# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_TPyP_sublimed_100K
_database_code_depnum_ccdc_archive 'CCDC 1919802'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;University of Liverpool
United Kingdom
;
_audit_update_record             
;
2019-05-30 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;
_audit_creation_date             2019-05-15
_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            TPyP
_chemical_name_systematic        TPyP
_chemical_formula_moiety         'C36 H22 N4'
_chemical_formula_sum            'C36 H22 N4'
_chemical_formula_weight         510.57
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C40 H10 N4'
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'

_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                   3.9510(2)
_cell_length_b                   10.9411(7)
_cell_length_c                   26.7651(14)
_cell_angle_alpha                90
_cell_angle_beta                 91.814(5)
_cell_angle_gamma                90
_cell_volume                     1156.43(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5128
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.3830
_cell_measurement_theta_min      1.9930
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.274
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.058
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            2347
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.416
_diffrn_reflns_theta_min         1.522
_diffrn_ambient_temperature      100.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  15.00   1.00   40.00    --  -20.00 -68.00   0.00  125
  2  ω   -110.00  15.00   1.00   40.00    --  -20.00 -68.00 120.00  125
  3  ω   -110.00  15.00   1.00   40.00    --  -20.00 -68.00 240.00  125
  4  ω   -110.00  15.00   1.00   40.00    --  -20.00 -30.00  90.00  125
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0137506000
_diffrn_orient_matrix_UB_12      0.0482177000
_diffrn_orient_matrix_UB_13      0.0175316000
_diffrn_orient_matrix_UB_21      -0.0217784000
_diffrn_orient_matrix_UB_22      0.0423910000
_diffrn_orient_matrix_UB_23      -0.0198901000
_diffrn_orient_matrix_UB_31      -0.1778062000
_diffrn_orient_matrix_UB_32      -0.0088830000
_diffrn_orient_matrix_UB_33      0.0002032000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2031
_reflns_number_total             2347
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 _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 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0704
_refine_ls_restrained_S_all      1.118
_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)+(0.0681P)²+2.2188P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1761
_refine_ls_wR_factor_ref         0.1819
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.894(3)
 0.106(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15),
 C16(H16), C17(H17), C18(H18)
;
_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
N1 N 0.1308(7) 1.0715(2) 0.61449(9) 0.0201(6) Uani 1 1 d . . . . .
N2 N 0.8229(7) 0.2926(2) 0.75013(9) 0.0219(6) Uani 1 1 d . . . . .
C1 C 0.2195(7) 0.6617(2) 0.44351(10) 0.0161(6) Uani 1 1 d . . . . .
H1 H 0.1196 0.7070 0.4166 0.019 Uiso 1 1 calc R . . . .
C2 C 0.2092(7) 0.7070(3) 0.49035(10) 0.0154(6) Uani 1 1 d . . . . .
H2 H 0.0977 0.7827 0.4955 0.018 Uiso 1 1 calc R . . . .
C3 C 0.3617(7) 0.6443(2) 0.53277(10) 0.0145(6) Uani 1 1 d . . . . .
C4 C 0.3728(7) 0.6942(2) 0.58181(10) 0.0154(6) Uani 1 1 d . . . . .
C5 C 0.4845(7) 0.6218(3) 0.62204(10) 0.0161(6) Uani 1 1 d . . . . .
H5 H 0.4834 0.6550 0.6548 0.019 Uiso 1 1 calc R . . . .
C6 C 0.5982(7) 0.5014(2) 0.61554(10) 0.0162(6) Uani 1 1 d . . . . .
C7 C 0.6212(7) 0.4539(2) 0.56654(10) 0.0152(6) Uani 1 1 d . . . . .
C8 C 0.4955(7) 0.5245(2) 0.52492(9) 0.0145(6) Uani 1 1 d . . . . .
C9 C 0.2781(7) 0.8238(3) 0.59217(10) 0.0165(6) Uani 1 1 d . . . . .
C10 C 0.3891(7) 0.9203(3) 0.56223(10) 0.0168(6) Uani 1 1 d . . . . .
H10 H 0.5182 0.9040 0.5336 0.020 Uiso 1 1 calc R . . . .
C11 C 0.3082(8) 1.0404(3) 0.57480(11) 0.0194(6) Uani 1 1 d . . . . .
H11 H 0.3842 1.1040 0.5538 0.023 Uiso 1 1 calc R . . . .
C12 C 0.0299(8) 0.9791(3) 0.64332(10) 0.0189(6) Uani 1 1 d . . . . .
H12 H -0.0966 0.9986 0.6718 0.023 Uiso 1 1 calc R . . . .
C13 C 0.0982(7) 0.8557(3) 0.63421(10) 0.0168(6) Uani 1 1 d . . . . .
H13 H 0.0230 0.7945 0.6564 0.020 Uiso 1 1 calc R . . . .
C14 C 0.6878(7) 0.4281(3) 0.66113(10) 0.0155(6) Uani 1 1 d . . . . .
C15 C 0.8747(8) 0.4778(3) 0.70152(10) 0.0188(6) Uani 1 1 d . . . . .
H15 H 0.9580 0.5591 0.6999 0.023 Uiso 1 1 calc R . . . .
C16 C 0.9376(8) 0.4076(3) 0.74404(10) 0.0212(6) Uani 1 1 d . . . . .
H16 H 1.0700 0.4428 0.7706 0.025 Uiso 1 1 calc R . . . .
C17 C 0.6374(8) 0.2465(3) 0.71143(10) 0.0208(6) Uani 1 1 d . . . . .
H17 H 0.5487 0.1664 0.7147 0.025 Uiso 1 1 calc R . . . .
C18 C 0.5673(8) 0.3087(3) 0.66697(10) 0.0184(6) Uani 1 1 d . . . . .
H18 H 0.4387 0.2704 0.6408 0.022 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 C11 1.335(4) . ?
N1 C12 1.340(4) . ?
N2 C16 1.349(4) . ?
N2 C17 1.347(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.350(4) . ?
C1 C7 1.442(4) 3_666 ?
C2 H2 0.9500 . ?
C2 C3 1.442(4) . ?
C3 C4 1.421(4) . ?
C3 C8 1.432(4) . ?
C4 C5 1.397(4) . ?
C4 C9 1.495(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.404(4) . ?
C6 C7 1.416(4) . ?
C6 C14 1.493(4) . ?
C7 C1 1.442(4) 3_666 ?
C7 C8 1.431(4) . ?
C8 C8 1.439(5) 3_666 ?
C9 C10 1.404(4) . ?
C9 C13 1.394(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.395(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.399(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.399(4) . ?
C14 C18 1.402(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C17 C18 1.391(4) . ?
C18 H18 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
C11 N1 C12 116.1(3) . . ?
C17 N2 C16 115.6(2) . . ?
C2 C1 H1 119.3 . . ?
C2 C1 C7 121.4(3) . 3_666 ?
C7 C1 H1 119.3 3_666 . ?
C1 C2 H2 118.9 . . ?
C1 C2 C3 122.2(3) . . ?
C3 C2 H2 118.9 . . ?
C4 C3 C2 123.0(2) . . ?
C4 C3 C8 119.1(2) . . ?
C8 C3 C2 117.8(2) . . ?
C3 C4 C9 122.3(2) . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 C9 118.0(2) . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 122.1(2) . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C7 119.3(2) . . ?
C5 C6 C14 118.1(2) . . ?
C7 C6 C14 122.7(2) . . ?
C6 C7 C1 122.4(2) . 3_666 ?
C6 C7 C8 119.5(3) . . ?
C8 C7 C1 118.1(2) . 3_666 ?
C3 C8 C8 119.8(3) . 3_666 ?
C7 C8 C3 120.0(2) . . ?
C7 C8 C8 120.2(3) . 3_666 ?
C10 C9 C4 121.5(3) . . ?
C13 C9 C4 121.6(3) . . ?
C13 C9 C10 116.6(3) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.5(3) . . ?
C11 C10 H10 120.3 . . ?
N1 C11 C10 124.2(3) . . ?
N1 C11 H11 117.9 . . ?
C10 C11 H11 117.9 . . ?
N1 C12 H12 117.8 . . ?
N1 C12 C13 124.4(3) . . ?
C13 C12 H12 117.8 . . ?
C9 C13 C12 119.2(3) . . ?
C9 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C15 C14 C6 121.9(3) . . ?
C15 C14 C18 116.7(3) . . ?
C18 C14 C6 121.3(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 H15 120.2 . . ?
N2 C16 C15 124.3(3) . . ?
N2 C16 H16 117.9 . . ?
C15 C16 H16 117.9 . . ?
N2 C17 H17 117.8 . . ?
N2 C17 C18 124.3(3) . . ?
C18 C17 H17 117.8 . . ?
C14 C18 H18 120.3 . . ?
C17 C18 C14 119.5(3) . . ?
C17 C18 H18 120.3 . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.498
_oxdiff_exptl_absorpt_empirical_full_min 0.736
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.894(3)
2 0.106(3)

####################################################################### 
# 
# 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_TBAP_C2c_Desolvated_Structure_200K
_database_code_depnum_ccdc_archive 'CCDC 1919804'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;University of Liverpool
United Kingdom
;
_audit_update_record             
;
2019-05-30 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT027_ck_tbap_ace_200k    
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      25.00 Degree
RESPONSE: The crystal was weakly diffracting at high angle and a suitable
resolution limit was applied during refinement.  
;
_vrf_PLAT602_ck_tbap_ace_200k    
;
PROBLEM: VERY LARGE Solvent Accessible VOID(S) in Structure        ! Info 
RESPONSE: The crystal structure contains large 1D voids that 
did not contain any ordered electron density. No solvent mask was applied 
during refinement.  
;
_vrf_PLAT049_ck_tbap_ace_200k    
;
PROBLEM: Calculated Density Less Than 1.0 gcm-3 .........     0.7072 Check 
RESPONSE: The crystal structure contains large 1D voids that 
did not contain any ordered electron density. No solvent mask was applied 
during refinement.  
;
# end Validation Reply Form

_audit_creation_date             2018-03-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H26 O8'
_chemical_formula_sum            'C44 H26 O8'
_chemical_formula_weight         682.65
_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 0.0040 0.0020 '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'
O O 0.0130 0.0070 '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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   29.036(4)
_cell_length_b                   28.538(4)
_cell_length_c                   3.8714(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.979(8)
_cell_angle_gamma                90
_cell_volume                     3206.0(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7493
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      43.569
_cell_measurement_theta_min      3.231
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.058
_exptl_absorpt_correction_T_max  0.8630
_exptl_absorpt_correction_T_min  0.7821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1228 before and 0.0457 after correction.
The Ratio of minimum to maximum transmission is 0.9063.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    0.707
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            11767
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.984
_diffrn_reflns_theta_min         1.530
_diffrn_ambient_temperature      200.15
_diffrn_detector_area_resol_mean 10.42
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_source                   'Advanced Light Source, station 11.3.1'
_diffrn_measurement_device_type  'Bruker D8 with PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7749
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2616
_reflns_number_total             3040
_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 (?, 2016)'
_computing_data_collection       'Bruker APEX3 Bruker-AXS, Madison WI'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         3040
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.071
_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)+(0.0737P)²+1.1743P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1356
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C11(H11)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.69183(3) 0.75047(4) 0.4433(3) 0.0533(3) Uani 1 1 d . . . . .
O2 O 0.73702(3) 0.69922(4) 0.7273(3) 0.0555(3) Uani 1 1 d . . . . .
H2 H 0.7575 0.7181 0.6683 0.083 Uiso 1 1 calc GR . . . .
C2 C 0.65736(4) 0.68444(4) 0.6954(3) 0.0322(3) Uani 1 1 d . . . . .
C3 C 0.66283(4) 0.64265(4) 0.8751(3) 0.0320(3) Uani 1 1 d . . . . .
H3 H 0.6927 0.6330 0.9550 0.038 Uiso 1 1 calc R . . . .
C4 C 0.62493(4) 0.61488(4) 0.9385(3) 0.0288(3) Uani 1 1 d . . . . .
H4 H 0.6289 0.5865 1.0638 0.035 Uiso 1 1 calc R . . . .
C5 C 0.58089(4) 0.62819(4) 0.8202(3) 0.0252(3) Uani 1 1 d . . . . .
C6 C 0.57585(4) 0.67055(4) 0.6447(3) 0.0296(3) Uani 1 1 d . . . . .
H6 H 0.5460 0.6804 0.5662 0.036 Uiso 1 1 calc R . . . .
C7 C 0.61359(4) 0.69862(4) 0.5827(3) 0.0331(3) Uani 1 1 d . . . . .
H7 H 0.6096 0.7275 0.4635 0.040 Uiso 1 1 calc R . . . .
C9 C 0.53952(4) 0.59946(4) 0.8993(3) 0.0240(3) Uani 1 1 d . . . . .
C10 C 0.53889(3) 0.55006(4) 0.8800(3) 0.0224(3) Uani 1 1 d . . . . .
C12 C 0.5000 0.52510(5) 1.0000 0.0215(3) Uani 1 2 d S T P . .
C8 C 0.5000 0.62252(6) 1.0000 0.0254(4) Uani 1 2 d S T P . .
H8 H 0.5000 0.6558 1.0000 0.030 Uiso 1 2 calc RS T P . .
C11 C 0.57494(4) 0.52357(4) 0.7291(3) 0.0244(3) Uani 1 1 d . . . . .
H11 H 0.5996 0.5397 0.6261 0.029 Uiso 1 1 calc R . . . .
C1 C 0.69792(4) 0.71379(5) 0.6171(4) 0.0372(3) Uani 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 1.2536(16) . ?
O2 H2 0.8400 . ?
O2 C1 1.2691(17) . ?
C2 C3 1.3871(18) . ?
C2 C7 1.3898(18) . ?
C2 C1 1.4849(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.3847(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.3959(16) . ?
C5 C6 1.3919(17) . ?
C5 C9 1.4948(15) . ?
C6 H6 0.9500 . ?
C6 C7 1.3850(16) . ?
C7 H7 0.9500 . ?
C9 C10 1.4119(16) . ?
C9 C8 1.3901(13) . ?
C10 C12 1.4262(13) . ?
C10 C11 1.4321(15) . ?
C12 C10 1.4262(13) 2_657 ?
C12 C12 1.433(3) 5_667 ?
C8 C9 1.3902(13) 2_657 ?
C8 H8 0.9500 . ?
C11 C11 1.345(2) 6_565 ?
C11 H11 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
C1 O2 H2 109.5 . . ?
C3 C2 C7 119.70(11) . . ?
C3 C2 C1 120.64(12) . . ?
C7 C2 C1 119.66(12) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.20(11) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.71(11) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C9 121.14(10) . . ?
C6 C5 C4 118.43(10) . . ?
C6 C5 C9 120.31(10) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 121.09(11) . . ?
C7 C6 H6 119.5 . . ?
C2 C7 H7 120.1 . . ?
C6 C7 C2 119.84(11) . . ?
C6 C7 H7 120.1 . . ?
C10 C9 C5 123.08(10) . . ?
C8 C9 C5 118.35(11) . . ?
C8 C9 C10 118.57(10) . . ?
C9 C10 C12 119.36(10) . . ?
C9 C10 C11 122.70(10) . . ?
C12 C10 C11 117.87(11) . . ?
C10 C12 C10 120.08(14) 2_657 . ?
C10 C12 C12 119.96(7) . 5_667 ?
C10 C12 C12 119.96(7) 2_657 5_667 ?
C9 C8 C9 123.48(15) . 2_657 ?
C9 C8 H8 118.3 . . ?
C9 C8 H8 118.3 2_657 . ?
C10 C11 H11 119.1 . . ?
C11 C11 C10 121.85(6) 6_565 . ?
C11 C11 H11 119.1 6_565 . ?
O1 C1 O2 124.18(12) . . ?
O1 C1 C2 118.86(12) . . ?
O2 C1 C2 116.95(12) . . ?

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
O2 H2 O1 0.84 1.79 2.6189(13) 169.6 7_666

_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_TBAP_C2c_Desolvated_Structure_400K_publ
_database_code_depnum_ccdc_archive 'CCDC 1919805'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;University of Liverpool
United Kingdom
;
_audit_update_record             
;
2019-05-30 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT602_tbap_400k           
;
PROBLEM: VERY LARGE Solvent Accessible VOID(S) in Structure ! Info
RESPONSE: The crystal structure contains large 1D voids that 
did not contain any ordered electron density. No solvent mask was applied 
during refinement.
;
_vrf_PLAT049_tbap_400k           
;
PROBLEM: Calculated Density Less Than 1.0 gcm-3 ......... 0.6780 Check
RESPONSE: The crystal structure contains large 1D voids that 
did not contain any ordered electron density. No solvent mask was applied 
during refinement. 
;
# end Validation Reply Form

_audit_creation_date             2018-03-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H26 O8'
_chemical_formula_sum            'C44 H26 O8'
_chemical_formula_weight         682.65
_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 0.0040 0.0020 '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'
O O 0.0130 0.0070 '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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   29.16(9)
_cell_length_b                   28.69(8)
_cell_length_c                   3.998(13)
_cell_angle_alpha                90
_cell_angle_beta                 91.92(5)
_cell_angle_gamma                90
_cell_volume                     3343(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    150
_cell_measurement_temperature    400(2)
_cell_measurement_theta_max      14.32
_cell_measurement_theta_min      2.90
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.056
_exptl_absorpt_correction_T_max  0.8628
_exptl_absorpt_correction_T_min  0.7265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1726 before and 0.0503 after correction.
The Ratio of minimum to maximum transmission is 0.8420.
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    0.678
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            10220
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        27.807
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         1.529
_diffrn_ambient_temperature      400.15
_diffrn_detector_area_resol_mean 10.42
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 with PHOTON II detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_wavelength     0.7749
_diffrn_source                   'Advanced Light Source, station 11.3.1'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2480
_reflns_number_total             3134
_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 (?, 2016)'
_computing_data_collection       'Bruker APEX3 Bruker-AXS, Madison WI'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         3134
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0512
_refine_ls_restrained_S_all      1.111
_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)+(0.1060P)²+0.2660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1651
_refine_ls_wR_factor_ref         0.1746
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), C4(H4), C6(H6), C7(H7), C3(H3)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
C10 C 0.03874(3) 0.44999(4) 0.3793(3) 0.0450(3) Uani 1 1 d . . . . .
C8 C 0.0000 0.37758(6) 0.5000 0.0523(4) Uani 1 2 d S T P . .
H8 H 0.0000 0.3452 0.5000 0.063 Uiso 1 2 calc RS T P . .
C12 C 0.0000 0.47488(5) 0.5000 0.0429(4) Uani 1 2 d S T P . .
C9 C 0.03938(4) 0.40054(4) 0.3985(3) 0.0484(3) Uani 1 1 d . . . . .
C5 C 0.08066(4) 0.37186(4) 0.3181(3) 0.0516(3) Uani 1 1 d . . . . .
C11 C 0.07447(4) 0.47649(4) 0.2293(3) 0.0506(3) Uani 1 1 d . . . . .
H11 H 0.0983 0.4608 0.1292 0.061 Uiso 1 1 calc R . . . .
C2 C 0.15703(5) 0.31579(5) 0.1912(4) 0.0656(4) Uani 1 1 d . . . . .
C4 C 0.12468(4) 0.38477(4) 0.4332(3) 0.0600(4) Uani 1 1 d . . . . .
H4 H 0.1287 0.4122 0.5543 0.072 Uiso 1 1 calc R . . . .
C6 C 0.07575(4) 0.32999(4) 0.1453(3) 0.0611(4) Uani 1 1 d . . . . .
H6 H 0.0467 0.3205 0.0704 0.073 Uiso 1 1 calc R . . . .
O1 O 0.19098(4) 0.24960(5) -0.0501(4) 0.1150(5) Uani 1 1 d . . . . .
H1 H 0.2156 0.2365 -0.0782 0.138 Uiso 1 1 calc GR . . . .
C7 C 0.11340(5) 0.30210(5) 0.0823(4) 0.0691(4) Uani 1 1 d . . . . .
H7 H 0.1094 0.2742 -0.0331 0.083 Uiso 1 1 calc R . . . .
C3 C 0.16244(4) 0.35707(5) 0.3686(4) 0.0667(4) Uani 1 1 d . . . . .
H3 H 0.1915 0.3663 0.4449 0.080 Uiso 1 1 calc R . . . .
O2 O 0.23697(4) 0.30078(5) 0.2133(4) 0.1145(5) Uani 1 1 d . . . . .
C1 C 0.19779(5) 0.28663(6) 0.1147(4) 0.0797(5) Uani 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
C10 C12 1.433(3) . ?
C10 C9 1.421(4) . ?
C10 C11 1.437(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.396(3) 2_556 ?
C8 C9 1.396(3) . ?
C12 C10 1.434(3) 2_556 ?
C12 C12 1.441(5) 5_566 ?
C9 C5 1.502(3) . ?
C5 C4 1.399(4) . ?
C5 C6 1.391(4) . ?
C11 C11 1.349(4) 6_565 ?
C11 H11 0.9300 . ?
C2 C7 1.388(4) . ?
C2 C3 1.387(4) . ?
C2 C1 1.493(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.389(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.388(3) . ?
O1 H1 0.8200 . ?
O1 C1 1.262(3) . ?
C7 H7 0.9300 . ?
C3 H3 0.9300 . ?
O2 C1 1.263(4) . ?

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
C12 C10 C11 117.9(2) . . ?
C9 C10 C12 119.23(13) . . ?
C9 C10 C11 122.85(13) . . ?
C9 C8 H8 118.2 2_556 . ?
C9 C8 H8 118.2 . . ?
C9 C8 C9 123.7(2) . 2_556 ?
C10 C12 C10 120.2(2) . 2_556 ?
C10 C12 C12 119.88(11) 2_556 5_566 ?
C10 C12 C12 119.88(11) . 5_566 ?
C10 C9 C5 123.01(14) . . ?
C8 C9 C10 118.52(14) . . ?
C8 C9 C5 118.5(2) . . ?
C4 C5 C9 121.2(2) . . ?
C6 C5 C9 120.65(16) . . ?
C6 C5 C4 118.03(12) . . ?
C10 C11 H11 119.0 . . ?
C11 C11 C10 121.95(11) 6_565 . ?
C11 C11 H11 119.0 6_565 . ?
C7 C2 C1 120.3(2) . . ?
C3 C2 C7 119.32(13) . . ?
C3 C2 C1 120.37(19) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 C5 120.8(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.28(18) . . ?
C7 C6 H6 119.4 . . ?
C1 O1 H1 109.5 . . ?
C2 C7 C6 120.1(2) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C2 C3 C4 120.43(18) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
O1 C1 C2 117.8(2) . . ?
O1 C1 O2 123.92(14) . . ?
O2 C1 C2 118.3(2) . . ?

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
O1 H1 O2 0.82 1.84 2.649(6) 166.7 7

_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_TBAP_DMF_CHCl3_200K_publ
_database_code_depnum_ccdc_archive 'CCDC 1919807'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;University of Liverpool
United Kingdom
;
_audit_update_record             
;
2019-05-30 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_CHEMW03_TBAP_DMF_CHCl3_200K_publ 
;
PROBLEM: ALERT: The ratio of given/expected molecular weight as
RESPONSE: In the crystal structure, there are large 1-D voids that 
contain disordered electron density that could not be accurately 
modelled. It was therefore necessary to use the SQUEEZE routine 
in Platon during the final refinement cycles. SQUEEZE removed 
289 e- from two 649 Ang^3 voids. As a result, 6 DMF and 6 CHCl3 
solvent molecules were tentatively added to the unit cell atom 
count.
;
_vrf_PLAT043_TBAP_DMF_CHCl3_200K_publ 
;
PROBLEM: Calculated and Reported Mol. Weight Differ by ..     577.39 Check 
RESPONSE: In the crystal structure, there are large 1-D voids that 
contain disordered electron density that could not be accurately 
modelled. It was therefore necessary to use the SQUEEZE routine 
in Platon during the final refinement cycles. SQUEEZE removed 
289 e- from two 649 Ang^3 voids. As a result, 6 DMF and 6 CHCl3 
solvent molecules were tentatively added to the unit cell atom 
count.
;
_vrf_PLAT051_TBAP_DMF_CHCl3_200K_publ 
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by .      74.43 %     
RESPONSE: In the crystal structure, there are large 1-D voids that 
contain disordered electron density that could not be accurately 
modelled. It was therefore necessary to use the SQUEEZE routine 
in Platon during the final refinement cycles. SQUEEZE removed 
289 e- from two 649 Ang^3 voids. As a result, 6 DMF and 6 CHCl3 
solvent molecules were tentatively added to the unit cell atom 
count.
;
_vrf_PLAT602_TBAP_DMF_CHCl3_200K_publ 
;
PROBLEM: VERY LARGE Solvent Accessible VOID(S) in Structure        ! Info 
RESPONSE: In the crystal structure, there are large 1-D voids that 
contain disordered electron density that could not be accurately 
modelled. It was therefore necessary to use the SQUEEZE routine 
in Platon during the final refinement cycles to mask disordered solvent
in these voids, accounting for this alert. 
;
_vrf_PLAT049_TBAP_DMF_CHCl3_200K_publ 
;
PROBLEM: Calculated Density Less Than 1.0 gcm-3 .........     0.8234 Check 
RESPONSE: In the crystal structure, there are large 1-D voids that 
contain disordered electron density that could not be accurately 
modelled. It was therefore necessary to use the SQUEEZE routine 
in Platon during the final refinement cycles. SQUEEZE removed 
289 e- from two 649 Ang^3 voids. As a result, 6 DMF and 6 CHCl3 
solvent molecules were tentatively added to the unit cell atom 
count.
The estimated density of the solvated structure is 1.439 g/cm3
;
# end Validation Reply Form

_audit_creation_date             2019-03-12
_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         'C44 H26 O8, 3.75(C H Cl3), 3(C3 H7 N O)'
_chemical_formula_sum            'C56.75 H50.75 Cl11.25 N3 O11'
_chemical_formula_weight         1349.56
_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'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 '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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   29.369(3)
_cell_length_b                   27.773(3)
_cell_length_c                   3.8273(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.926(3)
_cell_angle_gamma                90
_cell_volume                     3114.5(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5168
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.856
_cell_measurement_theta_min      2.307
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.951
_exptl_absorpt_coefficient_mu    0.560
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0861 before and 0.0637 after correction. The Ratio of minimum to maximum transmission is 0.7069. 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    1.439
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1383
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            9835
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         2.781
_diffrn_ambient_temperature      200.0
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2566
_reflns_number_total             3253
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         3253
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0664
_refine_ls_restrained_S_all      1.180
_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)+(0.1546P)²+0.6713P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2350
_refine_ls_wR_factor_ref         0.2445
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 Cl3-C13 = Cl4-C13 = Cl4_$1-C13
 1.74 with sigma of 0.02
 C14-Cl2
 1.74 with sigma of 0.02
 C14-Cl1
 1.74 with sigma of 0.02
 Cl1-Cl1_$1
 2.57 with sigma of 0.02
 Cl2-Cl1
 2.65 with sigma of 0.04
 Cl3-Cl4 \\sim Cl3-Cl4_$1 \\sim Cl4_$1-Cl4
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Cl2) = Uanis(C13)
4. Others
 Fixed Sof: C13(0.125) H13(0.125) Cl3(0.125) Cl4(0.25) Cl1(0.125) Cl2(0.0625)
 C14(0.0625) H14(0.0625)
5.a Ternary CH refined with riding coordinates:
 C13(H13), C14(H14)
5.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C6(H6), C3(H3), C7(H7), C4(H4)
5.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
O2 O 0.73662(5) 0.30155(6) 0.2358(5) 0.0565(5) Uani 1 1 d . . . . .
H2 H 0.7572 0.2873 0.1346 0.085 Uiso 1 1 calc GR . . . .
O1 O 0.69255(5) 0.24546(5) -0.0381(4) 0.0520(5) Uani 1 1 d . . . . .
C10 C 0.53850(5) 0.44856(6) 0.3868(4) 0.0248(4) Uani 1 1 d . . . . .
C8 C 0.53908(5) 0.39748(6) 0.4075(4) 0.0255(4) Uani 1 1 d . . . . .
C11 C 0.5000 0.47399(8) 0.5000 0.0239(5) Uani 1 2 d S T P . .
C5 C 0.58037(6) 0.36838(6) 0.3357(4) 0.0272(4) Uani 1 1 d . . . . .
C9 C 0.5000 0.37373(8) 0.5000 0.0274(5) Uani 1 2 d S T P . .
H9 H 0.5000 0.3395 0.5000 0.033 Uiso 1 2 calc RS T P . .
C12 C 0.57408(5) 0.47551(6) 0.2406(4) 0.0262(4) Uani 1 1 d . . . . .
H12 H 0.5983 0.4588 0.1410 0.031 Uiso 1 1 calc R . . . .
C6 C 0.62399(6) 0.38312(6) 0.4602(5) 0.0304(4) Uani 1 1 d . . . . .
H6 H 0.6276 0.4123 0.5885 0.036 Uiso 1 1 calc R . . . .
C2 C 0.65697(6) 0.31210(6) 0.2154(5) 0.0331(5) Uani 1 1 d . . . . .
C3 C 0.61341(6) 0.29652(6) 0.1009(5) 0.0336(4) Uani 1 1 d . . . . .
H3 H 0.6096 0.2667 -0.0187 0.040 Uiso 1 1 calc R . . . .
C7 C 0.66205(6) 0.35566(7) 0.3986(5) 0.0337(4) Uani 1 1 d . . . . .
H7 H 0.6916 0.3664 0.4807 0.040 Uiso 1 1 calc R . . . .
C1 C 0.69752(6) 0.28399(7) 0.1311(5) 0.0391(5) Uani 1 1 d . . . . .
C4 C 0.57547(6) 0.32440(6) 0.1606(5) 0.0318(4) Uani 1 1 d . . . . .
H4 H 0.5459 0.3134 0.0815 0.038 Uiso 1 1 calc R . . . .
C13 C 0.6899(10) 0.5000 -0.165(6) 0.104(3) Uani 0.25 2 d DS T P A 1
H13 H 0.6562 0.5000 -0.1441 0.125 Uiso 0.25 2 calc RS T P A 1
Cl3 Cl 0.7069(5) 0.5000 -0.589(4) 0.227(6) Uani 0.25 2 d DS T P A 1
Cl4 Cl 0.7187(4) 0.4489(3) 0.0046(19) 0.249(6) Uani 0.25 1 d D . . A 1
Cl1 Cl 0.7595(10) 0.4536(3) 0.082(8) 0.326(14) Uiso 0.125 1 d D . . B 2
Cl2 Cl 0.6800(4) 0.5000 -0.212(5) 0.104(3) Uani 0.125 2 d DS T P B 2
C14 C 0.7386(7) 0.5000 -0.163(8) 0.075(8) Uiso 0.125 2 d DS T P B 2
H14 H 0.7518 0.5000 -0.3974 0.090 Uiso 0.125 2 calc RS T P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 H2 0.8400 . ?
O2 C1 1.286(2) . ?
O1 C1 1.254(2) . ?
C10 C8 1.421(2) . ?
C10 C11 1.4255(19) . ?
C10 C12 1.430(2) . ?
C8 C5 1.498(2) . ?
C8 C9 1.3903(19) . ?
C11 C10 1.4255(19) 2_656 ?
C11 C11 1.445(4) 5_666 ?
C5 C6 1.397(2) . ?
C5 C4 1.396(2) . ?
C9 C8 1.3902(19) 2_656 ?
C9 H9 0.9500 . ?
C12 C12 1.360(3) 6_565 ?
C12 H12 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.387(2) . ?
C2 C3 1.393(3) . ?
C2 C7 1.401(3) . ?
C2 C1 1.478(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(2) . ?
C7 H7 0.9500 . ?
C4 H4 0.9500 . ?
C13 H13 1.0000 . ?
C13 Cl3 1.73(2) . ?
C13 Cl4 1.752(13) 6_565 ?
C13 Cl4 1.752(13) . ?
Cl3 C13 2.22(2) 1_554 ?
Cl3 Cl4 2.149(12) 6_564 ?
Cl3 Cl4 2.149(12) 1_554 ?
Cl4 Cl3 2.149(12) 6_566 ?
Cl4 Cl3 2.149(12) 1_556 ?
Cl1 C14 1.687(17) . ?
Cl2 C14 1.718(18) . ?
C14 Cl1 1.687(17) 6_565 ?
C14 H14 1.0000 . ?

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 O2 H2 109.5 . . ?
C8 C10 C11 118.98(15) . . ?
C8 C10 C12 122.56(14) . . ?
C11 C10 C12 118.39(15) . . ?
C10 C8 C5 122.35(14) . . ?
C9 C8 C10 118.75(15) . . ?
C9 C8 C5 118.90(15) . . ?
C10 C11 C10 120.6(2) 2_656 . ?
C10 C11 C11 119.71(10) . 5_666 ?
C10 C11 C11 119.70(10) 2_656 5_666 ?
C6 C5 C8 120.93(15) . . ?
C4 C5 C8 120.13(15) . . ?
C4 C5 C6 118.83(15) . . ?
C8 C9 C8 123.4(2) 2_656 . ?
C8 C9 H9 118.3 2_656 . ?
C8 C9 H9 118.3 . . ?
C10 C12 H12 119.2 . . ?
C12 C12 C10 121.56(9) 6_565 . ?
C12 C12 H12 119.2 6_565 . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.78(16) . . ?
C7 C6 H6 119.6 . . ?
C3 C2 C7 119.34(15) . . ?
C3 C2 C1 120.25(16) . . ?
C7 C2 C1 120.36(16) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.34(16) . . ?
C4 C3 H3 119.8 . . ?
C6 C7 C2 120.02(16) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
O2 C1 C2 116.56(17) . . ?
O1 C1 O2 123.67(16) . . ?
O1 C1 C2 119.76(17) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.63(16) . . ?
C3 C4 H4 119.7 . . ?
Cl3 C13 H13 115.2 . . ?
Cl3 C13 Cl4 100.7(11) . . ?
Cl3 C13 Cl4 100.7(11) . 6_565 ?
Cl4 C13 H13 115.2 6_565 . ?
Cl4 C13 H13 115.2 . . ?
Cl4 C13 Cl4 108.1(13) 6_565 . ?
C13 Cl3 C13 150.5(18) . 1_554 ?
C13 Cl3 Cl4 138.5(3) . 6_564 ?
C13 Cl3 Cl4 138.5(3) . 1_554 ?
Cl4 Cl3 C13 47.2(4) 1_554 1_554 ?
Cl4 Cl3 C13 47.2(4) 6_564 1_554 ?
Cl4 Cl3 Cl4 82.6(7) 1_554 6_564 ?
C13 Cl4 Cl3 68.7(8) . 1_556 ?
C13 Cl4 Cl3 68.7(8) . 6_566 ?
Cl3 Cl4 Cl3 0.0(8) 6_566 1_556 ?
Cl1 C14 Cl1 99.8(16) 6_565 . ?
Cl1 C14 Cl2 112.6(16) 6_565 . ?
Cl1 C14 Cl2 112.6(16) . . ?
Cl1 C14 H14 110.5 6_565 . ?
Cl1 C14 H14 110.5 . . ?
Cl2 C14 H14 110.5 . . ?

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
O2 H2 O1 0.84 1.79 2.6116(19) 164.4 7_655

_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_TBAP_4_DMA_100K_publ
_database_code_depnum_ccdc_archive 'CCDC 1919806'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;University of Liverpool
United Kingdom
;
_audit_update_record             
;
2019-05-30 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;
_audit_creation_date             2018-03-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(C4 H9 N O), C44 H26 O8'
_chemical_formula_sum            'C60 H62 N4 O12'
_chemical_formula_weight         1031.13
_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 0.0030 0.0010 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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      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                   7.1765(2)
_cell_length_b                   12.6174(4)
_cell_length_c                   14.4481(4)
_cell_angle_alpha                98.264(3)
_cell_angle_beta                 92.099(2)
_cell_angle_gamma                99.768(3)
_cell_volume                     1273.40(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    6250
_cell_measurement_temperature    100
_cell_measurement_theta_max      35.6319550913
_cell_measurement_theta_min      2.79423139784
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.994
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.993304296752
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
CCP4 7.0.048: AIMLESS, version 0.5.32 : 29/03/17
Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             546
_exptl_crystal_size_max          0.063
_exptl_crystal_size_mid          0.027
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15655
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         25.503
_diffrn_reflns_theta_min         1.383
_diffrn_ambient_temperature      100
_diffrn_detector                 PILATUS_2M_S_N_24_0107_Diamond
_diffrn_detector_area_resol_mean 'PILATUS 2M'
_diffrn_detector_type            'Photon counting pixel array'
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_radiation_collimation    '0.3 x 1.5 Double Pinhole'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_source                   Synchrotron
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3639
_reflns_number_total             4996
_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       
'DIALS 2theta refinement, DIALS 1.8.6-gc63d8697-release'
_computing_data_collection       'Diamond I19, RAL, GDA GUI'
_computing_data_reduction        
;
aimless (Evans, P. R. and Murshudov, G. N., 2013)
ccp4 (Winn, M. D. et al., 2011)
DIALS 1.8.6-gc63d8697-release (Winter, G. et al., 2018)
pointless (Evans, P., 2006)
XIA2 0.5.492-g24d9851b-dials-1.8 (Winter, G., 2010)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         4996
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0636
_refine_ls_restrained_S_all      1.044
_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)+(0.1362P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1863
_refine_ls_wR_factor_ref         0.2011
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C1(H1), C13(H13), C18(H18), C17(H17), C2(H2A), C10(H10), C21(H21),
 C20(H20), C14(H14), C11(H11)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C29(H29A,H29B,H29C), C28(H28A,H28B,
 H28C), C26(H26A,H26B,H26C), C30(H30A,H30B,H30C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_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
O6 O 1.1565(2) 1.29501(12) 0.70436(11) 0.0439(4) Uani 1 1 d . . . . .
O2 O 0.8763(2) 0.26913(13) 0.08815(11) 0.0457(4) Uani 1 1 d . . . . .
H2 H 0.9122 0.2283 0.0437 0.069 Uiso 1 1 calc GR . . . .
O3 O 0.9274(2) 1.13103(12) 0.60113(11) 0.0425(4) Uani 1 1 d . . . . .
H3 H 0.9868 1.1885 0.6331 0.064 Uiso 1 1 calc GR . . . .
O5 O 1.0309(2) 0.16007(13) -0.04075(11) 0.0476(4) Uani 1 1 d . . . . .
O4 O 0.7638(2) 1.12350(14) 0.72948(11) 0.0545(5) Uani 1 1 d . . . . .
O1 O 0.5967(2) 0.22096(16) 0.00641(11) 0.0593(5) Uani 1 1 d . . . . .
N1 N 1.0789(2) 0.02512(15) -0.15099(13) 0.0431(5) Uani 1 1 d . . . . .
N2 N 1.2501(3) 1.37271(16) 0.85226(13) 0.0512(5) Uani 1 1 d . . . . .
C4 C 0.0877(3) 0.52165(16) 0.48113(13) 0.0314(4) Uani 1 1 d . . . . .
C5 C 0.1658(3) 0.63469(16) 0.50465(14) 0.0322(4) Uani 1 1 d . . . . .
C16 C 0.4598(3) 0.78162(16) 0.51756(14) 0.0333(5) Uani 1 1 d . . . . .
C6 C 0.3498(3) 0.67279(16) 0.47650(14) 0.0332(5) Uani 1 1 d . . . . .
C3 C 0.1830(3) 0.45062(16) 0.42208(13) 0.0320(4) Uani 1 1 d . . . . .
C7 C 0.4341(3) 0.60370(16) 0.41426(14) 0.0337(5) Uani 1 1 d . . . . .
H7 H 0.5533 0.6312 0.3924 0.040 Uiso 1 1 calc R . . . .
C9 C 0.4402(3) 0.43155(16) 0.30752(14) 0.0333(5) Uani 1 1 d . . . . .
C1 C -0.0527(3) 0.29582(17) 0.44546(14) 0.0337(4) Uani 1 1 d . . . . .
H1 H -0.0947 0.2193 0.4366 0.040 Uiso 1 1 calc R . . . .
C13 C 0.7205(3) 0.38769(16) 0.23361(14) 0.0344(5) Uani 1 1 d . . . . .
H13 H 0.8544 0.3944 0.2347 0.041 Uiso 1 1 calc R . . . .
C18 C 0.6998(3) 0.93945(17) 0.50786(14) 0.0349(5) Uani 1 1 d . . . . .
H18 H 0.7883 0.9788 0.4724 0.042 Uiso 1 1 calc R . . . .
C17 C 0.5888(3) 0.84188(16) 0.46610(14) 0.0343(5) Uani 1 1 d . . . . .
H17 H 0.6005 0.8158 0.4019 0.041 Uiso 1 1 calc R . . . .
C2 C 0.1128(3) 0.33628(16) 0.41055(14) 0.0334(5) Uani 1 1 d . . . . .
H2A H 0.1837 0.2875 0.3777 0.040 Uiso 1 1 calc R . . . .
C10 C 0.3294(3) 0.36556(16) 0.23188(14) 0.0356(5) Uani 1 1 d . . . . .
H10 H 0.1953 0.3573 0.2313 0.043 Uiso 1 1 calc R . . . .
C21 C 0.4498(3) 0.82154(17) 0.61292(14) 0.0354(5) Uani 1 1 d . . . . .
H21 H 0.3682 0.7802 0.6501 0.043 Uiso 1 1 calc R . . . .
C8 C 0.3513(3) 0.49567(16) 0.38245(14) 0.0327(5) Uani 1 1 d . . . . .
C20 C 0.5563(3) 0.91945(17) 0.65322(15) 0.0363(5) Uani 1 1 d . . . . .
H20 H 0.5439 0.9462 0.7172 0.044 Uiso 1 1 calc R . . . .
C12 C 0.6086(3) 0.32259(17) 0.15869(14) 0.0352(5) Uani 1 1 d . . . . .
C14 C 0.6373(3) 0.44257(16) 0.30639(14) 0.0330(4) Uani 1 1 d . . . . .
H14 H 0.7150 0.4882 0.3561 0.040 Uiso 1 1 calc R . . . .
C22 C 0.7933(3) 1.08523(17) 0.65068(15) 0.0380(5) Uani 1 1 d . . . . .
C24 C 0.9690(3) 0.07044(19) -0.09012(15) 0.0411(5) Uani 1 1 d . . . . .
C11 C 0.4117(3) 0.31257(17) 0.15840(15) 0.0365(5) Uani 1 1 d . . . . .
H11 H 0.3344 0.2691 0.1074 0.044 Uiso 1 1 calc R . . . .
C19 C 0.6820(3) 0.97991(16) 0.60145(14) 0.0336(5) Uani 1 1 d . . . . .
C15 C 0.6917(3) 0.26534(18) 0.07669(15) 0.0404(5) Uani 1 1 d . . . . .
C27 C 1.1172(3) 1.34136(18) 0.78192(17) 0.0461(6) Uani 1 1 d . . . . .
C23 C 0.7714(3) 0.0122(2) -0.08136(18) 0.0490(6) Uani 1 1 d . . . . .
H23A H 0.7214 0.0449 -0.0239 0.073 Uiso 1 1 calc GR . . . .
H23B H 0.7733 -0.0648 -0.0787 0.073 Uiso 1 1 calc GR . . . .
H23C H 0.6904 0.0185 -0.1357 0.073 Uiso 1 1 calc GR . . . .
C25 C 1.0159(4) -0.0750(2) -0.21693(17) 0.0537(6) Uani 1 1 d . . . . .
H25A H 0.8840 -0.1046 -0.2071 0.080 Uiso 1 1 calc GR . . . .
H25B H 1.0961 -0.1283 -0.2067 0.080 Uiso 1 1 calc GR . . . .
H25C H 1.0251 -0.0591 -0.2812 0.080 Uiso 1 1 calc GR . . . .
C29 C 1.4457(3) 1.3601(2) 0.83811(19) 0.0559(7) Uani 1 1 d . . . . .
H29A H 1.4521 1.3160 0.7771 0.084 Uiso 1 1 calc GR . . . .
H29B H 1.4919 1.3241 0.8878 0.084 Uiso 1 1 calc GR . . . .
H29C H 1.5247 1.4319 0.8399 0.084 Uiso 1 1 calc GR . . . .
C28 C 0.9226(3) 1.3654(2) 0.7993(2) 0.0563(7) Uani 1 1 d . . . . .
H28A H 0.8475 1.3541 0.7395 0.084 Uiso 1 1 calc GR . . . .
H28B H 0.9324 1.4411 0.8292 0.084 Uiso 1 1 calc GR . . . .
H28C H 0.8608 1.3167 0.8404 0.084 Uiso 1 1 calc GR . . . .
C26 C 1.2701(3) 0.0797(2) -0.16050(19) 0.0559(7) Uani 1 1 d . . . . .
H26A H 1.2758 0.1091 -0.2198 0.084 Uiso 1 1 calc GR . . . .
H26B H 1.3572 0.0278 -0.1600 0.084 Uiso 1 1 calc GR . . . .
H26C H 1.3068 0.1393 -0.1082 0.084 Uiso 1 1 calc GR . . . .
C30 C 1.2122(4) 1.4253(2) 0.94582(17) 0.0636(7) Uani 1 1 d . . . . .
H30A H 1.2266 1.5040 0.9466 0.095 Uiso 1 1 calc GR . . . .
H30B H 1.3022 1.4102 0.9928 0.095 Uiso 1 1 calc GR . . . .
H30C H 1.0827 1.3966 0.9603 0.095 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
O6 C27 1.252(3) . ?
O2 H2 0.8400 . ?
O2 C15 1.321(2) . ?
O3 H3 0.8400 . ?
O3 C22 1.324(3) . ?
O5 C24 1.249(3) . ?
O4 C22 1.212(3) . ?
O1 C15 1.211(3) . ?
N1 C24 1.335(3) . ?
N1 C25 1.462(3) . ?
N1 C26 1.448(3) . ?
N2 C27 1.335(3) . ?
N2 C29 1.458(3) . ?
N2 C30 1.473(3) . ?
C4 C4 1.443(4) 2_566 ?
C4 C5 1.428(3) . ?
C4 C3 1.425(3) . ?
C5 C6 1.421(3) . ?
C5 C1 1.432(3) 2_566 ?
C16 C6 1.492(3) . ?
C16 C17 1.400(3) . ?
C16 C21 1.406(3) . ?
C6 C7 1.388(3) . ?
C3 C2 1.429(3) . ?
C3 C8 1.421(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.395(3) . ?
C9 C10 1.404(3) . ?
C9 C8 1.486(3) . ?
C9 C14 1.398(3) . ?
C1 C5 1.432(3) 2_566 ?
C1 H1 0.9500 . ?
C1 C2 1.356(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.395(3) . ?
C13 C14 1.385(3) . ?
C18 H18 0.9500 . ?
C18 C17 1.390(3) . ?
C18 C19 1.393(3) . ?
C17 H17 0.9500 . ?
C2 H2A 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.378(3) . ?
C21 H21 0.9500 . ?
C21 C20 1.375(3) . ?
C20 H20 0.9500 . ?
C20 C19 1.391(3) . ?
C12 C11 1.397(3) . ?
C12 C15 1.494(3) . ?
C14 H14 0.9500 . ?
C22 C19 1.495(3) . ?
C24 C23 1.501(3) . ?
C11 H11 0.9500 . ?
C27 C28 1.501(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 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
C15 O2 H2 109.5 . . ?
C22 O3 H3 109.5 . . ?
C24 N1 C25 124.43(19) . . ?
C24 N1 C26 120.27(19) . . ?
C26 N1 C25 115.12(18) . . ?
C27 N2 C29 120.5(2) . . ?
C27 N2 C30 123.2(2) . . ?
C29 N2 C30 116.2(2) . . ?
C5 C4 C4 119.8(2) . 2_566 ?
C3 C4 C4 119.6(2) . 2_566 ?
C3 C4 C5 120.64(17) . . ?
C4 C5 C1 117.93(17) . 2_566 ?
C6 C5 C4 118.69(18) . . ?
C6 C5 C1 123.37(18) . 2_566 ?
C17 C16 C6 121.77(18) . . ?
C17 C16 C21 117.96(18) . . ?
C21 C16 C6 119.98(18) . . ?
C5 C6 C16 121.64(17) . . ?
C7 C6 C5 118.94(18) . . ?
C7 C6 C16 119.26(17) . . ?
C4 C3 C2 118.49(17) . . ?
C8 C3 C4 118.65(18) . . ?
C8 C3 C2 122.71(18) . . ?
C6 C7 H7 118.6 . . ?
C6 C7 C8 122.86(17) . . ?
C8 C7 H7 118.6 . . ?
C10 C9 C8 120.80(17) . . ?
C14 C9 C10 118.21(18) . . ?
C14 C9 C8 120.76(18) . . ?
C5 C1 H1 119.1 2_566 . ?
C2 C1 C5 121.79(19) . 2_566 ?
C2 C1 H1 119.1 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C14 C13 C12 120.39(17) . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.39(18) . . ?
C19 C18 H18 119.8 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.75(19) . . ?
C18 C17 H17 119.6 . . ?
C3 C2 H2A 119.3 . . ?
C1 C2 C3 121.47(18) . . ?
C1 C2 H2A 119.3 . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.16(17) . . ?
C11 C10 H10 119.4 . . ?
C16 C21 H21 119.5 . . ?
C20 C21 C16 120.99(19) . . ?
C20 C21 H21 119.5 . . ?
C3 C8 C9 121.95(17) . . ?
C7 C8 C3 118.91(18) . . ?
C7 C8 C9 119.13(17) . . ?
C21 C20 H20 119.6 . . ?
C21 C20 C19 120.80(19) . . ?
C19 C20 H20 119.6 . . ?
C13 C12 C11 119.23(18) . . ?
C13 C12 C15 122.45(17) . . ?
C11 C12 C15 118.30(19) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.79(18) . . ?
C13 C14 H14 119.6 . . ?
O3 C22 C19 113.99(18) . . ?
O4 C22 O3 123.62(19) . . ?
O4 C22 C19 122.38(19) . . ?
O5 C24 N1 120.12(19) . . ?
O5 C24 C23 120.56(19) . . ?
N1 C24 C23 119.3(2) . . ?
C10 C11 C12 120.19(19) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C18 C19 C22 123.54(18) . . ?
C20 C19 C18 119.02(19) . . ?
C20 C19 C22 117.43(18) . . ?
O2 C15 C12 113.77(18) . . ?
O1 C15 O2 123.93(19) . . ?
O1 C15 C12 122.29(19) . . ?
O6 C27 N2 120.5(2) . . ?
O6 C27 C28 122.0(2) . . ?
N2 C27 C28 117.6(2) . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N1 C25 H25A 109.5 . . ?
N1 C25 H25B 109.5 . . ?
N1 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N2 C29 H29A 109.5 . . ?
N2 C29 H29B 109.5 . . ?
N2 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N1 C26 H26A 109.5 . . ?
N1 C26 H26B 109.5 . . ?
N1 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N2 C30 H30A 109.5 . . ?
N2 C30 H30B 109.5 . . ?
N2 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

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
O2 H2 O5 0.84 1.73 2.554(2) 168.3 .
O3 H3 O6 0.84 1.82 2.644(2) 167.3 .

_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_TBAP_C2c_Desolvated_Structure_300K_publ
_database_code_depnum_ccdc_archive 'CCDC 1919809'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;University of Liverpool
United Kingdom
;
_audit_update_record             
;
2019-05-30 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT027_ck_tbap_ace_300k    
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ...... 25.00 Degree
RESPONSE: The crystal was weakly diffracting at high angle and a suitable
resolution limit was applied during refinement.  
;
_vrf_PLAT602_ck_tbap_ace_300k    
;
PROBLEM: VERY LARGE Solvent Accessible VOID(S) in Structure ! Info
RESPONSE: The crystal structure contains large 1D voids that 
did not contain any ordered electron density. No solvent mask was applied 
during refinement.
;
_vrf_PLAT049_ck_tbap_ace_300k    
;
PROBLEM: Calculated Density Less Than 1.0 gcm-3 ......... 0.6940 Check
RESPONSE: The crystal structure contains large 1D voids that 
did not contain any ordered electron density. No solvent mask was applied 
during refinement. 
;
# end Validation Reply Form

_audit_creation_date             2018-03-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H26 O8'
_chemical_formula_sum            'C44 H26 O8'
_chemical_formula_weight         682.65
_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 0.0040 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0130 0.0070 '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'

_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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   29.09(4)
_cell_length_b                   28.61(4)
_cell_length_c                   3.928(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.87(2)
_cell_angle_gamma                90
_cell_volume                     3268(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8473
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      43.537
_cell_measurement_theta_min      3.231
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.057
_exptl_absorpt_correction_T_max  0.8630
_exptl_absorpt_correction_T_min  0.7555
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1397 before and 0.0481 after correction.
The Ratio of minimum to maximum transmission is 0.8754.
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    0.694
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            11570
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.997
_diffrn_reflns_theta_min         1.527
_diffrn_ambient_temperature      300.15
_diffrn_detector_area_resol_mean 10.42
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker D8 with PHOTON II detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_wavelength     0.7749
_diffrn_source                   'Advanced Light Source, station 11.3.1'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2583
_reflns_number_total             3061
_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 (?, 2016)'
_computing_data_collection       'Bruker APEX3 Bruker-AXS, Madison WI'
_computing_data_reduction        'SAINT V8.38A (Bruker-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT 2014/4 Bruker-AXS, Madison WI'
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         3061
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0481
_refine_ls_restrained_S_all      1.079
_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)+(0.0880P)²+0.5740P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1421
_refine_ls_wR_factor_ref         0.1482
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C11(H11)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.26317(4) 0.69916(4) 0.2800(4) 0.0843(4) Uani 1 1 d . . . . .
H1 H 0.2434 0.7180 0.3322 0.101 Uiso 1 1 calc GR . . . .
C1 C 0.30223(5) 0.71361(5) 0.3850(4) 0.0563(4) Uani 1 1 d . . . . .
O2 O 0.30848(4) 0.75057(4) 0.5536(3) 0.0803(4) Uani 1 1 d . . . . .
C2 C 0.34286(4) 0.68436(4) 0.3072(3) 0.0476(3) Uani 1 1 d . . . . .
C3 C 0.38645(4) 0.69828(4) 0.4176(3) 0.0493(3) Uani 1 1 d . . . . .
H3 H 0.3904 0.7264 0.5336 0.059 Uiso 1 1 calc R . . . .
C4 C 0.42421(4) 0.67032(4) 0.3554(3) 0.0441(3) Uani 1 1 d . . . . .
H4 H 0.4533 0.6799 0.4313 0.053 Uiso 1 1 calc R . . . .
C5 C 0.41918(4) 0.62815(4) 0.1812(3) 0.0370(3) Uani 1 1 d . . . . .
C6 C 0.37523(4) 0.61506(4) 0.0643(3) 0.0430(3) Uani 1 1 d . . . . .
H6 H 0.3713 0.5874 -0.0580 0.052 Uiso 1 1 calc R . . . .
C7 C 0.33739(4) 0.64279(4) 0.1286(3) 0.0481(3) Uani 1 1 d . . . . .
H7 H 0.3082 0.6335 0.0516 0.058 Uiso 1 1 calc R . . . .
C8 C 0.42528(3) 0.52350(4) 0.2710(3) 0.0362(3) Uani 1 1 d . . . . .
H8 H 0.4013 0.5393 0.3716 0.043 Uiso 1 1 calc R . . . .
C9 C 0.46120(3) 0.55003(4) 0.1206(3) 0.0327(3) Uani 1 1 d . . . . .
C10 C 0.46053(3) 0.59948(4) 0.1015(3) 0.0351(3) Uani 1 1 d . . . . .
C11 C 0.5000 0.62248(5) 0.0000 0.0375(4) Uani 1 2 d S T P . .
H11 H 0.5000 0.6550 0.0000 0.045 Uiso 1 2 calc RS T P . .
C12 C 0.5000 0.52513(5) 0.0000 0.0313(3) Uani 1 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
O1 H1 0.8200 . ?
O1 C1 1.266(2) . ?
C1 O2 1.258(2) . ?
C1 C2 1.488(2) . ?
C2 C3 1.385(2) . ?
C2 C7 1.387(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.387(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.393(2) . ?
C5 C6 1.396(2) . ?
C5 C10 1.497(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.387(2) . ?
C7 H7 0.9300 . ?
C8 C8 1.345(3) 6_565 ?
C8 H8 0.9300 . ?
C8 C9 1.4343(19) . ?
C9 C10 1.417(2) . ?
C9 C12 1.4287(18) . ?
C10 C11 1.3929(19) . ?
C11 C10 1.3928(19) 2_655 ?
C11 H11 0.9300 . ?
C12 C9 1.4288(18) 2_655 ?
C12 C12 1.438(3) 5_665 ?

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 O1 H1 109.5 . . ?
O1 C1 C2 117.38(15) . . ?
O2 C1 O1 123.98(12) . . ?
O2 C1 C2 118.62(14) . . ?
C3 C2 C1 119.94(14) . . ?
C3 C2 C7 119.57(11) . . ?
C7 C2 C1 120.48(14) . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.09(14) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.01(13) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 118.33(10) . . ?
C4 C5 C10 120.35(12) . . ?
C6 C5 C10 121.19(13) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.72(14) . . ?
C7 C6 H6 119.6 . . ?
C2 C7 H7 119.9 . . ?
C6 C7 C2 120.25(13) . . ?
C6 C7 H7 119.9 . . ?
C8 C8 H8 119.0 6_565 . ?
C8 C8 C9 121.94(7) 6_565 . ?
C9 C8 H8 119.0 . . ?
C10 C9 C8 122.76(10) . . ?
C10 C9 C12 119.34(10) . . ?
C12 C9 C8 117.84(13) . . ?
C9 C10 C5 123.06(10) . . ?
C11 C10 C5 118.46(13) . . ?
C11 C10 C9 118.48(10) . . ?
C10 C11 C10 123.63(16) 2_655 . ?
C10 C11 H11 118.2 2_655 . ?
C10 C11 H11 118.2 . . ?
C9 C12 C9 120.18(16) . 2_655 ?
C9 C12 C12 119.91(8) . 5_665 ?
C9 C12 C12 119.91(8) 2_655 5_665 ?

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
O1 H1 O2 0.82 1.82 2.633(3) 168.1 7_566

_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_TBAP_P-1_4_NMP_100K
_database_code_depnum_ccdc_archive 'CCDC 1919808'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;University of Liverpool
United Kingdom
;
_audit_update_record             
;
2019-05-30 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_THETM01_TBAP_P-1_4_NMP_100K 
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: The crystal was weakly diffracting at high angle and a
suitable resolution limit was applied during refinement.
;
# end Validation Reply Form

_audit_creation_date             2018-03-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H26 O8, 4(C5 H9 N O)'
_chemical_formula_sum            'C64 H62 N4 O12'
_chemical_formula_weight         1079.17
_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 0.0030 0.0010 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0100 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      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                   7.2283(3)
_cell_length_b                   13.0283(6)
_cell_length_c                   14.3638(7)
_cell_angle_alpha                99.572(4)
_cell_angle_beta                 91.962(4)
_cell_angle_gamma                100.785(4)
_cell_volume                     1307.30(11)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2418
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.5697597366
_cell_measurement_theta_min      1.9008910816
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.994
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.993403237634
_exptl_absorpt_correction_type   empirical
_exptl.absorpt_process_details   
;
CCP4 7.0.048: AIMLESS, version 0.5.32 : 29/03/17
Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;

_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             570
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0988
_diffrn_reflns_av_unetI/netI     0.1001
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13145
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        22.502
_diffrn_reflns_theta_max         22.502
_diffrn_reflns_theta_min         1.397
_diffrn_ambient_temperature      100
_diffrn_detector                 'Photon counting pixel array'
_diffrn_detector_area_resol_mean 'Pilatus 2M'
_diffrn_detector_type            PILATUS_2M_S_N_24_0107_Diamond
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_radiation_collimation    '0.3 x 1.5 Double Pinhole'
_diffrn_radiation_monochromator  'silicon 111'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.6889
_diffrn_source                   Synchrotron
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2466
_reflns_number_total             3665
_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       
'DIALS 2theta refinement, DIALS 1.8.6-gc63d8697-release'
_computing_data_collection       'i19 Diamond Light Source, RAL, UK, GDA GUI'
_computing_data_reduction        
;
aimless (Evans, P. R. and Murshudov, G. N., 2013)
ccp4 (Winn, M. D. et al., 2011)
DIALS 1.8.6-gc63d8697-release (Winter, G. et al., 2018)
pointless (Evans, P., 2006)
XIA2 0.5.492-g24d9851b-dials-1.8 (Winter, G., 2010)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_refine_diff_density_max         0.767
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     365
_refine_ls_number_reflns         3665
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1137
_refine_ls_R_factor_gt           0.0835
_refine_ls_restrained_S_all      1.069
_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)+(0.1601P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2200
_refine_ls_wR_factor_ref         0.2516
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C28(H28A,H28B), C29(H29A,
 H29B), C30(H30A,H30B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C5(H5), C10(H10), C11(H11), C13(H13), C14(H14), C17(H17),
 C18(H18), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C32(H32A,H32B,H32C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_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 0.1885(4) -0.1113(2) 0.2766(2) 0.0594(9) Uani 1 1 d . . . . .
O2 O 0.0828(4) -0.1266(2) 0.4200(2) 0.0514(8) Uani 1 1 d . . . . .
H2 H 0.0152 -0.1825 0.3896 0.077 Uiso 1 1 calc GR . . . .
O3 O 0.1286(4) 0.7245(2) 0.9150(2) 0.0493(8) Uani 1 1 d . . . . .
H3 H 0.0888 0.7554 0.9641 0.074 Uiso 1 1 calc GR . . . .
O4 O 0.4092(4) 0.7863(2) 0.9957(2) 0.0570(9) Uani 1 1 d . . . . .
O5 O 0.1602(4) 0.2879(2) 0.6818(2) 0.0501(8) Uani 1 1 d . . . . .
O6 O 0.0528(4) 0.1824(2) 0.9559(2) 0.0497(8) Uani 1 1 d . . . . .
N1 N 0.1995(5) 0.3697(3) 0.8357(3) 0.0573(10) Uani 1 1 d . . . . .
N2 N -0.0628(5) 0.0087(3) 0.8879(3) 0.0608(11) Uani 1 1 d . . . . .
C1 C 1.1055(5) 0.3408(3) 0.4043(3) 0.0405(10) Uani 1 1 d . . . . .
H1 H 1.1735 0.2938 0.3689 0.049 Uiso 1 1 calc R . . . .
C2 C 0.9406(5) 0.3011(3) 0.4395(3) 0.0415(10) Uani 1 1 d . . . . .
H2A H 0.8956 0.2265 0.4281 0.050 Uiso 1 1 calc R . . . .
C3 C 0.8326(5) 0.3685(3) 0.4931(3) 0.0400(10) Uani 1 1 d . . . . .
C4 C 0.6498(5) 0.3302(3) 0.5232(3) 0.0386(9) Uani 1 1 d . . . . .
C5 C 0.5686(5) 0.3967(3) 0.5862(3) 0.0408(10) Uani 1 1 d . . . . .
H5 H 0.4506 0.3690 0.6085 0.049 Uiso 1 1 calc R . . . .
C6 C 0.6511(5) 0.5040(3) 0.6195(3) 0.0403(10) Uani 1 1 d . . . . .
C7 C 0.8219(5) 0.5474(3) 0.5799(3) 0.0399(10) Uani 1 1 d . . . . .
C8 C 0.9119(5) 0.4792(3) 0.5193(3) 0.0382(9) Uani 1 1 d . . . . .
C9 C 0.5388(5) 0.2218(3) 0.4839(3) 0.0440(10) Uani 1 1 d . . . . .
C10 C 0.5345(5) 0.1806(3) 0.3872(3) 0.0450(10) Uani 1 1 d . . . . .
H10 H 0.6085 0.2201 0.3470 0.054 Uiso 1 1 calc R . . . .
C11 C 0.4234(5) 0.0829(3) 0.3498(3) 0.0454(10) Uani 1 1 d . . . . .
H11 H 0.4247 0.0551 0.2844 0.054 Uiso 1 1 calc R . . . .
C12 C 0.3099(5) 0.0250(3) 0.4068(3) 0.0434(10) Uani 1 1 d . . . . .
C13 C 0.3126(5) 0.0655(3) 0.5026(3) 0.0435(10) Uani 1 1 d . . . . .
H13 H 0.2359 0.0265 0.5422 0.052 Uiso 1 1 calc R . . . .
C14 C 0.4266(5) 0.1628(3) 0.5410(3) 0.0450(10) Uani 1 1 d . . . . .
H14 H 0.4279 0.1894 0.6068 0.054 Uiso 1 1 calc R . . . .
C15 C 0.1902(6) -0.0771(3) 0.3610(3) 0.0468(11) Uani 1 1 d . . . . .
C16 C 0.5651(5) 0.5658(3) 0.6962(3) 0.0413(10) Uani 1 1 d . . . . .
C17 C 0.3692(5) 0.5588(3) 0.6949(3) 0.0424(10) Uani 1 1 d . . . . .
H17 H 0.2914 0.5158 0.6429 0.051 Uiso 1 1 calc R . . . .
C18 C 0.2870(5) 0.6134(3) 0.7677(3) 0.0406(10) Uani 1 1 d . . . . .
H18 H 0.1542 0.6089 0.7646 0.049 Uiso 1 1 calc R . . . .
C19 C 0.3975(5) 0.6748(3) 0.8455(3) 0.0418(10) Uani 1 1 d . . . . .
C20 C 0.5922(5) 0.6805(3) 0.8490(3) 0.0445(10) Uani 1 1 d . . . . .
H20 H 0.6685 0.7213 0.9024 0.053 Uiso 1 1 calc R . . . .
C21 C 0.6750(5) 0.6279(3) 0.7760(3) 0.0457(10) Uani 1 1 d . . . . .
H21 H 0.8081 0.6334 0.7793 0.055 Uiso 1 1 calc R . . . .
C22 C 0.3148(5) 0.7342(3) 0.9264(3) 0.0456(10) Uani 1 1 d . . . . .
C23 C 0.0583(6) 0.0988(4) 0.9007(3) 0.0547(12) Uani 1 1 d . . . . .
C24 C 0.2251(7) 0.0842(4) 0.8368(3) 0.0592(12) Uani 1 1 d . . . . .
H24A H 0.2236 0.1240 0.7839 0.071 Uiso 1 1 calc R . . . .
H24B H 0.3481 0.1083 0.8738 0.071 Uiso 1 1 calc R . . . .
C25 C 0.1888(7) -0.0336(4) 0.8009(4) 0.0665(14) Uani 1 1 d . . . . .
H25A H 0.2689 -0.0685 0.8378 0.080 Uiso 1 1 calc R . . . .
H25B H 0.2155 -0.0487 0.7333 0.080 Uiso 1 1 calc R . . . .
C26 C -0.0186(6) -0.0724(3) 0.8136(3) 0.0563(12) Uani 1 1 d . . . . .
H26A H -0.0964 -0.0775 0.7543 0.068 Uiso 1 1 calc R . . . .
H26B H -0.0397 -0.1427 0.8334 0.068 Uiso 1 1 calc R . . . .
C27 C -0.2462(6) 0.0010(4) 0.9245(3) 0.0610(12) Uani 1 1 d . . . . .
H27A H -0.2364 0.0460 0.9871 0.091 Uiso 1 1 calc GR . . . .
H27B H -0.2964 -0.0729 0.9300 0.091 Uiso 1 1 calc GR . . . .
H27C H -0.3311 0.0246 0.8815 0.091 Uiso 1 1 calc GR . . . .
C28 C 0.1025(6) 0.4229(3) 0.9106(3) 0.0539(12) Uani 1 1 d . . . . .
H28A H 0.1507 0.5005 0.9230 0.065 Uiso 1 1 calc R . . . .
H28B H 0.1151 0.3949 0.9700 0.065 Uiso 1 1 calc R . . . .
C29 C -0.1057(6) 0.3949(4) 0.8679(3) 0.0649(13) Uani 1 1 d . . . . .
H29A H -0.1792 0.3357 0.8944 0.078 Uiso 1 1 calc R . . . .
H29B H -0.1672 0.4571 0.8813 0.078 Uiso 1 1 calc R . . . .
C30 C -0.0922(6) 0.3633(4) 0.7641(4) 0.0575(12) Uani 1 1 d . . . . .
H30A H -0.1034 0.4228 0.7308 0.069 Uiso 1 1 calc R . . . .
H30B H -0.1930 0.3017 0.7377 0.069 Uiso 1 1 calc R . . . .
C31 C 0.1015(6) 0.3345(3) 0.7541(3) 0.0530(11) Uani 1 1 d . . . . .
C32 C 0.3987(6) 0.3669(4) 0.8508(4) 0.0584(12) Uani 1 1 d . . . . .
H32A H 0.4723 0.4395 0.8645 0.088 Uiso 1 1 calc GR . . . .
H32B H 0.4416 0.3282 0.7937 0.088 Uiso 1 1 calc GR . . . .
H32C H 0.4163 0.3310 0.9043 0.088 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 C15 1.219(5) . ?
O2 H2 0.8400 . ?
O2 C15 1.332(5) . ?
O3 H3 0.8400 . ?
O3 C22 1.330(5) . ?
O4 C22 1.213(5) . ?
O5 C31 1.243(5) . ?
O6 C23 1.243(5) . ?
N1 C28 1.455(5) . ?
N1 C31 1.315(6) . ?
N1 C32 1.457(5) . ?
N2 C23 1.308(6) . ?
N2 C26 1.461(5) . ?
N2 C27 1.435(6) . ?
C1 H1 0.9500 . ?
C1 C2 1.356(5) . ?
C1 C7 1.430(5) 2_766 ?
C2 H2A 0.9500 . ?
C2 C3 1.431(5) . ?
C3 C4 1.430(5) . ?
C3 C8 1.430(5) . ?
C4 C5 1.371(5) . ?
C4 C9 1.496(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.409(5) . ?
C6 C7 1.435(5) . ?
C6 C16 1.479(5) . ?
C7 C1 1.430(5) 2_766 ?
C7 C8 1.404(6) . ?
C8 C8 1.454(8) 2_766 ?
C9 C10 1.400(6) . ?
C9 C14 1.393(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.390(6) . ?
C12 C13 1.387(6) . ?
C12 C15 1.480(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.392(5) . ?
C14 H14 0.9500 . ?
C16 C17 1.401(5) . ?
C16 C21 1.410(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.381(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.388(5) . ?
C19 C20 1.394(5) . ?
C19 C22 1.493(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.373(5) . ?
C21 H21 0.9500 . ?
C23 C24 1.561(7) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.506(6) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.518(6) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.560(6) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.490(7) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C31 1.521(6) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 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
C15 O2 H2 109.5 . . ?
C22 O3 H3 109.5 . . ?
C28 N1 C32 120.0(4) . . ?
C31 N1 C28 115.9(4) . . ?
C31 N1 C32 123.8(4) . . ?
C23 N2 C26 114.2(4) . . ?
C23 N2 C27 121.5(4) . . ?
C27 N2 C26 122.1(4) . . ?
C2 C1 H1 119.6 . . ?
C2 C1 C7 120.7(4) . 2_766 ?
C7 C1 H1 119.6 2_766 . ?
C1 C2 H2A 119.1 . . ?
C1 C2 C3 121.8(4) . . ?
C3 C2 H2A 119.1 . . ?
C4 C3 C2 123.1(3) . . ?
C8 C3 C2 118.6(3) . . ?
C8 C3 C4 118.3(3) . . ?
C3 C4 C9 122.1(3) . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 C9 118.6(3) . . ?
C4 C5 H5 118.3 . . ?
C4 C5 C6 123.4(3) . . ?
C6 C5 H5 118.3 . . ?
C5 C6 C7 118.0(3) . . ?
C5 C6 C16 119.4(3) . . ?
C7 C6 C16 122.6(3) . . ?
C1 C7 C6 121.4(4) 2_766 . ?
C8 C7 C1 119.4(3) . 2_766 ?
C8 C7 C6 119.0(3) . . ?
C3 C8 C8 118.6(4) . 2_766 ?
C7 C8 C3 121.3(3) . . ?
C7 C8 C8 120.0(4) . 2_766 ?
C10 C9 C4 120.5(4) . . ?
C14 C9 C4 120.9(4) . . ?
C14 C9 C10 118.5(4) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.6(4) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.7(4) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C15 117.6(4) . . ?
C13 C12 C11 119.0(4) . . ?
C13 C12 C15 123.4(4) . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.5(4) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.6(4) . . ?
C13 C14 H14 119.7 . . ?
O1 C15 O2 123.5(4) . . ?
O1 C15 C12 122.6(4) . . ?
O2 C15 C12 113.9(4) . . ?
C17 C16 C6 120.8(3) . . ?
C17 C16 C21 117.6(4) . . ?
C21 C16 C6 121.4(3) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.2(4) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C20 119.1(4) . . ?
C18 C19 C22 122.3(3) . . ?
C20 C19 C22 118.6(3) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.8(4) . . ?
C21 C20 H20 119.6 . . ?
C16 C21 H21 119.6 . . ?
C20 C21 C16 120.8(4) . . ?
C20 C21 H21 119.6 . . ?
O3 C22 C19 113.5(4) . . ?
O4 C22 O3 123.5(4) . . ?
O4 C22 C19 122.9(4) . . ?
O6 C23 N2 128.3(4) . . ?
O6 C23 C24 123.6(4) . . ?
N2 C23 C24 108.1(4) . . ?
C23 C24 H24A 111.1 . . ?
C23 C24 H24B 111.1 . . ?
H24A C24 H24B 109.0 . . ?
C25 C24 C23 103.5(4) . . ?
C25 C24 H24A 111.1 . . ?
C25 C24 H24B 111.1 . . ?
C24 C25 H25A 110.7 . . ?
C24 C25 H25B 110.7 . . ?
C24 C25 C26 105.2(4) . . ?
H25A C25 H25B 108.8 . . ?
C26 C25 H25A 110.7 . . ?
C26 C25 H25B 110.7 . . ?
N2 C26 C25 103.6(3) . . ?
N2 C26 H26A 111.0 . . ?
N2 C26 H26B 111.0 . . ?
C25 C26 H26A 111.0 . . ?
C25 C26 H26B 111.0 . . ?
H26A C26 H26B 109.0 . . ?
N2 C27 H27A 109.5 . . ?
N2 C27 H27B 109.5 . . ?
N2 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N1 C28 H28A 111.4 . . ?
N1 C28 H28B 111.4 . . ?
N1 C28 C29 101.8(3) . . ?
H28A C28 H28B 109.3 . . ?
C29 C28 H28A 111.4 . . ?
C29 C28 H28B 111.4 . . ?
C28 C29 H29A 110.7 . . ?
C28 C29 H29B 110.7 . . ?
H29A C29 H29B 108.8 . . ?
C30 C29 C28 105.0(4) . . ?
C30 C29 H29A 110.7 . . ?
C30 C29 H29B 110.7 . . ?
C29 C30 H30A 110.7 . . ?
C29 C30 H30B 110.7 . . ?
C29 C30 C31 105.0(4) . . ?
H30A C30 H30B 108.8 . . ?
C31 C30 H30A 110.7 . . ?
C31 C30 H30B 110.7 . . ?
O5 C31 N1 125.3(4) . . ?
O5 C31 C30 126.8(4) . . ?
N1 C31 C30 107.9(4) . . ?
N1 C32 H32A 109.5 . . ?
N1 C32 H32B 109.5 . . ?
N1 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

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
O2 H2 O5 0.84 1.83 2.657(4) 169.5 2_556
O3 H3 O6 0.84 1.76 2.577(4) 163.1 2_567

_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_Ph4Py
_database_code_depnum_ccdc_archive 'CCDC 1919803'
loop_
_audit_author_name
_audit_author_address
'Marc Little'
;University of Liverpool
United Kingdom
;
_audit_update_record             
;
2019-05-30 deposited with the CCDC.	2020-03-16 downloaded from the CCDC.
;


# start Validation Reply Form
_vrf_THETM01_Ph4Py               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The crystal was poorly diffracting at higher angle.
;
_vrf_PLAT089_Ph4Py               
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........
RESPONSE: The crystal was poorly diffracting at higher angle.
;
# end Validation Reply Form


_audit_creation_method           'XIA2 0.5.474-gb1e580cd-dials-1.8'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H26'
_chemical_formula_sum            'C40 H26'
_chemical_formula_weight         506.61


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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   11.30460(10)
_cell_length_b                   12.38000(10)
_cell_length_c                   19.03532(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2664.01(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6381
_cell_measurement_theta_min      3.80
_cell_measurement_theta_max      49.24

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CCP4 7.0.046: AIMLESS, version 0.5.32 : 29/03/17
Scaling & analysis of unmerged intensities, absorption correction using spherical harmonics
;

_exptl_special_details           ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.6889
_diffrn_detector                 'Photon counting pixel array'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'Diamond Light Source Beamline I19-1'
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10190
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.031
_diffrn_reflns_theta_max         21.731
_diffrn_reflns_theta_full        21.731
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             3398
_reflns_number_gt                3078
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_max     0.968
_reflns_Friedel_fraction_full    0.968

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       
'DIALS 2theta refinement, DIALS 1.8.1-g1afca60c-release-hotfix1'
_computing_data_reduction        
;
aimless (Evans, P. R. and Murshudov, G. N., 2013)
ccp4 (Winn, M. D. et al., 2011)
DIALS 1.8.1-g1afca60c-release-hotfix1
pointless (Evans, P., 2006)
XIA2 0.5.474-gb1e580cd-dials-1.8 (Winter, G., 2010)
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0503P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1248 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -5.9(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3398
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0787
_refine_ls_wR_factor_gt          0.0769
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_restrained_S_all      0.978
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0225(3) 0.5599(2) 0.61124(16) 0.0289(7) Uani 1 1 d . . . . .
H1 H 0.0688 0.5989 0.6442 0.035 Uiso 1 1 calc R U . . .
C2 C -0.0925(3) 0.5927(3) 0.59684(17) 0.0334(8) Uani 1 1 d . . . . .
H2 H -0.1237 0.6555 0.6188 0.040 Uiso 1 1 calc R U . . .
C3 C -0.1609(3) 0.5345(3) 0.55085(16) 0.0354(8) Uani 1 1 d . . . . .
H3 H -0.2395 0.5568 0.5408 0.042 Uiso 1 1 calc R U . . .
C4 C -0.1150(3) 0.4434(3) 0.51935(16) 0.0361(8) Uani 1 1 d . . . . .
H4 H -0.1627 0.4020 0.4883 0.043 Uiso 1 1 calc R U . . .
C5 C 0.0017(3) 0.4115(3) 0.53283(15) 0.0307(7) Uani 1 1 d . . . . .
H5 H 0.0327 0.3489 0.5106 0.037 Uiso 1 1 calc R U . . .
C6 C 0.0706(2) 0.4692(2) 0.57735(15) 0.0219(7) Uani 1 1 d . . . . .
C7 C 0.1996(2) 0.4424(2) 0.59164(14) 0.0229(7) Uani 1 1 d . . . . .
C8 C 0.2828(3) 0.5236(2) 0.58414(14) 0.0243(7) Uani 1 1 d . . . . .
H8 H 0.2564 0.5929 0.5696 0.029 Uiso 1 1 calc R U . . .
C9 C 0.4024(2) 0.5094(2) 0.59668(14) 0.0211(7) Uani 1 1 d . . . . .
C10 C 0.4848(2) 0.6040(2) 0.59310(15) 0.0218(7) Uani 1 1 d . . . . .
C11 C 0.4932(3) 0.6674(2) 0.53374(16) 0.0277(7) Uani 1 1 d . . . . .
H11 H 0.4457 0.6513 0.4939 0.033 Uiso 1 1 calc R U . . .
C12 C 0.5707(3) 0.7550(2) 0.53173(17) 0.0337(8) Uani 1 1 d . . . . .
H12 H 0.5769 0.7971 0.4902 0.040 Uiso 1 1 calc R U . . .
C13 C 0.6385(3) 0.7808(2) 0.58952(17) 0.0294(7) Uani 1 1 d . . . . .
H13 H 0.6914 0.8403 0.5878 0.035 Uiso 1 1 calc R U . . .
C14 C 0.6290(3) 0.7193(2) 0.65005(16) 0.0261(7) Uani 1 1 d . . . . .
H14 H 0.6745 0.7373 0.6903 0.031 Uiso 1 1 calc R U . . .
C15 C 0.5530(2) 0.6318(2) 0.65183(16) 0.0256(7) Uani 1 1 d . . . . .
H15 H 0.5470 0.5899 0.6935 0.031 Uiso 1 1 calc R U . . .
C16 C 0.4445(2) 0.4043(2) 0.61354(14) 0.0218(7) Uani 1 1 d . . . . .
C17 C 0.5673(2) 0.3803(2) 0.62008(15) 0.0240(7) Uani 1 1 d . . . . .
H17 H 0.6234 0.4369 0.6149 0.029 Uiso 1 1 calc R U . . .
C18 C 0.6060(3) 0.2790(2) 0.63344(15) 0.0238(7) Uani 1 1 d . . . . .
H18 H 0.6887 0.2660 0.6355 0.029 Uiso 1 1 calc R U . . .
C19 C 0.5268(2) 0.1914(2) 0.64448(14) 0.0219(7) Uani 1 1 d . . . . .
C20 C 0.4021(3) 0.2129(2) 0.64189(14) 0.0211(7) Uani 1 1 d . . . . .
C21 C 0.3612(3) 0.3191(2) 0.62271(14) 0.0215(7) Uani 1 1 d . . . . .
C22 C 0.2376(2) 0.3384(2) 0.61337(14) 0.0213(7) Uani 1 1 d . . . . .
C23 C 0.1570(3) 0.2515(2) 0.62746(14) 0.0238(7) Uani 1 1 d . . . . .
H23 H 0.0745 0.2631 0.6215 0.029 Uiso 1 1 calc R U . . .
C24 C 0.1956(2) 0.1533(2) 0.64902(14) 0.0224(7) Uani 1 1 d . . . . .
H24 H 0.1393 0.0985 0.6591 0.027 Uiso 1 1 calc R U . . .
C25 C 0.3188(2) 0.1298(2) 0.65703(14) 0.0219(7) Uani 1 1 d . . . . .
C26 C 0.3604(2) 0.0265(2) 0.67694(14) 0.0213(7) Uani 1 1 d . . . . .
C27 C 0.2816(2) -0.0634(2) 0.70060(14) 0.0216(7) Uani 1 1 d . . . . .
C28 C 0.1986(2) -0.0460(2) 0.75359(15) 0.0241(7) Uani 1 1 d . . . . .
H28 H 0.1882 0.0246 0.7720 0.029 Uiso 1 1 calc R U . . .
C29 C 0.1312(2) -0.1303(2) 0.77973(15) 0.0248(7) Uani 1 1 d . . . . .
H29 H 0.0739 -0.1172 0.8152 0.030 Uiso 1 1 calc R U . . .
C30 C 0.1477(3) -0.2346(2) 0.75384(15) 0.0276(7) Uani 1 1 d . . . . .
H30 H 0.1014 -0.2929 0.7711 0.033 Uiso 1 1 calc R U . . .
C31 C 0.2326(2) -0.2521(2) 0.70248(15) 0.0289(7) Uani 1 1 d . . . . .
H31 H 0.2458 -0.3233 0.6855 0.035 Uiso 1 1 calc R U . . .
C32 C 0.2981(3) -0.1679(2) 0.67576(15) 0.0278(7) Uani 1 1 d . . . . .
H32 H 0.3550 -0.1813 0.6401 0.033 Uiso 1 1 calc R U . . .
C33 C 0.4818(3) 0.0063(2) 0.67523(14) 0.0233(7) Uani 1 1 d . . . . .
H33 H 0.5087 -0.0645 0.6858 0.028 Uiso 1 1 calc R U . . .
C34 C 0.5653(2) 0.0850(2) 0.65873(14) 0.0211(6) Uani 1 1 d . . . . .
C35 C 0.6939(2) 0.0517(2) 0.65731(14) 0.0207(7) Uani 1 1 d . . . . .
C36 C 0.7379(2) -0.0113(2) 0.71124(16) 0.0250(7) Uani 1 1 d . . . . .
H36 H 0.6896 -0.0270 0.7508 0.030 Uiso 1 1 calc R U . . .
C37 C 0.8519(3) -0.0517(2) 0.70789(16) 0.0265(7) Uani 1 1 d . . . . .
H37 H 0.8812 -0.0955 0.7450 0.032 Uiso 1 1 calc R U . . .
C38 C 0.9235(3) -0.0286(2) 0.65069(16) 0.0270(7) Uani 1 1 d . . . . .
H38 H 1.0015 -0.0569 0.6482 0.032 Uiso 1 1 calc R U . . .
C39 C 0.8805(3) 0.0363(2) 0.59710(16) 0.0275(7) Uani 1 1 d . . . . .
H39 H 0.9297 0.0541 0.5583 0.033 Uiso 1 1 calc R U . . .
C40 C 0.7649(2) 0.0755(2) 0.60015(15) 0.0259(7) Uani 1 1 d . . . . .
H40 H 0.7348 0.1185 0.5629 0.031 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.389(4) . ?
C1 C6 1.404(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.373(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.400(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.356(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.519(4) . ?
C7 C8 1.384(4) . ?
C7 C22 1.420(4) . ?
C8 C9 1.384(4) . ?
C8 H8 0.9500 . ?
C9 C16 1.423(4) . ?
C9 C10 1.497(4) . ?
C10 C11 1.379(4) . ?
C10 C15 1.401(4) . ?
C11 C12 1.395(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.425(4) . ?
C16 C17 1.425(4) . ?
C17 C18 1.352(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.422(4) . ?
C18 H18 0.9500 . ?
C19 C34 1.414(4) . ?
C19 C20 1.435(4) . ?
C20 C25 1.424(4) . ?
C20 C21 1.440(4) . ?
C21 C22 1.429(4) . ?
C22 C23 1.435(4) . ?
C23 C24 1.356(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.430(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.414(4) . ?
C26 C33 1.395(4) . ?
C26 C27 1.496(4) . ?
C27 C32 1.390(4) . ?
C27 C28 1.394(4) . ?
C28 C29 1.385(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.394(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.387(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.376(4) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C34 1.393(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.512(4) . ?
C35 C36 1.382(4) . ?
C35 C40 1.383(4) . ?
C36 C37 1.384(4) . ?
C36 H36 0.9500 . ?
C37 C38 1.387(4) . ?
C37 H37 0.9500 . ?
C38 C39 1.386(4) . ?
C38 H38 0.9500 . ?
C39 C40 1.395(4) . ?
C39 H39 0.9500 . ?
C40 H40 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 C1 C6 120.4(3) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 119.6(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 119.1(3) . . ?
C5 C6 C7 123.3(3) . . ?
C1 C6 C7 117.7(3) . . ?
C8 C7 C22 118.9(2) . . ?
C8 C7 C6 118.4(2) . . ?
C22 C7 C6 122.7(3) . . ?
C9 C8 C7 123.7(3) . . ?
C9 C8 H8 118.2 . . ?
C7 C8 H8 118.2 . . ?
C8 C9 C16 118.8(3) . . ?
C8 C9 C10 120.0(2) . . ?
C16 C9 C10 121.2(2) . . ?
C11 C10 C15 118.4(3) . . ?
C11 C10 C9 121.7(3) . . ?
C15 C10 C9 119.9(2) . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C12 C11 120.5(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 119.6(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C10 121.0(3) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C9 C16 C21 119.0(2) . . ?
C9 C16 C17 122.4(3) . . ?
C21 C16 C17 118.6(2) . . ?
C18 C17 C16 121.6(3) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C19 122.1(3) . . ?
C17 C18 H18 119.0 . . ?
C19 C18 H18 119.0 . . ?
C34 C19 C18 123.0(2) . . ?
C34 C19 C20 118.8(2) . . ?
C18 C19 C20 118.2(2) . . ?
C25 C20 C19 120.6(2) . . ?
C25 C20 C21 119.9(3) . . ?
C19 C20 C21 119.5(2) . . ?
C16 C21 C22 120.5(2) . . ?
C16 C21 C20 119.7(2) . . ?
C22 C21 C20 119.8(2) . . ?
C7 C22 C21 118.9(2) . . ?
C7 C22 C23 122.9(3) . . ?
C21 C22 C23 118.2(2) . . ?
C24 C23 C22 121.6(3) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C23 C24 C25 121.9(3) . . ?
C23 C24 H24 119.0 . . ?
C25 C24 H24 119.0 . . ?
C26 C25 C20 119.1(2) . . ?
C26 C25 C24 122.5(2) . . ?
C20 C25 C24 118.4(2) . . ?
C33 C26 C25 118.9(2) . . ?
C33 C26 C27 117.4(2) . . ?
C25 C26 C27 123.7(2) . . ?
C32 C27 C28 118.7(3) . . ?
C32 C27 C26 120.7(3) . . ?
C28 C27 C26 120.3(2) . . ?
C29 C28 C27 120.9(3) . . ?
C29 C28 H28 119.5 . . ?
C27 C28 H28 119.5 . . ?
C28 C29 C30 119.8(3) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C31 C30 C29 119.1(3) . . ?
C31 C30 H30 120.5 . . ?
C29 C30 H30 120.5 . . ?
C32 C31 C30 121.0(3) . . ?
C32 C31 H31 119.5 . . ?
C30 C31 H31 119.5 . . ?
C31 C32 C27 120.5(3) . . ?
C31 C32 H32 119.8 . . ?
C27 C32 H32 119.8 . . ?
C34 C33 C26 123.1(3) . . ?
C34 C33 H33 118.4 . . ?
C26 C33 H33 118.4 . . ?
C33 C34 C19 119.1(2) . . ?
C33 C34 C35 117.7(2) . . ?
C19 C34 C35 123.2(2) . . ?
C36 C35 C40 119.7(3) . . ?
C36 C35 C34 119.1(2) . . ?
C40 C35 C34 120.9(2) . . ?
C37 C36 C35 120.3(3) . . ?
C37 C36 H36 119.8 . . ?
C35 C36 H36 119.8 . . ?
C36 C37 C38 120.3(3) . . ?
C36 C37 H37 119.8 . . ?
C38 C37 H37 119.8 . . ?
C39 C38 C37 119.5(3) . . ?
C39 C38 H38 120.2 . . ?
C37 C38 H38 120.2 . . ?
C38 C39 C40 120.0(3) . . ?
C38 C39 H39 120.0 . . ?
C40 C39 H39 120.0 . . ?
C35 C40 C39 120.1(3) . . ?
C35 C40 H40 119.9 . . ?
C39 C40 H40 119.9 . . ?

_refine_diff_density_max         0.144
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.037

