#------------------------------------------------------------------------------
#$Date: 2019-05-09 04:39:04 +0300 (Thu, 09 May 2019) $
#$Revision: 215004 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/27/7232728.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7232728
loop_
_publ_author_name
'Wang, Ke'
'Su, Hao'
'Wang, Pengfei'
'Wang, Wenjie'
'Li, Hui'
_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/[σ²(Fo²)+(0.0745P)²] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.0753(3) 0.5964(8) -0.0183(6) 0.0636(18) Uani 1 1 d . . . .
H2A H 0.040732 0.556493 -0.060102 0.095 Uiso 0.5 1 d R P A -2
H2B H 0.045952 0.654033 0.037388 0.095 Uiso 1 1 d R . B .
Zn1 Zn 0.13568(5) 0.43984(11) 0.09166(8) 0.0428(3) Uani 1 1 d . . . .
O3 O 0.3204(3) 0.7766(7) 0.0276(5) 0.0513(15) Uani 1 1 d . . . .
O1 O 0.0402(3) 0.3103(7) 0.1257(5) 0.0526(15) Uani 1 1 d . . . .
N1 N 0.1497(3) 0.4607(8) 0.2842(6) 0.0409(15) Uani 1 1 d . . . .
N2 N 0.2362(3) 0.5861(8) 0.0996(6) 0.0467(15) Uani 1 1 d . . . .
N3 N 0.2476(5) 0.6024(14) 0.5473(8) 0.088(3) Uani 1 1 d . . . .
N4 N 0.3716(6) 0.7841(15) 0.3021(8) 0.105(4) Uani 1 1 d . . . .
C13 C 0.2721(4) 0.6667(10) 0.0058(7) 0.0419(19) Uani 1 1 d . . . .
C14 C 0.2126(4) 0.5511(10) 0.3169(7) 0.0424(18) Uani 1 1 d . . . .
C11 C 0.2553(4) 0.6169(10) 0.2243(7) 0.0426(19) Uani 1 1 d . . . .
C10 C 0.1055(5) 0.3995(9) 0.3719(8) 0.046(2) Uani 1 1 d . . . .
H10 H 0.119576 0.418369 0.454922 0.055 Uiso 1 1 calc R . . .
C4 C 0.0085(5) 0.2662(10) 0.2309(8) 0.046(2) Uani 1 1 d . . . .
C12 C -0.0595(5) 0.1709(10) 0.2251(10) 0.058(2) Uani 1 1 d . . . .
H12 H -0.079871 0.140677 0.147808 0.070 Uiso 1 1 calc R . . .
C5 C 0.0385(5) 0.3077(10) 0.3521(8) 0.048(2) Uani 1 1 d . . . .
C7 C 0.3213(5) 0.7101(13) 0.2621(8) 0.062(3) Uani 1 1 d . . . .
C8 C 0.2325(5) 0.5798(12) 0.4456(7) 0.055(2) Uani 1 1 d . . . .
C3 C -0.0952(6) 0.1234(12) 0.3377(13) 0.073(3) Uani 1 1 d . . . .
H3 H -0.139647 0.061979 0.333241 0.088 Uiso 1 1 calc R . . .
C6 C -0.0005(6) 0.2592(14) 0.4618(9) 0.068(3) Uani 1 1 d . . . .
H6 H 0.017760 0.290183 0.540383 0.082 Uiso 1 1 calc R . . .
C9 C 0.2535(7) 0.6196(13) -0.1242(8) 0.081(4) Uani 1 1 d . . . .
H9A H 0.215765 0.534721 -0.123299 0.122 Uiso 1 1 calc R . . .
H9B H 0.233992 0.712844 -0.168599 0.122 Uiso 1 1 calc R . . .
H9C H 0.298513 0.580598 -0.165478 0.122 Uiso 1 1 calc R . . .
C2 C -0.0672(6) 0.1637(14) 0.4524(11) 0.079(3) Uani 1 1 d . . . .
H2 H -0.091950 0.128464 0.524891 0.095 Uiso 1 1 calc R . . .
C15 C 0.0581(17) 0.583(4) -0.166(3) 0.141(13) Uani 0.5 1 d . P B -1
H15A H 0.100706 0.534084 -0.207444 0.211 Uiso 0.5 1 calc GR P B -1
H15B H 0.049594 0.690780 -0.199319 0.211 Uiso 0.5 1 calc GR P B -1
H15C H 0.013565 0.517514 -0.178770 0.211 Uiso 0.5 1 calc GR P B -1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
H2A O2 H2B 98.0 . .
Zn1 O2 H2A 116.6 . .
Zn1 O2 H2B 104.3 . .
C15 O2 H2B 124.1 . .
C15 O2 Zn1 128.3(12) . .
O2 Zn1 N1 125.4(3) . .
O2 Zn1 N2 95.8(3) . .
O3 Zn1 O2 105.0(3) 4_545 .
O3 Zn1 O1 94.8(2) 4_545 .
O3 Zn1 N1 129.6(2) 4_545 .
O3 Zn1 N2 94.6(2) 4_545 .
O1 Zn1 O2 90.0(2) . .
O1 Zn1 N1 88.0(2) . .
O1 Zn1 N2 167.3(2) . .
N1 Zn1 N2 79.4(2) . .
C13 O3 Zn1 128.4(5) . 4
C4 O1 Zn1 131.0(5) . .
C14 N1 Zn1 113.0(5) . .
C10 N1 Zn1 126.9(5) . .
C10 N1 C14 120.1(7) . .
C13 N2 Zn1 129.1(5) . .
C13 N2 C11 120.2(7) . .
C11 N2 Zn1 109.8(5) . .
O3 C13 N2 121.8(7) . .
O3 C13 C9 120.7(7) . .
N2 C13 C9 117.5(7) . .
N1 C14 C8 121.8(7) . .
C11 C14 N1 118.5(7) . .
C11 C14 C8 119.7(7) . .
N2 C11 C7 123.7(7) . .
C14 C11 N2 119.3(7) . .
C14 C11 C7 117.0(7) . .
N1 C10 H10 116.9 . .
N1 C10 C5 126.2(8) . .
C5 C10 H10 116.9 . .
O1 C4 C12 118.2(8) . .
O1 C4 C5 123.3(7) . .
C12 C4 C5 118.4(8) . .
C4 C12 H12 120.4 . .
C3 C12 C4 119.2(9) . .
C3 C12 H12 120.4 . .
C10 C5 C4 124.6(8) . .
C6 C5 C10 115.5(8) . .
C6 C5 C4 119.9(8) . .
N4 C7 C11 174.4(10) . .
N3 C8 C14 179.4(10) . .
C12 C3 H3 118.8 . .
C2 C3 C12 122.5(9) . .
C2 C3 H3 118.8 . .
C5 C6 H6 120.0 . .
C5 C6 C2 120.0(10) . .
C2 C6 H6 120.0 . .
C13 C9 H9A 109.5 . .
C13 C9 H9B 109.5 . .
C13 C9 H9C 109.5 . .
H9A C9 H9B 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C3 C2 C6 119.9(9) . .
C3 C2 H2 120.0 . .
C6 C2 H2 120.0 . .
O2 C15 H15A 109.5 . .
O2 C15 H15B 109.5 . .
O2 C15 H15C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 H2A 0.8202 .
O2 H2B 0.9156 .
O2 Zn1 2.033(6) .
O2 C15 1.60(3) .
Zn1 O3 1.996(6) 4_545
Zn1 O1 2.017(6) .
Zn1 N1 2.069(6) .
Zn1 N2 2.136(6) .
O3 C13 1.259(10) .
O1 C4 1.301(9) .
N1 C14 1.375(9) .
N1 C10 1.313(10) .
N2 C13 1.351(10) .
N2 C11 1.391(10) .
N3 C8 1.128(9) .
N4 C7 1.153(11) .
C13 C9 1.471(12) .
C14 C11 1.350(10) .
C14 C8 1.432(11) .
C11 C7 1.445(11) .
C10 H10 0.9300 .
C10 C5 1.412(11) .
C4 C12 1.428(12) .
C4 C5 1.433(12) .
C12 H12 0.9300 .
C12 C3 1.407(13) .
C5 C6 1.410(12) .
C3 H3 0.9300 .
C3 C2 1.356(15) .
C6 H6 0.9300 .
C6 C2 1.414(15) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C2 H2 0.9300 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.90(4)
2 0.10(4)
