# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_capNFF_7_A
_database_code_depnum_ccdc_archive 'CCDC 1904300'
loop_
_audit_author_name
_audit_author_address
'Ann Chippindale'
;University of Reading
United Kingdom
;
_audit_update_record             
;
2019-03-20 deposited with the CCDC.	2019-04-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            CapNFF
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H23 N3 O3'
_chemical_formula_sum            'C20 H23 N3 O3'
_chemical_formula_weight         353.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0029 0.0015 '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 0.0056 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0101 0.0057 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   23.73549(11)
_cell_length_b                   16.75238(8)
_cell_length_c                   4.78477(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1902.549(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    19655
_cell_measurement_theta_max      34.444
_cell_measurement_theta_min      1.435

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.049
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   1.000
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CCP4 7.0.062: AIMLESS, version 0.7.2 : 27/05/18
Scaling & analysis of unmerged intensities, absorption correction using
spherical harmonics
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.6889
_diffrn_detector                 'Photon counting pixel array'
_diffrn_radiation_type           Synchrotron
_diffrn_measurement_device       'Fixed χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_source         'Diamond Light Source Beamline I19-1'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_detector_area_resol_mean 0
_diffrn_reflns_number            41114
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.663
_diffrn_reflns_theta_max         36.020
_diffrn_reflns_theta_full        30.000
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9215
_reflns_number_gt                7635
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.781
_reflns_Friedel_fraction_max     0.898
_reflns_Friedel_fraction_full    0.998

_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       
;
GDA-9.9.0 - generic data aquisition software
;
_computing_cell_refinement       
;
'DIALS 2theta refinement, DIALS 1.11.3-g5e171c4fa-release'
;
_computing_data_reduction        
;
aimless (Evans, P. R. and Murshudov, G. N., 2013)
ccp4 (Winn, M. D. et al., 2011)
DIALS 1.11.3-g5e171c4fa-release (Winter, G. et al., 2018)
pointless (Evans, P., 2006)
XIA2 0.5.655-g749651b0-dials-1.11 (Winter, G., 2010)
;
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_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)+(0.0548P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2932 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         9215
_refine_ls_number_parameters     327
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0942
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_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
C1 C 0.45604(5) 0.23426(7) 0.3530(3) 0.0263(2) Uani 1 1 d . . . . .
H1 H 0.4173(7) 0.2126(10) 0.381(4) 0.034(4) Uiso 1 1 d . . . . .
C2 C 0.49366(6) 0.19819(8) 0.1691(3) 0.0321(3) Uani 1 1 d . . . . .
H2 H 0.4817(9) 0.1520(12) 0.060(5) 0.047(5) Uiso 1 1 d . . . . .
C3 C 0.54691(6) 0.23077(9) 0.1265(3) 0.0323(3) Uani 1 1 d . . . . .
H3 H 0.5715(8) 0.2075(12) -0.005(5) 0.046(5) Uiso 1 1 d . . . . .
C4 C 0.56240(5) 0.29874(9) 0.2704(3) 0.0328(3) Uani 1 1 d . . . . .
H4 H 0.6011(8) 0.3209(12) 0.243(5) 0.044(5) Uiso 1 1 d . . . . .
C5 C 0.52504(5) 0.33495(8) 0.4542(3) 0.0285(2) Uani 1 1 d . . . . .
H5 H 0.5357(7) 0.3808(11) 0.556(4) 0.037(5) Uiso 1 1 d . . . . .
C6 C 0.47148(4) 0.30313(7) 0.4963(2) 0.02175(19) Uani 1 1 d . . . . .
C7 C 0.43103(5) 0.34246(8) 0.6974(3) 0.0248(2) Uani 1 1 d . . . . .
H7A H 0.4230(7) 0.3087(10) 0.860(4) 0.030(4) Uiso 1 1 d . . . . .
H7B H 0.4477(7) 0.3896(10) 0.769(4) 0.026(4) Uiso 1 1 d . . . . .
N8 N 0.37721(4) 0.36111(6) 0.5612(2) 0.02081(17) Uani 1 1 d . . . . .
C9 C 0.32842(4) 0.33247(6) 0.6681(2) 0.01893(17) Uani 1 1 d . . . . .
C10 C 0.27478(4) 0.35329(7) 0.5036(2) 0.02065(19) Uani 1 1 d . . . . .
H10A H 0.2782(6) 0.3303(9) 0.319(4) 0.027(4) Uiso 1 1 d . . . . .
H10B H 0.2708(6) 0.4119(10) 0.475(4) 0.024(4) Uiso 1 1 d . . . . .
N11 N 0.22483(4) 0.32789(5) 0.6516(2) 0.02049(16) Uani 1 1 d . . . . .
C12 C 0.19840(5) 0.38799(6) 0.8326(2) 0.02138(19) Uani 1 1 d . . . . .
H12A H 0.1745(6) 0.3589(9) 0.969(3) 0.016(3) Uiso 1 1 d . . . . .
H12B H 0.2276(7) 0.4141(10) 0.935(4) 0.029(4) Uiso 1 1 d . . . . .
C13 C 0.16676(4) 0.44895(6) 0.6617(3) 0.02099(18) Uani 1 1 d . . . . .
C14 C 0.18562(6) 0.52748(7) 0.6435(3) 0.0311(3) Uani 1 1 d . . . . .
H14 H 0.2216(7) 0.5411(11) 0.737(4) 0.035(4) Uiso 1 1 d . . . . .
C15 C 0.15652(8) 0.58284(8) 0.4794(4) 0.0418(3) Uani 1 1 d . . . . .
H15 H 0.1695(9) 0.6366(14) 0.474(6) 0.057(6) Uiso 1 1 d . . . . .
C16 C 0.10944(7) 0.55941(9) 0.3322(4) 0.0430(4) Uani 1 1 d . . . . .
H16 H 0.0897(9) 0.5980(13) 0.209(6) 0.061(6) Uiso 1 1 d . . . . .
C17 C 0.09027(7) 0.48117(10) 0.3484(4) 0.0402(3) Uani 1 1 d . . . . .
H17 H 0.0558(10) 0.4650(14) 0.253(6) 0.063(7) Uiso 1 1 d . . . . .
C18 C 0.11874(5) 0.42634(8) 0.5139(3) 0.0288(2) Uani 1 1 d . . . . .
H18 H 0.1062(7) 0.3714(11) 0.527(4) 0.034(4) Uiso 1 1 d . . . . .
C19 C 0.37820(5) 0.42269(6) 0.3491(2) 0.02109(18) Uani 1 1 d . . . . .
H19A H 0.4170(7) 0.4263(9) 0.269(4) 0.029(4) Uiso 1 1 d . . . . .
H19B H 0.3550(6) 0.4100(9) 0.198(4) 0.025(4) Uiso 1 1 d . . . . .
C20 C 0.36367(5) 0.50497(6) 0.4689(3) 0.02233(19) Uani 1 1 d . . . . .
O21 O 0.35601(5) 0.51411(6) 0.72156(19) 0.0370(2) Uani 1 1 d . . . . .
N22 N 0.36015(5) 0.56281(6) 0.2819(2) 0.0264(2) Uani 1 1 d . . . . .
H22A H 0.3630(8) 0.5507(12) 0.101(4) 0.037(5) Uiso 1 1 d . . . . .
H22B H 0.3530(7) 0.6144(12) 0.335(4) 0.037(4) Uiso 1 1 d . . . . .
O23 O 0.32615(3) 0.28952(5) 0.87599(19) 0.02318(16) Uani 1 1 d . . . . .
C24 C 0.20854(4) 0.25037(6) 0.6645(2) 0.02129(19) Uani 1 1 d . . . . .
O25 O 0.17041(4) 0.22842(5) 0.8228(2) 0.02799(18) Uani 1 1 d . . . . .
C26 C 0.23738(5) 0.19232(7) 0.4704(3) 0.0274(2) Uani 1 1 d . . . . .
H26A H 0.2304(9) 0.2056(13) 0.276(6) 0.056(6) Uiso 1 1 d . . . . .
H26B H 0.2252(9) 0.1411(14) 0.521(6) 0.057(6) Uiso 1 1 d . . . . .
H26C H 0.2754(10) 0.1925(14) 0.487(6) 0.059(6) 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
C1 C6 1.3910(17) . ?
C1 C2 1.3918(19) . ?
C1 H1 0.998(18) . ?
C2 C3 1.392(2) . ?
C2 H2 0.98(2) . ?
C3 C4 1.380(2) . ?
C3 H3 0.94(2) . ?
C4 C5 1.3885(19) . ?
C4 H4 0.999(19) . ?
C5 C6 1.3931(16) . ?
C5 H5 0.94(2) . ?
C6 C7 1.5107(16) . ?
C7 N8 1.4679(15) . ?
C7 H7A 0.978(19) . ?
C7 H7B 0.947(17) . ?
N8 C9 1.3538(14) . ?
N8 C19 1.4474(15) . ?
C9 O23 1.2288(14) . ?
C9 C10 1.5370(15) . ?
C10 N11 1.4449(14) . ?
C10 H10A 0.969(19) . ?
C10 H10B 0.995(16) . ?
N11 C24 1.3565(14) . ?
N11 C12 1.4689(14) . ?
C12 C13 1.5083(16) . ?
C12 H12A 0.994(15) . ?
C12 H12B 0.955(17) . ?
C13 C14 1.3924(16) . ?
C13 C18 1.3939(17) . ?
C14 C15 1.398(2) . ?
C14 H14 0.989(18) . ?
C15 C16 1.378(3) . ?
C15 H15 0.95(2) . ?
C16 C17 1.390(2) . ?
C16 H16 0.99(2) . ?
C17 C18 1.3885(19) . ?
C17 H17 0.97(2) . ?
C18 H18 0.970(18) . ?
C19 C20 1.5322(15) . ?
C19 H19A 0.999(17) . ?
C19 H19B 0.932(18) . ?
C20 O21 1.2321(15) . ?
C20 N22 1.3217(16) . ?
N22 H22A 0.89(2) . ?
N22 H22B 0.917(19) . ?
C24 O25 1.2360(14) . ?
C24 C26 1.5090(16) . ?
C26 H26A 0.97(3) . ?
C26 H26B 0.94(2) . ?
C26 H26C 0.91(2) . ?

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 C1 C2 120.18(11) . . ?
C6 C1 H1 118.5(10) . . ?
C2 C1 H1 121.3(10) . . ?
C3 C2 C1 120.32(13) . . ?
C3 C2 H2 119.8(13) . . ?
C1 C2 H2 119.8(13) . . ?
C4 C3 C2 119.50(12) . . ?
C4 C3 H3 120.5(12) . . ?
C2 C3 H3 120.0(12) . . ?
C3 C4 C5 120.41(12) . . ?
C3 C4 H4 119.1(12) . . ?
C5 C4 H4 120.4(12) . . ?
C4 C5 C6 120.47(13) . . ?
C4 C5 H5 120.8(11) . . ?
C6 C5 H5 118.7(11) . . ?
C1 C6 C5 119.12(11) . . ?
C1 C6 C7 120.55(10) . . ?
C5 C6 C7 120.33(11) . . ?
N8 C7 C6 111.28(10) . . ?
N8 C7 H7A 107.8(10) . . ?
C6 C7 H7A 112.2(10) . . ?
N8 C7 H7B 110.3(10) . . ?
C6 C7 H7B 109.2(10) . . ?
H7A C7 H7B 106.0(15) . . ?
C9 N8 C19 122.11(9) . . ?
C9 N8 C7 120.08(10) . . ?
C19 N8 C7 116.67(9) . . ?
O23 C9 N8 123.44(10) . . ?
O23 C9 C10 120.73(10) . . ?
N8 C9 C10 115.76(9) . . ?
N11 C10 C9 111.22(9) . . ?
N11 C10 H10A 113.5(9) . . ?
C9 C10 H10A 107.9(9) . . ?
N11 C10 H10B 106.3(9) . . ?
C9 C10 H10B 111.8(9) . . ?
H10A C10 H10B 106.0(14) . . ?
C24 N11 C10 122.56(9) . . ?
C24 N11 C12 120.49(9) . . ?
C10 N11 C12 115.95(9) . . ?
N11 C12 C13 110.92(9) . . ?
N11 C12 H12A 107.2(9) . . ?
C13 C12 H12A 113.9(8) . . ?
N11 C12 H12B 107.8(10) . . ?
C13 C12 H12B 109.2(10) . . ?
H12A C12 H12B 107.6(14) . . ?
C14 C13 C18 119.20(11) . . ?
C14 C13 C12 120.91(11) . . ?
C18 C13 C12 119.87(10) . . ?
C13 C14 C15 120.22(14) . . ?
C13 C14 H14 117.8(11) . . ?
C15 C14 H14 121.8(11) . . ?
C16 C15 C14 119.92(14) . . ?
C16 C15 H15 121.1(15) . . ?
C14 C15 H15 118.9(15) . . ?
C15 C16 C17 120.38(13) . . ?
C15 C16 H16 120.0(13) . . ?
C17 C16 H16 119.5(13) . . ?
C18 C17 C16 119.75(15) . . ?
C18 C17 H17 119.4(14) . . ?
C16 C17 H17 120.8(14) . . ?
C17 C18 C13 120.51(13) . . ?
C17 C18 H18 121.0(11) . . ?
C13 C18 H18 118.5(11) . . ?
N8 C19 C20 112.03(10) . . ?
N8 C19 H19A 109.1(9) . . ?
C20 C19 H19A 107.2(9) . . ?
N8 C19 H19B 111.7(10) . . ?
C20 C19 H19B 111.2(10) . . ?
H19A C19 H19B 105.3(15) . . ?
O21 C20 N22 124.33(11) . . ?
O21 C20 C19 120.81(11) . . ?
N22 C20 C19 114.86(10) . . ?
C20 N22 H22A 119.1(13) . . ?
C20 N22 H22B 121.0(13) . . ?
H22A N22 H22B 119.8(19) . . ?
O25 C24 N11 121.44(10) . . ?
O25 C24 C26 121.18(10) . . ?
N11 C24 C26 117.35(10) . . ?
C24 C26 H26A 111.4(13) . . ?
C24 C26 H26B 106.8(15) . . ?
H26A C26 H26B 114(2) . . ?
C24 C26 H26C 113.3(16) . . ?
H26A C26 H26C 105(2) . . ?
H26B C26 H26C 107(2) . . ?

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
C10 H10A O23 0.969(19) 2.499(19) 3.4126(14) 157.1(12) 1_554
C19 H19B O23 0.932(18) 2.631(17) 3.4099(15) 141.5(13) 1_554
N22 H22A O21 0.89(2) 1.92(2) 2.8040(14) 169.3(18) 1_554
C26 H26A O25 0.97(3) 2.62(3) 3.5346(18) 156.7(17) 1_554
N22 H22B O25 0.917(19) 1.990(19) 2.8743(13) 161.5(19) 4_554

_refine_diff_density_max         0.286
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.037

