# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_1412
_database_code_depnum_ccdc_archive 'CCDC 1942072'
loop_
_audit_author_name
_audit_author_address
'Jian Li'
;School of Chemistry and  Pharmacy, Northwest A and F University, Yangling, China
China
;
_audit_update_record             
;
2019-07-22 deposited with the CCDC.	2021-06-25 downloaded from the CCDC.
;
_audit_creation_date             2018-04-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H17 Br O2'
_chemical_formula_sum            'C25 H17 Br O2'
_chemical_formula_weight         429.29
_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'
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                   13.3654(9)
_cell_length_b                   10.6073(9)
_cell_length_c                   13.4584(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.914(6)
_cell_angle_gamma                90
_cell_volume                     1907.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2918
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.4520
_cell_measurement_theta_min      2.8540
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.173
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7754
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         2.445
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     41.00  99.00   1.00    4.75    --   11.74-178.00-120.00   58
  2  ω      6.00  82.00   1.00    4.75    --   11.74  37.00 -60.00   76
  3  ω     14.00  64.00   1.00    4.75    --   11.74  37.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0089711000
_diffrn_orient_matrix_UB_12      0.0628955000
_diffrn_orient_matrix_UB_13      0.0152037000
_diffrn_orient_matrix_UB_21      0.0522402000
_diffrn_orient_matrix_UB_22      0.0089736000
_diffrn_orient_matrix_UB_23      0.0076539000
_diffrn_orient_matrix_UB_31      0.0043422000
_diffrn_orient_matrix_UB_32      0.0206729000
_diffrn_orient_matrix_UB_33      -0.0498243000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2699
_reflns_number_total             3320
_reflns_odcompleteness_completeness 98.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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         0.715
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3320
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0403P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0993
_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 Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C19(H19), C18(H18), C15(H15), C2(H2), C16(H16), C23(H23), C22(H22),
 C25(H25), C5(H5), C3(H3), C24(H24), C4(H4)
;
_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 0.39343(3) 0.70840(4) 0.12794(2) 0.02652(15) Uani 1 1 d . . . . .
O2 O 0.66101(16) 0.9628(2) 0.51688(15) 0.0207(5) Uani 1 1 d . . . . .
O1 O 0.86501(16) 0.8996(2) 0.57539(15) 0.0216(5) Uani 1 1 d . . . . .
C14 C 0.6049(2) 0.8211(3) 0.3921(2) 0.0163(7) Uani 1 1 d . . . . .
C17 C 0.4802(2) 0.7555(3) 0.2340(2) 0.0178(8) Uani 1 1 d . . . . .
C13 C 0.6676(2) 0.8582(3) 0.4806(2) 0.0168(8) Uani 1 1 d . . . . .
C21 C 0.7952(2) 0.3121(3) 0.5649(2) 0.0184(8) Uani 1 1 d . . . . .
H21 H 0.755851 0.287273 0.617832 0.022 Uiso 1 1 calc R . . . .
C19 C 0.5118(2) 0.8778(3) 0.3794(2) 0.0181(8) Uani 1 1 d . . . . .
H19 H 0.491739 0.939341 0.424047 0.022 Uiso 1 1 calc R . . . .
C18 C 0.4486(2) 0.8445(3) 0.3018(2) 0.0185(8) Uani 1 1 d . . . . .
H18 H 0.385706 0.881336 0.295083 0.022 Uiso 1 1 calc R . . . .
C10 C 0.7038(2) 0.6398(3) 0.5347(2) 0.0148(7) Uani 1 1 d . . . . .
C9 C 0.6081(2) 0.5679(3) 0.5203(2) 0.0189(8) Uani 1 1 d . . . . .
H9A H 0.606783 0.513229 0.462514 0.023 Uiso 1 1 calc R . . . .
H9B H 0.548198 0.619341 0.523352 0.023 Uiso 1 1 calc R . . . .
C15 C 0.6356(3) 0.7314(3) 0.3232(2) 0.0183(8) Uani 1 1 d . . . . .
H15 H 0.697852 0.693077 0.330772 0.022 Uiso 1 1 calc R . . . .
C11 C 0.7323(2) 0.7604(3) 0.5286(2) 0.0146(7) Uani 1 1 d . . . . .
C2 C 0.9087(2) 0.7684(3) 0.7514(2) 0.0190(8) Uani 1 1 d . . . . .
H2 H 0.931954 0.850646 0.745901 0.023 Uiso 1 1 calc R . . . .
C16 C 0.5738(2) 0.6990(3) 0.2434(2) 0.0181(8) Uani 1 1 d . . . . .
H16 H 0.594707 0.640211 0.196798 0.022 Uiso 1 1 calc R . . . .
C20 C 0.8038(2) 0.4386(3) 0.5424(2) 0.0157(7) Uani 1 1 d . . . . .
C8 C 0.6365(2) 0.5002(3) 0.6196(2) 0.0196(8) Uani 1 1 d . . . . .
H8A H 0.625521 0.409808 0.618366 0.023 Uiso 1 1 calc R . . . .
H8B H 0.607265 0.538180 0.677900 0.023 Uiso 1 1 calc R . . . .
C6 C 0.8124(2) 0.5941(3) 0.6845(2) 0.0169(8) Uani 1 1 d . . . . .
C7 C 0.7487(2) 0.5403(3) 0.6017(2) 0.0162(7) Uani 1 1 d . . . . .
C12 C 0.8207(2) 0.8010(3) 0.5902(2) 0.0152(7) Uani 1 1 d . . . . .
C23 C 0.9038(2) 0.2580(3) 0.4317(2) 0.0214(8) Uani 1 1 d . . . . .
H23 H 0.937261 0.197710 0.394661 0.026 Uiso 1 1 calc R . . . .
C22 C 0.8447(2) 0.2211(3) 0.5094(2) 0.0217(8) Uani 1 1 d . . . . .
H22 H 0.837865 0.136101 0.524706 0.026 Uiso 1 1 calc R . . . .
C25 C 0.8640(2) 0.4743(3) 0.4642(2) 0.0220(8) Uani 1 1 d . . . . .
H25 H 0.871387 0.559295 0.448976 0.026 Uiso 1 1 calc R . . . .
C5 C 0.8401(2) 0.5235(3) 0.7679(2) 0.0211(8) Uani 1 1 d . . . . .
H5 H 0.818014 0.440697 0.773718 0.025 Uiso 1 1 calc R . . . .
C3 C 0.9344(3) 0.6981(3) 0.8340(2) 0.0221(8) Uani 1 1 d . . . . .
H3 H 0.974585 0.732686 0.884053 0.026 Uiso 1 1 calc R . . . .
C1 C 0.8481(2) 0.7179(3) 0.6758(2) 0.0156(7) Uani 1 1 d . . . . .
C24 C 0.9134(3) 0.3840(3) 0.4087(2) 0.0240(8) Uani 1 1 d . . . . .
H24 H 0.953019 0.408516 0.355859 0.029 Uiso 1 1 calc R . . . .
C4 C 0.8998(2) 0.5749(3) 0.8419(2) 0.0238(8) Uani 1 1 d . . . . .
H4 H 0.917048 0.526923 0.897428 0.029 Uiso 1 1 calc R . . . .


_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 C17 1.892(3) . ?
O2 C13 1.216(4) . ?
O1 C12 1.219(4) . ?
C14 C13 1.498(5) . ?
C14 C19 1.390(4) . ?
C14 C15 1.395(5) . ?
C17 C18 1.384(5) . ?
C17 C16 1.391(5) . ?
C13 C11 1.492(5) . ?
C21 H21 0.9300 . ?
C21 C20 1.381(5) . ?
C21 C22 1.394(5) . ?
C19 H19 0.9300 . ?
C19 C18 1.378(4) . ?
C18 H18 0.9300 . ?
C10 C9 1.499(4) . ?
C10 C11 1.338(5) . ?
C10 C7 1.507(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.559(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.387(5) . ?
C11 C12 1.496(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(5) . ?
C2 C1 1.397(4) . ?
C16 H16 0.9300 . ?
C20 C7 1.536(4) . ?
C20 C25 1.388(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.581(4) . ?
C6 C7 1.504(4) . ?
C6 C5 1.396(4) . ?
C6 C1 1.402(5) . ?
C12 C1 1.492(4) . ?
C23 H23 0.9300 . ?
C23 C22 1.377(5) . ?
C23 C24 1.378(5) . ?
C22 H22 0.9300 . ?
C25 H25 0.9300 . ?
C25 C24 1.389(5) . ?
C5 H5 0.9300 . ?
C5 C4 1.378(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(5) . ?
C24 H24 0.9300 . ?
C4 H4 0.9300 . ?

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
C19 C14 C13 118.2(3) . . ?
C19 C14 C15 119.0(3) . . ?
C15 C14 C13 122.7(3) . . ?
C18 C17 Br1 119.2(3) . . ?
C18 C17 C16 121.2(3) . . ?
C16 C17 Br1 119.6(3) . . ?
O2 C13 C14 121.1(3) . . ?
O2 C13 C11 120.4(3) . . ?
C11 C13 C14 118.4(3) . . ?
C20 C21 H21 119.6 . . ?
C20 C21 C22 120.9(3) . . ?
C22 C21 H21 119.6 . . ?
C14 C19 H19 119.4 . . ?
C18 C19 C14 121.3(3) . . ?
C18 C19 H19 119.4 . . ?
C17 C18 H18 120.5 . . ?
C19 C18 C17 119.0(3) . . ?
C19 C18 H18 120.5 . . ?
C11 C10 C9 136.2(3) . . ?
C11 C10 C7 126.6(3) . . ?
C7 C10 C9 93.0(3) . . ?
C10 C9 H9A 114.3 . . ?
C10 C9 H9B 114.3 . . ?
C10 C9 C8 85.9(2) . . ?
H9A C9 H9B 111.5 . . ?
C8 C9 H9A 114.3 . . ?
C8 C9 H9B 114.3 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(3) . . ?
C16 C15 H15 119.8 . . ?
C10 C11 C13 121.9(3) . . ?
C10 C11 C12 117.7(3) . . ?
C12 C11 C13 119.2(3) . . ?
C3 C2 H2 119.5 . . ?
C3 C2 C1 121.0(3) . . ?
C1 C2 H2 119.5 . . ?
C17 C16 H16 120.4 . . ?
C15 C16 C17 119.1(3) . . ?
C15 C16 H16 120.4 . . ?
C21 C20 C7 121.7(3) . . ?
C21 C20 C25 118.9(3) . . ?
C25 C20 C7 119.4(3) . . ?
C9 C8 H8A 114.0 . . ?
C9 C8 H8B 114.0 . . ?
C9 C8 C7 88.0(2) . . ?
H8A C8 H8B 111.2 . . ?
C7 C8 H8A 114.0 . . ?
C7 C8 H8B 114.0 . . ?
C5 C6 C7 122.1(3) . . ?
C5 C6 C1 118.9(3) . . ?
C1 C6 C7 118.9(3) . . ?
C10 C7 C20 111.7(3) . . ?
C10 C7 C8 84.8(2) . . ?
C10 C7 C6 113.1(3) . . ?
C20 C7 C8 110.7(3) . . ?
C6 C7 C20 112.4(3) . . ?
C6 C7 C8 121.1(3) . . ?
O1 C12 C11 122.5(3) . . ?
O1 C12 C1 121.3(3) . . ?
C1 C12 C11 116.1(3) . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.2(3) . . ?
C24 C23 H23 119.9 . . ?
C21 C22 H22 120.2 . . ?
C23 C22 C21 119.6(3) . . ?
C23 C22 H22 120.2 . . ?
C20 C25 H25 119.8 . . ?
C20 C25 C24 120.4(3) . . ?
C24 C25 H25 119.8 . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C1 C6 119.5(3) . . ?
C2 C1 C12 117.9(3) . . ?
C6 C1 C12 122.6(3) . . ?
C23 C24 C25 120.1(3) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.217
_oxdiff_exptl_absorpt_empirical_full_min 0.793
