#------------------------------------------------------------------------------
#$Date: 2024-11-15 21:31:15 +0200 (Fri, 15 Nov 2024) $
#$Revision: 295944 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/20/7232047.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7232047
loop_
_publ_author_name
'Funnell, Nicholas P.'
'Bull, Craig L.'
'Ridley, Christopher J.'
'Capelli, Silvia'
_publ_section_title
;
 Structural behaviour of OP-ROY at extreme conditions
;
_journal_issue                   30
_journal_name_full               CrystEngComm
_journal_page_first              4473
_journal_paper_doi               10.1039/C8CE01946K
_journal_volume                  21
_journal_year                    2019
_chemical_formula_sum            'C12 H9 N3 O2 S'
_chemical_formula_weight         259.28
_chemical_name_common            ROY-OP
_chemical_name_systematic
5-methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-11-13 deposited with the CCDC.
2018-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.118(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.651(2)
_cell_length_b                   13.243(3)
_cell_length_c                   11.624(4)
_cell_measurement_reflns_used    550
_cell_measurement_temperature    40(2)
_cell_volume                     1142.2(6)
_computing_cell_refinement       'SXD2001 (Gutmann, 2005)'
_computing_data_collection       SECI
_computing_data_reduction        'SXD2001 (Gutmann, 2017)'
_computing_molecular_graphics    'Mercury 3.6, (CCDC 2015)'
_computing_publication_material  'Mercury 3.6, (CCDC 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      166(13)
_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_measured_fraction_theta_full 0.740
_diffrn_measured_fraction_theta_max 0.153
_diffrn_measurement_device_type  'time-of-flight diffractometer'
_diffrn_measurement_method       'time-of-flight profile data'
_diffrn_radiation_probe          neutron
_diffrn_radiation_type           'white beam'
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_Laue_measured_fraction_full 0.740
_diffrn_reflns_Laue_measured_fraction_max 0.153
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9984
_diffrn_reflns_point_group_measured_fraction_full 0.740
_diffrn_reflns_point_group_measured_fraction_max 0.153
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         86.766
_diffrn_reflns_theta_min         8.284
_diffrn_source                   'spallation source'
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             355
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetone'
_exptl_crystal_size_max          4
_exptl_crystal_size_mid          3
_exptl_crystal_size_min          2
_refine_diff_density_max         2.230
_refine_diff_density_min         -2.081
_refine_diff_density_rms         0.414
_refine_ls_extinction_coef       0.0080(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.448
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         9984
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.448
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0690
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1795
_refine_ls_wR_factor_ref         0.1795
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9984
_reflns_number_total             9984
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce01946k2.cif
_cod_data_source_block           ROY_OP_40K
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_ambient_temperature' value '40 - 293' was changed to
'166(13)' - the average value was taken and precision was estimated.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7232030--7232048.cif.
;
_cod_database_code               7232047
_shelx_shelxl_version_number     2014/7
_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'
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
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_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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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_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
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
C1 N1 C7 S 43.2(2)
C2 C1 N1 C7 12.80(18)
loop_
_cod_changelog_entry_id
_cod_changelog_entry_author
_cod_changelog_entry_date
_cod_changelog_entry_text
1 'Vaitkus, Antanas' 2024-11-15T21:30:00+02:00
;
 Renamed data items '_diffrn-detector', '_diffrn_radiation_type' and
 '_diffrn_radiation_details' to '_diffrn_detector', '_diffrn_radiation_probe'
 and '_diffrn_radiation_type' respectively.
;
