# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_TR1_a
_database_code_depnum_ccdc_archive 'CCDC 1872189'
_audit_update_record             
;
2018-10-09 deposited with the CCDC.
2019-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H25 N'
_chemical_formula_weight         291.42

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   9.944(14)
_cell_length_b                   12.969(19)
_cell_length_c                   14.91(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.99(4)
_cell_angle_gamma                90
_cell_volume                     1920(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.008
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.058
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            76735
_diffrn_reflns_av_unetI/netI     0.1959
_diffrn_reflns_av_R_equivalents  0.3288
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.082
_diffrn_reflns_theta_max         30.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.822
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.822
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.822
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4764
_reflns_number_gt                1699
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4764
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2388
_refine_ls_R_factor_gt           0.0801
_refine_ls_wR_factor_ref         0.2873
_refine_ls_wR_factor_gt          0.1965
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_restrained_S_all      0.922
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

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 0.2958(3) 0.8482(3) 0.5300(2) 0.0596(8) Uani 1 1 d . . . . .
C1 C 0.4802(3) 0.8839(2) 0.4325(2) 0.0504(8) Uani 1 1 d . . . . .
C003 C 0.4336(3) 0.8342(2) 0.5099(2) 0.0500(8) Uani 1 1 d . . . . .
C004 C 0.1992(3) 0.6723(3) 0.5285(2) 0.0585(9) Uani 1 1 d . . . . .
C005 C 0.5242(3) 0.7758(2) 0.5660(2) 0.0560(8) Uani 1 1 d . . . . .
C006 C 0.2068(3) 0.7731(3) 0.5651(2) 0.0545(9) Uani 1 1 d . . . . .
C007 C 0.2714(3) 0.6408(3) 0.4437(2) 0.0684(10) Uani 1 1 d . . . . .
H007 H 0.3541 0.6842 0.4405 0.082 Uiso 1 1 calc R U . . .
C008 C 0.6561(3) 0.7630(3) 0.5398(3) 0.0641(10) Uani 1 1 d . . . . .
H008 H 0.7162 0.7223 0.5766 0.077 Uiso 1 1 calc R U . . .
C009 C 0.6151(3) 0.8684(3) 0.4106(2) 0.0626(9) Uani 1 1 d . . . . .
H009 H 0.6462 0.9011 0.3586 0.075 Uiso 1 1 calc R U . . .
C00A C 0.7041(3) 0.8073(3) 0.4621(3) 0.0674(10) Uani 1 1 d . . . . .
C00B C 0.3869(3) 0.9508(3) 0.3733(2) 0.0684(10) Uani 1 1 d . . . . .
H00C H 0.4366 0.9789 0.3238 0.103 Uiso 1 1 calc R U . . .
H00D H 0.3525 1.0075 0.4090 0.103 Uiso 1 1 calc R U . . .
H00E H 0.3113 0.9091 0.3490 0.103 Uiso 1 1 calc R U . . .
C00C C 0.1232(3) 0.8029(3) 0.6356(2) 0.0628(9) Uani 1 1 d . . . . .
C00D C 0.1149(3) 0.6013(3) 0.5690(3) 0.0732(11) Uani 1 1 d . . . . .
H00F H 0.1110 0.5326 0.5470 0.088 Uiso 1 1 calc R U . . .
C00E C 0.4833(4) 0.7281(3) 0.6546(3) 0.0823(12) Uani 1 1 d . . . . .
H00G H 0.4282 0.6666 0.6420 0.123 Uiso 1 1 calc R U . . .
H00H H 0.4313 0.7784 0.6875 0.123 Uiso 1 1 calc R U . . .
H45 H 0.5643 0.7087 0.6910 0.123 Uiso 1 1 calc R U . . .
C00F C 0.0371(4) 0.6278(4) 0.6400(3) 0.0828(12) Uani 1 1 d . . . . .
H00J H -0.0176 0.5774 0.6665 0.099 Uiso 1 1 calc R U . . .
C00G C 0.0395(4) 0.7280(4) 0.6722(3) 0.0795(12) Uani 1 1 d . . . . .
H00K H -0.0162 0.7464 0.7196 0.095 Uiso 1 1 calc R U . . .
C00H C 0.1216(4) 0.9123(3) 0.6734(3) 0.0845(12) Uani 1 1 d . . . . .
H00L H 0.1851 0.9544 0.6386 0.101 Uiso 1 1 calc R U . . .
C00I C 0.1802(5) 0.6635(4) 0.3605(3) 0.1081(16) Uani 1 1 d . . . . .
H00M H 0.1002 0.6193 0.3606 0.162 Uiso 1 1 calc R U . . .
H00N H 0.2292 0.6496 0.3064 0.162 Uiso 1 1 calc R U . . .
H00O H 0.1527 0.7360 0.3610 0.162 Uiso 1 1 calc R U . . .
C00J C 0.8486(3) 0.7879(4) 0.4344(3) 0.0998(14) Uani 1 1 d . . . . .
H00P H 0.9098 0.8370 0.4653 0.150 Uiso 1 1 calc R U . . .
H00Q H 0.8525 0.7968 0.3693 0.150 Uiso 1 1 calc R U . . .
H00R H 0.8756 0.7174 0.4508 0.150 Uiso 1 1 calc R U . . .
C00K C 0.3145(5) 0.5277(4) 0.4427(3) 0.1201(17) Uani 1 1 d . . . . .
H00S H 0.3700 0.5124 0.4973 0.180 Uiso 1 1 calc R U . . .
H42 H 0.3667 0.5147 0.3899 0.180 Uiso 1 1 calc R U . . .
H00U H 0.2344 0.4836 0.4403 0.180 Uiso 1 1 calc R U . . .
C00L C -0.0184(5) 0.9626(4) 0.6611(4) 0.1314(19) Uani 1 1 d . . . . .
H00V H -0.0832 0.9233 0.6948 0.197 Uiso 1 1 calc R U . . .
H00W H -0.0472 0.9628 0.5972 0.197 Uiso 1 1 calc R U . . .
H43 H -0.0140 1.0336 0.6834 0.197 Uiso 1 1 calc R U . . .
C00M C 0.1705(6) 0.9179(5) 0.7724(4) 0.170(3) Uani 1 1 d . . . . .
H44 H 0.1093 0.8784 0.8087 0.256 Uiso 1 1 calc R U . . .
H46 H 0.1720 0.9900 0.7921 0.256 Uiso 1 1 calc R U . . .
H41 H 0.2614 0.8889 0.7797 0.256 Uiso 1 1 calc R U . . .
H47 H 0.262(3) 0.903(3) 0.518(2) 0.065(12) Uiso 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 C003 1.430(4) . ?
N001 C006 1.433(4) . ?
N001 H47 0.81(3) . ?
C1 C003 1.419(4) . ?
C1 C009 1.411(4) . ?
C1 C00B 1.519(5) . ?
C003 C005 1.416(4) . ?
C004 C00D 1.403(5) . ?
C004 C006 1.417(5) . ?
C004 C007 1.541(5) . ?
C005 C008 1.398(5) . ?
C005 C00E 1.534(5) . ?
C006 C00C 1.427(5) . ?
C007 C00I 1.527(6) . ?
C007 C00K 1.528(6) . ?
C007 H007 1.0000 . ?
C008 C00A 1.399(5) . ?
C008 H008 0.9500 . ?
C009 C00A 1.389(5) . ?
C009 H009 0.9500 . ?
C00A C00J 1.536(5) . ?
C00B H00C 0.9800 . ?
C00B H00D 0.9800 . ?
C00B H00E 0.9800 . ?
C00C C00G 1.409(5) . ?
C00C C00H 1.527(5) . ?
C00D C00F 1.387(5) . ?
C00D H00F 0.9500 . ?
C00E H00G 0.9800 . ?
C00E H00H 0.9800 . ?
C00E H45 0.9800 . ?
C00F C00G 1.385(6) . ?
C00F H00J 0.9500 . ?
C00G H00K 0.9500 . ?
C00H C00M 1.531(7) . ?
C00H C00L 1.540(6) . ?
C00H H00L 1.0000 . ?
C00I H00M 0.9800 . ?
C00I H00N 0.9800 . ?
C00I H00O 0.9800 . ?
C00J H00P 0.9800 . ?
C00J H00Q 0.9800 . ?
C00J H00R 0.9800 . ?
C00K H00S 0.9800 . ?
C00K H42 0.9800 . ?
C00K H00U 0.9800 . ?
C00L H00V 0.9800 . ?
C00L H00W 0.9800 . ?
C00L H43 0.9800 . ?
C00M H44 0.9800 . ?
C00M H46 0.9800 . ?
C00M H41 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
C003 N001 C006 127.4(3) . . ?
C003 N001 H47 117(2) . . ?
C006 N001 H47 115(2) . . ?
C003 C1 C009 118.6(3) . . ?
C003 C1 C00B 121.0(3) . . ?
C009 C1 C00B 120.4(3) . . ?
C1 C003 C005 119.9(3) . . ?
C1 C003 N001 118.1(3) . . ?
C005 C003 N001 122.0(3) . . ?
C00D C004 C006 117.4(3) . . ?
C00D C004 C007 119.6(3) . . ?
C006 C004 C007 122.9(3) . . ?
C008 C005 C003 118.4(3) . . ?
C008 C005 C00E 119.2(3) . . ?
C003 C005 C00E 122.4(3) . . ?
C004 C006 C00C 120.8(3) . . ?
C004 C006 N001 120.5(3) . . ?
C00C C006 N001 118.6(3) . . ?
C00I C007 C00K 109.4(3) . . ?
C00I C007 C004 109.5(3) . . ?
C00K C007 C004 113.9(3) . . ?
C00I C007 H007 108.0 . . ?
C00K C007 H007 108.0 . . ?
C004 C007 H007 108.0 . . ?
C005 C008 C00A 123.3(3) . . ?
C005 C008 H008 118.4 . . ?
C00A C008 H008 118.4 . . ?
C00A C009 C1 122.7(3) . . ?
C00A C009 H009 118.7 . . ?
C1 C009 H009 118.7 . . ?
C009 C00A C008 117.1(3) . . ?
C009 C00A C00J 121.5(4) . . ?
C008 C00A C00J 121.3(4) . . ?
C1 C00B H00C 109.5 . . ?
C1 C00B H00D 109.5 . . ?
H00C C00B H00D 109.5 . . ?
C1 C00B H00E 109.5 . . ?
H00C C00B H00E 109.5 . . ?
H00D C00B H00E 109.5 . . ?
C00G C00C C006 118.5(3) . . ?
C00G C00C C00H 118.7(3) . . ?
C006 C00C C00H 122.8(3) . . ?
C00F C00D C004 122.4(4) . . ?
C00F C00D H00F 118.8 . . ?
C004 C00D H00F 118.8 . . ?
C005 C00E H00G 109.5 . . ?
C005 C00E H00H 109.5 . . ?
H00G C00E H00H 109.5 . . ?
C005 C00E H45 109.5 . . ?
H00G C00E H45 109.5 . . ?
H00H C00E H45 109.5 . . ?
C00D C00F C00G 119.8(3) . . ?
C00D C00F H00J 120.1 . . ?
C00G C00F H00J 120.1 . . ?
C00F C00G C00C 120.9(4) . . ?
C00F C00G H00K 119.6 . . ?
C00C C00G H00K 119.6 . . ?
C00M C00H C00C 113.0(4) . . ?
C00M C00H C00L 109.5(4) . . ?
C00C C00H C00L 112.1(3) . . ?
C00M C00H H00L 107.3 . . ?
C00C C00H H00L 107.3 . . ?
C00L C00H H00L 107.3 . . ?
C007 C00I H00M 109.5 . . ?
C007 C00I H00N 109.5 . . ?
H00M C00I H00N 109.5 . . ?
C007 C00I H00O 109.5 . . ?
H00M C00I H00O 109.5 . . ?
H00N C00I H00O 109.5 . . ?
C00A C00J H00P 109.5 . . ?
C00A C00J H00Q 109.5 . . ?
H00P C00J H00Q 109.5 . . ?
C00A C00J H00R 109.5 . . ?
H00P C00J H00R 109.5 . . ?
H00Q C00J H00R 109.5 . . ?
C007 C00K H00S 109.5 . . ?
C007 C00K H42 109.5 . . ?
H00S C00K H42 109.5 . . ?
C007 C00K H00U 109.5 . . ?
H00S C00K H00U 109.5 . . ?
H42 C00K H00U 109.5 . . ?
C00H C00L H00V 109.5 . . ?
C00H C00L H00W 109.5 . . ?
H00V C00L H00W 109.5 . . ?
C00H C00L H43 109.5 . . ?
H00V C00L H43 109.5 . . ?
H00W C00L H43 109.5 . . ?
C00H C00M H44 109.5 . . ?
C00H C00M H46 109.5 . . ?
H44 C00M H46 109.5 . . ?
C00H C00M H41 109.5 . . ?
H44 C00M H41 109.5 . . ?
H46 C00M H41 109.5 . . ?

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.060

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_NVK42
_database_code_depnum_ccdc_archive 'CCDC 1872190'
_audit_update_record             
;
2018-10-09 deposited with the CCDC.
2019-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C68 H84 N4'
_chemical_formula_weight         957.39

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   13.119(3)
_cell_length_b                   8.223(2)
_cell_length_c                   13.364(3)
_cell_angle_alpha                90.00(3)
_cell_angle_beta                 103.93(3)
_cell_angle_gamma                90.00(3)
_cell_volume                     1399.2(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5146
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      25.76

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.136
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   0.6820
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.065
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17734
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.953
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2525
_reflns_number_gt                2020
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0739P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2525
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1669
_refine_ls_wR_factor_gt          0.1568
_refine_ls_goodness_of_fit_ref   1.604
_refine_ls_restrained_S_all      1.604
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1 N 0.63196(11) 0.37021(17) 0.25577(10) 0.0313(4) Uani 1 1 d . . . . .
H1 H 0.6518 0.3734 0.1990 0.038 Uiso 1 1 calc R U . . .
C1 C 0.55219(13) 0.1602(2) 0.34506(12) 0.0266(4) Uani 1 1 d . . . . .
C2 C 0.68513(13) 0.4698(2) 0.33715(13) 0.0289(4) Uani 1 1 d . . . . .
C3 C 0.54736(13) 0.2642(2) 0.26095(13) 0.0269(4) Uani 1 1 d . . . . .
C4 C 0.46714(13) 0.0601(2) 0.34515(13) 0.0299(4) Uani 1 1 d . . . . .
H4 H 0.4696 -0.0066 0.4019 0.036 Uiso 1 1 calc R U . . .
C5 C 0.45922(13) 0.2622(2) 0.17723(13) 0.0308(4) Uani 1 1 d . . . . .
C6 C 0.79518(14) 0.4763(2) 0.35985(14) 0.0322(4) Uani 1 1 d . . . . .
C7 C 0.37858(13) 0.0557(2) 0.26386(13) 0.0318(4) Uani 1 1 d . . . . .
C8 C 0.37751(13) 0.1558(2) 0.18025(13) 0.0335(5) Uani 1 1 d . . . . .
H8 H 0.3199 0.1517 0.1239 0.040 Uiso 1 1 calc R U . . .
C9 C 0.62904(14) 0.5677(2) 0.39235(14) 0.0337(5) Uani 1 1 d . . . . .
C10 C 0.64896(13) 0.1485(2) 0.43176(13) 0.0342(5) Uani 1 1 d . . . . .
H10A H 0.6523 0.2407 0.4765 0.051 Uiso 1 1 calc R U . . .
H10B H 0.7101 0.1468 0.4041 0.051 Uiso 1 1 calc R U . . .
H10C H 0.6463 0.0505 0.4701 0.051 Uiso 1 1 calc R U . . .
C11 C 0.84702(15) 0.5797(2) 0.43705(14) 0.0387(5) Uani 1 1 d . . . . .
H11 H 0.9199 0.5863 0.4513 0.046 Uiso 1 1 calc R U . . .
C12 C 0.85593(15) 0.3694(2) 0.30285(15) 0.0402(5) Uani 1 1 d . . . . .
H12A H 0.9298 0.3864 0.3299 0.060 Uiso 1 1 calc R U . . .
H12B H 0.8374 0.3964 0.2309 0.060 Uiso 1 1 calc R U . . .
H12C H 0.8392 0.2574 0.3116 0.060 Uiso 1 1 calc R U . . .
C13 C 0.68575(16) 0.6660(2) 0.47122(15) 0.0412(5) Uani 1 1 d . . . . .
H13 H 0.6497 0.7281 0.5096 0.049 Uiso 1 1 calc R U . . .
C14 C 0.79368(16) 0.6737(2) 0.49383(15) 0.0449(5) Uani 1 1 d . . . . .
H14 H 0.8302 0.7408 0.5464 0.054 Uiso 1 1 calc R U . . .
C15 C 0.45244(15) 0.3747(2) 0.08719(14) 0.0422(5) Uani 1 1 d . . . . .
H15A H 0.3849 0.3635 0.0401 0.063 Uiso 1 1 calc R U . . .
H15B H 0.5064 0.3475 0.0526 0.063 Uiso 1 1 calc R U . . .
H15C H 0.4617 0.4849 0.1114 0.063 Uiso 1 1 calc R U . . .
C16 C 0.51055(15) 0.5745(2) 0.36517(17) 0.0451(5) Uani 1 1 d . . . . .
H16A H 0.4833 0.4756 0.3866 0.068 Uiso 1 1 calc R U . . .
H16B H 0.4852 0.5872 0.2920 0.068 Uiso 1 1 calc R U . . .
H16C H 0.4879 0.6651 0.3996 0.068 Uiso 1 1 calc R U . . .
C17 C 0.28789(16) -0.0525(3) 0.26675(16) 0.0512(6) Uani 1 1 d . . . . .
H17A H 0.3122 -0.1623 0.2799 0.077 Uiso 1 1 calc R U . . .
H17B H 0.2372 -0.0475 0.2017 0.077 Uiso 1 1 calc R U . . .
H17C H 0.2559 -0.0172 0.3205 0.077 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
N1 C2 1.405(2) . ?
N1 C3 1.426(2) . ?
N1 H1 0.8600 . ?
C1 C4 1.386(2) . ?
C1 C3 1.402(2) . ?
C1 C10 1.502(2) . ?
C2 C6 1.403(2) . ?
C2 C9 1.413(2) . ?
C3 C5 1.402(2) . ?
C4 C7 1.387(2) . ?
C4 H4 0.9300 . ?
C5 C8 1.392(2) . ?
C5 C15 1.503(2) . ?
C6 C11 1.383(3) . ?
C6 C12 1.510(3) . ?
C7 C8 1.385(2) . ?
C7 C17 1.493(3) . ?
C8 H8 0.9300 . ?
C9 C13 1.393(3) . ?
C9 C16 1.510(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C14 1.385(3) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.376(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C2 N1 C3 124.45(13) . . ?
C2 N1 H1 117.8 . . ?
C3 N1 H1 117.8 . . ?
C4 C1 C3 118.80(16) . . ?
C4 C1 C10 119.50(15) . . ?
C3 C1 C10 121.63(15) . . ?
C6 C2 N1 118.88(16) . . ?
C6 C2 C9 120.23(17) . . ?
N1 C2 C9 120.83(16) . . ?
C1 C3 C5 120.14(16) . . ?
C1 C3 N1 121.77(15) . . ?
C5 C3 N1 118.06(15) . . ?
C1 C4 C7 122.51(16) . . ?
C1 C4 H4 118.7 . . ?
C7 C4 H4 118.7 . . ?
C8 C5 C3 118.49(16) . . ?
C8 C5 C15 120.83(16) . . ?
C3 C5 C15 120.67(16) . . ?
C11 C6 C2 118.73(17) . . ?
C11 C6 C12 120.65(17) . . ?
C2 C6 C12 120.61(16) . . ?
C8 C7 C4 117.41(16) . . ?
C8 C7 C17 121.41(17) . . ?
C4 C7 C17 121.17(17) . . ?
C7 C8 C5 122.59(16) . . ?
C7 C8 H8 118.7 . . ?
C5 C8 H8 118.7 . . ?
C13 C9 C2 118.39(17) . . ?
C13 C9 C16 119.48(17) . . ?
C2 C9 C16 122.07(17) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C6 C11 C14 121.95(18) . . ?
C6 C11 H11 119.0 . . ?
C14 C11 H11 119.0 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C9 121.78(18) . . ?
C14 C13 H13 119.1 . . ?
C9 C13 H13 119.1 . . ?
C13 C14 C11 118.88(18) . . ?
C13 C14 H14 120.6 . . ?
C11 C14 H14 120.6 . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 C16 H16A 109.5 . . ?
C9 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C9 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7 C17 H17A 109.5 . . ?
C7 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C7 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_refine_diff_density_max         0.410
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_NVK039
_database_code_depnum_ccdc_archive 'CCDC 1872191'
_audit_update_record             
;
2018-10-09 deposited with the CCDC.
2019-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H35 N'
_chemical_formula_weight         337.53

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   12.224(4)
_cell_length_b                   9.583(3)
_cell_length_c                   18.985(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.841(10)
_cell_angle_gamma                90
_cell_volume                     2149.9(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9148
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      21.77

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.043
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   0.6103
_exptl_transmission_factor_max   0.7434
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.059
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            55792
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_av_R_equivalents  0.1170
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.398
_diffrn_reflns_theta_max         25.247
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3899
_reflns_number_gt                2362
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3899
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.1004
_refine_ls_wR_factor_gt          0.0959
_refine_ls_goodness_of_fit_ref   2.149
_refine_ls_restrained_S_all      2.149
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1 N 0.31620(12) 0.78517(14) 0.26879(8) 0.0440(4) Uani 1 1 d . . . . .
H001 H 0.3816 0.8200 0.2931 0.053 Uiso 1 1 calc R U . . .
C1 C 0.29369(14) 0.64422(18) 0.28492(10) 0.0375(5) Uani 1 1 d . . . . .
C2 C 0.26043(14) 0.54447(19) 0.22952(10) 0.0388(5) Uani 1 1 d . . . . .
C3 C 0.24521(16) 0.87457(18) 0.21826(10) 0.0365(5) Uani 1 1 d . . . . .
C4 C 0.31033(14) 0.60628(19) 0.35830(10) 0.0388(5) Uani 1 1 d . . . . .
C5 C 0.24227(15) 0.40876(19) 0.24981(11) 0.0446(5) Uani 1 1 d . . . . .
H006 H 0.2170 0.3414 0.2125 0.054 Uiso 1 1 calc R U . . .
C6 C 0.25889(15) 0.36697(19) 0.32094(11) 0.0429(5) Uani 1 1 d . . . . .
C7 C 0.29405(16) 0.95734(19) 0.17378(10) 0.0417(5) Uani 1 1 d . . . . .
C8 C 0.29362(15) 0.4677(2) 0.37457(10) 0.0458(5) Uani 1 1 d . . . . .
H009 H 0.3064 0.4410 0.4242 0.055 Uiso 1 1 calc R U . . .
C9 C 0.13026(17) 0.88831(19) 0.21509(11) 0.0439(5) Uani 1 1 d . . . . .
C10 C 0.24768(17) 0.57725(19) 0.14952(10) 0.0480(5) Uani 1 1 d . . . . .
H00B H 0.2767 0.6741 0.1465 0.058 Uiso 1 1 calc R U . . .
C11 C 0.22612(19) 1.04786(19) 0.12505(11) 0.0513(6) Uani 1 1 d . . . . .
H00C H 0.2596 1.1038 0.0949 0.062 Uiso 1 1 calc R U . . .
C12 C 0.34769(17) 0.71377(19) 0.41816(10) 0.0490(6) Uani 1 1 d . . . . .
H00D H 0.3138 0.8049 0.3980 0.059 Uiso 1 1 calc R U . . .
C13 C 0.1117(2) 1.0604(2) 0.11840(11) 0.0533(6) Uani 1 1 d . . . . .
C14 C 0.06611(17) 0.9802(2) 0.16413(12) 0.0539(6) Uani 1 1 d . . . . .
H00F H -0.0125 0.9881 0.1607 0.065 Uiso 1 1 calc R U . . .
C15 C 0.24718(18) 0.21426(19) 0.33920(12) 0.0589(6) Uani 1 1 d . . . . .
H00G H 0.1956 0.1699 0.2954 0.071 Uiso 1 1 calc R U . . .
C16 C 0.41884(16) 0.9472(2) 0.17838(11) 0.0651(6) Uani 1 1 d . . . . .
H00A H 0.4366 1.0050 0.1402 0.098 Uiso 1 1 calc R U . . .
H00E H 0.4386 0.8498 0.1717 0.098 Uiso 1 1 calc R U . . .
H00H H 0.4623 0.9801 0.2263 0.098 Uiso 1 1 calc R U . . .
C17 C 0.07598(17) 0.8127(2) 0.26749(12) 0.0680(7) Uani 1 1 d . . . . .
H00I H 0.0669 0.7138 0.2542 0.102 Uiso 1 1 calc R U . . .
H00J H 0.0017 0.8538 0.2650 0.102 Uiso 1 1 calc R U . . .
H00K H 0.1243 0.8216 0.3172 0.102 Uiso 1 1 calc R U . . .
C18 C 0.31962(19) 0.4778(2) 0.11633(11) 0.0723(7) Uani 1 1 d . . . . .
H00L H 0.3989 0.4835 0.1443 0.108 Uiso 1 1 calc R U . . .
H00M H 0.3136 0.5046 0.0657 0.108 Uiso 1 1 calc R U . . .
H00N H 0.2923 0.3820 0.1178 0.108 Uiso 1 1 calc R U . . .
C19 C 0.36116(19) 0.1418(2) 0.35209(13) 0.0765(7) Uani 1 1 d . . . . .
H00O H 0.3893 0.1501 0.3084 0.115 Uiso 1 1 calc R U . . .
H00P H 0.3526 0.0430 0.3628 0.115 Uiso 1 1 calc R U . . .
H00Q H 0.4150 0.1856 0.3934 0.115 Uiso 1 1 calc R U . . .
C20 C 0.12464(18) 0.5738(2) 0.10543(11) 0.0822(8) Uani 1 1 d . . . . .
H00R H 0.0933 0.4805 0.1085 0.123 Uiso 1 1 calc R U . . .
H10 H 0.1204 0.5959 0.0544 0.123 Uiso 1 1 calc R U . . .
H00T H 0.0810 0.6427 0.1250 0.123 Uiso 1 1 calc R U . . .
C21 C 0.47484(18) 0.7330(2) 0.43920(12) 0.0809(8) Uani 1 1 d . . . . .
H00U H 0.5110 0.6495 0.4647 0.121 Uiso 1 1 calc R U . . .
H00V H 0.4946 0.8143 0.4713 0.121 Uiso 1 1 calc R U . . .
H00W H 0.5013 0.7477 0.3952 0.121 Uiso 1 1 calc R U . . .
C22 C 0.03830(19) 1.1586(2) 0.06344(12) 0.0857(8) Uani 1 1 d . . . . .
H7 H 0.0853 1.2078 0.0366 0.129 Uiso 1 1 calc R U . . .
H9 H 0.0025 1.2267 0.0890 0.129 Uiso 1 1 calc R U . . .
H8 H -0.0203 1.1050 0.0292 0.129 Uiso 1 1 calc R U . . .
C23 C 0.1952(2) 0.1913(2) 0.40287(14) 0.0944(9) Uani 1 1 d . . . . .
H3 H 0.1787 0.0919 0.4066 0.142 Uiso 1 1 calc R U . . .
H1 H 0.1249 0.2450 0.3951 0.142 Uiso 1 1 calc R U . . .
H2 H 0.2484 0.2222 0.4480 0.142 Uiso 1 1 calc R U . . .
C24 C 0.3071(2) 0.6848(2) 0.48598(12) 0.0973(9) Uani 1 1 d . . . . .
H6 H 0.3446 0.6009 0.5102 0.146 Uiso 1 1 calc R U . . .
H4 H 0.2250 0.6703 0.4722 0.146 Uiso 1 1 calc R U . . .
H5 H 0.3255 0.7644 0.5193 0.146 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
N1 C3 1.407(2) . ?
N1 C1 1.427(2) . ?
N1 H001 0.8800 . ?
C1 C2 1.402(2) . ?
C1 C4 1.403(2) . ?
C2 C5 1.390(2) . ?
C2 C10 1.519(2) . ?
C3 C9 1.397(2) . ?
C3 C7 1.399(2) . ?
C4 C8 1.390(2) . ?
C4 C12 1.515(2) . ?
C5 C6 1.373(2) . ?
C5 H006 0.9500 . ?
C6 C8 1.389(2) . ?
C6 C15 1.519(2) . ?
C7 C11 1.380(2) . ?
C7 C16 1.509(2) . ?
C8 H009 0.9500 . ?
C9 C14 1.392(3) . ?
C9 C17 1.514(2) . ?
C10 C20 1.523(3) . ?
C10 C18 1.537(2) . ?
C10 H00B 1.0000 . ?
C11 C13 1.377(3) . ?
C11 H00C 0.9500 . ?
C12 C21 1.514(3) . ?
C12 C24 1.519(3) . ?
C12 H00D 1.0000 . ?
C13 C14 1.379(3) . ?
C13 C22 1.517(3) . ?
C14 H00F 0.9500 . ?
C15 C23 1.519(3) . ?
C15 C19 1.520(3) . ?
C15 H00G 1.0000 . ?
C16 H00A 0.9800 . ?
C16 H00E 0.9800 . ?
C16 H00H 0.9800 . ?
C17 H00I 0.9800 . ?
C17 H00J 0.9800 . ?
C17 H00K 0.9800 . ?
C18 H00L 0.9800 . ?
C18 H00M 0.9800 . ?
C18 H00N 0.9800 . ?
C19 H00O 0.9800 . ?
C19 H00P 0.9800 . ?
C19 H00Q 0.9800 . ?
C20 H00R 0.9800 . ?
C20 H10 0.9800 . ?
C20 H00T 0.9800 . ?
C21 H00U 0.9800 . ?
C21 H00V 0.9800 . ?
C21 H00W 0.9800 . ?
C22 H7 0.9800 . ?
C22 H9 0.9800 . ?
C22 H8 0.9800 . ?
C23 H3 0.9800 . ?
C23 H1 0.9800 . ?
C23 H2 0.9800 . ?
C24 H6 0.9800 . ?
C24 H4 0.9800 . ?
C24 H5 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
C3 N1 C1 127.10(15) . . ?
C3 N1 H001 116.5 . . ?
C1 N1 H001 116.5 . . ?
C2 C1 C4 120.56(17) . . ?
C2 C1 N1 121.27(17) . . ?
C4 C1 N1 118.11(16) . . ?
C5 C2 C1 117.78(18) . . ?
C5 C2 C10 119.19(17) . . ?
C1 C2 C10 122.99(16) . . ?
C9 C3 C7 120.03(18) . . ?
C9 C3 N1 121.63(17) . . ?
C7 C3 N1 118.21(17) . . ?
C8 C4 C1 118.42(17) . . ?
C8 C4 C12 121.06(18) . . ?
C1 C4 C12 120.51(17) . . ?
C6 C5 C2 123.48(18) . . ?
C6 C5 H006 118.3 . . ?
C2 C5 H006 118.3 . . ?
C5 C6 C8 117.31(17) . . ?
C5 C6 C15 120.44(18) . . ?
C8 C6 C15 122.11(18) . . ?
C11 C7 C3 118.98(18) . . ?
C11 C7 C16 120.36(18) . . ?
C3 C7 C16 120.66(18) . . ?
C6 C8 C4 122.41(18) . . ?
C6 C8 H009 118.8 . . ?
C4 C8 H009 118.8 . . ?
C14 C9 C3 118.10(18) . . ?
C14 C9 C17 119.71(18) . . ?
C3 C9 C17 122.12(18) . . ?
C2 C10 C20 112.27(16) . . ?
C2 C10 C18 111.02(16) . . ?
C20 C10 C18 110.45(17) . . ?
C2 C10 H00B 107.6 . . ?
C20 C10 H00B 107.6 . . ?
C18 C10 H00B 107.6 . . ?
C13 C11 C7 122.61(19) . . ?
C13 C11 H00C 118.7 . . ?
C7 C11 H00C 118.7 . . ?
C21 C12 C4 111.88(16) . . ?
C21 C12 C24 109.55(18) . . ?
C4 C12 C24 114.21(17) . . ?
C21 C12 H00D 106.9 . . ?
C4 C12 H00D 106.9 . . ?
C24 C12 H00D 106.9 . . ?
C11 C13 C14 117.29(19) . . ?
C11 C13 C22 121.7(2) . . ?
C14 C13 C22 121.0(2) . . ?
C13 C14 C9 122.90(19) . . ?
C13 C14 H00F 118.5 . . ?
C9 C14 H00F 118.5 . . ?
C23 C15 C6 113.83(17) . . ?
C23 C15 C19 111.05(18) . . ?
C6 C15 C19 109.93(16) . . ?
C23 C15 H00G 107.2 . . ?
C6 C15 H00G 107.2 . . ?
C19 C15 H00G 107.2 . . ?
C7 C16 H00A 109.5 . . ?
C7 C16 H00E 109.5 . . ?
H00A C16 H00E 109.5 . . ?
C7 C16 H00H 109.5 . . ?
H00A C16 H00H 109.5 . . ?
H00E C16 H00H 109.5 . . ?
C9 C17 H00I 109.5 . . ?
C9 C17 H00J 109.5 . . ?
H00I C17 H00J 109.5 . . ?
C9 C17 H00K 109.5 . . ?
H00I C17 H00K 109.5 . . ?
H00J C17 H00K 109.5 . . ?
C10 C18 H00L 109.5 . . ?
C10 C18 H00M 109.5 . . ?
H00L C18 H00M 109.5 . . ?
C10 C18 H00N 109.5 . . ?
H00L C18 H00N 109.5 . . ?
H00M C18 H00N 109.5 . . ?
C15 C19 H00O 109.5 . . ?
C15 C19 H00P 109.5 . . ?
H00O C19 H00P 109.5 . . ?
C15 C19 H00Q 109.5 . . ?
H00O C19 H00Q 109.5 . . ?
H00P C19 H00Q 109.5 . . ?
C10 C20 H00R 109.5 . . ?
C10 C20 H10 109.5 . . ?
H00R C20 H10 109.5 . . ?
C10 C20 H00T 109.5 . . ?
H00R C20 H00T 109.5 . . ?
H10 C20 H00T 109.5 . . ?
C12 C21 H00U 109.5 . . ?
C12 C21 H00V 109.5 . . ?
H00U C21 H00V 109.5 . . ?
C12 C21 H00W 109.5 . . ?
H00U C21 H00W 109.5 . . ?
H00V C21 H00W 109.5 . . ?
C13 C22 H7 109.5 . . ?
C13 C22 H9 109.5 . . ?
H7 C22 H9 109.5 . . ?
C13 C22 H8 109.5 . . ?
H7 C22 H8 109.5 . . ?
H9 C22 H8 109.5 . . ?
C15 C23 H3 109.5 . . ?
C15 C23 H1 109.5 . . ?
H3 C23 H1 109.5 . . ?
C15 C23 H2 109.5 . . ?
H3 C23 H2 109.5 . . ?
H1 C23 H2 109.5 . . ?
C12 C24 H6 109.5 . . ?
C12 C24 H4 109.5 . . ?
H6 C24 H4 109.5 . . ?
C12 C24 H5 109.5 . . ?
H6 C24 H5 109.5 . . ?
H4 C24 H5 109.5 . . ?

_refine_diff_density_max         0.214
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.044

