# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
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data_mo_2016150_0m
_database_code_depnum_ccdc_archive 'CCDC 1478345'

_audit_update_record             
;
2016-05-05 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;
_audit_creation_date             2016-04-20
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C14 H10 Br N O2)'
_chemical_formula_sum            'C28 H20 Br2 N2 O4'
_chemical_formula_weight         608.28
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   4.4197(5)
_cell_length_b                   11.6677(13)
_cell_length_c                   22.915(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1181.7(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    986
_cell_measurement_temperature    173
_cell_measurement_theta_max      20.277
_cell_measurement_theta_min      3.188
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.470
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.4529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1131 before and 0.0752 after correction.
The Ratio of minimum to maximum transmission is 0.6077.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1091
_diffrn_reflns_av_unetI/netI     0.1028
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8364
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.002
_diffrn_reflns_theta_max         25.002
_diffrn_reflns_theta_min         1.777
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.649
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                1396
_reflns_number_total             2081
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.596
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details 
;
 Flack x determined using 378 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2081
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1053
_refine_ls_R_factor_gt           0.0562
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0140P)²+0.4660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0994
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Riding coordinates:
 N1(H1)
2.b Ternary CH refined with riding coordinates:
 C7(H7)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.7614(3) 0.45786(8) 0.97654(4) 0.0504(3) Uani 1 1 d . . . . .
O1 O 0.7013(15) 0.4878(5) 0.7385(3) 0.0385(16) Uani 1 1 d . . . . .
O2 O 0.9717(12) 0.4276(5) 0.6642(2) 0.0330(15) Uani 1 1 d . . . . .
N1 N 1.1183(15) 0.2326(7) 0.7252(3) 0.0339(19) Uani 1 1 d . . . . .
H1 H 1.2095 0.1805 0.7452 0.041 Uiso 1 1 d R . . . .
C1 C 0.8928(19) 0.3828(9) 0.8611(4) 0.040(3) Uani 1 1 d . . . . .
H1A H 1.0077 0.4514 0.8584 0.048 Uiso 1 1 calc R . . . .
C2 C 0.736(3) 0.3574(7) 0.9117(3) 0.038(2) Uani 1 1 d . . . . .
C3 C 0.567(2) 0.2573(9) 0.9162(4) 0.041(2) Uani 1 1 d . . . . .
H3 H 0.4595 0.2405 0.9511 0.049 Uiso 1 1 calc R . . . .
C4 C 0.556(2) 0.1836(9) 0.8703(4) 0.040(3) Uani 1 1 d . . . . .
H4 H 0.4410 0.1150 0.8731 0.048 Uiso 1 1 calc R . . . .
C5 C 0.711(2) 0.2085(7) 0.8195(4) 0.032(2) Uani 1 1 d . . . . .
H5 H 0.7014 0.1566 0.7876 0.039 Uiso 1 1 calc R . . . .
C6 C 0.8811(18) 0.3071(8) 0.8142(4) 0.030(2) Uani 1 1 d . . . . .
C7 C 1.0571(18) 0.3352(7) 0.7596(4) 0.029(2) Uani 1 1 d . . . . .
H7 H 1.2549 0.3698 0.7713 0.035 Uiso 1 1 calc R . . . .
C8 C 0.889(2) 0.4214(8) 0.7212(4) 0.033(2) Uani 1 1 d . . . . .
C9 C 1.1911(19) 0.3509(7) 0.6416(4) 0.030(2) Uani 1 1 d . . . . .
C10 C 1.259(3) 0.2533(7) 0.6717(3) 0.0300(18) Uani 1 1 d . . . . .
C11 C 1.468(2) 0.1772(8) 0.6465(4) 0.037(2) Uani 1 1 d . . . . .
H11 H 1.5284 0.1100 0.6668 0.044 Uiso 1 1 calc R . . . .
C12 C 1.585(2) 0.2012(8) 0.5915(4) 0.036(2) Uani 1 1 d . . . . .
H12 H 1.7214 0.1485 0.5739 0.043 Uiso 1 1 calc R . . . .
C13 C 1.5089(19) 0.2988(9) 0.5627(4) 0.035(2) Uani 1 1 d . . . . .
H13 H 1.5950 0.3146 0.5255 0.042 Uiso 1 1 calc R . . . .
C14 C 1.3085(19) 0.3740(8) 0.5870(3) 0.032(2) Uani 1 1 d . . . . .
H14 H 1.2505 0.4414 0.5666 0.038 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 0.0648(6) 0.0514(6) 0.0351(4) -0.0020(5) 0.0001(8) 0.0055(9)
O1 0.037(4) 0.031(3) 0.048(4) 0.002(3) 0.009(3) 0.001(4)
O2 0.030(3) 0.040(4) 0.029(3) 0.004(3) 0.002(3) 0.005(3)
N1 0.029(4) 0.037(5) 0.035(4) 0.008(4) -0.006(3) 0.004(4)
C1 0.025(4) 0.045(7) 0.051(7) 0.014(6) -0.009(5) -0.003(5)
C2 0.034(4) 0.046(6) 0.033(5) -0.004(4) -0.002(6) -0.001(7)
C3 0.040(5) 0.035(6) 0.048(6) 0.013(6) 0.002(5) 0.004(5)
C4 0.035(5) 0.030(6) 0.055(7) 0.001(5) -0.004(5) -0.011(5)
C5 0.027(5) 0.031(5) 0.038(5) 0.001(4) -0.010(5) -0.008(5)
C6 0.026(5) 0.040(6) 0.024(5) -0.007(5) -0.005(4) 0.010(5)
C7 0.021(5) 0.029(6) 0.036(6) -0.002(5) -0.001(4) -0.003(4)
C8 0.032(5) 0.031(6) 0.035(6) 0.002(5) -0.004(4) -0.010(5)
C9 0.026(6) 0.031(5) 0.034(5) -0.010(4) 0.000(4) 0.002(4)
C10 0.025(4) 0.026(4) 0.038(5) 0.000(4) 0.003(6) -0.006(7)
C11 0.038(5) 0.032(6) 0.041(6) -0.004(5) -0.002(5) -0.004(5)
C12 0.035(5) 0.034(6) 0.040(6) -0.016(5) 0.008(5) -0.003(5)
C13 0.034(5) 0.046(7) 0.025(5) -0.005(5) 0.001(4) -0.005(5)
C14 0.031(6) 0.034(5) 0.031(5) -0.003(4) 0.000(4) -0.002(5)

_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 C2 1.896(8) . ?
O1 C8 1.202(10) . ?
O2 C8 1.358(10) . ?
O2 C9 1.417(9) . ?
N1 H1 0.8600 . ?
N1 C7 1.458(11) . ?
N1 C10 1.394(10) . ?
C1 H1A 0.9500 . ?
C1 C2 1.383(12) . ?
C1 C6 1.391(12) . ?
C2 C3 1.391(13) . ?
C3 H3 0.9500 . ?
C3 C4 1.360(13) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(12) . ?
C5 H5 0.9500 . ?
C5 C6 1.379(12) . ?
C6 C7 1.510(11) . ?
C7 H7 1.0000 . ?
C7 C8 1.529(12) . ?
C9 C10 1.364(11) . ?
C9 C14 1.381(11) . ?
C10 C11 1.407(13) . ?
C11 H11 0.9500 . ?
C11 C12 1.391(12) . ?
C12 H12 0.9500 . ?
C12 C13 1.359(12) . ?
C13 H13 0.9500 . ?
C13 C14 1.366(12) . ?
C14 H14 0.9500 . ?

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
C8 O2 C9 120.2(7) . . ?
C7 N1 H1 112.3 . . ?
C10 N1 H1 112.4 . . ?
C10 N1 C7 114.5(7) . . ?
C2 C1 H1A 120.2 . . ?
C2 C1 C6 119.6(9) . . ?
C6 C1 H1A 120.2 . . ?
C1 C2 Br1 119.7(7) . . ?
C1 C2 C3 120.7(9) . . ?
C3 C2 Br1 119.5(7) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.5(9) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.1(9) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.3(9) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C7 118.9(8) . . ?
C5 C6 C1 118.8(8) . . ?
C5 C6 C7 122.2(8) . . ?
N1 C7 C6 111.4(7) . . ?
N1 C7 H7 108.3 . . ?
N1 C7 C8 108.7(7) . . ?
C6 C7 H7 108.3 . . ?
C6 C7 C8 111.7(7) . . ?
C8 C7 H7 108.3 . . ?
O1 C8 O2 118.0(8) . . ?
O1 C8 C7 124.7(8) . . ?
O2 C8 C7 117.2(8) . . ?
C10 C9 O2 119.4(8) . . ?
C10 C9 C14 122.6(8) . . ?
C14 C9 O2 117.7(8) . . ?
N1 C10 C11 123.0(8) . . ?
C9 C10 N1 119.5(9) . . ?
C9 C10 C11 117.5(8) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.4(9) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.1(9) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.1(9) . . ?
C14 C13 H13 120.0 . . ?
C9 C14 H14 120.4 . . ?
C13 C14 C9 119.2(8) . . ?
C13 C14 H14 120.4 . . ?

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
Br1 C2 C3 C4 -178.1(8) . . . . ?
O2 C9 C10 N1 -2.2(13) . . . . ?
O2 C9 C10 C11 177.3(8) . . . . ?
O2 C9 C14 C13 -176.7(7) . . . . ?
N1 C7 C8 O1 147.1(8) . . . . ?
N1 C7 C8 O2 -37.2(9) . . . . ?
N1 C10 C11 C12 176.6(8) . . . . ?
C1 C2 C3 C4 0.0(15) . . . . ?
C1 C6 C7 N1 157.7(8) . . . . ?
C1 C6 C7 C8 -80.6(9) . . . . ?
C2 C1 C6 C5 0.2(13) . . . . ?
C2 C1 C6 C7 -179.1(8) . . . . ?
C2 C3 C4 C5 -0.2(15) . . . . ?
C3 C4 C5 C6 0.3(15) . . . . ?
C4 C5 C6 C1 -0.3(14) . . . . ?
C4 C5 C6 C7 179.0(8) . . . . ?
C5 C6 C7 N1 -21.6(11) . . . . ?
C5 C6 C7 C8 100.1(10) . . . . ?
C6 C1 C2 Br1 178.0(7) . . . . ?
C6 C1 C2 C3 -0.1(14) . . . . ?
C6 C7 C8 O1 23.8(11) . . . . ?
C6 C7 C8 O2 -160.5(7) . . . . ?
C7 N1 C10 C9 -34.0(12) . . . . ?
C7 N1 C10 C11 146.5(8) . . . . ?
C8 O2 C9 C10 17.4(11) . . . . ?
C8 O2 C9 C14 -168.2(7) . . . . ?
C9 O2 C8 O1 -179.8(7) . . . . ?
C9 O2 C8 C7 4.2(10) . . . . ?
C9 C10 C11 C12 -2.9(13) . . . . ?
C10 N1 C7 C6 175.0(7) . . . . ?
C10 N1 C7 C8 51.6(10) . . . . ?
C10 C9 C14 C13 -2.5(13) . . . . ?
C10 C11 C12 C13 2.2(13) . . . . ?
C11 C12 C13 C14 -1.4(13) . . . . ?
C12 C13 C14 C9 1.5(13) . . . . ?
C14 C9 C10 N1 -176.4(8) . . . . ?
C14 C9 C10 C11 3.1(14) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'

