# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_an_555_256trimebenzoxazole
_database_code_depnum_ccdc_archive 'CCDC 1410546'
_audit_update_record             
;
2015-07-25 deposited with the CCDC.
2015-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            2,5,6-Trimethylbenzo[d]oxazole
_chemical_melting_point          366
_chemical_formula_moiety         'C10 H11 N O'
_chemical_formula_sum            'C10 H11 N O'
_chemical_formula_weight         161.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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'

_cell_length_a                   6.1944(2)
_cell_length_b                   11.6799(3)
_cell_length_c                   11.8941(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.528(3)
_cell_angle_gamma                90.00
_cell_volume                     857.85(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(10)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      74.160

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.404
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.123
_exptl_crystal_density_meas      1.248
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84391
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova (Cu) X-ray Source'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3058
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         5.32
_diffrn_reflns_theta_max         74.16
_reflns_number_total             1751
_reflns_number_gt                1538
_reflns_threshold_expression     >2σ(I)

_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_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)+(0.0704P)²+0.1718P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0209(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1675
_refine_ls_number_parameters     132
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1191
_refine_ls_wR_factor_gt          0.1142
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.065(3) 0.5684(12) 0.1554(14) 0.027(3) Uani 0.512(13) 1 d PDU A 1
O1 O 0.1129(17) 0.7616(7) 0.1303(7) 0.0234(17) Uani 0.512(13) 1 d PDU A 1
N1A N 0.094(2) 0.7551(9) 0.1300(8) 0.0211(19) Uani 0.488(13) 1 d PDU A 2
O1A O 0.100(2) 0.5709(8) 0.1665(11) 0.0166(14) Uani 0.488(13) 1 d PDU A 2
C3 C 0.43015(19) 0.55355(11) 0.28823(9) 0.0262(3) Uani 1 1 d . . .
H3 H 0.4201 0.4754 0.3016 0.031 Uiso 1 1 calc R . .
C6 C 0.45723(19) 0.79224(10) 0.24677(9) 0.0235(3) Uani 1 1 d . A .
H6 H 0.4652 0.8704 0.2327 0.028 Uiso 1 1 calc R . .
C5 C 0.28563(18) 0.72691(10) 0.20008(9) 0.0212(3) Uani 1 1 d . . .
C4 C 0.27314(19) 0.61052(10) 0.21951(9) 0.0230(3) Uani 1 1 d . A .
C2 C 0.60317(19) 0.61770(11) 0.33643(9) 0.0252(3) Uani 1 1 d . A .
C1 C 0.61692(18) 0.73665(11) 0.31541(9) 0.0242(3) Uani 1 1 d . . .
C10 C 0.8046(2) 0.80537(12) 0.36765(10) 0.0308(3) Uani 1 1 d . A .
H10A H 0.7865 0.8843 0.3464 0.046 Uiso 1 1 calc R . .
H10B H 0.9371 0.7768 0.3416 0.046 Uiso 1 1 calc R . .
H10C H 0.8097 0.7988 0.4483 0.046 Uiso 1 1 calc R . .
C9 C 0.7758(2) 0.55841(12) 0.41210(10) 0.0327(3) Uani 1 1 d . . .
H9A H 0.7434 0.4782 0.4157 0.049 Uiso 1 1 calc R A .
H9B H 0.7797 0.5908 0.4864 0.049 Uiso 1 1 calc R . .
H9C H 0.9141 0.5686 0.3823 0.049 Uiso 1 1 calc R . .
C7 C -0.00486(19) 0.66195(11) 0.11135(9) 0.0249(3) Uani 1 1 d D . .
C8 C -0.2096(2) 0.65700(11) 0.03916(10) 0.0293(3) Uani 1 1 d . A .
H8A H -0.1955 0.6031 -0.0207 0.044 Uiso 1 1 calc R . .
H8B H -0.2417 0.7314 0.0078 0.044 Uiso 1 1 calc R . .
H8C H -0.3247 0.6334 0.0835 0.044 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C7 1.272(12) . ?
N1 C4 1.527(17) . ?
O1 C5 1.362(8) . ?
O1 C7 1.383(10) . ?
N1A C7 1.260(12) . ?
N1A C5 1.434(9) . ?
O1A C4 1.288(16) . ?
O1A C7 1.384(9) . ?
C3 C4 1.3897(16) . ?
C3 C2 1.3934(17) . ?
C3 H3 0.9300 . ?
C6 C5 1.3882(17) . ?
C6 C1 1.3925(16) . ?
C6 H6 0.9300 . ?
C5 C4 1.3822(17) . ?
C2 C1 1.4155(19) . ?
C2 C9 1.5103(16) . ?
C1 C10 1.5058(17) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C7 C8 1.4753(17) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?

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
C7 N1 C4 100.1(10) . . ?
C5 O1 C7 103.2(5) . . ?
C7 N1A C5 105.8(5) . . ?
C4 O1A C7 107.3(7) . . ?
C4 C3 C2 117.67(11) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C5 C6 C1 117.66(11) . . ?
C5 C6 H6 121.2 . . ?
C1 C6 H6 121.2 . . ?
O1 C5 C4 110.0(4) . . ?
O1 C5 C6 128.3(4) . . ?
C4 C5 C6 121.67(11) . . ?
C4 C5 N1A 105.6(5) . . ?
C6 C5 N1A 132.7(5) . . ?
O1A C4 C5 109.1(4) . . ?
O1A C4 C3 129.3(4) . . ?
C5 C4 C3 121.56(11) . . ?
C5 C4 N1 106.8(5) . . ?
C3 C4 N1 131.6(5) . . ?
C3 C2 C1 120.67(11) . . ?
C3 C2 C9 118.95(12) . . ?
C1 C2 C9 120.37(11) . . ?
C6 C1 C2 120.76(11) . . ?
C6 C1 C10 118.87(11) . . ?
C2 C1 C10 120.37(11) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 C9 H9A 109.5 . . ?
C2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1A C7 N1 121.6(9) . . ?
N1 C7 O1 119.8(8) . . ?
N1A C7 O1A 112.2(7) . . ?
O1 C7 O1A 110.4(7) . . ?
N1A C7 C8 121.3(4) . . ?
N1 C7 C8 117.0(8) . . ?
O1 C7 C8 123.1(3) . . ?
O1A C7 C8 126.5(6) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
C7 O1 C5 C4 1.4(6) . . . . ?
C7 O1 C5 C6 -179.7(2) . . . . ?
C7 O1 C5 N1A -23(9) . . . . ?
C1 C6 C5 O1 -179.5(5) . . . . ?
C1 C6 C5 C4 -0.65(16) . . . . ?
C1 C6 C5 N1A 177.9(7) . . . . ?
C7 N1A C5 O1 154(10) . . . . ?
C7 N1A C5 C4 -2.1(8) . . . . ?
C7 N1A C5 C6 179.2(3) . . . . ?
C7 O1A C4 C5 -0.2(9) . . . . ?
C7 O1A C4 C3 178.9(3) . . . . ?
C7 O1A C4 N1 7(28) . . . . ?
O1 C5 C4 O1A -0.8(7) . . . . ?
C6 C5 C4 O1A -179.8(6) . . . . ?
N1A C5 C4 O1A 1.4(7) . . . . ?
O1 C5 C4 C3 -180.0(4) . . . . ?
C6 C5 C4 C3 1.04(16) . . . . ?
N1A C5 C4 C3 -177.8(5) . . . . ?
O1 C5 C4 N1 -1.1(8) . . . . ?
C6 C5 C4 N1 179.9(6) . . . . ?
N1A C5 C4 N1 1.1(8) . . . . ?
C2 C3 C4 O1A -179.7(7) . . . . ?
C2 C3 C4 C5 -0.65(16) . . . . ?
C2 C3 C4 N1 -179.2(8) . . . . ?
C7 N1 C4 O1A -173(29) . . . . ?
C7 N1 C4 C5 0.3(11) . . . . ?
C7 N1 C4 C3 179.0(3) . . . . ?
C4 C3 C2 C1 -0.08(16) . . . . ?
C4 C3 C2 C9 179.64(10) . . . . ?
C5 C6 C1 C2 -0.07(15) . . . . ?
C5 C6 C1 C10 -179.74(9) . . . . ?
C3 C2 C1 C6 0.43(16) . . . . ?
C9 C2 C1 C6 -179.28(10) . . . . ?
C3 C2 C1 C10 -179.90(10) . . . . ?
C9 C2 C1 C10 0.38(16) . . . . ?
C5 N1A C7 N1 2.6(13) . . . . ?
C5 N1A C7 O1 -48(14) . . . . ?
C5 N1A C7 O1A 2.0(10) . . . . ?
C5 N1A C7 C8 -178.6(3) . . . . ?
C4 N1 C7 N1A -1.9(14) . . . . ?
C4 N1 C7 O1 0.7(13) . . . . ?
C4 N1 C7 O1A 2(7) . . . . ?
C4 N1 C7 C8 179.3(4) . . . . ?
C5 O1 C7 N1A 129(14) . . . . ?
C5 O1 C7 N1 -1.3(11) . . . . ?
C5 O1 C7 O1A -1.5(8) . . . . ?
C5 O1 C7 C8 -179.9(3) . . . . ?
C4 O1A C7 N1A -1.2(11) . . . . ?
C4 O1A C7 N1 -178(8) . . . . ?
C4 O1A C7 O1 1.1(10) . . . . ?
C4 O1A C7 C8 179.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.957
_diffrn_reflns_theta_full        68.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.045

