# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 2311920'
loop_
_audit_author_name
_audit_author_address
'Eliska Zmeskalova'
;Institute of Physics of the Czech Academy of Sciences
Czech Republic
;
_audit_update_record             
;
2023-12-04 deposited with the CCDC.	2024-09-26 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_refine_special_details          
; 
 ? 
;

#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   7.62900(10)
_cell_length_b                   7.67020(10)
_cell_length_c                   14.1025(4)
_cell_angle_alpha                94.2128(19)
_cell_angle_beta                 99.531(2)
_cell_angle_gamma                98.0165(16)
_cell_volume                     801.93(3)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.2955 0.4335 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C13 H18 Cl1 N2 O2 P1 S2 
# Dc =      1.51 Fooo =    380.00 Mu =     55.35 M =    364.86
# Found Formula = C12 H18 Cl1 N2 O2 P1 S2 
# Dc =      1.46 FOOO =    368.00 Mu =     55.13 M =    352.85

_chemical_formula_sum            'C12 H18 Cl1 N2 O2 P1 S2'
_chemical_formula_moiety         'C12 H18 Cl1 N2 O2 P1 S2'
_chemical_compound_source        .
_chemical_formula_weight         352.85


_cell_measurement_reflns_used    9497
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      73.95
_cell_measurement_temperature    95

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.142
_exptl_crystal_size_mid          0.273
_exptl_crystal_size_max          0.491

_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    5.513

# Sheldrick geometric approximatio 0.22 0.46 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.11
_exptl_absorpt_correction_T_max  0.46
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      95
_diffrn_reflns_number            11539
_diffrn_reflns_av_unetI/netI     0.026
_reflns_number_total             3210
_diffrn_reflns_av_R_equivalents  0.023
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 3210 
# Theoretical number of reflections is about 6523 


_diffrn_reflns_theta_min         3.193
_diffrn_reflns_theta_max         74.111
_diffrn_measured_fraction_theta_max 0.981

_diffrn_reflns_theta_full        68.291
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              -9
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_oxford_diffrn_Wilson_B_factor   1.02
_oxford_diffrn_Wilson_scale      0.01

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.28
_refine_diff_density_max         0.54


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3209
_oxford_refine_ls_R_factor_ref   0.0258
_refine_ls_R_factor_all          0.0258
_refine_ls_wR_factor_ref         0.0713
_refine_ls_wR_factor_all         0.0713
_refine_ls_goodness_of_fit_ref   0.9743
_refine_ls_shift/su_max          0.0012674
_refine_ls_shift/su_mean         0.0000347


# Computed with I/sigma = -10 
_oxford_reflns_number_all        3209
_oxford_refine_ls_R_factor_all   0.0258
_oxford_refine_ls_wR_factor_all  0.0713

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3153
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_gt          0.0710


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.56P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Cl1 Cl 0.24735(5) 1.28829(4) 0.50474(3) 0.0198 1.0000 Uani . . . . . .
C2 C 0.27963(19) 1.08760(18) 0.44798(11) 0.0145 1.0000 Uani . . . . . .
C3 C 0.38225(19) 1.08873(19) 0.37592(12) 0.0177 1.0000 Uani . . . . . .
C4 C 0.40857(19) 0.92795(19) 0.33245(11) 0.0162 1.0000 Uani . . . . . .
C5 C 0.33268(18) 0.76853(18) 0.35998(10) 0.0119 1.0000 Uani . . . . . .
C6 C 0.36359(18) 0.59393(18) 0.31329(10) 0.0130 1.0000 Uani . . . . . .
N7 N 0.19678(15) 0.48619(15) 0.26148(9) 0.0124 1.0000 Uani . . . . . .
C8 C 0.12520(18) 0.50070(17) 0.17000(10) 0.0108 1.0000 Uani . . . . . .
S9 S 0.22448(4) 0.63808(4) 0.10002(2) 0.0143 1.0000 Uani . . . . . .
N10 N -0.03680(15) 0.39582(15) 0.13270(8) 0.0111 1.0000 Uani . . . . . .
P11 P -0.15977(4) 0.24630(4) 0.18524(3) 0.0109 1.0000 Uani . . . . . .
S12 S -0.19780(5) 0.32730(5) 0.31205(3) 0.0178 1.0000 Uani . . . . . .
O13 O -0.05519(13) 0.08482(13) 0.18017(8) 0.0157 1.0000 Uani . . . . . .
C14 C -0.0873(2) -0.06887(19) 0.23427(12) 0.0202 1.0000 Uani . . . . . .
C15 C -0.2228(2) -0.21282(19) 0.17489(12) 0.0202 1.0000 Uani . . . . . .
O16 O -0.33218(13) 0.18872(13) 0.10587(8) 0.0143 1.0000 Uani . . . . . .
C17 C -0.48913(19) 0.28153(19) 0.09581(12) 0.0166 1.0000 Uani . . . . . .
C18 C -0.65510(19) 0.1472(2) 0.08646(12) 0.0198 1.0000 Uani . . . . . .
C19 C 0.2296(2) 0.77170(19) 0.43268(11) 0.0155 1.0000 Uani . . . . . .
C20 C 0.2030(2) 0.9304(2) 0.47748(11) 0.0171 1.0000 Uani . . . . . .
H31 H 0.4391 1.1942 0.3607 0.0213 1.0000 Uiso R . . . . .
H41 H 0.4808 0.9326 0.2864 0.0214 1.0000 Uiso R . . . . .
H61 H 0.4138 0.5252 0.3656 0.0165 1.0000 Uiso R . . . . .
H62 H 0.4509 0.6091 0.2694 0.0161 1.0000 Uiso R . . . . .
H141 H -0.1202 -0.0340 0.2981 0.0251 1.0000 Uiso R . . . . .
H142 H 0.0236 -0.1123 0.2428 0.0256 1.0000 Uiso R . . . . .
H151 H -0.2319 -0.3109 0.2115 0.0303 1.0000 Uiso R . . . . .
H153 H -0.3385 -0.1737 0.1621 0.0320 1.0000 Uiso R . . . . .
H152 H -0.1830 -0.2459 0.1200 0.0342 1.0000 Uiso R . . . . .
H171 H -0.4794 0.3676 0.1486 0.0211 1.0000 Uiso R . . . . .
H172 H -0.4923 0.3470 0.0382 0.0235 1.0000 Uiso R . . . . .
H181 H -0.7590 0.2055 0.0760 0.0320 1.0000 Uiso R . . . . .
H182 H -0.6653 0.0888 0.1416 0.0338 1.0000 Uiso R . . . . .
H183 H -0.6568 0.0509 0.0414 0.0310 1.0000 Uiso R . . . . .
H191 H 0.1793 0.6646 0.4502 0.0178 1.0000 Uiso R . . . . .
H201 H 0.1308 0.9384 0.5271 0.0227 1.0000 Uiso R . . . . .
H101 H -0.0761 0.3988 0.0713 0.0155 1.0000 Uiso R . . . . .
H71 H 0.1303 0.4228 0.2936 0.0149 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       19.4(18)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          9.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 . C2 . 1.7495(14) yes
C2 . C3 . 1.382(2) yes
C2 . C20 . 1.388(2) yes
C3 . C4 . 1.391(2) yes
C3 . H31 . 0.920 no
C4 . C5 . 1.389(2) yes
C4 . H41 . 0.919 no
C5 . C6 . 1.5141(19) yes
C5 . C19 . 1.393(2) yes
C6 . N7 . 1.4650(17) yes
C6 . H61 . 0.994 no
C6 . H62 . 0.983 no
N7 . C8 . 1.3341(18) yes
N7 . H71 . 0.860 no
C8 . S9 . 1.6839(14) yes
C8 . N10 . 1.3772(18) yes
N10 . P11 . 1.6731(12) yes
N10 . H101 . 0.871 no
P11 . S12 . 1.9306(5) yes
P11 . O13 . 1.5676(10) yes
P11 . O16 . 1.5671(10) yes
O13 . C14 . 1.4647(17) yes
C14 . C15 . 1.499(2) yes
C14 . H141 . 1.002 no
C14 . H142 . 0.945 no
C15 . H151 . 0.944 no
C15 . H153 . 0.965 no
C15 . H152 . 0.908 no
O16 . C17 . 1.4686(16) yes
C17 . C18 . 1.498(2) yes
C17 . H171 . 0.944 no
C17 . H172 . 0.985 no
C18 . H181 . 0.959 no
C18 . H182 . 0.935 no
C18 . H183 . 0.936 no
C19 . C20 . 1.386(2) yes
C19 . H191 . 0.925 no
C20 . H201 . 0.963 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Cl1 . C2 . C3 . 119.53(11) yes
Cl1 . C2 . C20 . 118.98(12) yes
C3 . C2 . C20 . 121.48(13) yes
C2 . C3 . C4 . 118.78(13) yes
C2 . C3 . H31 . 120.1 no
C4 . C3 . H31 . 120.9 no
C3 . C4 . C5 . 121.07(14) yes
C3 . C4 . H41 . 117.0 no
C5 . C4 . H41 . 122.0 no
C4 . C5 . C6 . 120.86(13) yes
C4 . C5 . C19 . 118.81(13) yes
C6 . C5 . C19 . 120.32(12) yes
C5 . C6 . N7 . 112.67(11) yes
C5 . C6 . H61 . 107.8 no
N7 . C6 . H61 . 106.8 no
C5 . C6 . H62 . 112.5 no
N7 . C6 . H62 . 109.3 no
H61 . C6 . H62 . 107.5 no
C6 . N7 . C8 . 123.97(12) yes
C6 . N7 . H71 . 118.8 no
C8 . N7 . H71 . 116.3 no
N7 . C8 . S9 . 123.07(10) yes
N7 . C8 . N10 . 117.15(12) yes
S9 . C8 . N10 . 119.78(11) yes
C8 . N10 . P11 . 129.28(10) yes
C8 . N10 . H101 . 115.9 no
P11 . N10 . H101 . 114.5 no
N10 . P11 . S12 . 114.70(4) yes
N10 . P11 . O13 . 101.81(6) yes
S12 . P11 . O13 . 115.90(5) yes
N10 . P11 . O16 . 102.34(6) yes
S12 . P11 . O16 . 116.58(4) yes
O13 . P11 . O16 . 103.48(6) yes
P11 . O13 . C14 . 123.23(9) yes
O13 . C14 . C15 . 111.20(12) yes
O13 . C14 . H141 . 111.3 no
C15 . C14 . H141 . 112.8 no
O13 . C14 . H142 . 103.9 no
C15 . C14 . H142 . 106.3 no
H141 . C14 . H142 . 110.9 no
C14 . C15 . H151 . 107.5 no
C14 . C15 . H153 . 109.8 no
H151 . C15 . H153 . 108.9 no
C14 . C15 . H152 . 109.5 no
H151 . C15 . H152 . 108.2 no
H153 . C15 . H152 . 112.7 no
P11 . O16 . C17 . 123.71(9) yes
O16 . C17 . C18 . 108.43(11) yes
O16 . C17 . H171 . 111.0 no
C18 . C17 . H171 . 111.8 no
O16 . C17 . H172 . 109.1 no
C18 . C17 . H172 . 110.7 no
H171 . C17 . H172 . 105.8 no
C17 . C18 . H181 . 109.2 no
C17 . C18 . H182 . 114.6 no
H181 . C18 . H182 . 104.8 no
C17 . C18 . H183 . 112.7 no
H181 . C18 . H183 . 114.9 no
H182 . C18 . H183 . 100.3 no
C5 . C19 . C20 . 121.03(13) yes
C5 . C19 . H191 . 118.0 no
C20 . C19 . H191 . 121.0 no
C2 . C20 . C19 . 118.83(14) yes
C2 . C20 . H201 . 117.5 no
C19 . C20 . H201 . 123.6 no



# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
-1 2 16 x .
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
####################################################################### 
# 
# 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_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2311922'
loop_
_audit_author_name
_audit_author_address
'Eliska Zmeskalova'
;Institute of Physics of the Czech Academy of Sciences
Czech Republic
;
_audit_update_record             
;
2023-12-04 deposited with the CCDC.	2024-09-26 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_refine_special_details          
; 
 ? 
;

#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   7.8502(2)
_cell_length_b                   10.1868(4)
_cell_length_c                   11.6914(4)
_cell_angle_alpha                113.275(3)
_cell_angle_beta                 97.462(3)
_cell_angle_gamma                97.123(3)
_cell_volume                     835.66(5)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.2955 0.4335 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Ni -3.0029 0.5091 12.8376 3.8785 7.2920 0.2565 4.4438 12.1763 2.3800 66.3421
1.0341 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C12 H18 Cl3 N2 Ni1 O1 P1 S2 
# Dc =      1.85 Fooo =    476.00 Mu =     93.44 M =    466.46
# Found Formula = C12 H17 Cl1 N2 Ni0.50 O2 P1 S2 
# Dc =      1.51 FOOO =    394.00 Mu =     58.60 M =    381.19

_chemical_formula_sum            'C12 H17 Cl1 N2 Ni0.50 O2 P1 S2'
_chemical_formula_moiety         'C12 H17 Cl1 N2 Ni0.50 O2 P1 S2'
_chemical_compound_source        .
_chemical_formula_weight         381.19


_cell_measurement_reflns_used    7760
_cell_measurement_theta_min      4.18
_cell_measurement_theta_max      67.38
_cell_measurement_temperature    120

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_size_min          0.123
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_max          0.312

_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             394
_exptl_absorpt_coefficient_mu    5.860

# Sheldrick geometric approximatio 0.21 0.49 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.15
_exptl_absorpt_correction_T_max  0.49
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      120
_diffrn_reflns_number            12744
_diffrn_reflns_av_unetI/netI     0.078
_reflns_number_total             2996
_diffrn_reflns_av_R_equivalents  0.096
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2996 
# Theoretical number of reflections is about 6035 


_diffrn_reflns_theta_min         4.198
_diffrn_reflns_theta_max         67.581
_diffrn_measured_fraction_theta_max 0.991

_diffrn_reflns_theta_full        66.285
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              -12
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   2.08
_oxford_diffrn_Wilson_scale      0.02

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.81
_refine_diff_density_max         0.76


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2996
_oxford_refine_ls_R_factor_ref   0.0534
_refine_ls_R_factor_all          0.0534
_refine_ls_wR_factor_ref         0.1414
_refine_ls_wR_factor_all         0.1414
_refine_ls_goodness_of_fit_ref   1.0003
_refine_ls_shift/su_max          0.0002613
_refine_ls_shift/su_mean         0.0000195


# Computed with I/sigma = -10 
_oxford_reflns_number_all        2996
_oxford_refine_ls_R_factor_all   0.0534
_oxford_refine_ls_wR_factor_all  0.1414

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2716
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_gt          0.1338


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.09P)² + 0.82P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Ni1 Ni 0.0000 1.0000 0.5000 0.0186 1.0000 Uani S . . . . .
S2 S 0.16902(10) 0.83405(8) 0.47302(7) 0.0234 1.0000 Uani . . . . . .
C3 C 0.2431(4) 0.9231(3) 0.3850(3) 0.0201 1.0000 Uani . . . . . .
N4 N 0.1493(3) 1.0267(3) 0.3917(2) 0.0214 1.0000 Uani . . . . . .
P5 P 0.17478(10) 1.15490(8) 0.33955(7) 0.0219 1.0000 Uani . . . . . .
S6 S 0.33370(16) 1.13540(10) 0.22309(10) 0.0492 1.0000 Uani . . . . . .
O7 O -0.0145(3) 1.1689(2) 0.2892(2) 0.0277 1.0000 Uani . . . . . .
C8 C -0.1193(7) 1.0581(4) 0.1699(4) 0.0553 1.0000 Uani . . . . . .
C9 C -0.2434(7) 1.1197(7) 0.1170(5) 0.0829 1.0000 Uani . . . . . .
O10 O 0.2269(3) 1.2965(2) 0.46751(19) 0.0227 1.0000 Uani . . . . . .
C11 C 0.2399(5) 1.4405(3) 0.4687(3) 0.0289 1.0000 Uani . . . . . .
C12 C 0.2725(5) 1.5481(4) 0.6048(3) 0.0382 1.0000 Uani . . . . . .
N13 N 0.3717(3) 0.8928(3) 0.3228(2) 0.0249 1.0000 Uani . . . . . .
C14 C 0.4690(5) 0.7789(4) 0.3208(3) 0.0303 1.0000 Uani . . . . . .
C15 C 0.5633(4) 0.7347(3) 0.2107(3) 0.0214 1.0000 Uani . . . . . .
C16 C 0.4846(4) 0.7165(3) 0.0903(3) 0.0254 1.0000 Uani . . . . . .
C17 C 0.5731(4) 0.6722(4) -0.0102(3) 0.0278 1.0000 Uani . . . . . .
C18 C 0.7389(5) 0.6451(4) 0.0110(3) 0.0292 1.0000 Uani . . . . . .
Cl19 Cl 0.84798(16) 0.58485(14) -0.11521(10) 0.0580 1.0000 Uani . . . . . .
C20 C 0.8212(4) 0.6634(4) 0.1300(3) 0.0298 1.0000 Uani . . . . . .
C21 C 0.7323(4) 0.7084(3) 0.2295(3) 0.0242 1.0000 Uani . . . . . .
H81 H -0.0466 1.0147 0.1111 0.0655 1.0000 Uiso R . . . . .
H82 H -0.1829 0.9828 0.1859 0.0652 1.0000 Uiso R . . . . .
H91 H -0.3163 1.0478 0.0395 0.1257 1.0000 Uiso R . . . . .
H92 H -0.1780 1.1935 0.1000 0.1267 1.0000 Uiso R . . . . .
H93 H -0.3137 1.1640 0.1757 0.1262 1.0000 Uiso R . . . . .
H111 H 0.3380 1.4555 0.4292 0.0348 1.0000 Uiso R . . . . .
H112 H 0.1312 1.4442 0.4213 0.0347 1.0000 Uiso R . . . . .
H121 H 0.2863 1.6458 0.6089 0.0559 1.0000 Uiso R . . . . .
H122 H 0.3776 1.5403 0.6514 0.0558 1.0000 Uiso R . . . . .
H123 H 0.1746 1.5281 0.6426 0.0561 1.0000 Uiso R . . . . .
H142 H 0.5538 0.8140 0.3995 0.0359 1.0000 Uiso R . . . . .
H141 H 0.3853 0.6954 0.3138 0.0356 1.0000 Uiso R . . . . .
H161 H 0.3703 0.7347 0.0759 0.0303 1.0000 Uiso R . . . . .
H171 H 0.5213 0.6601 -0.0924 0.0335 1.0000 Uiso R . . . . .
H201 H 0.9351 0.6465 0.1442 0.0363 1.0000 Uiso R . . . . .
H211 H 0.7876 0.7203 0.3106 0.0286 1.0000 Uiso R . . . . .
H131 H 0.4047 0.9473 0.2843 0.0293 1.0000 Uiso R . . . . .

_refine_ls_extinction_coef       18(3)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          8.7(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ni1 . C3 2_576 2.503(3) yes
Ni1 . N4 2_576 1.906(2) yes
Ni1 . S2 2_576 2.2274(7) yes
Ni1 . P5 2_576 3.2190(7) yes
Ni1 . S2 . 2.2274(7) yes
Ni1 . C3 . 2.503(3) yes
Ni1 . N4 . 1.906(2) yes
Ni1 . P5 . 3.2190(7) yes
S2 . C3 . 1.727(3) yes
C3 . N4 . 1.343(4) yes
C3 . N13 . 1.317(4) yes
N4 . P5 . 1.647(2) yes
P5 . S6 . 1.9336(11) yes
P5 . O7 . 1.571(2) yes
P5 . O10 . 1.573(2) yes
O7 . C8 . 1.457(4) yes
C8 . C9 . 1.423(7) yes
C8 . H81 . 0.958 no
C8 . H82 . 0.957 no
C9 . H91 . 0.960 no
C9 . H92 . 0.958 no
C9 . H93 . 0.946 no
O10 . C11 . 1.452(4) yes
C11 . C12 . 1.498(5) yes
C11 . H111 . 0.974 no
C11 . H112 . 0.968 no
C12 . H121 . 0.969 no
C12 . H122 . 0.958 no
C12 . H123 . 0.974 no
N13 . C14 . 1.460(4) yes
N13 . H131 . 0.877 no
C14 . C15 . 1.510(4) yes
C14 . H142 . 0.969 no
C14 . H141 . 0.977 no
C15 . C16 . 1.391(4) yes
C15 . C21 . 1.392(4) yes
C16 . C17 . 1.392(4) yes
C16 . H161 . 0.946 no
C17 . C18 . 1.375(5) yes
C17 . H171 . 0.947 no
C18 . Cl19 . 1.741(3) yes
C18 . C20 . 1.386(5) yes
C20 . C21 . 1.385(5) yes
C20 . H201 . 0.937 no
C21 . H211 . 0.944 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 2_576 Ni1 . N4 2_576 31.96(10) yes
C3 2_576 Ni1 . S2 2_576 42.32(7) yes
N4 2_576 Ni1 . S2 2_576 74.27(7) yes
C3 2_576 Ni1 . P5 2_576 54.97(7) yes
N4 2_576 Ni1 . P5 2_576 23.15(7) yes
S2 2_576 Ni1 . P5 2_576 97.25(2) yes
C3 2_576 Ni1 . S2 . 137.68(7) yes
N4 2_576 Ni1 . S2 . 105.73(7) yes
S2 2_576 Ni1 . S2 . 179.99 yes
P5 2_576 Ni1 . S2 . 82.75(2) yes
C3 2_576 Ni1 . C3 . 180.00 yes
N4 2_576 Ni1 . C3 . 148.04(10) yes
S2 2_576 Ni1 . C3 . 137.68(7) yes
P5 2_576 Ni1 . C3 . 125.03(7) yes
S2 . Ni1 . C3 . 42.32(7) yes
C3 2_576 Ni1 . N4 . 148.04(10) yes
N4 2_576 Ni1 . N4 . 179.99 yes
S2 2_576 Ni1 . N4 . 105.73(7) yes
P5 2_576 Ni1 . N4 . 156.85(7) yes
S2 . Ni1 . N4 . 74.27(7) yes
C3 2_576 Ni1 . P5 . 125.03(7) yes
N4 2_576 Ni1 . P5 . 156.85(7) yes
S2 2_576 Ni1 . P5 . 82.75(2) yes
P5 2_576 Ni1 . P5 . 180.00 yes
S2 . Ni1 . P5 . 97.25(2) yes
C3 . Ni1 . N4 . 31.96(10) yes
C3 . Ni1 . P5 . 54.97(7) yes
N4 . Ni1 . P5 . 23.15(7) yes
Ni1 . S2 . C3 . 77.41(10) yes
Ni1 . C3 . S2 . 60.27(9) yes
Ni1 . C3 . N4 . 48.68(14) yes
S2 . C3 . N4 . 108.9(2) yes
Ni1 . C3 . N13 . 175.1(2) yes
S2 . C3 . N13 . 124.5(2) yes
N4 . C3 . N13 . 126.5(3) yes
C3 . N4 . Ni1 . 99.36(18) yes
C3 . N4 . P5 . 130.3(2) yes
Ni1 . N4 . P5 . 129.79(14) yes
N4 . P5 . Ni1 . 27.06(9) yes
N4 . P5 . S6 . 116.30(10) yes
Ni1 . P5 . S6 . 143.30(4) yes
N4 . P5 . O7 . 106.19(13) yes
Ni1 . P5 . O7 . 87.43(9) yes
S6 . P5 . O7 . 114.85(10) yes
N4 . P5 . O10 . 101.61(12) yes
Ni1 . P5 . O10 . 86.33(8) yes
S6 . P5 . O10 . 115.35(10) yes
O7 . P5 . O10 . 100.56(11) yes
P5 . O7 . C8 . 120.8(3) yes
O7 . C8 . C9 . 110.1(3) yes
O7 . C8 . H81 . 111.1 no
C9 . C8 . H81 . 110.8 no
O7 . C8 . H82 . 109.2 no
C9 . C8 . H82 . 107.7 no
H81 . C8 . H82 . 107.9 no
C8 . C9 . H91 . 111.5 no
C8 . C9 . H92 . 106.8 no
H91 . C9 . H92 . 109.5 no
C8 . C9 . H93 . 110.8 no
H91 . C9 . H93 . 109.9 no
H92 . C9 . H93 . 108.4 no
P5 . O10 . C11 . 121.39(18) yes
O10 . C11 . C12 . 107.2(3) yes
O10 . C11 . H111 . 107.5 no
C12 . C11 . H111 . 110.8 no
O10 . C11 . H112 . 108.4 no
C12 . C11 . H112 . 111.5 no
H111 . C11 . H112 . 111.1 no
C11 . C12 . H121 . 109.2 no
C11 . C12 . H122 . 110.7 no
H121 . C12 . H122 . 108.2 no
C11 . C12 . H123 . 109.0 no
H121 . C12 . H123 . 111.0 no
H122 . C12 . H123 . 108.7 no
C3 . N13 . C14 . 123.4(3) yes
C3 . N13 . H131 . 118.2 no
C14 . N13 . H131 . 118.3 no
N13 . C14 . C15 . 111.4(3) yes
N13 . C14 . H142 . 109.4 no
C15 . C14 . H142 . 109.2 no
N13 . C14 . H141 . 107.7 no
C15 . C14 . H141 . 110.1 no
H142 . C14 . H141 . 109.2 no
C14 . C15 . C16 . 121.8(3) yes
C14 . C15 . C21 . 119.1(3) yes
C16 . C15 . C21 . 119.1(3) yes
C15 . C16 . C17 . 120.6(3) yes
C15 . C16 . H161 . 120.3 no
C17 . C16 . H161 . 119.1 no
C16 . C17 . C18 . 119.0(3) yes
C16 . C17 . H171 . 121.4 no
C18 . C17 . H171 . 119.6 no
C17 . C18 . Cl19 . 119.2(3) yes
C17 . C18 . C20 . 121.8(3) yes
Cl19 . C18 . C20 . 119.0(2) yes
C18 . C20 . C21 . 118.7(3) yes
C18 . C20 . H201 . 121.3 no
C21 . C20 . H201 . 119.9 no
C15 . C21 . C20 . 120.8(3) yes
C15 . C21 . H211 . 120.2 no
C20 . C21 . H211 . 119.0 no


# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
####################################################################### 
# 
# 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_I_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2311923'
loop_
_audit_author_name
_audit_author_address
'Eliska Zmeskalova'
;Institute of Physics of the Czech Academy of Sciences
Czech Republic
;
_audit_update_record             
;
2023-12-04 deposited with the CCDC.	2024-09-26 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_refine_special_details          
; 
 ? 
;

#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   8.2171(3)
_cell_length_b                   9.9942(4)
_cell_length_c                   11.1612(4)
_cell_angle_alpha                113.611(3)
_cell_angle_beta                 93.655(3)
_cell_angle_gamma                92.926(3)
_cell_volume                     835.21(6)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.2955 0.4335 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Ni -3.0029 0.5091 12.8376 3.8785 7.2920 0.2565 4.4438 12.1763 2.3800 66.3421
1.0341 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C1 H1 Cl1 N1 Ni1 O1 P1 S1 
# Dc =      0.80 Fooo =    196.00 Mu =     48.89 M =    200.23
# Found Formula = C13 H20 N2 Ni0.50 O2 P1 S2 
# Dc =      1.43 FOOO =    378.00 Mu =     43.91 M =    360.77

_chemical_formula_sum            'C13 H20 N2 Ni0.50 O2 P1 S2'
_chemical_formula_moiety         'C13 H20 N2 Ni0.50 O2 P1 S2'
_chemical_compound_source        .
_chemical_formula_weight         360.77


_cell_measurement_reflns_used    7860
_cell_measurement_theta_min      4.31
_cell_measurement_theta_max      67.71
_cell_measurement_temperature    120

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_min          0.221
_exptl_crystal_size_mid          0.278
_exptl_crystal_size_max          0.762

_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             378
_exptl_absorpt_coefficient_mu    4.391

# Sheldrick geometric approximatio 0.30 0.38 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.03
_exptl_absorpt_correction_T_max  0.38
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      120
_diffrn_reflns_number            13759
_diffrn_reflns_av_unetI/netI     0.069
_reflns_number_total             2986
_diffrn_reflns_av_R_equivalents  0.068
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2986 
# Theoretical number of reflections is about 6037 


_diffrn_reflns_theta_min         4.342
_diffrn_reflns_theta_max         67.614
_diffrn_measured_fraction_theta_max 0.993

_diffrn_reflns_theta_full        66.262
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              -11
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              13

_oxford_diffrn_Wilson_B_factor   1.65
_oxford_diffrn_Wilson_scale      0.02

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.91
_refine_diff_density_max         0.64


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2985
_oxford_refine_ls_R_factor_ref   0.0490
_refine_ls_R_factor_all          0.0490
_refine_ls_wR_factor_ref         0.1393
_refine_ls_wR_factor_all         0.1393
_refine_ls_goodness_of_fit_ref   0.9943
_refine_ls_shift/su_max          0.0001551
_refine_ls_shift/su_mean         0.0000200


# Computed with I/sigma = -10 
_oxford_reflns_number_all        2985
_oxford_refine_ls_R_factor_all   0.0490
_oxford_refine_ls_wR_factor_all  0.1393

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2692
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_gt          0.1332


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.10P)² + 0.40P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Ni1 Ni 0.5000 0.0000 0.5000 0.0189 1.0000 Uani S . . . . .
S2 S 0.30203(8) 0.06219(7) 0.39143(6) 0.0227 1.0000 Uani . . . . . .
C3 C 0.2526(3) 0.1416(3) 0.5519(3) 0.0212 1.0000 Uani . . . . . .
N4 N 0.3652(3) 0.1141(2) 0.6304(2) 0.0215 1.0000 Uani . . . . . .
P5 P 0.36491(8) 0.15009(7) 0.78782(6) 0.0201 1.0000 Uani . . . . . .
O6 O 0.5499(2) 0.17070(19) 0.84226(17) 0.0197 1.0000 Uani . . . . . .
C7 C 0.6510(3) 0.3002(3) 0.8509(3) 0.0243 1.0000 Uani . . . . . .
C8 C 0.8063(4) 0.3097(3) 0.9318(3) 0.0364 1.0000 Uani . . . . . .
O9 O 0.3123(3) -0.0042(2) 0.78678(19) 0.0313 1.0000 Uani . . . . . .
C10 C 0.2590(4) -0.0231(3) 0.9010(3) 0.0327 1.0000 Uani . . . . . .
C11 C 0.1001(4) -0.1151(4) 0.8601(3) 0.0366 1.0000 Uani . . . . . .
S12 S 0.23781(9) 0.30820(8) 0.88895(7) 0.0322 1.0000 Uani . . . . . .
N13 N 0.1225(3) 0.2143(3) 0.5879(2) 0.0266 1.0000 Uani . . . . . .
C14 C 0.0082(4) 0.2408(3) 0.4950(3) 0.0320 1.0000 Uani . . . . . .
C15 C -0.1153(4) 0.3447(3) 0.5654(3) 0.0229 1.0000 Uani . . . . . .
C16 C -0.0699(4) 0.4722(3) 0.6783(3) 0.0264 1.0000 Uani . . . . . .
C17 C -0.1862(4) 0.5649(3) 0.7400(3) 0.0258 1.0000 Uani . . . . . .
C18 C -0.3503(4) 0.5361(3) 0.6914(3) 0.0228 1.0000 Uani . . . . . .
C19 C -0.3943(4) 0.4095(3) 0.5785(3) 0.0228 1.0000 Uani . . . . . .
C20 C -0.2786(3) 0.3150(3) 0.5168(3) 0.0229 1.0000 Uani . . . . . .
C21 C -0.4764(4) 0.6370(3) 0.7607(3) 0.0323 1.0000 Uani . . . . . .
H71 H 0.5946 0.3881 0.8921 0.0287 1.0000 Uiso R . . . . .
H72 H 0.6710 0.2885 0.7626 0.0295 1.0000 Uiso R . . . . .
H83 H 0.8759 0.3908 0.9364 0.0549 1.0000 Uiso R . . . . .
H82 H 0.7866 0.3219 1.0202 0.0550 1.0000 Uiso R . . . . .
H81 H 0.8622 0.2213 0.8924 0.0541 1.0000 Uiso R . . . . .
H101 H 0.3418 -0.0714 0.9313 0.0391 1.0000 Uiso R . . . . .
H102 H 0.2474 0.0722 0.9685 0.0392 1.0000 Uiso R . . . . .
H113 H 0.0626 -0.1292 0.9347 0.0548 1.0000 Uiso R . . . . .
H112 H 0.1135 -0.2096 0.7897 0.0544 1.0000 Uiso R . . . . .
H111 H 0.0194 -0.0662 0.8305 0.0552 1.0000 Uiso R . . . . .
H142 H 0.0712 0.2852 0.4490 0.0392 1.0000 Uiso R . . . . .
H141 H -0.0468 0.1482 0.4326 0.0383 1.0000 Uiso R . . . . .
H161 H 0.0403 0.4960 0.7125 0.0322 1.0000 Uiso R . . . . .
H171 H -0.1551 0.6481 0.8160 0.0316 1.0000 Uiso R . . . . .
H191 H -0.5052 0.3883 0.5463 0.0270 1.0000 Uiso R . . . . .
H201 H -0.3103 0.2292 0.4416 0.0269 1.0000 Uiso R . . . . .
H212 H -0.5842 0.5953 0.7246 0.0478 1.0000 Uiso R . . . . .
H213 H -0.4685 0.6576 0.8515 0.0482 1.0000 Uiso R . . . . .
H211 H -0.4596 0.7289 0.7520 0.0484 1.0000 Uiso R . . . . .
H131 H 0.1015 0.2401 0.6684 0.0325 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          6.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ni1 . C3 2_656 2.502(3) yes
Ni1 . N4 2_656 1.911(2) yes
Ni1 . S2 2_656 2.2262(6) yes
Ni1 . P5 2_656 3.2506(6) yes
Ni1 . S2 . 2.2262(6) yes
Ni1 . C3 . 2.502(3) yes
Ni1 . N4 . 1.911(2) yes
Ni1 . P5 . 3.2506(6) yes
S2 . C3 . 1.729(3) yes
C3 . N4 . 1.348(4) yes
C3 . N13 . 1.316(4) yes
N4 . P5 . 1.646(2) yes
P5 . O6 . 1.5724(19) yes
P5 . O9 . 1.576(2) yes
P5 . S12 . 1.9370(9) yes
O6 . C7 . 1.468(3) yes
C7 . C8 . 1.491(4) yes
C7 . H71 . 0.971 no
C7 . H72 . 0.971 no
C8 . H83 . 0.949 no
C8 . H82 . 0.970 no
C8 . H81 . 0.970 no
O9 . C10 . 1.452(3) yes
C10 . C11 . 1.492(5) yes
C10 . H101 . 0.972 no
C10 . H102 . 0.963 no
C11 . H113 . 0.965 no
C11 . H112 . 0.974 no
C11 . H111 . 0.960 no
N13 . C14 . 1.465(4) yes
N13 . H131 . 0.862 no
C14 . C15 . 1.511(4) yes
C14 . H142 . 0.959 no
C14 . H141 . 0.973 no
C15 . C16 . 1.399(4) yes
C15 . C20 . 1.386(4) yes
C16 . C17 . 1.382(4) yes
C16 . H161 . 0.940 no
C17 . C18 . 1.392(4) yes
C17 . H171 . 0.928 no
C18 . C19 . 1.392(4) yes
C18 . C21 . 1.507(4) yes
C19 . C20 . 1.387(4) yes
C19 . H191 . 0.939 no
C20 . H201 . 0.938 no
C21 . H212 . 0.951 no
C21 . H213 . 0.947 no
C21 . H211 . 0.965 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 2_656 Ni1 . N4 2_656 32.15(9) yes
C3 2_656 Ni1 . S2 2_656 42.41(6) yes
N4 2_656 Ni1 . S2 2_656 74.56(7) yes
C3 2_656 Ni1 . P5 2_656 54.13(6) yes
N4 2_656 Ni1 . P5 2_656 22.12(7) yes
S2 2_656 Ni1 . P5 2_656 96.499(19) yes
C3 2_656 Ni1 . S2 . 137.59(6) yes
N4 2_656 Ni1 . S2 . 105.44(7) yes
S2 2_656 Ni1 . S2 . 179.99 yes
P5 2_656 Ni1 . S2 . 83.501(19) yes
C3 2_656 Ni1 . C3 . 180.00 yes
N4 2_656 Ni1 . C3 . 147.85(9) yes
S2 2_656 Ni1 . C3 . 137.59(6) yes
P5 2_656 Ni1 . C3 . 125.87(6) yes
S2 . Ni1 . C3 . 42.41(6) yes
C3 2_656 Ni1 . N4 . 147.85(9) yes
N4 2_656 Ni1 . N4 . 179.99 yes
S2 2_656 Ni1 . N4 . 105.44(7) yes
P5 2_656 Ni1 . N4 . 157.88(7) yes
S2 . Ni1 . N4 . 74.56(7) yes
C3 2_656 Ni1 . P5 . 125.87(6) yes
N4 2_656 Ni1 . P5 . 157.88(7) yes
S2 2_656 Ni1 . P5 . 83.501(19) yes
P5 2_656 Ni1 . P5 . 180.00 yes
S2 . Ni1 . P5 . 96.499(19) yes
C3 . Ni1 . N4 . 32.15(9) yes
C3 . Ni1 . P5 . 54.13(6) yes
N4 . Ni1 . P5 . 22.12(7) yes
Ni1 . S2 . C3 . 77.35(9) yes
Ni1 . C3 . S2 . 60.24(8) yes
Ni1 . C3 . N4 . 48.98(12) yes
S2 . C3 . N4 . 109.22(19) yes
Ni1 . C3 . N13 . 175.4(2) yes
S2 . C3 . N13 . 124.0(2) yes
N4 . C3 . N13 . 126.8(2) yes
C3 . N4 . Ni1 . 98.87(16) yes
C3 . N4 . P5 . 128.61(19) yes
Ni1 . N4 . P5 . 131.96(13) yes
N4 . P5 . Ni1 . 25.92(8) yes
N4 . P5 . O6 . 105.85(11) yes
Ni1 . P5 . O6 . 85.18(7) yes
N4 . P5 . O9 . 102.68(11) yes
Ni1 . P5 . O9 . 91.73(7) yes
O6 . P5 . O9 . 100.80(11) yes
N4 . P5 . S12 . 116.36(8) yes
Ni1 . P5 . S12 . 141.21(4) yes
O6 . P5 . S12 . 113.91(8) yes
O9 . P5 . S12 . 115.43(9) yes
P5 . O6 . C7 . 118.87(15) yes
O6 . C7 . C8 . 107.4(2) yes
O6 . C7 . H71 . 110.4 no
C8 . C7 . H71 . 110.0 no
O6 . C7 . H72 . 108.4 no
C8 . C7 . H72 . 111.6 no
H71 . C7 . H72 . 109.0 no
C7 . C8 . H83 . 109.2 no
C7 . C8 . H82 . 111.7 no
H83 . C8 . H82 . 108.8 no
C7 . C8 . H81 . 110.5 no
H83 . C8 . H81 . 108.6 no
H82 . C8 . H81 . 107.9 no
P5 . O9 . C10 . 123.07(18) yes
O9 . C10 . C11 . 107.7(2) yes
O9 . C10 . H101 . 108.4 no
C11 . C10 . H101 . 110.8 no
O9 . C10 . H102 . 108.4 no
C11 . C10 . H102 . 111.4 no
H101 . C10 . H102 . 110.0 no
C10 . C11 . H113 . 109.0 no
C10 . C11 . H112 . 110.2 no
H113 . C11 . H112 . 109.9 no
C10 . C11 . H111 . 110.0 no
H113 . C11 . H111 . 108.3 no
H112 . C11 . H111 . 109.5 no
C3 . N13 . C14 . 122.7(2) yes
C3 . N13 . H131 . 117.0 no
C14 . N13 . H131 . 120.1 no
N13 . C14 . C15 . 111.3(2) yes
N13 . C14 . H142 . 107.4 no
C15 . C14 . H142 . 108.4 no
N13 . C14 . H141 . 109.8 no
C15 . C14 . H141 . 110.5 no
H142 . C14 . H141 . 109.4 no
C14 . C15 . C16 . 122.0(3) yes
C14 . C15 . C20 . 119.6(2) yes
C16 . C15 . C20 . 118.4(2) yes
C15 . C16 . C17 . 120.4(3) yes
C15 . C16 . H161 . 120.2 no
C17 . C16 . H161 . 119.4 no
C16 . C17 . C18 . 121.5(3) yes
C16 . C17 . H171 . 119.7 no
C18 . C17 . H171 . 118.8 no
C17 . C18 . C19 . 117.7(2) yes
C17 . C18 . C21 . 121.0(3) yes
C19 . C18 . C21 . 121.2(3) yes
C18 . C19 . C20 . 121.1(3) yes
C18 . C19 . H191 . 118.2 no
C20 . C19 . H191 . 120.7 no
C19 . C20 . C15 . 120.8(2) yes
C19 . C20 . H201 . 120.2 no
C15 . C20 . H201 . 118.9 no
C18 . C21 . H212 . 111.2 no
C18 . C21 . H213 . 111.4 no
H212 . C21 . H213 . 108.1 no
C18 . C21 . H211 . 109.8 no
H212 . C21 . H211 . 108.5 no
H213 . C21 . H211 . 107.7 no



# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
9 -2 2 x .
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.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_I_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2311921'
loop_
_audit_author_name
_audit_author_address
'Eliska Zmeskalova'
;Institute of Physics of the Czech Academy of Sciences
Czech Republic
;
_audit_update_record             
;
2023-12-04 deposited with the CCDC.	2024-09-26 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;

_refine_special_details          
; 
 ? 
;

#--------------------------------------------------------------- 
# _oxford_ data items, April 2010: 
# There is some uncertainty about the correct way of forming local data 
# names, e.g. 

# _atom_site_special_shape_oxford 
# or 
# _oxford_atom_site_special_shape 

# see: 
# http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace 

# A reserved prefix, e.g. foo, must be used in the following way 
# " If the data file contains items defined in a DDL1 dictionary, the 
# local data names assigned under the reserved prefix must contain it as 
# their first component, e.g. _foo_atom_site_my_item. " 

# However, this seems to say the opposite: 
# http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html 

# According to advice from the IUCr, CRYSTALS is correct 
#--------------------------------------------------------------- 
# End of 'script/refcif.dat' 
#end of refcif 
_cell_length_a                   5.8046(2)
_cell_length_b                   10.7878(2)
_cell_length_c                   13.3907(3)
_cell_angle_alpha                81.0002(18)
_cell_angle_beta                 83.334(2)
_cell_angle_gamma                89.276(2)
_cell_volume                     822.58(4)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.2955 0.4335 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C12 H20 N2 O2 P1 S2 
# Dc =      1.29 Fooo =    338.00 Mu =     38.58 M =    319.41
# Found Formula = C13 H21 N2 O2 P1 S2 
# Dc =      1.34 FOOO =    352.00 Mu =     38.80 M =    332.43

_chemical_formula_sum            'C13 H21 N2 O2 P1 S2'
_chemical_formula_moiety         'C13 H21 N2 O2 P1 S2'
_chemical_compound_source        .
_chemical_formula_weight         332.43


_cell_measurement_reflns_used    8960
_cell_measurement_theta_min      3.33
_cell_measurement_theta_max      67.67
_cell_measurement_temperature    120

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.383
_exptl_crystal_size_mid          0.545
_exptl_crystal_size_max          0.791

_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             352
_exptl_absorpt_coefficient_mu    3.880

# Sheldrick geometric approximatio 0.12 0.23 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.10
_exptl_absorpt_correction_T_max  0.23
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      120
_diffrn_reflns_number            13323
_diffrn_reflns_av_unetI/netI     0.048
_reflns_number_total             2929
_diffrn_reflns_av_R_equivalents  0.038
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2929 
# Theoretical number of reflections is about 5941 


_diffrn_reflns_theta_min         3.364
_diffrn_reflns_theta_max         67.579
_diffrn_measured_fraction_theta_max 0.991

_diffrn_reflns_theta_full        67.579
_diffrn_measured_fraction_theta_full 0.991


_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -6
_reflns_limit_h_max              6
_reflns_limit_k_min              -12
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              16

_oxford_diffrn_Wilson_B_factor   1.27
_oxford_diffrn_Wilson_scale      0.01

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.37
_refine_diff_density_max         0.36


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     8
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2929
_oxford_refine_ls_R_factor_ref   0.0328
_refine_ls_R_factor_all          0.0328
_refine_ls_wR_factor_ref         0.0965
_refine_ls_wR_factor_all         0.0965
_refine_ls_goodness_of_fit_ref   1.0378
_refine_ls_shift/su_max          0.0005866
_refine_ls_shift/su_mean         0.0000358


# Computed with I/sigma = -10 
_oxford_reflns_number_all        2929
_oxford_refine_ls_R_factor_all   0.0328
_oxford_refine_ls_wR_factor_all  0.0965

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2793
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_gt          0.0877


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.06P)² + 0.53P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
S1 S 0.39373(8) 0.73386(4) 0.27678(3) 0.0198 1.0000 Uani . . . . . .
P2 P 0.21353(8) 0.73693(4) 0.16424(3) 0.0135 1.0000 Uani D . . . . .
O3 O 0.3470(2) 0.70851(12) 0.06168(9) 0.0170 1.0000 Uani . . . . . .
C4 C 0.5834(3) 0.75566(19) 0.02594(14) 0.0210 1.0000 Uani . . . . . .
C5 C 0.6730(4) 0.6885(2) -0.06018(17) 0.0341 1.0000 Uani . . . . . .
O6 O 0.0035(2) 0.64272(11) 0.18157(10) 0.0184 1.0000 Uani . . . . . .
C7 C 0.0208(4) 0.51410(17) 0.23382(15) 0.0227 1.0000 Uani . . . . . .
C8 C -0.1742(4) 0.4399(2) 0.20809(19) 0.0321 1.0000 Uani . . . . . .
N9 N 0.0840(3) 0.87290(14) 0.12721(11) 0.0152 1.0000 Uani D . . . . .
C10 C -0.0547(3) 0.94657(16) 0.18424(13) 0.0151 1.0000 Uani D . . . . .
S11 S -0.19687(9) 1.06870(4) 0.12602(3) 0.0222 1.0000 Uani . . . . . .
N12 N -0.0698(3) 0.91535(14) 0.28541(11) 0.0154 1.0000 Uani D . . . . .
C13 C -0.1963(3) 0.98817(17) 0.35591(13) 0.0165 1.0000 Uani D . . . . .
C14 C -0.0564(3) 1.09523(16) 0.37981(13) 0.0143 1.0000 Uani . . . . . .
C15 C 0.1649(3) 1.12648(17) 0.33216(13) 0.0166 1.0000 Uani . . . . . .
C16 C 0.2885(3) 1.22367(18) 0.35857(14) 0.0186 1.0000 Uani . . . . . .
C17 C 0.1947(4) 1.29308(17) 0.43251(14) 0.0183 1.0000 Uani . . . . . .
C18 C 0.3316(4) 1.39558(18) 0.46351(16) 0.0256 1.0000 Uani . . . . . .
C19 C -0.0293(4) 1.26286(17) 0.47878(13) 0.0192 1.0000 Uani . . . . . .
C20 C -0.1525(3) 1.16525(17) 0.45350(13) 0.0170 1.0000 Uani . . . . . .
H41 H 0.5841 0.8460 0.0029 0.0242 1.0000 Uiso R . . . . .
H42 H 0.6790 0.7353 0.0812 0.0244 1.0000 Uiso R . . . . .
H52 H 0.8265 0.7196 -0.0873 0.0500 1.0000 Uiso R . . . . .
H53 H 0.5739 0.7010 -0.1125 0.0506 1.0000 Uiso R . . . . .
H51 H 0.6774 0.6018 -0.0347 0.0509 1.0000 Uiso R . . . . .
H71 H -0.0023 0.5156 0.3074 0.0275 1.0000 Uiso R . . . . .
H72 H 0.1734 0.4796 0.2106 0.0257 1.0000 Uiso R . . . . .
H82 H -0.1739 0.3550 0.2460 0.0473 1.0000 Uiso R . . . . .
H83 H -0.3222 0.4787 0.2251 0.0465 1.0000 Uiso R . . . . .
H81 H -0.1518 0.4385 0.1340 0.0473 1.0000 Uiso R . . . . .
H132 H -0.3351 1.0222 0.3259 0.0176 1.0000 Uiso R . . . . .
H131 H -0.2399 0.9290 0.4207 0.0195 1.0000 Uiso R . . . . .
H151 H 0.2335 1.0770 0.2828 0.0185 1.0000 Uiso R . . . . .
H161 H 0.4405 1.2452 0.3245 0.0227 1.0000 Uiso R . . . . .
H181 H 0.2328 1.4558 0.4916 0.0388 1.0000 Uiso R . . . . .
H183 H 0.4254 1.4378 0.4051 0.0408 1.0000 Uiso R . . . . .
H182 H 0.4318 1.3626 0.5105 0.0394 1.0000 Uiso R . . . . .
H191 H -0.0986 1.3109 0.5268 0.0227 1.0000 Uiso R . . . . .
H201 H -0.3031 1.1427 0.4886 0.0206 1.0000 Uiso R . . . . .
H121 H 0.028(3) 0.8616(18) 0.3088(12) 0.0181(19) 1.0000 Uiso D . . . . .
H91 H 0.100(4) 0.8992(16) 0.0628(12) 0.0191(19) 1.0000 Uiso D . . . . .

_refine_ls_extinction_coef       23(3)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          10.4(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . P2 . 1.9276(6) yes
P2 . O3 . 1.5682(13) yes
P2 . O6 . 1.5700(13) yes
P2 . N9 . 1.6714(15) yes
O3 . C4 . 1.470(2) yes
C4 . C5 . 1.496(3) yes
C4 . H41 . 0.975 no
C4 . H42 . 0.972 no
C5 . H52 . 0.966 no
C5 . H53 . 0.950 no
C5 . H51 . 0.945 no
O6 . C7 . 1.461(2) yes
C7 . C8 . 1.496(3) yes
C7 . H71 . 0.981 no
C7 . H72 . 0.992 no
C8 . H82 . 0.976 no
C8 . H83 . 0.969 no
C8 . H81 . 0.988 no
N9 . C10 . 1.376(2) yes
N9 . H91 . 0.859(16) no
C10 . S11 . 1.6807(18) yes
C10 . N12 . 1.337(2) yes
N12 . C13 . 1.450(2) yes
N12 . H121 . 0.857(16) no
C13 . C14 . 1.515(2) yes
C13 . H132 . 0.984 no
C13 . H131 . 1.003 no
C14 . C15 . 1.387(3) yes
C14 . C20 . 1.397(2) yes
C15 . C16 . 1.390(3) yes
C15 . H151 . 0.961 no
C16 . C17 . 1.391(3) yes
C16 . H161 . 0.958 no
C17 . C18 . 1.506(3) yes
C17 . C19 . 1.393(3) yes
C18 . H181 . 0.953 no
C18 . H183 . 0.955 no
C18 . H182 . 0.932 no
C19 . C20 . 1.386(3) yes
C19 . H191 . 0.940 no
C20 . H201 . 0.958 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
S1 . P2 . O3 . 116.52(5) yes
S1 . P2 . O6 . 116.08(5) yes
O3 . P2 . O6 . 102.54(7) yes
S1 . P2 . N9 . 115.87(6) yes
O3 . P2 . N9 . 102.11(7) yes
O6 . P2 . N9 . 101.44(7) yes
P2 . O3 . C4 . 121.85(11) yes
O3 . C4 . C5 . 106.86(16) yes
O3 . C4 . H41 . 111.2 no
C5 . C4 . H41 . 110.1 no
O3 . C4 . H42 . 108.7 no
C5 . C4 . H42 . 109.5 no
H41 . C4 . H42 . 110.3 no
C4 . C5 . H52 . 109.1 no
C4 . C5 . H53 . 110.9 no
H52 . C5 . H53 . 109.5 no
C4 . C5 . H51 . 108.0 no
H52 . C5 . H51 . 110.6 no
H53 . C5 . H51 . 108.8 no
P2 . O6 . C7 . 121.92(12) yes
O6 . C7 . C8 . 107.73(16) yes
O6 . C7 . H71 . 108.0 no
C8 . C7 . H71 . 107.8 no
O6 . C7 . H72 . 108.8 no
C8 . C7 . H72 . 111.2 no
H71 . C7 . H72 . 113.1 no
C7 . C8 . H82 . 109.6 no
C7 . C8 . H83 . 110.8 no
H82 . C8 . H83 . 109.0 no
C7 . C8 . H81 . 108.0 no
H82 . C8 . H81 . 110.8 no
H83 . C8 . H81 . 108.6 no
P2 . N9 . C10 . 129.50(13) yes
P2 . N9 . H91 . 115.7(10) no
C10 . N9 . H91 . 114.7(10) no
N9 . C10 . S11 . 119.95(13) yes
N9 . C10 . N12 . 116.95(16) yes
S11 . C10 . N12 . 123.11(14) yes
C10 . N12 . C13 . 123.59(15) yes
C10 . N12 . H121 . 116.7(11) no
C13 . N12 . H121 . 117.7(11) no
N12 . C13 . C14 . 113.68(15) yes
N12 . C13 . H132 . 107.9 no
C14 . C13 . H132 . 109.2 no
N12 . C13 . H131 . 106.7 no
C14 . C13 . H131 . 108.4 no
H132 . C13 . H131 . 111.0 no
C13 . C14 . C15 . 122.83(16) yes
C13 . C14 . C20 . 118.93(16) yes
C15 . C14 . C20 . 118.24(16) yes
C14 . C15 . C16 . 120.64(17) yes
C14 . C15 . H151 . 118.5 no
C16 . C15 . H151 . 120.8 no
C15 . C16 . C17 . 121.42(18) yes
C15 . C16 . H161 . 120.0 no
C17 . C16 . H161 . 118.6 no
C16 . C17 . C18 . 121.37(19) yes
C16 . C17 . C19 . 117.71(17) yes
C18 . C17 . C19 . 120.90(18) yes
C17 . C18 . H181 . 111.7 no
C17 . C18 . H183 . 109.2 no
H181 . C18 . H183 . 108.3 no
C17 . C18 . H182 . 111.1 no
H181 . C18 . H182 . 109.3 no
H183 . C18 . H182 . 107.0 no
C17 . C19 . C20 . 121.12(17) yes
C17 . C19 . H191 . 119.1 no
C20 . C19 . H191 . 119.8 no
C14 . C20 . C19 . 120.85(17) yes
C14 . C20 . H201 . 119.0 no
C19 . C20 . H201 . 120.1 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C4 . H42 . O6 1_655 161 0.97 2.54 3.476(3) yes


# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
