# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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 
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data_cu_mplu62_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1587592'
_audit_update_record             
;
2017-11-25 deposited with the CCDC.
2018-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
N,N',N''-(nitrilotris(ethane-2,1-diyl))tris(2-fluorobenzamide)
_chemical_name_common            2F-baTren
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H27 F3 N4 O3'
_chemical_formula_weight         512.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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                   7.3234(2)
_cell_length_b                   33.2434(9)
_cell_length_c                   10.4467(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.8150(10)
_cell_angle_gamma                90
_cell_volume                     2458.75(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6176
_cell_measurement_theta_min      4.58
_cell_measurement_theta_max      66.60

_exptl_crystal_description       cut-prizm
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.902
_shelx_estimated_absorpt_T_min   0.907
_shelx_estimated_absorpt_T_max   0.915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6930
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14173
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.658
_diffrn_reflns_theta_max         66.590
_diffrn_reflns_theta_full        66.590
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4340
_reflns_number_gt                3692
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0485P)²+0.5400P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4340
_refine_ls_number_parameters     448
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0986
_refine_ls_wR_factor_gt          0.0936
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.033
_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 0.28063(18) 0.46561(3) 0.63660(11) 0.0490(3) Uani 1 1 d . . . . .
O2 O 0.58023(15) 0.38920(3) 0.17934(10) 0.0396(3) Uani 1 1 d . . . . .
O3 O -0.01260(17) 0.30981(4) 0.13082(14) 0.0580(4) Uani 1 1 d . . . . .
F1 F 0.34009(14) 0.35618(3) 0.45328(9) 0.0477(2) Uani 1 1 d . . . . .
F2 F 0.69337(15) 0.44665(3) 0.54136(9) 0.0471(2) Uani 1 1 d . . . . .
N1 N 0.19666(16) 0.44739(4) 0.16371(11) 0.0323(3) Uani 1 1 d . . . . .
N2 N 0.20927(18) 0.43269(4) 0.44339(12) 0.0354(3) Uani 1 1 d . . . . .
N3 N 0.61054(17) 0.45095(4) 0.27068(12) 0.0325(3) Uani 1 1 d . . . . .
N4 N 0.1937(2) 0.35838(4) 0.11591(13) 0.0396(3) Uani 1 1 d . . . . .
C1 C 0.0461(2) 0.45905(5) 0.22561(15) 0.0380(4) Uani 1 1 d . . . . .
C2 C 0.1183(2) 0.46770(5) 0.37171(15) 0.0396(4) Uani 1 1 d . . . . .
C3 C 0.2869(2) 0.43454(5) 0.57386(14) 0.0346(3) Uani 1 1 d . . . . .
C4 C 0.3790(2) 0.39745(4) 0.64404(14) 0.0337(3) Uani 1 1 d . . . . .
C5 C 0.4008(2) 0.36062(5) 0.58712(15) 0.0372(3) Uani 1 1 d . . . . .
C6 C 0.4823(2) 0.32768(5) 0.65866(18) 0.0453(4) Uani 1 1 d . . . . .
C7 C 0.5483(3) 0.33097(5) 0.79483(18) 0.0480(4) Uani 1 1 d . . . . .
C8 C 0.5316(2) 0.36721(5) 0.85644(17) 0.0458(4) Uani 1 1 d . . . . .
C9 C 0.4482(2) 0.39973(5) 0.78180(15) 0.0393(4) Uani 1 1 d . . . . .
C10 C 0.3124(2) 0.48218(5) 0.14904(16) 0.0375(3) Uani 1 1 d . . . . .
C11 C 0.5128(2) 0.47073(5) 0.14852(15) 0.0362(3) Uani 1 1 d . . . . .
C12 C 0.63567(19) 0.41107(4) 0.27726(14) 0.0319(3) Uani 1 1 d . . . . .
C13 C 0.74369(19) 0.39283(4) 0.40576(14) 0.0320(3) Uani 1 1 d . . . . .
C14 C 0.7722(2) 0.41012(4) 0.52986(15) 0.0347(3) Uani 1 1 d . . . . .
C15 C 0.8732(2) 0.39213(5) 0.64456(16) 0.0429(4) Uani 1 1 d . . . . .
C16 C 0.9483(2) 0.35443(6) 0.63673(18) 0.0476(4) Uani 1 1 d . . . . .
C17 C 0.9226(2) 0.33573(6) 0.51564(18) 0.0481(4) Uani 1 1 d . . . . .
C18 C 0.8217(2) 0.35455(5) 0.40152(17) 0.0408(4) Uani 1 1 d . . . . .
C19 C 0.1198(2) 0.42743(5) 0.03672(14) 0.0389(4) Uani 1 1 d . . . . .
C20 C 0.0448(2) 0.38554(5) 0.04841(16) 0.0420(4) Uani 1 1 d . . . . .
C21 C 0.1520(2) 0.32140(5) 0.14991(15) 0.0403(4) Uani 1 1 d . . . . .
C22 C 0.3163(2) 0.29462(4) 0.20786(16) 0.0393(4) Uani 1 1 d . . . . .
C23 C 0.3177(3) 0.26978(5) 0.31403(17) 0.0487(4) Uani 0.864(3) 1 d D . P A 1
C27 C 0.4733(2) 0.29221(5) 0.15584(17) 0.0454(4) Uani 0.864(3) 1 d . . P A 1
H27 H 0.4772 0.3086 0.0821 0.054 Uiso 0.864(3) 1 calc R U P A 1
F3 F 0.1671(2) 0.27086(4) 0.36731(13) 0.0680(5) Uani 0.864(3) 1 d D . P A 1
C23A C 0.3177(3) 0.26978(5) 0.31403(17) 0.0487(4) Uani 0.136(3) 1 d . . P A 2
H23 H 0.2111 0.2700 0.3501 0.058 Uiso 0.136(3) 1 calc R U P A 2
C27A C 0.4733(2) 0.29221(5) 0.15584(17) 0.0454(4) Uani 0.136(3) 1 d D . P A 2
F3A F 0.4887(10) 0.3073(2) 0.0509(6) 0.052(2) Uani 0.136(3) 1 d D . P A 2
C24 C 0.4654(3) 0.24474(5) 0.36989(19) 0.0618(5) Uani 1 1 d . . . . .
C25 C 0.6177(3) 0.24312(5) 0.3150(2) 0.0602(5) Uani 1 1 d . . . . .
C26 C 0.6232(3) 0.26690(5) 0.2076(2) 0.0534(5) Uani 1 1 d . . . . .
H1A H -0.023(2) 0.4835(5) 0.1820(17) 0.042(4) Uiso 1 1 d . . . . .
H1B H -0.042(2) 0.4365(5) 0.2127(16) 0.039(4) Uiso 1 1 d . . . . .
H2A H 0.206(2) 0.4904(5) 0.3870(16) 0.040(4) Uiso 1 1 d . . . . .
H2B H 0.011(3) 0.4761(5) 0.4079(18) 0.052(5) Uiso 1 1 d . . . . .
H2N H 0.226(2) 0.4112(6) 0.4022(17) 0.042(5) Uiso 1 1 d . . . . .
H3N H 0.647(3) 0.4662(5) 0.3369(19) 0.046(5) Uiso 1 1 d . . . . .
H4N H 0.305(3) 0.3668(5) 0.1366(18) 0.043(5) Uiso 1 1 d . . . . .
H6 H 0.490(3) 0.3035(6) 0.6113(18) 0.052(5) Uiso 1 1 d . . . . .
H7 H 0.606(3) 0.3077(6) 0.8462(19) 0.058(5) Uiso 1 1 d . . . . .
H8 H 0.574(3) 0.3700(5) 0.9520(19) 0.050(5) Uiso 1 1 d . . . . .
H9 H 0.438(2) 0.4263(5) 0.8275(15) 0.032(4) Uiso 1 1 d . . . . .
H10A H 0.252(2) 0.4982(5) 0.0669(17) 0.045(5) Uiso 1 1 d . . . . .
H10B H 0.322(2) 0.5015(5) 0.2284(16) 0.035(4) Uiso 1 1 d . . . . .
H11A H 0.584(2) 0.4958(5) 0.1390(16) 0.040(4) Uiso 1 1 d . . . . .
H11B H 0.517(2) 0.4525(5) 0.0773(17) 0.035(4) Uiso 1 1 d . . . . .
H15 H 0.883(2) 0.4066(5) 0.7253(18) 0.048(5) Uiso 1 1 d . . . . .
H16 H 1.014(2) 0.3412(5) 0.7165(18) 0.047(5) Uiso 1 1 d . . . . .
H17 H 0.973(3) 0.3095(6) 0.5099(19) 0.055(5) Uiso 1 1 d . . . . .
H18 H 0.805(2) 0.3421(5) 0.3165(18) 0.043(5) Uiso 1 1 d . . . . .
H19A H 0.224(2) 0.4249(5) -0.0110(16) 0.039(4) Uiso 1 1 d . . . . .
H19B H 0.012(2) 0.4442(5) -0.0250(17) 0.045(5) Uiso 1 1 d . . . . .
H20A H -0.056(2) 0.3857(5) 0.0949(18) 0.045(5) Uiso 1 1 d . . . . .
H20B H -0.013(2) 0.3750(5) -0.0436(18) 0.045(5) Uiso 1 1 d . . . . .
H24 H 0.457(3) 0.2270(7) 0.446(2) 0.076(7) Uiso 1 1 d . . . . .
H25 H 0.724(3) 0.2265(6) 0.349(2) 0.069(6) Uiso 1 1 d . . . . .
H26 H 0.733(3) 0.2651(5) 0.1718(18) 0.047(5) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.2303(18) . ?
O2 C12 1.2360(17) . ?
O3 C21 1.2320(19) . ?
F1 C5 1.3625(17) . ?
F2 C14 1.3629(17) . ?
N1 C19 1.4613(19) . ?
N1 C1 1.4657(19) . ?
N1 C10 1.4650(19) . ?
N2 C3 1.3373(19) . ?
N2 C2 1.451(2) . ?
N2 H2N 0.857(19) . ?
N3 C12 1.3378(19) . ?
N3 C11 1.4513(19) . ?
N3 H3N 0.845(19) . ?
N4 C21 1.337(2) . ?
N4 C20 1.452(2) . ?
N4 H4N 0.838(19) . ?
C1 C2 1.510(2) . ?
C1 H1A 1.005(17) . ?
C1 H1B 0.976(17) . ?
C2 H2A 0.978(17) . ?
C2 H2B 0.992(19) . ?
C3 C4 1.503(2) . ?
C4 C5 1.388(2) . ?
C4 C9 1.400(2) . ?
C5 C6 1.373(2) . ?
C6 C7 1.385(3) . ?
C6 H6 0.954(19) . ?
C7 C8 1.386(3) . ?
C7 H7 0.97(2) . ?
C8 C9 1.380(2) . ?
C8 H8 0.971(19) . ?
C9 H9 1.017(16) . ?
C10 C11 1.517(2) . ?
C10 H10A 1.011(17) . ?
C10 H10B 1.037(16) . ?
C11 H11A 1.001(17) . ?
C11 H11B 0.968(17) . ?
C12 C13 1.501(2) . ?
C13 C14 1.384(2) . ?
C13 C18 1.400(2) . ?
C14 C15 1.374(2) . ?
C15 C16 1.380(3) . ?
C15 H15 0.957(18) . ?
C16 C17 1.378(3) . ?
C16 H16 0.956(18) . ?
C17 C18 1.382(2) . ?
C17 H17 0.95(2) . ?
C18 H18 0.959(18) . ?
C19 C20 1.513(2) . ?
C19 H19A 1.014(17) . ?
C19 H19B 1.046(18) . ?
C20 H20A 0.983(18) . ?
C20 H20B 1.008(18) . ?
C21 C22 1.495(2) . ?
C22 C23A 1.381(2) . ?
C22 C23 1.381(2) . ?
C22 C27A 1.394(2) . ?
C22 C27 1.394(2) . ?
C23 F3 1.357(2) . ?
C23 C24 1.371(3) . ?
C27 C26 1.379(3) . ?
C27 H27 0.9500 . ?
C23A C24 1.371(3) . ?
C23A H23 0.9500 . ?
C27A F3A 1.236(6) . ?
C27A C26 1.379(3) . ?
C24 C25 1.379(3) . ?
C24 H24 1.01(2) . ?
C25 C26 1.382(3) . ?
C25 H25 0.95(2) . ?
C26 H26 0.974(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 N1 C1 111.23(12) . . ?
C19 N1 C10 111.25(12) . . ?
C1 N1 C10 110.98(12) . . ?
C3 N2 C2 120.57(13) . . ?
C3 N2 H2N 118.2(12) . . ?
C2 N2 H2N 120.9(12) . . ?
C12 N3 C11 121.64(13) . . ?
C12 N3 H3N 122.9(12) . . ?
C11 N3 H3N 115.4(12) . . ?
C21 N4 C20 120.42(14) . . ?
C21 N4 H4N 120.9(12) . . ?
C20 N4 H4N 118.6(12) . . ?
N1 C1 C2 112.84(13) . . ?
N1 C1 H1A 111.4(10) . . ?
C2 C1 H1A 108.1(10) . . ?
N1 C1 H1B 106.2(10) . . ?
C2 C1 H1B 109.5(10) . . ?
H1A C1 H1B 108.7(13) . . ?
N2 C2 C1 111.41(13) . . ?
N2 C2 H2A 109.7(10) . . ?
C1 C2 H2A 110.9(10) . . ?
N2 C2 H2B 109.3(11) . . ?
C1 C2 H2B 109.4(11) . . ?
H2A C2 H2B 105.9(14) . . ?
O1 C3 N2 121.18(15) . . ?
O1 C3 C4 120.13(13) . . ?
N2 C3 C4 118.68(13) . . ?
C5 C4 C9 115.90(14) . . ?
C5 C4 C3 126.94(13) . . ?
C9 C4 C3 117.15(13) . . ?
F1 C5 C6 117.02(14) . . ?
F1 C5 C4 119.48(14) . . ?
C6 C5 C4 123.50(15) . . ?
C5 C6 C7 119.01(16) . . ?
C5 C6 H6 117.8(11) . . ?
C7 C6 H6 123.2(11) . . ?
C6 C7 C8 119.77(17) . . ?
C6 C7 H7 119.5(12) . . ?
C8 C7 H7 120.8(12) . . ?
C9 C8 C7 119.82(16) . . ?
C9 C8 H8 119.0(11) . . ?
C7 C8 H8 121.2(11) . . ?
C8 C9 C4 122.00(15) . . ?
C8 C9 H9 119.4(9) . . ?
C4 C9 H9 118.6(9) . . ?
N1 C10 C11 112.86(13) . . ?
N1 C10 H10A 111.5(10) . . ?
C11 C10 H10A 110.0(10) . . ?
N1 C10 H10B 109.3(9) . . ?
C11 C10 H10B 106.7(9) . . ?
H10A C10 H10B 106.1(13) . . ?
N3 C11 C10 111.76(12) . . ?
N3 C11 H11A 108.2(9) . . ?
C10 C11 H11A 108.5(9) . . ?
N3 C11 H11B 106.6(9) . . ?
C10 C11 H11B 112.6(9) . . ?
H11A C11 H11B 109.0(13) . . ?
O2 C12 N3 121.92(13) . . ?
O2 C12 C13 119.28(13) . . ?
N3 C12 C13 118.71(13) . . ?
C14 C13 C18 116.23(14) . . ?
C14 C13 C12 126.07(13) . . ?
C18 C13 C12 117.70(13) . . ?
F2 C14 C15 117.16(14) . . ?
F2 C14 C13 119.12(13) . . ?
C15 C14 C13 123.70(15) . . ?
C14 C15 C16 118.53(16) . . ?
C14 C15 H15 116.9(11) . . ?
C16 C15 H15 124.5(11) . . ?
C17 C16 C15 120.07(16) . . ?
C17 C16 H16 120.9(11) . . ?
C15 C16 H16 119.0(11) . . ?
C16 C17 C18 120.34(17) . . ?
C16 C17 H17 120.3(12) . . ?
C18 C17 H17 119.3(12) . . ?
C17 C18 C13 121.12(16) . . ?
C17 C18 H18 121.1(10) . . ?
C13 C18 H18 117.8(10) . . ?
N1 C19 C20 114.09(13) . . ?
N1 C19 H19A 108.7(9) . . ?
C20 C19 H19A 107.3(9) . . ?
N1 C19 H19B 111.9(10) . . ?
C20 C19 H19B 107.9(10) . . ?
H19A C19 H19B 106.6(13) . . ?
N4 C20 C19 111.61(13) . . ?
N4 C20 H20A 109.2(10) . . ?
C19 C20 H20A 111.8(10) . . ?
N4 C20 H20B 109.2(10) . . ?
C19 C20 H20B 108.3(10) . . ?
H20A C20 H20B 106.6(14) . . ?
O3 C21 N4 121.70(16) . . ?
O3 C21 C22 122.15(15) . . ?
N4 C21 C22 116.11(14) . . ?
C23A C22 C27A 116.21(16) . . ?
C23 C22 C27 116.21(16) . . ?
C23A C22 C21 121.40(15) . . ?
C23 C22 C21 121.40(15) . . ?
C27A C22 C21 122.36(15) . . ?
C27 C22 C21 122.36(15) . . ?
F3 C23 C24 118.47(17) . . ?
F3 C23 C22 118.30(17) . . ?
C24 C23 C22 123.21(17) . . ?
C26 C27 C22 122.36(17) . . ?
C26 C27 H27 118.8 . . ?
C22 C27 H27 118.8 . . ?
C24 C23A C22 123.21(17) . . ?
C24 C23A H23 118.4 . . ?
C22 C23A H23 118.4 . . ?
F3A C27A C26 110.6(4) . . ?
F3A C27A C22 126.4(4) . . ?
C26 C27A C22 122.36(17) . . ?
C23A C24 C25 118.71(19) . . ?
C23 C24 C25 118.71(19) . . ?
C23A C24 H24 119.5(13) . . ?
C23 C24 H24 119.5(13) . . ?
C25 C24 H24 121.7(13) . . ?
C24 C25 C26 120.7(2) . . ?
C24 C25 H25 122.7(13) . . ?
C26 C25 H25 116.6(13) . . ?
C27A C26 C25 118.80(19) . . ?
C27 C26 C25 118.80(19) . . ?
C27A C26 H26 122.8(11) . . ?
C27 C26 H26 122.8(11) . . ?
C25 C26 H26 118.4(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C19 N1 C1 C2 162.17(13) . . . . ?
C10 N1 C1 C2 -73.40(16) . . . . ?
C3 N2 C2 C1 178.33(13) . . . . ?
N1 C1 C2 N2 -60.37(19) . . . . ?
C2 N2 C3 O1 1.1(2) . . . . ?
C2 N2 C3 C4 179.76(13) . . . . ?
O1 C3 C4 C5 -178.47(15) . . . . ?
N2 C3 C4 C5 2.9(2) . . . . ?
O1 C3 C4 C9 2.5(2) . . . . ?
N2 C3 C4 C9 -176.10(13) . . . . ?
C9 C4 C5 F1 -178.84(13) . . . . ?
C3 C4 C5 F1 2.2(2) . . . . ?
C9 C4 C5 C6 0.9(2) . . . . ?
C3 C4 C5 C6 -178.14(15) . . . . ?
F1 C5 C6 C7 179.15(15) . . . . ?
C4 C5 C6 C7 -0.6(3) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C6 C7 C8 C9 0.4(3) . . . . ?
C7 C8 C9 C4 0.0(3) . . . . ?
C5 C4 C9 C8 -0.6(2) . . . . ?
C3 C4 C9 C8 178.54(14) . . . . ?
C19 N1 C10 C11 -82.67(15) . . . . ?
C1 N1 C10 C11 152.91(13) . . . . ?
C12 N3 C11 C10 102.75(16) . . . . ?
N1 C10 C11 N3 -60.23(18) . . . . ?
C11 N3 C12 O2 1.4(2) . . . . ?
C11 N3 C12 C13 178.02(12) . . . . ?
O2 C12 C13 C14 -161.96(14) . . . . ?
N3 C12 C13 C14 21.3(2) . . . . ?
O2 C12 C13 C18 17.2(2) . . . . ?
N3 C12 C13 C18 -159.56(13) . . . . ?
C18 C13 C14 F2 -177.35(13) . . . . ?
C12 C13 C14 F2 1.8(2) . . . . ?
C18 C13 C14 C15 1.2(2) . . . . ?
C12 C13 C14 C15 -179.72(14) . . . . ?
F2 C14 C15 C16 177.45(14) . . . . ?
C13 C14 C15 C16 -1.1(2) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C15 C16 C17 C18 0.0(3) . . . . ?
C16 C17 C18 C13 0.1(3) . . . . ?
C14 C13 C18 C17 -0.6(2) . . . . ?
C12 C13 C18 C17 -179.84(15) . . . . ?
C1 N1 C19 C20 -71.54(17) . . . . ?
C10 N1 C19 C20 164.19(13) . . . . ?
C21 N4 C20 C19 171.92(14) . . . . ?
N1 C19 C20 N4 -63.71(18) . . . . ?
C20 N4 C21 O3 -3.3(2) . . . . ?
C20 N4 C21 C22 174.68(13) . . . . ?
O3 C21 C22 C23A -43.0(2) . . . . ?
N4 C21 C22 C23A 139.07(16) . . . . ?
O3 C21 C22 C23 -43.0(2) . . . . ?
N4 C21 C22 C23 139.07(16) . . . . ?
O3 C21 C22 C27A 134.85(17) . . . . ?
N4 C21 C22 C27A -43.1(2) . . . . ?
O3 C21 C22 C27 134.85(17) . . . . ?
N4 C21 C22 C27 -43.1(2) . . . . ?
C27 C22 C23 F3 -179.50(14) . . . . ?
C21 C22 C23 F3 -1.5(2) . . . . ?
C27 C22 C23 C24 1.9(2) . . . . ?
C21 C22 C23 C24 179.90(14) . . . . ?
C23 C22 C27 C26 -0.7(2) . . . . ?
C21 C22 C27 C26 -178.65(15) . . . . ?
C27A C22 C23A C24 1.9(2) . . . . ?
C21 C22 C23A C24 179.90(14) . . . . ?
C23A C22 C27A F3A 169.1(4) . . . . ?
C21 C22 C27A F3A -8.9(5) . . . . ?
C23A C22 C27A C26 -0.7(2) . . . . ?
C21 C22 C27A C26 -178.65(15) . . . . ?
C22 C23A C24 C25 -2.3(2) . . . . ?
F3 C23 C24 C25 179.14(15) . . . . ?
C22 C23 C24 C25 -2.3(2) . . . . ?
C23A C24 C25 C26 1.4(2) . . . . ?
C23 C24 C25 C26 1.4(2) . . . . ?
F3A C27A C26 C25 -171.3(4) . . . . ?
C22 C27A C26 C25 -0.1(3) . . . . ?
C22 C27 C26 C25 -0.1(3) . . . . ?
C24 C25 C26 C27A -0.2(3) . . . . ?
C24 C25 C26 C27 -0.2(3) . . . . ?

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
C2 H2A F2 0.978(17) 2.281(18) 3.193(2) 154.7(13) 3_666
N2 H2N F1 0.857(19) 2.027(18) 2.7105(16) 136.1(15) .
N3 H3N O1 0.845(19) 2.328(18) 2.9786(17) 134.2(16) 3_666
N3 H3N F2 0.845(19) 2.174(18) 2.7400(15) 124.2(15) .
N4 H4N O2 0.838(19) 2.085(19) 2.9225(18) 177.3(18) .
C11 H11A O1 1.001(17) 2.633(16) 3.173(2) 113.9(11) 3_666
C24 H24 O3 1.01(2) 2.25(2) 3.244(2) 170.9(18) 4_666
C26 H26 O3 0.974(19) 2.502(19) 3.299(2) 139.0(14) 1_655

_refine_diff_density_max         0.152
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.038


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol/Ether'
####################################################################### 
# 
# 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_cu_mplu58_0m
_database_code_depnum_ccdc_archive 'CCDC 1587594'
_audit_update_record             
;
2017-11-25 deposited with the CCDC.
2018-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
N,N',N''-(nitrilotris(ethane-2,1-diyl))tris(4-(trifluoromethyl)benzamide)
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H27 F9 N4 O3'
_chemical_formula_weight         662.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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                   8.6772(2)
_cell_length_b                   12.4885(3)
_cell_length_c                   14.3777(3)
_cell_angle_alpha                88.8410(10)
_cell_angle_beta                 85.9900(10)
_cell_angle_gamma                69.9560(10)
_cell_volume                     1460.08(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8362
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      66.86

_exptl_crystal_description       cut-prizm
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.206
_shelx_estimated_absorpt_T_min   0.812
_shelx_estimated_absorpt_T_max   0.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6835
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18883
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.081
_diffrn_reflns_theta_max         66.853
_diffrn_reflns_theta_full        66.853
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             5112
_reflns_number_gt                4415
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0525P)²+1.0720P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5112
_refine_ls_number_parameters     562
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1267
_refine_ls_wR_factor_gt          0.1203
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 1.1573(2) 0.96295(13) 0.57583(9) 0.0401(4) Uani 1 1 d . . . . .
O2 O 0.60225(17) 1.07540(13) 0.75798(9) 0.0355(3) Uani 1 1 d . . . . .
O3 O 0.7712(2) 1.08236(13) 1.07760(9) 0.0435(4) Uani 1 1 d . . . . .
N1 N 0.89106(18) 1.18978(12) 0.75658(10) 0.0238(3) Uani 1 1 d . . . . .
N2 N 0.7788(2) 1.09846(14) 0.92195(11) 0.0284(4) Uani 1 1 d . . . . .
N3 N 0.7106(2) 1.09822(14) 0.61460(11) 0.0295(4) Uani 1 1 d . . . . .
N4 N 1.19214(19) 0.98510(13) 0.72720(11) 0.0262(3) Uani 1 1 d . . . . .
C1 C 0.7723(2) 1.26333(16) 0.82601(13) 0.0283(4) Uani 1 1 d . . . . .
C2 C 0.7868(3) 1.21292(17) 0.92346(13) 0.0301(4) Uani 1 1 d . . . . .
C3 C 0.7700(2) 1.04178(17) 1.00013(12) 0.0282(4) Uani 1 1 d . . . . .
C4 C 0.7564(2) 0.92609(17) 0.99141(12) 0.0278(4) Uani 1 1 d . . . . .
C5 C 0.6529(2) 0.89490(18) 1.05642(13) 0.0304(4) Uani 1 1 d . . . . .
C6 C 0.6383(2) 0.78869(18) 1.05283(14) 0.0336(5) Uani 1 1 d . . . . .
C7 C 0.7282(3) 0.71104(18) 0.98422(15) 0.0354(5) Uani 1 1 d . . . . .
C8 C 0.8343(3) 0.74076(19) 0.92034(15) 0.0379(5) Uani 1 1 d . . . . .
C9 C 0.8475(2) 0.84791(18) 0.92357(14) 0.0328(4) Uani 1 1 d . . . . .
C10 C 0.7069(3) 0.5981(2) 0.97705(18) 0.0483(6) Uani 1 1 d . . . . .
C11 C 0.8510(3) 1.23129(17) 0.66188(13) 0.0289(4) Uani 1 1 d . . . . .
C12 C 0.6971(3) 1.21597(17) 0.62910(14) 0.0314(4) Uani 1 1 d . . . . .
C13 C 0.6552(2) 1.03859(17) 0.67838(13) 0.0275(4) Uani 1 1 d . . . . .
C14 C 0.6537(2) 0.92388(17) 0.64988(13) 0.0285(4) Uani 1 1 d . . . . .
C15 C 0.6322(3) 0.85144(19) 0.72031(15) 0.0365(5) Uani 1 1 d . . . . .
C16 C 0.6290(3) 0.7449(2) 0.69959(16) 0.0414(5) Uani 1 1 d . . . . .
C17 C 0.6425(3) 0.71029(18) 0.60790(16) 0.0379(5) Uani 1 1 d . . . . .
C18 C 0.6595(3) 0.78294(19) 0.53673(16) 0.0403(5) Uani 1 1 d . . . . .
C19 C 0.6660(3) 0.88875(19) 0.55740(14) 0.0352(5) Uani 1 1 d . . . . .
C20 C 0.6399(3) 0.5953(2) 0.58501(19) 0.0495(6) Uani 1 1 d . . . . .
C21 C 1.0568(2) 1.18553(16) 0.77504(13) 0.0271(4) Uani 1 1 d . . . . .
C22 C 1.1954(2) 1.10024(16) 0.71672(14) 0.0281(4) Uani 1 1 d . . . . .
C23 C 1.1721(2) 0.92550(16) 0.65627(12) 0.0267(4) Uani 1 1 d . . . . .
C24 C 1.1656(2) 0.80895(16) 0.67694(13) 0.0276(4) Uani 1 1 d . . . . .
C25 C 1.0956(3) 0.76095(18) 0.61275(14) 0.0337(5) Uani 1 1 d . . . . .
C26 C 1.0905(3) 0.65218(19) 0.62570(16) 0.0392(5) Uani 1 1 d . . . . .
C27 C 1.1572(3) 0.59027(18) 0.70319(15) 0.0388(5) Uani 1 1 d . . . . .
C28 C 1.2265(3) 0.63747(18) 0.76812(16) 0.0392(5) Uani 1 1 d . . . . .
C29 C 1.2299(3) 0.74660(17) 0.75551(14) 0.0332(4) Uani 1 1 d . . . . .
C30 C 1.1523(4) 0.4731(2) 0.71913(19) 0.0539(7) Uani 1 1 d . . . . .
F1 F 0.6191(3) 0.57446(17) 1.05114(14) 0.0662(8) Uani 0.854(6) 1 d . . P . .
F2 F 0.6218(6) 0.5928(3) 0.9048(2) 0.1088(15) Uani 0.854(6) 1 d . . P . .
F3 F 0.8439(3) 0.51210(16) 0.9712(3) 0.1006(13) Uani 0.854(6) 1 d . . P . .
F4 F 0.5837(7) 0.5438(3) 0.6520(4) 0.1001(16) Uani 0.758(8) 1 d . . P . .
F5 F 0.5657(7) 0.5932(2) 0.5063(4) 0.112(2) Uani 0.758(8) 1 d . . P . .
F6 F 0.7959(4) 0.5219(2) 0.5611(3) 0.0604(8) Uani 0.758(8) 1 d . . P . .
F7 F 1.0537(5) 0.4688(2) 0.7903(2) 0.1412(18) Uani 0.891(5) 1 d . . P . .
F8 F 1.1114(4) 0.42830(18) 0.64788(16) 0.0926(11) Uani 0.891(5) 1 d . . P . .
F9 F 1.2968(4) 0.39854(17) 0.7392(3) 0.1177(13) Uani 0.891(5) 1 d . . P . .
F1A F 0.5826(19) 0.6050(15) 0.9363(11) 0.055(4) Uiso 0.146(6) 1 d . . P . .
F2A F 0.737(2) 0.5400(13) 1.0421(11) 0.080(5) Uiso 0.146(6) 1 d . . P . .
F3A F 0.8088(19) 0.5395(13) 0.9024(11) 0.075(4) Uiso 0.146(6) 1 d . . P . .
F4A F 0.6417(12) 0.5356(10) 0.6636(7) 0.049(2) Uiso 0.242(8) 1 d . . P . .
F5A F 0.7420(14) 0.5403(9) 0.5311(7) 0.064(3) Uiso 0.242(8) 1 d . . P . .
F6A F 0.4870(8) 0.6072(6) 0.5593(5) 0.044(2) Uiso 0.242(8) 1 d . . P . .
F7A F 1.009(2) 0.4673(14) 0.7023(14) 0.067(5) Uiso 0.109(5) 1 d . . P . .
F8A F 1.1868(18) 0.4306(11) 0.7910(9) 0.037(4) Uiso 0.109(5) 1 d . . P . .
F9A F 1.267(2) 0.4007(13) 0.6665(12) 0.061(5) Uiso 0.109(5) 1 d . . P . .
H2N H 0.756(3) 1.0749(19) 0.8693(17) 0.01 Uiso 1 1 d . . . . .
H3N H 0.755(3) 1.066(2) 0.5634(17) 0.01 Uiso 1 1 d . . . . .
H4N H 1.197(3) 0.9581(19) 0.7814(17) 0.01 Uiso 1 1 d . . . . .
H1A H 0.782(2) 1.3382(18) 0.8287(14) 0.025(5) Uiso 1 1 d . . . . .
H1B H 0.659(3) 1.2774(17) 0.8072(14) 0.027(5) Uiso 1 1 d . . . . .
H2A H 0.887(3) 1.2102(18) 0.9498(15) 0.033(6) Uiso 1 1 d . . . . .
H2B H 0.695(3) 1.2615(19) 0.9662(16) 0.033(6) Uiso 1 1 d . . . . .
H5 H 0.589(3) 0.9485(19) 1.1044(16) 0.034(6) Uiso 1 1 d . . . . .
H6 H 0.566(3) 0.767(2) 1.0987(18) 0.045(7) Uiso 1 1 d . . . . .
H8 H 0.896(3) 0.688(2) 0.8751(18) 0.050(7) Uiso 1 1 d . . . . .
H9 H 0.922(3) 0.869(2) 0.8807(16) 0.039(6) Uiso 1 1 d . . . . .
H11A H 0.943(3) 1.1888(19) 0.6175(15) 0.030(5) Uiso 1 1 d . . . . .
H11B H 0.838(3) 1.313(2) 0.6568(15) 0.032(5) Uiso 1 1 d . . . . .
H12A H 0.675(3) 1.2546(19) 0.5689(16) 0.034(6) Uiso 1 1 d . . . . .
H12B H 0.603(3) 1.2480(18) 0.6739(15) 0.029(5) Uiso 1 1 d . . . . .
H15 H 0.623(3) 0.874(2) 0.7873(17) 0.041(6) Uiso 1 1 d . . . . .
H16 H 0.619(3) 0.692(2) 0.749(2) 0.058(8) Uiso 1 1 d . . . . .
H18 H 0.666(3) 0.761(2) 0.4731(19) 0.049(7) Uiso 1 1 d . . . . .
H19 H 0.676(3) 0.943(2) 0.5080(17) 0.040(6) Uiso 1 1 d . . . . .
H21A H 1.070(3) 1.261(2) 0.7669(15) 0.033(6) Uiso 1 1 d . . . . .
H21B H 1.073(3) 1.1642(17) 0.8416(15) 0.028(5) Uiso 1 1 d . . . . .
H22A H 1.300(3) 1.1023(18) 0.7383(15) 0.034(6) Uiso 1 1 d . . . . .
H22B H 1.188(3) 1.1175(18) 0.6496(16) 0.029(5) Uiso 1 1 d . . . . .
H25 H 1.050(3) 0.8021(19) 0.5599(16) 0.033(6) Uiso 1 1 d . . . . .
H26 H 1.041(3) 0.620(2) 0.5813(18) 0.044(7) Uiso 1 1 d . . . . .
H28 H 1.278(3) 0.594(2) 0.820(2) 0.056(8) Uiso 1 1 d . . . . .
H29 H 1.277(3) 0.7797(19) 0.8019(16) 0.034(6) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C23 1.237(2) . ?
O2 C13 1.239(2) . ?
O3 C3 1.235(2) . ?
N1 C21 1.464(2) . ?
N1 C1 1.465(2) . ?
N1 C11 1.469(2) . ?
N2 C3 1.328(2) . ?
N2 C2 1.455(3) . ?
N2 H2N 0.88(2) . ?
N3 C13 1.335(3) . ?
N3 C12 1.453(3) . ?
N3 H3N 0.85(2) . ?
N4 C23 1.330(2) . ?
N4 C22 1.453(2) . ?
N4 H4N 0.84(2) . ?
C1 C2 1.520(3) . ?
C1 H1A 0.97(2) . ?
C1 H1B 1.00(2) . ?
C2 H2A 0.97(2) . ?
C2 H2B 1.00(2) . ?
C3 C4 1.498(3) . ?
C4 C9 1.390(3) . ?
C4 C5 1.393(3) . ?
C5 C6 1.377(3) . ?
C5 H5 0.97(2) . ?
C6 C7 1.391(3) . ?
C6 H6 0.98(3) . ?
C7 C8 1.390(3) . ?
C7 C10 1.490(3) . ?
C8 C9 1.384(3) . ?
C8 H8 0.93(3) . ?
C9 H9 0.96(2) . ?
C10 F2A 1.161(15) . ?
C10 F1A 1.240(18) . ?
C10 F3 1.299(3) . ?
C10 F2 1.331(4) . ?
C10 F1 1.353(3) . ?
C10 F3A 1.387(14) . ?
C11 C12 1.519(3) . ?
C11 H11A 0.99(2) . ?
C11 H11B 0.99(2) . ?
C12 H12A 0.98(2) . ?
C12 H12B 0.98(2) . ?
C13 C14 1.503(3) . ?
C14 C15 1.390(3) . ?
C14 C19 1.394(3) . ?
C15 C16 1.380(3) . ?
C15 H15 1.00(2) . ?
C16 C17 1.380(3) . ?
C16 H16 0.98(3) . ?
C17 C18 1.388(3) . ?
C17 C20 1.488(3) . ?
C18 C19 1.381(3) . ?
C18 H18 0.95(3) . ?
C19 H19 0.99(2) . ?
C20 F5A 1.168(10) . ?
C20 F4 1.304(4) . ?
C20 F4A 1.340(11) . ?
C20 F5 1.345(4) . ?
C20 F6A 1.360(7) . ?
C20 F6 1.374(4) . ?
C21 C22 1.517(3) . ?
C21 H21A 0.98(2) . ?
C21 H21B 0.99(2) . ?
C22 H22A 0.99(2) . ?
C22 H22B 0.99(2) . ?
C23 C24 1.499(3) . ?
C24 C25 1.390(3) . ?
C24 C29 1.396(3) . ?
C25 C26 1.382(3) . ?
C25 H25 0.94(2) . ?
C26 C27 1.387(3) . ?
C26 H26 0.96(3) . ?
C27 C28 1.387(3) . ?
C27 C30 1.490(3) . ?
C28 C29 1.381(3) . ?
C28 H28 0.96(3) . ?
C29 H29 0.97(2) . ?
C30 F8A 1.162(12) . ?
C30 F9A 1.297(16) . ?
C30 F7 1.300(3) . ?
C30 F8 1.304(3) . ?
C30 F7A 1.312(17) . ?
C30 F9 1.327(4) . ?
F1 F2A 0.961(18) . ?
F1 F1A 1.714(17) . ?
F2 F1A 0.538(15) . ?
F2 F3A 1.526(15) . ?
F3 F3A 1.070(15) . ?
F3 F2A 1.300(17) . ?
F4 F4A 0.517(10) . ?
F4 F6A 1.662(8) . ?
F5 F6A 0.964(6) . ?
F5 F5A 1.510(11) . ?
F6 F5A 0.638(9) . ?
F7 F8A 1.088(13) . ?
F7 F7A 1.353(18) . ?
F8 F7A 1.123(19) . ?
F8 F9A 1.317(18) . ?
F9 F9A 1.093(17) . ?
F9 F8A 1.130(14) . ?

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
C21 N1 C1 109.32(14) . . ?
C21 N1 C11 110.89(14) . . ?
C1 N1 C11 110.62(15) . . ?
C3 N2 C2 121.49(16) . . ?
C3 N2 H2N 119.9(15) . . ?
C2 N2 H2N 117.0(15) . . ?
C13 N3 C12 122.79(17) . . ?
C13 N3 H3N 118.6(16) . . ?
C12 N3 H3N 118.6(16) . . ?
C23 N4 C22 122.65(16) . . ?
C23 N4 H4N 120.0(15) . . ?
C22 N4 H4N 117.2(15) . . ?
N1 C1 C2 113.10(15) . . ?
N1 C1 H1A 111.8(12) . . ?
C2 C1 H1A 108.5(12) . . ?
N1 C1 H1B 109.3(12) . . ?
C2 C1 H1B 108.7(12) . . ?
H1A C1 H1B 105.0(17) . . ?
N2 C2 C1 110.29(16) . . ?
N2 C2 H2A 109.2(13) . . ?
C1 C2 H2A 112.2(13) . . ?
N2 C2 H2B 108.9(13) . . ?
C1 C2 H2B 109.8(13) . . ?
H2A C2 H2B 106.4(18) . . ?
O3 C3 N2 121.91(19) . . ?
O3 C3 C4 120.61(17) . . ?
N2 C3 C4 117.47(16) . . ?
C9 C4 C5 119.20(19) . . ?
C9 C4 C3 122.55(17) . . ?
C5 C4 C3 118.20(17) . . ?
C6 C5 C4 120.65(19) . . ?
C6 C5 H5 119.4(13) . . ?
C4 C5 H5 119.9(13) . . ?
C5 C6 C7 120.06(19) . . ?
C5 C6 H6 120.6(15) . . ?
C7 C6 H6 119.3(15) . . ?
C8 C7 C6 119.6(2) . . ?
C8 C7 C10 120.0(2) . . ?
C6 C7 C10 120.4(2) . . ?
C9 C8 C7 120.2(2) . . ?
C9 C8 H8 120.4(16) . . ?
C7 C8 H8 119.4(16) . . ?
C8 C9 C4 120.28(19) . . ?
C8 C9 H9 120.9(14) . . ?
C4 C9 H9 118.8(14) . . ?
F2A C10 F1A 118.3(11) . . ?
F2A C10 F3 63.5(9) . . ?
F1A C10 F3 124.9(8) . . ?
F2A C10 F2 129.8(8) . . ?
F1A C10 F2 23.8(7) . . ?
F3 C10 F2 107.9(3) . . ?
F2A C10 F1 44.1(9) . . ?
F1A C10 F1 82.6(7) . . ?
F3 C10 F1 104.7(2) . . ?
F2 C10 F1 103.7(3) . . ?
F2A C10 F3A 107.7(10) . . ?
F1A C10 F3A 91.3(9) . . ?
F3 C10 F3A 46.8(6) . . ?
F2 C10 F3A 68.3(7) . . ?
F1 C10 F3A 137.6(7) . . ?
F2A C10 C7 116.2(8) . . ?
F1A C10 C7 111.8(8) . . ?
F3 C10 C7 114.3(2) . . ?
F2 C10 C7 112.1(2) . . ?
F1 C10 C7 113.3(2) . . ?
F3A C10 C7 108.0(7) . . ?
N1 C11 C12 114.68(16) . . ?
N1 C11 H11A 108.7(13) . . ?
C12 C11 H11A 106.8(13) . . ?
N1 C11 H11B 110.5(13) . . ?
C12 C11 H11B 108.1(13) . . ?
H11A C11 H11B 107.7(18) . . ?
N3 C12 C11 114.60(16) . . ?
N3 C12 H12A 107.0(13) . . ?
C11 C12 H12A 107.5(13) . . ?
N3 C12 H12B 106.1(13) . . ?
C11 C12 H12B 111.5(13) . . ?
H12A C12 H12B 110.1(18) . . ?
O2 C13 N3 122.66(18) . . ?
O2 C13 C14 119.72(17) . . ?
N3 C13 C14 117.60(16) . . ?
C15 C14 C19 118.83(19) . . ?
C15 C14 C13 117.43(17) . . ?
C19 C14 C13 123.69(18) . . ?
C16 C15 C14 120.8(2) . . ?
C16 C15 H15 118.6(14) . . ?
C14 C15 H15 120.6(14) . . ?
C15 C16 C17 120.0(2) . . ?
C15 C16 H16 121.0(16) . . ?
C17 C16 H16 118.9(16) . . ?
C16 C17 C18 119.8(2) . . ?
C16 C17 C20 120.3(2) . . ?
C18 C17 C20 119.8(2) . . ?
C19 C18 C17 120.2(2) . . ?
C19 C18 H18 118.9(16) . . ?
C17 C18 H18 120.9(16) . . ?
C18 C19 C14 120.3(2) . . ?
C18 C19 H19 122.2(14) . . ?
C14 C19 H19 117.5(14) . . ?
F5A C20 F4 118.8(5) . . ?
F5A C20 F4A 109.2(7) . . ?
F4 C20 F4A 22.5(4) . . ?
F5A C20 F5 73.4(5) . . ?
F4 C20 F5 110.1(3) . . ?
F4A C20 F5 129.3(5) . . ?
F5A C20 F6A 111.5(6) . . ?
F4 C20 F6A 77.2(4) . . ?
F4A C20 F6A 99.7(5) . . ?
F5 C20 F6A 41.7(3) . . ?
F5A C20 F6 27.6(5) . . ?
F4 C20 F6 104.8(3) . . ?
F4A C20 F6 88.3(5) . . ?
F5 C20 F6 100.5(3) . . ?
F6A C20 F6 134.8(4) . . ?
F5A C20 C17 117.3(5) . . ?
F4 C20 C17 115.9(3) . . ?
F4A C20 C17 109.5(5) . . ?
F5 C20 C17 113.3(2) . . ?
F6A C20 C17 108.2(3) . . ?
F6 C20 C17 110.8(2) . . ?
N1 C21 C22 115.33(16) . . ?
N1 C21 H21A 111.7(13) . . ?
C22 C21 H21A 107.6(13) . . ?
N1 C21 H21B 107.1(12) . . ?
C22 C21 H21B 107.7(12) . . ?
H21A C21 H21B 107.1(17) . . ?
N4 C22 C21 111.97(15) . . ?
N4 C22 H22A 108.8(13) . . ?
C21 C22 H22A 107.4(13) . . ?
N4 C22 H22B 106.0(12) . . ?
C21 C22 H22B 111.7(12) . . ?
H22A C22 H22B 110.9(18) . . ?
O1 C23 N4 122.74(18) . . ?
O1 C23 C24 119.86(17) . . ?
N4 C23 C24 117.40(16) . . ?
C25 C24 C29 119.34(19) . . ?
C25 C24 C23 117.50(17) . . ?
C29 C24 C23 123.14(18) . . ?
C26 C25 C24 120.6(2) . . ?
C26 C25 H25 118.6(14) . . ?
C24 C25 H25 120.7(14) . . ?
C25 C26 C27 119.5(2) . . ?
C25 C26 H26 120.1(15) . . ?
C27 C26 H26 120.3(15) . . ?
C26 C27 C28 120.4(2) . . ?
C26 C27 C30 120.6(2) . . ?
C28 C27 C30 119.0(2) . . ?
C29 C28 C27 120.0(2) . . ?
C29 C28 H28 118.8(17) . . ?
C27 C28 H28 121.1(16) . . ?
C28 C29 C24 120.1(2) . . ?
C28 C29 H29 119.5(13) . . ?
C24 C29 H29 120.4(13) . . ?
F8A C30 F9A 98.9(10) . . ?
F8A C30 F7 52.1(7) . . ?
F9A C30 F7 136.8(7) . . ?
F8A C30 F8 126.8(6) . . ?
F9A C30 F8 60.8(8) . . ?
F7 C30 F8 107.8(3) . . ?
F8A C30 F7A 107.5(10) . . ?
F9A C30 F7A 109.6(12) . . ?
F7 C30 F7A 62.4(8) . . ?
F8 C30 F7A 50.9(9) . . ?
F8A C30 F9 53.5(7) . . ?
F9A C30 F9 49.2(8) . . ?
F7 C30 F9 104.2(3) . . ?
F8 C30 F9 104.3(3) . . ?
F7A C30 F9 135.4(8) . . ?
F8A C30 C27 118.6(6) . . ?
F9A C30 C27 110.0(7) . . ?
F7 C30 C27 112.2(2) . . ?
F8 C30 C27 114.7(2) . . ?
F7A C30 C27 111.5(7) . . ?
F9 C30 C27 112.8(2) . . ?
F2A F1 C10 57.3(9) . . ?
F2A F1 F1A 96.8(10) . . ?
C10 F1 F1A 45.8(6) . . ?
F1A F2 C10 69(2) . . ?
F1A F2 F3A 124(2) . . ?
C10 F2 F3A 57.6(6) . . ?
F3A F3 C10 70.9(8) . . ?
F3A F3 F2A 120.7(11) . . ?
C10 F3 F2A 53.1(7) . . ?
F4A F4 C20 82.6(15) . . ?
F4A F4 F6A 135.4(16) . . ?
C20 F4 F6A 52.9(3) . . ?
F6A F5 C20 69.9(5) . . ?
F6A F5 F5A 113.8(6) . . ?
C20 F5 F5A 47.9(4) . . ?
F5A F6 C20 57.9(10) . . ?
F8A F7 C30 57.4(7) . . ?
F8A F7 F7A 109.4(10) . . ?
C30 F7 F7A 59.3(7) . . ?
F7A F8 C30 64.9(9) . . ?
F7A F8 F9A 121.5(12) . . ?
C30 F8 F9A 59.3(7) . . ?
F9A F9 F8A 114.6(11) . . ?
F9A F9 C30 64.0(9) . . ?
F8A F9 C30 55.8(6) . . ?
F2 F1A C10 88(2) . . ?
F2 F1A F1 132(2) . . ?
C10 F1A F1 51.5(6) . . ?
F1 F2A C10 78.6(11) . . ?
F1 F2A F3 136.2(15) . . ?
C10 F2A F3 63.5(8) . . ?
F3 F3A C10 62.3(8) . . ?
F3 F3A F2 108.8(11) . . ?
C10 F3A F2 54.1(5) . . ?
F4 F4A C20 74.9(15) . . ?
F6 F5A C20 94.5(12) . . ?
F6 F5A F5 151.3(14) . . ?
C20 F5A F5 58.7(5) . . ?
F5 F6A C20 68.3(4) . . ?
F5 F6A F4 108.7(6) . . ?
C20 F6A F4 49.9(3) . . ?
F8 F7A C30 64.2(9) . . ?
F8 F7A F7 116.0(13) . . ?
C30 F7A F7 58.4(7) . . ?
F7 F8A F9 138.3(12) . . ?
F7 F8A C30 70.5(7) . . ?
F9 F8A C30 70.7(8) . . ?
F9 F9A C30 66.9(9) . . ?
F9 F9A F8 118.9(13) . . ?
C30 F9A F8 59.8(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 N1 C1 C2 -68.7(2) . . . . ?
C11 N1 C1 C2 168.90(16) . . . . ?
C3 N2 C2 C1 -172.23(17) . . . . ?
N1 C1 C2 N2 -53.2(2) . . . . ?
C2 N2 C3 O3 -1.4(3) . . . . ?
C2 N2 C3 C4 177.92(16) . . . . ?
O3 C3 C4 C9 -139.0(2) . . . . ?
N2 C3 C4 C9 41.7(3) . . . . ?
O3 C3 C4 C5 38.4(3) . . . . ?
N2 C3 C4 C5 -140.90(18) . . . . ?
C9 C4 C5 C6 -1.2(3) . . . . ?
C3 C4 C5 C6 -178.68(17) . . . . ?
C4 C5 C6 C7 0.4(3) . . . . ?
C5 C6 C7 C8 0.9(3) . . . . ?
C5 C6 C7 C10 -177.02(19) . . . . ?
C6 C7 C8 C9 -1.6(3) . . . . ?
C10 C7 C8 C9 176.4(2) . . . . ?
C7 C8 C9 C4 0.8(3) . . . . ?
C5 C4 C9 C8 0.5(3) . . . . ?
C3 C4 C9 C8 177.93(18) . . . . ?
C8 C7 C10 F2A 122.2(11) . . . . ?
C6 C7 C10 F2A -59.8(11) . . . . ?
C8 C7 C10 F1A -97.8(8) . . . . ?
C6 C7 C10 F1A 80.2(8) . . . . ?
C8 C7 C10 F3 51.2(4) . . . . ?
C6 C7 C10 F3 -130.9(3) . . . . ?
C8 C7 C10 F2 -72.1(4) . . . . ?
C6 C7 C10 F2 105.9(3) . . . . ?
C8 C7 C10 F1 171.0(2) . . . . ?
C6 C7 C10 F1 -11.1(3) . . . . ?
C8 C7 C10 F3A 1.2(8) . . . . ?
C6 C7 C10 F3A 179.1(8) . . . . ?
C21 N1 C11 C12 168.05(16) . . . . ?
C1 N1 C11 C12 -70.5(2) . . . . ?
C13 N3 C12 C11 97.4(2) . . . . ?
N1 C11 C12 N3 -67.9(2) . . . . ?
C12 N3 C13 O2 -7.0(3) . . . . ?
C12 N3 C13 C14 171.18(16) . . . . ?
O2 C13 C14 C15 -16.0(3) . . . . ?
N3 C13 C14 C15 165.78(18) . . . . ?
O2 C13 C14 C19 161.37(19) . . . . ?
N3 C13 C14 C19 -16.9(3) . . . . ?
C19 C14 C15 C16 2.3(3) . . . . ?
C13 C14 C15 C16 179.81(19) . . . . ?
C14 C15 C16 C17 -1.9(3) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C15 C16 C17 C20 179.7(2) . . . . ?
C16 C17 C18 C19 1.2(3) . . . . ?
C20 C17 C18 C19 -178.5(2) . . . . ?
C17 C18 C19 C14 -0.7(3) . . . . ?
C15 C14 C19 C18 -1.1(3) . . . . ?
C13 C14 C19 C18 -178.38(19) . . . . ?
C16 C17 C20 F5A -131.9(7) . . . . ?
C18 C17 C20 F5A 47.7(7) . . . . ?
C16 C17 C20 F4 16.7(4) . . . . ?
C18 C17 C20 F4 -163.7(4) . . . . ?
C16 C17 C20 F4A -6.8(5) . . . . ?
C18 C17 C20 F4A 172.9(5) . . . . ?
C16 C17 C20 F5 145.4(4) . . . . ?
C18 C17 C20 F5 -35.0(4) . . . . ?
C16 C17 C20 F6A 101.0(4) . . . . ?
C18 C17 C20 F6A -79.4(4) . . . . ?
C16 C17 C20 F6 -102.5(3) . . . . ?
C18 C17 C20 F6 77.1(3) . . . . ?
C1 N1 C21 C22 172.19(15) . . . . ?
C11 N1 C21 C22 -65.6(2) . . . . ?
C23 N4 C22 C21 118.32(19) . . . . ?
N1 C21 C22 N4 -57.2(2) . . . . ?
C22 N4 C23 O1 1.1(3) . . . . ?
C22 N4 C23 C24 -178.11(16) . . . . ?
O1 C23 C24 C25 -18.8(3) . . . . ?
N4 C23 C24 C25 160.51(17) . . . . ?
O1 C23 C24 C29 159.56(19) . . . . ?
N4 C23 C24 C29 -21.2(3) . . . . ?
C29 C24 C25 C26 -0.6(3) . . . . ?
C23 C24 C25 C26 177.78(18) . . . . ?
C24 C25 C26 C27 -0.5(3) . . . . ?
C25 C26 C27 C28 0.9(3) . . . . ?
C25 C26 C27 C30 179.6(2) . . . . ?
C26 C27 C28 C29 -0.3(3) . . . . ?
C30 C27 C28 C29 -179.0(2) . . . . ?
C27 C28 C29 C24 -0.8(3) . . . . ?
C25 C24 C29 C28 1.2(3) . . . . ?
C23 C24 C29 C28 -177.06(18) . . . . ?
C26 C27 C30 F8A -168.7(9) . . . . ?
C28 C27 C30 F8A 9.9(9) . . . . ?
C26 C27 C30 F9A 78.7(9) . . . . ?
C28 C27 C30 F9A -102.7(9) . . . . ?
C26 C27 C30 F7 -110.9(3) . . . . ?
C28 C27 C30 F7 67.7(4) . . . . ?
C26 C27 C30 F8 12.5(4) . . . . ?
C28 C27 C30 F8 -168.9(3) . . . . ?
C26 C27 C30 F7A -43.1(10) . . . . ?
C28 C27 C30 F7A 135.5(10) . . . . ?
C26 C27 C30 F9 131.7(3) . . . . ?
C28 C27 C30 F9 -49.7(4) . . . . ?
F1A C10 F1 F2A 145.2(13) . . . . ?
F3 C10 F1 F2A 20.9(11) . . . . ?
F2 C10 F1 F2A 134.0(11) . . . . ?
F3A C10 F1 F2A 61.3(15) . . . . ?
C7 C10 F1 F2A -104.2(11) . . . . ?
F2A C10 F1 F1A -145.2(13) . . . . ?
F3 C10 F1 F1A -124.3(8) . . . . ?
F2 C10 F1 F1A -11.2(9) . . . . ?
F3A C10 F1 F1A -83.9(13) . . . . ?
C7 C10 F1 F1A 110.6(8) . . . . ?
F2A C10 F2 F1A 69(3) . . . . ?
F3 C10 F2 F1A 139(2) . . . . ?
F1 C10 F2 F1A 28(2) . . . . ?
F3A C10 F2 F1A 165(2) . . . . ?
C7 C10 F2 F1A -94(2) . . . . ?
F2A C10 F2 F3A -95.4(13) . . . . ?
F1A C10 F2 F3A -165(2) . . . . ?
F3 C10 F2 F3A -25.4(7) . . . . ?
F1 C10 F2 F3A -136.1(7) . . . . ?
C7 C10 F2 F3A 101.3(7) . . . . ?
F2A C10 F3 F3A 159.2(13) . . . . ?
F1A C10 F3 F3A 51.9(13) . . . . ?
F2 C10 F3 F3A 33.1(9) . . . . ?
F1 C10 F3 F3A 143.1(9) . . . . ?
C7 C10 F3 F3A -92.4(9) . . . . ?
F1A C10 F3 F2A -107.4(12) . . . . ?
F2 C10 F3 F2A -126.1(9) . . . . ?
F1 C10 F3 F2A -16.1(9) . . . . ?
F3A C10 F3 F2A -159.2(13) . . . . ?
C7 C10 F3 F2A 108.4(9) . . . . ?
F5A C20 F4 F4A 69.8(17) . . . . ?
F5 C20 F4 F4A 151.4(15) . . . . ?
F6A C20 F4 F4A 177.4(16) . . . . ?
F6 C20 F4 F4A 44.0(16) . . . . ?
C17 C20 F4 F4A -78.4(16) . . . . ?
F5A C20 F4 F6A -107.7(7) . . . . ?
F4A C20 F4 F6A -177.4(16) . . . . ?
F5 C20 F4 F6A -26.0(3) . . . . ?
F6 C20 F4 F6A -133.4(4) . . . . ?
C17 C20 F4 F6A 104.2(4) . . . . ?
F5A C20 F5 F6A 155.3(7) . . . . ?
F4 C20 F5 F6A 40.0(5) . . . . ?
F4A C20 F5 F6A 53.7(8) . . . . ?
F6 C20 F5 F6A 150.2(5) . . . . ?
C17 C20 F5 F6A -91.6(5) . . . . ?
F4 C20 F5 F5A -115.3(6) . . . . ?
F4A C20 F5 F5A -101.5(8) . . . . ?
F6A C20 F5 F5A -155.3(7) . . . . ?
F6 C20 F5 F5A -5.1(6) . . . . ?
C17 C20 F5 F5A 113.1(5) . . . . ?
F4 C20 F6 F5A 124.8(12) . . . . ?
F4A C20 F6 F5A 140.3(12) . . . . ?
F5 C20 F6 F5A 10.6(11) . . . . ?
F6A C20 F6 F5A 38.4(12) . . . . ?
C17 C20 F6 F5A -109.5(11) . . . . ?
F9A C30 F7 F8A 57.1(15) . . . . ?
F8 C30 F7 F8A 123.2(8) . . . . ?
F7A C30 F7 F8A 146.9(11) . . . . ?
F9 C30 F7 F8A 12.8(8) . . . . ?
C27 C30 F7 F8A -109.6(8) . . . . ?
F8A C30 F7 F7A -146.9(11) . . . . ?
F9A C30 F7 F7A -89.7(15) . . . . ?
F8 C30 F7 F7A -23.7(9) . . . . ?
F9 C30 F7 F7A -134.1(9) . . . . ?
C27 C30 F7 F7A 103.5(9) . . . . ?
F8A C30 F8 F7A 82.9(13) . . . . ?
F9A C30 F8 F7A 161.5(13) . . . . ?
F7 C30 F8 F7A 27.3(9) . . . . ?
F9 C30 F8 F7A 137.7(10) . . . . ?
C27 C30 F8 F7A -98.4(9) . . . . ?
F8A C30 F8 F9A -78.7(12) . . . . ?
F7 C30 F8 F9A -134.2(9) . . . . ?
F7A C30 F8 F9A -161.5(13) . . . . ?
F9 C30 F8 F9A -23.8(8) . . . . ?
C27 C30 F8 F9A 100.0(8) . . . . ?
F8A C30 F9 F9A 153.2(12) . . . . ?
F7 C30 F9 F9A 140.7(10) . . . . ?
F8 C30 F9 F9A 27.8(10) . . . . ?
F7A C30 F9 F9A 75.8(16) . . . . ?
C27 C30 F9 F9A -97.3(10) . . . . ?
F9A C30 F9 F8A -153.2(12) . . . . ?
F7 C30 F9 F8A -12.5(8) . . . . ?
F8 C30 F9 F8A -125.4(8) . . . . ?
F7A C30 F9 F8A -77.4(15) . . . . ?
C27 C30 F9 F8A 109.5(8) . . . . ?
F3A F2 F1A C10 16(2) . . . . ?
C10 F2 F1A F1 -29(2) . . . . ?
F3A F2 F1A F1 -14(4) . . . . ?
F2A C10 F1A F2 -125(2) . . . . ?
F3 C10 F1A F2 -49(3) . . . . ?
F1 C10 F1A F2 -152(2) . . . . ?
F3A C10 F1A F2 -14(2) . . . . ?
C7 C10 F1A F2 96(2) . . . . ?
F2A C10 F1A F1 26.9(10) . . . . ?
F3 C10 F1A F1 102.8(6) . . . . ?
F2 C10 F1A F1 152(2) . . . . ?
F3A C10 F1A F1 137.8(7) . . . . ?
C7 C10 F1A F1 -112.2(4) . . . . ?
F2A F1 F1A F2 10(4) . . . . ?
C10 F1 F1A F2 39(3) . . . . ?
F2A F1 F1A C10 -28.9(11) . . . . ?
F1A F1 F2A C10 24.4(9) . . . . ?
C10 F1 F2A F3 -29.9(14) . . . . ?
F1A F1 F2A F3 -5(2) . . . . ?
F1A C10 F2A F1 -40.1(14) . . . . ?
F3 C10 F2A F1 -157.3(11) . . . . ?
F2 C10 F2A F1 -65.5(13) . . . . ?
F3A C10 F2A F1 -141.6(9) . . . . ?
C7 C10 F2A F1 97.2(9) . . . . ?
F1A C10 F2A F3 117.2(10) . . . . ?
F2 C10 F2A F3 91.9(10) . . . . ?
F1 C10 F2A F3 157.3(11) . . . . ?
F3A C10 F2A F3 15.7(9) . . . . ?
C7 C10 F2A F3 -105.5(5) . . . . ?
F3A F3 F2A F1 10(3) . . . . ?
C10 F3 F2A F1 33.1(16) . . . . ?
F3A F3 F2A C10 -22.9(13) . . . . ?
F2A F3 F3A C10 19.2(11) . . . . ?
C10 F3 F3A F2 -28.6(7) . . . . ?
F2A F3 F3A F2 -9.4(16) . . . . ?
F2A C10 F3A F3 -19.5(12) . . . . ?
F1A C10 F3A F3 -139.8(10) . . . . ?
F2 C10 F3A F3 -146.0(9) . . . . ?
F1 C10 F3A F3 -59.3(12) . . . . ?
C7 C10 F3A F3 106.7(6) . . . . ?
F2A C10 F3A F2 126.5(9) . . . . ?
F1A C10 F3A F2 6.2(9) . . . . ?
F3 C10 F3A F2 146.0(9) . . . . ?
F1 C10 F3A F2 86.7(9) . . . . ?
C7 C10 F3A F2 -107.3(4) . . . . ?
F1A F2 F3A F3 14(3) . . . . ?
C10 F2 F3A F3 31.5(8) . . . . ?
F1A F2 F3A C10 -17(3) . . . . ?
F6A F4 F4A C20 2.9(19) . . . . ?
F5A C20 F4A F4 -119.5(15) . . . . ?
F5 C20 F4A F4 -35.5(18) . . . . ?
F6A C20 F4A F4 -2.5(16) . . . . ?
F6 C20 F4A F4 -137.7(15) . . . . ?
C17 C20 F4A F4 110.8(15) . . . . ?
C20 F6 F5A F5 -20(2) . . . . ?
F4 C20 F5A F6 -64.9(12) . . . . ?
F4A C20 F5A F6 -42.6(12) . . . . ?
F5 C20 F5A F6 -169.2(12) . . . . ?
F6A C20 F5A F6 -151.7(9) . . . . ?
C17 C20 F5A F6 82.8(11) . . . . ?
F4 C20 F5A F5 104.2(4) . . . . ?
F4A C20 F5A F5 126.6(5) . . . . ?
F6A C20 F5A F5 17.4(5) . . . . ?
F6 C20 F5A F5 169.2(12) . . . . ?
C17 C20 F5A F5 -108.1(4) . . . . ?
F6A F5 F5A F6 -2(3) . . . . ?
C20 F5 F5A F6 23(2) . . . . ?
F6A F5 F5A C20 -25.4(7) . . . . ?
F5A F5 F6A C20 19.8(5) . . . . ?
C20 F5 F6A F4 -30.0(3) . . . . ?
F5A F5 F6A F4 -10.2(8) . . . . ?
F5A C20 F6A F5 -25.5(7) . . . . ?
F4 C20 F6A F5 -141.7(5) . . . . ?
F4A C20 F6A F5 -140.7(6) . . . . ?
F6 C20 F6A F5 -43.5(7) . . . . ?
C17 C20 F6A F5 104.9(4) . . . . ?
F5A C20 F6A F4 116.2(6) . . . . ?
F4A C20 F6A F4 1.0(6) . . . . ?
F5 C20 F6A F4 141.7(5) . . . . ?
F6 C20 F6A F4 98.2(4) . . . . ?
C17 C20 F6A F4 -113.4(3) . . . . ?
F4A F4 F6A F5 34(3) . . . . ?
C20 F4 F6A F5 37.4(5) . . . . ?
F4A F4 F6A C20 -4(2) . . . . ?
F9A F8 F7A C30 18.6(12) . . . . ?
C30 F8 F7A F7 -27.9(9) . . . . ?
F9A F8 F7A F7 -9.2(19) . . . . ?
F8A C30 F7A F8 -123.5(9) . . . . ?
F9A C30 F7A F8 -17.1(12) . . . . ?
F7 C30 F7A F8 -150.4(10) . . . . ?
F9 C30 F7A F8 -68.2(13) . . . . ?
C27 C30 F7A F8 104.9(6) . . . . ?
F8A C30 F7A F7 26.9(9) . . . . ?
F9A C30 F7A F7 133.4(9) . . . . ?
F8 C30 F7A F7 150.4(10) . . . . ?
F9 C30 F7A F7 82.2(11) . . . . ?
C27 C30 F7A F7 -104.6(5) . . . . ?
F8A F7 F7A F8 0.4(17) . . . . ?
C30 F7 F7A F8 29.6(10) . . . . ?
F8A F7 F7A C30 -29.2(10) . . . . ?
C30 F7 F8A F9 -22.2(13) . . . . ?
F7A F7 F8A F9 8(2) . . . . ?
F7A F7 F8A C30 29.9(10) . . . . ?
F9A F9 F8A F7 -4(2) . . . . ?
C30 F9 F8A F7 22.2(13) . . . . ?
F9A F9 F8A C30 -26.4(12) . . . . ?
F9A C30 F8A F7 -144.4(9) . . . . ?
F8 C30 F8A F7 -84.3(9) . . . . ?
F7A C30 F8A F7 -30.5(11) . . . . ?
F9 C30 F8A F7 -164.6(9) . . . . ?
C27 C30 F8A F7 97.0(6) . . . . ?
F9A C30 F8A F9 20.2(9) . . . . ?
F7 C30 F8A F9 164.6(9) . . . . ?
F8 C30 F8A F9 80.2(8) . . . . ?
F7A C30 F8A F9 134.0(9) . . . . ?
C27 C30 F8A F9 -98.4(6) . . . . ?
F8A F9 F9A C30 24.2(10) . . . . ?
F8A F9 F9A F8 -6.6(18) . . . . ?
C30 F9 F9A F8 -30.7(9) . . . . ?
F8A C30 F9A F9 -21.5(10) . . . . ?
F7 C30 F9A F9 -63.6(14) . . . . ?
F8 C30 F9A F9 -148.8(10) . . . . ?
F7A C30 F9A F9 -133.7(10) . . . . ?
C27 C30 F9A F9 103.4(7) . . . . ?
F8A C30 F9A F8 127.3(7) . . . . ?
F7 C30 F9A F8 85.2(11) . . . . ?
F7A C30 F9A F8 15.1(10) . . . . ?
F9 C30 F9A F8 148.8(10) . . . . ?
C27 C30 F9A F8 -107.8(5) . . . . ?
F7A F8 F9A F9 13(2) . . . . ?
C30 F8 F9A F9 32.9(11) . . . . ?
F7A F8 F9A C30 -19.7(13) . . . . ?

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
N2 H2N O2 0.88(2) 2.15(2) 2.971(2) 155(2) .
N3 H3N O1 0.85(2) 2.09(3) 2.905(2) 163(2) 2_776
N4 H4N O3 0.84(2) 2.09(2) 2.921(2) 168(2) 2_777
C12 H12A F5 0.98(2) 2.58(2) 3.373(3) 137.9(17) 2_676
C12 H12A F6A 0.98(2) 2.63(2) 3.566(7) 159.2(18) 2_676
C21 H21A F7 0.98(2) 2.58(2) 3.539(3) 163.6(17) 1_565
C21 H21A F7A 0.98(2) 2.62(3) 3.544(16) 157.1(18) 1_565
C22 H22A O2 0.99(2) 2.56(2) 3.528(2) 165.5(17) 1_655

_refine_diff_density_max         0.470
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.050


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2 Ether layering'
####################################################################### 
# 
# 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_cu_mplu61_0m
_database_code_depnum_ccdc_archive 'CCDC 1587593'
_audit_update_record             
;
2017-11-25 deposited with the CCDC.
2018-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
N,N',N''-(nitrilotris(ethane-2,1-diyl))tris(3-(trifluoromethyl)benzamide)
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H27 F9 N4 O3'
_chemical_formula_weight         662.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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                   15.8131(5)
_cell_length_b                   8.3293(3)
_cell_length_c                   24.4837(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.684(2)
_cell_angle_gamma                90
_cell_volume                     3178.84(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1974
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      56.44

_exptl_crystal_description       cut-block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.107
_shelx_estimated_absorpt_T_min   0.851
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6616
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13335
_diffrn_reflns_av_unetI/netI     0.0832
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.105
_diffrn_reflns_theta_max         56.959
_diffrn_reflns_theta_full        56.959
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4257
_reflns_number_gt                2976
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0709P)²+3.5728P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4257
_refine_ls_number_parameters     454
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0646
_refine_ls_wR_factor_ref         0.1850
_refine_ls_wR_factor_gt          0.1626
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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 0.28291(17) 0.4605(4) 0.76519(10) 0.0489(8) Uani 1 1 d . . . . .
O2 O 0.49107(18) 0.0595(4) 0.86934(11) 0.0518(8) Uani 1 1 d . . . . .
O3 O 0.57716(17) 0.3725(3) 1.04387(10) 0.0444(7) Uani 1 1 d . . . . .
N1 N 0.31869(19) 0.1685(4) 0.92133(11) 0.0347(8) Uani 1 1 d . . . . .
N2 N 0.3259(2) 0.4748(4) 0.85746(13) 0.0398(9) Uani 1 1 d . . . . .
N3 N 0.3610(2) -0.0064(4) 0.82001(13) 0.0426(9) Uani 1 1 d . . . . .
N4 N 0.4975(2) 0.2348(4) 0.97466(14) 0.0370(8) Uani 1 1 d . . . . .
F1 F 0.4507(2) 0.6286(5) 0.63303(12) 0.1107(14) Uani 1 1 d . . . . .
F2 F 0.5154(4) 0.8463(4) 0.65613(14) 0.158(2) Uani 1 1 d . . . . .
F3 F 0.5816(3) 0.6310(5) 0.65638(13) 0.1091(13) Uani 1 1 d . . . . .
F4 F 0.7010(8) 0.334(2) 0.7334(11) 0.108(4) Uani 0.5 1 d . . P A 1
F5 F 0.6815(10) 0.186(5) 0.6657(7) 0.158(9) Uani 0.5 1 d . . P A 1
F6 F 0.7123(11) 0.093(5) 0.745(2) 0.221(13) Uani 0.5 1 d . . P A 1
F4A F 0.6937(8) 0.063(3) 0.6961(11) 0.123(6) Uani 0.5 1 d . . P A 2
F5A F 0.6922(10) 0.312(4) 0.6877(19) 0.189(9) Uani 0.5 1 d . . P A 2
F6A F 0.7235(7) 0.194(4) 0.7649(5) 0.117(10) Uani 0.5 1 d . . P A 2
F7 F 0.9420(2) 0.3306(7) 0.97241(16) 0.143(2) Uani 1 1 d . . . . .
F8 F 0.8943(3) 0.1945(8) 1.0322(2) 0.168(2) Uani 1 1 d . . . . .
F9 F 0.8952(2) 0.4303(7) 1.03978(18) 0.146(2) Uani 1 1 d . . . . .
C1 C 0.2648(3) 0.3089(5) 0.92404(15) 0.0393(10) Uani 1 1 d . . . . .
H1A H 0.2928 0.3805 0.9540 0.047 Uiso 1 1 calc R U . . .
H1B H 0.2093 0.2740 0.9337 0.047 Uiso 1 1 calc R U . . .
C2 C 0.2479(3) 0.4026(5) 0.87024(16) 0.0426(10) Uani 1 1 d . . . . .
H2B H 0.2234 0.3298 0.8397 0.051 Uiso 1 1 calc R U . . .
H2C H 0.2053 0.4880 0.8731 0.051 Uiso 1 1 calc R U . . .
C3 C 0.3374(3) 0.5003(5) 0.80541(15) 0.0381(10) Uani 1 1 d . . . . .
C4 C 0.4199(2) 0.5776(5) 0.79565(14) 0.0363(9) Uani 1 1 d . . . . .
C5 C 0.4290(3) 0.6024(5) 0.74110(15) 0.0418(10) Uani 1 1 d . . . . .
H5A H 0.3839 0.5722 0.7122 0.050 Uiso 1 1 calc R U . . .
C6 C 0.5026(3) 0.6704(5) 0.72816(16) 0.0466(11) Uani 1 1 d . . . . .
C7 C 0.5671(3) 0.7176(5) 0.76947(18) 0.0497(11) Uani 1 1 d . . . . .
H7A H 0.6176 0.7654 0.7606 0.060 Uiso 1 1 calc R U . . .
C8 C 0.5583(3) 0.6954(6) 0.82393(17) 0.0541(12) Uani 1 1 d . . . . .
H8A H 0.6033 0.7275 0.8526 0.065 Uiso 1 1 calc R U . . .
C9 C 0.4847(3) 0.6269(5) 0.83732(16) 0.0454(11) Uani 1 1 d . . . . .
H9A H 0.4788 0.6138 0.8750 0.054 Uiso 1 1 calc R U . . .
C10 C 0.5111(3) 0.6990(7) 0.66932(18) 0.0593(13) Uani 1 1 d . . . . .
C11 C 0.2709(3) 0.0372(5) 0.89083(16) 0.0414(10) Uani 1 1 d . . . . .
H11A H 0.2274 0.0827 0.8611 0.050 Uiso 1 1 calc R U . . .
H11B H 0.2403 -0.0234 0.9163 0.050 Uiso 1 1 calc R U . . .
C12 C 0.3276(3) -0.0775(5) 0.86534(16) 0.0448(11) Uani 1 1 d . . . . .
H12A H 0.3759 -0.1117 0.8941 0.054 Uiso 1 1 calc R U . . .
H12B H 0.2940 -0.1743 0.8520 0.054 Uiso 1 1 calc R U . . .
C13 C 0.4398(3) 0.0573(5) 0.82498(16) 0.0430(10) Uani 1 1 d . . . . .
C14 C 0.4645(3) 0.1246(5) 0.77305(16) 0.0427(10) Uani 1 1 d . . . . .
C15 C 0.5504(3) 0.1351(5) 0.76938(18) 0.0508(11) Uani 1 1 d . . . . .
H15A H 0.5924 0.1042 0.8000 0.061 Uiso 1 1 calc R U . . .
C16 C 0.5761(3) 0.1906(6) 0.7211(2) 0.0587(13) Uani 1 1 d . . . . .
C17 C 0.5158(4) 0.2361(6) 0.6764(2) 0.0614(13) Uani 1 1 d . . . . .
H17A H 0.5334 0.2718 0.6432 0.074 Uiso 1 1 calc R U . . .
C18 C 0.4300(3) 0.2293(6) 0.68011(18) 0.0573(12) Uani 1 1 d . . . . .
H18A H 0.3884 0.2633 0.6497 0.069 Uiso 1 1 calc R U . . .
C19 C 0.4039(3) 0.1732(5) 0.72799(17) 0.0497(11) Uani 1 1 d . . . . .
H19A H 0.3445 0.1679 0.7301 0.060 Uiso 1 1 calc R U . . .
C20 C 0.6694(4) 0.1952(10) 0.7163(3) 0.0806(17) Uani 1 1 d . . . . .
C21 C 0.3572(3) 0.1131(5) 0.97695(15) 0.0416(10) Uani 1 1 d . . . . .
H21A H 0.3810 0.0042 0.9739 0.050 Uiso 1 1 calc R U . . .
H21B H 0.3116 0.1050 1.0000 0.050 Uiso 1 1 calc R U . . .
C22 C 0.4274(3) 0.2210(5) 1.00587(15) 0.0403(10) Uani 1 1 d . . . . .
H22A H 0.4034 0.3289 1.0107 0.048 Uiso 1 1 calc R U . . .
H22B H 0.4495 0.1772 1.0431 0.048 Uiso 1 1 calc R U . . .
C23 C 0.5685(3) 0.3120(5) 0.99670(14) 0.0368(9) Uani 1 1 d . . . . .
C24 C 0.6406(3) 0.3219(5) 0.96468(15) 0.0387(10) Uani 1 1 d . . . . .
C25 C 0.7238(3) 0.3190(5) 0.99419(16) 0.0456(11) Uani 1 1 d . . . . .
H25A H 0.7329 0.3079 1.0334 0.055 Uiso 1 1 calc R U . . .
C26 C 0.7928(3) 0.3322(6) 0.96720(19) 0.0544(12) Uani 1 1 d . . . . .
C27 C 0.7797(3) 0.3529(7) 0.9104(2) 0.0664(14) Uani 1 1 d . . . . .
H27A H 0.8274 0.3637 0.8917 0.080 Uiso 1 1 calc R U . . .
C28 C 0.6975(4) 0.3578(7) 0.88082(19) 0.0669(15) Uani 1 1 d . . . . .
H28A H 0.6886 0.3742 0.8419 0.080 Uiso 1 1 calc R U . . .
C29 C 0.6283(3) 0.3391(5) 0.90757(16) 0.0498(11) Uani 1 1 d . . . . .
H29A H 0.5718 0.3380 0.8868 0.060 Uiso 1 1 calc R U . . .
C30 C 0.8812(4) 0.3246(9) 0.9996(3) 0.0802(17) Uani 1 1 d . . . . .
H2N H 0.357(3) 0.509(5) 0.8844(17) 0.048(13) Uiso 1 1 d . . . . .
H3N H 0.324(3) -0.009(6) 0.7841(19) 0.070(14) Uiso 1 1 d . . . . .
H4N H 0.490(2) 0.189(4) 0.9444(15) 0.027(10) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.240(4) . ?
O2 C13 1.241(4) . ?
O3 C23 1.246(4) . ?
N1 C1 1.455(5) . ?
N1 C11 1.461(5) . ?
N1 C21 1.469(5) . ?
N2 C3 1.334(5) . ?
N2 C2 1.452(5) . ?
N2 H2N 0.80(4) . ?
N3 C13 1.341(5) . ?
N3 C12 1.435(5) . ?
N3 H3N 0.97(5) . ?
N4 C23 1.328(5) . ?
N4 C22 1.453(5) . ?
N4 H4N 0.82(4) . ?
F1 C10 1.327(6) . ?
F2 C10 1.273(6) . ?
F3 C10 1.335(6) . ?
F4 C20 1.299(12) . ?
F5 C20 1.287(15) . ?
F6 C20 1.227(15) . ?
F4A C20 1.293(15) . ?
F5A C20 1.286(14) . ?
F6A C20 1.344(15) . ?
F7 C30 1.259(6) . ?
F8 C30 1.340(8) . ?
F9 C30 1.311(7) . ?
C1 C2 1.516(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2B 0.9900 . ?
C2 H2C 0.9900 . ?
C3 C4 1.509(6) . ?
C4 C5 1.383(5) . ?
C4 C9 1.382(5) . ?
C5 C6 1.378(6) . ?
C5 H5A 0.9500 . ?
C6 C7 1.368(6) . ?
C6 C10 1.488(6) . ?
C7 C8 1.376(6) . ?
C7 H7A 0.9500 . ?
C8 C9 1.384(6) . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9500 . ?
C11 C12 1.514(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.500(6) . ?
C14 C15 1.379(6) . ?
C14 C19 1.395(6) . ?
C15 C16 1.392(7) . ?
C15 H15A 0.9500 . ?
C16 C17 1.378(7) . ?
C16 C20 1.501(7) . ?
C17 C18 1.376(7) . ?
C17 H17A 0.9500 . ?
C18 C19 1.388(6) . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9500 . ?
C21 C22 1.508(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.491(6) . ?
C24 C25 1.390(6) . ?
C24 C29 1.386(5) . ?
C25 C26 1.371(6) . ?
C25 H25A 0.9500 . ?
C26 C27 1.383(6) . ?
C26 C30 1.488(7) . ?
C27 C28 1.377(7) . ?
C27 H27A 0.9500 . ?
C28 C29 1.376(6) . ?
C28 H28A 0.9500 . ?
C29 H29A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C11 111.6(3) . . ?
C1 N1 C21 111.4(3) . . ?
C11 N1 C21 109.7(3) . . ?
C3 N2 C2 121.9(3) . . ?
C3 N2 H2N 124(3) . . ?
C2 N2 H2N 113(3) . . ?
C13 N3 C12 123.4(3) . . ?
C13 N3 H3N 120(3) . . ?
C12 N3 H3N 117(3) . . ?
C23 N4 C22 119.5(3) . . ?
C23 N4 H4N 125(3) . . ?
C22 N4 H4N 115(3) . . ?
N1 C1 C2 113.1(3) . . ?
N1 C1 H1A 108.9 . . ?
C2 C1 H1A 108.9 . . ?
N1 C1 H1B 108.9 . . ?
C2 C1 H1B 108.9 . . ?
H1A C1 H1B 107.8 . . ?
N2 C2 C1 111.7(3) . . ?
N2 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
N2 C2 H2C 109.3 . . ?
C1 C2 H2C 109.3 . . ?
H2B C2 H2C 107.9 . . ?
O1 C3 N2 121.9(4) . . ?
O1 C3 C4 119.5(3) . . ?
N2 C3 C4 118.7(3) . . ?
C5 C4 C9 119.0(4) . . ?
C5 C4 C3 116.7(3) . . ?
C9 C4 C3 124.3(3) . . ?
C4 C5 C6 120.8(4) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C7 C6 C5 120.1(4) . . ?
C7 C6 C10 119.5(4) . . ?
C5 C6 C10 120.4(4) . . ?
C6 C7 C8 119.6(4) . . ?
C6 C7 H7A 120.2 . . ?
C8 C7 H7A 120.2 . . ?
C7 C8 C9 120.7(4) . . ?
C7 C8 H8A 119.6 . . ?
C9 C8 H8A 119.6 . . ?
C8 C9 C4 119.8(4) . . ?
C8 C9 H9A 120.1 . . ?
C4 C9 H9A 120.1 . . ?
F2 C10 F1 108.6(5) . . ?
F2 C10 F3 105.4(5) . . ?
F1 C10 F3 100.9(4) . . ?
F2 C10 C6 114.7(4) . . ?
F1 C10 C6 113.9(4) . . ?
F3 C10 C6 112.1(4) . . ?
N1 C11 C12 113.1(3) . . ?
N1 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
N1 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
N3 C12 C11 112.3(3) . . ?
N3 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
N3 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
O2 C13 N3 123.1(4) . . ?
O2 C13 C14 120.7(4) . . ?
N3 C13 C14 116.2(3) . . ?
C15 C14 C19 118.9(4) . . ?
C15 C14 C13 118.6(4) . . ?
C19 C14 C13 122.4(4) . . ?
C14 C15 C16 120.5(4) . . ?
C14 C15 H15A 119.7 . . ?
C16 C15 H15A 119.7 . . ?
C17 C16 C15 120.3(5) . . ?
C17 C16 C20 119.2(5) . . ?
C15 C16 C20 120.4(5) . . ?
C18 C17 C16 119.6(5) . . ?
C18 C17 H17A 120.2 . . ?
C16 C17 H17A 120.2 . . ?
C17 C18 C19 120.4(5) . . ?
C17 C18 H18A 119.8 . . ?
C19 C18 H18A 119.8 . . ?
C14 C19 C18 120.2(4) . . ?
C14 C19 H19A 119.9 . . ?
C18 C19 H19A 119.9 . . ?
F6 C20 F5 110.3(17) . . ?
F4A C20 F5A 108.1(15) . . ?
F6 C20 F4 106.6(19) . . ?
F5 C20 F4 104.6(13) . . ?
F4A C20 F6A 98.4(11) . . ?
F5A C20 F6A 107.1(14) . . ?
F6 C20 C16 113.3(9) . . ?
F5 C20 C16 112.4(9) . . ?
F4A C20 C16 111.6(8) . . ?
F5A C20 C16 115.5(9) . . ?
F4 C20 C16 109.1(7) . . ?
F6A C20 C16 114.7(7) . . ?
N1 C21 C22 113.9(3) . . ?
N1 C21 H21A 108.8 . . ?
C22 C21 H21A 108.8 . . ?
N1 C21 H21B 108.8 . . ?
C22 C21 H21B 108.8 . . ?
H21A C21 H21B 107.7 . . ?
N4 C22 C21 111.5(3) . . ?
N4 C22 H22A 109.3 . . ?
C21 C22 H22A 109.3 . . ?
N4 C22 H22B 109.3 . . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
O3 C23 N4 121.8(4) . . ?
O3 C23 C24 119.3(4) . . ?
N4 C23 C24 118.9(3) . . ?
C25 C24 C29 119.1(4) . . ?
C25 C24 C23 117.8(3) . . ?
C29 C24 C23 123.1(4) . . ?
C26 C25 C24 120.5(4) . . ?
C26 C25 H25A 119.7 . . ?
C24 C25 H25A 119.7 . . ?
C25 C26 C27 119.9(4) . . ?
C25 C26 C30 119.5(4) . . ?
C27 C26 C30 120.7(5) . . ?
C28 C27 C26 120.1(4) . . ?
C28 C27 H27A 120.0 . . ?
C26 C27 H27A 120.0 . . ?
C27 C28 C29 120.2(4) . . ?
C27 C28 H28A 119.9 . . ?
C29 C28 H28A 119.9 . . ?
C28 C29 C24 120.2(4) . . ?
C28 C29 H29A 119.9 . . ?
C24 C29 H29A 119.9 . . ?
F7 C30 F9 108.8(5) . . ?
F7 C30 F8 106.9(6) . . ?
F9 C30 F8 96.1(6) . . ?
F7 C30 C26 116.7(5) . . ?
F9 C30 C26 113.4(5) . . ?
F8 C30 C26 112.9(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N1 C1 C2 -76.2(4) . . . . ?
C21 N1 C1 C2 160.8(3) . . . . ?
C3 N2 C2 C1 150.2(4) . . . . ?
N1 C1 C2 N2 -66.0(4) . . . . ?
C2 N2 C3 O1 -1.6(6) . . . . ?
C2 N2 C3 C4 179.4(3) . . . . ?
O1 C3 C4 C5 1.2(5) . . . . ?
N2 C3 C4 C5 -179.7(4) . . . . ?
O1 C3 C4 C9 179.8(4) . . . . ?
N2 C3 C4 C9 -1.1(6) . . . . ?
C9 C4 C5 C6 2.1(6) . . . . ?
C3 C4 C5 C6 -179.2(4) . . . . ?
C4 C5 C6 C7 -1.4(6) . . . . ?
C4 C5 C6 C10 -179.0(4) . . . . ?
C5 C6 C7 C8 0.6(7) . . . . ?
C10 C6 C7 C8 178.2(4) . . . . ?
C6 C7 C8 C9 -0.4(7) . . . . ?
C7 C8 C9 C4 1.1(7) . . . . ?
C5 C4 C9 C8 -1.9(6) . . . . ?
C3 C4 C9 C8 179.5(4) . . . . ?
C7 C6 C10 F2 -62.9(7) . . . . ?
C5 C6 C10 F2 114.7(6) . . . . ?
C7 C6 C10 F1 171.1(4) . . . . ?
C5 C6 C10 F1 -11.4(7) . . . . ?
C7 C6 C10 F3 57.2(6) . . . . ?
C5 C6 C10 F3 -125.2(5) . . . . ?
C1 N1 C11 C12 154.7(3) . . . . ?
C21 N1 C11 C12 -81.4(4) . . . . ?
C13 N3 C12 C11 98.2(4) . . . . ?
N1 C11 C12 N3 -70.2(4) . . . . ?
C12 N3 C13 O2 0.4(6) . . . . ?
C12 N3 C13 C14 179.3(3) . . . . ?
O2 C13 C14 C15 23.1(6) . . . . ?
N3 C13 C14 C15 -155.8(4) . . . . ?
O2 C13 C14 C19 -158.4(4) . . . . ?
N3 C13 C14 C19 22.7(6) . . . . ?
C19 C14 C15 C16 -1.2(6) . . . . ?
C13 C14 C15 C16 177.4(4) . . . . ?
C14 C15 C16 C17 0.1(7) . . . . ?
C14 C15 C16 C20 -177.3(5) . . . . ?
C15 C16 C17 C18 1.3(7) . . . . ?
C20 C16 C17 C18 178.8(5) . . . . ?
C16 C17 C18 C19 -1.7(7) . . . . ?
C15 C14 C19 C18 0.8(6) . . . . ?
C13 C14 C19 C18 -177.7(4) . . . . ?
C17 C18 C19 C14 0.6(7) . . . . ?
C17 C16 C20 F6 -149(3) . . . . ?
C15 C16 C20 F6 28(3) . . . . ?
C17 C16 C20 F5 -24(2) . . . . ?
C15 C16 C20 F5 154(2) . . . . ?
C17 C16 C20 F4A -87.2(17) . . . . ?
C15 C16 C20 F4A 90.2(16) . . . . ?
C17 C16 C20 F5A 37(3) . . . . ?
C15 C16 C20 F5A -146(3) . . . . ?
C17 C16 C20 F4 92.0(16) . . . . ?
C15 C16 C20 F4 -90.5(16) . . . . ?
C17 C16 C20 F6A 162.0(15) . . . . ?
C15 C16 C20 F6A -20.5(17) . . . . ?
C1 N1 C21 C22 -72.4(4) . . . . ?
C11 N1 C21 C22 163.6(3) . . . . ?
C23 N4 C22 C21 -173.2(3) . . . . ?
N1 C21 C22 N4 -59.9(5) . . . . ?
C22 N4 C23 O3 0.5(6) . . . . ?
C22 N4 C23 C24 178.6(3) . . . . ?
O3 C23 C24 C25 32.6(5) . . . . ?
N4 C23 C24 C25 -145.6(4) . . . . ?
O3 C23 C24 C29 -145.2(4) . . . . ?
N4 C23 C24 C29 36.6(6) . . . . ?
C29 C24 C25 C26 -0.3(6) . . . . ?
C23 C24 C25 C26 -178.2(4) . . . . ?
C24 C25 C26 C27 1.8(7) . . . . ?
C24 C25 C26 C30 -178.5(5) . . . . ?
C25 C26 C27 C28 -1.0(8) . . . . ?
C30 C26 C27 C28 179.3(5) . . . . ?
C26 C27 C28 C29 -1.2(8) . . . . ?
C27 C28 C29 C24 2.7(7) . . . . ?
C25 C24 C29 C28 -1.9(7) . . . . ?
C23 C24 C29 C28 175.9(4) . . . . ?
C25 C26 C30 F7 177.1(6) . . . . ?
C27 C26 C30 F7 -3.1(9) . . . . ?
C25 C26 C30 F9 -55.3(8) . . . . ?
C27 C26 C30 F9 124.5(6) . . . . ?
C25 C26 C30 F8 52.7(8) . . . . ?
C27 C26 C30 F8 -127.6(6) . . . . ?

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
N2 H2N O3 0.80(4) 2.13(4) 2.925(4) 170(4) 3_667
N3 H3N O1 0.97(5) 1.92(5) 2.830(4) 154(4) 2_546
N4 H4N O2 0.82(4) 2.14(4) 2.950(4) 171(3) .

_refine_diff_density_max         0.599
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.051


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
####################################################################### 
# 
# 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_mplu59_a
_database_code_depnum_ccdc_archive 'CCDC 1816573'
_audit_update_record             
;
2018-01-12 deposited with the CCDC.
2018-01-16 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            'C8 H21 N S'
_chemical_formula_weight         163.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   12.0967(8)
_cell_length_b                   12.0967(8)
_cell_length_c                   34.713(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4399.0(7)
_cell_formula_units_Z            18
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3825
_cell_measurement_theta_min      6.62
_cell_measurement_theta_max      65.61

_exptl_crystal_description       cut-block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.110
_exptl_crystal_F_000             1656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    2.404
_shelx_estimated_absorpt_T_min   0.813
_shelx_estimated_absorpt_T_max   0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6048
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   SADABD
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11016
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         4.931
_diffrn_reflns_theta_max         66.564
_diffrn_reflns_theta_full        66.564
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             855
_reflns_number_gt                742
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0871P)²+15.6907P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         855
_refine_ls_number_parameters     87
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1616
_refine_ls_wR_factor_gt          0.1577
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
S1 S 0.0000 0.0000 0.31955(4) 0.0384(5) Uani 1 3 d S T P . .
S2 S 0.6667 0.3333 0.3333 0.0398(5) Uani 1 6 d S T P . .
N1 N 0.3333 0.3419(2) 0.4167 0.0189(7) Uani 1 2 d S T P . .
C1 C 0.3427(3) 0.2722(3) 0.38158(7) 0.0290(7) Uani 1 1 d . . . . .
C2 C 0.3388(3) 0.3304(3) 0.34315(7) 0.0286(7) Uani 1 1 d . . . . .
C3 C 0.2172(2) 0.3591(3) 0.41391(7) 0.0271(6) Uani 1 1 d . . . . .
C4 C 0.0918(3) 0.2356(3) 0.40890(10) 0.0405(8) Uani 1 1 d . . . . .
H1 H 0.422(3) 0.268(3) 0.3839(10) 0.041(9) Uiso 1 1 d . . . . .
H2 H 0.273(3) 0.188(3) 0.3845(8) 0.025(7) Uiso 1 1 d . . . . .
H3 H 0.373(3) 0.304(3) 0.3252(10) 0.048(9) Uiso 1 1 d . . . . .
H4 H 0.372(4) 0.414(5) 0.3425(12) 0.073(13) Uiso 1 1 d . . . . .
H5 H 0.256(4) 0.301(4) 0.3348(12) 0.069(12) Uiso 1 1 d . . . . .
H6 H 0.221(3) 0.411(3) 0.4384(9) 0.026(7) Uiso 1 1 d . . . . .
H7 H 0.239(3) 0.418(3) 0.3917(9) 0.033(8) Uiso 1 1 d . . . . .
H8 H 0.028(3) 0.260(3) 0.4064(9) 0.047(9) Uiso 1 1 d . . . . .
H9 H 0.075(3) 0.182(4) 0.4310(11) 0.051(10) Uiso 1 1 d . . . . .
H10 H 0.088(3) 0.189(3) 0.3848(10) 0.046(9) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.517(3) . ?
N1 C1 1.517(3) 12 ?
N1 C3 1.522(3) . ?
N1 C3 1.522(3) 12 ?
C1 C2 1.520(3) . ?
C1 H1 0.99(4) . ?
C1 H2 0.95(3) . ?
C2 H3 0.89(4) . ?
C2 H4 0.88(5) . ?
C2 H5 0.93(5) . ?
C3 C4 1.516(4) . ?
C3 H6 1.04(3) . ?
C3 H7 0.99(3) . ?
C4 H8 0.96(4) . ?
C4 H9 0.96(4) . ?
C4 H10 1.00(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C1 107.3(3) . 12 ?
C1 N1 C3 110.82(14) . . ?
C1 N1 C3 110.70(15) 12 . ?
C1 N1 C3 110.71(15) . 12 ?
C1 N1 C3 110.81(14) 12 12 ?
C3 N1 C3 106.6(3) . 12 ?
N1 C1 C2 114.8(2) . . ?
N1 C1 H1 108(2) . . ?
C2 C1 H1 110.4(19) . . ?
N1 C1 H2 103.8(18) . . ?
C2 C1 H2 112.0(17) . . ?
H1 C1 H2 108(3) . . ?
C1 C2 H3 108(2) . . ?
C1 C2 H4 117(3) . . ?
H3 C2 H4 112(3) . . ?
C1 C2 H5 112(3) . . ?
H3 C2 H5 105(3) . . ?
H4 C2 H5 102(3) . . ?
C4 C3 N1 114.2(2) . . ?
C4 C3 H6 113.8(16) . . ?
N1 C3 H6 105.5(15) . . ?
C4 C3 H7 113.2(18) . . ?
N1 C3 H7 102.3(17) . . ?
H6 C3 H7 107(2) . . ?
C3 C4 H8 106(2) . . ?
C3 C4 H9 110(2) . . ?
H8 C4 H9 111(3) . . ?
C3 C4 H10 113(2) . . ?
H8 C4 H10 106(3) . . ?
H9 C4 H10 110(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C1 C2 173.9(3) 12 . . . ?
C3 N1 C1 C2 52.9(3) . . . . ?
C3 N1 C1 C2 -65.1(3) 12 . . . ?
C1 N1 C3 C4 56.6(3) . . . . ?
C1 N1 C3 C4 -62.3(3) 12 . . . ?
C3 N1 C3 C4 177.1(3) 12 . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H10 S1 1.00(4) 3.01(4) 3.976(3) 164(3) .

_refine_diff_density_max         0.939
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.065

