One-step facile transformation from rofecoxib to reversible mechanofluorochromic materials with dual-state emission
Chen, Zhong; Wang, Zexin; Liu, Wei; Wei, Yongbo; Ye, Yuqiu; Ke, Yanbing; Wu, Tong; Chen, Nannan; Zhou, Jingming; Zhang, Xiaopo; Tan, Yingfeng; Jiang, Hong; Zhai, Xin; Xie, Lijun; New Journal of Chemistry 47 (2023) 12839–12849; doi:10.1039/D3NJ02402D

data_7062576
_publ_section_title
;
 One-step facile transformation from rofecoxib to reversible
 mechanofluorochromic materials with dual-state emission
;
_journal_issue                   27
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12839
_journal_page_last               12849
_journal_paper_doi               10.1039/D3NJ02402D
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C29 H26 N O6 S, 0.55(C2 N)'
_chemical_formula_sum            'C30.1 H26 N1.55 O6 S'
_chemical_formula_weight         537.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-10-10
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-10-25 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.023(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.5736(14)
_cell_length_b                   13.0560(9)
_cell_length_c                   24.5284(18)
_cell_measurement_reflns_used    3698
_cell_measurement_temperature    301.2(3)
_cell_measurement_theta_max      29.5150
_cell_measurement_theta_min      2.0320
_cell_volume                     5483.1(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      301.2(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     -6.00  57.00   0.50   10.00    --    0.09  44.00 168.00  126
  2  \w    -68.00  12.00   0.50   10.00    --    0.09 -44.00  17.00  160
  3  \w      5.00  30.00   0.50   10.00    --    0.09 -99.00   0.00   50
  4  \w    -18.00  34.00   0.50   10.00    --    0.09 -99.00 -60.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0154012000
_diffrn_orient_matrix_UB_12      -0.0018379000
_diffrn_orient_matrix_UB_13      0.0293189000
_diffrn_orient_matrix_UB_21      -0.0316782000
_diffrn_orient_matrix_UB_22      0.0300759000
_diffrn_orient_matrix_UB_23      0.0043817000
_diffrn_orient_matrix_UB_31      -0.0217563000
_diffrn_orient_matrix_UB_32      -0.0452047000
_diffrn_orient_matrix_UB_33      0.0016811000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0730
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            17466
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.029
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82565
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear greenish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       block
_exptl_crystal_F_000             2252
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         4714
_refine_ls_number_restraints     104
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1143
_refine_ls_R_factor_gt           0.0700
_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/[\s^2^(Fo^2^)+(0.0798P)^2^+7.7217P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1636
_refine_ls_wR_factor_ref         0.1919
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2928
_reflns_number_total             4714
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj02402d2.cif
_cod_data_source_block           n2_rt_auto
_cod_original_formula_sum        'C30.10 H26 N1.55 O6 S'
_cod_database_code               7062576
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.953
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-C3
 1.14 with sigma of 0.02
 C3-C4
 1.456 with sigma of 0.01
 C3-N2
 1.137 with sigma of 0.01
 C4-N2
 2.593 with sigma of 0.02
 N2-C4
 2.59 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
N2 \\sim C3 \\sim C4: within 2A with sigma of 0.04 and sigma for terminal atoms
of 0.08 within 2A
Uanis(S01) \\sim Ueq, Uanis(O008) \\sim Ueq, Uanis(C00Z) \\sim Ueq, Uanis(O004)
\\sim Ueq, Uanis(C00G) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C011) \\sim Ueq, Uanis(C00T) \\sim Ueq, Uanis(C010) \\sim Ueq,
Uanis(C00Y) \\sim Ueq, Uanis(O003) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 N2, C3, C4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(N2)=Sof(C3)=Sof(C4)=1-FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00U(H00U), C00V(H00V),
 C00W(H00W), C00X(H00X)
6.b Idealised Me refined as rotating group:
 C00Y(H00A,H00B,H00C), C00Z(H00D,H00E,H00F), C010(H01A,H01B,H01C), C011(H01D,
 H01E,H01F)
;
_shelx_res_checksum              62589
_shelx_hkl_checksum              34269
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.303
_oxdiff_exptl_absorpt_empirical_full_min 0.785