# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2121510'
loop_
_audit_author_name
_audit_author_address
a
;CCNU
China
;
_audit_update_record             
;
2021-11-11 deposited with the CCDC.	2022-04-12 downloaded from the CCDC.
;
_audit_creation_date             2021-07-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H17 N2 O P'
_chemical_formula_sum            'C14 H17 N2 O P'
_chemical_formula_weight         260.26
_chemical_absolute_configuration R
_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 0.0033 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'
P P 0.1023 0.0942 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   7.2488(9)
_cell_length_b                   10.7508(14)
_cell_length_c                   17.638(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1374.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      31.73
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.5618
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1673 before and 0.0581 after correction.
The Ratio of minimum to maximum transmission is 0.7528.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_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  0.0347
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12443
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.498
_diffrn_reflns_theta_min         2.219
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3299
_reflns_number_total             3496
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details 
;
 Flack x determined using 1363 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         3496
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0339
_refine_ls_restrained_S_all      1.094
_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)+(0.0447P)²+0.1919P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0887
_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:
 C007(H007), C008(H008), C009(H009), C00B(H00B), C00C(H00C), C00D(H00D),
 C00E(H00E), C00F(H00F)
2.b Idealised Me refined as rotating group:
 C00G(H00A,H00G,H00H), C00H(H00I,H00J,H00K), C00I(H00L,H00M,H00N)
;
_atom_sites_solution_hydrogens   geom
_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
P001 P 0.29634(6) 0.41425(4) 0.33915(3) 0.03166(12) Uani 1 1 d . . . . .
O002 O 0.2969(2) 0.27622(12) 0.34161(9) 0.0461(3) Uani 1 1 d . . . . .
N003 N 0.1662(3) 0.58987(18) 0.23905(9) 0.0459(4) Uani 1 1 d . . . . .
C004 C 0.1670(3) 0.48058(18) 0.41730(10) 0.0348(4) Uani 1 1 d . . . . .
C005 C 0.1825(3) 0.46693(18) 0.25264(10) 0.0345(4) Uani 1 1 d . . . . .
N006 N 0.0193(3) 0.4125(3) 0.14009(11) 0.0641(6) Uani 1 1 d . . . . .
C007 C 0.1060(3) 0.6034(2) 0.41927(11) 0.0431(4) Uani 1 1 d . . . . .
H007 H 0.132449 0.656570 0.379144 0.052 Uiso 1 1 calc R U . . .
C008 C 0.1257(3) 0.4018(2) 0.47776(11) 0.0446(4) Uani 1 1 d . . . . .
H008 H 0.165655 0.319633 0.476931 0.054 Uiso 1 1 calc R U . . .
C009 C 0.1128(3) 0.3799(2) 0.20310(12) 0.0472(5) Uani 1 1 d . . . . .
H009 H 0.130829 0.295944 0.213412 0.057 Uiso 1 1 calc R U . . .
C00A C 0.5304(2) 0.47881(18) 0.34021(12) 0.0376(4) Uani 1 1 d . . . . .
C00B C 0.0059(4) 0.6466(2) 0.48090(12) 0.0539(6) Uani 1 1 d . . . . .
H00B H -0.034619 0.728627 0.481991 0.065 Uiso 1 1 calc R U . . .
C00C C 0.0247(4) 0.4458(3) 0.53943(12) 0.0543(6) Uani 1 1 d . . . . .
H00C H -0.003059 0.392853 0.579547 0.065 Uiso 1 1 calc R U . . .
C00D C 0.0755(4) 0.6207(3) 0.17639(12) 0.0538(6) Uani 1 1 d . . . . .
H00D H 0.061893 0.704455 0.164422 0.065 Uiso 1 1 calc R U . . .
C00E C -0.0339(4) 0.5675(3) 0.54095(12) 0.0568(6) Uani 1 1 d . . . . .
H00E H -0.100374 0.596950 0.582339 0.068 Uiso 1 1 calc R U . . .
C00F C 0.0011(4) 0.5330(3) 0.12864(13) 0.0616(7) Uani 1 1 d . . . . .
H00F H -0.064786 0.559874 0.086466 0.074 Uiso 1 1 calc R U . . .
C00G C 0.6287(4) 0.4165(4) 0.40630(16) 0.0744(9) Uani 1 1 d . . . . .
H00A H 0.567465 0.437766 0.452798 0.112 Uiso 1 1 calc R U . . .
H00G H 0.754327 0.444513 0.408242 0.112 Uiso 1 1 calc R U . . .
H00H H 0.626197 0.327906 0.399570 0.112 Uiso 1 1 calc R U . . .
C00H C 0.6259(4) 0.4425(4) 0.26646(16) 0.0781(10) Uani 1 1 d . . . . .
H00I H 0.619555 0.353982 0.260000 0.117 Uiso 1 1 calc R U . . .
H00J H 0.752685 0.468098 0.268253 0.117 Uiso 1 1 calc R U . . .
H00K H 0.565467 0.482714 0.224661 0.117 Uiso 1 1 calc R U . . .
C00I C 0.5366(4) 0.6192(3) 0.3495(2) 0.0743(8) Uani 1 1 d . . . . .
H00L H 0.476359 0.657923 0.307117 0.112 Uiso 1 1 calc R U . . .
H00M H 0.662703 0.646288 0.351665 0.112 Uiso 1 1 calc R U . . .
H00N H 0.474637 0.642276 0.395482 0.112 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
P001 O002 1.4846(13) . ?
P001 C004 1.813(2) . ?
P001 C005 1.8247(19) . ?
P001 C00A 1.8334(19) . ?
N003 C005 1.348(3) . ?
N003 C00D 1.328(3) . ?
C004 C007 1.393(3) . ?
C004 C008 1.394(3) . ?
C005 C009 1.376(3) . ?
N006 C009 1.348(3) . ?
N006 C00F 1.318(4) . ?
C007 H007 0.9300 . ?
C007 C00B 1.387(3) . ?
C008 H008 0.9300 . ?
C008 C00C 1.394(3) . ?
C009 H009 0.9300 . ?
C00A C00G 1.521(3) . ?
C00A C00H 1.524(3) . ?
C00A C00I 1.519(3) . ?
C00B H00B 0.9300 . ?
C00B C00E 1.388(3) . ?
C00C H00C 0.9300 . ?
C00C C00E 1.377(4) . ?
C00D H00D 0.9300 . ?
C00D C00F 1.374(4) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00G H00A 0.9600 . ?
C00G H00G 0.9600 . ?
C00G H00H 0.9600 . ?
C00H H00I 0.9600 . ?
C00H H00J 0.9600 . ?
C00H H00K 0.9600 . ?
C00I H00L 0.9600 . ?
C00I H00M 0.9600 . ?
C00I H00N 0.9600 . ?

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 C004 111.85(9) . . ?
O002 P001 C005 109.63(9) . . ?
O002 P001 C00A 112.07(9) . . ?
C004 P001 C005 106.25(8) . . ?
C004 P001 C00A 108.78(9) . . ?
C005 P001 C00A 108.02(9) . . ?
C00D N003 C005 115.87(19) . . ?
C007 C004 P001 123.77(14) . . ?
C007 C004 C008 119.25(18) . . ?
C008 C004 P001 116.98(16) . . ?
N003 C005 P001 119.52(14) . . ?
N003 C005 C009 121.40(18) . . ?
C009 C005 P001 119.07(16) . . ?
C00F N006 C009 115.6(2) . . ?
C004 C007 H007 119.9 . . ?
C00B C007 C004 120.20(19) . . ?
C00B C007 H007 119.9 . . ?
C004 C008 H008 119.9 . . ?
C00C C008 C004 120.3(2) . . ?
C00C C008 H008 119.9 . . ?
C005 C009 H009 119.0 . . ?
N006 C009 C005 122.1(2) . . ?
N006 C009 H009 119.0 . . ?
C00G C00A P001 105.92(15) . . ?
C00G C00A C00H 109.2(2) . . ?
C00H C00A P001 108.33(16) . . ?
C00I C00A P001 113.87(15) . . ?
C00I C00A C00G 110.0(2) . . ?
C00I C00A C00H 109.4(2) . . ?
C007 C00B H00B 119.9 . . ?
C007 C00B C00E 120.1(2) . . ?
C00E C00B H00B 119.9 . . ?
C008 C00C H00C 120.0 . . ?
C00E C00C C008 120.0(2) . . ?
C00E C00C H00C 120.0 . . ?
N003 C00D H00D 118.9 . . ?
N003 C00D C00F 122.2(2) . . ?
C00F C00D H00D 118.9 . . ?
C00B C00E H00E 119.9 . . ?
C00C C00E C00B 120.2(2) . . ?
C00C C00E H00E 119.9 . . ?
N006 C00F C00D 122.8(2) . . ?
N006 C00F H00F 118.6 . . ?
C00D C00F H00F 118.6 . . ?
C00A C00G H00A 109.5 . . ?
C00A C00G H00G 109.5 . . ?
C00A C00G H00H 109.5 . . ?
H00A C00G H00G 109.5 . . ?
H00A C00G H00H 109.5 . . ?
H00G C00G H00H 109.5 . . ?
C00A C00H H00I 109.5 . . ?
C00A C00H H00J 109.5 . . ?
C00A C00H H00K 109.5 . . ?
H00I C00H H00J 109.5 . . ?
H00I C00H H00K 109.5 . . ?
H00J C00H H00K 109.5 . . ?
C00A C00I H00L 109.5 . . ?
C00A C00I H00M 109.5 . . ?
C00A C00I H00N 109.5 . . ?
H00L C00I H00M 109.5 . . ?
H00L C00I H00N 109.5 . . ?
H00M C00I H00N 109.5 . . ?

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
P001 C004 C007 C00B 179.29(18) . . . . ?
P001 C004 C008 C00C -179.21(17) . . . . ?
P001 C005 C009 N006 176.67(19) . . . . ?
O002 P001 C004 C007 -163.76(16) . . . . ?
O002 P001 C004 C008 15.33(18) . . . . ?
O002 P001 C005 N003 179.76(15) . . . . ?
O002 P001 C005 C009 0.67(19) . . . . ?
O002 P001 C00A C00G -50.5(2) . . . . ?
O002 P001 C00A C00H 66.5(2) . . . . ?
O002 P001 C00A C00I -171.47(19) . . . . ?
N003 C005 C009 N006 -2.4(3) . . . . ?
N003 C00D C00F N006 -2.3(4) . . . . ?
C004 P001 C005 N003 58.73(17) . . . . ?
C004 P001 C005 C009 -120.36(17) . . . . ?
C004 P001 C00A C00G 73.7(2) . . . . ?
C004 P001 C00A C00H -169.25(19) . . . . ?
C004 P001 C00A C00I -47.3(2) . . . . ?
C004 C007 C00B C00E 0.0(4) . . . . ?
C004 C008 C00C C00E -0.3(3) . . . . ?
C005 P001 C004 C007 -44.17(18) . . . . ?
C005 P001 C004 C008 134.92(16) . . . . ?
C005 P001 C00A C00G -171.38(19) . . . . ?
C005 P001 C00A C00H -54.3(2) . . . . ?
C005 P001 C00A C00I 67.7(2) . . . . ?
C005 N003 C00D C00F 0.7(3) . . . . ?
C007 C004 C008 C00C -0.1(3) . . . . ?
C007 C00B C00E C00C -0.4(4) . . . . ?
C008 C004 C007 C00B 0.2(3) . . . . ?
C008 C00C C00E C00B 0.5(4) . . . . ?
C009 N006 C00F C00D 1.4(4) . . . . ?
C00A P001 C004 C007 71.91(19) . . . . ?
C00A P001 C004 C008 -109.00(16) . . . . ?
C00A P001 C005 N003 -57.86(18) . . . . ?
C00A P001 C005 C009 123.05(17) . . . . ?
C00D N003 C005 P001 -177.52(16) . . . . ?
C00D N003 C005 C009 1.5(3) . . . . ?
C00F N006 C009 C005 0.8(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
