#------------------------------------------------------------------------------
#$Date: 2016-03-26 19:27:03 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180435 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/04/7210431.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_7210431
loop_
_publ_author_name
'Aakeröy, Christer B.'
'Epa, Kanishka N.'
'Forbes, Safiyyah'
'Desper, John'
_publ_section_title
;
 Competing hydrogen-bond donors: phenols vs. cyanooximes
;
_journal_issue                   30
_journal_name_full               CrystEngComm
_journal_page_first              5946
_journal_paper_doi               10.1039/c3ce41023d
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         '(C8 H6 N2 O2) (C15 H15 N3)'
_chemical_formula_sum            'C23 H21 N5 O2'
_chemical_formula_weight         399.45
_chemical_name_systematic
'KE14PCY20 4-HO-PhC(CN)=NOH, 1-[3-pyridylmethyl]-5,6-dimethylbenzimidazole'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.555(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.9863(9)
_cell_length_b                   11.4938(7)
_cell_length_c                   14.1061(9)
_cell_measurement_reflns_used    8295
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      32.40
_cell_measurement_theta_min      2.32
_cell_volume                     2028.4(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22683
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         32.57
_diffrn_reflns_theta_min         1.89
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9879
_exptl_absorpt_correction_T_min  0.9778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         6808
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0532
_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)+(0.0750P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1425
_refine_ls_wR_factor_ref         0.1558
_reflns_number_gt                5052
_reflns_number_total             6808
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce41023d.txt
_cod_data_source_block           PhOx:7
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7210431
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
N11 N -0.04232(8) 0.12115(9) 0.41997(7) 0.0238(2) Uani 1 1 d .
C12 C -0.13522(10) 0.06026(11) 0.39892(9) 0.0265(2) Uani 1 1 d .
H12 H -0.1953 0.0828 0.4210 0.032 Uiso 1 1 calc R
N13 N -0.13421(8) -0.03313(9) 0.34498(7) 0.0264(2) Uani 1 1 d .
C14 C -0.03278(9) -0.03364(10) 0.32930(8) 0.0232(2) Uani 1 1 d .
C15 C 0.01274(10) -0.11153(10) 0.27632(9) 0.0260(2) Uani 1 1 d .
H15 H -0.0273 -0.1757 0.2431 0.031 Uiso 1 1 calc R
C16 C 0.11689(10) -0.09398(11) 0.27289(9) 0.0263(2) Uani 1 1 d .
C17 C 0.17722(9) 0.00123(10) 0.32366(8) 0.0249(2) Uani 1 1 d .
C18 C 0.13146(9) 0.08043(10) 0.37479(8) 0.0240(2) Uani 1 1 d .
H18 H 0.1709 0.1450 0.4077 0.029 Uiso 1 1 calc R
C19 C 0.02597(9) 0.06209(10) 0.37618(8) 0.0220(2) Uani 1 1 d .
C20 C 0.16616(12) -0.17459(13) 0.21307(11) 0.0373(3) Uani 1 1 d .
H20A H 0.1144 -0.2349 0.1829 0.056 Uiso 1 1 calc R
H20B H 0.2300 -0.2111 0.2560 0.056 Uiso 1 1 calc R
H20C H 0.1862 -0.1302 0.1614 0.056 Uiso 1 1 calc R
C21 C 0.29103(10) 0.01755(12) 0.32070(10) 0.0323(3) Uani 1 1 d .
H21A H 0.3237 0.0804 0.3656 0.048 Uiso 1 1 calc R
H21B H 0.2927 0.0376 0.2536 0.048 Uiso 1 1 calc R
H21C H 0.3309 -0.0547 0.3409 0.048 Uiso 1 1 calc R
N31 N 0.09178(8) 0.49636(9) 0.39703(7) 0.0277(2) Uani 1 1 d .
C32 C 0.08167(9) 0.39541(11) 0.44161(8) 0.0248(2) Uani 1 1 d .
H32 H 0.1431 0.3637 0.4867 0.030 Uiso 1 1 calc R
C33 C -0.01358(9) 0.33529(10) 0.42518(8) 0.0215(2) Uani 1 1 d .
C34 C -0.10332(9) 0.38280(11) 0.35974(8) 0.0254(2) Uani 1 1 d .
H34 H -0.1705 0.3445 0.3472 0.031 Uiso 1 1 calc R
C35 C -0.09379(10) 0.48650(11) 0.31302(9) 0.0282(3) Uani 1 1 d .
H35 H -0.1540 0.5204 0.2678 0.034 Uiso 1 1 calc R
C36 C 0.00497(10) 0.53954(11) 0.33357(9) 0.0275(3) Uani 1 1 d .
H36 H 0.0115 0.6103 0.3009 0.033 Uiso 1 1 calc R
C37 C -0.01951(10) 0.22527(10) 0.48153(8) 0.0253(2) Uani 1 1 d .
H37A H 0.0494 0.2143 0.5319 0.030 Uiso 1 1 calc R
H37B H -0.0759 0.2344 0.5163 0.030 Uiso 1 1 calc R
C41 C 0.50310(9) 0.71951(10) 0.43446(8) 0.0222(2) Uani 1 1 d .
C42 C 0.54730(10) 0.62327(11) 0.39933(9) 0.0262(2) Uani 1 1 d .
H42 H 0.5147 0.5491 0.3980 0.031 Uiso 1 1 calc R
C43 C 0.63766(10) 0.63465(10) 0.36658(9) 0.0264(2) Uani 1 1 d .
H43 H 0.6672 0.5683 0.3434 0.032 Uiso 1 1 calc R
C44 C 0.68605(9) 0.74351(10) 0.36738(8) 0.0227(2) Uani 1 1 d .
O44 O 0.77344(7) 0.75104(8) 0.33248(6) 0.0282(2) Uani 1 1 d .
H44 H 0.7930(13) 0.8269(15) 0.3349(11) 0.034 Uiso 1 1 d .
C45 C 0.64366(10) 0.83943(10) 0.40382(9) 0.0254(2) Uani 1 1 d .
H45 H 0.6767 0.9135 0.4057 0.030 Uiso 1 1 calc R
C46 C 0.55357(10) 0.82707(10) 0.43729(9) 0.0248(2) Uani 1 1 d .
H46 H 0.5255 0.8929 0.4626 0.030 Uiso 1 1 calc R
C47 C 0.40589(9) 0.71007(10) 0.46784(8) 0.0237(2) Uani 1 1 d .
N47 N 0.33476(9) 0.63053(9) 0.43515(8) 0.0292(2) Uani 1 1 d .
O47 O 0.25141(8) 0.63869(9) 0.47802(7) 0.0341(2) Uani 1 1 d .
H47 H 0.2031(14) 0.5775(15) 0.4416(11) 0.041 Uiso 1 1 d .
C48 C 0.39068(10) 0.79494(11) 0.53931(9) 0.0265(2) Uani 1 1 d .
N48 N 0.38268(10) 0.86213(10) 0.59644(9) 0.0373(3) Uani 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
C12 N11 C19 106.70(10)
C12 N11 C37 125.38(10)
C19 N11 C37 127.85(10)
N13 C12 N11 113.61(11)
N13 C12 H12 123.2
N11 C12 H12 123.2
C12 N13 C14 104.56(10)
N13 C14 C15 129.97(11)
N13 C14 C19 109.91(10)
C15 C14 C19 120.13(11)
C16 C15 C14 118.99(11)
C16 C15 H15 120.5
C14 C15 H15 120.5
C15 C16 C17 120.47(11)
C15 C16 C20 119.79(12)
C17 C16 C20 119.73(12)
C18 C17 C16 120.71(11)
C18 C17 C21 119.58(11)
C16 C17 C21 119.70(11)
C17 C18 C19 117.88(11)
C17 C18 H18 121.1
C19 C18 H18 121.1
N11 C19 C18 132.99(11)
N11 C19 C14 105.22(10)
C18 C19 C14 121.76(11)
C16 C20 H20A 109.5
C16 C20 H20B 109.5
H20A C20 H20B 109.5
C16 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C17 C21 H21A 109.5
C17 C21 H21B 109.5
H21A C21 H21B 109.5
C17 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C36 N31 C32 117.69(10)
N31 C32 C33 123.33(11)
N31 C32 H32 118.3
C33 C32 H32 118.3
C32 C33 C34 117.95(11)
C32 C33 C37 120.10(10)
C34 C33 C37 121.86(10)
C35 C34 C33 119.26(11)
C35 C34 H34 120.4
C33 C34 H34 120.4
C36 C35 C34 118.54(11)
C36 C35 H35 120.7
C34 C35 H35 120.7
N31 C36 C35 123.23(11)
N31 C36 H36 118.4
C35 C36 H36 118.4
N11 C37 C33 113.87(9)
N11 C37 H37A 108.8
C33 C37 H37A 108.8
N11 C37 H37B 108.8
C33 C37 H37B 108.8
H37A C37 H37B 107.7
C46 C41 C42 118.51(11)
C46 C41 C47 119.69(10)
C42 C41 C47 121.80(10)
C43 C42 C41 120.78(11)
C43 C42 H42 119.6
C41 C42 H42 119.6
C42 C43 C44 120.22(11)
C42 C43 H43 119.9
C44 C43 H43 119.9
O44 C44 C45 122.44(10)
O44 C44 C43 118.17(11)
C45 C44 C43 119.38(11)
C44 O44 H44 107.6(10)
C46 C45 C44 120.01(11)
C46 C45 H45 120.0
C44 C45 H45 120.0
C45 C46 C41 121.06(11)
C45 C46 H46 119.5
C41 C46 H46 119.5
N47 C47 C48 120.31(11)
N47 C47 C41 122.16(10)
C48 C47 C41 117.53(10)
C47 N47 O47 111.44(10)
N47 O47 H47 100.8(10)
N48 C48 C47 177.50(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N11 C12 1.3569(15)
N11 C19 1.3867(15)
N11 C37 1.4615(15)
C12 N13 1.3179(16)
C12 H12 0.9500
N13 C14 1.3929(15)
C14 C15 1.3951(17)
C14 C19 1.3999(16)
C15 C16 1.3812(18)
C15 H15 0.9500
C16 C17 1.4224(17)
C16 C20 1.5064(18)
C17 C18 1.3900(17)
C17 C21 1.5014(17)
C18 C19 1.3913(16)
C18 H18 0.9500
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 0.9800
N31 C36 1.3333(16)
N31 C32 1.3428(16)
C32 C33 1.3811(16)
C32 H32 0.9500
C33 C34 1.3897(16)
C33 C37 1.5066(16)
C34 C35 1.3835(17)
C34 H34 0.9500
C35 C36 1.3788(18)
C35 H35 0.9500
C36 H36 0.9500
C37 H37A 0.9900
C37 H37B 0.9900
C41 C46 1.3948(16)
C41 C42 1.3968(17)
C41 C47 1.4649(16)
C42 C43 1.3778(17)
C42 H42 0.9500
C43 C44 1.3988(16)
C43 H43 0.9500
C44 O44 1.3557(14)
C44 C45 1.3908(17)
O44 H44 0.907(17)
C45 C46 1.3815(17)
C45 H45 0.9500
C46 H46 0.9500
C47 N47 1.2934(15)
C47 C48 1.4538(17)
N47 O47 1.3774(14)
O47 H47 0.990(18)
C48 N48 1.1408(16)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O47 H47 N31 0.990(18) 1.693(18) 2.6474(14) 160.7(15) .
O44 H44 N13 0.907(17) 1.852(17) 2.7405(14) 166.1(15) 1_665
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
C19 N11 C12 N13 -0.25(13)
C37 N11 C12 N13 -177.38(10)
N11 C12 N13 C14 -0.04(13)
C12 N13 C14 C15 -179.30(12)
C12 N13 C14 C19 0.31(12)
N13 C14 C15 C16 -179.00(11)
C19 C14 C15 C16 1.43(16)
C14 C15 C16 C17 0.80(17)
C14 C15 C16 C20 -177.79(11)
C15 C16 C17 C18 -2.18(17)
C20 C16 C17 C18 176.40(11)
C15 C16 C17 C21 178.80(11)
C20 C16 C17 C21 -2.61(17)
C16 C17 C18 C19 1.25(16)
C21 C17 C18 C19 -179.73(10)
C12 N11 C19 C18 -177.74(12)
C37 N11 C19 C18 -0.7(2)
C12 N11 C19 C14 0.42(12)
C37 N11 C19 C14 177.46(10)
C17 C18 C19 N11 178.91(11)
C17 C18 C19 C14 1.01(16)
N13 C14 C19 N11 -0.46(12)
C15 C14 C19 N11 179.20(10)
N13 C14 C19 C18 177.95(10)
C15 C14 C19 C18 -2.39(16)
C36 N31 C32 C33 -0.29(18)
N31 C32 C33 C34 -0.58(18)
N31 C32 C33 C37 -177.24(11)
C32 C33 C34 C35 0.85(17)
C37 C33 C34 C35 177.45(11)
C33 C34 C35 C36 -0.29(18)
C32 N31 C36 C35 0.90(18)
C34 C35 C36 N31 -0.62(19)
C12 N11 C37 C33 -109.70(13)
C19 N11 C37 C33 73.78(14)
C32 C33 C37 N11 -115.14(12)
C34 C33 C37 N11 68.33(14)
C46 C41 C42 C43 -1.12(17)
C47 C41 C42 C43 178.76(11)
C41 C42 C43 C44 -0.51(18)
C42 C43 C44 O44 -178.59(11)
C42 C43 C44 C45 1.60(18)
O44 C44 C45 C46 179.15(10)
C43 C44 C45 C46 -1.05(17)
C44 C45 C46 C41 -0.60(17)
C42 C41 C46 C45 1.68(17)
C47 C41 C46 C45 -178.21(10)
C46 C41 C47 N47 153.50(12)
C42 C41 C47 N47 -26.38(17)
C46 C41 C47 C48 -25.85(15)
C42 C41 C47 C48 154.27(11)
C48 C47 N47 O47 -1.26(16)
C41 C47 N47 O47 179.41(10)
