# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_15
_database_code_depnum_ccdc_archive 'CCDC 2110085'
loop_
_audit_author_name
_audit_author_address
'Graham Tizzard'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2021-09-15 deposited with the CCDC.	2022-04-25 downloaded from the CCDC.
;

#2018ncs0087z

_audit_creation_date             2021-09-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H21 N5 O3'
_chemical_formula_sum            'C16 H21 N5 O3'
_chemical_formula_weight         331.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H21 N5 O3'
_chemical_oxdiff_usercomment     AKE-017
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   19.378(2)
_cell_length_b                   4.9594(2)
_cell_length_c                   18.3832(15)
_cell_angle_alpha                90
_cell_angle_beta                 116.058(12)
_cell_angle_gamma                90
_cell_volume                     1587.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4308
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.8620
_cell_measurement_theta_min      3.1440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_recrystallization_method 
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         2.467
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -99.00  15.00   1.00    7.50    --   -9.70 -38.00 -90.00  114
  2  ω    -99.00  15.00   1.00    7.50    --   -9.70 -38.00  30.00  114
  3  ω    -34.00  80.00   1.00    7.50    --   -9.70  38.00  60.00  114
  4  ω    -34.00  27.00   1.00    7.50    --   -9.70  38.00 -30.00   61
;
_diffrn_measurement_device       'four-circle κ goniometer'
_diffrn_measurement_device_details 'Rigaku, AFC12 κ goniometer'
_diffrn_measurement_device_type  
'Rigaku FRE+ equipped with HF Varimax confocal mirrors and an AFC12 goniometer and HG Saturn 724+ detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0400934000
_diffrn_orient_matrix_UB_12      -0.0249403000
_diffrn_orient_matrix_UB_13      -0.0172665000
_diffrn_orient_matrix_UB_21      0.0028899000
_diffrn_orient_matrix_UB_22      -0.0794281000
_diffrn_orient_matrix_UB_23      -0.0306537000
_diffrn_orient_matrix_UB_31      0.0066380000
_diffrn_orient_matrix_UB_32      -0.1162516000
_diffrn_orient_matrix_UB_33      0.0246280000
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2475
_reflns_number_total             3640
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3640
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0542
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0720P)²+0.1133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1447
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.70514(8) 0.2305(3) 0.66304(7) 0.0294(3) Uani 1 1 d . . . . .
O2 O 0.59913(8) 0.0591(2) 0.57283(7) 0.0296(3) Uani 1 1 d . . . . .
O3 O 1.00696(8) 0.9243(3) 0.83775(8) 0.0338(4) Uani 1 1 d . . . . .
N1 N 0.63381(9) 0.2268(3) 0.62622(8) 0.0238(4) Uani 1 1 d . . . . .
N2 N 0.70276(10) 0.6144(3) 0.76208(9) 0.0250(4) Uani 1 1 d . . . . .
H2 H 0.7311(12) 0.519(4) 0.7495(12) 0.030 Uiso 1 1 d . U . . .
N3 N 0.87059(9) 0.7264(3) 0.84577(8) 0.0244(4) Uani 1 1 d . . . . .
N4 N 0.25198(9) 0.7112(3) 0.51537(9) 0.0287(4) Uani 1 1 d . . . . .
N5 N 0.26075(9) 0.4894(3) 0.47665(9) 0.0256(4) Uani 1 1 d . . . . .
C1 C 0.62670(11) 0.6069(3) 0.71201(10) 0.0222(4) Uani 1 1 d . . . . .
C2 C 0.59005(11) 0.4239(3) 0.64620(10) 0.0220(4) Uani 1 1 d . . . . .
C3 C 0.51080(11) 0.4198(3) 0.59927(10) 0.0224(4) Uani 1 1 d . . . . .
H3 H 0.489800 0.294408 0.557596 0.027 Uiso 1 1 calc R U . . .
C4 C 0.46209(11) 0.5972(3) 0.61277(10) 0.0219(4) Uani 1 1 d . . . . .
C5 C 0.49794(11) 0.7834(3) 0.67649(10) 0.0237(4) Uani 1 1 d . . . . .
H5 H 0.467446 0.907573 0.686939 0.028 Uiso 1 1 calc R U . . .
C6 C 0.57546(11) 0.7889(3) 0.72342(10) 0.0230(4) Uani 1 1 d . . . . .
H6 H 0.595619 0.916665 0.764492 0.028 Uiso 1 1 calc R U . . .
C7 C 0.73619(11) 0.8097(4) 0.82748(10) 0.0252(4) Uani 1 1 d . . . . .
H7A H 0.705981 0.814608 0.857813 0.030 Uiso 1 1 calc R U . . .
H7B H 0.734267 0.987525 0.804671 0.030 Uiso 1 1 calc R U . . .
C8 C 0.81831(11) 0.7420(4) 0.88408(10) 0.0270(4) Uani 1 1 d . . . . .
H8A H 0.837606 0.877267 0.926451 0.032 Uiso 1 1 calc R U . . .
H8B H 0.819124 0.570035 0.909592 0.032 Uiso 1 1 calc R U . . .
C9 C 0.94818(11) 0.6740(4) 0.90909(11) 0.0286(4) Uani 1 1 d . . . . .
H9A H 0.948957 0.500371 0.933735 0.034 Uiso 1 1 calc R U . . .
H9B H 0.961544 0.810725 0.950828 0.034 Uiso 1 1 calc R U . . .
C10 C 1.00709(12) 0.6745(4) 0.87644(12) 0.0336(5) Uani 1 1 d . . . . .
H10A H 1.057627 0.643887 0.920474 0.040 Uiso 1 1 calc R U . . .
H10B H 0.996220 0.528394 0.837855 0.040 Uiso 1 1 calc R U . . .
C11 C 0.93208(11) 0.9676(4) 0.77395(11) 0.0293(5) Uani 1 1 d . . . . .
H11A H 0.919819 0.822877 0.734723 0.035 Uiso 1 1 calc R U . . .
H11B H 0.931652 1.135468 0.746697 0.035 Uiso 1 1 calc R U . . .
C12 C 0.87176(12) 0.9790(4) 0.80446(11) 0.0271(4) Uani 1 1 d . . . . .
H12A H 0.882377 1.128880 0.841755 0.033 Uiso 1 1 calc R U . . .
H12B H 0.821802 1.008584 0.759354 0.033 Uiso 1 1 calc R U . . .
C13 C 0.37881(11) 0.5933(3) 0.56478(10) 0.0218(4) Uani 1 1 d . . . . .
C14 C 0.32343(11) 0.7704(4) 0.56847(11) 0.0273(4) Uani 1 1 d . . . . .
H14 H 0.335688 0.914259 0.604450 0.033 Uiso 1 1 calc R U . . .
C15 C 0.33463(11) 0.4156(4) 0.50393(10) 0.0243(4) Uani 1 1 d . . . . .
H15 H 0.352896 0.270798 0.485281 0.029 Uiso 1 1 calc R U . . .
C16 C 0.19506(11) 0.3719(4) 0.40973(11) 0.0320(5) Uani 1 1 d . . . . .
H16A H 0.149855 0.399105 0.417801 0.048 Uiso 1 1 calc R U . . .
H16B H 0.203444 0.182183 0.406945 0.048 Uiso 1 1 calc R U . . .
H16C H 0.188322 0.456535 0.360079 0.048 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 N1 1.244(2) . ?
O2 N1 1.2358(19) . ?
O3 C10 1.428(2) . ?
O3 C11 1.425(2) . ?
N1 C2 1.443(2) . ?
N2 H2 0.83(2) . ?
N2 C1 1.352(2) . ?
N2 C7 1.456(2) . ?
N3 C8 1.468(2) . ?
N3 C9 1.465(2) . ?
N3 C12 1.470(2) . ?
N4 N5 1.361(2) . ?
N4 C14 1.330(2) . ?
N5 C15 1.343(2) . ?
N5 C16 1.448(2) . ?
C1 C2 1.427(2) . ?
C1 C6 1.424(2) . ?
C2 C3 1.393(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(2) . ?
C4 C5 1.412(2) . ?
C4 C13 1.460(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.365(3) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.508(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.505(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.503(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.411(3) . ?
C13 C15 1.386(2) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C11 O3 C10 108.59(14) . . ?
O1 N1 C2 119.24(14) . . ?
O2 N1 O1 121.90(14) . . ?
O2 N1 C2 118.86(16) . . ?
C1 N2 H2 116.8(14) . . ?
C1 N2 C7 122.46(16) . . ?
C7 N2 H2 120.0(15) . . ?
C8 N3 C12 111.93(14) . . ?
C9 N3 C8 108.17(14) . . ?
C9 N3 C12 108.57(15) . . ?
C14 N4 N5 103.49(15) . . ?
N4 N5 C16 120.29(16) . . ?
C15 N5 N4 112.49(15) . . ?
C15 N5 C16 127.05(16) . . ?
N2 C1 C2 125.59(16) . . ?
N2 C1 C6 120.30(16) . . ?
C6 C1 C2 114.11(17) . . ?
C1 C2 N1 121.14(17) . . ?
C3 C2 N1 116.34(15) . . ?
C3 C2 C1 122.49(16) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 122.04(16) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 115.92(17) . . ?
C3 C4 C13 122.73(16) . . ?
C5 C4 C13 121.35(16) . . ?
C4 C5 H5 118.6 . . ?
C6 C5 C4 122.77(17) . . ?
C6 C5 H5 118.6 . . ?
C1 C6 H6 118.7 . . ?
C5 C6 C1 122.63(16) . . ?
C5 C6 H6 118.7 . . ?
N2 C7 H7A 109.2 . . ?
N2 C7 H7B 109.2 . . ?
N2 C7 C8 111.92(15) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
N3 C8 C7 114.98(14) . . ?
N3 C8 H8A 108.5 . . ?
N3 C8 H8B 108.5 . . ?
C7 C8 H8A 108.5 . . ?
C7 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
N3 C9 H9A 109.2 . . ?
N3 C9 H9B 109.2 . . ?
N3 C9 C10 112.10(15) . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
O3 C10 C9 111.36(16) . . ?
O3 C10 H10A 109.4 . . ?
O3 C10 H10B 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
O3 C11 H11A 109.2 . . ?
O3 C11 H11B 109.2 . . ?
O3 C11 C12 112.09(15) . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
N3 C12 C11 110.58(15) . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C14 C13 C4 128.67(16) . . ?
C15 C13 C4 128.53(16) . . ?
C15 C13 C14 102.79(17) . . ?
N4 C14 C13 113.32(16) . . ?
N4 C14 H14 123.3 . . ?
C13 C14 H14 123.3 . . ?
N5 C15 C13 107.89(16) . . ?
N5 C15 H15 126.1 . . ?
C13 C15 H15 126.1 . . ?
N5 C16 H16A 109.5 . . ?
N5 C16 H16B 109.5 . . ?
N5 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
O1 N1 C2 C1 -5.5(2) . . . . ?
O1 N1 C2 C3 176.02(14) . . . . ?
O2 N1 C2 C1 174.49(14) . . . . ?
O2 N1 C2 C3 -3.9(2) . . . . ?
O3 C11 C12 N3 -59.2(2) . . . . ?
N1 C2 C3 C4 179.39(15) . . . . ?
N2 C1 C2 N1 -1.3(3) . . . . ?
N2 C1 C2 C3 177.04(16) . . . . ?
N2 C1 C6 C5 -177.56(16) . . . . ?
N2 C7 C8 N3 58.6(2) . . . . ?
N3 C9 C10 O3 57.5(2) . . . . ?
N4 N5 C15 C13 0.5(2) . . . . ?
N5 N4 C14 C13 0.5(2) . . . . ?
C1 N2 C7 C8 168.69(15) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C2 C1 C6 C5 1.5(2) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C2 C3 C4 C13 -179.21(15) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
C3 C4 C13 C14 -175.68(17) . . . . ?
C3 C4 C13 C15 3.9(3) . . . . ?
C4 C5 C6 C1 0.0(3) . . . . ?
C4 C13 C14 N4 179.41(16) . . . . ?
C4 C13 C15 N5 -179.82(16) . . . . ?
C5 C4 C13 C14 4.6(3) . . . . ?
C5 C4 C13 C15 -175.89(16) . . . . ?
C6 C1 C2 N1 179.74(15) . . . . ?
C6 C1 C2 C3 -1.9(2) . . . . ?
C7 N2 C1 C2 179.21(15) . . . . ?
C7 N2 C1 C6 -1.9(2) . . . . ?
C8 N3 C9 C10 -175.88(15) . . . . ?
C8 N3 C12 C11 173.70(15) . . . . ?
C9 N3 C8 C7 176.97(15) . . . . ?
C9 N3 C12 C11 54.37(19) . . . . ?
C10 O3 C11 C12 59.84(19) . . . . ?
C11 O3 C10 C9 -58.29(19) . . . . ?
C12 N3 C8 C7 57.4(2) . . . . ?
C12 N3 C9 C10 -54.21(19) . . . . ?
C13 C4 C5 C6 178.74(15) . . . . ?
C14 N4 N5 C15 -0.65(19) . . . . ?
C14 N4 N5 C16 -176.17(15) . . . . ?
C14 C13 C15 N5 -0.19(18) . . . . ?
C15 C13 C14 N4 -0.2(2) . . . . ?
C16 N5 C15 C13 175.70(16) . . . . ?

_olex2_date_sample_data_collection 2018-02-07
_olex2_date_sample_submission    2018-01-26
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id AKE-017
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.303
_oxdiff_exptl_absorpt_empirical_full_min 0.693
####################################################################### 
# 
# 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_17
_database_code_depnum_ccdc_archive 'CCDC 2110086'
loop_
_audit_author_name
_audit_author_address
'Graham Tizzard'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2021-09-15 deposited with the CCDC.	2022-04-25 downloaded from the CCDC.
;

#2018ncs0433y

_audit_creation_date             2021-09-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H19 N3 O3 S'
_chemical_formula_sum            'C16 H19 N3 O3 S'
_chemical_formula_weight         333.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H19 N3 O3 S'
_chemical_oxdiff_usercomment     AKE-019
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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.2068(2)
_cell_length_b                   15.1888(3)
_cell_length_c                   15.2406(2)
_cell_angle_alpha                74.263(2)
_cell_angle_beta                 85.817(2)
_cell_angle_gamma                76.699(2)
_cell_volume                     1562.57(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    31305
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.2840
_cell_measurement_theta_min      3.0010
_shelx_estimated_absorpt_T_max   0.872
_shelx_estimated_absorpt_T_min   0.689
_exptl_absorpt_coefficient_mu    2.010
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of DCM and hexane  by slow evaporation'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28801
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.239
_diffrn_reflns_theta_min         3.013
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00  89.00   0.50    0.50    --    0.00  60.00-120.00  356
  2  ω    -89.00  89.00   0.50    0.50    --    0.00  43.00   0.00  356
  3  ω   -179.00  -1.00   0.50    2.00    --  -90.00  29.00 120.00  356
  4  ω   -179.00  -1.00   0.50    2.00    --  -90.00  60.00-150.00  356
  5  ω   -179.00  -1.00   0.50    2.00    --  -90.00  57.00  30.00  356
  6  ω   -179.00  -1.00   0.50    2.00    --  -90.00  60.00  90.00  356
  7  ω   -179.00  -1.00   0.50    2.00    --  -90.00  60.00 -90.00  356
  8  ω   -179.00  -1.00   0.50    2.00    --  -90.00  60.00 -90.00  356
  9  ω   -179.00  -1.00   0.50    2.00    --  -90.00  14.00 -60.00  356
 10  ω   -179.00  -1.00   0.50    2.00    --  -90.00  60.00-150.00  356
 11  ω   -179.00  -1.00   0.50    2.00    --  -90.00  60.00 -30.00  356
 12  ω   -179.00  -1.00   0.50    2.00    --  -90.00  43.00-120.00  356
 13  ω   -179.00  -1.00   0.50    2.00    --  -90.00  29.00  30.00  356
 14  ω   -179.00  -1.00   0.50    2.00    --  -90.00  60.00-180.00  356
 15  ω   -179.00  -1.00   0.50    2.00    --  -90.00  60.00 -60.00  356
 16  ω   -179.00  -1.00   0.50    2.00    --  -90.00  60.00 120.00  356
 17  ω    -89.00  89.00   0.50    0.50    --    0.00  14.00  30.00  356
 18  ω    -89.00  27.00   0.50    0.50    --    0.00  29.00-150.00  232
 19  ω    -89.00  89.00   0.50    0.50    --    0.00  57.00 -60.00  356
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_details 'Rigaku, AFC11 quarter χ goniometer'
_diffrn_measurement_device_type  
'Rigaku 007HF equipped with Varimax confocal mirrors and an AFC11 goniometer and HyPix 6000 detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0269075000
_diffrn_orient_matrix_UB_12      0.0008362000
_diffrn_orient_matrix_UB_13      0.1010044000
_diffrn_orient_matrix_UB_21      0.0829128000
_diffrn_orient_matrix_UB_22      -0.1064671000
_diffrn_orient_matrix_UB_23      0.0287822000
_diffrn_orient_matrix_UB_31      0.2016363000
_diffrn_orient_matrix_UB_32      0.0181160000
_diffrn_orient_matrix_UB_33      0.0003554000
_diffrn_radiation_collimation    'Varimax focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Rotating anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'Rigaku 007 HF'
_diffrn_source_voltage           40.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5314
_reflns_number_total             5671
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     495
_refine_ls_number_reflns         5671
_refine_ls_number_restraints     1040
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0561P)²+0.5921P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1054
_refine_special_details          
'Disordered thiophene moities (ca. 69:31 and 90:10)have had distance restraints applied throughout. H-atoms bonded to N-atoms have been located in the difference map and refined with a riding model and distance restraint.  Anisotropic and rigid bond restraints have been applied throughout.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 N52-H52 = N2-H2
 0.86 with sigma of 0.01
 C15A-C16A \\sim C15B-C16B
 with sigma of 0.02
 C13-C15A \\sim C13-C15B
 with sigma of 0.04
 C13-C16A \\sim C13-C16B
 with sigma of 0.04
 C65A-C66A \\sim C65B-C66B
 with sigma of 0.02
 C63-C65A \\sim C63-C65B
 with sigma of 0.04
 C63-C66A \\sim C63-C66B
 with sigma of 0.04
 S1A-C13 \\sim S1B-C13
 with sigma of 0.02
 S1A-C16A \\sim S1B-C16B
 with sigma of 0.02
 C14A-C13 \\sim C14B-C13
 with sigma of 0.02
 C14A-C15A \\sim C14B-C15B
 with sigma of 0.02
 S1A-C15A \\sim S1B-C15B
 with sigma of 0.04
 C14A-C16A \\sim C14B-C16B
 with sigma of 0.04
 S51A-C63 \\sim S51B-C63
 with sigma of 0.02
 S51A-C66A \\sim S51B-C66B
 with sigma of 0.02
 C64A-C63 \\sim C64B-C63
 with sigma of 0.02
 C64A-C65A \\sim C64B-C65B
 with sigma of 0.02
 S51A-C65A \\sim S51B-C65B
 with sigma of 0.04
 C64A-C66A \\sim C64B-C66B
 with sigma of 0.04
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 S51B, C64A, C63, C64B, S51A, C65B, C66A, C66B, C65A, C13, C14B, S1A, C15B,
 C16A, C15A, C16B, S1B, C14A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Sof(S1B)=Sof(C14B)=Sof(H14B)=Sof(C15B)=Sof(H15B)=Sof(C16B)=Sof(H16B)=1-FVAR(1)
 Sof(S1A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=FVAR(1)
 Sof(S51B)=Sof(C64B)=Sof(H64B)=Sof(C65B)=Sof(H65B)=Sof(C66B)=Sof(H66B)=1-FVAR(2)
 Sof(S51A)=Sof(C64A)=Sof(H64A)=Sof(C65A)=Sof(H65A)=Sof(C66A)=Sof(H66A)=FVAR(2)
7.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B), C57(H57A,H57B), C58(H58A,H58B), C59(H59A,H59B), C60(H60A,H60B),
  C61(H61A,H61B), C62(H62A,H62B)
7.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C5(H5), C14A(H14A), C14B(H14B), C15A(H15A), C15B(H15B),
 C16A(H16A), C16B(H16B), C53(H53), C56(H56), C55(H55), C64A(H64A), C64B(H64B),
 C65A(H65A), C65B(H65B), C66A(H66A), C66B(H66B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1A S 0.31884(18) 0.14977(7) 0.29492(9) 0.0263(3) Uani 0.687(2) 1 d D U P A 1
S1B S 0.0446(6) 0.2236(3) 0.1535(3) 0.0228(6) Uani 0.313(2) 1 d D U P A 2
O1 O 0.06541(16) 0.57452(8) 0.03985(7) 0.0292(3) Uani 1 1 d . U . . .
O2 O 0.01503(17) 0.66818(7) 0.12806(7) 0.0288(3) Uani 1 1 d . U . . .
O3 O -0.32719(16) 0.92673(8) 0.28397(8) 0.0307(3) Uani 1 1 d . U . . .
N1 N 0.05600(18) 0.58764(9) 0.11699(8) 0.0224(3) Uani 1 1 d . U . . .
N2 N 0.12866(19) 0.60134(9) 0.29858(9) 0.0249(3) Uani 1 1 d D U . . .
H2 H 0.083(3) 0.6510(9) 0.2571(10) 0.030 Uiso 1 1 d D U . . .
N3 N 0.00244(18) 0.77829(9) 0.32272(9) 0.0244(3) Uani 1 1 d . U . . .
C4 C 0.1446(2) 0.33879(10) 0.24995(10) 0.0220(3) Uani 1 1 d . U . . .
C3 C 0.1035(2) 0.42017(10) 0.17982(10) 0.0214(3) Uani 1 1 d . U . . .
H3 H 0.081329 0.416393 0.120395 0.026 Uiso 1 1 calc R U . . .
C2 C 0.0941(2) 0.50778(10) 0.19516(10) 0.0213(3) Uani 1 1 d . U . . .
C1 C 0.1276(2) 0.51863(10) 0.28220(10) 0.0221(3) Uani 1 1 d . U . . .
C6 C 0.1673(2) 0.43367(11) 0.35281(10) 0.0240(3) Uani 1 1 d . U . . .
H6 H 0.189509 0.436252 0.412648 0.029 Uiso 1 1 calc R U . . .
C5 C 0.1743(2) 0.34845(11) 0.33713(10) 0.0241(3) Uani 1 1 d . U . . .
H5 H 0.200189 0.293815 0.386640 0.029 Uiso 1 1 calc R U . . .
C13 C 0.1643(2) 0.24599(10) 0.23353(10) 0.0231(3) Uani 1 1 d D U . . .
C14A C 0.0800(11) 0.2247(6) 0.1663(5) 0.0255(10) Uani 0.687(2) 1 d D U P A 1
H14A H -0.007727 0.269455 0.123987 0.031 Uiso 0.687(2) 1 calc R U P A 1
C14B C 0.292(2) 0.1657(8) 0.2788(9) 0.0306(19) Uani 0.313(2) 1 d D U P A 2
H14B H 0.371538 0.163218 0.326980 0.037 Uiso 0.313(2) 1 calc R U P A 2
C15A C 0.1377(10) 0.1287(4) 0.1667(4) 0.0258(9) Uani 0.687(2) 1 d D U P A 1
H15A H 0.090684 0.101709 0.125907 0.031 Uiso 0.687(2) 1 calc R U P A 1
C15B C 0.290(2) 0.0880(10) 0.2444(11) 0.031(2) Uani 0.313(2) 1 d D U P A 2
H15B H 0.368486 0.027372 0.267246 0.037 Uiso 0.313(2) 1 calc R U P A 2
C16A C 0.2691(9) 0.0795(4) 0.2329(5) 0.0249(9) Uani 0.687(2) 1 d D U P A 1
H16A H 0.325531 0.014608 0.243137 0.030 Uiso 0.687(2) 1 calc R U P A 1
C16B C 0.164(2) 0.1092(7) 0.1751(10) 0.0225(19) Uani 0.313(2) 1 d D U P A 2
H16B H 0.145665 0.066104 0.143322 0.027 Uiso 0.313(2) 1 calc R U P A 2
C7 C 0.1612(2) 0.61297(11) 0.38735(10) 0.0265(3) Uani 1 1 d . U . . .
H7A H 0.284591 0.572495 0.411765 0.032 Uiso 1 1 calc R U . . .
H7B H 0.058672 0.594780 0.430562 0.032 Uiso 1 1 calc R U . . .
C8 C 0.1631(2) 0.71569(11) 0.37625(11) 0.0277(3) Uani 1 1 d . U . . .
H8A H 0.158113 0.727644 0.437176 0.033 Uiso 1 1 calc R U . . .
H8B H 0.283587 0.728906 0.345866 0.033 Uiso 1 1 calc R U . . .
C9 C 0.0169(2) 0.87658(11) 0.29978(11) 0.0290(3) Uani 1 1 d . U . . .
H9A H 0.138492 0.883457 0.266894 0.035 Uiso 1 1 calc R U . . .
H9B H 0.016184 0.896703 0.356409 0.035 Uiso 1 1 calc R U . . .
C10 C -0.1482(2) 0.93780(11) 0.24078(12) 0.0315(4) Uani 1 1 d . U . . .
H10A H -0.139747 1.004242 0.228037 0.038 Uiso 1 1 calc R U . . .
H10B H -0.140177 0.921300 0.181874 0.038 Uiso 1 1 calc R U . . .
C11 C -0.3373(2) 0.83048(11) 0.30591(11) 0.0271(3) Uani 1 1 d . U . . .
H11A H -0.327675 0.809754 0.249195 0.033 Uiso 1 1 calc R U . . .
H11B H -0.462038 0.823233 0.335179 0.033 Uiso 1 1 calc R U . . .
C12 C -0.1800(2) 0.76992(11) 0.36903(10) 0.0258(3) Uani 1 1 d . U . . .
H12A H -0.187695 0.790430 0.425806 0.031 Uiso 1 1 calc R U . . .
H12B H -0.192239 0.703808 0.385243 0.031 Uiso 1 1 calc R U . . .
S51A S 0.82102(9) 0.11900(4) 0.36950(4) 0.02974(17) Uani 0.901(2) 1 d D U P B 1
S51B S 0.562(2) 0.1963(9) 0.4865(8) 0.0239(19) Uani 0.099(2) 1 d D U P B 2
O51 O 0.69064(19) 0.53704(8) 0.42074(7) 0.0344(3) Uani 1 1 d . U . . .
O52 O 0.60631(17) 0.63710(7) 0.29159(7) 0.0298(3) Uani 1 1 d . U . . .
O53 O 0.24669(17) 0.94482(8) 0.04931(8) 0.0324(3) Uani 1 1 d . U . . .
N51 N 0.64708(18) 0.55481(9) 0.33971(8) 0.0243(3) Uani 1 1 d . U . . .
N52 N 0.59305(19) 0.57985(9) 0.14494(8) 0.0239(3) Uani 1 1 d D U . . .
H52 H 0.571(3) 0.6282(9) 0.1658(12) 0.029 Uiso 1 1 d D U . . .
N53 N 0.47115(18) 0.76540(8) 0.04256(8) 0.0228(3) Uani 1 1 d . U . . .
C54 C 0.6675(2) 0.31180(10) 0.33019(10) 0.0222(3) Uani 1 1 d . U . . .
C53 C 0.6688(2) 0.38923(10) 0.36057(10) 0.0229(3) Uani 1 1 d . U . . .
H53 H 0.688009 0.381478 0.423467 0.027 Uiso 1 1 calc R U . . .
C52 C 0.6425(2) 0.47911(10) 0.30073(10) 0.0219(3) Uani 1 1 d . U . . .
C51 C 0.6152(2) 0.49505(10) 0.20574(10) 0.0214(3) Uani 1 1 d . U . . .
C56 C 0.6171(2) 0.41350(10) 0.17669(10) 0.0230(3) Uani 1 1 d . U . . .
H56 H 0.600592 0.419806 0.113833 0.028 Uiso 1 1 calc R U . . .
C55 C 0.6418(2) 0.32622(10) 0.23606(10) 0.0233(3) Uani 1 1 d . U . . .
H55 H 0.641630 0.273892 0.213264 0.028 Uiso 1 1 calc R U . . .
C63 C 0.6832(2) 0.21809(10) 0.39365(10) 0.0236(3) Uani 1 1 d D U . . .
C64A C 0.5887(10) 0.1956(4) 0.4733(4) 0.0278(9) Uani 0.901(2) 1 d D U P B 1
H64A H 0.506789 0.241234 0.498635 0.033 Uiso 0.901(2) 1 calc R U P B 1
C64B C 0.797(4) 0.1445(12) 0.3732(18) 0.038(5) Uani 0.099(2) 1 d D U P B 2
H64B H 0.880680 0.147824 0.321865 0.045 Uiso 0.099(2) 1 calc R U P B 2
C65A C 0.6222(4) 0.09676(16) 0.51675(17) 0.0261(5) Uani 0.901(2) 1 d D U P B 1
H65A H 0.564998 0.069728 0.572694 0.031 Uiso 0.901(2) 1 calc R U P B 1
C65B C 0.778(4) 0.0581(12) 0.4393(15) 0.025(4) Uani 0.099(2) 1 d D U P B 2
H65B H 0.835047 -0.003286 0.434279 0.030 Uiso 0.099(2) 1 calc R U P B 2
C66A C 0.7467(4) 0.04735(14) 0.46705(17) 0.0294(5) Uani 0.901(2) 1 d D U P B 1
H66A H 0.787869 -0.018986 0.484131 0.035 Uiso 0.901(2) 1 calc R U P B 1
C66B C 0.666(4) 0.0786(13) 0.5086(18) 0.033(5) Uani 0.099(2) 1 d D U P B 2
H66B H 0.647352 0.033506 0.563483 0.039 Uiso 0.099(2) 1 calc R U P B 2
C57 C 0.5653(2) 0.59767(10) 0.04782(10) 0.0233(3) Uani 1 1 d . U . . .
H57A H 0.434762 0.593368 0.036179 0.028 Uiso 1 1 calc R U . . .
H57B H 0.657570 0.550762 0.023262 0.028 Uiso 1 1 calc R U . . .
C58 C 0.5956(2) 0.69575(10) 0.00203(10) 0.0239(3) Uani 1 1 d . U . . .
H58A H 0.730382 0.697391 0.008568 0.029 Uiso 1 1 calc R U . . .
H58B H 0.568720 0.711416 -0.063857 0.029 Uiso 1 1 calc R U . . .
C59 C 0.2872(2) 0.80335(11) -0.00293(11) 0.0277(3) Uani 1 1 d . U . . .
H59A H 0.225291 0.751516 -0.002899 0.033 Uiso 1 1 calc R U . . .
H59B H 0.306521 0.837304 -0.067050 0.033 Uiso 1 1 calc R U . . .
C60 C 0.1604(2) 0.86963(12) 0.04633(12) 0.0313(4) Uani 1 1 d . U . . .
H60A H 0.036622 0.895761 0.014816 0.038 Uiso 1 1 calc R U . . .
H60B H 0.135401 0.834419 0.109300 0.038 Uiso 1 1 calc R U . . .
C61 C 0.4264(2) 0.90732(11) 0.09293(11) 0.0296(3) Uani 1 1 d . U . . .
H61A H 0.406957 0.872029 0.156555 0.036 Uiso 1 1 calc R U . . .
H61B H 0.486065 0.959359 0.094688 0.036 Uiso 1 1 calc R U . . .
C62 C 0.5585(2) 0.84305(11) 0.04381(11) 0.0270(3) Uani 1 1 d . U . . .
H62A H 0.581779 0.878276 -0.019379 0.032 Uiso 1 1 calc R U . . .
H62B H 0.682452 0.818339 0.075334 0.032 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
S1A C13 1.7067(16) . ?
S1A C16A 1.712(4) . ?
S1B C13 1.692(3) . ?
S1B C16B 1.707(9) . ?
O1 N1 1.2393(16) . ?
O2 N1 1.2452(16) . ?
O3 C10 1.4285(19) . ?
O3 C11 1.4263(18) . ?
N1 C2 1.4410(19) . ?
N2 H2 0.856(9) . ?
N2 C1 1.3475(19) . ?
N2 C7 1.4531(19) . ?
N3 C8 1.456(2) . ?
N3 C9 1.4645(19) . ?
N3 C12 1.4615(19) . ?
C4 C3 1.385(2) . ?
C4 C5 1.412(2) . ?
C4 C13 1.471(2) . ?
C3 H3 0.9500 . ?
C3 C2 1.398(2) . ?
C2 C1 1.424(2) . ?
C1 C6 1.424(2) . ?
C6 H6 0.9500 . ?
C6 C5 1.368(2) . ?
C5 H5 0.9500 . ?
C13 C14A 1.373(6) . ?
C13 C14B 1.390(10) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.420(8) . ?
C14B H14B 0.9500 . ?
C14B C15B 1.420(14) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.371(5) . ?
C15B H15B 0.9500 . ?
C15B C16B 1.365(11) . ?
C16A H16A 0.9500 . ?
C16B H16B 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.526(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.511(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.502(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
S51A C63 1.7167(16) . ?
S51A C66A 1.719(2) . ?
S51B C63 1.603(8) . ?
S51B C66B 1.722(17) . ?
O51 N51 1.2383(17) . ?
O52 N51 1.2457(17) . ?
O53 C60 1.432(2) . ?
O53 C61 1.423(2) . ?
N51 C52 1.4377(19) . ?
N52 H52 0.855(9) . ?
N52 C51 1.3501(19) . ?
N52 C57 1.4508(19) . ?
N53 C58 1.4637(19) . ?
N53 C59 1.462(2) . ?
N53 C62 1.4639(19) . ?
C54 C53 1.378(2) . ?
C54 C55 1.411(2) . ?
C54 C63 1.473(2) . ?
C53 H53 0.9500 . ?
C53 C52 1.401(2) . ?
C52 C51 1.422(2) . ?
C51 C56 1.421(2) . ?
C56 H56 0.9500 . ?
C56 C55 1.368(2) . ?
C55 H55 0.9500 . ?
C63 C64A 1.347(5) . ?
C63 C64B 1.323(17) . ?
C64A H64A 0.9500 . ?
C64A C65A 1.438(6) . ?
C64B H64B 0.9500 . ?
C64B C65B 1.450(17) . ?
C65A H65A 0.9500 . ?
C65A C66A 1.357(3) . ?
C65B H65B 0.9500 . ?
C65B C66B 1.340(17) . ?
C66A H66A 0.9500 . ?
C66B H66B 0.9500 . ?
C57 H57A 0.9900 . ?
C57 H57B 0.9900 . ?
C57 C58 1.522(2) . ?
C58 H58A 0.9900 . ?
C58 H58B 0.9900 . ?
C59 H59A 0.9900 . ?
C59 H59B 0.9900 . ?
C59 C60 1.516(2) . ?
C60 H60A 0.9900 . ?
C60 H60B 0.9900 . ?
C61 H61A 0.9900 . ?
C61 H61B 0.9900 . ?
C61 C62 1.512(2) . ?
C62 H62A 0.9900 . ?
C62 H62B 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
C13 S1A C16A 92.5(2) . . ?
C13 S1B C16B 93.4(5) . . ?
C11 O3 C10 109.65(12) . . ?
O1 N1 O2 121.34(12) . . ?
O1 N1 C2 119.05(12) . . ?
O2 N1 C2 119.62(12) . . ?
C1 N2 H2 117.0(13) . . ?
C1 N2 C7 124.45(13) . . ?
C7 N2 H2 117.2(13) . . ?
C8 N3 C9 112.39(12) . . ?
C8 N3 C12 112.09(12) . . ?
C12 N3 C9 108.84(12) . . ?
C3 C4 C5 117.18(13) . . ?
C3 C4 C13 121.39(13) . . ?
C5 C4 C13 121.38(13) . . ?
C4 C3 H3 119.5 . . ?
C4 C3 C2 121.01(13) . . ?
C2 C3 H3 119.5 . . ?
C3 C2 N1 116.51(13) . . ?
C3 C2 C1 122.54(13) . . ?
C1 C2 N1 120.90(13) . . ?
N2 C1 C2 124.19(13) . . ?
N2 C1 C6 120.89(13) . . ?
C6 C1 C2 114.89(13) . . ?
C1 C6 H6 119.0 . . ?
C5 C6 C1 122.01(14) . . ?
C5 C6 H6 119.0 . . ?
C4 C5 H5 118.8 . . ?
C6 C5 C4 122.35(14) . . ?
C6 C5 H5 118.8 . . ?
C4 C13 S1A 121.36(12) . . ?
C4 C13 S1B 124.90(18) . . ?
C14A C13 S1A 111.0(4) . . ?
C14A C13 C4 127.4(4) . . ?
C14B C13 S1B 110.9(6) . . ?
C14B C13 C4 124.1(6) . . ?
C13 C14A H14A 123.5 . . ?
C13 C14A C15A 112.9(6) . . ?
C15A C14A H14A 123.5 . . ?
C13 C14B H14B 124.1 . . ?
C13 C14B C15B 111.8(11) . . ?
C15B C14B H14B 124.1 . . ?
C14A C15A H15A 124.0 . . ?
C16A C15A C14A 112.1(5) . . ?
C16A C15A H15A 124.0 . . ?
C14B C15B H15B 123.4 . . ?
C16B C15B C14B 113.1(12) . . ?
C16B C15B H15B 123.4 . . ?
S1A C16A H16A 124.3 . . ?
C15A C16A S1A 111.5(4) . . ?
C15A C16A H16A 124.3 . . ?
S1B C16B H16B 124.6 . . ?
C15B C16B S1B 110.7(10) . . ?
C15B C16B H16B 124.6 . . ?
N2 C7 H7A 110.0 . . ?
N2 C7 H7B 110.0 . . ?
N2 C7 C8 108.33(13) . . ?
H7A C7 H7B 108.4 . . ?
C8 C7 H7A 110.0 . . ?
C8 C7 H7B 110.0 . . ?
N3 C8 C7 111.59(12) . . ?
N3 C8 H8A 109.3 . . ?
N3 C8 H8B 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
N3 C9 H9A 109.6 . . ?
N3 C9 H9B 109.6 . . ?
N3 C9 C10 110.20(13) . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
O3 C10 C9 111.50(13) . . ?
O3 C10 H10A 109.3 . . ?
O3 C10 H10B 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
O3 C11 H11A 109.4 . . ?
O3 C11 H11B 109.4 . . ?
O3 C11 C12 111.25(13) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
N3 C12 C11 108.38(12) . . ?
N3 C12 H12A 110.0 . . ?
N3 C12 H12B 110.0 . . ?
C11 C12 H12A 110.0 . . ?
C11 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
C63 S51A C66A 92.31(10) . . ?
C63 S51B C66B 91.2(9) . . ?
C61 O53 C60 109.41(12) . . ?
O51 N51 O52 121.15(12) . . ?
O51 N51 C52 119.36(12) . . ?
O52 N51 C52 119.49(12) . . ?
C51 N52 H52 117.7(13) . . ?
C51 N52 C57 125.18(13) . . ?
C57 N52 H52 115.9(13) . . ?
C58 N53 C62 112.92(12) . . ?
C59 N53 C58 112.32(12) . . ?
C59 N53 C62 109.01(12) . . ?
C53 C54 C55 117.43(13) . . ?
C53 C54 C63 121.59(13) . . ?
C55 C54 C63 120.92(13) . . ?
C54 C53 H53 119.3 . . ?
C54 C53 C52 121.43(14) . . ?
C52 C53 H53 119.3 . . ?
C53 C52 N51 116.77(13) . . ?
C53 C52 C51 121.90(13) . . ?
C51 C52 N51 121.33(13) . . ?
N52 C51 C52 124.26(13) . . ?
N52 C51 C56 120.61(13) . . ?
C56 C51 C52 115.11(13) . . ?
C51 C56 H56 118.8 . . ?
C55 C56 C51 122.31(14) . . ?
C55 C56 H56 118.8 . . ?
C54 C55 H55 119.1 . . ?
C56 C55 C54 121.80(14) . . ?
C56 C55 H55 119.1 . . ?
C54 C63 S51A 122.23(11) . . ?
C54 C63 S51B 124.5(5) . . ?
C64A C63 S51A 110.4(3) . . ?
C64A C63 C54 127.3(3) . . ?
C64B C63 S51B 115.7(10) . . ?
C64B C63 C54 119.8(9) . . ?
C63 C64A H64A 122.8 . . ?
C63 C64A C65A 114.5(4) . . ?
C65A C64A H64A 122.8 . . ?
C63 C64B H64B 124.4 . . ?
C63 C64B C65B 111.3(15) . . ?
C65B C64B H64B 124.4 . . ?
C64A C65A H65A 124.6 . . ?
C66A C65A C64A 110.8(3) . . ?
C66A C65A H65A 124.6 . . ?
C64B C65B H65B 125.4 . . ?
C66B C65B C64B 109.2(16) . . ?
C66B C65B H65B 125.4 . . ?
S51A C66A H66A 124.0 . . ?
C65A C66A S51A 112.01(16) . . ?
C65A C66A H66A 124.0 . . ?
S51B C66B H66B 124.0 . . ?
C65B C66B S51B 112.0(15) . . ?
C65B C66B H66B 124.0 . . ?
N52 C57 H57A 110.1 . . ?
N52 C57 H57B 110.1 . . ?
N52 C57 C58 107.80(12) . . ?
H57A C57 H57B 108.5 . . ?
C58 C57 H57A 110.1 . . ?
C58 C57 H57B 110.1 . . ?
N53 C58 C57 111.02(12) . . ?
N53 C58 H58A 109.4 . . ?
N53 C58 H58B 109.4 . . ?
C57 C58 H58A 109.4 . . ?
C57 C58 H58B 109.4 . . ?
H58A C58 H58B 108.0 . . ?
N53 C59 H59A 109.7 . . ?
N53 C59 H59B 109.7 . . ?
N53 C59 C60 109.63(12) . . ?
H59A C59 H59B 108.2 . . ?
C60 C59 H59A 109.7 . . ?
C60 C59 H59B 109.7 . . ?
O53 C60 C59 111.48(14) . . ?
O53 C60 H60A 109.3 . . ?
O53 C60 H60B 109.3 . . ?
C59 C60 H60A 109.3 . . ?
C59 C60 H60B 109.3 . . ?
H60A C60 H60B 108.0 . . ?
O53 C61 H61A 109.3 . . ?
O53 C61 H61B 109.3 . . ?
O53 C61 C62 111.58(13) . . ?
H61A C61 H61B 108.0 . . ?
C62 C61 H61A 109.3 . . ?
C62 C61 H61B 109.3 . . ?
N53 C62 C61 109.17(13) . . ?
N53 C62 H62A 109.8 . . ?
N53 C62 H62B 109.8 . . ?
C61 C62 H62A 109.8 . . ?
C61 C62 H62B 109.8 . . ?
H62A C62 H62B 108.3 . . ?

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
_geom_hbond_publ_flag
N2 H2 O2 0.856(9) 1.995(16) 2.6365(17) 130.9(16) . yes
N52 H52 O52 0.855(9) 1.997(16) 2.6238(16) 129.4(16) . yes

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
S1A C13 C14A C15A 1.8(8) . . . . ?
S1B C13 C14B C15B 1.2(15) . . . . ?
O1 N1 C2 C3 -11.91(19) . . . . ?
O1 N1 C2 C1 165.66(13) . . . . ?
O2 N1 C2 C3 168.31(13) . . . . ?
O2 N1 C2 C1 -14.1(2) . . . . ?
O3 C11 C12 N3 -61.74(16) . . . . ?
N1 C2 C1 N2 -0.7(2) . . . . ?
N1 C2 C1 C6 -178.72(13) . . . . ?
N2 C1 C6 C5 -177.40(14) . . . . ?
N2 C7 C8 N3 47.32(17) . . . . ?
N3 C9 C10 O3 56.56(17) . . . . ?
C4 C3 C2 N1 178.19(13) . . . . ?
C4 C3 C2 C1 0.7(2) . . . . ?
C4 C13 C14A C15A 176.8(4) . . . . ?
C4 C13 C14B C15B -175.6(10) . . . . ?
C3 C4 C5 C6 -1.3(2) . . . . ?
C3 C4 C13 S1A 147.22(13) . . . . ?
C3 C4 C13 S1B -31.6(3) . . . . ?
C3 C4 C13 C14A -27.3(5) . . . . ?
C3 C4 C13 C14B 144.8(8) . . . . ?
C3 C2 C1 N2 176.71(14) . . . . ?
C3 C2 C1 C6 -1.3(2) . . . . ?
C2 C1 C6 C5 0.7(2) . . . . ?
C1 N2 C7 C8 176.63(14) . . . . ?
C1 C6 C5 C4 0.6(2) . . . . ?
C5 C4 C3 C2 0.6(2) . . . . ?
C5 C4 C13 S1A -30.2(2) . . . . ?
C5 C4 C13 S1B 151.0(2) . . . . ?
C5 C4 C13 C14A 155.3(5) . . . . ?
C5 C4 C13 C14B -32.6(8) . . . . ?
C13 S1A C16A C15A 0.1(5) . . . . ?
C13 S1B C16B C15B 1.7(11) . . . . ?
C13 C4 C3 C2 -176.87(13) . . . . ?
C13 C4 C5 C6 176.25(14) . . . . ?
C13 C14A C15A C16A -1.7(9) . . . . ?
C13 C14B C15B C16B 0.0(19) . . . . ?
C14A C15A C16A S1A 0.8(8) . . . . ?
C14B C15B C16B S1B -1.2(18) . . . . ?
C16A S1A C13 C4 -176.4(3) . . . . ?
C16A S1A C13 C14A -1.1(5) . . . . ?
C16B S1B C13 C4 175.1(6) . . . . ?
C16B S1B C13 C14B -1.6(9) . . . . ?
C7 N2 C1 C2 179.47(14) . . . . ?
C7 N2 C1 C6 -2.6(2) . . . . ?
C8 N3 C9 C10 177.43(13) . . . . ?
C8 N3 C12 C11 -175.24(12) . . . . ?
C9 N3 C8 C7 -171.48(13) . . . . ?
C9 N3 C12 C11 59.80(15) . . . . ?
C10 O3 C11 C12 59.69(16) . . . . ?
C11 O3 C10 C9 -56.65(17) . . . . ?
C12 N3 C8 C7 65.55(16) . . . . ?
C12 N3 C9 C10 -57.80(16) . . . . ?
S51A C63 C64A C65A -1.1(7) . . . . ?
S51B C63 C64B C65B 3(3) . . . . ?
O51 N51 C52 C53 6.6(2) . . . . ?
O51 N51 C52 C51 -172.60(14) . . . . ?
O52 N51 C52 C53 -173.10(13) . . . . ?
O52 N51 C52 C51 7.7(2) . . . . ?
O53 C61 C62 N53 -59.85(16) . . . . ?
N51 C52 C51 N52 0.5(2) . . . . ?
N51 C52 C51 C56 178.98(13) . . . . ?
N52 C51 C56 C55 179.07(14) . . . . ?
N52 C57 C58 N53 -55.19(16) . . . . ?
N53 C59 C60 O53 58.28(17) . . . . ?
C54 C53 C52 N51 -179.83(13) . . . . ?
C54 C53 C52 C51 -0.7(2) . . . . ?
C54 C63 C64A C65A 175.1(3) . . . . ?
C54 C63 C64B C65B -174.1(18) . . . . ?
C53 C54 C55 C56 -0.7(2) . . . . ?
C53 C54 C63 S51A -138.55(13) . . . . ?
C53 C54 C63 S51B 47.1(8) . . . . ?
C53 C54 C63 C64A 45.7(5) . . . . ?
C53 C54 C63 C64B -136.0(19) . . . . ?
C53 C52 C51 N52 -178.60(14) . . . . ?
C53 C52 C51 C56 -0.1(2) . . . . ?
C52 C51 C56 C55 0.5(2) . . . . ?
C51 N52 C57 C58 -166.30(14) . . . . ?
C51 C56 C55 C54 -0.2(2) . . . . ?
C55 C54 C53 C52 1.1(2) . . . . ?
C55 C54 C63 S51A 44.34(19) . . . . ?
C55 C54 C63 S51B -130.0(8) . . . . ?
C55 C54 C63 C64A -131.4(5) . . . . ?
C55 C54 C63 C64B 46.9(19) . . . . ?
C63 S51A C66A C65A -0.4(2) . . . . ?
C63 S51B C66B C65B -6(3) . . . . ?
C63 C54 C53 C52 -176.15(14) . . . . ?
C63 C54 C55 C56 176.57(14) . . . . ?
C63 C64A C65A C66A 0.9(7) . . . . ?
C63 C64B C65B C66B -7(4) . . . . ?
C64A C65A C66A S51A -0.2(5) . . . . ?
C64B C65B C66B S51B 9(4) . . . . ?
C66A S51A C63 C54 -175.58(15) . . . . ?
C66A S51A C63 C64A 0.8(4) . . . . ?
C66B S51B C63 C54 178.6(13) . . . . ?
C66B S51B C63 C64B 2(2) . . . . ?
C57 N52 C51 C52 179.89(14) . . . . ?
C57 N52 C51 C56 1.5(2) . . . . ?
C58 N53 C59 C60 176.01(13) . . . . ?
C58 N53 C62 C61 -175.81(12) . . . . ?
C59 N53 C58 C57 -89.75(15) . . . . ?
C59 N53 C62 C61 58.61(15) . . . . ?
C60 O53 C61 C62 58.74(17) . . . . ?
C61 O53 C60 C59 -57.82(17) . . . . ?
C62 N53 C58 C57 146.48(13) . . . . ?
C62 N53 C59 C60 -58.06(16) . . . . ?

_olex2_date_sample_data_collection 2018-06-08
_olex2_date_sample_submission    2018-05-16
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id AKE-019
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.818
_oxdiff_exptl_absorpt_empirical_full_min 0.696
####################################################################### 
# 
# 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_18
_database_code_depnum_ccdc_archive 'CCDC 2110087'
loop_
_audit_author_name
_audit_author_address
'Graham Tizzard'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2021-09-15 deposited with the CCDC.	2022-04-25 downloaded from the CCDC.
;

#2019ncs0241z

_audit_creation_date             2021-09-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
?
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H21 N3 O4'
_chemical_formula_sum            'C17 H21 N3 O4'
_chemical_formula_weight         331.37
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H21 N3 O4 '
_chemical_oxdiff_usercomment     AKE-020
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   7.10820(10)
_cell_length_b                   14.5273(2)
_cell_length_c                   31.5780(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3260.84(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7713
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.9190
_cell_measurement_theta_min      3.3420
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.794
_exptl_absorpt_coefficient_mu    0.804
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61539
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.47a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       lath
_exptl_crystal_F_000             1408
_exptl_crystal_recrystallization_method 
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            30549
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.367
_diffrn_reflns_theta_min         2.799
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00  94.00   0.50    0.50    --    5.00  20.00-150.00  356
  2  ω   -179.00  -1.00   0.50    2.00    --  -90.00  58.00  28.40  356
  3  ω   -179.00  -1.00   0.50    2.00    --  -90.00  59.00-109.15  356
  4  ω   -179.00  -1.00   0.50    2.00    --  -90.00  30.00 150.00  356
  5  ω   -179.00 -12.00   0.50    2.00    --  -90.00  58.00-142.44  334
  6  ω   -129.00 -21.00   0.50    2.00    --  -90.00  57.00 -84.21  216
  7  ω   -178.00  -3.00   0.50    2.00    --  -90.00  59.00 -45.22  350
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_details 'Rigaku, AFC11 quarter χ goniometer'
_diffrn_measurement_device_type  
'Rigaku 007HF equipped with Varimax confocal mirrors and an AFC11 goniometer and HyPix 6000 detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0173646000
_diffrn_orient_matrix_UB_12      0.1055128000
_diffrn_orient_matrix_UB_13      -0.0028842000
_diffrn_orient_matrix_UB_21      -0.0096821000
_diffrn_orient_matrix_UB_22      0.0059834000
_diffrn_orient_matrix_UB_23      0.0486607000
_diffrn_orient_matrix_UB_31      0.2158099000
_diffrn_orient_matrix_UB_32      0.0088190000
_diffrn_orient_matrix_UB_33      0.0019704000
_diffrn_radiation_collimation    'Varimax focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Rotating anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'Rigaku 007 HF'
_diffrn_source_voltage           40.0
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                5507
_reflns_number_total             6152
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 
;
 Flack x determined using 2116 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     441
_refine_ls_number_reflns         6152
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0533
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0674P)²+0.9373P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1309
_refine_special_details          
'Hydrogen atoms H1 and H101 bonded to N1 and N101 were located in the difference map and refined with a riding model.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N52-H52 \\sim N2-H2
 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C58(H58A,H58B), C8(H8A,H8B), C12(H12A,H12B), C7(H7A,H7B), C59(H59A,H59B),
 C9(H9A,H9B), C62(H62A,H62B), C57(H57A,H57B), C60(H60A,H60B), C61(H61A,H61B),
 C10(H10A,H10B), C11(H11A,H11B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C53(H53), C64(H64), C5(H5), C56(H56), C6(H6), C55(H55), C14(H14),
 C65(H65), C15(H15)
3.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C67(H67A,H67B,H67C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O54 O 0.3174(4) 0.33489(16) 0.61210(7) 0.0313(5) Uani 1 1 d . . . . .
O4 O 0.1895(3) 0.87953(15) 0.88289(7) 0.0301(5) Uani 1 1 d . . . . .
O51 O 0.0862(4) 0.44386(16) 0.82627(8) 0.0369(6) Uani 1 1 d . . . . .
O1 O 0.4034(4) 0.76998(16) 0.66845(7) 0.0363(6) Uani 1 1 d . . . . .
O52 O 0.1158(4) 0.55043(15) 0.77866(8) 0.0377(6) Uani 1 1 d . . . . .
O3 O 0.1278(4) 0.98391(18) 0.53371(8) 0.0428(6) Uani 1 1 d . . . . .
O2 O 0.3872(4) 0.66371(15) 0.71648(8) 0.0385(6) Uani 1 1 d . . . . .
O53 O 0.3454(4) 0.2329(2) 0.96465(8) 0.0445(7) Uani 1 1 d . . . . .
N51 N 0.1164(4) 0.46713(18) 0.78919(9) 0.0299(6) Uani 1 1 d . . . . .
N53 N 0.1299(4) 0.20869(19) 0.88943(9) 0.0303(6) Uani 1 1 d . . . . .
N1 N 0.3815(4) 0.74631(19) 0.70583(9) 0.0295(6) Uani 1 1 d . . . . .
N52 N 0.0835(4) 0.26976(19) 0.80473(9) 0.0288(6) Uani 1 1 d D . . . .
H52 H 0.085(6) 0.305(3) 0.8267(11) 0.035 Uiso 1 1 d D U . . .
N3 N 0.3632(4) 1.00262(19) 0.60632(9) 0.0308(6) Uani 1 1 d . . . . .
N2 N 0.4239(4) 0.94291(19) 0.69042(9) 0.0297(6) Uani 1 1 d D . . . .
H2 H 0.406(6) 0.908(3) 0.6691(11) 0.036 Uiso 1 1 d D U . . .
C4 C 0.2600(5) 0.8447(2) 0.81039(11) 0.0267(7) Uani 1 1 d . . . . .
C3 C 0.2939(5) 0.7837(2) 0.77745(11) 0.0271(7) Uani 1 1 d . . . . .
H3 H 0.280728 0.719475 0.782152 0.033 Uiso 1 1 calc R U . . .
C1 C 0.3694(5) 0.9104(2) 0.72826(10) 0.0257(7) Uani 1 1 d . . . . .
C52 C 0.1542(5) 0.3994(2) 0.75732(10) 0.0257(7) Uani 1 1 d . . . . .
C53 C 0.2073(5) 0.4304(2) 0.71748(11) 0.0282(7) Uani 1 1 d . . . . .
H53 H 0.217364 0.494710 0.712607 0.034 Uiso 1 1 calc R U . . .
C51 C 0.1358(5) 0.3033(2) 0.76692(10) 0.0265(7) Uani 1 1 d . . . . .
C13 C 0.2046(5) 0.8128(2) 0.85186(10) 0.0272(7) Uani 1 1 d . . . . .
C64 C 0.3434(5) 0.4854(2) 0.62601(11) 0.0311(8) Uani 1 1 d . . . . .
H64 H 0.344809 0.542837 0.640371 0.037 Uiso 1 1 calc R U . . .
C54 C 0.2457(5) 0.3703(2) 0.68480(11) 0.0270(7) Uani 1 1 d . . . . .
C66 C 0.3668(5) 0.3785(3) 0.57537(11) 0.0330(8) Uani 1 1 d . . . . .
C5 C 0.2840(5) 0.9401(2) 0.80176(11) 0.0274(7) Uani 1 1 d . . . . .
H5 H 0.262172 0.983511 0.823732 0.033 Uiso 1 1 calc R U . . .
C2 C 0.3468(5) 0.8152(2) 0.73773(11) 0.0267(7) Uani 1 1 d . . . . .
C56 C 0.1718(5) 0.2433(2) 0.73224(11) 0.0279(7) Uani 1 1 d . . . . .
H56 H 0.159121 0.178816 0.736372 0.033 Uiso 1 1 calc R U . . .
C63 C 0.3018(5) 0.4013(2) 0.64325(11) 0.0282(7) Uani 1 1 d . . . . .
C6 C 0.3374(5) 0.9709(2) 0.76283(11) 0.0288(7) Uani 1 1 d . . . . .
H6 H 0.353868 1.035149 0.758658 0.035 Uiso 1 1 calc R U . . .
C55 C 0.2237(5) 0.2747(2) 0.69340(11) 0.0290(7) Uani 1 1 d . . . . .
H55 H 0.245974 0.231623 0.671339 0.035 Uiso 1 1 calc R U . . .
C16 C 0.1405(5) 0.8360(2) 0.91969(11) 0.0317(8) Uani 1 1 d . . . . .
C58 C 0.0123(5) 0.1587(2) 0.85959(12) 0.0330(8) Uani 1 1 d . . . . .
H58A H -0.119061 0.180622 0.862141 0.040 Uiso 1 1 calc R U . . .
H58B H 0.014315 0.092398 0.866782 0.040 Uiso 1 1 calc R U . . .
C8 C 0.4905(5) 1.0512(2) 0.63453(11) 0.0339(8) Uani 1 1 d . . . . .
H8A H 0.492203 1.117292 0.626887 0.041 Uiso 1 1 calc R U . . .
H8B H 0.619432 1.026754 0.630800 0.041 Uiso 1 1 calc R U . . .
C12 C 0.1818(5) 1.0506(2) 0.60283(12) 0.0349(8) Uani 1 1 d . . . . .
H12A H 0.201438 1.112762 0.590801 0.042 Uiso 1 1 calc R U . . .
H12B H 0.125057 1.057521 0.631282 0.042 Uiso 1 1 calc R U . . .
C7 C 0.4331(6) 1.0413(2) 0.68049(12) 0.0335(8) Uani 1 1 d . . . . .
H7A H 0.526276 1.072038 0.699016 0.040 Uiso 1 1 calc R U . . .
H7B H 0.308861 1.070310 0.685187 0.040 Uiso 1 1 calc R U . . .
C59 C 0.3123(5) 0.1642(2) 0.89522(12) 0.0348(8) Uani 1 1 d . . . . .
H59A H 0.376024 0.157729 0.867501 0.042 Uiso 1 1 calc R U . . .
H59B H 0.294148 0.101858 0.907244 0.042 Uiso 1 1 calc R U . . .
C9 C 0.4412(5) 0.9911(3) 0.56399(11) 0.0353(8) Uani 1 1 d . . . . .
H9A H 0.561996 0.957400 0.565713 0.042 Uiso 1 1 calc R U . . .
H9B H 0.466071 1.052271 0.551310 0.042 Uiso 1 1 calc R U . . .
C14 C 0.1632(5) 0.7292(2) 0.86891(11) 0.0308(8) Uani 1 1 d . . . . .
H14 H 0.160518 0.671949 0.854424 0.037 Uiso 1 1 calc R U . . .
C62 C 0.0398(5) 0.2193(3) 0.93061(12) 0.0365(8) Uani 1 1 d . . . . .
H62A H 0.015758 0.158036 0.943192 0.044 Uiso 1 1 calc R U . . .
H62B H -0.082404 0.251202 0.927208 0.044 Uiso 1 1 calc R U . . .
C57 C 0.0782(6) 0.1713(2) 0.81425(11) 0.0348(8) Uani 1 1 d . . . . .
H57A H 0.204953 0.144188 0.810647 0.042 Uiso 1 1 calc R U . . .
H57B H -0.009191 0.139675 0.794630 0.042 Uiso 1 1 calc R U . . .
C17 C 0.1163(6) 0.8960(3) 0.95713(11) 0.0376(8) Uani 1 1 d . . . . .
H17A H 0.234703 0.928081 0.963062 0.056 Uiso 1 1 calc R U . . .
H17B H 0.081095 0.858421 0.981656 0.056 Uiso 1 1 calc R U . . .
H17C H 0.017161 0.941239 0.951496 0.056 Uiso 1 1 calc R U . . .
C65 C 0.3841(5) 0.4701(2) 0.58234(11) 0.0340(8) Uani 1 1 d . . . . .
H65 H 0.416980 0.515501 0.562011 0.041 Uiso 1 1 calc R U . . .
C15 C 0.1246(5) 0.7440(2) 0.91257(11) 0.0330(8) Uani 1 1 d . . . . .
H15 H 0.093611 0.698288 0.932907 0.040 Uiso 1 1 calc R U . . .
C60 C 0.4327(5) 0.2211(3) 0.92472(12) 0.0375(8) Uani 1 1 d . . . . .
H60A H 0.555746 0.190372 0.928642 0.045 Uiso 1 1 calc R U . . .
H60B H 0.455830 0.282157 0.911815 0.045 Uiso 1 1 calc R U . . .
C61 C 0.1663(5) 0.2747(3) 0.95955(13) 0.0429(9) Uani 1 1 d . . . . .
H61A H 0.182726 0.337243 0.947662 0.051 Uiso 1 1 calc R U . . .
H61B H 0.105406 0.280894 0.987603 0.051 Uiso 1 1 calc R U . . .
C10 C 0.3048(6) 0.9383(3) 0.53640(12) 0.0402(9) Uani 1 1 d . . . . .
H10A H 0.358450 0.931609 0.507639 0.048 Uiso 1 1 calc R U . . .
H10B H 0.286305 0.875914 0.548289 0.048 Uiso 1 1 calc R U . . .
C11 C 0.0516(6) 0.9964(3) 0.57475(12) 0.0394(9) Uani 1 1 d . . . . .
H11A H 0.027586 0.935512 0.587718 0.047 Uiso 1 1 calc R U . . .
H11B H -0.070160 1.029125 0.572483 0.047 Uiso 1 1 calc R U . . .
C67 C 0.3903(6) 0.3192(3) 0.53747(12) 0.0421(9) Uani 1 1 d . . . . .
H67A H 0.485922 0.272215 0.543188 0.063 Uiso 1 1 calc R U . . .
H67B H 0.429978 0.356979 0.513370 0.063 Uiso 1 1 calc R U . . .
H67C H 0.270361 0.289179 0.530820 0.063 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
O54 C66 1.367(4) . ?
O54 C63 1.383(4) . ?
O4 C13 1.383(4) . ?
O4 C16 1.368(4) . ?
O51 N51 1.237(4) . ?
O1 N1 1.239(4) . ?
O52 N51 1.255(4) . ?
O3 C10 1.424(5) . ?
O3 C11 1.416(5) . ?
O2 N1 1.247(4) . ?
O53 C60 1.416(5) . ?
O53 C61 1.420(5) . ?
N51 C52 1.433(4) . ?
N53 C58 1.454(5) . ?
N53 C59 1.460(5) . ?
N53 C62 1.458(5) . ?
N1 C2 1.442(4) . ?
N52 H52 0.87(3) . ?
N52 C51 1.342(4) . ?
N52 C57 1.462(4) . ?
N3 C8 1.453(5) . ?
N3 C12 1.470(5) . ?
N3 C9 1.457(5) . ?
N2 H2 0.86(3) . ?
N2 C1 1.342(4) . ?
N2 C7 1.465(4) . ?
C4 C3 1.387(5) . ?
C4 C13 1.444(5) . ?
C4 C5 1.424(5) . ?
C3 H3 0.9500 . ?
C3 C2 1.387(5) . ?
C1 C2 1.423(5) . ?
C1 C6 1.420(5) . ?
C52 C53 1.388(5) . ?
C52 C51 1.435(4) . ?
C53 H53 0.9500 . ?
C53 C54 1.379(5) . ?
C51 C56 1.423(5) . ?
C13 C14 1.360(5) . ?
C64 H64 0.9500 . ?
C64 C63 1.369(5) . ?
C64 C65 1.426(5) . ?
C54 C63 1.443(5) . ?
C54 C55 1.423(4) . ?
C66 C65 1.354(5) . ?
C66 C67 1.484(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.362(5) . ?
C56 H56 0.9500 . ?
C56 C55 1.360(5) . ?
C6 H6 0.9500 . ?
C55 H55 0.9500 . ?
C16 C17 1.478(5) . ?
C16 C15 1.360(5) . ?
C58 H58A 0.9900 . ?
C58 H58B 0.9900 . ?
C58 C57 1.517(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.514(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.504(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C59 H59A 0.9900 . ?
C59 H59B 0.9900 . ?
C59 C60 1.511(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.513(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.422(5) . ?
C62 H62A 0.9900 . ?
C62 H62B 0.9900 . ?
C62 C61 1.513(6) . ?
C57 H57A 0.9900 . ?
C57 H57B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C65 H65 0.9500 . ?
C15 H15 0.9500 . ?
C60 H60A 0.9900 . ?
C60 H60B 0.9900 . ?
C61 H61A 0.9900 . ?
C61 H61B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C67 H67A 0.9800 . ?
C67 H67B 0.9800 . ?
C67 H67C 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
C66 O54 C63 107.5(3) . . ?
C16 O4 C13 107.3(3) . . ?
C11 O3 C10 110.0(3) . . ?
C60 O53 C61 110.1(3) . . ?
O51 N51 O52 120.9(3) . . ?
O51 N51 C52 120.6(3) . . ?
O52 N51 C52 118.5(3) . . ?
C58 N53 C59 111.7(3) . . ?
C58 N53 C62 112.2(3) . . ?
C62 N53 C59 109.0(3) . . ?
O1 N1 O2 121.3(3) . . ?
O1 N1 C2 119.6(3) . . ?
O2 N1 C2 119.1(3) . . ?
C51 N52 H52 120(3) . . ?
C51 N52 C57 123.0(3) . . ?
C57 N52 H52 115(3) . . ?
C8 N3 C12 111.2(3) . . ?
C8 N3 C9 112.4(3) . . ?
C9 N3 C12 108.6(3) . . ?
C1 N2 H2 117(3) . . ?
C1 N2 C7 123.2(3) . . ?
C7 N2 H2 115(3) . . ?
C3 C4 C13 121.5(3) . . ?
C3 C4 C5 117.2(3) . . ?
C5 C4 C13 121.2(3) . . ?
C4 C3 H3 119.5 . . ?
C4 C3 C2 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
N2 C1 C2 124.2(3) . . ?
N2 C1 C6 120.9(3) . . ?
C6 C1 C2 114.9(3) . . ?
N51 C52 C51 120.2(3) . . ?
C53 C52 N51 117.7(3) . . ?
C53 C52 C51 122.1(3) . . ?
C52 C53 H53 119.1 . . ?
C54 C53 C52 121.8(3) . . ?
C54 C53 H53 119.1 . . ?
N52 C51 C52 124.5(3) . . ?
N52 C51 C56 120.8(3) . . ?
C56 C51 C52 114.6(3) . . ?
O4 C13 C4 116.1(3) . . ?
C14 C13 O4 109.2(3) . . ?
C14 C13 C4 134.8(3) . . ?
C63 C64 H64 126.6 . . ?
C63 C64 C65 106.8(3) . . ?
C65 C64 H64 126.6 . . ?
C53 C54 C63 122.5(3) . . ?
C53 C54 C55 116.9(3) . . ?
C55 C54 C63 120.6(3) . . ?
O54 C66 C67 116.4(3) . . ?
C65 C66 O54 109.9(3) . . ?
C65 C66 C67 133.7(3) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 C4 121.7(3) . . ?
C6 C5 H5 119.1 . . ?
C3 C2 N1 116.7(3) . . ?
C3 C2 C1 122.8(3) . . ?
C1 C2 N1 120.6(3) . . ?
C51 C56 H56 118.7 . . ?
C55 C56 C51 122.5(3) . . ?
C55 C56 H56 118.7 . . ?
O54 C63 C54 116.8(3) . . ?
C64 C63 O54 108.8(3) . . ?
C64 C63 C54 134.4(3) . . ?
C1 C6 H6 118.8 . . ?
C5 C6 C1 122.4(3) . . ?
C5 C6 H6 118.8 . . ?
C54 C55 H55 119.0 . . ?
C56 C55 C54 122.0(3) . . ?
C56 C55 H55 119.0 . . ?
O4 C16 C17 115.9(3) . . ?
C15 C16 O4 109.5(3) . . ?
C15 C16 C17 134.6(3) . . ?
N53 C58 H58A 109.2 . . ?
N53 C58 H58B 109.2 . . ?
N53 C58 C57 112.0(3) . . ?
H58A C58 H58B 107.9 . . ?
C57 C58 H58A 109.2 . . ?
C57 C58 H58B 109.2 . . ?
N3 C8 H8A 109.2 . . ?
N3 C8 H8B 109.2 . . ?
N3 C8 C7 111.9(3) . . ?
H8A C8 H8B 107.9 . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
N3 C12 H12A 109.7 . . ?
N3 C12 H12B 109.7 . . ?
N3 C12 C11 109.6(3) . . ?
H12A C12 H12B 108.2 . . ?
C11 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
N2 C7 C8 108.1(3) . . ?
N2 C7 H7A 110.1 . . ?
N2 C7 H7B 110.1 . . ?
C8 C7 H7A 110.1 . . ?
C8 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
N53 C59 H59A 109.7 . . ?
N53 C59 H59B 109.7 . . ?
N53 C59 C60 109.7(3) . . ?
H59A C59 H59B 108.2 . . ?
C60 C59 H59A 109.7 . . ?
C60 C59 H59B 109.7 . . ?
N3 C9 H9A 109.7 . . ?
N3 C9 H9B 109.7 . . ?
N3 C9 C10 110.0(3) . . ?
H9A C9 H9B 108.2 . . ?
C10 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
C13 C14 H14 126.5 . . ?
C13 C14 C15 106.9(3) . . ?
C15 C14 H14 126.5 . . ?
N53 C62 H62A 109.8 . . ?
N53 C62 H62B 109.8 . . ?
N53 C62 C61 109.5(3) . . ?
H62A C62 H62B 108.2 . . ?
C61 C62 H62A 109.8 . . ?
C61 C62 H62B 109.8 . . ?
N52 C57 C58 108.6(3) . . ?
N52 C57 H57A 110.0 . . ?
N52 C57 H57B 110.0 . . ?
C58 C57 H57A 110.0 . . ?
C58 C57 H57B 110.0 . . ?
H57A C57 H57B 108.3 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C64 C65 H65 126.5 . . ?
C66 C65 C64 107.0(3) . . ?
C66 C65 H65 126.5 . . ?
C16 C15 C14 107.0(3) . . ?
C16 C15 H15 126.5 . . ?
C14 C15 H15 126.5 . . ?
O53 C60 C59 111.6(3) . . ?
O53 C60 H60A 109.3 . . ?
O53 C60 H60B 109.3 . . ?
C59 C60 H60A 109.3 . . ?
C59 C60 H60B 109.3 . . ?
H60A C60 H60B 108.0 . . ?
O53 C61 C62 112.0(3) . . ?
O53 C61 H61A 109.2 . . ?
O53 C61 H61B 109.2 . . ?
C62 C61 H61A 109.2 . . ?
C62 C61 H61B 109.2 . . ?
H61A C61 H61B 107.9 . . ?
O3 C10 C9 111.4(3) . . ?
O3 C10 H10A 109.3 . . ?
O3 C10 H10B 109.3 . . ?
C9 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
O3 C11 C12 111.8(3) . . ?
O3 C11 H11A 109.3 . . ?
O3 C11 H11B 109.3 . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C66 C67 H67A 109.5 . . ?
C66 C67 H67B 109.5 . . ?
C66 C67 H67C 109.5 . . ?
H67A C67 H67B 109.5 . . ?
H67A C67 H67C 109.5 . . ?
H67B C67 H67C 109.5 . . ?

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
O54 C66 C65 C64 0.1(4) . . . . ?
O4 C13 C14 C15 -1.3(4) . . . . ?
O4 C16 C15 C14 -0.8(4) . . . . ?
O51 N51 C52 C53 -173.1(3) . . . . ?
O51 N51 C52 C51 7.3(5) . . . . ?
O1 N1 C2 C3 170.0(3) . . . . ?
O1 N1 C2 C1 -10.8(5) . . . . ?
O52 N51 C52 C53 6.6(5) . . . . ?
O52 N51 C52 C51 -173.1(3) . . . . ?
O2 N1 C2 C3 -9.4(5) . . . . ?
O2 N1 C2 C1 169.7(3) . . . . ?
N51 C52 C53 C54 -179.8(3) . . . . ?
N51 C52 C51 N52 0.2(5) . . . . ?
N51 C52 C51 C56 178.2(3) . . . . ?
N53 C58 C57 N52 -56.1(4) . . . . ?
N53 C59 C60 O53 58.7(4) . . . . ?
N53 C62 C61 O53 -58.0(4) . . . . ?
N52 C51 C56 C55 179.5(3) . . . . ?
N3 C8 C7 N2 56.5(4) . . . . ?
N3 C12 C11 O3 -58.8(4) . . . . ?
N3 C9 C10 O3 58.3(4) . . . . ?
N2 C1 C2 N1 -0.4(5) . . . . ?
N2 C1 C2 C3 178.6(3) . . . . ?
N2 C1 C6 C5 -179.3(3) . . . . ?
C4 C3 C2 N1 179.1(3) . . . . ?
C4 C3 C2 C1 0.0(5) . . . . ?
C4 C13 C14 C15 178.0(4) . . . . ?
C4 C5 C6 C1 1.1(5) . . . . ?
C3 C4 C13 O4 175.0(3) . . . . ?
C3 C4 C13 C14 -4.2(7) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
C1 N2 C7 C8 -177.2(3) . . . . ?
C52 C53 C54 C63 -179.7(3) . . . . ?
C52 C53 C54 C55 1.6(5) . . . . ?
C52 C51 C56 C55 1.4(5) . . . . ?
C53 C52 C51 N52 -179.4(3) . . . . ?
C53 C52 C51 C56 -1.4(5) . . . . ?
C53 C54 C63 O54 -173.5(3) . . . . ?
C53 C54 C63 C64 5.4(6) . . . . ?
C53 C54 C55 C56 -1.6(5) . . . . ?
C51 N52 C57 C58 -179.8(3) . . . . ?
C51 C52 C53 C54 -0.1(5) . . . . ?
C51 C56 C55 C54 0.0(5) . . . . ?
C13 O4 C16 C17 -179.8(3) . . . . ?
C13 O4 C16 C15 0.0(4) . . . . ?
C13 C4 C3 C2 179.9(3) . . . . ?
C13 C4 C5 C6 179.6(3) . . . . ?
C13 C14 C15 C16 1.3(4) . . . . ?
C66 O54 C63 C64 -0.7(4) . . . . ?
C66 O54 C63 C54 178.5(3) . . . . ?
C5 C4 C3 C2 -0.7(5) . . . . ?
C5 C4 C13 O4 -4.3(5) . . . . ?
C5 C4 C13 C14 176.4(4) . . . . ?
C2 C1 C6 C5 -1.8(5) . . . . ?
C63 O54 C66 C65 0.4(4) . . . . ?
C63 O54 C66 C67 -179.7(3) . . . . ?
C63 C64 C65 C66 -0.5(4) . . . . ?
C63 C54 C55 C56 179.7(3) . . . . ?
C6 C1 C2 N1 -177.8(3) . . . . ?
C6 C1 C2 C3 1.2(5) . . . . ?
C55 C54 C63 O54 5.1(5) . . . . ?
C55 C54 C63 C64 -176.0(4) . . . . ?
C16 O4 C13 C4 -178.6(3) . . . . ?
C16 O4 C13 C14 0.8(4) . . . . ?
C58 N53 C59 C60 177.2(3) . . . . ?
C58 N53 C62 C61 -178.0(3) . . . . ?
C8 N3 C12 C11 -177.9(3) . . . . ?
C8 N3 C9 C10 178.7(3) . . . . ?
C12 N3 C8 C7 72.9(4) . . . . ?
C12 N3 C9 C10 -57.8(4) . . . . ?
C7 N2 C1 C2 175.4(3) . . . . ?
C7 N2 C1 C6 -7.3(5) . . . . ?
C59 N53 C58 C57 -73.8(4) . . . . ?
C59 N53 C62 C61 57.7(4) . . . . ?
C9 N3 C8 C7 -165.1(3) . . . . ?
C9 N3 C12 C11 57.9(4) . . . . ?
C62 N53 C58 C57 163.5(3) . . . . ?
C62 N53 C59 C60 -58.2(4) . . . . ?
C57 N52 C51 C52 -175.8(3) . . . . ?
C57 N52 C51 C56 6.2(5) . . . . ?
C17 C16 C15 C14 179.0(4) . . . . ?
C65 C64 C63 O54 0.7(4) . . . . ?
C65 C64 C63 C54 -178.3(4) . . . . ?
C60 O53 C61 C62 57.3(4) . . . . ?
C61 O53 C60 C59 -57.4(4) . . . . ?
C10 O3 C11 C12 57.9(4) . . . . ?
C11 O3 C10 C9 -57.3(4) . . . . ?
C67 C66 C65 C64 -179.9(4) . . . . ?

_olex2_date_sample_data_collection 2019-04-04
_olex2_date_sample_submission    2019-03-12
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id AKE-020
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.600
_oxdiff_exptl_absorpt_empirical_full_min 0.678
####################################################################### 
# 
# 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_19
_database_code_depnum_ccdc_archive 'CCDC 2110088'
loop_
_audit_author_name
_audit_author_address
'Graham Tizzard'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2021-09-15 deposited with the CCDC.	2022-04-25 downloaded from the CCDC.
;

#2018ncs0434z

_audit_creation_date             2021-09-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H19 Cl N4 O3'
_chemical_formula_sum            'C17 H19 Cl N4 O3'
_chemical_formula_weight         362.81
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H19 Cl N4 O3'
_chemical_oxdiff_usercomment     AKE-021
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   31.8053(5)
_cell_length_b                   14.6164(3)
_cell_length_c                   7.25740(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3373.81(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    15414
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.6420
_cell_measurement_theta_min      2.3430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1520
_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of DCM and hexane  by slow evaporation'
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            39012
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.700
_diffrn_reflns_theta_min         1.533
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -104.00  26.00   0.50   20.00    --  -14.80 -70.00 -60.00  260
  2  ω   -104.00  26.00   0.50   20.00    --  -14.80 -70.00  60.00  260
  3  ω    -55.00  75.00   0.50   20.00    --  -14.80  70.00 -90.00  260
  4  ω    -52.00  51.00   0.50   20.00    --  -14.80  57.00 150.00  206
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_details 'Rigaku, AFC12 κ goniometer'
_diffrn_measurement_device_type  
'Rigaku FRE+ equipped with VHF Varimax confocal mirrors and an AFC12 goniometer and HyPix 6000 detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0006561000
_diffrn_orient_matrix_UB_12      -0.0484615000
_diffrn_orient_matrix_UB_13      -0.0048952000
_diffrn_orient_matrix_UB_21      0.0133263000
_diffrn_orient_matrix_UB_22      -0.0027979000
_diffrn_orient_matrix_UB_23      0.0781643000
_diffrn_orient_matrix_UB_31      -0.0178648000
_diffrn_orient_matrix_UB_32      -0.0002687000
_diffrn_orient_matrix_UB_33      0.0584448000
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3726
_reflns_number_total             4341
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4341
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0445P)²+1.4654P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0895
_refine_special_details          
'H-atom (H3) bonded to heteroatom (N3) was located in the difference map and refined with a riding model and distance restraint.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 N2-H2
 0.86 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C12(H12A,H12B), C11(H11A,H11B), C10(H10A,H10B),
 C9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C5(H5), C14(H14), C15(H15), C17(H17)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.26675(2) 0.91206(2) 0.66691(5) 0.02913(10) Uani 1 1 d . . . . .
O2 O 0.52954(3) 0.94261(6) 0.34975(13) 0.02253(19) Uani 1 1 d . . . . .
O1 O 0.57563(3) 0.83610(6) 0.30517(13) 0.0231(2) Uani 1 1 d . . . . .
O3 O 0.71710(3) 0.62096(7) 0.51025(14) 0.0286(2) Uani 1 1 d . . . . .
N4 N 0.34847(3) 0.91993(7) 0.64228(13) 0.0168(2) Uani 1 1 d . . . . .
N1 N 0.53949(3) 0.86072(7) 0.34532(13) 0.01533(19) Uani 1 1 d . . . . .
N2 N 0.55418(3) 0.66217(7) 0.31434(14) 0.0151(2) Uani 1 1 d D . . . .
H2 H 0.5754(4) 0.6982(9) 0.304(2) 0.018 Uiso 1 1 d D U . . .
N3 N 0.63812(3) 0.60001(7) 0.32821(13) 0.0154(2) Uani 1 1 d . . . . .
C4 C 0.43602(3) 0.76506(7) 0.48258(14) 0.0126(2) Uani 1 1 d . . . . .
C3 C 0.46849(3) 0.82455(8) 0.44095(15) 0.0134(2) Uani 1 1 d . . . . .
H3 H 0.463866 0.887274 0.448224 0.016 Uiso 1 1 calc R U . . .
C2 C 0.50819(3) 0.79236(7) 0.38806(15) 0.0130(2) Uani 1 1 d . . . . .
C1 C 0.51716(3) 0.69745(7) 0.37198(15) 0.0129(2) Uani 1 1 d . . . . .
C6 C 0.48334(3) 0.63799(7) 0.41801(15) 0.0148(2) Uani 1 1 d . . . . .
H6 H 0.487462 0.575086 0.411324 0.018 Uiso 1 1 calc R U . . .
C5 C 0.44486(3) 0.67069(8) 0.47195(15) 0.0145(2) Uani 1 1 d . . . . .
H5 H 0.423851 0.629142 0.502606 0.017 Uiso 1 1 calc R U . . .
C13 C 0.39339(3) 0.79838(8) 0.53050(15) 0.0133(2) Uani 1 1 d . . . . .
C14 C 0.35758(3) 0.74409(8) 0.50202(16) 0.0171(2) Uani 1 1 d . . . . .
H14 H 0.360417 0.685150 0.455401 0.021 Uiso 1 1 calc R U . . .
C15 C 0.31808(4) 0.77803(9) 0.54312(17) 0.0201(2) Uani 1 1 d . . . . .
H15 H 0.294036 0.742907 0.525281 0.024 Uiso 1 1 calc R U . . .
C16 C 0.31567(3) 0.86624(9) 0.61181(16) 0.0179(2) Uani 1 1 d . . . . .
C17 C 0.38652(3) 0.88560(8) 0.60233(15) 0.0147(2) Uani 1 1 d . . . . .
H17 H 0.409859 0.922404 0.623972 0.018 Uiso 1 1 calc R U . . .
C7 C 0.56259(4) 0.56446(8) 0.30885(17) 0.0177(2) Uani 1 1 d . . . . .
H7A H 0.541604 0.533957 0.233809 0.021 Uiso 1 1 calc R U . . .
H7B H 0.561270 0.539224 0.432334 0.021 Uiso 1 1 calc R U . . .
C8 C 0.60613(3) 0.54897(8) 0.22769(16) 0.0176(2) Uani 1 1 d . . . . .
H8A H 0.612776 0.484239 0.231944 0.021 Uiso 1 1 calc R U . . .
H8B H 0.606221 0.567944 0.099614 0.021 Uiso 1 1 calc R U . . .
C12 C 0.64646(4) 0.55936(8) 0.50900(16) 0.0188(2) Uani 1 1 d . . . . .
H12A H 0.656735 0.497342 0.493591 0.023 Uiso 1 1 calc R U . . .
H12B H 0.620630 0.556905 0.579904 0.023 Uiso 1 1 calc R U . . .
C11 C 0.67877(4) 0.61572(9) 0.61081(18) 0.0232(3) Uani 1 1 d . . . . .
H11A H 0.667873 0.676929 0.630507 0.028 Uiso 1 1 calc R U . . .
H11B H 0.684076 0.588456 0.730427 0.028 Uiso 1 1 calc R U . . .
C10 C 0.70956(4) 0.66009(10) 0.33322(19) 0.0275(3) Uani 1 1 d . . . . .
H10A H 0.735756 0.662734 0.264989 0.033 Uiso 1 1 calc R U . . .
H10B H 0.699283 0.722133 0.348061 0.033 Uiso 1 1 calc R U . . .
C9 C 0.67773(4) 0.60477(9) 0.22525(18) 0.0217(3) Uani 1 1 d . . . . .
H9A H 0.672904 0.633164 0.106316 0.026 Uiso 1 1 calc R U . . .
H9B H 0.688467 0.543513 0.204513 0.026 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
Cl1 C16 1.7404(12) . ?
O2 N1 1.2385(13) . ?
O1 N1 1.2392(12) . ?
O3 C11 1.4228(16) . ?
O3 C10 1.4266(16) . ?
N4 C16 1.3242(15) . ?
N4 C17 1.3418(14) . ?
N1 C2 1.4441(14) . ?
N2 H2 0.858(9) . ?
N2 C1 1.3518(14) . ?
N2 C7 1.4535(15) . ?
N3 C8 1.4574(15) . ?
N3 C12 1.4646(15) . ?
N3 C9 1.4664(14) . ?
C4 C3 1.3835(15) . ?
C4 C5 1.4100(16) . ?
C4 C13 1.4819(14) . ?
C3 H3 0.9300 . ?
C3 C2 1.4011(15) . ?
C2 C1 1.4211(15) . ?
C1 C6 1.4226(15) . ?
C6 H6 0.9300 . ?
C6 C5 1.3709(15) . ?
C5 H5 0.9300 . ?
C13 C14 1.4033(15) . ?
C13 C17 1.3946(16) . ?
C14 H14 0.9300 . ?
C14 C15 1.3834(16) . ?
C15 H15 0.9300 . ?
C15 C16 1.3844(17) . ?
C17 H17 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.5217(16) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.5102(17) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C9 1.5141(18) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O3 C10 109.85(9) . . ?
C16 N4 C17 116.93(10) . . ?
O2 N1 O1 121.60(9) . . ?
O2 N1 C2 119.13(9) . . ?
O1 N1 C2 119.27(9) . . ?
C1 N2 H2 118.5(10) . . ?
C1 N2 C7 122.93(10) . . ?
C7 N2 H2 117.1(10) . . ?
C8 N3 C12 111.54(9) . . ?
C8 N3 C9 111.66(9) . . ?
C12 N3 C9 108.67(9) . . ?
C3 C4 C5 116.99(10) . . ?
C3 C4 C13 121.85(10) . . ?
C5 C4 C13 121.12(10) . . ?
C4 C3 H3 119.3 . . ?
C4 C3 C2 121.44(10) . . ?
C2 C3 H3 119.3 . . ?
C3 C2 N1 116.60(10) . . ?
C3 C2 C1 122.09(10) . . ?
C1 C2 N1 121.29(10) . . ?
N2 C1 C2 124.94(10) . . ?
N2 C1 C6 119.88(10) . . ?
C2 C1 C6 115.17(10) . . ?
C1 C6 H6 119.0 . . ?
C5 C6 C1 121.94(10) . . ?
C5 C6 H6 119.0 . . ?
C4 C5 H5 118.8 . . ?
C6 C5 C4 122.33(10) . . ?
C6 C5 H5 118.8 . . ?
C14 C13 C4 121.48(10) . . ?
C17 C13 C4 122.10(10) . . ?
C17 C13 C14 116.41(10) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.17(11) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 121.2 . . ?
C14 C15 C16 117.50(11) . . ?
C16 C15 H15 121.2 . . ?
N4 C16 Cl1 115.97(9) . . ?
N4 C16 C15 124.64(11) . . ?
C15 C16 Cl1 119.38(9) . . ?
N4 C17 C13 124.32(10) . . ?
N4 C17 H17 117.8 . . ?
C13 C17 H17 117.8 . . ?
N2 C7 H7A 109.9 . . ?
N2 C7 H7B 109.9 . . ?
N2 C7 C8 108.92(9) . . ?
H7A C7 H7B 108.3 . . ?
C8 C7 H7A 109.9 . . ?
C8 C7 H7B 109.9 . . ?
N3 C8 C7 111.43(9) . . ?
N3 C8 H8A 109.3 . . ?
N3 C8 H8B 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
N3 C12 H12A 109.7 . . ?
N3 C12 H12B 109.7 . . ?
N3 C12 C11 109.89(10) . . ?
H12A C12 H12B 108.2 . . ?
C11 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
O3 C11 C12 111.18(10) . . ?
O3 C11 H11A 109.4 . . ?
O3 C11 H11B 109.4 . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
O3 C10 H10A 109.4 . . ?
O3 C10 H10B 109.4 . . ?
O3 C10 C9 111.36(11) . . ?
H10A C10 H10B 108.0 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
N3 C9 C10 109.64(10) . . ?
N3 C9 H9A 109.7 . . ?
N3 C9 H9B 109.7 . . ?
C10 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O1 0.858(9) 2.016(13) 2.6330(13) 128.0(12) . yes

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
O2 N1 C2 C3 -2.95(15) . . . . ?
O2 N1 C2 C1 175.38(10) . . . . ?
O1 N1 C2 C3 177.04(10) . . . . ?
O1 N1 C2 C1 -4.63(16) . . . . ?
O3 C10 C9 N3 58.68(14) . . . . ?
N1 C2 C1 N2 -1.14(17) . . . . ?
N1 C2 C1 C6 -179.81(10) . . . . ?
N2 C1 C6 C5 -178.07(10) . . . . ?
N2 C7 C8 N3 54.87(13) . . . . ?
N3 C12 C11 O3 -59.19(13) . . . . ?
C4 C3 C2 N1 179.13(10) . . . . ?
C4 C3 C2 C1 0.82(17) . . . . ?
C4 C13 C14 C15 -178.12(11) . . . . ?
C4 C13 C17 N4 177.77(10) . . . . ?
C3 C4 C5 C6 -1.82(16) . . . . ?
C3 C4 C13 C14 154.43(11) . . . . ?
C3 C4 C13 C17 -24.18(16) . . . . ?
C3 C2 C1 N2 177.09(10) . . . . ?
C3 C2 C1 C6 -1.58(16) . . . . ?
C2 C1 C6 C5 0.67(16) . . . . ?
C1 N2 C7 C8 176.98(10) . . . . ?
C1 C6 C5 C4 1.04(17) . . . . ?
C5 C4 C3 C2 0.89(16) . . . . ?
C5 C4 C13 C14 -23.58(16) . . . . ?
C5 C4 C13 C17 157.80(11) . . . . ?
C13 C4 C3 C2 -177.20(10) . . . . ?
C13 C4 C5 C6 176.29(10) . . . . ?
C13 C14 C15 C16 0.13(18) . . . . ?
C14 C13 C17 N4 -0.91(17) . . . . ?
C14 C15 C16 Cl1 -179.67(9) . . . . ?
C14 C15 C16 N4 -0.61(19) . . . . ?
C16 N4 C17 C13 0.49(17) . . . . ?
C17 N4 C16 Cl1 179.40(8) . . . . ?
C17 N4 C16 C15 0.31(18) . . . . ?
C17 C13 C14 C15 0.57(17) . . . . ?
C7 N2 C1 C2 176.84(11) . . . . ?
C7 N2 C1 C6 -4.55(16) . . . . ?
C8 N3 C12 C11 -178.33(10) . . . . ?
C8 N3 C9 C10 178.76(10) . . . . ?
C12 N3 C8 C7 72.82(12) . . . . ?
C12 N3 C9 C10 -57.79(13) . . . . ?
C11 O3 C10 C9 -58.34(14) . . . . ?
C10 O3 C11 C12 58.45(14) . . . . ?
C9 N3 C8 C7 -165.38(10) . . . . ?
C9 N3 C12 C11 58.15(13) . . . . ?

_olex2_date_sample_data_collection 2018-06-13
_olex2_date_sample_submission    2018-05-16
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id AKE-021
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.769
_oxdiff_exptl_absorpt_empirical_full_min 0.434
####################################################################### 
# 
# 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_27
_database_code_depnum_ccdc_archive 'CCDC 2110090'
loop_
_audit_author_name
_audit_author_address
'Graham Tizzard'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2021-09-15 deposited with the CCDC.	2022-04-25 downloaded from the CCDC.
;

#2018ncs0435z

_audit_creation_date             2018-06-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H31 N3 O4'
_chemical_formula_sum            'C26 H31 N3 O4'
_chemical_formula_weight         449.54
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C26 H31 N3 O4'
_chemical_oxdiff_usercomment     AKE-040
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   13.0873(2)
_cell_length_b                   12.4610(2)
_cell_length_c                   14.1989(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.111(2)
_cell_angle_gamma                90
_cell_volume                     2306.36(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14788
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.7150
_cell_measurement_theta_min      2.1600
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60409
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of DCM and hexane  by slow evaporation'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            35410
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_min         2.178
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00  76.00   0.50    5.00    --  -13.80 -11.00 117.00  358
  2  ω    -47.00  76.00   0.50    5.00    --  -13.80  57.00 -60.00  246
  3  ω   -103.00  20.00   0.50    5.00    --  -13.80 -57.00 -30.00  246
  4  ω    -47.00 -16.00   0.50    5.00    --  -13.80  57.00-180.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_details 'Rigaku, AFC12 κ goniometer'
_diffrn_measurement_device_type  
'Rigaku FRE+ equipped with VHF Varimax confocal mirrors and an AFC12 goniometer and HyPix 6000 detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0399743000
_diffrn_orient_matrix_UB_12      -0.0074809000
_diffrn_orient_matrix_UB_13      -0.0365492000
_diffrn_orient_matrix_UB_21      0.0368291000
_diffrn_orient_matrix_UB_22      -0.0033762000
_diffrn_orient_matrix_UB_23      -0.0336349000
_diffrn_orient_matrix_UB_31      0.0030790000
_diffrn_orient_matrix_UB_32      -0.0563098000
_diffrn_orient_matrix_UB_33      0.0068780000
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, VHF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5892
_reflns_number_total             7030
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         7030
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0496
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0793P)²+0.6574P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1330
_refine_ls_wR_factor_ref         0.1390
_refine_special_details          
'H-atoms bonded to O-atoms were located in the difference map and refined with the riding model and distance restraint.  The H-atom bonded to O3/O4 is disordered over two positions (ca. 43:57 respectively)'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O2-H2 = O3-H3 = O4-H4
 0.82 with sigma of 0.01
3. Others
 Sof(H4)=1-FVAR(1)
 Sof(H3)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4A), C6(H6), C7(H7), C17(H17), C18(H18), C20(H20), C21(H21)
4.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.75994(7) 0.34312(7) 0.13350(6) 0.02886(19) Uani 1 1 d . . . . .
O2 O 0.47616(7) 0.28293(8) 0.98593(6) 0.0295(2) Uani 1 1 d D . . . .
H2 H 0.4336(12) 0.2336(12) 0.9750(13) 0.044 Uiso 1 1 d DR . . . .
O3 O 0.89953(9) 1.05487(8) 0.33675(9) 0.0409(3) Uani 1 1 d D . . . .
H3 H 0.904(4) 1.036(5) 0.2807(15) 0.061 Uiso 0.43(4) 1 d DR . P A 1
O4 O 0.90737(8) 0.95790(9) 0.18918(8) 0.0373(2) Uani 1 1 d D . . . .
H4 H 0.899(3) 1.002(3) 0.233(2) 0.056 Uiso 0.57(4) 1 d DR . P A 2
N1 N 0.77156(7) 0.48299(7) 0.50231(6) 0.01850(18) Uani 1 1 d . . . . .
N2 N 0.66364(7) 0.62055(7) 0.51530(7) 0.02043(18) Uani 1 1 d . . . . .
N3 N 0.74916(7) 0.35081(8) 0.33358(6) 0.02059(19) Uani 1 1 d . . . . .
C1 C 0.81074(8) 0.56739(8) 0.45396(7) 0.0182(2) Uani 1 1 d . . . . .
C2 C 0.68491(9) 0.51935(9) 0.53840(7) 0.0197(2) Uani 1 1 d . . . . .
C3 C 0.74191(8) 0.65238(8) 0.46131(7) 0.0185(2) Uani 1 1 d . . . . .
C4 C 0.75828(8) 0.75133(9) 0.41940(8) 0.0203(2) Uani 1 1 d . . . . .
H4A H 0.709649 0.807707 0.421316 0.024 Uiso 1 1 calc R . . . .
C5 C 0.84765(8) 0.76534(9) 0.37471(8) 0.0200(2) Uani 1 1 d . . . . .
C6 C 0.91864(8) 0.68006(9) 0.37329(8) 0.0213(2) Uani 1 1 d . . . . .
H6 H 0.980884 0.691882 0.345182 0.026 Uiso 1 1 calc R . . . .
C7 C 0.90135(8) 0.58010(9) 0.41110(8) 0.0209(2) Uani 1 1 d . . . . .
H7 H 0.949026 0.522999 0.407919 0.025 Uiso 1 1 calc R . . . .
C8 C 0.80937(9) 0.37288(8) 0.50328(8) 0.0212(2) Uani 1 1 d . . . . .
H8A H 0.803368 0.341030 0.566424 0.025 Uiso 1 1 calc R . . . .
H8B H 0.882819 0.372931 0.491574 0.025 Uiso 1 1 calc R . . . .
C9 C 0.74912(9) 0.30457(9) 0.42813(8) 0.0229(2) Uani 1 1 d . . . . .
H9A H 0.779523 0.231816 0.428114 0.027 Uiso 1 1 calc R . . . .
H9B H 0.677440 0.297412 0.444406 0.027 Uiso 1 1 calc R . . . .
C10 C 0.84529(9) 0.33109(10) 0.29170(8) 0.0251(2) Uani 1 1 d . . . . .
H10A H 0.855935 0.252887 0.285142 0.030 Uiso 1 1 calc R . . . .
H10B H 0.903319 0.360404 0.333365 0.030 Uiso 1 1 calc R . . . .
C11 C 0.84186(10) 0.38397(11) 0.19575(9) 0.0280(2) Uani 1 1 d . . . . .
H11A H 0.833225 0.462378 0.202995 0.034 Uiso 1 1 calc R . . . .
H11B H 0.907650 0.371387 0.168123 0.034 Uiso 1 1 calc R . . . .
C12 C 0.66452(10) 0.36073(11) 0.17311(9) 0.0284(2) Uani 1 1 d . . . . .
H12A H 0.607869 0.330471 0.130357 0.034 Uiso 1 1 calc R . . . .
H12B H 0.652570 0.438819 0.178819 0.034 Uiso 1 1 calc R . . . .
C13 C 0.66464(9) 0.30884(10) 0.26969(8) 0.0257(2) Uani 1 1 d . . . . .
H13A H 0.598624 0.323505 0.296238 0.031 Uiso 1 1 calc R . . . .
H13B H 0.671955 0.230135 0.263536 0.031 Uiso 1 1 calc R . . . .
C14 C 0.62836(10) 0.45211(9) 0.60374(8) 0.0252(2) Uani 1 1 d . . . . .
H14A H 0.678513 0.419028 0.651433 0.030 Uiso 1 1 calc R . . . .
H14B H 0.592801 0.393392 0.567047 0.030 Uiso 1 1 calc R . . . .
C15 C 0.54970(10) 0.51496(10) 0.65470(9) 0.0261(2) Uani 1 1 d . . . . .
H15A H 0.577582 0.586894 0.671863 0.031 Uiso 1 1 calc R . . . .
H15B H 0.486583 0.524768 0.611703 0.031 Uiso 1 1 calc R . . . .
C16 C 0.52351(9) 0.45743(9) 0.74292(8) 0.0216(2) Uani 1 1 d . . . . .
C17 C 0.57897(9) 0.47759(10) 0.82932(8) 0.0257(2) Uani 1 1 d . . . . .
H17 H 0.630316 0.531680 0.832999 0.031 Uiso 1 1 calc R . . . .
C18 C 0.56114(10) 0.42062(10) 0.91033(8) 0.0269(2) Uani 1 1 d . . . . .
H18 H 0.599725 0.436091 0.968604 0.032 Uiso 1 1 calc R . . . .
C19 C 0.48651(9) 0.34076(9) 0.90576(8) 0.0218(2) Uani 1 1 d . . . . .
C20 C 0.42758(8) 0.32248(9) 0.82105(8) 0.0222(2) Uani 1 1 d . . . . .
H20 H 0.374062 0.270755 0.818064 0.027 Uiso 1 1 calc R . . . .
C21 C 0.44698(9) 0.37999(9) 0.74048(8) 0.0234(2) Uani 1 1 d . . . . .
H21 H 0.407036 0.365963 0.682604 0.028 Uiso 1 1 calc R . . . .
C22 C 0.86965(9) 0.86869(9) 0.32800(8) 0.0230(2) Uani 1 1 d . . . . .
C23 C 0.88533(9) 0.87059(10) 0.22996(9) 0.0274(2) Uani 1 1 d . . . . .
C24 C 0.87789(11) 0.77167(12) 0.16950(9) 0.0338(3) Uani 1 1 d . . . . .
H24A H 0.866642 0.792373 0.102792 0.051 Uiso 1 1 calc GR . . . .
H24B H 0.820389 0.727450 0.186480 0.051 Uiso 1 1 calc GR . . . .
H24C H 0.941762 0.730590 0.179721 0.051 Uiso 1 1 calc GR . . . .
C25 C 0.87761(10) 0.96525(10) 0.37793(10) 0.0292(3) Uani 1 1 d . . . . .
C26 C 0.86293(12) 0.97628(11) 0.48045(11) 0.0372(3) Uani 1 1 d . . . . .
H26A H 0.903255 1.037197 0.506882 0.056 Uiso 1 1 calc GR . . . .
H26B H 0.885731 0.910435 0.513728 0.056 Uiso 1 1 calc GR . . . .
H26C H 0.790149 0.988443 0.488089 0.056 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.4216(16) . ?
O1 C12 1.4314(15) . ?
O2 H2 0.835(9) . ?
O2 C19 1.3642(13) . ?
O3 H3 0.836(10) . ?
O3 C25 1.3043(15) . ?
O4 H4 0.840(10) . ?
O4 H4 0.840(10) . ?
O4 C23 1.2774(15) . ?
N1 C1 1.3795(13) . ?
N1 C2 1.3629(14) . ?
N1 C8 1.4582(13) . ?
N2 C2 1.3264(14) . ?
N2 C3 1.3907(13) . ?
N3 C9 1.4610(14) . ?
N3 C10 1.4594(14) . ?
N3 C13 1.4633(15) . ?
C1 C3 1.4001(14) . ?
C1 C7 1.3895(15) . ?
C2 C14 1.4941(15) . ?
C3 C4 1.3939(15) . ?
C4 H4A 0.9500 . ?
C4 C5 1.3905(15) . ?
C5 C6 1.4129(15) . ?
C5 C22 1.4884(15) . ?
C6 H6 0.9500 . ?
C6 C7 1.3829(15) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5280(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5104(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5160(17) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5264(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5090(15) . ?
C16 C17 1.3915(17) . ?
C16 C21 1.3890(16) . ?
C17 H17 0.9500 . ?
C17 C18 1.3889(16) . ?
C18 H18 0.9500 . ?
C18 C19 1.3918(16) . ?
C19 C20 1.3887(16) . ?
C20 H20 0.9500 . ?
C20 C21 1.3923(16) . ?
C21 H21 0.9500 . ?
C22 C23 1.4252(17) . ?
C22 C25 1.3959(17) . ?
C23 C24 1.500(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.491(2) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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
C11 O1 C12 109.68(9) . . ?
C19 O2 H2 110.4(13) . . ?
C25 O3 H3 103(4) . . ?
H4 O4 H4 0(5) . . ?
H4 O4 C23 100(3) . . ?
C23 O4 H4 100(3) . . ?
C1 N1 C8 125.54(9) . . ?
C2 N1 C1 106.99(9) . . ?
C2 N1 C8 127.03(9) . . ?
C2 N2 C3 105.00(9) . . ?
C9 N3 C13 111.51(9) . . ?
C10 N3 C9 112.26(9) . . ?
C10 N3 C13 108.58(9) . . ?
N1 C1 C3 105.64(9) . . ?
N1 C1 C7 132.41(10) . . ?
C7 C1 C3 121.76(10) . . ?
N1 C2 C14 121.45(10) . . ?
N2 C2 N1 112.73(9) . . ?
N2 C2 C14 125.60(10) . . ?
N2 C3 C1 109.61(9) . . ?
N2 C3 C4 129.52(10) . . ?
C4 C3 C1 120.86(10) . . ?
C3 C4 H4A 120.9 . . ?
C5 C4 C3 118.26(10) . . ?
C5 C4 H4A 120.9 . . ?
C4 C5 C6 119.54(10) . . ?
C4 C5 C22 121.06(10) . . ?
C6 C5 C22 119.40(10) . . ?
C5 C6 H6 118.6 . . ?
C7 C6 C5 122.78(10) . . ?
C7 C6 H6 118.6 . . ?
C1 C7 H7 121.7 . . ?
C6 C7 C1 116.63(10) . . ?
C6 C7 H7 121.7 . . ?
N1 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
N1 C8 C9 111.35(9) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
N3 C9 C8 112.31(9) . . ?
N3 C9 H9A 109.1 . . ?
N3 C9 H9B 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
N3 C10 H10A 109.7 . . ?
N3 C10 H10B 109.7 . . ?
N3 C10 C11 109.67(10) . . ?
H10A C10 H10B 108.2 . . ?
C11 C10 H10A 109.7 . . ?
C11 C10 H10B 109.7 . . ?
O1 C11 C10 111.40(10) . . ?
O1 C11 H11A 109.3 . . ?
O1 C11 H11B 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
O1 C12 H12A 109.4 . . ?
O1 C12 H12B 109.4 . . ?
O1 C12 C13 111.06(10) . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
N3 C13 C12 110.38(10) . . ?
N3 C13 H13A 109.6 . . ?
N3 C13 H13B 109.6 . . ?
C12 C13 H13A 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C2 C14 H14A 108.9 . . ?
C2 C14 H14B 108.9 . . ?
C2 C14 C15 113.51(10) . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C14 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 C14 111.25(10) . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C17 C16 C15 120.46(10) . . ?
C21 C16 C15 121.73(11) . . ?
C21 C16 C17 117.76(10) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 C16 121.66(11) . . ?
C18 C17 H17 119.2 . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.73(11) . . ?
C19 C18 H18 120.1 . . ?
O2 C19 C18 117.41(10) . . ?
O2 C19 C20 123.19(10) . . ?
C20 C19 C18 119.40(10) . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 119.96(10) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 C20 121.39(11) . . ?
C16 C21 H21 119.3 . . ?
C20 C21 H21 119.3 . . ?
C23 C22 C5 120.01(11) . . ?
C25 C22 C5 121.88(11) . . ?
C25 C22 C23 118.10(11) . . ?
O4 C23 C22 120.99(12) . . ?
O4 C23 C24 116.49(12) . . ?
C22 C23 C24 122.52(11) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O3 C25 C22 121.32(12) . . ?
O3 C25 C26 114.29(12) . . ?
C22 C25 C26 124.39(11) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 N2 0.835(9) 1.911(10) 2.7269(13) 165.2(19) 2_646 yes
O3 H3 O4 0.836(10) 1.63(2) 2.4289(16) 159(6) . yes
O4 H4 O3 0.840(10) 1.618(17) 2.4289(16) 161(4) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C12 C13 N3 57.93(13) . . . . ?
O2 C19 C20 C21 -175.80(11) . . . . ?
H4 O4 C23 C22 -8(3) . . . . ?
H4 O4 C23 C24 172(3) . . . . ?
N1 C1 C3 N2 1.44(12) . . . . ?
N1 C1 C3 C4 -179.71(10) . . . . ?
N1 C1 C7 C6 -176.10(11) . . . . ?
N1 C2 C14 C15 166.20(10) . . . . ?
N1 C8 C9 N3 55.34(12) . . . . ?
N2 C2 C14 C15 -8.00(17) . . . . ?
N2 C3 C4 C5 175.01(11) . . . . ?
N3 C10 C11 O1 -59.96(13) . . . . ?
C1 N1 C2 N2 1.40(12) . . . . ?
C1 N1 C2 C14 -173.49(10) . . . . ?
C1 N1 C8 C9 -94.33(12) . . . . ?
C1 C3 C4 C5 -3.58(16) . . . . ?
C2 N1 C1 C3 -1.67(11) . . . . ?
C2 N1 C1 C7 173.10(12) . . . . ?
C2 N1 C8 C9 77.08(13) . . . . ?
C2 N2 C3 C1 -0.62(12) . . . . ?
C2 N2 C3 C4 -179.34(11) . . . . ?
C2 C14 C15 C16 -159.19(10) . . . . ?
C3 N2 C2 N1 -0.48(12) . . . . ?
C3 N2 C2 C14 174.16(11) . . . . ?
C3 C1 C7 C6 -2.02(16) . . . . ?
C3 C4 C5 C6 -0.18(16) . . . . ?
C3 C4 C5 C22 179.60(10) . . . . ?
C4 C5 C6 C7 2.99(17) . . . . ?
C4 C5 C22 C23 -121.71(12) . . . . ?
C4 C5 C22 C25 59.59(16) . . . . ?
C5 C6 C7 C1 -1.85(17) . . . . ?
C5 C22 C23 O4 -177.86(11) . . . . ?
C5 C22 C23 C24 1.68(17) . . . . ?
C5 C22 C25 O3 178.21(11) . . . . ?
C5 C22 C25 C26 -1.51(19) . . . . ?
C6 C5 C22 C23 58.07(15) . . . . ?
C6 C5 C22 C25 -120.63(13) . . . . ?
C7 C1 C3 N2 -174.02(10) . . . . ?
C7 C1 C3 C4 4.82(16) . . . . ?
C8 N1 C1 C3 171.16(10) . . . . ?
C8 N1 C1 C7 -14.06(18) . . . . ?
C8 N1 C2 N2 -171.30(10) . . . . ?
C8 N1 C2 C14 13.81(16) . . . . ?
C9 N3 C10 C11 -178.08(9) . . . . ?
C9 N3 C13 C12 178.21(9) . . . . ?
C10 N3 C9 C8 78.18(12) . . . . ?
C10 N3 C13 C12 -57.59(12) . . . . ?
C11 O1 C12 C13 -57.61(13) . . . . ?
C12 O1 C11 C10 58.85(13) . . . . ?
C13 N3 C9 C8 -159.72(10) . . . . ?
C13 N3 C10 C11 58.17(12) . . . . ?
C14 C15 C16 C17 90.43(14) . . . . ?
C14 C15 C16 C21 -86.84(14) . . . . ?
C15 C16 C17 C18 -175.57(11) . . . . ?
C15 C16 C21 C20 175.92(11) . . . . ?
C16 C17 C18 C19 0.35(19) . . . . ?
C17 C16 C21 C20 -1.42(17) . . . . ?
C17 C18 C19 O2 176.23(11) . . . . ?
C17 C18 C19 C20 -2.92(18) . . . . ?
C18 C19 C20 C21 3.30(17) . . . . ?
C19 C20 C21 C16 -1.12(18) . . . . ?
C21 C16 C17 C18 1.81(18) . . . . ?
C22 C5 C6 C7 -176.80(11) . . . . ?
C23 C22 C25 O3 -0.52(18) . . . . ?
C23 C22 C25 C26 179.76(12) . . . . ?
C25 C22 C23 O4 0.89(18) . . . . ?
C25 C22 C23 C24 -179.57(11) . . . . ?

_olex2_date_sample_data_collection 2018-06-15
_olex2_date_sample_submission    2018-05-16
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id AKE-040
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.563
_oxdiff_exptl_absorpt_empirical_full_min 0.509
####################################################################### 
# 
# 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_20
_database_code_depnum_ccdc_archive 'CCDC 2110089'
loop_
_audit_author_name
_audit_author_address
'Graham Tizzard'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2021-09-15 deposited with the CCDC.	2022-04-25 downloaded from the CCDC.
;

#2019ncs0244z

_audit_creation_date             2021-09-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
?
?
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H19 F N4 O3'
_chemical_formula_sum            'C17 H19 F N4 O3'
_chemical_formula_weight         346.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H16 F N4 O3'
_chemical_oxdiff_usercomment     AKE-052
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'
F F 0.0727 0.0534 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.59320(10)
_cell_length_b                   7.25830(10)
_cell_length_c                   31.5918(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.7490(10)
_cell_angle_gamma                90
_cell_volume                     3263.76(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    15025
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.8190
_cell_measurement_theta_min      2.8900
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.900
_exptl_absorpt_coefficient_mu    0.893
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75437
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.47a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1456
_exptl_crystal_recrystallization_method 
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            31409
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.052
_diffrn_reflns_theta_min         3.119
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'hybrid pixel detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_dtime           0.000
_diffrn_detector_type            'Rigaku, HyPix 6000'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -142.00  37.00   0.50    0.75    --  -52.30  55.00-100.00  358
  2  ω    -75.00 -26.00   0.50    3.00    --  -90.00  55.00-100.00   98
  3  ω   -173.00 -90.00   0.50    3.00    --  -90.00  55.00-100.00  166
  4  ω    -19.00   6.00   0.50    0.75    --    5.00  55.00-100.00   50
  5  ω    -83.00  91.00   0.50    0.75    --    5.00   0.00-180.00  348
  6  ω   -157.00-123.00   0.50    3.00    --  -90.00  49.00-180.00   68
  7  ω   -153.00  -2.00   0.50    3.00    --  -90.00  20.00 -30.00  302
  8  ω   -170.00-136.00   0.50    3.00    --  -90.00  30.00 120.00   68
  9  ω    -55.00 -29.00   0.50    3.00    --  -90.00  30.00 120.00   52
 10  ω   -143.00 -94.00   0.50    3.00    --  -90.00  39.00-120.00   98
 11  ω   -178.00-152.00   0.50    3.00    --  -90.00  39.00-120.00   52
 12  ω    -57.00 -15.00   0.50    3.00    --  -90.00  39.00-120.00   84
 13  ω   -112.00  -1.00   0.50    3.00    --  -90.00  49.00-180.00  222
 14  ω   -174.00-144.00   0.50    3.00    --  -90.00  10.00 120.00   60
 15  ω    -43.00  -2.00   0.50    3.00    --  -90.00  10.00 120.00   82
 16  ω   -162.00  -2.00   0.50    3.00    --  -90.00  49.00 -60.00  320
 17  ω   -105.00 -22.00   0.50    3.00    --  -90.00  30.00   0.00  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_details 'Rigaku, AFC11 quarter χ goniometer'
_diffrn_measurement_device_type  
'Rigaku 007HF equipped with Varimax confocal mirrors and an AFC11 goniometer and HyPix 6000 detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0629723000
_diffrn_orient_matrix_UB_12      0.1704814000
_diffrn_orient_matrix_UB_13      0.0001031000
_diffrn_orient_matrix_UB_21      -0.0023405000
_diffrn_orient_matrix_UB_22      -0.0304395000
_diffrn_orient_matrix_UB_23      -0.0484909000
_diffrn_orient_matrix_UB_31      -0.0880123000
_diffrn_orient_matrix_UB_32      0.1226360000
_diffrn_orient_matrix_UB_33      -0.0121947000
_diffrn_radiation_collimation    'Varimax focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Rotating anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'Rigaku 007 HF'
_diffrn_source_voltage           40.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5663
_reflns_number_total             6140
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         6140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0263P)²+3.4647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1054
_refine_special_details          
'Hydrogen atoms H1 and H101 bonded to N1 and N101 respectively were located in the difference map and refined wit a riding model'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B),
 C12(H12A,H12B), C57(H57A,H57B), C58(H58A,H58B), C62(H62A,H62B), C61(H61A,H61B),
  C60(H60A,H60B), C59(H59A,H59B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C17(H17), C15(H15), C14(H14), C53(H53), C55(H55),
 C56(H56), C67(H67), C65(H65), C64(H64)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.20530(9) 0.17173(18) 0.72796(4) 0.0345(3) Uani 1 1 d . . . . .
O3 O 0.25372(10) 0.0336(2) 0.28040(4) 0.0298(3) Uani 1 1 d . . . . .
O1 O 0.12558(9) -0.1974(2) 0.42235(4) 0.0262(3) Uani 1 1 d . . . . .
O2 O 0.04134(8) -0.1503(2) 0.46970(4) 0.0264(3) Uani 1 1 d . . . . .
N2 N 0.31055(11) -0.1848(2) 0.44470(5) 0.0192(3) Uani 1 1 d . . . . .
H2 H 0.2647(15) -0.189(3) 0.4234(7) 0.023 Uiso 1 1 d . U . . .
N3 N 0.32830(10) -0.1593(2) 0.35896(5) 0.0186(3) Uani 1 1 d . . . . .
N1 N 0.11863(10) -0.1543(2) 0.45964(5) 0.0192(3) Uani 1 1 d . . . . .
N4 N 0.15301(11) 0.1573(2) 0.65568(5) 0.0225(3) Uani 1 1 d . . . . .
C1 C 0.29309(12) -0.1261(2) 0.48273(6) 0.0168(3) Uani 1 1 d . . . . .
C2 C 0.20211(12) -0.1094(2) 0.49168(6) 0.0175(4) Uani 1 1 d . . . . .
C3 C 0.18900(12) -0.0554(2) 0.53243(6) 0.0172(3) Uani 1 1 d . . . . .
H3 H 0.127014 -0.047511 0.537109 0.021 Uiso 1 1 calc R U . . .
C4 C 0.26426(12) -0.0132(2) 0.56609(6) 0.0170(4) Uani 1 1 d . . . . .
C5 C 0.35450(12) -0.0245(2) 0.55721(6) 0.0187(4) Uani 1 1 d . . . . .
H5 H 0.407396 0.007802 0.579376 0.022 Uiso 1 1 calc R U . . .
C6 C 0.36868(12) -0.0803(2) 0.51778(6) 0.0184(4) Uani 1 1 d . . . . .
H6 H 0.431149 -0.088623 0.513728 0.022 Uiso 1 1 calc R U . . .
C7 C 0.40404(12) -0.1890(3) 0.43582(6) 0.0207(4) Uani 1 1 d . . . . .
H7A H 0.445709 -0.268736 0.457215 0.025 Uiso 1 1 calc R U . . .
H7B H 0.431010 -0.063294 0.438073 0.025 Uiso 1 1 calc R U . . .
C8 C 0.39652(12) -0.2642(3) 0.39010(6) 0.0208(4) Uani 1 1 d . . . . .
H8A H 0.458640 -0.257075 0.382427 0.025 Uiso 1 1 calc R U . . .
H8B H 0.377293 -0.395223 0.389094 0.025 Uiso 1 1 calc R U . . .
C9 C 0.29403(13) -0.2578(3) 0.31817(6) 0.0234(4) Uani 1 1 d . . . . .
H9A H 0.267674 -0.378487 0.323941 0.028 Uiso 1 1 calc R U . . .
H9B H 0.346420 -0.279740 0.303527 0.028 Uiso 1 1 calc R U . . .
C10 C 0.21881(14) -0.1420(3) 0.28944(6) 0.0268(4) Uani 1 1 d . . . . .
H10A H 0.194692 -0.208040 0.261801 0.032 Uiso 1 1 calc R U . . .
H10B H 0.165825 -0.124713 0.303945 0.032 Uiso 1 1 calc R U . . .
C11 C 0.28967(14) 0.1293(3) 0.31998(6) 0.0263(4) Uani 1 1 d . . . . .
H11A H 0.237957 0.152898 0.334950 0.032 Uiso 1 1 calc R U . . .
H11B H 0.315301 0.249767 0.313489 0.032 Uiso 1 1 calc R U . . .
C12 C 0.36593(13) 0.0199(3) 0.34948(6) 0.0224(4) Uani 1 1 d . . . . .
H12A H 0.419276 0.001246 0.335274 0.027 Uiso 1 1 calc R U . . .
H12B H 0.389130 0.088408 0.376844 0.027 Uiso 1 1 calc R U . . .
C13 C 0.25152(12) 0.0364(2) 0.60994(6) 0.0178(4) Uani 1 1 d . . . . .
C17 C 0.16848(12) 0.1141(2) 0.61646(6) 0.0194(4) Uani 1 1 d . . . . .
H17 H 0.119773 0.137974 0.591680 0.023 Uiso 1 1 calc R U . . .
C16 C 0.22228(14) 0.1236(3) 0.68894(6) 0.0237(4) Uani 1 1 d . . . . .
C15 C 0.30842(14) 0.0484(3) 0.68785(6) 0.0236(4) Uani 1 1 d . . . . .
H15 H 0.355376 0.028012 0.713489 0.028 Uiso 1 1 calc R U . . .
C14 C 0.32231(13) 0.0043(3) 0.64718(6) 0.0216(4) Uani 1 1 d . . . . .
H14 H 0.380322 -0.048168 0.644396 0.026 Uiso 1 1 calc R U . . .
F51 F 0.51508(8) 0.63440(17) 0.72622(3) 0.0313(3) Uani 1 1 d . . . . .
O53 O -0.00674(10) 0.4665(2) 0.26729(4) 0.0292(3) Uani 1 1 d . . . . .
O51 O 0.29951(9) 0.3072(2) 0.41966(4) 0.0279(3) Uani 1 1 d . . . . .
O52 O 0.42842(8) 0.3458(2) 0.46793(4) 0.0260(3) Uani 1 1 d . . . . .
N52 N 0.13532(10) 0.3193(2) 0.44110(5) 0.0195(3) Uani 1 1 d . . . . .
H52 H 0.1623(15) 0.309(3) 0.4199(7) 0.023 Uiso 1 1 d . U . . .
N53 N 0.02901(10) 0.3116(2) 0.35276(5) 0.0200(3) Uani 1 1 d . . . . .
N51 N 0.34150(10) 0.3449(2) 0.45726(5) 0.0193(3) Uani 1 1 d . . . . .
N54 N 0.49671(10) 0.6335(2) 0.65379(5) 0.0216(3) Uani 1 1 d . . . . .
C51 C 0.18833(12) 0.3764(2) 0.47944(6) 0.0173(4) Uani 1 1 d . . . . .
C52 C 0.28806(12) 0.3900(2) 0.48914(6) 0.0172(4) Uani 1 1 d . . . . .
C53 C 0.33952(12) 0.4415(2) 0.53011(6) 0.0171(3) Uani 1 1 d . . . . .
H53 H 0.406126 0.445936 0.535264 0.020 Uiso 1 1 calc R U . . .
C54 C 0.29580(12) 0.4861(2) 0.56331(5) 0.0165(3) Uani 1 1 d . . . . .
C55 C 0.19708(12) 0.4791(2) 0.55391(6) 0.0185(4) Uani 1 1 d . . . . .
H55 H 0.164979 0.512539 0.575859 0.022 Uiso 1 1 calc R U . . .
C56 C 0.14560(12) 0.4254(2) 0.51403(6) 0.0183(4) Uani 1 1 d . . . . .
H56 H 0.079072 0.420973 0.509463 0.022 Uiso 1 1 calc R U . . .
C57 C 0.03335(12) 0.3149(3) 0.43185(6) 0.0220(4) Uani 1 1 d . . . . .
H57A H 0.008472 0.442019 0.431225 0.026 Uiso 1 1 calc R U . . .
H57B H 0.011948 0.245790 0.454901 0.026 Uiso 1 1 calc R U . . .
C58 C -0.00339(13) 0.2224(3) 0.38812(6) 0.0219(4) Uani 1 1 d . . . . .
H58A H 0.017143 0.092086 0.390004 0.026 Uiso 1 1 calc R U . . .
H58B H -0.072936 0.223826 0.381535 0.026 Uiso 1 1 calc R U . . .
C62 C 0.00692(15) 0.1975(3) 0.31367(6) 0.0273(4) Uani 1 1 d . . . . .
H62A H -0.061603 0.174534 0.305599 0.033 Uiso 1 1 calc R U . . .
H62B H 0.039119 0.077077 0.319541 0.033 Uiso 1 1 calc R U . . .
C61 C 0.03797(16) 0.2920(3) 0.27648(7) 0.0322(5) Uani 1 1 d . . . . .
H61A H 0.106961 0.309260 0.284043 0.039 Uiso 1 1 calc R U . . .
H61B H 0.022314 0.213192 0.250307 0.039 Uiso 1 1 calc R U . . .
C60 C 0.01580(14) 0.5797(3) 0.30491(6) 0.0271(4) Uani 1 1 d . . . . .
H60A H -0.015225 0.700899 0.298496 0.033 Uiso 1 1 calc R U . . .
H60B H 0.084530 0.600341 0.312744 0.033 Uiso 1 1 calc R U . . .
C59 C -0.01529(13) 0.4925(3) 0.34271(6) 0.0233(4) Uani 1 1 d . . . . .
H59A H 0.001990 0.573629 0.368432 0.028 Uiso 1 1 calc R U . . .
H59B H -0.084462 0.478304 0.335598 0.028 Uiso 1 1 calc R U . . .
C63 C 0.35081(12) 0.5332(2) 0.60742(6) 0.0177(4) Uani 1 1 d . . . . .
C67 C 0.44220(12) 0.5991(2) 0.61435(6) 0.0188(4) Uani 1 1 d . . . . .
H67 H 0.467875 0.621362 0.589689 0.023 Uiso 1 1 calc R U . . .
C66 C 0.45844(13) 0.6019(3) 0.68684(6) 0.0223(4) Uani 1 1 d . . . . .
C65 C 0.36848(14) 0.5422(3) 0.68520(6) 0.0238(4) Uani 1 1 d . . . . .
H65 H 0.344989 0.526281 0.710719 0.029 Uiso 1 1 calc R U . . .
C64 C 0.31386(13) 0.5063(3) 0.64433(6) 0.0206(4) Uani 1 1 d . . . . .
H64 H 0.251234 0.463464 0.641277 0.025 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 C16 1.356(2) . ?
O3 C10 1.425(2) . ?
O3 C11 1.425(2) . ?
O1 N1 1.2444(19) . ?
O2 N1 1.2379(19) . ?
N2 H2 0.84(2) . ?
N2 C1 1.351(2) . ?
N2 C7 1.452(2) . ?
N3 C8 1.451(2) . ?
N3 C9 1.462(2) . ?
N3 C12 1.468(2) . ?
N1 C2 1.439(2) . ?
N4 C17 1.345(2) . ?
N4 C16 1.310(2) . ?
C1 C2 1.422(2) . ?
C1 C6 1.419(2) . ?
C2 C3 1.399(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(2) . ?
C4 C5 1.408(2) . ?
C4 C13 1.482(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.369(2) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.525(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.515(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.510(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C17 1.392(2) . ?
C13 C14 1.403(3) . ?
C17 H17 0.9500 . ?
C16 C15 1.378(3) . ?
C15 H15 0.9500 . ?
C15 C14 1.382(3) . ?
C14 H14 0.9500 . ?
F51 C66 1.354(2) . ?
O53 C61 1.425(3) . ?
O53 C60 1.422(2) . ?
O51 N51 1.2408(19) . ?
O52 N51 1.2385(19) . ?
N52 H52 0.85(2) . ?
N52 C51 1.350(2) . ?
N52 C57 1.452(2) . ?
N53 C58 1.457(2) . ?
N53 C62 1.463(2) . ?
N53 C59 1.467(2) . ?
N51 C52 1.441(2) . ?
N54 C67 1.345(2) . ?
N54 C66 1.309(2) . ?
C51 C52 1.423(2) . ?
C51 C56 1.418(2) . ?
C52 C53 1.396(2) . ?
C53 H53 0.9500 . ?
C53 C54 1.381(2) . ?
C54 C55 1.406(2) . ?
C54 C63 1.487(2) . ?
C55 H55 0.9500 . ?
C55 C56 1.373(2) . ?
C56 H56 0.9500 . ?
C57 H57A 0.9900 . ?
C57 H57B 0.9900 . ?
C57 C58 1.523(2) . ?
C58 H58A 0.9900 . ?
C58 H58B 0.9900 . ?
C62 H62A 0.9900 . ?
C62 H62B 0.9900 . ?
C62 C61 1.514(3) . ?
C61 H61A 0.9900 . ?
C61 H61B 0.9900 . ?
C60 H60A 0.9900 . ?
C60 H60B 0.9900 . ?
C60 C59 1.507(3) . ?
C59 H59A 0.9900 . ?
C59 H59B 0.9900 . ?
C63 C67 1.388(2) . ?
C63 C64 1.402(2) . ?
C67 H67 0.9500 . ?
C66 C65 1.373(3) . ?
C65 H65 0.9500 . ?
C65 C64 1.384(3) . ?
C64 H64 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
C10 O3 C11 109.82(14) . . ?
C1 N2 H2 116.8(15) . . ?
C1 N2 C7 123.24(15) . . ?
C7 N2 H2 117.5(15) . . ?
C8 N3 C9 113.04(14) . . ?
C8 N3 C12 111.80(14) . . ?
C9 N3 C12 108.89(14) . . ?
O1 N1 C2 119.32(14) . . ?
O2 N1 O1 121.20(14) . . ?
O2 N1 C2 119.48(14) . . ?
C16 N4 C17 116.02(16) . . ?
N2 C1 C2 124.85(16) . . ?
N2 C1 C6 120.06(16) . . ?
C6 C1 C2 115.07(15) . . ?
C1 C2 N1 121.55(15) . . ?
C3 C2 N1 116.38(15) . . ?
C3 C2 C1 122.02(16) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.52(16) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 116.90(16) . . ?
C3 C4 C13 122.01(16) . . ?
C5 C4 C13 121.07(15) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 C4 122.32(16) . . ?
C6 C5 H5 118.8 . . ?
C1 C6 H6 118.9 . . ?
C5 C6 C1 122.14(16) . . ?
C5 C6 H6 118.9 . . ?
N2 C7 H7A 110.0 . . ?
N2 C7 H7B 110.0 . . ?
N2 C7 C8 108.43(14) . . ?
H7A C7 H7B 108.4 . . ?
C8 C7 H7A 110.0 . . ?
C8 C7 H7B 110.0 . . ?
N3 C8 C7 110.45(14) . . ?
N3 C8 H8A 109.6 . . ?
N3 C8 H8B 109.6 . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
N3 C9 H9A 110.0 . . ?
N3 C9 H9B 110.0 . . ?
N3 C9 C10 108.60(15) . . ?
H9A C9 H9B 108.4 . . ?
C10 C9 H9A 110.0 . . ?
C10 C9 H9B 110.0 . . ?
O3 C10 C9 111.86(16) . . ?
O3 C10 H10A 109.2 . . ?
O3 C10 H10B 109.2 . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
O3 C11 H11A 109.4 . . ?
O3 C11 H11B 109.4 . . ?
O3 C11 C12 111.32(16) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
N3 C12 C11 109.52(15) . . ?
N3 C12 H12A 109.8 . . ?
N3 C12 H12B 109.8 . . ?
C11 C12 H12A 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
C17 C13 C4 121.97(16) . . ?
C17 C13 C14 116.54(16) . . ?
C14 C13 C4 121.48(16) . . ?
N4 C17 C13 124.01(17) . . ?
N4 C17 H17 118.0 . . ?
C13 C17 H17 118.0 . . ?
F1 C16 C15 118.41(17) . . ?
N4 C16 F1 114.68(17) . . ?
N4 C16 C15 126.91(17) . . ?
C16 C15 H15 122.1 . . ?
C16 C15 C14 115.90(17) . . ?
C14 C15 H15 122.1 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.62(17) . . ?
C15 C14 H14 119.7 . . ?
C60 O53 C61 109.38(15) . . ?
C51 N52 H52 117.2(14) . . ?
C51 N52 C57 123.10(15) . . ?
C57 N52 H52 118.1(14) . . ?
C58 N53 C62 110.32(15) . . ?
C58 N53 C59 111.19(14) . . ?
C62 N53 C59 108.64(14) . . ?
O51 N51 C52 119.33(14) . . ?
O52 N51 O51 121.44(14) . . ?
O52 N51 C52 119.22(14) . . ?
C66 N54 C67 115.93(16) . . ?
N52 C51 C52 124.79(16) . . ?
N52 C51 C56 120.39(16) . . ?
C56 C51 C52 114.81(15) . . ?
C51 C52 N51 121.29(15) . . ?
C53 C52 N51 116.45(15) . . ?
C53 C52 C51 122.23(16) . . ?
C52 C53 H53 119.2 . . ?
C54 C53 C52 121.51(16) . . ?
C54 C53 H53 119.2 . . ?
C53 C54 C55 117.04(16) . . ?
C53 C54 C63 121.43(16) . . ?
C55 C54 C63 121.49(15) . . ?
C54 C55 H55 118.9 . . ?
C56 C55 C54 122.11(16) . . ?
C56 C55 H55 118.9 . . ?
C51 C56 H56 118.9 . . ?
C55 C56 C51 122.25(16) . . ?
C55 C56 H56 118.9 . . ?
N52 C57 H57A 109.8 . . ?
N52 C57 H57B 109.8 . . ?
N52 C57 C58 109.41(15) . . ?
H57A C57 H57B 108.2 . . ?
C58 C57 H57A 109.8 . . ?
C58 C57 H57B 109.8 . . ?
N53 C58 C57 112.99(15) . . ?
N53 C58 H58A 109.0 . . ?
N53 C58 H58B 109.0 . . ?
C57 C58 H58A 109.0 . . ?
C57 C58 H58B 109.0 . . ?
H58A C58 H58B 107.8 . . ?
N53 C62 H62A 109.5 . . ?
N53 C62 H62B 109.5 . . ?
N53 C62 C61 110.52(17) . . ?
H62A C62 H62B 108.1 . . ?
C61 C62 H62A 109.5 . . ?
C61 C62 H62B 109.5 . . ?
O53 C61 C62 111.04(16) . . ?
O53 C61 H61A 109.4 . . ?
O53 C61 H61B 109.4 . . ?
C62 C61 H61A 109.4 . . ?
C62 C61 H61B 109.4 . . ?
H61A C61 H61B 108.0 . . ?
O53 C60 H60A 109.3 . . ?
O53 C60 H60B 109.3 . . ?
O53 C60 C59 111.42(16) . . ?
H60A C60 H60B 108.0 . . ?
C59 C60 H60A 109.3 . . ?
C59 C60 H60B 109.3 . . ?
N53 C59 C60 110.60(16) . . ?
N53 C59 H59A 109.5 . . ?
N53 C59 H59B 109.5 . . ?
C60 C59 H59A 109.5 . . ?
C60 C59 H59B 109.5 . . ?
H59A C59 H59B 108.1 . . ?
C67 C63 C54 121.90(16) . . ?
C67 C63 C64 116.69(16) . . ?
C64 C63 C54 121.37(16) . . ?
N54 C67 C63 124.14(17) . . ?
N54 C67 H67 117.9 . . ?
C63 C67 H67 117.9 . . ?
F51 C66 C65 118.33(16) . . ?
N54 C66 F51 114.92(16) . . ?
N54 C66 C65 126.75(17) . . ?
C66 C65 H65 121.8 . . ?
C66 C65 C64 116.32(17) . . ?
C64 C65 H65 121.8 . . ?
C63 C64 H64 119.9 . . ?
C65 C64 C63 120.12(17) . . ?
C65 C64 H64 119.9 . . ?

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
F1 C16 C15 C14 -179.12(17) . . . . ?
O3 C11 C12 N3 -58.7(2) . . . . ?
O1 N1 C2 C1 -4.7(3) . . . . ?
O1 N1 C2 C3 177.66(16) . . . . ?
O2 N1 C2 C1 174.92(16) . . . . ?
O2 N1 C2 C3 -2.7(2) . . . . ?
N2 C1 C2 N1 -0.4(3) . . . . ?
N2 C1 C2 C3 177.14(17) . . . . ?
N2 C1 C6 C5 -178.43(17) . . . . ?
N2 C7 C8 N3 53.9(2) . . . . ?
N3 C9 C10 O3 59.4(2) . . . . ?
N1 C2 C3 C4 178.45(16) . . . . ?
N4 C16 C15 C14 0.0(3) . . . . ?
C1 N2 C7 C8 179.54(16) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C2 C3 C4 C13 -177.33(16) . . . . ?
C3 C4 C5 C6 -2.1(3) . . . . ?
C3 C4 C13 C17 -26.1(3) . . . . ?
C3 C4 C13 C14 152.79(18) . . . . ?
C4 C5 C6 C1 1.7(3) . . . . ?
C4 C13 C17 N4 178.40(16) . . . . ?
C4 C13 C14 C15 -178.77(17) . . . . ?
C5 C4 C13 C17 155.76(17) . . . . ?
C5 C4 C13 C14 -25.4(3) . . . . ?
C6 C1 C2 N1 -178.83(15) . . . . ?
C6 C1 C2 C3 -1.3(2) . . . . ?
C7 N2 C1 C2 175.96(17) . . . . ?
C7 N2 C1 C6 -5.6(3) . . . . ?
C8 N3 C9 C10 176.16(15) . . . . ?
C8 N3 C12 C11 -175.24(15) . . . . ?
C9 N3 C8 C7 -160.37(15) . . . . ?
C9 N3 C12 C11 59.14(19) . . . . ?
C10 O3 C11 C12 57.6(2) . . . . ?
C11 O3 C10 C9 -58.3(2) . . . . ?
C12 N3 C8 C7 76.32(18) . . . . ?
C12 N3 C9 C10 -58.94(19) . . . . ?
C13 C4 C5 C6 176.11(17) . . . . ?
C17 N4 C16 F1 178.82(16) . . . . ?
C17 N4 C16 C15 -0.3(3) . . . . ?
C17 C13 C14 C15 0.2(3) . . . . ?
C16 N4 C17 C13 0.6(3) . . . . ?
C16 C15 C14 C13 0.1(3) . . . . ?
C14 C13 C17 N4 -0.5(3) . . . . ?
F51 C66 C65 C64 -178.45(16) . . . . ?
O53 C60 C59 N53 58.5(2) . . . . ?
O51 N51 C52 C51 5.6(3) . . . . ?
O51 N51 C52 C53 -176.37(16) . . . . ?
O52 N51 C52 C51 -174.87(16) . . . . ?
O52 N51 C52 C53 3.1(2) . . . . ?
N52 C51 C52 N51 1.1(3) . . . . ?
N52 C51 C52 C53 -176.81(17) . . . . ?
N52 C51 C56 C55 178.09(17) . . . . ?
N52 C57 C58 N53 -56.7(2) . . . . ?
N53 C62 C61 O53 -58.9(2) . . . . ?
N51 C52 C53 C54 -179.42(16) . . . . ?
N54 C66 C65 C64 2.2(3) . . . . ?
C51 N52 C57 C58 -173.25(16) . . . . ?
C51 C52 C53 C54 -1.4(3) . . . . ?
C52 C51 C56 C55 -0.9(3) . . . . ?
C52 C53 C54 C55 -0.6(3) . . . . ?
C52 C53 C54 C63 177.36(16) . . . . ?
C53 C54 C55 C56 1.8(3) . . . . ?
C53 C54 C63 C67 23.6(3) . . . . ?
C53 C54 C63 C64 -153.94(18) . . . . ?
C54 C55 C56 C51 -1.1(3) . . . . ?
C54 C63 C67 N54 -175.98(16) . . . . ?
C54 C63 C64 C65 176.57(17) . . . . ?
C55 C54 C63 C67 -158.52(17) . . . . ?
C55 C54 C63 C64 23.9(3) . . . . ?
C56 C51 C52 N51 -179.98(16) . . . . ?
C56 C51 C52 C53 2.1(3) . . . . ?
C57 N52 C51 C52 -177.26(17) . . . . ?
C57 N52 C51 C56 3.9(3) . . . . ?
C58 N53 C62 C61 178.39(16) . . . . ?
C58 N53 C59 C60 -177.67(15) . . . . ?
C62 N53 C58 C57 169.10(15) . . . . ?
C62 N53 C59 C60 -56.1(2) . . . . ?
C61 O53 C60 C59 -59.1(2) . . . . ?
C60 O53 C61 C62 59.1(2) . . . . ?
C59 N53 C58 C57 -70.30(19) . . . . ?
C59 N53 C62 C61 56.3(2) . . . . ?
C63 C54 C55 C56 -176.12(17) . . . . ?
C67 N54 C66 F51 178.92(15) . . . . ?
C67 N54 C66 C65 -1.7(3) . . . . ?
C67 C63 C64 C65 -1.1(3) . . . . ?
C66 N54 C67 C63 -0.4(3) . . . . ?
C66 C65 C64 C63 -0.6(3) . . . . ?
C64 C63 C67 N54 1.7(3) . . . . ?

_olex2_date_sample_data_collection 2019-04-04
_olex2_date_sample_submission    2019-03-12
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id AKE-052
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.761
_oxdiff_exptl_absorpt_empirical_full_min 0.808
