#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:07:49 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180223 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/09/7110906.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7110906
loop_
_publ_author_name
'Asiri, Abdullah M. A.'
'Heller, Harry G.'
'Hursthouse, Michael B.'
'Karalulov, Alexander'
_publ_section_title
;
 Tribochromic compounds, exemplified by
 3-dicyclopropylmethylene-5-dicyanomethylene-4-diphenylmethylenetetrahydrofuran-2-one
;
_journal_issue                   9
_journal_name_full               'Chemical Communications'
_journal_page_first              799
_journal_paper_doi               10.1039/b001567i
_journal_year                    2000
_chemical_formula_sum            'C27 H20 N2 O2'
_chemical_formula_weight         404.45
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 110.38(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.066(26)
_cell_length_b                   23.906(52)
_cell_length_c                   9.504(47)
_cell_measurement_temperature    293(2)
_cell_volume                     2144(13)
_computing_structure_refinement  'SHELXL-92 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.1286
_diffrn_reflns_av_sigmaI/netI    0.7940
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6027
_diffrn_reflns_theta_max         24.65
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.080
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_F_000             848
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   0.750
_refine_ls_goodness_of_fit_obs   1.557
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         2629
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.750
_refine_ls_restrained_S_obs      1.557
_refine_ls_R_factor_all          0.2377
_refine_ls_R_factor_obs          0.0897
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2440
_refine_ls_wR_factor_obs         0.2076
_reflns_number_observed          636
_reflns_number_total             2629
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            b001567isup1.cif
_cod_data_source_block           s92-2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        2143.9(129)
_cod_database_code               7110906
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.2115(7) 0.4955(3) 0.5008(7) 0.071(2) Uani 1 d .
O2 O 0.0056(7) 0.4609(3) 0.3473(8) 0.079(2) Uani 1 d .
N1 N 0.5325(9) 0.4513(4) 0.7299(11) 0.104(4) Uani 1 d .
N2 N 0.5845(8) 0.6291(4) 0.6348(10) 0.083(3) Uani 1 d .
C1 C 0.4166(10) 0.5455(4) 0.6095(12) 0.067(3) Uani 1 d .
C2 C 0.2791(10) 0.5443(4) 0.5286(11) 0.064(3) Uani 1 d .
C3 C 0.1807(9) 0.5907(4) 0.4512(11) 0.059(3) Uani 1 d .
C4 C 0.0702(10) 0.5586(3) 0.3340(12) 0.052(3) Uani 1 d .
C5 C 0.0823(9) 0.5004(4) 0.3854(11) 0.054(3) Uani 1 d .
C6 C 0.4853(12) 0.4936(5) 0.6779(13) 0.089(4) Uani 1 d .
C7 C 0.5089(11) 0.5910(5) 0.6267(12) 0.069(3) Uani 1 d .
C8 C 0.1684(10) 0.6423(4) 0.5065(11) 0.057(3) Uani 1 d .
C9 C 0.2652(6) 0.6631(3) 0.6525(7) 0.060(3) Uani 1 d G
C10 C 0.2884(7) 0.6308(2) 0.7803(10) 0.066(3) Uani 1 d G
H10 H 0.2414(11) 0.5968(3) 0.7738(15) 0.079 Uiso 1 calc R
C11 C 0.3820(8) 0.6490(4) 0.9180(7) 0.087(4) Uani 1 d G
H11 H 0.3976(12) 0.6274(5) 1.0035(9) 0.104 Uiso 1 calc R
C12 C 0.4524(6) 0.6997(4) 0.9278(8) 0.104(5) Uani 1 d G
H12 H 0.5150(9) 0.7120(6) 1.0199(10) 0.125 Uiso 1 calc R
C13 C 0.4291(7) 0.7321(3) 0.8000(12) 0.093(4) Uani 1 d G
H13 H 0.4762(10) 0.7660(3) 0.8066(17) 0.112 Uiso 1 calc R
C14 C 0.3355(8) 0.7138(3) 0.6624(9) 0.075(4) Uani 1 d G
H14 H 0.3200(12) 0.7355(4) 0.5768(11) 0.090 Uiso 1 calc R
C15 C 0.0416(6) 0.6779(2) 0.4295(7) 0.058(3) Uani 1 d G
C16 C 0.0495(6) 0.7271(3) 0.3550(8) 0.075(3) Uani 1 d G
H16 H 0.1357(8) 0.7385(4) 0.3491(11) 0.090 Uiso 1 calc R
C17 C -0.0714(9) 0.7592(2) 0.2894(7) 0.089(4) Uani 1 d G
H17 H -0.0661(12) 0.7922(3) 0.2396(10) 0.106 Uiso 1 calc R
C18 C -0.2002(7) 0.7421(3) 0.2983(7) 0.087(4) Uani 1 d G
H18 H -0.2811(8) 0.7636(4) 0.2544(11) 0.105 Uiso 1 calc R
C19 C -0.2081(6) 0.6929(3) 0.3728(8) 0.095(4) Uani 1 d G
H19 H -0.2943(7) 0.6815(4) 0.3787(12) 0.114 Uiso 1 calc R
C20 C -0.0872(8) 0.6608(2) 0.4384(7) 0.073(3) Uani 1 d G
H20 H -0.0925(11) 0.6278(3) 0.4882(10) 0.088 Uiso 1 calc R
C21 C -0.0218(10) 0.5741(4) 0.1951(13) 0.069(3) Uani 1 d .
C22 C -0.1473(11) 0.5409(4) 0.1120(13) 0.098(5) Uani 1 d .
H22 H -0.1573(11) 0.5061(4) 0.1619(13) 0.165(17) Uiso 1 calc R
C23 C 0.0069(13) 0.6257(4) 0.1164(14) 0.078(3) Uani 1 d .
H23 H -0.0650(13) 0.6551(4) 0.0959(14) 0.165(17) Uiso 1 calc R
C24 C 0.0705(14) 0.6166(5) -0.0062(16) 0.115(5) Uani 1 d .
H24A H 0.0977(14) 0.5788(5) -0.0219(16) 0.165(17) Uiso 1 calc R
H24B H 0.0336(14) 0.6390(5) -0.0967(16) 0.165(17) Uiso 1 calc R
C25 C 0.1568(13) 0.6457(4) 0.1358(14) 0.106(4) Uani 1 d .
H25A H 0.1717(13) 0.6857(4) 0.1309(14) 0.165(17) Uiso 1 calc R
H25B H 0.2359(13) 0.6255(4) 0.2057(14) 0.165(17) Uiso 1 calc R
C26 C -0.2041(15) 0.5389(5) -0.0437(18) 0.154(7) Uani 1 d .
H26A H -0.2421(15) 0.5033(5) -0.0893(18) 0.165(17) Uiso 1 calc R
H26B H -0.1561(15) 0.5601(5) -0.0987(18) 0.165(17) Uiso 1 calc R
C27 C -0.2860(11) 0.5697(5) 0.0270(14) 0.111(5) Uani 1 d .
H27A H -0.3729(11) 0.5530(5) 0.0298(14) 0.165(17) Uiso 1 calc R
H27B H -0.2865(11) 0.6102(5) 0.0203(14) 0.165(17) Uiso 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 O1 C5 111.0(7)
C2 C1 C7 126.7(10)
C2 C1 C6 118.4(10)
C7 C1 C6 114.6(9)
C1 C2 O1 119.4(10)
C1 C2 C3 130.2(10)
O1 C2 C3 110.3(8)
C8 C3 C4 127.7(8)
C8 C3 C2 127.9(9)
C4 C3 C2 100.4(8)
C21 C4 C5 121.7(8)
C21 C4 C3 131.4(8)
C5 C4 C3 106.7(8)
O2 C5 O1 120.2(9)
O2 C5 C4 132.9(9)
O1 C5 C4 106.9(7)
N1 C6 C1 176.4(14)
N2 C7 C1 177.2(12)
C3 C8 C9 123.3(8)
C3 C8 C15 120.2(8)
C9 C8 C15 116.0(7)
C10 C9 C14 120.0
C10 C9 C8 119.3(7)
C14 C9 C8 120.7(7)
C11 C10 C9 120.0
C10 C11 C12 120.0
C13 C12 C11 120.0
C12 C13 C14 120.0
C13 C14 C9 120.0
C16 C15 C20 120.0
C16 C15 C8 122.7(6)
C20 C15 C8 117.3(6)
C15 C16 C17 120.0
C18 C17 C16 120.0
C19 C18 C17 120.0
C18 C19 C20 120.0
C19 C20 C15 120.0
C4 C21 C22 122.5(10)
C4 C21 C23 120.7(9)
C22 C21 C23 116.7(10)
C26 C22 C21 123.4(13)
C26 C22 C27 59.1(8)
C21 C22 C27 120.2(10)
C21 C23 C24 117.5(10)
C21 C23 C25 122.9(9)
C24 C23 C25 58.7(8)
C25 C24 C23 60.8(9)
C24 C25 C23 60.6(8)
C22 C26 C27 64.8(11)
C26 C27 C22 56.1(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.330(10)
O1 C5 1.384(10)
O2 C5 1.194(8)
N1 C6 1.153(11)
N2 C7 1.170(11)
C1 C2 1.329(11)
C1 C7 1.403(13)
C1 C6 1.459(13)
C2 C3 1.498(12)
C3 C8 1.364(12)
C3 C4 1.484(12)
C4 C21 1.373(13)
C4 C5 1.466(11)
C8 C9 1.477(11)
C8 C15 1.495(10)
C9 C10 1.39
C9 C14 1.39
C10 C11 1.39
C11 C12 1.39
C12 C13 1.39
C13 C14 1.39
C15 C16 1.39
C15 C20 1.39
C16 C17 1.39
C17 C18 1.39
C18 C19 1.39
C19 C20 1.39
C21 C22 1.467(13)
C21 C23 1.521(14)
C22 C26 1.39(2)
C22 C27 1.514(14)
C23 C24 1.53(2)
C23 C25 1.53(2)
C24 C25 1.50(2)
C26 C27 1.44(2)
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
C7 C1 C2 O1 167.7(10)
C6 C1 C2 O1 -6.2(15)
C7 C1 C2 C3 -8.7(18)
C6 C1 C2 C3 177.4(10)
C5 O1 C2 C1 -164.3(9)
C5 O1 C2 C3 12.8(10)
C1 C2 C3 C8 -45.5(17)
O1 C2 C3 C8 137.8(10)
C1 C2 C3 C4 155.9(11)
O1 C2 C3 C4 -20.7(10)
C8 C3 C4 C21 47.9(17)
C2 C3 C4 C21 -153.5(10)
C8 C3 C4 C5 -138.0(10)
C2 C3 C4 C5 20.6(9)
C2 O1 C5 O2 -178.4(9)
C2 O1 C5 C4 1.4(10)
C21 C4 C5 O2 -20.2(18)
C3 C4 C5 O2 165.0(11)
C21 C4 C5 O1 160.0(8)
C3 C4 C5 O1 -14.8(10)
C2 C1 C6 N1 -10.1(214)
C7 C1 C6 N1 175.3(206)
C2 C1 C7 N2 -58.1(238)
C6 C1 C7 N2 116.0(234)
C4 C3 C8 C9 159.7(9)
C2 C3 C8 C9 6.8(16)
C4 C3 C8 C15 -11.7(16)
C2 C3 C8 C15 -164.6(8)
C3 C8 C9 C10 -52.4(11)
C15 C8 C9 C10 119.4(7)
C3 C8 C9 C14 125.9(9)
C15 C8 C9 C14 -62.3(9)
C14 C9 C10 C11 0.0
C8 C9 C10 C11 178.3(6)
C9 C10 C11 C12 0.0
C10 C11 C12 C13 0.0
C11 C12 C13 C14 0.0
C12 C13 C14 C9 0.0
C10 C9 C14 C13 0.0
C8 C9 C14 C13 -178.3(6)
C3 C8 C15 C16 -111.7(9)
C9 C8 C15 C16 76.2(9)
C3 C8 C15 C20 70.1(11)
C9 C8 C15 C20 -101.9(8)
C20 C15 C16 C17 0.0
C8 C15 C16 C17 -178.1(7)
C15 C16 C17 C18 0.0
C16 C17 C18 C19 0.0
C17 C18 C19 C20 0.0
C18 C19 C20 C15 0.0
C16 C15 C20 C19 0.0
C8 C15 C20 C19 178.2(7)
C5 C4 C21 C22 22.9(15)
C3 C4 C21 C22 -163.7(10)
C5 C4 C21 C23 -154.0(10)
C3 C4 C21 C23 19.4(16)
C4 C21 C22 C26 -149.9(12)
C23 C21 C22 C26 27.2(16)
C4 C21 C22 C27 139.3(12)
C23 C21 C22 C27 -43.7(17)
C4 C21 C23 C24 100.5(13)
C22 C21 C23 C24 -76.6(14)
C4 C21 C23 C25 31.7(17)
C22 C21 C23 C25 -145.4(11)
C21 C23 C24 C25 -113.5(11)
C25 C23 C24 C25 0.000(2)
C23 C24 C25 C23 0.000(2)
C21 C23 C25 C24 104.5(13)
C24 C23 C25 C24 0.000(2)
C21 C22 C26 C27 -107.9(14)
C27 C22 C26 C27 0.000(4)
C22 C26 C27 C22 0.000(6)
C26 C22 C27 C26 0.000(4)
C21 C22 C27 C26 113.2(16)
