# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_exp_11355
_database_code_depnum_ccdc_archive 'CCDC 2057762'
loop_
_audit_author_name
_audit_author_address
HFZG
;Qingdao Agricultural University
China
;
_audit_update_record             
;
2021-01-21 deposited with the CCDC.	2021-06-02 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            'C48 H55 N4 O2'
_chemical_formula_weight         719.96

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           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.9297(10)
_cell_length_b                   12.9240(9)
_cell_length_c                   13.666(2)
_cell_angle_alpha                75.136(9)
_cell_angle_beta                 78.644(10)
_cell_angle_gamma                89.902(6)
_cell_volume                     1994.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2319
_cell_measurement_theta_min      3.7950
_cell_measurement_theta_max      69.1790

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_F_000             774
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.567
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_T_min  0.90149
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13345
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.417
_diffrn_reflns_theta_max         67.235
_diffrn_reflns_theta_full        67.235
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             7100
_reflns_number_gt                3517
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7100
_refine_ls_number_parameters     487
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1753
_refine_ls_R_factor_gt           0.1157
_refine_ls_wR_factor_ref         0.3647
_refine_ls_wR_factor_gt          0.2884
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1049(4) 0.3037(3) 1.2288(3) 0.0677(11) Uani 1 1 d . . . . .
N2 N 0.3734(3) 0.3245(3) 0.7783(3) 0.0667(11) Uani 1 1 d . . . . .
N3 N 0.2865(4) 0.8051(3) 1.2333(3) 0.0671(11) Uani 1 1 d . . . . .
N4 N 0.2316(3) 0.8273(3) 0.7802(3) 0.0660(10) Uani 1 1 d . . . . .
O1 O 0.4141(4) 0.1371(3) 1.0695(3) 0.0929(12) Uani 1 1 d . . . . .
O2 O 0.0517(4) 0.6436(3) 1.0688(3) 0.0912(12) Uani 1 1 d . . . . .
C1 C 0.4586(4) 0.4040(4) 0.7514(4) 0.0597(11) Uani 1 1 d . . . . .
C2 C 0.4889(4) 0.4705(4) 0.6522(4) 0.0711(13) Uani 1 1 d . . . . .
H2 H 0.449182 0.462880 0.602153 0.085 Uiso 1 1 calc R U . . .
C3 C 0.5772(5) 0.5483(4) 0.6262(5) 0.0814(15) Uani 1 1 d . . . . .
H3 H 0.597154 0.591692 0.558968 0.098 Uiso 1 1 calc R U . . .
C4 C 0.6351(5) 0.5609(4) 0.7004(5) 0.0803(15) Uani 1 1 d . . . . .
H4 H 0.694611 0.612826 0.683549 0.096 Uiso 1 1 calc R U . . .
C5 C 0.6046(4) 0.4962(4) 0.8001(5) 0.0752(14) Uani 1 1 d . . . . .
H5 H 0.643922 0.505850 0.849782 0.090 Uiso 1 1 calc R U . . .
C6 C 0.5170(4) 0.4173(4) 0.8281(4) 0.0596(11) Uani 1 1 d . . . . .
C7 C 0.4863(4) 0.3495(4) 0.9369(4) 0.0642(12) Uani 1 1 d . . . . .
H7A H 0.494928 0.392911 0.983530 0.077 Uiso 1 1 calc R U . . .
H7B H 0.539089 0.292330 0.946308 0.077 Uiso 1 1 calc R U . . .
C8 C 0.3622(4) 0.2999(3) 0.9655(4) 0.0629(12) Uani 1 1 d . . . . .
C9 C 0.3508(4) 0.2474(4) 0.8783(4) 0.0669(13) Uani 1 1 d . . . . .
H9 H 0.407143 0.192246 0.877195 0.080 Uiso 1 1 calc R U . . .
C10 C 0.2343(5) 0.1967(4) 0.8839(4) 0.0770(15) Uani 1 1 d . . . . .
H10A H 0.224170 0.124353 0.928731 0.092 Uiso 1 1 calc R U . . .
H10B H 0.172845 0.239091 0.907885 0.092 Uiso 1 1 calc R U . . .
C11 C 0.2400(5) 0.1971(4) 0.7724(5) 0.0838(16) Uani 1 1 d . . . . .
H11A H 0.164126 0.188454 0.759097 0.101 Uiso 1 1 calc R U . . .
H11B H 0.286301 0.140349 0.754370 0.101 Uiso 1 1 calc R U . . .
C12 C 0.2960(4) 0.3081(4) 0.7118(5) 0.0764(14) Uani 1 1 d D . . . .
H12 H 0.340377 0.304556 0.644347 0.092 Uiso 1 1 calc R U . . .
C13 C 0.2106(5) 0.3959(5) 0.6974(5) 0.0872(17) Uani 1 1 d D . . . .
H13A H 0.158464 0.390874 0.762790 0.105 Uiso 1 1 calc R U . . .
H13B H 0.251314 0.465484 0.675941 0.105 Uiso 1 1 calc R U . . .
C14 C 0.1431(7) 0.3860(7) 0.6174(7) 0.117(2) Uani 1 1 d D . . . .
H14 H 0.090630 0.327916 0.634405 0.140 Uiso 1 1 calc R U . . .
C15 C 0.1528(9) 0.4539(8) 0.5244(8) 0.163(4) Uani 1 1 d D . . . .
H15A H 0.204408 0.513001 0.504517 0.196 Uiso 1 1 calc R U . . .
H15B H 0.108101 0.442285 0.479320 0.196 Uiso 1 1 calc R U . . .
C16 C 0.2796(4) 0.3864(3) 0.9703(4) 0.0616(12) Uani 1 1 d . . . . .
H16 H 0.283946 0.443207 0.911677 0.074 Uiso 1 1 calc R U . . .
C17 C 0.2008(4) 0.3867(3) 1.0529(4) 0.0621(12) Uani 1 1 d . . . . .
H17 H 0.153054 0.443865 1.051212 0.075 Uiso 1 1 calc R U . . .
C18 C 0.1873(4) 0.2998(4) 1.1462(4) 0.0627(12) Uani 1 1 d . . . . .
C19 C 0.2594(5) 0.2160(4) 1.1498(4) 0.0701(13) Uani 1 1 d . . . . .
H19 H 0.249413 0.160508 1.210032 0.084 Uiso 1 1 calc R U . . .
C20 C 0.3477(5) 0.2111(4) 1.0657(4) 0.0720(14) Uani 1 1 d . . . . .
C21 C 0.0882(5) 0.2215(4) 1.3261(4) 0.0746(14) Uani 1 1 d . . . . .
H21A H 0.158379 0.212951 1.352374 0.089 Uiso 1 1 calc R U . . .
H21B H 0.064362 0.153348 1.317247 0.089 Uiso 1 1 calc R U . . .
C22 C -0.0039(6) 0.2599(5) 1.3988(5) 0.0977(19) Uani 1 1 d . . . . .
H22A H -0.055229 0.200718 1.442726 0.117 Uiso 1 1 calc R U . . .
H22B H 0.028985 0.295148 1.442085 0.117 Uiso 1 1 calc R U . . .
C23 C -0.0649(6) 0.3367(6) 1.3290(5) 0.106(2) Uani 1 1 d . . . . .
H23A H -0.100069 0.389715 1.362611 0.127 Uiso 1 1 calc R U . . .
H23B H -0.124161 0.299324 1.309740 0.127 Uiso 1 1 calc R U . . .
C24 C 0.0261(5) 0.3903(4) 1.2335(5) 0.0826(16) Uani 1 1 d . . . . .
H24A H -0.006264 0.411124 1.171932 0.099 Uiso 1 1 calc R U . . .
H24B H 0.063469 0.452691 1.242827 0.099 Uiso 1 1 calc R U . . .
C25 C 0.1574(4) 0.9060(3) 0.7487(4) 0.0575(11) Uani 1 1 d . . . . .
C26 C 0.1701(5) 0.9679(4) 0.6480(4) 0.0719(13) Uani 1 1 d . . . . .
H26 H 0.231996 0.958041 0.598633 0.086 Uiso 1 1 calc R U . . .
C27 C 0.0943(6) 1.0428(4) 0.6192(5) 0.0851(16) Uani 1 1 d . . . . .
H27 H 0.103585 1.081561 0.550346 0.102 Uiso 1 1 calc R U . . .
C28 C 0.0026(5) 1.0620(4) 0.6924(5) 0.0829(16) Uani 1 1 d . . . . .
H28 H -0.048457 1.114152 0.673357 0.099 Uiso 1 1 calc R U . . .
C29 C -0.0105(4) 1.0021(4) 0.7930(5) 0.0721(14) Uani 1 1 d . . . . .
H29 H -0.071654 1.014240 0.841862 0.087 Uiso 1 1 calc R U . . .
C30 C 0.0650(4) 0.9236(3) 0.8244(4) 0.0593(11) Uani 1 1 d . . . . .
C31 C 0.0447(4) 0.8578(4) 0.9334(4) 0.0626(12) Uani 1 1 d . . . . .
H31A H -0.013987 0.802098 0.943137 0.075 Uiso 1 1 calc R U . . .
H31B H 0.015911 0.902917 0.978614 0.075 Uiso 1 1 calc R U . . .
C32 C 0.1540(4) 0.8043(4) 0.9659(4) 0.0599(11) Uani 1 1 d . . . . .
C33 C 0.2040(4) 0.7504(3) 0.8802(4) 0.0622(12) Uani 1 1 d . . . . .
H33 H 0.146729 0.697407 0.877610 0.075 Uiso 1 1 calc R U . . .
C34 C 0.3165(5) 0.6962(4) 0.8865(5) 0.0766(15) Uani 1 1 d . . . . .
H34A H 0.368387 0.737348 0.910253 0.092 Uiso 1 1 calc R U . . .
H34B H 0.304239 0.624272 0.932068 0.092 Uiso 1 1 calc R U . . .
C35 C 0.3617(5) 0.6941(4) 0.7754(5) 0.0835(16) Uani 1 1 d . . . . .
H35A H 0.323450 0.636789 0.758473 0.100 Uiso 1 1 calc R U . . .
H35B H 0.443460 0.684750 0.762897 0.100 Uiso 1 1 calc R U . . .
C36 C 0.3344(4) 0.8033(4) 0.7127(5) 0.0744(14) Uani 1 1 d D . . . .
H36 H 0.316413 0.797542 0.647237 0.089 Uiso 1 1 calc R U . . .
C37 C 0.4295(5) 0.8879(5) 0.6926(5) 0.0917(18) Uani 1 1 d D . . . .
H37A H 0.398771 0.958513 0.678734 0.110 Uiso 1 1 calc R U . . .
H37B H 0.463248 0.878035 0.753160 0.110 Uiso 1 1 calc R U . . .
C38 C 0.5197(8) 0.8792(7) 0.6009(8) 0.156(4) Uani 1 1 d D . . . .
H38 H 0.490505 0.895227 0.540791 0.187 Uiso 1 1 calc R U . . .
C39 C 0.6273(11) 0.8555(10) 0.5816(13) 0.245(8) Uani 1 1 d D . . . .
H39A H 0.667409 0.837795 0.635009 0.294 Uiso 1 1 calc R U . . .
H39B H 0.663529 0.856505 0.514585 0.294 Uiso 1 1 calc R U . . .
C40 C 0.2370(4) 0.8882(3) 0.9719(4) 0.0611(12) Uani 1 1 d . . . . .
H40 H 0.262213 0.943836 0.912902 0.073 Uiso 1 1 calc R U . . .
C41 C 0.2764(4) 0.8882(3) 1.0553(4) 0.0612(12) Uani 1 1 d . . . . .
H41 H 0.326566 0.943753 1.054068 0.073 Uiso 1 1 calc R U . . .
C42 C 0.2422(4) 0.8014(4) 1.1505(4) 0.0616(12) Uani 1 1 d . . . . .
C43 C 0.1699(5) 0.7196(4) 1.1518(4) 0.0681(13) Uani 1 1 d . . . . .
H43 H 0.152624 0.663187 1.211311 0.082 Uiso 1 1 calc R U . . .
C44 C 0.1194(4) 0.7162(4) 1.0665(4) 0.0683(13) Uani 1 1 d . . . . .
C45 C 0.3632(6) 0.8910(5) 1.2385(5) 0.0866(17) Uani 1 1 d . . . . .
H45A H 0.324231 0.957290 1.235672 0.104 Uiso 1 1 calc R U . . .
H45B H 0.430045 0.903355 1.182730 0.104 Uiso 1 1 calc R U . . .
C46 C 0.3949(11) 0.8485(8) 1.3398(7) 0.186(6) Uani 1 1 d . . . . .
H46A H 0.471201 0.821882 1.329862 0.224 Uiso 1 1 calc R U . . .
H46B H 0.395654 0.905697 1.373918 0.224 Uiso 1 1 calc R U . . .
C47 C 0.3154(7) 0.7639(6) 1.4037(5) 0.105(2) Uani 1 1 d . . . . .
H47 H 0.302637 0.738782 1.475285 0.127 Uiso 1 1 calc R U . . .
C48 C 0.2565(5) 0.7233(4) 1.3319(4) 0.0769(14) Uani 1 1 d . . . . .
H48A H 0.283867 0.654406 1.324767 0.092 Uiso 1 1 calc R U . . .
H48B H 0.174231 0.716133 1.357081 0.092 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C18 1.355(6) . ?
N1 C21 1.451(6) . ?
N1 C24 1.467(6) . ?
N2 C1 1.374(6) . ?
N2 C9 1.446(6) . ?
N2 C12 1.468(6) . ?
N3 C42 1.350(6) . ?
N3 C48 1.464(6) . ?
N3 C45 1.464(7) . ?
N4 C25 1.388(5) . ?
N4 C33 1.445(6) . ?
N4 C36 1.467(7) . ?
O1 C20 1.238(6) . ?
O2 C44 1.230(6) . ?
C1 C2 1.385(7) . ?
C1 C6 1.412(6) . ?
C2 C3 1.385(7) . ?
C3 C4 1.377(8) . ?
C4 C5 1.381(8) . ?
C5 C6 1.388(7) . ?
C6 C7 1.493(7) . ?
C7 C8 1.550(7) . ?
C8 C16 1.495(6) . ?
C8 C20 1.524(7) . ?
C8 C9 1.542(7) . ?
C9 C10 1.518(7) . ?
C10 C11 1.511(8) . ?
C11 C12 1.538(7) . ?
C12 C13 1.525(6) . ?
C13 C14 1.510(7) . ?
C14 C15 1.329(8) . ?
C16 C17 1.321(7) . ?
C17 C18 1.448(6) . ?
C18 C19 1.379(7) . ?
C19 C20 1.412(8) . ?
C21 C22 1.504(8) . ?
C22 C23 1.488(9) . ?
C23 C24 1.530(8) . ?
C25 C26 1.382(7) . ?
C25 C30 1.416(7) . ?
C26 C27 1.361(7) . ?
C27 C28 1.398(9) . ?
C28 C29 1.372(8) . ?
C29 C30 1.397(6) . ?
C30 C31 1.487(7) . ?
C31 C32 1.564(6) . ?
C32 C40 1.498(6) . ?
C32 C44 1.527(7) . ?
C32 C33 1.534(7) . ?
C33 C34 1.520(7) . ?
C34 C35 1.514(8) . ?
C35 C36 1.523(7) . ?
C36 C37 1.512(6) . ?
C37 C38 1.511(8) . ?
C38 C39 1.310(9) . ?
C40 C41 1.317(6) . ?
C41 C42 1.470(7) . ?
C42 C43 1.360(7) . ?
C43 C44 1.424(7) . ?
C45 C46 1.475(9) . ?
C46 C47 1.430(11) . ?
C47 C48 1.506(8) . ?

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
C18 N1 C21 122.4(4) . . ?
C18 N1 C24 125.5(4) . . ?
C21 N1 C24 112.0(4) . . ?
C1 N2 C9 122.1(4) . . ?
C1 N2 C12 125.1(4) . . ?
C9 N2 C12 112.8(4) . . ?
C42 N3 C48 122.2(4) . . ?
C42 N3 C45 125.7(4) . . ?
C48 N3 C45 112.1(4) . . ?
C25 N4 C33 121.6(4) . . ?
C25 N4 C36 124.4(4) . . ?
C33 N4 C36 113.4(4) . . ?
N2 C1 C2 122.3(4) . . ?
N2 C1 C6 118.3(4) . . ?
C2 C1 C6 119.4(4) . . ?
C1 C2 C3 121.3(5) . . ?
C4 C3 C2 119.6(5) . . ?
C3 C4 C5 119.8(5) . . ?
C4 C5 C6 121.8(5) . . ?
C5 C6 C1 118.2(5) . . ?
C5 C6 C7 120.1(4) . . ?
C1 C6 C7 121.7(4) . . ?
C6 C7 C8 112.7(4) . . ?
C16 C8 C20 113.7(4) . . ?
C16 C8 C9 110.9(4) . . ?
C20 C8 C9 107.7(4) . . ?
C16 C8 C7 109.5(4) . . ?
C20 C8 C7 109.2(4) . . ?
C9 C8 C7 105.5(4) . . ?
N2 C9 C10 103.4(4) . . ?
N2 C9 C8 111.7(4) . . ?
C10 C9 C8 116.8(4) . . ?
C11 C10 C9 101.5(4) . . ?
C10 C11 C12 103.5(4) . . ?
N2 C12 C13 112.1(4) . . ?
N2 C12 C11 100.9(4) . . ?
C13 C12 C11 113.5(5) . . ?
C14 C13 C12 111.1(5) . . ?
C15 C14 C13 125.1(8) . . ?
C17 C16 C8 123.7(4) . . ?
C16 C17 C18 121.2(4) . . ?
N1 C18 C19 121.4(5) . . ?
N1 C18 C17 119.0(4) . . ?
C19 C18 C17 119.6(5) . . ?
C18 C19 C20 122.6(5) . . ?
O1 C20 C19 122.8(5) . . ?
O1 C20 C8 118.1(5) . . ?
C19 C20 C8 119.1(4) . . ?
N1 C21 C22 105.6(5) . . ?
C23 C22 C21 103.9(5) . . ?
C22 C23 C24 105.9(6) . . ?
N1 C24 C23 101.2(5) . . ?
C26 C25 N4 123.2(4) . . ?
C26 C25 C30 118.9(4) . . ?
N4 C25 C30 117.8(4) . . ?
C27 C26 C25 121.8(5) . . ?
C26 C27 C28 120.4(6) . . ?
C29 C28 C27 118.6(5) . . ?
C28 C29 C30 122.2(5) . . ?
C29 C30 C25 118.1(5) . . ?
C29 C30 C31 120.2(5) . . ?
C25 C30 C31 121.6(4) . . ?
C30 C31 C32 113.6(4) . . ?
C40 C32 C44 113.5(4) . . ?
C40 C32 C33 110.9(4) . . ?
C44 C32 C33 107.7(4) . . ?
C40 C32 C31 109.8(4) . . ?
C44 C32 C31 109.6(4) . . ?
C33 C32 C31 104.9(4) . . ?
N4 C33 C34 102.0(4) . . ?
N4 C33 C32 111.5(3) . . ?
C34 C33 C32 117.6(4) . . ?
C35 C34 C33 102.3(4) . . ?
C34 C35 C36 103.9(4) . . ?
N4 C36 C37 111.0(4) . . ?
N4 C36 C35 101.8(4) . . ?
C37 C36 C35 112.9(5) . . ?
C38 C37 C36 109.5(6) . . ?
C39 C38 C37 138.4(13) . . ?
C41 C40 C32 124.1(4) . . ?
C40 C41 C42 120.8(4) . . ?
N3 C42 C43 122.4(5) . . ?
N3 C42 C41 118.1(4) . . ?
C43 C42 C41 119.5(4) . . ?
C42 C43 C44 123.1(5) . . ?
O2 C44 C43 123.1(5) . . ?
O2 C44 C32 118.1(4) . . ?
C43 C44 C32 118.8(4) . . ?
N3 C45 C46 102.7(5) . . ?
C47 C46 C45 110.7(7) . . ?
C46 C47 C48 106.4(6) . . ?
N3 C48 C47 104.4(5) . . ?

_refine_diff_density_max         0.612
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.087

####################################################################### 
# 
# 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_exp_11352
_database_code_depnum_ccdc_archive 'CCDC 2057763'
loop_
_audit_author_name
_audit_author_address
HFZK
;Qingdao Agricultural University
China
;
_audit_update_record             
;
2021-01-21 deposited with the CCDC.	2021-06-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H34 N2 O2'
_chemical_formula_weight         394.54

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   34.3408(11)
_cell_length_b                   34.3408(11)
_cell_length_c                   10.4316(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     10653.8(6)
_cell_formula_units_Z            18
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3852
_exptl_absorpt_coefficient_mu    0.545
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9375
_exptl_absorpt_correction_T_max  0.9425
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23249
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         67.19
_reflns_number_total             4238
_reflns_number_gt                2624
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1434P)²+3.4873P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00032(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4238
_refine_ls_number_parameters     287
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0732
_refine_ls_wR_factor_ref         0.2539
_refine_ls_wR_factor_gt          0.2217
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.092
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.21730(12) 0.07572(13) 0.4729(4) 0.1297(15) Uani 1 1 d D . .
N2 N 0.15166(8) -0.08724(8) -0.0270(2) 0.0755(7) Uani 1 1 d . . .
O1 O 0.14845(7) -0.05725(8) 0.2201(2) 0.0901(8) Uani 1 1 d . . .
H1 H 0.1526 -0.0670 0.1528 0.135 Uiso 1 1 calc R . .
O2 O 0.30987(9) 0.04359(10) -0.2616(2) 0.1060(9) Uani 1 1 d . A .
C1 C 0.22103(11) 0.04723(11) 0.3894(3) 0.0813(9) Uani 1 1 d . A .
C2 C 0.18365(10) 0.00838(11) 0.3435(3) 0.0768(9) Uani 1 1 d . . .
H2 H 0.1551 0.0013 0.3715 0.092 Uiso 1 1 calc R A .
C3 C 0.18784(10) -0.01982(9) 0.2575(2) 0.0670(7) Uani 1 1 d . A .
C4 C 0.22927(9) -0.01160(9) 0.2132(2) 0.0620(7) Uani 1 1 d . . .
C5 C 0.26606(10) 0.02713(10) 0.2586(3) 0.0732(8) Uani 1 1 d . A .
H5 H 0.2945 0.0341 0.2300 0.088 Uiso 1 1 calc R . .
C6 C 0.26296(11) 0.05592(11) 0.3438(3) 0.0822(9) Uani 1 1 d . . .
H6 H 0.2889 0.0814 0.3714 0.099 Uiso 1 1 calc R A .
C7 C 0.23432(11) -0.04338(10) 0.1241(3) 0.0693(7) Uani 1 1 d . A .
H7A H 0.2107 -0.0739 0.1423 0.083 Uiso 1 1 calc R . .
H7B H 0.2629 -0.0417 0.1409 0.083 Uiso 1 1 calc R . .
C8 C 0.23209(10) -0.03334(9) -0.0171(3) 0.0643(7) Uani 1 1 d . . .
C9 C 0.27181(10) -0.00167(10) -0.0749(3) 0.0707(8) Uani 1 1 d . A .
H9 H 0.2986 0.0106 -0.0289 0.085 Uiso 1 1 calc R . .
C10 C 0.27224(11) 0.01192(11) -0.1997(3) 0.0786(9) Uani 1 1 d . . .
C11 C 0.23254(12) -0.00659(12) -0.2686(3) 0.0855(10) Uani 1 1 d . A .
H11 H 0.2324 0.0028 -0.3521 0.103 Uiso 1 1 calc R . .
C12 C 0.19331(12) -0.03899(11) -0.2128(3) 0.0809(9) Uani 1 1 d . . .
H12 H 0.1669 -0.0519 -0.2604 0.097 Uiso 1 1 calc R A .
C13 C 0.19217(10) -0.05286(9) -0.0870(3) 0.0673(7) Uani 1 1 d . A .
C14 C 0.14755(14) -0.13268(11) -0.0288(4) 0.1009(12) Uani 1 1 d . . .
H14A H 0.1691 -0.1337 0.0292 0.121 Uiso 1 1 calc R . .
H14B H 0.1527 -0.1402 -0.1145 0.121 Uiso 1 1 calc R . .
C15 C 0.10049(16) -0.16453(14) 0.0137(4) 0.1208(16) Uani 1 1 d . . .
H15A H 0.0998 -0.1721 0.1036 0.145 Uiso 1 1 calc R . .
H15B H 0.0874 -0.1920 -0.0365 0.145 Uiso 1 1 calc R . .
C16 C 0.07516(13) -0.13893(14) -0.0085(4) 0.1093(14) Uani 1 1 d . . .
H16A H 0.0484 -0.1566 -0.0599 0.131 Uiso 1 1 calc R . .
H16B H 0.0663 -0.1317 0.0724 0.131 Uiso 1 1 calc R . .
C17 C 0.10837(11) -0.09621(12) -0.0792(3) 0.0868(10) Uani 1 1 d . . .
H17 H 0.1073 -0.1027 -0.1710 0.104 Uiso 1 1 calc R . .
C18 C 0.10138(13) -0.05605(14) -0.0599(4) 0.1007(11) Uani 1 1 d . . .
H18A H 0.1008 -0.0506 0.0311 0.121 Uiso 1 1 calc R . .
H18B H 0.1264 -0.0295 -0.0977 0.121 Uiso 1 1 calc R . .
C19 C 0.0586(2) -0.0640(2) -0.1195(6) 0.158(2) Uani 1 1 d D . .
H19 H 0.0363 -0.0940 -0.1140 0.189 Uiso 1 1 calc R . .
C20 C 0.0452(3) -0.0415(3) -0.1737(11) 0.265(5) Uani 1 1 d D . .
H20A H 0.0643 -0.0108 -0.1854 0.318 Uiso 1 1 calc R . .
H20B H 0.0157 -0.0550 -0.2033 0.318 Uiso 1 1 calc R . .
C21 C 0.1727(2) 0.0704(2) 0.5087(6) 0.161(2) Uani 1 1 d D A .
H21A H 0.1762 0.0995 0.5306 0.194 Uiso 1 1 calc R . .
H21B H 0.1522 0.0583 0.4367 0.194 Uiso 1 1 calc R . .
C22 C 0.1549(3) 0.0409(2) 0.6153(7) 0.197(3) Uani 1 1 d D . .
H22A H 0.1519 0.0123 0.5936 0.296 Uiso 1 1 calc R A .
H22B H 0.1259 0.0368 0.6371 0.296 Uiso 1 1 calc R . .
H22C H 0.1748 0.0535 0.6871 0.296 Uiso 1 1 calc R . .
C23 C 0.2531(3) 0.1245(3) 0.4839(9) 0.109(4) Uani 0.516(13) 1 d PD A 1
H23A H 0.2399 0.1432 0.5008 0.130 Uiso 0.516(13) 1 calc PR A 1
H23B H 0.2708 0.1349 0.4060 0.130 Uiso 0.516(13) 1 calc PR A 1
C24 C 0.2814(4) 0.1253(5) 0.5957(9) 0.131(4) Uani 0.516(13) 1 d PD A 1
H24A H 0.2655 0.1220 0.6743 0.196 Uiso 0.516(13) 1 calc PR A 1
H24B H 0.3092 0.1533 0.5965 0.196 Uiso 0.516(13) 1 calc PR A 1
H24C H 0.2875 0.1010 0.5874 0.196 Uiso 0.516(13) 1 calc PR A 1
C23' C 0.2563(3) 0.1062(2) 0.5583(9) 0.088(3) Uani 0.484(13) 1 d PD A 2
H23C H 0.2459 0.1067 0.6444 0.105 Uiso 0.484(13) 1 calc PR A 2
H23D H 0.2781 0.0961 0.5623 0.105 Uiso 0.484(13) 1 calc PR A 2
C24' C 0.2768(4) 0.1521(3) 0.4980(12) 0.121(4) Uani 0.484(13) 1 d PD A 2
H24D H 0.2900 0.1519 0.4171 0.182 Uiso 0.484(13) 1 calc PR A 2
H24E H 0.2996 0.1739 0.5537 0.182 Uiso 0.484(13) 1 calc PR A 2
H24F H 0.2539 0.1600 0.4848 0.182 Uiso 0.484(13) 1 calc PR A 2
C25 C 0.35033(13) 0.06602(16) -0.1867(4) 0.1147(14) Uani 1 1 d . . .
H25A H 0.3450 0.0790 -0.1119 0.172 Uiso 1 1 calc R A .
H25B H 0.3738 0.0894 -0.2371 0.172 Uiso 1 1 calc R . .
H25C H 0.3592 0.0447 -0.1612 0.172 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
N1 C1 1.363(4) . ?
N1 C21 1.497(7) . ?
N1 C23 1.507(8) . ?
N1 C23' 1.510(8) . ?
N2 C13 1.442(4) . ?
N2 C17 1.464(4) . ?
N2 C14 1.495(4) . ?
O1 C3 1.377(3) . ?
O2 C10 1.365(4) . ?
O2 C25 1.436(5) . ?
C1 C2 1.395(4) . ?
C1 C6 1.400(4) . ?
C2 C3 1.379(4) . ?
C3 C4 1.384(4) . ?
C4 C5 1.382(4) . ?
C4 C7 1.508(4) . ?
C5 C6 1.372(4) . ?
C7 C8 1.524(4) . ?
C8 C9 1.387(4) . ?
C8 C13 1.394(4) . ?
C9 C10 1.381(4) . ?
C10 C11 1.383(5) . ?
C11 C12 1.376(5) . ?
C12 C13 1.389(4) . ?
C14 C15 1.496(6) . ?
C15 C16 1.532(6) . ?
C16 C17 1.524(5) . ?
C17 C18 1.527(5) . ?
C18 C19 1.488(7) . ?
C19 C20 1.220(7) . ?
C21 C22 1.421(7) . ?
C23 C24 1.511(9) . ?
C23' C24' 1.506(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
C1 N1 C21 122.0(3) . . ?
C1 N1 C23 122.0(5) . . ?
C21 N1 C23 109.4(5) . . ?
C1 N1 C23' 120.4(4) . . ?
C21 N1 C23' 115.8(4) . . ?
C23 N1 C23' 40.3(4) . . ?
C13 N2 C17 118.3(3) . . ?
C13 N2 C14 113.5(3) . . ?
C17 N2 C14 102.7(3) . . ?
C10 O2 C25 116.5(3) . . ?
N1 C1 C2 122.3(3) . . ?
N1 C1 C6 121.4(3) . . ?
C2 C1 C6 116.3(3) . . ?
C3 C2 C1 121.7(3) . . ?
O1 C3 C2 116.2(3) . . ?
O1 C3 C4 121.7(3) . . ?
C2 C3 C4 122.1(3) . . ?
C5 C4 C3 115.7(3) . . ?
C5 C4 C7 121.8(3) . . ?
C3 C4 C7 122.4(2) . . ?
C6 C5 C4 123.5(3) . . ?
C5 C6 C1 120.6(3) . . ?
C4 C7 C8 113.3(2) . . ?
C9 C8 C13 119.7(3) . . ?
C9 C8 C7 117.2(3) . . ?
C13 C8 C7 123.1(3) . . ?
C10 C9 C8 121.0(3) . . ?
O2 C10 C9 124.1(3) . . ?
O2 C10 C11 116.3(3) . . ?
C9 C10 C11 119.6(3) . . ?
C12 C11 C10 119.6(3) . . ?
C11 C12 C13 121.7(3) . . ?
C12 C13 C8 118.5(3) . . ?
C12 C13 N2 122.7(3) . . ?
C8 C13 N2 118.8(2) . . ?
N2 C14 C15 105.3(3) . . ?
C14 C15 C16 104.5(3) . . ?
C17 C16 C15 105.0(3) . . ?
N2 C17 C16 102.4(3) . . ?
N2 C17 C18 111.3(3) . . ?
C16 C17 C18 115.2(3) . . ?
C19 C18 C17 111.5(4) . . ?
C20 C19 C18 136.8(8) . . ?
C22 C21 N1 109.2(7) . . ?
N1 C23 C24 103.7(9) . . ?
C24' C23' N1 105.6(9) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        67.19
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_exp_11901
_database_code_depnum_ccdc_archive 'CCDC 2061370'
loop_
_audit_author_name
_audit_author_address
r
;Qingdao Agricultural University
China
;
_audit_update_record             
;
2021-02-05 deposited with the CCDC.	2021-06-02 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            'C21 H25 Cl N2 O'
_chemical_formula_weight         356.88

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   15.3242(6)
_cell_length_b                   13.8242(5)
_cell_length_c                   9.0303(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.165(4)
_cell_angle_gamma                90
_cell_volume                     1854.85(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3203
_cell_measurement_theta_min      4.3770
_cell_measurement_theta_max      71.1270

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    1.896
_shelx_estimated_absorpt_T_min   0.670
_shelx_estimated_absorpt_T_max   0.692
_exptl_absorpt_correction_T_min  0.77418
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6379
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.368
_diffrn_reflns_theta_max         67.243
_diffrn_reflns_theta_full        67.243
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3327
_reflns_number_gt                2732
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0497P)²+0.3443P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0041(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3327
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1108
_refine_ls_wR_factor_gt          0.1046
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.61942(4) -0.13112(4) 0.04322(7) 0.0629(2) Uani 1 1 d . . . . .
N1 N 0.36457(11) -0.12132(12) 0.43797(17) 0.0508(4) Uani 1 1 d . . . . .
N2 N 0.08713(10) 0.21055(11) 0.25897(17) 0.0425(4) Uani 1 1 d . . . . .
O1 O 0.11102(9) -0.11610(9) 0.12212(17) 0.0549(4) Uani 1 1 d . . . . .
C1 C 0.54415(13) -0.12922(13) 0.1603(2) 0.0467(5) Uani 1 1 d . . . . .
C2 C 0.57412(14) -0.14826(15) 0.3139(3) 0.0541(5) Uani 1 1 d . . . . .
H2 H 0.634376 -0.162988 0.355270 0.065 Uiso 1 1 calc R U . . .
C3 C 0.51478(14) -0.14547(14) 0.4062(2) 0.0512(5) Uani 1 1 d . . . . .
H3 H 0.535668 -0.157519 0.510201 0.061 Uiso 1 1 calc R U . . .
C4 C 0.42355(13) -0.12482(13) 0.3463(2) 0.0423(4) Uani 1 1 d . . . . .
C5 C 0.39299(12) -0.10630(12) 0.1877(2) 0.0398(4) Uani 1 1 d . . . . .
C6 C 0.45431(13) -0.10838(13) 0.0982(2) 0.0445(4) Uani 1 1 d . . . . .
H6 H 0.434849 -0.095529 -0.005728 0.053 Uiso 1 1 calc R U . . .
C7 C 0.29507(12) -0.08425(14) 0.11958(19) 0.0421(4) Uani 1 1 d . . . . .
H7A H 0.263929 -0.143732 0.081745 0.051 Uiso 1 1 calc R U . . .
H7B H 0.290104 -0.040879 0.033466 0.051 Uiso 1 1 calc R U . . .
C8 C 0.24915(11) -0.03766(12) 0.23535(19) 0.0367(4) Uani 1 1 d . . . . .
C9 C 0.26852(12) -0.10539(13) 0.3773(2) 0.0432(4) Uani 1 1 d . . . . .
H9 H 0.239932 -0.168030 0.346171 0.052 Uiso 1 1 calc R U . . .
C10 C 0.23758(15) -0.06976(17) 0.5151(2) 0.0580(5) Uani 1 1 d . . . . .
H10A H 0.240944 0.000204 0.522506 0.070 Uiso 1 1 calc R U . . .
H10B H 0.176244 -0.089952 0.509624 0.070 Uiso 1 1 calc R U . . .
C11 C 0.30262(18) -0.11658(19) 0.6495(3) 0.0678(6) Uani 1 1 d . . . . .
H11A H 0.309078 -0.077544 0.740777 0.081 Uiso 1 1 calc R U . . .
H11B H 0.281816 -0.180500 0.668939 0.081 Uiso 1 1 calc R U . . .
C12 C 0.39089(15) -0.12283(15) 0.6034(2) 0.0538(5) Uani 1 1 d . . . . .
H12A H 0.429297 -0.068204 0.642832 0.065 Uiso 1 1 calc R U . . .
H12B H 0.422483 -0.182199 0.640524 0.065 Uiso 1 1 calc R U . . .
C13 C 0.28544(12) 0.06153(13) 0.2779(2) 0.0419(4) Uani 1 1 d . . . . .
H13 H 0.347548 0.069838 0.302487 0.050 Uiso 1 1 calc R U . . .
C14 C 0.23478(12) 0.13803(13) 0.2827(2) 0.0420(4) Uani 1 1 d . . . . .
H14 H 0.262234 0.197195 0.313172 0.050 Uiso 1 1 calc R U . . .
C15 C 0.13592(12) 0.13207(12) 0.24118(19) 0.0372(4) Uani 1 1 d . . . . .
C16 C 0.09693(11) 0.04627(13) 0.1806(2) 0.0403(4) Uani 1 1 d . . . . .
H16 H 0.034750 0.044164 0.143354 0.048 Uiso 1 1 calc R U . . .
C17 C 0.14701(11) -0.03861(13) 0.17228(19) 0.0386(4) Uani 1 1 d . . . . .
C18 C -0.01108(12) 0.20897(14) 0.2064(2) 0.0477(5) Uani 1 1 d . . . . .
H18A H -0.027774 0.177017 0.107904 0.057 Uiso 1 1 calc R U . . .
H18B H -0.032975 0.274994 0.192517 0.057 Uiso 1 1 calc R U . . .
C19 C -0.05666(16) 0.15787(18) 0.3153(3) 0.0670(6) Uani 1 1 d . . . . .
H19A H -0.032360 0.093850 0.335369 0.101 Uiso 1 1 calc R U . . .
H19B H -0.120170 0.153896 0.270397 0.101 Uiso 1 1 calc R U . . .
H19C H -0.046364 0.193435 0.409335 0.101 Uiso 1 1 calc R U . . .
C20 C 0.12512(14) 0.29796(14) 0.3420(2) 0.0543(5) Uani 1 1 d . . . . .
H20A H 0.182184 0.281948 0.411748 0.065 Uiso 1 1 calc R U . . .
H20B H 0.084825 0.320682 0.402251 0.065 Uiso 1 1 calc R U . . .
C21 C 0.1397(2) 0.37778(17) 0.2377(4) 0.0879(9) Uani 1 1 d . . . . .
H21A H 0.181575 0.356718 0.180905 0.132 Uiso 1 1 calc R U . . .
H21B H 0.163322 0.433644 0.297290 0.132 Uiso 1 1 calc R U . . .
H21C H 0.083419 0.394007 0.168342 0.132 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 C1 1.745(2) . ?
N1 C4 1.368(2) . ?
N1 C12 1.449(2) . ?
N1 C9 1.456(2) . ?
N2 C15 1.349(2) . ?
N2 C18 1.463(2) . ?
N2 C20 1.465(2) . ?
O1 C17 1.239(2) . ?
C1 C2 1.375(3) . ?
C1 C6 1.384(3) . ?
C2 C3 1.376(3) . ?
C3 C4 1.400(3) . ?
C4 C5 1.417(3) . ?
C5 C6 1.381(3) . ?
C5 C7 1.507(2) . ?
C7 C8 1.537(2) . ?
C8 C13 1.494(2) . ?
C8 C17 1.529(2) . ?
C8 C9 1.556(2) . ?
C9 C10 1.519(3) . ?
C10 C11 1.514(3) . ?
C11 C12 1.512(3) . ?
C13 C14 1.319(3) . ?
C14 C15 1.471(2) . ?
C15 C16 1.380(2) . ?
C16 C17 1.414(2) . ?
C18 C19 1.513(3) . ?
C20 C21 1.502(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
C4 N1 C12 124.41(17) . . ?
C4 N1 C9 122.29(15) . . ?
C12 N1 C9 113.01(16) . . ?
C15 N2 C18 120.35(15) . . ?
C15 N2 C20 124.17(15) . . ?
C18 N2 C20 115.25(15) . . ?
C2 C1 C6 120.13(18) . . ?
C2 C1 Cl1 120.06(16) . . ?
C6 C1 Cl1 119.81(16) . . ?
C1 C2 C3 119.89(19) . . ?
C2 C3 C4 121.13(19) . . ?
N1 C4 C3 121.24(17) . . ?
N1 C4 C5 120.10(16) . . ?
C3 C4 C5 118.65(18) . . ?
C6 C5 C4 118.91(17) . . ?
C6 C5 C7 121.18(16) . . ?
C4 C5 C7 119.91(16) . . ?
C5 C6 C1 121.29(18) . . ?
C5 C7 C8 112.53(14) . . ?
C13 C8 C17 112.73(14) . . ?
C13 C8 C7 110.85(15) . . ?
C17 C8 C7 109.90(14) . . ?
C13 C8 C9 110.88(14) . . ?
C17 C8 C9 105.85(14) . . ?
C7 C8 C9 106.33(14) . . ?
N1 C9 C10 103.30(15) . . ?
N1 C9 C8 111.88(15) . . ?
C10 C9 C8 116.43(16) . . ?
C11 C10 C9 104.00(17) . . ?
C12 C11 C10 105.18(17) . . ?
N1 C12 C11 103.93(17) . . ?
C14 C13 C8 124.01(16) . . ?
C13 C14 C15 121.63(16) . . ?
N2 C15 C16 122.67(16) . . ?
N2 C15 C14 119.38(15) . . ?
C16 C15 C14 117.92(16) . . ?
C15 C16 C17 123.12(16) . . ?
O1 C17 C16 122.55(16) . . ?
O1 C17 C8 117.85(16) . . ?
C16 C17 C8 119.50(15) . . ?
N2 C18 C19 113.45(17) . . ?
N2 C20 C21 112.74(19) . . ?

_refine_diff_density_max         0.182
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.036

