#------------------------------------------------------------------------------
#$Date: 2015-10-09 11:09:46 +0300 (Fri, 09 Oct 2015) $
#$Revision: 161228 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/64/7036422.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_7036422
loop_
_publ_author_name
'Liu, Jian-Jun'
'Guan, Ying-Fang'
'Chen, Yong'
'Lin, Mei-Jin'
'Huang, Chang-Cang'
'Dai, Wen-Xin'
_publ_section_title
;
 The impact of lone pair-π interactions on photochromic properties in 1-D
 naphthalene diimide coordination networks.
;
_journal_issue                   39
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              17312
_journal_page_last               17317
_journal_paper_doi               10.1039/c5dt02970h
_journal_volume                  44
_journal_year                    2015
_chemical_formula_moiety         'C24 H12 Cl2 N4 O4 Zn'
_chemical_formula_sum            'C24 H12 Cl2 N4 O4 Zn'
_chemical_formula_weight         556.65
_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   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2015-07-16 deposited with the CCDC.
2015-09-07 downloaded from the CCDC.
;
_cell_angle_alpha                108.44(3)
_cell_angle_beta                 93.66(3)
_cell_angle_gamma                111.61(3)
_cell_formula_units_Z            2
_cell_length_a                   11.913(2)
_cell_length_b                   12.215(2)
_cell_length_c                   13.877(3)
_cell_measurement_reflns_used    4901
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4971
_cell_measurement_theta_min      3.0427
_cell_volume                     1743.4(8)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Saturn724 (2x2 bin mode)'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_laue_measured_fraction_full 0.979
_diffrn_reflns_laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14628
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.524
_diffrn_reflns_theta_min         3.041
_exptl_absorpt_coefficient_mu    0.884
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.060
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_platon_squeeze_details
;
SQUEEZE removed 2.5 disordered NMP  molecules per formula unit. 
This value calculated based upon volume/count_electrons analysis and TG-MS analysis.
;
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         7681
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0516
_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)+(0.0881P)²+1.1598P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1450
_refine_ls_wR_factor_ref         0.1525
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6540
_reflns_number_total             7681
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5dt02970h2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7036422--7036424.cif.
;
_cod_original_cell_volume        1743.4(7)
_cod_database_code               7036422
_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.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_adp
Zn1 Zn 0.83826(3) 0.64628(3) 0.19885(3) 0.03357(12) Uani 1 1 d . .
Cl1 Cl 0.87565(8) 0.82968(8) 0.32287(6) 0.0510(2) Uani 1 1 d . .
Cl2 Cl 0.87249(7) 0.63068(8) 0.03964(6) 0.04296(18) Uani 1 1 d . .
O1 O 0.33001(18) 0.2010(2) -0.07492(17) 0.0435(5) Uani 1 1 d . .
O2 O 0.2686(2) 0.2918(2) 0.25398(18) 0.0532(6) Uani 1 1 d . .
O3 O 1.36451(19) 0.6631(2) 0.32283(19) 0.0488(6) Uani 1 1 d . .
O4 O 1.11401(17) 0.3669(2) 0.43556(16) 0.0412(5) Uani 1 1 d . .
N1 N 0.6586(2) 0.5247(2) 0.1817(2) 0.0360(5) Uani 1 1 d . .
N2 N 0.29444(19) 0.2499(2) 0.08866(19) 0.0328(5) Uani 1 1 d . .
N3 N 0.9461(2) 0.5710(3) 0.2535(2) 0.0395(6) Uani 1 1 d . .
N4 N 1.2402(2) 0.5169(2) 0.38218(18) 0.0328(5) Uani 1 1 d . .
C1 C 0.5683(2) 0.5477(2) 0.1418(2) 0.0331(6) Uani 1 1 d . .
H1 H 0.5879 0.6245 0.1331 0.040 Uiso 1 1 calc R U
C2 C 0.4466(2) 0.4604(3) 0.1131(2) 0.0327(6) Uani 1 1 d . .
H2 H 0.3849 0.4785 0.0862 0.039 Uiso 1 1 calc R U
C3 C 0.4187(2) 0.3468(3) 0.1251(2) 0.0359(6) Uani 1 1 d . .
C4 C 0.5091(3) 0.3279(3) 0.1757(3) 0.0574(10) Uani 1 1 d . .
H4 H 0.4906 0.2548 0.1905 0.069 Uiso 1 1 calc R U
C5 C 0.6276(3) 0.4200(3) 0.2036(3) 0.0548(9) Uani 1 1 d . .
H5 H 0.6887 0.4087 0.2394 0.066 Uiso 1 1 calc R U
C6 C 0.2263(3) 0.2275(3) 0.1634(2) 0.0373(6) Uani 1 1 d . .
C7 C 0.1005(2) 0.1232(3) 0.1242(2) 0.0358(6) Uani 1 1 d . .
C8 C 0.0596(2) 0.0494(2) 0.0177(2) 0.0298(5) Uani 1 1 d . .
C9 C 0.1344(2) 0.0729(3) -0.0540(2) 0.0342(6) Uani 1 1 d . .
C10 C 0.2596(2) 0.1769(3) -0.0178(2) 0.0344(6) Uani 1 1 d . .
C11 C 0.0926(3) 0.0006(3) -0.1576(3) 0.0467(7) Uani 1 1 d . .
H11 H 0.1429 0.0171 -0.2044 0.056 Uiso 1 1 calc R U
C12 C 0.0262(3) 0.0986(3) 0.1936(3) 0.0472(7) Uani 1 1 d . .
H12 H 0.0544 0.1473 0.2640 0.057 Uiso 1 1 calc R U
C13 C 1.0039(3) 0.5100(3) 0.1924(2) 0.0392(6) Uani 1 1 d . .
H13 H 0.9786 0.4820 0.1208 0.047 Uiso 1 1 calc R U
C14 C 1.0988(3) 0.4873(3) 0.2310(2) 0.0395(6) Uani 1 1 d . .
H14 H 1.1379 0.4456 0.1868 0.047 Uiso 1 1 calc R U
C15 C 1.1343(2) 0.5278(3) 0.3370(2) 0.0360(6) Uani 1 1 d . .
C16 C 1.0708(3) 0.5827(4) 0.4006(2) 0.0477(8) Uani 1 1 d . .
H16 H 1.0901 0.6050 0.4721 0.057 Uiso 1 1 calc R U
C17 C 0.9784(3) 0.6038(4) 0.3562(3) 0.0498(8) Uani 1 1 d . .
H17 H 0.9363 0.6425 0.3993 0.060 Uiso 1 1 calc R U
C18 C 1.2188(2) 0.4316(3) 0.4335(2) 0.0347(6) Uani 1 1 d . .
C19 C 1.3292(2) 0.4257(3) 0.4833(2) 0.0319(5) Uani 1 1 d . .
C20 C 1.4478(2) 0.5030(3) 0.4764(2) 0.0299(5) Uani 1 1 d . .
C21 C 1.4649(2) 0.5867(3) 0.4217(2) 0.0327(6) Uani 1 1 d . .
C22 C 1.3560(3) 0.5934(3) 0.3707(2) 0.0354(6) Uani 1 1 d . .
C23 C 1.5811(3) 0.6610(3) 0.4161(2) 0.0367(6) Uani 1 1 d . .
H23 H 1.5912 0.7152 0.3799 0.044 Uiso 1 1 calc R U
C24 C 1.3148(2) 0.3441(3) 0.5352(2) 0.0368(6) Uani 1 1 d . .
H24 H 1.2362 0.2923 0.5382 0.044 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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
H H 0.0000 0.0000 '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
N1 Zn1 N3 106.11(10) . .
N1 Zn1 Cl1 108.77(9) . .
N3 Zn1 Cl1 106.40(9) . .
N1 Zn1 Cl2 106.97(9) . .
N3 Zn1 Cl2 104.89(8) . .
Cl1 Zn1 Cl2 122.59(4) . .
C5 N1 C1 118.2(2) . .
C5 N1 Zn1 123.01(19) . .
C1 N1 Zn1 118.73(18) . .
C6 N2 C10 125.9(2) . .
C6 N2 C3 117.1(2) . .
C10 N2 C3 116.5(2) . .
C17 N3 C13 117.8(2) . .
C17 N3 Zn1 118.8(2) . .
C13 N3 Zn1 122.25(19) . .
C18 N4 C22 125.9(2) . .
C18 N4 C15 117.4(2) . .
C22 N4 C15 116.8(2) . .
N1 C1 C2 121.9(2) . .
N1 C1 H1 119.0 . .
C2 C1 H1 119.0 . .
C3 C2 C1 118.7(2) . .
C3 C2 H2 120.6 . .
C1 C2 H2 120.6 . .
C2 C3 C4 119.4(3) . .
C2 C3 N2 120.2(2) . .
C4 C3 N2 120.4(2) . .
C5 C4 C3 118.2(3) . .
C5 C4 H4 120.9 . .
C3 C4 H4 120.9 . .
N1 C5 C4 122.8(3) . .
N1 C5 H5 118.6 . .
C4 C5 H5 118.6 . .
O2 C6 N2 120.3(3) . .
O2 C6 C7 123.5(3) . .
N2 C6 C7 116.1(3) . .
C12 C7 C8 120.7(3) . .
C12 C7 C6 119.3(3) . .
C8 C7 C6 120.0(3) . .
C9 C8 C7 121.4(2) . .
C9 C8 C8 119.5(3) . 2
C7 C8 C8 119.0(3) . 2
C11 C9 C8 120.6(3) . .
C11 C9 C10 119.5(3) . .
C8 C9 C10 120.0(3) . .
O1 C10 N2 120.1(2) . .
O1 C10 C9 123.6(3) . .
N2 C10 C9 116.3(2) . .
C9 C11 C12 120.4(3) . 2
C9 C11 H11 119.8 . .
C12 C11 H11 119.8 2 .
C7 C12 C11 119.8(3) . 2
C7 C12 H12 120.1 . .
C11 C12 H12 120.1 2 .
N3 C13 C14 122.8(3) . .
N3 C13 H13 118.6 . .
C14 C13 H13 118.6 . .
C15 C14 C13 118.1(3) . .
C15 C14 H14 121.0 . .
C13 C14 H14 121.0 . .
C16 C15 C14 119.9(3) . .
C16 C15 N4 119.5(3) . .
C14 C15 N4 120.6(2) . .
C17 C16 C15 118.4(3) . .
C17 C16 H16 120.8 . .
C15 C16 H16 120.8 . .
N3 C17 C16 122.8(3) . .
N3 C17 H17 118.6 . .
C16 C17 H17 118.6 . .
O4 C18 N4 120.1(2) . .
O4 C18 C19 123.4(3) . .
N4 C18 C19 116.5(2) . .
C24 C19 C20 120.6(2) . .
C24 C19 C18 119.5(2) . .
C20 C19 C18 119.9(2) . .
C20 C20 C19 119.6(3) 2_866 .
C20 C20 C21 118.7(3) 2_866 .
C19 C20 C21 121.6(2) . .
C23 C21 C20 120.6(2) . .
C23 C21 C22 120.0(2) . .
C20 C21 C22 119.4(2) . .
O3 C22 N4 120.8(2) . .
O3 C22 C21 122.6(3) . .
N4 C22 C21 116.6(2) . .
C21 C23 C24 120.4(3) . 2_866
C21 C23 H23 119.8 . .
C24 C23 H23 119.8 2_866 .
C19 C24 C23 120.0(3) . 2_866
C19 C24 H24 120.0 . .
C23 C24 H24 120.0 2_866 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 N1 2.052(2) .
Zn1 N3 2.064(2) .
Zn1 Cl1 2.2152(13) .
Zn1 Cl2 2.2338(10) .
O1 C10 1.212(3) .
O2 C6 1.206(4) .
O3 C22 1.215(3) .
O4 C18 1.215(3) .
N1 C5 1.333(4) .
N1 C1 1.337(3) .
N2 C6 1.391(4) .
N2 C10 1.402(4) .
N2 C3 1.443(3) .
N3 C17 1.340(4) .
N3 C13 1.342(4) .
N4 C18 1.399(3) .
N4 C22 1.405(4) .
N4 C15 1.442(3) .
C1 C2 1.385(4) .
C1 H1 0.9300 .
C2 C3 1.370(4) .
C2 H2 0.9300 .
C3 C4 1.377(4) .
C4 C5 1.376(4) .
C4 H4 0.9300 .
C5 H5 0.9300 .
C6 C7 1.488(4) .
C7 C12 1.377(4) .
C7 C8 1.406(4) .
C8 C9 1.403(4) .
C8 C8 1.411(5) 2
C9 C11 1.369(4) .
C9 C10 1.482(4) .
C11 C12 1.409(4) 2
C11 H11 0.9300 .
C12 C11 1.409(4) 2
C12 H12 0.9300 .
C13 C14 1.377(4) .
C13 H13 0.9300 .
C14 C15 1.375(4) .
C14 H14 0.9300 .
C15 C16 1.373(4) .
C16 C17 1.372(4) .
C16 H16 0.9300 .
C17 H17 0.9300 .
C18 C19 1.482(3) .
C19 C24 1.373(4) .
C19 C20 1.410(4) .
C20 C20 1.405(5) 2_866
C20 C21 1.421(4) .
C21 C23 1.371(4) .
C21 C22 1.480(3) .
C23 C24 1.405(4) 2_866
C23 H23 0.9300 .
C24 C23 1.405(4) 2_866
C24 H24 0.9300 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C5 N1 C1 C2 -6.9(5) . .
Zn1 N1 C1 C2 169.9(2) . .
N1 C1 C2 C3 -0.7(5) . .
C1 C2 C3 C4 7.2(5) . .
C1 C2 C3 N2 -175.2(3) . .
C6 N2 C3 C2 -107.4(3) . .
C10 N2 C3 C2 80.3(3) . .
C6 N2 C3 C4 70.1(4) . .
C10 N2 C3 C4 -102.2(4) . .
C2 C3 C4 C5 -6.1(6) . .
N2 C3 C4 C5 176.3(3) . .
C1 N1 C5 C4 8.1(6) . .
Zn1 N1 C5 C4 -168.5(3) . .
C3 C4 C5 N1 -1.6(7) . .
C10 N2 C6 O2 175.3(3) . .
C3 N2 C6 O2 3.8(4) . .
C10 N2 C6 C7 -5.8(4) . .
C3 N2 C6 C7 -177.3(2) . .
O2 C6 C7 C12 1.0(5) . .
N2 C6 C7 C12 -177.8(3) . .
O2 C6 C7 C8 -177.6(3) . .
N2 C6 C7 C8 3.6(4) . .
C12 C7 C8 C9 -179.7(3) . .
C6 C7 C8 C9 -1.1(4) . .
C12 C7 C8 C8 1.0(5) . 2
C6 C7 C8 C8 179.6(3) . 2
C7 C8 C9 C11 -179.5(3) . .
C8 C8 C9 C11 -0.2(5) 2 .
C7 C8 C9 C10 0.4(4) . .
C8 C8 C9 C10 179.7(3) 2 .
C6 N2 C10 O1 -175.4(3) . .
C3 N2 C10 O1 -3.9(4) . .
C6 N2 C10 C9 5.2(4) . .
C3 N2 C10 C9 176.7(2) . .
C11 C9 C10 O1 -1.7(4) . .
C8 C9 C10 O1 178.5(3) . .
C11 C9 C10 N2 177.7(3) . .
C8 C9 C10 N2 -2.2(4) . .
C8 C9 C11 C12 -0.1(5) . 2
C10 C9 C11 C12 -179.9(3) . 2
C8 C7 C12 C11 -0.8(5) . 2
C6 C7 C12 C11 -179.4(3) . 2
C17 N3 C13 C14 -4.0(5) . .
Zn1 N3 C13 C14 163.3(2) . .
N3 C13 C14 C15 0.8(5) . .
C13 C14 C15 C16 3.7(5) . .
C13 C14 C15 N4 -174.4(3) . .
C18 N4 C15 C16 69.5(4) . .
C22 N4 C15 C16 -110.4(3) . .
C18 N4 C15 C14 -112.4(3) . .
C22 N4 C15 C14 67.7(4) . .
C14 C15 C16 C17 -4.6(5) . .
N4 C15 C16 C17 173.5(3) . .
C13 N3 C17 C16 3.0(5) . .
Zn1 N3 C17 C16 -164.8(3) . .
C15 C16 C17 N3 1.3(6) . .
C22 N4 C18 O4 -177.4(3) . .
C15 N4 C18 O4 2.7(4) . .
C22 N4 C18 C19 2.4(4) . .
C15 N4 C18 C19 -177.5(2) . .
O4 C18 C19 C24 -0.3(4) . .
N4 C18 C19 C24 179.8(3) . .
O4 C18 C19 C20 179.3(3) . .
N4 C18 C19 C20 -0.6(4) . .
C24 C19 C20 C20 -0.4(5) . 2_866
C18 C19 C20 C20 -180.0(3) . 2_866
C24 C19 C20 C21 179.0(3) . .
C18 C19 C20 C21 -0.6(4) . .
C20 C20 C21 C23 -0.7(5) 2_866 .
C19 C20 C21 C23 179.9(3) . .
C20 C20 C21 C22 179.5(3) 2_866 .
C19 C20 C21 C22 0.1(4) . .
C18 N4 C22 O3 178.7(3) . .
C15 N4 C22 O3 -1.4(4) . .
C18 N4 C22 C21 -2.9(4) . .
C15 N4 C22 C21 177.0(2) . .
C23 C21 C22 O3 0.1(5) . .
C20 C21 C22 O3 180.0(3) . .
C23 C21 C22 N4 -178.3(3) . .
C20 C21 C22 N4 1.5(4) . .
C20 C21 C23 C24 -0.2(4) . 2_866
C22 C21 C23 C24 179.6(3) . 2_866
C20 C19 C24 C23 1.3(4) . 2_866
C18 C19 C24 C23 -179.1(3) . 2_866
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.131 0.000 0.437 822 133 ' '
