# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_shelxs
_database_code_depnum_ccdc_archive 'CCDC 2040420'
loop_
_audit_author_name
_audit_author_address
'Mario Macias'
;Departamento de Quimica, Universidad de los Andes, Bogota
Colombia
;
_audit_update_record             
;
2020-10-24 deposited with the CCDC.	2020-12-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 N O, F6 P'
_chemical_formula_sum            'C18 H18 F6 N O P'
_chemical_formula_weight         409.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_H-M_alt        'P 61'
_space_group_name_Hall           'P 61'

_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, x, z+1/6'
'y, -x+y, z+5/6'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'-x, -y, z+1/2'

_cell_length_a                   9.8217(9)
_cell_length_b                   9.8217(9)
_cell_length_c                   32.600(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2723.4(7)
_cell_formula_units_Z            6
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9257
_cell_measurement_theta_min      4.2520
_cell_measurement_theta_max      22.8130

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_F_000             1260
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.290
_exptl_absorpt_coefficient_mu    0.218
_shelx_estimated_absorpt_T_min   0.928
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.36868
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.3072
_diffrn_reflns_number            32276
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_av_R_equivalents  0.0867
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         3.041
_diffrn_reflns_theta_max         27.090
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4016
_reflns_number_gt                3153
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.965
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.999

_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2015)'
_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)+(0.0946P)²+0.7154P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1212 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(7)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         4016
_refine_ls_number_parameters     300
_refine_ls_number_restraints     100
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0636
_refine_ls_wR_factor_ref         0.1866
_refine_ls_wR_factor_gt          0.1704
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.127
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

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
P1 P 0.84738(19) 0.12861(18) 0.59541(7) 0.0808(6) Uani 1 1 d . . . . .
O1 O 1.2621(5) 0.7888(5) 0.53592(17) 0.0842(13) Uani 1 1 d . . . . .
N1 N 0.5833(6) 0.4973(6) 0.46253(16) 0.0668(11) Uani 1 1 d . . . . .
H1D H 0.500599 0.473585 0.448289 0.080 Uiso 1 1 calc R U . . .
C1 C 1.3824(9) 0.9484(9) 0.5431(3) 0.105(3) Uani 1 1 d . . . . .
H1A H 1.387472 1.012411 0.520261 0.158 Uiso 1 1 calc R U . . .
H1B H 1.481878 0.953132 0.546272 0.158 Uiso 1 1 calc R U . . .
H1C H 1.358485 0.986479 0.567626 0.158 Uiso 1 1 calc R U . . .
C2 C 1.1242(6) 0.7638(6) 0.51990(16) 0.0600(12) Uani 1 1 d . . . . .
C4 C 0.8757(6) 0.5647(6) 0.49279(15) 0.0528(10) Uani 1 1 d . . . . .
F1A F 0.957(2) 0.079(2) 0.5747(5) 0.138(5) Uani 0.611(16) 1 d D U P A 1
F2A F 0.9870(15) 0.2188(18) 0.6309(5) 0.127(4) Uani 0.611(16) 1 d D U P A 1
F3A F 0.7482(16) 0.1795(14) 0.6241(5) 0.130(4) Uani 0.611(16) 1 d D U P A 1
F4A F 0.7235(16) 0.040(2) 0.5662(6) 0.167(6) Uani 0.611(16) 1 d D U P A 1
F5A F 0.935(3) 0.2960(18) 0.5771(6) 0.117(5) Uani 0.611(16) 1 d D U P A 1
F6A F 0.7879(14) -0.0258(13) 0.6255(4) 0.118(3) Uani 0.611(16) 1 d D U P A 1
F1B F 0.771(3) 0.042(3) 0.5495(7) 0.140(6) Uani 0.389(16) 1 d D U P A 2
F2B F 0.910(3) 0.212(3) 0.6338(7) 0.147(8) Uani 0.389(16) 1 d D U P A 2
F3B F 0.7025(18) 0.163(2) 0.5937(10) 0.154(6) Uani 0.389(16) 1 d D U P A 2
F4B F 0.936(4) 0.279(3) 0.5666(10) 0.145(10) Uani 0.389(16) 1 d D U P A 2
F5B F 0.974(3) 0.087(3) 0.5884(8) 0.114(5) Uani 0.389(16) 1 d D U P A 2
F6B F 0.719(3) -0.028(2) 0.6106(8) 0.152(7) Uani 0.389(16) 1 d D U P A 2
C3 C 1.0183(6) 0.6061(6) 0.50962(17) 0.0597(11) Uani 1 1 d . . . . .
H3 H 1.045843 0.529637 0.514349 0.072 Uiso 1 1 calc R U . . .
C5 C 0.8373(6) 0.6826(6) 0.48441(16) 0.0539(10) Uani 1 1 d . . . . .
C6 C 0.9442(7) 0.8397(6) 0.49632(18) 0.0637(13) Uani 1 1 d . . . . .
H6 H 0.917558 0.917402 0.492590 0.076 Uiso 1 1 calc R U . . .
C10 C 0.6915(6) 0.6441(7) 0.46483(17) 0.0611(12) Uani 1 1 d . . . . .
C9 C 0.5934(7) 0.3705(7) 0.48261(19) 0.0696(14) Uani 1 1 d . . . . .
H9A H 0.521319 0.271300 0.469586 0.084 Uiso 1 1 calc R U . . .
H9B H 0.563196 0.364390 0.511170 0.084 Uiso 1 1 calc R U . . .
C8 C 0.7604(7) 0.3983(6) 0.47992(19) 0.0663(13) Uani 1 1 d . . . . .
H8A H 0.770917 0.324887 0.497675 0.080 Uiso 1 1 calc R U . . .
H8B H 0.782491 0.381025 0.452015 0.080 Uiso 1 1 calc R U . . .
C7 C 1.0858(7) 0.8773(6) 0.51321(18) 0.0647(13) Uani 1 1 d . . . . .
H7 H 1.156562 0.981019 0.520186 0.078 Uiso 1 1 calc R U . . .
C12 C 0.5310(6) 0.7599(7) 0.44381(17) 0.0626(13) Uani 1 1 d . . . . .
H12 H 0.444926 0.668083 0.453478 0.075 Uiso 1 1 calc R U . . .
C11 C 0.6689(7) 0.7706(7) 0.44655(19) 0.0678(13) Uani 1 1 d . . . . .
H11 H 0.756406 0.860777 0.436699 0.081 Uiso 1 1 calc R U . . .
C13 C 0.5010(7) 0.8797(6) 0.42688(16) 0.0642(12) Uani 1 1 d . . . . .
C18 C 0.6180(7) 1.0165(7) 0.40715(18) 0.0666(13) Uani 1 1 d . . . . .
H18 H 0.720812 1.036314 0.405468 0.080 Uiso 1 1 calc R U . . .
C17 C 0.5770(8) 1.1213(7) 0.3903(2) 0.0748(16) Uani 1 1 d . . . . .
H17 H 0.651951 1.210561 0.376559 0.090 Uiso 1 1 calc R U . . .
C16 C 0.4266(9) 1.0928(8) 0.3939(2) 0.0776(16) Uani 1 1 d . . . . .
H16 H 0.399884 1.163240 0.382564 0.093 Uiso 1 1 calc R U . . .
C15 C 0.3152(9) 0.9633(9) 0.4138(2) 0.0844(18) Uani 1 1 d . . . . .
H15 H 0.214467 0.948501 0.416635 0.101 Uiso 1 1 calc R U . . .
C14 C 0.3478(8) 0.8554(8) 0.4295(2) 0.0746(15) Uani 1 1 d . . . . .
H14 H 0.268953 0.765354 0.442066 0.089 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 F4A 1.446(12) . ?
P1 F2B 1.45(2) . ?
P1 F6B 1.500(17) . ?
P1 F5B 1.51(2) . ?
P1 F5A 1.544(17) . ?
P1 F1A 1.546(16) . ?
P1 F4B 1.60(3) . ?
P1 F3A 1.600(10) . ?
P1 F3B 1.619(16) . ?
P1 F6A 1.649(10) . ?
P1 F2A 1.671(13) . ?
P1 F1B 1.702(19) . ?
O1 C2 1.355(6) . ?
O1 C1 1.434(8) . ?
N1 C10 1.297(8) . ?
N1 C9 1.454(8) . ?
C2 C7 1.360(8) . ?
C2 C3 1.408(7) . ?
C4 C3 1.363(7) . ?
C4 C5 1.412(7) . ?
C4 C8 1.509(7) . ?
C5 C6 1.419(7) . ?
C5 C10 1.435(7) . ?
C6 C7 1.364(8) . ?
C10 C11 1.491(8) . ?
C9 C8 1.524(8) . ?
C12 C11 1.308(8) . ?
C12 C13 1.457(8) . ?
C13 C14 1.403(9) . ?
C13 C18 1.413(8) . ?
C18 C17 1.393(8) . ?
C17 C16 1.364(9) . ?
C16 C15 1.358(11) . ?
C15 C14 1.352(10) . ?

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
F2B P1 F6B 101.2(14) . . ?
F2B P1 F5B 96.4(15) . . ?
F6B P1 F5B 98.9(15) . . ?
F4A P1 F5A 103.8(11) . . ?
F4A P1 F1A 91.8(9) . . ?
F5A P1 F1A 93.6(11) . . ?
F2B P1 F4B 95.8(16) . . ?
F6B P1 F4B 159.0(19) . . ?
F5B P1 F4B 91.2(16) . . ?
F4A P1 F3A 96.6(9) . . ?
F5A P1 F3A 89.6(8) . . ?
F1A P1 F3A 170.0(8) . . ?
F2B P1 F3B 94.5(13) . . ?
F6B P1 F3B 81.3(12) . . ?
F5B P1 F3B 168.8(13) . . ?
F4B P1 F3B 85.2(17) . . ?
F4A P1 F6A 91.9(9) . . ?
F5A P1 F6A 164.2(10) . . ?
F1A P1 F6A 87.3(9) . . ?
F3A P1 F6A 87.0(6) . . ?
F4A P1 F2A 175.8(10) . . ?
F5A P1 F2A 80.4(10) . . ?
F1A P1 F2A 87.3(8) . . ?
F3A P1 F2A 84.0(7) . . ?
F6A P1 F2A 83.9(7) . . ?
F2B P1 F1B 175.6(16) . . ?
F6B P1 F1B 80.9(12) . . ?
F5B P1 F1B 87.0(11) . . ?
F4B P1 F1B 81.2(15) . . ?
F3B P1 F1B 82.0(11) . . ?
C2 O1 C1 117.7(5) . . ?
C10 N1 C9 123.9(5) . . ?
O1 C2 C7 125.1(5) . . ?
O1 C2 C3 114.4(5) . . ?
C7 C2 C3 120.5(5) . . ?
C3 C4 C5 119.3(5) . . ?
C3 C4 C8 122.6(5) . . ?
C5 C4 C8 118.0(5) . . ?
C4 C3 C2 120.5(5) . . ?
C4 C5 C6 118.9(5) . . ?
C4 C5 C10 120.7(5) . . ?
C6 C5 C10 120.4(4) . . ?
C7 C6 C5 120.3(5) . . ?
N1 C10 C5 118.3(5) . . ?
N1 C10 C11 121.5(5) . . ?
C5 C10 C11 120.2(5) . . ?
N1 C9 C8 110.4(5) . . ?
C4 C8 C9 109.7(4) . . ?
C2 C7 C6 120.4(5) . . ?
C11 C12 C13 125.5(6) . . ?
C12 C11 C10 122.6(6) . . ?
C14 C13 C18 118.8(5) . . ?
C14 C13 C12 118.2(5) . . ?
C18 C13 C12 123.0(5) . . ?
C17 C18 C13 119.0(6) . . ?
C16 C17 C18 119.8(6) . . ?
C15 C16 C17 121.1(6) . . ?
C14 C15 C16 121.3(7) . . ?
C15 C14 C13 119.9(7) . . ?

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 O1 C2 C7 -5.7(10) . . . . ?
C1 O1 C2 C3 173.5(6) . . . . ?
C5 C4 C3 C2 2.2(8) . . . . ?
C8 C4 C3 C2 177.9(5) . . . . ?
O1 C2 C3 C4 -179.3(5) . . . . ?
C7 C2 C3 C4 0.0(9) . . . . ?
C3 C4 C5 C6 -4.2(8) . . . . ?
C8 C4 C5 C6 179.9(5) . . . . ?
C3 C4 C5 C10 176.9(5) . . . . ?
C8 C4 C5 C10 1.0(7) . . . . ?
C4 C5 C6 C7 4.1(8) . . . . ?
C10 C5 C6 C7 -177.0(6) . . . . ?
C9 N1 C10 C5 7.2(8) . . . . ?
C9 N1 C10 C11 -174.8(5) . . . . ?
C4 C5 C10 N1 13.7(8) . . . . ?
C6 C5 C10 N1 -165.2(5) . . . . ?
C4 C5 C10 C11 -164.3(5) . . . . ?
C6 C5 C10 C11 16.7(8) . . . . ?
C10 N1 C9 C8 -39.5(8) . . . . ?
C3 C4 C8 C9 152.2(5) . . . . ?
C5 C4 C8 C9 -32.1(7) . . . . ?
N1 C9 C8 C4 48.6(6) . . . . ?
O1 C2 C7 C6 179.0(6) . . . . ?
C3 C2 C7 C6 -0.2(9) . . . . ?
C5 C6 C7 C2 -1.9(9) . . . . ?
C13 C12 C11 C10 179.1(5) . . . . ?
N1 C10 C11 C12 31.0(9) . . . . ?
C5 C10 C11 C12 -151.1(6) . . . . ?
C11 C12 C13 C14 -174.5(6) . . . . ?
C11 C12 C13 C18 7.1(9) . . . . ?
C14 C13 C18 C17 -1.2(8) . . . . ?
C12 C13 C18 C17 177.2(5) . . . . ?
C13 C18 C17 C16 1.7(9) . . . . ?
C18 C17 C16 C15 0.0(10) . . . . ?
C17 C16 C15 C14 -2.2(11) . . . . ?
C16 C15 C14 C13 2.6(10) . . . . ?
C18 C13 C14 C15 -0.9(9) . . . . ?
C12 C13 C14 C15 -179.3(6) . . . . ?

_refine_diff_density_max         0.321
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.048



####################################################################### 
# 
# 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_shelxs_sq_sq
_database_code_depnum_ccdc_archive 'CCDC 2040421'
loop_
_audit_author_name
_audit_author_address
'Mario Macias'
;Departamento de Quimica, Universidad de los Andes, Bogota
Colombia
;
_audit_update_record             
;
2020-10-24 deposited with the CCDC.	2020-12-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H23 N O3'
_chemical_formula_weight         325.39

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

_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'

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

_cell_length_a                   11.8343(16)
_cell_length_b                   12.4529(11)
_cell_length_c                   14.8774(18)
_cell_angle_alpha                90
_cell_angle_beta                 106.205(13)
_cell_angle_gamma                90
_cell_volume                     2105.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6366
_cell_measurement_theta_min      3.3200
_cell_measurement_theta_max      26.7230

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            translucent
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.027
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.069
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.88164
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.3072
_diffrn_reflns_number            24600
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.272
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4619
_reflns_number_gt                3110
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2015)'
_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)+(0.0900P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4619
_refine_ls_number_parameters     221
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.0852
_refine_ls_wR_factor_ref         0.2637
_refine_ls_wR_factor_gt          0.2501
_refine_ls_goodness_of_fit_ref   1.757
_refine_ls_restrained_S_all      1.924
_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 -0.1067(3) 0.6792(2) -0.21266(19) 0.0811(8) Uani 1 1 d . . . . .
H1A H -0.079580 0.657186 -0.264895 0.122 Uiso 1 1 calc R U . . .
H1B H -0.136909 0.751119 -0.222814 0.122 Uiso 1 1 calc R U . . .
H1C H -0.167838 0.631637 -0.206377 0.122 Uiso 1 1 calc R U . . .
O1 O -0.01150(16) 0.67599(11) -0.12951(11) 0.0691(5) Uani 1 1 d . . . . .
N1 N 0.1756(2) 0.20481(15) -0.02330(15) 0.0724(6) Uani 1 1 d . . . . .
C3 C 0.0082(2) 0.48386(17) -0.14759(15) 0.0613(6) Uani 1 1 d . . . . .
H3 H -0.054638 0.481358 -0.201536 0.074 Uiso 1 1 calc R U . . .
O3 O 0.8750(2) 0.3608(2) 0.3131(2) 0.1271(7) Uani 1 1 d . U . . .
C19 C 0.9093(5) 0.4540(4) 0.3700(3) 0.1492(14) Uani 1 1 d . U . . .
H19A H 0.932370 0.509536 0.334043 0.224 Uiso 1 1 calc R U . . .
H19B H 0.974323 0.436548 0.423005 0.224 Uiso 1 1 calc R U . . .
H19C H 0.844310 0.478498 0.391332 0.224 Uiso 1 1 calc R U . . .
C2 C 0.0418(2) 0.58141(16) -0.10328(14) 0.0571(6) Uani 1 1 d . . . . .
O2 O 0.16267(16) 0.68640(12) 0.01254(11) 0.0702(5) Uani 1 1 d . . . . .
C5 C 0.1643(2) 0.39583(17) -0.03218(15) 0.0582(6) Uani 1 1 d . . . . .
C4 C 0.0669(2) 0.39038(17) -0.11263(15) 0.0580(6) Uani 1 1 d . . . . .
C6 C 0.1986(2) 0.49475(16) 0.01109(16) 0.0607(6) Uani 1 1 d . . . . .
H6 H 0.262551 0.498329 0.064203 0.073 Uiso 1 1 calc R U . . .
C7 C 0.1387(2) 0.58653(16) -0.02417(15) 0.0574(6) Uani 1 1 d . . . . .
C8 C 0.0358(3) 0.28389(17) -0.15956(18) 0.0731(7) Uani 1 1 d . . . . .
H8A H 0.082056 0.272227 -0.203222 0.088 Uiso 1 1 calc R U . . .
H8B H -0.046679 0.283547 -0.194624 0.088 Uiso 1 1 calc R U . . .
C9 C 0.0592(3) 0.19434(19) -0.0880(2) 0.0774(8) Uani 1 1 d . . . . .
H9A H 0.000660 0.196490 -0.053574 0.093 Uiso 1 1 calc R U . . .
H9B H 0.052747 0.125617 -0.119706 0.093 Uiso 1 1 calc R U . . .
C14 C 0.5829(3) 0.4319(2) 0.1628(2) 0.0913(9) Uani 1 1 d . . . . .
H14 H 0.528280 0.487205 0.155444 0.110 Uiso 1 1 calc R U . . .
C13 C 0.5561(3) 0.3433(2) 0.1038(2) 0.0744(7) Uani 1 1 d . . . . .
C12 C 0.4402(3) 0.3340(3) 0.0309(2) 0.0844(8) Uani 1 1 d . . . . .
H12A H 0.446955 0.282729 -0.016435 0.101 Uiso 1 1 calc R U . . .
H12B H 0.419051 0.403019 0.000689 0.101 Uiso 1 1 calc R U . . .
C11 C 0.3439(3) 0.29742(19) 0.07438(19) 0.0706(7) Uani 1 1 d . . . . .
H11A H 0.361883 0.225649 0.099650 0.085 Uiso 1 1 calc R U . . .
H11B H 0.342540 0.344973 0.125714 0.085 Uiso 1 1 calc R U . . .
C10 C 0.2246(2) 0.29712(18) 0.00441(17) 0.0637(6) Uani 1 1 d . . . . .
C18 C 0.6407(3) 0.2627(2) 0.1193(2) 0.0813(8) Uani 1 1 d . . . . .
H18 H 0.626627 0.201547 0.081937 0.098 Uiso 1 1 calc R U . . .
C17 C 0.7447(3) 0.2719(2) 0.1887(2) 0.0871(8) Uani 1 1 d . . . . .
H17 H 0.800209 0.217119 0.197614 0.105 Uiso 1 1 calc R U . . .
C16 C 0.7675(3) 0.3607(3) 0.2447(3) 0.0973(7) Uani 1 1 d . U . . .
C15 C 0.6885(3) 0.4403(3) 0.2321(3) 0.0968(7) Uani 1 1 d . U . . .
H15 H 0.704497 0.501065 0.269801 0.116 Uiso 1 1 calc R U . . .
C20 C 0.2637(3) 0.6988(2) 0.0903(2) 0.0957(11) Uani 1 1 d . . . . .
H20A H 0.332217 0.675470 0.073241 0.144 Uiso 1 1 calc R U . . .
H20B H 0.254652 0.656411 0.141688 0.144 Uiso 1 1 calc R U . . .
H20C H 0.272368 0.773048 0.108355 0.144 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.422(3) . ?
O1 C2 1.342(2) . ?
N1 C10 1.302(3) . ?
N1 C9 1.449(3) . ?
C3 C4 1.381(3) . ?
C3 C2 1.386(3) . ?
O3 C16 1.390(4) . ?
O3 C19 1.427(5) . ?
C2 C7 1.397(3) . ?
O2 C7 1.356(3) . ?
O2 C20 1.421(3) . ?
C5 C6 1.397(3) . ?
C5 C4 1.413(3) . ?
C5 C10 1.449(3) . ?
C4 C8 1.496(3) . ?
C6 C7 1.370(3) . ?
C8 C9 1.513(4) . ?
C14 C15 1.384(5) . ?
C14 C13 1.390(4) . ?
C13 C18 1.391(4) . ?
C13 C12 1.497(4) . ?
C12 C11 1.529(4) . ?
C11 C10 1.501(4) . ?
C18 C17 1.373(4) . ?
C17 C16 1.366(4) . ?
C16 C15 1.339(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
C2 O1 C1 118.16(18) . . ?
C10 N1 C9 123.1(2) . . ?
C4 C3 C2 120.8(2) . . ?
C16 O3 C19 119.1(3) . . ?
O1 C2 C3 125.6(2) . . ?
O1 C2 C7 114.45(18) . . ?
C3 C2 C7 119.98(19) . . ?
C7 O2 C20 117.49(18) . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 C10 121.7(2) . . ?
C4 C5 C10 118.5(2) . . ?
C3 C4 C5 118.97(19) . . ?
C3 C4 C8 122.6(2) . . ?
C5 C4 C8 118.3(2) . . ?
C7 C6 C5 120.4(2) . . ?
O2 C7 C6 125.7(2) . . ?
O2 C7 C2 114.28(18) . . ?
C6 C7 C2 120.01(19) . . ?
C4 C8 C9 110.6(2) . . ?
N1 C9 C8 110.8(2) . . ?
C15 C14 C13 122.0(3) . . ?
C14 C13 C18 116.2(3) . . ?
C14 C13 C12 121.4(3) . . ?
C18 C13 C12 122.4(3) . . ?
C13 C12 C11 110.9(2) . . ?
C10 C11 C12 112.0(2) . . ?
N1 C10 C5 120.1(2) . . ?
N1 C10 C11 118.1(2) . . ?
C5 C10 C11 121.8(2) . . ?
C17 C18 C13 121.2(3) . . ?
C16 C17 C18 120.6(3) . . ?
C15 C16 C17 120.1(3) . . ?
C15 C16 O3 124.3(3) . . ?
C17 C16 O3 115.6(3) . . ?
C16 C15 C14 119.9(3) . . ?

_refine_diff_density_max         0.498
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.075




