#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006294.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2006294
loop_
_publ_author_name
'Yao, C.-F.'
'Chen, Y.-S.'
'Chen, W.-C.'
'Sheu, R.-S.'
'Lai, J.-K.'
'Ueng, C.-H.'
_publ_section_title
;
 1,3-Diphenyl-2-tricyclo[3.3.1.1^3,7^]dec-2-ylidenepropane-1,3-diimine,
 and its -1-imino-3-one and -1,3-dione Derivatives
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              956
_journal_page_last               959
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety         'C25 H25 N O'
_chemical_formula_sum            'C25 H25 N O'
_chemical_formula_weight         355.48
_chemical_name_systematic
'1,3-Diphenyl-2-tricyclo[3,3,1,1^3,7^]dec -2-ylidenepropane-1-imino-3-one'
_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'
_cell_angle_alpha                90
_cell_angle_beta                 106.360(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1960(10)
_cell_length_b                   15.4780(10)
_cell_length_c                   12.664(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.90
_cell_measurement_theta_min      20.94
_cell_volume                     1917.6(5)
_computing_cell_refinement       NONIUS
_computing_data_collection       'NONIUS (Riche, 1989)'
_computing_data_reduction        'NRCVAX (Larson et al., 1990)'
_computing_molecular_graphics    'ORTEP (Johnson, 1965)'
_computing_publication_material  NRCVAX
_computing_structure_refinement  NRCVAX
_computing_structure_solution    NRCVAX
_diffrn_ambient_temperature      298
_diffrn_measurement_device       ' CAD-4 diffractometer '
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         x-ray_tube
_diffrn_radiation_type           ' Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0084
_diffrn_reflns_av_sigmaI/netI    0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3531
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         1.5
_diffrn_standards_decay_%        3
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.07
_exptl_absorpt_correction_T_max  .998
_exptl_absorpt_correction_T_min  .955
_exptl_absorpt_correction_type
'empirical \y scans (North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       tetragonal
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         .180
_refine_diff_density_min         -.250
_refine_ls_extinction_coef       0.137631
_refine_ls_extinction_method     secondary
_refine_ls_goodness_of_fit_obs   2.80
_refine_ls_hydrogen_treatment
; H atoms calcutated, except those in N-H which were found from a \DF map
 and not refined
;
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2085
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          .080
_refine_ls_R_factor_obs          .043
_refine_ls_shift/esd_max         0
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      1/\s^2^(F)
_refine_ls_wR_factor_all         .034
_refine_ls_wR_factor_obs         .033
_reflns_number_observed          2085
_reflns_number_total             3367
_reflns_observed_criterion       I>2.5\sI
_[local]_cod_data_source_file    de1050.cif
_[local]_cod_data_source_block   2
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1917.7(5)
_cod_database_code               2006294
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,1/2+y,1/2-z
x,1/2-y,1/2+z
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
_atom_site_aniso_type_symbol
O 8.2(2) 21.6(3) 6.6(2) 0.6(2) 0.70(10) 4.2(2) O
N 11.1(2) 7.7(2) 3.70(10) 1.1(2) 0.20(10) -1.00(10) N
C1 4.3(2) 6.5(2) 3.60(10) -0.30(10) 1.10(10) 0.20(10) C
C2 4.30(10) 6.0(2) 4.00(10) 0.20(10) 1.50(10) 0.40(10) C
C3 4.7(2) 6.1(2) 6.1(2) 0.80(10) 1.60(10) -0.2(2) C
C4 7.2(2) 6.3(2) 6.3(2) 0.20(10) 2.9(2) -1.1(2) C
C5 6.6(2) 6.9(2) 5.0(2) -0.7(2) 1.10(10) -1.0(2) C
C6 4.9(2) 6.4(2) 5.6(2) -0.30(10) 0.60(10) 0.20(10) C
C7 4.10(10) 5.0(2) 5.7(2) 0.00(10) 1.50(10) -0.10(10) C
C8 5.4(2) 6.2(2) 6.6(2) -0.80(10) 2.50(10) -0.1(2) C
C9 7.4(2) 5.2(2) 7.1(2) -0.7(2) 2.8(2) 0.5(2) C
C10 7.4(2) 5.7(2) 8.6(2) -1.0(2) 2.4(2) -1.3(2) C
C11 7.4(2) 5.9(2) 7.2(2) 1.4(2) 2.0(2) 1.1(2) C
C12 5.2(2) 8.4(2) 4.0(2) -0.10(10) 0.40(10) 0.20(10) C
C13 5.5(2) 6.2(2) 4.8(2) -1.20(10) 1.60(10) -0.40(10) C
C1A 4.2(2) 5.3(2) 5.5(2) 0.20(10) 1.30(10) -0.50(10) C
C2A 4.8(2) 6.8(2) 5.9(2) 0.10(10) 1.80(10) 0.1(2) C
C3A 6.7(2) 7.8(2) 7.6(2) 1.3(2) 3.5(2) 1.1(2) C
C4A 5.9(2) 8.4(2) 11.9(3) 1.5(2) 4.8(2) 1.7(2) C
C5A 3.9(2) 9.3(2) 11.5(3) 0.3(2) 2.0(2) -0.3(2) C
C6A 4.4(2) 7.7(2) 7.0(2) 0.80(10) 0.60(10) -0.8(2) C
C1B 4.8(2) 5.4(2) 5.5(2) -1.10(10) 1.60(10) -0.50(10) C
C2B 6.4(2) 8.1(2) 7.6(2) -0.1(2) 2.7(2) -1.1(2) C
C3B 7.2(2) 8.9(3) 12.5(3) 1.9(2) 2.7(2) -1.2(3) C
C4B 7.8(2) 7.9(3) 11.8(3) 1.3(2) 0.0(2) 1.6(3) C
C5B 8.9(2) 7.4(2) 6.9(2) 0.0(2) 0.7(2) 1.2(2) C
C6B 6.2(2) 5.7(2) 5.6(2) -0.30(10) 1.30(10) 0.2(2) C
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_thermal_displace_type
_atom_site_type_symbol
O 0.3343(2) 0.8956(2) 0.0453(2) Uij O
N 0.5391(2) 0.7468(2) 0.0490(2) Uij N
C1 0.5278(2) 0.8498(2) 0.1877(2) Uij C
C2 0.6100(2) 0.9105(2) 0.2447(2) Uij C
C3 0.5605(2) 0.9964(2) 0.2762(2) Uij C
C4 0.6215(3) 1.0110(2) 0.4006(2) Uij C
C5 0.7782(3) 1.0105(2) 0.4293(2) Uij C
C6 0.8259(2) 0.9227(2) 0.3992(2) Uij C
C7 0.7647(2) 0.90660(10) 0.2751(2) Uij C
C8 0.8125(2) 0.9786(2) 0.2106(2) Uij C
C9 0.7663(3) 1.0663(2) 0.2418(2) Uij C
C10 0.8259(3) 1.0817(2) 0.3652(2) Uij C
C11 0.6105(3) 1.0680(2) 0.2133(2) Uij C
C12 0.3769(3) 0.8651(2) 0.1392(2) Uij C
C13 0.5756(2) 0.7677(2) 0.1478(2) Uij C
C1A 0.2784(2) 0.8385(2) 0.1993(2) Uij C
C2A 0.3184(2) 0.8235(2) 0.3111(2) Uij C
C3A 0.2244(3) 0.7981(2) 0.3654(2) Uij C
C4A 0.0906(3) 0.7863(2) 0.3073(3) Uij C
C5A 0.0495(3) 0.8002(2) 0.1957(3) Uij C
C6A 0.1417(3) 0.8272(2) 0.1411(2) Uij C
C1B 0.6656(2) 0.7066(2) 0.2266(2) Uij C
C2B 0.7339(3) 0.6423(2) 0.1869(2) Uij C
C3B 0.8132(3) 0.5829(2) 0.2568(3) Uij C
C4B 0.8258(3) 0.5856(2) 0.3677(3) Uij C
C5B 0.7586(3) 0.6485(2) 0.4081(2) Uij C
C6B 0.6793(3) 0.7088(2) 0.3384(2) Uij C
HN 0.491 0.793 -0.001 Uij H
H3 0.450 0.997 0.256 Uij H
H4 0.589 0.960 0.445 Uij H
H4' 0.588 1.072 0.423 Uij H
H5 0.821 1.022 0.517 Uij H
H6 0.936 0.922 0.419 Uij H
H6' 0.792 0.873 0.445 Uij H
H7 0.798 0.844 0.253 Uij H
H8 0.769 0.968 0.123 Uij H
H8' 0.923 0.977 0.230 Uij H
H9 0.801 1.117 0.197 Uij H
H10 0.792 1.144 0.387 Uij H
H10' 0.936 1.081 0.386 Uij H
H11 0.578 1.130 0.235 Uij H
H11' 0.568 1.058 0.126 Uij H
H2A 0.415 0.830 0.353 Uij H
H3A 0.253 0.789 0.445 Uij H
H4A 0.024 0.768 0.345 Uij H
H5A -0.046 0.792 0.154 Uij H
H6A 0.111 0.838 0.061 Uij H
H2B 0.725 0.639 0.108 Uij H
H3B 0.862 0.538 0.228 Uij H
H4B 0.882 0.542 0.417 Uij H
H5B 0.767 0.650 0.487 Uij H
H6B 0.632 0.754 0.369 Uij H
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C .017 .009 International_Tables_Vol_IV_Table_2.3.1
H 0 0 International_Tables_Vol_IV_Table_2.3.1
O .047 .032 International_Tables_Vol_IV_Table_2.3.1
N .029 .018 International_Tables_Vol_IV_Table_2.3.1
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-6 0 2
-3 -6 4
0 8 2
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C13 N HN 114.0(2) ?
C2 C1 C12 121.7(2) yes
C2 C1 C13 124.6(2) yes
C12 C1 C13 112.8(2) yes
C1 C2 C3 123.9(2) ?
C1 C2 C7 124.2(2) ?
C3 C2 C7 111.6(2) ?
C2 C3 C4 109.3(2) ?
C2 C3 C11 108.3(2) ?
C2 C3 H3 110.4(2) ?
C4 C3 C11 109.2(2) ?
C4 C3 H3 109.8(2) ?
C11 C3 H3 110.0(2) ?
C3 C4 C5 109.5(2) ?
C3 C4 H4 109.4(2) ?
C3 C4 H4' 109.5(2) ?
C5 C4 H4 109.2(2) ?
C5 C4 H4' 109.3(2) ?
H4 C4 H4' 109.9(2) ?
C4 C5 C6 109.2(2) ?
C4 C5 C10 109.7(2) ?
C4 C5 H5 109.2(2) ?
C6 C5 C10 109.7(2) ?
C6 C5 H5 109.5(2) ?
C10 C5 H5 109.5(2) ?
C5 C6 C7 109.4(2) ?
C5 C6 H6 109.5(2) ?
C5 C6 H6' 109.4(2) ?
C7 C6 H6 109.6(2) ?
C7 C6 H6' 109.5(2) ?
H6 C6 H6' 109.4(2) ?
C2 C7 C6 110.3(2) ?
C2 C7 H7 110.2(2) ?
C2 C7 C8 107.4(2) ?
C6 C7 C8 109.1(2) ?
C6 C7 H7 109.9(2) ?
C8 C7 H7 109.9(2) ?
C7 C8 C9 109.9(2) ?
C7 C8 H8 109.4(2) ?
C7 C8 H8' 109.4(2) ?
C9 C8 H8 109.4(2) ?
C9 C8 H8' 109.4(2) ?
H8 C8 H8' 109.4(2) ?
C8 C9 C10 109.9(2) ?
C8 C9 C11 109.3(2) ?
C8 C9 H9 109.6(2) ?
C10 C9 C11 109.1(2) ?
C10 C9 H9 109.4(2) ?
C11 C9 H9 109.6(2) ?
C5 C10 C9 109.7(2) ?
C5 C10 H10 109.4(2) ?
C5 C10 H10' 109.3(2) ?
C9 C10 H10 109.6(2) ?
C9 C10 H10' 109.5(2) ?
H10 C10 H10' 109.5(2) ?
C3 C11 C9 110.0(2) ?
C3 C11 H11 109.6(2) ?
C3 C11 H11' 109.4(2) ?
C9 C11 H11 109.3(2) ?
C9 C11 H11' 109.2(2) ?
H11 C11 H11' 109.4(2) ?
O C12 C1 119.5(2) yes
O C12 C1A 119.7(2) ?
C1 C12 C1A 120.7(2) ?
N C13 C1 121.7(2) yes
N C13 C1B 117.6(2) ?
C1 C13 C1B 120.7(2) ?
C12 C1A C2A 121.9(2) ?
C12 C1A C6A 119.1(2) ?
C2A C1A C6A 119.0(2) ?
C1A C2A C3A 120.8(2) ?
C1A C2A H2A 119.6(2) ?
C3A C2A H2A 119.7(3) ?
C2A C3A C4A 119.7(3) ?
C2A C3A H3A 120.2(3) ?
C4A C3A H3A 120.1(3) ?
C3A C4A C5A 120.1(3) ?
C3A C4A H4A 120.0(3) ?
C5A C4A H4A 119.9(3) ?
C4A C5A C6A 120.7(2) ?
C4A C5A H5A 120.2(3) ?
C6A C5A H5A 119.1(3) ?
C1A C6A C5A 119.7(3) ?
C1A C6A H6A 120.2(3) ?
C5A C6A H6A 120.2(3) ?
C13 C1B C2B 119.3(2) ?
C13 C1B C6B 122.4(2) ?
C2B C1B C6B 118.2(2) ?
C1B C2B C3B 120.8(3) ?
C1B C2B H2B 119.9(3) ?
C3B C2B H2B 119.2(3) ?
C2B C3B C4B 120.5(3) ?
C2B C3B H3B 119.9(4) ?
C4B C3B H3B 119.6(4) ?
C3B C4B C5B 119.3(3) ?
C3B C4B H4B 120.1(4) ?
C5B C4B H4B 120.6(4) ?
C4B C5B C6B 120.5(3) ?
C4B C5B H5B 119.6(3) ?
C6B C5B H5B 119.9(3) ?
C1B C6B C5B 120.7(3) ?
C1B C6B H6B 119.7(2) ?
C5B C6B H6B 119.7(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O C12 1.239(3) yes
O HN 2.435(2) yes
N C13 1.243(3) yes
HN N 0.991(2) ?
C1 C2 1.329(3) yes
C1 C12 1.506(3) yes
C1 C13 1.499(4) yes
C2 C3 1.514(3) yes
C2 C7 1.516(3) yes
C3 C4 1.539(4) ?
C3 C11 1.533(4) ?
C3 H3 1.080(2) ?
C4 C5 1.535(4) ?
C4 H4 1.077(3) ?
C4 H4' 1.077(2) ?
C5 C6 1.528(4) ?
C5 C10 1.527(4) ?
C5 H5 1.086(2) ?
C6 C7 1.538(3) ?
C6 H6 1.080(2) ?
C6 H6' 1.081(2) ?
C7 C8 1.539(3) ?
C7 H7 1.082(2) ?
C8 C9 1.525(4) ?
C8 H8 1.081(2) ?
C8 H8' 1.081(2) ?
C9 C10 1.529(4) ?
C9 C11 1.526(4) ?
C9 H9 1.081(2) ?
C10 H10 1.079(3) ?
C10 H10' 1.080(3) ?
C11 H11 1.080(3) ?
C11 H11' 1.082(3) ?
C12 C1A 1.478(4) ?
C13 C1B 1.489(4) ?
C1A C2A 1.378(4) ?
C1A C6A 1.392(3) ?
C2A C3A 1.385(4) ?
C2A H2A 0.982(2) ?
C3A C4A 1.368(4) ?
C3A H3A 0.981(3) ?
C4A C5A 1.373(5) ?
C4A H4A 0.979(3) ?
C5A C6A 1.379(4) ?
C5A H5A 0.979(3) ?
C6A H6A 0.982(3) ?
C1B C2B 1.387(4) ?
C1B C6B 1.383(4) ?
C2B C3B 1.371(5) ?
C2B H2B 0.981(3) ?
C3B C4B 1.375(6) ?
C3B H3B 0.983(3) ?
C4B C5B 1.370(5) ?
C4B H4B 0.985(3) ?
C5B C6B 1.378(4) ?
C5B H5B 0.982(3) ?
C6B H6B 0.986(3) ?
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_publ_flag
C12 C1 C2 C3 6.10(10) ?
C13 C1 C2 C3 174.7(2) ?
C2 C1 C12 O 89.2(2) yes
C13 C1 C12 O -80.6(2) ?
C2 C1 C13 N -124.5(3) yes
C12 C1 C13 N 45.0(2) ?
C1 C2 C3 C4 128.5(2) ?
C7 C2 C3 C4 -57.9(2) ?
C1 C2 C7 C6 -128.9(2) ?
C3 C2 C7 C6 57.5(2) ?
C2 C3 C4 C5 59.3(2) ?
C2 C3 C11 C9 -58.9(2) ?
C3 C4 C5 C6 -61.0(2) ?
C4 C5 C6 C7 60.0(2) ?
C4 C5 C10 C9 -60.1(2) ?
C5 C6 C7 C2 -58.0(2) ?
C2 C7 C8 C9 60.2(2) ?
C7 C8 C9 C10 59.3(2) ?
C8 C9 C10 C5 -59.3(2) ?
C8 C9 C11 C3 59.5(2) ?
O C12 C1A C2A -164.5(3) ?
C1 C12 C1A C2A 19.70(10) ?
N C13 C1B C2B 16.90(10) ?
C1 C13 C1B C2B -165.0(3) ?
C12 C1A C2A C3A -179.5(3) ?
C12 C1A C6A C5A 178.2(3) ?
C1A C2A C3A C4A 1.00(10) ?
C3A C4A C5A C6A -1.00(10) ?
C13 C1B C2B C3B -177.4(3) ?
C13 C1B C6B C5B 176.9(3) ?
C1B C2B C3B C4B 0.5(2) ?
C3B C4B C5B C6B -0.1(2) ?
C12 C1 C2 C7 -166.8(2) ?
C13 C1 C2 C7 1.80(10) ?
C2 C1 C12 C1A -95.0(2) ?
C13 C1 C12 C1A 95.2(2) ?
C2 C1 C13 C1B 57.5(2) ?
C12 C1 C13 C1B -133.0(2) ?
C1 C2 C3 C11 -112.7(2) ?
C7 C2 C3 C11 60.9(2) ?
C1 C2 C7 C8 112.4(2) ?
C3 C2 C7 C8 -61.3(2) ?
C11 C3 C4 C5 -58.9(2) ?
C4 C3 C11 C9 59.9(2) ?
C10 C5 C6 C7 -60.3(2) ?
C6 C5 C10 C9 59.9(2) ?
C5 C6 C7 C8 59.7(2) ?
C6 C7 C8 C9 -59.4(2) ?
C7 C8 C9 C11 -60.4(2) ?
C11 C9 C10 C5 60.5(2) ?
C10 C9 C11 C3 -60.6(2) ?
O C12 C1A C6A 16.30(10) ?
C1 C12 C1A C6A -159.5(3) ?
N C13 C1B C6B -160.0(3) ?
C1 C13 C1B C6B 18.00(10) ?
C6A C1A C2A C3A -0.30(10) ?
C2A C1A C6A C5A -1.00(10) ?
C2A C3A C4A C5A -0.30(10) ?
C4A C5A C6A C1A 1.70(10) ?
C6B C1B C2B C3B -0.3(2) ?
C2B C1B C6B C5B -0.1(2) ?
C2B C3B C4B C5B -0.2(2) ?
C4B C5B C6B C1B 0.3(2) ?