# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_20180321-1
_database_code_depnum_ccdc_archive 'CCDC 1834083'
_audit_update_record             
;
2018-04-02 deposited with the CCDC.
2018-05-30 downloaded from the CCDC.
;
_audit_creation_date             2018-03-22
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.01.22 svn.r3481 for OlexSys, GUI svn.r5457)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '0.17(Br C15 O2)'
_chemical_formula_sum            'C H Br0 N O'
_chemical_formula_weight         43.03
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
_chemical_oxdiff_usercomment     'C H N S Ni'
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'
Br Br -0.6763 1.2805 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   7.8543(5)
_cell_length_b                   20.6582(9)
_cell_length_c                   8.3912(5)
_cell_angle_alpha                90
_cell_angle_beta                 116.689(8)
_cell_angle_gamma                90
_cell_volume                     1216.46(14)
_cell_formula_units_Z            23
_cell_measurement_reflns_used    2364
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.2080
_cell_measurement_theta_min      4.3140
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             506
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0138
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4094
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.090
_diffrn_reflns_theta_min         4.280
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0802
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):
  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     49.00  97.00   1.00   11.23    --   35.96  57.00   0.00   48
  2  ω     65.00 106.00   1.00   11.23    --   35.96 178.00 -30.00   41
  3  ω     65.00  93.00   1.00   11.23    --   35.96-178.00 120.00   28
  4  ω    -15.00  12.00   1.00   11.23    --   35.96 -77.00 150.00   27
  5  ω     17.00  62.00   1.00   11.23    --   35.96 -77.00 150.00   45
  6  ω     26.00  73.00   1.00   11.23    --   35.96  57.00 -30.00   47
  7  ω     -7.00  55.00   1.00   11.23    --   35.96 -38.00  30.00   62
  8  ω     39.00  94.00   1.00   44.92    --  108.00 -95.00-180.00   55
  9  ω    108.00 176.00   1.00   44.92    --  108.00  45.00 -60.00   68
 10  ω     64.00 115.00   1.00   44.92    --  108.00 -77.00 -90.00   51
 11  ω     93.00 126.00   1.00   44.92    --  108.00  61.00 -90.00   33
 12  ω     90.00 144.00   1.00   44.92    --  108.00  61.00-180.00   54
 13  ω     96.00 175.00   1.00   44.92    --  108.00  61.00  30.00   79
 14  ω     51.00  88.00   1.00   44.92    --  108.00 -95.00 -90.00   37
 15  ω     65.00 137.00   1.00   44.92    --  108.00 178.00-150.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0177471000
_diffrn_orient_matrix_UB_12      -0.0700110000
_diffrn_orient_matrix_UB_13      0.0690406000
_diffrn_orient_matrix_UB_21      -0.1838073000
_diffrn_orient_matrix_UB_22      -0.0183964000
_diffrn_orient_matrix_UB_23      -0.1667764000
_diffrn_orient_matrix_UB_31      0.1187694000
_diffrn_orient_matrix_UB_32      -0.0179399000
_diffrn_orient_matrix_UB_33      -0.0980277000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2180
_reflns_number_total             2329
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         7.012
_refine_diff_density_min         -5.863
_refine_diff_density_rms         0.319
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   6.194
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         2329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2157
_refine_ls_R_factor_gt           0.2119
_refine_ls_restrained_S_all      6.194
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.6061
_refine_ls_wR_factor_ref         0.6139
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   .
_atom_sites_solution_primary     dual
_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
Br01 Br 0.6187(3) 0.66451(9) 0.8371(3) 0.0648(11) Uiso 1 1 d . . . . .
O002 O 0.7310(14) 0.5183(5) 0.5728(14) 0.051(2) Uiso 1 1 d . . . . .
O003 O 0.8051(17) 0.4150(6) 0.5685(16) 0.061(3) Uiso 1 1 d . . . . .
C004 C 0.775(2) 0.4562(8) 0.641(2) 0.053(3) Uiso 1 1 d . . . . .
C005 C 0.674(2) 0.7272(8) 0.252(2) 0.054(3) Uiso 1 1 d . . . . .
C006 C 0.821(2) 0.6805(8) 0.325(2) 0.056(3) Uiso 1 1 d . . . . .
C007 C 0.733(2) 0.5148(8) 0.866(2) 0.053(3) Uiso 1 1 d . . . . .
C008 C 0.773(2) 0.4551(8) 0.821(2) 0.060(4) Uiso 1 1 d . . . . .
C009 C 0.805(2) 0.6392(8) 0.448(2) 0.050(3) Uiso 1 1 d . . . . .
C00A C 0.531(2) 0.7305(9) 0.304(2) 0.055(3) Uiso 1 1 d . . . . .
C00B C 0.525(2) 0.6942(9) 0.432(2) 0.059(4) Uiso 1 1 d . . . . .
C00C C 0.666(2) 0.6457(9) 0.511(2) 0.053(3) Uiso 1 1 d . . . . .
C00D C 0.765(2) 0.4707(9) 1.139(2) 0.061(4) Uiso 1 1 d . . . . .
C00E C 0.727(2) 0.5228(9) 1.027(2) 0.059(4) Uiso 1 1 d . . . . .
C00F C 0.810(3) 0.3999(10) 0.925(3) 0.066(4) Uiso 1 1 d . . . . .
C00G C 0.802(3) 0.4102(10) 1.086(3) 0.065(4) Uiso 1 1 d . . . . .
C00H C 0.709(3) 0.5521(10) 0.712(3) 0.066(4) Uiso 1 1 d . . . . .
C00I C 0.664(3) 0.6105(10) 0.668(3) 0.067(4) Uiso 1 1 d . . . . .

_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
Br01 C00I 1.95(2) . ?
O002 C004 1.38(2) . ?
O002 C00H 1.44(2) . ?
O003 C004 1.13(2) . ?
C004 C008 1.51(2) . ?
C005 C006 1.42(2) . ?
C005 C00A 1.37(2) . ?
C006 C009 1.39(2) . ?
C007 C008 1.37(2) . ?
C007 C00E 1.38(2) . ?
C007 C00H 1.44(3) . ?
C008 C00F 1.38(3) . ?
C009 C00C 1.41(2) . ?
C00A C00B 1.33(2) . ?
C00B C00C 1.42(2) . ?
C00C C00I 1.52(3) . ?
C00D C00E 1.37(3) . ?
C00D C00G 1.40(3) . ?
C00F C00G 1.40(3) . ?
C00H C00I 1.26(3) . ?

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
C004 O002 C00H 102.2(13) . . ?
O002 C004 C008 108.4(13) . . ?
O003 C004 O002 123.0(15) . . ?
O003 C004 C008 128.7(16) . . ?
C00A C005 C006 121.4(16) . . ?
C009 C006 C005 114.0(16) . . ?
C008 C007 C00E 119.4(16) . . ?
C008 C007 C00H 100.8(16) . . ?
C00E C007 C00H 139.8(17) . . ?
C007 C008 C004 111.7(15) . . ?
C007 C008 C00F 125.4(18) . . ?
C00F C008 C004 123.0(16) . . ?
C006 C009 C00C 124.3(15) . . ?
C00B C00A C005 124.0(16) . . ?
C00A C00B C00C 118.2(16) . . ?
C009 C00C C00B 117.7(15) . . ?
C009 C00C C00I 126.2(15) . . ?
C00B C00C C00I 115.8(15) . . ?
C00E C00D C00G 119.4(18) . . ?
C00D C00E C007 119.1(17) . . ?
C008 C00F C00G 113.3(19) . . ?
C00F C00G C00D 123.4(19) . . ?
C007 C00H O002 117.0(16) . . ?
C00I C00H O002 110.4(17) . . ?
C00I C00H C007 133(2) . . ?
C00C C00I Br01 115.8(13) . . ?
C00H C00I Br01 117.0(16) . . ?
C00H C00I C00C 126.7(19) . . ?

_iucr_refine_instructions_details 
;

    20180321-1.res created by SHELXL-2014/7

TITL 20180321-1_a.res in P2(1)/n
REM Old TITL 20180321-1 in P21/n #14
REM SHELXT solution in P2(1)/n
REM R1 0.214, Rweak 0.022, Alpha 0.047, Orientation as input
REM Formula found by SHELXT: C15 O2 Br
CELL 1.54184 7.8543 20.6582 8.3912 90 116.689 90
ZERR 23 0.0005 0.0009 0.0005 0 0.008 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N O Br
UNIT 23 23 23 23 0
 
L.S. 10
PLAN  20
BOND $H
list 4
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\20180321-1.hkl">
REM </olex2.extras>
 
WGHT    0.100000
FVAR       0.60427
BR01  5    0.618665    0.664510    0.837060    11.00000    0.06481
O002  4    0.731040    0.518266    0.572845    11.00000    0.05091
O003  4    0.805123    0.415032    0.568458    11.00000    0.06060
C004  1    0.774919    0.456194    0.641385    11.00000    0.05252
C005  1    0.673594    0.727175    0.251586    11.00000    0.05427
C006  1    0.821333    0.680518    0.324816    11.00000    0.05640
C007  1    0.732838    0.514834    0.866056    11.00000    0.05333
C008  1    0.772633    0.455094    0.820766    11.00000    0.05958
C009  1    0.804521    0.639216    0.448216    11.00000    0.04951
C00A  1    0.531115    0.730467    0.303615    11.00000    0.05549
C00B  1    0.524953    0.694187    0.431623    11.00000    0.05858
C00C  1    0.665724    0.645728    0.510607    11.00000    0.05336
C00D  1    0.765375    0.470696    1.139262    11.00000    0.06122
C00E  1    0.727499    0.522819    1.026860    11.00000    0.05903
C00F  1    0.810344    0.399934    0.924667    11.00000    0.06604
C00G  1    0.802458    0.410184    1.085816    11.00000    0.06510
C00H  1    0.709270    0.552136    0.712367    11.00000    0.06581
C00I  1    0.663558    0.610514    0.668500    11.00000    0.06699
HKLF 4
 
REM  20180321-1_a.res in P2(1)/n
REM R1 =  0.2119 for    2180 Fo > 4sig(Fo)  and  0.2157 for all    2329 data
REM     73 parameters refined using      0 restraints
 
END  
     
WGHT      0.2000      0.0000 

REM Highest difference peak  7.012,  deepest hole -5.863,  1-sigma level  0.319
Q1    1   0.5419  0.6651  0.7819  11.00000  0.05    6.93
Q2    1   0.6927  0.5804  0.6059  11.00000  0.05    2.13
Q3    1   0.6758  0.5816  0.7662  11.00000  0.05    2.07
Q4    1   0.7553  0.4864  0.8373  11.00000  0.05    1.16
Q5    1   0.7807  0.4371  1.1213  11.00000  0.05    1.15
Q6    1   0.7020  0.5547  1.0575  11.00000  0.05    1.00
Q7    1   0.6967  0.6263  0.4672  11.00000  0.05    0.98
Q8    1   0.5955  0.7238  0.2096  11.00000  0.05    0.84
Q9    1   0.5301  0.6653  0.4300  11.00000  0.05    0.76
Q10   1   0.8025  0.4228  0.9548  11.00000  0.05    0.69
Q11   1   0.9170  0.6064  0.4836  11.00000  0.05    0.67
Q12   1   0.6762  0.7431  0.1355  11.00000  0.05    0.66
Q13   1   0.7795  0.3329  0.4620  11.00000  0.05    0.63
Q14   1   0.4014  0.6949  0.4572  11.00000  0.05    0.63
Q15   1   0.8973  0.6713  0.2608  11.00000  0.05    0.61
Q16   1   0.8369  0.3645  0.8864  11.00000  0.05    0.60
Q17   1   0.5796  0.6927  0.9411  11.00000  0.05    0.58
Q18   1   0.3934  0.6728  0.7754  11.00000  0.05    0.55
Q19   1   0.6993  0.7672  0.1980  11.00000  0.05    0.52
Q20   1   0.7036  0.6440  0.7583  11.00000  0.05    0.51

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.2119 for 2180 Fo > 4sig(Fo) and 0.2157 for all 4189 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 7.01, deepest hole -5.86
  REM Mean Shift 0, Max Shift -0.002.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.2157
  REM R1_gt = 0.2119
  REM wR_ref = 0.6139
  REM GOOF = 6.194
  REM Shift_max = -0.002
  REM Shift_mean = 0
  REM Reflections_all = 4189
  REM Reflections_gt = 2180
  REM Parameters = n/a
  REM Hole = -5.86
  REM Peak = 7.01
  REM Flack = n/a

  
;
_olex2_date_sample_data_collection 2018-03-21
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.539
_oxdiff_exptl_absorpt_empirical_full_min 0.681
