The enhancement of the D‒A effect of an asymmetric Schiff base by introducing acetyl groups into diaminomaleonitrile: synthesis, red fluorescence and crystal structure
Wang, Ke; Su, Hao; Wang, Pengfei; Wang, Wenjie; Li, Hui; RSC Advances 9 (2019) 14268–; doi:10.1039/C9RA00977A

data_7232728
_publ_section_title
;
 The enhancement of the D--A effect of an asymmetric Schiff base by
 introducing acetyl groups into diaminomaleonitrile: synthesis, red
 fluorescence and crystal structure
;
_journal_issue                   25
_journal_name_full               'RSC Advances'
_journal_page_first              14268
_journal_paper_doi               10.1039/C9RA00977A
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C13.5 H11 N4 O3 Zn'
_chemical_formula_sum            'C13.5 H11 N4 O3 Zn'
_chemical_formula_weight         342.63
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-07-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-08-19 deposited with the CCDC.    2019-04-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.578(11)
_cell_length_b                   8.180(5)
_cell_length_c                   10.632(7)
_cell_measurement_reflns_used    3549
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.10
_cell_measurement_theta_min      2.24
_cell_volume                     1528.8(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12905
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.024
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         1.915
_exptl_absorpt_coefficient_mu    1.622
_exptl_absorpt_correction_T_max  0.8545
_exptl_absorpt_correction_T_min  0.6416
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.929
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.113
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.10(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2699
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0476
_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^)+(0.0745P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1282
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2142
_reflns_number_total             2699
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra00977a2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_formula_sum        'C13.50 H11 N4 O3 Zn'
_cod_database_code               7232728
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.855
_shelx_estimated_absorpt_t_min   0.642
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.90(4)
 0.10(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
3. Others
 Fixed Sof: H2A(0.5) C15(0.5) H15A(0.5) H15B(0.5) H15C(0.5)
4.a Riding coordinates:
 O2(H2A,H2B)
4.b Me refined with riding coordinates:
 C9(H9A,H9B,H9C)
4.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C3(H3), C6(H6), C2(H2)
4.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              47234
_olex2_submission_special_instructions 'No special instructions were received'