#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:05:27 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180286 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/00/7150065.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_7150065
loop_
_publ_author_name
'Sim°unek, Petr'
'Bertolasi, Valerio'
'Pesková, Markéta'
'Machácek, Vladimír'
'Lycka, Antonín'
_publ_section_title
;
 Solution and solid state structure and tautomerism of azo coupled
 enaminone derivatives of benzoylacetone.
;
_journal_issue                   7
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1217
_journal_page_last               1226
_journal_paper_doi               10.1039/b500173k
_journal_volume                  3
_journal_year                    2005
_chemical_formula_moiety         'C17 H17 N3 O'
_chemical_formula_sum            'C17 H17 N3 O'
_chemical_formula_weight         279.34
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 101.110(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7502(1)
_cell_length_b                   29.873(1)
_cell_length_c                   9.1184(3)
_cell_measurement_reflns_used    3370
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.10
_cell_volume                     1536.97(8)
_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    'ORTEP III (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 0.988
_diffrn_measured_fraction_theta_max 0.988
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_sigmaI/netI    0.0987
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16607
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         3.1
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3481
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1437
_refine_ls_R_factor_gt           0.0587
_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)+(0.0476P)²+0.1768P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1347
_reflns_number_gt                1828
_reflns_number_total             3481
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            b500173k.txt
_cod_data_source_block           (III)
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        1536.98(8)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7150065
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
O1 O 0.7677(3) 0.22030(5) -0.22584(17) 0.0443(4) Uani 1 1 d . . .
N1 N 0.5008(3) 0.11873(6) 0.08726(19) 0.0352(5) Uani 1 1 d . . .
H1 H 0.42(3) 0.145(6) 0.135(13) 0.042 Uiso 0.18(5) 1 d P . .
N2 N 0.6414(3) 0.13190(6) 0.00255(19) 0.0346(5) Uani 1 1 d . . .
N3 N 0.3579(3) 0.20216(8) 0.1046(2) 0.0376(5) Uani 1 1 d . . .
H31 H 0.340(6) 0.1709(15) 0.127(3) 0.045 Uiso 0.82(5) 1 d P . .
C1 C 0.6316(4) 0.17608(7) -0.0434(2) 0.0330(5) Uani 1 1 d . . .
C2 C 0.5073(3) 0.21056(7) 0.0132(2) 0.0330(5) Uani 1 1 d . . .
C3 C 0.7770(4) 0.18488(8) -0.1567(2) 0.0357(5) Uani 1 1 d . . .
C4 C 0.5395(4) 0.25874(7) -0.0184(2) 0.0321(5) Uani 1 1 d . . .
C5 C 0.3481(4) 0.28333(8) -0.0922(2) 0.0375(5) Uani 1 1 d . . .
C6 C 0.3746(5) 0.32850(8) -0.1203(3) 0.0454(6) Uani 1 1 d . . .
C7 C 0.5904(5) 0.34899(9) -0.0729(3) 0.0464(7) Uani 1 1 d . . .
C8 C 0.7813(5) 0.32481(8) 0.0039(3) 0.0458(7) Uani 1 1 d . . .
C9 C 0.7559(4) 0.27978(8) 0.0312(3) 0.0396(6) Uani 1 1 d . . .
C10 C 0.9395(5) 0.14828(10) -0.1909(3) 0.0468(7) Uani 1 1 d . . .
C11 C 0.5423(4) 0.07362(7) 0.1371(2) 0.0344(5) Uani 1 1 d . . .
C12 C 0.3899(4) 0.05620(8) 0.2231(3) 0.0464(7) Uani 1 1 d . . .
C13 C 0.4213(5) 0.01334(8) 0.2802(3) 0.0488(7) Uani 1 1 d . . .
C14 C 0.6041(4) -0.01360(8) 0.2540(2) 0.0438(6) Uani 1 1 d . . .
C15 C 0.7540(4) 0.00392(8) 0.1660(3) 0.0496(7) Uani 1 1 d . . .
C16 C 0.7265(4) 0.04671(8) 0.1089(3) 0.0452(6) Uani 1 1 d . . .
C17 C 0.6379(7) -0.06009(10) 0.3160(4) 0.0632(9) Uani 1 1 d . . .
H32 H 0.305(4) 0.2259(8) 0.152(3) 0.053(7) Uiso 1 1 d . . .
H5 H 0.195(4) 0.2677(7) -0.128(2) 0.042(6) Uiso 1 1 d . . .
H6 H 0.236(4) 0.3457(7) -0.172(3) 0.055(7) Uiso 1 1 d . . .
H7 H 0.602(4) 0.3800(8) -0.094(2) 0.044(6) Uiso 1 1 d . . .
H8 H 0.935(4) 0.3390(7) 0.041(2) 0.051(7) Uiso 1 1 d . . .
H9 H 0.883(3) 0.2629(7) 0.081(2) 0.030(6) Uiso 1 1 d . . .
H101 H 0.861(5) 0.1241(10) -0.238(3) 0.089(11) Uiso 1 1 d . . .
H102 H 1.053(4) 0.1611(8) -0.249(3) 0.072(8) Uiso 1 1 d . . .
H103 H 1.045(4) 0.1350(9) -0.102(3) 0.072(9) Uiso 1 1 d . . .
H12 H 0.257(4) 0.0759(7) 0.234(2) 0.050(7) Uiso 1 1 d . . .
H13 H 0.311(4) 0.0001(8) 0.341(3) 0.074(8) Uiso 1 1 d . . .
H15 H 0.888(4) -0.0151(8) 0.146(3) 0.070(8) Uiso 1 1 d . . .
H16 H 0.828(4) 0.0599(7) 0.044(2) 0.054(7) Uiso 1 1 d . . .
H171 H 0.535(5) -0.0657(9) 0.390(3) 0.084(9) Uiso 1 1 d . . .
H172 H 0.611(5) -0.0825(11) 0.248(4) 0.089(11) Uiso 1 1 d . . .
H173 H 0.806(6) -0.0699(11) 0.347(4) 0.115(13) 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 113.24(17) . . ?
N2 N1 H1 114(6) . . ?
C11 N1 H1 129(7) . . ?
N1 N2 C1 118.78(17) . . ?
C2 N3 H31 114.8(19) . . ?
C2 N3 H32 117.9(14) . . ?
H31 N3 H32 126(2) . . ?
N2 C1 C2 125.54(17) . . ?
N2 C1 C3 112.80(17) . . ?
C2 C1 C3 121.60(19) . . ?
N3 C2 C1 121.8(2) . . ?
N3 C2 C4 115.05(18) . . ?
C1 C2 C4 123.12(17) . . ?
O1 C3 C1 122.7(2) . . ?
O1 C3 C10 119.06(19) . . ?
C1 C3 C10 118.3(2) . . ?
C5 C4 C9 119.7(2) . . ?
C5 C4 C2 119.40(19) . . ?
C9 C4 C2 120.8(2) . . ?
C4 C5 C6 120.0(2) . . ?
C4 C5 H5 118.7(12) . . ?
C6 C5 H5 121.2(12) . . ?
C7 C6 C5 119.9(3) . . ?
C7 C6 H6 120.9(13) . . ?
C5 C6 H6 119.1(13) . . ?
C6 C7 C8 120.3(3) . . ?
C6 C7 H7 117.8(14) . . ?
C8 C7 H7 121.9(14) . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 H8 118.5(14) . . ?
C7 C8 H8 121.6(13) . . ?
C8 C9 C4 120.0(3) . . ?
C8 C9 H9 121.0(12) . . ?
C4 C9 H9 118.9(12) . . ?
C3 C10 H101 113.5(18) . . ?
C3 C10 H102 109.0(14) . . ?
H101 C10 H102 112(2) . . ?
C3 C10 H103 115.1(14) . . ?
H101 C10 H103 104(2) . . ?
H102 C10 H103 103(2) . . ?
C12 C11 C16 118.3(2) . . ?
C12 C11 N1 116.70(18) . . ?
C16 C11 N1 124.96(18) . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 H12 124.1(12) . . ?
C11 C12 H12 115.1(12) . . ?
C14 C13 C12 121.6(2) . . ?
C14 C13 H13 116.8(14) . . ?
C12 C13 H13 121.6(14) . . ?
C13 C14 C15 117.3(2) . . ?
C13 C14 C17 121.5(2) . . ?
C15 C14 C17 121.2(2) . . ?
C16 C15 C14 122.0(2) . . ?
C16 C15 H15 119.7(14) . . ?
C14 C15 H15 118.3(14) . . ?
C15 C16 C11 120.1(2) . . ?
C15 C16 H16 123.9(13) . . ?
C11 C16 H16 115.9(13) . . ?
C14 C17 H171 111.2(16) . . ?
C14 C17 H172 116(2) . . ?
H171 C17 H172 107(2) . . ?
C14 C17 H173 115.4(19) . . ?
H171 C17 H173 115(2) . . ?
H172 C17 H173 90(2) . . ?
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 1.228(3) . ?
N1 N2 1.283(2) . ?
N1 C11 1.428(3) . ?
N1 H1 1.07(19) . ?
N2 C1 1.383(3) . ?
N3 C2 1.331(3) . ?
N3 H31 0.96(4) . ?
N3 H32 0.92(2) . ?
C1 C2 1.407(3) . ?
C1 C3 1.472(3) . ?
C2 C4 1.487(3) . ?
C3 C10 1.510(3) . ?
C4 C5 1.385(3) . ?
C4 C9 1.390(3) . ?
C5 C6 1.387(3) . ?
C5 H5 0.99(2) . ?
C6 C7 1.376(3) . ?
C6 H6 0.99(2) . ?
C7 C8 1.386(3) . ?
C7 H7 0.95(2) . ?
C8 C9 1.381(3) . ?
C8 H8 0.98(2) . ?
C9 H9 0.93(2) . ?
C10 H101 0.91(3) . ?
C10 H102 0.99(3) . ?
C10 H103 0.99(3) . ?
C11 C12 1.385(3) . ?
C11 C16 1.392(3) . ?
C12 C13 1.381(3) . ?
C12 H12 0.99(2) . ?
C13 C14 1.381(3) . ?
C13 H13 1.00(2) . ?
C14 C15 1.388(3) . ?
C14 C17 1.498(3) . ?
C15 C16 1.378(3) . ?
C15 H15 1.00(2) . ?
C16 H16 0.99(2) . ?
C17 H171 1.00(3) . ?
C17 H172 0.90(3) . ?
C17 H173 1.00(4) . ?
