# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_03363
_audit_block_doi                 10.5517/ccdc.csd.cc28jcsz
_database_code_depnum_ccdc_archive 'CCDC 2101111'
loop_
_audit_author_name
_audit_author_address
'Josefina Perles'
;Universidad Autonoma de Madrid
Spain
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2021-10-11 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            RR-626-F1_200K
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H13 Br O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         285.13
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   8.3815(2)
_cell_length_b                   7.13240(10)
_cell_length_c                   10.0251(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.8320(10)
_cell_angle_gamma                90
_cell_volume                     581.92(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9956
_cell_measurement_theta_min      2.5026
_cell_measurement_theta_max      26.1462
_cell_measurement_temperature    200.(2)

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.065
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288

_exptl_absorpt_coefficient_mu    3.521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.66
_exptl_absorpt_correction_T_max  0.80

_exptl_special_details           
;
;

_diffrn_ambient_temperature      200.(2)

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            22324
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12

_refine_special_details          
;
;

_reflns_number_total             2111
_reflns_number_gt                2051
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0195
_refine_ls_R_factor_gt           0.0183
_refine_ls_wR_factor_gt          0.0462
_refine_ls_wR_factor_ref         0.0547
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_restrained_S_all      1.183
_refine_ls_number_reflns         2111
_refine_ls_number_parameters     146
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0223P)²+0.1857P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.295
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 906 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.016(4)

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'

_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    'shelXle (C.B. Huebschle, rev 994)'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 -0.12221(4) 0.01906(8) 0.76130(4) 0.05028(14) Uani d . . . 1 . .
C C1 0.5415(5) 0.5982(5) 0.5775(4) 0.0352(8) Uani d . . . 1 . .
C C2 0.6765(4) 0.4976(8) 0.6758(4) 0.0452(9) Uani d . . . 1 . .
H H2A 0.776193 0.577061 0.693162 0.054 Uiso calc U . R 1 . .
H H2B 0.701529 0.380941 0.631267 0.054 Uiso calc U . R 1 . .
C C3 0.6415(5) 0.4464(6) 0.8137(4) 0.0440(9) Uani d . . . 1 . .
H H3A 0.573179 0.331645 0.804012 0.053 Uiso calc U . R 1 . .
H H3B 0.745843 0.421539 0.882118 0.053 Uiso calc U . R 1 . .
C C4 0.5517(5) 0.6081(6) 0.8614(4) 0.0389(8) Uani d . . . 1 . .
H H4A 0.621211 0.721886 0.871835 0.047 Uiso calc U . R 1 . .
H H4B 0.530989 0.577818 0.952154 0.047 Uiso calc U . R 1 . .
C C5 0.3895(4) 0.6466(5) 0.7595(3) 0.0314(7) Uani d . . . 1 . .
C C6 0.2634(4) 0.4928(6) 0.7566(3) 0.0290(7) Uani d . . . 1 . .
C C7 0.2164(5) 0.4458(5) 0.8772(4) 0.0396(9) Uani d . . . 1 . .
H H7 0.263725 0.511187 0.959742 0.048 Uiso calc U . R 1 . .
C C8 0.1021(5) 0.3060(6) 0.8787(4) 0.0405(9) Uani d . . . 1 . .
H H8 0.071568 0.275225 0.961414 0.049 Uiso calc U . R 1 . .
C C9 0.0334(4) 0.2123(5) 0.7586(4) 0.0347(8) Uani d . . . 1 . .
C C10 0.0741(5) 0.2565(5) 0.6380(4) 0.0384(8) Uani d . . . 1 . .
H H10 0.024327 0.191984 0.555614 0.046 Uiso calc U . R 1 . .
C C11 0.1887(5) 0.3964(5) 0.6375(3) 0.0344(8) Uani d . . . 1 . .
H H11 0.216902 0.42719 0.553785 0.041 Uiso calc U . R 1 . .
C C12 0.3177(5) 0.8357(5) 0.7864(4) 0.0416(9) Uani d . . . 1 . .
H H12A 0.220153 0.862584 0.711072 0.05 Uiso calc U . R 1 . .
H H12B 0.280777 0.828018 0.872937 0.05 Uiso calc U . R 1 . .
O O1 0.4132(3) 0.6681(4) 0.6196(2) 0.0338(5) Uani d . . . 1 . .
O O2 0.5421(4) 0.6257(5) 0.4588(3) 0.0554(8) Uani d . . . 1 . .
O O3 0.4306(4) 0.9853(4) 0.7963(3) 0.0520(8) Uani d . . . 1 . .
H H3O 0.435225 1.019407 0.717114 0.078 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C9 . 1.902(4) ?
C1 O2 . 1.208(5) ?
C1 O1 . 1.341(4) ?
C1 C2 . 1.495(6) ?
C2 C3 . 1.525(6) ?
C3 C4 . 1.516(5) ?
C4 C5 . 1.517(5) ?
C5 O1 . 1.471(4) ?
C5 C6 . 1.519(5) ?
C5 C12 . 1.527(5) ?
C6 C11 . 1.390(5) ?
C6 C7 . 1.400(5) ?
C7 C8 . 1.385(5) ?
C8 C9 . 1.377(5) ?
C9 C10 . 1.370(5) ?
C10 C11 . 1.386(5) ?
C12 O3 . 1.414(5) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 C1 O1 . . 116.3(4) ?
O2 C1 C2 . . 123.1(3) ?
O1 C1 C2 . . 120.6(3) ?
C1 C2 C3 . . 115.7(3) ?
C4 C3 C2 . . 108.7(3) ?
C3 C4 C5 . . 111.0(3) ?
O1 C5 C4 . . 110.9(3) ?
O1 C5 C6 . . 108.0(3) ?
C4 C5 C6 . . 112.9(3) ?
O1 C5 C12 . . 103.0(3) ?
C4 C5 C12 . . 111.6(3) ?
C6 C5 C12 . . 109.9(3) ?
C11 C6 C7 . . 117.5(3) ?
C11 C6 C5 . . 122.8(3) ?
C7 C6 C5 . . 119.7(3) ?
C8 C7 C6 . . 121.3(3) ?
C9 C8 C7 . . 119.0(3) ?
C10 C9 C8 . . 121.3(4) ?
C10 C9 Br1 . . 119.7(3) ?
C8 C9 Br1 . . 119.0(3) ?
C9 C10 C11 . . 119.2(3) ?
C10 C11 C6 . . 121.5(3) ?
O3 C12 C5 . . 113.2(3) ?
C1 O1 C5 . . 124.2(3) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 C1 C2 C3 . . . . -169.8(4) ?
O1 C1 C2 C3 . . . . 12.0(6) ?
C1 C2 C3 C4 . . . . -40.2(5) ?
C2 C3 C4 C5 . . . . 60.7(4) ?
C3 C4 C5 O1 . . . . -51.8(4) ?
C3 C4 C5 C6 . . . . 69.6(4) ?
C3 C4 C5 C12 . . . . -166.0(3) ?
O1 C5 C6 C11 . . . . -0.3(4) ?
C4 C5 C6 C11 . . . . -123.3(4) ?
C12 C5 C6 C11 . . . . 111.4(4) ?
O1 C5 C6 C7 . . . . -179.1(3) ?
C4 C5 C6 C7 . . . . 57.9(4) ?
C12 C5 C6 C7 . . . . -67.4(4) ?
C11 C6 C7 C8 . . . . 1.3(6) ?
C5 C6 C7 C8 . . . . -179.8(3) ?
C6 C7 C8 C9 . . . . -0.2(6) ?
C7 C8 C9 C10 . . . . -1.0(6) ?
C7 C8 C9 Br1 . . . . 179.5(3) ?
C8 C9 C10 C11 . . . . 1.1(6) ?
Br1 C9 C10 C11 . . . . -179.5(3) ?
C9 C10 C11 C6 . . . . 0.1(5) ?
C7 C6 C11 C10 . . . . -1.2(5) ?
C5 C6 C11 C10 . . . . 180.0(3) ?
O1 C5 C12 O3 . . . . -67.6(4) ?
C4 C5 C12 O3 . . . . 51.5(4) ?
C6 C5 C12 O3 . . . . 177.5(3) ?
O2 C1 O1 C5 . . . . 179.0(3) ?
C2 C1 O1 C5 . . . . -2.7(5) ?
C4 C5 O1 C1 . . . . 22.6(5) ?
C6 C5 O1 C1 . . . . -101.6(3) ?
C12 C5 O1 C1 . . . . 142.2(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C2 H2B Br1 1_655 0.99 3.10 3.813(5) 129.8 ?
C4 H4B O3 2_647 0.99 2.55 3.510(5) 163.0 ?
O3 H3O O2 2_656 0.84 1.97 2.806(4) 173.5 ?

