# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_IIa
_audit_block_doi                 10.5517/ccdc.csd.cc2dzspw
_database_code_depnum_ccdc_archive 'CCDC 2234129'
loop_
_audit_author_name
_audit_author_address
'Steven Kelley'
;University of Missouri
United States of America
;
_audit_update_record             
;
2023-01-24 deposited with the CCDC.	2023-03-17 downloaded from the CCDC.
;
_audit_creation_date             2023-01-23
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H19 F N2 O'
_chemical_formula_sum            'C22 H19 F N2 O'
_chemical_formula_weight         346.39
_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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   6.5339(3)
_cell_length_b                   7.1569(3)
_cell_length_c                   37.6943(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1762.68(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9009
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.42
_cell_measurement_theta_min      2.90
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       pyramid
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_number            54595
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.551
_diffrn_reflns_theta_min         2.161
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Photon II CMOS area detector'
_diffrn_measurement_method       'shutterless omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Incoatec IMuS microfocus Mo tube'
_reflns_Friedel_coverage         0.970
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                4672
_reflns_number_total             5379
_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       'Bruker Apex4 V.2022.1-1/SAINT V8.40B'
_computing_data_collection       'Bruker Apex4 V.2022.1-1'
_computing_data_reduction        'Bruker Apex4 V.2022.1-1/SAINT V8.40B'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2050 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         5379
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.083
_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)+(0.0552P)²+0.6331P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1168
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups 
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.9571(2) 0.5018(2) 0.35330(4) 0.0256(3) Uani 1 1 d . . . . .
O1 O 0.3552(2) 0.4974(2) -0.00113(4) 0.0176(3) Uani 1 1 d . . . . .
N1 N 0.7182(3) 0.4477(3) 0.19236(5) 0.0174(4) Uani 1 1 d . . . . .
N2 N 0.6255(3) 0.4462(3) 0.15906(5) 0.0176(4) Uani 1 1 d . . . . .
C1 C 0.6922(3) 0.4982(3) 0.25389(5) 0.0134(4) Uani 1 1 d . . . . .
C2 C 0.8804(3) 0.4091(3) 0.25993(6) 0.0161(4) Uani 1 1 d . . . . .
H2 H 0.945(4) 0.349(4) 0.2411(8) 0.019 Uiso 1 1 d R . . . .
C3 C 0.9696(3) 0.4083(3) 0.29347(6) 0.0181(4) Uani 1 1 d . . . . .
H3 H 1.102(4) 0.347(4) 0.2983(8) 0.022 Uiso 1 1 d R . . . .
C4 C 0.8693(4) 0.4997(3) 0.32073(6) 0.0179(4) Uani 1 1 d . . . . .
C5 C 0.6852(4) 0.5906(3) 0.31605(6) 0.0182(4) Uani 1 1 d . . . . .
H5 H 0.622(4) 0.658(4) 0.3359(8) 0.022 Uiso 1 1 d R . . . .
C6 C 0.5972(4) 0.5889(3) 0.28237(6) 0.0169(4) Uani 1 1 d . . . . .
H6 H 0.472(5) 0.660(4) 0.2781(7) 0.020 Uiso 1 1 d R . . . .
C7 C 0.5996(3) 0.4974(3) 0.21792(6) 0.0146(4) Uani 1 1 d . . . . .
C8 C 0.3817(4) 0.5569(4) 0.21311(6) 0.0246(5) Uani 1 1 d . . . . .
H8A H 0.382(5) 0.689(5) 0.2091(9) 0.037 Uiso 1 1 d R . . . .
H8B H 0.298(6) 0.525(5) 0.2334(10) 0.037 Uiso 1 1 d R . . . .
H8C H 0.326(6) 0.492(5) 0.1925(10) 0.037 Uiso 1 1 d R . . . .
C9 C 0.7417(3) 0.4980(3) 0.13309(6) 0.0138(4) Uani 1 1 d . . . . .
C10 C 0.9581(4) 0.5625(4) 0.13760(7) 0.0235(5) Uani 1 1 d . . . . .
H10A H 0.966(5) 0.695(5) 0.1401(9) 0.035 Uiso 1 1 d R . . . .
H10B H 1.038(6) 0.530(5) 0.1161(10) 0.035 Uiso 1 1 d R . . . .
H10C H 1.014(6) 0.514(5) 0.1580(10) 0.035 Uiso 1 1 d R . . . .
C11 C 0.6467(3) 0.4970(3) 0.09746(5) 0.0137(4) Uani 1 1 d . . . . .
C12 C 0.4567(3) 0.4096(3) 0.09186(5) 0.0147(4) Uani 1 1 d . . . . .
H12 H 0.387(5) 0.347(4) 0.1126(7) 0.018 Uiso 1 1 d R . . . .
C13 C 0.3661(3) 0.4078(3) 0.05870(6) 0.0157(4) Uani 1 1 d . . . . .
H13 H 0.234(5) 0.344(4) 0.0544(8) 0.019 Uiso 1 1 d R . . . .
C14 C 0.4630(3) 0.4957(3) 0.03026(5) 0.0144(4) Uani 1 1 d . . . . .
C15 C 0.6506(3) 0.5862(3) 0.03508(6) 0.0169(4) Uani 1 1 d . . . . .
H15 H 0.715(4) 0.650(4) 0.0151(8) 0.020 Uiso 1 1 d R . . . .
C16 C 0.7405(3) 0.5855(3) 0.06854(6) 0.0163(4) Uani 1 1 d . . . . .
H16 H 0.875(4) 0.648(4) 0.0724(8) 0.020 Uiso 1 1 d R . . . .
C17 C 0.4562(3) 0.5011(3) -0.03371(6) 0.0154(4) Uani 1 1 d . . . . .
C18 C 0.6328(4) 0.3997(3) -0.04005(6) 0.0183(4) Uani 1 1 d . . . . .
H18 H 0.698(4) 0.328(4) -0.0218(8) 0.022 Uiso 1 1 d R . . . .
C19 C 0.7149(4) 0.3992(3) -0.07433(6) 0.0208(4) Uani 1 1 d . . . . .
H19 H 0.829(5) 0.325(4) -0.0797(7) 0.025 Uiso 1 1 d R . . . .
C20 C 0.6188(4) 0.4980(3) -0.10135(6) 0.0197(4) Uani 1 1 d . . . . .
H20 H 0.671(5) 0.497(4) -0.1234(9) 0.024 Uiso 1 1 d R . . . .
C21 C 0.4414(4) 0.5977(3) -0.09442(6) 0.0193(4) Uani 1 1 d . . . . .
H21 H 0.377(5) 0.666(4) -0.1131(8) 0.023 Uiso 1 1 d R . . . .
C22 C 0.3585(3) 0.6007(3) -0.06035(6) 0.0169(4) Uani 1 1 d . . . . .
H22 H 0.234(4) 0.666(4) -0.0546(7) 0.020 Uiso 1 1 d 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
F1 C4 1.355(2) . ?
O1 C14 1.377(3) . ?
O1 C17 1.394(3) . ?
N1 N2 1.394(2) . ?
N1 C7 1.286(3) . ?
N2 C9 1.293(3) . ?
C1 C2 1.404(3) . ?
C1 C6 1.400(3) . ?
C1 C7 1.485(3) . ?
C2 C3 1.392(3) . ?
C3 C4 1.383(3) . ?
C4 C5 1.379(3) . ?
C5 C6 1.394(3) . ?
C7 C8 1.497(3) . ?
C9 C10 1.496(3) . ?
C9 C11 1.480(3) . ?
C11 C12 1.406(3) . ?
C11 C16 1.402(3) . ?
C12 C13 1.383(3) . ?
C13 C14 1.395(3) . ?
C14 C15 1.398(3) . ?
C15 C16 1.391(3) . ?
C17 C18 1.384(3) . ?
C17 C22 1.387(3) . ?
C18 C19 1.399(3) . ?
C19 C20 1.390(3) . ?
C20 C21 1.386(3) . ?
C21 C22 1.394(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
C14 O1 C17 121.02(16) . . ?
C7 N1 N2 114.53(18) . . ?
C9 N2 N1 115.12(18) . . ?
C2 C1 C7 120.22(19) . . ?
C6 C1 C2 118.32(19) . . ?
C6 C1 C7 121.45(19) . . ?
C3 C2 C1 121.07(19) . . ?
C4 C3 C2 118.3(2) . . ?
F1 C4 C3 118.5(2) . . ?
F1 C4 C5 118.7(2) . . ?
C5 C4 C3 122.8(2) . . ?
C4 C5 C6 118.2(2) . . ?
C5 C6 C1 121.3(2) . . ?
N1 C7 C1 116.08(19) . . ?
N1 C7 C8 124.1(2) . . ?
C1 C7 C8 119.80(19) . . ?
N2 C9 C10 123.9(2) . . ?
N2 C9 C11 116.05(19) . . ?
C11 C9 C10 120.06(19) . . ?
C12 C11 C9 120.59(19) . . ?
C16 C11 C9 121.34(19) . . ?
C16 C11 C12 118.1(2) . . ?
C13 C12 C11 121.16(19) . . ?
C12 C13 C14 119.76(19) . . ?
O1 C14 C13 115.63(19) . . ?
O1 C14 C15 123.77(19) . . ?
C13 C14 C15 120.5(2) . . ?
C16 C15 C14 119.09(19) . . ?
C15 C16 C11 121.5(2) . . ?
C18 C17 O1 122.44(19) . . ?
C18 C17 C22 121.9(2) . . ?
C22 C17 O1 115.47(19) . . ?
C17 C18 C19 118.7(2) . . ?
C20 C19 C18 120.1(2) . . ?
C21 C20 C19 120.1(2) . . ?
C20 C21 C22 120.4(2) . . ?
C17 C22 C21 118.7(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_IIb
_audit_block_doi                 10.5517/ccdc.csd.cc28lgx8
_database_code_depnum_ccdc_archive 'CCDC 2103130'
loop_
_audit_author_name
_audit_author_address
'Steven Kelley'
;University of Missouri
United States of America
;
_audit_update_record             
;
2023-01-24 deposited with the CCDC.	2023-03-17 downloaded from the CCDC.
;
_audit_creation_date             2023-01-23
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H19 F N2 O'
_chemical_formula_sum            'C22 H19 F N2 O'
_chemical_formula_weight         346.39
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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                   6.5274(3)
_cell_length_b                   7.2009(3)
_cell_length_c                   37.7553(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1774.62(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9897
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      74.03
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   0.914
_shelx_estimated_absorpt_T_min   0.877
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.7019
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            29125
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.351
_diffrn_reflns_theta_min         2.340
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Incoatec IMuS microfocus Cu tube'
_reflns_Friedel_coverage         0.959
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                3516
_reflns_number_total             3568
_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       'Bruker Apex3 V.2018.1-0/SAINT V8.38A'
_computing_data_collection       'Bruker Apex3 V.2018.1-0'
_computing_data_reduction        'Bruker Apex3 V.2018.1-0/SAINT V8.38A'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1678 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3568
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0278
_refine_ls_restrained_S_all      1.064
_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)+(0.0491P)²+0.2159P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0783
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups 
2.a Aromatic/amide H refined with riding coordinates: 
 C2(H2), C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C15(H15), C16(H16), 
 C18(H18), C19(H19), C20(H20), C21(H21), C22(H22) 
2.b Idealised Me refined as rotating group: 
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
F1 F 0.95780(19) 0.50092(17) 0.35276(3) 0.0367(3) Uani 1 1 d . . . . .
O1 O 0.35499(18) 0.49664(18) -0.00084(3) 0.0255(3) Uani 1 1 d . . . . .
N1 N 0.7184(2) 0.4485(2) 0.19224(4) 0.0238(3) Uani 1 1 d . . . . .
N2 N 0.6255(2) 0.4473(2) 0.15901(4) 0.0244(3) Uani 1 1 d . . . . .
C1 C 0.6926(3) 0.4984(2) 0.25365(4) 0.0195(3) Uani 1 1 d . . . . .
C2 C 0.8808(2) 0.4101(2) 0.25968(4) 0.0229(3) Uani 1 1 d . . . . .
H2 H 0.948510 0.350005 0.240589 0.027 Uiso 1 1 calc R . . . .
C3 C 0.9701(3) 0.4090(2) 0.29308(4) 0.0260(4) Uani 1 1 d . . . . .
H3 H 1.096874 0.347746 0.297104 0.031 Uiso 1 1 calc R . . . .
C4 C 0.8698(3) 0.4991(2) 0.32024(5) 0.0260(4) Uani 1 1 d . . . . .
C5 C 0.6857(3) 0.5891(2) 0.31569(4) 0.0258(4) Uani 1 1 d . . . . .
H5 H 0.620674 0.650503 0.334912 0.031 Uiso 1 1 calc R . . . .
C6 C 0.5976(3) 0.5877(2) 0.28213(4) 0.0238(4) Uani 1 1 d . . . . .
H6 H 0.470200 0.648601 0.278499 0.029 Uiso 1 1 calc R . . . .
C7 C 0.6002(3) 0.4977(2) 0.21769(5) 0.0203(3) Uani 1 1 d . . . . .
C8 C 0.3816(3) 0.5571(3) 0.21305(5) 0.0325(4) Uani 1 1 d . . . . .
H8A H 0.376306 0.691407 0.209015 0.049 Uiso 1 1 calc GR . . . .
H8B H 0.303678 0.526222 0.234440 0.049 Uiso 1 1 calc GR . . . .
H8C H 0.322116 0.492324 0.192671 0.049 Uiso 1 1 calc GR . . . .
C9 C 0.7416(2) 0.4987(2) 0.13325(4) 0.0197(3) Uani 1 1 d . . . . .
C10 C 0.9586(3) 0.5625(3) 0.13766(5) 0.0323(4) Uani 1 1 d . . . . .
H10A H 0.961478 0.698141 0.139777 0.048 Uiso 1 1 calc GR . . . .
H10B H 1.039219 0.524418 0.117013 0.048 Uiso 1 1 calc GR . . . .
H10C H 1.016876 0.506789 0.159090 0.048 Uiso 1 1 calc GR . . . .
C11 C 0.6468(3) 0.4972(2) 0.09748(4) 0.0192(3) Uani 1 1 d . . . . .
C12 C 0.4567(2) 0.4101(2) 0.09191(4) 0.0208(3) Uani 1 1 d . . . . .
H12 H 0.389245 0.351798 0.111226 0.025 Uiso 1 1 calc R . . . .
C13 C 0.3666(3) 0.4079(2) 0.05887(4) 0.0221(3) Uani 1 1 d . . . . .
H13 H 0.239136 0.346881 0.055472 0.026 Uiso 1 1 calc R . . . .
C14 C 0.4632(3) 0.4956(2) 0.03047(4) 0.0206(3) Uani 1 1 d . . . . .
C15 C 0.6496(3) 0.5854(2) 0.03534(4) 0.0233(4) Uani 1 1 d . . . . .
H15 H 0.714428 0.646543 0.016065 0.028 Uiso 1 1 calc R . . . .
C16 C 0.7401(3) 0.5851(2) 0.06859(4) 0.0221(3) Uani 1 1 d . . . . .
H16 H 0.868043 0.645658 0.071819 0.027 Uiso 1 1 calc R . . . .
C17 C 0.4557(3) 0.5008(2) -0.03338(4) 0.0217(3) Uani 1 1 d . . . . .
C18 C 0.6326(3) 0.4002(2) -0.03978(5) 0.0263(4) Uani 1 1 d . . . . .
H18 H 0.697233 0.332570 -0.021295 0.032 Uiso 1 1 calc R . . . .
C19 C 0.7138(3) 0.4002(3) -0.07392(5) 0.0291(4) Uani 1 1 d . . . . .
H19 H 0.835684 0.332664 -0.078756 0.035 Uiso 1 1 calc R . . . .
C20 C 0.6183(3) 0.4978(2) -0.10080(5) 0.0281(4) Uani 1 1 d . . . . .
H20 H 0.674257 0.496817 -0.124033 0.034 Uiso 1 1 calc R . . . .
C21 C 0.4410(3) 0.5969(2) -0.09382(5) 0.0277(4) Uani 1 1 d . . . . .
H21 H 0.375370 0.663493 -0.112338 0.033 Uiso 1 1 calc R . . . .
C22 C 0.3586(3) 0.5996(2) -0.05986(5) 0.0244(3) Uani 1 1 d . . . . .
H22 H 0.237580 0.668211 -0.054958 0.029 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
F1 C4 1.3556(19) . ?
O1 C14 1.377(2) . ?
O1 C17 1.394(2) . ?
N1 N2 1.3933(17) . ?
N1 C7 1.282(2) . ?
N2 C9 1.287(2) . ?
C1 C2 1.402(2) . ?
C1 C6 1.398(2) . ?
C1 C7 1.486(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(3) . ?
C4 C5 1.376(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.499(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.498(2) . ?
C9 C11 1.485(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.406(2) . ?
C11 C16 1.401(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.379(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.395(2) . ?
C14 C15 1.390(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(2) . ?
C17 C22 1.381(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.394(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.383(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.385(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.391(2) . ?
C22 H22 0.9500 . ?

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 C17 120.98(13) . . ?
C7 N1 N2 114.49(13) . . ?
C9 N2 N1 114.99(13) . . ?
C2 C1 C7 120.19(15) . . ?
C6 C1 C2 118.19(15) . . ?
C6 C1 C7 121.61(15) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.19(15) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 120.9 . . ?
C4 C3 C2 118.24(15) . . ?
C4 C3 H3 120.9 . . ?
F1 C4 C3 118.48(16) . . ?
F1 C4 C5 118.60(16) . . ?
C5 C4 C3 122.91(16) . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.12(16) . . ?
C6 C5 H5 120.9 . . ?
C1 C6 H6 119.3 . . ?
C5 C6 C1 121.34(15) . . ?
C5 C6 H6 119.3 . . ?
N1 C7 C1 116.19(15) . . ?
N1 C7 C8 124.32(17) . . ?
C1 C7 C8 119.48(15) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C10 124.08(15) . . ?
N2 C9 C11 116.08(14) . . ?
C11 C9 C10 119.81(14) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C9 120.45(14) . . ?
C16 C11 C9 121.57(14) . . ?
C16 C11 C12 117.96(15) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.12(14) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.84(14) . . ?
C14 C13 H13 120.1 . . ?
O1 C14 C13 115.52(15) . . ?
O1 C14 C15 124.06(14) . . ?
C15 C14 C13 120.27(15) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.45(14) . . ?
C16 C15 H15 120.3 . . ?
C11 C16 H16 119.3 . . ?
C15 C16 C11 121.34(15) . . ?
C15 C16 H16 119.3 . . ?
C18 C17 O1 122.43(15) . . ?
C22 C17 O1 115.62(15) . . ?
C22 C17 C18 121.74(16) . . ?
C17 C18 H18 120.7 . . ?
C17 C18 C19 118.61(15) . . ?
C19 C18 H18 120.7 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.48(16) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 119.91(17) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 119.8 . . ?
C20 C21 C22 120.40(16) . . ?
C22 C21 H21 119.8 . . ?
C17 C22 C21 118.85(15) . . ?
C17 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?

_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_Ib
_audit_block_doi                 10.5517/ccdc.csd.cc25lhgr
_database_code_depnum_ccdc_archive 'CCDC 2013774'
loop_
_audit_author_name
_audit_author_address
'Steven Kelley'
;University of Missouri
United States of America
;
_audit_update_record             
;
2023-01-23 deposited with the CCDC.	2023-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H19 F N2 O'
_chemical_formula_sum            'C22 H19 F N2 O'
_chemical_formula_weight         346.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5322(15)
_cell_length_b                   7.3486(17)
_cell_length_c                   37.987(9)
_cell_angle_alpha                91.159(3)
_cell_angle_beta                 93.956(3)
_cell_angle_gamma                90.147(4)
_cell_volume                     1818.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1241
_cell_measurement_theta_min      3.23
_cell_measurement_theta_max      23.26

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      None
_exptl_crystal_density_method    None
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5234
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Smart-Apex CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17890
_diffrn_reflns_av_unetI/netI     0.0765
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         1.612
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6402
_reflns_number_gt                2860
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART V5.631 (Bruker, 2002)'
_computing_cell_refinement       'Bruker SAINT V7.60A (Bruker, 2008)'
_computing_data_reduction        'Bruker SAINT V7.60A (Bruker, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0911P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6402
_refine_ls_number_parameters     473
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1554
_refine_ls_R_factor_gt           0.0699
_refine_ls_wR_factor_ref         0.1995
_refine_ls_wR_factor_gt          0.1589
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_restrained_S_all      0.920
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.2878(4) 0.4648(3) 0.01344(5) 0.1049(8) Uani 1 1 d . . . . .
O1 O 0.4324(3) 0.4873(3) 0.36632(6) 0.0632(7) Uani 1 1 d . . . . .
N1 N -0.0068(4) 0.5159(4) 0.17430(7) 0.0568(8) Uani 1 1 d . . . . .
N2 N 0.0979(4) 0.5194(4) 0.20755(7) 0.0566(8) Uani 1 1 d . . . . .
C1 C -0.0010(5) 0.4635(4) 0.11328(8) 0.0459(8) Uani 1 1 d . . . . .
C2 C -0.1907(5) 0.5469(4) 0.10633(9) 0.0556(9) Uani 1 1 d . . . . .
H2 H -0.253928 0.603738 0.124768 0.067 Uiso 1 1 calc R U . . .
C3 C -0.2861(6) 0.5473(5) 0.07318(10) 0.0676(10) Uani 1 1 d . . . . .
H3 H -0.412222 0.604259 0.069076 0.081 Uiso 1 1 calc R U . . .
C4 C -0.1937(6) 0.4631(5) 0.04615(9) 0.0688(11) Uani 1 1 d . . . . .
C5 C -0.0093(6) 0.3780(5) 0.05126(9) 0.0714(11) Uani 1 1 d . . . . .
H5 H 0.050884 0.320519 0.032546 0.086 Uiso 1 1 calc R U . . .
C6 C 0.0867(5) 0.3789(5) 0.08498(9) 0.0615(10) Uani 1 1 d . . . . .
H6 H 0.212869 0.321582 0.088747 0.074 Uiso 1 1 calc R U . . .
C7 C 0.1016(5) 0.4654(4) 0.14911(8) 0.0479(8) Uani 1 1 d . . . . .
C8 C 0.3200(5) 0.4092(5) 0.15442(9) 0.0796(12) Uani 1 1 d . . . . .
H8A H 0.392590 0.444796 0.134509 0.119 Uiso 1 1 calc R U . . .
H8B H 0.327156 0.279494 0.156704 0.119 Uiso 1 1 calc R U . . .
H8C H 0.381315 0.467164 0.175458 0.119 Uiso 1 1 calc R U . . .
C9 C -0.0083(5) 0.4751(4) 0.23305(8) 0.0450(8) Uani 1 1 d . . . . .
C10 C -0.2272(5) 0.4147(5) 0.22850(9) 0.0743(11) Uani 1 1 d . . . . .
H10A H -0.290606 0.464960 0.207320 0.111 Uiso 1 1 calc R U . . .
H10B H -0.298584 0.456165 0.248402 0.111 Uiso 1 1 calc R U . . .
H10C H -0.233246 0.284270 0.226844 0.111 Uiso 1 1 calc R U . . .
C11 C 0.0986(5) 0.4800(4) 0.26834(8) 0.0443(8) Uani 1 1 d . . . . .
C12 C 0.2893(5) 0.5654(4) 0.27444(8) 0.0493(8) Uani 1 1 d . . . . .
H12 H 0.348095 0.620779 0.255771 0.059 Uiso 1 1 calc R U . . .
C13 C 0.3927(5) 0.5700(4) 0.30715(8) 0.0516(9) Uani 1 1 d . . . . .
H13 H 0.518887 0.629037 0.310352 0.062 Uiso 1 1 calc R U . . .
C14 C 0.3112(5) 0.4882(4) 0.33504(8) 0.0496(8) Uani 1 1 d . . . . .
C15 C 0.1233(5) 0.4001(4) 0.33012(9) 0.0582(9) Uani 1 1 d . . . . .
H15 H 0.067822 0.342430 0.348862 0.070 Uiso 1 1 calc R U . . .
C16 C 0.0192(5) 0.3983(4) 0.29734(8) 0.0537(9) Uani 1 1 d . . . . .
H16 H -0.108080 0.340823 0.294437 0.064 Uiso 1 1 calc R U . . .
C17 C 0.3477(5) 0.4884(4) 0.39873(8) 0.0513(8) Uani 1 1 d . . . . .
C18 C 0.1793(5) 0.5899(5) 0.40586(9) 0.0611(10) Uani 1 1 d . . . . .
H18 H 0.107949 0.653988 0.388095 0.073 Uiso 1 1 calc R U . . .
C19 C 0.1173(6) 0.5952(5) 0.43991(10) 0.0678(10) Uani 1 1 d . . . . .
H19 H 0.002841 0.663204 0.445036 0.081 Uiso 1 1 calc R U . . .
C20 C 0.2224(6) 0.5017(5) 0.46623(9) 0.0660(10) Uani 1 1 d . . . . .
H20 H 0.179815 0.505904 0.489098 0.079 Uiso 1 1 calc R U . . .
C21 C 0.3909(6) 0.4019(5) 0.45843(9) 0.0653(10) Uani 1 1 d . . . . .
H21 H 0.463811 0.339030 0.476197 0.078 Uiso 1 1 calc R U . . .
C22 C 0.4531(5) 0.3938(4) 0.42471(8) 0.0574(9) Uani 1 1 d . . . . .
H22 H 0.566414 0.324397 0.419537 0.069 Uiso 1 1 calc R U . . .
F2 F 0.2032(3) -0.0461(3) 0.01528(5) 0.0952(8) Uani 1 1 d . . . . .
O2 O 0.9346(3) -0.0138(3) 0.36711(6) 0.0639(7) Uani 1 1 d . . . . .
N3 N 0.4953(4) -0.0805(4) 0.17513(7) 0.0569(8) Uani 1 1 d . . . . .
N4 N 0.6005(4) -0.0790(4) 0.20834(7) 0.0573(7) Uani 1 1 d . . . . .
C23 C 0.5002(5) -0.0393(4) 0.11428(8) 0.0466(8) Uani 1 1 d . . . . .
C24 C 0.3105(5) -0.1250(4) 0.10731(9) 0.0561(9) Uani 1 1 d . . . . .
H24 H 0.249418 -0.181643 0.125604 0.067 Uiso 1 1 calc R U . . .
C25 C 0.2121(5) -0.1282(5) 0.07446(9) 0.0637(10) Uani 1 1 d . . . . .
H25 H 0.086288 -0.187047 0.070369 0.076 Uiso 1 1 calc R U . . .
C26 C 0.3003(6) -0.0442(5) 0.04785(9) 0.0650(10) Uani 1 1 d . . . . .
C27 C 0.4849(6) 0.0423(5) 0.05277(9) 0.0711(11) Uani 1 1 d . . . . .
H27 H 0.542823 0.099039 0.034159 0.085 Uiso 1 1 calc R U . . .
C28 C 0.5843(5) 0.0437(5) 0.08618(9) 0.0613(10) Uani 1 1 d . . . . .
H28 H 0.710843 0.101861 0.089846 0.074 Uiso 1 1 calc R U . . .
C29 C 0.6044(5) -0.0366(4) 0.14997(8) 0.0478(8) Uani 1 1 d . . . . .
C30 C 0.8253(5) 0.0181(5) 0.15523(9) 0.0776(12) Uani 1 1 d . . . . .
H30A H 0.895028 -0.016532 0.134704 0.116 Uiso 1 1 calc R U . . .
H30B H 0.887564 -0.041751 0.175476 0.116 Uiso 1 1 calc R U . . .
H30C H 0.835083 0.147524 0.158882 0.116 Uiso 1 1 calc R U . . .
C31 C 0.4946(5) -0.0265(4) 0.23401(8) 0.0456(8) Uani 1 1 d . . . . .
C32 C 0.2791(5) 0.0348(5) 0.22913(9) 0.0733(11) Uani 1 1 d . . . . .
H32A H 0.276212 0.164159 0.226098 0.110 Uiso 1 1 calc R U . . .
H32B H 0.207852 0.004748 0.249520 0.110 Uiso 1 1 calc R U . . .
H32C H 0.213567 -0.024724 0.208612 0.110 Uiso 1 1 calc R U . . .
C33 C 0.6015(5) -0.0250(4) 0.26943(8) 0.0432(8) Uani 1 1 d . . . . .
C34 C 0.5222(5) 0.0617(4) 0.29818(8) 0.0528(9) Uani 1 1 d . . . . .
H34 H 0.395410 0.118712 0.295266 0.063 Uiso 1 1 calc R U . . .
C35 C 0.6265(5) 0.0658(4) 0.33102(8) 0.0571(9) Uani 1 1 d . . . . .
H35 H 0.571555 0.126921 0.349840 0.068 Uiso 1 1 calc R U . . .
C36 C 0.8131(5) -0.0215(4) 0.33579(8) 0.0474(8) Uani 1 1 d . . . . .
C37 C 0.8958(5) -0.1075(4) 0.30784(8) 0.0514(8) Uani 1 1 d . . . . .
H37 H 1.021853 -0.165573 0.310991 0.062 Uiso 1 1 calc R U . . .
C38 C 0.7922(5) -0.1080(4) 0.27512(8) 0.0480(8) Uani 1 1 d . . . . .
H38 H 0.850939 -0.165317 0.256246 0.058 Uiso 1 1 calc R U . . .
C39 C 0.8510(5) -0.0069(4) 0.39941(8) 0.0511(8) Uani 1 1 d . . . . .
C40 C 0.6809(5) -0.1080(5) 0.40633(9) 0.0632(10) Uani 1 1 d . . . . .
H40 H 0.610049 -0.175888 0.388476 0.076 Uiso 1 1 calc R U . . .
C41 C 0.6176(6) -0.1064(5) 0.44034(10) 0.0709(11) Uani 1 1 d . . . . .
H41 H 0.502419 -0.173387 0.445306 0.085 Uiso 1 1 calc R U . . .
C42 C 0.7220(5) -0.0076(5) 0.46684(9) 0.0648(10) Uani 1 1 d . . . . .
H42 H 0.679034 -0.008319 0.489669 0.078 Uiso 1 1 calc R U . . .
C43 C 0.8905(6) 0.0921(5) 0.45932(9) 0.0653(10) Uani 1 1 d . . . . .
H43 H 0.961616 0.160218 0.477116 0.078 Uiso 1 1 calc R U . . .
C44 C 0.9551(5) 0.0921(4) 0.42565(9) 0.0582(9) Uani 1 1 d . . . . .
H44 H 1.069851 0.159778 0.420747 0.070 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
F1 C4 1.348(4) . ?
O1 C14 1.382(3) . ?
O1 C17 1.384(4) . ?
N1 C7 1.279(4) . ?
N1 N2 1.394(3) . ?
N2 C9 1.277(4) . ?
C1 C6 1.389(4) . ?
C1 C2 1.395(4) . ?
C1 C7 1.475(4) . ?
C2 C3 1.366(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.365(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.363(5) . ?
C5 C6 1.387(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.488(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C11 1.468(4) . ?
C9 C10 1.494(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C16 1.395(4) . ?
C11 C12 1.396(4) . ?
C12 C13 1.372(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.367(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.386(4) . ?
C15 C16 1.377(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C22 1.367(4) . ?
C17 C18 1.370(4) . ?
C18 C19 1.382(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.371(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.370(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.371(4) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
F2 C26 1.351(3) . ?
O2 C39 1.377(4) . ?
O2 C36 1.384(3) . ?
N3 C29 1.277(4) . ?
N3 N4 1.394(3) . ?
N4 C31 1.288(4) . ?
C23 C28 1.385(4) . ?
C23 C24 1.395(4) . ?
C23 C29 1.474(4) . ?
C24 C25 1.363(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.356(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.361(5) . ?
C27 C28 1.385(4) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 C30 1.496(4) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 C33 1.473(4) . ?
C31 C32 1.479(4) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34 1.385(4) . ?
C33 C38 1.394(4) . ?
C34 C35 1.379(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.381(4) . ?
C35 H35 0.9300 . ?
C36 C37 1.368(4) . ?
C37 C38 1.373(4) . ?
C37 H37 0.9300 . ?
C38 H38 0.9300 . ?
C39 C44 1.364(4) . ?
C39 C40 1.378(4) . ?
C40 C41 1.384(4) . ?
C40 H40 0.9300 . ?
C41 C42 1.371(4) . ?
C41 H41 0.9300 . ?
C42 C43 1.370(5) . ?
C42 H42 0.9300 . ?
C43 C44 1.374(4) . ?
C43 H43 0.9300 . ?
C44 H44 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
C14 O1 C17 121.6(3) . . ?
C7 N1 N2 114.5(3) . . ?
C9 N2 N1 115.4(3) . . ?
C6 C1 C2 117.1(3) . . ?
C6 C1 C7 121.6(3) . . ?
C2 C1 C7 121.4(3) . . ?
C3 C2 C1 121.8(3) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C4 C3 C2 119.1(4) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
F1 C4 C5 119.2(4) . . ?
F1 C4 C3 118.9(4) . . ?
C5 C4 C3 122.0(3) . . ?
C4 C5 C6 118.5(3) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C5 C6 C1 121.6(3) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
N1 C7 C1 116.6(3) . . ?
N1 C7 C8 123.5(3) . . ?
C1 C7 C8 119.9(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C11 116.3(3) . . ?
N2 C9 C10 123.8(3) . . ?
C11 C9 C10 119.9(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 116.3(3) . . ?
C16 C11 C9 122.6(3) . . ?
C12 C11 C9 121.1(3) . . ?
C13 C12 C11 122.0(3) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 O1 116.5(3) . . ?
C13 C14 C15 119.6(3) . . ?
O1 C14 C15 123.7(3) . . ?
C16 C15 C14 119.7(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C11 122.0(3) . . ?
C15 C16 H16 119.0 . . ?
C11 C16 H16 119.0 . . ?
C22 C17 C18 120.9(3) . . ?
C22 C17 O1 115.8(3) . . ?
C18 C17 O1 123.1(3) . . ?
C17 C18 C19 118.8(3) . . ?
C17 C18 H18 120.6 . . ?
C19 C18 H18 120.6 . . ?
C20 C19 C18 120.9(4) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C21 C20 C19 119.2(3) . . ?
C21 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
C20 C21 C22 120.6(3) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C17 C22 C21 119.6(3) . . ?
C17 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C39 O2 C36 121.8(3) . . ?
C29 N3 N4 114.5(3) . . ?
C31 N4 N3 115.1(3) . . ?
C28 C23 C24 116.8(3) . . ?
C28 C23 C29 121.9(3) . . ?
C24 C23 C29 121.3(3) . . ?
C25 C24 C23 121.9(3) . . ?
C25 C24 H24 119.0 . . ?
C23 C24 H24 119.0 . . ?
C26 C25 C24 119.0(3) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
F2 C26 C25 119.4(3) . . ?
F2 C26 C27 118.5(4) . . ?
C25 C26 C27 122.2(3) . . ?
C26 C27 C28 118.4(3) . . ?
C26 C27 H27 120.8 . . ?
C28 C27 H27 120.8 . . ?
C23 C28 C27 121.7(3) . . ?
C23 C28 H28 119.1 . . ?
C27 C28 H28 119.1 . . ?
N3 C29 C23 116.3(3) . . ?
N3 C29 C30 123.6(3) . . ?
C23 C29 C30 120.1(3) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N4 C31 C33 116.3(3) . . ?
N4 C31 C32 123.4(3) . . ?
C33 C31 C32 120.4(3) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C34 C33 C38 117.0(3) . . ?
C34 C33 C31 122.3(3) . . ?
C38 C33 C31 120.6(3) . . ?
C35 C34 C33 121.7(3) . . ?
C35 C34 H34 119.2 . . ?
C33 C34 H34 119.2 . . ?
C34 C35 C36 119.6(3) . . ?
C34 C35 H35 120.2 . . ?
C36 C35 H35 120.2 . . ?
C37 C36 C35 120.0(3) . . ?
C37 C36 O2 116.3(3) . . ?
C35 C36 O2 123.4(3) . . ?
C36 C37 C38 119.9(3) . . ?
C36 C37 H37 120.1 . . ?
C38 C37 H37 120.1 . . ?
C37 C38 C33 121.8(3) . . ?
C37 C38 H38 119.1 . . ?
C33 C38 H38 119.1 . . ?
C44 C39 O2 116.9(3) . . ?
C44 C39 C40 120.5(3) . . ?
O2 C39 C40 122.3(3) . . ?
C39 C40 C41 118.7(3) . . ?
C39 C40 H40 120.6 . . ?
C41 C40 H40 120.6 . . ?
C42 C41 C40 121.0(4) . . ?
C42 C41 H41 119.5 . . ?
C40 C41 H41 119.5 . . ?
C43 C42 C41 119.3(3) . . ?
C43 C42 H42 120.4 . . ?
C41 C42 H42 120.4 . . ?
C42 C43 C44 120.4(3) . . ?
C42 C43 H43 119.8 . . ?
C44 C43 H43 119.8 . . ?
C39 C44 C43 120.1(3) . . ?
C39 C44 H44 120.0 . . ?
C43 C44 H44 120.0 . . ?

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
C7 N1 N2 C9 -145.0(3) . . . . ?
C6 C1 C2 C3 -0.5(5) . . . . ?
C7 C1 C2 C3 179.4(3) . . . . ?
C1 C2 C3 C4 0.3(5) . . . . ?
C2 C3 C4 F1 -179.6(3) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
F1 C4 C5 C6 179.3(3) . . . . ?
C3 C4 C5 C6 -0.5(6) . . . . ?
C4 C5 C6 C1 0.2(5) . . . . ?
C2 C1 C6 C5 0.3(5) . . . . ?
C7 C1 C6 C5 -179.7(3) . . . . ?
N2 N1 C7 C1 -178.7(2) . . . . ?
N2 N1 C7 C8 1.7(4) . . . . ?
C6 C1 C7 N1 -167.4(3) . . . . ?
C2 C1 C7 N1 12.7(4) . . . . ?
C6 C1 C7 C8 12.3(4) . . . . ?
C2 C1 C7 C8 -167.6(3) . . . . ?
N1 N2 C9 C11 -179.3(2) . . . . ?
N1 N2 C9 C10 2.7(4) . . . . ?
N2 C9 C11 C16 -165.5(3) . . . . ?
C10 C9 C11 C16 12.6(4) . . . . ?
N2 C9 C11 C12 13.4(4) . . . . ?
C10 C9 C11 C12 -168.5(3) . . . . ?
C16 C11 C12 C13 -0.4(4) . . . . ?
C9 C11 C12 C13 -179.4(3) . . . . ?
C11 C12 C13 C14 0.6(5) . . . . ?
C12 C13 C14 O1 175.2(3) . . . . ?
C12 C13 C14 C15 0.1(5) . . . . ?
C17 O1 C14 C13 150.2(3) . . . . ?
C17 O1 C14 C15 -35.0(4) . . . . ?
C13 C14 C15 C16 -1.1(5) . . . . ?
O1 C14 C15 C16 -175.7(3) . . . . ?
C14 C15 C16 C11 1.3(5) . . . . ?
C12 C11 C16 C15 -0.5(5) . . . . ?
C9 C11 C16 C15 178.4(3) . . . . ?
C14 O1 C17 C22 146.0(3) . . . . ?
C14 O1 C17 C18 -39.6(4) . . . . ?
C22 C17 C18 C19 0.0(5) . . . . ?
O1 C17 C18 C19 -174.1(3) . . . . ?
C17 C18 C19 C20 0.3(5) . . . . ?
C18 C19 C20 C21 0.0(6) . . . . ?
C19 C20 C21 C22 -0.6(5) . . . . ?
C18 C17 C22 C21 -0.6(5) . . . . ?
O1 C17 C22 C21 173.9(3) . . . . ?
C20 C21 C22 C17 1.0(5) . . . . ?
C29 N3 N4 C31 144.6(3) . . . . ?
C28 C23 C24 C25 0.3(5) . . . . ?
C29 C23 C24 C25 179.8(3) . . . . ?
C23 C24 C25 C26 -0.6(5) . . . . ?
C24 C25 C26 F2 -179.7(3) . . . . ?
C24 C25 C26 C27 0.5(6) . . . . ?
F2 C26 C27 C28 -179.9(3) . . . . ?
C25 C26 C27 C28 0.0(6) . . . . ?
C24 C23 C28 C27 0.2(5) . . . . ?
C29 C23 C28 C27 -179.3(3) . . . . ?
C26 C27 C28 C23 -0.3(5) . . . . ?
N4 N3 C29 C23 179.0(2) . . . . ?
N4 N3 C29 C30 -1.8(4) . . . . ?
C28 C23 C29 N3 165.0(3) . . . . ?
C24 C23 C29 N3 -14.5(4) . . . . ?
C28 C23 C29 C30 -14.2(5) . . . . ?
C24 C23 C29 C30 166.3(3) . . . . ?
N3 N4 C31 C33 179.5(2) . . . . ?
N3 N4 C31 C32 -2.2(4) . . . . ?
N4 C31 C33 C34 166.6(3) . . . . ?
C32 C31 C33 C34 -11.7(4) . . . . ?
N4 C31 C33 C38 -11.6(4) . . . . ?
C32 C31 C33 C38 170.1(3) . . . . ?
C38 C33 C34 C35 -0.1(4) . . . . ?
C31 C33 C34 C35 -178.4(3) . . . . ?
C33 C34 C35 C36 -1.3(5) . . . . ?
C34 C35 C36 C37 1.6(5) . . . . ?
C34 C35 C36 O2 175.4(3) . . . . ?
C39 O2 C36 C37 -151.3(3) . . . . ?
C39 O2 C36 C35 34.7(4) . . . . ?
C35 C36 C37 C38 -0.4(5) . . . . ?
O2 C36 C37 C38 -174.7(3) . . . . ?
C36 C37 C38 C33 -1.0(5) . . . . ?
C34 C33 C38 C37 1.3(4) . . . . ?
C31 C33 C38 C37 179.6(3) . . . . ?
C36 O2 C39 C44 -146.0(3) . . . . ?
C36 O2 C39 C40 39.9(4) . . . . ?
C44 C39 C40 C41 0.2(5) . . . . ?
O2 C39 C40 C41 174.1(3) . . . . ?
C39 C40 C41 C42 -0.5(5) . . . . ?
C40 C41 C42 C43 0.6(6) . . . . ?
C41 C42 C43 C44 -0.5(5) . . . . ?
O2 C39 C44 C43 -174.3(3) . . . . ?
C40 C39 C44 C43 -0.1(5) . . . . ?
C42 C43 C44 C39 0.2(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C8 H8C N2 0.96 2.31 2.679(4) 101.7 . yes
C10 H10A N1 0.96 2.34 2.708(4) 101.8 . yes
C30 H30B N4 0.96 2.34 2.683(4) 100.1 . yes
C32 H32C N3 0.96 2.34 2.694(4) 101.0 . yes
C27 H27 F2 0.93 2.61 3.401(4) 142.6 2_655 yes

_refine_diff_density_max         0.271
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.056



####################################################################### 
# 
# 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_Ia
_audit_block_doi                 10.5517/ccdc.csd.cc25lhfq
_database_code_depnum_ccdc_archive 'CCDC 2013773'
loop_
_audit_author_name
_audit_author_address
'Steven Kelley'
;University of Missouri
United States of America
;
_audit_update_record             
;
2023-01-23 deposited with the CCDC.	2023-03-17 downloaded from the CCDC.
;
_audit_creation_date             2023-01-23
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H19 F N2 O'
_chemical_formula_sum            'C22 H19 F N2 O'
_chemical_formula_weight         346.39
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5410(2)
_cell_length_b                   7.1465(2)
_cell_length_c                   37.8014(10)
_cell_angle_alpha                91.0820(12)
_cell_angle_beta                 94.0970(12)
_cell_angle_gamma                90.1522(13)
_cell_volume                     1762.19(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.14
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   0.945
_shelx_estimated_absorpt_T_min   0.859
_exptl_absorpt_coefficient_mu    0.712
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            55830
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.315
_diffrn_reflns_theta_min         2.344
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker X8 Prospector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'ImuS microfocus source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5901
_reflns_number_total             6917
_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       'Bruker Apex3 V.2018.1-0/SAINT V8.38A'
_computing_data_collection       'Bruker Apex3 V.2018.1-0'
_computing_data_reduction        'Bruker Apex3 V.2018.1-0/SAINT V8.38A'
_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         0.244
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     575
_refine_ls_number_reflns         6917
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0579
_refine_ls_restrained_S_all      1.197
_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)+(0.0500P)²+2.4293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1607
_refine_ls_wR_factor_ref         0.1644
_refine_special_details          ?
_olex2_refinement_description    
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups, All C(H,H,H,H,H,H,H,H,H) groups 
2.a Idealised Me refined as rotating group: 
 C32(H32A,H32B,H32C) 
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
F1 F -0.2884(2) 0.4588(2) 0.01070(4) 0.0296(3) Uani 1 1 d . . . . .
F2 F 0.1990(2) -0.0449(2) 0.01310(4) 0.0268(3) Uani 1 1 d . . . . .
O1 O 0.4332(2) 0.4856(2) 0.36673(4) 0.0194(3) Uani 1 1 d . . . . .
O2 O 0.9361(2) -0.0123(2) 0.36755(4) 0.0191(3) Uani 1 1 d . . . . .
N1 N -0.0099(3) 0.5190(3) 0.17336(5) 0.0185(4) Uani 1 1 d . . . . .
N2 N 0.0951(3) 0.5242(3) 0.20675(5) 0.0185(4) Uani 1 1 d . . . . .
N3 N 0.4938(3) -0.0862(3) 0.17432(5) 0.0190(4) Uani 1 1 d . . . . .
N4 N 0.5989(3) -0.0854(3) 0.20772(5) 0.0187(4) Uani 1 1 d . . . . .
C1 C -0.0049(3) 0.4619(3) 0.11163(6) 0.0164(4) Uani 1 1 d . . . . .
C2 C -0.1940(3) 0.5493(3) 0.10476(6) 0.0181(5) Uani 1 1 d . . . . .
H2 H -0.263(4) 0.618(4) 0.1237(7) 0.022 Uiso 1 1 d R . . . .
C3 C -0.2907(4) 0.5493(3) 0.07088(6) 0.0210(5) Uani 1 1 d . . . . .
H3 H -0.424(5) 0.607(4) 0.0655(7) 0.025 Uiso 1 1 d R . . . .
C4 C -0.1952(4) 0.4590(3) 0.04388(6) 0.0209(5) Uani 1 1 d . . . . .
C5 C -0.0105(4) 0.3692(3) 0.04940(6) 0.0211(5) Uani 1 1 d . . . . .
H5 H 0.048(4) 0.299(4) 0.0300(8) 0.025 Uiso 1 1 d R . . . .
C6 C 0.0846(4) 0.3716(3) 0.08352(6) 0.0194(5) Uani 1 1 d . . . . .
H6 H 0.209(4) 0.307(4) 0.0869(7) 0.023 Uiso 1 1 d R . . . .
C7 C 0.0986(3) 0.4658(3) 0.14803(6) 0.0162(4) Uani 1 1 d . . . . .
C8 C 0.3185(4) 0.4056(4) 0.15329(7) 0.0264(5) Uani 1 1 d . . . . .
C9 C -0.0113(3) 0.4758(3) 0.23253(6) 0.0159(4) Uani 1 1 d . . . . .
C10 C -0.2297(4) 0.4115(4) 0.22801(7) 0.0255(5) Uani 1 1 d . . . . .
C11 C 0.0980(3) 0.4809(3) 0.26843(6) 0.0159(4) Uani 1 1 d . . . . .
C12 C 0.2904(3) 0.5690(3) 0.27395(6) 0.0166(4) Uani 1 1 d . . . . .
H12 H 0.348(4) 0.632(4) 0.2528(7) 0.020 Uiso 1 1 d R . . . .
C13 C 0.3943(3) 0.5731(3) 0.30708(6) 0.0169(4) Uani 1 1 d . . . . .
H13 H 0.531(4) 0.632(4) 0.3115(7) 0.020 Uiso 1 1 d R . . . .
C14 C 0.3095(3) 0.4877(3) 0.33539(6) 0.0163(4) Uani 1 1 d . . . . .
C15 C 0.1209(4) 0.3982(3) 0.33072(6) 0.0185(5) Uani 1 1 d . . . . .
H15 H 0.065(4) 0.336(4) 0.3512(7) 0.022 Uiso 1 1 d R . . . .
C16 C 0.0157(4) 0.3961(3) 0.29725(6) 0.0187(5) Uani 1 1 d . . . . .
H16 H -0.116(4) 0.334(4) 0.2940(7) 0.022 Uiso 1 1 d R . . . .
C17 C 0.3482(3) 0.4866(3) 0.39940(6) 0.0157(4) Uani 1 1 d . . . . .
C18 C 0.1759(4) 0.5919(3) 0.40627(6) 0.0182(5) Uani 1 1 d . . . . .
H18 H 0.104(4) 0.659(4) 0.3878(7) 0.022 Uiso 1 1 d R . . . .
C19 C 0.1134(4) 0.5983(3) 0.44080(6) 0.0202(5) Uani 1 1 d . . . . .
H19 H -0.003(4) 0.675(4) 0.4456(7) 0.024 Uiso 1 1 d R . . . .
C20 C 0.2215(4) 0.5026(3) 0.46770(6) 0.0196(5) Uani 1 1 d . . . . .
H20 H 0.178(4) 0.514(4) 0.4929(8) 0.023 Uiso 1 1 d R . . . .
C21 C 0.3920(4) 0.3979(3) 0.46009(6) 0.0186(5) Uani 1 1 d . . . . .
H21 H 0.465(4) 0.322(4) 0.4789(7) 0.022 Uiso 1 1 d R . . . .
C22 C 0.4562(3) 0.3893(3) 0.42588(6) 0.0176(5) Uani 1 1 d . . . . .
H22 H 0.574(4) 0.318(4) 0.4204(7) 0.021 Uiso 1 1 d R . . . .
C23 C 0.4979(3) -0.0416(3) 0.11281(6) 0.0157(4) Uani 1 1 d . . . . .
C24 C 0.3080(4) -0.1324(3) 0.10623(6) 0.0181(5) Uani 1 1 d . . . . .
H24 H 0.248(4) -0.193(4) 0.1255(7) 0.022 Uiso 1 1 d R . . . .
C25 C 0.2074(4) -0.1350(3) 0.07266(6) 0.0201(5) Uani 1 1 d . . . . .
H25 H 0.086(5) -0.195(4) 0.0682(7) 0.024 Uiso 1 1 d R . . . .
C26 C 0.2983(4) -0.0444(3) 0.04583(6) 0.0193(5) Uani 1 1 d . . . . .
C27 C 0.4819(4) 0.0490(3) 0.05110(6) 0.0208(5) Uani 1 1 d . . . . .
H27 H 0.537(4) 0.110(4) 0.0314(8) 0.025 Uiso 1 1 d R . . . .
C28 C 0.5827(4) 0.0484(3) 0.08478(6) 0.0194(5) Uani 1 1 d . . . . .
H28 H 0.715(4) 0.117(4) 0.0893(7) 0.023 Uiso 1 1 d R . . . .
C29 C 0.6028(3) -0.0403(3) 0.14895(6) 0.0163(4) Uani 1 1 d . . . . .
C30 C 0.8252(4) 0.0169(4) 0.15405(7) 0.0258(5) Uani 1 1 d . . . . .
C31 C 0.4930(3) -0.0297(3) 0.23336(6) 0.0165(4) Uani 1 1 d . . . . .
C32 C 0.2763(4) 0.0366(4) 0.22868(6) 0.0251(5) Uani 1 1 d . . . . .
H32A H 0.208860 -0.021683 0.207246 0.038 Uiso 1 1 calc GR . . . .
H32B H 0.275005 0.172995 0.226400 0.038 Uiso 1 1 calc GR . . . .
H32C H 0.203135 0.002044 0.249344 0.038 Uiso 1 1 calc GR . . . .
C33 C 0.6022(3) -0.0267(3) 0.26920(6) 0.0156(4) Uani 1 1 d . . . . .
C34 C 0.5200(4) 0.0636(3) 0.29811(6) 0.0188(5) Uani 1 1 d . . . . .
H34 H 0.390(4) 0.122(4) 0.2945(7) 0.023 Uiso 1 1 d R . . . .
C35 C 0.6246(4) 0.0692(3) 0.33152(6) 0.0185(5) Uani 1 1 d . . . . .
H35 H 0.572(4) 0.139(4) 0.3519(7) 0.022 Uiso 1 1 d R . . . .
C36 C 0.8128(3) -0.0198(3) 0.33619(6) 0.0163(4) Uani 1 1 d . . . . .
C37 C 0.8984(3) -0.1109(3) 0.30788(6) 0.0170(4) Uani 1 1 d . . . . .
H37 H 1.034(4) -0.172(4) 0.3132(7) 0.020 Uiso 1 1 d R . . . .
C38 C 0.7936(3) -0.1129(3) 0.27478(6) 0.0167(4) Uani 1 1 d . . . . .
H38 H 0.857(4) -0.167(4) 0.2548(7) 0.020 Uiso 1 1 d R . . . .
C39 C 0.8497(3) -0.0070(3) 0.40013(6) 0.0156(4) Uani 1 1 d . . . . .
C40 C 0.6772(4) -0.1108(3) 0.40693(6) 0.0187(5) Uani 1 1 d . . . . .
H40 H 0.605(4) -0.189(4) 0.3885(7) 0.022 Uiso 1 1 d R . . . .
C41 C 0.6133(4) -0.1105(3) 0.44122(6) 0.0209(5) Uani 1 1 d . . . . .
H41 H 0.492(4) -0.182(4) 0.4472(7) 0.025 Uiso 1 1 d R . . . .
C42 C 0.7203(4) -0.0076(3) 0.46820(6) 0.0195(5) Uani 1 1 d . . . . .
H8A H 0.328(5) 0.267(5) 0.1557(8) 0.029 Uiso 1 1 d R . . . .
H8B H 0.370(5) 0.467(4) 0.1735(8) 0.029 Uiso 1 1 d R . . . .
H8C H 0.397(5) 0.439(4) 0.1326(8) 0.029 Uiso 1 1 d R . . . .
H10A H -0.238(5) 0.276(5) 0.2264(8) 0.029 Uiso 1 1 d R . . . .
H10B H -0.295(5) 0.469(4) 0.2072(8) 0.029 Uiso 1 1 d R . . . .
H10C H -0.308(5) 0.449(4) 0.2484(8) 0.029 Uiso 1 1 d R . . . .
H30A H 0.887(5) -0.051(4) 0.1747(8) 0.029 Uiso 1 1 d R . . . .
H30B H 0.834(5) 0.148(5) 0.1574(8) 0.029 Uiso 1 1 d R . . . .
H30C H 0.902(5) -0.013(4) 0.1330(8) 0.029 Uiso 1 1 d R . . . .
H42 H 0.679(4) -0.010(4) 0.4929(8) 0.023 Uiso 1 1 d R . . . .
C43 C 0.8908(4) 0.0962(3) 0.46085(6) 0.0188(5) Uani 1 1 d . . . . .
H43 H 0.967(4) 0.169(4) 0.4800(7) 0.023 Uiso 1 1 d R . . . .
C44 C 0.9572(4) 0.0976(3) 0.42664(6) 0.0177(4) Uani 1 1 d . . . . .
H44 H 1.074(4) 0.171(4) 0.4207(7) 0.021 Uiso 1 1 d 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
F1 C4 1.355(3) . ?
F2 C26 1.356(3) . ?
O1 C14 1.386(3) . ?
O1 C17 1.390(3) . ?
O2 C36 1.385(3) . ?
O2 C39 1.392(3) . ?
N1 N2 1.393(3) . ?
N1 C7 1.285(3) . ?
N2 C9 1.289(3) . ?
N3 N4 1.394(3) . ?
N3 C29 1.282(3) . ?
N4 C31 1.288(3) . ?
C1 C2 1.397(3) . ?
C1 C6 1.397(3) . ?
C1 C7 1.489(3) . ?
C2 C3 1.387(3) . ?
C3 C4 1.385(3) . ?
C4 C5 1.374(3) . ?
C5 C6 1.391(3) . ?
C7 C8 1.503(3) . ?
C9 C10 1.497(3) . ?
C9 C11 1.488(3) . ?
C11 C12 1.406(3) . ?
C11 C16 1.396(3) . ?
C12 C13 1.382(3) . ?
C13 C14 1.390(3) . ?
C14 C15 1.387(3) . ?
C15 C16 1.396(3) . ?
C17 C18 1.394(3) . ?
C17 C22 1.383(3) . ?
C18 C19 1.395(3) . ?
C19 C20 1.389(3) . ?
C20 C21 1.389(3) . ?
C21 C22 1.388(3) . ?
C23 C24 1.404(3) . ?
C23 C28 1.397(3) . ?
C23 C29 1.484(3) . ?
C24 C25 1.387(3) . ?
C25 C26 1.382(3) . ?
C26 C27 1.372(3) . ?
C27 C28 1.391(3) . ?
C29 C30 1.508(3) . ?
C31 C32 1.495(3) . ?
C31 C33 1.486(3) . ?
C33 C34 1.400(3) . ?
C33 C38 1.401(3) . ?
C34 C35 1.393(3) . ?
C35 C36 1.389(3) . ?
C36 C37 1.394(3) . ?
C37 C38 1.383(3) . ?
C39 C40 1.391(3) . ?
C39 C44 1.388(3) . ?
C40 C41 1.390(3) . ?
C41 C42 1.392(3) . ?
C42 C43 1.385(3) . ?
C43 C44 1.394(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
C14 O1 C17 120.85(17) . . ?
C36 O2 C39 120.58(17) . . ?
C7 N1 N2 114.46(19) . . ?
C9 N2 N1 115.10(19) . . ?
C29 N3 N4 114.60(19) . . ?
C31 N4 N3 114.83(19) . . ?
C2 C1 C6 118.4(2) . . ?
C2 C1 C7 120.6(2) . . ?
C6 C1 C7 121.0(2) . . ?
C3 C2 C1 121.3(2) . . ?
C4 C3 C2 118.2(2) . . ?
F1 C4 C3 118.5(2) . . ?
F1 C4 C5 118.8(2) . . ?
C5 C4 C3 122.7(2) . . ?
C4 C5 C6 118.3(2) . . ?
C5 C6 C1 121.2(2) . . ?
N1 C7 C1 116.7(2) . . ?
N1 C7 C8 124.0(2) . . ?
C1 C7 C8 119.3(2) . . ?
N2 C9 C10 124.2(2) . . ?
N2 C9 C11 115.9(2) . . ?
C11 C9 C10 119.9(2) . . ?
C12 C11 C9 120.3(2) . . ?
C16 C11 C9 121.5(2) . . ?
C16 C11 C12 118.2(2) . . ?
C13 C12 C11 120.8(2) . . ?
C12 C13 C14 119.9(2) . . ?
O1 C14 C13 115.4(2) . . ?
O1 C14 C15 123.8(2) . . ?
C15 C14 C13 120.6(2) . . ?
C14 C15 C16 119.2(2) . . ?
C15 C16 C11 121.2(2) . . ?
O1 C17 C18 122.7(2) . . ?
C22 C17 O1 115.58(19) . . ?
C22 C17 C18 121.5(2) . . ?
C17 C18 C19 118.5(2) . . ?
C20 C19 C18 120.6(2) . . ?
C19 C20 C21 119.7(2) . . ?
C22 C21 C20 120.6(2) . . ?
C17 C22 C21 119.1(2) . . ?
C24 C23 C29 120.1(2) . . ?
C28 C23 C24 118.4(2) . . ?
C28 C23 C29 121.4(2) . . ?
C25 C24 C23 121.0(2) . . ?
C26 C25 C24 118.2(2) . . ?
F2 C26 C25 118.3(2) . . ?
F2 C26 C27 118.8(2) . . ?
C27 C26 C25 122.9(2) . . ?
C26 C27 C28 118.4(2) . . ?
C27 C28 C23 121.0(2) . . ?
N3 C29 C23 116.5(2) . . ?
N3 C29 C30 124.0(2) . . ?
C23 C29 C30 119.5(2) . . ?
N4 C31 C32 124.2(2) . . ?
N4 C31 C33 115.8(2) . . ?
C33 C31 C32 119.94(19) . . ?
C34 C33 C31 121.5(2) . . ?
C34 C33 C38 118.1(2) . . ?
C38 C33 C31 120.4(2) . . ?
C35 C34 C33 121.4(2) . . ?
C36 C35 C34 118.9(2) . . ?
O2 C36 C35 123.7(2) . . ?
O2 C36 C37 115.15(19) . . ?
C35 C36 C37 120.9(2) . . ?
C38 C37 C36 119.4(2) . . ?
C37 C38 C33 121.3(2) . . ?
C40 C39 O2 122.9(2) . . ?
C44 C39 O2 115.3(2) . . ?
C44 C39 C40 121.5(2) . . ?
C41 C40 C39 118.8(2) . . ?
C40 C41 C42 120.4(2) . . ?
C43 C42 C41 119.9(2) . . ?
C42 C43 C44 120.5(2) . . ?
C39 C44 C43 118.8(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
