# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1900762'
loop_
_audit_author_name
_audit_author_address
'Haruki Sugiyama'
;Keio University
Japan
;
_audit_update_record             
;
2019-03-04 deposited with the CCDC.	2019-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 N3 O5'
_chemical_formula_sum            'C21 H21 N3 O5'
_chemical_formula_weight         395.41

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      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                   13.7790(3)
_cell_length_b                   6.80670(10)
_cell_length_c                   42.0629(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.2200(10)
_cell_angle_gamma                90
_cell_volume                     3913.78(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    18762
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      68.19

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             1664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.805
_shelx_estimated_absorpt_T_min   0.788
_shelx_estimated_absorpt_T_max   0.849
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.725
_exptl_absorpt_correction_T_max  0.849
_exptl_absorpt_process_details   'Absorption was corrected by ABSCOR'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID-II IP Area Detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21537
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_theta_min         4.238
_diffrn_reflns_theta_max         68.193
_diffrn_reflns_theta_full        67.686
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3584
_reflns_number_gt                2916
_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       'PROCESS-AUTO (Rigaku, 1998)'
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  'SHELXL-2018/8 (Sheldrick, 2018)'
_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)+(0.0762P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00056(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3584
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1245
_refine_ls_wR_factor_gt          0.1206
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_restrained_S_all      1.147
_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 0.88591(9) 0.81801(17) 0.77150(3) 0.0594(3) Uani 1 1 d . . . . .
H1A H 0.8931(15) 0.898(3) 0.7540(5) 0.089 Uiso 1 1 d . U . . .
O2 O 0.98845(9) 1.16052(17) 0.60027(2) 0.0635(3) Uani 1 1 d . . . . .
O3 O 0.92722(9) 0.90437(16) 0.62385(2) 0.0568(3) Uani 1 1 d . . . . .
H3A H 0.925547 0.856827 0.605875 0.085 Uiso 1 1 calc R U . . .
N1 N 0.88467(8) 1.12960(18) 0.73480(2) 0.0418(3) Uani 1 1 d . . . . .
C1 C 0.82684(10) 1.1344(2) 0.78607(3) 0.0414(3) Uani 1 1 d . . . . .
C2 C 0.84775(10) 0.9359(2) 0.79279(3) 0.0451(4) Uani 1 1 d . . . . .
C3 C 0.82909(11) 0.8567(3) 0.82198(4) 0.0556(4) Uani 1 1 d . . . . .
H3 H 0.842008 0.724702 0.826418 0.067 Uiso 1 1 calc R U . . .
C4 C 0.79163(11) 0.9731(3) 0.84421(3) 0.0602(5) Uani 1 1 d . . . . .
H4 H 0.779996 0.919067 0.863684 0.072 Uiso 1 1 calc R U . . .
C5 C 0.77099(12) 1.1694(3) 0.83810(3) 0.0593(5) Uani 1 1 d . . . . .
H5 H 0.745651 1.246806 0.853307 0.071 Uiso 1 1 calc R U . . .
C6 C 0.78840(11) 1.2490(3) 0.80919(3) 0.0517(4) Uani 1 1 d . . . . .
H6 H 0.774410 1.380845 0.804973 0.062 Uiso 1 1 calc R U . . .
C7 C 0.84771(10) 1.2265(2) 0.75661(3) 0.0425(3) Uani 1 1 d . . . . .
H7C H 0.8299(11) 1.367(2) 0.7549(3) 0.051 Uiso 1 1 d . U . . .
C8 C 0.91202(9) 1.2289(2) 0.70747(3) 0.0389(3) Uani 1 1 d . . . . .
C9 C 0.93632(10) 1.4269(2) 0.70733(3) 0.0437(3) Uani 1 1 d . . . . .
H9 H 0.932953 1.502461 0.725582 0.052 Uiso 1 1 calc R U . . .
C10 C 0.96541(11) 1.5123(2) 0.68035(3) 0.0478(4) Uani 1 1 d . . . . .
H10 H 0.980851 1.645327 0.680389 0.057 Uiso 1 1 calc R U . . .
C11 C 0.97165(11) 1.4006(2) 0.65324(3) 0.0459(4) Uani 1 1 d . . . . .
H11 H 0.991370 1.458543 0.635083 0.055 Uiso 1 1 calc R U . . .
C12 C 0.94854(10) 1.2021(2) 0.65306(3) 0.0402(3) Uani 1 1 d . . . . .
C13 C 0.91915(10) 1.1156(2) 0.68027(3) 0.0397(3) Uani 1 1 d . . . . .
H13 H 0.904281 0.982348 0.680302 0.048 Uiso 1 1 calc R U . . .
C14 C 0.95699(10) 1.0869(2) 0.62338(3) 0.0449(4) Uani 1 1 d . . . . .
O4 O 0.84657(10) 0.28633(18) 0.46575(3) 0.0712(4) Uani 1 1 d . . . . .
N2 N 0.91291(10) 0.7562(2) 0.56524(3) 0.0537(3) Uani 1 1 d . . . . .
N3 N 0.85332(9) 0.61833(19) 0.46762(3) 0.0480(3) Uani 1 1 d . . . . .
H3B H 0.847565 0.721089 0.455632 0.058 Uiso 1 1 calc R U . . .
C15 C 0.90834(13) 0.8911(3) 0.54206(3) 0.0559(4) Uani 1 1 d . . . . .
H15 H 0.918931 1.021781 0.547961 0.067 Uiso 1 1 calc R U . . .
C16 C 0.88891(12) 0.8481(2) 0.51000(3) 0.0520(4) Uani 1 1 d . . . . .
H16 H 0.886072 0.947938 0.494822 0.062 Uiso 1 1 calc R U . . .
C17 C 0.87353(10) 0.6542(2) 0.50043(3) 0.0427(3) Uani 1 1 d . . . . .
C18 C 0.87735(13) 0.5120(2) 0.52420(3) 0.0566(4) Uani 1 1 d . . . . .
H18 H 0.867064 0.380241 0.519000 0.068 Uiso 1 1 calc R U . . .
C19 C 0.89687(13) 0.5713(3) 0.55591(3) 0.0606(5) Uani 1 1 d . . . . .
H19 H 0.898878 0.475138 0.571695 0.073 Uiso 1 1 calc R U . . .
C20 C 0.84152(12) 0.4446(2) 0.45201(3) 0.0504(4) Uani 1 1 d . . . . .
C21 C 0.82238(15) 0.4618(3) 0.41616(4) 0.0682(5) Uani 1 1 d . . . . .
H21A H 0.808550 0.596290 0.410362 0.102 Uiso 0.5 1 calc R U P . .
H21B H 0.767358 0.381360 0.408276 0.102 Uiso 0.5 1 calc R U P . .
H21C H 0.879018 0.418863 0.406921 0.102 Uiso 0.5 1 calc R U P . .
H21D H 0.828067 0.334718 0.406677 0.102 Uiso 0.5 1 calc R U P . .
H21E H 0.869259 0.549649 0.408763 0.102 Uiso 0.5 1 calc R U P . .
H21F H 0.757600 0.512146 0.410118 0.102 Uiso 0.5 1 calc R U P . .
O5 O 0.84272(10) -0.04924(19) 0.42760(3) 0.0642(4) Uani 1 1 d . . . . .
H5A H 0.8980(16) -0.062(3) 0.4192(5) 0.096 Uiso 1 1 d . U . . .
H5B H 0.8461(16) 0.062(3) 0.4384(5) 0.096 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.3569(17) . ?
O1 H1A 0.93(2) . ?
O2 C14 1.2205(16) . ?
O3 C14 1.3094(18) . ?
O3 H3A 0.8200 . ?
N1 C7 1.2855(17) . ?
N1 C8 1.4248(16) . ?
C1 C6 1.4015(19) . ?
C1 C2 1.403(2) . ?
C1 C7 1.4496(18) . ?
C2 C3 1.3942(19) . ?
C3 C4 1.375(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7C 0.987(16) . ?
C8 C9 1.389(2) . ?
C8 C13 1.3931(18) . ?
C9 C10 1.379(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.382(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.388(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.3918(18) . ?
C12 C14 1.4912(18) . ?
C13 H13 0.9300 . ?
O4 C20 1.2205(18) . ?
N2 C19 1.329(2) . ?
N2 C15 1.335(2) . ?
N3 C20 1.3523(19) . ?
N3 C17 1.3949(16) . ?
N3 H3B 0.8600 . ?
C15 C16 1.3730(19) . ?
C15 H15 0.9300 . ?
C16 C17 1.3880(19) . ?
C16 H16 0.9300 . ?
C17 C18 1.388(2) . ?
C18 C19 1.387(2) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.503(2) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C21 H21D 0.9600 . ?
C21 H21E 0.9600 . ?
C21 H21F 0.9600 . ?
O5 H5A 0.88(2) . ?
O5 H5B 0.88(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1A 105.3(13) . . ?
C14 O3 H3A 109.5 . . ?
C7 N1 C8 120.07(13) . . ?
C6 C1 C2 118.85(13) . . ?
C6 C1 C7 119.03(15) . . ?
C2 C1 C7 122.06(13) . . ?
O1 C2 C3 118.81(15) . . ?
O1 C2 C1 121.57(12) . . ?
C3 C2 C1 119.62(14) . . ?
C4 C3 C2 120.15(17) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 121.09(15) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 119.27(15) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C1 121.03(17) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
N1 C7 C1 121.81(15) . . ?
N1 C7 H7C 124.2(9) . . ?
C1 C7 H7C 113.9(9) . . ?
C9 C8 C13 119.46(12) . . ?
C9 C8 N1 123.51(12) . . ?
C13 C8 N1 116.95(13) . . ?
C10 C9 C8 120.51(13) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 120.12(14) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 120.13(13) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 119.85(13) . . ?
C11 C12 C14 118.32(12) . . ?
C13 C12 C14 121.83(14) . . ?
C12 C13 C8 119.92(14) . . ?
C12 C13 H13 120.0 . . ?
C8 C13 H13 120.0 . . ?
O2 C14 O3 123.01(13) . . ?
O2 C14 C12 121.59(15) . . ?
O3 C14 C12 115.40(12) . . ?
C19 N2 C15 116.41(13) . . ?
C20 N3 C17 129.06(13) . . ?
C20 N3 H3B 115.5 . . ?
C17 N3 H3B 115.5 . . ?
N2 C15 C16 123.79(15) . . ?
N2 C15 H15 118.1 . . ?
C16 C15 H15 118.1 . . ?
C15 C16 C17 119.43(14) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C18 C17 C16 117.61(12) . . ?
C18 C17 N3 125.15(14) . . ?
C16 C17 N3 117.22(12) . . ?
C19 C18 C17 118.39(15) . . ?
C19 C18 H18 120.8 . . ?
C17 C18 H18 120.8 . . ?
N2 C19 C18 124.36(15) . . ?
N2 C19 H19 117.8 . . ?
C18 C19 H19 117.8 . . ?
O4 C20 N3 123.08(14) . . ?
O4 C20 C21 122.45(14) . . ?
N3 C20 C21 114.47(14) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C21 H21D 109.5 . . ?
H21A C21 H21D 141.1 . . ?
H21B C21 H21D 56.3 . . ?
H21C C21 H21D 56.3 . . ?
C20 C21 H21E 109.5 . . ?
H21A C21 H21E 56.3 . . ?
H21B C21 H21E 141.1 . . ?
H21C C21 H21E 56.3 . . ?
H21D C21 H21E 109.5 . . ?
C20 C21 H21F 109.5 . . ?
H21A C21 H21F 56.3 . . ?
H21B C21 H21F 56.3 . . ?
H21C C21 H21F 141.1 . . ?
H21D C21 H21F 109.5 . . ?
H21E C21 H21F 109.5 . . ?
H5A O5 H5B 107(2) . . ?

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
C6 C1 C2 O1 -179.36(12) . . . . ?
C7 C1 C2 O1 -2.1(2) . . . . ?
C6 C1 C2 C3 0.6(2) . . . . ?
C7 C1 C2 C3 177.89(13) . . . . ?
O1 C2 C3 C4 179.14(14) . . . . ?
C1 C2 C3 C4 -0.9(2) . . . . ?
C2 C3 C4 C5 0.6(2) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C4 C5 C6 C1 -0.2(2) . . . . ?
C2 C1 C6 C5 -0.1(2) . . . . ?
C7 C1 C6 C5 -177.45(13) . . . . ?
C8 N1 C7 C1 -174.52(12) . . . . ?
C6 C1 C7 N1 178.70(13) . . . . ?
C2 C1 C7 N1 1.5(2) . . . . ?
C7 N1 C8 C9 24.99(19) . . . . ?
C7 N1 C8 C13 -158.48(13) . . . . ?
C13 C8 C9 C10 1.3(2) . . . . ?
N1 C8 C9 C10 177.76(12) . . . . ?
C8 C9 C10 C11 -0.7(2) . . . . ?
C9 C10 C11 C12 0.1(2) . . . . ?
C10 C11 C12 C13 -0.1(2) . . . . ?
C10 C11 C12 C14 -179.57(13) . . . . ?
C11 C12 C13 C8 0.7(2) . . . . ?
C14 C12 C13 C8 -179.84(12) . . . . ?
C9 C8 C13 C12 -1.29(19) . . . . ?
N1 C8 C13 C12 -177.96(11) . . . . ?
C11 C12 C14 O2 4.0(2) . . . . ?
C13 C12 C14 O2 -175.47(14) . . . . ?
C11 C12 C14 O3 -175.08(13) . . . . ?
C13 C12 C14 O3 5.43(19) . . . . ?
C19 N2 C15 C16 -0.3(3) . . . . ?
N2 C15 C16 C17 -0.5(3) . . . . ?
C15 C16 C17 C18 0.9(2) . . . . ?
C15 C16 C17 N3 179.53(14) . . . . ?
C20 N3 C17 C18 -5.9(3) . . . . ?
C20 N3 C17 C16 175.58(15) . . . . ?
C16 C17 C18 C19 -0.5(2) . . . . ?
N3 C17 C18 C19 -178.99(15) . . . . ?
C15 N2 C19 C18 0.8(3) . . . . ?
C17 C18 C19 N2 -0.4(3) . . . . ?
C17 N3 C20 O4 0.8(3) . . . . ?
C17 N3 C20 C21 -178.76(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 H1A N1 0.93(2) 1.77(2) 2.6219(16) 151.1(18) . yes
O3 H3A N2 0.82 1.83 2.6476(15) 176.0 . yes
N3 H3B O5 0.86 1.95 2.8130(18) 176.3 1_565 yes
C15 H15 O2 0.93 2.47 3.1462(19) 129.3 . yes
C16 H16 O4 0.93 2.63 3.526(2) 161.2 1_565 yes
C18 H18 O4 0.93 2.31 2.8849(19) 119.4 . yes
C21 H21A O5 0.96 2.55 3.369(2) 143.8 1_565 yes
O5 H5A O2 0.88(2) 1.97(2) 2.8364(18) 165(2) 5_766 yes
O5 H5B O4 0.88(2) 1.91(2) 2.7882(17) 173(2) . yes

_refine_diff_density_max         0.160
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_shelxl_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1900763'
loop_
_audit_author_name
_audit_author_address
'Haruki Sugiyama'
;Keio University
Japan
;
_audit_update_record             
;
2019-03-04 deposited with the CCDC.	2019-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H19 N3 O4'
_chemical_formula_sum            'C21 H19 N3 O4'
_chemical_formula_weight         377.39

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   7.91100(10)
_cell_length_b                   11.6159(2)
_cell_length_c                   40.0826(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3683.33(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    28732
_cell_measurement_theta_min      3.31
_cell_measurement_theta_max      68.18

_exptl_crystal_description       chip
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             1584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.790
_shelx_estimated_absorpt_T_min   0.852
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.851
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   'Absorption was corrected by ABSCOR'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID-II IP Area Detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39460
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_theta_min         4.412
_diffrn_reflns_theta_max         68.204
_diffrn_reflns_theta_full        67.686
_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             3359
_reflns_number_gt                2382
_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       'PROCESS-AUTO (Rigaku, 1998)'
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  'SHELXL-2018/8 (Sheldrick, 2018)'
_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)+(0.0666P)²+1.2182P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3359
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1527
_refine_ls_wR_factor_gt          0.1261
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.133
_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 -0.2039(3) -0.14500(15) 0.21186(5) 0.0802(6) Uani 1 1 d . . . . .
H1B H -0.183(4) -0.099(3) 0.1916(8) 0.120 Uiso 1 1 d . U . . .
O2 O 0.1251(3) -0.07076(13) 0.06055(4) 0.0717(5) Uani 1 1 d . . . . .
O3 O 0.1173(2) 0.09074(14) 0.03162(4) 0.0648(5) Uani 1 1 d . . . . .
N1 N -0.1232(3) 0.03023(16) 0.17305(4) 0.0577(5) Uani 1 1 d . . . . .
C1 C -0.1011(3) 0.03532(19) 0.23291(5) 0.0535(5) Uani 1 1 d . . . . .
C2 C -0.1613(3) -0.0769(2) 0.23799(5) 0.0594(6) Uani 1 1 d . . . . .
C3 C -0.1777(4) -0.1187(2) 0.27016(6) 0.0727(7) Uani 1 1 d . . . . .
H3 H -0.220342 -0.192343 0.273635 0.087 Uiso 1 1 calc R U . . .
C4 C -0.1316(4) -0.0525(3) 0.29687(6) 0.0807(8) Uani 1 1 d . . . . .
H4 H -0.143357 -0.081574 0.318356 0.097 Uiso 1 1 calc R U . . .
C5 C -0.0678(4) 0.0572(2) 0.29232(6) 0.0751(8) Uani 1 1 d . . . . .
H5 H -0.034663 0.101294 0.310537 0.090 Uiso 1 1 calc R U . . .
C6 C -0.0541(3) 0.0999(2) 0.26059(5) 0.0671(7) Uani 1 1 d . . . . .
H6 H -0.012204 0.173922 0.257491 0.081 Uiso 1 1 calc R U . . .
C7 C -0.0871(3) 0.0852(2) 0.19993(5) 0.0571(6) Uani 1 1 d . . . . .
H7C H -0.049(3) 0.164(2) 0.1993(6) 0.069 Uiso 1 1 d . U . . .
C8 C -0.1114(3) 0.08962(18) 0.14216(5) 0.0526(5) Uani 1 1 d . . . . .
C9 C -0.1758(3) 0.1998(2) 0.13781(6) 0.0611(6) Uani 1 1 d . . . . .
H9 H -0.233153 0.235989 0.155137 0.073 Uiso 1 1 calc R U . . .
C10 C -0.1542(3) 0.2555(2) 0.10762(6) 0.0659(6) Uani 1 1 d . . . . .
H10 H -0.197850 0.329198 0.104698 0.079 Uiso 1 1 calc R U . . .
C11 C -0.0686(3) 0.20290(19) 0.08176(5) 0.0574(6) Uani 1 1 d . . . . .
H11 H -0.051519 0.242167 0.061822 0.069 Uiso 1 1 calc R U . . .
C12 C -0.0078(3) 0.09152(18) 0.08546(5) 0.0491(5) Uani 1 1 d . . . . .
C13 C -0.0327(3) 0.03512(18) 0.11551(5) 0.0520(5) Uani 1 1 d . . . . .
H13 H 0.004010 -0.040502 0.117880 0.062 Uiso 1 1 calc R U . . .
C14 C 0.0845(3) 0.03190(19) 0.05745(5) 0.0528(5) Uani 1 1 d . . . . .
O4 O 0.5927(3) -0.06609(16) -0.12274(4) 0.0812(6) Uani 1 1 d . . . . .
N2 N 0.2925(2) -0.03699(17) -0.00943(4) 0.0592(5) Uani 1 1 d . . . . .
H1A H 0.230958 -0.003842 0.005428 0.071 Uiso 1 1 calc R U . . .
N3 N 0.5723(2) -0.20259(15) -0.08194(4) 0.0530(5) Uani 1 1 d . . . . .
H3A H 0.601869 -0.271764 -0.076999 0.064 Uiso 1 1 calc R U . . .
C15 C 0.3361(3) 0.0195(2) -0.03685(6) 0.0603(6) Uani 1 1 d . . . . .
H15 H 0.300162 0.095218 -0.039455 0.072 Uiso 1 1 calc R U . . .
C16 C 0.4316(3) -0.02905(19) -0.06131(6) 0.0582(6) Uani 1 1 d . . . . .
H16 H 0.461657 0.013245 -0.080094 0.070 Uiso 1 1 calc R U . . .
C17 C 0.4839(3) -0.14324(18) -0.05785(5) 0.0479(5) Uani 1 1 d . . . . .
C18 C 0.4396(3) -0.20134(19) -0.02848(5) 0.0530(5) Uani 1 1 d . . . . .
H18 H 0.474575 -0.276849 -0.025047 0.064 Uiso 1 1 calc R U . . .
C19 C 0.3442(3) -0.1460(2) -0.00485(5) 0.0578(6) Uani 1 1 d . . . . .
H19 H 0.314887 -0.184559 0.014651 0.069 Uiso 1 1 calc R U . . .
C20 C 0.6188(3) -0.1632(2) -0.11323(5) 0.0584(6) Uani 1 1 d . . . . .
C21 C 0.7030(3) -0.2523(2) -0.13475(6) 0.0727(7) Uani 1 1 d . . . . .
H21A H 0.620935 -0.285874 -0.149478 0.109 Uiso 1 1 calc R U . . .
H21B H 0.750829 -0.311260 -0.120872 0.109 Uiso 1 1 calc R U . . .
H21C H 0.790863 -0.216731 -0.147645 0.109 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 C2 1.355(3) . ?
O1 H1B 0.99(3) . ?
O2 C14 1.241(3) . ?
O3 C14 1.267(2) . ?
N1 C7 1.285(3) . ?
N1 C8 1.420(3) . ?
C1 C6 1.390(3) . ?
C1 C2 1.402(3) . ?
C1 C7 1.448(3) . ?
C2 C3 1.384(3) . ?
C3 C4 1.368(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7C 0.97(3) . ?
C8 C9 1.388(3) . ?
C8 C13 1.390(3) . ?
C9 C10 1.383(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.381(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.388(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(3) . ?
C12 C14 1.508(3) . ?
C13 H13 0.9300 . ?
O4 C20 1.209(3) . ?
N2 C15 1.326(3) . ?
N2 C19 1.344(3) . ?
N2 H1A 0.8600 . ?
N3 C17 1.377(2) . ?
N3 C20 1.385(3) . ?
N3 H3A 0.8600 . ?
C15 C16 1.360(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.396(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.402(3) . ?
C18 C19 1.371(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.503(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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
C2 O1 H1B 106.1(19) . . ?
C7 N1 C8 118.3(2) . . ?
C6 C1 C2 118.5(2) . . ?
C6 C1 C7 119.5(2) . . ?
C2 C1 C7 122.1(2) . . ?
O1 C2 C3 119.4(2) . . ?
O1 C2 C1 121.0(2) . . ?
C3 C2 C1 119.6(2) . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 119.0(2) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 121.6(2) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
N1 C7 C1 123.3(2) . . ?
N1 C7 H7C 121.2(14) . . ?
C1 C7 H7C 115.4(14) . . ?
C9 C8 C13 119.20(19) . . ?
C9 C8 N1 122.22(19) . . ?
C13 C8 N1 118.58(19) . . ?
C10 C9 C8 119.8(2) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 118.99(19) . . ?
C13 C12 C14 119.94(19) . . ?
C11 C12 C14 121.07(19) . . ?
C12 C13 C8 121.1(2) . . ?
C12 C13 H13 119.4 . . ?
C8 C13 H13 119.4 . . ?
O2 C14 O3 123.1(2) . . ?
O2 C14 C12 119.48(19) . . ?
O3 C14 C12 117.4(2) . . ?
C15 N2 C19 120.04(19) . . ?
C15 N2 H1A 120.0 . . ?
C19 N2 H1A 120.0 . . ?
C17 N3 C20 127.20(19) . . ?
C17 N3 H3A 116.4 . . ?
C20 N3 H3A 116.4 . . ?
N2 C15 C16 122.5(2) . . ?
N2 C15 H15 118.8 . . ?
C16 C15 H15 118.8 . . ?
C15 C16 C17 119.2(2) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
N3 C17 C16 123.82(19) . . ?
N3 C17 C18 118.36(19) . . ?
C16 C17 C18 117.79(19) . . ?
C19 C18 C17 119.5(2) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
N2 C19 C18 121.0(2) . . ?
N2 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
O4 C20 N3 123.3(2) . . ?
O4 C20 C21 122.5(2) . . ?
N3 C20 C21 114.2(2) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
C6 C1 C2 O1 -177.9(2) . . . . ?
C7 C1 C2 O1 2.2(4) . . . . ?
C6 C1 C2 C3 2.2(4) . . . . ?
C7 C1 C2 C3 -177.7(2) . . . . ?
O1 C2 C3 C4 178.4(3) . . . . ?
C1 C2 C3 C4 -1.7(4) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C3 C4 C5 C6 1.2(5) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C2 C1 C6 C5 -1.1(4) . . . . ?
C7 C1 C6 C5 178.9(2) . . . . ?
C8 N1 C7 C1 177.4(2) . . . . ?
C6 C1 C7 N1 177.9(2) . . . . ?
C2 C1 C7 N1 -2.2(4) . . . . ?
C7 N1 C8 C9 -45.2(3) . . . . ?
C7 N1 C8 C13 134.8(2) . . . . ?
C13 C8 C9 C10 -2.8(4) . . . . ?
N1 C8 C9 C10 177.2(2) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C12 2.1(4) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C10 C11 C12 C14 179.4(2) . . . . ?
C11 C12 C13 C8 -2.4(3) . . . . ?
C14 C12 C13 C8 177.5(2) . . . . ?
C9 C8 C13 C12 4.2(3) . . . . ?
N1 C8 C13 C12 -175.8(2) . . . . ?
C13 C12 C14 O2 6.0(3) . . . . ?
C11 C12 C14 O2 -174.2(2) . . . . ?
C13 C12 C14 O3 -173.8(2) . . . . ?
C11 C12 C14 O3 6.1(3) . . . . ?
C19 N2 C15 C16 0.7(4) . . . . ?
N2 C15 C16 C17 1.0(4) . . . . ?
C20 N3 C17 C16 -2.3(3) . . . . ?
C20 N3 C17 C18 175.9(2) . . . . ?
C15 C16 C17 N3 176.1(2) . . . . ?
C15 C16 C17 C18 -2.1(3) . . . . ?
N3 C17 C18 C19 -176.7(2) . . . . ?
C16 C17 C18 C19 1.6(3) . . . . ?
C15 N2 C19 C18 -1.3(3) . . . . ?
C17 C18 C19 N2 0.1(3) . . . . ?
C17 N3 C20 O4 3.7(4) . . . . ?
C17 N3 C20 C21 -175.4(2) . . . . ?

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 H1B N1 0.99(3) 1.74(4) 2.640(3) 150(3) . yes
N2 H1A O2 0.86 2.49 3.126(2) 131.7 . yes
N2 H1A O3 0.86 1.77 2.613(2) 168.1 . yes
N3 H3A O2 0.86 1.95 2.800(2) 168.1 3_545 yes
C16 H16 O4 0.93 2.20 2.806(3) 121.9 . yes
C18 H18 O2 0.93 2.56 3.289(3) 135.0 3_545 yes

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.040

