# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_DR64
_database_code_depnum_ccdc_archive 'CCDC 2142979'
loop_
_audit_author_name
_audit_author_address
'Kevin Kenneth Klausmeyer'
;Baylor University
United States of America
;
_audit_update_record             
;
2022-01-18 deposited with the CCDC.	2023-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H11 Br O2'
_chemical_formula_weight         219.08

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'
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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   25.9184(7)
_cell_length_b                   5.4615(2)
_cell_length_c                   13.2419(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.6391(10)
_cell_angle_gamma                90
_cell_volume                     1717.15(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9861
_cell_measurement_theta_min      3.36
_cell_measurement_theta_max      28.28

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.284
_exptl_crystal_size_mid          0.267
_exptl_crystal_size_min          0.181
_exptl_absorpt_coefficient_mu    4.735
_shelx_estimated_absorpt_T_min   0.347
_shelx_estimated_absorpt_T_max   0.481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.212
_exptl_absorpt_correction_T_max  0.293
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15287
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.099
_diffrn_reflns_theta_max         28.278
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2123
_reflns_number_gt                2048
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0210P)²+1.9663P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2123
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0224
_refine_ls_R_factor_gt           0.0217
_refine_ls_wR_factor_ref         0.0537
_refine_ls_wR_factor_gt          0.0533
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_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 0.04589(2) 0.10737(3) 0.15635(2) 0.03351(7) Uani 1 1 d . . . . .
C1 C 0.15030(6) 0.1285(2) 0.13855(11) 0.0188(2) Uani 1 1 d . . . . .
H1 H 0.161320 0.256027 0.197645 0.023 Uiso 1 1 calc R U . . .
C2 C 0.19322(6) 0.1110(2) 0.08472(12) 0.0200(3) Uani 1 1 d . . . . .
H2 H 0.225110 0.228493 0.118986 0.024 Uiso 1 1 calc R U . . .
C3 C 0.17215(7) 0.1093(2) -0.04059(12) 0.0241(3) Uani 1 1 d . . . . .
H3A H 0.143724 -0.021854 -0.070845 0.029 Uiso 1 1 calc R U . . .
H3B H 0.204003 0.072109 -0.061322 0.029 Uiso 1 1 calc R U . . .
C4 C 0.14598(7) 0.3546(3) -0.09164(13) 0.0286(3) Uani 1 1 d . . . . .
H4A H 0.169298 0.488603 -0.045329 0.034 Uiso 1 1 calc R U . . .
H4B H 0.146975 0.368566 -0.165376 0.034 Uiso 1 1 calc R U . . .
C5 C 0.08534(7) 0.3889(3) -0.10362(13) 0.0307(3) Uani 1 1 d . . . . .
H5A H 0.062200 0.257686 -0.152451 0.037 Uiso 1 1 calc R U . . .
H5B H 0.071478 0.546580 -0.141724 0.037 Uiso 1 1 calc R U . . .
C6 C 0.07453(7) 0.3874(3) 0.00184(13) 0.0279(3) Uani 1 1 d . . . . .
H6A H 0.097087 0.519080 0.051265 0.033 Uiso 1 1 calc R U . . .
H6B H 0.034290 0.424256 -0.017370 0.033 Uiso 1 1 calc R U . . .
C7 C 0.08909(6) 0.1451(2) 0.06342(11) 0.0206(3) Uani 1 1 d . . . . .
H7 H 0.079303 0.007915 0.008888 0.025 Uiso 1 1 calc R U . . .
C8 C 0.20629(6) -0.1364(2) 0.14121(12) 0.0236(3) Uani 1 1 d . . . . .
O1 O 0.16686(4) -0.12063(18) 0.18480(9) 0.0255(2) Uani 1 1 d . . . . .
O2 O 0.23713(5) -0.3039(2) 0.15059(10) 0.0349(3) Uani 1 1 d . . . . .

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 0.02267(9) 0.05544(12) 0.02531(9) 0.00125(6) 0.01266(6) -0.00103(6)
C1 0.0188(6) 0.0180(6) 0.0190(6) 0.0001(4) 0.0068(5) -0.0002(4)
C2 0.0184(6) 0.0188(6) 0.0233(6) -0.0009(5) 0.0087(5) 0.0005(4)
C3 0.0286(7) 0.0235(6) 0.0242(7) 0.0002(5) 0.0147(6) 0.0036(5)
C4 0.0390(8) 0.0265(7) 0.0254(7) 0.0056(5) 0.0183(6) 0.0045(6)
C5 0.0365(8) 0.0306(8) 0.0253(7) 0.0087(5) 0.0126(6) 0.0115(6)
C6 0.0304(7) 0.0258(7) 0.0292(7) 0.0038(5) 0.0139(6) 0.0111(5)
C7 0.0184(6) 0.0256(6) 0.0189(6) -0.0007(5) 0.0086(5) 0.0013(5)
C8 0.0209(6) 0.0225(6) 0.0215(6) -0.0019(5) 0.0023(5) -0.0001(5)
O1 0.0227(5) 0.0242(5) 0.0262(5) 0.0076(4) 0.0062(4) 0.0001(4)
O2 0.0337(6) 0.0272(5) 0.0337(6) -0.0007(5) 0.0029(5) 0.0117(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 C7 1.9787(14) . ?
C1 O1 1.4831(15) . ?
C1 C7 1.4997(18) . ?
C1 C2 1.5462(19) . ?
C2 C8 1.5157(18) . ?
C2 C3 1.525(2) . ?
C3 C4 1.5307(19) . ?
C4 C5 1.527(2) . ?
C5 C6 1.531(2) . ?
C6 C7 1.5208(19) . ?
C8 O2 1.1880(18) . ?
C8 O1 1.3633(19) . ?

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
O1 C1 C7 112.54(10) . . ?
O1 C1 C2 89.49(9) . . ?
C7 C1 C2 117.60(11) . . ?
C8 C2 C3 116.32(11) . . ?
C8 C2 C1 83.53(10) . . ?
C3 C2 C1 119.47(11) . . ?
C2 C3 C4 112.17(11) . . ?
C5 C4 C3 114.13(13) . . ?
C4 C5 C6 117.52(13) . . ?
C7 C6 C5 113.38(12) . . ?
C1 C7 C6 112.16(12) . . ?
C1 C7 Br1 107.04(9) . . ?
C6 C7 Br1 110.08(9) . . ?
O2 C8 O1 126.28(14) . . ?
O2 C8 C2 138.24(15) . . ?
O1 C8 C2 95.47(10) . . ?
C8 O1 C1 91.44(10) . . ?

_refine_diff_density_max         0.476
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.062

_shelx_res_file                  
; 
TITL DR64 in C2/c 
    DR64.res 
    created by SHELXL-2018/3 at 09:40:04 on 18-Nov-2021 
CELL 0.71073  25.91840   5.46150  13.24190  90.0000 113.6391  90.0000 
ZERR    8.00   0.00070   0.00020   0.00040   0.0000   0.0010   0.0000 
LATT 7 
SYMM -X, Y, 0.5-Z 
SFAC C  H  O  Br 
UNIT 64  88  16  8 
L.S. 4 
BOND 
FMAP 2 
PLAN 5 
ACTA 
SIZE 0.181 0.267 0.284 
FREE C8   C1 
TEMP -123.150 
WGHT    0.021000    1.966300 
FVAR       0.11042 
MOLE 1 
BR1   4    0.045890    0.107374    0.156351    11.00000    0.02267    0.05544 = 
         0.02531    0.00125    0.01266   -0.00103 
C1    1    0.150300    0.128482    0.138546    11.00000    0.01878    0.01799 = 
         0.01904    0.00006    0.00682   -0.00016 
AFIX  13 
H1    2    0.161320    0.256027    0.197645    11.00000   -1.20000 
AFIX   0 
C2    1    0.193223    0.110993    0.084724    11.00000    0.01835    0.01875 = 
         0.02328   -0.00086    0.00875    0.00051 
AFIX  13 
H2    2    0.225110    0.228493    0.118986    11.00000   -1.20000 
AFIX   0 
C3    1    0.172151    0.109349   -0.040586    11.00000    0.02861    0.02348 = 
         0.02417    0.00023    0.01470    0.00363 
AFIX  23 
H3A   2    0.143724   -0.021854   -0.070845    11.00000   -1.20000 
H3B   2    0.204003    0.072109   -0.061322    11.00000   -1.20000 
AFIX   0 
C4    1    0.145977    0.354561   -0.091642    11.00000    0.03901    0.02651 = 
         0.02542    0.00558    0.01832    0.00447 
AFIX  23 
H4A   2    0.169298    0.488603   -0.045329    11.00000   -1.20000 
H4B   2    0.146975    0.368566   -0.165376    11.00000   -1.20000 
AFIX   0 
C5    1    0.085336    0.388876   -0.103620    11.00000    0.03646    0.03057 = 
         0.02533    0.00866    0.01263    0.01149 
AFIX  23 
H5A   2    0.062200    0.257686   -0.152451    11.00000   -1.20000 
H5B   2    0.071478    0.546580   -0.141724    11.00000   -1.20000 
AFIX   0 
C6    1    0.074530    0.387449    0.001843    11.00000    0.03044    0.02580 = 
         0.02919    0.00380    0.01391    0.01108 
AFIX  23 
H6A   2    0.097087    0.519080    0.051265    11.00000   -1.20000 
H6B   2    0.034290    0.424256   -0.017370    11.00000   -1.20000 
AFIX   0 
C7    1    0.089088    0.145068    0.063421    11.00000    0.01840    0.02558 = 
         0.01888   -0.00070    0.00857    0.00128 
AFIX  13 
H7    2    0.079303    0.007915    0.008888    11.00000   -1.20000 
AFIX   0 
C8    1    0.206293   -0.136443    0.141211    11.00000    0.02090    0.02246 = 
         0.02155   -0.00188    0.00233   -0.00008 
O1    3    0.166858   -0.120625    0.184803    11.00000    0.02266    0.02422 = 
         0.02616    0.00759    0.00624    0.00007 
O2    3    0.237130   -0.303939    0.150591    11.00000    0.03373    0.02718 = 
         0.03369   -0.00073    0.00291    0.01167 
HKLF 4 
  
  
  
  
REM  DR64 in C2/c 
REM wR2 = 0.053743, GooF = S = 1.06015, Restrained GooF = 1.06015 for all data 
REM R1 = 0.021737 for 2048 Fo > 4sig(Fo) and 0.022388 for all 2123 data 
REM 100 parameters refined using 0 restraints 
  
END 
  
WGHT      0.0209      1.9831 
  
REM Highest difference peak  0.476,  deepest hole -0.591,  1-sigma level  0.062 
Q1    1   0.0523 -0.0459  0.1508  11.00000  0.05    0.48 
Q2    1   0.1806  0.1105  0.0205  11.00000  0.05    0.36 
Q3    1   0.1209  0.1310  0.1002  11.00000  0.05    0.36 
Q4    1   0.1691  0.1363  0.1014  11.00000  0.05    0.34 
Q5    1   0.1997 -0.0193  0.1018  11.00000  0.05    0.26 
;
_shelx_res_checksum              69762
