# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_syl-06-08
_database_code_depnum_ccdc_archive 'CCDC 2281800'
loop_
_audit_author_name
_audit_author_address
'Tilo Soehnel'
;University of Auckland
New Zealand
;
_audit_update_record             
;
2023-07-16 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;
_audit_creation_date             2023-07-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C13 H13 N3 O)'
_chemical_formula_sum            'C26 H26 N6 O2'
_chemical_formula_weight         454.53
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H16 N4 O'
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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.45921(12)
_cell_length_b                   15.7500(3)
_cell_length_c                   21.1734(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2154.03(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7010
_cell_measurement_temperature    113(1)
_cell_measurement_theta_max      71.9270
_cell_measurement_theta_min      3.5110
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.781
_exptl_absorpt_coefficient_mu    0.743
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9625
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.521
_diffrn_reflns_theta_min         3.497
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      113(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -43.00  25.00   0.50    0.75    --  -47.23  38.00   0.00  136
  2  ω    -37.00 -12.00   0.50    3.00    --  -90.25  45.00 -30.00   50
  3  ω    -45.00 -12.00   0.50    3.00    --  -90.25  45.00 -60.00   66
  4  ω    -63.00 -22.00   0.50    0.75    --  -47.23  65.00   3.00   82
  5  ω    -37.00 -11.00   0.50    3.00    --  -90.25 111.00 -90.00   52
  6  ω    -61.00 -29.00   0.50    3.00    --  -90.25  65.00   3.00   64
  7  ω    -83.00 -54.00   0.50    3.00    --  -90.25 111.00 -90.00   58
  8  ω    -50.00 -19.00   0.50    3.00    --  -90.25  45.00-150.00   62
  9  ω    -95.00 -69.00   0.50    3.00    --  -90.25 -45.00 -30.00   52
 10  ω   -114.00 -75.00   0.50    0.75    --  -47.23-125.00 -60.00   78
 11  ω   -108.00 -78.00   0.50    0.75    --  -47.23-125.00 -90.00   60
 12  ω   -156.00-101.00   0.50    3.00    --  -90.25 -59.00  19.00  110
 13  ω   -116.00 -84.00   0.50    3.00    --  -90.25-108.00 145.00   64
 14  ω   -164.00-114.00   0.50    3.00    --  -90.25 -45.00 -30.00  100
 15  ω    -68.00 -16.00   0.50    3.00    --  -90.25  59.00 159.00  104
 16  ω     25.00  50.00   0.50    3.00    --   97.33 -65.00-131.00   50
 17  ω     22.00  47.00   0.50    3.00    --   97.33 -45.00 -90.00   50
 18  ω     20.00  45.00   0.50    3.00    --   97.33 -45.00-120.00   50
 19  ω     21.00  46.00   0.50    3.00    --   97.33 -45.00  60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2249889000
_diffrn_orient_matrix_UB_12      -0.0006245000
_diffrn_orient_matrix_UB_13      0.0240781000
_diffrn_orient_matrix_UB_21      0.0554462000
_diffrn_orient_matrix_UB_22      -0.0686088000
_diffrn_orient_matrix_UB_23      -0.0489849000
_diffrn_orient_matrix_UB_31      0.0564335000
_diffrn_orient_matrix_UB_32      0.0697226000
_diffrn_orient_matrix_UB_33      -0.0481087000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.644
_reflns_Friedel_fraction_full    0.902
_reflns_Friedel_fraction_max     0.829
_reflns_number_gt                3575
_reflns_number_total             3813
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 1345 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.18(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3813
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.078
_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)+(0.0558P)²+0.0967P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0926
_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
2.a Ternary CH refined with riding coordinates:
 C12(H12), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C13(H13A,H13B), C22(H22A,H22B), C23(H23A,H23B),
 C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C2(H2), C3(H3A), C4(H4), C5(H5), N4(H4A), N6(H6), C15(H15),
 C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 -0.7136(3) -0.41620(12) -0.21584(8) 0.0249(4) Uani 1 1 d . . . . .
N1 N -1.3553(3) -0.42623(13) 0.01746(10) 0.0190(4) Uani 1 1 d . . . . .
H1 H -1.472468 -0.452177 0.026260 0.023 Uiso 1 1 calc R U . . .
N2 N -1.2068(3) -0.44272(12) -0.15131(9) 0.0185(4) Uani 1 1 d . . . . .
N3 N -1.0363(4) -0.46735(13) -0.24255(10) 0.0224(5) Uani 1 1 d . . . . .
H3 H -1.019400 -0.471085 -0.283699 0.027 Uiso 1 1 calc R U . . .
C1 C -1.2400(4) -0.37770(14) 0.05894(11) 0.0179(5) Uani 1 1 d . . . . .
C2 C -1.2765(4) -0.35782(15) 0.12200(12) 0.0214(5) Uani 1 1 d . . . . .
H2 H -1.393068 -0.379786 0.143933 0.026 Uiso 1 1 calc R U . . .
C3 C -1.1360(4) -0.30485(16) 0.15131(12) 0.0232(6) Uani 1 1 d . . . . .
H3A H -1.157057 -0.289938 0.194311 0.028 Uiso 1 1 calc R U . . .
C4 C -0.9636(4) -0.27250(16) 0.11940(13) 0.0243(6) Uani 1 1 d . . . . .
H4 H -0.871381 -0.235469 0.140933 0.029 Uiso 1 1 calc R U . . .
C5 C -0.9249(4) -0.29344(15) 0.05715(12) 0.0218(5) Uani 1 1 d . . . . .
H5 H -0.806282 -0.272050 0.035918 0.026 Uiso 1 1 calc R U . . .
C6 C -1.0652(4) -0.34707(14) 0.02608(11) 0.0172(5) Uani 1 1 d . . . . .
C7 C -1.0784(4) -0.38006(14) -0.03725(11) 0.0172(5) Uani 1 1 d . . . . .
C8 C -1.2547(4) -0.42702(14) -0.04042(11) 0.0182(5) Uani 1 1 d . . . . .
C9 C -1.3322(4) -0.47209(16) -0.09830(12) 0.0203(5) Uani 1 1 d . . . . .
H9A H -1.318093 -0.534297 -0.093152 0.024 Uiso 1 1 calc R U . . .
H9B H -1.479981 -0.458605 -0.105602 0.024 Uiso 1 1 calc R U . . .
C10 C -1.2251(4) -0.49199(16) -0.20979(12) 0.0231(6) Uani 1 1 d . . . . .
H10A H -1.228310 -0.553766 -0.201219 0.028 Uiso 1 1 calc R U . . .
H10B H -1.350009 -0.475768 -0.234031 0.028 Uiso 1 1 calc R U . . .
C11 C -0.8918(4) -0.43847(15) -0.20300(11) 0.0196(5) Uani 1 1 d . . . . .
C12 C -0.9846(4) -0.44019(15) -0.13756(12) 0.0177(5) Uani 1 1 d . . . . .
H12 H -0.945077 -0.495000 -0.116999 0.021 Uiso 1 1 calc R U . . .
C13 C -0.9351(4) -0.36861(15) -0.09231(11) 0.0197(5) Uani 1 1 d . . . . .
H13A H -0.788918 -0.371832 -0.078421 0.024 Uiso 1 1 calc R U . . .
H13B H -0.958515 -0.312884 -0.112725 0.024 Uiso 1 1 calc R U . . .
O2 O -0.1153(3) -0.98331(11) -0.11456(8) 0.0232(4) Uani 1 1 d . . . . .
N4 N -0.7001(3) -0.78502(12) 0.08381(9) 0.0177(4) Uani 1 1 d . . . . .
H4A H -0.821311 -0.759557 0.083026 0.021 Uiso 1 1 calc R U . . .
N5 N -0.5309(3) -0.85583(12) -0.07259(9) 0.0147(4) Uani 1 1 d . . . . .
N6 N -0.4056(3) -0.92224(13) -0.15862(9) 0.0186(4) Uani 1 1 d . . . . .
H6 H -0.373358 -0.928699 -0.198717 0.022 Uiso 1 1 calc R U . . .
C14 C -0.5675(4) -0.78886(14) 0.13492(11) 0.0180(5) Uani 1 1 d . . . . .
C15 C -0.5895(4) -0.75570(15) 0.19593(12) 0.0222(6) Uani 1 1 d . . . . .
H15 H -0.707147 -0.723010 0.207518 0.027 Uiso 1 1 calc R U . . .
C16 C -0.4334(5) -0.77251(16) 0.23837(12) 0.0247(6) Uani 1 1 d . . . . .
H16 H -0.444530 -0.750784 0.280086 0.030 Uiso 1 1 calc R U . . .
C17 C -0.2587(5) -0.82055(16) 0.22220(12) 0.0233(6) Uani 1 1 d . . . . .
H17 H -0.154933 -0.831373 0.252950 0.028 Uiso 1 1 calc R U . . .
C18 C -0.2367(4) -0.85236(15) 0.16149(11) 0.0202(5) Uani 1 1 d . . . . .
H18 H -0.117781 -0.884461 0.150204 0.024 Uiso 1 1 calc R U . . .
C19 C -0.3921(4) -0.83643(13) 0.11723(11) 0.0162(5) Uani 1 1 d . . . . .
C20 C -0.4228(4) -0.86036(13) 0.05216(11) 0.0145(5) Uani 1 1 d . . . . .
C21 C -0.6099(4) -0.82783(13) 0.03436(11) 0.0150(5) Uani 1 1 d . . . . .
C22 C -0.7032(4) -0.83850(15) -0.02963(11) 0.0172(5) Uani 1 1 d . . . . .
H22A H -0.802726 -0.886317 -0.029755 0.021 Uiso 1 1 calc R U . . .
H22B H -0.776971 -0.786178 -0.042489 0.021 Uiso 1 1 calc R U . . .
C23 C -0.5931(4) -0.88102(15) -0.13674(11) 0.0181(5) Uani 1 1 d . . . . .
H23A H -0.711783 -0.920788 -0.136035 0.022 Uiso 1 1 calc R U . . .
H23B H -0.628444 -0.831119 -0.163041 0.022 Uiso 1 1 calc R U . . .
C24 C -0.2874(4) -0.94932(14) -0.11082(12) 0.0166(5) Uani 1 1 d . . . . .
C25 C -0.4053(4) -0.92887(14) -0.05087(11) 0.0148(5) Uani 1 1 d . . . . .
H25 H -0.499962 -0.977268 -0.040884 0.018 Uiso 1 1 calc R U . . .
C26 C -0.2811(4) -0.90701(15) 0.00785(10) 0.0167(5) Uani 1 1 d . . . . .
H26A H -0.228751 -0.959448 0.028094 0.020 Uiso 1 1 calc R U . . .
H26B H -0.161267 -0.870862 -0.003431 0.020 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 C11 1.234(3) . ?
N1 H1 0.8800 . ?
N1 C1 1.382(3) . ?
N1 C8 1.387(3) . ?
N2 C9 1.460(3) . ?
N2 C10 1.466(3) . ?
N2 C12 1.464(3) . ?
N3 H3 0.8800 . ?
N3 C10 1.456(3) . ?
N3 C11 1.334(3) . ?
C1 C2 1.392(3) . ?
C1 C6 1.411(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(4) . ?
C3 H3A 0.9500 . ?
C3 C4 1.399(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.382(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.402(3) . ?
C6 C7 1.441(3) . ?
C7 C8 1.360(4) . ?
C7 C13 1.500(3) . ?
C8 C9 1.502(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.510(3) . ?
C12 H12 1.0000 . ?
C12 C13 1.514(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
O2 C24 1.236(3) . ?
N4 H4A 0.8800 . ?
N4 C14 1.381(3) . ?
N4 C21 1.375(3) . ?
N5 C22 1.463(3) . ?
N5 C23 1.471(3) . ?
N5 C25 1.481(3) . ?
N6 H6 0.8800 . ?
N6 C23 1.450(3) . ?
N6 C24 1.338(3) . ?
C14 C15 1.401(3) . ?
C14 C19 1.409(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.376(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.401(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.387(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.396(4) . ?
C19 C20 1.442(3) . ?
C20 C21 1.366(3) . ?
C20 C26 1.503(3) . ?
C21 C22 1.493(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.515(3) . ?
C25 H25 1.0000 . ?
C25 C26 1.519(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 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
C1 N1 H1 125.9 . . ?
C1 N1 C8 108.3(2) . . ?
C8 N1 H1 125.9 . . ?
C9 N2 C10 115.9(2) . . ?
C9 N2 C12 113.55(19) . . ?
C12 N2 C10 105.2(2) . . ?
C10 N3 H3 123.9 . . ?
C11 N3 H3 123.9 . . ?
C11 N3 C10 112.2(2) . . ?
N1 C1 C2 130.0(2) . . ?
N1 C1 C6 107.9(2) . . ?
C2 C1 C6 122.1(2) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 C1 117.1(2) . . ?
C3 C2 H2 121.4 . . ?
C2 C3 H3A 119.1 . . ?
C2 C3 C4 121.8(2) . . ?
C4 C3 H3A 119.1 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.2(2) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.3(2) . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C7 106.7(2) . . ?
C5 C6 C1 119.4(2) . . ?
C5 C6 C7 133.8(2) . . ?
C6 C7 C13 130.1(2) . . ?
C8 C7 C6 107.0(2) . . ?
C8 C7 C13 123.0(2) . . ?
N1 C8 C9 124.7(2) . . ?
C7 C8 N1 110.1(2) . . ?
C7 C8 C9 125.2(2) . . ?
N2 C9 C8 107.0(2) . . ?
N2 C9 H9A 110.3 . . ?
N2 C9 H9B 110.3 . . ?
C8 C9 H9A 110.3 . . ?
C8 C9 H9B 110.3 . . ?
H9A C9 H9B 108.6 . . ?
N2 C10 H10A 111.5 . . ?
N2 C10 H10B 111.5 . . ?
N3 C10 N2 101.2(2) . . ?
N3 C10 H10A 111.5 . . ?
N3 C10 H10B 111.5 . . ?
H10A C10 H10B 109.4 . . ?
O1 C11 N3 127.7(2) . . ?
O1 C11 C12 125.3(2) . . ?
N3 C11 C12 107.0(2) . . ?
N2 C12 C11 101.9(2) . . ?
N2 C12 H12 108.3 . . ?
N2 C12 C13 110.7(2) . . ?
C11 C12 H12 108.3 . . ?
C11 C12 C13 118.9(2) . . ?
C13 C12 H12 108.3 . . ?
C7 C13 C12 105.8(2) . . ?
C7 C13 H13A 110.6 . . ?
C7 C13 H13B 110.6 . . ?
C12 C13 H13A 110.6 . . ?
C12 C13 H13B 110.6 . . ?
H13A C13 H13B 108.7 . . ?
C14 N4 H4A 125.9 . . ?
C21 N4 H4A 125.9 . . ?
C21 N4 C14 108.2(2) . . ?
C22 N5 C23 114.63(19) . . ?
C22 N5 C25 111.64(18) . . ?
C23 N5 C25 103.10(17) . . ?
C23 N6 H6 123.9 . . ?
C24 N6 H6 123.9 . . ?
C24 N6 C23 112.19(19) . . ?
N4 C14 C15 130.1(2) . . ?
N4 C14 C19 108.3(2) . . ?
C15 C14 C19 121.7(2) . . ?
C14 C15 H15 121.4 . . ?
C16 C15 C14 117.1(2) . . ?
C16 C15 H15 121.4 . . ?
C15 C16 H16 118.8 . . ?
C15 C16 C17 122.3(2) . . ?
C17 C16 H16 118.8 . . ?
C16 C17 H17 119.9 . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.6 . . ?
C17 C18 C19 118.9(2) . . ?
C19 C18 H18 120.6 . . ?
C14 C19 C20 106.4(2) . . ?
C18 C19 C14 119.7(2) . . ?
C18 C19 C20 133.9(2) . . ?
C19 C20 C26 129.9(2) . . ?
C21 C20 C19 106.7(2) . . ?
C21 C20 C26 123.4(2) . . ?
N4 C21 C22 125.1(2) . . ?
C20 C21 N4 110.4(2) . . ?
C20 C21 C22 124.5(2) . . ?
N5 C22 C21 106.2(2) . . ?
N5 C22 H22A 110.5 . . ?
N5 C22 H22B 110.5 . . ?
C21 C22 H22A 110.5 . . ?
C21 C22 H22B 110.5 . . ?
H22A C22 H22B 108.7 . . ?
N5 C23 H23A 111.6 . . ?
N5 C23 H23B 111.6 . . ?
N6 C23 N5 100.83(19) . . ?
N6 C23 H23A 111.6 . . ?
N6 C23 H23B 111.6 . . ?
H23A C23 H23B 109.4 . . ?
O2 C24 N6 127.1(2) . . ?
O2 C24 C25 126.7(2) . . ?
N6 C24 C25 106.2(2) . . ?
N5 C25 C24 100.40(17) . . ?
N5 C25 H25 108.8 . . ?
N5 C25 C26 111.56(18) . . ?
C24 C25 H25 108.8 . . ?
C24 C25 C26 117.9(2) . . ?
C26 C25 H25 108.8 . . ?
C20 C26 C25 107.5(2) . . ?
C20 C26 H26A 110.2 . . ?
C20 C26 H26B 110.2 . . ?
C25 C26 H26A 110.2 . . ?
C25 C26 H26B 110.2 . . ?
H26A C26 H26B 108.5 . . ?

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 C11 C12 N2 161.8(2) . . . . ?
O1 C11 C12 C13 39.8(4) . . . . ?
N1 C1 C2 C3 -177.8(2) . . . . ?
N1 C1 C6 C5 178.0(2) . . . . ?
N1 C1 C6 C7 -0.6(2) . . . . ?
N1 C8 C9 N2 168.3(2) . . . . ?
N2 C12 C13 C7 52.4(2) . . . . ?
N3 C11 C12 N2 -19.9(2) . . . . ?
N3 C11 C12 C13 -141.8(2) . . . . ?
C1 N1 C8 C7 -0.2(3) . . . . ?
C1 N1 C8 C9 -179.2(2) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C1 C6 C7 C8 0.5(2) . . . . ?
C1 C6 C7 C13 -179.6(2) . . . . ?
C2 C1 C6 C5 -1.3(3) . . . . ?
C2 C1 C6 C7 -179.9(2) . . . . ?
C2 C3 C4 C5 -1.0(4) . . . . ?
C3 C4 C5 C6 1.1(4) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C4 C5 C6 C7 178.2(2) . . . . ?
C5 C6 C7 C8 -177.9(3) . . . . ?
C5 C6 C7 C13 2.0(4) . . . . ?
C6 C1 C2 C3 1.4(4) . . . . ?
C6 C7 C8 N1 -0.2(3) . . . . ?
C6 C7 C8 C9 178.8(2) . . . . ?
C6 C7 C13 C12 160.7(2) . . . . ?
C7 C8 C9 N2 -10.6(3) . . . . ?
C8 N1 C1 C2 179.8(2) . . . . ?
C8 N1 C1 C6 0.5(3) . . . . ?
C8 C7 C13 C12 -19.4(3) . . . . ?
C9 N2 C10 N3 -160.4(2) . . . . ?
C9 N2 C12 C11 161.21(19) . . . . ?
C9 N2 C12 C13 -71.3(2) . . . . ?
C10 N2 C9 C8 167.1(2) . . . . ?
C10 N2 C12 C11 33.5(2) . . . . ?
C10 N2 C12 C13 160.93(19) . . . . ?
C10 N3 C11 O1 176.7(2) . . . . ?
C10 N3 C11 C12 -1.6(3) . . . . ?
C11 N3 C10 N2 22.3(3) . . . . ?
C11 C12 C13 C7 169.9(2) . . . . ?
C12 N2 C9 C8 45.1(3) . . . . ?
C12 N2 C10 N3 -34.1(2) . . . . ?
C13 C7 C8 N1 179.9(2) . . . . ?
C13 C7 C8 C9 -1.0(4) . . . . ?
O2 C24 C25 N5 152.8(2) . . . . ?
O2 C24 C25 C26 31.4(3) . . . . ?
N4 C14 C15 C16 177.5(2) . . . . ?
N4 C14 C19 C18 -177.8(2) . . . . ?
N4 C14 C19 C20 0.9(2) . . . . ?
N4 C21 C22 N5 157.8(2) . . . . ?
N5 C25 C26 C20 44.7(2) . . . . ?
N6 C24 C25 N5 -26.4(2) . . . . ?
N6 C24 C25 C26 -147.8(2) . . . . ?
C14 N4 C21 C20 0.7(3) . . . . ?
C14 N4 C21 C22 180.0(2) . . . . ?
C14 C15 C16 C17 0.0(4) . . . . ?
C14 C19 C20 C21 -0.5(2) . . . . ?
C14 C19 C20 C26 176.1(2) . . . . ?
C15 C14 C19 C18 0.9(3) . . . . ?
C15 C14 C19 C20 179.6(2) . . . . ?
C15 C16 C17 C18 0.7(4) . . . . ?
C16 C17 C18 C19 -0.7(4) . . . . ?
C17 C18 C19 C14 -0.2(3) . . . . ?
C17 C18 C19 C20 -178.4(2) . . . . ?
C18 C19 C20 C21 177.9(2) . . . . ?
C18 C19 C20 C26 -5.5(4) . . . . ?
C19 C14 C15 C16 -0.9(4) . . . . ?
C19 C20 C21 N4 -0.1(2) . . . . ?
C19 C20 C21 C22 -179.4(2) . . . . ?
C19 C20 C26 C25 170.0(2) . . . . ?
C20 C21 C22 N5 -23.0(3) . . . . ?
C21 N4 C14 C15 -179.5(2) . . . . ?
C21 N4 C14 C19 -1.0(2) . . . . ?
C21 C20 C26 C25 -13.9(3) . . . . ?
C22 N5 C23 N6 -160.03(19) . . . . ?
C22 N5 C25 C24 163.46(18) . . . . ?
C22 N5 C25 C26 -70.8(2) . . . . ?
C23 N5 C22 C21 171.27(18) . . . . ?
C23 N5 C25 C24 39.9(2) . . . . ?
C23 N5 C25 C26 165.70(19) . . . . ?
C23 N6 C24 O2 -176.7(2) . . . . ?
C23 N6 C24 C25 2.5(3) . . . . ?
C24 N6 C23 N5 22.6(2) . . . . ?
C24 C25 C26 C20 160.17(18) . . . . ?
C25 N5 C22 C21 54.5(2) . . . . ?
C25 N5 C23 N6 -38.5(2) . . . . ?
C26 C20 C21 N4 -177.0(2) . . . . ?
C26 C20 C21 C22 3.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.955
_oxdiff_exptl_absorpt_empirical_full_min 0.540
####################################################################### 
# 
# 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_syl-06-23_2
_database_code_depnum_ccdc_archive 'CCDC 2281802'
loop_
_audit_author_name
_audit_author_address
'Tilo Soehnel'
;University of Auckland
New Zealand
;
_audit_update_record             
;
2023-07-16 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;
_audit_creation_date             2023-07-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl, C12 H14 N3 O, H O0.5'
_chemical_formula_sum            'C12 H15 Cl N3 O1.50'
_chemical_formula_weight         260.72
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H14 N4 O2'
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'
Cl Cl 0.3639 0.7018 '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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   12.4988(3)
_cell_length_b                   7.09306(15)
_cell_length_c                   13.9973(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.543(2)
_cell_angle_gamma                90
_cell_volume                     1211.31(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3630
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      71.6460
_cell_measurement_theta_min      6.4680
_shelx_estimated_absorpt_T_max   0.898
_shelx_estimated_absorpt_T_min   0.447
_exptl_absorpt_coefficient_mu    2.742
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             548
_exptl_crystal_recrystallization_method EtOH/MeOH
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4201
_diffrn_reflns_point_group_measured_fraction_full 0.842
_diffrn_reflns_point_group_measured_fraction_max 0.799
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.156
_diffrn_reflns_theta_min         3.235
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     15.00  47.00   0.50    0.33    --   47.23 -83.00  74.00   64
  2  ω      1.00  27.00   0.50    0.33    --   47.23 -19.00 120.00   52
  3  ω     25.00  71.50   0.50    1.33    --   97.33 -61.00 150.00   93
  4  ω     73.00  99.00   0.50    1.33    --   97.33 -83.00  74.00   52
  5  ω     46.00 106.00   0.50    1.33    --   97.33 -77.00 -90.00  120
  6  ω     24.00  50.50   0.50    1.33    --   97.33 -45.00-150.00   53
  7  ω     20.00  46.50   0.50    1.33    --   97.33 -45.00-120.00   53
  8  ω     20.00  50.50   0.50    1.33    --   97.33 -45.00 -60.00   61
  9  ω     -1.00  37.00   0.50    0.33    --   47.23 -99.00-150.00   76
 10  ω     22.00  50.00   0.50    1.33    --   97.33 -45.00  60.00   56
 11  ω     21.00  51.00   0.50    1.33    --   97.33 -45.00 150.00   60
 12  ω    -33.00  -1.00   0.50    0.33    --   47.23 -19.00 120.00   64
 13  ω    -40.00   0.00   0.50    0.33    --  -47.23  38.00 120.00   80
 14  ω    -68.00 -28.00   0.50    1.33    --  -90.25  61.00 120.00   80
 15  ω    -66.00 -19.50   0.50    1.33    --  -90.25  61.00  30.00   93
 16  ω    -83.00 -33.00   0.50    1.33    --  -90.25 111.00 120.00  100
 17  ω     -2.00  26.00   0.50    0.33    --  -47.23  83.00-164.00   56
 18  ω    -37.00  -9.00   0.50    0.33    --  -47.23  83.00-164.00   56
 19  ω    -41.00 -14.50   0.50    1.33    --  -90.25 111.00-150.00   53
 20  ω    -66.00 -40.00   0.50    1.33    --  -90.25  83.00-164.00   52
 21  ω    -51.00 -15.00   0.50    1.33    --  -90.25  45.00-150.00   72
 22  ω    -78.00 -47.50   0.50    1.33    --  -90.25 111.00-150.00   61
 23  ω   -157.00 -81.00   0.50    1.33    --  -90.25 -83.00  74.00  152
 24  ω   -153.00 -83.50   0.50    1.33    --  -90.25 -95.00   0.00  139
 25  ω   -112.00 -73.50   0.50    0.33    --  -47.23-125.00-120.00   77
 26  ω    109.00 135.00   0.50    1.33    --   97.33  83.00-164.00   52
 27  ω     67.00 129.00   0.50    1.33    --   97.33 178.00-150.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0995991000
_diffrn_orient_matrix_UB_12      0.1332182000
_diffrn_orient_matrix_UB_13      0.0231810000
_diffrn_orient_matrix_UB_21      0.0644034000
_diffrn_orient_matrix_UB_22      -0.1349865000
_diffrn_orient_matrix_UB_23      -0.0530193000
_diffrn_orient_matrix_UB_31      -0.0433640000
_diffrn_orient_matrix_UB_32      0.1058443000
_diffrn_orient_matrix_UB_33      -0.0967520000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.540
_reflns_Friedel_fraction_full    0.657
_reflns_Friedel_fraction_max     0.613
_reflns_number_gt                1875
_reflns_number_total             1911
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 645 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         1911
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0281
_refine_ls_restrained_S_all      1.072
_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)+(0.0389P)²+0.6219P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0739
_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, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O2-H2C
 0.85 with sigma of 0.02
3.a Free rotating group:
 O2(H2C)
3.b Ternary CH refined with riding coordinates:
 C9(H9)
3.c Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), C8(H8A,H8B), C11(H11A,H11B)
3.d Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5)
3.e X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.09333(4) 0.32127(9) -0.14258(4) 0.02109(17) Uani 1 1 d . . . . .
O1 O -0.10704(15) -0.0377(3) -0.09420(13) 0.0219(4) Uani 1 1 d . . . . .
N1 N 0.32884(15) -0.1572(4) -0.22714(14) 0.0177(5) Uani 1 1 d . . . . .
H1 H 0.391147 -0.183195 -0.186255 0.021 Uiso 1 1 calc R U . . .
N2 N 0.09587(16) -0.1135(3) -0.10485(14) 0.0168(5) Uani 1 1 d . . . . .
H2A H 0.099057 0.014518 -0.107678 0.020 Uiso 1 1 calc R U . . .
H2B H 0.077034 -0.145087 -0.047673 0.020 Uiso 1 1 calc R U . . .
N3 N -0.18954(16) -0.1810(4) -0.23447(15) 0.0228(5) Uani 1 1 d . . . . .
H3A H -0.255551 -0.151059 -0.227000 0.027 Uiso 1 1 calc R U . . .
H3B H -0.181569 -0.245908 -0.286063 0.027 Uiso 1 1 calc R U . . .
C1 C 0.3168(2) -0.1084(4) -0.32462(18) 0.0179(5) Uani 1 1 d . . . . .
C2 C 0.3954(2) -0.0836(4) -0.3805(2) 0.0216(6) Uani 1 1 d . . . . .
H2 H 0.471228 -0.101407 -0.353195 0.026 Uiso 1 1 calc R U . . .
C3 C 0.3585(2) -0.0318(5) -0.4775(2) 0.0247(6) Uani 1 1 d . . . . .
H3 H 0.409983 -0.015739 -0.517743 0.030 Uiso 1 1 calc R U . . .
C4 C 0.2468(2) -0.0025(4) -0.51762(19) 0.0234(6) Uani 1 1 d . . . . .
H4 H 0.224212 0.034025 -0.584252 0.028 Uiso 1 1 calc R U . . .
C5 C 0.1695(2) -0.0259(4) -0.46217(19) 0.0198(6) Uani 1 1 d . . . . .
H5 H 0.094076 -0.005976 -0.490131 0.024 Uiso 1 1 calc R U . . .
C6 C 0.2034(2) -0.0795(4) -0.36389(18) 0.0164(5) Uani 1 1 d . . . . .
C7 C 0.1484(2) -0.1145(4) -0.28585(17) 0.0167(5) Uani 1 1 d . . . . .
C8 C 0.0283(2) -0.1015(4) -0.28580(17) 0.0169(5) Uani 1 1 d . . . . .
H8A H -0.014841 -0.173012 -0.341886 0.020 Uiso 1 1 calc R U . . .
H8B H 0.004326 0.031761 -0.292356 0.020 Uiso 1 1 calc R U . . .
C9 C 0.00879(17) -0.1836(5) -0.18915(15) 0.0156(5) Uani 1 1 d . . . . .
H9 H 0.013207 -0.324239 -0.191870 0.019 Uiso 1 1 calc R U . . .
C10 C -0.1020(2) -0.1284(4) -0.16792(17) 0.0170(5) Uani 1 1 d . . . . .
C11 C 0.20677(18) -0.1931(5) -0.10527(16) 0.0177(5) Uani 1 1 d . . . . .
H11A H 0.263587 -0.130238 -0.055079 0.021 Uiso 1 1 calc R U . . .
H11B H 0.208480 -0.330008 -0.091177 0.021 Uiso 1 1 calc R U . . .
C12 C 0.22677(18) -0.1581(4) -0.20500(16) 0.0165(5) Uani 1 1 d . . . . .
O2 O 0.500000 0.0769(5) 0.000000 0.0380(8) Uani 1 2 d DGS T P . .
H2C H 0.525660 -0.000758 -0.035471 0.057 Uiso 1 1 d DG 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 C10 1.229(3) . ?
N1 H1 0.8800 . ?
N1 C1 1.384(3) . ?
N1 C12 1.377(3) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 C9 1.506(3) . ?
N2 C11 1.498(3) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N3 C10 1.328(3) . ?
C1 C2 1.394(4) . ?
C1 C6 1.419(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.402(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.374(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.401(4) . ?
C6 C7 1.433(4) . ?
C7 C8 1.504(3) . ?
C7 C12 1.362(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.540(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.529(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.491(3) . ?
O2 H2C 0.85(5) 2_655 ?
O2 H2C 0.8499 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1 125.8 . . ?
C12 N1 H1 125.8 . . ?
C12 N1 C1 108.38(18) . . ?
H2A N2 H2B 107.8 . . ?
C9 N2 H2A 109.1 . . ?
C9 N2 H2B 109.1 . . ?
C11 N2 H2A 109.1 . . ?
C11 N2 H2B 109.1 . . ?
C11 N2 C9 112.6(2) . . ?
H3A N3 H3B 120.0 . . ?
C10 N3 H3A 120.0 . . ?
C10 N3 H3B 120.0 . . ?
N1 C1 C2 130.2(2) . . ?
N1 C1 C6 107.7(2) . . ?
C2 C1 C6 122.1(2) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 C1 117.2(2) . . ?
C3 C2 H2 121.4 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.5(3) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.2(2) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C7 106.5(2) . . ?
C5 C6 C1 118.9(2) . . ?
C5 C6 C7 134.6(2) . . ?
C6 C7 C8 129.4(2) . . ?
C12 C7 C6 107.2(2) . . ?
C12 C7 C8 123.5(2) . . ?
C7 C8 H8A 109.9 . . ?
C7 C8 H8B 109.9 . . ?
C7 C8 C9 109.01(19) . . ?
H8A C8 H8B 108.3 . . ?
C9 C8 H8A 109.9 . . ?
C9 C8 H8B 109.9 . . ?
N2 C9 C8 109.8(2) . . ?
N2 C9 H9 108.8 . . ?
N2 C9 C10 107.1(2) . . ?
C8 C9 H9 108.8 . . ?
C10 C9 C8 113.4(2) . . ?
C10 C9 H9 108.8 . . ?
O1 C10 N3 123.5(2) . . ?
O1 C10 C9 120.8(2) . . ?
N3 C10 C9 115.8(2) . . ?
N2 C11 H11A 110.4 . . ?
N2 C11 H11B 110.4 . . ?
H11A C11 H11B 108.6 . . ?
C12 C11 N2 106.50(19) . . ?
C12 C11 H11A 110.4 . . ?
C12 C11 H11B 110.4 . . ?
N1 C12 C11 124.28(19) . . ?
C7 C12 N1 110.3(2) . . ?
C7 C12 C11 125.4(2) . . ?
H2C O2 H2C 99.1 . 2_655 ?

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
N1 C1 C2 C3 -179.3(3) . . . . ?
N1 C1 C6 C5 179.2(2) . . . . ?
N1 C1 C6 C7 -0.4(3) . . . . ?
N2 C9 C10 O1 2.1(4) . . . . ?
N2 C9 C10 N3 -179.2(2) . . . . ?
N2 C11 C12 N1 159.6(3) . . . . ?
N2 C11 C12 C7 -17.3(4) . . . . ?
C1 N1 C12 C7 1.1(3) . . . . ?
C1 N1 C12 C11 -176.2(3) . . . . ?
C1 C2 C3 C4 1.0(5) . . . . ?
C1 C6 C7 C8 178.9(3) . . . . ?
C1 C6 C7 C12 1.0(3) . . . . ?
C2 C1 C6 C5 0.6(4) . . . . ?
C2 C1 C6 C7 -179.0(3) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C4 C5 C6 C7 179.3(3) . . . . ?
C5 C6 C7 C8 -0.6(5) . . . . ?
C5 C6 C7 C12 -178.5(3) . . . . ?
C6 C1 C2 C3 -1.0(4) . . . . ?
C6 C7 C8 C9 171.0(3) . . . . ?
C6 C7 C12 N1 -1.3(3) . . . . ?
C6 C7 C12 C11 176.0(3) . . . . ?
C7 C8 C9 N2 43.9(3) . . . . ?
C7 C8 C9 C10 163.6(2) . . . . ?
C8 C7 C12 N1 -179.3(3) . . . . ?
C8 C7 C12 C11 -2.0(4) . . . . ?
C8 C9 C10 O1 -119.1(3) . . . . ?
C8 C9 C10 N3 59.6(3) . . . . ?
C9 N2 C11 C12 51.7(3) . . . . ?
C11 N2 C9 C8 -68.8(3) . . . . ?
C11 N2 C9 C10 167.7(2) . . . . ?
C12 N1 C1 C2 178.1(3) . . . . ?
C12 N1 C1 C6 -0.4(3) . . . . ?
C12 C7 C8 C9 -11.5(4) . . . . ?

_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 1.872
_oxdiff_exptl_absorpt_empirical_full_min 0.499
####################################################################### 
# 
# 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_syl-06-20_01
_database_code_depnum_ccdc_archive 'CCDC 2281801'
loop_
_audit_author_name
_audit_author_address
'Tilo Soehnel'
;University of Auckland
New Zealand
;
_audit_update_record             
;
2023-07-16 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;
_audit_creation_date             2023-07-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H20 N4 O3'
_chemical_formula_sum            'C15 H20 N4 O3'
_chemical_formula_weight         304.35
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H20 N4 O3'
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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   16.2851(13)
_cell_length_b                   5.2346(4)
_cell_length_c                   18.9492(16)
_cell_angle_alpha                90
_cell_angle_beta                 112.304(10)
_cell_angle_gamma                90
_cell_volume                     1494.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1950
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      69.5320
_cell_measurement_theta_min      5.0640
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.794
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             648
_exptl_crystal_recrystallization_method MeOH
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4802
_diffrn_reflns_point_group_measured_fraction_full 0.793
_diffrn_reflns_point_group_measured_fraction_max 0.791
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.729
_diffrn_reflns_theta_min         5.874
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -36.00  14.40   0.80    2.60    --  -46.98  38.00   0.00   63
  2  ω     -8.00  18.40   0.80    2.60    --  -46.98  19.00   0.00   33
  3  ω    -26.00  35.60   0.80    2.60    --  -46.98  19.00  60.00   77
  4  ω    -32.00  29.60   0.80    2.60    --  -46.98  96.00  74.00   77
  5  ω    -45.00 -18.60   0.80   10.60    --  -90.25 111.00   0.00   33
  6  ω    -47.00 -12.60   0.80   10.60    --  -90.25  45.00  30.00   43
  7  ω    -47.00 -11.80   0.80   10.60    --  -90.25  45.00   0.00   44
  8  ω    -50.00 -22.00   0.80   10.60    --  -90.25  45.00 -90.00   35
  9  ω    -49.00 -17.00   0.80   10.60    --  -90.25  45.00-120.00   40
 10  ω    -43.00 -11.80   0.80   10.60    --  -90.25  45.00-150.00   39
 11  ω    -87.00 -24.60   0.80   10.60    --  -90.25  77.00  60.00   78
 12  ω    -79.00 -11.00   0.80   10.60    --  -90.25  96.00  74.00   85
 13  ω     23.00  57.40   0.80    2.60    --   46.98 -96.00 -34.00   43
 14  ω     62.00  86.80   0.80   10.60    --   97.33 -96.00 -34.00   31
 15  ω     61.00  85.80   0.80   10.60    --   97.33 -77.00   0.00   31
 16  ω     40.00  64.80   0.80   10.60    --   97.33 -61.00 -90.00   31
 17  ω     24.00  51.20   0.80   10.60    --   97.33 -77.00   0.00   34
 18  ω     20.00  45.60   0.80   10.60    --   97.33 -45.00 -90.00   32
 19  ω    -29.00  23.00   0.80    2.60    --   46.98 -19.00  30.00   65
 20  ω     26.00  67.60   0.80   10.60    --   97.33 -61.00 120.00   52
 21  ω     32.00  71.20   0.80   10.60    --   97.33 -61.00 150.00   49
 22  ω     20.00  47.20   0.80   10.60    --   97.33 -45.00 120.00   34
 23  ω    140.00 176.00   0.80   10.60    --   97.33 111.00  90.00   45
 24  ω    109.00 143.40   0.80   10.60    --   97.33 178.00 120.00   43
 25  ω     74.00  98.80   0.80   10.60    --   97.33 178.00 120.00   31
 26  ω   -128.00-103.20   0.80   10.60    --  -90.25 -96.00 -34.00   31
 27  ω   -152.00-106.40   0.80   10.60    --  -90.25 -61.00 -30.00   57
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0175935000
_diffrn_orient_matrix_UB_12      0.2575570000
_diffrn_orient_matrix_UB_13      0.0424800000
_diffrn_orient_matrix_UB_21      -0.0922417000
_diffrn_orient_matrix_UB_22      0.0953525000
_diffrn_orient_matrix_UB_23      -0.0532200000
_diffrn_orient_matrix_UB_31      -0.0404494000
_diffrn_orient_matrix_UB_32      -0.1054957000
_diffrn_orient_matrix_UB_33      0.0555774000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.434
_reflns_Friedel_fraction_full    0.544
_reflns_Friedel_fraction_max     0.543
_reflns_number_gt                1870
_reflns_number_total             2156
_reflns_odcompleteness_completeness 99.40
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Flack x determined using 496 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         2156
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0514
_refine_ls_restrained_S_all      1.043
_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)+(0.0874P)²+0.0661P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1298
_refine_ls_wR_factor_ref         0.1390
_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, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2A = N2-H2B
 0.86 with sigma of 0.02
 H2A-H2B
 1.56 with sigma of 0.02
3.a Riding coordinates:
 N4(H4)
3.b Ternary CH refined with riding coordinates:
 C10(H10)
3.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C12(H12A,H12B), C13(H13A,H13B)
3.d Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C2(H2), C3(H3A), C4(H4A), C5(H5), C8(H8)
3.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.20981(18) 1.1033(6) 0.39429(17) 0.0311(7) Uani 1 1 d . . . . .
O2 O 0.2636(2) 0.6030(7) 0.14472(18) 0.0415(8) Uani 1 1 d . . . . .
O3 O 0.1874(2) 0.2381(7) 0.12752(18) 0.0369(8) Uani 1 1 d . . . . .
N1 N -0.1058(2) 0.4782(8) 0.25236(19) 0.0287(8) Uani 1 1 d . . . . .
H1 H -0.141745 0.345770 0.241579 0.034 Uiso 1 1 calc R U . . .
N2 N 0.0945(2) 0.6746(8) 0.4759(2) 0.0297(8) Uani 1 1 d D . . . .
H2A H 0.137(2) 0.657(11) 0.5193(14) 0.036 Uiso 1 1 d D U . . .
H2B H 0.076(3) 0.602(10) 0.4339(16) 0.036 Uiso 1 1 d D U . . .
N3 N 0.2056(2) 0.6731(7) 0.39398(19) 0.0245(8) Uani 1 1 d . . . . .
H3 H 0.180470 0.533599 0.402224 0.029 Uiso 1 1 calc R U . . .
N4 N 0.2530(2) 0.6810(7) 0.28505(19) 0.0276(8) Uani 1 1 d . . . . .
H4 H 0.224846 0.821241 0.268152 0.033 Uiso 1 1 d R U . . .
C1 C -0.0648(2) 0.5737(9) 0.2067(2) 0.0275(10) Uani 1 1 d . . . . .
C2 C -0.0698(3) 0.4961(11) 0.1355(2) 0.0345(11) Uani 1 1 d . . . . .
H2 H -0.104032 0.351756 0.110924 0.041 Uiso 1 1 calc R U . . .
C3 C -0.0231(3) 0.6362(12) 0.1016(3) 0.0418(12) Uani 1 1 d . . . . .
H3A H -0.024442 0.585649 0.052996 0.050 Uiso 1 1 calc R U . . .
C4 C 0.0264(3) 0.8514(11) 0.1373(3) 0.0418(13) Uani 1 1 d . . . . .
H4A H 0.055786 0.948645 0.111581 0.050 Uiso 1 1 calc R U . . .
C5 C 0.0330(3) 0.9238(10) 0.2089(3) 0.0349(11) Uani 1 1 d . . . . .
H5 H 0.068628 1.066065 0.233408 0.042 Uiso 1 1 calc R U . . .
C6 C -0.0134(3) 0.7863(9) 0.2457(2) 0.0261(9) Uani 1 1 d . . . . .
C7 C -0.0245(2) 0.8121(8) 0.3165(2) 0.0239(9) Uani 1 1 d . . . . .
C8 C -0.0819(2) 0.6207(10) 0.3168(2) 0.0282(10) Uani 1 1 d . . . . .
H8 H -0.102225 0.591805 0.356945 0.034 Uiso 1 1 calc R U . . .
C9 C 0.0181(3) 1.0018(9) 0.3787(2) 0.0272(9) Uani 1 1 d . . . . .
H9A H -0.024030 1.042654 0.403386 0.033 Uiso 1 1 calc R U . . .
H9B H 0.029148 1.161215 0.355572 0.033 Uiso 1 1 calc R U . . .
C10 C 0.1062(3) 0.9126(9) 0.4405(2) 0.0264(9) Uani 1 1 d . . . . .
H10 H 0.124529 1.046256 0.481220 0.032 Uiso 1 1 calc R U . . .
C11 C 0.1785(2) 0.9008(9) 0.4073(2) 0.0244(9) Uani 1 1 d . . . . .
C12 C 0.2775(2) 0.6540(9) 0.3656(2) 0.0255(9) Uani 1 1 d . . . . .
H12A H 0.322172 0.786630 0.391286 0.031 Uiso 1 1 calc R U . . .
H12B H 0.306572 0.485847 0.380985 0.031 Uiso 1 1 calc R U . . .
C13 C 0.2077(3) 0.4622(9) 0.2393(2) 0.0291(10) Uani 1 1 d . . . . .
H13A H 0.143164 0.476092 0.227278 0.035 Uiso 1 1 calc R U . . .
H13B H 0.229279 0.303373 0.268901 0.035 Uiso 1 1 calc R U . . .
C14 C 0.2237(3) 0.4484(9) 0.1665(2) 0.0285(9) Uani 1 1 d . . . . .
C15 C 0.1975(3) 0.1981(11) 0.0569(3) 0.0427(13) Uani 1 1 d . . . . .
H15A H 0.165697 0.331905 0.020654 0.064 Uiso 1 1 calc R U . . .
H15B H 0.173207 0.030653 0.036200 0.064 Uiso 1 1 calc R U . . .
H15C H 0.260674 0.204095 0.065158 0.064 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 C11 1.242(5) . ?
O2 C14 1.205(5) . ?
O3 C14 1.333(6) . ?
O3 C15 1.426(5) . ?
N1 H1 0.8800 . ?
N1 C1 1.372(5) . ?
N1 C8 1.356(6) . ?
N2 H2A 0.85(2) . ?
N2 H2B 0.83(2) . ?
N2 C10 1.462(6) . ?
N3 H3 0.8800 . ?
N3 C11 1.328(6) . ?
N3 C12 1.465(4) . ?
N4 H4 0.8600 . ?
N4 C12 1.430(5) . ?
N4 C13 1.457(6) . ?
C1 C2 1.381(6) . ?
C1 C6 1.420(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.379(7) . ?
C3 H3A 0.9500 . ?
C3 C4 1.400(8) . ?
C4 H4A 0.9500 . ?
C4 C5 1.374(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.405(6) . ?
C6 C7 1.425(6) . ?
C7 C8 1.372(6) . ?
C7 C9 1.496(6) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.540(5) . ?
C10 H10 1.0000 . ?
C10 C11 1.531(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.499(6) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C14 O3 C15 117.2(4) . . ?
C1 N1 H1 125.5 . . ?
C8 N1 H1 125.5 . . ?
C8 N1 C1 109.0(4) . . ?
H2A N2 H2B 138(4) . . ?
C10 N2 H2A 110(4) . . ?
C10 N2 H2B 91(4) . . ?
C11 N3 H3 120.0 . . ?
C11 N3 C12 120.1(3) . . ?
C12 N3 H3 120.0 . . ?
C12 N4 H4 112.0 . . ?
C12 N4 C13 115.5(3) . . ?
C13 N4 H4 111.8 . . ?
N1 C1 C2 130.3(4) . . ?
N1 C1 C6 106.8(4) . . ?
C2 C1 C6 122.9(4) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 C1 117.5(5) . . ?
C3 C2 H2 121.3 . . ?
C2 C3 H3A 119.3 . . ?
C2 C3 C4 121.3(4) . . ?
C4 C3 H3A 119.3 . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 C3 120.9(4) . . ?
C5 C4 H4A 119.5 . . ?
C4 C5 H5 120.2 . . ?
C4 C5 C6 119.6(5) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C7 107.7(4) . . ?
C5 C6 C1 117.7(4) . . ?
C5 C6 C7 134.6(4) . . ?
C6 C7 C9 128.2(4) . . ?
C8 C7 C6 105.4(4) . . ?
C8 C7 C9 126.5(4) . . ?
N1 C8 C7 111.1(3) . . ?
N1 C8 H8 124.4 . . ?
C7 C8 H8 124.4 . . ?
C7 C9 H9A 108.6 . . ?
C7 C9 H9B 108.6 . . ?
C7 C9 C10 114.7(4) . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
N2 C10 C9 111.2(3) . . ?
N2 C10 H10 107.1 . . ?
N2 C10 C11 114.1(4) . . ?
C9 C10 H10 107.1 . . ?
C11 C10 C9 109.9(3) . . ?
C11 C10 H10 107.1 . . ?
O1 C11 N3 122.4(3) . . ?
O1 C11 C10 119.0(4) . . ?
N3 C11 C10 118.6(4) . . ?
N3 C12 H12A 108.2 . . ?
N3 C12 H12B 108.2 . . ?
N4 C12 N3 116.6(3) . . ?
N4 C12 H12A 108.2 . . ?
N4 C12 H12B 108.2 . . ?
H12A C12 H12B 107.3 . . ?
N4 C13 H13A 109.4 . . ?
N4 C13 H13B 109.4 . . ?
N4 C13 C14 111.1(4) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
O2 C14 O3 123.2(4) . . ?
O2 C14 C13 126.0(4) . . ?
O3 C14 C13 110.8(4) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
N1 C1 C2 C3 177.6(5) . . . . ?
N1 C1 C6 C5 -177.8(4) . . . . ?
N1 C1 C6 C7 0.6(5) . . . . ?
N2 C10 C11 O1 -161.4(4) . . . . ?
N2 C10 C11 N3 18.3(5) . . . . ?
N4 C13 C14 O2 -4.4(7) . . . . ?
N4 C13 C14 O3 175.6(3) . . . . ?
C1 N1 C8 C7 -0.5(5) . . . . ?
C1 C2 C3 C4 -1.0(7) . . . . ?
C1 C6 C7 C8 -0.8(5) . . . . ?
C1 C6 C7 C9 177.9(4) . . . . ?
C2 C1 C6 C5 1.0(6) . . . . ?
C2 C1 C6 C7 179.4(4) . . . . ?
C2 C3 C4 C5 2.8(8) . . . . ?
C3 C4 C5 C6 -2.6(8) . . . . ?
C4 C5 C6 C1 0.7(7) . . . . ?
C4 C5 C6 C7 -177.1(5) . . . . ?
C5 C6 C7 C8 177.2(5) . . . . ?
C5 C6 C7 C9 -4.1(8) . . . . ?
C6 C1 C2 C3 -0.9(7) . . . . ?
C6 C7 C8 N1 0.8(5) . . . . ?
C6 C7 C9 C10 -91.2(5) . . . . ?
C7 C9 C10 N2 -57.3(4) . . . . ?
C7 C9 C10 C11 69.9(5) . . . . ?
C8 N1 C1 C2 -178.8(5) . . . . ?
C8 N1 C1 C6 -0.1(5) . . . . ?
C8 C7 C9 C10 87.4(5) . . . . ?
C9 C7 C8 N1 -178.0(4) . . . . ?
C9 C10 C11 O1 73.0(5) . . . . ?
C9 C10 C11 N3 -107.3(4) . . . . ?
C11 N3 C12 N4 -83.5(5) . . . . ?
C12 N3 C11 O1 2.4(6) . . . . ?
C12 N3 C11 C10 -177.3(3) . . . . ?
C12 N4 C13 C14 -152.4(3) . . . . ?
C13 N4 C12 N3 -74.6(5) . . . . ?
C15 O3 C14 O2 0.3(7) . . . . ?
C15 O3 C14 C13 -179.7(4) . . . . ?

_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 2.755
_oxdiff_exptl_absorpt_empirical_full_min 0.645
