Reversible piezochromism in a molecular wine-rack
Elena L. Harty; Alex R. Ha; Mark R. Warren; Amber L. Thompson; David R. Allan; Andrew L. Goodwin; Nicholas P. Funnell; Chem.Commun. 51 (2015) 10608–; doi:10.1039/C5cc02916C

data_7117346
_publ_section_title
;
 Reversible piezochromism in a molecular wine-rack
;
_journal_name_full               Chem.Commun.
_journal_page_first              10608
_journal_paper_doi               10.1039/C5cc02916C
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration .
_chemical_compound_source        'TCI Chemicals'
_chemical_formula_moiety         'C12 H9 N3 O2 S1'
_chemical_formula_sum            'C12 H9 N3 O2 S'
_chemical_formula_weight         259.29
_chemical_name_common            ROY
_chemical_name_systematic
5-methyl-2-((2-nitrophenyl)amino)-3-thiophenecarbonitrile
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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     direct
_audit_creation_date             14-12-16
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2015-04-07 deposited with the CCDC.
2015-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.78(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5322(17)
_cell_length_b                   16.412(3)
_cell_length_c                   8.4958(17)
_cell_measurement_reflns_used    2475
_cell_measurement_temperature    293
_cell_measurement_theta_max      28
_cell_measurement_theta_min      4
_cell_volume                     1189.1(4)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'User-defined model'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.845
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.023
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5816
_diffrn_reflns_theta_full        25.203
_diffrn_reflns_theta_max         29.650
_diffrn_reflns_theta_min         3.333
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.106
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9671
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2825
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.0002834
_refine_ls_shift/su_mean         0.0000297
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.66P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1076
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1074
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              10
_reflns_limit_l_min              0
_reflns_number_gt                2174
_reflns_number_total             2826
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.15
_oxford_diffrn_Wilson_scale      5.89
_oxford_refine_ls_r_factor_ref   0.0587
_oxford_refine_ls_scale          0.4431(8)
_oxford_reflns_number_all        2826
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_oxford_structure_analysis_title 'ROY Y-form, ambient pressure'
_cod_data_source_file            c5cc02916c3.cif
_cod_data_source_block           ROY_Y_ambient
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_original_formula_sum        'C12 H9 N3 O2 S1'
_cod_database_code               7117346
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  18,X'S) H   ( 183,X'S) H   ( 182,X'S) H   ( 181,X'S) 
RIDE N   (   6,X'S) H   (  61,X'S) 
END    

block
CONT H(   31 ,X,Y,Z,U[ISO])
CONT H(   81 ,X,Y,Z,U[ISO])
CONT H(   91 ,X,Y,Z,U[ISO])
CONT H(  101 ,X,Y,Z,U[ISO])
CONT H(  111 ,X,Y,Z,U[ISO])
CONT H(  183 ,X,Y,Z,U[ISO])
CONT H(  182 ,X,Y,Z,U[ISO])
CONT H(  181 ,X,Y,Z,U[ISO])
CONT H(   61 ,X,Y,Z,U[ISO])
END
;
_iucr_refine_instruction_details_restraints
;
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 3) to H(31) 
REST 0.047, 0.002 = H(31,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(31) TO C ( 3) TO C(2) 
CONT H(31) TO C ( 3) TO C(4) 
PLANAR C ( 3) C(2) C(4) H(31) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 8) to H(81) 
REST 0.058, 0.002 = H(81,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(81) TO C ( 8) TO C(7) 
CONT H(81) TO C ( 8) TO C(9) 
PLANAR C ( 8) C(7) C(9) H(81) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 9) to H(91) 
REST 0.074, 0.002 = H(91,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(91) TO C ( 9) TO C(8) 
CONT H(91) TO C ( 9) TO C(10) 
PLANAR C ( 9) C(8) C(10) H(91) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 10) to H(101) 
REST 0.080, 0.002 = H(101,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(101) TO C ( 10) TO C(9) 
CONT H(101) TO C ( 10) TO C(11) 
PLANAR C ( 10) C(9) C(11) H(101) 
REM            1 H on sp 2
DIST 0.93, 0.02 = 
CONT C ( 11) to H(111) 
REST 0.068, 0.002 = H(111,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(111) TO C ( 11) TO C(10) 
CONT H(111) TO C ( 11) TO C(12) 
PLANAR C ( 11) C(10) C(12) H(111) 
REM            3 H on sp 3
DIST 0.96, 0.02 = 
CONT C ( 18) to H(183) 
CONT C ( 18) to H(182) 
CONT C ( 18) to H(181) 
REST 0.080, 0.002 = H(183,U[ISO]) 
REST 0.080, 0.002 = H(182,U[ISO]) 
REST 0.080, 0.002 = H(181,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(2) to C ( 18) to H(183) 
CONT C(2) to C ( 18) to H(182) 
CONT C(2) to C ( 18) to H(181) 
ANGLE 0.0, 2.0 = mean H(183) to C ( 18) to H(182) 
CONT H(183) to C ( 18) to H(181) 
CONT H(182) to C ( 18) to H(181) 
REM            H1-N-R2
DIST 0.86, 0.02 = 
CONT N ( 6) to H(61) 
REST 0.046, 0.002 = H(61,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(61) TO N ( 6) TO C(5) 
CONT H(61) TO N ( 6) TO C(7) 
PLANAR 0.010000  C(5) C(7) N(6) H(61) 
END
;