# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_deh251
_database_code_depnum_ccdc_archive 'CCDC 2024461'
loop_
_audit_author_name
_audit_author_address
'David Herbert'
;University of Manitoba
Canada
;
_audit_update_record             
;
2020-08-20 deposited with the CCDC.	2020-11-26 downloaded from the CCDC.
;
_audit_creation_date             2019-02-12
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H8 F3 N O2'
_chemical_formula_sum            'C15 H8 F3 N O2'
_chemical_formula_weight         291.22
_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'
F F 0.0171 0.0103 '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'

_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                   7.6065(4)
_cell_length_b                   5.8376(3)
_cell_length_c                   27.3880(14)
_cell_angle_alpha                90
_cell_angle_beta                 96.766(2)
_cell_angle_gamma                90
_cell_volume                     1207.66(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8644
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.79
_cell_measurement_theta_min      2.88
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.941
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0648 before and 0.0595 after correction.
The Ratio of minimum to maximum transmission is 0.9195.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            36910
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.940
_diffrn_reflns_theta_min         2.712
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Quest ECO CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2030
_reflns_number_total             2889
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.290
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2889
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.027
_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)+(0.0438P)²+0.8104P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1108
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C10(H10), C11(H11), C13(H13), C14(H14)
;
_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
C1 C 0.6689(2) 0.4690(3) 0.91761(7) 0.0270(4) Uani 1 1 d . . . . .
H1 H 0.716985 0.453411 0.951063 0.032 Uiso 1 1 calc R . . . .
C2 C 0.5717(2) 0.6646(3) 0.90260(6) 0.0253(4) Uani 1 1 d . . . . .
H2 H 0.553659 0.780553 0.925838 0.030 Uiso 1 1 calc R . . . .
C3 C 0.5017(2) 0.6902(3) 0.85404(6) 0.0223(4) Uani 1 1 d . . . . .
H3 H 0.435995 0.823792 0.843891 0.027 Uiso 1 1 calc R . . . .
C4 C 0.5275(2) 0.5192(3) 0.81979(6) 0.0187(3) Uani 1 1 d . . . . .
C5 C 0.6239(2) 0.3255(3) 0.83595(6) 0.0203(4) Uani 1 1 d . . . . .
C6 C 0.6960(2) 0.2975(3) 0.88452(7) 0.0253(4) Uani 1 1 d . . . . .
H6 H 0.762188 0.164364 0.894725 0.030 Uiso 1 1 calc R . . . .
C7 C 0.4968(2) 0.3935(3) 0.73898(6) 0.0179(3) Uani 1 1 d . . . . .
C8 C 0.5926(2) 0.1764(3) 0.75432(6) 0.0194(4) Uani 1 1 d . . . . .
C9 C 0.4402(2) 0.4400(3) 0.68598(6) 0.0181(3) Uani 1 1 d . . . . .
C10 C 0.3505(2) 0.6460(3) 0.67388(6) 0.0206(4) Uani 1 1 d . . . . .
H10 H 0.325614 0.747325 0.699328 0.025 Uiso 1 1 calc R . . . .
C11 C 0.2981(2) 0.7033(3) 0.62543(6) 0.0224(4) Uani 1 1 d . . . . .
H11 H 0.236856 0.842957 0.617753 0.027 Uiso 1 1 calc R . . . .
C12 C 0.3348(2) 0.5571(3) 0.58789(6) 0.0220(4) Uani 1 1 d . . . . .
C13 C 0.4238(2) 0.3533(3) 0.59897(7) 0.0257(4) Uani 1 1 d . . . . .
H13 H 0.448894 0.253507 0.573286 0.031 Uiso 1 1 calc R . . . .
C14 C 0.4764(2) 0.2948(3) 0.64785(6) 0.0245(4) Uani 1 1 d . . . . .
H14 H 0.537505 0.154892 0.655310 0.029 Uiso 1 1 calc R . . . .
C15 C 0.2827(2) 0.6278(4) 0.53581(7) 0.0290(4) Uani 1 1 d . . . . .
F1 F 0.12006(17) 0.7140(3) 0.52835(4) 0.0582(5) Uani 1 1 d . . . . .
F2 F 0.38953(19) 0.7930(3) 0.52192(5) 0.0548(4) Uani 1 1 d . . . . .
F3 F 0.28996(19) 0.4595(2) 0.50347(4) 0.0515(4) Uani 1 1 d . . . . .
N1 N 0.46214(18) 0.5474(2) 0.77059(5) 0.0192(3) Uani 1 1 d . . . . .
O1 O 0.64906(15) 0.1532(2) 0.80329(4) 0.0217(3) Uani 1 1 d . . . . .
O2 O 0.61953(16) 0.0181(2) 0.72833(5) 0.0255(3) 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 C2 1.396(3) . ?
C1 C6 1.382(3) . ?
C2 C3 1.381(2) . ?
C3 C4 1.399(2) . ?
C4 C5 1.391(2) . ?
C4 N1 1.390(2) . ?
C5 C6 1.387(2) . ?
C5 O1 1.374(2) . ?
C7 C8 1.497(2) . ?
C7 C9 1.490(2) . ?
C7 N1 1.296(2) . ?
C8 O1 1.366(2) . ?
C8 O2 1.199(2) . ?
C9 C10 1.403(2) . ?
C9 C14 1.397(2) . ?
C10 C11 1.381(2) . ?
C11 C12 1.390(2) . ?
C12 C13 1.384(3) . ?
C12 C15 1.493(2) . ?
C13 C14 1.394(2) . ?
C15 F1 1.329(2) . ?
C15 F2 1.345(2) . ?
C15 F3 1.328(2) . ?

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 120.94(16) . . ?
C3 C2 C1 120.18(17) . . ?
C2 C3 C4 119.99(17) . . ?
C5 C4 C3 118.46(15) . . ?
N1 C4 C3 120.19(15) . . ?
N1 C4 C5 121.32(15) . . ?
C6 C5 C4 122.35(16) . . ?
O1 C5 C4 119.74(14) . . ?
O1 C5 C6 117.91(15) . . ?
C1 C6 C5 118.07(17) . . ?
C9 C7 C8 120.20(14) . . ?
N1 C7 C8 122.00(15) . . ?
N1 C7 C9 117.80(15) . . ?
O1 C8 C7 116.47(14) . . ?
O2 C8 C7 126.69(15) . . ?
O2 C8 O1 116.79(15) . . ?
C10 C9 C7 117.58(15) . . ?
C14 C9 C7 123.91(15) . . ?
C14 C9 C10 118.47(15) . . ?
C11 C10 C9 120.79(16) . . ?
C10 C11 C12 120.10(16) . . ?
C11 C12 C15 118.88(16) . . ?
C13 C12 C11 120.09(16) . . ?
C13 C12 C15 120.99(16) . . ?
C12 C13 C14 119.92(16) . . ?
C13 C14 C9 120.63(17) . . ?
F1 C15 C12 112.90(15) . . ?
F1 C15 F2 105.53(17) . . ?
F2 C15 C12 111.55(15) . . ?
F3 C15 C12 113.91(17) . . ?
F3 C15 F1 106.79(16) . . ?
F3 C15 F2 105.53(16) . . ?
C7 N1 C4 119.18(14) . . ?
C8 O1 C5 120.99(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_deh242_pl
_database_code_depnum_ccdc_archive 'CCDC 2024463'
loop_
_audit_author_name
_audit_author_address
'David Herbert'
;University of Manitoba
Canada
;
_audit_update_record             
;
2020-08-20 deposited with the CCDC.	2020-11-26 downloaded from the CCDC.
;
_audit_creation_date             2019-01-17
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H20 O3'
_chemical_formula_sum            'C16 H20 O3'
_chemical_formula_weight         260.32
_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'
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                   8.0826(3)
_cell_length_b                   22.3489(9)
_cell_length_c                   8.0949(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.167(2)
_cell_angle_gamma                90
_cell_volume                     1397.09(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9841
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      24.95
_cell_measurement_theta_min      2.64
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0718 before and 0.0601 after correction.
The Ratio of minimum to maximum transmission is 0.8718.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            31846
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.084
_diffrn_reflns_theta_max         25.084
_diffrn_reflns_theta_min         2.637
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Quest ECO CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1986
_reflns_number_total             2489
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2489
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0373
_refine_ls_restrained_S_all      1.044
_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)+(0.0361P)²+0.4601P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0874
_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
2.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_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
C1 C 0.85508(18) 0.36843(6) 0.37388(18) 0.0224(3) Uani 1 1 d . . . . .
C2 C 0.87038(18) 0.42963(7) 0.34978(19) 0.0270(3) Uani 1 1 d . . . . .
H2 H 0.775963 0.455441 0.346092 0.032 Uiso 1 1 calc R . . . .
C3 C 1.02193(19) 0.45302(7) 0.3312(2) 0.0297(4) Uani 1 1 d . . . . .
H3 H 1.031841 0.494814 0.314946 0.036 Uiso 1 1 calc R . . . .
C4 C 1.15939(19) 0.41542(7) 0.3364(2) 0.0288(4) Uani 1 1 d . . . . .
H4 H 1.264267 0.431540 0.325105 0.035 Uiso 1 1 calc R . . . .
C5 C 1.14467(19) 0.35448(7) 0.3580(2) 0.0275(3) Uani 1 1 d . . . . .
H5 H 1.238924 0.328838 0.359834 0.033 Uiso 1 1 calc R . . . .
C6 C 0.99340(18) 0.33069(6) 0.37703(18) 0.0256(3) Uani 1 1 d . . . . .
H6 H 0.983747 0.288816 0.392161 0.031 Uiso 1 1 calc R . . . .
C7 C 0.68867(18) 0.34608(7) 0.39092(18) 0.0248(3) Uani 1 1 d . . . . .
C8 C 0.67728(18) 0.28177(6) 0.45187(19) 0.0243(3) Uani 1 1 d . . . . .
C9 C 0.49026(18) 0.19691(6) 0.42019(19) 0.0250(3) Uani 1 1 d . . . . .
H9 H 0.551073 0.191683 0.546216 0.030 Uiso 1 1 calc R . . . .
C10 C 0.55361(19) 0.15025(7) 0.3189(2) 0.0285(4) Uani 1 1 d . . . . .
H10A H 0.680552 0.153960 0.342696 0.034 Uiso 1 1 calc R . . . .
H10B H 0.498846 0.156701 0.193658 0.034 Uiso 1 1 calc R . . . .
C11 C 0.50922(19) 0.08748(7) 0.3690(2) 0.0303(4) Uani 1 1 d . . . . .
H11 H 0.569250 0.081567 0.494922 0.036 Uiso 1 1 calc R . . . .
C12 C 0.31394(19) 0.08298(7) 0.3413(2) 0.0287(4) Uani 1 1 d . . . . .
H12A H 0.253039 0.086054 0.216100 0.034 Uiso 1 1 calc R . . . .
H12B H 0.287344 0.043226 0.381093 0.034 Uiso 1 1 calc R . . . .
C13 C 0.24554(18) 0.13126(7) 0.4367(2) 0.0265(3) Uani 1 1 d . . . . .
H13 H 0.299762 0.125095 0.563579 0.032 Uiso 1 1 calc R . . . .
C14 C 0.29716(18) 0.19337(6) 0.3904(2) 0.0278(3) Uani 1 1 d . . . . .
H14A H 0.236291 0.202054 0.267541 0.033 Uiso 1 1 calc R . . . .
H14B H 0.261814 0.223831 0.462119 0.033 Uiso 1 1 calc R . . . .
C15 C 0.5735(2) 0.03957(7) 0.2691(3) 0.0438(5) Uani 1 1 d . . . . .
H15A H 0.519683 0.045464 0.144771 0.066 Uiso 1 1 calc GR . . . .
H15B H 0.542462 -0.000055 0.302541 0.066 Uiso 1 1 calc GR . . . .
H15C H 0.699595 0.042451 0.295548 0.066 Uiso 1 1 calc GR . . . .
C16 C 0.04949(19) 0.12703(8) 0.3996(2) 0.0358(4) Uani 1 1 d . . . . .
H16A H -0.006681 0.133189 0.275822 0.054 Uiso 1 1 calc GR . . . .
H16B H 0.010288 0.157802 0.465768 0.054 Uiso 1 1 calc GR . . . .
H16C H 0.018957 0.087387 0.433362 0.054 Uiso 1 1 calc GR . . . .
O1 O 0.56086(13) 0.37742(5) 0.36615(15) 0.0352(3) Uani 1 1 d . . . . .
O2 O 0.78645(14) 0.25962(5) 0.56997(14) 0.0371(3) Uani 1 1 d . . . . .
O3 O 0.52702(12) 0.25708(4) 0.36564(13) 0.0265(3) 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 C2 1.392(2) . ?
C1 C6 1.395(2) . ?
C1 C7 1.4789(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.383(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.531(2) . ?
C7 O1 1.2147(17) . ?
C8 O2 1.1999(17) . ?
C8 O3 1.3290(16) . ?
C9 H9 1.0000 . ?
C9 C10 1.506(2) . ?
C9 C14 1.509(2) . ?
C9 O3 1.4728(17) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.532(2) . ?
C11 H11 1.0000 . ?
C11 C12 1.531(2) . ?
C11 C15 1.523(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.522(2) . ?
C13 H13 1.0000 . ?
C13 C14 1.528(2) . ?
C13 C16 1.526(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C2 C1 C6 119.53(13) . . ?
C2 C1 C7 117.75(13) . . ?
C6 C1 C7 122.71(13) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.38(13) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.82(14) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.24(14) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.32(14) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.72(13) . . ?
C5 C6 H6 120.1 . . ?
C1 C7 C8 119.33(12) . . ?
O1 C7 C1 122.85(13) . . ?
O1 C7 C8 117.73(13) . . ?
O2 C8 C7 122.96(13) . . ?
O2 C8 O3 126.18(13) . . ?
O3 C8 C7 110.67(11) . . ?
C10 C9 H9 109.3 . . ?
C10 C9 C14 112.23(12) . . ?
C14 C9 H9 109.3 . . ?
O3 C9 H9 109.3 . . ?
O3 C9 C10 109.75(11) . . ?
O3 C9 C14 106.90(11) . . ?
C9 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
C9 C10 C11 110.25(12) . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
C10 C11 H11 108.0 . . ?
C12 C11 C10 109.47(12) . . ?
C12 C11 H11 108.0 . . ?
C15 C11 C10 111.11(13) . . ?
C15 C11 H11 108.0 . . ?
C15 C11 C12 112.00(13) . . ?
C11 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 C11 113.10(12) . . ?
C13 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C12 C13 H13 108.0 . . ?
C12 C13 C14 110.68(12) . . ?
C12 C13 C16 111.57(12) . . ?
C14 C13 H13 108.0 . . ?
C16 C13 H13 108.0 . . ?
C16 C13 C14 110.54(12) . . ?
C9 C14 C13 110.67(12) . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C8 O3 C9 117.10(11) . . ?

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
C1 C2 C3 C4 0.1(2) . . . . ?
C1 C7 C8 O2 43.8(2) . . . . ?
C1 C7 C8 O3 -140.96(13) . . . . ?
C2 C1 C6 C5 0.7(2) . . . . ?
C2 C1 C7 C8 -168.30(13) . . . . ?
C2 C1 C7 O1 8.2(2) . . . . ?
C2 C3 C4 C5 0.8(2) . . . . ?
C3 C4 C5 C6 -0.9(2) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
C6 C1 C2 C3 -0.8(2) . . . . ?
C6 C1 C7 C8 13.2(2) . . . . ?
C6 C1 C7 O1 -170.23(14) . . . . ?
C7 C1 C2 C3 -179.32(14) . . . . ?
C7 C1 C6 C5 179.13(14) . . . . ?
C7 C8 O3 C9 -174.84(11) . . . . ?
C9 C10 C11 C12 56.22(16) . . . . ?
C9 C10 C11 C15 -179.55(13) . . . . ?
C10 C9 C14 C13 57.32(17) . . . . ?
C10 C9 O3 C8 -90.99(15) . . . . ?
C10 C11 C12 C13 -55.02(17) . . . . ?
C11 C12 C13 C14 53.91(17) . . . . ?
C11 C12 C13 C16 177.45(13) . . . . ?
C12 C13 C14 C9 -53.59(16) . . . . ?
C14 C9 C10 C11 -58.89(16) . . . . ?
C14 C9 O3 C8 147.06(12) . . . . ?
C15 C11 C12 C13 -178.73(13) . . . . ?
C16 C13 C14 C9 -177.72(13) . . . . ?
O1 C7 C8 O2 -132.93(16) . . . . ?
O1 C7 C8 O3 42.31(18) . . . . ?
O2 C8 O3 C9 0.2(2) . . . . ?
O3 C9 C10 C11 -177.60(11) . . . . ?
O3 C9 C14 C13 177.69(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_deh333
_database_code_depnum_ccdc_archive 'CCDC 2026014'
loop_
_audit_author_name
_audit_author_address
'David Herbert'
;University of Manitoba
Canada
;
_audit_update_record             
;
2020-08-28 deposited with the CCDC.	2020-11-26 downloaded from the CCDC.
;
_audit_creation_date             2020-08-27
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H11 N O2'
_chemical_formula_sum            'C15 H11 N O2'
_chemical_formula_weight         237.25
_chemical_absolute_configuration ?
_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'
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'

_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                   7.0081(3)
_cell_length_b                   12.2782(6)
_cell_length_c                   13.4697(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1159.03(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      27.74
_cell_measurement_theta_min      3.02
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0890 before and 0.0804 after correction.
The Ratio of minimum to maximum transmission is 0.8584.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            pink
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            30662
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.773
_diffrn_reflns_theta_min         3.025
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Quest ECO CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2239
_reflns_number_total             2728
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.237
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 814 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2728
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.040
_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)+(0.0350P)²+0.3099P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0851
_refine_ls_wR_factor_ref         0.0921
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1(0.039) H2(0.04) H3(0.033) H6(0.034) H10(0.032) H11(0.036)
 H13(0.034) H14(0.031) H15A(0.061) H15B(0.061) H15C(0.061)
 Fixed X: H1(0.412716) H2(0.501459) H3(0.515661) H6(0.349643) H10(0.465789)
 H11(0.454984) H13(0.314056) H14(0.331544) H15A(0.503752) H15B(0.297697)
 H15C(0.315851)
 Fixed Y: H1(0.3664) H2(0.185047) H3(0.112667) H6(0.478791) H10(0.35371)
 H11(0.26575) H13(-0.015502) H14(0.069578) H15A(0.04116) H15B(-0.006496)
 H15C(0.108887)
 Fixed Z: H1(-0.010521) H2(0.013695) H3(0.173059) H6(0.125651) H10(0.600829)
 H11(0.753635) H13(0.618017) H14(0.464892) H15A(0.823324) H15B(0.796208)
 H15C(0.850654)
;
_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
O1 O 0.3557(2) 0.42760(11) 0.30871(11) 0.0263(4) Uani 1 1 d . . . . .
O2 O 0.3396(3) 0.45335(13) 0.46963(12) 0.0353(4) Uani 1 1 d . . . . .
N1 N 0.4438(3) 0.20806(15) 0.34098(13) 0.0234(4) Uani 1 1 d . . . . .
C1 C 0.4211(4) 0.3380(2) 0.05493(18) 0.0325(6) Uani 1 1 d . . . . .
H1 H 0.412716 0.366400 -0.010521 0.039 Uiso 1 1 calc R . . . .
C2 C 0.4724(4) 0.2297(2) 0.06927(18) 0.0332(6) Uani 1 1 d . . . . .
H2 H 0.501459 0.185047 0.013695 0.040 Uiso 1 1 calc R . . . .
C3 C 0.4812(3) 0.18681(18) 0.16379(16) 0.0276(5) Uani 1 1 d . . . . .
H3 H 0.515661 0.112667 0.173059 0.033 Uiso 1 1 calc R . . . .
C4 C 0.4399(3) 0.25181(17) 0.24560(15) 0.0230(5) Uani 1 1 d . . . . .
C5 C 0.3922(3) 0.36055(17) 0.22901(16) 0.0234(5) Uani 1 1 d . . . . .
C6 C 0.3824(3) 0.40443(19) 0.13508(16) 0.0280(5) Uani 1 1 d . . . . .
H6 H 0.349643 0.478791 0.125651 0.034 Uiso 1 1 calc R . . . .
C7 C 0.4074(3) 0.27020(18) 0.41583(15) 0.0196(5) Uani 1 1 d . . . . .
C8 C 0.3654(3) 0.38931(18) 0.40451(16) 0.0246(5) Uani 1 1 d . . . . .
C9 C 0.4003(3) 0.22065(18) 0.51626(16) 0.0217(5) Uani 1 1 d . . . . .
C10 C 0.4361(3) 0.2783(2) 0.60373(16) 0.0264(5) Uani 1 1 d . . . . .
H10 H 0.465789 0.353710 0.600829 0.032 Uiso 1 1 calc R . . . .
C11 C 0.4284(3) 0.2257(2) 0.69491(18) 0.0300(5) Uani 1 1 d . . . . .
H11 H 0.454984 0.265750 0.753635 0.036 Uiso 1 1 calc R . . . .
C12 C 0.3829(3) 0.1161(2) 0.70230(17) 0.0287(5) Uani 1 1 d . . . . .
C13 C 0.3462(3) 0.05958(19) 0.61484(17) 0.0282(5) Uani 1 1 d . . . . .
H13 H 0.314056 -0.015502 0.618017 0.034 Uiso 1 1 calc R . . . .
C14 C 0.3557(3) 0.11035(18) 0.52350(17) 0.0256(5) Uani 1 1 d . . . . .
H14 H 0.331544 0.069578 0.464892 0.031 Uiso 1 1 calc R . . . .
C15 C 0.3743(4) 0.0600(2) 0.80184(18) 0.0409(7) Uani 1 1 d . . . . .
H15A H 0.503752 0.041160 0.823324 0.061 Uiso 1 1 calc GR . . . .
H15B H 0.297697 -0.006496 0.796208 0.061 Uiso 1 1 calc GR . . . .
H15C H 0.315851 0.108887 0.850654 0.061 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 C5 1.377(3) . ?
O1 C8 1.375(3) . ?
O2 C8 1.192(3) . ?
N1 C4 1.393(3) . ?
N1 C7 1.290(3) . ?
C1 C2 1.391(4) . ?
C1 C6 1.380(3) . ?
C2 C3 1.379(3) . ?
C3 C4 1.391(3) . ?
C4 C5 1.394(3) . ?
C5 C6 1.377(3) . ?
C7 C8 1.500(3) . ?
C7 C9 1.484(3) . ?
C9 C10 1.397(3) . ?
C9 C14 1.393(3) . ?
C10 C11 1.389(3) . ?
C11 C12 1.387(3) . ?
C12 C13 1.391(3) . ?
C12 C15 1.508(3) . ?
C13 C14 1.381(3) . ?

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 C5 121.20(16) . . ?
C7 N1 C4 119.27(18) . . ?
C6 C1 C2 120.5(2) . . ?
C3 C2 C1 120.3(2) . . ?
C2 C3 C4 120.2(2) . . ?
N1 C4 C5 121.46(19) . . ?
C3 C4 N1 120.35(19) . . ?
C3 C4 C5 118.18(19) . . ?
O1 C5 C4 119.48(19) . . ?
C6 C5 O1 118.24(19) . . ?
C6 C5 C4 122.3(2) . . ?
C5 C6 C1 118.5(2) . . ?
N1 C7 C8 122.43(19) . . ?
N1 C7 C9 118.47(19) . . ?
C9 C7 C8 119.07(19) . . ?
O1 C8 C7 116.01(18) . . ?
O2 C8 O1 117.23(19) . . ?
O2 C8 C7 126.8(2) . . ?
C10 C9 C7 123.7(2) . . ?
C14 C9 C7 118.0(2) . . ?
C14 C9 C10 118.3(2) . . ?
C11 C10 C9 120.2(2) . . ?
C12 C11 C10 121.6(2) . . ?
C11 C12 C13 117.8(2) . . ?
C11 C12 C15 121.1(2) . . ?
C13 C12 C15 121.2(2) . . ?
C14 C13 C12 121.4(2) . . ?
C13 C14 C9 120.8(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_deh229
_database_code_depnum_ccdc_archive 'CCDC 2024462'
loop_
_audit_author_name
_audit_author_address
'David Herbert'
;University of Manitoba
Canada
;
_audit_update_record             
;
2020-08-20 deposited with the CCDC.	2020-11-26 downloaded from the CCDC.
;
_audit_creation_date             2019-02-01
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
# end Validation Reply Form
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 F3 N O2'
_chemical_formula_sum            'C15 H10 F3 N O2'
_chemical_formula_weight         293.24
_chemical_absolute_configuration ?
_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'
F F 0.0171 0.0103 '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'

_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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   24.5598(16)
_cell_length_b                   4.6673(3)
_cell_length_c                   11.1063(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.835(2)
_cell_angle_gamma                90
_cell_volume                     1271.53(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7524
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      3.32
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6296
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0712 before and 0.0612 after correction.
The Ratio of minimum to maximum transmission is 0.8444.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18036
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.517
_diffrn_reflns_theta_min         3.322
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 QUEST ECO CMOS'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'TRIUMPH curved--crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.991
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                2463
_reflns_number_total             2901
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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-97 (Sheldrick 2008)'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 1064 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2901
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      1.063
_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)+(0.0291P)²+0.8474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0830
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C7(H7)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C6(H6), C10(H10), C11(H11), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C -0.09507(13) 0.9048(8) 0.7044(3) 0.0377(8) Uani 1 1 d . . . . .
H1 H -0.128989 0.967945 0.669047 0.045 Uiso 1 1 calc R . . . .
C2 C -0.07634(14) 1.0117(8) 0.8155(3) 0.0393(8) Uani 1 1 d . . . . .
H2 H -0.097740 1.147209 0.856035 0.047 Uiso 1 1 calc R . . . .
C3 C -0.02689(13) 0.9233(7) 0.8678(3) 0.0327(7) Uani 1 1 d . . . . .
H3 H -0.014460 0.998099 0.943856 0.039 Uiso 1 1 calc R . . . .
C4 C 0.00456(11) 0.7249(6) 0.8090(3) 0.0237(6) Uani 1 1 d . . . . .
C5 C -0.01534(12) 0.6220(7) 0.6986(3) 0.0254(6) Uani 1 1 d . . . . .
C6 C -0.06423(13) 0.7060(7) 0.6451(3) 0.0324(7) Uani 1 1 d . . . . .
H6 H -0.076643 0.629713 0.569373 0.039 Uiso 1 1 calc R . . . .
C7 C 0.09346(11) 0.5472(6) 0.7676(2) 0.0212(6) Uani 1 1 d . . . . .
H7 H 0.104975 0.730470 0.729736 0.025 Uiso 1 1 calc R . . . .
C8 C 0.06637(12) 0.3611(6) 0.6701(2) 0.0233(6) Uani 1 1 d . . . . .
C9 C 0.14354(12) 0.4033(6) 0.8242(2) 0.0223(6) Uani 1 1 d . . . . .
C10 C 0.14004(13) 0.2323(6) 0.9261(3) 0.0239(6) Uani 1 1 d . . . . .
H10 H 0.105788 0.205198 0.960642 0.029 Uiso 1 1 calc R . . . .
C11 C 0.18602(12) 0.1016(6) 0.9775(3) 0.0267(6) Uani 1 1 d . . . . .
H11 H 0.183361 -0.016866 1.046503 0.032 Uiso 1 1 calc R . . . .
C12 C 0.23584(12) 0.1440(7) 0.9280(3) 0.0290(7) Uani 1 1 d . . . . .
C13 C 0.23978(13) 0.3097(7) 0.8259(3) 0.0314(7) Uani 1 1 d . . . . .
H13 H 0.274079 0.334962 0.791367 0.038 Uiso 1 1 calc R . . . .
C14 C 0.19375(12) 0.4388(7) 0.7740(3) 0.0291(7) Uani 1 1 d . . . . .
H14 H 0.196473 0.552487 0.703596 0.035 Uiso 1 1 calc R . . . .
C16 C 0.28568(14) 0.0171(8) 0.9895(4) 0.0452(9) Uani 1 1 d . . . . .
F1 F 0.2944(3) 0.1457(17) 1.1031(5) 0.0514(18) Uani 0.60(3) 1 d . . P A 1
F2 F 0.3308(3) 0.068(5) 0.9407(9) 0.088(5) Uani 0.60(3) 1 d . . P A 1
F3 F 0.2819(5) -0.2490(18) 1.0192(14) 0.090(4) Uani 0.60(3) 1 d . . P A 1
F1A F 0.3154(12) 0.171(3) 1.045(4) 0.146(14) Uani 0.40(3) 1 d . . P A 2
F2A F 0.3170(6) -0.103(4) 0.8959(17) 0.081(5) Uani 0.40(3) 1 d . . P A 2
F3A F 0.2752(5) -0.231(3) 1.0416(11) 0.052(3) Uani 0.40(3) 1 d . . P A 2
N2 N 0.05391(10) 0.6144(6) 0.8569(2) 0.0243(5) Uani 1 1 d . . . . .
O1 O 0.01390(8) 0.4105(4) 0.63903(17) 0.0280(5) Uani 1 1 d . . . . .
O2 O 0.08981(9) 0.1780(5) 0.61601(18) 0.0313(5) Uani 1 1 d . . . . .
H2A H 0.0676(15) 0.698(8) 0.924(3) 0.035(10) Uiso 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 C2 1.388(5) . ?
C1 C6 1.385(5) . ?
C2 C3 1.383(5) . ?
C3 C4 1.390(4) . ?
C4 C5 1.383(4) . ?
C4 N2 1.398(4) . ?
C5 C6 1.370(4) . ?
C5 O1 1.405(4) . ?
C7 C8 1.515(4) . ?
C7 C9 1.511(4) . ?
C7 N2 1.457(4) . ?
C8 O1 1.338(3) . ?
C8 O2 1.207(3) . ?
C9 C10 1.391(4) . ?
C9 C14 1.388(4) . ?
C10 C11 1.382(4) . ?
C11 C12 1.380(4) . ?
C12 C13 1.380(4) . ?
C12 C16 1.494(4) . ?
C13 C14 1.382(4) . ?
C16 F1 1.405(7) . ?
C16 F2 1.280(8) . ?
C16 F3 1.289(10) . ?
C16 F1A 1.178(11) . ?
C16 F2A 1.437(16) . ?
C16 F3A 1.324(12) . ?

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 119.9(3) . . ?
C3 C2 C1 120.8(3) . . ?
C2 C3 C4 119.9(3) . . ?
C3 C4 N2 124.0(3) . . ?
C5 C4 C3 117.9(3) . . ?
C5 C4 N2 118.1(3) . . ?
C4 C5 O1 119.7(2) . . ?
C6 C5 C4 123.2(3) . . ?
C6 C5 O1 117.0(3) . . ?
C5 C6 C1 118.3(3) . . ?
C9 C7 C8 111.2(2) . . ?
N2 C7 C8 109.0(2) . . ?
N2 C7 C9 111.6(2) . . ?
O1 C8 C7 118.0(2) . . ?
O2 C8 C7 123.9(3) . . ?
O2 C8 O1 118.1(3) . . ?
C10 C9 C7 120.8(3) . . ?
C14 C9 C7 120.0(3) . . ?
C14 C9 C10 119.2(3) . . ?
C11 C10 C9 120.5(3) . . ?
C12 C11 C10 119.7(3) . . ?
C11 C12 C16 118.9(3) . . ?
C13 C12 C11 120.5(3) . . ?
C13 C12 C16 120.6(3) . . ?
C12 C13 C14 119.9(3) . . ?
C13 C14 C9 120.3(3) . . ?
F1 C16 C12 109.1(4) . . ?
F2 C16 C12 116.0(4) . . ?
F2 C16 F1 101.7(8) . . ?
F2 C16 F3 111.4(8) . . ?
F3 C16 C12 115.5(6) . . ?
F3 C16 F1 101.0(7) . . ?
F1A C16 C12 118.0(6) . . ?
F1A C16 F2A 106.1(16) . . ?
F1A C16 F3A 115.7(18) . . ?
F2A C16 C12 106.2(7) . . ?
F3A C16 C12 112.0(7) . . ?
F3A C16 F2A 95.6(8) . . ?
C4 N2 C7 114.5(2) . . ?
C8 O1 C5 120.5(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT213_deh229              
;
PROBLEM: Atom F1A             has ADP max/min Ratio .....        4.2 prolat
RESPONSE: Due to unresolved disorder in a freely rotating CF3 group.
;
####################################################################### 
# 
# 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_deh332_tw
_database_code_depnum_ccdc_archive 'CCDC 2026013'
loop_
_audit_author_name
_audit_author_address
'David Herbert'
;University of Manitoba
Canada
;
_audit_update_record             
;
2020-08-28 deposited with the CCDC.	2020-11-26 downloaded from the CCDC.
;
_audit_creation_date             2020-08-27
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H8 Cl N O2'
_chemical_formula_sum            'C14 H8 Cl N O2'
_chemical_formula_weight         257.66
_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'
Cl Cl 0.1484 0.1585 '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'

_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                   3.8058(2)
_cell_length_b                   21.9865(13)
_cell_length_c                   13.2467(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.488(2)
_cell_angle_gamma                90
_cell_volume                     1105.04(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      3.09
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.816
_exptl_absorpt_coefficient_mu    0.336
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1095 before and 0.0823 after correction.
The Ratio of minimum to maximum transmission is 0.8876.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1095
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            2522
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.575
_diffrn_reflns_theta_min         3.085
_diffrn_ambient_temperature      150.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Quest ECO CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2113
_reflns_number_total             2522
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.372
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.299
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2522
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0695
_refine_ls_restrained_S_all      1.299
_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)+3.4464P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1497
_refine_ls_wR_factor_ref         0.1556
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1(0.025) H2(0.026) H3(0.022) H6(0.023) H10(0.022) H11(0.026)
 H13(0.025) H14(0.022)
 Fixed X: H1(-0.002295) H2(-0.161334) H3(-0.074364) H6(0.248724) H10(0.241502)
 H11(0.329245) H13(0.693576) H14(0.574299)
 Fixed Y: H1(0.353713) H2(0.448811) H3(0.471297) H6(0.280611) H10(0.291962)
 H11(0.314449) H13(0.481732) H14(0.460486)
 Fixed Z: H1(0.823518) H2(0.755504) H3(0.587539) H6(0.72461) H10(0.235558)
 H11(0.06703) H13(0.152462) H14(0.319501)
;
_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
Cl1 Cl 0.6126(3) 0.41505(5) -0.02775(7) 0.0310(3) Uani 1 1 d . . . . .
O1 O 0.3931(8) 0.28942(11) 0.54077(19) 0.0189(6) Uani 1 1 d . . . . .
O2 O 0.6338(9) 0.26479(13) 0.4009(2) 0.0282(7) Uani 1 1 d . . . . .
N1 N 0.1960(8) 0.40237(14) 0.4540(2) 0.0166(7) Uani 1 1 d . . . . .
C1 C 0.0358(11) 0.36248(18) 0.7550(3) 0.0212(8) Uani 1 1 d . . . . .
H1 H -0.002295 0.353713 0.823518 0.025 Uiso 1 1 calc R . . . .
C2 C -0.0598(11) 0.41923(18) 0.7144(3) 0.0213(8) Uani 1 1 d . . . . .
H2 H -0.161334 0.448811 0.755504 0.026 Uiso 1 1 calc R . . . .
C3 C -0.0078(10) 0.43268(17) 0.6149(3) 0.0181(8) Uani 1 1 d . . . . .
H3 H -0.074364 0.471297 0.587539 0.022 Uiso 1 1 calc R . . . .
C4 C 0.1436(10) 0.38913(16) 0.5546(3) 0.0150(7) Uani 1 1 d . . . . .
C5 C 0.2373(10) 0.33299(17) 0.5975(3) 0.0155(7) Uani 1 1 d . . . . .
C6 C 0.1840(11) 0.31926(17) 0.6970(3) 0.0193(8) Uani 1 1 d . . . . .
H6 H 0.248724 0.280611 0.724610 0.023 Uiso 1 1 calc R . . . .
C7 C 0.3398(10) 0.36129(17) 0.4009(3) 0.0163(8) Uani 1 1 d . . . . .
C8 C 0.4638(11) 0.30148(17) 0.4438(3) 0.0194(8) Uani 1 1 d . . . . .
C9 C 0.4016(10) 0.37377(17) 0.2943(3) 0.0163(8) Uani 1 1 d . . . . .
C10 C 0.3299(10) 0.33074(18) 0.2186(3) 0.0185(8) Uani 1 1 d . . . . .
H10 H 0.241502 0.291962 0.235558 0.022 Uiso 1 1 calc R . . . .
C11 C 0.3852(11) 0.34355(18) 0.1188(3) 0.0219(8) Uani 1 1 d . . . . .
H11 H 0.329245 0.314449 0.067030 0.026 Uiso 1 1 calc R . . . .
C12 C 0.5233(11) 0.39940(18) 0.0961(3) 0.0198(8) Uani 1 1 d . . . . .
C13 C 0.5984(11) 0.44349(18) 0.1696(3) 0.0208(8) Uani 1 1 d . . . . .
H13 H 0.693576 0.481732 0.152462 0.025 Uiso 1 1 calc R . . . .
C14 C 0.5313(10) 0.43040(17) 0.2686(3) 0.0187(8) Uani 1 1 d . . . . .
H14 H 0.574299 0.460486 0.319501 0.022 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
Cl1 C12 1.736(4) . ?
O1 C5 1.380(4) . ?
O1 C8 1.359(4) . ?
O2 C8 1.204(5) . ?
N1 C4 1.393(4) . ?
N1 C7 1.293(5) . ?
C1 C2 1.396(6) . ?
C1 C6 1.371(5) . ?
C2 C3 1.379(5) . ?
C3 C4 1.400(5) . ?
C4 C5 1.394(5) . ?
C5 C6 1.382(5) . ?
C7 C8 1.494(5) . ?
C7 C9 1.475(5) . ?
C9 C10 1.391(5) . ?
C9 C14 1.392(5) . ?
C10 C11 1.383(5) . ?
C11 C12 1.378(6) . ?
C12 C13 1.388(5) . ?
C13 C14 1.385(5) . ?

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 C5 120.3(3) . . ?
C7 N1 C4 118.2(3) . . ?
C6 C1 C2 120.6(3) . . ?
C3 C2 C1 120.5(4) . . ?
C2 C3 C4 119.7(4) . . ?
N1 C4 C3 119.9(3) . . ?
N1 C4 C5 121.6(3) . . ?
C5 C4 C3 118.4(3) . . ?
O1 C5 C4 120.0(3) . . ?
O1 C5 C6 118.0(3) . . ?
C6 C5 C4 122.0(3) . . ?
C1 C6 C5 118.7(4) . . ?
N1 C7 C8 122.9(3) . . ?
N1 C7 C9 119.8(3) . . ?
C9 C7 C8 117.3(3) . . ?
O1 C8 C7 116.8(3) . . ?
O2 C8 O1 118.0(3) . . ?
O2 C8 C7 125.1(3) . . ?
C10 C9 C7 121.8(3) . . ?
C10 C9 C14 119.0(3) . . ?
C14 C9 C7 119.2(3) . . ?
C11 C10 C9 121.0(4) . . ?
C12 C11 C10 118.6(4) . . ?
C11 C12 Cl1 119.3(3) . . ?
C11 C12 C13 122.1(3) . . ?
C13 C12 Cl1 118.7(3) . . ?
C14 C13 C12 118.4(4) . . ?
C13 C14 C9 120.9(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.788(4)
2 0.212(4)

