# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_gil10483_6m
_database_code_depnum_ccdc_archive 'CCDC 2288990'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2023-08-16 deposited with the CCDC.	2023-11-09 downloaded from the CCDC.
;

_audit_creation_method           'APEX4 v2021.4-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 F N O6 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         327.28
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_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                   6.78220(10)
_cell_length_b                   15.6869(3)
_cell_length_c                   6.85770(10)
_cell_angle_alpha                90
_cell_angle_beta                 108.4430(10)
_cell_angle_gamma                90
_cell_volume                     692.13(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9970
_cell_measurement_theta_min      2.8169
_cell_measurement_theta_max      66.6546
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.242
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.112
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336

_exptl_absorpt_coefficient_mu    2.497
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_T_max  0.77

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          'single crystal'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device       'Bruker D8 Venture Photon III'
_diffrn_measurement_device_type  'single crystal diffractometer'
_diffrn_measurement_method       'phi/omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            9796
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_theta_min         5.64
_diffrn_reflns_theta_max         66.65
_diffrn_reflns_theta_full        66.65
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8

_refine_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_number_total             2343
_reflns_number_gt                2317
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.874
_reflns_Friedel_fraction_max     0.929
_reflns_Friedel_fraction_full    0.929

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_gt          0.0670
_refine_ls_wR_factor_ref         0.0672
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_number_reflns         2343
_refine_ls_number_parameters     200
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0293P)²+0.2875P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.183
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1068 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(10)

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker APEX4 v2021.4-0 Photon III'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1242)'
_computing_publication_material  'SHELXT 2018/2 (Sheldrick, 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.2788(3) 0.27074(11) -0.0797(3) 0.0277(4) Uani d . . . 1 . .
N N1 0.2334(4) 0.68989(16) 0.6468(4) 0.0223(5) Uani d . . . 1 . .
O O1 0.5927(3) 0.38874(15) 0.6623(3) 0.0263(5) Uani d . . . 1 . .
O O2 0.8068(3) 0.41797(12) 0.3969(3) 0.0179(4) Uani d . . . 1 . .
O O3 1.0659(3) 0.52491(13) 0.4792(3) 0.0240(5) Uani d . . . 1 . .
O O4 0.8081(3) 0.52456(14) 0.1317(3) 0.0250(5) Uani d . . . 1 . .
O O5 0.2457(3) 0.68000(16) 0.8271(3) 0.0310(5) Uani d . . . 1 . .
O O6 0.0927(3) 0.72925(14) 0.5220(4) 0.0296(5) Uani d . . . 1 . .
S S1 0.85782(9) 0.51360(4) 0.34827(9) 0.01813(18) Uani d . . . 1 . .
C C1 0.5021(5) 0.37221(18) 0.4824(4) 0.0181(6) Uani d . . . 1 . .
C C2 0.6000(4) 0.38849(18) 0.3192(4) 0.0173(6) Uani d . . . 1 . .
C C3 0.5090(4) 0.37200(18) 0.1222(4) 0.0196(6) Uani d . . . 1 . .
H H3 0.584972 0.378165 0.028037 0.024000 Uiso calc U . R 1 . .
C C4 0.2859(4) 0.34354(18) 0.0459(4) 0.0214(6) Uani d . . . 1 . .
C C5 0.1986(4) 0.3176(2) 0.2116(5) 0.0225(6) Uani d . . . 1 . .
H H5 0.068462 0.289045 0.173434 0.027000 Uiso calc U . R 1 . .
C C6 0.2946(4) 0.33271(18) 0.4107(5) 0.0215(6) Uani d . . . 1 . .
H H6 0.227588 0.317648 0.508256 0.026000 Uiso calc U . R 1 . .
C C7 0.1520(5) 0.4119(2) -0.0904(5) 0.0289(7) Uani d . . . 1 . .
H H7A 0.009848 0.390444 -0.150354 0.043000 Uiso calc U . R 1 . .
H H7B 0.209213 0.426420 -0.200677 0.043000 Uiso calc U . R 1 . .
H H7C 0.150527 0.462784 -0.008070 0.043000 Uiso calc U . R 1 . .
C C11 0.6836(4) 0.57353(17) 0.4362(4) 0.0188(6) Uani d . . . 1 . .
C C12 0.7168(4) 0.57861(19) 0.6467(4) 0.0214(6) Uani d . . . 1 . .
H H12 0.838574 0.554884 0.741289 0.026000 Uiso calc U . R 1 . .
C C13 0.5706(4) 0.6185(2) 0.7161(5) 0.0216(6) Uani d . . . 1 . .
H H13 0.589241 0.622711 0.858999 0.026000 Uiso calc U . R 1 . .
C C14 0.3963(4) 0.65233(18) 0.5728(5) 0.0193(6) Uani d . . . 1 . .
C C15 0.3636(4) 0.6508(2) 0.3639(5) 0.0226(6) Uani d . . . 1 . .
H H15 0.244608 0.676930 0.270627 0.027000 Uiso calc U . R 1 . .
C C16 0.5102(5) 0.60977(19) 0.2940(5) 0.0224(6) Uani d . . . 1 . .
H H16 0.491999 0.606558 0.151013 0.027000 Uiso calc U . R 1 . .


_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C4 . 1.422(3) ?
N1 O5 . 1.223(3) ?
N1 O6 . 1.228(3) ?
N1 C14 . 1.476(4) ?
O1 C1 . 1.220(4) ?
O2 C2 . 1.411(3) ?
O2 S1 . 1.5983(19) ?
O3 S1 . 1.424(2) ?
O4 S1 . 1.426(2) ?
S1 C11 . 1.759(3) ?
C1 C6 . 1.473(4) ?
C1 C2 . 1.492(4) ?
C2 C3 . 1.322(4) ?
C3 C4 . 1.504(4) ?
C3 H3 . 0.950000 ?
C4 C5 . 1.494(4) ?
C4 C7 . 1.520(4) ?
C5 C6 . 1.334(4) ?
C5 H5 . 0.950000 ?
C6 H6 . 0.950000 ?
C7 H7A . 0.980000 ?
C7 H7B . 0.980000 ?
C7 H7C . 0.980000 ?
C11 C16 . 1.390(4) ?
C11 C12 . 1.391(4) ?
C12 C13 . 1.379(4) ?
C12 H12 . 0.950000 ?
C13 C14 . 1.382(4) ?
C13 H13 . 0.950000 ?
C14 C15 . 1.379(4) ?
C15 C16 . 1.390(4) ?
C15 H15 . 0.950000 ?
C16 H16 . 0.950000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O5 N1 O6 . . 123.9(2) ?
O5 N1 C14 . . 118.5(2) ?
O6 N1 C14 . . 117.5(2) ?
C2 O2 S1 . . 118.93(16) ?
O3 S1 O4 . . 120.16(12) ?
O3 S1 O2 . . 102.84(11) ?
O4 S1 O2 . . 109.58(12) ?
O3 S1 C11 . . 110.88(13) ?
O4 S1 C11 . . 109.26(13) ?
O2 S1 C11 . . 102.52(11) ?
O1 C1 C6 . . 123.3(3) ?
O1 C1 C2 . . 121.4(3) ?
C6 C1 C2 . . 115.3(2) ?
C3 C2 O2 . . 122.5(3) ?
C3 C2 C1 . . 123.9(3) ?
O2 C2 C1 . . 113.4(2) ?
C2 C3 C4 . . 120.5(3) ?
C2 C3 H3 . . 119.800000 ?
C4 C3 H3 . . 119.800000 ?
F1 C4 C5 . . 107.3(2) ?
F1 C4 C3 . . 106.7(2) ?
C5 C4 C3 . . 114.4(2) ?
F1 C4 C7 . . 107.1(2) ?
C5 C4 C7 . . 110.9(2) ?
C3 C4 C7 . . 110.1(2) ?
C6 C5 C4 . . 123.2(3) ?
C6 C5 H5 . . 118.400000 ?
C4 C5 H5 . . 118.400000 ?
C5 C6 C1 . . 121.4(3) ?
C5 C6 H6 . . 119.300000 ?
C1 C6 H6 . . 119.300000 ?
C4 C7 H7A . . 109.500000 ?
C4 C7 H7B . . 109.500000 ?
H7A C7 H7B . . 109.500000 ?
C4 C7 H7C . . 109.500000 ?
H7A C7 H7C . . 109.500000 ?
H7B C7 H7C . . 109.500000 ?
C16 C11 C12 . . 121.9(3) ?
C16 C11 S1 . . 119.3(2) ?
C12 C11 S1 . . 118.7(2) ?
C13 C12 C11 . . 119.1(3) ?
C13 C12 H12 . . 120.500000 ?
C11 C12 H12 . . 120.500000 ?
C12 C13 C14 . . 118.4(3) ?
C12 C13 H13 . . 120.800000 ?
C14 C13 H13 . . 120.800000 ?
C15 C14 C13 . . 123.5(3) ?
C15 C14 N1 . . 118.2(2) ?
C13 C14 N1 . . 118.3(3) ?
C14 C15 C16 . . 118.0(3) ?
C14 C15 H15 . . 121.000000 ?
C16 C15 H15 . . 121.000000 ?
C11 C16 C15 . . 119.1(3) ?
C11 C16 H16 . . 120.500000 ?
C15 C16 H16 . . 120.500000 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 O2 S1 O3 . . . . 169.7(2) ?
C2 O2 S1 O4 . . . . -61.4(2) ?
C2 O2 S1 C11 . . . . 54.6(2) ?
S1 O2 C2 C3 . . . . 72.1(3) ?
S1 O2 C2 C1 . . . . -112.1(2) ?
O1 C1 C2 C3 . . . . -179.9(3) ?
C6 C1 C2 C3 . . . . 2.1(4) ?
O1 C1 C2 O2 . . . . 4.3(4) ?
C6 C1 C2 O2 . . . . -173.7(2) ?
O2 C2 C3 C4 . . . . -177.9(2) ?
C1 C2 C3 C4 . . . . 6.6(4) ?
C2 C3 C4 F1 . . . . -131.5(3) ?
C2 C3 C4 C5 . . . . -13.0(4) ?
C2 C3 C4 C7 . . . . 112.6(3) ?
F1 C4 C5 C6 . . . . 129.8(3) ?
C3 C4 C5 C6 . . . . 11.7(4) ?
C7 C4 C5 C6 . . . . -113.5(3) ?
C4 C5 C6 C1 . . . . -3.6(5) ?
O1 C1 C6 C5 . . . . 178.3(3) ?
C2 C1 C6 C5 . . . . -3.7(4) ?
O3 S1 C11 C16 . . . . 144.9(2) ?
O4 S1 C11 C16 . . . . 10.3(3) ?
O2 S1 C11 C16 . . . . -105.9(2) ?
O3 S1 C11 C12 . . . . -39.1(3) ?
O4 S1 C11 C12 . . . . -173.8(2) ?
O2 S1 C11 C12 . . . . 70.0(2) ?
C16 C11 C12 C13 . . . . 1.9(4) ?
S1 C11 C12 C13 . . . . -173.9(2) ?
C11 C12 C13 C14 . . . . -0.2(4) ?
C12 C13 C14 C15 . . . . -2.2(4) ?
C12 C13 C14 N1 . . . . 176.0(3) ?
O5 N1 C14 C15 . . . . 169.0(3) ?
O6 N1 C14 C15 . . . . -10.9(4) ?
O5 N1 C14 C13 . . . . -9.3(4) ?
O6 N1 C14 C13 . . . . 170.9(3) ?
C13 C14 C15 C16 . . . . 2.8(4) ?
N1 C14 C15 C16 . . . . -175.3(2) ?
C12 C11 C16 C15 . . . . -1.3(4) ?
S1 C11 C16 C15 . . . . 174.5(2) ?
C14 C15 C16 C11 . . . . -1.0(4) ?

####################################################################### 
# 
# 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_gil10471_28
_database_code_depnum_ccdc_archive 'CCDC 2288992'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2023-08-16 deposited with the CCDC.	2023-11-09 downloaded from the CCDC.
;

_audit_creation_method           'APEX4 v2022.10-1'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 Br F O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         237.03
_chemical_absolute_configuration .

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.4447(2)
_cell_length_b                   9.8276(3)
_cell_length_c                   12.3314(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     781.02(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      5.7570
_cell_measurement_theta_max      66.5708
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.111
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.047
_exptl_crystal_density_diffrn    2.016
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464

_exptl_absorpt_coefficient_mu    7.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_T_max  0.73

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device       'Bruker D8 Venture Photon III'
_diffrn_measurement_device_type  'single crystal diffractometer'
_diffrn_measurement_method       'phi/omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            12498
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_theta_min         5.76
_diffrn_reflns_theta_max         66.60
_diffrn_reflns_theta_full        66.60
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;

Refined as a 2-component inversion twin.
;

_reflns_number_total             1359
_reflns_number_gt                1356
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.670
_reflns_Friedel_fraction_max     0.984
_reflns_Friedel_fraction_full    0.984

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0139
_refine_ls_R_factor_gt           0.0138
_refine_ls_wR_factor_gt          0.0351
_refine_ls_wR_factor_ref         0.0352
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_number_reflns         1359
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0176P)²+0.3057P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.238
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.19(2)

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'
F F 0.0727 0.0534 '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'

_computing_data_collection       'Bruker APEX4 v2022.10-1 Photon III'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1380)'
_computing_publication_material  'SHELXT 2011/1 (Sheldrick, 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.98904(4) 0.56508(2) 0.34999(2) 0.01651(10) Uani d . . . 1 . .
F F1 0.5311(2) 0.16778(12) 0.19827(11) 0.0177(3) Uani d . . . 1 . .
O O1 0.6342(3) 0.53789(18) 0.51294(14) 0.0193(4) Uani d . . . 1 . .
O O2 0.4768(3) 0.21090(15) 0.43220(12) 0.0159(3) Uani d . . . 1 . .
O O3 0.8453(2) 0.29423(17) 0.33726(13) 0.0134(3) Uani d . . . 1 . .
C C1 0.6202(4) 0.4482(3) 0.44662(19) 0.0142(5) Uani d . . . 1 . .
C C2 0.4359(4) 0.3552(2) 0.4453(2) 0.0144(5) Uani d . . . 1 . .
H H2 0.319103 0.379814 0.494920 0.017000 Uiso calc U . R 1 . .
C C3 0.3784(4) 0.2821(2) 0.3450(2) 0.0147(5) Uani d . . . 1 . .
H H3 0.226877 0.263556 0.335488 0.018000 Uiso calc U . R 1 . .
C C4 0.5002(6) 0.3008(2) 0.24162(17) 0.0140(4) Uani d . . . 1 . .
C C5 0.7156(4) 0.3588(2) 0.25617(19) 0.0135(5) Uani d . . . 1 . .
H H5 0.787549 0.389053 0.188476 0.016000 Uiso calc U . R 1 . .
C C6 0.7770(3) 0.4291(2) 0.35676(18) 0.0129(4) Uani d . . . 1 . .
C C7 0.3809(4) 0.3830(2) 0.1592(2) 0.0167(5) Uani d . . . 1 . .
H H7A 0.246428 0.339767 0.145559 0.025000 Uiso calc U . R 1 . .
H H7B 0.460043 0.387426 0.091375 0.025000 Uiso calc U . R 1 . .
H H7C 0.358922 0.475308 0.186998 0.025000 Uiso calc U . R 1 . .


_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C6 . 1.913(2) ?
F1 C4 . 1.426(2) ?
O1 C1 . 1.206(3) ?
O2 C3 . 1.431(3) ?
O2 C2 . 1.451(3) ?
O3 C6 . 1.417(3) ?
O3 C5 . 1.450(3) ?
C1 C2 . 1.499(4) ?
C1 C6 . 1.512(3) ?
C2 C3 . 1.477(4) ?
C2 H2 . 1.000000 ?
C3 C4 . 1.508(4) ?
C3 H3 . 1.000000 ?
C4 C7 . 1.509(3) ?
C4 C5 . 1.512(4) ?
C5 C6 . 1.474(3) ?
C5 H5 . 1.000000 ?
C7 H7A . 0.980000 ?
C7 H7B . 0.980000 ?
C7 H7C . 0.980000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 O2 C2 . . 61.65(15) ?
C6 O3 C5 . . 61.87(14) ?
O1 C1 C2 . . 120.9(2) ?
O1 C1 C6 . . 122.5(2) ?
C2 C1 C6 . . 116.5(2) ?
O2 C2 C3 . . 58.52(14) ?
O2 C2 C1 . . 117.0(2) ?
C3 C2 C1 . . 120.3(2) ?
O2 C2 H2 . . 116.200000 ?
C3 C2 H2 . . 116.200000 ?
C1 C2 H2 . . 116.200000 ?
O2 C3 C2 . . 59.82(15) ?
O2 C3 C4 . . 117.6(2) ?
C2 C3 C4 . . 121.2(2) ?
O2 C3 H3 . . 115.600000 ?
C2 C3 H3 . . 115.600000 ?
C4 C3 H3 . . 115.600000 ?
F1 C4 C3 . . 106.14(18) ?
F1 C4 C7 . . 108.02(19) ?
C3 C4 C7 . . 111.7(2) ?
F1 C4 C5 . . 105.2(2) ?
C3 C4 C5 . . 115.07(19) ?
C7 C4 C5 . . 110.21(19) ?
O3 C5 C6 . . 57.99(14) ?
O3 C5 C4 . . 116.50(19) ?
C6 C5 C4 . . 121.6(2) ?
O3 C5 H5 . . 116.000000 ?
C6 C5 H5 . . 116.000000 ?
C4 C5 H5 . . 116.000000 ?
O3 C6 C5 . . 60.14(15) ?
O3 C6 C1 . . 116.63(18) ?
C5 C6 C1 . . 119.7(2) ?
O3 C6 Br1 . . 115.10(14) ?
C5 C6 Br1 . . 118.84(16) ?
C1 C6 Br1 . . 115.01(17) ?
C4 C7 H7A . . 109.500000 ?
C4 C7 H7B . . 109.500000 ?
H7A C7 H7B . . 109.500000 ?
C4 C7 H7C . . 109.500000 ?
H7A C7 H7C . . 109.500000 ?
H7B C7 H7C . . 109.500000 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 O2 C2 C1 . . . . -110.6(2) ?
O1 C1 C2 O2 . . . . -135.2(2) ?
C6 C1 C2 O2 . . . . 48.7(3) ?
O1 C1 C2 C3 . . . . 157.2(2) ?
C6 C1 C2 C3 . . . . -18.9(3) ?
C2 O2 C3 C4 . . . . 111.8(2) ?
C1 C2 C3 O2 . . . . 104.9(2) ?
O2 C2 C3 C4 . . . . -106.0(2) ?
C1 C2 C3 C4 . . . . -1.0(3) ?
O2 C3 C4 F1 . . . . 65.2(3) ?
C2 C3 C4 F1 . . . . 134.9(2) ?
O2 C3 C4 C7 . . . . -177.3(2) ?
C2 C3 C4 C7 . . . . -107.6(3) ?
O2 C3 C4 C5 . . . . -50.7(3) ?
C2 C3 C4 C5 . . . . 19.0(3) ?
C6 O3 C5 C4 . . . . -112.2(2) ?
F1 C4 C5 O3 . . . . -66.8(2) ?
C3 C4 C5 O3 . . . . 49.6(3) ?
C7 C4 C5 O3 . . . . 176.98(19) ?
F1 C4 C5 C6 . . . . -133.9(2) ?
C3 C4 C5 C6 . . . . -17.5(3) ?
C7 C4 C5 C6 . . . . 109.9(2) ?
C5 O3 C6 C1 . . . . 110.6(2) ?
C5 O3 C6 Br1 . . . . -110.21(19) ?
C4 C5 C6 O3 . . . . 103.5(2) ?
O3 C5 C6 C1 . . . . -105.5(2) ?
C4 C5 C6 C1 . . . . -2.0(3) ?
O3 C5 C6 Br1 . . . . 104.01(18) ?
C4 C5 C6 Br1 . . . . -152.48(17) ?
O1 C1 C6 O3 . . . . 135.2(2) ?
C2 C1 C6 O3 . . . . -48.9(3) ?
O1 C1 C6 C5 . . . . -155.6(2) ?
C2 C1 C6 C5 . . . . 20.3(3) ?
O1 C1 C6 Br1 . . . . -4.1(3) ?
C2 C1 C6 Br1 . . . . 171.88(16) ?

####################################################################### 
# 
# 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_gil10452_30
_database_code_depnum_ccdc_archive 'CCDC 2288993'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2023-08-16 deposited with the CCDC.	2023-11-09 downloaded from the CCDC.
;

_audit_creation_method           'APEX4 v2021.4-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H10 Br F O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         237.07

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   8.6997(4)
_cell_length_b                   15.8634(8)
_cell_length_c                   6.6702(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.677(2)
_cell_angle_gamma                90
_cell_volume                     898.09(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8485
_cell_measurement_theta_min      5.2113
_cell_measurement_theta_max      66.5201
_cell_measurement_temperature    101.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.342
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.064
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472

_exptl_absorpt_coefficient_mu    6.071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.49
_exptl_absorpt_correction_T_max  0.70

_exptl_special_details           
;
;

_diffrn_ambient_temperature      101.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device       'Bruker D8 Venture Photon III'
_diffrn_measurement_device_type  'single crystal diffractometer'
_diffrn_measurement_method       'phi/omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            12842
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_theta_min         5.58
_diffrn_reflns_theta_max         66.91
_diffrn_reflns_theta_full        66.91
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7

_refine_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_number_total             1569
_reflns_number_gt                1421
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_gt          0.0694
_refine_ls_wR_factor_ref         0.0714
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_number_reflns         1569
_refine_ls_number_parameters     111
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0131P)²+2.3775P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.373
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
F F 0.0727 0.0534 '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'

_computing_data_collection       'Bruker APEX4 v2021.4-0 Photon III'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1242)'
_computing_publication_material  'SHELXT 2018/2 (Sheldrick, 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.42540(4) 0.66949(2) 0.57491(6) 0.03324(14) Uani d . . . 1 . .
C C1 0.2812(4) 0.50787(19) 0.6016(5) 0.0226(7) Uani d . . . 1 . .
C C2 0.3964(4) 0.5691(2) 0.7329(5) 0.0250(7) Uani d . . . 1 . .
H H2 0.500544 0.540210 0.776367 0.030000 Uiso calc U . R 1 . .
C C3 0.3341(4) 0.58628(19) 0.9205(5) 0.0239(7) Uani d . . . 1 . .
H H3 0.408331 0.604071 1.050186 0.029000 Uiso calc U . R 1 . .
C C4 0.2092(3) 0.51725(19) 0.9292(5) 0.0212(6) Uani d . . . 1 . .
H H4 0.204620 0.491426 1.064492 0.025000 Uiso calc U . R 1 . .
C C5 0.1927(4) 0.46148(18) 0.7425(4) 0.0213(6) Uani d . . . 1 . .
H H5 0.079796 0.451778 0.674321 0.026000 Uiso calc U . R 1 . .
C C6 0.1628(4) 0.6073(2) 0.8895(5) 0.0231(7) Uani d . . . 1 . .
C C7 0.0993(4) 0.6590(2) 1.0395(5) 0.0281(7) Uani d . . . 1 . .
H H7A 0.152499 0.643247 1.179654 0.042000 Uiso calc U . R 1 . .
H H7B -0.014083 0.648927 1.020400 0.042000 Uiso calc U . R 1 . .
H H7C 0.117908 0.718876 1.017195 0.042000 Uiso calc U . R 1 . .
C C8 0.2244(4) 0.3176(2) 0.6619(5) 0.0276(7) Uani d . . . 1 . .
H H8A 0.112942 0.304787 0.653289 0.041000 Uiso calc U . R 1 . .
H H8B 0.287937 0.267257 0.706801 0.041000 Uiso calc U . R 1 . .
H H8C 0.239199 0.335103 0.526475 0.041000 Uiso calc U . R 1 . .
F F1 0.08636(19) 0.62537(11) 0.6874(3) 0.0255(4) Uani d . . . 1 . .
O O1 0.2664(3) 0.49556(15) 0.4200(3) 0.0330(5) Uani d . . . 1 . .
O O2 0.2729(2) 0.38440(13) 0.8068(3) 0.0231(5) Uani d . . . 1 . .


_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C2 . 1.956(3) ?
C1 O1 . 1.205(4) ?
C1 C2 . 1.527(4) ?
C1 C5 . 1.528(4) ?
C2 C3 . 1.494(5) ?
C2 H2 . 1.000000 ?
C3 C6 . 1.497(4) ?
C3 C4 . 1.552(4) ?
C3 H3 . 1.000000 ?
C4 C6 . 1.493(4) ?
C4 C5 . 1.508(4) ?
C4 H4 . 1.000000 ?
C5 O2 . 1.426(3) ?
C5 H5 . 1.000000 ?
C6 F1 . 1.395(3) ?
C6 C7 . 1.490(5) ?
C7 H7A . 0.980000 ?
C7 H7B . 0.980000 ?
C7 H7C . 0.980000 ?
C8 O2 . 1.434(4) ?
C8 H8A . 0.980000 ?
C8 H8B . 0.980000 ?
C8 H8C . 0.980000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 C2 . . 126.3(3) ?
O1 C1 C5 . . 125.7(3) ?
C2 C1 C5 . . 108.0(2) ?
C3 C2 C1 . . 106.5(3) ?
C3 C2 Br1 . . 114.6(2) ?
C1 C2 Br1 . . 110.8(2) ?
C3 C2 H2 . . 108.300000 ?
C1 C2 H2 . . 108.300000 ?
Br1 C2 H2 . . 108.300000 ?
C2 C3 C6 . . 117.3(3) ?
C2 C3 C4 . . 106.7(3) ?
C6 C3 C4 . . 58.6(2) ?
C2 C3 H3 . . 119.400000 ?
C6 C3 H3 . . 119.400000 ?
C4 C3 H3 . . 119.400000 ?
C6 C4 C5 . . 116.2(3) ?
C6 C4 C3 . . 58.8(2) ?
C5 C4 C3 . . 108.9(3) ?
C6 C4 H4 . . 119.300000 ?
C5 C4 H4 . . 119.300000 ?
C3 C4 H4 . . 119.300000 ?
O2 C5 C4 . . 107.6(2) ?
O2 C5 C1 . . 108.6(2) ?
C4 C5 C1 . . 104.8(2) ?
O2 C5 H5 . . 111.800000 ?
C4 C5 H5 . . 111.800000 ?
C1 C5 H5 . . 111.800000 ?
F1 C6 C7 . . 111.6(3) ?
F1 C6 C4 . . 114.9(3) ?
C7 C6 C4 . . 122.2(3) ?
F1 C6 C3 . . 115.3(3) ?
C7 C6 C3 . . 122.3(3) ?
C4 C6 C3 . . 62.6(2) ?
C6 C7 H7A . . 109.500000 ?
C6 C7 H7B . . 109.500000 ?
H7A C7 H7B . . 109.500000 ?
C6 C7 H7C . . 109.500000 ?
H7A C7 H7C . . 109.500000 ?
H7B C7 H7C . . 109.500000 ?
O2 C8 H8A . . 109.500000 ?
O2 C8 H8B . . 109.500000 ?
H8A C8 H8B . . 109.500000 ?
O2 C8 H8C . . 109.500000 ?
H8A C8 H8C . . 109.500000 ?
H8B C8 H8C . . 109.500000 ?
C5 O2 C8 . . 112.3(2) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . 159.7(3) ?
C5 C1 C2 C3 . . . . -23.0(3) ?
O1 C1 C2 Br1 . . . . 34.4(4) ?
C5 C1 C2 Br1 . . . . -148.2(2) ?
C1 C2 C3 C6 . . . . -47.5(3) ?
Br1 C2 C3 C6 . . . . 75.3(3) ?
C1 C2 C3 C4 . . . . 15.3(3) ?
Br1 C2 C3 C4 . . . . 138.1(2) ?
C2 C3 C4 C6 . . . . -112.2(3) ?
C2 C3 C4 C5 . . . . -2.3(3) ?
C6 C3 C4 C5 . . . . 109.8(3) ?
C6 C4 C5 O2 . . . . 167.8(2) ?
C3 C4 C5 O2 . . . . 104.0(3) ?
C6 C4 C5 C1 . . . . 52.3(3) ?
C3 C4 C5 C1 . . . . -11.5(3) ?
O1 C1 C5 O2 . . . . 83.6(4) ?
C2 C1 C5 O2 . . . . -93.7(3) ?
O1 C1 C5 C4 . . . . -161.5(3) ?
C2 C1 C5 C4 . . . . 21.1(3) ?
C5 C4 C6 F1 . . . . 9.8(4) ?
C3 C4 C6 F1 . . . . 106.9(3) ?
C5 C4 C6 C7 . . . . 150.3(3) ?
C3 C4 C6 C7 . . . . -112.6(3) ?
C5 C4 C6 C3 . . . . -97.1(3) ?
C2 C3 C6 F1 . . . . -12.4(4) ?
C4 C3 C6 F1 . . . . -106.2(3) ?
C2 C3 C6 C7 . . . . -153.8(3) ?
C4 C3 C6 C7 . . . . 112.5(3) ?
C2 C3 C6 C4 . . . . 93.7(3) ?
C4 C5 O2 C8 . . . . 161.4(2) ?
C1 C5 O2 C8 . . . . -85.6(3) ?

####################################################################### 
# 
# 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_gil10466_23
_database_code_depnum_ccdc_archive 'CCDC 2288991'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2023-08-16 deposited with the CCDC.	2023-11-09 downloaded from the CCDC.
;

_audit_creation_method           'APEX4 v2021.4-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H33 I N2 O10'
_chemical_formula_iupac          ?
_chemical_formula_weight         660.44
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.00380(10)
_cell_length_b                   15.9234(2)
_cell_length_c                   28.8087(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3212.87(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9826
_cell_measurement_theta_min      3.1711
_cell_measurement_theta_max      66.6542
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.144
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.065
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344

_exptl_absorpt_coefficient_mu    8.272
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.49
_exptl_absorpt_correction_T_max  0.61

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          'single crystal'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device       'Bruker D8 Venture Photon III'
_diffrn_measurement_device_type  'single crystal diffractometer'
_diffrn_measurement_method       'phi/omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            28879
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         66.78
_diffrn_reflns_theta_full        66.78
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34

_refine_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.

A badly disordered half heptane molecule was found in the 
asymmetrical unit and could not be satisfactorily refined. The program 
SQUEEZE (Spek, A.L. (2015). Acta Cryst. C71, 9-18.) was therefore used to
remove mathematically the effect of the solvent.
The quoted formula and derived parameters are not included the squeezed
solvent molecule.
;

_reflns_number_total             5552
_reflns_number_gt                5308
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_max     0.943
_reflns_Friedel_fraction_full    0.944

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_gt          0.0710
_refine_ls_wR_factor_ref         0.0721
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.055
_refine_ls_number_reflns         5552
_refine_ls_number_parameters     500
_refine_ls_number_restraints     489
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0390P)²+0.8051P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.593
_refine_diff_density_min         -0.298
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 2109 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.056(3)

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'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'

_computing_data_collection       'Bruker APEX4 v2021.4-0 Photon III'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1242)'
_computing_publication_material  'SHELXT 2018/2 (Sheldrick, 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I1 0.31878(4) 0.44200(2) 0.48287(2) 0.02624(10) Uani d . . . 1.000000 . .
N N2 0.1286(6) 0.1777(3) 0.39517(13) 0.0250(9) Uani d U . . 1.000000 . .
O O5 0.7024(7) 0.5959(2) 0.24564(14) 0.0431(10) Uani d U . . 1.000000 . .
O O6 0.6226(5) 0.7312(2) 0.23717(12) 0.0310(8) Uani d U . . 1.000000 . .
O O7 0.0488(5) 0.3534(2) 0.41285(11) 0.0280(8) Uani d U . . 1.000000 . .
O O8 -0.0837(6) 0.1875(2) 0.33694(12) 0.0346(9) Uani d U . . 1.000000 . .
C C1 0.3287(8) 0.4330(3) 0.41003(15) 0.0286(10) Uani d U . D 1.000000 . .
C C6 0.1899(9) 0.3873(3) 0.38622(15) 0.0287(11) Uani d U . D 1.000000 . .
N N1 0.8805(6) 0.6369(3) 0.32997(15) 0.0291(10) Uani d U . D 1.000000 . .
C C2 0.486(2) 0.4714(15) 0.3897(5) 0.025(3) Uani d U P D 0.634(16) A 1
C C3 0.514(2) 0.4613(10) 0.3418(4) 0.027(3) Uani d U P D 0.634(16) A 1
H H3 0.620784 0.485162 0.326399 0.033000 Uiso calc U P R 0.634(16) A 1
C C4 0.3783(19) 0.4150(7) 0.3177(3) 0.024(3) Uani d U P D 0.634(16) A 1
C C5 0.220(2) 0.3769(9) 0.3385(3) 0.026(3) Uani d U P D 0.634(16) A 1
H H5 0.134269 0.344192 0.320487 0.031000 Uiso calc U P R 0.634(16) A 1
C C7 0.395(2) 0.4094(6) 0.2663(3) 0.030(3) Uani d U P D 0.634(16) A 1
O O1 0.2640(19) 0.4076(7) 0.2400(3) 0.039(3) Uani d U P D 0.634(16) A 1
O O2 0.5771(14) 0.4057(4) 0.2534(3) 0.035(2) Uani d U P D 0.634(16) A 1
C C8 0.615(2) 0.4096(6) 0.2039(4) 0.049(3) Uani d U P D 0.634(16) A 1
H H8A 0.538123 0.367102 0.187839 0.073000 Uiso calc U P R 0.634(16) A 1
H H8B 0.750635 0.398930 0.198190 0.073000 Uiso calc U P R 0.634(16) A 1
H H8C 0.581225 0.465487 0.192175 0.073000 Uiso calc U P R 0.634(16) A 1
O O3 0.6021(18) 0.5206(10) 0.4158(4) 0.029(3) Uani d U P D 0.634(16) A 1
C C11 0.7777(19) 0.5541(9) 0.3980(5) 0.026(3) Uani d U P D 0.634(16) A 1
H H11 0.854840 0.507836 0.383872 0.032000 Uiso calc U P R 0.634(16) A 1
C C12 0.883(2) 0.5905(11) 0.4386(5) 0.043(3) Uani d U P D 0.634(16) A 1
H H12A 0.811075 0.637833 0.451288 0.064000 Uiso calc U P R 0.634(16) A 1
H H12B 1.009364 0.609951 0.428387 0.064000 Uiso calc U P R 0.634(16) A 1
H H12C 0.898882 0.547302 0.462524 0.064000 Uiso calc U P R 0.634(16) A 1
C C13 0.7395(19) 0.6225(11) 0.3611(5) 0.022(4) Uani d U P D 0.634(16) A 1
O O4 0.583(4) 0.657(3) 0.3574(17) 0.034(5) Uani d U P D 0.634(16) A 1
C C2A 0.462(4) 0.471(3) 0.3810(6) 0.024(7) Uani d U P D 0.366(16) A 2
C C3A 0.461(3) 0.4602(17) 0.3332(6) 0.022(5) Uani d U P D 0.366(16) A 2
H H3A 0.563699 0.481151 0.315142 0.026000 Uiso calc U P R 0.366(16) A 2
C C4A 0.310(3) 0.4194(15) 0.3112(5) 0.029(5) Uani d U P D 0.366(16) A 2
C C5A 0.164(3) 0.3847(17) 0.3380(5) 0.029(6) Uani d U P D 0.366(16) A 2
H H5A 0.053018 0.360727 0.324390 0.035000 Uiso calc U P R 0.366(16) A 2
C C7A 0.302(4) 0.4174(13) 0.2601(6) 0.030(5) Uani d U P D 0.366(16) A 2
O O1A 0.164(3) 0.4014(9) 0.2375(5) 0.031(4) Uani d U P D 0.366(16) A 2
O O2A 0.475(2) 0.4322(11) 0.2411(4) 0.044(4) Uani d U P D 0.366(16) A 2
C C8A 0.483(4) 0.4323(16) 0.1902(5) 0.057(6) Uani d U P D 0.366(16) A 2
H H8A1 0.458123 0.375544 0.178588 0.085000 Uiso calc U P R 0.366(16) A 2
H H8A2 0.610382 0.450431 0.180102 0.085000 Uiso calc U P R 0.366(16) A 2
H H8A3 0.386917 0.471034 0.177938 0.085000 Uiso calc U P R 0.366(16) A 2
O O3A 0.599(4) 0.5066(19) 0.4072(8) 0.036(6) Uani d U P D 0.366(16) A 2
C C11A 0.774(3) 0.5343(12) 0.3872(7) 0.015(5) Uani d U P D 0.366(16) A 2
H H11A 0.836127 0.487286 0.369949 0.019000 Uiso calc U P R 0.366(16) A 2
C C12A 0.895(3) 0.5606(14) 0.4274(7) 0.028(5) Uani d U P D 0.366(16) A 2
H H12D 0.829113 0.604822 0.444857 0.043000 Uiso calc U P R 0.366(16) A 2
H H12E 1.017088 0.582022 0.415898 0.043000 Uiso calc U P R 0.366(16) A 2
H H12F 0.917274 0.512241 0.447669 0.043000 Uiso calc U P R 0.366(16) A 2
C C13A 0.731(3) 0.6082(16) 0.3539(9) 0.015(6) Uani d U P D 0.366(16) A 2
O O4A 0.579(6) 0.647(5) 0.355(3) 0.034(5) Uani d U P D 0.366(16) A 2
C C14 0.8519(7) 0.7010(3) 0.29377(16) 0.0234(10) Uani d U . . 1.000000 . .
H H14 0.799328 0.753644 0.307767 0.028000 Uiso calc U . R 1.000000 . .
C C15 1.0534(8) 0.7163(3) 0.27560(18) 0.0317(12) Uani d U . . 1.000000 . .
H H15A 1.119305 0.760080 0.293986 0.038000 Uiso calc U . R 1.000000 . .
H H15B 1.051317 0.733421 0.242576 0.038000 Uiso calc U . R 1.000000 . .
C C16 1.1498(8) 0.6311(4) 0.2816(2) 0.0399(14) Uani d U . . 1.000000 . .
H H16A 1.116242 0.592749 0.255761 0.048000 Uiso calc U . R 1.000000 . .
H H16B 1.290420 0.637100 0.282900 0.048000 Uiso calc U . R 1.000000 . .
C C17 1.0718(9) 0.5989(5) 0.3272(2) 0.0485(16) Uani d U . . 1.000000 . .
H H17A 1.063846 0.536851 0.327249 0.058000 Uiso calc U . R 1.000000 . .
H H17B 1.152689 0.617247 0.353515 0.058000 Uiso calc U . R 1.000000 . .
C C18 0.7175(7) 0.6680(3) 0.25669(16) 0.0257(10) Uani d U . . 1.000000 . .
C C19 0.4946(8) 0.7095(4) 0.19935(19) 0.0374(13) Uani d U . . 1.000000 . .
H H19A 0.564423 0.711473 0.169898 0.056000 Uiso calc U . R 1.000000 . .
H H19B 0.388508 0.749566 0.198420 0.056000 Uiso calc U . R 1.000000 . .
H H19C 0.444400 0.652685 0.204228 0.056000 Uiso calc U . R 1.000000 . .
C C21 -0.0895(8) 0.3002(3) 0.39037(17) 0.0292(11) Uani d U . . 1.000000 . .
H H21 -0.145323 0.331859 0.363618 0.035000 Uiso calc U . R 1.000000 . .
C C22 -0.2467(8) 0.2839(4) 0.4252(2) 0.0334(12) Uani d U . . 1.000000 . .
H H22A -0.194262 0.253556 0.451907 0.050000 Uiso calc U . R 1.000000 . .
H H22B -0.347060 0.250029 0.410650 0.050000 Uiso calc U . R 1.000000 . .
H H22C -0.300579 0.337475 0.435590 0.050000 Uiso calc U . R 1.000000 . .
C C23 -0.0103(7) 0.2177(3) 0.37226(16) 0.0257(11) Uani d U . . 1.000000 . .
C C24 0.1799(9) 0.0931(3) 0.37978(16) 0.0298(10) Uani d U . . 1.000000 . .
H H24 0.212346 0.093007 0.345979 0.036000 Uiso calc U . R 1.000000 . .
C C25 0.3567(8) 0.0720(4) 0.4091(2) 0.0379(13) Uani d U . . 1.000000 . .
H H25A 0.368344 0.010681 0.414042 0.045000 Uiso calc U . R 1.000000 . .
H H25B 0.474761 0.093041 0.394200 0.045000 Uiso calc U . R 1.000000 . .
C C26 0.3174(9) 0.1178(3) 0.45470(17) 0.0324(11) Uani d U . . 1.000000 . .
H H26A 0.437887 0.129829 0.471393 0.039000 Uiso calc U . R 1.000000 . .
H H26B 0.233352 0.083972 0.475048 0.039000 Uiso calc U . R 1.000000 . .
C C27 0.2185(7) 0.1993(3) 0.43984(16) 0.0268(11) Uani d U . . 1.000000 . .
H H27A 0.121394 0.216534 0.462928 0.032000 Uiso calc U . R 1.000000 . .
H H27B 0.312224 0.245287 0.435999 0.032000 Uiso calc U . R 1.000000 . .
C C28 0.0150(10) 0.0332(4) 0.38957(19) 0.0390(15) Uani d U . D 1.000000 . .
O O9 -0.123(4) 0.0580(17) 0.4110(12) 0.031(5) Uani d U P D 0.47(2) B 1
O O10 0.003(2) -0.0300(8) 0.3614(4) 0.043(3) Uani d U P D 0.47(2) B 1
C C29 -0.157(3) -0.0854(10) 0.3690(6) 0.054(5) Uani d U P D 0.47(2) B 1
H H29A -0.144324 -0.112226 0.399489 0.080000 Uiso calc U P R 0.47(2) B 1
H H29B -0.158893 -0.128665 0.344801 0.080000 Uiso calc U P R 0.47(2) B 1
H H29C -0.275869 -0.053141 0.367921 0.080000 Uiso calc U P R 0.47(2) B 1
O O9A -0.120(4) 0.0376(16) 0.4148(11) 0.037(5) Uani d U P D 0.53(2) B 2
O O10A 0.081(2) -0.0481(7) 0.3760(5) 0.050(3) Uani d U P D 0.53(2) B 2
C C29A -0.046(4) -0.1181(11) 0.3844(7) 0.079(7) Uani d U P D 0.53(2) B 2
H H29D 0.029201 -0.166920 0.394294 0.118000 Uiso calc U P R 0.53(2) B 2
H H29E -0.114593 -0.131731 0.355753 0.118000 Uiso calc U P R 0.53(2) B 2
H H29F -0.137175 -0.103176 0.408730 0.118000 Uiso calc U P R 0.53(2) B 2


_geom_special_details            
;

All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I1 C1 . 2.104(4) ?
N2 C23 . 1.337(7) ?
N2 C24 . 1.464(6) ?
N2 C27 . 1.473(6) ?
O5 C18 . 1.197(6) ?
O6 C18 . 1.330(6) ?
O6 C19 . 1.453(6) ?
O7 C6 . 1.363(7) ?
O7 C21 . 1.440(7) ?
O8 C23 . 1.237(6) ?
C1 C2 . 1.393(11) ?
C1 C2A . 1.394(16) ?
C1 C6 . 1.394(8) ?
C6 C5A . 1.400(15) ?
C6 C5 . 1.401(10) ?
N1 C13A . 1.335(17) ?
N1 C13 . 1.353(12) ?
N1 C17 . 1.472(8) ?
N1 C14 . 1.474(6) ?
C2 O3 . 1.355(15) ?
C2 C3 . 1.403(14) ?
C3 C4 . 1.387(14) ?
C3 H3 . 0.950000 ?
C4 C5 . 1.398(13) ?
C4 C7 . 1.486(12) ?
C5 H5 . 0.950000 ?
C7 O1 . 1.187(16) ?
C7 O2 . 1.333(15) ?
O2 C8 . 1.453(11) ?
C8 H8A . 0.980000 ?
C8 H8B . 0.980000 ?
C8 H8C . 0.980000 ?
O3 C11 . 1.436(11) ?
C11 C12 . 1.500(16) ?
C11 C13 . 1.545(12) ?
C11 H11 . 1.000000 ?
C12 H12A . 0.980000 ?
C12 H12B . 0.980000 ?
C12 H12C . 0.980000 ?
C13 O4 . 1.227(13) ?
C2A O3A . 1.35(2) ?
C2A C3A . 1.388(16) ?
C3A C4A . 1.389(16) ?
C3A H3A . 0.950000 ?
C4A C5A . 1.399(17) ?
C4A C7A . 1.474(18) ?
C5A H5A . 0.950000 ?
C7A O1A . 1.19(2) ?
C7A O2A . 1.35(2) ?
O2A C8A . 1.466(16) ?
C8A H8A1 . 0.980000 ?
C8A H8A2 . 0.980000 ?
C8A H8A3 . 0.980000 ?
O3A C11A . 1.420(18) ?
C11A C12A . 1.49(2) ?
C11A C13A . 1.547(17) ?
C11A H11A . 1.000000 ?
C12A H12D . 0.980000 ?
C12A H12E . 0.980000 ?
C12A H12F . 0.980000 ?
C13A O4A . 1.227(19) ?
C14 C18 . 1.517(7) ?
C14 C15 . 1.525(7) ?
C14 H14 . 1.000000 ?
C15 C16 . 1.525(8) ?
C15 H15A . 0.990000 ?
C15 H15B . 0.990000 ?
C16 C17 . 1.513(8) ?
C16 H16A . 0.990000 ?
C16 H16B . 0.990000 ?
C17 H17A . 0.990000 ?
C17 H17B . 0.990000 ?
C19 H19A . 0.980000 ?
C19 H19B . 0.980000 ?
C19 H19C . 0.980000 ?
C21 C22 . 1.512(8) ?
C21 C23 . 1.519(8) ?
C21 H21 . 1.000000 ?
C22 H22A . 0.980000 ?
C22 H22B . 0.980000 ?
C22 H22C . 0.980000 ?
C24 C28 . 1.524(8) ?
C24 C25 . 1.536(8) ?
C24 H24 . 1.000000 ?
C25 C26 . 1.528(8) ?
C25 H25A . 0.990000 ?
C25 H25B . 0.990000 ?
C26 C27 . 1.532(7) ?
C26 H26A . 0.990000 ?
C26 H26B . 0.990000 ?
C27 H27A . 0.990000 ?
C27 H27B . 0.990000 ?
C28 O9A . 1.196(15) ?
C28 O9 . 1.213(16) ?
C28 O10 . 1.295(11) ?
C28 O10A . 1.428(13) ?
O10 C29 . 1.442(17) ?
C29 H29A . 0.980000 ?
C29 H29B . 0.980000 ?
C29 H29C . 0.980000 ?
O10A C29A . 1.443(16) ?
C29A H29D . 0.980000 ?
C29A H29E . 0.980000 ?
C29A H29F . 0.980000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C23 N2 C24 . . 117.8(4) ?
C23 N2 C27 . . 129.2(4) ?
C24 N2 C27 . . 112.0(4) ?
C18 O6 C19 . . 116.5(4) ?
C6 O7 C21 . . 117.9(4) ?
C2 C1 C6 . . 125.1(7) ?
C2A C1 C6 . . 113.5(9) ?
C2 C1 I1 . . 114.6(7) ?
C2A C1 I1 . . 126.3(9) ?
C6 C1 I1 . . 120.2(3) ?
O7 C6 C1 . . 115.8(4) ?
O7 C6 C5A . . 116.8(10) ?
C1 C6 C5A . . 126.5(10) ?
O7 C6 C5 . . 128.0(7) ?
C1 C6 C5 . . 116.1(7) ?
C13A N1 C17 . . 127.0(10) ?
C13 N1 C17 . . 129.1(7) ?
C13A N1 C14 . . 119.7(10) ?
C13 N1 C14 . . 119.1(7) ?
C17 N1 C14 . . 111.7(4) ?
O3 C2 C1 . . 119.6(11) ?
O3 C2 C3 . . 122.2(10) ?
C1 C2 C3 . . 118.2(11) ?
C4 C3 C2 . . 117.4(10) ?
C4 C3 H3 . . 121.300000 ?
C2 C3 H3 . . 121.300000 ?
C3 C4 C5 . . 123.9(9) ?
C3 C4 C7 . . 118.5(10) ?
C5 C4 C7 . . 117.5(11) ?
C4 C5 C6 . . 119.3(10) ?
C4 C5 H5 . . 120.400000 ?
C6 C5 H5 . . 120.400000 ?
O1 C7 O2 . . 124.0(9) ?
O1 C7 C4 . . 125.2(12) ?
O2 C7 C4 . . 110.7(11) ?
C7 O2 C8 . . 116.6(10) ?
O2 C8 H8A . . 109.500000 ?
O2 C8 H8B . . 109.500000 ?
H8A C8 H8B . . 109.500000 ?
O2 C8 H8C . . 109.500000 ?
H8A C8 H8C . . 109.500000 ?
H8B C8 H8C . . 109.500000 ?
C2 O3 C11 . . 121.8(12) ?
O3 C11 C12 . . 106.7(10) ?
O3 C11 C13 . . 111.1(10) ?
C12 C11 C13 . . 110.5(12) ?
O3 C11 H11 . . 109.500000 ?
C12 C11 H11 . . 109.500000 ?
C13 C11 H11 . . 109.500000 ?
C11 C12 H12A . . 109.500000 ?
C11 C12 H12B . . 109.500000 ?
H12A C12 H12B . . 109.500000 ?
C11 C12 H12C . . 109.500000 ?
H12A C12 H12C . . 109.500000 ?
H12B C12 H12C . . 109.500000 ?
O4 C13 N1 . . 121.2(16) ?
O4 C13 C11 . . 121.8(15) ?
N1 C13 C11 . . 116.6(10) ?
O3A C2A C3A . . 128.0(17) ?
O3A C2A C1 . . 108.9(15) ?
C3A C2A C1 . . 122.4(16) ?
C2A C3A C4A . . 121.1(16) ?
C2A C3A H3A . . 119.500000 ?
C4A C3A H3A . . 119.500000 ?
C3A C4A C5A . . 119.3(14) ?
C3A C4A C7A . . 119.8(15) ?
C5A C4A C7A . . 120.9(15) ?
C4A C5A C6 . . 116.1(15) ?
C4A C5A H5A . . 121.900000 ?
C6 C5A H5A . . 121.900000 ?
O1A C7A O2A . . 122.7(15) ?
O1A C7A C4A . . 125.9(17) ?
O2A C7A C4A . . 111.3(17) ?
C7A O2A C8A . . 116.2(15) ?
O2A C8A H8A1 . . 109.500000 ?
O2A C8A H8A2 . . 109.500000 ?
H8A1 C8A H8A2 . . 109.500000 ?
O2A C8A H8A3 . . 109.500000 ?
H8A1 C8A H8A3 . . 109.500000 ?
H8A2 C8A H8A3 . . 109.500000 ?
C2A O3A C11A . . 121.0(19) ?
O3A C11A C12A . . 105.1(16) ?
O3A C11A C13A . . 108.8(17) ?
C12A C11A C13A . . 112.1(18) ?
O3A C11A H11A . . 110.200000 ?
C12A C11A H11A . . 110.200000 ?
C13A C11A H11A . . 110.200000 ?
C11A C12A H12D . . 109.500000 ?
C11A C12A H12E . . 109.500000 ?
H12D C12A H12E . . 109.500000 ?
C11A C12A H12F . . 109.500000 ?
H12D C12A H12F . . 109.500000 ?
H12E C12A H12F . . 109.500000 ?
O4A C13A N1 . . 121.(3) ?
O4A C13A C11A . . 122.(3) ?
N1 C13A C11A . . 115.4(15) ?
N1 C14 C18 . . 110.0(4) ?
N1 C14 C15 . . 103.1(4) ?
C18 C14 C15 . . 112.8(4) ?
N1 C14 H14 . . 110.200000 ?
C18 C14 H14 . . 110.200000 ?
C15 C14 H14 . . 110.200000 ?
C14 C15 C16 . . 103.3(4) ?
C14 C15 H15A . . 111.100000 ?
C16 C15 H15A . . 111.100000 ?
C14 C15 H15B . . 111.100000 ?
C16 C15 H15B . . 111.100000 ?
H15A C15 H15B . . 109.100000 ?
C17 C16 C15 . . 103.8(5) ?
C17 C16 H16A . . 111.000000 ?
C15 C16 H16A . . 111.000000 ?
C17 C16 H16B . . 111.000000 ?
C15 C16 H16B . . 111.000000 ?
H16A C16 H16B . . 109.000000 ?
N1 C17 C16 . . 103.7(5) ?
N1 C17 H17A . . 111.000000 ?
C16 C17 H17A . . 111.000000 ?
N1 C17 H17B . . 111.000000 ?
C16 C17 H17B . . 111.000000 ?
H17A C17 H17B . . 109.000000 ?
O5 C18 O6 . . 124.7(5) ?
O5 C18 C14 . . 125.0(5) ?
O6 C18 C14 . . 110.2(4) ?
O6 C19 H19A . . 109.500000 ?
O6 C19 H19B . . 109.500000 ?
H19A C19 H19B . . 109.500000 ?
O6 C19 H19C . . 109.500000 ?
H19A C19 H19C . . 109.500000 ?
H19B C19 H19C . . 109.500000 ?
O7 C21 C22 . . 107.0(4) ?
O7 C21 C23 . . 114.6(4) ?
C22 C21 C23 . . 110.2(4) ?
O7 C21 H21 . . 108.300000 ?
C22 C21 H21 . . 108.300000 ?
C23 C21 H21 . . 108.300000 ?
C21 C22 H22A . . 109.500000 ?
C21 C22 H22B . . 109.500000 ?
H22A C22 H22B . . 109.500000 ?
C21 C22 H22C . . 109.500000 ?
H22A C22 H22C . . 109.500000 ?
H22B C22 H22C . . 109.500000 ?
O8 C23 N2 . . 121.6(5) ?
O8 C23 C21 . . 117.9(5) ?
N2 C23 C21 . . 120.5(4) ?
N2 C24 C28 . . 109.5(5) ?
N2 C24 C25 . . 103.5(4) ?
C28 C24 C25 . . 111.9(4) ?
N2 C24 H24 . . 110.600000 ?
C28 C24 H24 . . 110.600000 ?
C25 C24 H24 . . 110.600000 ?
C26 C25 C24 . . 102.9(4) ?
C26 C25 H25A . . 111.200000 ?
C24 C25 H25A . . 111.200000 ?
C26 C25 H25B . . 111.200000 ?
C24 C25 H25B . . 111.200000 ?
H25A C25 H25B . . 109.100000 ?
C25 C26 C27 . . 104.2(4) ?
C25 C26 H26A . . 110.900000 ?
C27 C26 H26A . . 110.900000 ?
C25 C26 H26B . . 110.900000 ?
C27 C26 H26B . . 110.900000 ?
H26A C26 H26B . . 108.900000 ?
N2 C27 C26 . . 103.9(4) ?
N2 C27 H27A . . 111.000000 ?
C26 C27 H27A . . 111.000000 ?
N2 C27 H27B . . 111.000000 ?
C26 C27 H27B . . 111.000000 ?
H27A C27 H27B . . 109.000000 ?
O9 C28 O10 . . 121.4(19) ?
O9A C28 O10A . . 118.4(13) ?
O9A C28 C24 . . 132.4(15) ?
O9 C28 C24 . . 119.6(16) ?
O10 C28 C24 . . 114.8(7) ?
O10A C28 C24 . . 105.8(6) ?
C28 O10 C29 . . 115.6(10) ?
O10 C29 H29A . . 109.500000 ?
O10 C29 H29B . . 109.500000 ?
H29A C29 H29B . . 109.500000 ?
O10 C29 H29C . . 109.500000 ?
H29A C29 H29C . . 109.500000 ?
H29B C29 H29C . . 109.500000 ?
C28 O10A C29A . . 117.2(12) ?
O10A C29A H29D . . 109.500000 ?
O10A C29A H29E . . 109.500000 ?
H29D C29A H29E . . 109.500000 ?
O10A C29A H29F . . 109.500000 ?
H29D C29A H29F . . 109.500000 ?
H29E C29A H29F . . 109.500000 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C21 O7 C6 C1 . . . . -175.3(4) ?
C21 O7 C6 C5A . . . . 14.9(15) ?
C21 O7 C6 C5 . . . . -0.4(11) ?
C2 C1 C6 O7 . . . . 178.7(14) ?
C2A C1 C6 O7 . . . . -176.(2) ?
I1 C1 C6 O7 . . . . 2.5(6) ?
C2A C1 C6 C5A . . . . -7.(3) ?
I1 C1 C6 C5A . . . . 171.2(15) ?
C2 C1 C6 C5 . . . . 3.2(16) ?
I1 C1 C6 C5 . . . . -173.0(8) ?
C6 C1 C2 O3 . . . . 174.0(14) ?
I1 C1 C2 O3 . . . . -10.(3) ?
C6 C1 C2 C3 . . . . -3.(3) ?
I1 C1 C2 C3 . . . . 173.9(15) ?
O3 C2 C3 C4 . . . . -174.9(18) ?
C1 C2 C3 C4 . . . . 1.(3) ?
C2 C3 C4 C5 . . . . -1.(2) ?
C2 C3 C4 C7 . . . . 174.9(16) ?
C3 C4 C5 C6 . . . . 2.(2) ?
C7 C4 C5 C6 . . . . -174.1(11) ?
O7 C6 C5 C4 . . . . -177.8(9) ?
C1 C6 C5 C4 . . . . -2.9(16) ?
C3 C4 C7 O1 . . . . -144.3(13) ?
C5 C4 C7 O1 . . . . 32.3(17) ?
C3 C4 C7 O2 . . . . 36.3(14) ?
C5 C4 C7 O2 . . . . -147.1(11) ?
O1 C7 O2 C8 . . . . 7.4(14) ?
C4 C7 O2 C8 . . . . -173.2(8) ?
C1 C2 O3 C11 . . . . 173.0(15) ?
C3 C2 O3 C11 . . . . -11.(3) ?
C2 O3 C11 C12 . . . . -169.3(18) ?
C2 O3 C11 C13 . . . . 70.(2) ?
C17 N1 C13 O4 . . . . -177.(3) ?
C14 N1 C13 O4 . . . . 6.(4) ?
C17 N1 C13 C11 . . . . -3.(2) ?
C14 N1 C13 C11 . . . . 179.6(10) ?
O3 C11 C13 O4 . . . . 17.(4) ?
C12 C11 C13 O4 . . . . -101.(4) ?
O3 C11 C13 N1 . . . . -156.3(14) ?
C12 C11 C13 N1 . . . . 85.5(17) ?
C6 C1 C2A O3A . . . . -174.(3) ?
I1 C1 C2A O3A . . . . 7.(5) ?
C6 C1 C2A C3A . . . . -3.(5) ?
I1 C1 C2A C3A . . . . 179.(3) ?
O3A C2A C3A C4A . . . . 178.(4) ?
C1 C2A C3A C4A . . . . 8.(6) ?
C2A C3A C4A C5A . . . . -3.(4) ?
C2A C3A C4A C7A . . . . 173.(3) ?
C3A C4A C5A C6 . . . . -6.(3) ?
C7A C4A C5A C6 . . . . 178.(2) ?
O7 C6 C5A C4A . . . . -179.7(16) ?
C1 C6 C5A C4A . . . . 12.(3) ?
C3A C4A C7A O1A . . . . -163.(2) ?
C5A C4A C7A O1A . . . . 14.(4) ?
C3A C4A C7A O2A . . . . 20.(3) ?
C5A C4A C7A O2A . . . . -163.(2) ?
O1A C7A O2A C8A . . . . 3.(3) ?
C4A C7A O2A C8A . . . . -179.6(19) ?
C3A C2A O3A C11A . . . . -4.(7) ?
C1 C2A O3A C11A . . . . 167.(3) ?
C2A O3A C11A C12A . . . . -174.(3) ?
C2A O3A C11A C13A . . . . 66.(4) ?
C17 N1 C13A O4A . . . . 178.(6) ?
C14 N1 C13A O4A . . . . -18.(7) ?
C17 N1 C13A C11A . . . . 9.(3) ?
C14 N1 C13A C11A . . . . 173.6(14) ?
O3A C11A C13A O4A . . . . 16.(7) ?
C12A C11A C13A O4A . . . . -100.(7) ?
O3A C11A C13A N1 . . . . -175.(2) ?
C12A C11A C13A N1 . . . . 69.(3) ?
C13A N1 C14 C18 . . . . -59.7(17) ?
C13 N1 C14 C18 . . . . -75.1(11) ?
C17 N1 C14 C18 . . . . 107.2(6) ?
C13A N1 C14 C15 . . . . 179.7(16) ?
C13 N1 C14 C15 . . . . 164.4(11) ?
C17 N1 C14 C15 . . . . -13.4(6) ?
N1 C14 C15 C16 . . . . 31.4(5) ?
C18 C14 C15 C16 . . . . -87.3(5) ?
C14 C15 C16 C17 . . . . -38.3(6) ?
C13A N1 C17 C16 . . . . 155.5(18) ?
C13 N1 C17 C16 . . . . 172.2(12) ?
C14 N1 C17 C16 . . . . -10.3(7) ?
C15 C16 C17 N1 . . . . 29.8(7) ?
C19 O6 C18 O5 . . . . -1.0(7) ?
C19 O6 C18 C14 . . . . 177.2(4) ?
N1 C14 C18 O5 . . . . -30.6(7) ?
C15 C14 C18 O5 . . . . 84.0(6) ?
N1 C14 C18 O6 . . . . 151.3(4) ?
C15 C14 C18 O6 . . . . -94.2(5) ?
C6 O7 C21 C22 . . . . -170.2(4) ?
C6 O7 C21 C23 . . . . 67.3(5) ?
C24 N2 C23 O8 . . . . -5.6(7) ?
C27 N2 C23 O8 . . . . -173.1(5) ?
C24 N2 C23 C21 . . . . 171.4(5) ?
C27 N2 C23 C21 . . . . 3.9(8) ?
O7 C21 C23 O8 . . . . -148.2(4) ?
C22 C21 C23 O8 . . . . 91.1(5) ?
O7 C21 C23 N2 . . . . 34.7(6) ?
C22 C21 C23 N2 . . . . -86.1(6) ?
C23 N2 C24 C28 . . . . -67.5(5) ?
C27 N2 C24 C28 . . . . 102.1(5) ?
C23 N2 C24 C25 . . . . 173.1(4) ?
C27 N2 C24 C25 . . . . -17.3(5) ?
N2 C24 C25 C26 . . . . 32.9(5) ?
C28 C24 C25 C26 . . . . -84.9(5) ?
C24 C25 C26 C27 . . . . -36.6(6) ?
C23 N2 C27 C26 . . . . 162.7(5) ?
C24 N2 C27 C26 . . . . -5.4(5) ?
C25 C26 C27 N2 . . . . 26.2(5) ?
N2 C24 C28 O9A . . . . -19.(2) ?
C25 C24 C28 O9A . . . . 95.(2) ?
N2 C24 C28 O9 . . . . -6.(2) ?
C25 C24 C28 O9 . . . . 108.(2) ?
N2 C24 C28 O10 . . . . 151.0(10) ?
C25 C24 C28 O10 . . . . -94.9(10) ?
N2 C24 C28 O10A . . . . -176.8(8) ?
C25 C24 C28 O10A . . . . -62.7(9) ?
O9 C28 O10 C29 . . . . -21.(3) ?
C24 C28 O10 C29 . . . . -177.6(11) ?
O9A C28 O10A C29A . . . . 15.(3) ?
C24 C28 O10A C29A . . . . 176.4(12) ?



# start Validation Reply Form
_vrf_PLAT094_gil10466_23         
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PROBLEM: Ratio of Maximum / Minimum Residual Density ....       5.35 Report
RESPONSE: One badly disordered half heptane molecule was found in the 
asymmetrical unit and could not be satisfactorily refined. The program
SQUEEZE (Spek, A.L. (2015). Acta Cryst. C71, 9-18) was therefore used to
remove mathematically the effect of the solvent. Moreover, different 
parts of the molecule were found disordered over two positions in the 
asymmetric unit. Several restraints (SADI, SAME, ISOR and SIMU) were used
in order to improve refinement stability.    
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