# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_ic21707
_database_code_depnum_ccdc_archive 'CCDC 2235981'
loop_
_audit_author_name
_audit_author_address
'Su-Ying Chien'
;Instrumentation Center, National Taiwan University, Taipei, Taiwan
Taiwan
;
_audit_update_record             
;
2023-01-13 deposited with the CCDC.	2023-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H40 N8 O12'
_chemical_formula_weight         728.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   4.8265(7)
_cell_length_b                   11.8034(18)
_cell_length_c                   16.146(2)
_cell_angle_alpha                74.980(12)
_cell_angle_beta                 85.102(12)
_cell_angle_gamma                79.447(12)
_cell_volume                     872.7(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2200
_cell_measurement_theta_min      4.1900
_cell_measurement_theta_max      73.1660

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.159
_exptl_absorpt_coefficient_mu    0.909
_shelx_estimated_absorpt_T_min   0.611
_shelx_estimated_absorpt_T_max   0.869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.41539
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2496
_diffrn_reflns_number            10899
_diffrn_reflns_av_unetI/netI     0.0977
_diffrn_reflns_av_R_equivalents  0.1226
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.933
_diffrn_reflns_theta_max         67.980
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_point_group_measured_fraction_full 0.903
_reflns_number_total             5724
_reflns_number_gt                2944
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.816
_reflns_Friedel_fraction_max     0.811
_reflns_Friedel_fraction_full    0.812

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Classical Flack method preferred over Parsons because s.u. lower. 
;
_refine_ls_abs_structure_Flack   0.3(9)
_chemical_absolute_configuration .
_refine_ls_number_reflns         5724
_refine_ls_number_parameters     482
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.1726
_refine_ls_R_factor_gt           0.1206
_refine_ls_wR_factor_ref         0.3346
_refine_ls_wR_factor_gt          0.2821
_refine_ls_goodness_of_fit_ref   1.376
_refine_ls_restrained_S_all      1.379
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.335(2) 0.6258(9) 0.4604(7) 0.080(3) Uani 1 1 d . . . . .
O2 O 0.110(3) 0.6498(10) 0.3443(7) 0.096(3) Uani 1 1 d . . . . .
O3 O -0.391(3) 0.3654(12) 0.3028(9) 0.120(4) Uani 1 1 d . U . . .
O4 O -0.495(3) 0.2239(11) 0.4095(8) 0.100(4) Uani 1 1 d . . . . .
O5 O 0.983(2) 0.0434(10) 0.7676(7) 0.091(3) Uani 1 1 d . . . . .
O6 O 0.757(2) -0.0528(10) 0.8830(7) 0.093(3) Uani 1 1 d . . . . .
N1 N 0.248(2) 0.4568(11) 0.5962(7) 0.069(3) Uani 1 1 d D . . . .
H1A H 0.349(17) 0.526(5) 0.571(6) 0.03(2) Uiso 1 1 d D . . . .
N2 N 0.247(2) 0.3958(11) 0.6827(7) 0.070(3) Uani 1 1 d . . . . .
N3 N 0.173(2) 0.5902(11) 0.4168(8) 0.073(3) Uani 1 1 d . . . . .
N4 N -0.380(3) 0.3096(12) 0.3775(9) 0.083(3) Uani 1 1 d . . . . .
C1 C 0.094(2) 0.4209(11) 0.5429(9) 0.060(3) Uani 1 1 d . . . . .
C2 C 0.061(2) 0.4863(12) 0.4550(9) 0.062(3) Uani 1 1 d . . . . .
C3 C -0.098(3) 0.4484(12) 0.4019(9) 0.067(3) Uani 1 1 d . . . . .
H3 H -0.119985 0.490670 0.343498 0.080 Uiso 1 1 calc R U . . .
C4 C -0.218(3) 0.3512(14) 0.4346(10) 0.072(4) Uani 1 1 d . . . . .
C5 C -0.190(3) 0.2851(14) 0.5200(9) 0.073(4) Uani 1 1 d . . . . .
H5 H -0.274859 0.216050 0.540738 0.087 Uiso 1 1 calc R U . . .
C6 C -0.038(3) 0.3213(13) 0.5730(9) 0.068(4) Uani 1 1 d . . . . .
H6 H -0.022550 0.278025 0.631323 0.082 Uiso 1 1 calc R U . . .
C7 C 0.428(3) 0.4223(13) 0.7260(10) 0.071(4) Uani 1 1 d . . . . .
H7 H 0.544643 0.478996 0.698578 0.085 Uiso 1 1 calc R U . . .
C8 C 0.453(2) 0.3642(13) 0.8178(10) 0.067(3) Uani 1 1 d . . . . .
H8 H 0.264434 0.346136 0.842882 0.081 Uiso 1 1 calc R U . . .
C9 C 0.669(3) 0.2488(12) 0.8347(9) 0.066(3) Uani 1 1 d . . . . .
H9 H 0.840062 0.262075 0.796247 0.080 Uiso 1 1 calc R U . . .
C10 C 0.750(3) 0.2272(14) 0.9290(9) 0.076(4) Uani 1 1 d . . . . .
H10A H 0.956157 0.202918 0.934386 0.091 Uiso 1 1 calc R U . . .
H10B H 0.654754 0.164171 0.966968 0.091 Uiso 1 1 calc R U . . .
C11 C 0.648(3) 0.3491(15) 0.9531(10) 0.082(4) Uani 1 1 d . . . . .
H11A H 0.484492 0.344008 0.994633 0.098 Uiso 1 1 calc R U . . .
H11B H 0.801376 0.372303 0.978677 0.098 Uiso 1 1 calc R U . . .
C12 C 0.565(3) 0.4380(13) 0.8691(9) 0.072(4) Uani 1 1 d . . . . .
H12 H 0.739909 0.464245 0.838559 0.086 Uiso 1 1 calc R U . . .
C13 C 0.359(4) 0.5482(16) 0.8791(12) 0.102(5) Uani 1 1 d . . . . .
H13A H 0.304953 0.597952 0.822339 0.153 Uiso 1 1 calc R U . . .
H13B H 0.449675 0.593297 0.908984 0.153 Uiso 1 1 calc R U . . .
H13C H 0.191101 0.524255 0.912528 0.153 Uiso 1 1 calc R U . . .
C14 C 0.553(3) 0.1431(14) 0.8186(10) 0.079(4) Uani 1 1 d . . . . .
H14A H 0.410661 0.117555 0.864153 0.094 Uiso 1 1 calc R U . . .
H14B H 0.461677 0.167410 0.762665 0.094 Uiso 1 1 calc R U . . .
C15 C 0.790(3) 0.0439(13) 0.8186(10) 0.078(4) Uani 1 1 d . . . . .
C16 C 0.971(4) -0.1585(18) 0.8849(13) 0.114(6) Uani 1 1 d . . . . .
H16A H 0.994484 -0.174205 0.827785 0.171 Uiso 1 1 calc R U . . .
H16B H 0.910415 -0.226958 0.926513 0.171 Uiso 1 1 calc R U . . .
H16C H 1.150071 -0.145128 0.901592 0.171 Uiso 1 1 calc R U . . .
O7 O 0.6587(19) 0.6625(9) 0.5733(7) 0.077(3) Uani 1 1 d . . . . .
O8 O 0.865(2) 0.6437(9) 0.6923(7) 0.083(3) Uani 1 1 d . . . . .
O9 O 1.494(2) 0.8950(9) 0.7170(7) 0.079(3) Uani 1 1 d . . . . .
O10 O 1.476(2) 1.0665(10) 0.6268(7) 0.084(3) Uani 1 1 d . . . . .
O11 O 0.591(4) 0.6624(18) 0.0481(10) 0.154(6) Uani 1 1 d . U . . .
O12 O 0.341(3) 0.6092(12) 0.1662(8) 0.119(4) Uani 1 1 d . . . . .
N5 N 0.719(2) 0.8370(11) 0.4397(7) 0.066(3) Uani 1 1 d . . . . .
H5A H 0.61(2) 0.764(11) 0.468(8) 0.05(3) Uiso 1 1 d . . . . .
N6 N 0.707(2) 0.9025(12) 0.3546(8) 0.075(3) Uani 1 1 d . . . . .
N7 N 0.813(2) 0.6980(11) 0.6185(9) 0.072(3) Uani 1 1 d . . . . .
N8 N 1.405(2) 0.9701(13) 0.6513(9) 0.075(3) Uani 1 1 d . . . . .
C17 C 0.886(2) 0.8693(13) 0.4924(9) 0.066(4) Uani 1 1 d . . . . .
C18 C 0.935(3) 0.8007(12) 0.5780(9) 0.064(3) Uani 1 1 d . . . . .
C19 C 1.110(3) 0.8377(13) 0.6305(10) 0.066(3) Uani 1 1 d . . . . .
H19 H 1.142526 0.793923 0.688057 0.080 Uiso 1 1 calc R U . . .
C20 C 1.224(3) 0.9333(13) 0.5971(9) 0.065(3) Uani 1 1 d . . . . .
C21 C 1.177(3) 1.0043(14) 0.5142(10) 0.073(4) Uani 1 1 d . . . . .
H21 H 1.257546 1.074607 0.493980 0.088 Uiso 1 1 calc R U . . .
C22 C 1.010(3) 0.9708(13) 0.4618(10) 0.066(3) Uani 1 1 d . . . . .
H22 H 0.980637 1.017200 0.404701 0.080 Uiso 1 1 calc R U . . .
C23 C 0.515(3) 0.8801(14) 0.3129(9) 0.072(4) Uani 1 1 d . . . . .
H23 H 0.399173 0.823475 0.341357 0.086 Uiso 1 1 calc R U . . .
C24 C 0.472(3) 0.9417(15) 0.2211(10) 0.078(4) Uani 1 1 d . . . . .
H24 H 0.652492 0.966949 0.194539 0.094 Uiso 1 1 calc R U . . .
C25 C 0.381(3) 0.8597(16) 0.1708(11) 0.083(4) Uani 1 1 d . . . . .
H25 H 0.216479 0.825460 0.202901 0.100 Uiso 1 1 calc R U . . .
C26 C 0.272(4) 0.9512(18) 0.0876(11) 0.100(6) Uani 1 1 d . . . . .
H26A H 0.425546 0.958446 0.042656 0.120 Uiso 1 1 calc R U . . .
H26B H 0.114519 0.925717 0.065853 0.120 Uiso 1 1 calc R U . . .
C27 C 0.175(3) 1.0684(17) 0.1104(11) 0.090(5) Uani 1 1 d . . . . .
H27A H -0.030085 1.094486 0.101865 0.108 Uiso 1 1 calc R U . . .
H27B H 0.276325 1.130235 0.073807 0.108 Uiso 1 1 calc R U . . .
C28 C 0.237(3) 1.0489(14) 0.2035(10) 0.076(4) Uani 1 1 d . . . . .
H28 H 0.066780 1.025276 0.238653 0.092 Uiso 1 1 calc R U . . .
C29 C 0.300(4) 1.1594(16) 0.2267(13) 0.108(6) Uani 1 1 d . . . . .
H29A H 0.325727 1.141493 0.288555 0.162 Uiso 1 1 calc R U . . .
H29B H 0.142204 1.224926 0.210773 0.162 Uiso 1 1 calc R U . . .
H29C H 0.472655 1.182300 0.195485 0.162 Uiso 1 1 calc R U . . .
C30 C 0.612(4) 0.7574(17) 0.1605(12) 0.096(5) Uani 1 1 d . . . . .
H30A H 0.771446 0.790623 0.126325 0.115 Uiso 1 1 calc R U . . .
H30B H 0.680307 0.713351 0.217961 0.115 Uiso 1 1 calc R U . . .
C31 C 0.524(4) 0.6708(18) 0.1180(13) 0.103(5) Uani 1 1 d . . . . .
C32 C 0.254(5) 0.5184(19) 0.1323(14) 0.128(7) Uani 1 1 d . . . . .
H32A H 0.144140 0.556784 0.081245 0.192 Uiso 1 1 calc R U . . .
H32B H 0.138084 0.471615 0.176072 0.192 Uiso 1 1 calc R U . . .
H32C H 0.421455 0.465887 0.117021 0.192 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N3 1.283(15) . ?
O2 N3 1.230(15) . ?
O3 N4 1.215(17) . ?
O4 N4 1.217(15) . ?
O5 C15 1.190(16) . ?
O6 C15 1.354(18) . ?
O6 C16 1.461(19) . ?
N1 C1 1.374(17) . ?
N1 N2 1.395(16) . ?
N2 C7 1.291(18) . ?
N3 C2 1.405(18) . ?
N4 C4 1.48(2) . ?
C1 C6 1.397(18) . ?
C1 C2 1.435(18) . ?
C2 C3 1.40(2) . ?
C3 C4 1.35(2) . ?
C4 C5 1.40(2) . ?
C5 C6 1.36(2) . ?
C7 C8 1.468(19) . ?
C8 C9 1.534(19) . ?
C8 C12 1.54(2) . ?
C9 C14 1.54(2) . ?
C9 C10 1.549(19) . ?
C10 C11 1.57(2) . ?
C11 C12 1.52(2) . ?
C12 C13 1.52(2) . ?
C14 C15 1.48(2) . ?
O7 N7 1.278(16) . ?
O8 N7 1.221(15) . ?
O9 N8 1.242(16) . ?
O10 N8 1.207(17) . ?
O11 C31 1.17(2) . ?
O12 C31 1.32(2) . ?
O12 C32 1.46(2) . ?
N5 C17 1.384(18) . ?
N5 N6 1.391(16) . ?
N6 C23 1.293(17) . ?
N7 C18 1.424(18) . ?
N8 C20 1.477(17) . ?
C17 C22 1.39(2) . ?
C17 C18 1.424(18) . ?
C18 C19 1.439(18) . ?
C19 C20 1.314(19) . ?
C20 C21 1.39(2) . ?
C21 C22 1.39(2) . ?
C23 C24 1.48(2) . ?
C24 C28 1.52(2) . ?
C24 C25 1.55(2) . ?
C25 C30 1.52(2) . ?
C25 C26 1.55(2) . ?
C26 C27 1.51(3) . ?
C27 C28 1.51(2) . ?
C28 C29 1.53(2) . ?
C30 C31 1.51(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
C15 O6 C16 115.7(12) . . ?
C1 N1 N2 117.3(11) . . ?
C7 N2 N1 113.5(12) . . ?
O2 N3 O1 119.8(12) . . ?
O2 N3 C2 121.3(12) . . ?
O1 N3 C2 118.8(12) . . ?
O3 N4 O4 125.5(14) . . ?
O3 N4 C4 117.1(13) . . ?
O4 N4 C4 117.4(13) . . ?
N1 C1 C6 121.0(12) . . ?
N1 C1 C2 120.6(11) . . ?
C6 C1 C2 118.3(12) . . ?
C3 C2 N3 115.6(12) . . ?
C3 C2 C1 119.7(12) . . ?
N3 C2 C1 124.7(12) . . ?
C4 C3 C2 119.1(14) . . ?
C3 C4 C5 122.7(14) . . ?
C3 C4 N4 118.9(14) . . ?
C5 C4 N4 118.4(13) . . ?
C6 C5 C4 119.1(14) . . ?
C5 C6 C1 121.1(13) . . ?
N2 C7 C8 119.6(12) . . ?
C7 C8 C9 112.6(12) . . ?
C7 C8 C12 113.8(12) . . ?
C9 C8 C12 102.5(11) . . ?
C8 C9 C14 112.7(11) . . ?
C8 C9 C10 104.9(12) . . ?
C14 C9 C10 112.5(12) . . ?
C9 C10 C11 105.6(12) . . ?
C12 C11 C10 105.1(13) . . ?
C11 C12 C13 114.4(14) . . ?
C11 C12 C8 103.9(13) . . ?
C13 C12 C8 114.2(12) . . ?
C15 C14 C9 108.8(11) . . ?
O5 C15 O6 122.1(13) . . ?
O5 C15 C14 126.2(15) . . ?
O6 C15 C14 111.6(13) . . ?
C31 O12 C32 116.3(15) . . ?
C17 N5 N6 117.0(12) . . ?
C23 N6 N5 113.6(12) . . ?
O8 N7 O7 121.7(11) . . ?
O8 N7 C18 121.0(13) . . ?
O7 N7 C18 117.3(12) . . ?
O10 N8 O9 123.6(12) . . ?
O10 N8 C20 119.0(13) . . ?
O9 N8 C20 117.2(12) . . ?
N5 C17 C22 119.9(13) . . ?
N5 C17 C18 121.3(12) . . ?
C22 C17 C18 118.7(12) . . ?
N7 C18 C17 124.7(12) . . ?
N7 C18 C19 115.9(12) . . ?
C17 C18 C19 119.4(12) . . ?
C20 C19 C18 118.7(14) . . ?
C19 C20 C21 123.7(13) . . ?
C19 C20 N8 118.2(13) . . ?
C21 C20 N8 118.0(12) . . ?
C22 C21 C20 119.0(14) . . ?
C21 C22 C17 120.4(14) . . ?
N6 C23 C24 121.0(13) . . ?
C23 C24 C28 115.9(14) . . ?
C23 C24 C25 111.9(14) . . ?
C28 C24 C25 102.4(13) . . ?
C30 C25 C26 117.1(16) . . ?
C30 C25 C24 113.5(13) . . ?
C26 C25 C24 101.4(15) . . ?
C27 C26 C25 106.9(15) . . ?
C26 C27 C28 106.7(14) . . ?
C27 C28 C24 104.8(14) . . ?
C27 C28 C29 114.2(13) . . ?
C24 C28 C29 115.0(14) . . ?
C31 C30 C25 114.9(14) . . ?
O11 C31 O12 122.1(18) . . ?
O11 C31 C30 125.4(19) . . ?
O12 C31 C30 112.3(16) . . ?

_refine_diff_density_max         0.480
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.103

####################################################################### 
# 
# 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_ic21774
_database_code_depnum_ccdc_archive 'CCDC 2235983'
loop_
_audit_author_name
_audit_author_address
'Su-Ying Chien'
;Instrumentation Center, National Taiwan University, Taipei, Taiwan
Taiwan
;
_audit_update_record             
;
2023-01-13 deposited with the CCDC.	2023-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H46 N4 O3'
_chemical_formula_weight         606.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   8.6926(4)
_cell_length_b                   10.2171(5)
_cell_length_c                   10.4436(5)
_cell_angle_alpha                73.2229(17)
_cell_angle_beta                 86.5859(18)
_cell_angle_gamma                65.2493(15)
_cell_volume                     804.46(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9929
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      30.44

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             326
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.229
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.064
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8889
_exptl_absorpt_correction_T_max  0.9604
_exptl_absorpt_process_details   
; 
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25318
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.294
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             9341
_reflns_number_gt                7817
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.990
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.995

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker Instrument Service vV6.2.16'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker APEX4'
_computing_publication_material  'Bruker APEX4'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0233P)²+0.2650P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.047(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 3255 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.5(5)
_chemical_absolute_configuration .
_refine_ls_number_reflns         9341
_refine_ls_number_parameters     415
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1051
_refine_ls_wR_factor_gt          0.0920
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2615(4) 0.9349(3) 0.5325(2) 0.0600(7) Uani 1 1 d . . . . .
N1 N 0.2136(3) 0.9542(3) 0.3153(2) 0.0391(5) Uani 1 1 d . . . . .
N2 N 0.1783(3) 0.9990(2) -0.0516(2) 0.0314(5) Uani 1 1 d . . . . .
H2 H 0.222514 0.912164 -0.069844 0.038 Uiso 1 1 calc R U . . .
C1 C 0.3046(4) 0.8829(3) 0.4358(3) 0.0415(7) Uani 1 1 d . . . . .
C2 C 0.4630(4) 0.7404(3) 0.4511(3) 0.0429(7) Uani 1 1 d . . . . .
H2A H 0.472595 0.671278 0.542009 0.051 Uiso 1 1 calc R U . . .
H2B H 0.562801 0.764673 0.442718 0.051 Uiso 1 1 calc R U . . .
C3 C 0.4658(4) 0.6616(3) 0.3486(3) 0.0340(6) Uani 1 1 d . . . . .
H3 H 0.375628 0.623278 0.367796 0.041 Uiso 1 1 calc R U . . .
C4 C 0.6285(4) 0.5341(3) 0.3311(3) 0.0386(6) Uani 1 1 d . . . . .
H4A H 0.656342 0.441727 0.407209 0.046 Uiso 1 1 calc R U . . .
H4B H 0.725215 0.562602 0.320777 0.046 Uiso 1 1 calc R U . . .
C5 C 0.5814(4) 0.5137(3) 0.2018(3) 0.0378(6) Uani 1 1 d . . . . .
H5A H 0.517070 0.450791 0.220755 0.045 Uiso 1 1 calc R U . . .
H5B H 0.684669 0.465049 0.157213 0.045 Uiso 1 1 calc R U . . .
C6 C 0.4697(3) 0.6756(3) 0.1119(2) 0.0294(5) Uani 1 1 d . . . . .
H6 H 0.363762 0.677386 0.077392 0.035 Uiso 1 1 calc R U . . .
C7 C 0.4229(3) 0.7742(3) 0.2092(2) 0.0288(5) Uani 1 1 d . . . . .
H7 H 0.498676 0.827800 0.196184 0.035 Uiso 1 1 calc R U . . .
C8 C 0.2400(3) 0.8893(3) 0.2003(3) 0.0309(5) Uani 1 1 d . . . . .
H8 H 0.165617 0.834755 0.209747 0.037 Uiso 1 1 calc R U . . .
C9 C 0.1788(3) 1.0178(3) 0.0744(3) 0.0322(5) Uani 1 1 d . . . . .
C10 C 0.0972(3) 1.1389(3) -0.1443(3) 0.0321(5) Uani 1 1 d . . . . .
C11 C 0.0614(4) 1.1762(3) -0.2812(3) 0.0379(6) Uani 1 1 d . . . . .
H11 H 0.101119 1.101795 -0.327435 0.045 Uiso 1 1 calc R U . . .
C12 C -0.0349(4) 1.3265(3) -0.3474(3) 0.0447(7) Uani 1 1 d . . . . .
H12 H -0.064437 1.355702 -0.440711 0.054 Uiso 1 1 calc R U . . .
C13 C -0.0895(4) 1.4363(3) -0.2797(4) 0.0506(8) Uani 1 1 d . . . . .
H13 H -0.156378 1.538375 -0.327738 0.061 Uiso 1 1 calc R U . . .
C14 C -0.0483(4) 1.3993(3) -0.1452(4) 0.0484(8) Uani 1 1 d . . . . .
H14 H -0.083704 1.475427 -0.101002 0.058 Uiso 1 1 calc R U . . .
C15 C 0.0469(3) 1.2478(3) -0.0737(3) 0.0373(6) Uani 1 1 d . . . . .
C16 C 0.1023(3) 1.1677(3) 0.0641(3) 0.0376(6) Uani 1 1 d . . . . .
C17 C 0.0705(4) 1.2203(4) 0.1865(4) 0.0508(8) Uani 1 1 d . . . . .
H17A H -0.037008 1.312467 0.172169 0.061 Uiso 1 1 calc R U . . .
H17B H 0.164103 1.244035 0.206655 0.061 Uiso 1 1 calc R U . . .
C18 C 0.0595(4) 1.0954(4) 0.3015(3) 0.0531(9) Uani 1 1 d . . . . .
H18A H 0.047578 1.123876 0.385658 0.064 Uiso 1 1 calc R U . . .
H18B H -0.041854 1.080025 0.285021 0.064 Uiso 1 1 calc R U . . .
C19 C 0.5642(4) 0.7248(3) -0.0061(3) 0.0395(6) Uani 1 1 d . . . . .
H19A H 0.676773 0.706968 0.026390 0.059 Uiso 1 1 calc R U . . .
H19B H 0.500061 0.832298 -0.051468 0.059 Uiso 1 1 calc R U . . .
H19C H 0.576671 0.666746 -0.069147 0.059 Uiso 1 1 calc R U . . .
O2 O 0.3120(3) 0.4866(2) 0.8736(2) 0.0510(6) Uani 1 1 d . . . . .
N3 N 0.5445(3) 0.2685(2) 0.8957(2) 0.0323(5) Uani 1 1 d . . . . .
N4 N 0.8805(3) -0.1221(2) 0.9502(2) 0.0280(4) Uani 1 1 d . . . . .
H4 H 0.919043 -0.141601 0.874861 0.034 Uiso 1 1 calc R U . . .
C20 C 0.4019(3) 0.3834(3) 0.8263(3) 0.0346(6) Uani 1 1 d . . . . .
C21 C 0.3514(4) 0.3822(3) 0.6917(3) 0.0384(6) Uani 1 1 d . . . . .
H21A H 0.306286 0.486095 0.630363 0.046 Uiso 1 1 calc R U . . .
H21B H 0.259500 0.347520 0.701565 0.046 Uiso 1 1 calc R U . . .
C22 C 0.4976(3) 0.2814(3) 0.6308(3) 0.0318(5) Uani 1 1 d . . . . .
H22 H 0.580342 0.327862 0.606950 0.038 Uiso 1 1 calc R U . . .
C23 C 0.4607(4) 0.2436(3) 0.5087(3) 0.0410(7) Uani 1 1 d . . . . .
H23A H 0.431078 0.330638 0.427140 0.049 Uiso 1 1 calc R U . . .
H23B H 0.367704 0.210137 0.522657 0.049 Uiso 1 1 calc R U . . .
C24 C 0.6301(4) 0.1154(4) 0.5001(3) 0.0465(7) Uani 1 1 d . . . . .
H24A H 0.708503 0.155890 0.449781 0.056 Uiso 1 1 calc R U . . .
H24B H 0.613062 0.049678 0.454275 0.056 Uiso 1 1 calc R U . . .
C25 C 0.7035(4) 0.0255(3) 0.6477(3) 0.0328(5) Uani 1 1 d . . . . .
H25 H 0.822106 0.015213 0.657468 0.039 Uiso 1 1 calc R U . . .
C26 C 0.5882(3) 0.1268(3) 0.7320(2) 0.0269(5) Uani 1 1 d . . . . .
H26 H 0.501841 0.088450 0.770718 0.032 Uiso 1 1 calc R U . . .
C27 C 0.6717(3) 0.1481(3) 0.8435(2) 0.0267(5) Uani 1 1 d . . . . .
H27 H 0.760720 0.182521 0.803933 0.032 Uiso 1 1 calc R U . . .
C28 C 0.7545(3) 0.0118(3) 0.9613(2) 0.0274(5) Uani 1 1 d . . . . .
C29 C 0.9357(3) -0.2198(3) 1.0770(3) 0.0292(5) Uani 1 1 d . . . . .
C30 C 1.0597(3) -0.3679(3) 1.1172(3) 0.0359(6) Uani 1 1 d . . . . .
H30 H 1.119795 -0.417922 1.053815 0.043 Uiso 1 1 calc R U . . .
C31 C 1.0909(4) -0.4386(3) 1.2540(3) 0.0436(7) Uani 1 1 d . . . . .
H31 H 1.173634 -0.539810 1.284922 0.052 Uiso 1 1 calc R U . . .
C32 C 1.0045(4) -0.3655(4) 1.3472(3) 0.0432(7) Uani 1 1 d . . . . .
H32 H 1.032317 -0.416198 1.440209 0.052 Uiso 1 1 calc R U . . .
C33 C 0.8794(4) -0.2209(3) 1.3070(3) 0.0385(6) Uani 1 1 d . . . . .
H33 H 0.819602 -0.172604 1.371445 0.046 Uiso 1 1 calc R U . . .
C34 C 0.8415(3) -0.1458(3) 1.1699(2) 0.0307(5) Uani 1 1 d . . . . .
C35 C 0.7259(3) 0.0014(3) 1.0928(3) 0.0312(5) Uani 1 1 d . . . . .
C36 C 0.6066(4) 0.1348(3) 1.1351(3) 0.0416(7) Uani 1 1 d . . . . .
H36A H 0.651037 0.134019 1.220528 0.050 Uiso 1 1 calc R U . . .
H36B H 0.493985 0.132406 1.148258 0.050 Uiso 1 1 calc R U . . .
C37 C 0.5916(4) 0.2744(3) 1.0252(3) 0.0437(7) Uani 1 1 d . . . . .
H37A H 0.504582 0.364697 1.045762 0.052 Uiso 1 1 calc R U . . .
H37B H 0.701423 0.282570 1.021065 0.052 Uiso 1 1 calc R U . . .
C38 C 0.7059(4) -0.1301(3) 0.6829(3) 0.0446(7) Uani 1 1 d . . . . .
H38A H 0.591499 -0.120815 0.666093 0.067 Uiso 1 1 calc R U . . .
H38B H 0.743165 -0.182289 0.777829 0.067 Uiso 1 1 calc R U . . .
H38C H 0.784468 -0.187788 0.627583 0.067 Uiso 1 1 calc R U . . .
O3 O 0.1769(3) 0.7964(2) 0.7911(2) 0.0471(5) Uani 1 1 d D . . . .
H3A H 0.207(5) 0.827(4) 0.704(2) 0.071 Uiso 1 1 d D U . . .
H3B H 0.223(5) 0.6946(17) 0.797(3) 0.071 Uiso 1 1 d D U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.241(3) . ?
N1 C1 1.359(4) . ?
N1 C18 1.477(4) . ?
N1 C8 1.494(3) . ?
N2 C9 1.384(3) . ?
N2 C10 1.384(3) . ?
C1 C2 1.501(4) . ?
C2 C3 1.508(4) . ?
C3 C4 1.515(4) . ?
C3 C7 1.524(4) . ?
C4 C5 1.527(4) . ?
C5 C6 1.558(4) . ?
C6 C19 1.520(4) . ?
C6 C7 1.553(3) . ?
C7 C8 1.519(3) . ?
C8 C9 1.496(4) . ?
C9 C16 1.364(4) . ?
C10 C11 1.387(4) . ?
C10 C15 1.415(4) . ?
C11 C12 1.385(4) . ?
C12 C13 1.398(5) . ?
C13 C14 1.373(5) . ?
C14 C15 1.405(4) . ?
C15 C16 1.430(4) . ?
C16 C17 1.494(4) . ?
C17 C18 1.511(5) . ?
O2 C20 1.237(3) . ?
N3 C20 1.356(3) . ?
N3 C37 1.461(3) . ?
N3 C27 1.486(3) . ?
N4 C29 1.376(3) . ?
N4 C28 1.380(3) . ?
C20 C21 1.502(4) . ?
C21 C22 1.505(4) . ?
C22 C23 1.522(4) . ?
C22 C26 1.525(3) . ?
C23 C24 1.526(4) . ?
C24 C25 1.561(4) . ?
C25 C38 1.516(4) . ?
C25 C26 1.551(3) . ?
C26 C27 1.519(3) . ?
C27 C28 1.499(3) . ?
C28 C35 1.363(3) . ?
C29 C30 1.397(3) . ?
C29 C34 1.412(4) . ?
C30 C31 1.387(4) . ?
C31 C32 1.390(5) . ?
C32 C33 1.376(4) . ?
C33 C34 1.399(4) . ?
C34 C35 1.432(4) . ?
C35 C36 1.496(4) . ?
C36 C37 1.511(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
C1 N1 C18 118.5(2) . . ?
C1 N1 C8 124.9(2) . . ?
C18 N1 C8 115.8(2) . . ?
C9 N2 C10 109.0(2) . . ?
O1 C1 N1 121.3(3) . . ?
O1 C1 C2 119.4(3) . . ?
N1 C1 C2 119.3(2) . . ?
C1 C2 C3 112.9(2) . . ?
C2 C3 C4 120.1(2) . . ?
C2 C3 C7 109.4(2) . . ?
C4 C3 C7 102.7(2) . . ?
C3 C4 C5 101.2(2) . . ?
C4 C5 C6 105.5(2) . . ?
C19 C6 C7 113.7(2) . . ?
C19 C6 C5 111.2(2) . . ?
C7 C6 C5 104.2(2) . . ?
C8 C7 C3 108.8(2) . . ?
C8 C7 C6 117.5(2) . . ?
C3 C7 C6 104.6(2) . . ?
N1 C8 C9 107.6(2) . . ?
N1 C8 C7 109.4(2) . . ?
C9 C8 C7 116.7(2) . . ?
C16 C9 N2 109.3(2) . . ?
C16 C9 C8 127.2(3) . . ?
N2 C9 C8 123.3(2) . . ?
N2 C10 C11 129.9(2) . . ?
N2 C10 C15 107.3(2) . . ?
C11 C10 C15 122.8(3) . . ?
C12 C11 C10 117.1(3) . . ?
C11 C12 C13 121.3(3) . . ?
C14 C13 C12 121.3(3) . . ?
C13 C14 C15 119.3(3) . . ?
C14 C15 C10 118.1(3) . . ?
C14 C15 C16 134.9(3) . . ?
C10 C15 C16 106.9(2) . . ?
C9 C16 C15 107.6(2) . . ?
C9 C16 C17 120.8(3) . . ?
C15 C16 C17 131.1(3) . . ?
C16 C17 C18 107.8(3) . . ?
N1 C18 C17 110.2(3) . . ?
C20 N3 C37 117.7(2) . . ?
C20 N3 C27 125.6(2) . . ?
C37 N3 C27 116.1(2) . . ?
C29 N4 C28 108.4(2) . . ?
O2 C20 N3 120.9(3) . . ?
O2 C20 C21 120.1(2) . . ?
N3 C20 C21 119.0(2) . . ?
C20 C21 C22 112.4(2) . . ?
C21 C22 C23 118.7(2) . . ?
C21 C22 C26 110.4(2) . . ?
C23 C22 C26 103.0(2) . . ?
C22 C23 C24 101.6(2) . . ?
C23 C24 C25 106.1(2) . . ?
C38 C25 C26 114.7(2) . . ?
C38 C25 C24 110.3(2) . . ?
C26 C25 C24 104.3(2) . . ?
C27 C26 C22 107.2(2) . . ?
C27 C26 C25 118.4(2) . . ?
C22 C26 C25 104.62(19) . . ?
N3 C27 C28 107.33(19) . . ?
N3 C27 C26 109.89(19) . . ?
C28 C27 C26 116.2(2) . . ?
C35 C28 N4 109.9(2) . . ?
C35 C28 C27 126.7(2) . . ?
N4 C28 C27 123.3(2) . . ?
N4 C29 C30 129.7(2) . . ?
N4 C29 C34 108.1(2) . . ?
C30 C29 C34 122.2(2) . . ?
C31 C30 C29 116.8(3) . . ?
C30 C31 C32 121.8(3) . . ?
C33 C32 C31 121.1(3) . . ?
C32 C33 C34 119.2(3) . . ?
C33 C34 C29 118.8(2) . . ?
C33 C34 C35 134.7(3) . . ?
C29 C34 C35 106.4(2) . . ?
C28 C35 C34 107.2(2) . . ?
C28 C35 C36 121.3(2) . . ?
C34 C35 C36 131.1(2) . . ?
C35 C36 C37 107.4(2) . . ?
N3 C37 C36 110.7(2) . . ?

_refine_diff_density_max         0.195
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.038

####################################################################### 
# 
# 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_ic21750
_database_code_depnum_ccdc_archive 'CCDC 2235984'
loop_
_audit_author_name
_audit_author_address
'Su-Ying Chien'
;Instrumentation Center, National Taiwan University, Taipei, Taiwan
Taiwan
;
_audit_update_record             
;
2023-01-13 deposited with the CCDC.	2023-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H21 Cl N2 O'
_chemical_formula_weight         328.83

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.2485(2)
_cell_length_b                   10.0179(3)
_cell_length_c                   22.3054(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1619.70(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    16395
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      30.41

_exptl_crystal_description       lath
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.418
_exptl_crystal_size_min          0.034
_exptl_absorpt_coefficient_mu    0.242
_shelx_estimated_absorpt_T_min   0.880
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8231
_exptl_absorpt_correction_T_max  0.9604
_exptl_absorpt_process_details   
; 
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24516
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.229
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3712
_reflns_number_gt                3317
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker Instrument Service vV6.2.16'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker APEX4'
_computing_publication_material  'Bruker APEX4'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0245P)²+0.9832P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1314 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(3)
_chemical_absolute_configuration .
_refine_ls_number_reflns         3712
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.0975
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.58390(14) 0.39481(10) 0.53825(4) 0.0537(3) Uani 1 1 d . . . . .
O1 O 0.0013(3) 0.4275(2) 0.20719(10) 0.0398(5) Uani 1 1 d . . . . .
N1 N 0.2550(3) 0.2958(2) 0.20178(11) 0.0302(5) Uani 1 1 d . . . . .
H1 H 0.784(5) 0.372(4) 0.2554(16) 0.042(10) Uiso 1 1 d . . . . .
N2 N 0.6927(3) 0.3596(3) 0.27915(11) 0.0299(5) Uani 1 1 d . . . . .
C1 C 0.1635(4) 0.4102(3) 0.19114(12) 0.0309(6) Uani 1 1 d . . . . .
C2 C 0.2671(5) 0.5177(3) 0.15794(15) 0.0368(7) Uani 1 1 d . . . . .
H2A H 0.326753 0.577905 0.187310 0.044 Uiso 1 1 calc R U . . .
H2B H 0.178672 0.571263 0.134174 0.044 Uiso 1 1 calc R U . . .
C3 C 0.4135(4) 0.4609(3) 0.11628(13) 0.0351(7) Uani 1 1 d . . . . .
H3 H 0.482743 0.536977 0.097973 0.042 Uiso 1 1 calc R U . . .
C4 C 0.3381(5) 0.3729(4) 0.06542(15) 0.0458(8) Uani 1 1 d . . . . .
H4A H 0.210620 0.343686 0.074458 0.055 Uiso 1 1 calc R U . . .
H4B H 0.337517 0.422599 0.027058 0.055 Uiso 1 1 calc R U . . .
C5 C 0.4677(5) 0.2524(4) 0.06160(16) 0.0502(9) Uani 1 1 d . . . . .
H5A H 0.502663 0.234487 0.019451 0.060 Uiso 1 1 calc R U . . .
H5B H 0.407710 0.171767 0.078285 0.060 Uiso 1 1 calc R U . . .
C6 C 0.6384(5) 0.2905(4) 0.09889(14) 0.0396(7) Uani 1 1 d . . . . .
H6 H 0.713731 0.353431 0.074144 0.047 Uiso 1 1 calc R U . . .
C7 C 0.5516(4) 0.3725(3) 0.15030(13) 0.0310(6) Uani 1 1 d . . . . .
H7 H 0.648346 0.429923 0.169171 0.037 Uiso 1 1 calc R U . . .
C8 C 0.4593(4) 0.2857(3) 0.19889(12) 0.0287(6) Uani 1 1 d . . . . .
H8 H 0.489501 0.190608 0.189376 0.034 Uiso 1 1 calc R U . . .
C9 C 0.5228(4) 0.3111(3) 0.26234(13) 0.0292(6) Uani 1 1 d . . . . .
C10 C 0.6947(4) 0.3753(3) 0.34073(13) 0.0305(6) Uani 1 1 d . . . . .
C11 C 0.8296(4) 0.4262(3) 0.37831(14) 0.0366(7) Uani 1 1 d . . . . .
H11 H 0.943511 0.457560 0.362659 0.044 Uiso 1 1 calc R U . . .
C12 C 0.7940(5) 0.4303(3) 0.43927(14) 0.0410(7) Uani 1 1 d . . . . .
H12 H 0.885013 0.462995 0.466178 0.049 Uiso 1 1 calc R U . . .
C13 C 0.6242(4) 0.3862(3) 0.46107(14) 0.0369(7) Uani 1 1 d . . . . .
C14 C 0.4868(4) 0.3382(3) 0.42470(13) 0.0344(7) Uani 1 1 d . . . . .
H14 H 0.372087 0.309812 0.440883 0.041 Uiso 1 1 calc R U . . .
C15 C 0.5211(4) 0.3322(3) 0.36271(13) 0.0300(6) Uani 1 1 d . . . . .
C16 C 0.4139(4) 0.2913(3) 0.31201(13) 0.0309(6) Uani 1 1 d . . . . .
C17 C 0.2209(4) 0.2392(3) 0.30891(14) 0.0355(7) Uani 1 1 d . . . . .
H17A H 0.133723 0.308666 0.322841 0.043 Uiso 1 1 calc R U . . .
H17B H 0.208188 0.160539 0.335451 0.043 Uiso 1 1 calc R U . . .
C18 C 0.1749(4) 0.1999(3) 0.24439(14) 0.0348(7) Uani 1 1 d . . . . .
H18A H 0.224064 0.109557 0.236054 0.042 Uiso 1 1 calc R U . . .
H18B H 0.039325 0.197166 0.239187 0.042 Uiso 1 1 calc R U . . .
C19 C 0.7628(5) 0.1745(4) 0.11604(17) 0.0501(9) Uani 1 1 d . . . . .
H19A H 0.864836 0.207341 0.140806 0.075 Uiso 1 1 calc R U . . .
H19B H 0.812234 0.132974 0.079652 0.075 Uiso 1 1 calc R U . . .
H19C H 0.691518 0.108492 0.138710 0.075 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C13 1.748(3) . ?
O1 C1 1.241(3) . ?
N1 C1 1.345(4) . ?
N1 C18 1.471(4) . ?
N1 C8 1.486(4) . ?
N2 C9 1.376(4) . ?
N2 C10 1.383(4) . ?
C1 C2 1.507(4) . ?
C2 C3 1.521(4) . ?
C3 C7 1.537(4) . ?
C3 C4 1.537(4) . ?
C4 C5 1.532(5) . ?
C5 C6 1.539(5) . ?
C6 C19 1.519(5) . ?
C6 C7 1.544(4) . ?
C7 C8 1.542(4) . ?
C8 C9 1.510(4) . ?
C9 C16 1.375(4) . ?
C10 C11 1.385(4) . ?
C10 C15 1.418(4) . ?
C11 C12 1.385(4) . ?
C12 C13 1.395(5) . ?
C13 C14 1.372(4) . ?
C14 C15 1.406(4) . ?
C15 C16 1.432(4) . ?
C16 C17 1.495(4) . ?
C17 C18 1.529(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
C1 N1 C18 118.4(2) . . ?
C1 N1 C8 122.8(2) . . ?
C18 N1 C8 112.1(2) . . ?
C9 N2 C10 108.7(2) . . ?
O1 C1 N1 122.4(3) . . ?
O1 C1 C2 120.9(3) . . ?
N1 C1 C2 116.7(2) . . ?
C1 C2 C3 112.4(3) . . ?
C2 C3 C7 111.6(2) . . ?
C2 C3 C4 114.7(3) . . ?
C7 C3 C4 105.4(3) . . ?
C5 C4 C3 105.9(3) . . ?
C4 C5 C6 105.5(3) . . ?
C19 C6 C5 115.0(3) . . ?
C19 C6 C7 117.5(3) . . ?
C5 C6 C7 101.9(2) . . ?
C3 C7 C8 112.9(2) . . ?
C3 C7 C6 101.8(2) . . ?
C8 C7 C6 113.5(2) . . ?
N1 C8 C9 104.6(2) . . ?
N1 C8 C7 115.1(2) . . ?
C9 C8 C7 115.6(2) . . ?
C16 C9 N2 110.2(3) . . ?
C16 C9 C8 123.8(3) . . ?
N2 C9 C8 126.0(2) . . ?
N2 C10 C11 130.6(3) . . ?
N2 C10 C15 107.4(3) . . ?
C11 C10 C15 122.0(3) . . ?
C12 C11 C10 118.3(3) . . ?
C11 C12 C13 119.8(3) . . ?
C14 C13 C12 123.0(3) . . ?
C14 C13 Cl1 118.6(2) . . ?
C12 C13 Cl1 118.4(2) . . ?
C13 C14 C15 117.9(3) . . ?
C14 C15 C10 118.9(3) . . ?
C14 C15 C16 133.9(3) . . ?
C10 C15 C16 107.2(2) . . ?
C9 C16 C15 106.5(3) . . ?
C9 C16 C17 123.4(3) . . ?
C15 C16 C17 130.1(3) . . ?
C16 C17 C18 109.7(2) . . ?
N1 C18 C17 110.7(2) . . ?

_refine_diff_density_max         0.261
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.045

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

data_ic21796
_database_code_depnum_ccdc_archive 'CCDC 2236742'
loop_
_audit_author_name
_audit_author_address
'Yi-Hung Liu'
;Instrumentation Center, National Taiwan University, Taipei, Taiwan
Taiwan
;
_audit_update_record             
;
2023-01-17 deposited with the CCDC.	2023-04-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H23 N2 O1.50'
_chemical_formula_weight         303.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   8.6495(4)
_cell_length_b                   10.1461(5)
_cell_length_c                   10.4409(5)
_cell_angle_alpha                72.9361(19)
_cell_angle_beta                 86.3302(18)
_cell_angle_gamma                65.6886(17)
_cell_volume                     796.57(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9847
_cell_measurement_theta_min      4.44
_cell_measurement_theta_max      78.11

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             326
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.634
_shelx_estimated_absorpt_T_min   0.884
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.8635
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
; 
SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker AXS D8 VENTURE, PhotonIII_C28'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25517
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.439
_diffrn_reflns_theta_max         78.353
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_point_group_measured_fraction_full 0.953
_reflns_number_total             6039
_reflns_number_gt                5925
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.851
_reflns_Friedel_fraction_max     0.812
_reflns_Friedel_fraction_full    0.914

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX4'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0755P)²+0.1314P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0065(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2684 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.12(17)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6039
_refine_ls_number_parameters     412
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.1019
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3081(2) 0.48650(19) 0.87472(18) 0.0307(4) Uani 1 1 d . . . . .
N1 N 0.5439(2) 0.2704(2) 0.89548(19) 0.0219(4) Uani 1 1 d . . . . .
N2 N 0.8811(2) -0.1217(2) 0.95078(18) 0.0187(4) Uani 1 1 d . . . . .
H2 H 0.919261 -0.141367 0.875324 0.022 Uiso 1 1 calc R U . . .
C1 C 0.4000(3) 0.3842(3) 0.8271(2) 0.0221(5) Uani 1 1 d . . . . .
C2 C 0.3498(3) 0.3823(3) 0.6917(2) 0.0247(5) Uani 1 1 d . . . . .
H2A H 0.258513 0.345626 0.702148 0.030 Uiso 1 1 calc R U . . .
H2B H 0.303884 0.486716 0.630175 0.030 Uiso 1 1 calc R U . . .
C3 C 0.4974(3) 0.2825(3) 0.6303(2) 0.0213(4) Uani 1 1 d . . . . .
H3 H 0.579504 0.330903 0.605953 0.026 Uiso 1 1 calc R U . . .
C4 C 0.4619(3) 0.2437(3) 0.5084(2) 0.0264(5) Uani 1 1 d . . . . .
H4A H 0.431578 0.331490 0.426651 0.032 Uiso 1 1 calc R U . . .
H4B H 0.369747 0.208041 0.522816 0.032 Uiso 1 1 calc R U . . .
C5 C 0.6328(3) 0.1170(3) 0.4993(2) 0.0290(5) Uani 1 1 d . . . . .
H5A H 0.710706 0.159615 0.448711 0.035 Uiso 1 1 calc R U . . .
H5B H 0.617128 0.050366 0.453387 0.035 Uiso 1 1 calc R U . . .
C6 C 0.7062(3) 0.0267(3) 0.6470(2) 0.0222(5) Uani 1 1 d . . . . .
H6 H 0.824579 0.017991 0.656690 0.027 Uiso 1 1 calc R U . . .
C7 C 0.5893(3) 0.1270(2) 0.7319(2) 0.0188(4) Uani 1 1 d . . . . .
H7 H 0.503646 0.086404 0.771250 0.023 Uiso 1 1 calc R U . . .
C8 C 0.6726(3) 0.1501(2) 0.8432(2) 0.0191(4) Uani 1 1 d . . . . .
H8 H 0.761587 0.185931 0.803010 0.023 Uiso 1 1 calc R U . . .
C9 C 0.7554(3) 0.0133(2) 0.9618(2) 0.0193(4) Uani 1 1 d . . . . .
C10 C 0.9361(3) -0.2198(3) 1.0782(2) 0.0195(4) Uani 1 1 d . . . . .
C11 C 1.0601(3) -0.3683(3) 1.1185(2) 0.0237(5) Uani 1 1 d . . . . .
H11 H 1.119475 -0.418612 1.055074 0.028 Uiso 1 1 calc R U . . .
C12 C 1.0924(3) -0.4391(3) 1.2559(3) 0.0264(5) Uani 1 1 d . . . . .
H12 H 1.175043 -0.540421 1.286905 0.032 Uiso 1 1 calc R U . . .
C13 C 1.0062(3) -0.3647(3) 1.3498(2) 0.0268(5) Uani 1 1 d . . . . .
H13 H 1.034203 -0.415178 1.442994 0.032 Uiso 1 1 calc R U . . .
C14 C 0.8815(3) -0.2195(3) 1.3091(2) 0.0249(5) Uani 1 1 d . . . . .
H14 H 0.822185 -0.170647 1.373505 0.030 Uiso 1 1 calc R U . . .
C15 C 0.8431(3) -0.1447(3) 1.1714(2) 0.0207(5) Uani 1 1 d . . . . .
C16 C 0.7275(3) 0.0029(3) 1.0940(2) 0.0210(4) Uani 1 1 d . . . . .
C17 C 0.6085(3) 0.1366(3) 1.1361(2) 0.0265(5) Uani 1 1 d . . . . .
H17A H 0.653534 0.136683 1.220833 0.032 Uiso 1 1 calc R U . . .
H17B H 0.495877 0.132975 1.150773 0.032 Uiso 1 1 calc R U . . .
C18 C 0.5924(3) 0.2779(3) 1.0243(2) 0.0266(5) Uani 1 1 d . . . . .
H18A H 0.505477 0.368379 1.044831 0.032 Uiso 1 1 calc R U . . .
H18B H 0.702230 0.287420 1.018347 0.032 Uiso 1 1 calc R U . . .
C19 C 0.7091(3) -0.1313(3) 0.6830(2) 0.0282(5) Uani 1 1 d . . . . .
H19A H 0.595267 -0.123237 0.664871 0.042 Uiso 1 1 calc R U . . .
H19B H 0.743964 -0.182801 0.778482 0.042 Uiso 1 1 calc R U . . .
H19C H 0.789849 -0.189264 0.628875 0.042 Uiso 1 1 calc R U . . .
O2 O 0.2653(3) 0.9358(2) 0.53187(18) 0.0347(4) Uani 1 1 d . . . . .
N3 N 0.2169(3) 0.9547(2) 0.3148(2) 0.0251(4) Uani 1 1 d . . . . .
N4 N 0.1803(2) 0.9991(2) -0.05279(19) 0.0209(4) Uani 1 1 d . . . . .
H4 H 0.224826 0.911756 -0.070542 0.025 Uiso 1 1 calc R U . . .
C20 C 0.3075(3) 0.8841(3) 0.4351(2) 0.0262(5) Uani 1 1 d . . . . .
C21 C 0.4671(3) 0.7406(3) 0.4502(2) 0.0266(5) Uani 1 1 d . . . . .
H21A H 0.567233 0.765750 0.440248 0.032 Uiso 1 1 calc R U . . .
H21B H 0.477240 0.671100 0.541525 0.032 Uiso 1 1 calc R U . . .
C22 C 0.4681(3) 0.6612(3) 0.3482(2) 0.0229(5) Uani 1 1 d . . . . .
H22 H 0.377627 0.622109 0.368735 0.027 Uiso 1 1 calc R U . . .
C23 C 0.6315(3) 0.5332(3) 0.3302(2) 0.0247(5) Uani 1 1 d . . . . .
H23A H 0.659948 0.440515 0.406998 0.030 Uiso 1 1 calc R U . . .
H23B H 0.728420 0.562793 0.318019 0.030 Uiso 1 1 calc R U . . .
C24 C 0.5822(3) 0.5119(3) 0.2018(2) 0.0239(5) Uani 1 1 d . . . . .
H24A H 0.516913 0.448607 0.222519 0.029 Uiso 1 1 calc R U . . .
H24B H 0.684785 0.462853 0.156491 0.029 Uiso 1 1 calc R U . . .
C25 C 0.4705(3) 0.6748(2) 0.1111(2) 0.0203(4) Uani 1 1 d . . . . .
H25 H 0.364051 0.676274 0.077274 0.024 Uiso 1 1 calc R U . . .
C26 C 0.4252(3) 0.7741(3) 0.2076(2) 0.0200(4) Uani 1 1 d . . . . .
H26 H 0.501633 0.828309 0.193284 0.024 Uiso 1 1 calc R U . . .
C27 C 0.2422(3) 0.8893(3) 0.2000(2) 0.0208(4) Uani 1 1 d . . . . .
H27 H 0.167234 0.834082 0.210611 0.025 Uiso 1 1 calc R U . . .
C28 C 0.1806(3) 1.0189(3) 0.0724(2) 0.0220(5) Uani 1 1 d . . . . .
C29 C 0.0984(3) 1.1391(3) -0.1458(2) 0.0210(4) Uani 1 1 d . . . . .
C30 C 0.0622(3) 1.1760(3) -0.2833(2) 0.0238(5) Uani 1 1 d . . . . .
H30 H 0.102279 1.101343 -0.329370 0.029 Uiso 1 1 calc R U . . .
C31 C -0.0351(3) 1.3271(3) -0.3496(3) 0.0277(5) Uani 1 1 d . . . . .
H31 H -0.064377 1.356047 -0.442914 0.033 Uiso 1 1 calc R U . . .
C32 C -0.0913(3) 1.4379(3) -0.2822(3) 0.0308(6) Uani 1 1 d . . . . .
H32 H -0.159805 1.539909 -0.330338 0.037 Uiso 1 1 calc R U . . .
C33 C -0.0487(3) 1.4015(3) -0.1473(3) 0.0293(5) Uani 1 1 d . . . . .
H33 H -0.083818 1.478048 -0.103338 0.035 Uiso 1 1 calc R U . . .
C34 C 0.0472(3) 1.2497(3) -0.0760(2) 0.0240(5) Uani 1 1 d . . . . .
C35 C 0.1038(3) 1.1694(3) 0.0622(2) 0.0244(5) Uani 1 1 d . . . . .
C36 C 0.0724(3) 1.2227(3) 0.1847(3) 0.0310(5) Uani 1 1 d . . . . .
H36A H -0.035351 1.314478 0.170634 0.037 Uiso 1 1 calc R U . . .
H36B H 0.166089 1.247912 0.203364 0.037 Uiso 1 1 calc R U . . .
C37 C 0.0624(3) 1.0961(3) 0.3016(3) 0.0318(6) Uani 1 1 d . . . . .
H37A H 0.051459 1.124937 0.385572 0.038 Uiso 1 1 calc R U . . .
H37B H -0.039340 1.079601 0.286841 0.038 Uiso 1 1 calc R U . . .
C38 C 0.5661(3) 0.7242(3) -0.0076(2) 0.0255(5) Uani 1 1 d . . . . .
H38A H 0.677846 0.709097 0.024710 0.038 Uiso 1 1 calc R U . . .
H38B H 0.501230 0.831532 -0.054842 0.038 Uiso 1 1 calc R U . . .
H38C H 0.580888 0.663930 -0.069240 0.038 Uiso 1 1 calc R U . . .
O3 O 0.1774(2) 0.79738(19) 0.79114(18) 0.0287(4) Uani 1 1 d G . . . .
H3A H 0.210156 0.831822 0.712706 0.043 Uiso 1 1 d G U . . .
H3B H 0.223354 0.699603 0.806863 0.043 Uiso 1 1 d G U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.237(3) . ?
N1 C1 1.355(3) . ?
N1 C18 1.466(3) . ?
N1 C8 1.491(3) . ?
N2 C10 1.378(3) . ?
N2 C9 1.386(3) . ?
C1 C2 1.513(3) . ?
C2 C3 1.509(3) . ?
C3 C4 1.521(3) . ?
C3 C7 1.530(3) . ?
C4 C5 1.528(3) . ?
C5 C6 1.561(3) . ?
C6 C19 1.525(3) . ?
C6 C7 1.552(3) . ?
C7 C8 1.527(3) . ?
C8 C9 1.503(3) . ?
C9 C16 1.366(3) . ?
C10 C11 1.398(3) . ?
C10 C15 1.416(3) . ?
C11 C12 1.390(3) . ?
C12 C13 1.402(4) . ?
C13 C14 1.377(3) . ?
C14 C15 1.403(3) . ?
C15 C16 1.434(3) . ?
C16 C17 1.494(3) . ?
C17 C18 1.521(3) . ?
O2 C20 1.239(3) . ?
N3 C20 1.357(3) . ?
N3 C37 1.481(3) . ?
N3 C27 1.496(3) . ?
N4 C28 1.380(3) . ?
N4 C29 1.383(3) . ?
C20 C21 1.513(3) . ?
C21 C22 1.510(3) . ?
C22 C23 1.523(3) . ?
C22 C26 1.529(3) . ?
C23 C24 1.531(3) . ?
C24 C25 1.564(3) . ?
C25 C38 1.522(3) . ?
C25 C26 1.551(3) . ?
C26 C27 1.522(3) . ?
C27 C28 1.507(3) . ?
C28 C35 1.364(3) . ?
C29 C30 1.394(3) . ?
C29 C34 1.420(3) . ?
C30 C31 1.388(3) . ?
C31 C32 1.402(4) . ?
C32 C33 1.381(4) . ?
C33 C34 1.403(3) . ?
C34 C35 1.435(3) . ?
C35 C36 1.497(3) . ?
C36 C37 1.519(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
C1 N1 C18 117.60(18) . . ?
C1 N1 C8 125.96(18) . . ?
C18 N1 C8 115.73(17) . . ?
C10 N2 C9 108.35(18) . . ?
O1 C1 N1 121.3(2) . . ?
O1 C1 C2 119.9(2) . . ?
N1 C1 C2 118.81(19) . . ?
C3 C2 C1 112.34(19) . . ?
C2 C3 C4 118.75(19) . . ?
C2 C3 C7 110.45(18) . . ?
C4 C3 C7 102.93(17) . . ?
C3 C4 C5 101.63(19) . . ?
C4 C5 C6 106.11(19) . . ?
C19 C6 C7 114.25(19) . . ?
C19 C6 C5 110.3(2) . . ?
C7 C6 C5 104.30(19) . . ?
C8 C7 C3 107.09(17) . . ?
C8 C7 C6 118.13(18) . . ?
C3 C7 C6 104.54(17) . . ?
N1 C8 C9 107.15(17) . . ?
N1 C8 C7 109.77(17) . . ?
C9 C8 C7 116.09(17) . . ?
C16 C9 N2 109.81(19) . . ?
C16 C9 C8 126.9(2) . . ?
N2 C9 C8 123.21(19) . . ?
N2 C10 C11 129.7(2) . . ?
N2 C10 C15 108.10(19) . . ?
C11 C10 C15 122.2(2) . . ?
C12 C11 C10 116.9(2) . . ?
C11 C12 C13 121.7(2) . . ?
C14 C13 C12 121.0(2) . . ?
C13 C14 C15 119.2(2) . . ?
C14 C15 C10 118.9(2) . . ?
C14 C15 C16 134.5(2) . . ?
C10 C15 C16 106.47(19) . . ?
C9 C16 C15 107.3(2) . . ?
C9 C16 C17 121.3(2) . . ?
C15 C16 C17 131.1(2) . . ?
C16 C17 C18 107.49(19) . . ?
N1 C18 C17 110.45(19) . . ?
C20 N3 C37 118.1(2) . . ?
C20 N3 C27 125.3(2) . . ?
C37 N3 C27 115.75(18) . . ?
C28 N4 C29 108.79(18) . . ?
O2 C20 N3 121.9(2) . . ?
O2 C20 C21 119.1(2) . . ?
N3 C20 C21 119.0(2) . . ?
C22 C21 C20 112.58(19) . . ?
C21 C22 C23 119.7(2) . . ?
C21 C22 C26 109.68(19) . . ?
C23 C22 C26 102.48(18) . . ?
C22 C23 C24 100.84(18) . . ?
C23 C24 C25 105.52(18) . . ?
C38 C25 C26 113.45(18) . . ?
C38 C25 C24 111.02(18) . . ?
C26 C25 C24 104.10(17) . . ?
C27 C26 C22 108.51(17) . . ?
C27 C26 C25 117.62(17) . . ?
C22 C26 C25 104.68(18) . . ?
N3 C27 C28 107.83(18) . . ?
N3 C27 C26 109.58(17) . . ?
C28 C27 C26 116.48(18) . . ?
C35 C28 N4 109.7(2) . . ?
C35 C28 C27 126.8(2) . . ?
N4 C28 C27 123.2(2) . . ?
N4 C29 C30 129.8(2) . . ?
N4 C29 C34 107.57(19) . . ?
C30 C29 C34 122.6(2) . . ?
C31 C30 C29 116.8(2) . . ?
C30 C31 C32 121.6(2) . . ?
C33 C32 C31 121.2(2) . . ?
C32 C33 C34 119.0(2) . . ?
C33 C34 C29 118.7(2) . . ?
C33 C34 C35 134.7(2) . . ?
C29 C34 C35 106.5(2) . . ?
C28 C35 C34 107.4(2) . . ?
C28 C35 C36 121.1(2) . . ?
C34 C35 C36 131.0(2) . . ?
C35 C36 C37 107.8(2) . . ?
N3 C37 C36 110.2(2) . . ?

_refine_diff_density_max         0.266
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.050

