# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1896206'
loop_
_audit_author_name
_audit_author_address
'Benjamin Ward'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2019-02-08 deposited with the CCDC.	2019-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H23 N3 O2'
_chemical_formula_weight         373.44

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   19.1233(13)
_cell_length_b                   11.8499(8)
_cell_length_c                   8.8509(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.5430(10)
_cell_angle_gamma                90
_cell_volume                     1901.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11000
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            10893
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.894
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_point_group_measured_fraction_full 0.892
_reflns_number_total             3659
_reflns_number_gt                3615
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_max     0.679
_reflns_Friedel_fraction_full    0.787

_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       
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0517P)²+0.4950P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1449 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
# _refine_ls_abs_structure_Flack    -0.5(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3659
_refine_ls_number_parameters     262
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0786
_refine_ls_wR_factor_gt          0.0784
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
O1 O 0.86190(7) -0.12698(11) 0.78900(15) 0.0208(3) Uani 1 1 d D . . . .
O2 O 0.75280(8) 0.48829(12) 0.94700(17) 0.0280(3) Uani 1 1 d D . . . .
N1 N 0.99868(8) 0.36660(13) 0.98657(18) 0.0217(3) Uani 1 1 d . . . . .
N2 N 0.86737(8) 0.07567(12) 0.90389(17) 0.0179(3) Uani 1 1 d . . . . .
N3 N 0.77566(8) 0.32550(12) 0.77433(17) 0.0175(3) Uani 1 1 d . . . . .
C1 C 0.94579(9) 0.19658(15) 0.7088(2) 0.0200(3) Uani 1 1 d . . . . .
H1A H 0.9440 0.2417 0.6149 0.030 Uiso 1 1 calc R U . . .
H1B H 0.9245 0.1219 0.6747 0.030 Uiso 1 1 calc R U . . .
H1C H 0.9971 0.1882 0.7767 0.030 Uiso 1 1 calc R U . . .
C2 C 0.90118(9) 0.25621(14) 0.8031(2) 0.0163(3) Uani 1 1 d . . . . .
C3 C 0.93694(9) 0.37093(14) 0.8608(2) 0.0169(3) Uani 1 1 d . . . . .
C4 C 0.90974(10) 0.47263(15) 0.7867(2) 0.0230(4) Uani 1 1 d . . . . .
H4 H 0.8658 0.4741 0.6980 0.028 Uiso 1 1 calc R U . . .
C5 C 0.94740(11) 0.57214(16) 0.8439(2) 0.0255(4) Uani 1 1 d . . . . .
H5 H 0.9296 0.6422 0.7945 0.031 Uiso 1 1 calc R U . . .
C6 C 1.01105(10) 0.56801(15) 0.9732(2) 0.0223(4) Uani 1 1 d . . . . .
H6 H 1.0380 0.6346 1.0147 0.027 Uiso 1 1 calc R U . . .
C7 C 1.03410(10) 0.46371(15) 1.0401(2) 0.0235(4) Uani 1 1 d . . . . .
H7 H 1.0777 0.4605 1.1295 0.028 Uiso 1 1 calc R U . . .
C8 C 0.90218(9) 0.18596(14) 0.9510(2) 0.0177(3) Uani 1 1 d . . . . .
H8A H 0.9538 0.1751 1.0199 0.021 Uiso 1 1 calc R U . . .
H8B H 0.8756 0.2274 1.0131 0.021 Uiso 1 1 calc R U . . .
C9 C 0.80605(9) 0.05619(14) 0.9278(2) 0.0174(3) Uani 1 1 d . . . . .
H9 H 0.7862 0.1118 0.9799 0.021 Uiso 1 1 calc R U . . .
C10 C 0.76556(9) -0.04877(14) 0.8775(2) 0.0174(3) Uani 1 1 d . . . . .
C11 C 0.79485(9) -0.13682(14) 0.80856(19) 0.0177(3) Uani 1 1 d . . . . .
C12 C 0.75444(10) -0.23563(15) 0.7589(2) 0.0220(4) Uani 1 1 d . . . . .
H12 H 0.7740 -0.2947 0.7119 0.026 Uiso 1 1 calc R U . . .
C13 C 0.68558(10) -0.24742(16) 0.7782(2) 0.0249(4) Uani 1 1 d . . . . .
H13 H 0.6582 -0.3148 0.7440 0.030 Uiso 1 1 calc R U . . .
C14 C 0.65604(10) -0.16166(16) 0.8473(2) 0.0243(4) Uani 1 1 d . . . . .
H14 H 0.6089 -0.1705 0.8604 0.029 Uiso 1 1 calc R U . . .
C15 C 0.69606(9) -0.06332(15) 0.8966(2) 0.0205(3) Uani 1 1 d . . . . .
H15 H 0.6761 -0.0049 0.9440 0.025 Uiso 1 1 calc R U . . .
C16 C 0.82118(9) 0.26950(14) 0.6923(2) 0.0175(3) Uani 1 1 d . . . . .
H16A H 0.8208 0.3143 0.5976 0.021 Uiso 1 1 calc R U . . .
H16B H 0.8003 0.1942 0.6553 0.021 Uiso 1 1 calc R U . . .
C17 C 0.71168(9) 0.28608(14) 0.7609(2) 0.0174(3) Uani 1 1 d . . . . .
H17 H 0.6956 0.2186 0.7021 0.021 Uiso 1 1 calc R U . . .
C18 C 0.66285(9) 0.34302(14) 0.8344(2) 0.0170(3) Uani 1 1 d . . . . .
C19 C 0.68508(9) 0.44313(15) 0.9221(2) 0.0199(3) Uani 1 1 d . . . . .
C20 C 0.63598(10) 0.49867(16) 0.9848(2) 0.0247(4) Uani 1 1 d . . . . .
H20 H 0.6505 0.5666 1.0433 0.030 Uiso 1 1 calc R U . . .
C21 C 0.56629(10) 0.45498(16) 0.9617(2) 0.0236(4) Uani 1 1 d . . . . .
H21 H 0.5335 0.4928 1.0059 0.028 Uiso 1 1 calc R U . . .
C22 C 0.54350(10) 0.35613(16) 0.8746(2) 0.0225(4) Uani 1 1 d . . . . .
H22 H 0.4955 0.3266 0.8593 0.027 Uiso 1 1 calc R U . . .
C23 C 0.59171(9) 0.30136(14) 0.8105(2) 0.0203(3) Uani 1 1 d . . . . .
H23 H 0.5762 0.2347 0.7495 0.024 Uiso 1 1 calc R U . . .
H1O H 0.8753(16) -0.0596(19) 0.814(4) 0.047(8) Uiso 1 1 d D . . . .
H2O H 0.7745(16) 0.442(2) 0.900(4) 0.050(8) Uiso 1 1 d 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 C11 1.3524(19) . ?
O2 C19 1.353(2) . ?
N1 C3 1.342(2) . ?
N1 C7 1.343(2) . ?
N2 C9 1.277(2) . ?
N2 C8 1.466(2) . ?
N3 C17 1.279(2) . ?
N3 C16 1.459(2) . ?
C1 C2 1.542(2) . ?
C2 C3 1.534(2) . ?
C2 C16 1.540(2) . ?
C2 C8 1.546(2) . ?
C3 C4 1.391(2) . ?
C4 C5 1.390(3) . ?
C5 C6 1.381(3) . ?
C6 C7 1.381(3) . ?
C9 C10 1.458(2) . ?
C10 C15 1.403(2) . ?
C10 C11 1.411(2) . ?
C11 C12 1.395(2) . ?
C12 C13 1.388(3) . ?
C13 C14 1.395(3) . ?
C14 C15 1.386(3) . ?
C17 C18 1.462(2) . ?
C18 C23 1.399(2) . ?
C18 C19 1.407(2) . ?
C19 C20 1.397(2) . ?
C20 C21 1.383(3) . ?
C21 C22 1.394(3) . ?
C22 C23 1.388(2) . ?

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
C3 N1 C7 118.18(15) . . ?
C9 N2 C8 118.17(14) . . ?
C17 N3 C16 119.48(14) . . ?
C3 C2 C16 111.62(13) . . ?
C3 C2 C1 108.74(13) . . ?
C16 C2 C1 108.07(14) . . ?
C3 C2 C8 108.15(13) . . ?
C16 C2 C8 109.67(13) . . ?
C1 C2 C8 110.59(13) . . ?
N1 C3 C4 121.49(15) . . ?
N1 C3 C2 115.06(14) . . ?
C4 C3 C2 123.41(14) . . ?
C5 C4 C3 119.37(16) . . ?
C6 C5 C4 119.30(18) . . ?
C7 C6 C5 117.66(17) . . ?
N1 C7 C6 124.00(17) . . ?
N2 C8 C2 110.92(13) . . ?
N2 C9 C10 122.02(15) . . ?
C15 C10 C11 118.86(16) . . ?
C15 C10 C9 119.98(15) . . ?
C11 C10 C9 121.16(15) . . ?
O1 C11 C12 119.00(15) . . ?
O1 C11 C10 120.96(15) . . ?
C12 C11 C10 120.04(15) . . ?
C13 C12 C11 119.86(16) . . ?
C12 C13 C14 120.88(17) . . ?
C15 C14 C13 119.37(17) . . ?
C14 C15 C10 120.99(17) . . ?
N3 C16 C2 111.01(14) . . ?
N3 C17 C18 121.16(15) . . ?
C23 C18 C19 119.32(15) . . ?
C23 C18 C17 119.87(15) . . ?
C19 C18 C17 120.73(15) . . ?
O2 C19 C20 118.57(16) . . ?
O2 C19 C18 121.92(15) . . ?
C20 C19 C18 119.51(16) . . ?
C21 C20 C19 120.18(16) . . ?
C20 C21 C22 120.88(16) . . ?
C23 C22 C21 119.19(16) . . ?
C22 C23 C18 120.92(16) . . ?

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 H1O N2 0.85(2) 1.82(2) 2.597(2) 153(3) .
O2 H2O N3 0.87(2) 1.78(2) 2.583(2) 153(3) .

_refine_diff_density_max         0.175
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.044

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1896208'
loop_
_audit_author_name
_audit_author_address
'Benjamin Ward'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2019-02-08 deposited with the CCDC.	2019-05-14 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT097_4                   
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       1.36 eA-3
RESPONSE: The crystal of 4 was a non-merohedral twin (180\% about the direct axis [1 0 0]). The data were processed using CrysalisPro and a hklf5 file produced for the twin refinement. The structure contains residual maxima (1.362 e \%A--3) which were larger than desired, but these maxima do not correspond to any chemically reasonable atoms and are significantly reduced compared to the hlkf4 refinement. The refinement otherwise proceeded normally.
;
# Added during the CSD deposition process: Friday 08 February 2019 10:36 AM
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H28 Al N3 O3'
_chemical_formula_weight         505.53

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'
Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   13.4154(6)
_cell_length_b                   13.5031(6)
_cell_length_c                   14.8493(7)
_cell_angle_alpha                79.454(4)
_cell_angle_beta                 76.691(4)
_cell_angle_gamma                75.227(4)
_cell_volume                     2509.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    29581
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      27.5

_exptl_crystal_description       needle
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.119
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.614
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            17593
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.600
_diffrn_reflns_theta_max         27.634
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             17593
_reflns_number_gt                12728
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)
;
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Refined as a 2-component twin.

The crystal used was a non-merohedral twin (180 degrees about the direct 
axis 1 0 0). The data were processed using CrysalisPro and a hklf5 file
produced for the twin refinement.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1044P)²+2.4740P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         17593
_refine_ls_number_parameters     672
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1095
_refine_ls_R_factor_gt           0.0756
_refine_ls_wR_factor_ref         0.2050
_refine_ls_wR_factor_gt          0.1837
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_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
Al1 Al 0.90748(7) 0.79170(7) 0.78501(6) 0.0131(2) Uani 1 1 d . . . . .
Al2 Al 0.44539(7) 0.70678(7) 0.71508(6) 0.0116(2) Uani 1 1 d . . . . .
O1 O 0.91881(19) 0.67228(18) 0.86790(16) 0.0187(5) Uani 1 1 d . . . . .
O2 O 0.77433(18) 0.84377(18) 0.84831(15) 0.0159(5) Uani 1 1 d . . . . .
O3 O 0.85641(18) 0.74603(17) 0.70116(14) 0.0157(5) Uani 1 1 d . . . . .
O4 O 0.43552(18) 0.82797(17) 0.63446(15) 0.0163(5) Uani 1 1 d . . . . .
O5 O 0.37252(17) 0.65635(17) 0.64922(15) 0.0143(5) Uani 1 1 d . . . . .
O6 O 0.32700(17) 0.74758(17) 0.79925(15) 0.0149(5) Uani 1 1 d . . . . .
N1 N 0.9062(2) 0.9324(2) 0.69287(18) 0.0125(5) Uani 1 1 d . . . . .
N2 N 1.0639(2) 0.7502(2) 0.73244(18) 0.0153(6) Uani 1 1 d . . . . .
N3 N 0.9599(2) 0.8751(2) 0.86143(18) 0.0147(5) Uani 1 1 d . . . . .
N4 N 0.4708(2) 0.5633(2) 0.80357(18) 0.0125(5) Uani 1 1 d . . . . .
N5 N 0.5523(2) 0.7482(2) 0.77050(18) 0.0149(6) Uani 1 1 d . . . . .
N6 N 0.5812(2) 0.6272(2) 0.63827(19) 0.0148(5) Uani 1 1 d . . . . .
C1 C 1.1662(3) 0.9927(3) 0.6856(3) 0.0232(8) Uani 1 1 d . . . . .
H1A H 1.2275 0.9546 0.7126 0.035 Uiso 1 1 calc R U . . .
H1B H 1.1405 1.0605 0.7076 0.035 Uiso 1 1 calc R U . . .
H1C H 1.1863 1.0019 0.6174 0.035 Uiso 1 1 calc R U . . .
C2 C 1.0799(3) 0.9322(3) 0.7155(2) 0.0166(7) Uani 1 1 d . . . . .
C3 C 0.9823(3) 0.9869(3) 0.6759(2) 0.0149(6) Uani 1 1 d . . . . .
C4 C 0.9722(3) 1.0827(3) 0.6216(2) 0.0172(7) Uani 1 1 d . . . . .
H4 H 1.0263 1.1197 0.6103 0.021 Uiso 1 1 calc R U . . .
C5 C 0.8830(3) 1.1239(3) 0.5842(2) 0.0197(7) Uani 1 1 d . . . . .
H5 H 0.8751 1.1897 0.5472 0.024 Uiso 1 1 calc R U . . .
C6 C 0.8052(3) 1.0689(3) 0.6009(2) 0.0190(7) Uani 1 1 d . . . . .
H6 H 0.7433 1.0959 0.5757 0.023 Uiso 1 1 calc R U . . .
C7 C 0.8200(2) 0.9735(2) 0.6553(2) 0.0144(6) Uani 1 1 d . . . . .
H7 H 0.7669 0.9353 0.6667 0.017 Uiso 1 1 calc R U . . .
C8 C 1.1219(3) 0.8277(3) 0.6783(2) 0.0184(7) Uani 1 1 d . . . . .
H8A H 1.1155 0.8364 0.6120 0.022 Uiso 1 1 calc R U . . .
H8B H 1.1973 0.8029 0.6814 0.022 Uiso 1 1 calc R U . . .
C9 C 1.1217(3) 0.6593(3) 0.7489(2) 0.0178(7) Uani 1 1 d . . . . .
H9 H 1.1946 0.6494 0.7228 0.021 Uiso 1 1 calc R U . . .
C10 C 1.0847(3) 0.5715(3) 0.8035(2) 0.0197(7) Uani 1 1 d . . . . .
C11 C 1.1548(3) 0.4739(3) 0.8025(3) 0.0248(8) Uani 1 1 d . . . . .
H11 H 1.2223 0.4677 0.7634 0.030 Uiso 1 1 calc R U . . .
C12 C 1.1272(3) 0.3879(3) 0.8567(3) 0.0294(9) Uani 1 1 d . . . . .
H12 H 1.1752 0.3225 0.8563 0.035 Uiso 1 1 calc R U . . .
C13 C 1.0278(3) 0.3983(3) 0.9123(3) 0.0269(9) Uani 1 1 d . . . . .
H13 H 1.0075 0.3388 0.9493 0.032 Uiso 1 1 calc R U . . .
C14 C 0.9578(3) 0.4921(3) 0.9156(2) 0.0229(8) Uani 1 1 d . . . . .
H14 H 0.8906 0.4966 0.9551 0.027 Uiso 1 1 calc R U . . .
C15 C 0.9847(3) 0.5821(3) 0.8607(2) 0.0182(7) Uani 1 1 d . . . . .
C16 C 1.0558(3) 0.9145(3) 0.8228(2) 0.0199(7) Uani 1 1 d . . . . .
H16A H 1.1160 0.8647 0.8452 0.024 Uiso 1 1 calc R U . . .
H16B H 1.0478 0.9806 0.8465 0.024 Uiso 1 1 calc R U . . .
C17 C 0.9139(3) 0.8937(2) 0.9443(2) 0.0174(7) Uani 1 1 d . . . . .
H17 H 0.9490 0.9228 0.9781 0.021 Uiso 1 1 calc R U . . .
C18 C 0.8130(3) 0.8736(3) 0.9897(3) 0.0154(8) Uani 1 1 d . . . . .
C19 C 0.7768(3) 0.8880(3) 1.0839(2) 0.0225(7) Uani 1 1 d . . . . .
H19 H 0.8229 0.9025 1.1171 0.027 Uiso 1 1 calc R U . . .
C20 C 0.6771(3) 0.8818(3) 1.1294(2) 0.0259(8) Uani 1 1 d . . . . .
H20 H 0.6548 0.8888 1.1939 0.031 Uiso 1 1 calc R U . . .
C21 C 0.6089(3) 0.8650(3) 1.0779(3) 0.0264(8) Uani 1 1 d . . . . .
H21 H 0.5387 0.8626 1.1078 0.032 Uiso 1 1 calc R U . . .
C22 C 0.6415(3) 0.8517(3) 0.9845(2) 0.0224(7) Uani 1 1 d . . . . .
H22 H 0.5933 0.8406 0.9514 0.027 Uiso 1 1 calc R U . . .
C23 C 0.7449(3) 0.8544(2) 0.9379(2) 0.0162(6) Uani 1 1 d . . . . .
C24 C 0.8878(3) 0.7242(2) 0.6135(2) 0.0146(6) Uani 1 1 d . . . . .
C25 C 0.8238(3) 0.7680(3) 0.5470(2) 0.0184(7) Uani 1 1 d . . . . .
H25 H 0.7594 0.8157 0.5642 0.022 Uiso 1 1 calc R U . . .
C26 C 0.8533(3) 0.7428(3) 0.4569(2) 0.0250(8) Uani 1 1 d . . . . .
H26 H 0.8081 0.7732 0.4138 0.030 Uiso 1 1 calc R U . . .
C27 C 0.9468(3) 0.6748(3) 0.4280(3) 0.0310(9) Uani 1 1 d . . . . .
C28 C 1.0097(4) 0.6299(3) 0.4942(3) 0.0261(10) Uani 1 1 d . . . . .
H28 H 1.0740 0.5821 0.4765 0.031 Uiso 1 1 calc R U . . .
C29 C 0.9808(3) 0.6531(3) 0.5849(3) 0.0246(8) Uani 1 1 d . . . . .
H29 H 1.0249 0.6202 0.6284 0.030 Uiso 1 1 calc R U . . .
C30 C 0.9809(5) 0.6505(4) 0.3287(3) 0.0504(14) Uani 1 1 d . . . . .
H30A H 0.9214 0.6757 0.2964 0.076 Uiso 1 1 calc R U . . .
H30B H 1.0053 0.5756 0.3289 0.076 Uiso 1 1 calc R U . . .
H30C H 1.0382 0.6844 0.2963 0.076 Uiso 1 1 calc R U . . .
C31 C 0.7565(3) 0.5071(3) 0.8166(3) 0.0263(8) Uani 1 1 d . . . . .
H31A H 0.7791 0.4399 0.7935 0.040 Uiso 1 1 calc R U . . .
H31B H 0.7448 0.4968 0.8850 0.040 Uiso 1 1 calc R U . . .
H31C H 0.8109 0.5468 0.7916 0.040 Uiso 1 1 calc R U . . .
C32 C 0.6543(3) 0.5663(2) 0.7850(2) 0.0165(7) Uani 1 1 d . . . . .
C33 C 0.5658(2) 0.5103(3) 0.8213(2) 0.0142(6) Uani 1 1 d . . . . .
C34 C 0.5775(3) 0.4124(3) 0.8734(2) 0.0188(7) Uani 1 1 d . . . . .
H34 H 0.6447 0.3759 0.8854 0.023 Uiso 1 1 calc R U . . .
C35 C 0.4918(3) 0.3688(3) 0.9075(2) 0.0200(7) Uani 1 1 d . . . . .
H35 H 0.4994 0.3021 0.9430 0.024 Uiso 1 1 calc R U . . .
C36 C 0.3945(3) 0.4230(3) 0.8898(2) 0.0185(7) Uani 1 1 d . . . . .
H36 H 0.3342 0.3944 0.9123 0.022 Uiso 1 1 calc R U . . .
C37 C 0.3875(3) 0.5202(3) 0.8381(2) 0.0157(6) Uani 1 1 d . . . . .
H37 H 0.3206 0.5582 0.8266 0.019 Uiso 1 1 calc R U . . .
C38 C 0.6200(3) 0.6698(3) 0.8265(2) 0.0189(7) Uani 1 1 d . . . . .
H38A H 0.5813 0.6588 0.8915 0.023 Uiso 1 1 calc R U . . .
H38B H 0.6829 0.6947 0.8275 0.023 Uiso 1 1 calc R U . . .
C39 C 0.5746(3) 0.8380(2) 0.7526(2) 0.0159(7) Uani 1 1 d . . . . .
H39 H 0.6300 0.8467 0.7782 0.019 Uiso 1 1 calc R U . . .
C40 C 0.5227(3) 0.9260(2) 0.6970(2) 0.0160(7) Uani 1 1 d . . . . .
C41 C 0.5451(3) 1.0226(3) 0.6966(3) 0.0217(7) Uani 1 1 d . . . . .
H41 H 0.5916 1.0277 0.7342 0.026 Uiso 1 1 calc R U . . .
C42 C 0.5007(3) 1.1098(3) 0.6427(3) 0.0252(8) Uani 1 1 d . . . . .
H42 H 0.5163 1.1745 0.6431 0.030 Uiso 1 1 calc R U . . .
C43 C 0.4324(3) 1.1015(3) 0.5876(3) 0.0239(8) Uani 1 1 d . . . . .
H43 H 0.4008 1.1614 0.5508 0.029 Uiso 1 1 calc R U . . .
C44 C 0.4102(3) 1.0080(3) 0.5857(2) 0.0198(7) Uani 1 1 d . . . . .
H44 H 0.3640 1.0045 0.5472 0.024 Uiso 1 1 calc R U . . .
C45 C 0.4548(3) 0.9169(2) 0.6400(2) 0.0152(6) Uani 1 1 d . . . . .
C46 C 0.6771(3) 0.5885(3) 0.6779(2) 0.0182(7) Uani 1 1 d . . . . .
H46A H 0.7212 0.6403 0.6584 0.022 Uiso 1 1 calc R U . . .
H46B H 0.7176 0.5243 0.6522 0.022 Uiso 1 1 calc R U . . .
C47 C 0.5877(3) 0.6091(2) 0.5550(2) 0.0176(7) Uani 1 1 d . . . . .
H47 H 0.6553 0.5796 0.5221 0.021 Uiso 1 1 calc R U . . .
C48 C 0.5007(3) 0.6299(3) 0.5073(2) 0.0149(7) Uani 1 1 d . . . . .
C49 C 0.5205(3) 0.6197(3) 0.4128(2) 0.0229(8) Uani 1 1 d . . . . .
H49 H 0.5911 0.6034 0.3802 0.027 Uiso 1 1 calc R U . . .
C50 C 0.4397(4) 0.6328(3) 0.3656(3) 0.0279(9) Uani 1 1 d . . . . .
H50 H 0.4543 0.6282 0.3006 0.033 Uiso 1 1 calc R U . . .
C51 C 0.3365(3) 0.6529(3) 0.4148(3) 0.0261(8) Uani 1 1 d . . . . .
H51 H 0.2804 0.6619 0.3828 0.031 Uiso 1 1 calc R U . . .
C52 C 0.3142(3) 0.6600(3) 0.5096(2) 0.0209(7) Uani 1 1 d . . . . .
H52 H 0.2432 0.6712 0.5421 0.025 Uiso 1 1 calc R U . . .
C53 C 0.3955(3) 0.6507(2) 0.5587(2) 0.0151(6) Uani 1 1 d . . . . .
C54 C 0.3023(2) 0.7692(2) 0.8873(2) 0.0140(6) Uani 1 1 d . . . . .
C55 C 0.2258(3) 0.7258(3) 0.9522(2) 0.0176(7) Uani 1 1 d . . . . .
H55 H 0.1952 0.6781 0.9343 0.021 Uiso 1 1 calc R U . . .
C56 C 0.1943(3) 0.7519(3) 1.0426(2) 0.0220(7) Uani 1 1 d . . . . .
H56 H 0.1414 0.7224 1.0849 0.026 Uiso 1 1 calc R U . . .
C57 C 0.2379(3) 0.8197(3) 1.0725(2) 0.0225(8) Uani 1 1 d . . . . .
C58 C 0.3124(3) 0.8635(3) 1.0070(3) 0.0203(8) Uani 1 1 d . . . . .
H58 H 0.3429 0.9111 1.0253 0.024 Uiso 1 1 calc R U . . .
C59 C 0.3437(3) 0.8403(3) 0.9166(2) 0.0176(7) Uani 1 1 d . . . . .
H59 H 0.3939 0.8730 0.8738 0.021 Uiso 1 1 calc R U . . .
C60 C 0.2067(4) 0.8440(3) 1.1716(3) 0.0385(11) Uani 1 1 d . . . . .
H60A H 0.2125 0.9147 1.1727 0.058 Uiso 1 1 calc R U . . .
H60B H 0.2533 0.7954 1.2097 0.058 Uiso 1 1 calc R U . . .
H60C H 0.1340 0.8378 1.1968 0.058 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
Al1 O3 1.814(2) . ?
Al1 O1 1.837(2) . ?
Al1 O2 1.843(2) . ?
Al1 N2 2.033(3) . ?
Al1 N3 2.071(3) . ?
Al1 N1 2.128(3) . ?
Al2 O6 1.811(2) . ?
Al2 O4 1.837(2) . ?
Al2 O5 1.844(2) . ?
Al2 N5 2.041(3) . ?
Al2 N6 2.066(3) . ?
Al2 N4 2.129(3) . ?
O1 C15 1.316(4) . ?
O2 C23 1.321(4) . ?
O3 C24 1.335(4) . ?
O4 C45 1.312(4) . ?
O5 C53 1.320(4) . ?
O6 C54 1.339(4) . ?
N1 C7 1.347(4) . ?
N1 C3 1.357(4) . ?
N2 C9 1.288(4) . ?
N2 C8 1.471(4) . ?
N3 C17 1.282(4) . ?
N3 C16 1.471(4) . ?
N4 C37 1.345(4) . ?
N4 C33 1.351(4) . ?
N5 C39 1.289(4) . ?
N5 C38 1.473(4) . ?
N6 C47 1.283(4) . ?
N6 C46 1.473(4) . ?
C1 C2 1.523(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.520(5) . ?
C2 C8 1.533(5) . ?
C2 C16 1.536(5) . ?
C3 C4 1.385(5) . ?
C4 C5 1.379(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(5) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.440(5) . ?
C9 H9 0.9500 . ?
C10 C15 1.402(5) . ?
C10 C11 1.411(5) . ?
C11 C12 1.368(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.386(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.373(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.413(5) . ?
C14 H14 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.435(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.403(5) . ?
C18 C23 1.418(5) . ?
C19 C20 1.368(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.401(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.386(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.407(5) . ?
C22 H22 0.9500 . ?
C24 C29 1.397(5) . ?
C24 C25 1.407(5) . ?
C25 C26 1.385(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.382(6) . ?
C26 H26 0.9500 . ?
C27 C28 1.396(6) . ?
C27 C30 1.511(5) . ?
C28 C29 1.384(5) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C32 1.529(5) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C33 1.512(4) . ?
C32 C46 1.536(5) . ?
C32 C38 1.549(5) . ?
C33 C34 1.394(5) . ?
C34 C35 1.376(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.381(5) . ?
C35 H35 0.9500 . ?
C36 C37 1.386(5) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.436(5) . ?
C39 H39 0.9500 . ?
C40 C41 1.410(5) . ?
C40 C45 1.419(5) . ?
C41 C42 1.377(5) . ?
C41 H41 0.9500 . ?
C42 C43 1.398(6) . ?
C42 H42 0.9500 . ?
C43 C44 1.375(5) . ?
C43 H43 0.9500 . ?
C44 C45 1.415(5) . ?
C44 H44 0.9500 . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 C48 1.444(5) . ?
C47 H47 0.9500 . ?
C48 C49 1.393(5) . ?
C48 C53 1.426(5) . ?
C49 C50 1.380(6) . ?
C49 H49 0.9500 . ?
C50 C51 1.393(6) . ?
C50 H50 0.9500 . ?
C51 C52 1.387(5) . ?
C51 H51 0.9500 . ?
C52 C53 1.414(5) . ?
C52 H52 0.9500 . ?
C54 C59 1.400(5) . ?
C54 C55 1.404(5) . ?
C55 C56 1.393(5) . ?
C55 H55 0.9500 . ?
C56 C57 1.386(5) . ?
C56 H56 0.9500 . ?
C57 C58 1.391(6) . ?
C57 C60 1.508(5) . ?
C58 C59 1.380(5) . ?
C58 H58 0.9500 . ?
C59 H59 0.9500 . ?
C60 H60A 0.9800 . ?
C60 H60B 0.9800 . ?
C60 H60C 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
O3 Al1 O1 96.79(11) . . ?
O3 Al1 O2 92.14(11) . . ?
O1 Al1 O2 91.34(11) . . ?
O3 Al1 N2 99.60(11) . . ?
O1 Al1 N2 89.26(12) . . ?
O2 Al1 N2 168.09(12) . . ?
O3 Al1 N3 167.14(11) . . ?
O1 Al1 N3 96.02(11) . . ?
O2 Al1 N3 86.39(11) . . ?
N2 Al1 N3 81.72(12) . . ?
O3 Al1 N1 87.69(11) . . ?
O1 Al1 N1 174.79(12) . . ?
O2 Al1 N1 91.15(11) . . ?
N2 Al1 N1 87.36(12) . . ?
N3 Al1 N1 79.57(10) . . ?
O6 Al2 O4 97.13(11) . . ?
O6 Al2 O5 91.45(11) . . ?
O4 Al2 O5 90.74(11) . . ?
O6 Al2 N5 100.02(11) . . ?
O4 Al2 N5 89.65(11) . . ?
O5 Al2 N5 168.38(12) . . ?
O6 Al2 N6 166.58(11) . . ?
O4 Al2 N6 96.22(11) . . ?
O5 Al2 N6 87.00(11) . . ?
N5 Al2 N6 81.41(11) . . ?
O6 Al2 N4 87.43(10) . . ?
O4 Al2 N4 175.10(11) . . ?
O5 Al2 N4 90.95(10) . . ?
N5 Al2 N4 87.77(11) . . ?
N6 Al2 N4 79.28(10) . . ?
C15 O1 Al1 130.2(2) . . ?
C23 O2 Al1 127.6(2) . . ?
C24 O3 Al1 137.9(2) . . ?
C45 O4 Al2 131.3(2) . . ?
C53 O5 Al2 126.4(2) . . ?
C54 O6 Al2 137.3(2) . . ?
C7 N1 C3 118.4(3) . . ?
C7 N1 Al1 117.1(2) . . ?
C3 N1 Al1 124.2(2) . . ?
C9 N2 C8 114.5(3) . . ?
C9 N2 Al1 124.5(2) . . ?
C8 N2 Al1 120.7(2) . . ?
C17 N3 C16 116.1(3) . . ?
C17 N3 Al1 123.3(2) . . ?
C16 N3 Al1 120.7(2) . . ?
C37 N4 C33 118.6(3) . . ?
C37 N4 Al2 117.1(2) . . ?
C33 N4 Al2 124.2(2) . . ?
C39 N5 C38 114.7(3) . . ?
C39 N5 Al2 124.7(2) . . ?
C38 N5 Al2 120.1(2) . . ?
C47 N6 C46 116.4(3) . . ?
C47 N6 Al2 123.1(2) . . ?
C46 N6 Al2 120.4(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 112.2(3) . . ?
C3 C2 C8 107.7(3) . . ?
C1 C2 C8 108.2(3) . . ?
C3 C2 C16 111.7(3) . . ?
C1 C2 C16 107.4(3) . . ?
C8 C2 C16 109.5(3) . . ?
N1 C3 C4 121.3(3) . . ?
N1 C3 C2 115.0(3) . . ?
C4 C3 C2 123.6(3) . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C7 118.2(3) . . ?
C5 C6 H6 120.9 . . ?
C7 C6 H6 120.9 . . ?
N1 C7 C6 122.9(3) . . ?
N1 C7 H7 118.5 . . ?
C6 C7 H7 118.5 . . ?
N2 C8 C2 111.4(3) . . ?
N2 C8 H8A 109.3 . . ?
C2 C8 H8A 109.3 . . ?
N2 C8 H8B 109.3 . . ?
C2 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
N2 C9 C10 125.3(3) . . ?
N2 C9 H9 117.3 . . ?
C10 C9 H9 117.3 . . ?
C15 C10 C11 120.2(3) . . ?
C15 C10 C9 121.7(3) . . ?
C11 C10 C9 118.0(3) . . ?
C12 C11 C10 121.3(4) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 118.4(4) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C14 C13 C12 121.9(4) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C13 C14 C15 120.6(4) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
O1 C15 C10 122.4(3) . . ?
O1 C15 C14 120.0(3) . . ?
C10 C15 C14 117.5(3) . . ?
N3 C16 C2 113.1(3) . . ?
N3 C16 H16A 109.0 . . ?
C2 C16 H16A 109.0 . . ?
N3 C16 H16B 109.0 . . ?
C2 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
N3 C17 C18 124.6(3) . . ?
N3 C17 H17 117.7 . . ?
C18 C17 H17 117.7 . . ?
C19 C18 C23 120.1(3) . . ?
C19 C18 C17 118.4(3) . . ?
C23 C18 C17 120.9(3) . . ?
C20 C19 C18 122.0(4) . . ?
C20 C19 H19 119.0 . . ?
C18 C19 H19 119.0 . . ?
C19 C20 C21 118.0(3) . . ?
C19 C20 H20 121.0 . . ?
C21 C20 H20 121.0 . . ?
C22 C21 C20 121.5(3) . . ?
C22 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C21 C22 C23 120.9(3) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
O2 C23 C22 120.3(3) . . ?
O2 C23 C18 122.3(3) . . ?
C22 C23 C18 117.4(3) . . ?
O3 C24 C29 122.5(3) . . ?
O3 C24 C25 120.4(3) . . ?
C29 C24 C25 117.0(3) . . ?
C26 C25 C24 121.1(3) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C27 C26 C25 121.8(4) . . ?
C27 C26 H26 119.1 . . ?
C25 C26 H26 119.1 . . ?
C26 C27 C28 117.3(3) . . ?
C26 C27 C30 121.8(4) . . ?
C28 C27 C30 120.9(4) . . ?
C29 C28 C27 121.6(4) . . ?
C29 C28 H28 119.2 . . ?
C27 C28 H28 119.2 . . ?
C28 C29 C24 121.1(4) . . ?
C28 C29 H29 119.4 . . ?
C24 C29 H29 119.4 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C32 C31 H31A 109.5 . . ?
C32 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C32 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C33 C32 C31 112.8(3) . . ?
C33 C32 C46 112.1(3) . . ?
C31 C32 C46 108.2(3) . . ?
C33 C32 C38 107.1(3) . . ?
C31 C32 C38 107.2(3) . . ?
C46 C32 C38 109.3(3) . . ?
N4 C33 C34 120.8(3) . . ?
N4 C33 C32 115.5(3) . . ?
C34 C33 C32 123.7(3) . . ?
C35 C34 C33 120.0(3) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C34 C35 C36 119.3(3) . . ?
C34 C35 H35 120.3 . . ?
C36 C35 H35 120.3 . . ?
C35 C36 C37 118.1(3) . . ?
C35 C36 H36 121.0 . . ?
C37 C36 H36 121.0 . . ?
N4 C37 C36 123.2(3) . . ?
N4 C37 H37 118.4 . . ?
C36 C37 H37 118.4 . . ?
N5 C38 C32 110.6(3) . . ?
N5 C38 H38A 109.5 . . ?
C32 C38 H38A 109.5 . . ?
N5 C38 H38B 109.5 . . ?
C32 C38 H38B 109.5 . . ?
H38A C38 H38B 108.1 . . ?
N5 C39 C40 125.4(3) . . ?
N5 C39 H39 117.3 . . ?
C40 C39 H39 117.3 . . ?
C41 C40 C45 120.0(3) . . ?
C41 C40 C39 118.0(3) . . ?
C45 C40 C39 121.9(3) . . ?
C42 C41 C40 121.2(4) . . ?
C42 C41 H41 119.4 . . ?
C40 C41 H41 119.4 . . ?
C41 C42 C43 118.9(3) . . ?
C41 C42 H42 120.5 . . ?
C43 C42 H42 120.5 . . ?
C44 C43 C42 121.1(4) . . ?
C44 C43 H43 119.5 . . ?
C42 C43 H43 119.5 . . ?
C43 C44 C45 121.4(4) . . ?
C43 C44 H44 119.3 . . ?
C45 C44 H44 119.3 . . ?
O4 C45 C44 120.3(3) . . ?
O4 C45 C40 122.3(3) . . ?
C44 C45 C40 117.4(3) . . ?
N6 C46 C32 113.1(3) . . ?
N6 C46 H46A 109.0 . . ?
C32 C46 H46A 109.0 . . ?
N6 C46 H46B 109.0 . . ?
C32 C46 H46B 109.0 . . ?
H46A C46 H46B 107.8 . . ?
N6 C47 C48 125.2(3) . . ?
N6 C47 H47 117.4 . . ?
C48 C47 H47 117.4 . . ?
C49 C48 C53 120.4(4) . . ?
C49 C48 C47 119.3(4) . . ?
C53 C48 C47 120.0(3) . . ?
C50 C49 C48 121.4(4) . . ?
C50 C49 H49 119.3 . . ?
C48 C49 H49 119.3 . . ?
C49 C50 C51 118.9(3) . . ?
C49 C50 H50 120.5 . . ?
C51 C50 H50 120.5 . . ?
C52 C51 C50 121.1(3) . . ?
C52 C51 H51 119.4 . . ?
C50 C51 H51 119.4 . . ?
C51 C52 C53 120.9(3) . . ?
C51 C52 H52 119.5 . . ?
C53 C52 H52 119.5 . . ?
O5 C53 C52 119.9(3) . . ?
O5 C53 C48 122.8(3) . . ?
C52 C53 C48 117.1(3) . . ?
O6 C54 C59 122.6(3) . . ?
O6 C54 C55 119.8(3) . . ?
C59 C54 C55 117.4(3) . . ?
C56 C55 C54 120.8(3) . . ?
C56 C55 H55 119.6 . . ?
C54 C55 H55 119.6 . . ?
C57 C56 C55 121.7(3) . . ?
C57 C56 H56 119.1 . . ?
C55 C56 H56 119.1 . . ?
C56 C57 C58 116.9(3) . . ?
C56 C57 C60 121.4(4) . . ?
C58 C57 C60 121.7(4) . . ?
C59 C58 C57 122.5(4) . . ?
C59 C58 H58 118.7 . . ?
C57 C58 H58 118.7 . . ?
C58 C59 C54 120.6(3) . . ?
C58 C59 H59 119.7 . . ?
C54 C59 H59 119.7 . . ?
C57 C60 H60A 109.5 . . ?
C57 C60 H60B 109.5 . . ?
H60A C60 H60B 109.5 . . ?
C57 C60 H60C 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?

_refine_diff_density_max         1.362
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.092

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_4FC6H4NCO_trimer
_database_code_depnum_ccdc_archive 'CCDC 1896211'
loop_
_audit_author_name
_audit_author_address
'Benjamin Ward'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2019-02-08 deposited with the CCDC.	2019-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H20 F3 N3 O4'
_chemical_formula_weight         483.44

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.5703(5)
_cell_length_b                   11.6337(5)
_cell_length_c                   14.6589(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.895(4)
_cell_angle_gamma                90
_cell_volume                     2286.41(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4646
_cell_measurement_theta_min      4.1690
_cell_measurement_theta_max      28.9360

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.333
_exptl_crystal_size_mid          0.324
_exptl_crystal_size_min          0.102
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.669
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45b (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5082
_diffrn_reflns_number            12060
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.314
_diffrn_reflns_theta_max         29.792
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.829
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.829
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5424
_reflns_number_gt                3939
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0440P)²+1.1611P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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_number_reflns         5424
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0703
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1233
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_restrained_S_all      0.987
_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
F1 F 0.25424(7) 0.20429(10) 0.55471(8) 0.0440(3) Uani 1 1 d . . . . .
F2 F 0.88271(9) 0.67717(10) 0.20351(8) 0.0490(3) Uani 1 1 d . . . . .
F3 F 1.07995(9) -0.13738(11) 0.69352(9) 0.0596(4) Uani 1 1 d . . . . .
O1 O 0.61451(8) 0.41483(11) 0.41349(8) 0.0334(3) Uani 1 1 d . . . . .
O2 O 0.93553(8) 0.29520(11) 0.48906(9) 0.0353(3) Uani 1 1 d . . . . .
O3 O 0.68654(9) 0.10581(11) 0.60215(8) 0.0353(3) Uani 1 1 d . . . . .
O4 O 0.78087(12) 0.45953(15) 0.63329(10) 0.0585(4) Uani 1 1 d . . . . .
N1 N 0.64771(9) 0.26091(12) 0.50885(9) 0.0278(3) Uani 1 1 d . . . . .
N2 N 0.77437(10) 0.34851(12) 0.44148(9) 0.0275(3) Uani 1 1 d . . . . .
N3 N 0.81269(10) 0.19555(12) 0.54454(9) 0.0287(3) Uani 1 1 d . . . . .
C1 C 0.67400(12) 0.34744(15) 0.45205(11) 0.0273(3) Uani 1 1 d . . . . .
C2 C 0.54349(12) 0.24935(15) 0.51885(11) 0.0284(4) Uani 1 1 d . . . . .
C3 C 0.50222(13) 0.32295(16) 0.57589(13) 0.0348(4) Uani 1 1 d . . . . .
H3 H 0.5412 0.3831 0.6070 0.042 Uiso 1 1 calc R U . . .
C4 C 0.40342(13) 0.30896(17) 0.58778(13) 0.0368(4) Uani 1 1 d . . . . .
H4 H 0.3732 0.3592 0.6265 0.044 Uiso 1 1 calc R U . . .
C5 C 0.35096(12) 0.22038(16) 0.54189(13) 0.0330(4) Uani 1 1 d . . . . .
C6 C 0.38943(13) 0.14639(17) 0.48347(13) 0.0369(4) Uani 1 1 d . . . . .
H6 H 0.3500 0.0868 0.4521 0.044 Uiso 1 1 calc R U . . .
C7 C 0.48823(13) 0.16205(16) 0.47191(12) 0.0339(4) Uani 1 1 d . . . . .
H7 H 0.5177 0.1129 0.4319 0.041 Uiso 1 1 calc R U . . .
C8 C 0.84768(12) 0.28168(15) 0.49202(11) 0.0285(4) Uani 1 1 d . . . . .
C9 C 0.80496(12) 0.43419(14) 0.37990(11) 0.0272(3) Uani 1 1 d . . . . .
C10 C 0.79386(14) 0.41039(17) 0.28669(12) 0.0377(4) Uani 1 1 d . . . . .
H10 H 0.7684 0.3381 0.2638 0.045 Uiso 1 1 calc R U . . .
C11 C 0.82026(15) 0.49307(18) 0.22669(12) 0.0421(5) Uani 1 1 d . . . . .
H11 H 0.8128 0.4788 0.1622 0.050 Uiso 1 1 calc R U . . .
C12 C 0.85721(13) 0.59547(16) 0.26262(12) 0.0343(4) Uani 1 1 d . . . . .
C13 C 0.87073(13) 0.62031(16) 0.35495(13) 0.0363(4) Uani 1 1 d . . . . .
H13 H 0.8978 0.6920 0.3775 0.044 Uiso 1 1 calc R U . . .
C14 C 0.84359(13) 0.53743(16) 0.41472(12) 0.0332(4) Uani 1 1 d . . . . .
H14 H 0.8516 0.5520 0.4792 0.040 Uiso 1 1 calc R U . . .
C15 C 0.71326(12) 0.18188(15) 0.55572(11) 0.0282(4) Uani 1 1 d . . . . .
C16 C 0.88211(12) 0.10919(15) 0.58593(11) 0.0287(4) Uani 1 1 d . . . . .
C17 C 0.94890(13) 0.13324(17) 0.66440(12) 0.0367(4) Uani 1 1 d . . . . .
H17 H 0.9490 0.2066 0.6929 0.044 Uiso 1 1 calc R U . . .
C18 C 1.01600(14) 0.04908(19) 0.70131(13) 0.0425(5) Uani 1 1 d . . . . .
H18 H 1.0633 0.0640 0.7549 0.051 Uiso 1 1 calc R U . . .
C19 C 1.01236(14) -0.05585(18) 0.65869(13) 0.0401(4) Uani 1 1 d . . . . .
C20 C 0.94498(13) -0.08309(16) 0.58222(13) 0.0372(4) Uani 1 1 d . . . . .
H20 H 0.9432 -0.1577 0.5556 0.045 Uiso 1 1 calc R U . . .
C21 C 0.87959(12) 0.00191(16) 0.54518(12) 0.0328(4) Uani 1 1 d . . . . .
H21 H 0.8327 -0.0135 0.4915 0.039 Uiso 1 1 calc R U . . .
C22 C 0.72487(17) 0.5561(2) 0.65627(18) 0.0586(6) Uani 1 1 d . . . . .
H22A H 0.6955 0.5405 0.7128 0.070 Uiso 1 1 calc R U . . .
H22B H 0.6704 0.5741 0.6052 0.070 Uiso 1 1 calc R U . . .
C23 C 0.79801(18) 0.6545(2) 0.67205(16) 0.0573(6) Uani 1 1 d . . . . .
H23A H 0.7828 0.7052 0.7224 0.069 Uiso 1 1 calc R U . . .
H23B H 0.7967 0.7008 0.6152 0.069 Uiso 1 1 calc R U . . .
C24 C 0.89875(17) 0.5958(2) 0.69868(16) 0.0578(6) Uani 1 1 d . . . . .
H24A H 0.9451 0.6169 0.6555 0.069 Uiso 1 1 calc R U . . .
H24B H 0.9293 0.6169 0.7622 0.069 Uiso 1 1 calc R U . . .
C25 C 0.87426(19) 0.4701(2) 0.69223(19) 0.0663(7) Uani 1 1 d . . . . .
H25A H 0.9266 0.4274 0.6663 0.080 Uiso 1 1 calc R U . . .
H25B H 0.8696 0.4386 0.7542 0.080 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
F1 C5 1.3672(19) . ?
F2 C12 1.366(2) . ?
F3 C19 1.363(2) . ?
O1 C1 1.202(2) . ?
O2 C8 1.2099(19) . ?
O3 C15 1.206(2) . ?
O4 C25 1.425(3) . ?
O4 C22 1.426(3) . ?
N1 C15 1.386(2) . ?
N1 C1 1.388(2) . ?
N1 C2 1.451(2) . ?
N2 C8 1.384(2) . ?
N2 C1 1.395(2) . ?
N2 C9 1.448(2) . ?
N3 C8 1.391(2) . ?
N3 C15 1.393(2) . ?
N3 C16 1.445(2) . ?
C2 C3 1.375(2) . ?
C2 C7 1.381(2) . ?
C3 C4 1.388(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.369(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.373(3) . ?
C6 C7 1.389(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C9 C14 1.377(2) . ?
C9 C10 1.379(2) . ?
C10 C11 1.387(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.366(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.368(3) . ?
C13 C14 1.390(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C16 C17 1.379(2) . ?
C16 C21 1.382(2) . ?
C17 C18 1.389(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.369(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.370(3) . ?
C20 C21 1.382(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.510(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.524(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.499(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C25 O4 C22 104.21(17) . . ?
C15 N1 C1 125.04(14) . . ?
C15 N1 C2 116.71(13) . . ?
C1 N1 C2 118.23(13) . . ?
C8 N2 C1 124.69(14) . . ?
C8 N2 C9 117.96(13) . . ?
C1 N2 C9 117.03(13) . . ?
C8 N3 C15 124.54(14) . . ?
C8 N3 C16 118.49(13) . . ?
C15 N3 C16 116.84(13) . . ?
O1 C1 N1 122.62(15) . . ?
O1 C1 N2 122.58(15) . . ?
N1 C1 N2 114.79(14) . . ?
C3 C2 C7 121.34(16) . . ?
C3 C2 N1 119.92(15) . . ?
C7 C2 N1 118.72(15) . . ?
C2 C3 C4 119.69(17) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 117.76(17) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
F1 C5 C4 118.23(16) . . ?
F1 C5 C6 117.75(16) . . ?
C4 C5 C6 124.02(16) . . ?
C5 C6 C7 117.46(16) . . ?
C5 C6 H6 121.3 . . ?
C7 C6 H6 121.3 . . ?
C2 C7 C6 119.71(16) . . ?
C2 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
O2 C8 N2 122.58(15) . . ?
O2 C8 N3 122.41(15) . . ?
N2 C8 N3 114.98(14) . . ?
C14 C9 C10 121.30(16) . . ?
C14 C9 N2 119.92(15) . . ?
C10 C9 N2 118.78(15) . . ?
C9 C10 C11 119.30(17) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 118.39(17) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C11 C12 F2 118.42(16) . . ?
C11 C12 C13 123.42(17) . . ?
F2 C12 C13 118.16(17) . . ?
C12 C13 C14 117.96(17) . . ?
C12 C13 H13 121.0 . . ?
C14 C13 H13 121.0 . . ?
C9 C14 C13 119.62(16) . . ?
C9 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
O3 C15 N1 122.75(15) . . ?
O3 C15 N3 122.09(15) . . ?
N1 C15 N3 115.15(14) . . ?
C17 C16 C21 120.88(16) . . ?
C17 C16 N3 120.73(16) . . ?
C21 C16 N3 118.40(14) . . ?
C16 C17 C18 119.27(18) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C19 C18 C17 118.40(17) . . ?
C19 C18 H18 120.8 . . ?
C17 C18 H18 120.8 . . ?
F3 C19 C18 118.36(17) . . ?
F3 C19 C20 118.10(18) . . ?
C18 C19 C20 123.53(18) . . ?
C19 C20 C21 117.56(18) . . ?
C19 C20 H20 121.2 . . ?
C21 C20 H20 121.2 . . ?
C16 C21 C20 120.32(16) . . ?
C16 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
O4 C22 C23 105.79(18) . . ?
O4 C22 H22A 110.6 . . ?
C23 C22 H22A 110.6 . . ?
O4 C22 H22B 110.6 . . ?
C23 C22 H22B 110.6 . . ?
H22A C22 H22B 108.7 . . ?
C22 C23 C24 104.0(2) . . ?
C22 C23 H23A 111.0 . . ?
C24 C23 H23A 111.0 . . ?
C22 C23 H23B 111.0 . . ?
C24 C23 H23B 111.0 . . ?
H23A C23 H23B 109.0 . . ?
C25 C24 C23 103.89(19) . . ?
C25 C24 H24A 111.0 . . ?
C23 C24 H24A 111.0 . . ?
C25 C24 H24B 111.0 . . ?
C23 C24 H24B 111.0 . . ?
H24A C24 H24B 109.0 . . ?
O4 C25 C24 106.9(2) . . ?
O4 C25 H25A 110.3 . . ?
C24 C25 H25A 110.3 . . ?
O4 C25 H25B 110.3 . . ?
C24 C25 H25B 110.3 . . ?
H25A C25 H25B 108.6 . . ?

_refine_diff_density_max         0.200
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1896207'
loop_
_audit_author_name
_audit_author_address
'Benjamin Ward'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2019-02-08 deposited with the CCDC.	2019-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H30 Al N3 O2'
_chemical_formula_weight         491.55

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'
Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   8.9816(6)
_cell_length_b                   10.2889(7)
_cell_length_c                   14.1189(10)
_cell_angle_alpha                71.196(3)
_cell_angle_beta                 84.480(3)
_cell_angle_gamma                88.775(3)
_cell_volume                     1229.31(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    27652
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.098
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.643
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            26329
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.091
_diffrn_reflns_theta_max         27.544
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5623
_reflns_number_gt                5393
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0592P)²+0.5031P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5623
_refine_ls_number_parameters     327
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1063
_refine_ls_wR_factor_gt          0.1052
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_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
Al1 Al 0.59608(4) 0.31863(3) 0.29378(2) 0.01814(10) Uani 1 1 d . . . . .
O1 O 0.72053(9) 0.35124(8) 0.17579(6) 0.02216(17) Uani 1 1 d . . . . .
N2 N 0.56614(10) 0.12013(9) 0.29021(7) 0.02028(19) Uani 1 1 d . . . . .
O2 O 0.59249(9) 0.50517(8) 0.27649(6) 0.02043(17) Uani 1 1 d . . . . .
N1 N 0.42226(11) 0.27504(10) 0.41450(7) 0.02074(19) Uani 1 1 d . . . . .
C1 C 0.15404(13) 0.04127(12) 0.35580(9) 0.0260(2) Uani 1 1 d . . . . .
H1A H 0.1532 0.0047 0.2998 0.039 Uiso 1 1 calc R U . . .
H1B H 0.0643 0.0962 0.3586 0.039 Uiso 1 1 calc R U . . .
H1C H 0.1554 -0.0349 0.4189 0.039 Uiso 1 1 calc R U . . .
C2 C 0.29372(12) 0.13171(11) 0.34017(8) 0.0213(2) Uani 1 1 d . . . . .
C3 C 0.29805(13) 0.19933(11) 0.42126(8) 0.0217(2) Uani 1 1 d . . . . .
N3 N 0.40713(10) 0.35011(10) 0.21646(7) 0.01989(19) Uani 1 1 d . . . . .
C4 C 0.18599(14) 0.18318(13) 0.49979(9) 0.0281(3) Uani 1 1 d . . . . .
H4 H 0.0994 0.1294 0.5039 0.034 Uiso 1 1 calc R U . . .
C5 C 0.20129(15) 0.24591(13) 0.57191(10) 0.0313(3) Uani 1 1 d . . . . .
H5 H 0.1256 0.2353 0.6258 0.038 Uiso 1 1 calc R U . . .
C6 C 0.32826(15) 0.32426(13) 0.56442(9) 0.0295(3) Uani 1 1 d . . . . .
H6 H 0.3414 0.3686 0.6126 0.035 Uiso 1 1 calc R U . . .
C7 C 0.43523(14) 0.33593(12) 0.48469(9) 0.0248(2) Uani 1 1 d . . . . .
H7 H 0.5223 0.3897 0.4792 0.030 Uiso 1 1 calc R U . . .
C8 C 0.43261(12) 0.03949(11) 0.34308(9) 0.0226(2) Uani 1 1 d . . . . .
H8A H 0.4508 -0.0087 0.4139 0.027 Uiso 1 1 calc R U . . .
H8B H 0.4132 -0.0307 0.3114 0.027 Uiso 1 1 calc R U . . .
C9 C 0.66285(13) 0.06039(11) 0.24510(9) 0.0222(2) Uani 1 1 d . . . . .
H9 H 0.6441 -0.0329 0.2520 0.027 Uiso 1 1 calc R U . . .
C10 C 0.79712(12) 0.12350(11) 0.18497(8) 0.0213(2) Uani 1 1 d . . . . .
C11 C 0.90375(13) 0.04095(12) 0.15212(9) 0.0242(2) Uani 1 1 d . . . . .
H11 H 0.8879 -0.0556 0.1729 0.029 Uiso 1 1 calc R U . . .
C12 C 1.03060(13) 0.09713(13) 0.09054(9) 0.0260(2) Uani 1 1 d . . . . .
H12 H 1.1019 0.0401 0.0695 0.031 Uiso 1 1 calc R U . . .
C13 C 1.05266(13) 0.23978(13) 0.05941(9) 0.0251(2) Uani 1 1 d . . . . .
H13 H 1.1396 0.2796 0.0169 0.030 Uiso 1 1 calc R U . . .
C14 C 0.94944(13) 0.32290(12) 0.08977(8) 0.0235(2) Uani 1 1 d . . . . .
H14 H 0.9669 0.4192 0.0679 0.028 Uiso 1 1 calc R U . . .
C15 C 0.81852(12) 0.26841(11) 0.15257(8) 0.0202(2) Uani 1 1 d . . . . .
C24 C 0.74968(13) 0.25554(12) 0.39486(9) 0.0239(2) Uani 1 1 d . . . . .
H24A H 0.7185 0.1666 0.4440 0.036 Uiso 1 1 calc R U . . .
H24B H 0.7578 0.3232 0.4296 0.036 Uiso 1 1 calc R U . . .
H24C H 0.8470 0.2463 0.3599 0.036 Uiso 1 1 calc R U . . .
C23 C 0.57346(12) 0.60124(11) 0.19066(8) 0.0195(2) Uani 1 1 d . . . . .
C22 C 0.64493(13) 0.73040(11) 0.16625(8) 0.0219(2) Uani 1 1 d . . . . .
H22 H 0.7087 0.7460 0.2115 0.026 Uiso 1 1 calc R U . . .
C21 C 0.62425(13) 0.83460(11) 0.07800(9) 0.0241(2) Uani 1 1 d . . . . .
H21 H 0.6736 0.9204 0.0640 0.029 Uiso 1 1 calc R U . . .
C20 C 0.53206(14) 0.81582(12) 0.00907(9) 0.0263(2) Uani 1 1 d . . . . .
H20 H 0.5195 0.8875 -0.0518 0.032 Uiso 1 1 calc R U . . .
C19 C 0.45960(14) 0.69107(12) 0.03113(9) 0.0254(2) Uani 1 1 d . . . . .
H19 H 0.3960 0.6775 -0.0149 0.030 Uiso 1 1 calc R U . . .
C18 C 0.47841(13) 0.58367(11) 0.12073(8) 0.0218(2) Uani 1 1 d . . . . .
C17 C 0.38670(13) 0.46171(12) 0.14485(8) 0.0225(2) Uani 1 1 d . . . . .
H17 H 0.3062 0.4641 0.1053 0.027 Uiso 1 1 calc R U . . .
C16 C 0.29341(13) 0.24132(12) 0.23566(9) 0.0228(2) Uani 1 1 d . . . . .
H16A H 0.3109 0.1958 0.1836 0.027 Uiso 1 1 calc R U . . .
H16B H 0.1934 0.2839 0.2293 0.027 Uiso 1 1 calc R U . . .
C25 C 0.0393(2) 0.5325(2) 0.3264(2) 0.0717(7) Uani 1 1 d . U . . .
H25 H -0.0211 0.4544 0.3627 0.086 Uiso 1 1 calc R U . . .
C26 C 0.1451(2) 0.57753(18) 0.37305(15) 0.0546(4) Uani 1 1 d . U . . .
H26 H 0.1568 0.5315 0.4420 0.065 Uiso 1 1 calc R U . . .
C27 C 0.23349(17) 0.68864(15) 0.32026(11) 0.0376(3) Uani 1 1 d . U . . .
H27 H 0.3067 0.7194 0.3527 0.045 Uiso 1 1 calc R U . . .
C28 C 0.21739(18) 0.75583(15) 0.22116(11) 0.0391(3) Uani 1 1 d . U . . .
H28 H 0.2803 0.8323 0.1851 0.047 Uiso 1 1 calc R U . . .
C29 C 0.1112(2) 0.7138(2) 0.17338(14) 0.0550(5) Uani 1 1 d . U . . .
H29 H 0.0998 0.7617 0.1047 0.066 Uiso 1 1 calc R U . . .
C30 C 0.0207(2) 0.6015(2) 0.2256(2) 0.0693(7) Uani 1 1 d . U . . .
H30 H -0.0532 0.5718 0.1931 0.083 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
Al1 O1 1.8533(9) . ?
Al1 O2 1.8550(8) . ?
Al1 C24 2.0260(12) . ?
Al1 N3 2.0692(10) . ?
Al1 N2 2.0829(10) . ?
Al1 N1 2.1375(10) . ?
O1 C15 1.3041(13) . ?
N2 C9 1.2888(15) . ?
N2 C8 1.4680(14) . ?
O2 C23 1.3172(13) . ?
N1 C7 1.3468(15) . ?
N1 C3 1.3524(14) . ?
C1 C2 1.5338(15) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.5231(15) . ?
C2 C16 1.5418(16) . ?
C2 C8 1.5467(16) . ?
C3 C4 1.3942(16) . ?
N3 C17 1.2855(15) . ?
N3 C16 1.4730(14) . ?
C4 C5 1.3880(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3865(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.3836(17) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.4415(15) . ?
C9 H9 0.9500 . ?
C10 C11 1.4098(15) . ?
C10 C15 1.4229(15) . ?
C11 C12 1.3790(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.4023(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3786(16) . ?
C13 H13 0.9500 . ?
C14 C15 1.4108(15) . ?
C14 H14 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C23 C22 1.4126(15) . ?
C23 C18 1.4213(15) . ?
C22 C21 1.3824(16) . ?
C22 H22 0.9500 . ?
C21 C20 1.3976(17) . ?
C21 H21 0.9500 . ?
C20 C19 1.3809(17) . ?
C20 H20 0.9500 . ?
C19 C18 1.4078(16) . ?
C19 H19 0.9500 . ?
C18 C17 1.4436(16) . ?
C17 H17 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C25 C26 1.374(3) . ?
C25 C30 1.395(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.367(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.367(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.371(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.384(3) . ?
C29 H29 0.9500 . ?
C30 H30 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
O1 Al1 O2 90.30(4) . . ?
O1 Al1 C24 99.56(4) . . ?
O2 Al1 C24 100.50(4) . . ?
O1 Al1 N3 91.67(4) . . ?
O2 Al1 N3 86.78(4) . . ?
C24 Al1 N3 166.52(5) . . ?
O1 Al1 N2 87.38(4) . . ?
O2 Al1 N2 167.52(4) . . ?
C24 Al1 N2 91.99(4) . . ?
N3 Al1 N2 81.03(4) . . ?
O1 Al1 N1 169.76(4) . . ?
O2 Al1 N1 92.44(4) . . ?
C24 Al1 N1 89.64(4) . . ?
N3 Al1 N1 78.65(4) . . ?
N2 Al1 N1 87.82(4) . . ?
C15 O1 Al1 127.63(7) . . ?
C9 N2 C8 116.65(9) . . ?
C9 N2 Al1 122.97(8) . . ?
C8 N2 Al1 120.35(7) . . ?
C23 O2 Al1 124.14(7) . . ?
C7 N1 C3 118.72(10) . . ?
C7 N1 Al1 116.30(8) . . ?
C3 N1 Al1 124.84(8) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 112.51(9) . . ?
C3 C2 C16 110.56(9) . . ?
C1 C2 C16 107.24(9) . . ?
C3 C2 C8 108.57(9) . . ?
C1 C2 C8 107.94(9) . . ?
C16 C2 C8 109.98(9) . . ?
N1 C3 C4 120.86(11) . . ?
N1 C3 C2 115.35(9) . . ?
C4 C3 C2 123.77(10) . . ?
C17 N3 C16 116.09(9) . . ?
C17 N3 Al1 122.23(8) . . ?
C16 N3 Al1 121.53(7) . . ?
C5 C4 C3 119.78(11) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C6 C5 C4 119.24(11) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C7 C6 C5 118.02(11) . . ?
C7 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
N1 C7 C6 123.38(11) . . ?
N1 C7 H7 118.3 . . ?
C6 C7 H7 118.3 . . ?
N2 C8 C2 111.45(9) . . ?
N2 C8 H8A 109.3 . . ?
C2 C8 H8A 109.3 . . ?
N2 C8 H8B 109.3 . . ?
C2 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
N2 C9 C10 125.37(10) . . ?
N2 C9 H9 117.3 . . ?
C10 C9 H9 117.3 . . ?
C11 C10 C15 119.62(10) . . ?
C11 C10 C9 119.22(10) . . ?
C15 C10 C9 121.01(10) . . ?
C12 C11 C10 121.48(11) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 118.97(11) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C14 C13 C12 120.69(11) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 121.62(11) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
O1 C15 C14 119.61(10) . . ?
O1 C15 C10 122.74(10) . . ?
C14 C15 C10 117.61(10) . . ?
Al1 C24 H24A 109.5 . . ?
Al1 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
Al1 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O2 C23 C22 120.07(10) . . ?
O2 C23 C18 122.94(10) . . ?
C22 C23 C18 116.96(10) . . ?
C21 C22 C23 121.52(11) . . ?
C21 C22 H22 119.2 . . ?
C23 C22 H22 119.2 . . ?
C22 C21 C20 121.13(11) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C19 C20 C21 118.75(11) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 H20 120.6 . . ?
C20 C19 C18 121.12(11) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C18 C23 120.52(10) . . ?
C19 C18 C17 118.36(10) . . ?
C23 C18 C17 120.77(10) . . ?
N3 C17 C18 124.09(10) . . ?
N3 C17 H17 118.0 . . ?
C18 C17 H17 118.0 . . ?
N3 C16 C2 113.57(9) . . ?
N3 C16 H16A 108.9 . . ?
C2 C16 H16A 108.9 . . ?
N3 C16 H16B 108.9 . . ?
C2 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C26 C25 C30 119.94(18) . . ?
C26 C25 H25 120.0 . . ?
C30 C25 H25 120.0 . . ?
C27 C26 C25 119.95(19) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C28 C27 C26 120.51(16) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C27 C28 C29 120.55(16) . . ?
C27 C28 H28 119.7 . . ?
C29 C28 H28 119.7 . . ?
C28 C29 C30 119.77(18) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C29 C30 C25 119.27(16) . . ?
C29 C30 H30 120.4 . . ?
C25 C30 H30 120.4 . . ?

_refine_diff_density_max         0.383
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_4CF3C6H4NCO_trimer
_database_code_depnum_ccdc_archive 'CCDC 1896212'
loop_
_audit_author_name
_audit_author_address
'Benjamin Ward'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2019-02-08 deposited with the CCDC.	2019-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H12 F9 N3 O3'
_chemical_formula_weight         561.37

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c :H'
_space_group_name_Hall           '-R 3 2"c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'

_cell_length_a                   16.3987(7)
_cell_length_b                   16.3987(7)
_cell_length_c                   18.1743(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4232.6(5)
_cell_formula_units_Z            6
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2147
_cell_measurement_theta_min      3.9210
_cell_measurement_theta_max      28.2150

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             1692
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.291
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.164
_exptl_absorpt_coefficient_mu    0.128
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.669
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45b (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5082
_diffrn_reflns_number            7152
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.958
_diffrn_reflns_theta_max         29.534
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1238
_reflns_number_gt                851
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The structure contained highly disordered solvent, probably THF with the
oxygen atom lying on a spcial position and the remaining carbons disordered
around the 3-fold axis. After exhaustive attempts to model the disorder
were unsuccessful, the solvent was instead modelled using SQUEEZE.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1529P)²+4.7980P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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_number_reflns         1238
_refine_ls_number_parameters     76
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0781
_refine_ls_wR_factor_ref         0.2951
_refine_ls_wR_factor_gt          0.2686
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_restrained_S_all      1.405
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

# SQUEEZE RESULTS (Version = 241018)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.000 104 22 ' '
2 0.000 0.000 0.500 104 22 ' '
3 0.333 0.667 0.667 104 22 ' '
4 0.333 0.667 0.167 104 22 ' '
5 0.667 0.333 0.333 105 22 ' '
6 0.667 0.333 0.833 105 22 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.5320(3) 0.5537(4) 0.6710(3) 0.1182(18) Uani 0.5 1 d D U P . .
F2 F 0.5921(5) 0.4966(4) 0.7452(4) 0.128(2) Uani 0.5 1 d D U P . .
F3 F 0.5108(5) 0.5570(5) 0.7888(4) 0.158(3) Uani 0.5 1 d D U P . .
O1 O 0.84005(14) 1.0000 0.7500 0.0635(8) Uani 1 2 d S T P . .
N1 N 0.91725(14) 0.91725(14) 0.7500 0.0463(7) Uani 1 2 d S T P . .
C1 C 0.91343(17) 1.0000 0.7500 0.0466(8) Uani 1 2 d S T P . .
C2 C 0.82888(18) 0.82888(18) 0.7500 0.0478(8) Uani 1 2 d S T P . .
C3 C 0.80636(19) 0.76932(19) 0.69058(15) 0.0612(8) Uani 1 1 d . . . . .
H3 H 0.8479 0.7861 0.6498 0.073 Uiso 1 1 calc R U . . .
C4 C 0.7226(2) 0.6850(2) 0.6912(2) 0.0767(10) Uani 1 1 d . . . . .
H4 H 0.7066 0.6426 0.6510 0.092 Uiso 1 1 calc R U . . .
C5 C 0.6623(2) 0.6623(2) 0.7500 0.0793(13) Uani 1 2 d S T P . .
C6 C 0.5709(4) 0.5709(4) 0.7500 0.125(2) Uani 1 2 d DS TU 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
F1 F3 1.220(11) 4_556 ?
F1 C6 1.540(5) . ?
F2 F3 0.948(10) 4_556 ?
F2 C6 1.426(6) . ?
F3 F2 0.948(10) 4_556 ?
F3 C6 1.139(7) . ?
F3 F1 1.220(11) 4_556 ?
O1 C1 1.203(4) . ?
N1 C1 1.3893(18) 2_765 ?
N1 C1 1.3893(18) . ?
N1 C2 1.449(4) . ?
C1 N1 1.3893(18) 3_675 ?
C2 C3 1.377(3) . ?
C2 C3 1.377(3) 4_556 ?
C3 C4 1.378(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.375(4) . ?
C4 H4 0.9500 . ?
C5 C4 1.375(4) 4_556 ?
C5 C6 1.499(7) . ?
C6 F3 1.139(7) 4_556 ?
C6 F2 1.426(6) 4_556 ?
C6 F1 1.540(5) 4_556 ?

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
F3 F1 C6 47.0(4) 4_556 . ?
F3 F2 C6 52.8(6) 4_556 . ?
F2 F3 C6 85.7(6) 4_556 . ?
F2 F3 F1 162.1(9) 4_556 4_556 ?
C6 F3 F1 81.4(7) . 4_556 ?
C1 N1 C1 124.5(3) 2_765 . ?
C1 N1 C2 117.76(13) 2_765 . ?
C1 N1 C2 117.76(13) . . ?
O1 C1 N1 122.24(13) . . ?
O1 C1 N1 122.24(13) . 3_675 ?
N1 C1 N1 115.5(3) . 3_675 ?
C3 C2 C3 121.5(3) . 4_556 ?
C3 C2 N1 119.26(16) . . ?
C3 C2 N1 119.26(16) 4_556 . ?
C2 C3 C4 119.0(3) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C4 120.7(4) 4_556 . ?
C4 C5 C6 119.65(18) 4_556 . ?
C4 C5 C6 119.65(18) . . ?
F3 C6 F3 115.6(9) 4_556 . ?
F3 C6 F2 41.5(5) 4_556 . ?
F3 C6 F2 115.0(6) . . ?
F3 C6 F2 115.0(6) 4_556 4_556 ?
F3 C6 F2 41.5(5) . 4_556 ?
F2 C6 F2 144.4(7) . 4_556 ?
F3 C6 C5 122.2(4) 4_556 . ?
F3 C6 C5 122.2(4) . . ?
F2 C6 C5 107.8(4) . . ?
F2 C6 C5 107.8(4) 4_556 . ?
F3 C6 F1 51.6(5) 4_556 . ?
F3 C6 F1 107.6(5) . . ?
F2 C6 F1 92.4(4) . . ?
F2 C6 F1 77.0(3) 4_556 . ?
C5 C6 F1 107.4(3) . . ?
F3 C6 F1 107.6(5) 4_556 4_556 ?
F3 C6 F1 51.6(5) . 4_556 ?
F2 C6 F1 77.0(3) . 4_556 ?
F2 C6 F1 92.4(4) 4_556 4_556 ?
C5 C6 F1 107.4(3) . 4_556 ?
F1 C6 F1 145.2(6) . 4_556 ?

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.051


####################################################################### 
# 
# 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_4MeOC6H4NCO_trimer
_database_code_depnum_ccdc_archive 'CCDC 1896213'
loop_
_audit_author_name
_audit_author_address
'Benjamin Ward'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2019-02-08 deposited with the CCDC.	2019-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H21 N3 O6'
_chemical_formula_weight         447.44

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'

_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c :H'
_space_group_name_Hall           'R 3 -2"c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   13.1448(5)
_cell_length_b                   13.1448(5)
_cell_length_c                   26.2723(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3931.3(3)
_cell_formula_units_Z            6
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3697
_cell_measurement_theta_min      4.7090
_cell_measurement_theta_max      28.5020

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_F_000             1404
_exptl_transmission_factor_min   4.7090
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.283
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.195
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.508
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45b (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5082
_diffrn_reflns_number            6859
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         3.581
_diffrn_reflns_theta_max         29.706
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2162
_reflns_number_gt                1950
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.873
_reflns_Friedel_fraction_max     0.815
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The structure contained highly disordered solvent, probably THF with the
oxygen atom lying on a spcial position and the remaining carbons disordered
around the 3-fold axis. After exhaustive attempts to model the disorder
were unsuccessful, the solvent was instead modelled using SQUEEZE.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0699P)²+1.8930P] 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 847 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2162
_refine_ls_number_parameters     101
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1346
_refine_ls_wR_factor_gt          0.1304
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.003

# SQUEEZE RESULTS (Version = 241018)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.106 10 2 ' '
2 0.000 0.000 0.323 141 35 ' '
3 0.000 0.000 0.606 10 2 ' '
4 0.000 0.000 0.823 141 35 ' '
5 0.333 0.667 0.489 146 35 ' '
6 0.333 0.667 0.989 146 35 ' '
7 0.333 0.667 0.273 13 2 ' '
8 0.333 0.667 0.773 13 2 ' '
9 0.667 0.333 0.156 138 34 ' '
10 0.667 0.333 0.656 138 34 ' '
11 0.667 0.333 0.440 13 2 ' '
12 0.667 0.333 0.940 13 2 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?

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 1.04592(17) 0.82708(16) 0.49422(9) 0.0476(5) Uani 1 1 d . . . . .
O2 O 0.5374(2) 0.4261(2) 0.49838(12) 0.0767(8) Uani 1 1 d . . . . .
N1 N 0.91109(16) 0.88716(16) 0.49670(8) 0.0359(5) Uani 1 1 d . . . . .
C1 C 1.0249(2) 0.9059(2) 0.49557(10) 0.0370(5) Uani 1 1 d . . . . .
C2 C 0.8145(2) 0.7663(2) 0.49905(11) 0.0380(5) Uani 1 1 d . . . . .
C3 C 0.7860(3) 0.6955(3) 0.45593(12) 0.0510(7) Uani 1 1 d . . . . .
H3 H 0.8300 0.7252 0.4255 0.061 Uiso 1 1 calc R U . . .
C4 C 0.6929(3) 0.5815(3) 0.45797(13) 0.0617(9) Uani 1 1 d . . . . .
H4 H 0.6736 0.5320 0.4290 0.074 Uiso 1 1 calc R U . . .
C5 C 0.6289(2) 0.5405(3) 0.50144(13) 0.0517(7) Uani 1 1 d . . . . .
C6 C 0.6574(3) 0.6095(3) 0.54435(12) 0.0520(7) Uani 1 1 d . . . . .
H6 H 0.6128 0.5794 0.5747 0.062 Uiso 1 1 calc R U . . .
C7 C 0.7527(3) 0.7244(2) 0.54291(10) 0.0462(6) Uani 1 1 d . . . . .
H7 H 0.7739 0.7726 0.5724 0.055 Uiso 1 1 calc R U . . .
C8 C 0.4578(4) 0.3825(4) 0.5389(2) 0.0871(14) Uani 1 1 d . . . . .
H8A H 0.3994 0.3000 0.5324 0.131 Uiso 1 1 calc R U . . .
H8B H 0.4182 0.4285 0.5422 0.131 Uiso 1 1 calc R U . . .
H8C H 0.5001 0.3882 0.5705 0.131 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
O1 C1 1.199(3) . ?
O2 C5 1.380(3) . ?
O2 C8 1.399(5) . ?
N1 C1 1.390(3) . ?
N1 C1 1.396(3) 3_675 ?
N1 C2 1.457(3) . ?
C1 N1 1.397(3) 2_765 ?
C2 C7 1.358(4) . ?
C2 C3 1.393(4) . ?
C3 C4 1.382(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.360(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.376(4) . ?
C6 C7 1.400(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 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
C5 O2 C8 117.9(3) . . ?
C1 N1 C1 125.3(2) . 3_675 ?
C1 N1 C2 117.88(19) . . ?
C1 N1 C2 116.81(18) 3_675 . ?
O1 C1 N1 122.7(2) . . ?
O1 C1 N1 122.7(2) . 2_765 ?
N1 C1 N1 114.6(2) . 2_765 ?
C7 C2 C3 120.8(2) . . ?
C7 C2 N1 119.8(2) . . ?
C3 C2 N1 119.4(2) . . ?
C4 C3 C2 119.3(3) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 121.1(3) . . ?
C4 C5 O2 114.4(3) . . ?
C6 C5 O2 124.6(3) . . ?
C5 C6 C7 119.4(3) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C2 C7 C6 119.5(3) . . ?
C2 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_refine_diff_density_max         0.175
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.034


####################################################################### 
# 
# 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_4MeOC6H4NCO_dimer_orthorhombic
_database_code_depnum_ccdc_archive 'CCDC 1896216'
loop_
_audit_author_name
_audit_author_address
'Benjamin Ward'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2019-02-08 deposited with the CCDC.	2019-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 N2 O4'
_chemical_formula_weight         298.29

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.3989(3)
_cell_length_b                   5.9654(4)
_cell_length_c                   31.5160(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1391.03(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3870
_cell_measurement_theta_min      3.7530
_cell_measurement_theta_max      29.2180

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.524
_exptl_crystal_size_mid          0.267
_exptl_crystal_size_min          0.072
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.391
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45b (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5082
_diffrn_reflns_number            11260
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         3.778
_diffrn_reflns_theta_max         29.668
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1770
_reflns_number_gt                1357
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0460P)²+0.7289P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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_number_reflns         1770
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1347
_refine_ls_wR_factor_gt          0.1226
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_restrained_S_all      1.148
_refine_ls_shift/su_max          0.001
_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
O1 O 0.64212(18) 0.8063(2) 0.51764(4) 0.0388(4) Uani 1 1 d . . . . .
O2 O 0.51717(19) 0.1813(2) 0.69825(4) 0.0406(4) Uani 1 1 d . . . . .
N1 N 0.48103(18) 0.4643(3) 0.53080(4) 0.0279(3) Uani 1 1 d . . . . .
C1 C 0.5649(2) 0.6393(3) 0.50815(5) 0.0286(4) Uani 1 1 d . . . . .
C2 C 0.4934(2) 0.3860(3) 0.57292(5) 0.0255(4) Uani 1 1 d . . . . .
C3 C 0.5828(2) 0.5135(3) 0.60341(5) 0.0305(4) Uani 1 1 d . . . . .
H3 H 0.6396 0.6506 0.5958 0.037 Uiso 1 1 calc R U . . .
C4 C 0.5877(2) 0.4376(3) 0.64484(5) 0.0314(4) Uani 1 1 d . . . . .
H4 H 0.6494 0.5229 0.6658 0.038 Uiso 1 1 calc R U . . .
C5 C 0.5039(2) 0.2390(3) 0.65624(5) 0.0289(4) Uani 1 1 d . . . . .
C6 C 0.4163(2) 0.1114(3) 0.62566(6) 0.0319(4) Uani 1 1 d . . . . .
H6 H 0.3598 -0.0260 0.6332 0.038 Uiso 1 1 calc R U . . .
C7 C 0.4122(2) 0.1870(3) 0.58400(5) 0.0308(4) Uani 1 1 d . . . . .
H7 H 0.3526 0.1004 0.5629 0.037 Uiso 1 1 calc R U . . .
C8 C 0.4252(3) -0.0153(4) 0.71174(7) 0.0533(6) Uani 1 1 d . . . . .
H8A H 0.2959 -0.0003 0.7056 0.080 Uiso 1 1 calc R U . . .
H8B H 0.4425 -0.0355 0.7423 0.080 Uiso 1 1 calc R U . . .
H8C H 0.4737 -0.1455 0.6966 0.080 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
O1 C1 1.186(2) . ?
O2 C5 1.372(2) . ?
O2 C8 1.420(3) . ?
N1 C1 1.409(2) . ?
N1 C2 1.410(2) . ?
N1 C1 1.416(2) 5_666 ?
C1 N1 1.416(2) 5_666 ?
C1 C1 1.988(4) 5_666 ?
C2 C7 1.375(2) . ?
C2 C3 1.392(2) . ?
C3 C4 1.382(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(2) . ?
C6 C7 1.389(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 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
C5 O2 C8 117.50(16) . . ?
C1 N1 C2 133.93(15) . . ?
C1 N1 C1 89.44(13) . 5_666 ?
C2 N1 C1 133.40(15) . 5_666 ?
O1 C1 N1 134.96(16) . . ?
O1 C1 N1 134.47(17) . 5_666 ?
N1 C1 N1 90.56(13) . 5_666 ?
O1 C1 C1 179.6(2) . 5_666 ?
N1 C1 C1 45.42(9) . 5_666 ?
N1 C1 C1 45.14(9) 5_666 5_666 ?
C7 C2 C3 120.25(16) . . ?
C7 C2 N1 119.76(15) . . ?
C3 C2 N1 119.95(16) . . ?
C4 C3 C2 119.04(17) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 120.89(16) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
O2 C5 C4 115.68(16) . . ?
O2 C5 C6 124.45(17) . . ?
C4 C5 C6 119.87(16) . . ?
C5 C6 C7 119.24(17) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C2 C7 C6 120.70(16) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_TolNCO_trimer
_database_code_depnum_ccdc_archive 'CCDC 1896210'
loop_
_audit_author_name
_audit_author_address
'Benjamin Ward'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2019-02-08 deposited with the CCDC.	2019-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H21 N3 O3'
_chemical_formula_weight         399.44

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'

_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c :H'
_space_group_name_Hall           'R 3 -2"c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   12.6283(3)
_cell_length_b                   12.6283(3)
_cell_length_c                   26.6110(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3675.2(2)
_cell_formula_units_Z            6
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4435
_cell_measurement_theta_min      4.8210
_cell_measurement_theta_max      29.2960

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.083
_exptl_crystal_F_000             1260
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.112
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.458
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45b (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5082
_diffrn_reflns_number            6299
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         3.585
_diffrn_reflns_theta_max         29.587
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2022
_reflns_number_gt                1936
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.940
_reflns_Friedel_fraction_max     0.855
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
The structure contained highly disordered solvent, probably THF with the
oxygen atom lying on a spcial position and the remaining carbons disordered
around the 3-fold axis. After exhaustive attempts to model the disorder
were unsuccessful, the solvent was instead modelled using SQUEEZE.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0478P)²+2.3848P] 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 896 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2022
_refine_ls_number_parameters     92
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0971
_refine_ls_wR_factor_gt          0.0957
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.043
_refine_ls_shift/su_mean         0.004

# SQUEEZE RESULTS (Version = 241018)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.141 137 34 ' '
2 0.000 0.000 0.366 10 0 ' '
3 0.000 0.000 0.641 137 34 ' '
4 0.000 0.000 0.866 10 0 ' '
5 0.333 0.667 0.308 137 34 ' '
6 0.333 0.667 0.808 137 35 ' '
7 0.333 0.667 0.033 12 1 ' '
8 0.333 0.667 0.533 12 1 ' '
9 0.667 0.333 0.474 142 35 ' '
10 0.667 0.333 0.974 142 35 ' '
11 0.667 0.333 0.199 12 1 ' '
12 0.667 0.333 0.699 12 1 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?

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 0.96820(15) 0.77773(14) 0.47171(6) 0.0371(4) Uani 1 1 d . . . . .
N1 N 0.88512(15) 0.90114(15) 0.47233(7) 0.0293(4) Uani 1 1 d . . . . .
C1 C 0.98299(17) 0.87995(18) 0.47239(8) 0.0286(4) Uani 1 1 d . . . . .
C2 C 0.76352(18) 0.79741(18) 0.46812(8) 0.0289(4) Uani 1 1 d . . . . .
C3 C 0.72499(19) 0.74109(19) 0.42190(7) 0.0312(4) Uani 1 1 d . . . . .
H3 H 0.7791 0.7691 0.3940 0.037 Uiso 1 1 calc R U . . .
C4 C 0.6073(2) 0.6437(2) 0.41646(8) 0.0349(4) Uani 1 1 d . . . . .
H4 H 0.5806 0.6058 0.3846 0.042 Uiso 1 1 calc R U . . .
C5 C 0.5273(2) 0.60078(19) 0.45714(8) 0.0351(4) Uani 1 1 d . . . . .
C6 C 0.5687(2) 0.6576(2) 0.50339(8) 0.0376(5) Uani 1 1 d . . . . .
H6 H 0.5155 0.6288 0.5316 0.045 Uiso 1 1 calc R U . . .
C7 C 0.6870(2) 0.7561(2) 0.50921(8) 0.0343(4) Uani 1 1 d . . . . .
H7 H 0.7144 0.7942 0.5410 0.041 Uiso 1 1 calc R U . . .
C8 C 0.3988(2) 0.4966(3) 0.45056(11) 0.0513(6) Uani 1 1 d . . . . .
H8A H 0.3851 0.4717 0.4152 0.077 Uiso 1 1 calc R U . . .
H8B H 0.3409 0.5229 0.4608 0.077 Uiso 1 1 calc R U . . .
H8C H 0.3867 0.4274 0.4714 0.077 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
O1 C1 1.208(2) . ?
N1 C1 1.389(3) . ?
N1 C1 1.395(3) 3_675 ?
N1 C2 1.441(3) . ?
C1 N1 1.395(3) 2_765 ?
C2 C7 1.378(3) . ?
C2 C3 1.382(3) . ?
C3 C4 1.384(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(3) . ?
C5 C8 1.503(3) . ?
C6 C7 1.394(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C1 124.3(2) . 3_675 ?
C1 N1 C2 118.13(17) . . ?
C1 N1 C2 117.42(17) 3_675 . ?
O1 C1 N1 121.91(18) . . ?
O1 C1 N1 122.36(19) . 2_765 ?
N1 C1 N1 115.7(2) . 2_765 ?
C7 C2 C3 120.78(19) . . ?
C7 C2 N1 120.64(18) . . ?
C3 C2 N1 118.57(17) . . ?
C2 C3 C4 119.73(18) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.83(19) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 118.4(2) . . ?
C6 C5 C8 121.2(2) . . ?
C4 C5 C8 120.4(2) . . ?
C5 C6 C7 121.2(2) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C2 C7 C6 119.0(2) . . ?
C2 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_refine_diff_density_max         0.161
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.033


####################################################################### 
# 
# 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_TolNCO_dimer
_database_code_depnum_ccdc_archive 'CCDC 1896214'
loop_
_audit_author_name
_audit_author_address
'Benjamin Ward'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2019-02-08 deposited with the CCDC.	2019-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 N2 O2'
_chemical_formula_weight         266.29

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

_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, 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                   12.3706(9)
_cell_length_b                   11.2198(7)
_cell_length_c                   4.8807(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.853(6)
_cell_angle_gamma                90
_cell_volume                     657.72(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3660
_cell_measurement_theta_min      4.5690
_cell_measurement_theta_max      30.4060

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.78294
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.9g (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  
;
Rigaku FRE+ equipped with HF Varimax confocal mirrors and an 
AFC12 goniometer and HG Saturn 724+ detector
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            7323
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         4.301
_diffrn_reflns_theta_max         27.474
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             798
_reflns_number_gt                744
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.39.9g (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.9g (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.9g (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1073P)²+0.1272P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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_number_reflns         798
_refine_ls_number_parameters     54
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1553
_refine_ls_wR_factor_gt          0.1501
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_restrained_S_all      1.141
_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
O1 O 0.5000 0.30535(9) 0.0000 0.0267(4) Uani 1 2 d S T P . .
N1 N 0.55504(11) 0.5000 0.1871(3) 0.0224(4) Uani 1 2 d S T P . .
C1 C 0.5000 0.41118(13) 0.0000 0.0203(4) Uani 1 2 d S T P . .
C2 C 0.63926(11) 0.5000 0.4377(3) 0.0199(4) Uani 1 2 d S T P . .
C3 C 0.68126(9) 0.60742(10) 0.5609(2) 0.0248(4) Uani 1 1 d . . . . .
H3 H 0.6528 0.6794 0.4802 0.030 Uiso 1 1 calc R U . . .
C4 C 0.76607(9) 0.60603(11) 0.8053(2) 0.0267(4) Uani 1 1 d . . . . .
H4 H 0.7942 0.6780 0.8866 0.032 Uiso 1 1 calc R U . . .
C5 C 0.81014(12) 0.5000 0.9322(3) 0.0229(4) Uani 1 2 d S T P . .
C6 C 0.90110(13) 0.5000 1.1998(3) 0.0295(5) Uani 1 2 d S T P . .
H6A H 0.9554 0.4405 1.1871 0.044 Uiso 0.5 1 calc R U P . .
H6B H 0.8698 0.4826 1.3573 0.044 Uiso 0.5 1 calc R U P . .
H6C H 0.9361 0.5769 1.2255 0.044 Uiso 0.5 1 calc R U 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 C1 1.1875(19) . ?
N1 C2 1.4040(19) . ?
N1 C1 1.4118(14) 5_665 ?
N1 C1 1.4118(14) . ?
C1 N1 1.4118(14) 5_665 ?
C1 C1 1.993(3) 5_665 ?
C2 C3 1.3907(13) . ?
C2 C3 1.3908(13) 6_565 ?
C3 C4 1.3874(16) . ?
C3 H3 0.9300 . ?
C4 C5 1.3907(15) . ?
C4 H4 0.9300 . ?
C5 C4 1.3907(15) 6_565 ?
C5 C6 1.5061(18) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 134.91(6) . 5_665 ?
C2 N1 C1 134.91(6) . . ?
C1 N1 C1 89.79(12) 5_665 . ?
O1 C1 N1 134.90(6) . 5_665 ?
O1 C1 N1 134.90(6) . . ?
N1 C1 N1 90.20(12) 5_665 . ?
O1 C1 C1 180.0 . 5_665 ?
N1 C1 C1 45.10(6) 5_665 5_665 ?
N1 C1 C1 45.10(6) . 5_665 ?
C3 C2 C3 120.13(15) . 6_565 ?
C3 C2 N1 119.93(8) . . ?
C3 C2 N1 119.93(8) 6_565 . ?
C4 C3 C2 119.29(11) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 121.84(11) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C4 C5 C4 117.61(15) . 6_565 ?
C4 C5 C6 121.19(8) . . ?
C4 C5 C6 121.19(8) 6_565 . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

_refine_diff_density_max         0.582
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_4MeOC6H4NCO_dimer_monoclinic
_database_code_depnum_ccdc_archive 'CCDC 1896215'
loop_
_audit_author_name
_audit_author_address
'Benjamin Ward'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2019-02-08 deposited with the CCDC.	2019-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H14 N2 O4'
_chemical_formula_weight         298.29

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.9239(11)
_cell_length_b                   5.4001(3)
_cell_length_c                   8.0430(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.750(7)
_cell_angle_gamma                90
_cell_volume                     681.63(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1939
_cell_measurement_theta_min      3.9850
_cell_measurement_theta_max      28.6240

_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.366
_exptl_crystal_size_mid          0.289
_exptl_crystal_size_min          0.186
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.605
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45b (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5082
_diffrn_reflns_number            5462
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.895
_diffrn_reflns_theta_max         29.555
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1680
_reflns_number_gt                1307
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0737P)²+0.1739P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.058(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1680
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1427
_refine_ls_wR_factor_gt          0.1232
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
O1 O 0.48191(7) 0.1693(2) 0.64505(14) 0.0348(3) Uani 1 1 d . . . . .
O2 O 0.89939(7) 0.5273(2) 0.85575(15) 0.0355(3) Uani 1 1 d . . . . .
N1 N 0.56361(8) 0.4787(2) 0.52902(15) 0.0261(3) Uani 1 1 d . . . . .
C1 C 0.49203(9) 0.3495(3) 0.56650(18) 0.0258(4) Uani 1 1 d . . . . .
C2 C 0.64907(10) 0.4930(3) 0.60916(18) 0.0245(4) Uani 1 1 d . . . . .
C3 C 0.68247(10) 0.3136(3) 0.7259(2) 0.0288(4) Uani 1 1 d . . . . .
H3 H 0.6478 0.1803 0.7512 0.035 Uiso 1 1 calc R U . . .
C4 C 0.76644(10) 0.3303(3) 0.8050(2) 0.0303(4) Uani 1 1 d . . . . .
H4 H 0.7893 0.2085 0.8853 0.036 Uiso 1 1 calc R U . . .
C5 C 0.81760(10) 0.5244(3) 0.76773(19) 0.0275(4) Uani 1 1 d . . . . .
C6 C 0.78440(10) 0.7004(3) 0.6492(2) 0.0295(4) Uani 1 1 d . . . . .
H6 H 0.8194 0.8319 0.6222 0.035 Uiso 1 1 calc R U . . .
C7 C 0.70007(10) 0.6844(3) 0.5699(2) 0.0287(4) Uani 1 1 d . . . . .
H7 H 0.6774 0.8051 0.4887 0.034 Uiso 1 1 calc R U . . .
C8 C 0.95026(11) 0.7362(3) 0.8302(2) 0.0408(5) Uani 1 1 d . . . . .
H8A H 0.9573 0.7433 0.7116 0.061 Uiso 1 1 calc R U . . .
H8B H 1.0063 0.7213 0.9019 0.061 Uiso 1 1 calc R U . . .
H8C H 0.9222 0.8877 0.8595 0.061 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
O1 C1 1.1858(18) . ?
O2 C5 1.3731(18) . ?
O2 C8 1.424(2) . ?
N1 C2 1.4057(18) . ?
N1 C1 1.4119(18) . ?
N1 C1 1.4164(19) 3_666 ?
C1 N1 1.4164(19) 3_666 ?
C1 C1 1.986(3) 3_666 ?
C2 C7 1.384(2) . ?
C2 C3 1.390(2) . ?
C3 C4 1.383(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(2) . ?
C6 C7 1.388(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 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
C5 O2 C8 116.60(12) . . ?
C2 N1 C1 133.08(12) . . ?
C2 N1 C1 132.92(12) . 3_666 ?
C1 N1 C1 89.20(11) . 3_666 ?
O1 C1 N1 134.97(14) . . ?
O1 C1 N1 134.23(14) . 3_666 ?
N1 C1 N1 90.79(11) . 3_666 ?
O1 C1 C1 179.46(17) . 3_666 ?
N1 C1 C1 45.49(8) . 3_666 ?
N1 C1 C1 45.30(8) 3_666 3_666 ?
C7 C2 C3 120.15(14) . . ?
C7 C2 N1 119.76(13) . . ?
C3 C2 N1 120.09(13) . . ?
C4 C3 C2 119.65(14) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.40(14) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
O2 C5 C6 124.38(14) . . ?
O2 C5 C4 115.89(13) . . ?
C6 C5 C4 119.72(14) . . ?
C5 C6 C7 120.00(14) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C2 C7 C6 120.06(14) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_refine_diff_density_max         0.243
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_PhNCO_trimer
_database_code_depnum_ccdc_archive 'CCDC 1896209'
loop_
_audit_author_name
_audit_author_address
'Benjamin Ward'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2019-02-08 deposited with the CCDC.	2019-05-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H15 N3 O3'
_chemical_formula_weight         357.36

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

_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, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   23.3812(16)
_cell_length_b                   37.1191(18)
_cell_length_c                   7.7220(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6701.8(7)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4829
_cell_measurement_theta_min      3.8840
_cell_measurement_theta_max      28.7730

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_F_000             2976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.422
_exptl_crystal_size_mid          0.306
_exptl_crystal_size_min          0.118
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_T_min  0.996
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41g (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.5082
_diffrn_reflns_number            12736
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.485
_diffrn_reflns_theta_max         29.685
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.811
_diffrn_reflns_point_group_measured_fraction_full 0.924
_reflns_number_total             3863
_reflns_number_gt                3391
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.624
_reflns_Friedel_fraction_max     0.670
_reflns_Friedel_fraction_full    0.838

_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       'CrysAlisPro 1.171.38.41g (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41g (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41g (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0385P)²+10.8889P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 1179 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(6)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3863
_refine_ls_number_parameters     244
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1046
_refine_ls_wR_factor_gt          0.0972
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_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
O1 O 0.73357(9) 0.50503(5) 0.9000(3) 0.0310(5) Uani 1 1 d . . . . .
O2 O 0.59960(9) 0.46732(5) 0.5133(3) 0.0322(5) Uani 1 1 d . . . . .
O3 O 0.67073(9) 0.58092(5) 0.4758(3) 0.0301(5) Uani 1 1 d . . . . .
N1 N 0.66752(9) 0.48518(5) 0.7063(3) 0.0229(5) Uani 1 1 d . . . . .
N2 N 0.63470(9) 0.52422(6) 0.4903(3) 0.0233(5) Uani 1 1 d . . . . .
N3 N 0.70146(9) 0.54468(5) 0.6957(3) 0.0231(5) Uani 1 1 d . . . . .
C1 C 0.70376(11) 0.51107(7) 0.7763(4) 0.0234(6) Uani 1 1 d . . . . .
C2 C 0.63143(11) 0.49027(7) 0.5658(4) 0.0245(6) Uani 1 1 d . . . . .
C3 C 0.66979(11) 0.55203(6) 0.5477(4) 0.0230(6) Uani 1 1 d . . . . .
C4 C 0.66540(11) 0.45006(6) 0.7882(4) 0.0221(5) Uani 1 1 d . . . . .
C5 C 0.61873(12) 0.44161(7) 0.8909(4) 0.0291(6) Uani 1 1 d . . . . .
H5 H 0.5898 0.4590 0.9125 0.035 Uiso 1 1 calc R U . . .
C6 C 0.61475(13) 0.40743(8) 0.9617(4) 0.0323(7) Uani 1 1 d . . . . .
H6 H 0.5826 0.4011 1.0306 0.039 Uiso 1 1 calc R U . . .
C7 C 0.65779(13) 0.38237(7) 0.9320(4) 0.0307(6) Uani 1 1 d . . . . .
H7 H 0.6549 0.3588 0.9792 0.037 Uiso 1 1 calc R U . . .
C8 C 0.70458(13) 0.39173(7) 0.8344(4) 0.0317(7) Uani 1 1 d . . . . .
H8 H 0.7346 0.3748 0.8181 0.038 Uiso 1 1 calc R U . . .
C9 C 0.70841(13) 0.42561(7) 0.7593(4) 0.0289(6) Uani 1 1 d . . . . .
H9 H 0.7403 0.4318 0.6890 0.035 Uiso 1 1 calc R U . . .
C10 C 0.59908(12) 0.53109(6) 0.3406(4) 0.0242(6) Uani 1 1 d . . . . .
C11 C 0.54191(12) 0.53868(7) 0.3638(4) 0.0272(6) Uani 1 1 d . . . . .
H11 H 0.5258 0.5389 0.4768 0.033 Uiso 1 1 calc R U . . .
C12 C 0.50811(12) 0.54595(8) 0.2208(5) 0.0306(7) Uani 1 1 d . . . . .
H12 H 0.4686 0.5511 0.2353 0.037 Uiso 1 1 calc R U . . .
C13 C 0.53186(13) 0.54565(7) 0.0573(4) 0.0303(7) Uani 1 1 d . . . . .
H13 H 0.5087 0.5508 -0.0408 0.036 Uiso 1 1 calc R U . . .
C14 C 0.58916(13) 0.53794(7) 0.0361(4) 0.0304(6) Uani 1 1 d . . . . .
H14 H 0.6052 0.5378 -0.0769 0.037 Uiso 1 1 calc R U . . .
C15 C 0.62341(12) 0.53048(7) 0.1772(4) 0.0281(6) Uani 1 1 d . . . . .
H15 H 0.6628 0.5250 0.1625 0.034 Uiso 1 1 calc R U . . .
C16 C 0.73427(11) 0.57401(7) 0.7696(4) 0.0239(6) Uani 1 1 d . . . . .
C17 C 0.70555(12) 0.60443(7) 0.8257(4) 0.0296(6) Uani 1 1 d . . . . .
H17 H 0.6650 0.6054 0.8218 0.036 Uiso 1 1 calc R U . . .
C18 C 0.73672(13) 0.63352(8) 0.8876(5) 0.0323(7) Uani 1 1 d . . . . .
H18 H 0.7176 0.6548 0.9232 0.039 Uiso 1 1 calc R U . . .
C19 C 0.79525(13) 0.63146(8) 0.8974(4) 0.0314(7) Uani 1 1 d . . . . .
H19 H 0.8165 0.6515 0.9385 0.038 Uiso 1 1 calc R U . . .
C20 C 0.82356(12) 0.60029(8) 0.8478(4) 0.0312(6) Uani 1 1 d . . . . .
H20 H 0.8639 0.5986 0.8598 0.037 Uiso 1 1 calc R U . . .
C21 C 0.79294(12) 0.57159(7) 0.7808(4) 0.0273(6) Uani 1 1 d . . . . .
H21 H 0.8122 0.5505 0.7429 0.033 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
O1 C1 1.204(3) . ?
O2 C2 1.201(3) . ?
O3 C3 1.208(3) . ?
N1 C2 1.388(4) . ?
N1 C1 1.391(3) . ?
N1 C4 1.450(3) . ?
N2 C2 1.390(3) . ?
N2 C3 1.391(3) . ?
N2 C10 1.447(4) . ?
N3 C3 1.389(4) . ?
N3 C1 1.395(3) . ?
N3 C16 1.449(3) . ?
C4 C9 1.373(4) . ?
C4 C5 1.385(4) . ?
C5 C6 1.385(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.389(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.373(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.388(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.378(4) . ?
C10 C15 1.384(4) . ?
C11 C12 1.384(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.379(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C21 1.377(4) . ?
C16 C17 1.383(4) . ?
C17 C18 1.388(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.373(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.387(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.384(4) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 125.5(2) . . ?
C2 N1 C4 116.3(2) . . ?
C1 N1 C4 118.2(2) . . ?
C2 N2 C3 124.9(2) . . ?
C2 N2 C10 117.6(2) . . ?
C3 N2 C10 117.6(2) . . ?
C3 N3 C1 124.3(2) . . ?
C3 N3 C16 117.3(2) . . ?
C1 N3 C16 118.4(2) . . ?
O1 C1 N1 122.2(2) . . ?
O1 C1 N3 122.9(2) . . ?
N1 C1 N3 114.9(2) . . ?
O2 C2 N1 122.9(2) . . ?
O2 C2 N2 122.4(3) . . ?
N1 C2 N2 114.7(2) . . ?
O3 C3 N3 122.9(2) . . ?
O3 C3 N2 121.6(3) . . ?
N3 C3 N2 115.5(2) . . ?
C9 C4 C5 121.4(2) . . ?
C9 C4 N1 119.9(2) . . ?
C5 C4 N1 118.7(2) . . ?
C6 C5 C4 119.1(3) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C7 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 119.9(3) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 120.7(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C4 C9 C8 118.9(3) . . ?
C4 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C11 C10 C15 121.4(3) . . ?
C11 C10 N2 119.4(3) . . ?
C15 C10 N2 119.2(2) . . ?
C10 C11 C12 119.3(3) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.7(3) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C14 C15 C10 118.6(3) . . ?
C14 C15 H15 120.7 . . ?
C10 C15 H15 120.7 . . ?
C21 C16 C17 121.1(2) . . ?
C21 C16 N3 120.2(2) . . ?
C17 C16 N3 118.7(2) . . ?
C16 C17 C18 119.2(3) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C19 C18 C17 119.9(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C20 120.5(3) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C21 C20 C19 119.9(3) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C16 C21 C20 119.2(3) . . ?
C16 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.054

