# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_SPA707
_database_code_depnum_ccdc_archive 'CCDC 2206957'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2022-09-13 deposited with the CCDC.	2022-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '6(C20 H16 N2 O2), H2 O'
_chemical_formula_sum            'C120 H98 N12 O13'
_chemical_formula_weight         1916.10

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0024 0.0013 '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 0.0048 0.0027 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0087 0.0050 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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'
'-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                   40.300(6)
_cell_length_b                   40.300(6)
_cell_length_c                   5.1760(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     7280(2)
_cell_formula_units_Z            3
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    68050
_cell_measurement_theta_min      0.372
_cell_measurement_theta_max      33.425

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             3018
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.101
_exptl_crystal_size_mid          0.048
_exptl_crystal_size_min          0.042
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.650
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20970
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_limit_h_min       -52
_diffrn_reflns_limit_h_max       52
_diffrn_reflns_limit_k_min       -52
_diffrn_reflns_limit_k_max       52
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         1.849
_diffrn_reflns_theta_max         24.988
_diffrn_reflns_theta_full        22.955
_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             3724
_reflns_number_gt                2816
_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       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_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)+(0.1113P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3724
_refine_ls_number_parameters     271
_refine_ls_number_restraints     63
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1826
_refine_ls_wR_factor_gt          0.1746
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_restrained_S_all      1.403
_refine_ls_shift/su_max          0.001
_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 0.58768(4) 0.89626(4) 0.9263(3) 0.0520(4) Uani 1 1 d . . . . .
H1 H 0.571632 0.888458 0.807983 0.078 Uiso 1 1 calc R U . . .
O2 O 0.39998(3) 0.73651(3) -0.3237(2) 0.0372(3) Uani 1 1 d . . . . .
H2O2 H 0.379402 0.736555 -0.323207 0.056 Uiso 1 1 calc R U . . .
N1 N 0.53025(4) 0.88903(4) 0.6729(3) 0.0337(3) Uani 1 1 d . . . . .
N2 N 0.49930(4) 0.86622(4) 0.5116(3) 0.0391(4) Uani 1 1 d . . . . .
C1 C 0.58669(5) 0.92499(5) 1.0536(3) 0.0346(4) Uani 1 1 d . . . . .
C2 C 0.61378(5) 0.94368(5) 1.2454(3) 0.0389(4) Uani 1 1 d . . . . .
H2 H 0.632142 0.936374 1.279886 0.047 Uiso 1 1 calc R U . . .
C3 C 0.61405(5) 0.97273(5) 1.3854(4) 0.0414(4) Uani 1 1 d . . . . .
H3 H 0.632481 0.985081 1.515620 0.050 Uiso 1 1 calc R U . . .
C4 C 0.58725(5) 0.98398(5) 1.3358(4) 0.0433(5) Uani 1 1 d . . . . .
H4 H 0.587768 1.004196 1.429738 0.052 Uiso 1 1 calc R U . . .
C5 C 0.55996(5) 0.96535(5) 1.1483(3) 0.0359(4) Uani 1 1 d . . . . .
H5 H 0.541917 0.973143 1.115964 0.043 Uiso 1 1 calc R U . . .
C6 C 0.55821(4) 0.93503(4) 1.0034(3) 0.0295(4) Uani 1 1 d . . . . .
C7 C 0.52722(5) 0.91369(5) 0.8159(3) 0.0320(4) Uani 1 1 d . . . . .
C8A C 0.49403(5) 0.92038(5) 0.8058(3) 0.0383(4) Uani 0.486(3) 1 d D . P A 1
C9A C 0.47115(8) 0.91507(9) 1.0429(6) 0.0304(8) Uani 0.486(3) 1 d D . P A 1
H9A H 0.478054 0.907623 1.196608 0.036 Uiso 0.486(3) 1 calc R U P A 1
C10A C 0.43966(9) 0.92079(10) 1.0451(7) 0.0365(8) Uani 0.486(3) 1 d D . P A 1
H10A H 0.426935 0.918742 1.201605 0.044 Uiso 0.486(3) 1 calc R U P A 1
C11A C 0.4268(2) 0.9295(2) 0.8176(12) 0.0411(15) Uani 0.486(3) 1 d D . P A 1
H11A H 0.406475 0.934642 0.819024 0.049 Uiso 0.486(3) 1 calc R U P A 1
C12A C 0.44557(10) 0.93033(11) 0.5879(8) 0.0428(10) Uani 0.486(3) 1 d D . P A 1
H12A H 0.437020 0.935159 0.430925 0.051 Uiso 0.486(3) 1 calc R U P A 1
C13A C 0.47655(9) 0.92412(10) 0.5868(6) 0.0358(8) Uani 0.486(3) 1 d D . P A 1
H13A H 0.486306 0.922356 0.425590 0.043 Uiso 0.486(3) 1 calc R U P A 1
C8B C 0.49403(5) 0.92038(5) 0.8058(3) 0.0383(4) Uani 0.514(3) 1 d D . P A 2
C9B C 0.50306(9) 0.95773(9) 0.7094(7) 0.0375(8) Uani 0.514(3) 1 d D . P A 2
H9B H 0.528057 0.976139 0.659839 0.045 Uiso 0.514(3) 1 calc R U P A 2
C10B C 0.47283(11) 0.96485(11) 0.6941(8) 0.0489(10) Uani 0.514(3) 1 d D . P A 2
H10B H 0.476726 0.988501 0.633125 0.059 Uiso 0.514(3) 1 calc R U P A 2
C11B C 0.43706(16) 0.9366(2) 0.7701(16) 0.055(2) Uani 0.514(3) 1 d D . P A 2
H11B H 0.416473 0.941335 0.766732 0.066 Uiso 0.514(3) 1 calc R U P A 2
C12B C 0.43101(10) 0.90180(13) 0.8501(10) 0.0603(12) Uani 0.514(3) 1 d D . P A
2
H12B H 0.406163 0.882556 0.895913 0.072 Uiso 0.514(3) 1 calc R U P A 2
C13B C 0.46081(9) 0.89456(11) 0.8647(8) 0.0463(10) Uani 0.514(3) 1 d D . P A 2
H13B H 0.456358 0.870390 0.918405 0.056 Uiso 0.514(3) 1 calc R U P A 2
C14 C 0.50726(5) 0.84746(4) 0.3501(3) 0.0322(4) Uani 1 1 d . . . . .
H14 H 0.532482 0.851921 0.343657 0.039 Uiso 1 1 calc R U . . .
C15 C 0.47890(5) 0.81933(5) 0.1745(3) 0.0300(4) Uani 1 1 d . . . . .
C16 C 0.44014(5) 0.80839(5) 0.1913(3) 0.0372(4) Uani 1 1 d . . . . .
H16 H 0.432075 0.819833 0.315902 0.045 Uiso 1 1 calc R U . . .
C17 C 0.41354(5) 0.78099(5) 0.0272(3) 0.0363(4) Uani 1 1 d . . . . .
H17 H 0.387524 0.773737 0.041028 0.044 Uiso 1 1 calc R U . . .
C18 C 0.42529(5) 0.76421(4) -0.1579(3) 0.0294(4) Uani 1 1 d . . . . .
C19 C 0.46358(5) 0.77458(5) -0.1783(3) 0.0340(4) Uani 1 1 d . . . . .
H19 H 0.471517 0.763199 -0.304093 0.041 Uiso 1 1 calc R U . . .
C20 C 0.49001(5) 0.80183(5) -0.0118(3) 0.0344(4) Uani 1 1 d . . . . .
H20 H 0.515928 0.808669 -0.024436 0.041 Uiso 1 1 calc R U . . .
O1W O 0.333333 0.666667 0.166667 0.251(6) Uani 1 6 d DS T P . .
H1OW H 0.333333 0.666667 0.344(2) 0.377 Uiso 0.5 3 d DS U P . .
H2OW H 0.326(9) 0.683(7) 0.101(7) 0.377 Uiso 0.1667 1 d D 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
O1 C1 1.350(2) . ?
O1 H1 0.8300 . ?
O2 C18 1.3726(19) . ?
O2 H2O2 0.8300 . ?
N1 C7 1.293(2) . ?
N1 N2 1.397(2) . ?
N2 C14 1.271(2) . ?
C1 C2 1.387(3) . ?
C1 C6 1.419(2) . ?
C2 C3 1.372(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.388(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.375(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.405(2) . ?
C5 H5 0.9400 . ?
C6 C7 1.472(2) . ?
C7 C8B 1.492(2) . ?
C7 C8A 1.492(2) . ?
C8A C13A 1.382(3) . ?
C8A C9A 1.485(3) . ?
C9A C10A 1.398(4) . ?
C9A H9A 0.9400 . ?
C10A C11A 1.400(6) . ?
C10A H10A 0.9400 . ?
C11A C12A 1.401(6) . ?
C11A H11A 0.9400 . ?
C12A C13A 1.390(4) . ?
C12A H12A 0.9400 . ?
C13A H13A 0.9400 . ?
C8B C13B 1.255(3) . ?
C8B C9B 1.449(3) . ?
C9B C10B 1.386(4) . ?
C9B H9B 0.9400 . ?
C10B C11B 1.374(6) . ?
C10B H10B 0.9400 . ?
C11B C12B 1.362(6) . ?
C11B H11B 0.9400 . ?
C12B C13B 1.373(4) . ?
C12B H12B 0.9400 . ?
C13B H13B 0.9400 . ?
C14 C15 1.456(2) . ?
C14 H14 0.9400 . ?
C15 C20 1.394(2) . ?
C15 C16 1.398(2) . ?
C16 C17 1.381(2) . ?
C16 H16 0.9400 . ?
C17 C18 1.386(2) . ?
C17 H17 0.9400 . ?
C18 C19 1.387(2) . ?
C19 C20 1.383(2) . ?
C19 H19 0.9400 . ?
C20 H20 0.9400 . ?
O1W H1OW 0.916(10) . ?
O1W H2OW 0.916(10) . ?

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 O1 H1 109.5 . . ?
C18 O2 H2O2 109.5 . . ?
C7 N1 N2 116.83(14) . . ?
C14 N2 N1 112.11(14) . . ?
O1 C1 C2 117.54(15) . . ?
O1 C1 C6 122.02(15) . . ?
C2 C1 C6 120.38(16) . . ?
C3 C2 C1 120.64(16) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.34(17) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.54(17) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 122.03(17) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C1 117.02(15) . . ?
C5 C6 C7 121.26(15) . . ?
C1 C6 C7 121.67(15) . . ?
N1 C7 C6 116.60(15) . . ?
N1 C7 C8B 123.83(15) . . ?
C6 C7 C8B 119.54(14) . . ?
N1 C7 C8A 123.83(15) . . ?
C6 C7 C8A 119.54(14) . . ?
C13A C8A C9A 112.3(2) . . ?
C13A C8A C7 126.9(2) . . ?
C9A C8A C7 119.56(17) . . ?
C10A C9A C8A 122.1(3) . . ?
C10A C9A H9A 118.9 . . ?
C8A C9A H9A 118.9 . . ?
C9A C10A C11A 121.0(4) . . ?
C9A C10A H10A 119.5 . . ?
C11A C10A H10A 119.5 . . ?
C10A C11A C12A 117.2(5) . . ?
C10A C11A H11A 121.4 . . ?
C12A C11A H11A 121.4 . . ?
C13A C12A C11A 121.5(4) . . ?
C13A C12A H12A 119.3 . . ?
C11A C12A H12A 119.3 . . ?
C8A C13A C12A 124.7(3) . . ?
C8A C13A H13A 117.7 . . ?
C12A C13A H13A 117.7 . . ?
C13B C8B C9B 123.7(2) . . ?
C13B C8B C7 121.5(2) . . ?
C9B C8B C7 114.68(19) . . ?
C10B C9B C8B 116.4(3) . . ?
C10B C9B H9B 121.8 . . ?
C8B C9B H9B 121.8 . . ?
C9B C10B C11B 118.6(4) . . ?
C9B C10B H10B 120.7 . . ?
C11B C10B H10B 120.7 . . ?
C12B C11B C10B 120.9(5) . . ?
C12B C11B H11B 119.5 . . ?
C10B C11B H11B 119.5 . . ?
C11B C12B C13B 120.7(4) . . ?
C11B C12B H12B 119.7 . . ?
C13B C12B H12B 119.7 . . ?
C8B C13B C12B 119.6(3) . . ?
C8B C13B H13B 120.2 . . ?
C12B C13B H13B 120.2 . . ?
N2 C14 C15 122.67(16) . . ?
N2 C14 H14 118.7 . . ?
C15 C14 H14 118.7 . . ?
C20 C15 C16 118.33(15) . . ?
C20 C15 C14 119.97(15) . . ?
C16 C15 C14 121.68(15) . . ?
C17 C16 C15 120.81(16) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 119.87(15) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
O2 C18 C17 122.21(14) . . ?
O2 C18 C19 117.41(14) . . ?
C17 C18 C19 120.37(15) . . ?
C20 C19 C18 119.42(15) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C15 121.20(15) . . ?
C19 C20 H20 119.4 . . ?
C15 C20 H20 119.4 . . ?
H1OW O1W H2OW 112(3) . . ?

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
C7 N1 N2 C14 169.40(15) . . . . ?
O1 C1 C2 C3 -178.95(17) . . . . ?
C6 C1 C2 C3 -1.5(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C1 -1.8(2) . . . . ?
C4 C5 C6 C7 175.77(16) . . . . ?
O1 C1 C6 C5 179.83(16) . . . . ?
C2 C1 C6 C5 2.5(2) . . . . ?
O1 C1 C6 C7 2.3(3) . . . . ?
C2 C1 C6 C7 -175.00(15) . . . . ?
N2 N1 C7 C6 174.28(14) . . . . ?
N2 N1 C7 C8B -3.7(2) . . . . ?
N2 N1 C7 C8A -3.7(2) . . . . ?
C5 C6 C7 N1 172.98(15) . . . . ?
C1 C6 C7 N1 -9.6(2) . . . . ?
C5 C6 C7 C8B -9.0(2) . . . . ?
C1 C6 C7 C8B 168.44(15) . . . . ?
C5 C6 C7 C8A -9.0(2) . . . . ?
C1 C6 C7 C8A 168.44(15) . . . . ?
N1 C7 C8A C13A -44.9(3) . . . . ?
C6 C7 C8A C13A 137.2(2) . . . . ?
N1 C7 C8A C9A 121.6(2) . . . . ?
C6 C7 C8A C9A -56.3(2) . . . . ?
C13A C8A C9A C10A -11.5(4) . . . . ?
C7 C8A C9A C10A -179.8(3) . . . . ?
C8A C9A C10A C11A 4.1(6) . . . . ?
C9A C10A C11A C12A 3.2(9) . . . . ?
C10A C11A C12A C13A -2.3(9) . . . . ?
C9A C8A C13A C12A 12.7(4) . . . . ?
C7 C8A C13A C12A 180.0(3) . . . . ?
C11A C12A C13A C8A -6.5(7) . . . . ?
N1 C7 C8B C13B 63.3(3) . . . . ?
C6 C7 C8B C13B -114.6(3) . . . . ?
N1 C7 C8B C9B -113.2(2) . . . . ?
C6 C7 C8B C9B 68.9(2) . . . . ?
C13B C8B C9B C10B 2.8(5) . . . . ?
C7 C8B C9B C10B 179.2(3) . . . . ?
C8B C9B C10B C11B 0.0(6) . . . . ?
C9B C10B C11B C12B -2.3(10) . . . . ?
C10B C11B C12B C13B 2.1(11) . . . . ?
C9B C8B C13B C12B -3.1(6) . . . . ?
C7 C8B C13B C12B -179.3(3) . . . . ?
C11B C12B C13B C8B 0.7(8) . . . . ?
N1 N2 C14 C15 174.98(14) . . . . ?
N2 C14 C15 C20 175.06(16) . . . . ?
N2 C14 C15 C16 -6.7(3) . . . . ?
C20 C15 C16 C17 -0.1(3) . . . . ?
C14 C15 C16 C17 -178.40(16) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C16 C17 C18 O2 179.19(15) . . . . ?
C16 C17 C18 C19 0.4(3) . . . . ?
O2 C18 C19 C20 -178.73(14) . . . . ?
C17 C18 C19 C20 0.1(2) . . . . ?
C18 C19 C20 C15 -0.6(3) . . . . ?
C16 C15 C20 C19 0.7(2) . . . . ?
C14 C15 C20 C19 178.96(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.83 1.82 2.547(2) 145.6 . yes
O2 H2O2 O2 0.83 1.93 2.7543(12) 175.3 15_554 yes

_refine_diff_density_max         0.802
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.055



# start Validation Reply Form
_vrf_PLAT420_SPA707              
;
PROBLEM: D-H Bond Without Acceptor  O1W      --H1OW     .     Please Check
RESPONSE: no available acceptors could be found at an acceptable distance
from the water hydrogens
;
# end Validation Reply Form



















####################################################################### 
# 
# 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_SPA711
_database_code_depnum_ccdc_archive 'CCDC 2206958'
loop_
_audit_author_name
_audit_author_address
'Dohyun Moon'
;Pohang Accelerator Laboratory
South Korea
;
_audit_update_record             
;
2022-09-13 deposited with the CCDC.	2022-12-06 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         'C20 H16 N2 O2'
_chemical_formula_sum            'C20 H16 N2 O2'
_chemical_formula_weight         316.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0021 0.0012 '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 0.0044 0.0025 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0080 0.0047 '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                   8.3490(17)
_cell_length_b                   16.722(3)
_cell_length_c                   11.913(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.15(3)
_cell_angle_gamma                90
_cell_volume                     1656.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    54663
_cell_measurement_theta_min      0.361
_cell_measurement_theta_max      33.548

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.062
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.057
_exptl_absorpt_coefficient_mu    0.065
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.920
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
'HKL3000sm Scalepack(Otwinowski et.al,2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.630
_diffrn_radiation_type           synchrotron
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_measurement_device_type  'Rayonix MX225HS CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15431
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.865
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        22.210
_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             4182
_reflns_number_gt                3730
_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       
'PAL BL2D-SMDC Program(Shin et.al, 2016)'
_computing_cell_refinement       'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_data_reduction        'HKL3000sm(Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2018(Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018(Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND 4(Putx&Brandenburg, 2014)'
_computing_publication_material  'publCIF(Westrip, 2010)'
_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)+(0.0856P)²+0.3546P] 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         4182
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1594
_refine_ls_wR_factor_gt          0.1563
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_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 0.33516(13) 0.26933(7) 0.48481(8) 0.0435(3) Uani 1 1 d . . . . .
H1 H 0.281074 0.276240 0.539151 0.065 Uiso 1 1 calc R U . . .
O2 O -0.02170(12) 0.63311(5) 0.66624(9) 0.0400(3) Uani 1 1 d . . . . .
H2O2 H -0.093844 0.646509 0.706023 0.060 Uiso 1 1 calc R U . . .
N1 N 0.26730(13) 0.19503(6) 0.71850(9) 0.0286(2) Uani 1 1 d . . . . .
N2 N 0.24420(13) 0.27529(6) 0.68654(9) 0.0304(2) Uani 1 1 d . . . . .
C1 C 0.48484(16) 0.24538(7) 0.52259(10) 0.0308(3) Uani 1 1 d . . . . .
C2 C 0.6121(2) 0.27121(8) 0.46289(12) 0.0412(3) Uani 1 1 d . . . . .
H2 H 0.590197 0.303845 0.399098 0.049 Uiso 1 1 calc R U . . .
C3 C 0.7677(2) 0.25001(10) 0.49533(14) 0.0482(4) Uani 1 1 d . . . . .
H3 H 0.851580 0.268582 0.454599 0.058 Uiso 1 1 calc R U . . .
C4 C 0.80134(19) 0.20107(11) 0.58842(14) 0.0495(4) Uani 1 1 d . . . . .
H4 H 0.908150 0.187031 0.611870 0.059 Uiso 1 1 calc R U . . .
C5 C 0.67645(17) 0.17303(9) 0.64656(12) 0.0391(3) Uani 1 1 d . . . . .
H5 H 0.699766 0.138520 0.708148 0.047 Uiso 1 1 calc R U . . .
C6 C 0.51667(15) 0.19459(7) 0.61627(9) 0.0277(3) Uani 1 1 d . . . . .
C7 C 0.39149(14) 0.15989(7) 0.68378(9) 0.0268(2) Uani 1 1 d . . . . .
C8 C 0.40938(16) 0.07472(7) 0.71908(10) 0.0301(3) Uani 1 1 d . . . . .
C9 C 0.4357(3) 0.01715(8) 0.63920(13) 0.0558(5) Uani 1 1 d . . . . .
H9 H 0.454066 0.032862 0.565684 0.067 Uiso 1 1 calc R U . . .
C10 C 0.4353(3) -0.06343(9) 0.66662(16) 0.0636(6) Uani 1 1 d . . . . .
H10 H 0.450010 -0.102103 0.611210 0.076 Uiso 1 1 calc R U . . .
C11 C 0.4132(2) -0.08692(8) 0.77535(14) 0.0476(4) Uani 1 1 d . . . . .
H11 H 0.413577 -0.141497 0.794245 0.057 Uiso 1 1 calc R U . . .
C12 C 0.39051(17) -0.02994(8) 0.85592(12) 0.0377(3) Uani 1 1 d . . . . .
H12 H 0.377298 -0.045834 0.930215 0.045 Uiso 1 1 calc R U . . .
C13 C 0.38701(15) 0.05069(7) 0.82840(10) 0.0305(3) Uani 1 1 d . . . . .
H13 H 0.369530 0.089092 0.883615 0.037 Uiso 1 1 calc R U . . .
C14 C 0.16794(15) 0.31679(7) 0.75490(11) 0.0318(3) Uani 1 1 d . . . . .
H14 H 0.138219 0.292542 0.821126 0.038 Uiso 1 1 calc R U . . .
C15 C 0.12593(15) 0.40004(7) 0.73342(11) 0.0318(3) Uani 1 1 d . . . . .
C16 C 0.16929(17) 0.44123(8) 0.63838(12) 0.0380(3) Uani 1 1 d . . . . .
H16 H 0.232053 0.415485 0.587549 0.046 Uiso 1 1 calc R U . . .
C17 C 0.12084(17) 0.51913(8) 0.61863(12) 0.0377(3) Uani 1 1 d . . . . .
H17 H 0.151213 0.546342 0.554830 0.045 Uiso 1 1 calc R U . . .
C18 C 0.02685(14) 0.55766(7) 0.69314(11) 0.0311(3) Uani 1 1 d . . . . .
C19 C -0.01222(17) 0.51868(8) 0.78998(11) 0.0353(3) Uani 1 1 d . . . . .
H19 H -0.071475 0.545332 0.842068 0.042 Uiso 1 1 calc R U . . .
C20 C 0.03663(17) 0.44025(8) 0.80943(11) 0.0356(3) Uani 1 1 d . . . . .
H20 H 0.009262 0.413813 0.874669 0.043 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 C1 1.3504(17) . ?
O1 H1 0.8300 . ?
O2 C18 1.3549(15) . ?
O2 H2O2 0.8300 . ?
N1 C7 1.2917(15) . ?
N1 N2 1.4038(13) . ?
N2 C14 1.2819(16) . ?
C1 C2 1.3987(19) . ?
C1 C6 1.4086(16) . ?
C2 C3 1.369(2) . ?
C2 H2 0.9400 . ?
C3 C4 1.386(2) . ?
C3 H3 0.9400 . ?
C4 C5 1.3844(19) . ?
C4 H4 0.9400 . ?
C5 C6 1.3976(19) . ?
C5 H5 0.9400 . ?
C6 C7 1.4923(16) . ?
C7 C8 1.4887(15) . ?
C8 C9 1.3850(17) . ?
C8 C13 1.3915(16) . ?
C9 C10 1.387(2) . ?
C9 H9 0.9400 . ?
C10 C11 1.382(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.377(2) . ?
C11 H11 0.9400 . ?
C12 C13 1.3872(17) . ?
C12 H12 0.9400 . ?
C13 H13 0.9400 . ?
C14 C15 1.4528(16) . ?
C14 H14 0.9400 . ?
C15 C20 1.3961(17) . ?
C15 C16 1.4004(18) . ?
C16 C17 1.3780(18) . ?
C16 H16 0.9400 . ?
C17 C18 1.3942(18) . ?
C17 H17 0.9400 . ?
C18 C19 1.3892(18) . ?
C19 C20 1.3866(18) . ?
C19 H19 0.9400 . ?
C20 H20 0.9400 . ?

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 O1 H1 109.5 . . ?
C18 O2 H2O2 109.5 . . ?
C7 N1 N2 116.28(9) . . ?
C14 N2 N1 114.15(10) . . ?
O1 C1 C2 117.46(11) . . ?
O1 C1 C6 123.09(12) . . ?
C2 C1 C6 119.42(12) . . ?
C3 C2 C1 121.43(13) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 119.86(13) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.50(14) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.86(13) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 117.90(11) . . ?
C5 C6 C7 117.32(11) . . ?
C1 C6 C7 124.75(11) . . ?
N1 C7 C8 114.06(10) . . ?
N1 C7 C6 128.09(10) . . ?
C8 C7 C6 117.84(10) . . ?
C9 C8 C13 119.03(11) . . ?
C9 C8 C7 119.27(11) . . ?
C13 C8 C7 121.48(10) . . ?
C8 C9 C10 120.64(13) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 120.03(14) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 119.67(13) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.58(12) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 120.01(12) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
N2 C14 C15 122.19(11) . . ?
N2 C14 H14 118.9 . . ?
C15 C14 H14 118.9 . . ?
C20 C15 C16 118.65(11) . . ?
C20 C15 C14 118.81(11) . . ?
C16 C15 C14 122.54(11) . . ?
C17 C16 C15 120.65(12) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 120.10(12) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
O2 C18 C19 123.08(11) . . ?
O2 C18 C17 116.95(11) . . ?
C19 C18 C17 119.97(11) . . ?
C20 C19 C18 119.67(11) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C15 120.88(12) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.6 . . ?

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
C7 N1 N2 C14 -152.74(12) . . . . ?
O1 C1 C2 C3 179.83(14) . . . . ?
C6 C1 C2 C3 -1.8(2) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C6 -2.0(3) . . . . ?
C4 C5 C6 C1 1.0(2) . . . . ?
C4 C5 C6 C7 179.13(14) . . . . ?
O1 C1 C6 C5 179.17(12) . . . . ?
C2 C1 C6 C5 0.92(18) . . . . ?
O1 C1 C6 C7 1.16(19) . . . . ?
C2 C1 C6 C7 -177.09(11) . . . . ?
N2 N1 C7 C8 -179.43(10) . . . . ?
N2 N1 C7 C6 1.83(18) . . . . ?
C5 C6 C7 N1 138.85(14) . . . . ?
C1 C6 C7 N1 -43.13(19) . . . . ?
C5 C6 C7 C8 -39.84(15) . . . . ?
C1 C6 C7 C8 138.18(12) . . . . ?
N1 C7 C8 C9 130.60(16) . . . . ?
C6 C7 C8 C9 -50.52(19) . . . . ?
N1 C7 C8 C13 -43.98(17) . . . . ?
C6 C7 C8 C13 134.90(13) . . . . ?
C13 C8 C9 C10 1.8(3) . . . . ?
C7 C8 C9 C10 -172.87(18) . . . . ?
C8 C9 C10 C11 -1.9(3) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
C10 C11 C12 C13 1.1(3) . . . . ?
C11 C12 C13 C8 -1.2(2) . . . . ?
C9 C8 C13 C12 -0.3(2) . . . . ?
C7 C8 C13 C12 174.29(12) . . . . ?
N1 N2 C14 C15 -177.05(11) . . . . ?
N2 C14 C15 C20 177.22(13) . . . . ?
N2 C14 C15 C16 -1.7(2) . . . . ?
C20 C15 C16 C17 -1.8(2) . . . . ?
C14 C15 C16 C17 177.09(13) . . . . ?
C15 C16 C17 C18 -0.4(2) . . . . ?
C16 C17 C18 O2 -177.49(13) . . . . ?
C16 C17 C18 C19 2.8(2) . . . . ?
O2 C18 C19 C20 177.44(13) . . . . ?
C17 C18 C19 C20 -2.9(2) . . . . ?
C18 C19 C20 C15 0.6(2) . . . . ?
C16 C15 C20 C19 1.8(2) . . . . ?
C14 C15 C20 C19 -177.21(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.83 2.54 3.1462(15) 130.5 . yes
O1 H1 N2 0.83 1.81 2.5865(15) 155.2 . yes
O2 H2O2 N1 0.83 1.95 2.7691(15) 169.5 2_556 yes

_refine_diff_density_max         0.388
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.058























