# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_zq-tj
_database_code_depnum_ccdc_archive 'CCDC 1968793'
loop_
_audit_author_name
_audit_author_address
'Yi-Feng Wang'
;University of Science and Technology of China
China
;
_audit_update_record             
;
2019-11-28 deposited with the CCDC.	2020-03-23 downloaded from the CCDC.
;
_audit_creation_date             2019-07-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H19 Br O5'
_chemical_formula_sum            'C19 H19 Br O5'
_chemical_formula_weight         407.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 -0.6763 1.2805 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9606(3)
_cell_length_b                   9.9217(4)
_cell_length_c                   11.8105(4)
_cell_angle_alpha                72.290(3)
_cell_angle_beta                 88.750(3)
_cell_angle_gamma                63.972(4)
_cell_volume                     891.11(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4122
_cell_measurement_temperature    291(2)
_cell_measurement_theta_min      3.9520
_cell_measurement_theta_max      74.1550
_shelx_estimated_absorpt_T_max   0.498
_shelx_estimated_absorpt_T_min   0.452
_exptl_absorpt_coefficient_mu    3.376
_exptl_absorpt_correction_T_min  0.75159
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5844
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.077
_diffrn_reflns_theta_min         3.963
_diffrn_ambient_temperature      291(2)
_diffrn_detector_area_resol_mean 5.2169
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3315
_reflns_number_total             3476
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.638
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3476
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0299
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0431P)²+0.3198P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0795
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3), C14(H14), C13(H13), C11(H11), C10(H10)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.94241(3) -0.14109(3) 0.80200(2) 0.05049(9) Uani 1 1 d . . . . .
O2 O 0.7451(2) 0.42464(16) 0.48233(12) 0.0459(3) Uani 1 1 d . . . . .
O4 O 0.48844(17) 0.31511(17) 0.20718(14) 0.0463(3) Uani 1 1 d . . . . .
O1 O 0.8163(2) -0.18100(17) 0.59062(14) 0.0552(4) Uani 1 1 d . . . . .
C1 C 0.8497(2) 0.0121(2) 0.64781(16) 0.0357(4) Uani 1 1 d . . . . .
O5 O 0.87248(19) 0.93074(18) 0.08034(15) 0.0514(4) Uani 1 1 d . . . . .
C6 C 0.8358(2) 0.1624(2) 0.62849(16) 0.0373(4) Uani 1 1 d . . . . .
H6 H 0.8725 0.1879 0.6884 0.045 Uiso 1 1 calc R . . . .
C3 C 0.7258(2) 0.0852(2) 0.44649(17) 0.0374(4) Uani 1 1 d . . . . .
H3 H 0.6900 0.0605 0.3857 0.045 Uiso 1 1 calc R . . . .
C4 C 0.7098(2) 0.2363(2) 0.42630(16) 0.0333(3) Uani 1 1 d . . . . .
C2 C 0.7960(2) -0.0290(2) 0.55883(17) 0.0372(4) Uani 1 1 d . . . . .
O3 O 0.3545(2) 0.5474(2) 0.23876(19) 0.0663(5) Uani 1 1 d . . . . .
C15 C 0.4785(2) 0.4272(2) 0.25099(16) 0.0370(4) Uani 1 1 d . . . . .
C5 C 0.7650(2) 0.2722(2) 0.51626(16) 0.0353(4) Uani 1 1 d . . . . .
C7 C 0.6466(2) 0.3815(2) 0.31531(16) 0.0338(3) Uani 1 1 d . . . . .
H7 H 0.7301 0.3655 0.2593 0.041 Uiso 1 1 calc R . . . .
C9 C 0.6978(2) 0.6249(2) 0.29000(16) 0.0355(4) Uani 1 1 d . . . . .
C8 C 0.6391(2) 0.5108(2) 0.36602(16) 0.0372(4) Uani 1 1 d . . . . .
H8 H 0.5236 0.5712 0.3793 0.045 Uiso 1 1 calc R . . . .
C14 C 0.5866(2) 0.7827(2) 0.23542(19) 0.0411(4) Uani 1 1 d . . . . .
H14 H 0.4746 0.8183 0.2472 0.049 Uiso 1 1 calc R . . . .
C13 C 0.6385(2) 0.8896(2) 0.1633(2) 0.0441(4) Uani 1 1 d . . . . .
H13 H 0.5615 0.9952 0.1262 0.053 Uiso 1 1 calc R . . . .
C12 C 0.8060(2) 0.8376(2) 0.14698(17) 0.0387(4) Uani 1 1 d . . . . .
C11 C 0.9194(2) 0.6789(2) 0.2024(2) 0.0436(4) Uani 1 1 d . . . . .
H11 H 1.0320 0.6437 0.1924 0.052 Uiso 1 1 calc R . . . .
C10 C 0.8659(2) 0.5742(2) 0.27165(19) 0.0421(4) Uani 1 1 d . . . . .
H10 H 0.9425 0.4680 0.3069 0.051 Uiso 1 1 calc R . . . .
C19 C 0.7624(3) 1.0931(3) 0.0191(2) 0.0557(5) Uani 1 1 d . . . . .
H19A H 0.7123 1.1451 0.0764 0.084 Uiso 1 1 calc GR . . . .
H19B H 0.6764 1.1005 -0.0329 0.084 Uiso 1 1 calc GR . . . .
H19C H 0.8243 1.1434 -0.0275 0.084 Uiso 1 1 calc GR . . . .
C16 C 0.3338(3) 0.3386(3) 0.1485(2) 0.0534(5) Uani 1 1 d . . . . .
H16A H 0.2416 0.3876 0.1905 0.064 Uiso 1 1 calc R . . . .
H16B H 0.3419 0.2362 0.1532 0.064 Uiso 1 1 calc R . . . .
C18 C 0.7617(4) -0.2255(3) 0.5021(2) 0.0602(6) Uani 1 1 d . . . . .
H18A H 0.7803 -0.3336 0.5357 0.090 Uiso 1 1 calc GR . . . .
H18B H 0.8235 -0.2158 0.4352 0.090 Uiso 1 1 calc GR . . . .
H18C H 0.6444 -0.1573 0.4756 0.090 Uiso 1 1 calc GR . . . .
C17 C 0.2981(4) 0.4403(4) 0.0206(3) 0.0827(9) Uani 1 1 d . . . . .
H17A H 0.2773 0.5455 0.0160 0.124 Uiso 1 1 calc GR . . . .
H17B H 0.2013 0.4448 -0.0169 0.124 Uiso 1 1 calc GR . . . .
H17C H 0.3927 0.3963 -0.0198 0.124 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.8948(18) . ?
O2 C5 1.370(2) . ?
O2 C8 1.466(2) . ?
O4 C15 1.332(2) . ?
O4 C16 1.454(2) . ?
O1 C2 1.366(2) . ?
O1 C18 1.421(3) . ?
C1 C6 1.387(3) . ?
C1 C2 1.399(3) . ?
O5 C12 1.360(2) . ?
O5 C19 1.421(3) . ?
C6 C5 1.378(3) . ?
C3 C4 1.386(3) . ?
C3 C2 1.392(3) . ?
C4 C5 1.381(2) . ?
C4 C7 1.510(2) . ?
O3 C15 1.190(2) . ?
C15 C7 1.514(2) . ?
C7 C8 1.549(2) . ?
C9 C8 1.499(3) . ?
C9 C14 1.380(3) . ?
C9 C10 1.398(3) . ?
C14 C13 1.390(3) . ?
C13 C12 1.387(3) . ?
C12 C11 1.392(3) . ?
C11 C10 1.371(3) . ?
C16 C17 1.488(4) . ?

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 O2 C8 107.17(14) . . ?
C15 O4 C16 116.79(15) . . ?
C2 O1 C18 117.43(16) . . ?
C6 C1 Br1 118.06(13) . . ?
C6 C1 C2 122.56(17) . . ?
C2 C1 Br1 119.37(14) . . ?
C12 O5 C19 118.10(16) . . ?
C5 C6 C1 116.80(16) . . ?
C4 C3 C2 119.19(16) . . ?
C3 C4 C7 131.77(16) . . ?
C5 C4 C3 120.30(17) . . ?
C5 C4 C7 107.86(15) . . ?
O1 C2 C1 116.27(16) . . ?
O1 C2 C3 124.88(17) . . ?
C3 C2 C1 118.84(16) . . ?
O4 C15 C7 110.54(15) . . ?
O3 C15 O4 124.10(18) . . ?
O3 C15 C7 125.35(17) . . ?
O2 C5 C6 123.94(16) . . ?
O2 C5 C4 113.74(16) . . ?
C6 C5 C4 122.31(17) . . ?
C4 C7 C15 115.30(15) . . ?
C4 C7 C8 101.96(14) . . ?
C15 C7 C8 111.65(15) . . ?
C14 C9 C8 120.68(16) . . ?
C14 C9 C10 118.28(17) . . ?
C10 C9 C8 121.04(17) . . ?
O2 C8 C7 105.64(14) . . ?
O2 C8 C9 109.20(15) . . ?
C9 C8 C7 115.67(15) . . ?
C9 C14 C13 121.43(17) . . ?
C12 C13 C14 119.51(18) . . ?
O5 C12 C13 125.09(18) . . ?
O5 C12 C11 115.41(17) . . ?
C13 C12 C11 119.50(18) . . ?
C10 C11 C12 120.35(17) . . ?
C11 C10 C9 120.91(18) . . ?
O4 C16 C17 111.9(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
