#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/52/2015257.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_2015257
loop_
_publ_author_name
'Özek, Arzu'
'Albayrak, Çiǧdem'
'Odabaşoǧlu, Mustafa'
'Büyükgüngör, Orhan'
_publ_section_title
;(Z)-4-(2,6-Dichlorophenyldiazenyl)-6-{[1,3-dihydroxy-2-(hydroxymethyl)propan-2-ylamino]methylene}-2-methoxycyclohexa-2,4-dienone
 and the 3-methoxyphenyldiazenyl and 4-methoxyphenyldiazenyl analogues
;
_journal_coeditor_code           HJ1088
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o173
_journal_page_last               o177
_journal_paper_doi               10.1107/S0108270106005026
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C18 H19 Cl2 N3 O5'
_chemical_formula_moiety         'C18 H19 Cl2 N3 O5'
_chemical_formula_sum            'C18 H19 Cl2 N3 O5'
_chemical_formula_weight         428.26
_chemical_name_systematic
;
(Z)-4-(2,6-dichlorophenyldiazenyl)-6-{[1,3-dihydroxy-2-(hydroxymethyl)propan-
2-ylamino]methylene}-2-methoxycyclohexa-2,4-dienone
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 106.037(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.8445(15)
_cell_length_b                   10.7259(5)
_cell_length_c                   11.1126(9)
_cell_measurement_reflns_used    12750
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.42
_cell_measurement_theta_min      1.90
_cell_volume                     1929.6(3)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'STOE IPDS-II'
_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  0.0560
_diffrn_reflns_av_sigmaI/netI    0.0431
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10068
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.28
_diffrn_standards_decay_%        <2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.372
_exptl_absorpt_correction_T_max  0.9769
_exptl_absorpt_correction_T_min  0.8709
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.357
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3782
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0460
_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)+(0.0754P)²+0.1273P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1322
_reflns_number_gt                2715
_reflns_number_total             3782
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hj1088.cif
_cod_data_source_block           I
_cod_original_cell_volume        1929.6(2)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2015257
_cod_database_fobs_code          2015257
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
C C1 0.58033(15) 0.5549(2) 0.2111(2) 0.0460(6) Uani d . 1
C C2 0.50018(17) 0.5839(3) 0.2154(3) 0.0551(7) Uani d . 1
C C3 0.44778(19) 0.6504(3) 0.1201(3) 0.0706(9) Uani d . 1
H H3 0.3948 0.6698 0.1243 0.085 Uiso calc R 1
C C4 0.4730(2) 0.6877(3) 0.0203(3) 0.0801(10) Uani d . 1
H H4 0.4375 0.7343 -0.0425 0.096 Uiso calc R 1
C C5 0.5509(2) 0.6575(3) 0.0099(3) 0.0690(8) Uani d . 1
H H5 0.5677 0.6820 -0.0595 0.083 Uiso calc R 1
C C6 0.60314(17) 0.5899(3) 0.1060(2) 0.0544(6) Uani d . 1
C C7 0.70689(13) 0.4967(2) 0.5165(2) 0.0389(5) Uani d . 1
C C8 0.71827(13) 0.5702(2) 0.6250(2) 0.0405(5) Uani d . 1
H H8 0.6919 0.6470 0.6195 0.049 Uiso calc R 1
C C9 0.76720(13) 0.5310(2) 0.7379(2) 0.0393(5) Uani d . 1
C C10 0.80919(12) 0.4135(2) 0.7498(2) 0.0350(5) Uani d . 1
C C11 0.80026(13) 0.3442(2) 0.6365(2) 0.0362(5) Uani d . 1
C C12 0.74816(14) 0.3857(2) 0.5217(2) 0.0399(5) Uani d . 1
H H12 0.7417 0.3382 0.4496 0.048 Uiso calc R 1
C C13 0.84882(13) 0.2351(2) 0.6384(2) 0.0373(5) Uani d . 1
H H13 0.8428 0.1909 0.5644 0.045 Uiso calc R 1
C C14 0.95897(13) 0.09159(19) 0.75662(19) 0.0340(4) Uani d . 1
C C15 0.96751(14) 0.0380(2) 0.6337(2) 0.0399(5) Uani d . 1
H H15A 0.9701 0.1060 0.5774 0.048 Uiso calc R 1
H H15B 1.0189 -0.0082 0.6499 0.048 Uiso calc R 1
C C16 0.92724(14) -0.0049(2) 0.8336(2) 0.0389(5) Uani d . 1
H H16A 0.9245 0.0315 0.9122 0.047 Uiso calc R 1
H H16B 0.8722 -0.0321 0.7880 0.047 Uiso calc R 1
C C17 1.04417(13) 0.1429(2) 0.8285(2) 0.0403(5) Uani d . 1
H H17A 1.0817 0.0740 0.8587 0.048 Uiso calc R 1
H H17B 1.0664 0.1924 0.7723 0.048 Uiso calc R 1
C C18 0.7495(2) 0.7156(3) 0.8462(3) 0.0683(8) Uani d . 1
H H18A 0.7598 0.7457 0.9305 0.102 Uiso calc R 1
H H18B 0.6910 0.7121 0.8078 0.102 Uiso calc R 1
H H18C 0.7745 0.7710 0.7994 0.102 Uiso calc R 1
Cl Cl1 0.46378(5) 0.52727(10) 0.33563(8) 0.0797(3) Uani d . 1
Cl Cl2 0.70005(5) 0.54926(9) 0.09348(8) 0.0764(3) Uani d . 1
N N1 0.63785(13) 0.4885(2) 0.31082(19) 0.0498(5) Uani d . 1
N N2 0.65194(12) 0.55064(18) 0.40892(19) 0.0435(5) Uani d . 1
N N3 0.90058(11) 0.19559(17) 0.73893(18) 0.0352(4) Uani d . 1
O O1 0.78373(12) 0.59483(17) 0.84753(16) 0.0551(5) Uani d . 1
O O3 0.85420(10) 0.37752(14) 0.85661(14) 0.0420(4) Uani d . 1
O O4 1.03869(11) 0.21784(17) 0.93174(15) 0.0443(4) Uani d . 1
O O5 0.98183(12) -0.10746(16) 0.85653(19) 0.0531(5) Uani d . 1
O O6 0.90118(12) -0.04188(16) 0.57467(18) 0.0471(4) Uani d . 1
H H33 0.9027(16) 0.237(3) 0.799(3) 0.051(8) Uiso d . 1
H H44 1.0575(17) 0.280(3) 0.929(3) 0.050(8) Uiso d . 1
H H55 0.979(2) -0.140(3) 0.920(3) 0.068(10) Uiso d . 1
H H66 0.8821(17) -0.022(3) 0.513(3) 0.043(8) Uiso d . 1
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'
Cl Cl 0.1484 0.1585 '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_publ_flag
C6 C1 C2 117.8(2) ?
C6 C1 N1 120.0(2) y
C2 C1 N1 122.2(2) y
C3 C2 C1 120.6(3) ?
C3 C2 Cl1 119.2(2) ?
C1 C2 Cl1 120.0(2) ?
C4 C3 C2 120.3(3) ?
C4 C3 H3 119.9 ?
C2 C3 H3 119.9 ?
C3 C4 C5 121.2(3) ?
C3 C4 H4 119.4 ?
C5 C4 H4 119.4 ?
C6 C5 C4 118.2(3) ?
C6 C5 H5 120.9 ?
C4 C5 H5 120.9 ?
C1 C6 C5 122.0(3) ?
C1 C6 Cl2 119.3(2) ?
C5 C6 Cl2 118.8(3) ?
C12 C7 C8 120.16(19) ?
C12 C7 N2 126.5(2) ?
C8 C7 N2 113.35(19) y
C9 C8 C7 121.3(2) ?
C9 C8 H8 119.3 ?
C7 C8 H8 119.3 ?
O1 C9 C8 126.3(2) y
O1 C9 C10 112.76(19) ?
C8 C9 C10 120.9(2) ?
O3 C10 C9 120.1(2) ?
O3 C10 C11 123.37(19) y
C9 C10 C11 116.44(18) ?
C12 C11 C13 119.0(2) ?
C12 C11 C10 121.38(19) ?
C13 C11 C10 119.47(18) ?
C7 C12 C11 119.6(2) ?
C7 C12 H12 120.2 ?
C11 C12 H12 120.2 ?
N3 C13 C11 122.2(2) y
N3 C13 H13 118.9 ?
C11 C13 H13 118.9 ?
N3 C14 C15 113.15(17) ?
N3 C14 C16 105.37(17) ?
C15 C14 C16 112.28(18) ?
N3 C14 C17 107.04(17) ?
C15 C14 C17 107.13(18) y
C16 C14 C17 111.82(18) ?
O6 C15 C14 112.68(19) ?
O6 C15 H15A 109.1 ?
C14 C15 H15A 109.1 ?
O6 C15 H15B 109.1 ?
C14 C15 H15B 109.1 ?
H15A C15 H15B 107.8 ?
O5 C16 C14 108.52(19) ?
O5 C16 H16A 110.0 ?
C14 C16 H16A 110.0 ?
O5 C16 H16B 110.0 ?
C14 C16 H16B 110.0 ?
H16A C16 H16B 108.4 ?
O4 C17 C14 111.17(18) ?
O4 C17 H17A 109.4 ?
C14 C17 H17A 109.4 ?
O4 C17 H17B 109.4 ?
C14 C17 H17B 109.4 ?
H17A C17 H17B 108.0 ?
O1 C18 H18A 109.5 ?
O1 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
O1 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
N2 N1 C1 109.5(2) ?
N1 N2 C7 116.28(19) ?
C13 N3 C14 129.6(2) y
C13 N3 H33 114(2) ?
C14 N3 H33 116(2) ?
C9 O1 C18 118.02(19) ?
C17 O4 H44 111(2) ?
C16 O5 H55 107(2) ?
C15 O6 H66 111(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 1.378(4) ?
C1 C2 1.399(4) ?
C1 N1 1.443(3) y
C2 C3 1.375(4) ?
C2 Cl1 1.727(3) y
C3 C4 1.354(5) ?
C3 H3 0.9300 ?
C4 C5 1.387(5) ?
C4 H4 0.9300 ?
C5 C6 1.386(4) ?
C5 H5 0.9300 ?
C6 Cl2 1.732(3) y
C7 C12 1.372(3) y
C7 C8 1.409(3) y
C7 N2 1.417(3) y
C8 C9 1.364(3) y
C8 H8 0.9300 ?
C9 O1 1.357(3) y
C9 C10 1.434(3) y
C10 O3 1.279(3) y
C10 C11 1.434(3) y
C11 C12 1.406(3) y
C11 C13 1.425(3) y
C12 H12 0.9300 ?
C13 N3 1.284(3) y
C13 H13 0.9300 ?
C14 N3 1.464(3) y
C14 C15 1.525(3) ?
C14 C16 1.530(3) ?
C14 C17 1.538(3) ?
C15 O6 1.417(3) ?
C15 H15A 0.9700 ?
C15 H15B 0.9700 ?
C16 O5 1.411(3) ?
C16 H16A 0.9700 ?
C16 H16B 0.9700 ?
C17 O4 1.425(3) ?
C17 H17A 0.9700 ?
C17 H17B 0.9700 ?
C18 O1 1.417(3) y
C18 H18A 0.9600 ?
C18 H18B 0.9600 ?
C18 H18C 0.9600 ?
N1 N2 1.243(3) y
N3 H33 0.79(3) ?
O4 H44 0.74(3) ?
O5 H55 0.80(4) ?
O6 H66 0.70(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N3 H33 O3 . 0.79(3) 1.90(3) 2.587(2) 144(3)
O4 H44 O6 2_756 0.74(3) 2.04(3) 2.777(3) 174(3)
O5 H55 O4 3_757 0.80(4) 1.94(4) 2.740(3) 176(3)
O6 H66 O1 4_565 0.70(3) 2.25(3) 2.802(2) 137(3)
O6 H66 O3 4_565 0.70(3) 2.28(3) 2.923(2) 153(3)
C17 H17A G1 2_555 0.97000 2.9471000 3.798(2) 147.06000
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
C6 C1 C2 C3 -3.1(4) ?
N1 C1 C2 C3 178.2(3) ?
C6 C1 C2 Cl1 172.6(2) ?
N1 C1 C2 Cl1 -6.2(3) ?
C1 C2 C3 C4 0.6(5) ?
Cl1 C2 C3 C4 -175.1(3) ?
C2 C3 C4 C5 1.6(5) ?
C3 C4 C5 C6 -1.2(5) ?
C2 C1 C6 C5 3.4(4) ?
N1 C1 C6 C5 -177.7(2) ?
C2 C1 C6 Cl2 -176.9(2) ?
N1 C1 C6 Cl2 1.9(3) ?
C4 C5 C6 C1 -1.4(4) ?
C4 C5 C6 Cl2 179.0(2) ?
C12 C7 C8 C9 -2.9(4) ?
N2 C7 C8 C9 178.0(2) ?
C7 C8 C9 O1 178.7(2) ?
C7 C8 C9 C10 0.3(4) ?
O1 C9 C10 O3 2.1(3) ?
C8 C9 C10 O3 -179.3(2) ?
O1 C9 C10 C11 -175.4(2) ?
C8 C9 C10 C11 3.2(3) ?
O3 C10 C11 C12 178.1(2) ?
C9 C10 C11 C12 -4.5(3) ?
O3 C10 C11 C13 -5.7(3) ?
C9 C10 C11 C13 171.7(2) ?
C8 C7 C12 C11 1.6(3) ?
N2 C7 C12 C11 -179.4(2) ?
C13 C11 C12 C7 -174.0(2) ?
C10 C11 C12 C7 2.1(3) ?
C12 C11 C13 N3 176.5(2) ?
C10 C11 C13 N3 0.3(3) y
N3 C14 C15 O6 -78.6(2) ?
C16 C14 C15 O6 40.5(2) ?
C17 C14 C15 O6 163.68(17) ?
N3 C14 C16 O5 -178.82(18) ?
C15 C14 C16 O5 57.6(2) ?
C17 C14 C16 O5 -62.9(2) ?
N3 C14 C17 O4 46.1(2) ?
C15 C14 C17 O4 167.76(17) ?
C16 C14 C17 O4 -68.8(2) ?
C6 C1 N1 N2 119.3(3) ?
C2 C1 N1 N2 -62.0(3) ?
C1 N1 N2 C7 179.2(2) y
C12 C7 N2 N1 2.7(4) ?
C8 C7 N2 N1 -178.3(2) ?
C11 C13 N3 C14 -175.4(2) ?
C15 C14 N3 C13 10.7(3) ?
C16 C14 N3 C13 -112.3(2) ?
C17 C14 N3 C13 128.5(2) ?
C8 C9 O1 C18 -2.0(4) ?
C10 C9 O1 C18 176.5(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654035
