# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
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#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_I
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        bicyclo[3.3.1]nonane-2,6-dione
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C50 H43 N8 O4'
_chemical_formula_weight         819.9
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration ?

#=======================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P 41'
_symmetry_space_group_name_Hall  'P 41'
_symmetry_Int_Tables_number      76

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,z+1/2
3 -y,x,z+1/4
4 y,-x,z+3/4

_cell_length_a                   13.4574(5)
_cell_length_b                   13.4574(5)
_cell_length_c                   23.307(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4220.9(4)

loop_
_jana_cell_twin_matrix_id
_jana_cell_twin_volume_fraction
_jana_cell_twin_matrix_1_1
_jana_cell_twin_matrix_1_2
_jana_cell_twin_matrix_1_3
_jana_cell_twin_matrix_2_1
_jana_cell_twin_matrix_2_2
_jana_cell_twin_matrix_2_3
_jana_cell_twin_matrix_3_1
_jana_cell_twin_matrix_3_2
_jana_cell_twin_matrix_3_3
1 0.5 1 0 0 0 1 0 0 0 1
2 0.5 1 0 0 0 -1 0 0 0 -1
_cell_formula_units_Z            4

_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?
_cell_measurement_temperature    293
_cell_special_details            
; ?
;

_exptl_crystal_density_diffrn    1.2899
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1724

_exptl_absorpt_coefficient_mu    0.084
_exptl_crystal_description       Platelet
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            Transparent
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,z+1/2
3 -y,x,z+1/4
4 y,-x,z+3/4

#=======================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      293
_diffrn_source                   ?
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device       ?
_diffrn_measurement_device_type  ?
_diffrn_detector                 ?
_diffrn_detector_area_resol_mean ?
_diffrn_measurement_method       ?
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            9473
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         28.86
_diffrn_reflns_theta_full        27.77
_diffrn_measured_fraction_theta_max 0.91
_diffrn_measured_fraction_theta_full 0.98
_diffrn_reflns_av_r_equivalents  0
_diffrn_reflns_av_uneti/neti     0.2833
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_reduction_process ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          X-ray

#=======================================================================

# 8. REFINEMENT DATA

_refine_special_details          Twin

_reflns_number_total             9473
_reflns_number_gt                1792
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0834
_refine_ls_wR_factor_gt          0.1437
_refine_ls_R_factor_all          0.3349
_refine_ls_wR_factor_ref         0.2336
_refine_ls_goodness_of_fit_ref   1.16
_refine_ls_goodness_of_fit_gt    1.71
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         9473
_refine_ls_number_parameters     249
_refine_ls_number_restraints     68
_refine_ls_number_constraints    173
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(I)+0.0004I²)
_refine_ls_hydrogen_treatment    constr
_refine_ls_shift/su_max          0.0475
_refine_ls_shift/su_mean         0.0066
_refine_diff_density_max         1.54
_refine_diff_density_min         -0.61
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;  4315 of Friedel pairs used in the refinement
;
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
C 0.0033 0.0016 'International Tables Vol C tables 4.2.6.8 and 6.1.1.4' 2.31
20.843901 1.02 10.2075 1.5886 0.5687 0.865 51.651199 0.2156
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.4'
0.493002 10.5109 0.322912 26.1257 0.140191 3.14236 0.04081 57.799702 0.003038
N 0.0061 0.0033 'International Tables Vol C tables 4.2.6.8 and 6.1.1.4' 12.2126
0.0057 3.1322 9.8933 2.0125 28.997499 1.1663 0.5826 -11.529
O 0.0106 0.0060 'International Tables Vol C tables 4.2.6.8 and 6.1.1.4' 3.0485
13.2771 2.2868 5.7011 1.5463 0.3239 0.867 32.908901 0.2508

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  ?
_computing_molecular_graphics    ?
_computing_publication_material  ?

#=======================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1_1 N 0.4379(9) 0.2277(7) -0.0170(4) Uiso 0.059(4) 4 1 d . . .
N1_2 N 0.7253(8) -0.0612(9) 0.0101(5) Uiso 0.070(4) 4 1 d . . .
C1_1 C 0.4673(9) 0.3080(7) 0.0150(4) Uiso 0.050(4) 4 1 d . . .
C1_2 C 0.8089(8) -0.0426(10) -0.0217(5) Uiso 0.068(5) 4 1 d . . .
N2_1 N 0.5492(8) 0.3855(7) 0.0976(4) Uiso 0.056(3) 4 1 d . . .
N2_2 N 0.8862(7) 0.0452(8) -0.0999(5) Uiso 0.057(3) 4 1 d . . .
C2_1 C 0.4323(9) 0.3982(6) -0.0059(4) Uiso 0.042(4) 4 1 d . . .
C2_2 C 0.9025(7) -0.0693(9) -0.0017(5) Uiso 0.044(4) 4 1 d . . .
C3_1 C 0.4572(9) 0.4826(7) 0.0253(4) Uiso 0.053(4) 4 1 d . . .
C3_2 C 0.9853(7) -0.0389(9) -0.0326(4) Uiso 0.043(4) 4 1 d . . .
N3_1 N 0.5981(7) 0.7193(9) -0.0452(4) Uiso 0.075(4) 4 1 d . . .
N3_2 N 1.2255(9) 0.0915(8) 0.0425(4) Uiso 0.063(4) 4 1 d . . .
C4_1 C 0.5214(9) 0.3045(7) 0.0658(4) Uiso 0.046(4) 4 1 d . . .
C4_2 C 0.8027(8) 0.0117(10) -0.0723(5) Uiso 0.062(4) 4 1 d . . .
C5_1 C 0.4232(9) 0.5888(6) 0.0106(5) Uiso 0.066(4) 4 1 d . . .
C5_2 C 1.0837(6) -0.0696(8) -0.0041(5) Uiso 0.051(4) 4 1 d . . .
C6_1 C 0.4658(9) 0.1389(7) 0.0068(4) Uiso 0.057(4) 4 1 d . . .
C6_2 C 0.6357(8) -0.0276(10) -0.0098(5) Uiso 0.055(4) 4 1 d . . .
C7_1 C 0.5245(7) 0.1282(6) 0.0554(4) Uiso 0.027(3) 4 1 d . . .
C7_2 C 0.6255(9) 0.0155(11) -0.0636(5) Uiso 0.093(6) 4 1 d . . .
C8_1 C 0.5483(9) 0.2120(6) 0.0874(5) Uiso 0.054(4) 4 1 d . . .
C8_2 C 0.7113(8) 0.0459(10) -0.0918(6) Uiso 0.073(5) 4 1 d . . .
C9_1 C 0.5161(10) 0.4727(7) 0.0740(5) Uiso 0.058(4) 4 1 d . . .
C9_2 C 0.9794(8) 0.0178(10) -0.0824(5) Uiso 0.060(4) 4 1 d . . .
C10_1 C 0.6940(7) 0.7221(8) -0.0649(4) Uiso 0.041(3) 4 1 d . . .
C10_2 C 1.2365(11) 0.1783(8) 0.0726(5) Uiso 0.090(5) 4 1 d . . .
C11_1 C 0.6721(8) 0.6317(10) 0.0403(5) Uiso 0.073(5) 4 1 d . . .
C11_2 C 1.1402(10) 0.1751(8) -0.0313(5) Uiso 0.064(4) 4 1 d . . .
C12_1 C 0.5494(9) 0.0223(6) 0.0759(5) Uiso 0.053(4) 4 1 d . . .
C12_2 C 0.5232(8) 0.0478(12) -0.0867(5) Uiso 0.085(5) 4 1 d . . .
C13_1 C 0.5530(7) 0.5637(7) 0.1078(5) Uiso 0.048(3) 4 1 d . . .
C13_2 C 1.0676(8) 0.0616(7) -0.1160(6) Uiso 0.087(5) 4 1 d . . .
C14_1 C 0.5505(8) -0.0601(8) 0.0301(4) Uiso 0.051(4) 4 1 d . . .
C14_2 C 0.4520(10) 0.0514(7) -0.0351(4) Uiso 0.063(5) 4 1 d . . .
C15 C 0.4528(8) -0.0492(9) -0.0036(6) Uiso 0.055(3) 4 1 d . . .
C16_1 C 0.4927(8) 0.6700(9) 0.0343(5) Uiso 0.063(5) 4 1 d . . .
C16_2 C 1.1720(9) -0.0190(8) -0.0343(5) Uiso 0.074(5) 4 1 d . . .
C17_1 C 0.5973(7) 0.6753(10) 0.0078(4) Uiso 0.056(4) 4 1 d . . .
C17_2 C 1.1770(10) 0.0866(8) -0.0091(5) Uiso 0.060(4) 4 1 d . . .
C18_1 C 0.7625(8) 0.6340(10) 0.0115(5) Uiso 0.067(4) 4 1 d . . .
C18_2 C 1.1467(11) 0.2662(9) -0.0035(5) Uiso 0.102(6) 4 1 d . . .
C19_1 C 0.7789(8) 0.6804(11) -0.0410(5) Uiso 0.087(5) 4 1 d . . .
C19_2 C 1.1983(10) 0.2644(8) 0.0482(5) Uiso 0.064(4) 4 1 d . . .
C20_1 C 0.8718(9) 0.6894(11) -0.0666(6) Uiso 0.100(6) 4 1 d . . .
N20_2 N 1.1965(12) 0.3545(9) 0.0757(6) Uiso 0.135(6) 4 1 d . . .
C21_1 C 0.4948(12) 0.6613(9) 0.1001(5) Uiso 0.116(7) 4 1 d . . .
C21_2 C 1.1535(9) -0.0082(9) -0.0992(5) Uiso 0.062(5) 4 1 d . . .
C22_1 C 0.6646(8) 0.5857(10) 0.1006(5) Uiso 0.084(5) 4 1 d . . .
C22_2 C 1.0910(9) 0.1646(9) -0.0906(4) Uiso 0.063(4) 4 1 d . . .
C23_1 C 0.7030(10) 0.7684(10) -0.1180(5) Uiso 0.082(4) 4 1 d . . .
C23_2 C 1.2889(9) 0.1743(9) 0.1240(5) Uiso 0.064(4) 4 1 d . . .
C24_1 C 0.7919(9) 0.7737(12) -0.1482(7) Uiso 0.113(6) 4 1 d . . .
N24_2 N 1.2914(10) 0.2674(9) 0.1478(6) Uiso 0.115(5) 4 1 d . . .
C25_1 C 0.8745(12) 0.7361(11) -0.1197(6) Uiso 0.108(6) 4 1 d . . .
C25_2 C 1.2524(10) 0.3525(11) 0.1248(6) Uiso 0.100(6) 4 1 d . . .
O1_1 O 0.6174(10) 0.8134(10) -0.1446(6) Uiso 0.172(5) 4 1 d . . .
C26_1 C 0.6035(16) 0.8789(17) -0.1968(10) Uiso 0.256(10) 4 1 d . . .
H1c2_1 H 0.392889 0.401983 -0.040122 Uiso 0.05 4 1 d . . .
H1c2_2 H 0.909684 -0.107897 0.032714 Uiso 0.053 4 1 d . . .
H1c5_1 H 0.357191 0.599251 0.024934 Uiso 0.0792 4 1 d . . .
H2c5_1 H 0.417829 0.5957 -0.030281 Uiso 0.0792 4 1 d . . .
H1c5_2 H 1.082792 -0.050653 0.035606 Uiso 0.0613 4 1 d . . .
H2c5_2 H 1.091243 -0.140476 -0.006384 Uiso 0.0613 4 1 d . . .
H1c8_1 H 0.582344 0.206222 0.123409 Uiso 0.0653 4 1 d . . .
H1c8_2 H 0.707462 0.08974 -0.124255 Uiso 0.088 4 1 d . . .
H1c12_1 H 0.505032 0.003924 0.106383 Uiso 0.0632 4 1 d . . .
H2c12_1 H 0.61173 0.022877 0.095907 Uiso 0.0632 4 1 d . . .
H1c12_2 H 0.528421 0.112797 -0.103368 Uiso 0.1024 4 1 d . . .
H2c12_2 H 0.49982 -0.000353 -0.113897 Uiso 0.1024 4 1 d . . .
H1c13_1 H 0.540004 0.541233 0.146188 Uiso 0.0572 4 1 d . . .
H1c13_2 H 1.056298 0.067213 -0.156538 Uiso 0.1049 4 1 d . . .
H1c14_1 H 0.557768 -0.126393 0.044787 Uiso 0.0613 4 1 d . . .
H1c14_2 H 0.387596 0.063924 -0.051276 Uiso 0.0759 4 1 d . . .
H1c15 H 0.447463 -0.102049 -0.031076 Uiso 0.0655 4 1 d . . .
H2c15 H 0.397629 -0.052207 0.022476 Uiso 0.0655 4 1 d . . .
H1c16_1 H 0.465045 0.732606 0.022689 Uiso 0.0754 4 1 d . . .
H1c16_2 H 1.231333 -0.057357 -0.028819 Uiso 0.0884 4 1 d . . .
H1c18_1 H 0.81789 0.600978 0.029137 Uiso 0.0803 4 1 d . . .
H1c18_2 H 1.117741 0.325821 -0.018726 Uiso 0.1223 4 1 d . . .
H1c20_1 H 0.930951 0.664717 -0.048475 Uiso 0.1205 4 1 d . . .
H1c21_1 H 0.428305 0.652859 0.114249 Uiso 0.1388 4 1 d . . .
H2c21_1 H 0.53249 0.715375 0.115886 Uiso 0.1388 4 1 d . . .
H1c21_2 H 1.142559 -0.072582 -0.115735 Uiso 0.0742 4 1 d . . .
H2c21_2 H 1.213513 0.013432 -0.117684 Uiso 0.0742 4 1 d . . .
H1c22_1 H 0.68491 0.633752 0.128715 Uiso 0.1013 4 1 d . . .
H2c22_1 H 0.701211 0.524535 0.101646 Uiso 0.1013 4 1 d . . .
H1c22_2 H 1.127212 0.203178 -0.118193 Uiso 0.0751 4 1 d . . .
H2c22_2 H 1.032559 0.205402 -0.092142 Uiso 0.0751 4 1 d . . .
H1c23_2 H 1.318641 0.115814 0.140151 Uiso 0.0771 4 1 d . . .
H1c24_1 H 0.795999 0.801441 -0.186052 Uiso 0.1357 4 1 d . . .
H1c25_1 H 0.93799 0.742771 -0.138132 Uiso 0.1291 4 1 d . . .
H1c25_2 H 1.264796 0.414231 0.144205 Uiso 0.1203 4 1 d . . .
H1c26_1 H 0.535499 0.900255 -0.198856 Uiso 0.3066 4 1 d . . .
H2c26_1 H 0.646075 0.935841 -0.19379 Uiso 0.3066 4 1 d . . .
H3c26_1 H 0.619976 0.842034 -0.230714 Uiso 0.3066 4 1 d . . .
O2 O 0.6226(15) -0.1230(16) 0.2952(11) Uiso 0.291(10) 4 1 d . . .
O3 O 0.3374(10) 0.2425(10) -0.1204(6) Uiso 0.138(5) 4 1 d . . .
O4 O 0.7538(17) -0.1634(16) 0.1080(9) Uiso 0.272(10) 4 1 d . . .
C96 C 0.634(3) -0.177(3) 0.240(2) Uiso 0.51(3) 4 1 d . . .
C97 C 0.7370(17) -0.1804(15) 0.2538(13) Uiso 0.256(14) 4 1 d . . .
H1c96 H 0.605521 -0.24192 0.243997 Uiso 0.6074 4 1 d . . .
H2c96 H 0.623029 -0.131537 0.209131 Uiso 0.6074 4 1 d . . .
H1c97 H 0.750451 -0.238252 0.276599 Uiso 0.307 4 1 d . . .
H2c97 H 0.774765 -0.183668 0.218861 Uiso 0.307 4 1 d . . .
H3c97 H 0.755399 -0.121908 0.274785 Uiso 0.307 4 1 d . . .


loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1_1 C1_1 . . 1.371(14) ?
N1_1 C6_1 . . 1.370(14) ?
N1_2 C1_2 . . 1.370(16) ?
N1_2 C6_2 . . 1.369(16) ?
C1_1 C2_1 . . 1.390(13) ?
C1_1 C4_1 . . 1.391(14) ?
C1_2 C2_2 . . 1.390(15) ?
C1_2 C4_2 . . 1.390(17) ?
N2_1 C4_1 . . 1.370(14) ?
N2_1 C9_1 . . 1.370(14) ?
N2_2 C4_2 . . 1.371(15) ?
N2_2 C9_2 . . 1.369(15) ?
C2_1 C3_1 . . 1.390(13) ?
C2_1 H1c2_1 . . 0.959(10) ?
C2_2 C3_2 . . 1.388(14) ?
C2_2 H1c2_2 . . 0.960(12) ?
C3_1 C5_1 . . 1.539(13) ?
C3_1 C9_1 . . 1.391(16) ?
C3_2 C5_2 . . 1.538(13) ?
C3_2 C9_2 . . 1.391(16) ?
N3_1 C10_1 . . 1.370(13) ?
N3_1 C17_1 . . 1.370(14) ?
N3_2 C10_2 . . 1.371(15) ?
N3_2 C17_2 . . 1.370(16) ?
C4_1 C8_1 . . 1.391(13) ?
C4_2 C8_2 . . 1.390(16) ?
C5_1 C16_1 . . 1.541(15) ?
C5_1 H1c5_1 . . 0.959(12) ?
C5_1 H2c5_1 . . 0.960(12) ?
C5_2 C16_2 . . 1.540(15) ?
C5_2 H1c5_2 . . 0.960(12) ?
C5_2 H2c5_2 . . 0.961(11) ?
C6_1 C7_1 . . 1.388(14) ?
C6_1 C14_2 . . 1.541(13) ?
C6_2 C7_2 . . 1.388(17) ?
C6_2 C14_1 . . 1.540(15) ?
C7_1 C8_1 . . 1.389(13) ?
C7_1 C12_1 . . 1.540(12) ?
C7_2 C8_2 . . 1.390(17) ?
C7_2 C12_2 . . 1.541(17) ?
C8_1 H1c8_1 . . 0.959(12) ?
C8_2 H1c8_2 . . 0.961(14) ?
C9_1 C13_1 . . 1.538(15) ?
C9_2 C13_2 . . 1.539(16) ?
C10_1 C19_1 . . 1.389(15) ?
C10_1 C23_1 . . 1.391(15) ?
C10_2 C19_2 . . 1.389(16) ?
C10_2 C23_2 . . 1.391(17) ?
C11_1 C17_1 . . 1.390(15) ?
C11_1 C18_1 . . 1.390(16) ?
C11_1 C22_1 . . 1.539(17) ?
C11_2 C17_2 . . 1.390(16) ?
C11_2 C18_2 . . 1.389(16) ?
C11_2 C22_2 . . 1.539(16) ?
C12_1 C14_1 . . 1.539(14) ?
C12_1 H1c12_1 . . 0.960(12) ?
C12_1 H2c12_1 . . 0.960(12) ?
C12_2 C14_2 . . 1.538(16) ?
C12_2 H1c12_2 . . 0.960(15) ?
C12_2 H2c12_2 . . 0.960(14) ?
C13_1 C21_1 . . 1.540(16) ?
C13_1 C22_1 . . 1.540(14) ?
C13_1 H1c13_1 . . 0.960(11) ?
C13_2 C21_2 . . 1.540(16) ?
C13_2 C22_2 . . 1.540(16) ?
C13_2 H1c13_2 . . 0.960(14) ?
C14_1 C15 . . 1.539(16) ?
C14_1 H1c14_1 . . 0.961(11) ?
C14_2 C15 . . 1.540(16) ?
C14_2 H1c14_2 . . 0.960(13) ?
C15 H1c15 . . 0.960(13) ?
C15 H2c15 . . 0.960(12) ?
C16_1 C17_1 . . 1.539(14) ?
C16_1 C21_1 . . 1.538(16) ?
C16_1 H1c16_1 . . 0.960(12) ?
C16_2 C17_2 . . 1.539(15) ?
C16_2 C21_2 . . 1.540(16) ?
C16_2 H1c16_2 . . 0.959(12) ?
C18_1 C19_1 . . 1.391(17) ?
C18_1 H1c18_1 . . 0.960(12) ?
C18_2 C19_2 . . 1.391(17) ?
C18_2 H1c18_2 . . 0.960(13) ?
C19_1 C20_1 . . 1.391(17) ?
C19_2 N20_2 . . 1.372(17) ?
C20_1 C25_1 . . 1.39(2) ?
C20_1 H1c20_1 . . 0.960(13) ?
N20_2 C25_2 . . 1.37(2) ?
C21_1 H1c21_1 . . 0.960(16) ?
C21_1 H2c21_1 . . 0.960(13) ?
C21_2 H1c21_2 . . 0.960(12) ?
C21_2 H2c21_2 . . 0.961(12) ?
C22_1 H1c22_1 . . 0.960(12) ?
C22_1 H2c22_1 . . 0.960(13) ?
C22_2 H1c22_2 . . 0.959(11) ?
C22_2 H2c22_2 . . 0.960(12) ?
C23_1 C24_1 . . 1.390(19) ?
C23_1 O1_1 . . 1.442(19) ?
C23_2 N24_2 . . 1.371(17) ?
C23_2 H1c23_2 . . 0.960(12) ?
C24_1 C25_1 . . 1.39(2) ?
C24_1 H1c24_1 . . 0.960(16) ?
N24_2 C25_2 . . 1.369(19) ?
C25_1 H1c25_1 . . 0.961(16) ?
C25_2 H1c25_2 . . 0.960(15) ?
O1_1 C26_1 . . 1.51(3) ?
C26_1 H1c26_1 . . 0.96(2) ?
C26_1 H2c26_1 . . 0.96(2) ?
C26_1 H3c26_1 . . 0.96(2) ?
O2 C96 . . 1.49(5) ?
C96 C97 . . 1.42(5) ?
C96 H1c96 . . 0.96(4) ?
C96 H2c96 . . 0.96(4) ?
C97 H1c97 . . 0.96(2) ?
C97 H2c97 . . 0.96(3) ?
C97 H3c97 . . 0.96(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1_1 N1_1 C6_1 . . . 112.8(9) ?
C1_2 N1_2 C6_2 . . . 118.7(11) ?
N1_1 C1_1 C2_1 . . . 113.6(9) ?
N1_1 C1_1 C4_1 . . . 126.0(9) ?
C2_1 C1_1 C4_1 . . . 120.3(9) ?
N1_2 C1_2 C2_2 . . . 121.0(11) ?
N1_2 C1_2 C4_2 . . . 120.4(10) ?
C2_2 C1_2 C4_2 . . . 118.3(10) ?
C4_1 N2_1 C9_1 . . . 112.0(9) ?
C4_2 N2_2 C9_2 . . . 121.5(11) ?
C1_1 C2_1 C3_1 . . . 116.7(9) ?
C1_1 C2_1 H1c2_1 . . . 121.7(9) ?
C3_1 C2_1 H1c2_1 . . . 121.7(9) ?
C1_2 C2_2 C3_2 . . . 118.5(11) ?
C1_2 C2_2 H1c2_2 . . . 120.7(10) ?
C3_2 C2_2 H1c2_2 . . . 120.8(9) ?
C2_1 C3_1 C5_1 . . . 124.8(9) ?
C2_1 C3_1 C9_1 . . . 119.1(9) ?
C5_1 C3_1 C9_1 . . . 116.1(9) ?
C2_2 C3_2 C5_2 . . . 112.8(9) ?
C2_2 C3_2 C9_2 . . . 123.3(9) ?
C5_2 C3_2 C9_2 . . . 123.8(9) ?
C10_1 N3_1 C17_1 . . . 108.7(9) ?
C10_2 N3_2 C17_2 . . . 122.8(10) ?
C1_1 C4_1 N2_1 . . . 125.2(9) ?
C1_1 C4_1 C8_1 . . . 118.3(9) ?
N2_1 C4_1 C8_1 . . . 116.4(9) ?
C1_2 C4_2 N2_2 . . . 121.5(10) ?
C1_2 C4_2 C8_2 . . . 120.3(11) ?
N2_2 C4_2 C8_2 . . . 117.6(11) ?
C3_1 C5_1 C16_1 . . . 113.5(9) ?
C3_1 C5_1 H1c5_1 . . . 109.5(9) ?
C3_1 C5_1 H2c5_1 . . . 109.5(8) ?
C16_1 C5_1 H1c5_1 . . . 109.5(9) ?
C16_1 C5_1 H2c5_1 . . . 109.4(9) ?
H1c5_1 C5_1 H2c5_1 . . . 105.2(11) ?
C3_2 C5_2 C16_2 . . . 110.4(9) ?
C3_2 C5_2 H1c5_2 . . . 109.5(8) ?
C3_2 C5_2 H2c5_2 . . . 109.5(9) ?
C16_2 C5_2 H1c5_2 . . . 109.5(9) ?
C16_2 C5_2 H2c5_2 . . . 109.4(9) ?
H1c5_2 C5_2 H2c5_2 . . . 108.6(11) ?
N1_1 C6_1 C7_1 . . . 125.2(9) ?
N1_1 C6_1 C14_2 . . . 112.1(8) ?
C7_1 C6_1 C14_2 . . . 120.4(9) ?
N1_2 C6_2 C7_2 . . . 122.1(11) ?
N1_2 C6_2 C14_1 . . . 110.9(10) ?
C7_2 C6_2 C14_1 . . . 126.2(10) ?
C6_1 C7_1 C8_1 . . . 119.0(8) ?
C6_1 C7_1 C12_1 . . . 118.2(8) ?
C8_1 C7_1 C12_1 . . . 122.3(9) ?
C6_2 C7_2 C8_2 . . . 117.9(11) ?
C6_2 C7_2 C12_2 . . . 121.5(10) ?
C8_2 C7_2 C12_2 . . . 119.6(11) ?
C4_1 C8_1 C7_1 . . . 118.2(10) ?
C4_1 C8_1 H1c8_1 . . . 120.9(9) ?
C7_1 C8_1 H1c8_1 . . . 120.9(8) ?
C4_2 C8_2 C7_2 . . . 118.9(12) ?
C4_2 C8_2 H1c8_2 . . . 120.6(11) ?
C7_2 C8_2 H1c8_2 . . . 120.6(11) ?
N2_1 C9_1 C3_1 . . . 126.5(9) ?
N2_1 C9_1 C13_1 . . . 111.8(10) ?
C3_1 C9_1 C13_1 . . . 121.7(9) ?
N2_2 C9_2 C3_2 . . . 116.6(10) ?
N2_2 C9_2 C13_2 . . . 116.8(10) ?
C3_2 C9_2 C13_2 . . . 126.2(10) ?
N3_1 C10_1 C19_1 . . . 129.0(10) ?
N3_1 C10_1 C23_1 . . . 113.1(10) ?
C19_1 C10_1 C23_1 . . . 117.8(10) ?
N3_2 C10_2 C19_2 . . . 117.5(11) ?
N3_2 C10_2 C23_2 . . . 117.6(11) ?
C19_2 C10_2 C23_2 . . . 124.9(11) ?
C17_1 C11_1 C18_1 . . . 111.2(10) ?
C17_1 C11_1 C22_1 . . . 128.3(10) ?
C18_1 C11_1 C22_1 . . . 120.5(10) ?
C17_2 C11_2 C18_2 . . . 124.1(11) ?
C17_2 C11_2 C22_2 . . . 114.1(10) ?
C18_2 C11_2 C22_2 . . . 121.8(10) ?
C7_1 C12_1 C14_1 . . . 117.0(9) ?
C7_1 C12_1 H1c12_1 . . . 109.4(9) ?
C7_1 C12_1 H2c12_1 . . . 109.5(8) ?
C14_1 C12_1 H1c12_1 . . . 109.5(8) ?
C14_1 C12_1 H2c12_1 . . . 109.5(9) ?
H1c12_1 C12_1 H2c12_1 . . . 100.7(11) ?
C7_2 C12_2 C14_2 . . . 107.0(9) ?
C7_2 C12_2 H1c12_2 . . . 109.5(11) ?
C7_2 C12_2 H2c12_2 . . . 109.5(13) ?
C14_2 C12_2 H1c12_2 . . . 109.5(12) ?
C14_2 C12_2 H2c12_2 . . . 109.5(11) ?
H1c12_2 C12_2 H2c12_2 . . . 111.8(12) ?
C9_1 C13_1 C21_1 . . . 117.1(9) ?
C9_1 C13_1 C22_1 . . . 114.3(9) ?
C9_1 C13_1 H1c13_1 . . . 99.7(8) ?
C21_1 C13_1 C22_1 . . . 108.6(9) ?
C21_1 C13_1 H1c13_1 . . . 106.5(9) ?
C22_1 C13_1 H1c13_1 . . . 109.9(9) ?
C9_2 C13_2 C21_2 . . . 102.5(9) ?
C9_2 C13_2 C22_2 . . . 107.9(10) ?
C9_2 C13_2 H1c13_2 . . . 114.1(10) ?
C21_2 C13_2 C22_2 . . . 107.3(9) ?
C21_2 C13_2 H1c13_2 . . . 114.7(10) ?
C22_2 C13_2 H1c13_2 . . . 109.9(9) ?
C6_2 C14_1 C12_1 . . . 102.8(9) ?
C6_2 C14_1 C15 . . . 107.5(9) ?
C6_2 C14_1 H1c14_1 . . . 113.8(10) ?
C12_1 C14_1 C15 . . . 106.1(9) ?
C12_1 C14_1 H1c14_1 . . . 115.0(9) ?
C15 C14_1 H1c14_1 . . . 110.9(10) ?
C6_1 C14_2 C12_2 . . . 116.4(10) ?
C6_1 C14_2 C15 . . . 111.6(8) ?
C6_1 C14_2 H1c14_2 . . . 102.9(9) ?
C12_2 C14_2 C15 . . . 109.9(10) ?
C12_2 C14_2 H1c14_2 . . . 105.1(8) ?
C15 C14_2 H1c14_2 . . . 110.4(10) ?
C14_1 C15 C14_2 . . . 109.5(9) ?
C14_1 C15 H1c15 . . . 109.5(10) ?
C14_1 C15 H2c15 . . . 109.5(12) ?
C14_2 C15 H1c15 . . . 109.4(12) ?
C14_2 C15 H2c15 . . . 109.5(10) ?
H1c15 C15 H2c15 . . . 109.5(11) ?
C5_1 C16_1 C17_1 . . . 116.4(10) ?
C5_1 C16_1 C21_1 . . . 108.3(10) ?
C5_1 C16_1 H1c16_1 . . . 106.6(9) ?
C17_1 C16_1 C21_1 . . . 112.8(10) ?
C17_1 C16_1 H1c16_1 . . . 101.6(10) ?
C21_1 C16_1 H1c16_1 . . . 110.8(11) ?
C5_2 C16_2 C17_2 . . . 105.5(9) ?
C5_2 C16_2 C21_2 . . . 111.5(10) ?
C5_2 C16_2 H1c16_2 . . . 110.1(10) ?
C17_2 C16_2 C21_2 . . . 107.1(9) ?
C17_2 C16_2 H1c16_2 . . . 114.2(11) ?
C21_2 C16_2 H1c16_2 . . . 108.4(10) ?
N3_1 C17_1 C11_1 . . . 131.9(9) ?
N3_1 C17_1 C16_1 . . . 112.9(9) ?
C11_1 C17_1 C16_1 . . . 115.1(9) ?
N3_2 C17_2 C11_2 . . . 117.1(10) ?
N3_2 C17_2 C16_2 . . . 113.6(10) ?
C11_2 C17_2 C16_2 . . . 129.3(11) ?
C11_1 C18_1 C19_1 . . . 125.0(11) ?
C11_1 C18_1 H1c18_1 . . . 117.5(12) ?
C19_1 C18_1 H1c18_1 . . . 117.5(11) ?
C11_2 C18_2 C19_2 . . . 114.8(11) ?
C11_2 C18_2 H1c18_2 . . . 122.7(12) ?
C19_2 C18_2 H1c18_2 . . . 122.5(12) ?
C10_1 C19_1 C18_1 . . . 113.8(10) ?
C10_1 C19_1 C20_1 . . . 122.1(11) ?
C18_1 C19_1 C20_1 . . . 124.0(11) ?
C10_2 C19_2 C18_2 . . . 123.6(11) ?
C10_2 C19_2 N20_2 . . . 123.5(12) ?
C18_2 C19_2 N20_2 . . . 112.4(11) ?
C19_1 C20_1 C25_1 . . . 116.4(12) ?
C19_1 C20_1 H1c20_1 . . . 121.8(13) ?
C25_1 C20_1 H1c20_1 . . . 121.8(13) ?
C19_2 N20_2 C25_2 . . . 111.3(12) ?
C13_1 C21_1 C16_1 . . . 101.0(9) ?
C13_1 C21_1 H1c21_1 . . . 109.5(10) ?
C13_1 C21_1 H2c21_1 . . . 109.5(13) ?
C16_1 C21_1 H1c21_1 . . . 109.5(12) ?
C16_1 C21_1 H2c21_1 . . . 109.5(11) ?
H1c21_1 C21_1 H2c21_1 . . . 116.8(13) ?
C13_2 C21_2 C16_2 . . . 115.4(10) ?
C13_2 C21_2 H1c21_2 . . . 109.5(10) ?
C13_2 C21_2 H2c21_2 . . . 109.4(11) ?
C16_2 C21_2 H1c21_2 . . . 109.5(10) ?
C16_2 C21_2 H2c21_2 . . . 109.5(11) ?
H1c21_2 C21_2 H2c21_2 . . . 102.9(11) ?
C11_1 C22_1 C13_1 . . . 103.9(9) ?
C11_1 C22_1 H1c22_1 . . . 109.5(12) ?
C11_1 C22_1 H2c22_1 . . . 109.5(10) ?
C13_1 C22_1 H1c22_1 . . . 109.4(10) ?
C13_1 C22_1 H2c22_1 . . . 109.5(11) ?
H1c22_1 C22_1 H2c22_1 . . . 114.5(11) ?
C11_2 C22_2 C13_2 . . . 121.1(10) ?
C11_2 C22_2 H1c22_2 . . . 109.5(11) ?
C11_2 C22_2 H2c22_2 . . . 109.5(9) ?
C13_2 C22_2 H1c22_2 . . . 109.5(9) ?
C13_2 C22_2 H2c22_2 . . . 109.5(10) ?
H1c22_2 C22_2 H2c22_2 . . . 94.7(10) ?
C10_1 C23_1 C24_1 . . . 123.3(12) ?
C10_1 C23_1 O1_1 . . . 120.1(11) ?
C24_1 C23_1 O1_1 . . . 116.6(12) ?
C10_2 C23_2 N24_2 . . . 109.0(11) ?
C10_2 C23_2 H1c23_2 . . . 125.5(12) ?
N24_2 C23_2 H1c23_2 . . . 125.5(12) ?
C23_1 C24_1 C25_1 . . . 115.3(14) ?
C23_1 C24_1 H1c24_1 . . . 122.3(13) ?
C25_1 C24_1 H1c24_1 . . . 122.3(13) ?
C23_2 N24_2 C25_2 . . . 126.6(13) ?
C20_1 C25_1 C24_1 . . . 124.7(14) ?
C20_1 C25_1 H1c25_1 . . . 117.7(14) ?
C24_1 C25_1 H1c25_1 . . . 117.6(14) ?
N20_2 C25_2 N24_2 . . . 123.6(13) ?
N20_2 C25_2 H1c25_2 . . . 118.2(14) ?
N24_2 C25_2 H1c25_2 . . . 118.2(13) ?
C23_1 O1_1 C26_1 . . . 133.5(14) ?
O1_1 C26_1 H1c26_1 . . . 109.4(19) ?
O1_1 C26_1 H2c26_1 . . . 109.4(19) ?
O1_1 C26_1 H3c26_1 . . . 109.4(19) ?
H1c26_1 C26_1 H2c26_1 . . . 109(2) ?
H1c26_1 C26_1 H3c26_1 . . . 110(2) ?
H2c26_1 C26_1 H3c26_1 . . . 110(2) ?
O2 C96 C97 . . . 85(3) ?
O2 C96 H1c96 . . . 109(4) ?
O2 C96 H2c96 . . . 109(3) ?
C97 C96 H1c96 . . . 110(3) ?
C97 C96 H2c96 . . . 110(4) ?
H1c96 C96 H2c96 . . . 126(5) ?
C96 C97 H1c97 . . . 110(3) ?
C96 C97 H2c97 . . . 109(3) ?
C96 C97 H3c97 . . . 110(2) ?
H1c97 C97 H2c97 . . . 109(2) ?
H1c97 C97 H3c97 . . . 110(3) ?
H2c97 C97 H3c97 . . . 109(2) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
? ? ? ? ? ? ? ? ? ? ?


#=======================================================================

# 11. STRUCTURE-FACTOR LIST

_database_code_depnum_ccdc_archive 'CCDC 1013544'
