# 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_ylw1908b
_database_code_depnum_ccdc_archive 'CCDC 1949875'
loop_
_audit_author_name
_audit_author_address
'Yi-Lin Wu'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2019-08-28 deposited with the CCDC.	2020-11-05 downloaded from the CCDC.
;
_audit_creation_date             2019-08-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'tetraethyl naphthalene-1,4,5,8-tetracarboxylate'
_chemical_formula_moiety         'C22 H24 O8'
_chemical_formula_sum            'C22 H24 O8'
_chemical_formula_weight         416.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c14 h12 O8 Br2'
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   8.5666(7)
_cell_length_b                   14.3257(7)
_cell_length_c                   9.2306(8)
_cell_angle_alpha                90
_cell_angle_beta                 112.196(10)
_cell_angle_gamma                90
_cell_volume                     1048.86(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2812
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.0460
_cell_measurement_theta_min      3.9470
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45b (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             440
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
7 4 7 0.0628
1 -10 -11 0.0597
-10 -9 -1 0.0682
-4 19 1 0.1155
6 3 8 0.0561
3 -19 2 0.1066
10 0 -11 0.1035
-10 0 11 0.1035
1 9 -11 0.1019
5 18 -4 0.1376

_exptl_crystal_size_max          0.249
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.163
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
7.0083 3.9552 6.9799 -0.4200 -0.8963 -0.2484
0.9943 -9.9566 -10.9993 0.0750 0.5946 0.8150
-9.9985 -8.9693 -0.9847 0.8343 0.5878 0.1328
-4.0142 18.9988 1.0262 -0.3214 0.4378 -0.8382
6.0099 2.9541 7.9801 -0.3169 -0.9181 -0.2735
3.0175 -19.0079 1.9727 0.4247 -0.5903 0.6997
9.9904 0.0185 -11.0102 -0.7462 0.1560 0.6594
-9.9904 -0.0185 11.0102 0.7462 -0.1560 -0.6594
0.9804 9.0365 -10.9811 -0.4935 0.8498 0.1106
4.9839 17.9970 -3.9895 -0.8890 0.2116 -0.3949

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.846
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8629
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.846
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.746
_diffrn_reflns_theta_min         3.711
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5082
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.846
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -76.00  29.00   1.00   32.63    --  -11.05   0.00-120.00  105
  2  ω     52.00  77.00   1.00   32.63    --  -11.05   0.00-120.00   25
  3  ω    -96.00  77.00   1.00   32.63    --  -11.05   0.00  90.00  173
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0580206000
_diffrn_orient_matrix_UB_12      -0.0299892000
_diffrn_orient_matrix_UB_13      0.0150805000
_diffrn_orient_matrix_UB_21      -0.0637707000
_diffrn_orient_matrix_UB_22      0.0134575000
_diffrn_orient_matrix_UB_23      -0.0720062000
_diffrn_orient_matrix_UB_31      0.0237209000
_diffrn_orient_matrix_UB_32      -0.0370312000
_diffrn_orient_matrix_UB_33      -0.0384281000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1769
_reflns_number_total             2519
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.706
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2519
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0779
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1291P)²+0.7560P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2365
_refine_ls_wR_factor_ref         0.2609
_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 Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O3 O 0.1094(3) 0.40862(14) 0.2558(3) 0.0567(6) Uani 1 1 d . . . . .
O4 O 0.1562(3) 0.27533(15) 0.3992(3) 0.0670(7) Uani 1 1 d . . . . .
O1 O 0.6006(3) 0.68138(15) 0.7807(3) 0.0628(6) Uani 1 1 d . . . . .
O2 O 0.7018(4) 0.57884(19) 0.9760(3) 0.0751(8) Uani 1 1 d . . . . .
C5 C 0.4454(3) 0.46868(16) 0.4419(3) 0.0395(6) Uani 1 1 d . . . . .
C4 C 0.3484(3) 0.40302(17) 0.4888(3) 0.0446(6) Uani 1 1 d . . . . .
C1 C 0.5622(3) 0.52352(19) 0.7151(3) 0.0461(6) Uani 1 1 d . . . . .
C3 C 0.3748(4) 0.3923(2) 0.6439(3) 0.0520(7) Uani 1 1 d . . . . .
H3 H 0.320432 0.344370 0.674281 0.062 Uiso 1 1 calc R . . . .
C2 C 0.4819(4) 0.4519(2) 0.7564(3) 0.0519(7) Uani 1 1 d . . . . .
H2 H 0.499126 0.443057 0.861100 0.062 Uiso 1 1 calc R . . . .
C9 C 0.1977(4) 0.3534(2) 0.3766(4) 0.0532(7) Uani 1 1 d . . . . .
C6 C 0.6329(4) 0.5962(2) 0.8386(4) 0.0560(7) Uani 1 1 d . . . . .
C10 C -0.0483(4) 0.3721(3) 0.1421(4) 0.0649(8) Uani 1 1 d . . . . .
H10A H -0.034381 0.306583 0.123220 0.078 Uiso 1 1 calc R . . . .
H10B H -0.076476 0.405221 0.043823 0.078 Uiso 1 1 calc R . . . .
C11 C -0.1868(5) 0.3826(3) 0.1986(5) 0.0774(11) Uani 1 1 d . . . . .
H11A H -0.291223 0.364805 0.117307 0.116 Uiso 1 1 calc GR . . . .
H11B H -0.193346 0.446454 0.227206 0.116 Uiso 1 1 calc GR . . . .
H11C H -0.165936 0.343275 0.288264 0.116 Uiso 1 1 calc GR . . . .
C7 C 0.6524(6) 0.7568(3) 0.8971(5) 0.0824(12) Uani 1 1 d . . . . .
H7A H 0.600490 0.748478 0.973174 0.099 Uiso 1 1 calc R . . . .
H7B H 0.773849 0.756374 0.951870 0.099 Uiso 1 1 calc R . . . .
C8 C 0.5989(7) 0.8441(3) 0.8151(6) 0.1040(16) Uani 1 1 d . . . . .
H8A H 0.651831 0.851945 0.740978 0.156 Uiso 1 1 calc GR . . . .
H8B H 0.630612 0.894649 0.888841 0.156 Uiso 1 1 calc GR . . . .
H8C H 0.478654 0.843711 0.761109 0.156 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
O3 C9 1.343(4) . ?
O3 C10 1.459(4) . ?
O4 C9 1.215(4) . ?
O1 C6 1.320(4) . ?
O1 C7 1.469(4) . ?
O2 C6 1.205(4) . ?
C5 C5 1.439(5) 3_666 ?
C5 C4 1.427(4) . ?
C5 C1 1.430(3) 3_666 ?
C4 C3 1.371(4) . ?
C4 C9 1.495(4) . ?
C1 C2 1.367(4) . ?
C1 C6 1.493(4) . ?
C3 C2 1.389(4) . ?
C10 C11 1.473(5) . ?
C7 C8 1.443(6) . ?

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
C9 O3 C10 117.6(2) . . ?
C6 O1 C7 115.2(3) . . ?
C4 C5 C5 118.2(3) . 3_666 ?
C4 C5 C1 123.4(2) . 3_666 ?
C1 C5 C5 118.4(3) 3_666 3_666 ?
C5 C4 C9 123.6(2) . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 C9 115.4(2) . . ?
C5 C1 C6 124.7(2) 3_666 . ?
C2 C1 C5 120.4(2) . 3_666 ?
C2 C1 C6 114.3(2) . . ?
C4 C3 C2 120.9(3) . . ?
C1 C2 C3 120.9(2) . . ?
O3 C9 C4 111.3(2) . . ?
O4 C9 O3 125.1(3) . . ?
O4 C9 C4 123.4(3) . . ?
O1 C6 C1 111.9(2) . . ?
O2 C6 O1 124.1(3) . . ?
O2 C6 C1 123.8(3) . . ?
O3 C10 C11 111.1(3) . . ?
C8 C7 O1 107.8(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.477
_oxdiff_exptl_absorpt_empirical_full_min 0.845
####################################################################### 
# 
# 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_ylw1902b
_database_code_depnum_ccdc_archive 'CCDC 1949883'
loop_
_audit_author_name
_audit_author_address
'Yi-Lin Wu'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2019-08-28 deposited with the CCDC.	2020-11-05 downloaded from the CCDC.
;
_audit_creation_date             2019-08-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'tetraethyl 2,3,6,7-tetrabromonaphthalene-1,4,5,8-tetracarboxylate'
_chemical_formula_moiety         '2(C11 H10 Br2 O4)'
_chemical_formula_sum            'C22 H20 Br4 O8'
_chemical_formula_weight         732.02
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H12 n o Br'
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'

_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                   9.5351(5)
_cell_length_b                   12.0414(6)
_cell_length_c                   12.8133(8)
_cell_angle_alpha                72.585(5)
_cell_angle_beta                 69.310(5)
_cell_angle_gamma                89.363(4)
_cell_volume                     1305.80(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3019
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.5960
_cell_measurement_theta_min      4.1630
_shelx_estimated_absorpt_T_max   0.624
_shelx_estimated_absorpt_T_min   0.306
_exptl_absorpt_coefficient_mu    6.207
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.632
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.862
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -2 -17 0.0352
2 2 17 0.0492
-9 -12 -10 0.1012
11 9 10 0.0557
11 -9 1 0.0571
-11 9 0 0.0709

_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.084
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.9952 -1.9964 -17.0024 -0.7933 -0.5761 0.0313
1.9952 1.9964 17.0024 0.7933 0.5761 -0.0313
-9.0022 -12.0032 -9.9981 -0.7166 0.4902 0.4468
11.0026 9.0009 9.9976 0.7730 -0.5534 -0.2304
11.0031 -9.0081 0.9970 0.3630 -0.4962 0.7684
-11.0035 9.0079 0.0032 -0.3201 0.5414 -0.7663

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.819
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10370
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.855
_diffrn_reflns_theta_min         3.392
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5082
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.819
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -78.00  14.00   1.00   19.42    --  -11.21 -57.00  60.00   92
  2  ω    -74.00  19.00   1.00   19.42    --  -11.21 -77.00 -60.00   93
  3  ω    -36.00  61.00   1.00   19.42    --  -11.21  57.00-150.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0301576000
_diffrn_orient_matrix_UB_12      0.0012933000
_diffrn_orient_matrix_UB_13      0.0429650000
_diffrn_orient_matrix_UB_21      -0.0702673000
_diffrn_orient_matrix_UB_22      -0.0257481000
_diffrn_orient_matrix_UB_23      0.0451549000
_diffrn_orient_matrix_UB_31      0.0234067000
_diffrn_orient_matrix_UB_32      -0.0564789000
_diffrn_orient_matrix_UB_33      0.0020430000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4079
_reflns_number_total             6162
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.743
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         6162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0286P)²+1.1870P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0937
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C10(H10A,H10B), C18(H18A,H18B), C21(H21A,H21B)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C11(H11A,H11B,H11C), C19(H19A,H19B,H19C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.59947(5) 0.15421(4) 0.45007(4) 0.06095(14) Uani 1 1 d . . . . .
Br2 Br 0.54511(5) 0.03157(5) 0.72813(5) 0.07574(17) Uani 1 1 d . . . . .
O1 O 0.9521(3) 0.2624(2) 0.2685(3) 0.0598(8) Uani 1 1 d . . . . .
O2 O 0.8894(4) 0.1154(3) 0.2132(3) 0.0677(9) Uani 1 1 d . . . . .
O3 O 0.8447(4) 0.0266(3) 0.8086(2) 0.0619(8) Uani 1 1 d . . . . .
O4 O 0.7632(3) -0.1595(3) 0.8419(3) 0.0593(8) Uani 1 1 d . . . . .
C1 C 0.8455(4) -0.0212(3) 0.6469(3) 0.0397(8) Uani 1 1 d . . . . .
C2 C 0.7319(4) 0.0270(3) 0.6124(4) 0.0454(9) Uani 1 1 d . . . . .
C3 C 0.7550(4) 0.0783(3) 0.4930(4) 0.0451(9) Uani 1 1 d . . . . .
C4 C 0.8920(4) 0.0805(3) 0.4078(3) 0.0392(8) Uani 1 1 d . . . . .
C5 C 1.0121(4) 0.0260(3) 0.4393(3) 0.0357(8) Uani 1 1 d . . . . .
C6 C 0.9110(4) 0.1519(4) 0.2836(4) 0.0488(10) Uani 1 1 d . . . . .
C7 C 0.9708(7) 0.3474(4) 0.1554(5) 0.0859(17) Uani 1 1 d . . . . .
H7A H 0.884986 0.337634 0.133822 0.103 Uiso 1 1 calc R . . . .
H7B H 1.061398 0.337878 0.094716 0.103 Uiso 1 1 calc R . . . .
C8 C 0.9822(10) 0.4642(5) 0.1696(7) 0.142(3) Uani 1 1 d . . . . .
H8A H 0.961968 0.521969 0.107913 0.214 Uiso 1 1 calc GR . . . .
H8B H 1.081893 0.482731 0.165765 0.214 Uiso 1 1 calc GR . . . .
H8C H 0.909981 0.463582 0.244398 0.214 Uiso 1 1 calc GR . . . .
C9 C 0.8138(4) -0.0625(4) 0.7770(4) 0.0465(9) Uani 1 1 d . . . . .
C10 C 0.8109(8) 0.0031(5) 0.9345(4) 0.0964(19) Uani 1 1 d . . . . .
H10A H 0.719909 -0.050728 0.979616 0.116 Uiso 1 1 calc R . . . .
H10B H 0.892964 -0.032994 0.955081 0.116 Uiso 1 1 calc R . . . .
C11 C 0.7908(8) 0.1089(7) 0.9625(6) 0.124(3) Uani 1 1 d . . . . .
H11A H 0.877868 0.164212 0.913229 0.187 Uiso 1 1 calc GR . . . .
H11B H 0.777931 0.093803 1.043414 0.187 Uiso 1 1 calc GR . . . .
H11C H 0.703126 0.140237 0.949704 0.187 Uiso 1 1 calc GR . . . .
Br3 Br 0.20296(5) 0.18263(4) 0.74251(4) 0.06627(15) Uani 1 1 d . . . . .
Br4 Br 0.36868(6) 0.30335(5) 0.87509(4) 0.06932(16) Uani 1 1 d . . . . .
O5 O 0.4796(3) 0.5894(3) 0.7691(3) 0.0616(8) Uani 1 1 d . . . . .
O6 O 0.6925(3) 0.5023(3) 0.7278(3) 0.0653(8) Uani 1 1 d . . . . .
O7 O 0.1266(3) 0.3559(2) 0.5239(3) 0.0526(7) Uani 1 1 d . . . . .
O8 O 0.2984(3) 0.2453(2) 0.4460(3) 0.0553(7) Uani 1 1 d . . . . .
C12 C 0.3573(4) 0.3725(3) 0.5418(3) 0.0389(8) Uani 1 1 d . . . . .
C13 C 0.3346(4) 0.3220(3) 0.6575(3) 0.0418(9) Uani 1 1 d . . . . .
C14 C 0.4090(4) 0.3724(3) 0.7124(3) 0.0426(9) Uani 1 1 d . . . . .
C15 C 0.5060(4) 0.4729(3) 0.6504(3) 0.0384(8) Uani 1 1 d . . . . .
C16 C 0.5380(4) 0.5255(3) 0.5281(3) 0.0350(8) Uani 1 1 d . . . . .
C17 C 0.5735(5) 0.5233(4) 0.7192(4) 0.0489(10) Uani 1 1 d . . . . .
C18 C 0.5343(6) 0.6442(6) 0.8378(5) 0.0917(19) Uani 1 1 d . . . . .
H18A H 0.580988 0.588076 0.883637 0.110 Uiso 1 1 calc R . . . .
H18B H 0.609072 0.709952 0.785413 0.110 Uiso 1 1 calc R . . . .
C19 C 0.4100(7) 0.6831(7) 0.9134(6) 0.120(3) Uani 1 1 d . . . . .
H19A H 0.367709 0.741598 0.867261 0.179 Uiso 1 1 calc GR . . . .
H19B H 0.443361 0.716010 0.961397 0.179 Uiso 1 1 calc GR . . . .
H19C H 0.334949 0.618153 0.962858 0.179 Uiso 1 1 calc GR . . . .
C20 C 0.2601(4) 0.3170(3) 0.4948(3) 0.0421(9) Uani 1 1 d . . . . .
C21 C 0.0149(5) 0.3038(5) 0.4932(5) 0.0762(16) Uani 1 1 d . . . . .
H21A H 0.041384 0.330954 0.408625 0.091 Uiso 1 1 calc R . . . .
H21B H 0.012698 0.219211 0.518679 0.091 Uiso 1 1 calc R . . . .
C22 C -0.1302(6) 0.3372(6) 0.5500(7) 0.121(3) Uani 1 1 d . . . . .
H22A H -0.127504 0.420903 0.523565 0.181 Uiso 1 1 calc GR . . . .
H22B H -0.155697 0.309920 0.633567 0.181 Uiso 1 1 calc GR . . . .
H22C H -0.204548 0.303085 0.530780 0.181 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 C3 1.893(4) . ?
Br2 C2 1.886(4) . ?
O1 C6 1.329(5) . ?
O1 C7 1.454(5) . ?
O2 C6 1.191(5) . ?
O3 C9 1.323(5) . ?
O3 C10 1.466(5) . ?
O4 C9 1.198(5) . ?
C1 C2 1.370(5) . ?
C1 C5 1.429(5) 2_756 ?
C1 C9 1.507(5) . ?
C2 C3 1.403(5) . ?
C3 C4 1.369(5) . ?
C4 C5 1.434(5) . ?
C4 C6 1.511(5) . ?
C5 C5 1.426(7) 2_756 ?
C7 C8 1.481(8) . ?
C10 C11 1.416(8) . ?
Br3 C13 1.888(4) . ?
Br4 C14 1.895(4) . ?
O5 C17 1.315(5) . ?
O5 C18 1.470(5) . ?
O6 C17 1.195(5) . ?
O7 C20 1.317(4) . ?
O7 C21 1.463(5) . ?
O8 C20 1.194(4) . ?
C12 C13 1.360(5) . ?
C12 C16 1.430(5) 2_666 ?
C12 C20 1.522(5) . ?
C13 C14 1.409(5) . ?
C14 C15 1.371(5) . ?
C15 C16 1.422(5) . ?
C15 C17 1.514(5) . ?
C16 C16 1.436(7) 2_666 ?
C18 C19 1.418(7) . ?
C21 C22 1.434(7) . ?

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
C6 O1 C7 116.8(3) . . ?
C9 O3 C10 116.2(4) . . ?
C2 C1 C5 120.0(3) . 2_756 ?
C2 C1 C9 116.8(3) . . ?
C5 C1 C9 123.1(3) 2_756 . ?
C1 C2 Br2 119.0(3) . . ?
C1 C2 C3 121.2(4) . . ?
C3 C2 Br2 119.7(3) . . ?
C2 C3 Br1 119.6(3) . . ?
C4 C3 Br1 119.7(3) . . ?
C4 C3 C2 120.6(3) . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 C6 116.2(3) . . ?
C5 C4 C6 123.3(3) . . ?
C1 C5 C4 122.2(3) 2_756 . ?
C5 C5 C1 119.0(4) 2_756 2_756 ?
C5 C5 C4 118.8(4) 2_756 . ?
O1 C6 C4 107.8(3) . . ?
O2 C6 O1 126.4(4) . . ?
O2 C6 C4 125.8(4) . . ?
O1 C7 C8 106.2(5) . . ?
O3 C9 C1 109.1(3) . . ?
O4 C9 O3 125.7(4) . . ?
O4 C9 C1 125.1(4) . . ?
C11 C10 O3 110.0(5) . . ?
C17 O5 C18 114.3(3) . . ?
C20 O7 C21 115.5(3) . . ?
C13 C12 C16 121.0(3) . 2_666 ?
C13 C12 C20 115.9(3) . . ?
C16 C12 C20 123.1(3) 2_666 . ?
C12 C13 Br3 118.8(3) . . ?
C12 C13 C14 120.5(3) . . ?
C14 C13 Br3 120.7(3) . . ?
C13 C14 Br4 119.4(3) . . ?
C15 C14 Br4 119.8(3) . . ?
C15 C14 C13 120.8(3) . . ?
C14 C15 C16 120.4(3) . . ?
C14 C15 C17 116.5(3) . . ?
C16 C15 C17 123.0(3) . . ?
C12 C16 C16 118.3(4) 2_666 2_666 ?
C15 C16 C12 122.8(3) . 2_666 ?
C15 C16 C16 118.9(4) . 2_666 ?
O5 C17 C15 109.4(3) . . ?
O6 C17 O5 126.5(4) . . ?
O6 C17 C15 124.0(4) . . ?
C19 C18 O5 108.5(5) . . ?
O7 C20 C12 108.6(3) . . ?
O8 C20 O7 126.8(3) . . ?
O8 C20 C12 124.5(3) . . ?
C22 C21 O7 108.7(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.788
_oxdiff_exptl_absorpt_empirical_full_min 0.709
####################################################################### 
# 
# 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_ylw1906c
_database_code_depnum_ccdc_archive 'CCDC 1949880'
loop_
_audit_author_name
_audit_author_address
'Yi-Lin Wu'
;Cardiff University
United Kingdom
;
_audit_update_record             
;
2019-08-28 deposited with the CCDC.	2020-11-05 downloaded from the CCDC.
;
_audit_creation_date             2019-08-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'tetraethyl 2-bromonaphthalene-1,4,5,8-tetracarboxylate'
_chemical_formula_moiety         'C22 H23 Br O8'
_chemical_formula_sum            'C22 H23 Br O8'
_chemical_formula_weight         495.31
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 h12 n2 o2'
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'

_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.6364(5)
_cell_length_b                   9.8092(5)
_cell_length_c                   11.8602(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.442(4)
_cell_angle_gamma                90
_cell_volume                     1121.06(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4036
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.7890
_cell_measurement_theta_min      4.0070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.878
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             508
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 11 -10 0.0425
-9 -9 -7 0.0788
7 11 -5 0.0558
2 -13 4 0.0534
-13 -2 0 0.1006
0 -10 -11 0.0510
0 10 11 0.0510
12 -5 4 0.0577
-2 7 14 0.0534

_exptl_crystal_size_max          0.193
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.102
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.9938 11.0056 -9.9972 0.4423 -0.7593 -0.4923
-9.0000 -8.9920 -7.0011 -0.0602 0.6777 -0.7603
7.0042 10.9960 -4.9948 0.0539 -0.9880 0.0803
1.9949 -13.0052 4.0000 -0.6364 0.7309 0.1592
-12.9997 -1.9875 -0.0066 0.5916 0.6069 -0.4667
0.0003 -10.0006 -10.9946 -0.6476 0.2964 -0.6690
-0.0003 10.0006 10.9946 0.6476 -0.2964 0.6690
11.9966 -5.0134 4.0047 -0.7937 -0.0914 0.5776
-2.0019 7.0015 13.9924 0.6655 0.0142 0.7298

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10647
_diffrn_reflns_point_group_measured_fraction_full 0.814
_diffrn_reflns_point_group_measured_fraction_max 0.659
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.542
_diffrn_reflns_theta_min         3.417
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5082
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ    123.00 227.00   1.00   42.10  10.82  10.82  40.00    --   104
  2  φ    128.00 240.00   1.00   42.10  10.82  10.82  60.00    --   112
  3  φ    120.00 168.00   1.00   42.10  40.00  10.82   0.00    --    48
  4  φ    240.00 300.00   1.00   42.10  10.82  10.82  60.00    --    60
  5  φ    319.00 360.00   1.00   42.10  10.82  10.82 -40.00    --    41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0525647000
_diffrn_orient_matrix_UB_12      0.0460923000
_diffrn_orient_matrix_UB_13      0.0169771000
_diffrn_orient_matrix_UB_21      -0.0382906000
_diffrn_orient_matrix_UB_22      -0.0549878000
_diffrn_orient_matrix_UB_23      0.0230524000
_diffrn_orient_matrix_UB_31      0.0344688000
_diffrn_orient_matrix_UB_32      0.0091913000
_diffrn_orient_matrix_UB_33      0.0524891000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.418
_reflns_Friedel_fraction_full    0.610
_reflns_Friedel_fraction_max     0.411
_reflns_number_gt                3341
_reflns_number_total             4142
_reflns_odcompleteness_completeness 99.42
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45b (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.079
_refine_ls_abs_structure_details 
;
 Flack x determined using 984 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.339(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4142
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0677
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0300P)²+3.7620P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1502
_refine_ls_wR_factor_ref         0.1610
_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. Others
 Sof(H2)=Sof(Br1)=1-FVAR(1)
 Sof(Br01)=Sof(H7)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C21(H21A,H21B), C15(H15A,H15B), C18(H18A,H18B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C2(H2)
3.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C13(H13A,H13B,H13C), C16(H16A,H16B,H16C), C22(H22A,H22B,
 H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Br01 Br 1.04605(18) 0.19426(15) 0.60924(11) 0.0659(6) Uani 0.686(3) 1 d . . P A
1
O3 O 1.0606(7) 0.4984(9) 0.9846(5) 0.057(2) Uani 1 1 d . . . . .
O5 O 0.6211(7) 0.6103(10) 1.0601(5) 0.070(2) Uani 1 1 d . . . . .
O2 O 0.6791(7) 0.2651(7) 0.4945(5) 0.0543(17) Uani 1 1 d . . . . .
O4 O 0.8613(8) 0.4111(9) 1.0524(5) 0.068(2) Uani 1 1 d . . . . .
C4 C 0.8938(9) 0.4445(10) 0.8533(6) 0.042(2) Uani 1 1 d . . . . .
O6 O 0.8234(7) 0.7035(9) 1.0044(5) 0.067(2) Uani 1 1 d . . . . .
C14 C 0.9361(10) 0.4524(11) 0.9723(6) 0.047(2) Uani 1 1 d . . . . .
C10 C 0.7306(9) 0.4742(9) 0.6911(7) 0.041(2) Uani 1 1 d . . . . .
O7 O 0.4417(7) 0.4711(8) 0.5119(6) 0.061(2) Uani 1 1 d . . . . .
O8 O 0.6378(7) 0.5599(7) 0.4496(5) 0.0551(18) Uani 1 1 d . . . . .
O1 O 0.8721(7) 0.3721(8) 0.4374(5) 0.0551(17) Uani 1 1 d . . . . .
C1 C 0.8186(10) 0.3810(9) 0.6306(7) 0.042(2) Uani 1 1 d . . . . .
C17 C 0.7173(11) 0.6432(12) 0.9840(8) 0.061(3) Uani 1 1 d . . . . .
C12 C 0.8447(12) 0.3329(12) 0.3231(7) 0.058(3) Uani 1 1 d . . . . .
H12A H 0.888585 0.397535 0.272746 0.070 Uiso 1 1 calc R . . . .
H12B H 0.745478 0.336041 0.308999 0.070 Uiso 1 1 calc R . . . .
C3 C 0.9753(10) 0.3618(10) 0.7898(7) 0.047(2) Uani 1 1 d . . . . .
H3 H 1.056340 0.325779 0.820636 0.057 Uiso 1 1 calc R . . . .
C11 C 0.7814(9) 0.3350(9) 0.5138(7) 0.0412(19) Uani 1 1 d . . . . .
C7 C 0.5587(10) 0.6393(10) 0.8224(8) 0.053(2) Uani 1 1 d . . . . .
H7 H 0.500607 0.695286 0.864264 0.064 Uiso 0.686(3) 1 calc R . P A 10
C8 C 0.5251(11) 0.6092(11) 0.7097(8) 0.056(3) Uani 1 1 d . . . . .
H8 H 0.443016 0.642630 0.678541 0.068 Uiso 1 1 calc R . . . .
C2 C 0.9378(10) 0.3304(11) 0.6778(7) 0.052(2) Uani 1 1 d . . . . .
H2 H 0.995099 0.274435 0.635282 0.062 Uiso 0.314(3) 1 calc R . P A 2
C21 C 0.3904(12) 0.4619(13) 0.3960(8) 0.067(3) Uani 1 1 d . . . . .
H21A H 0.450686 0.404656 0.351108 0.080 Uiso 1 1 calc R . . . .
H21B H 0.385711 0.551590 0.361732 0.080 Uiso 1 1 calc R . . . .
C6 C 0.6765(9) 0.5868(10) 0.8711(7) 0.046(2) Uani 1 1 d . . . . .
C5 C 0.7656(8) 0.5030(9) 0.8050(7) 0.0384(19) Uani 1 1 d . . . . .
C20 C 0.5693(10) 0.5205(11) 0.5197(9) 0.051(2) Uani 1 1 d . . . . .
C19 C 0.6050(19) 0.7889(18) 1.1967(12) 0.114(6) Uani 1 1 d . . . . .
H19A H 0.645548 0.846648 1.140547 0.172 Uiso 1 1 calc GR . . . .
H19B H 0.635923 0.817213 1.270169 0.172 Uiso 1 1 calc GR . . . .
H19C H 0.505664 0.795468 1.192232 0.172 Uiso 1 1 calc GR . . . .
C13 C 0.8982(13) 0.1896(18) 0.2971(10) 0.101(5) Uani 1 1 d . . . . .
H13A H 0.851652 0.154896 0.231292 0.152 Uiso 1 1 calc GR . . . .
H13B H 0.880253 0.130766 0.360052 0.152 Uiso 1 1 calc GR . . . .
H13C H 0.996267 0.193163 0.283815 0.152 Uiso 1 1 calc GR . . . .
C15 C 1.1159(12) 0.5074(16) 1.0989(9) 0.076(4) Uani 1 1 d . . . . .
H15A H 1.127900 0.417161 1.130998 0.091 Uiso 1 1 calc R . . . .
H15B H 1.053874 0.559196 1.146599 0.091 Uiso 1 1 calc R . . . .
C16 C 1.2511(13) 0.5772(19) 1.0890(12) 0.105(5) Uani 1 1 d . . . . .
H16A H 1.239699 0.659215 1.045760 0.157 Uiso 1 1 calc GR . . . .
H16B H 1.315832 0.518145 1.051905 0.157 Uiso 1 1 calc GR . . . .
H16C H 1.285727 0.599519 1.162818 0.157 Uiso 1 1 calc GR . . . .
C9 C 0.6113(10) 0.5316(10) 0.6454(7) 0.044(2) Uani 1 1 d . . . . .
C22 C 0.2467(13) 0.3996(18) 0.4038(11) 0.101(5) Uani 1 1 d . . . . .
H22A H 0.206654 0.392613 0.329721 0.151 Uiso 1 1 calc GR . . . .
H22B H 0.189167 0.456376 0.449979 0.151 Uiso 1 1 calc GR . . . .
H22C H 0.253444 0.310478 0.436839 0.151 Uiso 1 1 calc GR . . . .
C18 C 0.6447(15) 0.6560(18) 1.1783(11) 0.096(5) Uani 1 1 d . . . . .
H18A H 0.593394 0.596926 1.228571 0.115 Uiso 1 1 calc R . . . .
H18B H 0.742504 0.646728 1.196611 0.115 Uiso 1 1 calc R . . . .
Br1 Br 0.4540(3) 0.7785(3) 0.8903(2) 0.0543(12) Uani 0.314(3) 1 d . . P A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br01 C2 1.883(10) . ?
O3 C14 1.289(11) . ?
O3 C15 1.455(11) . ?
O5 C17 1.339(12) . ?
O5 C18 1.487(14) . ?
O2 C11 1.222(10) . ?
O4 C14 1.264(12) . ?
C4 C14 1.468(10) . ?
C4 C3 1.360(12) . ?
C4 C5 1.474(12) . ?
O6 C17 1.204(12) . ?
C10 C1 1.442(12) . ?
C10 C5 1.419(8) . ?
C10 C9 1.386(13) . ?
O7 C21 1.461(11) . ?
O7 C20 1.323(11) . ?
O8 C20 1.133(11) . ?
O1 C12 1.432(10) . ?
O1 C11 1.315(10) . ?
C1 C11 1.498(11) . ?
C1 C2 1.367(12) . ?
C17 C6 1.498(13) . ?
C12 C13 1.53(2) . ?
C3 C2 1.408(12) . ?
C7 C8 1.404(13) . ?
C7 C6 1.370(13) . ?
C7 Br1 1.882(10) . ?
C8 C9 1.364(14) . ?
C21 C22 1.516(16) . ?
C6 C5 1.428(12) . ?
C20 C9 1.547(13) . ?
C19 C18 1.38(2) . ?
C15 C16 1.477(18) . ?

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
C14 O3 C15 117.4(8) . . ?
C17 O5 C18 117.5(9) . . ?
C14 C4 C5 125.3(8) . . ?
C3 C4 C14 114.0(8) . . ?
C3 C4 C5 120.2(7) . . ?
O3 C14 C4 112.3(8) . . ?
O4 C14 O3 124.2(8) . . ?
O4 C14 C4 123.4(9) . . ?
C5 C10 C1 117.6(7) . . ?
C9 C10 C1 123.5(7) . . ?
C9 C10 C5 118.8(7) . . ?
C20 O7 C21 113.3(8) . . ?
C11 O1 C12 117.3(7) . . ?
C10 C1 C11 120.9(7) . . ?
C2 C1 C10 121.5(8) . . ?
C2 C1 C11 117.6(8) . . ?
O5 C17 C6 109.6(9) . . ?
O6 C17 O5 125.0(9) . . ?
O6 C17 C6 125.3(9) . . ?
O1 C12 C13 112.2(9) . . ?
C4 C3 C2 120.5(8) . . ?
O2 C11 O1 124.5(8) . . ?
O2 C11 C1 122.0(8) . . ?
O1 C11 C1 113.5(8) . . ?
C8 C7 Br1 116.0(7) . . ?
C6 C7 C8 120.4(9) . . ?
C6 C7 Br1 122.5(7) . . ?
C9 C8 C7 120.8(9) . . ?
C1 C2 Br01 123.2(7) . . ?
C1 C2 C3 121.0(8) . . ?
C3 C2 Br01 115.1(7) . . ?
O7 C21 C22 105.7(9) . . ?
C7 C6 C17 116.7(8) . . ?
C7 C6 C5 119.0(8) . . ?
C5 C6 C17 123.2(8) . . ?
C10 C5 C4 119.0(7) . . ?
C10 C5 C6 119.8(6) . . ?
C6 C5 C4 121.1(7) . . ?
O7 C20 C9 109.2(8) . . ?
O8 C20 O7 128.3(10) . . ?
O8 C20 C9 122.3(9) . . ?
O3 C15 C16 105.7(10) . . ?
C10 C9 C20 123.9(8) . . ?
C8 C9 C10 121.0(8) . . ?
C8 C9 C20 115.0(8) . . ?
C19 C18 O5 113.2(13) . . ?

_olex2_submission_original_sample_id Br1EtNTE
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.311
_oxdiff_exptl_absorpt_empirical_full_min 0.845
