# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_yg333_2_0m_a_sq
_database_code_depnum_ccdc_archive 'CCDC 2128033'
loop_
_audit_author_name
_audit_author_address
'Yan-Ping Zhu'
;Yantai University
China
;
_audit_update_record             
;
2021-12-12 deposited with the CCDC.	2022-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C61 H38 Cl2 N12 O4'
_chemical_formula_weight         1073.93

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.021(3)
_cell_length_b                   36.936(6)
_cell_length_c                   8.7261(15)
_cell_angle_alpha                90
_cell_angle_beta                 94.790(3)
_cell_angle_gamma                90
_cell_volume                     5466.9(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2106
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      21.67

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             2216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.179
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17067
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.044
_diffrn_reflns_theta_max         27.531
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6261
_reflns_number_gt                3138
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6261
_refine_ls_number_parameters     366
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1272
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.2122
_refine_ls_wR_factor_gt          0.1766
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.53897(10) 0.58010(6) 0.6128(3) 0.2180(9) Uani 1 1 d . . . . .
O1 O 0.93644(11) 0.64671(7) 0.0523(3) 0.0925(7) Uani 1 1 d . . . . .
O2 O 0.93408(16) 0.70478(9) 0.1313(4) 0.0846(10) Uani 0.65 1 d . . P . .
O3 O 0.9147(4) 0.59016(19) 0.0136(10) 0.116(3) Uani 0.35 1 d . . P . .
N1 N 0.90121(13) 0.67583(7) 0.1314(3) 0.0701(7) Uani 1 1 d . . . . .
N2 N 0.89057(15) 0.61557(8) 0.0663(3) 0.0792(7) Uani 1 1 d . . . . .
N3 N 0.80394(15) 0.56757(6) 0.2488(3) 0.0709(7) Uani 1 1 d . . . . .
N4 N 0.64076(14) 0.58027(6) 0.2139(3) 0.0715(7) Uani 1 1 d . . . . .
N5 N 0.70606(10) 0.69259(5) 0.4812(2) 0.0463(5) Uani 1 1 d . . . . .
N6 N 0.76083(11) 0.71455(5) 0.2002(2) 0.0482(5) Uani 1 1 d . . . . .
C1 C 0.6708(2) 0.54984(8) 0.2844(3) 0.0741(8) Uani 1 1 d . . . . .
C2 C 0.7514(2) 0.54301(7) 0.2971(3) 0.0768(9) Uani 1 1 d . . . . .
C3 C 0.7807(3) 0.51035(9) 0.3647(4) 0.0976(11) Uani 1 1 d . . . . .
H3 H 0.834501 0.505466 0.372524 0.117 Uiso 1 1 calc R U . . .
C4 C 0.7298(3) 0.48648(11) 0.4175(5) 0.1207(15) Uani 1 1 d . U . . .
H4 H 0.748814 0.465037 0.462503 0.145 Uiso 1 1 calc R U . . .
C5 C 0.6496(4) 0.49329(11) 0.4060(5) 0.1251(15) Uani 1 1 d . U . . .
H5 H 0.615606 0.476343 0.443308 0.150 Uiso 1 1 calc R U . . .
C6 C 0.6199(3) 0.52418(10) 0.3413(4) 0.1083(13) Uani 1 1 d . . . . .
H6 H 0.565869 0.528383 0.334474 0.130 Uiso 1 1 calc R U . . .
C7 C 0.83784(13) 0.66177(7) 0.1872(3) 0.0521(6) Uani 1 1 d . . . . .
C8 C 0.83174(14) 0.62487(7) 0.1454(3) 0.0560(7) Uani 1 1 d . . . . .
C9 C 0.77355(15) 0.59765(7) 0.1859(3) 0.0563(7) Uani 1 1 d . . . . .
C10 C 0.69105(15) 0.60390(7) 0.1625(3) 0.0555(6) Uani 1 1 d . . . . .
C11 C 0.65702(14) 0.63625(7) 0.0798(3) 0.0526(6) Uani 1 1 d . . . . .
C12 C 0.59483(14) 0.65432(8) 0.1392(3) 0.0646(7) Uani 1 1 d . . . . .
H12 H 0.575466 0.646276 0.229706 0.078 Uiso 1 1 calc R U . . .
C13 C 0.56174(17) 0.68415(9) 0.0643(4) 0.0753(8) Uani 1 1 d . . . . .
H13 H 0.520351 0.696363 0.104549 0.090 Uiso 1 1 calc R U . . .
C14 C 0.59027(17) 0.69591(8) -0.0712(4) 0.0740(8) Uani 1 1 d . . . . .
H14 H 0.568383 0.716246 -0.121047 0.089 Uiso 1 1 calc R U . . .
C15 C 0.65110(16) 0.67760(8) -0.1329(3) 0.0658(7) Uani 1 1 d . . . . .
H15 H 0.669339 0.685164 -0.225180 0.079 Uiso 1 1 calc R U . . .
C16 C 0.68427(15) 0.64818(7) -0.0566(3) 0.0588(7) Uani 1 1 d . . . . .
H16 H 0.725719 0.636051 -0.097064 0.071 Uiso 1 1 calc R U . . .
C17 C 0.78558(12) 0.68476(6) 0.2724(3) 0.0450(6) Uani 1 1 d . . . . .
C18 C 0.76049(12) 0.67362(6) 0.4168(3) 0.0442(5) Uani 1 1 d . . . . .
C19 C 0.79148(14) 0.64132(6) 0.5001(3) 0.0496(6) Uani 1 1 d . . . . .
C20 C 0.87154(15) 0.63336(7) 0.5163(3) 0.0606(7) Uani 1 1 d . . . . .
H20 H 0.906933 0.648646 0.472708 0.073 Uiso 1 1 calc R U . . .
C21 C 0.89938(18) 0.60299(8) 0.5965(4) 0.0773(9) Uani 1 1 d . . . . .
H21 H 0.953121 0.598030 0.607849 0.093 Uiso 1 1 calc R U . . .
C22 C 0.8464(2) 0.58011(8) 0.6596(4) 0.0839(10) Uani 1 1 d . . . . .
H22 H 0.864508 0.559512 0.712726 0.101 Uiso 1 1 calc R U . . .
C23 C 0.7671(2) 0.58774(7) 0.6438(3) 0.0745(8) Uani 1 1 d . . . . .
H23 H 0.731894 0.572206 0.686409 0.089 Uiso 1 1 calc R U . . .
C24 C 0.73943(16) 0.61800(6) 0.5660(3) 0.0586(7) Uani 1 1 d . . . . .
H24 H 0.685690 0.622985 0.557134 0.070 Uiso 1 1 calc R U . . .
C25 C 0.67781(12) 0.72296(6) 0.4081(3) 0.0448(6) Uani 1 1 d . . . . .
C26 C 0.61877(14) 0.74339(7) 0.4722(3) 0.0554(6) Uani 1 1 d . . . . .
H26 H 0.599696 0.736221 0.564252 0.066 Uiso 1 1 calc R U . . .
C27 C 0.58982(15) 0.77362(7) 0.3987(3) 0.0618(7) Uani 1 1 d . . . . .
H27 H 0.550521 0.786918 0.440841 0.074 Uiso 1 1 calc R U . . .
C28 C 0.61833(16) 0.78509(7) 0.2603(3) 0.0649(7) Uani 1 1 d . . . . .
H28 H 0.597831 0.805916 0.212211 0.078 Uiso 1 1 calc R U . . .
C29 C 0.67527(15) 0.76621(7) 0.1959(3) 0.0583(7) Uani 1 1 d . . . . .
H29 H 0.693711 0.774019 0.104151 0.070 Uiso 1 1 calc R U . . .
C30 C 0.70654(13) 0.73459(6) 0.2688(3) 0.0463(6) Uani 1 1 d . . . . .
C31 C 0.500000 0.60433(18) 0.750000 0.176(4) Uani 1 2 d S T P . .
H01A H 0.459221 0.619861 0.701531 0.211 Uiso 0.5 1 calc R U P . .
H01B H 0.540780 0.619861 0.798468 0.211 Uiso 0.5 1 calc R U P . .


_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 C31 1.675(4) . ?
O1 N2 1.401(3) . ?
O1 N1 1.436(3) . ?
O2 N1 1.207(3) . ?
O3 N2 1.137(6) . ?
N1 C7 1.326(3) . ?
N2 C8 1.308(3) . ?
N3 C9 1.325(3) . ?
N3 C2 1.365(4) . ?
N4 C10 1.327(3) . ?
N4 C1 1.360(3) . ?
N5 C18 1.323(3) . ?
N5 C25 1.358(3) . ?
N6 C17 1.319(3) . ?
N6 C30 1.361(3) . ?
C1 C2 1.390(4) . ?
C1 C6 1.402(4) . ?
C2 C3 1.416(4) . ?
C3 C4 1.344(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.352(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.412(4) . ?
C7 C17 1.475(3) . ?
C8 C9 1.475(4) . ?
C9 C10 1.421(3) . ?
C10 C11 1.488(3) . ?
C11 C16 1.385(3) . ?
C11 C12 1.388(3) . ?
C12 C13 1.377(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.385(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.424(3) . ?
C18 C19 1.472(3) . ?
C19 C20 1.390(3) . ?
C19 C24 1.394(3) . ?
C20 C21 1.385(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.383(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.374(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.371(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.409(3) . ?
C25 C30 1.415(3) . ?
C26 C27 1.359(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.405(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.353(4) . ?
C28 H28 0.9300 . ?
C29 C30 1.412(3) . ?
C29 H29 0.9300 . ?
C31 H01A 0.9700 . ?
C31 H01B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 O1 N1 108.34(19) . . ?
O2 N1 C7 137.6(3) . . ?
O2 N1 O1 116.8(3) . . ?
C7 N1 O1 105.6(2) . . ?
O3 N2 C8 138.5(5) . . ?
O3 N2 O1 114.8(4) . . ?
C8 N2 O1 106.7(2) . . ?
C9 N3 C2 116.2(3) . . ?
C10 N4 C1 117.9(3) . . ?
C18 N5 C25 118.1(2) . . ?
C17 N6 C30 116.4(2) . . ?
N4 C1 C2 121.1(3) . . ?
N4 C1 C6 119.9(3) . . ?
C2 C1 C6 118.9(3) . . ?
N3 C2 C1 121.5(3) . . ?
N3 C2 C3 118.5(3) . . ?
C1 C2 C3 120.0(3) . . ?
C4 C3 C2 119.1(4) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 121.1(4) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 121.1(5) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 119.9(4) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
N1 C7 C8 109.1(2) . . ?
N1 C7 C17 120.2(2) . . ?
C8 C7 C17 130.6(2) . . ?
N2 C8 C7 110.3(2) . . ?
N2 C8 C9 120.4(2) . . ?
C7 C8 C9 129.2(2) . . ?
N3 C9 C10 122.9(3) . . ?
N3 C9 C8 115.1(2) . . ?
C10 C9 C8 122.0(2) . . ?
N4 C10 C9 120.1(2) . . ?
N4 C10 C11 117.2(2) . . ?
C9 C10 C11 122.7(2) . . ?
C16 C11 C12 119.2(2) . . ?
C16 C11 C10 121.8(2) . . ?
C12 C11 C10 118.9(2) . . ?
C13 C12 C11 120.1(3) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 119.8(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 119.3(3) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C11 121.0(2) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
N6 C17 C18 123.8(2) . . ?
N6 C17 C7 114.9(2) . . ?
C18 C17 C7 121.2(2) . . ?
N5 C18 C17 119.6(2) . . ?
N5 C18 C19 117.0(2) . . ?
C17 C18 C19 123.3(2) . . ?
C20 C19 C24 118.6(2) . . ?
C20 C19 C18 122.0(2) . . ?
C24 C19 C18 119.4(2) . . ?
C21 C20 C19 121.0(3) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C22 C21 C20 119.3(3) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C23 C22 C21 120.1(3) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C24 C23 C22 120.7(3) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C19 120.3(3) . . ?
C23 C24 H24 119.9 . . ?
C19 C24 H24 119.9 . . ?
N5 C25 C26 119.5(2) . . ?
N5 C25 C30 121.3(2) . . ?
C26 C25 C30 119.2(2) . . ?
C27 C26 C25 119.7(3) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C26 C27 C28 121.0(2) . . ?
C26 C27 H27 119.5 . . ?
C28 C27 H27 119.5 . . ?
C29 C28 C27 120.8(2) . . ?
C29 C28 H28 119.6 . . ?
C27 C28 H28 119.6 . . ?
C28 C29 C30 119.7(3) . . ?
C28 C29 H29 120.2 . . ?
C30 C29 H29 120.2 . . ?
N6 C30 C29 119.8(2) . . ?
N6 C30 C25 120.6(2) . . ?
C29 C30 C25 119.6(2) . . ?
Cl1 C31 Cl1 115.4(4) . 2_656 ?
Cl1 C31 H01A 108.4 . . ?
Cl1 C31 H01A 108.4 2_656 . ?
Cl1 C31 H01B 108.4 . . ?
Cl1 C31 H01B 108.4 2_656 . ?
H01A C31 H01B 107.5 . . ?

_refine_diff_density_max         0.216
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.043



####################################################################### 
# 
# 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_YG372_0m
_database_code_depnum_ccdc_archive 'CCDC 2141316'
loop_
_audit_author_name
_audit_author_address
'Yan-Ping Zhu'
;Yantai University
China
;
_audit_update_record             
;
2022-01-11 deposited with the CCDC.	2022-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H12 N4 O'
_chemical_formula_weight         324.34

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   5.866(2)
_cell_length_b                   9.372(3)
_cell_length_c                   28.177(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.035(5)
_cell_angle_gamma                90
_cell_volume                     1548.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1875
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      25.11

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9372
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1.446
_diffrn_reflns_theta_max         27.612
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3550
_reflns_number_gt                2289
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3550
_refine_ls_number_parameters     226
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1613
_refine_ls_wR_factor_gt          0.1348
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_restrained_S_all      0.946
_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 0.2188(3) 0.30445(16) 0.55840(5) 0.0672(4) Uani 1 1 d . U . . .
N1 N 0.3904(3) 0.57458(15) 0.66920(5) 0.0448(4) Uani 1 1 d . . . . .
N2 N 0.2340(3) 0.39550(18) 0.59870(5) 0.0563(5) Uani 1 1 d . U . . .
N3 N 0.5575(3) 0.41027(15) 0.55786(5) 0.0429(4) Uani 1 1 d . . . . .
N4 N 0.3062(3) 0.14153(15) 0.48051(5) 0.0423(4) Uani 1 1 d . . . . .
C1 C 0.3274(4) 0.6912(2) 0.74329(7) 0.0566(5) Uani 1 1 d . . . . .
H1 H 0.190560 0.642077 0.746050 0.068 Uiso 1 1 calc R U . . .
C2 C 0.3936(4) 0.7855(2) 0.77751(8) 0.0637(6) Uani 1 1 d . . . . .
H2 H 0.301004 0.800465 0.803496 0.076 Uiso 1 1 calc R U . . .
C3 C 0.5989(4) 0.8603(2) 0.77420(8) 0.0638(6) Uani 1 1 d . . . . .
H3 H 0.640511 0.925378 0.797726 0.077 Uiso 1 1 calc R U . . .
C4 C 0.7376(4) 0.8387(2) 0.73698(7) 0.0583(5) Uani 1 1 d . . . . .
H4 H 0.874623 0.888248 0.735445 0.070 Uiso 1 1 calc R U . . .
C5 C 0.6768(3) 0.74143(18) 0.70027(6) 0.0449(4) Uani 1 1 d . . . . .
C6 C 0.4661(3) 0.66767(18) 0.70347(6) 0.0429(4) Uani 1 1 d . . . . .
C7 C 0.5240(3) 0.55284(17) 0.63234(6) 0.0401(4) Uani 1 1 d . . . . .
C8 C 0.7391(3) 0.6183(2) 0.62668(6) 0.0470(5) Uani 1 1 d . . . . .
H8 H 0.827752 0.598279 0.600475 0.056 Uiso 1 1 calc R U . . .
C9 C 0.8125(3) 0.7114(2) 0.66072(7) 0.0506(5) Uani 1 1 d . . . . .
H9 H 0.953476 0.755659 0.657857 0.061 Uiso 1 1 calc R U . . .
C10 C 0.4371(3) 0.45295(18) 0.59584(6) 0.0425(4) Uani 1 1 d . . . . .
C11 C 0.4171(3) 0.31957(18) 0.53684(6) 0.0426(4) Uani 1 1 d . U . . .
C12 C 0.4639(3) 0.23427(18) 0.49412(6) 0.0413(4) Uani 1 1 d . . . . .
C13 C 0.6755(3) 0.25348(19) 0.47156(6) 0.0446(4) Uani 1 1 d . . . . .
H13 H 0.783399 0.317329 0.483522 0.054 Uiso 1 1 calc R U . . .
C14 C 0.7158(3) 0.17580(19) 0.43192(7) 0.0476(5) Uani 1 1 d . . . . .
H14 H 0.851783 0.187895 0.415925 0.057 Uiso 1 1 calc R U . . .
C15 C 0.5529(3) 0.07697(18) 0.41489(6) 0.0418(4) Uani 1 1 d . . . . .
C16 C 0.3492(3) 0.06050(17) 0.44105(6) 0.0399(4) Uani 1 1 d . . . . .
C17 C 0.1862(3) -0.04161(19) 0.42676(7) 0.0485(5) Uani 1 1 d . . . . .
H17 H 0.055935 -0.055206 0.444548 0.058 Uiso 1 1 calc R U . . .
C18 C 0.2193(4) -0.1212(2) 0.38656(7) 0.0556(5) Uani 1 1 d . . . . .
H18 H 0.110748 -0.188263 0.377120 0.067 Uiso 1 1 calc R U . . .
C19 C 0.4163(4) -0.1021(2) 0.35956(7) 0.0589(6) Uani 1 1 d . . . . .
H19 H 0.434683 -0.154889 0.331949 0.071 Uiso 1 1 calc R U . . .
C20 C 0.5805(4) -0.0072(2) 0.37334(7) 0.0539(5) Uani 1 1 d . . . . .
H20 H 0.711373 0.002641 0.355487 0.065 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 C11 1.330(2) . ?
O1 N2 1.4219(19) . ?
N1 C7 1.328(2) . ?
N1 C6 1.369(2) . ?
N2 C10 1.311(2) . ?
N3 C11 1.317(2) . ?
N3 C10 1.353(2) . ?
N4 C12 1.321(2) . ?
N4 C16 1.374(2) . ?
C1 C2 1.360(3) . ?
C1 C6 1.415(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.398(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.354(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.419(3) . ?
C4 H4 0.9300 . ?
C5 C9 1.409(3) . ?
C5 C6 1.420(3) . ?
C7 C8 1.414(3) . ?
C7 C10 1.475(2) . ?
C8 C9 1.361(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C11 C12 1.475(2) . ?
C12 C13 1.416(3) . ?
C13 C14 1.358(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.409(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.423(2) . ?
C15 C20 1.423(2) . ?
C16 C17 1.407(3) . ?
C17 C18 1.373(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.406(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.362(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 N2 104.95(14) . . ?
C7 N1 C6 117.43(16) . . ?
C10 N2 O1 103.98(13) . . ?
C11 N3 C10 102.44(15) . . ?
C12 N4 C16 117.45(15) . . ?
C2 C1 C6 120.2(2) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C1 C2 C3 120.9(2) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.9(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C9 C5 C4 124.50(19) . . ?
C9 C5 C6 117.22(17) . . ?
C4 C5 C6 118.28(18) . . ?
N1 C6 C1 118.35(17) . . ?
N1 C6 C5 122.46(16) . . ?
C1 C6 C5 119.19(17) . . ?
N1 C7 C8 124.19(17) . . ?
N1 C7 C10 116.17(16) . . ?
C8 C7 C10 119.64(16) . . ?
C9 C8 C7 118.04(17) . . ?
C9 C8 H8 121.0 . . ?
C7 C8 H8 121.0 . . ?
C8 C9 C5 120.62(18) . . ?
C8 C9 H9 119.7 . . ?
C5 C9 H9 119.7 . . ?
N2 C10 N3 114.52(16) . . ?
N2 C10 C7 121.41(16) . . ?
N3 C10 C7 124.06(17) . . ?
N3 C11 O1 114.11(15) . . ?
N3 C11 C12 126.39(16) . . ?
O1 C11 C12 119.48(16) . . ?
N4 C12 C13 124.60(16) . . ?
N4 C12 C11 117.02(16) . . ?
C13 C12 C11 118.34(16) . . ?
C14 C13 C12 117.93(17) . . ?
C14 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
C13 C14 C15 120.37(17) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C16 117.73(15) . . ?
C14 C15 C20 123.93(17) . . ?
C16 C15 C20 118.35(17) . . ?
N4 C16 C17 118.29(16) . . ?
N4 C16 C15 121.83(16) . . ?
C17 C16 C15 119.88(16) . . ?
C18 C17 C16 120.01(18) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.45(19) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 120.84(18) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C15 120.39(19) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 O1 N2 C10 0.3(2) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C3 C4 C5 C9 -179.13(19) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C7 N1 C6 C1 -179.35(16) . . . . ?
C7 N1 C6 C5 1.1(2) . . . . ?
C2 C1 C6 N1 -178.34(18) . . . . ?
C2 C1 C6 C5 1.3(3) . . . . ?
C9 C5 C6 N1 -2.3(3) . . . . ?
C4 C5 C6 N1 178.31(16) . . . . ?
C9 C5 C6 C1 178.13(17) . . . . ?
C4 C5 C6 C1 -1.3(3) . . . . ?
C6 N1 C7 C8 0.7(3) . . . . ?
C6 N1 C7 C10 -179.52(14) . . . . ?
N1 C7 C8 C9 -1.2(3) . . . . ?
C10 C7 C8 C9 179.07(16) . . . . ?
C7 C8 C9 C5 -0.2(3) . . . . ?
C4 C5 C9 C8 -178.86(18) . . . . ?
C6 C5 C9 C8 1.8(3) . . . . ?
O1 N2 C10 N3 0.3(2) . . . . ?
O1 N2 C10 C7 -178.23(15) . . . . ?
C11 N3 C10 N2 -0.7(2) . . . . ?
C11 N3 C10 C7 177.76(15) . . . . ?
N1 C7 C10 N2 3.5(2) . . . . ?
C8 C7 C10 N2 -176.70(17) . . . . ?
N1 C7 C10 N3 -174.86(16) . . . . ?
C8 C7 C10 N3 4.9(3) . . . . ?
C10 N3 C11 O1 0.9(2) . . . . ?
C10 N3 C11 C12 -177.12(16) . . . . ?
N2 O1 C11 N3 -0.8(2) . . . . ?
N2 O1 C11 C12 177.41(15) . . . . ?
C16 N4 C12 C13 -1.5(3) . . . . ?
C16 N4 C12 C11 -179.32(14) . . . . ?
N3 C11 C12 N4 175.25(16) . . . . ?
O1 C11 C12 N4 -2.7(2) . . . . ?
N3 C11 C12 C13 -2.7(3) . . . . ?
O1 C11 C12 C13 179.36(16) . . . . ?
N4 C12 C13 C14 3.0(3) . . . . ?
C11 C12 C13 C14 -179.20(16) . . . . ?
C12 C13 C14 C15 -1.5(3) . . . . ?
C13 C14 C15 C16 -1.1(3) . . . . ?
C13 C14 C15 C20 179.15(17) . . . . ?
C12 N4 C16 C17 178.28(15) . . . . ?
C12 N4 C16 C15 -1.4(2) . . . . ?
C14 C15 C16 N4 2.6(2) . . . . ?
C20 C15 C16 N4 -177.56(15) . . . . ?
C14 C15 C16 C17 -177.01(16) . . . . ?
C20 C15 C16 C17 2.8(2) . . . . ?
N4 C16 C17 C18 177.74(16) . . . . ?
C15 C16 C17 C18 -2.6(3) . . . . ?
C16 C17 C18 C19 0.4(3) . . . . ?
C17 C18 C19 C20 1.7(3) . . . . ?
C18 C19 C20 C15 -1.5(3) . . . . ?
C14 C15 C20 C19 179.02(18) . . . . ?
C16 C15 C20 C19 -0.8(3) . . . . ?

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.041

