 
data_C17H16BrFO3
 
_audit_creation_method            'SHELXL-2016/6'
_shelx_SHELXL_version_number      '2016/6'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C17 H16 Br F O3'
_chemical_formula_sum
 'C17 H16 Br F O3' 
_chemical_formula_weight          367.21

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0181   0.0091
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Br'  'Br'  -0.6763   1.2805
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'F'  'F'   0.0727   0.0534
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0492   0.0322
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       orthorhombic
_space_group_IT_number            19
_space_group_name_H-M_alt         'P 21 21 21'
_space_group_name_Hall            'P 2ac 2ab'
 
_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, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    5.7046(3)
_cell_length_b                    7.4441(4)
_cell_length_c                    35.724(2)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1517.06(14)
_cell_formula_units_Z             4
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     9914
_cell_measurement_theta_min       2.47
_cell_measurement_theta_max       69.84
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       'not measured' 
_exptl_crystal_density_method     none
_exptl_crystal_density_diffrn     1.608          
_exptl_crystal_F_000              744
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.440
_exptl_crystal_size_mid           0.340
_exptl_crystal_size_min           0.080
_exptl_absorpt_coefficient_mu     3.889
_shelx_estimated_absorpt_T_min    0.279
_shelx_estimated_absorpt_T_max    0.746
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.5277
_exptl_absorpt_correction_T_max   0.7533
_exptl_absorpt_process_details
;
Sheldrick, G.M. (2016). SADABS. Bruker AXS Inc. Madison, WI USA.
;
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      1.54178
_diffrn_radiation_type            CuK\a
_diffrn_source                    'microfocus sealed tube'
_diffrn_source_type               'Incoatec I\uS'
_diffrn_radiation_monochromator   mirrors 
_diffrn_measurement_device_type   'Bruker Kappa DUO CCD diffractometer'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             16996
_diffrn_reflns_av_unetI/netI      0.0280
_diffrn_reflns_av_R_equivalents   0.0471
_diffrn_reflns_limit_h_min        -6
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_k_max        8
_diffrn_reflns_limit_l_min        -43
_diffrn_reflns_limit_l_max        42
_diffrn_reflns_theta_min          2.474
_diffrn_reflns_theta_max          69.834
_diffrn_reflns_theta_full         67.679
_diffrn_measured_fraction_theta_max   0.993
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.993
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.992
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              2841
_reflns_number_gt                 2833
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.670
_reflns_Friedel_fraction_max      0.991
_reflns_Friedel_fraction_full     0.998
 
_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        'APEX2 (Bruker, 2014)'
_computing_cell_refinement        'SAINT (Bruker, 2014)'
_computing_data_reduction         'SAINT (Bruker, 2014)'
_computing_structure_solution     'SHELXT 2016/6 (Sheldrick, 2016)'
_computing_structure_refinement   'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'
_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)+(0.0237P)²+4.5260P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      dual
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
 Flack x determined using 1101 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    -0.008(14)
_chemical_absolute_configuration  ad
_refine_ls_number_reflns          2841
_refine_ls_number_parameters      203
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.0445
_refine_ls_R_factor_gt            0.0444
_refine_ls_wR_factor_ref          0.1144
_refine_ls_wR_factor_gt           0.1143
_refine_ls_goodness_of_fit_ref    1.300
_refine_ls_restrained_S_all       1.300
_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
Br1 Br 1.05900(15) 1.06393(10) 0.25551(2) 0.0342(2) Uani 1 1 d . . . . .
F1 F 0.4998(8) 0.1606(5) 0.48480(10) 0.0342(11) Uani 1 1 d . . . . .
O1 O 0.8253(10) 0.3426(8) 0.44136(13) 0.0321(11) Uani 1 1 d D . . . .
H1O H 0.845(14) 0.318(11) 0.4640(9) 0.03(2) Uiso 1 1 d D . . . .
O2 O 0.7070(9) 0.7564(6) 0.42558(13) 0.0276(11) Uani 1 1 d . . . . .
O3 O 1.0610(11) 0.8587(7) 0.44263(12) 0.0347(11) Uani 1 1 d . . . . .
C1 C 0.7027(12) 0.3548(9) 0.36880(19) 0.0231(13) Uani 1 1 d . . . . .
H1 H 0.845268 0.302607 0.377210 0.028 Uiso 1 1 calc R U . . .
C2 C 0.6663(13) 0.3781(8) 0.33089(19) 0.0237(14) Uani 1 1 d . . . . .
H2 H 0.783030 0.341669 0.313509 0.028 Uiso 1 1 calc R U . . .
C3 C 0.4583(13) 0.4553(8) 0.31811(16) 0.0234(13) Uani 1 1 d . . . . .
H3 H 0.434095 0.474626 0.292113 0.028 Uiso 1 1 calc R U . . .
C4 C 0.2887(12) 0.5029(9) 0.34359(19) 0.0244(14) Uani 1 1 d . . . . .
H4 H 0.145150 0.552856 0.335000 0.029 Uiso 1 1 calc R U . . .
C5 C 0.3245(12) 0.4789(8) 0.38178(18) 0.0219(13) Uani 1 1 d . . . . .
H5 H 0.205409 0.512216 0.399023 0.026 Uiso 1 1 calc R U . . .
C6 C 0.5346(13) 0.4061(8) 0.39493(16) 0.0225(13) Uani 1 1 d . . . . .
C7 C 0.5811(13) 0.3762(9) 0.43669(17) 0.0234(13) Uani 1 1 d . . . . .
C8 C 0.5006(11) 0.5337(9) 0.46163(17) 0.0250(15) Uani 1 1 d . . . . .
H8A H 0.348150 0.578403 0.452196 0.030 Uiso 1 1 calc R U . . .
H8B H 0.475220 0.488345 0.487361 0.030 Uiso 1 1 calc R U . . .
C9 C 0.6696(16) 0.6880(10) 0.46321(18) 0.0339(18) Uani 1 1 d . . . . .
H9A H 0.605721 0.784375 0.479364 0.041 Uiso 1 1 calc R U . . .
H9B H 0.820432 0.647491 0.474009 0.041 Uiso 1 1 calc R U . . .
C10 C 0.9133(13) 0.8338(8) 0.41905(17) 0.0241(14) Uani 1 1 d . . . . .
C11 C 0.9406(13) 0.8842(8) 0.37875(16) 0.0213(12) Uani 1 1 d . . . . .
C12 C 1.1489(13) 0.9701(9) 0.36829(19) 0.0281(15) Uani 1 1 d . . . . .
H12 H 1.266474 0.993108 0.386510 0.034 Uiso 1 1 calc R U . . .
C13 C 1.1839(12) 1.0213(8) 0.33167(19) 0.0253(14) Uani 1 1 d . . . . .
H13 H 1.324310 1.080691 0.324471 0.030 Uiso 1 1 calc R U . . .
C14 C 1.0121(12) 0.9851(8) 0.30568(16) 0.0232(15) Uani 1 1 d . . . . .
C15 C 0.8054(12) 0.8973(8) 0.31514(18) 0.0212(13) Uani 1 1 d . . . . .
H15 H 0.688978 0.873326 0.296791 0.025 Uiso 1 1 calc R U . . .
C16 C 0.7738(11) 0.8459(9) 0.35192(18) 0.0208(13) Uani 1 1 d . . . . .
H16 H 0.635398 0.783230 0.358869 0.025 Uiso 1 1 calc R U . . .
C17 C 0.4486(15) 0.2060(9) 0.44716(17) 0.0290(15) Uani 1 1 d . . . . .
H17A H 0.277936 0.225636 0.444198 0.035 Uiso 1 1 calc R U . . .
H17B H 0.495816 0.106486 0.430397 0.035 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
Br1 C14 1.905(6) . ?
F1 C17 1.417(7) . ?
O1 C7 1.425(9) . ?
O1 H1O 0.84(3) . ?
O2 C10 1.331(9) . ?
O2 C9 1.453(8) . ?
O3 C10 1.206(9) . ?
C1 C2 1.381(9) . ?
C1 C6 1.392(9) . ?
C1 H1 0.9500 . ?
C2 C3 1.395(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.396(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.532(8) . ?
C7 C17 1.522(10) . ?
C7 C8 1.543(9) . ?
C8 C9 1.501(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.496(8) . ?
C11 C16 1.380(9) . ?
C11 C12 1.400(10) . ?
C12 C13 1.377(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(10) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(9) . ?
C15 C16 1.380(9) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
 
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
C7 O1 H1O 107(6) . . ?
C10 O2 C9 116.3(6) . . ?
C2 C1 C6 121.3(6) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
C1 C2 C3 120.0(6) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 119.2(6) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.8(6) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 120.4(6) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.2(6) . . ?
C1 C6 C7 119.6(6) . . ?
C5 C6 C7 122.2(6) . . ?
O1 C7 C17 108.1(6) . . ?
O1 C7 C6 108.0(5) . . ?
C17 C7 C6 105.9(5) . . ?
O1 C7 C8 110.9(6) . . ?
C17 C7 C8 110.1(5) . . ?
C6 C7 C8 113.6(5) . . ?
C9 C8 C7 114.3(6) . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
O2 C9 C8 109.1(5) . . ?
O2 C9 H9A 109.9 . . ?
C8 C9 H9A 109.9 . . ?
O2 C9 H9B 109.9 . . ?
C8 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
O3 C10 O2 124.2(6) . . ?
O3 C10 C11 124.1(7) . . ?
O2 C10 C11 111.7(6) . . ?
C16 C11 C12 119.6(6) . . ?
C16 C11 C10 123.0(6) . . ?
C12 C11 C10 117.4(6) . . ?
C13 C12 C11 120.2(6) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C14 C13 C12 118.9(6) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C13 C14 C15 122.1(6) . . ?
C13 C14 Br1 118.3(5) . . ?
C15 C14 Br1 119.5(5) . . ?
C16 C15 C14 118.2(6) . . ?
C16 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
C11 C16 C15 120.9(6) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
F1 C17 C7 109.2(6) . . ?
F1 C17 H17A 109.8 . . ?
C7 C17 H17A 109.8 . . ?
F1 C17 H17B 109.8 . . ?
C7 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
 
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 C3 0.3(10) . . . . ?
C1 C2 C3 C4 -1.7(9) . . . . ?
C2 C3 C4 C5 1.5(10) . . . . ?
C3 C4 C5 C6 0.2(10) . . . . ?
C2 C1 C6 C5 1.3(10) . . . . ?
C2 C1 C6 C7 179.5(6) . . . . ?
C4 C5 C6 C1 -1.6(9) . . . . ?
C4 C5 C6 C7 -179.6(6) . . . . ?
C1 C6 C7 O1 15.7(8) . . . . ?
C5 C6 C7 O1 -166.2(6) . . . . ?
C1 C6 C7 C17 -99.9(7) . . . . ?
C5 C6 C7 C17 78.2(7) . . . . ?
C1 C6 C7 C8 139.2(6) . . . . ?
C5 C6 C7 C8 -42.7(9) . . . . ?
O1 C7 C8 C9 40.7(8) . . . . ?
C17 C7 C8 C9 160.3(6) . . . . ?
C6 C7 C8 C9 -81.2(8) . . . . ?
C10 O2 C9 C8 -152.0(6) . . . . ?
C7 C8 C9 O2 58.7(8) . . . . ?
C9 O2 C10 O3 -4.3(10) . . . . ?
C9 O2 C10 C11 174.9(5) . . . . ?
O3 C10 C11 C16 176.5(7) . . . . ?
O2 C10 C11 C16 -2.8(9) . . . . ?
O3 C10 C11 C12 -1.9(9) . . . . ?
O2 C10 C11 C12 178.8(6) . . . . ?
C16 C11 C12 C13 2.1(10) . . . . ?
C10 C11 C12 C13 -179.4(6) . . . . ?
C11 C12 C13 C14 -0.6(10) . . . . ?
C12 C13 C14 C15 -0.5(10) . . . . ?
C12 C13 C14 Br1 178.0(5) . . . . ?
C13 C14 C15 C16 0.1(9) . . . . ?
Br1 C14 C15 C16 -178.4(5) . . . . ?
C12 C11 C16 C15 -2.5(9) . . . . ?
C10 C11 C16 C15 179.1(6) . . . . ?
C14 C15 C16 C11 1.4(9) . . . . ?
O1 C7 C17 F1 59.4(7) . . . . ?
C6 C7 C17 F1 174.9(6) . . . . ?
C8 C7 C17 F1 -61.9(7) . . . . ?

loop_
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
O1 H1O F1  0.84(3) 2.04(4) 2.819(6) 155(8) 4_556
 
_refine_diff_density_max    0.907
_refine_diff_density_min   -0.774
_refine_diff_density_rms    0.105



