D-A-D Structured Bis-acylhydrazone Exhibiting Aggregation-Induced Emission, Mechanochromic Luminescence, and Al(III) Detection.
Santhiya, Kuppusamy; Sen, Shovan K.; Natarajan, Ramalingam; Shankar, Ramasamy; Murugesapandian, Balasubramanian; The Journal of organic chemistry 83 (2018) 10770–10775; doi:10.1021/acs.joc.8b01377

data_4035629
_publ_section_title
;
 D-A-D Structured Bis-acylhydrazone Exhibiting Aggregation-Induced
 Emission, Mechanochromic Luminescence, and Al(III) Detection.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10770
_journal_page_last               10775
_journal_paper_doi               10.1021/acs.joc.8b01377
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C29 H35 N7 O4, H2 O'
_chemical_formula_sum            'C29 H37 N7 O5'
_chemical_formula_weight         563.65
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-12-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.161(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8583(5)
_cell_length_b                   10.4135(5)
_cell_length_c                   27.9889(15)
_cell_measurement_reflns_used    4995
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.01
_cell_measurement_theta_min      2.86
_cell_volume                     2850.9(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            18932
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.431
_diffrn_reflns_theta_min         2.857
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0939 before and 0.0513 after correction. The Ratio of minimum to maximum transmission is 0.9316. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2900
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0687
_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^)+(0.0800P)^2^+4.1483P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1813
_refine_ls_wR_factor_ref         0.2057
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1918
_reflns_number_total             2900
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01377_si_002.cif
_cod_data_source_block           rn_ss7a200717_0m_a
_cod_database_code               4035629
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.978
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O3-H3A = O3-H3B
 0.85 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C14 \\sim C12: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
C15 \\sim C13: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
4. Others
 Fixed Sof: O3(0.5) H3A(0.5) H3B(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2A), C2(H2B), C3(H3), C5(H5), C7(H7), C8(H8), C10(H10)
5.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
5.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              64941
_shelx_hkl_checksum              21913
_olex2_submission_special_instructions 'No special instructions were received'