# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_ROY_ON_0p02GPa
_database_code_depnum_ccdc_archive 'CCDC 2098636'
loop_
_audit_author_name
_audit_author_address
'Nicholas Funnell'
;STFC, ISIS Neutron Facility
United Kingdom
;
_audit_update_record             
;
2021-07-22 deposited with the CCDC.	2021-08-27 downloaded from the CCDC.
;
_audit_creation_date             2021-01-25
_audit_creation_method           'CRYSTALS_ver_14.61_build_7795 '


_chemical_name_systematic        
;
5-methyl-2[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
;


# CheckCIF alerts
_vrf_THETM01_ROY_ON_0p02GPa      
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below. 
;
_vrf_PLAT027_ROY_ON_0p02GPa      
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      17.44 Degree
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below. 
;
_vrf_PLAT029_ROY_ON_0p02GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.727 Why?  
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below.  
;
_vrf_PLAT201_ROY_ON_0p02GPa      
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         17 Report
RESPONSE: The model could only be refined isotropically in order to maintain a 
favourable data-to-parameter ratio, due to numerous unmeasured reflections.
The relatively electron-rich sulfur atom has been modelled anisotropically.
;
_vrf_PLAT340_ROY_ON_0p02GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01236 Ang.  
RESPONSE: These are poor-quality diffraction data.
;
_vrf_PLAT911_ROY_ON_0p02GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.555        473 Report
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below. 
;
_vrf_PLAT082_ROY_ON_0p02GPa      
;
PROBLEM: High R1 Value ..................................       0.15 Report
RESPONSE: These are poor-quality diffraction data and the model has only been 
refined isotropically.
;
_vrf_PLAT910_ROY_ON_0p02GPa      
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).          8 Note  
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below. 
;

_refine_special_details          
; 
In the absence of significant anomalous scattering, Friedel pairs were 
merged. 

Data were collected in a Merrill-Bassett diamond anvil cell, which 
significantly restricts the regions over which reciprocal space can be sampled. 
Thus, these data are poor quality/incomplete, reflected in numerous CheckCIF 
alerts regarding refinement statistics. At all pressures, the atomic 
connectivity is known.

All non-sulfur atoms were refined isotropically; sulfur was refined 
anisotropically. Hydrogen atoms were constrained to ride on their host atoms.

#===============================================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#===============================================================================
Theta sin(th)/Lambda Complete  Expected Measured Total Missing
#-------------------------------------------------------------------------------
 20.82     0.500     0.728         1231      896      335
 23.01     0.550     0.713         1632     1163      469
 23.25     0.555     0.712         1672     1191      481
------------------------------------------------------------ ACTA Min. Res. ---

Note: The Reported Completeness refers to the Actual H,K,L Index Range 
;


#end of refcif 
_cell_length_a                   3.920050(19)
_cell_length_b                   18.56291(5)
_cell_length_c                   16.40883(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.655(6)
_cell_angle_gamma                90
_cell_volume                     1191.601(11)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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 0.1246 0.1234 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            4

# Given Formula = C12 H9 N3 O2 S1 
# Dc =      1.45 Fooo =    536.00 Mu =      2.68 M =    259.29
# Found Formula = C12 H9 N3 O2 S1 
# Dc =      1.45 FOOO =    536.00 Mu =      2.68 M =    259.29

_chemical_formula_sum            'C12 H9 N3 O2 S1'
_chemical_formula_moiety         'C12 H9 N3 O2 S1'
_chemical_compound_source        'TCI Chemicals'
_chemical_formula_weight         259.29


_cell_measurement_reflns_used    1582
_cell_measurement_theta_min      1.65
_cell_measurement_theta_max      22.15
_cell_measurement_temperature    293

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_max          0.248

_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.268

# Sheldrick geometric approximatio 0.98 0.99 
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_absorpt_correction_T_min  0.09
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Model from previously-determined structure'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      293
_diffrn_reflns_number            3968
_diffrn_reflns_av_unetI/netI     0.065
_reflns_number_total             1201
_diffrn_reflns_av_R_equivalents  0.068
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1201 
# Theoretical number of reflections is about 3421 


_diffrn_reflns_theta_min         1.658
_diffrn_reflns_theta_max         23.252
_diffrn_measured_fraction_theta_max 0.699

_diffrn_reflns_theta_full        17.439
_diffrn_measured_fraction_theta_full 0.727


_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -4
_reflns_limit_h_max              4
_reflns_limit_k_min              0
_reflns_limit_k_max              18
_reflns_limit_l_min              0
_reflns_limit_l_max              16

_oxford_diffrn_Wilson_B_factor   5.12
_oxford_diffrn_Wilson_scale      5.48

_atom_sites_solution_primary     geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -1.09
_refine_diff_density_max         0.99


# 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     94
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1191
_oxford_refine_ls_R_factor_ref   0.2379
_refine_ls_R_factor_all          0.2379
_refine_ls_wR_factor_ref         0.0829
_refine_ls_wR_factor_all         0.0829
_refine_ls_goodness_of_fit_ref   0.9062
_refine_ls_shift/su_max          0.0001567
_refine_ls_shift/su_mean         0.0000411


# Computed with I/sigma = -10 
_oxford_reflns_number_all        1191
_oxford_refine_ls_R_factor_all   0.2379
_oxford_refine_ls_wR_factor_all  0.0829

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                662
_refine_ls_R_factor_gt           0.1525
_refine_ls_wR_factor_gt          0.0718


_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      sigma
_refine_ls_weighting_details     
;
 Method= 
 SQRT(W) = 1/(Data with the key SIGMA(/FO/) in list 6) 
;

# 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 0.8453(6) 0.59696(13) 0.42922(16) 0.0694 1.0000 Uani D U . . . .
O1 O 0.5061(12) 0.6178(3) 0.0298(4) 0.0788(19) 1.0000 Uiso D U . . . .
O2 O 0.5900(14) 0.6889(3) 0.1346(4) 0.0792(17) 1.0000 Uiso D U . . . .
C1 C 0.9395(16) 0.5807(5) 0.2234(6) 0.0690(17) 1.0000 Uiso D U . . . .
C2 C 1.1230(18) 0.5224(5) 0.2624(6) 0.0681(18) 1.0000 Uiso D U . . . .
C3 C 1.1652(18) 0.4616(5) 0.2176(6) 0.0678(19) 1.0000 Uiso D U . . . .
C4 C 1.0334(16) 0.4544(4) 0.1379(6) 0.0684(19) 1.0000 Uiso D U . . . .
C5 C 0.8590(18) 0.5096(4) 0.0997(6) 0.0702(18) 1.0000 Uiso D U . . . .
C6 C 0.8146(17) 0.5722(5) 0.1450(6) 0.0715(17) 1.0000 Uiso D U . . . .
C7 C 0.9687(17) 0.6549(4) 0.3547(6) 0.0648(17) 1.0000 Uiso D U . . . .
C8 C 1.1236(17) 0.7138(4) 0.3860(6) 0.0660(17) 1.0000 Uiso D U . . . .
C9 C 1.1448(18) 0.7136(4) 0.4744(6) 0.0656(18) 1.0000 Uiso D U . . . .
C10 C 1.0077(12) 0.6557(3) 0.5057(6) 0.0665(17) 1.0000 Uiso D U . . . .
C11 C 0.9802(12) 0.6358(3) 0.5929(5) 0.071(2) 1.0000 Uiso D U . . . .
C12 C 1.2666(18) 0.7640(5) 0.3337(6) 0.0656(18) 1.0000 Uiso D U . . . .
N1 N 0.9001(14) 0.6410(4) 0.2726(5) 0.0675(16) 1.0000 Uiso D U . . . .
N2 N 1.3954(17) 0.8025(4) 0.2897(5) 0.0708(18) 1.0000 Uiso D U . . . .
N3 N 0.6246(17) 0.6297(4) 0.1004(5) 0.0751(18) 1.0000 Uiso D U . . . .
H1 H 0.788(6) 0.6745(17) 0.2473(19) 0.083(3) 1.0000 Uiso D . . . . .
H2 H 1.2110 0.5259 0.3158 0.0979 1.0000 Uiso R . . . . .
H3 H 1.2877 0.4241 0.2424 0.0949 1.0000 Uiso R . . . . .
H4 H 1.0634 0.4117 0.1092 0.0979 1.0000 Uiso R . . . . .
H5 H 0.7719 0.5068 0.0457 0.0939 1.0000 Uiso R . . . . .
H9 H 1.2434 0.7510 0.5059 0.0970 1.0000 Uiso R . . . . .
H111 H 1.1859 0.6084 0.6125 0.1829 1.0000 Uiso DR . . . . .
H112 H 0.9622 0.6799 0.6258 0.1829 1.0000 Uiso DR . . . . .
H113 H 0.7746 0.6058 0.5981 0.1831 1.0000 Uiso DR . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.4448(18)
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 . C7 . 1.721(9) yes
S1 . C10 . 1.751(8) yes
O1 . N3 . 1.240(8) yes
O2 . N3 . 1.245(8) yes
C1 . C2 . 1.429(12) yes
C1 . C6 . 1.356(11) yes
C1 . N1 . 1.394(11) yes
C2 . C3 . 1.362(11) yes
C2 . H2 . 0.923 no
C3 . C4 . 1.383(11) yes
C3 . H3 . 0.925 no
C4 . C5 . 1.362(10) yes
C4 . H4 . 0.933 no
C5 . C6 . 1.398(12) yes
C5 . H5 . 0.930 no
C6 . N3 . 1.470(10) yes
C7 . C8 . 1.337(11) yes
C7 . N1 . 1.380(10) yes
C8 . C9 . 1.449(11) yes
C8 . C12 . 1.407(11) yes
C9 . C10 . 1.320(9) yes
C9 . H9 . 0.934 no
C10 . C11 . 1.488(11) yes
C11 . H111 . 0.990 no
C11 . H112 . 0.986 no
C11 . H113 . 0.988 no
C12 . N2 . 1.155(11) yes
N1 . H1 . 0.85(3) 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
C7 . S1 . C10 . 90.8(5) yes
C2 . C1 . C6 . 118.5(8) yes
C2 . C1 . N1 . 114.9(9) yes
C6 . C1 . N1 . 126.6(8) yes
C1 . C2 . C3 . 117.4(9) yes
C1 . C2 . H2 . 121.2 no
C3 . C2 . H2 . 121.3 no
C2 . C3 . C4 . 122.7(8) yes
C2 . C3 . H3 . 117.5 no
C4 . C3 . H3 . 119.7 no
C3 . C4 . C5 . 120.6(9) yes
C3 . C4 . H4 . 120.6 no
C5 . C4 . H4 . 118.9 no
C4 . C5 . C6 . 117.2(10) yes
C4 . C5 . H5 . 122.6 no
C6 . C5 . H5 . 120.2 no
C5 . C6 . C1 . 123.5(8) yes
C5 . C6 . N3 . 114.5(10) yes
C1 . C6 . N3 . 122.0(8) yes
S1 . C7 . C8 . 112.3(8) yes
S1 . C7 . N1 . 122.0(6) yes
C8 . C7 . N1 . 125.7(8) yes
C7 . C8 . C9 . 112.3(8) yes
C7 . C8 . C12 . 119.8(9) yes
C9 . C8 . C12 . 127.7(8) yes
C8 . C9 . C10 . 113.1(7) yes
C8 . C9 . H9 . 123.1 no
C10 . C9 . H9 . 123.7 no
S1 . C10 . C9 . 111.5(8) yes
S1 . C10 . C11 . 119.3(3) yes
C9 . C10 . C11 . 129.2(6) yes
C10 . C11 . H111 . 109.5 no
C10 . C11 . H112 . 109.5 no
H111 . C11 . H112 . 109.5 no
C10 . C11 . H113 . 109.5 no
H111 . C11 . H113 . 109.5 no
H112 . C11 . H113 . 109.5 no
C8 . C12 . N2 . 176.4(11) yes
C1 . N1 . C7 . 133.8(8) yes
C1 . N1 . H1 . 112(2) no
C7 . N1 . H1 . 114(2) no
C6 . N3 . O2 . 118.8(9) yes
C6 . N3 . O1 . 119.0(8) yes
O2 . N3 . O1 . 122.2(7) yes
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
N1 . H1 . O2 . 135(3) 0.85(3) 1.98(3) 2.654(11) yes



# 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
0 12 3 x .
-1 6 1 x .
1 2 7 x .
0 2 5 x .
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_chemical_name_common            ROY
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_ROY_ON_0p62GPa
_database_code_depnum_ccdc_archive 'CCDC 2098637'
loop_
_audit_author_name
_audit_author_address
'Nicholas Funnell'
;STFC, ISIS Neutron Facility
United Kingdom
;
_audit_update_record             
;
2021-07-22 deposited with the CCDC.	2021-08-27 downloaded from the CCDC.
;
_audit_creation_date             2021-01-25
_audit_creation_method           'CRYSTALS_ver_14.61_build_7795 '


_chemical_name_systematic        
;
5-methyl-2[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
;


# CheckCIF alerts
_vrf_THETM01_ROY_ON_0p62GPa      
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below.  
;
_vrf_PLAT027_ROY_ON_0p62GPa      
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      17.44 Degree
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below. 
;
_vrf_PLAT029_ROY_ON_0p62GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.725 Why?  
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below. 
;
_vrf_PLAT201_ROY_ON_0p62GPa      
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         17 Report
RESPONSE: The model could only be refined isotropically in order to maintain a 
favourable data-to-parameter ratio, due to numerous unmeasured reflections.
The relatively electron-rich sulfur atom has been modelled anisotropically.
;
_vrf_PLAT911_ROY_ON_0p62GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.556        425 Report
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below. 
;
_vrf_PLAT082_ROY_ON_0p62GPa      
;
PROBLEM: High R1 Value ..................................       0.11 Report
RESPONSE: These are poor-quality diffraction data and the model has only been 
refined isotropically.
;
_vrf_PLAT340_ROY_ON_0p62GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00864 Ang.  
RESPONSE: These are poor-quality diffraction data.
;
_vrf_PLAT910_ROY_ON_0p62GPa      
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).          8 Note  
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below.  
;
# end Validation Reply Form


_refine_special_details          
; 
In the absence of significant anomalous scattering, Friedel pairs were 
merged. 

Data were collected in a Merrill-Bassett diamond anvil cell, which 
significantly restricts the regions over which reciprocal space can be sampled. 
Thus, these data are poor quality/incomplete, reflected in numerous CheckCIF 
alerts regarding refinement statistics. At all pressures, the atomic 
connectivity is known.

All non-sulfur atoms were refined isotropically; sulfur was refined 
anisotropically. Hydrogen atoms were constrained to ride on their host atoms.

#===============================================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#===============================================================================
Theta sin(th)/Lambda Complete  Expected Measured Total Missing
#-------------------------------------------------------------------------------
 20.82     0.500     0.725         1161      842      319
 23.01     0.550     0.715         1486     1062      424
 23.25     0.556     0.717         1528     1095      433
------------------------------------------------------------ ACTA Min. Res. ---

Note: The Reported Completeness refers to the Actual H,K,L Index Range
;


#end of refcif 
_cell_length_a                   3.767380(17)
_cell_length_b                   18.14088(5)
_cell_length_c                   16.22092(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.918(5)
_cell_angle_gamma                90
_cell_volume                     1107.975(8)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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 0.1246 0.1234 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            4

# Given Formula = C12 H9 N3 O2 S1 
# Dc =      1.55 Fooo =    536.00 Mu =      2.89 M =    259.29
# Found Formula = C12 H9 N3 O2 S1 
# Dc =      1.55 FOOO =    536.00 Mu =      2.89 M =    259.29

_chemical_formula_sum            'C12 H9 N3 O2 S1'
_chemical_formula_moiety         'C12 H9 N3 O2 S1'
_chemical_compound_source        'TCI Chemicals'
_chemical_formula_weight         259.29


_cell_measurement_reflns_used    1869
_cell_measurement_theta_min      1.68
_cell_measurement_theta_max      23.25
_cell_measurement_temperature    293

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_max          0.248

_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.289

# Sheldrick geometric approximatio 0.98 0.99 
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_absorpt_correction_T_min  0.19
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Model from previously-determined structure'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      293
_diffrn_ambient_pressure         620000
_diffrn_reflns_number            3792
_diffrn_reflns_av_unetI/netI     0.056
_reflns_number_total             1103
_diffrn_reflns_av_R_equivalents  0.053
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1103 
# Theoretical number of reflections is about 3182 


_diffrn_reflns_theta_min         1.685
_diffrn_reflns_theta_max         23.254
_diffrn_measured_fraction_theta_max 0.693

_diffrn_reflns_theta_full        17.441
_diffrn_measured_fraction_theta_full 0.725


_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -4
_reflns_limit_h_max              4
_reflns_limit_k_min              0
_reflns_limit_k_max              18
_reflns_limit_l_min              0
_reflns_limit_l_max              15

_oxford_diffrn_Wilson_B_factor   4.25
_oxford_diffrn_Wilson_scale      3.44

_atom_sites_solution_primary     geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.85
_refine_diff_density_max         0.90


# 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     94
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1095
_oxford_refine_ls_R_factor_ref   0.1839
_refine_ls_R_factor_all          0.1839
_refine_ls_wR_factor_ref         0.0626
_refine_ls_wR_factor_all         0.0626
_refine_ls_goodness_of_fit_ref   1.0629
_refine_ls_shift/su_max          0.0001897
_refine_ls_shift/su_mean         0.0000619


# Computed with I/sigma = -10 
_oxford_reflns_number_all        1095
_oxford_refine_ls_R_factor_all   0.1839
_oxford_refine_ls_wR_factor_all  0.0626

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                738
_refine_ls_R_factor_gt           0.1117
_refine_ls_wR_factor_gt          0.0577


_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      sigma
_refine_ls_weighting_details     
;
 Method= 
 SQRT(W) = 1/(Data with the key SIGMA(/FO/) in list 6) 
;

# 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 0.7817(4) 0.59321(9) 0.43128(10) 0.0482 1.0000 Uani D U . . . .
O1 O 0.4916(10) 0.6243(2) 0.0256(3) 0.0652(14) 1.0000 Uiso D U . . . .
O2 O 0.5497(10) 0.6937(2) 0.1348(3) 0.0637(13) 1.0000 Uiso D U . . . .
C1 C 0.8947(12) 0.5821(4) 0.2213(4) 0.0503(14) 1.0000 Uiso D U . . . .
C2 C 1.0860(12) 0.5205(3) 0.2601(4) 0.0488(14) 1.0000 Uiso D U . . . .
C3 C 1.1432(13) 0.4591(3) 0.2123(4) 0.0493(15) 1.0000 Uiso D U . . . .
C4 C 1.0185(13) 0.4541(3) 0.1306(4) 0.0502(14) 1.0000 Uiso D U . . . .
C5 C 0.8441(12) 0.5130(3) 0.0963(4) 0.0530(15) 1.0000 Uiso D U . . . .
C6 C 0.7775(13) 0.5768(4) 0.1401(4) 0.0500(14) 1.0000 Uiso D U . . . .
C7 C 0.9127(13) 0.6535(3) 0.3557(5) 0.0487(14) 1.0000 Uiso D U . . . .
C8 C 1.0722(13) 0.7142(3) 0.3889(4) 0.0479(14) 1.0000 Uiso D U . . . .
C9 C 1.0780(13) 0.7119(3) 0.4764(4) 0.0491(14) 1.0000 Uiso D U . . . .
C10 C 0.9308(9) 0.6497(3) 0.5087(4) 0.0513(14) 1.0000 Uiso D U . . . .
C11 C 0.9077(9) 0.6332(3) 0.5966(4) 0.0578(16) 1.0000 Uiso D U . . . .
C12 C 1.2298(14) 0.7642(4) 0.3367(4) 0.0504(14) 1.0000 Uiso D U . . . .
N1 N 0.8452(10) 0.6418(3) 0.2721(4) 0.0503(13) 1.0000 Uiso D U . . . .
N2 N 1.3646(11) 0.8059(3) 0.2909(4) 0.0546(14) 1.0000 Uiso D U . . . .
N3 N 0.5908(12) 0.6350(3) 0.0975(4) 0.0570(14) 1.0000 Uiso D U . . . .
H1 H 0.726(6) 0.6785(16) 0.2477(19) 0.062(3) 1.0000 Uiso D . . . . .
H2 H 1.1674 0.5234 0.3146 0.0611 1.0000 Uiso R . . . . .
H3 H 1.2714 0.4203 0.2355 0.0630 1.0000 Uiso R . . . . .
H4 H 1.0557 0.4110 0.1011 0.0639 1.0000 Uiso R . . . . .
H5 H 0.7665 0.5107 0.0417 0.0631 1.0000 Uiso R . . . . .
H9 H 1.1788 0.7489 0.5098 0.0621 1.0000 Uiso R . . . . .
H111 H 1.0934 0.6001 0.6130 0.1160 1.0000 Uiso DR . . . . .
H112 H 0.9321 0.6779 0.6277 0.1160 1.0000 Uiso DR . . . . .
H113 H 0.6829 0.6109 0.6066 0.1160 1.0000 Uiso DR . . . . .



_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.523(2)
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 . C7 . 1.727(7) yes
S1 . C10 . 1.702(6) yes
O1 . N3 . 1.229(6) yes
O2 . N3 . 1.237(6) yes
C1 . C2 . 1.460(9) yes
C1 . C6 . 1.379(7) yes
C1 . N1 . 1.377(8) yes
C2 . C3 . 1.380(7) yes
C2 . H2 . 0.927 no
C3 . C4 . 1.393(8) yes
C3 . H3 . 0.926 no
C4 . C5 . 1.364(7) yes
C4 . H4 . 0.931 no
C5 . C6 . 1.386(8) yes
C5 . H5 . 0.924 no
C6 . N3 . 1.432(8) yes
C7 . C8 . 1.357(8) yes
C7 . N1 . 1.387(8) yes
C8 . C9 . 1.420(7) yes
C8 . C12 . 1.389(7) yes
C9 . C10 . 1.368(7) yes
C9 . H9 . 0.936 no
C10 . C11 . 1.463(8) yes
C11 . H112 . 0.956 no
C11 . H113 . 0.958 no
C11 . H111 . 0.953 no
C12 . N2 . 1.185(7) yes
N1 . H1 . 0.89(3) 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
C7 . S1 . C10 . 92.7(3) yes
C2 . C1 . C6 . 119.8(6) yes
C2 . C1 . N1 . 114.7(7) yes
C6 . C1 . N1 . 125.5(5) yes
C1 . C2 . C3 . 117.3(7) yes
C1 . C2 . H2 . 120.7 no
C3 . C2 . H2 . 121.9 no
C2 . C3 . C4 . 122.2(5) yes
C2 . C3 . H3 . 118.3 no
C4 . C3 . H3 . 119.5 no
C3 . C4 . C5 . 118.7(6) yes
C3 . C4 . H4 . 119.4 no
C5 . C4 . H4 . 121.8 no
C4 . C5 . C6 . 122.5(7) yes
C4 . C5 . H5 . 119.2 no
C6 . C5 . H5 . 118.3 no
C5 . C6 . C1 . 119.3(5) yes
C5 . C6 . N3 . 117.5(7) yes
C1 . C6 . N3 . 123.1(6) yes
S1 . C7 . C8 . 111.4(6) yes
S1 . C7 . N1 . 123.3(4) yes
C8 . C7 . N1 . 125.2(6) yes
C7 . C8 . C9 . 111.4(5) yes
C7 . C8 . C12 . 118.8(7) yes
C9 . C8 . C12 . 129.5(6) yes
C8 . C9 . C10 . 114.5(5) yes
C8 . C9 . H9 . 123.4 no
C10 . C9 . H9 . 122.1 no
C9 . C10 . S1 . 110.0(5) yes
C9 . C10 . C11 . 125.4(4) yes
S1 . C10 . C11 . 124.6(2) yes
C10 . C11 . H112 . 109.4 no
C10 . C11 . H113 . 109.4 no
H112 . C11 . H113 . 109.8 no
C10 . C11 . H111 . 109.4 no
H112 . C11 . H111 . 109.3 no
H113 . C11 . H111 . 109.4 no
C8 . C12 . N2 . 178.6(8) yes
C7 . N1 . C1 . 132.9(6) yes
C7 . N1 . H1 . 113(2) no
C1 . N1 . H1 . 114(2) no
C6 . N3 . O2 . 117.8(7) yes
C6 . N3 . O1 . 118.0(5) yes
O2 . N3 . O1 . 124.1(5) yes



# 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
0 2 6 x .
1 5 11 x .
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_chemical_name_common            ROY
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_ROY_ON_1p37GPa
_database_code_depnum_ccdc_archive 'CCDC 2098638'
loop_
_audit_author_name
_audit_author_address
'Nicholas Funnell'
;STFC, ISIS Neutron Facility
United Kingdom
;
_audit_update_record             
;
2021-07-22 deposited with the CCDC.	2021-08-27 downloaded from the CCDC.
;
_audit_creation_date             2021-01-25
_audit_creation_method           'CRYSTALS_ver_14.61_build_7795 '


_chemical_name_systematic        
;
5-methyl-2[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
;


#CheckCIF alerts

_vrf_THETM01_ROY_ON_1p37GPa      
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below.  
;
_vrf_PLAT027_ROY_ON_1p37GPa      
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      17.43 Degree
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below.  
;
_vrf_PLAT029_ROY_ON_1p37GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.729 Why?  
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below.  
;
_vrf_PLAT201_ROY_ON_1p37GPa      
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         17 Report
RESPONSE: The model could only be refined isotropically in order to maintain a 
favourable data-to-parameter ratio, due to numerous unmeasured reflections.
The relatively electron-rich sulfur atom has been modelled anisotropically.
;
_vrf_PLAT340_ROY_ON_1p37GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01091 Ang.  
RESPONSE: These are poor-quality diffraction data.
;
_vrf_PLAT911_ROY_ON_1p37GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.555        417 Report
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below.  
;
_vrf_PLAT082_ROY_ON_1p37GPa      
;
PROBLEM: High R1 Value ..................................       0.12 Report
RESPONSE: These are poor-quality diffraction data and the model has only been 
refined isotropically.
;
_vrf_PLAT910_ROY_ON_1p37GPa      
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).          8 Note  
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below.  
;

_refine_special_details          
; 
In the absence of significant anomalous scattering, Friedel pairs were 
merged. 

Data were collected in a Merrill-Bassett diamond anvil cell, which 
significantly restricts the regions over which reciprocal space can be sampled. 
Thus, these data are poor quality/incomplete, reflected in numerous CheckCIF 
alerts regarding refinement statistics. At all pressures, the atomic 
connectivity is known.

All non-sulfur atoms were refined isotropically; sulfur was refined 
anisotropically. Hydrogen atoms were constrained to ride on their host atoms.

#===============================================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#===============================================================================
Theta sin(th)/Lambda Complete  Expected Measured Total Missing
#-------------------------------------------------------------------------------
 20.82     0.500     0.714         1116      797      319
 23.01     0.550     0.706         1408      994      414
 23.25     0.555     0.706         1446     1021      425
------------------------------------------------------------ ACTA Min. Res. ---

Note: The Reported Completeness refers to the Actual H,K,L Index Range
;

#end of refcif 
_cell_length_a                   3.68945(2)
_cell_length_b                   17.85212(5)
_cell_length_c                   16.13731(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.452(6)
_cell_angle_gamma                90
_cell_volume                     1062.843(7)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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 0.1246 0.1234 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            4

# Given Formula = C12 H9 N3 O2 S1 
# Dc =      1.62 Fooo =    536.00 Mu =      3.01 M =    259.29
# Found Formula = C12 H9 N3 O2 S1 
# Dc =      1.62 FOOO =    536.00 Mu =      3.01 M =    259.29

_chemical_formula_sum            'C12 H9 N3 O2 S1'
_chemical_formula_moiety         'C12 H9 N3 O2 S1'
_chemical_compound_source        'TCI Chemicals'
_chemical_formula_weight         259.29


_cell_measurement_reflns_used    1713
_cell_measurement_theta_min      1.68
_cell_measurement_theta_max      23.18
_cell_measurement_temperature    293

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_max          0.248

_exptl_crystal_density_diffrn    1.620
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.301

# Sheldrick geometric approximatio 0.98 0.99 
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_absorpt_correction_T_min  0.08
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Model from previously-determined structure'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      293
_diffrn_ambient_pressure         1370000
_diffrn_reflns_number            3379
_diffrn_reflns_av_unetI/netI     0.072
_reflns_number_total             1045
_diffrn_reflns_av_R_equivalents  0.079
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1045 
# Theoretical number of reflections is about 3050 


_diffrn_reflns_theta_min         1.701
_diffrn_reflns_theta_max         23.247
_diffrn_measured_fraction_theta_max 0.690

_diffrn_reflns_theta_full        17.435
_diffrn_measured_fraction_theta_full 0.729


_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -4
_reflns_limit_h_max              4
_reflns_limit_k_min              0
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              15

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.93
_refine_diff_density_max         1.09


# 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     94
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1021
_oxford_refine_ls_R_factor_ref   0.1668
_refine_ls_R_factor_all          0.1668
_refine_ls_wR_factor_ref         0.0875
_refine_ls_wR_factor_all         0.0875
_refine_ls_goodness_of_fit_ref   0.9868
_refine_ls_shift/su_max          0.0001072
_refine_ls_shift/su_mean         0.0000328


# Computed with I/sigma = -10 
_oxford_reflns_number_all        1021
_oxford_refine_ls_R_factor_all   0.1668
_oxford_refine_ls_wR_factor_all  0.0875

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                662
_refine_ls_R_factor_gt           0.1187
_refine_ls_wR_factor_gt          0.0796


_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      sigma
_refine_ls_weighting_details     
;
 Method= 
 SQRT(W) = 1/(Data with the key SIGMA(/FO/) in list 6) 
;

# 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 0.7364(5) 0.59154(10) 0.43302(15) 0.0389 1.0000 Uani D U . . . .
O1 O 0.4850(13) 0.6281(3) 0.0245(4) 0.0512(16) 1.0000 Uiso D U . . . .
O2 O 0.5087(13) 0.6960(3) 0.1363(3) 0.0480(15) 1.0000 Uiso D U . . . .
C1 C 0.8678(16) 0.5829(4) 0.2229(6) 0.0366(14) 1.0000 Uiso D U . . . .
C2 C 1.0626(16) 0.5211(4) 0.2570(5) 0.0371(15) 1.0000 Uiso D U . . . .
C3 C 1.1262(15) 0.4589(4) 0.2112(5) 0.0360(16) 1.0000 Uiso D U . . . .
C4 C 1.0098(17) 0.4564(4) 0.1281(5) 0.0394(16) 1.0000 Uiso D U . . . .
C5 C 0.8329(16) 0.5151(4) 0.0926(5) 0.0385(15) 1.0000 Uiso D U . . . .
C6 C 0.7647(17) 0.5774(4) 0.1418(5) 0.0385(14) 1.0000 Uiso D U . . . .
C7 C 0.8688(16) 0.6528(4) 0.3577(5) 0.0365(15) 1.0000 Uiso D U . . . .
C8 C 1.0304(18) 0.7152(4) 0.3907(6) 0.0379(15) 1.0000 Uiso D U . . . .
C9 C 1.0424(17) 0.7144(4) 0.4776(6) 0.0394(16) 1.0000 Uiso D U . . . .
C10 C 0.8885(13) 0.6492(3) 0.5111(6) 0.0386(15) 1.0000 Uiso D U . . . .
C11 C 0.8593(13) 0.6268(3) 0.6000(5) 0.0473(18) 1.0000 Uiso D U . . . .
C12 C 1.2002(17) 0.7678(4) 0.3399(5) 0.0374(15) 1.0000 Uiso D U . . . .
N1 N 0.8081(13) 0.6428(3) 0.2722(4) 0.0355(14) 1.0000 Uiso D U . . . .
N2 N 1.3372(15) 0.8063(4) 0.2919(4) 0.0428(16) 1.0000 Uiso D U . . . .
N3 N 0.5795(15) 0.6366(3) 0.0983(5) 0.0443(15) 1.0000 Uiso D U . . . .
H1 H 0.703(5) 0.6784(16) 0.2462(18) 0.042(3) 1.0000 Uiso D . . . . .
H2 H 1.1438 0.5235 0.3111 0.0459 1.0000 Uiso R . . . . .
H3 H 1.2452 0.4195 0.2342 0.0434 1.0000 Uiso R . . . . .
H4 H 1.0535 0.4137 0.0972 0.0475 1.0000 Uiso R . . . . .
H5 H 0.7617 0.5126 0.0383 0.0464 1.0000 Uiso R . . . . .
H9 H 1.1385 0.7524 0.5090 0.0470 1.0000 Uiso R . . . . .
H111 H 1.0746 0.5998 0.6166 0.0713 1.0000 Uiso DR . . . . .
H112 H 0.8313 0.6710 0.6340 0.0698 1.0000 Uiso DR . . . . .
H113 H 0.6558 0.5947 0.6068 0.0711 1.0000 Uiso DR . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.4499(18)
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 . C7 . 1.709(8) yes
S1 . C10 . 1.718(7) yes
O1 . N3 . 1.247(8) yes
O2 . N3 . 1.254(8) yes
C1 . C2 . 1.424(9) yes
C1 . C6 . 1.364(10) yes
C1 . N1 . 1.352(9) yes
C2 . C3 . 1.356(10) yes
C2 . H2 . 0.922 no
C3 . C4 . 1.405(9) yes
C3 . H3 . 0.907 no
C4 . C5 . 1.359(10) yes
C4 . H4 . 0.926 no
C5 . C6 . 1.390(10) yes
C5 . H5 . 0.914 no
C6 . N3 . 1.438(9) yes
C7 . C8 . 1.369(10) yes
C7 . N1 . 1.407(8) yes
C8 . C9 . 1.403(11) yes
C8 . C12 . 1.398(10) yes
C9 . C10 . 1.405(9) yes
C9 . H9 . 0.915 no
C10 . C11 . 1.495(11) yes
C11 . H111 . 0.965 no
C11 . H112 . 0.967 no
C11 . H113 . 0.951 no
C12 . N2 . 1.156(9) yes
N1 . H1 . 0.85(3) 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
C7 . S1 . C10 . 92.5(4) yes
C2 . C1 . C6 . 116.8(6) yes
C2 . C1 . N1 . 118.0(8) yes
C6 . C1 . N1 . 125.2(7) yes
C1 . C2 . C3 . 120.9(8) yes
C1 . C2 . H2 . 119.3 no
C3 . C2 . H2 . 119.8 no
C2 . C3 . C4 . 119.6(7) yes
C2 . C3 . H3 . 119.8 no
C4 . C3 . H3 . 120.7 no
C3 . C4 . C5 . 121.3(7) yes
C3 . C4 . H4 . 119.2 no
C5 . C4 . H4 . 119.5 no
C4 . C5 . C6 . 117.7(8) yes
C4 . C5 . H5 . 120.0 no
C6 . C5 . H5 . 122.3 no
C5 . C6 . C1 . 123.7(7) yes
C5 . C6 . N3 . 113.3(8) yes
C1 . C6 . N3 . 122.9(6) yes
S1 . C7 . C8 . 111.7(7) yes
S1 . C7 . N1 . 124.9(5) yes
C8 . C7 . N1 . 123.4(7) yes
C7 . C8 . C9 . 113.1(7) yes
C7 . C8 . C12 . 120.9(8) yes
C9 . C8 . C12 . 125.6(6) yes
C8 . C9 . C10 . 112.5(6) yes
C8 . C9 . H9 . 123.6 no
C10 . C9 . H9 . 123.9 no
C9 . C10 . S1 . 110.3(6) yes
C9 . C10 . C11 . 128.5(5) yes
S1 . C10 . C11 . 121.2(3) yes
C10 . C11 . H111 . 109.6 no
C10 . C11 . H112 . 109.5 no
H111 . C11 . H112 . 110.0 no
C10 . C11 . H113 . 109.5 no
H111 . C11 . H113 . 108.4 no
H112 . C11 . H113 . 109.8 no
C8 . C12 . N2 . 173.4(10) yes
C7 . N1 . C1 . 130.7(6) yes
C7 . N1 . H1 . 117(2) no
C1 . N1 . H1 . 112(2) no
C6 . N3 . O2 . 118.9(8) yes
C6 . N3 . O1 . 120.3(6) yes
O2 . N3 . O1 . 120.8(7) yes



# 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 1 6 x .
-1 6 13 x .
-1 3 9 x .
1 3 9 x .
0 1 4 x .
3 0 4 x .
1 8 1 x .
-2 10 2 x .
-1 4 11 x .
-2 12 3 x .
2 0 6 x .
0 13 4 x .
-2 14 5 x .
0 14 5 x .
0 6 13 x .
2 6 12 x .
0 8 14 x .
-3 3 10 x .
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_chemical_name_common            ROY
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_ROY_ON_1p91GPa
_database_code_depnum_ccdc_archive 'CCDC 2098639'
loop_
_audit_author_name
_audit_author_address
'Nicholas Funnell'
;STFC, ISIS Neutron Facility
United Kingdom
;
_audit_update_record             
;
2021-07-22 deposited with the CCDC.	2021-08-27 downloaded from the CCDC.
;
_audit_creation_date             2021-01-26
_audit_creation_method           'CRYSTALS_ver_14.61_build_7795 '


_chemical_name_systematic        
;
5-methyl-2[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
;


#CheckCIF alerts
_vrf_THETM01_ROY_ON_1p91GPa      
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below.  
;
_vrf_PLAT027_ROY_ON_1p91GPa      
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      17.42 Degree
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below.  
;
_vrf_PLAT029_ROY_ON_1p91GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.730 Why?  
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below. 
;
_vrf_PLAT201_ROY_ON_1p91GPa      
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         17 Report
RESPONSE: The model could only be refined isotropically in order to maintain a 
favourable data-to-parameter ratio, due to numerous unmeasured reflections.
The relatively electron-rich sulfur atom has been modelled anisotropically.
;
_vrf_PLAT340_ROY_ON_1p91GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01027 Ang.  
RESPONSE: These are poor-quality diffraction data.
;
_vrf_PLAT911_ROY_ON_1p91GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.555        403 Report
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below. 
;
_vrf_PLAT157_ROY_ON_1p91GPa      
;
PROBLEM: Non-standard Monoclinic Beta Angle less 90 Deg        89.65 Degree
RESPONSE: This is a series of high pressure structures where the beta angle
decreases, passing through 90 degrees. The non-standard beta angle allows the
change in angle to be followed clearly.
;
_vrf_PLAT411_ROY_ON_1p91GPa      
;
PROBLEM: Short Inter H...H Contact  H5       ..H5       .       2.13 Ang.  
RESPONSE: These are high-pressure data - short contacts are expected.
;
_vrf_PLAT413_ROY_ON_1p91GPa      
;
PROBLEM: Short Inter XH3 .. XHn     H111     ..H113     .       2.11 Ang.  
RESPONSE: These are high-pressure data - short contacts are expected.
;
_vrf_PLAT910_ROY_ON_1p91GPa      
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).          8 Note  
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below.  
;
# end Validation Reply Form



_refine_special_details          
; 
In the absence of significant anomalous scattering, Friedel pairs were 
merged. 

Data were collected in a Merrill-Bassett diamond anvil cell, which 
significantly restricts the regions over which reciprocal space can be sampled. 
Thus, these data are poor quality/incomplete, reflected in numerous CheckCIF 
alerts regarding refinement statistics. At all pressures, the atomic 
connectivity is known.

All non-sulfur atoms were refined isotropically; sulfur was refined 
anisotropically. Hydrogen atoms were constrained to ride on their host atoms.


#===============================================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#===============================================================================
Theta sin(th)/Lambda Complete  Expected Measured Total Missing
#-------------------------------------------------------------------------------
 20.82     0.500     0.714         1078      770      308
 23.01     0.550     0.705         1359      958      401
 23.22     0.555     0.705         1395      984      411
------------------------------------------------------------ ACTA Min. Res. ---

Note: The Reported Completeness refers to the Actual H,K,L Index Range
;


#end of refcif 
_cell_length_a                   3.631200(17)
_cell_length_b                   17.68860(4)
_cell_length_c                   16.02610(5)
_cell_angle_alpha                90
_cell_angle_beta                 89.648(5)
_cell_angle_gamma                90
_cell_volume                     1029.350(6)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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 0.1246 0.1234 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            4

# Given Formula = C12 H9 N3 O2 S1 
# Dc =      1.67 Fooo =    536.00 Mu =      3.11 M =    259.29
# Found Formula = C12 H9 N3 O2 S1 
# Dc =      1.67 FOOO =    536.00 Mu =      3.11 M =    259.29

_chemical_formula_sum            'C12 H9 N3 O2 S1'
_chemical_formula_moiety         'C12 H9 N3 O2 S1'
_chemical_compound_source        'TCI Chemicals'
_chemical_formula_weight         259.29


_cell_measurement_reflns_used    1893
_cell_measurement_theta_min      1.70
_cell_measurement_theta_max      23.17
_cell_measurement_temperature    293

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_max          0.248

_exptl_crystal_density_diffrn    1.673
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.311

# Sheldrick geometric approximatio 0.98 0.98 
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_absorpt_correction_T_min  0.15
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Model from previously-determined structure'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      293
_diffrn_ambient_pressure         1910000
_diffrn_reflns_number            3093
_diffrn_reflns_av_unetI/netI     0.037
_reflns_number_total             1005
_diffrn_reflns_av_R_equivalents  0.042
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1005 
# Theoretical number of reflections is about 2945 


_diffrn_reflns_theta_min         1.715
_diffrn_reflns_theta_max         23.221
_diffrn_measured_fraction_theta_max 0.691

_diffrn_reflns_theta_full        17.416
_diffrn_measured_fraction_theta_full 0.730


_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -4
_reflns_limit_h_max              4
_reflns_limit_k_min              0
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              15

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.86
_refine_diff_density_max         0.80


# 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     94
_refine_ls_number_parameters     82
_refine_ls_number_reflns         984
_oxford_refine_ls_R_factor_ref   0.1401
_refine_ls_R_factor_all          0.1401
_refine_ls_wR_factor_ref         0.0407
_refine_ls_wR_factor_all         0.0407
_refine_ls_goodness_of_fit_ref   1.0777
_refine_ls_shift/su_max          0.0001395
_refine_ls_shift/su_mean         0.0000293


# Computed with I/sigma = -10 
_oxford_reflns_number_all        984
_oxford_refine_ls_R_factor_all   0.1401
_oxford_refine_ls_wR_factor_all  0.0407

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                780
_refine_ls_R_factor_gt           0.1038
_refine_ls_wR_factor_gt          0.0384


_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      sigma
_refine_ls_weighting_details     
;
 Method= 
 SQRT(W) = 1/(Data with the key SIGMA(/FO/) in list 6) 
;

# 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 0.7043(4) 0.58954(11) 0.43423(11) 0.0317 1.0000 Uani D U . . . .
O1 O 0.4713(12) 0.6315(3) 0.0238(4) 0.0460(15) 1.0000 Uiso D U . . . .
O2 O 0.4882(11) 0.6991(3) 0.1378(4) 0.0455(16) 1.0000 Uiso D U . . . .
C1 C 0.8544(15) 0.5839(4) 0.2229(5) 0.0313(15) 1.0000 Uiso D U . . . .
C2 C 1.0392(16) 0.5208(4) 0.2575(6) 0.0318(17) 1.0000 Uiso D U . . . .
C3 C 1.1135(15) 0.4603(4) 0.2083(5) 0.0313(17) 1.0000 Uiso D U . . . .
C4 C 1.0057(14) 0.4563(4) 0.1258(5) 0.0337(18) 1.0000 Uiso D U . . . .
C5 C 0.8249(16) 0.5171(4) 0.0888(5) 0.0287(16) 1.0000 Uiso D U . . . .
C6 C 0.7521(15) 0.5792(4) 0.1407(5) 0.0306(15) 1.0000 Uiso D U . . . .
C7 C 0.8421(16) 0.6528(4) 0.3591(5) 0.0312(17) 1.0000 Uiso D U . . . .
C8 C 1.0032(14) 0.7148(4) 0.3938(5) 0.0295(17) 1.0000 Uiso D U . . . .
C9 C 1.0080(15) 0.7125(4) 0.4817(5) 0.0318(18) 1.0000 Uiso D U . . . .
C10 C 0.8529(11) 0.6492(3) 0.5136(5) 0.0320(16) 1.0000 Uiso D U . . . .
C11 C 0.8098(11) 0.6230(3) 0.6024(4) 0.0378(19) 1.0000 Uiso D U . . . .
C12 C 1.1802(15) 0.7691(5) 0.3418(4) 0.0314(16) 1.0000 Uiso D U . . . .
N1 N 0.7825(14) 0.6435(4) 0.2737(4) 0.0323(16) 1.0000 Uiso D U . . . .
N2 N 1.3230(14) 0.8064(3) 0.2942(4) 0.0370(16) 1.0000 Uiso D U . . . .
N3 N 0.5598(14) 0.6404(4) 0.0965(5) 0.0402(16) 1.0000 Uiso D U . . . .
H1 H 0.658(8) 0.678(2) 0.251(3) 0.040(5) 1.0000 Uiso D . . . . .
H2 H 1.1096 0.5206 0.3129 0.0401 1.0000 Uiso R . . . . .
H3 H 1.2429 0.4196 0.2305 0.0409 1.0000 Uiso R . . . . .
H4 H 1.0540 0.4131 0.0943 0.0410 1.0000 Uiso R . . . . .
H5 H 0.7562 0.5160 0.0330 0.0421 1.0000 Uiso R . . . . .
H9 H 1.1091 0.7504 0.5146 0.0420 1.0000 Uiso R . . . . .
H111 H 0.9919 0.5851 0.6138 0.0581 1.0000 Uiso DR . . . . .
H112 H 0.8418 0.6655 0.6392 0.0581 1.0000 Uiso DR . . . . .
H113 H 0.5680 0.6023 0.6100 0.0580 1.0000 Uiso DR . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.554(2)
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 . C7 . 1.715(8) yes
S1 . C10 . 1.741(7) yes
O1 . N3 . 1.221(7) yes
O2 . N3 . 1.258(8) yes
C1 . C2 . 1.417(10) yes
C1 . C6 . 1.373(9) yes
C1 . N1 . 1.358(9) yes
C2 . C3 . 1.356(9) yes
C2 . H2 . 0.926 no
C3 . C4 . 1.382(9) yes
C3 . H3 . 0.932 no
C4 . C5 . 1.394(9) yes
C4 . H4 . 0.932 no
C5 . C6 . 1.403(10) yes
C5 . H5 . 0.929 no
C6 . N3 . 1.472(10) yes
C7 . C8 . 1.364(9) yes
C7 . N1 . 1.397(9) yes
C8 . C9 . 1.410(9) yes
C8 . C12 . 1.423(9) yes
C9 . C10 . 1.353(8) yes
C9 . H9 . 0.930 no
C10 . C11 . 1.504(9) yes
C11 . H111 . 0.960 no
C11 . H112 . 0.962 no
C11 . H113 . 0.958 no
C12 . N2 . 1.132(7) yes
N1 . H1 . 0.84(4) 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
C7 . S1 . C10 . 91.6(4) yes
C2 . C1 . C6 . 117.4(6) yes
C2 . C1 . N1 . 117.8(8) yes
C6 . C1 . N1 . 124.8(7) yes
C1 . C2 . C3 . 119.1(9) yes
C1 . C2 . H2 . 120.9 no
C3 . C2 . H2 . 120.0 no
C2 . C3 . C4 . 122.7(7) yes
C2 . C3 . H3 . 119.0 no
C4 . C3 . H3 . 118.3 no
C3 . C4 . C5 . 120.4(8) yes
C3 . C4 . H4 . 120.3 no
C5 . C4 . H4 . 119.3 no
C4 . C5 . C6 . 116.0(8) yes
C4 . C5 . H5 . 121.6 no
C6 . C5 . H5 . 122.4 no
C5 . C6 . C1 . 124.4(7) yes
C5 . C6 . N3 . 112.3(8) yes
C1 . C6 . N3 . 123.3(7) yes
S1 . C7 . C8 . 111.3(7) yes
S1 . C7 . N1 . 124.4(5) yes
C8 . C7 . N1 . 124.3(6) yes
C7 . C8 . C9 . 113.1(6) yes
C7 . C8 . C12 . 119.8(8) yes
C9 . C8 . C12 . 126.7(6) yes
C8 . C9 . C10 . 113.2(6) yes
C8 . C9 . H9 . 123.6 no
C10 . C9 . H9 . 123.3 no
S1 . C10 . C9 . 110.9(6) yes
S1 . C10 . C11 . 118.3(3) yes
C9 . C10 . C11 . 130.8(4) yes
C10 . C11 . H111 . 109.1 no
C10 . C11 . H112 . 109.1 no
H111 . C11 . H112 . 110.0 no
C10 . C11 . H113 . 109.1 no
H111 . C11 . H113 . 109.9 no
H112 . C11 . H113 . 109.6 no
C8 . C12 . N2 . 172.7(10) yes
C7 . N1 . C1 . 130.5(7) yes
C7 . N1 . H1 . 115(3) no
C1 . N1 . H1 . 114(3) no
C6 . N3 . O2 . 116.8(7) yes
C6 . N3 . O1 . 119.5(7) yes
O2 . N3 . O1 . 123.7(7) yes



# 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 5 11 x .
-1 6 13 x .
1 3 9 x .
-2 12 3 x .
1 13 4 x .
-2 14 5 x .
3 10 0 x .
3 7 1 x .
0 13 4 x .
-1 3 9 x .
2 0 6 x .
2 10 1 x .
0 14 5 x .
-3 3 10 x .
3 8 0 x .
1 11 2 x .
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_chemical_name_common            ROY
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_ROY_ON_decompress_0p0GPa
_database_code_depnum_ccdc_archive 'CCDC 2098644'
loop_
_audit_author_name
_audit_author_address
'Nicholas Funnell'
;STFC, ISIS Neutron Facility
United Kingdom
;
_audit_update_record             
;
2021-07-22 deposited with the CCDC.	2021-08-27 downloaded from the CCDC.
;
_audit_creation_date             2021-01-26
_audit_creation_method           'CRYSTALS_ver_14.61_build_7795 '


_chemical_name_systematic        
;
5-methyl-2[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
;


#CheckCIF alerts
_vrf_THETM01_ROY_ON_decompress_0p0GPa 
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below.  
;
_vrf_PLAT027_ROY_ON_decompress_0p0GPa 
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      17.44 Degree
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below. 
;
_vrf_PLAT029_ROY_ON_decompress_0p0GPa 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.718 Why?  
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below. 
;
_vrf_PLAT201_ROY_ON_decompress_0p0GPa 
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         17 Report
RESPONSE: The model could only be refined isotropically in order to maintain a 
favourable data-to-parameter ratio, due to numerous unmeasured reflections.
The relatively electron-rich sulfur atom has been modelled anisotropically.
;
_vrf_PLAT911_ROY_ON_decompress_0p0GPa 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.555        435 Report
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below.  
;
_vrf_PLAT082_ROY_ON_decompress_0p0GPa 
;
PROBLEM: High R1 Value ..................................       0.13 Report
RESPONSE: These are poor-quality diffraction data and the model has only been 
refined isotropically.
;
_vrf_PLAT340_ROY_ON_decompress_0p0GPa 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00745 Ang.  
RESPONSE: These are poor-quality diffraction data.
;
_vrf_PLAT910_ROY_ON_decompress_0p0GPa 
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).          8 Note  
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below.  
;


_refine_special_details          
; 
In the absence of significant anomalous scattering, Friedel pairs were 
merged. 

Data were collected in a Merrill-Bassett diamond anvil cell, which 
significantly restricts the regions over which reciprocal space can be sampled. 
Thus, these data are poor quality/incomplete, reflected in numerous CheckCIF 
alerts regarding refinement statistics. At all pressures, the atomic 
connectivity is known.

All non-sulfur atoms were refined isotropically; sulfur was refined 
anisotropically. Hydrogen atoms were constrained to ride on their host atoms.


#===============================================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#===============================================================================
Theta sin(th)/Lambda Complete  Expected Measured Total Missing
#-------------------------------------------------------------------------------
 20.82     0.500     0.723         1223      884      339
 23.01     0.550     0.729         1589     1158      431
 23.25     0.555     0.728         1631     1188      443
------------------------------------------------------------ ACTA Min. Res. ---

Note: The Reported Completeness refers to the Actual H,K,L Index Range
;


#end of refcif 
_cell_length_a                   3.94747(2)
_cell_length_b                   18.67316(6)
_cell_length_c                   16.33187(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.736(7)
_cell_angle_gamma                90
_cell_volume                     1201.293(13)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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 0.1246 0.1234 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            4

# Given Formula = C12 H9 N3 O2 S1 
# Dc =      1.43 Fooo =    536.00 Mu =      2.66 M =    259.29
# Found Formula = C12 H9 N3 O2 S1 
# Dc =      1.43 FOOO =    536.00 Mu =      2.66 M =    259.29

_chemical_formula_sum            'C12 H9 N3 O2 S1'
_chemical_formula_moiety         'C12 H9 N3 O2 S1'
_chemical_compound_source        'TCI Chemicals'
_chemical_formula_weight         259.29


_cell_measurement_reflns_used    1804
_cell_measurement_theta_min      1.65
_cell_measurement_theta_max      23.14
_cell_measurement_temperature    293

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_max          0.248

_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             536
_exptl_absorpt_coefficient_mu    0.266

# Sheldrick geometric approximatio 0.98 0.99 
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_absorpt_correction_T_min  0.13
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Model from previously-determined structure'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      293
_diffrn_reflns_number            4298
_diffrn_reflns_av_unetI/netI     0.055
_reflns_number_total             1204
_diffrn_reflns_av_R_equivalents  0.048
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1204 
# Theoretical number of reflections is about 3450 


_diffrn_reflns_theta_min         1.658
_diffrn_reflns_theta_max         23.253
_diffrn_measured_fraction_theta_max 0.692

_diffrn_reflns_theta_full        17.440
_diffrn_measured_fraction_theta_full 0.718


_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -4
_reflns_limit_h_max              4
_reflns_limit_k_min              0
_reflns_limit_k_max              19
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.77
_refine_diff_density_max         0.80


# 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     94
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1188
_oxford_refine_ls_R_factor_ref   0.1854
_refine_ls_R_factor_all          0.1854
_refine_ls_wR_factor_ref         0.0358
_refine_ls_wR_factor_all         0.0358
_refine_ls_goodness_of_fit_ref   0.9591
_refine_ls_shift/su_max          0.0002518
_refine_ls_shift/su_mean         0.0000792


# Computed with I/sigma = -10 
_oxford_reflns_number_all        1188
_oxford_refine_ls_R_factor_all   0.1854
_oxford_refine_ls_wR_factor_all  0.0358

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                728
_refine_ls_R_factor_gt           0.1251
_refine_ls_wR_factor_gt          0.0325


_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      sigma
_refine_ls_weighting_details     
;
 Method= 
 SQRT(W) = 1/(Data with the key SIGMA(/FO/) in list 6) 
;

# 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 0.8550(3) 0.59821(6) 0.42899(10) 0.0656 1.0000 Uani D U . . . .
O1 O 0.5066(7) 0.61641(16) 0.0305(3) 0.0870(11) 1.0000 Uiso D U . . . .
O2 O 0.5984(8) 0.68595(18) 0.1339(3) 0.0868(11) 1.0000 Uiso D U . . . .
N1 N 0.9020(8) 0.64175(18) 0.2711(3) 0.0653(11) 1.0000 Uiso D U . . . .
N2 N 1.4095(8) 0.80205(17) 0.2880(3) 0.0685(12) 1.0000 Uiso D U . . . .
N3 N 0.6319(9) 0.6270(2) 0.0993(3) 0.0812(11) 1.0000 Uiso D U . . . .
C1 C 0.9439(10) 0.5811(2) 0.2229(4) 0.0671(12) 1.0000 Uiso D U . . . .
C2 C 1.1253(10) 0.5222(2) 0.2633(4) 0.0675(12) 1.0000 Uiso D U . . . .
C3 C 1.1659(9) 0.4618(2) 0.2179(4) 0.0676(12) 1.0000 Uiso D U . . . .
C4 C 1.0367(9) 0.4564(3) 0.1391(4) 0.0701(12) 1.0000 Uiso D U . . . .
C5 C 0.8605(9) 0.5102(2) 0.0995(3) 0.0692(12) 1.0000 Uiso D U . . . .
C6 C 0.8164(9) 0.5728(3) 0.1448(4) 0.0703(11) 1.0000 Uiso D U . . . .
C7 C 0.9744(10) 0.6541(2) 0.3524(4) 0.0616(10) 1.0000 Uiso D U . . . .
C8 C 1.1334(10) 0.7136(2) 0.3844(4) 0.0625(11) 1.0000 Uiso D U . . . .
C9 C 1.1583(9) 0.7134(2) 0.4687(4) 0.0666(12) 1.0000 Uiso D U . . . .
C10 C 1.0187(7) 0.65517(18) 0.5029(4) 0.0692(10) 1.0000 Uiso D U . . . .
C11 C 0.9858(7) 0.63794(18) 0.5920(4) 0.0766(13) 1.0000 Uiso D U . . . .
C12 C 1.2782(10) 0.7656(3) 0.3340(4) 0.0629(11) 1.0000 Uiso D U . . . .
H1 H 0.782(4) 0.6744(11) 0.2469(13) 0.067(3) 1.0000 Uiso D . . . . .
H2 H 1.2104 0.5258 0.3172 0.0790 1.0000 Uiso R . . . . .
H3 H 1.2913 0.4238 0.2421 0.0779 1.0000 Uiso R . . . . .
H4 H 1.0651 0.4137 0.1115 0.0868 1.0000 Uiso R . . . . .
H5 H 0.7716 0.5060 0.0465 0.0750 1.0000 Uiso R . . . . .
H9 H 1.2601 0.7510 0.4992 0.0860 1.0000 Uiso R . . . . .
H111 H 1.1646 0.6056 0.6109 0.1259 1.0000 Uiso DR . . . . .
H112 H 1.0019 0.6811 0.6237 0.1261 1.0000 Uiso DR . . . . .
H113 H 0.7706 0.6156 0.5987 0.1261 1.0000 Uiso DR . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.4233(10)
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 . C7 . 1.719(6) yes
S1 . C10 . 1.704(5) yes
O1 . N3 . 1.215(6) yes
O2 . N3 . 1.247(4) yes
N1 . C1 . 1.395(6) yes
N1 . C7 . 1.359(6) yes
N1 . H1 . 0.85(2) no
N2 . C12 . 1.160(6) yes
N3 . C6 . 1.428(6) yes
C1 . C2 . 1.447(7) yes
C1 . C6 . 1.349(7) yes
C2 . C3 . 1.364(6) yes
C2 . H2 . 0.924 no
C3 . C4 . 1.356(8) yes
C3 . H3 . 0.938 no
C4 . C5 . 1.361(5) yes
C4 . H4 . 0.928 no
C5 . C6 . 1.399(5) yes
C5 . H5 . 0.917 no
C7 . C8 . 1.363(6) yes
C8 . C9 . 1.375(7) yes
C8 . C12 . 1.418(6) yes
C9 . C10 . 1.356(5) yes
C9 . H9 . 0.936 no
C10 . C11 . 1.504(7) yes
C11 . H111 . 0.965 no
C11 . H112 . 0.959 no
C11 . H113 . 0.959 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
C7 . S1 . C10 . 91.6(3) yes
C1 . N1 . C7 . 131.6(4) yes
C1 . N1 . H1 . 113.7(16) no
C7 . N1 . H1 . 113.9(16) no
O2 . N3 . O1 . 120.9(4) yes
O2 . N3 . C6 . 117.1(5) yes
O1 . N3 . C6 . 121.9(5) yes
N1 . C1 . C2 . 115.7(6) yes
N1 . C1 . C6 . 125.2(5) yes
C2 . C1 . C6 . 119.1(5) yes
C1 . C2 . C3 . 116.9(6) yes
C1 . C2 . H2 . 121.0 no
C3 . C2 . H2 . 122.0 no
C2 . C3 . C4 . 121.8(5) yes
C2 . C3 . H3 . 118.3 no
C4 . C3 . H3 . 120.0 no
C3 . C4 . C5 . 123.0(5) yes
C3 . C4 . H4 . 118.4 no
C5 . C4 . H4 . 118.6 no
C4 . C5 . C6 . 116.2(6) yes
C4 . C5 . H5 . 122.5 no
C6 . C5 . H5 . 121.3 no
N3 . C6 . C5 . 113.2(6) yes
N3 . C6 . C1 . 123.8(5) yes
C5 . C6 . C1 . 123.0(5) yes
S1 . C7 . N1 . 123.9(3) yes
S1 . C7 . C8 . 110.9(5) yes
N1 . C7 . C8 . 125.1(4) yes
C7 . C8 . C9 . 112.6(4) yes
C7 . C8 . C12 . 121.9(6) yes
C9 . C8 . C12 . 125.3(5) yes
C8 . C9 . C10 . 114.2(5) yes
C8 . C9 . H9 . 122.1 no
C10 . C9 . H9 . 123.7 no
S1 . C10 . C9 . 110.8(5) yes
S1 . C10 . C11 . 119.9(2) yes
C9 . C10 . C11 . 129.3(4) yes
C10 . C11 . H111 . 109.7 no
C10 . C11 . H112 . 109.7 no
H111 . C11 . H112 . 109.4 no
C10 . C11 . H113 . 109.7 no
H111 . C11 . H113 . 109.0 no
H112 . C11 . H113 . 109.4 no
C8 . C12 . N2 . 172.6(6) yes



# 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 6 x .
1 7 11 x .
-1 0 4 x .
-2 12 1 x .
3 10 0 x .
-1 15 3 x .
-2 13 2 x .
1 3 7 x .
0 8 12 x .
0 7 11 x .
0 5 9 x .
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_chemical_name_common            ROY
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_ROY_ON_4p18GPa
_database_code_depnum_ccdc_archive 'CCDC 2098643'
loop_
_audit_author_name
_audit_author_address
'Nicholas Funnell'
;STFC, ISIS Neutron Facility
United Kingdom
;
_audit_update_record             
;
2021-07-22 deposited with the CCDC.	2021-08-27 downloaded from the CCDC.
;
_audit_creation_date             2021-01-26
_audit_creation_method           'CRYSTALS_ver_14.61_build_7795 '


_chemical_name_systematic        
;
5-methyl-2[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
;


#CheckCIF alerts
_vrf_THETM01_ROY_ON_4p18GPa      
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below.  
;
_vrf_PLAT027_ROY_ON_4p18GPa      
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      17.44 Degree
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below.  
;
_vrf_PLAT029_ROY_ON_4p18GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.698 Why?  
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below.  
;
_vrf_PLAT201_ROY_ON_4p18GPa      
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         17 Report
RESPONSE: The model could only be refined isotropically in order to maintain a 
favourable data-to-parameter ratio, due to numerous unmeasured reflections.
The relatively electron-rich sulfur atom has been modelled anisotropically.
;
_vrf_PLAT340_ROY_ON_4p18GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01109 Ang.  
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below.  
;
_vrf_PLAT413_ROY_ON_4p18GPa      
;
PROBLEM: Short Inter XH3 .. XHn     H2       ..H111     .       1.93 Ang.  
RESPONSE: These are high-pressure data - short contacts are expected.
;
_vrf_PLAT911_ROY_ON_4p18GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.555        397 Report
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below. 
;
_vrf_PLAT157_ROY_ON_4p18GPa      
;
PROBLEM: Non-standard Monoclinic Beta Angle less 90 Deg        88.04 Degree
RESPONSE: This is a series of high pressure structures where the beta angle
decreases, passing through 90 degrees. The non-standard beta angle allows the
change in angle to be followed clearly.
;
_vrf_PLAT411_ROY_ON_4p18GPa      
;
PROBLEM: Short Inter H...H Contact  H5       ..H5       .       2.11 Ang.  
RESPONSE: These are high-pressure data - short contacts are expected.
;
_vrf_PLAT910_ROY_ON_4p18GPa      
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).          8 Note  
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below.  
;


_refine_special_details          
; 
In the absence of significant anomalous scattering, Friedel pairs were 
merged. 

Data were collected in a Merrill-Bassett diamond anvil cell, which 
significantly restricts the regions over which reciprocal space can be sampled. 
Thus, these data are poor quality/incomplete, reflected in numerous CheckCIF 
alerts regarding refinement statistics. At all pressures, the atomic 
connectivity is known.

All non-sulfur atoms were refined isotropically; sulfur was refined 
anisotropically. Hydrogen atoms were constrained to ride on their host atoms.


#===============================================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#===============================================================================
Theta sin(th)/Lambda Complete  Expected Measured Total Missing
#-------------------------------------------------------------------------------
 20.82     0.500     0.696          999      695      304
 23.01     0.550     0.688         1263      869      394
 23.25     0.555     0.685         1285      880      405
------------------------------------------------------------ ACTA Min. Res. ---

Note: The Reported Completeness refers to the Actual H,K,L Index Range
;


#end of refcif 
_cell_length_a                   3.49690(2)
_cell_length_b                   17.29910(6)
_cell_length_c                   15.77880(6)
_cell_angle_alpha                90
_cell_angle_beta                 88.037(7)
_cell_angle_gamma                90
_cell_volume                     953.950(8)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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 0.1246 0.1234 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            4

# Given Formula = C12 H9 N3 O2 S1 
# Dc =      1.81 Fooo =    536.00 Mu =      3.35 M =    259.29
# Found Formula = C12 H9 N3 O2 S1 
# Dc =      1.81 FOOO =    536.00 Mu =      3.35 M =    259.29

_chemical_formula_sum            'C12 H9 N3 O2 S1'
_chemical_formula_moiety         'C12 H9 N3 O2 S1'
_chemical_compound_source        'TCI Chemicals'
_chemical_formula_weight         259.29


_cell_measurement_reflns_used    1540
_cell_measurement_theta_min      1.74
_cell_measurement_theta_max      23.14
_cell_measurement_temperature    293

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_max          0.248

_exptl_crystal_density_diffrn    1.805
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.335

# Sheldrick geometric approximatio 0.98 0.98 
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_absorpt_correction_T_min  0.09
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Model from previously-determined structure'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      293
_diffrn_ambient_pressure         4180000
_diffrn_reflns_number            2440
_diffrn_reflns_av_unetI/netI     0.055
_reflns_number_total             889
_diffrn_reflns_av_R_equivalents  0.048
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 889 
# Theoretical number of reflections is about 2739 


_diffrn_reflns_theta_min         1.747
_diffrn_reflns_theta_max         23.251
_diffrn_measured_fraction_theta_max 0.655

_diffrn_reflns_theta_full        17.438
_diffrn_measured_fraction_theta_full 0.698


_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -3
_reflns_limit_h_max              3
_reflns_limit_k_min              0
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.91
_refine_diff_density_max         0.82


# 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     94
_refine_ls_number_parameters     82
_refine_ls_number_reflns         880
_oxford_refine_ls_R_factor_ref   0.1211
_refine_ls_R_factor_all          0.1211
_refine_ls_wR_factor_ref         0.0617
_refine_ls_wR_factor_all         0.0617
_refine_ls_goodness_of_fit_ref   1.1493
_refine_ls_shift/su_max          0.0001238
_refine_ls_shift/su_mean         0.0000332


# Computed with I/sigma = -10 
_oxford_reflns_number_all        880
_oxford_refine_ls_R_factor_all   0.1211
_oxford_refine_ls_wR_factor_all  0.0617

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                651
_refine_ls_R_factor_gt           0.0799
_refine_ls_wR_factor_gt          0.0585


_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      sigma
_refine_ls_weighting_details     
;
 Method= 
 SQRT(W) = 1/(Data with the key SIGMA(/FO/) in list 6) 
;

# 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 0.6456(4) 0.58588(13) 0.43777(13) 0.0266 1.0000 Uani D U . . . .
O1 O 0.4531(11) 0.6379(3) 0.0207(4) 0.0340(14) 1.0000 Uiso D U . . . .
O2 O 0.4482(11) 0.7041(3) 0.1391(4) 0.0334(14) 1.0000 Uiso D U . . . .
C1 C 0.8181(15) 0.5858(5) 0.2231(5) 0.0259(15) 1.0000 Uiso D U . . . .
C2 C 1.0094(15) 0.5196(5) 0.2566(5) 0.0254(15) 1.0000 Uiso D U . . . .
C3 C 1.0943(15) 0.4583(5) 0.2072(5) 0.0248(16) 1.0000 Uiso D U . . . .
C4 C 0.9960(16) 0.4556(4) 0.1225(5) 0.0257(16) 1.0000 Uiso D U . . . .
C5 C 0.8089(15) 0.5186(5) 0.0880(5) 0.0239(16) 1.0000 Uiso D U . . . .
C6 C 0.7257(14) 0.5818(5) 0.1391(5) 0.0261(15) 1.0000 Uiso D U . . . .
C7 C 0.7972(16) 0.6513(4) 0.3629(5) 0.0246(16) 1.0000 Uiso D U . . . .
C8 C 0.9582(17) 0.7150(5) 0.3980(5) 0.0277(16) 1.0000 Uiso D U . . . .
C9 C 0.9523(17) 0.7105(5) 0.4894(5) 0.0275(17) 1.0000 Uiso D U . . . .
C10 C 0.7885(12) 0.6473(4) 0.5195(5) 0.0263(16) 1.0000 Uiso D U . . . .
C11 C 0.7321(12) 0.6188(4) 0.6089(5) 0.0338(19) 1.0000 Uiso D U . . . .
C12 C 1.1418(18) 0.7697(5) 0.3447(5) 0.0284(16) 1.0000 Uiso D U . . . .
N1 N 0.7377(14) 0.6452(4) 0.2774(4) 0.0270(14) 1.0000 Uiso D U . . . .
N2 N 1.3057(14) 0.8087(4) 0.2968(4) 0.0322(16) 1.0000 Uiso D U . . . .
N3 N 0.5330(14) 0.6453(4) 0.0976(4) 0.0305(15) 1.0000 Uiso D U . . . .
H1 H 0.615(8) 0.682(2) 0.256(2) 0.032(4) 1.0000 Uiso D . . . . .
H2 H 1.0802 0.5191 0.3129 0.0322 1.0000 Uiso R . . . . .
H3 H 1.2252 0.4166 0.2300 0.0338 1.0000 Uiso R . . . . .
H4 H 1.0484 0.4117 0.0894 0.0329 1.0000 Uiso R . . . . .
H5 H 0.7437 0.5195 0.0314 0.0291 1.0000 Uiso R . . . . .
H111 H 0.8609 0.5700 0.6147 0.0772 1.0000 Uiso DR . . . . .
H112 H 0.8342 0.6562 0.6472 0.0769 1.0000 Uiso DR . . . . .
H113 H 0.4639 0.6120 0.6214 0.0771 1.0000 Uiso DR . . . . .
H114 H 1.0623 0.7481 0.5226 0.0333 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.453(2)
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 . C7 . 1.707(9) yes
S1 . C10 . 1.757(7) yes
O1 . N3 . 1.261(7) yes
O2 . N3 . 1.240(8) yes
C1 . C2 . 1.436(10) yes
C1 . C6 . 1.378(9) yes
C1 . N1 . 1.361(10) yes
C2 . C3 . 1.343(10) yes
C2 . H2 . 0.930 no
C3 . C4 . 1.392(9) yes
C3 . H3 . 0.934 no
C4 . C5 . 1.392(10) yes
C4 . H4 . 0.937 no
C5 . C6 . 1.382(11) yes
C5 . H5 . 0.929 no
C6 . N3 . 1.456(9) yes
C7 . C8 . 1.364(10) yes
C7 . N1 . 1.376(9) yes
C8 . C9 . 1.444(10) yes
C8 . C12 . 1.406(11) yes
C9 . C10 . 1.315(9) yes
C9 . H114 . 0.926 no
C10 . C11 . 1.500(10) yes
C11 . H111 . 0.963 no
C11 . H112 . 0.962 no
C11 . H113 . 0.959 no
C12 . N2 . 1.152(9) yes
N1 . H1 . 0.85(4) 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
C7 . S1 . C10 . 91.0(4) yes
C2 . C1 . C6 . 116.2(7) yes
C2 . C1 . N1 . 117.3(8) yes
C6 . C1 . N1 . 126.4(8) yes
C1 . C2 . C3 . 120.8(8) yes
C1 . C2 . H2 . 120.1 no
C3 . C2 . H2 . 119.1 no
C2 . C3 . C4 . 121.8(8) yes
C2 . C3 . H3 . 119.2 no
C4 . C3 . H3 . 119.0 no
C3 . C4 . C5 . 118.9(8) yes
C3 . C4 . H4 . 120.9 no
C5 . C4 . H4 . 120.2 no
C4 . C5 . C6 . 118.9(9) yes
C4 . C5 . H5 . 121.5 no
C6 . C5 . H5 . 119.6 no
C5 . C6 . C1 . 123.4(8) yes
C5 . C6 . N3 . 115.2(8) yes
C1 . C6 . N3 . 121.4(7) yes
S1 . C7 . C8 . 112.2(6) yes
S1 . C7 . N1 . 125.0(5) yes
C8 . C7 . N1 . 122.6(7) yes
C7 . C8 . C9 . 111.7(7) yes
C7 . C8 . C12 . 119.1(8) yes
C9 . C8 . C12 . 128.6(7) yes
C8 . C9 . C10 . 113.4(7) yes
C8 . C9 . H114 . 122.3 no
C10 . C9 . H114 . 124.3 no
S1 . C10 . C9 . 111.6(6) yes
S1 . C10 . C11 . 117.4(3) yes
C9 . C10 . C11 . 130.9(5) yes
C10 . C11 . H111 . 109.3 no
C10 . C11 . H112 . 109.3 no
H111 . C11 . H112 . 110.1 no
C10 . C11 . H113 . 109.3 no
H111 . C11 . H113 . 109.3 no
H112 . C11 . H113 . 109.5 no
C8 . C12 . N2 . 173.7(10) yes
C7 . N1 . C1 . 129.8(7) yes
C7 . N1 . H1 . 116(3) no
C1 . N1 . H1 . 114(3) no
C6 . N3 . O1 . 118.5(6) yes
C6 . N3 . O2 . 119.3(7) yes
O1 . N3 . O2 . 122.2(6) yes



# 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
0 5 1 x .
-2 12 3 x .
2 10 1 x .
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_chemical_name_common            ROY
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_ROY_ON_2p41GPa
_database_code_depnum_ccdc_archive 'CCDC 2098640'
loop_
_audit_author_name
_audit_author_address
'Nicholas Funnell'
;STFC, ISIS Neutron Facility
United Kingdom
;
_audit_update_record             
;
2021-07-22 deposited with the CCDC.	2021-08-27 downloaded from the CCDC.
;
_audit_creation_date             2021-01-26
_audit_creation_method           'CRYSTALS_ver_14.61_build_7795 '


_chemical_name_systematic        
;
5-methyl-2[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
;


#CheckCIF alerts
_vrf_THETM01_ROY_ON_2p41GPa      
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below. 
;
_vrf_PLAT027_ROY_ON_2p41GPa      
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      17.43 Degree
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below. 
;
_vrf_PLAT029_ROY_ON_2p41GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.727 Why?  
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below. 
;
_vrf_PLAT201_ROY_ON_2p41GPa      
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         17 Report
RESPONSE: The model could only be refined isotropically in order to maintain a 
favourable data-to-parameter ratio, due to numerous unmeasured reflections.
The relatively electron-rich sulfur atom has been modelled anisotropically.
;
_vrf_PLAT911_ROY_ON_2p41GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.555        402 Report
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below.  
;
_vrf_PLAT157_ROY_ON_2p41GPa      
;
PROBLEM: Non-standard Monoclinic Beta Angle less 90 Deg        89.36 Degree
RESPONSE: This is a series of high pressure structures where the beta angle
decreases, passing through 90 degrees. The non-standard beta angle allows the
change in angle to be followed clearly.
;
_vrf_PLAT340_ROY_ON_2p41GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00809 Ang.  
RESPONSE: These are poor-quality diffraction data.
;
_vrf_PLAT411_ROY_ON_2p41GPa      
;
PROBLEM: Short Inter H...H Contact  H5       ..H5       .       2.11 Ang.  
RESPONSE: These are high-pressure data - short contacts are expected.
;
_vrf_PLAT413_ROY_ON_2p41GPa      
;
PROBLEM: Short Inter XH3 .. XHn     H2       ..H111     .       2.10 Ang.  
RESPONSE: These are high-pressure data - short contacts are expected.
;
_vrf_PLAT910_ROY_ON_2p41GPa      
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).          8 Note  
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below. 
;


_refine_special_details          
; 
In the absence of significant anomalous scattering, Friedel pairs were 
merged. 

Data were collected in a Merrill-Bassett diamond anvil cell, which 
significantly restricts the regions over which reciprocal space can be sampled. 
Thus, these data are poor quality/incomplete, reflected in numerous CheckCIF 
alerts regarding refinement statistics. At all pressures, the atomic 
connectivity is known.

All non-sulfur atoms were refined isotropically; sulfur was refined 
anisotropically. Hydrogen atoms were constrained to ride on their host atoms.

#===============================================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#===============================================================================
Theta sin(th)/Lambda Complete  Expected Measured Total Missing
#-------------------------------------------------------------------------------
 20.82     0.500     0.713         1061      756      305
 23.01     0.550     0.701         1343      941      402
 23.24     0.555     0.700         1366      956      410
------------------------------------------------------------ ACTA Min. Res. ---

Note: The Reported Completeness refers to the Actual H,K,L Index Range
;


#end of refcif 
_cell_length_a                   3.59640(2)
_cell_length_b                   17.60380(6)
_cell_length_c                   15.95340(6)
_cell_angle_alpha                90
_cell_angle_beta                 89.358(7)
_cell_angle_gamma                90
_cell_volume                     1009.951(8)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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 0.1246 0.1234 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            4

# Given Formula = C12 H9 N3 O2 S1 
# Dc =      1.71 Fooo =    536.00 Mu =      3.17 M =    259.29
# Found Formula = C12 H9 N3 O2 S1 
# Dc =      1.71 FOOO =    536.00 Mu =      3.17 M =    259.29

_chemical_formula_sum            'C12 H9 N3 O2 S1'
_chemical_formula_moiety         'C12 H9 N3 O2 S1'
_chemical_compound_source        'TCI Chemicals'
_chemical_formula_weight         259.29


_cell_measurement_reflns_used    1445
_cell_measurement_theta_min      1.71
_cell_measurement_theta_max      23.26
_cell_measurement_temperature    293

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_max          0.248

_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.317

# Sheldrick geometric approximatio 0.98 0.98 
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_absorpt_correction_T_min  0.09
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Model from previously-determined structure'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      293
_diffrn_ambient_pressure         2410000
_diffrn_reflns_number            2325
_diffrn_reflns_av_unetI/netI     0.045
_reflns_number_total             977
_diffrn_reflns_av_R_equivalents  0.070
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 977 
# Theoretical number of reflections is about 2894 


_diffrn_reflns_theta_min         1.723
_diffrn_reflns_theta_max         23.236
_diffrn_measured_fraction_theta_max 0.688

_diffrn_reflns_theta_full        17.427
_diffrn_measured_fraction_theta_full 0.727


_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -3
_reflns_limit_h_max              3
_reflns_limit_k_min              0
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              15

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.77
_refine_diff_density_max         0.74


# 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     94
_refine_ls_number_parameters     82
_refine_ls_number_reflns         956
_oxford_refine_ls_R_factor_ref   0.1507
_refine_ls_R_factor_all          0.1507
_refine_ls_wR_factor_ref         0.0470
_refine_ls_wR_factor_all         0.0470
_refine_ls_goodness_of_fit_ref   1.0101
_refine_ls_shift/su_max          0.0002795
_refine_ls_shift/su_mean         0.0000515


# Computed with I/sigma = -10 
_oxford_reflns_number_all        956
_oxford_refine_ls_R_factor_all   0.1507
_oxford_refine_ls_wR_factor_all  0.0470

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                670
_refine_ls_R_factor_gt           0.1045
_refine_ls_wR_factor_gt          0.0435


_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      sigma
_refine_ls_weighting_details     
;
 Method= 
 SQRT(W) = 1/(Data with the key SIGMA(/FO/) in list 6) 
;

# 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 0.6920(3) 0.58857(9) 0.43475(10) 0.0374 1.0000 Uani D U . . . .
O1 O 0.4719(9) 0.6333(2) 0.0231(3) 0.0471(12) 1.0000 Uiso D U . . . .
O2 O 0.4780(9) 0.7006(2) 0.1379(3) 0.0458(11) 1.0000 Uiso D U . . . .
N1 N 0.7757(10) 0.6432(3) 0.2758(3) 0.0371(11) 1.0000 Uiso D U . . . .
N2 N 1.3161(11) 0.8078(3) 0.2950(3) 0.0403(13) 1.0000 Uiso D U . . . .
N3 N 0.5512(10) 0.6418(3) 0.0964(3) 0.0414(12) 1.0000 Uiso D U . . . .
C1 C 0.8414(12) 0.5849(4) 0.2239(4) 0.0367(12) 1.0000 Uiso D U . . . .
C2 C 1.0338(14) 0.5217(3) 0.2570(4) 0.0367(13) 1.0000 Uiso D U . . . .
C3 C 1.1095(12) 0.4597(3) 0.2068(4) 0.0358(13) 1.0000 Uiso D U . . . .
C4 C 0.9997(12) 0.4554(3) 0.1237(4) 0.0359(12) 1.0000 Uiso D U . . . .
C5 C 0.8242(12) 0.5175(3) 0.0917(4) 0.0369(12) 1.0000 Uiso D U . . . .
C6 C 0.7468(12) 0.5807(3) 0.1403(4) 0.0352(12) 1.0000 Uiso D U . . . .
C7 C 0.8338(11) 0.6511(3) 0.3602(4) 0.0354(12) 1.0000 Uiso D U . . . .
C8 C 0.9948(12) 0.7161(3) 0.3967(4) 0.0370(13) 1.0000 Uiso D U . . . .
C9 C 0.9962(12) 0.7116(3) 0.4829(4) 0.0401(14) 1.0000 Uiso D U . . . .
C10 C 0.8407(8) 0.6481(3) 0.5159(4) 0.0412(13) 1.0000 Uiso D U . . . .
C11 C 0.8020(8) 0.6215(2) 0.6023(3) 0.0420(15) 1.0000 Uiso D U . . . .
C12 C 1.1730(11) 0.7683(4) 0.3416(3) 0.0367(13) 1.0000 Uiso D U . . . .
H1 H 0.669(5) 0.6804(15) 0.2528(17) 0.046(3) 1.0000 Uiso D . . . . .
H2 H 1.1036 0.5219 0.3127 0.0402 1.0000 Uiso R . . . . .
H3 H 1.2448 0.4192 0.2282 0.0450 1.0000 Uiso R . . . . .
H4 H 1.0350 0.4108 0.0925 0.0479 1.0000 Uiso R . . . . .
H5 H 0.7660 0.5183 0.0351 0.0501 1.0000 Uiso R . . . . .
H9 H 1.1022 0.7492 0.5157 0.0480 1.0000 Uiso R . . . . .
H111 H 0.9225 0.5734 0.6079 0.0920 1.0000 Uiso DR . . . . .
H112 H 0.9119 0.6577 0.6394 0.0920 1.0000 Uiso DR . . . . .
H113 H 0.5438 0.6160 0.6163 0.0920 1.0000 Uiso DR . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.4974(15)
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 . C7 . 1.694(6) yes
S1 . C10 . 1.754(4) yes
O1 . N3 . 1.217(5) yes
O2 . N3 . 1.255(5) yes
N1 . C1 . 1.338(7) yes
N1 . C7 . 1.372(6) yes
N1 . H1 . 0.85(3) no
N2 . C12 . 1.138(6) yes
N3 . C6 . 1.468(7) yes
C1 . C2 . 1.415(8) yes
C1 . C6 . 1.383(7) yes
C2 . C3 . 1.378(6) yes
C2 . H2 . 0.927 no
C3 . C4 . 1.390(6) yes
C3 . H3 . 0.930 no
C4 . C5 . 1.365(7) yes
C4 . H4 . 0.937 no
C5 . C6 . 1.382(7) yes
C5 . H5 . 0.930 no
C7 . C8 . 1.411(8) yes
C8 . C9 . 1.378(6) yes
C8 . C12 . 1.419(7) yes
C9 . C10 . 1.355(7) yes
C9 . H9 . 0.928 no
C10 . C11 . 1.459(7) yes
C11 . H111 . 0.956 no
C11 . H112 . 0.959 no
C11 . H113 . 0.957 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
C7 . S1 . C10 . 92.2(3) yes
C1 . N1 . C7 . 131.1(6) yes
C1 . N1 . H1 . 114(2) no
C7 . N1 . H1 . 115.0(20) no
O2 . N3 . O1 . 124.0(5) yes
O2 . N3 . C6 . 116.9(6) yes
O1 . N3 . C6 . 119.1(5) yes
N1 . C1 . C2 . 117.2(6) yes
N1 . C1 . C6 . 126.5(6) yes
C2 . C1 . C6 . 116.3(5) yes
C1 . C2 . C3 . 120.0(6) yes
C1 . C2 . H2 . 119.5 no
C3 . C2 . H2 . 120.5 no
C2 . C3 . C4 . 122.8(6) yes
C2 . C3 . H3 . 119.7 no
C4 . C3 . H3 . 117.5 no
C3 . C4 . C5 . 116.7(6) yes
C3 . C4 . H4 . 120.9 no
C5 . C4 . H4 . 122.3 no
C4 . C5 . C6 . 121.8(6) yes
C4 . C5 . H5 . 119.0 no
C6 . C5 . H5 . 119.1 no
N3 . C6 . C1 . 123.0(5) yes
N3 . C6 . C5 . 114.7(6) yes
C1 . C6 . C5 . 122.3(6) yes
N1 . C7 . S1 . 125.1(4) yes
N1 . C7 . C8 . 123.7(5) yes
S1 . C7 . C8 . 111.1(5) yes
C7 . C8 . C9 . 111.8(5) yes
C7 . C8 . C12 . 117.0(6) yes
C9 . C8 . C12 . 130.4(6) yes
C8 . C9 . C10 . 115.5(5) yes
C8 . C9 . H9 . 121.9 no
C10 . C9 . H9 . 122.6 no
S1 . C10 . C9 . 109.5(5) yes
S1 . C10 . C11 . 118.6(2) yes
C9 . C10 . C11 . 131.8(4) yes
C10 . C11 . H111 . 109.5 no
C10 . C11 . H112 . 109.6 no
H111 . C11 . H112 . 109.9 no
C10 . C11 . H113 . 109.5 no
H111 . C11 . H113 . 109.2 no
H112 . C11 . H113 . 109.1 no
C8 . C12 . N2 . 177.2(9) yes



# 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
0 5 1 x .
3 8 0 x .
0 11 3 x .
1 13 4 x .
3 7 1 x .
2 6 12 x .
-3 1 7 x .
3 10 0 x .
1 8 1 x .
2 0 6 x .
0 13 4 x .
-1 3 9 x .
2 10 1 x .
2 10 1 x .
0 6 1 x .
-2 12 3 x .
1 3 9 x .
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_chemical_name_common            ROY
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_ROY_ON_3p00GPa
_database_code_depnum_ccdc_archive 'CCDC 2098641'
loop_
_audit_author_name
_audit_author_address
'Nicholas Funnell'
;STFC, ISIS Neutron Facility
United Kingdom
;
_audit_update_record             
;
2021-07-22 deposited with the CCDC.	2021-08-27 downloaded from the CCDC.
;
_audit_creation_date             2021-01-26
_audit_creation_method           'CRYSTALS_ver_14.61_build_7795 '


_chemical_name_systematic        
;
5-methyl-2[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
;


#CheckCIF alerts
_vrf_THETM01_ROY_ON_3p00GPa      
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below.  
;
_vrf_PLAT027_ROY_ON_3p00GPa      
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      17.44 Degree
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below. 
;
_vrf_PLAT029_ROY_ON_3p00GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.700 Why?  
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below.  
;
_vrf_PLAT201_ROY_ON_3p00GPa      
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         17 Report
RESPONSE: The model could only be refined isotropically in order to maintain a 
favourable data-to-parameter ratio, due to numerous unmeasured reflections.
The relatively electron-rich sulfur atom has been modelled anisotropically.
;
_vrf_PLAT911_ROY_ON_3p00GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.555        471 Report
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below. 
;
_vrf_PLAT157_ROY_ON_3p00GPa      
;
PROBLEM: Non-standard Monoclinic Beta Angle less 90 Deg        88.80 Degree
RESPONSE: This is a series of high pressure structures where the beta angle
decreases, passing through 90 degrees. The non-standard beta angle allows the
change in angle to be followed clearly.
;
_vrf_PLAT340_ROY_ON_3p00GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00745 Ang.  
RESPONSE: These are poor-quality diffraction data.
;
_vrf_PLAT413_ROY_ON_3p00GPa      
;
PROBLEM: Short Inter XH3 .. XHn     H2       ..H111     .       2.03 Ang.  
RESPONSE: These are high-pressure data - short contacts are expected.
;
_vrf_PLAT910_ROY_ON_3p00GPa      
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).          8 Note  
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below. 
;


_refine_special_details          
; 
In the absence of significant anomalous scattering, Friedel pairs were 
merged. 

Data were collected in a Merrill-Bassett diamond anvil cell, which 
significantly restricts the regions over which reciprocal space can be sampled. 
Thus, these data are poor quality/incomplete, reflected in numerous CheckCIF 
alerts regarding refinement statistics. At all pressures, the atomic 
connectivity is known.

All non-sulfur atoms were refined isotropically; sulfur was refined 
anisotropically. Hydrogen atoms were constrained to ride on their host atoms.


#===============================================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#===============================================================================
Theta sin(th)/Lambda Complete  Expected Measured Total Missing
#-------------------------------------------------------------------------------
 20.82     0.500     0.684         1049      717      332
 23.01     0.550     0.653         1326      866      460
 23.25     0.555     0.646         1355      876      479
------------------------------------------------------------ ACTA Min. Res. ---

Note: The Reported Completeness refers to the Actual H,K,L Index Range
;


#end of refcif 
_cell_length_a                   3.565200(17)
_cell_length_b                   17.43660(5)
_cell_length_c                   15.97730(5)
_cell_angle_alpha                90
_cell_angle_beta                 88.803(6)
_cell_angle_gamma                90
_cell_volume                     993.012(7)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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 0.1246 0.1234 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            4

# Given Formula = C12 H9 N3 O2 S1 
# Dc =      1.73 Fooo =    536.00 Mu =      3.22 M =    259.29
# Found Formula = C12 H9 N3 O2 S1 
# Dc =      1.73 FOOO =    536.00 Mu =      3.22 M =    259.29

_chemical_formula_sum            'C12 H9 N3 O2 S1'
_chemical_formula_moiety         'C12 H9 N3 O2 S1'
_chemical_compound_source        'TCI Chemicals'
_chemical_formula_weight         259.29


_cell_measurement_reflns_used    1445
_cell_measurement_theta_min      1.71
_cell_measurement_theta_max      23.26
_cell_measurement_temperature    293

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_max          0.248

_exptl_crystal_density_diffrn    1.734
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.322

# Sheldrick geometric approximatio 0.98 0.98 
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_absorpt_correction_T_min  0.09
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Model from previously-determined structure'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      293
_diffrn_ambient_pressure         3000000
_diffrn_reflns_number            2277
_diffrn_reflns_av_unetI/netI     0.036
_reflns_number_total             898
_diffrn_reflns_av_R_equivalents  0.036
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 898 
# Theoretical number of reflections is about 2852 


_diffrn_reflns_theta_min         1.729
_diffrn_reflns_theta_max         23.253
_diffrn_measured_fraction_theta_max 0.638

_diffrn_reflns_theta_full        17.440
_diffrn_measured_fraction_theta_full 0.700


_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -3
_reflns_limit_h_max              3
_reflns_limit_k_min              0
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              15

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.78
_refine_diff_density_max         0.61


# 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     94
_refine_ls_number_parameters     82
_refine_ls_number_reflns         876
_oxford_refine_ls_R_factor_ref   0.1234
_refine_ls_R_factor_all          0.1234
_refine_ls_wR_factor_ref         0.0481
_refine_ls_wR_factor_all         0.0481
_refine_ls_goodness_of_fit_ref   1.0701
_refine_ls_shift/su_max          0.0002431
_refine_ls_shift/su_mean         0.0000576


# Computed with I/sigma = -10 
_oxford_reflns_number_all        876
_oxford_refine_ls_R_factor_all   0.1234
_oxford_refine_ls_wR_factor_all  0.0481

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                681
_refine_ls_R_factor_gt           0.0885
_refine_ls_wR_factor_gt          0.0448


_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      sigma
_refine_ls_weighting_details     
;
 Method= 
 SQRT(W) = 1/(Data with the key SIGMA(/FO/) in list 6) 
;

# 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 0.6740(3) 0.58757(8) 0.43609(9) 0.0301 1.0000 Uani D U . . . .
O1 O 0.4653(8) 0.6347(2) 0.0224(3) 0.0373(10) 1.0000 Uiso D U . . . .
O2 O 0.4682(8) 0.7018(2) 0.1379(3) 0.0363(9) 1.0000 Uiso D U . . . .
C1 C 0.8370(10) 0.5855(3) 0.2231(3) 0.0293(11) 1.0000 Uiso D U . . . .
C2 C 1.0264(11) 0.5210(3) 0.2566(4) 0.0277(11) 1.0000 Uiso D U . . . .
C3 C 1.1048(9) 0.4586(3) 0.2068(3) 0.0274(12) 1.0000 Uiso D U . . . .
C4 C 0.9988(11) 0.4556(3) 0.1237(4) 0.0297(11) 1.0000 Uiso D U . . . .
C5 C 0.8164(11) 0.5182(3) 0.0902(4) 0.0295(11) 1.0000 Uiso D U . . . .
C6 C 0.7391(10) 0.5811(3) 0.1394(3) 0.0291(10) 1.0000 Uiso D U . . . .
C7 C 0.8202(11) 0.6524(3) 0.3598(4) 0.0282(11) 1.0000 Uiso D U . . . .
C8 C 0.9806(11) 0.7149(3) 0.3962(4) 0.0295(11) 1.0000 Uiso D U . . . .
C9 C 0.9762(10) 0.7105(3) 0.4846(3) 0.0292(11) 1.0000 Uiso D U . . . .
C10 C 0.8220(8) 0.6476(2) 0.5155(4) 0.0293(11) 1.0000 Uiso D U . . . .
C11 C 0.7743(8) 0.6222(2) 0.6053(3) 0.0342(13) 1.0000 Uiso D U . . . .
C12 C 1.1600(11) 0.7699(3) 0.3435(4) 0.0327(11) 1.0000 Uiso D U . . . .
N1 N 0.7625(9) 0.6445(3) 0.2748(3) 0.0289(10) 1.0000 Uiso D U . . . .
N2 N 1.3164(10) 0.8075(3) 0.2952(3) 0.0351(11) 1.0000 Uiso D U . . . .
N3 N 0.5459(9) 0.6432(3) 0.0967(3) 0.0337(10) 1.0000 Uiso D U . . . .
H1 H 0.641(5) 0.6797(13) 0.2523(16) 0.034(3) 1.0000 Uiso D . . . . .
H2 H 1.0966 0.5206 0.3123 0.0371 1.0000 Uiso R . . . . .
H3 H 1.2342 0.4171 0.2291 0.0378 1.0000 Uiso R . . . . .
H4 H 1.0459 0.4124 0.0911 0.0379 1.0000 Uiso R . . . . .
H5 H 0.7519 0.5195 0.0342 0.0381 1.0000 Uiso R . . . . .
H9 H 1.0777 0.7488 0.5177 0.0401 1.0000 Uiso R . . . . .
H111 H 0.8973 0.5738 0.6129 0.0522 1.0000 Uiso DR . . . . .
H112 H 0.8815 0.6596 0.6414 0.0520 1.0000 Uiso DR . . . . .
H113 H 0.5138 0.6167 0.6188 0.0520 1.0000 Uiso DR . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.5061(15)
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 . C7 . 1.735(6) yes
S1 . C10 . 1.735(5) yes
O1 . N3 . 1.236(5) yes
O2 . N3 . 1.243(5) yes
C1 . C2 . 1.422(7) yes
C1 . C6 . 1.391(7) yes
C1 . N1 . 1.343(6) yes
C2 . C3 . 1.374(7) yes
C2 . H2 . 0.929 no
C3 . C4 . 1.390(7) yes
C3 . H3 . 0.932 no
C4 . C5 . 1.385(7) yes
C4 . H4 . 0.928 no
C5 . C6 . 1.374(7) yes
C5 . H5 . 0.929 no
C6 . N3 . 1.461(6) yes
C7 . C8 . 1.367(7) yes
C7 . N1 . 1.383(6) yes
C8 . C9 . 1.414(7) yes
C8 . C12 . 1.420(7) yes
C9 . C10 . 1.318(7) yes
C9 . H9 . 0.931 no
C10 . C11 . 1.507(7) yes
C11 . H111 . 0.960 no
C11 . H112 . 0.956 no
C11 . H113 . 0.954 no
C12 . N2 . 1.148(6) yes
N1 . H1 . 0.84(2) 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
C7 . S1 . C10 . 91.7(3) yes
C2 . C1 . C6 . 116.7(5) yes
C2 . C1 . N1 . 117.6(6) yes
C6 . C1 . N1 . 125.7(5) yes
C1 . C2 . C3 . 120.1(6) yes
C1 . C2 . H2 . 120.4 no
C3 . C2 . H2 . 119.6 no
C2 . C3 . C4 . 121.8(5) yes
C2 . C3 . H3 . 119.3 no
C4 . C3 . H3 . 118.8 no
C3 . C4 . C5 . 118.6(5) yes
C3 . C4 . H4 . 121.1 no
C5 . C4 . H4 . 120.3 no
C4 . C5 . C6 . 119.9(6) yes
C4 . C5 . H5 . 121.2 no
C6 . C5 . H5 . 118.8 no
C1 . C6 . C5 . 122.9(5) yes
C1 . C6 . N3 . 122.6(4) yes
C5 . C6 . N3 . 114.5(5) yes
S1 . C7 . C8 . 110.0(4) yes
S1 . C7 . N1 . 125.2(4) yes
C8 . C7 . N1 . 124.7(5) yes
C7 . C8 . C9 . 112.7(5) yes
C7 . C8 . C12 . 118.3(5) yes
C9 . C8 . C12 . 128.6(4) yes
C8 . C9 . C10 . 114.5(5) yes
C8 . C9 . H9 . 122.1 no
C10 . C9 . H9 . 123.3 no
S1 . C10 . C9 . 111.0(5) yes
S1 . C10 . C11 . 119.3(2) yes
C9 . C10 . C11 . 129.7(3) yes
C10 . C11 . H111 . 109.6 no
C10 . C11 . H112 . 109.6 no
H111 . C11 . H112 . 109.5 no
C10 . C11 . H113 . 109.6 no
H111 . C11 . H113 . 109.1 no
H112 . C11 . H113 . 109.3 no
C8 . C12 . N2 . 172.3(7) yes
C7 . N1 . C1 . 130.4(5) yes
C7 . N1 . H1 . 116.0(18) no
C1 . N1 . H1 . 113.2(18) no
C6 . N3 . O2 . 117.6(5) yes
C6 . N3 . O1 . 118.7(4) yes
O2 . N3 . O1 . 123.6(4) yes



# 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 9 2 x .
1 3 9 x .
2 10 1 x .
-2 12 3 x .
0 8 2 x .
0 7 1 x .
0 14 5 x .
2 0 6 x .
-2 10 2 x .
-3 9 1 x .
3 8 0 x .
0 13 4 x .
1 8 1 x .
-2 1 8 x .
3 7 1 x .
1 17 7 x .
1 13 4 x .
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_chemical_name_common            ROY
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_ROY_ON_3p53GPa
_database_code_depnum_ccdc_archive 'CCDC 2098642'
loop_
_audit_author_name
_audit_author_address
'Nicholas Funnell'
;STFC, ISIS Neutron Facility
United Kingdom
;
_audit_update_record             
;
2021-07-22 deposited with the CCDC.	2021-08-27 downloaded from the CCDC.
;
_audit_creation_date             2021-01-26
_audit_creation_method           'CRYSTALS_ver_14.61_build_7795 '


_chemical_name_systematic        
;
5-methyl-2[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
;


#CheckCIF alerts
_vrf_THETM01_ROY_ON_3p53GPa      
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below. 
;
_vrf_PLAT027_ROY_ON_3p53GPa      
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      17.67 Degree
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below.  
;
_vrf_PLAT029_ROY_ON_3p53GPa      
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.718 Why?  
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below.  
;
_vrf_PLAT201_ROY_ON_3p53GPa      
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         17 Report
RESPONSE: The model could only be refined isotropically in order to maintain a 
favourable data-to-parameter ratio, due to numerous unmeasured reflections.
The relatively electron-rich sulfur atom has been modelled anisotropically.
;
_vrf_PLAT911_ROY_ON_3p53GPa      
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.555        399 Report
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below. 
;
_vrf_PLAT157_ROY_ON_3p53GPa      
;
PROBLEM: Non-standard Monoclinic Beta Angle less 90 Deg        88.36 Degree
RESPONSE: This is a series of high pressure structures where the beta angle
decreases, passing through 90 degrees. The non-standard beta angle allows the
change in angle to be followed clearly.
;
_vrf_PLAT340_ROY_ON_3p53GPa      
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00709 Ang.  
RESPONSE: These are poor-quality diffraction data.
;
_vrf_PLAT411_ROY_ON_3p53GPa      
;
PROBLEM: Short Inter H...H Contact  H5       ..H5       .       2.07 Ang.  
RESPONSE: These are high-pressure data - short contacts are expected.
;
_vrf_PLAT413_ROY_ON_3p53GPa      
;
PROBLEM: Short Inter XH3 .. XHn     H2       ..H111     .       2.03 Ang.  
RESPONSE: These are high-pressure data - short contacts are expected.
;
_vrf_PLAT910_ROY_ON_3p53GPa      
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).          8 Note  
RESPONSE: Data are highly incomplete owing to shading of recripocal space by 
the pressure cell. Resolution and completeness statistics are given below.  
;

_refine_special_details          
; 
In the absence of significant anomalous scattering, Friedel pairs were 
merged. 

Data were collected in a Merrill-Bassett diamond anvil cell, which 
significantly restricts the regions over which reciprocal space can be sampled. 
Thus, these data are poor quality/incomplete, reflected in numerous CheckCIF 
alerts regarding refinement statistics. At all pressures, the atomic 
connectivity is known.

All non-sulfur atoms were refined isotropically; sulfur was refined 
anisotropically. Hydrogen atoms were constrained to ride on their host atoms.


#===============================================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#===============================================================================
Theta sin(th)/Lambda Complete  Expected Measured Total Missing
#-------------------------------------------------------------------------------
 20.82     0.500     0.713         1025      731      294
 23.01     0.550     0.693         1301      902      399
 23.24     0.555     0.694         1332      925      407
------------------------------------------------------------ ACTA Min. Res. ---

Note: The Reported Completeness refers to the Actual H,K,L Index Range
;


#end of refcif 
_cell_length_a                   3.52400(2)
_cell_length_b                   17.38790(7)
_cell_length_c                   15.81840(7)
_cell_angle_alpha                90
_cell_angle_beta                 88.361(8)
_cell_angle_gamma                90
_cell_volume                     968.875(10)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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 0.1246 0.1234 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            4

# Given Formula = C12 H9 N3 O2 S1 
# Dc =      1.78 Fooo =    536.00 Mu =      3.30 M =    259.29
# Found Formula = C12 H9 N3 O2 S1 
# Dc =      1.78 FOOO =    536.00 Mu =      3.30 M =    259.29

_chemical_formula_sum            'C12 H9 N3 O2 S1'
_chemical_formula_moiety         'C12 H9 N3 O2 S1'
_chemical_compound_source        'TCI Chemicals'
_chemical_formula_weight         259.29


_cell_measurement_reflns_used    1358
_cell_measurement_theta_min      1.74
_cell_measurement_theta_max      23.34
_cell_measurement_temperature    293

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_max          0.248

_exptl_crystal_density_diffrn    1.777
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.330

# Sheldrick geometric approximatio 0.98 0.98 
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_absorpt_correction_T_min  0.07
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'USER DEFINED DATA COLLECTION'
_computing_cell_refinement       'USER DEFINED CELL REFINEMENT'
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Model from previously-determined structure'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      293
_diffrn_ambient_pressure         3530000
_diffrn_reflns_number            2425
_diffrn_reflns_av_unetI/netI     0.058
_reflns_number_total             936
_diffrn_reflns_av_R_equivalents  0.057
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 936 
# Theoretical number of reflections is about 2779 


_diffrn_reflns_theta_min         1.741
_diffrn_reflns_theta_max         23.243
_diffrn_measured_fraction_theta_max 0.679

_diffrn_reflns_theta_full        17.665
_diffrn_measured_fraction_theta_full 0.718


_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -3
_reflns_limit_h_max              3
_reflns_limit_k_min              0
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              15

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.83
_refine_diff_density_max         0.95


# 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     94
_refine_ls_number_parameters     82
_refine_ls_number_reflns         925
_oxford_refine_ls_R_factor_ref   0.1378
_refine_ls_R_factor_all          0.1378
_refine_ls_wR_factor_ref         0.0598
_refine_ls_wR_factor_all         0.0598
_refine_ls_goodness_of_fit_ref   1.0826
_refine_ls_shift/su_max          0.0001479
_refine_ls_shift/su_mean         0.0000479


# Computed with I/sigma = -10 
_oxford_reflns_number_all        925
_oxford_refine_ls_R_factor_all   0.1378
_oxford_refine_ls_wR_factor_all  0.0598

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                643
_refine_ls_R_factor_gt           0.0799
_refine_ls_wR_factor_gt          0.0553


_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      sigma
_refine_ls_weighting_details     
;
 Method= 
 SQRT(W) = 1/(Data with the key SIGMA(/FO/) in list 6) 
;

# 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 0.6586(3) 0.58693(7) 0.43699(9) 0.0284 1.0000 Uani D U . . . .
O1 O 0.4578(7) 0.6371(2) 0.0222(2) 0.0378(9) 1.0000 Uiso D U . . . .
O2 O 0.4560(7) 0.7026(2) 0.1390(2) 0.0352(9) 1.0000 Uiso D U . . . .
N1 N 0.7496(8) 0.6457(2) 0.2768(3) 0.0269(9) 1.0000 Uiso D U . . . .
N2 N 1.3063(9) 0.8078(2) 0.2947(3) 0.0334(10) 1.0000 Uiso D U . . . .
N3 N 0.5412(9) 0.6448(2) 0.0968(3) 0.0336(9) 1.0000 Uiso D U . . . .
C1 C 0.8244(10) 0.5860(3) 0.2222(3) 0.0272(10) 1.0000 Uiso D U . . . .
C2 C 1.0172(9) 0.5206(3) 0.2569(3) 0.0265(10) 1.0000 Uiso D U . . . .
C3 C 1.1001(9) 0.4581(3) 0.2072(3) 0.0274(10) 1.0000 Uiso D U . . . .
C4 C 1.0011(10) 0.4556(3) 0.1232(3) 0.0290(10) 1.0000 Uiso D U . . . .
C5 C 0.8162(9) 0.5166(3) 0.0890(3) 0.0276(10) 1.0000 Uiso D U . . . .
C6 C 0.7314(10) 0.5819(3) 0.1380(3) 0.0280(10) 1.0000 Uiso D U . . . .
C7 C 0.8067(10) 0.6512(3) 0.3628(3) 0.0243(10) 1.0000 Uiso D U . . . .
C8 C 0.9691(11) 0.7152(3) 0.3978(4) 0.0272(9) 1.0000 Uiso D U . . . .
C9 C 0.9676(10) 0.7118(3) 0.4875(3) 0.0297(10) 1.0000 Uiso D U . . . .
C10 C 0.8068(7) 0.6462(2) 0.5184(3) 0.0281(10) 1.0000 Uiso D U . . . .
C11 C 0.7564(8) 0.6211(2) 0.6069(4) 0.0377(12) 1.0000 Uiso D U . . . .
C12 C 1.1474(11) 0.7704(3) 0.3444(3) 0.0266(10) 1.0000 Uiso D U . . . .
H1 H 0.634(4) 0.6832(12) 0.2553(14) 0.034(3) 1.0000 Uiso D . . . . .
H2 H 1.0845 0.5203 0.3130 0.0311 1.0000 Uiso R . . . . .
H3 H 1.2297 0.4166 0.2294 0.0319 1.0000 Uiso R . . . . .
H4 H 1.0529 0.4120 0.0906 0.0360 1.0000 Uiso R . . . . .
H5 H 0.7535 0.5167 0.0321 0.0361 1.0000 Uiso R . . . . .
H9 H 1.0619 0.7511 0.5208 0.0401 1.0000 Uiso R . . . . .
H111 H 0.9136 0.5773 0.6168 0.0820 1.0000 Uiso DR . . . . .
H112 H 0.8267 0.6619 0.6440 0.0819 1.0000 Uiso DR . . . . .
H113 H 0.4958 0.6078 0.6181 0.0821 1.0000 Uiso DR . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.3906(9)
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 . C7 . 1.693(5) yes
S1 . C10 . 1.741(5) yes
O1 . N3 . 1.231(5) yes
O2 . N3 . 1.239(5) yes
N1 . C1 . 1.371(6) yes
N1 . C7 . 1.385(5) yes
N1 . H1 . 0.85(2) no
N2 . C12 . 1.153(5) yes
N3 . C6 . 1.446(6) yes
C1 . C2 . 1.442(6) yes
C1 . C6 . 1.382(6) yes
C2 . C3 . 1.367(6) yes
C2 . H2 . 0.926 no
C3 . C4 . 1.385(6) yes
C3 . H3 . 0.929 no
C4 . C5 . 1.365(6) yes
C4 . H4 . 0.932 no
C5 . C6 . 1.402(6) yes
C5 . H5 . 0.934 no
C7 . C8 . 1.375(7) yes
C8 . C9 . 1.420(6) yes
C8 . C12 . 1.413(6) yes
C9 . C10 . 1.359(6) yes
C9 . H9 . 0.930 no
C10 . C11 . 1.472(6) yes
C11 . H111 . 0.958 no
C11 . H112 . 0.958 no
C11 . H113 . 0.959 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
C7 . S1 . C10 . 91.6(3) yes
C1 . N1 . C7 . 129.8(5) yes
C1 . N1 . H1 . 114.7(16) no
C7 . N1 . H1 . 115.3(16) no
O2 . N3 . O1 . 122.9(4) yes
O2 . N3 . C6 . 118.6(5) yes
O1 . N3 . C6 . 118.4(4) yes
N1 . C1 . C2 . 116.3(5) yes
N1 . C1 . C6 . 126.8(5) yes
C2 . C1 . C6 . 116.9(5) yes
C1 . C2 . C3 . 120.3(5) yes
C1 . C2 . H2 . 120.3 no
C3 . C2 . H2 . 119.4 no
C2 . C3 . C4 . 121.4(5) yes
C2 . C3 . H3 . 120.0 no
C4 . C3 . H3 . 118.6 no
C3 . C4 . C5 . 119.4(5) yes
C3 . C4 . H4 . 120.4 no
C5 . C4 . H4 . 120.1 no
C4 . C5 . C6 . 120.5(5) yes
C4 . C5 . H5 . 120.8 no
C6 . C5 . H5 . 118.6 no
N3 . C6 . C5 . 117.2(5) yes
N3 . C6 . C1 . 121.4(5) yes
C5 . C6 . C1 . 121.4(5) yes
N1 . C7 . S1 . 125.8(4) yes
N1 . C7 . C8 . 121.7(5) yes
S1 . C7 . C8 . 112.3(4) yes
C7 . C8 . C9 . 112.3(5) yes
C7 . C8 . C12 . 119.4(5) yes
C9 . C8 . C12 . 127.9(4) yes
C8 . C9 . C10 . 112.6(4) yes
C8 . C9 . H9 . 123.0 no
C10 . C9 . H9 . 124.4 no
S1 . C10 . C9 . 111.2(4) yes
S1 . C10 . C11 . 119.82(17) yes
C9 . C10 . C11 . 129.0(3) yes
C10 . C11 . H111 . 109.7 no
C10 . C11 . H112 . 109.7 no
H111 . C11 . H112 . 109.1 no
C10 . C11 . H113 . 109.7 no
H111 . C11 . H113 . 109.4 no
H112 . C11 . H113 . 109.2 no
C8 . C12 . N2 . 171.6(6) yes



# 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 1 6 x .
-2 13 3 x .
1 5 11 x .
2 10 1 x .
0 7 1 x .
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
_chemical_name_common            ROY
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
