# Supplementary Information (SI) for Green 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_rm2382
_database_code_depnum_ccdc_archive 'CCDC 2367667'
loop_
_audit_author_name
_audit_author_address
'B. Kariuki'
;Cardiff university
United Kingdom
;
_audit_update_record             
;
2024-07-03 deposited with the CCDC.	2024-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 N O3 P'
_chemical_formula_weight         365.35

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.5388(6)
_cell_length_b                   19.0742(9)
_cell_length_c                   9.8492(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.023(5)
_cell_angle_gamma                90
_cell_volume                     1893.13(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4034
_cell_measurement_theta_min      3.9760
_cell_measurement_theta_max      29.3370

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.165
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_T_min  0.623
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10099
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.531
_diffrn_reflns_theta_max         29.811
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.839
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4550
_reflns_number_gt                3577
_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.
 
 _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 1.171.42.90a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0430P)²+0.9622P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4550
_refine_ls_number_parameters     240
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1206
_refine_ls_wR_factor_gt          0.1085
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_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 0.59290(18) 0.18337(9) 0.28979(18) 0.0282(4) Uani 1 1 d . . . . .
C2 C 0.4659(2) 0.15744(11) 0.2731(2) 0.0394(5) Uani 1 1 d . . . . .
H2 H 0.398111 0.187931 0.283658 0.047 Uiso 1 1 calc R U . . .
C3 C 0.4377(2) 0.08739(12) 0.2411(3) 0.0527(6) Uani 1 1 d . . . . .
H3 H 0.351117 0.069828 0.231451 0.063 Uiso 1 1 calc R U . . .
C4 C 0.5348(3) 0.04314(12) 0.2233(3) 0.0527(6) Uani 1 1 d . . . . .
H4 H 0.514473 -0.004658 0.199616 0.063 Uiso 1 1 calc R U . . .
C5 C 0.6617(2) 0.06787(11) 0.2398(2) 0.0453(5) Uani 1 1 d . . . . .
H5 H 0.728573 0.037140 0.227877 0.054 Uiso 1 1 calc R U . . .
C6 C 0.6910(2) 0.13777(10) 0.2738(2) 0.0334(4) Uani 1 1 d . . . . .
H6 H 0.778411 0.154689 0.286277 0.040 Uiso 1 1 calc R U . . .
C7 C 0.48367(19) 0.32174(9) 0.2869(2) 0.0328(4) Uani 1 1 d . . . . .
C8 C 0.4350(2) 0.34063(12) 0.1445(2) 0.0462(5) Uani 1 1 d . . . . .
H8 H 0.484771 0.329990 0.080829 0.055 Uiso 1 1 calc R U . . .
C9 C 0.3147(3) 0.37473(14) 0.0955(3) 0.0617(7) Uani 1 1 d . . . . .
H9 H 0.281975 0.387462 -0.001748 0.074 Uiso 1 1 calc R U . . .
C10 C 0.2426(2) 0.39024(13) 0.1866(3) 0.0636(8) Uani 1 1 d . . . . .
H10 H 0.159027 0.412894 0.152005 0.076 Uiso 1 1 calc R U . . .
C11 C 0.2907(3) 0.37309(13) 0.3287(4) 0.0648(8) Uani 1 1 d . . . . .
H11 H 0.240584 0.384543 0.391572 0.078 Uiso 1 1 calc R U . . .
C12 C 0.4122(2) 0.33915(12) 0.3802(3) 0.0486(6) Uani 1 1 d . . . . .
H12 H 0.445871 0.328006 0.478235 0.058 Uiso 1 1 calc R U . . .
C13 C 0.78642(17) 0.36448(9) 0.25743(17) 0.0259(4) Uani 1 1 d . . . . .
C14 C 0.79305(19) 0.41129(9) 0.36897(18) 0.0298(4) Uani 1 1 d . . . . .
H14 H 0.761561 0.397521 0.446021 0.036 Uiso 1 1 calc R U . . .
C15 C 0.84540(18) 0.47740(9) 0.36660(18) 0.0294(4) Uani 1 1 d . . . . .
H15 H 0.849442 0.508842 0.442564 0.035 Uiso 1 1 calc R U . . .
C16 C 0.89257(17) 0.49907(9) 0.25481(18) 0.0289(4) Uani 1 1 d . . . . .
C17 C 0.88756(18) 0.45175(10) 0.14570(19) 0.0326(4) Uani 1 1 d . . . . .
H17 H 0.919986 0.465396 0.069230 0.039 Uiso 1 1 calc R U . . .
C18 C 0.83617(18) 0.38536(10) 0.14709(19) 0.0312(4) Uani 1 1 d . . . . .
H18 H 0.834621 0.353573 0.072361 0.037 Uiso 1 1 calc R U . . .
C19 C 0.94314(18) 0.57072(10) 0.2461(2) 0.0324(4) Uani 1 1 d . . . . .
C20 C 0.9654(2) 0.68590(11) 0.3434(3) 0.0460(5) Uani 1 1 d . . . . .
H20A H 0.921970 0.709069 0.251631 0.055 Uiso 1 1 calc R U . . .
H20B H 1.062555 0.686598 0.359358 0.055 Uiso 1 1 calc R U . . .
C21 C 0.9307(2) 0.72298(12) 0.4617(3) 0.0518(6) Uani 1 1 d . . . . .
H21A H 0.834183 0.723079 0.443216 0.078 Uiso 1 1 calc R U . . .
H21B H 0.963100 0.771385 0.467735 0.078 Uiso 1 1 calc R U . . .
H21C H 0.972277 0.698767 0.551447 0.078 Uiso 1 1 calc R U . . .
N1 N 0.73335(15) 0.29709(8) 0.25405(15) 0.0276(3) Uani 1 1 d D . . . .
O1 O 0.69447(14) 0.27802(7) 0.50337(12) 0.0337(3) Uani 1 1 d . . . . .
O2 O 0.99838(16) 0.58919(8) 0.16046(16) 0.0488(4) Uani 1 1 d . . . . .
O3 O 0.91838(14) 0.61400(7) 0.34213(15) 0.0384(3) Uani 1 1 d . . . . .
P1 P 0.63417(5) 0.27171(2) 0.34747(4) 0.02569(13) Uani 1 1 d . . . . .
H1 H 0.726(2) 0.2742(9) 0.1797(14) 0.033(6) Uiso 1 1 d 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
C1 C2 1.391(3) . ?
C1 C6 1.394(3) . ?
C1 P1 1.7907(18) . ?
C2 C3 1.385(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.377(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.388(3) . ?
C7 C8 1.393(3) . ?
C7 P1 1.7967(19) . ?
C8 C9 1.380(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.367(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.396(2) . ?
C13 N1 1.398(2) . ?
C13 C14 1.401(2) . ?
C14 C15 1.379(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.397(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.393(3) . ?
C16 C19 1.479(3) . ?
C17 C18 1.379(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 O2 1.209(2) . ?
C19 O3 1.337(2) . ?
C20 O3 1.457(2) . ?
C20 C21 1.496(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
N1 P1 1.6543(15) . ?
N1 H1 0.836(9) . ?
O1 P1 1.4849(12) . ?

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 C1 C6 118.96(17) . . ?
C2 C1 P1 120.53(15) . . ?
C6 C1 P1 120.24(14) . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 119.7(2) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 120.47(19) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C12 C7 C8 119.6(2) . . ?
C12 C7 P1 120.32(16) . . ?
C8 C7 P1 120.05(16) . . ?
C9 C8 C7 120.3(2) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.2(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C7 C12 C11 119.3(2) . . ?
C7 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C18 C13 N1 118.85(15) . . ?
C18 C13 C14 119.00(16) . . ?
N1 C13 C14 122.15(15) . . ?
C15 C14 C13 119.84(16) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 121.35(16) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C17 C16 C15 118.34(17) . . ?
C17 C16 C19 119.16(16) . . ?
C15 C16 C19 122.46(17) . . ?
C18 C17 C16 120.92(17) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C13 120.52(17) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
O2 C19 O3 123.16(18) . . ?
O2 C19 C16 124.41(18) . . ?
O3 C19 C16 112.41(16) . . ?
O3 C20 C21 107.00(18) . . ?
O3 C20 H20A 110.3 . . ?
C21 C20 H20A 110.3 . . ?
O3 C20 H20B 110.3 . . ?
C21 C20 H20B 110.3 . . ?
H20A C20 H20B 108.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C13 N1 P1 124.70(12) . . ?
C13 N1 H1 115.9(14) . . ?
P1 N1 H1 114.8(14) . . ?
C19 O3 C20 116.83(16) . . ?
O1 P1 N1 113.74(8) . . ?
O1 P1 C1 113.27(8) . . ?
N1 P1 C1 103.49(8) . . ?
O1 P1 C7 111.66(8) . . ?
N1 P1 C7 107.46(8) . . ?
C1 P1 C7 106.60(9) . . ?

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.049



####################################################################### 
# 
# 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_rm2343
_database_code_depnum_ccdc_archive 'CCDC 2367670'
loop_
_audit_author_name
_audit_author_address
'B. Kariuki'
;Cardiff university
United Kingdom
;
_audit_update_record             
;
2024-07-03 deposited with the CCDC.	2024-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 N O P'
_chemical_formula_weight         293.29

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

_cell_length_a                   16.9837(12)
_cell_length_b                   9.6048(6)
_cell_length_c                   9.6892(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1580.55(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2852
_cell_measurement_theta_min      4.1500
_cell_measurement_theta_max      25.4880

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.290
_exptl_absorpt_coefficient_mu    0.172
_shelx_estimated_absorpt_T_min   0.919
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_T_min  0.525
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7472
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.832
_diffrn_reflns_theta_max         29.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.724
_diffrn_reflns_point_group_measured_fraction_full 0.847
_reflns_number_total             3179
_reflns_number_gt                2320
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.554
_reflns_Friedel_fraction_max     0.548
_reflns_Friedel_fraction_full    0.677

_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 1.171.42.90a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0371P)²+0.2447P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 674 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(6)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3179
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1071
_refine_ls_wR_factor_gt          0.0927
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.085
_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 0.32681(19) 0.2510(3) 0.4319(4) 0.0569(8) Uani 1 1 d . . . . .
C2 C 0.3732(2) 0.1956(4) 0.5359(6) 0.0806(13) Uani 1 1 d . . . . .
H2 H 0.379994 0.243946 0.618175 0.097 Uiso 1 1 calc R U . . .
C3 C 0.4095(2) 0.0674(5) 0.5168(7) 0.0970(18) Uani 1 1 d . . . . .
H3 H 0.440289 0.030183 0.587039 0.116 Uiso 1 1 calc R U . . .
C4 C 0.4007(3) -0.0045(4) 0.3968(8) 0.101(2) Uani 1 1 d . . . . .
H4 H 0.426284 -0.089117 0.384190 0.122 Uiso 1 1 calc R U . . .
C5 C 0.3536(3) 0.0492(4) 0.2945(6) 0.0882(14) Uani 1 1 d . . . . .
H5 H 0.346734 -0.000406 0.212915 0.106 Uiso 1 1 calc R U . . .
C6 C 0.3159(2) 0.1771(3) 0.3115(4) 0.0671(11) Uani 1 1 d . . . . .
H6 H 0.283612 0.212143 0.242171 0.081 Uiso 1 1 calc R U . . .
C7 C 0.23381(19) 0.6314(3) 0.5233(4) 0.0569(9) Uani 1 1 d . . . . .
C8 C 0.1593(2) 0.6191(5) 0.5790(6) 0.0848(12) Uani 1 1 d . . . . .
H8 H 0.147425 0.544570 0.636599 0.102 Uiso 1 1 calc R U . . .
C9 C 0.1025(2) 0.7173(6) 0.5492(6) 0.0989(15) Uani 1 1 d . . . . .
H9 H 0.052081 0.706893 0.585227 0.119 Uiso 1 1 calc R U . . .
C10 C 0.1191(3) 0.8290(5) 0.4681(6) 0.0945(17) Uani 1 1 d . . . . .
H10 H 0.080849 0.896126 0.450988 0.113 Uiso 1 1 calc R U . . .
C11 C 0.1921(3) 0.8416(4) 0.4124(8) 0.114(2) Uani 1 1 d . . . . .
H11 H 0.203605 0.916745 0.355337 0.137 Uiso 1 1 calc R U . . .
C12 C 0.2495(2) 0.7432(4) 0.4399(6) 0.0902(14) Uani 1 1 d . . . . .
H12 H 0.299371 0.753091 0.401399 0.108 Uiso 1 1 calc R U . . .
C13 C 0.40152(18) 0.5726(3) 0.5389(3) 0.0534(8) Uani 1 1 d . . . . .
C14 C 0.4332(2) 0.6531(4) 0.6436(5) 0.0713(10) Uani 1 1 d . . . . .
H14 H 0.405071 0.665741 0.724909 0.086 Uiso 1 1 calc R U . . .
C15 C 0.5059(3) 0.7145(5) 0.6288(6) 0.0910(15) Uani 1 1 d . . . . .
H15 H 0.526360 0.768796 0.699739 0.109 Uiso 1 1 calc R U . . .
C16 C 0.5482(3) 0.6960(5) 0.5098(7) 0.0918(16) Uani 1 1 d . . . . .
H16 H 0.597228 0.737838 0.499588 0.110 Uiso 1 1 calc R U . . .
C17 C 0.5182(2) 0.6162(4) 0.4071(6) 0.0845(13) Uani 1 1 d . . . . .
H17 H 0.547452 0.602601 0.327154 0.101 Uiso 1 1 calc R U . . .
C18 C 0.4444(2) 0.5544(4) 0.4189(4) 0.0663(9) Uani 1 1 d . . . . .
H18 H 0.424119 0.501299 0.346900 0.080 Uiso 1 1 calc R U . . .
N1 N 0.28857(16) 0.3818(3) 0.4447(3) 0.0580(7) Uani 1 1 d . . . . .
H1 H 0.253507 0.401649 0.383791 0.070 Uiso 1 1 calc R U . . .
O1 O 0.29805(17) 0.4468(3) 0.7093(3) 0.0791(8) Uani 1 1 d . . . . .
P1 P 0.30499(5) 0.49923(9) 0.56530(13) 0.0534(2) Uani 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
C1 C6 1.378(5) . ?
C1 C2 1.385(6) . ?
C1 N1 1.420(4) . ?
C2 C3 1.389(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.360(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.371(5) . ?
C7 C8 1.380(5) . ?
C7 P1 1.799(3) . ?
C8 C9 1.380(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.360(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.358(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.384(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.382(5) . ?
C13 C14 1.384(5) . ?
C13 P1 1.803(3) . ?
C14 C15 1.375(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.370(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.355(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.392(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
N1 P1 1.647(3) . ?
N1 H1 0.8600 . ?
O1 P1 1.488(3) . ?

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
C6 C1 C2 119.6(3) . . ?
C6 C1 N1 117.9(3) . . ?
C2 C1 N1 122.4(4) . . ?
C1 C2 C3 119.7(5) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 121.0(5) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 119.4(4) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 120.8(5) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 119.5(4) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C12 C7 C8 118.4(4) . . ?
C12 C7 P1 123.7(3) . . ?
C8 C7 P1 117.9(3) . . ?
C9 C8 C7 120.1(5) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 121.0(4) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C11 C10 C9 119.3(4) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 120.4(5) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C7 C12 C11 120.8(4) . . ?
C7 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C18 C13 C14 118.8(3) . . ?
C18 C13 P1 123.3(3) . . ?
C14 C13 P1 117.9(3) . . ?
C15 C14 C13 120.8(4) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16 C15 C14 120.1(4) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 119.6(4) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 121.3(5) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C13 C18 C17 119.3(4) . . ?
C13 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C1 N1 P1 126.2(3) . . ?
C1 N1 H1 116.9 . . ?
P1 N1 H1 116.9 . . ?
O1 P1 N1 114.82(17) . . ?
O1 P1 C7 113.41(18) . . ?
N1 P1 C7 102.05(14) . . ?
O1 P1 C13 109.73(16) . . ?
N1 P1 C13 108.72(15) . . ?
C7 P1 C13 107.64(15) . . ?

_refine_diff_density_max         0.190
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.036



####################################################################### 
# 
# 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_rm2365
_database_code_depnum_ccdc_archive 'CCDC 2367668'
loop_
_audit_author_name
_audit_author_address
'B. Kariuki'
;Cardiff university
United Kingdom
;
_audit_update_record             
;
2024-07-03 deposited with the CCDC.	2024-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H11 O2 P'
_chemical_formula_weight         218.18

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'
P P 0.1023 0.0942 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   11.4422(6)
_cell_length_b                   6.0033(3)
_cell_length_c                   15.6542(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.064(5)
_cell_angle_gamma                90
_cell_volume                     1058.76(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3827
_cell_measurement_theta_min      3.5960
_cell_measurement_theta_max      29.4940

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.234
_shelx_estimated_absorpt_T_min   0.894
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_T_min  0.523
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8963
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.454
_diffrn_reflns_theta_max         29.539
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.864
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.864
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2558
_reflns_number_gt                2041
_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.
 
 _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 1.171.42.90a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0325P)²+0.6700P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2558
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1036
_refine_ls_wR_factor_gt          0.0914
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.001
_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 0.16256(15) 0.5334(3) 0.63890(12) 0.0223(4) Uani 1 1 d . . . . .
C2 C 0.12150(17) 0.3279(3) 0.60537(13) 0.0294(4) Uani 1 1 d . . . . .
H2 H 0.094075 0.220776 0.641927 0.035 Uiso 1 1 calc R U . . .
C3 C 0.12047(18) 0.2788(4) 0.51842(14) 0.0347(5) Uani 1 1 d . . . . .
H3 H 0.091849 0.138520 0.495636 0.042 Uiso 1 1 calc R U . . .
C4 C 0.16094(18) 0.4333(4) 0.46517(14) 0.0366(5) Uani 1 1 d . . . . .
H4 H 0.159268 0.399991 0.405639 0.044 Uiso 1 1 calc R U . . .
C5 C 0.2037(2) 0.6355(4) 0.49829(14) 0.0413(5) Uani 1 1 d . . . . .
H5 H 0.233227 0.740231 0.461822 0.050 Uiso 1 1 calc R U . . .
C6 C 0.20393(18) 0.6871(4) 0.58445(13) 0.0331(5) Uani 1 1 d . . . . .
H6 H 0.232424 0.827959 0.606619 0.040 Uiso 1 1 calc R U . . .
C7 C 0.31284(15) 0.6332(3) 0.80350(12) 0.0219(4) Uani 1 1 d . . . . .
C8 C 0.37500(18) 0.8314(3) 0.79757(13) 0.0306(4) Uani 1 1 d . . . . .
H8 H 0.336843 0.953174 0.765372 0.037 Uiso 1 1 calc R U . . .
C9 C 0.49179(19) 0.8507(4) 0.83839(15) 0.0415(6) Uani 1 1 d . . . . .
H9 H 0.534071 0.985142 0.833925 0.050 Uiso 1 1 calc R U . . .
C10 C 0.54681(19) 0.6744(4) 0.88560(16) 0.0453(6) Uani 1 1 d . . . . .
H10 H 0.626907 0.688670 0.914008 0.054 Uiso 1 1 calc R U . . .
C11 C 0.48691(19) 0.4778(4) 0.89203(15) 0.0406(5) Uani 1 1 d . . . . .
H11 H 0.525730 0.357149 0.924571 0.049 Uiso 1 1 calc R U . . .
C12 C 0.36949(17) 0.4561(3) 0.85081(13) 0.0291(4) Uani 1 1 d . . . . .
H12 H 0.328098 0.320498 0.855002 0.035 Uiso 1 1 calc R U . . .
P1 P 0.16210(4) 0.60614(7) 0.74992(3) 0.02062(14) Uani 1 1 d . . . . .
O1 O 0.11432(12) 0.8470(2) 0.75079(9) 0.0296(3) Uani 1 1 d . . . . .
H1 H 0.040524 0.846788 0.733694 0.044 Uiso 1 1 calc R U . . .
O2 O 0.09950(11) 0.4321(2) 0.79377(9) 0.0287(3) Uani 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
C1 C2 1.390(3) . ?
C1 C6 1.394(3) . ?
C1 P1 1.7927(19) . ?
C2 C3 1.391(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.389(3) . ?
C7 C8 1.398(3) . ?
C7 P1 1.7887(18) . ?
C8 C9 1.382(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.378(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.377(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
P1 O2 1.4995(13) . ?
P1 O1 1.5465(13) . ?
O1 H1 0.8400 . ?

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 C1 C6 119.01(18) . . ?
C2 C1 P1 121.61(15) . . ?
C6 C1 P1 119.38(14) . . ?
C1 C2 C3 120.16(19) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 120.15(19) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 120.4(2) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C12 C7 C8 119.42(18) . . ?
C12 C7 P1 120.15(14) . . ?
C8 C7 P1 120.42(15) . . ?
C9 C8 C7 120.2(2) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 119.9(2) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 119.9(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C7 C12 C11 119.89(19) . . ?
C7 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
O2 P1 O1 116.72(8) . . ?
O2 P1 C7 110.32(8) . . ?
O1 P1 C7 102.97(8) . . ?
O2 P1 C1 110.90(8) . . ?
O1 P1 C1 107.28(8) . . ?
C7 P1 C1 108.10(8) . . ?
P1 O1 H1 109.5 . . ?

_refine_diff_density_max         0.279
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.061



####################################################################### 
# 
# 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_rm2383
_database_code_depnum_ccdc_archive 'CCDC 2367671'
loop_
_audit_author_name
_audit_author_address
'B. Kariuki'
;Cardiff university
United Kingdom
;
_audit_update_record             
;
2024-07-03 deposited with the CCDC.	2024-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H15 O2 P'
_chemical_formula_weight         294.27

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'
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'

_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                   9.2605(4)
_cell_length_b                   11.3986(5)
_cell_length_c                   14.1564(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.665(3)
_cell_angle_gamma                90
_cell_volume                     1491.25(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5606
_cell_measurement_theta_min      3.5530
_cell_measurement_theta_max      28.7700

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.185
_shelx_estimated_absorpt_T_min   0.881
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_T_min  0.346
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13775
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.393
_diffrn_reflns_theta_max         29.780
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3683
_reflns_number_gt                2819
_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.
 
 _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 1.171.42.90a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0558P)²+1.8766P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3683
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0570
_refine_ls_wR_factor_ref         0.1550
_refine_ls_wR_factor_gt          0.1411
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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 0.8657(2) 0.31837(19) 0.36765(15) 0.0238(4) Uani 1 1 d . . . . .
C2 C 0.8893(2) 0.2043(2) 0.33675(16) 0.0274(5) Uani 1 1 d . . . . .
H2 H 0.844399 0.178060 0.278323 0.033 Uiso 1 1 calc R U . . .
C3 C 0.9780(3) 0.1292(2) 0.39106(18) 0.0340(5) Uani 1 1 d . . . . .
H3 H 0.994003 0.051495 0.369853 0.041 Uiso 1 1 calc R U . . .
C4 C 1.0434(3) 0.1675(2) 0.47652(19) 0.0381(6) Uani 1 1 d . . . . .
H4 H 1.105178 0.116082 0.513195 0.046 Uiso 1 1 calc R U . . .
C5 C 1.0194(3) 0.2798(3) 0.50860(18) 0.0386(6) Uani 1 1 d . . . . .
H5 H 1.063624 0.305281 0.567443 0.046 Uiso 1 1 calc R U . . .
C6 C 0.9303(3) 0.3552(2) 0.45442(16) 0.0308(5) Uani 1 1 d . . . . .
H6 H 0.913145 0.432298 0.476529 0.037 Uiso 1 1 calc R U . . .
C7 C 0.5663(2) 0.3900(2) 0.30891(17) 0.0298(5) Uani 1 1 d . . . . .
C8 C 0.4844(3) 0.4670(3) 0.3593(2) 0.0486(7) Uani 1 1 d . . . . .
H8 H 0.527674 0.534797 0.388081 0.058 Uiso 1 1 calc R U . . .
C9 C 0.3384(4) 0.4440(3) 0.3673(3) 0.0607(9) Uani 1 1 d . . . . .
H9 H 0.281984 0.496384 0.401822 0.073 Uiso 1 1 calc R U . . .
C10 C 0.2750(3) 0.3469(3) 0.3260(2) 0.0555(9) Uani 1 1 d . . . . .
H10 H 0.175075 0.332223 0.332285 0.067 Uiso 1 1 calc R U . . .
C11 C 0.3552(3) 0.2705(3) 0.2754(2) 0.0491(7) Uani 1 1 d . . . . .
H11 H 0.310604 0.203571 0.246118 0.059 Uiso 1 1 calc R U . . .
C12 C 0.5022(3) 0.2914(3) 0.26736(18) 0.0374(6) Uani 1 1 d . . . . .
H12 H 0.558278 0.238082 0.233394 0.045 Uiso 1 1 calc R U . . .
C13 C 0.9019(2) 0.3855(2) 0.14852(16) 0.0285(5) Uani 1 1 d . . . . .
C14 C 0.9229(3) 0.2905(3) 0.09161(19) 0.0396(6) Uani 1 1 d . . . . .
H14 H 0.853627 0.229015 0.086221 0.047 Uiso 1 1 calc R U . . .
C15 C 1.0473(4) 0.2859(3) 0.0420(2) 0.0512(8) Uani 1 1 d . . . . .
H15 H 1.062865 0.221053 0.001810 0.061 Uiso 1 1 calc R U . . .
C16 C 1.1480(3) 0.3744(3) 0.0505(2) 0.0506(8) Uani 1 1 d . . . . .
H16 H 1.233767 0.370039 0.017268 0.061 Uiso 1 1 calc R U . . .
C17 C 1.1243(3) 0.4685(3) 0.1071(2) 0.0519(8) Uani 1 1 d . . . . .
H17 H 1.193657 0.529936 0.112568 0.062 Uiso 1 1 calc R U . . .
C18 C 0.9998(3) 0.4756(3) 0.1567(2) 0.0433(7) Uani 1 1 d . . . . .
H18 H 0.982922 0.541615 0.195406 0.052 Uiso 1 1 calc R U . . .
O1 O 0.79344(19) 0.54425(15) 0.32824(13) 0.0357(4) Uani 1 1 d . . . . .
O2 O 0.76898(17) 0.38831(15) 0.19234(11) 0.0297(4) Uani 1 1 d . . . . .
P1 P 0.75509(6) 0.42267(5) 0.30090(4) 0.02658(17) Uani 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
C1 C2 1.393(3) . ?
C1 C6 1.396(3) . ?
C1 P1 1.798(2) . ?
C2 C3 1.385(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.384(4) . ?
C7 C8 1.387(4) . ?
C7 P1 1.798(2) . ?
C8 C9 1.388(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.366(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.376(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.393(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.370(4) . ?
C13 C14 1.370(4) . ?
C13 O2 1.414(3) . ?
C14 C15 1.388(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.374(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.365(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
O1 P1 1.4762(18) . ?
O2 P1 1.5991(17) . ?

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 C1 C6 119.3(2) . . ?
C2 C1 P1 123.19(17) . . ?
C6 C1 P1 117.49(18) . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.0(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.6(2) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C1 120.4(2) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C12 C7 C8 119.9(2) . . ?
C12 C7 P1 122.25(19) . . ?
C8 C7 P1 117.8(2) . . ?
C7 C8 C9 119.3(3) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 120.2(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 119.8(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C7 C12 C11 119.9(3) . . ?
C7 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C18 C13 C14 121.6(2) . . ?
C18 C13 O2 122.4(2) . . ?
C14 C13 O2 115.9(2) . . ?
C13 C14 C15 118.7(3) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 119.6(3) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 120.8(3) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C13 C18 C17 118.7(3) . . ?
C13 C18 H18 120.7 . . ?
C17 C18 H18 120.7 . . ?
C13 O2 P1 123.58(15) . . ?
O1 P1 O2 116.69(10) . . ?
O1 P1 C1 111.32(10) . . ?
O2 P1 C1 105.37(10) . . ?
O1 P1 C7 113.36(11) . . ?
O2 P1 C7 98.52(10) . . ?
C1 P1 C7 110.70(10) . . ?

_refine_diff_density_max         1.392
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.065



####################################################################### 
# 
# 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_rm2385
_database_code_depnum_ccdc_archive 'CCDC 2367669'
loop_
_audit_author_name
_audit_author_address
'B. Kariuki'
;Cardiff university
United Kingdom
;
_audit_update_record             
;
2024-07-03 deposited with the CCDC.	2024-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 N O2 P'
_chemical_formula_weight         309.29

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   15.6012(12)
_cell_length_b                   9.0207(5)
_cell_length_c                   11.7490(9)
_cell_angle_alpha                90
_cell_angle_beta                 107.452(8)
_cell_angle_gamma                90
_cell_volume                     1577.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2983
_cell_measurement_theta_min      3.8170
_cell_measurement_theta_max      26.5240

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.180
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_T_min  0.26609
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14047
_diffrn_reflns_av_unetI/netI     0.0894
_diffrn_reflns_av_R_equivalents  0.0729
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.431
_diffrn_reflns_theta_max         29.796
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.864
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.864
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.864
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3903
_reflns_number_gt                2361
_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.
 
 _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 1.171.42.90a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_structure_solution    SHELXT
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0568P)²+0.5942P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3903
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1203
_refine_ls_R_factor_gt           0.0620
_refine_ls_wR_factor_ref         0.1578
_refine_ls_wR_factor_gt          0.1278
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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 0.58610(18) 0.5860(3) 0.2914(2) 0.0307(6) Uani 1 1 d . . . . .
C2 C 0.5312(2) 0.5820(4) 0.3639(3) 0.0502(8) Uani 1 1 d . . . . .
H2 H 0.556687 0.565855 0.447168 0.060 Uiso 1 1 calc R U . . .
C3 C 0.4390(2) 0.6012(5) 0.3166(4) 0.0665(11) Uani 1 1 d . . . . .
H3 H 0.401814 0.597753 0.367463 0.080 Uiso 1 1 calc R U . . .
C4 C 0.4016(2) 0.6252(4) 0.1964(3) 0.0553(9) Uani 1 1 d . . . . .
H4 H 0.338398 0.636850 0.163844 0.066 Uiso 1 1 calc R U . . .
C5 C 0.4552(2) 0.6323(4) 0.1243(3) 0.0570(9) Uani 1 1 d . . . . .
H5 H 0.429311 0.651030 0.041485 0.068 Uiso 1 1 calc R U . . .
C6 C 0.5470(2) 0.6126(4) 0.1701(3) 0.0472(8) Uani 1 1 d . . . . .
H6 H 0.583620 0.617312 0.118570 0.057 Uiso 1 1 calc R U . . .
C7 C 0.76404(17) 0.7281(3) 0.3661(2) 0.0274(6) Uani 1 1 d . . . . .
C8 C 0.76046(18) 0.8109(3) 0.2648(2) 0.0338(7) Uani 1 1 d . . . . .
H8 H 0.725400 0.776785 0.188544 0.041 Uiso 1 1 calc R U . . .
C9 C 0.8075(2) 0.9424(3) 0.2744(3) 0.0385(7) Uani 1 1 d . . . . .
H9 H 0.804535 0.998498 0.204850 0.046 Uiso 1 1 calc R U . . .
C10 C 0.8591(2) 0.9924(3) 0.3851(3) 0.0394(7) Uani 1 1 d . . . . .
H10 H 0.891089 1.083172 0.391353 0.047 Uiso 1 1 calc R U . . .
C11 C 0.8643(2) 0.9113(3) 0.4865(3) 0.0387(7) Uani 1 1 d . . . . .
H11 H 0.900501 0.945082 0.562197 0.046 Uiso 1 1 calc R U . . .
C12 C 0.81605(18) 0.7793(3) 0.4773(2) 0.0335(7) Uani 1 1 d . . . . .
H12 H 0.818684 0.724062 0.547093 0.040 Uiso 1 1 calc R U . . .
C13 C 0.81310(17) 0.4047(3) 0.2478(2) 0.0268(6) Uani 1 1 d . . . . .
C14 C 0.81234(17) 0.3044(3) 0.1568(2) 0.0283(6) Uani 1 1 d . . . . .
C15 C 0.89178(18) 0.2492(3) 0.1460(2) 0.0333(6) Uani 1 1 d . . . . .
H15 H 0.890860 0.181611 0.083585 0.040 Uiso 1 1 calc R U . . .
C16 C 0.97312(19) 0.2917(3) 0.2256(3) 0.0397(7) Uani 1 1 d . . . . .
H16 H 1.027826 0.253354 0.217948 0.048 Uiso 1 1 calc R U . . .
C17 C 0.97437(19) 0.3902(3) 0.3165(3) 0.0402(7) Uani 1 1 d . . . . .
H17 H 1.030053 0.419514 0.371104 0.048 Uiso 1 1 calc R U . . .
C18 C 0.89455(18) 0.4461(3) 0.3279(2) 0.0343(7) Uani 1 1 d . . . . .
H18 H 0.895696 0.513053 0.390763 0.041 Uiso 1 1 calc R U . . .
N1 N 0.72825(15) 0.4562(2) 0.25215(19) 0.0331(5) Uani 1 1 d . . . . .
H1 H 0.682029 0.431869 0.190913 0.040 Uiso 1 1 calc R U . . .
O1 O 0.72663(13) 0.48814(19) 0.47796(16) 0.0363(5) Uani 1 1 d . . . . .
O2 O 0.72918(12) 0.2692(2) 0.08159(17) 0.0378(5) Uani 1 1 d . . . . .
H2A H 0.733093 0.193208 0.042133 0.057 Uiso 1 1 calc R U . . .
P1 P 0.70469(5) 0.55576(7) 0.35702(6) 0.0280(2) Uani 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
C1 C2 1.378(4) . ?
C1 C6 1.393(4) . ?
C1 P1 1.799(3) . ?
C2 C3 1.388(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.360(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.392(4) . ?
C7 C12 1.394(4) . ?
C7 P1 1.796(3) . ?
C8 C9 1.382(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.395(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.386(3) . ?
C13 C14 1.398(4) . ?
C13 N1 1.418(3) . ?
C14 O2 1.370(3) . ?
C14 C15 1.377(4) . ?
C15 C16 1.386(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
N1 P1 1.653(2) . ?
N1 H1 0.8800 . ?
O1 P1 1.4888(18) . ?
O2 H2A 0.8400 . ?

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 C1 C6 118.3(3) . . ?
C2 C1 P1 118.8(2) . . ?
C6 C1 P1 122.9(2) . . ?
C1 C2 C3 120.7(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 119.8(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.7(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C8 C7 C12 119.1(2) . . ?
C8 C7 P1 121.7(2) . . ?
C12 C7 P1 119.17(19) . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 120.1(3) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 119.7(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C7 C12 C11 120.3(3) . . ?
C7 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C18 C13 C14 119.3(2) . . ?
C18 C13 N1 124.3(2) . . ?
C14 C13 N1 116.4(2) . . ?
O2 C14 C15 124.2(2) . . ?
O2 C14 C13 115.6(2) . . ?
C15 C14 C13 120.2(2) . . ?
C14 C15 C16 120.3(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C17 C16 C15 119.8(3) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 120.2(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C13 C18 C17 120.2(3) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C13 N1 P1 128.56(18) . . ?
C13 N1 H1 115.7 . . ?
P1 N1 H1 115.7 . . ?
C14 O2 H2A 109.5 . . ?
O1 P1 N1 116.73(11) . . ?
O1 P1 C7 109.33(11) . . ?
N1 P1 C7 106.78(12) . . ?
O1 P1 C1 112.57(12) . . ?
N1 P1 C1 101.13(12) . . ?
C7 P1 C1 109.87(12) . . ?

_refine_diff_density_max         0.279
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.066



