# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 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_1-BrisoQ
_database_code_depnum_ccdc_archive 'CCDC 2101809'
loop_
_audit_author_name
_audit_author_address
'Hajin Lee'
;Korea Basic Science Institute
South Korea
;
_audit_update_record             
;
2021-08-06 deposited with the CCDC.	2021-10-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 N O'
_chemical_formula_sum            'C19 H19 N O'
_chemical_formula_weight         277.35

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.660(4)
_cell_length_b                   14.860(8)
_cell_length_c                   10.952(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.555(17)
_cell_angle_gamma                90
_cell_volume                     1534.5(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    2640
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      25.09

_exptl_crystal_description       block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.051
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5411
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'PHOTON III M14'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14412
_diffrn_reflns_av_unetI/netI     0.0931
_diffrn_reflns_av_R_equivalents  0.0953
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.347
_diffrn_reflns_theta_max         28.347
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3793
_reflns_number_gt                1901
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1024P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3793
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1434
_refine_ls_R_factor_gt           0.0682
_refine_ls_wR_factor_ref         0.2149
_refine_ls_wR_factor_gt          0.1700
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_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 0.6573(2) 0.80620(15) 0.3616(2) 0.0397(5) Uani 1 1 d . . . . .
C2 C 0.5451(2) 0.74682(15) 0.3316(2) 0.0434(6) Uani 1 1 d . . . . .
H2 H 0.4514 0.7683 0.3123 0.052 Uiso 1 1 calc R U . . .
C3 C 0.5718(2) 0.65517(16) 0.3301(2) 0.0440(6) Uani 1 1 d . . . . .
H3 H 0.4947 0.6153 0.3101 0.053 Uiso 1 1 calc R U . . .
C4 C 0.7084(2) 0.62014(16) 0.3569(2) 0.0408(6) Uani 1 1 d . . . . .
C5 C 0.8180(2) 0.68196(18) 0.3851(2) 0.0521(7) Uani 1 1 d . . . . .
H5 H 0.9120 0.6608 0.4028 0.062 Uiso 1 1 calc R U . . .
C6 C 0.7946(3) 0.77318(17) 0.3882(3) 0.0521(7) Uani 1 1 d . . . . .
H6 H 0.8718 0.8130 0.4083 0.062 Uiso 1 1 calc R U . . .
O1 O 0.64388(18) 0.89756(11) 0.36858(16) 0.0535(5) Uani 1 1 d . . . . .
C7 C 0.5045(3) 0.93414(18) 0.3415(3) 0.0673(8) Uani 1 1 d . . . . .
H7A H 0.4570 0.9177 0.2570 0.101 Uiso 1 1 calc R U . . .
H7B H 0.5098 0.9992 0.3486 0.101 Uiso 1 1 calc R U . . .
H7C H 0.4517 0.9105 0.4003 0.101 Uiso 1 1 calc R U . . .
C8 C 0.7358(3) 0.52080(15) 0.3552(2) 0.0479(6) Uani 1 1 d . . . . .
H8A H 0.8245 0.5110 0.3275 0.057 Uiso 1 1 calc R U . . .
H8B H 0.6593 0.4927 0.2934 0.057 Uiso 1 1 calc R U . . .
C9 C 0.7462(3) 0.47402(15) 0.4801(2) 0.0483(6) Uani 1 1 d . . . . .
H9A H 0.8261 0.4991 0.5413 0.058 Uiso 1 1 calc R U . . .
H9B H 0.6594 0.4855 0.5102 0.058 Uiso 1 1 calc R U . . .
C10 C 0.7665(3) 0.37355(15) 0.47005(19) 0.0455(6) Uani 1 1 d . . . . .
H10A H 0.6807 0.3484 0.4163 0.055 Uiso 1 1 calc R U . . .
H10B H 0.8450 0.3633 0.4281 0.055 Uiso 1 1 calc R U . . .
C11 C 0.7969(2) 0.32203(15) 0.59155(19) 0.0379(5) Uani 1 1 d . . . . .
N1 N 0.8054(2) 0.36907(13) 0.69543(17) 0.0459(5) Uani 1 1 d . . . . .
C12 C 0.8348(3) 0.32356(17) 0.8068(2) 0.0522(7) Uani 1 1 d . . . . .
H12 H 0.8400 0.3570 0.8805 0.063 Uiso 1 1 calc R U . . .
C13 C 0.8571(3) 0.23380(17) 0.8181(2) 0.0512(7) Uani 1 1 d . . . . .
H13 H 0.8774 0.2065 0.8974 0.061 Uiso 1 1 calc R U . . .
C14 C 0.8491(2) 0.18183(16) 0.7088(2) 0.0406(6) Uani 1 1 d . . . . .
C15 C 0.8177(2) 0.22670(15) 0.59166(19) 0.0366(5) Uani 1 1 d . . . . .
C16 C 0.8081(2) 0.17516(16) 0.4814(2) 0.0448(6) Uani 1 1 d . . . . .
H16 H 0.7873 0.2039 0.4031 0.054 Uiso 1 1 calc R U . . .
C17 C 0.8286(3) 0.08445(16) 0.4873(2) 0.0502(6) Uani 1 1 d . . . . .
H17 H 0.8223 0.0513 0.4132 0.060 Uiso 1 1 calc R U . . .
C18 C 0.8593(3) 0.04004(17) 0.6034(2) 0.0529(7) Uani 1 1 d . . . . .
H18 H 0.8730 -0.0226 0.6065 0.064 Uiso 1 1 calc R U . . .
C19 C 0.8692(3) 0.08722(17) 0.7110(2) 0.0496(6) Uani 1 1 d . . . . .
H19 H 0.8896 0.0568 0.7881 0.060 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.368(3) . ?
C1 C2 1.381(3) . ?
C1 C6 1.384(3) . ?
C2 C3 1.387(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.389(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.385(3) . ?
C4 C8 1.501(3) . ?
C5 C6 1.376(3) . ?
C5 H5 0.9400 . ?
C6 H6 0.9400 . ?
O1 C7 1.422(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 H7C 0.9700 . ?
C8 C9 1.518(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 C10 1.513(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 C11 1.508(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 N1 1.323(3) . ?
C11 C15 1.431(3) . ?
N1 C12 1.369(3) . ?
C12 C13 1.352(3) . ?
C12 H12 0.9400 . ?
C13 C14 1.413(3) . ?
C13 H13 0.9400 . ?
C14 C19 1.419(3) . ?
C14 C15 1.419(3) . ?
C15 C16 1.416(3) . ?
C16 C17 1.362(3) . ?
C16 H16 0.9400 . ?
C17 C18 1.406(3) . ?
C17 H17 0.9400 . ?
C18 C19 1.356(3) . ?
C18 H18 0.9400 . ?
C19 H19 0.9400 . ?

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
O1 C1 C2 124.6(2) . . ?
O1 C1 C6 116.0(2) . . ?
C2 C1 C6 119.3(2) . . ?
C1 C2 C3 119.5(2) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C2 C3 C4 122.4(2) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C5 C4 C3 116.3(2) . . ?
C5 C4 C8 121.8(2) . . ?
C3 C4 C8 121.9(2) . . ?
C6 C5 C4 122.5(2) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C5 C6 C1 119.9(2) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C1 O1 C7 117.7(2) . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 C9 114.59(19) . . ?
C4 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
C4 C8 H8B 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C8 111.74(19) . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 116.13(19) . . ?
C11 C10 H10A 108.3 . . ?
C9 C10 H10A 108.3 . . ?
C11 C10 H10B 108.3 . . ?
C9 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
N1 C11 C15 122.7(2) . . ?
N1 C11 C10 117.0(2) . . ?
C15 C11 C10 120.26(19) . . ?
C11 N1 C12 117.8(2) . . ?
C13 C12 N1 124.5(2) . . ?
C13 C12 H12 117.7 . . ?
N1 C12 H12 117.7 . . ?
C12 C13 C14 118.9(2) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C13 C14 C19 123.1(2) . . ?
C13 C14 C15 118.1(2) . . ?
C19 C14 C15 118.8(2) . . ?
C16 C15 C14 118.6(2) . . ?
C16 C15 C11 123.5(2) . . ?
C14 C15 C11 117.9(2) . . ?
C17 C16 C15 120.9(2) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 120.5(2) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 120.3(2) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C14 120.9(2) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?

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
O1 C1 C2 C3 -178.6(2) . . . . ?
C6 C1 C2 C3 0.8(3) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C2 C3 C4 C8 179.9(2) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C8 C4 C5 C6 -179.4(2) . . . . ?
C4 C5 C6 C1 -0.5(4) . . . . ?
O1 C1 C6 C5 179.1(2) . . . . ?
C2 C1 C6 C5 -0.4(4) . . . . ?
C2 C1 O1 C7 -0.8(3) . . . . ?
C6 C1 O1 C7 179.8(2) . . . . ?
C5 C4 C8 C9 89.0(3) . . . . ?
C3 C4 C8 C9 -91.2(3) . . . . ?
C4 C8 C9 C10 177.2(2) . . . . ?
C8 C9 C10 C11 172.4(2) . . . . ?
C9 C10 C11 N1 -1.1(3) . . . . ?
C9 C10 C11 C15 180.0(2) . . . . ?
C15 C11 N1 C12 -0.2(3) . . . . ?
C10 C11 N1 C12 -179.1(2) . . . . ?
C11 N1 C12 C13 0.6(4) . . . . ?
N1 C12 C13 C14 -0.4(4) . . . . ?
C12 C13 C14 C19 -179.3(2) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C13 C14 C15 C16 -179.4(2) . . . . ?
C19 C14 C15 C16 -0.2(3) . . . . ?
C13 C14 C15 C11 0.4(3) . . . . ?
C19 C14 C15 C11 179.6(2) . . . . ?
N1 C11 C15 C16 179.6(2) . . . . ?
C10 C11 C15 C16 -1.6(3) . . . . ?
N1 C11 C15 C14 -0.2(3) . . . . ?
C10 C11 C15 C14 178.6(2) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C11 C15 C16 C17 -179.8(2) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C16 C17 C18 C19 -0.2(4) . . . . ?
C17 C18 C19 C14 -0.1(4) . . . . ?
C13 C14 C19 C18 179.4(2) . . . . ?
C15 C14 C19 C18 0.3(3) . . . . ?

_refine_diff_density_max         0.352
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.115

