Solution and Solid-State Emission Toggling of a Photochromic Hydrazone.
Shao, Baihao; Baroncini, Massimo; Qian, Hai; Bussotti, Laura; Di Donato, Mariangela; Credi, Alberto; Aprahamian, Ivan; Journal of the American Chemical Society 140 (2018) 12323–12327; doi:10.1021/jacs.8b07108

data_4132882
_publ_section_title
;
 Solution and Solid-State Emission Toggling of a Photochromic Hydrazone.
;
_journal_issue                   39
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12323
_journal_page_last               12327
_journal_paper_doi               10.1021/jacs.8b07108
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C18 H21 N3 O2'
_chemical_formula_sum            'C18 H21 N3 O2'
_chemical_formula_weight         311.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2017-01-19
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_cell_angle_alpha                102.122(3)
_cell_angle_beta                 92.757(3)
_cell_angle_gamma                90.570(3)
_cell_formula_units_Z            2
_cell_length_a                   4.9956(2)
_cell_length_b                   9.5201(4)
_cell_length_c                   17.7596(7)
_cell_measurement_reflns_used    1415
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      70.05
_cell_measurement_theta_min      2.55
_cell_volume                     824.66(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w and \f'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0822
_diffrn_reflns_av_unetI/netI     0.0773
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9656
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.291
_diffrn_reflns_theta_min         2.548
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0689 before and 0.0530 after correction. The Ratio of minimum to maximum transmission is 0.8838. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_description       needle
_exptl_crystal_F_000             332
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.263
_exptl_crystal_size_mid          0.027
_exptl_crystal_size_min          0.023
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3011
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0585
_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^)+(0.0695P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1527
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1690
_reflns_number_total             3011
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b07108_si_002.cif
_cod_data_source_block           ia117c
_cod_database_code               4132882
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.844
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: C4(0.5) H4(0.5) C4B(0.5) H4B(0.5) C5(0.5) H5(0.5) C5B(0.5)
 H5B(0.5) C7(0.5) H7(0.5) C7B(0.5) H7B(0.5) C8(0.5) H8(0.5) C8B(0.5) H8B(0.5)
 C9(0.5) H9A(0.5) H9B(0.5) H9C(0.5) C9B(0.5) H9BA(0.5) H9BB(0.5) H9BC(0.5)
 C10(0.5) H10A(0.5) H10B(0.5) H10C(0.5) C10B(0.5) H10D(0.5) H10E(0.5) H10F(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C4B(H4B), C5(H5), C5B(H5B), C7(H7), C7B(H7B), C8(H8), C8B(H8B),
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
3.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C9B(H9BA,H9BB,H9BC), C10(H10A,H10B,H10C), C10B(H10D,H10E,
 H10F), C12(H12A,H12B,H12C)
;
_contact_crystallographer_email  staples@chemistry.msu.com
_contact_crystallographer_name   'Richard Staples'
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id BH01917
_olex2_submission_special_instructions 'No special instructions were received'