# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_210601-pl02-pwy
_database_code_depnum_ccdc_archive 'CCDC 2159660'
loop_
_audit_author_name
_audit_author_address
'Xiaotong Li'
;Northeast Normal University
China
;
_audit_update_record             
;
2022-03-17 deposited with the CCDC.	2023-01-12 downloaded from the CCDC.
;
_audit_creation_date             2021-09-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
2-(4-(dimethylamino)-2-isopropylbenzyl)-4-(trifluoromethyl)naphthalen-1-ol
_chemical_formula_moiety         '0.5(C23 H24 F3 N O)'
_chemical_formula_sum            'C11 H10 F N O'
_chemical_formula_weight         191.20
_chemical_melting_point          389-390
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'
F F 0.0171 0.0103 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8092(7)
_cell_length_b                   9.8034(8)
_cell_length_c                   12.4843(10)
_cell_angle_alpha                71.412(8)
_cell_angle_beta                 74.369(7)
_cell_angle_gamma                85.988(7)
_cell_volume                     983.96(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1742
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3960
_cell_measurement_theta_min      4.1580
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             400
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.833
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7367
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.430
_diffrn_reflns_theta_min         3.557
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2375
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.833
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00  15.00   1.00    5.18    --   -9.92 -57.00 -90.00   86
  2  ω    -59.00  31.00   1.00    5.18    --   11.09 -57.00  60.00   90
  3  ω    -11.00  78.00   1.00    5.18    --   11.09  57.00-150.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0533208000
_diffrn_orient_matrix_UB_12      0.0547306000
_diffrn_orient_matrix_UB_13      0.0107311000
_diffrn_orient_matrix_UB_21      -0.0111776000
_diffrn_orient_matrix_UB_22      -0.0327116000
_diffrn_orient_matrix_UB_23      0.0611459000
_diffrn_orient_matrix_UB_31      0.0634415000
_diffrn_orient_matrix_UB_32      0.0419912000
_diffrn_orient_matrix_UB_33      -0.0016033000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3012
_reflns_number_total             4548
_reflns_odcompleteness_completeness 99.23
_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 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_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 (Sheldrick, 2008)'
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4548
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0667
_refine_ls_restrained_S_all      1.048
_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)+(0.0970P)²+0.3420P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1749
_refine_ls_wR_factor_ref         0.2078
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C16(H16), C17(H17), C18(H18), C20(H20)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.96139(18) 0.71476(18) 0.08547(13) 0.0478(4) Uani 1 1 d . . . . .
H1 H 0.8748 0.7526 0.0916 0.072 Uiso 1 1 calc GR . . . .
N1 N 1.6481(2) 0.7803(2) 0.19635(16) 0.0437(5) Uani 1 1 d . . . . .
C3 C 0.9957(2) 0.8570(2) -0.11849(18) 0.0375(5) Uani 1 1 d . . . . .
C4 C 1.0347(2) 0.7378(2) -0.02923(18) 0.0366(5) Uani 1 1 d . . . . .
C5 C 1.5373(2) 0.7122(2) 0.16227(18) 0.0362(5) Uani 1 1 d . . . . .
C6 C 1.3195(2) 0.5907(2) 0.08743(18) 0.0340(4) Uani 1 1 d . . . . .
C7 C 1.4246(2) 0.7006(2) 0.01138(18) 0.0389(5) Uani 1 1 d . . . . .
H7 H 1.4229 0.7350 -0.0668 0.047 Uiso 1 1 calc R . . . .
C8 C 1.4350(2) 0.6007(2) 0.23922(18) 0.0399(5) Uani 1 1 d . . . . .
H8 H 1.4388 0.5662 0.3170 0.048 Uiso 1 1 calc R . . . .
C9 C 1.2057(3) 0.5309(2) 0.0401(2) 0.0412(5) Uani 1 1 d . . . . .
H9A H 1.2568 0.4551 0.0097 0.049 Uiso 1 1 calc R . . . .
H9B H 1.1144 0.4889 0.1037 0.049 Uiso 1 1 calc R . . . .
C10 C 1.5310(2) 0.7605(2) 0.04720(19) 0.0406(5) Uani 1 1 d . . . . .
H10 H 1.5990 0.8341 -0.0066 0.049 Uiso 1 1 calc R . . . .
C11 C 1.2234(3) 0.6610(2) -0.1736(2) 0.0435(5) Uani 1 1 d . . . . .
H11 H 1.3009 0.5965 -0.1920 0.052 Uiso 1 1 calc R . . . .
C12 C 1.1518(2) 0.6449(2) -0.05555(19) 0.0379(5) Uani 1 1 d . . . . .
C13 C 1.3268(2) 0.5386(2) 0.20413(18) 0.0385(5) Uani 1 1 d . . . . .
C14 C 1.0697(3) 0.8719(2) -0.23790(19) 0.0414(5) Uani 1 1 d . . . . .
C15 C 1.1841(3) 0.7679(3) -0.2632(2) 0.0455(5) Uani 1 1 d . . . . .
C16 C 0.8906(3) 0.9641(2) -0.0911(2) 0.0449(5) Uani 1 1 d . . . . .
H16 H 0.8445 0.9567 -0.0131 0.054 Uiso 1 1 calc R . . . .
C17 C 1.0277(3) 0.9907(3) -0.3244(2) 0.0545(6) Uani 1 1 d . . . . .
H17 H 1.0722 1.0010 -0.4032 0.065 Uiso 1 1 calc R . . . .
C18 C 0.8555(3) 1.0780(3) -0.1767(2) 0.0557(7) Uani 1 1 d . . . . .
H18 H 0.7866 1.1478 -0.1572 0.067 Uiso 1 1 calc R . . . .
F3 F 1.3479(3) 0.8992(2) -0.44530(17) 0.1024(7) Uani 1 1 d . . . . .
C20 C 0.9236(3) 1.0895(3) -0.2941(3) 0.0603(7) Uani 1 1 d . . . . .
H20 H 0.8972 1.1660 -0.3525 0.072 Uiso 1 1 calc R . . . .
F2 F 1.1648(3) 0.7729(3) -0.44883(17) 0.1073(8) Uani 1 1 d . . . . .
F1 F 1.3660(3) 0.6718(2) -0.39575(16) 0.0967(7) Uani 1 1 d . . . . .
C23 C 1.2185(3) 0.4159(3) 0.2936(2) 0.0541(6) Uani 1 1 d . . . . .
H23 H 1.1173 0.4253 0.2735 0.065 Uiso 1 1 calc R . . . .
C24 C 1.6780(3) 0.7015(3) 0.3097(2) 0.0656(8) Uani 1 1 d . . . . .
H24A H 1.5842 0.6993 0.3711 0.098 Uiso 1 1 calc GR . . . .
H24B H 1.7618 0.7486 0.3209 0.098 Uiso 1 1 calc GR . . . .
H24C H 1.7077 0.6048 0.3114 0.098 Uiso 1 1 calc GR . . . .
C25 C 1.6043(4) 0.9293(3) 0.1911(3) 0.0656(8) Uani 1 1 d . . . . .
H25A H 1.5885 0.9805 0.1154 0.098 Uiso 1 1 calc GR . . . .
H25B H 1.6871 0.9757 0.2040 0.098 Uiso 1 1 calc GR . . . .
H25C H 1.5086 0.9291 0.2504 0.098 Uiso 1 1 calc GR . . . .
C26 C 1.2652(4) 0.7776(4) -0.3864(3) 0.0679(8) Uani 1 1 d . . . . .
C27 C 1.1862(6) 0.4199(5) 0.4190(3) 0.1171(16) Uani 1 1 d . . . . .
H27A H 1.2802 0.3957 0.4454 0.176 Uiso 1 1 calc GR . . . .
H27B H 1.1037 0.3517 0.4690 0.176 Uiso 1 1 calc GR . . . .
H27C H 1.1543 0.5147 0.4214 0.176 Uiso 1 1 calc GR . . . .
C28 C 1.2830(5) 0.2742(3) 0.2879(4) 0.1044(14) Uani 1 1 d . . . . .
H28A H 1.3061 0.2724 0.2087 0.157 Uiso 1 1 calc GR . . . .
H28B H 1.2069 0.1998 0.3375 0.157 Uiso 1 1 calc GR . . . .
H28C H 1.3779 0.2584 0.3137 0.157 Uiso 1 1 calc GR . . . .


_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 C4 1.354(3) . ?
N1 C5 1.441(3) . ?
N1 C24 1.465(3) . ?
N1 C25 1.470(3) . ?
C3 C4 1.430(3) . ?
C3 C14 1.421(3) . ?
C3 C16 1.414(3) . ?
C4 C12 1.371(3) . ?
C5 C8 1.390(3) . ?
C5 C10 1.377(3) . ?
C6 C7 1.390(3) . ?
C6 C9 1.523(3) . ?
C6 C13 1.400(3) . ?
C7 C10 1.376(3) . ?
C8 C13 1.395(3) . ?
C9 C12 1.510(3) . ?
C11 C12 1.400(3) . ?
C11 C15 1.371(3) . ?
C13 C23 1.528(3) . ?
C14 C15 1.429(3) . ?
C14 C17 1.419(3) . ?
C15 C26 1.487(4) . ?
C16 C18 1.361(3) . ?
C17 C20 1.359(4) . ?
C18 C20 1.397(4) . ?
F3 C26 1.329(4) . ?
F2 C26 1.339(4) . ?
F1 C26 1.330(4) . ?
C23 C27 1.527(5) . ?
C23 C28 1.479(4) . ?

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
C5 N1 C24 115.28(18) . . ?
C5 N1 C25 111.50(18) . . ?
C24 N1 C25 110.5(2) . . ?
C14 C3 C4 119.2(2) . . ?
C16 C3 C4 121.8(2) . . ?
C16 C3 C14 118.97(19) . . ?
O1 C4 C3 121.44(19) . . ?
O1 C4 C12 116.99(18) . . ?
C12 C4 C3 121.5(2) . . ?
C8 C5 N1 123.73(19) . . ?
C10 C5 N1 118.42(17) . . ?
C10 C5 C8 117.85(19) . . ?
C7 C6 C9 119.06(18) . . ?
C7 C6 C13 117.55(18) . . ?
C13 C6 C9 123.38(17) . . ?
C10 C7 C6 122.65(19) . . ?
C5 C8 C13 122.44(19) . . ?
C12 C9 C6 112.47(16) . . ?
C7 C10 C5 120.35(18) . . ?
C15 C11 C12 122.7(2) . . ?
C4 C12 C9 120.9(2) . . ?
C4 C12 C11 118.25(19) . . ?
C11 C12 C9 120.8(2) . . ?
C6 C13 C23 121.34(19) . . ?
C8 C13 C6 119.13(18) . . ?
C8 C13 C23 119.52(19) . . ?
C3 C14 C15 117.96(19) . . ?
C17 C14 C3 117.9(2) . . ?
C17 C14 C15 124.1(2) . . ?
C11 C15 C14 120.1(2) . . ?
C11 C15 C26 119.5(2) . . ?
C14 C15 C26 120.4(2) . . ?
C18 C16 C3 121.3(2) . . ?
C20 C17 C14 121.1(2) . . ?
C16 C18 C20 119.7(2) . . ?
C17 C20 C18 121.0(2) . . ?
C27 C23 C13 113.2(2) . . ?
C28 C23 C13 111.2(2) . . ?
C28 C23 C27 109.3(3) . . ?
F3 C26 C15 113.2(3) . . ?
F3 C26 F2 105.2(3) . . ?
F3 C26 F1 105.8(3) . . ?
F2 C26 C15 112.8(2) . . ?
F1 C26 C15 113.4(2) . . ?
F1 C26 F2 105.8(3) . . ?

_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 1.282
_oxdiff_exptl_absorpt_empirical_full_min 0.672
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Petroleum ether/Dichloromethane'
