# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TM_JR_05_THF_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1983293'
loop_
_audit_author_name
_audit_author_address
'Jarl Ivar van der Vlugt'
;University of Amsterdam
Netherlands
;
_audit_update_record             
;
2020-02-11 deposited with the CCDC.	2020-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H14 N4 O'
_chemical_formula_weight         242.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.7490(3)
_cell_length_b                   7.7490(3)
_cell_length_c                   22.0320(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1322.96(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    123
_cell_measurement_theta_min      3.8133
_cell_measurement_theta_max      29.8118

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   0.7202
_exptl_transmission_factor_max   0.7458
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.304
_exptl_crystal_size_min          0.244
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker ApexII Triumph monochromator sealed tube'
_diffrn_measurement_method       'Photon 50 CMOS detector'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            63886
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.786
_diffrn_reflns_theta_max         28.700
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1719
_reflns_number_gt                1576
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.595
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 535 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1719
_refine_ls_number_parameters     84
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1171
_refine_ls_wR_factor_gt          0.1126
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_restrained_S_all      0.975
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.39965(17) 0.39965(17) 0.5000 0.0463(6) Uani 1 2 d S T P . .
N1 N 0.7468(2) 0.4358(2) 0.60698(6) 0.0308(4) Uani 1 1 d . . . . .
N2 N 0.3618(2) 0.8271(2) 0.56417(7) 0.0328(4) Uani 1 1 d . . . . .
C3 C 0.7037(2) 0.5434(2) 0.57523(7) 0.0196(3) Uani 1 1 d . . . . .
C2 C 0.78506(18) 0.78506(18) 0.5000 0.0152(4) Uani 1 2 d S T P . .
C1 C 0.64913(18) 0.68023(19) 0.53451(6) 0.0145(3) Uani 1 1 d . . . . .
C4 C 0.4878(2) 0.7613(2) 0.55138(6) 0.0195(3) Uani 1 1 d . . . . .
C5 C 0.7459(2) 0.97167(19) 0.48657(7) 0.0225(4) Uani 1 1 d . . . . .
H5A H 0.7839 1.0434 0.5207 0.034 Uiso 1 1 calc R U . . .
H5B H 0.6213 0.9860 0.4807 0.034 Uiso 1 1 calc R U . . .
H5C H 0.8069 1.0069 0.4496 0.034 Uiso 1 1 calc R U . . .
C7 C 0.2199(2) 0.1714(2) 0.46771(8) 0.0277(4) Uani 1 1 d . . . . .
H7A H 0.2921 0.0661 0.4667 0.033 Uiso 1 1 calc R U . . .
H7B H 0.1161 0.1533 0.4423 0.033 Uiso 1 1 calc R U . . .
C6 C 0.3206(3) 0.3283(3) 0.44716(8) 0.0405(5) Uani 1 1 d . . . . .
H6A H 0.4096 0.2948 0.4171 0.049 Uiso 1 1 calc R U . . .
H6B H 0.2425 0.4138 0.4282 0.049 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0568(10) 0.0568(10) 0.0254(9) -0.0072(8) 0.0072(8) -0.0410(12)
N1 0.0347(8) 0.0343(9) 0.0233(7) 0.0122(6) -0.0050(6) -0.0008(6)
N2 0.0230(7) 0.0463(10) 0.0291(8) 0.0010(7) 0.0030(6) 0.0062(7)
C3 0.0192(7) 0.0251(8) 0.0146(6) 0.0027(6) -0.0004(6) -0.0036(6)
C2 0.0158(6) 0.0158(6) 0.0140(8) -0.0001(5) 0.0001(5) -0.0046(7)
C1 0.0143(7) 0.0182(7) 0.0111(6) 0.0015(5) -0.0013(5) -0.0022(5)
C4 0.0194(7) 0.0247(8) 0.0144(6) 0.0027(5) -0.0007(5) -0.0021(6)
C5 0.0265(8) 0.0157(7) 0.0251(7) 0.0025(6) -0.0005(6) -0.0029(6)
C7 0.0253(8) 0.0249(8) 0.0329(9) -0.0037(7) 0.0011(7) -0.0059(7)
C6 0.0493(12) 0.0484(12) 0.0238(9) -0.0043(8) 0.0009(8) -0.0277(10)

_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 C6 1.427(2) . ?
O1 C6 1.427(2) 7_556 ?
N1 C3 1.138(2) . ?
N2 C4 1.137(2) . ?
C3 C1 1.452(2) . ?
C2 C5 1.5069(18) 7_556 ?
C2 C5 1.5069(18) . ?
C2 C1 1.532(2) 7_556 ?
C2 C1 1.532(2) . ?
C1 C4 1.448(2) . ?
C1 C1 1.558(3) 7_556 ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C7 C6 1.514(3) . ?
C7 C7 1.519(4) 7_556 ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 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
C6 O1 C6 109.5(2) . 7_556 ?
N1 C3 C1 179.7(2) . . ?
C5 C2 C5 115.18(18) 7_556 . ?
C5 C2 C1 117.88(9) 7_556 7_556 ?
C5 C2 C1 117.09(9) . 7_556 ?
C5 C2 C1 117.09(9) 7_556 . ?
C5 C2 C1 117.88(9) . . ?
C1 C2 C1 61.13(12) 7_556 . ?
C4 C1 C3 114.18(12) . . ?
C4 C1 C2 119.40(11) . . ?
C3 C1 C2 119.59(11) . . ?
C4 C1 C1 116.83(14) . 7_556 ?
C3 C1 C1 116.43(15) . 7_556 ?
C2 C1 C1 59.43(6) . 7_556 ?
N2 C4 C1 178.99(19) . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C6 C7 C7 102.08(11) . 7_556 ?
C6 C7 H7A 111.4 . . ?
C7 C7 H7A 111.4 7_556 . ?
C6 C7 H7B 111.4 . . ?
C7 C7 H7B 111.4 7_556 . ?
H7A C7 H7B 109.2 . . ?
O1 C6 C7 106.76(15) . . ?
O1 C6 H6A 110.4 . . ?
C7 C6 H6A 110.4 . . ?
O1 C6 H6B 110.4 . . ?
C7 C6 H6B 110.4 . . ?
H6A C6 H6B 108.6 . . ?

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.048

_shelx_res_file                  
;

    TM_JR_05_THF_0m_a.res created by SHELXL-2014/7


TITL TM_JR_05_THF_0m_a.res in P4(1)2(1)2
CELL  0.71073   7.7490   7.7490  22.0320   90.000   90.000   90.000
ZERR    4.000   0.0003   0.0003   0.0011    0.000    0.000    0.000
LATT -1
SYMM -X, -Y, 1/2+Z
SYMM 1/2-Y, 1/2+X, 1/4+Z
SYMM 1/2+Y, 1/2-X, 3/4+Z
SYMM 1/2-X, 1/2+Y, 1/4-Z
SYMM 1/2+X, 1/2-Y, 3/4-Z
SYMM Y, X, -Z
SYMM -Y, -X, 1/2-Z
SFAC C  H  N  O
UNIT 52  56  16  4
REM Old TITL TM_JR_05_THF_0m in P4(3)2(1)2
REM SHELXT solution in P4(1)2(1)2
REM R1 0.114,  Rweak 0.028,  Alpha 0.002,  Orientation as input
REM Flack x= -0.392 ( 0.394 ) from Parsons' quotients
REM Formula found by SHELXT:  C13 N4 O
L.S. 10
BOND $H
ACTA
FMAP 2
PLAN 10
SIZE 0.244 0.304 0.580
TEMP -123.160
WGHT    0.100000
FVAR       0.91217
O1    4    0.399652    0.399652    0.500000    10.50000    0.05679    0.05679 =
         0.02543   -0.00723    0.00723   -0.04099
N1    3    0.746829    0.435835    0.606980    11.00000    0.03474    0.03435 =
         0.02334    0.01221   -0.00500   -0.00081
N2    3    0.361782    0.827148    0.564173    11.00000    0.02298    0.04629 =
         0.02913    0.00095    0.00303    0.00618
C3    1    0.703661    0.543384    0.575235    11.00000    0.01920    0.02509 =
         0.01458    0.00272   -0.00042   -0.00364
C2    1    0.785062    0.785062    0.500000    10.50000    0.01584    0.01584 =
         0.01401   -0.00007    0.00007   -0.00462
C1    1    0.649131    0.680233    0.534507    11.00000    0.01427    0.01815 =
         0.01108    0.00154   -0.00135   -0.00224
C4    1    0.487837    0.761332    0.551383    11.00000    0.01936    0.02467 =
         0.01437    0.00273   -0.00073   -0.00214
C5    1    0.745857    0.971666    0.486570    11.00000    0.02655    0.01574 =
         0.02512    0.00250   -0.00046   -0.00286
AFIX 137
H5A   2    0.783885    1.043425    0.520668    11.00000   -1.50000
H5B   2    0.621327    0.986004    0.480676    11.00000   -1.50000
H5C   2    0.806862    1.006924    0.449633    11.00000   -1.50000
AFIX   0
C7    1    0.219872    0.171439    0.467712    11.00000    0.02525    0.02488 =
         0.03288   -0.00373    0.00112   -0.00594
AFIX  23
H7A   2    0.292075    0.066077    0.466723    11.00000   -1.20000
H7B   2    0.116076    0.153257    0.442306    11.00000   -1.20000
AFIX   0
C6    1    0.320621    0.328302    0.447161    11.00000    0.04935    0.04835 =
         0.02382   -0.00426    0.00091   -0.02773
AFIX  23
H6A   2    0.409559    0.294769    0.417136    11.00000   -1.20000
H6B   2    0.242493    0.413758    0.428171    11.00000   -1.20000
AFIX   0
HKLF 4

REM  TM_JR_05_THF_0m_a.res in P4(1)2(1)2
REM R1 =  0.0409 for    1576 Fo > 4sig(Fo)  and  0.0468 for all    1719 data
REM     84 parameters refined using      0 restraints

END

WGHT      0.0565      0.1373

REM Highest difference peak  0.168,  deepest hole -0.225,  1-sigma level  0.048
Q1    1   0.6371  0.6371  0.5000  10.50000  0.05    0.17
Q2    1   0.3629  0.3640  0.4129  11.00000  0.05    0.15
Q3    1   0.7251  0.7466  0.5243  11.00000  0.05    0.15
Q4    1   0.2583  0.2485  0.4530  11.00000  0.05    0.14
Q5    1   0.4251  0.7417  0.5735  11.00000  0.05    0.13
Q6    1   0.8532  1.1605  0.5966  11.00000  0.05    0.12
Q7    1   0.5633  0.5535  0.6514  11.00000  0.05    0.12
Q8    1   0.9187  0.5806  0.6335  11.00000  0.05    0.12
Q9    1   0.7237  0.5445  0.6049  11.00000  0.05    0.12
Q10   1   0.7089  0.4439  0.5698  11.00000  0.05    0.12
;
_shelx_res_checksum              71125
