# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_exp_151_auto
_database_code_depnum_ccdc_archive 'CCDC 2310475'
loop_
_audit_author_name
_audit_author_address
'Ryohei Fujita'
;Waseda University
Japan
;
_audit_update_record             
;
2023-11-25 deposited with the CCDC.	2024-02-01 downloaded from the CCDC.
;
_audit_creation_date             2023-07-26
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        'cyanodecalin 151'
_chemical_formula_moiety         'C15 H23 N O'
_chemical_formula_sum            'C15 H23 N O'
_chemical_formula_weight         233.34
_chemical_melting_point          398-399
_chemical_oxdiff_formula         'C15 H23 N O'
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'

_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        P21/c
_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                   10.25850(10)
_cell_length_b                   13.8145(2)
_cell_length_c                   10.04020(10)
_cell_angle_alpha                90
_cell_angle_beta                 107.3680(10)
_cell_angle_gamma                90
_cell_volume                     1357.99(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11134
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.3790
_cell_measurement_theta_min      4.5120
_shelx_estimated_absorpt_T_max   0.909
_shelx_estimated_absorpt_T_min   0.773
_exptl_absorpt_coefficient_mu    0.542
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.316
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -8 3 0.2505
-6 -1 1 0.0916
7 1 -1 0.1085
1 -9 0 0.2320
0 0 -6 0.0733
-1 9 1 0.2563
0 1 6 0.1035
-1 -9 1 0.2308
5 -1 -6 0.1202
2 9 -1 0.2402
-5 1 6 0.0955

_exptl_crystal_size_max          0.498
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.18
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
-1.2526 -7.6610 3.3813 0.7176 -0.2498 0.6501
-6.4998 -0.8359 0.6812 0.5211 0.8534 0.0113
6.5029 0.8089 -0.6877 -0.5211 -0.8535 -0.0082
0.9792 -8.8499 0.1409 0.2485 -0.2408 0.9382
0.0040 -0.3996 -6.2146 -0.6886 0.6494 0.3228
-0.9756 8.8605 0.5998 -0.1654 0.1625 -0.9727
-0.0162 0.5098 6.2143 0.6856 -0.6465 -0.3345
-1.2650 -8.7992 0.6173 0.4443 0.0317 0.8953
4.7138 -0.5282 -5.7538 -0.9339 -0.0765 0.3493
1.9087 8.5017 -1.4263 -0.5670 -0.0419 -0.8227
-4.6825 0.8507 5.7495 0.9206 0.0756 -0.3830

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17558
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.769
_diffrn_reflns_theta_min         4.516
_diffrn_ambient_temperature      100
_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 0.945
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    103.00 177.00   0.50    0.08    --  108.01 125.00 150.00  148
  2  ω    143.00 169.00   0.50    0.08    --  108.01  24.00-114.00   52
  3  ω     87.00 133.00   0.50    0.08    --  108.01  24.00-114.00   92
  4  ω     16.00  62.00   0.50    0.05    --   43.18  24.00-114.00   92
  5  ω   -108.00 -82.00   0.50    0.05    --  -43.18 -24.00  81.00   52
  6  ω   -117.00 -81.00   0.50    0.05    --  -43.18 -77.00   0.00   72
  7  ω    -72.00 -18.00   0.50    0.05    --  -43.18 -77.00   0.00  108
  8  ω    -58.00 -19.00   0.50    0.05    --  -43.18 -77.00 -60.00   78
  9  ω   -116.00 -64.00   0.50    0.05    --  -43.18 -77.00 -60.00  104
 10  ω   -114.00 -69.00   0.50    0.05    --  -43.18 -57.00 -90.00   90
 11  ω    -51.00 -26.00   0.50    0.05    --  -43.18 -57.00 -90.00   50
 12  ω    -84.00 -21.00   0.50    0.05    --  -43.18 -38.00   0.00  126
 13  ω    -42.00 -17.00   0.50    0.05    --  -43.18 -24.00  81.00   50
 14  ω    -79.00 -17.00   0.50    0.05    --  -43.18 125.00 -60.00  124
 15  ω    -73.00 -48.00   0.50    0.08    --  -96.00  61.00  30.00   50
 16  ω    -73.00 -23.00   0.50    0.08    --  -96.00  61.00 150.00  100
 17  ω    -71.00 -22.00   0.50    0.08    --  -96.00  61.00   0.00   98
 18  ω    -67.00 -26.00   0.50    0.08    --  -96.00  61.00 -30.00   82
 19  ω    -49.00 -22.00   0.50    0.08    --  -96.00  45.00 -60.00   54
 20  ω    -19.00   6.00   0.50    0.05    --  -43.18  24.00-114.00   50
 21  ω    -64.00 -23.00   0.50    0.08    --  -96.00   0.00 -60.00   82
 22  ω    -92.00 -67.00   0.50    0.08    --  -96.00 -77.00  30.00   50
 23  ω    -93.00 -67.00   0.50    0.08    --  -96.00 -77.00 -14.53   52
 24  ω    -93.00 -67.00   0.50    0.08    --  -96.00 -77.00 -30.00   52
 25  ω    -92.00 -67.00   0.50    0.08    --  -96.00 -77.00   0.00   50
 26  ω    -94.00 -68.00   0.50    0.08    --  -96.00 -77.00  60.00   52
 27  ω    -92.00 -67.00   0.50    0.08    --  -96.00 -76.00  49.23   50
 28  ω    -94.00 -69.00   0.50    0.08    --  -96.00 -75.00  42.76   50
 29  ω   -170.00-100.00   0.50    0.08    --  -96.00 -77.00  30.00  140
 30  ω   -129.00-104.00   0.50    0.08    --  -96.00 -76.00 -35.02   50
 31  ω    -95.00 -70.00   0.50    0.08    --  -96.00 -73.00 -44.15   50
 32  ω    -94.00 -67.00   0.50    0.08    --  -96.00 -76.00 -35.02   54
 33  ω    -96.00 -70.00   0.50    0.08    --  -96.00 -75.00 -22.70   52
 34  ω    -95.00 -69.00   0.50    0.08    --  -96.00 -73.00  -1.78   52
 35  ω    -95.00 -69.00   0.50    0.08    --  -96.00 -75.00   9.83   52
 36  ω    -94.00 -69.00   0.50    0.08    --  -96.00 -71.00  12.74   50
 37  ω   -100.00 -75.00   0.50    0.08    --  -96.00 -61.00  60.00   50
 38  ω   -147.00-120.00   0.50    0.08    --  -96.00 -71.00  12.74   54
 39  ω   -167.00-141.00   0.50    0.08    --  -96.00 -61.00  60.00   52
 40  ω   -170.00 -70.00   0.50    0.08    --  -96.00 -72.00 -48.95  200
 41  ω   -169.00 -71.00   0.50    0.08    --  -96.00 -66.00 -70.32  196
 42  ω   -166.00-103.00   0.50    0.08    --  -96.00 -61.00 -30.00  126
 43  ω    -97.00 -72.00   0.50    0.08    --  -96.00 -61.00 -30.00   50
 44  ω   -104.00 -79.00   0.50    0.08    --  -96.00 -45.00   0.00   50
 45  ω   -166.00 -75.00   0.50    0.08    --  -96.00 -56.00  42.12  182
 46  ω   -123.00 -80.00   0.50    0.08    --  -96.00 -24.00  81.00   86
 47  ω    -30.00  23.00   0.50    0.05    --   43.18 -24.00  81.00  106
 48  ω     37.00  73.00   0.50    0.08    --  108.01 -61.00 120.00   72
 49  ω     37.00  80.00   0.50    0.08    --  108.01-125.00  90.00   86
 50  ω     36.00  86.00   0.50    0.05    --   43.18-125.00 -30.00  100
 51  ω     61.00 102.00   0.50    0.08    --  108.01 -95.00 -30.00   82
 52  ω     34.00  71.00   0.50    0.08    --  108.01 -61.00-180.00   74
;
_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      -0.0640436000
_diffrn_orient_matrix_UB_12      -0.0333669000
_diffrn_orient_matrix_UB_13      0.1129035000
_diffrn_orient_matrix_UB_21      -0.1435693000
_diffrn_orient_matrix_UB_22      0.0096533000
_diffrn_orient_matrix_UB_23      -0.1052045000
_diffrn_orient_matrix_UB_31      0.0071500000
_diffrn_orient_matrix_UB_32      -0.1059418000
_diffrn_orient_matrix_UB_33      -0.0451209000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2468
_reflns_number_total             2635
_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 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2635
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0374
_refine_ls_restrained_S_all      1.075
_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)+(0.0573P)²+0.3372P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1051
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C005(H005), C006(H006), C007(H007), C008(H008)
2.b Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00B(H00C,H00D), C00C(H00E,H00F), C00E(H00J,H00K), C00G(H00O,
 H00P)
2.c Idealised Me refined as rotating group:
 C00D(H00G,H00H,H00I), C00F(H00L,H00M,H00N), C00H(H00Q,H00R,H00S)
;
_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 -0.27329(7) -0.80174(5) -0.55413(8) 0.0247(2) Uani 1 1 d . . . . .
N002 N -0.52422(9) -0.66964(6) -0.46428(9) 0.0233(2) Uani 1 1 d . . . . .
C003 C -0.50577(10) -0.67721(7) -0.57072(10) 0.0175(2) Uani 1 1 d . . . . .
C004 C -0.24605(10) -0.74604(7) -0.63588(10) 0.0191(2) Uani 1 1 d . . . . .
C005 C -0.49317(9) -0.68654(7) -0.71253(10) 0.0158(2) Uani 1 1 d . . . . .
H005 H -0.5219 -0.7523 -0.7448 0.019 Uiso 1 1 calc R U . . .
C006 C -0.34695(10) -0.67310(7) -0.72097(10) 0.0164(2) Uani 1 1 d . . . . .
H006 H -0.3525 -0.6864 -0.8184 0.020 Uiso 1 1 calc R U . . .
C007 C -0.59230(9) -0.61554(7) -0.81356(10) 0.0169(2) Uani 1 1 d . . . . .
H007 H -0.5920 -0.6322 -0.9084 0.020 Uiso 1 1 calc R U . . .
C008 C -0.74073(10) -0.62582(7) -0.80922(10) 0.0193(2) Uani 1 1 d . . . . .
H008 H -0.7440 -0.6030 -0.7179 0.023 Uiso 1 1 calc R U . . .
C009 C -0.28894(10) -0.56847(7) -0.69194(10) 0.0187(2) Uani 1 1 d . . . . .
C00A C -0.39189(10) -0.50079(7) -0.79146(11) 0.0214(2) Uani 1 1 d . . . . .
H00A H -0.3628 -0.4344 -0.7692 0.026 Uiso 1 1 calc R U . . .
H00B H -0.3908 -0.5134 -0.8862 0.026 Uiso 1 1 calc R U . . .
C00B C -0.53856(10) -0.51170(7) -0.78518(11) 0.0200(2) Uani 1 1 d . . . . .
H00C H -0.5977 -0.4688 -0.8534 0.024 Uiso 1 1 calc R U . . .
H00D H -0.5421 -0.4920 -0.6936 0.024 Uiso 1 1 calc R U . . .
C00C C -0.15205(10) -0.56674(8) -0.72598(11) 0.0229(2) Uani 1 1 d . . . . .
H00E H -0.1688 -0.5807 -0.8244 0.027 Uiso 1 1 calc R U . . .
H00F H -0.1132 -0.5023 -0.7084 0.027 Uiso 1 1 calc R U . . .
C00D C -0.78943(11) -0.73121(8) -0.82584(12) 0.0249(2) Uani 1 1 d . . . . .
H00G H -0.7733 -0.7586 -0.9074 0.037 Uiso 1 1 calc R U . . .
H00H H -0.8854 -0.7335 -0.8355 0.037 Uiso 1 1 calc R U . . .
H00I H -0.7402 -0.7676 -0.7450 0.037 Uiso 1 1 calc R U . . .
C00E C -0.10776(10) -0.74292(8) -0.66028(12) 0.0254(3) Uani 1 1 d . . . . .
H00J H -0.1162 -0.7647 -0.7543 0.030 Uiso 1 1 calc R U . . .
H00K H -0.0458 -0.7864 -0.5956 0.030 Uiso 1 1 calc R U . . .
C00F C -0.26533(10) -0.53682(8) -0.53980(10) 0.0217(2) Uani 1 1 d . . . . .
H00L H -0.3518 -0.5261 -0.5235 0.033 Uiso 1 1 calc R U . . .
H00M H -0.2131 -0.4780 -0.5226 0.033 Uiso 1 1 calc R U . . .
H00N H -0.2164 -0.5866 -0.4782 0.033 Uiso 1 1 calc R U . . .
C00G C -0.04905(10) -0.63974(8) -0.64014(11) 0.0256(3) Uani 1 1 d . . . . .
H00O H -0.0251 -0.6224 -0.5422 0.031 Uiso 1 1 calc R U . . .
H00P H 0.0335 -0.6376 -0.6683 0.031 Uiso 1 1 calc R U . . .
C00H C -0.83876(11) -0.56351(8) -0.92111(13) 0.0290(3) Uani 1 1 d . . . . .
H00Q H -0.8132 -0.4967 -0.9055 0.044 Uiso 1 1 calc R U . . .
H00R H -0.9302 -0.5720 -0.9165 0.044 Uiso 1 1 calc R U . . .
H00S H -0.8344 -0.5827 -1.0116 0.044 Uiso 1 1 calc R U . . .


_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 C004 1.2168(13) . ?
N002 C003 1.1444(13) . ?
C003 C005 1.4733(13) . ?
C004 C006 1.5129(13) . ?
C004 C00E 1.5106(14) . ?
C005 H005 0.9800 . ?
C005 C006 1.5387(13) . ?
C005 C007 1.5521(13) . ?
C006 H006 0.9800 . ?
C006 C009 1.5571(13) . ?
C007 H007 0.9800 . ?
C007 C008 1.5428(13) . ?
C007 C00B 1.5326(13) . ?
C008 H008 0.9800 . ?
C008 C00D 1.5320(14) . ?
C008 C00H 1.5296(14) . ?
C009 C00A 1.5355(13) . ?
C009 C00C 1.5414(13) . ?
C009 C00F 1.5370(13) . ?
C00A H00A 0.9700 . ?
C00A H00B 0.9700 . ?
C00A C00B 1.5320(14) . ?
C00B H00C 0.9700 . ?
C00B H00D 0.9700 . ?
C00C H00E 0.9700 . ?
C00C H00F 0.9700 . ?
C00C C00G 1.5273(15) . ?
C00D H00G 0.9600 . ?
C00D H00H 0.9600 . ?
C00D H00I 0.9600 . ?
C00E H00J 0.9700 . ?
C00E H00K 0.9700 . ?
C00E C00G 1.5371(15) . ?
C00F H00L 0.9600 . ?
C00F H00M 0.9600 . ?
C00F H00N 0.9600 . ?
C00G H00O 0.9700 . ?
C00G H00P 0.9700 . ?
C00H H00Q 0.9600 . ?
C00H H00R 0.9600 . ?
C00H H00S 0.9600 . ?

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
N002 C003 C005 175.71(10) . . ?
O001 C004 C006 123.09(9) . . ?
O001 C004 C00E 122.91(9) . . ?
C00E C004 C006 114.00(8) . . ?
C003 C005 H005 107.2 . . ?
C003 C005 C006 114.26(8) . . ?
C003 C005 C007 110.30(8) . . ?
C006 C005 H005 107.2 . . ?
C006 C005 C007 110.31(7) . . ?
C007 C005 H005 107.2 . . ?
C004 C006 C005 113.73(8) . . ?
C004 C006 H006 105.4 . . ?
C004 C006 C009 110.72(8) . . ?
C005 C006 H006 105.4 . . ?
C005 C006 C009 115.22(8) . . ?
C009 C006 H006 105.4 . . ?
C005 C007 H007 107.2 . . ?
C008 C007 C005 112.52(8) . . ?
C008 C007 H007 107.2 . . ?
C00B C007 C005 109.93(8) . . ?
C00B C007 H007 107.2 . . ?
C00B C007 C008 112.59(8) . . ?
C007 C008 H008 107.9 . . ?
C00D C008 C007 112.14(8) . . ?
C00D C008 H008 107.9 . . ?
C00H C008 C007 111.44(8) . . ?
C00H C008 H008 107.9 . . ?
C00H C008 C00D 109.47(8) . . ?
C00A C009 C006 107.05(8) . . ?
C00A C009 C00C 109.97(8) . . ?
C00A C009 C00F 110.32(8) . . ?
C00C C009 C006 107.19(8) . . ?
C00F C009 C006 112.84(8) . . ?
C00F C009 C00C 109.40(8) . . ?
C009 C00A H00A 108.8 . . ?
C009 C00A H00B 108.8 . . ?
H00A C00A H00B 107.7 . . ?
C00B C00A C009 113.99(8) . . ?
C00B C00A H00A 108.8 . . ?
C00B C00A H00B 108.8 . . ?
C007 C00B H00C 109.0 . . ?
C007 C00B H00D 109.0 . . ?
C00A C00B C007 112.80(8) . . ?
C00A C00B H00C 109.0 . . ?
C00A C00B H00D 109.0 . . ?
H00C C00B H00D 107.8 . . ?
C009 C00C H00E 109.0 . . ?
C009 C00C H00F 109.0 . . ?
H00E C00C H00F 107.8 . . ?
C00G C00C C009 112.79(8) . . ?
C00G C00C H00E 109.0 . . ?
C00G C00C H00F 109.0 . . ?
C008 C00D H00G 109.5 . . ?
C008 C00D H00H 109.5 . . ?
C008 C00D H00I 109.5 . . ?
H00G C00D H00H 109.5 . . ?
H00G C00D H00I 109.5 . . ?
H00H C00D H00I 109.5 . . ?
C004 C00E H00J 109.5 . . ?
C004 C00E H00K 109.5 . . ?
C004 C00E C00G 110.81(8) . . ?
H00J C00E H00K 108.1 . . ?
C00G C00E H00J 109.5 . . ?
C00G C00E H00K 109.5 . . ?
C009 C00F H00L 109.5 . . ?
C009 C00F H00M 109.5 . . ?
C009 C00F H00N 109.5 . . ?
H00L C00F H00M 109.5 . . ?
H00L C00F H00N 109.5 . . ?
H00M C00F H00N 109.5 . . ?
C00C C00G C00E 111.11(8) . . ?
C00C C00G H00O 109.4 . . ?
C00C C00G H00P 109.4 . . ?
C00E C00G H00O 109.4 . . ?
C00E C00G H00P 109.4 . . ?
H00O C00G H00P 108.0 . . ?
C008 C00H H00Q 109.5 . . ?
C008 C00H H00R 109.5 . . ?
C008 C00H H00S 109.5 . . ?
H00Q C00H H00R 109.5 . . ?
H00Q C00H H00S 109.5 . . ?
H00R C00H H00S 109.5 . . ?

_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 1.212
_oxdiff_exptl_absorpt_empirical_full_min 0.782
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane-ethyl acetate'
####################################################################### 
# 
# 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_exp_329_auto
_database_code_depnum_ccdc_archive 'CCDC 2310477'
loop_
_audit_author_name
_audit_author_address
'Ryohei Fujita'
;Waseda University
Japan
;
_audit_update_record             
;
2023-11-25 deposited with the CCDC.	2024-02-01 downloaded from the CCDC.
;
_audit_creation_date             2023-07-20
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'halichonadin C'
_chemical_formula_moiety         'C16 H25 N'
_chemical_formula_sum            'C16 H25 N'
_chemical_formula_weight         231.37
_chemical_melting_point          406-407
_chemical_oxdiff_formula         C16H25N
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'

_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        P21/c
_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                   9.5724(2)
_cell_length_b                   19.8160(4)
_cell_length_c                   7.59510(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.166(2)
_cell_angle_gamma                90
_cell_volume                     1418.07(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5010
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.0330
_cell_measurement_theta_min      4.4710
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.856
_exptl_absorpt_coefficient_mu    0.459
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.312
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.084
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 5 0.1257
-5 6 1 0.1231
-5 6 -1 0.1207
2 0 -5 0.1473
5 -6 1 0.1180
-2 -12 0 0.0112
2 12 0 0.0655

_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.08
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
-0.3186 -1.3730 4.8635 -0.4976 0.0163 0.8673
-5.4599 5.9830 1.3020 0.8107 -0.0171 0.5853
-5.0960 6.2836 -0.7287 0.9779 -0.0229 0.2080
1.5044 -0.0074 -4.9209 0.2959 -0.0118 -0.9552
4.7292 -6.1181 1.4738 -0.9982 0.0242 -0.0542
-1.9229 -12.2274 0.1809 -0.1839 0.9829 -0.0092
2.0070 12.1710 -0.3130 0.1840 -0.9827 -0.0194

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            9021
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.070
_diffrn_reflns_theta_min         4.463
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00 -22.00   0.50    0.21    --  -96.00  45.00 120.00   58
  2  ω    -50.00 -23.00   0.50    0.21    --  -96.00  45.00   0.00   54
  3  ω    -63.00 -30.00   0.50    0.21    --  -96.00  61.00 -30.00   66
  4  ω    -50.00 -21.00   0.50    0.21    --  -96.00  45.00 -60.00   58
  5  ω    -49.00 -22.00   0.50    0.21    --  -96.00  45.00 -90.00   54
  6  ω    -49.00 -24.00   0.50    0.21    --  -96.00  45.00-180.00   50
  7  ω    -47.00 -21.00   0.50    0.21    --  -96.00  45.00  30.00   52
  8  ω    -49.00 -23.00   0.50    0.21    --  -96.00  45.00  90.00   52
  9  ω    -70.00 -45.00   0.50    0.05    --  -42.99 117.00 160.00   50
 10  ω    -69.00 -32.00   0.50    0.21    --  -96.00 164.00 -50.00   74
 11  ω    -97.00 -72.00   0.50    0.05    --  -42.99 164.00 -50.00   50
 12  ω   -148.00-122.00   0.50    0.21    --  -96.00-117.00  73.00   52
 13  ω   -114.00 -83.00   0.50    0.05    --  -42.99-164.00 -75.00   62
 14  ω    -77.00 -48.00   0.50    0.05    --  -42.99-164.00 -75.00   58
 15  ω   -116.00 -22.00   0.50    0.05    --  -42.99 -57.00 -30.00  188
 16  ω    127.00 178.00   0.50    0.21    --  108.01  30.00 -30.00  102
 17  ω     88.00 113.00   0.50    0.21    --  108.01 164.00 -50.00   50
 18  ω     84.00 114.00   0.50    0.21    --  108.01  30.00 -30.00   60
 19  ω     38.00  68.00   0.50    0.21    --  108.01 -61.00-150.00   60
 20  ω     45.00  70.00   0.50    0.21    --  108.01 -61.00-120.00   50
 21  ω    -33.00  32.00   0.50    0.05    --   42.99 -19.00 120.00  130
 22  ω     71.00  99.00   0.50    0.21    --  108.01 -77.00  90.00   56
 23  ω     42.00  68.00   0.50    0.21    --  108.01 -77.00  90.00   52
 24  ω     34.00  60.00   0.50    0.21    --  108.01 -61.00  90.00   52
 25  ω     50.00  76.00   0.50    0.21    --  108.01 -95.00  90.00   52
 26  ω     37.00 106.00   0.50    0.21    --  108.01-117.00  73.00  138
 27  ω     59.00  84.00   0.50    0.05    --   42.99-117.00  73.00   50
 28  ω     81.00 106.00   0.50    0.21    --  108.01 -95.00  90.00   50
 29  ω     63.00 109.00   0.50    0.05    --   42.99-164.00 -75.00   92
 30  ω     96.00 133.00   0.50    0.21    --  108.01-164.00 -75.00   74
 31  ω     54.00  87.00   0.50    0.21    --  108.01-164.00 -75.00   66
;
_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      -0.1346032000
_diffrn_orient_matrix_UB_12      0.0347068000
_diffrn_orient_matrix_UB_13      -0.1013232000
_diffrn_orient_matrix_UB_21      -0.0770484000
_diffrn_orient_matrix_UB_22      -0.0685802000
_diffrn_orient_matrix_UB_23      -0.0210609000
_diffrn_orient_matrix_UB_31      -0.0520283000
_diffrn_orient_matrix_UB_32      0.0115686000
_diffrn_orient_matrix_UB_33      0.1781803000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2441
_reflns_number_total             2768
_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 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2768
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.064
_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)+(0.0514P)²+0.3504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1179
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C002(H002), C003(H003), C004(H004), C007(H007)
2.b Secondary CH2 refined with riding coordinates:
 C008(H00A,H00B), C00B(H00I,H00J), C00D(H00M,H00N), C00E(H00O,H00P), C00F(H00Q,
 H00R)
2.c X=CH2 refined with riding coordinates:
 C00C(H00K,H00L)
2.d Idealised Me refined as rotating group:
 C009(H00C,H00D,H00E), C00A(H00F,H00G,H00H), C00G(H00S,H00T,H00U)
;
_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
N001 N 0.48142(11) 0.61354(6) 0.51018(13) 0.0319(3) Uani 1 1 d . . . . .
C002 C 0.39912(11) 0.61256(6) 0.65245(14) 0.0207(2) Uani 1 1 d . . . . .
H002 H 0.398909 0.565654 0.700965 0.025 Uiso 1 1 calc R U . . .
C003 C 0.46920(12) 0.66020(6) 0.80299(14) 0.0233(3) Uani 1 1 d . . . . .
H003 H 0.464346 0.706680 0.750973 0.028 Uiso 1 1 calc R U . . .
C004 C 0.24589(12) 0.63340(5) 0.57647(14) 0.0216(3) Uani 1 1 d . . . . .
H004 H 0.251029 0.680870 0.533356 0.026 Uiso 1 1 calc R U . . .
C005 C 0.15237(12) 0.63566(6) 0.72457(15) 0.0252(3) Uani 1 1 d . . . . .
C006 C 0.17098(12) 0.59320(6) 0.41759(14) 0.0246(3) Uani 1 1 d . . . . .
C007 C 0.62737(12) 0.64478(6) 0.86972(15) 0.0262(3) Uani 1 1 d . . . . .
H007 H 0.674939 0.644748 0.762603 0.031 Uiso 1 1 calc R U . . .
C008 C 0.37884(13) 0.66094(7) 0.95016(16) 0.0294(3) Uani 1 1 d . . . . .
H00A H 0.379449 0.615470 1.004321 0.035 Uiso 1 1 calc R U . . .
H00B H 0.420322 0.693002 1.045078 0.035 Uiso 1 1 calc R U . . .
C009 C 0.13039(14) 0.56514(7) 0.79684(17) 0.0312(3) Uani 1 1 d . . . . .
H00C H 0.090349 0.535402 0.697602 0.047 Uiso 1 1 calc R U . . .
H00D H 0.064982 0.567800 0.882384 0.047 Uiso 1 1 calc R U . . .
H00E H 0.221738 0.547043 0.856858 0.047 Uiso 1 1 calc R U . . .
C00A C 0.65433(13) 0.57602(6) 0.95875(16) 0.0304(3) Uani 1 1 d . . . . .
H00F H 0.614519 0.575206 1.069080 0.046 Uiso 1 1 calc R U . . .
H00G H 0.756747 0.567680 0.987228 0.046 Uiso 1 1 calc R U . . .
H00H H 0.609062 0.540907 0.877227 0.046 Uiso 1 1 calc R U . . .
C00B C 0.03032(13) 0.62367(6) 0.33514(17) 0.0310(3) Uani 1 1 d . . . . .
H00I H -0.015874 0.594928 0.234972 0.037 Uiso 1 1 calc R U . . .
H00J H 0.046043 0.668849 0.286506 0.037 Uiso 1 1 calc R U . . .
C00C C 0.21648(13) 0.53551(7) 0.36081(16) 0.0322(3) Uani 1 1 d . . . . .
H00K H 0.159936 0.511863 0.265049 0.039 Uiso 1 1 calc R U . . .
H00L H 0.305717 0.517704 0.415787 0.039 Uiso 1 1 calc R U . . .
C00D C -0.06662(13) 0.63001(7) 0.47374(18) 0.0330(3) Uani 1 1 d . . . . .
H00M H -0.095271 0.584471 0.507475 0.040 Uiso 1 1 calc R U . . .
H00N H -0.153509 0.655066 0.421250 0.040 Uiso 1 1 calc R U . . .
C00E C 0.22603(14) 0.68157(7) 0.87575(18) 0.0349(3) Uani 1 1 d . . . . .
H00O H 0.225814 0.728415 0.830377 0.042 Uiso 1 1 calc R U . . .
H00P H 0.170696 0.681071 0.974238 0.042 Uiso 1 1 calc R U . . .
C00F C 0.00863(14) 0.66692(7) 0.64049(19) 0.0347(3) Uani 1 1 d . . . . .
H00Q H -0.054231 0.667096 0.730945 0.042 Uiso 1 1 calc R U . . .
H00R H 0.024237 0.714425 0.608550 0.042 Uiso 1 1 calc R U . . .
C00G C 0.69773(14) 0.70011(7) 0.99545(18) 0.0361(3) Uani 1 1 d . . . . .
H00S H 0.675566 0.744330 0.939724 0.054 Uiso 1 1 calc R U . . .
H00T H 0.800782 0.693397 1.018651 0.054 Uiso 1 1 calc R U . . .
H00U H 0.661927 0.698033 1.108503 0.054 Uiso 1 1 calc R U . . .
C00H C 0.54728(16) 0.61547(11) 0.39700(19) 0.0574(5) Uani 1 1 d . . . . .


_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
N001 C002 1.4454(14) . ?
N001 C00H 1.1529(18) . ?
C002 C003 1.5420(15) . ?
C002 C004 1.5349(15) . ?
C003 C007 1.5401(16) . ?
C003 C008 1.5294(16) . ?
C004 C005 1.5570(15) . ?
C004 C006 1.5164(15) . ?
C005 C009 1.5294(17) . ?
C005 C00E 1.5354(17) . ?
C005 C00F 1.5409(17) . ?
C006 C00B 1.5073(17) . ?
C006 C00C 1.3225(18) . ?
C007 C00A 1.5229(17) . ?
C007 C00G 1.5298(17) . ?
C008 C00E 1.5279(18) . ?
C00B C00D 1.5264(18) . ?
C00D C00F 1.5283(18) . ?

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
C00H N001 C002 178.87(16) . . ?
N001 C002 C003 108.84(9) . . ?
N001 C002 C004 109.03(9) . . ?
C004 C002 C003 112.08(9) . . ?
C007 C003 C002 113.35(9) . . ?
C008 C003 C002 108.64(9) . . ?
C008 C003 C007 114.29(9) . . ?
C002 C004 C005 111.67(9) . . ?
C006 C004 C002 116.36(9) . . ?
C006 C004 C005 109.79(9) . . ?
C009 C005 C004 111.48(9) . . ?
C009 C005 C00E 110.31(10) . . ?
C009 C005 C00F 110.28(10) . . ?
C00E C005 C004 108.09(10) . . ?
C00E C005 C00F 109.29(10) . . ?
C00F C005 C004 107.30(10) . . ?
C00B C006 C004 112.48(10) . . ?
C00C C006 C004 125.24(11) . . ?
C00C C006 C00B 122.16(11) . . ?
C00A C007 C003 113.79(10) . . ?
C00A C007 C00G 110.04(10) . . ?
C00G C007 C003 111.24(10) . . ?
C00E C008 C003 111.11(10) . . ?
C006 C00B C00D 110.71(10) . . ?
C00B C00D C00F 110.85(10) . . ?
C008 C00E C005 113.66(10) . . ?
C00D C00F C005 114.01(10) . . ?

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
N001 C002 C003 C007 -53.80(12) . . . . ?
N001 C002 C003 C008 178.00(9) . . . . ?
N001 C002 C004 C005 -178.14(9) . . . . ?
N001 C002 C004 C006 54.74(12) . . . . ?
C002 C003 C007 C00A -64.55(12) . . . . ?
C002 C003 C007 C00G 170.49(9) . . . . ?
C002 C003 C008 C00E -56.47(13) . . . . ?
C002 C004 C005 C009 -67.35(12) . . . . ?
C002 C004 C005 C00E 54.05(12) . . . . ?
C002 C004 C005 C00F 171.81(9) . . . . ?
C002 C004 C006 C00B -171.31(9) . . . . ?
C002 C004 C006 C00C 12.65(16) . . . . ?
C003 C002 C004 C005 -57.59(11) . . . . ?
C003 C002 C004 C006 175.30(9) . . . . ?
C003 C008 C00E C005 58.03(15) . . . . ?
C004 C002 C003 C007 -174.47(9) . . . . ?
C004 C002 C003 C008 57.33(12) . . . . ?
C004 C005 C00E C008 -54.94(14) . . . . ?
C004 C005 C00F C00D 56.10(14) . . . . ?
C004 C006 C00B C00D -57.25(13) . . . . ?
C005 C004 C006 C00B 60.65(12) . . . . ?
C005 C004 C006 C00C -115.39(13) . . . . ?
C006 C004 C005 C009 63.25(12) . . . . ?
C006 C004 C005 C00E -175.35(10) . . . . ?
C006 C004 C005 C00F -57.59(12) . . . . ?
C006 C00B C00D C00F 52.33(14) . . . . ?
C007 C003 C008 C00E 175.87(10) . . . . ?
C008 C003 C007 C00A 60.67(13) . . . . ?
C008 C003 C007 C00G -64.29(13) . . . . ?
C009 C005 C00E C008 67.17(14) . . . . ?
C009 C005 C00F C00D -65.49(14) . . . . ?
C00B C00D C00F C005 -54.22(15) . . . . ?
C00C C006 C00B C00D 118.93(13) . . . . ?
C00E C005 C00F C00D 173.08(11) . . . . ?
C00F C005 C00E C008 -171.42(11) . . . . ?

_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 1.298
_oxdiff_exptl_absorpt_empirical_full_min 0.738

# start Validation Reply Form
_vrf_PLAT315_exp_329_auto        
;
PROBLEM: Singly Bonded Carbon Detected (H-atoms Missing). C00H Check
RESPONSE: NMR measurements confirmed that the hydrogen atom did not exist there.
;
# end Validation Reply Form
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane-dichloromethane'
####################################################################### 
# 
# 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_exp_197_auto
_database_code_depnum_ccdc_archive 'CCDC 2310476'
loop_
_audit_author_name
_audit_author_address
'Ryohei Fujita'
;Waseda University
Japan
;
_audit_update_record             
;
2023-11-25 deposited with the CCDC.	2024-02-01 downloaded from the CCDC.
;
_audit_creation_date             2023-07-26
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        'methyldecalin 197'
_chemical_formula_moiety         'C16 H27 N O'
_chemical_formula_sum            'C16 H27 N O'
_chemical_formula_weight         249.38
_chemical_melting_point          406-407
_chemical_oxdiff_formula         'C16 H27 N O'
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'

_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        P21/n
_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                   5.89130(10)
_cell_length_b                   26.1001(4)
_cell_length_c                   9.5853(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.765(2)
_cell_angle_gamma                90
_cell_volume                     1452.52(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9453
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.7190
_cell_measurement_theta_min      3.4270
_shelx_estimated_absorpt_T_max   0.924
_shelx_estimated_absorpt_T_min   0.874
_exptl_absorpt_coefficient_mu    0.532
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.561
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -16 2 0.1251
-4 -2 0 0.0661
0 16 -2 0.1074
4 1 0 0.0789
2 -14 -1 0.1290
1 -9 -5 0.1170
0 1 -6 0.0879
1 -2 -6 0.1135
0 5 -6 0.1025
-2 13 0 0.1094
0 -5 6 0.0596
0 -13 4 0.1039
3 -10 0 0.1108
4 -5 -2 0.1063
3 2 -4 0.1101
0 13 -4 0.1094
-1 13 -3 0.1100
-3 -6 5 0.0886
0 -17 1 0.1376
3 0 3 0.0783
0 17 0 0.0982
-2 11 -2 0.1111
-3 -2 -3 0.0861
2 -15 -2 0.1380
1 -5 5 0.0757
0 7 6 0.0674
-2 15 1 0.1030
-1 1 -6 0.0872

_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.149
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
-0.0138 -15.7749 2.2374 0.5212 0.1016 0.8473
-3.7572 -1.8382 0.0951 0.8579 0.1582 -0.4888
0.0089 15.7735 -2.2374 -0.5202 -0.1014 -0.8480
3.7611 1.0992 0.0099 -0.8345 -0.1536 0.5292
2.0833 -14.0869 -1.2374 -0.0962 0.4917 0.8655
1.1204 -8.7212 -5.2478 -0.1806 0.9598 0.2147
-0.3789 1.0092 -5.9866 -0.1573 0.8533 -0.4972
1.0255 -2.0143 -6.1446 -0.3788 0.9120 -0.1574
-0.1961 4.8149 -5.8172 -0.2965 0.7201 -0.6274
-2.3451 13.3414 0.2631 0.1387 -0.3217 -0.9366
0.3156 -5.4289 5.7001 0.2839 -0.6904 0.6654
0.2387 -12.9839 3.8547 0.4462 -0.2164 0.8684
2.9791 -10.2855 0.1482 -0.3451 0.1590 0.9250
3.5844 -4.9215 -2.1774 -0.7056 0.3318 0.6261
3.2811 1.8067 -3.9878 -0.8919 0.4227 0.1609
-0.0573 12.8201 -3.9919 -0.4853 0.2349 -0.8422
-1.0066 13.3079 -3.1574 -0.2666 0.1316 -0.9548
-2.7027 -5.5947 4.5826 0.8947 -0.4256 0.1357
0.4707 -16.6405 0.7292 0.3888 0.3279 0.8610
3.1156 0.4065 2.6966 -0.5828 -0.5035 0.6378
0.0314 16.9169 -0.2987 -0.4888 -0.4141 -0.7678
-2.2620 11.2563 -2.1804 0.0933 0.0862 -0.9919
-3.1018 -2.1067 -2.6518 0.6288 0.5424 -0.5571
1.6254 -15.0371 -1.5309 0.0179 0.5748 0.8181
1.4768 -4.5890 5.0010 -0.0123 -0.6495 0.7603
0.0628 7.3247 5.5095 -0.0242 -0.9986 0.0463
-1.7366 15.0433 0.9150 -0.0159 -0.4820 -0.8760
-1.1012 0.8196 -5.5617 0.0174 0.8203 -0.5717

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16600
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.180
_diffrn_reflns_theta_min         3.387
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_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 0.942
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    153.00 178.00   0.50    0.08    --  108.01 125.00 150.00   50
  2  ω     95.00 125.00   0.50    0.08    --  108.01 125.00 150.00   60
  3  ω     86.00 140.00   0.50    0.08    --  108.01  55.00 -63.00  108
  4  ω     41.00  67.00   0.50    0.05    --   42.99  55.00 -63.00   52
  5  ω     68.00  94.00   0.50    0.05    --   42.99  55.00 -63.00   52
  6  ω     70.00 100.00   0.50    0.08    --  108.01 -77.00 150.00   60
  7  ω     36.00  62.00   0.50    0.08    --  108.01 -55.00 152.00   52
  8  ω     36.00  65.00   0.50    0.08    --  108.01 -61.00  60.00   58
  9  ω     39.00  71.00   0.50    0.08    --  108.01 -61.00   0.00   64
 10  ω     48.00 105.00   0.50    0.08    --  108.01 -95.00 -90.00  114
 11  ω     77.00 112.00   0.50    0.08    --  108.01-125.00 -60.00   70
 12  ω     41.00  67.00   0.50    0.08    --  108.01-125.00 -60.00   52
 13  ω     34.00  94.00   0.50    0.05    --   42.99-125.00   0.00  120
 14  ω    -31.00  -2.00   0.50    0.05    --   42.99 -38.00-120.00   58
 15  ω      8.00  42.00   0.50    0.05    --   42.99 -38.00-120.00   68
 16  ω   -115.00 -26.00   0.50    0.05    --  -42.99 -57.00  90.00  178
 17  ω   -114.00 -22.00   0.50    0.05    --  -42.99 -55.00 152.00  184
 18  ω      0.00  26.00   0.50    0.05    --   42.99 -55.00 152.00   52
 19  ω   -119.00 -23.00   0.50    0.05    --  -42.99 -38.00   0.00  192
 20  ω   -119.00 -70.00   0.50    0.05    --  -42.99 -38.00 -30.00   98
 21  ω   -102.00 -67.00   0.50    0.08    --  -96.00 -77.00  60.00   70
 22  ω    -97.00 -72.00   0.50    0.08    --  -96.00 -61.00  60.00   50
 23  ω   -164.00 -67.00   0.50    0.08    --  -96.00 -77.00  30.00  194
 24  ω   -163.00-113.00   0.50    0.08    --  -96.00 -61.00  60.00  100
 25  ω    -94.00 -69.00   0.50    0.08    --  -96.00 -77.00  90.00   50
 26  ω   -131.00 -78.00   0.50    0.08    --  -96.00 -55.00 152.00  106
 27  ω   -108.00 -78.00   0.50    0.08    --  -96.00 -45.00  90.00   60
 28  ω   -104.00 -76.00   0.50    0.08    --  -96.00 -45.00  60.00   56
 29  ω   -121.00 -75.00   0.50    0.08    --  -96.00 -45.00  30.00   92
 30  ω   -152.00-125.00   0.50    0.08    --  -96.00 -45.00  60.00   54
 31  ω   -174.00-100.00   0.50    0.08    --  -96.00 -30.00   0.00  148
 32  ω    -47.00 -20.00   0.50    0.08    --  -96.00  45.00 -30.00   54
 33  ω    -62.00 -27.00   0.50    0.08    --  -96.00  55.00 -63.00   70
 34  ω    -69.00 -22.00   0.50    0.08    --  -96.00  61.00 -30.00   94
 35  ω    -51.00 -20.00   0.50    0.08    --  -96.00  45.00-120.00   62
 36  ω    -40.00 -15.00   0.50    0.05    --  -42.99  55.00 -63.00   50
 37  ω    -46.00 -20.00   0.50    0.08    --  -96.00  45.00  60.00   52
 38  ω    -51.00 -25.00   0.50    0.08    --  -96.00  45.00  90.00   52
 39  ω    -51.00 -26.00   0.50    0.08    --  -96.00  45.00 120.00   50
 40  ω    -59.00 -22.00   0.50    0.08    --  -96.00  61.00 150.00   74
 41  ω    -48.00 -22.00   0.50    0.08    --  -96.00  45.00 150.00   52
 42  ω   -171.00 -84.00   0.50    0.08    --  -96.00 -95.00 120.00  174
 43  ω   -167.00-141.00   0.50    0.08    --  -96.00 -95.00-120.00   52
 44  ω   -130.00 -88.00   0.50    0.08    --  -96.00 -95.00-120.00   84
;
_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      -0.2138135000
_diffrn_orient_matrix_UB_12      -0.0278765000
_diffrn_orient_matrix_UB_13      0.0351019000
_diffrn_orient_matrix_UB_21      -0.0325701000
_diffrn_orient_matrix_UB_22      -0.0269809000
_diffrn_orient_matrix_UB_23      -0.1450147000
_diffrn_orient_matrix_UB_31      0.1535481000
_diffrn_orient_matrix_UB_32      -0.0445117000
_diffrn_orient_matrix_UB_33      0.0658336000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2610
_reflns_number_total             2821
_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 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2821
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.061
_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)+(0.0490P)²+0.4459P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1021
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C003(H003), C004(H004), C005(H005), C00E(H00M)
2.b Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B), C00A(H00C,H00D), C00D(H00K,H00L), C00F(H00N,H00O), C00G(H00P,
 H00Q)
2.c Idealised Me refined as rotating group:
 C00B(H00E,H00F,H00G), C00C(H00H,H00I,H00J), C00H(H00R,H00S,H00T), C00I(H00U,
 H00V,H00W)
2.d Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_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 0.62137(12) 0.71824(3) 0.59029(8) 0.02260(19) Uani 1 1 d . . . . .
H001 H 0.6067 0.7470 0.6269 0.034 Uiso 1 1 calc R U . . .
N002 N 1.04186(19) 0.68826(4) 0.24486(10) 0.0300(3) Uani 1 1 d . . . . .
C003 C 0.86921(16) 0.64751(4) 0.56210(10) 0.0152(2) Uani 1 1 d . . . . .
H003 H 1.0359 0.6379 0.5788 0.018 Uiso 1 1 calc R U . . .
C004 C 0.79769(18) 0.58400(4) 0.34730(10) 0.0173(2) Uani 1 1 d . . . . .
H004 H 0.9654 0.5755 0.3591 0.021 Uiso 1 1 calc R U . . .
C005 C 0.78347(17) 0.64056(4) 0.39985(10) 0.0164(2) Uani 1 1 d . . . . .
H005 H 0.6204 0.6526 0.3761 0.020 Uiso 1 1 calc R U . . .
C006 C 0.74873(18) 0.60814(4) 0.64791(11) 0.0178(2) Uani 1 1 d . . . . .
C007 C 0.92582(19) 0.66982(4) 0.31540(11) 0.0209(2) Uani 1 1 d . . . . .
C008 C 0.85925(17) 0.70331(4) 0.61754(11) 0.0180(2) Uani 1 1 d . . . . .
C009 C 0.79499(19) 0.55421(4) 0.59603(11) 0.0203(2) Uani 1 1 d . . . . .
H00A H 0.9633 0.5484 0.6097 0.024 Uiso 1 1 calc R U . . .
H00B H 0.7281 0.5287 0.6538 0.024 Uiso 1 1 calc R U . . .
C00A C 0.69331(18) 0.54630(4) 0.44053(11) 0.0197(2) Uani 1 1 d . . . . .
H00C H 0.5243 0.5512 0.4266 0.024 Uiso 1 1 calc R U . . .
H00D H 0.7240 0.5108 0.4124 0.024 Uiso 1 1 calc R U . . .
C00B C 0.9989(2) 0.74210(4) 0.54740(12) 0.0234(2) Uani 1 1 d . . . . .
H00E H 0.9229 0.7481 0.4497 0.035 Uiso 1 1 calc R U . . .
H00F H 1.1542 0.7286 0.5474 0.035 Uiso 1 1 calc R U . . .
H00G H 1.0093 0.7744 0.6002 0.035 Uiso 1 1 calc R U . . .
C00C C 0.48612(19) 0.61539(4) 0.63297(12) 0.0243(2) Uani 1 1 d . . . . .
H00H H 0.4535 0.6461 0.6851 0.036 Uiso 1 1 calc R U . . .
H00I H 0.4184 0.5854 0.6715 0.036 Uiso 1 1 calc R U . . .
H00J H 0.4194 0.6194 0.5327 0.036 Uiso 1 1 calc R U . . .
C00D C 0.8577(2) 0.61210(4) 0.80509(11) 0.0255(3) Uani 1 1 d . . . . .
H00K H 0.7775 0.5882 0.8605 0.031 Uiso 1 1 calc R U . . .
H00L H 1.0209 0.6014 0.8165 0.031 Uiso 1 1 calc R U . . .
C00E C 0.7013(2) 0.57799(4) 0.18733(11) 0.0223(2) Uani 1 1 d . . . . .
H00M H 0.7799 0.6042 0.1360 0.027 Uiso 1 1 calc R U . . .
C00F C 0.9559(2) 0.70419(4) 0.77718(11) 0.0239(2) Uani 1 1 d . . . . .
H00N H 1.1234 0.6973 0.7906 0.029 Uiso 1 1 calc R U . . .
H00O H 0.9351 0.7390 0.8138 0.029 Uiso 1 1 calc R U . . .
C00G C 0.8457(2) 0.66599(5) 0.86445(12) 0.0288(3) Uani 1 1 d . . . . .
H00P H 0.6828 0.6755 0.8635 0.035 Uiso 1 1 calc R U . . .
H00Q H 0.9265 0.6668 0.9638 0.035 Uiso 1 1 calc R U . . .
C00H C 0.7619(2) 0.52534(4) 0.13378(12) 0.0279(3) Uani 1 1 d . . . . .
H00R H 0.9278 0.5194 0.1607 0.042 Uiso 1 1 calc R U . . .
H00S H 0.7195 0.5242 0.0305 0.042 Uiso 1 1 calc R U . . .
H00T H 0.6773 0.4988 0.1759 0.042 Uiso 1 1 calc R U . . .
C00I C 0.4422(2) 0.58772(5) 0.14888(13) 0.0344(3) Uani 1 1 d . . . . .
H00U H 0.3586 0.5613 0.1922 0.052 Uiso 1 1 calc R U . . .
H00V H 0.3959 0.5866 0.0458 0.052 Uiso 1 1 calc R U . . .
H00W H 0.4059 0.6215 0.1840 0.052 Uiso 1 1 calc R U . . .


_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 H001 0.8400 . ?
O001 C008 1.4352(12) . ?
N002 C007 1.1458(15) . ?
C003 H003 1.0000 . ?
C003 C005 1.5621(13) . ?
C003 C006 1.5602(13) . ?
C003 C008 1.5547(13) . ?
C004 H004 1.0000 . ?
C004 C005 1.5666(13) . ?
C004 C00A 1.5268(14) . ?
C004 C00E 1.5502(14) . ?
C005 H005 1.0000 . ?
C005 C007 1.4738(14) . ?
C006 C009 1.5326(14) . ?
C006 C00C 1.5410(15) . ?
C006 C00D 1.5376(14) . ?
C008 C00B 1.5304(15) . ?
C008 C00F 1.5397(14) . ?
C009 H00A 0.9900 . ?
C009 H00B 0.9900 . ?
C009 C00A 1.5232(14) . ?
C00A H00C 0.9900 . ?
C00A H00D 0.9900 . ?
C00B H00E 0.9800 . ?
C00B H00F 0.9800 . ?
C00B H00G 0.9800 . ?
C00C H00H 0.9800 . ?
C00C H00I 0.9800 . ?
C00C H00J 0.9800 . ?
C00D H00K 0.9900 . ?
C00D H00L 0.9900 . ?
C00D C00G 1.5234(16) . ?
C00E H00M 1.0000 . ?
C00E C00H 1.5302(15) . ?
C00E C00I 1.5298(17) . ?
C00F H00N 0.9900 . ?
C00F H00O 0.9900 . ?
C00F C00G 1.5163(16) . ?
C00G H00P 0.9900 . ?
C00G H00Q 0.9900 . ?
C00H H00R 0.9800 . ?
C00H H00S 0.9800 . ?
C00H H00T 0.9800 . ?
C00I H00U 0.9800 . ?
C00I H00V 0.9800 . ?
C00I H00W 0.9800 . ?

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
C008 O001 H001 109.5 . . ?
C005 C003 H003 105.8 . . ?
C006 C003 H003 105.8 . . ?
C006 C003 C005 110.44(8) . . ?
C008 C003 H003 105.8 . . ?
C008 C003 C005 115.12(8) . . ?
C008 C003 C006 112.94(8) . . ?
C005 C004 H004 106.2 . . ?
C00A C004 H004 106.2 . . ?
C00A C004 C005 111.73(8) . . ?
C00A C004 C00E 113.42(8) . . ?
C00E C004 H004 106.2 . . ?
C00E C004 C005 112.51(8) . . ?
C003 C005 C004 113.81(8) . . ?
C003 C005 H005 109.0 . . ?
C004 C005 H005 109.0 . . ?
C007 C005 C003 111.63(8) . . ?
C007 C005 C004 104.20(8) . . ?
C007 C005 H005 109.0 . . ?
C009 C006 C003 108.18(8) . . ?
C009 C006 C00C 108.28(8) . . ?
C009 C006 C00D 108.17(8) . . ?
C00C C006 C003 114.17(8) . . ?
C00D C006 C003 108.71(8) . . ?
C00D C006 C00C 109.17(9) . . ?
N002 C007 C005 173.60(11) . . ?
O001 C008 C003 106.52(8) . . ?
O001 C008 C00B 108.77(8) . . ?
O001 C008 C00F 111.21(8) . . ?
C00B C008 C003 114.54(8) . . ?
C00B C008 C00F 106.92(8) . . ?
C00F C008 C003 108.95(8) . . ?
C006 C009 H00A 109.1 . . ?
C006 C009 H00B 109.1 . . ?
H00A C009 H00B 107.9 . . ?
C00A C009 C006 112.33(8) . . ?
C00A C009 H00A 109.1 . . ?
C00A C009 H00B 109.1 . . ?
C004 C00A H00C 109.5 . . ?
C004 C00A H00D 109.5 . . ?
C009 C00A C004 110.78(8) . . ?
C009 C00A H00C 109.5 . . ?
C009 C00A H00D 109.5 . . ?
H00C C00A H00D 108.1 . . ?
C008 C00B H00E 109.5 . . ?
C008 C00B H00F 109.5 . . ?
C008 C00B H00G 109.5 . . ?
H00E C00B H00F 109.5 . . ?
H00E C00B H00G 109.5 . . ?
H00F C00B H00G 109.5 . . ?
C006 C00C H00H 109.5 . . ?
C006 C00C H00I 109.5 . . ?
C006 C00C H00J 109.5 . . ?
H00H C00C H00I 109.5 . . ?
H00H C00C H00J 109.5 . . ?
H00I C00C H00J 109.5 . . ?
C006 C00D H00K 109.0 . . ?
C006 C00D H00L 109.0 . . ?
H00K C00D H00L 107.8 . . ?
C00G C00D C006 112.94(9) . . ?
C00G C00D H00K 109.0 . . ?
C00G C00D H00L 109.0 . . ?
C004 C00E H00M 107.1 . . ?
C00H C00E C004 110.83(9) . . ?
C00H C00E H00M 107.1 . . ?
C00I C00E C004 113.87(9) . . ?
C00I C00E H00M 107.1 . . ?
C00I C00E C00H 110.39(9) . . ?
C008 C00F H00N 108.6 . . ?
C008 C00F H00O 108.6 . . ?
H00N C00F H00O 107.6 . . ?
C00G C00F C008 114.70(9) . . ?
C00G C00F H00N 108.6 . . ?
C00G C00F H00O 108.6 . . ?
C00D C00G H00P 109.6 . . ?
C00D C00G H00Q 109.6 . . ?
C00F C00G C00D 110.48(9) . . ?
C00F C00G H00P 109.6 . . ?
C00F C00G H00Q 109.6 . . ?
H00P C00G H00Q 108.1 . . ?
C00E C00H H00R 109.5 . . ?
C00E C00H H00S 109.5 . . ?
C00E C00H H00T 109.5 . . ?
H00R C00H H00S 109.5 . . ?
H00R C00H H00T 109.5 . . ?
H00S C00H H00T 109.5 . . ?
C00E C00I H00U 109.5 . . ?
C00E C00I H00V 109.5 . . ?
C00E C00I H00W 109.5 . . ?
H00U C00I H00V 109.5 . . ?
H00U C00I H00W 109.5 . . ?
H00V C00I H00W 109.5 . . ?

_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 1.290
_oxdiff_exptl_absorpt_empirical_full_min 0.813
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane-ethyl acetate'
