# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_Y_0.25_GPa
_database_code_depnum_ccdc_archive 'CCDC 1058322'
_audit_update_record             
;
2015-04-07 deposited with the CCDC.
2015-05-20 downloaded from the CCDC.
;
_audit_creation_date             14-12-16
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'ROY Y-form, 0.25 GPa'
_chemical_name_systematic        
5-methyl-2-((2-nitrophenyl)amino)-3-thiophenecarbonitrile


_exptl_special_details           
; 
The crystal was loaded in a Merrill-Bassett diamond anvil cell, using 4:1 
methanol:ethanol as a pressure-transmitting medium and ruby as a pressure 
marker. Pressure was measured before and after data collection and the average
of these - 0.25 GPa - was taken to be the experimental pressure.
;
_refine_special_details          
; 
CheckCif alerts

PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      18.52 Degree
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......      0.528 Note  
PLAT340_ALERT_3_B Low Bond Precision on  C-C Bonds ...............     0.0185 Ang.  
PLAT911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L=  0.588        913 Report
RFACG01_ALERT_3_C  The value of the R factor is > 0.10      R factor given   0.105
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5879
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large.      17.09 Why ?
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          39 %     
PLAT960_ALERT_3_G Number of Intensities with I  <   - 2*sig(I) ...          3 Check 

Much of reciprocal space is unmeasurable, owing to the body of the diamond 
anvil cell, leading to missing reflections, low completeness and poor statistics.
Data are 50.4% complete to 0.85 Angstroms. Resolution and completeness 
statistics are given below.

#====================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#====================================================
Theta sin(th)/Lambda Complete  Expected Measured  Missing
#-------------------------------------------------------------------------------
 20.82     0.500     0.534         1185      633      552
 23.01     0.550     0.520         1572      818      754
 24.70     0.588     0.516         1885      972      913
------------------------------------------------------------ ACTA Min. Res. ---


PLAT921_ALERT_1_B R1  in the CIF and FCF Differ by ...............    -0.0192 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......    109.731 Check

Crystals labels omitted reflections with several different flags that describe 
the reason for their omission. PLATON does not recognise this format and 
these omitted reflections have been included in the calculation of R1 and K.

 
PLAT201_ALERT_2_A Isotropic non-H Atoms in Main Residue(s) .......         17 Report
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         18 Note  
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         18 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         64 Note  

Owing to poor data quality, only the relatively electron-rich sulfur atom could be 
refined anisotropically. Distance, vibration and thermal similarity restraints were 
necessary for a stable refinement. Previous variable-pressure experiments on 
organic materials have shown that pressure has little effect on covalent bond 
lengths and so the model has been restrained to the values observed at ambient 
pressure. The refinement procedure is discussed above and the restraints used 
are given at the end of this file.


PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do ! 

These are given further below

 
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check 
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check 

This is correct
;


_cell_length_a                   8.412(3)
_cell_length_b                   15.9905(15)
_cell_length_c                   8.469(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.55(3)
_cell_angle_gamma                90
_cell_volume                     1138.7(5)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,-y+1/2,z+1/2
-x+1/2,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 =      1.51 Fooo =    536.00 Mu =      2.81 M =    259.29
# Found Formula = C12 H9 N3 O2 S1 
# Dc =      1.51 FOOO =    536.00 Mu =      2.81 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    1655
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25
_cell_measurement_temperature    293

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.097
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_max          0.165

_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.281

# Sheldrick geometric approximatio 0.97 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.97
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ


_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'User-defined model'
_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         0.25 #GPa
_diffrn_reflns_number            7186
_reflns_number_total             976
_diffrn_reflns_av_R_equivalents  0.099
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 976 
# Theoretical number of reflections is about 3877 


_diffrn_reflns_theta_min         2.547
_diffrn_reflns_theta_max         24.699
_diffrn_measured_fraction_theta_max 0.504

_diffrn_reflns_theta_full        18.524
_diffrn_measured_fraction_theta_full 0.528


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_reflns_limit_h_min              -8
_reflns_limit_h_max              5
_reflns_limit_k_min              0
_reflns_limit_k_max              18
_reflns_limit_l_min              0
_reflns_limit_l_max              9

_oxford_diffrn_Wilson_B_factor   2.57
_oxford_diffrn_Wilson_scale      0.48

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

_refine_diff_density_min         -0.79
_refine_diff_density_max         0.79


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         966
_refine_ls_number_restraints     64
_refine_ls_number_parameters     78
_oxford_refine_ls_R_factor_ref   0.1490
_refine_ls_wR_factor_ref         0.2212
_refine_ls_goodness_of_fit_ref   0.9588
_refine_ls_shift/su_max          0.0000473
_refine_ls_shift/su_mean         0.0000094


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        966
_refine_ls_R_factor_all          0.1490
_refine_ls_wR_factor_all         0.2212

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                668
_refine_ls_R_factor_gt           0.1048
_refine_ls_wR_factor_gt          0.1888


_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.00P)² +17.09P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

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


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 0.7950(5) 0.38593(16) 0.1151(5) 0.0434 1.0000 Uani D U . . . .
C2 C 0.9870(16) 0.3507(6) 0.0892(15) 0.0387(15) 1.0000 Uiso D U . . . .
C3 C 1.0429(18) 0.3068(6) 0.2147(15) 0.0380(15) 1.0000 Uiso D U . . . .
C4 C 0.9250(16) 0.2996(6) 0.3346(14) 0.0382(14) 1.0000 Uiso D U . . . .
C5 C 0.7855(16) 0.3389(6) 0.2962(14) 0.0362(13) 1.0000 Uiso D U . . . .
C7 C 0.6367(16) 0.3935(6) 0.5185(15) 0.0405(13) 1.0000 Uiso D U . . . .
C8 C 0.7736(18) 0.4362(6) 0.5820(15) 0.0436(15) 1.0000 Uiso D U . . . .
C9 C 0.7620(19) 0.4881(6) 0.7095(17) 0.0462(16) 1.0000 Uiso D U . . . .
C10 C 0.6207(18) 0.4954(7) 0.7873(18) 0.0468(16) 1.0000 Uiso D U . . . .
C11 C 0.4875(19) 0.4557(6) 0.7349(16) 0.0448(16) 1.0000 Uiso D U . . . .
C12 C 0.4953(17) 0.4031(6) 0.6027(16) 0.0438(13) 1.0000 Uiso D U . . . .
C16 C 0.9464(19) 0.2542(6) 0.4797(15) 0.0424(16) 1.0000 Uiso D U . . . .
C18 C 1.068(2) 0.3714(6) -0.0625(17) 0.0397(18) 1.0000 Uiso D U . . . .
N6 N 0.6485(16) 0.3438(5) 0.3862(13) 0.0378(13) 1.0000 Uiso D U . . . .
N13 N 0.3485(15) 0.3646(5) 0.5476(14) 0.0476(14) 1.0000 Uiso D U . . . .
N17 N 0.9559(17) 0.2166(5) 0.5935(15) 0.0480(19) 1.0000 Uiso D U . . . .
O14 O 0.2247(15) 0.3795(5) 0.6183(13) 0.0544(17) 1.0000 Uiso D U . . . .
O15 O 0.3443(15) 0.3160(4) 0.4351(13) 0.0513(16) 1.0000 Uiso D U . . . .
H31 H 1.1436 0.2835 0.2237 0.0459 1.0000 Uiso R . . . . .
H81 H 0.8711 0.4288 0.5362 0.0518 1.0000 Uiso R . . . . .
H91 H 0.8507 0.5185 0.7434 0.0563 1.0000 Uiso R . . . . .
H101 H 0.6167 0.5289 0.8778 0.0563 1.0000 Uiso R . . . . .
H111 H 0.3919 0.4621 0.7858 0.0540 1.0000 Uiso R . . . . .
H183 H 1.1745 0.3498 -0.0578 0.0600 1.0000 Uiso R . . . . .
H182 H 1.0722 0.4308 -0.0765 0.0599 1.0000 Uiso R . . . . .
H181 H 1.0102 0.3457 -0.1495 0.0598 1.0000 Uiso R . . . . .
H61 H 0.5669 0.3158 0.3564 0.0450 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.053(3) 0.0389(13) 0.039(2) 0.0071(14) 0.013(2) 0.0091(16)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.58(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . C2 . 1.730(12) yes
S1 . C5 . 1.712(11) yes
C2 . C3 . 1.349(15) yes
C2 . C18 . 1.507(11) yes
C3 . C4 . 1.443(11) yes
C3 . H31 . 0.926 no
C4 . C5 . 1.362(15) yes
C4 . C16 . 1.434(14) yes
C5 . N6 . 1.401(11) yes
C7 . C8 . 1.431(16) yes
C7 . C12 . 1.412(12) yes
C7 . N6 . 1.379(12) yes
C8 . C9 . 1.368(13) yes
C8 . H81 . 0.924 no
C9 . C10 . 1.380(13) yes
C9 . H91 . 0.928 no
C10 . C11 . 1.353(16) yes
C10 . H101 . 0.936 no
C11 . C12 . 1.403(13) yes
C11 . H111 . 0.929 no
C12 . N13 . 1.445(15) yes
C16 . N17 . 1.136(13) yes
C18 . H183 . 0.961 no
C18 . H182 . 0.958 no
C18 . H181 . 0.963 no
N6 . H61 . 0.852 no
N13 . O14 . 1.238(11) yes
N13 . O15 . 1.230(11) yes
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
C2 . S1 . C5 . 92.1(6) yes
S1 . C2 . C3 . 112.1(8) yes
S1 . C2 . C18 . 118.8(11) yes
C3 . C2 . C18 . 129.1(11) yes
C2 . C3 . C4 . 111.4(12) yes
C2 . C3 . H31 . 124.9 no
C4 . C3 . H31 . 123.7 no
C3 . C4 . C5 . 113.6(11) yes
C3 . C4 . C16 . 124.8(12) yes
C5 . C4 . C16 . 121.7(9) yes
S1 . C5 . C4 . 110.8(7) yes
S1 . C5 . N6 . 121.4(10) yes
C4 . C5 . N6 . 127.8(11) yes
C8 . C7 . C12 . 116.0(10) yes
C8 . C7 . N6 . 120.4(10) yes
C12 . C7 . N6 . 123.6(12) yes
C7 . C8 . C9 . 120.9(11) yes
C7 . C8 . H81 . 119.7 no
C9 . C8 . H81 . 119.4 no
C8 . C9 . C10 . 120.6(14) yes
C8 . C9 . H91 . 119.2 no
C10 . C9 . H91 . 120.2 no
C9 . C10 . C11 . 121.4(13) yes
C9 . C10 . H101 . 119.3 no
C11 . C10 . H101 . 119.3 no
C10 . C11 . C12 . 119.1(12) yes
C10 . C11 . H111 . 121.1 no
C12 . C11 . H111 . 119.8 no
C7 . C12 . C11 . 121.8(12) yes
C7 . C12 . N13 . 120.9(11) yes
C11 . C12 . N13 . 117.0(10) yes
C4 . C16 . N17 . 176.5(17) yes
C2 . C18 . H183 . 109.2 no
C2 . C18 . H182 . 110.0 no
H183 . C18 . H182 . 108.8 no
C2 . C18 . H181 . 109.2 no
H183 . C18 . H181 . 109.2 no
H182 . C18 . H181 . 110.4 no
C5 . N6 . C7 . 123.5(12) yes
C5 . N6 . H61 . 118.6 no
C7 . N6 . H61 . 117.9 no
C12 . N13 . O14 . 119.0(10) yes
C12 . N13 . O15 . 121.7(9) yes
O14 . N13 . O15 . 119.3(12) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 16/12/14 at 13:27:24
#
#Refinement with riding constraints on H atoms
#LIST     12                                                                    
BLOCK SCALE X'S, 
CONT S(1,U'S) 
CONT C(2,U[ISO]) UNTIL O(15) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  18,X'S) H   ( 183,X'S) H   ( 182,X'S) H   ( 181,X'S) 
RIDE N   (   6,X'S) H   (  61,X'S) 
END  

#Refinement of hydrogen positions and U[iso] with restraints
#LIST 12
block
CONT H(   31 ,X,Y,Z,U[ISO])
CONT H(   81 ,X,Y,Z,U[ISO])
CONT H(   91 ,X,Y,Z,U[ISO])
CONT H(  101 ,X,Y,Z,U[ISO])
CONT H(  111 ,X,Y,Z,U[ISO])
CONT H(  183 ,X,Y,Z,U[ISO])
CONT H(  182 ,X,Y,Z,U[ISO])
CONT H(  181 ,X,Y,Z,U[ISO])
CONT H(   61 ,X,Y,Z,U[ISO])
END
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 16/12/14 at 13:27:24
#
#Non-H atom restraints
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
REM   DELU   START (DO NOT REMOVE THIS LINE) 
VIBR .0, 0.00200 = S(1) TO C(2) 
VIBR .0, 0.00200 = S(1) TO C(5) 
VIBR .0, 0.00500 = C(5) TO C(2) 
VIBR .0, 0.00200 = C(2) TO C(18) 
VIBR .0, 0.00200 = C(2) TO C(3) 
VIBR .0, 0.00500 = C(18) TO S(1) 
VIBR .0, 0.00500 = C(3) TO S(1) 
VIBR .0, 0.00500 = C(3) TO C(18) 
VIBR .0, 0.00200 = C(3) TO C(4) 
VIBR .0, 0.00500 = C(4) TO C(2) 
VIBR .0, 0.00200 = C(4) TO C(5) 
VIBR .0, 0.00200 = C(4) TO C(16) 
VIBR .0, 0.00500 = C(5) TO C(3) 
VIBR .0, 0.00500 = C(16) TO C(3) 
VIBR .0, 0.00500 = C(16) TO C(5) 
VIBR .0, 0.00200 = C(5) TO N(6) 
VIBR .0, 0.00500 = S(1) TO C(4) 
VIBR .0, 0.00500 = N(6) TO C(4) 
VIBR .0, 0.00500 = N(6) TO S(1) 
VIBR .0, 0.00200 = N(6) TO C(7) 
VIBR .0, 0.00500 = C(7) TO C(5) 
VIBR .0, 0.00200 = C(7) TO C(8) 
VIBR .0, 0.00200 = C(7) TO C(12) 
VIBR .0, 0.00500 = C(8) TO N(6) 
VIBR .0, 0.00500 = C(12) TO N(6) 
VIBR .0, 0.00500 = C(12) TO C(8) 
VIBR .0, 0.00200 = C(8) TO C(9) 
VIBR .0, 0.00500 = C(9) TO C(7) 
VIBR .0, 0.00200 = C(9) TO C(10) 
VIBR .0, 0.00500 = C(10) TO C(8) 
VIBR .0, 0.00200 = C(10) TO C(11) 
VIBR .0, 0.00500 = C(11) TO C(9) 
VIBR .0, 0.00200 = C(11) TO C(12) 
VIBR .0, 0.00500 = C(12) TO C(10) 
VIBR .0, 0.00200 = C(12) TO N(13) 
VIBR .0, 0.00500 = C(7) TO C(11) 
VIBR .0, 0.00500 = N(13) TO C(11) 
VIBR .0, 0.00500 = N(13) TO C(7) 
VIBR .0, 0.00200 = N(13) TO O(14) 
VIBR .0, 0.00200 = N(13) TO O(15) 
VIBR .0, 0.00500 = O(14) TO C(12) 
VIBR .0, 0.00500 = O(15) TO C(12) 
VIBR .0, 0.00500 = O(15) TO O(14) 
VIBR .0, 0.00200 = C(16) TO N(17) 
VIBR .0, 0.00500 = N(17) TO C(4) 
REM   DELU   END (DO NOT REMOVE THIS LINE) 
REM   THERMSIM   START (DO NOT REMOVE THIS LINE) 
U(IJ) .0, 0.04000 = S(1) TO C(2) 
U(IJ) .0, 0.04000 = S(1) TO C(5) 
U(IJ) .0, 0.08000 = C(2) TO C(18) 
U(IJ) .0, 0.04000 = C(2) TO C(3) 
U(IJ) .0, 0.04000 = C(3) TO C(4) 
U(IJ) .0, 0.04000 = C(4) TO C(5) 
U(IJ) .0, 0.04000 = C(4) TO C(16) 
U(IJ) .0, 0.04000 = C(5) TO N(6) 
U(IJ) .0, 0.04000 = N(6) TO C(7) 
U(IJ) .0, 0.04000 = C(7) TO C(8) 
U(IJ) .0, 0.04000 = C(7) TO C(12) 
U(IJ) .0, 0.04000 = C(8) TO C(9) 
U(IJ) .0, 0.04000 = C(9) TO C(10) 
U(IJ) .0, 0.04000 = C(10) TO C(11) 
U(IJ) .0, 0.04000 = C(11) TO C(12) 
U(IJ) .0, 0.04000 = C(12) TO N(13) 
U(IJ) .0, 0.08000 = N(13) TO O(14) 
U(IJ) .0, 0.08000 = N(13) TO O(15) 
U(IJ) .0, 0.08000 = C(16) TO N(17) 
REM   THERMSIM   END (DO NOT REMOVE THIS LINE) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
DISTANCE 1.220000 , 0.020000 = N(13) TO O(14) 
DISTANCE 1.220000 , 0.020000 = N(13) TO O(15) 
DISTANCE 1.450000 , 0.020000 = C(12) TO N(13) 
DISTANCE 1.390000 , 0.020000 = C(11) TO C(12) 
DISTANCE 1.360000 , 0.020000 = C(10) TO C(11) 
DISTANCE 1.390000 , 0.020000 = C(9) TO C(10) 
DISTANCE 1.370000 , 0.020000 = C(8) TO C(9) 
DISTANCE 1.400000 , 0.020000 = C(7) TO C(8) 
DISTANCE 1.410000 , 0.020000 = C(7) TO C(12) 
DISTANCE 1.370000 , 0.020000 = C(7) TO N(6) 
DISTANCE 1.400000 , 0.02000 = C(5) TO N(6) 
DISTANCE 1.720000 , 0.020000 = S(1) TO C(5) 
DISTANCE 1.720000 , 0.020000 = S(1) TO C(2) 
DISTANCE 1.350000 , 0.020000 = C(2) TO C(3) 
DISTANCE 1.430000 , 0.020000 = C(3) TO C(4) 
DISTANCE 1.360000 , 0.020000 = C(4) TO C(5) 
DISTANCE 1.430000 , 0.020000 = C(4) TO C(16) 
DISTANCE 1.140000 , 0.020000 = C(16) TO N(17) 
DISTANCE 1.500000 , 0.020000 = C(2) TO C(18) 
END                

#Restraints used for hydrogen refinement
#LIST 16
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 3) to H(31) 
REST 0.046, 0.002 = H(31,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(31) TO C ( 3) TO C(2) 
CONT H(31) TO C ( 3) TO C(4) 
PLANAR C ( 3) C(2) C(4) H(31) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 8) to H(81) 
REST 0.052, 0.002 = H(81,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(81) TO C ( 8) TO C(7) 
CONT H(81) TO C ( 8) TO C(9) 
PLANAR C ( 8) C(7) C(9) H(81) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 9) to H(91) 
REST 0.056, 0.002 = H(91,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(91) TO C ( 9) TO C(8) 
CONT H(91) TO C ( 9) TO C(10) 
PLANAR C ( 9) C(8) C(10) H(91) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 10) to H(101) 
REST 0.056, 0.002 = H(101,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(101) TO C ( 10) TO C(9) 
CONT H(101) TO C ( 10) TO C(11) 
PLANAR C ( 10) C(9) C(11) H(101) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 11) to H(111) 
REST 0.054, 0.002 = H(111,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(111) TO C ( 11) TO C(10) 
CONT H(111) TO C ( 11) TO C(12) 
PLANAR C ( 11) C(10) C(12) H(111) 
REM            3 H on sp 3
DIST 0.96, 0.02 = 
CONT C ( 18) to H(183) 
CONT C ( 18) to H(182) 
CONT C ( 18) to H(181) 
REST 0.060, 0.002 = H(183,U[ISO]) 
REST 0.060, 0.002 = H(182,U[ISO]) 
REST 0.060, 0.002 = H(181,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(2) to C ( 18) to H(183) 
CONT C(2) to C ( 18) to H(182) 
CONT C(2) to C ( 18) to H(181) 
ANGLE 0.0, 2.0 = mean H(183) to C ( 18) to H(182) 
CONT H(183) to C ( 18) to H(181) 
CONT H(182) to C ( 18) to H(181) 
REM            H1-N-R2
DIST 0.86, 0.02 = 
CONT N ( 6) to H(61) 
REST 0.045, 0.002 = H(61,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(61) TO N ( 6) TO C(5) 
CONT H(61) TO N ( 6) TO C(7) 
PLANAR 0.010000  C(5) C(7) N(6) H(61) 
END
;

# 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
-6 1 3 x .
-5 2 2 x .
-3 1 1 x .
-4 3 1 x .
_chemical_name_common            ROY
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_Y_0.54_GPa
_database_code_depnum_ccdc_archive 'CCDC 1058323'
_audit_update_record             
;
2015-04-07 deposited with the CCDC.
2015-05-20 downloaded from the CCDC.
;
_audit_creation_date             14-12-16
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'ROY Y-form, 0.54 GPa'
_chemical_name_systematic        
5-methyl-2-((2-nitrophenyl)amino)-3-thiophenecarbonitrile


_exptl_special_details           
; 
The crystal was loaded in a Merrill-Bassett diamond anvil cell, using 4:1 
methanol:ethanol as a pressure-transmitting medium and ruby as a pressure 
marker. Pressure was measured before and after data collection and the average
of these - 0.54 GPa - was taken to be the experimental pressure.
;

_refine_special_details          
; 
CheckCif alerts

PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      18.52 Degree
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......      0.511 Note  
PLAT340_ALERT_3_B Low Bond Precision on  C-C Bonds ...............     0.0165 Ang.  
PLAT911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L=  0.588        929 Report
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5879
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large.      12.14 Why ? 
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          40 %     
PLAT960_ALERT_3_G Number of Intensities with I  <   - 2*sig(I) ...          2 Check 

Much of reciprocal space is unmeasurable, owing to the body of the diamond 
anvil cell, leading to missing reflections, low completeness and poor statistics.
Data are 48.3% complete to 0.85 Angstroms. Resolution and completeness 
statistics are given below.

#===============================================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#===============================================================================
Theta sin(th)/Lambda Complete  Expected Measured  Missing
#-------------------------------------------------------------------------------
 20.82     0.500     0.521         1168      608      560
 23.01     0.550     0.504         1545      779      766
 24.70     0.588     0.496         1842      913      929
------------------------------------------------------------ ACTA Min. Res. ---


PLAT921_ALERT_1_B R1  in the CIF and FCF Differ by ...............    -0.0193 Check 
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......    135.310 Check 

Crystals labels omitted reflections with several different flags that describe 
the reason for their omission. PLATON does not recognise this format and 
these omitted reflections have been included in the calculation of R1 and K.


PLAT201_ALERT_2_A Isotropic non-H Atoms in Main Residue(s) .......         17 Report
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         18 Note  
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         18 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         64 Note  

Owing to poor data quality, only the relatively electron-rich sulfur atom could be 
refined anisotropically. Distance, vibration and thermal similarity restraints were 
necessary for a stable refinement. Previous variable-pressure experiments on 
organic materials have shown that pressure has little effect on covalent bond 
lengths and so the model has been restrained to the values observed at ambient 
pressure. The refinement procedure is discussed above and the restraints used 
are given at the end of this file.


PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do ! 

These are given further below.


PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check 
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check 

This is correct.


PLAT432_ALERT_2_G Short Inter X...Y Contact  O14    ..  C18     ..       3.00 Ang.

Short contacts are not unusual for high-pressure structures.
;


_cell_length_a                   8.337(3)
_cell_length_b                   15.8027(14)
_cell_length_c                   8.4626(19)
_cell_angle_alpha                90
_cell_angle_beta                 91.44(3)
_cell_angle_gamma                90
_cell_volume                     1114.6(5)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-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 =      2.87 M =    259.29
# Found Formula = C12 H9 N3 O2 S1 
# Dc =      1.55 FOOO =    536.00 Mu =      2.87 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    1739
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25
_cell_measurement_temperature    293

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.097
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_max          0.165

_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.287

# Sheldrick geometric approximatio 0.97 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.97
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ


_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'User-defined model'
_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         0.54 #GPa
_diffrn_reflns_number            6766
_reflns_number_total             913
_diffrn_reflns_av_R_equivalents  0.087
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 913 
# Theoretical number of reflections is about 3794 


_diffrn_reflns_theta_min         2.578
_diffrn_reflns_theta_max         24.696
_diffrn_measured_fraction_theta_max 0.483

_diffrn_reflns_theta_full        18.522
_diffrn_measured_fraction_theta_full 0.511


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_reflns_limit_h_min              -8
_reflns_limit_h_max              5
_reflns_limit_k_min              0
_reflns_limit_k_max              18
_reflns_limit_l_min              0
_reflns_limit_l_max              9

_oxford_diffrn_Wilson_B_factor   2.50
_oxford_diffrn_Wilson_scale      0.44

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

_refine_diff_density_min         -0.88
_refine_diff_density_max         0.80


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>0.0\s(I)
_refine_ls_number_reflns         907
_refine_ls_number_restraints     64
_refine_ls_number_parameters     78
_oxford_refine_ls_R_factor_ref   0.1285
_refine_ls_wR_factor_ref         0.1813
_refine_ls_goodness_of_fit_ref   0.9407
_refine_ls_shift/su_max          0.0000474
_refine_ls_shift/su_mean         0.0000117


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        907
_refine_ls_R_factor_all          0.1285
_refine_ls_wR_factor_all         0.1813

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                646
_refine_ls_R_factor_gt           0.0925
_refine_ls_wR_factor_gt          0.1603

_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.00P)² +12.14P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

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


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 0.7955(5) 0.38583(14) 0.1130(4) 0.0390 1.0000 Uani D U . . . .
C2 C 0.9891(15) 0.3502(5) 0.0868(13) 0.0355(14) 1.0000 Uiso D U . . . .
C3 C 1.0452(16) 0.3054(5) 0.2120(13) 0.0353(14) 1.0000 Uiso D U . . . .
C4 C 0.9260(15) 0.2977(5) 0.3321(13) 0.0347(13) 1.0000 Uiso D U . . . .
C5 C 0.7884(15) 0.3386(5) 0.2961(12) 0.0323(12) 1.0000 Uiso D U . . . .
C7 C 0.6374(15) 0.3928(5) 0.5186(13) 0.0365(12) 1.0000 Uiso D U . . . .
C8 C 0.7719(16) 0.4357(5) 0.5812(14) 0.0398(14) 1.0000 Uiso D U . . . .
C9 C 0.7641(17) 0.4870(5) 0.7114(15) 0.0431(15) 1.0000 Uiso D U . . . .
C10 C 0.6199(16) 0.4959(6) 0.7877(15) 0.0422(15) 1.0000 Uiso D U . . . .
C11 C 0.4863(17) 0.4554(5) 0.7357(14) 0.0405(14) 1.0000 Uiso D U . . . .
C12 C 0.4948(15) 0.4036(5) 0.6026(14) 0.0398(12) 1.0000 Uiso D U . . . .
C16 C 0.9510(17) 0.2537(5) 0.4779(13) 0.0392(15) 1.0000 Uiso D U . . . .
C18 C 1.0721(18) 0.3707(5) -0.0652(14) 0.0368(16) 1.0000 Uiso D U . . . .
N6 N 0.6467(14) 0.3435(4) 0.3843(11) 0.0334(12) 1.0000 Uiso D U . . . .
N13 N 0.3457(14) 0.3652(5) 0.5471(12) 0.0441(13) 1.0000 Uiso D U . . . .
N17 N 0.9586(15) 0.2168(5) 0.5930(13) 0.0460(17) 1.0000 Uiso D U . . . .
O14 O 0.2200(13) 0.3828(4) 0.6163(11) 0.0528(15) 1.0000 Uiso D U . . . .
O15 O 0.3450(13) 0.3164(4) 0.4367(11) 0.0486(15) 1.0000 Uiso D U . . . .
H31 H 1.1469 0.2825 0.2210 0.0419 1.0000 Uiso R . . . . .
H81 H 0.8695 0.4300 0.5329 0.0480 1.0000 Uiso R . . . . .
H91 H 0.8560 0.5160 0.7470 0.0522 1.0000 Uiso R . . . . .
H101 H 0.6155 0.5306 0.8768 0.0513 1.0000 Uiso R . . . . .
H111 H 0.3898 0.4611 0.7875 0.0493 1.0000 Uiso R . . . . .
H181 H 1.1806 0.3509 -0.0562 0.0550 1.0000 Uiso R . . . . .
H182 H 1.0706 0.4305 -0.0827 0.0548 1.0000 Uiso R . . . . .
H183 H 1.0180 0.3417 -0.1511 0.0549 1.0000 Uiso R . . . . .
H61 H 0.5645 0.3159 0.3530 0.0401 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.043(3) 0.0419(12) 0.033(2) 0.0047(12) 0.009(2) 0.0046(14)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.62(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . C2 . 1.729(11) yes
S1 . C5 . 1.722(10) yes
C2 . C3 . 1.349(14) yes
C2 . C18 . 1.511(10) yes
C3 . C4 . 1.445(10) yes
C3 . H31 . 0.923 no
C4 . C5 . 1.345(14) yes
C4 . C16 . 1.427(13) yes
C5 . N6 . 1.415(11) yes
C7 . C8 . 1.403(15) yes
C7 . C12 . 1.411(11) yes
C7 . N6 . 1.382(11) yes
C8 . C9 . 1.370(12) yes
C8 . H81 . 0.924 no
C9 . C10 . 1.386(12) yes
C9 . H91 . 0.936 no
C10 . C11 . 1.349(16) yes
C10 . H101 . 0.934 no
C11 . C12 . 1.395(12) yes
C11 . H111 . 0.930 no
C12 . N13 . 1.451(15) yes
C16 . N17 . 1.135(12) yes
C18 . H181 . 0.959 no
C18 . H182 . 0.957 no
C18 . H183 . 0.962 no
N6 . H61 . 0.849 no
N13 . O14 . 1.245(10) yes
N13 . O15 . 1.211(10) yes
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
C2 . S1 . C5 . 91.6(5) yes
S1 . C2 . C3 . 112.1(6) yes
S1 . C2 . C18 . 119.3(10) yes
C3 . C2 . C18 . 128.6(10) yes
C2 . C3 . C4 . 111.5(10) yes
C2 . C3 . H31 . 124.8 no
C4 . C3 . H31 . 123.8 no
C3 . C4 . C5 . 113.5(9) yes
C3 . C4 . C16 . 124.1(11) yes
C5 . C4 . C16 . 122.4(8) yes
S1 . C5 . C4 . 111.3(6) yes
S1 . C5 . N6 . 119.9(9) yes
C4 . C5 . N6 . 128.7(9) yes
C8 . C7 . C12 . 115.3(9) yes
C8 . C7 . N6 . 121.5(9) yes
C12 . C7 . N6 . 123.3(11) yes
C7 . C8 . C9 . 122.4(10) yes
C7 . C8 . H81 . 119.3 no
C9 . C8 . H81 . 118.3 no
C8 . C9 . C10 . 119.6(13) yes
C8 . C9 . H91 . 119.6 no
C10 . C9 . H91 . 120.9 no
C9 . C10 . C11 . 121.3(11) yes
C9 . C10 . H101 . 119.2 no
C11 . C10 . H101 . 119.6 no
C10 . C11 . C12 . 118.9(10) yes
C10 . C11 . H111 . 121.1 no
C12 . C11 . H111 . 120.0 no
C7 . C12 . C11 . 122.6(11) yes
C7 . C12 . N13 . 120.8(9) yes
C11 . C12 . N13 . 116.5(9) yes
C4 . C16 . N17 . 174.6(15) yes
C2 . C18 . H181 . 108.3 no
C2 . C18 . H182 . 109.9 no
H181 . C18 . H182 . 110.1 no
C2 . C18 . H183 . 109.0 no
H181 . C18 . H183 . 109.2 no
H182 . C18 . H183 . 110.5 no
C5 . N6 . C7 . 121.9(10) yes
C5 . N6 . H61 . 119.1 no
C7 . N6 . H61 . 119.0 no
C12 . N13 . O14 . 118.6(9) yes
C12 . N13 . O15 . 120.3(8) yes
O14 . N13 . O15 . 121.1(11) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 16/12/14 at 13:32:35
#
#Refinement with riding constraints on H atoms
#LIST     12                                                                    
BLOCK SCALE X'S, 
CONT S(1,U'S) 
CONT C(2,U[ISO]) UNTIL O(15) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  18,X'S) H   ( 183,X'S) H   ( 182,X'S) H   ( 181,X'S) 
RIDE N   (   6,X'S) H   (  61,X'S) 
END

#Refinement of hydrogen positions and U[iso] with restraints
#LIST 12
block
CONT H(   31 ,X,Y,Z,U[ISO])
CONT H(   81 ,X,Y,Z,U[ISO])
CONT H(   91 ,X,Y,Z,U[ISO])
CONT H(  101 ,X,Y,Z,U[ISO])
CONT H(  111 ,X,Y,Z,U[ISO])
CONT H(  183 ,X,Y,Z,U[ISO])
CONT H(  182 ,X,Y,Z,U[ISO])
CONT H(  181 ,X,Y,Z,U[ISO])
CONT H(   61 ,X,Y,Z,U[ISO])
END
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 16/12/14 at 13:32:35
#
#Non-H atom restraints
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
REM   DELU   START (DO NOT REMOVE THIS LINE) 
VIBR .0, 0.00200 = S(1) TO C(2) 
VIBR .0, 0.00200 = S(1) TO C(5) 
VIBR .0, 0.00500 = C(5) TO C(2) 
VIBR .0, 0.00200 = C(2) TO C(18) 
VIBR .0, 0.00200 = C(2) TO C(3) 
VIBR .0, 0.00500 = C(18) TO S(1) 
VIBR .0, 0.00500 = C(3) TO S(1) 
VIBR .0, 0.00500 = C(3) TO C(18) 
VIBR .0, 0.00200 = C(3) TO C(4) 
VIBR .0, 0.00500 = C(4) TO C(2) 
VIBR .0, 0.00200 = C(4) TO C(5) 
VIBR .0, 0.00200 = C(4) TO C(16) 
VIBR .0, 0.00500 = C(5) TO C(3) 
VIBR .0, 0.00500 = C(16) TO C(3) 
VIBR .0, 0.00500 = C(16) TO C(5) 
VIBR .0, 0.00200 = C(5) TO N(6) 
VIBR .0, 0.00500 = S(1) TO C(4) 
VIBR .0, 0.00500 = N(6) TO C(4) 
VIBR .0, 0.00500 = N(6) TO S(1) 
VIBR .0, 0.00200 = N(6) TO C(7) 
VIBR .0, 0.00500 = C(7) TO C(5) 
VIBR .0, 0.00200 = C(7) TO C(8) 
VIBR .0, 0.00200 = C(7) TO C(12) 
VIBR .0, 0.00500 = C(8) TO N(6) 
VIBR .0, 0.00500 = C(12) TO N(6) 
VIBR .0, 0.00500 = C(12) TO C(8) 
VIBR .0, 0.00200 = C(8) TO C(9) 
VIBR .0, 0.00500 = C(9) TO C(7) 
VIBR .0, 0.00200 = C(9) TO C(10) 
VIBR .0, 0.00500 = C(10) TO C(8) 
VIBR .0, 0.00200 = C(10) TO C(11) 
VIBR .0, 0.00500 = C(11) TO C(9) 
VIBR .0, 0.00200 = C(11) TO C(12) 
VIBR .0, 0.00500 = C(12) TO C(10) 
VIBR .0, 0.00200 = C(12) TO N(13) 
VIBR .0, 0.00500 = C(7) TO C(11) 
VIBR .0, 0.00500 = N(13) TO C(11) 
VIBR .0, 0.00500 = N(13) TO C(7) 
VIBR .0, 0.00200 = N(13) TO O(14) 
VIBR .0, 0.00200 = N(13) TO O(15) 
VIBR .0, 0.00500 = O(14) TO C(12) 
VIBR .0, 0.00500 = O(15) TO C(12) 
VIBR .0, 0.00500 = O(15) TO O(14) 
VIBR .0, 0.00200 = C(16) TO N(17) 
VIBR .0, 0.00500 = N(17) TO C(4) 
REM   DELU   END (DO NOT REMOVE THIS LINE) 
REM   THERMSIM   START (DO NOT REMOVE THIS LINE) 
U(IJ) .0, 0.04000 = S(1) TO C(2) 
U(IJ) .0, 0.04000 = S(1) TO C(5) 
U(IJ) .0, 0.08000 = C(2) TO C(18) 
U(IJ) .0, 0.04000 = C(2) TO C(3) 
U(IJ) .0, 0.04000 = C(3) TO C(4) 
U(IJ) .0, 0.04000 = C(4) TO C(5) 
U(IJ) .0, 0.04000 = C(4) TO C(16) 
U(IJ) .0, 0.04000 = C(5) TO N(6) 
U(IJ) .0, 0.04000 = N(6) TO C(7) 
U(IJ) .0, 0.04000 = C(7) TO C(8) 
U(IJ) .0, 0.04000 = C(7) TO C(12) 
U(IJ) .0, 0.04000 = C(8) TO C(9) 
U(IJ) .0, 0.04000 = C(9) TO C(10) 
U(IJ) .0, 0.04000 = C(10) TO C(11) 
U(IJ) .0, 0.04000 = C(11) TO C(12) 
U(IJ) .0, 0.04000 = C(12) TO N(13) 
U(IJ) .0, 0.08000 = N(13) TO O(14) 
U(IJ) .0, 0.08000 = N(13) TO O(15) 
U(IJ) .0, 0.08000 = C(16) TO N(17) 
REM   THERMSIM   END (DO NOT REMOVE THIS LINE) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
DISTANCE 1.220000 , 0.020000 = N(13) TO O(14) 
DISTANCE 1.220000 , 0.020000 = N(13) TO O(15) 
DISTANCE 1.450000 , 0.020000 = C(12) TO N(13) 
DISTANCE 1.390000 , 0.020000 = C(11) TO C(12) 
DISTANCE 1.360000 , 0.020000 = C(10) TO C(11) 
DISTANCE 1.390000 , 0.020000 = C(9) TO C(10) 
DISTANCE 1.370000 , 0.020000 = C(8) TO C(9) 
DISTANCE 1.400000 , 0.020000 = C(7) TO C(8) 
DISTANCE 1.410000 , 0.020000 = C(7) TO C(12) 
DISTANCE 1.370000 , 0.020000 = C(7) TO N(6) 
DISTANCE 1.400000 , 0.02000 = C(5) TO N(6) 
DISTANCE 1.720000 , 0.020000 = S(1) TO C(5) 
DISTANCE 1.720000 , 0.020000 = S(1) TO C(2) 
DISTANCE 1.350000 , 0.020000 = C(2) TO C(3) 
DISTANCE 1.430000 , 0.020000 = C(3) TO C(4) 
DISTANCE 1.360000 , 0.020000 = C(4) TO C(5) 
DISTANCE 1.430000 , 0.020000 = C(4) TO C(16) 
DISTANCE 1.140000 , 0.020000 = C(16) TO N(17) 
DISTANCE 1.500000 , 0.020000 = C(2) TO C(18) 
END          

#Restraints used for hydrogen refinement
#LIST 16
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 3) to H(31) 
REST 0.042, 0.002 = H(31,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(31) TO C ( 3) TO C(2) 
CONT H(31) TO C ( 3) TO C(4) 
PLANAR C ( 3) C(2) C(4) H(31) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 8) to H(81) 
REST 0.048, 0.002 = H(81,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(81) TO C ( 8) TO C(7) 
CONT H(81) TO C ( 8) TO C(9) 
PLANAR C ( 8) C(7) C(9) H(81) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 9) to H(91) 
REST 0.052, 0.002 = H(91,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(91) TO C ( 9) TO C(8) 
CONT H(91) TO C ( 9) TO C(10) 
PLANAR C ( 9) C(8) C(10) H(91) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 10) to H(101) 
REST 0.051, 0.002 = H(101,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(101) TO C ( 10) TO C(9) 
CONT H(101) TO C ( 10) TO C(11) 
PLANAR C ( 10) C(9) C(11) H(101) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 11) to H(111) 
REST 0.049, 0.002 = H(111,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(111) TO C ( 11) TO C(10) 
CONT H(111) TO C ( 11) TO C(12) 
PLANAR C ( 11) C(10) C(12) H(111) 
REM            3 H on sp 3
DIST 0.96, 0.02 = 
CONT C ( 18) to H(183) 
CONT C ( 18) to H(182) 
CONT C ( 18) to H(181) 
REST 0.055, 0.002 = H(183,U[ISO]) 
REST 0.055, 0.002 = H(182,U[ISO]) 
REST 0.055, 0.002 = H(181,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(2) to C ( 18) to H(183) 
CONT C(2) to C ( 18) to H(182) 
CONT C(2) to C ( 18) to H(181) 
ANGLE 0.0, 2.0 = mean H(183) to C ( 18) to H(182) 
CONT H(183) to C ( 18) to H(181) 
CONT H(182) to C ( 18) to H(181) 
REM            H1-N-R2
DIST 0.86, 0.02 = 
CONT N ( 6) to H(61) 
REST 0.040, 0.002 = H(61,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(61) TO N ( 6) TO C(5) 
CONT H(61) TO N ( 6) TO C(7) 
PLANAR 0.010000  C(5) C(7) N(6) H(61) 
END
;
_chemical_name_common            ROY
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_Y_0.99_GPa
_database_code_depnum_ccdc_archive 'CCDC 1058324'
_audit_update_record             
;
2015-04-07 deposited with the CCDC.
2015-05-20 downloaded from the CCDC.
;
_audit_creation_date             14-12-16
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'ROY Y-form, 0.99 GPa'
_chemical_name_systematic        
5-methyl-2-((2-nitrophenyl)amino)-3-thiophenecarbonitrile


_exptl_special_details           
; 
The crystal was loaded in a Merrill-Bassett diamond anvil cell, using 4:1 
methanol:ethanol as a pressure-transmitting medium and ruby as a pressure 
marker. Pressure was measured before and after data collection and the average
of these - 0.99 GPa - was taken to be the experimental pressure.
;


_refine_special_details          
; 
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      18.52 Degree
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......      0.508 Note  
PLAT340_ALERT_3_B Low Bond Precision on  C-C Bonds ...............     0.0141 Ang.  
PLAT911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L=  0.588        823 Report
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5879
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large.       8.55 Why ? 
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          49 %     
PLAT950_ALERT_5_G Calculated (ThMax) and CIF-Reported Kmax Differ           2 Units 
PLAT956_ALERT_1_G Calculated (ThMax) and Actual (FCF) Hmax Differ           2 Units 
PLAT960_ALERT_3_G Number of Intensities with I  <   - 2*sig(I) ...          3 Check  

Much of reciprocal space is unmeasurable, owing to the body of the diamond 
anvil cell, leading to missing reflections, low completeness and poor statistics.
Data are 47.8% complete to 0.85 Angstroms. Resolution and completeness 
statistics are given below.

#===================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#===================================================
Theta sin(th)/Lambda Complete  Expected Measured  Missing
#-------------------------------------------------------------------------------
 20.82     0.500     0.522         1108      578      530
 23.01     0.550     0.517         1434      742      692
 24.70     0.588     0.514         1693      870      823
------------------------------------------------------------ ACTA Min. Res. ---


PLAT921_ALERT_1_B R1  in the CIF and FCF Differ by ...............    -0.0172 Check 
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......    149.768 Check 
PLAT926_ALERT_1_C Reported and Calculated   R1 Differ by .........     0.0022 Check 

Crystals labels omitted reflections with several different flags that describe 
the reason for their omission. PLATON does not recognise this format and 
these omitted reflections have been included in the calculation of R1 and K.


PLAT201_ALERT_2_A Isotropic non-H Atoms in Main Residue(s) .......         17 Report
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         18 Note  
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         18 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         64 Note  

Owing to poor data quality, only the relatively electron-rich sulfur atom could be 
refined anisotropically. Distance, vibration and thermal similarity restraints were 
necessary for a stable refinement. Previous variable-pressure experiments on 
organic materials have shown that pressure has little effect on covalent bond 
lengths and so the model has been restrained to the values observed at ambient 
pressure. The refinement procedure is discussed above and the restraints used 
are given at the end of this file.


PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !

These are given further below.


PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check 
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check 

This is correct.


PLAT432_ALERT_2_G Short Inter X...Y Contact  O14    ..  C18     ..       2.92 Ang.  

Short contacts are not unusual for high-pressure structures.
;

_cell_length_a                   8.2031(15)
_cell_length_b                   15.4235(10)
_cell_length_c                   8.4569(14)
_cell_angle_alpha                90
_cell_angle_beta                 90.851(14)
_cell_angle_gamma                90
_cell_volume                     1069.9(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-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 = C9 H6.75 N2.25 O1.50 S0.75 
# Dc =      1.21 Fooo =    536.00 Mu =      2.24 M =    194.47
# Found Formula = C12 H9 N3 O2 S1 
# Dc =      1.61 FOOO =    536.00 Mu =      2.99 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    1996
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25
_cell_measurement_temperature    293

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.097
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_max          0.165

_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.299

# Sheldrick geometric approximatio 0.97 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.97
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ


_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'User-defined model'
_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         0.99 #GPa
_diffrn_reflns_number            6483
_reflns_number_total             870
_diffrn_reflns_av_R_equivalents  0.069
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 870 
# Theoretical number of reflections is about 3642 


_diffrn_reflns_theta_min         2.641
_diffrn_reflns_theta_max         24.697
_diffrn_measured_fraction_theta_max 0.478

_diffrn_reflns_theta_full        18.523
_diffrn_measured_fraction_theta_full 0.508


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_reflns_limit_h_min              -7
_reflns_limit_h_max              5
_reflns_limit_k_min              0
_reflns_limit_k_max              18
_reflns_limit_l_min              0
_reflns_limit_l_max              9

_oxford_diffrn_Wilson_B_factor   1.97
_oxford_diffrn_Wilson_scale      0.22

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

_refine_diff_density_min         -0.65
_refine_diff_density_max         0.69


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>0.0\s(I)
_refine_ls_number_reflns         862
_refine_ls_number_restraints     64
_refine_ls_number_parameters     78
_oxford_refine_ls_R_factor_ref   0.1065
_refine_ls_wR_factor_ref         0.1526
_refine_ls_goodness_of_fit_ref   0.9879
_refine_ls_shift/su_max          0.0000769
_refine_ls_shift/su_mean         0.0000122


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        864
_refine_ls_R_factor_all          0.1067
_refine_ls_wR_factor_all         0.1533

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                651
_refine_ls_R_factor_gt           0.0800
_refine_ls_wR_factor_gt          0.1384

_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.00P)² + 8.55P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

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


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 0.8014(4) 0.38526(12) 0.1115(3) 0.0317 1.0000 Uani D U . . . .
C2 C 0.9978(13) 0.3482(4) 0.0849(12) 0.0289(12) 1.0000 Uiso D U . . . .
C3 C 1.0547(14) 0.3026(4) 0.2103(11) 0.0286(12) 1.0000 Uiso D U . . . .
C4 C 0.9341(13) 0.2975(4) 0.3308(11) 0.0282(11) 1.0000 Uiso D U . . . .
C5 C 0.7949(13) 0.3389(4) 0.2959(11) 0.0263(11) 1.0000 Uiso D U . . . .
C7 C 0.6432(13) 0.3934(4) 0.5223(11) 0.0293(11) 1.0000 Uiso D U . . . .
C8 C 0.7815(14) 0.4347(4) 0.5858(12) 0.0327(13) 1.0000 Uiso D U . . . .
C9 C 0.7735(15) 0.4864(5) 0.7187(13) 0.0361(13) 1.0000 Uiso D U . . . .
C10 C 0.6264(14) 0.4971(5) 0.7949(13) 0.0355(13) 1.0000 Uiso D U . . . .
C11 C 0.4908(15) 0.4568(4) 0.7410(12) 0.0327(13) 1.0000 Uiso D U . . . .
C12 C 0.4968(14) 0.4053(4) 0.6064(12) 0.0321(11) 1.0000 Uiso D U . . . .
C16 C 0.9566(15) 0.2530(4) 0.4779(12) 0.0324(13) 1.0000 Uiso D U . . . .
C18 C 1.0806(16) 0.3674(4) -0.0695(13) 0.0293(14) 1.0000 Uiso D U . . . .
N6 N 0.6510(12) 0.3450(3) 0.3848(10) 0.0275(11) 1.0000 Uiso D U . . . .
N13 N 0.3453(12) 0.3691(4) 0.5487(11) 0.0363(11) 1.0000 Uiso D U . . . .
N17 N 0.9677(14) 0.2173(4) 0.5962(11) 0.0391(15) 1.0000 Uiso D U . . . .
O14 O 0.2190(11) 0.3907(3) 0.6170(10) 0.0448(13) 1.0000 Uiso D U . . . .
O15 O 0.3444(12) 0.3183(3) 0.4390(10) 0.0418(13) 1.0000 Uiso D U . . . .
H31 H 1.1577 0.2786 0.2179 0.0339 1.0000 Uiso R . . . . .
H81 H 0.8809 0.4277 0.5379 0.0389 1.0000 Uiso R . . . . .
H91 H 0.8681 0.5139 0.7555 0.0433 1.0000 Uiso R . . . . .
H101 H 0.6208 0.5326 0.8849 0.0434 1.0000 Uiso R . . . . .
H111 H 0.3929 0.4625 0.7935 0.0391 1.0000 Uiso R . . . . .
H181 H 1.1885 0.3441 -0.0645 0.0440 1.0000 Uiso R . . . . .
H182 H 1.0853 0.4287 -0.0865 0.0438 1.0000 Uiso R . . . . .
H183 H 1.0206 0.3399 -0.1540 0.0440 1.0000 Uiso R . . . . .
H61 H 0.5660 0.3185 0.3523 0.0332 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.036(2) 0.0337(9) 0.0258(18) 0.0038(10) 0.005(2) 0.0042(11)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          2.00(4)
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 . C2 . 1.727(10) yes
S1 . C5 . 1.717(9) yes
C2 . C3 . 1.350(13) yes
C2 . C18 . 1.510(9) yes
C3 . C4 . 1.433(9) yes
C3 . H31 . 0.924 no
C4 . C5 . 1.337(13) yes
C4 . C16 . 1.430(12) yes
C5 . N6 . 1.412(9) yes
C7 . C8 . 1.401(14) yes
C7 . C12 . 1.417(10) yes
C7 . N6 . 1.384(10) yes
C8 . C9 . 1.380(11) yes
C8 . H81 . 0.922 no
C9 . C10 . 1.387(11) yes
C9 . H91 . 0.933 no
C10 . C11 . 1.348(15) yes
C10 . H101 . 0.939 no
C11 . C12 . 1.390(11) yes
C11 . H111 . 0.928 no
C12 . N13 . 1.441(14) yes
C16 . N17 . 1.145(11) yes
C18 . H181 . 0.956 no
C18 . H182 . 0.957 no
C18 . H183 . 0.961 no
N6 . H61 . 0.851 no
N13 . O14 . 1.240(8) yes
N13 . O15 . 1.214(9) yes
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
C2 . S1 . C5 . 91.2(5) yes
S1 . C2 . C3 . 112.5(5) yes
S1 . C2 . C18 . 118.7(8) yes
C3 . C2 . C18 . 128.8(9) yes
C2 . C3 . C4 . 110.7(9) yes
C2 . C3 . H31 . 124.7 no
C4 . C3 . H31 . 124.7 no
C3 . C4 . C5 . 114.4(8) yes
C3 . C4 . C16 . 124.3(9) yes
C5 . C4 . C16 . 121.4(7) yes
S1 . C5 . C4 . 111.2(5) yes
S1 . C5 . N6 . 119.5(8) yes
C4 . C5 . N6 . 129.2(8) yes
C8 . C7 . C12 . 115.8(8) yes
C8 . C7 . N6 . 121.4(7) yes
C12 . C7 . N6 . 122.8(10) yes
C7 . C8 . C9 . 121.8(8) yes
C7 . C8 . H81 . 119.6 no
C9 . C8 . H81 . 118.6 no
C8 . C9 . C10 . 120.0(11) yes
C8 . C9 . H91 . 119.0 no
C10 . C9 . H91 . 121.1 no
C9 . C10 . C11 . 120.5(9) yes
C9 . C10 . H101 . 120.0 no
C11 . C10 . H101 . 119.6 no
C10 . C11 . C12 . 120.1(9) yes
C10 . C11 . H111 . 120.6 no
C12 . C11 . H111 . 119.2 no
C7 . C12 . C11 . 121.7(10) yes
C7 . C12 . N13 . 120.9(8) yes
C11 . C12 . N13 . 117.3(8) yes
C4 . C16 . N17 . 177.1(12) yes
C2 . C18 . H181 . 108.4 no
C2 . C18 . H182 . 110.1 no
H181 . C18 . H182 . 109.8 no
C2 . C18 . H183 . 108.9 no
H181 . C18 . H183 . 109.3 no
H182 . C18 . H183 . 110.3 no
C5 . N6 . C7 . 122.2(9) yes
C5 . N6 . H61 . 118.9 no
C7 . N6 . H61 . 118.9 no
C12 . N13 . O14 . 117.4(8) yes
C12 . N13 . O15 . 120.3(7) yes
O14 . N13 . O15 . 122.3(10) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 16/12/14 at 13:36:11
#
#Refinement with riding constraints on H atoms
#LIST     12                                                                    
BLOCK SCALE X'S, 
CONT S(1,U'S) 
CONT C(2,U[ISO]) UNTIL O(15) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  18,X'S) H   ( 183,X'S) H   ( 182,X'S) H   ( 181,X'S) 
RIDE N   (   6,X'S) H   (  61,X'S) 
END          

#Refinement of hydrogen positions and U[iso] with restraints
#LIST 12
block
CONT H(   31 ,X,Y,Z,U[ISO])
CONT H(   81 ,X,Y,Z,U[ISO])
CONT H(   91 ,X,Y,Z,U[ISO])
CONT H(  101 ,X,Y,Z,U[ISO])
CONT H(  111 ,X,Y,Z,U[ISO])
CONT H(  183 ,X,Y,Z,U[ISO])
CONT H(  182 ,X,Y,Z,U[ISO])
CONT H(  181 ,X,Y,Z,U[ISO])
CONT H(   61 ,X,Y,Z,U[ISO])
END
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 16/12/14 at 13:36:11
#
#Non-H atom restraints
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
REM   DELU   START (DO NOT REMOVE THIS LINE) 
VIBR .0, 0.00200 = S(1) TO C(2) 
VIBR .0, 0.00200 = S(1) TO C(5) 
VIBR .0, 0.00500 = C(5) TO C(2) 
VIBR .0, 0.00200 = C(2) TO C(18) 
VIBR .0, 0.00200 = C(2) TO C(3) 
VIBR .0, 0.00500 = C(18) TO S(1) 
VIBR .0, 0.00500 = C(3) TO S(1) 
VIBR .0, 0.00500 = C(3) TO C(18) 
VIBR .0, 0.00200 = C(3) TO C(4) 
VIBR .0, 0.00500 = C(4) TO C(2) 
VIBR .0, 0.00200 = C(4) TO C(5) 
VIBR .0, 0.00200 = C(4) TO C(16) 
VIBR .0, 0.00500 = C(5) TO C(3) 
VIBR .0, 0.00500 = C(16) TO C(3) 
VIBR .0, 0.00500 = C(16) TO C(5) 
VIBR .0, 0.00200 = C(5) TO N(6) 
VIBR .0, 0.00500 = S(1) TO C(4) 
VIBR .0, 0.00500 = N(6) TO C(4) 
VIBR .0, 0.00500 = N(6) TO S(1) 
VIBR .0, 0.00200 = N(6) TO C(7) 
VIBR .0, 0.00500 = C(7) TO C(5) 
VIBR .0, 0.00200 = C(7) TO C(8) 
VIBR .0, 0.00200 = C(7) TO C(12) 
VIBR .0, 0.00500 = C(8) TO N(6) 
VIBR .0, 0.00500 = C(12) TO N(6) 
VIBR .0, 0.00500 = C(12) TO C(8) 
VIBR .0, 0.00200 = C(8) TO C(9) 
VIBR .0, 0.00500 = C(9) TO C(7) 
VIBR .0, 0.00200 = C(9) TO C(10) 
VIBR .0, 0.00500 = C(10) TO C(8) 
VIBR .0, 0.00200 = C(10) TO C(11) 
VIBR .0, 0.00500 = C(11) TO C(9) 
VIBR .0, 0.00200 = C(11) TO C(12) 
VIBR .0, 0.00500 = C(12) TO C(10) 
VIBR .0, 0.00200 = C(12) TO N(13) 
VIBR .0, 0.00500 = C(7) TO C(11) 
VIBR .0, 0.00500 = N(13) TO C(11) 
VIBR .0, 0.00500 = N(13) TO C(7) 
VIBR .0, 0.00200 = N(13) TO O(14) 
VIBR .0, 0.00200 = N(13) TO O(15) 
VIBR .0, 0.00500 = O(14) TO C(12) 
VIBR .0, 0.00500 = O(15) TO C(12) 
VIBR .0, 0.00500 = O(15) TO O(14) 
VIBR .0, 0.00200 = C(16) TO N(17) 
VIBR .0, 0.00500 = N(17) TO C(4) 
REM   DELU   END (DO NOT REMOVE THIS LINE) 
REM   THERMSIM   START (DO NOT REMOVE THIS LINE) 
U(IJ) .0, 0.04000 = S(1) TO C(2) 
U(IJ) .0, 0.04000 = S(1) TO C(5) 
U(IJ) .0, 0.08000 = C(2) TO C(18) 
U(IJ) .0, 0.04000 = C(2) TO C(3) 
U(IJ) .0, 0.04000 = C(3) TO C(4) 
U(IJ) .0, 0.04000 = C(4) TO C(5) 
U(IJ) .0, 0.04000 = C(4) TO C(16) 
U(IJ) .0, 0.04000 = C(5) TO N(6) 
U(IJ) .0, 0.04000 = N(6) TO C(7) 
U(IJ) .0, 0.04000 = C(7) TO C(8) 
U(IJ) .0, 0.04000 = C(7) TO C(12) 
U(IJ) .0, 0.04000 = C(8) TO C(9) 
U(IJ) .0, 0.04000 = C(9) TO C(10) 
U(IJ) .0, 0.04000 = C(10) TO C(11) 
U(IJ) .0, 0.04000 = C(11) TO C(12) 
U(IJ) .0, 0.04000 = C(12) TO N(13) 
U(IJ) .0, 0.08000 = N(13) TO O(14) 
U(IJ) .0, 0.08000 = N(13) TO O(15) 
U(IJ) .0, 0.08000 = C(16) TO N(17) 
REM   THERMSIM   END (DO NOT REMOVE THIS LINE) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
DISTANCE 1.220000 , 0.020000 = N(13) TO O(14) 
DISTANCE 1.220000 , 0.020000 = N(13) TO O(15) 
DISTANCE 1.450000 , 0.020000 = C(12) TO N(13) 
DISTANCE 1.390000 , 0.020000 = C(11) TO C(12) 
DISTANCE 1.360000 , 0.020000 = C(10) TO C(11) 
DISTANCE 1.390000 , 0.020000 = C(9) TO C(10) 
DISTANCE 1.370000 , 0.020000 = C(8) TO C(9) 
DISTANCE 1.400000 , 0.020000 = C(7) TO C(8) 
DISTANCE 1.410000 , 0.020000 = C(7) TO C(12) 
DISTANCE 1.370000 , 0.020000 = C(7) TO N(6) 
DISTANCE 1.400000 , 0.02000 = C(5) TO N(6) 
DISTANCE 1.720000 , 0.020000 = S(1) TO C(5) 
DISTANCE 1.720000 , 0.020000 = S(1) TO C(2) 
DISTANCE 1.350000 , 0.020000 = C(2) TO C(3) 
DISTANCE 1.430000 , 0.020000 = C(3) TO C(4) 
DISTANCE 1.360000 , 0.020000 = C(4) TO C(5) 
DISTANCE 1.430000 , 0.020000 = C(4) TO C(16) 
DISTANCE 1.140000 , 0.020000 = C(16) TO N(17) 
DISTANCE 1.500000 , 0.020000 = C(2) TO C(18) 
END          

#Restraints used for hydrogen refinement
#LIST 16
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 3) to H(31) 
REST 0.034, 0.002 = H(31,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(31) TO C ( 3) TO C(2) 
CONT H(31) TO C ( 3) TO C(4) 
PLANAR C ( 3) C(2) C(4) H(31) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 8) to H(81) 
REST 0.039, 0.002 = H(81,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(81) TO C ( 8) TO C(7) 
CONT H(81) TO C ( 8) TO C(9) 
PLANAR C ( 8) C(7) C(9) H(81) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 9) to H(91) 
REST 0.043, 0.002 = H(91,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(91) TO C ( 9) TO C(8) 
CONT H(91) TO C ( 9) TO C(10) 
PLANAR C ( 9) C(8) C(10) H(91) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 10) to H(101) 
REST 0.043, 0.002 = H(101,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(101) TO C ( 10) TO C(9) 
CONT H(101) TO C ( 10) TO C(11) 
PLANAR C ( 10) C(9) C(11) H(101) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 11) to H(111) 
REST 0.039, 0.002 = H(111,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(111) TO C ( 11) TO C(10) 
CONT H(111) TO C ( 11) TO C(12) 
PLANAR C ( 11) C(10) C(12) H(111) 
REM            3 H on sp 3
DIST 0.96, 0.02 = 
CONT C ( 18) to H(183) 
CONT C ( 18) to H(182) 
CONT C ( 18) to H(181) 
REST 0.044, 0.002 = H(183,U[ISO]) 
REST 0.044, 0.002 = H(182,U[ISO]) 
REST 0.044, 0.002 = H(181,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(2) to C ( 18) to H(183) 
CONT C(2) to C ( 18) to H(182) 
CONT C(2) to C ( 18) to H(181) 
ANGLE 0.0, 2.0 = mean H(183) to C ( 18) to H(182) 
CONT H(183) to C ( 18) to H(181) 
CONT H(182) to C ( 18) to H(181) 
REM            H1-N-R2
DIST 0.86, 0.02 = 
CONT N ( 6) to H(61) 
REST 0.033, 0.002 = H(61,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(61) TO N ( 6) TO C(5) 
CONT H(61) TO N ( 6) TO C(7) 
PLANAR 0.010000  C(5) C(7) N(6) H(61) 
END
;
_chemical_name_common            ROY
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_Y_1.49_GPa
_database_code_depnum_ccdc_archive 'CCDC 1058325'
_audit_update_record             
;
2015-04-07 deposited with the CCDC.
2015-05-20 downloaded from the CCDC.
;
_audit_creation_date             14-12-16
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'ROY_Y-form, 1.49 GPa'
_chemical_name_systematic        
5-methyl-2-((2-nitrophenyl)amino)-3-thiophenecarbonitrile


_exptl_special_details           
; 
The crystal was loaded in a Merrill-Bassett diamond anvil cell, using 4:1 
methanol:ethanol as a pressure-transmitting medium and ruby as a pressure 
marker. Pressure was measured before and after data collection and the average
of these - 1.49 GPa - was taken to be the experimental pressure.
;


_refine_special_details          
; 
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      18.51 Degree
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......      0.517 Note  
PLAT340_ALERT_3_B Low Bond Precision on  C-C Bonds ...............     0.0135 Ang.  
PLAT911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L=  0.588        787 Report
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5876
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large.       8.61 Why ? 
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          60 %     
PLAT950_ALERT_5_G Calculated (ThMax) and CIF-Reported Kmax Differ           2 Units 
PLAT956_ALERT_1_G Calculated (ThMax) and Actual (FCF) Hmax Differ           2 Units 
PLAT960_ALERT_3_G Number of Intensities with I  <   - 2*sig(I) ...          6 Check 

Much of reciprocal space is unmeasurable, owing to the body of the diamond 
anvil cell, leading to missing reflections, low completeness and poor statistics.
Data are 49.1% complete to 0.85 Angstroms. Resolution and completeness 
statistics are given below.

#====================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#====================================================
Theta sin(th)/Lambda Complete  Expected Measured  Missing
#-------------------------------------------------------------------------------
 20.82     0.500     0.535         1085      580      505
 23.01     0.550     0.527         1394      734      660
 24.69     0.588     0.524         1654      867      787
------------------------------------------------------------ ACTA Min. Res. ---


PLAT921_ALERT_1_B R1  in the CIF and FCF Differ by ...............    -0.0170 Check 
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......    165.578 Check 

Crystals labels omitted reflections with several different flags that describe 
the reason for their omission. PLATON does not recognise this format and 
these omitted reflections have been included in the calculation of R1 and K.


PLAT201_ALERT_2_A Isotropic non-H Atoms in Main Residue(s) .......         17 Report
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         18 Note  
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         18 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         64 Note  

Owing to poor data quality, only the relatively electron-rich sulfur atom could be 
refined anisotropically. Distance, vibration and thermal similarity restraints were 
necessary for a stable refinement. Previous variable-pressure experiments on 
organic materials have shown that pressure has little effect on covalent bond 
lengths and so the model has been restrained to the values observed at ambient 
pressure. The refinement procedure is discussed above and the restraints used 
are given at the end of this file.


PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do ! 

These are given further below.

PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check 
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check

This is correct


PLAT432_ALERT_2_G Short Inter X...Y Contact  O14    ..  C18     ..       2.89 Ang.  
PLAT432_ALERT_2_G Short Inter X...Y Contact  O15    ..  C3      ..       3.01 Ang.  

Short contacts are not unusual for high-pressure structures.
;


_cell_length_a                   8.116(2)
_cell_length_b                   15.1210(10)
_cell_length_c                   8.4699(16)
_cell_angle_alpha                90
_cell_angle_beta                 90.38(3)
_cell_angle_gamma                90
_cell_volume                     1039.4(4)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-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 = C9 H6.75 N2.25 O1.50 S0.75 
# Dc =      1.24 Fooo =    536.00 Mu =      2.31 M =    194.47
# Found Formula = C12 H9 N3 O2 S1 
# Dc =      1.66 FOOO =    536.00 Mu =      3.08 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    2047
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25
_cell_measurement_temperature    293

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.097
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_max          0.165

_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.308

# Sheldrick geometric approximatio 0.97 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.21
_exptl_absorpt_correction_T_max  0.97
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ


_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'User-defined model'
_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         1.49 #GPa
_diffrn_reflns_number            6322
_reflns_number_total             867
_diffrn_reflns_av_R_equivalents  0.058
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 867 
# Theoretical number of reflections is about 3534 


_diffrn_reflns_theta_min         2.694
_diffrn_reflns_theta_max         24.686
_diffrn_measured_fraction_theta_max 0.491

_diffrn_reflns_theta_full        18.515
_diffrn_measured_fraction_theta_full 0.517


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_reflns_limit_h_min              -7
_reflns_limit_h_max              5
_reflns_limit_k_min              0
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              9

_oxford_diffrn_Wilson_B_factor   1.63
_oxford_diffrn_Wilson_scale      0.20

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

_refine_diff_density_min         -0.75
_refine_diff_density_max         0.78


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         861
_refine_ls_number_restraints     64
_refine_ls_number_parameters     78
_oxford_refine_ls_R_factor_ref   0.0980
_refine_ls_wR_factor_ref         0.1667
_refine_ls_goodness_of_fit_ref   0.9781
_refine_ls_shift/su_max          0.0000803
_refine_ls_shift/su_mean         0.0000110


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        861
_refine_ls_R_factor_all          0.0980
_refine_ls_wR_factor_all         0.1667

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                654
_refine_ls_R_factor_gt           0.0759
_refine_ls_wR_factor_gt          0.1524

_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.03P)² + 8.61P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

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


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 0.8094(4) 0.38422(11) 0.1110(3) 0.0304 1.0000 Uani D U . . . .
C2 C 1.0074(13) 0.3457(4) 0.0823(11) 0.0274(12) 1.0000 Uiso D U . . . .
C3 C 1.0628(14) 0.3009(4) 0.2083(11) 0.0265(12) 1.0000 Uiso D U . . . .
C4 C 0.9441(13) 0.2974(4) 0.3326(11) 0.0261(11) 1.0000 Uiso D U . . . .
C5 C 0.8034(13) 0.3400(4) 0.2968(11) 0.0244(11) 1.0000 Uiso D U . . . .
C7 C 0.6501(13) 0.3947(4) 0.5255(11) 0.0255(11) 1.0000 Uiso D U . . . .
C8 C 0.7902(14) 0.4342(4) 0.5922(11) 0.0286(12) 1.0000 Uiso D U . . . .
C9 C 0.7835(15) 0.4856(4) 0.7260(12) 0.0323(13) 1.0000 Uiso D U . . . .
C10 C 0.6347(14) 0.4978(5) 0.8030(12) 0.0319(13) 1.0000 Uiso D U . . . .
C11 C 0.4967(14) 0.4596(4) 0.7457(11) 0.0284(12) 1.0000 Uiso D U . . . .
C12 C 0.5026(13) 0.4077(4) 0.6104(11) 0.0282(11) 1.0000 Uiso D U . . . .
C16 C 0.9677(15) 0.2533(4) 0.4806(11) 0.0290(13) 1.0000 Uiso D U . . . .
C18 C 1.0892(16) 0.3647(4) -0.0724(12) 0.0272(14) 1.0000 Uiso D U . . . .
N6 N 0.6554(12) 0.3479(3) 0.3851(9) 0.0245(11) 1.0000 Uiso D U . . . .
N13 N 0.3465(12) 0.3736(4) 0.5496(10) 0.0325(11) 1.0000 Uiso D U . . . .
N17 N 0.9745(13) 0.2181(4) 0.6004(10) 0.0350(14) 1.0000 Uiso D U . . . .
O14 O 0.2189(11) 0.3976(3) 0.6164(9) 0.0400(12) 1.0000 Uiso D U . . . .
O15 O 0.3437(11) 0.3212(3) 0.4391(9) 0.0395(12) 1.0000 Uiso D U . . . .
H31 H 1.1662 0.2754 0.2152 0.0318 1.0000 Uiso R . . . . .
H61 H 0.5679 0.3232 0.3503 0.0301 1.0000 Uiso R . . . . .
H81 H 0.8910 0.4258 0.5439 0.0338 1.0000 Uiso R . . . . .
H91 H 0.8799 0.5121 0.7633 0.0392 1.0000 Uiso R . . . . .
H101 H 0.6286 0.5325 0.8950 0.0383 1.0000 Uiso R . . . . .
H111 H 0.3956 0.4670 0.7972 0.0342 1.0000 Uiso R . . . . .
H181 H 1.1995 0.3423 -0.0679 0.0410 1.0000 Uiso R . . . . .
H182 H 1.0915 0.4266 -0.0920 0.0409 1.0000 Uiso R . . . . .
H183 H 1.0292 0.3353 -0.1554 0.0408 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.038(2) 0.0291(9) 0.0245(17) 0.0038(9) 0.0089(18) 0.0045(10)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          2.15(5)
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 . C2 . 1.729(10) yes
S1 . C5 . 1.710(8) yes
C2 . C3 . 1.339(13) yes
C2 . C18 . 1.501(9) yes
C3 . C4 . 1.433(8) yes
C3 . H31 . 0.926 no
C4 . C5 . 1.344(13) yes
C4 . C16 . 1.431(12) yes
C5 . N6 . 1.425(9) yes
C7 . C8 . 1.400(14) yes
C7 . C12 . 1.414(10) yes
C7 . N6 . 1.385(10) yes
C8 . C9 . 1.375(11) yes
C8 . H81 . 0.926 no
C9 . C10 . 1.388(11) yes
C9 . H91 . 0.932 no
C10 . C11 . 1.348(15) yes
C10 . H101 . 0.941 no
C11 . C12 . 1.390(11) yes
C11 . H111 . 0.938 no
C12 . N13 . 1.459(13) yes
C16 . N17 . 1.147(11) yes
C18 . H181 . 0.958 no
C18 . H182 . 0.950 no
C18 . H183 . 0.961 no
N6 . H61 . 0.853 no
N13 . O14 . 1.238(8) yes
N13 . O15 . 1.226(9) yes
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
C2 . S1 . C5 . 91.7(5) yes
S1 . C2 . C3 . 111.4(5) yes
S1 . C2 . C18 . 118.4(8) yes
C3 . C2 . C18 . 130.2(9) yes
C2 . C3 . C4 . 112.4(9) yes
C2 . C3 . H31 . 124.1 no
C4 . C3 . H31 . 123.5 no
C3 . C4 . C5 . 113.0(8) yes
C3 . C4 . C16 . 125.0(9) yes
C5 . C4 . C16 . 122.0(7) yes
S1 . C5 . C4 . 111.5(5) yes
S1 . C5 . N6 . 118.6(8) yes
C4 . C5 . N6 . 129.7(8) yes
C8 . C7 . C12 . 115.0(8) yes
C8 . C7 . N6 . 122.4(7) yes
C12 . C7 . N6 . 122.6(9) yes
C7 . C8 . C9 . 122.5(8) yes
C7 . C8 . H81 . 118.7 no
C9 . C8 . H81 . 118.8 no
C8 . C9 . C10 . 120.1(11) yes
C8 . C9 . H91 . 118.9 no
C10 . C9 . H91 . 121.0 no
C9 . C10 . C11 . 119.8(9) yes
C9 . C10 . H101 . 120.9 no
C11 . C10 . H101 . 119.3 no
C10 . C11 . C12 . 120.3(8) yes
C10 . C11 . H111 . 120.5 no
C12 . C11 . H111 . 119.1 no
C7 . C12 . C11 . 122.1(10) yes
C7 . C12 . N13 . 120.5(8) yes
C11 . C12 . N13 . 117.1(7) yes
C4 . C16 . N17 . 175.1(11) yes
C2 . C18 . H181 . 108.4 no
C2 . C18 . H182 . 110.5 no
H181 . C18 . H182 . 109.6 no
C2 . C18 . H183 . 109.0 no
H181 . C18 . H183 . 109.6 no
H182 . C18 . H183 . 109.8 no
C5 . N6 . C7 . 121.6(9) yes
C5 . N6 . H61 . 119.0 no
C7 . N6 . H61 . 119.4 no
C12 . N13 . O14 . 117.5(7) yes
C12 . N13 . O15 . 120.6(7) yes
O14 . N13 . O15 . 121.8(10) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 16/12/14 at 13:39:50
#
#Refinement with riding constraints on H atoms
#LIST     12                                                                    
BLOCK SCALE X'S, 
CONT S(1,U'S) 
CONT C(2,U[ISO]) UNTIL O(15) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  18,X'S) H   ( 183,X'S) H   ( 182,X'S) H   ( 181,X'S) 
RIDE N   (   6,X'S) H   (  61,X'S) 
END    

#Refinement of hydrogen positions and U[iso] with restraints
#LIST 12
block
CONT H(   31 ,X,Y,Z,U[ISO])
CONT H(   81 ,X,Y,Z,U[ISO])
CONT H(   91 ,X,Y,Z,U[ISO])
CONT H(  101 ,X,Y,Z,U[ISO])
CONT H(  111 ,X,Y,Z,U[ISO])
CONT H(  183 ,X,Y,Z,U[ISO])
CONT H(  182 ,X,Y,Z,U[ISO])
CONT H(  181 ,X,Y,Z,U[ISO])
CONT H(   61 ,X,Y,Z,U[ISO])
END
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 16/12/14 at 13:39:50
#
#Non-H atom restraints
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
REM   DELU   START (DO NOT REMOVE THIS LINE) 
VIBR .0, 0.00200 = S(1) TO C(2) 
VIBR .0, 0.00200 = S(1) TO C(5) 
VIBR .0, 0.00500 = C(5) TO C(2) 
VIBR .0, 0.00200 = C(2) TO C(18) 
VIBR .0, 0.00200 = C(2) TO C(3) 
VIBR .0, 0.00500 = C(18) TO S(1) 
VIBR .0, 0.00500 = C(3) TO S(1) 
VIBR .0, 0.00500 = C(3) TO C(18) 
VIBR .0, 0.00200 = C(3) TO C(4) 
VIBR .0, 0.00500 = C(4) TO C(2) 
VIBR .0, 0.00200 = C(4) TO C(5) 
VIBR .0, 0.00200 = C(4) TO C(16) 
VIBR .0, 0.00500 = C(5) TO C(3) 
VIBR .0, 0.00500 = C(16) TO C(3) 
VIBR .0, 0.00500 = C(16) TO C(5) 
VIBR .0, 0.00200 = C(5) TO N(6) 
VIBR .0, 0.00500 = S(1) TO C(4) 
VIBR .0, 0.00500 = N(6) TO C(4) 
VIBR .0, 0.00500 = N(6) TO S(1) 
VIBR .0, 0.00200 = N(6) TO C(7) 
VIBR .0, 0.00500 = C(7) TO C(5) 
VIBR .0, 0.00200 = C(7) TO C(8) 
VIBR .0, 0.00200 = C(7) TO C(12) 
VIBR .0, 0.00500 = C(8) TO N(6) 
VIBR .0, 0.00500 = C(12) TO N(6) 
VIBR .0, 0.00500 = C(12) TO C(8) 
VIBR .0, 0.00200 = C(8) TO C(9) 
VIBR .0, 0.00500 = C(9) TO C(7) 
VIBR .0, 0.00200 = C(9) TO C(10) 
VIBR .0, 0.00500 = C(10) TO C(8) 
VIBR .0, 0.00200 = C(10) TO C(11) 
VIBR .0, 0.00500 = C(11) TO C(9) 
VIBR .0, 0.00200 = C(11) TO C(12) 
VIBR .0, 0.00500 = C(12) TO C(10) 
VIBR .0, 0.00200 = C(12) TO N(13) 
VIBR .0, 0.00500 = C(7) TO C(11) 
VIBR .0, 0.00500 = N(13) TO C(11) 
VIBR .0, 0.00500 = N(13) TO C(7) 
VIBR .0, 0.00200 = N(13) TO O(14) 
VIBR .0, 0.00200 = N(13) TO O(15) 
VIBR .0, 0.00500 = O(14) TO C(12) 
VIBR .0, 0.00500 = O(15) TO C(12) 
VIBR .0, 0.00500 = O(15) TO O(14) 
VIBR .0, 0.00200 = C(16) TO N(17) 
VIBR .0, 0.00500 = N(17) TO C(4) 
REM   DELU   END (DO NOT REMOVE THIS LINE) 
REM   THERMSIM   START (DO NOT REMOVE THIS LINE) 
U(IJ) .0, 0.04000 = S(1) TO C(2) 
U(IJ) .0, 0.04000 = S(1) TO C(5) 
U(IJ) .0, 0.08000 = C(2) TO C(18) 
U(IJ) .0, 0.04000 = C(2) TO C(3) 
U(IJ) .0, 0.04000 = C(3) TO C(4) 
U(IJ) .0, 0.04000 = C(4) TO C(5) 
U(IJ) .0, 0.04000 = C(4) TO C(16) 
U(IJ) .0, 0.04000 = C(5) TO N(6) 
U(IJ) .0, 0.04000 = N(6) TO C(7) 
U(IJ) .0, 0.04000 = C(7) TO C(8) 
U(IJ) .0, 0.04000 = C(7) TO C(12) 
U(IJ) .0, 0.04000 = C(8) TO C(9) 
U(IJ) .0, 0.04000 = C(9) TO C(10) 
U(IJ) .0, 0.04000 = C(10) TO C(11) 
U(IJ) .0, 0.04000 = C(11) TO C(12) 
U(IJ) .0, 0.04000 = C(12) TO N(13) 
U(IJ) .0, 0.08000 = N(13) TO O(14) 
U(IJ) .0, 0.08000 = N(13) TO O(15) 
U(IJ) .0, 0.08000 = C(16) TO N(17) 
REM   THERMSIM   END (DO NOT REMOVE THIS LINE) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
DISTANCE 1.220000 , 0.020000 = N(13) TO O(14) 
DISTANCE 1.220000 , 0.020000 = N(13) TO O(15) 
DISTANCE 1.450000 , 0.020000 = C(12) TO N(13) 
DISTANCE 1.390000 , 0.020000 = C(11) TO C(12) 
DISTANCE 1.360000 , 0.020000 = C(10) TO C(11) 
DISTANCE 1.390000 , 0.020000 = C(9) TO C(10) 
DISTANCE 1.370000 , 0.020000 = C(8) TO C(9) 
DISTANCE 1.400000 , 0.020000 = C(7) TO C(8) 
DISTANCE 1.410000 , 0.020000 = C(7) TO C(12) 
DISTANCE 1.370000 , 0.020000 = C(7) TO N(6) 
DISTANCE 1.400000 , 0.02000 = C(5) TO N(6) 
DISTANCE 1.720000 , 0.020000 = S(1) TO C(5) 
DISTANCE 1.720000 , 0.020000 = S(1) TO C(2) 
DISTANCE 1.350000 , 0.020000 = C(2) TO C(3) 
DISTANCE 1.430000 , 0.020000 = C(3) TO C(4) 
DISTANCE 1.360000 , 0.020000 = C(4) TO C(5) 
DISTANCE 1.430000 , 0.020000 = C(4) TO C(16) 
DISTANCE 1.140000 , 0.020000 = C(16) TO N(17) 
DISTANCE 1.500000 , 0.020000 = C(2) TO C(18) 
END            

#Restraints used for hydrogen refinement
#LIST 16
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 3) to H(31) 
REST 0.032, 0.002 = H(31,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(31) TO C ( 3) TO C(2) 
CONT H(31) TO C ( 3) TO C(4) 
PLANAR C ( 3) C(2) C(4) H(31) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 8) to H(81) 
REST 0.034, 0.002 = H(81,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(81) TO C ( 8) TO C(7) 
CONT H(81) TO C ( 8) TO C(9) 
PLANAR C ( 8) C(7) C(9) H(81) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 9) to H(91) 
REST 0.039, 0.002 = H(91,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(91) TO C ( 9) TO C(8) 
CONT H(91) TO C ( 9) TO C(10) 
PLANAR C ( 9) C(8) C(10) H(91) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 10) to H(101) 
REST 0.038, 0.002 = H(101,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(101) TO C ( 10) TO C(9) 
CONT H(101) TO C ( 10) TO C(11) 
PLANAR C ( 10) C(9) C(11) H(101) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 11) to H(111) 
REST 0.034, 0.002 = H(111,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(111) TO C ( 11) TO C(10) 
CONT H(111) TO C ( 11) TO C(12) 
PLANAR C ( 11) C(10) C(12) H(111) 
REM            3 H on sp 3
DIST 0.96, 0.02 = 
CONT C ( 18) to H(183) 
CONT C ( 18) to H(182) 
CONT C ( 18) to H(181) 
REST 0.041, 0.002 = H(183,U[ISO]) 
REST 0.041, 0.002 = H(182,U[ISO]) 
REST 0.041, 0.002 = H(181,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(2) to C ( 18) to H(183) 
CONT C(2) to C ( 18) to H(182) 
CONT C(2) to C ( 18) to H(181) 
ANGLE 0.0, 2.0 = mean H(183) to C ( 18) to H(182) 
CONT H(183) to C ( 18) to H(181) 
CONT H(182) to C ( 18) to H(181) 
REM            H1-N-R2
DIST 0.86, 0.02 = 
CONT N ( 6) to H(61) 
REST 0.030, 0.002 = H(61,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(61) TO N ( 6) TO C(5) 
CONT H(61) TO N ( 6) TO C(7) 
PLANAR 0.010000  C(5) C(7) N(6) H(61) 
END
;
_chemical_name_common            ROY
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_Y_1.89_GPa
_database_code_depnum_ccdc_archive 'CCDC 1058326'
_audit_update_record             
;
2015-04-07 deposited with the CCDC.
2015-05-20 downloaded from the CCDC.
;
_audit_creation_date             14-12-17
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'ROY_Y-form, 1.89 GPa'
_chemical_name_systematic        
5-methyl-2-((2-nitrophenyl)amino)-3-thiophenecarbonitrile


_exptl_special_details           
; 
The crystal was loaded in a Merrill-Bassett diamond anvil cell, using 4:1 
methanol:ethanol as a pressure-transmitting medium and ruby as a pressure 
marker. Pressure was measured before and after data collection and the average
of these - 1.89 GPa - was taken to be the experimental pressure.
;



_refine_special_details          
; 
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      18.56 Degree
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......      0.588 Note  
PLAT340_ALERT_3_B Low Bond Precision on  C-C Bonds ...............     0.0162 Ang.  
PLAT911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L=  0.589        698 Report
RINTA01_ALERT_3_C  The value of Rint is greater than 0.12   Rint given   0.136
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5889
PLAT020_ALERT_3_C The value of Rint is greater than 0.12 .........      0.136 Report
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large.      15.54 Why ? 
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          30 %     
PLAT910_ALERT_3_G Missing # of FCF Reflections Below Th(Min) .....          1 Report
PLAT960_ALERT_3_G Number of Intensities with I  <   - 2*sig(I) ...          5 Check  

Much of reciprocal space is unmeasurable, owing to the body of the diamond 
anvil cell, leading to missing reflections, low completeness and poor statistics.
Data are 54.7% complete to 0.85 Angstroms. Resolution and completeness 
statistics are given below.

#====================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#====================================================
Theta sin(th)/Lambda Complete  Expected Measured  Missing
#-------------------------------------------------------------------------------
 20.82     0.500     0.615         1060      652      408
 23.01     0.550     0.582         1400      815      585
 24.74     0.589     0.576         1650      951      699
------------------------------------------------------------ ACTA Min. Res. ---


PLAT921_ALERT_1_B R1  in the CIF and FCF Differ by ...............    -0.0149 Check 
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......     71.178 Check

Crystals labels omitted reflections with several different flags that describe 
the reason for their omission. PLATON does not recognise this format and 
these omitted reflections have been included in the calculation of R1 and K.


PLAT201_ALERT_2_A Isotropic non-H Atoms in Main Residue(s) .......         17 Report
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         18 Note  
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         18 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         64 Note  

Owing to poor data quality, only the relatively electron-rich sulfur atom could be 
refined anisotropically. Distance, vibration and thermal similarity restraints were 
necessary for a stable refinement. Previous variable-pressure experiments on 
organic materials have shown that pressure has little effect on covalent bond 
lengths and so the model has been restrained to the values observed at ambient 
pressure. The refinement procedure is discussed above and the restraints used 
are given at the end of this file.


PLAT157_ALERT_4_C Non-standard Monoclinic Beta Angle less 90 Deg        89.76 Degree
PLAT158_ALERT_4_G The Input Unitcell is NOT Standard/Reduced .....     Please Check 

The unit cell settings are intended to be consistent across the pressure series, over which
the beta angle decreases from >90 to <90 degrees.


PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do ! 

These are given further below.


PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check 
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check 

This is correct.


PLAT432_ALERT_2_G Short Inter X...Y Contact  O14    ..  C18     ..       2.88 Ang.  
PLAT432_ALERT_2_G Short Inter X...Y Contact  O14    ..  C8      ..       3.02 Ang.  

Short contacts are not unusual for high-pressure structures.
;


_cell_length_a                   8.0755(16)
_cell_length_b                   14.874(3)
_cell_length_c                   8.4734(17)
_cell_angle_alpha                90
_cell_angle_beta                 89.76(3)
_cell_angle_gamma                90
_cell_volume                     1017.7(4)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-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 =      1.69 Fooo =    536.00 Mu =      3.14 M =    259.29
# Found Formula = C12 H9 N3 O2 S1 
# Dc =      1.69 FOOO =    536.00 Mu =      3.14 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    855
_cell_measurement_theta_min      3
_cell_measurement_theta_max      23
_cell_measurement_temperature    293

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_max          0.153

_exptl_crystal_density_diffrn    1.692
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.314

# Sheldrick geometric approximatio 0.97 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ


_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'User-defined model'
_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         1.89 #GPa
_diffrn_reflns_number            5263
_reflns_number_total             951
_diffrn_reflns_av_R_equivalents  0.136
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 951 
# Theoretical number of reflections is about 3483 


_diffrn_reflns_theta_min         2.767
_diffrn_reflns_theta_max         24.745
_diffrn_measured_fraction_theta_max 0.547

_diffrn_reflns_theta_full        18.559
_diffrn_measured_fraction_theta_full 0.588


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_reflns_limit_h_min              -8
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              8

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.99
_refine_diff_density_max         1.18


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         943
_refine_ls_number_restraints     64
_refine_ls_number_parameters     78
_oxford_refine_ls_R_factor_ref   0.1545
_refine_ls_wR_factor_ref         0.2159
_refine_ls_goodness_of_fit_ref   0.9791
_refine_ls_shift/su_max          0.0000573
_refine_ls_shift/su_mean         0.0000100


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        945
_refine_ls_R_factor_all          0.1551
_refine_ls_wR_factor_all         0.2193

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                563
_refine_ls_R_factor_gt           0.0950
_refine_ls_wR_factor_gt          0.1810

_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.01P)² +15.54P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;


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 0.8141(4) 0.38368(19) 0.1110(4) 0.0226 1.0000 Uani D U . . . .
C2 C 1.0128(13) 0.3449(7) 0.0808(13) 0.0207(13) 1.0000 Uiso D U . . . .
C3 C 1.0684(14) 0.2992(7) 0.2059(13) 0.0209(14) 1.0000 Uiso D U . . . .
C4 C 0.9502(13) 0.2967(7) 0.3322(13) 0.0210(13) 1.0000 Uiso D U . . . .
C5 C 0.8088(12) 0.3406(7) 0.2972(13) 0.0207(13) 1.0000 Uiso D U . . . .
C7 C 0.6549(14) 0.3954(7) 0.5292(14) 0.0255(13) 1.0000 Uiso D U . . . .
C8 C 0.7953(15) 0.4349(7) 0.5958(15) 0.0274(15) 1.0000 Uiso D U . . . .
C9 C 0.7877(16) 0.4837(7) 0.7306(15) 0.0301(16) 1.0000 Uiso D U . . . .
C10 C 0.6382(14) 0.4981(8) 0.8077(16) 0.0308(16) 1.0000 Uiso D U . . . .
C11 C 0.4992(15) 0.4602(7) 0.7489(15) 0.0292(15) 1.0000 Uiso D U . . . .
C12 C 0.5064(13) 0.4095(7) 0.6139(14) 0.0276(13) 1.0000 Uiso D U . . . .
C16 C 0.9726(15) 0.2536(7) 0.4807(14) 0.0234(16) 1.0000 Uiso D U . . . .
C18 C 1.0951(15) 0.3631(7) -0.0725(15) 0.0224(17) 1.0000 Uiso D U . . . .
N6 N 0.6620(12) 0.3501(5) 0.3883(12) 0.0232(13) 1.0000 Uiso D U . . . .
N13 N 0.3496(12) 0.3763(6) 0.5506(13) 0.0294(14) 1.0000 Uiso D U . . . .
N17 N 0.9813(12) 0.2184(6) 0.6015(13) 0.0265(18) 1.0000 Uiso D U . . . .
O14 O 0.2206(11) 0.4021(5) 0.6158(11) 0.0324(16) 1.0000 Uiso D U . . . .
O15 O 0.3473(11) 0.3230(5) 0.4406(11) 0.0313(16) 1.0000 Uiso D U . . . .
H31 H 1.1716 0.2717 0.2104 0.0261 1.0000 Uiso R . . . . .
H81 H 0.8966 0.4270 0.5465 0.0330 1.0000 Uiso R . . . . .
H91 H 0.8848 0.5083 0.7710 0.0341 1.0000 Uiso R . . . . .
H101 H 0.6335 0.5334 0.8982 0.0351 1.0000 Uiso R . . . . .
H111 H 0.3975 0.4682 0.8003 0.0342 1.0000 Uiso R . . . . .
H182 H 1.2054 0.3383 -0.0708 0.0320 1.0000 Uiso R . . . . .
H181 H 1.1007 0.4273 -0.0913 0.0319 1.0000 Uiso R . . . . .
H183 H 1.0319 0.3344 -0.1548 0.0320 1.0000 Uiso R . . . . .
H61 H 0.5728 0.3259 0.3533 0.0282 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0184(19) 0.0322(18) 0.017(2) 0.0021(13) -0.0033(18) 0.0012(12)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.2484(7)
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 . C2 . 1.723(9) yes
S1 . C5 . 1.703(10) yes
C2 . C3 . 1.339(14) yes
C2 . C18 . 1.482(11) yes
C3 . C4 . 1.432(11) yes
C3 . H31 . 0.929 no
C4 . C5 . 1.349(12) yes
C4 . C16 . 1.425(13) yes
C5 . N6 . 1.420(10) yes
C7 . C8 . 1.398(13) yes
C7 . C12 . 1.411(11) yes
C7 . N6 . 1.372(12) yes
C8 . C9 . 1.355(13) yes
C8 . H81 . 0.925 no
C9 . C10 . 1.387(11) yes
C9 . H91 . 0.932 no
C10 . C11 . 1.353(14) yes
C10 . H101 . 0.930 no
C11 . C12 . 1.371(13) yes
C11 . H111 . 0.936 no
C12 . N13 . 1.464(13) yes
C16 . N17 . 1.152(12) yes
C18 . H182 . 0.964 no
C18 . H181 . 0.968 no
C18 . H183 . 0.965 no
N6 . H61 . 0.859 no
N13 . O14 . 1.238(9) yes
N13 . O15 . 1.224(11) yes
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
C2 . S1 . C5 . 91.8(5) yes
S1 . C2 . C3 . 111.6(7) yes
S1 . C2 . C18 . 118.9(8) yes
C3 . C2 . C18 . 129.5(9) yes
C2 . C3 . C4 . 112.3(10) yes
C2 . C3 . H31 . 124.1 no
C4 . C3 . H31 . 123.6 no
C3 . C4 . C5 . 112.7(10) yes
C3 . C4 . C16 . 125.8(10) yes
C5 . C4 . C16 . 121.5(8) yes
S1 . C5 . C4 . 111.6(7) yes
S1 . C5 . N6 . 118.9(8) yes
C4 . C5 . N6 . 129.4(10) yes
C8 . C7 . C12 . 114.9(10) yes
C8 . C7 . N6 . 121.8(9) yes
C12 . C7 . N6 . 123.2(10) yes
C7 . C8 . C9 . 122.1(10) yes
C7 . C8 . H81 . 118.9 no
C9 . C8 . H81 . 119.0 no
C8 . C9 . C10 . 121.1(13) yes
C8 . C9 . H91 . 119.0 no
C10 . C9 . H91 . 119.9 no
C9 . C10 . C11 . 118.9(12) yes
C9 . C10 . H101 . 120.6 no
C11 . C10 . H101 . 120.5 no
C10 . C11 . C12 . 120.3(10) yes
C10 . C11 . H111 . 120.2 no
C12 . C11 . H111 . 119.5 no
C7 . C12 . C11 . 122.6(11) yes
C7 . C12 . N13 . 119.9(10) yes
C11 . C12 . N13 . 117.3(9) yes
C4 . C16 . N17 . 176.2(13) yes
C2 . C18 . H182 . 109.1 no
C2 . C18 . H181 . 110.2 no
H182 . C18 . H181 . 109.8 no
C2 . C18 . H183 . 108.3 no
H182 . C18 . H183 . 109.4 no
H181 . C18 . H183 . 109.9 no
C5 . N6 . C7 . 123.6(10) yes
C5 . N6 . H61 . 118.1 no
C7 . N6 . H61 . 118.3 no
C12 . N13 . O14 . 117.3(9) yes
C12 . N13 . O15 . 120.9(8) yes
O14 . N13 . O15 . 121.7(10) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 17/12/14 at 12:31:10
#
#Refinement with riding constraints on H atoms
#LIST     12                                                                    
BLOCK SCALE X'S, 
CONT S(1,U'S) 
CONT C(2,U[ISO]) UNTIL O(15) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  18,X'S) H   ( 183,X'S) H   ( 182,X'S) H   ( 181,X'S) 
RIDE N   (   6,X'S) H   (  61,X'S) 
END        

#Refinement of hydrogen positions and U[iso] with restraints
#LIST 12
block
CONT H(   31 ,X,Y,Z,U[ISO])
CONT H(   81 ,X,Y,Z,U[ISO])
CONT H(   91 ,X,Y,Z,U[ISO])
CONT H(  101 ,X,Y,Z,U[ISO])
CONT H(  111 ,X,Y,Z,U[ISO])
CONT H(  183 ,X,Y,Z,U[ISO])
CONT H(  182 ,X,Y,Z,U[ISO])
CONT H(  181 ,X,Y,Z,U[ISO])
CONT H(   61 ,X,Y,Z,U[ISO])
END
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 17/12/14 at 12:31:10
#
#Non-H atom restraints
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
REM   DELU   START (DO NOT REMOVE THIS LINE) 
VIBR .0, 0.00200 = S(1) TO C(2) 
VIBR .0, 0.00200 = S(1) TO C(5) 
VIBR .0, 0.00500 = C(5) TO C(2) 
VIBR .0, 0.00200 = C(2) TO C(18) 
VIBR .0, 0.00200 = C(2) TO C(3) 
VIBR .0, 0.00500 = C(18) TO S(1) 
VIBR .0, 0.00500 = C(3) TO S(1) 
VIBR .0, 0.00500 = C(3) TO C(18) 
VIBR .0, 0.00200 = C(3) TO C(4) 
VIBR .0, 0.00500 = C(4) TO C(2) 
VIBR .0, 0.00200 = C(4) TO C(5) 
VIBR .0, 0.00200 = C(4) TO C(16) 
VIBR .0, 0.00500 = C(5) TO C(3) 
VIBR .0, 0.00500 = C(16) TO C(3) 
VIBR .0, 0.00500 = C(16) TO C(5) 
VIBR .0, 0.00200 = C(5) TO N(6) 
VIBR .0, 0.00500 = S(1) TO C(4) 
VIBR .0, 0.00500 = N(6) TO C(4) 
VIBR .0, 0.00500 = N(6) TO S(1) 
VIBR .0, 0.00200 = N(6) TO C(7) 
VIBR .0, 0.00500 = C(7) TO C(5) 
VIBR .0, 0.00200 = C(7) TO C(8) 
VIBR .0, 0.00200 = C(7) TO C(12) 
VIBR .0, 0.00500 = C(8) TO N(6) 
VIBR .0, 0.00500 = C(12) TO N(6) 
VIBR .0, 0.00500 = C(12) TO C(8) 
VIBR .0, 0.00200 = C(8) TO C(9) 
VIBR .0, 0.00500 = C(9) TO C(7) 
VIBR .0, 0.00200 = C(9) TO C(10) 
VIBR .0, 0.00500 = C(10) TO C(8) 
VIBR .0, 0.00200 = C(10) TO C(11) 
VIBR .0, 0.00500 = C(11) TO C(9) 
VIBR .0, 0.00200 = C(11) TO C(12) 
VIBR .0, 0.00500 = C(12) TO C(10) 
VIBR .0, 0.00200 = C(12) TO N(13) 
VIBR .0, 0.00500 = C(7) TO C(11) 
VIBR .0, 0.00500 = N(13) TO C(11) 
VIBR .0, 0.00500 = N(13) TO C(7) 
VIBR .0, 0.00200 = N(13) TO O(14) 
VIBR .0, 0.00200 = N(13) TO O(15) 
VIBR .0, 0.00500 = O(14) TO C(12) 
VIBR .0, 0.00500 = O(15) TO C(12) 
VIBR .0, 0.00500 = O(15) TO O(14) 
VIBR .0, 0.00200 = C(16) TO N(17) 
VIBR .0, 0.00500 = N(17) TO C(4) 
REM   DELU   END (DO NOT REMOVE THIS LINE) 
REM   THERMSIM   START (DO NOT REMOVE THIS LINE) 
U(IJ) .0, 0.04000 = S(1) TO C(2) 
U(IJ) .0, 0.04000 = S(1) TO C(5) 
U(IJ) .0, 0.08000 = C(2) TO C(18) 
U(IJ) .0, 0.04000 = C(2) TO C(3) 
U(IJ) .0, 0.04000 = C(3) TO C(4) 
U(IJ) .0, 0.04000 = C(4) TO C(5) 
U(IJ) .0, 0.04000 = C(4) TO C(16) 
U(IJ) .0, 0.04000 = C(5) TO N(6) 
U(IJ) .0, 0.04000 = N(6) TO C(7) 
U(IJ) .0, 0.04000 = C(7) TO C(8) 
U(IJ) .0, 0.04000 = C(7) TO C(12) 
U(IJ) .0, 0.04000 = C(8) TO C(9) 
U(IJ) .0, 0.04000 = C(9) TO C(10) 
U(IJ) .0, 0.04000 = C(10) TO C(11) 
U(IJ) .0, 0.04000 = C(11) TO C(12) 
U(IJ) .0, 0.04000 = C(12) TO N(13) 
U(IJ) .0, 0.08000 = N(13) TO O(14) 
U(IJ) .0, 0.08000 = N(13) TO O(15) 
U(IJ) .0, 0.08000 = C(16) TO N(17) 
REM   THERMSIM   END (DO NOT REMOVE THIS LINE) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
DISTANCE 1.220000 , 0.020000 = N(13) TO O(14) 
DISTANCE 1.220000 , 0.020000 = N(13) TO O(15) 
DISTANCE 1.450000 , 0.020000 = C(12) TO N(13) 
DISTANCE 1.390000 , 0.020000 = C(11) TO C(12) 
DISTANCE 1.360000 , 0.020000 = C(10) TO C(11) 
DISTANCE 1.390000 , 0.020000 = C(9) TO C(10) 
DISTANCE 1.370000 , 0.020000 = C(8) TO C(9) 
DISTANCE 1.400000 , 0.020000 = C(7) TO C(8) 
DISTANCE 1.410000 , 0.020000 = C(7) TO C(12) 
DISTANCE 1.370000 , 0.020000 = C(7) TO N(6) 
DISTANCE 1.400000 , 0.02000 = C(5) TO N(6) 
DISTANCE 1.720000 , 0.020000 = S(1) TO C(5) 
DISTANCE 1.720000 , 0.020000 = S(1) TO C(2) 
DISTANCE 1.350000 , 0.020000 = C(2) TO C(3) 
DISTANCE 1.430000 , 0.020000 = C(3) TO C(4) 
DISTANCE 1.360000 , 0.020000 = C(4) TO C(5) 
DISTANCE 1.430000 , 0.020000 = C(4) TO C(16) 
DISTANCE 1.140000 , 0.020000 = C(16) TO N(17) 
DISTANCE 1.500000 , 0.020000 = C(2) TO C(18) 
END             

#Restraints used for hydrogen refinement
#LIST 16
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 3) to H(31) 
REST 0.026, 0.002 = H(31,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(31) TO C ( 3) TO C(2) 
CONT H(31) TO C ( 3) TO C(4) 
PLANAR C ( 3) C(2) C(4) H(31) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 8) to H(81) 
REST 0.033, 0.002 = H(81,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(81) TO C ( 8) TO C(7) 
CONT H(81) TO C ( 8) TO C(9) 
PLANAR C ( 8) C(7) C(9) H(81) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 9) to H(91) 
REST 0.034, 0.002 = H(91,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(91) TO C ( 9) TO C(8) 
CONT H(91) TO C ( 9) TO C(10) 
PLANAR C ( 9) C(8) C(10) H(91) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 10) to H(101) 
REST 0.035, 0.002 = H(101,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(101) TO C ( 10) TO C(9) 
CONT H(101) TO C ( 10) TO C(11) 
PLANAR C ( 10) C(9) C(11) H(101) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 11) to H(111) 
REST 0.034, 0.002 = H(111,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(111) TO C ( 11) TO C(10) 
CONT H(111) TO C ( 11) TO C(12) 
PLANAR C ( 11) C(10) C(12) H(111) 
REM            3 H on sp 3
DIST 0.96, 0.02 = 
CONT C ( 18) to H(183) 
CONT C ( 18) to H(182) 
CONT C ( 18) to H(181) 
REST 0.032, 0.002 = H(183,U[ISO]) 
REST 0.032, 0.002 = H(182,U[ISO]) 
REST 0.032, 0.002 = H(181,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(2) to C ( 18) to H(183) 
CONT C(2) to C ( 18) to H(182) 
CONT C(2) to C ( 18) to H(181) 
ANGLE 0.0, 2.0 = mean H(183) to C ( 18) to H(182) 
CONT H(183) to C ( 18) to H(181) 
CONT H(182) to C ( 18) to H(181) 
REM            H1-N-R2
DIST 0.86, 0.02 = 
CONT N ( 6) to H(61) 
REST 0.028, 0.002 = H(61,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(61) TO N ( 6) TO C(5) 
CONT H(61) TO N ( 6) TO C(7) 
PLANAR 0.010000  C(5) C(7) N(6) H(61) 
END
;
_chemical_name_common            ROY
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_Y_2.84_GPa
_database_code_depnum_ccdc_archive 'CCDC 1058327'
_audit_update_record             
;
2015-04-07 deposited with the CCDC.
2015-05-20 downloaded from the CCDC.
;
_audit_creation_date             14-12-16
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'ROY_Y-form, 2.84 GPa'
_chemical_name_systematic        
5-methyl-2-((2-nitrophenyl)amino)-3-thiophenecarbonitrile


_exptl_special_details           
; 
The crystal was loaded in a Merrill-Bassett diamond anvil cell, using 4:1 
methanol:ethanol as a pressure-transmitting medium and ruby as a pressure 
marker. Pressure was measured before and after data collection and the average
of these - 2.84 GPa - was taken to be the experimental pressure.
;


_refine_special_details          
; 
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      18.53 Degree
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......      0.658 Note  
PLAT911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L=  0.588        577 Report
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5882
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0092 Ang.  
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large.       6.77 Why ? 
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          65 %     
PLAT960_ALERT_3_G Number of Intensities with I  <   - 2*sig(I) ...          3 Check 

Much of reciprocal space is unmeasurable, owing to the body of the diamond 
anvil cell, leading to missing reflections, low completeness and poor statistics.
Data are 62.6 complete to 0.85 Angstroms. Resolution and completeness 
statistics are given below.

#====================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#====================================================
Theta sin(th)/Lambda Complete  Expected Measured  Missing
#-------------------------------------------------------------------------------
 20.82     0.500     0.689         1029      709      320
 23.01     0.550     0.659         1355      893      462
 24.71     0.588     0.645         1625     1048      577
------------------------------------------------------------ ACTA Min. Res. ---


PLAT921_ALERT_1_B R1  in the CIF and FCF Differ by ...............    -0.0139 Check 
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......     54.976 Check 

Crystals labels omitted reflections with several different flags that describe 
the reason for their omission. PLATON does not recognise this format and 
these omitted reflections have been included in the calculation of R1 and K.


PLAT201_ALERT_2_A Isotropic non-H Atoms in Main Residue(s) .......         17 Report
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         18 Note  
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         18 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         64 Note  

Owing to poor data quality, only the relatively electron-rich sulfur atom could be 
refined anisotropically. Distance, vibration and thermal similarity restraints were 
necessary for a stable refinement. Previous variable-pressure experiments on 
organic materials have shown that pressure has little effect on covalent bond 
lengths and so the model has been restrained to the values observed at ambient 
pressure. The refinement procedure is discussed above and the restraints used 
are given at the end of this file.


PLAT157_ALERT_4_C Non-standard Monoclinic Beta Angle less 90 Deg        89.15 Degree
PLAT158_ALERT_4_G The Input Unitcell is NOT Standard/Reduced .....     Please Check

The unit cell settings are intended to be consistent across the pressure series, over which
the beta angle decreases from >90 to <90 degrees.


PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !

These are given further below.


PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check 
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check 

This is correct.


PLAT432_ALERT_2_G Short Inter X...Y Contact  O14    ..  C18     ..       2.84 Ang.  
And 4 similar alerts

Short contacts are not unusual for high-pressure structures.
;

_cell_length_a                   8.0025(16)
_cell_length_b                   14.448(3)
_cell_length_c                   8.4923(17)
_cell_angle_alpha                90
_cell_angle_beta                 89.15(3)
_cell_angle_gamma                90
_cell_volume                     981.8(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-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 =      1.75 Fooo =    536.00 Mu =      3.26 M =    259.29
# Found Formula = C12 H9 N3 O2 S1 
# Dc =      1.75 FOOO =    536.00 Mu =      3.26 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    1896
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25
_cell_measurement_temperature    293

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_max          0.153

_exptl_crystal_density_diffrn    1.754
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.326

# Sheldrick geometric approximatio 0.97 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.51
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ


_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'User-defined model'
_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         2.84 #GPa
_diffrn_reflns_number            5974
_reflns_number_total             1048
_diffrn_reflns_av_R_equivalents  0.051
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1048 
# Theoretical number of reflections is about 3347 


_diffrn_reflns_theta_min         2.782
_diffrn_reflns_theta_max         24.711
_diffrn_measured_fraction_theta_max 0.626

_diffrn_reflns_theta_full        18.533
_diffrn_measured_fraction_theta_full 0.658


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              8

_oxford_diffrn_Wilson_B_factor   1.48
_oxford_diffrn_Wilson_scale      29.68

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

_refine_diff_density_min         -0.70
_refine_diff_density_max         0.67


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>0.0\s(I)
_refine_ls_number_reflns         1041
_refine_ls_number_restraints     64
_refine_ls_number_parameters     78
_oxford_refine_ls_R_factor_ref   0.0882
_refine_ls_wR_factor_ref         0.1844
_refine_ls_goodness_of_fit_ref   0.9946
_refine_ls_shift/su_max          0.0001365
_refine_ls_shift/su_mean         0.0000134


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1041
_refine_ls_R_factor_all          0.0882
_refine_ls_wR_factor_all         0.1844

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                803
_refine_ls_R_factor_gt           0.0664
_refine_ls_wR_factor_gt          0.1657

_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.07P)² + 6.77P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

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


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 0.8217(2) 0.38244(11) 0.1096(2) 0.0206 1.0000 Uani D U . . . .
C2 C 1.0223(7) 0.3410(4) 0.0792(8) 0.0188(10) 1.0000 Uiso D U . . . .
C3 C 1.0795(8) 0.2979(4) 0.2081(8) 0.0177(10) 1.0000 Uiso D U . . . .
C4 C 0.9598(7) 0.2977(4) 0.3351(8) 0.0185(10) 1.0000 Uiso D U . . . .
C5 C 0.8134(7) 0.3417(4) 0.2979(8) 0.0176(10) 1.0000 Uiso D U . . . .
C7 C 0.6603(7) 0.3970(4) 0.5321(8) 0.0188(10) 1.0000 Uiso D U . . . .
C8 C 0.8029(8) 0.4335(4) 0.6018(8) 0.0220(11) 1.0000 Uiso D U . . . .
C9 C 0.7945(9) 0.4821(4) 0.7388(9) 0.0258(11) 1.0000 Uiso D U . . . .
C10 C 0.6427(8) 0.4968(4) 0.8173(9) 0.0266(11) 1.0000 Uiso D U . . . .
C11 C 0.5028(8) 0.4609(4) 0.7553(9) 0.0239(11) 1.0000 Uiso D U . . . .
C12 C 0.5079(8) 0.4124(4) 0.6137(8) 0.0213(10) 1.0000 Uiso D U . . . .
C16 C 0.9801(8) 0.2535(4) 0.4832(8) 0.0211(11) 1.0000 Uiso D U . . . .
C18 C 1.1046(8) 0.3602(4) -0.0755(8) 0.0214(12) 1.0000 Uiso D U . . . .
N6 N 0.6686(6) 0.3535(3) 0.3892(7) 0.0188(10) 1.0000 Uiso D U . . . .
N13 N 0.3510(7) 0.3807(3) 0.5532(7) 0.0239(10) 1.0000 Uiso D U . . . .
N17 N 0.9878(7) 0.2179(4) 0.6037(7) 0.0268(12) 1.0000 Uiso D U . . . .
O14 O 0.2215(6) 0.4075(3) 0.6177(6) 0.0293(10) 1.0000 Uiso D U . . . .
O15 O 0.3498(6) 0.3283(3) 0.4394(6) 0.0290(10) 1.0000 Uiso D U . . . .
H31 H 1.1853 0.2716 0.2149 0.0214 1.0000 Uiso R . . . . .
H81 H 0.9069 0.4241 0.5530 0.0259 1.0000 Uiso R . . . . .
H91 H 0.8933 0.5070 0.7795 0.0310 1.0000 Uiso R . . . . .
H101 H 0.6374 0.5320 0.9095 0.0319 1.0000 Uiso R . . . . .
H111 H 0.4009 0.4691 0.8075 0.0292 1.0000 Uiso R . . . . .
H182 H 1.2182 0.3385 -0.0743 0.0320 1.0000 Uiso R . . . . .
H181 H 1.1047 0.4254 -0.0968 0.0321 1.0000 Uiso R . . . . .
H183 H 1.0458 0.3285 -0.1571 0.0322 1.0000 Uiso R . . . . .
H61 H 0.5778 0.3323 0.3526 0.0228 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0203(10) 0.0247(10) 0.0167(13) 0.0023(6) -0.0021(9) 0.0021(6)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.1913(4)
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 . C2 . 1.729(6) yes
S1 . C5 . 1.704(6) yes
C2 . C3 . 1.345(9) yes
C2 . C18 . 1.487(8) yes
C3 . C4 . 1.432(7) yes
C3 . H31 . 0.931 no
C4 . C5 . 1.373(8) yes
C4 . C16 . 1.422(9) yes
C5 . N6 . 1.395(6) yes
C7 . C8 . 1.397(9) yes
C7 . C12 . 1.412(7) yes
C7 . N6 . 1.367(8) yes
C8 . C9 . 1.360(9) yes
C8 . H81 . 0.934 no
C9 . C10 . 1.393(8) yes
C9 . H91 . 0.939 no
C10 . C11 . 1.348(9) yes
C10 . H101 . 0.934 no
C11 . C12 . 1.391(9) yes
C11 . H111 . 0.930 no
C12 . N13 . 1.438(8) yes
C16 . N17 . 1.148(8) yes
C18 . H182 . 0.962 no
C18 . H181 . 0.959 no
C18 . H183 . 0.959 no
N6 . H61 . 0.852 no
N13 . O14 . 1.228(6) yes
N13 . O15 . 1.228(7) yes
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
C2 . S1 . C5 . 92.5(3) yes
S1 . C2 . C3 . 111.4(4) yes
S1 . C2 . C18 . 117.7(5) yes
C3 . C2 . C18 . 130.8(6) yes
C2 . C3 . C4 . 112.4(6) yes
C2 . C3 . H31 . 124.1 no
C4 . C3 . H31 . 123.5 no
C3 . C4 . C5 . 112.9(6) yes
C3 . C4 . C16 . 125.7(6) yes
C5 . C4 . C16 . 121.4(5) yes
C4 . C5 . S1 . 110.7(4) yes
C4 . C5 . N6 . 129.3(6) yes
S1 . C5 . N6 . 120.0(5) yes
C8 . C7 . C12 . 115.9(6) yes
C8 . C7 . N6 . 121.4(5) yes
C12 . C7 . N6 . 122.6(6) yes
C7 . C8 . C9 . 121.9(6) yes
C7 . C8 . H81 . 119.0 no
C9 . C8 . H81 . 119.1 no
C8 . C9 . C10 . 121.3(7) yes
C8 . C9 . H91 . 118.8 no
C10 . C9 . H91 . 120.0 no
C9 . C10 . C11 . 118.5(7) yes
C9 . C10 . H101 . 120.8 no
C11 . C10 . H101 . 120.6 no
C10 . C11 . C12 . 121.2(6) yes
C10 . C11 . H111 . 119.4 no
C12 . C11 . H111 . 119.4 no
C7 . C12 . C11 . 121.2(6) yes
C7 . C12 . N13 . 121.8(6) yes
C11 . C12 . N13 . 117.0(5) yes
C4 . C16 . N17 . 176.5(7) yes
C2 . C18 . H182 . 109.6 no
C2 . C18 . H181 . 110.4 no
H182 . C18 . H181 . 108.8 no
C2 . C18 . H183 . 109.5 no
H182 . C18 . H183 . 109.1 no
H181 . C18 . H183 . 109.3 no
C5 . N6 . C7 . 125.4(6) yes
C5 . N6 . H61 . 117.3 no
C7 . N6 . H61 . 117.3 no
C12 . N13 . O14 . 118.4(5) yes
C12 . N13 . O15 . 119.7(5) yes
O14 . N13 . O15 . 122.0(6) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 16/12/14 at 16:41:31
#
#Refinement with riding constraints on H atoms
#LIST     12                                                                    
BLOCK SCALE X'S, 
CONT S(1,U'S) 
CONT C(2,U[ISO]) UNTIL O(15) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  18,X'S) H   ( 183,X'S) H   ( 182,X'S) H   ( 181,X'S) 
RIDE N   (   6,X'S) H   (  61,X'S) 
END                         

#Refinement of hydrogen positions and U[iso] with restraints
#LIST 12
block
CONT H(   31 ,X,Y,Z,U[ISO])
CONT H(   81 ,X,Y,Z,U[ISO])
CONT H(   91 ,X,Y,Z,U[ISO])
CONT H(  101 ,X,Y,Z,U[ISO])
CONT H(  111 ,X,Y,Z,U[ISO])
CONT H(  183 ,X,Y,Z,U[ISO])
CONT H(  182 ,X,Y,Z,U[ISO])
CONT H(  181 ,X,Y,Z,U[ISO])
CONT H(   61 ,X,Y,Z,U[ISO])
END
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 16/12/14 at 16:41:31
#
#Non-H atom restraints
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
REM   DELU   START (DO NOT REMOVE THIS LINE) 
VIBR .0, 0.00200 = S(1) TO C(2) 
VIBR .0, 0.00200 = S(1) TO C(5) 
VIBR .0, 0.00500 = C(5) TO C(2) 
VIBR .0, 0.00200 = C(2) TO C(18) 
VIBR .0, 0.00200 = C(2) TO C(3) 
VIBR .0, 0.00500 = C(18) TO S(1) 
VIBR .0, 0.00500 = C(3) TO S(1) 
VIBR .0, 0.00500 = C(3) TO C(18) 
VIBR .0, 0.00200 = C(3) TO C(4) 
VIBR .0, 0.00500 = C(4) TO C(2) 
VIBR .0, 0.00200 = C(4) TO C(5) 
VIBR .0, 0.00200 = C(4) TO C(16) 
VIBR .0, 0.00500 = C(5) TO C(3) 
VIBR .0, 0.00500 = C(16) TO C(3) 
VIBR .0, 0.00500 = C(16) TO C(5) 
VIBR .0, 0.00200 = C(5) TO N(6) 
VIBR .0, 0.00500 = S(1) TO C(4) 
VIBR .0, 0.00500 = N(6) TO C(4) 
VIBR .0, 0.00500 = N(6) TO S(1) 
VIBR .0, 0.00200 = N(6) TO C(7) 
VIBR .0, 0.00500 = C(7) TO C(5) 
VIBR .0, 0.00200 = C(7) TO C(8) 
VIBR .0, 0.00200 = C(7) TO C(12) 
VIBR .0, 0.00500 = C(8) TO N(6) 
VIBR .0, 0.00500 = C(12) TO N(6) 
VIBR .0, 0.00500 = C(12) TO C(8) 
VIBR .0, 0.00200 = C(8) TO C(9) 
VIBR .0, 0.00500 = C(9) TO C(7) 
VIBR .0, 0.00200 = C(9) TO C(10) 
VIBR .0, 0.00500 = C(10) TO C(8) 
VIBR .0, 0.00200 = C(10) TO C(11) 
VIBR .0, 0.00500 = C(11) TO C(9) 
VIBR .0, 0.00200 = C(11) TO C(12) 
VIBR .0, 0.00500 = C(12) TO C(10) 
VIBR .0, 0.00200 = C(12) TO N(13) 
VIBR .0, 0.00500 = C(7) TO C(11) 
VIBR .0, 0.00500 = N(13) TO C(11) 
VIBR .0, 0.00500 = N(13) TO C(7) 
VIBR .0, 0.00200 = N(13) TO O(14) 
VIBR .0, 0.00200 = N(13) TO O(15) 
VIBR .0, 0.00500 = O(14) TO C(12) 
VIBR .0, 0.00500 = O(15) TO C(12) 
VIBR .0, 0.00500 = O(15) TO O(14) 
VIBR .0, 0.00200 = C(16) TO N(17) 
VIBR .0, 0.00500 = N(17) TO C(4) 
REM   DELU   END (DO NOT REMOVE THIS LINE) 
REM   THERMSIM   START (DO NOT REMOVE THIS LINE) 
U(IJ) .0, 0.04000 = S(1) TO C(2) 
U(IJ) .0, 0.04000 = S(1) TO C(5) 
U(IJ) .0, 0.08000 = C(2) TO C(18) 
U(IJ) .0, 0.04000 = C(2) TO C(3) 
U(IJ) .0, 0.04000 = C(3) TO C(4) 
U(IJ) .0, 0.04000 = C(4) TO C(5) 
U(IJ) .0, 0.04000 = C(4) TO C(16) 
U(IJ) .0, 0.04000 = C(5) TO N(6) 
U(IJ) .0, 0.04000 = N(6) TO C(7) 
U(IJ) .0, 0.04000 = C(7) TO C(8) 
U(IJ) .0, 0.04000 = C(7) TO C(12) 
U(IJ) .0, 0.04000 = C(8) TO C(9) 
U(IJ) .0, 0.04000 = C(9) TO C(10) 
U(IJ) .0, 0.04000 = C(10) TO C(11) 
U(IJ) .0, 0.04000 = C(11) TO C(12) 
U(IJ) .0, 0.04000 = C(12) TO N(13) 
U(IJ) .0, 0.08000 = N(13) TO O(14) 
U(IJ) .0, 0.08000 = N(13) TO O(15) 
U(IJ) .0, 0.08000 = C(16) TO N(17) 
REM   THERMSIM   END (DO NOT REMOVE THIS LINE) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
DISTANCE 1.220000 , 0.020000 = N(13) TO O(14) 
DISTANCE 1.220000 , 0.020000 = N(13) TO O(15) 
DISTANCE 1.450000 , 0.020000 = C(12) TO N(13) 
DISTANCE 1.390000 , 0.020000 = C(11) TO C(12) 
DISTANCE 1.360000 , 0.020000 = C(10) TO C(11) 
DISTANCE 1.390000 , 0.020000 = C(9) TO C(10) 
DISTANCE 1.370000 , 0.020000 = C(8) TO C(9) 
DISTANCE 1.400000 , 0.020000 = C(7) TO C(8) 
DISTANCE 1.410000 , 0.020000 = C(7) TO C(12) 
DISTANCE 1.370000 , 0.020000 = C(7) TO N(6) 
DISTANCE 1.400000 , 0.02000 = C(5) TO N(6) 
DISTANCE 1.720000 , 0.020000 = S(1) TO C(5) 
DISTANCE 1.720000 , 0.020000 = S(1) TO C(2) 
DISTANCE 1.350000 , 0.020000 = C(2) TO C(3) 
DISTANCE 1.430000 , 0.020000 = C(3) TO C(4) 
DISTANCE 1.360000 , 0.020000 = C(4) TO C(5) 
DISTANCE 1.430000 , 0.020000 = C(4) TO C(16) 
DISTANCE 1.140000 , 0.020000 = C(16) TO N(17) 
DISTANCE 1.500000 , 0.020000 = C(2) TO C(18) 
END                  

#Restraints used for hydrogen refinement
#LIST 16
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 3) to H(31) 
REST 0.021, 0.002 = H(31,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(31) TO C ( 3) TO C(2) 
CONT H(31) TO C ( 3) TO C(4) 
PLANAR C ( 3) C(2) C(4) H(31) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 8) to H(81) 
REST 0.026, 0.002 = H(81,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(81) TO C ( 8) TO C(7) 
CONT H(81) TO C ( 8) TO C(9) 
PLANAR C ( 8) C(7) C(9) H(81) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 9) to H(91) 
REST 0.031, 0.002 = H(91,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(91) TO C ( 9) TO C(8) 
CONT H(91) TO C ( 9) TO C(10) 
PLANAR C ( 9) C(8) C(10) H(91) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 10) to H(101) 
REST 0.032, 0.002 = H(101,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(101) TO C ( 10) TO C(9) 
CONT H(101) TO C ( 10) TO C(11) 
PLANAR C ( 10) C(9) C(11) H(101) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 11) to H(111) 
REST 0.029, 0.002 = H(111,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(111) TO C ( 11) TO C(10) 
CONT H(111) TO C ( 11) TO C(12) 
PLANAR C ( 11) C(10) C(12) H(111) 
REM            3 H on sp 3
DIST 0.96, 0.02 = 
CONT C ( 18) to H(183) 
CONT C ( 18) to H(182) 
CONT C ( 18) to H(181) 
REST 0.032, 0.002 = H(183,U[ISO]) 
REST 0.032, 0.002 = H(182,U[ISO]) 
REST 0.032, 0.002 = H(181,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(2) to C ( 18) to H(183) 
CONT C(2) to C ( 18) to H(182) 
CONT C(2) to C ( 18) to H(181) 
ANGLE 0.0, 2.0 = mean H(183) to C ( 18) to H(182) 
CONT H(183) to C ( 18) to H(181) 
CONT H(182) to C ( 18) to H(181) 
REM            H1-N-R2
DIST 0.86, 0.02 = 
CONT N ( 6) to H(61) 
REST 0.022, 0.002 = H(61,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(61) TO N ( 6) TO C(5) 
CONT H(61) TO N ( 6) TO C(7) 
PLANAR 0.010000  C(5) C(7) N(6) H(61) 
END
;
_chemical_name_common            ROY
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_Y_30K
_database_code_depnum_ccdc_archive 'CCDC 1058328'
_audit_update_record             
;
2015-04-07 deposited with the CCDC.
2015-05-20 downloaded from the CCDC.
;
_audit_creation_date             15-02-27
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'ROY Y-form, 30 K'
_chemical_name_systematic        
5-methyl-2-((2-nitrophenyl)amino)-3-thiophenecarbonitrile


_refine_special_details          
; 
CheckCif alerts

PLAT921_ALERT_1_B R1  in the CIF and FCF Differ by ...............    -0.0071 Check 
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......     51.637 Check 

Crystals labels omitted reflections with several different flags that describe 
the reason for their omission. PLATON does not recognise this format and 
these omitted reflections have been included in the calculation of R1 and K.


RADNW01_ALERT_1_C  The radiation wavelength lies outside the expected range
            for the supplied radiation type. Expected range 0.71065-0.71075
            Wavelength given =    0.68890
PLAT092_ALERT_4_G Check: Wavelength given is not Cu,Ga,Mo,Ag Ka ..     0.6889 Ang.  
PLAT984_ALERT_1_G The  N-f'=     0.004 Deviates from the B&C-Value      0.006 Check 
PLAT984_ALERT_1_G The  O-f'=     0.007 Deviates from the B&C-Value      0.010 Check 
PLAT984_ALERT_1_G The  S-f'=     0.105 Deviates from the B&C-Value      0.119 Check 
            
These data have been collected using synchrotron radiation. The anomalous scattering 
factors for all elements were updated accordingly.
            
            
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......      0.974 Note  
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          8 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        382 Note

No action taken. The data are >98.5% complete above 0.85 Angstroms. Resolution and 
completeness statistics are given below.

#====================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#====================================================
Theta sin(th)/Lambda Complete  Expected Measured  Missing
#-------------------------------------------------------------------------------
 20.15     0.500     1.000         1188     1188        0
 22.27     0.550     0.999         1587     1585        2
 24.41     0.600     0.996         2062     2054        8
------------------------------------------------------------ ACTA Min. Res. ---
 26.60     0.650     0.989         2607     2578       29
 28.83     0.700     0.976         3273     3196       77
 31.11     0.750     0.953         4010     3821      189
 31.85     0.766     0.909         4280     3890      390


PLAT758_ALERT_4_C D-H..A  Calc      129.00, Rep   129.41(4) ......  Senseless su    
              N6   -H61  -O15     1.555   1.555   1.555      #         44       

No action taken              


PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do ! 

These are given at the end of the file


PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report

The molecular structure is known. H61 is bonded to a non-carbon atom (N6) but the 
data are not of sufficient quality to permit free refinement. All H atoms have been 
refined using the procedure described in:
Cooper, R. I., Thompson, A. L. & Watkin, D. J. (2010). J. Appl. Cryst. ,43,
1100-1107.
;



_cell_length_a                   8.45062(16)
_cell_length_b                   15.9403(3)
_cell_length_c                   8.46555(13)
_cell_angle_alpha                90
_cell_angle_beta                 91.0663(17)
_cell_angle_gamma                90
_cell_volume                     1140.16(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-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 0.0020 0.0020 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
and D. T. Cromer, J. Appl. Cryst. (1983), 16, 433.
;
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
and D. T. Cromer, J. Appl. Cryst. (1983), 16, 433.
;
N 0.0040 0.0030 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
and D. T. Cromer, J. Appl. Cryst. (1983), 16, 433.
;
O 0.0070 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
and D. T. Cromer, J. Appl. Cryst. (1983), 16, 433.
;
S 0.1050 0.1160 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
and D. T. Cromer, J. Appl. Cryst. (1983), 16, 433.
;

_cell_formula_units_Z            4

# Given Formula = C12 H9 N3 O2 S1 
# Dc =      1.51 Fooo =    536.00 Mu =      2.80 M =    259.29
# Found Formula = C12 H9 N3 O2 S1 
# Dc =      1.51 FOOO =    536.00 Mu =      2.80 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    4386
_cell_measurement_theta_min      2
_cell_measurement_theta_max      31
_cell_measurement_temperature    30

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_max          0.100

_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.280

# Sheldrick geometric approximatio 0.99 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  Synchrotron
_diffrn_measurement_device       Synchrotron
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.68890
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       Rigaku
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'User-defined model'
_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      30
_diffrn_reflns_number            15136
_reflns_number_total             3890
_diffrn_reflns_av_R_equivalents  0.053
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 3890 
# Theoretical number of reflections is about 8589 


_diffrn_reflns_theta_min         2.477
_diffrn_reflns_theta_max         31.854
_diffrn_measured_fraction_theta_max 0.907

_diffrn_reflns_theta_full        25.164
_diffrn_measured_fraction_theta_full 0.974


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              23
_reflns_limit_l_min              0
_reflns_limit_l_max              12

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.47
_refine_diff_density_max         0.55


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


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         3881
_refine_ls_number_restraints     0
_refine_ls_number_parameters     163
_oxford_refine_ls_R_factor_ref   0.0543
_refine_ls_wR_factor_ref         0.1033
_refine_ls_goodness_of_fit_ref   0.9081
_refine_ls_shift/su_max          0.0002658
_refine_ls_shift/su_mean         0.0000296


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3881
_refine_ls_R_factor_all          0.0543
_refine_ls_wR_factor_all         0.1033

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3291
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_gt          0.0962

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 1.48P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;


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 0.79100(4) 0.38451(2) 0.11294(4) 0.0082 1.0000 Uani . . . . . .
C2 C 0.98418(17) 0.35161(8) 0.08679(16) 0.0088 1.0000 Uani . . . . . .
C3 C 1.03870(17) 0.30731(8) 0.21429(16) 0.0088 1.0000 Uani . . . . . .
C4 C 0.92274(17) 0.29906(8) 0.33387(16) 0.0086 1.0000 Uani . . . . . .
C5 C 0.78122(17) 0.33796(8) 0.29635(16) 0.0081 1.0000 Uani . . . . . .
C7 C 0.63175(17) 0.39143(8) 0.51873(16) 0.0079 1.0000 Uani . . . . . .
C8 C 0.76438(17) 0.43559(9) 0.57958(16) 0.0095 1.0000 Uani . . . . . .
C9 C 0.75324(18) 0.48753(9) 0.70955(17) 0.0112 1.0000 Uani . . . . . .
C10 C 0.61085(18) 0.49763(9) 0.78783(17) 0.0116 1.0000 Uani . . . . . .
C11 C 0.47964(18) 0.45456(9) 0.73288(16) 0.0105 1.0000 Uani . . . . . .
C12 C 0.48913(16) 0.40250(8) 0.60034(16) 0.0081 1.0000 Uani . . . . . .
C16 C 0.94411(16) 0.25467(9) 0.47972(17) 0.0096 1.0000 Uani . . . . . .
C18 C 1.06696(18) 0.37093(9) -0.06333(17) 0.0114 1.0000 Uani . . . . . .
N6 N 0.64460(14) 0.34190(7) 0.38619(14) 0.0084 1.0000 Uani . . . . . .
N13 N 0.34141(15) 0.36338(7) 0.54782(14) 0.0091 1.0000 Uani . . . . . .
N17 N 0.95583(15) 0.21875(8) 0.59770(16) 0.0130 1.0000 Uani . . . . . .
O14 O 0.21835(13) 0.38166(7) 0.61574(13) 0.0141 1.0000 Uani . . . . . .
O15 O 0.34383(13) 0.31374(7) 0.43534(12) 0.0112 1.0000 Uani . . . . . .
H31 H 1.1414 0.2838 0.2226 0.0102 1.0000 Uiso R . . . . .
H81 H 0.8618 0.4295 0.5282 0.0125 1.0000 Uiso R . . . . .
H91 H 0.8445 0.5180 0.7453 0.0127 1.0000 Uiso R . . . . .
H101 H 0.6036 0.5342 0.8767 0.0148 1.0000 Uiso R . . . . .
H111 H 0.3826 0.4603 0.7835 0.0126 1.0000 Uiso R . . . . .
H181 H 1.1737 0.3500 -0.0567 0.0179 1.0000 Uiso R . . . . .
H182 H 1.0713 0.4302 -0.0830 0.0176 1.0000 Uiso R . . . . .
H183 H 1.0119 0.3445 -0.1525 0.0170 1.0000 Uiso R . . . . .
H61 H 0.5578 0.3235 0.3435 0.0114 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.00790(16) 0.00968(14) 0.00686(15) 0.00111(11) -0.00030(11) 0.00128(11)
C2 0.0083(6) 0.0092(5) 0.0091(6) -0.0005(4) -0.0004(5) 0.0003(4)
C3 0.0073(6) 0.0101(5) 0.0090(6) 0.0000(4) -0.0013(5) 0.0002(4)
C4 0.0095(6) 0.0089(5) 0.0074(5) 0.0003(4) -0.0011(5) -0.0006(4)
C5 0.0091(6) 0.0091(5) 0.0059(5) 0.0009(4) 0.0002(5) -0.0003(4)
C7 0.0100(6) 0.0069(5) 0.0068(5) 0.0010(4) -0.0011(5) 0.0007(4)
C8 0.0090(6) 0.0104(6) 0.0090(6) -0.0006(4) -0.0001(5) -0.0002(4)
C9 0.0131(7) 0.0102(6) 0.0102(6) -0.0004(5) -0.0038(5) -0.0003(5)
C10 0.0158(7) 0.0107(6) 0.0082(6) -0.0011(5) -0.0013(5) 0.0017(5)
C11 0.0134(7) 0.0101(6) 0.0080(6) 0.0007(4) 0.0006(5) 0.0026(5)
C12 0.0081(6) 0.0090(5) 0.0072(5) 0.0002(4) -0.0004(5) 0.0002(4)
C16 0.0062(6) 0.0117(6) 0.0108(6) -0.0003(5) -0.0003(5) 0.0004(4)
C18 0.0119(7) 0.0127(6) 0.0095(6) 0.0014(5) 0.0016(5) 0.0000(5)
N6 0.0069(5) 0.0106(5) 0.0075(5) -0.0020(4) -0.0006(4) -0.0002(4)
N13 0.0092(6) 0.0097(5) 0.0084(5) 0.0017(4) 0.0008(4) 0.0001(4)
N17 0.0096(6) 0.0158(6) 0.0135(6) 0.0028(5) -0.0004(5) 0.0008(4)
O14 0.0097(5) 0.0188(5) 0.0140(5) -0.0010(4) 0.0056(4) 0.0000(4)
O15 0.0102(5) 0.0135(5) 0.0098(5) -0.0032(4) -0.0004(4) 0.0002(4)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.93(8)
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 . C2 . 1.7327(15) yes
S1 . C5 . 1.7242(14) yes
C2 . C3 . 1.3630(18) yes
C2 . C18 . 1.494(2) yes
C3 . C4 . 1.428(2) yes
C3 . H31 . 0.947 no
C4 . C5 . 1.3790(19) yes
C4 . C16 . 1.4315(19) yes
C5 . N6 . 1.3957(19) yes
C7 . C8 . 1.4126(18) yes
C7 . C12 . 1.411(2) yes
C7 . N6 . 1.3779(17) yes
C8 . C9 . 1.3816(19) yes
C8 . H81 . 0.943 no
C9 . C10 . 1.394(2) yes
C9 . H91 . 0.956 no
C10 . C11 . 1.378(2) yes
C10 . H101 . 0.955 no
C11 . C12 . 1.3990(19) yes
C11 . H111 . 0.937 no
C12 . N13 . 1.4575(18) yes
C16 . N17 . 1.1539(19) yes
C18 . H181 . 0.963 no
C18 . H182 . 0.960 no
C18 . H183 . 0.975 no
N6 . H61 . 0.863 no
N13 . O14 . 1.2325(17) yes
N13 . O15 . 1.2385(15) yes
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
C2 . S1 . C5 . 92.63(7) yes
S1 . C2 . C3 . 111.16(11) yes
S1 . C2 . C18 . 120.23(10) yes
C3 . C2 . C18 . 128.58(13) yes
C2 . C3 . C4 . 112.51(13) yes
C2 . C3 . H31 . 124.1 no
C4 . C3 . H31 . 123.4 no
C3 . C4 . C5 . 113.51(12) yes
C3 . C4 . C16 . 125.43(13) yes
C5 . C4 . C16 . 121.06(13) yes
S1 . C5 . C4 . 110.18(11) yes
S1 . C5 . N6 . 121.69(10) yes
C4 . C5 . N6 . 128.12(12) yes
C8 . C7 . C12 . 115.99(12) yes
C8 . C7 . N6 . 120.56(13) yes
C12 . C7 . N6 . 123.45(12) yes
C7 . C8 . C9 . 121.58(14) yes
C7 . C8 . H81 . 118.3 no
C9 . C8 . H81 . 120.1 no
C8 . C9 . C10 . 121.34(13) yes
C8 . C9 . H91 . 119.4 no
C10 . C9 . H91 . 119.3 no
C9 . C10 . C11 . 118.58(13) yes
C9 . C10 . H101 . 121.0 no
C11 . C10 . H101 . 120.5 no
C10 . C11 . C12 . 120.57(14) yes
C10 . C11 . H111 . 120.2 no
C12 . C11 . H111 . 119.2 no
C7 . C12 . C11 . 121.94(13) yes
C7 . C12 . N13 . 122.11(12) yes
C11 . C12 . N13 . 115.90(13) yes
C4 . C16 . N17 . 177.67(15) yes
C2 . C18 . H181 . 109.4 no
C2 . C18 . H182 . 111.7 no
H181 . C18 . H182 . 108.3 no
C2 . C18 . H183 . 110.2 no
H181 . C18 . H183 . 109.2 no
H182 . C18 . H183 . 108.1 no
C5 . N6 . C7 . 123.23(12) yes
C5 . N6 . H61 . 117.5 no
C7 . N6 . H61 . 117.2 no
C12 . N13 . O14 . 118.81(12) yes
C12 . N13 . O15 . 118.79(12) yes
O14 . N13 . O15 . 122.40(12) 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
C3 . H31 . O15 1_655 126.17(4) 0.947 2.506 3.159(2) yes
N6 . H61 . N17 4_454 140.14(5) 0.863 2.336 3.049(2) yes
N6 . H61 . O15 . 129.41(4) 0.863 1.988 2.622(2) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 27/02/15 at 16:15:02
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) H   ( 183,X'S) 
RIDE N   (   6,X'S) H   (  61,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 27/02/15 at 16:15:02
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_chemical_name_common            ROY
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_Y_4.03_GPa
_database_code_depnum_ccdc_archive 'CCDC 1058329'
_audit_update_record             
;
2015-04-07 deposited with the CCDC.
2015-05-20 downloaded from the CCDC.
;
_audit_creation_date             14-12-16
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'ROY_Y-form, 4.03 GPa'
_chemical_name_systematic        
5-methyl-2-((2-nitrophenyl)amino)-3-thiophenecarbonitrile


_exptl_special_details           
; 
The crystal was loaded in a Merrill-Bassett diamond anvil cell, using 4:1 
methanol:ethanol as a pressure-transmitting medium and ruby as a pressure 
marker. Pressure was measured before and after data collection and the average
of these - 4.03 GPa - was taken to be the experimental pressure.
;




_refine_special_details          
; 
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      18.53 Degree
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......      0.644 Note  
PLAT911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L=  0.588        551 Report
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5882
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0081 Ang.  
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large.       5.82 Why ? 
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          60 %     
PLAT960_ALERT_3_G Number of Intensities with I  <   - 2*sig(I) ...          3 Check

Much of reciprocal space is unmeasurable, owing to the body of the diamond 
anvil cell, leading to missing reflections, low completeness and poor statistics.
Data are 61.0% complete to 0.85 Angstroms. Resolution and completeness 
statistics are given below.

#====================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#====================================================
Theta sin(th)/Lambda Complete  Expected Measured  Missing
#-------------------------------------------------------------------------------
 20.82     0.500     0.674          984      663      321
 23.01     0.550     0.644         1299      837      462
 24.71     0.588     0.641         1533      982      551
------------------------------------------------------------ ACTA Min. Res. ---


PLAT921_ALERT_1_B R1  in the CIF and FCF Differ by ...............    -0.0124 Check 
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......     44.508 Check

Crystals labels omitted reflections with several different flags that describe 
the reason for their omission. PLATON does not recognise this format and 
these omitted reflections have been included in the calculation of R1 and K.


PLAT201_ALERT_2_A Isotropic non-H Atoms in Main Residue(s) .......         17 Report
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         18 Note  
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         18 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         64 Note

Owing to poor data quality, only the relatively electron-rich sulfur atom could be 
refined anisotropically. Distance, vibration and thermal similarity restraints were 
necessary for a stable refinement. Previous variable-pressure experiments on 
organic materials have shown that pressure has little effect on covalent bond 
lengths and so the model has been restrained to the values observed at ambient 
pressure. The refinement procedure is discussed above and the restraints used 
are given at the end of this file.


PLAT157_ALERT_4_C Non-standard Monoclinic Beta Angle less 90 Deg        88.75 Degree
PLAT158_ALERT_4_G The Input Unitcell is NOT Standard/Reduced .....     Please Check

The unit cell settings are intended to be consistent across the pressure series, over which
the beta angle decreases from >90 to <90 degrees.


PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do ! 

These are given further below.


PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check 
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check 

This is correct.


PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C18 Check 

No action taken - the orientation is the same as other structures in the pressure series.


PLAT432_ALERT_2_G Short Inter X...Y Contact  S1     ..  C10     ..       3.27 Ang.  
And 7 similar alerts
  
Short contacts are not unusual for high-pressure structures.
;


_cell_length_a                   7.9246(16)
_cell_length_b                   14.028(3)
_cell_length_c                   8.4897(17)
_cell_angle_alpha                90
_cell_angle_beta                 88.75(3)
_cell_angle_gamma                90
_cell_volume                     943.5(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-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 =      1.83 Fooo =    536.00 Mu =      3.39 M =    259.29
# Found Formula = C12 H9 N3 O2 S1 
# Dc =      1.83 FOOO =    536.00 Mu =      3.39 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    1790
_cell_measurement_theta_min      3
_cell_measurement_theta_max      24
_cell_measurement_temperature    293

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_max          0.153

_exptl_crystal_density_diffrn    1.825
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.339

# Sheldrick geometric approximatio 0.97 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.49
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ


_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'User-defined model'
_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         4.03 #GPa
_diffrn_reflns_number            5729
_reflns_number_total             982
_diffrn_reflns_av_R_equivalents  0.050
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 982 
# Theoretical number of reflections is about 3218 


_diffrn_reflns_theta_min         2.805
_diffrn_reflns_theta_max         24.712
_diffrn_measured_fraction_theta_max 0.610

_diffrn_reflns_theta_full        18.534
_diffrn_measured_fraction_theta_full 0.644


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_reflns_limit_h_min              -8
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              15
_reflns_limit_l_min              0
_reflns_limit_l_max              8

_oxford_diffrn_Wilson_B_factor   1.23
_oxford_diffrn_Wilson_scale      28.59

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

_refine_diff_density_min         -0.66
_refine_diff_density_max         0.61


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>0.0\s(I)
_refine_ls_number_reflns         975
_refine_ls_number_restraints     64
_refine_ls_number_parameters     78
_oxford_refine_ls_R_factor_ref   0.0739
_refine_ls_wR_factor_ref         0.1161
_refine_ls_goodness_of_fit_ref   0.9767
_refine_ls_shift/su_max          0.0001484
_refine_ls_shift/su_mean         0.0000153


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        976
_refine_ls_R_factor_all          0.0743
_refine_ls_wR_factor_all         0.1166

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                759
_refine_ls_R_factor_gt           0.0557
_refine_ls_wR_factor_gt          0.1055

_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.00P)² + 5.82P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

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


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 0.82602(19) 0.38144(9) 0.1078(2) 0.0170 1.0000 Uani D U . . . .
C2 C 1.0288(7) 0.3386(3) 0.0792(7) 0.0153(9) 1.0000 Uiso D U . . . .
C3 C 1.0862(7) 0.2962(3) 0.2080(7) 0.0159(9) 1.0000 Uiso D U . . . .
C4 C 0.9665(7) 0.2978(3) 0.3369(7) 0.0164(8) 1.0000 Uiso D U . . . .
C5 C 0.8199(7) 0.3425(3) 0.2996(7) 0.0161(8) 1.0000 Uiso D U . . . .
C7 C 0.6639(7) 0.3985(3) 0.5344(7) 0.0151(8) 1.0000 Uiso D U . . . .
C8 C 0.8075(7) 0.4337(3) 0.6047(7) 0.0171(9) 1.0000 Uiso D U . . . .
C9 C 0.8007(8) 0.4809(3) 0.7461(8) 0.0211(10) 1.0000 Uiso D U . . . .
C10 C 0.6447(7) 0.4969(3) 0.8229(8) 0.0209(10) 1.0000 Uiso D U . . . .
C11 C 0.5033(7) 0.4625(3) 0.7589(7) 0.0178(9) 1.0000 Uiso D U . . . .
C12 C 0.5096(7) 0.4140(3) 0.6161(7) 0.0156(8) 1.0000 Uiso D U . . . .
C16 C 0.9866(7) 0.2534(3) 0.4840(7) 0.0175(9) 1.0000 Uiso D U . . . .
C18 C 1.1108(7) 0.3576(3) -0.0786(7) 0.0164(10) 1.0000 Uiso D U . . . .
N6 N 0.6715(6) 0.3560(3) 0.3890(6) 0.0155(8) 1.0000 Uiso D U . . . .
N13 N 0.3518(6) 0.3828(3) 0.5537(6) 0.0173(8) 1.0000 Uiso D U . . . .
N17 N 0.9926(6) 0.2165(3) 0.6048(6) 0.0217(10) 1.0000 Uiso D U . . . .
O14 O 0.2197(5) 0.4109(2) 0.6179(5) 0.0230(8) 1.0000 Uiso D U . . . .
O15 O 0.3497(5) 0.3308(2) 0.4367(5) 0.0250(9) 1.0000 Uiso D U . . . .
H31 H 1.1917 0.2685 0.2151 0.0193 1.0000 Uiso R . . . . .
H61 H 0.5810 0.3363 0.3488 0.0195 1.0000 Uiso R . . . . .
H81 H 0.9109 0.4257 0.5520 0.0208 1.0000 Uiso R . . . . .
H91 H 0.9005 0.5036 0.7890 0.0250 1.0000 Uiso R . . . . .
H101 H 0.6401 0.5316 0.9170 0.0249 1.0000 Uiso R . . . . .
H111 H 0.3998 0.4711 0.8105 0.0211 1.0000 Uiso R . . . . .
H181 H 1.2234 0.3314 -0.0835 0.0252 1.0000 Uiso R . . . . .
H182 H 1.1146 0.4245 -0.0998 0.0245 1.0000 Uiso R . . . . .
H183 H 1.0458 0.3267 -0.1590 0.0248 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0146(9) 0.0213(8) 0.0151(11) 0.0015(5) -0.0006(9) 0.0022(5)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.1931(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 . C2 . 1.728(5) yes
S1 . C5 . 1.718(6) yes
C2 . C3 . 1.333(8) yes
C2 . C18 . 1.500(6) yes
C3 . C4 . 1.433(6) yes
C3 . H31 . 0.925 no
C4 . C5 . 1.363(8) yes
C4 . C16 . 1.408(8) yes
C5 . N6 . 1.398(5) yes
C7 . C8 . 1.387(8) yes
C7 . C12 . 1.410(6) yes
C7 . N6 . 1.371(7) yes
C8 . C9 . 1.372(8) yes
C8 . H81 . 0.931 no
C9 . C10 . 1.403(7) yes
C9 . H91 . 0.934 no
C10 . C11 . 1.345(8) yes
C10 . H101 . 0.936 no
C11 . C12 . 1.390(8) yes
C11 . H111 . 0.929 no
C12 . N13 . 1.437(7) yes
C16 . N17 . 1.150(7) yes
C18 . H181 . 0.965 no
C18 . H182 . 0.955 no
C18 . H183 . 0.966 no
N6 . H61 . 0.847 no
N13 . O14 . 1.234(5) yes
N13 . O15 . 1.233(6) yes
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
C2 . S1 . C5 . 91.7(3) yes
S1 . C2 . C3 . 111.9(4) yes
S1 . C2 . C18 . 116.5(4) yes
C3 . C2 . C18 . 131.5(5) yes
C2 . C3 . C4 . 112.8(5) yes
C2 . C3 . H31 . 124.4 no
C4 . C3 . H31 . 122.8 no
C3 . C4 . C5 . 112.6(5) yes
C3 . C4 . C16 . 125.7(5) yes
C5 . C4 . C16 . 121.5(4) yes
S1 . C5 . C4 . 111.1(3) yes
S1 . C5 . N6 . 118.5(5) yes
C4 . C5 . N6 . 130.3(5) yes
C8 . C7 . C12 . 116.4(5) yes
C8 . C7 . N6 . 121.4(4) yes
C12 . C7 . N6 . 122.0(6) yes
C7 . C8 . C9 . 122.1(5) yes
C7 . C8 . H81 . 118.1 no
C9 . C8 . H81 . 119.7 no
C8 . C9 . C10 . 120.1(6) yes
C8 . C9 . H91 . 119.2 no
C10 . C9 . H91 . 120.6 no
C9 . C10 . C11 . 119.2(6) yes
C9 . C10 . H101 . 119.8 no
C11 . C10 . H101 . 121.0 no
C10 . C11 . C12 . 120.9(5) yes
C10 . C11 . H111 . 119.8 no
C12 . C11 . H111 . 119.3 no
C7 . C12 . C11 . 121.2(5) yes
C7 . C12 . N13 . 121.7(5) yes
C11 . C12 . N13 . 117.1(4) yes
C4 . C16 . N17 . 175.8(6) yes
C2 . C18 . H181 . 110.6 no
C2 . C18 . H182 . 110.7 no
H181 . C18 . H182 . 110.0 no
C2 . C18 . H183 . 108.8 no
H181 . C18 . H183 . 107.8 no
H182 . C18 . H183 . 108.8 no
C5 . N6 . C7 . 124.6(5) yes
C5 . N6 . H61 . 116.5 no
C7 . N6 . H61 . 118.9 no
C12 . N13 . O14 . 118.5(5) yes
C12 . N13 . O15 . 120.2(4) yes
O14 . N13 . O15 . 121.2(5) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 16/12/14 at 16:45:18
#
#Refinement with riding constraints on H atoms
#LIST     12                                                                    
BLOCK SCALE X'S, 
CONT S(1,U'S) 
CONT C(2,U[ISO]) UNTIL O(15) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  18,X'S) H   ( 183,X'S) H   ( 182,X'S) H   ( 181,X'S) 
RIDE N   (   6,X'S) H   (  61,X'S) 
END           

#Refinement of hydrogen positions and U[iso] with restraints
#LIST 12
block
CONT H(   31 ,X,Y,Z,U[ISO])
CONT H(   81 ,X,Y,Z,U[ISO])
CONT H(   91 ,X,Y,Z,U[ISO])
CONT H(  101 ,X,Y,Z,U[ISO])
CONT H(  111 ,X,Y,Z,U[ISO])
CONT H(  183 ,X,Y,Z,U[ISO])
CONT H(  182 ,X,Y,Z,U[ISO])
CONT H(  181 ,X,Y,Z,U[ISO])
CONT H(   61 ,X,Y,Z,U[ISO])
END
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 16/12/14 at 16:45:18
#
#Non-H atom restraints
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
REM   DELU   START (DO NOT REMOVE THIS LINE) 
VIBR .0, 0.00200 = S(1) TO C(2) 
VIBR .0, 0.00200 = S(1) TO C(5) 
VIBR .0, 0.00500 = C(5) TO C(2) 
VIBR .0, 0.00200 = C(2) TO C(18) 
VIBR .0, 0.00200 = C(2) TO C(3) 
VIBR .0, 0.00500 = C(18) TO S(1) 
VIBR .0, 0.00500 = C(3) TO S(1) 
VIBR .0, 0.00500 = C(3) TO C(18) 
VIBR .0, 0.00200 = C(3) TO C(4) 
VIBR .0, 0.00500 = C(4) TO C(2) 
VIBR .0, 0.00200 = C(4) TO C(5) 
VIBR .0, 0.00200 = C(4) TO C(16) 
VIBR .0, 0.00500 = C(5) TO C(3) 
VIBR .0, 0.00500 = C(16) TO C(3) 
VIBR .0, 0.00500 = C(16) TO C(5) 
VIBR .0, 0.00200 = C(5) TO N(6) 
VIBR .0, 0.00500 = S(1) TO C(4) 
VIBR .0, 0.00500 = N(6) TO C(4) 
VIBR .0, 0.00500 = N(6) TO S(1) 
VIBR .0, 0.00200 = N(6) TO C(7) 
VIBR .0, 0.00500 = C(7) TO C(5) 
VIBR .0, 0.00200 = C(7) TO C(8) 
VIBR .0, 0.00200 = C(7) TO C(12) 
VIBR .0, 0.00500 = C(8) TO N(6) 
VIBR .0, 0.00500 = C(12) TO N(6) 
VIBR .0, 0.00500 = C(12) TO C(8) 
VIBR .0, 0.00200 = C(8) TO C(9) 
VIBR .0, 0.00500 = C(9) TO C(7) 
VIBR .0, 0.00200 = C(9) TO C(10) 
VIBR .0, 0.00500 = C(10) TO C(8) 
VIBR .0, 0.00200 = C(10) TO C(11) 
VIBR .0, 0.00500 = C(11) TO C(9) 
VIBR .0, 0.00200 = C(11) TO C(12) 
VIBR .0, 0.00500 = C(12) TO C(10) 
VIBR .0, 0.00200 = C(12) TO N(13) 
VIBR .0, 0.00500 = C(7) TO C(11) 
VIBR .0, 0.00500 = N(13) TO C(11) 
VIBR .0, 0.00500 = N(13) TO C(7) 
VIBR .0, 0.00200 = N(13) TO O(14) 
VIBR .0, 0.00200 = N(13) TO O(15) 
VIBR .0, 0.00500 = O(14) TO C(12) 
VIBR .0, 0.00500 = O(15) TO C(12) 
VIBR .0, 0.00500 = O(15) TO O(14) 
VIBR .0, 0.00200 = C(16) TO N(17) 
VIBR .0, 0.00500 = N(17) TO C(4) 
REM   DELU   END (DO NOT REMOVE THIS LINE) 
REM   THERMSIM   START (DO NOT REMOVE THIS LINE) 
U(IJ) .0, 0.04000 = S(1) TO C(2) 
U(IJ) .0, 0.04000 = S(1) TO C(5) 
U(IJ) .0, 0.08000 = C(2) TO C(18) 
U(IJ) .0, 0.04000 = C(2) TO C(3) 
U(IJ) .0, 0.04000 = C(3) TO C(4) 
U(IJ) .0, 0.04000 = C(4) TO C(5) 
U(IJ) .0, 0.04000 = C(4) TO C(16) 
U(IJ) .0, 0.04000 = C(5) TO N(6) 
U(IJ) .0, 0.04000 = N(6) TO C(7) 
U(IJ) .0, 0.04000 = C(7) TO C(8) 
U(IJ) .0, 0.04000 = C(7) TO C(12) 
U(IJ) .0, 0.04000 = C(8) TO C(9) 
U(IJ) .0, 0.04000 = C(9) TO C(10) 
U(IJ) .0, 0.04000 = C(10) TO C(11) 
U(IJ) .0, 0.04000 = C(11) TO C(12) 
U(IJ) .0, 0.04000 = C(12) TO N(13) 
U(IJ) .0, 0.08000 = N(13) TO O(14) 
U(IJ) .0, 0.08000 = N(13) TO O(15) 
U(IJ) .0, 0.08000 = C(16) TO N(17) 
REM   THERMSIM   END (DO NOT REMOVE THIS LINE) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
DISTANCE 1.220000 , 0.020000 = N(13) TO O(14) 
DISTANCE 1.220000 , 0.020000 = N(13) TO O(15) 
DISTANCE 1.450000 , 0.020000 = C(12) TO N(13) 
DISTANCE 1.390000 , 0.020000 = C(11) TO C(12) 
DISTANCE 1.360000 , 0.020000 = C(10) TO C(11) 
DISTANCE 1.390000 , 0.020000 = C(9) TO C(10) 
DISTANCE 1.370000 , 0.020000 = C(8) TO C(9) 
DISTANCE 1.400000 , 0.020000 = C(7) TO C(8) 
DISTANCE 1.410000 , 0.020000 = C(7) TO C(12) 
DISTANCE 1.370000 , 0.020000 = C(7) TO N(6) 
DISTANCE 1.400000 , 0.02000 = C(5) TO N(6) 
DISTANCE 1.720000 , 0.020000 = S(1) TO C(5) 
DISTANCE 1.720000 , 0.020000 = S(1) TO C(2) 
DISTANCE 1.350000 , 0.020000 = C(2) TO C(3) 
DISTANCE 1.430000 , 0.020000 = C(3) TO C(4) 
DISTANCE 1.360000 , 0.020000 = C(4) TO C(5) 
DISTANCE 1.430000 , 0.020000 = C(4) TO C(16) 
DISTANCE 1.140000 , 0.020000 = C(16) TO N(17) 
DISTANCE 1.500000 , 0.020000 = C(2) TO C(18) 
END              

#Restraints used for hydrogen refinement
#LIST 16
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 3) to H(31) 
REST 0.019, 0.002 = H(31,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(31) TO C ( 3) TO C(2) 
CONT H(31) TO C ( 3) TO C(4) 
PLANAR C ( 3) C(2) C(4) H(31) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 8) to H(81) 
REST 0.021, 0.002 = H(81,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(81) TO C ( 8) TO C(7) 
CONT H(81) TO C ( 8) TO C(9) 
PLANAR C ( 8) C(7) C(9) H(81) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 9) to H(91) 
REST 0.025, 0.002 = H(91,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(91) TO C ( 9) TO C(8) 
CONT H(91) TO C ( 9) TO C(10) 
PLANAR C ( 9) C(8) C(10) H(91) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 10) to H(101) 
REST 0.025, 0.002 = H(101,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(101) TO C ( 10) TO C(9) 
CONT H(101) TO C ( 10) TO C(11) 
PLANAR C ( 10) C(9) C(11) H(101) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 11) to H(111) 
REST 0.021, 0.002 = H(111,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(111) TO C ( 11) TO C(10) 
CONT H(111) TO C ( 11) TO C(12) 
PLANAR C ( 11) C(10) C(12) H(111) 
REM            3 H on sp 3
DIST 0.96, 0.02 = 
CONT C ( 18) to H(183) 
CONT C ( 18) to H(182) 
CONT C ( 18) to H(181) 
REST 0.025, 0.002 = H(183,U[ISO]) 
REST 0.025, 0.002 = H(182,U[ISO]) 
REST 0.025, 0.002 = H(181,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(2) to C ( 18) to H(183) 
CONT C(2) to C ( 18) to H(182) 
CONT C(2) to C ( 18) to H(181) 
ANGLE 0.0, 2.0 = mean H(183) to C ( 18) to H(182) 
CONT H(183) to C ( 18) to H(181) 
CONT H(182) to C ( 18) to H(181) 
REM            H1-N-R2
DIST 0.86, 0.02 = 
CONT N ( 6) to H(61) 
REST 0.019, 0.002 = H(61,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(61) TO N ( 6) TO C(5) 
CONT H(61) TO N ( 6) TO C(7) 
PLANAR 0.010000  C(5) C(7) N(6) H(61) 
END
;
_chemical_name_common            ROY
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_Y_5.20_GPa
_database_code_depnum_ccdc_archive 'CCDC 1058330'
_audit_update_record             
;
2015-04-07 deposited with the CCDC.
2015-05-20 downloaded from the CCDC.
;
_audit_creation_date             14-12-16
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'ROY_Y-form, 5.20 GPa'
_chemical_name_systematic        
5-methyl-2-((2-nitrophenyl)amino)-3-thiophenecarbonitrile


_exptl_special_details           
; 
The crystal was loaded in a Merrill-Bassett diamond anvil cell, using 4:1 
methanol:ethanol as a pressure-transmitting medium and ruby as a pressure 
marker. Pressure was measured before and after data collection and the average
of these - 5.20 GPa - was taken to be the experimental pressure.
;


_refine_special_details          
; 
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      18.53 Degree
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......      0.636 Note  
PLAT340_ALERT_3_B Low Bond Precision on  C-C Bonds ...............     0.0103 Ang.  
PLAT911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L=  0.588        486 Report
THETM01_ALERT_3_C  The value of sine(theta_max)/wavelength is less than 0.590
            Calculated sin(theta_max)/wavelength =    0.5880
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large.       6.31 Why ? 
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          45 %     
PLAT952_ALERT_5_G Calculated (ThMax) and CIF-Reported Lmax Differ           2 Units 
PLAT958_ALERT_1_G Calculated (ThMax) and Actual (FCF) Lmax Differ           2 Units 
PLAT960_ALERT_3_G Number of Intensities with I  <   - 2*sig(I) ...          3 Check 

Much of reciprocal space is unmeasurable, owing to the body of the diamond 
anvil cell, leading to missing reflections, low completeness and poor statistics.
Data are 60.4% complete to 0.85 Angstroms. Resolution and completeness 
statistics are given below.

#====================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#====================================================
Theta sin(th)/Lambda Complete  Expected Measured  Missing
#-------------------------------------------------------------------------------
 20.82     0.500     0.671          933      626      307
 23.01     0.550     0.665         1208      803      405
 24.70     0.588     0.659         1424      938      486
------------------------------------------------------------ ACTA Min. Res. ---


PLAT921_ALERT_1_B R1  in the CIF and FCF Differ by ...............    -0.0130 Check 
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......     50.783 Check 

Crystals labels omitted reflections with several different flags that describe 
the reason for their omission. PLATON does not recognise this format and 
these omitted reflections have been included in the calculation of R1 and K.


PLAT201_ALERT_2_A Isotropic non-H Atoms in Main Residue(s) .......         17 Report
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         18 Note  
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         18 Report
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         64 Note  

Owing to poor data quality, only the relatively electron-rich sulfur atom could be 
refined anisotropically. Distance, vibration and thermal similarity restraints were 
necessary for a stable refinement. Previous variable-pressure experiments on 
organic materials have shown that pressure has little effect on covalent bond 
lengths and so the model has been restrained to the values observed at ambient 
pressure. The refinement procedure is discussed above and the restraints used 
are given at the end of this file.


PLAT157_ALERT_4_C Non-standard Monoclinic Beta Angle less 90 Deg        88.55 Degree
PLAT158_ALERT_4_G The Input Unitcell is NOT Standard/Reduced .....     Please Check

The unit cell settings are intended to be consistent across the pressure series, over which
the beta angle decreases from >90 to <90 degrees.


PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do ! 

These are given further below.


PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check 
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check 

This is correct.


PLAT432_ALERT_2_G Short Inter X...Y Contact  S1     ..  C10     ..       3.21 Ang.  
And 9 similar alerts

Short contacts are not unusual for high-pressure structures.
;


_cell_length_a                   7.8626(16)
_cell_length_b                   13.721(3)
_cell_length_c                   8.4707(17)
_cell_angle_alpha                90
_cell_angle_beta                 88.55(3)
_cell_angle_gamma                90
_cell_volume                     913.5(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-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 =      1.89 Fooo =    536.00 Mu =      3.50 M =    259.29
# Found Formula = C12 H9 N3 O2 S1 
# Dc =      1.89 FOOO =    536.00 Mu =      3.50 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    1328
_cell_measurement_theta_min      3
_cell_measurement_theta_max      24
_cell_measurement_temperature    293

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_max          0.153

_exptl_crystal_density_diffrn    1.885
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.350

# Sheldrick geometric approximatio 0.97 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ


_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'User-defined model'
_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         5.20 #GPa
_diffrn_reflns_number            5470
_reflns_number_total             938
_diffrn_reflns_av_R_equivalents  0.077
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 938 
# Theoretical number of reflections is about 3112 


_diffrn_reflns_theta_min         2.827
_diffrn_reflns_theta_max         24.703
_diffrn_measured_fraction_theta_max 0.604

_diffrn_reflns_theta_full        18.527
_diffrn_measured_fraction_theta_full 0.636


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_reflns_limit_h_min              -9
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              15
_reflns_limit_l_min              0
_reflns_limit_l_max              7

_oxford_diffrn_Wilson_B_factor   1.42
_oxford_diffrn_Wilson_scale      4.19

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

_refine_diff_density_min         -0.70
_refine_diff_density_max         0.75


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>0.0\s(I)
_refine_ls_number_reflns         931
_refine_ls_number_restraints     64
_refine_ls_number_parameters     78
_oxford_refine_ls_R_factor_ref   0.0990
_refine_ls_wR_factor_ref         0.1644
_refine_ls_goodness_of_fit_ref   0.9690
_refine_ls_shift/su_max          0.0001206
_refine_ls_shift/su_mean         0.0000116


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        931
_refine_ls_R_factor_all          0.0990
_refine_ls_wR_factor_all         0.1644

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                668
_refine_ls_R_factor_gt           0.0692
_refine_ls_wR_factor_gt          0.1408

_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 6.31P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

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


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 0.8279(2) 0.38055(11) 0.1063(3) 0.0203 1.0000 Uani D U . . . .
C2 C 1.0317(8) 0.3364(4) 0.0773(9) 0.0168(10) 1.0000 Uiso D U . . . .
C3 C 1.0901(8) 0.2961(4) 0.2071(9) 0.0171(11) 1.0000 Uiso D U . . . .
C4 C 0.9714(8) 0.2983(4) 0.3363(9) 0.0182(10) 1.0000 Uiso D U . . . .
C5 C 0.8224(8) 0.3431(4) 0.2991(9) 0.0191(10) 1.0000 Uiso D U . . . .
C7 C 0.6666(8) 0.3985(4) 0.5354(10) 0.0178(10) 1.0000 Uiso D U . . . .
C8 C 0.8103(9) 0.4341(4) 0.6064(10) 0.0191(11) 1.0000 Uiso D U . . . .
C9 C 0.8020(9) 0.4802(4) 0.7505(10) 0.0223(12) 1.0000 Uiso D U . . . .
C10 C 0.6465(9) 0.4960(5) 0.8267(10) 0.0240(12) 1.0000 Uiso D U . . . .
C11 C 0.5038(9) 0.4627(4) 0.7601(10) 0.0210(11) 1.0000 Uiso D U . . . .
C12 C 0.5104(8) 0.4146(4) 0.6157(10) 0.0200(10) 1.0000 Uiso D U . . . .
C16 C 0.9905(9) 0.2532(4) 0.4850(10) 0.0189(11) 1.0000 Uiso D U . . . .
C18 C 1.1155(9) 0.3569(4) -0.0792(10) 0.0180(12) 1.0000 Uiso D U . . . .
N6 N 0.6739(7) 0.3582(3) 0.3880(8) 0.0181(10) 1.0000 Uiso D U . . . .
N13 N 0.3511(7) 0.3842(4) 0.5535(8) 0.0219(10) 1.0000 Uiso D U . . . .
N17 N 0.9935(7) 0.2159(4) 0.6060(9) 0.0233(12) 1.0000 Uiso D U . . . .
O14 O 0.2191(6) 0.4119(3) 0.6197(7) 0.0239(10) 1.0000 Uiso D U . . . .
O15 O 0.3494(6) 0.3321(3) 0.4346(7) 0.0274(11) 1.0000 Uiso D U . . . .
H31 H 1.1980 0.2684 0.2141 0.0198 1.0000 Uiso R . . . . .
H61 H 0.5804 0.3399 0.3467 0.0222 1.0000 Uiso R . . . . .
H81 H 0.9153 0.4268 0.5546 0.0228 1.0000 Uiso R . . . . .
H91 H 0.9025 0.5026 0.7955 0.0270 1.0000 Uiso R . . . . .
H101 H 0.6401 0.5295 0.9232 0.0290 1.0000 Uiso R . . . . .
H111 H 0.4007 0.4714 0.8116 0.0249 1.0000 Uiso R . . . . .
H181 H 1.2254 0.3268 -0.0844 0.0272 1.0000 Uiso R . . . . .
H182 H 1.1271 0.4259 -0.0931 0.0270 1.0000 Uiso R . . . . .
H183 H 1.0455 0.3309 -0.1606 0.0269 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0184(10) 0.0214(9) 0.0209(15) 0.0021(8) 0.0007(11) 0.0020(7)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.501(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . C2 . 1.725(6) yes
S1 . C5 . 1.712(8) yes
C2 . C3 . 1.323(10) yes
C2 . C18 . 1.492(9) yes
C3 . C4 . 1.421(8) yes
C3 . H31 . 0.933 no
C4 . C5 . 1.367(9) yes
C4 . C16 . 1.415(10) yes
C5 . N6 . 1.388(7) yes
C7 . C8 . 1.383(10) yes
C7 . C12 . 1.406(8) yes
C7 . N6 . 1.365(9) yes
C8 . C9 . 1.375(10) yes
C8 . H81 . 0.930 no
C9 . C10 . 1.384(8) yes
C9 . H91 . 0.938 no
C10 . C11 . 1.348(10) yes
C10 . H101 . 0.939 no
C11 . C12 . 1.389(10) yes
C11 . H111 . 0.919 no
C12 . N13 . 1.433(9) yes
C16 . N17 . 1.147(9) yes
C18 . H181 . 0.958 no
C18 . H182 . 0.958 no
C18 . H183 . 0.962 no
N6 . H61 . 0.860 no
N13 . O14 . 1.227(6) yes
N13 . O15 . 1.235(8) yes
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
C2 . S1 . C5 . 91.8(3) yes
S1 . C2 . C3 . 111.7(5) yes
S1 . C2 . C18 . 116.6(6) yes
C3 . C2 . C18 . 131.5(6) yes
C2 . C3 . C4 . 113.3(6) yes
C2 . C3 . H31 . 123.9 no
C4 . C3 . H31 . 122.7 no
C3 . C4 . C5 . 112.5(7) yes
C3 . C4 . C16 . 126.4(6) yes
C5 . C4 . C16 . 120.8(5) yes
S1 . C5 . C4 . 110.7(5) yes
S1 . C5 . N6 . 118.3(6) yes
C4 . C5 . N6 . 131.0(7) yes
C8 . C7 . C12 . 116.6(7) yes
C8 . C7 . N6 . 121.6(5) yes
C12 . C7 . N6 . 121.5(7) yes
C7 . C8 . C9 . 121.8(6) yes
C7 . C8 . H81 . 118.8 no
C9 . C8 . H81 . 119.4 no
C8 . C9 . C10 . 120.5(8) yes
C8 . C9 . H91 . 119.3 no
C10 . C9 . H91 . 120.2 no
C9 . C10 . C11 . 119.1(8) yes
C9 . C10 . H101 . 120.7 no
C11 . C10 . H101 . 120.2 no
C10 . C11 . C12 . 121.1(6) yes
C10 . C11 . H111 . 119.4 no
C12 . C11 . H111 . 119.5 no
C7 . C12 . C11 . 120.9(7) yes
C7 . C12 . N13 . 122.5(7) yes
C11 . C12 . N13 . 116.7(5) yes
C4 . C16 . N17 . 175.1(8) yes
C2 . C18 . H181 . 109.7 no
C2 . C18 . H182 . 109.5 no
H181 . C18 . H182 . 109.8 no
C2 . C18 . H183 . 108.6 no
H181 . C18 . H183 . 109.8 no
H182 . C18 . H183 . 109.4 no
C5 . N6 . C7 . 124.9(7) yes
C5 . N6 . H61 . 116.9 no
C7 . N6 . H61 . 118.2 no
C12 . N13 . O14 . 118.6(6) yes
C12 . N13 . O15 . 119.7(5) yes
O14 . N13 . O15 . 121.7(7) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 16/12/14 at 16:48:17
#
#Refinement with riding constraints on H atoms
#LIST     12                                                                    
BLOCK SCALE X'S, 
CONT S(1,U'S) 
CONT C(2,U[ISO]) UNTIL O(15) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  18,X'S) H   ( 183,X'S) H   ( 182,X'S) H   ( 181,X'S) 
RIDE N   (   6,X'S) H   (  61,X'S) 
END

#Refinement of hydrogen positions and U[iso] with restraints
#LIST 12
block
CONT H(   31 ,X,Y,Z,U[ISO])
CONT H(   81 ,X,Y,Z,U[ISO])
CONT H(   91 ,X,Y,Z,U[ISO])
CONT H(  101 ,X,Y,Z,U[ISO])
CONT H(  111 ,X,Y,Z,U[ISO])
CONT H(  183 ,X,Y,Z,U[ISO])
CONT H(  182 ,X,Y,Z,U[ISO])
CONT H(  181 ,X,Y,Z,U[ISO])
CONT H(   61 ,X,Y,Z,U[ISO])
END
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 16/12/14 at 16:48:17
#
#Non-H atom restraints
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
REM   DELU   START (DO NOT REMOVE THIS LINE) 
VIBR .0, 0.00200 = S(1) TO C(2) 
VIBR .0, 0.00200 = S(1) TO C(5) 
VIBR .0, 0.00500 = C(5) TO C(2) 
VIBR .0, 0.00200 = C(2) TO C(18) 
VIBR .0, 0.00200 = C(2) TO C(3) 
VIBR .0, 0.00500 = C(18) TO S(1) 
VIBR .0, 0.00500 = C(3) TO S(1) 
VIBR .0, 0.00500 = C(3) TO C(18) 
VIBR .0, 0.00200 = C(3) TO C(4) 
VIBR .0, 0.00500 = C(4) TO C(2) 
VIBR .0, 0.00200 = C(4) TO C(5) 
VIBR .0, 0.00200 = C(4) TO C(16) 
VIBR .0, 0.00500 = C(5) TO C(3) 
VIBR .0, 0.00500 = C(16) TO C(3) 
VIBR .0, 0.00500 = C(16) TO C(5) 
VIBR .0, 0.00200 = C(5) TO N(6) 
VIBR .0, 0.00500 = S(1) TO C(4) 
VIBR .0, 0.00500 = N(6) TO C(4) 
VIBR .0, 0.00500 = N(6) TO S(1) 
VIBR .0, 0.00200 = N(6) TO C(7) 
VIBR .0, 0.00500 = C(7) TO C(5) 
VIBR .0, 0.00200 = C(7) TO C(8) 
VIBR .0, 0.00200 = C(7) TO C(12) 
VIBR .0, 0.00500 = C(8) TO N(6) 
VIBR .0, 0.00500 = C(12) TO N(6) 
VIBR .0, 0.00500 = C(12) TO C(8) 
VIBR .0, 0.00200 = C(8) TO C(9) 
VIBR .0, 0.00500 = C(9) TO C(7) 
VIBR .0, 0.00200 = C(9) TO C(10) 
VIBR .0, 0.00500 = C(10) TO C(8) 
VIBR .0, 0.00200 = C(10) TO C(11) 
VIBR .0, 0.00500 = C(11) TO C(9) 
VIBR .0, 0.00200 = C(11) TO C(12) 
VIBR .0, 0.00500 = C(12) TO C(10) 
VIBR .0, 0.00200 = C(12) TO N(13) 
VIBR .0, 0.00500 = C(7) TO C(11) 
VIBR .0, 0.00500 = N(13) TO C(11) 
VIBR .0, 0.00500 = N(13) TO C(7) 
VIBR .0, 0.00200 = N(13) TO O(14) 
VIBR .0, 0.00200 = N(13) TO O(15) 
VIBR .0, 0.00500 = O(14) TO C(12) 
VIBR .0, 0.00500 = O(15) TO C(12) 
VIBR .0, 0.00500 = O(15) TO O(14) 
VIBR .0, 0.00200 = C(16) TO N(17) 
VIBR .0, 0.00500 = N(17) TO C(4) 
REM   DELU   END (DO NOT REMOVE THIS LINE) 
REM   THERMSIM   START (DO NOT REMOVE THIS LINE) 
U(IJ) .0, 0.04000 = S(1) TO C(2) 
U(IJ) .0, 0.04000 = S(1) TO C(5) 
U(IJ) .0, 0.08000 = C(2) TO C(18) 
U(IJ) .0, 0.04000 = C(2) TO C(3) 
U(IJ) .0, 0.04000 = C(3) TO C(4) 
U(IJ) .0, 0.04000 = C(4) TO C(5) 
U(IJ) .0, 0.04000 = C(4) TO C(16) 
U(IJ) .0, 0.04000 = C(5) TO N(6) 
U(IJ) .0, 0.04000 = N(6) TO C(7) 
U(IJ) .0, 0.04000 = C(7) TO C(8) 
U(IJ) .0, 0.04000 = C(7) TO C(12) 
U(IJ) .0, 0.04000 = C(8) TO C(9) 
U(IJ) .0, 0.04000 = C(9) TO C(10) 
U(IJ) .0, 0.04000 = C(10) TO C(11) 
U(IJ) .0, 0.04000 = C(11) TO C(12) 
U(IJ) .0, 0.04000 = C(12) TO N(13) 
U(IJ) .0, 0.08000 = N(13) TO O(14) 
U(IJ) .0, 0.08000 = N(13) TO O(15) 
U(IJ) .0, 0.08000 = C(16) TO N(17) 
REM   THERMSIM   END (DO NOT REMOVE THIS LINE) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
DISTANCE 1.220000 , 0.020000 = N(13) TO O(14) 
DISTANCE 1.220000 , 0.020000 = N(13) TO O(15) 
DISTANCE 1.450000 , 0.020000 = C(12) TO N(13) 
DISTANCE 1.390000 , 0.020000 = C(11) TO C(12) 
DISTANCE 1.360000 , 0.020000 = C(10) TO C(11) 
DISTANCE 1.390000 , 0.020000 = C(9) TO C(10) 
DISTANCE 1.370000 , 0.020000 = C(8) TO C(9) 
DISTANCE 1.400000 , 0.020000 = C(7) TO C(8) 
DISTANCE 1.410000 , 0.020000 = C(7) TO C(12) 
DISTANCE 1.370000 , 0.020000 = C(7) TO N(6) 
DISTANCE 1.400000 , 0.02000 = C(5) TO N(6) 
DISTANCE 1.720000 , 0.020000 = S(1) TO C(5) 
DISTANCE 1.720000 , 0.020000 = S(1) TO C(2) 
DISTANCE 1.350000 , 0.020000 = C(2) TO C(3) 
DISTANCE 1.430000 , 0.020000 = C(3) TO C(4) 
DISTANCE 1.360000 , 0.020000 = C(4) TO C(5) 
DISTANCE 1.430000 , 0.020000 = C(4) TO C(16) 
DISTANCE 1.140000 , 0.020000 = C(16) TO N(17) 
DISTANCE 1.500000 , 0.020000 = C(2) TO C(18) 
END      

#Restraints used for hydrogen refinement
#LIST 16
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 3) to H(31) 
REST 0.020, 0.002 = H(31,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(31) TO C ( 3) TO C(2) 
CONT H(31) TO C ( 3) TO C(4) 
PLANAR C ( 3) C(2) C(4) H(31) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 8) to H(81) 
REST 0.023, 0.002 = H(81,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(81) TO C ( 8) TO C(7) 
CONT H(81) TO C ( 8) TO C(9) 
PLANAR C ( 8) C(7) C(9) H(81) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 9) to H(91) 
REST 0.027, 0.002 = H(91,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(91) TO C ( 9) TO C(8) 
CONT H(91) TO C ( 9) TO C(10) 
PLANAR C ( 9) C(8) C(10) H(91) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 10) to H(101) 
REST 0.029, 0.002 = H(101,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(101) TO C ( 10) TO C(9) 
CONT H(101) TO C ( 10) TO C(11) 
PLANAR C ( 10) C(9) C(11) H(101) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 11) to H(111) 
REST 0.025, 0.002 = H(111,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(111) TO C ( 11) TO C(10) 
CONT H(111) TO C ( 11) TO C(12) 
PLANAR C ( 11) C(10) C(12) H(111) 
REM            3 H on sp 3
DIST 0.96, 0.02 = 
CONT C ( 18) to H(183) 
CONT C ( 18) to H(182) 
CONT C ( 18) to H(181) 
REST 0.027, 0.002 = H(183,U[ISO]) 
REST 0.027, 0.002 = H(182,U[ISO]) 
REST 0.027, 0.002 = H(181,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(2) to C ( 18) to H(183) 
CONT C(2) to C ( 18) to H(182) 
CONT C(2) to C ( 18) to H(181) 
ANGLE 0.0, 2.0 = mean H(183) to C ( 18) to H(182) 
CONT H(183) to C ( 18) to H(181) 
CONT H(182) to C ( 18) to H(181) 
REM            H1-N-R2
DIST 0.86, 0.02 = 
CONT N ( 6) to H(61) 
REST 0.022, 0.002 = H(61,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(61) TO N ( 6) TO C(5) 
CONT H(61) TO N ( 6) TO C(7) 
PLANAR 0.010000  C(5) C(7) N(6) H(61) 
END
;
_chemical_name_common            ROY
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_Y_ambient
_database_code_depnum_ccdc_archive 'CCDC 1058331'
_audit_update_record             
;
2015-04-07 deposited with the CCDC.
2015-05-20 downloaded from the CCDC.
;
_audit_creation_date             14-12-16
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'ROY Y-form, ambient pressure'
_chemical_name_systematic        
5-methyl-2-((2-nitrophenyl)amino)-3-thiophenecarbonitrile



_refine_special_details          
; 
CheckCif alerts

PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......      0.945 Note  
PLAT910_ALERT_3_G Missing # of FCF Reflections Below Th(Min) .....          3 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        401 Note  
PLAT960_ALERT_3_G Number of Intensities with I  <   - 2*sig(I) ...          7 Check 

No action taken. The data are >98.5% complete above 0.85 Angstroms. Resolution and 
completeness statistics are given below.

#==================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#==================================================
Theta sin(th)/Lambda Complete  Expected Measured  Missing
#-------------------------------------------------------------------------------
 20.82     0.500     0.997         1253     1249        4
 23.01     0.550     0.997         1659     1654        5
 25.24     0.600     0.998         2159     2155        4
------------------------------------------------------------ ACTA Min. Res. ---
 27.51     0.650     0.977         2713     2650       63
 29.65     0.696     0.874         3231     2825      406


PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report

The molecular structure is known. H61 is bonded to a non-carbon atom (N6) but the 
data are not of sufficient quality to permit free refinement. All H atoms have been 
refined using the procedure described in:
Cooper, R. I., Thompson, A. L. & Watkin, D. J. (2010). J. Appl. Cryst. ,43,
1100-1107. 
 

PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do ! 

These are given at the end of the file. 


PLAT158_ALERT_4_G The Input Unitcell is NOT Standard/Reduced .....     Please Check

The reported unit cell has been selected so space group assignment is consistent 
with the literature and that all structures across the pressure series reported in 
the manuscript are comparable.

PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check 
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check 

This is correct
;


_cell_length_a                   8.5322(17)
_cell_length_b                   16.412(3)
_cell_length_c                   8.4958(17)
_cell_angle_alpha                90
_cell_angle_beta                 91.78(3)
_cell_angle_gamma                90
_cell_volume                     1189.1(4)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-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 =      2.69 M =    259.29
# Found Formula = C12 H9 N3 O2 S1 
# Dc =      1.45 FOOO =    536.00 Mu =      2.69 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    2475
_cell_measurement_theta_min      4
_cell_measurement_theta_max      28
_cell_measurement_temperature    293

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.106
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_max          0.235

_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.269

# Sheldrick geometric approximatio 0.96 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.97
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'User-defined model'
_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            5816
_reflns_number_total             2826
_diffrn_reflns_av_R_equivalents  0.023
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2826 
# Theoretical number of reflections is about 6719 


_diffrn_reflns_theta_min         3.333
_diffrn_reflns_theta_max         29.650
_diffrn_measured_fraction_theta_max 0.845

_diffrn_reflns_theta_full        25.203
_diffrn_measured_fraction_theta_full 0.945


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_reflns_limit_h_min              -10
_reflns_limit_h_max              10
_reflns_limit_k_min              0
_reflns_limit_k_max              22
_reflns_limit_l_min              0
_reflns_limit_l_max              10

_oxford_diffrn_Wilson_B_factor   3.15
_oxford_diffrn_Wilson_scale      5.89

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

_refine_diff_density_min         -0.30
_refine_diff_density_max         0.33


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         2825
_refine_ls_number_restraints     0
_refine_ls_number_parameters     163
_oxford_refine_ls_R_factor_ref   0.0587
_refine_ls_wR_factor_ref         0.1074
_refine_ls_goodness_of_fit_ref   0.9671
_refine_ls_shift/su_max          0.0002834
_refine_ls_shift/su_mean         0.0000297


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2826
_refine_ls_R_factor_all          0.0589
_refine_ls_wR_factor_all         0.1076

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2174
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_gt          0.0976

_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.66P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;


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 0.79283(6) 0.38555(3) 0.11890(6) 0.0424 1.0000 Uani . . . . . .
C2 C 0.9818(2) 0.35186(12) 0.0941(2) 0.0383 1.0000 Uani . . . . . .
C3 C 1.0342(2) 0.30776(12) 0.2186(2) 0.0392 1.0000 Uani . . . . . .
C4 C 0.9196(2) 0.29975(12) 0.3374(2) 0.0364 1.0000 Uani . . . . . .
C5 C 0.7827(2) 0.33896(11) 0.2997(2) 0.0351 1.0000 Uani . . . . . .
C7 C 0.6354(2) 0.39262(11) 0.5184(2) 0.0358 1.0000 Uani . . . . . .
C8 C 0.7648(3) 0.43728(13) 0.5760(2) 0.0483 1.0000 Uani . . . . . .
C9 C 0.7543(3) 0.48842(14) 0.7035(3) 0.0615 1.0000 Uani . . . . . .
C10 C 0.6154(4) 0.49656(16) 0.7817(3) 0.0666 1.0000 Uani . . . . . .
C11 C 0.4874(3) 0.45359(15) 0.7308(2) 0.0569 1.0000 Uani . . . . . .
C12 C 0.4954(2) 0.40248(12) 0.6009(2) 0.0408 1.0000 Uani . . . . . .
C16 C 0.9409(2) 0.25441(14) 0.4801(2) 0.0464 1.0000 Uani . . . . . .
C18 C 1.0645(3) 0.37133(15) -0.0549(2) 0.0536 1.0000 Uani . . . . . .
N6 N 0.64734(18) 0.34374(10) 0.38816(17) 0.0385 1.0000 Uani . . . . . .
N13 N 0.3514(2) 0.36202(12) 0.5515(2) 0.0494 1.0000 Uani . . . . . .
N17 N 0.9533(2) 0.21867(15) 0.5947(2) 0.0682 1.0000 Uani . . . . . .
O14 O 0.2327(2) 0.37521(15) 0.6246(3) 0.0924 1.0000 Uani . . . . . .
O15 O 0.34996(17) 0.31677(11) 0.43758(19) 0.0585 1.0000 Uani . . . . . .
H31 H 1.1348 0.2847 0.2267 0.0471 1.0000 Uiso R . . . . .
H81 H 0.8613 0.4324 0.5255 0.0571 1.0000 Uiso R . . . . .
H91 H 0.8449 0.5169 0.7335 0.0733 1.0000 Uiso R . . . . .
H101 H 0.6076 0.5315 0.8685 0.0799 1.0000 Uiso R . . . . .
H111 H 0.3896 0.4584 0.7804 0.0680 1.0000 Uiso R . . . . .
H183 H 1.1682 0.3513 -0.0493 0.0800 1.0000 Uiso R . . . . .
H182 H 1.0672 0.4285 -0.0735 0.0799 1.0000 Uiso R . . . . .
H181 H 1.0073 0.3460 -0.1437 0.0803 1.0000 Uiso R . . . . .
H61 H 0.5643 0.3222 0.3519 0.0459 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0438(3) 0.0472(3) 0.0364(3) 0.0076(2) 0.00189(18) 0.0080(2)
C2 0.0388(10) 0.0405(10) 0.0359(9) 0.0009(8) 0.0045(7) -0.0012(8)
C3 0.0337(9) 0.0430(11) 0.0408(10) -0.0009(8) 0.0021(7) 0.0009(8)
C4 0.0361(9) 0.0408(10) 0.0321(9) 0.0023(8) -0.0010(7) -0.0016(8)
C5 0.0357(9) 0.0379(10) 0.0318(9) -0.0015(8) 0.0018(7) -0.0019(8)
C7 0.0449(10) 0.0328(9) 0.0295(9) 0.0028(7) -0.0022(7) 0.0054(8)
C8 0.0539(12) 0.0449(12) 0.0455(11) -0.0037(9) -0.0064(9) -0.0006(10)
C9 0.0832(18) 0.0468(13) 0.0530(13) -0.0087(11) -0.0213(12) -0.0008(12)
C10 0.104(2) 0.0545(15) 0.0411(12) -0.0120(11) -0.0058(12) 0.0229(15)
C11 0.0797(17) 0.0549(14) 0.0363(11) 0.0025(10) 0.0075(10) 0.0213(13)
C12 0.0516(11) 0.0397(11) 0.0312(9) 0.0070(8) 0.0044(8) 0.0081(9)
C16 0.0351(10) 0.0595(13) 0.0445(11) 0.0099(10) 0.0000(8) 0.0022(9)
C18 0.0559(13) 0.0607(14) 0.0449(12) 0.0101(10) 0.0146(9) 0.0035(11)
N6 0.0342(8) 0.0447(9) 0.0367(8) -0.0078(7) 0.0012(6) -0.0032(7)
N13 0.0466(10) 0.0575(11) 0.0447(10) 0.0115(9) 0.0123(8) 0.0063(9)
N17 0.0535(11) 0.0930(17) 0.0578(12) 0.0354(12) -0.0004(9) 0.0064(11)
O14 0.0648(12) 0.1230(19) 0.0921(14) -0.0126(13) 0.0455(11) -0.0103(12)
O15 0.0434(8) 0.0753(12) 0.0568(9) -0.0061(8) 0.0021(7) -0.0034(8)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.4431(8)
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 . C2 . 1.724(2) yes
S1 . C5 . 1.7204(18) yes
C2 . C3 . 1.347(3) yes
C2 . C18 . 1.502(3) yes
C3 . C4 . 1.433(3) yes
C3 . H31 . 0.939 no
C4 . C5 . 1.363(3) yes
C4 . C16 . 1.429(3) yes
C5 . N6 . 1.399(2) yes
C7 . C8 . 1.401(3) yes
C7 . C12 . 1.413(3) yes
C7 . N6 . 1.373(2) yes
C8 . C9 . 1.375(3) yes
C8 . H81 . 0.943 no
C9 . C10 . 1.384(4) yes
C9 . H91 . 0.932 no
C10 . C11 . 1.359(4) yes
C10 . H101 . 0.937 no
C11 . C12 . 1.390(3) yes
C11 . H111 . 0.950 no
C12 . N13 . 1.447(3) yes
C16 . N17 . 1.139(3) yes
C18 . H183 . 0.943 no
C18 . H182 . 0.952 no
C18 . H181 . 0.979 no
N6 . H61 . 0.841 no
N13 . O14 . 1.224(2) yes
N13 . O15 . 1.219(2) yes
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
C2 . S1 . C5 . 92.30(9) yes
S1 . C2 . C3 . 111.40(14) yes
S1 . C2 . C18 . 120.03(15) yes
C3 . C2 . C18 . 128.55(18) yes
C2 . C3 . C4 . 112.68(17) yes
C2 . C3 . H31 . 123.7 no
C4 . C3 . H31 . 123.7 no
C3 . C4 . C5 . 112.96(16) yes
C3 . C4 . C16 . 124.97(17) yes
C5 . C4 . C16 . 122.05(17) yes
S1 . C5 . C4 . 110.66(13) yes
S1 . C5 . N6 . 121.33(14) yes
C4 . C5 . N6 . 128.01(17) yes
C8 . C7 . C12 . 115.87(18) yes
C8 . C7 . N6 . 120.65(17) yes
C12 . C7 . N6 . 123.47(17) yes
C7 . C8 . C9 . 121.6(2) yes
C7 . C8 . H81 . 119.1 no
C9 . C8 . H81 . 119.3 no
C8 . C9 . C10 . 121.0(2) yes
C8 . C9 . H91 . 116.6 no
C10 . C9 . H91 . 122.4 no
C9 . C10 . C11 . 119.3(2) yes
C9 . C10 . H101 . 121.3 no
C11 . C10 . H101 . 119.4 no
C10 . C11 . C12 . 120.5(2) yes
C10 . C11 . H111 . 121.6 no
C12 . C11 . H111 . 117.9 no
C7 . C12 . C11 . 121.7(2) yes
C7 . C12 . N13 . 121.77(17) yes
C11 . C12 . N13 . 116.46(19) yes
C4 . C16 . N17 . 177.9(2) yes
C2 . C18 . H183 . 110.4 no
C2 . C18 . H182 . 111.4 no
H183 . C18 . H182 . 108.9 no
C2 . C18 . H181 . 108.8 no
H183 . C18 . H181 . 109.6 no
H182 . C18 . H181 . 107.8 no
C5 . N6 . C7 . 123.28(16) yes
C5 . N6 . H61 . 118.6 no
C7 . N6 . H61 . 117.2 no
C12 . N13 . O14 . 118.7(2) yes
C12 . N13 . O15 . 119.85(16) yes
O14 . N13 . O15 . 121.5(2) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 16/12/14 at 13:20:48
#
#Refinement with riding constraints on H atoms
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  18,X'S) H   ( 183,X'S) H   ( 182,X'S) H   ( 181,X'S) 
RIDE N   (   6,X'S) H   (  61,X'S) 
END    

#Refinement of hydrogen positions and U[iso] with restraints
#LIST 12
block
CONT H(   31 ,X,Y,Z,U[ISO])
CONT H(   81 ,X,Y,Z,U[ISO])
CONT H(   91 ,X,Y,Z,U[ISO])
CONT H(  101 ,X,Y,Z,U[ISO])
CONT H(  111 ,X,Y,Z,U[ISO])
CONT H(  183 ,X,Y,Z,U[ISO])
CONT H(  182 ,X,Y,Z,U[ISO])
CONT H(  181 ,X,Y,Z,U[ISO])
CONT H(   61 ,X,Y,Z,U[ISO])
END
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 16/12/14 at 13:20:48
#
#Restraints used for hydrogen refinement
#LIST 16
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 3) to H(31) 
REST 0.047, 0.002 = H(31,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(31) TO C ( 3) TO C(2) 
CONT H(31) TO C ( 3) TO C(4) 
PLANAR C ( 3) C(2) C(4) H(31) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 8) to H(81) 
REST 0.058, 0.002 = H(81,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(81) TO C ( 8) TO C(7) 
CONT H(81) TO C ( 8) TO C(9) 
PLANAR C ( 8) C(7) C(9) H(81) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 9) to H(91) 
REST 0.074, 0.002 = H(91,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(91) TO C ( 9) TO C(8) 
CONT H(91) TO C ( 9) TO C(10) 
PLANAR C ( 9) C(8) C(10) H(91) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 10) to H(101) 
REST 0.080, 0.002 = H(101,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(101) TO C ( 10) TO C(9) 
CONT H(101) TO C ( 10) TO C(11) 
PLANAR C ( 10) C(9) C(11) H(101) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 11) to H(111) 
REST 0.068, 0.002 = H(111,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(111) TO C ( 11) TO C(10) 
CONT H(111) TO C ( 11) TO C(12) 
PLANAR C ( 11) C(10) C(12) H(111) 
REM            3 H on sp 3
DIST 0.96, 0.02 = 
CONT C ( 18) to H(183) 
CONT C ( 18) to H(182) 
CONT C ( 18) to H(181) 
REST 0.080, 0.002 = H(183,U[ISO]) 
REST 0.080, 0.002 = H(182,U[ISO]) 
REST 0.080, 0.002 = H(181,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(2) to C ( 18) to H(183) 
CONT C(2) to C ( 18) to H(182) 
CONT C(2) to C ( 18) to H(181) 
ANGLE 0.0, 2.0 = mean H(183) to C ( 18) to H(182) 
CONT H(183) to C ( 18) to H(181) 
CONT H(182) to C ( 18) to H(181) 
REM            H1-N-R2
DIST 0.86, 0.02 = 
CONT N ( 6) to H(61) 
REST 0.046, 0.002 = H(61,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(61) TO N ( 6) TO C(5) 
CONT H(61) TO N ( 6) TO C(7) 
PLANAR 0.010000  C(5) C(7) N(6) H(61) 
END
;
_chemical_name_common            ROY
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
####################################################################### 
# 
# 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_Y_recovered_ambient
_database_code_depnum_ccdc_archive 'CCDC 1058332'
_audit_update_record             
;
2015-04-07 deposited with the CCDC.
2015-05-20 downloaded from the CCDC.
;
_audit_creation_date             15-02-25
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'ROY Y-form, ambient pressure'
_chemical_name_systematic        
5-methyl-2-((2-nitrophenyl)amino)-3-thiophenecarbonitrile


_refine_special_details          
; 
CheckCif alerts

PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......      0.957 Note  
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        442 Note  
PLAT960_ALERT_3_G Number of Intensities with I  <   - 2*sig(I) ...          7 Check

No action taken. The data are >98.5% complete above 0.85 Angstroms. Resolution and 
completeness statistics are given below.

#======================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#======================================================
Theta sin(th)/Lambda Complete  Expected Measured  Missing
#-------------------------------------------------------------------------------
 20.82     0.500     0.997         1253     1249        4
 23.01     0.550     0.997         1659     1654        5
 25.24     0.600     0.998         2159     2155        4
------------------------------------------------------------ ACTA Min. Res. ---
 27.51     0.650     0.977         2713     2650       63
 29.65     0.696     0.874         3231     2825      406
 

PLAT921_ALERT_1_B R1  in the CIF and FCF Differ by ...............    -0.0170 Check 
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......    370.097 Check

Crystals labels omitted reflections with several different flags that describe 
the reason for their omission. PLATON does not recognise this format and 
these omitted reflections have been included in the calculation of R1 and K.


PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0042 Ang.  
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check

Noted, no action taken

 
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do ! 

These are given at the end of the file


PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report

The molecular structure is known. H61 is bonded to a non-carbon atom (N6) but the 
data are not of sufficient quality to permit free refinement. All H atoms have been 
refined using the procedure described in:
Cooper, R. I., Thompson, A. L. & Watkin, D. J. (2010). J. Appl. Cryst. ,43,
1100-1107. 


PLAT158_ALERT_4_G The Input Unitcell is NOT Standard/Reduced .....     Please Check

The reported unit cell has been selected so space group assignment is consistent 
with the literature and that all structures across the pressure series reported in 
the manuscript are comparable.


PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check 
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check 

This is correct
;


_cell_length_a                   8.5460(17)
_cell_length_b                   16.420(3)
_cell_length_c                   8.5053(17)
_cell_angle_alpha                90
_cell_angle_beta                 91.78(3)
_cell_angle_gamma                90
_cell_volume                     1193.0(4)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-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 =      1.44 Fooo =    536.00 Mu =      2.68 M =    259.29
# Found Formula = C12 H9 N3 O2 S1 
# Dc =      1.44 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    1725
_cell_measurement_theta_min      2
_cell_measurement_theta_max      27
_cell_measurement_temperature    293

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.044
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_max          0.152

_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_meas      ?
_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   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω/2θ

_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'User-defined model'
_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            5266
_reflns_number_total             2695
_diffrn_reflns_av_R_equivalents  0.025
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2695 
# Theoretical number of reflections is about 6259 


_diffrn_reflns_theta_min         2.481
_diffrn_reflns_theta_max         28.857
_diffrn_measured_fraction_theta_max 0.859

_diffrn_reflns_theta_full        25.106
_diffrn_measured_fraction_theta_full 0.957


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       11
_reflns_limit_h_min              -11
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              22
_reflns_limit_l_min              0
_reflns_limit_l_max              11

_oxford_diffrn_Wilson_B_factor   2.92
_oxford_diffrn_Wilson_scale      44.57

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

_refine_diff_density_min         -0.55
_refine_diff_density_max         0.44


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>0.0\s(I)
_refine_ls_number_reflns         2685
_refine_ls_number_restraints     0
_refine_ls_number_parameters     163
_oxford_refine_ls_R_factor_ref   0.0768
_refine_ls_wR_factor_ref         0.0899
_refine_ls_goodness_of_fit_ref   1.0366
_refine_ls_shift/su_max          0.0003211
_refine_ls_shift/su_mean         0.0000195


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2686
_refine_ls_R_factor_all          0.0770
_refine_ls_wR_factor_all         0.0901

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1846
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_gt          0.0729

_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.01P)² + 0.93P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;


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 0.79277(7) 0.38551(4) 0.11897(7) 0.0423 1.0000 Uani . . . . . .
C2 C 0.9823(3) 0.35205(14) 0.0944(3) 0.0372 1.0000 Uani . . . . . .
C3 C 1.0339(3) 0.30777(14) 0.2190(3) 0.0389 1.0000 Uani . . . . . .
C4 C 0.9198(3) 0.29972(14) 0.3367(3) 0.0355 1.0000 Uani . . . . . .
C5 C 0.7824(3) 0.33898(14) 0.2997(3) 0.0351 1.0000 Uani . . . . . .
C7 C 0.6356(3) 0.39267(14) 0.5184(2) 0.0351 1.0000 Uani . . . . . .
C8 C 0.7654(3) 0.43744(15) 0.5757(3) 0.0482 1.0000 Uani . . . . . .
C9 C 0.7544(4) 0.48853(17) 0.7033(3) 0.0619 1.0000 Uani . . . . . .
C10 C 0.6154(4) 0.49638(19) 0.7815(3) 0.0657 1.0000 Uani . . . . . .
C11 C 0.4875(4) 0.45362(17) 0.7304(3) 0.0556 1.0000 Uani . . . . . .
C12 C 0.4960(3) 0.40240(14) 0.6012(3) 0.0393 1.0000 Uani . . . . . .
C16 C 0.9409(3) 0.25482(16) 0.4802(3) 0.0454 1.0000 Uani . . . . . .
C18 C 1.0646(3) 0.37138(17) -0.0547(3) 0.0539 1.0000 Uani . . . . . .
N6 N 0.6472(2) 0.34383(12) 0.3881(2) 0.0387 1.0000 Uani . . . . . .
N13 N 0.3517(2) 0.36197(14) 0.5516(3) 0.0495 1.0000 Uani . . . . . .
N17 N 0.9531(3) 0.21866(16) 0.5946(3) 0.0672 1.0000 Uani . . . . . .
O14 O 0.2332(2) 0.37532(16) 0.6250(3) 0.0917 1.0000 Uani . . . . . .
O15 O 0.3501(2) 0.31669(12) 0.4375(2) 0.0577 1.0000 Uani . . . . . .
H31 H 1.1340 0.2849 0.2284 0.0471 1.0000 Uiso R . . . . .
H81 H 0.8600 0.4332 0.5246 0.0578 1.0000 Uiso R . . . . .
H91 H 0.8433 0.5176 0.7344 0.0732 1.0000 Uiso R . . . . .
H101 H 0.6100 0.5314 0.8682 0.0797 1.0000 Uiso R . . . . .
H111 H 0.3889 0.4600 0.7782 0.0680 1.0000 Uiso R . . . . .
H181 H 1.1661 0.3481 -0.0529 0.0803 1.0000 Uiso R . . . . .
H182 H 1.0741 0.4296 -0.0720 0.0801 1.0000 Uiso R . . . . .
H183 H 1.0067 0.3484 -0.1419 0.0798 1.0000 Uiso R . . . . .
H61 H 0.5646 0.3211 0.3530 0.0450 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0425(3) 0.0484(4) 0.0359(3) 0.0076(3) 0.0017(3) 0.0080(3)
C2 0.0364(13) 0.0401(13) 0.0353(13) -0.0016(11) 0.0038(10) -0.0006(11)
C3 0.0336(12) 0.0429(14) 0.0401(13) 0.0005(11) -0.0008(10) 0.0020(11)
C4 0.0334(12) 0.0407(13) 0.0323(12) 0.0023(10) -0.0015(10) 0.0000(11)
C5 0.0366(12) 0.0386(13) 0.0301(12) -0.0016(10) 0.0015(10) -0.0030(11)
C7 0.0451(14) 0.0328(12) 0.0271(11) 0.0021(10) -0.0020(10) 0.0046(11)
C8 0.0534(16) 0.0468(15) 0.0441(15) -0.0045(12) -0.0056(12) 0.0007(13)
C9 0.080(2) 0.0494(17) 0.0551(18) -0.0084(14) -0.0206(16) 0.0013(16)
C10 0.102(3) 0.0565(19) 0.0378(16) -0.0106(14) -0.0061(17) 0.0212(19)
C11 0.078(2) 0.0536(18) 0.0350(14) 0.0028(13) 0.0060(14) 0.0200(16)
C12 0.0489(15) 0.0400(14) 0.0291(12) 0.0061(10) 0.0027(10) 0.0090(12)
C16 0.0335(13) 0.0573(17) 0.0453(15) 0.0114(13) -0.0004(11) 0.0018(12)
C18 0.0570(17) 0.0628(19) 0.0426(15) 0.0094(13) 0.0149(13) 0.0022(14)
N6 0.0312(10) 0.0491(12) 0.0359(11) -0.0089(9) 0.0015(8) -0.0037(9)
N13 0.0463(13) 0.0587(15) 0.0441(13) 0.0127(11) 0.0125(10) 0.0052(11)
N17 0.0498(14) 0.093(2) 0.0582(16) 0.0349(15) -0.0002(12) 0.0049(14)
O14 0.0629(14) 0.124(2) 0.0912(17) -0.0099(15) 0.0460(13) -0.0077(14)
O15 0.0424(11) 0.0770(14) 0.0537(12) -0.0071(11) 0.0012(9) -0.0039(10)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.16638(8)
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 . C2 . 1.729(2) yes
S1 . C5 . 1.721(2) yes
C2 . C3 . 1.348(3) yes
C2 . C18 . 1.504(3) yes
C3 . C4 . 1.426(3) yes
C3 . H31 . 0.936 no
C4 . C5 . 1.367(3) yes
C4 . C16 . 1.433(3) yes
C5 . N6 . 1.400(3) yes
C7 . C8 . 1.405(3) yes
C7 . C12 . 1.413(3) yes
C7 . N6 . 1.374(3) yes
C8 . C9 . 1.377(4) yes
C8 . H81 . 0.933 no
C9 . C10 . 1.386(4) yes
C9 . H91 . 0.928 no
C10 . C11 . 1.360(4) yes
C10 . H101 . 0.937 no
C11 . C12 . 1.388(3) yes
C11 . H111 . 0.953 no
C12 . N13 . 1.451(3) yes
C16 . N17 . 1.142(3) yes
C18 . H181 . 0.947 no
C18 . H182 . 0.971 no
C18 . H183 . 0.956 no
N6 . H61 . 0.845 no
N13 . O14 . 1.226(3) yes
N13 . O15 . 1.223(3) yes
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
C2 . S1 . C5 . 92.35(12) yes
S1 . C2 . C3 . 111.19(18) yes
S1 . C2 . C18 . 119.96(18) yes
C3 . C2 . C18 . 128.8(2) yes
C2 . C3 . C4 . 112.8(2) yes
C2 . C3 . H31 . 124.0 no
C4 . C3 . H31 . 123.1 no
C3 . C4 . C5 . 113.3(2) yes
C3 . C4 . C16 . 125.1(2) yes
C5 . C4 . C16 . 121.6(2) yes
S1 . C5 . C4 . 110.33(17) yes
S1 . C5 . N6 . 121.36(17) yes
C4 . C5 . N6 . 128.3(2) yes
C8 . C7 . C12 . 116.0(2) yes
C8 . C7 . N6 . 120.6(2) yes
C12 . C7 . N6 . 123.5(2) yes
C7 . C8 . C9 . 121.3(3) yes
C7 . C8 . H81 . 119.1 no
C9 . C8 . H81 . 119.6 no
C8 . C9 . C10 . 121.0(3) yes
C8 . C9 . H91 . 117.6 no
C10 . C9 . H91 . 121.4 no
C9 . C10 . C11 . 119.4(3) yes
C9 . C10 . H101 . 120.0 no
C11 . C10 . H101 . 120.6 no
C10 . C11 . C12 . 120.3(3) yes
C10 . C11 . H111 . 121.4 no
C12 . C11 . H111 . 118.2 no
C7 . C12 . C11 . 121.9(2) yes
C7 . C12 . N13 . 121.8(2) yes
C11 . C12 . N13 . 116.3(2) yes
C4 . C16 . N17 . 178.0(3) yes
C2 . C18 . H181 . 110.7 no
C2 . C18 . H182 . 112.3 no
H181 . C18 . H182 . 108.6 no
C2 . C18 . H183 . 109.0 no
H181 . C18 . H183 . 107.8 no
H182 . C18 . H183 . 108.3 no
C5 . N6 . C7 . 123.24(19) yes
C5 . N6 . H61 . 118.6 no
C7 . N6 . H61 . 117.5 no
C12 . N13 . O14 . 118.6(2) yes
C12 . N13 . O15 . 119.8(2) yes
O14 . N13 . O15 . 121.6(2) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 25/02/15 at 11:40:15
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  18,X'S) H   ( 183,X'S) H   ( 182,X'S) H   ( 181,X'S) 
RIDE N   (   6,X'S) H   (  61,X'S) 
END                                                                             

#Refinement of hydrogen positions and U[iso] with restraints
#LIST 12
block
CONT H(   31 ,X,Y,Z,U[ISO])
CONT H(   81 ,X,Y,Z,U[ISO])
CONT H(   91 ,X,Y,Z,U[ISO])
CONT H(  101 ,X,Y,Z,U[ISO])
CONT H(  111 ,X,Y,Z,U[ISO])
CONT H(  183 ,X,Y,Z,U[ISO])
CONT H(  182 ,X,Y,Z,U[ISO])
CONT H(  181 ,X,Y,Z,U[ISO])
CONT H(   61 ,X,Y,Z,U[ISO])
END
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 16/12/14 at 13:20:48
#
#Restraints used for hydrogen refinement
#LIST 16
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 3) to H(31) 
REST 0.047, 0.002 = H(31,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(31) TO C ( 3) TO C(2) 
CONT H(31) TO C ( 3) TO C(4) 
PLANAR C ( 3) C(2) C(4) H(31) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 8) to H(81) 
REST 0.058, 0.002 = H(81,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(81) TO C ( 8) TO C(7) 
CONT H(81) TO C ( 8) TO C(9) 
PLANAR C ( 8) C(7) C(9) H(81) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 9) to H(91) 
REST 0.074, 0.002 = H(91,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(91) TO C ( 9) TO C(8) 
CONT H(91) TO C ( 9) TO C(10) 
PLANAR C ( 9) C(8) C(10) H(91) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 10) to H(101) 
REST 0.080, 0.002 = H(101,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(101) TO C ( 10) TO C(9) 
CONT H(101) TO C ( 10) TO C(11) 
PLANAR C ( 10) C(9) C(11) H(101) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 11) to H(111) 
REST 0.068, 0.002 = H(111,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(111) TO C ( 11) TO C(10) 
CONT H(111) TO C ( 11) TO C(12) 
PLANAR C ( 11) C(10) C(12) H(111) 
REM            3 H on sp 3
DIST 0.96, 0.02 = 
CONT C ( 18) to H(183) 
CONT C ( 18) to H(182) 
CONT C ( 18) to H(181) 
REST 0.080, 0.002 = H(183,U[ISO]) 
REST 0.080, 0.002 = H(182,U[ISO]) 
REST 0.080, 0.002 = H(181,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(2) to C ( 18) to H(183) 
CONT C(2) to C ( 18) to H(182) 
CONT C(2) to C ( 18) to H(181) 
ANGLE 0.0, 2.0 = mean H(183) to C ( 18) to H(182) 
CONT H(183) to C ( 18) to H(181) 
CONT H(182) to C ( 18) to H(181) 
REM            H1-N-R2
DIST 0.86, 0.02 = 
CONT N ( 6) to H(61) 
REST 0.046, 0.002 = H(61,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(61) TO N ( 6) TO C(5) 
CONT H(61) TO N ( 6) TO C(7) 
PLANAR 0.010000  C(5) C(7) N(6) H(61) 
END
;
_chemical_name_common            ROY
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
