# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1937215'
loop_
_audit_author_name
_audit_author_address
'Anthony Linden'
;University of Zurich
Switzerland
;
_audit_update_record             
;
2019-10-11 deposited with the CCDC.	2020-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        3-chlorotetrazine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C2 H Cl N4'
_chemical_formula_sum            'C2 H Cl N4'
_chemical_formula_weight         116.52

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   11.2724(5)
_cell_length_b                   6.2790(4)
_cell_length_c                   12.5272(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     886.67(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    160(1)
_cell_measurement_reflns_used    3146
_cell_measurement_theta_min      7.0950
_cell_measurement_theta_max      74.4240

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.02
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0151
0 0 -1 0.0091
-4 3 0 0.0648
4 -3 0 0.0648
5 3 -1 0.1311
-5 -3 1 0.0971
6 -2 -1 0.0908
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0005 0.0002 0.9996 0.1126 -0.0483 0.0111
0.0005 -0.0002 -0.9996 -0.1126 0.0483 -0.0111
-3.9959 2.9941 -0.0036 0.3236 0.8143 0.2661
3.9959 -2.9941 0.0036 -0.3236 -0.8143 -0.2661
4.9963 2.9997 -1.0012 0.1438 0.4420 -0.8971
-4.9963 -2.9997 1.0012 -0.1438 -0.4420 0.8971
5.9947 -1.9941 -0.9965 -0.3532 -0.6503 -0.6152
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.746
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    6.417
_shelx_estimated_absorpt_T_min   0.286
_shelx_estimated_absorpt_T_max   0.882
_exptl_absorpt_correction_T_min  0.382
_exptl_absorpt_correction_T_max  0.858
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
Analytical numeric absorption correction using a multifaceted crystal
model [Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897] 
plus an empirical absorption correction using spherical harmonics, 
implemented in the SCALE3 ABSPACK scaling algorithm.
CrysAlisPro, Version 1.171.39.13a (Rigaku Oxford Diffraction, 2016)
;
_oxdiff_exptl_absorpt_empirical_full_min 0.649
_oxdiff_exptl_absorpt_empirical_full_max 1.502
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;

_exptl_special_details           
;
Data collection and full structure determination
done by Dr. Olivier Blacque: olivier.blacque@chem.uzh.ch

Solvent used: ?
Cooling Device: Oxford Instruments Cryojet XL
Crystal mount: on a glass fibre
Frames collected: 1133
Seconds exposure per frame: 3.0-12.0
Degrees rotation per frame: 0.8
Crystal-detector distance (mm): 55.0
Client: Simon Schnell
Sample code: GD1801.cif_od
;

_diffrn_ambient_temperature      160(1)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Oxford Diffraction SuperNova, dual radiation diffractometer'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Atlas CCD area detector on \k goniostat'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            4312
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         7.070
_diffrn_reflns_theta_max         74.503
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             904
_reflns_number_gt                883
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
'CrysAlisPro, Version 1.171.39.13a (Rigaku Oxford Diffraction, 2017)'
_computing_cell_refinement       
'CrysAlisPro, Version 1.171.39.13a (Rigaku Oxford Diffraction, 2017)'
_computing_data_reduction        
'CrysAlisPro, Version 1.171.39.13a (Rigaku Oxford Diffraction, 2017)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018 (Sheldrick, 2015)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2018 and PLATON (Spek, 2015)'

_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)+(0.0494P)²+0.2063P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         903
_refine_ls_number_parameters     68
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0772
_refine_ls_wR_factor_gt          0.0768
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.060

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
C1 C 0.62566(9) 0.4815(2) 0.70490(11) 0.0252(3) Uani 1 1 d . . . . .
C2 C 0.61483(12) 0.5623(2) 0.90119(12) 0.0298(3) Uani 1 1 d . . . . .
H2 H 0.6118(14) 0.595(3) 0.9737(16) 0.036(5) Uiso 1 1 d . . . . .
Cl1 Cl 0.63237(3) 0.42953(6) 0.57112(3) 0.03602(17) Uani 1 1 d . . . . .
N1 N 0.53864(9) 0.38674(17) 0.75873(9) 0.0283(3) Uani 1 1 d . . . . .
N2 N 0.53351(10) 0.43057(17) 0.86238(9) 0.0300(3) Uani 1 1 d . . . . .
N3 N 0.70269(10) 0.65288(18) 0.84690(9) 0.0314(3) Uani 1 1 d . . . . .
N4 N 0.70861(9) 0.61032(17) 0.74323(10) 0.0297(3) Uani 1 1 d . . . . .

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
C1 0.0305(6) 0.0201(6) 0.0250(7) 0.0014(5) -0.0004(4) 0.0025(4)
C2 0.0378(7) 0.0273(7) 0.0243(7) -0.0012(5) 0.0016(5) 0.0002(5)
Cl1 0.0484(3) 0.0375(3) 0.0222(2) 0.00000(11) -0.00097(11) 0.00239(12)
N1 0.0325(6) 0.0235(5) 0.0288(6) -0.0003(4) 0.0020(4) -0.0026(4)
N2 0.0349(6) 0.0263(6) 0.0288(6) 0.0009(4) 0.0050(4) -0.0018(4)
N3 0.0374(6) 0.0274(6) 0.0293(6) -0.0024(4) -0.0008(4) -0.0044(4)
N4 0.0339(6) 0.0264(6) 0.0288(6) 0.0019(4) 0.0017(4) -0.0043(4)

_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
C1 N4 1.3265(16) . ?
C1 N1 1.3306(16) . ?
C1 Cl1 1.7090(14) . ?
C2 N2 1.3268(18) . ?
C2 N3 1.3294(18) . ?
C2 H2 0.93(2) . ?
N1 N2 1.3285(16) . ?
N3 N4 1.3276(16) . ?

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
N4 C1 N1 127.50(13) . . ?
N4 C1 Cl1 116.11(10) . . ?
N1 C1 Cl1 116.38(9) . . ?
N2 C2 N3 126.45(14) . . ?
N2 C2 H2 118.0(10) . . ?
N3 C2 H2 115.5(10) . . ?
N2 N1 C1 115.77(11) . . ?
C2 N2 N1 117.20(11) . . ?
N4 N3 C2 116.85(11) . . ?
C1 N4 N3 116.20(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N4 C1 N1 N2 1.47(18) . . . . ?
Cl1 C1 N1 N2 -179.17(9) . . . . ?
N3 C2 N2 N1 -1.1(2) . . . . ?
C1 N1 N2 C2 -0.16(16) . . . . ?
N2 C2 N3 N4 1.2(2) . . . . ?
N1 C1 N4 N3 -1.42(19) . . . . ?
Cl1 C1 N4 N3 179.22(9) . . . . ?
C2 N3 N4 C1 0.07(17) . . . . ?


_shelx_res_file                  
;
TITL exp_1631_a.res in Pbca
    x.res
    created by SHELXL-2018/3 at 17:46:24 on 05-Apr-2018
CELL 1.54184 11.272432 6.279025 12.527169 90 90 90
ZERR 8 0.000529 0.000413 0.000658 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H Cl N
UNIT 16 8 8 32

L.S. 10
PLAN  20
SIZE 0.02 0.13 0.26
BOND $H
CONF
fmap 2
acta
OMIT 0 2 0
REM <olex2.extras>
REM <HklSrc "%.\\exp_1631.hkl">
REM </olex2.extras>

WGHT    0.049400    0.206300
FVAR       6.85556
C1    1    0.625655    0.481454    0.704902    11.00000    0.03045    0.02006 =
         0.02499    0.00144   -0.00038    0.00249
C2    1    0.614828    0.562257    0.901187    11.00000    0.03775    0.02731 =
         0.02429   -0.00116    0.00156    0.00016
H2    2    0.611767    0.595236    0.973693    11.00000    0.03556
CL1   3    0.632367    0.429527    0.571122    11.00000    0.04837    0.03746 =
         0.02222    0.00000   -0.00097    0.00239
N1    4    0.538642    0.386736    0.758730    11.00000    0.03252    0.02346 =
         0.02878   -0.00032    0.00204   -0.00256
N2    4    0.533505    0.430566    0.862380    11.00000    0.03492    0.02629 =
         0.02882    0.00088    0.00501   -0.00180
N3    4    0.702694    0.652883    0.846902    11.00000    0.03745    0.02740 =
         0.02925   -0.00236   -0.00079   -0.00438
N4    4    0.708607    0.610320    0.743233    11.00000    0.03388    0.02639 =
         0.02879    0.00185    0.00166   -0.00432
HKLF 4




REM  exp_1631_a.res in Pbca
REM wR2 = 0.0772, GooF = S = 1.096, Restrained GooF = 1.096 for all data
REM R1 = 0.0281 for 883 Fo > 4sig(Fo) and 0.0285 for all 903 data
REM 68 parameters refined using 0 restraints

END

WGHT      0.0494      0.2059

REM Highest difference peak  0.161,  deepest hole -0.338,  1-sigma level  0.060
Q1    1   0.5286  0.5544  0.5711  11.00000  0.05    0.16
Q2    1   0.8767  0.5032  0.8789  11.00000  0.05    0.13
Q3    1   0.7514  0.4991  0.5769  11.00000  0.05    0.13
Q4    1   0.7378  0.6453  0.6837  11.00000  0.05    0.13
Q5    1   0.5430  0.2933  0.5709  11.00000  0.05    0.13
Q6    1   0.5245  0.4314  0.5234  11.00000  0.05    0.12
Q7    1   0.6188  0.4868  0.6625  11.00000  0.05    0.12
Q8    1   0.4860  0.3965  0.9135  11.00000  0.05    0.12
Q9    1   0.4392  0.5504  0.7809  11.00000  0.05    0.12
Q10   1   0.6056  0.6033  1.0733  11.00000  0.05    0.11
Q11   1   0.6506  0.5545  0.7214  11.00000  0.05    0.11
Q12   1   0.6268  0.9058  0.9183  11.00000  0.05    0.11
Q13   1   0.7166  0.4325  0.9015  11.00000  0.05    0.11
Q14   1   0.8795  0.5458  0.8299  11.00000  0.05    0.11
Q15   1   0.6232  0.5671  0.9973  11.00000  0.05    0.11
Q16   1   0.6572  0.4058  1.0496  11.00000  0.05    0.11
Q17   1   0.6246  0.3974  1.0499  11.00000  0.05    0.11
Q18   1   0.5922  0.4454  0.7316  11.00000  0.05    0.11
Q19   1   0.7397  0.3166  0.5719  11.00000  0.05    0.11
Q20   1   0.7486  0.5547  0.9310  11.00000  0.05    0.10
;
_shelx_res_checksum              55627

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

data_4
_database_code_depnum_ccdc_archive 'CCDC 1937217'
loop_
_audit_author_name
_audit_author_address
'Anthony Linden'
;University of Zurich
Switzerland
;
_audit_update_record             
;
2019-10-11 deposited with the CCDC.	2020-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        3-phenoxy-s-tetrazine
_chemical_name_common            ?
_chemical_melting_point          385
_chemical_formula_moiety         'C8 H6 N4 O'
_chemical_formula_sum            'C8 H6 N4 O'
_chemical_formula_weight         174.17

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

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

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

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

_cell_length_a                   10.7358(3)
_cell_length_b                   5.14454(12)
_cell_length_c                   14.9437(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.056(3)
_cell_angle_gamma                90
_cell_volume                     797.02(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    5042
_cell_measurement_theta_min      3.8220
_cell_measurement_theta_max      28.2460

_exptl_crystal_description       tablet
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.86585
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Empirical absorption correction using spherical harmonics,
implemented in the SCALE3 ABSPACK scaling algorithm.
CrysAlisPro, Version 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
;
_oxdiff_exptl_absorpt_empirical_full_min 0.902
_oxdiff_exptl_absorpt_empirical_full_max 1.241
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_exptl_special_details           
;
Data collection and full structure determination
done by Prof. Anthony Linden: anthony.linden@chem.uzh.ch

Solvent used: MeCN
Cooling Device: Oxford Instruments Cryojet XL
Crystal mount: on a glass fibre
Frames collected: 926
Seconds exposure per frame: 22.5
Degrees rotation per frame: 0.5
Crystal-detector distance (mm): 55.0
Client: Andrea Turrin
Sample code: AT-108-p  (GD1809)
;

_diffrn_ambient_temperature      160(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Oxford Diffraction SuperNova, dual radiation diffractometer'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Atlas CCD area detector on \k goniostat'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            9349
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.823
_diffrn_reflns_theta_max         29.233
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1936
_reflns_number_gt                1614
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
'CrysAlisPro, Version 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_cell_refinement       
'CrysAlisPro, Version 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_data_reduction        
'CrysAlisPro, Version 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_structure_solution    'SHELXT-2018 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018 (Sheldrick, 2015b)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2018 and PLATON (Spek, 2015)'

_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)+(0.0344P)²+0.2119P] 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     'SHELXL-2018 (Sheldrick, 2015b)'
_refine_ls_extinction_coef       0.012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1936
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0868
_refine_ls_wR_factor_gt          0.0801
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.034

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 0.65289(8) 0.11448(16) 0.72953(6) 0.0367(2) Uani 1 1 d . . . . .
N2 N 0.55646(8) 0.18954(19) 0.84196(6) 0.0314(2) Uani 1 1 d . . . . .
N3 N 0.54273(9) 0.3360(2) 0.91087(6) 0.0347(2) Uani 1 1 d . . . . .
N5 N 0.71081(9) 0.6146(2) 0.89275(6) 0.0343(2) Uani 1 1 d . . . . .
N6 N 0.72693(9) 0.46655(19) 0.82355(6) 0.0302(2) Uani 1 1 d . . . . .
C1 C 0.64699(10) 0.2667(2) 0.80030(7) 0.0270(2) Uani 1 1 d . . . . .
C4 C 0.61842(12) 0.5456(3) 0.93188(8) 0.0374(3) Uani 1 1 d . . . . .
H4 H 0.604556 0.655585 0.979454 0.045 Uiso 1 1 calc R U . . .
C5 C 0.74851(10) 0.1625(2) 0.68158(7) 0.0284(2) Uani 1 1 d . . . . .
C6 C 0.84939(11) -0.0091(2) 0.69616(8) 0.0352(3) Uani 1 1 d . . . . .
H6 H 0.857060 -0.146619 0.739685 0.042 Uiso 1 1 calc R U . . .
C7 C 0.94000(11) 0.0232(2) 0.64570(9) 0.0399(3) Uani 1 1 d . . . . .
H7 H 1.010974 -0.093006 0.654752 0.048 Uiso 1 1 calc R U . . .
C8 C 0.92767(11) 0.2228(2) 0.58252(8) 0.0371(3) Uani 1 1 d . . . . .
H8 H 0.990240 0.244189 0.548336 0.045 Uiso 1 1 calc R U . . .
C9 C 0.82433(12) 0.3922(2) 0.56877(8) 0.0377(3) Uani 1 1 d . . . . .
H9 H 0.815885 0.529173 0.524982 0.045 Uiso 1 1 calc R U . . .
C10 C 0.73292(11) 0.3623(2) 0.61884(8) 0.0348(3) Uani 1 1 d . . . . .
H10 H 0.661471 0.477229 0.609886 0.042 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 0.0392(5) 0.0357(5) 0.0405(5) -0.0114(4) 0.0198(4) -0.0127(4)
N2 0.0264(5) 0.0339(5) 0.0354(5) 0.0044(4) 0.0110(4) -0.0007(4)
N3 0.0305(5) 0.0428(6) 0.0337(5) 0.0043(4) 0.0136(4) 0.0018(4)
N5 0.0375(5) 0.0368(5) 0.0315(5) -0.0059(4) 0.0142(4) -0.0044(4)
N6 0.0299(5) 0.0324(5) 0.0307(5) -0.0042(4) 0.0119(4) -0.0040(4)
C1 0.0244(5) 0.0286(5) 0.0287(5) 0.0009(4) 0.0079(4) 0.0002(4)
C4 0.0398(6) 0.0430(7) 0.0337(6) -0.0042(5) 0.0174(5) -0.0011(5)
C5 0.0290(5) 0.0286(5) 0.0293(5) -0.0078(4) 0.0104(4) -0.0058(4)
C6 0.0355(6) 0.0311(6) 0.0370(6) 0.0008(5) 0.0056(5) 0.0003(5)
C7 0.0305(6) 0.0369(7) 0.0522(7) -0.0055(6) 0.0108(5) 0.0048(5)
C8 0.0350(6) 0.0398(7) 0.0413(6) -0.0114(5) 0.0185(5) -0.0063(5)
C9 0.0453(7) 0.0351(6) 0.0354(6) 0.0019(5) 0.0153(5) -0.0008(5)
C10 0.0333(6) 0.0329(6) 0.0396(6) -0.0001(5) 0.0120(5) 0.0055(5)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3306(13) . ?
O1 C5 1.4180(13) . ?
N2 N3 1.3148(13) . ?
N2 C1 1.3431(13) . ?
N3 C4 1.3375(16) . ?
N5 C4 1.3240(15) . ?
N5 N6 1.3312(12) . ?
N6 C1 1.3266(14) . ?
C4 H4 0.9500 . ?
C5 C6 1.3701(16) . ?
C5 C10 1.3719(16) . ?
C6 C7 1.3869(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.3781(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.3833(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.3884(16) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C5 119.30(8) . . ?
N3 N2 C1 115.82(9) . . ?
N2 N3 C4 117.46(9) . . ?
C4 N5 N6 116.96(10) . . ?
C1 N6 N5 116.16(9) . . ?
N6 C1 O1 120.20(9) . . ?
N6 C1 N2 127.19(10) . . ?
O1 C1 N2 112.60(9) . . ?
N5 C4 N3 126.25(11) . . ?
N5 C4 H4 116.9 . . ?
N3 C4 H4 116.9 . . ?
C6 C5 C10 122.86(10) . . ?
C6 C5 O1 116.96(10) . . ?
C10 C5 O1 120.01(10) . . ?
C5 C6 C7 118.26(11) . . ?
C5 C6 H6 120.9 . . ?
C7 C6 H6 120.9 . . ?
C8 C7 C6 120.37(11) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 120.11(11) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C10 120.15(11) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C5 C10 C9 118.25(11) . . ?
C5 C10 H10 120.9 . . ?
C9 C10 H10 120.9 . . ?

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
C1 N2 N3 C4 0.55(14) . . . . ?
C4 N5 N6 C1 0.88(15) . . . . ?
N5 N6 C1 O1 177.36(9) . . . . ?
N5 N6 C1 N2 -3.82(16) . . . . ?
C5 O1 C1 N6 2.33(15) . . . . ?
C5 O1 C1 N2 -176.65(9) . . . . ?
N3 N2 C1 N6 3.07(16) . . . . ?
N3 N2 C1 O1 -178.04(9) . . . . ?
N6 N5 C4 N3 2.64(18) . . . . ?
N2 N3 C4 N5 -3.40(18) . . . . ?
C1 O1 C5 C6 107.19(12) . . . . ?
C1 O1 C5 C10 -77.38(13) . . . . ?
C10 C5 C6 C7 0.63(17) . . . . ?
O1 C5 C6 C7 175.92(10) . . . . ?
C5 C6 C7 C8 -0.22(18) . . . . ?
C6 C7 C8 C9 -0.21(18) . . . . ?
C7 C8 C9 C10 0.26(18) . . . . ?
C6 C5 C10 C9 -0.59(17) . . . . ?
O1 C5 C10 C9 -175.73(10) . . . . ?
C8 C9 C10 C5 0.13(18) . . . . ?


_shelx_res_file                  
;
TITL gd1809_mo_a.res in P2(1)/c
    x.res
    created by SHELXL-2018/3 at 11:16:16 on 16-Oct-2018
REM Old TITL GD1809_Mo in P2(1)/c
REM SHELXT solution in P2(1)/c: R1 0.154, Rweak 0.150, Alpha 0.012
REM <I/s> 0.413 for 190 systematic absences, Orientation as input
REM Formula found by SHELXT: C9 O1
CELL 0.71073 10.7358 5.14454 14.9437 90 105.056 90
ZERR 4 0.0003 0.00012 0.0004 0 0.003 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 32 24 16 4

L.S. 4
PLAN  10
TEMP -113
BOND $H
CONF
fmap 2
acta

WGHT    0.034400    0.211900
EXTI    0.011828
FVAR       5.59380
O1    4    0.652892    0.114475    0.729530    11.00000    0.03918    0.03570 =
         0.04050   -0.01138    0.01980   -0.01266
N2    3    0.556459    0.189539    0.841965    11.00000    0.02636    0.03394 =
         0.03543    0.00438    0.01097   -0.00073
N3    3    0.542732    0.336023    0.910871    11.00000    0.03051    0.04279 =
         0.03366    0.00429    0.01361    0.00182
N5    3    0.710813    0.614551    0.892749    11.00000    0.03755    0.03682 =
         0.03155   -0.00587    0.01420   -0.00445
N6    3    0.726933    0.466548    0.823547    11.00000    0.02987    0.03238 =
         0.03067   -0.00415    0.01185   -0.00398
C1    1    0.646990    0.266658    0.800304    11.00000    0.02440    0.02860 =
         0.02872    0.00092    0.00793    0.00022
C4    1    0.618421    0.545621    0.931884    11.00000    0.03978    0.04298 =
         0.03369   -0.00416    0.01742   -0.00106
AFIX  43
H4    2    0.604556    0.655585    0.979454    11.00000   -1.20000
AFIX   0
C5    1    0.748512    0.162508    0.681575    11.00000    0.02899    0.02858 =
         0.02926   -0.00779    0.01042   -0.00577
C6    1    0.849387   -0.009113    0.696156    11.00000    0.03551    0.03107 =
         0.03699    0.00082    0.00559    0.00026
AFIX  43
H6    2    0.857060   -0.146619    0.739685    11.00000   -1.20000
AFIX   0
C7    1    0.940002    0.023166    0.645703    11.00000    0.03049    0.03693 =
         0.05223   -0.00550    0.01082    0.00479
AFIX  43
H7    2    1.010974   -0.093006    0.654752    11.00000   -1.20000
AFIX   0
C8    1    0.927667    0.222816    0.582515    11.00000    0.03502    0.03980 =
         0.04130   -0.01137    0.01849   -0.00633
AFIX  43
H8    2    0.990240    0.244189    0.548336    11.00000   -1.20000
AFIX   0
C9    1    0.824329    0.392157    0.568773    11.00000    0.04533    0.03507 =
         0.03545    0.00185    0.01528   -0.00077
AFIX  43
H9    2    0.815885    0.529173    0.524982    11.00000   -1.20000
AFIX   0
C10   1    0.732923    0.362317    0.618838    11.00000    0.03334    0.03285 =
         0.03964   -0.00008    0.01196    0.00549
AFIX  43
H10   2    0.661471    0.477229    0.609886    11.00000   -1.20000
AFIX   0
HKLF 4




REM  gd1809_mo_a.res in P2(1)/c
REM wR2 = 0.0868, GooF = S = 1.048, Restrained GooF = 1.048 for all data
REM R1 = 0.0345 for 1614 Fo > 4sig(Fo) and 0.0445 for all 1936 data
REM 119 parameters refined using 0 restraints

END

WGHT      0.0344      0.2120

REM Highest difference peak  0.197,  deepest hole -0.186,  1-sigma level  0.034
Q1    1   0.7637  0.3151  0.6754  11.00000  0.05    0.20
Q2    1   0.7792  0.0257  0.6737  11.00000  0.05    0.19
Q3    1   0.8185  0.1440  0.7087  11.00000  0.05    0.18
Q4    1   0.7610  0.3156  0.5797  11.00000  0.05    0.16
Q5    1   0.5064  0.2760  0.9528  11.00000  0.05    0.15
Q6    1   0.9123  0.0393  0.6851  11.00000  0.05    0.15
Q7    1   0.9571  0.1713  0.6353  11.00000  0.05    0.15
Q8    1   0.7317  0.2231  0.6399  11.00000  0.05    0.14
Q9    1   0.7203  0.3093  0.8361  11.00000  0.05    0.14
Q10   1   0.8947  0.3340  0.5994  11.00000  0.05    0.14
;
_shelx_res_checksum              90414

#   End of CIF   ============================================================
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 1937218'
loop_
_audit_author_name
_audit_author_address
'Anthony Linden'
;University of Zurich
Switzerland
;
_audit_update_record             
;
2019-10-11 deposited with the CCDC.	2020-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        1-(S-tetrazin-3-yl)-1H-indole
_chemical_name_common            ?
_chemical_melting_point          377
_chemical_formula_moiety         'C10 H7 N5'
_chemical_formula_sum            'C10 H7 N5'
_chemical_formula_weight         197.21

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'

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

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

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

_cell_length_a                   38.7645(3)
_cell_length_b                   11.93147(14)
_cell_length_c                   7.70847(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3565.30(6)
_cell_formula_units_Z            16
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    6471
_cell_measurement_theta_min      4.5210
_cell_measurement_theta_max      73.9210

_exptl_crystal_description       tablet
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_F_000             1632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.794
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.90730
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Empirical absorption correction using spherical harmonics,
implemented in the SCALE3 ABSPACK scaling algorithm.
CrysAlisPro, Version 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
;
_oxdiff_exptl_absorpt_empirical_full_min 0.845
_oxdiff_exptl_absorpt_empirical_full_max 1.165
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_exptl_special_details           
;
Data collection and full structure determination
done by Prof. Anthony Linden: anthony.linden@chem.uzh.ch

Solvent used: diethyl ether
Cooling Device: Oxford Instruments Cryojet XL
Crystal mount: on a glass fibre
Frames collected: 1757
Seconds exposure per frame: 3.5-14.0
Degrees rotation per frame: 1.0
Crystal-detector distance (mm): 55.0
Client: Simon Schnell
Sample code: SDS-1012-P  (GD1901)
;

_diffrn_ambient_temperature      160(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Oxford Diffraction SuperNova, dual radiation diffractometer'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Atlas CCD area detector on \k goniostat'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            8381
_diffrn_reflns_av_unetI/netI     0.0076
_diffrn_reflns_av_R_equivalents  0.0132
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.563
_diffrn_reflns_theta_max         74.042
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             1702
_reflns_number_gt                1689
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.777
_reflns_Friedel_fraction_max     0.893
_reflns_Friedel_fraction_full    0.925

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

_computing_data_collection       
'CrysAlisPro, Version 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_cell_refinement       
'CrysAlisPro, Version 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_data_reduction        
'CrysAlisPro, Version 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_structure_solution    'SHELXT-2018 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018 (Sheldrick, 2015b)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2018 and PLATON (Spek, 2015)'

_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)+(0.0379P)²+1.6158P] 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     'SHELXL-2018 (Sheldrick, 2015b)'
_refine_ls_extinction_coef       0.00026(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 740 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1702
_refine_ls_number_parameters     137
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0230
_refine_ls_R_factor_gt           0.0228
_refine_ls_wR_factor_ref         0.0608
_refine_ls_wR_factor_gt          0.0607
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.113
_refine_diff_density_rms         0.028

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
N1 N 0.29234(3) 0.50734(12) 0.55233(18) 0.0319(3) Uani 1 1 d . . . . .
N2 N 0.26286(3) 0.47495(13) 0.4840(2) 0.0370(3) Uani 1 1 d . . . . .
N3 N 0.29225(3) 0.34842(13) 0.2985(2) 0.0364(4) Uani 1 1 d . . . . .
N4 N 0.32219(3) 0.38125(12) 0.36368(17) 0.0307(3) Uani 1 1 d . . . . .
N5 N 0.35200(3) 0.50510(10) 0.54220(15) 0.0238(3) Uani 1 1 d . . . . .
C1 C 0.32118(4) 0.46358(13) 0.48191(19) 0.0248(3) Uani 1 1 d . . . . .
C2 C 0.26405(4) 0.40007(16) 0.3554(2) 0.0383(4) Uani 1 1 d . . . . .
H2 H 0.242893 0.382156 0.299654 0.046 Uiso 1 1 calc R U . . .
C3 C 0.35470(4) 0.59120(13) 0.6662(2) 0.0286(3) Uani 1 1 d . . . . .
H3 H 0.335785 0.629695 0.717096 0.034 Uiso 1 1 calc R U . . .
C4 C 0.38808(4) 0.61065(13) 0.7016(2) 0.0299(3) Uani 1 1 d . . . . .
H4 H 0.396687 0.664387 0.781590 0.036 Uiso 1 1 calc R U . . .
C5 C 0.40850(4) 0.53616(12) 0.5976(2) 0.0254(3) Uani 1 1 d . . . . .
C6 C 0.44408(4) 0.51916(13) 0.5824(2) 0.0302(3) Uani 1 1 d . . . . .
H6 H 0.459818 0.562268 0.649287 0.036 Uiso 1 1 calc R U . . .
C7 C 0.45590(4) 0.43858(14) 0.4685(2) 0.0301(3) Uani 1 1 d . . . . .
H7 H 0.479995 0.425948 0.457446 0.036 Uiso 1 1 calc R U . . .
C8 C 0.43284(4) 0.37532(14) 0.3691(2) 0.0284(3) Uani 1 1 d . . . . .
H8 H 0.441639 0.320876 0.290810 0.034 Uiso 1 1 calc R U . . .
C9 C 0.39735(4) 0.39012(13) 0.3820(2) 0.0260(3) Uani 1 1 d . . . . .
H9 H 0.381761 0.346870 0.314411 0.031 Uiso 1 1 calc R U . . .
C10 C 0.38565(4) 0.47087(12) 0.49784(17) 0.0220(3) Uani 1 1 d . . . . .

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
N1 0.0256(6) 0.0347(7) 0.0354(7) 0.0023(6) 0.0064(5) 0.0018(5)
N2 0.0236(6) 0.0436(8) 0.0437(8) 0.0061(7) 0.0047(6) 0.0015(5)
N3 0.0276(7) 0.0461(9) 0.0356(7) -0.0020(7) -0.0023(6) -0.0062(6)
N4 0.0232(6) 0.0365(8) 0.0323(7) -0.0036(6) 0.0004(6) -0.0031(5)
N5 0.0244(6) 0.0235(6) 0.0233(6) -0.0002(5) 0.0027(5) 0.0012(4)
C1 0.0244(7) 0.0263(8) 0.0237(7) 0.0062(6) 0.0032(5) 0.0001(5)
C2 0.0239(7) 0.0500(11) 0.0409(9) 0.0051(8) -0.0021(7) -0.0037(7)
C3 0.0362(8) 0.0243(8) 0.0253(7) -0.0023(6) 0.0045(6) 0.0031(6)
C4 0.0372(8) 0.0244(8) 0.0280(8) -0.0030(6) -0.0005(7) -0.0019(6)
C5 0.0304(7) 0.0221(7) 0.0237(6) 0.0027(5) -0.0011(6) -0.0031(6)
C6 0.0286(7) 0.0307(8) 0.0313(8) 0.0008(6) -0.0047(6) -0.0069(6)
C7 0.0219(6) 0.0326(8) 0.0356(8) 0.0024(7) 0.0001(6) -0.0009(6)
C8 0.0262(7) 0.0287(8) 0.0303(8) -0.0012(6) 0.0027(6) 0.0015(6)
C9 0.0256(7) 0.0255(8) 0.0270(7) -0.0026(5) -0.0004(6) -0.0019(5)
C10 0.0225(6) 0.0214(7) 0.0220(7) 0.0035(5) 0.0000(5) -0.0006(5)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.3164(19) . ?
N1 C1 1.3479(18) . ?
N2 C2 1.336(2) . ?
N3 N4 1.3241(18) . ?
N3 C2 1.329(2) . ?
N4 C1 1.341(2) . ?
N5 C1 1.3744(18) . ?
N5 C3 1.4070(19) . ?
N5 C10 1.4087(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.343(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.435(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.399(2) . ?
C5 C10 1.408(2) . ?
C6 C7 1.380(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.399(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(2) . ?
C9 H9 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
N2 N1 C1 116.44(14) . . ?
N1 N2 C2 117.61(14) . . ?
N4 N3 C2 117.28(15) . . ?
N3 N4 C1 116.71(13) . . ?
C1 N5 C3 123.88(12) . . ?
C1 N5 C10 128.18(12) . . ?
C3 N5 C10 107.93(12) . . ?
N4 C1 N1 125.58(14) . . ?
N4 C1 N5 117.95(13) . . ?
N1 C1 N5 116.43(14) . . ?
N3 C2 N2 125.69(15) . . ?
N3 C2 H2 117.2 . . ?
N2 C2 H2 117.2 . . ?
C4 C3 N5 109.63(13) . . ?
C4 C3 H3 125.2 . . ?
N5 C3 H3 125.2 . . ?
C3 C4 C5 108.11(13) . . ?
C3 C4 H4 125.9 . . ?
C5 C4 H4 125.9 . . ?
C6 C5 C10 119.62(14) . . ?
C6 C5 C4 132.87(14) . . ?
C10 C5 C4 107.51(12) . . ?
C7 C6 C5 118.78(14) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C6 C7 C8 120.82(14) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 121.65(15) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C10 C9 C8 117.18(14) . . ?
C10 C9 H9 121.4 . . ?
C8 C9 H9 121.4 . . ?
C9 C10 C5 121.95(13) . . ?
C9 C10 N5 131.23(13) . . ?
C5 C10 N5 106.82(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C2 1.7(2) . . . . ?
C2 N3 N4 C1 0.2(2) . . . . ?
N3 N4 C1 N1 7.2(2) . . . . ?
N3 N4 C1 N5 -175.23(14) . . . . ?
N2 N1 C1 N4 -8.2(2) . . . . ?
N2 N1 C1 N5 174.17(12) . . . . ?
C3 N5 C1 N4 -179.92(14) . . . . ?
C10 N5 C1 N4 -1.2(2) . . . . ?
C3 N5 C1 N1 -2.1(2) . . . . ?
C10 N5 C1 N1 176.61(13) . . . . ?
N4 N3 C2 N2 -6.6(3) . . . . ?
N1 N2 C2 N3 5.5(3) . . . . ?
C1 N5 C3 C4 178.25(13) . . . . ?
C10 N5 C3 C4 -0.70(16) . . . . ?
N5 C3 C4 C5 0.44(18) . . . . ?
C3 C4 C5 C6 -179.39(16) . . . . ?
C3 C4 C5 C10 -0.01(18) . . . . ?
C10 C5 C6 C7 0.3(2) . . . . ?
C4 C5 C6 C7 179.64(17) . . . . ?
C5 C6 C7 C8 0.3(2) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
C7 C8 C9 C10 0.1(2) . . . . ?
C8 C9 C10 C5 0.5(2) . . . . ?
C8 C9 C10 N5 -179.26(15) . . . . ?
C6 C5 C10 C9 -0.8(2) . . . . ?
C4 C5 C10 C9 179.74(13) . . . . ?
C6 C5 C10 N5 179.06(13) . . . . ?
C4 C5 C10 N5 -0.41(16) . . . . ?
C1 N5 C10 C9 1.6(2) . . . . ?
C3 N5 C10 C9 -179.50(15) . . . . ?
C1 N5 C10 C5 -178.22(13) . . . . ?
C3 N5 C10 C5 0.67(15) . . . . ?


_shelx_res_file                  
;
TITL gd1901_cu_a.res in Fdd2
    x.res
    created by SHELXL-2018/3 at 08:55:43 on 22-Jan-2019
REM Old TITL GD1901_Cu in Fdd2
REM SHELXT solution in Fdd2: R1 0.080, Rweak 0.018, Alpha 0.002
REM <I/s> 1.169 for 63 systematic absences, Orientation as input
REM Flack x = -0.029 ( 0.105 ) from 740 Parsons' quotients
REM Formula found by SHELXT: N4 N2
CELL 1.54184 38.7645 11.93147 7.70847 90 90 90
ZERR 16 0.0003 0.00014 0.00008 0 0 0
LATT -4
SYMM -X,-Y,+Z
SYMM 0.25+X,0.25-Y,0.25+Z
SYMM 0.25-X,0.25+Y,0.25+Z
SFAC C H N
UNIT 160 112 80
TEMP -113
L.S. 4
PLAN  10
BOND $H
CONF
fmap 2
ACTA
WGHT    0.037900    1.615800
EXTI    0.000259
FVAR       2.23389
N1    3    0.292344    0.507340    0.552327    11.00000    0.02559    0.03469 =
         0.03537    0.00233    0.00643    0.00182
N2    3    0.262859    0.474946    0.484027    11.00000    0.02357    0.04364 =
         0.04370    0.00613    0.00465    0.00148
N3    3    0.292246    0.348416    0.298459    11.00000    0.02756    0.04612 =
         0.03561   -0.00203   -0.00229   -0.00624
N4    3    0.322187    0.381252    0.363680    11.00000    0.02317    0.03646 =
         0.03233   -0.00362    0.00038   -0.00313
N5    3    0.352002    0.505103    0.542200    11.00000    0.02437    0.02354 =
         0.02334   -0.00019    0.00275    0.00117
C1    1    0.321180    0.463580    0.481908    11.00000    0.02436    0.02625 =
         0.02370    0.00624    0.00321    0.00010
C2    1    0.264046    0.400066    0.355363    11.00000    0.02394    0.04996 =
         0.04092    0.00510   -0.00213   -0.00373
AFIX  43
H2    2    0.242893    0.382156    0.299654    11.00000   -1.20000
AFIX   0
C3    1    0.354699    0.591198    0.666192    11.00000    0.03625    0.02435 =
         0.02534   -0.00228    0.00453    0.00306
AFIX  43
H3    2    0.335785    0.629695    0.717096    11.00000   -1.20000
AFIX   0
C4    1    0.388082    0.610653    0.701602    11.00000    0.03721    0.02437 =
         0.02805   -0.00303   -0.00050   -0.00189
AFIX  43
H4    2    0.396687    0.664387    0.781590    11.00000   -1.20000
AFIX   0
C5    1    0.408495    0.536163    0.597613    11.00000    0.03036    0.02214 =
         0.02370    0.00272   -0.00113   -0.00307
C6    1    0.444079    0.519156    0.582418    11.00000    0.02859    0.03067 =
         0.03126    0.00081   -0.00474   -0.00690
AFIX  43
H6    2    0.459818    0.562268    0.649287    11.00000   -1.20000
AFIX   0
C7    1    0.455898    0.438583    0.468478    11.00000    0.02194    0.03261 =
         0.03563    0.00240    0.00015   -0.00094
AFIX  43
H7    2    0.479995    0.425948    0.457446    11.00000   -1.20000
AFIX   0
C8    1    0.432838    0.375323    0.369085    11.00000    0.02625    0.02871 =
         0.03035   -0.00117    0.00271    0.00151
AFIX  43
H8    2    0.441639    0.320876    0.290810    11.00000   -1.20000
AFIX   0
C9    1    0.397348    0.390120    0.381956    11.00000    0.02563    0.02548 =
         0.02701   -0.00258   -0.00040   -0.00185
AFIX  43
H9    2    0.381761    0.346870    0.314411    11.00000   -1.20000
AFIX   0
C10   1    0.385645    0.470874    0.497839    11.00000    0.02253    0.02140 =
         0.02197    0.00354    0.00004   -0.00063
HKLF 4




REM  gd1901_cu_a.res in Fdd2
REM wR2 = 0.0608, GooF = S = 1.072, Restrained GooF = 1.072 for all data
REM R1 = 0.0228 for 1689 Fo > 4sig(Fo) and 0.0230 for all 1702 data
REM 137 parameters refined using 1 restraints

END

WGHT      0.0379      1.6157

REM Highest difference peak  0.154,  deepest hole -0.113,  1-sigma level  0.028
Q1    1   0.3998  0.5161  0.5236  11.00000  0.05    0.15
Q2    1   0.3681  0.4815  0.5093  11.00000  0.05    0.13
Q3    1   0.3391  0.4844  0.5277  11.00000  0.05    0.13
Q4    1   0.3893  0.4509  0.4054  11.00000  0.05    0.13
Q5    1   0.4247  0.5432  0.5857  11.00000  0.05    0.12
Q6    1   0.3282  0.6223  0.6628  11.00000  0.05    0.12
Q7    1   0.4164  0.4011  0.3551  11.00000  0.05    0.11
Q8    1   0.4008  0.5896  0.6338  11.00000  0.05    0.11
Q9    1   0.3897  0.4087  0.4709  11.00000  0.05    0.10
Q10   1   0.5000  0.5000  0.5863  10.50000  0.05    0.10
;
_shelx_res_checksum              5611

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

data_39
_database_code_depnum_ccdc_archive 'CCDC 1958903'
loop_
_audit_author_name
_audit_author_address
'Anthony Linden'
;University of Zurich
Switzerland
;
_audit_update_record             
;
2019-10-11 deposited with the CCDC.	2020-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
N-(2-((3-nitropyridin-2-yl)disulfaneyl)ethyl)-1,2,4,5-tetrazin-3-amine
_chemical_name_common            ?
_chemical_melting_point          419
_chemical_formula_moiety         'C9 H9 N7 O2 S2'
_chemical_formula_sum            'C9 H9 N7 O2 S2'
_chemical_formula_weight         311.35

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   17.7417(3)
_cell_length_b                   6.22991(9)
_cell_length_c                   23.2377(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.9389(13)
_cell_angle_gamma                90
_cell_volume                     2562.38(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    10728
_cell_measurement_theta_min      3.4450
_cell_measurement_theta_max      30.1500

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.429
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.92715
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Empirical absorption correction using spherical harmonics,
implemented in the SCALE3 ABSPACK scaling algorithm.
CrysAlisPro, Version 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
;
_oxdiff_exptl_absorpt_empirical_full_min 0.857
_oxdiff_exptl_absorpt_empirical_full_max 1.161
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_exptl_special_details           
;
Data collection and full structure determination
done by Prof. Anthony Linden: anthony.linden@chem.uzh.ch

Solvent used: dichloromethane / MeCN
Cooling Device: Oxford Instruments Cryojet XL
Crystal mount: on a glass fibre
Frames collected: 479
Seconds exposure per frame: 22.5
Degrees rotation per frame: 1.0
Crystal-detector distance (mm): 55.0
Client: Simon Schnell
Sample code: SDS-1335  (GD1907)
;

_diffrn_ambient_temperature      160(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Oxford Diffraction SuperNova, dual radiation diffractometer'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Atlas CCD area detector on \k goniostat'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            16497
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.798
_diffrn_reflns_theta_max         30.243
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3564
_reflns_number_gt                3204
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
'CrysAlisPro, Version 1.171.40.53 (Rigaku Oxford Diffraction, 2019)'
_computing_cell_refinement       
'CrysAlisPro, Version 1.171.40.53 (Rigaku Oxford Diffraction, 2019)'
_computing_data_reduction        
'CrysAlisPro, Version 1.171.40.53 (Rigaku Oxford Diffraction, 2019)'
_computing_structure_solution    'SHELXT-2018 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018 (Sheldrick, 2015b)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2018 and PLATON (Spek, 2015)'

_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)+(0.0311P)²+1.7110P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   'geom & difmap'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018 (Sheldrick, 2015b)'
_refine_ls_extinction_coef       0.00065(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3564
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0266
_refine_ls_wR_factor_ref         0.0704
_refine_ls_wR_factor_gt          0.0674
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.043

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.64207(2) 0.54574(5) 0.38324(2) 0.02476(8) Uani 1 1 d . . . . .
S2 S 0.73012(2) 0.75303(4) 0.37744(2) 0.02511(8) Uani 1 1 d . . . . .
O1 O 0.83856(5) 1.04284(15) 0.38084(4) 0.0379(2) Uani 1 1 d . . . . .
O2 O 0.93928(6) 1.0761(2) 0.43758(5) 0.0536(3) Uani 1 1 d . . . . .
N1 N 0.54222(6) 0.22570(18) 0.17947(4) 0.0335(2) Uani 1 1 d . . . . .
N2 N 0.50849(6) 0.0577(2) 0.15526(5) 0.0373(3) Uani 1 1 d . . . . .
N3 N 0.58369(6) -0.17751(17) 0.21508(5) 0.0317(2) Uani 1 1 d . . . . .
N4 N 0.61854(6) -0.01249(16) 0.24072(4) 0.0267(2) Uani 1 1 d . . . . .
N5 N 0.63217(7) 0.35502(17) 0.24674(4) 0.0302(2) Uani 1 1 d . . . . .
H5 H 0.6158(9) 0.479(3) 0.2363(7) 0.040(4) Uiso 1 1 d . . . . .
N6 N 0.78195(5) 0.48480(16) 0.46100(4) 0.0260(2) Uani 1 1 d . . . . .
N7 N 0.88208(6) 0.97890(18) 0.42069(5) 0.0316(2) Uani 1 1 d . . . . .
C1 C 0.59722(6) 0.18554(19) 0.22214(4) 0.0234(2) Uani 1 1 d . . . . .
C2 C 0.53015(8) -0.1371(2) 0.17376(6) 0.0385(3) Uani 1 1 d . . . . .
H2 H 0.505120 -0.256917 0.155843 0.046 Uiso 1 1 calc R U . . .
C3 C 0.69657(7) 0.3320(2) 0.28849(5) 0.0317(3) Uani 1 1 d . . . . .
H31 H 0.729068 0.460549 0.286390 0.038 Uiso 1 1 calc R U . . .
H32 H 0.726594 0.206125 0.277699 0.038 Uiso 1 1 calc R U . . .
C4 C 0.67566(6) 0.30440(18) 0.34987(5) 0.0250(2) Uani 1 1 d . . . . .
H41 H 0.720483 0.251086 0.373316 0.030 Uiso 1 1 calc R U . . .
H42 H 0.635917 0.193078 0.350620 0.030 Uiso 1 1 calc R U . . .
C5 C 0.79705(6) 0.66655(18) 0.43366(4) 0.0223(2) Uani 1 1 d . . . . .
C6 C 0.83145(7) 0.4130(2) 0.50287(5) 0.0306(3) Uani 1 1 d . . . . .
H6 H 0.819904 0.283567 0.522020 0.037 Uiso 1 1 calc R U . . .
C7 C 0.89845(7) 0.5167(2) 0.51978(5) 0.0332(3) Uani 1 1 d . . . . .
H7 H 0.931986 0.459853 0.549586 0.040 Uiso 1 1 calc R U . . .
C8 C 0.91489(7) 0.7038(2) 0.49221(5) 0.0309(3) Uani 1 1 d . . . . .
H8 H 0.960053 0.780488 0.502681 0.037 Uiso 1 1 calc R U . . .
C9 C 0.86423(6) 0.77879(19) 0.44872(5) 0.0253(2) Uani 1 1 d . . . . .

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
S1 0.01912(13) 0.02601(15) 0.02840(14) -0.00407(10) -0.00378(10) -0.00020(10)
S2 0.02540(14) 0.01837(14) 0.03034(15) -0.00132(10) -0.00691(10) -0.00136(10)
O1 0.0354(5) 0.0309(5) 0.0468(5) 0.0029(4) -0.0024(4) -0.0064(4)
O2 0.0511(6) 0.0611(7) 0.0471(6) -0.0015(5) -0.0084(5) -0.0367(6)
N1 0.0354(6) 0.0377(6) 0.0265(5) -0.0003(4) -0.0050(4) 0.0066(5)
N2 0.0279(5) 0.0539(7) 0.0292(5) -0.0102(5) -0.0058(4) 0.0027(5)
N3 0.0361(5) 0.0258(5) 0.0331(5) -0.0071(4) 0.0013(4) -0.0048(4)
N4 0.0294(5) 0.0236(5) 0.0265(5) -0.0032(4) -0.0030(4) -0.0014(4)
N5 0.0445(6) 0.0217(5) 0.0240(5) -0.0005(4) -0.0016(4) -0.0040(4)
N6 0.0249(5) 0.0289(5) 0.0234(4) -0.0013(4) -0.0047(4) -0.0028(4)
N7 0.0302(5) 0.0329(5) 0.0318(5) -0.0095(4) 0.0023(4) -0.0108(4)
C1 0.0259(5) 0.0257(5) 0.0185(5) -0.0020(4) 0.0019(4) 0.0004(4)
C2 0.0336(6) 0.0416(7) 0.0391(7) -0.0158(6) -0.0051(5) -0.0074(6)
C3 0.0277(6) 0.0337(6) 0.0337(6) -0.0119(5) 0.0031(5) -0.0092(5)
C4 0.0254(5) 0.0186(5) 0.0295(5) -0.0019(4) -0.0077(4) -0.0011(4)
C5 0.0208(5) 0.0240(5) 0.0217(5) -0.0070(4) -0.0011(4) -0.0005(4)
C6 0.0305(6) 0.0373(6) 0.0231(5) 0.0012(5) -0.0043(4) -0.0010(5)
C7 0.0266(6) 0.0475(7) 0.0244(5) -0.0035(5) -0.0062(4) 0.0015(5)
C8 0.0216(5) 0.0439(7) 0.0267(5) -0.0111(5) -0.0026(4) -0.0055(5)
C9 0.0231(5) 0.0289(6) 0.0239(5) -0.0093(4) 0.0017(4) -0.0036(4)

_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
S1 C4 1.8112(12) . ?
S1 S2 2.0384(4) . ?
S2 C5 1.7873(11) . ?
O1 N7 1.2303(14) . ?
O2 N7 1.2232(14) . ?
N1 N2 1.3130(16) . ?
N1 C1 1.3656(14) . ?
N2 C2 1.3350(19) . ?
N3 N4 1.3205(14) . ?
N3 C2 1.3275(17) . ?
N4 C1 1.3525(15) . ?
N5 C1 1.3332(15) . ?
N5 C3 1.4543(16) . ?
N5 H5 0.856(17) . ?
N6 C5 1.3344(15) . ?
N6 C6 1.3420(15) . ?
N7 C9 1.4515(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.5080(17) . ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
C4 H41 0.9900 . ?
C4 H42 0.9900 . ?
C5 C9 1.4052(15) . ?
C6 C7 1.3860(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.3712(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.3866(17) . ?
C8 H8 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
C4 S1 S2 102.79(4) . . ?
C5 S2 S1 103.55(4) . . ?
N2 N1 C1 116.54(11) . . ?
N1 N2 C2 118.30(10) . . ?
N4 N3 C2 117.92(11) . . ?
N3 N4 C1 117.01(10) . . ?
C1 N5 C3 121.93(11) . . ?
C1 N5 H5 117.2(11) . . ?
C3 N5 H5 120.9(11) . . ?
C5 N6 C6 119.03(10) . . ?
O2 N7 O1 123.03(12) . . ?
O2 N7 C9 118.88(11) . . ?
O1 N7 C9 118.09(10) . . ?
N5 C1 N4 118.29(10) . . ?
N5 C1 N1 117.02(11) . . ?
N4 C1 N1 124.69(10) . . ?
N3 C2 N2 125.53(12) . . ?
N3 C2 H2 117.2 . . ?
N2 C2 H2 117.2 . . ?
N5 C3 C4 114.16(10) . . ?
N5 C3 H31 108.7 . . ?
C4 C3 H31 108.7 . . ?
N5 C3 H32 108.7 . . ?
C4 C3 H32 108.7 . . ?
H31 C3 H32 107.6 . . ?
C3 C4 S1 114.82(8) . . ?
C3 C4 H41 108.6 . . ?
S1 C4 H41 108.6 . . ?
C3 C4 H42 108.6 . . ?
S1 C4 H42 108.6 . . ?
H41 C4 H42 107.5 . . ?
N6 C5 C9 119.90(10) . . ?
N6 C5 S2 117.30(8) . . ?
C9 C5 S2 122.79(9) . . ?
N6 C6 C7 123.78(12) . . ?
N6 C6 H6 118.1 . . ?
C7 C6 H6 118.1 . . ?
C8 C7 C6 118.02(11) . . ?
C8 C7 H7 121.0 . . ?
C6 C7 H7 121.0 . . ?
C7 C8 C9 118.61(11) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C8 C9 C5 120.67(11) . . ?
C8 C9 N7 117.77(10) . . ?
C5 C9 N7 121.54(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C2 -0.09(17) . . . . ?
C2 N3 N4 C1 -0.75(16) . . . . ?
C3 N5 C1 N4 5.97(17) . . . . ?
C3 N5 C1 N1 -173.78(10) . . . . ?
N3 N4 C1 N5 -179.13(11) . . . . ?
N3 N4 C1 N1 0.61(17) . . . . ?
N2 N1 C1 N5 179.57(11) . . . . ?
N2 N1 C1 N4 -0.17(17) . . . . ?
N4 N3 C2 N2 0.6(2) . . . . ?
N1 N2 C2 N3 -0.1(2) . . . . ?
C1 N5 C3 C4 -87.15(14) . . . . ?
N5 C3 C4 S1 -73.55(12) . . . . ?
S2 S1 C4 C3 -58.14(8) . . . . ?
C6 N6 C5 C9 0.36(16) . . . . ?
C6 N6 C5 S2 178.99(9) . . . . ?
S1 S2 C5 N6 7.52(9) . . . . ?
S1 S2 C5 C9 -173.90(8) . . . . ?
C5 N6 C6 C7 -0.15(18) . . . . ?
N6 C6 C7 C8 0.2(2) . . . . ?
C6 C7 C8 C9 -0.47(18) . . . . ?
C7 C8 C9 C5 0.69(17) . . . . ?
C7 C8 C9 N7 179.04(11) . . . . ?
N6 C5 C9 C8 -0.64(17) . . . . ?
S2 C5 C9 C8 -179.19(9) . . . . ?
N6 C5 C9 N7 -178.93(10) . . . . ?
S2 C5 C9 N7 2.53(15) . . . . ?
O2 N7 C9 C8 -2.30(17) . . . . ?
O1 N7 C9 C8 177.75(11) . . . . ?
O2 N7 C9 C5 176.03(12) . . . . ?
O1 N7 C9 C5 -3.91(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N5 H5 N3 0.856(17) 2.258(17) 3.1106(16) 173.5(15) 1_565 yes


_shelx_res_file                  
;
TITL gd1907_mo_a.res in C2/c
    x.res
    created by SHELXL-2018/3 at 17:14:49 on 11-Sep-2019
REM Old TITL GD1907_Mo in C2/c
REM SHELXT solution in C2/c: R1 0.135, Rweak 0.096, Alpha 0.019
REM <I/s> 0.838 for 250 systematic absences, Orientation as input
REM Formula found by SHELXT: C2 N7 O1 S2
CELL 0.71073 17.7417 6.22991 23.2377 90 93.9389 90
ZERR 8 0.0003 0.00009 0.0003 0 0.0013 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H N O S
UNIT 72 72 56 16 16

L.S. 4
PLAN  10
TEMP -113
BOND $H
CONF
EQIV $1 x, y+1, z
HTAB N5 N3_$1
fmap 2
acta
WGHT    0.031100    1.711000
EXTI    0.000654
FVAR       2.67902
S1    5    0.642072    0.545737    0.383241    11.00000    0.01912    0.02601 =
         0.02840   -0.00407   -0.00378   -0.00020
S2    5    0.730119    0.753034    0.377435    11.00000    0.02540    0.01837 =
         0.03034   -0.00132   -0.00691   -0.00136
O1    4    0.838562    1.042840    0.380842    11.00000    0.03543    0.03086 =
         0.04683    0.00287   -0.00238   -0.00640
O2    4    0.939276    1.076129    0.437585    11.00000    0.05108    0.06108 =
         0.04709   -0.00145   -0.00843   -0.03670
N1    3    0.542219    0.225705    0.179473    11.00000    0.03541    0.03767 =
         0.02647   -0.00034   -0.00498    0.00660
N2    3    0.508493    0.057690    0.155264    11.00000    0.02788    0.05391 =
         0.02916   -0.01025   -0.00584    0.00272
N3    3    0.583689   -0.177507    0.215080    11.00000    0.03610    0.02582 =
         0.03310   -0.00713    0.00128   -0.00478
N4    3    0.618544   -0.012490    0.240720    11.00000    0.02936    0.02357 =
         0.02654   -0.00318   -0.00304   -0.00137
N5    3    0.632169    0.355024    0.246741    11.00000    0.04448    0.02168 =
         0.02395   -0.00053   -0.00158   -0.00398
H5    2    0.615776    0.479369    0.236340    11.00000    0.03976
N6    3    0.781947    0.484802    0.460995    11.00000    0.02490    0.02886 =
         0.02344   -0.00131   -0.00471   -0.00284
N7    3    0.882076    0.978897    0.420686    11.00000    0.03016    0.03286 =
         0.03177   -0.00951    0.00229   -0.01081
C1    1    0.597223    0.185542    0.222139    11.00000    0.02587    0.02574 =
         0.01853   -0.00201    0.00195    0.00043
C2    1    0.530147   -0.137084    0.173764    11.00000    0.03363    0.04163 =
         0.03912   -0.01581   -0.00507   -0.00743
AFIX  43
H2    2    0.505120   -0.256917    0.155843    11.00000   -1.20000
AFIX   0
C3    1    0.696565    0.332005    0.288492    11.00000    0.02773    0.03374 =
         0.03374   -0.01186    0.00313   -0.00921
AFIX  23
H31   2    0.729068    0.460549    0.286390    11.00000   -1.20000
H32   2    0.726594    0.206125    0.277699    11.00000   -1.20000
AFIX   0
C4    1    0.675658    0.304399    0.349869    11.00000    0.02540    0.01864 =
         0.02952   -0.00190   -0.00775   -0.00114
AFIX  23
H41   2    0.720483    0.251086    0.373316    11.00000   -1.20000
H42   2    0.635917    0.193078    0.350620    11.00000   -1.20000
AFIX   0
C5    1    0.797055    0.666548    0.433662    11.00000    0.02078    0.02400 =
         0.02169   -0.00701   -0.00108   -0.00052
C6    1    0.831451    0.412972    0.502868    11.00000    0.03051    0.03733 =
         0.02308    0.00116   -0.00431   -0.00102
AFIX  43
H6    2    0.819904    0.283567    0.522020    11.00000   -1.20000
AFIX   0
C7    1    0.898452    0.516697    0.519780    11.00000    0.02661    0.04752 =
         0.02443   -0.00348   -0.00618    0.00147
AFIX  43
H7    2    0.931986    0.459853    0.549586    11.00000   -1.20000
AFIX   0
C8    1    0.914895    0.703819    0.492206    11.00000    0.02163    0.04394 =
         0.02667   -0.01107   -0.00264   -0.00546
AFIX  43
H8    2    0.960053    0.780488    0.502681    11.00000   -1.20000
AFIX   0
C9    1    0.864233    0.778792    0.448715    11.00000    0.02314    0.02886 =
         0.02386   -0.00930    0.00169   -0.00364
HKLF 4




REM  gd1907_mo_a.res in C2/c
REM wR2 = 0.0704, GooF = S = 1.060, Restrained GooF = 1.060 for all data
REM R1 = 0.0266 for 3204 Fo > 4sig(Fo) and 0.0309 for all 3564 data
REM 186 parameters refined using 0 restraints

END

WGHT      0.0311      1.7110

REM Highest difference peak  0.318,  deepest hole -0.215,  1-sigma level  0.043
Q1    1   0.6820  0.3049  0.3196  11.00000  0.05    0.32
Q2    1   0.8313  0.7300  0.4378  11.00000  0.05    0.29
Q3    1   0.9616  0.9825  0.4311  11.00000  0.05    0.28
Q4    1   0.5515 -0.1353  0.2006  11.00000  0.05    0.25
Q5    1   0.7700  0.6973  0.4064  11.00000  0.05    0.24
Q6    1   0.8704  0.4562  0.5039  11.00000  0.05    0.24
Q7    1   0.8984  0.7137  0.4618  11.00000  0.05    0.24
Q8    1   0.5731  0.1991  0.2026  11.00000  0.05    0.24
Q9    1   0.8066  0.4604  0.4806  11.00000  0.05    0.22
Q10   1   0.8816  0.7704  0.4765  11.00000  0.05    0.22
;
_shelx_res_checksum              67775

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1937216'
loop_
_audit_author_name
_audit_author_address
'Anthony Linden'
;University of Zurich
Switzerland
;
_audit_update_record             
;
2019-10-11 deposited with the CCDC.	2020-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        3-bromotetrazine
_chemical_name_common            ?
_chemical_melting_point          344
_chemical_formula_moiety         'C2 H Br N4'
_chemical_formula_sum            'C2 H Br N4'
_chemical_formula_weight         160.98

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'
Br Br -0.6763 1.2805 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   12.7468(5)
_cell_length_b                   5.60166(19)
_cell_length_c                   12.9507(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     924.72(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    2980
_cell_measurement_theta_min      3.3990
_cell_measurement_theta_max      73.5270

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0230
0 0 -1 0.0230
-1 0 0 0.0387
1 0 0 0.0410
1 4 -1 0.1284
5 -3 1 0.0956
-5 -1 0 0.0549
-5 1 0 0.0735
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0001 0.0008 1.0016 -0.0028 0.1188 -0.0088
-0.0001 -0.0008 -1.0016 0.0028 -0.1188 0.0088
-0.9993 -0.0012 -0.0011 0.0312 0.0092 0.1164
0.9993 0.0012 0.0011 -0.0312 -0.0092 -0.1164
0.9696 3.9958 -1.0084 -1.0890 -0.1317 0.1767
5.0190 -2.9899 1.0131 0.6364 0.0753 -0.8040
-4.9892 -1.0047 -0.0036 0.4214 0.0472 0.5108
-5.0041 0.9930 -0.0076 -0.1089 0.0453 0.6530
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.313
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    10.963
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.481
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model 
plus an empirical absorption correction using spherical harmonics, 
implemented in the SCALE3 ABSPACK scaling algorithm.
CrysAlisPro, Version 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
;
_oxdiff_exptl_absorpt_empirical_full_min 0.742
_oxdiff_exptl_absorpt_empirical_full_max 1.469
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_exptl_special_details           
;
Data collection and full structure determination
done by Prof. Anthony Linden: anthony.linden@chem.uzh.ch

Solvent used: ?
Cooling Device: Oxford Instruments Cryojet XL
Crystal mount: on a glass fibre
Frames collected: 1001
Seconds exposure per frame: 1.0-4.0
Degrees rotation per frame: 1.0
Crystal-detector distance (mm): 55.0
Client: Simon Schnell
Sample code: SJS-505-p  (GD1803)
;

_diffrn_ambient_temperature      160(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Oxford Diffraction SuperNova, dual radiation diffractometer'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Atlas CCD area detector on \k goniostat'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            4719
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         6.838
_diffrn_reflns_theta_max         73.945
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             926
_reflns_number_gt                904
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
'CrysAlisPro, Version 1.171.38.46 (Rigaku Oxford Diffraction, 2017)'
_computing_cell_refinement       
'CrysAlisPro, Version 1.171.38.46 (Rigaku Oxford Diffraction, 2017)'
_computing_data_reduction        
'CrysAlisPro, Version 1.171.38.46 (Rigaku Oxford Diffraction, 2017)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018 (Sheldrick, 2015b)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2018 and PLATON (Spek, 2015)'

_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)+(0.0285P)²+0.4717P] 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     'SHELXL-2018 (Sheldrick, 2015b)'
_refine_ls_extinction_coef       0.00063(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         926
_refine_ls_number_parameters     65
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0189
_refine_ls_R_factor_gt           0.0185
_refine_ls_wR_factor_ref         0.0516
_refine_ls_wR_factor_gt          0.0512
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.067

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
Br1 Br 0.64681(2) 0.32371(4) 0.47504(2) 0.02773(12) Uani 1 1 d . . . . .
N2 N 0.58488(13) 0.6809(3) 0.34389(14) 0.0258(4) Uani 1 1 d . . . . .
N3 N 0.57115(14) 0.7764(3) 0.25079(15) 0.0291(3) Uani 1 1 d . . . . .
N5 N 0.66335(13) 0.4512(3) 0.17470(12) 0.0265(3) Uani 1 1 d . . . . .
N6 N 0.67731(13) 0.3547(3) 0.26716(12) 0.0230(3) Uani 1 1 d . . . . .
C1 C 0.63477(13) 0.4721(3) 0.34604(14) 0.0203(3) Uani 1 1 d . . . . .
C4 C 0.60915(17) 0.6547(3) 0.17069(16) 0.0297(4) Uani 1 1 d . . . . .
H4 H 0.596353 0.719338 0.104045 0.036 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
Br1 0.03190(18) 0.03146(17) 0.01984(15) 0.00168(6) 0.00010(7) -0.00041(7)
N2 0.0220(8) 0.0242(8) 0.0311(9) -0.0034(6) 0.0017(7) 0.0007(5)
N3 0.0230(8) 0.0265(8) 0.0378(8) 0.0052(7) -0.0014(7) 0.0008(6)
N5 0.0264(8) 0.0316(8) 0.0216(7) -0.0004(6) 0.0015(6) -0.0020(6)
N6 0.0223(8) 0.0244(7) 0.0223(7) -0.0015(6) -0.0002(6) 0.0009(6)
C1 0.0190(8) 0.0213(8) 0.0207(8) 0.0001(7) -0.0010(6) -0.0014(6)
C4 0.0262(11) 0.0337(10) 0.0292(10) 0.0076(8) -0.0020(8) -0.0020(7)

_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
Br1 C1 1.8723(19) . ?
N2 N3 1.331(2) . ?
N2 C1 1.332(2) . ?
N3 C4 1.333(3) . ?
N5 N6 1.326(2) . ?
N5 C4 1.334(3) . ?
N6 C1 1.330(2) . ?
C4 H4 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
N3 N2 C1 115.79(16) . . ?
N2 N3 C4 116.86(16) . . ?
N6 N5 C4 116.93(16) . . ?
N5 N6 C1 115.94(15) . . ?
N6 C1 N2 127.78(17) . . ?
N6 C1 Br1 115.61(13) . . ?
N2 C1 Br1 116.61(14) . . ?
N3 C4 N5 126.53(19) . . ?
N3 C4 H4 116.7 . . ?
N5 C4 H4 116.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N2 N3 C4 -0.5(2) . . . . ?
C4 N5 N6 C1 0.4(2) . . . . ?
N5 N6 C1 N2 -4.0(3) . . . . ?
N5 N6 C1 Br1 175.90(12) . . . . ?
N3 N2 C1 N6 4.0(3) . . . . ?
N3 N2 C1 Br1 -175.86(13) . . . . ?
N2 N3 C4 N5 -2.9(3) . . . . ?
N6 N5 C4 N3 3.0(3) . . . . ?


_shelx_res_file                  
;
TITL gd1803_a.res in Pbca
    x.res
    created by SHELXL-2018/1 at 17:51:47 on 06-Mar-2018
REM Old TITL GD1803 in Pbca
REM SHELXT solution in Pbca
REM R1 0.073, Rweak 0.003, Alpha 0.019, Orientation as input
REM Formula found by SHELXT: C6 Br
CELL 1.54184 12.7468 5.60166 12.9507 90 90 90
ZERR 8 0.0005 0.00019 0.0004 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H Br N
UNIT 16 8 8 32
TEMP -113
L.S. 10
PLAN  10
BOND $H
CONF
fmap 2
ACTA
WGHT    0.028500    0.471700
EXTI    0.000631
FVAR       3.50941
BR1   3    0.646811    0.323707    0.475037    11.00000    0.03190    0.03146 =
         0.01984    0.00168    0.00010   -0.00041
N2    4    0.584883    0.680903    0.343886    11.00000    0.02205    0.02423 =
         0.03113   -0.00337    0.00169    0.00074
N3    4    0.571151    0.776433    0.250792    11.00000    0.02304    0.02650 =
         0.03775    0.00521   -0.00135    0.00076
N5    4    0.663354    0.451197    0.174696    11.00000    0.02637    0.03157 =
         0.02160   -0.00037    0.00154   -0.00196
N6    4    0.677312    0.354742    0.267156    11.00000    0.02231    0.02437 =
         0.02231   -0.00154   -0.00021    0.00087
C1    1    0.634772    0.472126    0.346045    11.00000    0.01898    0.02126 =
         0.02071    0.00008   -0.00100   -0.00137
C4    1    0.609148    0.654714    0.170686    11.00000    0.02616    0.03367 =
         0.02916    0.00757   -0.00204   -0.00196
AFIX  43
H4    2    0.596353    0.719338    0.104045    11.00000   -1.20000
AFIX   0
HKLF 4




REM  gd1803_a.res in Pbca
REM R1 =  0.0185 for     904 Fo > 4sig(Fo)  and  0.0189 for all     926 data
REM     65 parameters refined using      0 restraints

END

WGHT      0.0285      0.4717

REM Highest difference peak  0.324,  deepest hole -0.434,  1-sigma level  0.067
Q1    1   0.6458  0.1610  0.4383  11.00000  0.05    0.32
Q2    1   0.6600  0.3185  0.2474  11.00000  0.05    0.27
Q3    1   0.6075  0.5819  0.3335  11.00000  0.05    0.27
Q4    1   0.6557  0.4988  0.5201  11.00000  0.05    0.25
Q5    1   0.6424  0.4695  0.4484  11.00000  0.05    0.22
Q6    1   0.6543  0.4269  0.3058  11.00000  0.05    0.22
Q7    1   0.6404  0.3402  0.3875  11.00000  0.05    0.22
Q8    1   0.6518  0.1831  0.3300  11.00000  0.05    0.21
Q9    1   0.6424  0.1541  0.5114  11.00000  0.05    0.20
Q10   1   0.6409  0.5647  0.1814  11.00000  0.05    0.20
;
_shelx_res_checksum              50521

#   End of CIF   ============================================================

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_23
_database_code_depnum_ccdc_archive 'CCDC 1937219'
loop_
_audit_author_name
_audit_author_address
'Anthony Linden'
;University of Zurich
Switzerland
;
_audit_update_record             
;
2019-10-11 deposited with the CCDC.	2020-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        Boc-Tyr(Tet)-OMe
_chemical_name_common            ?
_chemical_melting_point          393
_chemical_formula_moiety         'C17 H21 N5 O5'
_chemical_formula_sum            'C17 H21 N5 O5'
_chemical_formula_weight         375.39

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

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

_cell_length_a                   32.663(2)
_cell_length_b                   5.1610(2)
_cell_length_c                   11.0162(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.704(5)
_cell_angle_gamma                90
_cell_volume                     1850.79(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    3168
_cell_measurement_theta_min      4.0210
_cell_measurement_theta_max      71.0480

_exptl_crystal_description       needle
_exptl_crystal_colour            pink
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.849
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.56496
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Empirical absorption correction using spherical harmonics,
implemented in the SCALE3 ABSPACK scaling algorithm.
CrysAlisPro, Version 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
;
_oxdiff_exptl_absorpt_empirical_full_min 0.663
_oxdiff_exptl_absorpt_empirical_full_max 1.650
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_exptl_special_details           
;
Data collection and full structure determination
done by Prof. Anthony Linden: anthony.linden@chem.uzh.ch

Solvent used: diethyl ether
Cooling Device: Oxford Instruments Cryojet XL
Crystal mount: on a glass fibre
Frames collected: 2601
Seconds exposure per frame: 6.0-30.0
Degrees rotation per frame: 1.0
Crystal-detector distance (mm): 55.0
Client: Simon Schnell
Sample code: SDS-1062-p  (GD1902)
;

_diffrn_ambient_temperature      160(2)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle κ-geometry diffractometer'
_diffrn_measurement_device_type  
'Oxford Diffraction SuperNova, dual radiation diffractometer'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Atlas CCD area detector on \k goniostat'
_diffrn_detector_area_resol_mean 10.3801
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            13382
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.715
_diffrn_reflns_theta_max         73.150
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             3606
_reflns_number_gt                2965
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_max     0.942
_reflns_Friedel_fraction_full    0.971

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

_computing_data_collection       
'CrysAlisPro, Version 1.171.40.39a (Rigaku Oxford Diffraction, 2019)'
_computing_cell_refinement       
'CrysAlisPro, Version 1.171.40.39a (Rigaku Oxford Diffraction, 2019)'
_computing_data_reduction        
'CrysAlisPro, Version 1.171.40.39a (Rigaku Oxford Diffraction, 2019)'
_computing_structure_solution    'SHELXT-2018 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018 (Sheldrick, 2015b)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2018 and PLATON (Spek, 2015)'

_refine_special_details          
;
The available crystals were very thin, malleable, weakly diffracting 
needles which probably suffered from layer slippage, as the diffraction 
pattern in one direction was quite messy, suggesting that the crystal was 
composed of many slightly rotated domains.  Thus the final results are not 
of optimum quality, although the overall structure is unambiguous.

The amide H atom was placed in the position indicated by a difference 
electron density map and its position was allowed to refine together with 
an isotropic displacement parameter, while the N-H distance was 
restrained to 0.88(1) Å.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0850P)²+0.5336P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   'geom & difmap'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1051 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3606
_refine_ls_number_parameters     252
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1556
_refine_ls_wR_factor_gt          0.1433
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.041

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 0.27077(10) 0.6849(6) 0.1812(3) 0.0570(8) Uani 1 1 d . . . . .
O2 O 0.40457(18) 0.5239(12) 0.8811(4) 0.115(2) Uani 1 1 d . . . . .
O3 O 0.42635(16) 0.1852(8) 0.7877(3) 0.0859(13) Uani 1 1 d . . . . .
O4 O 0.41253(9) 0.8705(5) 0.5070(2) 0.0468(6) Uani 1 1 d . . . . .
O5 O 0.43828(11) 0.5503(5) 0.3937(3) 0.0566(8) Uani 1 1 d . . . . .
N1 N 0.22059(12) 0.3809(9) 0.1982(3) 0.0579(9) Uani 1 1 d . . . . .
N2 N 0.18692(14) 0.2700(11) 0.1462(4) 0.0749(14) Uani 1 1 d . . . . .
N3 N 0.18596(13) 0.5668(9) -0.0170(3) 0.0615(10) Uani 1 1 d . . . . .
N4 N 0.21951(12) 0.6780(8) 0.0333(3) 0.0557(9) Uani 1 1 d . . . . .
N5 N 0.41516(11) 0.4514(6) 0.5704(3) 0.0421(7) Uani 1 1 d D . . . .
H5 H 0.4216(17) 0.292(4) 0.553(5) 0.065(16) Uiso 1 1 d D . . . .
C1 C 0.23593(13) 0.5730(8) 0.1368(4) 0.0459(9) Uani 1 1 d . . . . .
C2 C 0.17189(16) 0.3656(12) 0.0404(4) 0.0687(14) Uani 1 1 d . . . . .
H2 H 0.148560 0.280398 0.001690 0.082 Uiso 1 1 calc R U . . .
C3 C 0.28876(13) 0.5958(7) 0.2949(4) 0.0469(9) Uani 1 1 d . . . . .
C4 C 0.31413(14) 0.3832(8) 0.2979(4) 0.0497(9) Uani 1 1 d . . . . .
H4 H 0.319026 0.292976 0.225375 0.060 Uiso 1 1 calc R U . . .
C5 C 0.33242(14) 0.3037(7) 0.4100(4) 0.0467(9) Uani 1 1 d . . . . .
H5A H 0.349944 0.156481 0.414130 0.056 Uiso 1 1 calc R U . . .
C6 C 0.32546(12) 0.4369(7) 0.5171(4) 0.0423(9) Uani 1 1 d . . . . .
C7 C 0.30010(13) 0.6518(8) 0.5088(4) 0.0462(9) Uani 1 1 d . . . . .
H7 H 0.295316 0.745518 0.580478 0.055 Uiso 1 1 calc R U . . .
C8 C 0.28162(13) 0.7326(8) 0.3980(4) 0.0490(9) Uani 1 1 d . . . . .
H8 H 0.264232 0.880413 0.393168 0.059 Uiso 1 1 calc R U . . .
C9 C 0.34631(12) 0.3501(8) 0.6365(3) 0.0450(9) Uani 1 1 d . . . . .
H91 H 0.351111 0.160853 0.633891 0.054 Uiso 1 1 calc R U . . .
H92 H 0.328126 0.385238 0.702247 0.054 Uiso 1 1 calc R U . . .
C10 C 0.38768(13) 0.4903(7) 0.6655(3) 0.0417(9) Uani 1 1 d . . . . .
H10 H 0.381869 0.680114 0.670072 0.050 Uiso 1 1 calc R U . . .
C11 C 0.40683(13) 0.4052(9) 0.7896(4) 0.0507(10) Uani 1 1 d . . . . .
C12 C 0.4448(2) 0.0929(15) 0.9039(5) 0.093(2) Uani 1 1 d . . . . .
H121 H 0.456661 -0.079166 0.893460 0.139 Uiso 1 1 calc R U . . .
H122 H 0.423667 0.082243 0.962115 0.139 Uiso 1 1 calc R U . . .
H123 H 0.466371 0.213170 0.934848 0.139 Uiso 1 1 calc R U . . .
C13 C 0.42098(12) 0.6441(7) 0.4909(4) 0.0415(8) Uani 1 1 d . . . . .
C14 C 0.44743(17) 0.7220(8) 0.2930(4) 0.0584(12) Uani 1 1 d . . . . .
C15 C 0.40908(18) 0.8649(14) 0.2420(5) 0.0750(15) Uani 1 1 d . . . . .
H151 H 0.386449 0.741325 0.227061 0.113 Uiso 1 1 calc R U . . .
H152 H 0.414499 0.949725 0.165320 0.113 Uiso 1 1 calc R U . . .
H153 H 0.401586 0.995785 0.300679 0.113 Uiso 1 1 calc R U . . .
C16 C 0.4630(3) 0.5393(11) 0.2014(6) 0.116(3) Uani 1 1 d . . . . .
H161 H 0.485400 0.434708 0.240469 0.174 Uiso 1 1 calc R U . . .
H162 H 0.473122 0.638587 0.134217 0.174 Uiso 1 1 calc R U . . .
H163 H 0.440626 0.425195 0.169764 0.174 Uiso 1 1 calc R U . . .
C17 C 0.48143(16) 0.9098(12) 0.3384(5) 0.0683(13) Uani 1 1 d . . . . .
H171 H 0.471230 1.025466 0.399703 0.102 Uiso 1 1 calc R U . . .
H172 H 0.489824 1.012686 0.269878 0.102 Uiso 1 1 calc R U . . .
H173 H 0.505052 0.811888 0.374719 0.102 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 0.0707(19) 0.0514(17) 0.0482(17) 0.0116(13) 0.0001(14) -0.0108(15)
O2 0.143(4) 0.148(5) 0.051(2) -0.034(3) -0.016(2) 0.075(4)
O3 0.145(4) 0.071(2) 0.0404(18) 0.0054(16) 0.000(2) 0.031(3)
O4 0.0663(16) 0.0314(12) 0.0433(14) -0.0006(11) 0.0084(11) 0.0015(13)
O5 0.097(2) 0.0322(13) 0.0441(16) 0.0006(12) 0.0283(15) 0.0015(15)
N1 0.064(2) 0.067(2) 0.0429(19) 0.0109(17) 0.0033(15) -0.012(2)
N2 0.077(3) 0.098(4) 0.048(2) 0.024(2) -0.0043(19) -0.029(3)
N3 0.067(2) 0.072(3) 0.045(2) 0.0146(19) 0.0034(17) 0.007(2)
N4 0.070(2) 0.053(2) 0.0437(19) 0.0119(16) 0.0035(17) 0.0068(18)
N5 0.0584(19) 0.0312(15) 0.0379(17) -0.0010(12) 0.0114(13) 0.0017(13)
C1 0.062(2) 0.044(2) 0.0334(18) 0.0075(16) 0.0097(16) 0.0029(18)
C2 0.069(3) 0.090(4) 0.045(2) 0.018(3) -0.005(2) -0.017(3)
C3 0.059(2) 0.039(2) 0.042(2) 0.0049(16) 0.0034(17) -0.0050(18)
C4 0.068(2) 0.043(2) 0.039(2) -0.0079(17) 0.0087(17) 0.001(2)
C5 0.059(2) 0.0373(19) 0.045(2) -0.0058(16) 0.0088(17) 0.0005(16)
C6 0.051(2) 0.0347(18) 0.042(2) -0.0060(15) 0.0110(15) -0.0070(16)
C7 0.055(2) 0.0411(19) 0.043(2) -0.0103(16) 0.0098(17) -0.0028(18)
C8 0.056(2) 0.0378(19) 0.054(2) -0.0076(18) 0.0103(18) -0.0009(18)
C9 0.059(2) 0.0390(19) 0.0379(19) -0.0014(16) 0.0105(16) -0.0039(18)
C10 0.057(2) 0.0352(17) 0.0336(19) -0.0013(15) 0.0084(16) 0.0028(16)
C11 0.059(2) 0.055(2) 0.039(2) -0.0055(19) 0.0095(16) 0.002(2)
C12 0.123(5) 0.110(5) 0.045(3) 0.020(3) 0.005(3) 0.037(5)
C13 0.052(2) 0.0329(16) 0.040(2) -0.0011(14) 0.0065(15) -0.0017(15)
C14 0.097(4) 0.037(2) 0.045(2) 0.0035(18) 0.024(2) 0.000(2)
C15 0.083(3) 0.090(4) 0.050(3) 0.021(3) -0.001(2) -0.011(3)
C16 0.239(10) 0.049(3) 0.074(4) -0.003(3) 0.091(5) -0.003(4)
C17 0.070(3) 0.066(3) 0.071(3) 0.020(3) 0.018(2) -0.004(3)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.333(6) . ?
O1 C3 1.415(5) . ?
O2 C11 1.187(6) . ?
O3 C11 1.303(6) . ?
O3 C12 1.450(6) . ?
O4 C13 1.217(5) . ?
O5 C13 1.341(5) . ?
O5 C14 1.470(5) . ?
N1 C1 1.322(5) . ?
N1 N2 1.328(6) . ?
N2 C2 1.323(6) . ?
N3 C2 1.317(7) . ?
N3 N4 1.318(6) . ?
N4 C1 1.334(5) . ?
N5 C13 1.349(5) . ?
N5 C10 1.449(5) . ?
N5 H5 0.873(14) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(6) . ?
C3 C8 1.374(6) . ?
C4 C5 1.389(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.399(5) . ?
C5 H5A 0.9500 . ?
C6 C7 1.383(6) . ?
C6 C9 1.500(6) . ?
C7 C8 1.381(6) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.543(6) . ?
C9 H91 0.9900 . ?
C9 H92 0.9900 . ?
C10 C11 1.521(6) . ?
C10 H10 1.0000 . ?
C12 H121 0.9800 . ?
C12 H122 0.9800 . ?
C12 H123 0.9800 . ?
C14 C16 1.499(7) . ?
C14 C15 1.521(8) . ?
C14 C17 1.527(8) . ?
C15 H151 0.9800 . ?
C15 H152 0.9800 . ?
C15 H153 0.9800 . ?
C16 H161 0.9800 . ?
C16 H162 0.9800 . ?
C16 H163 0.9800 . ?
C17 H171 0.9800 . ?
C17 H172 0.9800 . ?
C17 H173 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C3 117.7(3) . . ?
C11 O3 C12 116.1(4) . . ?
C13 O5 C14 120.7(3) . . ?
C1 N1 N2 116.0(4) . . ?
C2 N2 N1 117.0(4) . . ?
C2 N3 N4 116.9(4) . . ?
N3 N4 C1 116.4(4) . . ?
C13 N5 C10 119.8(3) . . ?
C13 N5 H5 120(4) . . ?
C10 N5 H5 117(4) . . ?
N1 C1 O1 119.0(4) . . ?
N1 C1 N4 126.8(4) . . ?
O1 C1 N4 114.2(4) . . ?
N3 C2 N2 126.7(5) . . ?
N3 C2 H2 116.6 . . ?
N2 C2 H2 116.6 . . ?
C4 C3 C8 122.2(4) . . ?
C4 C3 O1 119.2(4) . . ?
C8 C3 O1 118.6(4) . . ?
C3 C4 C5 118.2(4) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C4 C5 C6 121.1(4) . . ?
C4 C5 H5A 119.5 . . ?
C6 C5 H5A 119.5 . . ?
C7 C6 C5 118.4(4) . . ?
C7 C6 C9 121.6(3) . . ?
C5 C6 C9 119.9(4) . . ?
C8 C7 C6 121.1(4) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C3 C8 C7 119.0(4) . . ?
C3 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C6 C9 C10 111.6(3) . . ?
C6 C9 H91 109.3 . . ?
C10 C9 H91 109.3 . . ?
C6 C9 H92 109.3 . . ?
C10 C9 H92 109.3 . . ?
H91 C9 H92 108.0 . . ?
N5 C10 C11 112.1(3) . . ?
N5 C10 C9 111.7(3) . . ?
C11 C10 C9 109.8(3) . . ?
N5 C10 H10 107.7 . . ?
C11 C10 H10 107.7 . . ?
C9 C10 H10 107.7 . . ?
O2 C11 O3 121.9(5) . . ?
O2 C11 C10 124.4(4) . . ?
O3 C11 C10 113.7(4) . . ?
O3 C12 H121 109.5 . . ?
O3 C12 H122 109.5 . . ?
H121 C12 H122 109.5 . . ?
O3 C12 H123 109.5 . . ?
H121 C12 H123 109.5 . . ?
H122 C12 H123 109.5 . . ?
O4 C13 O5 125.3(4) . . ?
O4 C13 N5 124.6(4) . . ?
O5 C13 N5 110.1(3) . . ?
O5 C14 C16 103.3(4) . . ?
O5 C14 C15 111.0(4) . . ?
C16 C14 C15 111.8(6) . . ?
O5 C14 C17 108.8(4) . . ?
C16 C14 C17 110.0(5) . . ?
C15 C14 C17 111.6(4) . . ?
C14 C15 H151 109.5 . . ?
C14 C15 H152 109.5 . . ?
H151 C15 H152 109.5 . . ?
C14 C15 H153 109.5 . . ?
H151 C15 H153 109.5 . . ?
H152 C15 H153 109.5 . . ?
C14 C16 H161 109.5 . . ?
C14 C16 H162 109.5 . . ?
H161 C16 H162 109.5 . . ?
C14 C16 H163 109.5 . . ?
H161 C16 H163 109.5 . . ?
H162 C16 H163 109.5 . . ?
C14 C17 H171 109.5 . . ?
C14 C17 H172 109.5 . . ?
H171 C17 H172 109.5 . . ?
C14 C17 H173 109.5 . . ?
H171 C17 H173 109.5 . . ?
H172 C17 H173 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
C1 N1 N2 C2 -1.2(8) . . . . ?
C2 N3 N4 C1 0.5(7) . . . . ?
N2 N1 C1 O1 -176.9(4) . . . . ?
N2 N1 C1 N4 5.2(7) . . . . ?
C3 O1 C1 N1 -2.0(6) . . . . ?
C3 O1 C1 N4 176.0(4) . . . . ?
N3 N4 C1 N1 -4.9(7) . . . . ?
N3 N4 C1 O1 177.2(4) . . . . ?
N4 N3 C2 N2 3.2(9) . . . . ?
N1 N2 C2 N3 -2.9(9) . . . . ?
C1 O1 C3 C4 85.0(5) . . . . ?
C1 O1 C3 C8 -97.9(5) . . . . ?
C8 C3 C4 C5 1.1(6) . . . . ?
O1 C3 C4 C5 178.1(4) . . . . ?
C3 C4 C5 C6 -0.4(6) . . . . ?
C4 C5 C6 C7 -0.5(6) . . . . ?
C4 C5 C6 C9 -178.7(4) . . . . ?
C5 C6 C7 C8 0.7(6) . . . . ?
C9 C6 C7 C8 178.9(4) . . . . ?
C4 C3 C8 C7 -0.9(6) . . . . ?
O1 C3 C8 C7 -178.0(4) . . . . ?
C6 C7 C8 C3 0.0(6) . . . . ?
C7 C6 C9 C10 -86.7(4) . . . . ?
C5 C6 C9 C10 91.5(4) . . . . ?
C13 N5 C10 C11 -132.2(4) . . . . ?
C13 N5 C10 C9 104.0(4) . . . . ?
C6 C9 C10 N5 -57.4(4) . . . . ?
C6 C9 C10 C11 177.6(3) . . . . ?
C12 O3 C11 O2 0.6(9) . . . . ?
C12 O3 C11 C10 -179.2(5) . . . . ?
N5 C10 C11 O2 136.9(6) . . . . ?
C9 C10 C11 O2 -98.3(6) . . . . ?
N5 C10 C11 O3 -43.3(5) . . . . ?
C9 C10 C11 O3 81.5(5) . . . . ?
C14 O5 C13 O4 -2.2(7) . . . . ?
C14 O5 C13 N5 179.4(4) . . . . ?
C10 N5 C13 O4 17.6(6) . . . . ?
C10 N5 C13 O5 -163.9(3) . . . . ?
C13 O5 C14 C16 -175.7(5) . . . . ?
C13 O5 C14 C15 -55.8(6) . . . . ?
C13 O5 C14 C17 67.4(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N5 H5 O4 0.873(14) 2.25(2) 3.078(4) 159(5) 1_545 yes


_shelx_res_file                  
;
TITL gd1902a_cu_a.res in C2
    x.res
    created by SHELXL-2018/3 at 09:55:07 on 07-Mar-2019
REM Old TITL GD1902a_Cu in C8
REM SHELXT solution in C2: R1 0.169, Rweak 0.046, Alpha 0.004
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Flack x = 0.429 ( 0.271 ) from 1113 Parsons' quotients
REM Formula found by SHELXT: C16 N2 O4
CELL 1.54184 32.663 5.161 11.0162 90 94.704 90
ZERR 4 0.002 0.0002 0.0006 0 0.005 0
LATT -7
SYMM -X,+Y,-Z
SFAC C H N O
UNIT 68 84 20 20

L.S. 8
PLAN  12
TEMP -113
BOND $H
CONF
EQIV $1 x, y-1, z
HTAB N5 O4_$1
fmap 2
acta
DFIX 0.88 0.01 N5 H5
WGHT    0.085000    0.533600
FVAR       5.07317
O1    4    0.270768    0.684869    0.181206    11.00000    0.07071    0.05137 =
         0.04821    0.01161    0.00006   -0.01078
O2    4    0.404567    0.523896    0.881113    11.00000    0.14261    0.14836 =
         0.05104   -0.03427   -0.01618    0.07458
O3    4    0.426350    0.185206    0.787664    11.00000    0.14490    0.07123 =
         0.04043    0.00542    0.00025    0.03135
O4    4    0.412533    0.870499    0.507012    11.00000    0.06628    0.03141 =
         0.04326   -0.00058    0.00842    0.00149
O5    4    0.438279    0.550302    0.393693    11.00000    0.09732    0.03218 =
         0.04406    0.00056    0.02832    0.00155
N1    3    0.220593    0.380948    0.198186    11.00000    0.06400    0.06652 =
         0.04291    0.01091    0.00327   -0.01160
N2    3    0.186917    0.269966    0.146205    11.00000    0.07670    0.09801 =
         0.04842    0.02388   -0.00428   -0.02905
N3    3    0.185955    0.566830   -0.016952    11.00000    0.06677    0.07227 =
         0.04519    0.01462    0.00343    0.00696
N4    3    0.219507    0.677959    0.033281    11.00000    0.07045    0.05270 =
         0.04369    0.01195    0.00346    0.00683
N5    3    0.415162    0.451418    0.570412    11.00000    0.05844    0.03115 =
         0.03793   -0.00105    0.01138    0.00173
H5    2    0.421554    0.292103    0.553321    11.00000    0.06500
C1    1    0.235927    0.573009    0.136783    11.00000    0.06170    0.04352 =
         0.03341    0.00748    0.00968    0.00289
C2    1    0.171894    0.365609    0.040359    11.00000    0.06880    0.09025 =
         0.04545    0.01835   -0.00478   -0.01703
AFIX  43
H2    2    0.148560    0.280398    0.001690    11.00000   -1.20000
AFIX   0
C3    1    0.288760    0.595768    0.294855    11.00000    0.05913    0.03929 =
         0.04225    0.00492    0.00344   -0.00502
C4    1    0.314126    0.383190    0.297946    11.00000    0.06815    0.04290 =
         0.03885   -0.00791    0.00872    0.00149
AFIX  43
H4    2    0.319026    0.292976    0.225375    11.00000   -1.20000
AFIX   0
C5    1    0.332422    0.303680    0.410050    11.00000    0.05905    0.03734 =
         0.04459   -0.00585    0.00882    0.00053
AFIX  43
H5A   2    0.349944    0.156481    0.414130    11.00000   -1.20000
AFIX   0
C6    1    0.325461    0.436893    0.517073    11.00000    0.05101    0.03473 =
         0.04225   -0.00605    0.01098   -0.00699
C7    1    0.300100    0.651846    0.508764    11.00000    0.05529    0.04107 =
         0.04318   -0.01029    0.00981   -0.00282
AFIX  43
H7    2    0.295316    0.745518    0.580478    11.00000   -1.20000
AFIX   0
C8    1    0.281617    0.732573    0.397991    11.00000    0.05639    0.03784 =
         0.05373   -0.00757    0.01028   -0.00086
AFIX  43
H8    2    0.264232    0.880413    0.393168    11.00000   -1.20000
AFIX   0
C9    1    0.346308    0.350094    0.636536    11.00000    0.05903    0.03900 =
         0.03791   -0.00139    0.01048   -0.00389
AFIX  23
H91   2    0.351111    0.160853    0.633891    11.00000   -1.20000
H92   2    0.328126    0.385238    0.702247    11.00000   -1.20000
AFIX   0
C10   1    0.387676    0.490274    0.665518    11.00000    0.05705    0.03516 =
         0.03363   -0.00135    0.00841    0.00279
AFIX  13
H10   2    0.381869    0.680114    0.670072    11.00000   -1.20000
AFIX   0
C11   1    0.406832    0.405246    0.789645    11.00000    0.05895    0.05533 =
         0.03862   -0.00548    0.00953    0.00165
C12   1    0.444754    0.092879    0.903947    11.00000    0.12335    0.10989 =
         0.04549    0.02016    0.00543    0.03739
AFIX 137
H121  2    0.456661   -0.079166    0.893460    11.00000   -1.50000
H122  2    0.423667    0.082243    0.962115    11.00000   -1.50000
H123  2    0.466371    0.213170    0.934848    11.00000   -1.50000
AFIX   0
C13   1    0.420976    0.644075    0.490881    11.00000    0.05239    0.03292 =
         0.03966   -0.00114    0.00647   -0.00174
C14   1    0.447435    0.721977    0.292955    11.00000    0.09668    0.03682 =
         0.04479    0.00351    0.02368   -0.00043
C15   1    0.409081    0.864914    0.241970    11.00000    0.08326    0.09045 =
         0.05031    0.02072   -0.00067   -0.01063
AFIX 137
H151  2    0.386449    0.741325    0.227061    11.00000   -1.50000
H152  2    0.414499    0.949725    0.165320    11.00000   -1.50000
H153  2    0.401586    0.995785    0.300679    11.00000   -1.50000
AFIX   0
C16   1    0.462993    0.539299    0.201426    11.00000    0.23866    0.04868 =
         0.07367   -0.00314    0.09084   -0.00278
AFIX 137
H161  2    0.485400    0.434708    0.240469    11.00000   -1.50000
H162  2    0.473122    0.638587    0.134217    11.00000   -1.50000
H163  2    0.440626    0.425195    0.169764    11.00000   -1.50000
AFIX   0
C17   1    0.481430    0.909831    0.338383    11.00000    0.06965    0.06581 =
         0.07128    0.02004    0.01784   -0.00379
AFIX 137
H171  2    0.471230    1.025466    0.399703    11.00000   -1.50000
H172  2    0.489824    1.012686    0.269878    11.00000   -1.50000
H173  2    0.505052    0.811888    0.374719    11.00000   -1.50000
AFIX   0
HKLF 4




REM  gd1902a_cu_a.res in C2
REM wR2 = 0.1556, GooF = S = 1.039, Restrained GooF = 1.039 for all data
REM R1 = 0.0541 for 2965 Fo > 4sig(Fo) and 0.0664 for all 3606 data
REM 252 parameters refined using 2 restraints

END

WGHT      0.0850      0.5339

REM Highest difference peak  0.288,  deepest hole -0.175,  1-sigma level  0.041
Q1    1   0.3865  0.3486  0.8603  11.00000  0.05    0.29
Q2    1   0.4395  0.3638  0.7837  11.00000  0.05    0.26
Q3    1   0.4085  0.5435  0.3834  11.00000  0.05    0.20
Q4    1   0.4178  0.5034  0.1638  11.00000  0.05    0.20
Q5    1   0.2865  0.4164  0.3029  11.00000  0.05    0.19
Q6    1   0.2992  0.4605  0.5168  11.00000  0.05    0.18
Q7    1   0.3983  0.2265  0.8122  11.00000  0.05    0.18
Q8    1   0.3293  0.6296  0.5085  11.00000  0.05    0.17
Q9    1   0.4135  0.7264  0.2751  11.00000  0.05    0.15
Q10   1   0.2992  0.6857  0.1817  11.00000  0.05    0.15
Q11   1   0.4456  0.4668  0.5846  11.00000  0.05    0.15
Q12   1   0.3175  0.5933  0.2999  11.00000  0.05    0.15
;
_shelx_res_checksum              40968

#   End of CIF   ============================================================
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether'
