# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
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#######################################################################

data_mx6831a
_database_code_depnum_ccdc_archive 'CCDC 1826704'
_audit_update_record             
;
2018-03-01 deposited with the CCDC.
2018-04-08 downloaded from the CCDC.
;
_audit_creation_date             2018-03-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H17 Br O4'
_chemical_formula_sum            'C16 H17 Br O4'
_chemical_formula_weight         353.20
_chemical_absolute_configuration ad
_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'
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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.573(4)
_cell_length_b                   7.311(2)
_cell_length_c                   11.350(4)
_cell_angle_alpha                90
_cell_angle_beta                 115.216(5)
_cell_angle_gamma                90
_cell_volume                     793.7(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2735
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4719
_cell_measurement_theta_min      1.9833
_shelx_estimated_absorpt_T_max   0.866
_shelx_estimated_absorpt_T_min   0.572
_exptl_absorpt_coefficient_mu    2.602
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73450
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.057
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9096
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         1.983
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_reflns_Friedel_coverage         0.842
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                3405
_reflns_number_total             3605
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 1332 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.016(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3605
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.076
_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)+(0.0270P)²+0.2297P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0793
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C5(H5), C8(H8)
2.d X=CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C13(H13A,H13B,H13C)
;
_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 0.68960(4) 0.27365(6) 0.88827(3) 0.04015(14) Uani 1 1 d . . . . .
O4 O 0.6728(2) 0.7566(5) 0.1581(2) 0.0295(6) Uani 1 1 d . . . . .
C10 C 0.7972(3) 0.7680(7) 0.2730(3) 0.0265(7) Uani 1 1 d . . . . .
H10 H 0.836699 0.894313 0.282595 0.032 Uiso 1 1 calc R . . . .
C14 C 0.6926(4) 0.7915(8) 0.0429(4) 0.0347(9) Uani 1 1 d . . . . .
H14A H 0.754808 0.697544 0.032940 0.042 Uiso 1 1 calc R . . . .
H14B H 0.736346 0.912926 0.048818 0.042 Uiso 1 1 calc R . . . .
C15 C 0.5522(4) 0.7861(9) -0.0714(4) 0.0402(9) Uani 1 1 d . . . . .
H15A H 0.563727 0.803477 -0.151948 0.060 Uiso 1 1 calc GR . . . .
H15B H 0.493193 0.883885 -0.063045 0.060 Uiso 1 1 calc GR . . . .
H15C H 0.507985 0.667422 -0.074099 0.060 Uiso 1 1 calc GR . . . .
C12 C 0.9279(4) 0.3244(6) 0.2237(4) 0.0285(10) Uani 1 1 d . . . . .
O1 O 0.8980(3) 0.6372(4) 0.2709(3) 0.0271(6) Uani 1 1 d . . . . .
O2 O 0.9102(4) 0.1612(4) 0.2217(4) 0.0404(9) Uani 1 1 d . . . . .
C2 C 0.8027(4) 0.3093(6) 0.7029(4) 0.0291(9) Uani 1 1 d . . . . .
H2 H 0.877758 0.237737 0.762442 0.035 Uiso 1 1 calc R . . . .
C7 C 0.6948(4) 0.5395(6) 0.3731(4) 0.0253(8) Uani 1 1 d . . . . .
H7 H 0.595442 0.549921 0.307116 0.030 Uiso 1 1 calc R . . . .
O3 O 1.0144(3) 0.4054(4) 0.1812(3) 0.0347(7) Uani 1 1 d . . . . .
C16 C 0.7921(5) 0.8432(6) 0.4814(4) 0.0345(10) Uani 1 1 d . . . . .
H16A H 0.837782 0.955054 0.481327 0.041 Uiso 1 1 calc R . . . .
H16B H 0.768572 0.815243 0.551357 0.041 Uiso 1 1 calc R . . . .
C3 C 0.8028(4) 0.3700(6) 0.5869(4) 0.0288(9) Uani 1 1 d . . . . .
H3 H 0.879853 0.341498 0.568036 0.035 Uiso 1 1 calc R . . . .
C1 C 0.6907(4) 0.3556(5) 0.7296(4) 0.0265(8) Uani 1 1 d . . . . .
C6 C 0.5805(4) 0.4582(6) 0.6446(4) 0.0294(9) Uani 1 1 d . . . . .
H6 H 0.504871 0.489023 0.665056 0.035 Uiso 1 1 calc R . . . .
C11 C 0.7613(4) 0.7270(5) 0.3845(4) 0.0269(9) Uani 1 1 d . . . . .
C13 C 1.0885(5) 0.2852(10) 0.1316(5) 0.0480(11) Uani 1 1 d . . . . .
H13A H 1.021353 0.220996 0.054489 0.072 Uiso 1 1 calc GR . . . .
H13B H 1.141992 0.195766 0.198697 0.072 Uiso 1 1 calc GR . . . .
H13C H 1.152409 0.357041 0.107892 0.072 Uiso 1 1 calc GR . . . .
C5 C 0.5813(4) 0.5161(6) 0.5283(4) 0.0293(9) Uani 1 1 d . . . . .
H5 H 0.505555 0.586693 0.468871 0.035 Uiso 1 1 calc R . . . .
C4 C 0.6925(4) 0.4716(5) 0.4982(4) 0.0242(8) Uani 1 1 d . . . . .
C9 C 0.8590(4) 0.4585(5) 0.2746(4) 0.0240(8) Uani 1 1 d . . . . .
C8 C 0.7667(4) 0.4072(5) 0.3192(4) 0.0266(8) Uani 1 1 d . . . . .
H8 H 0.744930 0.280876 0.317107 0.032 Uiso 1 1 calc R . . . .


_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 1.903(4) . ?
O4 C10 1.406(4) . ?
O4 C14 1.432(4) . ?
C10 O1 1.439(5) . ?
C10 C11 1.498(5) . ?
C14 C15 1.499(6) . ?
C12 O2 1.206(5) . ?
C12 O3 1.341(5) . ?
C12 C9 1.477(6) . ?
O1 C9 1.376(5) . ?
C2 C3 1.390(5) . ?
C2 C1 1.384(5) . ?
C7 C11 1.520(5) . ?
C7 C4 1.514(5) . ?
C7 C8 1.511(6) . ?
O3 C13 1.442(6) . ?
C16 C11 1.316(6) . ?
C3 C4 1.387(5) . ?
C1 C6 1.376(6) . ?
C6 C5 1.389(6) . ?
C5 C4 1.396(5) . ?
C9 C8 1.330(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
C10 O4 C14 113.2(3) . . ?
O4 C10 O1 110.6(3) . . ?
O4 C10 C11 107.3(3) . . ?
O1 C10 C11 109.7(3) . . ?
O4 C14 C15 108.0(3) . . ?
O2 C12 O3 123.7(4) . . ?
O2 C12 C9 124.4(4) . . ?
O3 C12 C9 111.9(3) . . ?
C9 O1 C10 113.4(3) . . ?
C1 C2 C3 118.3(4) . . ?
C4 C7 C11 114.0(3) . . ?
C8 C7 C11 108.5(3) . . ?
C8 C7 C4 112.4(3) . . ?
C12 O3 C13 116.0(4) . . ?
C4 C3 C2 121.3(4) . . ?
C2 C1 Br1 118.7(3) . . ?
C6 C1 Br1 119.4(3) . . ?
C6 C1 C2 121.9(4) . . ?
C1 C6 C5 119.1(4) . . ?
C10 C11 C7 112.5(4) . . ?
C16 C11 C10 121.0(4) . . ?
C16 C11 C7 126.4(4) . . ?
C6 C5 C4 120.6(4) . . ?
C3 C4 C7 120.8(3) . . ?
C3 C4 C5 118.8(4) . . ?
C5 C4 C7 120.4(3) . . ?
O1 C9 C12 114.5(3) . . ?
C8 C9 C12 121.7(4) . . ?
C8 C9 O1 123.8(4) . . ?
C9 C8 C7 123.4(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 C1 C6 C5 -179.4(3) . . . . ?
O4 C10 O1 C9 -66.6(4) . . . . ?
O4 C10 C11 C7 58.4(4) . . . . ?
O4 C10 C11 C16 -124.3(4) . . . . ?
C10 O4 C14 C15 -176.8(4) . . . . ?
C10 O1 C9 C12 158.0(3) . . . . ?
C10 O1 C9 C8 -21.7(5) . . . . ?
C14 O4 C10 O1 -59.8(5) . . . . ?
C14 O4 C10 C11 -179.5(4) . . . . ?
C12 C9 C8 C7 179.5(4) . . . . ?
O1 C10 C11 C7 -61.8(4) . . . . ?
O1 C10 C11 C16 115.5(4) . . . . ?
O1 C9 C8 C7 -0.8(6) . . . . ?
O2 C12 O3 C13 -0.2(7) . . . . ?
O2 C12 C9 O1 178.0(4) . . . . ?
O2 C12 C9 C8 -2.2(7) . . . . ?
C2 C3 C4 C7 179.0(4) . . . . ?
C2 C3 C4 C5 1.4(6) . . . . ?
C2 C1 C6 C5 0.4(6) . . . . ?
O3 C12 C9 O1 -1.1(5) . . . . ?
O3 C12 C9 C8 178.6(3) . . . . ?
C3 C2 C1 Br1 -179.9(3) . . . . ?
C3 C2 C1 C6 0.4(6) . . . . ?
C1 C2 C3 C4 -1.3(6) . . . . ?
C1 C6 C5 C4 -0.2(6) . . . . ?
C6 C5 C4 C7 -178.3(4) . . . . ?
C6 C5 C4 C3 -0.7(6) . . . . ?
C11 C10 O1 C9 51.7(4) . . . . ?
C11 C7 C4 C3 -89.8(5) . . . . ?
C11 C7 C4 C5 87.8(4) . . . . ?
C11 C7 C8 C9 -8.1(5) . . . . ?
C4 C7 C11 C10 164.4(3) . . . . ?
C4 C7 C11 C16 -12.7(6) . . . . ?
C4 C7 C8 C9 -135.1(4) . . . . ?
C9 C12 O3 C13 179.0(3) . . . . ?
C8 C7 C11 C10 38.3(4) . . . . ?
C8 C7 C11 C16 -138.9(4) . . . . ?
C8 C7 C4 C3 34.3(5) . . . . ?
C8 C7 C4 C5 -148.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
