#------------------------------------------------------------------------------
#$Date: 2016-03-25 16:23:51 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179967 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/61/7026158.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_7026158
loop_
_publ_author_name
'Natali, Manuel'
'Aakeröy, Christer'
'Desper, John'
'Giordani, Silvia'
_publ_section_title
;
 The role of metal ions and counterions in the switching behavior of a
 carboxylic acid functionalized spiropyran.
;
_journal_issue                   35
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              8269
_journal_page_last               8277
_journal_paper_doi               10.1039/c0dt00242a
_journal_volume                  39
_journal_year                    2010
_chemical_formula_moiety
;
(C23 H23 N2 O6) Zn Cl
;
_chemical_formula_sum            'C23 H23 Cl N2 O6 Zn'
_chemical_formula_weight         524.25
_chemical_name_common
'EH-02-77-01 methoxy nitro propiony spiropyran Zn(ClO4)2'
_chemical_name_systematic
;
EH-02-77-01 methoxy nitro propiony spiropyran Zn(ClO4)2
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.774(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.000(10)
_cell_length_b                   7.729(9)
_cell_length_c                   37.55(4)
_cell_measurement_reflns_used    4330
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      24.34
_cell_measurement_theta_min      8.01
_cell_volume                     2603(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.3846
_diffrn_reflns_av_sigmaI/netI    0.2150
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            61286
_diffrn_reflns_theta_full        28.92
_diffrn_reflns_theta_max         28.92
_diffrn_reflns_theta_min         7.77
_exptl_absorpt_coefficient_mu    1.084
_exptl_absorpt_correction_T_max  0.9378
_exptl_absorpt_correction_T_min  0.8457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         2.306
_refine_diff_density_min         -1.021
_refine_diff_density_rms         0.174
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.972
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         6509
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.971
_refine_ls_R_factor_all          0.3601
_refine_ls_R_factor_gt           0.2237
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4372
_refine_ls_wR_factor_ref         0.4679
_reflns_number_gt                2734
_reflns_number_total             6509
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0dt00242a.txt
_cod_data_source_block           eh0902m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7026158
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Zn1 Zn 0.5885(3) 0.2584(2) 0.30101(3) 0.0664(8) Uani 1 1 d .
Cl1 Cl 0.8329(6) 0.3397(5) 0.31313(10) 0.0863(17) Uani 1 1 d .
N11 N 0.2559(17) 0.7408(19) 0.3813(3) 0.078(4) Uani 1 1 d .
C12 C 0.287(3) 0.605(2) 0.4066(4) 0.100(8) Uani 1 1 d D
C13 C 0.2044(15) 0.6514(14) 0.4403(3) 0.075(5) Uani 1 1 d D
C14 C 0.1211(14) 0.8153(13) 0.4301(2) 0.065(5) Uani 1 1 d GD
C15 C 0.0267(13) 0.9184(14) 0.4485(2) 0.086(6) Uani 1 1 d G
H15 H 0.0041 0.8869 0.4719 0.103 Uiso 1 1 calc R
C16 C -0.0347(12) 1.0674(13) 0.4326(3) 0.104(8) Uani 1 1 d G
H16 H -0.0993 1.1378 0.4452 0.124 Uiso 1 1 calc R
C17 C -0.0017(15) 1.1133(13) 0.3984(3) 0.091(7) Uani 1 1 d G
H17 H -0.0437 1.2152 0.3876 0.109 Uiso 1 1 calc R
C18 C 0.0927(17) 1.0103(16) 0.3800(2) 0.103(8) Uani 1 1 d G
H18 H 0.1153 1.0417 0.3566 0.124 Uiso 1 1 calc R
C19 C 0.1542(15) 0.8612(15) 0.3959(2) 0.089(7) Uani 1 1 d G
C20 C 0.3164(19) 0.668(3) 0.4736(3) 0.102(7) Uani 1 1 d D
H20A H 0.3696 0.5587 0.4778 0.152 Uiso 1 1 calc R
H20B H 0.2627 0.6970 0.4945 0.152 Uiso 1 1 calc R
H20C H 0.3881 0.7604 0.4696 0.152 Uiso 1 1 calc R
C21 C 0.0994(16) 0.502(2) 0.4487(5) 0.084(6) Uani 1 1 d D
H21A H 0.0266 0.4829 0.4282 0.127 Uiso 1 1 calc R
H21B H 0.0470 0.5317 0.4698 0.127 Uiso 1 1 calc R
H21C H 0.1578 0.3963 0.4536 0.127 Uiso 1 1 calc R
C22 C 0.299(2) 0.765(2) 0.3439(3) 0.101(7) Uani 1 1 d DU
H22A H 0.4021 0.7207 0.3427 0.121 Uiso 1 1 calc R
H22B H 0.3005 0.8900 0.3386 0.121 Uiso 1 1 calc R
C23 C 0.1979(18) 0.675(3) 0.3145(3) 0.082(5) Uani 1 1 d DU
H23A H 0.0976 0.7279 0.3127 0.098 Uiso 1 1 calc R
H23B H 0.1874 0.5503 0.3202 0.098 Uiso 1 1 calc R
C24 C 0.270(2) 0.695(3) 0.2787(4) 0.103(6) Uani 1 1 d DU
H24A H 0.1910 0.6752 0.2593 0.124 Uiso 1 1 calc R
H24B H 0.3009 0.8178 0.2770 0.124 Uiso 1 1 calc R
C25 C 0.4051(16) 0.5832(18) 0.2706(3) 0.057(4) Uani 1 1 d DU
O25 O 0.4503(15) 0.4637(13) 0.2945(2) 0.080(4) Uani 1 1 d .
O26 O 0.4630(14) 0.5966(12) 0.2401(2) 0.070(3) Uani 1 1 d .
C27 C 0.377(2) 0.4514(17) 0.3963(3) 0.085(6) Uani 1 1 d D
H27 H 0.4169 0.4480 0.3737 0.103 Uiso 1 1 calc R
C28 C 0.4047(13) 0.2994(12) 0.4227(3) 0.039(3) Uiso 1 1 d D
H28 H 0.3633 0.2959 0.4451 0.047 Uiso 1 1 calc R
C31 C 0.5456(17) 0.1210(15) 0.3753(3) 0.044(3) Uani 1 1 d .
C32 C 0.6294(17) -0.0397(18) 0.3686(3) 0.051(4) Uani 1 1 d .
C33 C 0.6748(17) -0.1497(19) 0.3983(3) 0.064(4) Uani 1 1 d .
H33 H 0.7318 -0.2509 0.3949 0.076 Uiso 1 1 calc R
C34 C 0.6331(16) -0.105(2) 0.4337(4) 0.070(5) Uani 1 1 d .
C35 C 0.5494(19) 0.041(2) 0.4393(4) 0.066(5) Uani 1 1 d .
H35 H 0.5227 0.0659 0.4627 0.080 Uiso 1 1 calc R
C36 C 0.5015(17) 0.1578(16) 0.4103(3) 0.058(4) Uani 1 1 d D
O31 O 0.4925(13) 0.2135(11) 0.3474(2) 0.063(3) Uani 1 1 d .
O32 O 0.6584(12) -0.0652(11) 0.3336(2) 0.056(3) Uani 1 1 d .
N34 N 0.685(2) -0.221(2) 0.4634(4) 0.097(6) Uani 1 1 d .
O34 O 0.7389(17) -0.375(2) 0.4553(3) 0.109(5) Uani 1 1 d .
O35 O 0.6725(19) -0.178(2) 0.4943(3) 0.127(7) Uani 1 1 d .
C37 C 0.749(2) -0.2132(17) 0.3242(4) 0.067(5) Uani 1 1 d .
H37A H 0.7543 -0.2162 0.2983 0.101 Uiso 1 1 calc R
H37B H 0.7026 -0.3203 0.3320 0.101 Uiso 1 1 calc R
H37C H 0.8491 -0.2024 0.3362 0.101 Uiso 1 1 calc R
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'
Cl Cl 0.1484 0.1585 '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
O26 Zn1 O25 107.2(4) 2_645 .
O26 Zn1 O31 117.6(4) 2_645 .
O25 Zn1 O31 86.4(4) . .
O26 Zn1 Cl1 118.6(4) 2_645 .
O25 Zn1 Cl1 112.3(4) . .
O31 Zn1 Cl1 110.2(3) . .
C12 N11 C19 108.6(10) . .
C12 N11 C22 131.3(12) . .
C19 N11 C22 119.9(11) . .
N11 C12 C27 119.4(11) . .
N11 C12 C13 106.7(9) . .
C27 C12 C13 133.8(11) . .
C14 C13 C21 112.4(12) . .
C14 C13 C20 114.4(11) . .
C21 C13 C20 105.6(13) . .
C14 C13 C12 104.3(9) . .
C21 C13 C12 109.5(13) . .
C20 C13 C12 110.6(12) . .
C15 C14 C19 120.0 . .
C15 C14 C13 131.9(8) . .
C19 C14 C13 108.1(8) . .
C16 C15 C14 120.0 . .
C16 C15 H15 120.0 . .
C14 C15 H15 120.0 . .
C15 C16 C17 120.0 . .
C15 C16 H16 120.0 . .
C17 C16 H16 120.0 . .
C18 C17 C16 120.0 . .
C18 C17 H17 120.0 . .
C16 C17 H17 120.0 . .
C17 C18 C19 120.0 . .
C17 C18 H18 120.0 . .
C19 C18 H18 120.0 . .
C18 C19 C14 120.0 . .
C18 C19 N11 127.8(8) . .
C14 C19 N11 112.2(7) . .
C13 C20 H20A 109.5 . .
C13 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C13 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C13 C21 H21A 109.5 . .
C13 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C13 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
N11 C22 C23 115.6(12) . .
N11 C22 H22A 108.4 . .
C23 C22 H22A 108.4 . .
N11 C22 H22B 108.4 . .
C23 C22 H22B 108.4 . .
H22A C22 H22B 107.4 . .
C22 C23 C24 108.0(14) . .
C22 C23 H23A 110.1 . .
C24 C23 H23A 110.1 . .
C22 C23 H23B 110.1 . .
C24 C23 H23B 110.1 . .
H23A C23 H23B 108.4 . .
C25 C24 C23 120.6(13) . .
C25 C24 H24A 107.2 . .
C23 C24 H24A 107.2 . .
C25 C24 H24B 107.2 . .
C23 C24 H24B 107.2 . .
H24A C24 H24B 106.8 . .
O26 C25 O25 121.9(13) . .
O26 C25 C24 120.7(11) . .
O25 C25 C24 117.2(12) . .
C25 O25 Zn1 141.2(9) . .
C25 O26 Zn1 129.9(10) . 2_655
C12 C27 C28 119.8(10) . .
C12 C27 H27 120.1 . .
C28 C27 H27 120.1 . .
C36 C28 C27 115.1(9) . .
C36 C28 H28 122.5 . .
C27 C28 H28 122.5 . .
O31 C31 C36 120.6(10) . .
O31 C31 C32 118.1(9) . .
C36 C31 C32 120.4(9) . .
O32 C32 C33 126.4(12) . .
O32 C32 C31 114.9(10) . .
C33 C32 C31 118.6(11) . .
C32 C33 C34 119.5(13) . .
C32 C33 H33 120.2 . .
C34 C33 H33 120.2 . .
C35 C34 C33 121.1(12) . .
C35 C34 N34 121.7(13) . .
C33 C34 N34 117.1(13) . .
C34 C35 C36 121.7(12) . .
C34 C35 H35 119.2 . .
C36 C35 H35 119.2 . .
C31 C36 C35 118.5(10) . .
C31 C36 C28 130.1(10) . .
C35 C36 C28 111.4(10) . .
C31 O31 Zn1 128.2(9) . .
C32 O32 C37 119.7(10) . .
O35 N34 O34 121.9(12) . .
O35 N34 C34 119.9(13) . .
O34 N34 C34 118.1(13) . .
O32 C37 H37A 109.5 . .
O32 C37 H37B 109.5 . .
H37A C37 H37B 109.5 . .
O32 C37 H37C 109.5 . .
H37A C37 H37C 109.5 . .
H37B C37 H37C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O26 2.012(9) 2_645
Zn1 O25 2.019(11) .
Zn1 O31 2.037(9) .
Zn1 Cl1 2.296(7) .
N11 C12 1.430(18) .
N11 C19 1.445(15) .
N11 C22 1.500(16) .
C12 C27 1.502(5) .
C12 C13 1.57(2) .
C13 C14 1.505(5) .
C13 C21 1.541(5) .
C13 C20 1.544(5) .
C14 C15 1.3900 .
C14 C19 1.3900 .
C15 C16 1.3900 .
C15 H15 0.9500 .
C16 C17 1.3900 .
C16 H16 0.9500 .
C17 C18 1.3900 .
C17 H17 0.9500 .
C18 C19 1.3900 .
C18 H18 0.9500 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 C23 1.538(5) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
C23 C24 1.548(5) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C24 C25 1.544(5) .
C24 H24A 0.9900 .
C24 H24B 0.9900 .
C25 O26 1.298(15) .
C25 O25 1.328(16) .
O26 Zn1 2.012(9) 2_655
C27 C28 1.543(5) .
C27 H27 0.9500 .
C28 C36 1.497(5) .
C28 H28 0.9500 .
C31 O31 1.327(13) .
C31 C36 1.431(15) .
C31 C32 1.485(18) .
C32 O32 1.376(14) .
C32 C33 1.435(18) .
C33 C34 1.453(19) .
C33 H33 0.9500 .
C34 C35 1.39(2) .
C34 N34 1.476(18) .
C35 C36 1.453(17) .
C35 H35 0.9500 .
O32 C37 1.462(17) .
N34 O35 1.223(17) .
N34 O34 1.324(18) .
C37 H37A 0.9800 .
C37 H37B 0.9800 .
C37 H37C 0.9800 .
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
C19 N11 C12 C27 173.2(19) . .
C22 N11 C12 C27 -1(3) . .
C19 N11 C12 C13 -3(2) . .
C22 N11 C12 C13 -177.4(16) . .
N11 C12 C13 C14 3(2) . .
C27 C12 C13 C14 -173(2) . .
N11 C12 C13 C21 123.7(15) . .
C27 C12 C13 C21 -52(3) . .
N11 C12 C13 C20 -120.4(16) . .
C27 C12 C13 C20 64(3) . .
C21 C13 C14 C15 60.6(15) . .
C20 C13 C14 C15 -59.8(18) . .
C12 C13 C14 C15 179.2(13) . .
C21 C13 C14 C19 -120.3(12) . .
C20 C13 C14 C19 119.2(12) . .
C12 C13 C14 C19 -1.7(15) . .
C19 C14 C15 C16 0.0 . .
C13 C14 C15 C16 179.0(15) . .
C14 C15 C16 C17 0.0 . .
C15 C16 C17 C18 0.0 . .
C16 C17 C18 C19 0.0 . .
C17 C18 C19 C14 0.0 . .
C17 C18 C19 N11 -178.8(15) . .
C15 C14 C19 C18 0.0 . .
C13 C14 C19 C18 -179.2(12) . .
C15 C14 C19 N11 178.9(13) . .
C13 C14 C19 N11 -0.2(13) . .
C12 N11 C19 C18 -178.8(13) . .
C22 N11 C19 C18 -4(2) . .
C12 N11 C19 C14 2.3(18) . .
C22 N11 C19 C14 177.2(12) . .
C12 N11 C22 C23 84(3) . .
C19 N11 C22 C23 -89.4(19) . .
N11 C22 C23 C24 -173.4(13) . .
C22 C23 C24 C25 77(2) . .
C23 C24 C25 O26 177.8(16) . .
C23 C24 C25 O25 3(3) . .
O26 C25 O25 Zn1 -5(2) . .
C24 C25 O25 Zn1 169.5(15) . .
O26 Zn1 O25 C25 -53.6(17) 2_645 .
O31 Zn1 O25 C25 -171.4(16) . .
Cl1 Zn1 O25 C25 78.3(16) . .
O25 C25 O26 Zn1 177.8(10) . 2_655
C24 C25 O26 Zn1 4(2) . 2_655
N11 C12 C27 C28 -176.8(17) . .
C13 C12 C27 C28 -1(4) . .
C12 C27 C28 C36 -177.3(17) . .
O31 C31 C32 O32 7.4(19) . .
C36 C31 C32 O32 176.6(14) . .
O31 C31 C32 C33 -174.0(13) . .
C36 C31 C32 C33 -5(2) . .
O32 C32 C33 C34 -179.1(14) . .
C31 C32 C33 C34 2(2) . .
C32 C33 C34 C35 0(2) . .
C32 C33 C34 N34 -178.8(15) . .
C33 C34 C35 C36 -1(2) . .
N34 C34 C35 C36 178.3(16) . .
O31 C31 C36 C35 173.2(14) . .
C32 C31 C36 C35 4(2) . .
O31 C31 C36 C28 -4(2) . .
C32 C31 C36 C28 -173.1(15) . .
C34 C35 C36 C31 -1(2) . .
C34 C35 C36 C28 176.3(15) . .
C27 C28 C36 C31 -16(2) . .
C27 C28 C36 C35 167.0(14) . .
C36 C31 O31 Zn1 153.4(11) . .
C32 C31 O31 Zn1 -37.3(17) . .
O26 Zn1 O31 C31 92.6(11) 2_645 .
O25 Zn1 O31 C31 -159.9(11) . .
Cl1 Zn1 O31 C31 -47.5(11) . .
C33 C32 O32 C37 -2(2) . .
C31 C32 O32 C37 176.0(13) . .
C35 C34 N34 O35 -10(3) . .
C33 C34 N34 O35 169.4(17) . .
C35 C34 N34 O34 167.1(17) . .
C33 C34 N34 O34 -14(2) . .
