# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_engle207
_database_code_depnum_ccdc_archive 'CCDC 2144251'
loop_
_audit_author_name
_audit_author_address
'Milan Gembicky'
;University of California San Diego
United States of America
;
_audit_update_record             
;
2022-01-25 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;
_audit_creation_date             2019-09-06
_audit_creation_method           
;
Olex2 1.2-beta
(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         'C14 H16 N4 O4 W'
_chemical_formula_sum            'C14 H16 N4 O4 W'
_chemical_formula_weight         488.16
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
W W -0.8490 6.8722 '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                   8.6484(7)
_cell_length_b                   14.2399(12)
_cell_length_c                   13.3208(15)
_cell_angle_alpha                90
_cell_angle_beta                 97.4980(10)
_cell_angle_gamma                90
_cell_volume                     1626.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7283
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.71
_cell_measurement_theta_min      2.77
_shelx_estimated_absorpt_T_max   0.536
_shelx_estimated_absorpt_T_min   0.458
_exptl_absorpt_coefficient_mu    7.127
_exptl_absorpt_correction_T_max  0.4910
_exptl_absorpt_correction_T_min  0.3858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0855 before and 0.0709 after correction.
The Ratio of minimum to maximum transmission is 0.7857.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.994
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8406
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.773
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 8.258
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1639
_reflns_number_total             1671
_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       'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker, 2017)'
_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         0.516
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.117
_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     107
_refine_ls_number_reflns         1671
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0187
_refine_ls_R_factor_gt           0.0183
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0077P)²+1.6956P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0450
_refine_ls_wR_factor_ref         0.0452
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C)
;
_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
W1 W 0.5000 0.65253(2) 0.2500 0.01155(7) Uani 1 2 d S T P . .
O2 O 0.3993(3) 0.48794(14) 0.09802(16) 0.0216(4) Uani 1 1 d . . . . .
O4 O 0.1614(3) 0.62633(17) 0.3127(2) 0.0313(5) Uani 1 1 d . . . . .
N3 N 0.6516(4) 0.85101(14) 0.3454(2) 0.0186(6) Uani 1 1 d . . . . .
N4 N 0.5420(3) 0.77858(15) 0.45756(18) 0.0162(5) Uani 1 1 d . . . . .
C1 C 0.4348(3) 0.55140(19) 0.1512(2) 0.0160(6) Uani 1 1 d . . . . .
C2 C 0.2833(4) 0.64141(18) 0.2910(3) 0.0181(7) Uani 1 1 d . . . . .
C3 C 0.5747(3) 0.76988(19) 0.3608(2) 0.0151(6) Uani 1 1 d . . . . .
C4 C 0.5952(4) 0.8633(2) 0.5004(3) 0.0232(7) Uani 1 1 d . . . . .
H4 H 0.5847 0.8851 0.5666 0.028 Uiso 1 1 calc R . . . .
C5 C 0.6644(4) 0.9085(2) 0.4300(2) 0.0234(7) Uani 1 1 d . . . . .
H5 H 0.7129 0.9684 0.4368 0.028 Uiso 1 1 calc R . . . .
C6 C 0.4680(4) 0.7078(2) 0.5140(2) 0.0212(6) Uani 1 1 d . . . . .
H6A H 0.3589 0.7002 0.4843 0.032 Uiso 1 1 calc GR . . . .
H6B H 0.4721 0.7277 0.5847 0.032 Uiso 1 1 calc GR . . . .
H6C H 0.5230 0.6479 0.5110 0.032 Uiso 1 1 calc GR . . . .
C7 C 0.7178(4) 0.8783(2) 0.2546(2) 0.0255(7) Uani 1 1 d . . . . .
H7A H 0.7302 0.8225 0.2134 0.038 Uiso 1 1 calc GR . . . .
H7B H 0.8198 0.9077 0.2740 0.038 Uiso 1 1 calc GR . . . .
H7C H 0.6480 0.9230 0.2155 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
W1 C1 1.982(3) . ?
W1 C1 1.982(3) 2_655 ?
W1 C2 2.026(4) 2_655 ?
W1 C2 2.026(4) . ?
W1 C3 2.267(3) . ?
W1 C3 2.267(3) 2_655 ?
O2 C1 1.165(4) . ?
O4 C2 1.149(4) . ?
N3 C3 1.362(4) . ?
N3 C5 1.385(4) . ?
N3 C7 1.457(4) . ?
N4 C3 1.361(4) . ?
N4 C4 1.387(4) . ?
N4 C6 1.455(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.341(5) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 W1 C1 86.81(16) . 2_655 ?
C1 W1 C2 87.54(12) 2_655 . ?
C1 W1 C2 85.95(12) . . ?
C1 W1 C2 85.95(12) 2_655 2_655 ?
C1 W1 C2 87.54(12) . 2_655 ?
C1 W1 C3 179.05(9) . . ?
C1 W1 C3 94.09(12) . 2_655 ?
C1 W1 C3 94.09(12) 2_655 . ?
C1 W1 C3 179.05(9) 2_655 2_655 ?
C2 W1 C2 171.04(15) 2_655 . ?
C2 W1 C3 92.19(11) 2_655 . ?
C2 W1 C3 94.42(11) 2_655 2_655 ?
C2 W1 C3 94.42(11) . . ?
C2 W1 C3 92.19(11) . 2_655 ?
C3 W1 C3 85.02(14) . 2_655 ?
C3 N3 C5 111.6(3) . . ?
C3 N3 C7 127.1(3) . . ?
C5 N3 C7 121.3(2) . . ?
C3 N4 C4 111.7(3) . . ?
C3 N4 C6 125.9(2) . . ?
C4 N4 C6 122.3(3) . . ?
O2 C1 W1 175.7(2) . . ?
O4 C2 W1 173.6(2) . . ?
N3 C3 W1 129.1(2) . . ?
N4 C3 W1 127.4(2) . . ?
N4 C3 N3 103.4(2) . . ?
N4 C4 H4 126.8 . . ?
C5 C4 N4 106.5(3) . . ?
C5 C4 H4 126.8 . . ?
N3 C5 H5 126.6 . . ?
C4 C5 N3 106.9(3) . . ?
C4 C5 H5 126.6 . . ?
N4 C6 H6A 109.5 . . ?
N4 C6 H6B 109.5 . . ?
N4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C7 H7A 109.5 . . ?
N3 C7 H7B 109.5 . . ?
N3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

_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_p-1
_database_code_depnum_ccdc_archive 'CCDC 2224919'
loop_
_audit_author_name
_audit_author_address
'Milan Gembicky'
;University of California San Diego
United States of America
;
_audit_update_record             
;
2022-12-07 deposited with the CCDC.	2024-12-03 downloaded from the CCDC.
;
_audit_creation_date             2022-02-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'2(W), 4(C O), 2(C11 H12 N O), 2(C2 H3 O2), 2(C4 H8 O)'
_chemical_formula_sum            'C38 H46 N2 O12 W2'
_chemical_formula_weight         1090.47
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
W W -0.8490 6.8722 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9455(7)
_cell_length_b                   10.6935(7)
_cell_length_c                   12.0535(8)
_cell_angle_alpha                66.560(2)
_cell_angle_beta                 71.070(2)
_cell_angle_gamma                71.049(2)
_cell_volume                     974.88(12)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4400
_cell_measurement_temperature    100
_cell_measurement_theta_max      22.736
_cell_measurement_theta_min      2.471
_shelx_estimated_absorpt_T_max   0.916
_shelx_estimated_absorpt_T_min   0.797
_exptl_absorpt_coefficient_mu    5.959
_exptl_absorpt_correction_T_max  0.490
_exptl_absorpt_correction_T_min  0.352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 44892 reflections, Rint = 0.1158
 (20992 with I > 3sig(I), Rint = 0.0834)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.857
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.015
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0834
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            3992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.406
_diffrn_reflns_theta_min         2.131
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3397
_reflns_number_total             3992
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.988
_refine_diff_density_min         -1.639
_refine_diff_density_rms         0.162
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3992
_refine_ls_number_restraints     85
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0419
_refine_ls_restrained_S_all      1.021
_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)+(0.0546P)²+2.0691P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0962
_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
2. Restrained distances
 C4T-C3T \\sim C4S-C3S \\sim C3T-C2T \\sim C3S-C2S \\sim C2T-C1T \\sim C2S-C1S
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 O1S, C1S, C2S, C3S, C4S, C4T, O1T, C1T, C2T, C3T
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Same fragment restrains
{O1S, C1S, C2S, C3S, C4S} sigma for 1-2: 0.005, 1-3: 0.01
as in
{O1T, C1T, C2T, C3T, C4T}
5. Others
 Sof(O1T)=Sof(C1T)=Sof(H1TA)=Sof(H1TB)=Sof(C2T)=Sof(H2TA)=Sof(H2TB)=Sof(C3T)=
 Sof(H3TA)=Sof(H3TB)=Sof(C4T)=Sof(H4TA)=Sof(H4TB)=1-FVAR(1)
 Sof(O1S)=Sof(C1S)=Sof(H1SA)=Sof(H1SB)=Sof(C2S)=Sof(H2SA)=Sof(H2SB)=Sof(C3S)=
 Sof(H3SA)=Sof(H3SB)=Sof(C4S)=Sof(H4SA)=Sof(H4SB)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C1S(H1SA,H1SB), C2S(H2SA,H2SB), C3S(H3SA,H3SB), C4S(H4SA,H4SB),
 C1T(H1TA,H1TB), C2T(H2TA,H2TB), C3T(H3TA,H3TB), C4T(H4TA,H4TB)
6.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
6.c X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
6.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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
W1 W 0.79338(3) 0.71527(3) 0.04394(2) 0.03371(11) Uani 1 1 d . . . . .
O1 O 0.7898(7) 0.8566(6) -0.2365(5) 0.0543(14) Uani 1 1 d . . . . .
O2 O 0.4307(6) 0.7831(5) 0.0377(5) 0.0500(13) Uani 1 1 d . . . . .
O3 O 0.7836(7) 0.5962(5) 0.2422(4) 0.0407(11) Uani 1 1 d . . . . .
O4 O 0.8385(6) 0.5064(4) 0.0523(4) 0.0346(10) Uani 1 1 d . . . . .
O5 O 0.9493(6) 0.3555(5) -0.0509(5) 0.0401(11) Uani 1 1 d . . . . .
N1 N 0.7117(8) 0.5947(6) 0.4409(5) 0.0456(15) Uani 1 1 d . . . . .
H1 H 0.650845 0.643706 0.490046 0.055 Uiso 1 1 calc R U . . .
C1 C 0.8687(9) 0.9279(7) -0.0328(7) 0.0403(16) Uani 1 1 d . . . . .
H1A H 0.794979 0.953148 -0.083882 0.048 Uiso 1 1 calc R U . . .
H1B H 0.978349 0.934646 -0.069422 0.048 Uiso 1 1 calc R U . . .
C2 C 0.8152(9) 0.8802(6) 0.0977(7) 0.0393(16) Uani 1 1 d . . . . .
H2 H 0.887129 0.854424 0.150279 0.047 Uiso 1 1 calc R U . . .
C3 C 0.6511(9) 0.8722(7) 0.1471(7) 0.0408(16) Uani 1 1 d . . . . .
H3 H 0.576510 0.914157 0.094477 0.049 Uiso 1 1 calc R U . . .
C4 C 0.5943(10) 0.7975(7) 0.2825(7) 0.0456(18) Uani 1 1 d . . . . .
H4A H 0.482387 0.787094 0.298766 0.055 Uiso 1 1 calc R U . . .
H4B H 0.593162 0.853020 0.331826 0.055 Uiso 1 1 calc R U . . .
C5 C 0.7051(9) 0.6554(7) 0.3208(6) 0.0406(16) Uani 1 1 d . . . . .
C6 C 0.8050(10) 0.4605(8) 0.4994(6) 0.0430(17) Uani 1 1 d . . . . .
C7 C 0.9321(10) 0.3832(9) 0.4348(7) 0.053(2) Uani 1 1 d . . . . .
H7 H 0.962224 0.418227 0.346784 0.063 Uiso 1 1 calc R U . . .
C8 C 1.0146(10) 0.2552(10) 0.4991(8) 0.061(2) Uani 1 1 d . . . . .
H8 H 1.103489 0.202511 0.455263 0.073 Uiso 1 1 calc R U . . .
C9 C 0.9695(11) 0.2034(10) 0.6254(7) 0.058(2) Uani 1 1 d . . . . .
H9 H 1.024191 0.113103 0.668895 0.070 Uiso 1 1 calc R U . . .
C10 C 0.8466(12) 0.2807(10) 0.6891(8) 0.062(2) Uani 1 1 d . . . . .
H10 H 0.818461 0.245445 0.777196 0.075 Uiso 1 1 calc R U . . .
C11 C 0.7626(11) 0.4097(9) 0.6270(7) 0.053(2) Uani 1 1 d . . . . .
H11 H 0.676139 0.463003 0.671752 0.064 Uiso 1 1 calc R U . . .
C12 C 0.7977(9) 0.8015(7) -0.1327(7) 0.0394(16) Uani 1 1 d . . . . .
C13 C 0.5656(10) 0.7556(7) 0.0444(6) 0.0399(17) Uani 1 1 d . . . . .
C14 C 0.8415(8) 0.4551(7) -0.0274(6) 0.0346(14) Uani 1 1 d . . . . .
C15 C 0.7096(9) 0.5137(8) -0.0974(7) 0.0438(17) Uani 1 1 d . . . . .
H15A H 0.616188 0.569702 -0.054904 0.066 Uiso 1 1 calc R U . . .
H15B H 0.676829 0.436846 -0.101344 0.066 Uiso 1 1 calc R U . . .
H15C H 0.749442 0.572890 -0.181710 0.066 Uiso 1 1 calc R U . . .
O1S O 0.5214(15) 0.7264(13) 0.6130(11) 0.057(3) Uani 0.583(17) 1 d D . P A 1
C1S C 0.498(2) 0.841(2) 0.648(2) 0.072(6) Uani 0.583(17) 1 d D . P A 1
H1SA H 0.495152 0.927646 0.575507 0.087 Uiso 0.583(17) 1 calc R U P A 1
H1SB H 0.587157 0.829378 0.685925 0.087 Uiso 0.583(17) 1 calc R U P A 1
C2S C 0.341(2) 0.847(4) 0.740(3) 0.117(10) Uani 0.583(17) 1 d D . P A 1
H2SA H 0.356788 0.794403 0.825380 0.140 Uiso 0.583(17) 1 calc R U P A 1
H2SB H 0.285327 0.945459 0.734719 0.140 Uiso 0.583(17) 1 calc R U P A 1
C3S C 0.2451(19) 0.784(2) 0.7078(19) 0.063(5) Uani 0.583(17) 1 d D . P A 1
H3SA H 0.188043 0.853019 0.642337 0.076 Uiso 0.583(17) 1 calc R U P A 1
H3SB H 0.165463 0.741404 0.781190 0.076 Uiso 0.583(17) 1 calc R U P A 1
C4S C 0.375(2) 0.678(2) 0.662(2) 0.111(9) Uani 0.583(17) 1 d D . P A 1
H4SA H 0.389366 0.588318 0.731306 0.134 Uiso 0.583(17) 1 calc R U P A 1
H4SB H 0.346031 0.661864 0.597244 0.134 Uiso 0.583(17) 1 calc R U P A 1
O1T O 0.4758(15) 0.7852(17) 0.5709(13) 0.047(4) Uani 0.417(17) 1 d D . P A 2
C1T C 0.474(2) 0.793(4) 0.683(2) 0.090(11) Uani 0.417(17) 1 d D . P A 2
H1TA H 0.534982 0.861367 0.670299 0.108 Uiso 0.417(17) 1 calc R U P A 2
H1TB H 0.523369 0.700219 0.736458 0.108 Uiso 0.417(17) 1 calc R U P A 2
C2T C 0.301(3) 0.837(3) 0.743(2) 0.066(6) Uani 0.417(17) 1 d D . P A 2
H2TA H 0.281022 0.787874 0.833491 0.079 Uiso 0.417(17) 1 calc R U P A 2
H2TB H 0.271364 0.938969 0.727635 0.079 Uiso 0.417(17) 1 calc R U P A 2
C3T C 0.206(2) 0.800(4) 0.687(2) 0.070(7) Uani 0.417(17) 1 d D . P A 2
H3TA H 0.099088 0.866104 0.683090 0.084 Uiso 0.417(17) 1 calc R U P A 2
H3TB H 0.190431 0.703511 0.732058 0.084 Uiso 0.417(17) 1 calc R U P A 2
C4T C 0.3121(19) 0.813(2) 0.5625(16) 0.056(5) Uani 0.417(17) 1 d D . P A 2
H4TA H 0.300304 0.746294 0.529952 0.067 Uiso 0.417(17) 1 calc R U P A 2
H4TB H 0.281409 0.909130 0.505041 0.067 Uiso 0.417(17) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.167(9) . ?
O2 C13 1.168(9) . ?
O3 C5 1.245(8) . ?
O4 C14 1.271(8) . ?
O5 C14 1.242(8) . ?
N1 H1 0.8800 . ?
N1 C5 1.343(9) . ?
N1 C6 1.433(10) . ?
C1 H1A 0.9500 . ?
C1 H1B 0.9500 . ?
C1 C2 1.412(10) . ?
C2 H2 0.9500 . ?
C2 C3 1.411(11) . ?
C3 H3 0.9500 . ?
C3 C4 1.499(10) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.505(10) . ?
C6 C7 1.382(11) . ?
C6 C11 1.376(10) . ?
C7 H7 0.9500 . ?
C7 C8 1.374(12) . ?
C8 H8 0.9500 . ?
C8 C9 1.366(11) . ?
C9 H9 0.9500 . ?
C9 C10 1.360(13) . ?
C10 H10 0.9500 . ?
C10 C11 1.378(12) . ?
C11 H11 0.9500 . ?
C14 C15 1.497(10) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O1S C1S 1.384(15) . ?
O1S C4S 1.425(15) . ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?
C1S C2S 1.486(12) . ?
C2S H2SA 0.9900 . ?
C2S H2SB 0.9900 . ?
C2S C3S 1.460(12) . ?
C3S H3SA 0.9900 . ?
C3S H3SB 0.9900 . ?
C3S C4S 1.473(13) . ?
C4S H4SA 0.9900 . ?
C4S H4SB 0.9900 . ?
O1T C1T 1.384(15) . ?
O1T C4T 1.424(15) . ?
C1T H1TA 0.9900 . ?
C1T H1TB 0.9900 . ?
C1T C2T 1.483(12) . ?
C2T H2TA 0.9900 . ?
C2T H2TB 0.9900 . ?
C2T C3T 1.459(12) . ?
C3T H3TA 0.9900 . ?
C3T H3TB 0.9900 . ?
C3T C4T 1.471(13) . ?
C4T H4TA 0.9900 . ?
C4T H4TB 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 H1 115.8 . . ?
C5 N1 C6 128.4(6) . . ?
C6 N1 H1 115.8 . . ?
H1A C1 H1B 120.0 . . ?
C2 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
C1 C2 H2 121.2 . . ?
C1 C2 C3 117.6(7) . . ?
C3 C2 H2 121.2 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.1(7) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
C3 C4 C5 110.0(6) . . ?
H4A C4 H4B 108.2 . . ?
C5 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
O3 C5 N1 122.1(7) . . ?
O3 C5 C4 119.6(6) . . ?
N1 C5 C4 118.3(6) . . ?
C7 C6 N1 123.5(6) . . ?
C11 C6 N1 116.4(7) . . ?
C11 C6 C7 120.1(7) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 C6 119.4(7) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.5(8) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.1(8) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.5(8) . . ?
C11 C10 H10 119.7 . . ?
C6 C11 H11 120.3 . . ?
C10 C11 C6 119.4(8) . . ?
C10 C11 H11 120.3 . . ?
O4 C14 C15 120.1(6) . . ?
O5 C14 O4 123.3(6) . . ?
O5 C14 C15 116.5(6) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1S O1S C4S 108.2(9) . . ?
O1S C1S H1SA 110.6 . . ?
O1S C1S H1SB 110.6 . . ?
O1S C1S C2S 105.8(11) . . ?
H1SA C1S H1SB 108.7 . . ?
C2S C1S H1SA 110.6 . . ?
C2S C1S H1SB 110.6 . . ?
C1S C2S H2SA 110.6 . . ?
C1S C2S H2SB 110.6 . . ?
H2SA C2S H2SB 108.7 . . ?
C3S C2S C1S 105.6(10) . . ?
C3S C2S H2SA 110.6 . . ?
C3S C2S H2SB 110.6 . . ?
C2S C3S H3SA 111.8 . . ?
C2S C3S H3SB 111.8 . . ?
C2S C3S C4S 100.1(13) . . ?
H3SA C3S H3SB 109.5 . . ?
C4S C3S H3SA 111.8 . . ?
C4S C3S H3SB 111.8 . . ?
O1S C4S C3S 108.6(10) . . ?
O1S C4S H4SA 110.0 . . ?
O1S C4S H4SB 110.0 . . ?
C3S C4S H4SA 110.0 . . ?
C3S C4S H4SB 110.0 . . ?
H4SA C4S H4SB 108.4 . . ?
C1T O1T C4T 108.0(9) . . ?
O1T C1T H1TA 110.4 . . ?
O1T C1T H1TB 110.4 . . ?
O1T C1T C2T 106.7(11) . . ?
H1TA C1T H1TB 108.6 . . ?
C2T C1T H1TA 110.4 . . ?
C2T C1T H1TB 110.4 . . ?
C1T C2T H2TA 110.4 . . ?
C1T C2T H2TB 110.4 . . ?
H2TA C2T H2TB 108.6 . . ?
C3T C2T C1T 106.4(11) . . ?
C3T C2T H2TA 110.4 . . ?
C3T C2T H2TB 110.4 . . ?
C2T C3T H3TA 111.7 . . ?
C2T C3T H3TB 111.7 . . ?
C2T C3T C4T 100.5(13) . . ?
H3TA C3T H3TB 109.4 . . ?
C4T C3T H3TA 111.7 . . ?
C4T C3T H3TB 111.7 . . ?
O1T C4T C3T 108.8(11) . . ?
O1T C4T H4TA 109.9 . . ?
O1T C4T H4TB 109.9 . . ?
C3T C4T H4TA 109.9 . . ?
C3T C4T H4TB 109.9 . . ?
H4TA C4T H4TB 108.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C6 C7 C8 -180.0(8) . . . . ?
N1 C6 C11 C10 179.6(8) . . . . ?
C1 C2 C3 C4 168.3(6) . . . . ?
C2 C3 C4 C5 -49.4(9) . . . . ?
C3 C4 C5 O3 -25.7(10) . . . . ?
C3 C4 C5 N1 156.5(7) . . . . ?
C5 N1 C6 C7 14.8(12) . . . . ?
C5 N1 C6 C11 -165.6(8) . . . . ?
C6 N1 C5 O3 1.1(12) . . . . ?
C6 N1 C5 C4 178.9(7) . . . . ?
C6 C7 C8 C9 1.3(14) . . . . ?
C7 C6 C11 C10 -0.8(13) . . . . ?
C7 C8 C9 C10 -2.7(15) . . . . ?
C8 C9 C10 C11 2.3(15) . . . . ?
C9 C10 C11 C6 -0.5(14) . . . . ?
C11 C6 C7 C8 0.4(13) . . . . ?
O1S C1S C2S C3S -28(3) . . . . ?
C1S O1S C4S C3S 12(3) . . . . ?
C1S C2S C3S C4S 34(3) . . . . ?
C2S C3S C4S O1S -29(2) . . . . ?
C4S O1S C1S C2S 10(3) . . . . ?
O1T C1T C2T C3T 22(4) . . . . ?
C1T O1T C4T C3T -16(3) . . . . ?
C1T C2T C3T C4T -30(3) . . . . ?
C2T C3T C4T O1T 28(3) . . . . ?
C4T O1T C1T C2T -4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
