data_2203215
loop_
_publ_author_name
'Karaday\?i, Nevzat'
'Turgut, G\"unseli'
'Odaba\;so\(glu, Mustafa '
'B\"uy\"ukg\"ung\"or, Orhan'
_publ_section_title
;
4-(4'-Methylphenylazo)-2-allylphenol monohydrate
;
_journal_issue                 2
_journal_name_full             'Acta Crystallographica, Section E'
_journal_page_first            o176
_journal_page_last             o178
_journal_volume                60
_journal_year                  2004
_chemical_formula_moiety       'C16 H16 N2 O , H2 O'
_chemical_formula_sum          'C16 H18 N2 O2'
_chemical_formula_weight       270.32
_chemical_melting_point        ?
_chemical_name_common          ?
_chemical_name_systematic
;
p-[p^'^-methylphenylazo]-o-allylphenol monohydrate
;
_symmetry_cell_setting         orthorhombic
_symmetry_space_group_name_Hall '-P 2n 2ab'
_symmetry_space_group_name_H-M 'P b c n'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary   direct
_atom_sites_solution_secondary difmap
_cell_angle_alpha              90.00
_cell_angle_beta               90.00
_cell_angle_gamma              90.00
_cell_formula_units_Z          8
_cell_length_a                 27.2961(9)
_cell_length_b                 14.4293(17)
_cell_length_c                 7.568(4)
_cell_measurement_reflns_used  3655
_cell_measurement_temperature  293
_cell_measurement_theta_max    21.55
_cell_measurement_theta_min    1.49
_cell_volume                   2980.8(16)
_computing_cell_refinement     X-AREA
_computing_data_collection     'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction      'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996); PLUTON (Spek, 1997)
;
_computing_publication_material
;
WinGX (Farrugia, 1999)
;
_computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution  'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature    293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device     '2-circle goniometer'
_diffrn_measurement_device_type 'STOE IPDS 2'
_diffrn_measurement_method     \w?
_diffrn_radiation_monochromator 'plane graphite'
_diffrn_radiation_source       'fine-focus sealed tube'
_diffrn_radiation_type         MoK\a
_diffrn_radiation_wavelength   0.71073
_diffrn_reflns_av_R_equivalents 0.1754
_diffrn_reflns_av_sigmaI/netI  0.1367
_diffrn_reflns_limit_h_max     32
_diffrn_reflns_limit_h_min     -32
_diffrn_reflns_limit_k_max     17
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_l_max     8
_diffrn_reflns_limit_l_min     -8
_diffrn_reflns_number          17874
_diffrn_reflns_theta_full      25.00
_diffrn_reflns_theta_max       25.00
_diffrn_reflns_theta_min       1.49
_diffrn_standards_decay_%      none
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time ?
_diffrn_standards_number       0
_exptl_absorpt_coefficient_mu  0.080
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_type none
_exptl_absorpt_process_details ?
_exptl_crystal_colour          'light brown'
_exptl_crystal_density_diffrn  1.205
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     prism
_exptl_crystal_F_000           1152
_exptl_crystal_size_max        0.30
_exptl_crystal_size_mid        0.17
_exptl_crystal_size_min        0.10
_refine_diff_density_max       0.224
_refine_diff_density_min       -0.188
_refine_ls_extinction_coef     0.0040(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method   SHELXL
_refine_ls_goodness_of_fit_ref 0.882
_refine_ls_hydrogen_treatment  mixed
_refine_ls_matrix_type         full
_refine_ls_number_parameters   202
_refine_ls_number_reflns       2629
_refine_ls_number_restraints   29
_refine_ls_restrained_S_all    0.947
_refine_ls_R_factor_all        0.2183
_refine_ls_R_factor_gt         0.0685
_refine_ls_shift/su_max        0.030
_refine_ls_shift/su_mean       0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.062P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.1482
_refine_ls_wR_factor_ref       0.1799
_reflns_number_gt              806
_reflns_number_total           2629
_reflns_threshold_expression   'I >2\s(I)'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
loop_
_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
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C15A 0.4384(3) 0.3755(6) 0.4272(17) 0.0800(17) Uani d PDU 0.677(10) A 1 C
H15A 0.4437 0.3944 0.3112 0.096 Uiso calc PR 0.677(10) A 1 H
C15B 0.4303(6) 0.3852(13) 0.559(3) 0.0799(17) Uani d PDU 0.323(10) A 2 C
H15B 0.4239 0.4169 0.6640 0.096 Uiso calc PR 0.323(10) A 2 H
O1 0.29396(16) 0.3165(2) 0.3329(6) 0.0769(13) Uani d . 1 . . O
H1 0.2746 0.3106 0.2509 0.115 Uiso calc R 1 . . H
O2 0.21137(17) 0.2925(3) 0.1485(7) 0.0819(14) Uani d D 1 . . O
N1 0.33785(17) 0.6899(3) 0.4275(6) 0.0610(13) Uani d . 1 . . N
N2 0.37711(18) 0.7089(3) 0.5103(6) 0.0664(14) Uani d . 1 . . N
C1 0.3051(2) 0.4089(4) 0.3547(7) 0.0581(16) Uani d . 1 . . C
C2 0.3514(2) 0.4296(4) 0.4216(7) 0.0575(15) Uani d D 1 A . C
C3 0.3630(2) 0.5233(4) 0.4480(8) 0.0623(16) Uani d . 1 . . C
H3 0.3934 0.5398 0.4938 0.075 Uiso calc R 1 . . H
C4 0.3285(2) 0.5923(4) 0.4048(7) 0.0578(16) Uani d . 1 . . C
C5 0.2850(2) 0.5685(4) 0.3334(8) 0.0694(17) Uani d . 1 . . C
H5 0.2631 0.6148 0.3006 0.083 Uiso calc R 1 . . H
C6 0.2722(2) 0.4767(4) 0.3080(8) 0.0656(17) Uani d . 1 . . C
H6 0.2419 0.4611 0.2602 0.079 Uiso calc R 1 . . H
C7 0.3835(2) 0.8079(4) 0.5334(7) 0.0596(16) Uani d . 1 . . C
C8 0.4308(3) 0.8356(4) 0.5647(8) 0.0723(18) Uani d . 1 . . C
H8 0.4557 0.7920 0.5755 0.087 Uiso calc R 1 . . H
C9 0.4409(2) 0.9290(4) 0.5799(8) 0.0739(18) Uani d . 1 . . C
H9 0.4730 0.9479 0.5992 0.089 Uiso calc R 1 . . H
C10 0.4043(3) 0.9954(4) 0.5672(8) 0.0654(17) Uani d . 1 . . C
C11 0.3575(3) 0.9637(4) 0.5412(8) 0.0743(19) Uani d . 1 . . C
H11 0.3322 1.0068 0.5360 0.089 Uiso calc R 1 . . H
C12 0.3462(2) 0.8717(4) 0.5227(8) 0.0683(18) Uani d . 1 . . C
H12 0.3141 0.8529 0.5032 0.082 Uiso calc R 1 . . H
C13 0.4161(2) 1.0971(4) 0.5803(8) 0.087(2) Uani d . 1 . . C
H13A 0.4049 1.1206 0.6919 0.130 Uiso calc R 1 . . H
H13B 0.4000 1.1299 0.4862 0.130 Uiso calc R 1 . . H
H13C 0.4509 1.1058 0.5710 0.130 Uiso calc R 1 . . H
C14 0.3876(2) 0.3526(4) 0.4624(9) 0.0797(16) Uani d DU 1 . . C
H14A 0.3845 0.3361 0.5861 0.096 Uiso calc R 1 A 1 H
H14B 0.3789 0.2985 0.3932 0.096 Uiso calc R 1 A 1 H
C16 0.4765(3) 0.3755(6) 0.5178(14) 0.168(4) Uani d DU 1 . . C
H16A 0.4753 0.3578 0.6359 0.202 Uiso calc R 1 A 1 H
H16B 0.5061 0.3933 0.4674 0.202 Uiso calc R 1 A 1 H
H1A 0.200(6) 0.240(6) 0.19(2) 0.38(9) Uiso d D 1 . . H
H1B 0.211(5) 0.288(9) 0.037(3) 0.29(7) Uiso d D 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C15A 0.080(3) 0.058(3) 0.102(4) 0.003(3) 0.000(3) 0.000(3)
C15B 0.080(3) 0.058(3) 0.102(4) 0.003(3) -0.001(3) 0.000(3)
O1 0.098(4) 0.055(3) 0.078(3) -0.011(2) -0.008(2) -0.005(2)
O2 0.091(3) 0.074(3) 0.081(3) -0.017(3) -0.004(3) -0.009(3)
N1 0.075(4) 0.055(3) 0.053(3) -0.004(3) -0.002(3) 0.003(3)
N2 0.075(4) 0.059(3) 0.066(3) -0.007(3) -0.002(3) 0.003(3)
C1 0.071(5) 0.051(4) 0.052(4) 0.000(3) 0.006(3) 0.007(3)
C2 0.058(4) 0.057(4) 0.058(4) -0.003(3) 0.001(3) 0.001(3)
C3 0.068(4) 0.058(4) 0.061(4) -0.001(3) 0.006(3) 0.001(3)
C4 0.073(5) 0.051(4) 0.049(4) -0.003(3) -0.001(3) 0.000(3)
C5 0.074(5) 0.062(4) 0.072(4) 0.001(4) -0.008(4) 0.005(4)
C6 0.054(4) 0.067(4) 0.076(4) -0.009(3) -0.008(3) 0.005(4)
C7 0.068(4) 0.056(4) 0.055(4) -0.005(4) 0.006(3) 0.003(3)
C8 0.088(5) 0.062(4) 0.067(4) 0.000(4) -0.003(4) -0.002(4)
C9 0.072(5) 0.073(5) 0.077(5) -0.015(4) -0.010(4) 0.005(4)
C10 0.084(5) 0.060(4) 0.052(4) -0.003(4) 0.005(4) -0.007(3)
C11 0.086(5) 0.072(5) 0.065(5) 0.008(4) 0.003(4) -0.013(4)
C12 0.074(5) 0.055(4) 0.075(5) 0.004(4) -0.001(3) -0.011(4)
C13 0.122(6) 0.061(4) 0.077(5) -0.011(4) 0.017(4) -0.004(4)
C14 0.080(3) 0.058(3) 0.102(4) 0.003(3) -0.001(3) 0.000(3)
C16 0.171(4) 0.087(9) 0.132(12) 0.007(6) -0.031(5) -0.011(9)
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C16 C15A C14 . . 134.2(11) ?
C16 C15A H15A . . 112.9 ?
C14 C15A H15A . . 112.9 ?
C16 C15B C14 . . 128.0(18) ?
C16 C15B H15B . . 116.0 ?
C14 C15B H15B . . 116.0 ?
C1 O1 H1 . . 109.5 ?
H1A O2 H1B . . 105(10) ?
N2 N1 C4 . . 114.8(5) yes
N1 N2 C7 . . 111.9(5) yes
C6 C1 O1 . . 120.9(6) yes
C6 C1 C2 . . 122.2(5) ?
O1 C1 C2 . . 116.9(5) yes
C1 C2 C3 . . 117.7(5) ?
C1 C2 C14 . . 120.5(5) ?
C3 C2 C14 . . 121.8(5) ?
C2 C3 C4 . . 119.7(5) ?
C2 C3 H3 . . 120.2 ?
C4 C3 H3 . . 120.2 ?
C5 C4 C3 . . 120.1(5) yes
C5 C4 N1 . . 117.0(5) yes
C3 C4 N1 . . 122.9(5) ?
C4 C5 C6 . . 121.5(6) ?
C4 C5 H5 . . 119.3 ?
C6 C5 H5 . . 119.3 ?
C1 C6 C5 . . 118.7(5) ?
C1 C6 H6 . . 120.6 ?
C5 C6 H6 . . 120.6 ?
C8 C7 C12 . . 120.8(6) ?
C8 C7 N2 . . 114.8(6) yes
C12 C7 N2 . . 124.4(6) yes
C7 C8 C9 . . 119.1(6) ?
C7 C8 H8 . . 120.5 ?
C9 C8 H8 . . 120.5 ?
C8 C9 C10 . . 121.7(6) ?
C8 C9 H9 . . 119.2 ?
C10 C9 H9 . . 119.2 ?
C11 C10 C9 . . 116.8(6) ?
C11 C10 C13 . . 122.3(6) ?
C9 C10 C13 . . 121.0(6) ?
C12 C11 C10 . . 123.2(6) ?
C12 C11 H11 . . 118.4 ?
C10 C11 H11 . . 118.4 ?
C11 C12 C7 . . 118.4(6) ?
C11 C12 H12 . . 120.8 ?
C7 C12 H12 . . 120.8 ?
C10 C13 H13A . . 109.5 ?
C10 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C10 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C15A C14 C2 . . 114.7(6) ?
C15B C14 C2 . . 112.8(9) ?
C15A C14 H14A . . 108.6 ?
C2 C14 H14A . . 108.6 ?
C15A C14 H14B . . 108.6 ?
C2 C14 H14B . . 108.6 ?
H14A C14 H14B . . 107.6 ?
C15A C16 H16A . . 120.0 ?
C15A C16 H16B . . 120.0 ?
H16A C16 H16B . . 120.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C15A C16 . 1.247(10) ?
C15A C14 . 1.449(9) ?
C15A H15A . 0.9300 ?
C15B C16 . 1.309(15) ?
C15B C14 . 1.454(15) ?
C15B H15B . 0.9300 ?
O1 C1 . 1.378(6) yes
O1 H1 . 0.8200 ?
O2 H1A . 0.87(2) ?
O2 H1B . 0.84(2) ?
N1 N2 . 1.272(5) yes
N1 C4 . 1.441(6) yes
N2 C7 . 1.450(6) yes
C1 C6 . 1.374(7) yes
C1 C2 . 1.392(7) yes
C2 C3 . 1.403(7) yes
C2 C14 . 1.520(7) yes
C3 C4 . 1.410(7) yes
C3 H3 . 0.9300 ?
C4 C5 . 1.348(7) yes
C5 C6 . 1.383(7) yes
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.372(7) ?
C7 C12 . 1.374(7) ?
C8 C9 . 1.381(7) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.387(7) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.370(7) ?
C10 C13 . 1.506(7) ?
C11 C12 . 1.370(7) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C16 H16A . 0.9300 ?
C16 H16B . 0.9300 ?
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
O1 H1 O2 . 0.82 1.91 2.674(6) 154.8
O2 H1A N1 7_655 0.87(2) 2.22(12) 2.908(7) 136(14)
O2 H1B O1 2_554 0.84(2) 2.17(9) 2.864(6) 140(12)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4 N1 N2 C7 . . . . -178.1(5) yes
C6 C1 C2 C3 . . . . 2.7(8) ?
O1 C1 C2 C3 . . . . -178.7(5) ?
C6 C1 C2 C14 . . . . -176.7(6) ?
O1 C1 C2 C14 . . . . 1.8(8) ?
C1 C2 C3 C4 . . . . -0.7(8) ?
C14 C2 C3 C4 . . . . 178.7(5) ?
C2 C3 C4 C5 . . . . -2.0(8) ?
C2 C3 C4 N1 . . . . -179.7(5) ?
N2 N1 C4 C5 . . . . 173.6(5) ?
N2 N1 C4 C3 . . . . -8.6(7) ?
C3 C4 C5 C6 . . . . 2.9(9) ?
N1 C4 C5 C6 . . . . -179.3(5) ?
O1 C1 C6 C5 . . . . 179.6(5) ?
C2 C1 C6 C5 . . . . -2.0(9) ?
C4 C5 C6 C1 . . . . -0.9(9) ?
N1 N2 C7 C8 . . . . -158.7(5) ?
N1 N2 C7 C12 . . . . 20.2(8) ?
C12 C7 C8 C9 . . . . -2.0(9) ?
N2 C7 C8 C9 . . . . 176.9(5) ?
C7 C8 C9 C10 . . . . 1.0(10) ?
C8 C9 C10 C11 . . . . 0.9(10) ?
C8 C9 C10 C13 . . . . -178.7(6) ?
C9 C10 C11 C12 . . . . -2.0(10) ?
C13 C10 C11 C12 . . . . 177.6(6) ?
C10 C11 C12 C7 . . . . 1.1(10) ?
C8 C7 C12 C11 . . . . 1.0(9) ?
N2 C7 C12 C11 . . . . -177.8(6) ?
C16 C15A C14 C15B . . . . 26.8(13) ?
C16 C15A C14 C2 . . . . 124.0(11) ?
C16 C15B C14 C15A . . . . -23.0(12) ?
C16 C15B C14 C2 . . . . -125.2(16) ?
C1 C2 C14 C15A . . . . 144.4(7) ?
C3 C2 C14 C15A . . . . -35.1(9) ?
C1 C2 C14 C15B . . . . -169.8(11) ?
C3 C2 C14 C15B . . . . 10.7(12) ?
C14 C15A C16 C15B . . . . -26.8(13) ?
C14 C15B C16 C15A . . . . 24.2(13) ?