#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/89/2018948.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_2018948
loop_
_publ_author_name
'Bats, Jan W.'
'Schell, Peter'
'Engels, Joachim W.'
_publ_section_title
;
 Biphenyl- and phenylnaphthalenyl-substituted
 1H-imidazole-4,5-dicarbonitrile catalysts for the coupling
 reaction of nucleoside methyl phosphonamidites
;
_journal_coeditor_code           EG3118
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              529
_journal_page_last               533
_journal_paper_doi               10.1107/S0108270113009293
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C23 H16 N4'
_chemical_formula_moiety         'C23 H16 N4'
_chemical_formula_sum            'C23 H16 N4'
_chemical_formula_weight         348.40
_chemical_melting_point          514.0(10)
_chemical_name_systematic
2-[8-(3,5-Dimethylphenyl)naphthalen-1-yl]-1H-imidazole-4,5-dicarbonitrile
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.7042(14)
_cell_length_b                   7.1632(7)
_cell_length_c                   15.0528(11)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      62
_cell_measurement_theta_min      46
_cell_volume                     1801.2(3)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0092
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3815
_diffrn_reflns_theta_full        69.89
_diffrn_reflns_theta_max         69.89
_diffrn_reflns_theta_min         5.30
_diffrn_standards_decay_%        2.0
_diffrn_standards_interval_time  90
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_T_max  0.857
_exptl_absorpt_correction_T_min  0.776
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'MolEN (Fair, 1990)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.122
_refine_ls_extinction_coef       0.0137(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         1781
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0268
_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)+(0.046P)²+0.15P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0703
_reflns_number_gt                1753
_reflns_number_total             1781
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            eg3118.cif
_cod_data_source_block           III
_cod_database_code               2018948
_cod_database_fobs_code          2018948
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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
_atom_site_symmetry_multiplicity
N N1 0.39034(9) 0.03608(19) 0.39285(9) 0.0420(3) Uani d . 1 1
N N2 0.48444(8) 0.0795(2) 0.49401(9) 0.0394(3) Uani d . 1 1
N N3 0.47805(12) 0.0167(3) 0.18351(11) 0.0665(5) Uani d . 1 1
N N4 0.66997(11) 0.1656(3) 0.38986(14) 0.0759(6) Uani d . 1 1
C C1 0.33666(9) 0.1751(2) 0.62080(10) 0.0393(3) Uani d . 1 1
C C2 0.37449(10) 0.3547(2) 0.62529(11) 0.0432(4) Uani d . 1 1
C C3 0.36311(12) 0.4641(3) 0.70001(13) 0.0534(4) Uani d . 1 1
H H3A 0.3887 0.5791 0.7032 0.064 Uiso calc R 1 1
C C4 0.31469(13) 0.4082(3) 0.77064(14) 0.0593(5) Uani d . 1 1
H H4A 0.3093 0.4842 0.8204 0.071 Uiso calc R 1 1
C C5 0.27531(11) 0.2422(3) 0.76655(13) 0.0550(5) Uani d . 1 1
H H5A 0.2421 0.2062 0.8130 0.066 Uiso calc R 1 1
C C6 0.28460(10) 0.1244(3) 0.69229(12) 0.0456(4) Uani d . 1 1
C C7 0.24059(12) -0.0446(3) 0.68892(15) 0.0551(5) Uani d . 1 1
H H7A 0.2076 -0.0769 0.7362 0.066 Uiso calc R 1 1
C C8 0.24593(14) -0.1599(3) 0.61781(15) 0.0605(5) Uani d . 1 1
H H8A 0.2144 -0.2667 0.6148 0.073 Uiso calc R 1 1
C C9 0.29923(11) -0.1173(3) 0.54884(13) 0.0516(4) Uani d . 1 1
H H9A 0.3033 -0.1982 0.5007 0.062 Uiso calc R 1 1
C C10 0.34525(10) 0.0400(2) 0.55056(11) 0.0409(3) Uani d . 1 1
C C11 0.42305(11) 0.4389(2) 0.55251(12) 0.0426(4) Uani d . 1 1
C C12 0.39158(11) 0.4619(2) 0.46758(12) 0.0438(4) Uani d . 1 1
H H12A 0.3397 0.4219 0.4557 0.053 Uiso calc R 1 1
C C13 0.43646(12) 0.5437(2) 0.40042(12) 0.0462(4) Uani d . 1 1
C C14 0.51353(12) 0.6051(2) 0.41944(13) 0.0501(4) Uani d . 1 1
H H14A 0.5440 0.6588 0.3745 0.060 Uiso calc R 1 1
C C15 0.54637(11) 0.5882(3) 0.50413(14) 0.0503(4) Uani d . 1 1
C C16 0.49942(13) 0.5053(3) 0.56997(13) 0.0486(4) Uani d . 1 1
H H16A 0.5200 0.4943 0.6272 0.058 Uiso calc R 1 1
C C17 0.40170(15) 0.5662(3) 0.30870(15) 0.0640(6) Uani d . 1 1
H H17A 0.3921 0.4454 0.2832 0.096 Uiso calc R 1 1
H H17B 0.4387 0.6340 0.2720 0.096 Uiso calc R 1 1
H H17C 0.3522 0.6337 0.3124 0.096 Uiso calc R 1 1
C C18 0.62974(14) 0.6562(4) 0.52483(18) 0.0712(6) Uani d . 1 1
H H18A 0.6681 0.5668 0.5037 0.107 Uiso calc R 1 1
H H18B 0.6355 0.6711 0.5879 0.107 Uiso calc R 1 1
H H18C 0.6386 0.7740 0.4960 0.107 Uiso calc R 1 1
C C19 0.40546(10) 0.0538(2) 0.47883(11) 0.0384(3) Uani d . 1 1
C C20 0.46288(11) 0.0564(2) 0.35248(10) 0.0414(4) Uani d . 1 1
C C21 0.52226(11) 0.0854(2) 0.41370(11) 0.0404(3) Uani d . 1 1
C C22 0.47209(12) 0.0383(3) 0.25815(12) 0.0486(4) Uani d . 1 1
C C23 0.60471(11) 0.1274(3) 0.40170(12) 0.0501(4) Uani d . 1 1
H H2A 0.5051(13) 0.085(3) 0.5428(16) 0.047(5) Uiso d . 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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
C19 N1 C20 104.82(14)
C19 N2 C21 107.84(14)
C19 N2 H2A 125.1(15)
C21 N2 H2A 127.0(15)
C6 C1 C2 117.37(14)
C6 C1 C10 116.25(15)
C2 C1 C10 126.37(14)
C3 C2 C1 119.04(16)
C3 C2 C11 116.30(16)
C1 C2 C11 124.59(15)
C2 C3 C4 122.47(18)
C2 C3 H3A 118.8
C4 C3 H3A 118.8
C5 C4 C3 119.78(18)
C5 C4 H4A 120.1
C3 C4 H4A 120.1
C4 C5 C6 120.41(18)
C4 C5 H5A 119.8
C6 C5 H5A 119.8
C5 C6 C7 118.87(17)
C5 C6 C1 120.78(16)
C7 C6 C1 120.35(16)
C8 C7 C6 120.99(18)
C8 C7 H7A 119.5
C6 C7 H7A 119.5
C7 C8 C9 119.63(18)
C7 C8 H8A 120.2
C9 C8 H8A 120.2
C10 C9 C8 121.58(18)
C10 C9 H9A 119.2
C8 C9 H9A 119.2
C9 C10 C1 120.84(16)
C9 C10 C19 115.11(15)
C1 C10 C19 123.98(14)
C16 C11 C12 118.75(16)
C16 C11 C2 120.00(16)
C12 C11 C2 121.15(16)
C13 C12 C11 120.98(17)
C13 C12 H12A 119.5
C11 C12 H12A 119.5
C12 C13 C14 118.92(17)
C12 C13 C17 120.30(17)
C14 C13 C17 120.77(17)
C13 C14 C15 121.71(17)
C13 C14 H14A 119.1
C15 C14 H14A 119.1
C14 C15 C16 117.73(17)
C14 C15 C18 121.65(19)
C16 C15 C18 120.62(19)
C11 C16 C15 121.86(18)
C11 C16 H16A 119.1
C15 C16 H16A 119.1
C13 C17 H17A 109.5
C13 C17 H17B 109.5
H17A C17 H17B 109.5
C13 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C15 C18 H18A 109.5
C15 C18 H18B 109.5
H18A C18 H18B 109.5
C15 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
N1 C19 N2 111.36(15)
N1 C19 C10 125.26(15)
N2 C19 C10 123.33(14)
N1 C20 C21 111.10(14)
N1 C20 C22 121.80(16)
C21 C20 C22 127.02(17)
N2 C21 C20 104.83(15)
N2 C21 C23 124.60(16)
C20 C21 C23 130.42(16)
N3 C22 C20 177.1(2)
N4 C23 C21 177.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C19 1.325(2)
N1 C20 1.363(2)
N2 C19 1.352(2)
N2 C21 1.365(2)
N2 H2A 0.81(2)
N3 C22 1.138(2)
N4 C23 1.138(3)
C1 C6 1.430(2)
C1 C2 1.435(2)
C1 C10 1.440(2)
C2 C3 1.384(3)
C2 C11 1.491(2)
C3 C4 1.394(3)
C3 H3A 0.9300
C4 C5 1.361(3)
C4 H4A 0.9300
C5 C6 1.409(3)
C5 H5A 0.9300
C6 C7 1.417(3)
C7 C8 1.355(3)
C7 H7A 0.9300
C8 C9 1.401(3)
C8 H8A 0.9300
C9 C10 1.365(3)
C9 H9A 0.9300
C10 C19 1.479(2)
C11 C16 1.387(3)
C11 C12 1.392(2)
C12 C13 1.388(2)
C12 H12A 0.9300
C13 C14 1.390(3)
C13 C17 1.506(3)
C14 C15 1.393(3)
C14 H14A 0.9300
C15 C16 1.397(3)
C15 C18 1.508(3)
C16 H16A 0.9300
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
C20 C21 1.370(2)
C20 C22 1.434(2)
C21 C23 1.421(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
N2 H2A N3 2_655 0.81(2) 2.26(2) 3.001(2) 152(2)
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
C6 C1 C2 C3 4.0(2)
C10 C1 C2 C3 -176.64(17)
C6 C1 C2 C11 -172.89(16)
C10 C1 C2 C11 6.5(3)
C1 C2 C3 C4 -1.5(3)
C11 C2 C3 C4 175.69(18)
C2 C3 C4 C5 -1.4(3)
C3 C4 C5 C6 1.5(3)
C4 C5 C6 C7 -177.90(19)
C4 C5 C6 C1 1.2(3)
C2 C1 C6 C5 -3.9(2)
C10 C1 C6 C5 176.62(16)
C2 C1 C6 C7 175.19(16)
C10 C1 C6 C7 -4.2(2)
C5 C6 C7 C8 178.2(2)
C1 C6 C7 C8 -0.9(3)
C6 C7 C8 C9 3.8(3)
C7 C8 C9 C10 -1.2(3)
C8 C9 C10 C1 -4.3(3)
C8 C9 C10 C19 172.79(18)
C6 C1 C10 C9 6.8(2)
C2 C1 C10 C9 -172.56(17)
C6 C1 C10 C19 -170.01(15)
C2 C1 C10 C19 10.6(3)
C3 C2 C11 C16 55.2(2)
C1 C2 C11 C16 -127.87(19)
C3 C2 C11 C12 -121.27(19)
C1 C2 C11 C12 55.7(2)
C16 C11 C12 C13 2.3(2)
C2 C11 C12 C13 178.74(15)
C11 C12 C13 C14 -0.9(2)
C11 C12 C13 C17 179.54(17)
C12 C13 C14 C15 -0.6(2)
C17 C13 C14 C15 178.99(17)
C13 C14 C15 C16 0.6(3)
C13 C14 C15 C18 -179.54(19)
C12 C11 C16 C15 -2.3(3)
C2 C11 C16 C15 -178.80(17)
C14 C15 C16 C11 0.9(3)
C18 C15 C16 C11 -178.97(19)
C20 N1 C19 N2 -1.6(2)
C20 N1 C19 C10 -179.23(14)
C21 N2 C19 N1 2.2(2)
C21 N2 C19 C10 179.93(14)
C9 C10 C19 N1 52.5(2)
C1 C10 C19 N1 -130.50(18)
C9 C10 C19 N2 -124.88(18)
C1 C10 C19 N2 52.1(2)
C19 N1 C20 C21 0.35(19)
C19 N1 C20 C22 177.34(16)
C19 N2 C21 C20 -1.85(17)
C19 N2 C21 C23 174.04(16)
N1 C20 C21 N2 0.94(18)
C22 C20 C21 N2 -175.85(18)
N1 C20 C21 C23 -174.61(17)
C22 C20 C21 C23 8.6(3)
