# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_pca2_a
_database_code_depnum_ccdc_archive 'CCDC 1866029'
_audit_update_record             
;
2018-09-05 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;
_audit_creation_date             2018-07-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        DBN-CO2
_chemical_formula_moiety         'C8 H12 N2 O2'
_chemical_formula_sum            'C8 H12 N2 O2'
_chemical_formula_weight         168.20
_chemical_absolute_configuration rm
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   13.4813(4)
_cell_length_b                   8.2397(3)
_cell_length_c                   6.9346(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     770.31(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5271
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.939
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8531
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1585 before and 0.0390 after correction. The Ratio of minimum to maximum transmission is 0.8531. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.137
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10967
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.404
_diffrn_reflns_theta_min         2.472
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.844
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                1851
_reflns_number_total             1901
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2007)'
_refine_diff_density_max         0.552
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 
;
 Flack x determined using 831 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1901
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.120
_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)+(0.0683P)²+0.2489P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1162
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H3A(0.024) H3B(0.024) H4A(0.039) H4B(0.039) H5A(0.029) H5B(0.029)
 H6A(0.023) H6B(0.023) H7A(0.026) H7B(0.026) H8A(0.024) H8B(0.024)
 Fixed X: H3A(-0.651) H3B(-0.6547) H4A(-0.7181) H4B(-0.6722) H5A(-0.5774) H5B(-
 0.5601) H6A(-0.3221) H6B(-0.3096) H7A(-0.2506) H7B(-0.3366) H8A(-0.3744) H8B(-
 0.3648)
 Fixed Y: H3A(-0.6038) H3B(-0.6066) H4A(-0.8599) H4B(-0.8766) H5A(-0.9507)
 H5B(-1.0374) H6A(-0.5633) H6B(-0.5065) H7A(-0.7771) H7B(-0.7706) H8A(-0.9831)
 H8B(-0.8631)
 Fixed Z: H3A(-0.6283) H3B(-0.3958) H4A(-0.4367) H4B(-0.6502) H5A(-0.2942)
 H5B(-0.5001) H6A(-0.3774) H6B(-0.5968) H7A(-0.5476) H7B(-0.7074) H8A(-0.4935)
 H8B(-0.3116)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O1 O -0.57411(14) -0.3459(2) -0.5406(3) 0.0288(4) Uani 1 1 d . . . . .
O2 O -0.41257(16) -0.2797(2) -0.5201(4) 0.0355(5) Uani 1 1 d . . . . .
N1 N -0.45313(12) -0.54774(19) -0.5215(3) 0.0151(4) Uani 1 1 d . . . . .
N2 N -0.48714(14) -0.8210(2) -0.4741(3) 0.0163(4) Uani 1 1 d . . . . .
C1 C -0.48420(18) -0.3714(2) -0.5282(3) 0.0222(5) Uani 1 1 d . . . . .
C2 C -0.51678(15) -0.6703(2) -0.5050(3) 0.0152(4) Uani 1 1 d . . . . .
C3 C -0.62788(14) -0.6616(3) -0.5115(4) 0.0202(4) Uani 1 1 d . . . . .
H3A H -0.6510 -0.6038 -0.6283 0.024 Uiso 1 1 calc R . . . .
H3B H -0.6547 -0.6066 -0.3958 0.024 Uiso 1 1 calc R . . . .
C4 C -0.65832(18) -0.8412(3) -0.5164(6) 0.0325(6) Uani 1 1 d . . . . .
H4A H -0.7181 -0.8599 -0.4367 0.039 Uiso 1 1 calc R . . . .
H4B H -0.6722 -0.8766 -0.6502 0.039 Uiso 1 1 calc R . . . .
C5 C -0.56969(18) -0.9319(3) -0.4344(4) 0.0242(5) Uani 1 1 d . . . . .
H5A H -0.5774 -0.9507 -0.2942 0.029 Uiso 1 1 calc R . . . .
H5B H -0.5601 -1.0374 -0.5001 0.029 Uiso 1 1 calc R . . . .
C6 C -0.34555(14) -0.5822(3) -0.5108(4) 0.0190(4) Uani 1 1 d . . . . .
H6A H -0.3221 -0.5633 -0.3774 0.023 Uiso 1 1 calc R . . . .
H6B H -0.3096 -0.5065 -0.5968 0.023 Uiso 1 1 calc R . . . .
C7 C -0.32195(16) -0.7548(3) -0.5687(3) 0.0216(5) Uani 1 1 d . . . . .
H7A H -0.2506 -0.7771 -0.5476 0.026 Uiso 1 1 calc R . . . .
H7B H -0.3366 -0.7706 -0.7074 0.026 Uiso 1 1 calc R . . . .
C8 C -0.38396(17) -0.8699(3) -0.4492(3) 0.0197(5) Uani 1 1 d . . . . .
H8A H -0.3744 -0.9831 -0.4935 0.024 Uiso 1 1 calc R . . . .
H8B H -0.3648 -0.8631 -0.3116 0.024 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.233(3) . ?
O2 C1 1.228(3) . ?
N1 C1 1.513(3) . ?
N1 C2 1.330(3) . ?
N1 C6 1.480(2) . ?
N2 C2 1.322(3) . ?
N2 C5 1.466(3) . ?
N2 C8 1.459(3) . ?
C2 C3 1.500(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.536(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.519(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.512(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.512(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 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
C2 N1 C1 123.58(18) . . ?
C2 N1 C6 118.84(17) . . ?
C6 N1 C1 117.21(17) . . ?
C2 N2 C5 112.72(19) . . ?
C2 N2 C8 124.57(18) . . ?
C8 N2 C5 121.96(19) . . ?
O1 C1 N1 116.0(2) . . ?
O2 C1 O1 132.2(2) . . ?
O2 C1 N1 111.8(2) . . ?
N1 C2 C3 127.26(18) . . ?
N2 C2 N1 122.14(19) . . ?
N2 C2 C3 110.58(18) . . ?
C2 C3 H3A 111.2 . . ?
C2 C3 H3B 111.2 . . ?
C2 C3 C4 102.80(17) . . ?
H3A C3 H3B 109.1 . . ?
C4 C3 H3A 111.2 . . ?
C4 C3 H3B 111.2 . . ?
C3 C4 H4A 110.8 . . ?
C3 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
C5 C4 C3 104.78(19) . . ?
C5 C4 H4A 110.8 . . ?
C5 C4 H4B 110.8 . . ?
N2 C5 C4 102.73(19) . . ?
N2 C5 H5A 111.2 . . ?
N2 C5 H5B 111.2 . . ?
C4 C5 H5A 111.2 . . ?
C4 C5 H5B 111.2 . . ?
H5A C5 H5B 109.1 . . ?
N1 C6 H6A 109.2 . . ?
N1 C6 H6B 109.2 . . ?
N1 C6 C7 111.93(17) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C6 C7 H7A 109.8 . . ?
C6 C7 H7B 109.8 . . ?
C6 C7 C8 109.16(18) . . ?
H7A C7 H7B 108.3 . . ?
C8 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
N2 C8 C7 106.77(17) . . ?
N2 C8 H8A 110.4 . . ?
N2 C8 H8B 110.4 . . ?
C7 C8 H8A 110.4 . . ?
C7 C8 H8B 110.4 . . ?
H8A C8 H8B 108.6 . . ?

_olex2_date_sample_data_collection 2018-02-28
_olex2_date_sample_submission    2018-02-28
_olex2_submission_original_sample_id lw180228
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_p2_1-n_a
_database_code_depnum_ccdc_archive 'CCDC 1866031'
_audit_update_record             
;
2018-09-05 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;
_audit_creation_date             2018-07-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H23 N3 O2'
_chemical_formula_sum            'C13 H23 N3 O2'
_chemical_formula_weight         253.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.99820(10)
_cell_length_b                   9.27850(10)
_cell_length_c                   14.3717(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.7140(10)
_cell_angle_gamma                90
_cell_volume                     1411.77(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4663
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.64
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8531
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1525 before and 0.0381 after correction. The Ratio of minimum to maximum transmission is 0.8531. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.321
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.056
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14415
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.292
_diffrn_reflns_theta_min         2.082
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2846
_reflns_number_total             3503
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2007)'
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         3503
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.054
_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)+(0.0459P)²+0.5520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1038
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H4(0.018) H3(0.018) H5A(0.031) H5B(0.031) H5C(0.031) H7A(0.032)
 H7B(0.032) H7C(0.032) H8A(0.03) H8B(0.03) H8C(0.03) H9A(0.036) H9B(0.036)
 H9C(0.036) H13A(0.037) H13B(0.037) H13C(0.037) H12A(0.038) H12B(0.038)
 H12C(0.038) H11A(0.037) H11B(0.037) H11C(0.037)
 Fixed X: H4(0.4737) H3(0.687) H5A(0.8703) H5B(0.7478) H5C(0.7428) H7A(0.8782)
 H7B(1.0069) H7C(0.8773) H8A(0.921) H8B(1.0502) H8C(0.9621) H9A(0.9161)
 H9B(1.0273) H9C(0.8923) H13A(0.3237) H13B(0.2761) H13C(0.3866) H12A(0.516)
 H12B(0.4) H12C(0.5373) H11A(0.4654) H11B(0.325) H11C(0.3756)
 Fixed Y: H4(0.1563) H3(0.1546) H5A(0.157) H5B(0.066) H5C(0.1727) H7A(0.2118)
 H7B(0.285) H7C(0.3734) H8A(0.4105) H8B(0.3292) H8C(0.2708) H9A(0.0272)
 H9B(0.0589) H9C(0.0057) H13A(0.1394) H13B(0.1461) H13C(0.0372) H12A(0.1515)
 H12B(0.2576) H12C(0.3223) H11A(0.4691) H11B(0.4209) H11C(0.3978)
 Fixed Z: H4(0.184) H3(0.1594) H5A(0.5569) H5B(0.503) H5C(0.5894) H7A(0.1702)
 H7B(0.2312) H7C(0.2091) H8A(0.3959) H8B(0.3983) H8C(0.4623) H9A(0.3919)
 H9B(0.3424) H9C(0.2779) H13A(0.2513) H13B(0.3471) H13C(0.3411) H12A(0.4969)
 H12B(0.4928) H12C(0.5007) H11A(0.3511) H11B(0.349) H11C(0.2556)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O1 O 0.71513(8) 0.51329(9) 0.43009(6) 0.01697(19) Uani 1 1 d . . . . .
O2 O 0.80793(8) 0.43977(10) 0.58304(6) 0.0175(2) Uani 1 1 d . . . . .
N2 N 0.75101(10) 0.21987(10) 0.30343(7) 0.0132(2) Uani 1 1 d . . . . .
N1 N 0.73722(10) 0.27484(10) 0.46526(7) 0.0142(2) Uani 1 1 d . . . . .
N3 N 0.56205(10) 0.21881(10) 0.32624(6) 0.0129(2) Uani 1 1 d . . . . .
C1 C 0.75526(11) 0.42289(12) 0.49558(8) 0.0134(2) Uani 1 1 d . . . . .
C2 C 0.68539(11) 0.24278(12) 0.36943(8) 0.0124(2) Uani 1 1 d . . . . .
C4 C 0.55019(12) 0.17914(12) 0.23113(8) 0.0148(2) Uani 1 1 d . . . . .
H4 H 0.4737 0.1563 0.1840 0.018 Uiso 1 1 calc R . . . .
C3 C 0.66652(12) 0.17879(13) 0.21762(8) 0.0150(2) Uani 1 1 d . . . . .
H3 H 0.6870 0.1546 0.1594 0.018 Uiso 1 1 calc R . . . .
C10 C 0.44777(12) 0.24866(13) 0.36322(8) 0.0152(2) Uani 1 1 d . . . . .
C6 C 0.89238(12) 0.22048(13) 0.31708(9) 0.0159(2) Uani 1 1 d . . . . .
C5 C 0.77786(13) 0.15812(13) 0.53428(8) 0.0205(3) Uani 1 1 d . . . . .
H5A H 0.8703 0.1570 0.5569 0.031 Uiso 1 1 calc GR . . . .
H5B H 0.7478 0.0660 0.5030 0.031 Uiso 1 1 calc GR . . . .
H5C H 0.7428 0.1727 0.5894 0.031 Uiso 1 1 calc GR . . . .
C7 C 0.91581(13) 0.27784(14) 0.22344(9) 0.0215(3) Uani 1 1 d . . . . .
H7A H 0.8782 0.2118 0.1702 0.032 Uiso 1 1 calc GR . . . .
H7B H 1.0069 0.2850 0.2312 0.032 Uiso 1 1 calc GR . . . .
H7C H 0.8773 0.3734 0.2091 0.032 Uiso 1 1 calc GR . . . .
C8 C 0.96273(13) 0.31634(14) 0.40094(9) 0.0203(3) Uani 1 1 d . . . . .
H8A H 0.9210 0.4105 0.3959 0.030 Uiso 1 1 calc GR . . . .
H8B H 1.0502 0.3292 0.3983 0.030 Uiso 1 1 calc GR . . . .
H8C H 0.9621 0.2708 0.4623 0.030 Uiso 1 1 calc GR . . . .
C9 C 0.93592(14) 0.06409(14) 0.33383(10) 0.0242(3) Uani 1 1 d . . . . .
H9A H 0.9161 0.0272 0.3919 0.036 Uiso 1 1 calc GR . . . .
H9B H 1.0273 0.0589 0.3424 0.036 Uiso 1 1 calc GR . . . .
H9C H 0.8923 0.0057 0.2779 0.036 Uiso 1 1 calc GR . . . .
C13 C 0.34979(13) 0.13244(16) 0.32200(9) 0.0250(3) Uani 1 1 d . . . . .
H13A H 0.3237 0.1394 0.2513 0.037 Uiso 1 1 calc GR . . . .
H13B H 0.2761 0.1461 0.3471 0.037 Uiso 1 1 calc GR . . . .
H13C H 0.3866 0.0372 0.3411 0.037 Uiso 1 1 calc GR . . . .
C12 C 0.47795(14) 0.24467(17) 0.47324(9) 0.0257(3) Uani 1 1 d . . . . .
H12A H 0.5160 0.1515 0.4969 0.038 Uiso 1 1 calc GR . . . .
H12B H 0.4000 0.2576 0.4928 0.038 Uiso 1 1 calc GR . . . .
H12C H 0.5373 0.3223 0.5007 0.038 Uiso 1 1 calc GR . . . .
C11 C 0.39911(14) 0.39735(15) 0.32647(10) 0.0244(3) Uani 1 1 d . . . . .
H11A H 0.4654 0.4691 0.3511 0.037 Uiso 1 1 calc GR . . . .
H11B H 0.3250 0.4209 0.3490 0.037 Uiso 1 1 calc GR . . . .
H11C H 0.3756 0.3978 0.2556 0.037 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2487(14) . ?
O2 C1 1.2432(14) . ?
N2 C2 1.3552(14) . ?
N2 C3 1.3817(15) . ?
N2 C6 1.5134(16) . ?
N1 C1 1.4385(15) . ?
N1 C2 1.3729(14) . ?
N1 C5 1.4548(15) . ?
N3 C2 1.3486(16) . ?
N3 C4 1.3872(13) . ?
N3 C10 1.5168(14) . ?
C4 H4 0.9500 . ?
C4 C3 1.3451(17) . ?
C3 H3 0.9500 . ?
C10 C13 1.5262(18) . ?
C10 C12 1.5256(16) . ?
C10 C11 1.5217(18) . ?
C6 C7 1.5326(16) . ?
C6 C8 1.5288(17) . ?
C6 C9 1.5265(17) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
C2 N2 C3 108.13(10) . . ?
C2 N2 C6 129.18(10) . . ?
C3 N2 C6 122.39(9) . . ?
C1 N1 C5 120.84(9) . . ?
C2 N1 C1 119.77(9) . . ?
C2 N1 C5 119.34(10) . . ?
C2 N3 C4 108.16(9) . . ?
C2 N3 C10 129.37(9) . . ?
C4 N3 C10 121.87(10) . . ?
O1 C1 N1 114.93(10) . . ?
O2 C1 O1 130.56(11) . . ?
O2 C1 N1 114.51(10) . . ?
N2 C2 N1 125.52(11) . . ?
N3 C2 N2 108.18(10) . . ?
N3 C2 N1 126.15(10) . . ?
N3 C4 H4 126.2 . . ?
C3 C4 N3 107.68(10) . . ?
C3 C4 H4 126.2 . . ?
N2 C3 H3 126.1 . . ?
C4 C3 N2 107.85(10) . . ?
C4 C3 H3 126.1 . . ?
N3 C10 C13 107.46(9) . . ?
N3 C10 C12 112.98(10) . . ?
N3 C10 C11 106.90(9) . . ?
C12 C10 C13 108.53(10) . . ?
C11 C10 C13 111.15(11) . . ?
C11 C10 C12 109.82(11) . . ?
N2 C6 C7 107.37(10) . . ?
N2 C6 C8 112.78(9) . . ?
N2 C6 C9 106.52(10) . . ?
C8 C6 C7 108.70(10) . . ?
C9 C6 C7 110.39(10) . . ?
C9 C6 C8 111.01(11) . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_olex2_date_sample_data_collection 2017-10-12
_olex2_date_sample_submission    2017-10-12
_olex2_submission_original_sample_id lw171012
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_p21c
_database_code_depnum_ccdc_archive 'CCDC 1866033'
_audit_update_record             
;
2018-09-05 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;
_audit_creation_date             2018-07-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H21 N3 O2'
_chemical_formula_sum            'C12 H21 N3 O2'
_chemical_formula_weight         239.32
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.36320(10)
_cell_length_b                   18.2488(2)
_cell_length_c                   8.12900(10)
_cell_angle_alpha                90
_cell_angle_beta                 114.8120(7)
_cell_angle_gamma                90
_cell_volume                     1260.76(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8740
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.535
_cell_measurement_theta_min      2.978
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0991 before and 0.0298 after correction.
The Ratio of minimum to maximum transmission is 0.9029.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            20780
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.555
_diffrn_reflns_theta_min         3.010
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3122
_reflns_number_total             3523
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.433
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3523
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.096
_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)+(0.0498P)²+0.5785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1115
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Others
 Fixed Sof: C5(0.75) H5(0.75) C5A(0.25) H5A(0.25) C6A(0.25) H6AA(0.25)
 H6AB(0.25) H6AC(0.25) C6(0.75) H6A(0.75) H6B(0.75) H6C(0.75) H7AA(0.75)
 H7AB(0.75) H7AC(0.75) H7BD(0.25) H7BE(0.25) H7BF(0.25)
 Fixed Uiso: H5(0.014) H5A(0.028) H6AA(0.044) H6AB(0.044) H6AC(0.044)
 H6A(0.028) H6B(0.028) H6C(0.028) H7AA(0.031) H7AB(0.031) H7AC(0.031)
 H7BD(0.031) H7BE(0.031) H7BF(0.031) H8A(0.028) H8B(0.028) H8C(0.028) H9A(0.03)
 H9B(0.03) H9C(0.03) H10(0.017) H11A(0.025) H11B(0.025) H11C(0.025) H12A(0.029)
 H12B(0.029) H12C(0.029)
 Fixed X: H5(0.9009) H5A(0.9791) H6AA(0.9419) H6AB(1.1105) H6AC(0.9806)
 H6A(0.9826) H6B(1.1255) H6C(1.0659) H7AA(0.9871) H7AB(1.0796) H7AC(0.9024)
 H7BD(0.9357) H7BE(1.0913) H7BF(0.93) H8A(0.6757) H8B(0.5152) H8C(0.6807)
 H9A(0.2758) H9B(0.3145) H9C(0.2829) H10(0.5629) H11A(0.5114) H11B(0.3686)
 H11C(0.3485) H12A(0.2671) H12B(0.3195) H12C(0.3999)
 Fixed Y: H5(0.2833) H5A(0.3997) H6AA(0.25) H6AB(0.2871) H6AC(0.2908)
 H6A(0.2973) H6B(0.2967) H6C(0.3726) H7AA(0.4336) H7AB(0.3669) H7AC(0.3845)
 H7BD(0.4336) H7BE(0.3843) H7BF(0.3504) H8A(0.2362) H8B(0.2732) H8C(0.3074)
 H9A(0.3876) H9B(0.3049) H9C(0.3246) H10(0.4724) H11A(0.3601) H11B(0.4141)
 H11C(0.353) H12A(0.4649) H12B(0.5249) H12C(0.5237)
 Fixed Z: H5(0.7855) H5A(0.6705) H6AA(0.7084) H6AB(0.7626) H6AC(0.5576)
 H6A(0.5411) H6B(0.7384) H6C(0.633) H7AA(0.8655) H7AB(0.9935) H7AC(0.9614)
 H7BD(0.9034) H7BE(0.9737) H7BF(0.9631) H8A(0.7578) H8B(0.7411) H8C(0.8751)
 H9A(0.4088) H9B(0.4796) H9C(0.2753) H10(0.1784) H11A(0.0345) H11B(-0.0768)
 H11C(0.0532) H12A(0.1979) H12B(0.0905) H12C(0.3074)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O1 O 0.80958(10) 0.36829(5) 0.20009(11) 0.02075(19) Uani 1 1 d . . . . .
O2 O 0.99956(10) 0.45493(5) 0.30219(11) 0.01953(18) Uani 1 1 d . . . . .
N1 N 0.82228(11) 0.44636(5) 0.42386(13) 0.0176(2) Uani 1 1 d . . . A 2
H1 H 0.883(2) 0.4778(10) 0.508(2) 0.033(4) Uiso 1 1 d . . . . .
N2 N 0.75903(10) 0.35866(5) 0.60680(12) 0.01547(19) Uani 1 1 d . . . . .
N3 N 0.56309(10) 0.40233(5) 0.36960(11) 0.01112(17) Uani 1 1 d . . . . .
C1 C 0.88179(12) 0.42067(6) 0.29731(14) 0.0145(2) Uani 1 1 d . . . . .
C2 C 0.72109(12) 0.40356(6) 0.46353(13) 0.0137(2) Uani 1 1 d . . . . .
C3 C 0.62252(12) 0.33046(6) 0.60930(14) 0.0138(2) Uani 1 1 d . . . . .
C4 C 0.49977(12) 0.35665(5) 0.45982(13) 0.01201(19) Uani 1 1 d . . . . .
C5 C 0.9161(2) 0.33266(10) 0.7421(2) 0.0117(3) Uani 0.75 1 d . . P B 1
H5 H 0.9009 0.2833 0.7855 0.014 Uiso 0.75 1 calc R . P B 1
C5A C 0.9377(7) 0.3605(4) 0.7249(9) 0.0230(12) Uani 0.25 1 d . . P B 2
H5A H 0.9791 0.3997 0.6705 0.028 Uiso 0.25 1 calc R . P B 2
C6A C 0.9977(7) 0.2913(4) 0.6851(8) 0.0296(12) Uani 0.25 1 d . . P B 2
H6AA H 0.9419 0.2500 0.7084 0.044 Uiso 0.25 1 calc GR . P B 2
H6AB H 1.1105 0.2871 0.7626 0.044 Uiso 0.25 1 calc GR . P B 2
H6AC H 0.9806 0.2908 0.5576 0.044 Uiso 0.25 1 calc GR . P B 2
C6 C 1.03312(19) 0.32403(11) 0.6558(2) 0.0190(3) Uani 0.75 1 d . . P B 1
H6A H 0.9826 0.2973 0.5411 0.028 Uiso 0.75 1 calc GR . P B 1
H6B H 1.1255 0.2967 0.7384 0.028 Uiso 0.75 1 calc GR . P B 1
H6C H 1.0659 0.3726 0.6330 0.028 Uiso 0.75 1 calc GR . P B 1
C7 C 0.97669(13) 0.38402(7) 0.90522(15) 0.0205(2) Uani 1 1 d . . . . .
H7AA H 0.9871 0.4336 0.8655 0.031 Uiso 0.75 1 calc R . P B 1
H7AB H 1.0796 0.3669 0.9935 0.031 Uiso 0.75 1 calc R . P B 1
H7AC H 0.9024 0.3845 0.9614 0.031 Uiso 0.75 1 calc R . P B 1
H7BD H 0.9357 0.4336 0.9034 0.031 Uiso 0.25 1 calc R . P B 2
H7BE H 1.0913 0.3843 0.9737 0.031 Uiso 0.25 1 calc R . P B 2
H7BF H 0.9300 0.3504 0.9631 0.031 Uiso 0.25 1 calc R . P B 2
C8 C 0.62361(14) 0.28272(6) 0.75864(15) 0.0189(2) Uani 1 1 d . . . . .
H8A H 0.6757 0.2362 0.7578 0.028 Uiso 1 1 calc GR . . . .
H8B H 0.5152 0.2732 0.7411 0.028 Uiso 1 1 calc GR . . . .
H8C H 0.6807 0.3074 0.8751 0.028 Uiso 1 1 calc GR . . . .
C9 C 0.32854(13) 0.34221(7) 0.40081(16) 0.0201(2) Uani 1 1 d . . . . .
H9A H 0.2758 0.3876 0.4088 0.030 Uiso 1 1 calc GR . . . .
H9B H 0.3145 0.3049 0.4796 0.030 Uiso 1 1 calc GR . . . .
H9C H 0.2829 0.3246 0.2753 0.030 Uiso 1 1 calc GR . . . .
C10 C 0.48181(12) 0.44140(6) 0.19473(13) 0.0138(2) Uani 1 1 d . . . . .
H10 H 0.5629 0.4724 0.1784 0.017 Uiso 1 1 calc R . . . .
C11 C 0.42226(13) 0.38729(6) 0.03738(14) 0.0166(2) Uani 1 1 d . . . . .
H11A H 0.5114 0.3601 0.0345 0.025 Uiso 1 1 calc GR . . . .
H11B H 0.3686 0.4141 -0.0768 0.025 Uiso 1 1 calc GR . . . .
H11C H 0.3485 0.3530 0.0532 0.025 Uiso 1 1 calc GR . . . .
C12 C 0.35587(13) 0.49334(6) 0.19790(15) 0.0193(2) Uani 1 1 d . . . . .
H12A H 0.2671 0.4649 0.1979 0.029 Uiso 1 1 calc GR . . . .
H12B H 0.3195 0.5249 0.0905 0.029 Uiso 1 1 calc GR . . . .
H12C H 0.3999 0.5237 0.3074 0.029 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2437(13) . ?
O2 C1 1.2536(13) . ?
N1 C1 1.4386(13) . ?
N1 C2 1.3668(14) . ?
N2 C2 1.3441(14) . ?
N2 C3 1.3859(14) . ?
N2 C5 1.497(2) . ?
N2 C5A 1.541(6) . ?
N3 C2 1.3506(13) . ?
N3 C4 1.3962(13) . ?
N3 C10 1.4832(13) . ?
C3 C4 1.3615(14) . ?
C3 C8 1.4907(15) . ?
C4 C9 1.4915(14) . ?
C5 C6 1.537(2) . ?
C5 C7 1.525(2) . ?
C5A C6A 1.472(9) . ?
C5A C7 1.420(7) . ?
C10 C11 1.5243(14) . ?
C10 C12 1.5215(15) . ?

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 C1 119.83(9) . . ?
C2 N2 C3 109.21(8) . . ?
C2 N2 C5 130.61(11) . . ?
C2 N2 C5A 110.4(3) . . ?
C3 N2 C5 119.96(11) . . ?
C3 N2 C5A 140.0(3) . . ?
C2 N3 C4 108.58(8) . . ?
C2 N3 C10 122.25(9) . . ?
C4 N3 C10 129.07(8) . . ?
O1 C1 O2 129.78(10) . . ?
O1 C1 N1 115.74(9) . . ?
O2 C1 N1 114.48(9) . . ?
N2 C2 N1 126.55(9) . . ?
N2 C2 N3 107.96(9) . . ?
N3 C2 N1 125.40(10) . . ?
N2 C3 C8 122.53(9) . . ?
C4 C3 N2 107.15(9) . . ?
C4 C3 C8 130.29(10) . . ?
N3 C4 C9 124.94(9) . . ?
C3 C4 N3 107.03(9) . . ?
C3 C4 C9 128.02(10) . . ?
N2 C5 C6 111.46(13) . . ?
N2 C5 C7 109.65(12) . . ?
C7 C5 C6 112.54(14) . . ?
C6A C5A N2 105.0(5) . . ?
C7 C5A N2 113.1(4) . . ?
C7 C5A C6A 122.0(5) . . ?
N3 C10 C11 110.66(8) . . ?
N3 C10 C12 111.89(8) . . ?
C12 C10 C11 113.86(9) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_p212121_neu
_database_code_depnum_ccdc_archive 'CCDC 1866032'
_audit_update_record             
;
2018-09-05 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;
_audit_creation_date             2016-01-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H19 N3'
_chemical_formula_sum            'C13 H19 N3'
_chemical_formula_weight         217.31
_chemical_absolute_configuration .
_chemical_melting_point          ?
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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.9385(2)
_cell_length_b                   10.0425(2)
_cell_length_c                   24.7502(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2470.25(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9738
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.591
_cell_measurement_theta_min      2.884
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1206 before and 0.0311 after correction.
The Ratio of minimum to maximum transmission is 0.9440.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            34800
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.604
_diffrn_reflns_theta_min         2.612
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.783
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                6692
_reflns_number_total             6911
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 2885 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         6911
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.064
_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)+(0.0655P)²+0.9793P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1212
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C21(H21), C24(H24), C8(H8), C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C20(H20), C4(H4A), C5(H5), C6(H6), C7(H7)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,
 H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
N4 N 0.33684(19) 0.89874(19) 0.47294(7) 0.0241(4) Uani 1 1 d . . . . .
H4 H 0.327(3) 0.803(3) 0.4641(13) 0.033(8) Uiso 1 1 d . . . . .
N5 N 0.4658(2) 1.03663(17) 0.52980(7) 0.0230(3) Uani 1 1 d . . . . .
N6 N 0.50312(16) 0.81950(16) 0.53742(6) 0.0165(3) Uani 1 1 d . . . . .
C14 C 0.4274(2) 0.9137(2) 0.51000(8) 0.0200(4) Uani 1 1 d . . . . .
C15 C 0.5655(2) 1.0200(2) 0.56906(7) 0.0211(4) Uani 1 1 d . . . . .
C16 C 0.58722(19) 0.88225(19) 0.57447(7) 0.0172(3) Uani 1 1 d . . . . .
C17 C 0.67688(19) 0.8303(2) 0.61190(8) 0.0200(4) Uani 1 1 d . . . . .
H17 H 0.6893 0.7371 0.6160 0.024 Uiso 1 1 calc R . . . .
C18 C 0.7484(2) 0.9229(2) 0.64338(8) 0.0259(4) Uani 1 1 d . . . . .
H18 H 0.8111 0.8918 0.6695 0.031 Uiso 1 1 calc R . . . .
C19 C 0.7290(2) 1.0593(2) 0.63698(9) 0.0301(5) Uani 1 1 d . . . . .
H19 H 0.7802 1.1193 0.6584 0.036 Uiso 1 1 calc R . . . .
C20 C 0.6367(2) 1.1106(2) 0.59994(9) 0.0278(4) Uani 1 1 d . . . . .
H20 H 0.6233 1.2038 0.5961 0.033 Uiso 1 1 calc R . . . .
C21 C 0.3911(2) 1.1573(2) 0.51424(9) 0.0264(4) Uani 1 1 d . . . . .
H21 H 0.3173 1.1281 0.4895 0.032 Uiso 1 1 calc R . . . .
C22 C 0.4774(3) 1.2526(3) 0.48273(11) 0.0389(6) Uani 1 1 d . . . . .
H22A H 0.4216 1.3254 0.4689 0.058 Uiso 1 1 calc GR . . . .
H22B H 0.5194 1.2055 0.4524 0.058 Uiso 1 1 calc GR . . . .
H22C H 0.5475 1.2889 0.5064 0.058 Uiso 1 1 calc GR . . . .
C23 C 0.3243(3) 1.2195(2) 0.56305(10) 0.0315(5) Uani 1 1 d . . . . .
H23A H 0.3934 1.2490 0.5886 0.047 Uiso 1 1 calc GR . . . .
H23B H 0.2660 1.1536 0.5805 0.047 Uiso 1 1 calc GR . . . .
H23C H 0.2703 1.2960 0.5516 0.047 Uiso 1 1 calc GR . . . .
C24 C 0.49270(19) 0.67478(18) 0.53072(7) 0.0180(3) Uani 1 1 d . . . . .
H24 H 0.5645 0.6346 0.5538 0.022 Uiso 1 1 calc R . . . .
C25 C 0.3589(2) 0.6215(2) 0.55181(9) 0.0275(4) Uani 1 1 d . . . . .
H25A H 0.3453 0.6517 0.5891 0.041 Uiso 1 1 calc GR . . . .
H25B H 0.3599 0.5239 0.5509 0.041 Uiso 1 1 calc GR . . . .
H25C H 0.2855 0.6546 0.5291 0.041 Uiso 1 1 calc GR . . . .
C26 C 0.5222(2) 0.6311(2) 0.47267(8) 0.0241(4) Uani 1 1 d . . . . .
H26A H 0.4421 0.6451 0.4503 0.036 Uiso 1 1 calc GR . . . .
H26B H 0.5465 0.5366 0.4723 0.036 Uiso 1 1 calc GR . . . .
H26C H 0.5970 0.6838 0.4582 0.036 Uiso 1 1 calc GR . . . .
N1 N 0.65448(16) 0.45200(16) 0.61029(6) 0.0162(3) Uani 1 1 d . . . . .
H1 H 0.717(3) 0.474(3) 0.5895(12) 0.028(7) Uiso 1 1 d . . . . .
N2 N 0.81685(15) 0.47050(17) 0.68363(6) 0.0162(3) Uani 1 1 d . . . . .
N3 N 0.60257(15) 0.42496(16) 0.70230(6) 0.0154(3) Uani 1 1 d . . . . .
C1 C 0.69116(18) 0.44994(17) 0.65991(7) 0.0140(3) Uani 1 1 d . . . . .
C2 C 0.80585(18) 0.45994(18) 0.73969(7) 0.0156(3) Uani 1 1 d . . . . .
C3 C 0.67036(17) 0.43159(17) 0.75146(7) 0.0144(3) Uani 1 1 d . . . . .
C4 C 0.62680(19) 0.41565(19) 0.80428(7) 0.0178(3) Uani 1 1 d . . . . .
H4A H 0.5353 0.3966 0.8123 0.021 Uiso 1 1 calc R . . . .
C5 C 0.7226(2) 0.4287(2) 0.84532(7) 0.0193(4) Uani 1 1 d . . . . .
H5 H 0.6956 0.4175 0.8819 0.023 Uiso 1 1 calc R . . . .
C6 C 0.8564(2) 0.4578(2) 0.83390(8) 0.0218(4) Uani 1 1 d . . . . .
H6 H 0.9190 0.4662 0.8627 0.026 Uiso 1 1 calc R . . . .
C7 C 0.90000(19) 0.4748(2) 0.78056(7) 0.0201(4) Uani 1 1 d . . . . .
H7 H 0.9911 0.4958 0.7727 0.024 Uiso 1 1 calc R . . . .
C8 C 0.94203(19) 0.4826(2) 0.65252(7) 0.0186(3) Uani 1 1 d . . . . .
H8 H 0.9168 0.4772 0.6135 0.022 Uiso 1 1 calc R . . . .
C9 C 1.0084(2) 0.6173(2) 0.66095(10) 0.0277(4) Uani 1 1 d . . . . .
H9A H 1.0330 0.6275 0.6991 0.042 Uiso 1 1 calc GR . . . .
H9B H 0.9456 0.6881 0.6507 0.042 Uiso 1 1 calc GR . . . .
H9C H 1.0895 0.6232 0.6385 0.042 Uiso 1 1 calc GR . . . .
C10 C 1.0356(2) 0.3653(2) 0.66391(8) 0.0237(4) Uani 1 1 d . . . . .
H10A H 1.0632 0.3671 0.7019 0.036 Uiso 1 1 calc GR . . . .
H10B H 1.1153 0.3718 0.6408 0.036 Uiso 1 1 calc GR . . . .
H10C H 0.9883 0.2817 0.6564 0.036 Uiso 1 1 calc GR . . . .
C11 C 0.45722(18) 0.41029(18) 0.69290(7) 0.0159(3) Uani 1 1 d . . . . .
H11 H 0.4437 0.4101 0.6529 0.019 Uiso 1 1 calc R . . . .
C12 C 0.3804(2) 0.52924(19) 0.71489(9) 0.0225(4) Uani 1 1 d . . . . .
H12A H 0.3932 0.5347 0.7541 0.034 Uiso 1 1 calc GR . . . .
H12B H 0.2844 0.5189 0.7069 0.034 Uiso 1 1 calc GR . . . .
H12C H 0.4139 0.6109 0.6979 0.034 Uiso 1 1 calc GR . . . .
C13 C 0.4055(2) 0.27735(19) 0.71374(8) 0.0207(4) Uani 1 1 d . . . . .
H13A H 0.4597 0.2051 0.6984 0.031 Uiso 1 1 calc GR . . . .
H13B H 0.3113 0.2660 0.7030 0.031 Uiso 1 1 calc GR . . . .
H13C H 0.4124 0.2753 0.7532 0.031 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N4 C14 1.294(3) . ?
N5 C14 1.382(3) . ?
N5 C15 1.398(3) . ?
N5 C21 1.472(3) . ?
N6 C14 1.386(2) . ?
N6 C16 1.392(2) . ?
N6 C24 1.466(2) . ?
C15 C16 1.406(3) . ?
C15 C20 1.383(3) . ?
C16 C17 1.387(3) . ?
C17 C18 1.406(3) . ?
C18 C19 1.393(4) . ?
C19 C20 1.395(4) . ?
C21 C22 1.503(3) . ?
C21 C23 1.513(3) . ?
C24 C25 1.526(3) . ?
C24 C26 1.531(3) . ?
N1 C1 1.281(2) . ?
N2 C1 1.396(2) . ?
N2 C2 1.396(2) . ?
N2 C8 1.468(2) . ?
N3 C1 1.393(2) . ?
N3 C3 1.392(2) . ?
N3 C11 1.471(2) . ?
C2 C3 1.407(2) . ?
C2 C7 1.386(2) . ?
C3 C4 1.386(2) . ?
C4 C5 1.398(3) . ?
C5 C6 1.390(3) . ?
C6 C7 1.400(3) . ?
C8 C9 1.519(3) . ?
C8 C10 1.527(3) . ?
C11 C12 1.519(3) . ?
C11 C13 1.521(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 N5 C15 109.57(16) . . ?
C14 N5 C21 120.24(18) . . ?
C15 N5 C21 129.61(18) . . ?
C14 N6 C16 109.85(16) . . ?
C14 N6 C24 125.64(16) . . ?
C16 N6 C24 124.45(15) . . ?
N4 C14 N5 123.17(18) . . ?
N4 C14 N6 130.19(19) . . ?
N5 C14 N6 106.64(17) . . ?
N5 C15 C16 107.03(17) . . ?
C20 C15 N5 131.9(2) . . ?
C20 C15 C16 121.1(2) . . ?
N6 C16 C15 106.88(17) . . ?
C17 C16 N6 130.98(18) . . ?
C17 C16 C15 122.13(18) . . ?
C16 C17 C18 116.52(19) . . ?
C19 C18 C17 121.2(2) . . ?
C18 C19 C20 121.9(2) . . ?
C15 C20 C19 117.2(2) . . ?
N5 C21 C22 111.8(2) . . ?
N5 C21 C23 110.60(18) . . ?
C22 C21 C23 113.7(2) . . ?
N6 C24 C25 111.75(16) . . ?
N6 C24 C26 112.10(15) . . ?
C25 C24 C26 112.82(17) . . ?
C1 N2 C2 109.69(14) . . ?
C1 N2 C8 123.37(14) . . ?
C2 N2 C8 126.44(15) . . ?
C1 N3 C3 110.12(14) . . ?
C1 N3 C11 121.32(14) . . ?
C3 N3 C11 128.20(15) . . ?
N1 C1 N2 130.97(17) . . ?
N1 C1 N3 123.04(16) . . ?
N3 C1 N2 106.00(14) . . ?
N2 C2 C3 107.23(15) . . ?
C7 C2 N2 131.64(17) . . ?
C7 C2 C3 121.11(16) . . ?
N3 C3 C2 106.96(15) . . ?
C4 C3 N3 131.87(17) . . ?
C4 C3 C2 121.17(16) . . ?
C3 C4 C5 117.48(17) . . ?
C6 C5 C4 121.55(17) . . ?
C5 C6 C7 120.90(17) . . ?
C2 C7 C6 117.77(18) . . ?
N2 C8 C9 111.70(17) . . ?
N2 C8 C10 110.82(16) . . ?
C9 C8 C10 113.39(17) . . ?
N3 C11 C12 111.00(15) . . ?
N3 C11 C13 111.47(15) . . ?
C12 C11 C13 113.53(16) . . ?

####################################################################### 
# 
# 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_p21n_a
_database_code_depnum_ccdc_archive 'CCDC 1866030'
_audit_update_record             
;
2018-09-05 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;
_audit_creation_date             2018-07-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        '[DBNH][HCO3]'
_chemical_formula_moiety         'C7 H13 N2, C H O3'
_chemical_formula_sum            'C8 H14 N2 O3'
_chemical_formula_weight         186.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.7428(6)
_cell_length_b                   11.1556(9)
_cell_length_c                   10.4925(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.8440(10)
_cell_angle_gamma                90
_cell_volume                     895.52(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2505
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.68
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0667 before and 0.0261 after correction. The Ratio of minimum to maximum transmission is 0.9103. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.075
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0145
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.949
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4119
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.384
_diffrn_reflns_theta_min         2.682
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.949
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1594
_reflns_number_total             1726
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2007)'
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1726
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.043
_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)+(0.0428P)²+0.5408P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.0977
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H3A(0.035) H3B(0.035) H4A(0.032) H4B(0.032) H5A(0.041) H5B(0.041)
 H6A(0.026) H6B(0.026) H7A(0.025) H7B(0.025) H8A(0.026) H8B(0.026)
 Fixed X: H3A(0.4393) H3B(0.6249) H4A(0.4453) H4B(0.6464) H5A(0.7171)
 H5B(0.5206) H6A(0.9105) H6B(0.7447) H7A(0.818) H7B(0.6182) H8A(0.713)
 H8B(0.8891)
 Fixed Y: H3A(0.183) H3B(0.1213) H4A(0.0843) H4B(0.0469) H5A(0.1858)
 H5B(0.238) H6A(0.4646) H6B(0.5361) H7A(0.5859) H7B(0.5473) H8A(0.4432)
 H8B(0.4012)
 Fixed Z: H3A(0.549) H3B(0.6016) H4A(0.364) H4B(0.4068) H5A(0.2701)
 H5B(0.2471) H6A(0.624) H6B(0.659) H7A(0.4487) H7B(0.4455) H8A(0.278)
 H8B(0.3682)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
N1 N 0.69533(16) 0.36128(10) 0.61878(11) 0.0192(3) Uani 1 1 d . . . . .
H1 H 0.668(3) 0.3325(18) 0.703(2) 0.046(5) Uiso 1 1 d . . . . .
N2 N 0.67393(16) 0.31110(10) 0.40304(11) 0.0200(3) Uani 1 1 d . . . . .
C2 C 0.65019(18) 0.28877(12) 0.52193(13) 0.0187(3) Uani 1 1 d . . . . .
C3 C 0.5606(2) 0.17130(13) 0.53215(14) 0.0290(4) Uani 1 1 d . . . . .
H3A H 0.4393 0.1830 0.5490 0.035 Uiso 1 1 calc R . . . .
H3B H 0.6249 0.1213 0.6016 0.035 Uiso 1 1 calc R . . . .
C4 C 0.5629(2) 0.11462(13) 0.39993(14) 0.0271(3) Uani 1 1 d . . . . .
H4A H 0.4453 0.0843 0.3640 0.032 Uiso 1 1 calc R . . . .
H4B H 0.6464 0.0469 0.4068 0.032 Uiso 1 1 calc R . . . .
C5 C 0.6191(3) 0.21312(14) 0.31343(14) 0.0340(4) Uani 1 1 d . . . . .
H5A H 0.7171 0.1858 0.2701 0.041 Uiso 1 1 calc R . . . .
H5B H 0.5206 0.2380 0.2471 0.041 Uiso 1 1 calc R . . . .
C6 C 0.7826(2) 0.47493(12) 0.60081(13) 0.0216(3) Uani 1 1 d . . . . .
H6A H 0.9105 0.4646 0.6240 0.026 Uiso 1 1 calc R . . . .
H6B H 0.7447 0.5361 0.6590 0.026 Uiso 1 1 calc R . . . .
C7 C 0.74027(19) 0.51809(12) 0.46194(13) 0.0209(3) Uani 1 1 d . . . . .
H7A H 0.8180 0.5859 0.4487 0.025 Uiso 1 1 calc R . . . .
H7B H 0.6182 0.5473 0.4455 0.025 Uiso 1 1 calc R . . . .
C8 C 0.7633(2) 0.41828(12) 0.36651(13) 0.0217(3) Uani 1 1 d . . . . .
H8A H 0.7130 0.4432 0.2780 0.026 Uiso 1 1 calc R . . . .
H8B H 0.8891 0.4012 0.3682 0.026 Uiso 1 1 calc R . . . .
O1 O 0.57914(16) 0.46995(9) 0.86848(10) 0.0296(3) Uani 1 1 d . . . . .
O2 O 0.62534(15) 0.27435(9) 0.84718(10) 0.0274(3) Uani 1 1 d . . . . .
O3 O 0.52379(16) 0.33986(10) 1.01989(10) 0.0289(3) Uani 1 1 d . . . . .
H3 H 0.492(3) 0.409(2) 1.053(2) 0.057(7) Uiso 1 1 d . . . . .
C1 C 0.57838(19) 0.36283(12) 0.90638(13) 0.0204(3) 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
N1 H1 0.99(2) . ?
N1 C2 1.3038(18) . ?
N1 C6 1.4622(17) . ?
N2 C2 1.3125(17) . ?
N2 C5 1.4615(18) . ?
N2 C8 1.4618(17) . ?
C2 C3 1.4945(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.527(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.531(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5217(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5261(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
O1 C1 1.2598(17) . ?
O2 C1 1.2497(17) . ?
O3 H3 0.90(2) . ?
O3 C1 1.3482(16) . ?

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 H1 115.1(12) . . ?
C2 N1 C6 120.75(11) . . ?
C6 N1 H1 124.2(12) . . ?
C2 N2 C5 113.60(11) . . ?
C2 N2 C8 123.06(11) . . ?
C5 N2 C8 123.05(11) . . ?
N1 C2 N2 124.27(13) . . ?
N1 C2 C3 124.05(12) . . ?
N2 C2 C3 111.66(12) . . ?
C2 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
C2 C3 C4 103.15(12) . . ?
H3A C3 H3B 109.1 . . ?
C4 C3 H3A 111.1 . . ?
C4 C3 H3B 111.1 . . ?
C3 C4 H4A 110.4 . . ?
C3 C4 H4B 110.4 . . ?
C3 C4 C5 106.60(12) . . ?
H4A C4 H4B 108.6 . . ?
C5 C4 H4A 110.4 . . ?
C5 C4 H4B 110.4 . . ?
N2 C5 C4 103.67(12) . . ?
N2 C5 H5A 111.0 . . ?
N2 C5 H5B 111.0 . . ?
C4 C5 H5A 111.0 . . ?
C4 C5 H5B 111.0 . . ?
H5A C5 H5B 109.0 . . ?
N1 C6 H6A 109.4 . . ?
N1 C6 H6B 109.4 . . ?
N1 C6 C7 111.23(11) . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C6 C7 C8 111.58(11) . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
N2 C8 C7 108.48(11) . . ?
N2 C8 H8A 110.0 . . ?
N2 C8 H8B 110.0 . . ?
C7 C8 H8A 110.0 . . ?
C7 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
C1 O3 H3 108.6(14) . . ?
O1 C1 O3 118.46(12) . . ?
O2 C1 O1 125.20(12) . . ?
O2 C1 O3 116.34(12) . . ?

_olex2_date_sample_data_collection 2018-02-17
_olex2_date_sample_submission    2018-02-17
_olex2_submission_original_sample_id lw180217
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_p21n_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1866034'
_audit_update_record             
;
2018-09-05 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;
_audit_creation_date             2018-02-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        '[MTBDH][HCO3]'
_chemical_formula_moiety         'C H O3, C8 H16 N3'
_chemical_formula_sum            'C9 H17 N3 O3'
_chemical_formula_weight         215.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.14690(10)
_cell_length_b                   10.06590(10)
_cell_length_c                   12.9174(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.7990(10)
_cell_angle_gamma                90
_cell_volume                     1024.16(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5123
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.01
_cell_measurement_theta_min      2.60
_shelx_estimated_absorpt_T_max   1.000
_shelx_estimated_absorpt_T_min   0.994
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1012 before and 0.0400 after correction. The Ratio of minimum to maximum transmission is 0.9248. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.058
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14847
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.299
_diffrn_reflns_theta_min         2.599
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2207
_reflns_number_total             2537
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2537
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.038
_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)+(0.0448P)²+0.5472P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.0999
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C7(H7A,H7B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1D)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O2 O 0.66505(12) 0.75883(9) 0.39852(7) 0.0195(2) Uani 1 1 d . . . . .
O3 O 0.53804(13) 0.95635(9) 0.38522(7) 0.0229(2) Uani 1 1 d . . . . .
O1 O 0.59622(14) 0.84412(10) 0.53942(7) 0.0284(3) Uani 1 1 d . . . . .
H1D H 0.5493 0.9120 0.5565 0.043 Uiso 1 1 calc GR . . . .
N2 N 0.20225(13) 0.61488(10) 0.60581(8) 0.0145(2) Uani 1 1 d . . . . .
N1 N 0.23275(13) 0.46633(10) 0.47504(8) 0.0153(2) Uani 1 1 d . . . . .
H1 H 0.2511 0.4027 0.5233 0.018 Uiso 1 1 calc R . . . .
N3 N 0.17784(13) 0.68861(10) 0.43199(8) 0.0154(2) Uani 1 1 d . . . . .
C9 C 0.60016(14) 0.85310(11) 0.43672(9) 0.0136(2) Uani 1 1 d . . . . .
C2 C 0.20525(14) 0.58971(11) 0.50424(9) 0.0126(2) Uani 1 1 d . . . . .
C1 C 0.22493(15) 0.50866(12) 0.68478(9) 0.0158(2) Uani 1 1 d . . . . .
H1A H 0.1559 0.4319 0.6535 0.024 Uiso 1 1 calc GR . . . .
H1B H 0.1893 0.5398 0.7475 0.024 Uiso 1 1 calc GR . . . .
H1C H 0.3448 0.4828 0.7064 0.024 Uiso 1 1 calc GR . . . .
C8 C 0.20271(16) 0.75270(12) 0.64194(10) 0.0176(2) Uani 1 1 d . . . . .
H8A H 0.3172 0.7917 0.6516 0.021 Uiso 1 1 calc R . . . .
H8B H 0.1726 0.7562 0.7115 0.021 Uiso 1 1 calc R . . . .
C7 C 0.07416(17) 0.83033(12) 0.55834(10) 0.0203(3) Uani 1 1 d . . . . .
H7A H -0.0407 0.7928 0.5503 0.024 Uiso 1 1 calc R . . . .
H7B H 0.0728 0.9242 0.5809 0.024 Uiso 1 1 calc R . . . .
C3 C 0.23317(16) 0.43420(13) 0.36468(9) 0.0182(3) Uani 1 1 d . . . . .
H3A H 0.1157 0.4174 0.3218 0.022 Uiso 1 1 calc R . . . .
H3B H 0.3011 0.3530 0.3633 0.022 Uiso 1 1 calc R . . . .
C4 C 0.30855(16) 0.54948(13) 0.31777(10) 0.0200(3) Uani 1 1 d . . . . .
H4A H 0.4283 0.5627 0.3579 0.024 Uiso 1 1 calc R . . . .
H4B H 0.3056 0.5308 0.2421 0.024 Uiso 1 1 calc R . . . .
C5 C 0.20697(17) 0.67307(13) 0.32480(9) 0.0190(3) Uani 1 1 d . . . . .
H5A H 0.2685 0.7518 0.3082 0.023 Uiso 1 1 calc R . . . .
H5B H 0.0963 0.6681 0.2708 0.023 Uiso 1 1 calc R . . . .
C6 C 0.12217(17) 0.82231(12) 0.45292(10) 0.0198(3) Uani 1 1 d . . . . .
H6A H 0.0232 0.8480 0.3942 0.024 Uiso 1 1 calc R . . . .
H6B H 0.2147 0.8863 0.4537 0.024 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C9 1.2477(14) . ?
O3 C9 1.2676(14) . ?
O1 H1D 0.8400 . ?
O1 C9 1.3382(14) . ?
N2 C2 1.3426(15) . ?
N2 C1 1.4566(15) . ?
N2 C8 1.4634(15) . ?
N1 H1 0.8800 . ?
N1 C2 1.3334(15) . ?
N1 C3 1.4627(15) . ?
N3 C2 1.3437(15) . ?
N3 C5 1.4717(15) . ?
N3 C6 1.4672(15) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.5152(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C6 1.5119(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5104(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5096(18) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 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
C9 O1 H1D 109.5 . . ?
C2 N2 C1 121.01(10) . . ?
C2 N2 C8 119.43(10) . . ?
C1 N2 C8 118.88(9) . . ?
C2 N1 H1 119.2 . . ?
C2 N1 C3 121.60(10) . . ?
C3 N1 H1 119.2 . . ?
C2 N3 C5 122.45(10) . . ?
C2 N3 C6 123.77(10) . . ?
C6 N3 C5 113.74(10) . . ?
O2 C9 O3 124.65(11) . . ?
O2 C9 O1 117.42(10) . . ?
O3 C9 O1 117.92(10) . . ?
N2 C2 N3 119.85(10) . . ?
N1 C2 N2 119.90(10) . . ?
N1 C2 N3 120.25(10) . . ?
N2 C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
N2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C8 H8A 110.0 . . ?
N2 C8 H8B 110.0 . . ?
N2 C8 C7 108.46(10) . . ?
H8A C8 H8B 108.4 . . ?
C7 C8 H8A 110.0 . . ?
C7 C8 H8B 110.0 . . ?
C8 C7 H7A 109.9 . . ?
C8 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C6 C7 C8 108.89(10) . . ?
C6 C7 H7A 109.9 . . ?
C6 C7 H7B 109.9 . . ?
N1 C3 H3A 109.9 . . ?
N1 C3 H3B 109.9 . . ?
N1 C3 C4 108.88(10) . . ?
H3A C3 H3B 108.3 . . ?
C4 C3 H3A 109.9 . . ?
C4 C3 H3B 109.9 . . ?
C3 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
C5 C4 C3 108.89(10) . . ?
C5 C4 H4A 109.9 . . ?
C5 C4 H4B 109.9 . . ?
N3 C5 C4 111.52(10) . . ?
N3 C5 H5A 109.3 . . ?
N3 C5 H5B 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
N3 C6 C7 112.23(10) . . ?
N3 C6 H6A 109.2 . . ?
N3 C6 H6B 109.2 . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?

_olex2_date_sample_data_collection 2018-02-07
_olex2_date_sample_submission    2018-02-07
_olex2_submission_original_sample_id lw180207
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_p21n
_database_code_depnum_ccdc_archive 'CCDC 1866036'
_audit_update_record             
;
2018-09-05 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;
_audit_creation_date             2016-01-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4720)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H29 N3'
_chemical_formula_sum            'C23 H29 N3'
_chemical_formula_weight         347.49
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.5296(2)
_cell_length_b                   8.09390(10)
_cell_length_c                   19.7181(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.5378(12)
_cell_angle_gamma                90
_cell_volume                     1977.52(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5883
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.168
_cell_measurement_theta_min      3.006
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9054
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0808 before and 0.0390 after correction.
The Ratio of minimum to maximum transmission is 0.9054.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            22298
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.295
_diffrn_reflns_theta_min         3.519
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3833
_reflns_number_total             4895
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         4895
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.032
_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)+(0.0657P)²+1.0368P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1379
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H1A(0.6) H1B(0.4)
3.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C17(H17), C19(H19)
3.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C),
 C14(H14A,H14B,H14C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
N1 N -0.00388(12) 0.97251(17) 0.37111(7) 0.0235(3) Uani 1 1 d . . . . .
H1A H 0.039(2) 1.048(4) 0.3836(15) 0.016(7) Uiso 0.6 1 d . . P A 1
H1B H -0.076(4) 0.965(6) 0.360(2) 0.024(12) Uiso 0.4 1 d . . P B 2
N2 N 0.14797(9) 0.78832(14) 0.38548(6) 0.0145(2) Uani 1 1 d . . . . .
N3 N -0.01088(9) 0.68025(14) 0.35260(6) 0.0159(2) Uani 1 1 d . . . . .
C1 C 0.03985(11) 0.82901(17) 0.36996(7) 0.0151(3) Uani 1 1 d . . . . .
C2 C 0.16208(11) 0.61635(16) 0.38017(7) 0.0141(3) Uani 1 1 d . . . . .
C3 C 0.06435(11) 0.54988(17) 0.36028(7) 0.0156(3) Uani 1 1 d . . . . .
C4 C 0.27060(11) 0.54069(18) 0.39706(8) 0.0195(3) Uani 1 1 d . . . . .
H4A H 0.3191 0.5882 0.3676 0.029 Uiso 1 1 calc GR . . . .
H4B H 0.2652 0.4211 0.3896 0.029 Uiso 1 1 calc GR . . . .
H4C H 0.2992 0.5627 0.4452 0.029 Uiso 1 1 calc GR . . . .
C5 C 0.02925(12) 0.37571(18) 0.34751(9) 0.0233(3) Uani 1 1 d . . . . .
H5A H -0.0188 0.3438 0.3802 0.035 Uiso 1 1 calc GR . . . .
H5B H 0.0926 0.3033 0.3532 0.035 Uiso 1 1 calc GR . . . .
H5C H -0.0092 0.3652 0.3007 0.035 Uiso 1 1 calc GR . . . .
C6 C 0.23118(11) 0.90556(17) 0.40733(7) 0.0142(3) Uani 1 1 d . . . . .
C7 C 0.25460(11) 0.94546(18) 0.47690(7) 0.0181(3) Uani 1 1 d . . . . .
C8 C 0.33734(12) 1.05777(18) 0.49703(8) 0.0218(3) Uani 1 1 d . . . . .
H8 H 0.3545 1.0855 0.5442 0.026 Uiso 1 1 calc R . . . .
C9 C 0.39554(12) 1.13041(18) 0.45039(9) 0.0223(3) Uani 1 1 d . . . . .
C10 C 0.36992(12) 1.08786(19) 0.38138(8) 0.0216(3) Uani 1 1 d . . . . .
H10 H 0.4093 1.1369 0.3490 0.026 Uiso 1 1 calc R . . . .
C11 C 0.28841(11) 0.97576(18) 0.35873(7) 0.0177(3) Uani 1 1 d . . . . .
C12 C 0.19239(13) 0.8678(2) 0.52840(8) 0.0266(3) Uani 1 1 d . . . . .
H12A H 0.2066 0.7487 0.5307 0.040 Uiso 1 1 calc GR . . . .
H12B H 0.1150 0.8869 0.5144 0.040 Uiso 1 1 calc GR . . . .
H12C H 0.2151 0.9173 0.5736 0.040 Uiso 1 1 calc GR . . . .
C13 C 0.48357(13) 1.2545(2) 0.47363(10) 0.0311(4) Uani 1 1 d . . . . .
H13A H 0.5370 1.2526 0.4420 0.047 Uiso 1 1 calc GR . . . .
H13B H 0.5187 1.2261 0.5199 0.047 Uiso 1 1 calc GR . . . .
H13C H 0.4521 1.3653 0.4740 0.047 Uiso 1 1 calc GR . . . .
C14 C 0.26133(13) 0.9303(2) 0.28409(8) 0.0251(3) Uani 1 1 d . . . . .
H14A H 0.3076 0.9929 0.2574 0.038 Uiso 1 1 calc GR . . . .
H14B H 0.1855 0.9568 0.2678 0.038 Uiso 1 1 calc GR . . . .
H14C H 0.2732 0.8118 0.2785 0.038 Uiso 1 1 calc GR . . . .
C15 C -0.12568(11) 0.66052(17) 0.34164(7) 0.0162(3) Uani 1 1 d . . . . .
C16 C -0.17995(12) 0.64992(17) 0.39850(7) 0.0177(3) Uani 1 1 d . . . . .
C17 C -0.29082(12) 0.62588(19) 0.38727(8) 0.0201(3) Uani 1 1 d . . . . .
H17 H -0.3283 0.6160 0.4256 0.024 Uiso 1 1 calc R . . . .
C18 C -0.34869(12) 0.6159(2) 0.32124(8) 0.0229(3) Uani 1 1 d . . . . .
C19 C -0.29257(12) 0.6276(2) 0.26613(8) 0.0280(4) Uani 1 1 d . . . . .
H19 H -0.3311 0.6208 0.2209 0.034 Uiso 1 1 calc R . . . .
C20 C -0.18095(12) 0.6491(2) 0.27503(8) 0.0223(3) Uani 1 1 d . . . . .
C21 C -0.11950(13) 0.6651(2) 0.47019(8) 0.0254(3) Uani 1 1 d . . . . .
H21A H -0.0883 0.7760 0.4767 0.038 Uiso 1 1 calc GR . . . .
H21B H -0.0617 0.5826 0.4771 0.038 Uiso 1 1 calc GR . . . .
H21C H -0.1692 0.6466 0.5034 0.038 Uiso 1 1 calc GR . . . .
C22 C -0.46962(13) 0.5945(3) 0.31105(9) 0.0329(4) Uani 1 1 d . . . . .
H22A H -0.4888 0.5086 0.3421 0.049 Uiso 1 1 calc GR . . . .
H22B H -0.4949 0.5621 0.2635 0.049 Uiso 1 1 calc GR . . . .
H22C H -0.5037 0.6990 0.3209 0.049 Uiso 1 1 calc GR . . . .
C23 C -0.12233(14) 0.6581(3) 0.21368(9) 0.0353(4) Uani 1 1 d . . . . .
H23A H -0.1121 0.5462 0.1967 0.053 Uiso 1 1 calc GR . . . .
H23B H -0.0519 0.7106 0.2270 0.053 Uiso 1 1 calc GR . . . .
H23C H -0.1650 0.7232 0.1774 0.053 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.2858(19) . ?
N2 C1 1.3836(17) . ?
N2 C2 1.4090(17) . ?
N2 C6 1.4281(17) . ?
N3 C1 1.3807(18) . ?
N3 C3 1.4080(18) . ?
N3 C15 1.4314(17) . ?
C2 C3 1.3416(19) . ?
C2 C4 1.4833(19) . ?
C3 C5 1.487(2) . ?
C6 C7 1.397(2) . ?
C6 C11 1.3998(19) . ?
C7 C8 1.392(2) . ?
C7 C12 1.506(2) . ?
C8 C9 1.387(2) . ?
C9 C10 1.394(2) . ?
C9 C13 1.512(2) . ?
C10 C11 1.389(2) . ?
C11 C14 1.506(2) . ?
C15 C16 1.398(2) . ?
C15 C20 1.394(2) . ?
C16 C17 1.388(2) . ?
C16 C21 1.506(2) . ?
C17 C18 1.395(2) . ?
C18 C19 1.382(2) . ?
C18 C22 1.509(2) . ?
C19 C20 1.394(2) . ?
C20 C23 1.507(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N2 C2 110.38(11) . . ?
C1 N2 C6 123.75(11) . . ?
C2 N2 C6 125.79(11) . . ?
C1 N3 C3 110.53(11) . . ?
C1 N3 C15 123.37(12) . . ?
C3 N3 C15 125.06(12) . . ?
N1 C1 N2 128.09(13) . . ?
N1 C1 N3 127.62(13) . . ?
N3 C1 N2 104.29(11) . . ?
N2 C2 C4 120.80(12) . . ?
C3 C2 N2 107.38(12) . . ?
C3 C2 C4 131.80(13) . . ?
N3 C3 C5 121.05(12) . . ?
C2 C3 N3 107.36(12) . . ?
C2 C3 C5 131.59(13) . . ?
C7 C6 N2 119.16(12) . . ?
C7 C6 C11 121.60(13) . . ?
C11 C6 N2 119.24(12) . . ?
C6 C7 C12 120.74(13) . . ?
C8 C7 C6 118.04(13) . . ?
C8 C7 C12 121.22(14) . . ?
C9 C8 C7 122.05(14) . . ?
C8 C9 C10 118.37(14) . . ?
C8 C9 C13 120.83(15) . . ?
C10 C9 C13 120.80(15) . . ?
C11 C10 C9 121.79(14) . . ?
C6 C11 C14 120.39(13) . . ?
C10 C11 C6 118.15(14) . . ?
C10 C11 C14 121.45(13) . . ?
C16 C15 N3 118.90(12) . . ?
C20 C15 N3 119.82(13) . . ?
C20 C15 C16 121.27(13) . . ?
C15 C16 C21 120.74(13) . . ?
C17 C16 C15 118.38(13) . . ?
C17 C16 C21 120.88(13) . . ?
C16 C17 C18 121.76(13) . . ?
C17 C18 C22 120.23(14) . . ?
C19 C18 C17 118.36(13) . . ?
C19 C18 C22 121.41(14) . . ?
C18 C19 C20 121.83(14) . . ?
C15 C20 C19 118.39(14) . . ?
C15 C20 C23 121.33(13) . . ?
C19 C20 C23 120.28(14) . . ?

####################################################################### 
# 
# 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_p21c_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1866037'
_audit_update_record             
;
2018-09-05 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;
_audit_creation_date             2018-07-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H29 N3 O2'
_chemical_formula_sum            'C16 H29 N3 O2'
_chemical_formula_weight         295.42
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.3302(2)
_cell_length_b                   9.21940(10)
_cell_length_c                   12.9756(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.5879(6)
_cell_angle_gamma                90
_cell_volume                     1659.02(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9922
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.59
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9393
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1236 before and 0.0274 after correction.
The Ratio of minimum to maximum transmission is 0.9393.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27688
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.585
_diffrn_reflns_theta_min         2.653
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4346
_reflns_number_total             4642
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4642
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.057
_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)+(0.0514P)²+0.6113P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1027
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H5A(0.031) H5B(0.031) H5C(0.031) H6A(0.027) H6B(0.027) H6C(0.027)
 H11(0.017) H13A(0.03) H13B(0.03) H13C(0.03) H12A(0.036) H12B(0.036)
 H12C(0.036) H14(0.015) H15A(0.023) H15B(0.023) H15C(0.023) H16A(0.03)
 H16B(0.03) H16C(0.03) H8A(0.033) H8B(0.033) H8C(0.033) H10A(0.031) H10B(0.031)
 H10C(0.031) H9A(0.036) H9B(0.036) H9C(0.036)
 Fixed X: H5A(0.6949) H5B(0.6466) H5C(0.7614) H6A(0.5829) H6B(0.5631)
 H6C(0.5007) H11(0.8517) H13A(0.7517) H13B(0.8167) H13C(0.7155) H12A(0.9283)
 H12B(0.957) H12C(0.881) H14(0.6445) H15A(0.5186) H15B(0.4758) H15C(0.4692)
 H16A(0.5455) H16B(0.5874) H16C(0.6594) H8A(0.8889) H8B(0.7767) H8C(0.8203)
 H10A(0.8854) H10B(0.8151) H10C(0.928) H9A(0.9625) H9B(1) H9C(0.9347)
 Fixed Y: H5A(1.2494) H5B(1.1329) H5C(1.1393) H6A(0.77) H6B(0.931) H6C(0.8671)
 H11(1.1318) H13A(1.3493) H13B(1.3737) H13C(1.2913) H12A(1.0792) H12B(1.2333)
 H12C(1.2245) H14(0.7172) H15A(0.8835) H15B(0.7225) H15C(0.8269) H16A(0.616)
 H16B(0.5223) H16C(0.5921) H8A(0.6205) H8B(0.6304) H8C(0.7305) H10A(0.808)
 H10B(0.6777) H10C(0.6674) H9A(0.9583) H9B(0.8191) H9C(0.9378)
 Fixed Z: H5A(0.3323) H5B(0.2434) H5C(0.2872) H6A(0.2745) H6B(0.228)
 H6C(0.3039) H11(0.6198) H13A(0.4789) H13B(0.5974) H13C(0.5784) H12A(0.4791)
 H12B(0.5349) H12C(0.4211) H14(0.5962) H15A(0.5807) H15B(0.563) H15C(0.463)
 H16A(0.3916) H16B(0.4969) H16C(0.4342) H8A(0.7809) H8B(0.7215) H8C(0.823)
 H10A(0.538) H10B(0.55) H10C(0.6059) H9A(0.6941) H9B(0.7665) H9C(0.8052)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O1 O 0.65632(5) 1.05441(8) 0.68751(5) 0.01966(14) Uani 1 1 d . . . . .
O2 O 0.77330(5) 0.97457(9) 0.82683(5) 0.02355(16) Uani 1 1 d . . . . .
N1 N 0.77133(5) 0.90548(8) 0.65562(5) 0.01183(14) Uani 1 1 d . . . . .
N2 N 0.75261(5) 1.04942(7) 0.49494(5) 0.01157(14) Uani 1 1 d . . . . .
N3 N 0.65876(5) 0.86145(7) 0.48454(5) 0.01080(14) Uani 1 1 d . . . . .
C2 C 0.72958(6) 0.93714(8) 0.55031(6) 0.01065(15) Uani 1 1 d . . . . .
C3 C 0.69466(6) 1.04471(9) 0.39116(6) 0.01312(16) Uani 1 1 d . . . . .
C4 C 0.63646(6) 0.92644(9) 0.38456(6) 0.01263(15) Uani 1 1 d . . . . .
C5 C 0.69985(7) 1.15062(10) 0.30624(7) 0.02036(18) Uani 1 1 d . . . . .
H5A H 0.6949 1.2494 0.3323 0.031 Uiso 1 1 calc GR . . . .
H5B H 0.6466 1.1329 0.2434 0.031 Uiso 1 1 calc GR . . . .
H5C H 0.7614 1.1393 0.2872 0.031 Uiso 1 1 calc GR . . . .
C6 C 0.56465(6) 0.86869(10) 0.28959(7) 0.01805(17) Uani 1 1 d . . . . .
H6A H 0.5829 0.7700 0.2745 0.027 Uiso 1 1 calc GR . . . .
H6B H 0.5631 0.9310 0.2280 0.027 Uiso 1 1 calc GR . . . .
H6C H 0.5007 0.8671 0.3039 0.027 Uiso 1 1 calc GR . . . .
C11 C 0.82248(6) 1.16303(9) 0.54485(7) 0.01412(16) Uani 1 1 d . . . . .
H11 H 0.8517 1.1318 0.6198 0.017 Uiso 1 1 calc R . . . .
C13 C 0.77211(7) 1.30716(10) 0.55036(8) 0.01980(18) Uani 1 1 d . . . . .
H13A H 0.7517 1.3493 0.4789 0.030 Uiso 1 1 calc GR . . . .
H13B H 0.8167 1.3737 0.5974 0.030 Uiso 1 1 calc GR . . . .
H13C H 0.7155 1.2913 0.5784 0.030 Uiso 1 1 calc GR . . . .
C12 C 0.90452(7) 1.17620(11) 0.49010(9) 0.0237(2) Uani 1 1 d . . . . .
H12A H 0.9283 1.0792 0.4791 0.036 Uiso 1 1 calc GR . . . .
H12B H 0.9570 1.2333 0.5349 0.036 Uiso 1 1 calc GR . . . .
H12C H 0.8810 1.2245 0.4211 0.036 Uiso 1 1 calc GR . . . .
C14 C 0.60617(6) 0.74302(9) 0.52292(7) 0.01267(15) Uani 1 1 d . . . . .
H14 H 0.6445 0.7172 0.5962 0.015 Uiso 1 1 calc R . . . .
C15 C 0.50876(6) 0.79896(9) 0.53333(7) 0.01522(16) Uani 1 1 d . . . . .
H15A H 0.5186 0.8835 0.5807 0.023 Uiso 1 1 calc GR . . . .
H15B H 0.4758 0.7225 0.5630 0.023 Uiso 1 1 calc GR . . . .
H15C H 0.4692 0.8269 0.4630 0.023 Uiso 1 1 calc GR . . . .
C16 C 0.59898(7) 0.60613(10) 0.45539(8) 0.02022(18) Uani 1 1 d . . . . .
H16A H 0.5455 0.6160 0.3916 0.030 Uiso 1 1 calc GR . . . .
H16B H 0.5874 0.5223 0.4969 0.030 Uiso 1 1 calc GR . . . .
H16C H 0.6594 0.5921 0.4342 0.030 Uiso 1 1 calc GR . . . .
C7 C 0.85539(6) 0.80416(9) 0.68633(7) 0.01451(16) Uani 1 1 d . . . . .
C8 C 0.83332(7) 0.68573(11) 0.75954(8) 0.02183(19) Uani 1 1 d . . . . .
H8A H 0.8889 0.6205 0.7809 0.033 Uiso 1 1 calc GR . . . .
H8B H 0.7767 0.6304 0.7215 0.033 Uiso 1 1 calc GR . . . .
H8C H 0.8203 0.7305 0.8230 0.033 Uiso 1 1 calc GR . . . .
C10 C 0.87250(7) 0.73288(11) 0.58603(8) 0.02064(18) Uani 1 1 d . . . . .
H10A H 0.8854 0.8080 0.5380 0.031 Uiso 1 1 calc GR . . . .
H10B H 0.8151 0.6777 0.5500 0.031 Uiso 1 1 calc GR . . . .
H10C H 0.9280 0.6674 0.6059 0.031 Uiso 1 1 calc GR . . . .
C9 C 0.94634(7) 0.88732(12) 0.74316(8) 0.0237(2) Uani 1 1 d . . . . .
H9A H 0.9625 0.9583 0.6941 0.036 Uiso 1 1 calc GR . . . .
H9B H 1.0000 0.8191 0.7665 0.036 Uiso 1 1 calc GR . . . .
H9C H 0.9347 0.9378 0.8052 0.036 Uiso 1 1 calc GR . . . .
C1 C 0.73041(6) 0.98506(9) 0.73151(7) 0.01491(16) 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
O1 C1 1.2476(11) . ?
O2 C1 1.2385(11) . ?
N1 C2 1.3779(10) . ?
N1 C7 1.4969(10) . ?
N1 C1 1.4637(10) . ?
N2 C2 1.3475(10) . ?
N2 C3 1.3935(10) . ?
N2 C11 1.4807(10) . ?
N3 C2 1.3450(10) . ?
N3 C4 1.3912(10) . ?
N3 C14 1.4823(10) . ?
C3 C4 1.3623(12) . ?
C3 C5 1.4880(12) . ?
C4 C6 1.4907(12) . ?
C11 C13 1.5224(12) . ?
C11 C12 1.5240(12) . ?
C14 C15 1.5256(11) . ?
C14 C16 1.5250(12) . ?
C7 C8 1.5316(12) . ?
C7 C10 1.5319(13) . ?
C7 C9 1.5317(13) . ?

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 C7 121.03(7) . . ?
C2 N1 C1 114.43(7) . . ?
C1 N1 C7 124.44(7) . . ?
C2 N2 C3 108.96(7) . . ?
C2 N2 C11 122.66(7) . . ?
C3 N2 C11 128.13(7) . . ?
C2 N3 C4 109.12(7) . . ?
C2 N3 C14 122.36(7) . . ?
C4 N3 C14 127.87(7) . . ?
N2 C2 N1 126.01(7) . . ?
N3 C2 N1 126.09(7) . . ?
N3 C2 N2 107.90(7) . . ?
N2 C3 C5 124.50(8) . . ?
C4 C3 N2 106.98(7) . . ?
C4 C3 C5 128.51(8) . . ?
N3 C4 C6 124.44(8) . . ?
C3 C4 N3 107.04(7) . . ?
C3 C4 C6 128.47(8) . . ?
N2 C11 C13 111.20(7) . . ?
N2 C11 C12 111.62(7) . . ?
C13 C11 C12 112.51(8) . . ?
N3 C14 C15 109.55(7) . . ?
N3 C14 C16 112.52(7) . . ?
C16 C14 C15 113.56(7) . . ?
N1 C7 C8 109.39(7) . . ?
N1 C7 C10 109.38(7) . . ?
N1 C7 C9 110.24(7) . . ?
C8 C7 C10 108.86(8) . . ?
C8 C7 C9 109.99(7) . . ?
C9 C7 C10 108.96(7) . . ?
O1 C1 N1 112.83(7) . . ?
O2 C1 O1 130.39(8) . . ?
O2 C1 N1 116.78(8) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_c2c
_database_code_depnum_ccdc_archive 'CCDC 1866039'
_audit_update_record             
;
2018-09-05 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;
_audit_creation_date             2018-07-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H23 N3 O2'
_chemical_formula_sum            'C13 H23 N3 O2'
_chemical_formula_weight         253.34
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   10.37650(10)
_cell_length_b                   13.1188(2)
_cell_length_c                   11.2806(2)
_cell_angle_alpha                90
_cell_angle_beta                 114.6046(6)
_cell_angle_gamma                90
_cell_volume                     1396.16(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6238
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.55
_cell_measurement_theta_min      2.659
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9350
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1005 before and 0.0292 after correction.
The Ratio of minimum to maximum transmission is 0.9350.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0151
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9420
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.555
_diffrn_reflns_theta_min         2.659
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.942
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.943
_reflns_number_gt                3728
_reflns_number_total             3803
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1768 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         3803
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0420
_refine_ls_restrained_S_all      1.059
_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)+(0.0655P)²+0.7830P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1135
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H5A(0.036) H5B(0.036) H5C(0.036) H6A(0.041) H6B(0.041) H6C(0.041)
 H8(0.02) H10A(0.036) H10B(0.036) H10C(0.036) H9A(0.036) H9B(0.036) H9C(0.036)
 H11(0.025) H12A(0.039) H12B(0.039) H12C(0.039) H13A(0.054) H13B(0.054)
 H13C(0.054) H7A(0.039) H7B(0.039) H7C(0.039)
 Fixed X: H5A(-0.36) H5B(-0.2637) H5C(-0.3956) H6A(-0.0159) H6B(-0.0471)
 H6C(0.0886) H8(-0.3753) H10A(-0.5195) H10B(-0.6003) H10C(-0.5444) H9A(-0.3927)
 H9B(-0.4423) H9C(-0.2773) H11(0.0589) H12A(0.189) H12B(0.2824) H12C(0.2279)
 H13A(0.1) H13B(0.1453) H13C(-0.0188) H7A(-0.2106) H7B(-0.3107) H7C(-0.1559)
 Fixed Y: H5A(-0.6381) H5B(-0.7158) H5C(-0.6608) H6A(-0.674) H6B(-0.7215) H6C(-
 0.6504) H8(-0.3413) H10A(-0.444) H10B(-0.4051) H10C(-0.5201) H9A(-0.506) H9B(-
 0.3911) H9C(-0.4169) H11(-0.3541) H12A(-0.4286) H12B(-0.4092) H12C(-0.5217)
 H13A(-0.5381) H13B(-0.4263) H13C(-0.4561) H7A(-0.1801) H7B(-0.2767) H7C(-
 0.2729)
 Fixed Z: H5A(-0.5107) H5B(-0.5478) H5C(-0.6605) H6A(-0.6646) H6B(-0.5485)
 H6C(-0.5163) H8(-0.5742) H10A(-0.7566) H10B(-0.6714) H10C(-0.6572) H9A(-
 0.4169) H9B(-0.4125) H9C(-0.3631) H11(-0.6078) H12A(-0.402) H12B(-0.4825)
 H12C(-0.4729) H13A(-0.7179) H13B(-0.7426) H13C(-0.7972) H7A(-0.7085) H7B(-
 0.7691) H7C(-0.7674)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O1 O -0.05673(19) -0.30383(13) -0.37330(16) 0.0300(4) Uani 1 1 d . . . . .
O2 O -0.0920(2) -0.15402(12) -0.4817(2) 0.0340(4) Uani 1 1 d . . . . .
N1 N -0.1544(2) -0.30330(11) -0.59241(17) 0.0202(3) Uani 1 1 d . . . . .
N2 N -0.26199(16) -0.46431(12) -0.57896(15) 0.0144(3) Uani 1 1 d . . . . .
N3 N -0.05665(17) -0.47113(13) -0.58760(15) 0.0174(3) Uani 1 1 d . . . . .
C2 C -0.1578(2) -0.40794(13) -0.58617(19) 0.0161(3) Uani 1 1 d . . . . .
C3 C -0.2255(2) -0.56691(14) -0.57370(18) 0.0160(3) Uani 1 1 d . . . . .
C4 C -0.0962(2) -0.57080(15) -0.57863(18) 0.0193(4) Uani 1 1 d . . . . .
C5 C -0.3192(2) -0.65271(15) -0.5732(2) 0.0242(4) Uani 1 1 d . . . . .
H5A H -0.3600 -0.6381 -0.5107 0.036 Uiso 1 1 calc GR . . . .
H5B H -0.2637 -0.7158 -0.5478 0.036 Uiso 1 1 calc GR . . . .
H5C H -0.3956 -0.6608 -0.6605 0.036 Uiso 1 1 calc GR . . . .
C6 C -0.0104(3) -0.66193(18) -0.5768(2) 0.0272(5) Uani 1 1 d . . . . .
H6A H -0.0159 -0.6740 -0.6646 0.041 Uiso 1 1 calc GR . . . .
H6B H -0.0471 -0.7215 -0.5485 0.041 Uiso 1 1 calc GR . . . .
H6C H 0.0886 -0.6504 -0.5163 0.041 Uiso 1 1 calc GR . . . .
C8 C -0.38360(19) -0.41643(15) -0.56441(18) 0.0169(4) Uani 1 1 d . . . . .
H8 H -0.3753 -0.3413 -0.5742 0.020 Uiso 1 1 calc R . . . .
C10 C -0.5245(2) -0.44934(18) -0.6720(2) 0.0242(4) Uani 1 1 d . . . . .
H10A H -0.5195 -0.4440 -0.7566 0.036 Uiso 1 1 calc GR . . . .
H10B H -0.6003 -0.4051 -0.6714 0.036 Uiso 1 1 calc GR . . . .
H10C H -0.5444 -0.5201 -0.6572 0.036 Uiso 1 1 calc GR . . . .
C9 C -0.3730(2) -0.43418(18) -0.4269(2) 0.0239(4) Uani 1 1 d . . . . .
H9A H -0.3927 -0.5060 -0.4169 0.036 Uiso 1 1 calc GR . . . .
H9B H -0.4423 -0.3911 -0.4125 0.036 Uiso 1 1 calc GR . . . .
H9C H -0.2773 -0.4169 -0.3631 0.036 Uiso 1 1 calc GR . . . .
C11 C 0.0713(2) -0.42973(16) -0.6000(2) 0.0210(4) Uani 1 1 d . . . . .
H11 H 0.0589 -0.3541 -0.6078 0.025 Uiso 1 1 calc R . . . .
C12 C 0.2043(2) -0.4490(2) -0.4788(2) 0.0261(4) Uani 1 1 d . . . . .
H12A H 0.1890 -0.4286 -0.4020 0.039 Uiso 1 1 calc GR . . . .
H12B H 0.2824 -0.4092 -0.4825 0.039 Uiso 1 1 calc GR . . . .
H12C H 0.2279 -0.5217 -0.4729 0.039 Uiso 1 1 calc GR . . . .
C13 C 0.0748(3) -0.4657(2) -0.7254(2) 0.0362(6) Uani 1 1 d . . . . .
H13A H 0.1000 -0.5381 -0.7179 0.054 Uiso 1 1 calc GR . . . .
H13B H 0.1453 -0.4263 -0.7426 0.054 Uiso 1 1 calc GR . . . .
H13C H -0.0188 -0.4561 -0.7972 0.054 Uiso 1 1 calc GR . . . .
C7 C -0.2127(2) -0.25421(17) -0.7198(2) 0.0257(4) Uani 1 1 d . . . . .
H7A H -0.2106 -0.1801 -0.7085 0.039 Uiso 1 1 calc GR . . . .
H7B H -0.3107 -0.2767 -0.7691 0.039 Uiso 1 1 calc GR . . . .
H7C H -0.1559 -0.2729 -0.7674 0.039 Uiso 1 1 calc GR . . . .
C1 C -0.0958(2) -0.24781(16) -0.4710(2) 0.0222(4) 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
O1 C1 1.244(3) . ?
O2 C1 1.239(3) . ?
N1 C2 1.376(2) . ?
N1 C7 1.456(3) . ?
N1 C1 1.443(3) . ?
N2 C2 1.340(3) . ?
N2 C3 1.393(2) . ?
N2 C8 1.479(2) . ?
N3 C2 1.343(3) . ?
N3 C4 1.387(3) . ?
N3 C11 1.495(3) . ?
C3 C4 1.366(2) . ?
C3 C5 1.490(3) . ?
C4 C6 1.486(3) . ?
C8 C10 1.523(3) . ?
C8 C9 1.526(3) . ?
C11 C12 1.505(3) . ?
C11 C13 1.505(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C7 118.87(17) . . ?
C2 N1 C1 117.67(17) . . ?
C1 N1 C7 123.45(16) . . ?
C2 N2 C3 108.88(16) . . ?
C2 N2 C8 121.32(16) . . ?
C3 N2 C8 129.46(16) . . ?
C2 N3 C4 108.96(16) . . ?
C2 N3 C11 120.40(17) . . ?
C4 N3 C11 130.63(17) . . ?
N2 C2 N1 126.3(2) . . ?
N2 C2 N3 108.32(15) . . ?
N3 C2 N1 125.4(2) . . ?
N2 C3 C5 124.31(18) . . ?
C4 C3 N2 106.78(17) . . ?
C4 C3 C5 128.8(2) . . ?
N3 C4 C6 124.4(2) . . ?
C3 C4 N3 107.05(18) . . ?
C3 C4 C6 128.5(2) . . ?
N2 C8 C10 111.82(16) . . ?
N2 C8 C9 110.14(15) . . ?
C10 C8 C9 113.92(17) . . ?
N3 C11 C12 111.57(17) . . ?
N3 C11 C13 110.10(17) . . ?
C13 C11 C12 115.5(2) . . ?
O1 C1 N1 113.33(17) . . ?
O2 C1 O1 131.4(2) . . ?
O2 C1 N1 115.25(19) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound3bHBF4
_database_code_depnum_ccdc_archive 'CCDC 1880247'
_audit_update_record             
;
2018-11-21 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;
_audit_creation_date             2018-11-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'B F4, C15 H30 N3'
_chemical_formula_sum            'C15 H30 B F4 N3'
_chemical_formula_weight         339.23
_chemical_melting_point          ?
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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.2506(3)
_cell_length_b                   10.8267(2)
_cell_length_c                   10.8569(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.0900(10)
_cell_angle_gamma                90
_cell_volume                     1792.62(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9972
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1364 before and 0.0600 after correction. The Ratio of minimum to maximum transmission is 0.9256. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.213
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.097
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24044
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         1.876
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3442
_reflns_number_total             3656
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2007)'
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3656
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.085
_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)+(0.0409P)²+1.0861P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1065
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.8978(9)
 0.1022(9)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C), C6(H6A,H6B,H6C), C15(H15A,H15B,H15C),
 C5(H5A,H5B,H5C), C13(H13A,H13B,H13C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C),
  C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
F4 F 0.71241(8) 0.29513(10) 0.19047(10) 0.0325(3) Uani 1 1 d . . . . .
F3 F 0.67051(8) 0.49252(11) 0.22514(12) 0.0350(3) Uani 1 1 d . . . . .
F1 F 0.81330(7) 0.44207(12) 0.23184(13) 0.0409(3) Uani 1 1 d . . . . .
F2 F 0.72175(12) 0.37567(12) 0.38258(11) 0.0525(4) Uani 1 1 d . . . . .
N2 N 0.81882(9) 0.44483(12) 0.80934(12) 0.0152(3) Uani 1 1 d . . . . .
N3 N 0.67615(9) 0.46505(12) 0.80673(12) 0.0152(3) Uani 1 1 d . . . . .
N1 N 0.75477(9) 0.50817(13) 0.61534(12) 0.0155(3) Uani 1 1 d . . . . .
C1 C 0.74911(10) 0.47210(14) 0.73563(14) 0.0133(3) Uani 1 1 d . . . . .
C2 C 0.70158(12) 0.44178(17) 0.92598(15) 0.0210(4) Uani 1 1 d . . . . .
H2 H 0.6637 0.4354 0.9951 0.025 Uiso 1 1 calc R . . . .
C3 C 0.78865(12) 0.42978(17) 0.92790(15) 0.0212(4) Uani 1 1 d . . . . .
H3 H 0.8237 0.4137 0.9986 0.025 Uiso 1 1 calc R . . . .
C12 C 0.58003(10) 0.46944(16) 0.77077(16) 0.0181(3) Uani 1 1 d . . . . .
C7 C 0.84478(12) 0.64793(17) 0.48925(16) 0.0214(4) Uani 1 1 d . . . . .
H7A H 0.8976 0.6253 0.5356 0.032 Uiso 1 1 calc GR . . . .
H7B H 0.8506 0.7327 0.4586 0.032 Uiso 1 1 calc GR . . . .
H7C H 0.8374 0.5913 0.4196 0.032 Uiso 1 1 calc GR . . . .
C8 C 0.91287(10) 0.41725(16) 0.77440(16) 0.0179(3) Uani 1 1 d . . . . .
C4 C 0.76451(11) 0.63926(15) 0.57384(14) 0.0174(3) Uani 1 1 d . . . . .
C14 C 0.56586(12) 0.42415(18) 0.63899(17) 0.0235(4) Uani 1 1 d . . . . .
H14A H 0.5904 0.4844 0.5811 0.035 Uiso 1 1 calc GR . . . .
H14B H 0.5029 0.4146 0.6233 0.035 Uiso 1 1 calc GR . . . .
H14C H 0.5952 0.3444 0.6280 0.035 Uiso 1 1 calc GR . . . .
C6 C 0.77522(12) 0.72462(16) 0.68475(16) 0.0221(4) Uani 1 1 d . . . . .
H6A H 0.7235 0.7179 0.7378 0.033 Uiso 1 1 calc GR . . . .
H6B H 0.7814 0.8101 0.6563 0.033 Uiso 1 1 calc GR . . . .
H6C H 0.8276 0.7007 0.7314 0.033 Uiso 1 1 calc GR . . . .
C15 C 0.53105(12) 0.38148(17) 0.85691(18) 0.0249(4) Uani 1 1 d . . . . .
H15A H 0.5580 0.2994 0.8532 0.037 Uiso 1 1 calc GR . . . .
H15B H 0.4695 0.3758 0.8313 0.037 Uiso 1 1 calc GR . . . .
H15C H 0.5342 0.4129 0.9415 0.037 Uiso 1 1 calc GR . . . .
C5 C 0.68423(12) 0.67937(17) 0.49875(16) 0.0225(4) Uani 1 1 d . . . . .
H5A H 0.6751 0.6215 0.4305 0.034 Uiso 1 1 calc GR . . . .
H5B H 0.6939 0.7625 0.4659 0.034 Uiso 1 1 calc GR . . . .
H5C H 0.6323 0.6797 0.5519 0.034 Uiso 1 1 calc GR . . . .
C13 C 0.54675(12) 0.60098(17) 0.78939(18) 0.0243(4) Uani 1 1 d . . . . .
H13A H 0.5567 0.6260 0.8750 0.036 Uiso 1 1 calc GR . . . .
H13B H 0.4839 0.6043 0.7709 0.036 Uiso 1 1 calc GR . . . .
H13C H 0.5783 0.6571 0.7342 0.036 Uiso 1 1 calc GR . . . .
C10 C 0.91707(12) 0.35560(17) 0.64773(16) 0.0229(4) Uani 1 1 d . . . . .
H10A H 0.8764 0.2855 0.6454 0.034 Uiso 1 1 calc GR . . . .
H10B H 0.9769 0.3263 0.6325 0.034 Uiso 1 1 calc GR . . . .
H10C H 0.9006 0.4155 0.5841 0.034 Uiso 1 1 calc GR . . . .
C11 C 0.94965(13) 0.32578(19) 0.86860(19) 0.0291(4) Uani 1 1 d . . . . .
H11A H 0.9512 0.3647 0.9501 0.044 Uiso 1 1 calc GR . . . .
H11B H 1.0092 0.3017 0.8446 0.044 Uiso 1 1 calc GR . . . .
H11C H 0.9122 0.2523 0.8715 0.044 Uiso 1 1 calc GR . . . .
C9 C 0.96647(12) 0.53609(18) 0.77963(19) 0.0266(4) Uani 1 1 d . . . . .
H9A H 0.9456 0.5933 0.7161 0.040 Uiso 1 1 calc GR . . . .
H9B H 1.0284 0.5170 0.7652 0.040 Uiso 1 1 calc GR . . . .
H9C H 0.9599 0.5743 0.8609 0.040 Uiso 1 1 calc GR . . . .
B1 B 0.72956(13) 0.40101(18) 0.25829(18) 0.0204(4) Uani 1 1 d . . . . .
H1 H 0.7379(14) 0.459(2) 0.563(2) 0.023(5) 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
F4 B1 1.387(2) . ?
F3 B1 1.386(2) . ?
F1 B1 1.383(2) . ?
F2 B1 1.382(2) . ?
N2 C1 1.362(2) . ?
N2 C3 1.377(2) . ?
N2 C8 1.514(2) . ?
N3 C1 1.357(2) . ?
N3 C2 1.374(2) . ?
N3 C12 1.517(2) . ?
N1 C1 1.366(2) . ?
N1 C4 1.497(2) . ?
N1 H1 0.82(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.334(3) . ?
C3 H3 0.9500 . ?
C12 C14 1.527(2) . ?
C12 C15 1.530(2) . ?
C12 C13 1.525(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 C4 1.534(2) . ?
C8 C10 1.530(2) . ?
C8 C11 1.530(2) . ?
C8 C9 1.525(2) . ?
C4 C6 1.526(2) . ?
C4 C5 1.533(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
C1 N2 C3 108.26(14) . . ?
C1 N2 C8 129.38(13) . . ?
C3 N2 C8 121.92(14) . . ?
C1 N3 C2 108.40(13) . . ?
C1 N3 C12 130.12(13) . . ?
C2 N3 C12 121.29(14) . . ?
C1 N1 C4 124.43(13) . . ?
C1 N1 H1 116.7(15) . . ?
C4 N1 H1 116.5(15) . . ?
N2 C1 N1 124.98(15) . . ?
N3 C1 N2 107.06(13) . . ?
N3 C1 N1 127.80(14) . . ?
N3 C2 H2 125.9 . . ?
C3 C2 N3 108.18(15) . . ?
C3 C2 H2 125.9 . . ?
N2 C3 H3 126.0 . . ?
C2 C3 N2 107.92(15) . . ?
C2 C3 H3 126.0 . . ?
N3 C12 C14 111.49(13) . . ?
N3 C12 C15 107.20(14) . . ?
N3 C12 C13 108.46(13) . . ?
C14 C12 C15 107.71(14) . . ?
C13 C12 C14 112.16(15) . . ?
C13 C12 C15 109.70(14) . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
N2 C8 C10 110.63(13) . . ?
N2 C8 C11 107.87(14) . . ?
N2 C8 C9 109.40(13) . . ?
C11 C8 C10 107.62(14) . . ?
C9 C8 C10 112.22(15) . . ?
C9 C8 C11 108.98(15) . . ?
N1 C4 C7 108.53(13) . . ?
N1 C4 C6 110.32(13) . . ?
N1 C4 C5 110.44(14) . . ?
C6 C4 C7 110.53(14) . . ?
C6 C4 C5 109.42(14) . . ?
C5 C4 C7 107.56(13) . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
F3 B1 F4 109.33(15) . . ?
F1 B1 F4 109.20(16) . . ?
F1 B1 F3 108.43(15) . . ?
F2 B1 F4 109.74(15) . . ?
F2 B1 F3 109.78(16) . . ?
F2 B1 F1 110.33(16) . . ?

_olex2_date_sample_data_collection 2018-07-13
_olex2_date_sample_submission    2018-07-13
_olex2_submission_original_sample_id lw180713
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.8978(9)
2 0.1022(9)

####################################################################### 
# 
# 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_p21c_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1866035'
_audit_update_record             
;
2018-09-05 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;
_audit_creation_date             2018-07-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C8 H13 N3 O2'
_chemical_formula_sum            'C8 H13 N3 O2'
_chemical_formula_weight         183.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.6679(3)
_cell_length_b                   14.6889(5)
_cell_length_c                   9.6025(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.1304(18)
_cell_angle_gamma                90
_cell_volume                     912.05(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.507
_cell_measurement_theta_min      3.442
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0709 before and 0.0385 after correction.
The Ratio of minimum to maximum transmission is 0.9156.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20261
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.514
_diffrn_reflns_theta_min         3.533
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2583
_reflns_number_total             2785
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         2785
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.052
_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)+(0.0589P)²+0.3913P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1110
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H5A(0.021) H5B(0.021) H5C(0.021) H6A(0.027) H6B(0.027) H6C(0.027)
 H7A(0.027) H7B(0.027) H7C(0.027) H8A(0.029) H8B(0.029) H8C(0.029)
 Fixed X: H5A(0.5068) H5B(0.557) H5C(0.4444) H6A(0.1304) H6B(-0.0418)
 H6C(0.1981) H7A(-0.2911) H7B(-0.3027) H7C(-0.3793) H8A(-0.1728) H8B(-0.0065)
 H8C(-0.2052)
 Fixed Y: H5A(0.4742) H5B(0.369) H5C(0.3995) H6A(0.5211) H6B(0.5692)
 H6C(0.5825) H7A(0.4728) H7B(0.5148) H7C(0.4128) H8A(0.2396) H8B(0.2567)
 H8C(0.3211)
 Fixed Z: H5A(0.3526) H5B(0.3339) H5C(0.4558) H6A(0.4382) H6B(0.3146)
 H6C(0.3197) H7A(-0.0319) H7B(0.1197) H7C(0.079) H8A(0.0169) H8B(-0.0756) H8C(-
 0.0969)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O1 O 0.32050(12) 0.20245(5) 0.35557(7) 0.01803(16) Uani 1 1 d . . . . .
O2 O 0.47455(12) 0.12569(5) 0.20725(8) 0.01992(17) Uani 1 1 d . . . . .
N1 N 0.33522(13) 0.26417(5) 0.14133(8) 0.01378(16) Uani 1 1 d . . . . .
H1 H 0.350(2) 0.2580(11) 0.0578(17) 0.024(4) Uiso 1 1 d . . . . .
N2 N 0.25680(12) 0.40062(5) 0.25690(8) 0.01189(16) Uani 1 1 d . . . . .
N3 N 0.01215(12) 0.34710(5) 0.08442(8) 0.01331(16) Uani 1 1 d . . . . .
C1 C 0.38035(13) 0.19122(6) 0.24307(9) 0.01210(17) Uani 1 1 d . . . . .
C2 C 0.20773(14) 0.33365(6) 0.16003(9) 0.01207(17) Uani 1 1 d . . . . .
C3 C 0.08729(14) 0.45812(6) 0.24435(10) 0.01322(17) Uani 1 1 d . . . . .
C4 C -0.06595(14) 0.42509(6) 0.13499(10) 0.01388(18) Uani 1 1 d . . . . .
C5 C 0.45776(14) 0.41175(6) 0.35812(10) 0.01417(17) Uani 1 1 d . . . . .
H5A H 0.5068 0.4742 0.3526 0.021 Uiso 1 1 calc GR . . . .
H5B H 0.5570 0.3690 0.3339 0.021 Uiso 1 1 calc GR . . . .
H5C H 0.4444 0.3995 0.4558 0.021 Uiso 1 1 calc GR . . . .
C6 C 0.09405(15) 0.53970(6) 0.33713(11) 0.01787(19) Uani 1 1 d . . . . .
H6A H 0.1304 0.5211 0.4382 0.027 Uiso 1 1 calc GR . . . .
H6B H -0.0418 0.5692 0.3146 0.027 Uiso 1 1 calc GR . . . .
H6C H 0.1981 0.5825 0.3197 0.027 Uiso 1 1 calc GR . . . .
C7 C -0.27778(15) 0.45930(7) 0.06994(11) 0.01807(19) Uani 1 1 d . . . . .
H7A H -0.2911 0.4728 -0.0319 0.027 Uiso 1 1 calc GR . . . .
H7B H -0.3027 0.5148 0.1197 0.027 Uiso 1 1 calc GR . . . .
H7C H -0.3793 0.4128 0.0790 0.027 Uiso 1 1 calc GR . . . .
C8 C -0.10252(16) 0.28610(7) -0.02695(11) 0.0195(2) Uani 1 1 d . . . . .
H8A H -0.1728 0.2396 0.0169 0.029 Uiso 1 1 calc GR . . . .
H8B H -0.0065 0.2567 -0.0756 0.029 Uiso 1 1 calc GR . . . .
H8C H -0.2052 0.3211 -0.0969 0.029 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2506(11) . ?
O2 C1 1.2430(11) . ?
N1 C1 1.4317(11) . ?
N1 C2 1.3679(11) . ?
N2 C2 1.3384(11) . ?
N2 C3 1.3925(11) . ?
N2 C5 1.4598(11) . ?
N3 C2 1.3433(11) . ?
N3 C4 1.3939(12) . ?
N3 C8 1.4602(12) . ?
C3 C4 1.3632(13) . ?
C3 C6 1.4872(13) . ?
C4 C7 1.4856(13) . ?

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 C1 120.18(8) . . ?
C2 N2 C3 109.28(7) . . ?
C2 N2 C5 125.03(8) . . ?
C3 N2 C5 125.69(7) . . ?
C2 N3 C4 109.18(7) . . ?
C2 N3 C8 124.84(8) . . ?
C4 N3 C8 125.88(8) . . ?
O1 C1 N1 115.63(8) . . ?
O2 C1 O1 129.09(9) . . ?
O2 C1 N1 115.28(8) . . ?
N2 C2 N1 125.82(8) . . ?
N2 C2 N3 107.93(8) . . ?
N3 C2 N1 126.24(8) . . ?
N2 C3 C6 122.11(8) . . ?
C4 C3 N2 106.90(8) . . ?
C4 C3 C6 130.97(9) . . ?
N3 C4 C7 121.95(8) . . ?
C3 C4 N3 106.70(8) . . ?
C3 C4 C7 131.33(9) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_p2c_a
_database_code_depnum_ccdc_archive 'CCDC 1866038'
_audit_update_record             
;
2018-09-05 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;
_audit_creation_date             2018-07-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H27 N3 O2, 0.75(C6 H6)'
_chemical_formula_sum            'C19.50 H31.50 N3 O2'
_chemical_formula_weight         339.98
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.6071(2)
_cell_length_b                   41.9109(7)
_cell_length_c                   14.5422(2)
_cell_angle_alpha                90
_cell_angle_beta                 117.1590(10)
_cell_angle_gamma                90
_cell_volume                     7921.1(2)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9810
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.50
_shelx_estimated_absorpt_T_max   0.962
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1642 before and 0.0458 after correction. The Ratio of minimum to maximum transmission is 0.7945. The λ/2 correction factor is Not present.'
_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             2968
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.548
_exptl_crystal_size_min          0.521
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       52
_diffrn_reflns_limit_k_min       -52
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            107880
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.386
_diffrn_reflns_theta_min         1.567
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                13986
_reflns_number_total             16183
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2007)'
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     931
_refine_ls_number_reflns         16183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.057
_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)+(0.0449P)²+5.5312P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1241
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H33(0.028) H34(0.029) H35A(0.046) H35B(0.046) H35C(0.046)
 H35D(0.046) H36A(0.03) H36B(0.03) H36C(0.029) H36D(0.029) H37A(0.043)
 H37B(0.043) H37C(0.043) H37D(0.048) H37E(0.048) H37F(0.048) H39A(0.056)
 H39B(0.056) H39C(0.056) H40A(0.051) H40B(0.051) H40C(0.051) H41A(0.041)
 H41B(0.041) H41C(0.041) H43A(0.055) H43B(0.055) H43C(0.055) H44A(0.048)
 H44B(0.048) H44C(0.048) H45A(0.076) H45B(0.076) H45C(0.076) H18(0.032)
 H19(0.036) H20A(0.045) H20B(0.045) H21A(0.051) H21B(0.051) H22A(0.09)
 H22B(0.09) H22C(0.09) H24A(0.084) H24B(0.084) H24C(0.084) H25A(0.086)
 H25B(0.086) H25C(0.086) H26A(0.059) H26B(0.059) H26C(0.059) H28A(0.082)
 H28B(0.082) H28C(0.082) H29A(0.081) H29B(0.081) H29C(0.081) H30A(0.074)
 H30B(0.074) H30C(0.074) H48(0.023) H49(0.022) H50A(0.024) H50B(0.024)
 H51A(0.028) H51B(0.028) H52A(0.044) H52B(0.044) H52C(0.044) H54A(0.076)
 H54B(0.076) H54C(0.076) H55A(0.051) H55B(0.051) H55C(0.051) H56A(0.06)
 H56B(0.06) H56C(0.06) H58A(0.048) H58B(0.048) H58C(0.048) H59A(0.042)
 H59B(0.042) H59C(0.042) H60A(0.042) H60B(0.042) H60C(0.042) H3(0.032)
 H4(0.033) H5A(0.031) H5B(0.031) H6A(0.036) H6B(0.036) H7A(0.062) H7B(0.062)
 H7C(0.062) H9A(0.054) H9B(0.054) H9C(0.054) H10A(0.063) H10B(0.063)
 H10C(0.063) H11A(0.05) H11B(0.05) H11C(0.05) H13A(0.046) H13B(0.046)
 H13C(0.046) H14A(0.046) H14B(0.046) H14C(0.046) H15A(0.048) H15B(0.048)
 H15C(0.048) H61(0.047) H62(0.047) H63(0.048) H64(0.05) H65(0.044) H66(0.041)
 H73(0.055) H74(0.06) H75(0.064) H76(0.066) H77(0.061) H78(0.054) H67(0.04)
 H68(0.041) H69(0.041) H70(0.041) H71(0.043) H72(0.042)
 Fixed X: H33(0.6263) H34(0.6911) H35A(1.0772) H35B(1.0828) H35C(1.1021)
 H35D(1.0362) H36A(0.957) H36B(0.9534) H36C(1.0616) H36D(0.9773) H37A(1.1325)
 H37B(1.0615) H37C(1.1281) H37D(1.1408) H37E(1.099) H37F(1.189) H39A(0.6461)
 H39B(0.7577) H39C(0.6931) H40A(0.712) H40B(0.6175) H40C(0.6706) H41A(0.9052)
 H41B(0.8851) H41C(0.8386) H43A(0.7811) H43B(0.7859) H43C(0.8677) H44A(0.9361)
 H44B(1.0285) H44C(1.0025) H45A(1.0029) H45B(0.9048) H45C(0.9932) H18(0.4842)
 H19(0.6493) H20A(0.7072) H20B(0.6165) H21A(0.4931) H21B(0.5816) H22A(0.5568)
 H22B(0.5198) H22C(0.6398) H24A(0.3408) H24B(0.285) H24C(0.3433) H25A(0.5029)
 H25B(0.3799) H25C(0.446) H26A(0.4556) H26B(0.3982) H26C(0.5207) H28A(0.8319)
 H28B(0.9102) H28C(0.8025) H29A(0.826) H29B(0.9232) H29C(0.8422) H30A(0.7385)
 H30B(0.851) H30C(0.7516) H48(0.1247) H49(0.0208) H50A(0.3095) H50B(0.3918)
 H51A(0.5195) H51B(0.4364) H52A(0.5099) H52B(0.5389) H52C(0.4237) H54A(0.272)
 H54B(0.3569) H54C(0.3916) H55A(0.4645) H55B(0.4369) H55C(0.4905) H56A(0.2905)
 H56B(0.2392) H56C(0.357) H58A(0.2165) H58B(0.2595) H58C(0.1659) H59A(-0.0316)
 H59B(0.0334) H59C(-0.002) H60A(0.1655) H60B(0.0558) H60C(0.0661) H3(0.8813)
 H4(0.9182) H5A(0.6902) H5B(0.6519) H6A(0.6012) H6B(0.6491) H7A(0.4809)
 H7B(0.4666) H7C(0.5253) H9A(0.8848) H9B(0.7744) H9C(0.7873) H10A(0.8207)
 H10B(0.9183) H10C(0.8301) H11A(0.637) H11B(0.6558) H11C(0.648) H13A(0.8802)
 H13B(0.7691) H13C(0.8592) H14A(1.0138) H14B(1.0293) H14C(1.0069) H15A(0.7436)
 H15B(0.8418) H15C(0.8281) H61(0.2664) H62(0.3678) H63(0.4321) H64(0.3945)
 H65(0.2915) H66(0.2273) H73(0.9398) H74(1.0359) H75(1.2054) H76(1.2791)
 H77(1.183) H78(1.0148) H67(0.5388) H68(0.6234) H69(0.7524) H70(0.8001)
 H71(0.7159) H72(0.5835)
 Fixed Y: H33(0.8493) H34(0.8535) H35A(0.8494) H35B(0.8488) H35C(0.8577)
 H35D(0.8369) H36A(0.8098) H36B(0.8103) H36C(0.8286) H36D(0.8099) H37A(0.7934)
 H37B(0.7682) H37C(0.7935) H37D(0.782) H37E(0.7816) H37F(0.8057) H39A(0.8261)
 H39B(0.812) H39C(0.8296) H40A(0.9084) H40B(0.884) H40C(0.8911) H41A(0.8499)
 H41B(0.8876) H41C(0.8669) H43A(0.8618) H43B(0.8983) H43C(0.885) H44A(0.9159)
 H44B(0.891) H44C(0.9051) H45A(0.8342) H45B(0.8226) H45C(0.8429) H18(0.7862)
 H19(0.779) H20A(0.6676) H20B(0.6628) H21A(0.6737) H21B(0.6817) H22A(0.6201)
 H22B(0.6283) H22C(0.6284) H24A(0.732) H24B(0.7506) H24C(0.7701) H25A(0.721)
 H25B(0.7202) H25C(0.7008) H26A(0.7982) H26B(0.7808) H26C(0.7784) H28A(0.781)
 H28B(0.7579) H28C(0.7671) H29A(0.7049) H29B(0.7233) H29C(0.742) H30A(0.7116)
 H30B(0.7004) H30C(0.6871) H48(0.8899) H49(0.8834) H50A(0.9173) H50B(0.8964)
 H51A(0.9114) H51B(0.934) H52A(0.9423) H52B(0.9649) H52C(0.9645) H54A(0.9231)
 H54B(0.932) H54C(0.9189) H55A(0.8879) H55B(0.8516) H55C(0.8735) H56A(0.8391)
 H56B(0.8678) H56C(0.8585) H58A(0.8286) H58B(0.8594) H58C(0.8395) H59A(0.863)
 H59B(0.8309) H59C(0.8413) H60A(0.9102) H60B(0.9127) H60C(0.8946) H3(0.4528)
 H4(0.4526) H5A(0.5734) H5B(0.5687) H6A(0.5162) H6B(0.5183) H7A(0.5573)
 H7B(0.526) H7C(0.5564) H9A(0.4758) H9B(0.4608) H9C(0.4851) H10A(0.5559)
 H10B(0.5345) H10C(0.5409) H11A(0.4944) H11B(0.5319) H11C(0.5171) H13A(0.5553)
 H13B(0.5419) H13C(0.5431) H14A(0.481) H14B(0.5182) H14C(0.5064) H15A(0.4828)
 H15B(0.4598) H15C(0.4849) H61(0.662) H62(0.6769) H63(0.6381) H64(0.5846)
 H65(0.5696) H66(0.6083) H73(0.7701) H74(0.8112) H75(0.802) H76(0.7518)
 H77(0.711) H78(0.7206) H67(0.5242) H68(0.5713) H69(0.571) H70(0.5232)
 H71(0.4759) H72(0.4766)
 Fixed Z: H33(0.6494) H34(0.8376) H35A(0.7733) H35B(0.8854) H35C(0.8352)
 H35D(0.8734) H36A(0.7186) H36B(0.8271) H36C(0.7025) H36D(0.7224) H37A(0.8046)
 H37B(0.8251) H37C(0.9126) H37D(0.7723) H37E(0.8566) H37F(0.8692) H39A(0.5232)
 H39B(0.552) H39C(0.4435) H40A(0.5534) H40B(0.5164) H40C(0.4436) H41A(0.5906)
 H41B(0.5855) H41C(0.4815) H43A(0.9974) H43B(0.9675) H43C(1.0778) H44A(0.9309)
 H44B(0.9609) H44C(1.0486) H45A(0.9823) H45B(0.9949) H45C(1.0847) H18(0.6117)
 H19(0.7669) H20A(0.6129) H20B(0.4986) H21A(0.5545) H21B(0.6684) H22A(0.574)
 H22B(0.6593) H22C(0.6898) H24A(0.4877) H24B(0.3801) H24C(0.4858) H25A(0.3615)
 H25B(0.3094) H25C(0.4139) H26A(0.4255) H26B(0.3157) H26C(0.3812) H28A(0.7829)
 H28B(0.8718) H28C(0.8686) H29A(0.6651) H29B(0.7515) H29C(0.6515) H30A(0.856)
 H30B(0.8767) H30C(0.7785) H48(0.6664) H49(0.4782) H50A(0.4589) H50B(0.4417)
 H51A(0.6106) H51B(0.621) H52A(0.4707) H52B(0.5689) H52C(0.4772) H54A(0.7845)
 H54B(0.7479) H54C(0.8625) H55A(0.7286) H55B(0.7386) H55C(0.8396) H56A(0.779)
 H56B(0.8117) H56C(0.8833) H58A(0.3898) H58B(0.3569) H58C(0.2713) H59A(0.3289)
 H59B(0.3731) H59C(0.2558) H60A(0.3185) H60B(0.3178) H60C(0.226) H3(0.9246)
 H4(0.7759) H5A(0.6585) H5B(0.7444) H6A(0.6899) H6B(0.6104) H7A(0.5931)
 H7B(0.525) H7C(0.5109) H9A(1.0661) H9B(0.993) H9C(1.083) H10A(0.9689)
 H10B(1.0401) H10C(1.0741) H11A(0.8626) H11B(0.8581) H11C(0.9557) H13A(0.6663)
 H13B(0.5877) H13C(0.5541) H14A(0.7175) H14B(0.7455) H14C(0.6325) H15A(0.552)
 H15B(0.5992) H15C(0.511) H61(0.5223) H62(0.6941) H63(0.8236) H64(0.7803)
 H65(0.6089) H66(0.4796) H73(0.5638) H74(0.5428) H75(0.5751) H76(0.6314)
 H77(0.655) H78(0.6232) H67(0.3379) H68(0.3382) H69(0.2865) H70(0.2385)
 H71(0.2388) H72(0.2869)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O5 O 0.91867(9) 0.92382(3) 0.74441(9) 0.0266(2) Uani 1 1 d . . . . .
O6 O 1.08000(9) 0.90666(3) 0.78962(9) 0.0311(3) Uani 1 1 d . . . . .
N7 N 0.95856(9) 0.87147(3) 0.77965(9) 0.0193(3) Uani 1 1 d . . . . .
N8 N 0.77624(9) 0.86006(3) 0.67716(9) 0.0182(2) Uani 1 1 d . . . . .
N9 N 0.83312(10) 0.86454(3) 0.84437(9) 0.0198(3) Uani 1 1 d . . . . .
C31 C 0.98772(12) 0.90344(4) 0.77030(11) 0.0219(3) Uani 1 1 d . . . . .
C32 C 0.86067(11) 0.86604(3) 0.76713(11) 0.0169(3) Uani 1 1 d . . . . .
C33 C 0.69487(12) 0.85420(4) 0.69845(12) 0.0237(3) Uani 1 1 d . . . . .
H33 H 0.6263 0.8493 0.6494 0.028 Uiso 1 1 calc R . . . .
C34 C 0.73023(12) 0.85664(4) 0.80112(12) 0.0244(3) Uani 1 1 d . . . . .
H34 H 0.6911 0.8535 0.8376 0.029 Uiso 1 1 calc R . . . .
C35 C 1.03586(13) 0.84623(4) 0.81079(16) 0.0382(4) Uani 1 1 d . . . . .
H35A H 1.0772 0.8494 0.7733 0.046 Uiso 0.730(5) 1 calc R . P A 1
H35B H 1.0828 0.8488 0.8854 0.046 Uiso 0.730(5) 1 calc R . P A 1
H35C H 1.1021 0.8577 0.8352 0.046 Uiso 0.270(5) 1 calc R . P A 2
H35D H 1.0362 0.8369 0.8734 0.046 Uiso 0.270(5) 1 calc R . P A 2
C36 C 0.99837(17) 0.81365(5) 0.79365(18) 0.0247(6) Uani 0.730(5) 1 d . . P A 1
H36A H 0.9570 0.8098 0.7186 0.030 Uiso 0.730(5) 1 calc R . P A 1
H36B H 0.9534 0.8103 0.8271 0.030 Uiso 0.730(5) 1 calc R . P A 1
C36A C 1.0452(4) 0.82051(14) 0.7572(5) 0.0244(18) Uani 0.270(5) 1 d . . P A 2
H36C H 1.0616 0.8286 0.7025 0.029 Uiso 0.270(5) 1 calc R . P A 2
H36D H 0.9773 0.8099 0.7224 0.029 Uiso 0.270(5) 1 calc R . P A 2
C37 C 1.0882(2) 0.79007(7) 0.8380(2) 0.0288(6) Uani 0.730(5) 1 d . . P A 1
H37A H 1.1325 0.7934 0.8046 0.043 Uiso 0.730(5) 1 calc GR . P A 1
H37B H 1.0615 0.7682 0.8251 0.043 Uiso 0.730(5) 1 calc GR . P A 1
H37C H 1.1281 0.7935 0.9126 0.043 Uiso 0.730(5) 1 calc GR . P A 1
C37A C 1.1258(8) 0.79516(19) 0.8195(6) 0.0323(18) Uani 0.270(5) 1 d . . P A 2
H37D H 1.1408 0.7820 0.7723 0.048 Uiso 0.270(5) 1 calc GR . P A 2
H37E H 1.0990 0.7816 0.8566 0.048 Uiso 0.270(5) 1 calc GR . P A 2
H37F H 1.1890 0.8057 0.8692 0.048 Uiso 0.270(5) 1 calc GR . P A 2
C38 C 0.75785(12) 0.86118(4) 0.56589(11) 0.0221(3) Uani 1 1 d . . . . .
C39 C 0.70936(15) 0.82940(5) 0.51675(15) 0.0375(4) Uani 1 1 d . . . . .
H39A H 0.6461 0.8261 0.5232 0.056 Uiso 1 1 calc GR . . . .
H39B H 0.7577 0.8120 0.5520 0.056 Uiso 1 1 calc GR . . . .
H39C H 0.6931 0.8296 0.4435 0.056 Uiso 1 1 calc GR . . . .
C40 C 0.68273(14) 0.88865(5) 0.51526(13) 0.0337(4) Uani 1 1 d . . . . .
H40A H 0.7120 0.9084 0.5534 0.051 Uiso 1 1 calc GR . . . .
H40B H 0.6175 0.8840 0.5164 0.051 Uiso 1 1 calc GR . . . .
H40C H 0.6706 0.8911 0.4436 0.051 Uiso 1 1 calc GR . . . .
C41 C 0.85537(12) 0.86690(4) 0.55487(12) 0.0273(3) Uani 1 1 d . . . . .
H41A H 0.9052 0.8499 0.5906 0.041 Uiso 1 1 calc GR . . . .
H41B H 0.8851 0.8876 0.5855 0.041 Uiso 1 1 calc GR . . . .
H41C H 0.8386 0.8669 0.4815 0.041 Uiso 1 1 calc GR . . . .
C42 C 0.89875(13) 0.87053(4) 0.95908(12) 0.0260(3) Uani 1 1 d . . . . .
C43 C 0.82697(15) 0.87973(5) 1.00449(14) 0.0364(4) Uani 1 1 d . . . . .
H43A H 0.7811 0.8618 0.9974 0.055 Uiso 1 1 calc GR . . . .
H43B H 0.7859 0.8983 0.9675 0.055 Uiso 1 1 calc GR . . . .
H43C H 0.8677 0.8850 1.0778 0.055 Uiso 1 1 calc GR . . . .
C44 C 0.97309(14) 0.89811(5) 0.97642(13) 0.0322(4) Uani 1 1 d . . . . .
H44A H 0.9361 0.9159 0.9309 0.048 Uiso 1 1 calc GR . . . .
H44B H 1.0285 0.8910 0.9609 0.048 Uiso 1 1 calc GR . . . .
H44C H 1.0025 0.9051 1.0486 0.048 Uiso 1 1 calc GR . . . .
C45 C 0.9549(2) 0.83982(5) 1.00976(15) 0.0508(6) Uani 1 1 d . . . . .
H45A H 1.0029 0.8342 0.9823 0.076 Uiso 1 1 calc GR . . . .
H45B H 0.9048 0.8226 0.9949 0.076 Uiso 1 1 calc GR . . . .
H45C H 0.9932 0.8429 1.0847 0.076 Uiso 1 1 calc GR . . . .
O3 O 0.69643(12) 0.74677(3) 0.46087(10) 0.0436(3) Uani 1 1 d . . . . .
O4 O 0.71219(14) 0.69468(3) 0.43178(11) 0.0539(4) Uani 1 1 d . . . . .
N4 N 0.64641(13) 0.70884(3) 0.53968(11) 0.0334(3) Uani 1 1 d . . . . .
N5 N 0.53157(11) 0.74939(3) 0.54682(10) 0.0252(3) Uani 1 1 d . . . . .
N6 N 0.67954(11) 0.74362(4) 0.68352(10) 0.0276(3) Uani 1 1 d . . . . .
C16 C 0.68774(18) 0.71750(4) 0.47072(14) 0.0401(5) Uani 1 1 d . . . . .
C17 C 0.62030(13) 0.73287(4) 0.58747(12) 0.0266(3) Uani 1 1 d . . . . .
C18 C 0.53600(13) 0.77120(4) 0.61984(13) 0.0267(3) Uani 1 1 d . . . . .
H18 H 0.4842 0.7862 0.6117 0.032 Uiso 1 1 calc R . . . .
C19 C 0.62613(14) 0.76743(4) 0.70412(13) 0.0296(4) Uani 1 1 d . . . . .
H19 H 0.6493 0.7790 0.7669 0.036 Uiso 1 1 calc R . . . .
C20 C 0.63806(16) 0.67527(4) 0.56286(15) 0.0371(4) Uani 1 1 d . . . . .
H20A H 0.7072 0.6676 0.6129 0.045 Uiso 1 1 calc R . . . .
H20B H 0.6165 0.6628 0.4986 0.045 Uiso 1 1 calc R . . . .
C21 C 0.56411(17) 0.66842(4) 0.60637(18) 0.0425(5) Uani 1 1 d . . . . .
H21A H 0.4931 0.6737 0.5545 0.051 Uiso 1 1 calc R . . . .
H21B H 0.5816 0.6817 0.6684 0.051 Uiso 1 1 calc R . . . .
C22 C 0.5707(2) 0.63316(5) 0.6349(2) 0.0597(7) Uani 1 1 d . . . . .
H22A H 0.5568 0.6201 0.5740 0.090 Uiso 1 1 calc GR . . . .
H22B H 0.5198 0.6283 0.6593 0.090 Uiso 1 1 calc GR . . . .
H22C H 0.6398 0.6284 0.6898 0.090 Uiso 1 1 calc GR . . . .
C23 C 0.44386(14) 0.74948(4) 0.43834(14) 0.0350(4) Uani 1 1 d . . . . .
C24 C 0.34425(16) 0.75066(6) 0.44893(19) 0.0558(6) Uani 1 1 d . . . . .
H24A H 0.3408 0.7320 0.4877 0.084 Uiso 1 1 calc GR . . . .
H24B H 0.2850 0.7506 0.3801 0.084 Uiso 1 1 calc GR . . . .
H24C H 0.3433 0.7701 0.4858 0.084 Uiso 1 1 calc GR . . . .
C25 C 0.4431(2) 0.72025(5) 0.37511(16) 0.0572(7) Uani 1 1 d . . . . .
H25A H 0.5029 0.7210 0.3615 0.086 Uiso 1 1 calc GR . . . .
H25B H 0.3799 0.7202 0.3094 0.086 Uiso 1 1 calc GR . . . .
H25C H 0.4460 0.7008 0.4139 0.086 Uiso 1 1 calc GR . . . .
C26 C 0.45564(16) 0.77941(4) 0.38547(14) 0.0390(4) Uani 1 1 d . . . . .
H26A H 0.4556 0.7982 0.4255 0.059 Uiso 1 1 calc GR . . . .
H26B H 0.3982 0.7808 0.3157 0.059 Uiso 1 1 calc GR . . . .
H26C H 0.5207 0.7784 0.3812 0.059 Uiso 1 1 calc GR . . . .
C27 C 0.78765(15) 0.73370(5) 0.75845(14) 0.0410(5) Uani 1 1 d . . . . .
C28 C 0.83750(16) 0.76249(6) 0.82647(17) 0.0548(6) Uani 1 1 d . . . . .
H28A H 0.8319 0.7810 0.7829 0.082 Uiso 1 1 calc GR . . . .
H28B H 0.9102 0.7579 0.8718 0.082 Uiso 1 1 calc GR . . . .
H28C H 0.8025 0.7671 0.8686 0.082 Uiso 1 1 calc GR . . . .
C29 C 0.85043(17) 0.72521(6) 0.70152(17) 0.0540(6) Uani 1 1 d . . . . .
H29A H 0.8260 0.7049 0.6651 0.081 Uiso 1 1 calc GR . . . .
H29B H 0.9232 0.7233 0.7515 0.081 Uiso 1 1 calc GR . . . .
H29C H 0.8422 0.7420 0.6515 0.081 Uiso 1 1 calc GR . . . .
C30 C 0.78164(17) 0.70567(6) 0.82325(15) 0.0491(6) Uani 1 1 d . . . . .
H30A H 0.7385 0.7116 0.8560 0.074 Uiso 1 1 calc GR . . . .
H30B H 0.8510 0.7004 0.8767 0.074 Uiso 1 1 calc GR . . . .
H30C H 0.7516 0.6871 0.7785 0.074 Uiso 1 1 calc GR . . . .
O7 O 0.36187(8) 0.82347(3) 0.57784(10) 0.0298(3) Uani 1 1 d . . . . .
O8 O 0.46939(8) 0.84695(3) 0.52554(9) 0.0268(2) Uani 1 1 d . . . . .
N10 N 0.34608(9) 0.87620(3) 0.53957(10) 0.0186(2) Uani 1 1 d . . . . .
N11 N 0.25282(9) 0.88242(3) 0.64097(9) 0.0178(2) Uani 1 1 d . . . . .
N12 N 0.16029(9) 0.87586(3) 0.47408(9) 0.0171(2) Uani 1 1 d . . . . .
C46 C 0.39710(11) 0.84610(4) 0.54821(12) 0.0223(3) Uani 1 1 d . . . . .
C47 C 0.25796(11) 0.87707(3) 0.55167(11) 0.0168(3) Uani 1 1 d . . . . .
C48 C 0.15034(11) 0.88576(3) 0.61816(11) 0.0188(3) Uani 1 1 d . . . . .
H48 H 0.1247 0.8899 0.6664 0.023 Uiso 1 1 calc R . . . .
C49 C 0.09360(11) 0.88205(3) 0.51552(11) 0.0185(3) Uani 1 1 d . . . . .
H49 H 0.0208 0.8834 0.4782 0.022 Uiso 1 1 calc R . . . .
C50 C 0.37189(11) 0.90397(3) 0.49457(11) 0.0200(3) Uani 1 1 d . . . . .
H50A H 0.3095 0.9173 0.4589 0.024 Uiso 1 1 calc R . . . .
H50B H 0.3918 0.8964 0.4417 0.024 Uiso 1 1 calc R . . . .
C51 C 0.45784(12) 0.92469(4) 0.57130(12) 0.0230(3) Uani 1 1 d . . . . .
H51A H 0.5195 0.9114 0.6106 0.028 Uiso 1 1 calc R . . . .
H51B H 0.4364 0.9340 0.6210 0.028 Uiso 1 1 calc R . . . .
C52 C 0.48501(13) 0.95149(4) 0.51720(13) 0.0294(4) Uani 1 1 d . . . . .
H52A H 0.5099 0.9423 0.4707 0.044 Uiso 1 1 calc GR . . . .
H52B H 0.5389 0.9649 0.5689 0.044 Uiso 1 1 calc GR . . . .
H52C H 0.4237 0.9645 0.4772 0.044 Uiso 1 1 calc GR . . . .
C53 C 0.33582(11) 0.88350(4) 0.75218(11) 0.0238(3) Uani 1 1 d . . . . .
C54 C 0.33938(16) 0.91739(5) 0.79012(16) 0.0505(6) Uani 1 1 d . . . . .
H54A H 0.2720 0.9231 0.7845 0.076 Uiso 1 1 calc GR . . . .
H54B H 0.3569 0.9320 0.7479 0.076 Uiso 1 1 calc GR . . . .
H54C H 0.3916 0.9189 0.8625 0.076 Uiso 1 1 calc GR . . . .
C55 C 0.44132(12) 0.87320(5) 0.76598(13) 0.0338(4) Uani 1 1 d . . . . .
H55A H 0.4645 0.8879 0.7286 0.051 Uiso 1 1 calc GR . . . .
H55B H 0.4369 0.8516 0.7386 0.051 Uiso 1 1 calc GR . . . .
H55C H 0.4905 0.8735 0.8396 0.051 Uiso 1 1 calc GR . . . .
C56 C 0.30269(13) 0.86014(5) 0.81188(14) 0.0398(5) Uani 1 1 d . . . . .
H56A H 0.2905 0.8391 0.7790 0.060 Uiso 1 1 calc GR . . . .
H56B H 0.2392 0.8678 0.8117 0.060 Uiso 1 1 calc GR . . . .
H56C H 0.3570 0.8585 0.8833 0.060 Uiso 1 1 calc GR . . . .
C57 C 0.12144(11) 0.86797(4) 0.36042(11) 0.0216(3) Uani 1 1 d . . . . .
C58 C 0.19769(13) 0.84698(4) 0.34304(13) 0.0319(4) Uani 1 1 d . . . . .
H58A H 0.2165 0.8286 0.3898 0.048 Uiso 1 1 calc GR . . . .
H58B H 0.2595 0.8594 0.3569 0.048 Uiso 1 1 calc GR . . . .
H58C H 0.1659 0.8395 0.2713 0.048 Uiso 1 1 calc GR . . . .
C59 C 0.02129(12) 0.84909(4) 0.32650(13) 0.0282(3) Uani 1 1 d . . . . .
H59A H -0.0316 0.8630 0.3289 0.042 Uiso 1 1 calc GR . . . .
H59B H 0.0334 0.8309 0.3731 0.042 Uiso 1 1 calc GR . . . .
H59C H -0.0020 0.8413 0.2558 0.042 Uiso 1 1 calc GR . . . .
C60 C 0.10032(13) 0.89916(4) 0.30033(12) 0.0283(3) Uani 1 1 d . . . . .
H60A H 0.1655 0.9102 0.3185 0.042 Uiso 1 1 calc GR . . . .
H60B H 0.0558 0.9127 0.3178 0.042 Uiso 1 1 calc GR . . . .
H60C H 0.0661 0.8946 0.2260 0.042 Uiso 1 1 calc GR . . . .
O1 O 0.95685(9) 0.55948(3) 0.88045(9) 0.0295(3) Uani 1 1 d . . . . .
O2 O 0.84012(11) 0.59925(3) 0.81707(10) 0.0374(3) Uani 1 1 d . . . . .
N1 N 0.78799(10) 0.54766(3) 0.78079(10) 0.0227(3) Uani 1 1 d . . . . .
N2 N 0.82282(9) 0.49856(3) 0.87769(9) 0.0189(3) Uani 1 1 d . . . . .
N3 N 0.85792(9) 0.49871(3) 0.74649(9) 0.0199(3) Uani 1 1 d . . . . .
C1 C 0.86925(13) 0.57113(4) 0.83073(12) 0.0264(3) Uani 1 1 d . . . . .
C2 C 0.81868(10) 0.51641(3) 0.79807(11) 0.0184(3) Uani 1 1 d . . . . .
C3 C 0.86750(13) 0.46972(4) 0.87654(13) 0.0264(3) Uani 1 1 d . . . . .
H3 H 0.8813 0.4528 0.9246 0.032 Uiso 1 1 calc R . . . .
C4 C 0.88811(13) 0.46966(4) 0.79576(13) 0.0272(3) Uani 1 1 d . . . . .
H4 H 0.9182 0.4526 0.7759 0.033 Uiso 1 1 calc R . . . .
C5 C 0.68443(12) 0.55773(4) 0.70651(12) 0.0258(3) Uani 1 1 d . . . . .
H5A H 0.6902 0.5734 0.6585 0.031 Uiso 1 1 calc R . . . .
H5B H 0.6519 0.5687 0.7444 0.031 Uiso 1 1 calc R . . . .
C6 C 0.61454(12) 0.53074(4) 0.64356(13) 0.0303(4) Uani 1 1 d . . . . .
H6A H 0.6012 0.5162 0.6899 0.036 Uiso 1 1 calc R . . . .
H6B H 0.6491 0.5183 0.6104 0.036 Uiso 1 1 calc R . . . .
C7 C 0.51279(14) 0.54375(5) 0.56076(15) 0.0412(5) Uani 1 1 d . . . . .
H7A H 0.4809 0.5573 0.5931 0.062 Uiso 1 1 calc GR . . . .
H7B H 0.4666 0.5260 0.5250 0.062 Uiso 1 1 calc GR . . . .
H7C H 0.5253 0.5564 0.5109 0.062 Uiso 1 1 calc GR . . . .
C8 C 0.78754(11) 0.50769(4) 0.95693(12) 0.0218(3) Uani 1 1 d . . . . .
C9 C 0.81056(15) 0.47988(5) 1.03138(14) 0.0361(4) Uani 1 1 d . . . . .
H9A H 0.8848 0.4758 1.0661 0.054 Uiso 1 1 calc GR . . . .
H9B H 0.7744 0.4608 0.9930 0.054 Uiso 1 1 calc GR . . . .
H9C H 0.7873 0.4851 1.0830 0.054 Uiso 1 1 calc GR . . . .
C10 C 0.84419(16) 0.53737(5) 1.01520(16) 0.0418(5) Uani 1 1 d . . . . .
H10A H 0.8207 0.5559 0.9689 0.063 Uiso 1 1 calc GR . . . .
H10B H 0.9183 0.5345 1.0401 0.063 Uiso 1 1 calc GR . . . .
H10C H 0.8301 0.5409 1.0741 0.063 Uiso 1 1 calc GR . . . .
C11 C 0.67177(13) 0.51327(5) 0.90356(14) 0.0331(4) Uani 1 1 d . . . . .
H11A H 0.6370 0.4944 0.8626 0.050 Uiso 1 1 calc GR . . . .
H11B H 0.6558 0.5319 0.8581 0.050 Uiso 1 1 calc GR . . . .
H11C H 0.6480 0.5171 0.9557 0.050 Uiso 1 1 calc GR . . . .
C12 C 0.87639(12) 0.50610(4) 0.65455(11) 0.0228(3) Uani 1 1 d . . . . .
C13 C 0.84326(14) 0.53957(4) 0.61186(13) 0.0304(4) Uani 1 1 d . . . . .
H13A H 0.8802 0.5553 0.6663 0.046 Uiso 1 1 calc GR . . . .
H13B H 0.7691 0.5419 0.5877 0.046 Uiso 1 1 calc GR . . . .
H13C H 0.8592 0.5431 0.5541 0.046 Uiso 1 1 calc GR . . . .
C14 C 0.99194(13) 0.50260(5) 0.69076(13) 0.0309(4) Uani 1 1 d . . . . .
H14A H 1.0138 0.4810 0.7175 0.046 Uiso 1 1 calc GR . . . .
H14B H 1.0293 0.5182 0.7455 0.046 Uiso 1 1 calc GR . . . .
H14C H 1.0069 0.5064 0.6325 0.046 Uiso 1 1 calc GR . . . .
C15 C 0.81712(14) 0.48114(4) 0.57173(13) 0.0318(4) Uani 1 1 d . . . . .
H15A H 0.7436 0.4828 0.5520 0.048 Uiso 1 1 calc GR . . . .
H15B H 0.8418 0.4598 0.5992 0.048 Uiso 1 1 calc GR . . . .
H15C H 0.8281 0.4849 0.5110 0.048 Uiso 1 1 calc GR . . . .
C61 C 0.29212(14) 0.64617(5) 0.57489(15) 0.0389(4) Uani 1 1 d . . . . .
H61 H 0.2664 0.6620 0.5223 0.047 Uiso 1 1 calc R . . . .
C62 C 0.35254(15) 0.65504(5) 0.67693(15) 0.0391(4) Uani 1 1 d . . . . .
H62 H 0.3678 0.6769 0.6941 0.047 Uiso 1 1 calc R . . . .
C63 C 0.39071(15) 0.63211(5) 0.75370(15) 0.0403(4) Uani 1 1 d . . . . .
H63 H 0.4321 0.6381 0.8236 0.048 Uiso 1 1 calc R . . . .
C64 C 0.36809(17) 0.60040(5) 0.72784(15) 0.0418(5) Uani 1 1 d . . . . .
H64 H 0.3945 0.5846 0.7803 0.050 Uiso 1 1 calc R . . . .
C65 C 0.30710(15) 0.59146(5) 0.62594(14) 0.0364(4) Uani 1 1 d . . . . .
H65 H 0.2915 0.5696 0.6089 0.044 Uiso 1 1 calc R . . . .
C66 C 0.26910(14) 0.61433(5) 0.54940(14) 0.0344(4) Uani 1 1 d . . . . .
H66 H 0.2273 0.6083 0.4796 0.041 Uiso 1 1 calc R . . . .
C73 C 1.00935(17) 0.76654(5) 0.57840(16) 0.0454(5) Uani 1 1 d . . . . .
H73 H 0.9398 0.7701 0.5638 0.055 Uiso 1 1 calc R . . . .
C74 C 1.06601(18) 0.79080(6) 0.56522(17) 0.0500(5) Uani 1 1 d . . . . .
H74 H 1.0359 0.8112 0.5428 0.060 Uiso 1 1 calc R . . . .
C75 C 1.16638(18) 0.78539(6) 0.58463(16) 0.0531(6) Uani 1 1 d . . . . .
H75 H 1.2054 0.8020 0.5751 0.064 Uiso 1 1 calc R . . . .
C76 C 1.21008(17) 0.75560(7) 0.61807(16) 0.0547(6) Uani 1 1 d . . . . .
H76 H 1.2791 0.7518 0.6314 0.066 Uiso 1 1 calc R . . . .
C77 C 1.15314(19) 0.73146(6) 0.63208(16) 0.0505(5) Uani 1 1 d . . . . .
H77 H 1.1830 0.7110 0.6550 0.061 Uiso 1 1 calc R . . . .
C78 C 1.05359(18) 0.73710(5) 0.61277(15) 0.0447(5) Uani 1 1 d . . . . .
H78 H 1.0148 0.7206 0.6232 0.054 Uiso 1 1 calc R . . . .
C67 C 0.59187(13) 0.52395(5) 0.31732(14) 0.0337(4) Uani 1 1 d . . . . .
H67 H 0.5388 0.5242 0.3379 0.040 Uiso 1 1 calc R . . . .
C68 C 0.64191(13) 0.55184(4) 0.31739(14) 0.0341(4) Uani 1 1 d . . . . .
H68 H 0.6234 0.5713 0.3382 0.041 Uiso 1 1 calc R . . . .
C69 C 0.71876(13) 0.55167(4) 0.28732(14) 0.0342(4) Uani 1 1 d . . . . .
H69 H 0.7524 0.5710 0.2865 0.041 Uiso 1 1 calc R . . . .
C70 C 0.74664(13) 0.52339(5) 0.25843(14) 0.0342(4) Uani 1 1 d . . . . .
H70 H 0.8001 0.5232 0.2385 0.041 Uiso 1 1 calc R . . . .
C71 C 0.69666(14) 0.49536(5) 0.25854(14) 0.0356(4) Uani 1 1 d . . . . .
H71 H 0.7159 0.4759 0.2388 0.043 Uiso 1 1 calc R . . . .
C72 C 0.61853(14) 0.49578(4) 0.28756(14) 0.0354(4) Uani 1 1 d . . . . .
H72 H 0.5835 0.4766 0.2869 0.042 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 C31 1.241(2) . ?
O6 C31 1.2524(19) . ?
N7 C31 1.4312(19) . ?
N7 C32 1.3754(18) . ?
N7 C35 1.460(2) . ?
N8 C32 1.3501(19) . ?
N8 C33 1.3802(19) . ?
N8 C38 1.5151(18) . ?
N9 C32 1.3566(19) . ?
N9 C34 1.379(2) . ?
N9 C42 1.5181(19) . ?
C33 H33 0.9500 . ?
C33 C34 1.343(2) . ?
C34 H34 0.9500 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 H35C 0.9900 . ?
C35 H35D 0.9900 . ?
C35 C36 1.450(3) . ?
C35 C36A 1.373(6) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C36 C37 1.530(3) . ?
C36A H36C 0.9900 . ?
C36A H36D 0.9900 . ?
C36A C37A 1.537(9) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C37A H37D 0.9800 . ?
C37A H37E 0.9800 . ?
C37A H37F 0.9800 . ?
C38 C39 1.524(2) . ?
C38 C40 1.528(2) . ?
C38 C41 1.523(2) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 C43 1.522(2) . ?
C42 C44 1.526(2) . ?
C42 C45 1.523(2) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
O3 C16 1.248(2) . ?
O4 C16 1.244(2) . ?
N4 C16 1.433(2) . ?
N4 C17 1.373(2) . ?
N4 C20 1.465(2) . ?
N5 C17 1.345(2) . ?
N5 C18 1.380(2) . ?
N5 C23 1.512(2) . ?
N6 C17 1.341(2) . ?
N6 C19 1.381(2) . ?
N6 C27 1.511(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.337(2) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.508(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.526(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.532(3) . ?
C23 C25 1.529(3) . ?
C23 C26 1.522(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.519(3) . ?
C27 C29 1.532(3) . ?
C27 C30 1.534(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
O7 C46 1.2459(19) . ?
O8 C46 1.2420(18) . ?
N10 C46 1.4414(19) . ?
N10 C47 1.3769(18) . ?
N10 C50 1.4662(18) . ?
N11 C47 1.3532(19) . ?
N11 C48 1.3847(18) . ?
N11 C53 1.5157(18) . ?
N12 C47 1.3571(18) . ?
N12 C49 1.3840(18) . ?
N12 C57 1.5188(18) . ?
C48 H48 0.9500 . ?
C48 C49 1.345(2) . ?
C49 H49 0.9500 . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C50 C51 1.515(2) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C51 C52 1.524(2) . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C53 C54 1.516(3) . ?
C53 C55 1.523(2) . ?
C53 C56 1.526(2) . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C55 H55A 0.9800 . ?
C55 H55B 0.9800 . ?
C55 H55C 0.9800 . ?
C56 H56A 0.9800 . ?
C56 H56B 0.9800 . ?
C56 H56C 0.9800 . ?
C57 C58 1.528(2) . ?
C57 C59 1.533(2) . ?
C57 C60 1.524(2) . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?
C59 H59A 0.9800 . ?
C59 H59B 0.9800 . ?
C59 H59C 0.9800 . ?
C60 H60A 0.9800 . ?
C60 H60B 0.9800 . ?
C60 H60C 0.9800 . ?
O1 C1 1.246(2) . ?
O2 C1 1.238(2) . ?
N1 C1 1.455(2) . ?
N1 C2 1.3701(19) . ?
N1 C5 1.4634(19) . ?
N2 C2 1.3564(19) . ?
N2 C3 1.377(2) . ?
N2 C8 1.5106(19) . ?
N3 C2 1.3543(19) . ?
N3 C4 1.379(2) . ?
N3 C12 1.5118(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.339(2) . ?
C4 H4 0.9500 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.519(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.524(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.520(2) . ?
C8 C10 1.520(2) . ?
C8 C11 1.523(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.521(2) . ?
C12 C14 1.529(2) . ?
C12 C15 1.530(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C61 H61 0.9500 . ?
C61 C62 1.387(3) . ?
C61 C66 1.385(3) . ?
C62 H62 0.9500 . ?
C62 C63 1.383(3) . ?
C63 H63 0.9500 . ?
C63 C64 1.379(3) . ?
C64 H64 0.9500 . ?
C64 C65 1.387(3) . ?
C65 H65 0.9500 . ?
C65 C66 1.379(3) . ?
C66 H66 0.9500 . ?
C73 H73 0.9500 . ?
C73 C74 1.378(3) . ?
C73 C78 1.377(3) . ?
C74 H74 0.9500 . ?
C74 C75 1.379(3) . ?
C75 H75 0.9500 . ?
C75 C76 1.385(4) . ?
C76 H76 0.9500 . ?
C76 C77 1.382(3) . ?
C77 H77 0.9500 . ?
C77 C78 1.370(3) . ?
C78 H78 0.9500 . ?
C67 H67 0.9500 . ?
C67 C68 1.378(3) . ?
C67 C72 1.374(3) . ?
C68 H68 0.9500 . ?
C68 C69 1.378(3) . ?
C69 H69 0.9500 . ?
C69 C70 1.380(3) . ?
C70 H70 0.9500 . ?
C70 C71 1.384(3) . ?
C71 H71 0.9500 . ?
C71 C72 1.386(3) . ?
C72 H72 0.9500 . ?

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
C31 N7 C35 119.09(13) . . ?
C32 N7 C31 118.62(12) . . ?
C32 N7 C35 122.08(13) . . ?
C32 N8 C33 108.35(12) . . ?
C32 N8 C38 131.87(12) . . ?
C33 N8 C38 119.61(12) . . ?
C32 N9 C34 107.87(12) . . ?
C32 N9 C42 128.68(13) . . ?
C34 N9 C42 123.44(13) . . ?
O5 C31 O6 129.50(15) . . ?
O5 C31 N7 115.90(13) . . ?
O6 C31 N7 114.59(14) . . ?
N8 C32 N7 126.41(13) . . ?
N8 C32 N9 107.99(12) . . ?
N9 C32 N7 125.55(13) . . ?
N8 C33 H33 126.2 . . ?
C34 C33 N8 107.60(14) . . ?
C34 C33 H33 126.2 . . ?
N9 C34 H34 125.9 . . ?
C33 C34 N9 108.16(13) . . ?
C33 C34 H34 125.9 . . ?
N7 C35 H35A 108.1 . . ?
N7 C35 H35B 108.1 . . ?
N7 C35 H35C 104.5 . . ?
N7 C35 H35D 104.5 . . ?
H35A C35 H35B 107.3 . . ?
H35C C35 H35D 105.7 . . ?
C36 C35 N7 116.81(16) . . ?
C36 C35 H35A 108.1 . . ?
C36 C35 H35B 108.1 . . ?
C36A C35 N7 131.0(3) . . ?
C36A C35 H35C 104.5 . . ?
C36A C35 H35D 104.5 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 C37 110.60(19) . . ?
H36A C36 H36B 108.1 . . ?
C37 C36 H36A 109.5 . . ?
C37 C36 H36B 109.5 . . ?
C35 C36A H36C 108.0 . . ?
C35 C36A H36D 108.0 . . ?
C35 C36A C37A 117.1(5) . . ?
H36C C36A H36D 107.3 . . ?
C37A C36A H36C 108.0 . . ?
C37A C36A H36D 108.0 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36A C37A H37D 109.5 . . ?
C36A C37A H37E 109.5 . . ?
C36A C37A H37F 109.5 . . ?
H37D C37A H37E 109.5 . . ?
H37D C37A H37F 109.5 . . ?
H37E C37A H37F 109.5 . . ?
N8 C38 C39 106.95(13) . . ?
N8 C38 C40 106.04(12) . . ?
N8 C38 C41 113.50(12) . . ?
C39 C38 C40 110.77(14) . . ?
C41 C38 C39 110.18(14) . . ?
C41 C38 C40 109.32(13) . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C38 C40 H40A 109.5 . . ?
C38 C40 H40B 109.5 . . ?
C38 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C38 C41 H41A 109.5 . . ?
C38 C41 H41B 109.5 . . ?
C38 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
N9 C42 C43 107.70(14) . . ?
N9 C42 C44 110.58(12) . . ?
N9 C42 C45 108.81(13) . . ?
C43 C42 C44 108.40(14) . . ?
C43 C42 C45 109.24(15) . . ?
C45 C42 C44 111.99(16) . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C42 C44 H44A 109.5 . . ?
C42 C44 H44B 109.5 . . ?
C42 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C42 C45 H45A 109.5 . . ?
C42 C45 H45B 109.5 . . ?
C42 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C16 N4 C20 120.67(14) . . ?
C17 N4 C16 118.13(14) . . ?
C17 N4 C20 121.10(14) . . ?
C17 N5 C18 107.78(13) . . ?
C17 N5 C23 130.36(14) . . ?
C18 N5 C23 121.41(13) . . ?
C17 N6 C19 107.98(13) . . ?
C17 N6 C27 128.59(14) . . ?
C19 N6 C27 123.38(15) . . ?
O3 C16 N4 115.25(15) . . ?
O4 C16 O3 129.62(18) . . ?
O4 C16 N4 115.09(16) . . ?
N5 C17 N4 126.14(15) . . ?
N6 C17 N4 125.26(15) . . ?
N6 C17 N5 108.60(13) . . ?
N5 C18 H18 126.0 . . ?
C19 C18 N5 107.93(14) . . ?
C19 C18 H18 126.0 . . ?
N6 C19 H19 126.2 . . ?
C18 C19 N6 107.69(14) . . ?
C18 C19 H19 126.2 . . ?
N4 C20 H20A 108.4 . . ?
N4 C20 H20B 108.4 . . ?
N4 C20 C21 115.49(15) . . ?
H20A C20 H20B 107.5 . . ?
C21 C20 H20A 108.4 . . ?
C21 C20 H20B 108.4 . . ?
C20 C21 H21A 109.8 . . ?
C20 C21 H21B 109.8 . . ?
C20 C21 C22 109.28(16) . . ?
H21A C21 H21B 108.3 . . ?
C22 C21 H21A 109.8 . . ?
C22 C21 H21B 109.8 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N5 C23 C24 106.66(16) . . ?
N5 C23 C25 113.32(15) . . ?
N5 C23 C26 106.97(14) . . ?
C25 C23 C24 109.86(18) . . ?
C26 C23 C24 110.84(16) . . ?
C26 C23 C25 109.15(17) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N6 C27 C28 106.49(16) . . ?
N6 C27 C29 111.14(15) . . ?
N6 C27 C30 108.65(17) . . ?
C28 C27 C29 108.0(2) . . ?
C28 C27 C30 110.68(17) . . ?
C29 C27 C30 111.75(17) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C46 N10 C50 120.36(12) . . ?
C47 N10 C46 119.24(12) . . ?
C47 N10 C50 118.81(12) . . ?
C47 N11 C48 108.32(12) . . ?
C47 N11 C53 131.39(12) . . ?
C48 N11 C53 120.22(12) . . ?
C47 N12 C49 108.22(12) . . ?
C47 N12 C57 129.93(12) . . ?
C49 N12 C57 121.81(12) . . ?
O7 C46 N10 114.68(13) . . ?
O8 C46 O7 130.47(14) . . ?
O8 C46 N10 114.85(13) . . ?
N11 C47 N10 126.27(13) . . ?
N11 C47 N12 107.84(12) . . ?
N12 C47 N10 125.60(13) . . ?
N11 C48 H48 126.1 . . ?
C49 C48 N11 107.77(13) . . ?
C49 C48 H48 126.1 . . ?
N12 C49 H49 126.1 . . ?
C48 C49 N12 107.77(12) . . ?
C48 C49 H49 126.1 . . ?
N10 C50 H50A 108.5 . . ?
N10 C50 H50B 108.5 . . ?
N10 C50 C51 114.94(12) . . ?
H50A C50 H50B 107.5 . . ?
C51 C50 H50A 108.5 . . ?
C51 C50 H50B 108.5 . . ?
C50 C51 H51A 109.3 . . ?
C50 C51 H51B 109.3 . . ?
C50 C51 C52 111.45(13) . . ?
H51A C51 H51B 108.0 . . ?
C52 C51 H51A 109.3 . . ?
C52 C51 H51B 109.3 . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
N11 C53 C54 107.10(13) . . ?
N11 C53 C55 113.62(13) . . ?
N11 C53 C56 106.32(13) . . ?
C54 C53 C55 110.67(15) . . ?
C54 C53 C56 111.16(17) . . ?
C55 C53 C56 107.93(14) . . ?
C53 C54 H54A 109.5 . . ?
C53 C54 H54B 109.5 . . ?
C53 C54 H54C 109.5 . . ?
H54A C54 H54B 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C53 C55 H55A 109.5 . . ?
C53 C55 H55B 109.5 . . ?
C53 C55 H55C 109.5 . . ?
H55A C55 H55B 109.5 . . ?
H55A C55 H55C 109.5 . . ?
H55B C55 H55C 109.5 . . ?
C53 C56 H56A 109.5 . . ?
C53 C56 H56B 109.5 . . ?
C53 C56 H56C 109.5 . . ?
H56A C56 H56B 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
N12 C57 C58 111.52(12) . . ?
N12 C57 C59 106.86(12) . . ?
N12 C57 C60 108.34(12) . . ?
C58 C57 C59 108.06(13) . . ?
C60 C57 C58 111.78(14) . . ?
C60 C57 C59 110.17(13) . . ?
C57 C58 H58A 109.5 . . ?
C57 C58 H58B 109.5 . . ?
C57 C58 H58C 109.5 . . ?
H58A C58 H58B 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C57 C59 H59A 109.5 . . ?
C57 C59 H59B 109.5 . . ?
C57 C59 H59C 109.5 . . ?
H59A C59 H59B 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
C57 C60 H60A 109.5 . . ?
C57 C60 H60B 109.5 . . ?
C57 C60 H60C 109.5 . . ?
H60A C60 H60B 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
C1 N1 C5 120.43(13) . . ?
C2 N1 C1 115.51(12) . . ?
C2 N1 C5 123.54(13) . . ?
C2 N2 C3 108.08(12) . . ?
C2 N2 C8 127.85(12) . . ?
C3 N2 C8 124.06(12) . . ?
C2 N3 C4 108.15(13) . . ?
C2 N3 C12 132.00(13) . . ?
C4 N3 C12 119.78(13) . . ?
O1 C1 N1 114.36(14) . . ?
O2 C1 O1 130.73(16) . . ?
O2 C1 N1 114.91(15) . . ?
N2 C2 N1 124.56(13) . . ?
N3 C2 N1 127.44(14) . . ?
N3 C2 N2 107.79(12) . . ?
N2 C3 H3 126.0 . . ?
C4 C3 N2 108.05(14) . . ?
C4 C3 H3 126.0 . . ?
N3 C4 H4 126.0 . . ?
C3 C4 N3 107.91(14) . . ?
C3 C4 H4 126.0 . . ?
N1 C5 H5A 108.6 . . ?
N1 C5 H5B 108.6 . . ?
N1 C5 C6 114.46(13) . . ?
H5A C5 H5B 107.6 . . ?
C6 C5 H5A 108.6 . . ?
C6 C5 H5B 108.6 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 C7 110.76(15) . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 C9 107.90(12) . . ?
N2 C8 C10 110.13(13) . . ?
N2 C8 C11 109.66(12) . . ?
C9 C8 C11 108.29(14) . . ?
C10 C8 C9 110.07(15) . . ?
C10 C8 C11 110.72(15) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C13 113.45(13) . . ?
N3 C12 C14 106.88(12) . . ?
N3 C12 C15 106.90(13) . . ?
C13 C12 C14 108.95(14) . . ?
C13 C12 C15 110.42(13) . . ?
C14 C12 C15 110.15(14) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C62 C61 H61 119.9 . . ?
C66 C61 H61 119.9 . . ?
C66 C61 C62 120.19(18) . . ?
C61 C62 H62 119.9 . . ?
C63 C62 C61 120.18(19) . . ?
C63 C62 H62 119.9 . . ?
C62 C63 H63 120.3 . . ?
C64 C63 C62 119.42(18) . . ?
C64 C63 H63 120.3 . . ?
C63 C64 H64 119.7 . . ?
C63 C64 C65 120.57(18) . . ?
C65 C64 H64 119.7 . . ?
C64 C65 H65 120.0 . . ?
C66 C65 C64 120.00(19) . . ?
C66 C65 H65 120.0 . . ?
C61 C66 H66 120.2 . . ?
C65 C66 C61 119.65(18) . . ?
C65 C66 H66 120.2 . . ?
C74 C73 H73 120.0 . . ?
C78 C73 H73 120.0 . . ?
C78 C73 C74 120.0(2) . . ?
C73 C74 H74 120.0 . . ?
C73 C74 C75 120.0(2) . . ?
C75 C74 H74 120.0 . . ?
C74 C75 H75 120.1 . . ?
C74 C75 C76 119.7(2) . . ?
C76 C75 H75 120.1 . . ?
C75 C76 H76 120.0 . . ?
C77 C76 C75 120.0(2) . . ?
C77 C76 H76 120.0 . . ?
C76 C77 H77 120.1 . . ?
C78 C77 C76 119.8(2) . . ?
C78 C77 H77 120.1 . . ?
C73 C78 H78 119.8 . . ?
C77 C78 C73 120.5(2) . . ?
C77 C78 H78 119.8 . . ?
C68 C67 H67 119.9 . . ?
C72 C67 H67 119.9 . . ?
C72 C67 C68 120.16(17) . . ?
C67 C68 H68 119.9 . . ?
C69 C68 C67 120.26(17) . . ?
C69 C68 H68 119.9 . . ?
C68 C69 H69 120.1 . . ?
C68 C69 C70 119.84(17) . . ?
C70 C69 H69 120.1 . . ?
C69 C70 H70 120.0 . . ?
C69 C70 C71 119.98(17) . . ?
C71 C70 H70 120.0 . . ?
C70 C71 H71 120.1 . . ?
C70 C71 C72 119.86(17) . . ?
C72 C71 H71 120.1 . . ?
C67 C72 C71 119.89(17) . . ?
C67 C72 H72 120.1 . . ?
C71 C72 H72 120.1 . . ?

_olex2_date_sample_data_collection 2018-01-02
_olex2_date_sample_submission    2018-01-02
_olex2_submission_original_sample_id lw180102
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_compound6b
_database_code_depnum_ccdc_archive 'CCDC 1880248'
_audit_update_record             
;
2018-11-21 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;
_audit_creation_date             2018-11-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H29 N3 O2'
_chemical_formula_sum            'C16 H29 N3 O2'
_chemical_formula_weight         295.42
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   11.8565(5)
_cell_length_b                   11.8565(5)
_cell_length_c                   24.0309(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3378.2(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7366
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.99
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1144 before and 0.0650 after correction. The Ratio of minimum to maximum transmission is 0.8792. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.137
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.097
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0669
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            38933
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.444
_diffrn_reflns_theta_min         0.847
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.951
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                6490
_reflns_number_total             6906
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 2855 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.7(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         6906
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.072
_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)+(0.0320P)²+0.2743P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0763
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5080(14)
 0.4920(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C19(H19), C20(H20)
3.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C16(H16A,H16B,H16C), C12(H12A,H12B,H12C), C7(H7A,H7B,
 H7C), C27(H27A,H27B,H27C), C15(H15A,H15B,H15C), C6(H6A,H6B,H6C), C14(H14A,H14B,
 H14C), C10(H10A,H10B,H10C), C8(H8A,H8B,H8C), C30(H30A,H30B,H30C), C32(H32A,
 H32B,H32C), C31(H31A,H31B,H31C), C28(H28A,H28B,H28C), C26(H26A,H26B,H26C),
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
N3 N 0.8463(2) 0.7388(2) 0.53325(11) 0.0161(6) Uani 1 1 d . . . . .
O4 O 0.11649(18) 0.89061(19) 0.33416(10) 0.0213(5) Uani 1 1 d . . . A 1
N1 N 0.7419(2) 0.7145(2) 0.62049(11) 0.0148(6) Uani 1 1 d . . . . .
O2 O 0.58906(19) 0.7776(2) 0.57381(10) 0.0261(6) Uani 1 1 d . . . . .
N2 N 0.8531(2) 0.8779(2) 0.59298(11) 0.0151(6) Uani 1 1 d . . . . .
C2 C 0.8052(2) 0.7756(3) 0.58301(14) 0.0133(6) Uani 1 1 d . . . . .
O1 O 0.5631(2) 0.6675(2) 0.64926(11) 0.0313(6) Uani 1 1 d . . . . .
C11 C 0.9179(3) 0.9678(3) 0.68043(15) 0.0241(8) Uani 1 1 d . . . . .
H11A H 0.9228 0.8931 0.6978 0.036 Uiso 1 1 calc GR . . . .
H11B H 0.8998 1.0242 0.7088 0.036 Uiso 1 1 calc GR . . . .
H11C H 0.9904 0.9865 0.6631 0.036 Uiso 1 1 calc GR . . . .
C9 C 0.8259(3) 0.9670(3) 0.63617(14) 0.0179(7) Uani 1 1 d . . . . .
C16 C 0.7317(3) 0.5586(3) 0.52069(16) 0.0275(9) Uani 1 1 d . . . . .
H16A H 0.7792 0.5178 0.5473 0.041 Uiso 1 1 calc GR . . . .
H16B H 0.7035 0.5060 0.4925 0.041 Uiso 1 1 calc GR . . . .
H16C H 0.6679 0.5929 0.5403 0.041 Uiso 1 1 calc GR . . . .
C25 C 0.3114(3) 0.5452(3) 0.36620(14) 0.0165(7) Uani 1 1 d . . . A 1
C4 C 0.9240(3) 0.8160(3) 0.51436(14) 0.0201(7) Uani 1 1 d . . . . .
H4 H 0.9661 0.8106 0.4808 0.024 Uiso 1 1 calc R . . . .
C1 C 0.6198(3) 0.7194(3) 0.61442(15) 0.0195(7) Uani 1 1 d . . . . .
C5 C 0.8011(3) 0.6475(3) 0.66534(14) 0.0219(7) Uani 1 1 d . . . . .
C12 C 0.7074(3) 0.9504(3) 0.66050(16) 0.0236(8) Uani 1 1 d . . . . .
H12A H 0.6534 0.9383 0.6302 0.035 Uiso 1 1 calc GR . . . .
H12B H 0.6857 1.0176 0.6817 0.035 Uiso 1 1 calc GR . . . .
H12C H 0.7073 0.8846 0.6852 0.035 Uiso 1 1 calc GR . . . .
C3 C 0.9300(3) 0.9001(3) 0.55157(14) 0.0197(7) Uani 1 1 d . . . . .
H3 H 0.9787 0.9637 0.5496 0.024 Uiso 1 1 calc R . . . .
C7 C 0.7752(4) 0.6945(3) 0.72362(15) 0.0296(9) Uani 1 1 d . . . . .
H7A H 0.8060 0.7709 0.7269 0.044 Uiso 1 1 calc GR . . . .
H7B H 0.8097 0.6459 0.7518 0.044 Uiso 1 1 calc GR . . . .
H7C H 0.6934 0.6967 0.7293 0.044 Uiso 1 1 calc GR . . . .
C13 C 0.8006(3) 0.6501(3) 0.49270(13) 0.0186(7) Uani 1 1 d . . . . .
C27 C 0.2765(3) 0.4362(3) 0.39565(16) 0.0243(8) Uani 1 1 d . . . A 1
H27A H 0.3409 0.4061 0.4164 0.036 Uiso 1 1 calc GR . . A 1
H27B H 0.2519 0.3807 0.3680 0.036 Uiso 1 1 calc GR . . A 1
H27C H 0.2144 0.4520 0.4214 0.036 Uiso 1 1 calc GR . . A 1
C15 C 0.7267(3) 0.7152(3) 0.45172(15) 0.0272(8) Uani 1 1 d . . . . .
H15A H 0.6664 0.7539 0.4721 0.041 Uiso 1 1 calc GR . . . .
H15B H 0.6935 0.6627 0.4249 0.041 Uiso 1 1 calc GR . . . .
H15C H 0.7728 0.7709 0.4320 0.041 Uiso 1 1 calc GR . . . .
C6 C 0.9271(3) 0.6500(3) 0.65454(17) 0.0297(9) Uani 1 1 d . . . . .
H6A H 0.9433 0.6135 0.6188 0.045 Uiso 1 1 calc GR . . . .
H6B H 0.9664 0.6096 0.6844 0.045 Uiso 1 1 calc GR . . . .
H6C H 0.9532 0.7284 0.6534 0.045 Uiso 1 1 calc GR . . . .
C14 C 0.9009(3) 0.5953(3) 0.46368(15) 0.0251(8) Uani 1 1 d . . . . .
H14A H 0.9420 0.6524 0.4423 0.038 Uiso 1 1 calc GR . . . .
H14B H 0.8740 0.5360 0.4385 0.038 Uiso 1 1 calc GR . . . .
H14C H 0.9513 0.5622 0.4916 0.038 Uiso 1 1 calc GR . . . .
C10 C 0.8242(3) 1.0806(3) 0.60572(17) 0.0281(8) Uani 1 1 d . . . . .
H10A H 0.9000 1.0977 0.5917 0.042 Uiso 1 1 calc GR . . . .
H10B H 0.8004 1.1400 0.6315 0.042 Uiso 1 1 calc GR . . . .
H10C H 0.7713 1.0768 0.5745 0.042 Uiso 1 1 calc GR . . . .
C8 C 0.7615(3) 0.5243(3) 0.66497(16) 0.0302(9) Uani 1 1 d . . . . .
H8A H 0.6793 0.5217 0.6692 0.045 Uiso 1 1 calc GR . . . .
H8B H 0.7970 0.4836 0.6958 0.045 Uiso 1 1 calc GR . . . .
H8C H 0.7829 0.4889 0.6297 0.045 Uiso 1 1 calc GR . . . .
C18 C 0.3075(2) 0.7396(2) 0.41844(14) 0.0134(6) Uani 1 1 d . . . A 1
C17 C 0.1482(3) 0.8259(3) 0.37137(14) 0.0172(7) Uani 1 1 d . . . A 1
N4 N 0.2695(2) 0.8098(2) 0.37649(11) 0.0151(6) Uani 1 1 d . . . A 1
O3 O 0.09163(19) 0.77023(19) 0.40556(9) 0.0203(5) Uani 1 1 d . . . A 1
C30 C 0.3461(3) 0.9956(3) 0.34339(16) 0.0242(8) Uani 1 1 d . . . A 1
H30A H 0.2694 1.0188 0.3334 0.036 Uiso 1 1 calc GR . . A 1
H30B H 0.4001 1.0307 0.3178 0.036 Uiso 1 1 calc GR . . A 1
H30C H 0.3626 1.0197 0.3815 0.036 Uiso 1 1 calc GR . . A 1
C29 C 0.3559(3) 0.8663(3) 0.33936(14) 0.0185(7) Uani 1 1 d . . . A 1
C32 C 0.3387(3) 0.8321(3) 0.27870(14) 0.0265(8) Uani 1 1 d . . . A 1
H32A H 0.3548 0.7515 0.2744 0.040 Uiso 1 1 calc GR . . A 1
H32B H 0.3898 0.8758 0.2549 0.040 Uiso 1 1 calc GR . . A 1
H32C H 0.2605 0.8472 0.2678 0.040 Uiso 1 1 calc GR . . A 1
C31 C 0.4757(3) 0.8323(3) 0.35713(16) 0.0239(8) Uani 1 1 d . . . A 1
H31A H 0.4884 0.8551 0.3958 0.036 Uiso 1 1 calc GR . . A 1
H31B H 0.5308 0.8698 0.3330 0.036 Uiso 1 1 calc GR . . A 1
H31C H 0.4842 0.7504 0.3539 0.036 Uiso 1 1 calc GR . . A 1
N5 N 0.3392(2) 0.6297(2) 0.41194(11) 0.0143(6) Uani 1 1 d . . . A 1
N6 N 0.3393(2) 0.7710(2) 0.47050(10) 0.0145(5) Uani 1 1 d . . . A 1
C19 C 0.3986(3) 0.5973(3) 0.45876(14) 0.0210(7) Uani 1 1 d . . . A 1
H19 H 0.4330 0.5260 0.4646 0.025 Uiso 1 1 calc R . . A 1
C21 C 0.3166(3) 0.8788(3) 0.50357(14) 0.0186(7) Uani 1 1 d . . . A 1
C20 C 0.3989(3) 0.6842(3) 0.49438(15) 0.0209(7) Uani 1 1 d . . . A 1
H20 H 0.4341 0.6856 0.5299 0.025 Uiso 1 1 calc R . . A 1
C28 C 0.4174(3) 0.5249(3) 0.33160(15) 0.0215(7) Uani 1 1 d . . . A 1
H28A H 0.4793 0.5020 0.3561 0.032 Uiso 1 1 calc GR . . A 1
H28B H 0.4380 0.5946 0.3121 0.032 Uiso 1 1 calc GR . . A 1
H28C H 0.4029 0.4652 0.3043 0.032 Uiso 1 1 calc GR . . A 1
C26 C 0.2111(3) 0.5825(3) 0.33181(15) 0.0244(8) Uani 1 1 d . . . A 1
H26A H 0.1886 0.5213 0.3067 0.037 Uiso 1 1 calc GR . . A 1
H26B H 0.2317 0.6490 0.3099 0.037 Uiso 1 1 calc GR . . A 1
H26C H 0.1481 0.6012 0.3566 0.037 Uiso 1 1 calc GR . . A 1
C22 C 0.2183(3) 0.9463(3) 0.48015(15) 0.0208(8) Uani 1 1 d . . . A 1
H22A H 0.2398 0.9786 0.4442 0.031 Uiso 1 1 calc GR . . A 1
H22B H 0.1988 1.0071 0.5060 0.031 Uiso 1 1 calc GR . . A 1
H22C H 0.1531 0.8966 0.4752 0.031 Uiso 1 1 calc GR . . A 1
C24 C 0.4236(3) 0.9483(3) 0.50426(16) 0.0256(8) Uani 1 1 d . . . A 1
H24A H 0.4858 0.9026 0.5189 0.038 Uiso 1 1 calc GR . . A 1
H24B H 0.4127 1.0147 0.5280 0.038 Uiso 1 1 calc GR . . A 1
H24C H 0.4417 0.9727 0.4663 0.038 Uiso 1 1 calc GR . . A 1
C23 C 0.2863(3) 0.8416(3) 0.56257(15) 0.0311(9) Uani 1 1 d . . . A 1
H23A H 0.2257 0.7855 0.5610 0.047 Uiso 1 1 calc GR . . A 1
H23B H 0.2610 0.9071 0.5841 0.047 Uiso 1 1 calc GR . . A 1
H23C H 0.3528 0.8084 0.5804 0.047 Uiso 1 1 calc GR . . A 1


_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
N3 C2 1.363(4) . ?
N3 C4 1.376(4) . ?
N3 C13 1.533(4) . ?
O4 C17 1.237(4) . ?
N1 C2 1.378(4) . ?
N1 C1 1.456(4) . ?
N1 C5 1.512(4) . ?
O2 C1 1.249(4) . ?
N2 C2 1.361(4) . ?
N2 C9 1.515(4) . ?
N2 C3 1.375(4) . ?
O1 C1 1.237(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 C9 1.523(5) . ?
C9 C12 1.535(5) . ?
C9 C10 1.533(5) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 C13 1.515(5) . ?
C25 C27 1.530(5) . ?
C25 N5 1.524(4) . ?
C25 C28 1.526(5) . ?
C25 C26 1.514(4) . ?
C4 H4 0.9500 . ?
C4 C3 1.342(5) . ?
C5 C7 1.538(5) . ?
C5 C6 1.518(5) . ?
C5 C8 1.534(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C3 H3 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C13 C15 1.528(5) . ?
C13 C14 1.524(5) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C18 N4 1.383(4) . ?
C18 N5 1.365(4) . ?
C18 N6 1.359(4) . ?
C17 N4 1.456(4) . ?
C17 O3 1.250(4) . ?
N4 C29 1.515(4) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C30 C29 1.541(4) . ?
C29 C32 1.527(5) . ?
C29 C31 1.536(5) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
N5 C19 1.381(4) . ?
N6 C21 1.529(4) . ?
N6 C20 1.374(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.340(5) . ?
C21 C22 1.521(4) . ?
C21 C24 1.513(5) . ?
C21 C23 1.528(5) . ?
C20 H20 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C2 N3 C4 108.4(3) . . ?
C2 N3 C13 130.6(3) . . ?
C4 N3 C13 118.9(3) . . ?
C2 N1 C1 117.1(3) . . ?
C2 N1 C5 119.3(3) . . ?
C1 N1 C5 123.6(3) . . ?
C2 N2 C9 130.7(3) . . ?
C2 N2 C3 108.7(3) . . ?
C3 N2 C9 120.2(3) . . ?
N3 C2 N1 126.8(3) . . ?
N2 C2 N3 106.9(3) . . ?
N2 C2 N1 125.5(3) . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
N2 C9 C11 109.3(3) . . ?
N2 C9 C12 111.5(3) . . ?
N2 C9 C10 106.7(3) . . ?
C11 C9 C12 113.0(3) . . ?
C11 C9 C10 109.7(3) . . ?
C10 C9 C12 106.4(3) . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
N5 C25 C27 106.3(3) . . ?
N5 C25 C28 108.5(3) . . ?
C28 C25 C27 110.0(3) . . ?
C26 C25 C27 106.7(3) . . ?
C26 C25 N5 111.8(3) . . ?
C26 C25 C28 113.3(3) . . ?
N3 C4 H4 126.0 . . ?
C3 C4 N3 108.1(3) . . ?
C3 C4 H4 126.0 . . ?
O2 C1 N1 113.0(3) . . ?
O1 C1 N1 116.9(3) . . ?
O1 C1 O2 130.2(3) . . ?
N1 C5 C7 111.5(3) . . ?
N1 C5 C6 109.0(3) . . ?
N1 C5 C8 110.8(3) . . ?
C6 C5 C7 110.2(3) . . ?
C6 C5 C8 108.6(3) . . ?
C8 C5 C7 106.8(3) . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C3 H3 126.1 . . ?
C4 C3 N2 107.8(3) . . ?
C4 C3 H3 126.1 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C16 C13 N3 113.5(3) . . ?
C16 C13 C15 109.8(3) . . ?
C16 C13 C14 108.6(3) . . ?
C15 C13 N3 105.4(2) . . ?
C14 C13 N3 107.9(3) . . ?
C14 C13 C15 111.6(3) . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N5 C18 N4 125.5(3) . . ?
N6 C18 N4 126.6(3) . . ?
N6 C18 N5 106.9(3) . . ?
O4 C17 N4 116.3(3) . . ?
O4 C17 O3 129.8(3) . . ?
O3 C17 N4 113.9(3) . . ?
C18 N4 C17 117.6(3) . . ?
C18 N4 C29 118.4(2) . . ?
C17 N4 C29 124.0(3) . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
N4 C29 C30 110.6(3) . . ?
N4 C29 C32 110.8(3) . . ?
N4 C29 C31 110.2(3) . . ?
C32 C29 C30 108.3(3) . . ?
C32 C29 C31 108.6(3) . . ?
C31 C29 C30 108.3(3) . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C18 N5 C25 130.6(3) . . ?
C18 N5 C19 108.2(3) . . ?
C19 N5 C25 121.0(2) . . ?
C18 N6 C21 131.2(3) . . ?
C18 N6 C20 108.8(3) . . ?
C20 N6 C21 120.0(3) . . ?
N5 C19 H19 126.0 . . ?
C20 C19 N5 107.9(3) . . ?
C20 C19 H19 126.0 . . ?
C22 C21 N6 112.5(3) . . ?
C22 C21 C23 108.4(3) . . ?
C24 C21 N6 108.3(3) . . ?
C24 C21 C22 111.1(3) . . ?
C24 C21 C23 110.1(3) . . ?
C23 C21 N6 106.4(3) . . ?
N6 C20 H20 126.0 . . ?
C19 C20 N6 107.9(3) . . ?
C19 C20 H20 126.0 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_olex2_date_sample_data_collection 2018-11-06
_olex2_date_sample_submission    2018-11-06
_olex2_submission_original_sample_id lw181106
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.5080(14)
2 0.4920(14)

