# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_mo230428a
_database_code_depnum_ccdc_archive 'CCDC 2265957'
loop_
_audit_author_name
_audit_author_address
'Pinglu Zhang'
;Hangzhou Normal University
China
;
_audit_update_record             
;
2023-05-29 deposited with the CCDC.	2023-11-08 downloaded from the CCDC.
;
_audit_creation_date             2023-05-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6427)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H17 N O'
_chemical_formula_sum            'C17 H17 N O'
_chemical_formula_weight         251.31
_chemical_absolute_configuration unk
_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                   6.9302(9)
_cell_length_b                   10.5748(14)
_cell_length_c                   19.067(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1397.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4827
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      22.538
_cell_measurement_theta_min      2.202
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0573 before and 0.0523 after correction.
The Ratio of minimum to maximum transmission is 0.9400.
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    1.195
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.15
_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  0.0436
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            20151
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.500
_diffrn_reflns_theta_min         2.136
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.913
_reflns_number_gt                3039
_reflns_number_total             3983
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Flack x determined using 1047 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3983
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.024
_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)+(0.0510P)²+0.1287P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1102
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C15(H15),
 C16(H16)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_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 0.5046(2) 0.92140(13) 0.33710(8) 0.0544(4) Uani 1 1 d . . . . .
N1 N 0.6534(3) 0.17015(16) 0.38610(11) 0.0583(5) Uani 1 1 d . . . . .
H1 H 0.588656 0.101973 0.378978 0.070 Uiso 1 1 calc R U . . .
C2 C 0.6138(3) 0.25948(18) 0.43675(13) 0.0528(5) Uani 1 1 d . . . . .
H2 H 0.512813 0.254818 0.468772 0.063 Uiso 1 1 calc R U . . .
C3 C 0.7438(3) 0.35522(16) 0.43300(9) 0.0396(4) Uani 1 1 d . . . . .
C4 C 0.8730(3) 0.32422(17) 0.37699(10) 0.0406(4) Uani 1 1 d . . . . .
C5 C 1.0358(3) 0.3822(2) 0.34829(13) 0.0564(6) Uani 1 1 d . . . . .
H5 H 1.080351 0.458839 0.365937 0.068 Uiso 1 1 calc R U . . .
C6 C 1.1296(4) 0.3237(3) 0.29321(15) 0.0756(8) Uani 1 1 d . . . . .
H6 H 1.238221 0.361786 0.273801 0.091 Uiso 1 1 calc R U . . .
C7 C 1.0650(5) 0.2090(3) 0.26612(14) 0.0781(9) Uani 1 1 d . . . . .
H7 H 1.130119 0.172634 0.228542 0.094 Uiso 1 1 calc R U . . .
C8 C 0.9083(4) 0.1489(2) 0.29360(12) 0.0644(7) Uani 1 1 d . . . . .
H8 H 0.866800 0.071575 0.275971 0.077 Uiso 1 1 calc R U . . .
C9 C 0.8123(3) 0.20749(19) 0.34904(11) 0.0474(5) Uani 1 1 d . . . . .
C10 C 0.7526(3) 0.47337(17) 0.47702(10) 0.0428(4) Uani 1 1 d . . . . .
H10 H 0.887994 0.486566 0.489993 0.051 Uiso 1 1 calc R U . . .
C11 C 0.6865(3) 0.59078(17) 0.43701(9) 0.0396(4) Uani 1 1 d . . . . .
C12 C 0.7780(3) 0.7057(2) 0.44603(11) 0.0503(5) Uani 1 1 d . . . . .
H12 H 0.885102 0.710564 0.475311 0.060 Uiso 1 1 calc R U . . .
C13 C 0.7139(3) 0.81353(19) 0.41250(12) 0.0524(5) Uani 1 1 d . . . . .
H13 H 0.777697 0.889865 0.419503 0.063 Uiso 1 1 calc R U . . .
C14 C 0.5559(3) 0.80866(17) 0.36873(10) 0.0415(4) Uani 1 1 d . . . . .
C15 C 0.4604(3) 0.69576(19) 0.35909(12) 0.0503(5) Uani 1 1 d . . . . .
H15 H 0.352711 0.691470 0.330073 0.060 Uiso 1 1 calc R U . . .
C16 C 0.5272(3) 0.58844(19) 0.39332(12) 0.0503(5) Uani 1 1 d . . . . .
H16 H 0.462558 0.512316 0.386637 0.060 Uiso 1 1 calc R U . . .
C17 C 0.6377(4) 0.4605(2) 0.54501(11) 0.0636(6) Uani 1 1 d . . . . .
H17A H 0.505009 0.443301 0.534153 0.095 Uiso 1 1 calc R U . . .
H17B H 0.646277 0.537875 0.571198 0.095 Uiso 1 1 calc R U . . .
H17C H 0.689540 0.392382 0.572414 0.095 Uiso 1 1 calc R U . . .
C18 C 0.3597(4) 0.9171(2) 0.28433(14) 0.0675(7) Uani 1 1 d . . . . .
H18A H 0.398853 0.860081 0.247832 0.101 Uiso 1 1 calc R U . . .
H18B H 0.341702 1.000120 0.265046 0.101 Uiso 1 1 calc R U . . .
H18C H 0.240666 0.888175 0.304501 0.101 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
O1 C14 1.383(2) . ?
O1 C18 1.422(3) . ?
N1 H1 0.8600 . ?
N1 C2 1.379(3) . ?
N1 C9 1.367(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.357(3) . ?
C3 C4 1.432(3) . ?
C3 C10 1.506(3) . ?
C4 C5 1.396(3) . ?
C4 C9 1.409(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.381(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.393(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.363(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.394(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.528(3) . ?
C10 C17 1.528(3) . ?
C11 C12 1.382(3) . ?
C11 C16 1.383(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.378(3) . ?
C14 C15 1.377(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.389(3) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

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
C14 O1 C18 117.55(16) . . ?
C2 N1 H1 125.5 . . ?
C9 N1 H1 125.5 . . ?
C9 N1 C2 108.95(18) . . ?
N1 C2 H2 125.0 . . ?
C3 C2 N1 110.0(2) . . ?
C3 C2 H2 125.0 . . ?
C2 C3 C4 106.48(17) . . ?
C2 C3 C10 128.06(19) . . ?
C4 C3 C10 125.45(17) . . ?
C5 C4 C3 134.22(19) . . ?
C5 C4 C9 118.6(2) . . ?
C9 C4 C3 107.21(18) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.8(2) . . ?
C6 C5 H5 120.6 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.4(3) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.3(2) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 121.2 . . ?
C7 C8 C9 117.7(2) . . ?
C9 C8 H8 121.2 . . ?
N1 C9 C4 107.36(18) . . ?
N1 C9 C8 130.4(2) . . ?
C8 C9 C4 122.2(2) . . ?
C3 C10 H10 107.3 . . ?
C3 C10 C11 112.56(15) . . ?
C3 C10 C17 112.20(17) . . ?
C11 C10 H10 107.3 . . ?
C17 C10 H10 107.3 . . ?
C17 C10 C11 109.84(17) . . ?
C12 C11 C10 120.99(17) . . ?
C12 C11 C16 117.20(17) . . ?
C16 C11 C10 121.72(17) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.39(18) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.37(18) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 O1 115.87(17) . . ?
C15 C14 O1 124.45(17) . . ?
C15 C14 C13 119.68(18) . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C16 119.04(18) . . ?
C16 C15 H15 120.5 . . ?
C11 C16 C15 122.31(18) . . ?
C11 C16 H16 118.8 . . ?
C15 C16 H16 118.8 . . ?
C10 C17 H17A 109.5 . . ?
C10 C17 H17B 109.5 . . ?
C10 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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 C14 C15 C16 179.4(2) . . . . ?
N1 C2 C3 C4 -0.2(2) . . . . ?
N1 C2 C3 C10 178.60(19) . . . . ?
C2 N1 C9 C4 -0.5(2) . . . . ?
C2 N1 C9 C8 179.3(2) . . . . ?
C2 C3 C4 C5 -178.8(2) . . . . ?
C2 C3 C4 C9 -0.1(2) . . . . ?
C2 C3 C10 C11 -105.7(2) . . . . ?
C2 C3 C10 C17 18.8(3) . . . . ?
C3 C4 C5 C6 179.4(2) . . . . ?
C3 C4 C9 N1 0.3(2) . . . . ?
C3 C4 C9 C8 -179.49(19) . . . . ?
C3 C10 C11 C12 -141.6(2) . . . . ?
C3 C10 C11 C16 41.9(3) . . . . ?
C4 C3 C10 C11 72.9(2) . . . . ?
C4 C3 C10 C17 -162.59(19) . . . . ?
C4 C5 C6 C7 0.0(4) . . . . ?
C5 C4 C9 N1 179.32(18) . . . . ?
C5 C4 C9 C8 -0.5(3) . . . . ?
C5 C6 C7 C8 -1.0(4) . . . . ?
C6 C7 C8 C9 1.2(4) . . . . ?
C7 C8 C9 N1 179.8(2) . . . . ?
C7 C8 C9 C4 -0.4(3) . . . . ?
C9 N1 C2 C3 0.4(2) . . . . ?
C9 C4 C5 C6 0.7(3) . . . . ?
C10 C3 C4 C5 2.3(3) . . . . ?
C10 C3 C4 C9 -178.93(17) . . . . ?
C10 C11 C12 C13 -177.1(2) . . . . ?
C10 C11 C16 C15 177.1(2) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C11 C16 C15 0.4(3) . . . . ?
C12 C13 C14 O1 -179.3(2) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C13 C14 C15 C16 -0.7(3) . . . . ?
C14 C15 C16 C11 0.1(4) . . . . ?
C16 C11 C12 C13 -0.4(3) . . . . ?
C17 C10 C11 C12 92.6(2) . . . . ?
C17 C10 C11 C16 -83.9(2) . . . . ?
C18 O1 C14 C13 171.5(2) . . . . ?
C18 O1 C14 C15 -8.5(3) . . . . ?

_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_mo230505b
_database_code_depnum_ccdc_archive 'CCDC 2265959'
loop_
_audit_author_name
_audit_author_address
'Pinglu Zhang'
;Hangzhou Normal University
China
;
_audit_update_record             
;
2023-05-29 deposited with the CCDC.	2023-11-08 downloaded from the CCDC.
;
_audit_creation_date             2023-05-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6427)
;
_chemical_formula_moiety         'C17 H15 F2 N O'
_chemical_formula_sum            'C17 H15 F2 N O'
_chemical_formula_weight         287.311
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   7.4260(14)
_cell_length_b                   10.475(2)
_cell_length_c                   18.684(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1453.4(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1324
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      20.277
_cell_measurement_theta_min      2.229
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0981 before and 0.0732 after correction.
The Ratio of minimum to maximum transmission is 0.8183.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             600.363
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_unetI/netI     0.1065
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9356
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10744
_diffrn_reflns_point_group_measured_fraction_full 1.0000
_diffrn_reflns_point_group_measured_fraction_max 0.9058
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         30.48
_diffrn_reflns_theta_min         2.18
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9356
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.866
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              25
_reflns_limit_l_min              -25
_reflns_number_gt                1887
_reflns_number_total             4011
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.3046
_refine_diff_density_min         -0.3389
_refine_diff_density_rms         0.0756
_refine_ls_abs_structure_details 
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.3(11)
_refine_ls_d_res_high            0.7007
_refine_ls_d_res_low             9.3420
_refine_ls_goodness_of_fit_ref   1.0461
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     192
_refine_ls_number_reflns         4011
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1470
_refine_ls_R_factor_gt           0.0542
_refine_ls_restrained_S_all      1.0461
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0392P)²+0.0077P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1554
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C11(H11), C12(H12), C15(H15), C14(H14), C1(H1a), C7(H7), C6(H6)
2.c Idealised Me refined as rotating group:
 C17(H17a,H17b,H17c), C16(H16a,H16b,H16c)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
F1 F 0.4263(2) 0.50833(18) 0.38355(11) 0.0808(6) Uani 1.000000 .
O1 O 1.0150(3) 0.06674(16) 0.34321(10) 0.0577(6) Uani 1.000000 .
F2 F 0.2417(3) 0.6220(2) 0.27927(14) 0.1150(9) Uani 1.000000 .
N1 N 0.8583(4) 0.8234(2) 0.38352(18) 0.0765(8) Uani 1.000000 .
H1 H 0.9201(4) 0.8907(2) 0.37409(18) 0.0918(10) Uiso 1.000000 R
C13 C 0.9602(4) 0.1813(2) 0.37301(14) 0.0460(7) Uani 1.000000 .
C3 C 0.6494(4) 0.6713(2) 0.38093(15) 0.0477(7) Uani 1.000000 .
C2 C 0.7756(4) 0.6394(2) 0.43579(15) 0.0497(7) Uani 1.000000 .
C10 C 0.8350(4) 0.4026(2) 0.44016(14) 0.0451(7) Uani 1.000000 .
C11 C 0.9787(4) 0.4050(2) 0.39364(16) 0.0545(8) Uani 1.000000 .
H11 H 1.0354(4) 0.4825(2) 0.38455(16) 0.0654(9) Uiso 1.000000 R
C12 C 1.0421(4) 0.2959(3) 0.35982(16) 0.0555(8) Uani 1.000000 .
H12 H 1.1392(4) 0.3007(3) 0.32850(16) 0.0666(10) Uiso 1.000000 R
C9 C 0.7740(5) 0.5209(3) 0.48120(14) 0.0529(7) Uani 1.000000 .
H9 H 0.6495(5) 0.5063(3) 0.49651(14) 0.0635(9) Uiso 1.000000 R
C15 C 0.7552(4) 0.2856(3) 0.45202(17) 0.0593(8) Uani 1.000000 .
H15 H 0.6576(4) 0.2802(3) 0.48304(17) 0.0711(10) Uiso 1.000000 R
C8 C 0.7038(5) 0.7875(3) 0.34941(18) 0.0607(9) Uani 1.000000 .
C4 C 0.4892(5) 0.6182(3) 0.35516(16) 0.0571(8) Uani 1.000000 .
C14 C 0.8170(4) 0.1762(3) 0.41886(17) 0.0610(8) Uani 1.000000 .
H14 H 0.7608(4) 0.0985(3) 0.42781(17) 0.0732(10) Uiso 1.000000 R
C1 C 0.8992(5) 0.7352(3) 0.4351(2) 0.0676(9) Uani 1.000000 .
H1a H 0.9980(5) 0.7402(3) 0.4655(2) 0.0812(11) Uiso 1.000000 R
C5 C 0.3985(5) 0.6764(4) 0.3021(2) 0.0731(10) Uani 1.000000 .
C7 C 0.6105(6) 0.8457(3) 0.2943(2) 0.0803(11) Uani 1.000000 .
H7 H 0.6510(6) 0.9218(3) 0.2743(2) 0.0964(14) Uiso 1.000000 R
C17 C 1.1410(5) 0.0705(3) 0.28599(18) 0.0726(10) Uani 1.000000 .
H17a H 1.0988(16) 0.1282(18) 0.2497(6) 0.1089(15) Uiso 1.000000 GR
H17b H 1.2554(9) 0.099(2) 0.3036(3) 0.1089(15) Uiso 1.000000 GR
H17c H 1.154(2) -0.0134(6) 0.2659(9) 0.1089(15) Uiso 1.000000 GR
C16 C 0.8877(5) 0.5361(3) 0.54821(17) 0.0790(11) Uani 1.000000 .
H16a H 1.0110(8) 0.550(2) 0.53493(17) 0.1185(16) Uiso 1.000000 GR
H16b H 0.845(2) 0.6077(15) 0.5754(7) 0.1185(16) Uiso 1.000000 GR
H16c H 0.879(3) 0.4600(10) 0.5767(7) 0.1185(16) Uiso 1.000000 GR
C6 C 0.4574(7) 0.7882(4) 0.2700(2) 0.0892(14) Uani 1.000000 .
H6 H 0.3930(7) 0.8237(4) 0.2322(2) 0.1070(16) Uiso 1.000000 R


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
F1 C4 1.351(3) . ?
O1 C13 1.384(3) . ?
O1 C17 1.421(3) . ?
F2 C5 1.365(4) . ?
N1 H1 0.8600 . ?
N1 C8 1.365(4) . ?
N1 C1 1.369(4) . ?
C13 C12 1.368(3) . ?
C13 C14 1.367(4) . ?
C3 C2 1.429(4) . ?
C3 C8 1.411(4) . ?
C3 C4 1.398(4) . ?
C2 C9 1.504(4) . ?
C2 C1 1.360(4) . ?
C10 C11 1.377(4) . ?
C10 C9 1.526(4) . ?
C10 C15 1.379(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.388(4) . ?
C12 H12 0.9300 . ?
C9 H9 0.9800 . ?
C9 C16 1.518(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.381(4) . ?
C8 C7 1.383(5) . ?
C4 C5 1.345(4) . ?
C14 H14 0.9300 . ?
C1 H1a 0.9300 . ?
C5 C6 1.386(5) . ?
C7 H7 0.9300 . ?
C7 C6 1.365(5) . ?
C17 H17a 0.9600 . ?
C17 H17b 0.9600 . ?
C17 H17c 0.9600 . ?
C16 H16a 0.9600 . ?
C16 H16b 0.9600 . ?
C16 H16c 0.9600 . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 O1 C13 118.2(2) . . ?
C8 N1 H1 125.39(18) . . ?
C1 N1 H1 125.4(2) . . ?
C1 N1 C8 109.2(3) . . ?
C12 C13 O1 123.9(2) . . ?
C14 C13 O1 116.6(2) . . ?
C14 C13 C12 119.5(2) . . ?
C8 C3 C2 108.3(3) . . ?
C4 C3 C2 135.4(3) . . ?
C4 C3 C8 116.3(3) . . ?
C9 C2 C3 126.4(2) . . ?
C1 C2 C3 105.2(3) . . ?
C1 C2 C9 128.3(3) . . ?
C9 C10 C11 122.2(2) . . ?
C15 C10 C11 116.8(2) . . ?
C15 C10 C9 120.9(2) . . ?
H11 C11 C10 118.82(15) . . ?
C12 C11 C10 122.4(2) . . ?
C12 C11 H11 118.82(16) . . ?
C11 C12 C13 119.3(3) . . ?
H12 C12 C13 120.33(16) . . ?
H12 C12 C11 120.33(16) . . ?
C10 C9 C2 112.6(2) . . ?
H9 C9 C2 107.48(17) . . ?
H9 C9 C10 107.48(17) . . ?
C16 C9 C2 112.0(3) . . ?
C16 C9 C10 109.5(2) . . ?
C16 C9 H9 107.48(19) . . ?
H15 C15 C10 119.25(16) . . ?
C14 C15 C10 121.5(3) . . ?
C14 C15 H15 119.25(17) . . ?
C3 C8 N1 106.5(3) . . ?
C7 C8 N1 130.3(3) . . ?
C7 C8 C3 123.2(4) . . ?
C3 C4 F1 119.9(3) . . ?
C5 C4 F1 120.1(3) . . ?
C5 C4 C3 120.0(3) . . ?
C15 C14 C13 120.5(3) . . ?
H14 C14 C13 119.76(16) . . ?
H14 C14 C15 119.76(17) . . ?
C2 C1 N1 110.8(3) . . ?
H1a C1 N1 124.6(2) . . ?
H1a C1 C2 124.6(2) . . ?
C4 C5 F2 118.0(4) . . ?
C6 C5 F2 119.1(4) . . ?
C6 C5 C4 122.9(4) . . ?
H7 C7 C8 121.0(2) . . ?
C6 C7 C8 118.1(4) . . ?
C6 C7 H7 121.0(2) . . ?
H17a C17 O1 109.5 . . ?
H17b C17 O1 109.5 . . ?
H17b C17 H17a 109.5 . . ?
H17c C17 O1 109.5 . . ?
H17c C17 H17a 109.5 . . ?
H17c C17 H17b 109.5 . . ?
H16a C16 C9 109.5 . . ?
H16b C16 C9 109.5 . . ?
H16b C16 H16a 109.5 . . ?
H16c C16 C9 109.5 . . ?
H16c C16 H16a 109.5 . . ?
H16c C16 H16b 109.5 . . ?
C7 C6 C5 119.5(4) . . ?
H6 C6 C5 120.3(3) . . ?
H6 C6 C7 120.3(2) . . ?

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
F1 C4 C3 C2 -1.9(4) . . . . ?
F1 C4 C3 C8 -178.7(3) . . . . ?
F1 C4 C5 F2 1.0(3) . . . . ?
F1 C4 C5 C6 -179.0(3) . . . . ?
O1 C13 C12 C11 -178.7(3) . . . . ?
O1 C13 C14 C15 178.9(3) . . . . ?
F2 C5 C4 C3 -179.2(3) . . . . ?
F2 C5 C6 C7 177.6(3) . . . . ?
N1 C8 C3 C2 0.7(3) . . . . ?
N1 C8 C3 C4 178.3(2) . . . . ?
N1 C8 C7 C6 -180.0(4) . . . . ?
N1 C1 C2 C3 -0.3(3) . . . . ?
N1 C1 C2 C9 176.8(2) . . . . ?
C13 C12 C11 C10 -0.3(3) . . . . ?
C13 C14 C15 C10 -0.0(4) . . . . ?
C3 C2 C9 C10 74.1(3) . . . . ?
C3 C2 C9 C16 -161.9(3) . . . . ?
C3 C8 C7 C6 0.8(3) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C2 C9 C10 C11 41.8(3) . . . . ?
C2 C9 C10 C15 -142.7(3) . . . . ?
C8 C7 C6 C5 1.5(4) . . . . ?
C4 C5 C6 C7 -2.4(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
