# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_NDI-744_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1834665'
_audit_update_record             
;
2018-04-04 deposited with the CCDC.
2018-09-19 downloaded from the CCDC.
;
_audit_creation_date             02/21/2018
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'compound 5aa'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H18 F3 N O2'
_chemical_formula_weight         373.36

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.515(2)
_cell_length_b                   7.832(2)
_cell_length_c                   36.046(7)
_cell_angle_alpha                90.00(3)
_cell_angle_beta                 90.00(3)
_cell_angle_gamma                90.00(3)
_cell_volume                     1839.0(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    528
_cell_measurement_theta_min      1.55
_cell_measurement_theta_max      25.50

_exptl_crystal_description       stick
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   .975
_exptl_transmission_factor_max   .979
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9899
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         3.178
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3557
_reflns_number_gt                3320
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.692
_reflns_Friedel_fraction_max     0.983
_reflns_Friedel_fraction_full    0.996

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0308P)²+0.2587P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.093(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1253 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(18)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3557
_refine_ls_number_parameters     251
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0774
_refine_ls_wR_factor_gt          0.0760
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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
F3 F 0.0986(2) 0.8129(2) 0.40601(4) 0.0707(4) Uani 1 1 d . . . . .
O2 O 0.5127(3) 0.86587(19) 0.38953(4) 0.0502(4) Uani 1 1 d . . . . .
H2O H 0.5272 0.8414 0.4115 0.075 Uiso 1 1 calc R U . . .
O1 O 0.5753(2) 0.7362(2) 0.45872(4) 0.0507(4) Uani 1 1 d . . . . .
F1 F 0.0516(2) 0.6843(2) 0.35423(4) 0.0739(5) Uani 1 1 d . . . . .
F2 F 0.1490(3) 0.9465(2) 0.35521(4) 0.0750(5) Uani 1 1 d . . . . .
N1 N 0.8740(3) 0.6118(2) 0.47792(4) 0.0439(4) Uani 1 1 d . . . . .
C8 C 1.0069(3) 0.4827(3) 0.46640(5) 0.0422(5) Uani 1 1 d . . . . .
C1 C 0.7122(3) 0.6282(3) 0.45497(5) 0.0394(5) Uani 1 1 d . . . . .
C2 C 0.7380(3) 0.4977(2) 0.42488(5) 0.0364(4) Uani 1 1 d . . . . .
C9 C 0.6103(3) 0.4781(2) 0.39596(5) 0.0380(4) Uani 1 1 d . . . . .
C3 C 0.9281(3) 0.4068(3) 0.43441(5) 0.0406(5) Uani 1 1 d . . . . .
C10 C 0.4048(3) 0.5661(3) 0.39308(5) 0.0412(5) Uani 1 1 d . . . . .
H10A H 0.3544 0.5862 0.4180 0.049 Uiso 1 1 calc R U . . .
H10B H 0.3097 0.4882 0.3811 0.049 Uiso 1 1 calc R U . . .
C14 C 0.6919(3) 0.7966(3) 0.27884(5) 0.0419(5) Uani 1 1 d . . . . .
C13 C 0.6225(3) 0.8042(3) 0.31757(5) 0.0420(5) Uani 1 1 d . . . . .
H13 H 0.6960 0.8752 0.3334 0.050 Uiso 1 1 calc R U . . .
C12 C 0.4670(3) 0.7208(3) 0.33206(5) 0.0434(5) Uani 1 1 d . . . . .
H12 H 0.3943 0.6465 0.3168 0.052 Uiso 1 1 calc R U . . .
C11 C 0.3989(3) 0.7377(3) 0.37180(5) 0.0419(5) Uani 1 1 d . . . . .
C7 C 1.1863(4) 0.4309(3) 0.48328(7) 0.0546(6) Uani 1 1 d . . . . .
H7 H 1.2362 0.4855 0.5043 0.066 Uiso 1 1 calc R U . . .
C4 C 1.0312(4) 0.2661(3) 0.42011(7) 0.0568(6) Uani 1 1 d . . . . .
H4 H 0.9802 0.2087 0.3995 0.068 Uiso 1 1 calc R U . . .
C15 C 0.8571(4) 0.8938(4) 0.26782(7) 0.0602(6) Uani 1 1 d . . . . .
H15 H 0.9244 0.9615 0.2852 0.072 Uiso 1 1 calc R U . . .
C19 C 0.5984(4) 0.6953(3) 0.25214(6) 0.0543(6) Uani 1 1 d . . . . .
H19 H 0.4873 0.6271 0.2587 0.065 Uiso 1 1 calc R U . . .
C17 C 0.8301(5) 0.7926(4) 0.20579(6) 0.0659(7) Uani 1 1 d . . . . .
H17 H 0.8758 0.7911 0.1814 0.079 Uiso 1 1 calc R U . . .
C6 C 1.2883(4) 0.2950(4) 0.46766(8) 0.0661(7) Uani 1 1 d . . . . .
H6 H 1.4115 0.2583 0.4780 0.079 Uiso 1 1 calc R U . . .
C16 C 0.9254(5) 0.8927(4) 0.23135(7) 0.0727(8) Uani 1 1 d . . . . .
H16 H 1.0362 0.9605 0.2244 0.087 Uiso 1 1 calc R U . . .
C20 C 0.6563(4) 0.3536(3) 0.36543(6) 0.0609(7) Uani 1 1 d . . . . .
H20A H 0.7996 0.3588 0.3594 0.091 Uiso 1 1 calc R U . . .
H20B H 0.5764 0.3821 0.3439 0.091 Uiso 1 1 calc R U . . .
H20C H 0.6221 0.2402 0.3735 0.091 Uiso 1 1 calc R U . . .
C5 C 1.2111(4) 0.2125(3) 0.43703(9) 0.0699(8) Uani 1 1 d . . . . .
H5 H 1.2810 0.1188 0.4275 0.084 Uiso 1 1 calc R U . . .
C21 C 0.1738(4) 0.7945(3) 0.37183(6) 0.0551(6) Uani 1 1 d . . . . .
C18 C 0.6679(5) 0.6948(4) 0.21611(6) 0.0637(7) Uani 1 1 d . . . . .
H18 H 0.6029 0.6264 0.1986 0.076 Uiso 1 1 calc R U . . .
H1N H 0.895(4) 0.681(3) 0.4970(7) 0.059(7) 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
F3 C21 1.334(3) . ?
O2 C11 1.402(3) . ?
O2 H2O 0.8200 . ?
O1 C1 1.236(2) . ?
F1 C21 1.334(3) . ?
F2 C21 1.342(3) . ?
N1 C1 1.346(3) . ?
N1 C8 1.394(3) . ?
N1 H1N 0.88(2) . ?
C8 C7 1.379(3) . ?
C8 C3 1.395(3) . ?
C1 C2 1.500(3) . ?
C2 C9 1.343(3) . ?
C2 C3 1.469(3) . ?
C9 C20 1.501(3) . ?
C9 C10 1.509(3) . ?
C3 C4 1.390(3) . ?
C10 C11 1.548(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C14 C15 1.377(3) . ?
C14 C19 1.388(3) . ?
C14 C13 1.469(3) . ?
C13 C12 1.314(3) . ?
C13 H13 0.9300 . ?
C12 C11 1.505(3) . ?
C12 H12 0.9300 . ?
C11 C21 1.533(3) . ?
C7 C6 1.376(4) . ?
C7 H7 0.9300 . ?
C4 C5 1.386(4) . ?
C4 H4 0.9300 . ?
C15 C16 1.388(3) . ?
C15 H15 0.9300 . ?
C19 C18 1.376(3) . ?
C19 H19 0.9300 . ?
C17 C18 1.357(4) . ?
C17 C16 1.360(4) . ?
C17 H17 0.9300 . ?
C6 C5 1.374(4) . ?
C6 H6 0.9300 . ?
C16 H16 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C5 H5 0.9300 . ?
C18 H18 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
C11 O2 H2O 109.5 . . ?
C1 N1 C8 111.85(17) . . ?
C1 N1 H1N 122.8(17) . . ?
C8 N1 H1N 125.2(17) . . ?
C7 C8 N1 127.5(2) . . ?
C7 C8 C3 123.4(2) . . ?
N1 C8 C3 109.08(17) . . ?
O1 C1 N1 124.25(18) . . ?
O1 C1 C2 128.77(18) . . ?
N1 C1 C2 106.95(17) . . ?
C9 C2 C3 130.43(18) . . ?
C9 C2 C1 124.73(18) . . ?
C3 C2 C1 104.82(16) . . ?
C2 C9 C20 121.33(19) . . ?
C2 C9 C10 123.44(17) . . ?
C20 C9 C10 115.04(18) . . ?
C4 C3 C8 117.8(2) . . ?
C4 C3 C2 134.8(2) . . ?
C8 C3 C2 107.26(17) . . ?
C9 C10 C11 116.90(17) . . ?
C9 C10 H10A 108.1 . . ?
C11 C10 H10A 108.1 . . ?
C9 C10 H10B 108.1 . . ?
C11 C10 H10B 108.1 . . ?
H10A C10 H10B 107.3 . . ?
C15 C14 C19 117.3(2) . . ?
C15 C14 C13 119.5(2) . . ?
C19 C14 C13 123.2(2) . . ?
C12 C13 C14 126.5(2) . . ?
C12 C13 H13 116.7 . . ?
C14 C13 H13 116.7 . . ?
C13 C12 C11 124.16(19) . . ?
C13 C12 H12 117.9 . . ?
C11 C12 H12 117.9 . . ?
O2 C11 C12 109.94(17) . . ?
O2 C11 C21 107.33(18) . . ?
C12 C11 C21 107.94(17) . . ?
O2 C11 C10 112.50(15) . . ?
C12 C11 C10 112.81(17) . . ?
C21 C11 C10 106.00(18) . . ?
C6 C7 C8 117.2(2) . . ?
C6 C7 H7 121.4 . . ?
C8 C7 H7 121.4 . . ?
C5 C4 C3 119.0(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C14 C15 C16 121.4(2) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C18 C19 C14 120.8(2) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
C18 C17 C16 119.7(2) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C5 C6 C7 121.1(2) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C17 C16 C15 119.9(3) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C9 C20 H20A 109.5 . . ?
C9 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C9 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C6 C5 C4 121.4(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
F3 C21 F1 106.9(2) . . ?
F3 C21 F2 105.8(2) . . ?
F1 C21 F2 106.85(19) . . ?
F3 C21 C11 112.54(18) . . ?
F1 C21 C11 112.5(2) . . ?
F2 C21 C11 111.8(2) . . ?
C17 C18 C19 120.9(2) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?

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
N1 H1N O1 0.88(2) 2.09(3) 2.890(2) 151(2) 4_566
C10 H10A O1 0.97 2.37 2.934(3) 116.7 .
O2 H2O O1 0.82 1.92 2.724(2) 167.6 .
N1 H1N O1 0.88(2) 2.09(3) 2.890(2) 151(2) 4_566
C10 H10A O1 0.97 2.37 2.934(3) 116.7 .
O2 H2O O1 0.82 1.92 2.724(2) 167.6 .
N1 H1N O1 0.88(2) 2.09(3) 2.890(2) 151(2) 4_566
C10 H10A O1 0.97 2.37 2.934(3) 116.7 .
O2 H2O O1 0.82 1.92 2.724(2) 167.6 .
N1 H1N O1 0.88(2) 2.09(3) 2.890(2) 151(2) 4_566
C10 H10A O1 0.97 2.37 2.934(3) 116.7 .
O2 H2O O1 0.82 1.92 2.724(2) 167.6 .
O2 H2O O1 0.82 1.92 2.724(2) 167.6 .
C10 H10A O1 0.97 2.37 2.934(3) 116.7 .
N1 H1N O1 0.88(2) 2.09(3) 2.890(2) 151(2) 4_566
O2 H2O O1 0.82 1.92 2.724(2) 167.6 .
C10 H10A O1 0.97 2.37 2.934(3) 116.7 .
N1 H1N O1 0.88(2) 2.09(3) 2.890(2) 151(2) 4_566
O2 H2O O1 0.82 1.92 2.724(2) 167.6 .
C10 H10A O1 0.97 2.37 2.934(3) 116.7 .
N1 H1N O1 0.88(2) 2.09(3) 2.890(2) 151(2) 4_566
O2 H2O O1 0.82 1.92 2.724(2) 167.6 .
C10 H10A O1 0.97 2.37 2.934(3) 116.7 .
N1 H1N O1 0.88(2) 2.09(3) 2.890(2) 151(2) 4_566

_refine_diff_density_max         0.131
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.024



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
