# Electronic Supplementary Material (ESI) for ChemComm.
# 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_aa695_mo
_database_code_depnum_ccdc_archive 'CCDC 2174962'
loop_
_audit_author_name
_audit_author_address
'Christopher Pask'
;University of Leeds
United Kingdom
;
_audit_update_record             
;
2022-05-25 deposited with the CCDC.	2022-12-12 downloaded from the CCDC.
;
_audit_creation_date             2015-10-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H19 N O5'
_chemical_formula_sum            'C15 H19 N O5'
_chemical_formula_weight         293.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H19N1O5
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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.1141(4)
_cell_length_b                   7.4519(4)
_cell_length_c                   18.8419(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.346(4)
_cell_angle_gamma                90
_cell_volume                     1411.40(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7076
_cell_measurement_temperature    120.00(15)
_cell_measurement_theta_max      30.8300
_cell_measurement_theta_min      4.0110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19778
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.228
_diffrn_reflns_theta_min         2.942
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(15)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   81.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       12.9509   57.0000 -150.0000 93

#__ type_ start__ end____ width___ exp.time_
  2 omega  -72.00   98.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       12.9509    0.0000 -180.0000 170

#__ type_ start__ end____ width___ exp.time_
  3 omega  -12.00   81.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       12.9509   57.0000   90.0000 93

#__ type_ start__ end____ width___ exp.time_
  4 omega  -58.00  -33.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       12.9509  -37.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
  5 omega  -55.00   38.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       12.9509  -57.0000   60.0000 93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0572225000
_diffrn_orient_matrix_UB_12      -0.0459762000
_diffrn_orient_matrix_UB_13      0.0090531000
_diffrn_orient_matrix_UB_21      -0.0397173000
_diffrn_orient_matrix_UB_22      0.0760010000
_diffrn_orient_matrix_UB_23      -0.0103646000
_diffrn_orient_matrix_UB_31      -0.0112429000
_diffrn_orient_matrix_UB_32      -0.0341615000
_diffrn_orient_matrix_UB_33      -0.0352898000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3474
_reflns_number_total             4269
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         4269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0521
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0474P)²+0.8579P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1222
_refine_ls_wR_factor_ref         0.1309
_refine_special_details          ?
_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:
 C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_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
O1 O 0.76382(10) 0.52518(14) 0.22973(5) 0.0209(2) Uani 1 1 d . . . . .
N1 N 0.88051(11) 0.76246(15) 0.28360(6) 0.0158(2) Uani 1 1 d . . . . .
C1 C 0.80225(12) 0.61381(18) 0.28251(7) 0.0159(3) Uani 1 1 d . . . . .
O2 O 0.53447(12) 0.58936(18) 0.37044(9) 0.0436(4) Uani 1 1 d . . . . .
C2 C 0.76882(13) 0.58258(18) 0.35946(7) 0.0166(3) Uani 1 1 d . . . . .
H2 H 0.8346 0.5023 0.3849 0.020 Uiso 1 1 calc R . . . .
O3 O 0.62940(10) 0.33057(15) 0.34269(6) 0.0266(3) Uani 1 1 d . . . . .
C3 C 0.78252(13) 0.77283(18) 0.39118(7) 0.0164(3) Uani 1 1 d . . . . .
H3 H 0.7007 0.8390 0.3757 0.020 Uiso 1 1 calc R . . . .
O4 O 0.96156(11) 0.65028(15) 0.56198(5) 0.0226(2) Uani 1 1 d . . . . .
C4 C 0.80725(14) 0.7838(2) 0.47248(7) 0.0201(3) Uani 1 1 d . . . . .
H4A H 0.7970 0.9076 0.4869 0.024 Uiso 1 1 calc R . . . .
H4B H 0.7400 0.7133 0.4927 0.024 Uiso 1 1 calc R . . . .
O5 O 1.17358(10) 0.70329(15) 0.49348(5) 0.0212(2) Uani 1 1 d . . . . .
C5 C 0.94257(14) 0.71852(19) 0.50301(7) 0.0182(3) Uani 1 1 d . . . . .
C6 C 1.05286(13) 0.74887(18) 0.45839(7) 0.0172(3) Uani 1 1 d . . . . .
C7 C 1.03144(13) 0.81479(19) 0.39203(7) 0.0171(3) Uani 1 1 d . . . . .
H7 H 1.1051 0.8374 0.3679 0.021 Uiso 1 1 calc R . . . .
C8 C 0.89585(13) 0.85485(18) 0.35375(7) 0.0159(3) Uani 1 1 d . . . . .
C9 C 0.88081(15) 1.05577(19) 0.33361(7) 0.0196(3) Uani 1 1 d . . . . .
H9A H 0.8249 1.1170 0.3646 0.024 Uiso 1 1 calc R . . . .
H9B H 0.9669 1.1145 0.3373 0.024 Uiso 1 1 calc R . . . .
C10 C 0.81586(15) 1.0555(2) 0.25624(8) 0.0216(3) Uani 1 1 d . . . . .
H10A H 0.8372 1.1642 0.2316 0.026 Uiso 1 1 calc R . . . .
H10B H 0.7200 1.0442 0.2541 0.026 Uiso 1 1 calc R . . . .
C11 C 0.87717(14) 0.89038(19) 0.22420(7) 0.0188(3) Uani 1 1 d . . . . .
H11A H 0.8220 0.8470 0.1823 0.023 Uiso 1 1 calc R . . . .
H11B H 0.9658 0.9155 0.2117 0.023 Uiso 1 1 calc R . . . .
C12 C 0.63066(14) 0.5046(2) 0.35900(8) 0.0211(3) Uani 1 1 d . . . . .
C13 C 0.50058(15) 0.2417(2) 0.33279(9) 0.0292(3) Uani 1 1 d . . . . .
H13A H 0.5027 0.1472 0.2975 0.035 Uiso 1 1 calc R . . . .
H13B H 0.4330 0.3277 0.3148 0.035 Uiso 1 1 calc R . . . .
C14 C 0.46476(19) 0.1633(3) 0.40082(10) 0.0409(5) Uani 1 1 d . . . . .
H14A H 0.3811 0.1018 0.3921 0.061 Uiso 1 1 calc GR . . . .
H14B H 0.4576 0.2574 0.4350 0.061 Uiso 1 1 calc GR . . . .
H14C H 0.5325 0.0800 0.4193 0.061 Uiso 1 1 calc GR . . . .
C15 C 1.27956(14) 0.6845(2) 0.44978(8) 0.0255(3) Uani 1 1 d . . . . .
H15A H 1.2523 0.6057 0.4106 0.038 Uiso 1 1 calc GR . . . .
H15B H 1.3562 0.6353 0.4777 0.038 Uiso 1 1 calc GR . . . .
H15C H 1.3014 0.8000 0.4317 0.038 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2210(17) . ?
N1 C1 1.3602(17) . ?
N1 C8 1.4832(17) . ?
N1 C11 1.4678(17) . ?
C1 C2 1.5424(19) . ?
O2 C12 1.1990(19) . ?
C2 H2 0.9800 . ?
C2 C3 1.5388(19) . ?
C2 C12 1.5124(19) . ?
O3 C12 1.3328(19) . ?
O3 C13 1.4550(18) . ?
C3 H3 0.9800 . ?
C3 C4 1.5267(19) . ?
C3 C8 1.5374(18) . ?
O4 C5 1.2176(17) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.506(2) . ?
O5 C6 1.3656(16) . ?
O5 C15 1.4289(18) . ?
C5 C6 1.4866(19) . ?
C6 C7 1.3386(19) . ?
C7 H7 0.9300 . ?
C7 C8 1.5070(19) . ?
C8 C9 1.5480(19) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.531(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.532(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.489(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 113.26(11) . . ?
C1 N1 C11 123.58(11) . . ?
C11 N1 C8 111.68(11) . . ?
O1 C1 N1 125.81(13) . . ?
O1 C1 C2 126.93(12) . . ?
N1 C1 C2 107.24(11) . . ?
C1 C2 H2 110.2 . . ?
C3 C2 C1 101.91(11) . . ?
C3 C2 H2 110.2 . . ?
C12 C2 C1 110.55(11) . . ?
C12 C2 H2 110.2 . . ?
C12 C2 C3 113.55(11) . . ?
C12 O3 C13 117.27(12) . . ?
C2 C3 H3 108.1 . . ?
C4 C3 C2 115.91(11) . . ?
C4 C3 H3 108.1 . . ?
C4 C3 C8 113.02(11) . . ?
C8 C3 C2 103.17(10) . . ?
C8 C3 H3 108.1 . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 C3 114.03(11) . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C6 O5 C15 115.64(11) . . ?
O4 C5 C4 121.92(13) . . ?
O4 C5 C6 121.81(13) . . ?
C6 C5 C4 116.23(12) . . ?
O5 C6 C5 112.02(12) . . ?
C7 C6 O5 125.97(13) . . ?
C7 C6 C5 122.01(12) . . ?
C6 C7 H7 117.8 . . ?
C6 C7 C8 124.36(12) . . ?
C8 C7 H7 117.8 . . ?
N1 C8 C3 102.38(10) . . ?
N1 C8 C7 109.54(11) . . ?
N1 C8 C9 103.46(10) . . ?
C3 C8 C9 116.04(11) . . ?
C7 C8 C3 112.76(11) . . ?
C7 C8 C9 111.62(11) . . ?
C8 C9 H9A 110.8 . . ?
C8 C9 H9B 110.8 . . ?
H9A C9 H9B 108.9 . . ?
C10 C9 C8 104.61(11) . . ?
C10 C9 H9A 110.8 . . ?
C10 C9 H9B 110.8 . . ?
C9 C10 H10A 111.1 . . ?
C9 C10 H10B 111.1 . . ?
C9 C10 C11 103.10(11) . . ?
H10A C10 H10B 109.1 . . ?
C11 C10 H10A 111.1 . . ?
C11 C10 H10B 111.1 . . ?
N1 C11 C10 101.38(11) . . ?
N1 C11 H11A 111.5 . . ?
N1 C11 H11B 111.5 . . ?
C10 C11 H11A 111.5 . . ?
C10 C11 H11B 111.5 . . ?
H11A C11 H11B 109.3 . . ?
O2 C12 C2 124.35(14) . . ?
O2 C12 O3 124.51(14) . . ?
O3 C12 C2 111.13(12) . . ?
O3 C13 H13A 109.3 . . ?
O3 C13 H13B 109.3 . . ?
O3 C13 C14 111.57(13) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O5 C15 H15A 109.5 . . ?
O5 C15 H15B 109.5 . . ?
O5 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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 C1 C2 C3 -153.11(13) . . . . ?
O1 C1 C2 C12 -32.11(19) . . . . ?
N1 C1 C2 C3 25.35(13) . . . . ?
N1 C1 C2 C12 146.36(12) . . . . ?
N1 C8 C9 C10 17.13(14) . . . . ?
C1 N1 C8 C3 -15.78(14) . . . . ?
C1 N1 C8 C7 104.11(13) . . . . ?
C1 N1 C8 C9 -136.75(11) . . . . ?
C1 N1 C11 C10 110.85(14) . . . . ?
C1 C2 C3 C4 -158.03(11) . . . . ?
C1 C2 C3 C8 -33.96(12) . . . . ?
C1 C2 C12 O2 -101.79(18) . . . . ?
C1 C2 C12 O3 76.84(14) . . . . ?
C2 C3 C4 C5 69.45(16) . . . . ?
C2 C3 C8 N1 30.59(12) . . . . ?
C2 C3 C8 C7 -87.02(13) . . . . ?
C2 C3 C8 C9 142.46(11) . . . . ?
C3 C2 C12 O2 12.0(2) . . . . ?
C3 C2 C12 O3 -169.35(11) . . . . ?
C3 C4 C5 O4 -149.73(13) . . . . ?
C3 C4 C5 C6 32.72(17) . . . . ?
C3 C8 C9 C10 -94.11(13) . . . . ?
O4 C5 C6 O5 -4.19(19) . . . . ?
O4 C5 C6 C7 176.29(13) . . . . ?
C4 C3 C8 N1 156.54(11) . . . . ?
C4 C3 C8 C7 38.92(16) . . . . ?
C4 C3 C8 C9 -91.60(14) . . . . ?
C4 C5 C6 O5 173.36(11) . . . . ?
C4 C5 C6 C7 -6.2(2) . . . . ?
O5 C6 C7 C8 176.80(13) . . . . ?
C5 C6 C7 C8 -3.8(2) . . . . ?
C6 C7 C8 N1 -126.57(14) . . . . ?
C6 C7 C8 C3 -13.26(19) . . . . ?
C6 C7 C8 C9 119.46(15) . . . . ?
C7 C8 C9 C10 134.83(12) . . . . ?
C8 N1 C1 O1 172.36(13) . . . . ?
C8 N1 C1 C2 -6.13(14) . . . . ?
C8 N1 C11 C10 -29.85(14) . . . . ?
C8 C3 C4 C5 -49.33(16) . . . . ?
C8 C9 C10 C11 -35.15(14) . . . . ?
C9 C10 C11 N1 39.09(13) . . . . ?
C11 N1 C1 O1 32.2(2) . . . . ?
C11 N1 C1 C2 -146.30(12) . . . . ?
C11 N1 C8 C3 129.17(11) . . . . ?
C11 N1 C8 C7 -110.94(12) . . . . ?
C11 N1 C8 C9 8.20(14) . . . . ?
C12 C2 C3 C4 83.08(15) . . . . ?
C12 C2 C3 C8 -152.85(11) . . . . ?
C12 O3 C13 C14 -90.83(18) . . . . ?
C13 O3 C12 O2 5.0(2) . . . . ?
C13 O3 C12 C2 -173.65(12) . . . . ?
C15 O5 C6 C5 164.78(12) . . . . ?
C15 O5 C6 C7 -15.7(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
7 4 20 0.1083 7.0217 4.0012 20.0282 -0.4044 -0.1824 -0.9224
6 -4 19 0.1067 6.0222 -4.0120 19.0003 0.0119 -0.7410 -0.6012
-1 -10 -2 0.1452 -0.9991 -10.0157 -2.0401 0.4992 -0.7004 0.4254
-6 -5 -19 0.1333 -6.0186 -5.0023 -19.0379 0.4020 0.0562 0.9104
-1 10 -4 0.1189 -1.0077 10.0174 -3.9643 -0.4388 0.8424 -0.1910
-5 6 19 0.1427 -5.0092 5.9913 19.1445 0.1845 0.4559 -0.8240
14 3 -2 0.0604 14.0330 3.0221 -2.1256 -0.9612 -0.3056 -0.1860
-14 -2 5 0.1134 -14.0325 -2.0225 5.1413 0.9425 0.3503 0.0454
12 -3 -15 0.0909 12.0265 -2.9812 -15.1819 -0.6886 -0.5469 0.5024
-5 3 24 0.1246 -5.0065 2.9832 24.1512 0.3680 0.1753 -0.8979
0 -8 18 0.1152 0.0086 -8.0245 18.0357 0.5317 -0.7971 -0.3624
-4 10 -3 0.1145 -4.0149 10.0133 -2.9325 -0.2572 0.9509 -0.1934
3 2 -26 0.1151 2.9989 2.0237 -26.1194 -0.5011 0.3054 0.8189
6 -9 -12 0.1276 6.0149 -8.9995 -12.1395 -0.0403 -0.7970 0.6682
-13 -1 -7 0.1122 -13.0340 -1.0118 -6.9099 0.7298 0.5124 0.4250
0 -1 26 0.1143 0.0082 -1.0187 26.0956 0.2826 -0.3482 -0.8862
-14 1 -5 0.1037 -14.0367 0.9889 -4.8846 0.7135 0.6833 0.2964
13 0 7 0.0631 13.0344 0.0102 6.9057 -0.6838 -0.5885 -0.3906

_olex2_date_sample_data_collection 2015-10-12
_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_eo200p_a
_database_code_depnum_ccdc_archive 'CCDC 2174967'
loop_
_audit_author_name
_audit_author_address
'Christopher Pask'
;University of Leeds
United Kingdom
;
_audit_update_record             
;
2022-05-25 deposited with the CCDC.	2022-12-12 downloaded from the CCDC.
;
_audit_creation_date             2019-01-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H20 N2 O4 S'
_chemical_formula_sum            'C17 H20 N2 O4 S'
_chemical_formula_weight         348.41
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C68  H80  N8  O16  S4  '
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'
S S 0.3331 0.5567 '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      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   8.51937(12)
_cell_length_b                   8.51937(12)
_cell_length_c                   22.6198(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1641.74(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2898
_cell_measurement_temperature    125.01(10)
_cell_measurement_theta_max      73.2990
_cell_measurement_theta_min      5.1570
_shelx_estimated_absorpt_T_max   0.891
_shelx_estimated_absorpt_T_min   0.731
_exptl_absorpt_coefficient_mu    1.967
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.673
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 4 -1 0.0301
-1 1 -14 0.0820
1 -1 14 0.0820
5 -2 -4 0.0337
-5 2 4 0.0337
-3 -5 -1 0.0167
1 -5 -2 0.0183

_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.9998 3.9969 -0.9996 0.3309 0.5391 0.6478
-0.9994 0.9992 -13.9945 -0.1083 0.8461 -0.4975
0.9994 -0.9992 13.9945 0.1083 -0.8461 0.4975
4.9928 -2.0036 -4.0036 0.9939 0.0607 -0.1754
-4.9928 2.0036 4.0036 -0.9939 -0.0607 0.1754
-3.0008 -4.9969 -1.0004 -0.2659 -0.5432 -0.8643
0.9949 -4.9999 -2.0030 0.4333 -0.4346 -0.6997

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            6158
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.446
_diffrn_reflns_theta_min         5.192
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      125.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00  27.00   1.00    1.00    --  -41.04  37.00 -60.00   55
  2  ω   -104.00 -14.00   1.00    1.00    --  -41.04 -57.00   0.00   90
  3  ω     45.00 102.00   1.00    1.00    --   41.04  37.00 -90.00   57
  4  ω     82.00 178.00   1.00    2.00    --  106.02  45.00  30.00   96
  5  ω     81.00 160.00   1.00    2.00    --  106.02  45.00 -60.00   79
  6  ω     80.00 108.00   1.00    2.00    --  106.02  45.00 -90.00   28
  7  ω     58.00  89.00   1.00    2.00    --  106.02 -45.00-180.00   31
  8  ω    116.00 141.00   1.00    2.00    --  106.02  45.00 -90.00   25
  9  ω    111.00 169.00   1.00    2.00    --  106.02  45.00-180.00   58
 10  ω     39.00 131.00   1.00    2.00    --  106.02 -30.00  90.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1729003000
_diffrn_orient_matrix_UB_12      -0.0490013000
_diffrn_orient_matrix_UB_13      -0.0081079000
_diffrn_orient_matrix_UB_21      0.0138361000
_diffrn_orient_matrix_UB_22      0.1111170000
_diffrn_orient_matrix_UB_23      -0.0535120000
_diffrn_orient_matrix_UB_31      0.0516927000
_diffrn_orient_matrix_UB_32      0.1336374000
_diffrn_orient_matrix_UB_33      0.0414023000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.909
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.945
_reflns_number_gt                2868
_reflns_number_total             3188
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1214 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3188
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0419P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0892
_refine_special_details          ?
_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:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
S1 S 0.50727(12) 0.02456(9) 0.46057(4) 0.02182(19) Uani 1 1 d . . . . .
O1 O 0.3243(3) 0.2795(3) 0.39706(10) 0.0275(6) Uani 1 1 d . . . . .
O2 O 0.9059(4) 0.4406(4) 0.42719(13) 0.0388(7) Uani 1 1 d . . . . .
O3 O 0.4825(4) -0.0215(4) 0.40067(12) 0.0313(7) Uani 1 1 d . . . . .
O4 O 0.6393(3) -0.0340(3) 0.49292(12) 0.0287(6) Uani 1 1 d . . . . .
N1 N 0.4261(4) 0.4610(3) 0.46247(13) 0.0209(6) Uani 1 1 d . . . . .
N2 N 0.5276(4) 0.2185(3) 0.46239(12) 0.0201(6) Uani 1 1 d . . . . .
C1 C 0.2833(5) 0.5573(5) 0.46782(17) 0.0283(8) Uani 1 1 d . . . . .
H1A H 0.2001 0.5164 0.4429 0.034 Uiso 1 1 calc R . . . .
H1B H 0.3042 0.6652 0.4567 0.034 Uiso 1 1 calc R . . . .
C2 C 0.2381(6) 0.5461(6) 0.53336(18) 0.0371(10) Uani 1 1 d . . . . .
H2A H 0.2365 0.6497 0.5512 0.045 Uiso 1 1 calc R . . . .
H2B H 0.1349 0.4994 0.5376 0.045 Uiso 1 1 calc R . . . .
C3 C 0.3625(5) 0.4432(5) 0.56310(16) 0.0251(8) Uani 1 1 d . . . . .
H3A H 0.3245 0.3366 0.5680 0.030 Uiso 1 1 calc R . . . .
H3B H 0.3906 0.4849 0.6016 0.030 Uiso 1 1 calc R . . . .
C4 C 0.5033(4) 0.4476(4) 0.52097(15) 0.0194(7) Uani 1 1 d . . . . .
C5 C 0.6120(5) 0.5878(4) 0.53186(16) 0.0248(8) Uani 1 1 d . . . . .
H5A H 0.5498 0.6831 0.5339 0.030 Uiso 1 1 calc R . . . .
H5B H 0.6648 0.5745 0.5695 0.030 Uiso 1 1 calc R . . . .
C6 C 0.7346(5) 0.6045(5) 0.48287(16) 0.0277(8) Uani 1 1 d . . . . .
H6A H 0.6840 0.6450 0.4476 0.033 Uiso 1 1 calc R . . . .
H6B H 0.8131 0.6803 0.4951 0.033 Uiso 1 1 calc R . . . .
C7 C 0.8146(5) 0.4520(4) 0.46815(15) 0.0246(8) Uani 1 1 d . . . . .
C8 C 0.7761(4) 0.3159(4) 0.50832(14) 0.0218(7) Uani 1 1 d . . . . .
H8A H 0.8234 0.3339 0.5467 0.026 Uiso 1 1 calc R . . . .
H8B H 0.8214 0.2208 0.4921 0.026 Uiso 1 1 calc R . . . .
C9 C 0.5988(4) 0.2930(4) 0.51594(14) 0.0182(7) Uani 1 1 d . . . . .
H9 H 0.5787 0.2272 0.5507 0.022 Uiso 1 1 calc R . . . .
C10 C 0.4141(4) 0.3168(4) 0.43659(14) 0.0205(7) Uani 1 1 d . . . . .
C11 C 0.3357(4) -0.0111(4) 0.50191(15) 0.0200(7) Uani 1 1 d . . . . .
C12 C 0.1913(4) -0.0191(4) 0.47317(15) 0.0218(7) Uani 1 1 d . . . . .
H12 H 0.1854 -0.0091 0.4323 0.026 Uiso 1 1 calc R . . . .
C13 C 0.0568(5) -0.0422(4) 0.50630(15) 0.0232(8) Uani 1 1 d . . . . .
H13 H -0.0396 -0.0483 0.4872 0.028 Uiso 1 1 calc R . . . .
C14 C 0.0621(5) -0.0565(5) 0.56787(16) 0.0250(8) Uani 1 1 d . . . . .
C15 C 0.2070(5) -0.0467(5) 0.59530(16) 0.0269(8) Uani 1 1 d . . . . .
H15 H 0.2120 -0.0548 0.6363 0.032 Uiso 1 1 calc R . . . .
C16 C 0.3452(5) -0.0251(5) 0.56362(16) 0.0246(8) Uani 1 1 d . . . . .
H16 H 0.4416 -0.0200 0.5829 0.030 Uiso 1 1 calc R . . . .
C17 C -0.0858(5) -0.0849(6) 0.60259(18) 0.0325(9) Uani 1 1 d . . . . .
H17A H -0.1283 0.0137 0.6155 0.049 Uiso 1 1 calc GR . . . .
H17B H -0.0625 -0.1488 0.6364 0.049 Uiso 1 1 calc GR . . . .
H17C H -0.1611 -0.1377 0.5781 0.049 Uiso 1 1 calc GR . . . .


_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
S1 O3 1.426(3) . ?
S1 O4 1.432(3) . ?
S1 N2 1.661(3) . ?
S1 C11 1.761(4) . ?
O1 C10 1.219(4) . ?
O2 C7 1.214(5) . ?
N1 C1 1.472(5) . ?
N1 C4 1.482(5) . ?
N1 C10 1.364(5) . ?
N2 C9 1.496(4) . ?
N2 C10 1.407(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.535(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.531(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.533(5) . ?
C4 C5 1.531(5) . ?
C4 C9 1.552(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.530(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.505(6) . ?
C7 C8 1.509(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.533(5) . ?
C9 H9 0.9800 . ?
C11 C12 1.393(5) . ?
C11 C16 1.403(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.383(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.399(5) . ?
C14 C15 1.384(6) . ?
C14 C17 1.505(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.391(6) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
O3 S1 O4 120.37(18) . . ?
O3 S1 N2 108.23(16) . . ?
O3 S1 C11 109.52(18) . . ?
O4 S1 N2 104.59(16) . . ?
O4 S1 C11 108.69(17) . . ?
N2 S1 C11 104.17(16) . . ?
C1 N1 C4 109.6(3) . . ?
C10 N1 C1 118.3(3) . . ?
C10 N1 C4 110.3(3) . . ?
C9 N2 S1 119.0(2) . . ?
C10 N2 S1 120.7(2) . . ?
C10 N2 C9 111.2(3) . . ?
N1 C1 H1A 110.8 . . ?
N1 C1 H1B 110.8 . . ?
N1 C1 C2 104.6(3) . . ?
H1A C1 H1B 108.9 . . ?
C2 C1 H1A 110.8 . . ?
C2 C1 H1B 110.8 . . ?
C1 C2 H2A 110.4 . . ?
C1 C2 H2B 110.4 . . ?
H2A C2 H2B 108.6 . . ?
C3 C2 C1 106.6(3) . . ?
C3 C2 H2A 110.4 . . ?
C3 C2 H2B 110.4 . . ?
C2 C3 H3A 110.8 . . ?
C2 C3 H3B 110.8 . . ?
C2 C3 C4 104.7(3) . . ?
H3A C3 H3B 108.9 . . ?
C4 C3 H3A 110.8 . . ?
C4 C3 H3B 110.8 . . ?
N1 C4 C3 102.1(3) . . ?
N1 C4 C5 110.6(3) . . ?
N1 C4 C9 103.4(3) . . ?
C3 C4 C9 115.8(3) . . ?
C5 C4 C3 113.1(3) . . ?
C5 C4 C9 110.9(3) . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 C4 111.7(3) . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C5 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 C5 112.9(3) . . ?
C7 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
O2 C7 C6 121.9(3) . . ?
O2 C7 C8 122.5(4) . . ?
C6 C7 C8 115.6(3) . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
C7 C8 C9 112.3(3) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
N2 C9 C4 102.0(3) . . ?
N2 C9 C8 111.2(3) . . ?
N2 C9 H9 109.6 . . ?
C4 C9 H9 109.6 . . ?
C8 C9 C4 114.6(3) . . ?
C8 C9 H9 109.6 . . ?
O1 C10 N1 126.6(3) . . ?
O1 C10 N2 125.5(3) . . ?
N1 C10 N2 107.9(3) . . ?
C12 C11 S1 119.6(3) . . ?
C12 C11 C16 120.7(3) . . ?
C16 C11 S1 119.7(3) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 119.0(3) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 H13 119.2 . . ?
C12 C13 C14 121.7(3) . . ?
C14 C13 H13 119.2 . . ?
C13 C14 C17 120.5(4) . . ?
C15 C14 C13 118.0(4) . . ?
C15 C14 C17 121.5(3) . . ?
C14 C15 H15 118.9 . . ?
C14 C15 C16 122.1(3) . . ?
C16 C15 H15 118.9 . . ?
C11 C16 H16 120.8 . . ?
C15 C16 C11 118.4(3) . . ?
C15 C16 H16 120.8 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?


_olex2_date_sample_data_collection 2019-01-11
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.207
_oxdiff_exptl_absorpt_empirical_full_min 0.928
####################################################################### 
# 
# 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_eo303p
_database_code_depnum_ccdc_archive 'CCDC 2175094'
loop_
_audit_author_name
_audit_author_address
'Christopher Pask'
;University of Leeds
United Kingdom
;
_audit_update_record             
;
2022-05-26 deposited with the CCDC.	2022-12-12 downloaded from the CCDC.
;
_audit_creation_date             2019-01-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H26 F N3 O3'
_chemical_formula_sum            'C20 H26 F N3 O3'
_chemical_formula_weight         375.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C80  H104  F4  N12  O12  '
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'
F F 0.0727 0.0534 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.6465(3)
_cell_length_b                   19.7846(5)
_cell_length_c                   8.73330(19)
_cell_angle_alpha                90
_cell_angle_beta                 103.566(2)
_cell_angle_gamma                90
_cell_volume                     1956.20(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3546
_cell_measurement_temperature    120.00(18)
_cell_measurement_theta_max      73.3210
_cell_measurement_theta_min      4.0040
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.900
_exptl_absorpt_coefficient_mu    0.766
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.843
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 13 1 0.0288
-1 -13 -1 0.0288
-7 2 3 0.0508
-6 7 0 0.0356
6 -7 0 0.0356
0 3 -5 0.0538
0 -3 5 0.0538
1 12 -1 0.0307
-1 -13 0 0.0288

_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0042 13.0011 1.0024 0.3634 0.9778 0.0073
-1.0042 -13.0011 -1.0024 -0.3634 -0.9778 -0.0073
-6.9965 2.0081 2.9997 -0.4074 0.2646 -0.8652
-5.9967 7.0099 0.0005 0.2457 0.3313 -0.8913
5.9967 -7.0099 -0.0005 -0.2457 -0.3313 0.8913
-0.0016 3.0041 -4.9998 0.8715 -0.2785 -0.2015
0.0016 -3.0041 4.9998 -0.8715 0.2785 0.2015
1.0029 12.0022 -0.9979 0.6258 0.7208 -0.0462
-1.0037 -13.0018 -0.0023 -0.5142 -0.8824 0.0256

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8404
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.454
_diffrn_reflns_theta_min         3.904
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  32.00   1.00    1.00    --  -41.04  37.00   0.00   56
  2  ω    -21.00  30.00   1.00    1.00    --  -41.04  57.00 120.00   51
  3  ω    -68.00  31.00   1.00    1.00    --  -41.04  57.00  60.00   99
  4  ω     43.00  69.00   1.00    1.00    --   41.04 -57.00  30.00   26
  5  ω     15.00  78.00   1.00    1.00    --   41.04  65.00  88.24   63
  6  ω     67.00 105.00   1.00    4.00    --  106.02 -65.00 -17.98   38
  7  ω     26.00 151.00   1.00    4.00    --  106.02 -15.00 -60.00  125
  8  ω     86.00 177.00   1.00    4.00    --  106.02  45.00 120.00   91
  9  ω     34.00 131.00   1.00    4.00    --  106.02 -65.00  35.66   97
 10  ω     56.00  83.00   1.00    4.00    --  106.02 -65.00 -37.16   27
 11  ω     46.00 105.00   1.00    4.00    --  106.02 -63.00 -60.67   59
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0048455000
_diffrn_orient_matrix_UB_12      0.0392025000
_diffrn_orient_matrix_UB_13      -0.1507447000
_diffrn_orient_matrix_UB_21      0.0220761000
_diffrn_orient_matrix_UB_22      0.0661432000
_diffrn_orient_matrix_UB_23      0.0954273000
_diffrn_orient_matrix_UB_31      0.1342070000
_diffrn_orient_matrix_UB_32      -0.0123351000
_diffrn_orient_matrix_UB_33      0.0328450000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3084
_reflns_number_total             3763
_reflns_odcompleteness_completeness 98.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3763
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0411P)²+0.5017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1021
_refine_special_details          ?
_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:
 C6(H6), C7(H7), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C10(H10A,H10B), C11(H11A,H11B),
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C18(H18), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
F1 F 0.64151(9) 0.18948(7) 1.26207(13) 0.0463(3) Uani 1 1 d . . . . .
O1 O -0.04385(9) -0.11741(6) 0.10352(12) 0.0246(2) Uani 1 1 d . . . . .
O2 O 0.24350(9) 0.03613(6) 0.71719(12) 0.0261(2) Uani 1 1 d . . . . .
O3 O 0.43661(10) 0.05903(6) 0.82519(13) 0.0304(3) Uani 1 1 d . . . . .
N1 N 0.12839(11) -0.05361(6) 0.18082(14) 0.0210(3) Uani 1 1 d . . . . .
N2 N 0.09290(11) -0.13707(6) 0.33679(14) 0.0212(3) Uani 1 1 d . . . . .
N3 N 0.28583(12) 0.10551(7) 0.92021(15) 0.0233(3) Uani 1 1 d . . . . .
H3 H 0.2091(19) 0.1075(11) 0.901(2) 0.033(5) Uiso 1 1 d . . . . .
C1 C 0.04953(13) -0.10413(7) 0.19992(17) 0.0200(3) Uani 1 1 d . . . . .
C2 C 0.14537(14) -0.04559(9) 0.01953(18) 0.0272(3) Uani 1 1 d . . . . .
H2A H 0.1526 0.0018 -0.0052 0.033 Uiso 1 1 calc R . . . .
H2B H 0.0795 -0.0649 -0.0571 0.033 Uiso 1 1 calc R . . . .
C3 C 0.26135(14) -0.08419(8) 0.01963(18) 0.0261(3) Uani 1 1 d . . . . .
H3A H 0.2481 -0.1180 -0.0632 0.031 Uiso 1 1 calc R . . . .
H3B H 0.3220 -0.0532 0.0036 0.031 Uiso 1 1 calc R . . . .
C4 C 0.29820(13) -0.11784(8) 0.18257(18) 0.0226(3) Uani 1 1 d . . . . .
H4A H 0.3835 -0.1197 0.2189 0.027 Uiso 1 1 calc R . . . .
H4B H 0.2665 -0.1633 0.1805 0.027 Uiso 1 1 calc R . . . .
C5 C 0.24355(13) -0.07088(7) 0.28754(17) 0.0202(3) Uani 1 1 d . . . . .
C6 C 0.20388(13) -0.10655(7) 0.42318(17) 0.0205(3) Uani 1 1 d . . . . .
H6 H 0.2607 -0.1417 0.4698 0.025 Uiso 1 1 calc R . . . .
C7 C 0.02741(14) -0.19225(8) 0.38953(18) 0.0239(3) Uani 1 1 d . . . . .
H7 H -0.0261 -0.2109 0.2954 0.029 Uiso 1 1 calc R . . . .
C8 C -0.04887(17) -0.16852(10) 0.4985(2) 0.0391(4) Uani 1 1 d . . . . .
H8A H 0.0009 -0.1532 0.5961 0.059 Uiso 1 1 calc GR . . . .
H8B H -0.0971 -0.2053 0.5186 0.059 Uiso 1 1 calc GR . . . .
H8C H -0.0986 -0.1321 0.4496 0.059 Uiso 1 1 calc GR . . . .
C9 C 0.11067(16) -0.24821(9) 0.4613(2) 0.0389(4) Uani 1 1 d . . . . .
H9A H 0.1592 -0.2603 0.3906 0.058 Uiso 1 1 calc GR . . . .
H9B H 0.0659 -0.2869 0.4796 0.058 Uiso 1 1 calc GR . . . .
H9C H 0.1599 -0.2331 0.5594 0.058 Uiso 1 1 calc GR . . . .
C10 C 0.32450(14) -0.00971(8) 0.33763(18) 0.0249(3) Uani 1 1 d . . . . .
H10A H 0.4040 -0.0258 0.3822 0.030 Uiso 1 1 calc R . . . .
H10B H 0.3267 0.0166 0.2447 0.030 Uiso 1 1 calc R . . . .
C11 C 0.28718(15) 0.03641(8) 0.45740(19) 0.0271(3) Uani 1 1 d . . . . .
H11A H 0.3450 0.0721 0.4893 0.033 Uiso 1 1 calc R . . . .
H11B H 0.2115 0.0571 0.4109 0.033 Uiso 1 1 calc R . . . .
C12 C 0.27810(14) -0.00556(8) 0.59873(18) 0.0244(3) Uani 1 1 d . . . . .
H12 H 0.3538 -0.0277 0.6436 0.029 Uiso 1 1 calc R . . . .
C13 C 0.18143(14) -0.05824(8) 0.55182(17) 0.0237(3) Uani 1 1 d . . . . .
H13A H 0.1063 -0.0356 0.5135 0.028 Uiso 1 1 calc R . . . .
H13B H 0.1763 -0.0844 0.6440 0.028 Uiso 1 1 calc R . . . .
C14 C 0.33321(13) 0.06670(8) 0.82195(17) 0.0221(3) Uani 1 1 d . . . . .
C15 C 0.34788(14) 0.14204(8) 1.05139(17) 0.0218(3) Uani 1 1 d . . . . .
C16 C 0.47034(14) 0.14604(8) 1.09439(18) 0.0250(3) Uani 1 1 d . . . . .
H16 H 0.5166 0.1233 1.0375 0.030 Uiso 1 1 calc R . . . .
C17 C 0.52116(15) 0.18456(9) 1.22340(19) 0.0299(4) Uani 1 1 d . . . . .
C18 C 0.45856(18) 0.21884(11) 1.3137(2) 0.0423(5) Uani 1 1 d . . . . .
H18 H 0.4963 0.2446 1.4000 0.051 Uiso 1 1 calc R . . . .
C19 C 0.33677(18) 0.21338(11) 1.2704(2) 0.0454(5) Uani 1 1 d . . . . .
H19 H 0.2916 0.2353 1.3301 0.055 Uiso 1 1 calc R . . . .
C20 C 0.28066(16) 0.17602(9) 1.1405(2) 0.0325(4) Uani 1 1 d . . . . .
H20 H 0.1987 0.1735 1.1126 0.039 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
F1 C17 1.366(2) . ?
O1 C1 1.2373(18) . ?
O2 C12 1.4521(18) . ?
O2 C14 1.3587(18) . ?
O3 C14 1.2075(19) . ?
N1 C1 1.3938(19) . ?
N1 C2 1.4762(19) . ?
N1 C5 1.4825(19) . ?
N2 C1 1.3511(19) . ?
N2 C6 1.4652(18) . ?
N2 C7 1.4664(19) . ?
N3 H3 0.87(2) . ?
N3 C14 1.361(2) . ?
N3 C15 1.4031(19) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.551(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.538(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.544(2) . ?
C5 C6 1.540(2) . ?
C5 C10 1.533(2) . ?
C6 H6 0.9800 . ?
C6 C13 1.543(2) . ?
C7 H7 0.9800 . ?
C7 C8 1.521(2) . ?
C7 C9 1.508(2) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.526(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.512(2) . ?
C12 H12 0.9800 . ?
C12 C13 1.518(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C15 C16 1.389(2) . ?
C15 C20 1.399(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.374(2) . ?
C17 C18 1.372(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.384(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.383(3) . ?
C20 H20 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
C14 O2 C12 115.76(12) . . ?
C1 N1 C2 115.52(12) . . ?
C1 N1 C5 106.49(12) . . ?
C2 N1 C5 108.71(11) . . ?
C1 N2 C6 111.00(12) . . ?
C1 N2 C7 121.52(13) . . ?
C6 N2 C7 127.30(12) . . ?
C14 N3 H3 117.1(13) . . ?
C14 N3 C15 126.72(14) . . ?
C15 N3 H3 116.2(13) . . ?
O1 C1 N1 124.72(14) . . ?
O1 C1 N2 125.88(14) . . ?
N2 C1 N1 109.37(12) . . ?
N1 C2 H2A 110.8 . . ?
N1 C2 H2B 110.8 . . ?
N1 C2 C3 104.95(12) . . ?
H2A C2 H2B 108.8 . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C2 C3 H3A 110.6 . . ?
C2 C3 H3B 110.6 . . ?
H3A C3 H3B 108.8 . . ?
C4 C3 C2 105.52(12) . . ?
C4 C3 H3A 110.6 . . ?
C4 C3 H3B 110.6 . . ?
C3 C4 H4A 111.2 . . ?
C3 C4 H4B 111.2 . . ?
C3 C4 C5 102.97(12) . . ?
H4A C4 H4B 109.1 . . ?
C5 C4 H4A 111.2 . . ?
C5 C4 H4B 111.2 . . ?
N1 C5 C4 101.75(11) . . ?
N1 C5 C6 101.47(11) . . ?
N1 C5 C10 113.73(12) . . ?
C6 C5 C4 114.89(12) . . ?
C10 C5 C4 109.45(12) . . ?
C10 C5 C6 114.68(12) . . ?
N2 C6 C5 100.39(11) . . ?
N2 C6 H6 110.5 . . ?
N2 C6 C13 110.52(12) . . ?
C5 C6 H6 110.5 . . ?
C5 C6 C13 114.12(12) . . ?
C13 C6 H6 110.5 . . ?
N2 C7 H7 107.0 . . ?
N2 C7 C8 112.95(13) . . ?
N2 C7 C9 110.25(13) . . ?
C8 C7 H7 107.0 . . ?
C9 C7 H7 107.0 . . ?
C9 C7 C8 112.31(15) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 108.7 . . ?
C5 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 C5 114.36(12) . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C10 C11 H11A 110.0 . . ?
C10 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
C12 C11 C10 108.47(13) . . ?
C12 C11 H11A 110.0 . . ?
C12 C11 H11B 110.0 . . ?
O2 C12 C11 110.73(13) . . ?
O2 C12 H12 110.0 . . ?
O2 C12 C13 105.67(12) . . ?
C11 C12 H12 110.0 . . ?
C11 C12 C13 110.26(13) . . ?
C13 C12 H12 110.0 . . ?
C6 C13 H13A 109.1 . . ?
C6 C13 H13B 109.1 . . ?
C12 C13 C6 112.34(12) . . ?
C12 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
O2 C14 N3 108.31(13) . . ?
O3 C14 O2 124.40(14) . . ?
O3 C14 N3 127.28(14) . . ?
C16 C15 N3 123.34(14) . . ?
C16 C15 C20 119.69(15) . . ?
C20 C15 N3 116.97(14) . . ?
C15 C16 H16 121.0 . . ?
C17 C16 C15 118.08(15) . . ?
C17 C16 H16 121.0 . . ?
F1 C17 C16 117.51(15) . . ?
F1 C17 C18 118.38(15) . . ?
C18 C17 C16 124.10(16) . . ?
C17 C18 H18 121.5 . . ?
C17 C18 C19 116.95(16) . . ?
C19 C18 H18 121.5 . . ?
C18 C19 H19 119.2 . . ?
C20 C19 C18 121.50(17) . . ?
C20 C19 H19 119.2 . . ?
C15 C20 H20 120.2 . . ?
C19 C20 C15 119.66(17) . . ?
C19 C20 H20 120.2 . . ?


_olex2_date_sample_data_collection 2019-01-03
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.159
_oxdiff_exptl_absorpt_empirical_full_min 0.938
####################################################################### 
# 
# 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_eo104p
_database_code_depnum_ccdc_archive 'CCDC 2174963'
loop_
_audit_author_name
_audit_author_address
'Christopher Pask'
;University of Leeds
United Kingdom
;
_audit_update_record             
;
2022-05-25 deposited with the CCDC.	2022-12-12 downloaded from the CCDC.
;
_audit_creation_date             2019-03-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H20 N2 O2'
_chemical_formula_sum            'C13 H20 N2 O2'
_chemical_formula_weight         236.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C52  H80  N8  O8  '
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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.3232(2)
_cell_length_b                   15.4039(3)
_cell_length_c                   9.4930(2)
_cell_angle_alpha                90
_cell_angle_beta                 114.951(3)
_cell_angle_gamma                90
_cell_volume                     1236.08(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5732
_cell_measurement_temperature    125.01(10)
_cell_measurement_theta_max      73.3160
_cell_measurement_theta_min      5.7400
_shelx_estimated_absorpt_T_max   0.928
_shelx_estimated_absorpt_T_min   0.825
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.623
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             512
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 2 5 0.0565
5 1 1 0.0659
-4 -1 -3 0.1063
0 0 -6 0.1216
2 10 0 0.1204
-1 -8 4 0.0804
-2 -10 1 0.1351
5 0 -5 0.0595
-4 6 0 0.1199
5 -5 -2 0.0822
-5 -1 5 0.0445

_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5.0000 2.0000 5.0000 -0.0814 0.9808 -0.1251
5.0000 1.0000 1.0000 -0.4048 -0.5134 -0.7629
-4.0000 -1.0000 -3.0000 0.4166 0.2537 0.9598
-0.0000 0.0000 -6.0000 0.2010 -0.4195 0.9676
2.0000 10.0000 0.0000 -1.0614 -0.0800 0.0145
-1.0000 -8.0000 4.0000 0.6820 0.2718 -0.7321
-2.0000 -10.0000 1.0000 1.0279 0.1499 -0.1758
5.0000 0.0000 -5.0000 -0.1088 -0.9489 0.1782
-4.0000 6.0000 0.0000 -0.3496 0.5753 0.6620
5.0000 -5.0000 -2.0000 0.2662 -0.8190 -0.4385
-5.0000 -1.0000 5.0000 0.2038 0.9329 -0.2048

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9586
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.541
_diffrn_reflns_theta_min         5.745
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      125.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -112.00 -60.00   1.00    1.00    --  -41.04 -57.00 -60.00   52
  2  ω    -43.00 -13.00   1.00    1.00    --  -41.04 -57.00 -90.00   30
  3  ω    -45.00  32.00   1.00    1.00    --  -41.04  37.00  90.00   77
  4  ω    -64.00  25.00   1.00    1.00    --  -41.04  37.00  30.00   89
  5  ω   -111.00 -22.00   1.00    1.00    --  -41.04 -57.00   0.00   89
  6  ω   -101.00 -67.00   1.00    1.00    --  -41.04 -57.00 -90.00   34
  7  ω     40.00  69.00   1.00    1.00    --   41.04 -57.00 -90.00   29
  8  ω     52.00  78.00   1.00    1.00    --   41.04  57.00   0.00   26
  9  ω     55.00 128.00   1.00    1.00    --  106.02 -15.00 -90.00   73
 10  ω     81.00 108.00   1.00    1.00    --  106.02  30.00   0.00   27
 11  ω     25.00  52.00   1.00    1.00    --  106.02 -15.00 -90.00   27
 12  ω     64.00 103.00   1.00    1.00    --  106.02 -65.00-113.99   39
 13  ω     96.00 144.00   1.00    1.00    --  106.02  45.00 150.00   48
 14  ω     77.00 163.00   1.00    1.00    --  106.02  61.00   0.00   86
 15  ω     94.00 177.00   1.00    1.00    --  106.02  30.00  90.00   83
 16  ω     81.00 118.00   1.00    1.00    --  106.02  45.00   0.00   37
 17  ω     34.00  95.00   1.00    1.00    --  106.02 -65.00  17.17   61
 18  ω    128.00 173.00   1.00    1.00    --  106.02  61.00 -30.00   45
 19  ω     78.00 178.00   1.00    1.00    --  106.02  61.00  30.00  100
 20  ω     76.00 103.00   1.00    1.00    --  106.02 -64.00  34.09   27
 21  ω     77.00 103.00   1.00    1.00    --  106.02  61.00 -30.00   26
 22  ω     35.00 129.00   1.00    1.00    --  106.02 -63.00-168.32   94
 23  ω     61.00  90.00   1.00    1.00    --  106.02 -65.00-126.78   29
 24  ω     41.00 106.00   1.00    1.00    --  106.02 -65.00 -48.86   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0552494000
_diffrn_orient_matrix_UB_12      -0.0950945000
_diffrn_orient_matrix_UB_13      -0.0334993000
_diffrn_orient_matrix_UB_21      -0.1198632000
_diffrn_orient_matrix_UB_22      0.0159695000
_diffrn_orient_matrix_UB_23      0.0699115000
_diffrn_orient_matrix_UB_31      -0.1256331000
_diffrn_orient_matrix_UB_32      0.0265749000
_diffrn_orient_matrix_UB_33      -0.1612743000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2188
_reflns_number_total             2433
_reflns_odcompleteness_completeness 99.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0433P)²+0.5498P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0964
_refine_special_details          ?
_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:
 C6(H6), C8(H8), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
O1 O 0.63381(11) 0.43109(6) 0.85153(11) 0.0275(2) Uani 1 1 d . . . . .
O2 O 0.48368(11) 0.72399(6) 0.30388(11) 0.0269(2) Uani 1 1 d . . . . .
N1 N 0.74407(12) 0.48367(7) 0.68925(13) 0.0214(2) Uani 1 1 d . . . . .
N2 N 0.64794(12) 0.57744(6) 0.80790(12) 0.0193(2) Uani 1 1 d . . . . .
C1 C 0.67103(14) 0.49223(8) 0.78947(14) 0.0207(3) Uani 1 1 d . . . . .
C2 C 0.87054(16) 0.41856(9) 0.72754(17) 0.0282(3) Uani 1 1 d . . . . .
H2A H 0.8595 0.3868 0.6353 0.034 Uiso 1 1 calc R . . . .
H2B H 0.8672 0.3777 0.8038 0.034 Uiso 1 1 calc R . . . .
C3 C 1.02737(16) 0.47053(9) 0.79428(16) 0.0265(3) Uani 1 1 d . . . . .
H3A H 1.0973 0.4491 0.8964 0.032 Uiso 1 1 calc R . . . .
H3B H 1.0809 0.4660 0.7264 0.032 Uiso 1 1 calc R . . . .
C4 C 0.97901(14) 0.56491(9) 0.80393(15) 0.0228(3) Uani 1 1 d . . . . .
H4A H 1.0474 0.6053 0.7829 0.027 Uiso 1 1 calc R . . . .
H4B H 0.9829 0.5774 0.9056 0.027 Uiso 1 1 calc R . . . .
C5 C 0.80805(14) 0.57007(8) 0.67706(14) 0.0191(3) Uani 1 1 d . . . . .
C6 C 0.69819(14) 0.63257(8) 0.71096(14) 0.0182(3) Uani 1 1 d . . . . .
H6 H 0.7582 0.6825 0.7709 0.022 Uiso 1 1 calc R . . . .
C7 C 0.55990(15) 0.66319(8) 0.56243(15) 0.0211(3) Uani 1 1 d . . . . .
H7A H 0.4921 0.6141 0.5134 0.025 Uiso 1 1 calc R . . . .
H7B H 0.4980 0.7052 0.5892 0.025 Uiso 1 1 calc R . . . .
C8 C 0.61477(15) 0.70428(8) 0.44740(15) 0.0224(3) Uani 1 1 d . . . . .
H8 H 0.6693 0.7587 0.4924 0.027 Uiso 1 1 calc R . . . .
C9 C 0.72991(16) 0.64534(9) 0.42211(16) 0.0263(3) Uani 1 1 d . . . . .
H9 H 0.7452 0.6523 0.3321 0.032 Uiso 1 1 calc R . . . .
C10 C 0.81057(15) 0.58410(9) 0.52120(15) 0.0247(3) Uani 1 1 d . . . . .
H10 H 0.8730 0.5473 0.4929 0.030 Uiso 1 1 calc R . . . .
C11 C 0.55639(15) 0.60541(8) 0.89391(15) 0.0226(3) Uani 1 1 d . . . . .
H11 H 0.5803 0.5646 0.9800 0.027 Uiso 1 1 calc R . . . .
C12 C 0.37828(16) 0.60157(11) 0.79510(18) 0.0355(4) Uani 1 1 d . . . . .
H12A H 0.3483 0.6462 0.7173 0.053 Uiso 1 1 calc GR . . . .
H12B H 0.3238 0.6103 0.8601 0.053 Uiso 1 1 calc GR . . . .
H12C H 0.3506 0.5458 0.7457 0.053 Uiso 1 1 calc GR . . . .
C13 C 0.60947(18) 0.69453(9) 0.96495(17) 0.0310(3) Uani 1 1 d . . . . .
H13A H 0.7220 0.6945 1.0251 0.046 Uiso 1 1 calc GR . . . .
H13B H 0.5581 0.7085 1.0309 0.046 Uiso 1 1 calc GR . . . .
H13C H 0.5819 0.7370 0.8837 0.046 Uiso 1 1 calc GR . . . .
H2 H 0.444(2) 0.6742(12) 0.251(2) 0.033(4) Uiso 1 1 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
O1 C1 1.2356(15) . ?
O2 C8 1.4274(15) . ?
O2 H2 0.904(18) . ?
N1 C1 1.3903(17) . ?
N1 C2 1.4720(16) . ?
N1 C5 1.4828(16) . ?
N2 C1 1.3534(16) . ?
N2 C6 1.4667(15) . ?
N2 C11 1.4727(16) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.549(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.5362(19) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.5420(17) . ?
C5 C6 1.5355(16) . ?
C5 C10 1.5053(17) . ?
C6 H6 0.9800 . ?
C6 C7 1.5294(17) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.5250(17) . ?
C8 H8 0.9800 . ?
C8 C9 1.5006(18) . ?
C9 H9 0.9300 . ?
C9 C10 1.3204(19) . ?
C10 H10 0.9300 . ?
C11 H11 0.9800 . ?
C11 C12 1.5253(19) . ?
C11 C13 1.5175(19) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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
C8 O2 H2 109.3(11) . . ?
C1 N1 C2 117.92(11) . . ?
C1 N1 C5 107.31(9) . . ?
C2 N1 C5 108.91(10) . . ?
C1 N2 C6 111.72(10) . . ?
C1 N2 C11 121.09(10) . . ?
C6 N2 C11 126.28(10) . . ?
O1 C1 N1 124.82(11) . . ?
O1 C1 N2 125.85(12) . . ?
N2 C1 N1 109.33(10) . . ?
N1 C2 H2A 110.6 . . ?
N1 C2 H2B 110.6 . . ?
N1 C2 C3 105.57(10) . . ?
H2A C2 H2B 108.8 . . ?
C3 C2 H2A 110.6 . . ?
C3 C2 H2B 110.6 . . ?
C2 C3 H3A 110.7 . . ?
C2 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
C4 C3 C2 105.27(10) . . ?
C4 C3 H3A 110.7 . . ?
C4 C3 H3B 110.7 . . ?
C3 C4 H4A 111.0 . . ?
C3 C4 H4B 111.0 . . ?
C3 C4 C5 103.59(10) . . ?
H4A C4 H4B 109.0 . . ?
C5 C4 H4A 111.0 . . ?
C5 C4 H4B 111.0 . . ?
N1 C5 C4 102.13(9) . . ?
N1 C5 C6 102.74(9) . . ?
N1 C5 C10 112.28(10) . . ?
C6 C5 C4 115.45(10) . . ?
C10 C5 C4 109.60(10) . . ?
C10 C5 C6 113.85(10) . . ?
N2 C6 C5 100.74(9) . . ?
N2 C6 H6 110.2 . . ?
N2 C6 C7 112.88(10) . . ?
C5 C6 H6 110.2 . . ?
C7 C6 C5 112.18(10) . . ?
C7 C6 H6 110.2 . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 C6 112.41(10) . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
O2 C8 C7 111.16(10) . . ?
O2 C8 H8 108.2 . . ?
O2 C8 C9 111.00(10) . . ?
C7 C8 H8 108.2 . . ?
C9 C8 C7 110.01(10) . . ?
C9 C8 H8 108.2 . . ?
C8 C9 H9 118.3 . . ?
C10 C9 C8 123.31(12) . . ?
C10 C9 H9 118.3 . . ?
C5 C10 H10 117.9 . . ?
C9 C10 C5 124.22(12) . . ?
C9 C10 H10 117.9 . . ?
N2 C11 H11 107.1 . . ?
N2 C11 C12 112.52(11) . . ?
N2 C11 C13 110.76(10) . . ?
C12 C11 H11 107.1 . . ?
C13 C11 H11 107.1 . . ?
C13 C11 C12 112.01(12) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?


_olex2_date_sample_data_collection 2019-03-13
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.191
_oxdiff_exptl_absorpt_empirical_full_min 0.868
####################################################################### 
# 
# 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_eo194p
_database_code_depnum_ccdc_archive 'CCDC 2174965'
loop_
_audit_author_name
_audit_author_address
'Christopher Pask'
;University of Leeds
United Kingdom
;
_audit_update_record             
;
2022-05-25 deposited with the CCDC.	2022-12-12 downloaded from the CCDC.
;
_audit_creation_date             2019-04-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H18 N2 O4 S, 0.06(H2 O)'
_chemical_formula_sum            'C17 H18.12 N2 O4.06 S'
_chemical_formula_weight         347.52
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C272  H290  N32  O65  S16  '
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'
S S 0.3331 0.5567 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.9810(18)
_cell_length_b                   8.5032(5)
_cell_length_c                   34.011(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.007(7)
_cell_angle_gamma                90
_cell_volume                     6355.9(8)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    1508
_cell_measurement_temperature    125.01(10)
_cell_measurement_theta_max      73.4040
_cell_measurement_theta_min      3.9680
_shelx_estimated_absorpt_T_max   0.923
_shelx_estimated_absorpt_T_min   0.663
_exptl_absorpt_coefficient_mu    2.037
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.744
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2922
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-11 0 15 0.0193
11 0 -15 0.0193
0 5 4 0.1033
0 -5 -4 0.1033
-8 0 -18 0.0174
8 0 18 0.0174

_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-10.9764 -0.0012 14.9970 0.2856 0.6769 0.7045
10.9764 0.0012 -14.9970 -0.2856 -0.6769 -0.7045
0.0053 5.0020 4.0033 -0.2250 0.7629 -0.4710
-0.0053 -5.0020 -4.0033 0.2250 -0.7629 0.4710
-8.0213 -0.0044 -17.9959 -0.8896 -0.2129 0.3988
8.0213 0.0044 17.9959 0.8896 0.2129 -0.3988

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0862
_diffrn_reflns_av_unetI/netI     0.1321
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            12352
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.543
_diffrn_reflns_theta_min         4.023
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      125.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -112.00 -16.00   1.00   30.00    --  -40.79 -37.00  30.00   96
  2  ω    -64.00  28.00   1.00   30.00    --  -40.79  37.00-150.00   92
  3  ω     30.00  88.00   1.00   30.00    --   40.79  19.00 -30.00   58
  4  ω     97.00 132.00   1.00  120.00    --  106.02 -45.00  30.00   35
  5  ω     95.00 178.00   1.00  120.00    --  106.02  30.00 120.00   83
  6  ω     44.00 108.00   1.00  120.00    --  106.02 -61.00  60.00   64
  7  ω     77.00 176.00   1.00  120.00    --  106.02  61.00-180.00   99
  8  ω     79.00 144.00   1.00  120.00    --  106.02  61.00-120.00   65
  9  ω     30.00  88.00   1.00  120.00    --  106.02 -30.00-120.00   58
 10  ω     33.00  63.00   1.00  120.00    --  106.02 -45.00  30.00   30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0258272000
_diffrn_orient_matrix_UB_12      -0.0753775000
_diffrn_orient_matrix_UB_13      0.0379393000
_diffrn_orient_matrix_UB_21      -0.0283181000
_diffrn_orient_matrix_UB_22      0.1329932000
_diffrn_orient_matrix_UB_23      0.0244221000
_diffrn_orient_matrix_UB_31      -0.0586798000
_diffrn_orient_matrix_UB_32      -0.0973121000
_diffrn_orient_matrix_UB_33      0.0040186000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3479
_reflns_number_total             6240
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         6240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1395
_refine_ls_R_factor_gt           0.0771
_refine_ls_restrained_S_all      1.038
_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)+(0.0671P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1679
_refine_ls_wR_factor_ref         0.2158
_refine_special_details          
;
Residual electron density was modelled as 0.125 molecules of water. 
Hydrogen atoms have not been added to the model but are included in the cif for final refinement and the oxygen atom was refined isotropically.
;
_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. Others
 Fixed Sof: O9(0.125)
3.a Ternary CH refined with riding coordinates:
 C2(H2), C19(H19)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C20(H20A,H20B), C24(H24A,
 H24B), C25(H25A,H25B), C26(H26A,H26B)
3.c Me refined with riding coordinates:
 C17(H17A,H17B,H17C)
3.d Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C12(H12), C13(H13), C15(H15), C16(H16), C22(H22), C23(H23),
 C29(H29), C30(H30), C32(H32), C33(H33)
3.e Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
S1 S 0.49632(6) 0.41686(14) 0.60041(4) 0.0327(3) Uani 1 1 d . . . . .
O1 O 0.47495(18) 0.0716(5) 0.61244(12) 0.0407(10) Uani 1 1 d . . . . .
O2 O 0.5729(3) 0.6137(5) 0.72388(14) 0.0609(14) Uani 1 1 d . . . . .
O3 O 0.43251(17) 0.3846(5) 0.60009(12) 0.0387(9) Uani 1 1 d . . . . .
O4 O 0.51784(18) 0.5714(4) 0.61006(11) 0.0371(9) Uani 1 1 d . . . . .
N1 N 0.5556(2) 0.0626(5) 0.65676(13) 0.0312(10) Uani 1 1 d . . . . .
N2 N 0.5282(2) 0.3004(5) 0.63444(13) 0.0307(10) Uani 1 1 d . . . . .
C1 C 0.6004(3) 0.1688(6) 0.67369(15) 0.0326(12) Uani 1 1 d . . . . .
C2 C 0.5934(3) 0.3166(6) 0.64730(16) 0.0328(12) Uani 1 1 d . . . . .
H2 H 0.6195 0.3060 0.6244 0.039 Uiso 1 1 calc R . . . .
C3 C 0.6094(3) 0.4677(6) 0.66910(15) 0.0351(12) Uani 1 1 d . . . . .
H3A H 0.6534 0.4746 0.6714 0.042 Uiso 1 1 calc R . . . .
H3B H 0.5957 0.5558 0.6532 0.042 Uiso 1 1 calc R . . . .
C4 C 0.5836(3) 0.4851(7) 0.70916(17) 0.0418(14) Uani 1 1 d . . . . .
C5 C 0.5753(3) 0.3405(7) 0.73229(17) 0.0395(13) Uani 1 1 d . . . . .
H5 H 0.5641 0.3475 0.7585 0.047 Uiso 1 1 calc R . . . .
C6 C 0.5838(3) 0.1998(7) 0.71600(16) 0.0365(12) Uani 1 1 d . . . . .
H6 H 0.5791 0.1125 0.7321 0.044 Uiso 1 1 calc R . . . .
C7 C 0.6593(2) 0.0758(6) 0.66999(16) 0.0338(12) Uani 1 1 d . . . . .
H7A H 0.6883 0.1043 0.6906 0.041 Uiso 1 1 calc R . . . .
H7B H 0.6776 0.0932 0.6446 0.041 Uiso 1 1 calc R . . . .
C8 C 0.6384(3) -0.0974(6) 0.67443(18) 0.0391(13) Uani 1 1 d . . . . .
H8A H 0.6651 -0.1676 0.6603 0.047 Uiso 1 1 calc R . . . .
H8B H 0.6385 -0.1280 0.7019 0.047 Uiso 1 1 calc R . . . .
C9 C 0.5735(3) -0.1028(6) 0.65678(17) 0.0343(12) Uani 1 1 d . . . . .
H9A H 0.5733 -0.1454 0.6303 0.041 Uiso 1 1 calc R . . . .
H9B H 0.5467 -0.1653 0.6729 0.041 Uiso 1 1 calc R . . . .
C10 C 0.5152(3) 0.1328(6) 0.63248(16) 0.0328(12) Uani 1 1 d . . . . .
C11 C 0.5263(2) 0.3635(6) 0.55485(15) 0.0295(11) Uani 1 1 d . . . . .
C12 C 0.4999(3) 0.2406(6) 0.53374(16) 0.0322(12) Uani 1 1 d . . . . .
H12 H 0.4672 0.1850 0.5438 0.039 Uiso 1 1 calc R . . . .
C13 C 0.5231(3) 0.2024(6) 0.49721(17) 0.0367(13) Uani 1 1 d . . . . .
H13 H 0.5046 0.1226 0.4826 0.044 Uiso 1 1 calc R . . . .
C14 C 0.5732(3) 0.2793(6) 0.48172(17) 0.0345(12) Uani 1 1 d . . . . .
C15 C 0.5976(3) 0.4029(7) 0.50356(16) 0.0384(13) Uani 1 1 d . . . . .
H15 H 0.6302 0.4591 0.4936 0.046 Uiso 1 1 calc R . . . .
C16 C 0.5748(3) 0.4450(6) 0.53990(16) 0.0368(13) Uani 1 1 d . . . . .
H16 H 0.5921 0.5277 0.5540 0.044 Uiso 1 1 calc R . . . .
C17 C 0.5989(3) 0.2322(7) 0.44287(17) 0.0404(14) Uani 1 1 d . . . . .
H17A H 0.5762 0.1451 0.4323 0.061 Uiso 1 1 calc R . . . .
H17B H 0.5964 0.3194 0.4250 0.061 Uiso 1 1 calc R . . . .
H17C H 0.6408 0.2021 0.4465 0.061 Uiso 1 1 calc R . . . .
S2 S 0.74493(6) 0.64457(13) 0.59431(3) 0.0270(3) Uani 1 1 d . . . . .
O5 O 0.73042(18) 0.2916(4) 0.59790(11) 0.0353(9) Uani 1 1 d . . . . .
O6 O 0.7804(2) 0.8264(4) 0.71367(12) 0.0428(10) Uani 1 1 d . . . . .
O7 O 0.68169(16) 0.6091(4) 0.59206(10) 0.0319(8) Uani 1 1 d . . . . .
O8 O 0.76449(17) 0.7973(4) 0.60727(11) 0.0310(8) Uani 1 1 d . . . . .
N3 N 0.8013(2) 0.2805(4) 0.64818(13) 0.0275(9) Uani 1 1 d . . . . .
N4 N 0.7755(2) 0.5195(4) 0.62665(12) 0.0262(9) Uani 1 1 d . . . . .
C18 C 0.8392(2) 0.3897(5) 0.67138(14) 0.0272(11) Uani 1 1 d . . . . .
C19 C 0.8374(2) 0.5400(6) 0.64531(15) 0.0283(11) Uani 1 1 d . . . . .
H19 H 0.8687 0.5338 0.6252 0.034 Uiso 1 1 calc R . . . .
C20 C 0.8459(2) 0.6889(6) 0.66967(15) 0.0301(11) Uani 1 1 d . . . . .
H20A H 0.8870 0.6908 0.6806 0.036 Uiso 1 1 calc R . . . .
H20B H 0.8411 0.7798 0.6526 0.036 Uiso 1 1 calc R . . . .
C21 C 0.8014(3) 0.7009(6) 0.70274(15) 0.0325(12) Uani 1 1 d . . . . .
C22 C 0.7871(3) 0.5530(6) 0.72308(15) 0.0326(12) Uani 1 1 d . . . . .
H22 H 0.7637 0.5560 0.7456 0.039 Uiso 1 1 calc R . . . .
C23 C 0.8070(3) 0.4154(6) 0.71002(15) 0.0326(12) Uani 1 1 d . . . . .
H23 H 0.8006 0.3278 0.7258 0.039 Uiso 1 1 calc R . . . .
C24 C 0.8993(3) 0.3000(6) 0.67561(17) 0.0362(13) Uani 1 1 d . . . . .
H24A H 0.9206 0.3284 0.6998 0.043 Uiso 1 1 calc R . . . .
H24B H 0.9254 0.3209 0.6535 0.043 Uiso 1 1 calc R . . . .
C25 C 0.8794(3) 0.1274(6) 0.67627(17) 0.0372(13) Uani 1 1 d . . . . .
H25A H 0.8687 0.0957 0.7027 0.045 Uiso 1 1 calc R . . . .
H25B H 0.9117 0.0597 0.6671 0.045 Uiso 1 1 calc R . . . .
C26 C 0.8237(3) 0.1189(5) 0.64834(17) 0.0339(12) Uani 1 1 d . . . . .
H26A H 0.8352 0.0859 0.6222 0.041 Uiso 1 1 calc R . . . .
H26B H 0.7933 0.0469 0.6582 0.041 Uiso 1 1 calc R . . . .
C27 C 0.7655(2) 0.3518(5) 0.62178(14) 0.0272(11) Uani 1 1 d . . . . .
C28 C 0.7782(2) 0.6052(5) 0.54881(14) 0.0240(10) Uani 1 1 d . . . . .
C29 C 0.7549(2) 0.4881(5) 0.52487(15) 0.0300(11) Uani 1 1 d . . . . .
H29 H 0.7215 0.4297 0.5328 0.036 Uiso 1 1 calc R . . . .
C30 C 0.7813(3) 0.4573(6) 0.48890(15) 0.0310(12) Uani 1 1 d . . . . .
H30 H 0.7649 0.3793 0.4727 0.037 Uiso 1 1 calc R . . . .
C31 C 0.8317(2) 0.5414(6) 0.47678(15) 0.0300(11) Uani 1 1 d . . . . .
C32 C 0.8535(3) 0.6611(6) 0.50104(15) 0.0306(11) Uani 1 1 d . . . . .
H32 H 0.8863 0.7208 0.4928 0.037 Uiso 1 1 calc R . . . .
C33 C 0.8277(2) 0.6943(6) 0.53724(15) 0.0300(11) Uani 1 1 d . . . . .
H33 H 0.8433 0.7740 0.5532 0.036 Uiso 1 1 calc R . . . .
C34 C 0.8607(3) 0.5058(6) 0.43849(15) 0.0358(12) Uani 1 1 d . . . . .
H34A H 0.8647 0.3940 0.4356 0.054 Uiso 1 1 calc GR . . . .
H34B H 0.9002 0.5539 0.4379 0.054 Uiso 1 1 calc GR . . . .
H34C H 0.8358 0.5466 0.4174 0.054 Uiso 1 1 calc GR . . . .
O9 O 1.0000 0.360(3) 0.7500 0.038(5) Uiso 0.25 2 d S T P . .


_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
S1 O3 1.429(4) . ?
S1 O4 1.433(4) . ?
S1 N2 1.668(4) . ?
S1 C11 1.754(6) . ?
O1 C10 1.224(7) . ?
O2 C4 1.228(7) . ?
N1 C1 1.448(7) . ?
N1 C9 1.461(6) . ?
N1 C10 1.341(7) . ?
N2 C2 1.498(7) . ?
N2 C10 1.454(7) . ?
C1 C2 1.551(7) . ?
C1 C6 1.514(8) . ?
C1 C7 1.524(8) . ?
C2 H2 0.9800 . ?
C2 C3 1.521(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.493(8) . ?
C4 C5 1.472(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.333(8) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.551(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.540(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 C12 1.390(7) . ?
C11 C16 1.375(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.390(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.391(8) . ?
C14 C15 1.390(8) . ?
C14 C17 1.501(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.389(9) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
S2 O7 1.423(4) . ?
S2 O8 1.435(3) . ?
S2 N4 1.663(4) . ?
S2 C28 1.756(5) . ?
O5 C27 1.222(6) . ?
O6 C21 1.223(6) . ?
N3 C18 1.468(6) . ?
N3 C26 1.460(6) . ?
N3 C27 1.330(7) . ?
N4 C19 1.502(6) . ?
N4 C27 1.451(6) . ?
C18 C19 1.555(7) . ?
C18 C23 1.520(8) . ?
C18 C24 1.529(7) . ?
C19 H19 0.9800 . ?
C19 C20 1.523(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.508(8) . ?
C21 C22 1.472(7) . ?
C22 H22 0.9300 . ?
C22 C23 1.328(7) . ?
C23 H23 0.9300 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.531(7) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.539(8) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C28 C29 1.380(7) . ?
C28 C33 1.388(7) . ?
C29 H29 0.9300 . ?
C29 C30 1.388(8) . ?
C30 H30 0.9300 . ?
C30 C31 1.387(8) . ?
C31 C32 1.390(7) . ?
C31 C34 1.491(7) . ?
C32 H32 0.9300 . ?
C32 C33 1.393(8) . ?
C33 H33 0.9300 . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?

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
O3 S1 O4 119.8(2) . . ?
O3 S1 N2 106.9(2) . . ?
O3 S1 C11 109.2(2) . . ?
O4 S1 N2 104.6(2) . . ?
O4 S1 C11 108.2(3) . . ?
N2 S1 C11 107.4(2) . . ?
C1 N1 C9 114.7(4) . . ?
C10 N1 C1 113.9(4) . . ?
C10 N1 C9 127.2(4) . . ?
C2 N2 S1 122.4(4) . . ?
C10 N2 S1 118.1(3) . . ?
C10 N2 C2 106.8(4) . . ?
N1 C1 C2 102.4(4) . . ?
N1 C1 C6 108.3(5) . . ?
N1 C1 C7 102.5(4) . . ?
C6 C1 C2 112.7(5) . . ?
C6 C1 C7 112.8(4) . . ?
C7 C1 C2 116.7(5) . . ?
N2 C2 C1 100.3(4) . . ?
N2 C2 H2 109.3 . . ?
N2 C2 C3 115.6(5) . . ?
C1 C2 H2 109.3 . . ?
C3 C2 C1 112.5(4) . . ?
C3 C2 H2 109.3 . . ?
C2 C3 H3A 108.3 . . ?
C2 C3 H3B 108.3 . . ?
H3A C3 H3B 107.4 . . ?
C4 C3 C2 116.1(5) . . ?
C4 C3 H3A 108.3 . . ?
C4 C3 H3B 108.3 . . ?
O2 C4 C3 122.7(5) . . ?
O2 C4 C5 120.0(6) . . ?
C5 C4 C3 117.2(5) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.5(5) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 116.9 . . ?
C5 C6 C1 126.1(5) . . ?
C5 C6 H6 116.9 . . ?
C1 C7 H7A 111.1 . . ?
C1 C7 H7B 111.1 . . ?
C1 C7 C8 103.4(4) . . ?
H7A C7 H7B 109.0 . . ?
C8 C7 H7A 111.1 . . ?
C8 C7 H7B 111.1 . . ?
C7 C8 H8A 110.7 . . ?
C7 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
C9 C8 C7 105.3(4) . . ?
C9 C8 H8A 110.7 . . ?
C9 C8 H8B 110.7 . . ?
N1 C9 C8 102.7(4) . . ?
N1 C9 H9A 111.2 . . ?
N1 C9 H9B 111.2 . . ?
C8 C9 H9A 111.2 . . ?
C8 C9 H9B 111.2 . . ?
H9A C9 H9B 109.1 . . ?
O1 C10 N1 128.1(5) . . ?
O1 C10 N2 125.5(5) . . ?
N1 C10 N2 106.3(4) . . ?
C12 C11 S1 119.3(4) . . ?
C16 C11 S1 120.1(4) . . ?
C16 C11 C12 120.5(5) . . ?
C11 C12 H12 120.7 . . ?
C11 C12 C13 118.7(5) . . ?
C13 C12 H12 120.7 . . ?
C12 C13 H13 118.8 . . ?
C12 C13 C14 122.3(5) . . ?
C14 C13 H13 118.8 . . ?
C13 C14 C17 121.4(5) . . ?
C15 C14 C13 117.0(6) . . ?
C15 C14 C17 121.6(6) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 C14 121.9(6) . . ?
C16 C15 H15 119.1 . . ?
C11 C16 C15 119.6(5) . . ?
C11 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O7 S2 O8 119.7(2) . . ?
O7 S2 N4 106.4(2) . . ?
O7 S2 C28 109.5(2) . . ?
O8 S2 N4 105.1(2) . . ?
O8 S2 C28 108.4(2) . . ?
N4 S2 C28 106.9(2) . . ?
C26 N3 C18 114.0(4) . . ?
C27 N3 C18 113.4(4) . . ?
C27 N3 C26 128.8(4) . . ?
C19 N4 S2 123.9(3) . . ?
C27 N4 S2 119.6(3) . . ?
C27 N4 C19 107.2(4) . . ?
N3 C18 C19 101.8(4) . . ?
N3 C18 C23 106.7(4) . . ?
N3 C18 C24 102.5(4) . . ?
C23 C18 C19 111.5(4) . . ?
C23 C18 C24 113.9(4) . . ?
C24 C18 C19 118.4(5) . . ?
N4 C19 C18 99.2(4) . . ?
N4 C19 H19 110.0 . . ?
N4 C19 C20 115.4(4) . . ?
C18 C19 H19 110.0 . . ?
C20 C19 C18 111.8(4) . . ?
C20 C19 H19 110.0 . . ?
C19 C20 H20A 109.0 . . ?
C19 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C21 C20 C19 112.7(4) . . ?
C21 C20 H20A 109.0 . . ?
C21 C20 H20B 109.0 . . ?
O6 C21 C20 122.6(5) . . ?
O6 C21 C22 121.2(5) . . ?
C22 C21 C20 116.1(4) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 C21 121.5(5) . . ?
C23 C22 H22 119.3 . . ?
C18 C23 H23 117.4 . . ?
C22 C23 C18 125.2(5) . . ?
C22 C23 H23 117.4 . . ?
C18 C24 H24A 111.1 . . ?
C18 C24 H24B 111.1 . . ?
C18 C24 C25 103.5(4) . . ?
H24A C24 H24B 109.0 . . ?
C25 C24 H24A 111.1 . . ?
C25 C24 H24B 111.1 . . ?
C24 C25 H25A 110.7 . . ?
C24 C25 H25B 110.7 . . ?
C24 C25 C26 105.1(4) . . ?
H25A C25 H25B 108.8 . . ?
C26 C25 H25A 110.7 . . ?
C26 C25 H25B 110.7 . . ?
N3 C26 C25 102.8(4) . . ?
N3 C26 H26A 111.2 . . ?
N3 C26 H26B 111.2 . . ?
C25 C26 H26A 111.2 . . ?
C25 C26 H26B 111.2 . . ?
H26A C26 H26B 109.1 . . ?
O5 C27 N3 128.1(4) . . ?
O5 C27 N4 125.4(4) . . ?
N3 C27 N4 106.5(4) . . ?
C29 C28 S2 120.1(4) . . ?
C29 C28 C33 120.8(5) . . ?
C33 C28 S2 119.1(4) . . ?
C28 C29 H29 120.0 . . ?
C28 C29 C30 120.0(5) . . ?
C30 C29 H29 120.0 . . ?
C29 C30 H30 119.6 . . ?
C31 C30 C29 120.8(5) . . ?
C31 C30 H30 119.6 . . ?
C30 C31 C32 118.0(5) . . ?
C30 C31 C34 120.7(5) . . ?
C32 C31 C34 121.2(5) . . ?
C31 C32 H32 119.0 . . ?
C31 C32 C33 122.1(5) . . ?
C33 C32 H32 119.0 . . ?
C28 C33 C32 118.2(5) . . ?
C28 C33 H33 120.9 . . ?
C32 C33 H33 120.9 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?


_olex2_date_sample_data_collection 2019-02-25
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.270
_oxdiff_exptl_absorpt_empirical_full_min 0.700
