# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_c2_c
_database_code_depnum_ccdc_archive 'CCDC 1837087'
_audit_update_record             
;
2018-04-15 deposited with the CCDC.
2018-12-07 downloaded from the CCDC.
;
_audit_creation_date             2018-04-15
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2015.06.08 svn.r3188 for OlexSys, GUI svn.r5047)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H15 F3 O4'
_chemical_formula_sum            'C19 H15 F3 O4'
_chemical_formula_weight         364.31
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.470(2)
_cell_length_b                   9.9387(6)
_cell_length_c                   17.2934(12)
_cell_angle_alpha                90
_cell_angle_beta                 123.484(7)
_cell_angle_gamma                90
_cell_volume                     3364.5(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2947
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.994
_cell_measurement_theta_min      2.081
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12087
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.081
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2393
_reflns_number_total             2947
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         2947
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.130
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0901P)²+0.0577P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1456
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C16(H16), C20(H20), C24(H24)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.14868(6) 0.48288(11) 0.29308(7) 0.0405(4) Uani 1 1 d . . . . .
O2 O 0.03043(7) -0.10814(11) 0.13427(9) 0.0306(4) Uani 1 1 d . . . . .
O3 O 0.22359(7) 0.38385(13) 0.20336(11) 0.0413(4) Uani 1 1 d . . . . .
O4 O 0.18394(7) 0.97640(13) -0.09509(9) 0.0355(4) Uani 1 1 d . . . . .
F5 F 0.05759(7) 0.59752(15) 0.24253(9) 0.0573(4) Uani 1 1 d . . . . .
F6 F 0.15280(8) 0.69709(12) 0.29817(8) 0.0579(4) Uani 1 1 d . . . . .
C7 C 0.12422(9) 0.25305(16) 0.15007(11) 0.0213(4) Uani 1 1 d . . . . .
O8 O 0.07234(9) 0.43596(14) -0.03750(10) 0.0524(5) Uani 1 1 d . . . . .
C9 C 0.12835(9) 0.01463(17) 0.17772(12) 0.0253(4) Uani 1 1 d . . . . .
H9 H 0.1533 -0.0646 0.2010 0.030 Uiso 1 1 calc R . . . .
C10 C 0.17427(9) 0.73760(18) 0.05904(12) 0.0255(4) Uani 1 1 d . . . . .
H10 H 0.1924 0.7230 0.1216 0.031 Uiso 1 1 calc R . . . .
C11 C 0.02022(9) 0.13116(16) 0.09992(12) 0.0236(4) Uani 1 1 d . . . . .
H11 H -0.0269 0.1305 0.0712 0.028 Uiso 1 1 calc R . . . .
C12 C 0.05397(9) 0.24969(16) 0.10742(12) 0.0236(4) Uani 1 1 d . . . . .
H12 H 0.0290 0.3287 0.0833 0.028 Uiso 1 1 calc R . . . .
C13 C 0.05779(9) 0.01318(16) 0.13589(12) 0.0230(4) Uani 1 1 d . . . . .
C14 C 0.16089(9) 0.13238(17) 0.18460(12) 0.0242(4) Uani 1 1 d . . . . .
H14 H 0.2080 0.1326 0.2125 0.029 Uiso 1 1 calc R . . . .
C15 C 0.10463(10) 0.52470(17) 0.01829(13) 0.0285(4) Uani 1 1 d . . . . .
C16 C 0.10091(10) 0.67074(18) -0.09996(12) 0.0266(4) Uani 1 1 d . . . . .
H16 H 0.0695 0.6108 -0.1445 0.032 Uiso 1 1 calc R . . . .
C17 C 0.12704(9) 0.64708(16) -0.00625(12) 0.0231(4) Uani 1 1 d . . . . .
C18 C 0.16798(10) 0.87070(17) -0.06095(13) 0.0259(4) Uani 1 1 d . . . . .
C19 C 0.12243(9) 0.50706(17) 0.11583(12) 0.0231(4) Uani 1 1 d . . . . .
C20 C 0.19477(10) 0.84929(17) 0.03233(13) 0.0268(4) Uani 1 1 d . . . . .
H20 H 0.2262 0.9094 0.0766 0.032 Uiso 1 1 calc R . . . .
C21 C 0.16185(9) 0.37835(17) 0.16183(12) 0.0255(4) Uani 1 1 d . . . . .
C22 C 0.10372(10) 0.60030(17) 0.15256(13) 0.0248(4) Uani 1 1 d . . . . .
C23 C 0.23112(11) 1.07369(19) -0.03119(15) 0.0384(5) Uani 1 1 d . . . . .
H23A H 0.2396 1.1401 -0.0640 0.058 Uiso 1 1 calc GR . . . .
H23B H 0.2732 1.0300 0.0138 0.058 Uiso 1 1 calc GR . . . .
H23C H 0.2123 1.1165 -0.0003 0.058 Uiso 1 1 calc GR . . . .
C24 C 0.12081(10) 0.78048(18) -0.12699(12) 0.0290(5) Uani 1 1 d . . . . .
H24 H 0.1029 0.7949 -0.1895 0.035 Uiso 1 1 calc R . . . .
C25 C -0.04026(10) -0.11314(18) 0.10285(16) 0.0358(5) Uani 1 1 d . . . . .
H25A H -0.0679 -0.0841 0.0394 0.054 Uiso 1 1 calc GR . . . .
H25B H -0.0479 -0.0550 0.1406 0.054 Uiso 1 1 calc GR . . . .
H25C H -0.0523 -0.2037 0.1075 0.054 Uiso 1 1 calc GR . . . .
C26 C 0.11519(10) 0.59344(17) 0.24575(13) 0.0288(5) Uani 1 1 d . . . . .
H22 H 0.0797(10) 0.6834(18) 0.1203(12) 0.021(4) Uiso 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
F1 C26 1.336(2) . ?
O2 C13 1.359(2) . ?
O2 C25 1.434(2) . ?
O3 C21 1.213(2) . ?
O4 C18 1.355(2) . ?
O4 C23 1.425(2) . ?
F5 C26 1.323(2) . ?
F6 C26 1.334(2) . ?
C7 C12 1.386(2) . ?
C7 C14 1.403(2) . ?
C7 C21 1.474(2) . ?
O8 C15 1.215(2) . ?
C9 H9 0.9300 . ?
C9 C13 1.394(3) . ?
C9 C14 1.366(3) . ?
C10 H10 0.9300 . ?
C10 C17 1.390(3) . ?
C10 C20 1.387(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(2) . ?
C11 C13 1.391(2) . ?
C12 H12 0.9300 . ?
C14 H14 0.9300 . ?
C15 C17 1.477(2) . ?
C15 C19 1.508(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.400(2) . ?
C16 C24 1.366(3) . ?
C18 C20 1.387(3) . ?
C18 C24 1.392(3) . ?
C19 C21 1.521(2) . ?
C19 C22 1.328(3) . ?
C20 H20 0.9300 . ?
C22 C26 1.482(3) . ?
C22 H22 0.982(19) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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
C13 O2 C25 118.25(13) . . ?
C18 O4 C23 118.12(14) . . ?
C12 C7 C14 118.43(15) . . ?
C12 C7 C21 122.67(15) . . ?
C14 C7 C21 118.89(15) . . ?
C13 C9 H9 120.0 . . ?
C14 C9 H9 120.0 . . ?
C14 C9 C13 120.06(15) . . ?
C17 C10 H10 119.5 . . ?
C20 C10 H10 119.5 . . ?
C20 C10 C17 121.02(16) . . ?
C12 C11 H11 120.4 . . ?
C12 C11 C13 119.10(16) . . ?
C13 C11 H11 120.4 . . ?
C7 C12 H12 119.3 . . ?
C11 C12 C7 121.42(15) . . ?
C11 C12 H12 119.3 . . ?
O2 C13 C9 115.61(14) . . ?
O2 C13 C11 124.26(16) . . ?
C11 C13 C9 120.12(15) . . ?
C7 C14 H14 119.6 . . ?
C9 C14 C7 120.86(16) . . ?
C9 C14 H14 119.6 . . ?
O8 C15 C17 122.31(17) . . ?
O8 C15 C19 118.06(16) . . ?
C17 C15 C19 119.63(15) . . ?
C17 C16 H16 119.5 . . ?
C24 C16 H16 119.5 . . ?
C24 C16 C17 121.05(17) . . ?
C10 C17 C15 123.38(15) . . ?
C10 C17 C16 118.38(16) . . ?
C16 C17 C15 118.21(16) . . ?
O4 C18 C20 124.66(17) . . ?
O4 C18 C24 115.32(15) . . ?
C20 C18 C24 120.02(16) . . ?
C15 C19 C21 113.34(15) . . ?
C22 C19 C15 119.57(16) . . ?
C22 C19 C21 127.09(16) . . ?
C10 C20 C18 119.49(17) . . ?
C10 C20 H20 120.3 . . ?
C18 C20 H20 120.3 . . ?
O3 C21 C7 123.30(16) . . ?
O3 C21 C19 117.07(15) . . ?
C7 C21 C19 119.54(15) . . ?
C19 C22 C26 125.35(17) . . ?
C19 C22 H22 123.6(10) . . ?
C26 C22 H22 111.1(10) . . ?
O4 C23 H23A 109.5 . . ?
O4 C23 H23B 109.5 . . ?
O4 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C16 C24 C18 120.03(16) . . ?
C16 C24 H24 120.0 . . ?
C18 C24 H24 120.0 . . ?
O2 C25 H25A 109.5 . . ?
O2 C25 H25B 109.5 . . ?
O2 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
F1 C26 C22 113.38(15) . . ?
F5 C26 F1 107.04(14) . . ?
F5 C26 F6 106.42(16) . . ?
F5 C26 C22 112.61(16) . . ?
F6 C26 F1 105.89(15) . . ?
F6 C26 C22 111.03(14) . . ?

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
O4 C18 C20 C10 179.64(17) . . . . ?
O4 C18 C24 C16 -179.64(16) . . . . ?
O8 C15 C17 C10 -167.63(19) . . . . ?
O8 C15 C17 C16 10.3(3) . . . . ?
O8 C15 C19 C21 56.4(2) . . . . ?
O8 C15 C19 C22 -123.9(2) . . . . ?
C12 C7 C14 C9 -1.0(3) . . . . ?
C12 C7 C21 O3 175.90(17) . . . . ?
C12 C7 C21 C19 -7.6(3) . . . . ?
C12 C11 C13 O2 178.57(16) . . . . ?
C12 C11 C13 C9 -0.9(3) . . . . ?
C13 C9 C14 C7 0.1(3) . . . . ?
C13 C11 C12 C7 -0.1(3) . . . . ?
C14 C7 C12 C11 1.0(3) . . . . ?
C14 C7 C21 O3 -3.1(3) . . . . ?
C14 C7 C21 C19 173.39(15) . . . . ?
C14 C9 C13 O2 -178.58(15) . . . . ?
C14 C9 C13 C11 0.9(3) . . . . ?
C15 C19 C21 O3 88.6(2) . . . . ?
C15 C19 C21 C7 -88.1(2) . . . . ?
C15 C19 C22 C26 177.34(17) . . . . ?
C17 C10 C20 C18 -0.3(3) . . . . ?
C17 C15 C19 C21 -123.17(16) . . . . ?
C17 C15 C19 C22 56.5(3) . . . . ?
C17 C16 C24 C18 0.2(3) . . . . ?
C19 C15 C17 C10 11.9(3) . . . . ?
C19 C15 C17 C16 -170.14(16) . . . . ?
C19 C22 C26 F1 1.5(3) . . . . ?
C19 C22 C26 F5 -120.2(2) . . . . ?
C19 C22 C26 F6 120.6(2) . . . . ?
C20 C10 C17 C15 178.42(17) . . . . ?
C20 C10 C17 C16 0.5(3) . . . . ?
C20 C18 C24 C16 0.0(3) . . . . ?
C21 C7 C12 C11 -177.94(16) . . . . ?
C21 C7 C14 C9 178.01(16) . . . . ?
C21 C19 C22 C26 -3.0(3) . . . . ?
C22 C19 C21 O3 -91.1(2) . . . . ?
C22 C19 C21 C7 92.2(2) . . . . ?
C23 O4 C18 C20 -0.6(3) . . . . ?
C23 O4 C18 C24 179.00(16) . . . . ?
C24 C16 C17 C10 -0.4(3) . . . . ?
C24 C16 C17 C15 -178.50(17) . . . . ?
C24 C18 C20 C10 0.1(3) . . . . ?
C25 O2 C13 C9 172.33(16) . . . . ?
C25 O2 C13 C11 -7.1(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_cyj-2f-4-br-3
_database_code_depnum_ccdc_archive 'CCDC 1859309'
_audit_update_record             
;
2018-07-31 deposited with the CCDC.
2018-12-07 downloaded from the CCDC.
;
_audit_creation_date             2018-07-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H12 Br2 F2 O2'
_chemical_formula_sum            'C17 H12 Br2 F2 O2'
_chemical_formula_weight         446.09
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.7491(16)
_cell_length_b                   5.8303(5)
_cell_length_c                   21.420(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.814(12)
_cell_angle_gamma                90
_cell_volume                     1652.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14553
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.403
_cell_measurement_theta_min      3.632
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.932
_exptl_absorpt_correction_T_max  0.611
_exptl_absorpt_correction_T_min  0.225
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.793
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0883
_diffrn_reflns_av_unetI/netI     0.1309
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14553
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.403
_diffrn_reflns_theta_min         3.632
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2001
_reflns_number_total             3924
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.735
_refine_diff_density_min         -0.925
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3924
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1837
_refine_ls_R_factor_gt           0.0882
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0726P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1687
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C10(H10), C11(H11), C15(H15), C16(H16), C18(H18), C23(H23)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.03632(5) 0.03159(13) 0.11271(4) 0.0645(3) Uani 1 1 d . . . . .
Br2 Br -0.14851(6) 0.06566(13) 0.50429(4) 0.0684(3) Uani 1 1 d . . . . .
C1 C -0.0973(4) -0.4751(9) 0.1927(3) 0.0322(14) Uani 1 1 d . . . . .
H1 H -0.078053 -0.615576 0.212828 0.039 Uiso 1 1 calc R . . . .
C2 C -0.2659(4) -0.5493(10) 0.2091(3) 0.0349(14) Uani 1 1 d . . . . .
O2 O -0.2381(3) -0.7337(7) 0.2331(2) 0.0511(12) Uani 1 1 d . . . . .
C4 C -0.1960(4) -0.3987(9) 0.1844(3) 0.0284(13) Uani 1 1 d . . . . .
C5 C -0.1541(4) -0.0637(10) 0.1327(3) 0.0383(15) Uani 1 1 d . . . . .
H5 H -0.172464 0.077024 0.112480 0.046 Uiso 1 1 calc R . . . .
O1 O -0.4459(3) -0.6535(8) 0.2822(2) 0.0509(12) Uani 1 1 d . . . . .
C7 C -0.3281(4) -0.3654(10) 0.3277(3) 0.0309(14) Uani 1 1 d . . . . .
C8 C -0.0588(4) -0.1447(10) 0.1421(3) 0.0339(14) Uani 1 1 d . . . . .
C9 C -0.3886(4) -0.5081(10) 0.2733(3) 0.0329(14) Uani 1 1 d . . . . .
C10 C -0.2321(4) -0.0307(10) 0.3700(3) 0.0395(16) Uani 1 1 d . . . . .
H10 H -0.203978 0.108897 0.363023 0.047 Uiso 1 1 calc R . . . .
C11 C -0.0280(4) -0.3505(10) 0.1721(3) 0.0386(15) Uani 1 1 d . . . . .
H11 H 0.037738 -0.403168 0.178077 0.046 Uiso 1 1 calc R . . . .
C12 C -0.2225(5) -0.1122(11) 0.4332(3) 0.0426(16) Uani 1 1 d . . . . .
C14 C -0.3741(4) -0.4696(9) 0.2060(3) 0.0330(14) Uani 1 1 d . . . . .
H14 H -0.381492 -0.306163 0.195018 0.040 Uiso 1 1 calc R . . . .
C15 C -0.3199(5) -0.4406(10) 0.3908(3) 0.0402(15) Uani 1 1 d . . . . .
H15 H -0.351304 -0.576257 0.397388 0.048 Uiso 1 1 calc R . . . .
C16 C -0.2655(5) -0.3150(11) 0.4434(3) 0.0481(17) Uani 1 1 d . . . . .
H16 H -0.258237 -0.367912 0.485416 0.058 Uiso 1 1 calc R . . . .
C17 C -0.4525(5) -0.6072(12) 0.1564(3) 0.0515(18) Uani 1 1 d . . . . .
H17A H -0.440838 -0.768594 0.166696 0.062 Uiso 1 1 calc R . . . .
H17B H -0.518697 -0.569326 0.161293 0.062 Uiso 1 1 calc R . . . .
C18 C -0.2838(4) -0.1624(10) 0.3193(3) 0.0369(15) Uani 1 1 d . . . . .
H18 H -0.289108 -0.112208 0.277337 0.044 Uiso 1 1 calc R . . . .
F1 F -0.3670(4) -0.6405(12) 0.0762(2) 0.123(2) Uani 1 1 d . . . . .
C22 C -0.4551(6) -0.5744(17) 0.0875(4) 0.078(3) Uani 1 1 d . . . . .
H22 H -0.511693 -0.659956 0.059420 0.094 Uiso 1 1 calc R . . . .
C23 C -0.2236(4) -0.1924(9) 0.1534(3) 0.0327(14) Uani 1 1 d . . . . .
H23 H -0.289518 -0.139505 0.146341 0.039 Uiso 1 1 calc R . . . .
F2 F -0.4636(4) -0.3470(12) 0.0720(2) 0.127(2) 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
Br1 C8 1.900(5) . ?
Br2 C12 1.893(6) . ?
C1 C4 1.393(7) . ?
C1 C11 1.363(7) . ?
C2 O2 1.208(6) . ?
C2 C4 1.501(8) . ?
C2 C14 1.543(8) . ?
C4 C23 1.377(8) . ?
C5 C8 1.355(8) . ?
C5 C23 1.380(8) . ?
O1 C9 1.208(6) . ?
C7 C9 1.488(8) . ?
C7 C15 1.395(8) . ?
C7 C18 1.365(8) . ?
C8 C11 1.372(8) . ?
C9 C14 1.525(8) . ?
C10 C12 1.408(9) . ?
C10 C18 1.361(8) . ?
C12 C16 1.366(9) . ?
C14 C17 1.520(8) . ?
C15 C16 1.382(9) . ?
C17 C22 1.479(10) . ?
F1 C22 1.355(10) . ?
C22 F2 1.364(10) . ?

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
C11 C1 C4 122.1(5) . . ?
O2 C2 C4 120.8(5) . . ?
O2 C2 C14 118.4(5) . . ?
C4 C2 C14 120.8(5) . . ?
C1 C4 C2 117.6(5) . . ?
C23 C4 C1 118.1(5) . . ?
C23 C4 C2 124.2(5) . . ?
C8 C5 C23 119.3(5) . . ?
C15 C7 C9 117.6(5) . . ?
C18 C7 C9 123.8(5) . . ?
C18 C7 C15 118.6(6) . . ?
C5 C8 Br1 119.1(5) . . ?
C5 C8 C11 122.5(5) . . ?
C11 C8 Br1 118.4(4) . . ?
O1 C9 C7 121.3(5) . . ?
O1 C9 C14 120.7(5) . . ?
C7 C9 C14 118.0(5) . . ?
C18 C10 C12 117.9(6) . . ?
C1 C11 C8 117.6(5) . . ?
C10 C12 Br2 118.5(5) . . ?
C16 C12 Br2 120.4(5) . . ?
C16 C12 C10 121.0(6) . . ?
C9 C14 C2 106.7(5) . . ?
C17 C14 C2 111.3(5) . . ?
C17 C14 C9 109.5(5) . . ?
C16 C15 C7 120.4(6) . . ?
C12 C16 C15 119.3(6) . . ?
C22 C17 C14 116.7(6) . . ?
C10 C18 C7 122.6(6) . . ?
F1 C22 C17 111.2(7) . . ?
F1 C22 F2 104.7(7) . . ?
F2 C22 C17 110.2(7) . . ?
C4 C23 C5 120.4(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
