# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_ACPBr
_audit_block_doi                 10.5517/ccdc.csd.cc20r9hl
_database_code_depnum_ccdc_archive 'CCDC 1869439'
_audit_update_record             
;
2018-09-24 deposited with the CCDC.
2018-12-12 downloaded from the CCDC.
;

_audit_creation_date             2017-08-28T14:30:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
(R)-3-(4-bromophenyl)isobenzofuran-1(3H)-one
;
_chemical_formula_moiety         'C14  H9  O2  Br1'
_chemical_formula_sum            'C14 H9 Br O2'
_chemical_formula_weight         289.12
_chemical_absolute_configuration rmad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.1663(3)
_cell_length_b                   11.1767(6)
_cell_length_c                   16.5802(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1142.69(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9456
_cell_measurement_theta_min      3.96
_cell_measurement_theta_max      79.09
_cell_measurement_wavelength     1.54178

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.243
_exptl_crystal_size_mid          0.292
_exptl_crystal_size_max          0.612
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    4.786
_exptl_absorpt_correction_T_min  0.4336
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; SADABS (version 2014/5; Bruker, 2014) was used to perform the multi-scan
 absorption correction.
;

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'Bruker D8 Venture Photon100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_number            43921
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.771
_diffrn_reflns_theta_max         79.536
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_number_total             2474
_reflns_number_gt                2456
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'APEX3 v2015.5-2 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    
'Diamond (version 3.2i; Crystal Impact GbR, Bonn, Germany)'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0243P)²+0.3589P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0124(6)
_refine_ls_number_reflns         2474
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0189
_refine_ls_R_factor_gt           0.0188
_refine_ls_wR_factor_ref         0.0492
_refine_ls_wR_factor_gt          0.0492
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 1006 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.008(4)
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.042

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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
O2 O -0.2195(3) 0.56794(14) 0.77359(9) 0.0291(3) Uani 1 d . .
C2 C -0.0224(3) 0.54965(19) 0.72720(12) 0.0249(4) Uani 1 d . .
C3 C -0.0643(3) 0.43616(19) 0.68155(13) 0.0259(4) Uani 1 d . .
O1 O -0.5365(3) 0.47562(18) 0.79371(12) 0.0426(4) Uani 1 d . .
C4 C -0.2675(4) 0.39393(18) 0.70248(12) 0.0273(4) Uani 1 d . .
C1 C -0.3627(3) 0.4771(2) 0.76052(14) 0.0292(4) Uani 1 d . .
C8 C 0.0632(5) 0.3742(2) 0.62654(15) 0.0377(5) Uani 1 d . .
H8 H 0.1996 0.4021 0.6118 0.045 Uiso 1 calc . .
C7 C -0.0197(6) 0.2695(2) 0.59447(17) 0.0489(7) Uani 1 d . .
H7 H 0.0634 0.2264 0.5578 0.059 Uiso 1 calc . .
C5 C -0.3515(4) 0.2886(2) 0.67011(15) 0.0384(6) Uani 1 d . .
H5 H -0.4882 0.2609 0.6847 0.046 Uiso 1 calc . .
C6 C -0.2249(6) 0.2268(2) 0.61568(16) 0.0493(7) Uani 1 d . .
H6 H -0.2763 0.1563 0.5929 0.059 Uiso 1 calc . .
Br Br 0.19199(5) 0.97562(2) 0.50428(2) 0.04946(13) Uani 1 d . .
C9 C 0.0255(3) 0.65745(18) 0.67491(12) 0.0231(4) Uani 1 d . .
C12 C 0.1240(4) 0.84707(19) 0.57464(13) 0.0300(5) Uani 1 d . .
C14 C 0.2305(3) 0.6669(2) 0.64026(13) 0.0296(4) Uani 1 d . .
H14 H 0.3348 0.609 0.6512 0.036 Uiso 1 calc . .
C11 C -0.0794(4) 0.8410(2) 0.60921(13) 0.0306(5) Uani 1 d . .
H11 H -0.1822 0.9 0.5991 0.037 Uiso 1 calc . .
C10 C -0.1276(3) 0.74506(18) 0.65950(13) 0.0263(4) Uani 1 d . .
H10 H -0.2642 0.7397 0.683 0.032 Uiso 1 calc . .
C13 C 0.2810(4) 0.7616(2) 0.58967(13) 0.0317(5) Uani 1 d . .
H13 H 0.4177 0.7675 0.5663 0.038 Uiso 1 calc . .
H2 H 0.091(4) 0.538(3) 0.7642(16) 0.028(6) Uiso 1 d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C1 1.363(3) . ?
O2 C2 1.453(3) . ?
C2 C3 1.500(3) . ?
C2 C9 1.513(3) . ?
C3 C4 1.384(3) . ?
C3 C8 1.389(3) . ?
O1 C1 1.205(3) . ?
C4 C5 1.394(3) . ?
C4 C1 1.461(3) . ?
C8 C7 1.383(4) . ?
C7 C6 1.397(5) . ?
C5 C6 1.379(4) . ?
Br C12 1.898(2) . ?
C9 C10 1.384(3) . ?
C9 C14 1.393(3) . ?
C12 C11 1.380(3) . ?
C12 C13 1.383(3) . ?
C14 C13 1.386(3) . ?
C11 C10 1.391(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
C1 O2 C2 110.69(16) . . ?
O2 C2 C3 104.02(17) . . ?
O2 C2 C9 110.76(17) . . ?
C3 C2 C9 114.70(17) . . ?
C4 C3 C8 120.5(2) . . ?
C4 C3 C2 108.53(19) . . ?
C8 C3 C2 131.0(2) . . ?
C3 C4 C5 121.9(2) . . ?
C3 C4 C1 108.18(19) . . ?
C5 C4 C1 129.9(2) . . ?
O1 C1 O2 120.9(2) . . ?
O1 C1 C4 130.5(2) . . ?
O2 C1 C4 108.56(17) . . ?
C7 C8 C3 117.7(3) . . ?
C8 C7 C6 121.8(3) . . ?
C6 C5 C4 117.7(2) . . ?
C5 C6 C7 120.4(3) . . ?
C10 C9 C14 119.30(19) . . ?
C10 C9 C2 122.41(18) . . ?
C14 C9 C2 118.29(19) . . ?
C11 C12 C13 121.8(2) . . ?
C11 C12 Br 119.55(18) . . ?
C13 C12 Br 118.62(17) . . ?
C13 C14 C9 120.8(2) . . ?
C12 C11 C10 118.8(2) . . ?
C9 C10 C11 120.7(2) . . ?
C12 C13 C14 118.6(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11 O1 0.93 2.62 3.235(3) 123.8 3_456
C2 H2 O1 0.94(3) 2.45(3) 3.298(3) 150(2) 1_655


# END of CIF
