# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 2286021'
loop_
_audit_author_name
_audit_author_address
'Runbo Sun'
;Nanchang University
China
;
_audit_update_record             
;
2023-08-01 deposited with the CCDC.	2024-06-03 downloaded from the CCDC.
;
_audit_creation_date             2022-09-23
_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         '0.2(C16 H16 N O3 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 0.0033 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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   22.033(2)
_cell_length_b                   13.718(2)
_cell_length_c                   10.1323(12)
_cell_angle_alpha                90
_cell_angle_beta                 97.804(3)
_cell_angle_gamma                90
_cell_volume                     3034.0(7)
_cell_formula_units_Z            40
_cell_measurement_reflns_used    3029
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.35
_cell_measurement_theta_min      2.58
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.625
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6763
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0739 before and 0.0273 after correction.
The Ratio of minimum to maximum transmission is 0.9071.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             1480
_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  0.0255
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9104
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.779
_diffrn_reflns_theta_min         1.866
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2660
_reflns_number_total             3494
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.701
_refine_diff_density_min         -1.040
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         3494
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0881
_refine_ls_restrained_S_all      1.037
_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)+(0.1305P)²+13.1102P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2345
_refine_ls_wR_factor_ref         0.2628
_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:
 C00A(H00C), C00B(H00D), C00C(H00E), C00D(H00F), C00E(H00G), C00F(H00H),
 C00G(H00I), C00H(H00J), C00I(H00K), C00J(H00L), C00K(H00M)
2.b Idealised Me refined as rotating group:
 C00L(H00N,H00O,H00P)
;
_atom_sites_solution_hydrogens   mixed
_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 0.30586(4) 0.62787(7) 0.14662(9) 0.0337(3) Uiso 1 1 d . . . . .
O002 O 0.28078(13) 0.6431(2) 0.0051(3) 0.0444(7) Uiso 1 1 d . . . . .
O003 O 0.43144(15) 0.8827(2) 0.3365(3) 0.0549(8) Uiso 1 1 d . . . . .
O004 O 0.49278(14) 0.7653(2) 0.4331(3) 0.0560(8) Uiso 1 1 d . . . . .
N005 N 0.32708(18) 0.8180(3) 0.1757(4) 0.0470(8) Uiso 1 1 d . . . . .
C006 C 0.24787(17) 0.6176(3) 0.2543(4) 0.0367(8) Uiso 1 1 d . . . . .
C007 C 0.35265(16) 0.5205(3) 0.1700(4) 0.0360(8) Uiso 1 1 d . . . . .
C008 C 0.44266(18) 0.7967(3) 0.3540(4) 0.0416(8) Uiso 1 1 d . . . . .
C009 C 0.35237(16) 0.7317(3) 0.2129(4) 0.0364(8) Uiso 1 1 d . . . . .
C00A C 0.40567(18) 0.7175(3) 0.2950(4) 0.0416(8) Uiso 1 1 d . . . . .
H00C H 0.418827 0.653925 0.313808 0.050 Uiso 1 1 calc R . . . .
C00B C 0.18901(18) 0.5897(3) 0.1973(4) 0.0433(9) Uiso 1 1 d . . . . .
H00D H 0.180482 0.579664 0.105916 0.052 Uiso 1 1 calc R . . . .
C00C C 0.33695(19) 0.4424(3) 0.2452(4) 0.0455(9) Uiso 1 1 d . . . . .
H00E H 0.304377 0.448068 0.294221 0.055 Uiso 1 1 calc R . . . .
C00D C 0.1556(2) 0.5930(4) 0.4126(5) 0.0536(11) Uiso 1 1 d . . . . .
H00F H 0.124799 0.584547 0.466012 0.064 Uiso 1 1 calc R . . . .
C00E C 0.40225(19) 0.5113(3) 0.0990(4) 0.0470(9) Uiso 1 1 d . . . . .
H00G H 0.413193 0.563298 0.048197 0.056 Uiso 1 1 calc R . . . .
C00F C 0.2598(2) 0.6334(3) 0.3909(4) 0.0477(10) Uiso 1 1 d . . . . .
H00H H 0.298773 0.651686 0.429770 0.057 Uiso 1 1 calc R . . . .
C00G C 0.1433(2) 0.5770(3) 0.2779(5) 0.0524(10) Uiso 1 1 d . . . . .
H00I H 0.104325 0.557569 0.240409 0.063 Uiso 1 1 calc R . . . .
C00H C 0.4352(2) 0.4257(3) 0.1035(5) 0.0560(11) Uiso 1 1 d . . . . .
H00J H 0.468771 0.420590 0.057363 0.067 Uiso 1 1 calc R . . . .
C00I C 0.4183(2) 0.3474(4) 0.1764(5) 0.0585(12) Uiso 1 1 d . . . . .
H00K H 0.439909 0.289135 0.177313 0.070 Uiso 1 1 calc R . . . .
C00J C 0.3696(2) 0.3557(4) 0.2477(5) 0.0560(11) Uiso 1 1 d . . . . .
H00L H 0.358591 0.303216 0.297467 0.067 Uiso 1 1 calc R . . . .
C00K C 0.2133(2) 0.6217(3) 0.4690(5) 0.0556(11) Uiso 1 1 d . . . . .
H00M H 0.221058 0.633280 0.560207 0.067 Uiso 1 1 calc R . . . .
C00L C 0.5325(3) 0.8399(4) 0.4959(6) 0.0702(14) Uiso 1 1 d . . . . .
H00N H 0.541675 0.885873 0.429933 0.105 Uiso 1 1 calc GR . . . .
H00O H 0.569764 0.810815 0.537976 0.105 Uiso 1 1 calc GR . . . .
H00P H 0.512475 0.872898 0.561570 0.105 Uiso 1 1 calc GR . . . .
H00A H 0.297(3) 0.822(5) 0.115(7) 0.09(2) Uiso 1 1 d . . . . .
H00B H 0.351(2) 0.877(3) 0.220(5) 0.051(13) Uiso 1 1 d . . . . .

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P001 O002 1.480(3) . ?
P001 C006 1.795(4) . ?
P001 C007 1.795(4) . ?
P001 C009 1.828(4) . ?
O003 C008 1.212(5) . ?
O004 C008 1.344(5) . ?
O004 C00L 1.437(6) . ?
N005 C009 1.341(5) . ?
C006 C00B 1.399(5) . ?
C006 C00F 1.391(6) . ?
C007 C00C 1.385(5) . ?
C007 C00E 1.394(5) . ?
C008 C00A 1.440(6) . ?
C009 C00A 1.358(5) . ?
C00B C00G 1.391(6) . ?
C00C C00J 1.389(6) . ?
C00D C00G 1.372(6) . ?
C00D C00K 1.379(7) . ?
C00E C00H 1.378(6) . ?
C00F C00K 1.386(6) . ?
C00H C00I 1.383(7) . ?
C00I C00J 1.377(7) . ?

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 C006 113.40(17) . . ?
O002 P001 C007 112.08(17) . . ?
O002 P001 C009 111.30(16) . . ?
C006 P001 C007 107.37(17) . . ?
C006 P001 C009 104.33(17) . . ?
C007 P001 C009 107.90(17) . . ?
C008 O004 C00L 115.9(4) . . ?
C00B C006 P001 117.9(3) . . ?
C00F C006 P001 122.7(3) . . ?
C00F C006 C00B 119.5(4) . . ?
C00C C007 P001 121.7(3) . . ?
C00C C007 C00E 119.1(4) . . ?
C00E C007 P001 118.8(3) . . ?
O003 C008 O004 122.3(4) . . ?
O003 C008 C00A 125.5(4) . . ?
O004 C008 C00A 112.2(4) . . ?
N005 C009 P001 113.2(3) . . ?
N005 C009 C00A 126.2(4) . . ?
C00A C009 P001 120.5(3) . . ?
C009 C00A C008 122.7(4) . . ?
C00G C00B C006 119.8(4) . . ?
C007 C00C C00J 120.3(4) . . ?
C00G C00D C00K 120.2(4) . . ?
C00H C00E C007 120.4(4) . . ?
C00K C00F C006 119.8(4) . . ?
C00D C00G C00B 120.2(4) . . ?
C00E C00H C00I 120.1(5) . . ?
C00J C00I C00H 120.1(5) . . ?
C00I C00J C00C 120.0(5) . . ?
C00D C00K C00F 120.5(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
