#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:02:04 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179552 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/21/4502180.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_4502180
loop_
_publ_author_name
'Macháček, Vladimír'
'Bertolasi, Valerio'
'Šim°unek, Petr'
'Svobodová, Markéta'
'Svoboda, Jan'
'C̆ernošková, Eva'
_publ_section_title
;
 A Three-Dimensional Channel Supramolecular Architecture Based on
 3-Amino-2-(4-dimethylaminophenyldiazenyl)-1-phenylbut-2-en-1-one and
 Aromatic Guests†
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              85
_journal_paper_doi               10.1021/cg900295n
_journal_volume                  10
_journal_year                    2010
_chemical_formula_moiety         'C18 H20 N4 O'
_chemical_formula_sum            'C18 H20 N4 O'
_chemical_formula_weight         308.38
_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                 90.9820(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9279(2)
_cell_length_b                   10.8905(2)
_cell_length_c                   16.0206(4)
_cell_measurement_reflns_used    3716
_cell_measurement_temperature    295
_cell_measurement_theta_max      27.0
_cell_measurement_theta_min      3.2
_cell_volume                     1731.89(6)
_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), PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0256
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12621
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.0
_diffrn_reflns_theta_min         3.2
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.31
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.049(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         3760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0569
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1004P)²+0.2590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1590
_refine_ls_wR_factor_ref         0.1814
_reflns_number_gt                2863
_reflns_number_total             3760
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            cg900295n_si_001.cif
_cod_data_source_block           (1a)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4502180
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
O1 O 0.37936(15) 0.30186(12) -0.20164(7) 0.0819(4) Uani 1 1 d .
N1 N 0.66538(14) 0.09636(13) -0.02455(8) 0.0629(4) Uani 1 1 d .
H1 H 0.677(14) 0.014(15) -0.042(10) 0.075 Uiso 0.14(3) 1 d P
N2 N 0.56906(13) 0.17074(11) -0.04098(8) 0.0593(4) Uani 1 1 d .
N3 N 0.61062(17) -0.01607(15) -0.16684(11) 0.0762(4) Uani 1 1 d .
H31 H 0.663(3) -0.013(2) -0.117(2) 0.091 Uiso 0.86(3) 1 d P
N4 N 0.93004(19) 0.1661(2) 0.28440(11) 0.1035(7) Uani 1 1 d .
C1 C 0.50213(16) 0.16265(14) -0.11717(9) 0.0595(4) Uani 1 1 d .
C2 C 0.51907(17) 0.07029(15) -0.17775(10) 0.0630(4) Uani 1 1 d .
C3 C 0.40943(17) 0.26435(14) -0.13110(9) 0.0613(4) Uani 1 1 d .
C4 C 0.4325(2) 0.0609(2) -0.25469(13) 0.0767(5) Uani 1 1 d .
C5 C 0.34586(16) 0.32484(14) -0.05773(9) 0.0611(4) Uani 1 1 d .
C6 C 0.2940(2) 0.25762(19) 0.00679(12) 0.0807(5) Uani 1 1 d .
C7 C 0.2244(3) 0.3148(3) 0.06941(15) 0.1043(8) Uani 1 1 d .
C8 C 0.2110(3) 0.4407(3) 0.06905(16) 0.1049(8) Uani 1 1 d .
C9 C 0.2630(3) 0.5081(2) 0.00615(17) 0.1089(8) Uani 1 1 d .
C10 C 0.3292(2) 0.45086(18) -0.05804(14) 0.0855(6) Uani 1 1 d .
C11 C 0.72781(16) 0.11753(14) 0.05441(10) 0.0592(4) Uani 1 1 d .
C12 C 0.6787(2) 0.19779(17) 0.11432(11) 0.0703(5) Uani 1 1 d .
C13 C 0.7456(2) 0.21401(19) 0.18902(12) 0.0775(5) Uani 1 1 d .
C14 C 0.86550(18) 0.1517(2) 0.20820(11) 0.0752(5) Uani 1 1 d .
C15 C 0.9137(2) 0.0723(3) 0.14723(13) 0.0889(6) Uani 1 1 d .
C16 C 0.84579(19) 0.0552(2) 0.07249(12) 0.0794(5) Uani 1 1 d .
C17 C 0.8790(4) 0.2537(3) 0.34380(16) 0.1304(11) Uani 1 1 d .
H171 H 0.9375 0.2559 0.3921 0.157 Uiso 1 1 calc R
H172 H 0.7902 0.2297 0.3601 0.157 Uiso 1 1 calc R
H173 H 0.8754 0.3337 0.3187 0.157 Uiso 1 1 calc R
C18 C 1.0583(3) 0.1085(6) 0.2990(2) 0.185(2) Uani 1 1 d .
H181 H 1.1211 0.1369 0.2584 0.222 Uiso 1 1 calc R
H182 H 1.0486 0.0211 0.2945 0.222 Uiso 1 1 calc R
H183 H 1.0911 0.1292 0.3540 0.222 Uiso 1 1 calc R
H32 H 0.615(2) -0.079(2) -0.2063(15) 0.091(6) Uiso 1 1 d .
H41 H 0.460(3) 0.121(2) -0.2988(16) 0.102(7) Uiso 1 1 d .
H42 H 0.438(2) -0.020(3) -0.2783(16) 0.105(7) Uiso 1 1 d .
H43 H 0.339(3) 0.080(3) -0.2440(17) 0.118(9) Uiso 1 1 d .
H6 H 0.307(3) 0.167(3) 0.0064(16) 0.114(8) Uiso 1 1 d .
H7 H 0.184(3) 0.263(3) 0.112(2) 0.138(10) Uiso 1 1 d .
H8 H 0.166(3) 0.487(3) 0.1162(19) 0.131(9) Uiso 1 1 d .
H9 H 0.247(4) 0.597(4) 0.0014(19) 0.148(11) Uiso 1 1 d .
H10 H 0.370(2) 0.504(2) -0.1068(15) 0.103(7) Uiso 1 1 d .
H12 H 0.598(2) 0.2432(19) 0.1012(12) 0.076(5) Uiso 1 1 d .
H13 H 0.716(2) 0.272(2) 0.2287(15) 0.105(7) Uiso 1 1 d .
H15 H 0.993(3) 0.030(2) 0.1556(15) 0.108(7) Uiso 1 1 d .
H16 H 0.883(3) 0.001(3) 0.0304(16) 0.111(8) 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
N2 N1 C11 113.26(13)
N2 N1 H1 129(9)
C11 N1 H1 112(9)
N1 N2 C1 119.23(13)
C2 N3 H31 117.0(17)
C2 N3 H32 118.2(14)
H31 N3 H32 125(2)
C14 N4 C18 119.5(2)
C14 N4 C17 119.7(2)
C18 N4 C17 120.1(2)
N2 C1 C2 126.30(14)
N2 C1 C3 112.34(13)
C2 C1 C3 121.35(14)
N3 C2 C1 120.54(15)
N3 C2 C4 116.51(16)
C1 C2 C4 122.89(16)
O1 C3 C1 122.36(15)
O1 C3 C5 118.37(14)
C1 C3 C5 119.27(13)
C2 C4 H41 111.9(14)
C2 C4 H42 110.5(15)
H41 C4 H42 108(2)
C2 C4 H43 112.2(16)
H41 C4 H43 105(2)
H42 C4 H43 109(2)
C6 C5 C10 119.04(17)
C6 C5 C3 121.66(15)
C10 C5 C3 119.09(15)
C5 C6 C7 120.4(2)
C5 C6 H6 118.2(15)
C7 C6 H6 121.3(15)
C6 C7 C8 119.8(2)
C6 C7 H7 117.8(19)
C8 C7 H7 122.4(19)
C9 C8 C7 120.3(2)
C9 C8 H8 117.3(17)
C7 C8 H8 122.4(17)
C8 C9 C10 120.1(2)
C8 C9 H9 122.0(19)
C10 C9 H9 117.6(19)
C9 C10 C5 120.3(2)
C9 C10 H10 120.1(14)
C5 C10 H10 119.6(14)
C16 C11 C12 118.04(16)
C16 C11 N1 117.62(15)
C12 C11 N1 124.33(14)
C13 C12 C11 120.83(17)
C13 C12 H12 121.0(12)
C11 C12 H12 118.2(12)
C12 C13 C14 121.81(18)
C12 C13 H13 121.3(15)
C14 C13 H13 116.8(15)
N4 C14 C15 122.05(19)
N4 C14 C13 121.36(19)
C15 C14 C13 116.57(17)
C16 C15 C14 121.60(18)
C16 C15 H15 117.6(16)
C14 C15 H15 120.8(16)
C15 C16 C11 121.14(18)
C15 C16 H16 120.0(16)
C11 C16 H16 118.9(16)
N4 C17 H171 109.5
N4 C17 H172 109.5
H171 C17 H172 109.5
N4 C17 H173 109.5
H171 C17 H173 109.5
H172 C17 H173 109.5
N4 C18 H181 109.5
N4 C18 H182 109.5
H181 C18 H182 109.5
N4 C18 H183 109.5
H181 C18 H183 109.5
H182 C18 H183 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.2335(18)
N1 N2 1.2772(19)
N1 C11 1.418(2)
N1 H1 0.95(16)
N2 C1 1.3826(19)
N3 C2 1.317(2)
N3 H31 0.95(3)
N3 H32 0.94(2)
N4 C14 1.378(2)
N4 C18 1.435(4)
N4 C17 1.445(4)
C1 C2 1.410(2)
C1 C3 1.455(2)
C2 C4 1.494(2)
C3 C5 1.496(2)
C4 H41 1.01(3)
C4 H42 0.96(3)
C4 H43 0.97(3)
C5 C6 1.374(2)
C5 C10 1.382(3)
C6 C7 1.377(3)
C6 H6 0.99(3)
C7 C8 1.378(4)
C7 H7 0.97(3)
C8 C9 1.356(4)
C8 H8 1.02(3)
C9 C10 1.379(3)
C9 H9 0.99(4)
C10 H10 1.06(3)
C11 C16 1.380(2)
C11 C12 1.393(2)
C12 C13 1.370(3)
C12 H12 0.96(2)
C13 C14 1.400(3)
C13 H13 0.95(3)
C14 C15 1.396(3)
C15 C16 1.377(3)
C15 H15 0.92(3)
C16 H16 0.98(3)
C17 H171 0.9600
C17 H172 0.9600
C17 H173 0.9600
C18 H181 0.9600
C18 H182 0.9600
C18 H183 0.9600
