# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_181016a_sq_s
_database_code_depnum_ccdc_archive 'CCDC 1968925'
loop_
_audit_author_name
_audit_author_address
'HONGYIN GAO'
;Shandong University
China
;
_audit_update_record             
;
2020-03-09 deposited with the CCDC.	2020-06-10 downloaded from the CCDC.
;
_audit_creation_date             2018-10-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H16 F3 N O2'
_chemical_formula_sum            'C24 H16 F3 N O2'
_chemical_formula_weight         407.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         CNOF
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'
F F 0.0727 0.0534 '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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   15.0044(8)
_cell_length_b                   8.2203(3)
_cell_length_c                   19.4734(10)
_cell_angle_alpha                90
_cell_angle_beta                 108.910(5)
_cell_angle_gamma                90
_cell_volume                     2272.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3629
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      76.4970
_cell_measurement_theta_min      4.7410
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.782
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12336
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.059
_diffrn_reflns_theta_min         3.257
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -48.00  26.00   1.00    0.70    --  -48.45  15.00  44.00   74
  2  ω   -123.00 -38.00   1.00    0.70    --  -48.45 -15.00-126.00   85
  3  ω     55.00  81.00   1.00    0.70    --   48.45  15.00  44.00   26
  4  ω    -19.00   7.00   1.00    0.70    --   48.45 -15.00-126.00   26
  5  ω    -80.00 -55.00   1.00    6.00    --  -86.25  15.00  44.00   25
  6  ω   -142.00-101.00   1.00    6.00    --  -86.25 -15.00-126.00   41
  7  ω     97.00 176.00   1.00    6.00    --  107.75  15.00  44.00   79
  8  ω     34.00 108.00   1.00    6.00    --  107.75 -15.00-126.00   74
  9  ω    -24.00  61.00   1.00    0.70    --   48.45 -37.00 120.00   85
 10  ω     35.00 120.00   1.00    6.00    --  107.75 -37.00-150.00   85
 11  ω     35.00 117.00   1.00    6.00    --  107.75-125.00-120.00   82
 12  ω     49.00 108.00   1.00    6.00    --  107.75 -99.00   0.00   59
 13  ω     35.00 109.00   1.00    6.00    --  107.75 -99.00-120.00   74
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0003964000
_diffrn_orient_matrix_UB_12      0.0281041000
_diffrn_orient_matrix_UB_13      0.0783227000
_diffrn_orient_matrix_UB_21      -0.1076527000
_diffrn_orient_matrix_UB_22      -0.0237017000
_diffrn_orient_matrix_UB_23      -0.0251212000
_diffrn_orient_matrix_UB_31      0.0140803000
_diffrn_orient_matrix_UB_32      -0.1836957000
_diffrn_orient_matrix_UB_33      0.0152125000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2986
_reflns_number_total             4025
_reflns_odcompleteness_completeness 99.18
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_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    ?
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4025
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0666
_refine_ls_restrained_S_all      1.055
_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)+(0.1121P)²+0.7710P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1903
_refine_ls_wR_factor_ref         0.2101
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C23(H23), C4(H4), C20(H20), C17(H17), C8(H8), C1(H1B), C3(H3),
 C13(H13), C21(H21), C2(H2), C7(H7), C14(H14), C16(H16), C15(H15)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.53369(14) 0.2214(2) 0.63131(10) 0.0551(5) Uani 1 1 d . . . . .
H1 H 0.5101 0.1305 0.6277 0.083 Uiso 1 1 calc GR . . . .
O2 O 0.46179(14) 0.9184(2) 0.60765(11) 0.0608(5) Uani 1 1 d . . . . .
N1 N 0.44757(15) 0.6911(2) 0.54182(11) 0.0483(5) Uani 1 1 d . . . . .
H1A H 0.4095 0.6239 0.5129 0.058 Uiso 1 1 calc R . . . .
C10 C 0.57820(16) 0.5513(3) 0.63159(12) 0.0401(5) Uani 1 1 d . . . . .
C5 C 0.67740(17) 0.5204(3) 0.66067(13) 0.0426(5) Uani 1 1 d . . . . .
C18 C 0.51302(17) 0.4858(3) 0.66866(13) 0.0432(5) Uani 1 1 d . . . . .
C11 C 0.41338(18) 0.8311(3) 0.55775(13) 0.0454(6) Uani 1 1 d . . . . .
C9 C 0.54499(18) 0.6490(3) 0.57110(13) 0.0456(6) Uani 1 1 d . . . . .
C12 C 0.31487(19) 0.8759(3) 0.51461(14) 0.0491(6) Uani 1 1 d . . . . .
C19 C 0.49201(17) 0.3206(3) 0.66764(14) 0.0451(6) Uani 1 1 d . . . . .
C23 C 0.47215(18) 0.5902(3) 0.70570(14) 0.0485(6) Uani 1 1 d . . . . .
H23 H 0.4858 0.7007 0.7070 0.058 Uiso 1 1 calc R . . . .
C6 C 0.73868(18) 0.5887(3) 0.62617(14) 0.0488(6) Uani 1 1 d . . . . .
C4 C 0.71784(19) 0.4304(3) 0.72527(15) 0.0517(6) Uani 1 1 d . . . . .
H4 H 0.6790 0.3835 0.7485 0.062 Uiso 1 1 calc R . . . .
F1 F 0.3417(3) 0.7860(4) 0.7450(2) 0.1625(17) Uani 1 1 d . . . . .
C22 C 0.4115(2) 0.5336(4) 0.74073(16) 0.0579(7) Uani 1 1 d . . . . .
C20 C 0.4314(2) 0.2635(3) 0.70264(17) 0.0594(7) Uani 1 1 d . . . . .
H20 H 0.4173 0.1531 0.7012 0.071 Uiso 1 1 calc R . . . .
C17 C 0.2605(2) 0.9570(4) 0.54924(17) 0.0623(7) Uani 1 1 d . . . . .
H17 H 0.2855 0.9802 0.5985 0.075 Uiso 1 1 calc R . . . .
C8 C 0.6068(2) 0.7149(3) 0.53706(15) 0.0580(7) Uani 1 1 d . . . . .
H8 H 0.5830 0.7799 0.4961 0.070 Uiso 1 1 calc R . . . .
C1 C 0.8369(2) 0.5640(4) 0.65677(18) 0.0599(7) Uani 1 1 d . . . . .
H1B H 0.8772 0.6067 0.6338 0.072 Uiso 1 1 calc R . . . .
C3 C 0.8129(2) 0.4117(3) 0.75371(18) 0.0628(8) Uani 1 1 d . . . . .
H3 H 0.8382 0.3536 0.7966 0.075 Uiso 1 1 calc R . . . .
C13 C 0.2779(2) 0.8438(4) 0.44084(16) 0.0614(7) Uani 1 1 d . . . . .
H13 H 0.3140 0.7897 0.4172 0.074 Uiso 1 1 calc R . . . .
C21 C 0.3917(2) 0.3687(4) 0.73954(19) 0.0641(8) Uani 1 1 d . . . . .
H21 H 0.3518 0.3292 0.7636 0.077 Uiso 1 1 calc R . . . .
C2 C 0.8731(2) 0.4786(4) 0.71934(19) 0.0653(8) Uani 1 1 d . . . . .
H2 H 0.9379 0.4645 0.7394 0.078 Uiso 1 1 calc R . . . .
C7 C 0.7003(2) 0.6844(4) 0.56354(16) 0.0621(7) Uani 1 1 d . . . . .
H7 H 0.7399 0.7272 0.5400 0.075 Uiso 1 1 calc R . . . .
F2 F 0.2970(3) 0.5977(4) 0.7941(3) 0.181(2) Uani 1 1 d . . . . .
C24 C 0.3681(3) 0.6498(5) 0.7781(2) 0.0784(10) Uani 1 1 d . . . . .
C14 C 0.1872(3) 0.8924(4) 0.4026(2) 0.0788(10) Uani 1 1 d . . . . .
H14 H 0.1625 0.8719 0.3530 0.095 Uiso 1 1 calc R . . . .
F3 F 0.4255(3) 0.7003(7) 0.8401(2) 0.217(3) Uani 1 1 d . . . . .
C16 C 0.1696(2) 1.0034(5) 0.5110(2) 0.0797(10) Uani 1 1 d . . . . .
H16 H 0.1330 1.0562 0.5346 0.096 Uiso 1 1 calc R . . . .
C15 C 0.1332(2) 0.9711(5) 0.4376(2) 0.0851(11) Uani 1 1 d . . . . .
H15 H 0.0719 1.0025 0.4117 0.102 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
O1 H1 0.8200 . ?
O1 C19 1.358(3) . ?
O2 C11 1.237(3) . ?
N1 H1A 0.8600 . ?
N1 C11 1.337(3) . ?
N1 C9 1.429(3) . ?
C10 C5 1.433(3) . ?
C10 C18 1.492(3) . ?
C10 C9 1.378(3) . ?
C5 C6 1.418(4) . ?
C5 C4 1.415(3) . ?
C18 C19 1.392(3) . ?
C18 C23 1.386(4) . ?
C11 C12 1.490(4) . ?
C9 C8 1.411(4) . ?
C12 C17 1.386(4) . ?
C12 C13 1.387(4) . ?
C19 C20 1.383(4) . ?
C23 H23 0.9300 . ?
C23 C22 1.383(4) . ?
C6 C1 1.414(4) . ?
C6 C7 1.408(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.361(4) . ?
F1 C24 1.288(5) . ?
C22 C21 1.387(4) . ?
C22 C24 1.473(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.377(4) . ?
C17 H17 0.9300 . ?
C17 C16 1.379(5) . ?
C8 H8 0.9300 . ?
C8 C7 1.353(4) . ?
C1 H1B 0.9300 . ?
C1 C2 1.358(4) . ?
C3 H3 0.9300 . ?
C3 C2 1.400(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(5) . ?
C21 H21 0.9300 . ?
C2 H2 0.9300 . ?
C7 H7 0.9300 . ?
F2 C24 1.280(5) . ?
C24 F3 1.303(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(6) . ?
C16 H16 0.9300 . ?
C16 C15 1.381(6) . ?
C15 H15 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 O1 H1 109.5 . . ?
C11 N1 H1A 118.8 . . ?
C11 N1 C9 122.4(2) . . ?
C9 N1 H1A 118.8 . . ?
C5 C10 C18 120.3(2) . . ?
C9 C10 C5 118.8(2) . . ?
C9 C10 C18 120.8(2) . . ?
C6 C5 C10 119.5(2) . . ?
C4 C5 C10 122.3(2) . . ?
C4 C5 C6 118.1(2) . . ?
C19 C18 C10 121.7(2) . . ?
C23 C18 C10 119.9(2) . . ?
C23 C18 C19 118.4(2) . . ?
O2 C11 N1 120.7(2) . . ?
O2 C11 C12 121.5(2) . . ?
N1 C11 C12 117.9(2) . . ?
C10 C9 N1 121.5(2) . . ?
C10 C9 C8 121.0(2) . . ?
C8 C9 N1 117.5(2) . . ?
C17 C12 C11 118.5(2) . . ?
C17 C12 C13 119.6(3) . . ?
C13 C12 C11 121.8(2) . . ?
O1 C19 C18 116.9(2) . . ?
O1 C19 C20 122.7(2) . . ?
C20 C19 C18 120.4(2) . . ?
C18 C23 H23 119.3 . . ?
C22 C23 C18 121.4(2) . . ?
C22 C23 H23 119.3 . . ?
C1 C6 C5 119.4(2) . . ?
C7 C6 C5 119.0(2) . . ?
C7 C6 C1 121.5(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C23 C22 C21 119.5(3) . . ?
C23 C22 C24 119.5(3) . . ?
C21 C22 C24 121.1(3) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.6(2) . . ?
C21 C20 H20 119.7 . . ?
C12 C17 H17 119.8 . . ?
C16 C17 C12 120.4(3) . . ?
C16 C17 H17 119.8 . . ?
C9 C8 H8 119.7 . . ?
C7 C8 C9 120.5(2) . . ?
C7 C8 H8 119.7 . . ?
C6 C1 H1B 119.6 . . ?
C2 C1 C6 120.8(3) . . ?
C2 C1 H1B 119.6 . . ?
C4 C3 H3 119.5 . . ?
C4 C3 C2 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
C22 C21 H21 120.1 . . ?
C20 C21 C22 119.8(3) . . ?
C20 C21 H21 120.1 . . ?
C1 C2 C3 120.0(3) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.1(3) . . ?
C8 C7 H7 119.5 . . ?
F1 C24 C22 115.5(3) . . ?
F1 C24 F3 101.0(4) . . ?
F2 C24 F1 105.5(4) . . ?
F2 C24 C22 116.2(4) . . ?
F2 C24 F3 103.4(4) . . ?
F3 C24 C22 113.6(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14 119.9 . . ?
C17 C16 H16 120.1 . . ?
C17 C16 C15 119.8(3) . . ?
C15 C16 H16 120.1 . . ?
C14 C15 C16 120.2(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.272
_oxdiff_exptl_absorpt_empirical_full_min 0.642
####################################################################### 
# 
# 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_191227b
_database_code_depnum_ccdc_archive 'CCDC 1974649'
loop_
_audit_author_name
_audit_author_address
'HONGYIN GAO'
;Shandong University
China
;
_audit_update_record             
;
2019-12-30 deposited with the CCDC.	2020-06-10 downloaded from the CCDC.
;
_audit_creation_date             2019-12-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H15 Br2 N O2'
_chemical_formula_sum            'C23 H15 Br2 N O2'
_chemical_formula_weight         497.18
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     BrCNO
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'
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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   8.98050(10)
_cell_length_b                   11.7542(2)
_cell_length_c                   18.4054(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1942.85(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10629
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.6820
_cell_measurement_theta_min      4.4240
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.447
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18763
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.064
_diffrn_reflns_theta_min         4.463
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -118.00 -65.00   1.00    0.12    --  -48.45-137.00 -58.00   53
  2  ω   -102.00 -67.00   1.00    0.12    --  -48.45-132.00 118.00   35
  3  ω    -92.00 -39.00   1.00    0.12    --  -48.45 137.00   4.00   53
  4  ω     43.00  68.00   1.00    0.12    --   48.45-132.00 118.00   25
  5  ω     46.00  71.00   1.00    0.12    --   48.45-137.00 -58.00   25
  6  ω   -101.00 -75.00   1.00    0.60    --  -86.25-137.00 -58.00   26
  7  ω    -97.00 -17.00   1.00    0.60    --  -86.25 132.00-171.00   80
  8  ω     72.00  98.00   1.00    0.60    --  106.49-137.00 -58.00   26
  9  ω     35.00  88.00   1.00    0.60    --  106.49-132.00 118.00   53
 10  ω     92.00 170.00   1.00    0.60    --  106.49 137.00   4.00   78
 11  ω     91.00 176.00   1.00    0.60    --  106.49 132.00-171.00   85
 12  ω     91.00 122.00   1.00    0.60    --  106.49-132.00 118.00   31
 13  ω    -61.00  26.00   1.00    0.12    --  -48.45  19.00  30.00   87
 14  ω    -49.00 -22.00   1.00    0.12    --  -48.45 132.00-171.00   27
 15  ω     27.00 120.00   1.00    0.12    --   48.45  77.00 -90.00   93
 16  ω   -158.00 -74.00   1.00    0.60    --  -86.25 -38.00 -60.00   84
 17  ω     34.00 106.00   1.00    0.60    --  106.49 -99.00 -30.00   72
 18  ω     92.00 177.00   1.00    0.60    --  106.49 125.00-120.00   85
 19  ω     34.00  64.00   1.00    0.60    --  106.49 -38.00-120.00   30
 20  ω    139.00 175.00   1.00    0.60    --  106.49 125.00 120.00   36
 21  ω     98.00 134.00   1.00    0.60    --  106.49 125.00 120.00   36
 22  ω     36.00 101.00   1.00    0.60    --  106.49 -99.00-150.00   65
 23  ω     76.00 118.00   1.00    0.60    --  106.49 -38.00-120.00   42
 24  ω     84.00 178.00   1.00    0.60    --  106.49  77.00  90.00   94
 25  ω     34.00 120.00   1.00    0.60    --  106.49 -38.00  60.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0240420000
_diffrn_orient_matrix_UB_12      0.1162621000
_diffrn_orient_matrix_UB_13      0.0367600000
_diffrn_orient_matrix_UB_21      -0.0410298000
_diffrn_orient_matrix_UB_22      -0.0604601000
_diffrn_orient_matrix_UB_23      0.0715415000
_diffrn_orient_matrix_UB_31      0.1648358000
_diffrn_orient_matrix_UB_32      0.0019251000
_diffrn_orient_matrix_UB_33      0.0231566000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3194
_reflns_number_total             3460
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)'
_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         0.361
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Flack x determined using 1286 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.083(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3460
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0313
_refine_ls_restrained_S_all      1.062
_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)+(0.0343P)²+1.1482P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0832
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C14(H14), C15(H15),
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.77096(7) 0.23761(5) 0.47575(3) 0.05340(19) Uani 1 1 d . . . . .
Br2 Br 0.36157(8) -0.07385(6) 0.59142(5) 0.0680(2) Uani 1 1 d . . . . .
O1 O 0.6494(5) 0.2198(4) 0.7522(2) 0.0525(10) Uani 1 1 d . . . . .
H1 H 0.5943 0.1895 0.7820 0.079 Uiso 1 1 calc GR . . . .
O2 O 0.5297(4) 0.5958(4) 0.6533(2) 0.0524(10) Uani 1 1 d . . . . .
N1 N 0.6153(5) 0.4524(4) 0.5832(3) 0.0402(10) Uani 1 1 d . . . . .
H1A H 0.5889 0.4042 0.5505 0.048 Uiso 1 1 calc R . . . .
C1 C 0.4214(5) 0.5750(4) 0.5358(3) 0.0384(11) Uani 1 1 d . . . . .
C2 C 0.5229(5) 0.5413(4) 0.5967(3) 0.0364(11) Uani 1 1 d . . . . .
C3 C 0.6711(6) 0.1782(4) 0.5581(3) 0.0360(11) Uani 1 1 d . . . . .
C4 C 1.0385(6) 0.4054(5) 0.6779(3) 0.0444(13) Uani 1 1 d . . . . .
C5 C 0.5731(6) 0.0897(5) 0.5455(3) 0.0419(12) Uani 1 1 d . . . . .
H5 H 0.5568 0.0611 0.4991 0.050 Uiso 1 1 calc R . . . .
C6 C 0.9841(7) 0.5142(5) 0.6601(4) 0.0520(15) Uani 1 1 d . . . . .
H6 H 1.0437 0.5777 0.6682 0.062 Uiso 1 1 calc R . . . .
C7 C 0.8470(7) 0.5281(5) 0.6314(3) 0.0450(13) Uani 1 1 d . . . . .
H7 H 0.8142 0.6007 0.6192 0.054 Uiso 1 1 calc R . . . .
C8 C 0.6226(6) 0.1753(5) 0.6849(3) 0.0400(12) Uani 1 1 d . . . . .
C9 C 0.6979(5) 0.2255(4) 0.6263(2) 0.0344(10) Uani 1 1 d . . . . .
C10 C 0.7528(5) 0.4334(4) 0.6196(3) 0.0359(10) Uani 1 1 d . . . . .
C11 C 0.5242(6) 0.0853(5) 0.6746(3) 0.0420(12) Uani 1 1 d . . . . .
H11 H 0.4754 0.0524 0.7139 0.050 Uiso 1 1 calc R . . . .
C12 C 0.2948(7) 0.6390(5) 0.5530(4) 0.0491(14) Uani 1 1 d . . . . .
H12 H 0.2702 0.6524 0.6014 0.059 Uiso 1 1 calc R . . . .
C13 C 0.9458(6) 0.3088(5) 0.6662(3) 0.0376(11) Uani 1 1 d . . . . .
C14 C 0.4561(7) 0.5556(5) 0.4644(3) 0.0497(14) Uani 1 1 d . . . . .
H14 H 0.5384 0.5113 0.4526 0.060 Uiso 1 1 calc R . . . .
C15 C 0.2454(9) 0.6645(5) 0.4265(4) 0.0662(19) Uani 1 1 d . . . . .
H15 H 0.1870 0.6952 0.3896 0.079 Uiso 1 1 calc R . . . .
C16 C 0.5005(6) 0.0460(5) 0.6056(3) 0.0434(13) Uani 1 1 d . . . . .
C17 C 0.7985(6) 0.3250(4) 0.6373(3) 0.0341(10) Uani 1 1 d . . . . .
C18 C 1.1839(6) 0.3888(7) 0.7064(4) 0.0589(17) Uani 1 1 d . . . . .
H18 H 1.2444 0.4514 0.7158 0.071 Uiso 1 1 calc R . . . .
C19 C 1.2351(7) 0.2825(7) 0.7199(3) 0.0637(18) Uani 1 1 d . . . . .
H19 H 1.3314 0.2726 0.7374 0.076 Uiso 1 1 calc R . . . .
C20 C 0.3690(8) 0.6020(6) 0.4096(4) 0.0645(18) Uani 1 1 d . . . . .
H20 H 0.3947 0.5904 0.3612 0.077 Uiso 1 1 calc R . . . .
C21 C 1.1453(8) 0.1882(7) 0.7080(4) 0.0621(18) Uani 1 1 d . . . . .
H21 H 1.1821 0.1159 0.7181 0.075 Uiso 1 1 calc R . . . .
C22 C 1.0036(7) 0.2000(6) 0.6818(3) 0.0501(14) Uani 1 1 d . . . . .
H22 H 0.9451 0.1358 0.6741 0.060 Uiso 1 1 calc R . . . .
C23 C 0.2071(8) 0.6820(5) 0.4986(5) 0.065(2) Uani 1 1 d . . . . .
H23 H 0.1217 0.7230 0.5100 0.078 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 C3 1.895(5) . ?
Br2 C16 1.899(5) . ?
O1 H1 0.8200 . ?
O1 C8 1.366(7) . ?
O2 C2 1.225(7) . ?
N1 H1A 0.8600 . ?
N1 C2 1.358(7) . ?
N1 C10 1.422(7) . ?
C1 C2 1.497(7) . ?
C1 C12 1.400(8) . ?
C1 C14 1.370(8) . ?
C3 C5 1.383(7) . ?
C3 C9 1.393(7) . ?
C4 C6 1.409(9) . ?
C4 C13 1.424(8) . ?
C4 C18 1.421(8) . ?
C5 H5 0.9300 . ?
C5 C16 1.383(8) . ?
C6 H6 0.9300 . ?
C6 C7 1.349(9) . ?
C7 H7 0.9300 . ?
C7 C10 1.415(8) . ?
C8 C9 1.404(7) . ?
C8 C11 1.391(8) . ?
C9 C17 1.491(7) . ?
C10 C17 1.378(7) . ?
C11 H11 0.9300 . ?
C11 C16 1.369(8) . ?
C12 H12 0.9300 . ?
C12 C23 1.371(9) . ?
C13 C17 1.438(7) . ?
C13 C22 1.410(8) . ?
C14 H14 0.9300 . ?
C14 C20 1.388(9) . ?
C15 H15 0.9300 . ?
C15 C20 1.367(11) . ?
C15 C23 1.386(11) . ?
C18 H18 0.9300 . ?
C18 C19 1.354(10) . ?
C19 H19 0.9300 . ?
C19 C21 1.388(11) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C21 C22 1.368(9) . ?
C22 H22 0.9300 . ?
C23 H23 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
C8 O1 H1 109.5 . . ?
C2 N1 H1A 117.8 . . ?
C2 N1 C10 124.4(4) . . ?
C10 N1 H1A 117.8 . . ?
C12 C1 C2 117.9(5) . . ?
C14 C1 C2 122.3(5) . . ?
C14 C1 C12 119.4(5) . . ?
O2 C2 N1 121.8(5) . . ?
O2 C2 C1 121.9(5) . . ?
N1 C2 C1 116.1(5) . . ?
C5 C3 Br1 116.4(4) . . ?
C5 C3 C9 124.2(5) . . ?
C9 C3 Br1 119.4(4) . . ?
C6 C4 C13 119.1(5) . . ?
C6 C4 C18 122.0(6) . . ?
C18 C4 C13 119.0(6) . . ?
C3 C5 H5 121.8 . . ?
C3 C5 C16 116.4(5) . . ?
C16 C5 H5 121.8 . . ?
C4 C6 H6 119.4 . . ?
C7 C6 C4 121.2(6) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C10 120.7(6) . . ?
C10 C7 H7 119.7 . . ?
O1 C8 C9 116.8(5) . . ?
O1 C8 C11 121.8(5) . . ?
C11 C8 C9 121.4(5) . . ?
C3 C9 C8 116.2(5) . . ?
C3 C9 C17 122.7(4) . . ?
C8 C9 C17 121.1(4) . . ?
C7 C10 N1 117.9(5) . . ?
C17 C10 N1 121.0(4) . . ?
C17 C10 C7 120.9(5) . . ?
C8 C11 H11 120.6 . . ?
C16 C11 C8 118.8(5) . . ?
C16 C11 H11 120.6 . . ?
C1 C12 H12 120.0 . . ?
C23 C12 C1 119.9(6) . . ?
C23 C12 H12 120.0 . . ?
C4 C13 C17 119.2(5) . . ?
C22 C13 C4 118.5(5) . . ?
C22 C13 C17 122.3(5) . . ?
C1 C14 H14 119.9 . . ?
C1 C14 C20 120.3(6) . . ?
C20 C14 H14 119.9 . . ?
C20 C15 H15 120.0 . . ?
C20 C15 C23 120.0(6) . . ?
C23 C15 H15 120.0 . . ?
C5 C16 Br2 118.4(4) . . ?
C11 C16 Br2 118.7(4) . . ?
C11 C16 C5 122.9(5) . . ?
C10 C17 C9 120.8(4) . . ?
C10 C17 C13 118.9(5) . . ?
C13 C17 C9 120.3(5) . . ?
C4 C18 H18 119.8 . . ?
C19 C18 C4 120.4(7) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 119.6 . . ?
C18 C19 C21 120.7(6) . . ?
C21 C19 H19 119.6 . . ?
C14 C20 H20 119.9 . . ?
C15 C20 C14 120.2(7) . . ?
C15 C20 H20 119.9 . . ?
C19 C21 H21 119.5 . . ?
C22 C21 C19 121.0(7) . . ?
C22 C21 H21 119.5 . . ?
C13 C22 H22 119.8 . . ?
C21 C22 C13 120.4(6) . . ?
C21 C22 H22 119.8 . . ?
C12 C23 C15 120.1(7) . . ?
C12 C23 H23 119.9 . . ?
C15 C23 H23 119.9 . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.500
_oxdiff_exptl_absorpt_empirical_full_min 0.740
