# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_123
_audit_block_doi                 10.5517/ccdc.csd.cc2827p9
_database_code_depnum_ccdc_archive 'CCDC 2087530'
loop_
_audit_author_name
_audit_author_address
'Ju WU'
;Ningbo University
China
;
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2021-12-03 downloaded from the CCDC.
;
_audit_creation_date             2021-04-01
_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         '0.16(C20 H22 N O5 P)'
_chemical_formula_sum            'C H N O P'
_chemical_formula_weight         74.00
_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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.4032(2)
_cell_length_b                   12.0627(4)
_cell_length_c                   19.3355(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.8190(10)
_cell_angle_gamma                90
_cell_volume                     1949.85(10)
_cell_formula_units_Z            25
_cell_measurement_reflns_used    9842
_cell_measurement_temperature    303(2)
_cell_measurement_theta_max      71.89
_cell_measurement_theta_min      4.33
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.702
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6780
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1037 before and 0.0676 after correction.
The Ratio of minimum to maximum transmission is 0.8997.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             925
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            43223
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.263
_diffrn_reflns_theta_min         4.326
_diffrn_ambient_temperature      303.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3223
_reflns_number_total             3836
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3836
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0491
_refine_ls_restrained_S_all      1.069
_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)+(0.0805P)²+0.4923P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1479
_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 Secondary CH2 refined with riding coordinates:
 C00O(H00H,H00N), C00P(H00O,H00P)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00F(H00F), C00G(H00G), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M)
2.c Idealised Me refined as rotating group:
 C00N(H00A,H00B,H00E), C00Q(H00Q,H00R,H00S), C00R(H00T,H00U,H00V)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
P001 P 0.20365(6) 0.34348(4) 0.39728(2) 0.05777(19) Uani 1 1 d . . . . .
O002 O 0.09667(19) 0.38910(15) 0.34048(8) 0.0752(5) Uani 1 1 d . . . . .
O003 O 0.4641(2) 0.16766(15) 0.47359(7) 0.0773(5) Uani 1 1 d . . . . .
O004 O 0.1182(2) 0.25935(16) 0.44260(8) 0.0799(5) Uani 1 1 d . . . . .
O005 O 0.2861(3) 0.42784(15) 0.45079(9) 0.0893(6) Uani 1 1 d . . . . .
N006 N 0.5823(2) 0.15213(16) 0.37268(9) 0.0648(5) Uani 1 1 d . . . . .
O007 O 0.8748(2) 0.1364(2) 0.15302(10) 0.0933(6) Uani 1 1 d . . . . .
C008 C 0.3686(2) 0.26919(15) 0.36772(9) 0.0500(4) Uani 1 1 d . . . . .
C009 C 0.4201(2) 0.27295(15) 0.30470(9) 0.0486(4) Uani 1 1 d . . . . .
C00A C 0.3559(2) 0.33613(16) 0.24210(9) 0.0514(4) Uani 1 1 d . . . . .
C00B C 0.5677(2) 0.19913(17) 0.30256(10) 0.0547(4) Uani 1 1 d . . . . .
C00C C 0.5396(2) 0.10898(16) 0.24919(10) 0.0561(4) Uani 1 1 d . . . . .
H00C H 0.450401 0.063668 0.250365 0.067 Uiso 1 1 calc R . . . .
C00D C 0.6368(2) 0.09134(18) 0.20047(11) 0.0604(5) Uani 1 1 d . . . . .
H00D H 0.612987 0.034546 0.168565 0.073 Uiso 1 1 calc R . . . .
C00E C 0.4730(3) 0.19209(17) 0.41284(10) 0.0587(5) Uani 1 1 d . . . . .
C00F C 0.2401(3) 0.2897(2) 0.19486(11) 0.0658(5) Uani 1 1 d . . . . .
H00F H 0.203118 0.218456 0.202404 0.079 Uiso 1 1 calc R . . . .
C00G C 0.7134(2) 0.26837(19) 0.29323(12) 0.0669(6) Uani 1 1 d . . . . .
H00G H 0.736673 0.327609 0.323345 0.080 Uiso 1 1 calc R . . . .
C00H C 0.7804(3) 0.1582(2) 0.19516(11) 0.0652(5) Uani 1 1 d . . . . .
C00I C 0.8091(3) 0.2496(2) 0.24487(13) 0.0695(6) Uani 1 1 d . . . . .
H00I H 0.897309 0.295357 0.242102 0.083 Uiso 1 1 calc R . . . .
C00J C 0.4100(3) 0.44214(19) 0.23025(14) 0.0731(6) Uani 1 1 d . . . . .
H00J H 0.486480 0.475161 0.261837 0.088 Uiso 1 1 calc R . . . .
C00K C 0.3492(4) 0.4989(2) 0.17077(16) 0.0942(9) Uani 1 1 d . . . . .
H00K H 0.386813 0.569608 0.162184 0.113 Uiso 1 1 calc R . . . .
C00L C 0.1789(3) 0.3479(3) 0.13661(12) 0.0842(8) Uani 1 1 d . . . . .
H00L H 0.099979 0.316136 0.105646 0.101 Uiso 1 1 calc R . . . .
C00M C 0.2335(4) 0.4511(3) 0.12437(14) 0.0920(9) Uani 1 1 d . . . . .
H00M H 0.192955 0.489665 0.084787 0.110 Uiso 1 1 calc R . . . .
C00N C 0.7032(4) 0.0709(3) 0.39638(15) 0.0972(9) Uani 1 1 d . . . . .
H00A H 0.692701 0.007056 0.366590 0.146 Uiso 1 1 calc GR . . . .
H00B H 0.689174 0.049096 0.443138 0.146 Uiso 1 1 calc GR . . . .
H00E H 0.807535 0.102683 0.395089 0.146 Uiso 1 1 calc GR . . . .
C00O C 0.2903(5) 0.5451(3) 0.4443(2) 0.1080(10) Uani 1 1 d . . . . .
H00H H 0.204367 0.569495 0.410473 0.130 Uiso 1 1 calc R . . . .
H00N H 0.391049 0.567674 0.428241 0.130 Uiso 1 1 calc R . . . .
C00P C 0.1413(5) 0.2561(3) 0.51811(15) 0.1058(10) Uani 1 1 d . . . . .
H00O H 0.254452 0.249714 0.533369 0.127 Uiso 1 1 calc R . . . .
H00P H 0.102456 0.324495 0.536744 0.127 Uiso 1 1 calc R . . . .
C00Q C 0.2731(6) 0.5951(3) 0.5104(2) 0.1428(18) Uani 1 1 d . . . . .
H00Q H 0.282883 0.674155 0.506584 0.214 Uiso 1 1 calc GR . . . .
H00R H 0.354917 0.567692 0.544286 0.214 Uiso 1 1 calc GR . . . .
H00S H 0.169853 0.577134 0.524445 0.214 Uiso 1 1 calc GR . . . .
C00R C 0.0591(5) 0.1659(4) 0.54342(19) 0.1290(14) Uani 1 1 d . . . . .
H00T H 0.084697 0.099685 0.519306 0.194 Uiso 1 1 calc GR . . . .
H00U H -0.053979 0.179149 0.536020 0.194 Uiso 1 1 calc GR . . . .
H00V H 0.090408 0.157094 0.592254 0.194 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
P001 O002 1.4550(15) . ?
P001 O004 1.5624(18) . ?
P001 O005 1.5623(17) . ?
P001 C008 1.7920(19) . ?
O003 C00E 1.221(3) . ?
O004 C00P 1.454(3) . ?
O005 C00O 1.421(4) . ?
N006 C00B 1.463(3) . ?
N006 C00E 1.351(3) . ?
N006 C00N 1.452(3) . ?
O007 C00H 1.222(3) . ?
C008 C009 1.335(3) . ?
C008 C00E 1.497(3) . ?
C009 C00A 1.485(2) . ?
C009 C00B 1.531(3) . ?
C00A C00F 1.384(3) . ?
C00A C00J 1.384(3) . ?
C00B C00C 1.501(3) . ?
C00B C00G 1.508(3) . ?
C00C C00D 1.325(3) . ?
C00D C00H 1.464(3) . ?
C00F C00L 1.382(3) . ?
C00G C00I 1.314(3) . ?
C00H C00I 1.466(3) . ?
C00J C00K 1.390(4) . ?
C00K C00M 1.381(5) . ?
C00L C00M 1.356(5) . ?
C00O C00Q 1.433(5) . ?
C00P C00R 1.403(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
O002 P001 O004 112.65(11) . . ?
O002 P001 O005 116.88(11) . . ?
O002 P001 C008 112.77(9) . . ?
O004 P001 C008 105.57(10) . . ?
O005 P001 O004 104.47(10) . . ?
O005 P001 C008 103.38(10) . . ?
C00P O004 P001 124.0(2) . . ?
C00O O005 P001 127.1(2) . . ?
C00E N006 C00B 113.35(16) . . ?
C00E N006 C00N 123.7(2) . . ?
C00N N006 C00B 123.0(2) . . ?
C009 C008 P001 127.40(14) . . ?
C009 C008 C00E 109.14(17) . . ?
C00E C008 P001 123.46(14) . . ?
C008 C009 C00A 129.56(17) . . ?
C008 C009 C00B 110.11(16) . . ?
C00A C009 C00B 120.33(16) . . ?
C00F C00A C009 120.21(18) . . ?
C00F C00A C00J 119.1(2) . . ?
C00J C00A C009 120.73(19) . . ?
N006 C00B C009 101.10(15) . . ?
N006 C00B C00C 110.42(17) . . ?
N006 C00B C00G 109.42(16) . . ?
C00C C00B C009 111.64(15) . . ?
C00C C00B C00G 113.07(17) . . ?
C00G C00B C009 110.53(17) . . ?
C00D C00C C00B 122.67(18) . . ?
C00C C00D C00H 122.22(19) . . ?
O003 C00E N006 125.4(2) . . ?
O003 C00E C008 128.4(2) . . ?
N006 C00E C008 106.22(16) . . ?
C00L C00F C00A 120.7(2) . . ?
C00I C00G C00B 123.6(2) . . ?
O007 C00H C00D 121.6(2) . . ?
O007 C00H C00I 121.6(2) . . ?
C00D C00H C00I 116.77(19) . . ?
C00G C00I C00H 121.6(2) . . ?
C00A C00J C00K 119.5(3) . . ?
C00M C00K C00J 120.5(3) . . ?
C00M C00L C00F 120.3(3) . . ?
C00L C00M C00K 119.9(2) . . ?
O005 C00O C00Q 109.6(3) . . ?
C00R C00P O004 110.6(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_audit_block_doi                 10.5517/ccdc.csd.cc2827qb
_database_code_depnum_ccdc_archive 'CCDC 2087531'
loop_
_audit_author_name
_audit_author_address
'Ju WU'
;Ningbo University
China
;
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2021-12-03 downloaded from the CCDC.
;
_audit_creation_date             2021-04-13
_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         '0.24(C17 H12 F3 N O2)'
_chemical_formula_sum            'C H F N O P'
_chemical_formula_weight         93.00
_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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   14.1738(8)
_cell_length_b                   6.7235(4)
_cell_length_c                   15.9099(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.003(3)
_cell_angle_gamma                90
_cell_volume                     1488.30(14)
_cell_formula_units_Z            17
_cell_measurement_reflns_used    9109
_cell_measurement_temperature    208(2)
_cell_measurement_theta_max      68.49
_cell_measurement_theta_min      3.18
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.649
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5386
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1401 before and 0.0792 after correction.
The Ratio of minimum to maximum transmission is 0.7152.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.764
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             782
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1247
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25179
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.514
_diffrn_reflns_theta_min         3.176
_diffrn_ambient_temperature      208.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.973
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2126
_reflns_number_total             2779
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2779
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.070
_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)+(0.0758P)²+0.1033P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1379
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00J(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M), C00N(H00N)
2.b Idealised Me refined as rotating group:
 C00H(H00A,H00B,H00G)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F001 F 0.46521(9) 0.4412(2) 0.90755(8) 0.0666(4) Uani 1 1 d . . . . .
O002 O 0.47259(9) 0.6192(2) 0.71774(9) 0.0505(4) Uani 1 1 d . . . . .
F003 F 0.31835(10) 0.4762(3) 0.91877(8) 0.0830(6) Uani 1 1 d . . . . .
F004 F 0.39398(12) 0.7155(3) 0.87320(10) 0.0808(5) Uani 1 1 d . . . . .
O005 O 0.11195(10) -0.1812(2) 0.53814(10) 0.0578(4) Uani 1 1 d . . . . .
N006 N 0.35976(9) 0.4117(2) 0.63996(9) 0.0368(4) Uani 1 1 d . . . . .
C007 C 0.28156(11) 0.3185(3) 0.74980(10) 0.0339(4) Uani 1 1 d . . . . .
C008 C 0.28588(10) 0.2724(3) 0.65561(10) 0.0323(4) Uani 1 1 d . . . . .
C009 C 0.40508(11) 0.5055(3) 0.71206(11) 0.0375(4) Uani 1 1 d . . . . .
C00A C 0.16523(12) -0.0437(3) 0.56795(11) 0.0394(4) Uani 1 1 d . . . . .
C00B C 0.35163(11) 0.4452(3) 0.78027(10) 0.0366(4) Uani 1 1 d . . . . .
C00C C 0.18984(11) 0.3111(3) 0.59854(10) 0.0362(4) Uani 1 1 d . . . . .
H00C H 0.168445 0.443044 0.589422 0.043 Uiso 1 1 calc R . . . .
C00D C 0.32000(11) 0.0616(3) 0.65193(10) 0.0362(4) Uani 1 1 d . . . . .
H00D H 0.383228 0.030294 0.678739 0.043 Uiso 1 1 calc R . . . .
C00E C 0.26433(12) -0.0824(3) 0.61226(11) 0.0399(4) Uani 1 1 d . . . . .
H00E H 0.288990 -0.212285 0.612580 0.048 Uiso 1 1 calc R . . . .
C00F C 0.13432(11) 0.1646(3) 0.56064(11) 0.0396(4) Uani 1 1 d . . . . .
H00F H 0.073473 0.195664 0.528221 0.047 Uiso 1 1 calc R . . . .
C00G C 0.20731(12) 0.2253(3) 0.79115(10) 0.0402(4) Uani 1 1 d . . . . .
C00H C 0.39167(13) 0.4240(3) 0.55855(12) 0.0483(5) Uani 1 1 d . . . . .
H00A H 0.416766 0.296011 0.545254 0.072 Uiso 1 1 calc GR . . . .
H00B H 0.441686 0.523897 0.562257 0.072 Uiso 1 1 calc GR . . . .
H00G H 0.337857 0.460393 0.513816 0.072 Uiso 1 1 calc GR . . . .
C00I C 0.38157(13) 0.5185(4) 0.86976(12) 0.0476(5) Uani 1 1 d . . . . .
C00J C 0.12353(15) 0.3268(5) 0.79441(15) 0.0665(7) Uani 1 1 d . . . . .
H00J H 0.113488 0.454745 0.770548 0.080 Uiso 1 1 calc R . . . .
C00K C 0.22013(19) 0.0367(4) 0.82524(15) 0.0628(6) Uani 1 1 d . . . . .
H00K H 0.276252 -0.034968 0.821992 0.075 Uiso 1 1 calc R . . . .
C00L C 0.0680(2) 0.0531(7) 0.86768(17) 0.0956(13) Uani 1 1 d . . . . .
H00L H 0.020612 -0.005201 0.893775 0.115 Uiso 1 1 calc R . . . .
C00M C 0.1499(3) -0.0478(5) 0.86455(19) 0.0890(10) Uani 1 1 d . . . . .
H00M H 0.159388 -0.175228 0.888958 0.107 Uiso 1 1 calc R . . . .
C00N C 0.05385(17) 0.2387(7) 0.83325(18) 0.0912(12) Uani 1 1 d . . . . .
H00N H -0.003235 0.307769 0.835709 0.109 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C00I 1.328(2) . ?
O002 C009 1.215(2) . ?
F003 C00I 1.326(2) . ?
F004 C00I 1.336(3) . ?
O005 C00A 1.230(2) . ?
N006 C008 1.461(2) . ?
N006 C009 1.358(2) . ?
N006 C00H 1.454(2) . ?
C007 C008 1.543(2) . ?
C007 C00B 1.328(3) . ?
C007 C00G 1.482(2) . ?
C008 C00C 1.508(2) . ?
C008 C00D 1.502(3) . ?
C009 C00B 1.493(2) . ?
C00A C00E 1.470(2) . ?
C00A C00F 1.465(3) . ?
C00B C00I 1.490(3) . ?
C00C C00F 1.331(3) . ?
C00D C00E 1.330(3) . ?
C00G C00J 1.379(3) . ?
C00G C00K 1.377(3) . ?
C00J C00N 1.393(4) . ?
C00K C00M 1.394(4) . ?
C00L C00M 1.353(5) . ?
C00L C00N 1.362(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
C009 N006 C008 113.11(13) . . ?
C009 N006 C00H 123.28(15) . . ?
C00H N006 C008 122.90(15) . . ?
C00B C007 C008 108.54(14) . . ?
C00B C007 C00G 130.85(16) . . ?
C00G C007 C008 120.61(15) . . ?
N006 C008 C007 101.49(13) . . ?
N006 C008 C00C 112.40(14) . . ?
N006 C008 C00D 110.59(13) . . ?
C00C C008 C007 110.59(12) . . ?
C00D C008 C007 107.46(14) . . ?
C00D C008 C00C 113.54(15) . . ?
O002 C009 N006 126.44(16) . . ?
O002 C009 C00B 128.21(17) . . ?
N006 C009 C00B 105.31(14) . . ?
O005 C00A C00E 120.78(19) . . ?
O005 C00A C00F 122.38(17) . . ?
C00F C00A C00E 116.84(16) . . ?
C007 C00B C009 110.89(15) . . ?
C007 C00B C00I 128.16(17) . . ?
C00I C00B C009 120.89(16) . . ?
C00F C00C C008 122.22(18) . . ?
C00E C00D C008 122.64(15) . . ?
C00D C00E C00A 121.64(18) . . ?
C00C C00F C00A 121.95(16) . . ?
C00J C00G C007 119.8(2) . . ?
C00K C00G C007 120.82(18) . . ?
C00K C00G C00J 119.4(2) . . ?
F001 C00I F004 105.66(17) . . ?
F001 C00I C00B 111.72(17) . . ?
F003 C00I F001 107.15(18) . . ?
F003 C00I F004 106.68(18) . . ?
F003 C00I C00B 112.95(16) . . ?
F004 C00I C00B 112.22(18) . . ?
C00G C00J C00N 119.7(3) . . ?
C00G C00K C00M 120.0(3) . . ?
C00M C00L C00N 120.4(2) . . ?
C00L C00M C00K 120.2(3) . . ?
C00L C00N C00J 120.4(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
