#------------------------------------------------------------------------------
#$Date: 2017-02-04 15:34:25 +0200 (Sat, 04 Feb 2017) $
#$Revision: 191511 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/43/1544314.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_1544314
loop_
_publ_author_name
'Wu, Nathan Man-Wai'
'Wong, Hok-Lai'
'Yam, Vivian Wing-Wah'
_publ_section_title
;
 Photochromic benzo[b]phosphole oxide with excellent thermal
 irreversibility and fatigue resistance in the thin film solid state via
 direct attachment of dithienyl units to the weakly aromatic heterocycle
;
_journal_issue                   2
_journal_name_full               'Chem. Sci.'
_journal_page_first              1309
_journal_paper_doi               10.1039/C6SC02928K
_journal_volume                  8
_journal_year                    2017
_chemical_formula_sum            'C26 H23 O P S2'
_chemical_formula_weight         446.53
_chemical_name_systematic        BzPPh(O)-DTE
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-03-24 deposited with the CCDC.
2016-09-30 downloaded from the CCDC.
;
_cell_angle_alpha                83.4270(10)
_cell_angle_beta                 77.3210(10)
_cell_angle_gamma                83.7100(10)
_cell_formula_units_Z            2
_cell_length_a                   8.4616(4)
_cell_length_b                   11.5086(5)
_cell_length_c                   12.4957(6)
_cell_measurement_reflns_used    82
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     1174.89(9)
_computing_cell_refinement       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_collection       'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_data_reduction        'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_computing_molecular_graphics    'SIEMENS SHELXTL'
_computing_publication_material  'SIEMENS SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'BRUKER KAPPA APEXII DUO DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_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  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16694
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.310
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6503
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4226
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0443
_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)+(0.0596P)²+0.6731P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1232
_reflns_number_gt                3491
_reflns_number_total             4226
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6sc02928k2.cif
_cod_data_source_block           N14
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1544314.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1544314
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 1.03019(9) -0.06748(6) 0.13833(6) 0.0656(2) Uani 1 1 d .
S2 S 0.65893(11) 0.32086(7) -0.04446(6) 0.0740(3) Uani 1 1 d .
P1 P 0.56153(6) 0.35513(5) 0.38144(5) 0.03614(16) Uani 1 1 d .
O1 O 0.61929(18) 0.47390(13) 0.37025(14) 0.0468(4) Uani 1 1 d .
C1 C 0.8652(6) -0.2678(3) 0.2277(4) 0.1172(16) Uani 1 1 d .
H1B H 0.7730 -0.2914 0.2824 0.176 Uiso 1 1 calc R
H1C H 0.9625 -0.3102 0.2442 0.176 Uiso 1 1 calc R
H1D H 0.8531 -0.2843 0.1565 0.176 Uiso 1 1 calc R
C2 C 0.8765(4) -0.1378(2) 0.2274(2) 0.0668(8) Uani 1 1 d .
C3 C 0.7765(3) -0.0598(2) 0.2890(2) 0.0567(7) Uani 1 1 d .
H3A H 0.6867 -0.0810 0.3426 0.068 Uiso 1 1 calc R
C4 C 0.8204(3) 0.05846(19) 0.26485(19) 0.0433(5) Uani 1 1 d .
C5 C 0.9569(3) 0.0681(2) 0.1837(2) 0.0486(6) Uani 1 1 d .
C6 C 1.0444(3) 0.1744(2) 0.1344(3) 0.0675(8) Uani 1 1 d .
H6A H 0.9881 0.2424 0.1682 0.101 Uiso 1 1 calc R
H6B H 1.0478 0.1853 0.0566 0.101 Uiso 1 1 calc R
H6C H 1.1533 0.1638 0.1468 0.101 Uiso 1 1 calc R
C7 C 0.5697(4) 0.1193(3) 0.0947(3) 0.0735(8) Uani 1 1 d .
H7A H 0.5635 0.0853 0.1692 0.110 Uiso 1 1 calc R
H7B H 0.6423 0.0697 0.0454 0.110 Uiso 1 1 calc R
H7C H 0.4635 0.1266 0.0778 0.110 Uiso 1 1 calc R
C8 C 0.6314(3) 0.2377(2) 0.0820(2) 0.0535(6) Uani 1 1 d .
C9 C 0.6691(3) 0.29870(19) 0.15934(19) 0.0449(5) Uani 1 1 d .
C10 C 0.7172(3) 0.4135(2) 0.1146(2) 0.0556(6) Uani 1 1 d .
H10A H 0.7448 0.4665 0.1568 0.067 Uiso 1 1 calc R
C11 C 0.7190(4) 0.4376(2) 0.0061(2) 0.0674(8) Uani 1 1 d .
C12 C 0.7673(5) 0.5477(3) -0.0663(3) 0.1027(13) Uani 1 1 d .
H12A H 0.7963 0.6025 -0.0229 0.154 Uiso 1 1 calc R
H12B H 0.6776 0.5824 -0.0981 0.154 Uiso 1 1 calc R
H12C H 0.8587 0.5284 -0.1240 0.154 Uiso 1 1 calc R
C13 C 0.7263(2) 0.15727(18) 0.32326(18) 0.0383(5) Uani 1 1 d .
C14 C 0.6630(2) 0.25910(18) 0.27641(18) 0.0387(5) Uani 1 1 d .
C15 C 0.6989(2) 0.15138(18) 0.44586(19) 0.0390(5) Uani 1 1 d .
C16 C 0.7606(3) 0.0626(2) 0.5148(2) 0.0504(6) Uani 1 1 d .
H16A H 0.8205 -0.0036 0.4860 0.061 Uiso 1 1 calc R
C17 C 0.7320(4) 0.0739(2) 0.6270(2) 0.0620(7) Uani 1 1 d .
H17A H 0.7735 0.0150 0.6732 0.074 Uiso 1 1 calc R
C18 C 0.6426(4) 0.1717(2) 0.6708(2) 0.0639(7) Uani 1 1 d .
H18A H 0.6245 0.1777 0.7462 0.077 Uiso 1 1 calc R
C19 C 0.5794(3) 0.2611(2) 0.6035(2) 0.0505(6) Uani 1 1 d .
H19A H 0.5181 0.3264 0.6331 0.061 Uiso 1 1 calc R
C20 C 0.6100(2) 0.25081(18) 0.49116(19) 0.0393(5) Uani 1 1 d .
C21 C 0.3472(2) 0.35744(19) 0.38623(18) 0.0393(5) Uani 1 1 d .
C22 C 0.2593(3) 0.4603(3) 0.3661(3) 0.0754(9) Uani 1 1 d .
H22A H 0.3101 0.5297 0.3493 0.090 Uiso 1 1 calc R
C23 C 0.0922(4) 0.4622(3) 0.3707(3) 0.0861(11) Uani 1 1 d .
H23A H 0.0324 0.5333 0.3581 0.103 Uiso 1 1 calc R
C24 C 0.0185(3) 0.3641(3) 0.3926(3) 0.0803(10) Uani 1 1 d .
H24A H -0.0926 0.3662 0.3957 0.096 Uiso 1 1 calc R
C25 C 0.1051(4) 0.2611(4) 0.4102(5) 0.130(2) Uani 1 1 d .
H25A H 0.0538 0.1919 0.4243 0.156 Uiso 1 1 calc R
C26 C 0.2689(4) 0.2575(3) 0.4076(4) 0.1013(14) Uani 1 1 d .
H26A H 0.3270 0.1858 0.4205 0.122 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
C2 S1 C5 93.05(12)
C11 S2 C8 93.37(13)
O1 P1 C21 113.36(10)
O1 P1 C20 118.27(10)
C21 P1 C20 107.94(10)
O1 P1 C14 116.24(10)
C21 P1 C14 106.33(10)
C20 P1 C14 92.37(10)
C3 C2 C1 128.9(3)
C3 C2 S1 110.0(2)
C1 C2 S1 121.1(2)
C2 C3 C4 114.2(2)
C5 C4 C3 112.3(2)
C5 C4 C13 125.0(2)
C3 C4 C13 122.7(2)
C4 C5 C6 129.7(2)
C4 C5 S1 110.41(18)
C6 C5 S1 119.88(18)
C9 C8 C7 129.4(2)
C9 C8 S2 110.01(19)
C7 C8 S2 120.5(2)
C8 C9 C10 112.2(2)
C8 C9 C14 127.1(2)
C10 C9 C14 120.7(2)
C11 C10 C9 114.3(3)
C10 C11 C12 127.8(3)
C10 C11 S2 110.1(2)
C12 C11 S2 122.1(3)
C14 C13 C4 126.6(2)
C14 C13 C15 113.78(19)
C4 C13 C15 119.57(18)
C13 C14 C9 129.8(2)
C13 C14 P1 110.60(17)
C9 C14 P1 119.59(15)
C16 C15 C20 119.3(2)
C16 C15 C13 126.5(2)
C20 C15 C13 114.10(18)
C17 C16 C15 119.4(2)
C18 C17 C16 120.8(2)
C17 C18 C19 120.8(2)
C20 C19 C18 118.5(2)
C19 C20 C15 121.3(2)
C19 C20 P1 129.45(17)
C15 C20 P1 109.14(16)
C22 C21 C26 118.0(2)
C22 C21 P1 120.15(19)
C26 C21 P1 121.83(19)
C21 C22 C23 120.2(3)
C24 C23 C22 120.7(3)
C23 C24 C25 119.7(3)
C24 C25 C26 120.5(3)
C21 C26 C25 120.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C2 1.724(3)
S1 C5 1.725(2)
S2 C11 1.717(3)
S2 C8 1.735(3)
P1 O1 1.4830(15)
P1 C21 1.799(2)
P1 C20 1.803(2)
P1 C14 1.819(2)
C1 C2 1.509(4)
C2 C3 1.349(4)
C3 C4 1.431(3)
C4 C5 1.365(3)
C4 C13 1.482(3)
C5 C6 1.501(4)
C7 C8 1.491(4)
C8 C9 1.367(4)
C9 C10 1.440(3)
C9 C14 1.473(3)
C10 C11 1.349(4)
C11 C12 1.511(4)
C13 C14 1.359(3)
C13 C15 1.493(3)
C15 C16 1.392(3)
C15 C20 1.403(3)
C16 C17 1.387(4)
C17 C18 1.383(4)
C18 C19 1.389(4)
C19 C20 1.387(3)
C21 C22 1.356(3)
C21 C26 1.361(4)
C22 C23 1.400(4)
C23 C24 1.322(5)
C24 C25 1.345(5)
C25 C26 1.375(4)
