# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_jjshla
_database_code_depnum_ccdc_archive 'CCDC 1431894'
_audit_update_record             
;
2015-10-17 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;

_nottingham_internal_coll_name   JJSHLA
_nottingham_internal_coll_number 13051
_nottingham_internal_coll_client JJS/HWL
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '75 and 300S'
_nottingham_internal_coll_frame_width 1
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_date   22/11/2013
_nottingham_internal_coll_user   WL
_nottingham_internal_coll_location NOTTS
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_user WL
_nottingham_internal_process_date 25/11/2013
_nottingham_internal_solution_user WL
_nottingham_internal_solution_date 25/11/2013
_nottingham_internal_refinement_user WL
_nottingham_internal_refinement_date 25/11/2013
_nottingham_internal_validation_user WL
_nottingham_internal_validation_date 25/11/2013
_nottingham_internal_archive_date 25/11/2013

_audit_creation_date             2013-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4715)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H26 N2 O3'
_chemical_formula_sum            'C23 H26 N2 O3'
_chemical_formula_weight         378.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H26 N2 O3'
_chemical_oxdiff_usercomment     
'JJSHLA #13051 IN FOMBLIN FILM ON A MICROMOUNT FOR JJS/HWL'
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                   5.1957(2)
_cell_length_b                   24.5851(11)
_cell_length_c                   16.0276(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.625(4)
_cell_angle_gamma                90
_cell_volume                     2043.22(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3187
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.3430
_cell_measurement_theta_min      3.2820
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  1.267
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             808
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3, petroleum ether 40-60'
_exptl_crystal_size_max          0.3595
_exptl_crystal_size_mid          0.0313
_exptl_crystal_size_min          0.026
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_av_unetI/netI     0.0736
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7657
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.492
_diffrn_reflns_theta_min         3.296
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.3271
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'GV1000, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1838179000
_diffrn_orient_matrix_UB_12      0.0426871000
_diffrn_orient_matrix_UB_13      -0.0337312000
_diffrn_orient_matrix_UB_21      0.2092102000
_diffrn_orient_matrix_UB_22      -0.0439857000
_diffrn_orient_matrix_UB_23      -0.0063128000
_diffrn_orient_matrix_UB_31      -0.1038158000
_diffrn_orient_matrix_UB_32      -0.0129309000
_diffrn_orient_matrix_UB_33      -0.0899867000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2940
_reflns_number_total             4024
_reflns_odcompleteness_completeness 99.18
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL-2013 (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4024
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0749
_refine_ls_restrained_S_all      1.054
_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)+(0.1350P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1999
_refine_ls_wR_factor_ref         0.2229
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C22(H22), C23(H23), C24(H24),
 C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
N1 N 1.0695(4) 0.24467(8) 0.80936(13) 0.0283(5) Uani 1 1 d . . . . .
C2 C 1.2636(4) 0.27762(9) 0.83145(15) 0.0246(5) Uani 1 1 d . . . . .
C3 C 1.4171(5) 0.27070(10) 0.90740(17) 0.0316(6) Uani 1 1 d . . . . .
H3 H 1.5571 0.2946 0.9211 0.038 Uiso 1 1 calc R . . . .
C4 C 1.3621(6) 0.22968(11) 0.96009(18) 0.0383(6) Uani 1 1 d . . . . .
H4 H 1.4616 0.2251 1.0114 0.046 Uiso 1 1 calc R . . . .
C4A C 1.1566(6) 0.19385(10) 0.93839(18) 0.0373(6) Uani 1 1 d . . . . .
C5 C 1.0877(8) 0.15008(11) 0.9891(2) 0.0507(8) Uani 1 1 d . . . . .
H5 H 1.1816 0.1440 1.0410 0.061 Uiso 1 1 calc R . . . .
C6 C 0.8893(8) 0.11639(12) 0.9650(3) 0.0609(10) Uani 1 1 d . . . . .
H6 H 0.8434 0.0873 1.0002 0.073 Uiso 1 1 calc R . . . .
C7 C 0.7522(7) 0.12497(11) 0.8874(3) 0.0591(10) Uani 1 1 d . . . . .
H7 H 0.6155 0.1010 0.8703 0.071 Uiso 1 1 calc R . . . .
C8A C 1.0164(5) 0.20270(9) 0.86051(18) 0.0324(6) Uani 1 1 d . . . . .
C8 C 0.8112(6) 0.16674(11) 0.8365(2) 0.0466(8) Uani 1 1 d . . . . .
H8 H 0.7149 0.1719 0.7848 0.056 Uiso 1 1 calc R . . . .
C9 C 1.3116(4) 0.32487(8) 0.77442(15) 0.0252(5) Uani 1 1 d . . . . .
H9 H 1.4950 0.3366 0.7853 0.030 Uiso 1 1 calc R . . . .
C10 C 1.2727(6) 0.30868(10) 0.68249(17) 0.0365(6) Uani 1 1 d . . . . .
H10A H 1.3308 0.3389 0.6474 0.044 Uiso 1 1 calc R . . . .
H10B H 1.3812 0.2766 0.6722 0.044 Uiso 1 1 calc R . . . .
O11 O 1.0119(4) 0.29622(8) 0.65820(13) 0.0460(6) Uani 1 1 d . . . . .
H11 H 0.962(8) 0.272(2) 0.698(3) 0.069 Uiso 1 1 d R . . . .
C12 C 1.1354(4) 0.37339(8) 0.79522(15) 0.0237(5) Uani 1 1 d . . . . .
H12 H 0.9525 0.3609 0.7867 0.028 Uiso 1 1 calc R . . . .
N13 N 1.1811(3) 0.38813(7) 0.88322(13) 0.0225(4) Uani 1 1 d . . . . .
H13 H 1.338(6) 0.3925(12) 0.9018(19) 0.027 Uiso 1 1 d R . . . .
C14 C 0.9870(4) 0.39340(8) 0.93405(15) 0.0211(5) Uani 1 1 d . . . . .
O15 O 0.7586(3) 0.38849(7) 0.91262(11) 0.0277(4) Uani 1 1 d . . . . .
O16 O 1.0831(3) 0.40539(7) 1.01241(11) 0.0269(4) Uani 1 1 d . . . . .
C17 C 0.9099(4) 0.41240(10) 1.08126(16) 0.0282(5) Uani 1 1 d . . . . .
C18 C 0.7836(6) 0.35851(12) 1.0998(2) 0.0431(7) Uani 1 1 d . . . . .
H18A H 0.6514 0.3501 1.0554 0.065 Uiso 1 1 calc GR . . . .
H18B H 0.7035 0.3609 1.1535 0.065 Uiso 1 1 calc GR . . . .
H18C H 0.9142 0.3297 1.1027 0.065 Uiso 1 1 calc GR . . . .
C19 C 1.0964(5) 0.43026(15) 1.15309(18) 0.0437(7) Uani 1 1 d . . . . .
H19A H 1.2259 0.4018 1.1646 0.066 Uiso 1 1 calc GR . . . .
H19B H 1.0012 0.4364 1.2031 0.066 Uiso 1 1 calc GR . . . .
H19C H 1.1821 0.4640 1.1378 0.066 Uiso 1 1 calc GR . . . .
C20 C 0.7164(5) 0.45780(10) 1.06167(18) 0.0338(6) Uani 1 1 d . . . . .
H20A H 0.8045 0.4889 1.0379 0.051 Uiso 1 1 calc GR . . . .
H20B H 0.6391 0.4690 1.1132 0.051 Uiso 1 1 calc GR . . . .
H20C H 0.5809 0.4447 1.0213 0.051 Uiso 1 1 calc GR . . . .
C21 C 1.1691(4) 0.42152(9) 0.73778(15) 0.0238(5) Uani 1 1 d . . . . .
C22 C 1.3833(4) 0.45583(9) 0.74746(16) 0.0277(5) Uani 1 1 d . . . . .
H22 H 1.5114 0.4492 0.7912 0.033 Uiso 1 1 calc R . . . .
C23 C 1.4109(5) 0.49936(9) 0.69403(17) 0.0318(6) Uani 1 1 d . . . . .
H23 H 1.5551 0.5229 0.7024 0.038 Uiso 1 1 calc R . . . .
C24 C 1.2288(5) 0.50888(9) 0.62804(17) 0.0330(6) Uani 1 1 d . . . . .
H24 H 1.2495 0.5384 0.5908 0.040 Uiso 1 1 calc R . . . .
C25 C 1.0168(5) 0.47463(10) 0.61753(17) 0.0339(6) Uani 1 1 d . . . . .
H25 H 0.8908 0.4809 0.5730 0.041 Uiso 1 1 calc R . . . .
C26 C 0.9877(4) 0.43146(9) 0.67140(16) 0.0284(5) Uani 1 1 d . . . . .
H26 H 0.8423 0.4082 0.6632 0.034 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
N1 C2 1.324(3) . ?
N1 C8A 1.357(3) . ?
C2 C3 1.423(3) . ?
C2 C9 1.509(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.357(4) . ?
C4 H4 0.9500 . ?
C4 C4A 1.411(4) . ?
C4A C5 1.408(4) . ?
C4A C8A 1.422(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.359(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.410(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.358(5) . ?
C8A C8 1.419(4) . ?
C8 H8 0.9500 . ?
C9 H9 1.0000 . ?
C9 C10 1.527(4) . ?
C9 C12 1.553(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 O11 1.419(4) . ?
O11 H11 0.93(5) . ?
C12 H12 1.0000 . ?
C12 N13 1.461(3) . ?
C12 C21 1.516(3) . ?
N13 H13 0.86(3) . ?
N13 C14 1.342(3) . ?
C14 O15 1.220(3) . ?
C14 O16 1.354(3) . ?
O16 C17 1.477(3) . ?
C17 C18 1.516(4) . ?
C17 C19 1.522(3) . ?
C17 C20 1.521(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.397(3) . ?
C21 C26 1.398(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.384(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.394(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.388(4) . ?
C25 H25 0.9500 . ?
C25 C26 1.382(4) . ?
C26 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C8A 118.9(2) . . ?
N1 C2 C3 122.1(2) . . ?
N1 C2 C9 117.48(19) . . ?
C3 C2 C9 120.3(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C4A 119.8(2) . . ?
C4A C4 H4 120.1 . . ?
C4 C4A C8A 117.3(2) . . ?
C5 C4A C4 123.4(3) . . ?
C5 C4A C8A 119.2(3) . . ?
C4A C5 H5 119.4 . . ?
C6 C5 C4A 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 120.3 . . ?
C5 C6 C7 119.4(3) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.5(3) . . ?
C8 C7 H7 119.3 . . ?
N1 C8A C4A 122.3(2) . . ?
N1 C8A C8 119.2(3) . . ?
C8 C8A C4A 118.5(3) . . ?
C7 C8 C8A 120.2(3) . . ?
C7 C8 H8 119.9 . . ?
C8A C8 H8 119.9 . . ?
C2 C9 H9 108.0 . . ?
C2 C9 C10 111.53(18) . . ?
C2 C9 C12 109.8(2) . . ?
C10 C9 H9 108.0 . . ?
C10 C9 C12 111.30(19) . . ?
C12 C9 H9 108.0 . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
O11 C10 C9 112.8(2) . . ?
O11 C10 H10A 109.0 . . ?
O11 C10 H10B 109.0 . . ?
C10 O11 H11 105(3) . . ?
C9 C12 H12 107.6 . . ?
N13 C12 C9 109.61(17) . . ?
N13 C12 H12 107.6 . . ?
N13 C12 C21 112.00(17) . . ?
C21 C12 C9 112.1(2) . . ?
C21 C12 H12 107.6 . . ?
C12 N13 H13 117(2) . . ?
C14 N13 C12 121.82(17) . . ?
C14 N13 H13 121(2) . . ?
N13 C14 O16 109.68(17) . . ?
O15 C14 N13 125.0(2) . . ?
O15 C14 O16 125.3(2) . . ?
C14 O16 C17 120.78(16) . . ?
O16 C17 C18 109.7(2) . . ?
O16 C17 C19 102.11(19) . . ?
O16 C17 C20 110.9(2) . . ?
C18 C17 C19 111.5(2) . . ?
C18 C17 C20 113.1(2) . . ?
C20 C17 C19 109.0(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C12 121.70(19) . . ?
C22 C21 C26 118.2(2) . . ?
C26 C21 C12 120.0(2) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.7(2) . . ?
C23 C22 H22 119.6 . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C24 120.5(2) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 120.5 . . ?
C25 C24 C23 119.1(2) . . ?
C25 C24 H24 120.5 . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.5(2) . . ?
C26 C25 H25 119.8 . . ?
C21 C26 H26 119.5 . . ?
C25 C26 C21 121.0(2) . . ?
C25 C26 H26 119.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O11 H11 N1 0.93(5) 1.95(5) 2.734(3) 141(4) .
N13 H13 O15 0.86(3) 2.18(3) 3.008(2) 161(3) 1_655

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 -1.1(4) . . . . ?
N1 C2 C9 C10 -39.3(3) . . . . ?
N1 C2 C9 C12 84.6(3) . . . . ?
N1 C8A C8 C7 -179.0(3) . . . . ?
C2 N1 C8A C4A 2.1(4) . . . . ?
C2 N1 C8A C8 -179.0(2) . . . . ?
C2 C3 C4 C4A 1.1(4) . . . . ?
C2 C9 C10 O11 67.1(3) . . . . ?
C2 C9 C12 N13 56.8(2) . . . . ?
C2 C9 C12 C21 -178.11(17) . . . . ?
C3 C2 C9 C10 143.1(2) . . . . ?
C3 C2 C9 C12 -93.1(3) . . . . ?
C3 C4 C4A C5 179.5(3) . . . . ?
C3 C4 C4A C8A 0.4(4) . . . . ?
C4 C4A C5 C6 -179.4(3) . . . . ?
C4 C4A C8A N1 -2.0(4) . . . . ?
C4 C4A C8A C8 179.1(3) . . . . ?
C4A C5 C6 C7 0.9(5) . . . . ?
C4A C8A C8 C7 0.0(4) . . . . ?
C5 C4A C8A N1 178.8(3) . . . . ?
C5 C4A C8A C8 -0.1(4) . . . . ?
C5 C6 C7 C8 -1.1(5) . . . . ?
C6 C7 C8 C8A 0.7(5) . . . . ?
C8A N1 C2 C3 -0.5(4) . . . . ?
C8A N1 C2 C9 -178.1(2) . . . . ?
C8A C4A C5 C6 -0.3(4) . . . . ?
C9 C2 C3 C4 176.4(2) . . . . ?
C9 C12 N13 C14 -129.0(2) . . . . ?
C9 C12 C21 C22 -76.3(3) . . . . ?
C9 C12 C21 C26 101.6(2) . . . . ?
C10 C9 C12 N13 -179.15(19) . . . . ?
C10 C9 C12 C21 -54.1(2) . . . . ?
C12 C9 C10 O11 -55.9(3) . . . . ?
C12 N13 C14 O15 -2.6(3) . . . . ?
C12 N13 C14 O16 177.92(17) . . . . ?
C12 C21 C22 C23 179.6(2) . . . . ?
C12 C21 C26 C25 -179.0(2) . . . . ?
N13 C12 C21 C22 47.4(3) . . . . ?
N13 C12 C21 C26 -134.7(2) . . . . ?
N13 C14 O16 C17 -178.91(18) . . . . ?
C14 O16 C17 C18 66.8(3) . . . . ?
C14 O16 C17 C19 -174.9(2) . . . . ?
C14 O16 C17 C20 -58.9(3) . . . . ?
O15 C14 O16 C17 1.6(3) . . . . ?
C21 C12 N13 C14 105.9(2) . . . . ?
C21 C22 C23 C24 -1.8(4) . . . . ?
C22 C21 C26 C25 -1.1(4) . . . . ?
C22 C23 C24 C25 1.1(4) . . . . ?
C23 C24 C25 C26 -0.5(4) . . . . ?
C24 C25 C26 C21 0.5(4) . . . . ?
C26 C21 C22 C23 1.8(4) . . . . ?

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
0 0 -1 0.0287 0.0004 -0.0022 -1.0003 0.0337 0.0065 0.0900
0 0 1 0.0027 -0.0004 0.0022 1.0003 -0.0337 -0.0065 -0.0900
2 1 -2 0.1680 2.0027 1.0031 -2.0039 0.4785 0.3875 -0.0406
-2 -1 2 0.1680 -2.0027 -1.0031 2.0039 -0.4785 -0.3875 0.0406
0 -1 0 0.0180 -0.0003 -0.9995 -0.0009 -0.0427 0.0439 0.0130
0 1 0 0.0080 0.0003 0.9995 0.0009 0.0427 -0.0439 -0.0130
-1 2 10 0.0273 -1.0040 2.0171 10.0065 -0.4360 -0.3619 -0.8223


####################################################################### 
# 
# 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_jjshlb
_database_code_depnum_ccdc_archive 'CCDC 1431895'
_audit_update_record             
;
2015-10-17 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;
_nottingham_internal_coll_name   JJSHLB
_nottingham_internal_coll_number 13517
_nottingham_internal_coll_client JJS/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time '15.0000, 60.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   14/04/2014
_nottingham_internal_coll_location NOTTS
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date 15/04/2014
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 9/5/2014
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 9/5/2014
_nottingham_internal_refinement_user pczwl
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 22/5/2014
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 22/5/2014
_refine_special_details          
;
 ?
;
_audit_creation_date             2014-05-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H24 N2 O3 S'
_chemical_formula_sum            'C21 H24 N2 O3 S'
_chemical_formula_weight         384.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H24 N2 O3 S'
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           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                   5.28349(11)
_cell_length_b                   9.9736(2)
_cell_length_c                   36.4673(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.3374(19)
_cell_angle_gamma                90
_cell_volume                     1920.06(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6744
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.3210
_cell_measurement_theta_min      4.5830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.694
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.764
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.3174
_exptl_crystal_size_mid          0.0521
_exptl_crystal_size_min          0.0431
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            13248
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.542
_diffrn_reflns_theta_min         2.425
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.6296
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'GV1000, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0948295000
_diffrn_orient_matrix_UB_12      -0.1450822000
_diffrn_orient_matrix_UB_13      -0.0052356000
_diffrn_orient_matrix_UB_21      -0.0443165000
_diffrn_orient_matrix_UB_22      0.0257485000
_diffrn_orient_matrix_UB_23      -0.0414295000
_diffrn_orient_matrix_UB_31      0.2722796000
_diffrn_orient_matrix_UB_32      -0.0463769000
_diffrn_orient_matrix_UB_33      -0.0067078000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3468
_reflns_number_total             3838
_reflns_odcompleteness_completeness 99.84
_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, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3838
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0412
_refine_ls_restrained_S_all      1.027
_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)+(0.0569P)²+1.1476P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1088
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C21(H21), C22(H22), C23(H23), C24(H24),
 C25(H25)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 1.14298(8) 0.73006(4) 0.65670(2) 0.02861(13) Uani 1 1 d . . . . .
C2 C 0.9362(3) 0.85894(16) 0.66779(4) 0.0197(3) Uani 1 1 d . . . . .
N3 N 0.7644(3) 0.82744(15) 0.69067(4) 0.0234(3) Uani 1 1 d . . . . .
C3A C 0.7854(3) 0.69384(17) 0.70120(4) 0.0225(3) Uani 1 1 d . . . . .
C4 C 0.6276(4) 0.62744(19) 0.72510(5) 0.0287(4) Uani 1 1 d . . . . .
H4 H 0.4907 0.6732 0.7357 0.034 Uiso 1 1 calc R . . . .
C5 C 0.6741(4) 0.49433(19) 0.73305(5) 0.0306(4) Uani 1 1 d . . . . .
H5 H 0.5667 0.4482 0.7491 0.037 Uiso 1 1 calc R . . . .
C6 C 0.8748(4) 0.42638(19) 0.71810(5) 0.0319(4) Uani 1 1 d . . . . .
H6 H 0.9045 0.3352 0.7244 0.038 Uiso 1 1 calc R . . . .
C7 C 1.0323(4) 0.48974(19) 0.69411(5) 0.0332(4) Uani 1 1 d . . . . .
H7 H 1.1692 0.4432 0.6838 0.040 Uiso 1 1 calc R . . . .
C7A C 0.9843(3) 0.62347(18) 0.68558(4) 0.0252(4) Uani 1 1 d . . . . .
C8 C 0.9657(3) 0.99835(16) 0.65285(4) 0.0181(3) Uani 1 1 d . . . . .
H8 H 1.1265 1.0015 0.6393 0.022 Uiso 1 1 calc R . . . .
C9 C 0.9884(3) 1.09848(17) 0.68470(4) 0.0246(3) Uani 1 1 d . . . . .
H9A H 1.1319 1.0718 0.7014 0.030 Uiso 1 1 calc R . . . .
H9B H 1.0262 1.1885 0.6749 0.030 Uiso 1 1 calc R . . . .
O10 O 0.7643(3) 1.10572(14) 0.70493(3) 0.0328(3) Uani 1 1 d . . . . .
H10 H 0.729(5) 1.029(3) 0.7098(7) 0.049 Uiso 1 1 d R . . . .
C11 C 0.7442(3) 1.03392(16) 0.62551(4) 0.0181(3) Uani 1 1 d . . . . .
H11 H 0.5816 1.0196 0.6380 0.022 Uiso 1 1 calc R . . . .
N12 N 0.7511(2) 0.94179(14) 0.59437(3) 0.0189(3) Uani 1 1 d . . . . .
H12 H 0.894(4) 0.921(2) 0.5863(5) 0.023 Uiso 1 1 d R . . . .
C13 C 0.5378(3) 0.90232(15) 0.57586(4) 0.0170(3) Uani 1 1 d . . . . .
O14 O 0.3236(2) 0.92907(12) 0.58459(3) 0.0232(3) Uani 1 1 d . . . . .
O15 O 0.59860(19) 0.82794(11) 0.54649(3) 0.0191(2) Uani 1 1 d . . . . .
C16 C 0.3997(3) 0.76620(16) 0.52243(4) 0.0197(3) Uani 1 1 d . . . . .
C17 C 0.2602(3) 0.66070(18) 0.54400(5) 0.0291(4) Uani 1 1 d . . . . .
H17A H 0.3828 0.5977 0.5552 0.044 Uiso 1 1 calc GR . . . .
H17B H 0.1421 0.6120 0.5274 0.044 Uiso 1 1 calc GR . . . .
H17C H 0.1658 0.7045 0.5632 0.044 Uiso 1 1 calc GR . . . .
C18 C 0.5535(3) 0.7024(2) 0.49277(5) 0.0353(5) Uani 1 1 d . . . . .
H18A H 0.6447 0.7723 0.4798 0.053 Uiso 1 1 calc GR . . . .
H18B H 0.4397 0.6547 0.4753 0.053 Uiso 1 1 calc GR . . . .
H18C H 0.6753 0.6390 0.5040 0.053 Uiso 1 1 calc GR . . . .
C19 C 0.2203(3) 0.87085(18) 0.50579(4) 0.0241(3) Uani 1 1 d . . . . .
H19A H 0.1182 0.9090 0.5250 0.036 Uiso 1 1 calc GR . . . .
H19B H 0.1085 0.8288 0.4870 0.036 Uiso 1 1 calc GR . . . .
H19C H 0.3185 0.9422 0.4946 0.036 Uiso 1 1 calc GR . . . .
C20 C 0.7572(3) 1.18008(17) 0.61390(4) 0.0193(3) Uani 1 1 d . . . . .
C21 C 0.9500(3) 1.22529(18) 0.59202(4) 0.0230(3) Uani 1 1 d . . . . .
H21 H 1.0686 1.1632 0.5830 0.028 Uiso 1 1 calc R . . . .
C22 C 0.9700(3) 1.36008(18) 0.58339(5) 0.0263(4) Uani 1 1 d . . . . .
H22 H 1.1018 1.3896 0.5684 0.032 Uiso 1 1 calc R . . . .
C23 C 0.7992(3) 1.45219(18) 0.59649(5) 0.0272(4) Uani 1 1 d . . . . .
H23 H 0.8139 1.5446 0.5906 0.033 Uiso 1 1 calc R . . . .
C24 C 0.6065(3) 1.40804(19) 0.61827(5) 0.0299(4) Uani 1 1 d . . . . .
H24 H 0.4882 1.4704 0.6273 0.036 Uiso 1 1 calc R . . . .
C25 C 0.5863(3) 1.27317(18) 0.62687(5) 0.0254(4) Uani 1 1 d . . . . .
H25 H 0.4540 1.2439 0.6418 0.030 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
S1 C2 1.7452(16) . ?
S1 C7A 1.7361(18) . ?
C2 N3 1.296(2) . ?
C2 C8 1.504(2) . ?
N3 C3A 1.390(2) . ?
C3A C4 1.397(2) . ?
C3A C7A 1.404(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.384(3) . ?
C7 H7 0.9500 . ?
C7 C7A 1.391(3) . ?
C8 H8 1.0000 . ?
C8 C9 1.533(2) . ?
C8 C11 1.547(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 O10 1.422(2) . ?
O10 H10 0.81(3) . ?
C11 H11 1.0000 . ?
C11 N12 1.4624(19) . ?
C11 C20 1.520(2) . ?
N12 H12 0.85(2) . ?
N12 C13 1.348(2) . ?
C13 O14 1.2179(19) . ?
C13 O15 1.3523(18) . ?
O15 C16 1.4758(18) . ?
C16 C17 1.522(2) . ?
C16 C18 1.519(2) . ?
C16 C19 1.520(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.394(2) . ?
C20 C25 1.391(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.386(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.386(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.389(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.386(3) . ?
C25 H25 0.9500 . ?

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
C7A S1 C2 89.32(8) . . ?
N3 C2 S1 115.60(13) . . ?
N3 C2 C8 122.88(15) . . ?
C8 C2 S1 121.47(12) . . ?
C2 N3 C3A 111.11(14) . . ?
N3 C3A C4 125.71(16) . . ?
N3 C3A C7A 114.82(15) . . ?
C4 C3A C7A 119.46(16) . . ?
C3A C4 H4 120.6 . . ?
C5 C4 C3A 118.80(17) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.31(17) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 120.91(18) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 121.0 . . ?
C6 C7 C7A 118.06(18) . . ?
C7A C7 H7 121.0 . . ?
C3A C7A S1 109.15(13) . . ?
C7 C7A S1 129.41(15) . . ?
C7 C7A C3A 121.43(17) . . ?
C2 C8 H8 108.1 . . ?
C2 C8 C9 109.51(12) . . ?
C2 C8 C11 111.03(13) . . ?
C9 C8 H8 108.1 . . ?
C9 C8 C11 111.88(13) . . ?
C11 C8 H8 108.1 . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
O10 C9 C8 112.64(14) . . ?
O10 C9 H9A 109.1 . . ?
O10 C9 H9B 109.1 . . ?
C9 O10 H10 105.7(19) . . ?
C8 C11 H11 108.3 . . ?
N12 C11 C8 108.32(12) . . ?
N12 C11 H11 108.3 . . ?
N12 C11 C20 112.54(12) . . ?
C20 C11 C8 110.97(12) . . ?
C20 C11 H11 108.3 . . ?
C11 N12 H12 118.3(14) . . ?
C13 N12 C11 121.71(13) . . ?
C13 N12 H12 119.5(14) . . ?
N12 C13 O15 109.64(13) . . ?
O14 C13 N12 124.87(14) . . ?
O14 C13 O15 125.49(14) . . ?
C13 O15 C16 120.89(12) . . ?
O15 C16 C17 109.23(13) . . ?
O15 C16 C18 102.09(12) . . ?
O15 C16 C19 111.61(13) . . ?
C18 C16 C17 111.27(15) . . ?
C18 C16 C19 110.27(15) . . ?
C19 C16 C17 111.95(14) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C11 120.80(14) . . ?
C25 C20 C11 120.52(15) . . ?
C25 C20 C21 118.56(16) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.54(16) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 119.7 . . ?
C21 C22 C23 120.53(16) . . ?
C23 C22 H22 119.7 . . ?
C22 C23 H23 120.3 . . ?
C22 C23 C24 119.33(17) . . ?
C24 C23 H23 120.3 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.13(17) . . ?
C25 C24 H24 119.9 . . ?
C20 C25 H25 119.5 . . ?
C24 C25 C20 120.91(17) . . ?
C24 C25 H25 119.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O10 H10 N3 0.81(3) 2.14(3) 2.824(2) 142(3) .
N12 H12 O14 0.85(2) 2.28(2) 3.0627(17) 154.9(18) 1_655

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
S1 C2 N3 C3A -0.27(18) . . . . ?
S1 C2 C8 C9 -124.10(13) . . . . ?
S1 C2 C8 C11 111.86(13) . . . . ?
C2 S1 C7A C3A 0.42(13) . . . . ?
C2 S1 C7A C7 -178.83(18) . . . . ?
C2 N3 C3A C4 -178.98(16) . . . . ?
C2 N3 C3A C7A 0.6(2) . . . . ?
C2 C8 C9 O10 -64.82(18) . . . . ?
C2 C8 C11 N12 -62.72(16) . . . . ?
C2 C8 C11 C20 173.28(12) . . . . ?
N3 C2 C8 C9 53.1(2) . . . . ?
N3 C2 C8 C11 -70.98(19) . . . . ?
N3 C3A C4 C5 -179.62(16) . . . . ?
N3 C3A C7A S1 -0.67(18) . . . . ?
N3 C3A C7A C7 178.65(16) . . . . ?
C3A C4 C5 C6 0.6(3) . . . . ?
C4 C3A C7A S1 178.95(13) . . . . ?
C4 C3A C7A C7 -1.7(3) . . . . ?
C4 C5 C6 C7 -1.2(3) . . . . ?
C5 C6 C7 C7A 0.3(3) . . . . ?
C6 C7 C7A S1 -179.67(15) . . . . ?
C6 C7 C7A C3A 1.2(3) . . . . ?
C7A S1 C2 N3 -0.10(13) . . . . ?
C7A S1 C2 C8 177.26(13) . . . . ?
C7A C3A C4 C5 0.8(3) . . . . ?
C8 C2 N3 C3A -177.58(14) . . . . ?
C8 C11 N12 C13 148.01(14) . . . . ?
C8 C11 C20 C21 68.72(18) . . . . ?
C8 C11 C20 C25 -107.09(16) . . . . ?
C9 C8 C11 N12 174.60(13) . . . . ?
C9 C8 C11 C20 50.60(17) . . . . ?
C11 C8 C9 O10 58.72(18) . . . . ?
C11 N12 C13 O14 -6.3(2) . . . . ?
C11 N12 C13 O15 174.30(13) . . . . ?
C11 C20 C21 C22 -176.01(14) . . . . ?
C11 C20 C25 C24 175.94(15) . . . . ?
N12 C11 C20 C21 -52.84(19) . . . . ?
N12 C11 C20 C25 131.34(15) . . . . ?
N12 C13 O15 C16 176.96(13) . . . . ?
C13 O15 C16 C17 -65.60(18) . . . . ?
C13 O15 C16 C18 176.51(14) . . . . ?
C13 O15 C16 C19 58.74(18) . . . . ?
O14 C13 O15 C16 -2.5(2) . . . . ?
C20 C11 N12 C13 -88.93(17) . . . . ?
C20 C21 C22 C23 0.3(2) . . . . ?
C21 C20 C25 C24 0.0(2) . . . . ?
C21 C22 C23 C24 -0.3(3) . . . . ?
C22 C23 C24 C25 0.2(3) . . . . ?
C23 C24 C25 C20 -0.1(3) . . . . ?
C25 C20 C21 C22 -0.1(2) . . . . ?

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
0 5 4 0.0290 0.0021 5.0042 3.9852 -0.7471 -0.0363 -0.2583
0 -5 -4 0.0140 -0.0021 -5.0042 -3.9852 0.7471 0.0363 0.2583
0 0 -1 0.0248 0.0001 -0.0002 -1.0004 0.0053 0.0414 0.0067
0 0 1 0.0248 -0.0001 0.0002 1.0004 -0.0053 -0.0414 -0.0067
3 -2 2 0.1358 2.9962 -1.9913 1.9868 -0.0056 -0.2664 0.8948
-2 -5 -3 0.0752 -2.0005 -5.0105 -2.9712 0.9322 0.0827 -0.2924
3 3 0 0.1358 2.9989 3.0118 -0.0303 -0.7212 -0.0541 0.6771
0 5 -15 0.0264 0.0041 5.0007 -15.0218 -0.6473 0.7509 -0.1300
0 -5 15 0.0181 -0.0041 -5.0007 15.0218 0.6473 -0.7509 0.1300
0 -4 -18 0.0177 -0.0001 -4.0061 -17.9935 0.6754 0.6423 0.3065

_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: i-PrOH'
