# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_atz-fum_h2o
_database_code_depnum_ccdc_archive 'CCDC 2046236'
loop_
_audit_author_name
_audit_author_address
'Paulo S. Carvalho Jr.'
;Federal University of Mato Grosso do Sul
Brazil
;
_audit_update_record             
;
2020-11-24 deposited with the CCDC.	2021-05-10 downloaded from the CCDC.
;
_audit_creation_date             2020-11-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        'Atrazine fumaric acid cocrystal'
_chemical_formula_moiety         'C8 H14 Cl N5, C2 H2 O2, 0.11(H2 O)'
_chemical_formula_sum            'C10 H16.22 Cl N5 O2.11'
_chemical_formula_weight         275.71
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   18.892(4)
_cell_length_b                   6.2547(15)
_cell_length_c                   24.173(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.589(4)
_cell_angle_gamma                90
_cell_volume                     2764.3(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    28552
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.730
_cell_measurement_theta_min      3.155
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.940
_exptl_absorpt_coefficient_mu    0.281
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1161
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2164
_diffrn_reflns_av_unetI/netI     0.0811
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            28552
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.730
_diffrn_reflns_theta_min         3.155
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2470
_reflns_number_total             2928
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.658
_refine_diff_density_min         -0.892
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2928
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0863
_refine_ls_restrained_S_all      1.161
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0452P)²+19.1131P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2048
_refine_ls_wR_factor_ref         0.2128
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Rigid body (RIGU) restrains
 N4, N1, C2, C3, C1, N3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Fixed Sof: OW1(0.11) HW1A(0.11) HW1B(0.11)
4.a Free rotating group:
 OW1(HW1A,HW1B)
4.b Ternary CH refined with riding coordinates:
 C6(H6)
4.c Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
4.d Aromatic/amide H refined with riding coordinates:
 N2(H2), N5(H5), C10(H10)
4.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C5(H5A,H5B,H5C)
4.f Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.84074(5) 0.58752(15) 0.82621(4) 0.0217(3) Uani 1 1 d . . . . .
O2 O 0.58318(14) 0.5886(5) 0.68217(12) 0.0246(6) Uani 1 1 d . . . . .
O1 O 0.65983(13) 0.6004(5) 0.76998(11) 0.0224(6) Uani 1 1 d . . . . .
H1 H 0.6920 0.6022 0.7516 0.034 Uiso 1 1 calc R U . . .
N3 N 0.83008(16) 0.6091(5) 0.64261(13) 0.0202(7) Uani 1 1 d . U . . .
N4 N 0.90065(16) 0.6024(5) 0.74090(13) 0.0181(6) Uani 1 1 d . U . . .
N2 N 0.70412(16) 0.5890(5) 0.62634(13) 0.0216(7) Uani 1 1 d . . . . .
H2 H 0.6660 0.5755 0.6407 0.026 Uiso 1 1 calc R U . . .
N5 N 0.95632(17) 0.6264(5) 0.66715(14) 0.0218(7) Uani 1 1 d . . . . .
H5 H 0.9975 0.6248 0.6941 0.026 Uiso 1 1 calc R U . . .
N1 N 0.77066(16) 0.5926(5) 0.71965(13) 0.0182(6) Uani 1 1 d . U . . .
C2 C 0.76989(19) 0.5980(6) 0.66272(16) 0.0192(7) Uani 1 1 d . U . . .
C9 C 0.59426(19) 0.5972(6) 0.73388(16) 0.0200(7) Uani 1 1 d . . . . .
C3 C 0.8935(2) 0.6110(6) 0.68292(16) 0.0189(7) Uani 1 1 d . U . . .
C1 C 0.83722(19) 0.5961(6) 0.75369(15) 0.0175(7) Uani 1 1 d . U . . .
C6 C 0.6907(2) 0.5999(7) 0.56411(16) 0.0263(8) Uani 1 1 d . . . . .
H6 H 0.7316 0.5253 0.5526 0.032 Uiso 1 1 calc R U . . .
C4 C 0.9603(2) 0.6455(7) 0.60804(17) 0.0271(9) Uani 1 1 d . . . . .
H4A H 1.0050 0.7259 0.6068 0.032 Uiso 1 1 calc R U . . .
H4B H 0.9176 0.7282 0.5863 0.032 Uiso 1 1 calc R U . . .
C10 C 0.5347(2) 0.5997(6) 0.76448(17) 0.0213(8) Uani 1 1 d . . . . .
H10 H 0.5469 0.6013 0.8051 0.026 Uiso 1 1 calc R U . . .
C7 C 0.6881(3) 0.8315(8) 0.5438(2) 0.0366(10) Uani 1 1 d . . . . .
H7A H 0.6466 0.9047 0.5529 0.055 Uiso 1 1 calc R U . . .
H7B H 0.6824 0.8345 0.5023 0.055 Uiso 1 1 calc R U . . .
H7C H 0.7337 0.9040 0.5630 0.055 Uiso 1 1 calc R U . . .
C8 C 0.6195(3) 0.4821(8) 0.5374(2) 0.0389(11) Uani 1 1 d . . . . .
H8A H 0.6237 0.3328 0.5501 0.058 Uiso 1 1 calc R U . . .
H8B H 0.6099 0.4871 0.4956 0.058 Uiso 1 1 calc R U . . .
H8C H 0.5790 0.5507 0.5493 0.058 Uiso 1 1 calc R U . . .
C5 C 0.9615(3) 0.4312(9) 0.5799(2) 0.0423(12) Uani 1 1 d . . . . .
H5A H 0.9662 0.4519 0.5408 0.063 Uiso 1 1 calc R U . . .
H5B H 0.9160 0.3545 0.5788 0.063 Uiso 1 1 calc R U . . .
H5C H 1.0031 0.3476 0.6016 0.063 Uiso 1 1 calc R U . . .
OW1 O 0.8265(19) 1.128(4) 0.6014(14) 0.039(7) Uani 0.11 1 d G . P . .
HW1A H 0.8196 1.1845 0.5685 0.058 Uiso 0.11 1 d G U P . .
HW1B H 0.8398 0.9991 0.6001 0.058 Uiso 0.11 1 d G U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.738(4) . ?
O2 C9 1.215(5) . ?
O1 H1 0.8400 . ?
O1 C9 1.324(5) . ?
N3 C2 1.346(4) . ?
N3 C3 1.341(5) . ?
N4 C3 1.375(5) . ?
N4 C1 1.311(4) . ?
N2 H2 0.8800 . ?
N2 C2 1.330(5) . ?
N2 C6 1.463(5) . ?
N5 H5 0.8800 . ?
N5 C3 1.338(4) . ?
N5 C4 1.455(5) . ?
N1 C2 1.373(5) . ?
N1 C1 1.318(5) . ?
C9 C10 1.494(5) . ?
C6 H6 1.0000 . ?
C6 C7 1.527(6) . ?
C6 C8 1.528(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.507(6) . ?
C10 C10 1.323(8) 2_656 ?
C10 H10 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
OW1 HW1A 0.8495 . ?
OW1 HW1B 0.8496 . ?

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
C9 O1 H1 109.5 . . ?
C3 N3 C2 114.8(3) . . ?
C1 N4 C3 112.4(3) . . ?
C2 N2 H2 117.7 . . ?
C2 N2 C6 124.7(3) . . ?
C6 N2 H2 117.7 . . ?
C3 N5 H5 118.1 . . ?
C3 N5 C4 123.7(3) . . ?
C4 N5 H5 118.1 . . ?
C1 N1 C2 113.1(3) . . ?
N3 C2 N1 124.5(3) . . ?
N2 C2 N3 119.8(3) . . ?
N2 C2 N1 115.7(3) . . ?
O2 C9 O1 124.7(3) . . ?
O2 C9 C10 123.6(3) . . ?
O1 C9 C10 111.7(3) . . ?
N3 C3 N4 125.5(3) . . ?
N5 C3 N3 119.2(3) . . ?
N5 C3 N4 115.3(3) . . ?
N4 C1 Cl1 115.7(3) . . ?
N4 C1 N1 129.6(3) . . ?
N1 C1 Cl1 114.7(2) . . ?
N2 C6 H6 108.5 . . ?
N2 C6 C7 111.0(3) . . ?
N2 C6 C8 108.6(3) . . ?
C7 C6 H6 108.5 . . ?
C7 C6 C8 111.6(4) . . ?
C8 C6 H6 108.5 . . ?
N5 C4 H4A 109.1 . . ?
N5 C4 H4B 109.1 . . ?
N5 C4 C5 112.4(3) . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C9 C10 H10 119.7 . . ?
C10 C10 C9 120.6(5) 2_656 . ?
C10 C10 H10 119.7 2_656 . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
HW1A OW1 HW1B 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
O2 C9 C10 C10 -2.3(4) . . . 2_656 ?
O1 C9 C10 C10 179.17(19) . . . 2_656 ?
C2 N3 C3 N4 0.1(5) . . . . ?
C2 N3 C3 N5 -178.6(3) . . . . ?
C2 N2 C6 C7 -83.8(5) . . . . ?
C2 N2 C6 C8 153.1(4) . . . . ?
C2 N1 C1 Cl1 -179.5(2) . . . . ?
C2 N1 C1 N4 -0.5(5) . . . . ?
C3 N3 C2 N2 -178.1(3) . . . . ?
C3 N3 C2 N1 1.1(5) . . . . ?
C3 N4 C1 Cl1 -179.4(2) . . . . ?
C3 N4 C1 N1 1.5(5) . . . . ?
C3 N5 C4 C5 -87.7(5) . . . . ?
C1 N4 C3 N3 -1.3(5) . . . . ?
C1 N4 C3 N5 177.4(3) . . . . ?
C1 N1 C2 N3 -1.0(5) . . . . ?
C1 N1 C2 N2 178.3(3) . . . . ?
C6 N2 C2 N3 -2.9(6) . . . . ?
C6 N2 C2 N1 177.8(3) . . . . ?
C4 N5 C3 N3 1.2(5) . . . . ?
C4 N5 C3 N4 -177.6(3) . . . . ?



# start Validation Reply Form

_vrf_RINTA01_atz-fum_h2o         
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: This large value is due to poor quality of the ATZ-Fum H2O crystals.
The coixistence of isostructural hydrate and dehydrated phases
 have identified as outcome of the crystallization.
 Notably, the ATZ-Fum H2O structure showed poor thermal stability,
 releasing the water molecules below 330 K converting into the isostructural
 dehydrate. This type of hydrate occurs owing to the structure formed
 be able to generate channels that allow the flow of water
 molecules with low retention
;
_vrf_PLAT020_atz-fum_h2o         
;
PROBLEM: The Value of Rint is Greater Than 0.12 ......... 0.261 Report
RESPONSE: This large value is due to poor quality of the ATZ-Fum H2O crystals.
The coixistence of isostructural hydrate and dehydrated phases
 have identified as outcome of the crystallization.
 Notably, the ATZ-Fum H2O structure showed poor thermal stability,
 releasing the water molecules below 330 K converting into the isostructural
 dehydrate. This type of hydrate occurs owing to the structure formed
 be able to generate channels that allow the flow of water
 molecules with low retention
;
_vrf_PLAT340_atz-fum_h2o         
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.0064 Ang.
RESPONSE: This large value is due to poor quality of the ATZ-Fum H2O crystals.
The coixistence of isostructural hydrate and dehydrated phases
 have identified as outcome of the crystallization.
 Notably, the ATZ-Fum H2O structure showed poor thermal stability,
 releasing the water molecules below 330 K converting into the isostructural
 dehydrate. This type of hydrate occurs owing to the structure formed
 be able to generate channels that allow the flow of water
 molecules with low retention;
;
####################################################################### 
# 
# 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_amt_no3
_database_code_depnum_ccdc_archive 'CCDC 2046238'
loop_
_audit_author_name
_audit_author_address
'Paulo S. Carvalho Jr.'
;Federal University of Mato Grosso do Sul
Brazil
;
_audit_update_record             
;
2020-11-24 deposited with the CCDC.	2021-05-10 downloaded from the CCDC.
;
_audit_creation_date             2020-11-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H18 N5 S, N O3'
_chemical_formula_sum            'C9 H18 N6 O3 S'
_chemical_formula_weight         290.35
_chemical_melting_point          ?
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'

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

_cell_length_a                   9.1659(7)
_cell_length_b                   9.5067(8)
_cell_length_c                   9.6825(8)
_cell_angle_alpha                77.541(7)
_cell_angle_beta                 72.346(7)
_cell_angle_gamma                67.479(7)
_cell_volume                     737.90(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15139
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.719
_cell_measurement_theta_min      3.401
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             308
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15139
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.719
_diffrn_reflns_theta_min         3.401
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2250
_reflns_number_total             3125
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3125
_refine_ls_number_restraints     58
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0657
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0828P)²+0.3629P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1805
_refine_ls_wR_factor_ref         0.1950
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C4A-C5A
 1.51 with sigma of 0.02
 C4A-C5A \\sim C5B-C4B
 with sigma of 0.02
 N5B-C4A \\sim N5A-C4B
 with sigma of 0.02
 N5A-C3 \\sim N5B-C3
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 N5B, C4A, C5A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N5A, C5B, C4B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 N4, C1, N1, C2, N3, C3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: N5A(0.45) H5A(0.45) C5A(0.55) H5AA(0.55) H5AB(0.55) H5AC(0.55)
 C5B(0.45) H5BA(0.45) H5BB(0.45) H5BC(0.45) C4A(0.55) H4AA(0.55) H4AB(0.55)
 C4B(0.45) H4BA(0.45) H4BB(0.45) N5B(0.55) H5B(0.55)
5.a Ternary CH refined with riding coordinates:
 C6(H6)
5.b Secondary CH2 refined with riding coordinates:
 C4A(H4AA,H4AB), C4B(H4BA,H4BB)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N5A(H5A), N5B(H5B)
5.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C8(H8A,H8B,H8C), C7(H7A,H7B,H7C), C5A(H5AA,H5AB,H5AC),
 C5B(H5BA,H5BB,H5BC)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.17561(11) 0.36466(11) 0.87034(8) 0.0909(4) Uani 1 1 d . . . . .
N1 N 0.2143(3) 0.4761(2) 0.5962(2) 0.0640(6) Uani 1 1 d . U . . .
H1 H 0.1196 0.5420 0.6263 0.077 Uiso 1 1 calc R U . . .
N4 N 0.4188(3) 0.2517(2) 0.6472(2) 0.0686(6) Uani 1 1 d . U . . .
N6 N -0.1549(3) 0.7911(3) 0.6237(3) 0.0762(7) Uani 1 1 d . . . . .
N3 N 0.4383(3) 0.3855(2) 0.4044(2) 0.0697(6) Uani 1 1 d . U . . .
O1 O -0.0836(3) 0.6870(3) 0.7046(3) 0.1093(9) Uani 1 1 d . . . . .
O3 O -0.2846(3) 0.8856(3) 0.6742(3) 0.1122(10) Uani 1 1 d . . . . .
N2 N 0.2330(3) 0.6098(3) 0.3684(3) 0.0732(7) Uani 1 1 d . . . . .
H2 H 0.1392 0.6736 0.4047 0.088 Uiso 1 1 calc R U . . .
C2 C 0.2975(3) 0.4889(3) 0.4543(3) 0.0597(6) Uani 1 1 d . U . . .
C1 C 0.2825(3) 0.3586(3) 0.6892(3) 0.0611(6) Uani 1 1 d . U . . .
O2 O -0.0958(4) 0.7983(4) 0.4936(3) 0.1453(14) Uani 1 1 d . . . . .
C3 C 0.4898(4) 0.2661(3) 0.5010(3) 0.0723(8) Uani 1 1 d D U . . .
N5A N 0.5994(10) 0.1332(10) 0.4523(10) 0.0586(19) Uani 0.45 1 d D U P A 2
H5A H 0.6184 0.0531 0.5148 0.070 Uiso 0.45 1 calc R U P A 2
C6 C 0.3104(4) 0.6428(3) 0.2150(3) 0.0778(8) Uani 1 1 d . . . . .
H6 H 0.4274 0.6139 0.2059 0.093 Uiso 1 1 calc R U . . .
C9 C 0.3013(6) 0.1962(5) 0.9559(4) 0.1094(13) Uani 1 1 d . . . . .
H9A H 0.3045 0.1076 0.9211 0.164 Uiso 1 1 calc R U . . .
H9B H 0.2576 0.1908 1.0596 0.164 Uiso 1 1 calc R U . . .
H9C H 0.4096 0.1994 0.9330 0.164 Uiso 1 1 calc R U . . .
C8 C 0.2443(6) 0.8131(4) 0.1725(5) 0.1253(16) Uani 1 1 d . . . . .
H8A H 0.1293 0.8445 0.1817 0.188 Uiso 1 1 calc R U . . .
H8B H 0.2977 0.8374 0.0733 0.188 Uiso 1 1 calc R U . . .
H8C H 0.2638 0.8659 0.2354 0.188 Uiso 1 1 calc R U . . .
C7 C 0.2893(5) 0.5525(5) 0.1206(4) 0.1102(13) Uani 1 1 d . . . . .
H7A H 0.3383 0.4452 0.1492 0.165 Uiso 1 1 calc R U . . .
H7B H 0.3407 0.5775 0.0208 0.165 Uiso 1 1 calc R U . . .
H7C H 0.1753 0.5760 0.1303 0.165 Uiso 1 1 calc R U . . .
C5A C 0.7222(17) 0.0711(14) 0.2379(11) 0.154(4) Uani 0.55 1 d D U P A 1
H5AA H 0.7969 0.0584 0.1437 0.231 Uiso 0.55 1 calc R U P A 1
H5AB H 0.6126 0.1165 0.2266 0.231 Uiso 0.55 1 calc R U P A 1
H5AC H 0.7358 -0.0271 0.2949 0.231 Uiso 0.55 1 calc R U P A 1
C5B C 0.8343(10) 0.1684(11) 0.2432(10) 0.092(3) Uani 0.45 1 d D U P A 2
H5BA H 0.8880 0.1420 0.1457 0.138 Uiso 0.45 1 calc R U P A 2
H5BB H 0.9082 0.1182 0.3051 0.138 Uiso 0.45 1 calc R U P A 2
H5BC H 0.7999 0.2774 0.2429 0.138 Uiso 0.45 1 calc R U P A 2
C4A C 0.7548(13) 0.1706(10) 0.3119(9) 0.111(3) Uani 0.55 1 d D U P A 1
H4AA H 0.7314 0.2736 0.2613 0.133 Uiso 0.55 1 calc R U P A 1
H4AB H 0.8675 0.1309 0.3178 0.133 Uiso 0.55 1 calc R U P A 1
C4B C 0.6876(8) 0.1175(9) 0.2996(7) 0.0604(15) Uani 0.45 1 d D U P A 2
H4BA H 0.6114 0.1751 0.2396 0.073 Uiso 0.45 1 calc R U P A 2
H4BB H 0.7229 0.0105 0.2852 0.073 Uiso 0.45 1 calc R U P A 2
N5B N 0.6420(9) 0.1691(10) 0.4608(9) 0.085(3) Uani 0.55 1 d D U P A 1
H5B H 0.6787 0.0992 0.5268 0.102 Uiso 0.55 1 calc R U P A 1


_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 C1 1.732(3) . ?
S1 C9 1.781(4) . ?
N1 H1 0.8600 . ?
N1 C2 1.359(3) . ?
N1 C1 1.349(3) . ?
N4 C1 1.288(3) . ?
N4 C3 1.368(3) . ?
N6 O1 1.226(3) . ?
N6 O3 1.216(3) . ?
N6 O2 1.210(3) . ?
N3 C2 1.311(3) . ?
N3 C3 1.336(3) . ?
N2 H2 0.8600 . ?
N2 C2 1.315(3) . ?
N2 C6 1.462(4) . ?
C3 N5A 1.351(8) . ?
C3 N5B 1.337(8) . ?
N5A H5A 0.8600 . ?
N5A C4B 1.463(9) . ?
C6 H6 0.9800 . ?
C6 C8 1.507(4) . ?
C6 C7 1.478(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C5A H5AA 0.9600 . ?
C5A H5AB 0.9600 . ?
C5A H5AC 0.9600 . ?
C5A C4A 1.461(10) . ?
C5B H5BA 0.9600 . ?
C5B H5BB 0.9600 . ?
C5B H5BC 0.9600 . ?
C5B C4B 1.510(10) . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C4A N5B 1.499(10) . ?
C4B H4BA 0.9700 . ?
C4B H4BB 0.9700 . ?
N5B H5B 0.8600 . ?

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 S1 C9 101.78(16) . . ?
C2 N1 H1 120.5 . . ?
C1 N1 H1 120.5 . . ?
C1 N1 C2 119.0(2) . . ?
C1 N4 C3 114.9(2) . . ?
O3 N6 O1 120.0(3) . . ?
O2 N6 O1 119.5(3) . . ?
O2 N6 O3 120.5(3) . . ?
C2 N3 C3 115.4(2) . . ?
C2 N2 H2 117.9 . . ?
C2 N2 C6 124.2(2) . . ?
C6 N2 H2 117.9 . . ?
N3 C2 N1 121.5(2) . . ?
N3 C2 N2 120.8(2) . . ?
N2 C2 N1 117.7(2) . . ?
N1 C1 S1 115.03(19) . . ?
N4 C1 S1 122.3(2) . . ?
N4 C1 N1 122.7(2) . . ?
N3 C3 N4 126.0(2) . . ?
N3 C3 N5A 119.2(5) . . ?
N3 C3 N5B 117.2(5) . . ?
N5A C3 N4 113.4(5) . . ?
N5B C3 N4 114.9(4) . . ?
C3 N5A H5A 118.1 . . ?
C3 N5A C4B 123.9(8) . . ?
C4B N5A H5A 118.1 . . ?
N2 C6 H6 107.9 . . ?
N2 C6 C8 108.4(3) . . ?
N2 C6 C7 111.7(3) . . ?
C8 C6 H6 107.9 . . ?
C7 C6 H6 107.9 . . ?
C7 C6 C8 113.0(3) . . ?
S1 C9 H9A 109.5 . . ?
S1 C9 H9B 109.5 . . ?
S1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
H5AA C5A H5AB 109.5 . . ?
H5AA C5A H5AC 109.5 . . ?
H5AB C5A H5AC 109.5 . . ?
C4A C5A H5AA 109.5 . . ?
C4A C5A H5AB 109.5 . . ?
C4A C5A H5AC 109.5 . . ?
H5BA C5B H5BB 109.5 . . ?
H5BA C5B H5BC 109.5 . . ?
H5BB C5B H5BC 109.5 . . ?
C4B C5B H5BA 109.5 . . ?
C4B C5B H5BB 109.5 . . ?
C4B C5B H5BC 109.5 . . ?
C5A C4A H4AA 110.9 . . ?
C5A C4A H4AB 110.9 . . ?
C5A C4A N5B 104.1(10) . . ?
H4AA C4A H4AB 109.0 . . ?
N5B C4A H4AA 110.9 . . ?
N5B C4A H4AB 110.9 . . ?
N5A C4B C5B 117.6(7) . . ?
N5A C4B H4BA 107.9 . . ?
N5A C4B H4BB 107.9 . . ?
C5B C4B H4BA 107.9 . . ?
C5B C4B H4BB 107.9 . . ?
H4BA C4B H4BB 107.2 . . ?
C3 N5B C4A 126.3(8) . . ?
C3 N5B H5B 116.8 . . ?
C4A N5B H5B 116.8 . . ?

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 C3 N5A C4B 177.9(6) . . . . ?
N4 C3 N5B C4A -172.8(7) . . . . ?
N3 C3 N5A C4B 10.8(9) . . . . ?
N3 C3 N5B C4A -7.6(10) . . . . ?
C2 N1 C1 S1 173.7(2) . . . . ?
C2 N1 C1 N4 -4.8(4) . . . . ?
C2 N3 C3 N4 -7.7(5) . . . . ?
C2 N3 C3 N5A 157.7(4) . . . . ?
C2 N3 C3 N5B -171.0(4) . . . . ?
C2 N2 C6 C8 -155.2(3) . . . . ?
C2 N2 C6 C7 79.7(4) . . . . ?
C1 N1 C2 N3 3.6(4) . . . . ?
C1 N1 C2 N2 -175.6(2) . . . . ?
C1 N4 C3 N3 6.5(5) . . . . ?
C1 N4 C3 N5A -159.6(4) . . . . ?
C1 N4 C3 N5B 170.2(4) . . . . ?
C3 N4 C1 S1 -178.3(2) . . . . ?
C3 N4 C1 N1 0.1(4) . . . . ?
C3 N3 C2 N1 2.3(4) . . . . ?
C3 N3 C2 N2 -178.6(3) . . . . ?
C3 N5A C4B C5B 80.3(9) . . . . ?
C6 N2 C2 N1 177.5(3) . . . . ?
C6 N2 C2 N3 -1.7(5) . . . . ?
C9 S1 C1 N1 -179.7(2) . . . . ?
C9 S1 C1 N4 -1.2(3) . . . . ?
C5A C4A N5B C3 -90.3(10) . . . . ?


_olex2_submission_original_sample_id 'Ametryn nitrate'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_amt_3fac
_database_code_depnum_ccdc_archive 'CCDC 2046239'
loop_
_audit_author_name
_audit_author_address
'Paulo S. Carvalho Jr.'
;Federal University of Mato Grosso do Sul
Brazil
;
_audit_update_record             
;
2020-11-24 deposited with the CCDC.	2021-05-10 downloaded from the CCDC.
;
_audit_creation_date             2020-11-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H18 N5 S, C2 F3 O2'
_chemical_formula_sum            'C11 H18 F3 N5 O2 S'
_chemical_formula_weight         341.36
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

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

_cell_length_a                   8.2238(3)
_cell_length_b                   10.1689(3)
_cell_length_c                   19.8066(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.017(3)
_cell_angle_gamma                90
_cell_volume                     1635.90(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    20777
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.484
_cell_measurement_theta_min      3.494
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.922
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20777
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.494
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2618
_reflns_number_total             3703
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.923
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3703
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0711
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1223P)²+1.1226P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2156
_refine_ls_wR_factor_ref         0.2365
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N5(H5)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C7(H7A,H7B,H7C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.82545(11) 0.41825(10) 0.46050(4) 0.0657(3) Uani 1 1 d . . . . .
O2 O 0.5008(3) 0.3532(3) 0.67362(12) 0.0736(7) Uani 1 1 d . . . . .
N3 N 0.3524(3) 0.1996(3) 0.42864(12) 0.0531(6) Uani 1 1 d . . . . .
N1 N 0.5556(3) 0.3254(3) 0.49584(12) 0.0544(6) Uani 1 1 d . . . . .
H1 H 0.5913 0.3634 0.5341 0.065 Uiso 1 1 calc R U . . .
F1 F 0.8373(4) 0.5569(3) 0.72119(13) 0.1103(10) Uani 1 1 d . . . . .
O1 O 0.6789(4) 0.4406(3) 0.61228(12) 0.0872(9) Uani 1 1 d . . . . .
N4 N 0.5853(3) 0.2874(3) 0.38222(12) 0.0535(6) Uani 1 1 d . . . . .
N2 N 0.3413(3) 0.2374(3) 0.54190(13) 0.0584(7) Uani 1 1 d . . . . .
H2 H 0.3823 0.2762 0.5793 0.070 Uiso 1 1 calc R U . . .
N5 N 0.3812(3) 0.1726(3) 0.31632(13) 0.0638(7) Uani 1 1 d . . . . .
H5 H 0.4361 0.1882 0.2836 0.077 Uiso 1 1 calc R U . . .
C2 C 0.4142(4) 0.2536(3) 0.48763(14) 0.0494(7) Uani 1 1 d . . . . .
C1 C 0.6388(4) 0.3354(3) 0.44206(14) 0.0499(7) Uani 1 1 d . . . . .
C3 C 0.4391(4) 0.2206(3) 0.37728(15) 0.0518(7) Uani 1 1 d . . . . .
F2 F 0.6322(5) 0.5392(4) 0.76747(16) 0.1400(15) Uani 1 1 d . . . . .
C10 C 0.6246(4) 0.4151(3) 0.66530(16) 0.0595(8) Uani 1 1 d . . . . .
F3 F 0.7865(6) 0.3814(4) 0.77241(19) 0.174(2) Uani 1 1 d . . . . .
C6 C 0.1938(4) 0.1565(4) 0.54132(17) 0.0628(8) Uani 1 1 d . . . . .
H6 H 0.1214 0.1696 0.4976 0.075 Uiso 1 1 calc R U . . .
C11 C 0.7288(5) 0.4689(5) 0.73025(18) 0.0805(12) Uani 1 1 d . . . . .
C4 C 0.2313(5) 0.0952(4) 0.30039(19) 0.0726(10) Uani 1 1 d . . . . .
H4A H 0.1864 0.1068 0.2525 0.087 Uiso 1 1 calc R U . . .
H4B H 0.1506 0.1276 0.3272 0.087 Uiso 1 1 calc R U . . .
C8 C 0.2408(6) 0.0128(4) 0.5478(2) 0.0872(12) Uani 1 1 d . . . . .
H8A H 0.2912 -0.0130 0.5093 0.131 Uiso 1 1 calc R U . . .
H8B H 0.1439 -0.0392 0.5490 0.131 Uiso 1 1 calc R U . . .
H8C H 0.3170 -0.0006 0.5891 0.131 Uiso 1 1 calc R U . . .
C9 C 0.9026(6) 0.4008(6) 0.3820(2) 0.1017(17) Uani 1 1 d . . . . .
H9A H 0.8262 0.4391 0.3457 0.153 Uiso 1 1 calc R U . . .
H9B H 0.9164 0.3092 0.3727 0.153 Uiso 1 1 calc R U . . .
H9C H 1.0068 0.4448 0.3851 0.153 Uiso 1 1 calc R U . . .
C7 C 0.1044(6) 0.2003(5) 0.5979(2) 0.0930(13) Uani 1 1 d . . . . .
H7A H 0.1768 0.1942 0.6408 0.139 Uiso 1 1 calc R U . . .
H7B H 0.0103 0.1449 0.5989 0.139 Uiso 1 1 calc R U . . .
H7C H 0.0690 0.2897 0.5901 0.139 Uiso 1 1 calc R U . . .
C5 C 0.2588(6) -0.0477(5) 0.3145(3) 0.0997(15) Uani 1 1 d . . . . .
H5A H 0.3309 -0.0823 0.2851 0.150 Uiso 1 1 calc R U . . .
H5B H 0.1553 -0.0932 0.3062 0.150 Uiso 1 1 calc R U . . .
H5C H 0.3080 -0.0596 0.3614 0.150 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.739(3) . ?
S1 C9 1.779(4) . ?
O2 C10 1.229(4) . ?
N3 C2 1.319(4) . ?
N3 C3 1.348(4) . ?
N1 H1 0.8600 . ?
N1 C2 1.361(4) . ?
N1 C1 1.357(4) . ?
F1 C11 1.295(5) . ?
O1 C10 1.232(4) . ?
N4 C1 1.293(4) . ?
N4 C3 1.371(4) . ?
N2 H2 0.8600 . ?
N2 C2 1.321(4) . ?
N2 C6 1.464(4) . ?
N5 H5 0.8600 . ?
N5 C3 1.320(4) . ?
N5 C4 1.455(5) . ?
F2 C11 1.367(6) . ?
C10 C11 1.531(5) . ?
F3 C11 1.261(6) . ?
C6 H6 0.9800 . ?
C6 C8 1.511(6) . ?
C6 C7 1.500(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.490(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C9 101.08(19) . . ?
C2 N3 C3 115.2(3) . . ?
C2 N1 H1 120.9 . . ?
C1 N1 H1 120.9 . . ?
C1 N1 C2 118.2(2) . . ?
C1 N4 C3 114.9(3) . . ?
C2 N2 H2 118.5 . . ?
C2 N2 C6 123.0(3) . . ?
C6 N2 H2 118.5 . . ?
C3 N5 H5 117.6 . . ?
C3 N5 C4 124.8(3) . . ?
C4 N5 H5 117.6 . . ?
N3 C2 N1 122.2(3) . . ?
N3 C2 N2 120.5(3) . . ?
N2 C2 N1 117.3(3) . . ?
N1 C1 S1 114.1(2) . . ?
N4 C1 S1 122.5(2) . . ?
N4 C1 N1 123.4(3) . . ?
N3 C3 N4 125.9(3) . . ?
N5 C3 N3 118.3(3) . . ?
N5 C3 N4 115.8(3) . . ?
O2 C10 O1 129.8(3) . . ?
O2 C10 C11 115.9(3) . . ?
O1 C10 C11 114.3(3) . . ?
N2 C6 H6 108.5 . . ?
N2 C6 C8 110.0(3) . . ?
N2 C6 C7 109.2(3) . . ?
C8 C6 H6 108.5 . . ?
C7 C6 H6 108.5 . . ?
C7 C6 C8 111.9(3) . . ?
F1 C11 F2 100.6(4) . . ?
F1 C11 C10 116.0(3) . . ?
F2 C11 C10 110.1(3) . . ?
F3 C11 F1 112.5(4) . . ?
F3 C11 F2 101.7(4) . . ?
F3 C11 C10 114.0(4) . . ?
N5 C4 H4A 109.0 . . ?
N5 C4 H4B 109.0 . . ?
N5 C4 C5 112.8(3) . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
S1 C9 H9A 109.5 . . ?
S1 C9 H9B 109.5 . . ?
S1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 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
O2 C10 C11 F1 -165.6(4) . . . . ?
O2 C10 C11 F2 -52.2(5) . . . . ?
O2 C10 C11 F3 61.3(5) . . . . ?
O1 C10 C11 F1 14.7(6) . . . . ?
O1 C10 C11 F2 128.0(4) . . . . ?
O1 C10 C11 F3 -118.5(5) . . . . ?
C2 N3 C3 N4 2.6(5) . . . . ?
C2 N3 C3 N5 -178.0(3) . . . . ?
C2 N1 C1 S1 -175.2(2) . . . . ?
C2 N1 C1 N4 4.6(5) . . . . ?
C2 N2 C6 C8 79.8(4) . . . . ?
C2 N2 C6 C7 -157.1(3) . . . . ?
C1 N1 C2 N3 -3.4(5) . . . . ?
C1 N1 C2 N2 175.4(3) . . . . ?
C1 N4 C3 N3 -1.5(5) . . . . ?
C1 N4 C3 N5 179.0(3) . . . . ?
C3 N3 C2 N1 0.0(4) . . . . ?
C3 N3 C2 N2 -178.7(3) . . . . ?
C3 N4 C1 S1 177.5(2) . . . . ?
C3 N4 C1 N1 -2.3(4) . . . . ?
C3 N5 C4 C5 -85.8(5) . . . . ?
C6 N2 C2 N3 2.3(5) . . . . ?
C6 N2 C2 N1 -176.5(3) . . . . ?
C4 N5 C3 N3 -1.6(5) . . . . ?
C4 N5 C3 N4 178.0(3) . . . . ?
C9 S1 C1 N1 175.9(3) . . . . ?
C9 S1 C1 N4 -3.9(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_atz-fum
_database_code_depnum_ccdc_archive 'CCDC 2046237'
loop_
_audit_author_name
_audit_author_address
'Paulo S. Carvalho Jr.'
;Federal University of Mato Grosso do Sul
Brazil
;
_audit_update_record             
;
2020-11-24 deposited with the CCDC.	2021-05-10 downloaded from the CCDC.
;
_audit_creation_date             2020-11-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        'Atrazine Fumaric acid cocrystal (dehydrate)'
_chemical_formula_moiety         'C8 H14 Cl N5, C2 H2 O2'
_chemical_formula_sum            'C10 H16 Cl N5 O2'
_chemical_formula_weight         273.73
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   18.922(13)
_cell_length_b                   6.297(4)
_cell_length_c                   24.311(16)
_cell_angle_alpha                90
_cell_angle_beta                 104.748(6)
_cell_angle_gamma                90
_cell_volume                     2801(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    38166
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.362
_cell_measurement_theta_min      3.150
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.937
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0743
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            38166
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.362
_diffrn_reflns_theta_min         3.150
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2491
_reflns_number_total             2851
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.819
_refine_diff_density_min         -1.259
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.229
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2851
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0879
_refine_ls_restrained_S_all      1.221
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0232P)²+35.7444P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2050
_refine_ls_wR_factor_ref         0.2112
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid body (RIGU) restrains
 C1, N4, C3, N3, C2, N1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Ternary CH refined with riding coordinates:
 C6(H6)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
3.c Aromatic/amide H refined with riding coordinates:
 N5(H5), N2(H2), C10(H10)
3.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
3.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.15919(5) 0.5870(2) 0.17420(5) 0.0250(3) Uani 1 1 d . . . . .
N4 N 0.09925(18) 0.6009(6) 0.25915(16) 0.0195(7) Uani 1 1 d . U . . .
N1 N 0.22925(17) 0.5904(6) 0.28031(15) 0.0190(7) Uani 1 1 d . U . . .
N5 N 0.04394(19) 0.6233(7) 0.33285(17) 0.0252(9) Uani 1 1 d . . . . .
H5 H 0.0026 0.6206 0.3061 0.030 Uiso 1 1 calc R U . . .
N3 N 0.17001(18) 0.6084(7) 0.35711(16) 0.0219(8) Uani 1 1 d . U . . .
N2 N 0.29583(18) 0.5890(7) 0.37341(16) 0.0245(8) Uani 1 1 d . . . . .
H2 H 0.3341 0.5760 0.3593 0.029 Uiso 1 1 calc R U . . .
C2 C 0.2303(2) 0.5963(8) 0.33696(19) 0.0201(9) Uani 1 1 d . U . . .
C1 C 0.1628(2) 0.5954(7) 0.24649(18) 0.0176(8) Uani 1 1 d . U . . .
C3 C 0.1068(2) 0.6096(7) 0.31683(19) 0.0198(9) Uani 1 1 d . U . . .
C4 C 0.0401(2) 0.6422(9) 0.3918(2) 0.0311(12) Uani 1 1 d . . . . .
H4A H -0.0047 0.7216 0.3930 0.037 Uiso 1 1 calc R U . . .
H4B H 0.0827 0.7244 0.4135 0.037 Uiso 1 1 calc R U . . .
C6 C 0.3090(3) 0.6009(10) 0.4350(2) 0.0315(11) Uani 1 1 d . . . . .
H6 H 0.2680 0.5273 0.4464 0.038 Uiso 1 1 calc R U . . .
C5 C 0.0391(4) 0.4293(12) 0.4196(3) 0.0517(17) Uani 1 1 d . . . . .
H5A H -0.0025 0.3462 0.3979 0.078 Uiso 1 1 calc R U . . .
H5B H 0.0344 0.4494 0.4585 0.078 Uiso 1 1 calc R U . . .
H5C H 0.0846 0.3535 0.4206 0.078 Uiso 1 1 calc R U . . .
C7 C 0.3117(3) 0.8306(11) 0.4551(3) 0.0466(15) Uani 1 1 d . . . . .
H7A H 0.3533 0.9029 0.4461 0.070 Uiso 1 1 calc R U . . .
H7B H 0.3174 0.8338 0.4963 0.070 Uiso 1 1 calc R U . . .
H7C H 0.2663 0.9028 0.4358 0.070 Uiso 1 1 calc R U . . .
C8 C 0.3802(3) 0.4840(12) 0.4622(3) 0.0503(16) Uani 1 1 d . . . . .
H8A H 0.3762 0.3357 0.4496 0.076 Uiso 1 1 calc R U . . .
H8B H 0.3893 0.4891 0.5037 0.076 Uiso 1 1 calc R U . . .
H8C H 0.4208 0.5524 0.4508 0.076 Uiso 1 1 calc R U . . .
O2 O 0.41697(16) 0.5873(6) 0.31769(14) 0.0281(8) Uani 1 1 d . . . . .
O1 O 0.34043(15) 0.5989(6) 0.23010(14) 0.0255(7) Uani 1 1 d . . . . .
H1 H 0.3082 0.6005 0.2483 0.038 Uiso 1 1 calc R U . . .
C10 C 0.4653(2) 0.5969(8) 0.2357(2) 0.0228(9) Uani 1 1 d . . . . .
H10 H 0.4530 0.5978 0.1953 0.027 Uiso 1 1 calc R U . . .
C9 C 0.4059(2) 0.5955(7) 0.2661(2) 0.0209(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.742(4) . ?
N4 C1 1.315(5) . ?
N4 C3 1.374(6) . ?
N1 C2 1.373(6) . ?
N1 C1 1.316(5) . ?
N5 H5 0.8800 . ?
N5 C3 1.345(5) . ?
N5 C4 1.458(6) . ?
N3 C2 1.353(5) . ?
N3 C3 1.340(5) . ?
N2 H2 0.8800 . ?
N2 C2 1.329(5) . ?
N2 C6 1.457(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.504(9) . ?
C6 H6 1.0000 . ?
C6 C7 1.523(9) . ?
C6 C8 1.530(7) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
O2 C9 1.218(6) . ?
O1 H1 0.8400 . ?
O1 C9 1.323(5) . ?
C10 C10 1.320(9) 2_655 ?
C10 H10 0.9500 . ?
C10 C9 1.495(6) . ?

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 N4 C3 112.1(4) . . ?
C1 N1 C2 113.1(3) . . ?
C3 N5 H5 118.0 . . ?
C3 N5 C4 124.0(4) . . ?
C4 N5 H5 118.0 . . ?
C3 N3 C2 114.5(4) . . ?
C2 N2 H2 117.6 . . ?
C2 N2 C6 124.8(4) . . ?
C6 N2 H2 117.6 . . ?
N3 C2 N1 124.5(4) . . ?
N2 C2 N1 116.1(4) . . ?
N2 C2 N3 119.4(4) . . ?
N4 C1 Cl1 115.7(3) . . ?
N4 C1 N1 129.8(4) . . ?
N1 C1 Cl1 114.5(3) . . ?
N5 C3 N4 115.4(4) . . ?
N3 C3 N4 126.0(4) . . ?
N3 C3 N5 118.7(4) . . ?
N5 C4 H4A 109.2 . . ?
N5 C4 H4B 109.2 . . ?
N5 C4 C5 112.3(5) . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
N2 C6 H6 108.5 . . ?
N2 C6 C7 111.2(5) . . ?
N2 C6 C8 108.7(4) . . ?
C7 C6 H6 108.5 . . ?
C7 C6 C8 111.4(5) . . ?
C8 C6 H6 108.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C9 O1 H1 109.5 . . ?
C10 C10 H10 119.7 2_655 . ?
C10 C10 C9 120.7(6) 2_655 . ?
C9 C10 H10 119.7 . . ?
O2 C9 O1 124.7(4) . . ?
O2 C9 C10 123.8(4) . . ?
O1 C9 C10 111.5(4) . . ?

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
C2 N1 C1 Cl1 -179.7(3) . . . . ?
C2 N1 C1 N4 -1.5(7) . . . . ?
C2 N3 C3 N4 -0.4(7) . . . . ?
C2 N3 C3 N5 -179.4(4) . . . . ?
C2 N2 C6 C7 -84.3(6) . . . . ?
C2 N2 C6 C8 152.7(5) . . . . ?
C1 N4 C3 N5 177.7(4) . . . . ?
C1 N4 C3 N3 -1.3(7) . . . . ?
C1 N1 C2 N3 -0.7(7) . . . . ?
C1 N1 C2 N2 179.2(4) . . . . ?
C3 N4 C1 Cl1 -179.4(3) . . . . ?
C3 N4 C1 N1 2.4(7) . . . . ?
C3 N5 C4 C5 -88.1(6) . . . . ?
C3 N3 C2 N1 1.5(7) . . . . ?
C3 N3 C2 N2 -178.4(4) . . . . ?
C4 N5 C3 N4 -177.6(4) . . . . ?
C4 N5 C3 N3 1.5(7) . . . . ?
C6 N2 C2 N1 177.7(5) . . . . ?
C6 N2 C2 N3 -2.4(8) . . . . ?
C10 C10 C9 O2 -2.5(6) 2_655 . . . ?
C10 C10 C9 O1 179.1(3) 2_655 . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
