# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_mo_HR070220_0m
_database_code_depnum_ccdc_archive 'CCDC 2003103'
_audit_update_record             
;
2020-05-10 deposited with the CCDC.	2022-07-25 downloaded from the CCDC.
;
_audit_creation_date             2020-02-10
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6020)
;
_chemical_name_systematic        DPM
_chemical_formula_moiety         'C27 H19 F4 N3'
_chemical_formula_sum            'C27 H19 F4 N3'
_chemical_formula_weight         461.466
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
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'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'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'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 0.277599990368
'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 -11.5290002823
'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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_symmetry_cell_setting           Monoclinic'
_symmetry_space_group_name_H-M   P2(1)/n
_cell_length_a                   9.2264(8)
_cell_length_b                   12.9652(11)
_cell_length_c                   18.7337(18)
_cell_angle_alpha                90
_cell_angle_beta                 99.768(3)
_cell_angle_gamma                90
_cell_volume                     2208.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    115(2)
_cell_measurement_reflns_used    3464
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      26.86
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       prism
_exptl_crystal_F_000             952.572
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0994
_diffrn_reflns_av_unetI/netI     0.0917
_diffrn_reflns_Laue_measured_fraction_full 0.9970
_diffrn_reflns_Laue_measured_fraction_max 0.9961
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22530
_diffrn_reflns_point_group_measured_fraction_full 0.9970
_diffrn_reflns_point_group_measured_fraction_max 0.9961
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         2.21
_diffrn_ambient_temperature      115.3
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9970
_diffrn_measured_fraction_theta_max 0.9961
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -11
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              -9
_reflns_number_gt                2982
_reflns_number_total             4849
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.4771
_refine_diff_density_min         -0.6358
_refine_diff_density_rms         0.1259
_refine_ls_d_res_high            0.7801
_refine_ls_d_res_low             9.2311
_refine_ls_goodness_of_fit_ref   1.0465
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4849
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1180
_refine_ls_R_factor_gt           0.0607
_refine_ls_restrained_S_all      1.0465
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0361P)²+1.7267P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1178
_refine_ls_wR_factor_ref         0.1442
_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:
 C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C9(H9), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16),
 C20(H20), C21(H21), C22(H22), C25(H25), C26(H26), C27(H27), N2(H2a)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c)
;
_atom_sites_solution_primary     iterative
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
C1 C -0.2502(3) 0.3872(2) 0.48277(16) 0.0284(7) Uani 1.000000 .
H1a H -0.3162(12) 0.4433(4) 0.4867(8) 0.0426(10) Uiso 1.000000 GR
H1b H -0.3042(13) 0.3302(9) 0.4587(5) 0.0426(10) Uiso 1.000000 GR
H1c H -0.2035(3) 0.3663(13) 0.5303(4) 0.0426(10) Uiso 1.000000 GR
C2 C -0.1523(3) 0.50326(19) 0.39653(14) 0.0221(6) Uani 1.000000 .
H2 H -0.2325(3) 0.54775(19) 0.38842(14) 0.0265(7) Uiso 1.000000 R
C4 C 0.0649(3) 0.42636(19) 0.39315(14) 0.0223(6) Uani 1.000000 .
H4 H 0.1569(3) 0.41126(19) 0.38179(14) 0.0267(7) Uiso 1.000000 R
C5 C -0.0044(3) 0.37197(18) 0.43916(14) 0.0208(6) Uani 1.000000 .
C6 C 0.0427(3) 0.27740(18) 0.48424(15) 0.0204(6) Uani 1.000000 .
H6 H 0.0386(3) 0.29560(18) 0.53463(15) 0.0245(7) Uiso 1.000000 R
C7 C -0.0597(3) 0.18525(18) 0.46532(15) 0.0219(6) Uani 1.000000 .
C8 C -0.1061(3) 0.1257(2) 0.51882(16) 0.0282(7) Uani 1.000000 .
C9 C -0.1993(3) 0.0431(2) 0.50505(19) 0.0362(8) Uani 1.000000 .
H9 H -0.2280(3) 0.0060(2) 0.54281(19) 0.0434(9) Uiso 1.000000 R
C10 C -0.2496(3) 0.0161(2) 0.43404(19) 0.0385(8) Uani 1.000000 .
H10 H -0.3126(3) -0.0399(2) 0.42375(19) 0.0462(10) Uiso 1.000000 R
C11 C -0.2077(3) 0.0709(2) 0.37841(18) 0.0329(7) Uani 1.000000 .
H11 H -0.2419(3) 0.0534(2) 0.33035(18) 0.0395(9) Uiso 1.000000 R
C12 C -0.1132(3) 0.1528(2) 0.39614(16) 0.0270(6) Uani 1.000000 .
C13 C 0.2000(3) 0.24863(19) 0.48137(15) 0.0214(6) Uani 1.000000 .
C14 C 0.2681(3) 0.2113(2) 0.42751(16) 0.0276(6) Uani 1.000000 .
H14 H 0.2239(3) 0.1984(2) 0.37994(16) 0.0331(8) Uiso 1.000000 R
C15 C 0.4193(3) 0.1957(2) 0.45743(17) 0.0321(7) Uani 1.000000 .
H15 H 0.4919(3) 0.1704(2) 0.43321(17) 0.0386(8) Uiso 1.000000 R
C16 C 0.4370(3) 0.2247(2) 0.52817(18) 0.0344(7) Uani 1.000000 .
H16 H 0.5247(3) 0.2227(2) 0.56105(18) 0.0412(9) Uiso 1.000000 R
C17 C 0.0076(3) 0.58622(19) 0.31361(14) 0.0212(6) Uani 1.000000 .
C18 C 0.1442(3) 0.56492(19) 0.28283(15) 0.0224(6) Uani 1.000000 .
C19 C 0.1545(3) 0.4847(2) 0.23525(16) 0.0300(7) Uani 1.000000 .
C20 C 0.2796(3) 0.4604(2) 0.20872(18) 0.0390(8) Uani 1.000000 .
H20 H 0.2815(3) 0.4043(2) 0.17797(18) 0.0468(9) Uiso 1.000000 R
C21 C 0.4028(3) 0.5210(2) 0.22853(18) 0.0393(8) Uani 1.000000 .
H21 H 0.4882(3) 0.5065(2) 0.21028(18) 0.0472(10) Uiso 1.000000 R
C22 C 0.4001(3) 0.6033(2) 0.27541(18) 0.0375(8) Uani 1.000000 .
H22 H 0.4831(3) 0.6440(2) 0.28940(18) 0.0450(9) Uiso 1.000000 R
C23 C 0.2714(3) 0.6232(2) 0.30077(15) 0.0262(6) Uani 1.000000 .
C24 C -0.0700(3) 0.67316(19) 0.29052(15) 0.0238(6) Uani 1.000000 .
C25 C -0.0400(3) 0.7446(2) 0.23553(15) 0.0284(7) Uani 1.000000 .
H25 H 0.0374(3) 0.7411(2) 0.20961(15) 0.0341(8) Uiso 1.000000 R
C26 C -0.2375(3) 0.7908(2) 0.28089(16) 0.0341(7) Uani 1.000000 .
H26 H -0.3184(3) 0.8298(2) 0.28808(16) 0.0410(9) Uiso 1.000000 R
C27 C -0.1463(3) 0.8176(2) 0.22912(17) 0.0350(7) Uani 1.000000 .
H27 H -0.1577(3) 0.8735(2) 0.19759(17) 0.0420(9) Uiso 1.000000 R
C28 C -0.0272(3) 0.51107(19) 0.36489(14) 0.0216(6) Uani 1.000000 .
F1 F -0.05655(19) 0.15207(13) 0.58860(9) 0.0420(5) Uani 1.000000 .
F2 F -0.06575(19) 0.20368(13) 0.34053(9) 0.0419(5) Uani 1.000000 .
F3 F 0.03268(19) 0.42633(13) 0.21464(10) 0.0440(5) Uani 1.000000 .
F4 F 0.26818(17) 0.70351(12) 0.34722(9) 0.0358(4) Uani 1.000000 .
N1 N -0.1387(2) 0.42030(15) 0.44115(12) 0.0211(5) Uani 1.000000 .
N2 N 0.3039(2) 0.25739(17) 0.54280(13) 0.0292(6) Uani 1.000000 .
H2a H 0.2879(2) 0.27984(17) 0.58397(13) 0.0351(7) Uiso 1.000000 R
N3 N -0.1967(2) 0.70603(16) 0.31743(13) 0.0270(5) Uani 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1a 0.9600 . ?
C1 H1b 0.9600 . ?
C1 H1c 0.9600 . ?
C1 N1 1.456(3) . ?
C2 H2 0.9300 . ?
C2 C28 1.388(4) . ?
C2 N1 1.355(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.355(4) . ?
C4 C28 1.434(3) . ?
C5 C6 1.510(3) . ?
C5 N1 1.395(3) . ?
C6 H6 0.9800 . ?
C6 C7 1.527(3) . ?
C6 C13 1.508(3) . ?
C7 C8 1.389(4) . ?
C7 C12 1.372(4) . ?
C8 C9 1.371(4) . ?
C8 F1 1.353(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.377(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.369(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.379(4) . ?
C12 F2 1.366(3) . ?
C13 C14 1.364(4) . ?
C13 N2 1.371(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.427(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.361(4) . ?
C16 H16 0.9300 . ?
C16 N2 1.370(4) . ?
C17 C18 1.498(4) . ?
C17 C24 1.366(3) . ?
C17 C28 1.442(4) . ?
C18 C19 1.384(4) . ?
C18 C23 1.388(4) . ?
C19 C20 1.369(4) . ?
C19 F3 1.355(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.380(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.385(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.376(4) . ?
C23 F4 1.361(3) . ?
C24 C25 1.447(4) . ?
C24 N3 1.415(3) . ?
C25 H25 0.9300 . ?
C25 C27 1.354(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.430(4) . ?
C26 N3 1.316(3) . ?
C27 H27 0.9300 . ?
N2 H2a 0.8600 . ?

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
H1b C1 H1a 109.5 . . ?
H1c C1 H1a 109.5 . . ?
H1c C1 H1b 109.5 . . ?
N1 C1 H1a 109.5 . . ?
N1 C1 H1b 109.5 . . ?
N1 C1 H1c 109.5 . . ?
C28 C2 H2 125.53(14) . . ?
N1 C2 H2 125.53(14) . . ?
N1 C2 C28 108.9(2) . . ?
C5 C4 H4 125.69(15) . . ?
C28 C4 H4 125.69(15) . . ?
C28 C4 C5 108.6(2) . . ?
C6 C5 C4 131.0(2) . . ?
N1 C5 C4 107.5(2) . . ?
N1 C5 C6 121.5(2) . . ?
H6 C6 C5 106.77(14) . . ?
C7 C6 C5 113.4(2) . . ?
C7 C6 H6 106.77(15) . . ?
C13 C6 C5 111.6(2) . . ?
C13 C6 H6 106.77(15) . . ?
C13 C6 C7 111.1(2) . . ?
C8 C7 C6 121.4(2) . . ?
C12 C7 C6 124.6(2) . . ?
C12 C7 C8 113.9(2) . . ?
C9 C8 C7 124.0(3) . . ?
F1 C8 C7 117.5(2) . . ?
F1 C8 C9 118.5(3) . . ?
H9 C9 C8 120.74(19) . . ?
C10 C9 C8 118.5(3) . . ?
C10 C9 H9 120.74(17) . . ?
H10 C10 C9 119.62(17) . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10 119.62(18) . . ?
H11 C11 C10 121.17(18) . . ?
C12 C11 C10 117.7(3) . . ?
C12 C11 H11 121.17(18) . . ?
C11 C12 C7 125.1(3) . . ?
F2 C12 C7 117.5(2) . . ?
F2 C12 C11 117.4(3) . . ?
C14 C13 C6 132.9(2) . . ?
N2 C13 C6 119.3(2) . . ?
N2 C13 C14 107.9(2) . . ?
H14 C14 C13 126.22(15) . . ?
C15 C14 C13 107.6(3) . . ?
C15 C14 H14 126.22(18) . . ?
H15 C15 C14 126.54(18) . . ?
C16 C15 C14 106.9(3) . . ?
C16 C15 H15 126.54(17) . . ?
H16 C16 C15 125.76(17) . . ?
N2 C16 C15 108.5(2) . . ?
N2 C16 H16 125.76(17) . . ?
C24 C17 C18 117.4(2) . . ?
C28 C17 C18 115.4(2) . . ?
C28 C17 C24 127.2(2) . . ?
C19 C18 C17 122.7(2) . . ?
C23 C18 C17 122.6(2) . . ?
C23 C18 C19 114.7(3) . . ?
C20 C19 C18 124.1(3) . . ?
F3 C19 C18 117.3(2) . . ?
F3 C19 C20 118.6(3) . . ?
H20 C20 C19 120.69(18) . . ?
C21 C20 C19 118.6(3) . . ?
C21 C20 H20 120.69(19) . . ?
H21 C21 C20 119.79(19) . . ?
C22 C21 C20 120.4(3) . . ?
C22 C21 H21 119.79(17) . . ?
H22 C22 C21 120.89(17) . . ?
C23 C22 C21 118.2(3) . . ?
C23 C22 H22 120.89(17) . . ?
C22 C23 C18 123.9(3) . . ?
F4 C23 C18 117.5(2) . . ?
F4 C23 C22 118.5(2) . . ?
C25 C24 C17 126.9(3) . . ?
N3 C24 C17 123.8(2) . . ?
N3 C24 C25 109.3(2) . . ?
H25 C25 C24 126.65(16) . . ?
C27 C25 C24 106.7(3) . . ?
C27 C25 H25 126.65(19) . . ?
C27 C26 H26 123.01(16) . . ?
N3 C26 H26 123.01(17) . . ?
N3 C26 C27 114.0(3) . . ?
C26 C27 C25 105.7(3) . . ?
H27 C27 C25 127.14(19) . . ?
H27 C27 C26 127.14(16) . . ?
C4 C28 C2 105.7(2) . . ?
C17 C28 C2 129.0(2) . . ?
C17 C28 C4 125.3(2) . . ?
C2 N1 C1 124.3(2) . . ?
C5 N1 C1 126.4(2) . . ?
C5 N1 C2 109.3(2) . . ?
C16 N2 C13 109.2(2) . . ?
H2a N2 C13 125.40(15) . . ?
H2a N2 C16 125.40(17) . . ?
C26 N3 C24 104.3(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
C1 N1 C2 C28 -179.0(3) . . . . ?
C1 N1 C5 C4 179.0(3) . . . . ?
C1 N1 C5 C6 -2.0(3) . . . . ?
C2 C28 C4 C5 0.0(2) . . . . ?
C2 C28 C17 C18 -172.5(3) . . . . ?
C2 C28 C17 C24 7.3(3) . . . . ?
C2 N1 C5 C4 0.3(2) . . . . ?
C2 N1 C5 C6 179.30(19) . . . . ?
C4 C5 C6 C7 -119.3(3) . . . . ?
C4 C5 C6 C13 7.1(3) . . . . ?
C4 C28 C17 C18 6.8(3) . . . . ?
C4 C28 C17 C24 -173.4(2) . . . . ?
C5 C6 C7 C8 -134.9(2) . . . . ?
C5 C6 C7 C12 45.6(3) . . . . ?
C5 C6 C13 C14 -68.4(3) . . . . ?
C5 C6 C13 N2 112.9(2) . . . . ?
C6 C7 C8 C9 179.1(2) . . . . ?
C6 C7 C8 F1 -0.3(3) . . . . ?
C6 C7 C12 C11 -178.8(2) . . . . ?
C6 C7 C12 F2 3.2(3) . . . . ?
C6 C13 C14 C15 -178.2(3) . . . . ?
C6 C13 N2 C16 178.4(2) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C7 C12 C11 C10 -1.4(3) . . . . ?
C8 C9 C10 C11 -0.2(3) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
C10 C11 C12 F2 176.6(2) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C13 N2 C16 C15 0.4(2) . . . . ?
C14 C15 C16 N2 -0.0(2) . . . . ?
C17 C18 C19 C20 -177.0(3) . . . . ?
C17 C18 C19 F3 2.3(3) . . . . ?
C17 C18 C23 C22 177.6(3) . . . . ?
C17 C18 C23 F4 -1.2(3) . . . . ?
C17 C24 C25 C27 178.6(3) . . . . ?
C17 C24 N3 C26 -179.4(3) . . . . ?
C18 C19 C20 C21 -2.0(3) . . . . ?
C18 C23 C22 C21 0.8(3) . . . . ?
C19 C20 C21 C22 1.2(4) . . . . ?
C20 C21 C22 C23 -0.7(4) . . . . ?
C21 C22 C23 F4 179.6(3) . . . . ?
C24 C25 C27 C26 1.0(2) . . . . ?
C24 N3 C26 C27 0.8(2) . . . . ?
C25 C27 C26 N3 -1.2(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_mo_hr200120_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2003102'
_audit_update_record             
;
2021-05-11 deposited with the CCDC.	2022-07-25 downloaded from the CCDC.
;
_audit_creation_date             2021-05-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H19 F4 N3 O'
_chemical_formula_sum            'C27 H19 F4 N3 O'
_chemical_formula_weight         477.45
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.346(2)
_cell_length_b                   12.355(4)
_cell_length_c                   20.062(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.210(9)
_cell_angle_gamma                90
_cell_volume                     2255.2(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2954
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.88
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1154 before and 0.0723 after correction. The Ratio of minimum to maximum transmission is 0.8195. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1472
_diffrn_reflns_av_unetI/netI     0.1221
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            19168
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.243
_diffrn_ambient_temperature      120.24
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2493
_reflns_number_total             3959
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       0.0073(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         3959
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1528
_refine_ls_R_factor_gt           0.0960
_refine_ls_restrained_S_all      1.107
_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)+(0.0656P)²+6.4302P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1972
_refine_ls_wR_factor_ref         0.2184
_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:
 C00A(H00A)
2.b Aromatic/amide H refined with riding coordinates:
 N007(H007), N008(H008), C00K(H00K), C00L(H00L), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00W(H00W),
 C00X(H00X), C00Y(H00Y), C00Z(H00Z)
2.c Idealised Me refined as rotating group:
 C00V(H00B,H00C,H00D)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F001 F 0.5366(3) 0.1728(2) 0.65566(15) 0.0264(8) Uani 1 1 d . . . . .
F002 F 0.5517(4) 0.1872(3) 0.42337(16) 0.0326(9) Uani 1 1 d . . . . .
F003 F 0.5116(3) 0.4147(3) 0.80871(17) 0.0347(9) Uani 1 1 d . . . . .
F004 F 0.1979(4) 0.6530(3) 0.66219(18) 0.0388(9) Uani 1 1 d . . . . .
O005 O 0.7405(4) 0.5798(3) 0.62509(18) 0.0225(9) Uani 1 1 d . . . . .
N006 N 0.6102(4) 0.4338(3) 0.5698(2) 0.0178(10) Uani 1 1 d . . . . .
N007 N 0.1630(4) 0.2813(4) 0.4735(2) 0.0210(10) Uani 1 1 d . . . . .
H007 H 0.173217 0.320466 0.438212 0.025 Uiso 1 1 calc R . . . .
N008 N 0.6795(5) 0.7144(4) 0.7198(2) 0.0230(11) Uani 1 1 d . . . . .
H008 H 0.723022 0.691188 0.687937 0.028 Uiso 1 1 calc R . . . .
C009 C 0.6341(5) 0.5153(4) 0.6172(3) 0.0155(11) Uani 1 1 d . . . . .
C00A C 0.4322(5) 0.2808(4) 0.5260(3) 0.0167(11) Uani 1 1 d . . . . .
H00A H 0.430687 0.307957 0.478896 0.020 Uiso 1 1 calc R . . . .
C00B C 0.2761(5) 0.2488(4) 0.5263(3) 0.0183(12) Uani 1 1 d . . . . .
C00C C 0.4870(5) 0.5719(4) 0.7055(3) 0.0166(11) Uani 1 1 d . . . . .
C00D C 0.5372(5) 0.1853(4) 0.5385(3) 0.0179(12) Uani 1 1 d . . . . .
C00E C 0.5872(5) 0.1370(4) 0.6017(3) 0.0197(12) Uani 1 1 d . . . . .
C00F C 0.4837(5) 0.3742(4) 0.5746(3) 0.0180(12) Uani 1 1 d . . . . .
C00G C 0.5592(5) 0.6668(4) 0.7370(3) 0.0195(12) Uani 1 1 d . . . . .
C00H C 0.5149(5) 0.5082(4) 0.6539(3) 0.0180(12) Uani 1 1 d . . . . .
C00I C 0.3606(6) 0.5368(4) 0.7352(3) 0.0174(12) Uani 1 1 d . . . . .
C00J C 0.2202(6) 0.5773(4) 0.7133(3) 0.0220(12) Uani 1 1 d . . . . .
C00K C 0.6837(6) 0.0489(4) 0.6129(3) 0.0254(13) Uani 1 1 d . . . . .
H00K H 0.714061 0.017392 0.657018 0.030 Uiso 1 1 calc R . . . .
C00L C 0.4265(5) 0.4167(4) 0.6239(3) 0.0169(11) Uani 1 1 d . . . . .
H00L H 0.341354 0.390905 0.637251 0.020 Uiso 1 1 calc R . . . .
C00M C 0.3764(6) 0.4603(4) 0.7867(3) 0.0217(12) Uani 1 1 d . . . . .
C00N C 0.6876(5) 0.0553(4) 0.4942(3) 0.0249(13) Uani 1 1 d . . . . .
H00N H 0.720702 0.027643 0.456153 0.030 Uiso 1 1 calc R . . . .
C00O C 0.2641(6) 0.4254(4) 0.8148(3) 0.0248(13) Uani 1 1 d . . . . .
H00O H 0.279908 0.371226 0.849316 0.030 Uiso 1 1 calc R . . . .
C00P C 0.0615(6) 0.1873(5) 0.5427(3) 0.0256(13) Uani 1 1 d . . . . .
H00P H -0.008924 0.151760 0.562502 0.031 Uiso 1 1 calc R . . . .
C00Q C 0.7336(6) 0.0091(4) 0.5582(3) 0.0264(14) Uani 1 1 d . . . . .
H00Q H 0.799834 -0.050341 0.564522 0.032 Uiso 1 1 calc R . . . .
C00R C 0.5250(6) 0.7299(5) 0.7884(3) 0.0250(13) Uani 1 1 d . . . . .
H00R H 0.446420 0.717892 0.810324 0.030 Uiso 1 1 calc R . . . .
C00S C 0.7199(6) 0.8035(4) 0.7602(3) 0.0267(13) Uani 1 1 d . . . . .
H00S H 0.800231 0.850061 0.759064 0.032 Uiso 1 1 calc R . . . .
C00T C 0.2140(6) 0.1902(4) 0.5697(3) 0.0232(13) Uani 1 1 d . . . . .
H00T H 0.264868 0.157035 0.611080 0.028 Uiso 1 1 calc R . . . .
C00U C 0.5931(6) 0.1420(5) 0.4864(3) 0.0243(13) Uani 1 1 d . . . . .
C00V C 0.7082(6) 0.4108(4) 0.5247(3) 0.0246(13) Uani 1 1 d . . . . .
H00B H 0.775893 0.471675 0.525673 0.037 Uiso 1 1 calc GR . . . .
H00C H 0.650259 0.400299 0.477880 0.037 Uiso 1 1 calc GR . . . .
H00D H 0.764546 0.344972 0.540204 0.037 Uiso 1 1 calc GR . . . .
C00W C 0.6262(6) 0.8138(4) 0.8020(3) 0.0247(13) Uani 1 1 d . . . . .
H00W H 0.629031 0.869208 0.835115 0.030 Uiso 1 1 calc R . . . .
C00X C 0.1268(6) 0.4715(5) 0.7914(3) 0.0276(14) Uani 1 1 d . . . . .
H00X H 0.047708 0.450420 0.811035 0.033 Uiso 1 1 calc R . . . .
C00Y C 0.0331(6) 0.2439(5) 0.4837(3) 0.0275(14) Uani 1 1 d . . . . .
H00Y H -0.061076 0.255571 0.454563 0.033 Uiso 1 1 calc R . . . .
C00Z C 0.1036(6) 0.5477(5) 0.7400(3) 0.0290(14) Uani 1 1 d . . . . .
H00Z H 0.009272 0.578852 0.723418 0.035 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
F001 C00E 1.351(6) . ?
F002 C00U 1.355(6) . ?
F003 C00M 1.361(6) . ?
F004 C00J 1.368(6) . ?
O005 C009 1.256(6) . ?
N006 C009 1.367(6) . ?
N006 C00F 1.415(6) . ?
N006 C00V 1.455(6) . ?
N007 H007 0.8800 . ?
N007 C00B 1.375(6) . ?
N007 C00Y 1.358(7) . ?
N008 H008 0.8800 . ?
N008 C00G 1.381(6) . ?
N008 C00S 1.369(7) . ?
C009 C00H 1.472(7) . ?
C00A H00A 1.0000 . ?
C00A C00B 1.513(7) . ?
C00A C00D 1.518(7) . ?
C00A C00F 1.517(7) . ?
C00B C00T 1.361(7) . ?
C00C C00G 1.426(7) . ?
C00C C00H 1.372(7) . ?
C00C C00I 1.504(7) . ?
C00D C00E 1.383(7) . ?
C00D C00U 1.378(7) . ?
C00E C00K 1.398(7) . ?
C00F C00L 1.335(7) . ?
C00G C00R 1.387(8) . ?
C00H C00L 1.448(7) . ?
C00I C00J 1.379(7) . ?
C00I C00M 1.382(7) . ?
C00J C00Z 1.369(7) . ?
C00K H00K 0.9500 . ?
C00K C00Q 1.377(8) . ?
C00L H00L 0.9500 . ?
C00M C00O 1.370(7) . ?
C00N H00N 0.9500 . ?
C00N C00Q 1.381(8) . ?
C00N C00U 1.375(8) . ?
C00O H00O 0.9500 . ?
C00O C00X 1.384(8) . ?
C00P H00P 0.9500 . ?
C00P C00T 1.404(7) . ?
C00P C00Y 1.348(8) . ?
C00Q H00Q 0.9500 . ?
C00R H00R 0.9500 . ?
C00R C00W 1.388(8) . ?
C00S H00S 0.9500 . ?
C00S C00W 1.350(8) . ?
C00T H00T 0.9500 . ?
C00V H00B 0.9800 . ?
C00V H00C 0.9800 . ?
C00V H00D 0.9800 . ?
C00W H00W 0.9500 . ?
C00X H00X 0.9500 . ?
C00X C00Z 1.376(8) . ?
C00Y H00Y 0.9500 . ?
C00Z H00Z 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
C009 N006 C00F 110.0(4) . . ?
C009 N006 C00V 123.3(4) . . ?
C00F N006 C00V 126.6(4) . . ?
C00B N007 H007 125.1 . . ?
C00Y N007 H007 125.1 . . ?
C00Y N007 C00B 109.9(4) . . ?
C00G N008 H008 125.5 . . ?
C00S N008 H008 125.5 . . ?
C00S N008 C00G 108.9(5) . . ?
O005 C009 N006 123.7(4) . . ?
O005 C009 C00H 129.9(5) . . ?
N006 C009 C00H 106.4(4) . . ?
C00B C00A H00A 106.6 . . ?
C00B C00A C00D 112.6(4) . . ?
C00B C00A C00F 111.1(4) . . ?
C00D C00A H00A 106.6 . . ?
C00F C00A H00A 106.6 . . ?
C00F C00A C00D 112.8(4) . . ?
N007 C00B C00A 119.5(4) . . ?
C00T C00B N007 106.5(4) . . ?
C00T C00B C00A 134.0(5) . . ?
C00G C00C C00I 113.4(4) . . ?
C00H C00C C00G 130.8(5) . . ?
C00H C00C C00I 115.9(4) . . ?
C00E C00D C00A 123.8(5) . . ?
C00U C00D C00A 121.3(5) . . ?
C00U C00D C00E 114.9(5) . . ?
F001 C00E C00D 119.1(5) . . ?
F001 C00E C00K 117.2(5) . . ?
C00D C00E C00K 123.6(5) . . ?
N006 C00F C00A 120.0(4) . . ?
C00L C00F N006 109.2(5) . . ?
C00L C00F C00A 130.8(5) . . ?
N008 C00G C00C 124.7(5) . . ?
N008 C00G C00R 106.6(5) . . ?
C00R C00G C00C 128.7(5) . . ?
C00C C00H C009 129.8(5) . . ?
C00C C00H C00L 124.9(4) . . ?
C00L C00H C009 105.3(4) . . ?
C00J C00I C00C 123.0(5) . . ?
C00J C00I C00M 114.7(5) . . ?
C00M C00I C00C 122.2(5) . . ?
F004 C00J C00I 117.3(4) . . ?
F004 C00J C00Z 118.5(5) . . ?
C00Z C00J C00I 124.2(5) . . ?
C00E C00K H00K 120.8 . . ?
C00Q C00K C00E 118.3(5) . . ?
C00Q C00K H00K 120.8 . . ?
C00F C00L C00H 109.1(4) . . ?
C00F C00L H00L 125.4 . . ?
C00H C00L H00L 125.4 . . ?
F003 C00M C00I 117.3(4) . . ?
F003 C00M C00O 118.5(5) . . ?
C00O C00M C00I 124.1(5) . . ?
C00Q C00N H00N 120.6 . . ?
C00U C00N H00N 120.6 . . ?
C00U C00N C00Q 118.9(5) . . ?
C00M C00O H00O 121.0 . . ?
C00M C00O C00X 118.0(5) . . ?
C00X C00O H00O 121.0 . . ?
C00T C00P H00P 126.1 . . ?
C00Y C00P H00P 126.1 . . ?
C00Y C00P C00T 107.7(5) . . ?
C00K C00Q C00N 120.2(5) . . ?
C00K C00Q H00Q 119.9 . . ?
C00N C00Q H00Q 119.9 . . ?
C00G C00R H00R 126.2 . . ?
C00G C00R C00W 107.7(5) . . ?
C00W C00R H00R 126.2 . . ?
N008 C00S H00S 125.9 . . ?
C00W C00S N008 108.3(5) . . ?
C00W C00S H00S 125.9 . . ?
C00B C00T C00P 108.1(5) . . ?
C00B C00T H00T 125.9 . . ?
C00P C00T H00T 125.9 . . ?
F002 C00U C00D 118.1(5) . . ?
F002 C00U C00N 117.8(5) . . ?
C00N C00U C00D 124.2(5) . . ?
N006 C00V H00B 109.5 . . ?
N006 C00V H00C 109.5 . . ?
N006 C00V H00D 109.5 . . ?
H00B C00V H00C 109.5 . . ?
H00B C00V H00D 109.5 . . ?
H00C C00V H00D 109.5 . . ?
C00R C00W H00W 125.8 . . ?
C00S C00W C00R 108.5(5) . . ?
C00S C00W H00W 125.8 . . ?
C00O C00X H00X 119.7 . . ?
C00Z C00X C00O 120.7(5) . . ?
C00Z C00X H00X 119.7 . . ?
N007 C00Y H00Y 126.1 . . ?
C00P C00Y N007 107.8(5) . . ?
C00P C00Y H00Y 126.1 . . ?
C00J C00Z C00X 118.2(5) . . ?
C00J C00Z H00Z 120.9 . . ?
C00X C00Z H00Z 120.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
