# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_jcm011
_database_code_depnum_ccdc_archive 'CCDC 2115990'
loop_
_audit_author_name
_audit_author_address
'Kristof Van Hecke'
;Ghent University
Belgium
;
_audit_update_record             
;
2021-10-15 deposited with the CCDC.	2021-11-22 downloaded from the CCDC.
;
_audit_creation_date             2019-07-30
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H18 N O4 P'
_chemical_formula_sum            'C12 H18 N O4 P'
_chemical_formula_weight         271.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H18 N O4 P'
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                   10.6343(2)
_cell_length_b                   6.96240(10)
_cell_length_c                   18.1231(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.140(2)
_cell_angle_gamma                90
_cell_volume                     1341.57(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8390
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      74.6390
_cell_measurement_theta_min      4.7550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.896
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.779
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 0 10 0.1180
-2 4 0 0.0748
2 -4 -1 0.0389
1 -4 -7 0.0411
-2 3 -8 0.0536
6 0 -5 0.0267
-6 1 5 0.0342
-5 -1 7 0.0380
3 -4 3 0.0682
2 3 -8 0.0545
-6 2 3 0.0405
-3 4 -4 0.0624

_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.062
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.5911 0.4451 9.8633 -0.8063 0.3834 0.4503
-2.2982 4.2594 0.4148 -0.4302 0.0120 -0.9026
2.2621 -4.2618 -0.7451 0.4559 -0.0126 0.8899
1.1632 -3.5568 -7.0134 0.8733 -0.0229 0.4867
-2.4266 2.6596 -8.4866 0.4057 -0.0093 -0.9140
6.1876 -0.1686 -5.4055 0.4221 0.8858 0.1932
-6.3051 0.5726 4.7688 -0.4110 -0.8622 -0.2960
-5.4375 -1.0243 6.9134 -0.4267 -0.8964 0.1204
3.4962 -3.6438 3.4928 0.0697 0.1434 0.9872
2.1808 3.1081 -7.7492 0.2994 0.6309 -0.7157
-6.2898 1.5360 2.9771 -0.3641 -0.7631 -0.5340
-2.8559 3.7550 -4.2895 -0.0199 -0.0388 -0.9991

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            24185
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.209
_diffrn_reflns_theta_min         4.780
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00  31.00   1.00    1.00    --  -41.68  57.00  90.00  101
  2  ω   -118.00  -9.00   1.00    1.00    --  -41.68 -77.00 -30.00  109
  3  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00-120.00  101
  4  ω     23.00  98.00   1.00    1.00    --   41.68-125.00 -60.00   75
  5  ω     17.00 116.00   1.00    1.00    --   41.68  38.00  30.00   99
  6  ω      1.00  83.00   1.00    1.00    --   41.68 -99.00-180.00   82
  7  ω     80.00 178.00   1.00   10.00    --  109.13  61.00 -30.00   98
  8  ω     33.00 142.00   1.00   10.00    --  109.13 -77.00   0.00  109
  9  ω     77.00 178.00   1.00   10.00    --  109.13  77.00 -90.00  101
 10  ω     80.00 178.00   1.00   10.00    --  109.13  61.00 -60.00   98
 11  ω     77.00 178.00   1.00   10.00    --  109.13  77.00 -60.00  101
 12  ω     94.00 178.00   1.00   10.00    --  109.13 125.00  90.00   84
 13  ω     83.00 178.00   1.00   10.00    --  109.13  45.00   0.00   95
 14  ω     83.00 178.00   1.00   10.00    --  109.13  45.00 150.00   95
 15  ω     33.00 137.00   1.00   10.00    --  109.13 -30.00 -30.00  104
 16  ω     83.00 178.00   1.00   10.00    --  109.13  45.00 -90.00   95
 17  ω     83.00 178.00   1.00   10.00    --  109.13  45.00 -30.00   95
 18  ω     80.00 178.00   1.00   10.00    --  109.13  61.00 -90.00   98
 19  ω     83.00 178.00   1.00   10.00    --  109.13  45.00  30.00   95
 20  ω     83.00 178.00   1.00   10.00    --  109.13  45.00 -60.00   95
 21  ω     81.00 178.00   1.00   10.00    --  109.13  30.00 -30.00   97
 22  ω     77.00 178.00   1.00   10.00    --  109.13  77.00 -30.00  101
 23  ω     80.00 178.00   1.00   10.00    --  109.13  61.00   0.00   98
 24  ω   -118.00  -9.00   1.00    1.00    --  -41.68 -77.00-180.00  109
 25  ω   -118.00  -9.00   1.00    1.00    --  -41.68 -77.00-120.00  109
 26  ω   -118.00  -9.00   1.00    1.00    --  -41.68 -77.00  90.00  109
 27  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00 120.00  101
 28  ω      9.00 118.00   1.00    1.00    --   41.68  77.00  90.00  109
 29  ω     14.00 115.00   1.00    1.00    --   41.68  57.00  60.00  101
 30  ω      1.00  83.00   1.00    1.00    --   41.68 -99.00 -30.00   82
 31  ω     36.00 117.00   1.00   10.00    --  109.13-125.00 -90.00   81
 32  ω     77.00 178.00   1.00   10.00    --  109.13  77.00  60.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0015632000
_diffrn_orient_matrix_UB_12      -0.0943542000
_diffrn_orient_matrix_UB_13      -0.0769248000
_diffrn_orient_matrix_UB_21      0.1336689000
_diffrn_orient_matrix_UB_22      0.0762271000
_diffrn_orient_matrix_UB_23      -0.0132304000
_diffrn_orient_matrix_UB_31      0.0556527000
_diffrn_orient_matrix_UB_32      -0.1851786000
_diffrn_orient_matrix_UB_33      0.0337496000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2369
_reflns_number_total             2755
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2755
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0386
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0638P)²+0.2734P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1095
_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, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(N1A) = Uanis(N1B)
Uanis(O4A) = Uanis(O4B)
3. Others
 Sof(O4B)=Sof(H4B)=Sof(N1B)=1-FVAR(1)
 Sof(O4A)=Sof(H4A)=Sof(N1A)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C9(H9A,H9B), C11(H11A,H11B)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8)
4.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C)
4.d Idealised tetrahedral OH refined as rotating group:
 O4A(H4A), O4B(H4B)
;
_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
P1 P 0.40337(4) 0.19639(6) 0.36338(2) 0.02800(14) Uani 1 1 d . . . . .
O1 O 0.43859(11) -0.00227(17) 0.38238(7) 0.0353(3) Uani 1 1 d . . . . .
O2 O 0.40288(11) 0.25017(18) 0.27957(6) 0.0327(3) Uani 1 1 d . . . . .
O3 O 0.26587(11) 0.25041(18) 0.38709(6) 0.0330(3) Uani 1 1 d . . . . .
C1 C 0.51377(16) 0.3643(2) 0.40378(8) 0.0300(3) Uani 1 1 d . . . . .
C2 C 0.63279(16) 0.2913(3) 0.44073(9) 0.0320(3) Uani 1 1 d . . . . .
H2A H 0.614339 0.171381 0.467794 0.038 Uiso 1 1 calc R . . . .
H2B H 0.663735 0.387555 0.476975 0.038 Uiso 1 1 calc R . . . .
C3 C 0.73443(15) 0.2526(3) 0.38474(8) 0.0304(3) Uani 1 1 d . . . . .
C4 C 0.76582(17) 0.0657(3) 0.36495(9) 0.0372(4) Uani 1 1 d . . . . .
H4 H 0.724055 -0.039647 0.387035 0.045 Uiso 1 1 calc R . . . .
C5 C 0.85812(18) 0.0321(4) 0.31296(10) 0.0458(5) Uani 1 1 d . . . . .
H5 H 0.879398 -0.095916 0.300030 0.055 Uiso 1 1 calc R . . . .
C6 C 0.91862(17) 0.1841(4) 0.28024(10) 0.0469(5) Uani 1 1 d . . . . .
H6 H 0.981836 0.160885 0.245020 0.056 Uiso 1 1 calc R . . . .
C7 C 0.88714(17) 0.3705(4) 0.29876(10) 0.0450(5) Uani 1 1 d . . . . .
H7 H 0.927950 0.475214 0.275665 0.054 Uiso 1 1 calc R . . . .
C8 C 0.79586(16) 0.4052(3) 0.35114(9) 0.0370(4) Uani 1 1 d . . . . .
H8 H 0.775347 0.533498 0.364043 0.044 Uiso 1 1 calc R . . . .
C9 C 0.32030(17) 0.1525(3) 0.22610(10) 0.0365(4) Uani 1 1 d . . . . .
H9A H 0.231075 0.176671 0.237640 0.044 Uiso 1 1 calc R . . . .
H9B H 0.335416 0.012270 0.227494 0.044 Uiso 1 1 calc R . . . .
C10 C 0.3497(2) 0.2313(3) 0.15116(10) 0.0442(4) Uani 1 1 d . . . . .
H10A H 0.292718 0.174128 0.114122 0.066 Uiso 1 1 calc GR . . . .
H10B H 0.436845 0.200168 0.139214 0.066 Uiso 1 1 calc GR . . . .
H10C H 0.338769 0.371101 0.151284 0.066 Uiso 1 1 calc GR . . . .
C11 C 0.22415(15) 0.1900(3) 0.45976(8) 0.0314(3) Uani 1 1 d . . . . .
H11A H 0.280667 0.243494 0.498656 0.038 Uiso 1 1 calc R . . . .
H11B H 0.226030 0.048156 0.463484 0.038 Uiso 1 1 calc R . . . .
C12 C 0.09272(18) 0.2619(3) 0.46972(11) 0.0460(5) Uani 1 1 d . . . . .
H12A H 0.037862 0.210605 0.430362 0.069 Uiso 1 1 calc GR . . . .
H12B H 0.092238 0.402591 0.467602 0.069 Uiso 1 1 calc GR . . . .
H12C H 0.062129 0.219678 0.517724 0.069 Uiso 1 1 calc GR . . . .
O4A O 0.55130(15) 0.6750(2) 0.41847(9) 0.0260(3) Uani 0.6707(19) 1 d . . P A 1
H4A H 0.520071 0.784748 0.412073 0.039 Uiso 0.6707(19) 1 calc GR . P A 1
N1A N 0.4686(2) 0.5367(3) 0.39045(11) 0.0241(4) Uani 0.6707(19) 1 d . . P A 1
O4B O 0.4161(3) 0.6227(5) 0.37715(18) 0.0260(3) Uani 0.3293(19) 1 d . . P A 2
H4B H 0.417920 0.743311 0.378407 0.039 Uiso 0.3293(19) 1 calc GR . P A 2
N1B N 0.5231(4) 0.5503(7) 0.4120(2) 0.0241(4) Uani 0.3293(19) 1 d . . P A 2


_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 O1 1.4720(12) . ?
P1 O2 1.5642(12) . ?
P1 O3 1.5777(11) . ?
P1 C1 1.8021(18) . ?
O2 C9 1.462(2) . ?
O3 C11 1.4600(18) . ?
C1 C2 1.508(2) . ?
C1 N1A 1.313(3) . ?
C1 N1B 1.307(5) . ?
C2 C3 1.521(2) . ?
C3 C4 1.392(3) . ?
C3 C8 1.394(2) . ?
C4 C5 1.394(3) . ?
C5 C6 1.379(3) . ?
C6 C7 1.383(3) . ?
C7 C8 1.392(3) . ?
C9 C10 1.503(2) . ?
C11 C12 1.499(2) . ?
O4A N1A 1.393(3) . ?
O4B N1B 1.385(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
O1 P1 O2 116.62(7) . . ?
O1 P1 O3 113.15(7) . . ?
O1 P1 C1 110.73(8) . . ?
O2 P1 O3 102.84(6) . . ?
O2 P1 C1 103.23(7) . . ?
O3 P1 C1 109.54(7) . . ?
C9 O2 P1 121.51(11) . . ?
C11 O3 P1 118.49(10) . . ?
C2 C1 P1 119.73(12) . . ?
N1A C1 P1 106.57(15) . . ?
N1A C1 C2 133.66(18) . . ?
N1B C1 P1 137.4(2) . . ?
N1B C1 C2 102.9(3) . . ?
C1 C2 C3 111.39(13) . . ?
C4 C3 C2 120.98(16) . . ?
C4 C3 C8 118.89(16) . . ?
C8 C3 C2 120.11(16) . . ?
C3 C4 C5 120.45(19) . . ?
C6 C5 C4 120.2(2) . . ?
C5 C6 C7 119.90(17) . . ?
C6 C7 C8 120.24(19) . . ?
C7 C8 C3 120.32(19) . . ?
O2 C9 C10 107.22(15) . . ?
O3 C11 C12 108.25(14) . . ?
C1 N1A O4A 109.79(19) . . ?
C1 N1B O4B 104.5(4) . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.861
_oxdiff_exptl_absorpt_empirical_full_min 0.528

####################################################################### 
# 
# 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_jcm015
_database_code_depnum_ccdc_archive 'CCDC 2115991'
loop_
_audit_author_name
_audit_author_address
'Kristof Van Hecke'
;Ghent University
Belgium
;
_audit_update_record             
;
2021-10-15 deposited with the CCDC.	2021-11-22 downloaded from the CCDC.
;
_audit_creation_date             2019-07-31
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H22 N O4 P'
_chemical_formula_sum            'C14 H22 N O4 P'
_chemical_formula_weight         299.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H22 N O4 P'
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/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                   17.0855(2)
_cell_length_b                   8.08470(10)
_cell_length_c                   11.59340(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.2960(10)
_cell_angle_gamma                90
_cell_volume                     1591.75(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12996
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      73.8210
_cell_measurement_theta_min      5.1880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.644
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.739
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -5 0 0.0805
1 5 0 0.0575
1 0 -8 0.1251
-1 0 8 0.1481
-11 0 -1 0.0344
11 0 1 0.0174

_exptl_crystal_size_max          0.281
_exptl_crystal_size_mid          0.138
_exptl_crystal_size_min          0.052
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.8089 -5.2345 0.0462 -0.6368 0.7449 -0.1988
0.8089 5.2345 -0.0462 0.6368 -0.7449 0.1988
1.0748 -0.1559 -7.5225 -0.1453 0.1685 0.9749
-1.0748 0.1559 7.5225 0.1453 -0.1685 -0.9749
-10.8983 -0.0890 -0.5600 -0.8220 -0.5658 0.0650
10.8983 0.0890 0.5600 0.8220 0.5658 -0.0650

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            28966
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.962
_diffrn_reflns_theta_min         2.602
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -14.00   1.00    2.00    --  -41.68 -57.00  90.00  101
  2  ω    -66.00  33.00   1.00    2.00    --  -41.68  38.00-120.00   99
  3  ω   -122.00  -1.00   1.00    2.00    --  -41.68 -19.00 -30.00  121
  4  ω    -66.00  33.00   1.00    2.00    --  -41.68  38.00 150.00   99
  5  ω     27.00  98.00   1.00    2.00    --   41.68-125.00-120.00   71
  6  ω     23.00 107.00   1.00   10.00    --  106.01 -94.00  90.00   84
  7  ω     33.00 112.00   1.00   10.00    --  106.01-125.00  60.00   79
  8  ω     97.00 178.00   1.00   10.00    --  106.01 125.00 -60.00   81
  9  ω     30.00 134.00   1.00   10.00    --  106.01 -30.00 -60.00  104
 10  ω     24.00 159.00   1.00   10.00    --  106.01 -15.00  90.00  135
 11  ω     34.00 120.00   1.00   10.00    --  106.01-135.00   3.00   86
 12  ω    103.00 178.00   1.00   10.00    --  106.01  77.00 120.00   75
 13  ω     33.00 112.00   1.00   10.00    --  106.01-125.00-180.00   79
 14  ω     33.00 132.00   1.00   10.00    --  106.01 -45.00-180.00   99
 15  ω     33.00 112.00   1.00   10.00    --  106.01-125.00 -90.00   79
 16  ω     80.00 178.00   1.00   10.00    --  106.01  45.00 -90.00   98
 17  ω    103.00 178.00   1.00   10.00    --  106.01  77.00-120.00   75
 18  ω   -115.00 -14.00   1.00    2.00    --  -41.68 -57.00   0.00  101
 19  ω   -115.00 -14.00   1.00    2.00    --  -41.68 -57.00 150.00  101
 20  ω   -116.00 -17.00   1.00    2.00    --  -41.68 -38.00-180.00   99
 21  ω    -87.00  -6.00   1.00    2.00    --  -41.68 125.00 -60.00   81
 22  ω   -115.00 -14.00   1.00    2.00    --  -41.68 -57.00 -60.00  101
 23  ω     77.00 178.00   1.00   10.00    --  106.01  61.00 -30.00  101
 24  ω     77.00 178.00   1.00   10.00    --  106.01  61.00   0.00  101
 25  ω     53.00 178.00   1.00   10.00    --  106.01  15.00-180.00  125
 26  ω     77.00 178.00   1.00   10.00    --  106.01  61.00 -60.00  101
 27  ω     77.00 178.00   1.00   10.00    --  106.01  61.00  90.00  101
 28  ω     77.00 178.00   1.00   10.00    --  106.01  61.00-150.00  101
 29  ω     77.00 178.00   1.00   10.00    --  106.01  61.00-180.00  101
 30  ω     77.00 178.00   1.00   10.00    --  106.01  61.00 150.00  101
 31  ω     78.00 178.00   1.00   10.00    --  106.01  30.00  60.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0731074000
_diffrn_orient_matrix_UB_12      0.1106064000
_diffrn_orient_matrix_UB_13      0.0274637000
_diffrn_orient_matrix_UB_21      0.0537444000
_diffrn_orient_matrix_UB_22      -0.1507184000
_diffrn_orient_matrix_UB_23      -0.0115909000
_diffrn_orient_matrix_UB_31      0.0004340000
_diffrn_orient_matrix_UB_32      0.0367639000
_diffrn_orient_matrix_UB_33      -0.1303037000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2895
_reflns_number_total             3197
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0339
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0497P)²+0.6287P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0923
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4A), C5(H5), C6(H6), C7(H7), C8(H8)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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
P1 P 0.32351(2) 0.47028(4) 0.47613(3) 0.02062(11) Uani 1 1 d . . . . .
O1 O 0.36906(6) 0.49191(12) 0.37609(8) 0.0253(2) Uani 1 1 d . . . . .
O2 O 0.23330(6) 0.50691(12) 0.45479(9) 0.0267(2) Uani 1 1 d . . . . .
O3 O 0.35238(5) 0.57959(12) 0.58351(8) 0.0235(2) Uani 1 1 d . . . . .
O4 O 0.33430(6) 0.05886(13) 0.65094(9) 0.0292(2) Uani 1 1 d . . . . .
H4 H 0.346346 0.043528 0.722342 0.044 Uiso 1 1 calc GR . . . .
N1 N 0.33975(6) 0.22644(15) 0.62607(10) 0.0249(2) Uani 1 1 d . . . . .
C1 C 0.32098(7) 0.25614(16) 0.51783(11) 0.0214(3) Uani 1 1 d . . . . .
C2 C 0.29552(8) 0.13166(16) 0.42376(12) 0.0237(3) Uani 1 1 d . . . . .
H2A H 0.313147 0.020001 0.450307 0.028 Uiso 1 1 calc R . . . .
H2B H 0.321211 0.158405 0.353567 0.028 Uiso 1 1 calc R . . . .
C3 C 0.20673(8) 0.13043(16) 0.39289(12) 0.0242(3) Uani 1 1 d . . . . .
C4 C 0.17455(9) 0.1274(2) 0.27770(14) 0.0344(3) Uani 1 1 d . . . . .
H4A H 0.208309 0.124700 0.217846 0.041 Uiso 1 1 calc R . . . .
C5 C 0.09338(10) 0.1282(2) 0.24905(16) 0.0447(4) Uani 1 1 d . . . . .
H5 H 0.072009 0.125126 0.169897 0.054 Uiso 1 1 calc R . . . .
C6 C 0.04377(9) 0.1336(2) 0.33518(17) 0.0433(4) Uani 1 1 d . . . . .
H6 H -0.011690 0.135258 0.315525 0.052 Uiso 1 1 calc R . . . .
C7 C 0.07522(9) 0.1365(2) 0.45033(16) 0.0381(4) Uani 1 1 d . . . . .
H7 H 0.041246 0.140152 0.509898 0.046 Uiso 1 1 calc R . . . .
C8 C 0.15622(9) 0.13398(18) 0.47911(13) 0.0297(3) Uani 1 1 d . . . . .
H8 H 0.177347 0.134718 0.558399 0.036 Uiso 1 1 calc R . . . .
C9 C 0.19888(9) 0.66437(18) 0.41109(14) 0.0328(3) Uani 1 1 d . . . . .
H9 H 0.231192 0.758391 0.446326 0.039 Uiso 1 1 calc R . . . .
C10 C 0.19662(12) 0.6707(3) 0.28193(17) 0.0554(5) Uani 1 1 d . . . . .
H10A H 0.250519 0.672283 0.260450 0.083 Uiso 1 1 calc GR . . . .
H10B H 0.168913 0.770961 0.252700 0.083 Uiso 1 1 calc GR . . . .
H10C H 0.168959 0.573133 0.247952 0.083 Uiso 1 1 calc GR . . . .
C11 C 0.11831(10) 0.6698(2) 0.45110(17) 0.0457(4) Uani 1 1 d . . . . .
H11A H 0.087418 0.575133 0.418871 0.069 Uiso 1 1 calc GR . . . .
H11B H 0.091930 0.772726 0.424514 0.069 Uiso 1 1 calc GR . . . .
H11C H 0.122966 0.665004 0.536041 0.069 Uiso 1 1 calc GR . . . .
C12 C 0.43725(7) 0.60563(16) 0.61928(11) 0.0218(3) Uani 1 1 d . . . . .
H12 H 0.467752 0.506775 0.597909 0.026 Uiso 1 1 calc R . . . .
C13 C 0.44512(9) 0.6248(2) 0.74929(12) 0.0302(3) Uani 1 1 d . . . . .
H13A H 0.413815 0.719755 0.769900 0.045 Uiso 1 1 calc GR . . . .
H13B H 0.500556 0.642846 0.778109 0.045 Uiso 1 1 calc GR . . . .
H13C H 0.426125 0.524332 0.784437 0.045 Uiso 1 1 calc GR . . . .
C14 C 0.46403(8) 0.75671(18) 0.55833(12) 0.0276(3) Uani 1 1 d . . . . .
H14A H 0.456074 0.739199 0.474215 0.041 Uiso 1 1 calc GR . . . .
H14B H 0.520023 0.776287 0.582585 0.041 Uiso 1 1 calc GR . . . .
H14C H 0.433398 0.852890 0.578557 0.041 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
P1 O1 1.4763(10) . ?
P1 O2 1.5622(10) . ?
P1 O3 1.5619(9) . ?
P1 C1 1.7993(14) . ?
O2 C9 1.4690(17) . ?
O3 C12 1.4789(14) . ?
O4 N1 1.3904(16) . ?
N1 C1 1.2834(18) . ?
C1 C2 1.5124(18) . ?
C2 C3 1.5200(18) . ?
C3 C4 1.388(2) . ?
C3 C8 1.391(2) . ?
C4 C5 1.390(2) . ?
C5 C6 1.380(3) . ?
C6 C7 1.384(3) . ?
C7 C8 1.388(2) . ?
C9 C10 1.494(3) . ?
C9 C11 1.501(2) . ?
C12 C13 1.5065(18) . ?
C12 C14 1.5071(19) . ?

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
O1 P1 O2 116.69(6) . . ?
O1 P1 O3 114.30(5) . . ?
O1 P1 C1 110.81(6) . . ?
O2 P1 C1 99.94(5) . . ?
O3 P1 O2 103.82(5) . . ?
O3 P1 C1 110.18(6) . . ?
C9 O2 P1 124.72(9) . . ?
C12 O3 P1 121.22(8) . . ?
C1 N1 O4 111.71(11) . . ?
N1 C1 P1 115.60(10) . . ?
N1 C1 C2 127.00(12) . . ?
C2 C1 P1 117.39(9) . . ?
C1 C2 C3 112.02(11) . . ?
C4 C3 C2 120.44(13) . . ?
C4 C3 C8 118.72(13) . . ?
C8 C3 C2 120.84(12) . . ?
C3 C4 C5 120.63(15) . . ?
C6 C5 C4 120.22(16) . . ?
C5 C6 C7 119.64(15) . . ?
C6 C7 C8 120.22(15) . . ?
C7 C8 C3 120.57(14) . . ?
O2 C9 C10 109.92(13) . . ?
O2 C9 C11 105.35(13) . . ?
C10 C9 C11 112.64(14) . . ?
O3 C12 C13 105.81(10) . . ?
O3 C12 C14 108.82(10) . . ?
C13 C12 C14 112.78(12) . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.456
_oxdiff_exptl_absorpt_empirical_full_min 0.774

