#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:21:35 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180074 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/20/7052084.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_7052084
loop_
_publ_author_name
'Petr Šim°unek'
'Markéta Svobodová'
'Valerio Bertolasi'
'Loretta Pretto'
'Antonín Lyčka'
'Vladimír Macháček'
_publ_section_title
;
 Structure and tautomerism of azo coupling products from
 N-alkylenaminones derived from acetylacetone and benzoylacetone in
 solid phase and in solution
;
_journal_issue                   3
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              429
_journal_paper_doi               10.1039/b613346k
_journal_volume                  31
_journal_year                    2007
_chemical_formula_moiety         'C17 H16 N4 O3'
_chemical_formula_sum            'C17 H16 N4 O3'
_chemical_formula_weight         324.34
_chemical_name_systematic
;
?
;
_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'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.2804(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0995(1)
_cell_length_b                   9.5542(2)
_cell_length_c                   20.4491(4)
_cell_measurement_reflns_used    4286
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      2.5
_cell_volume                     1565.94(5)
_computing_cell_refinement       'Denzo SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997)'
_computing_data_reduction        'Denzo SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEPIII (Burnett & Johnson, 1996)'
_computing_publication_material
;
SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'φ scans and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            24759
_diffrn_reflns_theta_full        30.02
_diffrn_reflns_theta_max         30.0
_diffrn_reflns_theta_min         2.5
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4463
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0493
_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)+(0.0570P)²+0.4945P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1316
_reflns_number_gt                3343
_reflns_number_total             4463
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            b613346k.txt
_cod_data_source_block           (6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7052084
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_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
O1 O 0.36632(15) 0.71377(11) 0.19497(5) 0.0432(3) Uani 1 1 d . . .
O2 O -0.19224(15) 0.54000(13) -0.26514(6) 0.0521(3) Uani 1 1 d . . .
O3 O -0.07688(14) 0.34179(15) -0.28298(5) 0.0547(3) Uani 1 1 d . . .
N1 N 0.28400(14) 0.44918(12) 0.00557(5) 0.0291(2) Uani 1 1 d . . .
H1 H 0.316(12) 0.363(11) 0.025(5) 0.035 Uiso 0.17(2) 1 d P . .
N2 N 0.28589(13) 0.56569(11) 0.03821(5) 0.0281(2) Uani 1 1 d . . .
N3 N 0.46014(15) 0.33578(13) 0.10664(6) 0.0327(3) Uani 1 1 d . . .
H3 H 0.400(3) 0.331(2) 0.0662(11) 0.039 Uiso 0.83(2) 1 d P . .
N4 N -0.09684(15) 0.44279(15) -0.24754(6) 0.0404(3) Uani 1 1 d . . .
C1 C 0.37051(16) 0.57240(14) 0.10053(6) 0.0292(3) Uani 1 1 d . . .
C2 C 0.46319(16) 0.45892(14) 0.13515(6) 0.0297(3) Uani 1 1 d . . .
C3 C 0.34579(17) 0.70498(15) 0.13434(6) 0.0317(3) Uani 1 1 d . . .
C4 C 0.56644(19) 0.47505(17) 0.20161(7) 0.0361(3) Uani 1 1 d . . .
C5 C 0.28597(16) 0.83364(14) 0.09544(6) 0.0296(3) Uani 1 1 d . . .
C6 C 0.32844(17) 0.86707(15) 0.03348(7) 0.0317(3) Uani 1 1 d . . .
C7 C 0.27224(18) 0.99098(15) 0.00224(7) 0.0346(3) Uani 1 1 d . . .
C8 C 0.17148(18) 1.08140(16) 0.03187(7) 0.0365(3) Uani 1 1 d . . .
C9 C 0.12954(19) 1.04968(16) 0.09383(7) 0.0374(3) Uani 1 1 d . . .
C10 C 0.18819(18) 0.92759(15) 0.12546(7) 0.0345(3) Uani 1 1 d . . .
C11 C 0.18656(15) 0.45626(14) -0.05750(6) 0.0279(3) Uani 1 1 d . . .
C12 C 0.19516(17) 0.33997(15) -0.09826(6) 0.0309(3) Uani 1 1 d . . .
C13 C 0.10174(17) 0.33472(15) -0.16076(7) 0.0330(3) Uani 1 1 d . . .
C14 C -0.00017(16) 0.44729(15) -0.18121(6) 0.0328(3) Uani 1 1 d . . .
C15 C -0.01181(17) 0.56386(16) -0.14195(7) 0.0338(3) Uani 1 1 d . . .
C16 C 0.08220(17) 0.56885(15) -0.07983(7) 0.0318(3) Uani 1 1 d . . .
C17 C 0.5464(2) 0.21061(17) 0.13494(8) 0.0382(3) Uani 1 1 d . . .
H41 H 0.599(2) 0.5732(19) 0.2099(8) 0.039(4) Uiso 1 1 d . . .
H42 H 0.501(2) 0.4441(19) 0.2372(9) 0.051(5) Uiso 1 1 d . . .
H43 H 0.667(2) 0.416(2) 0.2044(9) 0.049(5) Uiso 1 1 d . . .
H6 H 0.397(2) 0.8037(18) 0.0124(8) 0.040(4) Uiso 1 1 d . . .
H7 H 0.303(2) 1.0128(18) -0.0411(9) 0.046(5) Uiso 1 1 d . . .
H8 H 0.129(2) 1.1662(18) 0.0091(8) 0.040(4) Uiso 1 1 d . . .
H9 H 0.060(2) 1.113(2) 0.1152(8) 0.047(5) Uiso 1 1 d . . .
H10 H 0.160(2) 0.9040(17) 0.1686(8) 0.037(4) Uiso 1 1 d . . .
H12 H 0.109(2) 0.2525(19) -0.1891(8) 0.043(4) Uiso 1 1 d . . .
H13 H 0.268(2) 0.2633(18) -0.0838(8) 0.037(4) Uiso 1 1 d . . .
H15 H -0.086(2) 0.6393(19) -0.1575(8) 0.040(4) Uiso 1 1 d . . .
H16 H 0.0780(19) 0.6492(18) -0.0511(8) 0.037(4) Uiso 1 1 d . . .
H171 H 0.500(2) 0.1285(19) 0.1103(8) 0.042(4) Uiso 1 1 d . . .
H172 H 0.530(2) 0.197(2) 0.1808(10) 0.062(6) Uiso 1 1 d . . .
H173 H 0.665(3) 0.216(2) 0.1320(9) 0.055(5) Uiso 1 1 d . . .
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
N2 N1 C11 113.10(11) . . ?
N2 N1 H1 124(6) . . ?
C11 N1 H1 121(6) . . ?
N1 N2 C1 119.36(11) . . ?
C2 N3 C17 125.48(12) . . ?
C2 N3 H3 115.5(13) . . ?
C17 N3 H3 119.0(13) . . ?
O2 N4 O3 123.39(13) . . ?
O2 N4 C14 118.59(13) . . ?
O3 N4 C14 118.02(13) . . ?
N2 C1 C2 125.49(12) . . ?
N2 C1 C3 113.40(11) . . ?
C2 C1 C3 120.82(11) . . ?
N3 C2 C1 118.69(12) . . ?
N3 C2 C4 117.91(12) . . ?
C1 C2 C4 123.39(12) . . ?
O1 C3 C1 121.67(12) . . ?
O1 C3 C5 117.60(12) . . ?
C1 C3 C5 120.66(11) . . ?
C2 C4 H41 110.9(10) . . ?
C2 C4 H42 110.1(10) . . ?
H41 C4 H42 108.3(14) . . ?
C2 C4 H43 110.0(10) . . ?
H41 C4 H43 109.5(15) . . ?
H42 C4 H43 108.0(15) . . ?
C10 C5 C6 118.76(13) . . ?
C10 C5 C3 116.88(12) . . ?
C6 C5 C3 124.28(12) . . ?
C7 C6 C5 120.29(13) . . ?
C7 C6 H6 120.0(10) . . ?
C5 C6 H6 119.7(10) . . ?
C8 C7 C6 120.28(13) . . ?
C8 C7 H7 120.3(10) . . ?
C6 C7 H7 119.4(10) . . ?
C7 C8 C9 119.90(14) . . ?
C7 C8 H8 120.0(10) . . ?
C9 C8 H8 120.1(10) . . ?
C10 C9 C8 119.77(14) . . ?
C10 C9 H9 119.9(10) . . ?
C8 C9 H9 120.4(10) . . ?
C9 C10 C5 120.96(13) . . ?
C9 C10 H10 120.9(10) . . ?
C5 C10 H10 118.2(10) . . ?
C12 C11 C16 119.69(12) . . ?
C12 C11 N1 115.92(12) . . ?
C16 C11 N1 124.37(12) . . ?
C13 C12 C11 120.68(13) . . ?
C13 C12 H13 119.1(9) . . ?
C11 C12 H13 120.2(9) . . ?
C14 C13 C12 118.19(13) . . ?
C14 C13 H12 121.8(10) . . ?
C12 C13 H12 120.0(10) . . ?
C13 C14 C15 122.53(12) . . ?
C13 C14 N4 118.22(13) . . ?
C15 C14 N4 119.24(13) . . ?
C14 C15 C16 119.05(13) . . ?
C14 C15 H15 120.2(10) . . ?
C16 C15 H15 120.8(10) . . ?
C15 C16 C11 119.86(13) . . ?
C15 C16 H16 121.4(9) . . ?
C11 C16 H16 118.7(9) . . ?
N3 C17 H171 109.0(10) . . ?
N3 C17 H172 111.4(12) . . ?
H171 C17 H172 107.0(16) . . ?
N3 C17 H173 110.6(11) . . ?
H171 C17 H173 108.8(15) . . ?
H172 C17 H173 109.9(16) . . ?
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
O1 C3 1.2298(16) . ?
O2 N4 1.2285(18) . ?
O3 N4 1.2314(18) . ?
N1 N2 1.2969(15) . ?
N1 C11 1.4134(16) . ?
N1 H1 0.93(11) . ?
N2 C1 1.3587(16) . ?
N3 C2 1.3117(18) . ?
N3 C17 1.4619(18) . ?
N3 H3 0.90(2) . ?
N4 C14 1.4659(17) . ?
C1 C2 1.4448(19) . ?
C1 C3 1.4705(19) . ?
C2 C4 1.4975(19) . ?
C3 C5 1.5059(19) . ?
C4 H41 0.983(18) . ?
C4 H42 1.003(19) . ?
C4 H43 0.982(19) . ?
C5 C10 1.3964(19) . ?
C5 C6 1.3968(18) . ?
C6 C7 1.390(2) . ?
C6 H6 0.967(17) . ?
C7 C8 1.386(2) . ?
C7 H7 0.976(17) . ?
C8 C9 1.392(2) . ?
C8 H8 0.973(17) . ?
C9 C10 1.384(2) . ?
C9 H9 0.977(18) . ?
C10 H10 0.969(16) . ?
C11 C12 1.3966(18) . ?
C11 C16 1.4032(19) . ?
C12 C13 1.3893(18) . ?
C12 H13 0.962(17) . ?
C13 C14 1.383(2) . ?
C13 H12 0.983(18) . ?
C14 C15 1.384(2) . ?
C15 C16 1.3846(19) . ?
C15 H15 0.961(18) . ?
C16 H16 0.970(17) . ?
C17 H171 0.978(18) . ?
C17 H172 0.97(2) . ?
C17 H173 0.97(2) . ?
