# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_hari_se_sx
_database_code_depnum_ccdc_archive 'CCDC 2207173'
loop_
_audit_author_name
_audit_author_address
'Geoffrey Jameson'
;School of Natural Sciences, Massey University
New Zealand
;
_audit_update_record             
;
2022-09-14 deposited with the CCDC.	2023-05-23 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_hari_se_sx          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.887 Why?
RESPONSE: High mosaicity cuasing reflection overlap and consequent elimination of reflections. Main aim of structure determination was establishing connectivity and stereochemistry at C5 knowing configuration of beta-D-2'-deoxyribose. Accomplished.
;
_vrf_PLAT241_hari_se_sx          
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of       C13T Check
RESPONSE: Loose crystal packing and room temperature data (XStream died) led to very high torsional motion of the benzyl group and one of the toluoyl groups. 
;
_vrf_PLAT242_hari_se_sx          
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of       C11T Check
RESPONSE: Loose crystal packing and room temperature data (XStream died) led to very high torsional motion of the benzyl group and one of the toluoyl groups. 
;
_vrf_PLAT315_hari_se_sx          
;
PROBLEM: Singly Bonded Carbon Detected (H-atoms Missing).       C16T Check
RESPONSE: Riding refinkment of this methyl group was unstable and therefore eliminated.
;
_vrf_PLAT340_hari_se_sx          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01634 Ang.
RESPONSE: Overall high atomic displacement parameters, exacerbated by high torsional motions of benzyl group and one toluoyl group. 
;
_vrf_PLAT911_hari_se_sx          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.595        276 Report
RESPONSE: Eliminated 4 reflections with very poor agreement between Fcalc and Fobs (see Plat029).
;
# Added during the CSD deposition process: Wednesday 14 September 2022 10:34 AM
# end Validation Reply Form

_audit_creation_date             2022-09-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
1-[2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-(R)-5-benzyloxyazepan-2-one
_chemical_formula_moiety         'C34 H34 N O7'
_chemical_formula_sum            'C34 H34 N O7'
_chemical_formula_weight         568.62
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'I 1 2 1'
_space_group_name_Hall           'I 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   19.200(2)
_cell_length_b                   5.3821(5)
_cell_length_c                   32.153(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.636(9)
_cell_angle_gamma                90
_cell_volume                     3284.9(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4610
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.554
_cell_measurement_theta_min      5.567
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.877
_exptl_absorpt_coefficient_mu    0.655
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_absorpt_special_details   
;
Note that the experimental absorption process corrects not only for absorption but for mis-alignment.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'flattened needle'
_exptl_crystal_F_000             1284
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0735
_diffrn_reflns_Laue_measured_fraction_full 0.887
_diffrn_reflns_Laue_measured_fraction_max 0.887
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            6980
_diffrn_reflns_point_group_measured_fraction_full 0.735
_diffrn_reflns_point_group_measured_fraction_max 0.735
_diffrn_reflns_theta_full        66.554
_diffrn_reflns_theta_max         66.554
_diffrn_reflns_theta_min         5.567
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Image plate'
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.887
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measurement_device_type  'Rigaku Spider/Rapide'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  'Rigaku VariMax-HF Confocal Optical System'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_source                   'Rigaku MM007 microfocus roating anode/'
_reflns_Friedel_coverage         0.485
_reflns_Friedel_fraction_full    0.543
_reflns_Friedel_fraction_max     0.543
_reflns_number_gt                1774
_reflns_number_total             4270
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'FSProcess in Process-Auto (Rigaku, 1998)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'FSProcess in Process-Auto (Rigaku, 1998)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 505 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         4270
_refine_ls_number_restraints     187
_refine_ls_R_factor_all          0.1303
_refine_ls_R_factor_gt           0.0693
_refine_ls_restrained_S_all      0.917
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1410P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1842
_refine_ls_wR_factor_ref         0.2434
_refine_special_details          
;
Absolute structure was weakly determined by Flack x (-0.2(3) and Hooft  y (0.0(2) parameters. The expected beta-D-2-deoxyribose was observed, establishing the S-diasteromer at nucleobase atom C5.
Data were collected at 293 K due to breakdown of XStream. As a result, and also due to loose packing, one benzyl group suffers very high torsional motions. Tight restrainsts were applied to interatomic distances, planarity, and atomic displacement parameters for the toluoyl and benzyl groups. The methyl hydrogens on one toluoyl group were omitted as their positions were unstable under riding refinement.     

;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C22T-C28T = C27T-C25T = C24T-C23T
 1.392 with sigma of 0.01
 C2T-C7T = C6T-C5T = C4T-C3T
 1.392 with sigma of 0.01
 C15T-C12T = C17T-C13T = C18T-C14T
 2.784 with sigma of 0.01
 C12T-C18T = C17T-C15T = C14T-C13T
 1.392 with sigma of 0.01
 C15T-C12T
 2.784 with sigma of 0.01
 C17T-C13T
 2.784 with sigma of 0.01
 C18T-C14T
 2.784 with sigma of 0.01
3. Restrained planarity
 O3', O11T, C11T, C12T
 with sigma of 0.1
 C21T, C22T, C28T, C27T, C25T, C26T, C24T, C23T
 with sigma of 0.1
 C22T, C21T, O21T, O5'
 with sigma of 0.1
 C11T, C12T, C13T, C14T, C15T, C16T, C17T, C18T
 with sigma of 0.1
 C1T, C2T, C7T, C6T, C5T, C4T, C3T
 with sigma of 0.1
 C1', N1, C2, O2, C3
 with sigma of 0.1
4. Rigid bond restraints
 C11T, C12T, C18T, C17T, C15T, C16T, C14T, C13T
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C1T, C2T, C7T, C6T, C5T, C4T, C3T
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
C12T \\sim C18T \\sim C17T \\sim C15T \\sim C16T \\sim C14T \\sim C13T: within
2A with sigma of 0.1 and sigma for terminal atoms of 0.1
C1T \\sim C2T \\sim C7T \\sim C6T \\sim C5T \\sim C4T \\sim C3T: within 2A with
sigma of 0.1 and sigma for terminal atoms of 0.1
Uanis(C16T) \\sim Ueq, Uanis(C18T) \\sim Ueq, Uanis(C13T) \\sim Ueq,
Uanis(C14T) \\sim Ueq, Uanis(C17T) \\sim Ueq, Uanis(C15T) \\sim Ueq: with sigma
of 0.1 and sigma for terminal atoms of 0.2
6.a Ternary CH refined with riding coordinates:
 C1'(H1'), C4'(H4'), C3'(H3'), C5(H5)
6.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C7(H7A,H7B), C5'(H5'A,H5'B), C6(H6A,H6B), C2'(H2'A,H2'B), C4(H4A,
 H4B), C1T(H1TA,H1TB)
6.c Aromatic/amide H refined with riding coordinates:
 C28T(H28T), C23T(H23T), C24T(H24T), C27T(H27T), C7T(H7T), C3T(H3T),
 C17T(H17T), C6T(H6T), C13T(H13T), C18T(H18T), C4T(H4T), C5T(H5T), C14T(H14T)
6.d Idealised Me refined as rotating group:
 C26T(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
O5' O 0.6981(2) 0.6398(11) 0.30230(14) 0.1004(16) Uani 1 1 d . . . . .
O21T O 0.7898(3) 0.4840(13) 0.27587(18) 0.1130(19) Uani 1 1 d . . . . .
O1' O 0.5754(3) 0.3627(12) 0.31910(19) 0.1097(18) Uani 1 1 d . . . . .
O5 O 0.7258(3) 0.3326(14) 0.48472(19) 0.131(2) Uani 1 1 d . . . . .
O3' O 0.4764(3) 0.7811(15) 0.2723(2) 0.136(2) Uani 1 1 d . . . . .
C21T C 0.7675(4) 0.6230(18) 0.2990(3) 0.093(2) Uani 1 1 d . . . . .
N1 N 0.5768(3) 0.4283(14) 0.3905(2) 0.111(2) Uani 1 1 d . . . . .
C1' C 0.5433(4) 0.510(2) 0.3477(3) 0.102(3) Uani 1 1 d . . . . .
H1' H 0.492620 0.476136 0.344033 0.122 Uiso 1 1 calc R . . . .
O2 O 0.4743(3) 0.303(2) 0.40662(18) 0.177(3) Uani 1 1 d . . . . .
C4' C 0.5795(4) 0.506(2) 0.2806(3) 0.104(3) Uani 1 1 d . . . . .
H4' H 0.547830 0.432018 0.257143 0.125 Uiso 1 1 calc R . . . .
C22T C 0.8115(3) 0.7903(16) 0.3278(2) 0.091(2) Uani 1 1 d D . . . .
C3 C 0.5723(4) 0.251(2) 0.4592(3) 0.121(3) Uani 1 1 d . . . . .
H3A H 0.608771 0.130210 0.456262 0.146 Uiso 1 1 calc R . . . .
H3B H 0.537259 0.168308 0.473200 0.146 Uiso 1 1 calc R . . . .
C7 C 0.6564(3) 0.4424(18) 0.4009(2) 0.101(3) Uani 1 1 d . . . . .
H7A H 0.674318 0.278988 0.409515 0.121 Uiso 1 1 calc R . . . .
H7B H 0.675324 0.486908 0.375558 0.121 Uiso 1 1 calc R . . . .
C2 C 0.5392(4) 0.326(2) 0.4175(3) 0.119(3) Uani 1 1 d . . . . .
C5' C 0.6528(4) 0.4939(19) 0.2716(2) 0.109(3) Uani 1 1 d . . . . .
H5'A H 0.668763 0.322631 0.272757 0.130 Uiso 1 1 calc R . . . .
H5'B H 0.654901 0.557441 0.243628 0.130 Uiso 1 1 calc R . . . .
C25T C 0.9000(4) 1.113(2) 0.3824(3) 0.122(3) Uani 1 1 d D . . . .
C3' C 0.5521(4) 0.760(2) 0.2903(3) 0.107(3) Uani 1 1 d . . . . .
H3' H 0.579963 0.892367 0.280029 0.129 Uiso 1 1 calc R . . . .
C28T C 0.7848(4) 0.9780(19) 0.3518(3) 0.113(3) Uani 1 1 d D . . . .
H28T H 0.736342 0.992861 0.350758 0.136 Uiso 1 1 calc R . . . .
C23T C 0.8850(4) 0.7638(18) 0.3324(2) 0.108(3) Uani 1 1 d D . . . .
H23T H 0.904952 0.636745 0.318558 0.130 Uiso 1 1 calc R . . . .
C24T C 0.9269(4) 0.927(2) 0.3575(3) 0.135(4) Uani 1 1 d D . . . .
H24T H 0.975476 0.915999 0.358334 0.162 Uiso 1 1 calc R . . . .
C2T C 0.8099(5) 0.091(2) 0.5309(4) 0.148(4) Uani 1 1 d D U . . .
C5 C 0.6786(5) 0.544(2) 0.4782(3) 0.124(3) Uani 1 1 d . . . . .
H5 H 0.696658 0.677999 0.497588 0.148 Uiso 1 1 calc R . . . .
C6 C 0.6823(4) 0.622(2) 0.4343(3) 0.125(3) Uani 1 1 d . . . . .
H6A H 0.655555 0.774892 0.428825 0.150 Uiso 1 1 calc R . . . .
H6B H 0.731039 0.660821 0.432137 0.150 Uiso 1 1 calc R . . . .
C2' C 0.5555(4) 0.771(2) 0.3379(3) 0.108(3) Uani 1 1 d . . . . .
H2'A H 0.601241 0.828250 0.351524 0.129 Uiso 1 1 calc R . . . .
H2'B H 0.519118 0.878411 0.345908 0.129 Uiso 1 1 calc R . . . .
C4 C 0.6050(4) 0.462(2) 0.4874(3) 0.122(3) Uani 1 1 d . . . . .
H4A H 0.609056 0.410115 0.516540 0.146 Uiso 1 1 calc R . . . .
H4B H 0.573528 0.604334 0.483757 0.146 Uiso 1 1 calc R . . . .
C27T C 0.8275(4) 1.136(2) 0.3761(3) 0.120(3) Uani 1 1 d D . . . .
H27T H 0.807310 1.266121 0.389158 0.144 Uiso 1 1 calc R . . . .
C1T C 0.7537(6) 0.283(3) 0.5274(4) 0.170(4) Uani 1 1 d . U . . .
H1TA H 0.716147 0.227067 0.542220 0.204 Uiso 1 1 calc R . . . .
H1TB H 0.772859 0.435533 0.540716 0.204 Uiso 1 1 calc R . . . .
C26T C 0.9472(5) 1.285(2) 0.4100(3) 0.154(4) Uani 1 1 d . . . . .
H26A H 0.983163 1.191207 0.427069 0.231 Uiso 1 1 calc GR . . . .
H26B H 0.920084 1.375336 0.427772 0.231 Uiso 1 1 calc GR . . . .
H26C H 0.968594 1.400042 0.392880 0.231 Uiso 1 1 calc GR . . . .
C12T C 0.3844(4) 0.853(2) 0.2185(3) 0.160(4) Uani 1 1 d D U . . .
C7T C 0.8382(6) 0.030(3) 0.4952(4) 0.176(5) Uani 1 1 d D U . . .
H7T H 0.824070 0.107688 0.469446 0.211 Uiso 1 1 calc R . . . .
C3T C 0.8291(6) -0.022(3) 0.5673(4) 0.182(6) Uani 1 1 d D U . . .
H3T H 0.807922 0.023874 0.590314 0.219 Uiso 1 1 calc R . . . .
C17T C 0.2806(10) 0.959(5) 0.1670(5) 0.270(10) Uani 1 1 d D U . . .
H17T H 0.260381 1.048866 0.143604 0.324 Uiso 1 1 calc R . . . .
C6T C 0.8900(7) -0.159(3) 0.5002(4) 0.201(6) Uani 1 1 d D U . . .
H6T H 0.909844 -0.210838 0.477073 0.242 Uiso 1 1 calc R . . . .
C13T C 0.3415(6) 0.684(4) 0.2360(6) 0.350(15) Uani 1 1 d D U . . .
H13T H 0.361849 0.577205 0.257106 0.420 Uiso 1 1 calc R . . . .
C18T C 0.3537(7) 0.985(4) 0.1842(4) 0.277(10) Uani 1 1 d D U . . .
H18T H 0.381254 1.095835 0.171549 0.333 Uiso 1 1 calc R . . . .
C4T C 0.8794(7) -0.205(3) 0.5721(5) 0.201(6) Uani 1 1 d D U . . .
H4T H 0.891430 -0.285861 0.597715 0.241 Uiso 1 1 calc R . . . .
C15T C 0.2417(6) 0.793(5) 0.1872(7) 0.276(10) Uani 1 1 d D U . . .
C5T C 0.9113(8) -0.265(3) 0.5384(5) 0.196(6) Uani 1 1 d D U . . .
H5T H 0.947965 -0.380092 0.541453 0.235 Uiso 1 1 calc R . . . .
C11T C 0.4561(5) 0.867(2) 0.2357(4) 0.141(4) Uani 1 1 d . U . . .
O11T O 0.4975(4) 0.952(3) 0.2182(3) 0.288(9) Uani 1 1 d . . . . .
C14T C 0.2680(7) 0.672(5) 0.2225(7) 0.396(18) Uani 1 1 d D U . . .
H14T H 0.238807 0.581922 0.237570 0.475 Uiso 1 1 calc R . . . .
C16T C 0.1603(8) 0.807(8) 0.1722(7) 0.412(18) Uani 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5' C21T 1.357(8) . ?
O5' C5' 1.444(8) . ?
O21T C21T 1.180(9) . ?
O1' C1' 1.421(9) . ?
O1' C4' 1.470(10) . ?
O5 C5 1.450(11) . ?
O5 C1T 1.422(11) . ?
O3' C3' 1.485(8) . ?
O3' C11T 1.270(11) . ?
C21T C22T 1.465(11) . ?
N1 C1' 1.495(10) . ?
N1 C7 1.515(8) . ?
N1 C2 1.330(10) . ?
C1' H1' 0.9800 . ?
C1' C2' 1.469(13) . ?
O2 C2 1.250(8) . ?
C4' H4' 0.9800 . ?
C4' C5' 1.481(10) . ?
C4' C3' 1.512(12) . ?
C22T C28T 1.413(9) . ?
C22T C23T 1.403(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C2 1.453(11) . ?
C3 C4 1.530(13) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C6 1.477(12) . ?
C5' H5'A 0.9700 . ?
C5' H5'B 0.9700 . ?
C25T C24T 1.427(13) . ?
C25T C27T 1.382(9) . ?
C25T C26T 1.491(13) . ?
C3' H3' 0.9800 . ?
C3' C2' 1.523(10) . ?
C28T H28T 0.9300 . ?
C28T C27T 1.346(11) . ?
C23T H23T 0.9300 . ?
C23T C24T 1.370(9) . ?
C24T H24T 0.9300 . ?
C2T C1T 1.485(16) . ?
C2T C7T 1.382(10) . ?
C2T C3T 1.323(14) . ?
C5 H5 0.9800 . ?
C5 C6 1.487(12) . ?
C5 C4 1.551(12) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C2' H2'A 0.9700 . ?
C2' H2'B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C27T H27T 0.9300 . ?
C1T H1TA 0.9700 . ?
C1T H1TB 0.9700 . ?
C26T H26A 0.9600 . ?
C26T H26B 0.9600 . ?
C26T H26C 0.9600 . ?
C12T C13T 1.402(17) . ?
C12T C18T 1.367(10) . ?
C12T C11T 1.407(12) . ?
C7T H7T 0.9300 . ?
C7T C6T 1.413(16) . ?
C3T H3T 0.9300 . ?
C3T C4T 1.372(11) . ?
C17T H17T 0.9300 . ?
C17T C18T 1.44(2) . ?
C17T C15T 1.388(12) . ?
C6T H6T 0.9300 . ?
C6T C5T 1.360(10) . ?
C13T H13T 0.9300 . ?
C13T C14T 1.414(11) . ?
C18T H18T 0.9300 . ?
C4T H4T 0.9300 . ?
C4T C5T 1.362(19) . ?
C15T C14T 1.34(2) . ?
C15T C16T 1.567(16) . ?
C5T H5T 0.9300 . ?
C11T O11T 1.137(11) . ?
C14T H14T 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
C21T O5' C5' 114.1(6) . . ?
C1' O1' C4' 109.6(7) . . ?
C1T O5 C5 114.9(9) . . ?
C11T O3' C3' 122.4(7) . . ?
O5' C21T C22T 112.9(8) . . ?
O21T C21T O5' 123.0(8) . . ?
O21T C21T C22T 124.0(7) . . ?
C1' N1 C7 117.9(6) . . ?
C2 N1 C1' 121.5(7) . . ?
C2 N1 C7 120.4(7) . . ?
O1' C1' N1 105.3(7) . . ?
O1' C1' H1' 109.8 . . ?
O1' C1' C2' 107.3(7) . . ?
N1 C1' H1' 109.8 . . ?
C2' C1' N1 114.7(9) . . ?
C2' C1' H1' 109.8 . . ?
O1' C4' H4' 109.3 . . ?
O1' C4' C5' 108.3(7) . . ?
O1' C4' C3' 103.7(7) . . ?
C5' C4' H4' 109.3 . . ?
C5' C4' C3' 116.8(8) . . ?
C3' C4' H4' 109.3 . . ?
C28T C22T C21T 124.2(7) . . ?
C23T C22T C21T 118.6(8) . . ?
C23T C22T C28T 117.2(8) . . ?
H3A C3 H3B 107.5 . . ?
C2 C3 H3A 108.5 . . ?
C2 C3 H3B 108.5 . . ?
C2 C3 C4 115.0(9) . . ?
C4 C3 H3A 108.5 . . ?
C4 C3 H3B 108.5 . . ?
N1 C7 H7A 108.7 . . ?
N1 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C6 C7 N1 114.3(6) . . ?
C6 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
N1 C2 C3 120.9(7) . . ?
O2 C2 N1 118.4(9) . . ?
O2 C2 C3 120.7(8) . . ?
O5' C5' C4' 109.6(6) . . ?
O5' C5' H5'A 109.8 . . ?
O5' C5' H5'B 109.8 . . ?
C4' C5' H5'A 109.8 . . ?
C4' C5' H5'B 109.8 . . ?
H5'A C5' H5'B 108.2 . . ?
C24T C25T C26T 122.1(8) . . ?
C27T C25T C24T 115.0(9) . . ?
C27T C25T C26T 122.7(11) . . ?
O3' C3' C4' 109.9(8) . . ?
O3' C3' H3' 111.4 . . ?
O3' C3' C2' 106.3(6) . . ?
C4' C3' H3' 111.4 . . ?
C4' C3' C2' 106.3(8) . . ?
C2' C3' H3' 111.4 . . ?
C22T C28T H28T 119.0 . . ?
C27T C28T C22T 122.0(8) . . ?
C27T C28T H28T 119.0 . . ?
C22T C23T H23T 120.3 . . ?
C24T C23T C22T 119.3(8) . . ?
C24T C23T H23T 120.3 . . ?
C25T C24T H24T 118.3 . . ?
C23T C24T C25T 123.4(8) . . ?
C23T C24T H24T 118.3 . . ?
C7T C2T C1T 118.5(11) . . ?
C3T C2T C1T 119.3(12) . . ?
C3T C2T C7T 122.2(14) . . ?
O5 C5 H5 109.4 . . ?
O5 C5 C6 104.0(8) . . ?
O5 C5 C4 108.5(8) . . ?
C6 C5 H5 109.4 . . ?
C6 C5 C4 115.8(8) . . ?
C4 C5 H5 109.4 . . ?
C7 C6 C5 116.5(9) . . ?
C7 C6 H6A 108.2 . . ?
C7 C6 H6B 108.2 . . ?
C5 C6 H6A 108.2 . . ?
C5 C6 H6B 108.2 . . ?
H6A C6 H6B 107.3 . . ?
C1' C2' C3' 101.0(8) . . ?
C1' C2' H2'A 111.6 . . ?
C1' C2' H2'B 111.6 . . ?
C3' C2' H2'A 111.6 . . ?
C3' C2' H2'B 111.6 . . ?
H2'A C2' H2'B 109.4 . . ?
C3 C4 C5 113.8(7) . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C5 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C25T C27T H27T 118.7 . . ?
C28T C27T C25T 122.7(10) . . ?
C28T C27T H27T 118.7 . . ?
O5 C1T C2T 111.5(10) . . ?
O5 C1T H1TA 109.3 . . ?
O5 C1T H1TB 109.3 . . ?
C2T C1T H1TA 109.3 . . ?
C2T C1T H1TB 109.3 . . ?
H1TA C1T H1TB 108.0 . . ?
C25T C26T H26A 109.5 . . ?
C25T C26T H26B 109.5 . . ?
C25T C26T H26C 109.5 . . ?
H26A C26T H26B 109.5 . . ?
H26A C26T H26C 109.5 . . ?
H26B C26T H26C 109.5 . . ?
C13T C12T C11T 118.4(11) . . ?
C18T C12T C13T 116.9(10) . . ?
C18T C12T C11T 124.6(12) . . ?
C2T C7T H7T 122.2 . . ?
C2T C7T C6T 115.7(13) . . ?
C6T C7T H7T 122.2 . . ?
C2T C3T H3T 119.0 . . ?
C2T C3T C4T 121.9(15) . . ?
C4T C3T H3T 119.0 . . ?
C18T C17T H17T 121.7 . . ?
C15T C17T H17T 121.7 . . ?
C15T C17T C18T 116.6(12) . . ?
C7T C6T H6T 119.4 . . ?
C5T C6T C7T 121.3(14) . . ?
C5T C6T H6T 119.4 . . ?
C12T C13T H13T 119.1 . . ?
C12T C13T C14T 121.8(14) . . ?
C14T C13T H13T 119.1 . . ?
C12T C18T C17T 122.5(14) . . ?
C12T C18T H18T 118.8 . . ?
C17T C18T H18T 118.8 . . ?
C3T C4T H4T 120.8 . . ?
C5T C4T C3T 118.4(16) . . ?
C5T C4T H4T 120.8 . . ?
C17T C15T C16T 114(2) . . ?
C14T C15T C17T 123.3(11) . . ?
C14T C15T C16T 121.2(19) . . ?
C6T C5T C4T 120.4(16) . . ?
C6T C5T H5T 119.8 . . ?
C4T C5T H5T 119.8 . . ?
O3' C11T C12T 119.5(10) . . ?
O11T C11T O3' 117.8(11) . . ?
O11T C11T C12T 122.8(13) . . ?
C13T C14T H14T 121.0 . . ?
C15T C14T C13T 118.0(15) . . ?
C15T C14T H14T 121.0 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.283 0.500 9.6 0.7 ?
2 0.122 0.311 0.087 73.7 15.8 ?
3 -0.122 0.311 0.913 73.7 15.9 ?
4 0.378 0.811 0.413 73.7 15.9 ?
5 0.500 0.783 0.000 9.6 0.7 ?
6 0.622 0.811 0.587 73.7 15.8 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_hari_0m
_database_code_depnum_ccdc_archive 'CCDC 2207174'
loop_
_audit_author_name
_audit_author_address
'Geoffrey Jameson'
;School of Natural Sciences, Massey University
New Zealand
;
_audit_update_record             
;
2022-09-14 deposited with the CCDC.	2023-05-23 downloaded from the CCDC.
;
_audit_creation_date             2022-09-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
'1-[2-deoxy-3,5-bis-O-(4-methylbenzoyl)-β-D-erythro-pentofuranosyl]-(S)-5-benzyloxyazepan-2-one '
_chemical_formula_moiety         'C34 H37 N O7'
_chemical_formula_sum            'C34 H37 N O7'
_chemical_formula_weight         571.64
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
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                   33.3058(16)
_cell_length_b                   5.5217(3)
_cell_length_c                   17.9538(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.418(2)
_cell_angle_gamma                90
_cell_volume                     3167.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9873
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      58.810
_cell_measurement_theta_min      2.566
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.876
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.6311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1035 before and 0.0444 after correction.
The Ratio of minimum to maximum transmission is 0.8397.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18253
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        59.414
_diffrn_reflns_theta_max         59.414
_diffrn_reflns_theta_min         2.566
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Micro-focus sealed source'
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_full    0.945
_reflns_Friedel_fraction_max     0.945
_reflns_number_gt                4102
_reflns_number_total             4471
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_atom_sites_solution_primary     .
_refine_diff_density_max         0.765
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 1573 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     381
_refine_ls_number_reflns         4471
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0536
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0935P)²+2.5551P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1481
_refine_special_details          
;
Residual positive electron density (0.76 e A⁻³)was concentrated near the phenyl ring undergoing substantial torsional motion about C5-O5 and C1T-C2T bonds, leading to Alert B for Hirshfeld Tests. 
Absolute structure was determined by Flack x (-0.02(9) and Hooft  y (0.04(8) parameters. The expected beta-D-2-deoxyribose was observed, establishing the S-diasteromer at nucleobase atom C5.
The data:parameter ratio is 6.70, partly due to chiral space group and partly due to data cutoff in processing at sine(theta_max)/wavelength of 0.5584 A⁻¹.
Four reflections were jected for poor agreement of Fcalc and Fobs.   
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3'(H3'), C4'(H4'), C1'(H1'), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2'(H2'A,H2'B), C7(H7A,H7B), C4(H4A,H4B), C6(H6A,H6B), C5'(H5'A,H5'B), C3(H3A,
 H3B), C1T(H1TA,H1TB)
2.c Aromatic/amide H refined with riding coordinates:
 C18T(H18T), C17T(H17T), C13T(H13T), C28T(H28T), C14T(H14T), C23T(H23T),
 C24T(H24T), C27T(H27T), C7T(H7T), C4T(H4T), C5T(H5T), C3T(H3T), C6T(H6T)
2.d Idealised Me refined as rotating group:
 C16T(H16A,H16B,H16C), C26T(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_secondary   ?
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
O3' O 0.74601(8) 0.0105(5) 0.22987(15) 0.0296(7) Uani 1 1 d . . . . .
O5' O 0.68916(8) -0.0348(6) 0.41864(15) 0.0334(7) Uani 1 1 d . . . . .
O1' O 0.66652(8) -0.2045(5) 0.26164(16) 0.0343(7) Uani 1 1 d . . . . .
O11T O 0.77523(10) 0.3801(6) 0.24439(17) 0.0404(8) Uani 1 1 d . . . . .
O5 O 0.51760(10) 0.6260(6) 0.19243(19) 0.0424(8) Uani 1 1 d . . . . .
O2 O 0.60686(10) -0.0504(7) 0.06171(17) 0.0470(9) Uani 1 1 d . . . . .
O21T O 0.72042(10) -0.1636(7) 0.53978(17) 0.0467(9) Uani 1 1 d . . . . .
N1 N 0.61280(10) 0.0443(7) 0.18746(19) 0.0318(8) Uani 1 1 d . . . . .
C12T C 0.78664(12) 0.1124(8) 0.1472(2) 0.0284(9) Uani 1 1 d . . . . .
C11T C 0.76950(12) 0.1851(8) 0.2117(2) 0.0302(10) Uani 1 1 d . . . . .
C3' C 0.72500(12) 0.0621(8) 0.2890(2) 0.0282(9) Uani 1 1 d . . . . .
H3' H 0.743602 0.145117 0.335586 0.034 Uiso 1 1 calc R . . . .
C2 C 0.59041(13) 0.0174(9) 0.1110(2) 0.0353(10) Uani 1 1 d . . . . .
C2' C 0.68517(12) 0.2006(8) 0.2531(2) 0.0281(9) Uani 1 1 d . . . . .
H2'A H 0.689462 0.328740 0.217501 0.034 Uiso 1 1 calc R . . . .
H2'B H 0.673706 0.273677 0.293084 0.034 Uiso 1 1 calc R . . . .
C4' C 0.70956(12) -0.1843(8) 0.3083(2) 0.0307(9) Uani 1 1 d . . . . .
H4' H 0.726288 -0.313559 0.291901 0.037 Uiso 1 1 calc R . . . .
C18T C 0.77478(13) -0.1023(8) 0.1065(2) 0.0334(10) Uani 1 1 d . . . . .
H18T H 0.756973 -0.213242 0.122286 0.040 Uiso 1 1 calc R . . . .
C1' C 0.65720(12) -0.0013(8) 0.2092(2) 0.0290(9) Uani 1 1 d . . . . .
H1' H 0.665738 -0.041523 0.161549 0.035 Uiso 1 1 calc R . . . .
C17T C 0.78897(14) -0.1539(9) 0.0429(2) 0.0368(10) Uani 1 1 d . . . . .
H17T H 0.780692 -0.300583 0.015123 0.044 Uiso 1 1 calc R . . . .
C15T C 0.81519(13) 0.0056(9) 0.0189(2) 0.0359(10) Uani 1 1 d . . . . .
C21T C 0.69682(13) -0.0279(9) 0.4964(2) 0.0345(11) Uani 1 1 d . . . . .
C13T C 0.81368(14) 0.2711(8) 0.1246(2) 0.0363(10) Uani 1 1 d . . . . .
H13T H 0.822284 0.417149 0.152535 0.044 Uiso 1 1 calc R . . . .
C5 C 0.53401(14) 0.3875(9) 0.1888(3) 0.0377(11) Uani 1 1 d . . . . .
H5 H 0.514200 0.268173 0.201092 0.045 Uiso 1 1 calc R . . . .
C7 C 0.59289(13) 0.0982(9) 0.2491(2) 0.0358(11) Uani 1 1 d . . . . .
H7A H 0.613506 0.068758 0.300075 0.043 Uiso 1 1 calc R . . . .
H7B H 0.569344 -0.015829 0.244271 0.043 Uiso 1 1 calc R . . . .
C4 C 0.53512(14) 0.3439(10) 0.1061(3) 0.0416(11) Uani 1 1 d . . . . .
H4A H 0.556548 0.451116 0.094938 0.050 Uiso 1 1 calc R . . . .
H4B H 0.507667 0.389510 0.070293 0.050 Uiso 1 1 calc R . . . .
C6 C 0.57642(13) 0.3557(9) 0.2479(2) 0.0372(11) Uani 1 1 d . . . . .
H6A H 0.574075 0.397299 0.300148 0.045 Uiso 1 1 calc R . . . .
H6B H 0.596659 0.468988 0.235526 0.045 Uiso 1 1 calc R . . . .
C5' C 0.71248(13) -0.2212(9) 0.3925(2) 0.0343(10) Uani 1 1 d . . . . .
H5'A H 0.701095 -0.382295 0.399798 0.041 Uiso 1 1 calc R . . . .
H5'B H 0.742168 -0.215575 0.423789 0.041 Uiso 1 1 calc R . . . .
C28T C 0.64715(15) 0.3297(10) 0.4713(3) 0.0454(12) Uani 1 1 d . . . . .
H28T H 0.643739 0.317292 0.417104 0.054 Uiso 1 1 calc R . . . .
C22T C 0.67287(13) 0.1681(10) 0.5217(2) 0.0399(11) Uani 1 1 d . . . . .
C3 C 0.54487(14) 0.0814(9) 0.0895(3) 0.0400(11) Uani 1 1 d . . . . .
H3A H 0.530770 -0.027473 0.117980 0.048 Uiso 1 1 calc R . . . .
H3B H 0.532643 0.049756 0.033331 0.048 Uiso 1 1 calc R . . . .
C14T C 0.82783(15) 0.2145(9) 0.0616(3) 0.0403(11) Uani 1 1 d . . . . .
H14T H 0.846679 0.321477 0.047103 0.048 Uiso 1 1 calc R . . . .
C16T C 0.82914(17) -0.0497(10) -0.0525(3) 0.0503(13) Uani 1 1 d . . . . .
H16A H 0.835478 -0.222758 -0.053623 0.076 Uiso 1 1 calc GR . . . .
H16B H 0.854246 0.044917 -0.051045 0.076 Uiso 1 1 calc GR . . . .
H16C H 0.806721 -0.007090 -0.099150 0.076 Uiso 1 1 calc GR . . . .
C23T C 0.67806(15) 0.1905(12) 0.6020(3) 0.0528(14) Uani 1 1 d . . . . .
H23T H 0.696103 0.082107 0.637129 0.063 Uiso 1 1 calc R . . . .
C24T C 0.65754(18) 0.3654(13) 0.6298(3) 0.0614(17) Uani 1 1 d . . . . .
H24T H 0.661101 0.376409 0.684077 0.074 Uiso 1 1 calc R . . . .
C25T C 0.6316(2) 0.5275(13) 0.5803(4) 0.0667(19) Uani 1 1 d . . . . .
C27T C 0.62637(18) 0.5092(12) 0.4992(3) 0.0605(15) Uani 1 1 d . . . . .
H27T H 0.608704 0.619814 0.464349 0.073 Uiso 1 1 calc R . . . .
C7T C 0.4475(2) 0.9038(14) 0.1594(5) 0.078(2) Uani 1 1 d . . . . .
H7T H 0.452568 0.799745 0.120870 0.093 Uiso 1 1 calc R . . . .
C4T C 0.4275(2) 1.1500(15) 0.2707(4) 0.079(2) Uani 1 1 d . . . . .
H4T H 0.419902 1.215783 0.313720 0.094 Uiso 1 1 calc R . . . .
C5T C 0.4083(2) 1.2355(17) 0.1995(6) 0.096(3) Uani 1 1 d . . . . .
H5T H 0.389870 1.370210 0.191392 0.116 Uiso 1 1 calc R . . . .
C2T C 0.4666(2) 0.8644(14) 0.2316(6) 0.085(2) Uani 1 1 d . . . . .
C26T C 0.6087(3) 0.7219(15) 0.6110(5) 0.093(2) Uani 1 1 d . . . . .
H26A H 0.583190 0.653976 0.619401 0.139 Uiso 1 1 calc GR . . . .
H26B H 0.601373 0.854540 0.573317 0.139 Uiso 1 1 calc GR . . . .
H26C H 0.626827 0.783699 0.660277 0.139 Uiso 1 1 calc GR . . . .
C3T C 0.4559(3) 0.9821(19) 0.2838(6) 0.110(3) Uani 1 1 d . . . . .
H3T H 0.469837 0.944282 0.336385 0.132 Uiso 1 1 calc R . . . .
C6T C 0.4178(2) 1.107(2) 0.1353(4) 0.119(4) Uani 1 1 d . . . . .
H6T H 0.405921 1.151247 0.082534 0.143 Uiso 1 1 calc R . . . .
C1T C 0.5007(3) 0.6621(17) 0.2533(5) 0.102(3) Uani 1 1 d . . . . .
H1TA H 0.523048 0.710534 0.300261 0.122 Uiso 1 1 calc R . . . .
H1TB H 0.488065 0.509599 0.264947 0.122 Uiso 1 1 calc R . . . .


_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
O3' C11T 1.338(5) . ?
O3' C3' 1.456(5) . ?
O5' C21T 1.347(5) . ?
O5' C5' 1.445(5) . ?
O1' C4' 1.446(5) . ?
O1' C1' 1.441(5) . ?
O11T C11T 1.216(5) . ?
O5 C5 1.434(6) . ?
O5 C1T 1.378(9) . ?
O2 C2 1.224(5) . ?
O21T C21T 1.200(5) . ?
N1 C2 1.372(5) . ?
N1 C1' 1.441(5) . ?
N1 C7 1.472(5) . ?
C12T C11T 1.484(6) . ?
C12T C18T 1.390(6) . ?
C12T C13T 1.396(6) . ?
C3' H3' 1.0000 . ?
C3' C2' 1.509(6) . ?
C3' C4' 1.528(6) . ?
C2 C3 1.498(6) . ?
C2' H2'A 0.9900 . ?
C2' H2'B 0.9900 . ?
C2' C1' 1.522(6) . ?
C4' H4' 1.0000 . ?
C4' C5' 1.501(6) . ?
C18T H18T 0.9500 . ?
C18T C17T 1.383(6) . ?
C1' H1' 1.0000 . ?
C17T H17T 0.9500 . ?
C17T C15T 1.391(7) . ?
C15T C14T 1.382(7) . ?
C15T C16T 1.514(6) . ?
C21T C22T 1.489(7) . ?
C13T H13T 0.9500 . ?
C13T C14T 1.380(6) . ?
C5 H5 1.0000 . ?
C5 C4 1.516(6) . ?
C5 C6 1.518(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C6 1.522(7) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.533(7) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C5' H5'A 0.9900 . ?
C5' H5'B 0.9900 . ?
C28T H28T 0.9500 . ?
C28T C22T 1.382(7) . ?
C28T C27T 1.381(8) . ?
C22T C23T 1.409(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C14T H14T 0.9500 . ?
C16T H16A 0.9800 . ?
C16T H16B 0.9800 . ?
C16T H16C 0.9800 . ?
C23T H23T 0.9500 . ?
C23T C24T 1.356(9) . ?
C24T H24T 0.9500 . ?
C24T C25T 1.380(10) . ?
C25T C27T 1.420(9) . ?
C25T C26T 1.507(9) . ?
C27T H27T 0.9500 . ?
C7T H7T 0.9500 . ?
C7T C2T 1.291(11) . ?
C7T C6T 1.478(14) . ?
C4T H4T 0.9500 . ?
C4T C5T 1.343(10) . ?
C4T C3T 1.298(11) . ?
C5T H5T 0.9500 . ?
C5T C6T 1.460(13) . ?
C2T C3T 1.271(12) . ?
C2T C1T 1.562(11) . ?
C26T H26A 0.9800 . ?
C26T H26B 0.9800 . ?
C26T H26C 0.9800 . ?
C3T H3T 0.9500 . ?
C6T H6T 0.9500 . ?
C1T H1TA 0.9900 . ?
C1T H1TB 0.9900 . ?

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
C11T O3' C3' 118.2(3) . . ?
C21T O5' C5' 113.2(3) . . ?
C1' O1' C4' 108.3(3) . . ?
C1T O5 C5 114.5(5) . . ?
C2 N1 C1' 118.6(3) . . ?
C2 N1 C7 122.7(3) . . ?
C1' N1 C7 118.5(3) . . ?
C18T C12T C11T 121.7(4) . . ?
C18T C12T C13T 119.6(4) . . ?
C13T C12T C11T 118.6(4) . . ?
O3' C11T C12T 112.1(4) . . ?
O11T C11T O3' 122.9(4) . . ?
O11T C11T C12T 125.0(4) . . ?
O3' C3' H3' 112.8 . . ?
O3' C3' C2' 109.4(3) . . ?
O3' C3' C4' 104.7(3) . . ?
C2' C3' H3' 112.8 . . ?
C2' C3' C4' 103.7(3) . . ?
C4' C3' H3' 112.8 . . ?
O2 C2 N1 121.9(4) . . ?
O2 C2 C3 120.8(4) . . ?
N1 C2 C3 117.2(4) . . ?
C3' C2' H2'A 111.6 . . ?
C3' C2' H2'B 111.6 . . ?
C3' C2' C1' 100.7(3) . . ?
H2'A C2' H2'B 109.4 . . ?
C1' C2' H2'A 111.6 . . ?
C1' C2' H2'B 111.6 . . ?
O1' C4' C3' 106.2(3) . . ?
O1' C4' H4' 108.5 . . ?
O1' C4' C5' 110.2(3) . . ?
C3' C4' H4' 108.5 . . ?
C5' C4' C3' 114.8(4) . . ?
C5' C4' H4' 108.5 . . ?
C12T C18T H18T 120.1 . . ?
C17T C18T C12T 119.8(4) . . ?
C17T C18T H18T 120.1 . . ?
O1' C1' C2' 104.2(3) . . ?
O1' C1' H1' 109.0 . . ?
N1 C1' O1' 109.1(3) . . ?
N1 C1' C2' 116.3(4) . . ?
N1 C1' H1' 109.0 . . ?
C2' C1' H1' 109.0 . . ?
C18T C17T H17T 119.5 . . ?
C18T C17T C15T 121.0(4) . . ?
C15T C17T H17T 119.5 . . ?
C17T C15T C16T 120.2(4) . . ?
C14T C15T C17T 118.5(4) . . ?
C14T C15T C16T 121.3(4) . . ?
O5' C21T C22T 112.1(4) . . ?
O21T C21T O5' 123.5(4) . . ?
O21T C21T C22T 124.4(4) . . ?
C12T C13T H13T 120.2 . . ?
C14T C13T C12T 119.6(4) . . ?
C14T C13T H13T 120.2 . . ?
O5 C5 H5 108.2 . . ?
O5 C5 C4 107.8(4) . . ?
O5 C5 C6 111.5(4) . . ?
C4 C5 H5 108.2 . . ?
C4 C5 C6 113.0(4) . . ?
C6 C5 H5 108.2 . . ?
N1 C7 H7A 108.6 . . ?
N1 C7 H7B 108.6 . . ?
N1 C7 C6 114.5(4) . . ?
H7A C7 H7B 107.6 . . ?
C6 C7 H7A 108.6 . . ?
C6 C7 H7B 108.6 . . ?
C5 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C5 C4 C3 113.9(4) . . ?
H4A C4 H4B 107.7 . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C5 C6 C7 112.2(4) . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
O5' C5' C4' 110.0(3) . . ?
O5' C5' H5'A 109.7 . . ?
O5' C5' H5'B 109.7 . . ?
C4' C5' H5'A 109.7 . . ?
C4' C5' H5'B 109.7 . . ?
H5'A C5' H5'B 108.2 . . ?
C22T C28T H28T 119.7 . . ?
C27T C28T H28T 119.7 . . ?
C27T C28T C22T 120.5(5) . . ?
C28T C22T C21T 123.8(4) . . ?
C28T C22T C23T 119.1(5) . . ?
C23T C22T C21T 117.0(5) . . ?
C2 C3 C4 115.3(4) . . ?
C2 C3 H3A 108.4 . . ?
C2 C3 H3B 108.4 . . ?
C4 C3 H3A 108.4 . . ?
C4 C3 H3B 108.4 . . ?
H3A C3 H3B 107.5 . . ?
C15T C14T H14T 119.3 . . ?
C13T C14T C15T 121.5(4) . . ?
C13T C14T H14T 119.3 . . ?
C15T C16T H16A 109.5 . . ?
C15T C16T H16B 109.5 . . ?
C15T C16T H16C 109.5 . . ?
H16A C16T H16B 109.5 . . ?
H16A C16T H16C 109.5 . . ?
H16B C16T H16C 109.5 . . ?
C22T C23T H23T 119.7 . . ?
C24T C23T C22T 120.7(6) . . ?
C24T C23T H23T 119.7 . . ?
C23T C24T H24T 119.5 . . ?
C23T C24T C25T 120.9(5) . . ?
C25T C24T H24T 119.5 . . ?
C24T C25T C27T 119.1(6) . . ?
C24T C25T C26T 121.0(6) . . ?
C27T C25T C26T 119.8(7) . . ?
C28T C27T C25T 119.6(6) . . ?
C28T C27T H27T 120.2 . . ?
C25T C27T H27T 120.2 . . ?
C2T C7T H7T 119.3 . . ?
C2T C7T C6T 121.4(7) . . ?
C6T C7T H7T 119.3 . . ?
C5T C4T H4T 118.4 . . ?
C3T C4T H4T 118.4 . . ?
C3T C4T C5T 123.3(8) . . ?
C4T C5T H5T 122.3 . . ?
C4T C5T C6T 115.5(7) . . ?
C6T C5T H5T 122.3 . . ?
C7T C2T C1T 119.3(8) . . ?
C3T C2T C7T 119.5(8) . . ?
C3T C2T C1T 121.1(9) . . ?
C25T C26T H26A 109.5 . . ?
C25T C26T H26B 109.5 . . ?
C25T C26T H26C 109.5 . . ?
H26A C26T H26B 109.5 . . ?
H26A C26T H26C 109.5 . . ?
H26B C26T H26C 109.5 . . ?
C4T C3T H3T 117.5 . . ?
C2T C3T C4T 125.0(10) . . ?
C2T C3T H3T 117.5 . . ?
C7T C6T H6T 122.8 . . ?
C5T C6T C7T 114.5(7) . . ?
C5T C6T H6T 122.8 . . ?
O5 C1T C2T 109.6(7) . . ?
O5 C1T H1TA 109.7 . . ?
O5 C1T H1TB 109.7 . . ?
C2T C1T H1TA 109.7 . . ?
C2T C1T H1TB 109.7 . . ?
H1TA C1T H1TB 108.2 . . ?

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
O3' C3' C2' C1' 75.5(4) . . . . ?
O3' C3' C4' O1' -95.8(3) . . . . ?
O3' C3' C4' C5' 142.2(3) . . . . ?
O5' C21T C22T C28T -2.5(6) . . . . ?
O5' C21T C22T C23T 179.2(4) . . . . ?
O1' C4' C5' O5' -62.3(5) . . . . ?
O5 C5 C4 C3 -170.1(4) . . . . ?
O5 C5 C6 C7 175.8(3) . . . . ?
O2 C2 C3 C4 -118.7(5) . . . . ?
O21T C21T C22T C28T 177.1(5) . . . . ?
O21T C21T C22T C23T -1.2(7) . . . . ?
N1 C2 C3 C4 59.6(6) . . . . ?
N1 C7 C6 C5 81.0(4) . . . . ?
C12T C18T C17T C15T 0.2(6) . . . . ?
C12T C13T C14T C15T 1.3(7) . . . . ?
C11T O3' C3' C2' 81.5(4) . . . . ?
C11T O3' C3' C4' -167.9(3) . . . . ?
C11T C12T C18T C17T 174.9(4) . . . . ?
C11T C12T C13T C14T -175.8(4) . . . . ?
C3' O3' C11T O11T 2.9(6) . . . . ?
C3' O3' C11T C12T -176.3(3) . . . . ?
C3' C2' C1' O1' 40.8(4) . . . . ?
C3' C2' C1' N1 161.0(3) . . . . ?
C3' C4' C5' O5' 57.6(4) . . . . ?
C2 N1 C1' O1' -116.3(4) . . . . ?
C2 N1 C1' C2' 126.2(4) . . . . ?
C2 N1 C7 C6 -72.6(5) . . . . ?
C2' C3' C4' O1' 18.9(4) . . . . ?
C2' C3' C4' C5' -103.1(4) . . . . ?
C4' O1' C1' N1 -155.2(3) . . . . ?
C4' O1' C1' C2' -30.3(4) . . . . ?
C4' C3' C2' C1' -35.8(4) . . . . ?
C18T C12T C11T O3' 6.9(5) . . . . ?
C18T C12T C11T O11T -172.2(4) . . . . ?
C18T C12T C13T C14T 0.9(6) . . . . ?
C18T C17T C15T C14T 1.9(6) . . . . ?
C18T C17T C15T C16T -177.8(4) . . . . ?
C1' O1' C4' C3' 7.1(4) . . . . ?
C1' O1' C4' C5' 132.0(4) . . . . ?
C1' N1 C2 O2 2.1(7) . . . . ?
C1' N1 C2 C3 -176.2(4) . . . . ?
C1' N1 C7 C6 112.6(4) . . . . ?
C17T C15T C14T C13T -2.7(7) . . . . ?
C21T O5' C5' C4' -167.9(3) . . . . ?
C21T C22T C23T C24T 179.6(5) . . . . ?
C13T C12T C11T O3' -176.5(4) . . . . ?
C13T C12T C11T O11T 4.4(6) . . . . ?
C13T C12T C18T C17T -1.6(6) . . . . ?
C5 O5 C1T C2T -153.3(5) . . . . ?
C5 C4 C3 C2 -84.0(5) . . . . ?
C7 N1 C2 O2 -172.8(4) . . . . ?
C7 N1 C2 C3 9.0(6) . . . . ?
C7 N1 C1' O1' 58.8(5) . . . . ?
C7 N1 C1' C2' -58.7(5) . . . . ?
C4 C5 C6 C7 -62.7(5) . . . . ?
C6 C5 C4 C3 66.3(5) . . . . ?
C5' O5' C21T O21T -0.5(6) . . . . ?
C5' O5' C21T C22T 179.1(3) . . . . ?
C28T C22T C23T C24T 1.2(7) . . . . ?
C22T C28T C27T C25T 0.1(8) . . . . ?
C22T C23T C24T C25T -0.9(8) . . . . ?
C16T C15T C14T C13T 177.0(4) . . . . ?
C23T C24T C25T C27T 0.1(8) . . . . ?
C23T C24T C25T C26T 180.0(5) . . . . ?
C24T C25T C27T C28T 0.3(8) . . . . ?
C27T C28T C22T C21T -179.1(5) . . . . ?
C27T C28T C22T C23T -0.8(7) . . . . ?
C7T C2T C3T C4T -2.5(14) . . . . ?
C7T C2T C1T O5 25.6(10) . . . . ?
C4T C5T C6T C7T -0.4(11) . . . . ?
C5T C4T C3T C2T -6.2(15) . . . . ?
C2T C7T C6T C5T -7.5(11) . . . . ?
C26T C25T C27T C28T -179.6(6) . . . . ?
C3T C4T C5T C6T 7.0(13) . . . . ?
C3T C2T C1T O5 -157.9(8) . . . . ?
C6T C7T C2T C3T 9.2(11) . . . . ?
C6T C7T C2T C1T -174.3(7) . . . . ?
C1T O5 C5 C4 157.9(5) . . . . ?
C1T O5 C5 C6 -77.6(6) . . . . ?
C1T C2T C3T C4T -178.9(8) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 -0.231 0.500 152.2 35.8 '2 methanol'
2 0.073 0.000 0.975 7.3 0.3 ?
3 0.500 -0.997 0.500 152.2 35.8 '2 methanol'
4 0.427 0.500 0.025 7.3 0.3 ?
5 0.573 0.500 0.975 7.3 0.3 ?
6 0.927 0.000 0.025 7.3 0.3 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
