#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/61/4336192.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_4336192
loop_
_publ_author_name
'Arnaud Parrot'
'Guillaume Izzet'
'Lise-Marie Chamoreau'
'Anna Proust'
'Olivier Oms'
'Anne Dolbecq'
'Khadija Hakouk'
'Houda El Bekkachi'
'Philippe Deniard'
'Rémi Dessapt'
'Pierre Mialane'
_publ_contact_author
;
      Pr P. Mialane
      Institut Lavoisier, ILV, UMR CNRS 8180
      Université de Versailles Saint-Quentin-en-Yvelines
      45 Avenue des Etats Unis
      78035 Versailles cedex
      France
;
_publ_contact_author_email       mialane@chimie.uvsq.fr
_publ_contact_author_fax         '(33) 1 39 25 43 81'
_publ_contact_author_phone       '(33) 1 39 25 43 83'
_publ_section_title
;
 Photochromic Properties of Polyoxotungstates with Grafted Spiropyran
 Molecules
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              11156
_journal_page_last               11163
_journal_paper_doi               10.1021/ic401380a
_journal_volume                  52
_journal_year                    2013
_chemical_formula_moiety         '0.9(C25 H20 N2 O3), 0.1(C25 H21 Br1 N2 O3)'
_chemical_formula_sum            'C25 H20.1 Br0.1 N2 O3'
_chemical_formula_weight         404.52
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 108.7490(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1197(6)
_cell_length_b                   10.7416(5)
_cell_length_c                   16.1456(8)
_cell_measurement_reflns_used    8653
_cell_measurement_temperature    200(1)
_cell_measurement_theta_max      29.89
_cell_measurement_theta_min      2.60
_cell_volume                     1990.38(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      200(1)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            27827
_diffrn_reflns_theta_full        30.06
_diffrn_reflns_theta_max         30.06
_diffrn_reflns_theta_min         1.84
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.7127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       block
_exptl_crystal_F_000             846
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         5807
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0514
_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)+(0.0374P)²+1.2300P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1324
_reflns_number_gt                4431
_reflns_number_total             5807
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ic401380a_si_002.cif
_cod_data_source_block           ap55
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C25 H20.10 Br0.10 N2 O3'
_cod_database_code               4336192
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.5500(8) 0.2513(10) 0.6717(7) 0.087(3) Uani 0.10 1 d P A 2
O1 O 0.25423(10) 0.19146(10) 0.59805(7) 0.0302(2) Uani 1 1 d . . .
O2 O 0.33250(14) 0.42918(14) 0.27000(10) 0.0547(4) Uani 1 1 d . . .
O3 O 0.34008(12) 0.23437(14) 0.23902(9) 0.0466(3) Uani 1 1 d . . .
N1 N 0.36694(12) 0.03237(14) 0.68859(9) 0.0324(3) Uani 1 1 d . . .
N2 N 0.32563(13) 0.31804(16) 0.28625(10) 0.0377(3) Uani 1 1 d . B .
C1 C 0.25341(14) 0.06196(14) 0.62785(10) 0.0282(3) Uani 1 1 d . B .
C2 C 0.17266(13) 0.06289(15) 0.68723(10) 0.0276(3) Uani 1 1 d . . .
C3 C 0.26121(13) 0.09294(14) 0.77605(10) 0.0257(3) Uani 1 1 d . B .
C4 C 0.37135(14) 0.07122(15) 0.77220(10) 0.0285(3) Uani 1 1 d . B .
C5 C 0.07266(15) 0.15545(19) 0.65166(11) 0.0373(4) Uani 1 1 d . B .
H5A H 0.0148 0.1416 0.6796 0.056 Uiso 1 1 calc R . .
H5B H 0.0384 0.1440 0.5897 0.056 Uiso 1 1 calc R . .
H5C H 0.1021 0.2388 0.6634 0.056 Uiso 1 1 calc R . .
C6 C 0.12309(18) -0.06735(18) 0.69268(13) 0.0421(4) Uani 1 1 d . B .
H6A H 0.1850 -0.1274 0.7063 0.063 Uiso 1 1 calc R . .
H6B H 0.0663 -0.0879 0.6375 0.063 Uiso 1 1 calc R . .
H6C H 0.0870 -0.0682 0.7376 0.063 Uiso 1 1 calc R . .
C7A C 0.4715(2) 0.0368(3) 0.66139(16) 0.0429(5) Uani 0.90 1 d P B 1
H7A H 0.5303 -0.0175 0.6991 0.051 Uiso 0.90 1 calc PR B 1
H7B H 0.4520 0.0051 0.6022 0.051 Uiso 0.90 1 calc PR B 1
C8A C 0.51998(19) 0.1612(3) 0.66451(15) 0.0435(5) Uani 0.90 1 d P B 1
C9A C 0.5543(5) 0.2636(6) 0.6732(4) 0.0333(9) Uani 0.90 1 d P B 1
H9A H 0.5817 0.3451 0.6802 0.040 Uiso 0.90 1 calc PR B 1
C7B C 0.458(3) -0.029(3) 0.6751(16) 0.063(8) Uani 0.10 1 d P A 2
H7C H 0.4363 -0.1156 0.6618 0.076 Uiso 0.10 1 calc PR A 2
H7D H 0.5240 -0.0267 0.7282 0.076 Uiso 0.10 1 calc PR A 2
C8B C 0.493(2) 0.029(2) 0.5982(16) 0.059(6) Uani 0.10 1 d P A 2
H8 H 0.4804 -0.0226 0.5498 0.070 Uiso 0.10 1 calc PR A 2
C9B C 0.5339(17) 0.130(2) 0.5912(17) 0.057(6) Uani 0.10 1 d P A 2
H9B H 0.5578 0.1452 0.5428 0.069 Uiso 0.10 1 calc PR A 2
C10 C 0.24573(13) 0.12426(14) 0.85652(10) 0.0256(3) Uani 1 1 d . . .
C11 C 0.13597(14) 0.14610(17) 0.86820(11) 0.0335(4) Uani 1 1 d . B .
H11 H 0.0685 0.1408 0.8202 0.040 Uiso 1 1 calc R . .
C12 C 0.12737(16) 0.17471(18) 0.94834(12) 0.0391(4) Uani 1 1 d . . .
H12 H 0.0545 0.1894 0.9539 0.047 Uiso 1 1 calc R B .
C13 C 0.22761(17) 0.18217(16) 1.02263(11) 0.0365(4) Uani 1 1 d . B .
H13 H 0.2209 0.2009 1.0770 0.044 Uiso 1 1 calc R . .
C14 C 0.33428(15) 0.16185(15) 1.01435(10) 0.0330(4) Uani 1 1 d . . .
H14 H 0.4001 0.1666 1.0637 0.040 Uiso 1 1 calc R B .
C15 C 0.34755(14) 0.13359(14) 0.93222(10) 0.0282(3) Uani 1 1 d . B .
C16 C 0.45900(14) 0.11453(16) 0.92380(11) 0.0340(4) Uani 1 1 d . . .
H16 H 0.5248 0.1232 0.9728 0.041 Uiso 1 1 calc R B .
C17 C 0.47240(14) 0.08378(17) 0.84567(12) 0.0356(4) Uani 1 1 d . B .
H17 H 0.5461 0.0714 0.8409 0.043 Uiso 1 1 calc R . .
C18 C 0.22016(16) -0.02654(16) 0.55221(11) 0.0358(4) Uani 1 1 d . . .
H18 H 0.1958 -0.1062 0.5608 0.043 Uiso 1 1 calc R B .
C19 C 0.22395(16) 0.00360(16) 0.47360(11) 0.0355(4) Uani 1 1 d . B .
H19 H 0.2058 -0.0559 0.4294 0.043 Uiso 1 1 calc R . .
C20 C 0.25615(14) 0.12838(15) 0.45565(10) 0.0291(3) Uani 1 1 d . . .
C21 C 0.27470(14) 0.16203(16) 0.37809(10) 0.0308(3) Uani 1 1 d . B .
H21 H 0.2689 0.1031 0.3347 0.037 Uiso 1 1 calc R . .
C22 C 0.30192(14) 0.28446(16) 0.36619(10) 0.0305(3) Uani 1 1 d . . .
C23 C 0.30948(15) 0.37509(16) 0.42879(11) 0.0328(3) Uani 1 1 d . B .
H23 H 0.3253 0.4573 0.4184 0.039 Uiso 1 1 calc R . .
C24 C 0.29329(15) 0.34234(15) 0.50677(11) 0.0310(3) Uani 1 1 d . . .
H24 H 0.2987 0.4022 0.5495 0.037 Uiso 1 1 calc R B .
C25 C 0.26879(13) 0.21913(14) 0.52081(10) 0.0265(3) Uani 1 1 d . B .
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'
Br Br -0.2901 2.4595 '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
C25 O1 C1 121.82(12)
C7B N1 C4 121.2(11)
C7B N1 C1 129.8(11)
C4 N1 C1 108.80(13)
C4 N1 C7A 120.68(15)
C1 N1 C7A 120.97(15)
O3 N2 O2 123.02(16)
O3 N2 C22 118.56(15)
O2 N2 C22 118.41(16)
N1 C1 O1 108.93(13)
N1 C1 C18 111.21(14)
O1 C1 C18 111.19(13)
N1 C1 C2 103.34(12)
O1 C1 C2 105.29(12)
C18 C1 C2 116.34(14)
C3 C2 C5 116.67(13)
C3 C2 C6 108.01(13)
C5 C2 C6 109.65(14)
C3 C2 C1 100.76(12)
C5 C2 C1 110.36(13)
C6 C2 C1 111.10(13)
C4 C3 C10 119.98(14)
C4 C3 C2 108.75(13)
C10 C3 C2 130.90(14)
C3 C4 N1 110.97(14)
C3 C4 C17 122.56(15)
N1 C4 C17 126.44(15)
C8A C7A N1 113.39(18)
C9A C8A C7A 173.5(3)
N1 C7B C8B 112(2)
C9B C8B C7B 131(2)
C8B C9B Br1 122(2)
C3 C10 C11 124.62(14)
C3 C10 C15 117.94(14)
C11 C10 C15 117.44(14)
C12 C11 C10 121.48(15)
C11 C12 C13 120.79(17)
C14 C13 C12 119.62(16)
C13 C14 C15 121.55(15)
C16 C15 C14 121.26(14)
C16 C15 C10 119.63(14)
C14 C15 C10 119.11(15)
C17 C16 C15 121.68(15)
C16 C17 C4 118.15(15)
C19 C18 C1 122.90(15)
C18 C19 C20 120.75(15)
C21 C20 C25 118.93(15)
C21 C20 C19 123.51(15)
C25 C20 C19 117.56(14)
C22 C21 C20 119.15(15)
C21 C22 C23 121.96(15)
C21 C22 N2 118.85(15)
C23 C22 N2 119.18(15)
C24 C23 C22 119.40(15)
C23 C24 C25 119.44(15)
O1 C25 C24 117.32(14)
O1 C25 C20 121.62(14)
C24 C25 C20 121.02(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C9B 1.81(3)
O1 C25 1.3476(19)
O1 C1 1.4730(19)
O2 N2 1.231(2)
O3 N2 1.227(2)
N1 C7B 1.36(3)
N1 C4 1.397(2)
N1 C1 1.445(2)
N1 C7A 1.469(3)
N2 C22 1.455(2)
C1 C18 1.497(2)
C1 C2 1.575(2)
C2 C3 1.524(2)
C2 C5 1.530(2)
C2 C6 1.536(2)
C3 C4 1.376(2)
C3 C10 1.412(2)
C4 C17 1.411(2)
C7A C8A 1.454(4)
C8A C9A 1.168(7)
C7B C8B 1.57(3)
C8B C9B 1.21(3)
C10 C11 1.422(2)
C10 C15 1.434(2)
C11 C12 1.366(2)
C12 C13 1.409(3)
C13 C14 1.359(3)
C14 C15 1.419(2)
C15 C16 1.415(2)
C16 C17 1.363(3)
C18 C19 1.325(2)
C19 C20 1.451(2)
C20 C21 1.389(2)
C20 C25 1.406(2)
C21 C22 1.384(2)
C22 C23 1.385(2)
C23 C24 1.381(2)
C24 C25 1.391(2)
