# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_22222
_database_code_depnum_ccdc_archive 'CCDC 1470002'
_audit_update_record             
;
2016-03-22 deposited with the CCDC.
2016-11-10 downloaded from the CCDC.
;
_audit_creation_date             2016-03-20
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
(R)-1-bromo-4-(2-nitro-1-(p-tolyl)ethyl)benzene
_chemical_formula_moiety         'C15 H14 Br N O2'
_chemical_formula_sum            'C15 H14 Br N O2'
_chemical_formula_weight         320.18
_chemical_absolute_configuration ad
_chemical_melting_point          '70.4 oC'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   5.4842(15)
_cell_length_b                   15.284(4)
_cell_length_c                   16.885(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1415.4(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3681
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.74
_cell_measurement_theta_min      2.41
_exptl_absorpt_coefficient_mu    2.901
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       colourless
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10253
_diffrn_reflns_theta_full        26.48
_diffrn_reflns_theta_max         26.48
_diffrn_reflns_theta_min         1.80
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_number_gt                2300
_reflns_number_total             2905
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.040(12)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2905
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0255P)²+0.5661P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0881
_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 > 2sigma(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. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  {H15A,H15B} of C15, H14 of C14, H8 of C8, H10 of C10, H11 of C11, H5 of C5,
  H1 of C1, H6 of C6, H2 of C2, H13 of C13
 At 1.5 times of:
  {H4A,H4B,H4C} of C4
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C10(H10), C11(H11), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
Br1 Br -0.10566(9) -0.33430(3) -0.45893(2) 0.07569(17) Uani 1 1 d . . .
O1 O 0.5046(6) -0.6519(2) -0.1754(2) 0.0824(9) Uani 1 1 d . . .
O2 O 0.1796(6) -0.7020(2) -0.2276(2) 0.0876(10) Uani 1 1 d . . .
N1 N 0.2854(6) -0.6551(2) -0.18139(18) 0.0535(7) Uani 1 1 d . . .
C1 C 0.1967(7) -0.4484(2) 0.0009(2) 0.0551(9) Uani 1 1 d . . .
H1 H 0.3379 -0.4810 0.0085 0.066 Uiso 1 1 calc R . .
C2 C 0.1037(8) -0.4007(2) 0.06298(19) 0.0568(8) Uani 1 1 d . . .
H2 H 0.1838 -0.4014 0.1115 0.068 Uiso 1 1 calc R . .
C3 C -0.1081(7) -0.3515(2) 0.05455(18) 0.0525(8) Uani 1 1 d . . .
C4 C -0.2106(9) -0.2981(3) 0.1219(2) 0.0747(12) Uani 1 1 d . . .
H4A H -0.3090 -0.3349 0.1551 0.112 Uiso 1 1 calc R . .
H4B H -0.3088 -0.2515 0.1011 0.112 Uiso 1 1 calc R . .
H4C H -0.0792 -0.2740 0.1525 0.112 Uiso 1 1 calc R . .
C5 C -0.2182(7) -0.3528(3) -0.0187(2) 0.0600(10) Uani 1 1 d . . .
H5 H -0.3611 -0.3211 -0.0263 0.072 Uiso 1 1 calc R . .
C6 C -0.1230(7) -0.3997(2) -0.0813(2) 0.0526(8) Uani 1 1 d . . .
H6 H -0.2011 -0.3979 -0.1301 0.063 Uiso 1 1 calc R . .
C7 C 0.0852(6) -0.44907(19) -0.07298(18) 0.0438(7) Uani 1 1 d . . .
C8 C 0.1992(6) -0.5019(2) -0.14011(19) 0.0440(7) Uani 1 1 d . . .
H8 H 0.3764 -0.4962 -0.1349 0.053 Uiso 1 1 calc R . .
C9 C 0.1318(6) -0.46726(19) -0.22179(17) 0.0417(7) Uani 1 1 d . . .
C10 C 0.2664(6) -0.4005(2) -0.2546(2) 0.0496(8) Uani 1 1 d . . .
H10 H 0.4055 -0.3810 -0.2285 0.060 Uiso 1 1 calc R . .
C11 C 0.2014(7) -0.3618(2) -0.3248(2) 0.0582(9) Uani 1 1 d . . .
H11 H 0.2953 -0.3167 -0.3459 0.070 Uiso 1 1 calc R . .
C12 C -0.0034(6) -0.3901(2) -0.36362(19) 0.0488(8) Uani 1 1 d . . .
C13 C -0.1400(7) -0.4574(2) -0.3344(2) 0.0537(9) Uani 1 1 d . . .
H13 H -0.2768 -0.4770 -0.3616 0.064 Uiso 1 1 calc R . .
C14 C -0.0718(6) -0.4962(2) -0.2632(2) 0.0513(8) Uani 1 1 d . . .
H14 H -0.1638 -0.5422 -0.2431 0.062 Uiso 1 1 calc R . .
C15 C 0.1380(7) -0.5985(2) -0.12716(19) 0.0489(8) Uani 1 1 d . . .
H15A H 0.1717 -0.6143 -0.0726 0.059 Uiso 1 1 calc R . .
H15B H -0.0342 -0.6080 -0.1370 0.059 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
Br1 0.1079(3) 0.0675(3) 0.0516(2) 0.01407(19) -0.0001(2) 0.0192(3)
O1 0.0607(18) 0.083(2) 0.104(2) -0.021(2) 0.0063(15) 0.0184(16)
O2 0.103(2) 0.077(2) 0.0825(19) -0.0268(17) 0.0021(18) -0.0117(18)
N1 0.062(2) 0.0421(18) 0.0564(18) 0.0056(15) 0.0046(15) 0.0036(15)
C1 0.0559(19) 0.055(2) 0.054(2) 0.0061(17) -0.0070(16) 0.0133(18)
C2 0.069(2) 0.058(2) 0.0437(17) 0.0040(14) -0.0051(18) 0.005(2)
C3 0.0611(19) 0.0447(18) 0.052(2) 0.0051(14) 0.0093(17) -0.0011(18)
C4 0.099(3) 0.064(2) 0.061(2) -0.002(2) 0.020(2) 0.009(2)
C5 0.0530(19) 0.066(2) 0.061(2) -0.0030(18) -0.0031(16) 0.0150(18)
C6 0.0485(18) 0.060(2) 0.0498(17) -0.0020(15) -0.0084(17) 0.0100(18)
C7 0.0464(18) 0.0378(16) 0.0472(16) 0.0035(13) 0.0011(16) -0.0023(16)
C8 0.0410(16) 0.0419(17) 0.0491(18) 0.0039(14) -0.0014(14) -0.0007(14)
C9 0.0425(17) 0.0386(16) 0.0440(15) -0.0011(13) 0.0030(15) 0.0038(15)
C10 0.0474(19) 0.0444(18) 0.057(2) 0.0019(16) -0.0027(16) -0.0066(16)
C11 0.062(2) 0.046(2) 0.066(2) 0.0129(17) 0.0132(19) -0.0058(16)
C12 0.066(2) 0.0381(18) 0.0427(18) 0.0022(15) 0.0080(15) 0.0127(16)
C13 0.059(2) 0.0505(19) 0.0520(18) -0.0020(15) -0.0077(17) -0.0032(17)
C14 0.052(2) 0.0484(18) 0.0533(18) 0.0081(15) -0.0001(17) -0.0122(18)
C15 0.0489(19) 0.0478(18) 0.0499(17) 0.0059(14) 0.0034(15) 0.0059(16)

_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
Br1 C12 1.906(3) . ?
O1 N1 1.207(4) . ?
O2 N1 1.208(4) . ?
N1 C15 1.497(4) . ?
C1 C2 1.375(5) . ?
C1 C7 1.389(5) . ?
C2 C3 1.391(5) . ?
C3 C4 1.508(5) . ?
C3 C5 1.377(5) . ?
C5 C6 1.379(5) . ?
C6 C7 1.376(5) . ?
C7 C8 1.526(5) . ?
C8 C9 1.523(4) . ?
C8 C15 1.529(5) . ?
C9 C10 1.377(4) . ?
C9 C14 1.390(5) . ?
C10 C11 1.372(5) . ?
C11 C12 1.370(5) . ?
C12 C13 1.365(5) . ?
C13 C14 1.391(5) . ?

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
O1 N1 O2 123.8(4) . . ?
O1 N1 C15 117.6(3) . . ?
O2 N1 C15 118.6(3) . . ?
C2 C1 C7 121.7(3) . . ?
C1 C2 C3 121.2(3) . . ?
C2 C3 C4 121.7(3) . . ?
C5 C3 C2 116.8(3) . . ?
C5 C3 C4 121.5(3) . . ?
C3 C5 C6 122.0(3) . . ?
C7 C6 C5 121.4(3) . . ?
C1 C7 C8 119.4(3) . . ?
C6 C7 C1 116.9(3) . . ?
C6 C7 C8 123.7(3) . . ?
C7 C8 C15 108.4(3) . . ?
C9 C8 C7 112.9(3) . . ?
C9 C8 C15 114.3(3) . . ?
C10 C9 C8 119.5(3) . . ?
C10 C9 C14 117.6(3) . . ?
C14 C9 C8 122.7(3) . . ?
C11 C10 C9 121.9(3) . . ?
C12 C11 C10 119.3(3) . . ?
C11 C12 Br1 120.2(3) . . ?
C13 C12 Br1 118.8(3) . . ?
C13 C12 C11 121.0(3) . . ?
C12 C13 C14 119.1(3) . . ?
C9 C14 C13 121.0(3) . . ?
N1 C15 C8 110.6(3) . . ?

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'chloroform and n-hexane'
