#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/31/2203184.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_2203184
loop_
_publ_author_name
'Atalay, Şehriman'
'Çoruh, Ufuk'
'Akdemir, Nesuhi'
'Aǧar, Erbil'
_publ_section_title
;
 C---H···π interactions in
 4,5-bis(2-isopropyl-5-methylphenoxy)phthalonitrile
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o303
_journal_page_last               o305
_journal_paper_doi               10.1107/S1600536804001758
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C28 H28 N2 O2'
_chemical_formula_moiety         'C28 H28 N2 O2'
_chemical_formula_sum            'C28 H28 N2 O2'
_chemical_formula_weight         424.52
_chemical_melting_point          412
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                93.919(8)
_cell_angle_beta                 101.078(8)
_cell_angle_gamma                95.278(8)
_cell_formula_units_Z            2
_cell_length_a                   9.268(9)
_cell_length_b                   10.150(10)
_cell_length_c                   13.115(13)
_cell_measurement_reflns_used    10727
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.61
_cell_measurement_theta_min      2.02
_cell_volume                     1201(2)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA(Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED (Stoe & Cie, 2002)'
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and
CAMERON (Watkin et al., 1993)
;
_computing_publication_material
'WinGX (Farrugia, 1999) and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       ω
_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  0.059
_diffrn_reflns_av_sigmaI/netI    0.054
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20244
_diffrn_reflns_theta_full        27.77
_diffrn_reflns_theta_max         27.77
_diffrn_reflns_theta_min         2.02
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.12
_refine_ls_extinction_coef       0.022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   0.872
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         5615
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.872
_refine_ls_R_factor_all          0.0970
_refine_ls_R_factor_gt           0.0438
_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)+(0.0657P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1199
_reflns_number_gt                2920
_reflns_number_total             5615
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn6116.cif
_cod_data_source_block           I
_cod_database_code               2203184
_cod_database_fobs_code          2203184
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_type_symbol
C1 0.37449(17) 0.48474(15) 0.15623(12) 0.0488(4) Uani d . 1 C
C2 0.24312(17) 0.42230(15) 0.09327(11) 0.0485(4) Uani d . 1 C
C3 0.16225(18) 0.32049(16) 0.12937(12) 0.0537(4) Uani d . 1 C
H3 0.0767 0.2773 0.0868 0.064 Uiso calc R 1 H
C4 0.20871(17) 0.28305(15) 0.22861(11) 0.0489(4) Uani d . 1 C
C5 0.33592(16) 0.34841(15) 0.29231(11) 0.0463(4) Uani d . 1 C
C6 0.41920(17) 0.44672(15) 0.25591(12) 0.0501(4) Uani d . 1 C
H6 0.5059 0.4879 0.2983 0.060 Uiso calc R 1 H
N7 0.53188(19) 0.66831(17) 0.08891(13) 0.0834(5) Uani d . 1 N
C7 0.46176(19) 0.58752(17) 0.11873(13) 0.0589(4) Uani d . 1 C
N8 0.1486(2) 0.50187(18) -0.08687(13) 0.0849(5) Uani d . 1 N
O1 0.14025(13) 0.18296(11) 0.27130(8) 0.0647(3) Uani d . 1 O
O2 0.38319(12) 0.30799(11) 0.38988(8) 0.0539(3) Uani d . 1 O
C8 0.19106(19) 0.46558(17) -0.00766(13) 0.0595(4) Uani d . 1 C
C9 0.00594(17) 0.11372(16) 0.21740(11) 0.0504(4) Uani d . 1 C
C10 -0.1186(2) 0.17933(17) 0.20045(12) 0.0589(4) Uani d . 1 C
H10 -0.1108 0.2703 0.2183 0.071 Uiso calc R 1 H
C11 -0.25558(19) 0.11133(19) 0.15704(13) 0.0623(5) Uani d . 1 C
C12 -0.2605(2) -0.02300(19) 0.13230(14) 0.0651(5) Uani d . 1 C
H12 -0.3510 -0.0715 0.1034 0.078 Uiso calc R 1 H
C13 -0.1354(2) -0.08734(18) 0.14926(13) 0.0619(5) Uani d . 1 C
H13 -0.1433 -0.1782 0.1309 0.074 Uiso calc R 1 H
C14 0.00345(17) -0.02089(16) 0.19311(12) 0.0525(4) Uani d . 1 C
C15 0.1422(2) -0.09005(18) 0.21128(14) 0.0650(5) Uani d . 1 C
H15 0.2121 -0.0376 0.2685 0.078 Uiso calc R 1 H
C16 0.1198(3) -0.2280(3) 0.2446(3) 0.1204(10) Uani d . 1 C
H16A 0.2121 -0.2660 0.2547 0.181 Uiso calc R 1 H
H16B 0.0487 -0.2819 0.1917 0.181 Uiso calc R 1 H
H16C 0.0844 -0.2242 0.3088 0.181 Uiso calc R 1 H
C17 0.2128(3) -0.0889(4) 0.1166(2) 0.1372(12) Uani d . 1 C
H17A 0.3009 -0.1331 0.1293 0.206 Uiso calc R 1 H
H17B 0.2376 0.0013 0.1030 0.206 Uiso calc R 1 H
H17C 0.1447 -0.1341 0.0574 0.206 Uiso calc R 1 H
C18 -0.3919(2) 0.1823(3) 0.1415(2) 0.0981(7) Uani d . 1 C
H18A -0.4638 0.1373 0.0842 0.147 Uiso calc R 1 H
H18B -0.3671 0.2719 0.1265 0.147 Uiso calc R 1 H
H18C -0.4321 0.1832 0.2037 0.147 Uiso calc R 1 H
C19 0.31455(16) 0.35585(15) 0.46904(11) 0.0463(4) Uani d . 1 C
C20 0.27000(19) 0.48123(16) 0.47074(12) 0.0571(4) Uani d . 1 C
H20 0.2824 0.5338 0.4171 0.069 Uiso calc R 1 H
C21 0.2071(2) 0.53068(17) 0.55083(13) 0.0617(5) Uani d . 1 C
C22 0.1915(2) 0.44959(18) 0.62950(13) 0.0646(5) Uani d . 1 C
H22 0.1497 0.4799 0.6845 0.077 Uiso calc R 1 H
C23 0.23694(19) 0.32523(18) 0.62706(13) 0.0618(5) Uani d . 1 C
H23 0.2258 0.2733 0.6813 0.074 Uiso calc R 1 H
C24 0.29906(17) 0.27329(16) 0.54692(12) 0.0515(4) Uani d . 1 C
C25 0.3439(2) 0.13495(18) 0.54331(15) 0.0744(5) Uani d . 1 C
H25 0.3846 0.1203 0.4803 0.089 Uiso calc R 1 H
C26 0.2108(4) 0.0339(2) 0.5351(3) 0.1514(13) Uani d . 1 C
H26A 0.2414 -0.0539 0.5331 0.227 Uiso calc R 1 H
H26B 0.1406 0.0428 0.4725 0.227 Uiso calc R 1 H
H26C 0.1660 0.0488 0.5945 0.227 Uiso calc R 1 H
C27 0.4614(4) 0.1144(4) 0.6354(2) 0.1447(12) Uani d . 1 C
H27A 0.4857 0.0246 0.6300 0.217 Uiso calc R 1 H
H27B 0.4254 0.1310 0.6985 0.217 Uiso calc R 1 H
H27C 0.5481 0.1746 0.6366 0.217 Uiso calc R 1 H
C28 0.1605(3) 0.6685(2) 0.55236(17) 0.0930(7) Uani d . 1 C
H28A 0.2314 0.7265 0.6026 0.140 Uiso calc R 1 H
H28B 0.0652 0.6672 0.5710 0.140 Uiso calc R 1 H
H28C 0.1552 0.7000 0.4845 0.140 Uiso calc R 1 H
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_publ_flag
C6 C1 C2 119.34(13) ?
C6 C1 C7 119.97(14) ?
C2 C1 C7 120.69(14) ?
C3 C2 C1 120.04(14) ?
C3 C2 C8 119.94(14) ?
C1 C2 C8 120.01(13) ?
C4 C3 C2 119.94(14) ?
C4 C3 H3 120.0 ?
C2 C3 H3 120.0 ?
O1 C4 C3 125.06(14) ?
O1 C4 C5 115.02(14) ?
C3 C4 C5 119.92(13) ?
C6 C5 O2 120.02(13) ?
C6 C5 C4 120.46(14) ?
O2 C5 C4 119.38(13) ?
C5 C6 C1 120.23(14) ?
C5 C6 H6 119.9 ?
C1 C6 H6 119.9 ?
N7 C7 C1 179.4(2) ?
C4 O1 C9 120.76(12) yes
C5 O2 C19 116.65(13) yes
N8 C8 C2 178.7(2) ?
C10 C9 C14 123.08(15) ?
C10 C9 O1 119.09(16) ?
C14 C9 O1 117.52(15) ?
C9 C10 C11 120.69(18) ?
C9 C10 H10 119.7 ?
C11 C10 H10 119.7 ?
C12 C11 C10 117.17(18) ?
C12 C11 C18 122.20(18) ?
C10 C11 C18 120.6(2) ?
C13 C12 C11 121.61(17) ?
C13 C12 H12 119.2 ?
C11 C12 H12 119.2 ?
C12 C13 C14 122.14(18) ?
C12 C13 H13 118.9 ?
C14 C13 H13 118.9 ?
C9 C14 C13 115.31(17) ?
C9 C14 C15 121.95(15) ?
C13 C14 C15 122.73(18) ?
C16 C15 C14 113.88(17) ?
C16 C15 C17 111.6(2) ?
C14 C15 C17 110.41(17) ?
C16 C15 H15 106.9 ?
C14 C15 H15 106.9 ?
C17 C15 H15 106.9 ?
C15 C16 H16A 109.5 ?
C15 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
C15 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
C15 C17 H17A 109.5 ?
C15 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
C15 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
C11 C18 H18A 109.5 ?
C11 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
C11 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
C20 C19 C24 121.91(15) ?
C20 C19 O2 121.01(13) ?
C24 C19 O2 117.03(15) ?
C19 C20 C21 121.19(15) ?
C19 C20 H20 119.4 ?
C21 C20 H20 119.4 ?
C20 C21 C22 117.59(18) ?
C20 C21 C28 120.63(16) ?
C22 C21 C28 121.77(18) ?
C23 C22 C21 120.59(17) ?
C23 C22 H22 119.7 ?
C21 C22 H22 119.7 ?
C22 C23 C24 122.73(15) ?
C22 C23 H23 118.6 ?
C24 C23 H23 118.6 ?
C19 C24 C23 115.99(17) ?
C19 C24 C25 121.78(16) ?
C23 C24 C25 122.22(15) ?
C24 C25 C27 112.6(2) ?
C24 C25 C26 110.5(2) ?
C27 C25 C26 110.3(2) ?
C24 C25 H25 107.8 ?
C27 C25 H25 107.8 ?
C26 C25 H25 107.8 ?
C25 C26 H26A 109.5 ?
C25 C26 H26B 109.5 ?
H26A C26 H26B 109.5 ?
C25 C26 H26C 109.5 ?
H26A C26 H26C 109.5 ?
H26B C26 H26C 109.5 ?
C25 C27 H27A 109.5 ?
C25 C27 H27B 109.5 ?
H27A C27 H27B 109.5 ?
C25 C27 H27C 109.5 ?
H27A C27 H27C 109.5 ?
H27B C27 H27C 109.5 ?
C21 C28 H28A 109.5 ?
C21 C28 H28B 109.5 ?
H28A C28 H28B 109.5 ?
C21 C28 H28C 109.5 ?
H28A C28 H28C 109.5 ?
H28B C28 H28C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 1.386(2) ?
C1 C2 1.402(2) ?
C1 C7 1.433(2) ?
C2 C3 1.384(2) ?
C2 C8 1.432(2) ?
C3 C4 1.381(2) ?
C3 H3 0.9300 ?
C4 O1 1.3579(19) yes
C4 C5 1.389(2) ?
C5 C6 1.373(2) ?
C5 O2 1.374(2) yes
C6 H6 0.9300 ?
N7 C7 1.136(2) yes
N8 C8 1.136(2) yes
O1 C9 1.406(2) ?
O2 C19 1.400(2) ?
C9 C10 1.374(3) ?
C9 C14 1.379(3) ?
C10 C11 1.386(3) ?
C10 H10 0.9300 ?
C11 C12 1.374(3) ?
C11 C18 1.498(3) ?
C12 C13 1.372(3) ?
C12 H12 0.9300 ?
C13 C14 1.394(2) ?
C13 H13 0.9300 ?
C14 C15 1.508(3) ?
C15 C16 1.503(3) ?
C15 C17 1.511(3) ?
C15 H15 0.9800 ?
C16 H16A 0.9600 ?
C16 H16B 0.9600 ?
C16 H16C 0.9600 ?
C17 H17A 0.9600 ?
C17 H17B 0.9600 ?
C17 H17C 0.9600 ?
C18 H18A 0.9600 ?
C18 H18B 0.9600 ?
C18 H18C 0.9600 ?
C19 C20 1.374(3) ?
C19 C24 1.385(2) ?
C20 C21 1.383(3) ?
C20 H20 0.9300 ?
C21 C22 1.384(3) ?
C21 C28 1.501(3) ?
C22 C23 1.367(3) ?
C22 H22 0.9300 ?
C23 C24 1.388(3) ?
C23 H23 0.9300 ?
C24 C25 1.501(3) ?
C25 C27 1.503(3) ?
C25 C26 1.512(4) ?
C25 H25 0.9800 ?
C26 H26A 0.9600 ?
C26 H26B 0.9600 ?
C26 H26C 0.9600 ?
C27 H27A 0.9600 ?
C27 H27B 0.9600 ?
C27 H27C 0.9600 ?
C28 H28A 0.9600 ?
C28 H28B 0.9600 ?
C28 H28C 0.9600 ?
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
C6 H6 Cg3 2_666 0.93 2.784 3.705(4) 171
C17 H17C Cg2 2_555 0.96 3.21 3.818(5) 122
C26 H26C Cg2 2_556 0.96 3.31 4.143(4) 146
C28 H28B Cg3 2_566 0.96 3.06 3.793(5) 134
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21131125
