# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_Compound2b
_database_code_depnum_ccdc_archive 'CCDC 1534569'
_audit_update_record             
;
2017-02-24 deposited with the CCDC.
2018-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            Compound1
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H30 N2 O2'
_chemical_formula_sum            'C16 H30 N2 O2'
_chemical_formula_weight         282.42

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   4.8725(17)
_cell_length_b                   5.548(3)
_cell_length_c                   16.422(6)
_cell_angle_alpha                85.972(12)
_cell_angle_beta                 89.944(8)
_cell_angle_gamma                64.398(8)
_cell_volume                     399.1(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1521
_cell_measurement_theta_min      3.72
_cell_measurement_theta_max      28.21

_exptl_crystal_description       'Rod shaped'
_exptl_crystal_colour            yellow
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_F_000             156
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   'multi-scan absorption correction'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6587
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.488
_diffrn_reflns_theta_max         28.337
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1999
_reflns_number_gt                1454
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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] 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         1999
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_ref         0.1741
_refine_ls_wR_factor_gt          0.1558
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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
O1 O 0.4542(2) 1.2093(2) 0.91927(7) 0.0174(3) Uani 1 1 d . . . . .
N1 N 0.0939(3) 1.0725(3) 0.88883(8) 0.0147(3) Uani 1 1 d . . . . .
H1 H -0.0897 1.0936 0.8960 0.018 Uiso 1 1 calc R U . . .
C1 C 0.1322(4) 0.1589(4) 0.56759(11) 0.0243(4) Uani 1 1 d . . . . .
H1A H 0.0413 0.0727 0.6038 0.036 Uiso 1 1 calc R U . . .
H1B H 0.2672 0.0313 0.5324 0.036 Uiso 1 1 calc R U . . .
H1C H -0.0245 0.3036 0.5352 0.036 Uiso 1 1 calc R U . . .
C2 C 0.3101(3) 0.2680(3) 0.61718(10) 0.0207(4) Uani 1 1 d . . . . .
H2A H 0.4715 0.1201 0.6485 0.025 Uiso 1 1 calc R U . . .
H2B H 0.4044 0.3517 0.5801 0.025 Uiso 1 1 calc R U . . .
C3 C 0.1141(3) 0.4709(3) 0.67503(10) 0.0176(4) Uani 1 1 d . . . . .
H3A H 0.0153 0.3886 0.7110 0.021 Uiso 1 1 calc R U . . .
H3B H -0.0438 0.6211 0.6435 0.021 Uiso 1 1 calc R U . . .
C4 C 0.2933(3) 0.5750(3) 0.72657(10) 0.0167(4) Uani 1 1 d . . . . .
H4A H 0.4490 0.4251 0.7588 0.020 Uiso 1 1 calc R U . . .
H4B H 0.3948 0.6546 0.6906 0.020 Uiso 1 1 calc R U . . .
C5 C 0.0968(3) 0.7810(3) 0.78338(9) 0.0151(4) Uani 1 1 d . . . . .
H5A H -0.0559 0.9337 0.7514 0.018 Uiso 1 1 calc R U . . .
H5B H -0.0080 0.7034 0.8190 0.018 Uiso 1 1 calc R U . . .
C6 C 0.2841(3) 0.8747(3) 0.83477(10) 0.0162(4) Uani 1 1 d . . . . .
H6A H 0.4362 0.7222 0.8670 0.019 Uiso 1 1 calc R U . . .
H6B H 0.3892 0.9520 0.7993 0.019 Uiso 1 1 calc R U . . .
C7 C 0.1963(3) 1.2230(3) 0.92780(9) 0.0136(4) Uani 1 1 d . . . . .
C8 C -0.0294(3) 1.4127(3) 0.98081(9) 0.0142(4) Uani 1 1 d . . . . .
H8 H -0.2170 1.4085 0.9872 0.017 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
O1 C7 1.2342(17) . ?
N1 C7 1.338(2) . ?
N1 C6 1.4518(19) . ?
N1 H1 0.8600 . ?
C1 C2 1.519(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.517(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.522(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.515(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.513(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.484(2) . ?
C8 C8 1.321(3) 2_587 ?
C8 H8 0.9300 . ?

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
C7 N1 C6 121.87(12) . . ?
C7 N1 H1 119.1 . . ?
C6 N1 H1 119.1 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 113.10(13) . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 C4 113.26(12) . . ?
C2 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C5 C4 C3 113.28(12) . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C4 111.64(12) . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
N1 C6 C5 111.27(12) . . ?
N1 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
N1 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
O1 C7 N1 123.02(14) . . ?
O1 C7 C8 122.73(14) . . ?
N1 C7 C8 114.24(13) . . ?
C8 C8 C7 121.68(17) 2_587 . ?
C8 C8 H8 119.2 2_587 . ?
C7 C8 H8 119.2 . . ?

_refine_diff_density_max         0.377
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.063

_shelxl_version_number           2013-3



####################################################################### 
# 
# 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_Compound3b
_database_code_depnum_ccdc_archive 'CCDC 1534571'
_audit_update_record             
;
2017-02-24 deposited with the CCDC.
2018-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            Compound3b
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H26 N2 O2'
_chemical_formula_sum            'C16 H26 N2 O2'
_chemical_formula_weight         278.39

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'
O O 0.0106 0.0060 '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                   12.621(5)
_cell_length_b                   6.553(3)
_cell_length_c                   9.876(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.417(11)
_cell_angle_gamma                90
_cell_volume                     770.3(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4240
_cell_measurement_theta_min      3.42
_cell_measurement_theta_max      25.37

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_F_000             304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.986
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   'multi-scan absorption correction'
_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            17792
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_av_R_equivalents  0.0944
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.423
_diffrn_reflns_theta_max         28.326
_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             1914
_reflns_number_gt                1203
_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)+(0.0635P)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         1914
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1438
_refine_ls_wR_factor_gt          0.1277
_refine_ls_goodness_of_fit_ref   1.212
_refine_ls_restrained_S_all      1.212
_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
O1 O 0.39073(10) -0.22514(17) 0.82758(10) 0.0468(4) Uani 1 1 d . . . . .
N1 N 0.36365(11) -0.14744(19) 1.03668(12) 0.0342(4) Uani 1 1 d . . . . .
H4 H 0.3829 -0.1750 1.1289 0.041 Uiso 1 1 calc R U . . .
C1 C 0.09055(15) 0.2695(3) 0.96819(17) 0.0487(5) Uani 1 1 d . . . . .
H1 H 0.0653 0.2077 1.0437 0.058 Uiso 1 1 calc R U . . .
H2 H 0.0398 0.3849 0.9255 0.058 Uiso 1 1 calc R U . . .
C2 C 0.08333(15) 0.1126(3) 0.85373(16) 0.0497(5) Uani 1 1 d . . . . .
H12 H 0.0992 0.1788 0.7724 0.060 Uiso 1 1 calc R U . . .
H11 H 0.0061 0.0566 0.8174 0.060 Uiso 1 1 calc R U . . .
C3 C 0.16618(13) -0.0603(3) 0.91134(17) 0.0432(5) Uani 1 1 d . . . . .
H6 H 0.1632 -0.1549 0.8320 0.052 Uiso 1 1 calc R U . . .
H3 H 0.1444 -0.1375 0.9842 0.052 Uiso 1 1 calc R U . . .
C4 C 0.28533(13) 0.0191(2) 0.97850(14) 0.0335(4) Uani 1 1 d . . . . .
H13 H 0.3078 0.0885 0.9020 0.040 Uiso 1 1 calc R U . . .
C5 C 0.40753(12) -0.2601(2) 0.95583(14) 0.0312(4) Uani 1 1 d . . . . .
C6 C 0.47777(12) -0.4335(2) 1.03304(14) 0.0333(4) Uani 1 1 d . . . . .
H5 H 0.4911 -0.4492 1.1330 0.040 Uiso 1 1 calc R U . . .
C7 C 0.20956(15) 0.3483(3) 1.03495(17) 0.0488(5) Uani 1 1 d . . . . .
H10 H 0.2126 0.4450 1.1131 0.059 Uiso 1 1 calc R U . . .
H9 H 0.2320 0.4227 0.9616 0.059 Uiso 1 1 calc R U . . .
C8 C 0.29128(14) 0.1739(2) 1.09483(16) 0.0395(4) Uani 1 1 d . . . . .
H8 H 0.3686 0.2285 1.1343 0.047 Uiso 1 1 calc R U . . .
H7 H 0.2728 0.1065 1.1739 0.047 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
O1 C5 1.2342(17) . ?
N1 C5 1.3353(18) . ?
N1 C4 1.4561(19) . ?
N1 H4 0.8800 . ?
C1 C2 1.508(2) . ?
C1 C7 1.516(2) . ?
C1 H1 0.9900 . ?
C1 H2 0.9900 . ?
C2 C3 1.518(2) . ?
C2 H12 0.9900 . ?
C2 H11 0.9900 . ?
C3 C4 1.519(2) . ?
C3 H6 0.9900 . ?
C3 H3 0.9900 . ?
C4 C8 1.516(2) . ?
C4 H13 1.0000 . ?
C5 C6 1.486(2) . ?
C6 C6 1.320(3) 3_647 ?
C6 H5 0.9500 . ?
C7 C8 1.521(2) . ?
C7 H10 0.9900 . ?
C7 H9 0.9900 . ?
C8 H8 0.9900 . ?
C8 H7 0.9900 . ?

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
C5 N1 C4 122.71(12) . . ?
C5 N1 H4 118.6 . . ?
C4 N1 H4 118.6 . . ?
C2 C1 C7 111.24(14) . . ?
C2 C1 H1 109.4 . . ?
C7 C1 H1 109.4 . . ?
C2 C1 H2 109.4 . . ?
C7 C1 H2 109.4 . . ?
H1 C1 H2 108.0 . . ?
C1 C2 C3 111.42(12) . . ?
C1 C2 H12 109.3 . . ?
C3 C2 H12 109.3 . . ?
C1 C2 H11 109.3 . . ?
C3 C2 H11 109.3 . . ?
H12 C2 H11 108.0 . . ?
C2 C3 C4 111.50(14) . . ?
C2 C3 H6 109.3 . . ?
C4 C3 H6 109.3 . . ?
C2 C3 H3 109.3 . . ?
C4 C3 H3 109.3 . . ?
H6 C3 H3 108.0 . . ?
N1 C4 C8 110.27(12) . . ?
N1 C4 C3 111.05(13) . . ?
C8 C4 C3 110.63(13) . . ?
N1 C4 H13 108.3 . . ?
C8 C4 H13 108.3 . . ?
C3 C4 H13 108.3 . . ?
O1 C5 N1 123.18(14) . . ?
O1 C5 C6 122.55(13) . . ?
N1 C5 C6 114.27(12) . . ?
C6 C6 C5 121.99(16) 3_647 . ?
C6 C6 H5 119.0 3_647 . ?
C5 C6 H5 119.0 . . ?
C1 C7 C8 111.05(14) . . ?
C1 C7 H10 109.4 . . ?
C8 C7 H10 109.4 . . ?
C1 C7 H9 109.4 . . ?
C8 C7 H9 109.4 . . ?
H10 C7 H9 108.0 . . ?
C4 C8 C7 110.59(12) . . ?
C4 C8 H8 109.5 . . ?
C7 C8 H8 109.5 . . ?
C4 C8 H7 109.5 . . ?
C7 C8 H7 109.5 . . ?
H8 C8 H7 108.1 . . ?

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
C7 C1 C2 C3 54.8(2) . . . . ?
C1 C2 C3 C4 -54.84(19) . . . . ?
C5 N1 C4 C8 -154.12(14) . . . . ?
C5 N1 C4 C3 82.88(17) . . . . ?
C2 C3 C4 N1 178.53(12) . . . . ?
C2 C3 C4 C8 55.75(17) . . . . ?
C4 N1 C5 O1 4.4(2) . . . . ?
C4 N1 C5 C6 -174.98(13) . . . . ?
O1 C5 C6 C6 -3.2(3) . . . 3_647 ?
N1 C5 C6 C6 176.18(18) . . . 3_647 ?
C2 C1 C7 C8 -55.99(18) . . . . ?
N1 C4 C8 C7 -179.91(13) . . . . ?
C3 C4 C8 C7 -56.66(18) . . . . ?
C1 C7 C8 C4 56.98(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H4 O1 0.88 2.04 2.9010(18) 166.0 4_556
N1 H4 O1 0.88 2.04 2.9010(18) 166.0 4_556

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.045



####################################################################### 
# 
# 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_Compound3a
_database_code_depnum_ccdc_archive 'CCDC 1534570'
_audit_update_record             
;
2017-02-24 deposited with the CCDC.
2018-01-05 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         'C16 H26 N2 O2'
_chemical_formula_sum            'C16 H26 N2 O2'
_chemical_formula_weight         278.39

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'
O O 0.0106 0.0060 '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                   9.9736(15)
_cell_length_b                   23.058(3)
_cell_length_c                   14.051(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.562(3)
_cell_angle_gamma                90
_cell_volume                     3231.2(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4039
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      21.36

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   'multi-scan absorption correction'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            59899
_diffrn_reflns_av_unetI/netI     0.0830
_diffrn_reflns_av_R_equivalents  0.1161
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.697
_diffrn_reflns_theta_max         28.402
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8077
_reflns_number_gt                4421
_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)+(0.1000P)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         8077
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1241
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_ref         0.1885
_refine_ls_wR_factor_gt          0.1439
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.972
_refine_ls_shift/su_max          0.001
_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
O1 O 0.05861(14) 0.13503(5) 0.90416(9) 0.0340(3) Uani 1 1 d . . . . .
O2 O 0.15940(15) -0.00967(6) 0.69823(10) 0.0398(4) Uani 1 1 d . . . . .
O3 O 0.16667(16) 1.02430(6) 0.18843(11) 0.0456(4) Uani 1 1 d . . . . .
O4 O 0.38773(17) 0.91851(7) 0.41047(10) 0.0492(4) Uani 1 1 d . . . . .
N1 N 0.07582(17) 0.10927(7) 1.05760(11) 0.0311(4) Uani 1 1 d . . . . .
H4 H 0.0912 0.0819 1.0978 0.037 Uiso 1 1 calc R U . . .
N2 N 0.09223(17) 0.08059(7) 0.73858(11) 0.0329(4) Uani 1 1 d . . . . .
H5 H 0.0642 0.1024 0.7839 0.039 Uiso 1 1 calc R U . . .
N3 N 0.32433(17) 0.93683(7) 0.56042(12) 0.0356(4) Uani 1 1 d . . . . .
H32 H 0.2741 0.9572 0.5970 0.043 Uiso 1 1 calc R U . . .
N4 N 0.31886(17) 0.95902(7) 0.23957(12) 0.0334(4) Uani 1 1 d . . . . .
H30 H 0.3544 0.9424 0.2885 0.040 Uiso 1 1 calc R U . . .
C1 C 0.0789(3) 0.26130(10) 1.23057(18) 0.0587(7) Uani 1 1 d . . . . .
H1 H 0.0539 0.2993 1.2540 0.070 Uiso 1 1 calc R U . . .
H3 H 0.1508 0.2466 1.2707 0.070 Uiso 1 1 calc R U . . .
C2 C 0.1276(3) 0.26659(9) 1.12936(17) 0.0495(6) Uani 1 1 d . . . . .
H21 H 0.2063 0.2913 1.1281 0.059 Uiso 1 1 calc R U . . .
H20 H 0.0584 0.2846 1.0904 0.059 Uiso 1 1 calc R U . . .
C3 C 0.1620(2) 0.20761(9) 1.08834(15) 0.0374(5) Uani 1 1 d . . . . .
H18 H 0.2370 0.1912 1.1236 0.045 Uiso 1 1 calc R U . . .
H19 H 0.1887 0.2120 1.0225 0.045 Uiso 1 1 calc R U . . .
C4 C 0.0425(2) 0.16665(8) 1.09356(14) 0.0299(4) Uani 1 1 d . . . . .
H22 H -0.0301 0.1826 1.0540 0.036 Uiso 1 1 calc R U . . .
C5 C 0.08349(19) 0.09750(8) 0.96484(13) 0.0279(4) Uani 1 1 d . . . . .
C6 C 0.1214(2) 0.03645(8) 0.94389(14) 0.0303(4) Uani 1 1 d . . . . .
H17 H 0.1371 0.0136 0.9974 0.036 Uiso 1 1 calc R U . . .
C7 C 0.1368(2) 0.00895(8) 0.86112(14) 0.0307(4) Uani 1 1 d . . . . .
H16 H 0.1566 -0.0302 0.8688 0.037 Uiso 1 1 calc R U . . .
C8 C 0.12948(19) 0.02668(8) 0.75948(14) 0.0301(4) Uani 1 1 d . . . . .
C9 C 0.0966(2) 0.10451(8) 0.64298(13) 0.0312(4) Uani 1 1 d . . . . .
H15 H 0.0749 0.0736 0.5976 0.037 Uiso 1 1 calc R U . . .
C10 C 0.2367(2) 0.12713(10) 0.62147(16) 0.0418(5) Uani 1 1 d . . . . .
H14 H 0.2999 0.0952 0.6240 0.050 Uiso 1 1 calc R U . . .
H13 H 0.2629 0.1551 0.6698 0.050 Uiso 1 1 calc R U . . .
C11 C 0.2430(2) 0.15578(11) 0.52384(18) 0.0485(6) Uani 1 1 d . . . . .
H12 H 0.3315 0.1721 0.5147 0.058 Uiso 1 1 calc R U . . .
H11 H 0.2277 0.1268 0.4748 0.058 Uiso 1 1 calc R U . . .
C12 C 0.1383(3) 0.20337(10) 0.51464(17) 0.0495(6) Uani 1 1 d . . . . .
H6 H 0.1594 0.2343 0.5590 0.059 Uiso 1 1 calc R U . . .
H2 H 0.1402 0.2193 0.4508 0.059 Uiso 1 1 calc R U . . .
C13 C -0.0405(3) 0.22099(10) 1.23605(19) 0.0579(7) Uani 1 1 d . . . . .
H26 H -0.1152 0.2376 1.2008 0.070 Uiso 1 1 calc R U . . .
H25 H -0.0672 0.2169 1.3019 0.070 Uiso 1 1 calc R U . . .
C14 C -0.0077(3) 0.16163(9) 1.19553(16) 0.0472(6) Uani 1 1 d . . . . .
H24 H -0.0873 0.1375 1.1965 0.057 Uiso 1 1 calc R U . . .
H23 H 0.0605 0.1432 1.2348 0.057 Uiso 1 1 calc R U . . .
C15 C -0.0009(2) 0.18018(11) 0.53482(17) 0.0493(6) Uani 1 1 d . . . . .
H10 H -0.0254 0.1519 0.4866 0.059 Uiso 1 1 calc R U . . .
H9 H -0.0651 0.2117 0.5313 0.059 Uiso 1 1 calc R U . . .
C16 C -0.0076(2) 0.15198(9) 0.63278(15) 0.0389(5) Uani 1 1 d . . . . .
H7 H 0.0074 0.1812 0.6815 0.047 Uiso 1 1 calc R U . . .
H8 H -0.0963 0.1357 0.6419 0.047 Uiso 1 1 calc R U . . .
C17 C 0.4919(3) 0.81359(10) 0.75523(16) 0.0454(6) Uani 1 1 d . . . . .
H38 H 0.4194 0.8176 0.8002 0.055 Uiso 1 1 calc R U . . .
H27 H 0.5552 0.7855 0.7807 0.055 Uiso 1 1 calc R U . . .
C18 C 0.4364(3) 0.79180(10) 0.66081(16) 0.0486(6) Uani 1 1 d . . . . .
H39 H 0.3875 0.7560 0.6709 0.058 Uiso 1 1 calc R U . . .
H40 H 0.5098 0.7836 0.6181 0.058 Uiso 1 1 calc R U . . .
C19 C 0.3434(2) 0.83653(9) 0.61555(16) 0.0415(5) Uani 1 1 d . . . . .
H41 H 0.3128 0.8225 0.5540 0.050 Uiso 1 1 calc R U . . .
H42 H 0.2655 0.8418 0.6554 0.050 Uiso 1 1 calc R U . . .
C20 C 0.4142(2) 0.89414(8) 0.60317(14) 0.0331(5) Uani 1 1 d . . . . .
H33 H 0.4900 0.8884 0.5604 0.040 Uiso 1 1 calc R U . . .
C21 C 0.3170(2) 0.94554(9) 0.46696(14) 0.0345(5) Uani 1 1 d . . . . .
C22 C 0.2138(2) 0.98915(9) 0.43827(15) 0.0377(5) Uani 1 1 d . . . . .
H31 H 0.1670 1.0052 0.4887 0.045 Uiso 1 1 calc R U . . .
C23 C 0.1769(2) 1.00907(9) 0.35292(15) 0.0354(5) Uani 1 1 d . . . . .
H43 H 0.1082 1.0363 0.3558 0.043 Uiso 1 1 calc R U . . .
C24 C 0.2217(2) 0.99736(8) 0.25370(15) 0.0328(5) Uani 1 1 d . . . . .
C25 C 0.3684(2) 0.94354(9) 0.14600(14) 0.0341(5) Uani 1 1 d . . . . .
H48 H 0.3662 0.9782 0.1056 0.041 Uiso 1 1 calc R U . . .
C26 C 0.5126(2) 0.92321(10) 0.15553(16) 0.0423(5) Uani 1 1 d . . . . .
H49 H 0.5178 0.8929 0.2033 0.051 Uiso 1 1 calc R U . . .
H50 H 0.5680 0.9553 0.1771 0.051 Uiso 1 1 calc R U . . .
C27 C 0.5674(2) 0.90008(11) 0.06186(18) 0.0521(6) Uani 1 1 d . . . . .
H52 H 0.5761 0.9318 0.0171 0.062 Uiso 1 1 calc R U . . .
H51 H 0.6559 0.8838 0.0729 0.062 Uiso 1 1 calc R U . . .
C28 C 0.4769(2) 0.85404(10) 0.01933(16) 0.0426(5) Uani 1 1 d . . . . .
H29 H 0.5117 0.8421 -0.0418 0.051 Uiso 1 1 calc R U . . .
H28 H 0.4761 0.8204 0.0608 0.051 Uiso 1 1 calc R U . . .
C29 C 0.5616(2) 0.87166(9) 0.74342(17) 0.0452(6) Uani 1 1 d . . . . .
H37 H 0.6400 0.8668 0.7039 0.054 Uiso 1 1 calc R U . . .
H36 H 0.5914 0.8857 0.8052 0.054 Uiso 1 1 calc R U . . .
C30 C 0.4682(2) 0.91602(9) 0.69803(16) 0.0412(5) Uani 1 1 d . . . . .
H35 H 0.3941 0.9237 0.7404 0.049 Uiso 1 1 calc R U . . .
H34 H 0.5163 0.9521 0.6884 0.049 Uiso 1 1 calc R U . . .
C31 C 0.2807(2) 0.89741(11) 0.10066(17) 0.0474(6) Uani 1 1 d . . . . .
H47 H 0.1915 0.9130 0.0902 0.057 Uiso 1 1 calc R U . . .
H46 H 0.2733 0.8648 0.1439 0.057 Uiso 1 1 calc R U . . .
C32 C 0.3362(3) 0.87640(12) 0.00650(18) 0.0578(7) Uani 1 1 d . . . . .
H44 H 0.2795 0.8457 -0.0187 0.069 Uiso 1 1 calc R U . . .
H45 H 0.3359 0.9081 -0.0389 0.069 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
O1 C5 1.238(2) . ?
O2 C8 1.240(2) . ?
O3 C24 1.232(2) . ?
O4 C21 1.236(2) . ?
N1 C5 1.334(2) . ?
N1 C4 1.456(2) . ?
N1 H4 0.8600 . ?
N2 C8 1.329(2) . ?
N2 C9 1.453(2) . ?
N2 H5 0.8600 . ?
N3 C21 1.330(3) . ?
N3 C20 1.457(2) . ?
N3 H32 0.8600 . ?
N4 C24 1.328(3) . ?
N4 C25 1.454(2) . ?
N4 H30 0.8600 . ?
C1 C2 1.512(3) . ?
C1 C13 1.513(4) . ?
C1 H1 0.9700 . ?
C1 H3 0.9700 . ?
C2 C3 1.518(3) . ?
C2 H21 0.9700 . ?
C2 H20 0.9700 . ?
C3 C4 1.523(3) . ?
C3 H18 0.9700 . ?
C3 H19 0.9700 . ?
C4 C14 1.527(3) . ?
C4 H22 0.9800 . ?
C5 C6 1.488(3) . ?
C6 C7 1.335(3) . ?
C6 H17 0.9300 . ?
C7 C8 1.487(3) . ?
C7 H16 0.9300 . ?
C9 C16 1.515(3) . ?
C9 C10 1.524(3) . ?
C9 H15 0.9800 . ?
C10 C11 1.524(3) . ?
C10 H14 0.9700 . ?
C10 H13 0.9700 . ?
C11 C12 1.519(3) . ?
C11 H12 0.9700 . ?
C11 H11 0.9700 . ?
C12 C15 1.518(3) . ?
C12 H6 0.9700 . ?
C12 H2 0.9700 . ?
C13 C14 1.519(3) . ?
C13 H26 0.9700 . ?
C13 H25 0.9700 . ?
C14 H24 0.9700 . ?
C14 H23 0.9700 . ?
C15 C16 1.524(3) . ?
C15 H10 0.9700 . ?
C15 H9 0.9700 . ?
C16 H7 0.9700 . ?
C16 H8 0.9700 . ?
C17 C29 1.518(3) . ?
C17 C18 1.519(3) . ?
C17 H38 0.9700 . ?
C17 H27 0.9700 . ?
C18 C19 1.522(3) . ?
C18 H39 0.9700 . ?
C18 H40 0.9700 . ?
C19 C20 1.515(3) . ?
C19 H41 0.9700 . ?
C19 H42 0.9700 . ?
C20 C30 1.519(3) . ?
C20 H33 0.9800 . ?
C21 C22 1.492(3) . ?
C22 C23 1.332(3) . ?
C22 H31 0.9300 . ?
C23 C24 1.493(3) . ?
C23 H43 0.9300 . ?
C25 C31 1.514(3) . ?
C25 C26 1.517(3) . ?
C25 H48 0.9800 . ?
C26 C27 1.526(3) . ?
C26 H49 0.9700 . ?
C26 H50 0.9700 . ?
C27 C28 1.513(3) . ?
C27 H52 0.9700 . ?
C27 H51 0.9700 . ?
C28 C32 1.504(3) . ?
C28 H29 0.9700 . ?
C28 H28 0.9700 . ?
C29 C30 1.520(3) . ?
C29 H37 0.9700 . ?
C29 H36 0.9700 . ?
C30 H35 0.9700 . ?
C30 H34 0.9700 . ?
C31 C32 1.519(3) . ?
C31 H47 0.9700 . ?
C31 H46 0.9700 . ?
C32 H44 0.9700 . ?
C32 H45 0.9700 . ?

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
C5 N1 C4 122.65(16) . . ?
C5 N1 H4 118.7 . . ?
C4 N1 H4 118.7 . . ?
C8 N2 C9 123.25(16) . . ?
C8 N2 H5 118.4 . . ?
C9 N2 H5 118.4 . . ?
C21 N3 C20 122.47(16) . . ?
C21 N3 H32 118.8 . . ?
C20 N3 H32 118.8 . . ?
C24 N4 C25 123.62(17) . . ?
C24 N4 H30 118.2 . . ?
C25 N4 H30 118.2 . . ?
C2 C1 C13 110.9(2) . . ?
C2 C1 H1 109.4 . . ?
C13 C1 H1 109.4 . . ?
C2 C1 H3 109.4 . . ?
C13 C1 H3 109.4 . . ?
H1 C1 H3 108.0 . . ?
C1 C2 C3 111.16(19) . . ?
C1 C2 H21 109.4 . . ?
C3 C2 H21 109.4 . . ?
C1 C2 H20 109.4 . . ?
C3 C2 H20 109.4 . . ?
H21 C2 H20 108.0 . . ?
C2 C3 C4 110.91(18) . . ?
C2 C3 H18 109.5 . . ?
C4 C3 H18 109.5 . . ?
C2 C3 H19 109.5 . . ?
C4 C3 H19 109.5 . . ?
H18 C3 H19 108.0 . . ?
N1 C4 C3 111.41(16) . . ?
N1 C4 C14 109.57(16) . . ?
C3 C4 C14 110.86(17) . . ?
N1 C4 H22 108.3 . . ?
C3 C4 H22 108.3 . . ?
C14 C4 H22 108.3 . . ?
O1 C5 N1 121.16(17) . . ?
O1 C5 C6 125.07(17) . . ?
N1 C5 C6 113.76(16) . . ?
C7 C6 C5 130.80(18) . . ?
C7 C6 H17 114.6 . . ?
C5 C6 H17 114.6 . . ?
C6 C7 C8 134.54(18) . . ?
C6 C7 H16 112.7 . . ?
C8 C7 H16 112.7 . . ?
O2 C8 N2 123.19(18) . . ?
O2 C8 C7 118.10(17) . . ?
N2 C8 C7 118.71(17) . . ?
N2 C9 C16 109.57(16) . . ?
N2 C9 C10 110.43(17) . . ?
C16 C9 C10 111.31(17) . . ?
N2 C9 H15 108.5 . . ?
C16 C9 H15 108.5 . . ?
C10 C9 H15 108.5 . . ?
C9 C10 C11 111.88(19) . . ?
C9 C10 H14 109.2 . . ?
C11 C10 H14 109.2 . . ?
C9 C10 H13 109.2 . . ?
C11 C10 H13 109.2 . . ?
H14 C10 H13 107.9 . . ?
C12 C11 C10 110.80(19) . . ?
C12 C11 H12 109.5 . . ?
C10 C11 H12 109.5 . . ?
C12 C11 H11 109.5 . . ?
C10 C11 H11 109.5 . . ?
H12 C11 H11 108.1 . . ?
C15 C12 C11 111.03(19) . . ?
C15 C12 H6 109.4 . . ?
C11 C12 H6 109.4 . . ?
C15 C12 H2 109.4 . . ?
C11 C12 H2 109.4 . . ?
H6 C12 H2 108.0 . . ?
C1 C13 C14 111.2(2) . . ?
C1 C13 H26 109.4 . . ?
C14 C13 H26 109.4 . . ?
C1 C13 H25 109.4 . . ?
C14 C13 H25 109.4 . . ?
H26 C13 H25 108.0 . . ?
C13 C14 C4 110.92(18) . . ?
C13 C14 H24 109.5 . . ?
C4 C14 H24 109.5 . . ?
C13 C14 H23 109.5 . . ?
C4 C14 H23 109.5 . . ?
H24 C14 H23 108.0 . . ?
C12 C15 C16 111.5(2) . . ?
C12 C15 H10 109.3 . . ?
C16 C15 H10 109.3 . . ?
C12 C15 H9 109.3 . . ?
C16 C15 H9 109.3 . . ?
H10 C15 H9 108.0 . . ?
C9 C16 C15 110.94(17) . . ?
C9 C16 H7 109.5 . . ?
C15 C16 H7 109.5 . . ?
C9 C16 H8 109.5 . . ?
C15 C16 H8 109.5 . . ?
H7 C16 H8 108.0 . . ?
C29 C17 C18 111.10(18) . . ?
C29 C17 H38 109.4 . . ?
C18 C17 H38 109.4 . . ?
C29 C17 H27 109.4 . . ?
C18 C17 H27 109.4 . . ?
H38 C17 H27 108.0 . . ?
C17 C18 C19 110.88(19) . . ?
C17 C18 H39 109.5 . . ?
C19 C18 H39 109.5 . . ?
C17 C18 H40 109.5 . . ?
C19 C18 H40 109.5 . . ?
H39 C18 H40 108.1 . . ?
C20 C19 C18 111.10(19) . . ?
C20 C19 H41 109.4 . . ?
C18 C19 H41 109.4 . . ?
C20 C19 H42 109.4 . . ?
C18 C19 H42 109.4 . . ?
H41 C19 H42 108.0 . . ?
N3 C20 C19 110.76(17) . . ?
N3 C20 C30 110.42(16) . . ?
C19 C20 C30 110.61(17) . . ?
N3 C20 H33 108.3 . . ?
C19 C20 H33 108.3 . . ?
C30 C20 H33 108.3 . . ?
O4 C21 N3 122.15(19) . . ?
O4 C21 C22 124.27(19) . . ?
N3 C21 C22 113.56(17) . . ?
C23 C22 C21 131.22(19) . . ?
C23 C22 H31 114.4 . . ?
C21 C22 H31 114.4 . . ?
C22 C23 C24 134.10(19) . . ?
C22 C23 H43 113.0 . . ?
C24 C23 H43 113.0 . . ?
O3 C24 N4 123.01(19) . . ?
O3 C24 C23 117.95(19) . . ?
N4 C24 C23 119.04(18) . . ?
N4 C25 C31 110.66(17) . . ?
N4 C25 C26 109.06(17) . . ?
C31 C25 C26 111.30(17) . . ?
N4 C25 H48 108.6 . . ?
C31 C25 H48 108.6 . . ?
C26 C25 H48 108.6 . . ?
C25 C26 C27 112.29(19) . . ?
C25 C26 H49 109.1 . . ?
C27 C26 H49 109.1 . . ?
C25 C26 H50 109.1 . . ?
C27 C26 H50 109.1 . . ?
H49 C26 H50 107.9 . . ?
C28 C27 C26 111.60(18) . . ?
C28 C27 H52 109.3 . . ?
C26 C27 H52 109.3 . . ?
C28 C27 H51 109.3 . . ?
C26 C27 H51 109.3 . . ?
H52 C27 H51 108.0 . . ?
C32 C28 C27 111.1(2) . . ?
C32 C28 H29 109.4 . . ?
C27 C28 H29 109.4 . . ?
C32 C28 H28 109.4 . . ?
C27 C28 H28 109.4 . . ?
H29 C28 H28 108.0 . . ?
C17 C29 C30 111.10(19) . . ?
C17 C29 H37 109.4 . . ?
C30 C29 H37 109.4 . . ?
C17 C29 H36 109.4 . . ?
C30 C29 H36 109.4 . . ?
H37 C29 H36 108.0 . . ?
C20 C30 C29 110.82(18) . . ?
C20 C30 H35 109.5 . . ?
C29 C30 H35 109.5 . . ?
C20 C30 H34 109.5 . . ?
C29 C30 H34 109.5 . . ?
H35 C30 H34 108.1 . . ?
C25 C31 C32 112.13(19) . . ?
C25 C31 H47 109.2 . . ?
C32 C31 H47 109.2 . . ?
C25 C31 H46 109.2 . . ?
C32 C31 H46 109.2 . . ?
H47 C31 H46 107.9 . . ?
C28 C32 C31 110.7(2) . . ?
C28 C32 H44 109.5 . . ?
C31 C32 H44 109.5 . . ?
C28 C32 H45 109.5 . . ?
C31 C32 H45 109.5 . . ?
H44 C32 H45 108.1 . . ?

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
C13 C1 C2 C3 -56.6(3) . . . . ?
C1 C2 C3 C4 56.3(3) . . . . ?
C5 N1 C4 C3 -77.5(2) . . . . ?
C5 N1 C4 C14 159.49(19) . . . . ?
C2 C3 C4 N1 -177.91(18) . . . . ?
C2 C3 C4 C14 -55.6(2) . . . . ?
C4 N1 C5 O1 -2.0(3) . . . . ?
C4 N1 C5 C6 178.92(17) . . . . ?
O1 C5 C6 C7 -0.1(4) . . . . ?
N1 C5 C6 C7 178.9(2) . . . . ?
C5 C6 C7 C8 3.2(4) . . . . ?
C9 N2 C8 O2 -6.9(3) . . . . ?
C9 N2 C8 C7 172.61(17) . . . . ?
C6 C7 C8 O2 174.7(2) . . . . ?
C6 C7 C8 N2 -4.9(3) . . . . ?
C8 N2 C9 C16 153.08(19) . . . . ?
C8 N2 C9 C10 -84.0(2) . . . . ?
N2 C9 C10 C11 -176.66(17) . . . . ?
C16 C9 C10 C11 -54.7(2) . . . . ?
C9 C10 C11 C12 54.9(3) . . . . ?
C10 C11 C12 C15 -55.5(3) . . . . ?
C2 C1 C13 C14 56.4(3) . . . . ?
C1 C13 C14 C4 -55.8(3) . . . . ?
N1 C4 C14 C13 178.7(2) . . . . ?
C3 C4 C14 C13 55.4(3) . . . . ?
C11 C12 C15 C16 56.4(3) . . . . ?
N2 C9 C16 C15 177.09(18) . . . . ?
C10 C9 C16 C15 54.7(2) . . . . ?
C12 C15 C16 C9 -55.9(3) . . . . ?
C29 C17 C18 C19 -55.5(3) . . . . ?
C17 C18 C19 C20 56.2(3) . . . . ?
C21 N3 C20 C19 -92.5(2) . . . . ?
C21 N3 C20 C30 144.6(2) . . . . ?
C18 C19 C20 N3 -179.61(17) . . . . ?
C18 C19 C20 C30 -56.8(2) . . . . ?
C20 N3 C21 O4 -1.1(3) . . . . ?
C20 N3 C21 C22 177.15(18) . . . . ?
O4 C21 C22 C23 -1.5(4) . . . . ?
N3 C21 C22 C23 -179.8(2) . . . . ?
C21 C22 C23 C24 -0.6(4) . . . . ?
C25 N4 C24 O3 -1.6(3) . . . . ?
C25 N4 C24 C23 178.84(18) . . . . ?
C22 C23 C24 O3 -179.1(2) . . . . ?
C22 C23 C24 N4 0.4(4) . . . . ?
C24 N4 C25 C31 -83.8(2) . . . . ?
C24 N4 C25 C26 153.45(19) . . . . ?
N4 C25 C26 C27 173.96(17) . . . . ?
C31 C25 C26 C27 51.6(3) . . . . ?
C25 C26 C27 C28 -52.9(3) . . . . ?
C26 C27 C28 C32 55.6(3) . . . . ?
C18 C17 C29 C30 55.7(3) . . . . ?
N3 C20 C30 C29 179.75(18) . . . . ?
C19 C20 C30 C29 56.8(2) . . . . ?
C17 C29 C30 C20 -56.3(3) . . . . ?
N4 C25 C31 C32 -175.05(19) . . . . ?
C26 C25 C31 C32 -53.6(3) . . . . ?
C27 C28 C32 C31 -57.2(3) . . . . ?
C25 C31 C32 C28 56.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H30 O4 0.86 1.83 2.660(2) 162.4 .
N3 H32 O2 0.86 1.99 2.835(2) 168.6 1_565
N2 H5 O1 0.86 1.85 2.668(2) 157.8 .
N1 H4 O3 0.86 1.98 2.830(2) 167.8 1_546
N4 H30 O4 0.86 1.83 2.660(2) 162.4 .
N2 H5 O1 0.86 1.85 2.668(2) 157.8 .
N1 H4 O3 0.86 1.98 2.830(2) 167.8 1_546
N2 H5 O1 0.86 1.85 2.668(2) 157.8 .
N3 H32 O2 0.86 1.99 2.835(2) 168.6 1_565
N4 H30 O4 0.86 1.83 2.660(2) 162.4 .
N1 H4 O3 0.86 1.98 2.830(2) 167.8 1_546
N2 H5 O1 0.86 1.85 2.668(2) 157.8 .
N3 H32 O2 0.86 1.99 2.835(2) 168.6 1_565
N4 H30 O4 0.86 1.83 2.660(2) 162.4 .

_refine_diff_density_max         0.196
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.052



