# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20190520_331bicyclopr_2
_database_code_depnum_ccdc_archive 'CCDC 2027731'
loop_
_audit_author_name
_audit_author_address
'Akitaka Ito'
;Kochi University of Technology
Japan
;
_audit_update_record             
;
2020-09-07 deposited with the CCDC.	2020-10-28 downloaded from the CCDC.
;
_audit_creation_date             2020-09-07
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
ito.akitaka@kochi-tech.ac.jp
_chemical_name_common            ?
_chemical_name_systematic        KUTYY-26bicycloPr
_chemical_formula_moiety         'C12 H19 N5 O4'
_chemical_formula_sum            'C12 H19 N5 O4'
_chemical_formula_weight         297.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H19 N5 O4 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   17.8252(6)
_cell_length_b                   7.4804(2)
_cell_length_c                   10.9523(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.159(4)
_cell_angle_gamma                90
_cell_volume                     1409.56(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7233
_cell_measurement_temperature    123.15
_cell_measurement_theta_max      30.0420
_cell_measurement_theta_min      2.3500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.775
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.47a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -10 3 0.1404
-25 0 6 0.0354
5 10 -3 0.1370
25 -1 -6 0.0320
9 7 -11 0.0998
24 0 0 0.0324
1 -2 -2 0.1322
2 0 1 0.0320
-2 0 -1 0.0463
-1 0 1 0.0160
1 0 -1 0.0174
-1 -1 1 0.1146
0 -1 1 0.1196
0 0 -1 0.0288
-1 -1 -2 0.0977
0 0 1 0.0174

_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.294
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.033
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.5953 -10.3589 2.7186 0.5775 0.6090 0.5436
-24.8697 -0.0107 6.1900 -0.2989 -0.3146 0.9009
4.6446 10.2149 -3.1996 -0.5444 -0.5741 -0.6116
24.8651 -0.5123 -6.0842 0.3296 0.3470 -0.8781
8.5487 7.4364 -10.6497 -0.0177 -0.6909 -0.7227
24.3003 0.1295 -0.0805 0.0157 0.5883 -0.8085
1.0000 -2.0000 -2.0000 0.2263 0.0331 0.0230
2.0000 -0.0000 1.0000 -0.0433 0.0974 -0.0532
-2.0000 0.0000 -1.0000 0.0433 -0.0974 0.0532
-1.0000 0.0000 1.0000 -0.0458 0.0235 0.0459
1.0000 -0.0000 -1.0000 0.0458 -0.0235 -0.0459
-1.0000 -1.0000 1.0000 0.0219 0.0758 0.0867
-0.0000 -1.0000 1.0000 0.0228 0.1005 0.0537
0.0000 -0.0000 -1.0000 0.0450 -0.0481 -0.0128
-1.0000 -1.0000 -2.0000 0.1569 -0.0685 0.0482
-0.0000 0.0000 1.0000 -0.0450 0.0481 0.0128

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10670
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.368
_diffrn_ambient_temperature      123.15
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  13.00   0.50   32.49    --   12.40  88.00 -84.00   52
  2  ω    -22.00  11.00   0.50   32.49    --  -13.03  57.00-180.00   66
  3  ω    -53.00  43.00   0.50   32.49    --  -13.03  88.00 -84.00  192
  4  ω    -41.00  50.00   0.50   32.49    --   12.40 -88.00 159.00  182
  5  ω    -22.00  27.00   0.50   32.49    --  -13.03 -99.00   0.00   98
  6  ω    -97.00 -50.00   0.50   32.49    --  -13.03-178.00 -60.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0008564000
_diffrn_orient_matrix_UB_12      -0.0677688000
_diffrn_orient_matrix_UB_13      -0.0449692000
_diffrn_orient_matrix_UB_21      0.0246485000
_diffrn_orient_matrix_UB_22      -0.0523405000
_diffrn_orient_matrix_UB_23      0.0481149000
_diffrn_orient_matrix_UB_31      -0.0330102000
_diffrn_orient_matrix_UB_32      -0.0408378000
_diffrn_orient_matrix_UB_33      0.0128480000
_diffrn_oxdiff_digest_frames     
;
019ef3b83a4f11bd2c3af873548cfad25d00684aed1
;
_diffrn_oxdiff_digest_hkl        
;
015b837f9e9c8718566bfb35abc4795eb7cae1
;
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              PhotonJet-S
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2478
_reflns_number_total             2885
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2885
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.053
_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)+(0.0385P)²+0.5226P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0871
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N009(H009)
2.b Ternary CH refined with riding coordinates:
 C00D(H00D), C00E(H00E)
2.c Secondary CH2 refined with riding coordinates:
 C00G(H00B,H00C), C00H(H00G,H00H), C00I(H00I,H00J), C00J(H00K,H00L)
2.d Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00F(H00F)
2.e Idealised Me refined as rotating group:
 C00K(H00M,H00N,H00O), C00L(H00P,H00Q,H00R)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O001 O 0.33583(5) 0.85769(12) 0.47639(8) 0.0220(2) Uani 1 1 d . . . . .
O002 O 0.14554(5) 0.07451(12) 0.37514(8) 0.0223(2) Uani 1 1 d . . . . .
O003 O 0.42281(5) 0.69327(12) 0.42194(9) 0.0217(2) Uani 1 1 d . . . . .
O004 O 0.06970(5) 0.25741(14) 0.24329(10) 0.0264(2) Uani 1 1 d . . . . .
N005 N 0.33551(6) 0.32660(14) 0.32576(10) 0.0155(2) Uani 1 1 d . . . . .
N006 N 0.16301(6) 0.60835(14) 0.22209(10) 0.0163(2) Uani 1 1 d . . . . .
N007 N 0.13592(6) 0.20418(14) 0.29985(10) 0.0177(2) Uani 1 1 d . . . . .
N008 N 0.35363(6) 0.73533(14) 0.41035(10) 0.0164(2) Uani 1 1 d . . . . .
N009 N 0.25703(6) 0.44938(14) 0.13820(9) 0.0157(2) Uani 1 1 d . . . . .
H009 H 0.254271 0.520763 0.073304 0.019 Uiso 1 1 d R . . . .
C00A C 0.22015(7) 0.70081(17) 0.29657(11) 0.0160(3) Uani 1 1 d . . . . .
H00A H 0.208672 0.809391 0.332896 0.019 Uiso 1 1 calc R . . . .
C00B C 0.29617(7) 0.64264(16) 0.32258(11) 0.0153(3) Uani 1 1 d . . . . .
C00C C 0.19969(7) 0.29231(16) 0.27638(11) 0.0156(3) Uani 1 1 d . . . . .
C00D C 0.18489(7) 0.43363(16) 0.17508(11) 0.0154(3) Uani 1 1 d . . . . .
H00D H 0.142535 0.393137 0.100978 0.018 Uiso 1 1 calc R . . . .
C00E C 0.31991(7) 0.49195(16) 0.24902(11) 0.0155(3) Uani 1 1 d . . . . .
H00E H 0.367344 0.526962 0.222175 0.019 Uiso 1 1 calc R . . . .
C00F C 0.27363(7) 0.23740(16) 0.33712(11) 0.0155(3) Uani 1 1 d . . . . .
H00F H 0.280429 0.133126 0.388366 0.019 Uiso 1 1 calc R . . . .
C00G C 0.41509(7) 0.25605(18) 0.37040(13) 0.0200(3) Uani 1 1 d . . . . .
H00B H 0.415401 0.156340 0.429977 0.024 Uiso 1 1 calc R . . . .
H00C H 0.449575 0.351188 0.416906 0.024 Uiso 1 1 calc R . . . .
C00H C 0.08333(7) 0.67862(19) 0.17704(13) 0.0227(3) Uani 1 1 d . . . . .
H00G H 0.075958 0.775942 0.234052 0.027 Uiso 1 1 calc R . . . .
H00H H 0.045957 0.582281 0.180972 0.027 Uiso 1 1 calc R . . . .
C00I C 0.44679(8) 0.18962(19) 0.26207(14) 0.0258(3) Uani 1 1 d . . . . .
H00I H 0.451477 0.292437 0.207627 0.031 Uiso 1 1 calc R . . . .
H00J H 0.499579 0.140559 0.297619 0.031 Uiso 1 1 calc R . . . .
C00J C 0.06574(9) 0.7498(2) 0.04230(14) 0.0331(4) Uani 1 1 d . . . . .
H00K H 0.074089 0.652758 -0.014175 0.040 Uiso 1 1 calc R . . . .
H00L H 0.010260 0.784502 0.014826 0.040 Uiso 1 1 calc R . . . .
C00K C 0.39671(9) 0.0470(2) 0.18091(14) 0.0308(3) Uani 1 1 d . . . . .
H00M H 0.422183 0.004539 0.117159 0.046 Uiso 1 1 calc GR . . . .
H00N H 0.345849 0.097733 0.138707 0.046 Uiso 1 1 calc GR . . . .
H00O H 0.389796 -0.053267 0.234536 0.046 Uiso 1 1 calc GR . . . .
C00L C 0.11509(11) 0.9093(2) 0.02720(15) 0.0425(4) Uani 1 1 d . . . . .
H00P H 0.098804 0.952397 -0.060264 0.064 Uiso 1 1 calc GR . . . .
H00Q H 0.169864 0.873655 0.047423 0.064 Uiso 1 1 calc GR . . . .
H00R H 0.108482 1.004898 0.084687 0.064 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O001 N008 1.2576(13) . ?
O002 N007 1.2555(14) . ?
O003 N008 1.2465(13) . ?
O004 N007 1.2463(14) . ?
N005 C00E 1.4803(15) . ?
N005 C00F 1.3226(16) . ?
N005 C00G 1.4720(16) . ?
N006 C00A 1.3215(16) . ?
N006 C00D 1.4935(16) . ?
N006 C00H 1.4733(16) . ?
N007 C00C 1.3947(16) . ?
N008 C00B 1.3925(16) . ?
N009 C00D 1.4498(15) . ?
N009 C00E 1.4558(16) . ?
C00A C00B 1.3803(17) . ?
C00B C00E 1.5090(17) . ?
C00C C00D 1.5051(17) . ?
C00C C00F 1.3748(17) . ?
C00G C00I 1.5248(19) . ?
C00H C00J 1.522(2) . ?
C00I C00K 1.520(2) . ?
C00J C00L 1.517(3) . ?

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
C00F N005 C00E 115.94(10) . . ?
C00F N005 C00G 122.87(11) . . ?
C00G N005 C00E 120.65(10) . . ?
C00A N006 C00D 116.24(10) . . ?
C00A N006 C00H 122.68(11) . . ?
C00H N006 C00D 120.84(10) . . ?
O002 N007 C00C 120.55(10) . . ?
O004 N007 O002 121.48(10) . . ?
O004 N007 C00C 117.97(11) . . ?
O001 N008 C00B 120.58(10) . . ?
O003 N008 O001 121.12(10) . . ?
O003 N008 C00B 118.30(10) . . ?
C00D N009 C00E 109.34(9) . . ?
N006 C00A C00B 121.27(11) . . ?
N008 C00B C00E 118.83(10) . . ?
C00A C00B N008 119.39(11) . . ?
C00A C00B C00E 121.50(11) . . ?
N007 C00C C00D 118.28(10) . . ?
C00F C00C N007 119.60(11) . . ?
C00F C00C C00D 121.84(11) . . ?
N006 C00D C00C 111.82(9) . . ?
N009 C00D N006 110.83(10) . . ?
N009 C00D C00C 105.38(10) . . ?
N005 C00E C00B 111.00(9) . . ?
N009 C00E N005 106.26(10) . . ?
N009 C00E C00B 110.26(10) . . ?
N005 C00F C00C 121.43(11) . . ?
N005 C00G C00I 112.30(11) . . ?
N006 C00H C00J 112.69(11) . . ?
C00K C00I C00G 113.78(11) . . ?
C00L C00J C00H 113.74(12) . . ?

_olex2_date_sample_data_collection 2019-05-20
_olex2_submission_original_sample_id KUTYY-26bicycloPr
_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 1.084
_oxdiff_exptl_absorpt_empirical_full_min 0.815
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_331bicyclo-bn_1
_database_code_depnum_ccdc_archive 'CCDC 2027735'
loop_
_audit_author_name
_audit_author_address
'Akitaka Ito'
;Kochi University of Technology
Japan
;
_audit_update_record             
;
2020-09-07 deposited with the CCDC.	2020-10-28 downloaded from the CCDC.
;
_audit_creation_date             2020-09-07
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        KUTYY-29bicycloBn
_chemical_formula_moiety         'C20 H19 N5 O4'
_chemical_formula_sum            'C20 H19 N5 O4'
_chemical_formula_weight         393.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C84 H72 N16 O16 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.4032(16)
_cell_length_b                   9.8582(2)
_cell_length_c                   19.916(2)
_cell_angle_alpha                90
_cell_angle_beta                 140.02(2)
_cell_angle_gamma                90
_cell_volume                     1817.0(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7839
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      29.4150
_cell_measurement_theta_min      2.0810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.141
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.47a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 3 0.3866
1 0 -3 0.4028
2 1 -1 0.2631
-2 -1 1 0.2218
-1 2 1 0.2369
1 -2 -1 0.2506
2 -1 0 0.2563
2 -2 -1 0.2247
-2 1 0 0.3022
1 1 1 0.3162
0 1 1 0.2797
1 -1 -1 0.2389
2 -1 -1 0.2639
-2 1 2 0.3522
2 -1 -2 0.2976
1 -2 -3 0.2932
2 -2 -3 0.2864
1 -1 -2 0.3098
-1 1 2 0.3610
-2 -1 3 0.2935
2 1 -4 0.3521
2 1 -3 0.3283
0 0 1 0.3490
-1 -1 0 0.2405
1 1 0 0.2483
-1 -1 2 0.2002
1 1 -2 0.2701
-2 -2 1 0.2135
1 1 -1 0.2440
0 0 -1 0.4096
-1 -2 2 0.1949
1 2 -3 0.2541
0 -1 1 0.1688
0 1 -1 0.2446
-1 14 1 0.2477

_exptl_crystal_size_max          0.796
_exptl_crystal_size_mid          0.532
_exptl_crystal_size_min          0.413
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0000 0.0000 3.0000 0.0469 0.0838 0.0691
1.0000 -0.0000 -3.0000 -0.0469 -0.0838 -0.0691
2.0000 1.0000 -1.0000 -0.0406 -0.0538 0.1191
-2.0000 -1.0000 1.0000 0.0406 0.0538 -0.1191
-1.0000 2.0000 1.0000 0.1190 -0.0816 0.0482
1.0000 -2.0000 -1.0000 -0.1190 0.0816 -0.0482
2.0000 -1.0000 0.0000 -0.1156 0.0789 0.0954
2.0000 -2.0000 -1.0000 -0.1573 0.0961 0.0166
-2.0000 1.0000 -0.0000 0.1156 -0.0789 -0.0954
1.0000 1.0000 1.0000 0.0034 -0.0027 0.1435
0.0000 1.0000 1.0000 0.0418 -0.0172 0.0788
1.0000 -1.0000 -1.0000 -0.0801 0.0317 -0.0140
2.0000 -1.0000 -1.0000 -0.1184 0.0462 0.0507
-2.0000 1.0000 2.0000 0.1213 -0.0134 -0.0061
2.0000 -1.0000 -2.0000 -0.1213 0.0134 0.0061
1.0000 -2.0000 -3.0000 -0.1247 0.0161 -0.1374
2.0000 -2.0000 -3.0000 -0.1630 0.0306 -0.0726
1.0000 -1.0000 -2.0000 -0.0829 -0.0011 -0.0586
-1.0000 1.0000 2.0000 0.0829 0.0011 0.0586
-2.0000 -1.0000 3.0000 0.0463 0.1193 -0.0299
2.0000 1.0000 -4.0000 -0.0492 -0.1520 -0.0148
2.0000 1.0000 -3.0000 -0.0463 -0.1193 0.0299
-0.0000 0.0000 1.0000 0.0029 0.0328 0.0446
-1.0000 -1.0000 0.0000 -0.0006 0.0355 -0.0989
1.0000 1.0000 -0.0000 0.0006 -0.0355 0.0989
-1.0000 -1.0000 2.0000 0.0051 0.1010 -0.0097
1.0000 1.0000 -2.0000 -0.0051 -0.1010 0.0097
-2.0000 -2.0000 1.0000 0.0017 0.1037 -0.1532
1.0000 1.0000 -1.0000 -0.0023 -0.0682 0.0543
0.0000 -0.0000 -1.0000 -0.0029 -0.0328 -0.0446
-1.0000 -2.0000 2.0000 -0.0338 0.1510 -0.0439
1.0000 2.0000 -3.0000 0.0309 -0.1837 -0.0007
-0.0000 -1.0000 1.0000 -0.0361 0.0827 0.0104
0.0000 1.0000 -1.0000 0.0361 -0.0827 -0.0104
-0.6976 13.8872 1.1047 0.5702 -0.6677 0.4786

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13775
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.505
_diffrn_ambient_temperature      93.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  18.00   0.50    0.75    --   12.56 -84.00  67.00   74
  2  ω    -51.00  33.00   0.50    0.75    --  -13.19  84.00-172.00  168
  3  ω    -41.00  11.00   0.50    0.75    --  -13.19 -84.00  67.00  104
  4  ω     43.00  95.00   0.50    0.75    --   12.56 178.00  30.00  104
  5  ω     32.00  58.00   0.50    0.75    --   12.56 -99.00 -30.00   52
  6  ω    -21.00   7.00   0.50    0.75    --   12.56 -99.00 -30.00   56
  7  ω     29.00  62.00   0.50    0.75    --  -13.19  57.00-150.00   66
  8  ω    -18.00   7.00   0.50    0.75    --  -13.19 -99.00   0.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0383338000
_diffrn_orient_matrix_UB_12      0.0389060000
_diffrn_orient_matrix_UB_13      0.0028519000
_diffrn_orient_matrix_UB_21      0.0144884000
_diffrn_orient_matrix_UB_22      -0.0499615000
_diffrn_orient_matrix_UB_23      0.0327659000
_diffrn_orient_matrix_UB_31      0.0647598000
_diffrn_orient_matrix_UB_32      0.0341646000
_diffrn_orient_matrix_UB_33      0.0446114000
_diffrn_oxdiff_digest_frames     
;
018612716535303438e226bcc075b0c9540067411be
;
_diffrn_oxdiff_digest_hkl        
;
01caa2c90eeee073f53e5c657f8ce707435be4
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3308
_reflns_number_total             3711
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0089(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3711
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.057
_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)+(0.0376P)²+0.7655P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0892
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C00B(H00C), C00C(H00D)
2.b Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00I(H00G,H00I)
2.c Aromatic/amide H refined with riding coordinates:
 N008(H008), C00E(H00E), C00F(H00F), C00H(H00H), C00J(H00J), C00L(H00L),
 C00M(H00M), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O001 O 0.42248(10) 0.57844(9) 0.87150(7) 0.0209(2) Uani 1 1 d . . . . .
O002 O 0.31749(10) 0.38641(9) 0.83683(7) 0.0211(2) Uani 1 1 d . . . . .
O003 O 0.00340(11) 0.66585(10) 0.35924(8) 0.0299(3) Uani 1 1 d . . . . .
O004 O 0.04344(10) 0.45237(9) 0.36052(7) 0.0222(2) Uani 1 1 d . . . . .
N005 N 0.36058(11) 0.47203(10) 0.81924(8) 0.0151(2) Uani 1 1 d . . . . .
N006 N 0.42757(11) 0.48138(10) 0.67685(8) 0.0126(2) Uani 1 1 d . . . . .
N007 N 0.23523(11) 0.32861(10) 0.59294(8) 0.0147(2) Uani 1 1 d . . . . .
N008 N 0.32052(11) 0.67501(10) 0.67229(8) 0.0157(2) Uani 1 1 d . . . . .
H008 H 0.339299 0.749130 0.705720 0.019 Uiso 1 1 calc R . . . .
N009 N 0.07146(12) 0.55906(11) 0.40689(8) 0.0179(2) Uani 1 1 d . . . . .
C00A C 0.50434(13) 0.56452(12) 0.66966(10) 0.0150(3) Uani 1 1 d . . . . .
H00A H 0.579563 0.618178 0.734668 0.018 Uiso 1 1 calc R . . . .
H00B H 0.435119 0.629110 0.610952 0.018 Uiso 1 1 calc R . . . .
C00B C 0.28467(13) 0.43666(12) 0.57426(9) 0.0132(2) Uani 1 1 d . . . . .
H00C H 0.294180 0.398267 0.533266 0.016 Uiso 1 1 calc R . . . .
C00C C 0.40959(13) 0.55194(12) 0.73070(9) 0.0137(3) Uani 1 1 d . . . . .
H00D H 0.506626 0.578307 0.802294 0.016 Uiso 1 1 calc R . . . .
C00D C 0.34068(13) 0.45199(12) 0.73949(9) 0.0143(3) Uani 1 1 d . . . . .
C00E C 0.21564(14) 0.13415(13) 0.43862(10) 0.0186(3) Uani 1 1 d . . . . .
H00E H 0.144254 0.193078 0.381060 0.022 Uiso 1 1 calc R . . . .
C00F C 0.26328(13) 0.34329(12) 0.67339(9) 0.0149(3) Uani 1 1 d . . . . .
H00F H 0.229101 0.277276 0.685348 0.018 Uiso 1 1 calc R . . . .
C00G C 0.57499(13) 0.48310(13) 0.65337(9) 0.0149(3) Uani 1 1 d . . . . .
C00H C 0.58342(13) 0.34246(13) 0.65825(10) 0.0171(3) Uani 1 1 d . . . . .
H00H H 0.543292 0.292436 0.672267 0.021 Uiso 1 1 calc R . . . .
C00I C 0.14913(14) 0.21533(12) 0.51806(10) 0.0173(3) Uani 1 1 d . . . . .
H00G H 0.064382 0.251983 0.446786 0.021 Uiso 1 1 calc R . . . .
H00I H 0.113183 0.158770 0.535669 0.021 Uiso 1 1 calc R . . . .
C00J C 0.63672(14) 0.55512(14) 0.63433(10) 0.0184(3) Uani 1 1 d . . . . .
H00J H 0.631006 0.651327 0.630442 0.022 Uiso 1 1 calc R . . . .
C00K C 0.18441(13) 0.55711(12) 0.51658(9) 0.0151(3) Uani 1 1 d . . . . .
C00L C 0.21232(14) 0.67197(12) 0.56915(10) 0.0163(3) Uani 1 1 d . . . . .
H00L H 0.153088 0.749883 0.530807 0.020 Uiso 1 1 calc R . . . .
C00M C 0.65050(14) 0.27456(14) 0.64266(10) 0.0204(3) Uani 1 1 d . . . . .
H00M H 0.654060 0.178250 0.644602 0.024 Uiso 1 1 calc R . . . .
C00N C 0.23727(14) 0.12847(12) 0.51981(10) 0.0169(3) Uani 1 1 d . . . . .
C00O C 0.29809(15) 0.05393(14) 0.44149(11) 0.0229(3) Uani 1 1 d . . . . .
H00O H 0.282967 0.058209 0.385979 0.028 Uiso 1 1 calc R . . . .
C00P C 0.71228(14) 0.34665(14) 0.62430(10) 0.0224(3) Uani 1 1 d . . . . .
H00P H 0.758370 0.300015 0.614008 0.027 Uiso 1 1 calc R . . . .
C00Q C 0.34263(15) 0.04191(13) 0.60396(10) 0.0223(3) Uani 1 1 d . . . . .
H00Q H 0.358298 0.037595 0.659735 0.027 Uiso 1 1 calc R . . . .
C00R C 0.70618(15) 0.48739(14) 0.62108(10) 0.0222(3) Uani 1 1 d . . . . .
H00R H 0.749701 0.537353 0.609780 0.027 Uiso 1 1 calc R . . . .
C00S C 0.40230(16) -0.03225(14) 0.52530(11) 0.0256(3) Uani 1 1 d . . . . .
H00S H 0.458364 -0.087367 0.527176 0.031 Uiso 1 1 calc R . . . .
C00T C 0.42456(16) -0.03779(14) 0.60666(11) 0.0264(3) Uani 1 1 d . . . . .
H00T H 0.496269 -0.096517 0.664288 0.032 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O001 N005 1.2476(14) . ?
O002 N005 1.2463(13) . ?
O003 N009 1.2426(14) . ?
O004 N009 1.2453(14) . ?
N005 C00D 1.3951(15) . ?
N006 C00A 1.4688(15) . ?
N006 C00B 1.4698(17) . ?
N006 C00C 1.4583(15) . ?
N007 C00B 1.4786(15) . ?
N007 C00F 1.3262(16) . ?
N007 C00I 1.4747(16) . ?
N008 C00C 1.4777(15) . ?
N008 C00L 1.3202(17) . ?
N009 C00K 1.4046(17) . ?
C00A C00G 1.5136(16) . ?
C00B C00K 1.5076(17) . ?
C00C C00D 1.5011(16) . ?
C00D C00F 1.3693(18) . ?
C00E C00N 1.3938(17) . ?
C00E C00O 1.3910(18) . ?
C00G C00H 1.3887(18) . ?
C00G C00J 1.3983(17) . ?
C00H C00M 1.3919(18) . ?
C00I C00N 1.5095(17) . ?
C00J C00R 1.3859(18) . ?
C00K C00L 1.3765(17) . ?
C00M C00P 1.3891(19) . ?
C00N C00Q 1.3936(19) . ?
C00O C00S 1.386(2) . ?
C00P C00R 1.389(2) . ?
C00Q C00T 1.384(2) . ?
C00S C00T 1.391(2) . ?

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
O001 N005 C00D 117.45(10) . . ?
O002 N005 O001 121.77(10) . . ?
O002 N005 C00D 120.79(10) . . ?
C00A N006 C00B 112.88(9) . . ?
C00C N006 C00A 112.13(9) . . ?
C00C N006 C00B 108.47(9) . . ?
C00F N007 C00B 117.76(10) . . ?
C00F N007 C00I 123.09(10) . . ?
C00I N007 C00B 119.01(9) . . ?
C00L N008 C00C 118.94(10) . . ?
O003 N009 O004 122.10(11) . . ?
O003 N009 C00K 119.68(11) . . ?
O004 N009 C00K 118.22(10) . . ?
N006 C00A C00G 113.89(10) . . ?
N006 C00B N007 107.32(9) . . ?
N006 C00B C00K 109.05(10) . . ?
N007 C00B C00K 113.22(10) . . ?
N006 C00C N008 110.42(9) . . ?
N006 C00C C00D 106.18(9) . . ?
N008 C00C C00D 112.21(10) . . ?
N005 C00D C00C 117.55(10) . . ?
C00F C00D N005 120.74(11) . . ?
C00F C00D C00C 121.69(11) . . ?
C00O C00E C00N 120.31(12) . . ?
N007 C00F C00D 121.13(11) . . ?
C00H C00G C00A 123.47(11) . . ?
C00H C00G C00J 119.09(11) . . ?
C00J C00G C00A 117.42(11) . . ?
C00G C00H C00M 120.19(12) . . ?
N007 C00I C00N 111.44(10) . . ?
C00R C00J C00G 120.58(12) . . ?
N009 C00K C00B 119.18(11) . . ?
C00L C00K N009 119.13(11) . . ?
C00L C00K C00B 121.16(11) . . ?
N008 C00L C00K 120.70(11) . . ?
C00P C00M C00H 120.45(12) . . ?
C00E C00N C00I 120.93(12) . . ?
C00Q C00N C00E 119.29(12) . . ?
C00Q C00N C00I 119.78(11) . . ?
C00S C00O C00E 120.04(12) . . ?
C00R C00P C00M 119.52(12) . . ?
C00T C00Q C00N 120.31(12) . . ?
C00J C00R C00P 120.14(12) . . ?
C00O C00S C00T 119.81(13) . . ?
C00Q C00T C00S 120.25(13) . . ?

_olex2_date_sample_data_collection 2019-11-07
_olex2_submission_original_sample_id KUTYY-29bicycloBn
_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 1.092
_oxdiff_exptl_absorpt_empirical_full_min 0.927
