# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_24dfbc
_database_code_depnum_ccdc_archive 'CCDC 1426052'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          284.5
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H3 Cl F2 O'
_chemical_formula_weight         176.54

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   3.8289(2)
_cell_length_b                   14.5220(6)
_cell_length_c                   12.2527(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.836(2)
_cell_angle_gamma                90
_cell_volume                     677.76(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    5852
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      30.53

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.529
_shelx_estimated_absorpt_T_min   0.857
_shelx_estimated_absorpt_T_max   0.857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6997
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_special_details           
;
in situ cryocrystallzation via OHCD
;
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8014
_diffrn_reflns_av_unetI/netI     0.0101
_diffrn_reflns_av_R_equivalents  0.0136
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.181
_diffrn_reflns_theta_max         30.530
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.688
_diffrn_measured_fraction_theta_full 0.761
_diffrn_reflns_Laue_measured_fraction_max 0.688
_diffrn_reflns_Laue_measured_fraction_full 0.761
_diffrn_reflns_point_group_measured_fraction_max 0.688
_diffrn_reflns_point_group_measured_fraction_full 0.761
_reflns_number_total             1435
_reflns_number_gt                1328
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR2014 (Burla et al., 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'PLATON (Spek, 2009) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'WINGX (Farrugia, 2014) and PLATON'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0372P)²+0.3106P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1435
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0763
_refine_ls_wR_factor_gt          0.0734
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.70003(13) 0.07566(2) 0.41842(3) 0.03109(16) Uani 1 1 d . . . . .
F1 F 0.5929(3) 0.29319(6) 0.14780(6) 0.0314(3) Uani 1 1 d . . . . .
F2 F 0.1562(3) 0.50459(5) 0.38566(8) 0.0328(3) Uani 1 1 d . . . . .
O1 O 0.8710(4) 0.13780(7) 0.23403(8) 0.0295(3) Uani 1 1 d . . . . .
C1 C 0.5709(4) 0.24943(8) 0.33361(9) 0.0167(4) Uani 1 1 d . . . . .
C2 C 0.5140(4) 0.31424(8) 0.24935(9) 0.0191(4) Uani 1 1 d . . . . .
C3 C 0.3748(5) 0.40017(9) 0.26470(10) 0.0231(4) Uani 1 1 d . . . . .
H3 H 0.3363 0.4430 0.2062 0.028 Uiso 1 1 calc R U . . .
C4 C 0.2936(5) 0.42114(8) 0.36928(11) 0.0213(4) Uani 1 1 d . . . . .
C5 C 0.3447(5) 0.36100(9) 0.45645(10) 0.0215(4) Uani 1 1 d . . . . .
H5 H 0.2880 0.3781 0.5274 0.026 Uiso 1 1 calc R U . . .
C6 C 0.4811(4) 0.27496(8) 0.43749(9) 0.0195(4) Uani 1 1 d . . . . .
H6 H 0.5147 0.2322 0.4963 0.023 Uiso 1 1 calc R U . . .
C7 C 0.7284(5) 0.15960(8) 0.31169(10) 0.0199(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C7 1.7990(13) . ?
F1 C2 1.3451(13) . ?
F2 C4 1.3442(15) . ?
O1 C7 1.1874(16) . ?
C1 C2 1.3976(16) . ?
C1 C6 1.4019(15) . ?
C1 C7 1.4731(18) . ?
C2 C3 1.3774(19) . ?
C3 C4 1.3829(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3781(18) . ?
C5 C6 1.3829(18) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 117.28(11) . . ?
C2 C1 C7 119.85(10) . . ?
C6 C1 C7 122.85(11) . . ?
F1 C2 C3 117.30(11) . . ?
F1 C2 C1 119.83(11) . . ?
C3 C2 C1 122.87(11) . . ?
C2 C3 C4 116.92(11) . . ?
C2 C3 H3 121.5 . . ?
C4 C3 H3 121.5 . . ?
F2 C4 C5 118.85(12) . . ?
F2 C4 C3 117.72(12) . . ?
C5 C4 C3 123.43(12) . . ?
C4 C5 C6 117.95(11) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C5 C6 C1 121.55(11) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
O1 C7 C1 127.75(12) . . ?
O1 C7 Cl1 117.95(10) . . ?
C1 C7 Cl1 114.30(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 F1 -179.49(14) . . . . ?
C7 C1 C2 F1 2.1(2) . . . . ?
C6 C1 C2 C3 -0.2(2) . . . . ?
C7 C1 C2 C3 -178.62(15) . . . . ?
F1 C2 C3 C4 179.83(15) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C2 C3 C4 F2 -179.76(15) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
F2 C4 C5 C6 178.99(15) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C1 1.0(2) . . . . ?
C2 C1 C6 C5 -0.6(2) . . . . ?
C7 C1 C6 C5 177.75(15) . . . . ?
C2 C1 C7 O1 13.3(3) . . . . ?
C6 C1 C7 O1 -164.96(17) . . . . ?
C2 C1 C7 Cl1 -167.58(12) . . . . ?
C6 C1 C7 Cl1 14.1(2) . . . . ?

_refine_diff_density_max         0.368
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.045



####################################################################### 
# 
# 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_25dfbc
_database_code_depnum_ccdc_archive 'CCDC 1426053'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          278.2
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H3 Cl F2 O'
_chemical_formula_weight         176.54

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4814(4)
_cell_length_b                   8.5648(4)
_cell_length_c                   10.7372(6)
_cell_angle_alpha                100.231(3)
_cell_angle_beta                 95.404(3)
_cell_angle_gamma                91.365(3)
_cell_volume                     673.48(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    9912
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      30.53

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.532
_shelx_estimated_absorpt_T_min   0.857
_shelx_estimated_absorpt_T_max   0.857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7107
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_special_details           
;
in situ cryocrystallzation via OHCD
;
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16476
_diffrn_reflns_av_unetI/netI     0.0103
_diffrn_reflns_av_R_equivalents  0.0166
_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
_diffrn_reflns_theta_min         1.937
_diffrn_reflns_theta_max         27.877
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.711
_diffrn_measured_fraction_theta_full 0.758
_diffrn_reflns_Laue_measured_fraction_max 0.711
_diffrn_reflns_Laue_measured_fraction_full 0.758
_diffrn_reflns_point_group_measured_fraction_max 0.711
_diffrn_reflns_point_group_measured_fraction_full 0.758
_reflns_number_total             2284
_reflns_number_gt                2093
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR2014 (Burla et al., 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'PLATON (Spek, 2009) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'WINGX (Farrugia, 2014) and PLATON'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0429P)²+0.6610P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2284
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0992
_refine_ls_wR_factor_gt          0.0964
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.13142(11) 0.43677(7) 0.86101(5) 0.0391(2) Uani 1 1 d . . . . .
F1 F 0.8418(2) 0.59832(14) 0.51842(11) 0.0286(4) Uani 1 1 d . . . . .
F2 F 1.1349(2) 1.04263(16) 0.91128(12) 0.0390(4) Uani 1 1 d . . . . .
O1 O 0.8860(3) 0.38599(18) 0.67245(15) 0.0375(5) Uani 1 1 d . . . . .
C2 C 0.9152(3) 0.7069(2) 0.61788(18) 0.0214(6) Uani 1 1 d . . . . .
C5 C 1.0607(4) 0.9307(2) 0.81345(19) 0.0268(6) Uani 1 1 d . . . . .
C1 C 0.9882(3) 0.6576(2) 0.72796(17) 0.0205(6) Uani 1 1 d . . . . .
C3 C 0.9144(3) 0.8635(2) 0.60429(18) 0.0230(6) Uani 1 1 d . . . . .
H3 H 0.8648 0.8921 0.5271 0.028 Uiso 1 1 calc R U . . .
C7 C 0.9811(4) 0.4872(3) 0.73772(19) 0.0269(6) Uani 1 1 d . . . . .
C6 C 1.0639(3) 0.7746(2) 0.82812(18) 0.0238(6) Uani 1 1 d . . . . .
H6 H 1.1166 0.7467 0.9047 0.029 Uiso 1 1 calc R U . . .
C4 C 0.9869(4) 0.9791(2) 0.7046(2) 0.0256(6) Uani 1 1 d . . . . .
H4 H 0.9858 1.0884 0.6986 0.031 Uiso 1 1 calc R U . . .
Cl1A Cl 0.37814(11) -0.23623(6) 0.12984(5) 0.0415(2) Uani 1 1 d . . . . .
F2A F 0.3520(2) 0.35171(16) 0.09780(13) 0.0373(4) Uani 1 1 d . . . . .
F1A F 0.6650(2) 0.08549(15) 0.47966(11) 0.0284(4) Uani 1 1 d . . . . .
O1A O 0.6022(3) -0.19547(19) 0.32995(15) 0.0382(5) Uani 1 1 d . . . . .
C1A C 0.5096(3) 0.0495(2) 0.27254(18) 0.0204(6) Uani 1 1 d . . . . .
C5A C 0.4323(4) 0.2843(3) 0.1918(2) 0.0253(6) Uani 1 1 d . . . . .
C4A C 0.5108(4) 0.3816(2) 0.3005(2) 0.0266(6) Uani 1 1 d . . . . .
H4A H 0.5118 0.4939 0.3083 0.032 Uiso 1 1 calc R U . . .
C2A C 0.5871(3) 0.1487(2) 0.38281(18) 0.0219(6) Uani 1 1 d . . . . .
C7A C 0.5170(4) -0.1252(2) 0.26164(18) 0.0270(6) Uani 1 1 d . . . . .
C3A C 0.5881(4) 0.3113(2) 0.3979(2) 0.0262(6) Uani 1 1 d . . . . .
H3A H 0.6415 0.3750 0.4745 0.031 Uiso 1 1 calc R U . . .
C6A C 0.4295(3) 0.1216(2) 0.17504(18) 0.0232(6) Uani 1 1 d . . . . .
H6A H 0.3742 0.0588 0.0986 0.028 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C7 1.774(2) . ?
F1 C2 1.349(2) . ?
F2 C5 1.356(2) . ?
O1 C7 1.187(3) . ?
C2 C3 1.375(3) . ?
C2 C1 1.393(3) . ?
C5 C6 1.374(3) . ?
C5 C4 1.380(3) . ?
C1 C6 1.399(3) . ?
C1 C7 1.482(3) . ?
C3 C4 1.386(3) . ?
C3 H3 0.9500 . ?
C6 H6 0.9500 . ?
C4 H4 0.9500 . ?
Cl1A C7A 1.784(2) . ?
F2A C5A 1.350(2) . ?
F1A C2A 1.347(2) . ?
O1A C7A 1.181(3) . ?
C1A C2A 1.396(3) . ?
C1A C6A 1.402(3) . ?
C1A C7A 1.483(3) . ?
C5A C6A 1.372(3) . ?
C5A C4A 1.380(3) . ?
C4A C3A 1.385(3) . ?
C4A H4A 0.9500 . ?
C2A C3A 1.372(3) . ?
C3A H3A 0.9500 . ?
C6A H6A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C2 C3 117.23(18) . . ?
F1 C2 C1 119.75(17) . . ?
C3 C2 C1 123.02(18) . . ?
F2 C5 C6 117.96(19) . . ?
F2 C5 C4 118.50(18) . . ?
C6 C5 C4 123.54(19) . . ?
C2 C1 C6 117.58(18) . . ?
C2 C1 C7 120.39(18) . . ?
C6 C1 C7 122.02(18) . . ?
C2 C3 C4 119.13(19) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
O1 C7 C1 126.3(2) . . ?
O1 C7 Cl1 119.12(17) . . ?
C1 C7 Cl1 114.60(16) . . ?
C5 C6 C1 118.68(19) . . ?
C5 C6 H6 120.7 . . ?
C1 C6 H6 120.7 . . ?
C5 C4 C3 118.03(19) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
C2A C1A C6A 117.62(18) . . ?
C2A C1A C7A 119.68(19) . . ?
C6A C1A C7A 122.69(18) . . ?
F2A C5A C6A 118.12(19) . . ?
F2A C5A C4A 118.67(19) . . ?
C6A C5A C4A 123.2(2) . . ?
C5A C4A C3A 118.19(19) . . ?
C5A C4A H4A 120.9 . . ?
C3A C4A H4A 120.9 . . ?
F1A C2A C3A 117.43(18) . . ?
F1A C2A C1A 119.98(18) . . ?
C3A C2A C1A 122.6(2) . . ?
O1A C7A C1A 127.2(2) . . ?
O1A C7A Cl1A 118.29(16) . . ?
C1A C7A Cl1A 114.46(17) . . ?
C2A C3A C4A 119.49(19) . . ?
C2A C3A H3A 120.3 . . ?
C4A C3A H3A 120.3 . . ?
C5A C6A C1A 118.90(19) . . ?
C5A C6A H6A 120.6 . . ?
C1A C6A H6A 120.6 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C2 C1 C6 179.5(2) . . . . ?
C3 C2 C1 C6 -0.1(4) . . . . ?
F1 C2 C1 C7 -1.7(4) . . . . ?
C3 C2 C1 C7 178.6(2) . . . . ?
F1 C2 C3 C4 179.4(2) . . . . ?
C1 C2 C3 C4 -0.9(4) . . . . ?
C2 C1 C7 O1 -17.3(4) . . . . ?
C6 C1 C7 O1 161.4(3) . . . . ?
C2 C1 C7 Cl1 163.0(2) . . . . ?
C6 C1 C7 Cl1 -18.3(3) . . . . ?
F2 C5 C6 C1 -179.9(2) . . . . ?
C4 C5 C6 C1 -0.2(4) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
C7 C1 C6 C5 -178.0(2) . . . . ?
F2 C5 C4 C3 178.8(2) . . . . ?
C6 C5 C4 C3 -0.9(4) . . . . ?
C2 C3 C4 C5 1.4(4) . . . . ?
F2A C5A C4A C3A 178.1(2) . . . . ?
C6A C5A C4A C3A -1.0(4) . . . . ?
C6A C1A C2A F1A 179.6(2) . . . . ?
C7A C1A C2A F1A -1.3(4) . . . . ?
C6A C1A C2A C3A -0.4(4) . . . . ?
C7A C1A C2A C3A 178.6(2) . . . . ?
C2A C1A C7A O1A -10.5(4) . . . . ?
C6A C1A C7A O1A 168.5(3) . . . . ?
C2A C1A C7A Cl1A 169.01(18) . . . . ?
C6A C1A C7A Cl1A -12.0(3) . . . . ?
F1A C2A C3A C4A 179.5(2) . . . . ?
C1A C2A C3A C4A -0.4(4) . . . . ?
C5A C4A C3A C2A 1.1(4) . . . . ?
F2A C5A C6A C1A -178.9(2) . . . . ?
C4A C5A C6A C1A 0.1(4) . . . . ?
C2A C1A C6A C5A 0.5(4) . . . . ?
C7A C1A C6A C5A -178.5(2) . . . . ?

_refine_diff_density_max         0.270
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.057



####################################################################### 
# 
# 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_26dfbc
_database_code_depnum_ccdc_archive 'CCDC 1426054'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          249.6
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H3 Cl F2 O'
_chemical_formula_weight         176.54

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.4388(2)
_cell_length_b                   15.7661(3)
_cell_length_c                   11.8282(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.5970(10)
_cell_angle_gamma                90
_cell_volume                     1384.49(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    9477
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      30.55

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.518
_shelx_estimated_absorpt_T_min   0.860
_shelx_estimated_absorpt_T_max   0.860
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7236
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_special_details           
;
in situ cryocrystallzation via OHCD
;
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44500
_diffrn_reflns_av_unetI/netI     0.0055
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.155
_diffrn_reflns_theta_max         28.275
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.776
_diffrn_measured_fraction_theta_full 0.828
_diffrn_reflns_Laue_measured_fraction_max 0.776
_diffrn_reflns_Laue_measured_fraction_full 0.828
_diffrn_reflns_point_group_measured_fraction_max 0.776
_diffrn_reflns_point_group_measured_fraction_full 0.828
_reflns_number_total             2661
_reflns_number_gt                2554
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR2014 (Burla et al., 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'PLATON (Spek, 2009) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'WINGX (Farrugia, 2014) and PLATON'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0294P)²+0.9261P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2661
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0262
_refine_ls_wR_factor_ref         0.0672
_refine_ls_wR_factor_gt          0.0658
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.36526(6) 0.41766(2) 0.90592(3) 0.03242(13) Uani 1 1 d . . . . .
Cl1A Cl 0.86089(6) 0.45992(2) 0.87722(3) 0.02888(12) Uani 1 1 d . . . . .
F2 F 0.64545(13) 0.29867(5) 1.00038(7) 0.0268(2) Uani 1 1 d . . . . .
F1 F 0.36479(13) 0.23269(6) 0.64380(7) 0.0281(2) Uani 1 1 d . . . . .
F1A F 0.81149(14) 0.52254(6) 0.52556(7) 0.0310(2) Uani 1 1 d . . . . .
F2A F 1.08297(15) 0.61249(6) 0.87425(7) 0.0361(3) Uani 1 1 d . . . . .
O1 O 0.4810(2) 0.39411(7) 0.70743(10) 0.0424(4) Uani 1 1 d . . . . .
O1A O 0.9689(2) 0.41350(6) 0.68456(10) 0.0441(4) Uani 1 1 d . . . . .
C7 C 0.4606(2) 0.36032(8) 0.79487(12) 0.0246(4) Uani 1 1 d . . . . .
C1 C 0.5015(2) 0.27015(8) 0.82137(11) 0.0176(3) Uani 1 1 d . . . . .
C2 C 0.4551(2) 0.20814(8) 0.74055(11) 0.0189(3) Uani 1 1 d . . . . .
C3 C 0.4909(2) 0.12350(8) 0.75695(12) 0.0215(3) Uani 1 1 d . . . . .
H3 H 0.4580 0.0831 0.6998 0.026 Uiso 1 1 calc R U . . .
C4 C 0.5766(2) 0.09831(8) 0.85927(12) 0.0225(3) Uani 1 1 d . . . . .
H4 H 0.6019 0.0399 0.8722 0.027 Uiso 1 1 calc R U . . .
C6 C 0.5884(2) 0.24146(8) 0.92206(11) 0.0182(3) Uani 1 1 d . . . . .
C5 C 0.6255(2) 0.15704(8) 0.94265(11) 0.0213(3) Uani 1 1 d . . . . .
H5 H 0.6835 0.1395 1.0126 0.026 Uiso 1 1 calc R U . . .
C7A C 0.9376(2) 0.47382(8) 0.73934(12) 0.0236(4) Uani 1 1 d . . . . .
C1A C 0.9473(2) 0.56319(8) 0.70166(11) 0.0170(3) Uani 1 1 d . . . . .
C2A C 0.8837(2) 0.58437(8) 0.59182(11) 0.0193(3) Uani 1 1 d . . . . .
C3A C 0.8848(2) 0.66593(9) 0.55061(12) 0.0255(4) Uani 1 1 d . . . . .
H3A H 0.8390 0.6783 0.4757 0.031 Uiso 1 1 calc R U . . .
C4A C 0.9546(2) 0.72956(9) 0.62123(14) 0.0288(4) Uani 1 1 d . . . . .
H4A H 0.9571 0.7862 0.5940 0.035 Uiso 1 1 calc R U . . .
C5A C 1.0206(2) 0.71201(9) 0.73080(14) 0.0274(4) Uani 1 1 d . . . . .
H5A H 1.0687 0.7559 0.7787 0.033 Uiso 1 1 calc R U . . .
C6A C 1.0153(2) 0.62976(9) 0.76873(11) 0.0217(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C7 1.7783(16) . ?
Cl1A C7A 1.7748(16) . ?
F2 C6 1.3426(14) . ?
F1 C2 1.3470(14) . ?
F1A C2A 1.3416(15) . ?
F2A C6A 1.3442(15) . ?
O1 C7 1.1817(18) . ?
O1A C7A 1.1822(18) . ?
C7 C1 1.4832(17) . ?
C1 C6 1.3945(17) . ?
C1 C2 1.3954(17) . ?
C2 C3 1.3723(18) . ?
C3 C4 1.3899(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.3848(19) . ?
C4 H4 0.9500 . ?
C6 C5 1.3778(18) . ?
C5 H5 0.9500 . ?
C7A C1A 1.4810(17) . ?
C1A C6A 1.3915(17) . ?
C1A C2A 1.3951(17) . ?
C2A C3A 1.3753(18) . ?
C3A C4A 1.385(2) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.385(2) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.374(2) . ?
C5A H5A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C7 C1 125.54(14) . . ?
O1 C7 Cl1 119.75(11) . . ?
C1 C7 Cl1 114.66(11) . . ?
C6 C1 C2 116.06(11) . . ?
C6 C1 C7 124.71(12) . . ?
C2 C1 C7 119.21(11) . . ?
F1 C2 C3 118.79(11) . . ?
F1 C2 C1 118.00(11) . . ?
C3 C2 C1 123.16(12) . . ?
C2 C3 C4 118.38(12) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C5 C4 C3 120.98(12) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
F2 C6 C5 118.42(11) . . ?
F2 C6 C1 118.74(11) . . ?
C5 C6 C1 122.78(12) . . ?
C6 C5 C4 118.63(12) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
O1A C7A C1A 125.84(14) . . ?
O1A C7A Cl1A 119.35(11) . . ?
C1A C7A Cl1A 114.74(10) . . ?
C6A C1A C2A 116.12(12) . . ?
C6A C1A C7A 124.67(12) . . ?
C2A C1A C7A 119.20(11) . . ?
F1A C2A C3A 118.92(12) . . ?
F1A C2A C1A 118.03(11) . . ?
C3A C2A C1A 122.99(12) . . ?
C2A C3A C4A 118.28(13) . . ?
C2A C3A H3A 120.9 . . ?
C4A C3A H3A 120.9 . . ?
C5A C4A C3A 121.14(13) . . ?
C5A C4A H4A 119.4 . . ?
C3A C4A H4A 119.4 . . ?
C6A C5A C4A 118.58(13) . . ?
C6A C5A H5A 120.7 . . ?
C4A C5A H5A 120.7 . . ?
F2A C6A C5A 118.53(12) . . ?
F2A C6A C1A 118.56(12) . . ?
C5A C6A C1A 122.88(13) . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C7 C1 C6 136.45(19) . . . . ?
Cl1 C7 C1 C6 -46.1(2) . . . . ?
O1 C7 C1 C2 -42.0(3) . . . . ?
Cl1 C7 C1 C2 135.49(13) . . . . ?
C6 C1 C2 F1 177.51(14) . . . . ?
C7 C1 C2 F1 -3.9(2) . . . . ?
C6 C1 C2 C3 0.1(2) . . . . ?
C7 C1 C2 C3 178.69(16) . . . . ?
F1 C2 C3 C4 -176.98(14) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C2 C1 C6 F2 176.27(14) . . . . ?
C7 C1 C6 F2 -2.2(2) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
C7 C1 C6 C5 -179.26(16) . . . . ?
F2 C6 C5 C4 -176.17(15) . . . . ?
C1 C6 C5 C4 0.9(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
O1A C7A C1A C6A -139.78(19) . . . . ?
Cl1A C7A C1A C6A 43.4(2) . . . . ?
O1A C7A C1A C2A 40.7(3) . . . . ?
Cl1A C7A C1A C2A -136.11(13) . . . . ?
C6A C1A C2A F1A -177.83(14) . . . . ?
C7A C1A C2A F1A 1.7(2) . . . . ?
C6A C1A C2A C3A -0.7(2) . . . . ?
C7A C1A C2A C3A 178.89(16) . . . . ?
F1A C2A C3A C4A 177.97(15) . . . . ?
C1A C2A C3A C4A 0.8(3) . . . . ?
C2A C3A C4A C5A -0.4(3) . . . . ?
C3A C4A C5A C6A -0.2(3) . . . . ?
C4A C5A C6A F2A 178.59(15) . . . . ?
C4A C5A C6A C1A 0.4(3) . . . . ?
C2A C1A C6A F2A -178.15(14) . . . . ?
C7A C1A C6A F2A 2.3(3) . . . . ?
C2A C1A C6A C5A 0.0(3) . . . . ?
C7A C1A C6A C5A -179.50(17) . . . . ?

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.048



####################################################################### 
# 
# 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_2fbc
_database_code_depnum_ccdc_archive 'CCDC 1440618'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          277.9
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H4 Cl F O'
_chemical_formula_weight         158.55

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   13.8205(6)
_cell_length_b                   12.5452(6)
_cell_length_c                   3.8197(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     662.26(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    2249
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      30.58

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.510
_shelx_estimated_absorpt_T_min   0.862
_shelx_estimated_absorpt_T_max   0.862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.858
_exptl_absorpt_correction_T_max  0.858
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_special_details           
;
in situ cryocrystallzation via OHCD
;
_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3137
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_limit_l_max       2
_diffrn_reflns_theta_min         2.192
_diffrn_reflns_theta_max         30.575
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.734
_diffrn_measured_fraction_theta_full 0.795
_diffrn_reflns_Laue_measured_fraction_max 0.734
_diffrn_reflns_Laue_measured_fraction_full 0.795
_diffrn_reflns_point_group_measured_fraction_max 0.647
_diffrn_reflns_point_group_measured_fraction_full 0.720
_reflns_number_total             1324
_reflns_number_gt                1236
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.554
_reflns_Friedel_fraction_max     0.533
_reflns_Friedel_fraction_full    0.617

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR2014 (Burla et al., 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'PLATON (Spek, 2009) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'WINGX (Farrugia, 2014) and PLATON'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0167P)²+0.2508P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 440 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1324
_refine_ls_number_parameters     91
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0268
_refine_ls_wR_factor_ref         0.0673
_refine_ls_wR_factor_gt          0.0601
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.58093(3) 0.92269(4) -0.3031(3) 0.0305(2) Uani 1 1 d . . . . .
F1 F 0.78863(12) 0.64734(11) -0.0707(6) 0.0382(5) Uani 1 1 d . . . . .
O1 O 0.62966(12) 0.72628(15) -0.3507(8) 0.0428(7) Uani 1 1 d . . . . .
C4 C 0.92995(14) 0.8672(2) 0.2456(13) 0.0273(8) Uani 1 1 d . . . . .
H4 H 0.9913 0.8797 0.3499 0.033 Uiso 1 1 calc R U . . .
C3 C 0.90250(14) 0.76393(19) 0.1636(11) 0.0264(7) Uani 1 1 d . . . . .
H3 H 0.9440 0.7055 0.2140 0.032 Uiso 1 1 calc R U . . .
C2 C 0.81400(16) 0.74780(18) 0.0078(9) 0.0224(7) Uani 1 1 d . . . . .
C1 C 0.75082(14) 0.83152(16) -0.0697(9) 0.0172(6) Uani 1 1 d . . . . .
C7 C 0.65765(14) 0.80917(18) -0.2436(9) 0.0232(8) Uani 1 1 d . . . . .
C5 C 0.86900(13) 0.95254(17) 0.1772(9) 0.0231(6) Uani 1 1 d . . . . .
H5 H 0.8880 1.0229 0.2388 0.028 Uiso 1 1 calc R U . . .
C6 C 0.78037(15) 0.93486(16) 0.0191(8) 0.0193(7) Uani 1 1 d . . . . .
H6 H 0.7390 0.9935 -0.0298 0.023 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C7 1.790(2) . ?
F1 C2 1.342(3) . ?
O1 C7 1.182(3) . ?
C4 C3 1.386(3) . ?
C4 C5 1.387(3) . ?
C4 H4 0.9500 . ?
C3 C2 1.375(3) . ?
C3 H3 0.9500 . ?
C2 C1 1.398(3) . ?
C1 C6 1.401(3) . ?
C1 C7 1.476(3) . ?
C5 C6 1.384(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C4 C5 120.9(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C2 C3 C4 118.6(2) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
F1 C2 C3 117.9(2) . . ?
F1 C2 C1 119.7(2) . . ?
C3 C2 C1 122.5(2) . . ?
C2 C1 C6 117.5(2) . . ?
C2 C1 C7 119.8(2) . . ?
C6 C1 C7 122.63(19) . . ?
O1 C7 C1 127.5(2) . . ?
O1 C7 Cl1 117.52(18) . . ?
C1 C7 Cl1 115.01(16) . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 120.80(19) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C4 C3 C2 1.0(6) . . . . ?
C4 C3 C2 F1 179.8(4) . . . . ?
C4 C3 C2 C1 -0.2(5) . . . . ?
F1 C2 C1 C6 179.7(3) . . . . ?
C3 C2 C1 C6 -0.3(5) . . . . ?
F1 C2 C1 C7 -1.3(4) . . . . ?
C3 C2 C1 C7 178.8(3) . . . . ?
C2 C1 C7 O1 -4.9(5) . . . . ?
C6 C1 C7 O1 174.1(3) . . . . ?
C2 C1 C7 Cl1 176.4(2) . . . . ?
C6 C1 C7 Cl1 -4.5(4) . . . . ?
C3 C4 C5 C6 -1.2(6) . . . . ?
C4 C5 C6 C1 0.7(5) . . . . ?
C2 C1 C6 C5 0.1(5) . . . . ?
C7 C1 C6 C5 -179.0(3) . . . . ?

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.055



####################################################################### 
# 
# 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_bc
_database_code_depnum_ccdc_archive 'CCDC 1440619'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          273.5
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H5 Cl O'
_chemical_formula_weight         140.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.4704(5)
_cell_length_b                   3.9581(2)
_cell_length_c                   22.3439(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.566(3)
_cell_angle_gamma                90
_cell_volume                     659.40(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4203
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      30.39

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   0.856
_exptl_transmission_factor_max   0.856
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.482
_shelx_estimated_absorpt_T_min   0.869
_shelx_estimated_absorpt_T_max   0.869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_special_details           
;
in situ cryocrystallzation via OHCD
;
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7678
_diffrn_reflns_av_unetI/netI     0.0105
_diffrn_reflns_av_R_equivalents  0.0126
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.826
_diffrn_reflns_theta_max         28.695
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measured_fraction_theta_full 0.936
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_Laue_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_point_group_measured_fraction_full 0.936
_reflns_number_total             1555
_reflns_number_gt                1398
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR2014 (Burla et al., 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'PLATON (Spek, 2009) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'WINGX (Farrugia, 2014) and PLATON'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0691P)²+0.4288P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1555
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1544
_refine_ls_wR_factor_gt          0.1507
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      1.112
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.17545(9) 0.48504(19) 0.44790(3) 0.0662(3) Uani 1 1 d . . . . .
O1 O 0.1158(2) 0.4075(7) 0.33536(10) 0.0746(7) Uani 1 1 d . . . . .
C7 C 0.2265(3) 0.3579(6) 0.37415(10) 0.0434(5) Uani 1 1 d . . . . .
C1 C 0.4033(2) 0.2018(5) 0.36839(9) 0.0348(4) Uani 1 1 d . . . . .
C2 C 0.4396(3) 0.0884(6) 0.31189(10) 0.0408(5) Uani 1 1 d . . . . .
H2 H 0.3518 0.1112 0.2795 0.049 Uiso 1 1 calc R U . . .
C3 C 0.6037(3) -0.0582(6) 0.30239(12) 0.0507(6) Uani 1 1 d . . . . .
H3 H 0.6287 -0.1360 0.2636 0.061 Uiso 1 1 calc R U . . .
C4 C 0.7303(3) -0.0909(6) 0.34936(13) 0.0555(7) Uani 1 1 d . . . . .
H4 H 0.8427 -0.1925 0.3430 0.067 Uiso 1 1 calc R U . . .
C6 C 0.5316(3) 0.1676(6) 0.41576(11) 0.0460(5) Uani 1 1 d . . . . .
H6 H 0.5070 0.2431 0.4548 0.055 Uiso 1 1 calc R U . . .
C5 C 0.6950(3) 0.0231(7) 0.40567(14) 0.0581(7) Uani 1 1 d . . . . .
H5 H 0.7838 0.0020 0.4378 0.070 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C7 1.787(2) . ?
O1 C7 1.177(3) . ?
C7 C1 1.471(3) . ?
C1 C2 1.383(3) . ?
C1 C6 1.389(3) . ?
C2 C3 1.385(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.378(4) . ?
C4 H4 0.9500 . ?
C6 C5 1.379(3) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C7 C1 126.8(2) . . ?
O1 C7 Cl1 116.85(18) . . ?
C1 C7 Cl1 116.32(15) . . ?
C2 C1 C6 119.94(19) . . ?
C2 C1 C7 116.37(17) . . ?
C6 C1 C7 123.69(19) . . ?
C1 C2 C3 120.1(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C5 C6 C1 119.4(2) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C7 C1 C2 -3.1(4) . . . . ?
Cl1 C7 C1 C2 176.96(16) . . . . ?
O1 C7 C1 C6 176.4(3) . . . . ?
Cl1 C7 C1 C6 -3.6(3) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?
C7 C1 C2 C3 179.3(2) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C7 C1 C6 C5 -178.8(2) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C1 C6 C5 C4 -0.9(4) . . . . ?

_refine_diff_density_max         0.328
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.051



####################################################################### 
# 
# 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_23dfbc
_database_code_depnum_ccdc_archive 'CCDC 1452040'
_audit_update_record             
;
2016-04-14 deposited with the CCDC.
2016-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          262.5
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H3 Cl F2 O'
_chemical_formula_weight         176.54

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.85900(10)
_cell_length_b                   7.20060(10)
_cell_length_c                   8.03650(10)
_cell_angle_alpha                94.6130(10)
_cell_angle_beta                 104.2750(10)
_cell_angle_gamma                115.9060(10)
_cell_volume                     337.849(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    6234
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      30.53

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_F_000             176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.530
_shelx_estimated_absorpt_T_min   0.857
_shelx_estimated_absorpt_T_max   0.857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.853
_exptl_absorpt_correction_T_max  0.853
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_special_details           
;
in situ cryocrystallzation via OHCD
;
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6690
_diffrn_reflns_av_unetI/netI     0.0059
_diffrn_reflns_av_R_equivalents  0.0093
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.678
_diffrn_reflns_theta_max         28.273
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.721
_diffrn_measured_fraction_theta_full 0.785
_diffrn_reflns_Laue_measured_fraction_max 0.721
_diffrn_reflns_Laue_measured_fraction_full 0.785
_diffrn_reflns_point_group_measured_fraction_max 0.721
_diffrn_reflns_point_group_measured_fraction_full 0.785
_reflns_number_total             1210
_reflns_number_gt                1190
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR2014 (Burla et al., 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'PLATON (Spek, 2009) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'WINGX (Farrugia, 2014) and PLATON'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0351P)²+0.1592P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1210
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0726
_refine_ls_wR_factor_gt          0.0723
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_restrained_S_all      1.158
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.68906(7) 0.77056(8) 0.93339(4) 0.03450(18) Uani 1 1 d . . . . .
F2 F -0.14086(16) 0.78161(17) 0.37637(11) 0.0258(3) Uani 1 1 d . . . . .
F1 F 0.02139(16) 0.79670(16) 0.71317(11) 0.0239(3) Uani 1 1 d . . . . .
O1 O 0.3104(2) 0.7355(2) 0.96205(14) 0.0347(4) Uani 1 1 d . . . . .
C1 C 0.3324(3) 0.7513(3) 0.67157(15) 0.0151(4) Uani 1 1 d . . . . .
C3 C 0.0521(3) 0.7649(3) 0.43122(17) 0.0173(4) Uani 1 1 d . . . . .
C4 C 0.1579(3) 0.7385(3) 0.31362(16) 0.0185(4) Uani 1 1 d . . . . .
H4 H 0.0980 0.7338 0.1925 0.022 Uiso 1 1 calc R U . . .
C6 C 0.4419(3) 0.7262(3) 0.55236(16) 0.0164(4) Uani 1 1 d . . . . .
H6 H 0.5773 0.7142 0.5931 0.020 Uiso 1 1 calc R U . . .
C5 C 0.3548(3) 0.7188(3) 0.37554(16) 0.0181(4) Uani 1 1 d . . . . .
H5 H 0.4299 0.7001 0.2960 0.022 Uiso 1 1 calc R U . . .
C2 C 0.1359(3) 0.7716(3) 0.60806(16) 0.0157(4) Uani 1 1 d . . . . .
C7 C 0.4118(3) 0.7497(3) 0.86031(17) 0.0200(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C7 1.7805(15) . ?
F2 C3 1.3494(14) . ?
F1 C2 1.3375(14) . ?
O1 C7 1.1807(18) . ?
C1 C2 1.3942(17) . ?
C1 C6 1.4002(18) . ?
C1 C7 1.4826(17) . ?
C3 C4 1.3732(19) . ?
C3 C2 1.3835(18) . ?
C4 C5 1.3921(18) . ?
C4 H4 0.9500 . ?
C6 C5 1.3857(17) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.26(11) . . ?
C2 C1 C7 118.84(12) . . ?
C6 C1 C7 122.86(12) . . ?
F2 C3 C4 120.56(12) . . ?
F2 C3 C2 117.73(12) . . ?
C4 C3 C2 121.70(12) . . ?
C3 C4 C5 118.63(12) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C5 C6 C1 120.68(12) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C6 C5 C4 120.51(12) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
F1 C2 C3 117.74(11) . . ?
F1 C2 C1 122.05(11) . . ?
C3 C2 C1 120.22(12) . . ?
O1 C7 C1 126.73(13) . . ?
O1 C7 Cl1 118.86(10) . . ?
C1 C7 Cl1 114.40(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F2 C3 C4 C5 -179.05(15) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C2 C1 C6 C5 -0.9(3) . . . . ?
C7 C1 C6 C5 176.91(15) . . . . ?
C1 C6 C5 C4 0.7(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
F2 C3 C2 F1 -0.8(2) . . . . ?
C4 C3 C2 F1 -179.65(16) . . . . ?
F2 C3 C2 C1 178.84(15) . . . . ?
C4 C3 C2 C1 -0.1(3) . . . . ?
C6 C1 C2 F1 -179.81(15) . . . . ?
C7 C1 C2 F1 2.2(2) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C7 C1 C2 C3 -177.33(15) . . . . ?
C2 C1 C7 O1 11.0(3) . . . . ?
C6 C1 C7 O1 -166.86(18) . . . . ?
C2 C1 C7 Cl1 -169.32(13) . . . . ?
C6 C1 C7 Cl1 12.8(2) . . . . ?

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.056



