#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:11:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178424 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/45/4024598.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_4024598
loop_
_publ_author_name
'Laura Rivado-Casas'
'Diego Sampedro'
'Pedro J. Campos'
'Stefania Fusi'
'Vinicio Zanirato'
'Massimo Olivucci'
_publ_section_title
;
Fluorenylidene-Pyrroline Biomimetic Light-Driven Molecular Switches
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4666
_journal_page_last               4674
_journal_paper_doi               10.1021/jo802792j
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C31 H30 F3 N1 O6 S1'
_chemical_formula_sum            'C31 H30 F3 N O6 S'
_chemical_formula_weight         601.62
_chemical_name_systematic
;
 ?
;
_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
_cell_angle_alpha                100.076(2)
_cell_angle_beta                 95.427(2)
_cell_angle_gamma                98.737(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5668(4)
_cell_length_b                   11.9743(5)
_cell_length_c                   13.3768(6)
_cell_measurement_reflns_used    6560
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1479.64(11)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction        'HKL Denzo and Scalepack'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0744
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10043
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.136
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         6757
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.1416
_refine_ls_R_factor_gt           0.0629
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0609P)²+0.7973P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1380
_refine_ls_wR_factor_ref         0.1884
_reflns_number_gt                3464
_reflns_number_total             6757
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802792j_si_001.cif
_cod_data_source_block           import
_cod_database_code               4024598
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C24 C 0.2661(7) 0.6266(5) 0.1011(5) 0.134(2) Uani 1 1 d . . .
H24A H 0.2242 0.6673 0.0536 0.101 Uiso 1 1 calc R . .
H24B H 0.3654 0.6292 0.0938 0.101 Uiso 1 1 calc R . .
H24C H 0.2563 0.6620 0.1696 0.101 Uiso 1 1 calc R . .
H18 H 0.083(3) 0.335(2) 0.1488(19) 0.032(7) Uiso 1 1 d . . .
S1 S 0.21380(10) 0.90342(8) 0.78311(7) 0.0582(3) Uani 1 1 d . . .
F2 F 0.3938(2) 0.7593(2) 0.78674(19) 0.0864(7) Uani 1 1 d . . .
O4 O 0.1984(3) 0.8719(2) 0.67497(18) 0.0836(8) Uani 1 1 d . . .
C31 C 0.2780(4) 0.7843(3) 0.8270(3) 0.0604(9) Uani 1 1 d . . .
F3 F 0.3078(3) 0.8028(2) 0.92752(18) 0.1005(8) Uani 1 1 d . . .
O5 O 0.0859(3) 0.9107(3) 0.8289(2) 0.0789(8) Uani 1 1 d . . .
O6 O 0.3283(3) 0.9976(2) 0.8268(2) 0.0765(8) Uani 1 1 d . . .
F1 F 0.1825(3) 0.6867(2) 0.8010(2) 0.0998(8) Uani 1 1 d . . .
O3 O 0.2581(2) 0.44621(19) 0.15279(16) 0.0560(6) Uani 1 1 d . . .
O2 O -0.1099(3) 0.7592(2) 0.34737(18) 0.0683(7) Uani 1 1 d . . .
C7 C 0.2086(3) 0.5184(3) 0.4806(2) 0.0462(7) Uani 1 1 d . . .
C1 C 0.2454(3) 0.3701(3) 0.3498(2) 0.0427(7) Uani 1 1 d . . .
N1 N 0.2428(3) 0.1482(2) 0.1310(2) 0.0523(7) Uani 1 1 d . . .
O1 O -0.0968(3) 0.6346(2) 0.2051(2) 0.0850(9) Uani 1 1 d . . .
C3 C 0.0842(3) 0.5222(3) 0.3165(2) 0.0480(8) Uani 1 1 d . . .
H3 H 0.0582 0.4914 0.2473 0.058 Uiso 1 1 calc R . .
C4 C 0.0305(3) 0.6182(3) 0.3621(2) 0.0487(8) Uani 1 1 d . . .
C17 C 0.2544(3) 0.1827(3) 0.2300(2) 0.0461(7) Uani 1 1 d . . .
C2 C 0.1763(3) 0.4727(3) 0.3748(2) 0.0441(7) Uani 1 1 d . . .
C16 C 0.2321(3) 0.3010(3) 0.2556(2) 0.0441(7) Uani 1 1 d . . .
C5 C 0.0675(4) 0.6635(3) 0.4656(3) 0.0539(8) Uani 1 1 d . . .
H5 H 0.0330 0.7285 0.4951 0.065 Uiso 1 1 calc R . .
C12 C 0.3723(4) 0.4687(3) 0.6240(3) 0.0590(9) Uani 1 1 d . . .
H12 H 0.3522 0.5254 0.6750 0.071 Uiso 1 1 calc R . .
C14 C -0.0640(4) 0.6694(3) 0.2954(3) 0.0574(9) Uani 1 1 d . . .
C30 C 0.1693(3) 0.0888(3) 0.3686(3) 0.0530(8) Uani 1 1 d . . .
H30 H 0.0941 0.1298 0.3692 0.064 Uiso 1 1 calc R . .
C8 C 0.3289(3) 0.3629(3) 0.4482(2) 0.0455(7) Uani 1 1 d . . .
C25 C 0.2685(3) 0.1021(3) 0.3008(2) 0.0466(8) Uani 1 1 d . . .
C13 C 0.3040(3) 0.4507(3) 0.5252(2) 0.0473(8) Uani 1 1 d . . .
C26 C 0.3798(4) 0.0394(3) 0.3003(3) 0.0566(9) Uani 1 1 d . . .
H26 H 0.4456 0.0465 0.2539 0.068 Uiso 1 1 calc R . .
C18 C 0.1856(4) 0.3352(3) 0.1547(2) 0.0474(8) Uani 1 1 d . . .
C9 C 0.4334(4) 0.2985(3) 0.4702(3) 0.0547(9) Uani 1 1 d . . .
H9 H 0.4563 0.2432 0.4193 0.066 Uiso 1 1 calc R . .
C19 C 0.2188(3) 0.2389(3) 0.0706(2) 0.0514(8) Uani 1 1 d . . .
C6 C 0.1552(4) 0.6129(3) 0.5254(3) 0.0546(9) Uani 1 1 d . . .
H6 H 0.1780 0.6423 0.5952 0.066 Uiso 1 1 calc R . .
C10 C 0.5032(4) 0.3180(3) 0.5694(3) 0.0600(9) Uani 1 1 d . . .
H10 H 0.5725 0.2747 0.5846 0.072 Uiso 1 1 calc R . .
C15 C -0.1996(5) 0.8185(4) 0.2896(3) 0.0856(13) Uani 1 1 d . . .
H15A H -0.2262 0.8810 0.3349 0.128 Uiso 1 1 calc R . .
H15B H -0.2837 0.7657 0.2566 0.128 Uiso 1 1 calc R . .
H15C H -0.1483 0.8480 0.2388 0.128 Uiso 1 1 calc R . .
C27 C 0.3920(4) -0.0331(3) 0.3689(3) 0.0698(11) Uani 1 1 d . . .
H27 H 0.4673 -0.0739 0.3695 0.084 Uiso 1 1 calc R . .
C22 C 0.0919(4) 0.1951(3) -0.0118(3) 0.0692(11) Uani 1 1 d . . .
H22A H 0.0082 0.1739 0.0196 0.104 Uiso 1 1 calc R . .
H22B H 0.1100 0.1291 -0.0576 0.104 Uiso 1 1 calc R . .
H22C H 0.0775 0.2546 -0.0494 0.104 Uiso 1 1 calc R . .
C11 C 0.4715(4) 0.4001(3) 0.6451(3) 0.0639(10) Uani 1 1 d . . .
H11 H 0.5170 0.4097 0.7114 0.077 Uiso 1 1 calc R . .
C29 C 0.1830(4) 0.0142(3) 0.4353(3) 0.0697(11) Uani 1 1 d . . .
H29 H 0.1157 0.0043 0.4803 0.084 Uiso 1 1 calc R . .
C23 C 0.1914(5) 0.5028(4) 0.0795(3) 0.0746(11) Uani 1 1 d . . .
H23A H 0.0909 0.4991 0.0864 0.090 Uiso 1 1 calc R . .
H23B H 0.2007 0.4660 0.0104 0.090 Uiso 1 1 calc R . .
C21 C 0.3543(4) 0.2741(4) 0.0244(3) 0.0755(11) Uani 1 1 d . . .
H21A H 0.4325 0.3006 0.0780 0.113 Uiso 1 1 calc R . .
H21B H 0.3419 0.3347 -0.0122 0.113 Uiso 1 1 calc R . .
H21C H 0.3740 0.2090 -0.0217 0.113 Uiso 1 1 calc R . .
C28 C 0.2941(5) -0.0454(4) 0.4364(3) 0.0763(11) Uani 1 1 d . . .
H28 H 0.3032 -0.0942 0.4827 0.092 Uiso 1 1 calc R . .
C20 C 0.2494(5) 0.0312(3) 0.0781(3) 0.0820(13) Uani 1 1 d . . .
H20A H 0.2387 0.0279 0.0055 0.123 Uiso 1 1 calc R . .
H20B H 0.1740 -0.0222 0.0950 0.123 Uiso 1 1 calc R . .
H20C H 0.3396 0.0113 0.0991 0.123 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'
F F 0.0171 0.0103 '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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 S1 O5 116.54(18) . . ?
O4 S1 O6 114.93(18) . . ?
O5 S1 O6 113.28(17) . . ?
O4 S1 C31 104.26(17) . . ?
O5 S1 C31 103.78(18) . . ?
O6 S1 C31 101.62(17) . . ?
F3 C31 F2 107.7(3) . . ?
F3 C31 F1 106.2(3) . . ?
F2 C31 F1 104.9(3) . . ?
F3 C31 S1 112.5(3) . . ?
F2 C31 S1 112.7(3) . . ?
F1 C31 S1 112.3(3) . . ?
C18 O3 C23 114.3(3) . . ?
C14 O2 C15 117.0(3) . . ?
C6 C7 C2 121.4(3) . . ?
C6 C7 C13 130.3(3) . . ?
C2 C7 C13 108.3(3) . . ?
C16 C1 C2 125.2(3) . . ?
C16 C1 C8 129.8(3) . . ?
C2 C1 C8 105.0(2) . . ?
C17 N1 C20 125.6(3) . . ?
C17 N1 C19 114.4(3) . . ?
C20 N1 C19 120.0(3) . . ?
C2 C3 C4 119.9(3) . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 C14 122.3(3) . . ?
C3 C4 C14 117.4(3) . . ?
N1 C17 C16 110.9(3) . . ?
N1 C17 C25 121.4(3) . . ?
C16 C17 C25 127.2(3) . . ?
C3 C2 C7 118.6(3) . . ?
C3 C2 C1 132.3(3) . . ?
C7 C2 C1 109.0(3) . . ?
C1 C16 C17 128.6(3) . . ?
C1 C16 C18 125.2(3) . . ?
C17 C16 C18 106.3(3) . . ?
C6 C5 C4 120.5(3) . . ?
C11 C12 C13 118.3(3) . . ?
O1 C14 O2 123.3(3) . . ?
O1 C14 C4 124.7(3) . . ?
O2 C14 C4 112.0(3) . . ?
C25 C30 C29 119.4(3) . . ?
C9 C8 C13 118.7(3) . . ?
C9 C8 C1 132.0(3) . . ?
C13 C8 C1 108.6(3) . . ?
C30 C25 C26 119.6(3) . . ?
C30 C25 C17 119.3(3) . . ?
C26 C25 C17 121.1(3) . . ?
C12 C13 C8 121.8(3) . . ?
C12 C13 C7 129.0(3) . . ?
C8 C13 C7 109.1(3) . . ?
C27 C26 C25 119.7(3) . . ?
O3 C18 C16 109.6(2) . . ?
O3 C18 C19 114.1(3) . . ?
C16 C18 C19 104.9(3) . . ?
C8 C9 C10 119.2(3) . . ?
N1 C19 C22 110.6(3) . . ?
N1 C19 C21 108.5(3) . . ?
C22 C19 C21 111.4(3) . . ?
N1 C19 C18 101.4(2) . . ?
C22 C19 C18 111.0(3) . . ?
C21 C19 C18 113.5(3) . . ?
C7 C6 C5 119.2(3) . . ?
C11 C10 C9 121.1(3) . . ?
C28 C27 C26 120.5(4) . . ?
C10 C11 C12 120.8(3) . . ?
C28 C29 C30 121.0(4) . . ?
O3 C23 C24 107.1(3) . . ?
C29 C28 C27 119.8(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C24 C23 1.510(6) . ?
S1 O4 1.417(2) . ?
S1 O5 1.427(3) . ?
S1 O6 1.445(3) . ?
S1 C31 1.802(4) . ?
F2 C31 1.328(4) . ?
C31 F3 1.319(4) . ?
C31 F1 1.340(4) . ?
O3 C18 1.409(4) . ?
O3 C23 1.440(4) . ?
O2 C14 1.331(4) . ?
O2 C15 1.446(4) . ?
C7 C6 1.376(4) . ?
C7 C2 1.412(4) . ?
C7 C13 1.463(4) . ?
C1 C16 1.364(4) . ?
C1 C2 1.485(4) . ?
C1 C8 1.496(4) . ?
N1 C17 1.306(4) . ?
N1 C20 1.468(4) . ?
N1 C19 1.494(4) . ?
O1 C14 1.201(4) . ?
C3 C2 1.387(4) . ?
C3 C4 1.397(4) . ?
C4 C5 1.387(4) . ?
C4 C14 1.482(5) . ?
C17 C16 1.451(4) . ?
C17 C25 1.477(4) . ?
C16 C18 1.523(4) . ?
C5 C6 1.382(5) . ?
C12 C11 1.387(5) . ?
C12 C13 1.384(4) . ?
C30 C25 1.385(4) . ?
C30 C29 1.380(5) . ?
C8 C9 1.392(4) . ?
C8 C13 1.402(4) . ?
C25 C26 1.392(4) . ?
C26 C27 1.379(5) . ?
C18 C19 1.556(4) . ?
C9 C10 1.392(4) . ?
C19 C22 1.522(5) . ?
C19 C21 1.522(5) . ?
C10 C11 1.373(5) . ?
C27 C28 1.370(5) . ?
C29 C28 1.368(5) . ?
