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_7232729
_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         'C51 H52 N15 O7 Zn3, C6 H16 N, O'
_chemical_formula_sum            'C57 H68 N16 O8 Zn3'
_chemical_formula_weight         1301.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2018-05-15
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2018-08-19 deposited with the CCDC.    2019-04-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.368(5)
_cell_angle_beta                 96.639(5)
_cell_angle_gamma                101.761(5)
_cell_formula_units_Z            2
_cell_length_a                   12.456(2)
_cell_length_b                   13.244(2)
_cell_length_c                   19.423(3)
_cell_measurement_reflns_used    2192
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22
_cell_measurement_theta_min      2
_cell_volume                     3114.4(8)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_unetI/netI     0.0966
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            29215
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.482
_diffrn_reflns_theta_min         1.571
_exptl_absorpt_coefficient_mu    1.211
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       block
_exptl_crystal_F_000             1352
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.980
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     779
_refine_ls_number_reflns         11379
_refine_ls_number_restraints     194
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0571
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0735P)^2^+1.6672P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1662
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7062
_reflns_number_total             11379
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra00977a2.cif
_cod_data_source_block           1_CCDC1
_cod_original_cell_volume        3114.3(9)
_cod_database_code               7232729
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.889
_shelx_estimated_absorpt_t_min   0.752
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C96-N23 = N23-C92
 1.4 with sigma of 0.02
 C94-N23
 1.4 with sigma of 0.02
 C95-C94 = C97-C96 = C93-C92
 1.5 with sigma of 0.01
 C92-C96
 2.4 with sigma of 0.02
 H96A-H92A
 2.2 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C8) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C47) \\sim
Ueq, Uanis(N1) \\sim Ueq, Uanis(C53) \\sim Ueq, Uanis(C52) \\sim Ueq, Uanis(N2)
\\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(O31) \\sim Ueq, Uanis(O31A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C8, C7, N1, C9, C47, C5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C19, C18, N2, C15, C52, C53
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N10, C54, O8, C55
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N23, C94, C92, C96, C95, C93, C97
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O31
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(O31A)=1-FVAR(1)
 Sof(O31)=FVAR(1)
 Fixed Sof: O8(0.5) O8A(0.5)
6.a Riding coordinates:
 O10(H10)
6.b Ternary CH refined with riding coordinates:
 N23(H23)
6.c Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C35(H35A,H35B), C37(H37A,H37B), C9(H9A,H9B), C7(H7A,H7B),
 C52(H52A,H52B), C94(H94A,H94B), C92(H92A,H92B), C96(H96A,H96B)
6.d Me refined with riding coordinates:
 C40(H40A,H40B,H40C), C25(H25A,H25B,H25C), C36(H36A,H36B,H36C), C19(H19A,H19B,
 H19C), C38(H38A,H38B,H38C), C8(H8A,H8B,H8C), C47(H47A,H47B,H47C), C55(H55A,
 H55B,H55C), C53(H53A,H53B,H53C)
6.e Aromatic/amide H refined with riding coordinates:
 C29(H29), C10(H10A), C34(H34), C26(H26), C31(H31), C27(H27), C32(H32), C2(H2),
  C3(H3), C13(H13), C6(H6), C14(H14)
6.f Idealised Me refined as rotating group:
 C93(H93A,H93B,H93C), C97(H97A,H97B,H97C), C95(H95A,H95B,H95C)
;
_shelx_res_checksum              20457
_olex2_submission_special_instructions 'No special instructions were received'