#------------------------------------------------------------------------------
#$Date: 2021-12-07 05:55:27 +0200 (Tue, 07 Dec 2021) $
#$Revision: 271227 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158373.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_7158373
loop_
_publ_author_name
'Milyutin, Constantine V.'
'Galimova, Renata D.'
'Komogortsev, Andrey N.'
'Lichitskii, Boris V.'
'Melekhina, Valeriya G.'
'Migulin, Vasily A.'
'Fakhrutdinov, Artem N.'
'Minyaev, Mikhail E.'
_publ_section_title
;
 Photoinduced assembly of the
 3,4,4a,7a-tetrahydro-1H-cyclopenta[b]pyridine-2,7-dione
 core on the basis of allomaltol derivatives.
;
_journal_issue                   45
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9975
_journal_page_last               9985
_journal_paper_doi               10.1039/d1ob01871j
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C15 H14 Br N O4'
_chemical_formula_sum            'C15 H14 Br N O4'
_chemical_formula_weight         352.18
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-07-27
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-09-20 deposited with the CCDC.	2021-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.1997(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.70863(6)
_cell_length_b                   31.0104(3)
_cell_length_c                   6.93722(7)
_cell_measurement_reflns_used    13015
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      78.7000
_cell_measurement_theta_min      2.8420
_cell_volume                     1354.44(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.106a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution
'SHELXT, SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    103.00 175.90   0.30    0.50    --  111.50  45.00  90.00  243
  2  ω    101.00 170.90   0.30    0.50    --  111.50  45.00 -30.00  233
  3  ω    146.00 176.00   0.30    0.50    --  111.50  45.00 -60.00  100
  4  ω    112.00 142.00   0.30    0.50    --  111.50  45.00 -60.00  100
  5  ω    107.00 140.00   0.30    0.50    --  111.50  45.00 -90.00  110
  6  ω    -26.00  25.00   0.30    0.50    --  -48.76  19.00  90.00  170
  7  ω    -26.00  25.00   0.30    0.50    --  -48.76  19.00 -30.00  170
  8  ω    -51.00 -18.00   0.30    0.50    --  -90.00  45.00 -60.00  110
  9  ω    -51.00 -18.00   0.30    0.50    --  -90.00  45.00 -90.00  110
 10  ω    -26.00  25.00   0.30    0.50    --  -48.76  19.00-180.00  170
 11  ω     45.00 106.20   0.30    0.50    --   48.76-144.00-107.00  204
 12  ω     45.00 124.20   0.30    0.50    --  111.50-144.00-107.00  264
 13  ω     43.00  92.20   0.30    0.50    --  111.50-138.00 -50.92  164
 14  ω     40.00 112.00   0.30    0.50    --  111.50-127.00  60.00  240
 15  ω     41.00  66.20   0.30    0.50    --  111.50-110.00  92.30   84
 16  ω     82.00 107.20   0.30    0.50    --  111.50-110.00  92.30   84
 17  ω     78.00 105.00   0.30    0.50    --  111.50-125.00  90.00   90
 18  ω     79.00 104.80   0.30    0.50    --  111.50-104.00 125.59   86
 19  ω     61.00 107.20   0.30    0.50    --  111.50-110.00 106.58  154
 20  ω     41.00 103.10   0.30    0.50    --  111.50 -95.00 120.00  207
 21  ω     55.00 106.00   0.30    0.50    --  111.50-106.00 167.12  170
 22  ω     36.00  96.00   0.30    0.50    --   48.76-127.00  60.00  200
 23  ω     76.00 104.20   0.30    0.50    --  111.50 -95.00  60.00   94
 24  ω     40.00  68.80   0.30    0.50    --  111.50 -95.00  60.00   96
 25  ω     40.00  65.20   0.30    0.50    --  111.50 -77.00  30.00   84
 26  ω     41.00  66.20   0.30    0.50    --  111.50 -61.00 120.00   84
 27  ω     42.00  69.00   0.30    0.50    --  111.50 -61.00 150.00   90
 28  ω     46.00  71.80   0.30    0.50    --  111.50 -77.00-180.00   86
 29  ω     41.00  69.20   0.30    0.50    --  111.50 -61.00-150.00   94
 30  ω     96.00 151.20   0.30    0.50    --  111.50 125.00 -30.00  184
 31  ω     82.00 169.00   0.30    0.50    --  111.50 144.00 -54.00  290
 32  ω     94.00 178.00   0.30    0.50    --  111.50 127.00 136.00  280
 33  ω    -88.00 -19.00   0.30    0.50    --  -90.00 127.00 136.00  230
 34  ω   -121.00 -73.00   0.30    0.50    --  -48.76-127.00  60.00  160
 35  ω   -141.00-115.80   0.30    0.50    --  -90.00-127.00  60.00   84
 36  ω   -121.00 -73.00   0.30    0.50    --  -48.76-125.00 -90.00  160
 37  ω   -121.00 -61.00   0.30    0.50    --  -48.76-144.00-107.00  200
 38  ω   -153.00 -60.00   0.30    0.50    --  -90.00-144.00-107.00  310
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1123936000
_diffrn_orient_matrix_UB_12      -0.0073935000
_diffrn_orient_matrix_UB_13      0.2319603000
_diffrn_orient_matrix_UB_21      0.0026654000
_diffrn_orient_matrix_UB_22      0.0490082000
_diffrn_orient_matrix_UB_23      0.0368014000
_diffrn_orient_matrix_UB_31      -0.2174472000
_diffrn_orient_matrix_UB_32      -0.0032375000
_diffrn_orient_matrix_UB_33      0.0284012000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            16633
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.301
_diffrn_reflns_theta_min         2.850
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.296
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.106a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.005
_exptl_crystal_size_min          0.004
_refine_diff_density_max         0.426
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         2906
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0247
_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)+(0.0384P)²+0.8365P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0681
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2758
_reflns_number_total             2906
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob01871j2.cif
_cod_data_source_block           9c
_cod_depositor_comments
'Adding full bibliography for 7158373--7158374.cif.'
_cod_original_cell_volume        1354.43(2)
_cod_database_code               7158373
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H13 Br N O4'
_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_max   0.983
_shelx_estimated_absorpt_t_min   0.725
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.321
_oxdiff_exptl_absorpt_empirical_full_min 0.853
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Br1 Br -0.00515(3) 0.22932(2) 0.21597(3) 0.01767(8) Uani 1 1 d . . . . .
N1 N 0.8364(2) 0.46085(5) 0.5834(2) 0.0125(3) Uani 1 1 d . . . . .
H1 H 0.900(4) 0.4847(9) 0.614(4) 0.028(6) Uiso 1 1 d . . . . .
C1 C 0.8283(2) 0.44316(5) 0.4051(2) 0.0124(3) Uani 1 1 d . . . . .
O1 O 0.91346(19) 0.46097(4) 0.29221(18) 0.0150(2) Uani 1 1 d . . . . .
C2 C 0.7148(3) 0.40070(5) 0.3468(3) 0.0136(3) Uani 1 1 d . . . . .
H2A H 0.824(4) 0.3779(7) 0.407(4) 0.019(5) Uiso 1 1 d . . . . .
H2B H 0.662(3) 0.3997(7) 0.196(3) 0.012(5) Uiso 1 1 d . . . . .
C3 C 0.5344(2) 0.39581(5) 0.4327(2) 0.0111(3) Uani 1 1 d . . . . .
H3 H 0.439(3) 0.4201(7) 0.384(3) 0.008(5) Uiso 1 1 d . . . . .
C4 C 0.6324(2) 0.39925(5) 0.6696(2) 0.0112(3) Uani 1 1 d . . . . .
O2 O 0.7670(2) 0.36332(4) 0.74602(19) 0.0159(2) Uani 1 1 d . . . . .
H2 H 0.863(4) 0.3733(9) 0.842(5) 0.034(7) Uiso 1 1 d . . . . .
C5 C 0.7549(2) 0.44255(5) 0.7324(2) 0.0110(3) Uani 1 1 d . . . . .
O3 O 0.93032(18) 0.43592(4) 0.91713(18) 0.0143(2) Uani 1 1 d . . . . .
H3A H 0.908(4) 0.4449(9) 1.016(4) 0.031(7) Uiso 1 1 d . . . . .
C6 C 0.5907(3) 0.47257(6) 0.7749(2) 0.0138(3) Uani 1 1 d . . . . .
O4 O 0.6054(2) 0.51164(4) 0.78027(19) 0.0186(3) Uani 1 1 d . . . . .
C7 C 0.4321(3) 0.44475(6) 0.8116(3) 0.0165(3) Uani 1 1 d . . . . .
H7 H 0.332(4) 0.4547(8) 0.862(4) 0.027(6) Uiso 1 1 d . . . . .
C8 C 0.4607(3) 0.40363(6) 0.7675(2) 0.0146(3) Uani 1 1 d . . . . .
C9 C 0.3474(3) 0.36526(7) 0.8065(3) 0.0218(4) Uani 1 1 d . . . . .
H9A H 0.265(5) 0.3511(11) 0.690(5) 0.054(9) Uiso 1 1 d . . . . .
H9B H 0.254(5) 0.3725(9) 0.876(5) 0.044(8) Uiso 1 1 d . . . . .
H9C H 0.446(5) 0.3461(10) 0.890(5) 0.052(9) Uiso 1 1 d . . . . .
C10 C 0.4063(3) 0.35493(5) 0.3608(2) 0.0117(3) Uani 1 1 d . . . . .
C11 C 0.5018(3) 0.31447(6) 0.3783(3) 0.0158(3) Uani 1 1 d . . . . .
H11 H 0.653(4) 0.3119(8) 0.426(4) 0.021(6) Uiso 1 1 d . . . . .
C12 C 0.3817(3) 0.27691(6) 0.3311(3) 0.0173(3) Uani 1 1 d . . . . .
H12 H 0.447(3) 0.2492(8) 0.348(3) 0.018(5) Uiso 1 1 d . . . . .
C13 C 0.1619(3) 0.28019(6) 0.2627(3) 0.0148(3) Uani 1 1 d . . . . .
C14 C 0.0616(3) 0.32001(6) 0.2316(3) 0.0136(3) Uani 1 1 d . . . . .
H14 H -0.079(3) 0.3222(7) 0.186(3) 0.009(5) Uiso 1 1 d . . . . .
C15 C 0.1849(3) 0.35714(5) 0.2815(2) 0.0132(3) Uani 1 1 d . . . . .
H15 H 0.122(3) 0.3848(8) 0.265(3) 0.019(5) 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 0.0181 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
C1 N1 H1 116.7(18) . . ?
C1 N1 C5 126.67(14) . . ?
C5 N1 H1 116.6(18) . . ?
N1 C1 C2 117.58(14) . . ?
O1 C1 N1 121.21(15) . . ?
O1 C1 C2 121.20(15) . . ?
C1 C2 H2A 106.1(13) . . ?
C1 C2 H2B 106.2(12) . . ?
C1 C2 C3 112.13(14) . . ?
H2A C2 H2B 111.6(18) . . ?
C3 C2 H2A 109.2(13) . . ?
C3 C2 H2B 111.5(12) . . ?
C2 C3 H3 107.6(12) . . ?
C2 C3 C4 107.70(13) . . ?
C4 C3 H3 107.5(12) . . ?
C10 C3 C2 112.93(13) . . ?
C10 C3 H3 107.8(12) . . ?
C10 C3 C4 113.02(13) . . ?
C3 C4 C5 110.25(13) . . ?
O2 C4 C3 108.95(13) . . ?
O2 C4 C5 111.53(13) . . ?
O2 C4 C8 112.54(13) . . ?
C8 C4 C3 111.62(13) . . ?
C8 C4 C5 101.81(13) . . ?
C4 O2 H2 103.4(19) . . ?
N1 C5 C4 115.67(13) . . ?
N1 C5 C6 111.79(13) . . ?
O3 C5 N1 107.53(13) . . ?
O3 C5 C4 108.68(13) . . ?
O3 C5 C6 109.72(13) . . ?
C6 C5 C4 103.34(12) . . ?
C5 O3 H3A 112.3(19) . . ?
O4 C6 C5 123.39(15) . . ?
O4 C6 C7 129.85(16) . . ?
C7 C6 C5 106.72(14) . . ?
C6 C7 H7 123.2(16) . . ?
C8 C7 C6 110.61(15) . . ?
C8 C7 H7 126.2(16) . . ?
C7 C8 C4 111.98(15) . . ?
C7 C8 C9 126.69(16) . . ?
C9 C8 C4 121.33(16) . . ?
C8 C9 H9A 114(2) . . ?
C8 C9 H9B 112.0(18) . . ?
C8 C9 H9C 109.1(19) . . ?
H9A C9 H9B 105(3) . . ?
H9A C9 H9C 109(3) . . ?
H9B C9 H9C 107(3) . . ?
C11 C10 C3 122.17(14) . . ?
C11 C10 C15 118.19(15) . . ?
C15 C10 C3 119.59(15) . . ?
C10 C11 H11 120.4(14) . . ?
C12 C11 C10 121.48(16) . . ?
C12 C11 H11 118.1(14) . . ?
C11 C12 H12 121.4(14) . . ?
C13 C12 C11 118.69(16) . . ?
C13 C12 H12 119.9(13) . . ?
C12 C13 Br1 119.52(14) . . ?
C14 C13 Br1 119.17(13) . . ?
C14 C13 C12 121.30(16) . . ?
C13 C14 H14 121.5(14) . . ?
C13 C14 C15 118.93(15) . . ?
C15 C14 H14 119.5(14) . . ?
C10 C15 H15 117.5(14) . . ?
C14 C15 C10 121.21(16) . . ?
C14 C15 H15 121.3(14) . . ?
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
Br1 C13 1.8971(17) . ?
N1 H1 0.84(3) . ?
N1 C1 1.337(2) . ?
N1 C5 1.442(2) . ?
C1 O1 1.246(2) . ?
C1 C2 1.505(2) . ?
C2 H2A 1.00(2) . ?
C2 H2B 0.98(2) . ?
C2 C3 1.530(2) . ?
C3 H3 0.97(2) . ?
C3 C4 1.549(2) . ?
C3 C10 1.516(2) . ?
C4 O2 1.4168(19) . ?
C4 C5 1.556(2) . ?
C4 C8 1.531(2) . ?
O2 H2 0.81(3) . ?
C5 O3 1.4240(19) . ?
C5 C6 1.546(2) . ?
O3 H3A 0.80(3) . ?
C6 O4 1.215(2) . ?
C6 C7 1.459(2) . ?
C7 H7 0.92(3) . ?
C7 C8 1.341(3) . ?
C8 C9 1.486(2) . ?
C9 H9A 0.92(4) . ?
C9 H9B 0.94(3) . ?
C9 H9C 0.93(3) . ?
C10 C11 1.395(2) . ?
C10 C15 1.396(2) . ?
C11 H11 0.96(2) . ?
C11 C12 1.389(2) . ?
C12 H12 0.96(2) . ?
C12 C13 1.388(2) . ?
C13 C14 1.387(2) . ?
C14 H14 0.89(2) . ?
C14 C15 1.390(2) . ?
C15 H15 0.94(2) . ?
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
N1 H1 O1 0.84(3) 2.06(3) 2.9047(19) 174(2) 3_766 yes
O2 H2 O3 0.81(3) 2.02(3) 2.6039(18) 128(3) . yes
O3 H3A O1 0.80(3) 1.97(3) 2.7550(17) 167(3) 1_556 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
Br1 C13 C14 C15 174.96(12) . . . . ?
N1 C1 C2 C3 30.3(2) . . . . ?
N1 C5 C6 O4 -36.7(2) . . . . ?
N1 C5 C6 C7 145.29(14) . . . . ?
C1 N1 C5 C4 -4.3(2) . . . . ?
C1 N1 C5 O3 117.28(17) . . . . ?
C1 N1 C5 C6 -122.24(17) . . . . ?
C1 C2 C3 C4 -59.35(17) . . . . ?
C1 C2 C3 C10 175.15(13) . . . . ?
O1 C1 C2 C3 -150.45(15) . . . . ?
C2 C3 C4 O2 -66.26(16) . . . . ?
C2 C3 C4 C5 56.45(16) . . . . ?
C2 C3 C4 C8 168.84(13) . . . . ?
C2 C3 C10 C11 51.4(2) . . . . ?
C2 C3 C10 C15 -131.05(16) . . . . ?
C3 C4 C5 N1 -26.53(18) . . . . ?
C3 C4 C5 O3 -147.55(13) . . . . ?
C3 C4 C5 C6 95.96(14) . . . . ?
C3 C4 C8 C7 -98.54(17) . . . . ?
C3 C4 C8 C9 82.06(19) . . . . ?
C3 C10 C11 C12 173.41(16) . . . . ?
C3 C10 C15 C14 -174.07(15) . . . . ?
C4 C3 C10 C11 -71.1(2) . . . . ?
C4 C3 C10 C15 106.38(17) . . . . ?
C4 C5 C6 O4 -161.76(15) . . . . ?
C4 C5 C6 C7 20.24(16) . . . . ?
O2 C4 C5 N1 94.65(16) . . . . ?
O2 C4 C5 O3 -26.36(17) . . . . ?
O2 C4 C5 C6 -142.86(13) . . . . ?
O2 C4 C8 C7 138.58(15) . . . . ?
O2 C4 C8 C9 -40.8(2) . . . . ?
C5 N1 C1 O1 -176.44(15) . . . . ?
C5 N1 C1 C2 2.8(2) . . . . ?
C5 C4 C8 C7 19.06(18) . . . . ?
C5 C4 C8 C9 -160.33(15) . . . . ?
C5 C6 C7 C8 -9.11(19) . . . . ?
O3 C5 C6 O4 82.48(19) . . . . ?
O3 C5 C6 C7 -95.52(15) . . . . ?
C6 C7 C8 C4 -6.6(2) . . . . ?
C6 C7 C8 C9 172.75(16) . . . . ?
O4 C6 C7 C8 173.06(17) . . . . ?
C8 C4 C5 N1 -145.11(14) . . . . ?
C8 C4 C5 O3 93.87(14) . . . . ?
C8 C4 C5 C6 -22.62(15) . . . . ?
C10 C3 C4 O2 59.19(17) . . . . ?
C10 C3 C4 C5 -178.10(13) . . . . ?
C10 C3 C4 C8 -65.71(18) . . . . ?
C10 C11 C12 C13 0.9(3) . . . . ?
C11 C10 C15 C14 3.5(2) . . . . ?
C11 C12 C13 Br1 -175.53(13) . . . . ?
C11 C12 C13 C14 3.1(3) . . . . ?
C12 C13 C14 C15 -3.7(3) . . . . ?
C13 C14 C15 C10 0.3(2) . . . . ?
C15 C10 C11 C12 -4.1(3) . . . . ?
