# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_dan9754
_database_code_depnum_ccdc_archive 'CCDC 2056208'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2021-01-14 deposited with the CCDC.	2021-04-23 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H11 Cl O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         222.66

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   5.75830(10)
_cell_length_b                   9.7431(2)
_cell_length_c                   18.3135(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.0580(10)
_cell_angle_gamma                90
_cell_volume                     1024.88(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9930
_cell_measurement_theta_min      4.1185
_cell_measurement_theta_max      27.4714
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.194
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.098
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464

_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Mo ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            23308
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_theta_min         3.79
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23

_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             2335
_reflns_number_gt                2257
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0680
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_number_reflns         2335
_refine_ls_number_parameters     136
_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)+(0.0285P)²+0.5981P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.188
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;

APEX3 v2016.1-0 (Bruker AXS Inc., 2016)
;
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

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
Cl Cl1 0.01557(5) 0.58855(3) 0.34582(2) 0.01978(9) Uani d . . . 1 . .
O O1 -0.05981(14) 0.28461(9) 0.18635(4) 0.01853(18) Uani d . . . 1 . .
O O2 0.15325(13) 0.30825(8) 0.29197(4) 0.01428(17) Uani d . . . 1 . .
C C1 0.7687(2) 0.12008(13) 0.41189(7) 0.0218(2) Uani d . . . 1 . .
H H1 0.8884 0.0575 0.4014 0.026 Uiso calc U . R 1 . .
C C2 0.6942(2) 0.12728(13) 0.48244(7) 0.0229(2) Uani d . . . 1 . .
H H2 0.7636 0.069 0.5194 0.028 Uiso calc U . R 1 . .
C C3 0.5196(2) 0.21843(12) 0.49985(6) 0.0197(2) Uani d . . . 1 . .
H H3 0.4697 0.223 0.5481 0.024 Uiso calc U . R 1 . .
C C4 0.42049(19) 0.30248(11) 0.44462(6) 0.0157(2) Uani d . . . 1 . .
C C5 0.49499(18) 0.29416(11) 0.37377(6) 0.0139(2) Uani d . . . 1 . .
C C6 0.66935(19) 0.20381(12) 0.35642(6) 0.0170(2) Uani d . . . 1 . .
H H6 0.7194 0.1992 0.3082 0.02 Uiso calc U . R 1 . .
C C7 0.2304(2) 0.40898(12) 0.44815(6) 0.0177(2) Uani d . . . 1 . .
H H7A 0.2528 0.4661 0.4928 0.021 Uiso calc U . R 1 . .
H H7B 0.0741 0.3662 0.4461 0.021 Uiso calc U . R 1 . .
C C8 0.26673(18) 0.49242(11) 0.37885(6) 0.0152(2) Uani d . . . 1 . .
H H8 0.3957 0.5591 0.3909 0.018 Uiso calc U . R 1 . .
C C9 0.35262(18) 0.38885(11) 0.32292(6) 0.0130(2) Uani d . . . 1 . .
C C10 0.46563(19) 0.44915(12) 0.25643(6) 0.0159(2) Uani d . . . 1 . .
H H10A 0.5113 0.546 0.2654 0.019 Uiso calc U . R 1 . .
H H10B 0.6053 0.3958 0.2455 0.019 Uiso calc U . R 1 . .
C C11 0.2773(2) 0.43844(12) 0.19377(6) 0.0175(2) Uani d . . . 1 . .
H H11A 0.2036 0.5288 0.1835 0.021 Uiso calc U . R 1 . .
H H11B 0.3435 0.4045 0.1487 0.021 Uiso calc U . R 1 . .
C C12 0.10350(18) 0.33779(11) 0.22030(6) 0.0140(2) 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
Cl1 C8 . 1.7919(11) ?
O1 C12 . 1.2069(14) ?
O2 C12 . 1.3544(13) ?
O2 C9 . 1.4709(12) ?
C1 C2 . 1.3915(17) ?
C1 C6 . 1.3938(16) ?
C1 H1 . 0.95 ?
C2 C3 . 1.3951(17) ?
C2 H2 . 0.95 ?
C3 C4 . 1.3920(16) ?
C3 H3 . 0.95 ?
C4 C5 . 1.3974(15) ?
C4 C7 . 1.5128(15) ?
C5 C6 . 1.3889(15) ?
C5 C9 . 1.5108(15) ?
C6 H6 . 0.95 ?
C7 C8 . 1.5340(15) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C9 . 1.5439(14) ?
C8 H8 . 1.0 ?
C9 C10 . 1.5373(14) ?
C10 C11 . 1.5255(15) ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C11 C12 . 1.5062(15) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?

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
C12 O2 C9 . . 111.45(8) ?
C2 C1 C6 . . 120.65(11) ?
C2 C1 H1 . . 119.7 ?
C6 C1 H1 . . 119.7 ?
C1 C2 C3 . . 121.23(11) ?
C1 C2 H2 . . 119.4 ?
C3 C2 H2 . . 119.4 ?
C4 C3 C2 . . 118.27(11) ?
C4 C3 H3 . . 120.9 ?
C2 C3 H3 . . 120.9 ?
C3 C4 C5 . . 120.23(10) ?
C3 C4 C7 . . 129.28(10) ?
C5 C4 C7 . . 110.49(9) ?
C6 C5 C4 . . 121.58(10) ?
C6 C5 C9 . . 127.98(10) ?
C4 C5 C9 . . 110.37(9) ?
C5 C6 C1 . . 118.04(10) ?
C5 C6 H6 . . 121.0 ?
C1 C6 H6 . . 121.0 ?
C4 C7 C8 . . 100.77(8) ?
C4 C7 H7A . . 111.6 ?
C8 C7 H7A . . 111.6 ?
C4 C7 H7B . . 111.6 ?
C8 C7 H7B . . 111.6 ?
H7A C7 H7B . . 109.4 ?
C7 C8 C9 . . 105.74(9) ?
C7 C8 Cl1 . . 113.72(8) ?
C9 C8 Cl1 . . 113.98(7) ?
C7 C8 H8 . . 107.7 ?
C9 C8 H8 . . 107.7 ?
Cl1 C8 H8 . . 107.7 ?
O2 C9 C5 . . 106.63(8) ?
O2 C9 C10 . . 105.16(8) ?
C5 C9 C10 . . 118.68(9) ?
O2 C9 C8 . . 109.06(8) ?
C5 C9 C8 . . 100.11(8) ?
C10 C9 C8 . . 116.68(9) ?
C11 C10 C9 . . 104.56(8) ?
C11 C10 H10A . . 110.8 ?
C9 C10 H10A . . 110.8 ?
C11 C10 H10B . . 110.8 ?
C9 C10 H10B . . 110.8 ?
H10A C10 H10B . . 108.9 ?
C12 C11 C10 . . 104.78(9) ?
C12 C11 H11A . . 110.8 ?
C10 C11 H11A . . 110.8 ?
C12 C11 H11B . . 110.8 ?
C10 C11 H11B . . 110.8 ?
H11A C11 H11B . . 108.9 ?
O1 C12 O2 . . 120.77(10) ?
O1 C12 C11 . . 128.66(10) ?
O2 C12 C11 . . 110.56(9) ?

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
C6 C1 C2 C3 . . . . -0.30(19) ?
C1 C2 C3 C4 . . . . 0.12(18) ?
C2 C3 C4 C5 . . . . 0.28(17) ?
C2 C3 C4 C7 . . . . 179.88(11) ?
C3 C4 C5 C6 . . . . -0.52(16) ?
C7 C4 C5 C6 . . . . 179.82(10) ?
C3 C4 C5 C9 . . . . 176.67(10) ?
C7 C4 C5 C9 . . . . -3.00(12) ?
C4 C5 C6 C1 . . . . 0.34(16) ?
C9 C5 C6 C1 . . . . -176.31(10) ?
C2 C1 C6 C5 . . . . 0.07(18) ?
C3 C4 C7 C8 . . . . 161.66(11) ?
C5 C4 C7 C8 . . . . -18.71(12) ?
C4 C7 C8 C9 . . . . 32.89(10) ?
C4 C7 C8 Cl1 . . . . 158.70(7) ?
C12 O2 C9 C5 . . . . -140.77(9) ?
C12 O2 C9 C10 . . . . -13.91(11) ?
C12 O2 C9 C8 . . . . 111.95(9) ?
C6 C5 C9 O2 . . . . 86.54(12) ?
C4 C5 C9 O2 . . . . -90.42(10) ?
C6 C5 C9 C10 . . . . -31.79(16) ?
C4 C5 C9 C10 . . . . 151.26(10) ?
C6 C5 C9 C8 . . . . -159.91(11) ?
C4 C5 C9 C8 . . . . 23.13(11) ?
C7 C8 C9 O2 . . . . 77.23(10) ?
Cl1 C8 C9 O2 . . . . -48.43(10) ?
C7 C8 C9 C5 . . . . -34.44(10) ?
Cl1 C8 C9 C5 . . . . -160.09(7) ?
C7 C8 C9 C10 . . . . -163.87(9) ?
Cl1 C8 C9 C10 . . . . 70.48(11) ?
O2 C9 C10 C11 . . . . 18.51(11) ?
C5 C9 C10 C11 . . . . 137.60(10) ?
C8 C9 C10 C11 . . . . -102.48(10) ?
C9 C10 C11 C12 . . . . -16.62(11) ?
C9 O2 C12 O1 . . . . -177.60(9) ?
C9 O2 C12 C11 . . . . 3.20(11) ?
C10 C11 C12 O1 . . . . -170.18(11) ?
C10 C11 C12 O2 . . . . 8.94(12) ?


####################################################################### 
# 
# 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_dan9759
_database_code_depnum_ccdc_archive 'CCDC 2056209'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2021-01-14 deposited with the CCDC.	2021-04-23 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H11 Cl O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         222.66

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1989(4)
_cell_length_b                   8.4173(4)
_cell_length_c                   8.8635(4)
_cell_angle_alpha                68.933(2)
_cell_angle_beta                 76.834(2)
_cell_angle_gamma                65.982(2)
_cell_volume                     519.00(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4281
_cell_measurement_theta_min      2.7323
_cell_measurement_theta_max      27.8561
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.109
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.043
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             232

_exptl_absorpt_coefficient_mu    0.342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Mo ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            9720
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         26.73
_diffrn_reflns_theta_full        26.73
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

_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             2161
_reflns_number_gt                1950
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_gt          0.0813
_refine_ls_wR_factor_ref         0.0838
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.140
_refine_ls_number_reflns         2161
_refine_ls_number_parameters     136
_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)+(0.0245P)²+0.3961P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.209
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;

APEX3 v2016.1-0 (Bruker AXS Inc., 2016)
;
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

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
Cl Cl1 0.04558(6) 0.68012(6) 0.81080(6) 0.02163(13) Uani d . . . 1 . .
O O1 0.33123(17) 1.11091(17) 0.64164(16) 0.0217(3) Uani d . . . 1 . .
O O2 0.41413(16) 0.80952(16) 0.75093(14) 0.0143(3) Uani d . . . 1 . .
C C1 0.8981(3) 0.3353(3) 0.7320(2) 0.0194(4) Uani d . . . 1 . .
H H1 1.0168 0.3345 0.6969 0.023 Uiso calc U . R 1 . .
C C2 0.8695(3) 0.1723(3) 0.8198(2) 0.0203(4) Uani d . . . 1 . .
H H2 0.9695 0.0612 0.8428 0.024 Uiso calc U . R 1 . .
C C3 0.6975(3) 0.1699(2) 0.8740(2) 0.0182(4) Uani d . . . 1 . .
H H3 0.6795 0.0585 0.9342 0.022 Uiso calc U . R 1 . .
C C4 0.5518(2) 0.3330(2) 0.8388(2) 0.0154(4) Uani d . . . 1 . .
C C5 0.5814(2) 0.4953(2) 0.75041(19) 0.0135(3) Uani d . . . 1 . .
C C6 0.7527(2) 0.4989(2) 0.6959(2) 0.0160(4) Uani d . . . 1 . .
H H6 0.7705 0.6103 0.6355 0.019 Uiso calc U . R 1 . .
C C7 0.3534(2) 0.3686(2) 0.8807(2) 0.0179(4) Uani d . . . 1 . .
H H7A 0.3273 0.3002 0.9946 0.022 Uiso calc U . R 1 . .
H H7B 0.3058 0.3363 0.8073 0.022 Uiso calc U . R 1 . .
C C8 0.2761(2) 0.5753(2) 0.8551(2) 0.0150(4) Uani d . . . 1 . .
H H8 0.2827 0.5956 0.9577 0.018 Uiso calc U . R 1 . .
C C9 0.4052(2) 0.6532(2) 0.7214(2) 0.0130(3) Uani d . . . 1 . .
C C10 0.3556(2) 0.7260(2) 0.5450(2) 0.0156(4) Uani d . . . 1 . .
H H10A 0.4641 0.6964 0.4683 0.019 Uiso calc U . R 1 . .
H H10B 0.2722 0.6737 0.5335 0.019 Uiso calc U . R 1 . .
C C11 0.2657(2) 0.9315(2) 0.5146(2) 0.0183(4) Uani d . . . 1 . .
H H11A 0.2991 0.9983 0.4023 0.022 Uiso calc U . R 1 . .
H H11B 0.1335 0.9679 0.5326 0.022 Uiso calc U . R 1 . .
C C12 0.3363(2) 0.9679(2) 0.6364(2) 0.0154(4) 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
Cl1 C8 . 1.7992(18) ?
O1 C12 . 1.205(2) ?
O2 C12 . 1.358(2) ?
O2 C9 . 1.463(2) ?
C1 C6 . 1.393(3) ?
C1 C2 . 1.398(3) ?
C1 H1 . 0.95 ?
C2 C3 . 1.388(3) ?
C2 H2 . 0.95 ?
C3 C4 . 1.391(3) ?
C3 H3 . 0.95 ?
C4 C5 . 1.397(2) ?
C4 C7 . 1.510(2) ?
C5 C6 . 1.386(2) ?
C5 C9 . 1.510(2) ?
C6 H6 . 0.95 ?
C7 C8 . 1.537(2) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C9 . 1.546(2) ?
C8 H8 . 1.0 ?
C9 C10 . 1.544(2) ?
C10 C11 . 1.525(3) ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C11 C12 . 1.505(2) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?

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
C12 O2 C9 . . 111.56(13) ?
C6 C1 C2 . . 120.07(17) ?
C6 C1 H1 . . 120.0 ?
C2 C1 H1 . . 120.0 ?
C3 C2 C1 . . 121.11(17) ?
C3 C2 H2 . . 119.4 ?
C1 C2 H2 . . 119.4 ?
C2 C3 C4 . . 119.07(17) ?
C2 C3 H3 . . 120.5 ?
C4 C3 H3 . . 120.5 ?
C3 C4 C5 . . 119.48(17) ?
C3 C4 C7 . . 129.92(16) ?
C5 C4 C7 . . 110.59(15) ?
C6 C5 C4 . . 121.84(16) ?
C6 C5 C9 . . 127.65(16) ?
C4 C5 C9 . . 110.47(15) ?
C5 C6 C1 . . 118.43(17) ?
C5 C6 H6 . . 120.8 ?
C1 C6 H6 . . 120.8 ?
C4 C7 C8 . . 101.87(14) ?
C4 C7 H7A . . 111.4 ?
C8 C7 H7A . . 111.4 ?
C4 C7 H7B . . 111.4 ?
C8 C7 H7B . . 111.4 ?
H7A C7 H7B . . 109.3 ?
C7 C8 C9 . . 105.67(14) ?
C7 C8 Cl1 . . 113.28(12) ?
C9 C8 Cl1 . . 114.04(12) ?
C7 C8 H8 . . 107.9 ?
C9 C8 H8 . . 107.9 ?
Cl1 C8 H8 . . 107.9 ?
O2 C9 C5 . . 109.99(13) ?
O2 C9 C10 . . 104.51(13) ?
C5 C9 C10 . . 114.26(14) ?
O2 C9 C8 . . 109.67(13) ?
C5 C9 C8 . . 101.44(13) ?
C10 C9 C8 . . 116.99(14) ?
C11 C10 C9 . . 103.90(14) ?
C11 C10 H10A . . 111.0 ?
C9 C10 H10A . . 111.0 ?
C11 C10 H10B . . 111.0 ?
C9 C10 H10B . . 111.0 ?
H10A C10 H10B . . 109.0 ?
C12 C11 C10 . . 103.96(14) ?
C12 C11 H11A . . 111.0 ?
C10 C11 H11A . . 111.0 ?
C12 C11 H11B . . 111.0 ?
C10 C11 H11B . . 111.0 ?
H11A C11 H11B . . 109.0 ?
O1 C12 O2 . . 120.72(16) ?
O1 C12 C11 . . 129.04(17) ?
O2 C12 C11 . . 110.25(15) ?

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
C6 C1 C2 C3 . . . . -0.7(3) ?
C1 C2 C3 C4 . . . . 0.4(3) ?
C2 C3 C4 C5 . . . . -0.2(2) ?
C2 C3 C4 C7 . . . . 179.26(17) ?
C3 C4 C5 C6 . . . . 0.1(3) ?
C7 C4 C5 C6 . . . . -179.40(15) ?
C3 C4 C5 C9 . . . . 177.99(15) ?
C7 C4 C5 C9 . . . . -1.54(19) ?
C4 C5 C6 C1 . . . . -0.4(3) ?
C9 C5 C6 C1 . . . . -177.82(16) ?
C2 C1 C6 C5 . . . . 0.6(3) ?
C3 C4 C7 C8 . . . . 162.77(17) ?
C5 C4 C7 C8 . . . . -17.75(18) ?
C4 C7 C8 C9 . . . . 29.70(17) ?
C4 C7 C8 Cl1 . . . . 155.24(11) ?
C12 O2 C9 C5 . . . . 137.97(14) ?
C12 O2 C9 C10 . . . . 14.90(17) ?
C12 O2 C9 C8 . . . . -111.28(15) ?
C6 C5 C9 O2 . . . . -46.3(2) ?
C4 C5 C9 O2 . . . . 136.04(14) ?
C6 C5 C9 C10 . . . . 70.9(2) ?
C4 C5 C9 C10 . . . . -106.81(16) ?
C6 C5 C9 C8 . . . . -162.30(17) ?
C4 C5 C9 C8 . . . . 20.00(17) ?
C7 C8 C9 O2 . . . . -146.77(13) ?
Cl1 C8 C9 O2 . . . . 88.16(14) ?
C7 C8 C9 C5 . . . . -30.49(16) ?
Cl1 C8 C9 C5 . . . . -155.56(12) ?
C7 C8 C9 C10 . . . . 94.50(17) ?
Cl1 C8 C9 C10 . . . . -30.57(19) ?
O2 C9 C10 C11 . . . . -23.02(16) ?
C5 C9 C10 C11 . . . . -143.29(15) ?
C8 C9 C10 C11 . . . . 98.44(17) ?
C9 C10 C11 C12 . . . . 22.70(17) ?
C9 O2 C12 O1 . . . . 179.95(15) ?
C9 O2 C12 C11 . . . . -0.15(18) ?
C10 C11 C12 O1 . . . . 165.07(18) ?
C10 C11 C12 O2 . . . . -14.81(18) ?


####################################################################### 
# 
# 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_dan9940
_database_code_depnum_ccdc_archive 'CCDC 2056212'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2021-01-14 deposited with the CCDC.	2021-04-23 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2019.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H13 Cl O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         236.68

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5302(3)
_cell_length_b                   8.5648(3)
_cell_length_c                   8.8272(3)
_cell_angle_alpha                76.7530(10)
_cell_angle_beta                 69.1750(10)
_cell_angle_gamma                65.8030(10)
_cell_volume                     547.18(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5764
_cell_measurement_theta_min      5.9513
_cell_measurement_theta_max      66.9011
_cell_measurement_temperature    101.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.057
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             248

_exptl_absorpt_coefficient_mu    2.933
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 Bruker AXS area detector scaling and absorption correction.
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_T_max  0.85

_exptl_special_details           
;
;

_diffrn_ambient_temperature      101.(2)

_diffrn_source                   'Cu Ims'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON III Diffractometer'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            7594
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_theta_min         5.39
_diffrn_reflns_theta_max         66.92
_diffrn_reflns_theta_full        66.92
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10

_refine_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

Structure factors included contributions from the .fab file.

_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             1910
_reflns_number_gt                1828
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0711
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_number_reflns         1910
_refine_ls_number_parameters     145
_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)+(0.0309P)²+0.2414P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.224
_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'
Cl Cl 0.3639 0.7018 '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       'APEX3 v2019.1-0'
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  ?

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
Cl Cl1 0.23962(4) 0.96487(4) 0.20827(4) 0.02037(13) Uani d . . . 1 . .
O O1 0.19497(12) 0.60838(12) 0.24525(10) 0.0150(2) Uani d . . . 1 . .
O O2 -0.09987(13) 0.67599(13) 0.35719(12) 0.0222(2) Uani d . . . 1 . .
C C1 0.46139(18) 0.28950(18) 0.30705(15) 0.0165(3) Uani d . . . 1 . .
H H1 0.340952 0.299098 0.365752 0.02 Uiso calc U . R 1 . .
C C2 0.5949(2) 0.12818(17) 0.28608(16) 0.0191(3) Uani d . . . 1 . .
H H2 0.566217 0.027863 0.330851 0.023 Uiso calc U . R 1 . .
C C3 0.77120(19) 0.11352(18) 0.19927(16) 0.0192(3) Uani d . . . 1 . .
H H3 0.863179 0.003192 0.183687 0.023 Uiso calc U . R 1 . .
C C4 0.81200(18) 0.26036(18) 0.13570(16) 0.0178(3) Uani d . . . 1 . .
H H4 0.932622 0.249608 0.076421 0.021 Uiso calc U . R 1 . .
C C5 0.67911(18) 0.42444(17) 0.15698(15) 0.0145(3) Uani d . . . 1 . .
C C6 0.50176(17) 0.43890(17) 0.24269(15) 0.0130(3) Uani d . . . 1 . .
C C7 0.73172(18) 0.58073(17) 0.08736(16) 0.0166(3) Uani d . . . 1 . .
H H7A 0.753766 0.596484 -0.032094 0.02 Uiso calc U . R 1 . .
H H7B 0.845356 0.560596 0.108394 0.02 Uiso calc U . R 1 . .
C C8 0.58807(18) 0.74448(17) 0.15989(16) 0.0158(3) Uani d . . . 1 . .
H H8A 0.586834 0.743009 0.272776 0.019 Uiso calc U . R 1 . .
H H8B 0.614414 0.846268 0.094771 0.019 Uiso calc U . R 1 . .
C C9 0.40679(17) 0.75421(16) 0.15912(16) 0.0148(3) Uani d . . . 1 . .
H H9 0.417154 0.737865 0.046886 0.018 Uiso calc U . R 1 . .
C C10 0.35020(17) 0.61267(17) 0.27744(15) 0.0133(3) Uani d . . . 1 . .
C C11 0.28170(17) 0.64368(17) 0.45986(15) 0.0153(3) Uani d . . . 1 . .
H H11A 0.323887 0.534855 0.527795 0.018 Uiso calc U . R 1 . .
H H11B 0.324565 0.727619 0.477258 0.018 Uiso calc U . R 1 . .
C C12 0.07723(18) 0.71428(18) 0.50162(16) 0.0173(3) Uani d . . . 1 . .
H H12A 0.022861 0.660769 0.608495 0.021 Uiso calc U . R 1 . .
H H12B 0.028349 0.840576 0.50461 0.021 Uiso calc U . R 1 . .
C C13 0.04109(18) 0.66710(16) 0.36636(16) 0.0157(3) 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
Cl1 C9 . 1.8129(13) ?
O1 C13 . 1.3514(16) ?
O1 C10 . 1.4655(15) ?
O2 C13 . 1.2040(17) ?
C1 C2 . 1.385(2) ?
C1 C6 . 1.4027(19) ?
C1 H1 . 0.95 ?
C2 C3 . 1.391(2) ?
C2 H2 . 0.95 ?
C3 C4 . 1.384(2) ?
C3 H3 . 0.95 ?
C4 C5 . 1.3996(19) ?
C4 H4 . 0.95 ?
C5 C6 . 1.3971(19) ?
C5 C7 . 1.5134(18) ?
C6 C10 . 1.5266(18) ?
C7 C8 . 1.5242(18) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C9 . 1.5165(18) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C9 C10 . 1.5279(18) ?
C9 H9 . 1.0 ?
C10 C11 . 1.5507(17) ?
C11 C12 . 1.5246(18) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 C13 . 1.5063(19) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?

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
C13 O1 C10 . . 112.26(10) ?
C2 C1 C6 . . 120.82(13) ?
C2 C1 H1 . . 119.6 ?
C6 C1 H1 . . 119.6 ?
C1 C2 C3 . . 119.78(13) ?
C1 C2 H2 . . 120.1 ?
C3 C2 H2 . . 120.1 ?
C4 C3 C2 . . 119.69(13) ?
C4 C3 H3 . . 120.2 ?
C2 C3 H3 . . 120.2 ?
C3 C4 C5 . . 121.31(13) ?
C3 C4 H4 . . 119.3 ?
C5 C4 H4 . . 119.3 ?
C6 C5 C4 . . 118.91(12) ?
C6 C5 C7 . . 121.97(12) ?
C4 C5 C7 . . 119.12(12) ?
C5 C6 C1 . . 119.48(12) ?
C5 C6 C10 . . 122.24(11) ?
C1 C6 C10 . . 118.20(11) ?
C5 C7 C8 . . 112.65(11) ?
C5 C7 H7A . . 109.1 ?
C8 C7 H7A . . 109.1 ?
C5 C7 H7B . . 109.1 ?
C8 C7 H7B . . 109.1 ?
H7A C7 H7B . . 107.8 ?
C9 C8 C7 . . 108.61(11) ?
C9 C8 H8A . . 110.0 ?
C7 C8 H8A . . 110.0 ?
C9 C8 H8B . . 110.0 ?
C7 C8 H8B . . 110.0 ?
H8A C8 H8B . . 108.3 ?
C8 C9 C10 . . 111.23(11) ?
C8 C9 Cl1 . . 109.78(9) ?
C10 C9 Cl1 . . 110.87(9) ?
C8 C9 H9 . . 108.3 ?
C10 C9 H9 . . 108.3 ?
Cl1 C9 H9 . . 108.3 ?
O1 C10 C6 . . 107.39(10) ?
O1 C10 C9 . . 107.66(10) ?
C6 C10 C9 . . 109.37(10) ?
O1 C10 C11 . . 104.24(10) ?
C6 C10 C11 . . 112.65(10) ?
C9 C10 C11 . . 115.04(11) ?
C12 C11 C10 . . 104.93(10) ?
C12 C11 H11A . . 110.8 ?
C10 C11 H11A . . 110.8 ?
C12 C11 H11B . . 110.8 ?
C10 C11 H11B . . 110.8 ?
H11A C11 H11B . . 108.8 ?
C13 C12 C11 . . 104.27(10) ?
C13 C12 H12A . . 110.9 ?
C11 C12 H12A . . 110.9 ?
C13 C12 H12B . . 110.9 ?
C11 C12 H12B . . 110.9 ?
H12A C12 H12B . . 108.9 ?
O2 C13 O1 . . 120.73(12) ?
O2 C13 C12 . . 128.62(12) ?
O1 C13 C12 . . 110.65(11) ?

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
C6 C1 C2 C3 . . . . -0.4(2) ?
C1 C2 C3 C4 . . . . 0.5(2) ?
C2 C3 C4 C5 . . . . 0.1(2) ?
C3 C4 C5 C6 . . . . -0.75(19) ?
C3 C4 C5 C7 . . . . 178.95(12) ?
C4 C5 C6 C1 . . . . 0.84(18) ?
C7 C5 C6 C1 . . . . -178.85(11) ?
C4 C5 C6 C10 . . . . 177.40(11) ?
C7 C5 C6 C10 . . . . -2.29(18) ?
C2 C1 C6 C5 . . . . -0.26(19) ?
C2 C1 C6 C10 . . . . -176.96(11) ?
C6 C5 C7 C8 . . . . 16.12(17) ?
C4 C5 C7 C8 . . . . -163.57(11) ?
C5 C7 C8 C9 . . . . -46.94(14) ?
C7 C8 C9 C10 . . . . 67.58(13) ?
C7 C8 C9 Cl1 . . . . -169.34(9) ?
C13 O1 C10 C6 . . . . 132.81(10) ?
C13 O1 C10 C9 . . . . -109.52(11) ?
C13 O1 C10 C11 . . . . 13.09(13) ?
C5 C6 C10 O1 . . . . 136.31(12) ?
C1 C6 C10 O1 . . . . -47.08(14) ?
C5 C6 C10 C9 . . . . 19.76(16) ?
C1 C6 C10 C9 . . . . -163.64(11) ?
C5 C6 C10 C11 . . . . -109.49(13) ?
C1 C6 C10 C11 . . . . 67.11(14) ?
C8 C9 C10 O1 . . . . -168.51(10) ?
Cl1 C9 C10 O1 . . . . 69.03(11) ?
C8 C9 C10 C6 . . . . -52.13(13) ?
Cl1 C9 C10 C6 . . . . -174.59(8) ?
C8 C9 C10 C11 . . . . 75.79(14) ?
Cl1 C9 C10 C11 . . . . -46.67(13) ?
O1 C10 C11 C12 . . . . -18.66(13) ?
C6 C10 C11 C12 . . . . -134.76(11) ?
C9 C10 C11 C12 . . . . 98.98(13) ?
C10 C11 C12 C13 . . . . 17.58(13) ?
C10 O1 C13 O2 . . . . 178.22(12) ?
C10 O1 C13 C12 . . . . -1.84(14) ?
C11 C12 C13 O2 . . . . 169.50(13) ?
C11 C12 C13 O1 . . . . -10.43(14) ?


####################################################################### 
# 
# 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_dan9755
_database_code_depnum_ccdc_archive 'CCDC 2056211'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2021-01-14 deposited with the CCDC.	2021-04-23 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H11 Br O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         267.12

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3537(2)
_cell_length_b                   8.5198(2)
_cell_length_c                   8.8355(3)
_cell_angle_alpha                69.1250(10)
_cell_angle_beta                 76.7640(10)
_cell_angle_gamma                65.2120(10)
_cell_volume                     531.08(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7218
_cell_measurement_theta_min      2.4780
_cell_measurement_theta_max      27.5132
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.278
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.165
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             268

_exptl_absorpt_coefficient_mu    3.845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.53
_exptl_absorpt_correction_T_max  0.57

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Mo ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            9320
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

_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             2413
_reflns_number_gt                2333
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0165
_refine_ls_R_factor_gt           0.0156
_refine_ls_wR_factor_gt          0.0373
_refine_ls_wR_factor_ref         0.0376
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_number_reflns         2413
_refine_ls_number_parameters     136
_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)+(0.0139P)²+0.2965P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.223
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;

APEX3 v2016.1-0 (Bruker AXS Inc., 2016)
;
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

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 0.96370(2) 0.31306(2) 0.19586(2) 0.01951(5) Uani d . . . 1 . .
O O1 0.67078(12) -0.10802(12) 0.35820(12) 0.0218(2) Uani d . . . 1 . .
O O2 0.58618(11) 0.19086(11) 0.24965(10) 0.01411(17) Uani d . . . 1 . .
C C1 0.10200(17) 0.66024(18) 0.27036(16) 0.0187(3) Uani d . . . 1 . .
H H1 -0.0144 0.6607 0.3057 0.022 Uiso calc U . R 1 . .
C C2 0.12657(17) 0.82226(17) 0.18247(16) 0.0193(3) Uani d . . . 1 . .
H H2 0.0263 0.9319 0.159 0.023 Uiso calc U . R 1 . .
C C3 0.29580(17) 0.82574(17) 0.12859(15) 0.0177(2) Uani d . . . 1 . .
H H3 0.3117 0.9363 0.0689 0.021 Uiso calc U . R 1 . .
C C4 0.44118(16) 0.66337(16) 0.16416(14) 0.0140(2) Uani d . . . 1 . .
C C5 0.41566(16) 0.50268(16) 0.25182(14) 0.0126(2) Uani d . . . 1 . .
C C6 0.24729(16) 0.49801(17) 0.30656(15) 0.0157(2) Uani d . . . 1 . .
H H6 0.2318 0.3873 0.3669 0.019 Uiso calc U . R 1 . .
C C7 0.63646(16) 0.62971(16) 0.12264(16) 0.0166(2) Uani d . . . 1 . .
H H7A 0.6814 0.6629 0.1966 0.02 Uiso calc U . R 1 . .
H H7B 0.6616 0.6971 0.0087 0.02 Uiso calc U . R 1 . .
C C8 0.71601(15) 0.42417(16) 0.14858(14) 0.0137(2) Uani d . . . 1 . .
H H8 0.7109 0.4035 0.0456 0.016 Uiso calc U . R 1 . .
C C9 0.59064(15) 0.34583(16) 0.28161(14) 0.0118(2) Uani d . . . 1 . .
C C10 0.63574(16) 0.27485(16) 0.45925(14) 0.0148(2) Uani d . . . 1 . .
H H10A 0.7162 0.3263 0.4728 0.018 Uiso calc U . R 1 . .
H H10B 0.5271 0.3054 0.5343 0.018 Uiso calc U . R 1 . .
C C11 0.72648(17) 0.07034(17) 0.49039(15) 0.0175(2) Uani d . . . 1 . .
H H11A 0.857 0.0332 0.4755 0.021 Uiso calc U . R 1 . .
H H11B 0.6914 0.0051 0.6019 0.021 Uiso calc U . R 1 . .
C C12 0.66190(15) 0.03404(16) 0.36492(15) 0.0153(2) 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 C8 . 1.9554(12) ?
O1 C12 . 1.2032(16) ?
O2 C12 . 1.3562(15) ?
O2 C9 . 1.4615(14) ?
C1 C6 . 1.3935(17) ?
C1 C2 . 1.3968(19) ?
C1 H1 . 0.95 ?
C2 C3 . 1.3939(19) ?
C2 H2 . 0.95 ?
C3 C4 . 1.3941(17) ?
C3 H3 . 0.95 ?
C4 C5 . 1.3903(17) ?
C4 C7 . 1.5122(17) ?
C5 C6 . 1.3913(17) ?
C5 C9 . 1.5097(16) ?
C6 H6 . 0.95 ?
C7 C8 . 1.5391(17) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C9 . 1.5451(16) ?
C8 H8 . 1.0 ?
C9 C10 . 1.5409(16) ?
C10 C11 . 1.5273(17) ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C11 C12 . 1.5079(18) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?

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
C12 O2 C9 . . 111.59(9) ?
C6 C1 C2 . . 120.39(12) ?
C6 C1 H1 . . 119.8 ?
C2 C1 H1 . . 119.8 ?
C3 C2 C1 . . 121.09(12) ?
C3 C2 H2 . . 119.5 ?
C1 C2 H2 . . 119.5 ?
C2 C3 C4 . . 118.55(12) ?
C2 C3 H3 . . 120.7 ?
C4 C3 H3 . . 120.7 ?
C5 C4 C3 . . 120.03(12) ?
C5 C4 C7 . . 110.69(10) ?
C3 C4 C7 . . 129.27(11) ?
C4 C5 C6 . . 121.82(11) ?
C4 C5 C9 . . 110.98(10) ?
C6 C5 C9 . . 127.16(11) ?
C5 C6 C1 . . 118.12(12) ?
C5 C6 H6 . . 120.9 ?
C1 C6 H6 . . 120.9 ?
C4 C7 C8 . . 101.40(10) ?
C4 C7 H7A . . 111.5 ?
C8 C7 H7A . . 111.5 ?
C4 C7 H7B . . 111.5 ?
C8 C7 H7B . . 111.5 ?
H7A C7 H7B . . 109.3 ?
C7 C8 C9 . . 106.14(9) ?
C7 C8 Br1 . . 113.08(8) ?
C9 C8 Br1 . . 114.37(8) ?
C7 C8 H8 . . 107.6 ?
C9 C8 H8 . . 107.6 ?
Br1 C8 H8 . . 107.6 ?
O2 C9 C5 . . 110.18(9) ?
O2 C9 C10 . . 104.75(9) ?
C5 C9 C10 . . 113.68(10) ?
O2 C9 C8 . . 109.41(9) ?
C5 C9 C8 . . 100.97(9) ?
C10 C9 C8 . . 117.85(10) ?
C11 C10 C9 . . 103.92(10) ?
C11 C10 H10A . . 111.0 ?
C9 C10 H10A . . 111.0 ?
C11 C10 H10B . . 111.0 ?
C9 C10 H10B . . 111.0 ?
H10A C10 H10B . . 109.0 ?
C12 C11 C10 . . 103.87(10) ?
C12 C11 H11A . . 111.0 ?
C10 C11 H11A . . 111.0 ?
C12 C11 H11B . . 111.0 ?
C10 C11 H11B . . 111.0 ?
H11A C11 H11B . . 109.0 ?
O1 C12 O2 . . 120.93(12) ?
O1 C12 C11 . . 128.82(12) ?
O2 C12 C11 . . 110.24(10) ?

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
C6 C1 C2 C3 . . . . 0.23(19) ?
C1 C2 C3 C4 . . . . 0.05(19) ?
C2 C3 C4 C5 . . . . -0.11(18) ?
C2 C3 C4 C7 . . . . -179.14(12) ?
C3 C4 C5 C6 . . . . -0.12(18) ?
C7 C4 C5 C6 . . . . 179.09(11) ?
C3 C4 C5 C9 . . . . -177.83(11) ?
C7 C4 C5 C9 . . . . 1.37(14) ?
C4 C5 C6 C1 . . . . 0.39(18) ?
C9 C5 C6 C1 . . . . 177.71(11) ?
C2 C1 C6 C5 . . . . -0.44(18) ?
C5 C4 C7 C8 . . . . 17.71(13) ?
C3 C4 C7 C8 . . . . -163.18(12) ?
C4 C7 C8 C9 . . . . -29.59(12) ?
C4 C7 C8 Br1 . . . . -155.77(8) ?
C12 O2 C9 C5 . . . . -137.32(10) ?
C12 O2 C9 C10 . . . . -14.70(12) ?
C12 O2 C9 C8 . . . . 112.53(10) ?
C4 C5 C9 O2 . . . . -135.29(10) ?
C6 C5 C9 O2 . . . . 47.14(15) ?
C4 C5 C9 C10 . . . . 107.49(12) ?
C6 C5 C9 C10 . . . . -70.07(15) ?
C4 C5 C9 C8 . . . . -19.71(12) ?
C6 C5 C9 C8 . . . . 162.73(12) ?
C7 C8 C9 O2 . . . . 146.42(9) ?
Br1 C8 C9 O2 . . . . -88.19(10) ?
C7 C8 C9 C5 . . . . 30.26(11) ?
Br1 C8 C9 C5 . . . . 155.65(8) ?
C7 C8 C9 C10 . . . . -94.15(12) ?
Br1 C8 C9 C10 . . . . 31.24(13) ?
O2 C9 C10 C11 . . . . 22.67(12) ?
C5 C9 C10 C11 . . . . 143.00(10) ?
C8 C9 C10 C11 . . . . -99.18(12) ?
C9 C10 C11 C12 . . . . -22.29(12) ?
C9 O2 C12 O1 . . . . -179.74(11) ?
C9 O2 C12 C11 . . . . 0.15(13) ?
C10 C11 C12 O1 . . . . -165.58(13) ?
C10 C11 C12 O2 . . . . 14.53(13) ?


####################################################################### 
# 
# 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_dan9756
_database_code_depnum_ccdc_archive 'CCDC 2056210'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2021-01-14 deposited with the CCDC.	2021-04-23 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H11 Br O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         267.12

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   5.83760(10)
_cell_length_b                   9.7639(2)
_cell_length_c                   18.2223(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.1490(10)
_cell_angle_gamma                90
_cell_volume                     1035.91(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5606
_cell_measurement_theta_min      4.8666
_cell_measurement_theta_max      66.6165
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536

_exptl_absorpt_coefficient_mu    5.211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.42
_exptl_absorpt_correction_T_max  0.57

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Kappa CCD APEXII'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            8488
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_theta_min         4.87
_diffrn_reflns_theta_max         66.66
_diffrn_reflns_theta_full        66.66
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_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             1813
_reflns_number_gt                1746
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0242
_refine_ls_wR_factor_gt          0.0582
_refine_ls_wR_factor_ref         0.0589
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_restrained_S_all      1.126
_refine_ls_number_reflns         1813
_refine_ls_number_parameters     136
_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)+(0.0245P)²+1.0155P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.421
_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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'

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 0.99961(4) 0.60153(2) 0.65110(2) 0.01379(10) Uani d . . . 1 . .
O O1 1.0606(3) 0.29171(16) 0.81228(8) 0.0148(3) Uani d . . . 1 . .
O O2 0.8449(2) 0.31292(15) 0.70707(7) 0.0103(3) Uani d . . . 1 . .
C C1 0.2286(4) 0.1260(2) 0.59034(13) 0.0175(5) Uani d . . . 1 . .
H H1 0.1083 0.0657 0.6017 0.021 Uiso calc U . R 1 . .
C C2 0.3025(4) 0.1279(2) 0.51970(13) 0.0190(5) Uani d . . . 1 . .
H H2 0.2336 0.0679 0.4835 0.023 Uiso calc U . R 1 . .
C C3 0.4760(4) 0.2164(2) 0.50105(12) 0.0162(5) Uani d . . . 1 . .
H H3 0.525 0.218 0.4525 0.019 Uiso calc U . R 1 . .
C C4 0.5758(4) 0.3022(2) 0.55498(11) 0.0123(4) Uani d . . . 1 . .
C C5 0.5034(4) 0.2982(2) 0.62641(11) 0.0110(4) Uani d . . . 1 . .
C C6 0.3289(4) 0.2115(2) 0.64494(11) 0.0132(4) Uani d . . . 1 . .
H H6 0.279 0.2104 0.6934 0.016 Uiso calc U . R 1 . .
C C7 0.7640(4) 0.4079(2) 0.54971(12) 0.0142(5) Uani d . . . 1 . .
H H7A 0.7413 0.4629 0.5041 0.017 Uiso calc U . R 1 . .
H H7B 0.918 0.3649 0.5521 0.017 Uiso calc U . R 1 . .
C C8 0.7296(4) 0.4938(2) 0.61825(11) 0.0121(4) Uani d . . . 1 . .
H H8 0.6012 0.5593 0.6055 0.015 Uiso calc U . R 1 . .
C C9 0.6476(4) 0.3936(2) 0.67617(12) 0.0106(4) Uani d . . . 1 . .
C C10 0.5424(4) 0.4566(2) 0.74309(11) 0.0124(4) Uani d . . . 1 . .
H H10A 0.4972 0.553 0.7333 0.015 Uiso calc U . R 1 . .
H H10B 0.4056 0.4043 0.7558 0.015 Uiso calc U . R 1 . .
C C11 0.7325(4) 0.4480(2) 0.80482(11) 0.0135(4) Uani d . . . 1 . .
H H11A 0.8077 0.5381 0.8132 0.016 Uiso calc U . R 1 . .
H H11B 0.6705 0.4173 0.8512 0.016 Uiso calc U . R 1 . .
C C12 0.8994(4) 0.3446(2) 0.77845(11) 0.0108(4) 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 C8 . 1.953(2) ?
O1 C12 . 1.203(3) ?
O2 C12 . 1.352(2) ?
O2 C9 . 1.473(2) ?
C1 C2 . 1.387(3) ?
C1 C6 . 1.395(3) ?
C1 H1 . 0.95 ?
C2 C3 . 1.392(3) ?
C2 H2 . 0.95 ?
C3 C4 . 1.387(3) ?
C3 H3 . 0.95 ?
C4 C5 . 1.398(3) ?
C4 C7 . 1.515(3) ?
C5 C6 . 1.385(3) ?
C5 C9 . 1.512(3) ?
C6 H6 . 0.95 ?
C7 C8 . 1.530(3) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C9 . 1.541(3) ?
C8 H8 . 1.0 ?
C9 C10 . 1.533(3) ?
C10 C11 . 1.524(3) ?
C10 H10A . 0.99 ?
C10 H10B . 0.99 ?
C11 C12 . 1.505(3) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?

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
C12 O2 C9 . . 111.61(15) ?
C2 C1 C6 . . 120.7(2) ?
C2 C1 H1 . . 119.6 ?
C6 C1 H1 . . 119.6 ?
C1 C2 C3 . . 121.0(2) ?
C1 C2 H2 . . 119.5 ?
C3 C2 H2 . . 119.5 ?
C4 C3 C2 . . 118.5(2) ?
C4 C3 H3 . . 120.7 ?
C2 C3 H3 . . 120.7 ?
C3 C4 C5 . . 120.2(2) ?
C3 C4 C7 . . 129.45(19) ?
C5 C4 C7 . . 110.32(18) ?
C6 C5 C4 . . 121.41(19) ?
C6 C5 C9 . . 128.13(19) ?
C4 C5 C9 . . 110.40(19) ?
C5 C6 C1 . . 118.1(2) ?
C5 C6 H6 . . 121.0 ?
C1 C6 H6 . . 121.0 ?
C4 C7 C8 . . 100.55(17) ?
C4 C7 H7A . . 111.7 ?
C8 C7 H7A . . 111.7 ?
C4 C7 H7B . . 111.7 ?
C8 C7 H7B . . 111.7 ?
H7A C7 H7B . . 109.4 ?
C7 C8 C9 . . 106.05(17) ?
C7 C8 Br1 . . 113.26(15) ?
C9 C8 Br1 . . 114.58(14) ?
C7 C8 H8 . . 107.5 ?
C9 C8 H8 . . 107.5 ?
Br1 C8 H8 . . 107.5 ?
O2 C9 C5 . . 106.62(16) ?
O2 C9 C10 . . 104.93(16) ?
C5 C9 C10 . . 119.09(18) ?
O2 C9 C8 . . 109.19(17) ?
C5 C9 C8 . . 99.63(16) ?
C10 C9 C8 . . 116.87(17) ?
C11 C10 C9 . . 104.63(17) ?
C11 C10 H10A . . 110.8 ?
C9 C10 H10A . . 110.8 ?
C11 C10 H10B . . 110.8 ?
C9 C10 H10B . . 110.8 ?
H10A C10 H10B . . 108.9 ?
C12 C11 C10 . . 104.77(16) ?
C12 C11 H11A . . 110.8 ?
C10 C11 H11A . . 110.8 ?
C12 C11 H11B . . 110.8 ?
C10 C11 H11B . . 110.8 ?
H11A C11 H11B . . 108.9 ?
O1 C12 O2 . . 121.00(19) ?
O1 C12 C11 . . 128.64(19) ?
O2 C12 C11 . . 110.35(17) ?

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
C6 C1 C2 C3 . . . . -0.9(4) ?
C1 C2 C3 C4 . . . . 0.6(3) ?
C2 C3 C4 C5 . . . . 0.5(3) ?
C2 C3 C4 C7 . . . . -179.5(2) ?
C3 C4 C5 C6 . . . . -1.3(3) ?
C7 C4 C5 C6 . . . . 178.66(19) ?
C3 C4 C5 C9 . . . . 176.19(19) ?
C7 C4 C5 C9 . . . . -3.9(2) ?
C4 C5 C6 C1 . . . . 1.0(3) ?
C9 C5 C6 C1 . . . . -176.0(2) ?
C2 C1 C6 C5 . . . . 0.1(3) ?
C3 C4 C7 C8 . . . . 161.6(2) ?
C5 C4 C7 C8 . . . . -18.4(2) ?
C4 C7 C8 C9 . . . . 33.4(2) ?
C4 C7 C8 Br1 . . . . 159.87(14) ?
C12 O2 C9 C5 . . . . -141.21(17) ?
C12 O2 C9 C10 . . . . -14.0(2) ?
C12 O2 C9 C8 . . . . 112.02(18) ?
C6 C5 C9 O2 . . . . 87.9(3) ?
C4 C5 C9 O2 . . . . -89.4(2) ?
C6 C5 C9 C10 . . . . -30.4(3) ?
C4 C5 C9 C10 . . . . 152.33(18) ?
C6 C5 C9 C8 . . . . -158.7(2) ?
C4 C5 C9 C8 . . . . 24.1(2) ?
C7 C8 C9 O2 . . . . 76.2(2) ?
Br1 C8 C9 O2 . . . . -49.5(2) ?
C7 C8 C9 C5 . . . . -35.3(2) ?
Br1 C8 C9 C5 . . . . -161.03(14) ?
C7 C8 C9 C10 . . . . -165.03(18) ?
Br1 C8 C9 C10 . . . . 69.3(2) ?
O2 C9 C10 C11 . . . . 19.0(2) ?
C5 C9 C10 C11 . . . . 138.13(19) ?
C8 C9 C10 C11 . . . . -102.1(2) ?
C9 C10 C11 C12 . . . . -17.4(2) ?
C9 O2 C12 O1 . . . . -177.84(19) ?
C9 O2 C12 C11 . . . . 2.8(2) ?
C10 C11 C12 O1 . . . . -169.7(2) ?
C10 C11 C12 O2 . . . . 9.6(2) ?


####################################################################### 
# 
# 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_dan9942
_database_code_depnum_ccdc_archive 'CCDC 2056213'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2021-01-14 deposited with the CCDC.	2021-04-23 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2019.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H13 Br O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         281.14

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5352(2)
_cell_length_b                   8.6441(2)
_cell_length_c                   8.8394(2)
_cell_angle_alpha                77.5970(10)
_cell_angle_beta                 69.8180(10)
_cell_angle_gamma                67.0810(10)
_cell_volume                     561.35(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4344
_cell_measurement_theta_min      2.4656
_cell_measurement_theta_max      26.7563
_cell_measurement_temperature    102.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.168
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.057
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284

_exptl_absorpt_coefficient_mu    3.642
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 Bruker AXS area detector scaling and absorption correction.
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_T_max  0.82

_exptl_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.
;

_diffrn_ambient_temperature      102.(2)

_diffrn_source                   'Mo Ims'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON III Diffractometer'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            9047
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         26.77
_diffrn_reflns_theta_full        26.77
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

_refine_special_details          
;
;

_reflns_number_total             2386
_reflns_number_gt                2207
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0222
_refine_ls_wR_factor_gt          0.0482
_refine_ls_wR_factor_ref         0.0503
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_number_reflns         2386
_refine_ls_number_parameters     145
_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)+(0.0168P)²+0.3260P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.228
_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 0.0033 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'

_computing_data_collection       'APEX3 v2019.1-0'
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  ?

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 0.23935(3) 0.97392(2) 0.21046(2) 0.01792(7) Uani d . . . 1 . .
O O1 -0.09574(18) 0.67584(19) 0.35473(17) 0.0219(3) Uani d . . . 1 . .
O O2 0.19711(16) 0.60753(17) 0.24406(15) 0.0138(3) Uani d . . . 1 . .
C C1 0.4540(3) 0.2930(2) 0.3057(2) 0.0151(4) Uani d . . . 1 . .
H H1 0.333893 0.303354 0.362261 0.018 Uiso calc U . R 1 . .
C C2 0.5827(3) 0.1344(2) 0.2860(2) 0.0171(4) Uani d . . . 1 . .
H H2 0.550946 0.036683 0.330015 0.021 Uiso calc U . R 1 . .
C C3 0.7588(3) 0.1179(3) 0.2016(2) 0.0177(4) Uani d . . . 1 . .
H H3 0.847518 0.009294 0.186995 0.021 Uiso calc U . R 1 . .
C C4 0.8031(3) 0.2611(3) 0.1394(2) 0.0164(4) Uani d . . . 1 . .
H H4 0.923218 0.249419 0.081454 0.02 Uiso calc U . R 1 . .
C C5 0.6758(2) 0.4232(2) 0.1594(2) 0.0129(4) Uani d . . . 1 . .
C C6 0.4986(2) 0.4384(2) 0.2434(2) 0.0122(4) Uani d . . . 1 . .
C C7 0.7328(2) 0.5750(2) 0.0919(2) 0.0152(4) Uani d . . . 1 . .
H H7A 0.754803 0.590468 -0.026967 0.018 Uiso calc U . R 1 . .
H H7B 0.845847 0.554102 0.113805 0.018 Uiso calc U . R 1 . .
C C8 0.5943(2) 0.7365(2) 0.1642(2) 0.0143(4) Uani d . . . 1 . .
H H8A 0.593139 0.734736 0.276972 0.017 Uiso calc U . R 1 . .
H H8B 0.623527 0.835853 0.100389 0.017 Uiso calc U . R 1 . .
C C9 0.4137(2) 0.7470(2) 0.1611(2) 0.0129(4) Uani d . . . 1 . .
H H9 0.424514 0.729812 0.049073 0.015 Uiso calc U . R 1 . .
C C10 0.3526(2) 0.6099(2) 0.2775(2) 0.0120(4) Uani d . . . 1 . .
C C11 0.2869(2) 0.6390(2) 0.4596(2) 0.0142(4) Uani d . . . 1 . .
H H11A 0.328503 0.532061 0.525932 0.017 Uiso calc U . R 1 . .
H H11B 0.330827 0.721876 0.477926 0.017 Uiso calc U . R 1 . .
C C12 0.0843(2) 0.7067(3) 0.5020(2) 0.0164(4) Uani d . . . 1 . .
H H12A 0.031146 0.651097 0.606518 0.02 Uiso calc U . R 1 . .
H H12B 0.037115 0.830035 0.509187 0.02 Uiso calc U . R 1 . .
C C13 0.0452(3) 0.6652(2) 0.3658(2) 0.0154(4) 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 C9 . 1.9745(18) ?
O1 C13 . 1.207(2) ?
O2 C13 . 1.361(2) ?
O2 C10 . 1.464(2) ?
C1 C2 . 1.384(3) ?
C1 C6 . 1.399(3) ?
C1 H1 . 0.95 ?
C2 C3 . 1.394(3) ?
C2 H2 . 0.95 ?
C3 C4 . 1.380(3) ?
C3 H3 . 0.95 ?
C4 C5 . 1.401(3) ?
C4 H4 . 0.95 ?
C5 C6 . 1.403(3) ?
C5 C7 . 1.508(3) ?
C6 C10 . 1.528(3) ?
C7 C8 . 1.527(3) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C9 . 1.518(3) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C9 C10 . 1.524(3) ?
C9 H9 . 1.0 ?
C10 C11 . 1.552(2) ?
C11 C12 . 1.527(3) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 C13 . 1.499(3) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?

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
C13 O2 C10 . . 112.04(14) ?
C2 C1 C6 . . 120.79(18) ?
C2 C1 H1 . . 119.6 ?
C6 C1 H1 . . 119.6 ?
C1 C2 C3 . . 120.03(18) ?
C1 C2 H2 . . 120.0 ?
C3 C2 H2 . . 120.0 ?
C4 C3 C2 . . 119.32(18) ?
C4 C3 H3 . . 120.3 ?
C2 C3 H3 . . 120.3 ?
C3 C4 C5 . . 121.81(18) ?
C3 C4 H4 . . 119.1 ?
C5 C4 H4 . . 119.1 ?
C4 C5 C6 . . 118.42(17) ?
C4 C5 C7 . . 119.44(17) ?
C6 C5 C7 . . 122.14(17) ?
C1 C6 C5 . . 119.63(17) ?
C1 C6 C10 . . 118.34(16) ?
C5 C6 C10 . . 121.95(16) ?
C5 C7 C8 . . 112.69(15) ?
C5 C7 H7A . . 109.1 ?
C8 C7 H7A . . 109.1 ?
C5 C7 H7B . . 109.1 ?
C8 C7 H7B . . 109.1 ?
H7A C7 H7B . . 107.8 ?
C9 C8 C7 . . 108.26(15) ?
C9 C8 H8A . . 110.0 ?
C7 C8 H8A . . 110.0 ?
C9 C8 H8B . . 110.0 ?
C7 C8 H8B . . 110.0 ?
H8A C8 H8B . . 108.4 ?
C8 C9 C10 . . 111.41(15) ?
C8 C9 Br1 . . 109.68(12) ?
C10 C9 Br1 . . 111.32(12) ?
C8 C9 H9 . . 108.1 ?
C10 C9 H9 . . 108.1 ?
Br1 C9 H9 . . 108.1 ?
O2 C10 C9 . . 107.77(14) ?
O2 C10 C6 . . 107.44(14) ?
C9 C10 C6 . . 109.26(14) ?
O2 C10 C11 . . 104.42(14) ?
C9 C10 C11 . . 115.44(15) ?
C6 C10 C11 . . 112.03(15) ?
C12 C11 C10 . . 104.97(15) ?
C12 C11 H11A . . 110.8 ?
C10 C11 H11A . . 110.8 ?
C12 C11 H11B . . 110.8 ?
C10 C11 H11B . . 110.8 ?
H11A C11 H11B . . 108.8 ?
C13 C12 C11 . . 104.58(15) ?
C13 C12 H12A . . 110.8 ?
C11 C12 H12A . . 110.8 ?
C13 C12 H12B . . 110.8 ?
C11 C12 H12B . . 110.8 ?
H12A C12 H12B . . 108.9 ?
O1 C13 O2 . . 120.31(18) ?
O1 C13 C12 . . 128.93(18) ?
O2 C13 C12 . . 110.76(16) ?

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
C6 C1 C2 C3 . . . . -0.8(3) ?
C1 C2 C3 C4 . . . . 0.5(3) ?
C2 C3 C4 C5 . . . . 0.3(3) ?
C3 C4 C5 C6 . . . . -0.8(3) ?
C3 C4 C5 C7 . . . . 178.67(17) ?
C2 C1 C6 C5 . . . . 0.2(3) ?
C2 C1 C6 C10 . . . . -176.51(17) ?
C4 C5 C6 C1 . . . . 0.5(3) ?
C7 C5 C6 C1 . . . . -178.94(17) ?
C4 C5 C6 C10 . . . . 177.17(16) ?
C7 C5 C6 C10 . . . . -2.3(3) ?
C4 C5 C7 C8 . . . . -163.20(16) ?
C6 C5 C7 C8 . . . . 16.3(2) ?
C5 C7 C8 C9 . . . . -47.0(2) ?
C7 C8 C9 C10 . . . . 67.94(19) ?
C7 C8 C9 Br1 . . . . -168.34(12) ?
C13 O2 C10 C9 . . . . -110.31(16) ?
C13 O2 C10 C6 . . . . 132.06(15) ?
C13 O2 C10 C11 . . . . 12.93(19) ?
C8 C9 C10 O2 . . . . -168.95(14) ?
Br1 C9 C10 O2 . . . . 68.27(16) ?
C8 C9 C10 C6 . . . . -52.50(19) ?
Br1 C9 C10 C6 . . . . -175.28(12) ?
C8 C9 C10 C11 . . . . 74.8(2) ?
Br1 C9 C10 C11 . . . . -47.97(19) ?
C1 C6 C10 O2 . . . . -46.9(2) ?
C5 C6 C10 O2 . . . . 136.47(17) ?
C1 C6 C10 C9 . . . . -163.52(16) ?
C5 C6 C10 C9 . . . . 19.8(2) ?
C1 C6 C10 C11 . . . . 67.3(2) ?
C5 C6 C10 C11 . . . . -109.40(19) ?
O2 C10 C11 C12 . . . . -17.67(18) ?
C9 C10 C11 C12 . . . . 100.46(18) ?
C6 C10 C11 C12 . . . . -133.64(16) ?
C10 C11 C12 C13 . . . . 16.20(19) ?
C10 O2 C13 O1 . . . . 177.85(17) ?
C10 O2 C13 C12 . . . . -2.6(2) ?
C11 C12 C13 O1 . . . . 170.4(2) ?
C11 C12 C13 O2 . . . . -9.1(2) ?



#=============================================================================
#  end of cif data for "dan9942" (compound anti-5b)
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================

