White-Light Emission from a Structurally Simple Hydrazone
Shao, Baihao; Stankewitz, Nell; Morris, Jacob A.; Liptak, Matthew D.; Aprahamian, Ivan; Chemical Communications  (2019) –; doi:10.1039/C9CC03912K

data_7123895
_publ_section_title
;
 White-Light Emission from a Structurally Simple Hydrazone
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC03912K
_journal_year                    2019
_chemical_formula_moiety         'C22 H23 N3 O2'
_chemical_formula_sum            'C22 H23 N3 O2'
_chemical_formula_weight         361.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-16
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-06-23 deposited with the CCDC.    2019-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.827(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8408(14)
_cell_length_b                   7.6010(11)
_cell_length_c                   25.340(4)
_cell_measurement_reflns_used    9800
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.28
_cell_measurement_theta_min      2.56
_cell_volume                     1893.1(5)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            28100
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.400
_diffrn_reflns_theta_min         1.609
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0686 before and 0.0635 after correction. The Ratio of minimum to maximum transmission is 0.9202. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       chunk
_exptl_crystal_F_000             768
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.346
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.207
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         3462
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0429
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0654P)^2^+0.3101P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1246
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2719
_reflns_number_total             3462
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc03912k2.cif
_cod_data_source_block           ia1017e
_cod_database_code               7123895
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.972
_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
2. Restrained distances
 C11-N2A \\sim C11B-N2
 with sigma of 0.02
 N1-N2 \\sim N1-N2A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C13B) = Uanis(C14)
Uanis(N2A) = Uanis(N2)
Uanis(C21) = Uanis(C22B)
4. Others
 Sof(N2)=Sof(H2)=Sof(N3B)=Sof(C11B)=Sof(C12B)=Sof(H12B)=Sof(C13B)=Sof(C14B)=
 Sof(H14B)=Sof(C15B)=Sof(H15B)=Sof(C16B)=Sof(C17B)=Sof(H17B)=Sof(C18B)=
 Sof(C19B)=Sof(H19B)=Sof(C20B)=Sof(H20B)=Sof(C21B)=Sof(H21D)=Sof(H21E)=
 Sof(H21F)=Sof(C22B)=Sof(H22D)=Sof(H22E)=Sof(H22F)=1-FVAR(1)
 Sof(N2A)=Sof(H2A)=Sof(N3)=Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=
 Sof(C14)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=
 Sof(C19)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C22)=
 Sof(H22A)=Sof(H22B)=Sof(H22C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N2A(H2A), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12),
 C12B(H12B), C13(H13), C14B(H14B), C15(H15), C15B(H15B), C17(H17), C17B(H17B),
 C18(H18), C19B(H19B), C20(H20), C20B(H20B)
5.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C21(H21A,H21B,H21C), C21B(H21D,H21E,H21F), C22(H22A,H22B,
 H22C), C22B(H22D,H22E,H22F)
;
_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 BHS-NapNCH3
_olex2_submission_special_instructions 'No special instructions were received'