# 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_3i
_database_code_depnum_ccdc_archive 'CCDC 1818320'
_audit_update_record             
;
2018-01-20 deposited with the CCDC.
2018-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
Dimethyl [(2,2-diphenyl-3,4-dihydro-2H-chromen-4-yl)methyl]malonate
;
_chemical_name_common            ?
_chemical_melting_point_gt       404
_chemical_melting_point_lt       405
_chemical_formula_moiety         'C27 H26 O5'
_chemical_formula_sum            'C27 H26 O5'
_chemical_formula_weight         430.48

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   11.9068(6)
_cell_length_b                   10.5151(5)
_cell_length_c                   18.2449(8)
_cell_angle_alpha                90
_cell_angle_beta                 108.8820(10)
_cell_angle_gamma                90
_cell_volume                     2161.36(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9981
_cell_measurement_theta_min      2.360
_cell_measurement_theta_max      30.525

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   0.952
_exptl_transmission_factor_max   0.969
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23266
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.268
_diffrn_reflns_theta_max         29.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5745
_reflns_number_gt                5080
_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       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0518P)²+0.7973P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         5745
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1065
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
O1 O 0.78049(6) 0.44749(7) 0.51886(4) 0.02047(15) Uani 1 1 d . . . . .
O2 O 0.56919(9) -0.00851(9) 0.60842(5) 0.0385(2) Uani 1 1 d . . . . .
O3 O 0.55685(8) 0.10767(8) 0.70811(5) 0.02855(18) Uani 1 1 d . . . . .
O4 O 0.29943(8) 0.23581(11) 0.64039(6) 0.0472(3) Uani 1 1 d . . . . .
O5 O 0.25613(6) 0.09545(8) 0.54320(5) 0.02460(17) Uani 1 1 d . . . . .
C1 C 0.76306(8) 0.31090(9) 0.51852(5) 0.01639(18) Uani 1 1 d . . . . .
C2 C 0.63844(8) 0.28325(9) 0.52125(5) 0.01714(18) Uani 1 1 d . . . . .
H2A H 0.6241 0.1904 0.5176 0.021 Uiso 1 1 calc R U . . .
H2B H 0.5789 0.3241 0.4765 0.021 Uiso 1 1 calc R U . . .
C3 C 0.62458(8) 0.33365(9) 0.59657(5) 0.01609(18) Uani 1 1 d . . . . .
H3A H 0.6796 0.2846 0.6406 0.019 Uiso 1 1 calc R U . . .
C4 C 0.66278(8) 0.47224(9) 0.60591(5) 0.01727(18) Uani 1 1 d . . . . .
C5 C 0.73724(8) 0.51925(9) 0.56658(6) 0.01817(18) Uani 1 1 d . . . . .
C6 C 0.76939(9) 0.64765(10) 0.57082(6) 0.0225(2) Uani 1 1 d . . . . .
H6A H 0.8201 0.6775 0.5437 0.027 Uiso 1 1 calc R U . . .
C7 C 0.72737(10) 0.73123(10) 0.61453(6) 0.0255(2) Uani 1 1 d . . . . .
H7A H 0.7480 0.8187 0.6166 0.031 Uiso 1 1 calc R U . . .
C8 C 0.65493(10) 0.68686(10) 0.65526(6) 0.0256(2) Uani 1 1 d . . . . .
H8A H 0.6271 0.7434 0.6862 0.031 Uiso 1 1 calc R U . . .
C9 C 0.62342(9) 0.55919(10) 0.65050(6) 0.0216(2) Uani 1 1 d . . . . .
H9A H 0.5735 0.5298 0.6784 0.026 Uiso 1 1 calc R U . . .
C10 C 0.49802(8) 0.31678(9) 0.59922(6) 0.01890(19) Uani 1 1 d . . . . .
H10A H 0.4447 0.3754 0.5611 0.023 Uiso 1 1 calc R U . . .
H10B H 0.4967 0.3418 0.6513 0.023 Uiso 1 1 calc R U . . .
C11 C 0.44903(8) 0.18093(9) 0.58201(6) 0.01862(19) Uani 1 1 d . . . . .
H11A H 0.4385 0.1608 0.5266 0.022 Uiso 1 1 calc R U . . .
C12 C 0.53107(9) 0.08180(10) 0.63294(6) 0.02042(19) Uani 1 1 d . . . . .
C13 C 0.64033(12) 0.02178(12) 0.76072(7) 0.0337(3) Uani 1 1 d . . . . .
H13A H 0.6575 0.0520 0.8140 0.051 Uiso 1 1 calc R U . . .
H13B H 0.7140 0.0190 0.7477 0.051 Uiso 1 1 calc R U . . .
H13C H 0.6058 -0.0637 0.7559 0.051 Uiso 1 1 calc R U . . .
C14 C 0.32770(9) 0.17562(10) 0.59363(6) 0.0213(2) Uani 1 1 d . . . . .
C15 C 0.13679(10) 0.08451(13) 0.54716(8) 0.0319(3) Uani 1 1 d . . . . .
H15A H 0.0887 0.0318 0.5042 0.048 Uiso 1 1 calc R U . . .
H15B H 0.1012 0.1693 0.5436 0.048 Uiso 1 1 calc R U . . .
H15C H 0.1398 0.0451 0.5964 0.048 Uiso 1 1 calc R U . . .
C16 C 0.85910(8) 0.25160(9) 0.58788(5) 0.01682(18) Uani 1 1 d . . . . .
C17 C 0.85040(9) 0.12387(10) 0.60621(6) 0.0214(2) Uani 1 1 d . . . . .
H17A H 0.7842 0.0750 0.5765 0.026 Uiso 1 1 calc R U . . .
C18 C 0.93794(10) 0.06744(11) 0.66763(6) 0.0261(2) Uani 1 1 d . . . . .
H18A H 0.9307 -0.0194 0.6798 0.031 Uiso 1 1 calc R U . . .
C19 C 1.03568(10) 0.13731(12) 0.71115(6) 0.0273(2) Uani 1 1 d . . . . .
H19A H 1.0954 0.0987 0.7530 0.033 Uiso 1 1 calc R U . . .
C20 C 1.04534(9) 0.26383(12) 0.69304(6) 0.0270(2) Uani 1 1 d . . . . .
H20A H 1.1124 0.3119 0.7224 0.032 Uiso 1 1 calc R U . . .
C21 C 0.95750(9) 0.32141(10) 0.63197(6) 0.0221(2) Uani 1 1 d . . . . .
H21A H 0.9647 0.4085 0.6204 0.027 Uiso 1 1 calc R U . . .
C22 C 0.78174(9) 0.26828(10) 0.44323(6) 0.01942(19) Uani 1 1 d . . . . .
C23 C 0.88516(10) 0.30604(12) 0.42876(6) 0.0268(2) Uani 1 1 d . . . . .
H23A H 0.9418 0.3573 0.4655 0.032 Uiso 1 1 calc R U . . .
C24 C 0.90590(10) 0.26934(14) 0.36110(7) 0.0327(3) Uani 1 1 d . . . . .
H24A H 0.9762 0.2963 0.3517 0.039 Uiso 1 1 calc R U . . .
C25 C 0.82453(11) 0.19362(13) 0.30722(6) 0.0323(3) Uani 1 1 d . . . . .
H25A H 0.8391 0.1678 0.2612 0.039 Uiso 1 1 calc R U . . .
C26 C 0.72186(11) 0.15611(12) 0.32114(7) 0.0312(2) Uani 1 1 d . . . . .
H26A H 0.6657 0.1044 0.2843 0.037 Uiso 1 1 calc R U . . .
C27 C 0.70002(10) 0.19343(11) 0.38863(6) 0.0245(2) Uani 1 1 d . . . . .
H27A H 0.6289 0.1676 0.3973 0.029 Uiso 1 1 calc R U . . .


_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
O1 C5 1.3722(12) . ?
O1 C1 1.4509(11) . ?
O2 C12 1.1997(13) . ?
O3 C12 1.3330(13) . ?
O3 C13 1.4517(14) . ?
O4 C14 1.1949(14) . ?
O5 C14 1.3326(12) . ?
O5 C15 1.4506(12) . ?
C1 C22 1.5280(13) . ?
C1 C2 1.5286(13) . ?
C1 C16 1.5366(13) . ?
C2 C3 1.5309(13) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5196(13) . ?
C3 C10 1.5336(13) . ?
C3 H3A 1.0000 . ?
C4 C5 1.3989(14) . ?
C4 C9 1.4015(14) . ?
C5 C6 1.3987(13) . ?
C6 C7 1.3844(16) . ?
C6 H6A 0.9500 . ?
C7 C8 1.3888(17) . ?
C7 H7A 0.9500 . ?
C8 C9 1.3891(15) . ?
C8 H8A 0.9500 . ?
C9 H9A 0.9500 . ?
C10 C11 1.5365(14) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5220(14) . ?
C11 C14 1.5276(13) . ?
C11 H11A 1.0000 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C21 1.3960(13) . ?
C16 C17 1.3960(14) . ?
C17 C18 1.3923(15) . ?
C17 H17A 0.9500 . ?
C18 C19 1.3879(17) . ?
C18 H18A 0.9500 . ?
C19 C20 1.3845(18) . ?
C19 H19A 0.9500 . ?
C20 C21 1.3955(15) . ?
C20 H20A 0.9500 . ?
C21 H21A 0.9500 . ?
C22 C27 1.3897(14) . ?
C22 C23 1.3980(14) . ?
C23 C24 1.3895(15) . ?
C23 H23A 0.9500 . ?
C24 C25 1.3866(18) . ?
C24 H24A 0.9500 . ?
C25 C26 1.3840(18) . ?
C25 H25A 0.9500 . ?
C26 C27 1.3948(15) . ?
C26 H26A 0.9500 . ?
C27 H27A 0.9500 . ?

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
C5 O1 C1 117.68(7) . . ?
C12 O3 C13 115.70(9) . . ?
C14 O5 C15 115.70(8) . . ?
O1 C1 C22 103.42(7) . . ?
O1 C1 C2 109.10(8) . . ?
C22 C1 C2 113.49(8) . . ?
O1 C1 C16 109.32(7) . . ?
C22 C1 C16 109.59(8) . . ?
C2 C1 C16 111.56(8) . . ?
C1 C2 C3 110.56(7) . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 C2 108.50(8) . . ?
C4 C3 C10 111.65(8) . . ?
C2 C3 C10 112.38(8) . . ?
C4 C3 H3A 108.1 . . ?
C2 C3 H3A 108.1 . . ?
C10 C3 H3A 108.1 . . ?
C5 C4 C9 116.99(9) . . ?
C5 C4 C3 119.85(9) . . ?
C9 C4 C3 123.12(9) . . ?
O1 C5 C6 114.44(9) . . ?
O1 C5 C4 124.16(9) . . ?
C6 C5 C4 121.35(9) . . ?
C7 C6 C5 120.08(10) . . ?
C7 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
C6 C7 C8 119.85(10) . . ?
C6 C7 H7A 120.1 . . ?
C8 C7 H7A 120.1 . . ?
C7 C8 C9 119.55(10) . . ?
C7 C8 H8A 120.2 . . ?
C9 C8 H8A 120.2 . . ?
C8 C9 C4 122.17(10) . . ?
C8 C9 H9A 118.9 . . ?
C4 C9 H9A 118.9 . . ?
C3 C10 C11 114.39(8) . . ?
C3 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
C3 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C14 109.83(8) . . ?
C12 C11 C10 112.69(8) . . ?
C14 C11 C10 108.61(8) . . ?
C12 C11 H11A 108.5 . . ?
C14 C11 H11A 108.5 . . ?
C10 C11 H11A 108.5 . . ?
O2 C12 O3 123.79(10) . . ?
O2 C12 C11 124.06(10) . . ?
O3 C12 C11 112.15(9) . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O4 C14 O5 124.27(9) . . ?
O4 C14 C11 125.26(10) . . ?
O5 C14 C11 110.46(8) . . ?
O5 C15 H15A 109.5 . . ?
O5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 118.77(9) . . ?
C21 C16 C1 121.55(9) . . ?
C17 C16 C1 119.64(8) . . ?
C18 C17 C16 120.57(10) . . ?
C18 C17 H17A 119.7 . . ?
C16 C17 H17A 119.7 . . ?
C19 C18 C17 120.37(11) . . ?
C19 C18 H18A 119.8 . . ?
C17 C18 H18A 119.8 . . ?
C20 C19 C18 119.42(10) . . ?
C20 C19 H19A 120.3 . . ?
C18 C19 H19A 120.3 . . ?
C19 C20 C21 120.58(10) . . ?
C19 C20 H20A 119.7 . . ?
C21 C20 H20A 119.7 . . ?
C20 C21 C16 120.29(10) . . ?
C20 C21 H21A 119.9 . . ?
C16 C21 H21A 119.9 . . ?
C27 C22 C23 118.73(9) . . ?
C27 C22 C1 122.59(9) . . ?
C23 C22 C1 118.67(9) . . ?
C24 C23 C22 120.63(11) . . ?
C24 C23 H23A 119.7 . . ?
C22 C23 H23A 119.7 . . ?
C25 C24 C23 120.33(11) . . ?
C25 C24 H24A 119.8 . . ?
C23 C24 H24A 119.8 . . ?
C26 C25 C24 119.32(10) . . ?
C26 C25 H25A 120.3 . . ?
C24 C25 H25A 120.3 . . ?
C25 C26 C27 120.66(11) . . ?
C25 C26 H26A 119.7 . . ?
C27 C26 H26A 119.7 . . ?
C22 C27 C26 120.32(10) . . ?
C22 C27 H27A 119.8 . . ?
C26 C27 H27A 119.8 . . ?

_refine_diff_density_max         0.394
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.043


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_1e
_database_code_depnum_ccdc_archive 'CCDC 1818324'
_audit_update_record             
;
2018-01-20 deposited with the CCDC.
2018-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
Dimethyl 2-[5-bromo-2-(methoxymethoxy)phenyl]cyclopropane-1,1-dicarboxylate
;
_chemical_name_common            ?
_chemical_melting_point_gt       370
_chemical_melting_point_lt       371
_chemical_formula_moiety         'C14 H15 Br O6'
_chemical_formula_sum            'C14 H15 Br O6'
_chemical_formula_weight         359.17

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.0373(4)
_cell_length_b                   17.6384(9)
_cell_length_c                   10.4852(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.0790(10)
_cell_angle_gamma                90
_cell_volume                     1475.10(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6351
_cell_measurement_theta_min      2.272
_cell_measurement_theta_max      29.545

_exptl_crystal_description       NUGGET
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   0.334
_exptl_transmission_factor_max   0.440
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    2.811
_shelx_estimated_absorpt_T_min   0.334
_shelx_estimated_absorpt_T_max   0.440
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15155
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.272
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3571
_reflns_number_gt                3079
_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       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0364P)²+0.4347P] 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_number_reflns         3571
_refine_ls_number_parameters     197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0662
_refine_ls_wR_factor_gt          0.0633
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 0.78975(2) 0.63692(2) 0.53058(2) 0.02926(7) Uani 1 1 d . . . . .
O1 O 0.37245(14) 0.31081(7) 0.03727(11) 0.0256(3) Uani 1 1 d . . . . .
O2 O 0.57160(15) 0.34158(7) -0.08584(11) 0.0244(3) Uani 1 1 d . . . . .
O3 O 0.81612(16) 0.48537(7) 0.12075(12) 0.0307(3) Uani 1 1 d . . . . .
O4 O 0.84916(15) 0.35930(7) 0.10389(13) 0.0278(3) Uani 1 1 d . . . . .
O5 O 0.66603(16) 0.30564(7) 0.41900(12) 0.0235(3) Uani 1 1 d . . . . .
H1 H 0.725(2) 0.2817(12) 0.4641(18) 0.022(5) Uiso 1 1 d . . . . .
O6 O 0.84607(16) 0.34350(7) 0.63864(12) 0.0284(3) Uani 1 1 d . . . . .
C1 C 0.57812(18) 0.40281(9) 0.11290(14) 0.0166(3) Uani 1 1 d . . . . .
C2 C 0.50962(18) 0.41016(9) 0.24356(14) 0.0169(3) Uani 1 1 d . . . . .
H2A H 0.4224 0.3719 0.2590 0.020 Uiso 1 1 calc R U . . .
C3 C 0.4572(2) 0.46547(9) 0.13917(15) 0.0203(3) Uani 1 1 d . . . . .
H3A H 0.5021 0.5177 0.1494 0.024 Uiso 1 1 calc R U . . .
H3B H 0.3407 0.4621 0.0960 0.024 Uiso 1 1 calc R U . . .
C4 C 0.49767(19) 0.34496(9) 0.02107(15) 0.0179(3) Uani 1 1 d . . . . .
C5 C 0.4856(2) 0.29691(10) -0.19043(16) 0.0284(4) Uani 1 1 d . . . . .
H5A H 0.5490 0.2989 -0.2645 0.043 Uiso 1 1 calc R U . . .
H5B H 0.3730 0.3176 -0.2149 0.043 Uiso 1 1 calc R U . . .
H5C H 0.4770 0.2442 -0.1625 0.043 Uiso 1 1 calc R U . . .
C6 C 0.7589(2) 0.42232(9) 0.11137(14) 0.0204(3) Uani 1 1 d . . . . .
C7 C 1.0264(2) 0.36997(13) 0.09805(19) 0.0362(5) Uani 1 1 d . . . . .
H7A H 1.0767 0.3218 0.0763 0.054 Uiso 1 1 calc R U . . .
H7B H 1.0804 0.3876 0.1817 0.054 Uiso 1 1 calc R U . . .
H7C H 1.0423 0.4078 0.0322 0.054 Uiso 1 1 calc R U . . .
C8 C 0.62076(19) 0.43447(9) 0.36104(14) 0.0175(3) Uani 1 1 d . . . . .
C9 C 0.69273(19) 0.38040(9) 0.44692(15) 0.0186(3) Uani 1 1 d . . . . .
C10 C 0.7895(2) 0.40267(10) 0.56161(15) 0.0211(3) Uani 1 1 d . . . . .
C11 C 0.8215(2) 0.47866(10) 0.58837(15) 0.0230(3) Uani 1 1 d . . . . .
H11A H 0.8901 0.4939 0.6644 0.028 Uiso 1 1 calc R U . . .
C12 C 0.7499(2) 0.53190(9) 0.50015(16) 0.0211(3) Uani 1 1 d . . . . .
C13 C 0.6493(2) 0.51124(9) 0.38952(15) 0.0198(3) Uani 1 1 d . . . . .
H13A H 0.5994 0.5491 0.3327 0.024 Uiso 1 1 calc R U . . .
C14 C 0.9481(3) 0.36040(12) 0.75663(18) 0.0347(4) Uani 1 1 d . . . . .
H14A H 0.9835 0.3130 0.8008 0.052 Uiso 1 1 calc R U . . .
H14B H 0.8836 0.3908 0.8114 0.052 Uiso 1 1 calc R U . . .
H14C H 1.0472 0.3889 0.7386 0.052 Uiso 1 1 calc R U . . .


_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 C12 1.9001(17) . ?
O1 C4 1.2028(19) . ?
O2 C4 1.333(2) . ?
O2 C5 1.454(2) . ?
O3 C6 1.203(2) . ?
O4 C6 1.335(2) . ?
O4 C7 1.446(2) . ?
O5 C9 1.362(2) . ?
O5 H1 0.76(2) . ?
O6 C10 1.363(2) . ?
O6 C14 1.429(2) . ?
C1 C4 1.494(2) . ?
C1 C6 1.496(2) . ?
C1 C3 1.520(2) . ?
C1 C2 1.544(2) . ?
C2 C3 1.488(2) . ?
C2 C8 1.493(2) . ?
C2 H2A 1.0000 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.388(2) . ?
C8 C13 1.399(2) . ?
C9 C10 1.405(2) . ?
C10 C11 1.387(2) . ?
C11 C12 1.392(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.379(2) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
C4 O2 C5 116.03(13) . . ?
C6 O4 C7 116.06(14) . . ?
C9 O5 H1 109.6(16) . . ?
C10 O6 C14 117.85(14) . . ?
C4 C1 C6 119.61(13) . . ?
C4 C1 C3 112.20(13) . . ?
C6 C1 C3 118.61(13) . . ?
C4 C1 C2 117.13(13) . . ?
C6 C1 C2 116.33(12) . . ?
C3 C1 C2 58.12(10) . . ?
C3 C2 C8 120.35(14) . . ?
C3 C2 C1 60.13(10) . . ?
C8 C2 C1 120.93(12) . . ?
C3 C2 H2A 114.9 . . ?
C8 C2 H2A 114.9 . . ?
C1 C2 H2A 114.9 . . ?
C2 C3 C1 61.75(10) . . ?
C2 C3 H3A 117.6 . . ?
C1 C3 H3A 117.6 . . ?
C2 C3 H3B 117.6 . . ?
C1 C3 H3B 117.6 . . ?
H3A C3 H3B 114.7 . . ?
O1 C4 O2 124.32(14) . . ?
O1 C4 C1 123.65(14) . . ?
O2 C4 C1 111.72(13) . . ?
O2 C5 H5A 109.5 . . ?
O2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O3 C6 O4 124.75(15) . . ?
O3 C6 C1 125.02(15) . . ?
O4 C6 C1 110.16(13) . . ?
O4 C7 H7A 109.5 . . ?
O4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 118.82(14) . . ?
C9 C8 C2 119.82(14) . . ?
C13 C8 C2 121.31(14) . . ?
O5 C9 C8 118.93(14) . . ?
O5 C9 C10 120.69(15) . . ?
C8 C9 C10 120.37(15) . . ?
O6 C10 C11 125.46(15) . . ?
O6 C10 C9 113.71(15) . . ?
C11 C10 C9 120.83(15) . . ?
C10 C11 C12 117.79(15) . . ?
C10 C11 H11A 121.1 . . ?
C12 C11 H11A 121.1 . . ?
C13 C12 C11 122.17(15) . . ?
C13 C12 Br1 117.92(13) . . ?
C11 C12 Br1 119.91(13) . . ?
C12 C13 C8 119.94(15) . . ?
C12 C13 H13A 120.0 . . ?
C8 C13 H13A 120.0 . . ?
O6 C14 H14A 109.5 . . ?
O6 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O6 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
O5 H1 O1 0.76(2) 2.10(2) 2.8288(17) 160(2) 4_666

_refine_diff_density_max         0.420
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.068


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_1c
_database_code_depnum_ccdc_archive 'CCDC 1818632'
_audit_update_record             
;
2018-01-22 deposited with the CCDC.
2018-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
Dimethyl 2-(5-bromo-2-hydroxyphenyl)cyclopropane-1,1-dicarboxylate
;
_chemical_name_common            ?
_chemical_melting_point_gt       385
_chemical_melting_point_lt       386
_chemical_formula_moiety         'C13 H13 Br O5'
_chemical_formula_sum            'C13 H13 Br O5'
_chemical_formula_weight         329.14

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   8.4387(11)
_cell_length_b                   8.5555(11)
_cell_length_c                   9.4816(12)
_cell_angle_alpha                97.917(2)
_cell_angle_beta                 100.060(2)
_cell_angle_gamma                92.556(2)
_cell_volume                     665.94(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4196
_cell_measurement_theta_min      2.206
_cell_measurement_theta_max      30.352

_exptl_crystal_description       NUGGET
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   0.280
_exptl_transmission_factor_max   0.410
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    3.099
_shelx_estimated_absorpt_T_min   0.280
_shelx_estimated_absorpt_T_max   0.410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7912
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.206
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3855
_reflns_number_gt                3412
_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       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0302P)²+0.3079P] 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_number_reflns         3855
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0273
_refine_ls_wR_factor_ref         0.0670
_refine_ls_wR_factor_gt          0.0643
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 0.23548(2) 0.11622(2) 0.34055(2) 0.03014(6) Uani 1 1 d . . . . .
O1 O 0.17887(18) 0.85146(15) 1.01366(13) 0.0329(3) Uani 1 1 d . . . . .
O2 O 0.28567(16) 0.97312(14) 0.85459(13) 0.0276(3) Uani 1 1 d . . . . .
O3 O 0.18717(14) 0.51190(14) 0.93989(12) 0.0226(2) Uani 1 1 d . . . . .
O4 O 0.01918(13) 0.47606(13) 0.72624(12) 0.0205(2) Uani 1 1 d . . . . .
O5 O 0.56072(16) 0.56930(15) 0.86539(13) 0.0268(3) Uani 1 1 d . . . . .
H1 H 0.622(3) 0.529(3) 0.915(3) 0.047(7) Uiso 1 1 d . . . . .
C1 C 0.19486(18) 0.70703(17) 0.78266(15) 0.0168(3) Uani 1 1 d . . . . .
C2 C 0.32220(18) 0.68126(18) 0.68239(15) 0.0172(3) Uani 1 1 d . . . . .
H2A H 0.4119 0.7659 0.6994 0.021 Uiso 1 1 calc R U . . .
C3 C 0.15954(19) 0.72999(19) 0.62387(16) 0.0193(3) Uani 1 1 d . . . . .
H3A H 0.0845 0.6502 0.5559 0.023 Uiso 1 1 calc R U . . .
H3B H 0.1518 0.8396 0.6022 0.023 Uiso 1 1 calc R U . . .
C4 C 0.21746(19) 0.84808(18) 0.89704(16) 0.0192(3) Uani 1 1 d . . . . .
C5 C 0.3112(3) 1.1155(2) 0.9604(2) 0.0342(4) Uani 1 1 d . . . . .
H5A H 0.3582 1.2018 0.9193 0.051 Uiso 1 1 calc R U . . .
H5B H 0.3849 1.0964 1.0473 0.051 Uiso 1 1 calc R U . . .
H5C H 0.2078 1.1447 0.9861 0.051 Uiso 1 1 calc R U . . .
C6 C 0.13403(17) 0.55796(18) 0.82724(15) 0.0169(3) Uani 1 1 d . . . . .
C7 C -0.0275(2) 0.3194(2) 0.75443(19) 0.0292(4) Uani 1 1 d . . . . .
H7A H -0.1252 0.2763 0.6855 0.044 Uiso 1 1 calc R U . . .
H7B H -0.0488 0.3264 0.8534 0.044 Uiso 1 1 calc R U . . .
H7C H 0.0599 0.2497 0.7434 0.044 Uiso 1 1 calc R U . . .
C8 C 0.37005(17) 0.51637(18) 0.64922(15) 0.0169(3) Uani 1 1 d . . . . .
C9 C 0.49142(18) 0.46318(19) 0.74884(16) 0.0193(3) Uani 1 1 d . . . . .
C10 C 0.5337(2) 0.3073(2) 0.72789(17) 0.0237(3) Uani 1 1 d . . . . .
H10A H 0.6160 0.2720 0.7957 0.028 Uiso 1 1 calc R U . . .
C11 C 0.4554(2) 0.2036(2) 0.60763(18) 0.0248(3) Uani 1 1 d . . . . .
H11A H 0.4819 0.0965 0.5940 0.030 Uiso 1 1 calc R U . . .
C12 C 0.33857(19) 0.25744(19) 0.50790(16) 0.0209(3) Uani 1 1 d . . . . .
C13 C 0.29548(18) 0.41247(18) 0.52704(16) 0.0185(3) Uani 1 1 d . . . . .
H13A H 0.2155 0.4476 0.4571 0.022 Uiso 1 1 calc R U . . .


_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 C12 1.9053(16) . ?
O1 C4 1.2030(19) . ?
O2 C4 1.3351(19) . ?
O2 C5 1.450(2) . ?
O3 C6 1.2089(18) . ?
O4 C6 1.3332(18) . ?
O4 C7 1.454(2) . ?
O5 C9 1.3558(19) . ?
O5 H1 0.76(3) . ?
C1 C4 1.488(2) . ?
C1 C6 1.495(2) . ?
C1 C3 1.5245(19) . ?
C1 C2 1.558(2) . ?
C2 C3 1.488(2) . ?
C2 C8 1.492(2) . ?
C2 H2A 1.0000 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C13 1.393(2) . ?
C8 C9 1.404(2) . ?
C9 C10 1.392(2) . ?
C10 C11 1.389(2) . ?
C10 H10A 0.9500 . ?
C11 C12 1.383(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.387(2) . ?
C13 H13A 0.9500 . ?

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
C4 O2 C5 114.93(13) . . ?
C6 O4 C7 115.15(12) . . ?
C9 O5 H1 109(2) . . ?
C4 C1 C6 114.90(12) . . ?
C4 C1 C3 119.31(13) . . ?
C6 C1 C3 119.88(12) . . ?
C4 C1 C2 119.14(13) . . ?
C6 C1 C2 113.66(12) . . ?
C3 C1 C2 57.72(9) . . ?
C3 C2 C8 122.35(13) . . ?
C3 C2 C1 60.01(9) . . ?
C8 C2 C1 116.79(12) . . ?
C3 C2 H2A 115.4 . . ?
C8 C2 H2A 115.4 . . ?
C1 C2 H2A 115.4 . . ?
C2 C3 C1 62.27(9) . . ?
C2 C3 H3A 117.5 . . ?
C1 C3 H3A 117.5 . . ?
C2 C3 H3B 117.5 . . ?
C1 C3 H3B 117.5 . . ?
H3A C3 H3B 114.6 . . ?
O1 C4 O2 123.32(14) . . ?
O1 C4 C1 124.96(14) . . ?
O2 C4 C1 111.72(13) . . ?
O2 C5 H5A 109.5 . . ?
O2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O3 C6 O4 122.98(14) . . ?
O3 C6 C1 124.11(13) . . ?
O4 C6 C1 112.83(12) . . ?
O4 C7 H7A 109.5 . . ?
O4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 119.15(14) . . ?
C13 C8 C2 122.76(13) . . ?
C9 C8 C2 118.05(13) . . ?
O5 C9 C10 122.77(14) . . ?
O5 C9 C8 116.76(14) . . ?
C10 C9 C8 120.46(14) . . ?
C11 C10 C9 119.86(14) . . ?
C11 C10 H10A 120.1 . . ?
C9 C10 H10A 120.1 . . ?
C12 C11 C10 119.51(15) . . ?
C12 C11 H11A 120.2 . . ?
C10 C11 H11A 120.2 . . ?
C11 C12 C13 121.28(15) . . ?
C11 C12 Br1 119.37(12) . . ?
C13 C12 Br1 119.35(11) . . ?
C12 C13 C8 119.71(14) . . ?
C12 C13 H13A 120.1 . . ?
C8 C13 H13A 120.1 . . ?

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
O5 H1 O3 0.76(3) 2.01(3) 2.7442(16) 163(3) 2_667

_refine_diff_density_max         0.852
_refine_diff_density_min         -0.819
_refine_diff_density_rms         0.065


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_S2b
_database_code_depnum_ccdc_archive 'CCDC 1818322'
_audit_update_record             
;
2018-01-20 deposited with the CCDC.
2018-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
Dimethyl 2-[5-chloro-2-(methoxymethoxy)phenyl]cyclopropane-1,1-dicarboxylate
;
_chemical_name_common            ?
_chemical_melting_point_gt       350
_chemical_melting_point_lt       351
_chemical_formula_moiety         'C15 H17 Cl O6'
_chemical_formula_sum            'C15 H17 Cl O6'
_chemical_formula_weight         328.73

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   8.835(2)
_cell_length_b                   6.916(2)
_cell_length_c                   24.341(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.48(3)
_cell_angle_gamma                90
_cell_volume                     1487.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      12.38
_cell_measurement_theta_max      12.89

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   0.871
_exptl_transmission_factor_max   0.945
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.284
_shelx_estimated_absorpt_T_min   0.871
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SHELXTL (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        0
_diffrn_reflns_number            2916
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -2
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.305
_diffrn_reflns_theta_max         25.977
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2916
_reflns_number_gt                2382
_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       'Enraf-Nonius CAD4 Software package'
_computing_cell_refinement       'Enraf-Nonius CAD4 Software package'
_computing_data_reduction        'XCAD4PC (Harms, 1997)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0485P)²+0.6233P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         2916
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0821
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.002
_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
Cl1 Cl 0.15341(5) 0.40120(6) 0.61173(2) 0.03035(13) Uani 1 1 d . . . . .
O1 O 0.39896(13) 0.57316(16) 0.42474(4) 0.0278(3) Uani 1 1 d . . . . .
O2 O 0.33987(12) 0.47196(16) 0.33972(4) 0.0248(3) Uani 1 1 d . . . . .
O3 O 0.61262(13) 0.27488(18) 0.30919(5) 0.0312(3) Uani 1 1 d . . . . .
O4 O 0.55255(13) -0.01395(17) 0.34441(4) 0.0264(3) Uani 1 1 d . . . . .
O5 O 0.13353(11) 0.08393(16) 0.38817(4) 0.0233(2) Uani 1 1 d . . . . .
O6 O 0.02944(12) -0.00618(16) 0.30661(4) 0.0254(3) Uani 1 1 d . . . . .
C1 C 0.48129(16) 0.2609(2) 0.39459(6) 0.0186(3) Uani 1 1 d . . . . .
C2 C 0.55758(16) 0.2160(2) 0.44951(6) 0.0211(3) Uani 1 1 d . . . . .
H2A H 0.6486 0.1325 0.4491 0.025 Uiso 1 1 calc R U . . .
H2B H 0.5597 0.3196 0.4776 0.025 Uiso 1 1 calc R U . . .
C3 C 0.40920(15) 0.1242(2) 0.43688(6) 0.0183(3) Uani 1 1 d . . . . .
H3A H 0.4146 -0.0162 0.4273 0.022 Uiso 1 1 calc R U . . .
C4 C 0.40638(15) 0.4539(2) 0.38878(6) 0.0186(3) Uani 1 1 d . . . . .
C5 C 0.25398(18) 0.6483(2) 0.33070(7) 0.0278(4) Uani 1 1 d . . . . .
H5A H 0.2299 0.6614 0.2915 0.042 Uiso 1 1 calc R U . . .
H5B H 0.3141 0.7597 0.3428 0.042 Uiso 1 1 calc R U . . .
H5C H 0.1599 0.6428 0.3517 0.042 Uiso 1 1 calc R U . . .
C6 C 0.55403(15) 0.1795(2) 0.34440(6) 0.0202(3) Uani 1 1 d . . . . .
C7 C 0.62038(19) -0.1060(3) 0.29721(7) 0.0299(4) Uani 1 1 d . . . . .
H7A H 0.6152 -0.2467 0.3014 0.045 Uiso 1 1 calc R U . . .
H7B H 0.7265 -0.0660 0.2944 0.045 Uiso 1 1 calc R U . . .
H7C H 0.5654 -0.0675 0.2638 0.045 Uiso 1 1 calc R U . . .
C8 C 0.26874(16) 0.1833(2) 0.46617(6) 0.0175(3) Uani 1 1 d . . . . .
C9 C 0.12839(16) 0.1610(2) 0.43984(6) 0.0183(3) Uani 1 1 d . . . . .
C10 C -0.00407(17) 0.2131(2) 0.46658(6) 0.0216(3) Uani 1 1 d . . . . .
H10A H -0.0989 0.1997 0.4483 0.026 Uiso 1 1 calc R U . . .
C11 C 0.00177(17) 0.2845(2) 0.51972(6) 0.0228(3) Uani 1 1 d . . . . .
H11A H -0.0886 0.3185 0.5383 0.027 Uiso 1 1 calc R U . . .
C12 C 0.14065(17) 0.3056(2) 0.54530(6) 0.0212(3) Uani 1 1 d . . . . .
C13 C 0.27393(16) 0.2559(2) 0.51917(6) 0.0199(3) Uani 1 1 d . . . . .
H13A H 0.3684 0.2715 0.5375 0.024 Uiso 1 1 calc R U . . .
C14 C -0.00193(17) 0.0840(2) 0.35561(6) 0.0239(3) Uani 1 1 d . . . . .
H14A H -0.0834 0.0140 0.3750 0.029 Uiso 1 1 calc R U . . .
H14B H -0.0360 0.2183 0.3488 0.029 Uiso 1 1 calc R U . . .
C15 C 0.1258(2) 0.1032(3) 0.27150(7) 0.0362(4) Uani 1 1 d . . . . .
H15A H 0.1485 0.0275 0.2385 0.054 Uiso 1 1 calc R U . . .
H15B H 0.2203 0.1338 0.2910 0.054 Uiso 1 1 calc R U . . .
H15C H 0.0748 0.2235 0.2608 0.054 Uiso 1 1 calc R U . . .


_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
Cl1 C12 1.7497(16) . ?
O1 C4 1.2046(18) . ?
O2 C4 1.3325(18) . ?
O2 C5 1.4520(19) . ?
O3 C6 1.2021(19) . ?
O4 C6 1.338(2) . ?
O4 C7 1.4478(19) . ?
O5 C9 1.3671(18) . ?
O5 C14 1.4298(18) . ?
O6 C14 1.3761(19) . ?
O6 C15 1.428(2) . ?
C1 C6 1.495(2) . ?
C1 C4 1.496(2) . ?
C1 C2 1.524(2) . ?
C1 C3 1.540(2) . ?
C2 C3 1.487(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C8 1.4934(19) . ?
C3 H3A 1.0000 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C13 1.385(2) . ?
C8 C9 1.400(2) . ?
C9 C10 1.391(2) . ?
C10 C11 1.385(2) . ?
C10 H10A 0.9500 . ?
C11 C12 1.379(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.386(2) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C4 O2 C5 116.10(12) . . ?
C6 O4 C7 115.81(13) . . ?
C9 O5 C14 118.41(11) . . ?
C14 O6 C15 113.83(13) . . ?
C6 C1 C4 116.83(12) . . ?
C6 C1 C2 116.74(12) . . ?
C4 C1 C2 117.19(13) . . ?
C6 C1 C3 119.87(13) . . ?
C4 C1 C3 115.23(12) . . ?
C2 C1 C3 58.05(9) . . ?
C3 C2 C1 61.51(9) . . ?
C3 C2 H2A 117.6 . . ?
C1 C2 H2A 117.6 . . ?
C3 C2 H2B 117.6 . . ?
C1 C2 H2B 117.6 . . ?
H2A C2 H2B 114.7 . . ?
C2 C3 C8 121.28(13) . . ?
C2 C3 C1 60.45(9) . . ?
C8 C3 C1 120.06(12) . . ?
C2 C3 H3A 114.8 . . ?
C8 C3 H3A 114.8 . . ?
C1 C3 H3A 114.8 . . ?
O1 C4 O2 124.12(14) . . ?
O1 C4 C1 124.66(13) . . ?
O2 C4 C1 111.07(12) . . ?
O2 C5 H5A 109.5 . . ?
O2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O3 C6 O4 123.57(14) . . ?
O3 C6 C1 124.52(15) . . ?
O4 C6 C1 111.84(13) . . ?
O4 C7 H7A 109.5 . . ?
O4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 119.27(13) . . ?
C13 C8 C3 121.52(13) . . ?
C9 C8 C3 119.20(13) . . ?
O5 C9 C10 124.47(14) . . ?
O5 C9 C8 115.35(12) . . ?
C10 C9 C8 120.18(14) . . ?
C11 C10 C9 120.29(14) . . ?
C11 C10 H10A 119.9 . . ?
C9 C10 H10A 119.9 . . ?
C12 C11 C10 119.03(14) . . ?
C12 C11 H11A 120.5 . . ?
C10 C11 H11A 120.5 . . ?
C11 C12 C13 121.51(14) . . ?
C11 C12 Cl1 120.48(12) . . ?
C13 C12 Cl1 117.99(12) . . ?
C8 C13 C12 119.72(14) . . ?
C8 C13 H13A 120.1 . . ?
C12 C13 H13A 120.1 . . ?
O6 C14 O5 107.86(12) . . ?
O6 C14 H14A 110.1 . . ?
O5 C14 H14A 110.1 . . ?
O6 C14 H14B 110.1 . . ?
O5 C14 H14B 110.1 . . ?
H14A C14 H14B 108.4 . . ?
O6 C15 H15A 109.5 . . ?
O6 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O6 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_refine_diff_density_max         0.396
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.048


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 1818323'
_audit_update_record             
;
2018-01-20 deposited with the CCDC.
2018-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
Dimethyl 2-(5-chloro-2-hydroxyphenyl)cyclopropane-1,1-dicarboxylate
;
_chemical_name_common            ?
_chemical_melting_point_gt       373
_chemical_melting_point_lt       374
_chemical_formula_moiety         'C13 H13 Cl O5'
_chemical_formula_sum            'C13 H13 Cl O5'
_chemical_formula_weight         284.68

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   9.594(2)
_cell_length_b                   8.102(2)
_cell_length_c                   17.944(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.50(2)
_cell_angle_gamma                90
_cell_volume                     1350.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      13
_cell_measurement_theta_max      14

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   0.350
_exptl_transmission_factor_max   0.904
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    0.296
_shelx_estimated_absorpt_T_min   0.866
_shelx_estimated_absorpt_T_max   0.904
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SHELXTL (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  120
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3971
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -2
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.193
_diffrn_reflns_theta_max         25.972
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2642
_reflns_number_gt                1696
_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       'Enraf-Nonius CAD4 Software package'
_computing_cell_refinement       'Enraf-Nonius CAD4 Software package'
_computing_data_reduction        'XCAD4PC (Harms, 1997)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0772P)²+0.2223P] 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_number_reflns         2642
_refine_ls_number_parameters     178
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1330
_refine_ls_wR_factor_gt          0.1150
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
Cl1 Cl 0.47732(9) 0.86802(9) 0.58731(4) 0.0562(3) Uani 1 1 d . . . . .
O1 O 0.78027(18) 0.9344(2) 0.34481(11) 0.0483(5) Uani 1 1 d . . . . .
O2 O 0.94917(17) 0.7661(2) 0.41015(10) 0.0475(5) Uani 1 1 d . . . . .
O3 O 0.91632(19) 0.5926(3) 0.25757(11) 0.0521(5) Uani 1 1 d . . . . .
O4 O 0.72845(17) 0.4229(2) 0.24353(10) 0.0453(5) Uani 1 1 d . . . . .
O5 O 0.8575(2) 0.4123(2) 0.47902(11) 0.0435(5) Uani 1 1 d . . . . .
H5 H 0.915(3) 0.373(4) 0.5089(19) 0.055(10) Uiso 1 1 d . . . . .
C1 C 0.7394(2) 0.6496(3) 0.32538(12) 0.0305(5) Uani 1 1 d . . . . .
C2 C 0.5761(2) 0.6703(3) 0.30696(13) 0.0359(6) Uani 1 1 d . . . . .
H2A H 0.5384 0.7753 0.3207 0.043 Uiso 1 1 calc R U . . .
H2B H 0.5188 0.6200 0.2594 0.043 Uiso 1 1 calc R U . . .
C3 C 0.6472(2) 0.5577(3) 0.37092(12) 0.0301(5) Uani 1 1 d . . . . .
H3A H 0.6336 0.4388 0.3585 0.036 Uiso 1 1 calc R U . . .
C4 C 0.8345(2) 0.7877(3) 0.36521(13) 0.0320(5) Uani 1 1 d . . . . .
C5 C 0.8691(3) 1.0733(4) 0.3803(2) 0.0666(9) Uani 1 1 d . . . . .
H5A H 0.8203 1.1758 0.3620 0.100 Uiso 1 1 calc R U . . .
H5B H 0.9608 1.0695 0.3667 0.100 Uiso 1 1 calc R U . . .
H5C H 0.8853 1.0668 0.4358 0.100 Uiso 1 1 calc R U . . .
C6 C 0.8056(2) 0.5542(3) 0.27261(13) 0.0325(5) Uani 1 1 d . . . . .
C7 C 0.7837(3) 0.3272(4) 0.18896(18) 0.0654(9) Uani 1 1 d . . . . .
H7A H 0.7260 0.2283 0.1751 0.098 Uiso 1 1 calc R U . . .
H7B H 0.8828 0.2965 0.2121 0.098 Uiso 1 1 calc R U . . .
H7C H 0.7792 0.3926 0.1432 0.098 Uiso 1 1 calc R U . . .
C8 C 0.6634(2) 0.5977(3) 0.45338(13) 0.0299(5) Uani 1 1 d . . . . .
C9 C 0.7741(2) 0.5187(3) 0.50749(13) 0.0327(5) Uani 1 1 d . . . . .
C10 C 0.7940(3) 0.5492(3) 0.58551(14) 0.0416(6) Uani 1 1 d . . . . .
H10A H 0.8694 0.4971 0.6215 0.050 Uiso 1 1 calc R U . . .
C11 C 0.7031(3) 0.6559(3) 0.61020(14) 0.0445(7) Uani 1 1 d . . . . .
H11A H 0.7151 0.6757 0.6630 0.053 Uiso 1 1 calc R U . . .
C12 C 0.5942(3) 0.7335(3) 0.55681(13) 0.0380(6) Uani 1 1 d . . . . .
C13 C 0.5741(2) 0.7048(3) 0.47905(12) 0.0330(5) Uani 1 1 d . . . . .
H13A H 0.4992 0.7585 0.4435 0.040 Uiso 1 1 calc R U . . .


_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
Cl1 C12 1.747(3) . ?
O1 C4 1.313(3) . ?
O1 C5 1.458(3) . ?
O2 C4 1.202(3) . ?
O3 C6 1.201(3) . ?
O4 C6 1.326(3) . ?
O4 C7 1.449(3) . ?
O5 C9 1.360(3) . ?
O5 H5 0.74(3) . ?
C1 C6 1.483(3) . ?
C1 C4 1.506(3) . ?
C1 C2 1.527(3) . ?
C1 C3 1.538(3) . ?
C2 C3 1.491(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C3 C8 1.485(3) . ?
C3 H3A 0.9900 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C8 C13 1.377(3) . ?
C8 C9 1.402(3) . ?
C9 C10 1.387(3) . ?
C10 C11 1.378(4) . ?
C10 H10A 0.9400 . ?
C11 C12 1.379(3) . ?
C11 H11A 0.9400 . ?
C12 C13 1.380(3) . ?
C13 H13A 0.9400 . ?

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
C4 O1 C5 115.4(2) . . ?
C6 O4 C7 115.6(2) . . ?
C9 O5 H5 114(3) . . ?
C6 C1 C4 112.62(19) . . ?
C6 C1 C2 119.94(19) . . ?
C4 C1 C2 119.23(19) . . ?
C6 C1 C3 118.8(2) . . ?
C4 C1 C3 117.92(18) . . ?
C2 C1 C3 58.21(14) . . ?
C3 C2 C1 61.27(15) . . ?
C3 C2 H2A 117.6 . . ?
C1 C2 H2A 117.6 . . ?
C3 C2 H2B 117.6 . . ?
C1 C2 H2B 117.6 . . ?
H2A C2 H2B 114.7 . . ?
C8 C3 C2 123.2(2) . . ?
C8 C3 C1 119.56(18) . . ?
C2 C3 C1 60.51(14) . . ?
C8 C3 H3A 114.4 . . ?
C2 C3 H3A 114.4 . . ?
C1 C3 H3A 114.4 . . ?
O2 C4 O1 123.4(2) . . ?
O2 C4 C1 123.7(2) . . ?
O1 C4 C1 112.91(19) . . ?
O1 C5 H5A 109.5 . . ?
O1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O3 C6 O4 123.9(2) . . ?
O3 C6 C1 123.6(2) . . ?
O4 C6 C1 112.56(19) . . ?
O4 C7 H7A 109.5 . . ?
O4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 118.9(2) . . ?
C13 C8 C3 123.57(19) . . ?
C9 C8 C3 117.5(2) . . ?
O5 C9 C10 123.1(2) . . ?
O5 C9 C8 116.4(2) . . ?
C10 C9 C8 120.5(2) . . ?
C11 C10 C9 119.9(2) . . ?
C11 C10 H10A 120.1 . . ?
C9 C10 H10A 120.1 . . ?
C10 C11 C12 119.5(2) . . ?
C10 C11 H11A 120.2 . . ?
C12 C11 H11A 120.2 . . ?
C11 C12 C13 121.0(2) . . ?
C11 C12 Cl1 120.02(19) . . ?
C13 C12 Cl1 118.94(19) . . ?
C8 C13 C12 120.2(2) . . ?
C8 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.057


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_S2e
_database_code_depnum_ccdc_archive 'CCDC 1818321'
_audit_update_record             
;
2018-01-20 deposited with the CCDC.
2018-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
Dimethyl 2-[5-bromo-3-methoxy-2-(methoxymethoxy)phenyl]cyclopropane-1,1-dicarboxylate
;
_chemical_name_common            ?
_chemical_melting_point_gt       371
_chemical_melting_point_lt       372
_chemical_formula_moiety         'C16 H19 Br O7'
_chemical_formula_sum            'C16 H19 Br O7'
_chemical_formula_weight         403.22

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   9.6172(5)
_cell_length_b                   18.6822(10)
_cell_length_c                   10.3451(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.3900(10)
_cell_angle_gamma                90
_cell_volume                     1753.28(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6500
_cell_measurement_theta_min      2.355
_cell_measurement_theta_max      25.577

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   0.450
_exptl_transmission_factor_max   0.797
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.378
_shelx_estimated_absorpt_T_min   0.450
_shelx_estimated_absorpt_T_max   0.797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16171
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.180
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3443
_reflns_number_gt                2894
_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       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0551P)²+0.5379P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         3443
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0924
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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 0.65951(3) 0.26046(2) 0.43012(3) 0.07374(14) Uani 1 1 d . . . . .
O1 O 0.1808(2) 0.32505(10) 0.51836(18) 0.0675(5) Uani 1 1 d . . . . .
O2 O 0.25395(18) 0.33959(8) 0.74389(15) 0.0495(4) Uani 1 1 d . . . . .
O3 O 0.0602(2) 0.46340(10) 0.7209(2) 0.0663(5) Uani 1 1 d . . . . .
O4 O 0.1936(2) 0.55477(9) 0.68912(19) 0.0578(4) Uani 1 1 d . . . . .
O5 O 0.86632(17) 0.38691(9) 0.90874(15) 0.0490(4) Uani 1 1 d . . . . .
O6 O 0.62481(17) 0.46560(8) 0.86532(14) 0.0441(3) Uani 1 1 d . . . . .
O7 O 0.6551(2) 0.58748(9) 0.83764(17) 0.0575(4) Uani 1 1 d . . . . .
C1 C 0.2393(2) 0.44254(11) 0.61244(19) 0.0345(4) Uani 1 1 d . . . . .
C2 C 0.2647(2) 0.47253(12) 0.4863(2) 0.0415(5) Uani 1 1 d . . . . .
H2A H 0.2631 0.4392 0.4139 0.050 Uiso 1 1 calc R U . . .
H2B H 0.2240 0.5194 0.4547 0.050 Uiso 1 1 calc R U . . .
C3 C 0.3928(2) 0.46913(11) 0.6156(2) 0.0351(4) Uani 1 1 d . . . . .
H3A H 0.4210 0.5156 0.6607 0.042 Uiso 1 1 calc R U . . .
C4 C 0.2189(2) 0.36321(11) 0.6163(2) 0.0373(4) Uani 1 1 d . . . . .
C5 C 0.2376(4) 0.26339(13) 0.7600(3) 0.0651(7) Uani 1 1 d . . . . .
H5A H 0.2644 0.2521 0.8557 0.098 Uiso 1 1 calc R U . . .
H5B H 0.3007 0.2378 0.7210 0.098 Uiso 1 1 calc R U . . .
H5C H 0.1370 0.2498 0.7140 0.098 Uiso 1 1 calc R U . . .
C6 C 0.1544(2) 0.48615(12) 0.6806(2) 0.0398(5) Uani 1 1 d . . . . .
C7 C 0.1176(3) 0.60282(15) 0.7526(3) 0.0682(8) Uani 1 1 d . . . . .
H7A H 0.1513 0.6509 0.7486 0.102 Uiso 1 1 calc R U . . .
H7B H 0.1377 0.5892 0.8465 0.102 Uiso 1 1 calc R U . . .
H7C H 0.0135 0.6003 0.7048 0.102 Uiso 1 1 calc R U . . .
C8 C 0.5180(2) 0.41866(10) 0.6377(2) 0.0337(4) Uani 1 1 d . . . . .
C9 C 0.5265(2) 0.37020(11) 0.5384(2) 0.0400(5) Uani 1 1 d . . . . .
H9A H 0.4498 0.3667 0.4554 0.048 Uiso 1 1 calc R U . . .
C10 C 0.6493(2) 0.32756(12) 0.5640(2) 0.0441(5) Uani 1 1 d . . . . .
C11 C 0.7679(2) 0.33145(12) 0.6846(2) 0.0430(5) Uani 1 1 d . . . . .
H11A H 0.8507 0.3028 0.6981 0.052 Uiso 1 1 calc R U . . .
C12 C 0.7601(2) 0.37907(11) 0.7845(2) 0.0388(5) Uani 1 1 d . . . . .
C13 C 0.6348(2) 0.42205(10) 0.76144(19) 0.0344(4) Uani 1 1 d . . . . .
C14 C 0.9967(2) 0.34441(15) 0.9367(3) 0.0563(6) Uani 1 1 d . . . . .
H14A H 1.0621 0.3546 1.0275 0.084 Uiso 1 1 calc R U . . .
H14B H 1.0449 0.3555 0.8715 0.084 Uiso 1 1 calc R U . . .
H14C H 0.9707 0.2946 0.9300 0.084 Uiso 1 1 calc R U . . .
C15 C 0.7242(3) 0.52522(13) 0.8986(3) 0.0542(6) Uani 1 1 d . . . . .
H15A H 0.7617 0.5315 0.9972 0.065 Uiso 1 1 calc R U . . .
H15B H 0.8073 0.5155 0.8678 0.065 Uiso 1 1 calc R U . . .
C16 C 0.5543(4) 0.61502(17) 0.8999(3) 0.0756(8) Uani 1 1 d . . . . .
H16A H 0.5130 0.6591 0.8561 0.113 Uiso 1 1 calc R U . . .
H16B H 0.6053 0.6236 0.9954 0.113 Uiso 1 1 calc R U . . .
H16C H 0.4767 0.5809 0.8900 0.113 Uiso 1 1 calc R U . . .


_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 C10 1.895(2) . ?
O1 C4 1.193(3) . ?
O2 C4 1.325(2) . ?
O2 C5 1.448(3) . ?
O3 C6 1.194(3) . ?
O4 C6 1.331(3) . ?
O4 C7 1.445(3) . ?
O5 C12 1.358(2) . ?
O5 C14 1.430(3) . ?
O6 C13 1.377(2) . ?
O6 C15 1.433(3) . ?
O7 C15 1.384(3) . ?
O7 C16 1.426(4) . ?
C1 C6 1.487(3) . ?
C1 C4 1.497(3) . ?
C1 C2 1.513(3) . ?
C1 C3 1.547(3) . ?
C2 C3 1.488(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C8 1.486(3) . ?
C3 H3A 0.9800 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.392(3) . ?
C8 C13 1.396(3) . ?
C9 C10 1.376(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.385(3) . ?
C11 C12 1.385(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.401(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C4 O2 C5 116.15(19) . . ?
C6 O4 C7 117.0(2) . . ?
C12 O5 C14 117.73(18) . . ?
C13 O6 C15 115.64(18) . . ?
C15 O7 C16 113.2(2) . . ?
C6 C1 C4 115.57(17) . . ?
C6 C1 C2 118.53(17) . . ?
C4 C1 C2 116.75(18) . . ?
C6 C1 C3 118.98(17) . . ?
C4 C1 C3 116.77(17) . . ?
C2 C1 C3 58.21(13) . . ?
C3 C2 C1 62.05(13) . . ?
C3 C2 H2A 117.6 . . ?
C1 C2 H2A 117.6 . . ?
C3 C2 H2B 117.6 . . ?
C1 C2 H2B 117.6 . . ?
H2A C2 H2B 114.7 . . ?
C8 C3 C2 123.50(18) . . ?
C8 C3 C1 121.19(17) . . ?
C2 C3 C1 59.74(13) . . ?
C8 C3 H3A 114.0 . . ?
C2 C3 H3A 114.0 . . ?
C1 C3 H3A 114.0 . . ?
O1 C4 O2 123.5(2) . . ?
O1 C4 C1 125.08(19) . . ?
O2 C4 C1 111.36(17) . . ?
O2 C5 H5A 109.5 . . ?
O2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O3 C6 O4 123.4(2) . . ?
O3 C6 C1 124.8(2) . . ?
O4 C6 C1 111.79(18) . . ?
O4 C7 H7A 109.5 . . ?
O4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 118.65(18) . . ?
C9 C8 C3 122.82(18) . . ?
C13 C8 C3 118.48(18) . . ?
C10 C9 C8 119.45(19) . . ?
C10 C9 H9A 120.3 . . ?
C8 C9 H9A 120.3 . . ?
C9 C10 C11 122.7(2) . . ?
C9 C10 Br1 119.46(16) . . ?
C11 C10 Br1 117.79(16) . . ?
C12 C11 C10 118.3(2) . . ?
C12 C11 H11A 120.9 . . ?
C10 C11 H11A 120.9 . . ?
O5 C12 C11 124.43(19) . . ?
O5 C12 C13 115.69(19) . . ?
C11 C12 C13 119.86(19) . . ?
O6 C13 C8 119.92(18) . . ?
O6 C13 C12 119.01(18) . . ?
C8 C13 C12 121.00(18) . . ?
O5 C14 H14A 109.5 . . ?
O5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O7 C15 O6 111.24(18) . . ?
O7 C15 H15A 109.4 . . ?
O6 C15 H15A 109.4 . . ?
O7 C15 H15B 109.4 . . ?
O6 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
O7 C16 H16A 109.5 . . ?
O7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O7 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_refine_diff_density_max         0.361
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.050


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
