# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_OP_0p108GPa
_database_code_depnum_ccdc_archive 'CCDC 1878576'
_audit_update_record             
;
2018-11-13 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT340_ROY_OP_0p108GPa     
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.02791 Ang.
RESPONSE: Much of the intramolecular geometry was held fixed to known bond distances and angles (CSD: QAXMEH03)- these are not expected to change  significantly over the course of compression. Please see the main manuscript for discussion of intramolecular geometry
;
_vrf_PLAT430_ROY_OP_0p108GPa     
;
PROBLEM: Short Inter D...A Contact O1 ..O1 . 2.85 Ang.
RESPONSE: These are high pressure data - short contacts are to be expected
;

_chemical_name_systematic        
;
5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
;
_chemical_name_common            ROY
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 N3 O2 S1'

_chemical_formula_structural     ?
_chemical_formula_sum            'C12 H9 N3 O2 S1'
_chemical_formula_iupac          ?
_chemical_formula_weight         259.28
_chemical_compound_source        'TCI Chemicals'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   7.9313(8)
_cell_length_b                   13.313(2)
_cell_length_c                   11.6544(17)
_cell_angle_alpha                90
_cell_angle_beta                 104.509(12)
_cell_angle_gamma                90
_cell_volume                     1191.3(3)
_cell_formula_units_Z            4

_cell_measurement_temperature    295
_cell_measurement_pressure       0.108(4) #GPa

_cell_special_details            
;
Cell parameters included in refinement
;

_exptl_crystal_density_diffrn    1.446

_pd_spec_mounting                'TiZr Capsule'
_pd_spec_mount_mode              transmission
_pd_char_colour                  Orange
_chemical_absolute_configuration .

_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
Calculated using MANTID routines.
;

_pd_instr_location               
'ISIS Neutron Facility, Rutherford Appleton Laboratory'
_diffrn_ambient_temperature      295
_diffrn_source                   'Pulsed neutron source'
_diffrn_source_target            W
_diffrn_radiation_type           Neutron
_diffrn_measurement_device_type  'PEARL diffractometer'
_diffrn_radiation_monochromator  none
_diffrn_detector                 'ZnS scintillator'
_diffrn_detector_type            custom

_pd_meas_scan_method             Time-of-flight
_pd_meas_special_details         
;
Time of flight method using a pulsed neutron source
;

# The following three items are used for time-of-flight measurements only.

_pd_instr_dist_src/spec          12800
_pd_instr_dist_spec/detc         800
_pd_meas_2theta_fixed            90

_pd_proc_ls_profile_function     
;
Voigt function convoluted with a back-to-back double exponential.
;

_pd_proc_ls_background_function  'Chebychev polynomial'

_pd_proc_ls_pref_orient_corr     
;
No requirement for preferred orientation correction
;

_pd_proc_ls_prof_R_factor        7.063
_pd_proc_ls_prof_wR_factor       2.345
_pd_proc_ls_prof_R_expected      2.434
_refine_ls_goodness_of_fit_all   0.861
_refine_ls_R_I_factor            1.815

_refine_ls_matrix_type           sparse
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     57
_refine_ls_number_restraints     4
_refine_ls_number_constraints    ?
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_shift/su_max          <0.001

_pd_proc_info_excluded_regions   
;
?

;
_pd_proc_info_data_reduction     
;
Custom ISIS software
;

_refine_special_details          
;The refinement used DFT-optimised structures as a source of restraint on 

torsion angles. A Z-matrix was used, so that distances, angles and 

torsions were refined. Please see the manuscript for a full description 

of refinement details.



Check-cif alerts



PROBLEM: _diffrn_radiation_wavelength is missing

PROBLEM: No Wavelength found in CIF - 0.71073 Ang Assumed     Please Check

RESPONSE: The time of flight method was used





PROBLEM: Short Inter D...A Contact  O1     ..  O1      ..       2.85 Ang

RESPONSE: These are high pressure data - short contacts are to be 

expected.





PROBLEM: _atom_site_U_iso_or_equiv is missing

RESPONSE: Topas outputs atomic displacement parameters expressed as 'B' instead

of 'U'. Isotropic B values are given below.





PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02791 Ang

PROBLEM: Bond    Calc     1.73(2), Rep     1.73000 ......    Missing s.u.  

PROBLEM: Angle   Calc    92.5(11), Rep       92.50 ......    Missing s.u.  

PROBLEM: Torsion Calc       14(5), Rep       14.00 ......    Missing s.u.  

(Numerous)



RESPONSE: Much of the intramolecular geometry was held fixed to known

bond distances and angles (CSD: QAXMEH03)- these are not expected to change 

significantly over the course of compression. Please see the main manuscript

for discussion of intramolecular geometry.,The molecular geometry was refined using a constrained and restrained rigid body, using a Z-matrix formalism. Please see main manuscript for full details.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
N1 N 4 -0.015(3) 0.6719(12) 0.6656(11) 1 0.79(12)
N2 N 4 -0.242(2) 0.5078(10) 0.4225(11) 1 0.79(12)
N3 N 4 0.083(5) 0.565(2) 0.8788(11) 1 0.79(12)
O1 O 4 0.160(7) 0.530(3) 0.9754(13) 1 0.79(12)
O2 O 4 0.069(6) 0.518(2) 0.7861(13) 1 0.79(12)
S1 S 4 0.061(3) 0.8386(10) 0.5469(16) 1 0.79(12)
C1 C 4 -0.040(4) 0.7154(15) 0.7680(14) 1 0.79(12)
C2 C 4 -0.112(6) 0.8104(17) 0.764(2) 1 0.79(12)
C3 C 4 -0.137(8) 0.854(2) 0.866(2) 1 0.79(12)
C4 C 4 -0.090(8) 0.802(2) 0.973(2) 1 0.79(12)
C5 C 4 -0.018(6) 0.707(2) 0.9769(15) 1 0.79(12)
C6 C 4 0.008(5) 0.6639(18) 0.8745(12) 1 0.79(12)
C7 C 4 -0.023(3) 0.7206(10) 0.5593(12) 1 0.79(12)
C8 C 4 -0.098(2) 0.6821(9) 0.4504(11) 1 0.79(12)
C9 C 4 -0.088(3) 0.7483(9) 0.3557(13) 1 0.79(12)
C10 C 4 -0.006(3) 0.8361(9) 0.3940(16) 1 0.79(12)
C11 C 4 0.030(4) 0.9230(10) 0.3230(19) 1 0.79(12)
C12 C 4 -0.179(2) 0.5851(10) 0.4349(10) 1 0.79(12)
H1 H 4 0.017(8) 0.5992(16) 0.6651(18) 1 0.95(15)
H2 H 4 -0.150(6) 0.8513(18) 0.679(2) 1 0.95(15)
H3 H 4 -0.195(10) 0.929(2) 0.863(3) 1 0.95(15)
H4 H 4 -0.110(9) 0.837(3) 1.054(3) 1 0.95(15)
H5 H 4 0.020(7) 0.666(2) 1.0615(14) 1 0.95(15)
H9 H 4 -0.142(3) 0.7302(11) 0.2616(12) 1 0.95(15)
H111 H 4 -0.026(6) 0.9916(11) 0.351(3) 1 0.95(15)
H112 H 4 0.171(4) 0.933(2) 0.337(3) 1 0.95(15)
H113 H 4 -0.029(6) 0.9091(17) 0.2284(19) 1 0.95(15)


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S(1) C(7) 1.73(2) . . no
S(1) C(10) 1.73(3) . . no
O(1) N(3) 1.23(3) . . no
O(2) N(3) 1.23(3) . . no
N(1) C(1) 1.39(2) . . no
N(1) C(7) 1.39(2) . . no
N(2) C(12) 1.14(2) . . no
N(3) C(6) 1.44(4) . . no
C(1) C(2) 1.38(4) . . no
C(1) C(6) 1.39(2) . . no
C(2) C(3) 1.38(4) . . no
C(3) C(4) 1.39(3) . . no
C(4) C(5) 1.38(5) . . no
C(5) C(6) 1.39(3) . . no
C(7) C(8) 1.360(19) . . no
C(8) C(9) 1.430(19) . . no
C(8) C(12) 1.434(19) . . no
C(9) C(10) 1.36(2) . . no
C(10) C(11) 1.49(2) . . no
N(1) H(1) 1.00(3) . . no
C(2) H(2) 1.10(3) . . no
C(3) H(3) 1.10(5) . . no
C(4) H(4) 1.10(5) . . no
C(5) H(5) 1.10(3) . . no
C(9) H(9) 1.10(2) . . no
C(11) H(111) 1.10(3) . . no
C(11) H(112) 1.10(5) . . no
C(11) H(113) 1.10(3) . . no


loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(7) S(1) C(10) 92.5(11) . . . no
C(1) N(1) C(7) 126.2(16) . . . no
O(1) N(3) O(2) 122(3) . . . no
O(1) N(3) C(6) 119(2) . . . no
O(2) N(3) C(6) 119(2) . . . no
N(1) C(1) C(2) 120.0(17) . . . no
N(1) C(1) C(6) 120(2) . . . no
C(2) C(1) C(6) 120(2) . . . no
C(1) C(2) C(3) 120(2) . . . no
C(2) C(3) C(4) 120(3) . . . no
C(3) C(4) C(5) 120(3) . . . no
C(4) C(5) C(6) 120(2) . . . no
N(3) C(6) C(1) 120.1(18) . . . no
N(3) C(6) C(5) 119.9(17) . . . no
C(1) C(6) C(5) 120(2) . . . no
S(1) C(7) N(1) 124.6(13) . . . no
S(1) C(7) C(8) 110.7(12) . . . no
N(1) C(7) C(8) 124.7(15) . . . no
C(7) C(8) C(9) 113.1(12) . . . no
C(7) C(8) C(12) 122.3(12) . . . no
C(9) C(8) C(12) 124.6(12) . . . no
C(8) C(9) C(10) 113.1(14) . . . no
S(1) C(10) C(9) 110.7(13) . . . no
S(1) C(10) C(11) 120.4(14) . . . no
C(9) C(10) C(11) 128.9(17) . . . no
N(2) C(12) C(8) 179.4(19) . . . no
C(1) N(1) H(1) 120(2) . . . no
C(7) N(1) H(1) 114(2) . . . no
C(1) C(2) H(2) 120(3) . . . no
C(3) C(2) H(2) 120(3) . . . no
C(2) C(3) H(3) 120(3) . . . no
C(4) C(3) H(3) 120(4) . . . no
C(3) C(4) H(4) 120(4) . . . no
C(5) C(4) H(4) 120(3) . . . no
C(4) C(5) H(5) 120(3) . . . no
C(6) C(5) H(5) 120(3) . . . no
C(8) C(9) H(9) 123.5(16) . . . no
C(10) C(9) H(9) 123.5(16) . . . no
C(10) C(11) H(111) 109(3) . . . no
C(10) C(11) H(112) 110(2) . . . no
C(10) C(11) H(113) 110(2) . . . no
H(111) C(11) H(112) 109(3) . . . no
H(111) C(11) H(113) 110(3) . . . no
H(112) C(11) H(113) 109(4) . . . no


loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C(10) S(1) C(7) N(1) -180(2) . . . . no
C(10) S(1) C(7) C(8) 0(2) . . . . no
C(7) S(1) C(10) C(9) 0(2) . . . . no
C(7) S(1) C(10) C(11) -180(2) . . . . no
C(7) N(1) C(1) C(2) 14(5) . . . . no
C(7) N(1) C(1) C(6) -166(3) . . . . no
C(1) N(1) C(7) S(1) 41(4) . . . . no
C(1) N(1) C(7) C(8) -139(2) . . . . no
O(1) N(3) C(6) C(1) 164(4) . . . . no
O(1) N(3) C(6) C(5) -17(6) . . . . no
O(2) N(3) C(6) C(1) -16(6) . . . . no
O(2) N(3) C(6) C(5) 163(4) . . . . no
N(1) C(1) C(2) C(3) -180(4) . . . . no
C(6) C(1) C(2) C(3) 0(6) . . . . no
N(1) C(1) C(6) N(3) 0(5) . . . . no
N(1) C(1) C(6) C(5) -180(3) . . . . no
C(2) C(1) C(6) N(3) -180(4) . . . . no
C(2) C(1) C(6) C(5) 1(5) . . . . no
C(1) C(2) C(3) C(4) 0(8) . . . . no
C(2) C(3) C(4) C(5) 0(9) . . . . no
C(3) C(4) C(5) C(6) 0(8) . . . . no
_exptl_crystal_colour            Orange
_exptl_crystal_recrystallization_method 'Used as supplied'
####################################################################### 
# 
# 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_OP_0p237GPa
_database_code_depnum_ccdc_archive 'CCDC 1878579'
_audit_update_record             
;
2018-11-13 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT340_ROY_OP_0p237GPa     
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.02327 Ang.
RESPONSE: Much of the intramolecular geometry was held fixed to known bond distances and angles (CSD: QAXMEH03)- these are not expected to change  significantly over the course of compression. Please see the main manuscript for discussion of intramolecular geometry
;
_vrf_PLAT430_ROY_OP_0p237GPa     
;
PROBLEM: Short Inter D...A Contact O1 ..O1 . 2.88 Ang.
RESPONSE: These are high pressure data - short contacts are to be expected
;

_chemical_name_systematic        
;
5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
;
_chemical_name_common            ROY
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 N3 O2 S1'

_chemical_formula_structural     ?
_chemical_formula_sum            'C12 H9 N3 O2 S1'
_chemical_formula_iupac          ?
_chemical_formula_weight         259.28
_chemical_compound_source        'TCI Chemicals'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   7.7929(5)
_cell_length_b                   13.2989(18)
_cell_length_c                   11.5902(13)
_cell_angle_alpha                90
_cell_angle_beta                 104.082(8)
_cell_angle_gamma                90
_cell_volume                     1165.1(2)
_cell_formula_units_Z            4

_cell_measurement_temperature    295
_cell_measurement_pressure       0.237(5) #GPa

_cell_special_details            
;
Cell parameters included in refinement
;

_exptl_crystal_density_diffrn    1.478

_pd_spec_mounting                'TiZr Capsule'
_pd_spec_mount_mode              transmission
_pd_char_colour                  Orange
_chemical_absolute_configuration .

_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
Calculated using MANTID routines.
;

_pd_instr_location               
'ISIS Neutron Facility, Rutherford Appleton Laboratory'
_diffrn_ambient_temperature      295
_diffrn_source                   'Pulsed neutron source'
_diffrn_source_target            W
_diffrn_radiation_type           Neutron
_diffrn_measurement_device_type  'PEARL diffractometer'
_diffrn_radiation_monochromator  none
_diffrn_detector                 'ZnS scintillator'
_diffrn_detector_type            custom

_pd_meas_scan_method             Time-of-flight
_pd_meas_special_details         
;
Time of flight method using a pulsed neutron source
;

# The following three items are used for time-of-flight measurements only.

_pd_instr_dist_src/spec          12800
_pd_instr_dist_spec/detc         800
_pd_meas_2theta_fixed            90

_pd_proc_ls_profile_function     
;
Voigt function convoluted with a back-to-back double exponential.
;

_pd_proc_ls_background_function  'Chebychev polynomial'

_pd_proc_ls_pref_orient_corr     
;
No requirement for preferred orientation correction
;

_pd_proc_ls_prof_R_factor        2.558
_pd_proc_ls_prof_wR_factor       2.021
_pd_proc_ls_prof_R_expected      2.310
_refine_ls_goodness_of_fit_all   0.875
_refine_ls_R_I_factor            1.299

_refine_ls_matrix_type           sparse
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     49
_refine_ls_number_restraints     4
_refine_ls_number_constraints    ?
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_shift/su_max          <0.001

_pd_proc_info_excluded_regions   
;
?

;
_pd_proc_info_data_reduction     
;
Custom ISIS software
;

_refine_special_details          
;The refinement used DFT-optimised structures as a source of restraint on 

torsion angles. A Z-matrix was used, so that distances, angles and 

torsions were refined. Please see the manuscript for a full description 

of refinement details.



Check-cif alerts



PROBLEM: _diffrn_radiation_wavelength is missing

PROBLEM: No Wavelength found in CIF - 0.71073 Ang Assumed     Please Check

RESPONSE: The time of flight method was used





PROBLEM: Short Inter D...A Contact  O1     ..  O1      ..       2.88 Ang.  

RESPONSE: These are high pressure data - short contacts are to be 

expected.





PROBLEM: _atom_site_U_iso_or_equiv is missing

RESPONSE: Topas outputs atomic displacement parameters expressed as 'B' instead

of 'U'. Isotropic B values are given below.





PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02327 Ang.  

PROBLEM: Bond    Calc   1.726(15), Rep     1.72600 ......    Missing s.u.  

PROBLEM: Angle   Calc     92.5(8), Rep       92.50 ......    Missing s.u.  

PROBLEM: Torsion Calc  -179.8(14), Rep     -180.00 ......    Missing s.u.  

(Numerous)



RESPONSE: Much of the intramolecular geometry was held fixed to known

bond distances and angles (CSD: QAXMEH03)- these are not expected to change 

significantly over the course of compression. Please see the main manuscript

for discussion of intramolecular geometry.,The molecular geometry was refined using a constrained and restrained rigid body, using a Z-matrix formalism. Please see main manuscript for full details.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
N1 N 4 -0.009(2) 0.6725(9) 0.6603(8) 1 1.30(10)
N2 N 4 -0.2348(15) 0.5047(8) 0.4191(8) 1 1.30(10)
N3 N 4 0.083(4) 0.5706(16) 0.8778(8) 1 1.30(10)
O1 O 4 0.161(6) 0.538(2) 0.9759(10) 1 1.30(10)
O2 O 4 0.067(5) 0.5202(15) 0.7869(10) 1 1.30(10)
S1 S 4 0.078(3) 0.8353(8) 0.5382(13) 1 1.30(10)
C1 C 4 -0.036(3) 0.7193(11) 0.7613(11) 1 1.30(10)
C2 C 4 -0.107(5) 0.8151(13) 0.7536(16) 1 1.30(10)
C3 C 4 -0.134(6) 0.8618(16) 0.855(2) 1 1.30(10)
C4 C 4 -0.090(6) 0.8128(17) 0.9632(17) 1 1.30(10)
C5 C 4 -0.018(5) 0.7170(16) 0.9708(12) 1 1.30(10)
C6 C 4 0.009(4) 0.6702(14) 0.8699(9) 1 1.30(10)
C7 C 4 -0.011(2) 0.7185(7) 0.5527(9) 1 1.30(10)
C8 C 4 -0.0845(17) 0.6780(7) 0.4441(8) 1 1.30(10)
C9 C 4 -0.068(2) 0.7417(7) 0.3479(10) 1 1.30(10)
C10 C 4 0.017(2) 0.8296(7) 0.3848(12) 1 1.30(10)
C11 C 4 0.059(3) 0.9142(8) 0.3120(15) 1 1.30(10)
C12 C 4 -0.1681(15) 0.5816(7) 0.4301(8) 1 1.30(10)
H1 H 4 0.022(7) 0.5995(13) 0.6626(14) 1 1.56(12)
H2 H 4 -0.139(5) 0.8502(15) 0.676(2) 1 1.56(12)
H3 H 4 -0.185(8) 0.930(2) 0.849(2) 1 1.56(12)
H4 H 4 -0.109(7) 0.846(2) 1.035(2) 1 1.56(12)
H5 H 4 0.014(5) 0.682(2) 1.0485(17) 1 1.56(12)
H9 H 4 -0.114(2) 0.7237(8) 0.2631(17) 1 1.56(12)
H111 H 4 0.009(5) 0.9774(13) 0.335(3) 1 1.56(12)
H112 H 4 0.189(4) 0.9211(19) 0.326(3) 1 1.56(12)
H113 H 4 0.007(5) 0.9004(15) 0.227(2) 1 1.56(12)


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S(1) C(7) 1.726(18) . . no
S(1) C(10) 1.73(2) . . no
O(1) N(3) 1.23(2) . . no
O(2) N(3) 1.23(2) . . no
N(1) C(1) 1.386(18) . . no
N(1) C(7) 1.386(14) . . no
N(2) C(12) 1.140(15) . . no
N(3) C(6) 1.44(3) . . no
C(1) C(2) 1.38(3) . . no
C(1) C(6) 1.385(18) . . no
C(2) C(3) 1.39(3) . . no
C(3) C(4) 1.38(3) . . no
C(4) C(5) 1.39(4) . . no
C(5) C(6) 1.39(3) . . no
C(7) C(8) 1.361(14) . . no
C(8) C(9) 1.431(15) . . no
C(8) C(12) 1.429(14) . . no
C(9) C(10) 1.360(16) . . no
C(10) C(11) 1.490(19) . . no
N(1) H(1) 1.00(3) . . no
C(2) H(2) 0.99(3) . . no
C(3) H(3) 0.99(4) . . no
C(4) H(4) 0.99(4) . . no
C(5) H(5) 0.99(3) . . no
C(9) H(9) 0.99(2) . . no
C(11) H(111) 0.99(3) . . no
C(11) H(112) 0.99(4) . . no
C(11) H(113) 0.99(3) . . no


loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(7) S(1) C(10) 92.5(8) . . . no
C(1) N(1) C(7) 126.2(11) . . . no
O(1) N(3) O(2) 122(2) . . . no
O(1) N(3) C(6) 118.9(17) . . . no
O(2) N(3) C(6) 119.5(16) . . . no
N(1) C(1) C(2) 120.0(13) . . . no
N(1) C(1) C(6) 119.9(15) . . . no
C(2) C(1) C(6) 120.1(16) . . . no
C(1) C(2) C(3) 119.8(17) . . . no
C(2) C(3) C(4) 120(2) . . . no
C(3) C(4) C(5) 120(2) . . . no
C(4) C(5) C(6) 120.1(16) . . . no
N(3) C(6) C(1) 120.1(14) . . . no
N(3) C(6) C(5) 120.1(13) . . . no
C(1) C(6) C(5) 119.9(19) . . . no
S(1) C(7) N(1) 124.6(10) . . . no
S(1) C(7) C(8) 110.8(9) . . . no
N(1) C(7) C(8) 124.6(10) . . . no
C(7) C(8) C(9) 112.9(9) . . . no
C(7) C(8) C(12) 122.5(9) . . . no
C(9) C(8) C(12) 124.6(9) . . . no
C(8) C(9) C(10) 113.1(10) . . . no
S(1) C(10) C(9) 110.6(10) . . . no
S(1) C(10) C(11) 120.4(11) . . . no
C(9) C(10) C(11) 128.9(12) . . . no
N(2) C(12) C(8) 179.9(16) . . . no
C(1) N(1) H(1) 119.9(16) . . . no
C(7) N(1) H(1) 113.7(17) . . . no
C(1) C(2) H(2) 120(2) . . . no
C(3) C(2) H(2) 120(3) . . . no
C(2) C(3) H(3) 120(3) . . . no
C(4) C(3) H(3) 120(3) . . . no
C(3) C(4) H(4) 120(3) . . . no
C(5) C(4) H(4) 120(2) . . . no
C(4) C(5) H(5) 120(3) . . . no
C(6) C(5) H(5) 120(3) . . . no
C(8) C(9) H(9) 123.4(13) . . . no
C(10) C(9) H(9) 123.4(13) . . . no
C(10) C(11) H(111) 110(3) . . . no
C(10) C(11) H(112) 110(2) . . . no
C(10) C(11) H(113) 109.4(19) . . . no
H(111) C(11) H(112) 109(3) . . . no
H(111) C(11) H(113) 110(3) . . . no
H(112) C(11) H(113) 110(4) . . . no


loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C(10) S(1) C(7) N(1) -179.9(14) . . . . no
C(10) S(1) C(7) C(8) -0.3(16) . . . . no
C(7) S(1) C(10) C(9) 0.1(16) . . . . no
C(7) S(1) C(10) C(11) -179.9(15) . . . . no
C(7) N(1) C(1) C(2) 15(3) . . . . no
C(7) N(1) C(1) C(6) -165(2) . . . . no
C(1) N(1) C(7) S(1) 40(3) . . . . no
C(1) N(1) C(7) C(8) -139.8(18) . . . . no
O(1) N(3) C(6) C(1) 163(3) . . . . no
O(1) N(3) C(6) C(5) -18(5) . . . . no
O(2) N(3) C(6) C(1) -18(5) . . . . no
O(2) N(3) C(6) C(5) 162(3) . . . . no
N(1) C(1) C(2) C(3) 180(3) . . . . no
C(6) C(1) C(2) C(3) 0(5) . . . . no
N(1) C(1) C(6) N(3) 0(4) . . . . no
N(1) C(1) C(6) C(5) 180(3) . . . . no
C(2) C(1) C(6) N(3) -180(3) . . . . no
C(2) C(1) C(6) C(5) 0(4) . . . . no
C(1) C(2) C(3) C(4) 0(6) . . . . no
C(2) C(3) C(4) C(5) 0(6) . . . . no
C(3) C(4) C(5) C(6) 0(6) . . . . no
_exptl_crystal_colour            Orange
_exptl_crystal_recrystallization_method 'Used as supplied'
####################################################################### 
# 
# 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_OP_0p563GPa
_database_code_depnum_ccdc_archive 'CCDC 1878581'
_audit_update_record             
;
2018-11-13 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT340_ROY_OP_0p563GPa     
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.01918 Ang. 
RESPONSE: Much of the intramolecular geometry was held fixed to known bond distances and angles (CSD: QAXMEH03)- these are not expected to change  significantly over the course of compression. Please see the main manuscript for discussion of intramolecular geometry
;
_vrf_PLAT430_ROY_OP_0p563GPa     
;
PROBLEM: Short Inter D...A Contact O2 ..N2 . 2.86 Ang.
RESPONSE: These are high pressure data - short contacts are to be expected
;

_chemical_name_systematic        
;
5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
;
_chemical_name_common            ROY
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 N3 O2 S1'

_chemical_formula_structural     ?
_chemical_formula_sum            'C12 H9 N3 O2 S1'
_chemical_formula_iupac          ?
_chemical_formula_weight         259.28
_chemical_compound_source        'TCI Chemicals'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   7.5920(4)
_cell_length_b                   13.2615(14)
_cell_length_c                   11.4988(12)
_cell_angle_alpha                90
_cell_angle_beta                 103.490(8)
_cell_angle_gamma                90
_cell_volume                     1125.79(18)
_cell_formula_units_Z            4

_cell_measurement_temperature    295
_cell_measurement_pressure       0.563(5) #GPa

_cell_special_details            
;
Cell parameters included in refinement
;

_exptl_crystal_density_diffrn    1.530

_pd_spec_mounting                'TiZr Capsule'
_pd_spec_mount_mode              transmission
_pd_char_colour                  Orange
_chemical_absolute_configuration .

_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
Calculated using MANTID routines.
;

_pd_instr_location               
'ISIS Neutron Facility, Rutherford Appleton Laboratory'
_diffrn_ambient_temperature      295
_diffrn_source                   'Pulsed neutron source'
_diffrn_source_target            W
_diffrn_radiation_type           Neutron
_diffrn_measurement_device_type  'PEARL diffractometer'
_diffrn_radiation_monochromator  none
_diffrn_detector                 'ZnS scintillator'
_diffrn_detector_type            custom

_pd_meas_scan_method             Time-of-flight
_pd_meas_special_details         
;
Time of flight method using a pulsed neutron source
;

# The following three items are used for time-of-flight measurements only.

_pd_instr_dist_src/spec          12800
_pd_instr_dist_spec/detc         800
_pd_meas_2theta_fixed            90

_pd_proc_ls_profile_function     
;
Voigt function convoluted with a back-to-back double exponential.
;

_pd_proc_ls_background_function  'Chebychev polynomial'

_pd_proc_ls_pref_orient_corr     
;
No requirement for preferred orientation correction
;

_pd_proc_ls_prof_R_factor        2.375
_pd_proc_ls_prof_wR_factor       1.925
_pd_proc_ls_prof_R_expected      2.352
_refine_ls_goodness_of_fit_all   0.818
_refine_ls_R_I_factor            1.250

_refine_ls_matrix_type           sparse
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     50
_refine_ls_number_restraints     4
_refine_ls_number_constraints    ?
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_shift/su_max          <0.001

_pd_proc_info_excluded_regions   
;
?

;
_pd_proc_info_data_reduction     
;
Custom ISIS software
;

_refine_special_details          
;The refinement used DFT-optimised structures as a source of restraint on 

torsion angles. A Z-matrix was used, so that distances, angles and 

torsions were refined. Please see the manuscript for a full description 

of refinement details.



Check-cif alerts



PROBLEM: _diffrn_radiation_wavelength is missing

PROBLEM: No Wavelength found in CIF - 0.71073 Ang Assumed     Please Check

RESPONSE: The time of flight method was used





PROBLEM: Short Inter D...A Contact  O2     ..  N2      ..       2.86 Ang.  

PROBLEM: Short Inter X...Y Contact  O2     ..  C12     ..       3.00 Ang.

RESPONSE: These are high pressure data - short contacts are to be 

expected





PROBLEM: _atom_site_U_iso_or_equiv is missing

RESPONSE: Topas outputs atomic displacement parameters expressed as 'B' instead

of 'U'. Isotropic B values are given below.





PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01918 Ang.  

PROBLEM: Bond    Calc   1.728(13), Rep     1.72800 ......    Missing s.u.  

PROBLEM: Angle   Calc     92.5(7), Rep       92.50 ......    Missing s.u.  

PROBLEM: Torsion Calc     0.1(12), Rep        0.00 ......    Missing s.u.  

(Numerous)



RESPONSE: Much of the intramolecular geometry was held fixed to known

bond distances and angles (CSD: QAXMEH03)- these are not expected to change 

significantly over the course of compression. Please see the main manuscript

for discussion of intramolecular geometry.,The molecular geometry was refined using a constrained and restrained rigid body, using a Z-matrix formalism. Please see main manuscript for full details.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
N1 N 4 -0.0095(18) 0.6720(8) 0.6593(7) 1 0.69(8)
N2 N 4 -0.2278(12) 0.5013(6) 0.4165(7) 1 0.69(8)
N3 N 4 0.090(4) 0.5682(14) 0.8766(7) 1 0.69(8)
O1 O 4 0.175(5) 0.536(2) 0.9737(8) 1 0.69(8)
O2 O 4 0.069(4) 0.5176(13) 0.7847(9) 1 0.69(8)
S1 S 4 0.071(2) 0.8382(6) 0.5367(10) 1 0.69(8)
C1 C 4 -0.035(3) 0.7179(10) 0.7623(9) 1 0.69(8)
C2 C 4 -0.108(4) 0.8139(11) 0.7568(14) 1 0.69(8)
C3 C 4 -0.134(5) 0.8598(14) 0.8599(17) 1 0.69(8)
C4 C 4 -0.086(5) 0.8098(14) 0.9684(15) 1 0.69(8)
C5 C 4 -0.012(4) 0.7139(14) 0.9739(10) 1 0.69(8)
C6 C 4 0.013(3) 0.6679(12) 0.8709(8) 1 0.69(8)
C7 C 4 -0.0138(17) 0.7191(6) 0.5512(8) 1 0.69(8)
C8 C 4 -0.0850(14) 0.6780(6) 0.4419(7) 1 0.69(8)
C9 C 4 -0.0715(17) 0.7432(6) 0.3453(8) 1 0.69(8)
C10 C 4 0.010(2) 0.8327(6) 0.3825(10) 1 0.69(8)
C11 C 4 0.048(3) 0.9191(7) 0.3094(13) 1 0.69(8)
C12 C 4 -0.1645(12) 0.5797(6) 0.4278(6) 1 0.69(8)
H1 H 4 0.018(6) 0.605(4) 0.6599(12) 1 0.83(10)
H2 H 4 -0.143(4) 0.8501(13) 0.6783(19) 1 0.83(10)
H3 H 4 -0.187(7) 0.9292(19) 0.856(2) 1 0.83(10)
H4 H 4 -0.104(7) 0.8430(17) 1.043(2) 1 0.83(10)
H5 H 4 0.023(5) 0.6777(17) 1.0524(14) 1 0.83(10)
H9 H 4 -0.1171(19) 0.7248(7) 0.2590(14) 1 0.83(10)
H111 H 4 -0.003(4) 0.9825(11) 0.336(2) 1 0.83(10)
H112 H 4 0.182(3) 0.9265(15) 0.320(2) 1 0.83(10)
H113 H 4 -0.009(4) 0.9065(12) 0.2230(17) 1 0.83(10)


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S(1) C(7) 1.728(13) . . no
S(1) C(10) 1.726(16) . . no
O(1) N(3) 1.23(2) . . no
O(2) N(3) 1.230(18) . . no
N(1) C(1) 1.385(16) . . no
N(1) C(7) 1.385(12) . . no
N(2) C(12) 1.140(12) . . no
N(3) C(6) 1.44(3) . . no
C(1) C(2) 1.38(2) . . no
C(1) C(6) 1.386(15) . . no
C(2) C(3) 1.39(3) . . no
C(3) C(4) 1.39(3) . . no
C(4) C(5) 1.39(3) . . no
C(5) C(6) 1.38(2) . . no
C(7) C(8) 1.361(12) . . no
C(8) C(9) 1.430(12) . . no
C(8) C(12) 1.430(12) . . no
C(9) C(10) 1.361(13) . . no
C(10) C(11) 1.489(17) . . no
N(1) H(1) 0.91(5) . . no
C(2) H(2) 1.00(3) . . no
C(3) H(3) 1.00(4) . . no
C(4) H(4) 1.00(3) . . no
C(5) H(5) 1.00(2) . . no
C(9) H(9) 1.002(18) . . no
C(11) H(111) 1.00(2) . . no
C(11) H(112) 1.00(3) . . no
C(11) H(113) 1.00(2) . . no


loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(7) S(1) C(10) 92.5(7) . . . no
C(1) N(1) C(7) 126.2(10) . . . no
O(1) N(3) O(2) 122(2) . . . no
O(1) N(3) C(6) 118.8(16) . . . no
O(2) N(3) C(6) 119.4(14) . . . no
N(1) C(1) C(2) 120.0(11) . . . no
N(1) C(1) C(6) 120.0(13) . . . no
C(2) C(1) C(6) 120.0(13) . . . no
C(1) C(2) C(3) 120.0(15) . . . no
C(2) C(3) C(4) 120(2) . . . no
C(3) C(4) C(5) 120.0(18) . . . no
C(4) C(5) C(6) 120.0(14) . . . no
N(3) C(6) C(1) 119.9(12) . . . no
N(3) C(6) C(5) 120.0(11) . . . no
C(1) C(6) C(5) 120.0(16) . . . no
S(1) C(7) N(1) 124.6(8) . . . no
S(1) C(7) C(8) 110.7(8) . . . no
N(1) C(7) C(8) 124.7(9) . . . no
C(7) C(8) C(9) 113.0(8) . . . no
C(7) C(8) C(12) 122.4(7) . . . no
C(9) C(8) C(12) 124.6(7) . . . no
C(8) C(9) C(10) 113.1(8) . . . no
S(1) C(10) C(9) 110.7(8) . . . no
S(1) C(10) C(11) 120.4(9) . . . no
C(9) C(10) C(11) 128.9(10) . . . no
N(2) C(12) C(8) 180.0(13) . . . no
C(1) N(1) H(1) 119.9(14) . . . no
C(7) N(1) H(1) 113.8(15) . . . no
C(1) C(2) H(2) 120(2) . . . no
C(3) C(2) H(2) 120(2) . . . no
C(2) C(3) H(3) 120(2) . . . no
C(4) C(3) H(3) 120(3) . . . no
C(3) C(4) H(4) 120(3) . . . no
C(5) C(4) H(4) 120(2) . . . no
C(4) C(5) H(5) 120(2) . . . no
C(6) C(5) H(5) 120(2) . . . no
C(8) C(9) H(9) 123.5(10) . . . no
C(10) C(9) H(9) 123.4(11) . . . no
C(10) C(11) H(111) 110(2) . . . no
C(10) C(11) H(112) 109.4(18) . . . no
C(10) C(11) H(113) 109.6(16) . . . no
H(111) C(11) H(112) 110(2) . . . no
H(111) C(11) H(113) 110(2) . . . no
H(112) C(11) H(113) 109(3) . . . no

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C(10) S(1) C(7) N(1) 180.0(12) . . . . no
C(10) S(1) C(7) C(8) 0.1(12) . . . . no
C(7) S(1) C(10) C(9) 0.0(13) . . . . no
C(7) S(1) C(10) C(11) 179.9(14) . . . . no
C(7) N(1) C(1) C(2) 15(3) . . . . no
C(7) N(1) C(1) C(6) -165.2(17) . . . . no
C(1) N(1) C(7) S(1) 38(2) . . . . no
C(1) N(1) C(7) C(8) -142.3(16) . . . . no
O(1) N(3) C(6) C(1) 161(3) . . . . no
O(1) N(3) C(6) C(5) -19(4) . . . . no
O(2) N(3) C(6) C(1) -19(4) . . . . no
O(2) N(3) C(6) C(5) 161(3) . . . . no
N(1) C(1) C(2) C(3) 180(2) . . . . no
C(6) C(1) C(2) C(3) 0(4) . . . . no
N(1) C(1) C(6) N(3) 0(3) . . . . no
N(1) C(1) C(6) C(5) 180(2) . . . . no
C(2) C(1) C(6) N(3) -180(2) . . . . no
C(2) C(1) C(6) C(5) 0(3) . . . . no
C(1) C(2) C(3) C(4) 0(5) . . . . no
C(2) C(3) C(4) C(5) 0(5) . . . . no
C(3) C(4) C(5) C(6) 0(5) . . . . no
_exptl_crystal_colour            Orange
_exptl_crystal_recrystallization_method 'Used as supplied'
####################################################################### 
# 
# 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_OP_0p767GPa
_database_code_depnum_ccdc_archive 'CCDC 1878582'
_audit_update_record             
;
2018-11-13 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT340_ROY_OP_0p767GPa     
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.01718 Ang. 
RESPONSE: Much of the intramolecular geometry was held fixed to known bond distances and angles (CSD: QAXMEH03)- these are not expected to change  significantly over the course of compression. Please see the main manuscript for discussion of intramolecular geometry
;
_vrf_PLAT430_ROY_OP_0p767GPa     
;
PROBLEM: Short Inter D...A Contact O2 ..N2 . 2.82 Ang.
RESPONSE: These are high pressure data - short contacts are to be expected
;
_vrf_PLAT413_ROY_OP_0p767GPa     
;
PROBLEM: Short Inter XH3 .. XHn H4 ..H113 . 2.07 Ang.
RESPONSE: Wood et al (CrystEngComm, 2008, 10, 368-376) have shown that the lower limit for H...H contacts in high-pressure structures is 1.7 A.
;

_chemical_name_systematic        
;
5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
;
_chemical_name_common            ROY
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 N3 O2 S1'

_chemical_formula_structural     ?
_chemical_formula_sum            'C12 H9 N3 O2 S1'
_chemical_formula_iupac          ?
_chemical_formula_weight         259.28
_chemical_compound_source        'TCI Chemicals'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   7.4909(4)
_cell_length_b                   13.2386(14)
_cell_length_c                   11.4562(11)
_cell_angle_alpha                90
_cell_angle_beta                 103.241(7)
_cell_angle_gamma                90
_cell_volume                     1105.91(17)
_cell_formula_units_Z            4

_cell_measurement_temperature    295
_cell_measurement_pressure       0.767(4) #GPa

_cell_special_details            
;
Cell parameters included in refinement
;

_exptl_crystal_density_diffrn    1.557

_pd_spec_mounting                'TiZr Capsule'
_pd_spec_mount_mode              transmission
_pd_char_colour                  Orange
_chemical_absolute_configuration .

_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
Calculated using MANTID routines.
;

_pd_instr_location               
'ISIS Neutron Facility, Rutherford Appleton Laboratory'
_diffrn_ambient_temperature      295
_diffrn_source                   'Pulsed neutron source'
_diffrn_source_target            W
_diffrn_radiation_type           Neutron
_diffrn_measurement_device_type  'PEARL diffractometer'
_diffrn_radiation_monochromator  none
_diffrn_detector                 'ZnS scintillator'
_diffrn_detector_type            custom

_pd_meas_scan_method             Time-of-flight
_pd_meas_special_details         
;
Time of flight method using a pulsed neutron source
;

# The following three items are used for time-of-flight measurements only.

_pd_instr_dist_src/spec          12800
_pd_instr_dist_spec/detc         800
_pd_meas_2theta_fixed            90

_pd_proc_ls_profile_function     
;
Voigt function convoluted with a back-to-back double exponential.
;

_pd_proc_ls_background_function  'Chebychev polynomial'

_pd_proc_ls_pref_orient_corr     
;
No requirement for preferred orientation correction
;

_pd_proc_ls_prof_R_factor        2.223
_pd_proc_ls_prof_wR_factor       1.816
_pd_proc_ls_prof_R_expected      2.203
_refine_ls_goodness_of_fit_all   0.824
_refine_ls_R_I_factor            1.233

_refine_ls_matrix_type           sparse
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     50
_refine_ls_number_restraints     4
_refine_ls_number_constraints    ?
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_shift/su_max          <0.001

_pd_proc_info_excluded_regions   
;
?

;
_pd_proc_info_data_reduction     
;
Custom ISIS software
;

_refine_special_details          
;The refinement used DFT-optimised structures as a source of restraint on 

torsion angles. A Z-matrix was used, so that distances, angles and 

torsions were refined. Please see the manuscript for a full description 

of refinement details.



Check-cif alerts



PROBLEM: _diffrn_radiation_wavelength is missing

PROBLEM: No Wavelength found in CIF - 0.71073 Ang Assumed     Please Check

RESPONSE: The time of flight method was used





PROBLEM: Short Inter D...A Contact  O2     ..  N2      ..       2.82 Ang.  

PROBLEM: Short Inter X...Y Contact  O2     ..  C12     ..       2.96 Ang. 

PROBLEM: Short Inter XH3 .. XHn     H4     ..  H113    ..       2.07 Ang.  



RESPONSE: These are high pressure data - short contacts are to be 

expected





PROBLEM: _atom_site_U_iso_or_equiv is missing

RESPONSE: Topas outputs atomic displacement parameters expressed as 'B' instead

of 'U'. Isotropic B values are given below.





PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01718 Ang.

PROBLEM: Bond    Calc   1.727(13), Rep     1.72700 ......    Missing s.u.  

PROBLEM: Angle   Calc     92.5(6), Rep       92.50 ......    Missing s.u.  

PROBLEM: Torsion Calc       15(2), Rep       15.00 ......    Missing s.u.  

(Numerous)



RESPONSE: Much of the intramolecular geometry was held fixed to known

bond distances and angles (CSD: QAXMEH03)- these are not expected to change 

significantly over the course of compression. Please see the main manuscript

for discussion of intramolecular geometry.,The molecular geometry was refined using a constrained and restrained rigid body, using a Z-matrix formalism. Please see main manuscript for full details.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
N1 N 4 -0.0104(17) 0.6724(7) 0.6583(6) 1 0.77(8)
N2 N 4 -0.2244(11) 0.4994(6) 0.4156(6) 1 0.77(8)
N3 N 4 0.089(3) 0.5681(12) 0.8760(6) 1 0.77(8)
O1 O 4 0.175(5) 0.5356(18) 0.9731(8) 1 0.77(8)
O2 O 4 0.066(4) 0.5173(11) 0.7839(8) 1 0.77(8)
S1 S 4 0.0673(19) 0.8395(6) 0.5347(9) 1 0.77(8)
C1 C 4 -0.036(2) 0.7185(9) 0.7618(8) 1 0.77(8)
C2 C 4 -0.110(4) 0.8148(10) 0.7565(12) 1 0.77(8)
C3 C 4 -0.135(5) 0.8609(12) 0.8600(15) 1 0.77(8)
C4 C 4 -0.087(5) 0.8106(13) 0.9688(13) 1 0.77(8)
C5 C 4 -0.014(4) 0.7143(13) 0.9740(9) 1 0.77(8)
C6 C 4 0.012(3) 0.6682(11) 0.8705(7) 1 0.77(8)
C7 C 4 -0.0150(15) 0.7195(6) 0.5497(7) 1 0.77(8)
C8 C 4 -0.0851(13) 0.6777(5) 0.4403(6) 1 0.77(8)
C9 C 4 -0.0723(16) 0.7430(5) 0.3431(7) 1 0.77(8)
C10 C 4 0.0071(19) 0.8334(5) 0.3801(9) 1 0.77(8)
C11 C 4 0.044(2) 0.9203(6) 0.3064(11) 1 0.77(8)
C12 C 4 -0.1626(11) 0.5785(6) 0.4265(6) 1 0.77(8)
H1 H 4 0.017(6) 0.602(3) 0.6586(11) 1 0.92(10)
H2 H 4 -0.146(4) 0.8524(12) 0.6751(17) 1 0.92(10)
H3 H 4 -0.190(6) 0.9330(17) 0.8561(19) 1 0.92(10)
H4 H 4 -0.106(6) 0.8451(15) 1.0462(18) 1 0.92(10)
H5 H 4 0.022(5) 0.6767(15) 1.0554(13) 1 0.92(10)
H9 H 4 -0.1188(17) 0.7235(7) 0.2536(13) 1 0.92(10)
H111 H 4 -0.020(4) 0.9844(10) 0.329(2) 1 0.92(10)
H112 H 4 0.184(3) 0.9330(14) 0.323(2) 1 0.92(10)
H113 H 4 -0.006(4) 0.9042(10) 0.2162(16) 1 0.92(10)


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S(1) C(7) 1.727(13) S(1) C(10) 1.727(14)
O(1) N(3) 1.23(2) O(2) N(3) 1.230(15)
N(1) C(1) 1.385(13) N(1) C(7) 1.385(11)
N(2) C(12) 1.140(11) N(3) C(6) 1.44(2)
C(1) C(2) 1.39(2) C(1) C(6) 1.385(14)
C(2) C(3) 1.38(3) C(3) C(4) 1.39(2)
C(4) C(5) 1.38(3) C(5) C(6) 1.386(19)
C(7) C(8) 1.361(10) C(8) C(9) 1.430(10)
C(8) C(12) 1.430(11) C(9) C(10) 1.360(11)
C(10) C(11) 1.490(14) N(1) H(1) 0.95(4)
C(2) H(2) 1.04(2) C(3) H(3) 1.04(3)
C(4) H(4) 1.04(3) C(5) H(5) 1.04(2)
C(9) H(9) 1.037(16) C(11) H(111) 1.04(2)
C(11) H(112) 1.04(3) C(11) H(113) 1.04(2)


loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(7) S(1) C(10) 92.5(6) . . . no
C(1) N(1) C(7) 126.2(9) . . . no
O(1) N(3) O(2) 121.8(19) . . . no
O(1) N(3) C(6) 118.9(14) . . . no
O(2) N(3) C(6) 119.3(12) . . . no
N(1) C(1) C(2) 120.0(10) . . . no
N(1) C(1) C(6) 120.0(11) . . . no
C(2) C(1) C(6) 120.0(11) . . . no
C(1) C(2) C(3) 120.0(13) . . . no
C(2) C(3) C(4) 120.0(18) . . . no
C(3) C(4) C(5) 120.0(17) . . . no
C(4) C(5) C(6) 120.0(12) . . . no
N(3) C(6) C(1) 120.0(10) . . . no
N(3) C(6) C(5) 120.1(10) . . . no
C(1) C(6) C(5) 119.9(14) . . . no
S(1) C(7) N(1) 124.6(7) . . . no
S(1) C(7) C(8) 110.7(7) . . . no
N(1) C(7) C(8) 124.7(8) . . . no
C(7) C(8) C(9) 113.0(7) . . . no
C(7) C(8) C(12) 122.5(7) . . . no
C(9) C(8) C(12) 124.5(6) . . . no
C(8) C(9) C(10) 113.1(7) . . . no
S(1) C(10) C(9) 110.7(7) . . . no
S(1) C(10) C(11) 120.4(8) . . . no
C(9) C(10) C(11) 128.9(9) . . . no
N(2) C(12) C(8) 179.9(12) . . . no
C(1) N(1) H(1) 119.9(13) . . . no
C(7) N(1) H(1) 113.8(13) . . . no
C(1) C(2) H(2) 120.0(18) . . . no
C(3) C(2) H(2) 120(2) . . . no
C(2) C(3) H(3) 120(2) . . . no
C(4) C(3) H(3) 120(2) . . . no
C(3) C(4) H(4) 120(2) . . . no
C(5) C(4) H(4) 120.0(19) . . . no
C(4) C(5) H(5) 120(2) . . . no
C(6) C(5) H(5) 120(2) . . . no
C(8) C(9) H(9) 123.5(9) . . . no
C(10) C(9) H(9) 123.4(10) . . . no
C(10) C(11) H(111) 109.5(17) . . . no
C(10) C(11) H(112) 109.4(15) . . . no
C(10) C(11) H(113) 109.5(13) . . . no
H(111) C(11) H(112) 109(2) . . . no
H(111) C(11) H(113) 110(2) . . . no
H(112) C(11) H(113) 110(2) . . . no


loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C(10) S(1) C(7) N(1) -180.0(11) . . . . no
C(10) S(1) C(7) C(8) 0.0(11) . . . . no
C(7) S(1) C(10) C(9) 0.0(12) . . . . no
C(7) S(1) C(10) C(11) 180.0(11) . . . . no
C(7) N(1) C(1) C(2) 15(2) . . . . no
C(7) N(1) C(1) C(6) -165.6(15) . . . . no
C(1) N(1) C(7) S(1) 36.7(19) . . . . no
C(1) N(1) C(7) C(8) -143.2(13) . . . . no
O(1) N(3) C(6) C(1) 161(3) . . . . no
O(1) N(3) C(6) C(5) -19(4) . . . . no
O(2) N(3) C(6) C(1) -20(3) . . . . no
O(2) N(3) C(6) C(5) 160(3) . . . . no
N(1) C(1) C(2) C(3) -180(2) . . . . no
C(6) C(1) C(2) C(3) 0(4) . . . . no
N(1) C(1) C(6) N(3) 0(3) . . . . no
N(1) C(1) C(6) C(5) -179.9(19) . . . . no
C(2) C(1) C(6) N(3) -180(2) . . . . no
C(2) C(1) C(6) C(5) 0(3) . . . . no
C(1) C(2) C(3) C(4) 0(5) . . . . no
C(2) C(3) C(4) C(5) 0(5) . . . . no
C(3) C(4) C(5) C(6) 0(5) . . . . no
_exptl_crystal_colour            Orange
_exptl_crystal_recrystallization_method 'Used as supplied'
####################################################################### 
# 
# 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_OP_0p171GPa
_database_code_depnum_ccdc_archive 'CCDC 1878578'
_audit_update_record             
;
2018-11-13 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT340_ROY_OP_0p171GPa     
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.02318 Ang.
RESPONSE: Much of the intramolecular geometry was held fixed to known bond distances and angles (CSD: QAXMEH03)- these are not expected to change  significantly over the course of compression. Please see the main manuscript for discussion of intramolecular geometry
;
_vrf_PLAT350_ROY_OP_0p171GPa     
;
PROBLEM: Short C-H (X0.96,N1.08A) C2 - H2 . 0.91 Ang.
RESPONSE: No action taken. A single parameter for C-H bonds was allowed to refine - a search of C-H bonds in the CSD shows this is not abnormally short
;
_vrf_PLAT350_ROY_OP_0p171GPa_2   
;
PROBLEM: Short C-H (X0.96,N1.08A) C3 - H3 . 0.92 Ang.
RESPONSE: No action taken. A single parameter for C-H bonds was allowed to refine - a search of C-H bonds in the CSD shows this is not abnormally short
;
_vrf_PLAT350_ROY_OP_0p171GPa_3   
;
PROBLEM: Short C-H (X0.96,N1.08A) C4 - H4 . 0.91 Ang. 
RESPONSE: No action taken. A single parameter for C-H bonds was allowed to refine - a search of C-H bonds in the CSD shows this is not abnormally short
;
_vrf_PLAT350_ROY_OP_0p171GPa_4   
;
PROBLEM: Short C-H (X0.96,N1.08A) C5 - H5 . 0.91 Ang. 
RESPONSE: No action taken. A single parameter for C-H bonds was allowed to refine - a search of C-H bonds in the CSD shows this is not abnormally short
;
_vrf_PLAT350_ROY_OP_0p171GPa_5   
;
PROBLEM: Short C-H (X0.96,N1.08A) C9 - H9 . 0.91 Ang.
RESPONSE: No action taken. A single parameter for C-H bonds was allowed to refine - a search of C-H bonds in the CSD shows this is not abnormally short
;
_vrf_PLAT350_ROY_OP_0p171GPa_6   
;
PROBLEM: Short C-H (X0.96,N1.08A) C11 - H111 . 0.91 Ang. 
RESPONSE: No action taken. A single parameter for C-H bonds was allowed to refine - a search of C-H bonds in the CSD shows this is not abnormally short
;
_vrf_PLAT350_ROY_OP_0p171GPa_7   
;
PROBLEM: Short C-H (X0.96,N1.08A) C11 - H112 . 0.91 Ang. 
RESPONSE: No action taken. A single parameter for C-H bonds was allowed to refine - a search of C-H bonds in the CSD shows this is not abnormally short
;
_vrf_PLAT350_ROY_OP_0p171GPa_8   
;
PROBLEM: Short C-H (X0.96,N1.08A) C11 - H112 . 0.91 Ang. 
RESPONSE: No action taken. A single parameter for C-H bonds was allowed to refine - a search of C-H bonds in the CSD shows this is not abnormally short
;

_chemical_name_systematic        
;
5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
;
_chemical_name_common            ROY
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 N3 O2 S1'

_chemical_formula_structural     ?
_chemical_formula_sum            'C12 H9 N3 O2 S1'
_chemical_formula_iupac          ?
_chemical_formula_weight         259.28
_chemical_compound_source        'TCI Chemicals'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   7.8517(5)
_cell_length_b                   13.3034(17)
_cell_length_c                   11.6174(11)
_cell_angle_alpha                90
_cell_angle_beta                 104.251(8)
_cell_angle_gamma                90
_cell_volume                     1176.1(2)
_cell_formula_units_Z            4

_cell_measurement_temperature    295
_cell_measurement_pressure       0.171(5) #GPa

_cell_special_details            
;
Cell parameters included in refinement
;

_exptl_crystal_density_diffrn    1.464

_pd_spec_mounting                'TiZr Capsule'
_pd_spec_mount_mode              transmission
_pd_char_colour                  Orange
_chemical_absolute_configuration .

_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
Calculated using MANTID routines.
;

_pd_instr_location               
'ISIS Neutron Facility, Rutherford Appleton Laboratory'
_diffrn_ambient_temperature      295
_diffrn_source                   'Pulsed neutron source'
_diffrn_source_target            W
_diffrn_radiation_type           Neutron
_diffrn_measurement_device_type  'PEARL diffractometer'
_diffrn_radiation_monochromator  none
_diffrn_detector                 'ZnS scintillator'
_diffrn_detector_type            custom

_pd_meas_scan_method             Time-of-flight
_pd_meas_special_details         
;
Time of flight method using a pulsed neutron source
;

# The following three items are used for time-of-flight measurements only.

_pd_instr_dist_src/spec          12800
_pd_instr_dist_spec/detc         800
_pd_meas_2theta_fixed            90

_pd_proc_ls_profile_function     
;
Voigt function convoluted with a back-to-back double exponential.
;

_pd_proc_ls_background_function  'Chebychev polynomial'

_pd_proc_ls_pref_orient_corr     
;
No requirement for preferred orientation correction
;

_pd_proc_ls_prof_R_factor        2.415
_pd_proc_ls_prof_wR_factor       1.957
_pd_proc_ls_prof_R_expected      2.297
_refine_ls_goodness_of_fit_all   0.852
_refine_ls_R_I_factor            1.454

_refine_ls_matrix_type           sparse
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     52
_refine_ls_number_restraints     4
_refine_ls_number_constraints    ?
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_shift/su_max          <0.001

_pd_proc_info_excluded_regions   
;
?

;
_pd_proc_info_data_reduction     
;
Custom ISIS software
;

_refine_special_details          
;The refinement used DFT-optimised structures as a source of restraint on 

torsion angles. A Z-matrix was used, so that distances, angles and 

torsions were refined. Please see the manuscript for a full description 

of refinement details.



Check-cif alerts



PROBLEM: _diffrn_radiation_wavelength is missing

PROBLEM: No Wavelength found in CIF - 0.71073 Ang Assumed     Please Check

RESPONSE: The time of flight method was used





PROBLEM: _atom_site_U_iso_or_equiv is missing

RESPONSE: Topas outputs atomic displacement parameters expressed as 'B' instead

of 'U'. Isotropic B values are given below.





PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02318 Ang. 

PROBLEM: Bond    Calc   1.726(15), Rep     1.72600 ......    Missing s.u.  

PROBLEM: Angle   Calc     92.5(8), Rep       92.50 ......    Missing s.u.  

PROBLEM: Torsion Calc  -179.8(14), Rep     -180.00 ......    Missing s.u.  

(Numerous)



RESPONSE: Much of the intramolecular geometry was held fixed to known

bond distances and angles (CSD: QAXMEH03)- these are not expected to change 

significantly over the course of compression. Please see the main manuscript

for discussion of intramolecular geometry.,The molecular geometry was refined using a constrained and restrained rigid body, using a Z-matrix formalism. Please see main manuscript for full details.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
N1 N 4 -0.011(2) 0.6727(9) 0.6617(8) 1 1.09(9)
N2 N 4 -0.2359(15) 0.5057(8) 0.4199(8) 1 1.09(9)
N3 N 4 0.084(4) 0.5704(16) 0.8786(8) 1 1.09(9)
O1 O 4 0.162(5) 0.538(2) 0.9766(9) 1 1.09(9)
O2 O 4 0.070(5) 0.5206(14) 0.7876(10) 1 1.09(9)
S1 S 4 0.074(2) 0.8363(7) 0.5407(12) 1 1.09(9)
C1 C 4 -0.039(3) 0.7184(11) 0.7624(10) 1 1.09(9)
C2 C 4 -0.113(5) 0.8135(13) 0.7549(15) 1 1.09(9)
C3 C 4 -0.141(6) 0.8592(16) 0.8556(19) 1 1.09(9)
C4 C 4 -0.096(6) 0.8100(17) 0.9639(17) 1 1.09(9)
C5 C 4 -0.022(5) 0.7150(16) 0.9715(12) 1 1.09(9)
C6 C 4 0.007(3) 0.6692(14) 0.8707(9) 1 1.09(9)
C7 C 4 -0.014(2) 0.7193(7) 0.5545(9) 1 1.09(9)
C8 C 4 -0.0875(17) 0.6792(7) 0.4458(8) 1 1.09(9)
C9 C 4 -0.073(2) 0.7435(7) 0.3501(10) 1 1.09(9)
C10 C 4 0.012(2) 0.8313(7) 0.3875(12) 1 1.09(9)
C11 C 4 0.052(3) 0.9165(8) 0.3152(15) 1 1.09(9)
C12 C 4 -0.1701(15) 0.5827(7) 0.4314(7) 1 1.09(9)
H1 H 4 0.020(6) 0.606(4) 0.6636(14) 1 1.31(11)
H2 H 4 -0.143(5) 0.8458(14) 0.684(2) 1 1.31(11)
H3 H 4 -0.190(7) 0.922(2) 0.851(2) 1 1.31(11)
H4 H 4 -0.114(7) 0.8401(19) 1.030(2) 1 1.31(11)
H5 H 4 0.009(5) 0.6826(19) 1.0427(16) 1 1.31(11)
H9 H 4 -0.115(2) 0.7273(8) 0.2722(16) 1 1.31(11)
H111 H 4 0.015(5) 0.9751(12) 0.341(2) 1 1.31(11)
H112 H 4 0.170(4) 0.9197(17) 0.323(3) 1 1.31(11)
H113 H 4 -0.004(5) 0.9068(14) 0.237(2) 1 1.31(11)


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S(1) C(7) 1.726(15) . . no
S(1) C(10) 1.727(19) . . no
O(1) N(3) 1.23(2) . . no
O(2) N(3) 1.23(2) . . no
N(1) C(1) 1.383(18) . . no
N(1) C(7) 1.386(14) . . no
N(2) C(12) 1.140(15) . . no
N(3) C(6) 1.44(3) . . no
C(1) C(2) 1.39(3) . . no
C(1) C(6) 1.385(17) . . no
C(2) C(3) 1.38(3) . . no
C(3) C(4) 1.39(3) . . no
C(4) C(5) 1.39(4) . . no
C(5) C(6) 1.39(3) . . no
C(7) C(8) 1.361(14) . . no
C(8) C(9) 1.429(15) . . no
C(8) C(12) 1.429(14) . . no
C(9) C(10) 1.362(16) . . no
C(10) C(11) 1.490(19) . . no
N(1) H(1) 0.92(5) . . no
C(2) H(2) 0.91(3) . . no
C(3) H(3) 0.92(4) . . no
C(4) H(4) 0.91(4) . . no
C(5) H(5) 0.91(3) . . no
C(9) H(9) 0.91(2) . . no
C(11) H(111) 0.91(3) . . no
C(11) H(112) 0.91(4) . . no
C(11) H(113) 0.92(3) . . no


loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(7) S(1) C(10) 92.5(8) . . . no
C(1) N(1) C(7) 126.3(11) . . . no
O(1) N(3) O(2) 122(2) . . . no
O(1) N(3) C(6) 119.0(17) . . . no
O(2) N(3) C(6) 119.3(16) . . . no
N(1) C(1) C(2) 120.0(12) . . . no
N(1) C(1) C(6) 120.0(15) . . . no
C(2) C(1) C(6) 120.0(15) . . . no
C(1) C(2) C(3) 120.0(17) . . . no
C(2) C(3) C(4) 120(2) . . . no
C(3) C(4) C(5) 120(2) . . . no
C(4) C(5) C(6) 120.0(16) . . . no
N(3) C(6) C(1) 120.1(13) . . . no
N(3) C(6) C(5) 120.0(13) . . . no
C(1) C(6) C(5) 119.9(18) . . . no
S(1) C(7) N(1) 124.6(10) . . . no
S(1) C(7) C(8) 110.8(9) . . . no
N(1) C(7) C(8) 124.6(10) . . . no
C(7) C(8) C(9) 113.0(9) . . . no
C(7) C(8) C(12) 122.5(9) . . . no
C(9) C(8) C(12) 124.6(9) . . . no
C(8) C(9) C(10) 113.1(10) . . . no
S(1) C(10) C(9) 110.7(10) . . . no
S(1) C(10) C(11) 120.5(10) . . . no
C(9) C(10) C(11) 128.9(13) . . . no
N(2) C(12) C(8) 180.0(16) . . . no
C(1) N(1) H(1) 120.0(16) . . . no
C(7) N(1) H(1) 113.5(17) . . . no
C(1) C(2) H(2) 120(3) . . . no
C(3) C(2) H(2) 120(3) . . . no
C(2) C(3) H(3) 120(3) . . . no
C(4) C(3) H(3) 120(3) . . . no
C(3) C(4) H(4) 120(3) . . . no
C(5) C(4) H(4) 120(3) . . . no
C(4) C(5) H(5) 120(3) . . . no
C(6) C(5) H(5) 120(3) . . . no
C(8) C(9) H(9) 123.6(13) . . . no
C(10) C(9) H(9) 123.4(14) . . . no
C(10) C(11) H(111) 110(2) . . . no
C(10) C(11) H(112) 109(2) . . . no
C(10) C(11) H(113) 110(2) . . . no
H(111) C(11) H(112) 109(3) . . . no
H(111) C(11) H(113) 110(3) . . . no
H(112) C(11) H(113) 110(4) . . . no


loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C(10) S(1) C(7) N(1) -179.8(14) . . . . no
C(10) S(1) C(7) C(8) -0.1(14) . . . . no
C(7) S(1) C(10) C(9) 0.3(14) . . . . no
C(7) S(1) C(10) C(11) 179.8(15) . . . . no
C(7) N(1) C(1) C(2) 15(3) . . . . no
C(7) N(1) C(1) C(6) -165.1(19) . . . . no
C(1) N(1) C(7) S(1) 41(3) . . . . no
C(1) N(1) C(7) C(8) -139.1(18) . . . . no
O(1) N(3) C(6) C(1) 163(3) . . . . no
O(1) N(3) C(6) C(5) -18(4) . . . . no
O(2) N(3) C(6) C(1) -18(4) . . . . no
O(2) N(3) C(6) C(5) 162(3) . . . . no
N(1) C(1) C(2) C(3) 180(3) . . . . no
C(6) C(1) C(2) C(3) 0(5) . . . . no
N(1) C(1) C(6) N(3) 0(3) . . . . no
N(1) C(1) C(6) C(5) -180(2) . . . . no
C(2) C(1) C(6) N(3) -180(3) . . . . no
C(2) C(1) C(6) C(5) 0(4) . . . . no
C(1) C(2) C(3) C(4) 0(6) . . . . no
C(2) C(3) C(4) C(5) 0(6) . . . . no
C(3) C(4) C(5) C(6) 0(6) . . . . no
_exptl_crystal_colour            Orange
_exptl_crystal_recrystallization_method 'Used as supplied'
####################################################################### 
# 
# 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_OP_0p382GPa
_database_code_depnum_ccdc_archive 'CCDC 1878580'
_audit_update_record             
;
2018-11-13 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT340_ROY_OP_0p382GPa     
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.01945 Ang.
RESPONSE: Much of the intramolecular geometry was held fixed to known bond distances and angles (CSD: QAXMEH03)- these are not expected to change  significantly over the course of compression. Please see the main manuscript for discussion of intramolecular geometry
;
_vrf_PLAT430_ROY_OP_0p382GPa     
;
PROBLEM: Short Inter D...A Contact O2 ..N2 . 2.86 Ang.
RESPONSE: These are high pressure data - short contacts are to be expected
;

_chemical_name_systematic        
;
5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
;
_chemical_name_common            ROY
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 N3 O2 S1'

_chemical_formula_structural     ?
_chemical_formula_sum            'C12 H9 N3 O2 S1'
_chemical_formula_iupac          ?
_chemical_formula_weight         259.28
_chemical_compound_source        'TCI Chemicals'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   7.6938(5)
_cell_length_b                   13.2818(16)
_cell_length_c                   11.5506(12)
_cell_angle_alpha                90
_cell_angle_beta                 103.783(6)
_cell_angle_gamma                90
_cell_volume                     1146.3(2)
_cell_formula_units_Z            4

_cell_measurement_temperature    295
_cell_measurement_pressure       0.382(4) #GPa

_cell_special_details            
;
Cell parameters included in refinement
;

_exptl_crystal_density_diffrn    1.502

_pd_spec_mounting                'TiZr Capsule'
_pd_spec_mount_mode              transmission
_pd_char_colour                  Orange
_chemical_absolute_configuration .

_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
Calculated using MANTID routines.
;

_pd_instr_location               
'ISIS Neutron Facility, Rutherford Appleton Laboratory'
_diffrn_ambient_temperature      295
_diffrn_source                   'Pulsed neutron source'
_diffrn_source_target            W
_diffrn_radiation_type           Neutron
_diffrn_measurement_device_type  'PEARL diffractometer'
_diffrn_radiation_monochromator  none
_diffrn_detector                 'ZnS scintillator'
_diffrn_detector_type            custom

_pd_meas_scan_method             Time-of-flight
_pd_meas_special_details         
;
Time of flight method using a pulsed neutron source
;

# The following three items are used for time-of-flight measurements only.

_pd_instr_dist_src/spec          12800
_pd_instr_dist_spec/detc         800
_pd_meas_2theta_fixed            90

_pd_proc_ls_profile_function     
;
Voigt function convoluted with a back-to-back double exponential.
;

_pd_proc_ls_background_function  'Chebychev polynomial'

_pd_proc_ls_pref_orient_corr     
;
No requirement for preferred orientation correction
;

_pd_proc_ls_prof_R_factor        2.388
_pd_proc_ls_prof_wR_factor       1.897
_pd_proc_ls_prof_R_expected      2.330
_refine_ls_goodness_of_fit_all   0.814
_refine_ls_R_I_factor            1.198

_refine_ls_matrix_type           sparse
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     50
_refine_ls_number_restraints     4
_refine_ls_number_constraints    ?
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_shift/su_max          <0.001

_pd_proc_info_excluded_regions   
;
?

;
_pd_proc_info_data_reduction     
;
Custom ISIS software
;

_refine_special_details          
;The refinement used DFT-optimised structures as a source of restraint on 

torsion angles. A Z-matrix was used, so that distances, angles and 

torsions were refined. Please see the manuscript for a full description 

of refinement details.



Check-cif alerts



PROBELM: _diffrn_radiation_wavelength is missing

PROBLEM: No Wavelength found in CIF - 0.71073 Ang Assumed     Please Check

RESPONSE: The time of flight method was used





PROBLEM: Short Inter D...A Contact  O2     ..  N2      ..       2.86 Ang. 

PROBLEM: Short Inter X...Y Contact  O2     ..  C12     ..       3.01 Ang.  

RESPONSE: These are high pressure data - short contacts are to be 

expected





PROBLEM: _atom_site_U_iso_or_equiv is missing

RESPONSE: Topas outputs atomic displacement parameters expressed as 'B' instead

of 'U'. Isotropic B values are given below.





PROBELM: Low Bond Precision on  C-C Bonds ...............    0.01945 Ang.

PROBLEM: Bond    Calc   1.725(15), Rep     1.72500 ......    Missing s.u.  

PROBLEM: Angle   Calc     92.6(7), Rep       92.60 ......    Missing s.u.  

PROBLEM: Torsion Calc    -0.1(12), Rep        0.00 ......    Missing s.u.  

(Numerous)



RESPONSE: Much of the intramolecular geometry was held fixed to known

bond distances and angles (CSD: QAXMEH03)- these are not expected to change 

significantly over the course of compression. Please see the main manuscript

for discussion of intramolecular geometry.,The molecular geometry was refined using a constrained and restrained rigid body, using a Z-matrix formalism. Please see main manuscript for full details.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
N1 N 4 -0.0074(19) 0.6726(8) 0.6583(7) 1 0.70(9)
N2 N 4 -0.2292(13) 0.5042(7) 0.4154(7) 1 0.70(9)
N3 N 4 0.090(4) 0.5690(14) 0.8750(7) 1 0.70(9)
O1 O 4 0.172(5) 0.537(2) 0.9724(9) 1 0.70(9)
O2 O 4 0.071(4) 0.5188(13) 0.7834(9) 1 0.70(9)
S1 S 4 0.075(2) 0.8379(7) 0.5371(11) 1 0.70(9)
C1 C 4 -0.034(3) 0.7182(10) 0.7605(9) 1 0.70(9)
C2 C 4 -0.108(4) 0.8138(12) 0.7545(14) 1 0.70(9)
C3 C 4 -0.134(5) 0.8594(14) 0.8567(17) 1 0.70(9)
C4 C 4 -0.087(5) 0.8095(15) 0.9649(15) 1 0.70(9)
C5 C 4 -0.014(4) 0.7139(15) 0.9710(10) 1 0.70(9)
C6 C 4 0.013(3) 0.6683(12) 0.8688(8) 1 0.70(9)
C7 C 4 -0.0111(17) 0.7198(7) 0.5508(8) 1 0.70(9)
C8 C 4 -0.0833(15) 0.6794(6) 0.4416(7) 1 0.70(9)
C9 C 4 -0.0689(17) 0.7444(6) 0.3457(9) 1 0.70(9)
C10 C 4 0.014(2) 0.8331(6) 0.3833(11) 1 0.70(9)
C11 C 4 0.054(3) 0.9191(7) 0.3109(13) 1 0.70(9)
C12 C 4 -0.1645(13) 0.5819(6) 0.4270(7) 1 0.70(9)
H1 H 4 0.023(6) 0.605(4) 0.6594(12) 1 0.84(10)
H2 H 4 -0.141(4) 0.8487(13) 0.6788(19) 1 0.84(10)
H3 H 4 -0.186(7) 0.9262(19) 0.852(2) 1 0.84(10)
H4 H 4 -0.106(6) 0.8414(18) 1.036(2) 1 0.84(10)
H5 H 4 0.019(5) 0.6790(17) 1.0466(15) 1 0.84(10)
H9 H 4 -0.1135(19) 0.7271(8) 0.2624(15) 1 0.84(10)
H111 H 4 -0.001(5) 0.9798(12) 0.333(2) 1 0.84(10)
H112 H 4 0.182(3) 0.9284(17) 0.326(2) 1 0.84(10)
H113 H 4 0.006(5) 0.9052(13) 0.2271(18) 1 0.84(10)


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S(1) C(7) 1.725(15) . . no
S(1) C(10) 1.727(17) . . no
O(1) N(3) 1.23(2) . . no
O(2) N(3) 1.230(18) . . no
N(1) C(1) 1.385(16) . . no
N(1) C(7) 1.385(13) . . no
N(2) C(12) 1.140(13) . . no
N(3) C(6) 1.44(3) . . no
C(1) C(2) 1.39(2) . . no
C(1) C(6) 1.385(16) . . no
C(2) C(3) 1.38(3) . . no
C(3) C(4) 1.38(3) . . no
C(4) C(5) 1.38(3) . . no
C(5) C(6) 1.39(2) . . no
C(7) C(8) 1.362(12) . . no
C(8) C(9) 1.429(13) . . no
C(8) C(12) 1.430(12) . . no
C(9) C(10) 1.361(14) . . no
C(10) C(11) 1.490(17) . . no
N(1) H(1) 0.93(5) . . no
C(2) H(2) 0.97(3) . . no
C(3) H(3) 0.97(4) . . no
C(4) H(4) 0.97(3) . . no
C(5) H(5) 0.97(2) . . no
C(9) H(9) 0.969(19) . . no
C(11) H(111) 0.97(3) . . no
C(11) H(112) 0.97(3) . . no
C(11) H(113) 0.97(3) . . no


loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(7) S(1) C(10) 92.6(7) . . . no
C(1) N(1) C(7) 126.2(10) . . . no
O(1) N(3) O(2) 122(2) . . . no
O(1) N(3) C(6) 118.6(16) . . . no
O(2) N(3) C(6) 119.4(14) . . . no
N(1) C(1) C(2) 120.0(11) . . . no
N(1) C(1) C(6) 120.1(13) . . . no
C(2) C(1) C(6) 119.9(13) . . . no
C(1) C(2) C(3) 120.0(15) . . . no
C(2) C(3) C(4) 120(2) . . . no
C(3) C(4) C(5) 120.1(19) . . . no
C(4) C(5) C(6) 120.0(14) . . . no
N(3) C(6) C(1) 119.9(12) . . . no
N(3) C(6) C(5) 120.1(12) . . . no
C(1) C(6) C(5) 120.0(16) . . . no
S(1) C(7) N(1) 124.6(9) . . . no
S(1) C(7) C(8) 110.8(8) . . . no
N(1) C(7) C(8) 124.7(9) . . . no
C(7) C(8) C(9) 113.0(8) . . . no
C(7) C(8) C(12) 122.4(8) . . . no
C(9) C(8) C(12) 124.6(8) . . . no
C(8) C(9) C(10) 113.1(9) . . . no
S(1) C(10) C(9) 110.6(9) . . . no
S(1) C(10) C(11) 120.5(9) . . . no
C(9) C(10) C(11) 128.9(11) . . . no
N(2) C(12) C(8) 180.0(14) . . . no
C(1) N(1) H(1) 120.0(14) . . . no
C(7) N(1) H(1) 113.7(15) . . . no
C(1) C(2) H(2) 120(2) . . . no
C(3) C(2) H(2) 120(2) . . . no
C(2) C(3) H(3) 120(2) . . . no
C(4) C(3) H(3) 120(3) . . . no
C(3) C(4) H(4) 120(3) . . . no
C(5) C(4) H(4) 120(2) . . . no
C(4) C(5) H(5) 120(2) . . . no
C(6) C(5) H(5) 120(3) . . . no
C(8) C(9) H(9) 123.5(11) . . . no
C(10) C(9) H(9) 123.4(12) . . . no
C(10) C(11) H(111) 109(2) . . . no
C(10) C(11) H(112) 109.5(19) . . . no
C(10) C(11) H(113) 109.5(18) . . . no
H(111) C(11) H(112) 110(3) . . . no
H(111) C(11) H(113) 110(3) . . . no
H(112) C(11) H(113) 110(3) . . . no


loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C(10) S(1) C(7) N(1) 180.0(13) . . . . no
C(10) S(1) C(7) C(8) -0.1(12) . . . . no
C(7) S(1) C(10) C(9) 0.1(13) . . . . no
C(7) S(1) C(10) C(11) -179.8(14) . . . . no
C(7) N(1) C(1) C(2) 15(3) . . . . no
C(7) N(1) C(1) C(6) -165.2(17) . . . . no
C(1) N(1) C(7) S(1) 39(2) . . . . no
C(1) N(1) C(7) C(8) -141.0(17) . . . . no
O(1) N(3) C(6) C(1) 161(3) . . . . no
O(1) N(3) C(6) C(5) -19(4) . . . . no
O(2) N(3) C(6) C(1) -19(4) . . . . no
O(2) N(3) C(6) C(5) 161(3) . . . . no
N(1) C(1) C(2) C(3) -180(3) . . . . no
C(6) C(1) C(2) C(3) 0(4) . . . . no
N(1) C(1) C(6) N(3) 0(3) . . . . no
N(1) C(1) C(6) C(5) -180(2) . . . . no
C(2) C(1) C(6) N(3) -180(2) . . . . no
C(2) C(1) C(6) C(5) 0(4) . . . . no
C(1) C(2) C(3) C(4) 0(5) . . . . no
C(2) C(3) C(4) C(5) 0(5) . . . . no
C(3) C(4) C(5) C(6) 0(5) . . . . no
_exptl_crystal_colour            Orange
_exptl_crystal_recrystallization_method 'Used as supplied'
####################################################################### 
# 
# 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_OP_1p630GPa
_database_code_depnum_ccdc_archive 'CCDC 1878584'
_audit_update_record             
;
2018-11-13 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT340_ROY_OP_1p630GPa     
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.02236 Ang. 
RESPONSE: Much of the intramolecular geometry was held fixed to known bond distances and angles (CSD: QAXMEH03)- these are not expected to change  significantly over the course of compression. Please see the main manuscript for discussion of intramolecular geometry
;
_vrf_PLAT430_ROY_OP_1p630GPa     
;
PROBLEM: Short Inter D...A Contact O2 ..N2 . 2.79 Ang.
RESPONSE: These are high pressure data - short contacts are to be expected
;
_vrf_PLAT413_ROY_OP_1p630GPa     
;
PROBLEM: Short Inter XH3 .. XHn H4 ..H113 . 2.04 Ang.
RESPONSE: Wood et al (CrystEngComm, 2008, 10, 368-376) have shown that the lower limit for H...H contacts in high-pressure structures is 1.7 A.
;

_chemical_name_systematic        
;
5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
;
_chemical_name_common            ROY
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 N3 O2 S1'

_chemical_formula_structural     ?
_chemical_formula_sum            'C12 H9 N3 O2 S1'
_chemical_formula_iupac          ?
_chemical_formula_weight         259.28
_chemical_compound_source        'TCI Chemicals'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   7.2068(6)
_cell_length_b                   13.153(2)
_cell_length_c                   11.3365(16)
_cell_angle_alpha                90
_cell_angle_beta                 102.812(11)
_cell_angle_gamma                90
_cell_volume                     1047.8(3)
_cell_formula_units_Z            4

_cell_measurement_temperature    295
_cell_measurement_pressure       1.630(6) #GPa

_cell_special_details            
;
Cell parameters included in refinement
;

_exptl_crystal_density_diffrn    1.644

_pd_spec_mounting                'TiZr Capsule'
_pd_spec_mount_mode              transmission
_pd_char_colour                  Orange
_chemical_absolute_configuration .

_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
Calculated using MANTID routines.
;

_pd_instr_location               
'ISIS Neutron Facility, Rutherford Appleton Laboratory'
_diffrn_ambient_temperature      295
_diffrn_source                   'Pulsed neutron source'
_diffrn_source_target            W
_diffrn_radiation_type           Neutron
_diffrn_measurement_device_type  'PEARL diffractometer'
_diffrn_radiation_monochromator  none
_diffrn_detector                 'ZnS scintillator'
_diffrn_detector_type            custom

_pd_meas_scan_method             Time-of-flight
_pd_meas_special_details         
;
Time of flight method using a pulsed neutron source
;

# The following three items are used for time-of-flight measurements only.

_pd_instr_dist_src/spec          12800
_pd_instr_dist_spec/detc         800
_pd_meas_2theta_fixed            90

_pd_proc_ls_profile_function     
;
Voigt function convoluted with a back-to-back double exponential.
;

_pd_proc_ls_background_function  'Chebychev polynomial'

_pd_proc_ls_pref_orient_corr     
;
No requirement for preferred orientation correction
;

_pd_proc_ls_prof_R_factor        7.112
_pd_proc_ls_prof_wR_factor       2.014
_pd_proc_ls_prof_R_expected      2.175
_refine_ls_goodness_of_fit_all   0.834
_refine_ls_R_I_factor            1.147

_refine_ls_matrix_type           sparse
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     56
_refine_ls_number_restraints     4
_refine_ls_number_constraints    ?
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_shift/su_max          <0.001

_pd_proc_info_excluded_regions   
;
?

;
_pd_proc_info_data_reduction     
;
Custom ISIS software
;

_refine_special_details          
;The refinement used DFT-optimised structures as a source of restraint on 

torsion angles. A Z-matrix was used, so that distances, angles and 

torsions were refined. Please see the manuscript for a full description 

of refinement details.



Check-cif alerts



PROBLEM: _diffrn_radiation_wavelength is missing

PROBLEM: No Wavelength found in CIF - 0.71073 Ang Assumed     Please Check

RESPONSE: The time of flight method was used





PROBLEM: Short Inter D...A Contact  O2     ..  N2      ..       2.79 Ang. 

PROBLEM: Short Inter XH3 .. XHn     H4     ..  H113    ..       2.04 Ang.  

PROBLEM: Short Inter X...Y Contact  O2     ..  C12     ..       2.93 Ang.  

RESPONSE: These are high pressure data - short contacts are to be 

expected





PROBLEM: _atom_site_U_iso_or_equiv is missing

RESPONSE: Topas outputs atomic displacement parameters expressed as 'B' instead

of 'U'. Isotropic B values are given below.





PROBLEM; Low Bond Precision on  C-C Bonds ...............    0.02236 Ang.  

PROBLEM: Bond    Calc   1.728(17), Rep     1.72800 ......    Missing s.u.  

PROBLEM: Angle   Calc     92.5(8), Rep       92.50 ......    Missing s.u.  

PROBLEM: Torsion Calc  -179.9(14), Rep     -180.00 ......    Missing s.u.  

(Numerous)



RESPONSE: Much of the intramolecular geometry was held fixed to known

bond distances and angles (CSD: QAXMEH03)- these are not expected to change 

significantly over the course of compression. Please see the main manuscript

for discussion of intramolecular geometry.,The molecular geometry was refined using a constrained and restrained rigid body, using a Z-matrix formalism. Please see main manuscript for full details.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
N1 N 4 -0.017(2) 0.6741(9) 0.6578(8) 1 0.72(10)
N2 N 4 -0.2283(17) 0.4988(8) 0.4122(8) 1 0.72(10)
N3 N 4 0.084(5) 0.5667(16) 0.8757(8) 1 0.72(10)
O1 O 4 0.178(7) 0.534(2) 0.9721(11) 1 0.72(10)
O2 O 4 0.053(6) 0.5154(14) 0.7828(11) 1 0.72(10)
S1 S 4 0.059(3) 0.8441(8) 0.5338(12) 1 0.72(10)
C1 C 4 -0.041(4) 0.7200(11) 0.7633(11) 1 0.72(10)
C2 C 4 -0.114(5) 0.8176(13) 0.7599(16) 1 0.72(10)
C3 C 4 -0.138(7) 0.8636(16) 0.865(2) 1 0.72(10)
C4 C 4 -0.089(7) 0.8118(17) 0.9744(17) 1 0.72(10)
C5 C 4 -0.016(6) 0.7142(16) 0.9777(12) 1 0.72(10)
C6 C 4 0.008(4) 0.6683(14) 0.8722(9) 1 0.72(10)
C7 C 4 -0.022(2) 0.7221(8) 0.5484(9) 1 0.72(10)
C8 C 4 -0.091(2) 0.6799(7) 0.4378(9) 1 0.72(10)
C9 C 4 -0.079(2) 0.7464(7) 0.3401(10) 1 0.72(10)
C10 C 4 -0.001(3) 0.8382(7) 0.3778(12) 1 0.72(10)
C11 C 4 0.036(3) 0.9266(8) 0.3038(15) 1 0.72(10)
C12 C 4 -0.1674(17) 0.5791(8) 0.4236(8) 1 0.72(10)
H1 H 4 0.012(7) 0.5997(12) 0.6570(13) 1 0.86(12)
H2 H 4 -0.149(6) 0.8550(15) 0.681(2) 1 0.86(12)
H3 H 4 -0.190(9) 0.934(2) 0.863(2) 1 0.86(12)
H4 H 4 -0.106(8) 0.845(2) 1.051(2) 1 0.86(12)
H5 H 4 0.019(6) 0.677(2) 1.0564(16) 1 0.86(12)
H9 H 4 -0.123(3) 0.7275(9) 0.2530(17) 1 0.86(12)
H111 H 4 -0.033(5) 0.9877(13) 0.325(3) 1 0.86(12)
H112 H 4 0.175(4) 0.9409(17) 0.321(2) 1 0.86(12)
H113 H 4 -0.011(5) 0.9107(13) 0.216(2) 1 0.86(12)


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S(1) C(7) 1.728(17) . . no
S(1) C(10) 1.727(19) . . no
O(1) N(3) 1.23(3) . . no
O(2) N(3) 1.23(2) . . no
N(1) C(1) 1.384(18) . . no
N(1) C(7) 1.385(14) . . no
N(2) C(12) 1.140(15) . . no
N(3) C(6) 1.44(3) . . no
C(1) C(2) 1.39(3) . . no
C(1) C(6) 1.385(18) . . no
C(2) C(3) 1.38(3) . . no
C(3) C(4) 1.39(3) . . no
C(4) C(5) 1.39(4) . . no
C(5) C(6) 1.38(2) . . no
C(7) C(8) 1.361(14) . . no
C(8) C(9) 1.429(15) . . no
C(8) C(12) 1.431(15) . . no
C(9) C(10) 1.360(16) . . no
C(10) C(11) 1.492(18) . . no
N(1) H(1) 1.00(2) . . no
C(2) H(2) 1.00(3) . . no
C(3) H(3) 1.00(4) . . no
C(4) H(4) 1.00(4) . . no
C(5) H(5) 1.00(3) . . no
C(9) H(9) 1.00(2) . . no
C(11) H(111) 1.00(3) . . no
C(11) H(112) 1.00(4) . . no
C(11) H(113) 1.00(3) . . no


loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(7) S(1) C(10) 92.5(8) . . . no
C(1) N(1) C(7) 126.3(11) . . . no
O(1) N(3) O(2) 122(3) . . . no
O(1) N(3) C(6) 118.7(17) . . . no
O(2) N(3) C(6) 119.3(18) . . . no
N(1) C(1) C(2) 120.0(13) . . . no
N(1) C(1) C(6) 120.0(15) . . . no
C(2) C(1) C(6) 120.0(16) . . . no
C(1) C(2) C(3) 120.1(17) . . . no
C(2) C(3) C(4) 120(2) . . . no
C(3) C(4) C(5) 120(2) . . . no
C(4) C(5) C(6) 120.0(16) . . . no
N(3) C(6) C(1) 120.0(13) . . . no
N(3) C(6) C(5) 120.0(13) . . . no
C(1) C(6) C(5) 120.0(19) . . . no
S(1) C(7) N(1) 124.5(9) . . . no
S(1) C(7) C(8) 110.7(9) . . . no
N(1) C(7) C(8) 124.8(10) . . . no
C(7) C(8) C(9) 113.1(9) . . . no
C(7) C(8) C(12) 122.3(9) . . . no
C(9) C(8) C(12) 124.6(9) . . . no
C(8) C(9) C(10) 113.1(10) . . . no
S(1) C(10) C(9) 110.7(10) . . . no
S(1) C(10) C(11) 120.4(10) . . . no
C(9) C(10) C(11) 128.9(12) . . . no
N(2) C(12) C(8) 180.0(16) . . . no
C(1) N(1) H(1) 120.0(15) . . . no
C(7) N(1) H(1) 113.7(15) . . . no
C(1) C(2) H(2) 120(2) . . . no
C(3) C(2) H(2) 120(3) . . . no
C(2) C(3) H(3) 120(2) . . . no
C(4) C(3) H(3) 120(3) . . . no
C(3) C(4) H(4) 120(3) . . . no
C(5) C(4) H(4) 120(2) . . . no
C(4) C(5) H(5) 120(3) . . . no
C(6) C(5) H(5) 120(3) . . . no
C(8) C(9) H(9) 123.6(13) . . . no
C(10) C(9) H(9) 123.4(13) . . . no
C(10) C(11) H(111) 109(2) . . . no
C(10) C(11) H(112) 110(2) . . . no
C(10) C(11) H(113) 109.5(17) . . . no
H(111) C(11) H(112) 110(3) . . . no
H(111) C(11) H(113) 109(3) . . . no
H(112) C(11) H(113) 110(3) . . . no


loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C(10) S(1) C(7) N(1) -179.9(14) . . . . no
C(10) S(1) C(7) C(8) 0.1(16) . . . . no
C(7) S(1) C(10) C(9) -0.1(17) . . . . no
C(7) S(1) C(10) C(11) -179.7(17) . . . . no
C(7) N(1) C(1) C(2) 14(4) . . . . no
C(7) N(1) C(1) C(6) -166(2) . . . . no
C(1) N(1) C(7) S(1) 34(3) . . . . no
C(1) N(1) C(7) C(8) -145.6(19) . . . . no
O(1) N(3) C(6) C(1) 158(4) . . . . no
O(1) N(3) C(6) C(5) -22(5) . . . . no
O(2) N(3) C(6) C(1) -22(5) . . . . no
O(2) N(3) C(6) C(5) 158(4) . . . . no
N(1) C(1) C(2) C(3) -180(3) . . . . no
C(6) C(1) C(2) C(3) 0(5) . . . . no
N(1) C(1) C(6) N(3) 0(4) . . . . no
N(1) C(1) C(6) C(5) 180(3) . . . . no
C(2) C(1) C(6) N(3) -180(3) . . . . no
C(2) C(1) C(6) C(5) 0(4) . . . . no
C(1) C(2) C(3) C(4) 0(6) . . . . no
C(2) C(3) C(4) C(5) 0(7) . . . . no
C(3) C(4) C(5) C(6) 0(7) . . . . no
_exptl_crystal_colour            Orange
_exptl_crystal_recrystallization_method 'Used as supplied'
####################################################################### 
# 
# 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_OP_0p975GPa
_database_code_depnum_ccdc_archive 'CCDC 1878583'
_audit_update_record             
;
2018-11-13 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT340_ROY_OP_0p975GPa     
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.01764 Ang. 
RESPONSE: Much of the intramolecular geometry was held fixed to known bond distances and angles (CSD: QAXMEH03)- these are not expected to change  significantly over the course of compression. Please see the main manuscript for discussion of intramolecular geometry
;
_vrf_PLAT430_ROY_OP_0p975GPa     
;
PROBLEM: Short Inter D...A Contact O2 ..N2 . 2.78 Ang.
RESPONSE: These are high pressure data - short contacts are to be expected
;
_vrf_PLAT413_ROY_OP_0p975GPa     
;
PROBLEM: Short Inter XH3 .. XHn H4 ..H113 . 2.05 Ang.
RESPONSE: Wood et al (CrystEngComm, 2008, 10, 368-376) have shown that the lower limit for H...H contacts in high-pressure structures is 1.7 A.
;

_chemical_name_systematic        
;
5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
;
_chemical_name_common            ROY
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 N3 O2 S1'

_chemical_formula_structural     ?
_chemical_formula_sum            'C12 H9 N3 O2 S1'
_chemical_formula_iupac          ?
_chemical_formula_weight         259.28
_chemical_compound_source        'TCI Chemicals'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   7.4126(4)
_cell_length_b                   13.2122(15)
_cell_length_c                   11.4253(11)
_cell_angle_alpha                90
_cell_angle_beta                 103.122(8)
_cell_angle_gamma                90
_cell_volume                     1089.73(17)
_cell_formula_units_Z            4

_cell_measurement_temperature    295
_cell_measurement_pressure       0.975(5) #GPa

_cell_special_details            
;
Cell parameters included in refinement
;

_exptl_crystal_density_diffrn    1.580

_pd_spec_mounting                'TiZr Capsule'
_pd_spec_mount_mode              transmission
_pd_char_colour                  Orange
_chemical_absolute_configuration .

_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
Calculated using MANTID routines.
;

_pd_instr_location               
'ISIS Neutron Facility, Rutherford Appleton Laboratory'
_diffrn_ambient_temperature      295
_diffrn_source                   'Pulsed neutron source'
_diffrn_source_target            W
_diffrn_radiation_type           Neutron
_diffrn_measurement_device_type  'PEARL diffractometer'
_diffrn_radiation_monochromator  none
_diffrn_detector                 'ZnS scintillator'
_diffrn_detector_type            custom

_pd_meas_scan_method             Time-of-flight
_pd_meas_special_details         
;
Time of flight method using a pulsed neutron source
;

# The following three items are used for time-of-flight measurements only.

_pd_instr_dist_src/spec          12800
_pd_instr_dist_spec/detc         800
_pd_meas_2theta_fixed            90

_pd_proc_ls_profile_function     
;
Voigt function convoluted with a back-to-back double exponential.
;

_pd_proc_ls_background_function  'Chebychev polynomial'

_pd_proc_ls_pref_orient_corr     
;
No requirement for preferred orientation correction
;

_pd_proc_ls_prof_R_factor        2.356
_pd_proc_ls_prof_wR_factor       1.870
_pd_proc_ls_prof_R_expected      2.407
_refine_ls_goodness_of_fit_all   0.777
_refine_ls_R_I_factor            1.250

_refine_ls_matrix_type           sparse
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     49
_refine_ls_number_restraints     4
_refine_ls_number_constraints    ?
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_shift/su_max          <0.001

_pd_proc_info_excluded_regions   
;
?

;
_pd_proc_info_data_reduction     
;
Custom ISIS software
;

_refine_special_details          
;The refinement used DFT-optimised structures as a source of restraint on 

torsion angles. A Z-matrix was used, so that distances, angles and 

torsions were refined. Please see the manuscript for a full description 

of refinement details.



Check-cif alerts



PROBLEM:  _diffrn_radiation_wavelength is missing

PROBLEM: No Wavelength found in CIF - 0.71073 Ang Assumed     Please Check

RESPONSE: The time of flight method was used





PROBLEM: Short Inter D...A Contact  O2     ..  N2      ..       2.78 Ang

PROBLEM: Short Inter XH3 .. XHn     H4     ..  H113    ..       2.05 Ang.

PROBLEM: Short Inter X...Y Contact  O2     ..  C12     ..       2.93 Ang.  



RESPONSE: These are high pressure data - short contacts are to be 

expected





PROBLEM: _atom_site_U_iso_or_equiv is missing

RESPONSE: Topas outputs atomic displacement parameters expressed as 'B' instead

of 'U'. Isotropic B values are given below.





Low Bond Precision on  C-C Bonds ...............    0.01764 Ang. 

PROBLEM: Bond    Calc   1.728(13), Rep     1.72800 ......    Missing s.u.  

PROBLEM: Angle   Calc     92.5(6), Rep       92.50 ......    Missing s.u.  

PROBLEM: Torsion Calc     0.2(12), Rep        0.00 ......    Missing s.u.  

(Numerous)



RESPONSE: Much of the intramolecular geometry was held fixed to known

bond distances and angles (CSD: QAXMEH03)- these are not expected to change 

significantly over the course of compression. Please see the main manuscript

for discussion of intramolecular geometry.,The molecular geometry was refined using a constrained and restrained rigid body, using a Z-matrix formalism. Please see main manuscript for full details.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
N1 N 4 -0.0138(17) 0.6735(7) 0.6569(6) 1 0.75(8)
N2 N 4 -0.2259(12) 0.5002(6) 0.4127(6) 1 0.75(8)
N3 N 4 0.084(3) 0.5671(12) 0.8738(6) 1 0.75(8)
O1 O 4 0.171(5) 0.5334(17) 0.9705(8) 1 0.75(8)
O2 O 4 0.058(4) 0.5167(11) 0.7809(8) 1 0.75(8)
S1 S 4 0.064(2) 0.8418(6) 0.5338(9) 1 0.75(8)
C1 C 4 -0.037(3) 0.7195(9) 0.7613(8) 1 0.75(8)
C2 C 4 -0.108(4) 0.8168(10) 0.7574(12) 1 0.75(8)
C3 C 4 -0.132(5) 0.8627(12) 0.8619(15) 1 0.75(8)
C4 C 4 -0.084(5) 0.8115(13) 0.9703(13) 1 0.75(8)
C5 C 4 -0.013(4) 0.7142(12) 0.9742(9) 1 0.75(8)
C6 C 4 0.010(3) 0.6682(11) 0.8697(7) 1 0.75(8)
C7 C 4 -0.0183(16) 0.7212(6) 0.5483(7) 1 0.75(8)
C8 C 4 -0.0876(14) 0.6794(6) 0.4383(7) 1 0.75(8)
C9 C 4 -0.0747(16) 0.7453(6) 0.3413(8) 1 0.75(8)
C10 C 4 0.004(2) 0.8361(6) 0.3788(9) 1 0.75(8)
C11 C 4 0.041(2) 0.9236(6) 0.3054(11) 1 0.75(8)
C12 C 4 -0.1646(12) 0.5797(6) 0.4241(6) 1 0.75(8)
H1 H 4 0.013(6) 0.5993(9) 0.6561(11) 1 0.90(9)
H2 H 4 -0.144(4) 0.8552(12) 0.6761(17) 1 0.90(9)
H3 H 4 -0.185(6) 0.9357(17) 0.8589(18) 1 0.90(9)
H4 H 4 -0.102(6) 0.8460(15) 1.0487(18) 1 0.90(9)
H5 H 4 0.022(5) 0.6757(15) 1.0555(13) 1 0.90(9)
H9 H 4 -0.1209(18) 0.7258(7) 0.2513(13) 1 0.90(9)
H111 H 4 -0.017(4) 0.9887(11) 0.3326(19) 1 0.90(9)
H112 H 4 0.183(3) 0.9334(13) 0.317(2) 1 0.90(9)
H113 H 4 -0.018(4) 0.9099(10) 0.2152(16) 1 0.90(9)


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S(1) C(7) 1.728(13) . . no
S(1) C(10) 1.727(14) . . no
O(1) N(3) 1.23(2) . . no
O(2) N(3) 1.231(15) . . no
N(1) C(1) 1.384(14) . . no
N(1) C(7) 1.385(11) . . no
N(2) C(12) 1.140(11) . . no
N(3) C(6) 1.44(2) . . no
C(1) C(2) 1.39(2) . . no
C(1) C(6) 1.385(14) . . no
C(2) C(3) 1.39(3) . . no
C(3) C(4) 1.39(2) . . no
C(4) C(5) 1.39(3) . . no
C(5) C(6) 1.384(18) . . no
C(7) C(8) 1.362(11) . . no
C(8) C(9) 1.430(12) . . no
C(8) C(12) 1.430(12) . . no
C(9) C(10) 1.360(13) . . no
C(10) C(11) 1.490(14) . . no
N(1) H(1) 1.001(18) . . no
C(2) H(2) 1.04(2) . . no
C(3) H(3) 1.04(3) . . no
C(4) H(4) 1.04(3) . . no
C(5) H(5) 1.04(2) . . no
C(9) H(9) 1.040(17) . . no
C(11) H(111) 1.04(2) . . no
C(11) H(112) 1.04(3) . . no
C(11) H(113) 1.04(2) . . no


loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(7) S(1) C(10) 92.5(6) . . . no
C(1) N(1) C(7) 126.1(9) . . . no
O(1) N(3) O(2) 121.8(19) . . . no
O(1) N(3) C(6) 118.9(13) . . . no
O(2) N(3) C(6) 119.3(12) . . . no
N(1) C(1) C(2) 120.0(10) . . . no
N(1) C(1) C(6) 120.0(12) . . . no
C(2) C(1) C(6) 120.0(12) . . . no
C(1) C(2) C(3) 120.0(13) . . . no
C(2) C(3) C(4) 120.0(18) . . . no
C(3) C(4) C(5) 120.0(16) . . . no
C(4) C(5) C(6) 120.0(12) . . . no
N(3) C(6) C(1) 120.0(10) . . . no
N(3) C(6) C(5) 120.0(10) . . . no
C(1) C(6) C(5) 120.1(14) . . . no
S(1) C(7) N(1) 124.6(7) . . . no
S(1) C(7) C(8) 110.7(7) . . . no
N(1) C(7) C(8) 124.7(8) . . . no
C(7) C(8) C(9) 113.0(8) . . . no
C(7) C(8) C(12) 122.4(7) . . . no
C(9) C(8) C(12) 124.6(7) . . . no
C(8) C(9) C(10) 113.1(8) . . . no
S(1) C(10) C(9) 110.7(8) . . . no
S(1) C(10) C(11) 120.4(8) . . . no
C(9) C(10) C(11) 128.9(9) . . . no
N(2) C(12) C(8) 179.9(13) . . . no
C(1) N(1) H(1) 120.1(12) . . . no
C(7) N(1) H(1) 113.7(12) . . . no
C(1) C(2) H(2) 120.0(17) . . . no
C(3) C(2) H(2) 120.0(19) . . . no
C(2) C(3) H(3) 120.0(19) . . . no
C(4) C(3) H(3) 120(2) . . . no
C(3) C(4) H(4) 120(2) . . . no
C(5) C(4) H(4) 120.1(18) . . . no
C(4) C(5) H(5) 119.9(19) . . . no
C(6) C(5) H(5) 120(2) . . . no
C(8) C(9) H(9) 123.4(10) . . . no
C(10) C(9) H(9) 123.5(10) . . . no
C(10) C(11) H(111) 109.4(17) . . . no
C(10) C(11) H(112) 109.6(15) . . . no
C(10) C(11) H(113) 109.5(13) . . . no
H(111) C(11) H(112) 110(2) . . . no
H(111) C(11) H(113) 109(2) . . . no
H(112) C(11) H(113) 110(2) . . . no


loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C(10) S(1) C(7) N(1) -180.0(11) . . . . no
C(10) S(1) C(7) C(8) 0.2(12) . . . . no
C(7) S(1) C(10) C(9) -0.2(13) . . . . no
C(7) S(1) C(10) C(11) 180.0(12) . . . . no
C(7) N(1) C(1) C(2) 14(3) . . . . no
C(7) N(1) C(1) C(6) -166.0(16) . . . . no
C(1) N(1) C(7) S(1) 35(2) . . . . no
C(1) N(1) C(7) C(8) -144.9(15) . . . . no
O(1) N(3) C(6) C(1) 160(3) . . . . no
O(1) N(3) C(6) C(5) -19(4) . . . . no
O(2) N(3) C(6) C(1) -20(3) . . . . no
O(2) N(3) C(6) C(5) 160(3) . . . . no
N(1) C(1) C(2) C(3) 180(2) . . . . no
C(6) C(1) C(2) C(3) 0(4) . . . . no
N(1) C(1) C(6) N(3) 0(3) . . . . no
N(1) C(1) C(6) C(5) 180(2) . . . . no
C(2) C(1) C(6) N(3) -180(2) . . . . no
C(2) C(1) C(6) C(5) 0(3) . . . . no
C(1) C(2) C(3) C(4) 0(5) . . . . no
C(2) C(3) C(4) C(5) 0(5) . . . . no
C(3) C(4) C(5) C(6) 0(5) . . . . no
_exptl_crystal_colour            Orange
_exptl_crystal_recrystallization_method 'Used as supplied'
####################################################################### 
# 
# 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_OP_2p629GPa
_database_code_depnum_ccdc_archive 'CCDC 1878585'
_audit_update_record             
;
2018-11-13 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT413_ROY_OP_2p629GPa     
;
PROBLEM: Short Inter XH3 .. XHn H4 ..H113 . 1.83 Ang.
RESPONSE: Wood et al (CrystEngComm, 2008, 10, 368-376) have shown that the lower limit for H...H contacts in high-pressure structures is 1.7 A.
;
_vrf_PLAT340_ROY_OP_2p629GPa     
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.01927 Ang. 
RESPONSE: Much of the intramolecular geometry was held fixed to known bond distances and angles (CSD: QAXMEH03)- these are not expected to change  significantly over the course of compression. Please see the main manuscript for discussion of intramolecular geometry
;
_vrf_PLAT430_ROY_OP_2p629GPa     
;
PROBLEM: Short Inter D...A Contact O1 ..O1 . 2.74 Ang.
RESPONSE: These are high pressure data - short contacts are to be expected
;
_vrf_PLAT430_ROY_OP_2p629GPa_2   
;
PROBLEM: Short Inter D...A Contact O2 ..N2 . 2.85 Ang.
RESPONSE: These are high pressure data - short contacts are to be expected
;

_chemical_name_systematic        
;
5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
;
_chemical_name_common            ROY
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 N3 O2 S1'

_chemical_formula_structural     ?
_chemical_formula_sum            'C12 H9 N3 O2 S1'
_chemical_formula_iupac          ?
_chemical_formula_weight         259.28
_chemical_compound_source        'TCI Chemicals'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   6.9954(5)
_cell_length_b                   13.0631(18)
_cell_length_c                   11.2417(13)
_cell_angle_alpha                90
_cell_angle_beta                 102.703(9)
_cell_angle_gamma                90
_cell_volume                     1002.1(2)
_cell_formula_units_Z            4

_cell_measurement_temperature    295
_cell_measurement_pressure       2.628(6) #GPa

_cell_special_details            
;
Cell parameters included in refinement
;

_exptl_crystal_density_diffrn    1.719

_pd_spec_mounting                'TiZr Capsule'
_pd_spec_mount_mode              transmission
_pd_char_colour                  Orange
_chemical_absolute_configuration .

_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
Calculated using MANTID routines.
;

_pd_instr_location               
'ISIS Neutron Facility, Rutherford Appleton Laboratory'
_diffrn_ambient_temperature      295
_diffrn_source                   'Pulsed neutron source'
_diffrn_source_target            W
_diffrn_radiation_type           Neutron
_diffrn_measurement_device_type  'PEARL diffractometer'
_diffrn_radiation_monochromator  none
_diffrn_detector                 'ZnS scintillator'
_diffrn_detector_type            custom

_pd_meas_scan_method             Time-of-flight
_pd_meas_special_details         
;
Time of flight method using a pulsed neutron source
;

# The following three items are used for time-of-flight measurements only.

_pd_instr_dist_src/spec          12800
_pd_instr_dist_spec/detc         800
_pd_meas_2theta_fixed            90

_pd_proc_ls_profile_function     
;
Voigt function convoluted with a back-to-back double exponential.
;

_pd_proc_ls_background_function  'Chebychev polynomial'

_pd_proc_ls_pref_orient_corr     
;
No requirement for preferred orientation correction
;

_pd_proc_ls_prof_R_factor        4.672
_pd_proc_ls_prof_wR_factor       1.796
_pd_proc_ls_prof_R_expected      1.437
_refine_ls_goodness_of_fit_all   1.063
_refine_ls_R_I_factor            1.558

_refine_ls_matrix_type           sparse
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     56
_refine_ls_number_restraints     4
_refine_ls_number_constraints    ?
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_shift/su_max          <0.001

_pd_proc_info_excluded_regions   
;
?

;
_pd_proc_info_data_reduction     
;
Custom ISIS software
;

_refine_special_details          
;The refinement used DFT-optimised structures as a source of restraint on 

torsion angles. A Z-matrix was used, so that distances, angles and 

torsions were refined. Please see the manuscript for a full description 

of refinement details.



Check-cif alerts



PROBLEM: _diffrn_radiation_wavelength is missing

PROBLEM: No Wavelength found in CIF - 0.71073 Ang Assumed     Please Check

RESPONSE: The time of flight method was used





PROBLEM: Short Inter D...A Contact  O1     ..  O1      ..       2.74 Ang. 

PROBLEM: Short Inter D...A Contact  O2     ..  N2      ..       2.85 Ang.   

PROBLEM: Short Inter X...Y Contact  S1     ..  C5      ..       3.20 Ang.  

PROBLEM: Short Inter X...Y Contact  O2     ..  C12     ..       2.90 Ang.  

PROBLEM: Short Inter X...Y Contact  N2     ..  C11     ..       3.02 Ang.  

PROBLEM: Short Inter X...Y Contact  N2     ..  C4      ..       3.04 Ang.  

PROBLEM: Short Inter X...Y Contact  C3     ..  C12     ..       3.20 Ang.  

RESPONSE: These are high pressure data - short contacts are to be 

expected





PROBLEM: _atom_site_U_iso_or_equiv is missing

RESPONSE: Topas outputs atomic displacement parameters expressed as 'B' instead

of 'U'. Isotropic B values are given below.





PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01927 Ang. 

PROBLEM: Bond    Calc   1.727(14), Rep     1.72700 ......    Missing s.u.  

PROBLEM: Angle   Calc     92.5(7), Rep       92.50 ......    Missing s.u.  

PROBLEM: Torsion Calc  -179.8(14), Rep     -180.00 ......    Missing s.u.  

(Numerous)



RESPONSE: Much of the intramolecular geometry was held fixed to known

bond distances and angles (CSD: QAXMEH03)- these are not expected to change 

significantly over the course of compression. Please see the main manuscript

for discussion of intramolecular geometry.,The molecular geometry was refined using a constrained and restrained rigid body, using a Z-matrix formalism. Please see main manuscript for full details.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
N1 N 4 -0.019(2) 0.6694(8) 0.6583(8) 1 0.51(10)
N2 N 4 -0.2378(16) 0.4918(7) 0.4123(7) 1 0.51(10)
N3 N 4 0.080(5) 0.5627(14) 0.8790(7) 1 0.51(10)
O1 O 4 0.176(6) 0.529(2) 0.9761(10) 1 0.51(10)
O2 O 4 0.044(5) 0.5102(12) 0.7859(10) 1 0.51(10)
S1 S 4 0.068(3) 0.8379(6) 0.5318(11) 1 0.51(10)
C1 C 4 -0.039(3) 0.7178(10) 0.7645(10) 1 0.51(10)
C2 C 4 -0.107(5) 0.8176(11) 0.7605(15) 1 0.51(10)
C3 C 4 -0.126(7) 0.8661(14) 0.8668(19) 1 0.51(10)
C4 C 4 -0.078(7) 0.8147(15) 0.9771(16) 1 0.51(10)
C5 C 4 -0.010(6) 0.7149(14) 0.9811(11) 1 0.51(10)
C6 C 4 0.009(4) 0.6664(12) 0.8748(8) 1 0.51(10)
C7 C 4 -0.020(2) 0.7163(6) 0.5476(8) 1 0.51(10)
C8 C 4 -0.0909(18) 0.6729(5) 0.4365(8) 1 0.51(10)
C9 C 4 -0.074(2) 0.7384(6) 0.3374(9) 1 0.51(10)
C10 C 4 0.009(3) 0.8304(5) 0.3746(11) 1 0.51(10)
C11 C 4 0.051(3) 0.9179(6) 0.2992(13) 1 0.51(10)
C12 C 4 -0.1726(16) 0.5721(6) 0.4230(7) 1 0.51(10)
H1 H 4 0.003(7) 0.5938(9) 0.6579(12) 1 0.62(12)
H2 H 4 -0.142(6) 0.8556(13) 0.679(2) 1 0.62(12)
H3 H 4 -0.177(9) 0.9398(19) 0.864(2) 1 0.62(12)
H4 H 4 -0.093(8) 0.8504(17) 1.056(2) 1 0.62(12)
H5 H 4 0.025(6) 0.6769(18) 1.0626(15) 1 0.62(12)
H9 H 4 -0.119(2) 0.7181(7) 0.2478(15) 1 0.62(12)
H111 H 4 -0.033(5) 0.9795(13) 0.312(3) 1 0.62(12)
H112 H 4 0.196(4) 0.9370(17) 0.325(2) 1 0.62(12)
H113 H 4 0.018(5) 0.8976(11) 0.2092(18) 1 0.62(12)


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S(1) C(7) 1.727(14) . . no
S(1) C(10) 1.727(17) . . no
O(1) N(3) 1.23(3) . . no
O(2) N(3) 1.230(17) . . no
N(1) C(1) 1.385(16) . . no
N(1) C(7) 1.386(13) . . no
N(2) C(12) 1.140(13) . . no
N(3) C(6) 1.44(3) . . no
C(1) C(2) 1.39(2) . . no
C(1) C(6) 1.385(16) . . no
C(2) C(3) 1.39(3) . . no
C(3) C(4) 1.39(3) . . no
C(4) C(5) 1.39(3) . . no
C(5) C(6) 1.39(2) . . no
C(7) C(8) 1.362(12) . . no
C(8) C(9) 1.430(13) . . no
C(8) C(12) 1.430(11) . . no
C(9) C(10) 1.360(14) . . no
C(10) C(11) 1.490(16) . . no
N(1) H(1) 1.000(18) . . no
C(2) H(2) 1.02(3) . . no
C(3) H(3) 1.03(4) . . no
C(4) H(4) 1.03(3) . . no
C(5) H(5) 1.02(2) . . no
C(9) H(9) 1.022(19) . . no
C(11) H(111) 1.03(3) . . no
C(11) H(112) 1.02(3) . . no
C(11) H(113) 1.02(2) . . no


loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(7) S(1) C(10) 92.5(7) . . . no
C(1) N(1) C(7) 126.2(10) . . . no
O(1) N(3) O(2) 122(2) . . . no
O(1) N(3) C(6) 118.9(15) . . . no
O(2) N(3) C(6) 119.5(16) . . . no
N(1) C(1) C(2) 120.1(12) . . . no
N(1) C(1) C(6) 120.0(13) . . . no
C(2) C(1) C(6) 120.0(13) . . . no
C(1) C(2) C(3) 120.0(15) . . . no
C(2) C(3) C(4) 120(2) . . . no
C(3) C(4) C(5) 120.0(19) . . . no
C(4) C(5) C(6) 120.0(14) . . . no
N(3) C(6) C(1) 120.0(11) . . . no
N(3) C(6) C(5) 120.0(12) . . . no
C(1) C(6) C(5) 120.0(16) . . . no
S(1) C(7) N(1) 124.6(8) . . . no
S(1) C(7) C(8) 110.8(8) . . . no
N(1) C(7) C(8) 124.6(9) . . . no
C(7) C(8) C(9) 112.9(8) . . . no
C(7) C(8) C(12) 122.5(8) . . . no
C(9) C(8) C(12) 124.6(8) . . . no
C(8) C(9) C(10) 113.1(9) . . . no
S(1) C(10) C(9) 110.8(9) . . . no
S(1) C(10) C(11) 120.4(9) . . . no
C(9) C(10) C(11) 128.8(11) . . . no
N(2) C(12) C(8) 180.0(15) . . . no
C(1) N(1) H(1) 120.0(14) . . . no
C(7) N(1) H(1) 113.8(14) . . . no
C(1) C(2) H(2) 120(2) . . . no
C(3) C(2) H(2) 120(2) . . . no
C(2) C(3) H(3) 120(2) . . . no
C(4) C(3) H(3) 120(3) . . . no
C(3) C(4) H(4) 120(3) . . . no
C(5) C(4) H(4) 120(2) . . . no
C(4) C(5) H(5) 120(2) . . . no
C(6) C(5) H(5) 120(2) . . . no
C(8) C(9) H(9) 123.5(10) . . . no
C(10) C(9) H(9) 123.4(11) . . . no
C(10) C(11) H(111) 109(2) . . . no
C(10) C(11) H(112) 109.5(18) . . . no
C(10) C(11) H(113) 109.5(14) . . . no
H(111) C(11) H(112) 109(2) . . . no
H(111) C(11) H(113) 109(3) . . . no
H(112) C(11) H(113) 110(3) . . . no


loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C(10) S(1) C(7) N(1) -179.8(14) . . . . no
C(10) S(1) C(7) C(8) 0.0(15) . . . . no
C(7) S(1) C(10) C(9) -0.1(17) . . . . no
C(7) S(1) C(10) C(11) -179.9(16) . . . . no
C(7) N(1) C(1) C(2) 15(3) . . . . no
C(7) N(1) C(1) C(6) -165.2(19) . . . . no
C(1) N(1) C(7) S(1) 32(2) . . . . no
C(1) N(1) C(7) C(8) -147.4(16) . . . . no
O(1) N(3) C(6) C(1) 158(3) . . . . no
O(1) N(3) C(6) C(5) -21(5) . . . . no
O(2) N(3) C(6) C(1) -22(5) . . . . no
O(2) N(3) C(6) C(5) 159(3) . . . . no
N(1) C(1) C(2) C(3) -180(3) . . . . no
C(6) C(1) C(2) C(3) 0(5) . . . . no
N(1) C(1) C(6) N(3) 0(4) . . . . no
N(1) C(1) C(6) C(5) 180(3) . . . . no
C(2) C(1) C(6) N(3) -180(3) . . . . no
C(2) C(1) C(6) C(5) 0(4) . . . . no
C(1) C(2) C(3) C(4) 0(6) . . . . no
C(2) C(3) C(4) C(5) 0(7) . . . . no
C(3) C(4) C(5) C(6) 0(6) . . . . no
_exptl_crystal_colour            Orange
_exptl_crystal_recrystallization_method 'Used as supplied'
####################################################################### 
# 
# 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_OP_0p152GPa
_database_code_depnum_ccdc_archive 'CCDC 1878577'
_audit_update_record             
;
2018-11-13 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT340_ROY_OP_0p152GPa     
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.01945 Ang.
RESPONSE: Much of the intramolecular geometry was held fixed to known bond distances and angles (CSD: QAXMEH03)- these are not expected to change  significantly over the course of compression. Please see the main manuscript for discussion of intramolecular geometry
;
_vrf_PLAT350_ROY_OP_0p152GPa     
;
PROBLEM: Short C-H (X0.96,N1.08A) C4 - H4 . 0.96 Ang.
RESPONSE: No action taken. A single parameter for C-H bonds was allowed to refine - a search of C-H bonds in the CSD shows this is not abnormally short
;
_vrf_PLAT350_ROY_OP_0p152GPa_2   
;
PROBLEM: Short C-H (X0.96,N1.08A) C9 - H9 . 0.96 Ang.
RESPONSE: No action taken. A single parameter for C-H bonds was allowed to refine - a search of C-H bonds in the CSD shows this is not abnormally short
;
_vrf_PLAT350_ROY_OP_0p152GPa_3   
;
PROBLEM: Short C-H (X0.96,N1.08A) C11 - H111 . 0.96 Ang.
RESPONSE: No action taken. A single parameter for C-H bonds was allowed to refine - a search of C-H bonds in the CSD shows this is not abnormally short
;

_chemical_name_systematic        
;
5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
;
_chemical_name_common            ROY
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 N3 O2 S1'

_chemical_formula_structural     ?
_chemical_formula_sum            'C12 H9 N3 O2 S1'
_chemical_formula_iupac          ?
_chemical_formula_weight         259.28
_chemical_compound_source        'TCI Chemicals'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   7.8566(4)
_cell_length_b                   13.3005(15)
_cell_length_c                   11.6219(10)
_cell_angle_alpha                90
_cell_angle_beta                 104.253(7)
_cell_angle_gamma                90
_cell_volume                     1177.07(18)
_cell_formula_units_Z            4

_cell_measurement_temperature    295
_cell_measurement_pressure       0.152(4) #GPa

_cell_special_details            
;
Cell parameters included in refinement
;

_exptl_crystal_density_diffrn    1.463

_pd_spec_mounting                'TiZr Capsule'
_pd_spec_mount_mode              transmission
_pd_char_colour                  Orange
_chemical_absolute_configuration .

_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
Calculated using MANTID routines.
;

_pd_instr_location               
'ISIS Neutron Facility, Rutherford Appleton Laboratory'
_diffrn_ambient_temperature      295
_diffrn_source                   'Pulsed neutron source'
_diffrn_source_target            W
_diffrn_radiation_type           Neutron
_diffrn_measurement_device_type  'PEARL diffractometer'
_diffrn_radiation_monochromator  none
_diffrn_detector                 'ZnS scintillator'
_diffrn_detector_type            custom

_pd_meas_scan_method             Time-of-flight
_pd_meas_special_details         
;
Time of flight method using a pulsed neutron source
;

# The following three items are used for time-of-flight measurements only.

_pd_instr_dist_src/spec          12800
_pd_instr_dist_spec/detc         800
_pd_meas_2theta_fixed            90

_pd_proc_ls_profile_function     
;
Voigt function convoluted with a back-to-back double exponential.
;

_pd_proc_ls_background_function  'Chebychev polynomial'

_pd_proc_ls_pref_orient_corr     
;
No requirement for preferred orientation correction
;

_pd_proc_ls_prof_R_factor        2.231
_pd_proc_ls_prof_wR_factor       1.800
_pd_proc_ls_prof_R_expected      2.070
_refine_ls_goodness_of_fit_all   0.870
_refine_ls_R_I_factor            1.331

_refine_ls_matrix_type           sparse
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     53
_refine_ls_number_restraints     4
_refine_ls_number_constraints    ?
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_shift/su_max          <0.001

_pd_proc_info_excluded_regions   
;
?

;
_pd_proc_info_data_reduction     
;
Custom ISIS software
;

_refine_special_details          
;The refinement used DFT-optimised structures as a source of restraint on 

torsion angles. A Z-matrix was used, so that distances, angles and 

torsions were refined. Please see the manuscript for a full description 

of refinement details.



Check-cif alerts



PROBLEM: _diffrn_radiation_wavelength is missing

PROBLEM: No Wavelength found in CIF - 0.71073 Ang Assumed     Please Check

RESPONSE: The time of flight method was used





PROBLEM: _atom_site_U_iso_or_equiv is missing

RESPONSE: Topas outputs atomic displacement parameters expressed as 'B' instead

of 'U'. Isotropic B values are given below.





PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01945 Ang.  

PROBLEM: Bond    Calc   1.727(14), Rep     1.72700 ......    Missing s.u.  

PROBLEM: Angle   Calc     92.5(7), Rep       92.50 ......    Missing s.u.  

PROBLEM: Torsion Calc  -179.9(13), Rep     -180.00 ......    Missing s.u.  

(Numerous)



RESPONSE: Much of the intramolecular geometry was held fixed to known

bond distances and angles (CSD: QAXMEH03)- these are not expected to change 

significantly over the course of compression. Please see the main manuscript

for discussion of intramolecular geometry.,The molecular geometry was refined using a constrained and restrained rigid body, using a Z-matrix formalism. Please see main manuscript for full details.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
N1 N 4 -0.0090(19) 0.6720(8) 0.6611(7) 1 1.09(9)
N2 N 4 -0.2345(13) 0.5042(7) 0.4204(7) 1 1.09(9)
N3 N 4 0.084(4) 0.5695(14) 0.8778(7) 1 1.09(9)
O1 O 4 0.161(5) 0.537(2) 0.9757(9) 1 1.09(9)
O2 O 4 0.070(4) 0.5198(13) 0.7866(9) 1 1.09(9)
S1 S 4 0.074(2) 0.8354(7) 0.5392(11) 1 1.09(9)
C1 C 4 -0.036(3) 0.7182(10) 0.7621(9) 1 1.09(9)
C2 C 4 -0.107(4) 0.8138(11) 0.7548(14) 1 1.09(9)
C3 C 4 -0.134(5) 0.8600(14) 0.8558(17) 1 1.09(9)
C4 C 4 -0.089(5) 0.8107(15) 0.9640(15) 1 1.09(9)
C5 C 4 -0.017(4) 0.7151(14) 0.9712(11) 1 1.09(9)
C6 C 4 0.010(3) 0.6689(12) 0.8703(8) 1 1.09(9)
C7 C 4 -0.0133(18) 0.7183(6) 0.5537(8) 1 1.09(9)
C8 C 4 -0.0869(15) 0.6779(6) 0.4453(7) 1 1.09(9)
C9 C 4 -0.0726(18) 0.7420(6) 0.3493(9) 1 1.09(9)
C10 C 4 0.011(2) 0.8300(6) 0.3861(11) 1 1.09(9)
C11 C 4 0.051(3) 0.9150(7) 0.3134(13) 1 1.09(9)
C12 C 4 -0.1690(13) 0.5813(6) 0.4314(7) 1 1.09(9)
H1 H 4 0.022(6) 0.5991(11) 0.6630(13) 1 1.31(11)
H2 H 4 -0.139(4) 0.8482(13) 0.6794(19) 1 1.31(11)
H3 H 4 -0.184(7) 0.9266(19) 0.851(2) 1 1.31(11)
H4 H 4 -0.107(6) 0.8429(17) 1.034(2) 1 1.31(11)
H5 H 4 0.015(5) 0.6807(17) 1.0466(15) 1 1.31(11)
H9 H 4 -0.118(2) 0.7246(7) 0.2668(15) 1 1.31(11)
H111 H 4 0.008(4) 0.9769(11) 0.339(2) 1 1.31(11)
H112 H 4 0.177(3) 0.9199(15) 0.323(2) 1 1.31(11)
H113 H 4 -0.005(4) 0.9034(13) 0.2308(18) 1 1.31(11)


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S(1) C(7) 1.727(14) . . no
S(1) C(10) 1.727(18) . . no
O(1) N(3) 1.23(2) . . no
O(2) N(3) 1.231(18) . . no
N(1) C(1) 1.387(16) . . no
N(1) C(7) 1.385(13) . . no
N(2) C(12) 1.140(13) . . no
N(3) C(6) 1.44(3) . . no
C(1) C(2) 1.38(2) . . no
C(1) C(6) 1.385(16) . . no
C(2) C(3) 1.39(3) . . no
C(3) C(4) 1.39(3) . . no
C(4) C(5) 1.39(3) . . no
C(5) C(6) 1.39(2) . . no
C(7) C(8) 1.360(12) . . no
C(8) C(9) 1.429(13) . . no
C(8) C(12) 1.430(12) . . no
C(9) C(10) 1.359(14) . . no
C(10) C(11) 1.491(17) . . no
N(1) H(1) 1.00(2) . . no
C(2) H(2) 0.97(3) . . no
C(3) H(3) 0.97(4) . . no
C(4) H(4) 0.96(3) . . no
C(5) H(5) 0.97(2) . . no
C(9) H(9) 0.965(19) . . no
C(11) H(111) 0.96(2) . . no
C(11) H(112) 0.97(3) . . no
C(11) H(113) 0.97(3) . . no




loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(7) S(1) C(10) 92.5(7) . . . no
C(1) N(1) C(7) 126.2(10) . . . no
O(1) N(3) O(2) 122(2) . . . no
O(1) N(3) C(6) 118.6(16) . . . no
O(2) N(3) C(6) 119.5(14) . . . no
N(1) C(1) C(2) 119.9(11) . . . no
N(1) C(1) C(6) 119.9(14) . . . no
C(2) C(1) C(6) 120.2(14) . . . no
C(1) C(2) C(3) 119.9(15) . . . no
C(2) C(3) C(4) 120(2) . . . no
C(3) C(4) C(5) 119.9(19) . . . no
C(4) C(5) C(6) 120.1(14) . . . no
N(3) C(6) C(1) 120.1(12) . . . no
N(3) C(6) C(5) 120.0(11) . . . no
C(1) C(6) C(5) 119.9(16) . . . no
S(1) C(7) N(1) 124.6(9) . . . no
S(1) C(7) C(8) 110.7(8) . . . no
N(1) C(7) C(8) 124.7(9) . . . no
C(7) C(8) C(9) 113.0(8) . . . no
C(7) C(8) C(12) 122.4(8) . . . no
C(9) C(8) C(12) 124.6(8) . . . no
C(8) C(9) C(10) 113.1(9) . . . no
S(1) C(10) C(9) 110.7(9) . . . no
S(1) C(10) C(11) 120.4(9) . . . no
C(9) C(10) C(11) 128.9(11) . . . no
N(2) C(12) C(8) 180.0(14) . . . no
C(1) N(1) H(1) 119.9(14) . . . no
C(7) N(1) H(1) 113.8(15) . . . no
C(1) C(2) H(2) 120(2) . . . no
C(3) C(2) H(2) 120(2) . . . no
C(2) C(3) H(3) 120(2) . . . no
C(4) C(3) H(3) 120(3) . . . no
C(3) C(4) H(4) 120(3) . . . no
C(5) C(4) H(4) 120(2) . . . no
C(4) C(5) H(5) 120(2) . . . no
C(6) C(5) H(5) 120(2) . . . no
C(8) C(9) H(9) 123.5(11) . . . no
C(10) C(9) H(9) 123.4(12) . . . no
C(10) C(11) H(111) 110(2) . . . no
C(10) C(11) H(112) 109.7(18) . . . no
C(10) C(11) H(113) 109.6(18) . . . no
H(111) C(11) H(112) 109(3) . . . no
H(111) C(11) H(113) 110(3) . . . no
H(112) C(11) H(113) 109(3) . . . no


loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C(10) S(1) C(7) N(1) -179.9(13) . . . . no
C(10) S(1) C(7) C(8) 0.0(13) . . . . no
C(7) S(1) C(10) C(9) -0.1(14) . . . . no
C(7) S(1) C(10) C(11) -179.9(14) . . . . no
C(7) N(1) C(1) C(2) 14(3) . . . . no
C(7) N(1) C(1) C(6) -165.6(18) . . . . no
C(1) N(1) C(7) S(1) 41(2) . . . . no
C(1) N(1) C(7) C(8) -139.4(17) . . . . no
O(1) N(3) C(6) C(1) 163(3) . . . . no
O(1) N(3) C(6) C(5) -18(4) . . . . no
O(2) N(3) C(6) C(1) -16(4) . . . . no
O(2) N(3) C(6) C(5) 163(3) . . . . no
N(1) C(1) C(2) C(3) 180(3) . . . . no
C(6) C(1) C(2) C(3) -1(4) . . . . no
N(1) C(1) C(6) N(3) -1(3) . . . . no
N(1) C(1) C(6) C(5) -180(2) . . . . no
C(2) C(1) C(6) N(3) -180(2) . . . . no
C(2) C(1) C(6) C(5) 1(4) . . . . no
C(1) C(2) C(3) C(4) 0(5) . . . . no
C(2) C(3) C(4) C(5) 0(5) . . . . no
C(3) C(4) C(5) C(6) 0(5) . . . . no
_exptl_crystal_colour            Orange
_exptl_crystal_recrystallization_method 'Used as supplied'
####################################################################### 
# 
# 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_OP_3p751GPa
_database_code_depnum_ccdc_archive 'CCDC 1878587'
_audit_update_record             
;
2018-11-13 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT413_ROY_OP_3p751GPa     
;
PROBLEM: Short Inter XH3 .. XHn H4 ..H113 . 1.84 Ang. 
RESPONSE: Wood et al (CrystEngComm, 2008, 10, 368-376) have shown that the lower limit for H...H contacts in high-pressure structures is 1.7 A.
;
_vrf_PLAT340_ROY_OP_3p751GPa     
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.01918 Ang. 
RESPONSE: Much of the intramolecular geometry was held fixed to known bond distances and angles (CSD: QAXMEH03)- these are not expected to change  significantly over the course of compression. Please see the main manuscript for discussion of intramolecular geometry
;
_vrf_PLAT430_ROY_OP_3p751GPa     
;
PROBLEM: Short Inter D...A Contact O1 ..O1 . 2.79 Ang. 
RESPONSE: These are high pressure data - short contacts are to be expected
;
_vrf_PLAT430_ROY_OP_3p751GPa_2   
;
PROBLEM: Short Inter D...A Contact O2 ..N2 . 2.79 Ang.
RESPONSE: These are high pressure data - short contacts are to be expected
;

_chemical_name_systematic        
;
5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
;
_chemical_name_common            ROY
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 N3 O2 S1'

_chemical_formula_structural     ?
_chemical_formula_sum            'C12 H9 N3 O2 S1'
_chemical_formula_iupac          ?
_chemical_formula_weight         259.28
_chemical_compound_source        'TCI Chemicals'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   6.8305(5)
_cell_length_b                   12.9782(18)
_cell_length_c                   11.1656(13)
_cell_angle_alpha                90
_cell_angle_beta                 102.712(8)
_cell_angle_gamma                90
_cell_volume                     965.53(19)
_cell_formula_units_Z            4

_cell_measurement_temperature    295
_cell_measurement_pressure       3.751(7) #GPa

_cell_special_details            
;
Cell parameters included in refinement
;

_exptl_crystal_density_diffrn    1.784

_pd_spec_mounting                'TiZr Capsule'
_pd_spec_mount_mode              transmission
_pd_char_colour                  Orange
_chemical_absolute_configuration .

_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
Calculated using MANTID routines.
;

_pd_instr_location               
'ISIS Neutron Facility, Rutherford Appleton Laboratory'
_diffrn_ambient_temperature      295
_diffrn_source                   'Pulsed neutron source'
_diffrn_source_target            W
_diffrn_radiation_type           Neutron
_diffrn_measurement_device_type  'PEARL diffractometer'
_diffrn_radiation_monochromator  none
_diffrn_detector                 'ZnS scintillator'
_diffrn_detector_type            custom

_pd_meas_scan_method             Time-of-flight
_pd_meas_special_details         
;
Time of flight method using a pulsed neutron source
;

# The following three items are used for time-of-flight measurements only.

_pd_instr_dist_src/spec          12800
_pd_instr_dist_spec/detc         800
_pd_meas_2theta_fixed            90

_pd_proc_ls_profile_function     
;
Voigt function convoluted with a back-to-back double exponential.
;

_pd_proc_ls_background_function  'Chebychev polynomial'

_pd_proc_ls_pref_orient_corr     
;
No requirement for preferred orientation correction
;

_pd_proc_ls_prof_R_factor        4.707
_pd_proc_ls_prof_wR_factor       1.670
_pd_proc_ls_prof_R_expected      1.425
_refine_ls_goodness_of_fit_all   1.040
_refine_ls_R_I_factor            1.090

_refine_ls_matrix_type           sparse
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     56
_refine_ls_number_restraints     4
_refine_ls_number_constraints    ?
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_shift/su_max          <0.001

_pd_proc_info_excluded_regions   
;
?

;
_pd_proc_info_data_reduction     
;
Custom ISIS software
;

_refine_special_details          
;The refinement used DFT-optimised structures as a source of restraint on 

torsion angles. A Z-matrix was used, so that distances, angles and 

torsions were refined. Please see the manuscript for a full description 

of refinement details.



Check-cif alerts



PROBLEM: _diffrn_radiation_wavelength is missing

PROBLEM: No Wavelength found in CIF - 0.71073 Ang Assumed     Please Check

RESPONSE: The time of flight method was used





PROBLEM: Short Inter XH3 .. XHn     H4     ..  H113    ..       1.84 Ang.  

PROBLEM: Short Inter D...A Contact  O1     ..  O1      ..       2.79 Ang.  

PROBLEM: Short Inter D...A Contact  O2     ..  N2      ..       2.79 Ang. 

PROBLEM: Short Inter X...Y Contact  S1     ..  C5      ..       3.17 Ang.  

PROBLEM: Short Inter X...Y Contact  S1     ..  C4      ..       3.29 Ang.  

PROBLEM: Short Inter X...Y Contact  O2     ..  C12     ..       2.83 Ang.  

PROBLEM: Short Inter X...Y Contact  N2     ..  C11     ..       2.90 Ang.  

PROBLEM: Short Inter X...Y Contact  N2     ..  C4      ..       3.02 Ang.  

PROBLEM: Short Inter X...Y Contact  C1     ..  C9      ..       3.14 Ang.  

PROBLEM: Short Inter X...Y Contact  C3     ..  C12     ..       3.08 Ang.  

PROBLEM: Short Inter X...Y Contact  C6     ..  C9      ..       3.19 Ang.  

PROBLEM: Short Inter XH3 .. XHn     H4     ..  H113    ..       1.84 Ang.  

RESPONSE: These are high pressure data - short contacts are to be 

expected





PROBLEM: _atom_site_U_iso_or_equiv is missing

RESPONSE: Topas outputs atomic displacement parameters expressed as 'B' instead

of 'U'. Isotropic B values are given below.





PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01918 Ang.  

PROBLEM: Bond    Calc   1.727(14), Rep     1.72700 ......    Missing s.u.  

PROBLEM: Angle   Calc     92.5(7), Rep       92.50 ......    Missing s.u.  

PROBLEM: Torsion Calc  -179.9(13), Rep     -180.00 ......    Missing s.u.  

(Numerous)



RESPONSE: Much of the intramolecular geometry was held fixed to known

bond distances and angles (CSD: QAXMEH03)- these are not expected to change 

significantly over the course of compression. Please see the main manuscript

for discussion of intramolecular geometry.,The molecular geometry was refined using a constrained and restrained rigid body, using a Z-matrix formalism. Please see main manuscript for full details.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
N1 N 4 -0.023(2) 0.6678(7) 0.6575(8) 1 0.58(9)
N2 N 4 -0.2457(17) 0.4909(6) 0.4076(7) 1 0.58(9)
N3 N 4 0.085(5) 0.5591(14) 0.8786(7) 1 0.58(9)
O1 O 4 0.186(6) 0.524(2) 0.9752(10) 1 0.58(9)
O2 O 4 0.044(5) 0.5067(11) 0.7846(10) 1 0.58(9)
S1 S 4 0.068(3) 0.8383(6) 0.5324(11) 1 0.58(9)
C1 C 4 -0.039(3) 0.7160(9) 0.7656(10) 1 0.58(9)
C2 C 4 -0.107(5) 0.8166(11) 0.7632(15) 1 0.58(9)
C3 C 4 -0.123(7) 0.8648(13) 0.8713(18) 1 0.58(9)
C4 C 4 -0.071(7) 0.8125(14) 0.9818(16) 1 0.58(9)
C5 C 4 -0.002(5) 0.7119(14) 0.9842(11) 1 0.58(9)
C6 C 4 0.014(4) 0.6637(12) 0.8761(8) 1 0.58(9)
C7 C 4 -0.023(2) 0.7158(6) 0.5467(8) 1 0.58(9)
C8 C 4 -0.0944(19) 0.6730(5) 0.4343(8) 1 0.58(9)
C9 C 4 -0.076(2) 0.7396(5) 0.3354(9) 1 0.58(9)
C10 C 4 0.009(3) 0.8319(5) 0.3740(10) 1 0.58(9)
C11 C 4 0.053(3) 0.9206(6) 0.2993(13) 1 0.58(9)
C12 C 4 -0.1786(17) 0.5716(6) 0.4195(7) 1 0.58(9)
H1 H 4 0.000(7) 0.5918(9) 0.6564(11) 1 0.69(11)
H2 H 4 -0.146(6) 0.8553(12) 0.682(2) 1 0.69(11)
H3 H 4 -0.174(8) 0.9391(18) 0.870(2) 1 0.69(11)
H4 H 4 -0.082(8) 0.8481(16) 1.062(2) 1 0.69(11)
H5 H 4 0.037(6) 0.6732(17) 1.0659(14) 1 0.69(11)
H9 H 4 -0.122(2) 0.7198(7) 0.2449(15) 1 0.69(11)
H111 H 4 -0.055(5) 0.9757(13) 0.295(3) 1 0.69(11)
H112 H 4 0.190(4) 0.9511(16) 0.339(2) 1 0.69(11)
H113 H 4 0.055(5) 0.8959(9) 0.2126(18) 1 0.69(11)


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S(1) C(7) 1.727(14) . . no
S(1) C(10) 1.727(16) . . no
O(1) N(3) 1.23(3) . . no
O(2) N(3) 1.230(17) . . no
N(1) C(1) 1.385(15) . . no
N(1) C(7) 1.385(13) . . no
N(2) C(12) 1.139(12) . . no
N(3) C(6) 1.44(3) . . no
C(1) C(2) 1.38(2) . . no
C(1) C(6) 1.385(16) . . no
C(2) C(3) 1.39(3) . . no
C(3) C(4) 1.38(3) . . no
C(4) C(5) 1.39(3) . . no
C(5) C(6) 1.39(2) . . no
C(7) C(8) 1.361(12) . . no
C(8) C(9) 1.430(12) . . no
C(8) C(12) 1.431(12) . . no
C(9) C(10) 1.359(13) . . no
C(10) C(11) 1.491(16) . . no
N(1) H(1) 0.999(17) . . no
C(2) H(2) 1.02(3) . . no
C(3) H(3) 1.02(4) . . no
C(4) H(4) 1.03(3) . . no
C(5) H(5) 1.02(2) . . no
C(9) H(9) 1.023(19) . . no
C(11) H(111) 1.02(3) . . no
C(11) H(112) 1.02(3) . . no
C(11) H(113) 1.02(2) . . no


loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(7) S(1) C(10) 92.5(7) . . . no
C(1) N(1) C(7) 126.2(9) . . . no
O(1) N(3) O(2) 121(2) . . . no
O(1) N(3) C(6) 119.1(15) . . . no
O(2) N(3) C(6) 119.5(16) . . . no
N(1) C(1) C(2) 120.0(11) . . . no
N(1) C(1) C(6) 120.0(12) . . . no
C(2) C(1) C(6) 120.0(13) . . . no
C(1) C(2) C(3) 120.0(15) . . . no
C(2) C(3) C(4) 120(2) . . . no
C(3) C(4) C(5) 119.9(19) . . . no
C(4) C(5) C(6) 120.0(14) . . . no
N(3) C(6) C(1) 120.0(11) . . . no
N(3) C(6) C(5) 120.0(11) . . . no
C(1) C(6) C(5) 120.0(16) . . . no
S(1) C(7) N(1) 124.6(8) . . . no
S(1) C(7) C(8) 110.7(8) . . . no
N(1) C(7) C(8) 124.7(8) . . . no
C(7) C(8) C(9) 113.0(7) . . . no
C(7) C(8) C(12) 122.4(8) . . . no
C(9) C(8) C(12) 124.6(8) . . . no
C(8) C(9) C(10) 113.1(9) . . . no
S(1) C(10) C(9) 110.7(8) . . . no
S(1) C(10) C(11) 120.4(9) . . . no
C(9) C(10) C(11) 128.9(10) . . . no
N(2) C(12) C(8) 179.9(15) . . . no
C(1) N(1) H(1) 120.0(13) . . . no
C(7) N(1) H(1) 113.7(13) . . . no
C(1) C(2) H(2) 120(2) . . . no
C(3) C(2) H(2) 120(2) . . . no
C(2) C(3) H(3) 120(2) . . . no
C(4) C(3) H(3) 120(3) . . . no
C(3) C(4) H(4) 120(3) . . . no
C(5) C(4) H(4) 120(2) . . . no
C(4) C(5) H(5) 120(2) . . . no
C(6) C(5) H(5) 120(2) . . . no
C(8) C(9) H(9) 123.5(10) . . . no
C(10) C(9) H(9) 123.5(11) . . . no
C(10) C(11) H(111) 110(2) . . . no
C(10) C(11) H(112) 109.5(17) . . . no
C(10) C(11) H(113) 109.5(11) . . . no
H(111) C(11) H(112) 109(2) . . . no
H(111) C(11) H(113) 110(3) . . . no
H(112) C(11) H(113) 109(3) . . . no


loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C(10) S(1) C(7) N(1) -179.9(13) . . . . no
C(10) S(1) C(7) C(8) 0.1(15) . . . . no
C(7) S(1) C(10) C(9) -0.1(16) . . . . no
C(7) S(1) C(10) C(11) -180.0(16) . . . . no
C(7) N(1) C(1) C(2) 16(3) . . . . no
C(7) N(1) C(1) C(6) -163.4(18) . . . . no
C(1) N(1) C(7) S(1) 31(2) . . . . no
C(1) N(1) C(7) C(8) -149.4(16) . . . . no
O(1) N(3) C(6) C(1) 159(3) . . . . no
O(1) N(3) C(6) C(5) -22(5) . . . . no
O(2) N(3) C(6) C(1) -22(4) . . . . no
O(2) N(3) C(6) C(5) 158(3) . . . . no
N(1) C(1) C(2) C(3) 180(3) . . . . no
C(6) C(1) C(2) C(3) 0(4) . . . . no
N(1) C(1) C(6) N(3) 0(4) . . . . no
N(1) C(1) C(6) C(5) 180(2) . . . . no
C(2) C(1) C(6) N(3) -180(3) . . . . no
C(2) C(1) C(6) C(5) 0(4) . . . . no
C(1) C(2) C(3) C(4) 0(6) . . . . no
C(2) C(3) C(4) C(5) 0(7) . . . . no
C(3) C(4) C(5) C(6) 0(6) . . . . no
_exptl_crystal_colour            Orange
_exptl_crystal_recrystallization_method 'Used as supplied'
####################################################################### 
# 
# 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_OP_5p010GPa
_database_code_depnum_ccdc_archive 'CCDC 1878588'
_audit_update_record             
;
2018-11-13 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT413_ROY_OP_5p010GPa     
;
PROBLEM: Short Inter XH3 .. XHn H4 ..H113 . 1.70 Ang.
RESPONSE: Wood et al (CrystEngComm, 2008, 10, 368-376) have shown that the lower limit for H...H contacts in high-pressure structures is 1.7 A.
;
_vrf_PLAT340_ROY_OP_5p010GPa     
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.01927 Ang. 
RESPONSE: Much of the intramolecular geometry was held fixed to known bond distances and angles (CSD: QAXMEH03)- these are not expected to change  significantly over the course of compression. Please see the main manuscript for discussion of intramolecular geometry
;
_vrf_PLAT430_ROY_OP_5p010GPa     
;
PROBLEM: Short Inter D...A Contact O1 ..O1 . 2.76 Ang. 
RESPONSE: These are high pressure data - short contacts are to be expected
;
_vrf_PLAT430_ROY_OP_5p010GPa_2   
;
PROBLEM: Short Inter D...A Contact O2 ..N2 . 2.78 Ang.
RESPONSE: These are high pressure data - short contacts are to be expected
;
_vrf_PLAT430_ROY_OP_5p010GPa_3   
;
PROBLEM: Short Inter D...A Contact O1 ..N3 . 2.89 Ang.
RESPONSE: These are high pressure data - short contacts are to be expected
;
_vrf_PLAT411_ROY_OP_5p010GPa     
;
PROBLEM: Short Inter H...H Contact H2 ..H5 . 2.14 Ang. 
RESPONSE: These are high pressure data - short contacts are to be expected
;

_chemical_name_systematic        
;
5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
;
_chemical_name_common            ROY
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 N3 O2 S1'

_chemical_formula_structural     ?
_chemical_formula_sum            'C12 H9 N3 O2 S1'
_chemical_formula_iupac          ?
_chemical_formula_weight         259.28
_chemical_compound_source        'TCI Chemicals'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   6.6919(5)
_cell_length_b                   12.9085(17)
_cell_length_c                   11.0915(13)
_cell_angle_alpha                90
_cell_angle_beta                 102.807(9)
_cell_angle_gamma                90
_cell_volume                     934.27(18)
_cell_formula_units_Z            4

_cell_measurement_temperature    295
_cell_measurement_pressure       5.010(8) #GPa

_cell_special_details            
;
Cell parameters included in refinement
;

_exptl_crystal_density_diffrn    1.843

_pd_spec_mounting                'TiZr Capsule'
_pd_spec_mount_mode              transmission
_pd_char_colour                  Orange
_chemical_absolute_configuration .

_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
Calculated using MANTID routines.
;

_pd_instr_location               
'ISIS Neutron Facility, Rutherford Appleton Laboratory'
_diffrn_ambient_temperature      295
_diffrn_source                   'Pulsed neutron source'
_diffrn_source_target            W
_diffrn_radiation_type           Neutron
_diffrn_measurement_device_type  'PEARL diffractometer'
_diffrn_radiation_monochromator  none
_diffrn_detector                 'ZnS scintillator'
_diffrn_detector_type            custom

_pd_meas_scan_method             Time-of-flight
_pd_meas_special_details         
;
Time of flight method using a pulsed neutron source
;

# The following three items are used for time-of-flight measurements only.

_pd_instr_dist_src/spec          12800
_pd_instr_dist_spec/detc         800
_pd_meas_2theta_fixed            90

_pd_proc_ls_profile_function     
;
Voigt function convoluted with a back-to-back double exponential.
;

_pd_proc_ls_background_function  'Chebychev polynomial'

_pd_proc_ls_pref_orient_corr     
;
No requirement for preferred orientation correction
;

_pd_proc_ls_prof_R_factor        5.505
_pd_proc_ls_prof_wR_factor       1.794
_pd_proc_ls_prof_R_expected      1.754
_refine_ls_goodness_of_fit_all   0.925
_refine_ls_R_I_factor            0.968

_refine_ls_matrix_type           sparse
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     56
_refine_ls_number_restraints     4
_refine_ls_number_constraints    ?
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_shift/su_max          <0.001

_pd_proc_info_excluded_regions   
;
?

;
_pd_proc_info_data_reduction     
;
Custom ISIS software
;

_refine_special_details          
;The refinement used DFT-optimised structures as a source of restraint on 

torsion angles. A Z-matrix was used, so that distances, angles and 

torsions were refined. Please see the manuscript for a full description 

of refinement details.



Check-cif alerts



PROBLEM: _diffrn_radiation_wavelength is missing

PROBLEM: No Wavelength found in CIF - 0.71073 Ang Assumed     Please Check

RESPONSE: The time of flight method was used





PROBLEM: Short Inter XH3 .. XHn     H4     ..  H113    ..       1.70 Ang.

PROBLEM: Short Inter D...A Contact  O1     ..  O1      ..       2.76 Ang.  

PROBLEM: Short Inter D...A Contact  O2     ..  N2      ..       2.78 Ang.  

PROBLEM: Short Inter H...H Contact   H2     ..  H5      .       2.14 Ang.  

PROBLEM: Short Inter D...A Contact  O1     ..  N3      ..       2.89 Ang.  

PROBLEM: Short Inter X...Y Contact  S1     ..  C5      ..       3.16 Ang.  

PROBLEM: Short Inter X...Y Contact  O2     ..  C12     ..       2.82 Ang.  

PROBLEM: Short Inter X...Y Contact  N2     ..  C11     ..       2.78 Ang.  

PROBLEM: Short Inter X...Y Contact  N2     ..  C4      ..       2.94 Ang.  

PROBLEM: Short Inter X...Y Contact  C1     ..  C9      ..       3.06 Ang.  

PROBLEM: Short Inter X...Y Contact  C3     ..  C12     ..       3.02 Ang.  

PROBLEM: Short Inter X...Y Contact  C6     ..  C9      ..       3.12 Ang.  

RESPONSE: These are high pressure data - short contacts are to be 

expected





PROBLEM: _atom_site_U_iso_or_equiv is missing

RESPONSE: Topas outputs atomic displacement parameters expressed as 'B' instead

of 'U'. Isotropic B values are given below.





PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01927 Ang.  

PROBLEM: Bond    Calc   1.728(14), Rep     1.72800 ......    Missing s.u.  

PROBLEM: Angle   Calc     92.5(7), Rep       92.50 ......    Missing s.u.  

PROBLEM: Torsion Calc  -179.9(13), Rep     -180.00 ......    Missing s.u.  

(Numerous)



RESPONSE: Much of the intramolecular geometry was held fixed to known

bond distances and angles (CSD: QAXMEH03)- these are not expected to change 

significantly over the course of compression. Please see the main manuscript

for discussion of intramolecular geometry.,The molecular geometry was refined using a constrained and restrained rigid body, using a Z-matrix formalism. Please see main manuscript for full details.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
N1 N 4 -0.030(2) 0.6689(8) 0.6576(8) 1 0.33(9)
N2 N 4 -0.2478(16) 0.4891(6) 0.4059(8) 1 0.33(9)
N3 N 4 0.085(5) 0.5599(14) 0.8802(8) 1 0.33(9)
O1 O 4 0.189(7) 0.525(2) 0.9772(10) 1 0.33(9)
O2 O 4 0.042(6) 0.5073(12) 0.7856(10) 1 0.33(9)
S1 S 4 0.059(3) 0.8412(6) 0.5316(11) 1 0.33(9)
C1 C 4 -0.044(4) 0.7175(10) 0.7667(10) 1 0.33(9)
C2 C 4 -0.114(5) 0.8186(11) 0.7646(15) 1 0.33(9)
C3 C 4 -0.128(7) 0.8671(13) 0.8737(18) 1 0.33(9)
C4 C 4 -0.072(7) 0.8146(14) 0.9850(16) 1 0.33(9)
C5 C 4 -0.002(6) 0.7135(14) 0.9872(11) 1 0.33(9)
C6 C 4 0.012(4) 0.6650(12) 0.8780(8) 1 0.33(9)
C7 C 4 -0.030(2) 0.7172(6) 0.5461(9) 1 0.33(9)
C8 C 4 -0.0999(18) 0.6735(5) 0.4329(8) 1 0.33(9)
C9 C 4 -0.082(2) 0.7406(6) 0.3333(9) 1 0.33(9)
C10 C 4 0.001(3) 0.8342(6) 0.3722(11) 1 0.33(9)
C11 C 4 0.044(3) 0.9238(6) 0.2970(13) 1 0.33(9)
C12 C 4 -0.1822(16) 0.5709(6) 0.4178(7) 1 0.33(9)
H1 H 4 -0.006(7) 0.5925(9) 0.6564(12) 1 0.39(11)
H2 H 4 -0.157(6) 0.8589(13) 0.679(2) 1 0.39(11)
H3 H 4 -0.182(9) 0.9448(18) 0.872(2) 1 0.39(11)
H4 H 4 -0.083(8) 0.8519(17) 1.069(2) 1 0.39(11)
H5 H 4 0.041(7) 0.6732(18) 1.0727(15) 1 0.39(11)
H9 H 4 -0.129(2) 0.7195(7) 0.2384(15) 1 0.39(11)
H111 H 4 -0.075(4) 0.9795(13) 0.290(3) 1 0.39(11)
H112 H 4 0.187(4) 0.9582(15) 0.3406(19) 1 0.39(11)
H113 H 4 0.052(5) 0.8976(9) 0.2071(18) 1 0.39(11)


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S(1) C(7) 1.728(14) . . no
S(1) C(10) 1.726(17) . . no
O(1) N(3) 1.23(3) . . no
O(2) N(3) 1.229(18) . . no
N(1) C(1) 1.385(16) . . no
N(1) C(7) 1.385(13) . . no
N(2) C(12) 1.140(12) . . no
N(3) C(6) 1.44(3) . . no
C(1) C(2) 1.39(2) . . no
C(1) C(6) 1.385(16) . . no
C(2) C(3) 1.38(3) . . no
C(3) C(4) 1.39(3) . . no
C(4) C(5) 1.39(3) . . no
C(5) C(6) 1.39(2) . . no
C(7) C(8) 1.361(13) . . no
C(8) C(9) 1.430(12) . . no
C(8) C(12) 1.430(11) . . no
C(9) C(10) 1.360(14) . . no
C(10) C(11) 1.491(16) . . no
N(1) H(1) 1.000(18) . . no
C(2) H(2) 1.07(3) . . no
C(3) H(3) 1.07(4) . . no
C(4) H(4) 1.07(3) . . no
C(5) H(5) 1.06(2) . . no
C(9) H(9) 1.065(19) . . no
C(11) H(111) 1.06(3) . . no
C(11) H(112) 1.07(3) . . no
C(11) H(113) 1.07(2) . . no


loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(7) S(1) C(10) 92.5(7) . . . no
C(1) N(1) C(7) 126.2(10) . . . no
O(1) N(3) O(2) 122(2) . . . no
O(1) N(3) C(6) 118.9(15) . . . no
O(2) N(3) C(6) 119.4(17) . . . no
N(1) C(1) C(2) 120.0(12) . . . no
N(1) C(1) C(6) 120.0(13) . . . no
C(2) C(1) C(6) 120.0(13) . . . no
C(1) C(2) C(3) 120.0(15) . . . no
C(2) C(3) C(4) 120.0(19) . . . no
C(3) C(4) C(5) 120.0(18) . . . no
C(4) C(5) C(6) 119.9(14) . . . no
N(3) C(6) C(1) 120.0(11) . . . no
N(3) C(6) C(5) 120.0(12) . . . no
C(1) C(6) C(5) 120.1(16) . . . no
S(1) C(7) N(1) 124.6(8) . . . no
S(1) C(7) C(8) 110.7(8) . . . no
N(1) C(7) C(8) 124.7(8) . . . no
C(7) C(8) C(9) 113.0(7) . . . no
C(7) C(8) C(12) 122.5(8) . . . no
C(9) C(8) C(12) 124.5(8) . . . no
C(8) C(9) C(10) 113.1(9) . . . no
S(1) C(10) C(9) 110.8(9) . . . no
S(1) C(10) C(11) 120.3(9) . . . no
C(9) C(10) C(11) 128.9(11) . . . no
N(2) C(12) C(8) 179.9(15) . . . no
C(1) N(1) H(1) 120.1(13) . . . no
C(7) N(1) H(1) 113.6(14) . . . no
C(1) C(2) H(2) 119.9(19) . . . no
C(3) C(2) H(2) 120(2) . . . no
C(2) C(3) H(3) 120(2) . . . no
C(4) C(3) H(3) 120(2) . . . no
C(3) C(4) H(4) 120(3) . . . no
C(5) C(4) H(4) 120(2) . . . no
C(4) C(5) H(5) 120(2) . . . no
C(6) C(5) H(5) 120(2) . . . no
C(8) C(9) H(9) 123.5(10) . . . no
C(10) C(9) H(9) 123.5(11) . . . no
C(10) C(11) H(111) 109(2) . . . no
C(10) C(11) H(112) 109.5(16) . . . no
C(10) C(11) H(113) 109.5(11) . . . no
H(111) C(11) H(112) 109.5(19) . . . no
H(111) C(11) H(113) 110(3) . . . no
H(112) C(11) H(113) 109(3) . . . no


loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C(10) S(1) C(7) N(1) -179.9(13) . . . . no
C(10) S(1) C(7) C(8) 0.2(14) . . . . no
C(7) S(1) C(10) C(9) -0.2(16) . . . . no
C(7) S(1) C(10) C(11) -180.0(16) . . . . no
C(7) N(1) C(1) C(2) 17(3) . . . . no
C(7) N(1) C(1) C(6) -162.7(19) . . . . no
C(1) N(1) C(7) S(1) 29(2) . . . . no
C(1) N(1) C(7) C(8) -151.3(18) . . . . no
O(1) N(3) C(6) C(1) 159(3) . . . . no
O(1) N(3) C(6) C(5) -21(5) . . . . no
O(2) N(3) C(6) C(1) -22(5) . . . . no
O(2) N(3) C(6) C(5) 159(3) . . . . no
N(1) C(1) C(2) C(3) 180(3) . . . . no
C(6) C(1) C(2) C(3) 0(5) . . . . no
N(1) C(1) C(6) N(3) 0(4) . . . . no
N(1) C(1) C(6) C(5) -180(3) . . . . no
C(2) C(1) C(6) N(3) -180(3) . . . . no
C(2) C(1) C(6) C(5) 0(4) . . . . no
C(1) C(2) C(3) C(4) 0(6) . . . . no
C(2) C(3) C(4) C(5) 0(7) . . . . no
C(3) C(4) C(5) C(6) 0(6) . . . . no
_exptl_crystal_colour            Orange
_exptl_crystal_recrystallization_method 'Used as supplied'
####################################################################### 
# 
# 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_OP_3p186GPa
_database_code_depnum_ccdc_archive 'CCDC 1878586'
_audit_update_record             
;
2018-11-13 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT413_ROY_OP_3p186GPa     
;
PROBLEM: Short Inter XH3 .. XHn H4 ..H113 . 1.82 Ang.
RESPONSE: Wood et al (CrystEngComm, 2008, 10, 368-376) have shown that the lower limit for H...H contacts in high-pressure structures is 1.7 A.
;
_vrf_PLAT340_ROY_OP_3p186GPa     
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.02064 Ang. 
RESPONSE: Much of the intramolecular geometry was held fixed to known bond distances and angles (CSD: QAXMEH03)- these are not expected to change  significantly over the course of compression. Please see the main manuscript for discussion of intramolecular geometry
;
_vrf_PLAT430_ROY_OP_3p186GPa     
;
PROBLEM: Short Inter D...A Contact O1 ..O1 . 2.76 Ang. 
RESPONSE: These are high pressure data - short contacts are to be expected
;
_vrf_PLAT430_ROY_OP_3p186GPa_2   
;
PROBLEM: Short Inter D...A Contact O2 ..N2 . 2.76 Ang.
RESPONSE: These are high pressure data - short contacts are to be expected
;

_chemical_name_systematic        
;
5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
;
_chemical_name_common            ROY
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 N3 O2 S1'

_chemical_formula_structural     ?
_chemical_formula_sum            'C12 H9 N3 O2 S1'
_chemical_formula_iupac          ?
_chemical_formula_weight         259.28
_chemical_compound_source        'TCI Chemicals'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   6.9097(5)
_cell_length_b                   13.022(2)
_cell_length_c                   11.1993(15)
_cell_angle_alpha                90
_cell_angle_beta                 102.719(8)
_cell_angle_gamma                90
_cell_volume                     983.0(2)
_cell_formula_units_Z            4

_cell_measurement_temperature    295
_cell_measurement_pressure       3.186(7) #GPa

_cell_special_details            
;
Cell parameters included in refinement
;

_exptl_crystal_density_diffrn    1.752

_pd_spec_mounting                'TiZr Capsule'
_pd_spec_mount_mode              transmission
_pd_char_colour                  Orange
_chemical_absolute_configuration .

_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
Calculated using MANTID routines.
;

_pd_instr_location               
'ISIS Neutron Facility, Rutherford Appleton Laboratory'
_diffrn_ambient_temperature      295
_diffrn_source                   'Pulsed neutron source'
_diffrn_source_target            W
_diffrn_radiation_type           Neutron
_diffrn_measurement_device_type  'PEARL diffractometer'
_diffrn_radiation_monochromator  none
_diffrn_detector                 'ZnS scintillator'
_diffrn_detector_type            custom

_pd_meas_scan_method             Time-of-flight
_pd_meas_special_details         
;
Time of flight method using a pulsed neutron source
;

# The following three items are used for time-of-flight measurements only.

_pd_instr_dist_src/spec          12800
_pd_instr_dist_spec/detc         800
_pd_meas_2theta_fixed            90

_pd_proc_ls_profile_function     
;
Voigt function convoluted with a back-to-back double exponential.
;

_pd_proc_ls_background_function  'Chebychev polynomial'

_pd_proc_ls_pref_orient_corr     
;
No requirement for preferred orientation correction
;

_pd_proc_ls_prof_R_factor        6.583
_pd_proc_ls_prof_wR_factor       1.955
_pd_proc_ls_prof_R_expected      2.017
_refine_ls_goodness_of_fit_all   0.858
_refine_ls_R_I_factor            1.132

_refine_ls_matrix_type           sparse
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     56
_refine_ls_number_restraints     4
_refine_ls_number_constraints    ?
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_shift/su_max          <0.001

_pd_proc_info_excluded_regions   
;
?

;
_pd_proc_info_data_reduction     
;
Custom ISIS software
;

_refine_special_details          
;The refinement used DFT-optimised structures as a source of restraint on 

torsion angles. A Z-matrix was used, so that distances, angles and 

torsions were refined. Please see the manuscript for a full description 

of refinement details.



Check-cif alerts



PROBLEM: _diffrn_radiation_wavelength is missing

PROBLEM: No Wavelength found in CIF - 0.71073 Ang Assumed     Please Check

RESPONSE: The time of flight method was used





PROBLEM: Short Inter D...A Contact  O1     ..  O1      ..       2.76 Ang.  

PROBLEM: Short Inter D...A Contact  O2     ..  N2      ..       2.76 Ang.  

PROBLEM: Short Inter X...Y Contact  S1     ..  C5      ..       3.18 Ang. 

PROBLEM: Short Inter X...Y Contact  S1     ..  C4      ..       3.30 Ang.  

PROBLEM: Short Inter X...Y Contact  O2     ..  C12     ..       2.82 Ang.  

PROBLEM: Short Inter X...Y Contact  N2     ..  C11     ..       2.97 Ang.  

PROBLEM: Short Inter X...Y Contact  N2     ..  C4      ..       3.05 Ang.  

PROBLEM: Short Inter X...Y Contact  C1     ..  C9      ..       3.20 Ang.  

PROBLEM: Short Inter X...Y Contact  C3     ..  C12     ..       3.19 Ang.   

PROBLEM: Short Inter XH3 .. XHn     H4     ..  H113    ..       1.82 Ang.  

RESPONSE: These are high pressure data - short contacts are to be 

expected





PROBLEM: _atom_site_U_iso_or_equiv is missing

RESPONSE: Topas outputs atomic displacement parameters expressed as 'B' instead

of 'U'. Isotropic B values are given below.





PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02064 Ang.  

PROBLEM: Bond    Calc   1.726(14), Rep     1.72600 ......    Missing s.u.  

PROBLEM: Angle   Calc     92.6(7), Rep       92.60 ......    Missing s.u.  

PROBLEM: Torsion Calc    -0.1(15), Rep        0.00 ......    Missing s.u.  

(Numerous)



RESPONSE: Much of the intramolecular geometry was held fixed to known

bond distances and angles (CSD: QAXMEH03)- these are not expected to change 

significantly over the course of compression. Please see the main manuscript

for discussion of intramolecular geometry.,The molecular geometry was refined using a constrained and restrained rigid body, using a Z-matrix formalism. Please see main manuscript for full details.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
N1 N 4 -0.020(3) 0.6689(8) 0.6572(8) 1 0.41(10)
N2 N 4 -0.2369(17) 0.4911(7) 0.4089(8) 1 0.41(10)
N3 N 4 0.084(5) 0.5616(15) 0.8785(8) 1 0.41(10)
O1 O 4 0.181(7) 0.527(2) 0.9761(10) 1 0.41(10)
O2 O 4 0.049(6) 0.5095(13) 0.7846(10) 1 0.41(10)
S1 S 4 0.068(3) 0.8387(6) 0.5315(12) 1 0.41(10)
C1 C 4 -0.039(4) 0.7171(10) 0.7641(11) 1 0.41(10)
C2 C 4 -0.110(6) 0.8169(12) 0.7605(16) 1 0.41(10)
C3 C 4 -0.129(7) 0.8650(14) 0.867(2) 1 0.41(10)
C4 C 4 -0.079(7) 0.8134(15) 0.9781(17) 1 0.41(10)
C5 C 4 -0.008(6) 0.7136(15) 0.9817(12) 1 0.41(10)
C6 C 4 0.011(4) 0.6654(13) 0.8748(9) 1 0.41(10)
C7 C 4 -0.020(2) 0.7164(6) 0.5465(9) 1 0.41(10)
C8 C 4 -0.090(2) 0.6731(6) 0.4347(8) 1 0.41(10)
C9 C 4 -0.072(2) 0.7393(6) 0.3357(9) 1 0.41(10)
C10 C 4 0.011(3) 0.8317(6) 0.3737(11) 1 0.41(10)
C11 C 4 0.053(4) 0.9200(7) 0.2988(14) 1 0.41(10)
C12 C 4 -0.1717(17) 0.5718(6) 0.4203(7) 1 0.41(10)
H1 H 4 0.004(7) 0.5932(10) 0.6566(12) 1 0.49(12)
H2 H 4 -0.148(6) 0.8559(14) 0.677(2) 1 0.49(12)
H3 H 4 -0.182(9) 0.941(2) 0.865(2) 1 0.49(12)
H4 H 4 -0.093(9) 0.8498(18) 1.059(2) 1 0.49(12)
H5 H 4 0.030(7) 0.6745(19) 1.0654(16) 1 0.49(12)
H9 H 4 -0.118(3) 0.7187(8) 0.2434(16) 1 0.49(12)
H111 H 4 -0.049(5) 0.9790(14) 0.301(3) 1 0.49(12)
H112 H 4 0.197(5) 0.9469(18) 0.334(2) 1 0.49(12)
H113 H 4 0.041(6) 0.8961(11) 0.208(2) 1 0.49(12)


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S(1) C(7) 1.726(14) . . no
S(1) C(10) 1.726(18) . . no
O(1) N(3) 1.24(3) . . no
O(2) N(3) 1.230(18) . . no
N(1) C(1) 1.383(18) . . no
N(1) C(7) 1.386(14) . . no
N(2) C(12) 1.139(13) . . no
N(3) C(6) 1.44(3) . . no
C(1) C(2) 1.39(3) . . no
C(1) C(6) 1.386(17) . . no
C(2) C(3) 1.38(3) . . no
C(3) C(4) 1.39(3) . . no
C(4) C(5) 1.39(3) . . no
C(5) C(6) 1.38(2) . . no
C(7) C(8) 1.361(13) . . no
C(8) C(9) 1.431(13) . . no
C(8) C(12) 1.430(12) . . no
C(9) C(10) 1.360(14) . . no
C(10) C(11) 1.489(18) . . no
N(1) H(1) 1.000(19) . . no
C(2) H(2) 1.05(3) . . no
C(3) H(3) 1.05(4) . . no
C(4) H(4) 1.05(4) . . no
C(5) H(5) 1.05(2) . . no
C(9) H(9) 1.05(2) . . no
C(11) H(111) 1.05(3) . . no
C(11) H(112) 1.05(4) . . no
C(11) H(113) 1.05(3) . . no


loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(7) S(1) C(10) 92.6(7) . . . no
C(1) N(1) C(7) 126.2(10) . . . no
O(1) N(3) O(2) 122(2) . . . no
O(1) N(3) C(6) 119.1(16) . . . no
O(2) N(3) C(6) 119.4(17) . . . no
N(1) C(1) C(2) 120.0(12) . . . no
N(1) C(1) C(6) 120.1(14) . . . no
C(2) C(1) C(6) 119.9(15) . . . no
C(1) C(2) C(3) 120.1(16) . . . no
C(2) C(3) C(4) 120(2) . . . no
C(3) C(4) C(5) 120(2) . . . no
C(4) C(5) C(6) 120.0(15) . . . no
N(3) C(6) C(1) 119.9(12) . . . no
N(3) C(6) C(5) 120.0(12) . . . no
C(1) C(6) C(5) 120.1(17) . . . no
S(1) C(7) N(1) 124.6(9) . . . no
S(1) C(7) C(8) 110.7(8) . . . no
N(1) C(7) C(8) 124.6(9) . . . no
C(7) C(8) C(9) 112.9(8) . . . no
C(7) C(8) C(12) 122.5(8) . . . no
C(9) C(8) C(12) 124.6(8) . . . no
C(8) C(9) C(10) 113.1(9) . . . no
S(1) C(10) C(9) 110.6(9) . . . no
S(1) C(10) C(11) 120.5(9) . . . no
C(9) C(10) C(11) 128.9(11) . . . no
N(2) C(12) C(8) 179.9(16) . . . no
C(1) N(1) H(1) 120.0(14) . . . no
C(7) N(1) H(1) 113.7(15) . . . no
C(1) C(2) H(2) 120(2) . . . no
C(3) C(2) H(2) 120(2) . . . no
C(2) C(3) H(3) 121(2) . . . no
C(4) C(3) H(3) 119(3) . . . no
C(3) C(4) H(4) 120(3) . . . no
C(5) C(4) H(4) 120(2) . . . no
C(4) C(5) H(5) 120(2) . . . no
C(6) C(5) H(5) 120(3) . . . no
C(8) C(9) H(9) 123.4(11) . . . no
C(10) C(9) H(9) 123.4(12) . . . no
C(10) C(11) H(111) 110(3) . . . no
C(10) C(11) H(112) 109.5(19) . . . no
C(10) C(11) H(113) 109.5(14) . . . no
H(111) C(11) H(112) 110(2) . . . no
H(111) C(11) H(113) 109(3) . . . no
H(112) C(11) H(113) 109(3) . . . no



loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C(10) S(1) C(7) N(1) -180.0(15) . . . . no
C(10) S(1) C(7) C(8) -0.1(15) . . . . no
C(7) S(1) C(10) C(9) 0.1(17) . . . . no
C(7) S(1) C(10) C(11) 179.8(18) . . . . no
C(7) N(1) C(1) C(2) 16(4) . . . . no
C(7) N(1) C(1) C(6) -164(2) . . . . no
C(1) N(1) C(7) S(1) 31(3) . . . . no
C(1) N(1) C(7) C(8) -149(2) . . . . no
O(1) N(3) C(6) C(1) 159(3) . . . . no
O(1) N(3) C(6) C(5) -21(5) . . . . no
O(2) N(3) C(6) C(1) -21(5) . . . . no
O(2) N(3) C(6) C(5) 160(4) . . . . no
N(1) C(1) C(2) C(3) 180(3) . . . . no
C(6) C(1) C(2) C(3) 1(5) . . . . no
N(1) C(1) C(6) N(3) 0(4) . . . . no
N(1) C(1) C(6) C(5) -180(3) . . . . no
C(2) C(1) C(6) N(3) 180(3) . . . . no
C(2) C(1) C(6) C(5) -1(4) . . . . no
C(1) C(2) C(3) C(4) -1(6) . . . . no
C(2) C(3) C(4) C(5) 1(7) . . . . no
C(3) C(4) C(5) C(6) -1(6) . . . . no
_exptl_crystal_colour            Orange
_exptl_crystal_recrystallization_method 'Used as supplied'
####################################################################### 
# 
# 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_OP_5p842GPa
_database_code_depnum_ccdc_archive 'CCDC 1878589'
_audit_update_record             
;
2018-11-13 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT413_ROY_OP_5p842GPa     
;
PROBLEM: Short Inter XH3 .. XHn H4 ..H113 . 1.71 Ang.
RESPONSE: Wood et al (CrystEngComm, 2008, 10, 368-376) have shown that the lower limit for H...H contacts in high-pressure structures is 1.7 A.
;
_vrf_PLAT340_ROY_OP_5p842GPa     
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.01736 Ang. 
RESPONSE: Much of the intramolecular geometry was held fixed to known bond distances and angles (CSD: QAXMEH03)- these are not expected to change  significantly over the course of compression. Please see the main manuscript for discussion of intramolecular geometry
;
_vrf_PLAT430_ROY_OP_5p842GPa     
;
PROBLEM: Short Inter D...A Contact S1 ..O1 . 2.87 Ang. 
RESPONSE: These are high pressure data - short contacts are to be expected
;
_vrf_PLAT430_ROY_OP_5p842GPa_2   
;
PROBLEM: Short Inter D...A Contact O1 ..O1 . 2.80 Ang. 
RESPONSE: These are high pressure data - short contacts are to be expected
;
_vrf_PLAT430_ROY_OP_5p842GPa_3   
;
PROBLEM: Short Inter D...A Contact O2 ..N2 . 2.71 Ang. 
RESPONSE: These are high pressure data - short contacts are to be expected
;
_vrf_PLAT430_ROY_OP_5p842GPa_4   
;
PROBLEM: Short Inter D...A Contact O1 ..N3 . 2.89 Ang.
RESPONSE: These are high pressure data - short contacts are to be expected
;
_vrf_PLAT411_ROY_OP_5p842GPa     
;
PROBLEM: Short Inter H...H Contact H2 ..H5 . 2.06 Ang. 
RESPONSE: These are high pressure data - short contacts are to be expected
;

_chemical_name_systematic        
;
5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
;
_chemical_name_common            ROY
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H9 N3 O2 S1'

_chemical_formula_structural     ?
_chemical_formula_sum            'C12 H9 N3 O2 S1'
_chemical_formula_iupac          ?
_chemical_formula_weight         259.28
_chemical_compound_source        'TCI Chemicals'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   6.6153(5)
_cell_length_b                   12.8677(16)
_cell_length_c                   11.0478(12)
_cell_angle_alpha                90
_cell_angle_beta                 102.898(8)
_cell_angle_gamma                90
_cell_volume                     916.70(17)
_cell_formula_units_Z            4

_cell_measurement_temperature    295
_cell_measurement_pressure       5.842(8) #GPa

_cell_special_details            
;
Cell parameters included in refinement
;

_exptl_crystal_density_diffrn    1.879

_pd_spec_mounting                'TiZr Capsule'
_pd_spec_mount_mode              transmission
_pd_char_colour                  Orange
_chemical_absolute_configuration .

_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
Calculated using MANTID routines.
;

_pd_instr_location               
'ISIS Neutron Facility, Rutherford Appleton Laboratory'
_diffrn_ambient_temperature      295
_diffrn_source                   'Pulsed neutron source'
_diffrn_source_target            W
_diffrn_radiation_type           Neutron
_diffrn_measurement_device_type  'PEARL diffractometer'
_diffrn_radiation_monochromator  none
_diffrn_detector                 'ZnS scintillator'
_diffrn_detector_type            custom

_pd_meas_scan_method             Time-of-flight
_pd_meas_special_details         
;
Time of flight method using a pulsed neutron source
;

# The following three items are used for time-of-flight measurements only.

_pd_instr_dist_src/spec          12800
_pd_instr_dist_spec/detc         800
_pd_meas_2theta_fixed            90

_pd_proc_ls_profile_function     
;
Voigt function convoluted with a back-to-back double exponential.
;

_pd_proc_ls_background_function  'Chebychev polynomial'

_pd_proc_ls_pref_orient_corr     
;
No requirement for preferred orientation correction
;

_pd_proc_ls_prof_R_factor        5.092
_pd_proc_ls_prof_wR_factor       1.751
_pd_proc_ls_prof_R_expected      1.525
_refine_ls_goodness_of_fit_all   1.002
_refine_ls_R_I_factor            1.105

_refine_ls_matrix_type           sparse
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     57
_refine_ls_number_restraints     4
_refine_ls_number_constraints    ?
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_shift/su_max          <0.001

_pd_proc_info_excluded_regions   
;
?

;
_pd_proc_info_data_reduction     
;
Custom ISIS software
;

_refine_special_details          
;The refinement used DFT-optimised structures as a source of restraint on 

torsion angles. A Z-matrix was used, so that distances, angles and 

torsions were refined. Please see the manuscript for a full description 

of refinement details.



Check-cif alerts



PROBLEM: _diffrn_radiation_wavelength is missing

PROBLEM: No Wavelength found in CIF - 0.71073 Ang Assumed     Please Check

RESPONSE: The time of flight method was used





PROBLEM: Short Inter XH3 .. XHn     H4     ..  H113    ..       1.71 Ang.  

PROBLEM: Short Inter D...A Contact  S1     ..  O1      ..       2.87 Ang.  

PROBLEM: Short Inter D...A Contact  O1     ..  O1      ..       2.80 Ang.  

PROBLEM: Short Inter D...A Contact  O2     ..  N2      ..       2.71 Ang.  

PROBLEM: Short Inter H...H Contact   H2     ..  H5      .       2.06 Ang.  

PROBLEM: Short Inter D...A Contact  O1     ..  N3      ..       2.89 Ang.  

PROBLEM: Short Inter X...Y Contact  S1     ..  C5      ..       3.15 Ang.  

PROBLEM: Short Inter X...Y Contact  S1     ..  C4      ..       3.27 Ang.  

PROBLEM: Short Inter X...Y Contact  O1     ..  C11     ..       2.98 Ang.  

PROBLEM: Short Inter X...Y Contact  O2     ..  C12     ..       2.75 Ang.  

PROBLEM: Short Inter X...Y Contact  N2     ..  C11     ..       2.72 Ang.  

PROBLEM: Short Inter X...Y Contact  N2     ..  C4      ..       2.94 Ang.  

PROBLEM: Short Inter X...Y Contact  C1     ..  C9      ..       3.03 Ang.  

PROBLEM: Short Inter X...Y Contact  C3     ..  C12     ..       3.03 Ang.  

PROBLEM: Short Inter X...Y Contact  C5     ..  C7      ..       3.17 Ang.  

PROBLEM: Short Inter X...Y Contact  C6     ..  C9      ..       3.09 Ang.  

RESPONSE: These are high pressure data - short contacts are to be 

expected





PROBLEM: _atom_site_U_iso_or_equiv is missing

RESPONSE: Topas outputs atomic displacement parameters expressed as 'B' instead

of 'U'. Isotropic B values are given below.





Low Bond Precision on  C-C Bonds ...............    0.01736 Ang.  

PROBLEM: Bond    Calc   1.728(12), Rep     1.72800 ......    Missing s.u.  

PROBLEM: Angle   Calc     92.5(6), Rep       92.50 ......    Missing s.u.  

PROBLEM: Torsion Calc   179.9(12), Rep      180.00 ......    Missing s.u.  

(Numerous)



RESPONSE: Much of the intramolecular geometry was held fixed to known

bond distances and angles (CSD: QAXMEH03)- these are not expected to change 

significantly over the course of compression. Please see the main manuscript

for discussion of intramolecular geometry.,The molecular geometry was refined using a constrained and restrained rigid body, using a Z-matrix formalism. Please see main manuscript for full details.
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
N1 N 4 -0.031(2) 0.6676(7) 0.6576(8) 1 0.14(8)
N2 N 4 -0.2464(15) 0.4872(6) 0.4035(7) 1 0.14(8)
N3 N 4 0.089(5) 0.5576(14) 0.8805(7) 1 0.14(8)
O1 O 4 0.195(6) 0.523(2) 0.9777(10) 1 0.14(8)
O2 O 4 0.046(5) 0.5052(11) 0.7851(9) 1 0.14(8)
S1 S 4 0.056(2) 0.8416(6) 0.5323(10) 1 0.14(8)
C1 C 4 -0.045(3) 0.7156(9) 0.7675(10) 1 0.14(8)
C2 C 4 -0.118(5) 0.8166(10) 0.7661(14) 1 0.14(8)
C3 C 4 -0.132(7) 0.8647(13) 0.8761(17) 1 0.14(8)
C4 C 4 -0.073(7) 0.8117(13) 0.9875(15) 1 0.14(8)
C5 C 4 -0.001(5) 0.7107(14) 0.9890(10) 1 0.14(8)
C6 C 4 0.013(4) 0.6627(12) 0.8790(8) 1 0.14(8)
C7 C 4 -0.0316(19) 0.7166(6) 0.5459(8) 1 0.14(8)
C8 C 4 -0.1009(16) 0.6730(5) 0.4319(7) 1 0.14(8)
C9 C 4 -0.084(2) 0.7410(5) 0.3324(8) 1 0.14(8)
C10 C 4 -0.001(2) 0.8352(5) 0.3721(10) 1 0.14(8)
C11 C 4 0.040(3) 0.9257(6) 0.2973(12) 1 0.14(8)
C12 C 4 -0.1819(14) 0.5696(5) 0.4161(7) 1 0.14(8)
H1 H 4 -0.006(7) 0.5910(9) 0.6559(11) 1 0.16(10)
H2 H 4 -0.163(5) 0.8572(12) 0.6808(19) 1 0.16(10)
H3 H 4 -0.188(8) 0.9420(17) 0.875(2) 1 0.16(10)
H4 H 4 -0.084(8) 0.8485(16) 1.072(2) 1 0.16(10)
H5 H 4 0.044(6) 0.6702(17) 1.0743(14) 1 0.16(10)
H9 H 4 -0.130(2) 0.7202(7) 0.2374(14) 1 0.16(10)
H111 H 4 -0.083(4) 0.9796(13) 0.287(2) 1 0.16(10)
H112 H 4 0.180(4) 0.9623(14) 0.3429(19) 1 0.16(10)
H113 H 4 0.054(5) 0.8999(8) 0.2084(18) 1 0.16(10)


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S(1) C(7) 1.728(12) . . no
S(1) C(10) 1.727(15) . . no
O(1) N(3) 1.23(3) . . no
O(2) N(3) 1.230(16) . . no
N(1) C(1) 1.384(15) . . no
N(1) C(7) 1.385(12) . . no
N(2) C(12) 1.140(11) . . no
N(3) C(6) 1.44(3) . . no
C(1) C(2) 1.39(2) . . no
C(1) C(6) 1.385(15) . . no
C(2) C(3) 1.39(3) . . no
C(3) C(4) 1.39(2) . . no
C(4) C(5) 1.38(3) . . no
C(5) C(6) 1.385(19) . . no
C(7) C(8) 1.361(11) . . no
C(8) C(9) 1.429(11) . . no
C(8) C(12) 1.430(10) . . no
C(9) C(10) 1.362(11) . . no
C(10) C(11) 1.488(14) . . no
N(1) H(1) 1.000(17) . . no
C(2) H(2) 1.06(2) . . no
C(3) H(3) 1.06(4) . . no
C(4) H(4) 1.06(3) . . no
C(5) H(5) 1.06(2) . . no
C(9) H(9) 1.060(17) . . no
C(11) H(111) 1.06(3) . . no
C(11) H(112) 1.06(3) . . no
C(11) H(113) 1.06(2) . . no



loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(7) S(1) C(10) 92.5(6) . . . no
C(1) N(1) C(7) 126.2(9) . . . no
O(1) N(3) O(2) 122(2) . . . no
O(1) N(3) C(6) 118.7(15) . . . no
O(2) N(3) C(6) 119.4(16) . . . no
N(1) C(1) C(2) 120.0(11) . . . no
N(1) C(1) C(6) 120.1(12) . . . no
C(2) C(1) C(6) 119.9(13) . . . no
C(1) C(2) C(3) 120.1(14) . . . no
C(2) C(3) C(4) 119.9(19) . . . no
C(3) C(4) C(5) 120.1(17) . . . no
C(4) C(5) C(6) 119.9(13) . . . no
N(3) C(6) C(1) 119.9(11) . . . no
N(3) C(6) C(5) 120.0(11) . . . no
C(1) C(6) C(5) 120.1(15) . . . no
S(1) C(7) N(1) 124.6(8) . . . no
S(1) C(7) C(8) 110.7(7) . . . no
N(1) C(7) C(8) 124.8(8) . . . no
C(7) C(8) C(9) 113.0(7) . . . no
C(7) C(8) C(12) 122.4(7) . . . no
C(9) C(8) C(12) 124.6(7) . . . no
C(8) C(9) C(10) 113.1(8) . . . no
S(1) C(10) C(9) 110.6(7) . . . no
S(1) C(10) C(11) 120.5(8) . . . no
C(9) C(10) C(11) 128.9(10) . . . no
N(2) C(12) C(8) 180.0(13) . . . no
C(1) N(1) H(1) 120.0(12) . . . no
C(7) N(1) H(1) 113.5(13) . . . no
C(1) C(2) H(2) 120.0(18) . . . no
C(3) C(2) H(2) 120(2) . . . no
C(2) C(3) H(3) 120(2) . . . no
C(4) C(3) H(3) 120(2) . . . no
C(3) C(4) H(4) 120(2) . . . no
C(5) C(4) H(4) 120(2) . . . no
C(4) C(5) H(5) 120(2) . . . no
C(6) C(5) H(5) 120(2) . . . no
C(8) C(9) H(9) 123.6(9) . . . no
C(10) C(9) H(9) 123.3(10) . . . no
C(10) C(11) H(111) 110.0(19) . . . no
C(10) C(11) H(112) 109.4(15) . . . no
C(10) C(11) H(113) 109.5(10) . . . no
H(111) C(11) H(112) 109.3(18) . . . no
H(111) C(11) H(113) 109(2) . . . no
H(112) C(11) H(113) 109(3) . . . no


loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C(10) S(1) C(7) N(1) 179.9(12) . . . . no
C(10) S(1) C(7) C(8) 0.0(11) . . . . no
C(7) S(1) C(10) C(9) 0.2(12) . . . . no
C(7) S(1) C(10) C(11) 179.7(13) . . . . no
C(7) N(1) C(1) C(2) 18(3) . . . . no
C(7) N(1) C(1) C(6) -162.4(18) . . . . no
C(1) N(1) C(7) S(1) 28(2) . . . . no
C(1) N(1) C(7) C(8) -151.8(15) . . . . no
O(1) N(3) C(6) C(1) 159(3) . . . . no
O(1) N(3) C(6) C(5) -21(5) . . . . no
O(2) N(3) C(6) C(1) -22(4) . . . . no
O(2) N(3) C(6) C(5) 159(3) . . . . no
N(1) C(1) C(2) C(3) -180(3) . . . . no
C(6) C(1) C(2) C(3) 0(4) . . . . no
N(1) C(1) C(6) N(3) 0(3) . . . . no
N(1) C(1) C(6) C(5) -180(2) . . . . no
C(2) C(1) C(6) N(3) -180(3) . . . . no
C(2) C(1) C(6) C(5) 0(4) . . . . no
C(1) C(2) C(3) C(4) 0(6) . . . . no
C(2) C(3) C(4) C(5) 0(6) . . . . no
C(3) C(4) C(5) C(6) 0(6) . . . . no
_exptl_crystal_colour            Orange
_exptl_crystal_recrystallization_method 'Used as supplied'
####################################################################### 
# 
# 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_OP_293K
_database_code_depnum_ccdc_archive 'CCDC 1878590'
_audit_update_record             
;
2018-11-13 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_LABEL01_ROY_OP_293K         
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_LABEL01_ROY_OP_293K_2       
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_LABEL01_ROY_OP_293K_3       
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_LABEL01_ROY_OP_293K_4       
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_LABEL01_ROY_OP_293K_5       
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_LABEL01_ROY_OP_293K_6       
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_LABEL01_ROY_OP_293K_7       
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_LABEL01_ROY_OP_293K_8       
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_LABEL01_ROY_OP_293K_9       
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
_chemical_name_common            ROY-OP
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H9 N3 O2 S'
_chemical_formula_weight         259.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_length_neutron
_atom_type_scat_source
C C 0.0000 0.0000 6.646 'Neutron Data Booklet Table 1.1-8'
H H 0.0000 0.0000 -3.739 'Neutron Data Booklet Table 1.1-8'
N N 0.0000 0.0000 9.360 'Neutron Data Booklet Table 1.1-8'
O O 0.0000 0.0000 5.805 'Neutron Data Booklet Table 1.1-8'
S S 0.0000 0.0000 2.847 'Neutron Data Booklet Table 1.1-8'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   8.011(3)
_cell_length_b                   13.395(3)
_cell_length_c                   11.726(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.759(19)
_cell_angle_gamma                90
_cell_volume                     1216.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    550
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prismatic
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_F_000             355
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          4
_exptl_crystal_size_mid          3
_exptl_crystal_size_min          2
_exptl_absorpt_coefficient_mu    0.115
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           neutron
_diffrn_radiation_details        
;
 white beam
;
_diffrn_source                   'spallation source'
_diffrn_measurement_device_type  'time-of-flight diffractometer'
_diffrn_measurement_method       'time-of-flight profile data'
_diffrn-detector                 'scintillation counters'
_diffrn_detector_area_resol_mean 0.33
_diffrn_detector_details         
;
Array of eleven flat square fiber-optically coupled scintillator PSD 
with 64 x 64 pixels and active area of 192 x 192 mm each
(resolution: 0.33 by 0.33 pixels/mm)
;
_diffrn_reflns_number            5433
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         8.047
_diffrn_reflns_theta_max         82.899
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.022
_diffrn_measured_fraction_theta_full 0.642
_diffrn_reflns_Laue_measured_fraction_max 0.022
_diffrn_reflns_Laue_measured_fraction_full 0.642
_diffrn_reflns_point_group_measured_fraction_max 0.022
_diffrn_reflns_point_group_measured_fraction_full 0.642
_reflns_number_total             5433
_reflns_number_gt                5433
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       SECI
_computing_cell_refinement       'SXD2001 (Gutmann, 2005)'
_computing_data_reduction        'SXD2001 (Gutmann, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury 3.6, (CCDC 2015)'
_computing_publication_material  'Mercury 3.6, (CCDC 2015)'

_refine_special_details          
;
 Refinement of F² against ALL unmerged Laue reflections.
 R1=0.0749 for 1820 unique reflections after merging for Fourier.
 
 CheckCIF alerts
 
PROBLEM: An _atom_site_label occurs more than once in the atom list.
PROBLEM: Duplicate Atomic Label on INPUT ................       H111 Note  
PROBLEM: Angle   Calc   108.0(16), Rep   114.8(12), Dev..       4.25 Sigma 
PROBLEM: H...A   Calc     2.60(3), Rep   2.266(14), Dev..      11.13 Sigma 
PROBLEM: D-H..A  Calc   122.8(18), Rep      161(2), Dev..      21.22 Sigma 
PROBLEM: Bond    Calc   1.087(11), Rep   1.108(10), Dev..       1.91 Sigma 

RESPONSE: The above errors all relate to geometry involving the H atoms on a
rotationally-disordered methyl group. The atom labelling of these atoms across
different disordered parts appears to give the atoms the same label, leading
to these geometric errors. Platon has not interpreted the disorder grouping 
information given below by _atom_site_disorder_assembly and 
_atom_site_disorder_group.


PROBLEM: Missing _cell_measurement_theta_min Value ......     Please Do ! 
PROBLEM: Missing _cell_measurement_theta_max Value ......     Please Do ! 

RESPONSE: Not applicable - data were measured by the time-of-flight method
using a white beam.


PROBLEM: No Datum for _diffrn_reflns_av_R_equivalents ...     Please Do ! 

RESPONSE: Not applicable - statistics on equivalent reflections are not available
as they are measured at different wavelengths. A statement regarding Rmerging 
statistics is given at the start of this section.


PROBLEM: No (Interpretable) Reflections Found in FCF ....     Please Check

RESPONSE: No action taken. The hkl reflection list is provided at the end of this CIF.


PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00491 Ang.  

RESPONSE: Noted, no action taken


PROBLEM: Short Inter XH3 .. XHn     H4       ..H113     .       2.08 Ang.  

RESPONSE: No action taken. This is short, but not impossibly so - it lies toward
the lower end of a histogram of H...H contact distances in the CSD. This error
relates to a disordered hydrogen atom on the methyl group.


PROBLEM: Long H...A H-Bond Reported H111     ..S        .       3.05 Ang.  
PROBLEM: Long D...A H-Bond Reported C11      ..S                4.08 Ang.  

RESPONSE: No action taken. This is a long C-H...S interaction.
;


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0084(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5433
_refine_ls_number_parameters     257
_refine_ls_number_restraints     73
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0686
_refine_ls_wR_factor_ref         0.1749
_refine_ls_wR_factor_gt          0.1749
_refine_ls_goodness_of_fit_ref   1.463
_refine_ls_restrained_S_all      1.467
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.0673(10) 0.8343(4) 0.5363(7) 0.0402(19) Uani 1 1 d . . . . .
O1 O 0.1687(7) 0.5404(4) 0.9874(6) 0.0749(16) Uani 1 1 d . . . . .
O2 O 0.0743(9) 0.5135(3) 0.8028(5) 0.087(2) Uani 1 1 d . . . . .
N1 N -0.0061(3) 0.67095(14) 0.6616(2) 0.0463(7) Uani 1 1 d . . . . .
N2 N -0.2255(4) 0.49975(15) 0.4254(3) 0.0609(9) Uani 1 1 d . . . . .
N3 N 0.0926(3) 0.56799(16) 0.8890(3) 0.0513(8) Uani 1 1 d . . . . .
C1 C -0.0317(4) 0.71472(17) 0.7620(3) 0.0349(8) Uani 1 1 d . . . . .
C2 C -0.1083(5) 0.81007(19) 0.7589(4) 0.0444(9) Uani 1 1 d . . . . .
C3 C -0.1316(5) 0.8554(2) 0.8598(4) 0.0552(11) Uani 1 1 d . . . . .
C4 C -0.0797(6) 0.8079(3) 0.9692(4) 0.0584(11) Uani 1 1 d . . . . .
C5 C -0.0058(5) 0.7139(3) 0.9757(4) 0.0513(10) Uani 1 1 d . . . . .
C6 C 0.0172(4) 0.66803(19) 0.8741(3) 0.0382(8) Uani 1 1 d . . . . .
C7 C -0.0208(4) 0.71849(17) 0.5538(3) 0.0368(8) Uani 1 1 d . . . . .
C8 C -0.0872(4) 0.67510(17) 0.4449(3) 0.0361(8) Uani 1 1 d . . . . .
C9 C -0.0689(4) 0.73669(19) 0.3485(4) 0.0391(8) Uani 1 1 d . . . . .
C10 C 0.0113(4) 0.82569(18) 0.3849(3) 0.0376(8) Uani 1 1 d . . . . .
C11 C 0.0490(4) 0.9103(2) 0.3110(3) 0.0512(10) Uani 1 1 d D . . . .
C12 C -0.1651(4) 0.57853(18) 0.4336(3) 0.0416(9) Uani 1 1 d . . . . .
H1 H 0.0316(11) 0.5985(4) 0.6676(7) 0.072(2) Uani 1 1 d . . . . .
H2 H -0.1506(11) 0.8473(5) 0.6741(8) 0.071(2) Uani 1 1 d . . . . .
H3 H -0.1932(13) 0.9286(5) 0.8533(10) 0.092(3) Uani 1 1 d . . . . .
H4 H -0.1035(15) 0.8441(7) 1.0469(10) 0.101(4) Uani 1 1 d . . . . .
H5 H 0.0311(13) 0.6728(7) 1.0578(10) 0.084(3) Uani 1 1 d . . . . .
H9 H -0.1150(12) 0.7148(5) 0.2577(9) 0.068(2) Uani 1 1 d . . . . .
H111 H 0.060(5) 0.9823(11) 0.357(2) 0.062(7) Uiso 0.28(3) 1 d D U P A 1
H112 H 0.170(3) 0.899(2) 0.285(3) 0.062(7) Uiso 0.28(3) 1 d D U P A 1
H113 H -0.056(3) 0.917(2) 0.230(2) 0.062(7) Uiso 0.28(3) 1 d D U P A 1
H111 H -0.022(4) 0.9769(11) 0.329(3) 0.065(5) Uiso 0.39(3) 1 d D U P B 2
H112 H 0.1859(13) 0.9293(19) 0.333(3) 0.065(5) Uiso 0.39(3) 1 d D U P B 2
H113 H 0.004(4) 0.8936(16) 0.2175(9) 0.065(5) Uiso 0.39(3) 1 d D U P B 2
H111 H -0.0619(19) 0.9568(19) 0.271(3) 0.069(6) Uiso 0.33(3) 1 d D U P C 3
H112 H 0.153(3) 0.9580(19) 0.360(2) 0.069(6) Uiso 0.33(3) 1 d D U P C 3
H113 H 0.095(5) 0.8753(14) 0.239(2) 0.069(6) Uiso 0.33(3) 1 d D U P C 3

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
S 0.058(5) 0.030(2) 0.029(5) -0.002(3) 0.006(4) -0.002(2)
O1 0.071(3) 0.086(3) 0.064(5) 0.032(3) 0.009(4) 0.018(2)
O2 0.160(6) 0.0470(18) 0.060(4) 0.015(2) 0.040(5) 0.033(3)
N1 0.0757(18) 0.0321(8) 0.0323(17) 0.0008(8) 0.0161(15) 0.0075(9)
N2 0.0635(17) 0.0420(10) 0.069(2) -0.0059(12) 0.0026(18) -0.0137(10)
N3 0.0550(16) 0.0524(11) 0.050(2) 0.0173(12) 0.0190(17) 0.0087(10)
C1 0.0396(17) 0.0347(10) 0.031(2) -0.0009(11) 0.0093(17) -0.0011(10)
C2 0.053(2) 0.0371(12) 0.047(3) -0.0008(14) 0.019(2) 0.0039(12)
C3 0.070(2) 0.0478(14) 0.058(3) -0.0099(16) 0.035(3) 0.0017(15)
C4 0.074(3) 0.0681(19) 0.040(3) -0.0133(18) 0.028(3) -0.0033(17)
C5 0.049(2) 0.0714(19) 0.034(3) -0.0039(18) 0.013(2) -0.0032(16)
C6 0.0351(17) 0.0467(13) 0.033(2) 0.0027(13) 0.0094(17) -0.0032(11)
C7 0.0495(18) 0.0301(9) 0.031(2) -0.0007(11) 0.0105(17) 0.0046(10)
C8 0.0397(17) 0.0333(11) 0.033(2) -0.0033(12) 0.0053(17) 0.0025(10)
C9 0.0416(18) 0.0416(12) 0.030(3) -0.0003(13) 0.0011(18) 0.0032(11)
C10 0.0412(17) 0.0364(11) 0.033(2) 0.0016(12) 0.0052(17) 0.0023(10)
C11 0.058(2) 0.0533(15) 0.039(3) 0.0151(15) 0.006(2) -0.0048(14)
C12 0.0463(19) 0.0338(11) 0.040(2) -0.0042(12) 0.0022(19) -0.0013(11)
H1 0.124(7) 0.037(2) 0.059(6) 0.002(3) 0.030(6) 0.016(3)
H2 0.104(6) 0.060(3) 0.056(6) 0.014(4) 0.032(5) 0.029(4)
H3 0.129(8) 0.060(3) 0.107(9) -0.002(4) 0.067(8) 0.026(4)
H4 0.143(9) 0.106(6) 0.069(8) -0.029(5) 0.055(8) 0.007(6)
H5 0.103(7) 0.103(6) 0.053(7) 0.010(5) 0.031(6) 0.006(5)
H9 0.086(6) 0.076(4) 0.033(6) -0.004(4) -0.002(5) -0.011(4)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S C10 1.721(9) . ?
S C7 1.738(6) . ?
O1 N3 1.217(7) . ?
O2 N3 1.225(6) . ?
N1 C1 1.377(4) . ?
N1 C7 1.393(4) . ?
N1 H1 1.014(6) . ?
N2 C12 1.155(3) . ?
N3 C6 1.462(4) . ?
C1 C2 1.413(4) . ?
C1 C6 1.417(5) . ?
C2 C3 1.384(5) . ?
C2 H2 1.087(11) . ?
C3 C4 1.397(6) . ?
C3 H3 1.092(7) . ?
C4 C5 1.386(5) . ?
C4 H4 1.092(9) . ?
C5 C6 1.394(5) . ?
C5 H5 1.083(13) . ?
C7 C8 1.380(5) . ?
C8 C12 1.427(4) . ?
C8 C9 1.437(4) . ?
C9 C10 1.370(4) . ?
C9 H9 1.075(12) . ?
C10 C11 1.503(4) . ?
C11 H111 1.100(10) . ?
C11 H112 1.101(10) . ?
C11 H113 1.097(10) . ?
C11 H111 1.108(9) . ?
C11 H112 1.091(9) . ?
C11 H113 1.087(10) . ?
C11 H111 1.090(10) . ?
C11 H112 1.095(10) . ?
C11 H113 1.108(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 S C7 93.1(4) . . ?
C1 N1 C7 125.8(2) . . ?
C1 N1 H1 117.0(5) . . ?
C7 N1 H1 117.2(5) . . ?
O1 N3 O2 121.8(4) . . ?
O1 N3 C6 118.9(4) . . ?
O2 N3 C6 119.2(4) . . ?
N1 C1 C2 121.4(3) . . ?
N1 C1 C6 122.6(2) . . ?
C2 C1 C6 116.0(3) . . ?
C3 C2 C1 121.8(4) . . ?
C3 C2 H2 120.1(4) . . ?
C1 C2 H2 118.1(4) . . ?
C2 C3 C4 120.8(3) . . ?
C2 C3 H3 119.5(7) . . ?
C4 C3 H3 119.8(6) . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 H4 121.4(8) . . ?
C3 C4 H4 119.4(7) . . ?
C4 C5 C6 120.0(4) . . ?
C4 C5 H5 121.8(6) . . ?
C6 C5 H5 118.1(6) . . ?
C5 C6 C1 122.2(3) . . ?
C5 C6 N3 116.2(3) . . ?
C1 C6 N3 121.6(3) . . ?
C8 C7 N1 124.8(2) . . ?
C8 C7 S 109.8(3) . . ?
N1 C7 S 124.9(4) . . ?
C7 C8 C12 121.6(3) . . ?
C7 C8 C9 113.2(2) . . ?
C12 C8 C9 125.2(3) . . ?
C10 C9 C8 112.8(3) . . ?
C10 C9 H9 124.2(5) . . ?
C8 C9 H9 123.0(4) . . ?
C9 C10 C11 128.6(4) . . ?
C9 C10 S 111.0(3) . . ?
C11 C10 S 120.4(3) . . ?
C10 C11 H111 112.2(13) . . ?
C10 C11 H112 112.0(12) . . ?
H111 C11 H112 107.1(10) . . ?
C10 C11 H113 109.7(13) . . ?
H111 C11 H113 107.7(10) . . ?
H112 C11 H113 107.9(10) . . ?
C10 C11 H111 107.9(10) . . ?
C10 C11 H112 112.2(10) . . ?
H111 C11 H112 107.6(9) . . ?
C10 C11 H113 111.2(9) . . ?
H111 C11 H113 107.8(9) . . ?
H112 C11 H113 110.0(9) . . ?
C10 C11 H111 114.8(12) . . ?
C10 C11 H112 111.9(13) . . ?
H111 C11 H112 108.9(10) . . ?
C10 C11 H113 106.0(11) . . ?
H111 C11 H113 107.5(10) . . ?
H112 C11 H113 107.2(9) . . ?
N2 C12 C8 178.9(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C7 S 46.2(5) . . . . ?
C2 C1 N1 C7 12.2(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 1.014(6) 1.911(9) 2.658(5) 128.0(6) .
N1 H1 N2 1.014(6) 2.490(7) 3.267(3) 133.1(5) 3_566
C2 H2 S 1.087(11) 2.669(10) 3.281(8) 115.1(5) .
C11 H112 O1 1.095(10) 2.266(14) 3.319(7) 161(2) 2_556
C11 H113 N2 1.097(10) 2.450(17) 3.489(5) 158(2) 2_455
C11 H112 O1 1.095(10) 2.266(14) 3.319(7) 161(2) 2_556
C11 H111 S 1.100(10) 3.05(2) 4.078(7) 156(3) 3_576
C11 H113 N2 1.097(10) 2.450(17) 3.489(5) 158(2) 2_455

_refine_diff_density_max         0.935
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.140

_shelx_res_file                  
;

    roy_rt2.res created by SHELXL-2014/7


TITL ROY-OP orange at RT SXD 3D integration
CELL 0.7   8.0110   13.3949   11.7262   90.0000  104.7594   90.0000
ZERR  4.0   0.0025    0.0033    0.0039    0.000     0.019   0.000
LATT  1
SYMM 1/2-x,1/2+y,1/2-z
SFAC  C   0 0 0 0 0 0 0 0  6.64800   0.000   0.000     0.035   0.76   12.010
SFAC  H   0 0 0 0 0 0 0 0 -3.74100   0.000   0.000     38.00   0.31    1.008
SFAC  N   0 0 0 0 0 0 0 0  9.36000   0.000   0.000     1.90    0.70   14.007
SFAC  O   0 0 0 0 0 0 0 0  5.80500   0.000   0.000     0.0019  0.66   15.999
SFAC  S   0 0 0 0 0 0 0 0  2.84700   0.000   0.000     0.52    1.02   32.065
UNIT 48 36 12 8 4

L.S. 5
BOND $H
REM Instructions for hydrogen bonds with esds
HTAB N1 O2
EQIV $1 -x, -y+1, -z+1
HTAB N1 N2_$1
HTAB C2 S
EQIV $2 -x+1/2, y+1/2, -z+3/2
HTAB C11 O1_$2
EQIV $3 -x-1/2, y+1/2, -z+1/2
HTAB C11 N2_$3
HTAB C11 O1_$2
EQIV $4 -x, -y+2, -z+1
HTAB C11 S_$4
HTAB C11 N2_$3

CONF C1 N1 C7 S
CONF C2 C1 N1 C7
MPLA C1 C2 C3 C4 C5 C6
MPLA S C7 C8 C9 C10

ACTA
MERG 0
FMAP -2
PLAN 10
temp 20

omit   1  -1  -1
omit  -2   1  -1
omit  -2   3   4
omit  -1   5   3
omit  -1   1   4
omit  -6  -3   6
omit   1   2   1
omit   0  -1   2
omit  -5  -9   4
omit  -3  24  -2
omit   3 -20   3
omit  -2  33  -6
omit   5  12   0
omit  -3  19   1
omit -15 -14  21
omit   4   4   2
omit  -2  -4   0
omit  -3   0   3
omit  -1   5   2
omit   1   4  -1
omit  -5  -2  -5
omit  -2  -7   2
omit  -3 -19   1
omit  -2 -11  15
omit  -7  13   4
omit  -4  18   0

sadi 0.007 C11 H111 c11 h112 c11 h113
sadi 0.007 h111 h112 h111 h113 h112 h113

sump 1 0.01 1.0 2 1.0 3 1.0 4

WGHT    0.100000
EXTI    0.008420
BASF   1.21962   1.22813   1.03557   1.01328   1.22865   1.00000
FVAR       0.29566   0.28209   0.39365   0.32548   0.06170   0.06474   0.06913
S     5    0.067265    0.834309    0.536316    11.00000    0.05850    0.03041 =
         0.02875   -0.00196    0.00573   -0.00199
O1    4    0.168678    0.540418    0.987429    11.00000    0.07074    0.08557 =
         0.06380    0.03231    0.00882    0.01824
O2    4    0.074258    0.513473    0.802847    11.00000    0.15966    0.04703 =
         0.06015    0.01538    0.03954    0.03333
N1    3   -0.006109    0.670954    0.661563    11.00000    0.07566    0.03213 =
         0.03226    0.00078    0.01606    0.00746
N2    3   -0.225532    0.499748    0.425403    11.00000    0.06348    0.04203 =
         0.06927   -0.00592    0.00263   -0.01367
N3    3    0.092643    0.567987    0.889047    11.00000    0.05501    0.05238 =
         0.04958    0.01727    0.01903    0.00872
C1    1   -0.031724    0.714717    0.762018    11.00000    0.03955    0.03472 =
         0.03069   -0.00090    0.00929   -0.00109
C2    1   -0.108331    0.810070    0.758886    11.00000    0.05326    0.03712 =
         0.04658   -0.00084    0.01943    0.00387
C3    1   -0.131597    0.855440    0.859760    11.00000    0.06959    0.04780 =
         0.05835   -0.00989    0.03466    0.00174
C4    1   -0.079725    0.807930    0.969176    11.00000    0.07366    0.06813 =
         0.04046   -0.01332    0.02753   -0.00333
C5    1   -0.005802    0.713866    0.975726    11.00000    0.04944    0.07141 =
         0.03413   -0.00390    0.01270   -0.00315
C6    1    0.017197    0.668027    0.874082    11.00000    0.03515    0.04669 =
         0.03317    0.00271    0.00938   -0.00318
C7    1   -0.020817    0.718489    0.553788    11.00000    0.04950    0.03006 =
         0.03112   -0.00068    0.01054    0.00458
C8    1   -0.087250    0.675097    0.444930    11.00000    0.03969    0.03326 =
         0.03320   -0.00333    0.00526    0.00245
C9    1   -0.068920    0.736692    0.348470    11.00000    0.04159    0.04158 =
         0.02974   -0.00032    0.00107    0.00321
C10   1    0.011277    0.825695    0.384896    11.00000    0.04122    0.03638 =
         0.03299    0.00161    0.00524    0.00229
C11   1    0.049012    0.910290    0.310983    11.00000    0.05801    0.05334 =
         0.03867    0.01508    0.00598   -0.00476
C12   1   -0.165055    0.578530    0.433620    11.00000    0.04635    0.03377 =
         0.03980   -0.00422    0.00217   -0.00133
H1    2    0.031598    0.598501    0.667645    11.00000    0.12396    0.03712 =
         0.05880    0.00239    0.02974    0.01599
H2    2   -0.150642    0.847318    0.674073    11.00000    0.10424    0.05981 =
         0.05598    0.01426    0.03170    0.02927
H3    2   -0.193217    0.928630    0.853293    11.00000    0.12861    0.05989 =
         0.10702   -0.00163    0.06675    0.02634
H4    2   -0.103548    0.844149    1.046942    11.00000    0.14252    0.10631 =
         0.06917   -0.02857    0.05481    0.00702
H5    2    0.031109    0.672764    1.057817    11.00000    0.10268    0.10290 =
         0.05318    0.00972    0.03098    0.00603
H9    2   -0.114986    0.714782    0.257681    11.00000    0.08577    0.07596 =
         0.03258   -0.00368   -0.00162   -0.01072
rem
rem rotationally disordered methyl group
part 1
H111  2    0.060120    0.982303    0.357418    21.00000   51.00000
H112  2    0.170329    0.898736    0.285070    21.00000   51.00000
H113  2   -0.055609    0.916903    0.230139    21.00000   51.00000
part 2
H111  2   -0.021987    0.976893    0.329258    31.00000   61.00000
H112  2    0.185944    0.929281    0.332803    31.00000   61.00000
H113  2    0.003782    0.893592    0.217489    31.00000   61.00000
part 3
H111  2   -0.061941    0.956827    0.270630    41.00000   71.00000
H112  2    0.153426    0.958042    0.360465    41.00000   71.00000
H113  2    0.094679    0.875350    0.238742    41.00000   71.00000
part 0

hklf 2

REM  ROY-OP orange at RT SXD 3D integration
REM R1 =  0.0686 for    5433 Fo > 4sig(Fo)  and  0.0686 for all    5433 data
REM    257 parameters refined using     73 restraints

END

WGHT      0.1010      8.5044

REM Highest difference peak  0.935,  deepest hole -0.629,  1-sigma level  0.140
Q1    1  -0.0390  0.6711  0.5813  11.00000  0.05    0.94
Q2    1  -0.0998  0.6758  0.3720  11.00000  0.05    0.70
Q3    1  -0.0514  0.7190  0.6862  11.00000  0.05    0.67
Q4    1   0.0377  0.6720  1.0114  11.00000  0.05    0.64
Q5    1  -0.1217  0.4798  0.4589  11.00000  0.05   -0.63
Q6    1  -0.0018  0.9002  0.1809  11.00000  0.05    0.59
Q7    1  -0.0133  0.7343  0.4287  11.00000  0.05    0.58
Q8    1   0.2275  0.9313  0.3786  11.00000  0.05   -0.58
Q9    1   0.0000  0.5000  0.5000  10.50000  0.05   -0.57
Q10   1  -0.0205  0.6722  0.7992  11.00000  0.05    0.57
;
_shelx_res_checksum              18681
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ROY_OP_150K
_database_code_depnum_ccdc_archive 'CCDC 1878591'
_audit_update_record             
;
2018-11-13 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_LABEL01_ROY_OP_150K         
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_LABEL01_ROY_OP_150K_2       
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_LABEL01_ROY_OP_150K_3       
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_LABEL01_ROY_OP_150K_4       
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_LABEL01_ROY_OP_150K_5       
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_LABEL01_ROY_OP_150K_6       
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_LABEL01_ROY_OP_150K_7       
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_LABEL01_ROY_OP_150K_8       
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_LABEL01_ROY_OP_150K_9       
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_DIFMN02_ROY_OP_150K         
;
PROBLEM: he minimum difference density is < -0.1*zmax*0.75="" _refine_diff_density_min="" given="-1.271" test="" value="-1.200"><a href='javascript:makeHelpWindow("DIFMN_03.html")'>DIFMN03_ALERT_1_C</a> The minimum difference density is < -0.1*zmax*0.75="" the="" relevant="" atom="" site="" should="" be="" identified.=""><a href='javascript:makeHelpWindow("DIFMX_02.html")'>DIFMX02_ALERT_1_C</a> The maximum difference density is > 0.1*ZMAX*0.75
RESPONSE: This alert relates to residual electron density, however our difference maps are calculated from nuclear scattering density. Residual positive and negative densities have approximately the same magnitude. Furthermore, the molecular structure is known and any ambiguities in atomic positioning are going to be most significant around the rotationally disordered methyl group
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
_chemical_name_common            ROY-OP
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H9 N3 O2 S'
_chemical_formula_weight         259.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_length_neutron
_atom_type_scat_source
C C 0.0000 0.0000 6.646 'Neutron Data Booklet Table 1.1-8'
H H 0.0000 0.0000 -3.739 'Neutron Data Booklet Table 1.1-8'
N N 0.0000 0.0000 9.360 'Neutron Data Booklet Table 1.1-8'
O O 0.0000 0.0000 5.805 'Neutron Data Booklet Table 1.1-8'
S S 0.0000 0.0000 2.847 'Neutron Data Booklet Table 1.1-8'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   7.765(3)
_cell_length_b                   13.283(3)
_cell_length_c                   11.615(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.140(19)
_cell_angle_gamma                90
_cell_volume                     1161.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    550
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prismatic
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_F_000             355
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          4
_exptl_crystal_size_mid          3
_exptl_crystal_size_min          2
_exptl_absorpt_coefficient_mu    0.120
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_type           neutron
_diffrn_radiation_details        
;
 white beam
;
_diffrn_source                   'spallation source'
_diffrn_measurement_device_type  'time-of-flight diffractometer'
_diffrn_measurement_method       'time-of-flight profile data'
_diffrn-detector                 'scintillation counters'
_diffrn_detector_area_resol_mean 0.33
_diffrn_detector_details         
;
Array of eleven flat square fiber-optically coupled scintillator PSD 
with 64 x 64 pixels and active area of 192 x 192 mm each
(resolution: 0.33 by 0.33 pixels/mm)
;
_diffrn_reflns_number            7180
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         8.617
_diffrn_reflns_theta_max         86.810
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.215
_diffrn_measured_fraction_theta_full 0.732
_diffrn_reflns_Laue_measured_fraction_max 0.215
_diffrn_reflns_Laue_measured_fraction_full 0.732
_diffrn_reflns_point_group_measured_fraction_max 0.215
_diffrn_reflns_point_group_measured_fraction_full 0.732
_reflns_number_total             7180
_reflns_number_gt                7180
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       SECI
_computing_cell_refinement       'SXD2001 (Gutmann, 2005)'
_computing_data_reduction        'SXD2001 (Gutmann, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury 3.6, (CCDC 2015)'
_computing_publication_material  'Mercury 3.6, (CCDC 2015)'

_refine_special_details          
;
 Refinement of F² against ALL unmerged Laue reflections.
 R1=0.0605 for 2854 unique reflections after merging for Fourier.
 
 CheckCIF alerts
 
PROBLEM: An _atom_site_label occurs more than once in the atom list.
PROBLEM: Duplicate Atomic Label on INPUT ................       H111 Note  
PROBLEM: Angle   Calc    114.4(9), Rep    111.6(7), Dev..       3.11 Sigma 
PROBLEM: H...A   Calc     3.66(2), Rep    2.863(9), Dev..      39.85 Sigma 
PROBLEM: D-H..A  Calc    98.7(12), Rep   175.8(13), Dev..      64.25 Sigma 
PROBLEM: Bond    Calc   1.116(17), Rep    1.092(8), Dev..       1.41 Sigma 
PROBLEM: D-H     Calc   1.088(17), Rep    1.110(8), Dev..       1.29 Sigma 

RESPONSE: The above errors all relate to geometry involving the H atoms on a
rotationally-disordered methyl group. The atom labelling of these atoms across
different disordered parts appears to give the atoms the same label, leading
to these geometric errors. Platon has not interpreted the disorder grouping 
information given below by _atom_site_disorder_assembly and 
_atom_site_disorder_group.


PROBLEM: The minimum difference density is < -0.1*ZMAX*0.75
PROBLEM: The maximum difference density is > 0.1*ZMAX*0.75

RESPONSE: These alerts relate to residual electron density, however
our difference maps are calculated from nuclear scattering density. Residual
positive and negative densities have approximately the same magnitude.
Furthermore, the molecular structure is known and any ambiguities in atomic
positioning are going to be most significant around the rotationally 
disordered methyl group.


PROBLEM: Missing _cell_measurement_theta_min Value ......     Please Do ! 
PROBLEM: Missing _cell_measurement_theta_max Value ......     Please Do ! 

RESPONSE: Not applicable - data were measured by the time-of-flight method
using a white beam.


PROBLEM: No Datum for _diffrn_reflns_av_R_equivalents ...     Please Do ! 

RESPONSE: Not applicable - statistics on equivalent reflections are not available
as they are measured at different wavelengths. A statement regarding Rmerging 
statistics is given at the start of this section.


PROBLEM: No (Interpretable) Reflections Found in FCF ....     Please Check

RESPONSE: No action taken. The hkl reflection list is provided at the end of this CIF.


PROBLEM: Short Inter XH3 .. XHn     H4       ..H113     .       2.11 Ang.  

RESPONSE: No action taken. This is short, but not impossibly so - it lies toward
the lower end of a histogram of H...H contact distances in the CSD. This error
relates to a disordered hydrogen atom on the methyl group.

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0060(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7180
_refine_ls_number_parameters     255
_refine_ls_number_restraints     73
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0673
_refine_ls_wR_factor_ref         0.1795
_refine_ls_wR_factor_gt          0.1795
_refine_ls_goodness_of_fit_ref   1.498
_refine_ls_restrained_S_all      1.515
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.0682(5) 0.8372(3) 0.5363(6) 0.0194(11) Uani 1 1 d . . . . .
O1 O 0.1712(3) 0.5397(2) 0.9873(3) 0.0348(8) Uani 1 1 d . . . . .
O2 O 0.0687(5) 0.5120(2) 0.8001(4) 0.0417(9) Uani 1 1 d . . . . .
N1 N -0.00754(18) 0.67163(11) 0.66040(18) 0.0222(4) Uani 1 1 d . . . . .
N2 N -0.22478(18) 0.49912(11) 0.4242(2) 0.0293(5) Uani 1 1 d . . . . .
N3 N 0.09116(17) 0.56730(12) 0.88834(19) 0.0249(4) Uani 1 1 d . . . . .
C1 C -0.03262(19) 0.71560(14) 0.7625(2) 0.0168(5) Uani 1 1 d . . . . .
C2 C -0.1098(2) 0.81185(15) 0.7599(3) 0.0206(5) Uani 1 1 d . . . . .
C3 C -0.1320(2) 0.85739(16) 0.8621(3) 0.0261(6) Uani 1 1 d . . . . .
C4 C -0.0787(3) 0.80915(19) 0.9718(3) 0.0285(6) Uani 1 1 d . . . . .
C5 C -0.0047(2) 0.71426(18) 0.9773(3) 0.0247(5) Uani 1 1 d . . . . .
C6 C 0.0170(2) 0.66793(15) 0.8745(2) 0.0181(5) Uani 1 1 d . . . . .
C7 C -0.0205(2) 0.71978(13) 0.5531(2) 0.0172(4) Uani 1 1 d . . . . .
C8 C -0.0858(2) 0.67618(13) 0.4433(2) 0.0168(4) Uani 1 1 d . . . . .
C9 C -0.0662(2) 0.73827(15) 0.3472(2) 0.0183(5) Uani 1 1 d . . . . .
C10 C 0.0122(2) 0.82820(14) 0.3838(2) 0.0182(5) Uani 1 1 d . . . . .
C11 C 0.0490(2) 0.91369(16) 0.3098(2) 0.0249(6) Uani 1 1 d D . . . .
C12 C -0.1640(2) 0.57905(14) 0.4321(2) 0.0204(5) Uani 1 1 d . . . . .
H1 H 0.0304(7) 0.5987(3) 0.6661(7) 0.0422(14) Uani 1 1 d . . . . .
H2 H -0.1553(6) 0.8497(4) 0.6750(6) 0.0390(13) Uani 1 1 d . . . . .
H3 H -0.1951(8) 0.9309(4) 0.8557(7) 0.0499(17) Uani 1 1 d . . . . .
H4 H -0.1019(9) 0.8451(5) 1.0498(7) 0.0540(17) Uani 1 1 d . . . . .
H5 H 0.0333(7) 0.6726(5) 1.0608(7) 0.0458(14) Uani 1 1 d . . . . .
H9 H -0.1113(6) 0.7159(4) 0.2556(6) 0.0413(14) Uani 1 1 d . . . . .
H111 H -0.0410(14) 0.9773(7) 0.3107(15) 0.032(3) Uiso 0.39(2) 1 d D U P A 1
H112 H 0.1855(10) 0.9423(10) 0.3430(13) 0.032(3) Uiso 0.39(2) 1 d D U P A 1
H113 H 0.0344(18) 0.8902(8) 0.2178(8) 0.032(3) Uiso 0.39(2) 1 d D U P A 1
H111 H -0.0691(14) 0.9526(14) 0.2600(19) 0.041(4) Uiso 0.253(18) 1 d D U P B 2
H112 H 0.143(2) 0.9698(13) 0.3585(17) 0.041(4) Uiso 0.253(18) 1 d D U P B 2
H113 H 0.114(2) 0.8806(13) 0.2428(16) 0.041(4) Uiso 0.253(18) 1 d D U P B 2
H111 H 0.017(2) 0.9856(9) 0.3486(15) 0.044(3) Uiso 0.36(2) 1 d D U P C 3
H112 H 0.1860(10) 0.9181(12) 0.3044(16) 0.044(3) Uiso 0.36(2) 1 d D U P C 3
H113 H -0.0389(18) 0.9087(12) 0.2213(10) 0.044(3) Uiso 0.36(2) 1 d D U P C 3

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
S 0.0272(16) 0.0158(18) 0.015(3) 0.000(2) 0.0052(17) -0.0003(12)
O1 0.0322(10) 0.0410(15) 0.028(2) 0.0128(16) 0.0016(11) 0.0085(9)
O2 0.078(2) 0.0225(13) 0.027(3) 0.0059(15) 0.0163(16) 0.0154(12)
N1 0.0357(6) 0.0152(6) 0.0168(11) 0.0003(7) 0.0084(6) 0.0035(4)
N2 0.0292(5) 0.0190(6) 0.0357(14) -0.0017(8) 0.0005(6) -0.0049(4)
N3 0.0256(5) 0.0268(7) 0.0241(12) 0.0077(8) 0.0094(6) 0.0045(5)
C1 0.0185(6) 0.0161(7) 0.0159(14) -0.0005(8) 0.0043(6) -0.0014(5)
C2 0.0255(7) 0.0179(8) 0.0202(15) -0.0015(9) 0.0091(7) 0.0006(6)
C3 0.0299(8) 0.0231(9) 0.0293(18) -0.0060(11) 0.0146(9) 0.0003(6)
C4 0.0345(9) 0.0333(12) 0.0210(18) -0.0086(12) 0.0130(9) -0.0026(8)
C5 0.0238(7) 0.0329(11) 0.0182(16) -0.0002(11) 0.0068(7) -0.0011(7)
C6 0.0171(6) 0.0227(8) 0.0152(14) -0.0001(9) 0.0051(6) -0.0022(5)
C7 0.0213(6) 0.0140(7) 0.0161(13) -0.0008(9) 0.0043(6) 0.0014(5)
C8 0.0188(6) 0.0146(7) 0.0164(13) -0.0015(8) 0.0031(6) 0.0013(5)
C9 0.0209(6) 0.0196(8) 0.0127(14) 0.0011(9) 0.0009(6) 0.0017(5)
C10 0.0199(6) 0.0168(8) 0.0170(14) 0.0019(9) 0.0027(7) 0.0010(5)
C11 0.0275(8) 0.0253(10) 0.0192(16) 0.0079(10) 0.0008(8) -0.0030(6)
C12 0.0210(6) 0.0157(8) 0.0225(15) -0.0017(9) 0.0016(7) -0.0008(5)
H1 0.070(3) 0.0220(19) 0.037(4) 0.004(2) 0.017(3) 0.0105(18)
H2 0.051(2) 0.035(2) 0.032(4) 0.003(3) 0.013(2) 0.0121(18)
H3 0.069(3) 0.034(2) 0.056(5) -0.006(3) 0.033(3) 0.012(2)
H4 0.075(3) 0.058(3) 0.035(5) -0.012(4) 0.025(3) 0.009(3)
H5 0.053(2) 0.060(3) 0.025(4) 0.007(3) 0.010(2) 0.008(2)
H9 0.047(2) 0.046(3) 0.026(4) -0.005(3) -0.003(2) -0.0070(18)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S C10 1.721(7) . ?
S C7 1.734(5) . ?
O1 N3 1.222(4) . ?
O2 N3 1.238(4) . ?
N1 C1 1.377(3) . ?
N1 C7 1.383(3) . ?
N1 H1 1.009(5) . ?
N2 C12 1.157(2) . ?
N3 C6 1.449(2) . ?
C1 C2 1.409(3) . ?
C1 C6 1.413(3) . ?
C2 C3 1.380(4) . ?
C2 H2 1.086(7) . ?
C3 C4 1.395(4) . ?
C3 H3 1.087(5) . ?
C4 C5 1.380(3) . ?
C4 H4 1.077(8) . ?
C5 C6 1.389(4) . ?
C5 H5 1.093(8) . ?
C7 C8 1.379(3) . ?
C8 C12 1.418(3) . ?
C8 C9 1.426(3) . ?
C9 C10 1.361(3) . ?
C9 H9 1.077(7) . ?
C10 C11 1.493(3) . ?
C11 H111 1.098(7) . ?
C11 H112 1.103(6) . ?
C11 H113 1.092(8) . ?
C11 H111 1.088(8) . ?
C11 H112 1.097(8) . ?
C11 H113 1.116(9) . ?
C11 H111 1.110(8) . ?
C11 H112 1.083(7) . ?
C11 H113 1.088(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 S C7 92.6(3) . . ?
C1 N1 C7 125.84(15) . . ?
C1 N1 H1 116.8(5) . . ?
C7 N1 H1 117.3(4) . . ?
O1 N3 O2 122.5(2) . . ?
O1 N3 C6 118.6(2) . . ?
O2 N3 C6 118.9(2) . . ?
N1 C1 C2 121.0(2) . . ?
N1 C1 C6 122.57(16) . . ?
C2 C1 C6 116.4(2) . . ?
C3 C2 C1 121.4(2) . . ?
C3 C2 H2 119.8(3) . . ?
C1 C2 H2 118.8(4) . . ?
C2 C3 C4 120.8(2) . . ?
C2 C3 H3 118.9(5) . . ?
C4 C3 H3 120.2(5) . . ?
C5 C4 C3 119.2(3) . . ?
C5 C4 H4 121.3(5) . . ?
C3 C4 H4 119.4(5) . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5 121.5(4) . . ?
C6 C5 H5 118.3(4) . . ?
C5 C6 C1 121.98(19) . . ?
C5 C6 N3 116.2(2) . . ?
C1 C6 N3 121.8(2) . . ?
C8 C7 N1 124.63(17) . . ?
C8 C7 S 109.9(3) . . ?
N1 C7 S 125.0(3) . . ?
C7 C8 C12 121.3(2) . . ?
C7 C8 C9 113.28(17) . . ?
C12 C8 C9 125.4(2) . . ?
C10 C9 C8 112.8(2) . . ?
C10 C9 H9 124.3(4) . . ?
C8 C9 H9 122.9(4) . . ?
C9 C10 C11 128.4(2) . . ?
C9 C10 S 111.3(2) . . ?
C11 C10 S 120.3(2) . . ?
C10 C11 H111 111.6(7) . . ?
C10 C11 H112 111.3(7) . . ?
H111 C11 H112 106.9(6) . . ?
C10 C11 H113 110.9(6) . . ?
H111 C11 H113 108.4(7) . . ?
H112 C11 H113 107.6(7) . . ?
C10 C11 H111 114.4(10) . . ?
C10 C11 H112 114.6(12) . . ?
H111 C11 H112 108.5(9) . . ?
C10 C11 H113 106.5(11) . . ?
H111 C11 H113 106.4(9) . . ?
H112 C11 H113 105.8(9) . . ?
C10 C11 H111 109.1(9) . . ?
C10 C11 H112 113.8(9) . . ?
H111 C11 H112 107.4(8) . . ?
C10 C11 H113 109.5(8) . . ?
H111 C11 H113 106.5(8) . . ?
H112 C11 H113 110.3(9) . . ?
N2 C12 C8 178.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C7 S 44.1(3) . . . . ?
C2 C1 N1 C7 12.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 1.009(5) 1.900(8) 2.647(4) 128.3(6) .
N1 H1 N2 1.009(5) 2.417(6) 3.199(2) 133.7(5) 3_566
C2 H2 S 1.086(7) 2.646(8) 3.244(7) 114.0(3) .
C11 H112 O1 1.097(8) 2.213(11) 3.252(4) 157.3(17) 2_556
C11 H111 N2 1.088(8) 2.418(14) 3.416(3) 151.8(17) 2_455
C11 H112 O1 1.097(8) 2.213(11) 3.252(4) 157.3(17) 2_556
C11 H111 S 1.110(8) 2.863(9) 3.971(6) 175.8(13) 3_576
C11 H111 N2 1.088(8) 2.418(14) 3.416(3) 151.8(17) 2_455

_refine_diff_density_max         1.206
_refine_diff_density_min         -1.271
_refine_diff_density_rms         0.257

_shelx_res_file                  
;

    roy150_3d.res created by SHELXL-2014/7


TITL ROY-OP orange at 150K SXD 3D integration
CELL 0.7    7.7652   13.2832   11.6145   90.0000  104.140   90.0000
ZERR  4.0   0.0025    0.0033    0.0039    0.000     0.019   0.000
LATT  1
SYMM 1/2-x,1/2+y,1/2-z
SFAC  C   0 0 0 0 0 0 0 0  6.64800   0.000   0.000     0.035   0.76   12.010
SFAC  H   0 0 0 0 0 0 0 0 -3.74100   0.000   0.000     38.00   0.31    1.008
SFAC  N   0 0 0 0 0 0 0 0  9.36000   0.000   0.000     1.90    0.70   14.007
SFAC  O   0 0 0 0 0 0 0 0  5.80500   0.000   0.000     0.0019  0.66   15.999
SFAC  S   0 0 0 0 0 0 0 0  2.84700   0.000   0.000     0.52    1.02   32.065
UNIT 48 36 12 8 4

L.S. 5
BOND $H
REM Instructions for hydrogen bonds with esds
HTAB N1 O2
EQIV $1 -x, -y+1, -z+1
HTAB N1 N2_$1
HTAB C2 S
EQIV $2 -x+1/2, y+1/2, -z+3/2
HTAB C11 O1_$2
EQIV $3 -x-1/2, y+1/2, -z+1/2
HTAB C11 N2_$3
HTAB C11 O1_$2
EQIV $4 -x, -y+2, -z+1
HTAB C11 S_$4
HTAB C11 N2_$3

CONF C1 N1 C7 S
CONF C2 C1 N1 C7
MPLA C1 C2 C3 C4 C5 C6
MPLA S C7 C8 C9 C10

ACTA
MERG 0
FMAP -2
PLAN 10
temp -123

sadi 0.007 C11 H111 c11 h112 c11 h113
sadi 0.007 h111 h112 h111 h113 h112 h113

sump 1 0.01 1.0 2 1.0 3 1.0 4

omit    -1   2  -3
omit     0   4  -1
omit     4   3  -6
omit    -3  -2   0
omit     8   0  -8
omit     0  -2  -4
omit    -2  -4  -2
omit    -1  -2   0
omit     1  -4  -1
omit    -2   7  -2
omit    -4  -8   3
omit     7   6 -12

WGHT    0.100000
EXTI    0.006002
BASF   0.93659   0.74900   0.78246   0.82894
FVAR       0.33996   0.39377   0.25327   0.35668   0.03227   0.04087   0.04411
S     5    0.068174    0.837165    0.536289    11.00000    0.02719    0.01575 =
         0.01535    0.00001    0.00524   -0.00032
O1    4    0.171159    0.539731    0.987300    11.00000    0.03216    0.04105 =
         0.02814    0.01283    0.00159    0.00853
O2    4    0.068684    0.512038    0.800061    11.00000    0.07780    0.02248 =
         0.02657    0.00587    0.01633    0.01545
N1    3   -0.007538    0.671632    0.660402    11.00000    0.03569    0.01518 =
         0.01675    0.00028    0.00842    0.00347
N2    3   -0.224785    0.499121    0.424203    11.00000    0.02925    0.01903 =
         0.03567   -0.00173    0.00051   -0.00486
N3    3    0.091157    0.567296    0.888341    11.00000    0.02556    0.02682 =
         0.02406    0.00773    0.00944    0.00453
C1    1   -0.032615    0.715598    0.762476    11.00000    0.01849    0.01607 =
         0.01591   -0.00054    0.00428   -0.00138
C2    1   -0.109800    0.811848    0.759933    11.00000    0.02546    0.01789 =
         0.02020   -0.00154    0.00911    0.00059
C3    1   -0.131986    0.857391    0.862139    11.00000    0.02986    0.02305 =
         0.02931   -0.00602    0.01465    0.00033
C4    1   -0.078718    0.809147    0.971804    11.00000    0.03445    0.03328 =
         0.02101   -0.00860    0.01297   -0.00257
C5    1   -0.004732    0.714256    0.977253    11.00000    0.02381    0.03294 =
         0.01820   -0.00020    0.00678   -0.00107
C6    1    0.016964    0.667932    0.874461    11.00000    0.01713    0.02268 =
         0.01525   -0.00013    0.00515   -0.00216
C7    1   -0.020475    0.719785    0.553050    11.00000    0.02127    0.01401 =
         0.01608   -0.00078    0.00428    0.00141
C8    1   -0.085804    0.676183    0.443323    11.00000    0.01882    0.01460 =
         0.01637   -0.00145    0.00311    0.00126
C9    1   -0.066171    0.738267    0.347195    11.00000    0.02085    0.01961 =
         0.01273    0.00112    0.00088    0.00170
C10   1    0.012236    0.828199    0.383836    11.00000    0.01988    0.01682 =
         0.01701    0.00194    0.00274    0.00099
C11   1    0.048966    0.913687    0.309806    11.00000    0.02752    0.02529 =
         0.01924    0.00794    0.00085   -0.00304
C12   1   -0.163959    0.579052    0.432079    11.00000    0.02095    0.01573 =
         0.02247   -0.00175    0.00163   -0.00079
H1    2    0.030396    0.598740    0.666094    11.00000    0.06982    0.02197 =
         0.03659    0.00397    0.01654    0.01049
H2    2   -0.155301    0.849721    0.675030    11.00000    0.05130    0.03464 =
         0.03240    0.00293    0.01286    0.01209
H3    2   -0.195051    0.930945    0.855732    11.00000    0.06943    0.03350 =
         0.05596   -0.00578    0.03305    0.01165
H4    2   -0.101879    0.845060    1.049771    11.00000    0.07535    0.05768 =
         0.03532   -0.01177    0.02547    0.00879
H5    2    0.033280    0.672557    1.060754    11.00000    0.05265    0.06008 =
         0.02498    0.00714    0.01036    0.00789
H9    2   -0.111284    0.715923    0.255614    11.00000    0.04671    0.04557 =
         0.02550   -0.00538   -0.00310   -0.00704
rem
rem rotationally disordered methyl group
part 1
H111  2   -0.040954    0.977290    0.310695    21.00000   51.00000
H112  2    0.185504    0.942272    0.343029    21.00000   51.00000
H113  2    0.034364    0.890165    0.217797    21.00000   51.00000
part 2
H111  2   -0.069123    0.952640    0.259986    31.00000   61.00000
H112  2    0.142632    0.969765    0.358495    31.00000   61.00000
H113  2    0.113805    0.880588    0.242778    31.00000   61.00000
part 3
H111  2    0.016740    0.985593    0.348589    41.00000   71.00000
H112  2    0.186034    0.918109    0.304446    41.00000   71.00000
H113  2   -0.038931    0.908734    0.221304    41.00000   71.00000
part 0

hklf 2

REM  ROY-OP orange at 150K SXD 3D integration
REM R1 =  0.0673 for    7180 Fo > 4sig(Fo)  and  0.0673 for all    7180 data
REM    255 parameters refined using     73 restraints

END

WGHT      0.1052     12.6384

REM Highest difference peak  1.206,  deepest hole -1.271,  1-sigma level  0.257
Q1    1   0.0508  0.5884  0.8766  11.00000  0.05   -1.27
Q2    1  -0.0199  0.6518  0.9483  11.00000  0.05   -1.22
Q3    1  -0.0722  0.9198  0.2375  11.00000  0.05   -1.18
Q4    1  -0.1710  0.8519  0.9250  11.00000  0.05   -1.15
Q5    1  -0.0559  0.5904  1.1214  11.00000  0.05   -1.12
Q6    1  -0.3669  0.5190  0.4650  11.00000  0.05    1.10
Q7    1   0.2174  0.9219  0.2885  11.00000  0.05    1.09
Q8    1   0.0926  0.9834  0.3853  11.00000  0.05   -1.07
Q9    1  -0.0160  0.9383  0.1920  11.00000  0.05    1.06
Q10   1   0.2311  0.9223  0.3704  11.00000  0.05   -1.03
;
_shelx_res_checksum              72446
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ROY_OP_100K
_database_code_depnum_ccdc_archive 'CCDC 1878592'
_audit_update_record             
;
2018-11-13 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_LABEL01_ROY_OP_100K         
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_LABEL01_ROY_OP_100K_2       
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_LABEL01_ROY_OP_100K_3       
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_LABEL01_ROY_OP_100K_4       
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_LABEL01_ROY_OP_100K_5       
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_LABEL01_ROY_OP_100K_6       
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_LABEL01_ROY_OP_100K_7       
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_LABEL01_ROY_OP_100K_8       
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_LABEL01_ROY_OP_100K_9       
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_DIFMN02_ROY_OP_100K         
;
PROBLEM: he minimum difference density is < -0.1*zmax*0.75="" _refine_diff_density_min="" given="-1.271" test="" value="-1.200"><a href='javascript:makeHelpWindow("DIFMN_03.html")'>DIFMN03_ALERT_1_C</a> The minimum difference density is < -0.1*zmax*0.75="" the="" relevant="" atom="" site="" should="" be="" identified.=""><a href='javascript:makeHelpWindow("DIFMX_02.html")'>DIFMX02_ALERT_1_C</a> The maximum difference density is > 0.1*ZMAX*0.75
RESPONSE: This alert relates to residual electron density, however our difference maps are calculated from nuclear scattering density. Residual positive and negative densities have approximately the same magnitude. Furthermore, the molecular structure is known and any ambiguities in atomic positioning are going to be most significant around the rotationally disordered methyl group
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
_chemical_name_common            ROY-OP
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H9 N3 O2 S'
_chemical_formula_weight         259.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_length_neutron
_atom_type_scat_source
C C 0.0000 0.0000 6.646 'Neutron Data Booklet Table 1.1-8'
H H 0.0000 0.0000 -3.739 'Neutron Data Booklet Table 1.1-8'
N N 0.0000 0.0000 9.360 'Neutron Data Booklet Table 1.1-8'
O O 0.0000 0.0000 5.805 'Neutron Data Booklet Table 1.1-8'
S S 0.0000 0.0000 2.847 'Neutron Data Booklet Table 1.1-8'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   7.713(2)
_cell_length_b                   13.271(3)
_cell_length_c                   11.611(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.004(19)
_cell_angle_gamma                90
_cell_volume                     1153.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    550
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prismatic
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_F_000             355
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          4
_exptl_crystal_size_mid          3
_exptl_crystal_size_min          2
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)

_diffrn_radiation_type           neutron
_diffrn_radiation_details        
;
 white beam
;
_diffrn_source                   'spallation source'
_diffrn_measurement_device_type  'time-of-flight diffractometer'
_diffrn_measurement_method       'time-of-flight profile data'
_diffrn-detector                 'scintillation counters'
_diffrn_detector_area_resol_mean 0.33
_diffrn_detector_details         
;
Array of eleven flat square fiber-optically coupled scintillator PSD 
with 64 x 64 pixels and active area of 192 x 192 mm each
(resolution: 0.33 by 0.33 pixels/mm)
;
_diffrn_reflns_number            8243
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         8.479
_diffrn_reflns_theta_max         86.304
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.154
_diffrn_measured_fraction_theta_full 0.746
_diffrn_reflns_Laue_measured_fraction_max 0.154
_diffrn_reflns_Laue_measured_fraction_full 0.746
_diffrn_reflns_point_group_measured_fraction_max 0.154
_diffrn_reflns_point_group_measured_fraction_full 0.746
_reflns_number_total             8243
_reflns_number_gt                8243
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       SECI
_computing_cell_refinement       'SXD2001 (Gutmann, 2005)'
_computing_data_reduction        'SXD2001 (Gutmann, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury 3.6, (CCDC 2015)'
_computing_publication_material  'Mercury 3.6, (CCDC 2015)'

_refine_special_details          
;
 Refinement of F² against ALL unmerged Laue reflections.
 R1=0.0624 for 3223 unique reflections after merging for Fourier.
 
 CheckCIF alerts
 
PROBLEM: An _atom_site_label occurs more than once in the atom list.
PROBLEM: Duplicate Atomic Label on INPUT ................       H111 Note  
PROBLEM: Angle   Calc    115.2(9), Rep    111.8(6), Dev..       3.78 Sigma 
PROBLEM: H...A   Calc     3.54(2), Rep    2.846(9), Dev..      34.70 Sigma 
PROBLEM: D-H..A  Calc   104.4(13), Rep   174.7(13), Dev..      54.08 Sigma 
PROBLEM: Bond    Calc   1.084(17), Rep    1.105(7), Dev..       1.24 Sigma 
PROBLEM: D-H     Calc   1.084(17), Rep    1.105(7), Dev..       1.24 Sigma 

RESPONSE: The above errors all relate to geometry involving the H atoms on a
rotationally-disordered methyl group. The atom labelling of these atoms across
different disordered parts appears to give the atoms the same label, leading
to these geometric errors. Platon has not interpreted the disorder grouping 
information given below by _atom_site_disorder_assembly and 
_atom_site_disorder_group.


PROBLEM: The minimum difference density is < -0.1*ZMAX*0.75
PROBLEM: The maximum difference density is > 0.1*ZMAX*0.75

RESPONSE: These alerts relate to residual electron density, however
our difference maps are calculated from nuclear scattering density. Residual
positive and negative densities have approximately the same magnitude.
Furthermore, the molecular structure is known and any ambiguities in atomic
positioning are going to be most significant around the rotationally 
disordered methyl group.


PROBLEM: Missing _cell_measurement_theta_min Value ......     Please Do ! 
PROBLEM: Missing _cell_measurement_theta_max Value ......     Please Do ! 

RESPONSE: Not applicable - data were measured by the time-of-flight method
using a white beam.


PROBLEM: No Datum for _diffrn_reflns_av_R_equivalents ...     Please Do ! 

RESPONSE: Not applicable - statistics on equivalent reflections are not available
as they are measured at different wavelengths. A statement regarding Rmerging 
statistics is given at the start of this section.


PROBLEM: No (Interpretable) Reflections Found in FCF ....     Please Check

RESPONSE: No action taken. The hkl reflection list is provided at the end of this CIF.


PROBLEM: Short Inter XH3 .. XHn     H4       ..H113     .       2.10 Ang.  

RESPONSE: No action taken. This is short, but not impossibly so - it lies toward
the lower end of a histogram of H...H contact distances in the CSD. This error
relates to a disordered hydrogen atom on the methyl group.
;


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0064(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8243
_refine_ls_number_parameters     255
_refine_ls_number_restraints     73
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0701
_refine_ls_wR_factor_ref         0.1881
_refine_ls_wR_factor_gt          0.1881
_refine_ls_goodness_of_fit_ref   1.549
_refine_ls_restrained_S_all      1.563
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.0678(5) 0.8376(3) 0.5367(5) 0.0137(10) Uani 1 1 d . . . . .
O1 O 0.1715(3) 0.5392(2) 0.9865(3) 0.0263(7) Uani 1 1 d . . . . .
O2 O 0.0676(4) 0.5117(2) 0.7995(4) 0.0313(7) Uani 1 1 d . . . . .
N1 N -0.00787(17) 0.67184(10) 0.66021(17) 0.0166(3) Uani 1 1 d . . . . .
N2 N -0.22509(16) 0.49885(10) 0.42365(19) 0.0221(4) Uani 1 1 d . . . . .
N3 N 0.09060(16) 0.56707(11) 0.88803(18) 0.0188(4) Uani 1 1 d . . . . .
C1 C -0.03320(19) 0.71573(13) 0.7619(2) 0.0129(4) Uani 1 1 d . . . . .
C2 C -0.1101(2) 0.81238(14) 0.7599(2) 0.0152(5) Uani 1 1 d . . . . .
C3 C -0.1323(2) 0.85768(15) 0.8620(3) 0.0199(5) Uani 1 1 d . . . . .
C4 C -0.0789(2) 0.80967(17) 0.9719(3) 0.0219(5) Uani 1 1 d . . . . .
C5 C -0.0051(2) 0.71433(17) 0.9772(2) 0.0193(5) Uani 1 1 d . . . . .
C6 C 0.01663(19) 0.66786(14) 0.8743(2) 0.0139(4) Uani 1 1 d . . . . .
C7 C -0.02035(19) 0.72010(13) 0.5526(2) 0.0131(4) Uani 1 1 d . . . . .
C8 C -0.08532(19) 0.67627(13) 0.4429(2) 0.0124(4) Uani 1 1 d . . . . .
C9 C -0.06573(19) 0.73871(14) 0.3468(2) 0.0135(4) Uani 1 1 d . . . . .
C10 C 0.01286(19) 0.82897(14) 0.3837(2) 0.0138(4) Uani 1 1 d . . . . .
C11 C 0.0492(2) 0.91465(15) 0.3096(2) 0.0185(5) Uani 1 1 d D . . . .
C12 C -0.16367(19) 0.57893(13) 0.4317(2) 0.0152(4) Uani 1 1 d . . . . .
H1 H 0.0301(7) 0.5986(3) 0.6655(6) 0.0353(13) Uani 1 1 d . . . . .
H2 H -0.1554(6) 0.8502(4) 0.6752(6) 0.0344(13) Uani 1 1 d . . . . .
H3 H -0.1944(7) 0.9318(4) 0.8570(7) 0.0417(15) Uani 1 1 d . . . . .
H4 H -0.1027(8) 0.8458(5) 1.0496(7) 0.0416(14) Uani 1 1 d . . . . .
H5 H 0.0335(7) 0.6725(4) 1.0615(6) 0.0388(13) Uani 1 1 d . . . . .
H9 H -0.1112(6) 0.7168(4) 0.2543(6) 0.0339(12) Uani 1 1 d . . . . .
H111 H -0.0400(13) 0.9788(7) 0.3117(14) 0.025(2) Uiso 0.40(2) 1 d D U P A 1
H112 H 0.1870(9) 0.9422(9) 0.3401(12) 0.025(2) Uiso 0.40(2) 1 d D U P A 1
H113 H 0.0300(17) 0.8916(8) 0.2171(8) 0.025(2) Uiso 0.40(2) 1 d D U P A 1
H111 H -0.0669(15) 0.9588(14) 0.267(2) 0.036(4) Uiso 0.25(2) 1 d D U P B 2
H112 H 0.154(2) 0.9650(14) 0.3576(17) 0.036(4) Uiso 0.25(2) 1 d D U P B 2
H113 H 0.101(3) 0.8799(13) 0.2378(16) 0.036(4) Uiso 0.25(2) 1 d D U P B 2
H111 H 0.016(2) 0.9867(8) 0.3470(15) 0.038(3) Uiso 0.35(2) 1 d D U P C 3
H112 H 0.1869(10) 0.9177(12) 0.3058(16) 0.038(3) Uiso 0.35(2) 1 d D U P C 3
H113 H -0.0379(19) 0.9084(11) 0.2211(10) 0.038(3) Uiso 0.35(2) 1 d D U P C 3

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
S 0.0186(13) 0.0115(16) 0.012(3) -0.0016(18) 0.0054(15) -0.0002(11)
O1 0.0224(8) 0.0309(13) 0.023(2) 0.0107(14) 0.0011(9) 0.0059(8)
O2 0.0567(15) 0.0169(11) 0.023(2) 0.0058(13) 0.0138(13) 0.0105(10)
N1 0.0256(5) 0.0113(5) 0.0138(10) 0.0003(6) 0.0064(5) 0.0024(4)
N2 0.0213(5) 0.0135(5) 0.0286(12) -0.0017(7) 0.0006(5) -0.0032(4)
N3 0.0181(4) 0.0199(6) 0.0198(11) 0.0053(7) 0.0074(5) 0.0035(4)
C1 0.0140(5) 0.0121(7) 0.0129(13) -0.0009(8) 0.0039(6) -0.0013(4)
C2 0.0184(6) 0.0119(7) 0.0168(14) -0.0013(8) 0.0073(7) 0.0009(5)
C3 0.0227(7) 0.0169(8) 0.0232(16) -0.0048(10) 0.0114(8) -0.0002(5)
C4 0.0250(7) 0.0242(10) 0.0185(16) -0.0051(10) 0.0094(8) -0.0019(6)
C5 0.0173(6) 0.0267(10) 0.0142(15) -0.0004(10) 0.0048(7) -0.0004(6)
C6 0.0128(5) 0.0160(7) 0.0138(13) 0.0000(8) 0.0049(6) -0.0020(4)
C7 0.0162(5) 0.0104(7) 0.0127(13) -0.0014(8) 0.0038(6) 0.0008(4)
C8 0.0136(5) 0.0106(6) 0.0125(12) -0.0009(8) 0.0023(6) 0.0009(4)
C9 0.0147(5) 0.0139(7) 0.0104(13) -0.0003(8) 0.0002(6) 0.0006(5)
C10 0.0143(5) 0.0131(7) 0.0137(13) 0.0016(8) 0.0024(6) 0.0005(4)
C11 0.0196(6) 0.0187(9) 0.0153(15) 0.0057(9) 0.0004(7) -0.0024(5)
C12 0.0145(5) 0.0121(7) 0.0181(13) -0.0011(8) 0.0021(6) -0.0006(4)
H1 0.061(3) 0.0192(18) 0.028(4) 0.002(2) 0.015(2) 0.0103(17)
H2 0.043(2) 0.029(2) 0.032(4) 0.005(2) 0.012(2) 0.0098(16)
H3 0.056(3) 0.030(2) 0.046(5) -0.006(3) 0.027(3) 0.0108(18)
H4 0.056(3) 0.046(3) 0.026(4) -0.008(3) 0.017(2) 0.006(2)
H5 0.047(2) 0.045(3) 0.025(4) 0.005(3) 0.008(2) 0.0059(19)
H9 0.0415(19) 0.037(2) 0.019(4) -0.004(2) -0.0011(19) -0.0053(17)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S C10 1.727(7) . ?
S C7 1.729(4) . ?
O1 N3 1.220(4) . ?
O2 N3 1.240(4) . ?
N1 C1 1.373(3) . ?
N1 C7 1.386(3) . ?
N1 H1 1.013(5) . ?
N2 C12 1.158(2) . ?
N3 C6 1.448(2) . ?
C1 C2 1.411(2) . ?
C1 C6 1.418(3) . ?
C2 C3 1.377(4) . ?
C2 H2 1.084(7) . ?
C3 C4 1.397(4) . ?
C3 H3 1.089(5) . ?
C4 C5 1.382(3) . ?
C4 H4 1.076(8) . ?
C5 C6 1.390(3) . ?
C5 H5 1.102(8) . ?
C7 C8 1.379(3) . ?
C8 C12 1.419(2) . ?
C8 C9 1.427(3) . ?
C9 C10 1.364(3) . ?
C9 H9 1.085(7) . ?
C10 C11 1.493(3) . ?
C11 H111 1.098(6) . ?
C11 H112 1.098(6) . ?
C11 H113 1.092(8) . ?
C11 H111 1.085(8) . ?
C11 H112 1.090(8) . ?
C11 H113 1.110(8) . ?
C11 H111 1.105(7) . ?
C11 H112 1.075(7) . ?
C11 H113 1.087(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 S C7 92.6(2) . . ?
C1 N1 C7 125.88(15) . . ?
C1 N1 H1 117.0(4) . . ?
C7 N1 H1 117.0(4) . . ?
O1 N3 O2 122.4(2) . . ?
O1 N3 C6 118.8(2) . . ?
O2 N3 C6 118.8(2) . . ?
N1 C1 C2 121.2(2) . . ?
N1 C1 C6 122.57(15) . . ?
C2 C1 C6 116.2(2) . . ?
C3 C2 C1 121.5(2) . . ?
C3 C2 H2 119.9(3) . . ?
C1 C2 H2 118.6(4) . . ?
C2 C3 C4 121.15(19) . . ?
C2 C3 H3 119.6(5) . . ?
C4 C3 H3 119.3(5) . . ?
C5 C4 C3 119.0(2) . . ?
C5 C4 H4 121.6(5) . . ?
C3 C4 H4 119.3(4) . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 121.3(4) . . ?
C6 C5 H5 118.5(4) . . ?
C5 C6 C1 121.98(18) . . ?
C5 C6 N3 116.2(2) . . ?
C1 C6 N3 121.8(2) . . ?
C8 C7 N1 124.59(16) . . ?
C8 C7 S 110.2(3) . . ?
N1 C7 S 124.7(2) . . ?
C7 C8 C12 121.4(2) . . ?
C7 C8 C9 113.19(16) . . ?
C12 C8 C9 125.5(2) . . ?
C10 C9 C8 112.8(2) . . ?
C10 C9 H9 124.0(4) . . ?
C8 C9 H9 123.2(3) . . ?
C9 C10 C11 128.2(2) . . ?
C9 C10 S 111.2(2) . . ?
C11 C10 S 120.6(2) . . ?
C10 C11 H111 111.8(6) . . ?
C10 C11 H112 111.7(7) . . ?
H111 C11 H112 107.3(6) . . ?
C10 C11 H113 110.8(6) . . ?
H111 C11 H113 107.6(7) . . ?
H112 C11 H113 107.5(7) . . ?
C10 C11 H111 115.2(11) . . ?
C10 C11 H112 113.0(12) . . ?
H111 C11 H112 109.2(9) . . ?
C10 C11 H113 105.6(11) . . ?
H111 C11 H113 106.8(9) . . ?
H112 C11 H113 106.4(9) . . ?
C10 C11 H111 109.8(9) . . ?
C10 C11 H112 112.2(9) . . ?
H111 C11 H112 108.1(7) . . ?
C10 C11 H113 109.2(8) . . ?
H111 C11 H113 106.7(8) . . ?
H112 C11 H113 110.8(9) . . ?
N2 C12 C8 178.9(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C7 S 43.5(3) . . . . ?
C2 C1 N1 C7 12.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 1.013(5) 1.902(7) 2.649(4) 128.0(5) .
N1 H1 N2 1.013(5) 2.400(6) 3.187(2) 133.9(5) 3_566
C2 H2 S 1.084(7) 2.630(8) 3.230(6) 114.2(3) .
C11 H112 O1 1.090(8) 2.210(10) 3.242(3) 157.0(17) 2_556
C11 H111 N2 1.085(8) 2.456(17) 3.399(3) 144.7(18) 2_455
C11 H112 O1 1.090(8) 2.210(10) 3.242(3) 157.0(17) 2_556
C11 H111 S 1.105(7) 2.846(9) 3.948(5) 174.7(13) 3_576
C11 H111 N2 1.085(8) 2.456(17) 3.399(3) 144.7(18) 2_455

_refine_diff_density_max         1.744
_refine_diff_density_min         -1.443
_refine_diff_density_rms         0.322

_shelx_res_file                  
;

    roy100_3d.res created by SHELXL-2014/7


TITL ROY-OP orange at 100K SXD 3D integration
CELL 0.7   7.7129   13.2714   11.6113  90.0000  104.004   90.0000
ZERR  4.0  0.0024    0.0034    0.0036    0.000    0.019    0.000
LATT  1
SYMM 1/2-x,1/2+y,1/2-z
SFAC  C   0 0 0 0 0 0 0 0  6.64800   0.000   0.000     0.035   0.76   12.010
SFAC  H   0 0 0 0 0 0 0 0 -3.74100   0.000   0.000     38.00   0.31    1.008
SFAC  N   0 0 0 0 0 0 0 0  9.36000   0.000   0.000     1.90    0.70   14.007
SFAC  O   0 0 0 0 0 0 0 0  5.80500   0.000   0.000     0.0019  0.66   15.999
SFAC  S   0 0 0 0 0 0 0 0  2.84700   0.000   0.000     0.52    1.02   32.065
UNIT 48 36 12 8 4

L.S. 5
BOND $H
REM Instructions hydrogen bonds with esds
HTAB N1 O2
EQIV $1 -x, -y+1, -z+1
HTAB N1 N2_$1
HTAB C2 S
EQIV $2 -x+1/2, y+1/2, -z+3/2
HTAB C11 O1_$2
EQIV $3 -x-1/2, y+1/2, -z+1/2
HTAB C11 N2_$3
HTAB C11 O1_$2
EQIV $4 -x, -y+2, -z+1
HTAB C11 S_$4
HTAB C11 N2_$3
CONF C1 N1 C7 S
CONF C2 C1 N1 C7
MPLA C1 C2 C3 C4 C5 C6
MPLA S C7 C8 C9 C10
ACTA
MERG 0
FMAP -2
PLAN 10
temp -173

sadi 0.007 C11 H111 c11 h112 c11 h113
sadi 0.007 h111 h112 h111 h113 h112 h113

sump 1 0.01 1.0 2 1.0 3 1.0 4

omit     0 -12   0
omit     0   4  -1
omit     0  -2  -4
omit     7  -1  -3
omit    -1  -2   0
omit    -2  -6  -1
omit    10  -1  -9
omit    -5   6   1
omit     2   2   2
omit    -2   7  -2
omit     4  -7  -3
omit    -4  -2   1

WGHT    0.100000
EXTI    0.006359
BASF   0.94200   0.75034   1.01009   0.80610
FVAR       0.34531   0.40183   0.24972   0.34898   0.02463   0.03590   0.03843
S     5    0.067791    0.837615    0.536653    11.00000    0.01857    0.01148 =
         0.01197   -0.00159    0.00536   -0.00024
O1    4    0.171526    0.539220    0.986546    11.00000    0.02241    0.03090 =
         0.02326    0.01074    0.00113    0.00586
O2    4    0.067588    0.511745    0.799544    11.00000    0.05667    0.01694 =
         0.02257    0.00582    0.01383    0.01050
N1    3   -0.007867    0.671842    0.660207    11.00000    0.02556    0.01133 =
         0.01376    0.00031    0.00636    0.00244
N2    3   -0.225087    0.498845    0.423646    11.00000    0.02133    0.01348 =
         0.02861   -0.00165    0.00064   -0.00318
N3    3    0.090597    0.567074    0.888032    11.00000    0.01811    0.01994 =
         0.01977    0.00531    0.00744    0.00353
C1    1   -0.033200    0.715734    0.761935    11.00000    0.01397    0.01206 =
         0.01290   -0.00094    0.00390   -0.00126
C2    1   -0.110093    0.812377    0.759868    11.00000    0.01845    0.01193 =
         0.01682   -0.00125    0.00734    0.00092
C3    1   -0.132283    0.857681    0.861984    11.00000    0.02266    0.01686 =
         0.02316   -0.00479    0.01141   -0.00020
C4    1   -0.078865    0.809666    0.971912    11.00000    0.02501    0.02425 =
         0.01847   -0.00507    0.00945   -0.00193
C5    1   -0.005113    0.714334    0.977156    11.00000    0.01733    0.02672 =
         0.01420   -0.00039    0.00478   -0.00042
C6    1    0.016629    0.667863    0.874316    11.00000    0.01277    0.01601 =
         0.01377   -0.00001    0.00489   -0.00201
C7    1   -0.020348    0.720098    0.552612    11.00000    0.01623    0.01039 =
         0.01270   -0.00141    0.00379    0.00084
C8    1   -0.085323    0.676265    0.442923    11.00000    0.01358    0.01063 =
         0.01253   -0.00090    0.00233    0.00091
C9    1   -0.065732    0.738708    0.346771    11.00000    0.01473    0.01389 =
         0.01040   -0.00031    0.00018    0.00060
C10   1    0.012859    0.828973    0.383738    11.00000    0.01429    0.01305 =
         0.01366    0.00164    0.00236    0.00053
C11   1    0.049165    0.914648    0.309607    11.00000    0.01963    0.01868 =
         0.01527    0.00565    0.00037   -0.00238
C12   1   -0.163675    0.578934    0.431687    11.00000    0.01445    0.01207 =
         0.01806   -0.00110    0.00208   -0.00061
H1    2    0.030065    0.598582    0.665517    11.00000    0.06140    0.01918 =
         0.02767    0.00210    0.01513    0.01034
H2    2   -0.155356    0.850214    0.675188    11.00000    0.04331    0.02864 =
         0.03245    0.00455    0.01168    0.00984
H3    2   -0.194361    0.931787    0.857013    11.00000    0.05645    0.02955 =
         0.04628   -0.00590    0.02651    0.01077
H4    2   -0.102697    0.845847    1.049567    11.00000    0.05620    0.04615 =
         0.02607   -0.00834    0.01701    0.00574
H5    2    0.033547    0.672522    1.061495    11.00000    0.04658    0.04467 =
         0.02487    0.00460    0.00815    0.00588
H9    2   -0.111226    0.716831    0.254334    11.00000    0.04148    0.03664 =
         0.01915   -0.00449   -0.00110   -0.00534
rem
rem rotationally disordered methyl group
part 1
H111  2   -0.040025    0.978764    0.311695    21.00000   51.00000
H112  2    0.186964    0.942193    0.340072    21.00000   51.00000
H113  2    0.030033    0.891614    0.217114    21.00000   51.00000
part 2
H111  2   -0.066915    0.958836    0.266872    31.00000   61.00000
H112  2    0.153573    0.965011    0.357555    31.00000   61.00000
H113  2    0.101252    0.879883    0.237801    31.00000   61.00000
part 3
H111  2    0.015828    0.986656    0.346979    41.00000   71.00000
H112  2    0.186900    0.917682    0.305776    41.00000   71.00000
H113  2   -0.037895    0.908442    0.221060    41.00000   71.00000
part 0

hklf 2

REM  ROY-OP orange at 100K SXD 3D integration
REM R1 =  0.0701 for    8243 Fo > 4sig(Fo)  and  0.0701 for all    8243 data
REM    255 parameters refined using     73 restraints

END

WGHT      0.1043     18.3637

REM Highest difference peak  1.744,  deepest hole -1.443,  1-sigma level  0.322
Q1    1  -0.0077  0.9639  0.3269  11.00000  0.05    1.71
Q2    1  -0.0152  0.6770  0.9514  11.00000  0.05   -1.44
Q3    1  -0.0467  0.7411  0.4358  11.00000  0.05    1.40
Q4    1   0.1096  0.7560  0.7778  11.00000  0.05   -1.39
Q5    1  -0.1660  0.8522  0.9274  11.00000  0.05   -1.37
Q6    1  -0.2237  0.6071  0.3900  11.00000  0.05   -1.36
Q7    1  -0.1125  0.9216  0.3620  11.00000  0.05    1.31
Q8    1   0.0323  1.0100  0.3351  11.00000  0.05    1.28
Q9    1  -0.0677  1.0001  0.2964  11.00000  0.05    1.27
Q10   1  -0.2001  0.9544  0.2804  11.00000  0.05    1.26
;
_shelx_res_checksum              34889
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ROY_OP_40K
_database_code_depnum_ccdc_archive 'CCDC 1878594'
_audit_update_record             
;
2018-11-13 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_DIFMN02_ROY_OP_40K          
;
PROBLEM: The minimum difference density is < -0.1*zmax*0.75="" _refine_diff_density_min="" given="-1.271" test="" value="-1.200"><a href='javascript:makeHelpWindow("DIFMN_03.html")'>DIFMN03_ALERT_1_C</a> The minimum difference density is < -0.1*zmax*0.75="" the="" relevant="" atom="" site="" should="" be="" identified.=""><a href='javascript:makeHelpWindow("DIFMX_02.html")'>DIFMX02_ALERT_1_C</a> The maximum difference density is > 0.1*ZMAX*0.75
RESPONSE: These alerts relate to residual electron density, however our difference maps are calculated from nuclear scattering density. Residual positive and negative densities have approximately the same magnitude. Furthermore, the molecular structure is known and any ambiguities in atomic positioning are going to be most significant around the rotationally disordered methyl group
;
_vrf_DIFMN03_ROY_OP_40K          
;
PROBLEM: The minimum difference density is < -0.1*zmax*0.75="" _refine_diff_density_min="" given="-1.271" test="" value="-1.200"><a href='javascript:makeHelpWindow("DIFMN_03.html")'>DIFMN03_ALERT_1_C</a> The minimum difference density is < -0.1*zmax*0.75="" the="" relevant="" atom="" site="" should="" be="" identified.=""><a href='javascript:makeHelpWindow("DIFMX_02.html")'>DIFMX02_ALERT_1_C</a> The maximum difference density is > 0.1*ZMAX*0.75
RESPONSE: These alerts relate to residual electron density, however our difference maps are calculated from nuclear scattering density. Residual positive and negative densities have approximately the same magnitude. Furthermore, the molecular structure is known and any ambiguities in atomic positioning are going to be most significant around the rotationally disordered methyl group
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
_chemical_name_common            ROY-OP
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H9 N3 O2 S'
_chemical_formula_weight         259.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_length_neutron
_atom_type_scat_source
C C 0.0000 0.0000 6.646 'Neutron Data Booklet Table 1.1-8'
H H 0.0000 0.0000 -3.739 'Neutron Data Booklet Table 1.1-8'
N N 0.0000 0.0000 9.360 'Neutron Data Booklet Table 1.1-8'
O O 0.0000 0.0000 5.805 'Neutron Data Booklet Table 1.1-8'
S S 0.0000 0.0000 2.847 'Neutron Data Booklet Table 1.1-8'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   7.651(2)
_cell_length_b                   13.243(3)
_cell_length_c                   11.624(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.118(19)
_cell_angle_gamma                90
_cell_volume                     1142.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    40(2)
_cell_measurement_reflns_used    550
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prismatic
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_F_000             355
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          4
_exptl_crystal_size_mid          3
_exptl_crystal_size_min          2
_exptl_absorpt_coefficient_mu    0.122
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      '40 - 293'
_diffrn_radiation_type           neutron
_diffrn_radiation_details        
;
 white beam
;
_diffrn_source                   'spallation source'
_diffrn_measurement_device_type  'time-of-flight diffractometer'
_diffrn_measurement_method       'time-of-flight profile data'
_diffrn-detector                 'scintillation counters'
_diffrn_detector_area_resol_mean 0.33
_diffrn_detector_details         
;
Array of eleven flat square fiber-optically coupled scintillator PSD 
with 64 x 64 pixels and active area of 192 x 192 mm each
(resolution: 0.33 by 0.33 pixels/mm)
;
_diffrn_reflns_number            9984
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         8.284
_diffrn_reflns_theta_max         86.766
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.153
_diffrn_measured_fraction_theta_full 0.740
_diffrn_reflns_Laue_measured_fraction_max 0.153
_diffrn_reflns_Laue_measured_fraction_full 0.740
_diffrn_reflns_point_group_measured_fraction_max 0.153
_diffrn_reflns_point_group_measured_fraction_full 0.740
_reflns_number_total             9984
_reflns_number_gt                9984
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       SECI
_computing_cell_refinement       'SXD2001 (Gutmann, 2005)'
_computing_data_reduction        'SXD2001 (Gutmann, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury 3.6, (CCDC 2015)'
_computing_publication_material  'Mercury 3.6, (CCDC 2015)'

_refine_special_details          
;Refinement of F² against ALL unmerged Laue reflections.

 R1=0.0619 for 4113 unique reflections after merging for Fourier.

 

 

 CheckCIF alerts



PROBLEM: The minimum difference density is < -0.1*ZMAX*0.75

PROBLEM: The maximum difference density is > 0.1*ZMAX*0.75



RESPONSE: These alerts relate to residual electron density, however

our difference maps are calculated from nuclear scattering density. Residual

positive and negative densities have approximately the same magnitude.

Furthermore, the molecular structure is known and any ambiguities in atomic

positioning are going to be most significant around the rotationally 

disordered methyl group.





PROBLEM: Missing _cell_measurement_theta_min Value ......     Please Do ! 

PROBLEM: Missing _cell_measurement_theta_max Value ......     Please Do ! 



RESPONSE: Not applicable - data were measured by the time-of-flight method

using a white beam.





PROBLEM: No Datum for _diffrn_reflns_av_R_equivalents ...     Please Do ! 



RESPONSE: Not applicable - statistics on equivalent reflections are not available

as they are measured at different wavelengths. A statement regarding Rmerging 

statistics is given at the start of this section.





PROBLEM: No (Interpretable) Reflections Found in FCF ....     Please Check



RESPONSE: No action taken. The hkl reflection list is provided at the end of this CIF.





PROBLEM: Short Inter XH3 .. XHn     H4       ..H113     .       2.08 Ang.  



RESPONSE: No action taken. This is short, but not impossibly so - it lies toward

the lower end of a histogram of H...H contact distances in the CSD. This error

relates to a disordered hydrogen atom on the methyl group.
;



_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0080(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         9984
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0690
_refine_ls_wR_factor_ref         0.1795
_refine_ls_wR_factor_gt          0.1795
_refine_ls_goodness_of_fit_ref   1.448
_refine_ls_restrained_S_all      1.448
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.0680(4) 0.8386(3) 0.5365(5) 0.0079(8) Uani 1 1 d . . . . .
O1 O 0.1719(2) 0.53910(16) 0.9856(3) 0.0150(5) Uani 1 1 d . . . . .
O2 O 0.0658(3) 0.51124(16) 0.7989(3) 0.0168(5) Uani 1 1 d . . . . .
N1 N -0.00865(13) 0.67224(8) 0.65939(15) 0.0100(3) Uani 1 1 d . . . . .
N2 N -0.22522(13) 0.49851(8) 0.42289(16) 0.0128(3) Uani 1 1 d . . . . .
N3 N 0.08990(12) 0.56690(8) 0.88692(15) 0.0103(3) Uani 1 1 d . . . . .
C1 C -0.03416(15) 0.71625(11) 0.76132(19) 0.0078(3) Uani 1 1 d . . . . .
C2 C -0.11144(17) 0.81312(11) 0.7590(2) 0.0091(4) Uani 1 1 d . . . . .
C3 C -0.13343(18) 0.85867(12) 0.8614(2) 0.0113(4) Uani 1 1 d . . . . .
C4 C -0.07998(19) 0.81029(13) 0.9712(2) 0.0122(4) Uani 1 1 d . . . . .
C5 C -0.00608(17) 0.71479(13) 0.9762(2) 0.0104(4) Uani 1 1 d . . . . .
C6 C 0.01566(16) 0.66807(11) 0.87311(19) 0.0086(3) Uani 1 1 d . . . . .
C7 C -0.02086(16) 0.72058(11) 0.5521(2) 0.0077(3) Uani 1 1 d . . . . .
C8 C -0.08559(16) 0.67652(11) 0.44212(19) 0.0069(3) Uani 1 1 d . . . . .
C9 C -0.06510(16) 0.73910(11) 0.3465(2) 0.0085(3) Uani 1 1 d . . . . .
C10 C 0.01326(16) 0.82977(11) 0.38341(19) 0.0080(3) Uani 1 1 d . . . . .
C11 C 0.04913(18) 0.91629(12) 0.3095(2) 0.0114(4) Uani 1 1 d . . . . .
C12 C -0.16370(16) 0.57888(11) 0.4303(2) 0.0094(4) Uani 1 1 d . . . . .
H1 H 0.0287(6) 0.5989(3) 0.6643(6) 0.0273(11) Uani 1 1 d . . . . .
H2 H -0.1568(5) 0.8514(3) 0.6732(5) 0.0244(10) Uani 1 1 d . . . . .
H3 H -0.1963(5) 0.9328(3) 0.8559(6) 0.0301(12) Uani 1 1 d . . . . .
H4 H -0.1032(6) 0.8465(4) 1.0495(6) 0.0295(11) Uani 1 1 d . . . . .
H5 H 0.0322(5) 0.6727(4) 1.0597(5) 0.0275(10) Uani 1 1 d . . . . .
H9 H -0.1101(5) 0.7170(3) 0.2543(5) 0.0251(10) Uani 1 1 d . . . . .
H111 H -0.0350(8) 0.9791(4) 0.3142(9) 0.060(2) Uani 1 1 d . . . . .
H112 H 0.1849(5) 0.9420(4) 0.3370(7) 0.0452(17) Uani 1 1 d . . . . .
H113 H 0.0212(13) 0.8957(6) 0.2194(8) 0.071(3) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S 0.0092(9) 0.0056(11) 0.009(2) -0.0009(14) 0.0026(11) -0.0004(7)
O1 0.0128(5) 0.0175(8) 0.0136(14) 0.0065(10) 0.0009(6) 0.0036(5)
O2 0.0276(8) 0.0096(8) 0.0141(16) 0.0019(9) 0.0067(8) 0.0050(6)
N1 0.0137(3) 0.0064(4) 0.0103(8) 0.0002(5) 0.0039(4) 0.0011(3)
N2 0.0110(3) 0.0077(4) 0.0183(9) -0.0005(5) 0.0007(4) -0.0024(3)
N3 0.0092(3) 0.0113(4) 0.0112(8) 0.0028(5) 0.0038(4) 0.0018(3)
C1 0.0075(4) 0.0067(5) 0.0100(11) 0.0002(6) 0.0033(5) -0.0008(3)
C2 0.0097(4) 0.0073(5) 0.0111(11) -0.0009(6) 0.0041(5) 0.0008(3)
C3 0.0115(4) 0.0095(6) 0.0144(12) -0.0022(7) 0.0061(5) 0.0002(4)
C4 0.0131(5) 0.0135(6) 0.0107(12) -0.0035(7) 0.0046(5) -0.0007(4)
C5 0.0101(4) 0.0142(7) 0.0073(11) -0.0007(7) 0.0026(5) -0.0002(4)
C6 0.0077(4) 0.0086(5) 0.0099(11) 0.0000(6) 0.0027(5) 0.0000(3)
C7 0.0090(4) 0.0059(5) 0.0081(10) -0.0004(6) 0.0020(5) 0.0001(3)
C8 0.0082(4) 0.0060(5) 0.0065(10) -0.0016(6) 0.0017(4) -0.0004(3)
C9 0.0086(4) 0.0077(5) 0.0088(11) -0.0001(6) 0.0009(5) -0.0001(3)
C10 0.0083(4) 0.0073(5) 0.0083(10) 0.0016(6) 0.0018(5) 0.0002(3)
C11 0.0115(5) 0.0100(6) 0.0119(12) 0.0018(7) 0.0013(5) -0.0011(4)
C12 0.0084(4) 0.0071(5) 0.0119(11) -0.0012(6) 0.0007(5) -0.0001(3)
H1 0.0420(19) 0.0148(15) 0.026(3) 0.0013(19) 0.0098(19) 0.0076(13)
H2 0.0308(15) 0.0235(17) 0.020(3) 0.0049(19) 0.0079(16) 0.0081(12)
H3 0.0369(17) 0.0191(17) 0.037(4) -0.004(2) 0.014(2) 0.0081(13)
H4 0.0378(18) 0.032(2) 0.021(3) -0.007(2) 0.0113(18) 0.0043(15)
H5 0.0330(16) 0.031(2) 0.018(3) 0.007(2) 0.0044(16) 0.0064(14)
H9 0.0339(16) 0.0254(18) 0.013(3) -0.0022(19) -0.0001(15) -0.0043(13)
H111 0.058(3) 0.037(3) 0.102(8) 0.038(4) 0.052(4) 0.026(2)
H112 0.0236(14) 0.052(3) 0.057(5) 0.024(3) 0.002(2) -0.0151(16)
H113 0.136(7) 0.051(4) 0.016(5) 0.008(4) -0.002(4) -0.050(4)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S C10 1.730(6) . ?
S C7 1.732(4) . ?
O1 N3 1.222(3) . ?
O2 N3 1.237(3) . ?
N1 C1 1.376(3) . ?
N1 C7 1.384(3) . ?
N1 H1 1.010(4) . ?
N2 C12 1.1585(18) . ?
N3 C6 1.4489(19) . ?
C1 C2 1.410(2) . ?
C1 C6 1.414(3) . ?
C2 C3 1.381(3) . ?
C2 H2 1.097(6) . ?
C3 C4 1.397(3) . ?
C3 H3 1.088(4) . ?
C4 C5 1.381(2) . ?
C4 H4 1.081(7) . ?
C5 C6 1.394(3) . ?
C5 H5 1.095(6) . ?
C7 C8 1.383(3) . ?
C8 C12 1.417(2) . ?
C8 C9 1.426(3) . ?
C9 C10 1.364(2) . ?
C9 H9 1.082(6) . ?
C10 C11 1.497(3) . ?
C11 H111 1.062(5) . ?
C11 H112 1.065(4) . ?
C11 H113 1.052(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 S C7 92.5(2) . . ?
C1 N1 C7 125.94(12) . . ?
C1 N1 H1 117.1(4) . . ?
C7 N1 H1 116.9(4) . . ?
O1 N3 O2 122.36(17) . . ?
O1 N3 C6 118.70(18) . . ?
O2 N3 C6 118.93(17) . . ?
N1 C1 C2 121.05(18) . . ?
N1 C1 C6 122.48(13) . . ?
C2 C1 C6 116.47(18) . . ?
C3 C2 C1 121.31(19) . . ?
C3 C2 H2 120.3(3) . . ?
C1 C2 H2 118.4(3) . . ?
C2 C3 C4 121.13(15) . . ?
C2 C3 H3 119.2(4) . . ?
C4 C3 H3 119.6(4) . . ?
C5 C4 C3 118.9(2) . . ?
C5 C4 H4 121.4(4) . . ?
C3 C4 H4 119.6(3) . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5 121.4(3) . . ?
C6 C5 H5 118.3(3) . . ?
C5 C6 C1 121.85(14) . . ?
C5 C6 N3 116.16(17) . . ?
C1 C6 N3 121.98(17) . . ?
C8 C7 N1 124.61(13) . . ?
C8 C7 S 110.2(2) . . ?
N1 C7 S 124.7(2) . . ?
C7 C8 C12 121.47(18) . . ?
C7 C8 C9 113.14(14) . . ?
C12 C8 C9 125.39(18) . . ?
C10 C9 C8 112.96(19) . . ?
C10 C9 H9 123.9(3) . . ?
C8 C9 H9 123.1(3) . . ?
C9 C10 C11 128.4(2) . . ?
C9 C10 S 111.17(19) . . ?
C11 C10 S 120.40(17) . . ?
C10 C11 H111 111.9(4) . . ?
C10 C11 H112 112.0(4) . . ?
H111 C11 H112 107.0(6) . . ?
C10 C11 H113 110.6(4) . . ?
H111 C11 H113 106.0(8) . . ?
H112 C11 H113 109.2(7) . . ?
N2 C12 C8 178.6(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C7 S 43.2(2) . . . . ?
C2 C1 N1 C7 12.80(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 1.010(4) 1.913(6) 2.655(3) 127.8(5) .
N1 H1 N2 1.010(4) 2.386(5) 3.1724(18) 134.0(4) 3_566
C2 H2 S 1.097(6) 2.617(7) 3.228(5) 114.4(3) .
C11 H112 O1 1.065(4) 2.451(8) 3.224(3) 128.6(6) 2_556

_refine_diff_density_max         2.230
_refine_diff_density_min         -2.081
_refine_diff_density_rms         0.414

_shelx_res_file                  
;

    roy40_3d.res created by SHELXL-2014/7


TITL ROY-OP orange at 60K SXD 3D prifile fitting integration
CELL 0.7 7.6508   13.2431   11.6243   90.0000  104.1183   90.0000
ZERR  4.0   0.0024    0.0033    0.0037    0.000     0.019   0.000
LATT  1
SYMM 1/2-x,1/2+y,1/2-z
SFAC  C   0 0 0 0 0 0 0 0  6.64800   0.000   0.000     0.035   0.76   12.010
SFAC  H   0 0 0 0 0 0 0 0 -3.74100   0.000   0.000     38.00   0.31    1.008
SFAC  N   0 0 0 0 0 0 0 0  9.36000   0.000   0.000     1.90    0.70   14.007
SFAC  O   0 0 0 0 0 0 0 0  5.80500   0.000   0.000     0.0019  0.66   15.999
SFAC  S   0 0 0 0 0 0 0 0  2.84700   0.000   0.000     0.52    1.02   32.065
UNIT 48 36 12 8 4

L.S. 5
BOND $H
REM Hydrogen bonds with esds
HTAB N1 O2
EQIV $1 -x, -y+1, -z+1
HTAB N1 N2_$1
HTAB C2 S
EQIV $2 -x+1/2, y+1/2, -z+3/2
HTAB C11 O1_$2
CONF C1 N1 C7 S
conf c2 c1 n1 c7
MPLA C1 C2 C3 C4 C5 C6
MPLA S C7 C8 C9 C10
ACTA
MERG 0
FMAP -2
PLAN 10
temp  -233

omit    -2 -11   0
omit     0  -2  -4
omit   -11   0   5
omit    12  -2  -1
omit     4  -7  -3
omit     2   2   2
omit    -5   6  -1
omit     2   2   0
omit     3   3   0
omit    -4  -2   1
omit     9   9  -3
omit    -1   6  -4
omit     3   4   4
omit    10 -10  -2
omit    -4   2   1
omit     1  -4  -1
omit     9  -6  -9

WGHT    0.100000
EXTI    0.007958
BASF   0.94585   0.73298   0.73408   0.78006
FVAR       0.35504
S     5    0.068033    0.838638    0.536504    11.00000    0.00919    0.00557 =
         0.00910   -0.00089    0.00262   -0.00038
O1    4    0.171876    0.539100    0.985558    11.00000    0.01275    0.01754 =
         0.01358    0.00650    0.00093    0.00358
O2    4    0.065787    0.511245    0.798930    11.00000    0.02761    0.00959 =
         0.01411    0.00188    0.00673    0.00498
N1    3   -0.008648    0.672240    0.659389    11.00000    0.01374    0.00638 =
         0.01028    0.00018    0.00395    0.00112
N2    3   -0.225216    0.498506    0.422888    11.00000    0.01096    0.00773 =
         0.01826   -0.00045    0.00068   -0.00245
N3    3    0.089905    0.566896    0.886917    11.00000    0.00923    0.01126 =
         0.01115    0.00285    0.00382    0.00176
C1    1   -0.034159    0.716251    0.761320    11.00000    0.00747    0.00667 =
         0.00997    0.00020    0.00331   -0.00079
C2    1   -0.111436    0.813118    0.759013    11.00000    0.00972    0.00729 =
         0.01114   -0.00085    0.00414    0.00077
C3    1   -0.133433    0.858672    0.861427    11.00000    0.01149    0.00952 =
         0.01438   -0.00222    0.00612    0.00016
C4    1   -0.079980    0.810285    0.971212    11.00000    0.01314    0.01352 =
         0.01073   -0.00346    0.00456   -0.00065
C5    1   -0.006084    0.714792    0.976192    11.00000    0.01011    0.01417 =
         0.00733   -0.00068    0.00262   -0.00019
C6    1    0.015657    0.668075    0.873106    11.00000    0.00771    0.00861 =
         0.00988   -0.00001    0.00269   -0.00004
C7    1   -0.020857    0.720582    0.552119    11.00000    0.00900    0.00589 =
         0.00814   -0.00039    0.00205    0.00015
C8    1   -0.085593    0.676521    0.442117    11.00000    0.00822    0.00599 =
         0.00648   -0.00163    0.00169   -0.00038
C9    1   -0.065099    0.739104    0.346493    11.00000    0.00856    0.00766 =
         0.00881   -0.00007    0.00092   -0.00015
C10   1    0.013255    0.829767    0.383413    11.00000    0.00829    0.00729 =
         0.00826    0.00160    0.00181    0.00023
C11   1    0.049126    0.916287    0.309497    11.00000    0.01151    0.00999 =
         0.01194    0.00182    0.00129   -0.00112
C12   1   -0.163695    0.578878    0.430318    11.00000    0.00838    0.00707 =
         0.01188   -0.00121    0.00075   -0.00008
H1    2    0.028705    0.598868    0.664323    11.00000    0.04198    0.01478 =
         0.02595    0.00131    0.00983    0.00757
H2    2   -0.156816    0.851396    0.673211    11.00000    0.03078    0.02352 =
         0.01994    0.00486    0.00789    0.00809
H3    2   -0.196288    0.932752    0.855899    11.00000    0.03693    0.01912 =
         0.03694   -0.00449    0.01437    0.00810
H4    2   -0.103171    0.846491    1.049525    11.00000    0.03782    0.03199 =
         0.02094   -0.00666    0.01130    0.00427
H5    2    0.032183    0.672692    1.059671    11.00000    0.03303    0.03076 =
         0.01772    0.00655    0.00440    0.00641
H9    2   -0.110050    0.717046    0.254334    11.00000    0.03393    0.02535 =
         0.01300   -0.00217   -0.00006   -0.00431
H111  2   -0.035026    0.979139    0.314167    11.00000    0.05823    0.03677 =
         0.10171    0.03763    0.05199    0.02617
H112  2    0.184899    0.941991    0.337012    11.00000    0.02361    0.05159 =
         0.05669    0.02396    0.00246   -0.01511
H113  2    0.021195    0.895695    0.219446    11.00000    0.13632    0.05101 =
         0.01607    0.00760   -0.00189   -0.04958
hklf 2

REM  ROY-OP orange at 60K SXD 3D prifile fitting integration
REM R1 =  0.0690 for    9984 Fo > 4sig(Fo)  and  0.0690 for all    9984 data
REM    249 parameters refined using      0 restraints

END

WGHT      0.1030     25.1397

REM Highest difference peak  2.230,  deepest hole -2.081,  1-sigma level  0.414
Q1    1   0.0800  0.5790  0.8162  11.00000  0.05    2.23
Q2    1  -0.1935  0.5768  0.4771  11.00000  0.05   -2.08
Q3    1   0.1279  0.5651  0.8386  11.00000  0.05   -2.04
Q4    1  -0.1655  0.8588  0.9150  11.00000  0.05   -2.02
Q5    1   0.0479  0.6795  0.7039  11.00000  0.05   -1.94
Q6    1   0.0801  0.5399  0.8812  11.00000  0.05   -1.92
Q7    1  -0.0445  0.9595  0.2518  11.00000  0.05   -1.91
Q8    1   0.0570  0.5658  0.9425  11.00000  0.05   -1.83
Q9    1   0.0177  0.9032  0.3696  11.00000  0.05   -1.76
Q10   1  -0.2233  0.7095  0.2087  11.00000  0.05   -1.73
;
_shelx_res_checksum              33818

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

data_ROY_OP_60K
_database_code_depnum_ccdc_archive 'CCDC 1878593'
_audit_update_record             
;
2018-11-13 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_LABEL01_ROY_OP_60K          
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_LABEL01_ROY_OP_60K_2        
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_LABEL01_ROY_OP_60K_3        
;
PROBLEM: An _atom_site_label occurs more than once in the atom list. 
RESPONSE: These errors all relate to geometry involving the H atoms on a rotationally-disordered methyl group. The atom labelling of these atoms across different disordered parts appears to give the atoms the same label, leading to these geometric errors. Platon has not interpreted the disorder grouping information given in the CIF by _atom_site_disorder_assembly and _atom_site_disorder_group
;
_vrf_DIFMN02_ROY_OP_60K          
;
PROBLEM: he minimum difference density is < -0.1*zmax*0.75="" _refine_diff_density_min="" given="-1.271" test="" value="-1.200"><a href='javascript:makeHelpWindow("DIFMN_03.html")'>DIFMN03_ALERT_1_C</a> The minimum difference density is < -0.1*zmax*0.75="" the="" relevant="" atom="" site="" should="" be="" identified.=""><a href='javascript:makeHelpWindow("DIFMX_02.html")'>DIFMX02_ALERT_1_C</a> The maximum difference density is > 0.1*ZMAX*0.75
RESPONSE: This alert relates to residual electron density, however our difference maps are calculated from nuclear scattering density. Residual positive and negative densities have approximately the same magnitude. Furthermore, the molecular structure is known and any ambiguities in atomic positioning are going to be most significant around the rotationally disordered methyl group
;
_vrf_DIFMN03_ROY_OP_60K          
;
PROBLEM: he minimum difference density is < -0.1*zmax*0.75="" _refine_diff_density_min="" given="-1.271" test="" value="-1.200"><a href='javascript:makeHelpWindow("DIFMN_03.html")'>DIFMN03_ALERT_1_C</a> The minimum difference density is < -0.1*zmax*0.75="" the="" relevant="" atom="" site="" should="" be="" identified.=""><a href='javascript:makeHelpWindow("DIFMX_02.html")'>DIFMX02_ALERT_1_C</a> The maximum difference density is > 0.1*ZMAX*0.75
RESPONSE: This alert relates to residual electron density, however our difference maps are calculated from nuclear scattering density. Residual positive and negative densities have approximately the same magnitude. Furthermore, the molecular structure is known and any ambiguities in atomic positioning are going to be most significant around the rotationally disordered methyl group
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
_chemical_name_common            ROY-OP
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H9 N3 O2 S'
_chemical_formula_weight         259.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_length_neutron
_atom_type_scat_source
C C 0.0000 0.0000 6.646 'Neutron Data Booklet Table 1.1-8'
H H 0.0000 0.0000 -3.739 'Neutron Data Booklet Table 1.1-8'
N N 0.0000 0.0000 9.360 'Neutron Data Booklet Table 1.1-8'
O O 0.0000 0.0000 5.805 'Neutron Data Booklet Table 1.1-8'
S S 0.0000 0.0000 2.847 'Neutron Data Booklet Table 1.1-8'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   7.670(2)
_cell_length_b                   13.254(3)
_cell_length_c                   11.618(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.066(18)
_cell_angle_gamma                90
_cell_volume                     1145.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    60(2)
_cell_measurement_reflns_used    550
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prismatic
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_F_000             355
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          4
_exptl_crystal_size_mid          3
_exptl_crystal_size_min          2
_exptl_absorpt_coefficient_mu    0.122
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      60(2)

_diffrn_radiation_type           neutron
_diffrn_radiation_details        
;
 white beam
;
_diffrn_source                   'spallation source'
_diffrn_measurement_device_type  'time-of-flight diffractometer'
_diffrn_measurement_method       'time-of-flight profile data'
_diffrn-detector                 'scintillation counters'
_diffrn_detector_area_resol_mean 0.33
_diffrn_detector_details         
;
Array of eleven flat square fiber-optically coupled scintillator PSD 
with 64 x 64 pixels and active area of 192 x 192 mm each
(resolution: 0.33 by 0.33 pixels/mm)
;
_diffrn_reflns_number            8999
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         8.491
_diffrn_reflns_theta_max         88.032
_diffrn_reflns_theta_full        24.835
_diffrn_measured_fraction_theta_max 0.215
_diffrn_measured_fraction_theta_full 0.740
_diffrn_reflns_Laue_measured_fraction_max 0.215
_diffrn_reflns_Laue_measured_fraction_full 0.740
_diffrn_reflns_point_group_measured_fraction_max 0.215
_diffrn_reflns_point_group_measured_fraction_full 0.740
_reflns_number_total             8999
_reflns_number_gt                8999
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       SECI
_computing_cell_refinement       'SXD2001 (Gutmann, 2005)'
_computing_data_reduction        'SXD2001 (Gutmann, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury 3.6, (CCDC 2015)'
_computing_publication_material  'Mercury 3.6, (CCDC 2015)'

_refine_special_details          
;
 Refinement of F² against ALL unmerged Laue reflections.
 R1=0.0660 for 3674 unique reflections after merging for Fourier.
 
 CheckCIF alerts
 
PROBLEM: An _atom_site_label occurs more than once in the atom list.
PROBLEM: Duplicate Atomic Label on INPUT ................       H111 Note  
PROBLEM: Angle   Calc    109.5(6), Rep    112.4(6), Dev..       4.83 Sigma 
PROBLEM: H...A   Calc   2.675(12), Rep    2.306(9), Dev..      30.75 Sigma 
PROBLEM: D-H..A  Calc    111.4(7), Rep    141.5(8), Dev..      43.00 Sigma 
PROBLEM: Bond    Calc    1.076(7), Rep    1.086(5), Dev..       1.43 Sigma 
PROBLEM: D-H     Calc    1.076(7), Rep    1.086(5), Dev..       1.43 Sigma 

RESPONSE: These alerts relate to residual electron density, however
our difference maps are calculated from nuclear scattering density. Residual
positive and negative densities have approximately the same magnitude.
Furthermore, the molecular structure is known and any ambiguities in atomic
positioning are going to be most significant around the rotationally 
disordered methyl group.


PROBLEM: The minimum difference density is < -0.1*ZMAX*0.75
PROBLEM: The maximum difference density is > 0.1*ZMAX*0.75

RESPONSE: These alerts relate to residual electron density, however
our difference maps are calculated from nuclear scattering density. Residual
positive and negative densities have approximately the same magnitude.
Furthermore, the molecular structure is known and any ambiguities in atomic
positioning are going to be most significant around the rotationally 
disordered methyl group.


PROBLEM: Missing _cell_measurement_theta_min Value ......     Please Do ! 
PROBLEM: Missing _cell_measurement_theta_max Value ......     Please Do ! 

RESPONSE: Not applicable - data were measured by the time-of-flight method
using a white beam.


PROBLEM: No Datum for _diffrn_reflns_av_R_equivalents ...     Please Do ! 

RESPONSE: Not applicable - statistics on equivalent reflections are not available
as they are measured at different wavelengths. A statement regarding Rmerging 
statistics is given at the start of this section.


PROBLEM: No (Interpretable) Reflections Found in FCF ....     Please Check

RESPONSE: No action taken. The hkl reflection list is provided at the end of this CIF.


PROBLEM: Short Inter XH3 .. XHn     H113     ..H4       .       2.04 Ang.  

RESPONSE: No action taken. This is short, but not impossibly so - it lies toward
the lower end of a histogram of H...H contact distances in the CSD. This error
relates to a disordered hydrogen atom on the methyl group.
;


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0073(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8999
_refine_ls_number_parameters     243
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0718
_refine_ls_wR_factor_ref         0.1909
_refine_ls_wR_factor_gt          0.1909
_refine_ls_goodness_of_fit_ref   1.551
_refine_ls_restrained_S_all      1.559
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S 0.0680(5) 0.8380(3) 0.5353(5) 0.0101(9) Uani 1 1 d . . . . .
O1 O 0.1721(3) 0.53885(19) 0.9859(3) 0.0183(6) Uani 1 1 d . . . . .
O2 O 0.0660(4) 0.51126(19) 0.7991(3) 0.0216(6) Uani 1 1 d . . . . .
N1 N -0.00851(15) 0.67213(10) 0.65965(17) 0.0122(3) Uani 1 1 d . . . . .
N2 N -0.22506(15) 0.49859(10) 0.42336(18) 0.0155(4) Uani 1 1 d . . . . .
N3 N 0.09015(14) 0.56697(10) 0.88729(17) 0.0128(3) Uani 1 1 d . . . . .
C1 C -0.03379(18) 0.71593(13) 0.7618(2) 0.0098(4) Uani 1 1 d . . . . .
C2 C -0.1108(2) 0.81290(13) 0.7597(2) 0.0110(4) Uani 1 1 d . . . . .
C3 C -0.1327(2) 0.85829(14) 0.8621(2) 0.0136(5) Uani 1 1 d . . . . .
C4 C -0.0797(2) 0.80986(16) 0.9717(3) 0.0156(5) Uani 1 1 d . . . . .
C5 C -0.0055(2) 0.71469(15) 0.9769(2) 0.0133(5) Uani 1 1 d . . . . .
C6 C 0.01593(19) 0.66792(13) 0.8738(2) 0.0099(4) Uani 1 1 d . . . . .
C7 C -0.02067(18) 0.72038(13) 0.5523(2) 0.0097(4) Uani 1 1 d . . . . .
C8 C -0.08542(18) 0.67642(12) 0.4422(2) 0.0099(4) Uani 1 1 d . . . . .
C9 C -0.06523(19) 0.73898(13) 0.3468(2) 0.0102(4) Uani 1 1 d . . . . .
C10 C 0.01324(19) 0.82958(13) 0.3834(2) 0.0100(4) Uani 1 1 d . . . . .
C11 C 0.0490(2) 0.91575(14) 0.3095(2) 0.0145(5) Uani 1 1 d D . . . .
C12 C -0.16398(19) 0.57887(13) 0.4308(2) 0.0114(4) Uani 1 1 d . . . . .
H1 H 0.0295(7) 0.5987(3) 0.6652(6) 0.0288(12) Uani 1 1 d . . . . .
H2 H -0.1560(6) 0.8511(4) 0.6746(6) 0.0268(11) Uani 1 1 d . . . . .
H3 H -0.1951(6) 0.9322(4) 0.8573(7) 0.0333(14) Uani 1 1 d . . . . .
H4 H -0.1024(7) 0.8462(4) 1.0503(7) 0.0337(13) Uani 1 1 d . . . . .
H5 H 0.0326(6) 0.6727(4) 1.0602(6) 0.0297(12) Uani 1 1 d . . . . .
H9 H -0.1096(6) 0.7167(4) 0.2536(6) 0.0300(13) Uani 1 1 d . . . . .
H111 H -0.0550(10) 0.9722(6) 0.2962(11) 0.0308(19) Uiso 0.49(2) 1 d D U P A 1
H112 H 0.1772(9) 0.9516(8) 0.3479(10) 0.0308(19) Uiso 0.49(2) 1 d D U P A 1
H113 H 0.0542(13) 0.8865(7) 0.2228(7) 0.0308(19) Uiso 0.49(2) 1 d D U P A 1
H111 H -0.0086(13) 0.9852(6) 0.3364(11) 0.036(2) Uiso 0.51(2) 1 d D U P A 2
H112 H 0.1907(7) 0.9285(8) 0.3205(11) 0.036(2) Uiso 0.51(2) 1 d D U P A 2
H113 H -0.0146(14) 0.9043(8) 0.2168(6) 0.036(2) Uiso 0.51(2) 1 d D U P A 2

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
S 0.0131(12) 0.0082(14) 0.009(3) -0.0005(17) 0.0027(14) 0.0002(10)
O1 0.0158(7) 0.0226(11) 0.0154(17) 0.0065(12) 0.0018(8) 0.0049(7)
O2 0.0369(11) 0.0120(10) 0.017(2) 0.0019(11) 0.0079(11) 0.0072(8)
N1 0.0183(4) 0.0078(5) 0.0112(9) 0.0005(6) 0.0048(5) 0.0022(3)
N2 0.0142(4) 0.0099(5) 0.0205(11) -0.0006(6) 0.0006(5) -0.0024(3)
N3 0.0126(4) 0.0138(5) 0.0130(10) 0.0042(6) 0.0050(5) 0.0024(3)
C1 0.0092(5) 0.0082(6) 0.0122(13) -0.0003(7) 0.0031(6) -0.0013(4)
C2 0.0129(5) 0.0091(7) 0.0121(13) -0.0012(8) 0.0053(6) 0.0005(4)
C3 0.0151(6) 0.0123(7) 0.0153(14) -0.0032(9) 0.0073(7) -0.0002(5)
C4 0.0164(6) 0.0171(8) 0.0148(15) -0.0041(9) 0.0066(7) -0.0012(5)
C5 0.0125(5) 0.0175(8) 0.0101(14) -0.0016(9) 0.0032(6) -0.0003(5)
C6 0.0099(5) 0.0112(7) 0.0092(12) -0.0008(7) 0.0034(6) -0.0011(4)
C7 0.0107(5) 0.0075(6) 0.0106(12) -0.0017(7) 0.0020(5) -0.0001(4)
C8 0.0093(4) 0.0078(6) 0.0123(12) -0.0003(8) 0.0020(5) 0.0003(4)
C9 0.0105(5) 0.0099(7) 0.0095(13) 0.0001(8) 0.0008(6) 0.0005(4)
C10 0.0097(5) 0.0092(6) 0.0110(12) 0.0020(7) 0.0021(6) 0.0005(4)
C11 0.0151(6) 0.0126(7) 0.0145(14) 0.0032(9) 0.0009(7) -0.0020(5)
C12 0.0103(5) 0.0083(6) 0.0147(13) -0.0006(8) 0.0013(6) -0.0001(4)
H1 0.054(2) 0.0131(16) 0.022(4) 0.003(2) 0.013(2) 0.0087(15)
H2 0.0368(19) 0.0237(19) 0.021(4) 0.004(2) 0.0085(19) 0.0100(14)
H3 0.044(2) 0.022(2) 0.038(4) -0.004(2) 0.018(2) 0.0100(15)
H4 0.046(2) 0.037(3) 0.021(4) -0.008(3) 0.012(2) 0.0041(19)
H5 0.0352(18) 0.034(2) 0.019(3) 0.005(3) 0.0043(18) 0.0054(16)
H9 0.0344(18) 0.031(2) 0.021(4) -0.004(2) -0.0008(19) -0.0046(15)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S C10 1.715(7) . ?
S C7 1.731(4) . ?
O1 N3 1.223(3) . ?
O2 N3 1.239(4) . ?
N1 C1 1.377(3) . ?
N1 C7 1.384(3) . ?
N1 H1 1.014(4) . ?
N2 C12 1.157(2) . ?
N3 C6 1.448(2) . ?
C1 C2 1.412(2) . ?
C1 C6 1.414(3) . ?
C2 C3 1.379(3) . ?
C2 H2 1.090(7) . ?
C3 C4 1.396(4) . ?
C3 H3 1.086(5) . ?
C4 C5 1.379(3) . ?
C4 H4 1.082(8) . ?
C5 C6 1.394(3) . ?
C5 H5 1.093(7) . ?
C7 C8 1.384(3) . ?
C8 C12 1.419(2) . ?
C8 C9 1.422(3) . ?
C9 C10 1.364(2) . ?
C9 H9 1.093(7) . ?
C10 C11 1.494(3) . ?
C11 H111 1.078(6) . ?
C11 H112 1.086(5) . ?
C11 H113 1.089(6) . ?
C11 H111 1.099(6) . ?
C11 H112 1.076(6) . ?
C11 H113 1.080(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 S C7 93.1(2) . . ?
C1 N1 C7 126.08(14) . . ?
C1 N1 H1 116.7(4) . . ?
C7 N1 H1 117.1(4) . . ?
O1 N3 O2 122.1(2) . . ?
O1 N3 C6 118.8(2) . . ?
O2 N3 C6 119.0(2) . . ?
N1 C1 C2 121.0(2) . . ?
N1 C1 C6 122.68(15) . . ?
C2 C1 C6 116.3(2) . . ?
C3 C2 C1 121.3(2) . . ?
C3 C2 H2 120.1(3) . . ?
C1 C2 H2 118.6(3) . . ?
C2 C3 C4 121.13(18) . . ?
C2 C3 H3 119.6(5) . . ?
C4 C3 H3 119.3(4) . . ?
C5 C4 C3 119.1(2) . . ?
C5 C4 H4 121.3(4) . . ?
C3 C4 H4 119.6(4) . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 121.5(4) . . ?
C6 C5 H5 118.2(4) . . ?
C5 C6 C1 121.90(17) . . ?
C5 C6 N3 116.31(19) . . ?
C1 C6 N3 121.79(19) . . ?
N1 C7 C8 124.68(15) . . ?
N1 C7 S 125.2(2) . . ?
C8 C7 S 109.6(3) . . ?
C7 C8 C12 121.2(2) . . ?
C7 C8 C9 113.11(16) . . ?
C12 C8 C9 125.6(2) . . ?
C10 C9 C8 113.2(2) . . ?
C10 C9 H9 123.7(3) . . ?
C8 C9 H9 123.2(3) . . ?
C9 C10 C11 128.5(2) . . ?
C9 C10 S 110.9(2) . . ?
C11 C10 S 120.6(2) . . ?
C10 C11 H111 112.4(6) . . ?
C10 C11 H112 111.9(7) . . ?
H111 C11 H112 108.6(5) . . ?
C10 C11 H113 108.2(6) . . ?
H111 C11 H113 107.9(6) . . ?
H112 C11 H113 107.6(6) . . ?
C10 C11 H111 109.5(7) . . ?
C10 C11 H112 111.9(7) . . ?
H111 C11 H112 107.4(5) . . ?
C10 C11 H113 111.4(6) . . ?
H111 C11 H113 106.6(6) . . ?
H112 C11 H113 109.9(6) . . ?
N2 C12 C8 178.6(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C7 S 43.4(2) . . . . ?
C2 C1 N1 C7 12.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 1.014(4) 1.906(7) 2.655(3) 128.2(5) .
N1 H1 N2 1.014(4) 2.391(5) 3.178(2) 133.7(5) 3_566
C2 H2 S 1.090(7) 2.636(8) 3.244(6) 114.5(3) .
C11 H112 O1 1.086(5) 2.306(9) 3.228(3) 141.5(8) 2_556
C11 H111 S 1.099(6) 2.872(8) 3.936(5) 163.0(9) 3_576
C11 H113 N2 1.080(6) 2.573(10) 3.381(3) 131.0(8) 2_455

_refine_diff_density_max         2.400
_refine_diff_density_min         -2.685
_refine_diff_density_rms         0.388

_shelx_res_file                  
;

    roy60_3d.res created by SHELXL-2014/7


TITL ROY-OP orange at 60K SXD 3D profile fitting integration
CELL 0.7 7.6700   13.2536   11.6179   90.0000  104.066   90.0000
ZERR  4.0   0.0024    0.0034    0.0037    0.000     0.018   0.000
LATT  1
SYMM 1/2-x,1/2+y,1/2-z
SFAC  C   0 0 0 0 0 0 0 0  6.64800   0.000   0.000     0.035   0.76   12.010
SFAC  H   0 0 0 0 0 0 0 0 -3.74100   0.000   0.000     38.00   0.31    1.008
SFAC  N   0 0 0 0 0 0 0 0  9.36000   0.000   0.000     1.90    0.70   14.007
SFAC  O   0 0 0 0 0 0 0 0  5.80500   0.000   0.000     0.0019  0.66   15.999
SFAC  S   0 0 0 0 0 0 0 0  2.84700   0.000   0.000     0.52    1.02   32.065
UNIT 48 36 12 8 4

L.S. 5
BOND $H
REM Hydrogen bonds with esds
HTAB N1 O2
EQIV $1 -x, -y+1, -z+1
HTAB N1 N2_$1
HTAB C2 S
EQIV $2 -x+1/2, y+1/2, -z+3/2
HTAB C11 O1_$2
EQIV $3 -x, -y+2, -z+1
HTAB C11 S_$3
EQIV $4 -x-1/2, y+1/2, -z+1/2
HTAB C11 N2_$4
CONF C1 N1 C7 S
CONF C2 C1 N1 C7
MPLA C1 C2 C3 C4 C5 C6
MPLA S C7 C8 C9 C10
ACTA
MERG 0
FMAP -2
PLAN 10
temp  -213

omit     0  -2  -4
omit    -6  -1   1
omit     3   3   0
omit    -1  -2   0
omit    -5  -9  -4
omit     5   2  -4
omit     2   2   2
omit    -2  -6  -1
omit    -2   7  -2
omit     8   1  -1
omit    -1 -19   4

sadi 0.005 c11 h111 c11 h112 c11 h113
sadi 0.005 h111 h112 h111 h113 h112 h113

WGHT    0.100000
EXTI    0.007309
BASF   0.94830   0.76458   0.77391   0.81074
FVAR       0.34925   0.49205   0.03078   0.03583
S     5    0.067952    0.837992    0.535347    11.00000    0.01314    0.00819 =
         0.00908   -0.00045    0.00267    0.00022
O1    4    0.172085    0.538852    0.985893    11.00000    0.01576    0.02264 =
         0.01539    0.00649    0.00182    0.00486
O2    4    0.065966    0.511265    0.799139    11.00000    0.03688    0.01199 =
         0.01653    0.00189    0.00788    0.00724
N1    3   -0.008510    0.672128    0.659651    11.00000    0.01826    0.00779 =
         0.01118    0.00055    0.00484    0.00222
N2    3   -0.225064    0.498595    0.423364    11.00000    0.01421    0.00987 =
         0.02051   -0.00055    0.00058   -0.00244
N3    3    0.090149    0.566966    0.887287    11.00000    0.01256    0.01378 =
         0.01303    0.00425    0.00503    0.00242
C1    1   -0.033793    0.715934    0.761807    11.00000    0.00920    0.00817 =
         0.01221   -0.00034    0.00308   -0.00132
C2    1   -0.110801    0.812901    0.759686    11.00000    0.01289    0.00907 =
         0.01209   -0.00123    0.00534    0.00050
C3    1   -0.132721    0.858286    0.862085    11.00000    0.01507    0.01231 =
         0.01534   -0.00321    0.00734   -0.00022
C4    1   -0.079680    0.809857    0.971729    11.00000    0.01642    0.01707 =
         0.01483   -0.00413    0.00662   -0.00116
C5    1   -0.005539    0.714687    0.976879    11.00000    0.01254    0.01749 =
         0.01011   -0.00161    0.00320   -0.00028
C6    1    0.015929    0.667918    0.873750    11.00000    0.00994    0.01124 =
         0.00921   -0.00079    0.00340   -0.00109
C7    1   -0.020674    0.720383    0.552348    11.00000    0.01066    0.00747 =
         0.01061   -0.00169    0.00204   -0.00010
C8    1   -0.085421    0.676416    0.442156    11.00000    0.00929    0.00778 =
         0.01230   -0.00026    0.00200    0.00028
C9    1   -0.065231    0.738977    0.346801    11.00000    0.01046    0.00993 =
         0.00950    0.00011    0.00079    0.00048
C10   1    0.013239    0.829580    0.383449    11.00000    0.00969    0.00922 =
         0.01097    0.00202    0.00207    0.00049
C11   1    0.049044    0.915750    0.309484    11.00000    0.01510    0.01259 =
         0.01454    0.00323    0.00093   -0.00205
C12   1   -0.163981    0.578875    0.430765    11.00000    0.01027    0.00833 =
         0.01472   -0.00063    0.00130   -0.00009
H1    2    0.029545    0.598663    0.665156    11.00000    0.05367    0.01307 =
         0.02172    0.00329    0.01321    0.00870
H2    2   -0.155984    0.851085    0.674584    11.00000    0.03678    0.02366 =
         0.02083    0.00423    0.00847    0.00999
H3    2   -0.195122    0.932218    0.857301    11.00000    0.04428    0.02162 =
         0.03822   -0.00381    0.01793    0.00996
H4    2   -0.102371    0.846151    1.050251    11.00000    0.04611    0.03655 =
         0.02058   -0.00775    0.01203    0.00410
H5    2    0.032560    0.672682    1.060241    11.00000    0.03518    0.03405 =
         0.01879    0.00488    0.00428    0.00536
H9    2   -0.109614    0.716719    0.253644    11.00000    0.03444    0.03070 =
         0.02098   -0.00361   -0.00077   -0.00463
rem
rem rotationally disordered methyl group
part 1
H111  2   -0.054993    0.972246    0.296175    21.00000   31.00000
H112  2    0.177226    0.951635    0.347854    21.00000   31.00000
H113  2    0.054231    0.886480    0.222755    21.00000   31.00000
part 2
H111  2   -0.008570    0.985208    0.336400   -21.00000   41.00000
H112  2    0.190653    0.928517    0.320503   -21.00000   41.00000
H113  2   -0.014633    0.904308    0.216768   -21.00000   41.00000
part 0

hklf 2

REM  ROY-OP orange at 60K SXD 3D profile fitting integration
REM R1 =  0.0718 for    8999 Fo > 4sig(Fo)  and  0.0718 for all    8999 data
REM    243 parameters refined using     30 restraints

END

WGHT      0.1031     25.4897

REM Highest difference peak  2.400,  deepest hole -2.685,  1-sigma level  0.388
Q1    1  -0.0167  0.9604  0.3217  11.00000  0.05    2.40
Q2    1  -0.0623  0.9470  0.2527  11.00000  0.05   -2.23
Q3    1   0.1552  0.9230  0.3658  11.00000  0.05    2.09
Q4    1   0.1283  0.5696  0.8468  11.00000  0.05   -1.88
Q5    1   0.1168  0.8786  0.2344  11.00000  0.05   -1.88
Q6    1  -0.1939  0.5712  0.4730  11.00000  0.05   -1.86
Q7    1  -0.0424  0.6710  0.6978  11.00000  0.05   -1.79
Q8    1   0.0656  0.9881  0.3648  11.00000  0.05   -1.79
Q9    1   0.2123  0.9388  0.2939  11.00000  0.05    1.76
Q10   1  -0.2230  0.6588  0.5341  11.00000  0.05   -1.69
;
_shelx_res_checksum              6213
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
