#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/34/7203439.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_7203439
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         'C21 H19 N 04'
_chemical_formula_sum            'C21 H19 N O4'
_chemical_formula_weight         349.37
_chemical_name_common
;(E,E)-2-(4-Methoxybenzylidene)-6-(4-
nitrobenzylidene)cyclohexanone
;
_chemical_name_systematic
;
(E,E)-2-(4-Methoxybenzylidene)-6-(4-nitrobenzylidene)cyclohexanone
;
_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                95.5870(10)
_cell_angle_beta                 102.8010(10)
_cell_angle_gamma                91.992(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8646(3)
_cell_length_b                   9.6830(3)
_cell_length_c                   11.3746(5)
_cell_measurement_temperature    123(2)
_cell_volume                     839.25(6)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω 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  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0546
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6955
_diffrn_reflns_theta_full        25.66
_diffrn_reflns_theta_max         25.66
_diffrn_reflns_theta_min         3.54
_exptl_absorpt_coefficient_mu    0.096
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3102
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0400
_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)+(0.0510P)²+0.0562P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.1018
_reflns_number_gt                2280
_reflns_number_total             3102
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b606042k.cif.txt
_cod_data_source_block           1o
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7203439
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
O2 O 1.09975(15) -0.10826(11) 0.91272(10) 0.0240(3) Uani 1 1 d . . .
C22 C -0.0103(2) 0.65761(16) 0.10201(15) 0.0195(4) Uani 1 1 d . . .
H22 H -0.0039 0.7371 0.0600 0.023 Uiso 1 1 calc R . .
C18 C 0.1315(2) 0.47759(16) 0.21632(14) 0.0181(4) Uani 1 1 d . . .
C21 C -0.1839(2) 0.48448(16) 0.17268(14) 0.0198(4) Uani 1 1 d . . .
H21 H -0.2950 0.4474 0.1780 0.024 Uiso 1 1 calc R . .
C19 C -0.0335(2) 0.42268(16) 0.22288(14) 0.0192(4) Uani 1 1 d . . .
H19 H -0.0415 0.3416 0.2626 0.023 Uiso 1 1 calc R . .
C5 C 0.8341(2) -0.04018(16) 0.80382(14) 0.0204(4) Uani 1 1 d . . .
H5 H 0.7789 -0.0833 0.8582 0.024 Uiso 1 1 calc R . .
C11 C 0.4402(2) 0.21769(16) 0.59702(15) 0.0200(4) Uani 1 1 d . . .
H11A H 0.5102 0.2261 0.6815 0.024 Uiso 1 1 calc R . .
H11B H 0.3715 0.1275 0.5815 0.024 Uiso 1 1 calc R . .
C23 C -0.1694(2) 0.60182(16) 0.11426(14) 0.0186(4) Uani 1 1 d . . .
C3 C 1.0145(2) -0.04321(15) 0.81798(14) 0.0200(4) Uani 1 1 d . . .
C13 C 0.2121(2) 0.33023(16) 0.45321(15) 0.0209(4) Uani 1 1 d . . .
H13A H 0.1430 0.2405 0.4296 0.025 Uiso 1 1 calc R . .
H13B H 0.1297 0.4056 0.4470 0.025 Uiso 1 1 calc R . .
C7 C 0.7348(2) 0.02474(16) 0.71176(15) 0.0205(4) Uani 1 1 d . . .
H7 H 0.6119 0.0253 0.7036 0.025 Uiso 1 1 calc R . .
C15 C 0.5084(2) 0.28763(16) 0.39731(15) 0.0197(4) Uani 1 1 d . . .
C14 C 0.3315(2) 0.34692(16) 0.36755(15) 0.0191(4) Uani 1 1 d . . .
C4 C 1.0942(2) 0.01675(16) 0.73609(15) 0.0223(4) Uani 1 1 d . . .
H4 H 1.2167 0.0137 0.7435 0.027 Uiso 1 1 calc R . .
C6 C 0.9923(2) 0.08120(16) 0.64337(15) 0.0214(4) Uani 1 1 d . . .
H6 H 1.0476 0.1206 0.5872 0.026 Uiso 1 1 calc R . .
C10 C 0.5621(2) 0.21899(16) 0.51126(14) 0.0188(4) Uani 1 1 d . . .
C8 C 0.8122(2) 0.09054(16) 0.62922(14) 0.0187(4) Uani 1 1 d . . .
C12 C 0.3156(2) 0.33470(16) 0.58345(15) 0.0216(4) Uani 1 1 d . . .
H12A H 0.2342 0.3260 0.6377 0.026 Uiso 1 1 calc R . .
H12B H 0.3828 0.4252 0.6078 0.026 Uiso 1 1 calc R . .
C20 C 0.1386(2) 0.59378(16) 0.15292(14) 0.0200(4) Uani 1 1 d . . .
H20 H 0.2489 0.6297 0.1447 0.024 Uiso 1 1 calc R . .
O25 O -0.32143(16) 0.76067(13) -0.00272(12) 0.0342(3) Uani 1 1 d . . .
O16 O 0.60686(15) 0.29419(12) 0.32714(11) 0.0291(3) Uani 1 1 d . . .
N24 N -0.32882(18) 0.67007(14) 0.06475(12) 0.0229(3) Uani 1 1 d . . .
C17 C 0.2941(2) 0.41461(16) 0.26801(15) 0.0192(4) Uani 1 1 d . . .
H17 H 0.3849 0.4226 0.2258 0.023 Uiso 1 1 calc R . .
O26 O -0.46432(16) 0.63478(14) 0.09346(13) 0.0420(4) Uani 1 1 d . . .
C9 C 0.7205(2) 0.16457(15) 0.53094(15) 0.0190(4) Uani 1 1 d . . .
H9 H 0.7831 0.1768 0.4699 0.023 Uiso 1 1 calc R . .
C1 C 1.2849(2) -0.11740(18) 0.92877(16) 0.0269(4) Uani 1 1 d . . .
H1A H 1.3103 -0.1671 0.8560 0.040 Uiso 1 1 calc R . .
H1B H 1.3294 -0.1677 0.9989 0.040 Uiso 1 1 calc R . .
H1C H 1.3415 -0.0236 0.9424 0.040 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
C3 O2 C1 117.76(12) . . ?
C20 C22 C23 117.78(15) . . ?
C20 C18 C19 118.11(15) . . ?
C20 C18 C17 119.09(14) . . ?
C19 C18 C17 122.73(14) . . ?
C19 C21 C23 118.51(15) . . ?
C21 C19 C18 121.10(14) . . ?
C7 C5 C3 120.74(14) . . ?
C10 C11 C12 112.59(13) . . ?
C21 C23 C22 122.67(16) . . ?
C21 C23 N24 118.38(14) . . ?
C22 C23 N24 118.95(14) . . ?
O2 C3 C4 124.76(15) . . ?
O2 C3 C5 115.80(14) . . ?
C4 C3 C5 119.44(15) . . ?
C14 C13 C12 111.17(14) . . ?
C5 C7 C8 121.31(15) . . ?
O16 C15 C10 120.59(15) . . ?
O16 C15 C14 119.86(14) . . ?
C10 C15 C14 119.55(14) . . ?
C17 C14 C15 117.06(14) . . ?
C17 C14 C13 124.98(15) . . ?
C15 C14 C13 117.94(14) . . ?
C6 C4 C3 119.15(16) . . ?
C4 C6 C8 122.87(15) . . ?
C9 C10 C15 116.57(14) . . ?
C9 C10 C11 124.53(15) . . ?
C15 C10 C11 118.88(14) . . ?
C6 C8 C7 116.41(15) . . ?
C6 C8 C9 117.78(14) . . ?
C7 C8 C9 125.80(15) . . ?
C13 C12 C11 110.82(14) . . ?
C22 C20 C18 121.76(15) . . ?
O25 N24 O26 122.81(14) . . ?
O25 N24 C23 118.83(13) . . ?
O26 N24 C23 118.35(13) . . ?
C14 C17 C18 128.38(15) . . ?
C10 C9 C8 131.35(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
O2 C3 1.3597(19) . ?
O2 C1 1.434(2) . ?
C22 C20 1.382(2) . ?
C22 C23 1.386(2) . ?
C18 C20 1.400(2) . ?
C18 C19 1.405(2) . ?
C18 C17 1.464(2) . ?
C21 C19 1.378(2) . ?
C21 C23 1.385(2) . ?
C5 C7 1.379(2) . ?
C5 C3 1.394(2) . ?
C11 C10 1.513(2) . ?
C11 C12 1.521(2) . ?
C23 N24 1.464(2) . ?
C3 C4 1.391(2) . ?
C13 C14 1.511(2) . ?
C13 C12 1.520(2) . ?
C7 C8 1.414(2) . ?
C15 O16 1.2332(19) . ?
C15 C10 1.498(2) . ?
C15 C14 1.505(2) . ?
C14 C17 1.345(2) . ?
C4 C6 1.390(2) . ?
C6 C8 1.397(2) . ?
C10 C9 1.351(2) . ?
C8 C9 1.455(2) . ?
O25 N24 1.2285(16) . ?
N24 O26 1.2286(18) . ?
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
C23 C21 C19 C18 0.6(2) . . . . ?
C20 C18 C19 C21 -2.6(2) . . . . ?
C17 C18 C19 C21 -179.71(15) . . . . ?
C19 C21 C23 C22 1.4(2) . . . . ?
C19 C21 C23 N24 -177.89(14) . . . . ?
C20 C22 C23 C21 -1.4(2) . . . . ?
C20 C22 C23 N24 177.97(14) . . . . ?
C1 O2 C3 C4 -0.8(2) . . . . ?
C1 O2 C3 C5 178.26(14) . . . . ?
C7 C5 C3 O2 179.11(14) . . . . ?
C7 C5 C3 C4 -1.8(2) . . . . ?
C3 C5 C7 C8 -0.2(2) . . . . ?
O16 C15 C14 C17 -4.8(2) . . . . ?
C10 C15 C14 C17 176.14(14) . . . . ?
O16 C15 C14 C13 177.08(15) . . . . ?
C10 C15 C14 C13 -1.9(2) . . . . ?
C12 C13 C14 C17 -144.57(16) . . . . ?
C12 C13 C14 C15 33.34(19) . . . . ?
O2 C3 C4 C6 -179.54(14) . . . . ?
C5 C3 C4 C6 1.4(2) . . . . ?
C3 C4 C6 C8 0.9(3) . . . . ?
O16 C15 C10 C9 -0.8(2) . . . . ?
C14 C15 C10 C9 178.23(14) . . . . ?
O16 C15 C10 C11 177.85(15) . . . . ?
C14 C15 C10 C11 -3.1(2) . . . . ?
C12 C11 C10 C9 154.80(15) . . . . ?
C12 C11 C10 C15 -23.7(2) . . . . ?
C4 C6 C8 C7 -2.8(2) . . . . ?
C4 C6 C8 C9 178.02(15) . . . . ?
C5 C7 C8 C6 2.4(2) . . . . ?
C5 C7 C8 C9 -178.48(15) . . . . ?
C14 C13 C12 C11 -60.60(17) . . . . ?
C10 C11 C12 C13 55.77(17) . . . . ?
C23 C22 C20 C18 -0.8(2) . . . . ?
C19 C18 C20 C22 2.7(2) . . . . ?
C17 C18 C20 C22 179.92(15) . . . . ?
C21 C23 N24 O25 -169.07(15) . . . . ?
C22 C23 N24 O25 11.6(2) . . . . ?
C21 C23 N24 O26 11.5(2) . . . . ?
C22 C23 N24 O26 -167.85(16) . . . . ?
C15 C14 C17 C18 177.73(15) . . . . ?
C13 C14 C17 C18 -4.3(3) . . . . ?
C20 C18 C17 C14 149.93(17) . . . . ?
C19 C18 C17 C14 -33.0(3) . . . . ?
C15 C10 C9 C8 -179.22(15) . . . . ?
C11 C10 C9 C8 2.2(3) . . . . ?
C6 C8 C9 C10 -162.11(17) . . . . ?
C7 C8 C9 C10 18.8(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9705165
