#------------------------------------------------------------------------------
#$Date: 2016-03-21 15:20:55 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178744 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/55/4085536.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_4085536
loop_
_publ_author_name
'Evans, Daniel A.'
'Lee, Lucia Myongwon'
'Vargas-Baca, Ignacio'
'Cowley, Alan H.'
_publ_section_title
;
 Aggregation-Induced Emission of Bis(imino)acenaphthene Zinc Complexes:
 Photophysical Tuning via Methylation of the Flanking Aryl Substituents
;
_journal_issue                   11
_journal_name_full               Organometallics
_journal_page_first              2422
_journal_paper_doi               10.1021/om501191c
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C26 H20 Cl2 N2 Zn, 2(C H Cl3)'
_chemical_formula_sum            'C28 H22 Cl8 N2 Zn'
_chemical_formula_weight         735.44
_chemical_name_systematic
;
 ?
;
_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
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 98.4180(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.80690(10)
_cell_length_b                   23.7064(3)
_cell_length_c                   11.05040(10)
_cell_measurement_reflns_used    8236
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      73.9680
_cell_measurement_theta_min      3.7870
_cell_volume                     3059.67(5)
_computing_cell_refinement
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_data_collection
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_data_reduction
'CrysAlisPro V 1.171.37.31, Agilent Technologies'
_computing_molecular_graphics    'XP SHELXTL/PC, Siemens Analytical'
_computing_publication_material  'XL SHELXTL/PC, Siemens Analytical'
_computing_structure_refinement  'Shelxl-2013, Sheldrick, G. M.'
_computing_structure_solution
;

SUPERFLIP.  Palatinus, L. and Chapuis, G., J. Appl. Cryst. 40, 786-790.
;
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Agilent SuperNova with AtlasS2 detector'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12057
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.163
_diffrn_reflns_theta_min         3.729
_diffrn_source                   'sealed X-ray source'
_exptl_absorpt_coefficient_mu    7.725
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_description       prism
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         6064
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0330
_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/[σ²(Fo²)+(0.0483P)²+1.9267P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0931
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5668
_reflns_number_total             6064
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om501191c_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 4085532--4085543.cif.'
_cod_database_code               4085536
#BEGIN Tags that were not found in dictionaries:
_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_min   0.179
_shelx_estimated_absorpt_t_max   0.307
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
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
Zn1 Zn 0.37225(2) 0.57842(2) 0.38881(2) 0.01138(8) Uani 1 1 d . .
Cl2 Cl 0.27811(4) 0.65086(2) 0.29260(5) 0.01798(12) Uani 1 1 d . .
Cl1 Cl 0.55773(4) 0.57067(2) 0.38977(5) 0.02153(12) Uani 1 1 d . .
Cl7 Cl 0.43139(5) 0.27221(3) 0.70578(5) 0.02833(14) Uani 1 1 d . .
Cl6 Cl 0.31435(6) 0.28516(3) 0.45870(5) 0.03054(14) Uani 1 1 d . .
Cl8 Cl 0.18484(5) 0.27064(3) 0.65868(6) 0.03186(15) Uani 1 1 d . .
Cl4 Cl -0.01641(6) 0.69951(3) 0.12060(6) 0.03555(16) Uani 1 1 d . .
Cl3 Cl 0.03585(9) 0.60970(3) -0.03762(7) 0.0497(2) Uani 1 1 d . .
Cl5 Cl 0.09699(6) 0.72438(3) -0.08839(7) 0.03645(16) Uani 1 1 d . .
N1 N 0.28691(14) 0.50253(7) 0.34401(15) 0.0115(3) Uani 1 1 d . .
N2 N 0.30650(14) 0.56502(7) 0.55113(15) 0.0110(3) Uani 1 1 d . .
C6 C 0.02330(17) 0.41848(8) 0.59857(19) 0.0144(4) Uani 1 1 d . .
C7 C 0.11008(16) 0.45074(8) 0.55619(18) 0.0114(4) Uani 1 1 d . .
C9 C 0.03606(18) 0.48281(10) 0.7707(2) 0.0182(4) Uani 1 1 d . .
H9 H 0.0110 0.4937 0.8432 0.022 Uiso 1 1 calc R U
C12 C 0.24008(16) 0.52212(8) 0.54344(17) 0.0114(4) Uani 1 1 d . .
C2 C 0.14990(17) 0.44015(8) 0.44374(18) 0.0132(4) Uani 1 1 d . .
C10 C 0.12203(17) 0.51523(9) 0.72679(18) 0.0136(4) Uani 1 1 d . .
H10 H 0.1521 0.5471 0.7689 0.016 Uiso 1 1 calc R U
C4 C 0.01545(19) 0.36288(9) 0.4135(2) 0.0194(4) Uani 1 1 d . .
H4 H -0.0165 0.3331 0.3652 0.023 Uiso 1 1 calc R U
C22 C 0.33489(18) 0.68761(9) 0.7614(2) 0.0182(4) Uani 1 1 d . .
H22 H 0.3228 0.7264 0.7579 0.022 Uiso 1 1 calc R U
C11 C 0.16036(16) 0.49856(8) 0.62010(18) 0.0116(4) Uani 1 1 d . .
C5 C -0.02274(18) 0.37335(9) 0.5230(2) 0.0187(4) Uani 1 1 d . .
H5 H -0.0793 0.3506 0.5476 0.022 Uiso 1 1 calc R U
C1 C 0.23141(16) 0.48567(8) 0.42922(17) 0.0116(4) Uani 1 1 d . .
C21 C 0.31351(17) 0.65604(9) 0.65477(19) 0.0157(4) Uani 1 1 d . .
H21 H 0.2892 0.6736 0.5802 0.019 Uiso 1 1 calc R U
C20 C 0.32887(16) 0.59783(9) 0.66068(18) 0.0121(4) Uani 1 1 d . .
C18 C 0.31812(18) 0.41438(9) 0.23539(19) 0.0160(4) Uani 1 1 d . .
H18 H 0.3330 0.3948 0.3090 0.019 Uiso 1 1 calc R U
C17 C 0.32208(19) 0.38667(9) 0.1253(2) 0.0186(4) Uani 1 1 d . .
H17 H 0.3395 0.3484 0.1260 0.022 Uiso 1 1 calc R U
C16 C 0.30058(19) 0.41497(10) 0.0141(2) 0.0180(4) Uani 1 1 d . .
C13 C 0.29172(17) 0.47156(9) 0.23470(18) 0.0130(4) Uani 1 1 d . .
C3 C 0.10206(18) 0.39600(9) 0.37191(19) 0.0158(4) Uani 1 1 d . .
H3 H 0.1263 0.3882 0.2973 0.019 Uiso 1 1 calc R U
C14 C 0.27488(19) 0.50139(9) 0.12482(19) 0.0172(4) Uani 1 1 d . .
H14 H 0.2612 0.5400 0.1244 0.021 Uiso 1 1 calc R U
C25 C 0.37099(18) 0.57190(9) 0.7709(2) 0.0170(4) Uani 1 1 d . .
H25 H 0.3841 0.5332 0.7740 0.020 Uiso 1 1 calc R U
C23 C 0.37427(18) 0.66235(10) 0.87381(19) 0.0185(4) Uani 1 1 d . .
C15 C 0.2788(2) 0.47267(10) 0.01603(19) 0.0199(4) Uani 1 1 d . .
H15 H 0.2667 0.4925 -0.0574 0.024 Uiso 1 1 calc R U
C28 C 0.30974(19) 0.29958(10) 0.6143(2) 0.0194(4) Uani 1 1 d . .
H28 H 0.3084 0.3406 0.6256 0.023 Uiso 1 1 calc R U
C24 C 0.39327(18) 0.60433(10) 0.87642(19) 0.0195(4) Uani 1 1 d . .
H24 H 0.4214 0.5870 0.9502 0.023 Uiso 1 1 calc R U
C8 C -0.01185(18) 0.43592(9) 0.7104(2) 0.0179(4) Uani 1 1 d . .
H8 H -0.0675 0.4155 0.7430 0.021 Uiso 1 1 calc R U
C26 C 0.4001(2) 0.69740(11) 0.9889(2) 0.0268(5) Uani 1 1 d . .
H26A H 0.4815 0.7009 1.0111 0.040 Uiso 1 1 calc R U
H26B H 0.3683 0.6794 1.0541 0.040 Uiso 1 1 calc R U
H26C H 0.3669 0.7342 0.9746 0.040 Uiso 1 1 calc R U
C27 C 0.0811(2) 0.67535(10) 0.0271(2) 0.0238(5) Uani 1 1 d . .
H27 H 0.1557 0.6702 0.0779 0.029 Uiso 1 1 calc R U
C19 C 0.3028(2) 0.38495(11) -0.1060(2) 0.0284(5) Uani 1 1 d . .
H19A H 0.2332 0.3926 -0.1600 0.043 Uiso 1 1 calc R U
H19B H 0.3098 0.3451 -0.0918 0.043 Uiso 1 1 calc R U
H19C H 0.3669 0.3980 -0.1425 0.043 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 '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
N2 Zn1 N1 81.07(7)
N2 Zn1 Cl1 118.73(5)
N1 Zn1 Cl1 112.07(5)
N2 Zn1 Cl2 107.81(5)
N1 Zn1 Cl2 111.19(5)
Cl1 Zn1 Cl2 119.60(2)
C1 N1 C13 123.30(17)
C1 N1 Zn1 111.98(13)
C13 N1 Zn1 124.68(13)
C12 N2 C20 121.59(17)
C12 N2 Zn1 111.50(13)
C20 N2 Zn1 126.92(13)
C7 C6 C5 116.6(2)
C7 C6 C8 116.69(19)
C5 C6 C8 126.7(2)
C6 C7 C2 123.10(19)
C6 C7 C11 122.59(19)
C2 C7 C11 114.23(18)
C8 C9 C10 122.6(2)
N2 C12 C11 134.72(19)
N2 C12 C1 118.23(18)
C11 C12 C1 106.98(16)
C3 C2 C7 118.57(19)
C3 C2 C1 135.4(2)
C7 C2 C1 105.83(17)
C11 C10 C9 118.59(19)
C5 C4 C3 122.0(2)
C21 C22 C23 121.3(2)
C10 C11 C7 119.21(18)
C10 C11 C12 134.64(19)
C7 C11 C12 105.91(17)
C4 C5 C6 120.6(2)
N1 C1 C2 136.00(19)
N1 C1 C12 116.81(17)
C2 C1 C12 106.99(17)
C22 C21 C20 119.3(2)
C25 C20 C21 120.46(19)
C25 C20 N2 119.96(18)
C21 C20 N2 119.50(18)
C17 C18 C13 119.5(2)
C18 C17 C16 121.4(2)
C17 C16 C15 118.1(2)
C17 C16 C19 121.7(2)
C15 C16 C19 120.2(2)
C18 C13 C14 120.17(19)
C18 C13 N1 122.38(18)
C14 C13 N1 117.36(18)
C2 C3 C4 119.1(2)
C15 C14 C13 119.1(2)
C24 C25 C20 119.4(2)
C24 C23 C22 118.26(19)
C24 C23 C26 120.9(2)
C22 C23 C26 120.8(2)
C14 C15 C16 121.6(2)
Cl7 C28 Cl8 110.09(12)
Cl7 C28 Cl6 110.54(13)
Cl8 C28 Cl6 110.08(12)
C25 C24 C23 121.3(2)
C9 C8 C6 120.3(2)
Cl4 C27 Cl5 111.18(13)
Cl4 C27 Cl3 109.95(14)
Cl5 C27 Cl3 110.36(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Zn1 N2 2.0805(17)
Zn1 N1 2.0858(17)
Zn1 Cl1 2.1961(6)
Zn1 Cl2 2.2292(5)
Cl7 C28 1.755(2)
Cl6 C28 1.761(2)
Cl8 C28 1.760(2)
Cl4 C27 1.753(2)
Cl3 C27 1.763(3)
Cl5 C27 1.756(3)
N1 C1 1.287(3)
N1 C13 1.422(3)
N2 C12 1.279(3)
N2 C20 1.431(2)
C6 C7 1.412(3)
C6 C5 1.416(3)
C6 C8 1.421(3)
C7 C2 1.414(3)
C7 C11 1.419(3)
C9 C8 1.375(3)
C9 C10 1.414(3)
C12 C11 1.466(3)
C12 C1 1.521(3)
C2 C3 1.383(3)
C2 C1 1.470(3)
C10 C11 1.381(3)
C4 C5 1.374(3)
C4 C3 1.418(3)
C22 C21 1.387(3)
C22 C23 1.396(3)
C21 C20 1.392(3)
C20 C25 1.390(3)
C18 C17 1.389(3)
C18 C13 1.391(3)
C17 C16 1.390(3)
C16 C15 1.392(3)
C16 C19 1.509(3)
C13 C14 1.394(3)
C14 C15 1.388(3)
C25 C24 1.389(3)
C23 C24 1.393(3)
C23 C26 1.512(3)
