# Electronic Supplementary Material (ESI) for ChemComm.
# 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_WUF-52(ds1-83-1p-42(1)m)
_database_code_depnum_ccdc_archive 'CCDC 2022084'
loop_
_audit_author_name
_audit_author_address
'Christopher Richardson'
;University of Wollongong
Australia
;
_audit_update_record             
;
2020-08-06 deposited with the CCDC.	2020-09-09 downloaded from the CCDC.
;
_audit_creation_date             2020-08-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            WUF-52
_chemical_name_systematic        ?
_chemical_formula_moiety         'C51 H33 N3 O13 Zn4'
_chemical_formula_sum            'C51 H33 N3 O13 Zn4'
_chemical_formula_weight         1157.28
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           113
_space_group_name_H-M_alt        'P -4 21 m'
_space_group_name_Hall           'P -4 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
'-y+1/2, -x+1/2, z'
'y+1/2, x+1/2, z'

_cell_length_a                   17.2000(12)
_cell_length_b                   17.2000(12)
_cell_length_c                   17.2000(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5088.4(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6446
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      58.900
_cell_measurement_theta_min      5.752
_shelx_estimated_absorpt_T_max   0.877
_shelx_estimated_absorpt_T_min   0.877
_exptl_absorpt_coefficient_mu    1.346
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.421
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR; Higashi, 1995'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    0.755
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       chip
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2457
_diffrn_reflns_av_unetI/netI     0.1933
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28491
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        58.900
_diffrn_reflns_theta_max         58.900
_diffrn_reflns_theta_min         5.752
_diffrn_ambient_temperature      292
_diffrn_detector                 RX
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
scan:
	Number of images: 56
	           Slice: 20.0000 - 160.0000
	     Image width: 2.5000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 90.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 44
	           Slice: 102.0000 - 212.0000
	     Image width: 2.5000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 180.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 56
	           Slice: 20.0000 - 160.0000
	     Image width: 2.5000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 30.0000
	             Phi: 90.0000
	             XTD: 127.4000
	          2theta: 0.0000
scan:
	Number of images: 44
	           Slice: 102.0000 - 212.0000
	     Image width: 2.5000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 30.0000
	             Phi: 180.0000
	             XTD: 127.4000
	          2theta: 0.0000
;
_diffrn_measurement_device       
;
Crystal Goniometer
;
_diffrn_measurement_device_type  
;
Rigaku RAXIS conversion
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type       FS_PROCESS
_diffrn_orient_matrix_UB_11      -0.022675
_diffrn_orient_matrix_UB_12      0.053530
_diffrn_orient_matrix_UB_13      -0.000134
_diffrn_orient_matrix_UB_21      0.013722
_diffrn_orient_matrix_UB_22      0.005672
_diffrn_orient_matrix_UB_23      -0.056207
_diffrn_orient_matrix_UB_31      -0.051742
_diffrn_orient_matrix_UB_32      -0.021954
_diffrn_orient_matrix_UB_33      -0.014848
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.799
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2884
_reflns_number_total             3824
_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       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.652
_refine_diff_density_rms         0.108
_refine_ls_abs_structure_details 
;
 Flack x determined using 829 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.37(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3824
_refine_ls_number_restraints     149
_refine_ls_R_factor_all          0.1106
_refine_ls_R_factor_gt           0.1015
_refine_ls_restrained_S_all      1.104
_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)+(0.1179P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2332
_refine_ls_wR_factor_ref         0.2487
_refine_special_details          
'Refined as a three-component twin [0 0 1 1 0 0 0 1 0]. BASF 0.27; 0.30. Flack N/A.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.426(9)
 0.271(6) 0.303(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 N14-C12
 1.4 with sigma of 0.01
 N29-C27
 1.4 with sigma of 0.01
 C27-C30
 2.4 with sigma of 0.04
4. Restrained planarity
 C25, C26, C27, C28
 with sigma of 0.1
5. Uiso/Uaniso restraints and constraints
C7 \\sim C8 \\sim C9 \\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C15 \\sim
C16 \\sim C17 \\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C24 \\sim
C25 \\sim C26 \\sim C27 \\sim C28 \\sim C30 \\sim C31 \\sim C32 \\sim O1 \\sim
O4 \\sim O5 \\sim O6 \\sim O23: within 1.7A with sigma of 0.01 and sigma for
terminal atoms of 0.02
6. Same fragment restrains
{C7, C8, C9, C10, C11} sigma for 1-2: 0.001, 1-3: 0.02
as
{C18, C19, C20, C21, C22}
{C7, C8, C9, C10, C11} sigma for 1-2: 0.001, 1-3: 0.02
as
{C24, C25, C26, C27, C28}
7. Others
 Fixed Sof: H12(0.5) N14(0.5) H14(0.5) C15(0.5) H15A(0.5) H15B(0.5) C16(0.5)
 C17(0.5) H17(0.5) C20(0.5) H20(0.5) C21(0.5) H21(0.5) N29(0.25) H29(0.25)
 C30(0.25) H30A(0.25) H30B(0.25) C31(0.25) C32(0.25) H32(0.25) H27(0.25)
 Fixed Uiso: N14(0.2) H14(0.2) C15(0.2) H15A(0.2) H15B(0.2) C16(0.2) C17(0.2)
 H17(0.2) N29(0.2) H29(0.2) C30(0.2) H30A(0.2) H30B(0.2) C31(0.2) C32(0.2)
 H32(0.2) H27(0.2)
 Fixed X: N14(0.61565) H14(0.61675) C15(0.63145) H15A(0.68515) H15B(0.627201)
 C16(0.58531) C17(0.550261) H17(0.523101) N29(0.607) H29(0.61275) C30(0.577649)
 H30A(0.56563) H30B(0.52763) C31(0.60381) C32(0.6386) H32(0.66555) H27(0.587)
 Fixed Y: N14(0.544479) H14(0.495449) C15(0.561151) H15A(0.54719)
 H15B(0.61695) C16(0.525391) C17(0.49154) H17(0.46531) N29(1.107) H29(1.101181)
 C30(1.18115) H30A(1.202769) H30B(1.16989) C31(1.24588) C32(1.29707)
 H32(1.336729) H27(1.087)
 Fixed Z: N14(0.702489) H14(0.69274) C15(0.78092) H15A(0.79102) H15B(0.78786)
 C16(0.83782) C17(0.88778) H17(0.926489) N29(1.158001) H29(1.10867)
 C30(1.17584) H30A(1.125161) H30B(1.199321) C31(1.21794) C32(1.25018)
 H32(1.275169) H27(1.16973)
8.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13), C20(H20), C21(H21), C26(H26)
8.b Fitted hexagon refined as free rotating group:
 C8(C9,C10,C11,C12,C13)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   geom
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 0.500000 1.000000 0.6279(15) 0.077(4) Uani 1 4 d S TU P . .
Zn2 Zn 0.43524(10) 0.93524(10) 0.56126(19) 0.0828(7) Uani 1 2 d S T P . .
Zn3 Zn 0.56549(11) 0.93451(11) 0.6921(2) 0.0906(9) Uani 1 2 d S T P . .
O4 O 0.4464(8) 0.8266(6) 0.5806(13) 0.133(4) Uani 1 1 d . U . . .
O5 O 0.5506(8) 0.8263(7) 0.6615(12) 0.133(5) Uani 1 1 d . U . . .
O6 O 0.5461(13) 0.9539(13) 0.7983(13) 0.165(9) Uani 1 2 d S TU P . .
C7 C 0.4986(11) 0.7934(7) 0.6201(18) 0.128(4) Uani 1 1 d D U . . .
C8 C 0.5030(8) 0.7052(4) 0.6143(10) 0.137(4) Uani 1 1 d D U . . .
C9 C 0.4418(8) 0.6646(5) 0.5807(10) 0.140(5) Uani 1 1 d DG U . . .
H9 H 0.403316 0.691166 0.553615 0.168 Uiso 1 1 calc R . . . .
C10 C 0.4381(8) 0.5841(5) 0.5876(12) 0.143(5) Uani 1 1 d DG U . . .
H10 H 0.397129 0.556920 0.565156 0.171 Uiso 1 1 calc R . . . .
C11 C 0.4956(9) 0.5444(4) 0.6281(13) 0.150(5) Uani 1 1 d DG U . . .
C12 C 0.5569(8) 0.5850(6) 0.6617(10) 0.155(5) Uani 1 1 d DG U . . .
H12 H 0.595361 0.558411 0.688778 0.186 Uiso 0.5 1 calc R . . A 2
C13 C 0.5606(7) 0.6655(6) 0.6548(10) 0.156(5) Uani 1 1 d G U . . .
H13 H 0.601549 0.692657 0.677238 0.187 Uiso 1 1 calc R . . . .
N14 N 0.615650 0.544479 0.702489 0.200 Uiso 0.5 1 d D . . B 1
H14 H 0.616750 0.495449 0.692740 0.200 Uiso 0.5 1 d . . . C 1
C15 C 0.631450 0.561151 0.780920 0.200 Uiso 0.5 1 d . U . B 1
H15A H 0.685150 0.547190 0.791020 0.200 Uiso 0.5 1 d . . . D 1
H15B H 0.627201 0.616950 0.787860 0.200 Uiso 0.5 1 d . . . E 1
C16 C 0.585310 0.525391 0.837820 0.200 Uiso 0.5 1 d . U . B 1
C17 C 0.550261 0.491540 0.887780 0.200 Uiso 0.5 1 d . U . B 1
H17 H 0.523101 0.465310 0.926489 0.200 Uiso 0.5 1 d . . . F 1
C18 C 0.500000 1.000000 0.8300(13) 0.165(9) Uani 1 4 d DS TU P G .
C19 C 0.500000 1.000000 0.9185(13) 0.169(9) Uani 1 4 d DS TU P . .
C20 C 0.476(3) 1.0672(11) 0.9564(11) 0.169(9) Uani 0.5 1 d D U . G -1
H20 H 0.459063 1.109974 0.927964 0.202 Uiso 0.5 1 calc R . . G -1
C21 C 0.478(3) 1.0701(11) 1.0372(11) 0.173(9) Uani 0.5 1 d D U . G -1
H21 H 0.465452 1.114327 1.065745 0.207 Uiso 0.5 1 calc R . . G -1
C22 C 0.500000 1.000000 1.0707(18) 0.182(9) Uani 1 4 d DS TU P . .
O23 O 0.5450(10) 1.0450(10) 1.4420(15) 0.150(7) Uani 1 2 d S TU P . .
C24 C 0.500000 1.000000 1.4055(12) 0.144(8) Uani 1 4 d DS TU P . .
C25 C 0.500000 1.000000 1.3171(11) 0.156(8) Uani 1 4 d DS TU P . .
C26 C 0.5497(5) 1.0497(5) 1.2771(10) 0.174(8) Uani 1 2 d DS TU P G .
H26 H 0.582211 1.082211 1.305484 0.208 Uiso 1 2 calc RS T P . .
C27 C 0.5526(4) 1.0526(4) 1.1964(10) 0.182(9) Uani 1 2 d DS TU P . .
C28 C 0.500000 1.000000 1.1649(18) 0.181(9) Uani 1 4 d DS TU P G .
N29 N 0.607000 1.107000 1.158001 0.200 Uiso 0.25 1 d DS T P G -1
H29 H 0.612750 1.101181 1.108669 0.200 Uiso 0.25 1 d . . . H -1
C30 C 0.577649 1.181150 1.175840 0.200 Uiso 0.25 1 d D U . G -1
H30A H 0.565630 1.202770 1.125160 0.200 Uiso 0.25 1 d . . . I -1
H30B H 0.527630 1.169891 1.199322 0.200 Uiso 0.25 1 d . . . J -1
C31 C 0.603810 1.245880 1.217941 0.200 Uiso 0.25 1 d . U . G -1
C32 C 0.638600 1.297070 1.250179 0.200 Uiso 0.25 1 d . U . G -1
H32 H 0.665550 1.336729 1.275169 0.200 Uiso 0.25 1 d . . . K -1
H27 H 0.587000 1.087000 1.169731 0.200 Uiso 0.5 2 d S T P L 1


_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 Zn2 1.948(16) 2_675 ?
O1 Zn2 1.948(16) . ?
O1 Zn3 1.939(15) . ?
O1 Zn3 1.939(15) 2_675 ?
Zn2 Zn2 3.151(5) 2_675 ?
Zn2 O4 1.908(11) . ?
Zn2 O4 1.908(11) 8_455 ?
Zn2 O23 2.11(3) 2_674 ?
Zn3 O5 1.950(12) . ?
Zn3 O5 1.950(12) 7_665 ?
Zn3 O6 1.89(2) . ?
O4 C7 1.26(2) . ?
O5 C7 1.28(2) . ?
O6 C18 1.25(3) . ?
C7 C8 1.521(12) . ?
C8 C9 1.3900 . ?
C8 C13 1.3900 . ?
C9 H9 0.9300 . ?
C9 C10 1.3900 . ?
C10 H10 0.9300 . ?
C10 C11 1.3900 . ?
C11 C11 1.533(13) 2_665 ?
C11 C12 1.3900 . ?
C12 H12 0.9300 . ?
C12 C13 1.3900 . ?
C12 N14 1.415(8) . ?
C13 H13 0.9300 . ?
N14 H14 0.86004(8) . ?
N14 C15 1.40567(9) . ?
C15 H15A 0.97003(6) . ?
C15 H15B 0.96990(6) . ?
C15 C16 1.40212(7) . ?
C16 C17 1.20035(6) . ?
C17 C17 1.75332(12) 2_665 ?
C17 H17 0.93008(5) . ?
C18 C19 1.522(12) . ?
C19 C20 1.3903(14) . ?
C20 H20 0.9300 . ?
C20 C21 1.3903(14) . ?
C21 H21 0.9300 . ?
C21 C22 1.3903(14) . ?
C22 C28 1.62(5) . ?
O23 C24 1.26(3) . ?
C24 C25 1.522(12) . ?
C25 C26 1.3902(14) 2_675 ?
C25 C26 1.3902(14) . ?
C26 H26 0.9300 . ?
C26 C27 1.3904(14) . ?
C27 C28 1.3905(14) . ?
C27 N29 1.478(9) . ?
C27 H27 0.953(10) . ?
N29 H29 0.86009(6) . ?
N29 C30 1.40556(9) . ?
C30 H30A 0.96999(6) . ?
C30 H30B 0.96994(4) . ?
C30 C31 1.40228(8) . ?
C31 C32 1.20031(7) . ?
C32 H32 0.93002(3) . ?

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
Zn2 O1 Zn2 108.0(13) 2_675 . ?
Zn3 O1 Zn2 109.58(8) 2_675 . ?
Zn3 O1 Zn2 109.58(8) . 2_675 ?
Zn3 O1 Zn2 109.58(8) . . ?
Zn3 O1 Zn2 109.58(8) 2_675 2_675 ?
Zn3 O1 Zn3 110.5(13) 2_675 . ?
O1 Zn2 Zn2 36.0(6) . 2_675 ?
O1 Zn2 O23 112.8(9) . 2_674 ?
O4 Zn2 O1 113.6(6) 8_455 . ?
O4 Zn2 O1 113.6(6) . . ?
O4 Zn2 Zn2 128.4(4) . 2_675 ?
O4 Zn2 Zn2 128.4(4) 8_455 2_675 ?
O4 Zn2 O4 99.6(9) 8_455 . ?
O4 Zn2 O23 108.2(8) 8_455 2_674 ?
O4 Zn2 O23 108.2(8) . 2_674 ?
O23 Zn2 Zn2 76.8(7) 2_674 2_675 ?
O1 Zn3 O5 108.9(6) . 7_665 ?
O1 Zn3 O5 108.9(6) . . ?
O5 Zn3 O5 100.2(9) . 7_665 ?
O6 Zn3 O1 110.3(11) . . ?
O6 Zn3 O5 114.0(8) . 7_665 ?
O6 Zn3 O5 114.0(8) . . ?
C7 O4 Zn2 127.5(12) . . ?
C7 O5 Zn3 131.8(11) . . ?
C18 O6 Zn3 130(2) . . ?
O4 C7 O5 126.7(12) . . ?
O4 C7 C8 116.9(17) . . ?
O5 C7 C8 116.3(16) . . ?
C9 C8 C7 119.4(10) . . ?
C9 C8 C13 120.0 . . ?
C13 C8 C7 119.6(11) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C11 124.0(17) . 2_665 ?
C10 C11 C12 120.0 . . ?
C12 C11 C11 115.2(19) . 2_665 ?
C11 C12 H12 120.0 . . ?
C11 C12 N14 120.0(9) . . ?
C13 C12 C11 120.0 . . ?
C13 C12 H12 120.0 . . ?
C13 C12 N14 120.0(9) . . ?
C8 C13 H13 120.0 . . ?
C12 C13 C8 120.0 . . ?
C12 C13 H13 120.0 . . ?
C12 N14 H14 113.7(6) . . ?
C15 N14 C12 120.9(7) . . ?
C15 N14 H14 112.512(1) . . ?
N14 C15 H15A 107.8 . . ?
N14 C15 H15B 107.782(1) . . ?
H15A C15 H15B 107.1 . . ?
C16 C15 N14 118.097(4) . . ?
C16 C15 H15A 107.779(2) . . ?
C16 C15 H15B 107.790(2) . . ?
C17 C16 C15 175.366(1) . . ?
C16 C17 C17 114.503(1) . 2_665 ?
C16 C17 H17 180.0 . . ?
C17 C17 H17 65.495(1) 2_665 . ?
O6 C18 O6 128(3) 2_675 . ?
O6 C18 C19 115.9(15) . . ?
O6 C18 C19 115.9(15) 2_675 . ?
C20 C19 C18 118.0(10) . . ?
C19 C20 H20 120.3 . . ?
C19 C20 C21 119.5(14) . . ?
C21 C20 H20 120.3 . . ?
C20 C21 H21 123.5 . . ?
C20 C21 C22 112.9(16) . . ?
C22 C21 H21 123.5 . . ?
C21 C22 C28 114.5(12) . . ?
C24 O23 Zn2 133.0(19) . 2_676 ?
O23 C24 O23 120(3) . 2_675 ?
O23 C24 C25 119.8(14) . . ?
O23 C24 C25 119.8(14) 2_675 . ?
C26 C25 C24 119.6(10) 2_675 . ?
C26 C25 C24 119.6(9) . . ?
C26 C25 C26 120.7(19) . 2_675 ?
C25 C26 H26 118.7 . . ?
C25 C26 C27 122.6(14) . . ?
C27 C26 H26 118.7 . . ?
C26 C27 C28 110.0(13) . . ?
C26 C27 N29 119.5(8) . . ?
C26 C27 H27 121.7(11) . . ?
C28 C27 N29 130.5(9) . . ?
C28 C27 H27 128.3(9) . . ?
N29 C27 H27 2.2(3) . . ?
C27 C28 C22 112.9(10) . . ?
C27 C28 C22 112.9(10) 2_675 . ?
C27 C28 C27 134(2) 2_675 . ?
C27 N29 H29 116.1(6) . . ?
C30 N29 C27 104.4(2) . . ?
C30 N29 H29 111.239(1) . . ?
N29 C30 H30A 103.193(4) . . ?
N29 C30 H30B 103.198(1) . . ?
H30A C30 H30B 105.171(3) . . ?
C31 C30 N29 135.881(1) . . ?
C31 C30 H30A 103.184(4) . . ?
C31 C30 H30B 103.186(3) . . ?
C32 C31 C30 168.788(1) . . ?
C31 C32 H32 179.986(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Zn3 O6 C18 0.000(13) . . . . ?
Zn2 O4 C7 O5 7(4) . . . . ?
Zn2 O4 C7 C8 -169.0(16) . . . . ?
Zn2 O23 C24 O23 0.000(8) 2_676 . . 2_675 ?
Zn2 O23 C24 C25 180.000(5) 2_676 . . . ?
Zn3 O5 C7 O4 9(4) . . . . ?
Zn3 O5 C7 C8 -175.3(15) . . . . ?
Zn3 O6 C18 O6 0.00(2) . . . 2_675 ?
Zn3 O6 C18 C19 180.000(12) . . . . ?
O4 C7 C8 C9 -13(3) . . . . ?
O4 C7 C8 C13 178.3(18) . . . . ?
O5 Zn3 O6 C18 -122.9(6) . . . . ?
O5 Zn3 O6 C18 122.9(6) 7_665 . . . ?
O5 C7 C8 C9 170.0(18) . . . . ?
O5 C7 C8 C13 2(3) . . . . ?
O6 C18 C19 C20 155(2) . . . . ?
O6 C18 C19 C20 -25(2) 2_675 . . . ?
C7 C8 C9 C10 -168(2) . . . . ?
C7 C8 C13 C12 168(2) . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C9 C8 C13 C12 0.0 . . . . ?
C9 C10 C11 C11 -169.7(15) . . . 2_665 ?
C9 C10 C11 C12 0.0 . . . . ?
C10 C11 C12 C13 0.0 . . . . ?
C10 C11 C12 N14 -179.6(16) . . . . ?
C11 C11 C12 C13 170.6(11) 2_665 . . . ?
C11 C11 C12 N14 -9.0(15) 2_665 . . . ?
C11 C12 C13 C8 0.0 . . . . ?
C11 C12 N14 C15 -121.8(10) . . . . ?
C12 N14 C15 C16 83.6(7) . . . . ?
C13 C8 C9 C10 0.0 . . . . ?
C13 C12 N14 C15 58.6(14) . . . . ?
N14 C12 C13 C8 179.6(16) . . . . ?
C18 C19 C20 C21 -178(4) . . . . ?
C19 C20 C21 C22 -4(7) . . . . ?
C20 C21 C22 C28 -178(3) . . . . ?
C21 C22 C28 C27 117(2) . . . 2_675 ?
C21 C22 C28 C27 -63(2) . . . . ?
O23 C24 C25 C26 0.000(2) 2_675 . . 2_675 ?
O23 C24 C25 C26 180.000(2) 2_675 . . . ?
O23 C24 C25 C26 0.000(3) . . . . ?
O23 C24 C25 C26 180.000(2) . . . 2_675 ?
C24 C25 C26 C27 180.000(3) . . . . ?
C25 C26 C27 C28 0.000(4) . . . . ?
C25 C26 C27 N29 180.000(2) . . . . ?
C26 C25 C26 C27 0.000(3) 2_675 . . . ?
C26 C27 C28 C22 180.000(4) . . . . ?
C26 C27 C28 C27 0.000(5) . . . 2_675 ?
C26 C27 N29 C30 -67.64(15) . . . . ?
C27 N29 C30 C31 116.0(6) . . . . ?
C28 C27 N29 C30 112.36(15) . . . . ?
N29 C27 C28 C22 0.000(5) . . . . ?
N29 C27 C28 C27 180.000(2) . . . 2_675 ?
N29 C30 C31 C32 30.344(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.426(9)
2 0.271(6)
3 0.303(6)

# start Validation Reply Form
_vrf_STRVA01_WUF-52ds1-83-1p-421m 
;
PROBLEM: Flack test results are ambiguous.
RESPONSE: Sure. The crystal is a 3-component twin. Used TWIN/BASF
refinement. See refine_ls_abs_structure_details
;
_vrf_PLAT602_WUF-52ds1-83-1p-421m 
;
PROBLEM: Solvent Accessible VOID(S) in Structure ........          ! Check 
RESPONSE: This is expected - this is a highly porous MOF with ca. 
0.9 nm channels.
;
_vrf_PLAT234_WUF-52ds1-83-1p-421m 
;
PROBLEM: Large Hirshfeld Difference Zn3--O6       .       0.18 Ang.  
RESPONSE: ...
;
_vrf_PLAT241_WUF-52ds1-83-1p-421m 
;
PROBLEM: High 'MainMol' Ueq as Compared to Neighbors of         O4 Check 
RESPONSE:  O4 coordinates to zinc and seems high compared to the 
heavier bonding partner. This is also a exacerbated by binding 
to Zn2, which is low.
;
_vrf_PLAT242_WUF-52ds1-83-1p-421m 
;
PROBLEM: Low 'MainMol' Ueq as Compared to Neighbors of Zn2 Check 
RESPONSE: Zn2 is low and this is typical of heavier atoms in a chain bonded
to lighter atoms around it.
;
_vrf_PLAT260_WUF-52ds1-83-1p-421m 
;
PROBLEM: Large Average Ueq of Residue Including       Zn2      0.147 Check 
RESPONSE: ...
;
_vrf_PLAT369_WUF-52ds1-83-1p-421m 
;
PROBLEM: Long C(sp2)-C(sp2) Bond  C11- C11_a.       1.53 Ang.  
RESPONSE: This is a bit long and a contributing reason is the modelling
of the phenyl rings as regular hexagons. This is actually a remarkably
good refinement of one of these IRMOF-9 systems and no further action is
being taken here.
;
_vrf_PLAT420_WUF-52ds1-83-1p-421m 
;
PROBLEM: D-H Without Acceptor       N14--H14.     Please Check 
RESPONSE: Solvent atoms that would act as H-bond acceptors lie in the pores of 
the MOF and are unresolved.
;
_vrf_PLAT910_WUF-52ds1-83-1p-421m 
;
PROBLEM: Missing number of FCF Reflection(s) Below Theta(Min).          6 Note  
RESPONSE: The SHEL command has been used (8 0.9) and a number of low 
angle reflections are omitted.
;
_vrf_PLAT911_WUF-52ds1-83-1p-421m 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.555         20 Report
RESPONSE: ...
;
_vrf_RINTA01_WUF-52ds1-83-1p-421m 
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: The trilling of this sample will affect the 
agreement factors.
;
_vrf_THETM01_WUF-52ds1-83-1p-421m 
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: This is very close. The data is truncated to approximately this value.
;
_vrf_PLAT049_WUF-52ds1-83-1p-421m 
;
PROBLEM: Calculated Density Less Than 1.0 gcm-3 ......... 0.7554 Check
RESPONSE: Expected for a MOF with this porosity.
;
_vrf_PLAT341_WUF-52ds1-83-1p-421m 
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.0196 Ang.
RESPONSE: This is a low resolution and low precision structure due to the nature
of the sample. In our experience of a number of these structures this sample 
is actually pretty good.
;
_vrf_PLAT987_WUF-52ds1-83-1p-421m 
;
PROBLEM: The Flack x is >> 0 - Do a BASF/TWIN Refinement Please Check
RESPONSE: We have done the BASF/TWIN refinement and report the results 
in the refine special details to make other aware of what we have done.
;
_chemical_properties_physical    Moisture-sensitive
####################################################################### 
# 
# 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_exp_197_mf2
_database_code_depnum_ccdc_archive 'CCDC 2022085'
loop_
_audit_author_name
_audit_author_address
'Christopher Richardson'
;University of Wollongong
Australia
;
_audit_update_record             
;
2020-08-06 deposited with the CCDC.	2020-09-09 downloaded from the CCDC.
;
_audit_creation_date             2020-07-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
"Dimethyl 2-(((1-(4,4'-bis(methoxycarbonyl)-[1,1'-biphenyl]-2-yl)-1H-1,2,3-triazol-4-yl)methyl)amino)-[1,1'-biphenyl]-4,4'-dicarboxylate"
_chemical_formula_moiety         'C35 H30 N4 O8'
_chemical_formula_sum            'C35 H30 N4 O8'
_chemical_formula_weight         634.63
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C35 H30 N4 O8'
_chemical_oxdiff_usercomment     'Triazole recollection in 40.47a'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   10.5406(3)
_cell_length_b                   10.8847(2)
_cell_length_c                   13.6301(4)
_cell_angle_alpha                94.515(2)
_cell_angle_beta                 101.132(2)
_cell_angle_gamma                96.424(2)
_cell_volume                     1516.65(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    27521
_cell_measurement_temperature    293(1)
_cell_measurement_theta_max      30.2840
_cell_measurement_theta_min      2.2360
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;CrysAlisPro 1.171.40.15 (Rigaku Oxford Diffraction, 2018) 
Analytical numeric absorption correction using a multifaceted crystal model
 based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897). 
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'faceted block'
_exptl_crystal_F_000             664
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 2 19 0.0991
-5 15 0 0.1712
-10 9 -8 0.1562
13 5 -3 0.1153
-6 0 19 0.1107
-13 0 13 0.1043
4 0 -19 0.1207
8 8 -15 0.1251
14 -1 3 0.1180
-12 9 8 0.1492
13 -5 4 0.1313
6 -8 -15 0.1324
7 -13 7 0.1365
-3 -14 -1 0.1275
-9 -8 -7 0.1341
-5 -7 17 0.1388
4 -5 17 0.1431
12 -9 -8 0.0938
13 6 -7 0.1251
1 14 6 0.1641
4 7 -17 0.1499
12 0 -15 0.1074
-13 -5 3 0.0860
-13 2 -5 0.1313
12 -2 -14 0.1082

_exptl_crystal_size_max          0.326
_exptl_crystal_size_mid          0.237
_exptl_crystal_size_min          0.201
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.9654 2.0193 19.0216 -0.5985 -0.5404 0.6177
-5.0042 15.0377 0.0011 -0.8955 0.4128 -0.2029
-10.0313 9.0159 -8.0062 -0.4804 0.2459 -0.8289
13.0197 5.0118 -3.0071 0.0540 0.7144 0.6635
-5.9734 0.0138 19.0227 -0.5684 -0.7512 0.3759
-12.9982 0.0085 13.0181 -0.5593 -0.8110 -0.2553
3.9697 -0.0140 -19.0222 0.5301 0.6845 -0.4911
7.9877 8.0098 -15.0190 0.0847 1.0113 -0.0633
14.0314 -0.9989 2.9994 0.2498 0.3419 0.9149
-12.0033 9.0278 8.0121 -0.9006 -0.2848 -0.3365
13.0302 -5.0084 4.0008 0.4200 0.1249 0.8726
5.9787 -8.0311 -15.0181 0.8995 0.3261 -0.2694
7.0225 -13.0271 7.0060 0.6601 -0.4717 0.5954
-3.0122 -14.0367 -1.0000 0.7128 -0.6123 -0.2903
-9.0331 -8.0266 -7.0050 0.4213 -0.4068 -0.8299
-4.9779 -7.0055 17.0204 -0.1283 -0.9304 0.3178
4.0394 -4.9995 17.0178 -0.0626 -0.5526 0.8477
12.0033 -9.0278 -8.0121 0.9006 0.2848 0.3365
13.0121 6.0113 -7.0116 0.0961 0.8690 0.5173
1.0184 14.0403 6.0061 -0.8705 0.4006 0.3650
3.9760 7.0054 -17.0201 0.1092 0.8970 -0.3754
11.9924 -0.0101 -15.0200 0.5878 0.8356 0.1217
-13.0197 -5.0118 3.0071 -0.0540 -0.7144 -0.6635
-13.0332 2.0000 -5.0019 -0.2362 -0.2119 -0.9276
11.9938 -2.0145 -14.0189 0.6706 0.7293 0.1483

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            79549
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.130
_diffrn_reflns_theta_min         2.247
_diffrn_ambient_temperature      293(1)
_diffrn_detector                 'HyPix Bantam HPC 3000'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00-141.53  368
  2  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00 137.28  368
  3  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00  60.00  368
  4  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00 -30.00  368
  5  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00-102.91  368
  6  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00   0.00  368
  7  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00   0.00  368
  8  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00-180.00  368
  9  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00  30.00  368
 10  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00-150.00  368
 11  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00 -60.00  368
 12  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00 120.00  368
 13  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00 -16.66  368
 14  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00-124.70  368
 15  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00 -90.00  368
 16  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00  82.70  368
 17  ω    -74.00  16.00   0.50   10.00    --   20.00  54.00 150.00  180
 18  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00 105.01  368
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (Paciorek et al (1999). Acta A55, 543-557)'
_diffrn_orient_matrix_UB_11      0.0191132000
_diffrn_orient_matrix_UB_12      -0.0531877000
_diffrn_orient_matrix_UB_13      -0.0238412000
_diffrn_orient_matrix_UB_21      0.0333206000
_diffrn_orient_matrix_UB_22      0.0385422000
_diffrn_orient_matrix_UB_23      -0.0290568000
_diffrn_orient_matrix_UB_31      0.0575222000
_diffrn_orient_matrix_UB_32      0.0056466000
_diffrn_orient_matrix_UB_33      0.0378199000
_diffrn_oxdiff_digest_frames     
;
018d9513798eabc009664e598c164744d306436010f
;
_diffrn_oxdiff_digest_hkl        
;
01a066a2cbc48b75db1b9deb1b24896839d75f
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5927
_reflns_number_total             8018
_reflns_odcompleteness_completeness 98.18
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.07
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     432
_refine_ls_number_reflns         8018
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.057
_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)+(0.0600P)²+0.2874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1249
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C20(H20),
 C25(H25), C26(H26), C28(H28), C31(H31), C32(H32), C34(H34), C35(H35)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C38(H38A,H38B,H38C), C42(H42A,H42B,H42C), C46(H46A,H46B,
 H46C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.18876(12) 0.40167(12) 0.14925(9) 0.0337(3) Uani 1 1 d . . . . .
C2 C 0.32209(12) 0.41077(12) 0.14212(9) 0.0325(3) Uani 1 1 d . . . . .
C3 C 0.39270(12) 0.52924(12) 0.15003(10) 0.0342(3) Uani 1 1 d . . . . .
H3 H 0.481165 0.536737 0.148957 0.041 Uiso 1 1 calc R . . . .
C4 C 0.33266(13) 0.63621(12) 0.15950(9) 0.0350(3) Uani 1 1 d . . . . .
C5 C 0.20123(13) 0.62775(13) 0.16365(11) 0.0403(3) Uani 1 1 d . . . . .
H5 H 0.160823 0.698907 0.169480 0.048 Uiso 1 1 calc R . . . .
C6 C 0.13165(13) 0.51035(13) 0.15887(11) 0.0394(3) Uani 1 1 d . . . . .
H6 H 0.043898 0.504107 0.162205 0.047 Uiso 1 1 calc R . . . .
C7 C 0.10522(12) 0.27941(12) 0.14012(10) 0.0347(3) Uani 1 1 d . . . . .
C8 C -0.01329(13) 0.25857(13) 0.07115(11) 0.0419(3) Uani 1 1 d . . . . .
H8 H -0.040063 0.321722 0.033047 0.050 Uiso 1 1 calc R . . . .
C9 C -0.09175(14) 0.14517(13) 0.05857(12) 0.0445(3) Uani 1 1 d . . . . .
H9 H -0.169907 0.132647 0.011583 0.053 Uiso 1 1 calc R . . . .
C10 C -0.05449(13) 0.04991(12) 0.11569(10) 0.0375(3) Uani 1 1 d . . . . .
C11 C 0.06079(14) 0.07145(13) 0.18784(11) 0.0422(3) Uani 1 1 d . . . . .
H11 H 0.085039 0.009690 0.228381 0.051 Uiso 1 1 calc R . . . .
C12 C 0.13972(13) 0.18478(13) 0.19952(11) 0.0417(3) Uani 1 1 d . . . . .
H12 H 0.216806 0.197887 0.247686 0.050 Uiso 1 1 calc R . . . .
C13 C -0.13967(14) -0.07241(13) 0.09478(11) 0.0408(3) Uani 1 1 d . . . . .
O14 O -0.09175(10) -0.15848(10) 0.15028(8) 0.0487(3) Uani 1 1 d . . . . .
C15 C -0.16901(16) -0.27992(14) 0.13372(13) 0.0501(4) Uani 1 1 d . . . . .
H15A H -0.178879 -0.312691 0.064806 0.075 Uiso 1 1 calc GR . . . .
H15B H -0.253363 -0.272571 0.148647 0.075 Uiso 1 1 calc GR . . . .
H15C H -0.125929 -0.334908 0.176751 0.075 Uiso 1 1 calc GR . . . .
O16 O -0.24017(11) -0.09183(10) 0.03304(10) 0.0599(3) Uani 1 1 d . . . . .
N17 N 0.38035(11) 0.30382(11) 0.12617(9) 0.0366(2) Uani 1 1 d . . . . .
H17 H 0.3268(17) 0.2421(18) 0.0980(14) 0.057(5) Uiso 1 1 d . . . . .
C18 C 0.49999(13) 0.31108(13) 0.08622(10) 0.0369(3) Uani 1 1 d . . . . .
H18A H 0.498612 0.375093 0.040512 0.044 Uiso 1 1 calc R . . . .
H18B H 0.502258 0.232556 0.048077 0.044 Uiso 1 1 calc R . . . .
N19 N 0.77209(10) 0.35187(10) 0.30068(8) 0.0328(2) Uani 1 1 d . . . . .
C20 C 0.64820(12) 0.30077(12) 0.26075(9) 0.0333(3) Uani 1 1 d . . . . .
H20 H 0.592965 0.250117 0.290697 0.040 Uiso 1 1 calc R . . . .
C21 C 0.62158(12) 0.33961(11) 0.16684(9) 0.0324(3) Uani 1 1 d . . . . .
N22 N 0.72937(11) 0.41272(11) 0.15340(9) 0.0406(3) Uani 1 1 d . . . . .
N23 N 0.82151(11) 0.42034(12) 0.23476(9) 0.0416(3) Uani 1 1 d . . . . .
C24 C 0.82488(12) 0.42200(12) 0.48404(10) 0.0350(3) Uani 1 1 d . . . . .
C25 C 0.90207(14) 0.40745(14) 0.57742(11) 0.0435(3) Uani 1 1 d . . . . .
H25 H 0.894489 0.457829 0.633805 0.052 Uiso 1 1 calc R . . . .
C26 C 0.98888(14) 0.32106(14) 0.58868(11) 0.0444(3) Uani 1 1 d . . . . .
H26 H 1.035866 0.312306 0.652336 0.053 Uiso 1 1 calc R . . . .
C27 C 1.00678(13) 0.24710(13) 0.50594(11) 0.0385(3) Uani 1 1 d . . . . .
C28 C 0.93669(12) 0.26293(13) 0.41106(10) 0.0368(3) Uani 1 1 d . . . . .
H28 H 0.950608 0.217107 0.354465 0.044 Uiso 1 1 calc R . . . .
C29 C 0.84607(12) 0.34694(12) 0.40068(10) 0.0332(3) Uani 1 1 d . . . . .
C30 C 0.72969(12) 0.51380(12) 0.48067(10) 0.0345(3) Uani 1 1 d . . . . .
C31 C 0.68158(13) 0.54451(13) 0.56748(10) 0.0393(3) Uani 1 1 d . . . . .
H31 H 0.705606 0.503375 0.624122 0.047 Uiso 1 1 calc R . . . .
C32 C 0.59924(13) 0.63462(13) 0.57047(10) 0.0399(3) Uani 1 1 d . . . . .
H32 H 0.571713 0.655846 0.629674 0.048 Uiso 1 1 calc R . . . .
C33 C 0.55747(13) 0.69357(12) 0.48546(10) 0.0365(3) Uani 1 1 d . . . . .
C34 C 0.60148(13) 0.66195(13) 0.39789(10) 0.0384(3) Uani 1 1 d . . . . .
H34 H 0.572580 0.699420 0.340118 0.046 Uiso 1 1 calc R . . . .
C35 C 0.68790(13) 0.57518(13) 0.39616(10) 0.0373(3) Uani 1 1 d . . . . .
H35 H 0.718691 0.557420 0.337805 0.045 Uiso 1 1 calc R . . . .
C36 C 0.46497(14) 0.78704(13) 0.48928(11) 0.0404(3) Uani 1 1 d . . . . .
O37 O 0.40586(11) 0.80973(11) 0.39800(8) 0.0560(3) Uani 1 1 d . . . . .
C38 C 0.31021(18) 0.89604(18) 0.39516(15) 0.0624(5) Uani 1 1 d . . . . .
H38A H 0.265173 0.897375 0.327018 0.094 Uiso 1 1 calc GR . . . .
H38B H 0.353414 0.977759 0.421166 0.094 Uiso 1 1 calc GR . . . .
H38C H 0.248713 0.870123 0.435419 0.094 Uiso 1 1 calc GR . . . .
O39 O 0.44468(13) 0.83664(11) 0.56618(9) 0.0581(3) Uani 1 1 d . . . . .
C40 C 1.09745(14) 0.15079(14) 0.51650(12) 0.0437(3) Uani 1 1 d . . . . .
O41 O 1.14778(11) 0.14217(10) 0.61314(8) 0.0508(3) Uani 1 1 d . . . . .
C42 C 1.23561(17) 0.05080(16) 0.63439(14) 0.0587(4) Uani 1 1 d . . . . .
H42A H 1.309491 0.069169 0.603952 0.088 Uiso 1 1 calc GR . . . .
H42B H 1.191256 -0.030269 0.607590 0.088 Uiso 1 1 calc GR . . . .
H42C H 1.264572 0.052632 0.705797 0.088 Uiso 1 1 calc GR . . . .
O43 O 1.12051(13) 0.08766(13) 0.44752(9) 0.0685(4) Uani 1 1 d . . . . .
C44 C 0.41549(14) 0.75797(12) 0.16368(10) 0.0379(3) Uani 1 1 d . . . . .
O45 O 0.34607(11) 0.85390(9) 0.15634(10) 0.0560(3) Uani 1 1 d . . . . .
C46 C 0.4220(2) 0.97504(15) 0.16231(18) 0.0737(6) Uani 1 1 d . . . . .
H46A H 0.478065 0.973008 0.114600 0.111 Uiso 1 1 calc GR . . . .
H46B H 0.473856 0.995845 0.228866 0.111 Uiso 1 1 calc GR . . . .
H46C H 0.364276 1.036369 0.147397 0.111 Uiso 1 1 calc GR . . . .
O47 O 0.53223(10) 0.76974(9) 0.17232(9) 0.0494(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
C1 C2 1.4204(18) . ?
C1 C6 1.3945(19) . ?
C1 C7 1.4937(17) . ?
C2 C3 1.4003(17) . ?
C2 N17 1.3969(17) . ?
C3 C4 1.3948(18) . ?
C4 C5 1.3905(19) . ?
C4 C44 1.4939(18) . ?
C5 C6 1.3905(19) . ?
C7 C8 1.3947(18) . ?
C7 C12 1.3965(18) . ?
C8 C9 1.3858(19) . ?
C9 C10 1.3912(19) . ?
C10 C11 1.3918(19) . ?
C10 C13 1.4946(18) . ?
C11 C12 1.3883(19) . ?
C13 O14 1.3323(17) . ?
C13 O16 1.2053(17) . ?
O14 C15 1.4500(17) . ?
N17 C18 1.4638(17) . ?
C18 C21 1.5032(17) . ?
N19 C20 1.3514(16) . ?
N19 N23 1.3540(15) . ?
N19 C29 1.4419(16) . ?
C20 C21 1.3671(18) . ?
C21 N22 1.3633(16) . ?
N22 N23 1.3159(16) . ?
C24 C25 1.4028(19) . ?
C24 C29 1.4146(18) . ?
C24 C30 1.4903(18) . ?
C25 C26 1.381(2) . ?
C26 C27 1.389(2) . ?
C27 C28 1.3938(19) . ?
C27 C40 1.4925(19) . ?
C28 C29 1.3900(18) . ?
C30 C31 1.4059(18) . ?
C30 C35 1.3993(18) . ?
C31 C32 1.3837(19) . ?
C32 C33 1.3898(19) . ?
C33 C34 1.3940(19) . ?
C33 C36 1.4905(19) . ?
C34 C35 1.3855(19) . ?
C36 O37 1.3344(18) . ?
C36 O39 1.2080(17) . ?
O37 C38 1.4502(18) . ?
C40 O41 1.3365(18) . ?
C40 O43 1.1997(18) . ?
O41 C42 1.4415(18) . ?
C44 O45 1.3397(17) . ?
C44 O47 1.2045(17) . ?
O45 C46 1.4517(19) . ?

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 C7 122.19(11) . . ?
C6 C1 C2 118.98(12) . . ?
C6 C1 C7 118.71(11) . . ?
C3 C2 C1 118.40(12) . . ?
N17 C2 C1 120.55(11) . . ?
N17 C2 C3 121.05(12) . . ?
C4 C3 C2 121.16(12) . . ?
C3 C4 C44 116.96(12) . . ?
C5 C4 C3 120.62(12) . . ?
C5 C4 C44 122.42(12) . . ?
C4 C5 C6 118.42(13) . . ?
C5 C6 C1 122.34(12) . . ?
C8 C7 C1 119.31(12) . . ?
C8 C7 C12 118.09(12) . . ?
C12 C7 C1 122.59(11) . . ?
C9 C8 C7 120.98(13) . . ?
C8 C9 C10 120.51(12) . . ?
C9 C10 C11 119.01(12) . . ?
C9 C10 C13 117.97(12) . . ?
C11 C10 C13 123.01(13) . . ?
C12 C11 C10 120.25(13) . . ?
C11 C12 C7 121.06(12) . . ?
O14 C13 C10 112.95(11) . . ?
O16 C13 C10 123.57(13) . . ?
O16 C13 O14 123.46(13) . . ?
C13 O14 C15 116.06(11) . . ?
C2 N17 C18 120.20(11) . . ?
N17 C18 C21 113.04(11) . . ?
C20 N19 N23 110.59(10) . . ?
C20 N19 C29 128.26(11) . . ?
N23 N19 C29 121.02(10) . . ?
N19 C20 C21 105.13(11) . . ?
C20 C21 C18 129.77(12) . . ?
N22 C21 C18 122.07(11) . . ?
N22 C21 C20 108.15(11) . . ?
N23 N22 C21 109.27(11) . . ?
N22 N23 N19 106.86(10) . . ?
C25 C24 C29 115.86(12) . . ?
C25 C24 C30 118.23(12) . . ?
C29 C24 C30 125.92(12) . . ?
C26 C25 C24 122.40(13) . . ?
C25 C26 C27 120.70(13) . . ?
C26 C27 C28 118.70(13) . . ?
C26 C27 C40 121.70(13) . . ?
C28 C27 C40 119.60(13) . . ?
C29 C28 C27 120.28(12) . . ?
C24 C29 N19 121.40(11) . . ?
C28 C29 N19 116.63(11) . . ?
C28 C29 C24 121.95(12) . . ?
C31 C30 C24 118.99(12) . . ?
C35 C30 C24 123.56(12) . . ?
C35 C30 C31 117.42(12) . . ?
C32 C31 C30 121.42(13) . . ?
C31 C32 C33 120.35(12) . . ?
C32 C33 C34 118.99(12) . . ?
C32 C33 C36 119.44(12) . . ?
C34 C33 C36 121.56(12) . . ?
C35 C34 C33 120.58(13) . . ?
C34 C35 C30 121.18(12) . . ?
O37 C36 C33 112.54(12) . . ?
O39 C36 C33 124.08(14) . . ?
O39 C36 O37 123.38(13) . . ?
C36 O37 C38 115.98(12) . . ?
O41 C40 C27 111.13(13) . . ?
O43 C40 C27 124.58(14) . . ?
O43 C40 O41 124.27(14) . . ?
C40 O41 C42 117.01(13) . . ?
O45 C44 C4 112.83(12) . . ?
O47 C44 C4 124.13(13) . . ?
O47 C44 O45 123.04(13) . . ?
C44 O45 C46 115.21(13) . . ?

_olex2_exptl_crystal_mounting_method 'Mitegen mount + Paratone'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.142
_oxdiff_exptl_absorpt_empirical_full_min 0.949

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol / dichloromethane'
