#------------------------------------------------------------------------------
#$Date: 2019-11-15 10:12:34 +0200 (Fri, 15 Nov 2019) $
#$Revision: 227870 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/51/7235115.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_7235115
loop_
_publ_author_name
'Ting Han'
'Xinggui Gu'
'Jacky W. Y. Lam'
'Anakin C. S. Leung'
'Ryan T. K. Kwok'
'Tianyu Han'
'Bin Tong'
'Jianbing Shi'
'Yuping Dong'
'Ben Zhong Tang'
_publ_section_title
;
 Diaminomaleonitrile-based Schiff bases: aggregation-enhanced emission,
 red fluorescence, mechanochromism and bioimaging applications
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              10430
_journal_page_last               10434
_journal_paper_doi               10.1039/C6TC03883B
_journal_volume                  4
_journal_year                    2016
_chemical_formula_moiety         'C19 H25 N5'
_chemical_formula_sum            'C19 H25 N5'
_chemical_formula_weight         323.44
_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'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 98.363(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.594(3)
_cell_length_b                   13.655(3)
_cell_length_c                   20.363(4)
_cell_measurement_reflns_used    13635
_cell_measurement_temperature    153.1500
_cell_measurement_theta_max      31.4970
_cell_measurement_theta_min      1.8017
_cell_volume                     3739.7(14)
_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      153.15
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            30554
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.343
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         7273
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0545
_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)+(0.0860P)²+1.0690P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1516
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6355
_reflns_number_total             7273
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            J-Mater-Chem-C-2016-4-10430.cif
_cod_data_source_block           ht-ding
_cod_original_cell_volume        3739.5(13)
_cod_database_code               7235115
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.17056(10) 0.37782(9) 0.20371(6) 0.0261(3) Uani 1 1 d . . . . .
N2 N 0.13406(11) 0.20352(10) 0.26955(8) 0.0341(3) Uani 1 1 d . . . . .
H2A H 0.1938 0.2120 0.2587 0.041 Uiso 1 1 calc R . . . .
H2B H 0.1196 0.1489 0.2890 0.041 Uiso 1 1 calc R . . . .
N3 N -0.05125(11) 0.50073(11) 0.21336(8) 0.0396(4) Uani 1 1 d . . . . .
N4 N -0.10512(12) 0.24223(12) 0.29660(9) 0.0468(4) Uani 1 1 d . . . . .
N5 N 0.55338(10) 0.56512(10) 0.09386(7) 0.0306(3) Uani 1 1 d . . . . .
C1 C 0.08000(12) 0.36183(11) 0.22628(8) 0.0263(3) Uani 1 1 d . . . . .
C2 C 0.06433(12) 0.27454(11) 0.25634(8) 0.0275(3) Uani 1 1 d . . . . .
C3 C 0.00453(12) 0.43661(12) 0.22042(8) 0.0284(3) Uani 1 1 d . . . . .
C4 C -0.03040(13) 0.25705(12) 0.27871(9) 0.0325(4) Uani 1 1 d . . . . .
C5 C 0.46508(12) 0.53965(11) 0.11401(8) 0.0262(3) Uani 1 1 d . . . . .
C6 C 0.44425(12) 0.44099(11) 0.12989(8) 0.0274(3) Uani 1 1 d . . . . .
H6 H 0.4922 0.3916 0.1258 0.033 Uiso 1 1 calc R . . . .
C7 C 0.35599(12) 0.41591(11) 0.15099(8) 0.0275(3) Uani 1 1 d . . . . .
H7 H 0.3445 0.3495 0.1615 0.033 Uiso 1 1 calc R . . . .
C8 C 0.28232(12) 0.48611(11) 0.15731(8) 0.0263(3) Uani 1 1 d . . . . .
C9 C 0.30209(12) 0.58321(12) 0.14056(8) 0.0297(4) Uani 1 1 d . . . . .
H9 H 0.2532 0.6321 0.1437 0.036 Uiso 1 1 calc R . . . .
C10 C 0.39017(12) 0.60955(11) 0.11971(8) 0.0291(4) Uani 1 1 d . . . . .
H10 H 0.4008 0.6760 0.1089 0.035 Uiso 1 1 calc R . . . .
C11 C 0.19056(12) 0.46319(11) 0.18178(8) 0.0276(3) Uani 1 1 d . . . . .
H11 H 0.1423 0.5136 0.1818 0.033 Uiso 1 1 calc R . . . .
C12 C 0.58611(12) 0.66703(12) 0.09152(8) 0.0287(3) Uani 1 1 d . . . . .
H12C H 0.6588 0.6699 0.1060 0.034 Uiso 1 1 calc R . . . .
H12D H 0.5537 0.7060 0.1233 0.034 Uiso 1 1 calc R . . . .
C13 C 0.56262(12) 0.71303(12) 0.02300(8) 0.0301(4) Uani 1 1 d . . . . .
H13C H 0.4901 0.7088 0.0079 0.036 Uiso 1 1 calc R . . . .
H13D H 0.5967 0.6754 -0.0086 0.036 Uiso 1 1 calc R . . . .
C14 C 0.59485(14) 0.82006(13) 0.02206(9) 0.0373(4) Uani 1 1 d . . . . .
H14C H 0.5624 0.8575 0.0546 0.045 Uiso 1 1 calc R . . . .
H14D H 0.6677 0.8243 0.0356 0.045 Uiso 1 1 calc R . . . .
C15 C 0.56787(18) 0.86576(17) -0.04643(11) 0.0547(6) Uani 1 1 d . . . . .
H15D H 0.5993 0.8284 -0.0789 0.082 Uiso 1 1 calc GR . . . .
H15E H 0.5914 0.9336 -0.0454 0.082 Uiso 1 1 calc GR . . . .
H15F H 0.4955 0.8646 -0.0591 0.082 Uiso 1 1 calc GR . . . .
C16 C 0.62298(12) 0.49083(12) 0.07727(9) 0.0316(4) Uani 1 1 d . . . . .
H16E H 0.6619 0.5184 0.0442 0.038 Uiso 1 1 calc R . . . .
H16F H 0.5847 0.4344 0.0564 0.038 Uiso 1 1 calc R . . . .
C17 C 0.69495(13) 0.45415(13) 0.13700(9) 0.0355(4) Uani 1 1 d . . . . .
H17E H 0.7447 0.5057 0.1512 0.043 Uiso 1 1 calc R . . . .
H17F H 0.6576 0.4413 0.1744 0.043 Uiso 1 1 calc R . . . .
C18 C 0.74857(15) 0.36074(13) 0.12106(10) 0.0420(5) Uani 1 1 d . . . . .
H18E H 0.7923 0.3390 0.1616 0.050 Uiso 1 1 calc R . . . .
H18F H 0.6985 0.3087 0.1088 0.050 Uiso 1 1 calc R . . . .
C19 C 0.81060(17) 0.37178(16) 0.06547(12) 0.0552(6) Uani 1 1 d . . . . .
H19G H 0.7680 0.3929 0.0250 0.083 Uiso 1 1 calc GR . . . .
H19H H 0.8414 0.3088 0.0575 0.083 Uiso 1 1 calc GR . . . .
H19I H 0.8626 0.4208 0.0779 0.083 Uiso 1 1 calc GR . . . .
N1A N 0.33017(10) 0.57545(10) 0.32019(7) 0.0288(3) Uani 1 1 d . . . . .
N2A N 0.42668(12) 0.73271(10) 0.27762(8) 0.0396(4) Uani 1 1 d . . . . .
H2AA H 0.3666 0.7402 0.2882 0.048 Uiso 1 1 calc R . . . .
H2AB H 0.4583 0.7833 0.2639 0.048 Uiso 1 1 calc R . . . .
N3A N 0.50762(12) 0.39119(11) 0.31342(8) 0.0389(4) Uani 1 1 d . . . . .
N4A N 0.65239(12) 0.63968(13) 0.25906(8) 0.0434(4) Uani 1 1 d . . . . .
N5A N -0.09852(10) 0.57556(10) 0.41673(7) 0.0306(3) Uani 1 1 d . . . . .
C1A C 0.42471(12) 0.56201(11) 0.30358(8) 0.0267(3) Uani 1 1 d . . . . .
C2A C 0.47067(12) 0.64302(12) 0.28247(8) 0.0294(4) Uani 1 1 d . . . . .
C3A C 0.47366(12) 0.46857(12) 0.30846(8) 0.0297(4) Uani 1 1 d . . . . .
C4A C 0.57146(13) 0.63826(12) 0.26858(8) 0.0323(4) Uani 1 1 d . . . . .
C5A C -0.00895(12) 0.55685(12) 0.39625(8) 0.0267(3) Uani 1 1 d . . . . .
C6A C 0.04930(12) 0.63344(12) 0.37473(8) 0.0290(4) Uani 1 1 d . . . . .
H6A H 0.0243 0.6985 0.3730 0.035 Uiso 1 1 calc R . . . .
C7A C 0.14068(12) 0.61572(12) 0.35641(8) 0.0289(4) Uani 1 1 d . . . . .
H7A H 0.1774 0.6689 0.3421 0.035 Uiso 1 1 calc R . . . .
C8A C 0.18169(12) 0.52088(11) 0.35818(8) 0.0266(3) Uani 1 1 d . . . . .
C9A C 0.12446(12) 0.44488(11) 0.37892(8) 0.0276(3) Uani 1 1 d . . . . .
H9A H 0.1501 0.3801 0.3806 0.033 Uiso 1 1 calc R . . . .
C10A C 0.03183(12) 0.46127(12) 0.39706(8) 0.0278(3) Uani 1 1 d . . . . .
H10A H -0.0052 0.4076 0.4103 0.033 Uiso 1 1 calc R . . . .
C11A C 0.27905(12) 0.50393(12) 0.33965(8) 0.0273(3) Uani 1 1 d . . . . .
H11A H 0.3058 0.4395 0.3418 0.033 Uiso 1 1 calc R . . . .
C12A C -0.15483(12) 0.49675(12) 0.44246(8) 0.0304(4) Uani 1 1 d . . . . .
H12A H -0.1995 0.5254 0.4716 0.036 Uiso 1 1 calc R . . . .
H12B H -0.1079 0.4525 0.4699 0.036 Uiso 1 1 calc R . . . .
C13A C -0.21687(13) 0.43671(13) 0.38823(8) 0.0324(4) Uani 1 1 d . . . . .
H13A H -0.2757 0.4754 0.3690 0.039 Uiso 1 1 calc R . . . .
H13B H -0.1768 0.4231 0.3524 0.039 Uiso 1 1 calc R . . . .
C14A C -0.25133(14) 0.34028(13) 0.41467(10) 0.0394(4) Uani 1 1 d . . . . .
H14A H -0.2907 0.3042 0.3776 0.047 Uiso 1 1 calc R . . . .
H14B H -0.1922 0.3001 0.4310 0.047 Uiso 1 1 calc R . . . .
C15A C -0.31364(15) 0.35174(14) 0.47032(10) 0.0445(5) Uani 1 1 d . . . . .
H15A H -0.2752 0.3869 0.5074 0.067 Uiso 1 1 calc GR . . . .
H15B H -0.3319 0.2869 0.4853 0.067 Uiso 1 1 calc GR . . . .
H15C H -0.3741 0.3888 0.4541 0.067 Uiso 1 1 calc GR . . . .
C16A C -0.1546(2) 0.6669(2) 0.40219(16) 0.0306(7) Uiso 0.6667 1 d D . P A 1
H16A H -0.2240 0.6502 0.3836 0.037 Uiso 0.6667 1 calc R . P A 1
H16B H -0.1255 0.7031 0.3675 0.037 Uiso 0.6667 1 calc R . P A 1
C16B C -0.1344(5) 0.6768(4) 0.4197(3) 0.0327(15) Uiso 0.3333 1 d D . P A 2
H16C H -0.2075 0.6762 0.4183 0.039 Uiso 0.3333 1 calc R . P A 2
H16D H -0.1192 0.7131 0.3803 0.039 Uiso 0.3333 1 calc R . P A 2
C17A C -0.1564(2) 0.7348(2) 0.46191(14) 0.0391(6) Uiso 0.6667 1 d D . P A 1
H17A H -0.2070 0.7863 0.4497 0.047 Uiso 0.6667 1 calc R . P A 1
H17B H -0.1772 0.6964 0.4988 0.047 Uiso 0.6667 1 calc R . P A 1
C17B C -0.0886(4) 0.7279(4) 0.4804(3) 0.0328(11) Uiso 0.3333 1 d D . P A 2
H17C H -0.0159 0.7166 0.4866 0.039 Uiso 0.3333 1 calc R . P A 2
H17D H -0.1148 0.6995 0.5191 0.039 Uiso 0.3333 1 calc R . P A 2
C18A C -0.0578(2) 0.7835(3) 0.48631(16) 0.0477(7) Uiso 0.6667 1 d D . P A 1
H18A H -0.0369 0.8235 0.4502 0.057 Uiso 0.6667 1 calc R . P A 1
H18B H -0.0065 0.7327 0.4988 0.057 Uiso 0.6667 1 calc R . P A 1
C18B C -0.1082(6) 0.8374(5) 0.4783(4) 0.0650(19) Uiso 0.3333 1 d D . P A 2
H18C H -0.0897 0.8650 0.4369 0.078 Uiso 0.3333 1 calc R . P A 2
H18D H -0.1799 0.8496 0.4785 0.078 Uiso 0.3333 1 calc R . P A 2
C19A C -0.0664(4) 0.8506(4) 0.5481(3) 0.0833(15) Uiso 0.6667 1 d D . P A 1
H19A H -0.0776 0.8097 0.5858 0.125 Uiso 0.6667 1 calc GR . P A 1
H19B H -0.1223 0.8959 0.5372 0.125 Uiso 0.6667 1 calc GR . P A 1
H19C H -0.0048 0.8879 0.5596 0.125 Uiso 0.6667 1 calc GR . P A 1
C19B C -0.0488(10) 0.8876(10) 0.5374(6) 0.103(4) Uiso 0.3333 1 d D . P A 2
H19D H -0.0328 0.9545 0.5251 0.154 Uiso 0.3333 1 calc GR . P A 2
H19E H 0.0128 0.8512 0.5512 0.154 Uiso 0.3333 1 calc GR . P A 2
H19F H -0.0881 0.8897 0.5741 0.154 Uiso 0.3333 1 calc GR . P A 2
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'
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
C11 N1 C1 119.76(13) . .
C5 N5 C12 122.37(13) . .
C5 N5 C16 121.26(13) . .
C16 N5 C12 116.27(13) . .
N1 C1 C3 120.99(14) . .
C2 C1 N1 119.09(14) . .
C2 C1 C3 119.89(15) . .
N2 C2 C1 124.14(15) . .
N2 C2 C4 116.62(14) . .
C1 C2 C4 119.17(15) . .
N3 C3 C1 174.89(18) . .
N4 C4 C2 179.3(2) . .
N5 C5 C6 121.38(14) . .
N5 C5 C10 121.80(14) . .
C10 C5 C6 116.81(14) . .
C7 C6 C5 121.20(14) . .
C6 C7 C8 121.63(14) . .
C7 C8 C11 123.15(14) . .
C9 C8 C7 117.22(14) . .
C9 C8 C11 119.60(14) . .
C10 C9 C8 121.85(15) . .
C9 C10 C5 121.27(15) . .
N1 C11 C8 123.45(14) . .
N5 C12 C13 113.46(13) . .
C12 C13 C14 112.61(14) . .
C15 C14 C13 111.85(16) . .
N5 C16 C17 113.85(14) . .
C18 C17 C16 111.97(15) . .
C19 C18 C17 114.25(16) . .
C11A N1A C1A 122.18(14) . .
C5A N5A C12A 120.53(14) . .
C5A N5A C16A 123.78(16) . .
C5A N5A C16B 120.3(3) . .
C12A N5A C16A 114.46(17) . .
C12A N5A C16B 118.9(3) . .
N1A C1A C3A 122.47(14) . .
C2A C1A N1A 116.77(14) . .
C2A C1A C3A 120.76(15) . .
N2A C2A C1A 122.28(15) . .
N2A C2A C4A 116.57(14) . .
C1A C2A C4A 121.03(15) . .
N3A C3A C1A 175.78(18) . .
N4A C4A C2A 176.11(19) . .
N5A C5A C6A 121.21(15) . .
N5A C5A C10A 122.19(14) . .
C10A C5A C6A 116.58(14) . .
C7A C6A C5A 121.53(15) . .
C6A C7A C8A 121.80(15) . .
C7A C8A C11A 120.95(14) . .
C9A C8A C7A 117.03(15) . .
C9A C8A C11A 122.02(15) . .
C10A C9A C8A 121.97(15) . .
C9A C10A C5A 121.09(14) . .
N1A C11A C8A 120.77(15) . .
N5A C12A C13A 113.51(14) . .
C14A C13A C12A 112.00(15) . .
C15A C14A C13A 114.12(15) . .
N5A C16A C17A 114.9(2) . .
N5A C16B C17B 112.1(5) . .
C18A C17A C16A 114.2(3) . .
C16B C17B C18B 113.0(5) . .
C17A C18A C19A 110.6(3) . .
C19B C18B C17B 110.7(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.392(2) .
N1 C11 1.291(2) .
N2 C2 1.355(2) .
N3 C3 1.153(2) .
N4 C4 1.146(2) .
N5 C5 1.369(2) .
N5 C12 1.464(2) .
N5 C16 1.460(2) .
C1 C2 1.371(2) .
C1 C3 1.440(2) .
C2 C4 1.447(2) .
C5 C6 1.424(2) .
C5 C10 1.413(2) .
C6 C7 1.375(2) .
C7 C8 1.406(2) .
C8 C9 1.405(2) .
C8 C11 1.443(2) .
C9 C10 1.375(2) .
C12 C13 1.521(2) .
C13 C14 1.527(2) .
C14 C15 1.523(3) .
C16 C17 1.530(2) .
C17 C18 1.527(2) .
C18 C19 1.514(3) .
N1A C1A 1.388(2) .
N1A C11A 1.294(2) .
N2A C2A 1.360(2) .
N3A C3A 1.152(2) .
N4A C4A 1.145(2) .
N5A C5A 1.367(2) .
N5A C12A 1.461(2) .
N5A C16A 1.470(3) .
N5A C16B 1.470(6) .
C1A C2A 1.370(2) .
C1A C3A 1.436(2) .
C2A C4A 1.440(2) .
C5A C6A 1.419(2) .
C5A C10A 1.417(2) .
C6A C7A 1.369(2) .
C7A C8A 1.408(2) .
C8A C9A 1.399(2) .
C8A C11A 1.447(2) .
C9A C10A 1.381(2) .
C12A C13A 1.527(2) .
C13A C14A 1.522(2) .
C14A C15A 1.518(3) .
C16A C17A 1.532(4) .
C16B C17B 1.477(8) .
C17A C18A 1.515(4) .
C17B C18B 1.519(9) .
C18A C19A 1.574(6) .
C18B C19B 1.511(12) .
