# 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_sali
_database_code_depnum_ccdc_archive 'CCDC 1952993'
loop_
_audit_author_name
_audit_author_address
'Patrick McArdle'
;National University of Ireland, Galway
Republic of Ireland
;
_audit_update_record             
;
2019-11-22 deposited with the CCDC.	2019-12-10 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            'C15 H23 N O5'
_chemical_formula_weight         297.34
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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 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, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
_cell_length_a                   30.706(2)
_cell_length_b                   9.6913(7)
_cell_length_c                   11.0426(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3286.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296.4(8)
_cell_measurement_reflns_used    1617
_cell_measurement_theta_min      3.8410
_cell_measurement_theta_max      22.7720
_exptl_crystal_description       Parallelepiped
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.55958
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
crysalispro 1.171.40.14e (rigaku oxford diffraction, 2018)
empirical absorption correction using spherical harmonics,
 implemented in scale3 abspack scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296.4(8)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed x-ray tube'
_diffrn_measurement_device_type  'xcalibur, sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1048
_diffrn_reflns_number            10258
_diffrn_reflns_av_unetI/netI     0.0806
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.750
_diffrn_reflns_theta_max         29.121
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.767
_diffrn_reflns_point_group_measured_fraction_full 0.924
_reflns_number_total             6786
_reflns_number_gt                3283
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.576
_reflns_Friedel_fraction_max     0.637
_reflns_Friedel_fraction_full    0.830
_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       'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_cell_refinement       'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_data_reduction        'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEX - P. McArdle, J.Appl.Cryst.,1995,28,65-65.'
_computing_publication_material  
'Oscail - P. McArdle, J.Appl.Cryst.,2017,50,320-326.'
_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)+(0.0994P)²] 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_abs_structure_details 
;
 Flack x determined using 877 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         6786
_refine_ls_number_parameters     389
_refine_ls_number_restraints     255
_refine_ls_R_factor_all          0.1443
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_ref         0.2141
_refine_ls_wR_factor_gt          0.1680
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_restrained_S_all      0.950
_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 0.22627(13) 0.6248(4) 0.1381(4) 0.0775(12) Uani 1 1 d . . . . .
O43 O 0.28955(12) 0.9004(4) 0.0713(4) 0.0681(10) Uani 1 1 d . . . . .
O21 O 0.23293(14) 0.1593(4) 0.3857(4) 0.0776(12) Uani 1 1 d . . . . .
O41 O 0.30763(13) 1.0553(5) 0.2102(4) 0.0830(12) Uani 1 1 d . . . . .
N7 N 0.20818(15) 0.9647(4) -0.0213(4) 0.0648(12) Uani 1 1 d . . . . .
H7A H 0.195972 1.043764 0.001660 0.097 Uiso 1 1 calc R U . . .
H7B H 0.214267 0.968252 -0.100037 0.097 Uiso 1 1 calc R U . . .
H7C H 0.232641 0.951365 0.020347 0.097 Uiso 1 1 calc R U . . .
O3 O 0.25479(17) 0.7023(4) 0.3089(4) 0.0856(14) Uani 1 1 d . . . . .
H3 H 0.270529 0.634680 0.300246 0.128 Uiso 1 1 calc R U . . .
O50 O 0.34437(14) 0.7310(4) -0.0074(4) 0.0755(11) Uani 1 1 d . . . . .
H50 H 0.322689 0.779180 -0.017069 0.113 Uiso 1 1 calc R U . . .
O23 O 0.24043(13) 0.1991(5) 0.1904(3) 0.0736(12) Uani 1 1 d . . . . .
H23 H 0.264787 0.167018 0.201885 0.110 Uiso 1 1 calc R U . . .
N27 N 0.22425(14) 0.4283(5) 0.5276(4) 0.0663(12) Uani 1 1 d . . . . .
H27A H 0.224638 0.350925 0.570973 0.099 Uiso 1 1 calc R U . . .
H27B H 0.233076 0.498461 0.573502 0.099 Uiso 1 1 calc R U . . .
H27C H 0.242003 0.419546 0.464372 0.099 Uiso 1 1 calc R U . . .
O51 O 0.31438(17) 0.5295(5) 0.2667(4) 0.0994(15) Uani 1 1 d . . . . .
C2 C 0.22744(18) 0.7099(5) 0.2182(5) 0.0588(13) Uani 1 1 d . . . . .
O53 O 0.30363(16) 0.3979(5) 0.4222(5) 0.1067(17) Uani 1 1 d . . . . .
O60 O 0.3643(2) 0.2519(6) 0.5057(6) 0.1219(19) Uani 1 1 d . . . . .
H60 H 0.338678 0.264926 0.488581 0.183 Uiso 1 1 calc R U . . .
C25 C 0.16056(16) 0.3353(5) 0.4123(5) 0.0558(13) Uani 1 1 d . . . . .
H25 H 0.163487 0.250287 0.459590 0.067 Uiso 1 1 calc R U . . .
C4 C 0.19864(19) 0.8345(5) 0.2253(5) 0.0585(14) Uani 1 1 d . . . . .
H4A H 0.216782 0.915922 0.217453 0.070 Uiso 1 1 calc R U . . .
H4B H 0.185606 0.837020 0.305322 0.070 Uiso 1 1 calc R U . . .
C49 C 0.37379(17) 0.8001(5) 0.0604(5) 0.0543(12) Uani 1 1 d . . . . .
C22 C 0.22107(17) 0.2178(5) 0.2941(5) 0.0523(12) Uani 1 1 d . . . . .
C42 C 0.31654(16) 0.9579(6) 0.1397(5) 0.0547(12) Uani 1 1 d . . . . .
C44 C 0.36243(17) 0.9079(5) 0.1341(5) 0.0534(12) Uani 1 1 d . . . . .
C6 C 0.17755(17) 0.8488(5) 0.0023(5) 0.0599(13) Uani 1 1 d . . . . .
H6A H 0.191831 0.762440 -0.017378 0.072 Uiso 1 1 calc R U . . .
H6B H 0.152448 0.858256 -0.050351 0.072 Uiso 1 1 calc R U . . .
C24 C 0.18392(19) 0.3165(6) 0.2919(5) 0.0641(14) Uani 1 1 d . . . . .
H24A H 0.162944 0.285000 0.232348 0.077 Uiso 1 1 calc R U . . .
H24B H 0.194642 0.405657 0.265392 0.077 Uiso 1 1 calc R U . . .
C52 C 0.3277(2) 0.4444(6) 0.3409(5) 0.0643(14) Uani 1 1 d . . . . .
C54 C 0.37349(17) 0.4003(5) 0.3387(5) 0.0569(13) Uani 1 1 d . . . . .
C45 C 0.39480(19) 0.9742(7) 0.2019(6) 0.0766(17) Uani 1 1 d . . . . .
H45 H 0.387558 1.048373 0.251477 0.092 Uiso 1 1 calc R U . . .
C26 C 0.17989(18) 0.4548(5) 0.4848(6) 0.0684(15) Uani 1 1 d . . . . .
H26A H 0.180034 0.536874 0.434621 0.082 Uiso 1 1 calc R U . . .
H26B H 0.161340 0.472967 0.554123 0.082 Uiso 1 1 calc R U . . .
C11 C 0.0570(2) 0.6176(7) 0.1144(8) 0.107(3) Uani 1 1 d . . . . .
H11A H 0.073157 0.534969 0.097746 0.161 Uiso 1 1 calc R U . . .
H11B H 0.031661 0.620755 0.063520 0.161 Uiso 1 1 calc R U . . .
H11C H 0.048164 0.617962 0.197841 0.161 Uiso 1 1 calc R U . . .
C48 C 0.4174(2) 0.7555(7) 0.0534(6) 0.0791(17) Uani 1 1 d . . . . .
H48 H 0.425227 0.682820 0.002919 0.095 Uiso 1 1 calc R U . . .
C28 C 0.11226(19) 0.3654(7) 0.3937(7) 0.0843(19) Uani 1 1 d . . . . .
H28A H 0.100702 0.401534 0.469062 0.101 Uiso 1 1 calc R U . . .
H28B H 0.109692 0.437881 0.333532 0.101 Uiso 1 1 calc R U . . .
C59 C 0.3895(2) 0.3054(6) 0.4194(6) 0.0704(15) Uani 1 1 d . . . . .
C5 C 0.16229(17) 0.8439(5) 0.1321(5) 0.0571(13) Uani 1 1 d . . . . .
H5 H 0.147275 0.931400 0.147307 0.068 Uiso 1 1 calc R U . . .
C47 C 0.4484(2) 0.8229(9) 0.1236(8) 0.099(2) Uani 1 1 d . . . . .
H47 H 0.477234 0.793896 0.121256 0.119 Uiso 1 1 calc R U . . .
C46 C 0.4370(2) 0.9302(9) 0.1955(8) 0.105(2) Uani 1 1 d . . . . .
H46 H 0.458214 0.974664 0.241093 0.126 Uiso 1 1 calc R U . . .
C55 C 0.4016(2) 0.4539(8) 0.2532(6) 0.090(2) Uani 1 1 d . . . . .
H55 H 0.391248 0.517123 0.196752 0.108 Uiso 1 1 calc R U . . .
C58 C 0.4329(3) 0.2679(8) 0.4171(8) 0.102(2) Uani 1 1 d . . . . .
H58 H 0.443548 0.204654 0.473139 0.122 Uiso 1 1 calc R U . . .
C8 C 0.12837(17) 0.7294(6) 0.1522(6) 0.0731(16) Uani 1 1 d . . . . .
H8A H 0.141314 0.642636 0.127224 0.088 Uiso 1 1 calc R U . . .
H8B H 0.122800 0.722995 0.238433 0.088 Uiso 1 1 calc R U . . .
C56 C 0.4444(3) 0.4152(12) 0.2504(8) 0.136(4) Uani 1 1 d . . . . .
H56 H 0.463033 0.451451 0.192072 0.164 Uiso 1 1 calc R U . . .
C9 C 0.0855(2) 0.7433(7) 0.0893(8) 0.094(2) Uani 1 1 d . . . . .
H9 H 0.091364 0.745085 0.002070 0.113 Uiso 1 1 calc R U . . .
C57 C 0.4598(3) 0.3229(11) 0.3338(9) 0.127(3) Uani 1 1 d . . . . .
H57 H 0.489052 0.297987 0.332968 0.152 Uiso 1 1 calc R U . . .
C29 C 0.0847(3) 0.2503(11) 0.3558(11) 0.141(4) Uani 1 1 d . . . . .
H29 H 0.088890 0.205576 0.277046 0.169 Uiso 1 1 calc R U . A 1
C10 C 0.0608(3) 0.8712(9) 0.1196(13) 0.157(5) Uani 1 1 d . . . . .
H10A H 0.057998 0.879099 0.205873 0.235 Uiso 1 1 calc R U . . .
H10B H 0.032318 0.866659 0.083659 0.235 Uiso 1 1 calc R U . . .
H10C H 0.076014 0.950130 0.088577 0.235 Uiso 1 1 calc R U . . .
C30 C 0.0778(7) 0.159(2) 0.479(2) 0.143(7) Uiso 0.5 1 d . . P B 1
H30A H 0.098550 0.085163 0.480384 0.186 Uiso 0.5 1 calc R U P B 1
H30B H 0.048833 0.121936 0.479771 0.186 Uiso 0.5 1 calc R U P B 1
H30C H 0.081945 0.217043 0.548399 0.186 Uiso 0.5 1 calc R U P B 1
C30A C 0.0915(6) 0.1078(16) 0.4067(17) 0.111(5) Uiso 0.5 1 d . . P B 2
H30D H 0.115537 0.064538 0.366366 0.144 Uiso 0.5 1 calc R U P B 2
H30E H 0.065612 0.053854 0.394531 0.144 Uiso 0.5 1 calc R U P B 2
H30F H 0.097528 0.114236 0.491842 0.144 Uiso 0.5 1 calc R U P B 2
C31 C 0.0346(7) 0.342(3) 0.391(2) 0.157(8) Uiso 0.5 1 d . . P B 1
H31A H 0.040504 0.412775 0.449017 0.204 Uiso 0.5 1 calc R U P B 1
H31B H 0.013764 0.277995 0.423837 0.204 Uiso 0.5 1 calc R U P B 1
H31C H 0.023094 0.382082 0.318307 0.204 Uiso 0.5 1 calc R U P B 1
C31A C 0.0389(6) 0.2761(18) 0.3226(17) 0.110(5) Uiso 0.5 1 d . . P B 2
H31D H 0.020394 0.251795 0.389314 0.143 Uiso 0.5 1 calc R U P B 2
H31E H 0.031420 0.221208 0.253322 0.143 Uiso 0.5 1 calc R U P B 2
H31F H 0.035164 0.371998 0.303649 0.143 Uiso 0.5 1 calc R U P B 2
_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 1.210(6) . ?
O43 C42 1.252(6) . ?
O21 C22 1.216(6) . ?
O41 C42 1.254(6) . ?
N7 C6 1.488(6) . ?
O3 C2 1.310(7) . ?
O50 C49 1.351(6) . ?
O23 C22 1.302(6) . ?
N27 C26 1.464(7) . ?
O51 C52 1.233(7) . ?
C2 C4 1.498(7) . ?
O53 C52 1.248(7) . ?
O60 C59 1.332(8) . ?
C25 C24 1.521(7) . ?
C25 C28 1.525(7) . ?
C25 C26 1.528(7) . ?
C4 C5 1.521(7) . ?
C49 C44 1.370(7) . ?
C49 C48 1.408(7) . ?
C22 C24 1.489(7) . ?
C42 C44 1.491(7) . ?
C44 C45 1.401(8) . ?
C6 C5 1.508(8) . ?
C52 C54 1.469(8) . ?
C54 C59 1.372(8) . ?
C54 C55 1.380(8) . ?
C45 C46 1.365(8) . ?
C11 C9 1.526(9) . ?
C48 C47 1.391(10) . ?
C28 C29 1.462(11) . ?
C59 C58 1.381(9) . ?
C5 C8 1.538(7) . ?
C47 C46 1.354(10) . ?
C55 C56 1.369(11) . ?
C58 C57 1.346(11) . ?
C8 C9 1.493(8) . ?
C56 C57 1.367(12) . ?
C9 C10 1.493(11) . ?
C29 C31A 1.474(17) . ?
C29 C30A 1.505(17) . ?
C29 C30 1.63(2) . ?
C29 C31 1.82(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
O1 C2 O3 122.7(5) . . ?
O1 C2 C4 124.8(5) . . ?
O3 C2 C4 112.6(5) . . ?
C24 C25 C28 111.4(5) . . ?
C24 C25 C26 111.5(5) . . ?
C28 C25 C26 107.7(5) . . ?
C2 C4 C5 116.5(4) . . ?
O50 C49 C44 122.5(5) . . ?
O50 C49 C48 116.9(5) . . ?
C44 C49 C48 120.6(6) . . ?
O21 C22 O23 122.0(5) . . ?
O21 C22 C24 122.8(5) . . ?
O23 C22 C24 115.1(5) . . ?
O43 C42 O41 124.4(5) . . ?
O43 C42 C44 117.1(5) . . ?
O41 C42 C44 118.4(5) . . ?
C49 C44 C45 119.1(5) . . ?
C49 C44 C42 120.9(5) . . ?
C45 C44 C42 120.0(5) . . ?
N7 C6 C5 112.8(4) . . ?
C22 C24 C25 115.1(5) . . ?
O51 C52 O53 121.6(6) . . ?
O51 C52 C54 120.1(6) . . ?
O53 C52 C54 118.3(6) . . ?
C59 C54 C55 118.2(6) . . ?
C59 C54 C52 121.8(6) . . ?
C55 C54 C52 120.0(6) . . ?
C46 C45 C44 120.1(6) . . ?
N27 C26 C25 113.5(4) . . ?
C47 C48 C49 118.4(6) . . ?
C29 C28 C25 117.1(6) . . ?
O60 C59 C54 121.1(6) . . ?
O60 C59 C58 118.1(7) . . ?
C54 C59 C58 120.7(7) . . ?
C6 C5 C4 114.6(4) . . ?
C6 C5 C8 111.7(5) . . ?
C4 C5 C8 110.9(5) . . ?
C46 C47 C48 120.7(6) . . ?
C47 C46 C45 121.1(7) . . ?
C56 C55 C54 120.9(7) . . ?
C57 C58 C59 120.0(8) . . ?
C9 C8 C5 117.7(5) . . ?
C57 C56 C55 119.7(8) . . ?
C10 C9 C8 114.8(7) . . ?
C10 C9 C11 109.2(6) . . ?
C8 C9 C11 110.5(6) . . ?
C58 C57 C56 120.5(8) . . ?
C28 C29 C31A 119.6(11) . . ?
C28 C29 C30A 120.9(9) . . ?
C31A C29 C30A 112.3(12) . . ?
C28 C29 C30 104.4(10) . . ?
C28 C29 C31 93.3(10) . . ?
C30 C29 C31 88.6(12) . . ?
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
O1 C2 C4 C5 7.2(8) . . . . ?
O3 C2 C4 C5 -173.2(5) . . . . ?
O50 C49 C44 C45 179.8(5) . . . . ?
C48 C49 C44 C45 0.4(8) . . . . ?
O50 C49 C44 C42 -2.1(7) . . . . ?
C48 C49 C44 C42 178.5(5) . . . . ?
O43 C42 C44 C49 -2.5(7) . . . . ?
O41 C42 C44 C49 178.7(5) . . . . ?
O43 C42 C44 C45 175.5(5) . . . . ?
O41 C42 C44 C45 -3.3(8) . . . . ?
O21 C22 C24 C25 -2.2(8) . . . . ?
O23 C22 C24 C25 178.4(5) . . . . ?
C28 C25 C24 C22 -148.0(5) . . . . ?
C26 C25 C24 C22 91.7(6) . . . . ?
O51 C52 C54 C59 -179.7(5) . . . . ?
O53 C52 C54 C59 3.1(8) . . . . ?
O51 C52 C54 C55 -0.2(8) . . . . ?
O53 C52 C54 C55 -177.3(6) . . . . ?
C49 C44 C45 C46 -0.8(10) . . . . ?
C42 C44 C45 C46 -178.9(6) . . . . ?
C24 C25 C26 N27 -67.7(6) . . . . ?
C28 C25 C26 N27 169.9(5) . . . . ?
O50 C49 C48 C47 -178.9(6) . . . . ?
C44 C49 C48 C47 0.5(9) . . . . ?
C24 C25 C28 C29 73.6(8) . . . . ?
C26 C25 C28 C29 -164.0(7) . . . . ?
C55 C54 C59 O60 178.6(6) . . . . ?
C52 C54 C59 O60 -1.8(9) . . . . ?
C55 C54 C59 C58 1.9(9) . . . . ?
C52 C54 C59 C58 -178.6(6) . . . . ?
N7 C6 C5 C4 -56.6(6) . . . . ?
N7 C6 C5 C8 176.2(4) . . . . ?
C2 C4 C5 C6 -61.1(6) . . . . ?
C2 C4 C5 C8 66.6(6) . . . . ?
C49 C48 C47 C46 -1.1(11) . . . . ?
C48 C47 C46 C45 0.7(13) . . . . ?
C44 C45 C46 C47 0.3(12) . . . . ?
C59 C54 C55 C56 -1.1(10) . . . . ?
C52 C54 C55 C56 179.3(7) . . . . ?
O60 C59 C58 C57 -177.9(8) . . . . ?
C54 C59 C58 C57 -1.1(11) . . . . ?
C6 C5 C8 C9 -65.4(7) . . . . ?
C4 C5 C8 C9 165.4(6) . . . . ?
C54 C55 C56 C57 -0.4(14) . . . . ?
C5 C8 C9 C10 -58.7(9) . . . . ?
C5 C8 C9 C11 177.2(6) . . . . ?
C59 C58 C57 C56 -0.5(14) . . . . ?
C55 C56 C57 C58 1.3(15) . . . . ?
C25 C28 C29 C31A -172.9(10) . . . . ?
C25 C28 C29 C30A 39.0(15) . . . . ?
C25 C28 C29 C30 76.4(12) . . . . ?
C25 C28 C29 C31 165.8(10) . . . . ?
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
N7 H7A O50 0.89 2.20 3.060(6) 163.0 3 yes
N7 H7B O1 0.89 2.41 2.850(6) 110.7 3 yes
N7 H7B O51 0.89 2.12 2.867(6) 140.4 3 yes
N7 H7C O43 0.89 1.90 2.770(6) 165.1 . yes
O3 H3 O51 0.82 1.73 2.524(6) 162.8 . yes
O50 H50 O43 0.82 1.84 2.507(5) 138.2 . yes
O23 H23 O41 0.82 1.71 2.500(5) 162.3 1_545 yes
N27 H27A O3 0.89 2.06 2.910(6) 160.2 3_546 yes
N27 H27B O21 0.89 1.93 2.767(6) 156.1 3_556 yes
N27 H27C O53 0.89 1.96 2.717(7) 142.0 . yes
O60 H60 O53 0.82 1.83 2.515(7) 139.9 . yes
C6 H6A O1 0.97 2.42 3.033(7) 121.0 . yes
C24 H24A O50 0.97 2.55 3.364(7) 141.6 3_545 yes
C26 H26A O60 0.97 2.58 3.186(8) 121.0 3_556 yes
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_oxal
_database_code_depnum_ccdc_archive 'CCDC 1952994'
loop_
_audit_author_name
_audit_author_address
'Patrick McArdle'
;National University of Ireland, Galway
Republic of Ireland
;
_audit_update_record             
;
2019-11-22 deposited with the CCDC.	2019-12-10 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            'C9 H18 N O4'
_chemical_formula_weight         204.24
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           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                   11.7250(10)
_cell_length_b                   6.1271(4)
_cell_length_c                   16.0527(15)
_cell_angle_alpha                90
_cell_angle_beta                 99.628(9)
_cell_angle_gamma                90
_cell_volume                     1136.99(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    294.0(3)
_cell_measurement_reflns_used    2083
_cell_measurement_theta_min      3.9270
_cell_measurement_theta_max      28.9310
_exptl_crystal_description       Parallelepiped
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.51318
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
crysalispro 1.171.40.14e (rigaku oxford diffraction, 2018)
empirical absorption correction using spherical harmonics,
 implemented in scale3 abspack scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294.0(3)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed x-ray tube'
_diffrn_measurement_device_type  'xcalibur, sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1048
_diffrn_reflns_number            5043
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.525
_diffrn_reflns_theta_max         29.202
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.886
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.886
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2580
_reflns_number_gt                2271
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_max     0.781
_reflns_Friedel_fraction_full    0.976
_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       'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_cell_refinement       'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_data_reduction        'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEX - P. McArdle, J.Appl.Cryst.,1995,28,65-65.'
_computing_publication_material  
'Oscail - P. McArdle, J.Appl.Cryst.,2017,50,320-326.'
_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)+(0.0580P)²+0.1627P] 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_abs_structure_details 
;
 Flack x determined using 867 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(6)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2580
_refine_ls_number_parameters     131
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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
O6 O 0.76550(14) 0.4115(3) 0.39987(11) 0.0384(4) Uani 1 1 d . . . . .
O7 O 0.60064(15) 0.5027(3) 0.31699(12) 0.0433(5) Uani 1 1 d . . . . .
H7 H 0.590118 0.575496 0.357906 0.065 Uiso 1 1 calc R U . . .
O12 O 0.58214(19) 1.1073(3) 0.44762(13) 0.0518(5) Uani 1 1 d . . . . .
O11 O 0.5520(2) 0.7499(4) 0.43454(15) 0.0621(6) Uani 1 1 d . . . . .
N1 N 0.8304(2) -0.0502(3) 0.43217(13) 0.0407(5) Uani 1 1 d . . . . .
H1A H 0.881161 0.055607 0.448640 0.061 Uiso 1 1 calc R U . . .
H1B H 0.848786 -0.167887 0.464090 0.061 Uiso 1 1 calc R U . . .
H1C H 0.759782 -0.005415 0.437619 0.061 Uiso 1 1 calc R U . . .
C5 C 0.69346(19) 0.3796(3) 0.33805(15) 0.0305(5) Uani 1 1 d . . . . .
C14 C 0.53881(18) 0.9348(4) 0.46580(14) 0.0310(5) Uani 1 1 d . . . . .
C2 C 0.8327(2) -0.1049(4) 0.34262(17) 0.0383(6) Uani 1 1 d . . . . .
H2A H 0.772215 -0.210851 0.324211 0.046 Uiso 1 1 calc R U . . .
H2B H 0.906110 -0.174121 0.339083 0.046 Uiso 1 1 calc R U . . .
C3 C 0.8166(2) 0.0873(4) 0.28167(15) 0.0323(5) Uani 1 1 d . . . . .
H3 H 0.876981 0.195290 0.300766 0.039 Uiso 1 1 calc R U . . .
C8 C 0.8346(2) 0.0004(5) 0.19533(17) 0.0448(6) Uani 1 1 d . . . . .
H8A H 0.904763 -0.086408 0.203482 0.054 Uiso 1 1 calc R U . . .
H8B H 0.770856 -0.096665 0.174465 0.054 Uiso 1 1 calc R U . . .
C4 C 0.6983(2) 0.1990(4) 0.27604(17) 0.0392(5) Uani 1 1 d . . . . .
H4A H 0.676061 0.257244 0.219452 0.047 Uiso 1 1 calc R U . . .
H4B H 0.641507 0.089480 0.284367 0.047 Uiso 1 1 calc R U . . .
C9 C 0.8436(3) 0.1704(7) 0.1268(2) 0.0671(10) Uani 1 1 d . . . . .
H9 H 0.771237 0.253478 0.116404 0.081 Uiso 1 1 calc R U . . .
C11 C 0.8573(6) 0.0540(11) 0.0460(3) 0.122(2) Uani 1 1 d . . . . .
H11A H 0.926224 -0.033469 0.055611 0.182 Uiso 1 1 calc R U . . .
H11B H 0.863025 0.159517 0.002724 0.182 Uiso 1 1 calc R U . . .
H11C H 0.791443 -0.038096 0.028487 0.182 Uiso 1 1 calc R U . . .
C10 C 0.9425(6) 0.3294(10) 0.1535(3) 0.118(2) Uani 1 1 d . . . . .
H10A H 0.929539 0.407137 0.203014 0.177 Uiso 1 1 calc R U . . .
H10B H 0.946352 0.431100 0.108596 0.177 Uiso 1 1 calc R U . . .
H10C H 1.014010 0.250302 0.165862 0.177 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
O6 C5 1.207(3) . ?
O7 C5 1.321(3) . ?
O12 C14 1.229(3) . ?
O11 C14 1.259(3) . ?
N1 C2 1.481(3) . ?
C5 C4 1.496(3) . ?
C14 C14 1.539(4) 2_656 ?
C2 C3 1.523(3) . ?
C3 C8 1.532(3) . ?
C3 C4 1.536(3) . ?
C8 C9 1.532(5) . ?
C9 C11 1.511(6) . ?
C9 C10 1.520(7) . ?
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
O6 C5 O7 123.5(2) . . ?
O6 C5 C4 124.6(2) . . ?
O7 C5 C4 111.9(2) . . ?
O12 C14 O11 126.6(2) . . ?
O12 C14 C14 119.13(15) . 2_656 ?
O11 C14 C14 114.28(16) . 2_656 ?
N1 C2 C3 115.36(19) . . ?
C2 C3 C8 106.95(19) . . ?
C2 C3 C4 113.3(2) . . ?
C8 C3 C4 111.2(2) . . ?
C9 C8 C3 116.8(3) . . ?
C5 C4 C3 115.1(2) . . ?
C11 C9 C10 111.1(4) . . ?
C11 C9 C8 109.0(4) . . ?
C10 C9 C8 111.9(3) . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C8 174.1(2) . . . . ?
N1 C2 C3 C4 -63.0(3) . . . . ?
C2 C3 C8 C9 -169.7(3) . . . . ?
C4 C3 C8 C9 66.1(3) . . . . ?
O6 C5 C4 C3 -15.3(4) . . . . ?
O7 C5 C4 C3 164.3(2) . . . . ?
C2 C3 C4 C5 89.4(3) . . . . ?
C8 C3 C4 C5 -150.1(2) . . . . ?
C3 C8 C9 C11 -178.2(3) . . . . ?
C3 C8 C9 C10 58.5(4) . . . . ?
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_oxal_lt
_database_code_depnum_ccdc_archive 'CCDC 1967509'
loop_
_audit_author_name
_audit_author_address
'Patrick McArdle'
; National University of Ireland
Republic of Ireland
;
_audit_update_record             
;
2019-11-22 deposited with the CCDC.	2019-12-10 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            'C18 H36 N2 O8'
_chemical_formula_weight         408.49
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           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                   11.5328(10)
_cell_length_b                   6.1123(5)
_cell_length_c                   16.0138(14)
_cell_angle_alpha                90
_cell_angle_beta                 99.780(9)
_cell_angle_gamma                90
_cell_volume                     1112.44(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    150.0(1)
_cell_measurement_reflns_used    1292
_cell_measurement_theta_min      4.3600
_cell_measurement_theta_max      29.1780
_exptl_crystal_description       Parallelepiped
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.74806
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
crysalispro 1.171.40.14e (rigaku oxford diffraction, 2018)
empirical absorption correction using spherical harmonics,
 implemented in scale3 abspack scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed x-ray tube'
_diffrn_measurement_device_type  'xcalibur, sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1048
_diffrn_reflns_number            2690
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.599
_diffrn_reflns_theta_max         29.069
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.617
_diffrn_reflns_point_group_measured_fraction_full 0.745
_reflns_number_total             1838
_reflns_number_gt                1720
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.301
_reflns_Friedel_fraction_max     0.313
_reflns_Friedel_fraction_full    0.435
_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       'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_cell_refinement       'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_data_reduction        'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEX - P. McArdle, J.Appl.Cryst.,1995,28,65-65.'
_computing_publication_material  
'Oscail - P. McArdle, J.Appl.Cryst.,2017,50,320-326.'
_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)+(0.0575P)²+0.2355P] 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_abs_structure_details 
;
 Flack x determined using 388 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.5(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         1838
_refine_ls_number_parameters     131
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1026
_refine_ls_wR_factor_gt          0.0997
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.083
_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
O6 O 0.76793(13) 0.4112(3) 0.39852(9) 0.0207(3) Uani 1 1 d . . . . .
O7 O 0.60062(13) 0.5067(3) 0.31433(10) 0.0233(4) Uani 1 1 d . . . . .
H7 H 0.592614 0.585389 0.354427 0.035 Uiso 1 1 calc R U . . .
O12 O 0.58480(14) 1.1123(3) 0.44745(10) 0.0235(4) Uani 1 1 d . . . . .
O11 O 0.55119(14) 0.7534(3) 0.43288(11) 0.0275(4) Uani 1 1 d . . . . .
N1 N 0.83253(16) -0.0448(3) 0.43329(11) 0.0222(4) Uani 1 1 d . . . . .
H1A H 0.884770 0.061180 0.448512 0.033 Uiso 1 1 calc R U . . .
H1B H 0.851332 -0.161066 0.466277 0.033 Uiso 1 1 calc R U . . .
H1C H 0.761159 0.001971 0.438853 0.033 Uiso 1 1 calc R U . . .
C5 C 0.69380(17) 0.3793(4) 0.33605(14) 0.0181(4) Uani 1 1 d . . . . .
C14 C 0.53948(17) 0.9377(4) 0.46491(12) 0.0175(4) Uani 1 1 d . . . . .
C2 C 0.83309(19) -0.1058(4) 0.34345(14) 0.0206(5) Uani 1 1 d . . . . .
H2A H 0.770630 -0.210995 0.326244 0.025 Uiso 1 1 calc R U . . .
H2B H 0.907050 -0.178037 0.340104 0.025 Uiso 1 1 calc R U . . .
C3 C 0.81742(18) 0.0826(4) 0.28074(13) 0.0184(4) Uani 1 1 d . . . . .
H3 H 0.879545 0.190530 0.298607 0.022 Uiso 1 1 calc R U . . .
C8 C 0.8338(2) -0.0110(4) 0.19493(14) 0.0247(5) Uani 1 1 d . . . . .
H8A H 0.905362 -0.097499 0.203416 0.030 Uiso 1 1 calc R U . . .
H8B H 0.768923 -0.109800 0.175805 0.030 Uiso 1 1 calc R U . . .
C4 C 0.69753(18) 0.1970(4) 0.27438(14) 0.0212(5) Uani 1 1 d . . . . .
H4A H 0.675353 0.254524 0.217455 0.025 Uiso 1 1 calc R U . . .
H4B H 0.639201 0.088602 0.282884 0.025 Uiso 1 1 calc R U . . .
C9 C 0.8409(2) 0.1530(6) 0.12405(15) 0.0367(7) Uani 1 1 d . . . . .
H9 H 0.766541 0.233850 0.112733 0.044 Uiso 1 1 calc R U . . .
C11 C 0.8556(3) 0.0307(8) 0.04421(19) 0.0652(12) Uani 1 1 d . . . . .
H11A H 0.927986 -0.050169 0.054113 0.098 Uiso 1 1 calc R U . . .
H11B H 0.857189 0.133269 -0.000987 0.098 Uiso 1 1 calc R U . . .
H11C H 0.790910 -0.068403 0.028925 0.098 Uiso 1 1 calc R U . . .
C10 C 0.9401(4) 0.3168(7) 0.1482(2) 0.0632(11) Uani 1 1 d . . . . .
H10A H 0.924473 0.404675 0.194696 0.095 Uiso 1 1 calc R U . . .
H10B H 0.945518 0.409266 0.100537 0.095 Uiso 1 1 calc R U . . .
H10C H 1.013019 0.239898 0.164556 0.095 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
O6 C5 1.216(3) . ?
O7 C5 1.325(3) . ?
O12 C14 1.241(3) . ?
O11 C14 1.255(3) . ?
N1 C2 1.487(3) . ?
C5 C4 1.495(3) . ?
C14 C14 1.562(4) 2_656 ?
C2 C3 1.519(3) . ?
C3 C8 1.530(3) . ?
C3 C4 1.537(3) . ?
C8 C9 1.527(4) . ?
C9 C11 1.515(4) . ?
C9 C10 1.520(5) . ?
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
O6 C5 O7 123.2(2) . . ?
O6 C5 C4 124.60(19) . . ?
O7 C5 C4 112.20(18) . . ?
O12 C14 O11 126.98(19) . . ?
O12 C14 C14 118.78(12) . 2_656 ?
O11 C14 C14 114.23(13) . 2_656 ?
N1 C2 C3 115.47(18) . . ?
C2 C3 C8 106.94(18) . . ?
C2 C3 C4 113.16(18) . . ?
C8 C3 C4 110.95(17) . . ?
C9 C8 C3 116.9(2) . . ?
C5 C4 C3 114.95(17) . . ?
C11 C9 C10 110.6(3) . . ?
C11 C9 C8 109.3(3) . . ?
C10 C9 C8 112.1(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
N1 C2 C3 C8 174.05(17) . . . . ?
N1 C2 C3 C4 -63.5(2) . . . . ?
C2 C3 C8 C9 -170.88(19) . . . . ?
C4 C3 C8 C9 65.3(3) . . . . ?
O6 C5 C4 C3 -15.3(3) . . . . ?
O7 C5 C4 C3 163.68(19) . . . . ?
C2 C3 C4 C5 88.4(2) . . . . ?
C8 C3 C4 C5 -151.42(19) . . . . ?
C3 C8 C9 C11 -179.3(2) . . . . ?
C3 C8 C9 C10 57.6(3) . . . . ?
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
O7 H7 O11 0.82 1.75 2.563(2) 170.7 . yes
N1 H1A O11 0.89 2.30 3.112(3) 151.7 3_545 yes
N1 H1A O11 0.89 2.25 2.956(3) 136.2 4_646 yes
N1 H1B O12 0.89 2.01 2.886(3) 169.7 4_636 yes
N1 H1C O12 0.89 2.17 3.059(2) 177.8 1_545 yes
C2 H2A O6 0.97 2.59 3.207(3) 122.0 1_545 yes
C2 H2A O7 0.97 2.59 3.548(3) 167.8 1_545 yes
C2 H2B O7 0.97 2.60 3.271(3) 126.8 3_545 yes
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.228
_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_sali_lt
_database_code_depnum_ccdc_archive 'CCDC 1967510'
loop_
_audit_author_name
_audit_author_address
'Patrick McArdle'
; National University of Ireland
Republic of Ireland
;
_audit_update_record             
;
2019-11-22 deposited with the CCDC.	2019-12-10 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            'C15 H23 N O5'
_chemical_formula_weight         297.34
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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 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, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
_cell_length_a                   9.5719(7)
_cell_length_b                   30.798(2)
_cell_length_c                   10.9331(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3223.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    153.0(7)
_cell_measurement_reflns_used    2071
_cell_measurement_theta_min      3.8790
_cell_measurement_theta_max      28.2400
_exptl_crystal_description       Parallelepiped
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.60087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
crysalispro 1.171.40.14e (rigaku oxford diffraction, 2018)
empirical absorption correction using spherical harmonics,
 implemented in scale3 abspack scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153.0(7)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed x-ray tube'
_diffrn_measurement_device_type  'xcalibur, sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1048
_diffrn_reflns_number            9425
_diffrn_reflns_av_unetI/netI     0.0824
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.727
_diffrn_reflns_theta_max         29.134
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.701
_diffrn_reflns_point_group_measured_fraction_full 0.845
_reflns_number_total             6070
_reflns_number_gt                4640
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.451
_reflns_Friedel_fraction_max     0.496
_reflns_Friedel_fraction_full    0.647
_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       'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_cell_refinement       'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_data_reduction        'crysalispro 1.171.40.14e (rigaku od, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEX - P. McArdle, J.Appl.Cryst.,1995,28,65-65.'
_computing_publication_material  
'Oscail - P. McArdle, J.Appl.Cryst.,2017,50,320-326.'
_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)+(0.0619P)²+0.1321P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1069 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.8(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         6070
_refine_ls_number_parameters     401
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0638
_refine_ls_wR_factor_ref         0.1609
_refine_ls_wR_factor_gt          0.1403
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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
O53 O -0.1058(3) 0.21080(9) 0.0732(3) 0.0335(7) Uani 1 1 d . . . . .
O21 O 0.1575(3) 0.26875(10) 0.3866(3) 0.0347(7) Uani 1 1 d . . . . .
O3 O 0.6948(3) 0.24358(10) 0.3119(3) 0.0366(7) Uani 1 1 d D . . . .
O1 O 0.6168(3) 0.27371(9) 0.1404(3) 0.0353(7) Uani 1 1 d . . . . .
O51 O 0.0563(3) 0.19347(9) 0.2110(3) 0.0395(7) Uani 1 1 d . . . . .
O60 O -0.2722(3) 0.15466(10) -0.0074(3) 0.0382(7) Uani 1 1 d D . . . .
O23 O 0.1951(3) 0.26188(10) 0.1867(3) 0.0368(7) Uani 1 1 d D . . . .
O41 O 0.5205(4) 0.18508(11) 0.2633(3) 0.0444(8) Uani 1 1 d . . . . .
N7 N 0.9610(3) 0.29218(10) -0.0185(3) 0.0280(7) Uani 1 1 d . . . . .
H7A H 1.041379 0.303989 0.005228 0.036 Uiso 1 1 calc R U . . .
H7B H 0.964734 0.286322 -0.098172 0.036 Uiso 1 1 calc R U . . .
H7C H 0.946340 0.267728 0.022940 0.036 Uiso 1 1 calc R U . . .
O50 O 0.2455(4) 0.13088(12) 0.5090(4) 0.0499(9) Uani 1 1 d D . . . .
N27 N 0.4270(3) 0.27432(10) 0.5256(3) 0.0282(7) Uani 1 1 d . . . . .
H27A H 0.350734 0.274328 0.572172 0.037 Uiso 1 1 calc R U . . .
H27B H 0.499185 0.264490 0.568833 0.037 Uiso 1 1 calc R U . . .
H27C H 0.413391 0.257229 0.461079 0.037 Uiso 1 1 calc R U . . .
O43 O 0.3822(4) 0.19395(10) 0.4232(3) 0.0494(9) Uani 1 1 d . . . . .
C2 C 0.7035(4) 0.27179(12) 0.2210(4) 0.0254(8) Uani 1 1 d . . . . .
C4 C 0.8297(4) 0.30094(13) 0.2307(4) 0.0263(8) Uani 1 1 d . . . . .
H4A H 0.912534 0.283010 0.222795 0.034 Uiso 1 1 calc R U . . .
H4B H 0.830962 0.313378 0.312198 0.034 Uiso 1 1 calc R U . . .
C5 C 0.8412(4) 0.33828(12) 0.1381(4) 0.0245(8) Uani 1 1 d . . . . .
H5 H 0.929978 0.353093 0.153992 0.032 Uiso 1 1 calc R U . . .
C6 C 0.8444(4) 0.32317(13) 0.0057(4) 0.0265(8) Uani 1 1 d . . . . .
H6A H 0.756334 0.309243 -0.013925 0.034 Uiso 1 1 calc R U . . .
H6B H 0.854583 0.348219 -0.047378 0.034 Uiso 1 1 calc R U . . .
C8 C 0.7243(4) 0.37182(12) 0.1576(4) 0.0313(9) Uani 1 1 d . . . . .
H8A H 0.636294 0.358481 0.134630 0.041 Uiso 1 1 calc R U . . .
H8B H 0.719203 0.378363 0.244280 0.041 Uiso 1 1 calc R U . . .
C9 C 0.7379(5) 0.41459(13) 0.0881(4) 0.0398(11) Uani 1 1 d . . . . .
H9 H 0.737199 0.408060 0.000420 0.052 Uiso 1 1 calc R U . . .
C10 C 0.8716(5) 0.43822(16) 0.1169(6) 0.0657(18) Uani 1 1 d . . . . .
H10A H 0.871193 0.466002 0.077043 0.085 Uiso 1 1 calc R U . . .
H10B H 0.949578 0.421484 0.088164 0.085 Uiso 1 1 calc R U . . .
H10C H 0.879193 0.442249 0.203668 0.085 Uiso 1 1 calc R U . . .
C11 C 0.6128(5) 0.44311(15) 0.1160(5) 0.0474(13) Uani 1 1 d . . . . .
H11A H 0.612562 0.450466 0.201280 0.062 Uiso 1 1 calc R U . . .
H11B H 0.528494 0.427750 0.096169 0.062 Uiso 1 1 calc R U . . .
H11C H 0.618076 0.469173 0.068015 0.062 Uiso 1 1 calc R U . . .
C22 C 0.2141(4) 0.28052(12) 0.2931(4) 0.0267(8) Uani 1 1 d . . . . .
C24 C 0.3117(4) 0.31913(13) 0.2894(4) 0.0315(9) Uani 1 1 d . . . . .
H24A H 0.273440 0.340676 0.234077 0.041 Uiso 1 1 calc R U . . .
H24B H 0.400886 0.309809 0.256392 0.041 Uiso 1 1 calc R U . . .
C25 C 0.3367(4) 0.34041(12) 0.4137(4) 0.0265(9) Uani 1 1 d . . . . .
H25 H 0.251552 0.337319 0.462654 0.034 Uiso 1 1 calc R U . . .
C26 C 0.4568(4) 0.31954(13) 0.4833(4) 0.0288(9) Uani 1 1 d . . . . .
H26A H 0.538636 0.319048 0.430963 0.037 Uiso 1 1 calc R U . . .
H26B H 0.478680 0.337369 0.553852 0.037 Uiso 1 1 calc R U . . .
C28 C 0.3690(4) 0.38908(13) 0.4001(4) 0.0339(10) Uani 1 1 d . . . . .
H28A H 0.398633 0.400075 0.479124 0.044 Uiso 1 1 calc R U . . .
H28B H 0.447082 0.392256 0.344353 0.044 Uiso 1 1 calc R U . . .
C29 C 0.2498(5) 0.41733(14) 0.3543(5) 0.0500(13) Uani 1 1 d . . . . .
H29 H 0.228803 0.408340 0.270327 0.065 Uiso 1 1 calc R U . . .
C30 C 0.1187(6) 0.4127(2) 0.4274(7) 0.094(3) Uani 1 1 d . . . . .
H30A H 0.076230 0.385124 0.409887 0.122 Uiso 1 1 calc R U . . .
H30B H 0.055101 0.435585 0.406355 0.122 Uiso 1 1 calc R U . . .
H30C H 0.140507 0.414307 0.513015 0.122 Uiso 1 1 calc R U . . .
C31 C 0.2961(8) 0.46495(16) 0.3501(8) 0.099(3) Uani 1 1 d . . . . .
H31A H 0.222484 0.482344 0.316172 0.129 Uiso 1 1 calc R U . . .
H31B H 0.378104 0.467549 0.300036 0.129 Uiso 1 1 calc R U . . .
H31C H 0.316808 0.474774 0.431436 0.129 Uiso 1 1 calc R U . . .
C42 C 0.4347(4) 0.17080(13) 0.3406(4) 0.0297(9) Uani 1 1 d . . . . .
C44 C 0.3938(4) 0.12437(12) 0.3342(4) 0.0248(8) Uani 1 1 d . . . . .
C45 C 0.4505(5) 0.09730(15) 0.2459(4) 0.0401(11) Uani 1 1 d . . . . .
H45 H 0.512439 0.108638 0.188622 0.052 Uiso 1 1 calc R U . . .
C46 C 0.4163(7) 0.05361(16) 0.2417(5) 0.0664(19) Uani 1 1 d . . . . .
H46 H 0.453970 0.035891 0.181209 0.086 Uiso 1 1 calc R U . . .
C47 C 0.3260(7) 0.03642(15) 0.3277(5) 0.0598(16) Uani 1 1 d . . . . .
H47 H 0.304938 0.006949 0.326019 0.078 Uiso 1 1 calc R U . . .
C48 C 0.2673(5) 0.06233(15) 0.4152(5) 0.0435(11) Uani 1 1 d . . . . .
H48 H 0.205256 0.050723 0.471839 0.057 Uiso 1 1 calc R U . . .
C49 C 0.3016(4) 0.10671(14) 0.4187(4) 0.0313(9) Uani 1 1 d . . . . .
C52 C -0.0419(4) 0.18388(13) 0.1409(4) 0.0284(9) Uani 1 1 d . . . . .
C54 C -0.0891(4) 0.13740(12) 0.1352(4) 0.0256(8) Uani 1 1 d . . . . .
C55 C -0.0185(5) 0.10579(14) 0.2026(4) 0.0376(10) Uani 1 1 d . . . . .
H55 H 0.056164 0.113709 0.252213 0.049 Uiso 1 1 calc R U . . .
C56 C -0.0594(5) 0.06245(15) 0.1960(5) 0.0495(13) Uani 1 1 d . . . . .
H56 H -0.012056 0.041466 0.240962 0.064 Uiso 1 1 calc R U . . .
C57 C -0.1709(5) 0.05067(14) 0.1222(5) 0.0449(12) Uani 1 1 d . . . . .
H57 H -0.198577 0.021754 0.118394 0.058 Uiso 1 1 calc R U . . .
C58 C -0.2409(5) 0.08132(15) 0.0548(4) 0.0375(10) Uani 1 1 d . . . . .
H58 H -0.314752 0.073058 0.004609 0.049 Uiso 1 1 calc R U . . .
C59 C -0.2011(4) 0.12508(13) 0.0614(4) 0.0283(9) Uani 1 1 d . . . . .
H23 H 0.147(4) 0.2376(10) 0.211(4) 0.040(13) Uiso 1 1 d D . . . .
H3 H 0.622(6) 0.225(2) 0.309(7) 0.13(3) Uiso 1 1 d D . . . .
H50 H 0.281(7) 0.1577(12) 0.500(7) 0.11(3) Uiso 1 1 d D . . . .
H60 H -0.221(5) 0.1779(13) 0.009(6) 0.08(2) Uiso 1 1 d D . . . .
_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
O53 C52 1.269(5) . ?
O21 C22 1.212(4) . ?
O3 C2 1.322(5) . ?
O3 H3 0.90(2) . ?
O1 C2 1.212(5) . ?
O51 C52 1.249(5) . ?
O60 C59 1.364(5) . ?
O60 H60 0.89(2) . ?
O23 C22 1.310(5) . ?
O23 H23 0.92(2) . ?
O41 C42 1.258(5) . ?
N7 C6 1.492(5) . ?
N7 H7A 0.8900 . ?
N7 H7B 0.8900 . ?
N7 H7C 0.8900 . ?
O50 C49 1.348(5) . ?
O50 H50 0.90(2) . ?
N27 C26 1.495(5) . ?
N27 H27A 0.8900 . ?
N27 H27B 0.8900 . ?
N27 H27C 0.8900 . ?
O43 C42 1.256(5) . ?
C2 C4 1.509(5) . ?
C4 C5 1.536(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.521(5) . ?
C5 C8 1.538(5) . ?
C5 H5 0.9800 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 C9 1.526(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.505(7) . ?
C9 C11 1.516(6) . ?
C9 H9 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C22 C24 1.513(5) . ?
C24 C25 1.527(6) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.521(5) . ?
C25 C28 1.538(5) . ?
C25 H25 0.9800 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C28 C29 1.519(6) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C30 1.495(7) . ?
C29 C31 1.533(7) . ?
C29 H29 0.9800 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C42 C44 1.484(5) . ?
C44 C45 1.387(6) . ?
C44 C49 1.388(6) . ?
C45 C46 1.386(7) . ?
C45 H45 0.9300 . ?
C46 C47 1.383(8) . ?
C46 H46 0.9300 . ?
C47 C48 1.366(7) . ?
C47 H47 0.9300 . ?
C48 C49 1.406(6) . ?
C48 H48 0.9300 . ?
C52 C54 1.502(5) . ?
C54 C59 1.394(5) . ?
C54 C55 1.396(6) . ?
C55 C56 1.393(6) . ?
C55 H55 0.9300 . ?
C56 C57 1.386(7) . ?
C56 H56 0.9300 . ?
C57 C58 1.372(7) . ?
C57 H57 0.9300 . ?
C58 C59 1.403(6) . ?
C58 H58 0.9300 . ?
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 O3 H3 116(5) . . ?
C59 O60 H60 99(4) . . ?
C22 O23 H23 100(3) . . ?
C6 N7 H7A 109.5 . . ?
C6 N7 H7B 109.5 . . ?
H7A N7 H7B 109.5 . . ?
C6 N7 H7C 109.5 . . ?
H7A N7 H7C 109.5 . . ?
H7B N7 H7C 109.5 . . ?
C49 O50 H50 106(5) . . ?
C26 N27 H27A 109.5 . . ?
C26 N27 H27B 109.5 . . ?
H27A N27 H27B 109.5 . . ?
C26 N27 H27C 109.5 . . ?
H27A N27 H27C 109.5 . . ?
H27B N27 H27C 109.5 . . ?
O1 C2 O3 122.3(4) . . ?
O1 C2 C4 124.8(4) . . ?
O3 C2 C4 112.9(3) . . ?
C2 C4 C5 117.2(3) . . ?
C2 C4 H4A 108.0 . . ?
C5 C4 H4A 108.0 . . ?
C2 C4 H4B 108.0 . . ?
C5 C4 H4B 108.0 . . ?
H4A C4 H4B 107.2 . . ?
C6 C5 C4 113.6(3) . . ?
C6 C5 C8 110.6(3) . . ?
C4 C5 C8 111.1(3) . . ?
C6 C5 H5 107.1 . . ?
C4 C5 H5 107.1 . . ?
C8 C5 H5 107.1 . . ?
N7 C6 C5 112.3(3) . . ?
N7 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
N7 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
C9 C8 C5 116.6(3) . . ?
C9 C8 H8A 108.1 . . ?
C5 C8 H8A 108.1 . . ?
C9 C8 H8B 108.1 . . ?
C5 C8 H8B 108.1 . . ?
H8A C8 H8B 107.3 . . ?
C10 C9 C11 110.5(4) . . ?
C10 C9 C8 112.7(4) . . ?
C11 C9 C8 109.4(4) . . ?
C10 C9 H9 108.0 . . ?
C11 C9 H9 108.0 . . ?
C8 C9 H9 108.0 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O21 C22 O23 123.8(3) . . ?
O21 C22 C24 122.2(4) . . ?
O23 C22 C24 114.0(3) . . ?
C22 C24 C25 114.2(3) . . ?
C22 C24 H24A 108.7 . . ?
C25 C24 H24A 108.7 . . ?
C22 C24 H24B 108.7 . . ?
C25 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
C26 C25 C24 112.5(3) . . ?
C26 C25 C28 108.0(3) . . ?
C24 C25 C28 111.4(3) . . ?
C26 C25 H25 108.3 . . ?
C24 C25 H25 108.3 . . ?
C28 C25 H25 108.3 . . ?
N27 C26 C25 113.9(3) . . ?
N27 C26 H26A 108.8 . . ?
C25 C26 H26A 108.8 . . ?
N27 C26 H26B 108.8 . . ?
C25 C26 H26B 108.8 . . ?
H26A C26 H26B 107.7 . . ?
C29 C28 C25 116.1(4) . . ?
C29 C28 H28A 108.3 . . ?
C25 C28 H28A 108.3 . . ?
C29 C28 H28B 108.3 . . ?
C25 C28 H28B 108.3 . . ?
H28A C28 H28B 107.4 . . ?
C30 C29 C28 113.5(4) . . ?
C30 C29 C31 110.5(5) . . ?
C28 C29 C31 109.9(5) . . ?
C30 C29 H29 107.5 . . ?
C28 C29 H29 107.5 . . ?
C31 C29 H29 107.5 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O43 C42 O41 123.1(4) . . ?
O43 C42 C44 118.4(4) . . ?
O41 C42 C44 118.5(4) . . ?
C45 C44 C49 118.5(4) . . ?
C45 C44 C42 120.5(4) . . ?
C49 C44 C42 120.9(4) . . ?
C46 C45 C44 120.9(5) . . ?
C46 C45 H45 119.5 . . ?
C44 C45 H45 119.5 . . ?
C47 C46 C45 119.8(5) . . ?
C47 C46 H46 120.1 . . ?
C45 C46 H46 120.1 . . ?
C48 C47 C46 120.6(4) . . ?
C48 C47 H47 119.7 . . ?
C46 C47 H47 119.7 . . ?
C47 C48 C49 119.4(5) . . ?
C47 C48 H48 120.3 . . ?
C49 C48 H48 120.3 . . ?
O50 C49 C44 121.6(4) . . ?
O50 C49 C48 117.7(4) . . ?
C44 C49 C48 120.7(4) . . ?
O51 C52 O53 124.5(4) . . ?
O51 C52 C54 118.5(4) . . ?
O53 C52 C54 117.0(3) . . ?
C59 C54 C55 119.2(4) . . ?
C59 C54 C52 121.0(4) . . ?
C55 C54 C52 119.8(4) . . ?
C56 C55 C54 120.3(4) . . ?
C56 C55 H55 119.8 . . ?
C54 C55 H55 119.8 . . ?
C57 C56 C55 119.8(4) . . ?
C57 C56 H56 120.1 . . ?
C55 C56 H56 120.1 . . ?
C58 C57 C56 120.6(4) . . ?
C58 C57 H57 119.7 . . ?
C56 C57 H57 119.7 . . ?
C57 C58 C59 120.0(4) . . ?
C57 C58 H58 120.0 . . ?
C59 C58 H58 120.0 . . ?
O60 C59 C54 121.4(4) . . ?
O60 C59 C58 118.5(4) . . ?
C54 C59 C58 120.0(4) . . ?
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
O1 C2 C4 C5 5.8(6) . . . . ?
O3 C2 C4 C5 -173.2(3) . . . . ?
C2 C4 C5 C6 -59.4(4) . . . . ?
C2 C4 C5 C8 66.0(4) . . . . ?
C4 C5 C6 N7 -57.1(4) . . . . ?
C8 C5 C6 N7 177.2(3) . . . . ?
C6 C5 C8 C9 -63.8(4) . . . . ?
C4 C5 C8 C9 169.1(3) . . . . ?
C5 C8 C9 C10 -57.9(5) . . . . ?
C5 C8 C9 C11 178.8(4) . . . . ?
O21 C22 C24 C25 2.4(6) . . . . ?
O23 C22 C24 C25 -178.8(3) . . . . ?
C22 C24 C25 C26 87.6(4) . . . . ?
C22 C24 C25 C28 -151.1(3) . . . . ?
C24 C25 C26 N27 -68.6(4) . . . . ?
C28 C25 C26 N27 168.2(3) . . . . ?
C26 C25 C28 C29 -169.0(4) . . . . ?
C24 C25 C28 C29 67.1(5) . . . . ?
C25 C28 C29 C30 53.6(7) . . . . ?
C25 C28 C29 C31 178.0(5) . . . . ?
O43 C42 C44 C45 -179.0(4) . . . . ?
O41 C42 C44 C45 0.9(6) . . . . ?
O43 C42 C44 C49 -1.1(6) . . . . ?
O41 C42 C44 C49 178.7(4) . . . . ?
C49 C44 C45 C46 0.0(7) . . . . ?
C42 C44 C45 C46 177.9(5) . . . . ?
C44 C45 C46 C47 -1.0(9) . . . . ?
C45 C46 C47 C48 1.6(9) . . . . ?
C46 C47 C48 C49 -1.2(8) . . . . ?
C45 C44 C49 O50 178.2(4) . . . . ?
C42 C44 C49 O50 0.3(6) . . . . ?
C45 C44 C49 C48 0.4(6) . . . . ?
C42 C44 C49 C48 -177.5(4) . . . . ?
C47 C48 C49 O50 -177.7(4) . . . . ?
C47 C48 C49 C44 0.2(7) . . . . ?
O51 C52 C54 C59 178.0(4) . . . . ?
O53 C52 C54 C59 -2.0(6) . . . . ?
O51 C52 C54 C55 -3.3(6) . . . . ?
O53 C52 C54 C55 176.7(4) . . . . ?
C59 C54 C55 C56 0.1(7) . . . . ?
C52 C54 C55 C56 -178.6(4) . . . . ?
C54 C55 C56 C57 -0.1(8) . . . . ?
C55 C56 C57 C58 0.5(8) . . . . ?
C56 C57 C58 C59 -0.9(7) . . . . ?
C55 C54 C59 O60 -179.1(4) . . . . ?
C52 C54 C59 O60 -0.4(6) . . . . ?
C55 C54 C59 C58 -0.5(6) . . . . ?
C52 C54 C59 C58 178.2(4) . . . . ?
C57 C58 C59 O60 179.6(4) . . . . ?
C57 C58 C59 C54 0.9(7) . . . . ?
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
N7 H7A O60 0.89 2.19 3.047(4) 160.8 4_655 yes
N7 H7B O1 0.89 2.40 2.849(4) 111.7 4 yes
N7 H7B O41 0.89 2.08 2.824(4) 140.7 4 yes
N7 H7C O53 0.89 1.90 2.774(4) 165.3 1_655 yes
N27 H27A O3 0.89 2.03 2.899(5) 163.4 4_456 yes
N27 H27B O21 0.89 1.89 2.748(4) 160.4 4_556 yes
N27 H27C O43 0.89 2.01 2.751(4) 139.2 . yes
C6 H6A O1 0.97 2.41 3.040(5) 121.8 . yes
C24 H24A O60 0.97 2.52 3.287(5) 135.9 4 yes
C26 H26A O50 0.97 2.59 3.159(5) 117.3 4_556 yes
O23 H23 O51 0.92(2) 1.61(3) 2.505(4) 164(5) . yes
O3 H3 O41 0.90(2) 1.65(4) 2.512(4) 161(8) . yes
O50 H50 O43 0.90(2) 1.70(4) 2.523(5) 151(7) . yes
O60 H60 O53 0.89(2) 1.65(3) 2.511(4) 162(6) . yes
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.062
