# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_lsyichun_0m
_audit_block_doi                 10.5517/ccdc.csd.cc259y2j
_database_code_depnum_ccdc_archive 'CCDC 2005547'
loop_
_audit_author_name
_audit_author_address
'Kailin Xu'
;Guangdong University of Technology
China
;
_audit_update_record             
;
2020-09-12 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;
_audit_creation_date             2020-09-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 F N5 O2, C2 H6 O'
_chemical_formula_sum            'C20 H26 F N5 O3'
_chemical_formula_weight         403.46
_chemical_absolute_configuration rmad
_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'
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'
H H 0.0000 0.0000 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.1053(2)
_cell_length_b                   7.9388(3)
_cell_length_c                   18.2289(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.7230(10)
_cell_angle_gamma                90
_cell_volume                     1021.18(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9993
_cell_measurement_temperature    240(2)
_cell_measurement_theta_max      72.04
_cell_measurement_theta_min      7.49
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.801
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1470 before and 0.0871 after correction.
The Ratio of minimum to maximum transmission is 0.8585.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18454
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.144
_diffrn_reflns_theta_min         7.494
_diffrn_ambient_temperature      240.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.812
_reflns_Friedel_fraction_full    0.940
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                3665
_reflns_number_total             3852
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (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         0.185
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3852
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0458P)²+0.2231P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0908
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9(2)
 0.1(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Ternary CH refined with riding coordinates:
 C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C1(H1C,H1D), C11(H11A,H11B), C3(H3A,H3B), C5(H5A,H5B), C4(H4A,H4B), C19(H19A,
 H19B)
3.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C7(H7), C16(H16), C15(H15)
3.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C20(H20A,H20B,H20C)
3.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.2821(2) -0.1013(2) 0.50678(9) 0.0554(4) Uani 1 1 d . . . . .
O2 O 0.4642(3) -0.0202(3) 0.62840(10) 0.0497(5) Uani 1 1 d . . . . .
O1 O 0.3329(3) -0.3980(2) 0.80144(12) 0.0527(5) Uani 1 1 d . . . . .
N2 N 0.0090(3) 0.1327(2) 0.77755(10) 0.0330(4) Uani 1 1 d . . . . .
N1 N 0.0385(3) 0.5068(3) 0.90660(12) 0.0413(5) Uani 1 1 d . . . . .
N5 N 0.0396(4) 0.6387(3) 0.63838(15) 0.0579(6) Uani 1 1 d . . . . .
N4 N 0.2463(2) 0.0542(2) 0.70468(10) 0.0296(4) Uani 1 1 d . . . . .
N3 N 0.4111(3) -0.2027(2) 0.71968(11) 0.0340(4) Uani 1 1 d . . . . .
C1 C 0.0909(3) 0.2476(3) 0.83693(12) 0.0331(5) Uani 1 1 d . . . . .
H1C H 0.213847 0.289173 0.825244 0.040 Uiso 1 1 calc R . . . .
H1D H 0.111912 0.185590 0.883650 0.040 Uiso 1 1 calc R . . . .
C6 C 0.1397(3) 0.0095(3) 0.76099(11) 0.0303(4) Uani 1 1 d . . . . .
C9 C 0.3793(3) -0.0544(3) 0.68042(12) 0.0328(5) Uani 1 1 d . . . . .
C13 C -0.0520(3) 0.0477(3) 0.58328(13) 0.0353(5) Uani 1 1 d . . . . .
H13 H 0.010372 -0.054010 0.596863 0.042 Uiso 1 1 calc R . . . .
C7 C 0.1647(3) -0.1409(3) 0.79418(13) 0.0378(5) Uani 1 1 d . . . . .
H7 H 0.090014 -0.169946 0.831538 0.045 Uiso 1 1 calc R . . . .
C11 C 0.2041(3) 0.2090(3) 0.66237(12) 0.0327(4) Uani 1 1 d . . . . .
H11A H 0.307722 0.231741 0.632677 0.039 Uiso 1 1 calc R . . . .
H11B H 0.198095 0.303209 0.696775 0.039 Uiso 1 1 calc R . . . .
C2 C -0.0400(3) 0.3964(3) 0.84558(13) 0.0353(5) Uani 1 1 d . . . . .
H2 H -0.052060 0.462544 0.799235 0.042 Uiso 1 1 calc R . . . .
C12 C 0.0195(3) 0.2003(3) 0.61176(11) 0.0295(4) Uani 1 1 d . . . . .
C17 C -0.0788(3) 0.3476(3) 0.58972(12) 0.0336(5) Uani 1 1 d . . . . .
C8 C 0.3030(3) -0.2583(3) 0.77390(13) 0.0369(5) Uani 1 1 d . . . . .
C18 C -0.0117(3) 0.5088(3) 0.61724(13) 0.0398(5) Uani 1 1 d . . . . .
C14 C -0.2163(3) 0.0484(3) 0.53468(13) 0.0398(5) Uani 1 1 d . . . . .
C16 C -0.2444(3) 0.3424(3) 0.54027(14) 0.0428(6) Uani 1 1 d . . . . .
H16 H -0.308608 0.442918 0.526112 0.051 Uiso 1 1 calc R . . . .
C15 C -0.3138(3) 0.1919(4) 0.51231(14) 0.0452(6) Uani 1 1 d . . . . .
H15 H -0.424781 0.187080 0.478818 0.054 Uiso 1 1 calc R . . . .
C3 C -0.2351(4) 0.3338(4) 0.85838(16) 0.0473(6) Uani 1 1 d . . . . .
H3A H -0.228080 0.279805 0.906973 0.057 Uiso 1 1 calc R . . . .
H3B H -0.322017 0.429671 0.858136 0.057 Uiso 1 1 calc R . . . .
C5 C -0.1735(3) 0.0640(3) 0.79426(18) 0.0478(6) Uani 1 1 d . . . . .
H5A H -0.156091 0.002331 0.841139 0.057 Uiso 1 1 calc R . . . .
H5B H -0.223972 -0.014271 0.755243 0.057 Uiso 1 1 calc R . . . .
C4 C -0.3113(4) 0.2090(4) 0.79938(19) 0.0554(7) Uani 1 1 d . . . . .
H4A H -0.332922 0.266496 0.751564 0.066 Uiso 1 1 calc R . . . .
H4B H -0.433132 0.164697 0.811016 0.066 Uiso 1 1 calc R . . . .
C10 C 0.5525(4) -0.3190(4) 0.69615(17) 0.0484(6) Uani 1 1 d . . . . .
H10A H 0.488879 -0.414261 0.670826 0.073 Uiso 1 1 calc GR . . . .
H10B H 0.634169 -0.358459 0.739076 0.073 Uiso 1 1 calc GR . . . .
H10C H 0.628089 -0.261174 0.662969 0.073 Uiso 1 1 calc GR . . . .
O3 O 0.1511(3) 0.2907(3) 1.04695(12) 0.0620(6) Uani 1 1 d . . . . .
H3 H 0.093963 0.208638 1.061870 0.093 Uiso 1 1 calc GR . . . .
C19 C 0.3453(5) 0.2704(5) 1.0664(2) 0.0733(10) Uani 1 1 d . . . . .
H19A H 0.382802 0.158330 1.050868 0.088 Uiso 1 1 calc R . . . .
H19B H 0.372989 0.276567 1.120291 0.088 Uiso 1 1 calc R . . . .
C20 C 0.4569(6) 0.3966(6) 1.0334(3) 0.0916(14) Uani 1 1 d . . . . .
H20A H 0.588687 0.386665 1.053888 0.137 Uiso 1 1 calc GR . . . .
H20B H 0.410524 0.507955 1.043745 0.137 Uiso 1 1 calc GR . . . .
H20C H 0.446100 0.379436 0.980342 0.137 Uiso 1 1 calc GR . . . .
H1A H 0.149(4) 0.542(4) 0.8971(17) 0.047(8) Uiso 1 1 d . . . . .
H1B H 0.056(5) 0.442(5) 0.9517(19) 0.059(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C14 1.354(3) . ?
O2 C9 1.213(3) . ?
O1 C8 1.226(3) . ?
N2 C1 1.482(3) . ?
N2 C6 1.405(3) . ?
N2 C5 1.472(3) . ?
N1 C2 1.473(3) . ?
N5 C18 1.146(4) . ?
N4 C6 1.391(3) . ?
N4 C9 1.390(3) . ?
N4 C11 1.463(3) . ?
N3 C9 1.383(3) . ?
N3 C8 1.393(3) . ?
N3 C10 1.465(3) . ?
C1 C2 1.523(3) . ?
C6 C7 1.341(3) . ?
C13 C12 1.390(3) . ?
C13 C14 1.381(3) . ?
C7 C8 1.433(3) . ?
C11 C12 1.515(3) . ?
C2 C3 1.516(3) . ?
C12 C17 1.397(3) . ?
C17 C18 1.435(3) . ?
C17 C16 1.397(3) . ?
C14 C15 1.370(4) . ?
C16 C15 1.368(4) . ?
C3 C4 1.515(4) . ?
C5 C4 1.521(4) . ?
O3 C19 1.393(4) . ?
C19 C20 1.452(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N2 C1 111.88(17) . . ?
C6 N2 C5 114.02(19) . . ?
C5 N2 C1 110.94(18) . . ?
C6 N4 C11 120.51(17) . . ?
C9 N4 C6 121.73(18) . . ?
C9 N4 C11 117.29(18) . . ?
C9 N3 C8 124.50(19) . . ?
C9 N3 C10 117.5(2) . . ?
C8 N3 C10 117.6(2) . . ?
N2 C1 C2 111.15(17) . . ?
N4 C6 N2 114.29(19) . . ?
C7 C6 N2 125.4(2) . . ?
C7 C6 N4 120.34(19) . . ?
O2 C9 N4 121.9(2) . . ?
O2 C9 N3 122.0(2) . . ?
N3 C9 N4 116.10(18) . . ?
C14 C13 C12 118.7(2) . . ?
C6 C7 C8 121.4(2) . . ?
N4 C11 C12 113.06(18) . . ?
N1 C2 C1 110.96(18) . . ?
N1 C2 C3 110.5(2) . . ?
C3 C2 C1 110.0(2) . . ?
C13 C12 C11 121.3(2) . . ?
C13 C12 C17 118.28(19) . . ?
C17 C12 C11 120.3(2) . . ?
C12 C17 C18 120.76(19) . . ?
C12 C17 C16 121.1(2) . . ?
C16 C17 C18 118.2(2) . . ?
O1 C8 N3 119.5(2) . . ?
O1 C8 C7 125.0(2) . . ?
N3 C8 C7 115.40(19) . . ?
N5 C18 C17 178.8(3) . . ?
F1 C14 C13 117.8(2) . . ?
F1 C14 C15 118.5(2) . . ?
C15 C14 C13 123.7(2) . . ?
C15 C16 C17 120.4(2) . . ?
C16 C15 C14 117.9(2) . . ?
C4 C3 C2 111.3(2) . . ?
N2 C5 C4 108.8(2) . . ?
C3 C4 C5 111.0(2) . . ?
O3 C19 C20 112.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C14 C15 C16 -179.2(2) . . . . ?
N2 C1 C2 N1 177.78(19) . . . . ?
N2 C1 C2 C3 55.1(3) . . . . ?
N2 C6 C7 C8 -179.5(2) . . . . ?
N2 C5 C4 C3 -58.5(3) . . . . ?
N1 C2 C3 C4 -175.4(2) . . . . ?
N4 C6 C7 C8 1.1(3) . . . . ?
N4 C11 C12 C13 -27.8(3) . . . . ?
N4 C11 C12 C17 155.32(19) . . . . ?
C1 N2 C6 N4 -91.9(2) . . . . ?
C1 N2 C6 C7 88.7(3) . . . . ?
C1 N2 C5 C4 61.3(3) . . . . ?
C1 C2 C3 C4 -52.5(3) . . . . ?
C6 N2 C1 C2 170.79(18) . . . . ?
C6 N2 C5 C4 -171.3(2) . . . . ?
C6 N4 C9 O2 175.4(2) . . . . ?
C6 N4 C9 N3 -5.4(3) . . . . ?
C6 N4 C11 C12 -70.2(2) . . . . ?
C6 C7 C8 O1 -179.6(2) . . . . ?
C6 C7 C8 N3 1.9(3) . . . . ?
C9 N4 C6 N2 -178.72(18) . . . . ?
C9 N4 C6 C7 0.7(3) . . . . ?
C9 N4 C11 C12 102.1(2) . . . . ?
C9 N3 C8 O1 174.2(2) . . . . ?
C9 N3 C8 C7 -7.2(3) . . . . ?
C13 C12 C17 C18 -179.9(2) . . . . ?
C13 C12 C17 C16 -0.1(3) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
C11 N4 C6 N2 -6.8(3) . . . . ?
C11 N4 C6 C7 172.7(2) . . . . ?
C11 N4 C9 O2 3.2(3) . . . . ?
C11 N4 C9 N3 -177.61(18) . . . . ?
C11 C12 C17 C18 -2.9(3) . . . . ?
C11 C12 C17 C16 176.9(2) . . . . ?
C2 C3 C4 C5 55.1(3) . . . . ?
C12 C13 C14 F1 179.1(2) . . . . ?
C12 C13 C14 C15 0.3(4) . . . . ?
C12 C17 C16 C15 0.0(4) . . . . ?
C17 C16 C15 C14 0.3(4) . . . . ?
C8 N3 C9 O2 -171.9(2) . . . . ?
C8 N3 C9 N4 8.9(3) . . . . ?
C18 C17 C16 C15 179.8(2) . . . . ?
C14 C13 C12 C11 -176.98(19) . . . . ?
C14 C13 C12 C17 0.0(3) . . . . ?
C5 N2 C1 C2 -60.7(2) . . . . ?
C5 N2 C6 N4 141.2(2) . . . . ?
C5 N2 C6 C7 -38.2(3) . . . . ?
C10 N3 C9 O2 0.0(3) . . . . ?
C10 N3 C9 N4 -179.2(2) . . . . ?
C10 N3 C8 O1 2.3(3) . . . . ?
C10 N3 C8 C7 -179.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9(2)
2 0.1(2)

####################################################################### 
# 
# 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_MeOH
_audit_block_doi                 10.5517/ccdc.csd.cc259y1h
_database_code_depnum_ccdc_archive 'CCDC 2005546'
loop_
_audit_author_name
_audit_author_address
'Kailin Xu'
;Guangdong University of Technology
China
;
_audit_update_record             
;
2020-09-12 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;
_audit_creation_date             2019-09-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 F N5 O2, C H4 O'
_chemical_formula_sum            'C19 H24 F N5 O3'
_chemical_formula_weight         389.43
_chemical_absolute_configuration rmad
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.9625(2)
_cell_length_b                   7.9457(2)
_cell_length_c                   17.9395(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.3390(10)
_cell_angle_gamma                90
_cell_volume                     989.60(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    241(2)
_cell_measurement_theta_max      72.29
_cell_measurement_theta_min      9.93
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6283
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1178 before and 0.0710 after correction.
The Ratio of minimum to maximum transmission is 0.8337.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18882
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.284
_diffrn_reflns_theta_min         8.373
_diffrn_ambient_temperature      240.83
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.823
_reflns_Friedel_fraction_full    0.950
_reflns_Friedel_fraction_max     0.937
_reflns_number_gt                3653
_reflns_number_total             3750
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (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         0.120
_refine_diff_density_min         -0.110
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details 
;
 Flack x determined using 1608 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3750
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0293
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0372P)²+0.1327P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0736
_refine_ls_wR_factor_ref         0.0746
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1C,H1D), C11(H11A,H11B), C5(H5A,H5B), C3(H3A,H3B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C7(H7), C16(H16), C15(H15)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.78175(18) 0.20166(17) 0.49456(8) 0.0548(4) Uani 1 1 d . . . . .
O2 O 0.0451(2) 0.2747(2) 0.36927(8) 0.0514(4) Uani 1 1 d . . . . .
N4 N 0.2702(2) 0.35192(19) 0.29058(8) 0.0307(3) Uani 1 1 d . . . . .
N2 N 0.5161(2) 0.43408(19) 0.21540(8) 0.0333(3) Uani 1 1 d . . . . .
O1 O 0.1807(2) -0.09234(19) 0.18740(10) 0.0550(4) Uani 1 1 d . . . . .
O3 O 0.6826(3) 1.0927(2) 0.04647(10) 0.0657(5) Uani 1 1 d . . . . .
N3 N 0.1009(2) 0.0973(2) 0.27409(9) 0.0349(3) Uani 1 1 d . . . . .
N5 N 0.4691(3) 0.9367(2) 0.35595(12) 0.0564(5) Uani 1 1 d . . . . .
N1 N 0.4920(3) 0.8054(2) 0.08395(10) 0.0449(4) Uani 1 1 d . . . . .
C6 C 0.3816(2) 0.3105(2) 0.23221(9) 0.0300(4) Uani 1 1 d . . . . .
C1 C 0.4365(2) 0.5473(2) 0.15561(10) 0.0339(4) Uani 1 1 d . . . . .
H1C H 0.310746 0.589229 0.168343 0.041 Uiso 1 1 calc R . . . .
H1D H 0.417387 0.484093 0.108715 0.041 Uiso 1 1 calc R . . . .
C13 C 0.5583(3) 0.3484(2) 0.41481(10) 0.0348(4) Uani 1 1 d . . . . .
H13 H 0.497421 0.246451 0.400769 0.042 Uiso 1 1 calc R . . . .
C9 C 0.1332(2) 0.2428(2) 0.31523(10) 0.0337(4) Uani 1 1 d . . . . .
C7 C 0.3555(3) 0.1620(3) 0.19684(11) 0.0391(4) Uani 1 1 d . . . . .
H7 H 0.432947 0.134868 0.157848 0.047 Uiso 1 1 calc R . . . .
C11 C 0.3081(2) 0.5075(2) 0.33308(10) 0.0331(4) Uani 1 1 d . . . . .
H11A H 0.198221 0.531130 0.362517 0.040 Uiso 1 1 calc R . . . .
H11B H 0.319382 0.600918 0.297999 0.040 Uiso 1 1 calc R . . . .
C12 C 0.4897(2) 0.4994(2) 0.38520(9) 0.0301(4) Uani 1 1 d . . . . .
C18 C 0.5198(3) 0.8078(3) 0.37833(11) 0.0397(4) Uani 1 1 d . . . . .
C2 C 0.5703(3) 0.6960(2) 0.14469(11) 0.0380(4) Uani 1 1 d . . . . .
H2 H 0.581049 0.762626 0.191459 0.046 Uiso 1 1 calc R . . . .
C8 C 0.2128(3) 0.0445(2) 0.21711(11) 0.0385(4) Uani 1 1 d . . . . .
C17 C 0.5854(3) 0.6480(2) 0.40722(10) 0.0335(4) Uani 1 1 d . . . . .
C14 C 0.7180(3) 0.3503(3) 0.46542(10) 0.0390(4) Uani 1 1 d . . . . .
C16 C 0.7465(3) 0.6447(3) 0.45878(11) 0.0427(5) Uani 1 1 d . . . . .
H16 H 0.808863 0.745661 0.473401 0.051 Uiso 1 1 calc R . . . .
C15 C 0.8135(3) 0.4944(3) 0.48806(11) 0.0456(5) Uani 1 1 d . . . . .
H15 H 0.921796 0.490367 0.522638 0.055 Uiso 1 1 calc R . . . .
C5 C 0.7044(3) 0.3656(3) 0.19798(14) 0.0490(5) Uani 1 1 d . . . . .
H5A H 0.689995 0.300748 0.151413 0.059 Uiso 1 1 calc R . . . .
H5B H 0.753999 0.290111 0.238163 0.059 Uiso 1 1 calc R . . . .
C3 C 0.7693(3) 0.6328(3) 0.12998(14) 0.0497(5) Uani 1 1 d . . . . .
H3A H 0.857826 0.728506 0.128772 0.060 Uiso 1 1 calc R . . . .
H3B H 0.764018 0.577506 0.081048 0.060 Uiso 1 1 calc R . . . .
C10 C -0.0449(3) -0.0194(3) 0.29808(14) 0.0505(5) Uani 1 1 d . . . . .
H10A H 0.017934 -0.112280 0.325215 0.076 Uiso 1 1 calc GR . . . .
H10B H -0.120632 -0.062279 0.254586 0.076 Uiso 1 1 calc GR . . . .
H10C H -0.128542 0.039084 0.330323 0.076 Uiso 1 1 calc GR . . . .
C4 C 0.8446(3) 0.5097(3) 0.18981(16) 0.0575(6) Uani 1 1 d . . . . .
H4A H 0.865588 0.568792 0.237672 0.069 Uiso 1 1 calc R . . . .
H4B H 0.968661 0.464489 0.176777 0.069 Uiso 1 1 calc R . . . .
C19 C 0.8762(4) 1.0721(5) 0.0316(2) 0.0885(10) Uani 1 1 d . . . . .
H19A H 0.903849 1.141536 -0.010749 0.133 Uiso 1 1 calc GR . . . .
H19B H 0.899848 0.954918 0.020149 0.133 Uiso 1 1 calc GR . . . .
H19C H 0.958580 1.105512 0.075079 0.133 Uiso 1 1 calc GR . . . .
H1A H 0.471(3) 0.743(4) 0.0424(15) 0.047(6) Uiso 1 1 d . . . . .
H1B H 0.381(4) 0.847(4) 0.0959(14) 0.052(7) Uiso 1 1 d . . . . .
H3 H 0.635(4) 1.000(4) 0.0625(16) 0.069(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C14 1.353(2) . ?
O2 C9 1.213(2) . ?
N4 C6 1.389(2) . ?
N4 C9 1.386(2) . ?
N4 C11 1.466(2) . ?
N2 C6 1.405(2) . ?
N2 C1 1.475(2) . ?
N2 C5 1.475(2) . ?
O1 C8 1.224(2) . ?
O3 C19 1.403(4) . ?
O3 H3 0.87(3) . ?
N3 C9 1.381(2) . ?
N3 C8 1.396(3) . ?
N3 C10 1.463(2) . ?
N5 C18 1.146(3) . ?
N1 C2 1.466(3) . ?
N1 H1A 0.90(3) . ?
N1 H1B 0.88(3) . ?
C6 C7 1.345(3) . ?
C1 H1C 0.9800 . ?
C1 H1D 0.9800 . ?
C1 C2 1.527(2) . ?
C13 H13 0.9400 . ?
C13 C12 1.382(3) . ?
C13 C14 1.382(3) . ?
C7 H7 0.9400 . ?
C7 C8 1.431(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 C12 1.516(2) . ?
C12 C17 1.398(2) . ?
C18 C17 1.433(3) . ?
C2 H2 0.9900 . ?
C2 C3 1.515(3) . ?
C17 C16 1.399(3) . ?
C14 C15 1.370(3) . ?
C16 H16 0.9400 . ?
C16 C15 1.373(3) . ?
C15 H15 0.9400 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 C4 1.519(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 C4 1.516(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N4 C11 120.21(14) . . ?
C9 N4 C6 121.97(15) . . ?
C9 N4 C11 117.56(14) . . ?
C6 N2 C1 111.23(13) . . ?
C6 N2 C5 113.89(15) . . ?
C5 N2 C1 111.23(15) . . ?
C19 O3 H3 111(2) . . ?
C9 N3 C8 124.45(15) . . ?
C9 N3 C10 117.51(16) . . ?
C8 N3 C10 117.58(17) . . ?
C2 N1 H1A 108.5(17) . . ?
C2 N1 H1B 109.1(17) . . ?
H1A N1 H1B 108(2) . . ?
N4 C6 N2 114.54(15) . . ?
C7 C6 N4 120.01(16) . . ?
C7 C6 N2 125.45(16) . . ?
N2 C1 H1C 109.3 . . ?
N2 C1 H1D 109.3 . . ?
N2 C1 C2 111.46(14) . . ?
H1C C1 H1D 108.0 . . ?
C2 C1 H1C 109.3 . . ?
C2 C1 H1D 109.3 . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C14 C13 C12 118.73(18) . . ?
O2 C9 N4 121.77(17) . . ?
O2 C9 N3 122.03(17) . . ?
N3 C9 N4 116.20(15) . . ?
C6 C7 H7 119.2 . . ?
C6 C7 C8 121.61(17) . . ?
C8 C7 H7 119.2 . . ?
N4 C11 H11A 108.9 . . ?
N4 C11 H11B 108.9 . . ?
N4 C11 C12 113.19(14) . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C13 C12 C11 121.44(16) . . ?
C13 C12 C17 118.75(14) . . ?
C17 C12 C11 119.73(16) . . ?
N5 C18 C17 179.0(2) . . ?
N1 C2 C1 111.00(15) . . ?
N1 C2 H2 108.2 . . ?
N1 C2 C3 111.11(17) . . ?
C1 C2 H2 108.2 . . ?
C3 C2 C1 109.91(16) . . ?
C3 C2 H2 108.2 . . ?
O1 C8 N3 119.51(17) . . ?
O1 C8 C7 125.20(18) . . ?
N3 C8 C7 115.27(16) . . ?
C12 C17 C18 120.94(15) . . ?
C12 C17 C16 120.82(17) . . ?
C16 C17 C18 118.24(17) . . ?
F1 C14 C13 117.96(18) . . ?
F1 C14 C15 118.52(16) . . ?
C15 C14 C13 123.51(18) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 C17 120.10(19) . . ?
C15 C16 H16 120.0 . . ?
C14 C15 C16 118.08(16) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 H15 121.0 . . ?
N2 C5 H5A 109.8 . . ?
N2 C5 H5B 109.8 . . ?
N2 C5 C4 109.27(18) . . ?
H5A C5 H5B 108.3 . . ?
C4 C5 H5A 109.8 . . ?
C4 C5 H5B 109.8 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C2 C3 C4 111.24(17) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C3 C4 C5 111.39(17) . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_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_cu_xukl_20200907_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc259y3k
_database_code_depnum_ccdc_archive 'CCDC 2005548'
_audit_update_record             
;
2020-10-25 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;
_audit_creation_date             2020-10-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 F N5 O2'
_chemical_formula_sum            'C18 H20 F N5 O2'
_chemical_formula_weight         357.39
_chemical_absolute_configuration rmad
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.1057(2)
_cell_length_b                   7.8894(2)
_cell_length_c                   15.5407(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.3250(10)
_cell_angle_gamma                90
_cell_volume                     864.10(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    240(2)
_cell_measurement_theta_max      72.24
_cell_measurement_theta_min      5.74
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.834
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1501 before and 0.0759 after correction.
The Ratio of minimum to maximum transmission is 0.7890.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13425
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.235
_diffrn_reflns_theta_min         2.867
_diffrn_ambient_temperature      240.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_full    0.952
_reflns_Friedel_fraction_max     0.937
_reflns_number_gt                3274
_reflns_number_total             3301
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1443 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3301
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0292
_refine_ls_restrained_S_all      0.915
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0551P)²+0.1153P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0790
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C1(H1C,H1D), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C7(H7), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.78647(18) 0.72553(17) 0.50718(9) 0.0525(3) Uani 1 1 d . . . . .
O2 O 0.11598(19) 0.6500(2) 0.64885(9) 0.0467(4) Uani 1 1 d . . . . .
N4 N 0.37945(19) 0.57444(18) 0.73991(9) 0.0277(3) Uani 1 1 d . . . . .
O1 O 0.3381(2) 1.0181(2) 0.86188(13) 0.0565(4) Uani 1 1 d . . . . .
N2 N 0.66164(19) 0.49468(19) 0.82555(9) 0.0290(3) Uani 1 1 d . . . . .
N3 N 0.2186(2) 0.8286(2) 0.75987(10) 0.0332(3) Uani 1 1 d . . . . .
C12 C 0.5493(2) 0.4258(2) 0.63124(10) 0.0279(3) Uani 1 1 d . . . . .
N5 N 0.5405(3) -0.0140(2) 0.66454(14) 0.0541(5) Uani 1 1 d . . . . .
C6 C 0.5192(2) 0.6174(2) 0.80728(10) 0.0277(3) Uani 1 1 d . . . . .
C13 C 0.6031(2) 0.5781(2) 0.59754(11) 0.0325(4) Uani 1 1 d . . . . .
H13 H 0.549387 0.680756 0.613111 0.039 Uiso 1 1 calc R . . . .
C7 C 0.5108(3) 0.7660(3) 0.84866(12) 0.0366(4) Uani 1 1 d . . . . .
H7 H 0.607652 0.794572 0.893275 0.044 Uiso 1 1 calc R . . . .
C11 C 0.3957(2) 0.4177(2) 0.69039(11) 0.0301(3) Uani 1 1 d . . . . .
H11A H 0.273738 0.394663 0.655323 0.036 Uiso 1 1 calc R . . . .
H11B H 0.422870 0.323255 0.731029 0.036 Uiso 1 1 calc R . . . .
C9 C 0.2305(2) 0.6826(2) 0.71176(11) 0.0313(4) Uani 1 1 d . . . . .
N1 N 0.7216(3) 0.1079(3) 0.96922(13) 0.0494(4) Uani 1 1 d . . . . .
H1A H 0.742(4) 0.167(5) 1.021(2) 0.074 Uiso 1 1 d R . . . .
H1B H 0.596(5) 0.079(5) 0.961(2) 0.074 Uiso 1 1 d R . . . .
C18 C 0.5811(3) 0.1153(3) 0.63936(12) 0.0376(4) Uani 1 1 d . . . . .
C8 C 0.3570(3) 0.8823(3) 0.82621(13) 0.0374(4) Uani 1 1 d . . . . .
C14 C 0.7375(3) 0.5764(3) 0.54047(12) 0.0363(4) Uani 1 1 d . . . . .
C17 C 0.6329(2) 0.2762(2) 0.60631(11) 0.0309(3) Uani 1 1 d . . . . .
C1 C 0.6206(2) 0.3762(2) 0.89407(11) 0.0316(4) Uani 1 1 d . . . . .
H1C H 0.489632 0.335660 0.881445 0.038 Uiso 1 1 calc R . . . .
H1D H 0.633059 0.435587 0.949898 0.038 Uiso 1 1 calc R . . . .
C2 C 0.7561(3) 0.2251(2) 0.90019(12) 0.0339(4) Uani 1 1 d . . . . .
H2 H 0.735570 0.163069 0.844424 0.041 Uiso 1 1 calc R . . . .
C3 C 0.9606(3) 0.2873(3) 0.91351(13) 0.0398(4) Uani 1 1 d . . . . .
H3A H 0.988085 0.338071 0.971305 0.048 Uiso 1 1 calc R . . . .
H3B H 1.046329 0.190837 0.910468 0.048 Uiso 1 1 calc R . . . .
C4 C 0.9959(2) 0.4169(3) 0.84559(14) 0.0435(4) Uani 1 1 d . . . . .
H4A H 0.984555 0.362262 0.788545 0.052 Uiso 1 1 calc R . . . .
H4B H 1.125378 0.461035 0.858539 0.052 Uiso 1 1 calc R . . . .
C15 C 0.8212(3) 0.4307(3) 0.51488(12) 0.0430(5) Uani 1 1 d . . . . .
H15 H 0.911953 0.434700 0.475878 0.052 Uiso 1 1 calc R . . . .
C5 C 0.8553(3) 0.5633(3) 0.84302(14) 0.0403(4) Uani 1 1 d . . . . .
H5A H 0.871273 0.623329 0.898685 0.048 Uiso 1 1 calc R . . . .
H5B H 0.878029 0.643686 0.797398 0.048 Uiso 1 1 calc R . . . .
C16 C 0.7682(3) 0.2795(3) 0.54805(12) 0.0405(4) Uani 1 1 d . . . . .
H16 H 0.822634 0.177806 0.531692 0.049 Uiso 1 1 calc R . . . .
C10 C 0.0624(3) 0.9453(3) 0.73210(16) 0.0479(5) Uani 1 1 d . . . . .
H10A H 0.110099 1.041270 0.702390 0.072 Uiso 1 1 calc GR . . . .
H10B H 0.007422 0.985002 0.782455 0.072 Uiso 1 1 calc GR . . . .
H10C H -0.033777 0.887035 0.693068 0.072 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C14 1.349(2) . ?
O2 C9 1.217(2) . ?
N4 C6 1.390(2) . ?
N4 C11 1.469(2) . ?
N4 C9 1.386(2) . ?
O1 C8 1.222(3) . ?
N2 C6 1.403(2) . ?
N2 C1 1.474(2) . ?
N2 C5 1.471(2) . ?
N3 C9 1.382(2) . ?
N3 C8 1.397(3) . ?
N3 C10 1.464(2) . ?
C12 C13 1.384(2) . ?
C12 C11 1.516(2) . ?
C12 C17 1.398(2) . ?
N5 C18 1.142(3) . ?
C6 C7 1.343(3) . ?
C13 H13 0.9400 . ?
C13 C14 1.384(3) . ?
C7 H7 0.9400 . ?
C7 C8 1.435(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
N1 H1A 0.93(4) . ?
N1 H1B 0.91(4) . ?
N1 C2 1.460(3) . ?
C18 C17 1.435(3) . ?
C14 C15 1.376(3) . ?
C17 C16 1.402(3) . ?
C1 H1C 0.9800 . ?
C1 H1D 0.9800 . ?
C1 C2 1.527(2) . ?
C2 H2 0.9900 . ?
C2 C3 1.522(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 C4 1.513(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 C5 1.524(3) . ?
C15 H15 0.9400 . ?
C15 C16 1.371(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C16 H16 0.9400 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N4 C11 120.24(13) . . ?
C9 N4 C6 122.09(14) . . ?
C9 N4 C11 117.42(14) . . ?
C6 N2 C1 112.31(12) . . ?
C6 N2 C5 114.65(14) . . ?
C5 N2 C1 111.50(14) . . ?
C9 N3 C8 124.49(15) . . ?
C9 N3 C10 117.47(16) . . ?
C8 N3 C10 117.57(16) . . ?
C13 C12 C11 121.40(15) . . ?
C13 C12 C17 118.74(14) . . ?
C17 C12 C11 119.78(15) . . ?
N4 C6 N2 114.33(14) . . ?
C7 C6 N4 120.17(15) . . ?
C7 C6 N2 125.50(16) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 C12 118.70(17) . . ?
C14 C13 H13 120.7 . . ?
C6 C7 H7 119.3 . . ?
C6 C7 C8 121.39(16) . . ?
C8 C7 H7 119.3 . . ?
N4 C11 C12 113.15(13) . . ?
N4 C11 H11A 108.9 . . ?
N4 C11 H11B 108.9 . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.8 . . ?
O2 C9 N4 121.93(17) . . ?
O2 C9 N3 122.01(16) . . ?
N4 C9 N3 116.05(14) . . ?
H1A N1 H1B 106(3) . . ?
C2 N1 H1A 108(2) . . ?
C2 N1 H1B 108(2) . . ?
N5 C18 C17 179.0(2) . . ?
O1 C8 N3 119.54(17) . . ?
O1 C8 C7 125.08(18) . . ?
N3 C8 C7 115.35(16) . . ?
F1 C14 C13 118.03(18) . . ?
F1 C14 C15 118.40(16) . . ?
C15 C14 C13 123.56(17) . . ?
C12 C17 C18 120.70(15) . . ?
C12 C17 C16 120.89(17) . . ?
C16 C17 C18 118.41(17) . . ?
N2 C1 H1C 109.4 . . ?
N2 C1 H1D 109.4 . . ?
N2 C1 C2 111.02(13) . . ?
H1C C1 H1D 108.0 . . ?
C2 C1 H1C 109.4 . . ?
C2 C1 H1D 109.4 . . ?
N1 C2 C1 112.10(15) . . ?
N1 C2 H2 108.1 . . ?
N1 C2 C3 110.54(16) . . ?
C1 C2 H2 108.1 . . ?
C3 C2 C1 109.88(15) . . ?
C3 C2 H2 108.1 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 C2 111.30(15) . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
C3 C4 C5 111.32(15) . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C14 C15 H15 121.0 . . ?
C16 C15 C14 117.91(15) . . ?
C16 C15 H15 121.0 . . ?
N2 C5 C4 108.71(17) . . ?
N2 C5 H5A 109.9 . . ?
N2 C5 H5B 109.9 . . ?
C4 C5 H5A 109.9 . . ?
C4 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
C17 C16 H16 119.9 . . ?
C15 C16 C17 120.20(18) . . ?
C15 C16 H16 119.9 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
