# 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_222_bis_benzoxazole_meme
_database_code_depnum_ccdc_archive 'CCDC 1415173'
_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        "2,6-Dimethylbenzo[1,2-d:5,4-d']bis(oxazole) "
_chemical_name_common            ?
_chemical_melting_point          401-404
_chemical_formula_moiety         'C10 H8 N2 O2'
_chemical_formula_sum            'C10 H8 N2 O2'
_chemical_formula_weight         188.18

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                   3.83460(10)
_cell_length_b                   8.0536(3)
_cell_length_c                   13.7021(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.664(3)
_cell_angle_gamma                90.00
_cell_volume                     421.75(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.01(10)
_cell_measurement_reflns_used    936
_cell_measurement_theta_min      6.3630
_cell_measurement_theta_max      73.7160

_exptl_crystal_description       prizm
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.072
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             196
_exptl_absorpt_coefficient_mu    0.881
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65049
_exptl_absorpt_correction_type   multi-scan
_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      100.01(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, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1371
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         6.38
_diffrn_reflns_theta_max         73.85
_reflns_number_total             820
_reflns_number_gt                759
_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)+(0.0547P)²+0.1194P] 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       0.013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         820
_refine_ls_number_parameters     84
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0952
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.002

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 0.048(4) 0.724(2) 0.6565(11) 0.023(2) Uani 0.50 1 d PDU A 1
O1 O -0.233(3) 0.8091(16) 0.5150(6) 0.0151(15) Uani 0.50 1 d PDU A 1
O1A O 0.042(3) 0.7036(18) 0.6521(8) 0.022(2) Uani 0.50 1 d PDU A 2
N1A N -0.225(5) 0.828(2) 0.5212(10) 0.026(3) Uani 0.50 1 d PDU A 2
C1 C -0.1875(3) 0.99819(17) 0.66131(9) 0.0243(3) Uani 1 1 d . A .
H1A H -0.3275 1.0701 0.6181 0.036 Uiso 1 1 calc R . .
H1B H 0.0314 1.0513 0.6806 0.036 Uiso 1 1 calc R . .
H1C H -0.3090 0.9753 0.7184 0.036 Uiso 1 1 calc R . .
C2 C -0.1222(3) 0.84193(16) 0.61059(10) 0.0241(4) Uani 1 1 d D . .
C3 C 0.0443(3) 0.59172(16) 0.58300(10) 0.0218(3) Uani 1 1 d D . .
C4 C -0.1272(3) 0.65599(16) 0.49728(9) 0.0204(3) Uani 1 1 d D A .
C5 C -0.1788(3) 0.56821(16) 0.41032(9) 0.0226(3) Uani 1 1 d . . .
H5 H -0.2918 0.6119 0.3534 0.027 Uiso 1 1 calc R A .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.020(3) 0.019(4) 0.030(3) -0.003(2) 0.009(2) -0.0011(18)
O1 0.016(2) 0.018(4) 0.0116(19) 0.0010(17) -0.0028(14) -0.002(2)
O1A 0.019(2) 0.019(3) 0.027(3) 0.012(3) -0.0009(19) 0.006(2)
N1A 0.031(5) 0.010(2) 0.039(5) -0.003(2) 0.013(3) 0.008(2)
C1 0.0210(6) 0.0320(8) 0.0197(6) -0.0015(5) 0.0010(5) 0.0021(5)
C2 0.0182(6) 0.0218(7) 0.0336(8) 0.0070(6) 0.0098(5) 0.0017(5)
C3 0.0157(6) 0.0221(7) 0.0283(7) 0.0057(5) 0.0060(5) 0.0006(5)
C4 0.0162(6) 0.0175(7) 0.0281(7) 0.0047(5) 0.0066(5) 0.0017(4)
C5 0.0187(6) 0.0246(7) 0.0245(6) 0.0076(5) 0.0009(5) 0.0034(5)

_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 C2 1.288(14) . ?
N1 C3 1.464(18) . ?
O1 C4 1.327(13) . ?
O1 C2 1.369(9) . ?
O1A C3 1.307(14) . ?
O1A C2 1.380(11) . ?
N1A C2 1.262(13) . ?
N1A C4 1.476(17) . ?
C1 C2 1.4689(19) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C3 C5 1.3876(18) 3_566 ?
C3 C4 1.3980(18) . ?
C4 C5 1.3858(19) . ?
C5 C3 1.3876(18) 3_566 ?
C5 H5 0.9300 . ?

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
C2 N1 C3 103.0(10) . . ?
C4 O1 C2 106.2(6) . . ?
C3 O1A C2 106.7(7) . . ?
C2 N1A C4 103.7(9) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1A C2 N1 120.8(14) . . ?
N1 C2 O1 115.5(7) . . ?
N1A C2 O1A 115.0(6) . . ?
O1 C2 O1A 109.5(9) . . ?
N1A C2 C1 119.1(8) . . ?
N1 C2 C1 120.0(8) . . ?
O1 C2 C1 124.5(5) . . ?
O1A C2 C1 125.9(6) . . ?
O1A C3 C5 128.0(4) . 3_566 ?
O1A C3 C4 108.8(4) . . ?
C5 C3 C4 123.09(13) 3_566 . ?
C5 C3 N1 130.3(5) 3_566 . ?
C4 C3 N1 106.6(5) . . ?
O1 C4 C5 127.4(4) . . ?
O1 C4 C3 108.7(4) . . ?
C5 C4 C3 123.92(12) . . ?
C5 C4 N1A 130.3(5) . . ?
C3 C4 N1A 105.7(5) . . ?
C4 C5 C3 112.99(12) . 3_566 ?
C4 C5 H5 123.5 . . ?
C3 C5 H5 123.5 3_566 . ?

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
C4 N1A C2 N1 4.2(18) . . . . ?
C4 N1A C2 O1 -19(12) . . . . ?
C4 N1A C2 O1A 1.2(15) . . . . ?
C4 N1A C2 C1 -178.0(5) . . . . ?
C3 N1 C2 N1A -4.2(18) . . . . ?
C3 N1 C2 O1 -1.6(14) . . . . ?
C3 N1 C2 O1A 21(11) . . . . ?
C3 N1 C2 C1 178.0(5) . . . . ?
C4 O1 C2 N1A 158(14) . . . . ?
C4 O1 C2 N1 0.4(13) . . . . ?
C4 O1 C2 O1A -2.2(12) . . . . ?
C4 O1 C2 C1 -179.2(4) . . . . ?
C3 O1A C2 N1A 0.2(15) . . . . ?
C3 O1A C2 N1 -156(12) . . . . ?
C3 O1A C2 O1 2.4(12) . . . . ?
C3 O1A C2 C1 179.4(4) . . . . ?
C2 O1A C3 C5 -179.5(4) . . . 3_566 ?
C2 O1A C3 C4 -1.6(10) . . . . ?
C2 O1A C3 N1 45(19) . . . . ?
C2 N1 C3 O1A -132(21) . . . . ?
C2 N1 C3 C5 -178.2(4) . . . 3_566 ?
C2 N1 C3 C4 2.2(12) . . . . ?
C2 O1 C4 C5 179.9(3) . . . . ?
C2 O1 C4 C3 1.2(9) . . . . ?
C2 O1 C4 N1A -32(19) . . . . ?
O1A C3 C4 O1 0.3(9) . . . . ?
C5 C3 C4 O1 178.3(6) 3_566 . . . ?
N1 C3 C4 O1 -2.1(10) . . . . ?
O1A C3 C4 C5 -178.5(7) . . . . ?
C5 C3 C4 C5 -0.5(2) 3_566 . . . ?
N1 C3 C4 C5 179.1(7) . . . . ?
O1A C3 C4 N1A 2.3(11) . . . . ?
C5 C3 C4 N1A -179.7(8) 3_566 . . . ?
N1 C3 C4 N1A -0.1(10) . . . . ?
C2 N1A C4 O1 145(20) . . . . ?
C2 N1A C4 C5 178.8(5) . . . . ?
C2 N1A C4 C3 -2.1(13) . . . . ?
O1 C4 C5 C3 -178.1(7) . . . 3_566 ?
C3 C4 C5 C3 0.45(19) . . . 3_566 ?
N1A C4 C5 C3 179.5(10) . . . 3_566 ?

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        68.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.042

_iucr_refine_instructions_details 
;
TITL an_222_bis_benzoxazole_meme in P 21/n
CELL  1.54184   3.8346   8.0536  13.7021   90.000   94.664   90.000
ZERR     2.00   0.0001   0.0003   0.0005    0.000    0.003    0.000
LATT   1
SYMM  1/2 - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    O
UNIT  20   16   4    4
MERG   2
OMIT     0.00 180.00
SADI C2 N1 C2 N1A
SADI C2 O1 C2 O1A
SADI C3 O1A C4 O1
SADI C3 N1 C4 N1A
ISOR     0.010 N1 O1 O1A N1A
FMAP   2
PLAN   20
ACTA   136.00
BOND
BOND   $H
CONF
LIST   4
L.S.   4
WGHT    0.054700    0.119400
EXTI    0.013000
FVAR      15.37929
MOLE    1
PART    1
N1    3    0.047938    0.723843    0.656505    10.50000    0.01995    0.01919 =
         0.02982   -0.00263    0.00855   -0.00107
O1    4   -0.232727    0.809133    0.515014    10.50000    0.01563    0.01756 =
         0.01155    0.00101   -0.00281   -0.00156
PART    2
O1A   4    0.042111    0.703571    0.652098    10.50000    0.01888    0.01876 =
         0.02703    0.01221   -0.00092    0.00588
N1A   3   -0.225430    0.827507    0.521176    10.50000    0.03073    0.01046 =
         0.03943   -0.00280    0.01299    0.00819
PART    0
C1    1   -0.187478    0.998195    0.661313    11.00000    0.02098    0.03205 =
         0.01969   -0.00147    0.00104    0.00212
AFIX 137
H1A   2   -0.327496    1.070072    0.618144    11.00000   -1.50000
H1B   2    0.031439    1.051347    0.680583    11.00000   -1.50000
H1C   2   -0.309032    0.975288    0.718362    11.00000   -1.50000
AFIX   0
C2    1   -0.122207    0.841931    0.610587    11.00000    0.01818    0.02179 =
         0.03361    0.00696    0.00983    0.00165
C3    1    0.044350    0.591719    0.583001    11.00000    0.01570    0.02211 =
         0.02832    0.00568    0.00596    0.00056
C4    1   -0.127181    0.655988    0.497284    11.00000    0.01624    0.01749 =
         0.02815    0.00468    0.00659    0.00172
C5    1   -0.178786    0.568205    0.410323    11.00000    0.01867    0.02456 =
         0.02447    0.00764    0.00095    0.00338
AFIX  43
H5    2   -0.291767    0.611933    0.353410    11.00000   -1.20000
HKLF    4
 
REM  an_222_bis_benzoxazole_meme in P 21/n
REM R1 =  0.0338 for    759 Fo > 4sig(Fo)  and  0.0371 for all    820 data
REM     84 parameters refined using     28 restraints
 
END
 
WGHT      0.0546      0.1194
REM Highest difference peak  0.257,  deepest hole -0.168,  1-sigma level  0.042
Q1    1  -0.1295  0.6086  0.5495  11.00000  0.05    0.26
Q2    1  -0.1865  0.5990  0.4633  11.00000  0.05    0.18
Q3    1   0.0128  0.4946  0.5796  11.00000  0.05    0.18
Q4    1   0.0566  0.6472  0.5296  11.00000  0.05    0.17
Q5    1   0.1376  0.5270  0.5821  11.00000  0.05    0.17
Q6    1  -0.1394  0.9295  0.6296  11.00000  0.05    0.16
Q7    1  -0.0219  0.8037  0.5333  11.00000  0.05    0.16
Q8    1  -0.1425  0.7318  0.6370  11.00000  0.05    0.15
Q9    1  -0.4795  0.8171  0.4999  11.00000  0.05    0.12
Q10   1  -0.0620  1.0333  0.7282  11.00000  0.05    0.11
Q11   1  -0.1334  1.0433  0.7409  11.00000  0.05    0.11
Q12   1  -0.1384  0.6399  0.3286  11.00000  0.05    0.11
Q13   1  -0.3870  1.0076  0.6605  11.00000  0.05    0.11
Q14   1   0.2837  0.7146  0.6754  11.00000  0.05    0.11
Q15   1  -0.1487  1.0789  0.6193  11.00000  0.05    0.10
Q16   1   0.0827  0.8201  0.6245  11.00000  0.05    0.10
Q17   1   0.0138  0.9342  0.5212  11.00000  0.05    0.10
Q18   1  -0.0352  0.8198  0.4431  11.00000  0.05    0.10
Q19   1  -0.2147  0.8827  0.4533  11.00000  0.05    0.09
Q20   1  -0.0093  0.6482  0.7407  11.00000  0.05    0.09
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
