# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1518394'
_audit_update_record             
;
2016-11-21 deposited with the CCDC.
2017-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
4-(4-bromophenyl)-2-fluoro-N-phenylchromane-5-carboxamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         C22H17BrFNO2
_chemical_formula_sum            'C22 H17 Br F N O2'
_chemical_formula_weight         426.27

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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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'

_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                   15.3026(6)
_cell_length_b                   12.0184(4)
_cell_length_c                   10.1214(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.552(3)
_cell_angle_gamma                90
_cell_volume                     1861.37(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9817
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      68.28

_exptl_crystal_description       Needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    3.238
_shelx_estimated_absorpt_T_min   0.829
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6139
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus rotating anode'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.366
_diffrn_reflns_number            24648
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.888
_diffrn_reflns_theta_max         68.325
_diffrn_reflns_theta_full        67.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3399
_reflns_number_gt                2939
_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    Sir-2011
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX

_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)+(0.0448P)²+2.6265P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3399
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0963
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
C1 C 0.13655(17) -0.2975(2) 0.9430(3) 0.0210(5) Uani 1 1 d . . . . .
C2 C 0.22180(17) -0.3351(2) 0.9158(3) 0.0226(5) Uani 1 1 d . . . . .
C3 C 0.23665(18) -0.4394(2) 0.8630(3) 0.0246(6) Uani 1 1 d . . . . .
H3 H 0.2946 -0.4627 0.8443 0.030 Uiso 1 1 calc R U . . .
C4 C 0.16643(19) -0.5106(2) 0.8371(3) 0.0262(6) Uani 1 1 d . . . . .
H4 H 0.1767 -0.5836 0.8048 0.031 Uiso 1 1 calc R U . . .
C5 C 0.08232(18) -0.4749(2) 0.8586(3) 0.0248(6) Uani 1 1 d . . . . .
H5 H 0.0343 -0.5223 0.8389 0.030 Uiso 1 1 calc R U . . .
C6 C 0.06801(17) -0.3686(2) 0.9094(3) 0.0226(5) Uani 1 1 d . . . . .
C7 C -0.03863(18) -0.2307(2) 0.9520(3) 0.0272(6) Uani 1 1 d . . . . .
H7 H -0.0991 -0.2264 0.9881 0.033 Uiso 1 1 calc R U . . .
C8 C 0.02331(17) -0.1759(2) 1.0480(3) 0.0256(6) Uani 1 1 d . . . . .
H8A H 0.0167 -0.2109 1.1359 0.031 Uiso 1 1 calc R U . . .
H8B H 0.0076 -0.0964 1.0564 0.031 Uiso 1 1 calc R U . . .
C9 C 0.11952(17) -0.1850(2) 1.0055(3) 0.0225(5) Uani 1 1 d . . . . .
H9 H 0.1554 -0.1827 1.0886 0.027 Uiso 1 1 calc R U . . .
C10 C 0.29930(17) -0.2631(2) 0.9515(3) 0.0227(5) Uani 1 1 d . . . . .
C11 C 0.42919(18) -0.1739(2) 0.8571(3) 0.0284(6) Uani 1 1 d . . . . .
C12 C 0.4440(2) -0.0950(3) 0.7600(3) 0.0342(7) Uani 1 1 d . . . . .
H12 H 0.4032 -0.0854 0.6896 0.041 Uiso 1 1 calc R U . . .
C13 C 0.5193(2) -0.0298(3) 0.7664(4) 0.0422(8) Uani 1 1 d . . . . .
H13 H 0.5301 0.0241 0.6998 0.051 Uiso 1 1 calc R U . . .
C14 C 0.5783(2) -0.0435(3) 0.8692(4) 0.0421(8) Uani 1 1 d . . . . .
H14 H 0.6295 0.0012 0.8737 0.051 Uiso 1 1 calc R U . . .
C15 C 0.56289(19) -0.1215(3) 0.9650(4) 0.0400(8) Uani 1 1 d . . . . .
H15 H 0.6034 -0.1300 1.0360 0.048 Uiso 1 1 calc R U . . .
C16 C 0.48884(19) -0.1887(3) 0.9598(3) 0.0326(7) Uani 1 1 d . . . . .
H16 H 0.4793 -0.2437 1.0255 0.039 Uiso 1 1 calc R U . . .
C17 C 0.15131(16) -0.0890(2) 0.9198(3) 0.0208(5) Uani 1 1 d . . . . .
C18 C 0.15159(18) -0.0926(2) 0.7825(3) 0.0259(6) Uani 1 1 d . . . . .
H18 H 0.1276 -0.1555 0.7384 0.031 Uiso 1 1 calc R U . . .
C19 C 0.1861(2) -0.0063(2) 0.7087(3) 0.0284(6) Uani 1 1 d . . . . .
H19 H 0.1856 -0.0095 0.6149 0.034 Uiso 1 1 calc R U . . .
C20 C 0.22149(17) 0.0845(2) 0.7741(3) 0.0239(6) Uani 1 1 d . . . . .
C21 C 0.22003(17) 0.0921(2) 0.9092(3) 0.0238(5) Uani 1 1 d . . . . .
H21 H 0.2428 0.1560 0.9528 0.029 Uiso 1 1 calc R U . . .
C22 C 0.18493(17) 0.0054(2) 0.9813(3) 0.0243(6) Uani 1 1 d . . . . .
H22 H 0.1838 0.0105 1.0749 0.029 Uiso 1 1 calc R U . . .
N1 N 0.35188(15) -0.24005(19) 0.8484(2) 0.0255(5) Uani 1 1 d . . . . .
H1 H 0.3375 -0.2677 0.7707 0.031 Uiso 1 1 calc R U . . .
O1 O -0.01898(12) -0.34135(16) 0.9261(2) 0.0267(4) Uani 1 1 d . . . . .
O2 O 0.31282(12) -0.23216(17) 1.06530(19) 0.0269(4) Uani 1 1 d . . . . .
F1 F -0.03651(11) -0.17305(14) 0.83137(17) 0.0307(4) Uani 1 1 d . . . . .
Br1 Br 0.27914(2) 0.19816(2) 0.67744(3) 0.03346(12) 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
C1 C6 1.393(4) . ?
C1 C2 1.410(4) . ?
C1 C9 1.516(4) . ?
C2 C3 1.383(4) . ?
C2 C10 1.509(4) . ?
C3 C4 1.396(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(4) . ?
C5 H5 0.9500 . ?
C6 O1 1.383(3) . ?
C7 O1 1.389(3) . ?
C7 F1 1.405(3) . ?
C7 C8 1.502(4) . ?
C7 H7 1.0000 . ?
C8 C9 1.542(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C17 1.526(4) . ?
C9 H9 1.0000 . ?
C10 O2 1.226(3) . ?
C10 N1 1.353(4) . ?
C11 C12 1.385(4) . ?
C11 C16 1.389(4) . ?
C11 N1 1.428(4) . ?
C12 C13 1.395(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.371(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.392(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.390(4) . ?
C17 C22 1.391(4) . ?
C18 C19 1.386(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.384(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.371(4) . ?
C20 Br1 1.902(3) . ?
C21 C22 1.383(4) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
N1 H1 0.8800 . ?

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
C6 C1 C2 116.8(2) . . ?
C6 C1 C9 121.2(2) . . ?
C2 C1 C9 122.1(2) . . ?
C3 C2 C1 121.5(2) . . ?
C3 C2 C10 118.7(2) . . ?
C1 C2 C10 119.7(2) . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
O1 C6 C1 123.2(2) . . ?
O1 C6 C5 114.7(2) . . ?
C1 C6 C5 122.1(2) . . ?
O1 C7 F1 107.5(2) . . ?
O1 C7 C8 113.9(2) . . ?
F1 C7 C8 109.1(2) . . ?
O1 C7 H7 108.8 . . ?
F1 C7 H7 108.8 . . ?
C8 C7 H7 108.8 . . ?
C7 C8 C9 112.8(2) . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C1 C9 C17 112.3(2) . . ?
C1 C9 C8 110.4(2) . . ?
C17 C9 C8 114.6(2) . . ?
C1 C9 H9 106.3 . . ?
C17 C9 H9 106.3 . . ?
C8 C9 H9 106.3 . . ?
O2 C10 N1 124.5(3) . . ?
O2 C10 C2 121.6(2) . . ?
N1 C10 C2 113.9(2) . . ?
C12 C11 C16 120.5(3) . . ?
C12 C11 N1 118.6(3) . . ?
C16 C11 N1 120.9(3) . . ?
C11 C12 C13 119.5(3) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 119.9(3) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 121.1(3) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C11 C16 C15 118.9(3) . . ?
C11 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C18 C17 C22 117.9(2) . . ?
C18 C17 C9 123.3(2) . . ?
C22 C17 C9 118.8(2) . . ?
C19 C18 C17 121.4(3) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C20 C19 C18 118.8(3) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
C21 C20 C19 121.3(3) . . ?
C21 C20 Br1 118.5(2) . . ?
C19 C20 Br1 120.1(2) . . ?
C20 C21 C22 119.1(2) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C21 C22 C17 121.5(3) . . ?
C21 C22 H22 119.3 . . ?
C17 C22 H22 119.3 . . ?
C10 N1 C11 124.4(2) . . ?
C10 N1 H1 117.8 . . ?
C11 N1 H1 117.8 . . ?
C6 O1 C7 117.4(2) . . ?

_refine_diff_density_max         0.870
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.074

_shelxl_version_number           2014-1


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/Pentane'
