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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_D43XB112_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2047315'
loop_
_audit_author_name
_audit_author_address
'Merce Font Bardia'
;University of Barcelona
Spain
;
_audit_update_record             
;
2020-11-30 deposited with the CCDC.	2021-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        c-18b
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H27 N O5'
_chemical_formula_sum            'C21 H27 N O5'
_chemical_formula_weight         373.43

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

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

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

_cell_length_a                   9.6698(8)
_cell_length_b                   13.6733(12)
_cell_length_c                   15.2154(12)
_cell_angle_alpha                107.614(4)
_cell_angle_beta                 91.299(4)
_cell_angle_gamma                93.979(4)
_cell_volume                     1910.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9825
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      31.04

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.680
_exptl_crystal_size_mid          0.365
_exptl_crystal_size_min          0.257
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6572
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            77889
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.404
_diffrn_reflns_theta_max         31.071
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             12102
_reflns_number_gt                10099
_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'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0533P)²+0.7740P] 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         12102
_refine_ls_number_parameters     491
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1196
_refine_ls_wR_factor_gt          0.1124
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
O1A O 1.01338(8) 0.34578(6) 0.13373(6) 0.01900(16) Uani 1 1 d . . . . .
O2A O 0.88404(10) -0.08503(6) 0.19561(6) 0.02560(19) Uani 1 1 d . . . . .
O3A O 0.98297(10) -0.11217(6) 0.05533(6) 0.02393(18) Uani 1 1 d . . . . .
O4A O 0.92143(9) 0.36929(7) 0.36413(6) 0.02571(19) Uani 1 1 d . . . . .
O5A O 1.15356(8) 0.36479(6) 0.37452(5) 0.01763(15) Uani 1 1 d . . . . .
N1A N 0.83844(9) 0.22793(7) 0.14556(6) 0.01335(16) Uani 1 1 d . . . . .
C1A C 0.96403(10) 0.28120(8) 0.16740(7) 0.01359(18) Uani 1 1 d . . . . .
C2A C 1.03477(10) 0.24750(8) 0.24341(7) 0.01475(18) Uani 1 1 d . . . . .
H2A H 1.133393 0.233983 0.229200 0.018 Uiso 1 1 calc R U . . .
C3A C 0.94815(11) 0.14624(8) 0.23994(7) 0.01461(18) Uani 1 1 d . . . . .
C4A C 1.01226(11) 0.05852(8) 0.16608(7) 0.01566(19) Uani 1 1 d . . . . .
H4AA H 1.042624 0.084845 0.115175 0.019 Uiso 1 1 calc R U . . .
H4AB H 1.095826 0.039777 0.194130 0.019 Uiso 1 1 calc R U . . .
C5A C 0.91543(12) -0.03804(8) 0.12575(7) 0.0184(2) Uani 1 1 d . . . . .
C6A C 0.88182(13) -0.19403(9) 0.15297(9) 0.0233(2) Uani 1 1 d . . . . .
H6AA H 0.790221 -0.222847 0.122207 0.028 Uiso 1 1 calc R U . . .
H6AB H 0.904791 -0.229748 0.198476 0.028 Uiso 1 1 calc R U . . .
C7A C 0.99316(12) -0.20212(9) 0.08355(8) 0.0207(2) Uani 1 1 d . . . . .
H7AA H 1.086022 -0.202263 0.112262 0.025 Uiso 1 1 calc R U . . .
H7AB H 0.975331 -0.265426 0.030533 0.025 Uiso 1 1 calc R U . . .
C8A C 0.78393(12) -0.01188(9) 0.08360(8) 0.0209(2) Uani 1 1 d . . . . .
H8AA H 0.721093 -0.075033 0.057816 0.025 Uiso 1 1 calc R U . . .
H8AB H 0.807876 0.016443 0.032718 0.025 Uiso 1 1 calc R U . . .
C9A C 0.71091(11) 0.06714(9) 0.15747(8) 0.0193(2) Uani 1 1 d . . . . .
H9AA H 0.628391 0.086080 0.128488 0.023 Uiso 1 1 calc R U . . .
H9AB H 0.678162 0.035119 0.204325 0.023 Uiso 1 1 calc R U . . .
C10A C 0.80309(10) 0.16467(8) 0.20556(7) 0.01421(18) Uani 1 1 d . . . . .
H10A H 0.754030 0.206857 0.259474 0.017 Uiso 1 1 calc R U . . .
C11A C 0.73865(11) 0.24674(9) 0.08095(7) 0.01649(19) Uani 1 1 d . . . . .
H11A H 0.711585 0.181086 0.032205 0.020 Uiso 1 1 calc R U . . .
H11B H 0.783713 0.294759 0.050950 0.020 Uiso 1 1 calc R U . . .
C12A C 0.60877(10) 0.29146(8) 0.12535(7) 0.01547(19) Uani 1 1 d . . . . .
C13A C 0.47976(11) 0.25805(10) 0.07986(8) 0.0219(2) Uani 1 1 d . . . . .
H13A H 0.472779 0.203957 0.023038 0.026 Uiso 1 1 calc R U . . .
C14A C 0.36046(12) 0.30325(11) 0.11691(9) 0.0257(2) Uani 1 1 d . . . . .
H14A H 0.272879 0.280095 0.085158 0.031 Uiso 1 1 calc R U . . .
C15A C 0.36961(12) 0.38158(10) 0.19965(9) 0.0236(2) Uani 1 1 d . . . . .
H15A H 0.288614 0.413014 0.224440 0.028 Uiso 1 1 calc R U . . .
C16A C 0.49780(12) 0.41442(9) 0.24670(9) 0.0227(2) Uani 1 1 d . . . . .
H16A H 0.504070 0.467711 0.304040 0.027 Uiso 1 1 calc R U . . .
C17A C 0.61719(11) 0.36911(8) 0.20971(8) 0.0190(2) Uani 1 1 d . . . . .
H17A H 0.704408 0.391332 0.242185 0.023 Uiso 1 1 calc R U . . .
C18A C 1.02762(11) 0.33355(8) 0.33353(7) 0.01619(19) Uani 1 1 d . . . . .
C19A C 1.15920(11) 0.45006(8) 0.46057(7) 0.0179(2) Uani 1 1 d . . . . .
H19A H 1.106931 0.429178 0.508045 0.021 Uiso 1 1 calc R U . . .
H19B H 1.117402 0.509961 0.450214 0.021 Uiso 1 1 calc R U . . .
C20A C 1.30940(12) 0.47790(10) 0.49212(8) 0.0232(2) Uani 1 1 d . . . . .
H20A H 1.349848 0.417973 0.501744 0.035 Uiso 1 1 calc R U . . .
H20B H 1.316307 0.534566 0.550142 0.035 Uiso 1 1 calc R U . . .
H20C H 1.359847 0.499292 0.444996 0.035 Uiso 1 1 calc R U . . .
C21A C 0.94373(13) 0.12594(9) 0.33326(7) 0.0212(2) Uani 1 1 d . . . . .
H21A H 0.886493 0.061917 0.326792 0.032 Uiso 1 1 calc R U . . .
H21B H 0.903752 0.183215 0.378210 0.032 Uiso 1 1 calc R U . . .
H21C H 1.038111 0.119656 0.354637 0.032 Uiso 1 1 calc R U . . .
O1B O 0.46204(8) 0.65255(6) 0.37096(5) 0.01786(15) Uani 1 1 d . . . . .
O2B O 0.38484(11) 1.07750(7) 0.30185(6) 0.0278(2) Uani 1 1 d . . . . .
O3B O 0.49822(10) 1.11196(6) 0.44328(6) 0.02606(19) Uani 1 1 d . . . . .
O4B O 0.57834(9) 0.64378(7) 0.12069(6) 0.02592(19) Uani 1 1 d . . . . .
O5B O 0.35095(8) 0.62410(6) 0.14503(5) 0.01736(15) Uani 1 1 d . . . . .
N1B N 0.30205(9) 0.76433(7) 0.35643(6) 0.01330(16) Uani 1 1 d . . . . .
C1B C 0.41900(10) 0.71485(8) 0.33584(7) 0.01338(18) Uani 1 1 d . . . . .
C2B C 0.49038(10) 0.75096(8) 0.26109(7) 0.01442(18) Uani 1 1 d . . . . .
H2B H 0.590415 0.771421 0.280389 0.017 Uiso 1 1 calc R U . . .
C3B C 0.41630(11) 0.84870(8) 0.26210(7) 0.01466(18) Uani 1 1 d . . . . .
C4B C 0.49706(11) 0.93988(8) 0.33556(7) 0.01674(19) Uani 1 1 d . . . . .
H4BA H 0.527465 0.915841 0.387538 0.020 Uiso 1 1 calc R U . . .
H4BB H 0.581457 0.960837 0.307986 0.020 Uiso 1 1 calc R U . . .
C5B C 0.41568(13) 1.03381(8) 0.37361(8) 0.0202(2) Uani 1 1 d . . . . .
C6B C 0.40584(13) 1.18636(9) 0.34042(9) 0.0233(2) Uani 1 1 d . . . . .
H6BA H 0.321749 1.215829 0.370161 0.028 Uiso 1 1 calc R U . . .
H6BB H 0.432018 1.219364 0.292916 0.028 Uiso 1 1 calc R U . . .
C7B C 0.52389(12) 1.19871(9) 0.41077(8) 0.0208(2) Uani 1 1 d . . . . .
H7BA H 0.614741 1.197336 0.381882 0.025 Uiso 1 1 calc R U . . .
H7BB H 0.521964 1.263961 0.461618 0.025 Uiso 1 1 calc R U . . .
C8B C 0.28422(12) 1.00410(9) 0.41535(8) 0.0216(2) Uani 1 1 d . . . . .
H8BA H 0.231439 1.065367 0.439832 0.026 Uiso 1 1 calc R U . . .
H8BB H 0.308572 0.977830 0.467146 0.026 Uiso 1 1 calc R U . . .
C9B C 0.19500(12) 0.92118(9) 0.34182(8) 0.0193(2) Uani 1 1 d . . . . .
H9BA H 0.112014 0.900117 0.370679 0.023 Uiso 1 1 calc R U . . .
H9BB H 0.162726 0.950929 0.293943 0.023 Uiso 1 1 calc R U . . .
C10B C 0.27072(10) 0.82591(8) 0.29555(7) 0.01415(18) Uani 1 1 d . . . . .
H10B H 0.211965 0.781466 0.241336 0.017 Uiso 1 1 calc R U . . .
C11B C 0.20461(10) 0.74369(9) 0.42145(7) 0.01633(19) Uani 1 1 d . . . . .
H11C H 0.194990 0.808386 0.471638 0.020 Uiso 1 1 calc R U . . .
H11D H 0.242759 0.694076 0.449441 0.020 Uiso 1 1 calc R U . . .
C12B C 0.06270(10) 0.70073(8) 0.37734(7) 0.01562(19) Uani 1 1 d . . . . .
C13B C 0.04798(11) 0.61622(9) 0.29799(8) 0.0197(2) Uani 1 1 d . . . . .
H13B H 0.128022 0.585882 0.270267 0.024 Uiso 1 1 calc R U . . .
C14B C -0.08331(12) 0.57589(9) 0.25901(9) 0.0228(2) Uani 1 1 d . . . . .
H14B H -0.092654 0.518619 0.204527 0.027 Uiso 1 1 calc R U . . .
C15B C -0.20096(12) 0.61957(9) 0.29996(9) 0.0225(2) Uani 1 1 d . . . . .
H15B H -0.290572 0.591566 0.273744 0.027 Uiso 1 1 calc R U . . .
C16B C -0.18752(11) 0.70378(10) 0.37884(8) 0.0216(2) Uani 1 1 d . . . . .
H16B H -0.267799 0.733444 0.406825 0.026 Uiso 1 1 calc R U . . .
C17B C -0.05588(11) 0.74489(9) 0.41706(8) 0.0193(2) Uani 1 1 d . . . . .
H17B H -0.046756 0.803395 0.470520 0.023 Uiso 1 1 calc R U . . .
C18B C 0.48061(11) 0.66689(8) 0.16862(7) 0.01607(19) Uani 1 1 d . . . . .
C19B C 0.33394(12) 0.54709(9) 0.05370(7) 0.0182(2) Uani 1 1 d . . . . .
H19C H 0.386281 0.487005 0.052457 0.022 Uiso 1 1 calc R U . . .
H19D H 0.369553 0.576857 0.006062 0.022 Uiso 1 1 calc R U . . .
C20B C 0.18148(12) 0.51447(10) 0.03488(9) 0.0238(2) Uani 1 1 d . . . . .
H20D H 0.130441 0.574782 0.037873 0.036 Uiso 1 1 calc R U . . .
H20E H 0.148025 0.483092 0.081233 0.036 Uiso 1 1 calc R U . . .
H20F H 0.166720 0.464317 -0.026716 0.036 Uiso 1 1 calc R U . . .
C21B C 0.40808(13) 0.86675(9) 0.16768(7) 0.0204(2) Uani 1 1 d . . . . .
H21D H 0.502068 0.878032 0.147989 0.031 Uiso 1 1 calc R U . . .
H21E H 0.357078 0.927420 0.172099 0.031 Uiso 1 1 calc R U . . .
H21F H 0.359836 0.806363 0.122508 0.031 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
O1A C1A 1.2233(13) . ?
O2A C5A 1.4268(13) . ?
O2A C6A 1.4326(14) . ?
O3A C7A 1.4288(14) . ?
O3A C5A 1.4382(13) . ?
O4A C18A 1.2098(13) . ?
O5A C18A 1.3367(12) . ?
O5A C19A 1.4631(13) . ?
N1A C1A 1.3521(13) . ?
N1A C11A 1.4520(13) . ?
N1A C10A 1.4661(13) . ?
C1A C2A 1.5324(14) . ?
C2A C18A 1.5194(14) . ?
C2A C3A 1.5538(15) . ?
C2A H2A 1.0000 . ?
C3A C21A 1.5280(14) . ?
C3A C10A 1.5493(14) . ?
C3A C4A 1.5507(14) . ?
C4A C5A 1.5194(16) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C5A C8A 1.5236(17) . ?
C6A C7A 1.5113(16) . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C8A C9A 1.5284(16) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C9A C10A 1.5242(15) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C10A H10A 1.0000 . ?
C11A C12A 1.5175(14) . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C12A C13A 1.3909(15) . ?
C12A C17A 1.3927(15) . ?
C13A C14A 1.3958(16) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.3804(19) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.3923(17) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.3969(15) . ?
C16A H16A 0.9500 . ?
C17A H17A 0.9500 . ?
C19A C20A 1.5053(15) . ?
C19A H19A 0.9900 . ?
C19A H19B 0.9900 . ?
C20A H20A 0.9800 . ?
C20A H20B 0.9800 . ?
C20A H20C 0.9800 . ?
C21A H21A 0.9800 . ?
C21A H21B 0.9800 . ?
C21A H21C 0.9800 . ?
O1B C1B 1.2243(12) . ?
O2B C6B 1.4231(14) . ?
O2B C5B 1.4291(13) . ?
O3B C7B 1.4259(14) . ?
O3B C5B 1.4353(13) . ?
O4B C18B 1.2075(13) . ?
O5B C18B 1.3393(13) . ?
O5B C19B 1.4653(13) . ?
N1B C1B 1.3523(12) . ?
N1B C11B 1.4562(13) . ?
N1B C10B 1.4675(13) . ?
C1B C2B 1.5305(14) . ?
C2B C18B 1.5199(14) . ?
C2B C3B 1.5557(15) . ?
C2B H2B 1.0000 . ?
C3B C21B 1.5308(14) . ?
C3B C4B 1.5477(14) . ?
C3B C10B 1.5509(14) . ?
C4B C5B 1.5215(16) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C5B C8B 1.5184(18) . ?
C6B C7B 1.5119(16) . ?
C6B H6BA 0.9900 . ?
C6B H6BB 0.9900 . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C8B C9B 1.5279(16) . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C9B C10B 1.5262(15) . ?
C9B H9BA 0.9900 . ?
C9B H9BB 0.9900 . ?
C10B H10B 1.0000 . ?
C11B C12B 1.5121(14) . ?
C11B H11C 0.9900 . ?
C11B H11D 0.9900 . ?
C12B C13B 1.3922(16) . ?
C12B C17B 1.3969(15) . ?
C13B C14B 1.3923(16) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.3930(17) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.3853(18) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.3942(16) . ?
C16B H16B 0.9500 . ?
C17B H17B 0.9500 . ?
C19B C20B 1.5056(16) . ?
C19B H19C 0.9900 . ?
C19B H19D 0.9900 . ?
C20B H20D 0.9800 . ?
C20B H20E 0.9800 . ?
C20B H20F 0.9800 . ?
C21B H21D 0.9800 . ?
C21B H21E 0.9800 . ?
C21B H21F 0.9800 . ?

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
C5A O2A C6A 106.81(8) . . ?
C7A O3A C5A 108.22(8) . . ?
C18A O5A C19A 115.91(8) . . ?
C1A N1A C11A 122.64(9) . . ?
C1A N1A C10A 113.44(8) . . ?
C11A N1A C10A 122.95(8) . . ?
O1A C1A N1A 126.71(10) . . ?
O1A C1A C2A 125.35(9) . . ?
N1A C1A C2A 107.94(9) . . ?
C18A C2A C1A 107.45(8) . . ?
C18A C2A C3A 114.06(9) . . ?
C1A C2A C3A 103.18(8) . . ?
C18A C2A H2A 110.6 . . ?
C1A C2A H2A 110.6 . . ?
C3A C2A H2A 110.6 . . ?
C21A C3A C10A 112.00(9) . . ?
C21A C3A C4A 111.83(8) . . ?
C10A C3A C4A 110.57(8) . . ?
C21A C3A C2A 113.38(9) . . ?
C10A C3A C2A 102.15(8) . . ?
C4A C3A C2A 106.39(8) . . ?
C5A C4A C3A 114.70(9) . . ?
C5A C4A H4AA 108.6 . . ?
C3A C4A H4AA 108.6 . . ?
C5A C4A H4AB 108.6 . . ?
C3A C4A H4AB 108.6 . . ?
H4AA C4A H4AB 107.6 . . ?
O2A C5A O3A 106.52(8) . . ?
O2A C5A C4A 109.80(9) . . ?
O3A C5A C4A 110.03(9) . . ?
O2A C5A C8A 111.26(9) . . ?
O3A C5A C8A 109.01(9) . . ?
C4A C5A C8A 110.15(9) . . ?
O2A C6A C7A 102.15(9) . . ?
O2A C6A H6AA 111.3 . . ?
C7A C6A H6AA 111.3 . . ?
O2A C6A H6AB 111.3 . . ?
C7A C6A H6AB 111.3 . . ?
H6AA C6A H6AB 109.2 . . ?
O3A C7A C6A 103.54(9) . . ?
O3A C7A H7AA 111.1 . . ?
C6A C7A H7AA 111.1 . . ?
O3A C7A H7AB 111.1 . . ?
C6A C7A H7AB 111.1 . . ?
H7AA C7A H7AB 109.0 . . ?
C5A C8A C9A 109.74(9) . . ?
C5A C8A H8AA 109.7 . . ?
C9A C8A H8AA 109.7 . . ?
C5A C8A H8AB 109.7 . . ?
C9A C8A H8AB 109.7 . . ?
H8AA C8A H8AB 108.2 . . ?
C10A C9A C8A 113.49(9) . . ?
C10A C9A H9AA 108.9 . . ?
C8A C9A H9AA 108.9 . . ?
C10A C9A H9AB 108.9 . . ?
C8A C9A H9AB 108.9 . . ?
H9AA C9A H9AB 107.7 . . ?
N1A C10A C9A 113.60(9) . . ?
N1A C10A C3A 102.09(8) . . ?
C9A C10A C3A 114.88(9) . . ?
N1A C10A H10A 108.6 . . ?
C9A C10A H10A 108.6 . . ?
C3A C10A H10A 108.6 . . ?
N1A C11A C12A 113.67(8) . . ?
N1A C11A H11A 108.8 . . ?
C12A C11A H11A 108.8 . . ?
N1A C11A H11B 108.8 . . ?
C12A C11A H11B 108.8 . . ?
H11A C11A H11B 107.7 . . ?
C13A C12A C17A 119.14(10) . . ?
C13A C12A C11A 119.95(10) . . ?
C17A C12A C11A 120.86(9) . . ?
C12A C13A C14A 120.62(11) . . ?
C12A C13A H13A 119.7 . . ?
C14A C13A H13A 119.7 . . ?
C15A C14A C13A 120.06(11) . . ?
C15A C14A H14A 120.0 . . ?
C13A C14A H14A 120.0 . . ?
C14A C15A C16A 119.87(10) . . ?
C14A C15A H15A 120.1 . . ?
C16A C15A H15A 120.1 . . ?
C15A C16A C17A 120.09(11) . . ?
C15A C16A H16A 120.0 . . ?
C17A C16A H16A 120.0 . . ?
C12A C17A C16A 120.21(10) . . ?
C12A C17A H17A 119.9 . . ?
C16A C17A H17A 119.9 . . ?
O4A C18A O5A 124.37(10) . . ?
O4A C18A C2A 124.26(9) . . ?
O5A C18A C2A 111.37(8) . . ?
O5A C19A C20A 107.67(9) . . ?
O5A C19A H19A 110.2 . . ?
C20A C19A H19A 110.2 . . ?
O5A C19A H19B 110.2 . . ?
C20A C19A H19B 110.2 . . ?
H19A C19A H19B 108.5 . . ?
C19A C20A H20A 109.5 . . ?
C19A C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
C19A C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C3A C21A H21A 109.5 . . ?
C3A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
C3A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C6B O2B C5B 107.30(9) . . ?
C7B O3B C5B 108.21(8) . . ?
C18B O5B C19B 114.74(8) . . ?
C1B N1B C11B 122.67(9) . . ?
C1B N1B C10B 113.48(8) . . ?
C11B N1B C10B 122.99(8) . . ?
O1B C1B N1B 126.46(10) . . ?
O1B C1B C2B 125.39(9) . . ?
N1B C1B C2B 108.14(8) . . ?
C18B C2B C1B 111.70(8) . . ?
C18B C2B C3B 114.68(8) . . ?
C1B C2B C3B 103.29(8) . . ?
C18B C2B H2B 109.0 . . ?
C1B C2B H2B 109.0 . . ?
C3B C2B H2B 109.0 . . ?
C21B C3B C4B 111.82(9) . . ?
C21B C3B C10B 112.08(8) . . ?
C4B C3B C10B 110.49(8) . . ?
C21B C3B C2B 113.27(9) . . ?
C4B C3B C2B 106.24(8) . . ?
C10B C3B C2B 102.43(8) . . ?
C5B C4B C3B 114.84(9) . . ?
C5B C4B H4BA 108.6 . . ?
C3B C4B H4BA 108.6 . . ?
C5B C4B H4BB 108.6 . . ?
C3B C4B H4BB 108.6 . . ?
H4BA C4B H4BB 107.5 . . ?
O2B C5B O3B 106.42(9) . . ?
O2B C5B C8B 111.32(10) . . ?
O3B C5B C8B 109.14(9) . . ?
O2B C5B C4B 109.71(9) . . ?
O3B C5B C4B 110.21(9) . . ?
C8B C5B C4B 109.98(9) . . ?
O2B C6B C7B 102.32(9) . . ?
O2B C6B H6BA 111.3 . . ?
C7B C6B H6BA 111.3 . . ?
O2B C6B H6BB 111.3 . . ?
C7B C6B H6BB 111.3 . . ?
H6BA C6B H6BB 109.2 . . ?
O3B C7B C6B 103.26(9) . . ?
O3B C7B H7BA 111.1 . . ?
C6B C7B H7BA 111.1 . . ?
O3B C7B H7BB 111.1 . . ?
C6B C7B H7BB 111.1 . . ?
H7BA C7B H7BB 109.1 . . ?
C5B C8B C9B 109.72(9) . . ?
C5B C8B H8BA 109.7 . . ?
C9B C8B H8BA 109.7 . . ?
C5B C8B H8BB 109.7 . . ?
C9B C8B H8BB 109.7 . . ?
H8BA C8B H8BB 108.2 . . ?
C10B C9B C8B 113.63(9) . . ?
C10B C9B H9BA 108.8 . . ?
C8B C9B H9BA 108.8 . . ?
C10B C9B H9BB 108.8 . . ?
C8B C9B H9BB 108.8 . . ?
H9BA C9B H9BB 107.7 . . ?
N1B C10B C9B 114.03(9) . . ?
N1B C10B C3B 102.04(8) . . ?
C9B C10B C3B 114.76(9) . . ?
N1B C10B H10B 108.6 . . ?
C9B C10B H10B 108.6 . . ?
C3B C10B H10B 108.6 . . ?
N1B C11B C12B 113.11(8) . . ?
N1B C11B H11C 109.0 . . ?
C12B C11B H11C 109.0 . . ?
N1B C11B H11D 109.0 . . ?
C12B C11B H11D 109.0 . . ?
H11C C11B H11D 107.8 . . ?
C13B C12B C17B 119.16(10) . . ?
C13B C12B C11B 120.85(9) . . ?
C17B C12B C11B 119.98(10) . . ?
C12B C13B C14B 120.41(10) . . ?
C12B C13B H13B 119.8 . . ?
C14B C13B H13B 119.8 . . ?
C13B C14B C15B 119.95(11) . . ?
C13B C14B H14B 120.0 . . ?
C15B C14B H14B 120.0 . . ?
C16B C15B C14B 120.12(10) . . ?
C16B C15B H15B 119.9 . . ?
C14B C15B H15B 119.9 . . ?
C15B C16B C17B 119.83(10) . . ?
C15B C16B H16B 120.1 . . ?
C17B C16B H16B 120.1 . . ?
C16B C17B C12B 120.51(11) . . ?
C16B C17B H17B 119.7 . . ?
C12B C17B H17B 119.7 . . ?
O4B C18B O5B 123.99(10) . . ?
O4B C18B C2B 123.53(10) . . ?
O5B C18B C2B 112.45(9) . . ?
O5B C19B C20B 107.70(9) . . ?
O5B C19B H19C 110.2 . . ?
C20B C19B H19C 110.2 . . ?
O5B C19B H19D 110.2 . . ?
C20B C19B H19D 110.2 . . ?
H19C C19B H19D 108.5 . . ?
C19B C20B H20D 109.5 . . ?
C19B C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C19B C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
C3B C21B H21D 109.5 . . ?
C3B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
C3B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?

_refine_diff_density_max         0.482
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_D43XB86_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2047318'
loop_
_audit_author_name
_audit_author_address
'Merce Font Bardia'
;University of Barcelona
Spain
;
_audit_update_record             
;
2020-11-30 deposited with the CCDC.	2021-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        7a*
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H25 N O5'
_chemical_formula_sum            'C21 H25 N O5'
_chemical_formula_weight         371.42

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                   8.443(3)
_cell_length_b                   7.818(3)
_cell_length_c                   29.113(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.255(12)
_cell_angle_gamma                90
_cell_volume                     1910.3(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9960
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      36.96

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.608
_exptl_crystal_size_mid          0.314
_exptl_crystal_size_min          0.264
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6610
_exptl_absorpt_correction_T_max  0.7473
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35945
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         2.427
_diffrn_reflns_theta_max         35.572
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             8666
_reflns_number_gt                6865
_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'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0563P)²+0.6592P] 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         8666
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1356
_refine_ls_wR_factor_gt          0.1164
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.78317(9) -0.00799(9) 0.46329(3) 0.02471(14) Uani 1 1 d . . . . .
O2 O 0.58632(9) 0.18395(9) 0.46875(3) 0.02340(14) Uani 1 1 d . . . . .
O3 O 1.18471(10) 0.50621(12) 0.43918(3) 0.03112(17) Uani 1 1 d . . . . .
O4 O 1.07551(8) 0.40195(9) 0.37084(2) 0.02050(13) Uani 1 1 d . . . . .
O5 O 0.89524(9) 0.78784(9) 0.34678(3) 0.02530(15) Uani 1 1 d . . . . .
N1 N 0.73706(9) 0.54662(10) 0.34416(3) 0.01931(14) Uani 1 1 d . . . . .
C1 C 0.71509(11) 0.14609(11) 0.44289(3) 0.01939(15) Uani 1 1 d . . . . .
C2 C 0.84144(10) 0.28848(11) 0.44690(3) 0.01860(15) Uani 1 1 d . . . . .
H2A H 0.871004 0.315559 0.479941 0.022 Uiso 1 1 calc R U . . .
H2AB H 0.938207 0.246932 0.434029 0.022 Uiso 1 1 calc R U . . .
C3 C 0.78222(10) 0.45184(11) 0.42131(3) 0.01688(14) Uani 1 1 d . . . . .
C4 C 0.71278(10) 0.40528(11) 0.37277(3) 0.01729(14) Uani 1 1 d . . . . .
C5 C 0.64725(11) 0.25536(12) 0.36002(3) 0.02058(16) Uani 1 1 d . . . . .
H5 H 0.597438 0.242006 0.329365 0.025 Uiso 1 1 calc R U . . .
C6 C 0.64999(12) 0.10628(12) 0.39292(3) 0.02336(17) Uani 1 1 d . . . . .
H6A H 0.715415 0.014039 0.381310 0.028 Uiso 1 1 calc R U . . .
H6AB H 0.540058 0.061994 0.392698 0.028 Uiso 1 1 calc R U . . .
C7 C 0.76531(14) 0.00075(15) 0.51179(4) 0.0291(2) Uani 1 1 d . . . . .
H7A H 0.868004 0.029170 0.529923 0.035 Uiso 1 1 calc R U . . .
H7AB H 0.726408 -0.109541 0.522946 0.035 Uiso 1 1 calc R U . . .
C8 C 0.64234(14) 0.14340(14) 0.51597(4) 0.0279(2) Uani 1 1 d . . . . .
H8A H 0.553952 0.102714 0.532873 0.033 Uiso 1 1 calc R U . . .
H8AB H 0.692452 0.244293 0.532172 0.033 Uiso 1 1 calc R U . . .
C9 C 0.91442(11) 0.58291(11) 0.41141(3) 0.01862(15) Uani 1 1 d . . . . .
H9 H 0.923735 0.675309 0.435303 0.022 Uiso 1 1 calc R U . . .
C10 C 0.85066(11) 0.65612(12) 0.36409(3) 0.01956(15) Uani 1 1 d . . . . .
C11 C 1.21996(12) 0.30239(14) 0.36721(4) 0.02525(18) Uani 1 1 d . . . . .
H11A H 1.249133 0.236872 0.395990 0.030 Uiso 1 1 calc R U . . .
H11B H 1.309654 0.379010 0.362017 0.030 Uiso 1 1 calc R U . . .
C12 C 1.07453(11) 0.49701(12) 0.40902(3) 0.01970(15) Uani 1 1 d . . . . .
C13 C 1.18473(16) 0.18289(17) 0.32703(5) 0.0372(3) Uani 1 1 d . . . . .
H13A H 1.151311 0.249101 0.299060 0.056 Uiso 1 1 calc R U . . .
H13B H 1.099174 0.104330 0.333251 0.056 Uiso 1 1 calc R U . . .
H13C H 1.280718 0.117233 0.322538 0.056 Uiso 1 1 calc R U . . .
C14 C 0.66975(11) 0.56006(14) 0.29610(3) 0.02235(17) Uani 1 1 d . . . . .
H14A H 0.692689 0.453310 0.279772 0.027 Uiso 1 1 calc R U . . .
H14B H 0.722568 0.655330 0.281341 0.027 Uiso 1 1 calc R U . . .
C15 C 0.49147(11) 0.59045(11) 0.29048(3) 0.01871(15) Uani 1 1 d . . . . .
C16 C 0.41864(11) 0.68882(12) 0.32239(3) 0.02151(16) Uani 1 1 d . . . . .
H16 H 0.481024 0.734915 0.348610 0.026 Uiso 1 1 calc R U . . .
C17 C 0.25513(12) 0.71963(13) 0.31594(4) 0.02376(17) Uani 1 1 d . . . . .
H17 H 0.206379 0.785259 0.337996 0.029 Uiso 1 1 calc R U . . .
C18 C 0.16307(12) 0.65463(14) 0.27734(4) 0.02700(19) Uani 1 1 d . . . . .
H18 H 0.051819 0.676743 0.272853 0.032 Uiso 1 1 calc R U . . .
C19 C 0.23433(13) 0.55732(16) 0.24538(4) 0.0293(2) Uani 1 1 d . . . . .
H19 H 0.171884 0.512977 0.218936 0.035 Uiso 1 1 calc R U . . .
C20 C 0.39783(13) 0.52466(14) 0.25213(3) 0.02436(18) Uani 1 1 d . . . . .
H20 H 0.445768 0.456883 0.230358 0.029 Uiso 1 1 calc R U . . .
C21 C 0.65725(12) 0.55084(12) 0.44615(3) 0.02170(16) Uani 1 1 d . . . . .
H21A H 0.631797 0.659123 0.430054 0.033 Uiso 1 1 calc R U . . .
H21B H 0.700638 0.574180 0.478136 0.033 Uiso 1 1 calc R U . . .
H21C H 0.560279 0.481839 0.445962 0.033 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 1.4352(12) . ?
O1 C7 1.4380(14) . ?
O2 C1 1.4195(12) . ?
O2 C8 1.4396(14) . ?
O3 C12 1.2097(12) . ?
O4 C12 1.3380(12) . ?
O4 C11 1.4603(12) . ?
O5 C10 1.2237(12) . ?
N1 C10 1.3668(13) . ?
N1 C4 1.4122(12) . ?
N1 C14 1.4554(13) . ?
C1 C6 1.5299(14) . ?
C1 C2 1.5375(13) . ?
C2 C3 1.5345(13) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C4 1.5141(13) . ?
C3 C21 1.5497(13) . ?
C3 C9 1.5650(13) . ?
C4 C5 1.3315(13) . ?
C5 C6 1.5072(14) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 C8 1.5376(17) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 C12 1.5178(14) . ?
C9 C10 1.5341(14) . ?
C9 H9 1.0000 . ?
C11 C13 1.5014(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.5150(14) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C20 1.3942(14) . ?
C15 C16 1.3988(13) . ?
C16 C17 1.3938(14) . ?
C16 H16 0.9500 . ?
C17 C18 1.3911(16) . ?
C17 H17 0.9500 . ?
C18 C19 1.3886(17) . ?
C18 H18 0.9500 . ?
C19 C20 1.3965(15) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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 C7 106.64(8) . . ?
C1 O2 C8 105.65(8) . . ?
C12 O4 C11 115.91(8) . . ?
C10 N1 C4 112.33(8) . . ?
C10 N1 C14 123.05(8) . . ?
C4 N1 C14 123.85(8) . . ?
O2 C1 O1 104.53(7) . . ?
O2 C1 C6 109.28(8) . . ?
O1 C1 C6 108.00(8) . . ?
O2 C1 C2 111.96(8) . . ?
O1 C1 C2 109.45(8) . . ?
C6 C1 C2 113.20(8) . . ?
C3 C2 C1 112.27(8) . . ?
C3 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 H2AB 109.2 . . ?
C1 C2 H2AB 109.2 . . ?
H2A C2 H2AB 107.9 . . ?
C4 C3 C2 109.00(7) . . ?
C4 C3 C21 109.97(7) . . ?
C2 C3 C21 113.06(7) . . ?
C4 C3 C9 101.35(7) . . ?
C2 C3 C9 115.67(7) . . ?
C21 C3 C9 107.12(7) . . ?
C5 C4 N1 127.36(8) . . ?
C5 C4 C3 125.36(8) . . ?
N1 C4 C3 107.23(7) . . ?
C4 C5 C6 121.76(8) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 115.21(8) . . ?
C5 C6 H6A 108.5 . . ?
C1 C6 H6A 108.5 . . ?
C5 C6 H6AB 108.5 . . ?
C1 C6 H6AB 108.5 . . ?
H6A C6 H6AB 107.5 . . ?
O1 C7 C8 104.85(8) . . ?
O1 C7 H7A 110.8 . . ?
C8 C7 H7A 110.8 . . ?
O1 C7 H7AB 110.8 . . ?
C8 C7 H7AB 110.8 . . ?
H7A C7 H7AB 108.9 . . ?
O2 C8 C7 103.80(8) . . ?
O2 C8 H8A 111.0 . . ?
C7 C8 H8A 111.0 . . ?
O2 C8 H8AB 111.0 . . ?
C7 C8 H8AB 111.0 . . ?
H8A C8 H8AB 109.0 . . ?
C12 C9 C10 110.56(7) . . ?
C12 C9 C3 112.05(8) . . ?
C10 C9 C3 102.84(7) . . ?
C12 C9 H9 110.4 . . ?
C10 C9 H9 110.4 . . ?
C3 C9 H9 110.4 . . ?
O5 C10 N1 125.83(9) . . ?
O5 C10 C9 126.17(9) . . ?
N1 C10 C9 107.99(8) . . ?
O4 C11 C13 106.97(9) . . ?
O4 C11 H11A 110.3 . . ?
C13 C11 H11A 110.3 . . ?
O4 C11 H11B 110.3 . . ?
C13 C11 H11B 110.3 . . ?
H11A C11 H11B 108.6 . . ?
O3 C12 O4 124.20(9) . . ?
O3 C12 C9 123.97(9) . . ?
O4 C12 C9 111.71(7) . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C15 113.23(7) . . ?
N1 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
N1 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C20 C15 C16 118.86(9) . . ?
C20 C15 C14 119.91(8) . . ?
C16 C15 C14 121.20(8) . . ?
C17 C16 C15 120.42(9) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C18 C17 C16 120.24(9) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C19 C18 C17 119.78(10) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 119.98(10) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C15 C20 C19 120.72(9) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C3 C21 H21A 109.5 . . ?
C3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_refine_diff_density_max         0.452
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.054

