# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

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

data_2aocb
_database_code_depnum_ccdc_archive 'CCDC 1964753'
loop_
_audit_author_name
_audit_author_address
'Yu Hai'
;Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2019-11-10 deposited with the CCDC.	2020-01-31 downloaded from the CCDC.
;
_audit_creation_date             2019-05-25
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C14 H16 N O2, C6 H14 N'
_chemical_formula_sum            'C20 H30 N2 O2'
_chemical_formula_weight         330.46
_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                   11.012(9)
_cell_length_b                   16.138(13)
_cell_length_c                   11.225(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.899(12)
_cell_angle_gamma                90
_cell_volume                     1980(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4414
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.1445
_cell_measurement_theta_min      2.2209
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.108
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13753
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.183
_diffrn_reflns_theta_min         2.221
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2845
_reflns_number_total             3872
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3872
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0547
_refine_ls_restrained_S_all      1.093
_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)+(0.0722P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1445
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C10(H10A,H10B), C9(H9A,H9B), C8(H8A,H8B), C7(H7A,H7B), C5(H5A,
 H5B), C4(H4A,H4B), C3(H3A,H3B), C2(H2A,H2B), C1(H1D,H1E)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C15(H15), C14(H14), C13(H13), C12(H12)
2.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_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
N2 N 0.05469(12) 0.21014(8) 0.84322(13) 0.0463(4) Uani 1 1 d . . . . .
O2 O -0.21740(12) 0.42739(8) 0.55510(11) 0.0613(4) Uani 1 1 d . . . . .
C20 C -0.19671(14) 0.34482(9) 0.73137(14) 0.0403(4) Uani 1 1 d . . . . .
C19 C -0.14354(15) 0.39579(10) 0.63588(14) 0.0434(4) Uani 1 1 d . . . . .
O1 O -0.02978(12) 0.40335(8) 0.64195(12) 0.0663(4) Uani 1 1 d . . . . .
C18 C -0.12634(14) 0.29350(9) 0.81426(14) 0.0416(4) Uani 1 1 d . . . . .
C17 C 0.00775(15) 0.28011(10) 0.81745(15) 0.0458(4) Uani 1 1 d . . . . .
H17 H 0.0576 0.3239 0.8002 0.055 Uiso 1 1 calc R . . . .
C16 C 0.18911(14) 0.20335(10) 0.85715(16) 0.0466(4) Uani 1 1 d . . . . .
H16 H 0.2239 0.2545 0.8288 0.056 Uiso 1 1 calc R . . . .
C15 C -0.32235(15) 0.34899(11) 0.73597(16) 0.0521(4) Uani 1 1 d . . . . .
H15 H -0.3699 0.3821 0.6809 0.062 Uiso 1 1 calc R . . . .
C14 C -0.18466(16) 0.25134(11) 0.90022(16) 0.0520(5) Uani 1 1 d . . . . .
H14 H -0.1380 0.2190 0.9570 0.062 Uiso 1 1 calc R . . . .
C13 C -0.30926(17) 0.25623(12) 0.90345(18) 0.0617(5) Uani 1 1 d . . . . .
H13 H -0.3462 0.2270 0.9608 0.074 Uiso 1 1 calc R . . . .
C12 C -0.37827(17) 0.30526(13) 0.82009(19) 0.0640(5) Uani 1 1 d . . . . .
H12 H -0.4625 0.3088 0.8206 0.077 Uiso 1 1 calc R . . . .
C11 C 0.23375(17) 0.19161(14) 0.98999(17) 0.0645(5) Uani 1 1 d . . . . .
H11A H 0.1935 0.1438 1.0200 0.077 Uiso 1 1 calc R . . . .
H11B H 0.2119 0.2399 1.0343 0.077 Uiso 1 1 calc R . . . .
C10 C 0.22876(16) 0.13044(13) 0.78484(18) 0.0606(5) Uani 1 1 d . . . . .
H10A H 0.2037 0.1401 0.7002 0.073 Uiso 1 1 calc R . . . .
H10B H 0.1885 0.0805 0.8078 0.073 Uiso 1 1 calc R . . . .
C9 C 0.36721(18) 0.11813(15) 0.8055(2) 0.0747(6) Uani 1 1 d . . . . .
H9A H 0.3889 0.0694 0.7621 0.090 Uiso 1 1 calc R . . . .
H9B H 0.4072 0.1656 0.7743 0.090 Uiso 1 1 calc R . . . .
C8 C 0.41239(17) 0.10772(14) 0.9383(2) 0.0765(7) Uani 1 1 d . . . . .
H8A H 0.3806 0.0564 0.9671 0.092 Uiso 1 1 calc R . . . .
H8B H 0.5010 0.1044 0.9489 0.092 Uiso 1 1 calc R . . . .
C7 C 0.37226(18) 0.17913(15) 1.0109(2) 0.0744(6) Uani 1 1 d . . . . .
H7A H 0.4126 0.2294 0.9891 0.089 Uiso 1 1 calc R . . . .
H7B H 0.3970 0.1687 1.0954 0.089 Uiso 1 1 calc R . . . .
N1 N 0.90814(12) 0.05469(8) 0.85796(12) 0.0453(4) Uani 1 1 d . . . . .
H1A H 0.9575 0.0983 0.8570 0.054 Uiso 1 1 calc GR . . . .
H1B H 0.9524 0.0084 0.8632 0.054 Uiso 1 1 calc GR . . . .
H1C H 0.8663 0.0582 0.9209 0.054 Uiso 1 1 calc GR . . . .
C6 C 0.82116(15) 0.05322(11) 0.74515(15) 0.0475(4) Uani 1 1 d . . . . .
H6 H 0.7823 0.1078 0.7348 0.057 Uiso 1 1 calc R . . . .
C5 C 0.72308(17) -0.01017(15) 0.75540(18) 0.0738(6) Uani 1 1 d . . . . .
H5A H 0.6776 0.0044 0.8212 0.089 Uiso 1 1 calc R . . . .
H5B H 0.7602 -0.0641 0.7724 0.089 Uiso 1 1 calc R . . . .
C4 C 0.88960(18) 0.03682(14) 0.63735(17) 0.0628(5) Uani 1 1 d . . . . .
H4A H 0.9365 -0.0139 0.6505 0.075 Uiso 1 1 calc R . . . .
H4B H 0.9465 0.0818 0.6294 0.075 Uiso 1 1 calc R . . . .
C3 C 0.7043(2) -0.03370(18) 0.5331(2) 0.0939(8) Uani 1 1 d . . . . .
H3A H 0.7409 -0.0883 0.5437 0.113 Uiso 1 1 calc R . . . .
H3B H 0.6475 -0.0344 0.4601 0.113 Uiso 1 1 calc R . . . .
C2 C 0.8022(2) 0.02909(17) 0.52143(18) 0.0818(7) Uani 1 1 d . . . . .
H2A H 0.7648 0.0825 0.5015 0.098 Uiso 1 1 calc R . . . .
H2B H 0.8480 0.0131 0.4565 0.098 Uiso 1 1 calc R . . . .
C1 C 0.6359(2) -0.0143(2) 0.6384(2) 0.1011(9) Uani 1 1 d . . . . .
H1D H 0.5747 -0.0567 0.6452 0.121 Uiso 1 1 calc R . . . .
H1E H 0.5941 0.0384 0.6249 0.121 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
N2 C17 1.261(2) . ?
N2 C16 1.474(2) . ?
O2 C19 1.252(2) . ?
C20 C19 1.523(2) . ?
C20 C18 1.407(2) . ?
C20 C15 1.392(2) . ?
C19 O1 1.252(2) . ?
C18 C17 1.488(2) . ?
C18 C14 1.398(2) . ?
C16 C11 1.525(3) . ?
C16 C10 1.523(3) . ?
C15 C12 1.381(3) . ?
C14 C13 1.379(3) . ?
C13 C12 1.381(3) . ?
C11 C7 1.528(3) . ?
C10 C9 1.527(3) . ?
C9 C8 1.523(3) . ?
C8 C7 1.508(3) . ?
N1 C6 1.493(2) . ?
C6 C5 1.502(3) . ?
C6 C4 1.524(3) . ?
C5 C1 1.532(3) . ?
C4 C2 1.527(3) . ?
C3 C2 1.497(4) . ?
C3 C1 1.508(4) . ?

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
C17 N2 C16 118.02(14) . . ?
C18 C20 C19 123.77(15) . . ?
C15 C20 C19 117.88(14) . . ?
C15 C20 C18 118.35(15) . . ?
O2 C19 C20 117.31(16) . . ?
O2 C19 O1 123.95(16) . . ?
O1 C19 C20 118.75(14) . . ?
C20 C18 C17 124.57(14) . . ?
C14 C18 C20 118.73(16) . . ?
C14 C18 C17 116.70(15) . . ?
N2 C17 C18 120.91(15) . . ?
N2 C16 C11 108.34(14) . . ?
N2 C16 C10 110.46(13) . . ?
C10 C16 C11 110.23(15) . . ?
C12 C15 C20 121.81(16) . . ?
C13 C14 C18 122.09(16) . . ?
C14 C13 C12 118.88(17) . . ?
C13 C12 C15 120.11(18) . . ?
C16 C11 C7 111.39(16) . . ?
C16 C10 C9 111.37(15) . . ?
C8 C9 C10 111.46(18) . . ?
C7 C8 C9 111.22(17) . . ?
C8 C7 C11 111.70(17) . . ?
N1 C6 C5 109.86(15) . . ?
N1 C6 C4 110.38(15) . . ?
C5 C6 C4 111.80(16) . . ?
C6 C5 C1 110.23(19) . . ?
C6 C4 C2 111.70(17) . . ?
C2 C3 C1 111.1(2) . . ?
C3 C2 C4 111.54(19) . . ?
C3 C1 C5 111.1(2) . . ?

_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_2focb
_database_code_depnum_ccdc_archive 'CCDC 1964754'
loop_
_audit_author_name
_audit_author_address
'Yu Hai'
;Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2019-11-10 deposited with the CCDC.	2020-01-31 downloaded from the CCDC.
;
_audit_creation_date             2019-05-28
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H14 N, C13 H15 N2 O2'
_chemical_formula_sum            'C19 H29 N3 O2'
_chemical_formula_weight         331.45
_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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   17.03(2)
_cell_length_b                   10.580(10)
_cell_length_c                   22.26(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.23(3)
_cell_angle_gamma                90
_cell_volume                     3903(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5066
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4816
_cell_measurement_theta_min      3.4154
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0563
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            15452
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.439
_diffrn_reflns_theta_min         3.415
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '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                2404
_reflns_number_total             4421
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4421
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1482
_refine_ls_R_factor_gt           0.0880
_refine_ls_restrained_S_all      1.071
_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)+(0.1378P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2275
_refine_ls_wR_factor_ref         0.2777
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2. Rigid bond restraints
 C3, N6
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
 N6, C17
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
3.a Ternary CH refined with riding coordinates:
 C5(H5), C14(H14)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C16(H16A,H16B), C18(H18A,H18B), C19(H19A,
 H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B),
 C24(H24A,H24B)
3.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C15(H15), C17(H17)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.08356(17) 0.1519(3) 0.34207(12) 0.0594(7) Uani 1 1 d . . . . .
H1A H 0.0755(19) 0.221(3) 0.3094(15) 0.071 Uiso 1 1 d R . . . .
H1B H 0.051(2) 0.082(3) 0.3362(14) 0.071 Uiso 1 1 d R . . . .
N2 N 0.26581(14) 0.5147(2) 0.15420(12) 0.0609(7) Uani 1 1 d . . . . .
C3 C 0.18788(16) 0.3332(3) 0.17028(12) 0.0525(7) Uani 1 1 d . U . . .
O4 O 0.02636(14) 0.4546(2) 0.16859(11) 0.0745(7) Uani 1 1 d . . . . .
C5 C 0.27428(18) 0.6525(3) 0.15084(14) 0.0589(7) Uani 1 1 d . . . . .
H5 H 0.2223 0.6940 0.1533 0.071 Uiso 1 1 calc R . . . .
N6 N 0.24506(15) 0.2573(3) 0.15557(13) 0.0653(7) Uani 1 1 d . U . . .
C7 C 0.12010(17) 0.2856(3) 0.18856(13) 0.0556(7) Uani 1 1 d . . . . .
O8 O 0.04139(14) 0.3493(2) 0.25733(11) 0.0758(7) Uani 1 1 d . . . . .
C9 C 0.11185(19) 0.1543(3) 0.18996(14) 0.0636(8) Uani 1 1 d . . . . .
H9 H 0.0673 0.1181 0.2028 0.076 Uiso 1 1 calc R . . . .
C10 C 0.20201(17) 0.4714(3) 0.16646(13) 0.0552(7) Uani 1 1 d . . . . .
H10 H 0.1620 0.5287 0.1734 0.066 Uiso 1 1 calc R . . . .
C11 C 0.05741(17) 0.3703(3) 0.20641(15) 0.0576(7) Uani 1 1 d . . . . .
C12 C 0.3609(2) 0.8353(3) 0.20041(15) 0.0686(9) Uani 1 1 d . . . . .
H12A H 0.3140 0.8867 0.2050 0.082 Uiso 1 1 calc R . . . .
H12B H 0.4071 0.8579 0.2345 0.082 Uiso 1 1 calc R . . . .
C13 C 0.3410(2) 0.6947(3) 0.20545(15) 0.0644(8) Uani 1 1 d . . . . .
H13A H 0.3901 0.6437 0.2067 0.077 Uiso 1 1 calc R . . . .
H13B H 0.3236 0.6800 0.2443 0.077 Uiso 1 1 calc R . . . .
C14 C 0.0747(2) 0.2166(3) 0.39964(15) 0.0702(9) Uani 1 1 d . . . . .
H14 H 0.1137 0.2887 0.4081 0.084 Uiso 1 1 calc R . . . .
C15 C 0.1679(2) 0.0775(3) 0.17293(16) 0.0710(9) Uani 1 1 d . . . . .
H15 H 0.1617 -0.0117 0.1721 0.085 Uiso 1 1 calc R . . . .
C16 C 0.2947(2) 0.6856(3) 0.08999(16) 0.0761(10) Uani 1 1 d . . . . .
H16A H 0.2489 0.6619 0.0557 0.091 Uiso 1 1 calc R . . . .
H16B H 0.3424 0.6363 0.0855 0.091 Uiso 1 1 calc R . . . .
C17 C 0.2343(2) 0.1342(3) 0.15686(17) 0.0735(9) Uani 1 1 d . U . . .
H17 H 0.2740 0.0809 0.1463 0.088 Uiso 1 1 calc R . . . .
C18 C 0.3813(2) 0.8663(3) 0.13969(18) 0.0756(9) Uani 1 1 d . . . . .
H18A H 0.4312 0.8212 0.1366 0.091 Uiso 1 1 calc R . . . .
H18B H 0.3913 0.9582 0.1376 0.091 Uiso 1 1 calc R . . . .
C19 C 0.3124(2) 0.8278(3) 0.08580(16) 0.0767(10) Uani 1 1 d . . . . .
H19A H 0.3275 0.8459 0.0463 0.092 Uiso 1 1 calc R . . . .
H19B H 0.2635 0.8773 0.0870 0.092 Uiso 1 1 calc R . . . .
C20 C -0.0097(3) 0.2685(4) 0.39187(18) 0.0886(12) Uani 1 1 d . . . . .
H20A H -0.0492 0.1988 0.3812 0.106 Uiso 1 1 calc R . . . .
H20B H -0.0206 0.3302 0.3575 0.106 Uiso 1 1 calc R . . . .
C21 C 0.0948(3) 0.1256(4) 0.45312(17) 0.1083(16) Uani 1 1 d . . . . .
H21A H 0.1517 0.0980 0.4594 0.130 Uiso 1 1 calc R . . . .
H21B H 0.0600 0.0499 0.4440 0.130 Uiso 1 1 calc R . . . .
C22 C -0.0200(4) 0.3333(6) 0.4514(2) 0.130(2) Uani 1 1 d . . . . .
H22A H 0.0163 0.4075 0.4601 0.156 Uiso 1 1 calc R . . . .
H22B H -0.0762 0.3636 0.4458 0.156 Uiso 1 1 calc R . . . .
C23 C 0.0815(5) 0.1917(7) 0.5130(2) 0.166(3) Uani 1 1 d . . . . .
H23A H 0.0896 0.1293 0.5470 0.199 Uiso 1 1 calc R . . . .
H23B H 0.1220 0.2597 0.5253 0.199 Uiso 1 1 calc R . . . .
C24 C -0.0015(5) 0.2469(7) 0.5034(3) 0.158(3) Uani 1 1 d . . . . .
H24A H -0.0415 0.1774 0.4964 0.190 Uiso 1 1 calc R . . . .
H24B H -0.0063 0.2924 0.5412 0.190 Uiso 1 1 calc R . . . .
H1C H 0.138(2) 0.117(3) 0.3421(15) 0.078(10) 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
N1 C14 1.491(4) . ?
N2 C5 1.468(4) . ?
N2 C10 1.265(4) . ?
C3 N6 1.358(4) . ?
C3 C7 1.402(4) . ?
C3 C10 1.488(4) . ?
O4 C11 1.257(4) . ?
C5 C13 1.529(5) . ?
C5 C16 1.514(5) . ?
N6 C17 1.317(4) . ?
C7 C9 1.397(4) . ?
C7 C11 1.515(4) . ?
O8 C11 1.245(4) . ?
C9 C15 1.371(5) . ?
C12 C13 1.534(4) . ?
C12 C18 1.506(5) . ?
C14 C20 1.511(5) . ?
C14 C21 1.509(5) . ?
C15 C17 1.398(5) . ?
C16 C19 1.541(5) . ?
C18 C19 1.528(5) . ?
C20 C22 1.537(6) . ?
C21 C23 1.568(7) . ?
C22 C24 1.452(8) . ?
C23 C24 1.498(9) . ?

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
C10 N2 C5 118.0(3) . . ?
N6 C3 C7 122.7(3) . . ?
N6 C3 C10 115.6(3) . . ?
C7 C3 C10 121.6(3) . . ?
N2 C5 C13 108.3(2) . . ?
N2 C5 C16 108.7(3) . . ?
C16 C5 C13 111.3(3) . . ?
C17 N6 C3 117.9(3) . . ?
C3 C7 C11 122.7(3) . . ?
C9 C7 C3 117.2(3) . . ?
C9 C7 C11 120.1(3) . . ?
C15 C9 C7 120.2(3) . . ?
N2 C10 C3 121.8(3) . . ?
O4 C11 C7 117.3(3) . . ?
O8 C11 O4 126.2(3) . . ?
O8 C11 C7 116.6(3) . . ?
C18 C12 C13 112.1(3) . . ?
C5 C13 C12 111.2(3) . . ?
N1 C14 C20 110.4(3) . . ?
N1 C14 C21 109.6(3) . . ?
C21 C14 C20 111.2(3) . . ?
C9 C15 C17 118.2(3) . . ?
C5 C16 C19 111.6(3) . . ?
N6 C17 C15 123.7(3) . . ?
C12 C18 C19 110.7(3) . . ?
C18 C19 C16 109.8(3) . . ?
C14 C20 C22 110.9(4) . . ?
C14 C21 C23 109.6(4) . . ?
C24 C22 C20 111.1(4) . . ?
C24 C23 C21 111.5(5) . . ?
C22 C24 C23 112.6(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
