# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_exp_442mb2
_database_code_depnum_ccdc_archive 'CCDC 1551595'
_audit_update_record             
;
2017-05-22 deposited with the CCDC.
2017-06-21 downloaded from the CCDC.
;
_audit_creation_date             2017-05-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'0.8(Br), 0.4(C13 H30 N2 O2), 0.4(C H4 O), 0.2(C O)'
_chemical_formula_sum            'C11 H10 Br0 N O'
_chemical_formula_weight         172.20
_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 0.0181 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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1520(7)
_cell_length_b                   8.1484(6)
_cell_length_c                   20.7756(9)
_cell_angle_alpha                90.232(5)
_cell_angle_beta                 98.462(6)
_cell_angle_gamma                113.488(9)
_cell_volume                     1095.71(16)
_cell_formula_units_Z            5
_cell_measurement_reflns_used    4079
_cell_measurement_temperature    105(8)
_cell_measurement_theta_max      70.8400
_cell_measurement_theta_min      5.9360
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.672
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61245
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             455
_exptl_crystal_size_max          0.2
_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  0.0398
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.774
_diffrn_reflns_Laue_measured_fraction_max 0.744
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            5665
_diffrn_reflns_point_group_measured_fraction_full 0.774
_diffrn_reflns_point_group_measured_fraction_max 0.744
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.241
_diffrn_reflns_theta_min         4.313
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      105(8)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0509
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.774
_diffrn_measured_fraction_theta_max 0.744
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -22.00  69.00   1.00   10.00    --    0.00  57.00  90.00   91
  2  ω   -127.00 -80.00   1.00   10.00    --  -54.31 -95.00  90.00   47
  3  ω   -126.00 -73.00   1.00   10.00    --  -54.31-125.00 150.00   53
  4  ω   -127.00 -80.00   1.00   10.00    --  -54.31 -95.00 -90.00   47
  5  ω     20.00 128.00   1.00   10.00    --   54.31  30.00 150.00  108
  6  ω    100.00 178.00   1.00   10.00    --  108.61 111.00  60.00   78
  7  ω     84.00 177.00   1.00   10.00    --  108.61  64.00-120.00   93
  8  ω     77.00 178.00   1.00   10.00    --  108.61  77.00 120.00  101
  9  ω     85.00 178.00   1.00   10.00    --  108.61  50.00 150.00   93
 10  ω    -22.00  69.00   1.00   10.00    --    0.00  57.00  30.00   91
 11  ω   -125.00 -23.00   1.00   10.00    --  -54.31 -77.00  30.00  102
 12  ω   -122.00 -31.00   1.00   10.00    --  -54.31 -61.00 -30.00   91
 13  ω     23.00 125.00   1.00   10.00    --   54.31  77.00-180.00  102
 14  ω     23.00 125.00   1.00   10.00    --   54.31  77.00-120.00  102
 15  ω     23.00 112.00   1.00   10.00    --   54.31-125.00-150.00   89
 16  ω     84.00 177.00   1.00   10.00    --  108.61  64.00 -30.00   93
 17  ω     35.00  60.00   1.00   10.00    --  108.61-111.00  90.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1418316000
_diffrn_orient_matrix_UB_12      0.1019185000
_diffrn_orient_matrix_UB_13      -0.0102354000
_diffrn_orient_matrix_UB_21      0.0167473000
_diffrn_orient_matrix_UB_22      0.0258838000
_diffrn_orient_matrix_UB_23      0.0744405000
_diffrn_orient_matrix_UB_31      0.1904051000
_diffrn_orient_matrix_UB_32      0.1778821000
_diffrn_orient_matrix_UB_33      0.0010666000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2767
_reflns_number_total             3160
_reflns_odcompleteness_completeness 77.86
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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         2.238
_refine_diff_density_min         -1.204
_refine_diff_density_rms         0.272
_refine_ls_extinction_coef       0.0001(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.440
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     207
_refine_ls_number_reflns         3160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0907
_refine_ls_restrained_S_all      1.440
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3108
_refine_ls_wR_factor_ref         0.3187
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: O0AA(0.5) C2(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C00A(H00J,H00K), C00E(H00O,H00P), C00F(H00Q,H00R), C00G(H00S,H00T), C00H(H00U,
 H00V), C00I(H00W,H00X), C00J(H00Y,H)
3.b Idealised Me refined as rotating group:
 C007(H00A,H00B,H00C), C008(H00D,H00E,H00F), C009(H00G,H00H,H00I), C00D(H00L,
 H00M,H00N), C00K(H00Z,HA,HB), C1(H1A,H1B,H1C)
3.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_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
Br1 Br -0.35334(13) 0.24929(11) 0.39529(4) 0.0284(5) Uani 1 1 d . . . . .
Br2 Br 0.20277(14) 0.35946(12) 0.76819(4) 0.0332(5) Uani 1 1 d . . . . .
O2 O -0.0040(9) 0.1397(8) 0.5484(2) 0.0268(13) Uani 1 1 d . . . . .
O1 O 0.0988(10) 0.3244(8) 0.4689(3) 0.0307(14) Uani 1 1 d . . . . .
H1 H -0.0257 0.2904 0.4563 0.046 Uiso 1 1 calc GR . . . .
N1 N 0.6061(11) 0.3089(9) 0.6496(3) 0.0206(15) Uani 1 1 d . . . . .
N2 N 0.9275(10) 0.7881(9) 0.7293(3) 0.0208(15) Uani 1 1 d . . . . .
C007 C 0.7522(13) 0.2827(11) 0.6087(3) 0.0223(17) Uani 1 1 d . . . . .
H00A H 0.7005 0.1587 0.5935 0.033 Uiso 1 1 calc GR . . . .
H00B H 0.8863 0.3175 0.6347 0.033 Uiso 1 1 calc GR . . . .
H00C H 0.7623 0.3551 0.5720 0.033 Uiso 1 1 calc GR . . . .
C008 C 0.7702(13) 0.8104(11) 0.7661(4) 0.0237(18) Uani 1 1 d . . . . .
H00D H 0.8209 0.9324 0.7835 0.036 Uiso 1 1 calc GR . . . .
H00E H 0.7477 0.7319 0.8011 0.036 Uiso 1 1 calc GR . . . .
H00F H 0.6424 0.7811 0.7369 0.036 Uiso 1 1 calc GR . . . .
C009 C 0.9402(14) 0.8940(11) 0.6697(4) 0.027(2) Uani 1 1 d . . . . .
H00G H 0.8057 0.8543 0.6436 0.041 Uiso 1 1 calc GR . . . .
H00H H 1.0341 0.8760 0.6448 0.041 Uiso 1 1 calc GR . . . .
H00I H 0.9889 1.0191 0.6828 0.041 Uiso 1 1 calc GR . . . .
C00A C 0.3869(13) 0.2302(11) 0.6130(4) 0.0231(18) Uani 1 1 d . . . . .
H00J H 0.2975 0.2499 0.6401 0.028 Uiso 1 1 calc R . . . .
H00K H 0.3432 0.1016 0.6059 0.028 Uiso 1 1 calc R . . . .
C00B C 0.1307(14) 0.2429(11) 0.5225(3) 0.0223(18) Uani 1 1 d . . . . .
C00D C 0.6055(15) 0.2054(11) 0.7093(4) 0.0264(19) Uani 1 1 d . . . . .
H00L H 0.5583 0.0803 0.6965 0.040 Uiso 1 1 calc GR . . . .
H00M H 0.5150 0.2220 0.7361 0.040 Uiso 1 1 calc GR . . . .
H00N H 0.7430 0.2479 0.7336 0.040 Uiso 1 1 calc GR . . . .
C00E C 0.8711(12) 0.5926(10) 0.7115(3) 0.0215(17) Uani 1 1 d . . . . .
H00O H 0.8683 0.5296 0.7511 0.026 Uiso 1 1 calc R . . . .
H00P H 0.9768 0.5821 0.6895 0.026 Uiso 1 1 calc R . . . .
C00F C 0.6620(12) 0.5037(10) 0.6676(3) 0.0218(17) Uani 1 1 d . . . . .
H00Q H 0.5563 0.5138 0.6897 0.026 Uiso 1 1 calc R . . . .
H00R H 0.6646 0.5670 0.6280 0.026 Uiso 1 1 calc R . . . .
C00G C 0.3562(13) 0.3064(11) 0.5473(3) 0.0226(18) Uani 1 1 d . . . . .
H00S H 0.4191 0.4364 0.5521 0.027 Uiso 1 1 calc R . . . .
H00T H 0.4220 0.2671 0.5164 0.027 Uiso 1 1 calc R . . . .
C00H C 1.1555(14) 0.7846(11) 0.8376(4) 0.030(2) Uani 1 1 d . . . . .
H00U H 1.0715 0.8150 0.8641 0.036 Uiso 1 1 calc R . . . .
H00V H 1.1039 0.6550 0.8322 0.036 Uiso 1 1 calc R . . . .
C00I C 1.1424(14) 0.8616(11) 0.7714(3) 0.0256(18) Uani 1 1 d . . . . .
H00W H 1.2368 0.8387 0.7472 0.031 Uiso 1 1 calc R . . . .
H00X H 1.1898 0.9906 0.7782 0.031 Uiso 1 1 calc R . . . .
C00J C 1.3788(16) 0.8620(15) 0.8708(4) 0.045(2) Uani 1 1 d . . . . .
H00Y H 1.4305 0.9918 0.8733 0.054 Uiso 1 1 calc R . . . .
H H 1.4598 0.8275 0.8442 0.054 Uiso 1 1 calc R . . . .
C00K C 1.410(2) 0.8003(16) 0.9395(5) 0.059(3) Uani 1 1 d . . . . .
H00Z H 1.3111 0.6795 0.9412 0.088 Uiso 1 1 calc GR . . . .
HA H 1.3903 0.8778 0.9703 0.088 Uiso 1 1 calc GR . . . .
HB H 1.5470 0.8048 0.9499 0.088 Uiso 1 1 calc GR . . . .
O3 O 0.6668(13) 0.4453(14) 0.8503(3) 0.070(3) Uani 1 1 d . . . . .
H3 H 0.5469 0.4235 0.8344 0.105 Uiso 1 1 calc GR . . . .
C1 C 0.691(2) 0.473(2) 0.9141(6) 0.084(5) Uani 1 1 d . . . . .
H1A H 0.6717 0.5797 0.9242 0.126 Uiso 1 1 calc GR . . . .
H1B H 0.8272 0.4868 0.9332 0.126 Uiso 1 1 calc GR . . . .
H1C H 0.5905 0.3724 0.9313 0.126 Uiso 1 1 calc GR . . . .
O0AA O 1.023(4) 0.182(3) 0.9337(11) 0.100(6) Uiso 0.5 1 d . . P . .
C2 C 1.109(4) 0.140(3) 0.9010(10) 0.053(5) Uiso 0.5 1 d . . P . .


_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
O2 C00B 1.199(10) . ?
O1 H1 0.8200 . ?
O1 C00B 1.337(9) . ?
N1 C007 1.515(9) . ?
N1 C00A 1.514(11) . ?
N1 C00D 1.503(9) . ?
N1 C00F 1.505(10) . ?
N2 C008 1.516(10) . ?
N2 C009 1.506(8) . ?
N2 C00E 1.508(9) . ?
N2 C00I 1.534(10) . ?
C007 H00A 0.9600 . ?
C007 H00B 0.9600 . ?
C007 H00C 0.9600 . ?
C008 H00D 0.9600 . ?
C008 H00E 0.9600 . ?
C008 H00F 0.9600 . ?
C009 H00G 0.9600 . ?
C009 H00H 0.9600 . ?
C009 H00I 0.9600 . ?
C00A H00J 0.9700 . ?
C00A H00K 0.9700 . ?
C00A C00G 1.524(10) . ?
C00B C00G 1.491(12) . ?
C00D H00L 0.9600 . ?
C00D H00M 0.9600 . ?
C00D H00N 0.9600 . ?
C00E H00O 0.9700 . ?
C00E H00P 0.9700 . ?
C00E C00F 1.525(12) . ?
C00F H00Q 0.9700 . ?
C00F H00R 0.9700 . ?
C00G H00S 0.9700 . ?
C00G H00T 0.9700 . ?
C00H H00U 0.9700 . ?
C00H H00V 0.9700 . ?
C00H C00I 1.519(9) . ?
C00H C00J 1.514(12) . ?
C00I H00W 0.9700 . ?
C00I H00X 0.9700 . ?
C00J H00Y 0.9700 . ?
C00J H 0.9700 . ?
C00J C00K 1.530(12) . ?
C00K H00Z 0.9600 . ?
C00K HA 0.9600 . ?
C00K HB 0.9600 . ?
O3 H3 0.8200 . ?
O3 C1 1.317(13) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
O0AA C2 1.12(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
C00B O1 H1 109.5 . . ?
C00A N1 C007 110.5(6) . . ?
C00D N1 C007 108.4(5) . . ?
C00D N1 C00A 106.3(6) . . ?
C00D N1 C00F 111.3(6) . . ?
C00F N1 C007 112.4(6) . . ?
C00F N1 C00A 107.8(5) . . ?
C008 N2 C00I 110.8(6) . . ?
C009 N2 C008 108.6(6) . . ?
C009 N2 C00E 111.5(6) . . ?
C009 N2 C00I 107.8(6) . . ?
C00E N2 C008 110.9(6) . . ?
C00E N2 C00I 107.2(5) . . ?
N1 C007 H00A 109.5 . . ?
N1 C007 H00B 109.5 . . ?
N1 C007 H00C 109.5 . . ?
H00A C007 H00B 109.5 . . ?
H00A C007 H00C 109.5 . . ?
H00B C007 H00C 109.5 . . ?
N2 C008 H00D 109.5 . . ?
N2 C008 H00E 109.5 . . ?
N2 C008 H00F 109.5 . . ?
H00D C008 H00E 109.5 . . ?
H00D C008 H00F 109.5 . . ?
H00E C008 H00F 109.5 . . ?
N2 C009 H00G 109.5 . . ?
N2 C009 H00H 109.5 . . ?
N2 C009 H00I 109.5 . . ?
H00G C009 H00H 109.5 . . ?
H00G C009 H00I 109.5 . . ?
H00H C009 H00I 109.5 . . ?
N1 C00A H00J 108.5 . . ?
N1 C00A H00K 108.5 . . ?
N1 C00A C00G 115.0(6) . . ?
H00J C00A H00K 107.5 . . ?
C00G C00A H00J 108.5 . . ?
C00G C00A H00K 108.5 . . ?
O2 C00B O1 124.4(8) . . ?
O2 C00B C00G 125.1(7) . . ?
O1 C00B C00G 110.4(7) . . ?
N1 C00D H00L 109.5 . . ?
N1 C00D H00M 109.5 . . ?
N1 C00D H00N 109.5 . . ?
H00L C00D H00M 109.5 . . ?
H00L C00D H00N 109.5 . . ?
H00M C00D H00N 109.5 . . ?
N2 C00E H00O 109.1 . . ?
N2 C00E H00P 109.1 . . ?
N2 C00E C00F 112.6(6) . . ?
H00O C00E H00P 107.8 . . ?
C00F C00E H00O 109.1 . . ?
C00F C00E H00P 109.1 . . ?
N1 C00F C00E 112.6(6) . . ?
N1 C00F H00Q 109.1 . . ?
N1 C00F H00R 109.1 . . ?
C00E C00F H00Q 109.1 . . ?
C00E C00F H00R 109.1 . . ?
H00Q C00F H00R 107.8 . . ?
C00A C00G H00S 109.8 . . ?
C00A C00G H00T 109.8 . . ?
C00B C00G C00A 109.2(6) . . ?
C00B C00G H00S 109.8 . . ?
C00B C00G H00T 109.8 . . ?
H00S C00G H00T 108.3 . . ?
H00U C00H H00V 108.3 . . ?
C00I C00H H00U 109.9 . . ?
C00I C00H H00V 109.9 . . ?
C00J C00H H00U 109.9 . . ?
C00J C00H H00V 109.9 . . ?
C00J C00H C00I 108.9(7) . . ?
N2 C00I H00W 108.4 . . ?
N2 C00I H00X 108.4 . . ?
C00H C00I N2 115.6(7) . . ?
C00H C00I H00W 108.4 . . ?
C00H C00I H00X 108.4 . . ?
H00W C00I H00X 107.4 . . ?
C00H C00J H00Y 108.9 . . ?
C00H C00J H 108.9 . . ?
C00H C00J C00K 113.5(9) . . ?
H00Y C00J H 107.7 . . ?
C00K C00J H00Y 108.9 . . ?
C00K C00J H 108.9 . . ?
C00J C00K H00Z 109.5 . . ?
C00J C00K HA 109.5 . . ?
C00J C00K HB 109.5 . . ?
H00Z C00K HA 109.5 . . ?
H00Z C00K HB 109.5 . . ?
HA C00K HB 109.5 . . ?
C1 O3 H3 109.5 . . ?
O3 C1 H1A 109.5 . . ?
O3 C1 H1B 109.5 . . ?
O3 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 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
O2 C00B C00G C00A -4.1(11) . . . . ?
O1 C00B C00G C00A 172.7(6) . . . . ?
N1 C00A C00G C00B -169.7(6) . . . . ?
N2 C00E C00F N1 179.8(5) . . . . ?
C007 N1 C00A C00G -57.8(8) . . . . ?
C007 N1 C00F C00E -64.6(8) . . . . ?
C008 N2 C00E C00F 60.7(8) . . . . ?
C008 N2 C00I C00H 55.0(8) . . . . ?
C009 N2 C00E C00F -60.4(8) . . . . ?
C009 N2 C00I C00H 173.7(6) . . . . ?
C00A N1 C00F C00E 173.4(6) . . . . ?
C00D N1 C00A C00G -175.2(6) . . . . ?
C00D N1 C00F C00E 57.2(8) . . . . ?
C00E N2 C00I C00H -66.2(8) . . . . ?
C00F N1 C00A C00G 65.3(8) . . . . ?
C00I N2 C00E C00F -178.2(6) . . . . ?
C00I C00H C00J C00K 177.4(8) . . . . ?
C00J C00H C00I N2 176.4(7) . . . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.971
_oxdiff_exptl_absorpt_empirical_full_min 0.510
_chemical_properties_physical    ', Moisture-sensitive,Hygroscopic'
####################################################################### 
# 
# 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_exp_327pia1
_database_code_depnum_ccdc_archive 'CCDC 1551600'
_audit_update_record             
;
2017-05-22 deposited with the CCDC.
2017-06-21 downloaded from the CCDC.
;
_audit_creation_date             2017-05-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         
'0.13(Br), 0.13(C11 H27 N2 O3 S), 0.13(H2 O), 0.03(H2 O2), 0.06(H0.77 O0.26)'
_chemical_formula_sum            'C H Br0 Cl0.02 N O S0.02'
_chemical_formula_weight         44.12
_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 0.0181 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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   24.0379(3)
_cell_length_b                   8.61570(10)
_cell_length_c                   16.3926(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.7000(10)
_cell_angle_gamma                90.00
_cell_volume                     3346.43(7)
_cell_formula_units_Z            62
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    1.387
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1397
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            30205
_diffrn_reflns_theta_full        73.39
_diffrn_reflns_theta_max         73.39
_diffrn_reflns_theta_min         5.46
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3319
_reflns_number_total             3322
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.643
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         3322
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0326
_refine_ls_restrained_S_all      1.182
_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)+(0.0334P)²+11.1108P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0809
_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:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Others
 Fixed Sof: H00(0.5)
3.a Free rotating group:
 O003(H00Z,H), O00(H00), O1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00B(H00C,H00D), C00C(H00E,H00F), C00D(H00G,H00H), C00F(H00L,
 H00M), C00G(H00N,H00O)
3.c Idealised Me refined as rotating group:
 C00E(H00I,H00J,H00K), C00H(H00P,H00Q,H00R), C00I(H00S,H00T,H00U), C00J(H00V,
 H00W,H00X), C00K(H00Y,HA,HB)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Br01 Br 0.444656(10) 0.82669(3) 0.415655(14) 0.01617(9) Uani 1 d . . 1 . . .
S002 S 0.26540(2) 0.50440(6) 0.16432(3) 0.01201(13) Uani 1 d . . 1 . . .
O003 O 0.42307(7) 0.6004(2) 0.25169(11) 0.0216(4) Uani 1 d . . 1 . . .
H00Z H 0.3883 0.5762 0.2454 0.032 Uiso 1 d . . 1 G . .
H H 0.4314 0.6582 0.2940 0.032 Uiso 1 d . . 1 G . .
O7 O 0.24393(7) 0.65118(19) 0.12736(10) 0.0161(3) Uani 1 d . . 1 . . .
O005 O 0.31158(7) 0.5267(2) 0.23392(11) 0.0219(4) Uani 1 d . . 1 . . .
O006 O 0.27933(8) 0.3946(2) 0.10330(11) 0.0218(4) Uani 1 d . . 1 . . .
N007 N 0.11244(8) 0.1066(2) 0.51070(11) 0.0121(4) Uani 1 d . . 1 . . .
N008 N 0.13087(8) 0.4853(2) 0.39094(12) 0.0138(4) Uani 1 d . . 1 . . .
O00 O 0.5000 0.3608(4) 0.2500 0.0403(8) Uani 1 d . . 2 S T P
H00 H 0.4732 0.4253 0.2492 0.060 Uiso 0.50 d . . 1 G . .
C00A C 0.10046(10) 0.3610(3) 0.43183(15) 0.0145(5) Uani 1 d . . 1 . . .
H00A H 0.0742 0.3070 0.3899 0.017 Uiso 1 calc . . 1 R . .
H00B H 0.0789 0.4094 0.4699 0.017 Uiso 1 calc . . 1 R . .
C00B C 0.19464(9) 0.5128(3) 0.28013(14) 0.0125(4) Uani 1 d . . 1 . . .
H00C H 0.2280 0.5348 0.3206 0.015 Uiso 1 calc . . 1 R . .
H00D H 0.1772 0.6103 0.2603 0.015 Uiso 1 calc . . 1 R . .
C00C C 0.07003(10) 0.1547(3) 0.56507(15) 0.0158(5) Uani 1 d . . 1 . . .
H00E H 0.0397 0.2119 0.5315 0.019 Uiso 1 calc . . 1 R . .
H00F H 0.0537 0.0619 0.5849 0.019 Uiso 1 calc . . 1 R . .
C00D C 0.14172(9) 0.2437(3) 0.47900(14) 0.0124(4) Uani 1 d . . 1 . . .
H00G H 0.1668 0.2065 0.4427 0.015 Uiso 1 calc . . 1 R . .
H00H H 0.1646 0.2956 0.5255 0.015 Uiso 1 calc . . 1 R . .
C00E C 0.15780(10) 0.0069(3) 0.55890(15) 0.0158(5) Uani 1 d . . 1 . . .
H00I H 0.1793 0.0672 0.6024 0.024 Uiso 1 calc . . 1 GR . .
H00J H 0.1823 -0.0307 0.5227 0.024 Uiso 1 calc . . 1 GR . .
H00K H 0.1408 -0.0794 0.5824 0.024 Uiso 1 calc . . 1 GR . .
C00F C 0.21020(10) 0.4186(3) 0.20810(14) 0.0135(4) Uani 1 d . . 1 . . .
H00L H 0.1771 0.4083 0.1655 0.016 Uiso 1 calc . . 1 R . .
H00M H 0.2216 0.3152 0.2276 0.016 Uiso 1 calc . . 1 R . .
C00G C 0.15351(10) 0.4142(3) 0.31839(14) 0.0134(4) Uani 1 d . . 1 . . .
H00N H 0.1720 0.3172 0.3366 0.016 Uiso 1 calc . . 1 R . .
H00O H 0.1217 0.3894 0.2756 0.016 Uiso 1 calc . . 1 R . .
C00H C 0.08193(11) 0.0118(3) 0.44011(15) 0.0197(5) Uani 1 d . . 1 . . .
H00P H 0.0669 -0.0801 0.4614 0.030 Uiso 1 calc . . 1 GR . .
H00Q H 0.1077 -0.0169 0.4039 0.030 Uiso 1 calc . . 1 GR . .
H00R H 0.0516 0.0719 0.4099 0.030 Uiso 1 calc . . 1 GR . .
C00I C 0.09441(11) 0.2532(3) 0.63859(15) 0.0193(5) Uani 1 d . . 1 . . .
H00S H 0.1096 0.3471 0.6197 0.029 Uiso 1 calc . . 1 GR . .
H00T H 0.1239 0.1968 0.6730 0.029 Uiso 1 calc . . 1 GR . .
H00U H 0.0653 0.2783 0.6699 0.029 Uiso 1 calc . . 1 GR . .
C00J C 0.17659(11) 0.5576(3) 0.45281(15) 0.0206(5) Uani 1 d . . 1 . . .
H00V H 0.1616 0.5859 0.5015 0.031 Uiso 1 calc . . 1 GR . .
H00W H 0.1906 0.6486 0.4292 0.031 Uiso 1 calc . . 1 GR . .
H00X H 0.2068 0.4846 0.4674 0.031 Uiso 1 calc . . 1 GR . .
C00K C 0.08768(12) 0.6073(3) 0.35946(17) 0.0259(6) Uani 1 d . . 1 . . .
H00Y H 0.0579 0.5613 0.3205 0.039 Uiso 1 calc . . 1 GR . .
HA H 0.1053 0.6884 0.3328 0.039 Uiso 1 calc . . 1 GR . .
HB H 0.0723 0.6498 0.4050 0.039 Uiso 1 calc . . 1 GR . .
O1 O 0.0000 0.4298(15) 0.2500 0.031(4) Uani 0.259(13) d . . 2 S T P
H1 H -0.0168 0.3854 0.2853 0.047 Uiso 0.39(8) d . . 1 G . .


_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
S002 O7 1.4585(17) . ?
S002 O005 1.4642(18) . ?
S002 O006 1.4564(18) . ?
S002 C00F 1.773(2) . ?
O003 H00Z 0.8499 . ?
O003 H 0.8503 . ?
N007 C00C 1.520(3) . ?
N007 C00D 1.512(3) . ?
N007 C00E 1.503(3) . ?
N007 C00H 1.502(3) . ?
N008 C00A 1.515(3) . ?
N008 C00G 1.518(3) . ?
N008 C00J 1.500(3) . ?
N008 C00K 1.506(3) . ?
O00 H00 0.8500 . ?
C00A H00A 0.9700 . ?
C00A H00B 0.9700 . ?
C00A C00D 1.531(3) . ?
C00B H00C 0.9700 . ?
C00B H00D 0.9700 . ?
C00B C00F 1.530(3) . ?
C00B C00G 1.517(3) . ?
C00C H00E 0.9700 . ?
C00C H00F 0.9700 . ?
C00C C00I 1.509(3) . ?
C00D H00G 0.9700 . ?
C00D H00H 0.9700 . ?
C00E H00I 0.9600 . ?
C00E H00J 0.9600 . ?
C00E H00K 0.9600 . ?
C00F H00L 0.9700 . ?
C00F H00M 0.9700 . ?
C00G H00N 0.9700 . ?
C00G H00O 0.9700 . ?
C00H H00P 0.9600 . ?
C00H H00Q 0.9600 . ?
C00H H00R 0.9600 . ?
C00I H00S 0.9600 . ?
C00I H00T 0.9600 . ?
C00I H00U 0.9600 . ?
C00J H00V 0.9600 . ?
C00J H00W 0.9600 . ?
C00J H00X 0.9600 . ?
C00K H00Y 0.9600 . ?
C00K HA 0.9600 . ?
C00K HB 0.9600 . ?
O1 H1 0.8501 . ?

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
O7 S002 O005 112.24(11) . . ?
O7 S002 C00F 107.05(11) . . ?
O005 S002 C00F 105.08(11) . . ?
O006 S002 O7 112.60(10) . . ?
O006 S002 O005 112.86(11) . . ?
O006 S002 C00F 106.35(11) . . ?
H00Z O003 H 109.5 . . ?
C00D N007 C00C 112.68(18) . . ?
C00E N007 C00C 110.25(17) . . ?
C00E N007 C00D 106.77(17) . . ?
C00H N007 C00C 108.12(18) . . ?
C00H N007 C00D 110.81(17) . . ?
C00H N007 C00E 108.13(19) . . ?
C00A N008 C00G 108.94(17) . . ?
C00J N008 C00A 110.34(18) . . ?
C00J N008 C00G 112.27(18) . . ?
C00J N008 C00K 109.0(2) . . ?
C00K N008 C00A 106.78(18) . . ?
C00K N008 C00G 109.31(18) . . ?
N008 C00A H00A 109.3 . . ?
N008 C00A H00B 109.3 . . ?
N008 C00A C00D 111.72(18) . . ?
H00A C00A H00B 107.9 . . ?
C00D C00A H00A 109.3 . . ?
C00D C00A H00B 109.3 . . ?
H00C C00B H00D 108.6 . . ?
C00F C00B H00C 110.4 . . ?
C00F C00B H00D 110.4 . . ?
C00G C00B H00C 110.4 . . ?
C00G C00B H00D 110.4 . . ?
C00G C00B C00F 106.44(18) . . ?
N007 C00C H00E 108.7 . . ?
N007 C00C H00F 108.7 . . ?
H00E C00C H00F 107.6 . . ?
C00I C00C N007 114.38(19) . . ?
C00I C00C H00E 108.7 . . ?
C00I C00C H00F 108.7 . . ?
N007 C00D C00A 112.94(18) . . ?
N007 C00D H00G 109.0 . . ?
N007 C00D H00H 109.0 . . ?
C00A C00D H00G 109.0 . . ?
C00A C00D H00H 109.0 . . ?
H00G C00D H00H 107.8 . . ?
N007 C00E H00I 109.5 . . ?
N007 C00E H00J 109.5 . . ?
N007 C00E H00K 109.5 . . ?
H00I C00E H00J 109.5 . . ?
H00I C00E H00K 109.5 . . ?
H00J C00E H00K 109.5 . . ?
S002 C00F H00L 109.0 . . ?
S002 C00F H00M 109.0 . . ?
C00B C00F S002 112.84(16) . . ?
C00B C00F H00L 109.0 . . ?
C00B C00F H00M 109.0 . . ?
H00L C00F H00M 107.8 . . ?
N008 C00G H00N 108.2 . . ?
N008 C00G H00O 108.2 . . ?
C00B C00G N008 116.26(19) . . ?
C00B C00G H00N 108.2 . . ?
C00B C00G H00O 108.2 . . ?
H00N C00G H00O 107.4 . . ?
N007 C00H H00P 109.5 . . ?
N007 C00H H00Q 109.5 . . ?
N007 C00H H00R 109.5 . . ?
H00P C00H H00Q 109.5 . . ?
H00P C00H H00R 109.5 . . ?
H00Q C00H H00R 109.5 . . ?
C00C C00I H00S 109.5 . . ?
C00C C00I H00T 109.5 . . ?
C00C C00I H00U 109.5 . . ?
H00S C00I H00T 109.5 . . ?
H00S C00I H00U 109.5 . . ?
H00T C00I H00U 109.5 . . ?
N008 C00J H00V 109.5 . . ?
N008 C00J H00W 109.5 . . ?
N008 C00J H00X 109.5 . . ?
H00V C00J H00W 109.5 . . ?
H00V C00J H00X 109.5 . . ?
H00W C00J H00X 109.5 . . ?
N008 C00K H00Y 109.5 . . ?
N008 C00K HA 109.5 . . ?
N008 C00K HB 109.5 . . ?
H00Y C00K HA 109.5 . . ?
H00Y C00K HB 109.5 . . ?
HA C00K HB 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
O7 S002 C00F C00B -65.27(19) . . . . ?
O005 S002 C00F C00B 54.24(19) . . . . ?
O006 S002 C00F C00B 174.13(16) . . . . ?
N008 C00A C00D N007 -172.23(18) . . . . ?
C00A N008 C00G C00B -168.66(19) . . . . ?
C00C N007 C00D C00A -56.0(2) . . . . ?
C00D N007 C00C C00I -56.4(2) . . . . ?
C00E N007 C00C C00I 62.8(2) . . . . ?
C00E N007 C00D C00A -177.17(19) . . . . ?
C00F C00B C00G N008 -178.84(19) . . . . ?
C00G N008 C00A C00D 71.6(2) . . . . ?
C00G C00B C00F S002 -172.01(16) . . . . ?
C00H N007 C00C C00I -179.2(2) . . . . ?
C00H N007 C00D C00A 65.3(2) . . . . ?
C00J N008 C00A C00D -52.1(2) . . . . ?
C00J N008 C00G C00B -46.1(3) . . . . ?
C00K N008 C00A C00D -170.5(2) . . . . ?
C00K N008 C00G C00B 75.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
