# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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. 
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data_Compound_2
_database_code_depnum_ccdc_archive 'CCDC 1589955'
_audit_update_record             
;
2017-12-08 deposited with the CCDC.
2018-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            'Aculeatine A'
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H22 N2 O4, C H4 O'
_chemical_formula_sum            'C22 H26 N2 O5'
_chemical_formula_weight         398.45

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           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   23.52(2)
_cell_length_b                   5.994(5)
_cell_length_c                   15.843(13)
_cell_angle_alpha                90
_cell_angle_beta                 112.574(17)
_cell_angle_gamma                90
_cell_volume                     2063(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    9974
_cell_measurement_theta_min      5.871
_cell_measurement_theta_max      67.530

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.749
_shelx_estimated_absorpt_T_min   0.865
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9168
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans, φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11796
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         5.854
_diffrn_reflns_theta_max         65.556
_diffrn_reflns_theta_full        65.556
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.959
_reflns_number_total             3416
_reflns_number_gt                3283
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.783
_reflns_Friedel_fraction_max     0.940
_reflns_Friedel_fraction_full    0.941

_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       'APEX2 (Bruker, 2012)'
_computing_cell_refinement       'SAINT (Bruker, 2012)'
_computing_data_reduction        'SAINT (Bruker, 2012)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick 2015a)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    'DIAMOND 4.3.1 (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2015b)'


_refine_special_details          
;
 Refinement of F² against ALL reflections. The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0393P)²+0.5585P] 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_abs_structure_details 
;
 Flack x determined using 1433 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3416
_refine_ls_number_parameters     276
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0667
_refine_ls_wR_factor_gt          0.0658
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_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 0.65940(5) 0.4912(2) 0.55654(9) 0.0217(3) Uani 1 1 d . . . . .
O2 O 0.67925(6) 0.8600(2) 0.56768(10) 0.0264(3) Uani 1 1 d . . . . .
H2 H 0.7028(12) 0.837(5) 0.5388(19) 0.040 Uiso 1 1 d . U . . .
O3 O 0.47820(5) 0.7223(2) 0.59769(9) 0.0200(3) Uani 1 1 d . . . . .
O4 O 0.52224(6) 0.1513(2) 0.61967(9) 0.0209(3) Uani 1 1 d . . . . .
H4 H 0.5044(11) 0.026(5) 0.6077(16) 0.031 Uiso 1 1 d . U . . .
N1 N 0.71816(7) 0.3323(3) 0.86983(11) 0.0250(4) Uani 1 1 d . . . . .
N2 N 0.56792(6) 0.5381(2) 0.61928(10) 0.0159(3) Uani 1 1 d . . . . .
H2A H 0.5843(10) 0.411(4) 0.6252(15) 0.024 Uiso 1 1 d . U . . .
C1 C 0.65075(8) 0.6794(3) 0.57837(12) 0.0178(4) Uani 1 1 d . . . . .
C2 C 0.60560(8) 0.7325(3) 0.62335(13) 0.0165(4) Uani 1 1 d . . . . .
H2B H 0.577933 0.855237 0.587888 0.020 Uiso 1 1 calc R U . . .
C3 C 0.63959(7) 0.8138(3) 0.72349(12) 0.0178(4) Uani 1 1 d . . . . .
H3A H 0.663460 0.949729 0.723413 0.021 Uiso 1 1 calc R U . . .
H3B H 0.608733 0.854029 0.749298 0.021 Uiso 1 1 calc R U . . .
C4 C 0.68242(8) 0.6407(3) 0.78355(13) 0.0168(4) Uani 1 1 d . . . . .
C5 C 0.74738(8) 0.6176(3) 0.80238(13) 0.0202(4) Uani 1 1 d . . . . .
C6 C 0.79002(9) 0.7470(4) 0.78148(14) 0.0297(5) Uani 1 1 d . . . . .
H6 H 0.777470 0.879763 0.746491 0.036 Uiso 1 1 calc R U . . .
C7 C 0.85081(10) 0.6769(5) 0.81295(16) 0.0433(6) Uani 1 1 d . . . . .
H7 H 0.880125 0.763759 0.799645 0.052 Uiso 1 1 calc R U . . .
C8 C 0.86993(9) 0.4796(5) 0.86421(16) 0.0443(7) Uani 1 1 d . . . . .
H8 H 0.911734 0.434408 0.883813 0.053 Uiso 1 1 calc R U . . .
C9 C 0.82937(9) 0.3510(4) 0.88650(15) 0.0359(5) Uani 1 1 d . . . . .
H9 H 0.842422 0.218204 0.921340 0.043 Uiso 1 1 calc R U . . .
C10 C 0.76795(8) 0.4230(3) 0.85592(13) 0.0239(4) Uani 1 1 d . . . . .
C11 C 0.72095(11) 0.1406(3) 0.92782(15) 0.0360(5) Uani 1 1 d . . . . .
H11A H 0.679396 0.104221 0.923939 0.054 Uiso 1 1 calc R U . . .
H11B H 0.747203 0.176076 0.991262 0.054 Uiso 1 1 calc R U . . .
H11C H 0.738118 0.012401 0.907256 0.054 Uiso 1 1 calc R U . . .
C12 C 0.66742(8) 0.4651(3) 0.82618(13) 0.0209(4) Uani 1 1 d . . . . .
H12 H 0.627510 0.438323 0.825783 0.025 Uiso 1 1 calc R U . . .
C13 C 0.50817(7) 0.5468(3) 0.60666(12) 0.0152(4) Uani 1 1 d . . . . .
C14 C 0.47683(7) 0.3204(3) 0.60060(12) 0.0169(4) Uani 1 1 d . . . . .
H14 H 0.446512 0.299651 0.536475 0.020 Uiso 1 1 calc R U . . .
C15 C 0.44174(7) 0.3112(3) 0.66470(13) 0.0199(4) Uani 1 1 d . . . . .
H15A H 0.409851 0.429231 0.646612 0.024 Uiso 1 1 calc R U . . .
H15B H 0.420496 0.165551 0.656916 0.024 Uiso 1 1 calc R U . . .
C16 C 0.48240(8) 0.3414(3) 0.76430(13) 0.0210(4) Uani 1 1 d . . . . .
C17 C 0.51729(9) 0.1636(3) 0.81604(14) 0.0249(4) Uani 1 1 d . . . . .
H17 H 0.515975 0.022724 0.787880 0.030 Uiso 1 1 calc R U . . .
C18 C 0.55377(9) 0.1913(4) 0.90803(15) 0.0324(5) Uani 1 1 d . . . . .
H18 H 0.577221 0.069519 0.942311 0.039 Uiso 1 1 calc R U . . .
C19 C 0.55616(10) 0.3964(4) 0.95023(15) 0.0375(5) Uani 1 1 d . . . . .
H19 H 0.580949 0.415055 1.013255 0.045 Uiso 1 1 calc R U . . .
C20 C 0.52212(11) 0.5731(4) 0.89961(16) 0.0377(5) Uani 1 1 d . . . . .
H20 H 0.523651 0.713660 0.928079 0.045 Uiso 1 1 calc R U . . .
C21 C 0.48570(9) 0.5465(3) 0.80747(15) 0.0278(4) Uani 1 1 d . . . . .
H21 H 0.462772 0.669634 0.773457 0.033 Uiso 1 1 calc R U . . .
O5 O 0.74323(6) 0.7709(2) 0.46886(10) 0.0268(3) Uani 1 1 d . . . . .
H5 H 0.7733(12) 0.847(5) 0.4755(18) 0.040 Uiso 1 1 d . U . . .
C22 C 0.70283(11) 0.7748(5) 0.37583(17) 0.0507(7) Uani 1 1 d . . . . .
H22A H 0.726833 0.770439 0.337153 0.076 Uiso 1 1 calc R U . . .
H22B H 0.678190 0.911660 0.363293 0.076 Uiso 1 1 calc R U . . .
H22C H 0.675487 0.644859 0.362577 0.076 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 1.220(2) . ?
O2 C1 1.318(2) . ?
O2 H2 0.85(3) . ?
O3 C13 1.244(2) . ?
O4 C14 1.418(2) . ?
O4 H4 0.85(3) . ?
N1 C12 1.379(3) . ?
N1 C10 1.383(3) . ?
N1 C11 1.457(3) . ?
N2 C13 1.343(3) . ?
N2 C2 1.450(2) . ?
N2 H2A 0.84(3) . ?
C1 C2 1.522(3) . ?
C2 C3 1.556(3) . ?
C2 H2B 1.0000 . ?
C3 C4 1.503(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C12 1.368(3) . ?
C4 C5 1.447(3) . ?
C5 C6 1.404(3) . ?
C5 C10 1.414(3) . ?
C6 C7 1.387(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.407(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.374(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.404(3) . ?
C9 H9 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12 0.9500 . ?
C13 C14 1.530(3) . ?
C14 C15 1.536(3) . ?
C14 H14 1.0000 . ?
C15 C16 1.509(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C21 1.395(3) . ?
C16 C17 1.401(3) . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.390(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.389(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
O5 C22 1.414(3) . ?
O5 H5 0.81(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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 O2 H2 113.9(19) . . ?
C14 O4 H4 108.6(17) . . ?
C12 N1 C10 108.42(17) . . ?
C12 N1 C11 126.31(18) . . ?
C10 N1 C11 125.05(18) . . ?
C13 N2 C2 124.25(15) . . ?
C13 N2 H2A 117.2(15) . . ?
C2 N2 H2A 118.5(15) . . ?
O1 C1 O2 125.09(17) . . ?
O1 C1 C2 123.26(15) . . ?
O2 C1 C2 111.65(15) . . ?
N2 C2 C1 109.60(15) . . ?
N2 C2 C3 111.29(15) . . ?
C1 C2 C3 111.41(15) . . ?
N2 C2 H2B 108.1 . . ?
C1 C2 H2B 108.1 . . ?
C3 C2 H2B 108.1 . . ?
C4 C3 C2 112.74(15) . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C12 C4 C5 106.08(16) . . ?
C12 C4 C3 127.31(16) . . ?
C5 C4 C3 126.47(16) . . ?
C6 C5 C10 119.09(18) . . ?
C6 C5 C4 133.81(18) . . ?
C10 C5 C4 107.06(17) . . ?
C7 C6 C5 118.7(2) . . ?
C7 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C6 C7 C8 121.3(2) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C7 121.4(2) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 117.6(2) . . ?
C8 C9 H9 121.2 . . ?
C10 C9 H9 121.2 . . ?
N1 C10 C9 130.3(2) . . ?
N1 C10 C5 107.70(16) . . ?
C9 C10 C5 122.0(2) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4 C12 N1 110.73(17) . . ?
C4 C12 H12 124.6 . . ?
N1 C12 H12 124.6 . . ?
O3 C13 N2 124.38(16) . . ?
O3 C13 C14 120.32(15) . . ?
N2 C13 C14 115.28(15) . . ?
O4 C14 C13 108.37(14) . . ?
O4 C14 C15 112.68(14) . . ?
C13 C14 C15 111.01(15) . . ?
O4 C14 H14 108.2 . . ?
C13 C14 H14 108.2 . . ?
C15 C14 H14 108.2 . . ?
C16 C15 C14 113.65(15) . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C21 C16 C17 118.27(19) . . ?
C21 C16 C15 120.78(17) . . ?
C17 C16 C15 120.95(18) . . ?
C18 C17 C16 120.7(2) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 120.4(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 119.4(2) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C21 120.5(2) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C20 C21 C16 120.79(19) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?
C22 O5 H5 109.1(19) . . ?
O5 C22 H22A 109.5 . . ?
O5 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O5 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
O2 H2 O5 0.85(3) 1.76(3) 2.609(2) 172(3) . yes
O4 H4 O3 0.85(3) 1.91(3) 2.744(3) 169(2) 1_545 yes
N2 H2A O4 0.84(3) 2.11(2) 2.557(3) 112.6(18) . yes
C2 H2B O4 1.00 2.37 3.172(3) 136.4 1_565 yes
C14 H14 O1 1.00 2.62 3.375(3) 132.0 2_656 yes
O5 H5 O1 0.81(3) 2.03(3) 2.803(3) 158(3) 4_656 yes

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.053


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_chemical_compound_source        'Endophytic Fungus Aspergillus aculeatus'
