# Electronic Supplementary Material (ESI) for ChemComm.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1818227'
_audit_update_record             
;
2018-01-19 deposited with the CCDC.
2018-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H40 Br2 N2 O8'
_chemical_formula_weight         716.46

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'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

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

_cell_length_a                   5.8799(2)
_cell_length_b                   29.0285(9)
_cell_length_c                   9.8495(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.082(3)
_cell_angle_gamma                90
_cell_volume                     1649.83(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    1832
_cell_measurement_theta_min      3.5020
_cell_measurement_theta_max      19.0040

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    2.506
_shelx_estimated_absorpt_T_min   0.788
_shelx_estimated_absorpt_T_max   0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.36411
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Empirical absorption correction'

_exptl_special_details           
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      200(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova Sapphire3'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13710
_diffrn_reflns_av_unetI/netI     0.1676
_diffrn_reflns_av_R_equivalents  0.0718
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.511
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.893
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.754
_diffrn_reflns_point_group_measured_fraction_full 0.888
_reflns_number_total             7265
_reflns_number_gt                3368
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.659
_reflns_Friedel_fraction_max     0.610
_reflns_Friedel_fraction_full    0.774

_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.
;

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0003P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 940 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7265
_refine_ls_number_parameters     431
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1728
_refine_ls_R_factor_gt           0.0673
_refine_ls_wR_factor_ref         0.0929
_refine_ls_wR_factor_gt          0.0663
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_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_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 0.3266(2) 0.09241(4) 0.96616(12) 0.0616(4) Uani 1 1 d . . . . .
O1 O 0.4954(11) -0.1064(2) 0.6384(7) 0.0352(18) Uani 1 1 d . . . . .
O2 O -0.2903(12) -0.1425(3) 0.4304(7) 0.048(2) Uani 1 1 d . . . . .
O3 O 0.2480(11) -0.1640(2) 0.8403(6) 0.0447(19) Uani 1 1 d . . . . .
O4 O 0.0810(10) -0.0960(2) 0.8765(6) 0.0313(15) Uani 1 1 d . . . . .
N1 N 0.0683(14) -0.1565(3) 0.5644(9) 0.032(2) Uani 1 1 d . . . . .
C1 C 0.3155(18) 0.0403(3) 0.8473(10) 0.040(3) Uani 1 1 d . . . . .
C2 C 0.5052(14) 0.0132(3) 0.8601(8) 0.033(2) Uani 1 1 d . . . . .
H2 H 0.6398 0.0210 0.9222 0.040 Uiso 1 1 calc R U . . .
C3 C 0.4976(14) -0.0268(3) 0.7790(9) 0.032(2) Uani 1 1 d . . . . .
H3 H 0.6286 -0.0452 0.7859 0.038 Uiso 1 1 calc R U . . .
C4 C 0.2948(15) -0.0388(3) 0.6887(9) 0.028(2) Uani 1 1 d . . . . .
C5 C 0.1049(16) -0.0094(3) 0.6777(10) 0.036(3) Uani 1 1 d . . . . .
H5 H -0.0305 -0.0167 0.6157 0.043 Uiso 1 1 calc R U . . .
C6 C 0.1109(16) 0.0304(3) 0.7558(9) 0.037(3) Uani 1 1 d . . . . .
H6 H -0.0173 0.0497 0.7473 0.044 Uiso 1 1 calc R U . . .
C7 C 0.2806(15) -0.0827(3) 0.6056(9) 0.030(2) Uani 1 1 d . . . . .
C8 C 0.2190(15) -0.0718(3) 0.4505(8) 0.040(3) Uani 1 1 d . . . . .
H8A H 0.0707 -0.0568 0.4300 0.048 Uiso 1 1 calc R U . . .
H8B H 0.2131 -0.0999 0.3984 0.048 Uiso 1 1 calc R U . . .
H8C H 0.3347 -0.0518 0.4259 0.048 Uiso 1 1 calc R U . . .
C9 C 0.0909(15) -0.1153(3) 0.6455(9) 0.028(2) Uani 1 1 d . . . . .
C10 C -0.1188(18) -0.1661(4) 0.4638(10) 0.043(3) Uani 1 1 d . . . . .
H10 H -0.1145 -0.1936 0.4158 0.051 Uiso 1 1 calc R U . . .
C11 C 0.1499(16) -0.1287(3) 0.7996(10) 0.031(2) Uani 1 1 d . . . . .
C12 C 0.1237(15) -0.0993(4) 1.0293(9) 0.028(2) Uani 1 1 d . . . . .
C13 C 0.0153(15) -0.0554(3) 1.0683(9) 0.040(3) Uani 1 1 d . . . . .
H13A H -0.1490 -0.0564 1.0345 0.048 Uiso 1 1 calc R U . . .
H13B H 0.0802 -0.0296 1.0281 0.048 Uiso 1 1 calc R U . . .
H13C H 0.0457 -0.0523 1.1672 0.048 Uiso 1 1 calc R U . . .
C14 C 0.3870(14) -0.0984(4) 1.0855(10) 0.043(3) Uani 1 1 d . . . . .
H14A H 0.4633 -0.1182 1.0304 0.052 Uiso 1 1 calc R U . . .
H14B H 0.4182 -0.1088 1.1797 0.052 Uiso 1 1 calc R U . . .
H14C H 0.4437 -0.0675 1.0813 0.052 Uiso 1 1 calc R U . . .
C15 C 0.007(2) -0.1416(4) 1.0723(13) 0.039(3) Uani 1 1 d . . . . .
Br2 Br 0.3504(2) -0.48451(4) 0.69236(13) 0.0665(4) Uani 1 1 d . . . . .
O5 O 0.0486(14) -0.2846(3) 0.3374(9) 0.057(3) Uani 1 1 d . . . . .
O6 O 0.7000(12) -0.2605(3) 0.1317(7) 0.066(3) Uani 1 1 d . . . . .
O7 O 0.3937(12) -0.2259(3) 0.5261(7) 0.058(2) Uani 1 1 d . . . . .
O8 O 0.6066(10) -0.2897(2) 0.5898(6) 0.0332(16) Uani 1 1 d . . . . .
N2 N 0.4361(19) -0.2401(4) 0.2593(10) 0.045(3) Uani 1 1 d . . . . .
C16 C 0.315(2) -0.4312(4) 0.5743(11) 0.048(3) Uani 1 1 d . . . . .
C17 C 0.1386(18) -0.4013(5) 0.5803(12) 0.050(3) Uani 1 1 d . . . . .
C18 C 0.1152(18) -0.3623(4) 0.4952(11) 0.042(3) Uani 1 1 d . . . . .
C19 C 0.2684(15) -0.3538(4) 0.4070(10) 0.034(3) Uani 1 1 d . . . . .
C20 C 0.4443(18) -0.3859(4) 0.4064(11) 0.043(3) Uani 1 1 d . . . . .
C21 C 0.472(2) -0.4247(4) 0.4888(12) 0.045(3) Uani 1 1 d . . . . .
C22 C 0.2455(17) -0.3117(4) 0.3131(10) 0.036(3) Uani 1 1 d . . . . .
C23 C 0.2079(16) -0.3257(4) 0.1624(10) 0.056(3) Uani 1 1 d . . . . .
H23A H 0.3142 -0.3092 0.1174 0.067 Uiso 1 1 calc R U . . .
H23B H 0.0518 -0.3185 0.1181 0.067 Uiso 1 1 calc R U . . .
H23C H 0.2337 -0.3582 0.1559 0.067 Uiso 1 1 calc R U . . .
C24 C 0.4597(15) -0.2797(3) 0.3541(9) 0.029(2) Uani 1 1 d . . . . .
C25 C 0.5601(19) -0.2344(4) 0.1606(11) 0.055(3) Uani 1 1 d . . . . .
H25 H 0.5349 -0.2075 0.1091 0.066 Uiso 1 1 calc R U . . .
C26 C 0.4831(16) -0.2611(4) 0.4991(9) 0.035(2) Uani 1 1 d . . . . .
C27 C 0.6360(16) -0.2818(3) 0.7414(9) 0.034(3) Uani 1 1 d . . . . .
C28 C 0.3983(14) -0.2834(4) 0.7816(10) 0.057(4) Uani 1 1 d . . . . .
H28A H 0.3452 -0.2526 0.7924 0.068 Uiso 1 1 calc R U . . .
H28B H 0.4093 -0.2999 0.8672 0.068 Uiso 1 1 calc R U . . .
H28C H 0.2908 -0.2989 0.7104 0.068 Uiso 1 1 calc R U . . .
C29 C 0.7832(16) -0.3220(3) 0.7997(10) 0.050(3) Uani 1 1 d . . . . .
H29A H 0.9282 -0.3110 0.8514 0.060 Uiso 1 1 calc R U . . .
H29B H 0.8111 -0.3413 0.7255 0.060 Uiso 1 1 calc R U . . .
H29C H 0.7044 -0.3393 0.8596 0.060 Uiso 1 1 calc R U . . .
C30 C 0.7589(16) -0.2362(3) 0.7801(10) 0.049(3) Uani 1 1 d . . . . .
H30A H 0.6601 -0.2113 0.7411 0.059 Uiso 1 1 calc R U . . .
H30B H 0.8998 -0.2354 0.7445 0.059 Uiso 1 1 calc R U . . .
H30C H 0.7943 -0.2332 0.8789 0.059 Uiso 1 1 calc R U . . .
H1O H 0.532(15) -0.121(3) 0.569(9) 0.05(3) Uiso 1 1 d . . . . .
H5O H -0.031(16) -0.288(4) 0.275(9) 0.04(4) Uiso 1 1 d . . . . .
H1N H 0.173(14) -0.178(3) 0.575(9) 0.05(3) Uiso 1 1 d . . . . .
H2N H 0.364(19) -0.223(4) 0.277(12) 0.07(5) Uiso 1 1 d . . . . .
H9 H -0.067(15) -0.099(3) 0.645(10) 0.07(3) Uiso 1 1 d . . . . .
H15A H 0.090(14) -0.172(3) 1.052(9) 0.05(3) Uiso 1 1 d . . . . .
H15B H -0.148(13) -0.145(3) 1.025(8) 0.02(2) Uiso 1 1 d . . . . .
H15C H 0.017(13) -0.142(3) 1.170(9) 0.04(3) Uiso 1 1 d . . . . .
H17 H 0.018(12) -0.403(3) 0.626(7) 0.03(3) Uiso 1 1 d . . . . .
H18 H -0.012(14) -0.343(3) 0.488(9) 0.05(3) Uiso 1 1 d . . . . .
H20 H 0.562(14) -0.381(3) 0.340(9) 0.05(3) Uiso 1 1 d . . . . .
H21 H 0.598(17) -0.442(4) 0.477(11) 0.09(5) Uiso 1 1 d . . . . .
H24 H 0.608(12) -0.299(3) 0.336(8) 0.02(2) 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
Br1 C1 1.906(9) . ?
O1 C7 1.419(10) . ?
O2 C10 1.211(11) . ?
O3 C11 1.206(10) . ?
O4 C11 1.325(10) . ?
O4 C12 1.481(10) . ?
N1 C10 1.360(10) . ?
N1 C9 1.430(11) . ?
C1 C2 1.351(12) . ?
C1 C6 1.388(11) . ?
C2 C3 1.405(12) . ?
C3 C4 1.388(11) . ?
C4 C5 1.393(12) . ?
C4 C7 1.510(12) . ?
C5 C6 1.384(12) . ?
C7 C8 1.534(11) . ?
C7 C9 1.569(12) . ?
C9 C11 1.540(12) . ?
C12 C15 1.505(13) . ?
C12 C13 1.505(12) . ?
C12 C14 1.541(11) . ?
Br2 C16 1.923(11) . ?
O5 C22 1.457(12) . ?
O6 C25 1.191(12) . ?
O7 C26 1.204(11) . ?
O8 C26 1.327(10) . ?
O8 C27 1.488(10) . ?
N2 C25 1.332(14) . ?
N2 C24 1.473(13) . ?
C16 C17 1.361(15) . ?
C16 C21 1.377(15) . ?
C17 C18 1.400(15) . ?
C18 C19 1.388(13) . ?
C19 C20 1.392(13) . ?
C19 C22 1.523(13) . ?
C20 C21 1.380(13) . ?
C22 C23 1.513(12) . ?
C22 C24 1.555(13) . ?
C24 C26 1.508(12) . ?
C27 C29 1.499(12) . ?
C27 C30 1.520(12) . ?
C27 C28 1.524(11) . ?

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
C11 O4 C12 121.7(7) . . ?
C10 N1 C9 123.6(8) . . ?
C2 C1 C6 122.4(9) . . ?
C2 C1 Br1 118.4(7) . . ?
C6 C1 Br1 119.1(7) . . ?
C1 C2 C3 119.5(8) . . ?
C4 C3 C2 120.1(9) . . ?
C3 C4 C5 118.2(9) . . ?
C3 C4 C7 120.7(8) . . ?
C5 C4 C7 121.0(8) . . ?
C6 C5 C4 122.3(9) . . ?
C5 C6 C1 117.4(9) . . ?
O1 C7 C4 109.3(7) . . ?
O1 C7 C8 110.9(8) . . ?
C4 C7 C8 110.0(8) . . ?
O1 C7 C9 107.2(7) . . ?
C4 C7 C9 110.0(8) . . ?
C8 C7 C9 109.4(7) . . ?
N1 C9 C11 108.6(8) . . ?
N1 C9 C7 111.0(8) . . ?
C11 C9 C7 111.2(7) . . ?
O2 C10 N1 126.7(10) . . ?
O3 C11 O4 126.6(9) . . ?
O3 C11 C9 123.0(9) . . ?
O4 C11 C9 110.4(8) . . ?
O4 C12 C15 109.9(8) . . ?
O4 C12 C13 102.0(7) . . ?
C15 C12 C13 112.4(8) . . ?
O4 C12 C14 109.0(7) . . ?
C15 C12 C14 113.1(8) . . ?
C13 C12 C14 109.8(8) . . ?
C26 O8 C27 121.5(7) . . ?
C25 N2 C24 124.1(11) . . ?
C17 C16 C21 123.0(12) . . ?
C17 C16 Br2 118.9(10) . . ?
C21 C16 Br2 118.1(9) . . ?
C16 C17 C18 118.5(11) . . ?
C19 C18 C17 121.1(11) . . ?
C18 C19 C20 117.2(10) . . ?
C18 C19 C22 122.0(10) . . ?
C20 C19 C22 120.8(9) . . ?
C21 C20 C19 123.1(11) . . ?
C16 C21 C20 117.1(12) . . ?
O5 C22 C23 109.6(8) . . ?
O5 C22 C19 108.3(8) . . ?
C23 C22 C19 111.1(9) . . ?
O5 C22 C24 105.3(8) . . ?
C23 C22 C24 111.9(8) . . ?
C19 C22 C24 110.4(8) . . ?
N2 C24 C26 107.5(9) . . ?
N2 C24 C22 109.3(8) . . ?
C26 C24 C22 112.5(8) . . ?
O6 C25 N2 126.7(12) . . ?
O7 C26 O8 126.1(9) . . ?
O7 C26 C24 123.3(9) . . ?
O8 C26 C24 110.6(9) . . ?
O8 C27 C29 102.3(8) . . ?
O8 C27 C30 110.1(8) . . ?
C29 C27 C30 111.7(7) . . ?
O8 C27 C28 108.7(7) . . ?
C29 C27 C28 111.5(8) . . ?
C30 C27 C28 112.2(9) . . ?

_refine_diff_density_max         0.404
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.083

_shelxl_version_number           2014-1

