#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:57:42 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180365 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/34/7203442.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_7203442
loop_
_publ_author_name
'Rosamilia, Anthony E.'
'Giarrusso, Marilena A.'
'Scott, Janet L.'
'Strauss, Christopher R.'
_publ_section_title
;
 A direct, efficient synthesis of unsymmetrically substituted
 bis(arylidene)alkanones
;
_journal_issue                   12
_journal_name_full               'Green Chemistry'
_journal_page_first              1042
_journal_paper_doi               10.1039/b606042k
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C26 H31 N3 O'
_chemical_formula_sum            'C26 H31 N3 O'
_chemical_formula_weight         401.54
_chemical_name_systematic
;
(E)-N,N-dimethyl-9-(pyridin-4-yl)-5-(pyridin-4-ylmethylene)
-2,3,4,4a,5,6,7,8,9,9a-decahydro-1H-xanthen-4a-amine
;
_space_group_IT_number           14
_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                 103.9810(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.08960(10)
_cell_length_b                   13.2900(2)
_cell_length_c                   16.6649(3)
_cell_measurement_temperature    123(2)
_cell_volume                     2168.41(6)
_computing_cell_refinement       'Nonius collect'
_computing_data_collection       'Nonius collect'
_computing_data_reduction        'Nonius collect'
_computing_molecular_graphics    X-Seed
_computing_publication_material  ciftab
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'phi and omega scans'
_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  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0436
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            30375
_diffrn_reflns_theta_full        28.19
_diffrn_reflns_theta_max         28.19
_diffrn_reflns_theta_min         3.71
_exptl_absorpt_coefficient_mu    0.076
_exptl_crystal_colour            block
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       colourless
_exptl_crystal_F_000             864
_exptl_crystal_size_max          .45
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .3
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5297
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0498
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0425P)²+0.7951P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1113
_reflns_number_gt                3772
_reflns_number_total             5297
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b606042k.cif.txt
_cod_data_source_block           8b
_cod_database_code               7203442
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
O10 O 0.79851(10) 0.94087(7) 0.07655(6) 0.0200(2) Uani 1 1 d . . .
N1 N 0.92494(11) 0.86695(9) 0.19829(7) 0.0201(3) Uani 1 1 d . . .
C9A C 0.88833(13) 0.77121(10) 0.06742(8) 0.0161(3) Uani 1 1 d . . .
H9A H 0.9759 0.8002 0.0598 0.019 Uiso 1 1 calc R . .
C1 C 0.92004(14) 0.66968(10) 0.11179(8) 0.0205(3) Uani 1 1 d . . .
H1A H 0.9557 0.6226 0.0760 0.025 Uiso 1 1 calc R . .
H1B H 0.9920 0.6793 0.1634 0.025 Uiso 1 1 calc R . .
C4A C 0.82840(13) 0.84453(10) 0.12047(8) 0.0170(3) Uani 1 1 d . . .
C8A C 0.72015(13) 0.85448(10) -0.05231(8) 0.0179(3) Uani 1 1 d . . .
C5 C 0.68567(13) 1.03762(11) -0.04013(8) 0.0187(3) Uani 1 1 d . . .
C5A C 0.73294(13) 0.93821(10) -0.00598(8) 0.0175(3) Uani 1 1 d . . .
C4 C 0.69751(14) 0.79950(11) 0.13612(9) 0.0207(3) Uani 1 1 d . . .
H4A H 0.6296 0.7905 0.0827 0.025 Uiso 1 1 calc R . .
H4B H 0.6585 0.8464 0.1704 0.025 Uiso 1 1 calc R . .
C9 C 0.79018(14) 0.75778(10) -0.01914(8) 0.0173(3) Uani 1 1 d . . .
H9 H 0.7184 0.7079 -0.0141 0.021 Uiso 1 1 calc R . .
C7 C 0.53530(14) 0.94154(11) -0.15574(8) 0.0217(3) Uani 1 1 d . . .
H7A H 0.4656 0.9346 -0.1233 0.026 Uiso 1 1 calc R . .
H7B H 0.4879 0.9441 -0.2151 0.026 Uiso 1 1 calc R . .
C12 C 0.70641(14) 1.12004(10) 0.00789(9) 0.0203(3) Uani 1 1 d . . .
H12 H 0.7460 1.1094 0.0650 0.024 Uiso 1 1 calc R . .
C6 C 0.61662(14) 1.03784(11) -0.13112(8) 0.0204(3) Uani 1 1 d . . .
H6A H 0.6864 1.0442 -0.1636 0.024 Uiso 1 1 calc R . .
H6B H 0.5547 1.0965 -0.1440 0.024 Uiso 1 1 calc R . .
N1" N 0.61472(14) 1.42951(10) -0.06116(8) 0.0308(3) Uani 1 1 d . . .
C4' C 0.86952(14) 0.71511(10) -0.07798(8) 0.0188(3) Uani 1 1 d . . .
C3' C 0.85499(15) 0.61551(11) -0.10394(8) 0.0236(3) Uani 1 1 d . . .
H3' H 0.7930 0.5722 -0.0860 0.028 Uiso 1 1 calc R . .
C8 C 0.63159(14) 0.85235(11) -0.13953(8) 0.0218(3) Uani 1 1 d . . .
H8A H 0.5779 0.7892 -0.1482 0.026 Uiso 1 1 calc R . .
H8B H 0.6904 0.8534 -0.1792 0.026 Uiso 1 1 calc R . .
N1' N 1.02138(14) 0.63541(11) -0.18509(8) 0.0320(3) Uani 1 1 d . . .
C3 C 0.72573(15) 0.69768(11) 0.18029(9) 0.0240(3) Uani 1 1 d . . .
H3A H 0.7856 0.7081 0.2362 0.029 Uiso 1 1 calc R . .
H3B H 0.6385 0.6687 0.1868 0.029 Uiso 1 1 calc R . .
C2' C 0.93228(17) 0.58016(12) -0.15652(9) 0.0298(4) Uani 1 1 d . . .
H2' H 0.9210 0.5118 -0.1734 0.036 Uiso 1 1 calc R . .
C2 C 0.79383(15) 0.62360(11) 0.13281(9) 0.0232(3) Uani 1 1 d . . .
H2A H 0.7277 0.6036 0.0811 0.028 Uiso 1 1 calc R . .
H2B H 0.8207 0.5623 0.1666 0.028 Uiso 1 1 calc R . .
C3" C 0.68563(15) 1.26471(11) -0.09372(10) 0.0268(3) Uani 1 1 d . . .
H3" H 0.7137 1.2229 -0.1328 0.032 Uiso 1 1 calc R . .
C6' C 1.03388(16) 0.73129(13) -0.15967(9) 0.0303(4) Uani 1 1 d . . .
H6' H 1.0964 0.7729 -0.1788 0.036 Uiso 1 1 calc R . .
C4" C 0.67467(14) 1.22510(11) -0.01810(9) 0.0207(3) Uani 1 1 d . . .
C5' C 0.96181(15) 0.77388(12) -0.10742(9) 0.0253(3) Uani 1 1 d . . .
H5' H 0.9752 0.8426 -0.0918 0.030 Uiso 1 1 calc R . .
C5" C 0.63421(15) 1.29258(11) 0.03540(9) 0.0249(3) Uani 1 1 d . . .
H5" H 0.6267 1.2706 0.0884 0.030 Uiso 1 1 calc R . .
C1N C 1.05603(15) 0.90623(13) 0.18997(10) 0.0302(4) Uani 1 1 d . . .
H1N1 H 1.0981 0.8580 0.1591 0.045 Uiso 1 1 calc R . .
H1N2 H 1.1163 0.9166 0.2450 0.045 Uiso 1 1 calc R . .
H1N3 H 1.0417 0.9704 0.1602 0.045 Uiso 1 1 calc R . .
C6" C 0.60484(16) 1.39165(12) 0.01162(10) 0.0285(3) Uani 1 1 d . . .
H6" H 0.5760 1.4353 0.0492 0.034 Uiso 1 1 calc R . .
C2N C 0.87104(16) 0.93231(12) 0.25392(9) 0.0295(4) Uani 1 1 d . . .
H2N1 H 0.8409 0.9962 0.2261 0.044 Uiso 1 1 calc R . .
H2N2 H 0.9427 0.9452 0.3041 0.044 Uiso 1 1 calc R . .
H2N3 H 0.7935 0.8992 0.2687 0.044 Uiso 1 1 calc R . .
C2" C 0.65564(17) 1.36500(12) -0.11169(11) 0.0316(4) Uani 1 1 d . . .
H2" H 0.6648 1.3897 -0.1636 0.038 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5A O10 C4A 117.84(10) . . ?
C4A N1 C1N 114.60(11) . . ?
C4A N1 C2N 114.49(11) . . ?
C1N N1 C2N 109.32(12) . . ?
C4A C9A C1 110.24(11) . . ?
C4A C9A C9 110.93(10) . . ?
C1 C9A C9 111.04(11) . . ?
C2 C1 C9A 111.99(11) . . ?
N1 C4A O10 106.19(10) . . ?
N1 C4A C4 110.41(11) . . ?
O10 C4A C4 110.14(10) . . ?
N1 C4A C9A 111.85(11) . . ?
O10 C4A C9A 109.17(10) . . ?
C4 C4A C9A 109.06(11) . . ?
C5A C8A C9 121.66(12) . . ?
C5A C8A C8 121.39(12) . . ?
C9 C8A C8 116.94(11) . . ?
C12 C5 C5A 120.84(12) . . ?
C12 C5 C6 124.42(13) . . ?
C5A C5 C6 114.74(12) . . ?
C8A C5A O10 123.54(12) . . ?
C8A C5A C5 122.99(12) . . ?
O10 C5A C5 113.35(11) . . ?
C4A C4 C3 111.06(11) . . ?
C8A C9 C4' 110.83(11) . . ?
C8A C9 C9A 112.39(11) . . ?
C4' C9 C9A 109.04(11) . . ?
C8 C7 C6 109.21(11) . . ?
C5 C12 C4" 127.31(13) . . ?
C5 C6 C7 110.94(11) . . ?
C2" N1" C6" 115.60(13) . . ?
C3' C4' C5' 117.00(13) . . ?
C3' C4' C9 121.65(13) . . ?
C5' C4' C9 121.34(12) . . ?
C2' C3' C4' 119.07(14) . . ?
C8A C8 C7 111.19(11) . . ?
C2' N1' C6' 115.52(13) . . ?
C2 C3 C4 112.01(11) . . ?
N1' C2' C3' 124.65(15) . . ?
C3 C2 C1 111.39(12) . . ?
C2" C3" C4" 119.89(14) . . ?
N1' C6' C5' 124.40(15) . . ?
C5" C4" C3" 115.76(13) . . ?
C5" C4" C12 119.88(13) . . ?
C3" C4" C12 124.33(13) . . ?
C6' C5' C4' 119.36(14) . . ?
C6" C5" C4" 120.25(14) . . ?
N1" C6" C5" 123.94(14) . . ?
N1" C2" C3" 124.54(15) . . ?
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
O10 C5A 1.3750(15) . ?
O10 C4A 1.4696(16) . ?
N1 C4A 1.4522(17) . ?
N1 C1N 1.4593(19) . ?
N1 C2N 1.4675(18) . ?
C9A C4A 1.5346(18) . ?
C9A C1 1.5348(18) . ?
C9A C9 1.5501(18) . ?
C1 C2 1.528(2) . ?
C4A C4 1.5287(19) . ?
C8A C5A 1.3427(19) . ?
C8A C9 1.5060(18) . ?
C8A C8 1.5114(19) . ?
C5 C12 1.343(2) . ?
C5 C5A 1.4715(19) . ?
C5 C6 1.5081(19) . ?
C4 C3 1.534(2) . ?
C9 C4' 1.5177(18) . ?
C7 C8 1.515(2) . ?
C7 C6 1.522(2) . ?
C12 C4" 1.4740(19) . ?
N1" C2" 1.335(2) . ?
N1" C6" 1.339(2) . ?
C4' C3' 1.389(2) . ?
C4' C5' 1.392(2) . ?
C3' C2' 1.388(2) . ?
N1' C2' 1.335(2) . ?
N1' C6' 1.339(2) . ?
C3 C2 1.527(2) . ?
C3" C2" 1.383(2) . ?
C3" C4" 1.395(2) . ?
C6' C5' 1.383(2) . ?
C4" C5" 1.393(2) . ?
C5" C6" 1.386(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4A C9A C1 C2 57.04(14) . . . . ?
C9 C9A C1 C2 -66.31(14) . . . . ?
C1N N1 C4A O10 -63.22(14) . . . . ?
C2N N1 C4A O10 64.27(14) . . . . ?
C1N N1 C4A C4 177.41(12) . . . . ?
C2N N1 C4A C4 -55.11(15) . . . . ?
C1N N1 C4A C9A 55.77(15) . . . . ?
C2N N1 C4A C9A -176.75(12) . . . . ?
C5A O10 C4A N1 166.31(10) . . . . ?
C5A O10 C4A C4 -74.14(14) . . . . ?
C5A O10 C4A C9A 45.58(14) . . . . ?
C1 C9A C4A N1 63.00(14) . . . . ?
C9 C9A C4A N1 -173.59(11) . . . . ?
C1 C9A C4A O10 -179.79(10) . . . . ?
C9 C9A C4A O10 -56.38(13) . . . . ?
C1 C9A C4A C4 -59.41(14) . . . . ?
C9 C9A C4A C4 64.00(14) . . . . ?
C9 C8A C5A O10 -6.5(2) . . . . ?
C8 C8A C5A O10 171.88(12) . . . . ?
C9 C8A C5A C5 169.43(12) . . . . ?
C8 C8A C5A C5 -12.2(2) . . . . ?
C4A O10 C5A C8A -14.29(18) . . . . ?
C4A O10 C5A C5 169.44(11) . . . . ?
C12 C5 C5A C8A -176.87(13) . . . . ?
C6 C5 C5A C8A 2.14(19) . . . . ?
C12 C5 C5A O10 -0.58(18) . . . . ?
C6 C5 C5A O10 178.43(11) . . . . ?
N1 C4A C4 C3 -64.28(14) . . . . ?
O10 C4A C4 C3 178.77(10) . . . . ?
C9A C4A C4 C3 58.99(14) . . . . ?
C5A C8A C9 C4' -129.14(14) . . . . ?
C8 C8A C9 C4' 52.44(15) . . . . ?
C5A C8A C9 C9A -6.84(18) . . . . ?
C8 C8A C9 C9A 174.73(11) . . . . ?
C4A C9A C9 C8A 37.88(15) . . . . ?
C1 C9A C9 C8A 160.83(11) . . . . ?
C4A C9A C9 C4' 161.17(11) . . . . ?
C1 C9A C9 C4' -75.87(13) . . . . ?
C5A C5 C12 C4" 175.12(13) . . . . ?
C6 C5 C12 C4" -3.8(2) . . . . ?
C12 C5 C6 C7 -146.27(14) . . . . ?
C5A C5 C6 C7 34.76(16) . . . . ?
C8 C7 C6 C5 -61.64(15) . . . . ?
C8A C9 C4' C3' -129.62(13) . . . . ?
C9A C9 C4' C3' 106.16(14) . . . . ?
C8A C9 C4' C5' 51.35(17) . . . . ?
C9A C9 C4' C5' -72.87(16) . . . . ?
C5' C4' C3' C2' 0.4(2) . . . . ?
C9 C4' C3' C2' -178.72(13) . . . . ?
C5A C8A C8 C7 -15.82(19) . . . . ?
C9 C8A C8 C7 162.61(12) . . . . ?
C6 C7 C8 C8A 51.44(15) . . . . ?
C4A C4 C3 C2 -55.80(15) . . . . ?
C6' N1' C2' C3' 0.0(2) . . . . ?
C4' C3' C2' N1' -0.2(2) . . . . ?
C4 C3 C2 C1 51.96(16) . . . . ?
C9A C1 C2 C3 -52.85(15) . . . . ?
C2' N1' C6' C5' 0.0(2) . . . . ?
C2" C3" C4" C5" -0.6(2) . . . . ?
C2" C3" C4" C12 -178.86(14) . . . . ?
C5 C12 C4" C5" 146.76(15) . . . . ?
C5 C12 C4" C3" -35.1(2) . . . . ?
N1' C6' C5' C4' 0.2(2) . . . . ?
C3' C4' C5' C6' -0.3(2) . . . . ?
C9 C4' C5' C6' 178.73(13) . . . . ?
C3" C4" C5" C6" 1.4(2) . . . . ?
C12 C4" C5" C6" 179.67(13) . . . . ?
C2" N1" C6" C5" 0.0(2) . . . . ?
C4" C5" C6" N1" -1.1(2) . . . . ?
C6" N1" C2" C3" 0.7(2) . . . . ?
C4" C3" C2" N1" -0.4(3) . . . . ?
