#------------------------------------------------------------------------------
#$Date: 2024-01-06 11:25:31 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288868 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/96/7159605.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_7159605
loop_
_publ_author_name
'Lee, Stephanie'
'Söhnel, Tilo'
'Sperry, Jonathan'
_publ_section_title
;
 Support studies toward the hicksoane alkaloids reveal cascade reactions
 of a (tryptophanamido)methylglycinate.
;
_journal_issue                   43
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8708
_journal_page_last               8715
_journal_paper_doi               10.1039/d3ob01596c
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H20 N4 O3'
_chemical_formula_sum            'C15 H20 N4 O3'
_chemical_formula_weight         304.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2023-07-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-07-16 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.304(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.2851(13)
_cell_length_b                   5.2346(4)
_cell_length_c                   18.9492(16)
_cell_measurement_reflns_used    1950
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      69.5320
_cell_measurement_theta_min      5.0640
_cell_volume                     1494.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -36.00  14.40   0.80    2.60    --  -46.98  38.00   0.00   63
  2  ω     -8.00  18.40   0.80    2.60    --  -46.98  19.00   0.00   33
  3  ω    -26.00  35.60   0.80    2.60    --  -46.98  19.00  60.00   77
  4  ω    -32.00  29.60   0.80    2.60    --  -46.98  96.00  74.00   77
  5  ω    -45.00 -18.60   0.80   10.60    --  -90.25 111.00   0.00   33
  6  ω    -47.00 -12.60   0.80   10.60    --  -90.25  45.00  30.00   43
  7  ω    -47.00 -11.80   0.80   10.60    --  -90.25  45.00   0.00   44
  8  ω    -50.00 -22.00   0.80   10.60    --  -90.25  45.00 -90.00   35
  9  ω    -49.00 -17.00   0.80   10.60    --  -90.25  45.00-120.00   40
 10  ω    -43.00 -11.80   0.80   10.60    --  -90.25  45.00-150.00   39
 11  ω    -87.00 -24.60   0.80   10.60    --  -90.25  77.00  60.00   78
 12  ω    -79.00 -11.00   0.80   10.60    --  -90.25  96.00  74.00   85
 13  ω     23.00  57.40   0.80    2.60    --   46.98 -96.00 -34.00   43
 14  ω     62.00  86.80   0.80   10.60    --   97.33 -96.00 -34.00   31
 15  ω     61.00  85.80   0.80   10.60    --   97.33 -77.00   0.00   31
 16  ω     40.00  64.80   0.80   10.60    --   97.33 -61.00 -90.00   31
 17  ω     24.00  51.20   0.80   10.60    --   97.33 -77.00   0.00   34
 18  ω     20.00  45.60   0.80   10.60    --   97.33 -45.00 -90.00   32
 19  ω    -29.00  23.00   0.80    2.60    --   46.98 -19.00  30.00   65
 20  ω     26.00  67.60   0.80   10.60    --   97.33 -61.00 120.00   52
 21  ω     32.00  71.20   0.80   10.60    --   97.33 -61.00 150.00   49
 22  ω     20.00  47.20   0.80   10.60    --   97.33 -45.00 120.00   34
 23  ω    140.00 176.00   0.80   10.60    --   97.33 111.00  90.00   45
 24  ω    109.00 143.40   0.80   10.60    --   97.33 178.00 120.00   43
 25  ω     74.00  98.80   0.80   10.60    --   97.33 178.00 120.00   31
 26  ω   -128.00-103.20   0.80   10.60    --  -90.25 -96.00 -34.00   31
 27  ω   -152.00-106.40   0.80   10.60    --  -90.25 -61.00 -30.00   57
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0175935000
_diffrn_orient_matrix_UB_12      0.2575570000
_diffrn_orient_matrix_UB_13      0.0424800000
_diffrn_orient_matrix_UB_21      -0.0922417000
_diffrn_orient_matrix_UB_22      0.0953525000
_diffrn_orient_matrix_UB_23      -0.0532200000
_diffrn_orient_matrix_UB_31      -0.0404494000
_diffrn_orient_matrix_UB_32      -0.1054957000
_diffrn_orient_matrix_UB_33      0.0555774000
_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  0.0507
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4802
_diffrn_reflns_point_group_measured_fraction_full 0.793
_diffrn_reflns_point_group_measured_fraction_max 0.791
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.729
_diffrn_reflns_theta_min         5.874
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.794
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       plank
_exptl_crystal_F_000             648
_exptl_crystal_recrystallization_method MeOH
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 496 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2156
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0514
_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)+(0.0874P)²+0.0661P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1298
_refine_ls_wR_factor_ref         0.1390
_reflns_Friedel_coverage         0.434
_reflns_Friedel_fraction_full    0.544
_reflns_Friedel_fraction_max     0.543
_reflns_number_gt                1870
_reflns_number_total             2156
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01596c2.cif
_cod_data_source_block           syl-06-20_01
_cod_depositor_comments
'Adding full bibliography for 7159603--7159605.cif.'
_cod_database_code               7159605
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C15 H20 N4 O3'
_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.
;
_reflns_odcompleteness_completeness 99.40
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2A = N2-H2B
 0.86 with sigma of 0.02
 H2A-H2B
 1.56 with sigma of 0.02
3.a Riding coordinates:
 N4(H4)
3.b Ternary CH refined with riding coordinates:
 C10(H10)
3.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B), C13(H13A,H13B)
3.d Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C2(H2), C3(H3A), C4(H4A), C5(H5), C8(H8)
3.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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 2.755
_oxdiff_exptl_absorpt_empirical_full_min 0.645
loop_
_space_group_symop_operation_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_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
O1 O 0.20981(18) 1.1033(6) 0.39429(17) 0.0311(7) Uani 1 1 d . . . . .
O2 O 0.2636(2) 0.6030(7) 0.14472(18) 0.0415(8) Uani 1 1 d . . . . .
O3 O 0.1874(2) 0.2381(7) 0.12752(18) 0.0369(8) Uani 1 1 d . . . . .
N1 N -0.1058(2) 0.4782(8) 0.25236(19) 0.0287(8) Uani 1 1 d . . . . .
H1 H -0.141745 0.345770 0.241579 0.034 Uiso 1 1 calc R U . . .
N2 N 0.0945(2) 0.6746(8) 0.4759(2) 0.0297(8) Uani 1 1 d D . . . .
H2A H 0.137(2) 0.657(11) 0.5193(14) 0.036 Uiso 1 1 d D U . . .
H2B H 0.076(3) 0.602(10) 0.4339(16) 0.036 Uiso 1 1 d D U . . .
N3 N 0.2056(2) 0.6731(7) 0.39398(19) 0.0245(8) Uani 1 1 d . . . . .
H3 H 0.180470 0.533599 0.402224 0.029 Uiso 1 1 calc R U . . .
N4 N 0.2530(2) 0.6810(7) 0.28505(19) 0.0276(8) Uani 1 1 d . . . . .
H4 H 0.224846 0.821241 0.268152 0.033 Uiso 1 1 d R U . . .
C1 C -0.0648(2) 0.5737(9) 0.2067(2) 0.0275(10) Uani 1 1 d . . . . .
C2 C -0.0698(3) 0.4961(11) 0.1355(2) 0.0345(11) Uani 1 1 d . . . . .
H2 H -0.104032 0.351756 0.110924 0.041 Uiso 1 1 calc R U . . .
C3 C -0.0231(3) 0.6362(12) 0.1016(3) 0.0418(12) Uani 1 1 d . . . . .
H3A H -0.024442 0.585649 0.052996 0.050 Uiso 1 1 calc R U . . .
C4 C 0.0264(3) 0.8514(11) 0.1373(3) 0.0418(13) Uani 1 1 d . . . . .
H4A H 0.055786 0.948645 0.111581 0.050 Uiso 1 1 calc R U . . .
C5 C 0.0330(3) 0.9238(10) 0.2089(3) 0.0349(11) Uani 1 1 d . . . . .
H5 H 0.068628 1.066065 0.233408 0.042 Uiso 1 1 calc R U . . .
C6 C -0.0134(3) 0.7863(9) 0.2457(2) 0.0261(9) Uani 1 1 d . . . . .
C7 C -0.0245(2) 0.8121(8) 0.3165(2) 0.0239(9) Uani 1 1 d . . . . .
C8 C -0.0819(2) 0.6207(10) 0.3168(2) 0.0282(10) Uani 1 1 d . . . . .
H8 H -0.102225 0.591805 0.356945 0.034 Uiso 1 1 calc R U . . .
C9 C 0.0181(3) 1.0018(9) 0.3787(2) 0.0272(9) Uani 1 1 d . . . . .
H9A H -0.024030 1.042654 0.403386 0.033 Uiso 1 1 calc R U . . .
H9B H 0.029148 1.161215 0.355572 0.033 Uiso 1 1 calc R U . . .
C10 C 0.1062(3) 0.9126(9) 0.4405(2) 0.0264(9) Uani 1 1 d . . . . .
H10 H 0.124529 1.046256 0.481220 0.032 Uiso 1 1 calc R U . . .
C11 C 0.1785(2) 0.9008(9) 0.4073(2) 0.0244(9) Uani 1 1 d . . . . .
C12 C 0.2775(2) 0.6540(9) 0.3656(2) 0.0255(9) Uani 1 1 d . . . . .
H12A H 0.322172 0.786630 0.391286 0.031 Uiso 1 1 calc R U . . .
H12B H 0.306572 0.485847 0.380985 0.031 Uiso 1 1 calc R U . . .
C13 C 0.2077(3) 0.4622(9) 0.2393(2) 0.0291(10) Uani 1 1 d . . . . .
H13A H 0.143164 0.476092 0.227278 0.035 Uiso 1 1 calc R U . . .
H13B H 0.229279 0.303373 0.268901 0.035 Uiso 1 1 calc R U . . .
C14 C 0.2237(3) 0.4484(9) 0.1665(2) 0.0285(9) Uani 1 1 d . . . . .
C15 C 0.1975(3) 0.1981(11) 0.0569(3) 0.0427(13) Uani 1 1 d . . . . .
H15A H 0.165697 0.331905 0.020654 0.064 Uiso 1 1 calc R U . . .
H15B H 0.173207 0.030653 0.036200 0.064 Uiso 1 1 calc R U . . .
H15C H 0.260674 0.204095 0.065158 0.064 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'
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
C14 O3 C15 117.2(4) . . ?
C1 N1 H1 125.5 . . ?
C8 N1 H1 125.5 . . ?
C8 N1 C1 109.0(4) . . ?
H2A N2 H2B 138(4) . . ?
C10 N2 H2A 110(4) . . ?
C10 N2 H2B 91(4) . . ?
C11 N3 H3 120.0 . . ?
C11 N3 C12 120.1(3) . . ?
C12 N3 H3 120.0 . . ?
C12 N4 H4 112.0 . . ?
C12 N4 C13 115.5(3) . . ?
C13 N4 H4 111.8 . . ?
N1 C1 C2 130.3(4) . . ?
N1 C1 C6 106.8(4) . . ?
C2 C1 C6 122.9(4) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 C1 117.5(5) . . ?
C3 C2 H2 121.3 . . ?
C2 C3 H3A 119.3 . . ?
C2 C3 C4 121.3(4) . . ?
C4 C3 H3A 119.3 . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 C3 120.9(4) . . ?
C5 C4 H4A 119.5 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.6(5) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C7 107.7(4) . . ?
C5 C6 C1 117.7(4) . . ?
C5 C6 C7 134.6(4) . . ?
C6 C7 C9 128.2(4) . . ?
C8 C7 C6 105.4(4) . . ?
C8 C7 C9 126.5(4) . . ?
N1 C8 C7 111.1(3) . . ?
N1 C8 H8 124.4 . . ?
C7 C8 H8 124.4 . . ?
C7 C9 H9A 108.6 . . ?
C7 C9 H9B 108.6 . . ?
C7 C9 C10 114.7(4) . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
N2 C10 C9 111.2(3) . . ?
N2 C10 H10 107.1 . . ?
N2 C10 C11 114.1(4) . . ?
C9 C10 H10 107.1 . . ?
C11 C10 C9 109.9(3) . . ?
C11 C10 H10 107.1 . . ?
O1 C11 N3 122.4(3) . . ?
O1 C11 C10 119.0(4) . . ?
N3 C11 C10 118.6(4) . . ?
N3 C12 H12A 108.2 . . ?
N3 C12 H12B 108.2 . . ?
N4 C12 N3 116.6(3) . . ?
N4 C12 H12A 108.2 . . ?
N4 C12 H12B 108.2 . . ?
H12A C12 H12B 107.3 . . ?
N4 C13 H13A 109.4 . . ?
N4 C13 H13B 109.4 . . ?
N4 C13 C14 111.1(4) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
O2 C14 O3 123.2(4) . . ?
O2 C14 C13 126.0(4) . . ?
O3 C14 C13 110.8(4) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
O1 C11 1.242(5) . ?
O2 C14 1.205(5) . ?
O3 C14 1.333(6) . ?
O3 C15 1.426(5) . ?
N1 H1 0.8800 . ?
N1 C1 1.372(5) . ?
N1 C8 1.356(6) . ?
N2 H2A 0.85(2) . ?
N2 H2B 0.83(2) . ?
N2 C10 1.462(6) . ?
N3 H3 0.8800 . ?
N3 C11 1.328(6) . ?
N3 C12 1.465(4) . ?
N4 H4 0.8600 . ?
N4 C12 1.430(5) . ?
N4 C13 1.457(6) . ?
C1 C2 1.381(6) . ?
C1 C6 1.420(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.379(7) . ?
C3 H3A 0.9500 . ?
C3 C4 1.400(8) . ?
C4 H4A 0.9500 . ?
C4 C5 1.374(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.405(6) . ?
C6 C7 1.425(6) . ?
C7 C8 1.372(6) . ?
C7 C9 1.496(6) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.540(5) . ?
C10 H10 1.0000 . ?
C10 C11 1.531(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.499(6) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
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
N1 C1 C2 C3 177.6(5) . . . . ?
N1 C1 C6 C5 -177.8(4) . . . . ?
N1 C1 C6 C7 0.6(5) . . . . ?
N2 C10 C11 O1 -161.4(4) . . . . ?
N2 C10 C11 N3 18.3(5) . . . . ?
N4 C13 C14 O2 -4.4(7) . . . . ?
N4 C13 C14 O3 175.6(3) . . . . ?
C1 N1 C8 C7 -0.5(5) . . . . ?
C1 C2 C3 C4 -1.0(7) . . . . ?
C1 C6 C7 C8 -0.8(5) . . . . ?
C1 C6 C7 C9 177.9(4) . . . . ?
C2 C1 C6 C5 1.0(6) . . . . ?
C2 C1 C6 C7 179.4(4) . . . . ?
C2 C3 C4 C5 2.8(8) . . . . ?
C3 C4 C5 C6 -2.6(8) . . . . ?
C4 C5 C6 C1 0.7(7) . . . . ?
C4 C5 C6 C7 -177.1(5) . . . . ?
C5 C6 C7 C8 177.2(5) . . . . ?
C5 C6 C7 C9 -4.1(8) . . . . ?
C6 C1 C2 C3 -0.9(7) . . . . ?
C6 C7 C8 N1 0.8(5) . . . . ?
C6 C7 C9 C10 -91.2(5) . . . . ?
C7 C9 C10 N2 -57.3(4) . . . . ?
C7 C9 C10 C11 69.9(5) . . . . ?
C8 N1 C1 C2 -178.8(5) . . . . ?
C8 N1 C1 C6 -0.1(5) . . . . ?
C8 C7 C9 C10 87.4(5) . . . . ?
C9 C7 C8 N1 -178.0(4) . . . . ?
C9 C10 C11 O1 73.0(5) . . . . ?
C9 C10 C11 N3 -107.3(4) . . . . ?
C11 N3 C12 N4 -83.5(5) . . . . ?
C12 N3 C11 O1 2.4(6) . . . . ?
C12 N3 C11 C10 -177.3(3) . . . . ?
C12 N4 C13 C14 -152.4(3) . . . . ?
C13 N4 C12 N3 -74.6(5) . . . . ?
C15 O3 C14 O2 0.3(7) . . . . ?
C15 O3 C14 C13 -179.7(4) . . . . ?
