?
C48 O7 C47 O8 179.9(9) . . . . ?
C48 O7 C47 N4 1.7(10) . . . . ?
C42 C37 C38 C39 0.4(12) . . . . ?
Br4 C37 C38 C39 177.6(7) . . . . ?
C35 N3 C33 C29 -166.1(7) . . . . ?
C32 N3 C33 C29 42.0(8) . . . . ?
C35 N3 C33 C34 70.3(9) . . . . ?
C32 N3 C33 C34 -81.6(8) . . . . ?
C28 C29 C33 N3 169.5(7) . . . . ?
C30 C29 C33 N3 -10.8(8) . . . . ?
C28 C29 C33 C34 -66.0(9) . . . . ?
C30 C29 C33 C34 113.7(8) . . . . ?
C32 N3 C35 O6 165.7(9) . . . . ?
C33 N3 C35 O6 11.7(14) . . . . ?
C32 N3 C35 O5 -12.7(10) . . . . ?
C33 N3 C35 O5 -166.6(7) . . . . ?
C36 O5 C35 O6 178.5(9) . . . . ?
C36 O5 C35 N3 -3.1(11) . . . . ?
C28 C27 C26 C25 -0.1(15) . . . . ?
C30 C25 C26 C27 0.1(13) . . . . ?
Br3 C25 C26 C27 178.3(7) . . . . ?
C35 O5 C36 C32 16.2(10) . . . . ?
N3 C32 C36 O5 -21.5(8) . . . . ?
C31 C32 C36 O5 -138.7(8) . . . . ?
C13 C18 C19 C20 159.6(7) . . . . ?
C17 C18 C19 C20 -23.2(9) . . . . ?
C23 N2 C20 C19 138.0(7) . . . . ?
C21 N2 C20 C19 -61.1(8) . . . . ?
C23 N2 C20 C24 16.6(9) . . . . ?
C21 N2 C20 C24 177.6(7) . . . . ?
C18 C19 C20 N2 48.5(8) . . . . ?
C18 C19 C20 C24 158.3(8) . . . . ?
N2 C20 C24 O3 -16.5(9) . . . . ?
C19 C20 C24 O3 -132.2(8) . . . . ?
C20 C24 O3 C23 12.3(11) . . . . ?
C24 O3 C23 O4 176.6(10) . . . . ?
C24 O3 C23 N2 -1.9(11) . . . . ?
C21 N2 C23 O4 11.0(15) . . . . ?
C20 N2 C23 O4 171.2(10) . . . . ?
C21 N2 C23 O3 -170.6(7) . . . . ?
C20 N2 C23 O3 -10.4(10) . . . . ?
C18 C13 C14 C15 0.4(12) . . . . ?
Br2 C13 C14 C15 176.4(7) . . . . ?
C1 C6 C7 C8 153.2(8) . . . . ?
C5 C6 C7 C8 -26.8(10) . . . . ?
C5 C6 C1 C2 -0.8(11) . . . . ?
C7 C6 C1 C2 179.1(8) . . . . ?
C5 C6 C1 Br1 -175.2(6) . . . . ?
C7 C6 C1 Br1 4.7(10) . . . . ?
C6 C1 C2 C3 10(2) . . . . ?
Br1 C1 C2 C3 -175(2) . . . . ?
C13 C14 C15 C16 0.5(13) . . . . ?
C17 C16 C15 C14 -1.6(12) . . . . ?
C41 C40 C39 C38 -2.7(14) . . . . ?
C37 C38 C39 C40 0.7(13) . . . . ?
C11 N1 C9 C5 -162.0(8) . . . . ?
C8 N1 C9 C5 31.9(10) . . . . ?
C11 N1 C9 C10 74.6(14) . . . . ?
C8 N1 C9 C10 -91.6(12) . . . . ?
C1 C6 C5 C4 -1.6(12) . . . . ?
C7 C6 C5 C4 178.4(8) . . . . ?
C1 C6 C5 C9 178.7(7) . . . . ?
C7 C6 C5 C9 -1.3(11) . . . . ?
N1 C9 C5 C4 -178.6(8) . . . . ?
C10 C9 C5 C4 -54.2(12) . . . . ?
N1 C9 C5 C6 1.1(10) . . . . ?
C10 C9 C5 C6 125.5(9) . . . . ?
C11 N1 C8 C7 130.3(7) . . . . ?
C9 N1 C8 C7 -61.5(9) . . . . ?
C11 N1 C8 C12 7.8(10) . . . . ?
C9 N1 C8 C12 176.0(8) . . . . ?
C6 C7 C8 N1 53.3(9) . . . . ?
C6 C7 C8 C12 167.1(11) . . . . ?
C12 O1 C11 O2 -178.9(13) . . . . ?
C12 O1 C11 N1 -0.3(15) . . . . ?
C9 N1 C11 O2 6.0(17) . . . . ?
C8 N1 C11 O2 173.5(11) . . . . ?
C9 N1 C11 O1 -172.8(9) . . . . ?
C8 N1 C11 O1 -5.3(12) . . . . ?
C11 O1 C12 C8 5.1(15) . . . . ?
N1 C8 C12 O1 -7.7(12) . . . . ?
C7 C8 C12 O1 -124.9(11) . . . . ?
C6 C5 C4 C3 -3.5(18) . . . . ?
C9 C5 C4 C3 176.3(14) . . . . ?
C1 C2 C3 C4 -15(3) . . . . ?
C5 C4 C3 C2 12(3) . . . . ?
