# 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_anna_diaryl_dimethoxy_111
_database_code_depnum_ccdc_archive 'CCDC 1417939'
_audit_update_record             
;
2015-08-10 deposited with the CCDC.
2015-09-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        bis-(4-methoxyphenyl)-amine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H15 N O2'
_chemical_formula_sum            'C14 H15 N O2'
_chemical_formula_weight         229.27

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           orthorhombic
_symmetry_space_group_name_H-M   'C 2 c b'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, y, -z+1/2'
'x, -y, -z'
'x+1/2, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'x+1, -y+1/2, z+1/2'

_cell_length_a                   6.14510(10)
_cell_length_b                   26.7789(5)
_cell_length_c                   7.39200(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1216.42(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    292.89(11)
_cell_measurement_reflns_used    9086
_cell_measurement_theta_min      5.9640
_cell_measurement_theta_max      73.7020

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_crystal_preparation       'RECRYST FROM hexane'
_exptl_absorpt_coefficient_mu    0.674
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39591
_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      292.89(11)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'sealed X-ray tube'
_diffrn_radiation_monochromator  graphite
_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            12894
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.30
_diffrn_reflns_theta_max         74.14
_reflns_number_total             1156
_reflns_number_gt                1134
_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)+(0.0535P)²+0.1232P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1156
_refine_ls_number_parameters     82
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0904
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_refine_ls_shift/su_max          0.000
_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
H1 H 1.126(6) 0.0000 0.0000 0.093(11) Uiso 1 2 d S . .
N1 N 0.9908(3) 0.0000 0.0000 0.0553(4) Uani 1 2 d S . .
C5 C 0.5956(2) -0.10308(5) 0.08133(15) 0.0486(3) Uani 1 1 d . . .
H5 H 0.4627 -0.1085 0.1382 0.058 Uiso 1 1 calc R . .
C6 C 0.6877(2) -0.05576(5) 0.07974(15) 0.0477(3) Uani 1 1 d . . .
H6 H 0.6152 -0.0295 0.1361 0.057 Uiso 1 1 calc R . .
C2 C 0.9907(2) -0.08662(5) -0.08904(15) 0.0502(3) Uani 1 1 d . . .
H2 H 1.1226 -0.0813 -0.1476 0.060 Uiso 1 1 calc R . .
C3 C 0.9007(2) -0.13379(5) -0.08690(16) 0.0525(4) Uani 1 1 d . . .
H3 H 0.9735 -0.1601 -0.1427 0.063 Uiso 1 1 calc R . .
C1 C 0.8862(2) -0.04676(4) -0.00440(13) 0.0445(3) Uani 1 1 d . . .
O1 O 0.6277(2) -0.19044(3) -0.01076(14) 0.0654(3) Uani 1 1 d . . .
C4 C 0.7033(2) -0.14238(5) -0.00257(15) 0.0487(3) Uani 1 1 d . . .
C7 C 0.4349(3) -0.20218(6) 0.0842(3) 0.0815(6) Uani 1 1 d . . .
H7A H 0.4559 -0.1960 0.2109 0.122 Uiso 1 1 calc R . .
H7B H 0.3998 -0.2368 0.0661 0.122 Uiso 1 1 calc R . .
H7C H 0.3178 -0.1818 0.0402 0.122 Uiso 1 1 calc R . .

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 0.0408(10) 0.0517(8) 0.0734(10) 0.0056(6) 0.000 0.000
C5 0.0445(7) 0.0500(6) 0.0514(6) 0.0004(4) 0.0058(5) 0.0045(5)
C6 0.0492(8) 0.0454(6) 0.0486(6) -0.0025(4) 0.0064(5) 0.0065(5)
C2 0.0420(7) 0.0588(7) 0.0499(6) 0.0046(5) 0.0056(5) 0.0103(6)
C3 0.0528(8) 0.0516(7) 0.0531(6) -0.0022(4) 0.0032(5) 0.0150(6)
C1 0.0442(7) 0.0466(6) 0.0427(5) 0.0031(4) -0.0012(5) 0.0038(5)
O1 0.0677(8) 0.0436(5) 0.0848(7) -0.0059(4) 0.0043(6) 0.0019(5)
C4 0.0517(8) 0.0448(6) 0.0497(6) 0.0006(4) -0.0034(5) 0.0073(6)
C7 0.0678(12) 0.0559(8) 0.1207(14) -0.0021(8) 0.0073(10) -0.0111(8)

_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 C1 1.4079(16) 3 ?
N1 C1 1.4079(16) . ?
N1 H1 0.83(4) . ?
C5 C6 1.3879(18) . ?
C5 C4 1.3893(17) . ?
C5 H5 0.9300 . ?
C6 C1 1.390(2) . ?
C6 H6 0.9300 . ?
C2 C3 1.3791(19) . ?
C2 C1 1.3939(18) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(2) . ?
C3 H3 0.9300 . ?
O1 C4 1.3695(16) . ?
O1 C7 1.413(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 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
C1 N1 C1 125.67(18) 3 . ?
C1 N1 H1 117.17(9) 3 . ?
C1 N1 H1 117.17(9) . . ?
C6 C5 C4 119.59(12) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C1 121.31(11) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
C3 C2 C1 120.77(13) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 120.60(11) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C6 C1 C2 118.18(12) . . ?
C6 C1 N1 122.98(11) . . ?
C2 C1 N1 118.75(13) . . ?
C4 O1 C7 118.14(11) . . ?
O1 C4 C3 115.72(11) . . ?
O1 C4 C5 124.75(13) . . ?
C3 C4 C5 119.53(12) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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
C4 C5 C6 C1 0.03(17) . . . . ?
C1 C2 C3 C4 0.84(19) . . . . ?
C5 C6 C1 C2 0.48(17) . . . . ?
C5 C6 C1 N1 -176.23(10) . . . . ?
C3 C2 C1 C6 -0.91(17) . . . . ?
C3 C2 C1 N1 175.94(10) . . . . ?
C1 N1 C1 C6 -32.59(9) 3 . . . ?
C1 N1 C1 C2 150.72(11) 3 . . . ?
C7 O1 C4 C3 175.47(14) . . . . ?
C7 O1 C4 C5 -5.12(19) . . . . ?
C2 C3 C4 O1 179.13(11) . . . . ?
C2 C3 C4 C5 -0.31(18) . . . . ?
C6 C5 C4 O1 -179.51(11) . . . . ?
C6 C5 C4 C3 -0.12(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        68.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.034

_iucr_refine_instructions_details 
;
TITL anna_diaryl_dimethoxy_111 in C 2 c b
CELL  1.54184   6.1451  26.7789   7.3920   90.000   90.000   90.000
ZERR     4.00   0.0001   0.0005   0.0001    0.000    0.000    0.000
LATT  -7
SYMM  1/2 + X,   Y, 1/2 - Z
SYMM    X, - Y, - Z
SYMM  1/2 + X, - Y, 1/2 + Z
SFAC  C    H    N    O
UNIT  56   60   4    8
MERG   2
OMIT     0.00 180.00
FMAP   2
PLAN   20
SIZE     0.08   0.31   0.40
ACTA   136.00
BOND
BOND   $H
CONF
LIST   4
L.S.   4
TEMP    20.00
WGHT    0.053500    0.123200
EXTI    0.002008
FVAR       4.91167
H1    2    1.126089    0.000000    0.000000    10.50000    0.09328
MOLE    1
N1    3    0.990788    0.000000    0.000000    10.50000    0.04080    0.05169 =
         0.07338    0.00559    0.00000    0.00000
C5    1    0.595642   -0.103081    0.081333    11.00000    0.04449    0.05003 =
         0.05139    0.00035    0.00583    0.00450
AFIX  43
H5    2    0.462695   -0.108451    0.138213    11.00000   -1.20000
AFIX   0
C6    1    0.687714   -0.055756    0.079743    11.00000    0.04915    0.04538 =
         0.04856   -0.00247    0.00637    0.00646
AFIX  43
H6    2    0.615186   -0.029542    0.136094    11.00000   -1.20000
AFIX   0
C2    1    0.990686   -0.086616   -0.089040    11.00000    0.04196    0.05880 =
         0.04987    0.00462    0.00562    0.01025
AFIX  43
H2    2    1.122613   -0.081332   -0.147640    11.00000   -1.20000
AFIX   0
C3    1    0.900727   -0.133794   -0.086896    11.00000    0.05285    0.05161 =
         0.05312   -0.00219    0.00319    0.01503
AFIX  43
H3    2    0.973464   -0.160073   -0.142655    11.00000   -1.20000
AFIX   0
C1    1    0.886183   -0.046759   -0.004404    11.00000    0.04418    0.04663 =
         0.04273    0.00309   -0.00122    0.00379
O1    4    0.627703   -0.190437   -0.010762    11.00000    0.06774    0.04357 =
         0.08478   -0.00586    0.00426    0.00186
C4    1    0.703320   -0.142382   -0.002575    11.00000    0.05172    0.04477 =
         0.04970    0.00061   -0.00340    0.00732
C7    1    0.434869   -0.202175    0.084211    11.00000    0.06782    0.05590 =
         0.12067   -0.00215    0.00728   -0.01114
AFIX 137
H7A   2    0.455910   -0.195968    0.210918    11.00000   -1.50000
H7B   2    0.399839   -0.236751    0.066089    11.00000   -1.50000
H7C   2    0.317821   -0.181782    0.040163    11.00000   -1.50000
HKLF    4

REM  anna_diaryl_dimethoxy_111 in C 2 c b
REM R1 =  0.0311 for   1134 Fo > 4sig(Fo)  and  0.0315 for all   1156 data
REM     82 parameters refined using      1 restraints

END

WGHT      0.0535      0.1226
REM Highest difference peak  0.131,  deepest hole -0.112,  1-sigma level  0.034
Q1    1   0.8677 -0.1390  0.0051  11.00000  0.05    0.13
Q2    1   0.6258 -0.0797  0.0207  11.00000  0.05    0.13
Q3    1   0.6222 -0.1189  0.0014  11.00000  0.05    0.12
Q4    1   0.5611  0.0000  0.0000  10.50000  0.05    0.11
Q5    1   0.7249 -0.0506 -0.0121  11.00000  0.05    0.11
Q6    1   0.9726 -0.1080 -0.0267  11.00000  0.05    0.11
Q7    1   0.6567 -0.0707 -0.0268  11.00000  0.05    0.10
Q8    1   0.4344 -0.2920  0.0334  11.00000  0.05    0.10
Q9    1   0.9786 -0.0727 -0.0073  11.00000  0.05    0.10
Q10   1   0.1715 -0.2404  0.0288  11.00000  0.05    0.09
Q11   1   0.6703 -0.1661  0.0043  11.00000  0.05    0.09
Q12   1   0.3853 -0.2591 -0.0572  11.00000  0.05    0.08
Q13   1   0.3701 -0.2333  0.0023  11.00000  0.05    0.08
Q14   1   0.5614 -0.2668 -0.0124  11.00000  0.05    0.08
Q15   1   0.3917 -0.1296 -0.0269  11.00000  0.05    0.07
Q16   1   0.2735 -0.1601 -0.0010  11.00000  0.05    0.07
Q17   1   0.7717 -0.2182  0.0290  11.00000  0.05    0.07
Q18   1   0.0739 -0.1953  0.0116  11.00000  0.05    0.07
Q19   1   1.0752 -0.1837  0.0019  11.00000  0.05    0.07
Q20   1   1.3377  0.0329  0.0231  11.00000  0.05    0.07
;
