# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_ic21150
_database_code_depnum_ccdc_archive 'CCDC 2125600'
loop_
_audit_author_name
_audit_author_address
'Su-Ying Chien'
;Instrumentation Center, National Taiwan University, Taipei
Taiwan
;
_audit_update_record             
;
2021-12-01 deposited with the CCDC.	2022-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H22 N2 O5'
_chemical_formula_weight         382.40

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/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                   5.73510(10)
_cell_length_b                   41.9722(12)
_cell_length_c                   8.3858(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.6440(10)
_cell_angle_gamma                90
_cell_volume                     1923.63(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9867
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      28.62

_exptl_crystal_description       columnar
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.461
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.093
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8936
_exptl_absorpt_correction_T_max  0.9595
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22898
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -54
_diffrn_reflns_limit_k_max       54
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.595
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4406
_reflns_number_gt                3754
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'Bruker SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0504P)²+0.8617P] 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         4406
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1250
_refine_ls_wR_factor_gt          0.1197
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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 0.4740(2) 0.63423(3) 0.02012(13) 0.0371(3) Uani 1 1 d . . . . .
O2 O 0.6914(2) 0.67799(3) 0.13605(14) 0.0365(3) Uani 1 1 d . . . . .
O3 O 0.0657(2) 0.62445(4) 0.23717(19) 0.0545(4) Uani 1 1 d . . . . .
O4 O 0.1914(2) 0.57930(3) 0.14823(16) 0.0420(3) Uani 1 1 d . . . . .
O5 O 1.1145(2) 0.65049(3) 0.73381(14) 0.0386(3) Uani 1 1 d . . . . .
H5 H 1.229075 0.646191 0.820788 0.058 Uiso 1 1 calc R U . . .
N1 N 0.5783(2) 0.64301(3) 0.29791(15) 0.0270(3) Uani 1 1 d . . . . .
N2 N 0.9291(2) 0.62734(3) 0.70987(16) 0.0312(3) Uani 1 1 d . . . . .
C1 C 0.4932(3) 0.61154(4) 0.32787(18) 0.0271(3) Uani 1 1 d . . . . .
H1 H 0.595462 0.594684 0.297565 0.033 Uiso 1 1 calc R U . . .
C2 C 0.5339(3) 0.61140(4) 0.51932(18) 0.0272(3) Uani 1 1 d . . . . .
H2 H 0.391564 0.622461 0.540397 0.033 Uiso 1 1 calc R U . . .
C3 C 0.7532(3) 0.63307(4) 0.57823(18) 0.0262(3) Uani 1 1 d . . . . .
C4 C 0.7306(3) 0.65918(4) 0.44971(17) 0.0262(3) Uani 1 1 d . . . . .
H4 H 0.894919 0.664366 0.438214 0.031 Uiso 1 1 calc R U . . .
C5 C 0.5763(3) 0.65071(4) 0.14138(18) 0.0293(3) Uani 1 1 d . . . . .
C6 C 0.7173(4) 0.68589(5) -0.0255(2) 0.0515(5) Uani 1 1 d . . . . .
H6A H 0.798403 0.668288 -0.064389 0.077 Uiso 1 1 calc R U . . .
H6B H 0.815915 0.705271 -0.015774 0.077 Uiso 1 1 calc R U . . .
H6C H 0.555247 0.689454 -0.105734 0.077 Uiso 1 1 calc R U . . .
C7 C 0.2240(3) 0.60652(4) 0.23134(19) 0.0316(4) Uani 1 1 d . . . . .
C8 C -0.0605(3) 0.57087(5) 0.0551(2) 0.0438(4) Uani 1 1 d . . . . .
H8A H -0.070963 0.565182 -0.061463 0.053 Uiso 1 1 calc R U . . .
H8B H -0.169774 0.589265 0.052033 0.053 Uiso 1 1 calc R U . . .
C9 C -0.1380(4) 0.54345(6) 0.1382(3) 0.0595(6) Uani 1 1 d . . . . .
H9A H -0.038738 0.524770 0.131716 0.089 Uiso 1 1 calc R U . . .
H9B H -0.310865 0.538783 0.082055 0.089 Uiso 1 1 calc R U . . .
H9C H -0.115516 0.548670 0.255822 0.089 Uiso 1 1 calc R U . . .
C10 C 0.5512(3) 0.57856(4) 0.59399(19) 0.0304(3) Uani 1 1 d . . . . .
C11 C 0.7224(3) 0.55665(4) 0.5744(2) 0.0369(4) Uani 1 1 d . . . . .
H11 H 0.836327 0.562845 0.518229 0.044 Uiso 1 1 calc R U . . .
C12 C 0.7289(4) 0.52606(5) 0.6354(2) 0.0457(5) Uani 1 1 d . . . . .
H12 H 0.845630 0.511265 0.619978 0.055 Uiso 1 1 calc R U . . .
C13 C 0.5663(4) 0.51688(5) 0.7188(3) 0.0516(5) Uani 1 1 d . . . . .
H13 H 0.569358 0.495724 0.759671 0.062 Uiso 1 1 calc R U . . .
C14 C 0.4002(4) 0.53843(5) 0.7424(3) 0.0544(5) Uani 1 1 d . . . . .
H14 H 0.290212 0.532255 0.801659 0.065 Uiso 1 1 calc R U . . .
C15 C 0.3915(3) 0.56920(5) 0.6802(2) 0.0426(4) Uani 1 1 d . . . . .
H15 H 0.275342 0.583924 0.696955 0.051 Uiso 1 1 calc R U . . .
C16 C 0.6095(3) 0.68921(4) 0.48950(18) 0.0283(3) Uani 1 1 d . . . . .
C17 C 0.7454(4) 0.71105(4) 0.6046(2) 0.0387(4) Uani 1 1 d . . . . .
H17 H 0.914783 0.707463 0.657779 0.046 Uiso 1 1 calc R U . . .
C18 C 0.6333(4) 0.73824(5) 0.6422(3) 0.0509(5) Uani 1 1 d . . . . .
H18 H 0.726969 0.753007 0.722032 0.061 Uiso 1 1 calc R U . . .
C19 C 0.3909(4) 0.74397(5) 0.5661(3) 0.0513(5) Uani 1 1 d . . . . .
H19 H 0.316682 0.762744 0.591636 0.062 Uiso 1 1 calc R U . . .
C20 C 0.2553(4) 0.72250(5) 0.4529(3) 0.0491(5) Uani 1 1 d . . . . .
H20 H 0.086190 0.726362 0.400088 0.059 Uiso 1 1 calc R U . . .
C21 C 0.3628(3) 0.69519(4) 0.4146(2) 0.0380(4) Uani 1 1 d . . . . .
H21 H 0.266478 0.680398 0.336154 0.046 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 C5 1.2227(19) . ?
O2 C5 1.329(2) . ?
O2 C6 1.445(2) . ?
O3 C7 1.192(2) . ?
O4 C7 1.322(2) . ?
O4 C8 1.462(2) . ?
O5 N2 1.4092(18) . ?
N1 C5 1.3485(19) . ?
N1 C1 1.456(2) . ?
N1 C4 1.4731(18) . ?
N2 C3 1.2726(19) . ?
C1 C7 1.525(2) . ?
C1 C2 1.551(2) . ?
C2 C10 1.505(2) . ?
C2 C3 1.509(2) . ?
C3 C4 1.515(2) . ?
C4 C16 1.524(2) . ?
C8 C9 1.482(3) . ?
C10 C15 1.385(3) . ?
C10 C11 1.391(2) . ?
C11 C12 1.379(3) . ?
C12 C13 1.380(3) . ?
C13 C14 1.371(3) . ?
C14 C15 1.388(3) . ?
C16 C21 1.386(2) . ?
C16 C17 1.387(2) . ?
C17 C18 1.392(3) . ?
C18 C19 1.364(3) . ?
C19 C20 1.368(3) . ?
C20 C21 1.385(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O2 C6 114.98(14) . . ?
C7 O4 C8 116.74(14) . . ?
C5 N1 C1 118.75(13) . . ?
C5 N1 C4 123.96(13) . . ?
C1 N1 C4 114.26(12) . . ?
C3 N2 O5 111.03(13) . . ?
N1 C1 C7 111.86(12) . . ?
N1 C1 C2 103.24(12) . . ?
C7 C1 C2 111.08(12) . . ?
C10 C2 C3 118.19(13) . . ?
C10 C2 C1 113.86(13) . . ?
C3 C2 C1 100.69(12) . . ?
N2 C3 C2 122.22(14) . . ?
N2 C3 C4 128.93(14) . . ?
C2 C3 C4 108.66(12) . . ?
N1 C4 C3 100.49(12) . . ?
N1 C4 C16 112.34(12) . . ?
C3 C4 C16 112.89(12) . . ?
O1 C5 O2 125.27(15) . . ?
O1 C5 N1 122.30(16) . . ?
O2 C5 N1 112.42(13) . . ?
O3 C7 O4 125.42(15) . . ?
O3 C7 C1 123.52(15) . . ?
O4 C7 C1 111.00(14) . . ?
O4 C8 C9 108.98(16) . . ?
C15 C10 C11 118.45(16) . . ?
C15 C10 C2 120.42(15) . . ?
C11 C10 C2 121.11(15) . . ?
C12 C11 C10 120.84(18) . . ?
C11 C12 C13 120.12(19) . . ?
C14 C13 C12 119.67(19) . . ?
C13 C14 C15 120.5(2) . . ?
C10 C15 C14 120.39(19) . . ?
C21 C16 C17 118.49(16) . . ?
C21 C16 C4 121.37(14) . . ?
C17 C16 C4 120.13(15) . . ?
C16 C17 C18 119.92(18) . . ?
C19 C18 C17 120.93(19) . . ?
C18 C19 C20 119.53(19) . . ?
C19 C20 C21 120.5(2) . . ?
C20 C21 C16 120.64(18) . . ?

_refine_diff_density_max         0.313
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.038

