# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_new
_database_code_depnum_ccdc_archive 'CCDC 1483389'
_audit_update_record             
;
2016-06-03 deposited with the CCDC.
2018-02-12 downloaded from the CCDC.
;

_audit_creation_date             2013-04-30T10:22:49-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_sum            'C13 H15 N3 O'
_chemical_formula_moiety         'C13 H15 N3 O'
_chemical_formula_weight         229.28

#------------------ UNIT CELL INFORMATION -----------------------------------#
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc '
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'

_cell_length_a                   10.4959(3)
_cell_length_b                   9.9047(3)
_cell_length_c                   23.1897(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.365(2)
_cell_angle_gamma                90
_cell_volume                     2313.10(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4110
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      27.68

#------------------ CRYSTAL INFORMATION -------------------------------------#
_exptl_crystal_description       cuboid
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9654
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   
;
SADABS (Bruker, 2004)
;

#------------------ DATA COLLECTION INFORMATION -----------------------------#
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Bruker X8 ApexII 4K Kappa CCD
;
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean 512
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0

_diffrn_reflns_number            23821
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_full        27.99
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_reflns_number_total             5567
_reflns_number_gt                4024
_reflns_threshold_expression     >2σ(I)
_exptl_special_details           
;
The intensity data was collected on a Bruker X8 Apex II 4K Kappa CCD
diffractometer using an exposure time of 40 seconds/frame. A total of 1160
frames were collected with a frame width of 0.5° covering up 
to θ = 28.0° with 99.8% completeness accomplished
;


#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'Saint-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND 3.0c (Brandenburg & Putz, 2004)'
_computing_publication_material  'WingGX (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0458P)²+0.6335P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5567
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_ref         0.1123
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.252

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C2 C 0.21902(15) 0.52504(15) 0.12779(6) 0.0213(3) Uani 1 d . . .
H2C H 0.1552 0.5867 0.1006 0.026 Uiso 1 calc R . .
H2D H 0.2984 0.578 0.149 0.026 Uiso 1 calc R . .
C3 C 0.15560(15) 0.46359(15) 0.17341(6) 0.0211(3) Uani 1 d . . .
H3A H 0.0822 0.4032 0.1522 0.025 Uiso 1 calc R . .
H3B H 0.2225 0.4081 0.2023 0.025 Uiso 1 calc R . .
C5 C 0.62078(15) 0.47909(15) 0.10339(6) 0.0204(3) Uani 1 d . . .
H5A H 0.5242 0.4639 0.0866 0.024 Uiso 1 calc R . .
H5B H 0.639 0.5757 0.098 0.024 Uiso 1 calc R . .
C6 C 0.66230(16) 0.44477(15) 0.17008(6) 0.0240(3) Uani 1 d . . .
H6A H 0.6338 0.3515 0.1756 0.029 Uiso 1 calc R . .
H6B H 0.7603 0.4484 0.1855 0.029 Uiso 1 calc R . .
C31 C 0.10256(14) 0.56815(14) 0.20721(6) 0.0183(3) Uani 1 d . . .
C33 C -0.01528(15) 0.64955(15) 0.26125(6) 0.0225(3) Uani 1 d . . .
H33 H -0.0753 0.6571 0.285 0.027 Uiso 1 calc R . .
C35 C 0.12644(15) 0.70371(15) 0.21199(6) 0.0207(3) Uani 1 d . . .
H35 H 0.184 0.7533 0.1947 0.025 Uiso 1 calc R . .
C61 C 0.60288(15) 0.54020(15) 0.20556(6) 0.0195(3) Uani 1 d . . .
C63 C 0.48858(16) 0.60772(15) 0.26385(6) 0.0227(3) Uani 1 d . . .
H63 H 0.434 0.6083 0.2903 0.027 Uiso 1 calc R . .
C65 C 0.61026(16) 0.67768(15) 0.20789(6) 0.0231(3) Uani 1 d . . .
H65 H 0.657 0.7338 0.1875 0.028 Uiso 1 calc R . .
C141 C 0.28907(18) -0.01797(17) -0.11558(7) 0.0299(4) Uani 1 d . . .
H14A H 0.3827 -0.045 -0.1029 0.045 Uiso 1 calc R . .
H14B H 0.2654 0.0123 -0.1575 0.045 Uiso 1 calc R . .
H14C H 0.2334 -0.0951 -0.1119 0.045 Uiso 1 calc R . .
C441 C 0.86744(17) -0.00737(16) -0.11800(7) 0.0265(4) Uani 1 d . . .
H44A H 0.9549 0.0256 -0.1188 0.04 Uiso 1 calc R . .
H44B H 0.8093 -0.0143 -0.1592 0.04 Uiso 1 calc R . .
H44C H 0.8769 -0.0965 -0.0989 0.04 Uiso 1 calc R . .
N32 N 0.01295(13) 0.53440(12) 0.23863(5) 0.0228(3) Uani 1 d . . .
N34 N 0.05071(13) 0.75443(13) 0.24675(5) 0.0204(3) Uani 1 d . . .
N62 N 0.52536(13) 0.49625(12) 0.24111(5) 0.0224(3) Uani 1 d . . .
N64 N 0.53727(13) 0.71946(13) 0.24527(5) 0.0210(3) Uani 1 d . . .
H1 H 0.355(2) 0.270(2) 0.0991(9) 0.055(6) Uiso 1 d . . .
H34 H 0.0370(19) 0.847(2) 0.2543(8) 0.047(6) Uiso 1 d . . .
H64 H 0.517(2) 0.810(2) 0.2523(9) 0.055(6) Uiso 1 d . . .
H2 H 0.846(2) 0.337(2) 0.0735(9) 0.059(6) Uiso 1 d . . .
C1 C 0.19735(15) 0.41178(15) 0.03646(6) 0.0204(3) Uani 1 d . . .
H1A H 0.1341 0.4795 0.019 0.024 Uiso 1 calc R . .
C11 C 0.22353(14) 0.30492(15) -0.00156(6) 0.0193(3) Uani 1 d . . .
C12 C 0.31415(14) 0.20076(15) 0.02221(6) 0.0196(3) Uani 1 d . . .
C13 C 0.33403(15) 0.09745(15) -0.01507(6) 0.0223(3) Uani 1 d . . .
H13 H 0.3944 0.0267 0.0015 0.027 Uiso 1 calc R . .
C14 C 0.26713(15) 0.09598(15) -0.07605(6) 0.0226(3) Uani 1 d . . .
C15 C 0.17861(15) 0.20038(16) -0.09991(6) 0.0237(3) Uani 1 d . . .
H15 H 0.1332 0.2013 -0.1416 0.028 Uiso 1 calc R . .
C16 C 0.15663(15) 0.30250(16) -0.06317(6) 0.0230(3) Uani 1 d . . .
H16 H 0.0952 0.3722 -0.0799 0.028 Uiso 1 calc R . .
N1 N 0.25700(12) 0.41759(12) 0.09283(5) 0.0210(3) Uani 1 d . . .
O1 O 0.38387(11) 0.19851(11) 0.08119(4) 0.0245(3) Uani 1 d . . .
C4 C 0.62735(15) 0.34200(14) 0.02125(6) 0.0200(3) Uani 1 d . . .
H4 H 0.5342 0.3565 0.0073 0.024 Uiso 1 calc R . .
C41 C 0.69088(15) 0.25923(14) -0.01451(6) 0.0189(3) Uani 1 d . . .
C42 C 0.82790(15) 0.23010(15) 0.00489(6) 0.0198(3) Uani 1 d . . .
C43 C 0.88453(15) 0.14562(15) -0.02924(6) 0.0212(3) Uani 1 d . . .
H43 H 0.9768 0.126 -0.0158 0.025 Uiso 1 calc R . .
C44 C 0.80763(16) 0.08981(14) -0.08270(6) 0.0213(3) Uani 1 d . . .
C45 C 0.67246(15) 0.12219(15) -0.10314(6) 0.0224(3) Uani 1 d . . .
H45 H 0.6197 0.0871 -0.1403 0.027 Uiso 1 calc R . .
C46 C 0.61570(16) 0.20511(15) -0.06924(6) 0.0217(3) Uani 1 d . . .
H46 H 0.5238 0.2258 -0.0834 0.026 Uiso 1 calc R . .
N2 N 0.69278(12) 0.39604(12) 0.07097(5) 0.0207(3) Uani 1 d . . .
O2 O 0.90683(11) 0.28304(11) 0.05705(4) 0.0247(3) Uani 1 d . . .



#------------------ MOLECULAR GEOMETRY --------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag


C2 N1 1.4597(17) . ?
C2 C3 1.5262(19) . ?
C2 H2C 0.99 . ?
C2 H2D 0.99 . ?
C3 C31 1.4977(19) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C5 N2 1.4604(17) . ?
C5 C6 1.5225(19) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 C61 1.4995(19) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C31 C35 1.365(2) . ?
C31 N32 1.3831(18) . ?
C33 N32 1.3234(18) . ?
C33 N34 1.3428(19) . ?
C33 H33 0.95 . ?
C35 N34 1.3766(18) . ?
C35 H35 0.95 . ?
C61 C65 1.364(2) . ?
C61 N62 1.3816(18) . ?
C63 N62 1.3270(18) . ?
C63 N64 1.3400(19) . ?
C63 H63 0.95 . ?
C65 N64 1.3726(18) . ?
C65 H65 0.95 . ?
C141 C14 1.512(2) . ?
C141 H14A 0.98 . ?
C141 H14B 0.98 . ?
C141 H14C 0.98 . ?
C441 C44 1.5101(19) . ?
C441 H44A 0.98 . ?
C441 H44B 0.98 . ?
C441 H44C 0.98 . ?
N34 H34 0.95(2) . ?
N64 H64 0.94(2) . ?
C1 N1 1.2819(18) . ?
C1 C11 1.452(2) . ?
C1 H1A 0.95 . ?
C11 C16 1.4034(19) . ?
C11 C12 1.406(2) . ?
C12 O1 1.3574(16) . ?
C12 C13 1.393(2) . ?
C13 C14 1.390(2) . ?
C13 H13 0.95 . ?
C14 C15 1.396(2) . ?
C15 C16 1.383(2) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
O1 H1 0.91(2) . ?
C4 N2 1.2812(18) . ?
C4 C41 1.4547(19) . ?
C4 H4 0.95 . ?
C41 C46 1.3988(19) . ?
C41 C42 1.410(2) . ?
C42 O2 1.3638(17) . ?
C42 C43 1.395(2) . ?
C43 C44 1.389(2) . ?
C43 H43 0.95 . ?
C44 C45 1.401(2) . ?
C45 C46 1.382(2) . ?
C45 H45 0.95 . ?
C46 H46 0.95 . ?
O2 H2 0.99(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag


N1 C2 C3 109.56(12) . . ?
N1 C2 H2C 109.8 . . ?
C3 C2 H2C 109.8 . . ?
N1 C2 H2D 109.8 . . ?
C3 C2 H2D 109.8 . . ?
H2C C2 H2D 108.2 . . ?
C31 C3 C2 112.71(12) . . ?
C31 C3 H3A 109 . . ?
C2 C3 H3A 109 . . ?
C31 C3 H3B 109 . . ?
C2 C3 H3B 109 . . ?
H3A C3 H3B 107.8 . . ?
N2 C5 C6 110.83(12) . . ?
N2 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
N2 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C61 C6 C5 111.87(12) . . ?
C61 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C61 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C35 C31 N32 109.37(12) . . ?
C35 C31 C3 129.49(13) . . ?
N32 C31 C3 121.12(13) . . ?
N32 C33 N34 112.24(12) . . ?
N32 C33 H33 123.9 . . ?
N34 C33 H33 123.9 . . ?
C31 C35 N34 106.47(13) . . ?
C31 C35 H35 126.8 . . ?
N34 C35 H35 126.8 . . ?
C65 C61 N62 109.11(13) . . ?
C65 C61 C6 128.55(13) . . ?
N62 C61 C6 122.32(13) . . ?
N62 C63 N64 112.30(13) . . ?
N62 C63 H63 123.9 . . ?
N64 C63 H63 123.9 . . ?
C61 C65 N64 106.88(13) . . ?
C61 C65 H65 126.6 . . ?
N64 C65 H65 126.6 . . ?
C14 C141 H14A 109.5 . . ?
C14 C141 H14B 109.5 . . ?
H14A C141 H14B 109.5 . . ?
C14 C141 H14C 109.5 . . ?
H14A C141 H14C 109.5 . . ?
H14B C141 H14C 109.5 . . ?
C44 C441 H44A 109.5 . . ?
C44 C441 H44B 109.5 . . ?
H44A C441 H44B 109.5 . . ?
C44 C441 H44C 109.5 . . ?
H44A C441 H44C 109.5 . . ?
H44B C441 H44C 109.5 . . ?
C33 N32 C31 105.19(12) . . ?
C33 N34 C35 106.74(12) . . ?
C33 N34 H34 125.7(12) . . ?
C35 N34 H34 127.0(12) . . ?
C63 N62 C61 105.13(12) . . ?
C63 N64 C65 106.58(12) . . ?
C63 N64 H64 127.2(13) . . ?
C65 N64 H64 125.8(13) . . ?
N1 C1 C11 122.02(14) . . ?
N1 C1 H1A 119 . . ?
C11 C1 H1A 119 . . ?
C16 C11 C12 118.40(13) . . ?
C16 C11 C1 120.30(13) . . ?
C12 C11 C1 121.29(13) . . ?
O1 C12 C13 118.74(13) . . ?
O1 C12 C11 121.34(13) . . ?
C13 C12 C11 119.92(13) . . ?
C14 C13 C12 121.20(14) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 118.96(14) . . ?
C13 C14 C141 120.32(14) . . ?
C15 C14 C141 120.71(13) . . ?
C16 C15 C14 120.36(13) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C11 121.15(14) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
C1 N1 C2 117.89(13) . . ?
C12 O1 H1 107.0(12) . . ?
N2 C4 C41 122.20(14) . . ?
N2 C4 H4 118.9 . . ?
C41 C4 H4 118.9 . . ?
C46 C41 C42 118.35(13) . . ?
C46 C41 C4 120.08(13) . . ?
C42 C41 C4 121.56(13) . . ?
O2 C42 C43 118.98(13) . . ?
O2 C42 C41 120.95(13) . . ?
C43 C42 C41 120.07(13) . . ?
C44 C43 C42 120.78(14) . . ?
C44 C43 H43 119.6 . . ?
C42 C43 H43 119.6 . . ?
C43 C44 C45 119.30(13) . . ?
C43 C44 C441 120.77(14) . . ?
C45 C44 C441 119.91(13) . . ?
C46 C45 C44 120.09(13) . . ?
C46 C45 H45 120 . . ?
C44 C45 H45 120 . . ?
C45 C46 C41 121.36(14) . . ?
C45 C46 H46 119.3 . . ?
C41 C46 H46 119.3 . . ?
C4 N2 C5 118.33(13) . . ?
C42 O2 H2 104.6(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C31 -174.72(12) . . . . ?
N2 C5 C6 C61 172.80(12) . . . . ?
C2 C3 C31 C35 -15.0(2) . . . . ?
C2 C3 C31 N32 163.19(13) . . . . ?
N32 C31 C35 N34 -0.01(16) . . . . ?
C3 C31 C35 N34 178.33(14) . . . . ?
C5 C6 C61 C65 -54.8(2) . . . . ?
C5 C6 C61 N62 123.18(15) . . . . ?
N62 C61 C65 N64 0.21(17) . . . . ?
C6 C61 C65 N64 178.43(14) . . . . ?
N34 C33 N32 C31 -0.36(17) . . . . ?
C35 C31 N32 C33 0.22(16) . . . . ?
C3 C31 N32 C33 -178.28(13) . . . . ?
N32 C33 N34 C35 0.36(17) . . . . ?
C31 C35 N34 C33 -0.20(16) . . . . ?
N64 C63 N62 C61 -0.01(17) . . . . ?
C65 C61 N62 C63 -0.12(16) . . . . ?
C6 C61 N62 C63 -178.48(13) . . . . ?
N62 C63 N64 C65 0.14(17) . . . . ?
C61 C65 N64 C63 -0.21(16) . . . . ?
N1 C1 C11 C16 -179.67(14) . . . . ?
N1 C1 C11 C12 1.3(2) . . . . ?
C16 C11 C12 O1 178.78(13) . . . . ?
C1 C11 C12 O1 -2.2(2) . . . . ?
C16 C11 C12 C13 -1.0(2) . . . . ?
C1 C11 C12 C13 178.01(13) . . . . ?
O1 C12 C13 C14 -178.81(13) . . . . ?
C11 C12 C13 C14 1.0(2) . . . . ?
C12 C13 C14 C15 0.0(2) . . . . ?
C12 C13 C14 C141 -179.33(14) . . . . ?
C13 C14 C15 C16 -0.9(2) . . . . ?
C141 C14 C15 C16 178.41(14) . . . . ?
C14 C15 C16 C11 0.9(2) . . . . ?
C12 C11 C16 C15 0.1(2) . . . . ?
C1 C11 C16 C15 -178.93(14) . . . . ?
C11 C1 N1 N1 0.00(8) . . . 1 ?
C11 C1 N1 C2 -176.99(13) . . . . ?
C3 C2 N1 N1 0.00(8) . . . 1 ?
C3 C2 N1 C1 114.80(14) . . . . ?
N2 C4 C41 C46 -178.43(14) . . . . ?
N2 C4 C41 C42 2.3(2) . . . . ?
C46 C41 C42 O2 178.21(13) . . . . ?
C4 C41 C42 O2 -2.5(2) . . . . ?
C46 C41 C42 C43 -2.1(2) . . . . ?
C4 C41 C42 C43 177.22(13) . . . . ?
O2 C42 C43 C44 -179.89(13) . . . . ?
C41 C42 C43 C44 0.4(2) . . . . ?
C42 C43 C44 C45 1.8(2) . . . . ?
C42 C43 C44 C441 -176.80(13) . . . . ?
C43 C44 C45 C46 -2.2(2) . . . . ?
C441 C44 C45 C46 176.35(13) . . . . ?
C44 C45 C46 C41 0.5(2) . . . . ?
C42 C41 C46 C45 1.6(2) . . . . ?
C4 C41 C46 C45 -177.68(13) . . . . ?
C41 C4 N2 N2 0.00(9) . . . 1 ?
C41 C4 N2 C5 179.17(12) . . . . ?
C6 C5 N2 N2 0.00(6) . . . 1 ?
C6 C5 N2 C4 134.80(14) . . . . ?

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 N1 1 0.91(2) 1.77(2) 2.5994(16) 149.4(18)
O2 H2 N2 1 0.99(2) 1.69(2) 2.6102(16) 152.1(18)
N34 H34 N32 2 0.95(2) 1.95(2) 2.8947(18) 172.5(17)
N64 H64 N62 2_655 0.94(2) 1.92(2) 2.8574(18) 174.7(18)

_chemical_name_systematic        
'2-[(2-imidazol-4-yl)ethyliminomethyl]-5-methylphenol '
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_10aab26_0m
_database_code_depnum_ccdc_archive 'CCDC 1483392'
_audit_update_record             
;
2016-06-03 deposited with the CCDC.
2018-02-12 downloaded from the CCDC.
;

_audit_creation_date             2013-05-09T09:03:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_sum            'C22 H20 N2 O'
_chemical_formula_moiety         'C22 H20 N2 O'
_chemical_formula_weight         328.4
_chemical_absolute_configuration unk

#------------------ UNIT CELL INFORMATION -----------------------------------#
_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.9040(2)
_cell_length_b                   10.5709(3)
_cell_length_c                   20.3219(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1697.94(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9955
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      28.23


#------------------ CRYSTAL INFORMATION -------------------------------------#
_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9689
_exptl_absorpt_correction_T_max  0.9952
_exptl_absorpt_process_details   
;
SADABS (Bruker, 2004)
;

#------------------ DATA COLLECTION INFORMATION -----------------------------#
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Bruker X8 ApexII 4K Kappa CCD
;
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean 512
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0


_diffrn_reflns_number            30092
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_full        28
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_reflns_number_total             2344
_reflns_number_gt                2185
_reflns_threshold_expression     >2σ(I)
_exptl_special_details           
;
The intensity data was collected on a Bruker X8 Apex II 4K Kappa CCD
diffractometer using an exposure time of 30 seconds/frame. A total of 1938
frames were collected with a frame width of 0.5° covering up 
to θ = 28.0° with 99.8% completeness accomplished
;

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'Saint-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND 3.0c (Brandenburg & Putz, 2004)'
_computing_publication_material  'WingGX (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0552P)²+0.2451P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2344
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0882
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.233

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C13 C 0.75388(19) 0.31056(15) 0.82148(7) 0.0184(3) Uani 1 d . . .
H13 H 0.8141 0.3839 0.808 0.022 Uiso 1 calc R . .
C14 C 0.82054(18) 0.23400(16) 0.87054(7) 0.0181(3) Uani 1 d . . .
C15 C 0.73125(19) 0.12530(16) 0.88975(8) 0.0204(3) Uani 1 d . . .
H15 H 0.7761 0.0716 0.9229 0.025 Uiso 1 calc R . .
C16 C 0.57805(19) 0.09615(16) 0.86042(7) 0.0192(3) Uani 1 d . . .
H16 H 0.5191 0.0221 0.8737 0.023 Uiso 1 calc R . .
C31 C -0.36082(19) 0.26341(15) 0.58473(7) 0.0178(3) Uani 1 d . . .
C32 C -0.21148(18) 0.33418(15) 0.59545(7) 0.0164(3) Uani 1 d . . .
C33 C -0.18362(19) 0.44507(16) 0.55962(7) 0.0192(3) Uani 1 d . . .
H33 H -0.0851 0.4945 0.567 0.023 Uiso 1 calc R . .
C34 C -0.3027(2) 0.48189(16) 0.51288(8) 0.0226(3) Uani 1 d . . .
H34 H -0.2849 0.5569 0.4881 0.027 Uiso 1 calc R . .
C35 C -0.4484(2) 0.40954(16) 0.50201(8) 0.0227(3) Uani 1 d . . .
H35 H -0.5271 0.436 0.4695 0.027 Uiso 1 calc R . .
C36 C -0.4806(2) 0.29968(16) 0.53776(7) 0.0204(3) Uani 1 d . . .
H36 H -0.5802 0.2513 0.5305 0.024 Uiso 1 calc R . .
C41 C -0.48090(18) 0.05410(15) 0.62318(7) 0.0184(3) Uani 1 d . . .
H41A H -0.5912 0.086 0.6071 0.022 Uiso 1 calc R . .
H41B H -0.4978 0.0203 0.6681 0.022 Uiso 1 calc R . .
C42 C -0.42025(19) -0.05202(16) 0.57817(8) 0.0214(3) Uani 1 d . . .
H42A H -0.315 -0.0877 0.5956 0.032 Uiso 1 calc R . .
H42B H -0.4 -0.0183 0.5339 0.032 Uiso 1 calc R . .
H42C H -0.5067 -0.1183 0.576 0.032 Uiso 1 calc R . .
C141 C 0.98841(19) 0.26720(16) 0.90138(8) 0.0229(3) Uani 1 d . . .
H14A H 1.0112 0.3575 0.895 0.034 Uiso 1 calc R . .
H14B H 1.0783 0.2174 0.8806 0.034 Uiso 1 calc R . .
H14C H 0.9848 0.2483 0.9486 0.034 Uiso 1 calc R . .
H1B H 0.431(4) 0.328(3) 0.7311(13) 0.072(9) Uiso 1 d . . .
C1 C 0.34223(18) 0.14457(14) 0.78492(7) 0.0163(3) Uani 1 d . . .
H1A H 0.2854 0.07 0.7988 0.02 Uiso 1 calc R . .
C11 C 0.50839(18) 0.17350(14) 0.81158(7) 0.0167(3) Uani 1 d . . .
C12 C 0.59951(19) 0.28132(14) 0.79152(7) 0.0163(3) Uani 1 d . . .
C21 C 0.10606(18) 0.19464(15) 0.71710(7) 0.0163(3) Uani 1 d . . .
C22 C 0.00558(19) 0.08906(15) 0.73444(7) 0.0176(3) Uani 1 d . . .
H22 H 0.0471 0.0305 0.766 0.021 Uiso 1 calc R . .
C23 C -0.15159(19) 0.06915(14) 0.70656(7) 0.0174(3) Uani 1 d . . .
H23 H -0.2178 -0.0024 0.7182 0.021 Uiso 1 calc R . .
C24 C -0.21028(18) 0.15745(14) 0.66076(7) 0.0163(3) Uani 1 d . . .
C25 C -0.11406(18) 0.26531(15) 0.64390(7) 0.0162(3) Uani 1 d . . .
C26 C 0.04587(18) 0.28279(15) 0.67196(7) 0.0165(3) Uani 1 d . . .
H26 H 0.1127 0.3541 0.6603 0.02 Uiso 1 calc R . .
N1 N 0.27045(16) 0.21822(12) 0.74271(6) 0.0170(3) Uani 1 d . . .
N2 N -0.36029(16) 0.15829(13) 0.62560(6) 0.0180(3) Uani 1 d . . .
O1 O 0.53941(14) 0.36067(11) 0.74462(6) 0.0211(3) Uani 1 d . . .



#------------------ MOLECULAR GEOMETRY --------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag

C13 C14 1.388(2) . ?
C13 C12 1.398(2) . ?
C13 H13 0.95 . ?
C14 C15 1.404(2) . ?
C14 C141 1.509(2) . ?
C15 C16 1.384(2) . ?
C15 H15 0.95 . ?
C16 C11 1.399(2) . ?
C16 H16 0.95 . ?
C31 N2 1.387(2) . ?
C31 C36 1.398(2) . ?
C31 C32 1.414(2) . ?
C32 C33 1.397(2) . ?
C32 C25 1.446(2) . ?
C33 C34 1.393(2) . ?
C33 H33 0.95 . ?
C34 C35 1.400(2) . ?
C34 H34 0.95 . ?
C35 C36 1.393(2) . ?
C35 H35 0.95 . ?
C36 H36 0.95 . ?
C41 N2 1.4575(19) . ?
C41 C42 1.525(2) . ?
C41 H41A 0.99 . ?
C41 H41B 0.99 . ?
C42 H42A 0.98 . ?
C42 H42B 0.98 . ?
C42 H42C 0.98 . ?
C141 H14A 0.98 . ?
C141 H14B 0.98 . ?
C141 H14C 0.98 . ?
C1 N1 1.2899(19) . ?
C1 C11 1.453(2) . ?
C1 H1A 0.95 . ?
C11 C12 1.409(2) . ?
C12 O1 1.3556(19) . ?
C21 C26 1.391(2) . ?
C21 C22 1.414(2) . ?
C21 N1 1.4217(18) 1 ?
C21 N1 1.4217(18) . ?
C22 C23 1.381(2) . ?
C22 H22 0.95 . ?
C23 C24 1.397(2) . ?
C23 H23 0.95 . ?
C24 N2 1.3843(18) . ?
C24 C25 1.413(2) . ?
C25 C26 1.399(2) . ?
C26 H26 0.95 . ?
O1 H1B 0.97(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag


C14 C13 C12 121.01(14) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 119.09(14) . . ?
C13 C14 C141 119.77(15) . . ?
C15 C14 C141 121.13(15) . . ?
C16 C15 C14 120.15(15) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C11 121.31(15) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
N2 C31 C36 129.08(14) . . ?
N2 C31 C32 109.20(13) . . ?
C36 C31 C32 121.70(14) . . ?
C33 C32 C31 119.66(13) . . ?
C33 C32 C25 133.87(14) . . ?
C31 C32 C25 106.44(13) . . ?
C34 C33 C32 118.90(15) . . ?
C34 C33 H33 120.5 . . ?
C32 C33 H33 120.5 . . ?
C33 C34 C35 120.72(15) . . ?
C33 C34 H34 119.6 . . ?
C35 C34 H34 119.6 . . ?
C36 C35 C34 121.58(15) . . ?
C36 C35 H35 119.2 . . ?
C34 C35 H35 119.2 . . ?
C35 C36 C31 117.41(15) . . ?
C35 C36 H36 121.3 . . ?
C31 C36 H36 121.3 . . ?
N2 C41 C42 111.75(12) . . ?
N2 C41 H41A 109.3 . . ?
C42 C41 H41A 109.3 . . ?
N2 C41 H41B 109.3 . . ?
C42 C41 H41B 109.3 . . ?
H41A C41 H41B 107.9 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C14 C141 H14A 109.5 . . ?
C14 C141 H14B 109.5 . . ?
H14A C141 H14B 109.5 . . ?
C14 C141 H14C 109.5 . . ?
H14A C141 H14C 109.5 . . ?
H14B C141 H14C 109.5 . . ?
N1 C1 C11 121.22(14) . . ?
N1 C1 H1A 119.4 . . ?
C11 C1 H1A 119.4 . . ?
C16 C11 C12 118.49(14) . . ?
C16 C11 C1 119.81(14) . . ?
C12 C11 C1 121.64(14) . . ?
O1 C12 C13 118.37(14) . . ?
O1 C12 C11 121.67(14) . . ?
C13 C12 C11 119.94(14) . . ?
C26 C21 C22 120.04(14) . . ?
C26 C21 N1 115.88(14) . 1 ?
C22 C21 N1 124.08(14) . 1 ?
C26 C21 N1 115.88(14) . . ?
C22 C21 N1 124.08(14) . . ?
C23 C22 C21 121.53(14) . . ?
C23 C22 H22 119.2 . . ?
C21 C22 H22 119.2 . . ?
C22 C23 C24 118.03(14) . . ?
C22 C23 H23 121 . . ?
C24 C23 H23 121 . . ?
N2 C24 C23 129.23(14) . . ?
N2 C24 C25 109.31(13) . . ?
C23 C24 C25 121.46(13) . . ?
C26 C25 C24 119.61(14) . . ?
C26 C25 C32 133.79(15) . . ?
C24 C25 C32 106.54(13) . . ?
C21 C26 C25 119.29(14) . . ?
C21 C26 H26 120.4 . . ?
C25 C26 H26 120.4 . . ?
C1 N1 C21 122.66(14) . . ?
C24 N2 C31 108.47(13) . . ?
C24 N2 C41 124.95(13) . . ?
C31 N2 C41 125.66(12) . . ?
C12 O1 H1B 106.8(17) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 C13 C14 C15 0.4(2) . . . . ?
C12 C13 C14 C141 179.28(14) . . . . ?
C13 C14 C15 C16 -0.7(2) . . . . ?
C141 C14 C15 C16 -179.50(14) . . . . ?
C14 C15 C16 C11 -0.2(2) . . . . ?
N2 C31 C32 C33 -179.98(13) . . . . ?
C36 C31 C32 C33 1.6(2) . . . . ?
N2 C31 C32 C25 1.85(16) . . . . ?
C36 C31 C32 C25 -176.54(13) . . . . ?
C31 C32 C33 C34 -1.4(2) . . . . ?
C25 C32 C33 C34 176.15(16) . . . . ?
C32 C33 C34 C35 0.2(2) . . . . ?
C33 C34 C35 C36 0.8(2) . . . . ?
C34 C35 C36 C31 -0.6(2) . . . . ?
N2 C31 C36 C35 -178.65(14) . . . . ?
C32 C31 C36 C35 -0.6(2) . . . . ?
C15 C16 C11 C12 1.3(2) . . . . ?
C15 C16 C11 C1 -175.98(14) . . . . ?
N1 C1 C11 C16 175.86(14) . . . . ?
N1 C1 C11 C12 -1.4(2) . . . . ?
C14 C13 C12 O1 178.98(13) . . . . ?
C14 C13 C12 C11 0.7(2) . . . . ?
C16 C11 C12 O1 -179.79(13) . . . . ?
C1 C11 C12 O1 -2.5(2) . . . . ?
C16 C11 C12 C13 -1.6(2) . . . . ?
C1 C11 C12 C13 175.72(13) . . . . ?
C26 C21 C22 C23 1.3(2) . . . . ?
N1 C21 C22 C23 -178.19(13) 1 . . . ?
N1 C21 C22 C23 -178.19(13) . . . . ?
C21 C22 C23 C24 -0.6(2) . . . . ?
C22 C23 C24 N2 179.02(14) . . . . ?
C22 C23 C24 C25 -1.0(2) . . . . ?
N2 C24 C25 C26 -178.07(13) . . . . ?
C23 C24 C25 C26 2.0(2) . . . . ?
N2 C24 C25 C32 -0.49(16) . . . . ?
C23 C24 C25 C32 179.57(13) . . . . ?
C33 C32 C25 C26 -1.5(3) . . . . ?
C31 C32 C25 C26 176.26(16) . . . . ?
C33 C32 C25 C24 -178.62(15) . . . . ?
C31 C32 C25 C24 -0.83(16) . . . . ?
C22 C21 C26 C25 -0.3(2) . . . . ?
N1 C21 C26 C25 179.20(12) 1 . . . ?
N1 C21 C26 C25 179.20(12) . . . . ?
C24 C25 C26 C21 -1.3(2) . . . . ?
C32 C25 C26 C21 -178.06(15) . . . . ?
C11 C1 N1 N1 0.0(3) . . . 1 ?
C11 C1 N1 C21 -178.14(13) . . . . ?
C26 C21 N1 N1 0.0(6) . . . 1 ?
C22 C21 N1 N1 0.0(5) . . . 1 ?
C26 C21 N1 C1 179.99(14) . . . . ?
C22 C21 N1 C1 -0.5(2) . . . . ?
N1 C21 N1 C1 0(4) 1 . . . ?
C23 C24 N2 C31 -178.41(15) . . . . ?
C25 C24 N2 C31 1.65(16) . . . . ?
C23 C24 N2 C41 -8.9(2) . . . . ?
C25 C24 N2 C41 171.16(13) . . . . ?
C36 C31 N2 C24 176.04(15) . . . . ?
C32 C31 N2 C24 -2.19(16) . . . . ?
C36 C31 N2 C41 6.6(2) . . . . ?
C32 C31 N2 C41 -171.60(13) . . . . ?
C42 C41 N2 C24 -76.58(18) . . . . ?
C42 C41 N2 C31 91.14(17) . . . . ?

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 H1B N1 1 0.97(3) 1.73(3) 2.6055(17) 148(2)
C41 H41B O1 3_546 0.99 2.47 3.4077(19) 158

_chemical_name_systematic        
'2-(9-ethylcarbazol-3-yliminomethyl)-5-methylphenol '
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_10aab24_0m
_database_code_depnum_ccdc_archive 'CCDC 1483391'
_audit_update_record             
;
2016-06-03 deposited with the CCDC.
2018-02-12 downloaded from the CCDC.
;

_audit_creation_date             2013-05-08T13:58:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_sum            'C18 H18 N2 O'
_chemical_formula_moiety         'C18 H18 N2 O'
_chemical_formula_weight         278.34

#------------------ UNIT CELL INFORMATION -----------------------------------#
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0722(3)
_cell_length_b                   8.3073(3)
_cell_length_c                   14.1215(6)
_cell_angle_alpha                98.482(2)
_cell_angle_beta                 96.914(2)
_cell_angle_gamma                94.487(2)
_cell_volume                     696.07(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4662
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      31.61

#------------------ CRYSTAL INFORMATION -------------------------------------#
_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9682
_exptl_absorpt_correction_T_max  0.9942
_exptl_absorpt_process_details   
;
SADABS (Bruker, 2004)
;

#------------------ DATA COLLECTION INFORMATION -----------------------------#
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Bruker X8 ApexII 4K Kappa CCD
;
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean 512
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0

_diffrn_reflns_number            12530
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_full        28
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_reflns_number_total             3315
_reflns_number_gt                2805
_reflns_threshold_expression     >2σ(I)
_exptl_special_details           
;
The intensity data was collected on a Bruker X8 Apex II 4K Kappa CCD
diffractometer using an exposure time of 30 seconds/frame. A total of 1882
frames were collected with a frame width of 0.5° covering up 
to θ = 28.0° with 99.4% completeness accomplished
;


#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'Saint-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND 3.0c (Brandenburg & Putz, 2004)'
_computing_publication_material  'WingGX (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0600P)²+0.2885P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3315
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1221
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.397

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C1 C 0.2586(2) 0.21949(15) 0.32757(9) 0.0145(3) Uani 1 d . . .
H1A H 0.1119 0.2421 0.3055 0.017 Uiso 1 calc R . .
C2 C 0.2062(2) 0.35644(15) 0.48069(9) 0.0162(3) Uani 1 d . . .
H2A H 0.0662 0.3816 0.4446 0.019 Uiso 1 calc R . .
H2B H 0.2847 0.4597 0.5177 0.019 Uiso 1 calc R . .
C3 C 0.1553(2) 0.23549(15) 0.54922(9) 0.0152(3) Uani 1 d . . .
H3A H 0.0852 0.1316 0.5098 0.018 Uiso 1 calc R . .
H3B H 0.2984 0.2123 0.5836 0.018 Uiso 1 calc R . .
C11 C 0.3804(2) 0.11789(14) 0.26249(9) 0.0133(3) Uani 1 d . . .
C12 C 0.5939(2) 0.07540(15) 0.29480(9) 0.0136(3) Uani 1 d . . .
C13 C 0.6997(2) -0.03289(15) 0.23376(9) 0.0148(3) Uani 1 d . . .
H13 H 0.8423 -0.0627 0.2563 0.018 Uiso 1 calc R . .
C14 C 0.5992(2) -0.09750(15) 0.14062(9) 0.0153(3) Uani 1 d . . .
C15 C 0.3887(2) -0.05301(16) 0.10831(9) 0.0164(3) Uani 1 d . . .
H15 H 0.3191 -0.0951 0.0446 0.02 Uiso 1 calc R . .
C16 C 0.2816(2) 0.05204(15) 0.16886(9) 0.0156(3) Uani 1 d . . .
H16 H 0.1379 0.0799 0.1463 0.019 Uiso 1 calc R . .
C31 C 0.0068(2) 0.28911(15) 0.62300(9) 0.0136(3) Uani 1 d . . .
C32 C -0.2017(2) 0.21763(15) 0.62671(9) 0.0155(3) Uani 1 d . . .
H32 H -0.2783 0.131 0.5801 0.019 Uiso 1 calc R . .
C33 C -0.1276(2) 0.40621(15) 0.75984(9) 0.0145(3) Uani 1 d . . .
C34 C 0.0588(2) 0.41189(14) 0.70804(9) 0.0133(3) Uani 1 d . . .
C35 C 0.2454(2) 0.52333(15) 0.74699(9) 0.0157(3) Uani 1 d . . .
H35 H 0.3715 0.5311 0.7135 0.019 Uiso 1 calc R . .
C36 C 0.2426(2) 0.62153(15) 0.83491(9) 0.0173(3) Uani 1 d . . .
H36 H 0.3679 0.6972 0.8616 0.021 Uiso 1 calc R . .
C37 C 0.0569(2) 0.61099(16) 0.88538(9) 0.0180(3) Uani 1 d . . .
H37 H 0.0606 0.6784 0.9462 0.022 Uiso 1 calc R . .
C38 C -0.1308(2) 0.50475(16) 0.84840(9) 0.0170(3) Uani 1 d . . .
H38 H -0.2568 0.4992 0.8821 0.02 Uiso 1 calc R . .
C141 C 0.7146(2) -0.21535(17) 0.07642(10) 0.0204(3) Uani 1 d . . .
H14A H 0.8624 -0.2276 0.1094 0.031 Uiso 1 calc R . .
H14B H 0.7304 -0.1733 0.0161 0.031 Uiso 1 calc R . .
H14C H 0.6259 -0.3219 0.062 0.031 Uiso 1 calc R . .
N1 N 0.34694(18) 0.27856(13) 0.41401(8) 0.0155(2) Uani 1 d . . .
N2 N -0.28535(19) 0.28870(14) 0.70755(8) 0.0168(2) Uani 1 d . . .
O1 O 0.69828(16) 0.13446(11) 0.38433(7) 0.0182(2) Uani 1 d . . .
H2C H -0.411(3) 0.251(2) 0.7285(13) 0.030(5) Uiso 1 d . . .
H1B H 0.590(4) 0.198(3) 0.4146(15) 0.049(6) Uiso 1 d . . .



#------------------ MOLECULAR GEOMETRY --------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag

C1 N1 1.2817(16) . ?
C1 C11 1.4616(16) . ?
C1 H1A 0.95 . ?
C2 N1 1.4617(15) . ?
C2 C3 1.5335(17) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C31 1.4997(17) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C11 C16 1.3971(17) . ?
C11 C12 1.4107(18) . ?
C12 O1 1.3478(15) . ?
C12 C13 1.4000(17) . ?
C13 C14 1.3921(18) . ?
C13 H13 0.95 . ?
C14 C15 1.4009(18) . ?
C14 C141 1.5063(17) . ?
C15 C16 1.3851(17) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C31 C32 1.3659(18) . ?
C31 C34 1.4419(17) . ?
C32 N2 1.3776(16) . ?
C32 H32 0.95 . ?
C33 N2 1.3735(17) . ?
C33 C38 1.3931(18) . ?
C33 C34 1.4211(17) . ?
C34 C35 1.4071(18) . ?
C35 C36 1.3841(18) . ?
C35 H35 0.95 . ?
C36 C37 1.4084(19) . ?
C36 H36 0.95 . ?
C37 C38 1.3833(19) . ?
C37 H37 0.95 . ?
C38 H38 0.95 . ?
C141 H14A 0.98 . ?
C141 H14B 0.98 . ?
C141 H14C 0.98 . ?
N2 H2C 0.904(19) . ?
O1 H1B 0.97(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag

N1 C1 C11 120.95(11) . . ?
N1 C1 H1A 119.5 . . ?
C11 C1 H1A 119.5 . . ?
N1 C2 C3 107.00(10) . . ?
N1 C2 H2A 110.3 . . ?
C3 C2 H2A 110.3 . . ?
N1 C2 H2B 110.3 . . ?
C3 C2 H2B 110.3 . . ?
H2A C2 H2B 108.6 . . ?
C31 C3 C2 116.15(10) . . ?
C31 C3 H3A 108.2 . . ?
C2 C3 H3A 108.2 . . ?
C31 C3 H3B 108.2 . . ?
C2 C3 H3B 108.2 . . ?
H3A C3 H3B 107.4 . . ?
C16 C11 C12 118.56(11) . . ?
C16 C11 C1 120.54(11) . . ?
C12 C11 C1 120.78(11) . . ?
O1 C12 C13 118.70(11) . . ?
O1 C12 C11 121.51(11) . . ?
C13 C12 C11 119.79(11) . . ?
C14 C13 C12 121.02(12) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C15 119.00(11) . . ?
C13 C14 C141 120.24(12) . . ?
C15 C14 C141 120.75(12) . . ?
C16 C15 C14 120.27(12) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C11 121.36(12) . . ?
C15 C16 H16 119.3 . . ?
C11 C16 H16 119.3 . . ?
C32 C31 C34 106.16(11) . . ?
C32 C31 C3 125.38(12) . . ?
C34 C31 C3 128.20(11) . . ?
C31 C32 N2 110.53(11) . . ?
C31 C32 H32 124.7 . . ?
N2 C32 H32 124.7 . . ?
N2 C33 C38 130.11(12) . . ?
N2 C33 C34 107.40(11) . . ?
C38 C33 C34 122.46(12) . . ?
C35 C34 C33 118.66(11) . . ?
C35 C34 C31 134.33(12) . . ?
C33 C34 C31 106.99(11) . . ?
C36 C35 C34 118.98(12) . . ?
C36 C35 H35 120.5 . . ?
C34 C35 H35 120.5 . . ?
C35 C36 C37 121.03(12) . . ?
C35 C36 H36 119.5 . . ?
C37 C36 H36 119.5 . . ?
C38 C37 C36 121.48(12) . . ?
C38 C37 H37 119.3 . . ?
C36 C37 H37 119.3 . . ?
C37 C38 C33 117.37(12) . . ?
C37 C38 H38 121.3 . . ?
C33 C38 H38 121.3 . . ?
C14 C141 H14A 109.5 . . ?
C14 C141 H14B 109.5 . . ?
H14A C141 H14B 109.5 . . ?
C14 C141 H14C 109.5 . . ?
H14A C141 H14C 109.5 . . ?
H14B C141 H14C 109.5 . . ?
C1 N1 C2 118.51(11) . . ?
C33 N2 C32 108.88(11) . . ?
C33 N2 H2C 125.1(11) . . ?
C32 N2 H2C 125.0(11) . . ?
C12 O1 H1B 104.1(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C31 -178.54(10) . . . . ?
N1 C1 C11 C16 179.05(11) . . . . ?
N1 C1 C11 C12 3.27(18) . . . . ?
C16 C11 C12 O1 -179.89(11) . . . . ?
C1 C11 C12 O1 -4.02(18) . . . . ?
C16 C11 C12 C13 -1.11(18) . . . . ?
C1 C11 C12 C13 174.76(11) . . . . ?
O1 C12 C13 C14 179.98(11) . . . . ?
C11 C12 C13 C14 1.17(18) . . . . ?
C12 C13 C14 C15 -0.19(18) . . . . ?
C12 C13 C14 C141 -179.30(11) . . . . ?
C13 C14 C15 C16 -0.83(19) . . . . ?
C141 C14 C15 C16 178.27(12) . . . . ?
C14 C15 C16 C11 0.88(19) . . . . ?
C12 C11 C16 C15 0.10(19) . . . . ?
C1 C11 C16 C15 -175.78(11) . . . . ?
C2 C3 C31 C32 114.34(14) . . . . ?
C2 C3 C31 C34 -72.35(16) . . . . ?
C34 C31 C32 N2 0.84(14) . . . . ?
C3 C31 C32 N2 175.37(11) . . . . ?
N2 C33 C34 C35 -179.77(11) . . . . ?
C38 C33 C34 C35 -1.13(18) . . . . ?
N2 C33 C34 C31 -1.27(14) . . . . ?
C38 C33 C34 C31 177.37(11) . . . . ?
C32 C31 C34 C35 178.43(13) . . . . ?
C3 C31 C34 C35 4.1(2) . . . . ?
C32 C31 C34 C33 0.27(14) . . . . ?
C3 C31 C34 C33 -174.06(11) . . . . ?
C33 C34 C35 C36 1.01(18) . . . . ?
C31 C34 C35 C36 -176.99(13) . . . . ?
C34 C35 C36 C37 0.11(19) . . . . ?
C35 C36 C37 C38 -1.2(2) . . . . ?
C36 C37 C38 C33 1.08(19) . . . . ?
N2 C33 C38 C37 178.39(13) . . . . ?
C34 C33 C38 C37 0.09(19) . . . . ?
C11 C1 N1 N1 0.0(2) . . . 1 ?
C11 C1 N1 C2 -170.18(11) . . . . ?
C3 C2 N1 N1 0.0(2) . . . 1 ?
C3 C2 N1 C1 103.88(13) . . . . ?
C38 C33 N2 C32 -176.70(13) . . . . ?
C34 C33 N2 C32 1.80(14) . . . . ?
C31 C32 N2 C33 -1.69(15) . . . . ?

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 H1B N1 1 0.97(2) 1.67(2) 2.5742(14) 153.2(19)

_chemical_name_systematic        
'2-[(2-indol-3-yl-ethyl)iminomethyl]-5-methylphenol '
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_10aab28_0ma
_database_code_depnum_ccdc_archive 'CCDC 1483390'
_audit_update_record             
;
2016-06-03 deposited with the CCDC.
2018-02-12 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT415_10aab28_0ma         
;
PROBLEM: Short Inter D-H..H-X       H16    ..  H23     ..       1.89 Ang.
RESPONSE: The short intermolecular bond distance of H16...H23  (dist = 1.8916(2)\%A) is due to intermolecular H bond interaction between  H16 and N23 (sym. op. 1.5-x, -1+y, 0.5+z).
;
# Added during the CSD deposition process: Friday 03 June 2016 01:19 PM
# end Validation Reply Form


_audit_creation_date             2013-05-08T14:36:36-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_sum            'C10 H10 N4 O'
_chemical_formula_moiety         'C10 H10 N4 O'
_chemical_formula_weight         202.22
_chemical_absolute_configuration unk

#------------------ UNIT CELL INFORMATION -----------------------------------#
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21 '
_symmetry_space_group_name_Hall  'P 2c -2ac '
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'

_cell_length_a                   21.079(3)
_cell_length_b                   4.4677(5)
_cell_length_c                   10.0801(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     949.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2642
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      26.96

#------------------ CRYSTAL INFORMATION -------------------------------------#
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9628
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_process_details   
;
SADABS (Bruker, 2004)
;

#------------------ DATA COLLECTION INFORMATION -----------------------------#
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Bruker X8 ApexII 4K Kappa CCD
;
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean 512
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0

_diffrn_reflns_number            11211
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.87
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_full        28
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_reflns_number_total             1201
_reflns_number_gt                1059
_reflns_threshold_expression     >2σ(I)
_exptl_special_details           
;
The intensity data was collected on a Bruker X8 Apex II 4K Kappa CCD
diffractometer using an exposure time of 160 seconds/frame. A total of 1327
frames were collected with a frame width of 0.5° covering up 
to θ = 28.0° with 100.0% completeness accomplished
;


#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'Saint-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND 3.0c (Brandenburg & Putz, 2004)'
_computing_publication_material  'WingGX (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0560P)²+0.2647P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1201
_refine_ls_number_parameters     141
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.108
_refine_ls_goodness_of_fit_ref   1.12
_refine_ls_restrained_S_all      1.119
_refine_ls_shift/su_max          0

_refine_diff_density_max         0.393
_refine_diff_density_min         -0.404

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
N1 N 0.68867(11) 0.4271(5) 0.7644(2) 0.0155(5) Uani 1 d . . .
N22 N 0.76308(11) 0.7655(5) 0.6763(2) 0.0158(5) Uani 1 d . . .
N23 N 0.80942(11) 0.9588(5) 0.7158(2) 0.0192(5) Uani 1 d . . .
H23 H 0.8337 1.075 0.6669 0.023 Uiso 1 calc R . .
N25 N 0.76446(12) 0.7298(5) 0.8939(2) 0.0168(5) Uani 1 d . . .
O1 O 0.61344(11) 0.1179(5) 0.61194(19) 0.0217(5) Uani 1 d . . .
C1 C 0.66224(14) 0.3028(6) 0.8663(2) 0.0166(6) Uani 1 d . . .
H1A H 0.6768 0.3518 0.9528 0.02 Uiso 1 calc R . .
C11 C 0.61112(13) 0.0914(6) 0.8512(3) 0.0159(5) Uani 1 d . . .
C12 C 0.58785(13) 0.0081(6) 0.7245(3) 0.0161(5) Uani 1 d . . .
C13 C 0.53697(13) -0.1884(6) 0.7145(3) 0.0184(6) Uani 1 d . . .
H13 H 0.5225 -0.2472 0.6292 0.022 Uiso 1 calc R . .
C14 C 0.50675(13) -0.3011(6) 0.8269(3) 0.0182(6) Uani 1 d . . .
C15 C 0.53043(14) -0.2214(6) 0.9524(3) 0.0191(6) Uani 1 d . . .
H15 H 0.5109 -0.2993 1.03 0.023 Uiso 1 calc R . .
C16 C 0.58161(14) -0.0318(6) 0.9641(3) 0.0182(6) Uani 1 d . . .
H16 H 0.5973 0.0169 1.0497 0.022 Uiso 1 calc R . .
C21 C 0.73721(12) 0.6333(6) 0.7822(3) 0.0154(5) Uani 1 d . . .
C24 C 0.80873(13) 0.9275(6) 0.8463(3) 0.0183(6) Uani 1 d . . .
H24 H 0.8368 1.0341 0.9028 0.022 Uiso 1 calc R . .
C141 C 0.44942(14) -0.5013(7) 0.8156(3) 0.0220(6) Uani 1 d . . .
H14A H 0.4226 -0.4324 0.7423 0.033 Uiso 1 calc R . .
H14B H 0.4252 -0.4943 0.8986 0.033 Uiso 1 calc R . .
H14C H 0.4632 -0.7073 0.7986 0.033 Uiso 1 calc R . .
H1B H 0.6416(19) 0.247(10) 0.638(4) 0.050(14) Uiso 1 d . . .



#------------------ MOLECULAR GEOMETRY --------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag


N1 C1 1.294(4) . ?
N1 C21 1.389(3) . ?
N22 C21 1.337(4) . ?
N22 N23 1.363(3) . ?
N23 C24 1.323(4) . ?
N23 H23 0.88 . ?
N25 C21 1.335(4) . ?
N25 C24 1.371(4) . ?
O1 C12 1.349(3) . ?
O1 H1B 0.87(4) . ?
C1 C11 1.441(4) . ?
C1 H1A 0.95 . ?
C11 C16 1.408(4) . ?
C11 C12 1.418(4) . ?
C12 C13 1.390(4) . ?
C13 C14 1.394(4) . ?
C13 H13 0.95 . ?
C14 C15 1.405(4) . ?
C14 C141 1.508(4) . ?
C15 C16 1.377(4) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C24 H24 0.95 . ?
C141 H14A 0.98 . ?
C141 H14B 0.98 . ?
C141 H14C 0.98 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag



C1 N1 C21 120.0(2) . . ?
C21 N22 N23 109.8(2) . . ?
C24 N23 N22 102.5(2) . . ?
C24 N23 H23 128.8 . . ?
N22 N23 H23 128.8 . . ?
C21 N25 C24 101.9(2) . . ?
C12 O1 H1B 105(3) . . ?
N1 C1 C11 121.3(2) . . ?
N1 C1 H1A 119.4 . . ?
C11 C1 H1A 119.4 . . ?
C16 C11 C12 118.2(2) . . ?
C16 C11 C1 120.1(2) . . ?
C12 C11 C1 121.7(2) . . ?
O1 C12 C13 118.5(2) . . ?
O1 C12 C11 121.6(2) . . ?
C13 C12 C11 119.9(2) . . ?
C12 C13 C14 121.4(3) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C15 118.5(2) . . ?
C13 C14 C141 121.3(2) . . ?
C15 C14 C141 120.2(3) . . ?
C16 C15 C14 120.7(3) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C11 121.2(3) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
N25 C21 N22 110.8(2) 1 . ?
N25 C21 N22 110.8(2) . . ?
N25 C21 N1 129.8(3) 1 . ?
N25 C21 N1 129.8(3) . . ?
N22 C21 N1 119.4(2) . . ?
N25 C21 N1 129.8(3) 1 1 ?
N25 C21 N1 129.8(3) . 1 ?
N22 C21 N1 119.4(2) . 1 ?
N23 C24 N25 115.0(3) . . ?
N23 C24 H24 122.5 . . ?
N25 C24 H24 122.5 . . ?
C14 C141 H14A 109.5 . . ?
C14 C141 H14B 109.5 . . ?
H14A C141 H14B 109.5 . . ?
C14 C141 H14C 109.5 . . ?
H14A C141 H14C 109.5 . . ?
H14B C141 H14C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 N22 N23 C24 0.5(3) . . . . ?
C21 N1 C1 C11 179.0(2) . . . . ?
N1 C1 C11 C16 -177.6(3) . . . . ?
N1 C1 C11 C12 0.6(4) . . . . ?
C16 C11 C12 O1 179.7(3) . . . . ?
C1 C11 C12 O1 1.5(4) . . . . ?
C16 C11 C12 C13 0.5(4) . . . . ?
C1 C11 C12 C13 -177.7(2) . . . . ?
O1 C12 C13 C14 -177.5(2) . . . . ?
C11 C12 C13 C14 1.7(4) . . . . ?
C12 C13 C14 C15 -2.6(4) . . . . ?
C12 C13 C14 C141 176.7(2) . . . . ?
C13 C14 C15 C16 1.2(4) . . . . ?
C141 C14 C15 C16 -178.1(3) . . . . ?
C14 C15 C16 C11 1.0(4) . . . . ?
C12 C11 C16 C15 -1.8(4) . . . . ?
C1 C11 C16 C15 176.4(3) . . . . ?
C24 N25 C21 N25 0(13) . . . 1 ?
N25 N25 C21 N22 0.0(11) 1 . . . ?
C24 N25 C21 N22 -0.4(3) . . . . ?
N25 N25 C21 N1 0.0(10) 1 . . . ?
C24 N25 C21 N1 179.6(3) . . . . ?
N25 N25 C21 N1 0.0(10) 1 . . 1 ?
C24 N25 C21 N1 179.6(3) . . . 1 ?
N23 N22 C21 N25 0.0(3) . . . 1 ?
N23 N22 C21 N25 0.0(3) . . . . ?
N23 N22 C21 N1 179.9(2) . . . . ?
N23 N22 C21 N1 179.9(2) . . . 1 ?
C1 N1 C21 N25 1.5(4) . . . 1 ?
C1 N1 C21 N25 1.5(4) . . . . ?
C1 N1 C21 N22 -178.4(2) . . . . ?
C1 N1 C21 N1 0E1(10) . . . 1 ?
N22 N23 C24 N25 -0.8(3) . . . . ?
N25 N25 C24 N23 0.0(6) 1 . . . ?
C21 N25 C24 N23 0.8(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
O1 H1B N1 1 0.87(4) 1.80(5) 2.605(3) 152(4)
C1 H1A N25 1 0.95 2.57 2.892(4) 99.9
C16 H16 N23 4_645 0.95 2.6 3.423(4) 145.8
C24 H24 O1 4_665 0.95 2.38 3.254(4) 152.1

_chemical_name_systematic        
'5-methyl-2-(1,2,4-triazol-3-yliminomethyl)phenol '
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_10tab4_0m
_database_code_depnum_ccdc_archive 'CCDC 1483393'
_audit_update_record             
;
2016-06-03 deposited with the CCDC.
2018-02-12 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT415_10tab4_0m           
;
PROBLEM: Short Inter D-H..H-X       H3     ..  H5B     ..       2.05 Ang.
RESPONSE: The short intermolecular bond distance of H3...H5B  (dist = 2.05)\%A) is due to intermolecular H bond interaction between  O3 and O2 (sym. op. -x+1,-y+1,-z+1) and therefore by default between O3 and H5B-C5 (sym. op. x, -1+y, z).
;
# Added during the CSD deposition process: Friday 03 June 2016 01:19 PM
# end Validation Reply Form


_audit_creation_date             2010-12-20T12:44:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'




#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_sum            'C16 H17 N O2'
_chemical_formula_moiety         'C16 H17 N O2'
_chemical_formula_weight         255.31

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3079(5)
_cell_length_b                   11.7966(8)
_cell_length_c                   15.5593(11)
_cell_angle_alpha                89.413(4)
_cell_angle_beta                 77.258(3)
_cell_angle_gamma                80.098(4)
_cell_volume                     1288.28(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4752
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      27.62


#------------------ CRYSTAL INFORMATION -------------------------------------#
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.9931
_exptl_absorpt_process_details   
;
SADABS (Bruker, 2004)
;

#------------------ DATA COLLECTION INFORMATION -----------------------------#
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Bruker X8 ApexII 4K Kappa CCD
;
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean 512
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0


_diffrn_reflns_number            24644
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.34
_diffrn_reflns_theta_max         28
_diffrn_reflns_theta_full        28
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_reflns_number_total             6114
_reflns_number_gt                4448
_reflns_threshold_expression     >2σ(I)
_exptl_special_details           
;
The intensity data was collected on a Bruker X8 Apex II 4K Kappa CCD
diffractometer using an exposure time of 20 seconds/frame. A total of 1899
frames were collected with a frame width of 0.5° covering up 
to θ = 28.0° with 98.3% completeness accomplished
;

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'Saint-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND 3.0c (Brandenburg & Putz, 2004)'
_computing_publication_material  'WingGX (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0776P)²+0.5323P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6114
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1629
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.787
_refine_diff_density_min         -0.691

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C441 C 0.3911(3) 0.99381(18) 0.11969(12) 0.0240(4) Uani 1 d . . .
H44A H 0.5131 0.9415 0.1141 0.036 Uiso 1 calc R . .
H44B H 0.4102 1.0611 0.0835 0.036 Uiso 1 calc R . .
H44C H 0.3004 0.9538 0.0997 0.036 Uiso 1 calc R . .
O2 O 0.39857(18) 0.96021(11) 0.43161(8) 0.0187(3) Uani 1 d . . .
H2 H 0.344 0.9927 0.4806 0.028 Uiso 1 calc R . .
O6 O 0.1316(2) 1.26463(11) 1.04437(8) 0.0232(3) Uani 1 d . . .
H6C H 0.157 1.3314 1.0448 0.035 Uiso 1 calc R . .
C4 C 0.1195(3) 1.16237(15) 0.47600(12) 0.0173(4) Uani 1 d . . .
H4 H 0.0177 1.2261 0.4867 0.021 Uiso 1 calc R . .
C5 C 0.1631(3) 1.18888(16) 0.62557(11) 0.0189(4) Uani 1 d . . .
H5A H 0.0551 1.2535 0.6294 0.023 Uiso 1 calc R . .
H5B H 0.277 1.2214 0.6299 0.023 Uiso 1 calc R . .
C6 C 0.1175(3) 1.10938(16) 0.70136(11) 0.0189(4) Uani 1 d . . .
H6A H -0.0105 1.0908 0.7037 0.023 Uiso 1 calc R . .
H6B H 0.2102 1.0365 0.689 0.023 Uiso 1 calc R . .
C41 C 0.1758(2) 1.11084(15) 0.39035(11) 0.0159(4) Uani 1 d . . .
C42 C 0.3231(2) 1.01107(14) 0.37027(11) 0.0149(4) Uani 1 d . . .
C43 C 0.3865(2) 0.97467(15) 0.28080(12) 0.0165(4) Uani 1 d . . .
H43 H 0.4824 0.9082 0.2657 0.02 Uiso 1 calc R . .
C44 C 0.3141(3) 1.03221(15) 0.21441(11) 0.0170(4) Uani 1 d . . .
C45 C 0.1663(3) 1.12839(15) 0.23584(12) 0.0172(4) Uani 1 d . . .
H45 H 0.1137 1.1671 0.1907 0.021 Uiso 1 calc R . .
C46 C 0.0988(3) 1.16582(15) 0.32173(12) 0.0174(4) Uani 1 d . . .
H46 H -0.0017 1.23 0.3356 0.021 Uiso 1 calc R . .
C61 C 0.1208(2) 1.15630(15) 0.79085(11) 0.0158(4) Uani 1 d . . .
C62 C 0.1601(3) 1.26463(16) 0.80592(12) 0.0183(4) Uani 1 d . . .
H62 H 0.184 1.3139 0.7576 0.022 Uiso 1 calc R . .
C63 C 0.1655(3) 1.30330(15) 0.88928(12) 0.0172(4) Uani 1 d . . .
H63 H 0.1937 1.3777 0.8971 0.021 Uiso 1 calc R . .
C64 C 0.1299(3) 1.23333(16) 0.96105(11) 0.0172(4) Uani 1 d . . .
C65 C 0.0889(3) 1.12506(16) 0.94726(12) 0.0212(4) Uani 1 d . . .
H65 H 0.0628 1.0763 0.9958 0.025 Uiso 1 calc R . .
C66 C 0.0856(3) 1.08762(16) 0.86390(12) 0.0206(4) Uani 1 d . . .
H66 H 0.0585 1.0129 0.8562 0.025 Uiso 1 calc R . .
N2 N 0.1987(2) 1.12767(13) 0.54074(10) 0.0178(3) Uani 1 d . . .
C1 C 0.6453(3) 0.32494(15) -0.03781(12) 0.0172(4) Uani 1 d . . .
H1 H 0.5885 0.258 -0.0349 0.021 Uiso 1 calc R . .
C2 C 0.6528(3) 0.30801(16) 0.11874(12) 0.0201(4) Uani 1 d . . .
H2A H 0.7411 0.2336 0.1152 0.024 Uiso 1 calc R . .
H2B H 0.5205 0.2933 0.1365 0.024 Uiso 1 calc R . .
C3 C 0.6908(3) 0.38893(16) 0.18506(11) 0.0177(4) Uani 1 d . . .
H3A H 0.8231 0.4028 0.165 0.021 Uiso 1 calc R . .
H3B H 0.605 0.4636 0.1848 0.021 Uiso 1 calc R . .
C11 C 0.6867(3) 0.37918(15) -0.11962(11) 0.0162(4) Uani 1 d . . .
C12 C 0.7677(3) 0.48253(15) -0.12634(12) 0.0171(4) Uani 1 d . . .
C13 C 0.8130(3) 0.52873(16) -0.21123(12) 0.0175(4) Uani 1 d . . .
H13 H 0.866 0.5972 -0.2176 0.021 Uiso 1 calc R . .
C14 C 0.7827(2) 0.47770(16) -0.28490(12) 0.0175(4) Uani 1 d . . .
C15 C 0.7023(3) 0.37597(16) -0.27686(12) 0.0181(4) Uani 1 d . . .
H15 H 0.6803 0.3407 -0.3274 0.022 Uiso 1 calc R . .
C16 C 0.6566(2) 0.32890(15) -0.19603(12) 0.0175(4) Uani 1 d . . .
H16 H 0.6031 0.2606 -0.1912 0.021 Uiso 1 calc R . .
C31 C 0.6655(2) 0.34946(15) 0.27844(11) 0.0155(4) Uani 1 d . . .
C32 C 0.6891(2) 0.42353(15) 0.34307(12) 0.0171(4) Uani 1 d . . .
H32 H 0.7181 0.4973 0.3267 0.021 Uiso 1 calc R . .
C33 C 0.6714(3) 0.39278(15) 0.43025(12) 0.0180(4) Uani 1 d . . .
H33 H 0.6881 0.445 0.4728 0.022 Uiso 1 calc R . .
C34 C 0.6290(2) 0.28482(15) 0.45542(11) 0.0165(4) Uani 1 d . . .
C35 C 0.6010(2) 0.21062(15) 0.39298(11) 0.0168(4) Uani 1 d . . .
H35 H 0.5695 0.1375 0.4098 0.02 Uiso 1 calc R . .
C36 C 0.6188(2) 0.24305(15) 0.30553(12) 0.0169(4) Uani 1 d . . .
H36 H 0.5987 0.1914 0.2634 0.02 Uiso 1 calc R . .
C141 C 0.8331(3) 0.52919(17) -0.37427(12) 0.0219(4) Uani 1 d . . .
H14A H 0.7161 0.5643 -0.3922 0.033 Uiso 1 calc R . .
H14B H 0.9047 0.4687 -0.4174 0.033 Uiso 1 calc R . .
H14C H 0.9112 0.5881 -0.3713 0.033 Uiso 1 calc R . .
N1 N 0.6819(2) 0.36317(13) 0.03326(10) 0.0188(3) Uani 1 d . . .
O1 O 0.7983(2) 0.53017(11) -0.05734(8) 0.0220(3) Uani 1 d . . .
H1A H 0.7634 0.4918 -0.0128 0.033 Uiso 1 calc R . .
O3 O 0.61976(19) 0.25677(11) 0.54131(8) 0.0215(3) Uani 1 d . . .
H3 H 0.5483 0.2077 0.555 0.032 Uiso 1 calc R . .



#------------------ MOLECULAR GEOMETRY --------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C441 C44 1.501(2) . ?
C441 H44A 0.98 . ?
C441 H44B 0.98 . ?
C441 H44C 0.98 . ?
O2 C42 1.297(2) . ?
O2 H2 0.84 . ?
O6 C64 1.355(2) . ?
O6 H6C 0.84 . ?
C4 N2 1.298(2) . ?
C4 C41 1.415(2) . ?
C4 H4 0.95 . ?
C5 N2 1.461(2) . ?
C5 C6 1.514(2) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 C61 1.510(2) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C41 C46 1.415(2) . ?
C41 C42 1.437(2) . ?
C42 C43 1.413(2) . ?
C43 C44 1.382(2) . ?
C43 H43 0.95 . ?
C44 C45 1.412(3) . ?
C45 C46 1.368(2) . ?
C45 H45 0.95 . ?
C46 H46 0.95 . ?
C61 C62 1.390(3) . ?
C61 C66 1.392(3) . ?
C62 C63 1.390(2) . ?
C62 H62 0.95 . ?
C63 C64 1.387(2) . ?
C63 H63 0.95 . ?
C64 C65 1.390(3) . ?
C65 C66 1.381(3) . ?
C65 H65 0.95 . ?
C66 H66 0.95 . ?
N2 N2 0 1 ?
C1 N1 1.296(2) . ?
C1 C11 1.415(2) . ?
C1 H1 0.95 . ?
C2 N1 1.464(2) . ?
C2 C3 1.513(3) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C31 1.503(2) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C11 C16 1.410(2) . ?
C11 C12 1.437(2) . ?
C12 O1 1.296(2) . ?
C12 C13 1.416(2) . ?
C13 C14 1.377(2) . ?
C13 H13 0.95 . ?
C14 C15 1.417(3) . ?
C14 C141 1.507(2) . ?
C15 C16 1.366(2) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?
C31 C36 1.394(3) . ?
C31 C32 1.397(2) . ?
C32 C33 1.385(2) . ?
C32 H32 0.95 . ?
C33 C34 1.394(3) . ?
C33 H33 0.95 . ?
C34 O3 1.363(2) . ?
C34 C35 1.385(3) . ?
C35 C36 1.394(2) . ?
C35 H35 0.95 . ?
C36 H36 0.95 . ?
C141 H14A 0.98 . ?
C141 H14B 0.98 . ?
C141 H14C 0.98 . ?
N1 N1 0 1 ?
O1 H1A 0.84 . ?
O3 H3 0.84 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag


C44 C441 H44A 109.5 . . ?
C44 C441 H44B 109.5 . . ?
H44A C441 H44B 109.5 . . ?
C44 C441 H44C 109.5 . . ?
H44A C441 H44C 109.5 . . ?
H44B C441 H44C 109.5 . . ?
C42 O2 H2 109.5 . . ?
C64 O6 H6C 109.5 . . ?
N2 C4 C41 123.88(17) . . ?
N2 C4 H4 118.1 . . ?
C41 C4 H4 118.1 . . ?
N2 C5 C6 111.14(15) . . ?
N2 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
N2 C5 H5B 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108 . . ?
C61 C6 C5 115.28(15) . . ?
C61 C6 H6A 108.5 . . ?
C5 C6 H6A 108.5 . . ?
C61 C6 H6B 108.5 . . ?
C5 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
C46 C41 C4 118.90(16) . . ?
C46 C41 C42 119.63(16) . . ?
C4 C41 C42 121.16(16) . . ?
O2 C42 C43 122.01(16) . . ?
O2 C42 C41 120.94(16) . . ?
C43 C42 C41 117.00(16) . . ?
C44 C43 C42 122.38(16) . . ?
C44 C43 H43 118.8 . . ?
C42 C43 H43 118.8 . . ?
C43 C44 C45 119.66(16) . . ?
C43 C44 C441 120.78(16) . . ?
C45 C44 C441 119.56(16) . . ?
C46 C45 C44 119.92(16) . . ?
C46 C45 H45 120 . . ?
C44 C45 H45 120 . . ?
C45 C46 C41 121.34(17) . . ?
C45 C46 H46 119.3 . . ?
C41 C46 H46 119.3 . . ?
C62 C61 C66 116.63(16) . . ?
C62 C61 C6 124.27(16) . . ?
C66 C61 C6 119.09(16) . . ?
C61 C62 C63 122.28(17) . . ?
C61 C62 H62 118.9 . . ?
C63 C62 H62 118.9 . . ?
C64 C63 C62 120.02(16) . . ?
C64 C63 H63 120 . . ?
C62 C63 H63 120 . . ?
O6 C64 C63 123.72(16) . . ?
O6 C64 C65 117.82(16) . . ?
C63 C64 C65 118.45(16) . . ?
C66 C65 C64 120.78(17) . . ?
C66 C65 H65 119.6 . . ?
C64 C65 H65 119.6 . . ?
C65 C66 C61 121.83(17) . . ?
C65 C66 H66 119.1 . . ?
C61 C66 H66 119.1 . . ?
C4 N2 C5 124.94(16) . . ?
N1 C1 C11 122.49(17) . . ?
N1 C1 H1 118.8 . . ?
C11 C1 H1 118.8 . . ?
N1 C2 C3 107.48(15) . . ?
N1 C2 H2A 110.2 . . ?
C3 C2 H2A 110.2 . . ?
N1 C2 H2B 110.2 . . ?
C3 C2 H2B 110.2 . . ?
H2A C2 H2B 108.5 . . ?
C31 C3 C2 116.28(15) . . ?
C31 C3 H3A 108.2 . . ?
C2 C3 H3A 108.2 . . ?
C31 C3 H3B 108.2 . . ?
C2 C3 H3B 108.2 . . ?
H3A C3 H3B 107.4 . . ?
C16 C11 C1 119.89(16) . . ?
C16 C11 C12 119.57(16) . . ?
C1 C11 C12 120.48(16) . . ?
O1 C12 C13 122.02(16) . . ?
O1 C12 C11 120.92(16) . . ?
C13 C12 C11 117.06(16) . . ?
C14 C13 C12 122.23(17) . . ?
C14 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
C13 C14 C15 119.84(16) . . ?
C13 C14 C141 120.75(17) . . ?
C15 C14 C141 119.41(16) . . ?
C16 C15 C14 119.63(16) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C11 121.67(17) . . ?
C15 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?
C36 C31 C32 117.17(16) . . ?
C36 C31 C3 124.27(16) . . ?
C32 C31 C3 118.56(16) . . ?
C33 C32 C31 122.05(17) . . ?
C33 C32 H32 119 . . ?
C31 C32 H32 119 . . ?
C32 C33 C34 119.75(17) . . ?
C32 C33 H33 120.1 . . ?
C34 C33 H33 120.1 . . ?
O3 C34 C35 122.97(16) . . ?
O3 C34 C33 117.65(16) . . ?
C35 C34 C33 119.37(16) . . ?
C34 C35 C36 120.13(16) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C31 C36 C35 121.50(17) . . ?
C31 C36 H36 119.2 . . ?
C35 C36 H36 119.2 . . ?
C14 C141 H14A 109.5 . . ?
C14 C141 H14B 109.5 . . ?
H14A C141 H14B 109.5 . . ?
C14 C141 H14C 109.5 . . ?
H14A C141 H14C 109.5 . . ?
H14B C141 H14C 109.5 . . ?
C1 N1 C2 125.42(16) . . ?
C12 O1 H1A 109.5 . . ?
C34 O3 H3 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C5 C6 C61 167.18(15) . . . . ?
N2 C4 C41 C46 -170.82(17) . . . . ?
N2 C4 C41 C42 2.7(3) . . . . ?
C46 C41 C42 O2 178.76(16) . . . . ?
C4 C41 C42 O2 5.3(3) . . . . ?
C46 C41 C42 C43 1.4(3) . . . . ?
C4 C41 C42 C43 -172.07(16) . . . . ?
O2 C42 C43 C44 -176.35(16) . . . . ?
C41 C42 C43 C44 0.9(3) . . . . ?
C42 C43 C44 C45 -2.5(3) . . . . ?
C42 C43 C44 C441 177.36(17) . . . . ?
C43 C44 C45 C46 1.6(3) . . . . ?
C441 C44 C45 C46 -178.24(17) . . . . ?
C44 C45 C46 C41 0.8(3) . . . . ?
C4 C41 C46 C45 171.34(17) . . . . ?
C42 C41 C46 C45 -2.3(3) . . . . ?
C5 C6 C61 C62 0.6(3) . . . . ?
C5 C6 C61 C66 -178.27(16) . . . . ?
C66 C61 C62 C63 0.4(3) . . . . ?
C6 C61 C62 C63 -178.57(17) . . . . ?
C61 C62 C63 C64 -0.4(3) . . . . ?
C62 C63 C64 O6 -179.72(16) . . . . ?
C62 C63 C64 C65 -0.1(3) . . . . ?
O6 C64 C65 C66 -179.73(17) . . . . ?
C63 C64 C65 C66 0.6(3) . . . . ?
C64 C65 C66 C61 -0.7(3) . . . . ?
C62 C61 C66 C65 0.2(3) . . . . ?
C6 C61 C66 C65 179.18(17) . . . . ?
C41 C4 N2 N2 0.0(2) . . . 1 ?
C41 C4 N2 C5 170.54(16) . . . . ?
C6 C5 N2 N2 0.0(2) . . . 1 ?
C6 C5 N2 C4 129.94(19) . . . . ?
N1 C2 C3 C31 178.99(14) . . . . ?
N1 C1 C11 C16 175.36(17) . . . . ?
N1 C1 C11 C12 -1.8(3) . . . . ?
C16 C11 C12 O1 -179.49(16) . . . . ?
C1 C11 C12 O1 -2.4(3) . . . . ?
C16 C11 C12 C13 0.1(2) . . . . ?
C1 C11 C12 C13 177.24(16) . . . . ?
O1 C12 C13 C14 179.25(16) . . . . ?
C11 C12 C13 C14 -0.4(3) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C12 C13 C14 C141 -179.84(16) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C141 C14 C15 C16 179.92(16) . . . . ?
C14 C15 C16 C11 0.2(3) . . . . ?
C1 C11 C16 C15 -177.20(16) . . . . ?
C12 C11 C16 C15 -0.1(3) . . . . ?
C2 C3 C31 C36 3.0(3) . . . . ?
C2 C3 C31 C32 -176.69(16) . . . . ?
C36 C31 C32 C33 1.4(3) . . . . ?
C3 C31 C32 C33 -178.88(16) . . . . ?
C31 C32 C33 C34 0.0(3) . . . . ?
C32 C33 C34 O3 177.69(15) . . . . ?
C32 C33 C34 C35 -1.4(3) . . . . ?
O3 C34 C35 C36 -177.78(15) . . . . ?
C33 C34 C35 C36 1.2(3) . . . . ?
C32 C31 C36 C35 -1.5(3) . . . . ?
C3 C31 C36 C35 178.75(16) . . . . ?
C34 C35 C36 C31 0.2(3) . . . . ?
C11 C1 N1 N1 0.00(7) . . . 1 ?
C11 C1 N1 C2 -176.39(16) . . . . ?
C3 C2 N1 N1 0.00(6) . . . 1 ?
C3 C2 N1 C1 -173.12(16) . . . . ?

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 H1A N1 1 0.84 1.81 2.566(2) 149.1
O2 H2 N2 1 0.84 1.88 2.6270(19) 146.7
O3 H3 O2 2_666 0.84 1.97 2.6111(18) 132.4
O6 H6C O1 2_676 0.84 1.74 2.5778(18) 174.2
C15 H15 O3 1_554 0.95 2.44 3.387(2) 178
C35 H35 O2 1_545 0.95 2.6 3.514(2) 162.3
C45 H45 O6 1_554 0.95 2.53 3.408(2) 154.3

_chemical_name_systematic        
'2-[2-(4-hydroxyphenyl)ethyliminomethyl]-5-methylphenol '
