# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_cu_mh149_0m
_database_code_depnum_ccdc_archive 'CCDC 1894569'
_audit_update_record             
;
2019-01-30 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H18 N O3 P'
_chemical_formula_weight         363.33

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   8.4621(5)
_cell_length_b                   19.7458(10)
_cell_length_c                   21.2129(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3544.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2788
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      51.17

_exptl_crystal_description       cut-plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             1520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.549
_shelx_estimated_absorpt_T_min   0.886
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6259
_exptl_absorpt_correction_T_max  0.7504
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17029
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_av_R_equivalents  0.0716
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.057
_diffrn_reflns_theta_max         52.592
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.643
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.643
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.632
_reflns_number_total             4048
_reflns_number_gt                3488
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    0.618

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0981P)²+9.0234P] 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 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.55(8)
_chemical_absolute_configuration UNK
_refine_ls_number_reflns         4048
_refine_ls_number_parameters     470
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0738
_refine_ls_wR_factor_ref         0.1949
_refine_ls_wR_factor_gt          0.1871
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
P1 P 1.1017(4) 0.51180(14) 0.52293(12) 0.0336(8) Uani 1 1 d . . . . .
O1 O 0.9928(9) 0.5650(3) 0.5462(3) 0.0349(18) Uani 1 1 d . . . . .
O2 O 0.9915(8) 0.4608(4) 0.4819(3) 0.0354(18) Uani 1 1 d . . . . .
O3 O 1.1154(11) 0.6921(4) 0.2563(3) 0.050(2) Uani 1 1 d . . . . .
N1 N 1.1898(10) 0.4674(4) 0.5776(4) 0.034(2) Uani 1 1 d . . . . .
H1A H 1.1306 0.4556 0.6099 0.041 Uiso 1 1 calc R U . . .
C1 C 1.2580(13) 0.5365(5) 0.4723(5) 0.035(3) Uani 1 1 d . . . . .
C2 C 1.4045(12) 0.5112(5) 0.4832(4) 0.030(2) Uani 1 1 d . . . . .
H2A H 1.4848 0.5252 0.4548 0.035 Uiso 1 1 calc R U . . .
C3 C 1.4530(14) 0.4660(5) 0.5320(5) 0.039(3) Uani 1 1 d . . . . .
C4 C 1.3487(13) 0.4454(5) 0.5797(5) 0.037(3) Uani 1 1 d . . . . .
C5 C 1.3982(15) 0.4028(5) 0.6284(4) 0.037(3) Uani 1 1 d . . . . .
H5A H 1.3245 0.3856 0.6581 0.044 Uiso 1 1 calc R U . . .
C6 C 1.5556(14) 0.3861(6) 0.6324(5) 0.043(3) Uani 1 1 d . . . . .
H6A H 1.5913 0.3595 0.6668 0.051 Uiso 1 1 calc R U . . .
C7 C 1.6629(15) 0.4070(6) 0.5875(5) 0.045(3) Uani 1 1 d . . . . .
H7A H 1.7706 0.3938 0.5903 0.054 Uiso 1 1 calc R U . . .
C8 C 1.6125(13) 0.4469(5) 0.5390(5) 0.038(3) Uani 1 1 d . . . . .
H8A H 1.6875 0.4623 0.5089 0.046 Uiso 1 1 calc R U . . .
C9 C 1.2222(12) 0.5795(5) 0.4173(5) 0.029(3) Uani 1 1 d . . . . .
C10 C 1.1264(16) 0.6365(6) 0.4219(5) 0.046(3) Uani 1 1 d . . . . .
H10A H 1.0843 0.6483 0.4620 0.056 Uiso 1 1 calc R U . . .
C11 C 1.0896(14) 0.6772(6) 0.3697(5) 0.042(3) Uani 1 1 d . . . . .
H11A H 1.0267 0.7168 0.3739 0.051 Uiso 1 1 calc R U . . .
C12 C 1.1485(14) 0.6573(6) 0.3121(5) 0.041(3) Uani 1 1 d . . . . .
C13 C 1.2416(13) 0.5996(5) 0.3048(5) 0.034(3) Uani 1 1 d . . . . .
H13A H 1.2791 0.5866 0.2644 0.041 Uiso 1 1 calc R U . . .
C14 C 1.2779(14) 0.5619(6) 0.3573(5) 0.038(3) Uani 1 1 d . . . . .
H14A H 1.3425 0.5229 0.3528 0.045 Uiso 1 1 calc R U . . .
C15 C 1.0221(17) 0.7508(6) 0.2604(5) 0.053(3) Uani 1 1 d . . . . .
H15A H 1.0077 0.7701 0.2182 0.080 Uiso 1 1 calc R U . . .
H15B H 1.0747 0.7841 0.2876 0.080 Uiso 1 1 calc R U . . .
H15C H 0.9187 0.7393 0.2783 0.080 Uiso 1 1 calc R U . . .
C16 C 1.0536(15) 0.3999(6) 0.4575(5) 0.042(3) Uani 1 1 d . . . . .
C17 C 1.045(2) 0.3417(6) 0.4923(6) 0.072(5) Uani 1 1 d . . . . .
H17A H 0.9954 0.3415 0.5325 0.086 Uiso 1 1 calc R U . . .
C18 C 1.111(2) 0.2825(7) 0.4670(7) 0.094(6) Uani 1 1 d . . . . .
H18A H 1.1084 0.2416 0.4907 0.113 Uiso 1 1 calc R U . . .
C19 C 1.179(2) 0.2833(8) 0.4071(8) 0.086(5) Uani 1 1 d . . . . .
H19A H 1.2267 0.2437 0.3902 0.103 Uiso 1 1 calc R U . . .
C20 C 1.1769(19) 0.3426(8) 0.3731(7) 0.074(5) Uani 1 1 d . . . . .
H20A H 1.2186 0.3432 0.3315 0.088 Uiso 1 1 calc R U . . .
C21 C 1.1164(16) 0.3999(6) 0.3979(6) 0.052(3) Uani 1 1 d . . . . .
H21A H 1.1173 0.4406 0.3739 0.062 Uiso 1 1 calc R U . . .
P1' P 0.8939(4) 0.50376(15) 0.71178(12) 0.0368(8) Uani 1 1 d . . . . .
O1' O 0.9995(8) 0.4524(3) 0.6839(3) 0.0345(18) Uani 1 1 d . . . . .
O2' O 1.0042(8) 0.5503(4) 0.7553(3) 0.0378(18) Uani 1 1 d . . . . .
O3' O 0.8916(12) 0.2976(4) 0.9583(3) 0.063(3) Uani 1 1 d . . . . .
N1' N 0.8091(10) 0.5536(5) 0.6586(4) 0.039(2) Uani 1 1 d . . . . .
H1'A H 0.8699 0.5684 0.6279 0.046 Uiso 1 1 calc R U . . .
C1' C 0.7349(12) 0.4772(5) 0.7603(4) 0.029(3) Uani 1 1 d . . . . .
C2' C 0.5897(15) 0.5046(6) 0.7525(5) 0.044(3) Uani 1 1 d . . . . .
H2'A H 0.5106 0.4923 0.7821 0.053 Uiso 1 1 calc R U . . .
C3' C 0.5437(13) 0.5521(6) 0.7022(5) 0.037(3) Uani 1 1 d . . . . .
C4' C 0.6519(12) 0.5743(5) 0.6575(5) 0.033(3) Uani 1 1 d . . . . .
C5' C 0.6034(15) 0.6156(5) 0.6073(5) 0.035(3) Uani 1 1 d . . . . .
H5'A H 0.6780 0.6301 0.5766 0.043 Uiso 1 1 calc R U . . .
C6' C 0.4445(16) 0.6354(6) 0.6023(5) 0.048(3) Uani 1 1 d . . . . .
H6'A H 0.4107 0.6630 0.5682 0.058 Uiso 1 1 calc R U . . .
C7' C 0.3365(15) 0.6141(6) 0.6481(6) 0.051(3) Uani 1 1 d . . . . .
H7'A H 0.2290 0.6277 0.6458 0.061 Uiso 1 1 calc R U . . .
C8' C 0.3879(14) 0.5726(6) 0.6974(6) 0.043(3) Uani 1 1 d . . . . .
H8'A H 0.3140 0.5582 0.7284 0.051 Uiso 1 1 calc R U . . .
C9' C 0.7712(12) 0.4276(6) 0.8110(5) 0.038(3) Uani 1 1 d . . . . .
C10' C 0.8561(14) 0.3685(5) 0.7991(5) 0.038(3) Uani 1 1 d . . . . .
H10B H 0.8865 0.3584 0.7571 0.046 Uiso 1 1 calc R U . . .
C11' C 0.8973(14) 0.3244(6) 0.8467(5) 0.043(3) Uani 1 1 d . . . . .
H11B H 0.9565 0.2847 0.8374 0.052 Uiso 1 1 calc R U . . .
C12' C 0.8524(14) 0.3379(6) 0.9075(6) 0.044(3) Uani 1 1 d . . . . .
C13' C 0.7599(14) 0.3941(6) 0.9200(5) 0.044(3) Uani 1 1 d . . . . .
H13B H 0.7234 0.4021 0.9617 0.053 Uiso 1 1 calc R U . . .
C14' C 0.7204(13) 0.4384(6) 0.8725(5) 0.040(3) Uani 1 1 d . . . . .
H14B H 0.6574 0.4769 0.8818 0.049 Uiso 1 1 calc R U . . .
C15' C 1.0152(19) 0.2470(7) 0.9469(6) 0.068(4) Uani 1 1 d . . . . .
H15D H 1.0339 0.2211 0.9857 0.102 Uiso 1 1 calc R U . . .
H15E H 1.1130 0.2699 0.9343 0.102 Uiso 1 1 calc R U . . .
H15F H 0.9813 0.2162 0.9133 0.102 Uiso 1 1 calc R U . . .
C16' C 0.9533(14) 0.6070(6) 0.7879(5) 0.045(3) Uani 1 1 d . . . . .
C17' C 0.9591(15) 0.6695(6) 0.7582(5) 0.050(3) Uani 1 1 d . . . . .
H17B H 0.9927 0.6736 0.7157 0.060 Uiso 1 1 calc R U . . .
C18' C 0.914(2) 0.7268(7) 0.7932(7) 0.074(4) Uani 1 1 d . . . . .
H18B H 0.9214 0.7705 0.7749 0.089 Uiso 1 1 calc R U . . .
C19' C 0.8585(19) 0.7201(8) 0.8531(7) 0.072(4) Uani 1 1 d . . . . .
H19B H 0.8253 0.7591 0.8757 0.087 Uiso 1 1 calc R U . . .
C20' C 0.8504(16) 0.6584(6) 0.8808(6) 0.054(4) Uani 1 1 d . . . . .
H20B H 0.8144 0.6547 0.9231 0.065 Uiso 1 1 calc R U . . .
C21' C 0.8941(17) 0.6003(7) 0.8482(6) 0.056(3) Uani 1 1 d . . . . .
H21B H 0.8834 0.5568 0.8670 0.067 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.481(7) . ?
P1 O2 1.624(7) . ?
P1 N1 1.634(8) . ?
P1 C1 1.772(10) . ?
O2 C16 1.411(13) . ?
O3 C12 1.397(13) . ?
O3 C15 1.406(14) . ?
N1 C4 1.414(13) . ?
N1 H1A 0.8800 . ?
C1 C2 1.357(15) . ?
C1 C9 1.475(14) . ?
C2 C3 1.426(14) . ?
C2 H2A 0.9500 . ?
C3 C4 1.404(15) . ?
C3 C8 1.409(16) . ?
C4 C5 1.396(15) . ?
C5 C6 1.375(16) . ?
C5 H5A 0.9500 . ?
C6 C7 1.379(16) . ?
C6 H6A 0.9500 . ?
C7 C8 1.364(15) . ?
C7 H7A 0.9500 . ?
C8 H8A 0.9500 . ?
C9 C10 1.391(15) . ?
C9 C14 1.400(14) . ?
C10 C11 1.404(15) . ?
C10 H10A 0.9500 . ?
C11 C12 1.377(15) . ?
C11 H11A 0.9500 . ?
C12 C13 1.393(15) . ?
C13 C14 1.373(14) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C21 1.373(16) . ?
C16 C17 1.367(16) . ?
C17 C18 1.403(19) . ?
C17 H17A 0.9500 . ?
C18 C19 1.40(2) . ?
C18 H18A 0.9500 . ?
C19 C20 1.38(2) . ?
C19 H19A 0.9500 . ?
C20 C21 1.349(19) . ?
C20 H20A 0.9500 . ?
C21 H21A 0.9500 . ?
P1' O1' 1.476(7) . ?
P1' O2' 1.602(8) . ?
P1' N1' 1.659(9) . ?
P1' C1' 1.773(10) . ?
O2' C16' 1.384(13) . ?
O3' C12' 1.378(14) . ?
O3' C15' 1.467(16) . ?
N1' C4' 1.393(13) . ?
N1' H1'A 0.8800 . ?
C1' C2' 1.353(15) . ?
C1' C9' 1.486(14) . ?
C2' C3' 1.473(16) . ?
C2' H2'A 0.9500 . ?
C3' C8' 1.384(16) . ?
C3' C4' 1.389(15) . ?
C4' C5' 1.402(15) . ?
C5' C6' 1.405(17) . ?
C5' H5'A 0.9500 . ?
C6' C7' 1.398(17) . ?
C6' H6'A 0.9500 . ?
C7' C8' 1.398(16) . ?
C7' H7'A 0.9500 . ?
C8' H8'A 0.9500 . ?
C9' C14' 1.389(15) . ?
C9' C10' 1.394(15) . ?
C10' C11' 1.379(15) . ?
C10' H10B 0.9500 . ?
C11' C12' 1.371(16) . ?
C11' H11B 0.9500 . ?
C12' C13' 1.384(16) . ?
C13' C14' 1.376(16) . ?
C13' H13B 0.9500 . ?
C14' H14B 0.9500 . ?
C15' H15D 0.9800 . ?
C15' H15E 0.9800 . ?
C15' H15F 0.9800 . ?
C16' C21' 1.378(16) . ?
C16' C17' 1.388(16) . ?
C17' C18' 1.406(18) . ?
C17' H17B 0.9500 . ?
C18' C19' 1.36(2) . ?
C18' H18B 0.9500 . ?
C19' C20' 1.355(18) . ?
C19' H19B 0.9500 . ?
C20' C21' 1.390(17) . ?
C20' H20B 0.9500 . ?
C21' H21B 0.9500 . ?

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 105.1(4) . . ?
O1 P1 N1 115.3(4) . . ?
O2 P1 N1 108.0(4) . . ?
O1 P1 C1 118.1(5) . . ?
O2 P1 C1 106.0(4) . . ?
N1 P1 C1 103.7(5) . . ?
C16 O2 P1 120.7(7) . . ?
C12 O3 C15 117.8(9) . . ?
C4 N1 P1 128.4(8) . . ?
C4 N1 H1A 115.8 . . ?
P1 N1 H1A 115.8 . . ?
C2 C1 C9 122.3(9) . . ?
C2 C1 P1 118.5(8) . . ?
C9 C1 P1 119.0(8) . . ?
C1 C2 C3 128.1(10) . . ?
C1 C2 H2A 115.9 . . ?
C3 C2 H2A 115.9 . . ?
C4 C3 C8 116.6(10) . . ?
C4 C3 C2 121.6(10) . . ?
C8 C3 C2 121.3(10) . . ?
C5 C4 C3 121.3(10) . . ?
C5 C4 N1 119.6(10) . . ?
C3 C4 N1 119.1(10) . . ?
C6 C5 C4 118.8(11) . . ?
C6 C5 H5A 120.6 . . ?
C4 C5 H5A 120.6 . . ?
C5 C6 C7 121.5(11) . . ?
C5 C6 H6A 119.2 . . ?
C7 C6 H6A 119.2 . . ?
C8 C7 C6 119.2(11) . . ?
C8 C7 H7A 120.4 . . ?
C6 C7 H7A 120.4 . . ?
C7 C8 C3 122.2(11) . . ?
C7 C8 H8A 118.9 . . ?
C3 C8 H8A 118.9 . . ?
C10 C9 C14 117.4(10) . . ?
C10 C9 C1 121.9(9) . . ?
C14 C9 C1 120.5(9) . . ?
C9 C10 C11 122.5(11) . . ?
C9 C10 H10A 118.8 . . ?
C11 C10 H10A 118.8 . . ?
C12 C11 C10 117.1(11) . . ?
C12 C11 H11A 121.4 . . ?
C10 C11 H11A 121.5 . . ?
C11 C12 C13 122.5(10) . . ?
C11 C12 O3 122.6(11) . . ?
C13 C12 O3 114.9(9) . . ?
C14 C13 C12 118.6(10) . . ?
C14 C13 H13A 120.7 . . ?
C12 C13 H13A 120.7 . . ?
C13 C14 C9 121.8(10) . . ?
C13 C14 H14A 119.1 . . ?
C9 C14 H14A 119.1 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 121.3(12) . . ?
C21 C16 O2 118.8(10) . . ?
C17 C16 O2 119.8(10) . . ?
C16 C17 C18 118.2(13) . . ?
C16 C17 H17A 120.9 . . ?
C18 C17 H17A 120.9 . . ?
C19 C18 C17 120.2(14) . . ?
C19 C18 H18A 119.9 . . ?
C17 C18 H18A 119.9 . . ?
C20 C19 C18 118.8(15) . . ?
C20 C19 H19A 120.6 . . ?
C18 C19 H19A 120.6 . . ?
C21 C20 C19 121.0(14) . . ?
C21 C20 H20A 119.5 . . ?
C19 C20 H20A 119.5 . . ?
C20 C21 C16 120.4(12) . . ?
C20 C21 H21A 119.8 . . ?
C16 C21 H21A 119.8 . . ?
O1' P1' O2' 105.8(4) . . ?
O1' P1' N1' 113.4(4) . . ?
O2' P1' N1' 107.7(4) . . ?
O1' P1' C1' 119.2(4) . . ?
O2' P1' C1' 106.1(4) . . ?
N1' P1' C1' 104.0(5) . . ?
C16' O2' P1' 124.8(7) . . ?
C12' O3' C15' 115.9(9) . . ?
C4' N1' P1' 126.8(8) . . ?
C4' N1' H1'A 116.6 . . ?
P1' N1' H1'A 116.6 . . ?
C2' C1' C9' 122.6(9) . . ?
C2' C1' P1' 120.0(8) . . ?
C9' C1' P1' 117.3(7) . . ?
C1' C2' C3' 125.7(10) . . ?
C1' C2' H2'A 117.2 . . ?
C3' C2' H2'A 117.2 . . ?
C8' C3' C4' 119.0(10) . . ?
C8' C3' C2' 119.4(11) . . ?
C4' C3' C2' 121.5(10) . . ?
C3' C4' N1' 121.6(9) . . ?
C3' C4' C5' 120.6(10) . . ?
N1' C4' C5' 117.6(10) . . ?
C4' C5' C6' 119.9(11) . . ?
C4' C5' H5'A 120.0 . . ?
C6' C5' H5'A 120.0 . . ?
C7' C6' C5' 119.3(10) . . ?
C7' C6' H6'A 120.3 . . ?
C5' C6' H6'A 120.3 . . ?
C6' C7' C8' 119.5(11) . . ?
C6' C7' H7'A 120.2 . . ?
C8' C7' H7'A 120.2 . . ?
C3' C8' C7' 121.5(12) . . ?
C3' C8' H8'A 119.2 . . ?
C7' C8' H8'A 119.2 . . ?
C14' C9' C10' 117.2(10) . . ?
C14' C9' C1' 121.0(10) . . ?
C10' C9' C1' 121.8(9) . . ?
C11' C10' C9' 121.8(10) . . ?
C11' C10' H10B 119.1 . . ?
C9' C10' H10B 119.1 . . ?
C12' C11' C10' 119.7(11) . . ?
C12' C11' H11B 120.1 . . ?
C10' C11' H11B 120.1 . . ?
C11' C12' O3' 123.8(11) . . ?
C11' C12' C13' 119.5(11) . . ?
O3' C12' C13' 116.7(11) . . ?
C14' C13' C12' 120.5(11) . . ?
C14' C13' H13B 119.7 . . ?
C12' C13' H13B 119.7 . . ?
C13' C14' C9' 121.0(11) . . ?
C13' C14' H14B 119.5 . . ?
C9' C14' H14B 119.5 . . ?
O3' C15' H15D 109.5 . . ?
O3' C15' H15E 109.5 . . ?
H15D C15' H15E 109.5 . . ?
O3' C15' H15F 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?
C21' C16' O2' 119.9(11) . . ?
C21' C16' C17' 121.2(12) . . ?
O2' C16' C17' 118.8(10) . . ?
C16' C17' C18' 117.8(11) . . ?
C16' C17' H17B 121.1 . . ?
C18' C17' H17B 121.1 . . ?
C19' C18' C17' 120.6(13) . . ?
C19' C18' H18B 119.7 . . ?
C17' C18' H18B 119.7 . . ?
C20' C19' C18' 120.7(14) . . ?
C20' C19' H19B 119.7 . . ?
C18' C19' H19B 119.7 . . ?
C19' C20' C21' 120.9(12) . . ?
C19' C20' H20B 119.6 . . ?
C21' C20' H20B 119.6 . . ?
C16' C21' C20' 118.6(12) . . ?
C16' C21' H21B 120.7 . . ?
C20' C21' H21B 120.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 P1 O2 C16 -173.7(7) . . . . ?
N1 P1 O2 C16 -50.0(8) . . . . ?
C1 P1 O2 C16 60.6(8) . . . . ?
O1 P1 N1 C4 -138.8(9) . . . . ?
O2 P1 N1 C4 104.1(9) . . . . ?
C1 P1 N1 C4 -8.1(11) . . . . ?
O1 P1 C1 C2 135.1(8) . . . . ?
O2 P1 C1 C2 -107.6(9) . . . . ?
N1 P1 C1 C2 6.1(10) . . . . ?
O1 P1 C1 C9 -49.6(10) . . . . ?
O2 P1 C1 C9 67.7(9) . . . . ?
N1 P1 C1 C9 -178.6(8) . . . . ?
C9 C1 C2 C3 -175.8(9) . . . . ?
P1 C1 C2 C3 -0.7(15) . . . . ?
C1 C2 C3 C4 -4.8(17) . . . . ?
C1 C2 C3 C8 -176.6(11) . . . . ?
C8 C3 C4 C5 -5.9(16) . . . . ?
C2 C3 C4 C5 -178.1(9) . . . . ?
C8 C3 C4 N1 175.4(10) . . . . ?
C2 C3 C4 N1 3.2(15) . . . . ?
P1 N1 C4 C5 -174.6(8) . . . . ?
P1 N1 C4 C3 4.1(15) . . . . ?
C3 C4 C5 C6 6.1(16) . . . . ?
N1 C4 C5 C6 -175.2(10) . . . . ?
C4 C5 C6 C7 -4.0(17) . . . . ?
C5 C6 C7 C8 1.9(17) . . . . ?
C6 C7 C8 C3 -1.9(17) . . . . ?
C4 C3 C8 C7 3.8(16) . . . . ?
C2 C3 C8 C7 176.0(9) . . . . ?
C2 C1 C9 C10 -138.5(12) . . . . ?
P1 C1 C9 C10 46.4(14) . . . . ?
C2 C1 C9 C14 44.8(15) . . . . ?
P1 C1 C9 C14 -130.3(10) . . . . ?
C14 C9 C10 C11 -2.3(17) . . . . ?
C1 C9 C10 C11 -179.1(11) . . . . ?
C9 C10 C11 C12 2.1(18) . . . . ?
C10 C11 C12 C13 -0.3(17) . . . . ?
C10 C11 C12 O3 177.5(11) . . . . ?
C15 O3 C12 C11 2.0(16) . . . . ?
C15 O3 C12 C13 -179.9(10) . . . . ?
C11 C12 C13 C14 -1.1(17) . . . . ?
O3 C12 C13 C14 -179.1(10) . . . . ?
C12 C13 C14 C9 0.9(17) . . . . ?
C10 C9 C14 C13 0.7(16) . . . . ?
C1 C9 C14 C13 177.6(10) . . . . ?
P1 O2 C16 C21 -91.9(12) . . . . ?
P1 O2 C16 C17 90.6(13) . . . . ?
C21 C16 C17 C18 4(2) . . . . ?
O2 C16 C17 C18 -178.8(14) . . . . ?
C16 C17 C18 C19 -2(3) . . . . ?
C17 C18 C19 C20 -2(3) . . . . ?
C18 C19 C20 C21 3(3) . . . . ?
C19 C20 C21 C16 -1(2) . . . . ?
C17 C16 C21 C20 -3(2) . . . . ?
O2 C16 C21 C20 179.9(12) . . . . ?
O1' P1' O2' C16' 176.7(8) . . . . ?
N1' P1' O2' C16' 55.2(9) . . . . ?
C1' P1' O2' C16' -55.7(9) . . . . ?
O1' P1' N1' C4' 136.9(9) . . . . ?
O2' P1' N1' C4' -106.4(10) . . . . ?
C1' P1' N1' C4' 5.9(11) . . . . ?
O1' P1' C1' C2' -134.8(8) . . . . ?
O2' P1' C1' C2' 106.1(9) . . . . ?
N1' P1' C1' C2' -7.4(10) . . . . ?
O1' P1' C1' C9' 48.8(9) . . . . ?
O2' P1' C1' C9' -70.3(9) . . . . ?
N1' P1' C1' C9' 176.2(8) . . . . ?
C9' C1' C2' C3' -177.8(10) . . . . ?
P1' C1' C2' C3' 6.0(15) . . . . ?
C1' C2' C3' C8' 175.6(11) . . . . ?
C1' C2' C3' C4' -1.4(17) . . . . ?
C8' C3' C4' N1' -177.8(11) . . . . ?
C2' C3' C4' N1' -0.8(16) . . . . ?
C8' C3' C4' C5' -1.7(16) . . . . ?
C2' C3' C4' C5' 175.4(9) . . . . ?
P1' N1' C4' C3' -2.4(15) . . . . ?
P1' N1' C4' C5' -178.7(7) . . . . ?
C3' C4' C5' C6' 0.8(15) . . . . ?
N1' C4' C5' C6' 177.1(10) . . . . ?
C4' C5' C6' C7' 0.6(17) . . . . ?
C5' C6' C7' C8' -1.0(17) . . . . ?
C4' C3' C8' C7' 1.2(17) . . . . ?
C2' C3' C8' C7' -175.9(10) . . . . ?
C6' C7' C8' C3' 0.1(17) . . . . ?
C2' C1' C9' C14' -45.5(16) . . . . ?
P1' C1' C9' C14' 130.8(10) . . . . ?
C2' C1' C9' C10' 134.1(12) . . . . ?
P1' C1' C9' C10' -49.6(13) . . . . ?
C14' C9' C10' C11' -4.0(17) . . . . ?
C1' C9' C10' C11' 176.4(11) . . . . ?
C9' C10' C11' C12' 0.9(18) . . . . ?
C10' C11' C12' O3' -178.3(11) . . . . ?
C10' C11' C12' C13' 3.0(18) . . . . ?
C15' O3' C12' C11' 13.5(16) . . . . ?
C15' O3' C12' C13' -167.7(11) . . . . ?
C11' C12' C13' C14' -3.7(17) . . . . ?
O3' C12' C13' C14' 177.5(10) . . . . ?
C12' C13' C14' C9' 0.4(18) . . . . ?
C10' C9' C14' C13' 3.3(17) . . . . ?
C1' C9' C14' C13' -177.1(10) . . . . ?
P1' O2' C16' C21' 88.6(12) . . . . ?
P1' O2' C16' C17' -89.6(12) . . . . ?
C21' C16' C17' C18' 4.6(19) . . . . ?
O2' C16' C17' C18' -177.2(12) . . . . ?
C16' C17' C18' C19' -3(2) . . . . ?
C17' C18' C19' C20' 2(2) . . . . ?
C18' C19' C20' C21' -2(2) . . . . ?
O2' C16' C21' C20' 177.2(11) . . . . ?
C17' C16' C21' C20' -4.6(19) . . . . ?
C19' C20' C21' C16' 3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1' 0.88 1.92 2.786(10) 166.5 .
C5 H5A O3 0.95 2.64 3.300(12) 127.3 2_765
C13 H13A O1' 0.95 2.65 3.526(13) 153.8 2_764
N1' H1'A O1 0.88 2.02 2.856(11) 157.5 .
C13' H13B O1 0.95 2.64 3.520(14) 153.9 2_665

_refine_diff_density_max         0.979
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.082

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_cu_mh228_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1894570'
_audit_update_record             
;
2019-01-30 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H23 N2 O2 P'
_chemical_formula_weight         414.42

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'

_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                   18.5757(4)
_cell_length_b                   6.1760(2)
_cell_length_c                   18.9148(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.809(2)
_cell_angle_gamma                90
_cell_volume                     2144.38(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3394
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      66.54

_exptl_crystal_description       cut-block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.324
_shelx_estimated_absorpt_T_min   0.857
_shelx_estimated_absorpt_T_max   0.925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6655
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16784
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.624
_diffrn_reflns_theta_max         66.687
_diffrn_reflns_theta_full        66.687
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3790
_reflns_number_gt                2983
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0549P)²+0.3736P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3790
_refine_ls_number_parameters     363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1093
_refine_ls_wR_factor_gt          0.0999
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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
P1 P 0.68374(2) 0.47191(8) 0.32947(3) 0.02299(15) Uani 1 1 d . . . . .
O1 O 0.71306(7) 0.6066(2) 0.40065(7) 0.0277(3) Uani 1 1 d . . . . .
O2 O 0.74064(7) 0.3233(2) 0.31228(8) 0.0300(3) Uani 1 1 d . . . . .
N1 N 0.65612(9) 0.6444(3) 0.26550(9) 0.0277(4) Uani 1 1 d . . . . .
N2 N 0.61008(11) -0.4782(3) 0.59123(11) 0.0430(5) Uani 1 1 d . . . . .
C1 C 0.60187(10) 0.3579(3) 0.35107(10) 0.0235(4) Uani 1 1 d . . . . .
C2 C 0.53774(10) 0.4433(3) 0.31978(11) 0.0251(4) Uani 1 1 d . . . . .
C3 C 0.52694(10) 0.6264(3) 0.27222(10) 0.0239(4) Uani 1 1 d . . . . .
C4 C 0.58598(10) 0.7299(3) 0.24779(10) 0.0252(4) Uani 1 1 d . . . . .
C5 C 0.57323(11) 0.9133(4) 0.20564(12) 0.0300(5) Uani 1 1 d . . . . .
C6 C 0.50335(11) 0.9950(4) 0.18814(12) 0.0305(5) Uani 1 1 d . . . . .
C7 C 0.44312(10) 0.8971(3) 0.21138(11) 0.0273(5) Uani 1 1 d . . . . .
C8 C 0.45685(10) 0.7129(3) 0.25291(11) 0.0265(4) Uani 1 1 d . . . . .
C9 C 0.60481(10) 0.1762(3) 0.40232(10) 0.0243(4) Uani 1 1 d . . . . .
C10 C 0.66106(11) 0.1568(4) 0.46033(12) 0.0336(5) Uani 1 1 d . . . . .
C11 C 0.66176(12) -0.0094(4) 0.50910(12) 0.0355(5) Uani 1 1 d . . . . .
C12 C 0.60619(11) -0.1624(3) 0.50112(11) 0.0287(5) Uani 1 1 d . . . . .
C13 C 0.54935(12) -0.1449(4) 0.44391(12) 0.0315(5) Uani 1 1 d . . . . .
C14 C 0.54962(11) 0.0212(3) 0.39534(11) 0.0290(5) Uani 1 1 d . . . . .
C15 C 0.60783(11) -0.3384(4) 0.55128(12) 0.0331(5) Uani 1 1 d . . . . .
C16 C 0.36509(11) 0.9838(4) 0.19309(12) 0.0327(5) Uani 1 1 d . . . . .
C17 C 0.33418(15) 1.0271(6) 0.26286(16) 0.0537(8) Uani 1 1 d . . . . .
C18 C 0.31758(13) 0.8134(4) 0.14931(15) 0.0407(6) Uani 1 1 d . . . . .
C19 C 0.36154(14) 1.1938(4) 0.15044(17) 0.0438(6) Uani 1 1 d . . . . .
C20 C 0.78657(10) 0.6703(4) 0.41712(11) 0.0280(5) Uani 1 1 d . . . . .
C21 C 0.80745(13) 0.8682(4) 0.39446(13) 0.0386(6) Uani 1 1 d . . . . .
C22 C 0.87985(14) 0.9322(4) 0.41409(16) 0.0477(7) Uani 1 1 d . . . . .
C23 C 0.92857(14) 0.7981(5) 0.45504(14) 0.0469(7) Uani 1 1 d . . . . .
C24 C 0.90635(13) 0.6005(5) 0.47699(14) 0.0472(6) Uani 1 1 d . . . . .
C25 C 0.83479(12) 0.5345(4) 0.45756(13) 0.0395(6) Uani 1 1 d . . . . .
H1N H 0.6854(13) 0.699(4) 0.2434(13) 0.035(7) Uiso 1 1 d . . . . .
H2 H 0.4938(11) 0.373(3) 0.3322(11) 0.023(5) Uiso 1 1 d . . . . .
H5 H 0.6129(12) 0.991(4) 0.1885(11) 0.029(6) Uiso 1 1 d . . . . .
H6 H 0.4965(12) 1.124(4) 0.1602(13) 0.042(7) Uiso 1 1 d . . . . .
H8 H 0.4180(11) 0.642(3) 0.2724(10) 0.019(5) Uiso 1 1 d . . . . .
H10 H 0.7008(12) 0.268(4) 0.4660(12) 0.034(6) Uiso 1 1 d . . . . .
H11 H 0.6972(15) -0.014(5) 0.5499(15) 0.058(8) Uiso 1 1 d . . . . .
H13 H 0.5140(12) -0.254(4) 0.4406(12) 0.031(6) Uiso 1 1 d . . . . .
H14 H 0.5132(12) 0.035(4) 0.3555(12) 0.033(6) Uiso 1 1 d . . . . .
H17A H 0.3625(15) 1.144(5) 0.2909(16) 0.062(9) Uiso 1 1 d . . . . .
H17B H 0.3392(12) 0.891(4) 0.2961(13) 0.038(7) Uiso 1 1 d . . . . .
H17C H 0.2838(15) 1.073(5) 0.2501(15) 0.059(8) Uiso 1 1 d . . . . .
H18A H 0.3366(14) 0.782(4) 0.1058(15) 0.049(8) Uiso 1 1 d . . . . .
H18B H 0.2699(15) 0.873(5) 0.1381(15) 0.058(8) Uiso 1 1 d . . . . .
H18C H 0.3152(14) 0.682(5) 0.1773(15) 0.055(8) Uiso 1 1 d . . . . .
H19A H 0.3129(15) 1.236(4) 0.1405(14) 0.051(8) Uiso 1 1 d . . . . .
H19B H 0.3812(14) 1.183(4) 0.1060(16) 0.051(8) Uiso 1 1 d . . . . .
H19C H 0.3935(15) 1.307(5) 0.1772(15) 0.062(9) Uiso 1 1 d . . . . .
H21 H 0.7695(14) 0.965(4) 0.3689(14) 0.048(7) Uiso 1 1 d . . . . .
H22 H 0.8957(14) 1.059(5) 0.3988(15) 0.057(8) Uiso 1 1 d . . . . .
H23 H 0.9792(15) 0.849(5) 0.4696(14) 0.062(9) Uiso 1 1 d . . . . .
H24 H 0.9397(15) 0.498(5) 0.5056(15) 0.063(9) Uiso 1 1 d . . . . .
H25 H 0.8179(13) 0.390(5) 0.4731(14) 0.052(8) 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
P1 O2 1.4731(14) . ?
P1 O1 1.6051(14) . ?
P1 N1 1.6347(18) . ?
P1 C1 1.7792(19) . ?
O1 C20 1.409(2) . ?
N1 C4 1.398(2) . ?
N1 H1N 0.81(2) . ?
N2 C15 1.144(3) . ?
C1 C2 1.353(3) . ?
C1 C9 1.479(3) . ?
C2 C3 1.440(3) . ?
C2 H2 0.98(2) . ?
C3 C8 1.403(3) . ?
C3 C4 1.407(3) . ?
C4 C5 1.385(3) . ?
C5 C6 1.385(3) . ?
C5 H5 0.97(2) . ?
C6 C7 1.401(3) . ?
C6 H6 0.96(3) . ?
C7 C8 1.384(3) . ?
C7 C16 1.534(3) . ?
C8 H8 0.97(2) . ?
C9 C14 1.394(3) . ?
C9 C10 1.400(3) . ?
C10 C11 1.379(3) . ?
C10 H10 1.00(2) . ?
C11 C12 1.390(3) . ?
C11 H11 0.93(3) . ?
C12 C13 1.395(3) . ?
C12 C15 1.440(3) . ?
C13 C14 1.377(3) . ?
C13 H13 0.94(2) . ?
C14 H14 0.94(2) . ?
C16 C19 1.524(3) . ?
C16 C18 1.532(3) . ?
C16 C17 1.541(3) . ?
C17 H17A 1.00(3) . ?
C17 H17B 1.05(3) . ?
C17 H17C 0.97(3) . ?
C18 H18A 0.96(3) . ?
C18 H18B 0.95(3) . ?
C18 H18C 0.97(3) . ?
C19 H19A 0.93(3) . ?
C19 H19B 0.97(3) . ?
C19 H19C 1.00(3) . ?
C20 C21 1.371(3) . ?
C20 C25 1.371(3) . ?
C21 C22 1.396(3) . ?
C21 H21 0.99(3) . ?
C22 C23 1.375(4) . ?
C22 H22 0.90(3) . ?
C23 C24 1.373(4) . ?
C23 H23 0.99(3) . ?
C24 C25 1.385(3) . ?
C24 H24 0.99(3) . ?
C25 H25 1.00(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
O2 P1 O1 110.19(8) . . ?
O2 P1 N1 113.40(9) . . ?
O1 P1 N1 108.11(9) . . ?
O2 P1 C1 118.14(9) . . ?
O1 P1 C1 101.80(8) . . ?
N1 P1 C1 104.21(9) . . ?
C20 O1 P1 121.52(12) . . ?
C4 N1 P1 126.77(14) . . ?
C4 N1 H1N 113.4(17) . . ?
P1 N1 H1N 119.5(17) . . ?
C2 C1 C9 121.61(17) . . ?
C2 C1 P1 118.14(16) . . ?
C9 C1 P1 120.25(14) . . ?
C1 C2 C3 127.46(18) . . ?
C1 C2 H2 115.6(12) . . ?
C3 C2 H2 116.9(12) . . ?
C8 C3 C4 118.69(19) . . ?
C8 C3 C2 119.80(18) . . ?
C4 C3 C2 121.40(17) . . ?
C5 C4 N1 121.18(18) . . ?
C5 C4 C3 119.18(18) . . ?
N1 C4 C3 119.63(19) . . ?
C6 C5 C4 120.48(19) . . ?
C6 C5 H5 118.1(13) . . ?
C4 C5 H5 121.4(13) . . ?
C5 C6 C7 122.2(2) . . ?
C5 C6 H6 118.5(14) . . ?
C7 C6 H6 119.3(14) . . ?
C8 C7 C6 116.53(18) . . ?
C8 C7 C16 120.03(18) . . ?
C6 C7 C16 123.45(19) . . ?
C7 C8 C3 122.96(19) . . ?
C7 C8 H8 120.6(12) . . ?
C3 C8 H8 116.4(12) . . ?
C14 C9 C10 117.74(19) . . ?
C14 C9 C1 120.42(18) . . ?
C10 C9 C1 121.81(18) . . ?
C11 C10 C9 121.2(2) . . ?
C11 C10 H10 120.5(13) . . ?
C9 C10 H10 118.3(13) . . ?
C10 C11 C12 120.2(2) . . ?
C10 C11 H11 120.6(18) . . ?
C12 C11 H11 119.1(18) . . ?
C11 C12 C13 119.5(2) . . ?
C11 C12 C15 120.1(2) . . ?
C13 C12 C15 120.4(2) . . ?
C14 C13 C12 119.7(2) . . ?
C14 C13 H13 124.5(14) . . ?
C12 C13 H13 115.8(14) . . ?
C13 C14 C9 121.7(2) . . ?
C13 C14 H14 121.8(14) . . ?
C9 C14 H14 116.4(14) . . ?
N2 C15 C12 179.1(2) . . ?
C19 C16 C18 108.9(2) . . ?
C19 C16 C7 112.29(19) . . ?
C18 C16 C7 109.17(18) . . ?
C19 C16 C17 108.3(2) . . ?
C18 C16 C17 108.8(2) . . ?
C7 C16 C17 109.31(19) . . ?
C16 C17 H17A 110.2(17) . . ?
C16 C17 H17B 111.4(14) . . ?
H17A C17 H17B 106(2) . . ?
C16 C17 H17C 108.0(17) . . ?
H17A C17 H17C 109(2) . . ?
H17B C17 H17C 112(2) . . ?
C16 C18 H18A 110.0(16) . . ?
C16 C18 H18B 107.1(17) . . ?
H18A C18 H18B 110(2) . . ?
C16 C18 H18C 110.3(16) . . ?
H18A C18 H18C 111(2) . . ?
H18B C18 H18C 109(2) . . ?
C16 C19 H19A 107.9(17) . . ?
C16 C19 H19B 114.0(16) . . ?
H19A C19 H19B 109(2) . . ?
C16 C19 H19C 110.7(16) . . ?
H19A C19 H19C 113(2) . . ?
H19B C19 H19C 102(2) . . ?
C21 C20 C25 121.8(2) . . ?
C21 C20 O1 119.39(19) . . ?
C25 C20 O1 118.73(19) . . ?
C20 C21 C22 118.5(2) . . ?
C20 C21 H21 118.5(15) . . ?
C22 C21 H21 122.8(15) . . ?
C23 C22 C21 120.2(2) . . ?
C23 C22 H22 119.0(18) . . ?
C21 C22 H22 120.7(18) . . ?
C24 C23 C22 120.2(2) . . ?
C24 C23 H23 121.0(17) . . ?
C22 C23 H23 118.7(17) . . ?
C23 C24 C25 120.1(2) . . ?
C23 C24 H24 122.9(17) . . ?
C25 C24 H24 117.0(17) . . ?
C20 C25 C24 119.1(2) . . ?
C20 C25 H25 120.0(14) . . ?
C24 C25 H25 120.9(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 P1 O1 C20 34.23(17) . . . . ?
N1 P1 O1 C20 -90.20(16) . . . . ?
C1 P1 O1 C20 160.40(15) . . . . ?
O2 P1 N1 C4 147.27(17) . . . . ?
O1 P1 N1 C4 -90.25(19) . . . . ?
C1 P1 N1 C4 17.5(2) . . . . ?
O2 P1 C1 C2 -133.68(16) . . . . ?
O1 P1 C1 C2 105.55(17) . . . . ?
N1 P1 C1 C2 -6.81(19) . . . . ?
O2 P1 C1 C9 46.79(18) . . . . ?
O1 P1 C1 C9 -73.98(17) . . . . ?
N1 P1 C1 C9 173.66(16) . . . . ?
C9 C1 C2 C3 176.41(19) . . . . ?
P1 C1 C2 C3 -3.1(3) . . . . ?
C1 C2 C3 C8 -170.6(2) . . . . ?
C1 C2 C3 C4 5.4(3) . . . . ?
P1 N1 C4 C5 163.21(17) . . . . ?
P1 N1 C4 C3 -17.7(3) . . . . ?
C8 C3 C4 C5 0.0(3) . . . . ?
C2 C3 C4 C5 -176.09(19) . . . . ?
C8 C3 C4 N1 -179.02(18) . . . . ?
C2 C3 C4 N1 4.8(3) . . . . ?
N1 C4 C5 C6 179.5(2) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C5 C6 C7 C16 179.8(2) . . . . ?
C6 C7 C8 C3 0.7(3) . . . . ?
C16 C7 C8 C3 -179.31(19) . . . . ?
C4 C3 C8 C7 -0.6(3) . . . . ?
C2 C3 C8 C7 175.57(19) . . . . ?
C2 C1 C9 C14 31.7(3) . . . . ?
P1 C1 C9 C14 -148.77(16) . . . . ?
C2 C1 C9 C10 -146.2(2) . . . . ?
P1 C1 C9 C10 33.3(3) . . . . ?
C14 C9 C10 C11 -0.2(3) . . . . ?
C1 C9 C10 C11 177.7(2) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C10 C11 C12 C13 -0.8(3) . . . . ?
C10 C11 C12 C15 178.7(2) . . . . ?
C11 C12 C13 C14 1.2(3) . . . . ?
C15 C12 C13 C14 -178.3(2) . . . . ?
C12 C13 C14 C9 -1.2(3) . . . . ?
C10 C9 C14 C13 0.7(3) . . . . ?
C1 C9 C14 C13 -177.31(19) . . . . ?
C8 C7 C16 C19 176.9(2) . . . . ?
C6 C7 C16 C19 -3.1(3) . . . . ?
C8 C7 C16 C18 -62.2(3) . . . . ?
C6 C7 C16 C18 117.8(2) . . . . ?
C8 C7 C16 C17 56.7(3) . . . . ?
C6 C7 C16 C17 -123.3(3) . . . . ?
P1 O1 C20 C21 91.5(2) . . . . ?
P1 O1 C20 C25 -90.7(2) . . . . ?
C25 C20 C21 C22 -0.6(4) . . . . ?
O1 C20 C21 C22 177.2(2) . . . . ?
C20 C21 C22 C23 0.2(4) . . . . ?
C21 C22 C23 C24 -0.1(4) . . . . ?
C22 C23 C24 C25 0.4(4) . . . . ?
C21 C20 C25 C24 1.0(4) . . . . ?
O1 C20 C25 C24 -176.8(2) . . . . ?
C23 C24 C25 C20 -0.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O2 0.81(2) 2.01(3) 2.815(2) 178(2) 2_655
C2 H2 N2 0.98(2) 2.66(2) 3.440(3) 136.1(16) 3_656
C21 H21 O2 0.99(3) 2.48(3) 3.357(3) 147(2) 1_565

_refine_diff_density_max         0.352
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.046



####################################################################### 
# 
# 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_mhr257c_a
_database_code_depnum_ccdc_archive 'CCDC 1894572'
_audit_update_record             
;
2019-01-30 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22.50 H14.50 Cl1.50 F3 N2 O2 P'
_chemical_formula_weight         486.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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                   29.394(3)
_cell_length_b                   6.3419(5)
_cell_length_c                   28.119(3)
_cell_angle_alpha                90
_cell_angle_beta                 121.188(4)
_cell_angle_gamma                90
_cell_volume                     4484.3(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5952
_cell_measurement_theta_min      3.53
_cell_measurement_theta_max      66.09

_exptl_crystal_description       cut-prizm
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_F_000             1976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    3.161
_shelx_estimated_absorpt_T_min   0.648
_shelx_estimated_absorpt_T_max   0.884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5167
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13891
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.515
_diffrn_reflns_theta_max         66.972
_diffrn_reflns_theta_full        66.972
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measured_fraction_theta_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_point_group_measured_fraction_full 0.955
_reflns_number_total             3815
_reflns_number_gt                2947
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1083P)²+19.0782P] 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         3815
_refine_ls_number_parameters     302
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1045
_refine_ls_R_factor_gt           0.0849
_refine_ls_wR_factor_ref         0.2386
_refine_ls_wR_factor_gt          0.2236
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.087
_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
P1 P 0.67320(4) 0.56095(19) 0.68135(4) 0.0425(4) Uani 1 1 d . . . . .
O1 O 0.70287(11) 0.7067(5) 0.72826(11) 0.0511(8) Uani 1 1 d . . . . .
O2 O 0.62906(11) 0.4369(5) 0.68703(11) 0.0525(9) Uani 1 1 d . . . . .
N1 N 0.71138(14) 0.3887(6) 0.67631(13) 0.0473(10) Uani 1 1 d D . . . .
N2 N 0.4663(2) 1.4974(9) 0.5611(2) 0.0843(16) Uani 1 1 d . . . . .
F1 F 0.6643(2) 0.1654(8) 0.43571(14) 0.1262(18) Uani 1 1 d . . . . .
F2 F 0.72987(18) -0.0215(8) 0.48243(17) 0.1136(15) Uani 1 1 d . . . . .
F3 F 0.6564(2) -0.1319(9) 0.46416(19) 0.146(2) Uani 1 1 d . . . . .
C1 C 0.63499(15) 0.6694(7) 0.61320(16) 0.0421(10) Uani 1 1 d . . . . .
C2 C 0.63944(16) 0.5790(7) 0.57235(16) 0.0423(10) Uani 1 1 d . . . . .
H2A H 0.6196 0.6429 0.5367 0.051 Uiso 1 1 calc R U . . .
C3 C 0.67040(16) 0.3984(7) 0.57621(16) 0.0408(10) Uani 1 1 d . . . . .
C4 C 0.70505(16) 0.3009(7) 0.62762(16) 0.0434(10) Uani 1 1 d . . . . .
C5 C 0.73298(18) 0.1208(8) 0.62941(18) 0.0511(12) Uani 1 1 d . . . . .
H5A H 0.7563 0.0549 0.6641 0.061 Uiso 1 1 calc R U . . .
C6 C 0.72711(19) 0.0382(9) 0.58173(19) 0.0563(12) Uani 1 1 d . . . . .
H6A H 0.7462 -0.0848 0.5832 0.068 Uiso 1 1 calc R U . . .
C7 C 0.69265(19) 0.1357(9) 0.53035(18) 0.0532(12) Uani 1 1 d . . . . .
C8 C 0.66562(18) 0.3121(8) 0.52807(18) 0.0498(11) Uani 1 1 d . . . . .
H8A H 0.6431 0.3783 0.4932 0.060 Uiso 1 1 calc R U . . .
C9 C 0.6856(3) 0.0359(11) 0.4788(2) 0.0733(17) Uani 1 1 d . . . . .
C10 C 0.59912(16) 0.8511(7) 0.60285(16) 0.0440(11) Uani 1 1 d . . . . .
C11 C 0.58735(19) 0.9919(8) 0.5607(2) 0.0542(12) Uani 1 1 d . . . . .
H11A H 0.6035 0.9745 0.5391 0.065 Uiso 1 1 calc R U . . .
C12 C 0.55266(19) 1.1578(8) 0.5490(2) 0.0582(14) Uani 1 1 d . . . . .
H12A H 0.5447 1.2513 0.5193 0.070 Uiso 1 1 calc R U . . .
C13 C 0.52989(17) 1.1875(8) 0.58023(19) 0.0546(13) Uani 1 1 d . . . . .
C14 C 0.5407(2) 1.0473(10) 0.6225(2) 0.0741(17) Uani 1 1 d . . . . .
H14A H 0.5244 1.0655 0.6439 0.089 Uiso 1 1 calc R U . . .
C15 C 0.5752(2) 0.8803(10) 0.6336(2) 0.0654(15) Uani 1 1 d . . . . .
H15A H 0.5825 0.7847 0.6627 0.079 Uiso 1 1 calc R U . . .
C16 C 0.4943(2) 1.3614(10) 0.5694(2) 0.0675(15) Uani 1 1 d . . . . .
C17 C 0.63836(18) 0.3644(9) 0.73857(18) 0.0529(12) Uani 1 1 d . . . . .
C18 C 0.6228(2) 0.4906(12) 0.7676(3) 0.0791(18) Uani 1 1 d . . . . .
H18A H 0.6074 0.6250 0.7536 0.095 Uiso 1 1 calc R U . . .
C19 C 0.6301(3) 0.4180(16) 0.8177(3) 0.104(3) Uani 1 1 d . . . . .
H19A H 0.6205 0.5039 0.8388 0.124 Uiso 1 1 calc R U . . .
C20 C 0.6513(3) 0.2218(16) 0.8366(3) 0.100(3) Uani 1 1 d . . . . .
H20A H 0.6546 0.1690 0.8698 0.120 Uiso 1 1 calc R U . . .
C21 C 0.6678(2) 0.1014(12) 0.8082(3) 0.083(2) Uani 1 1 d . . . . .
H21A H 0.6839 -0.0319 0.8226 0.099 Uiso 1 1 calc R U . . .
C22 C 0.6613(2) 0.1730(9) 0.7580(2) 0.0640(14) Uani 1 1 d . . . . .
H22A H 0.6727 0.0897 0.7380 0.077 Uiso 1 1 calc R U . . .
H1N H 0.7405(13) 0.321(7) 0.7095(13) 0.050(12) Uiso 1 1 d D . . . .
Cl1S Cl 0.4815(2) 0.7492(8) 0.6914(2) 0.238(2) Uani 1 1 d D . . . .
Cl2S Cl 0.5179(4) 1.1154(16) 0.7504(5) 0.247(5) Uani 0.5 1 d D . P . .
C1S C 0.4791(6) 0.895(2) 0.7424(7) 0.115(6) Uani 0.5 1 d D . P . .


_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 1.471(3) . ?
P1 O2 1.594(3) . ?
P1 N1 1.624(4) . ?
P1 C1 1.783(4) . ?
O2 C17 1.406(5) . ?
N1 C4 1.398(5) . ?
N1 H1N 0.980(19) . ?
N2 C16 1.130(7) . ?
F1 C9 1.322(7) . ?
F2 C9 1.304(7) . ?
F3 C9 1.293(8) . ?
C1 C2 1.349(6) . ?
C1 C10 1.485(6) . ?
C2 C3 1.432(6) . ?
C2 H2A 0.9500 . ?
C3 C8 1.398(6) . ?
C3 C4 1.408(6) . ?
C4 C5 1.392(7) . ?
C5 C6 1.365(7) . ?
C5 H5A 0.9500 . ?
C6 C7 1.407(7) . ?
C6 H6A 0.9500 . ?
C7 C8 1.354(7) . ?
C7 C9 1.494(7) . ?
C8 H8A 0.9500 . ?
C10 C11 1.378(6) . ?
C10 C15 1.381(7) . ?
C11 C12 1.381(7) . ?
C11 H11A 0.9500 . ?
C12 C13 1.364(8) . ?
C12 H12A 0.9500 . ?
C13 C14 1.384(7) . ?
C13 C16 1.440(8) . ?
C14 C15 1.386(8) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C17 C22 1.359(8) . ?
C17 C18 1.379(8) . ?
C18 C19 1.388(9) . ?
C18 H18A 0.9500 . ?
C19 C20 1.369(12) . ?
C19 H19A 0.9500 . ?
C20 C21 1.362(11) . ?
C20 H20A 0.9500 . ?
C21 C22 1.397(8) . ?
C21 H21A 0.9500 . ?
C22 H22A 0.9500 . ?
Cl1S C1S 1.737(15) . ?
Cl1S C1S 1.849(19) 2_656 ?
Cl2S Cl2S 1.039(14) 2_656 ?
Cl2S C1S 1.411(15) 2_656 ?
Cl2S C1S 1.745(14) . ?
C1S C1S 1.07(3) 2_656 ?
C1S Cl2S 1.411(15) 2_656 ?
C1S Cl1S 1.849(19) 2_656 ?

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 110.83(19) . . ?
O1 P1 N1 112.67(18) . . ?
O2 P1 N1 108.2(2) . . ?
O1 P1 C1 118.2(2) . . ?
O2 P1 C1 101.87(17) . . ?
N1 P1 C1 104.2(2) . . ?
C17 O2 P1 122.1(3) . . ?
C4 N1 P1 127.3(3) . . ?
C4 N1 H1N 112(3) . . ?
P1 N1 H1N 121(3) . . ?
C2 C1 C10 122.3(4) . . ?
C2 C1 P1 117.8(3) . . ?
C10 C1 P1 119.9(3) . . ?
C1 C2 C3 127.8(4) . . ?
C1 C2 H2A 116.1 . . ?
C3 C2 H2A 116.1 . . ?
C8 C3 C4 118.6(4) . . ?
C8 C3 C2 119.9(4) . . ?
C4 C3 C2 121.5(4) . . ?
C5 C4 N1 120.9(4) . . ?
C5 C4 C3 119.8(4) . . ?
N1 C4 C3 119.3(4) . . ?
C6 C5 C4 120.5(4) . . ?
C6 C5 H5A 119.8 . . ?
C4 C5 H5A 119.8 . . ?
C5 C6 C7 119.9(5) . . ?
C5 C6 H6A 120.1 . . ?
C7 C6 H6A 120.1 . . ?
C8 C7 C6 120.3(4) . . ?
C8 C7 C9 121.4(5) . . ?
C6 C7 C9 118.3(5) . . ?
C7 C8 C3 121.0(4) . . ?
C7 C8 H8A 119.5 . . ?
C3 C8 H8A 119.5 . . ?
F3 C9 F2 105.4(6) . . ?
F3 C9 F1 107.4(6) . . ?
F2 C9 F1 102.9(5) . . ?
F3 C9 C7 113.2(5) . . ?
F2 C9 C7 114.3(5) . . ?
F1 C9 C7 112.9(5) . . ?
C11 C10 C15 118.0(5) . . ?
C11 C10 C1 120.5(4) . . ?
C15 C10 C1 121.4(4) . . ?
C10 C11 C12 121.5(5) . . ?
C10 C11 H11A 119.2 . . ?
C12 C11 H11A 119.2 . . ?
C13 C12 C11 120.1(5) . . ?
C13 C12 H12A 120.0 . . ?
C11 C12 H12A 120.0 . . ?
C12 C13 C14 119.6(5) . . ?
C12 C13 C16 120.9(5) . . ?
C14 C13 C16 119.5(5) . . ?
C13 C14 C15 119.9(5) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C10 C15 C14 120.8(5) . . ?
C10 C15 H15A 119.6 . . ?
C14 C15 H15A 119.6 . . ?
N2 C16 C13 179.5(7) . . ?
C22 C17 C18 121.8(5) . . ?
C22 C17 O2 119.9(5) . . ?
C18 C17 O2 118.3(5) . . ?
C17 C18 C19 118.9(7) . . ?
C17 C18 H18A 120.5 . . ?
C19 C18 H18A 120.5 . . ?
C20 C19 C18 119.7(7) . . ?
C20 C19 H19A 120.2 . . ?
C18 C19 H19A 120.2 . . ?
C21 C20 C19 120.7(6) . . ?
C21 C20 H20A 119.6 . . ?
C19 C20 H20A 119.6 . . ?
C20 C21 C22 120.4(6) . . ?
C20 C21 H21A 119.8 . . ?
C22 C21 H21A 119.8 . . ?
C17 C22 C21 118.4(6) . . ?
C17 C22 H22A 120.8 . . ?
C21 C22 H22A 120.8 . . ?
C1S Cl1S C1S 34.6(9) . 2_656 ?
Cl2S Cl2S C1S 89.5(7) 2_656 2_656 ?
Cl2S Cl2S C1S 54.0(6) 2_656 . ?
C1S Cl2S C1S 37.9(11) 2_656 . ?
C1S C1S Cl2S 88.2(8) 2_656 2_656 ?
C1S C1S Cl1S 78.4(16) 2_656 . ?
Cl2S C1S Cl1S 128.2(13) 2_656 . ?
C1S C1S Cl2S 53.9(6) 2_656 . ?
Cl2S C1S Cl2S 36.5(7) 2_656 . ?
Cl1S C1S Cl2S 103.2(9) . . ?
C1S C1S Cl1S 67.0(15) 2_656 2_656 ?
Cl2S C1S Cl1S 113.0(11) 2_656 2_656 ?
Cl1S C1S Cl1S 107.1(9) . 2_656 ?
Cl2S C1S Cl1S 104.1(9) . 2_656 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 P1 O2 C17 -38.9(4) . . . . ?
N1 P1 O2 C17 85.0(4) . . . . ?
C1 P1 O2 C17 -165.5(4) . . . . ?
O1 P1 N1 C4 -146.4(4) . . . . ?
O2 P1 N1 C4 90.8(4) . . . . ?
C1 P1 N1 C4 -17.0(4) . . . . ?
O1 P1 C1 C2 133.5(3) . . . . ?
O2 P1 C1 C2 -104.9(4) . . . . ?
N1 P1 C1 C2 7.6(4) . . . . ?
O1 P1 C1 C10 -47.5(4) . . . . ?
O2 P1 C1 C10 74.1(3) . . . . ?
N1 P1 C1 C10 -173.4(3) . . . . ?
C10 C1 C2 C3 -176.8(4) . . . . ?
P1 C1 C2 C3 2.2(6) . . . . ?
C1 C2 C3 C8 172.8(4) . . . . ?
C1 C2 C3 C4 -5.7(7) . . . . ?
P1 N1 C4 C5 -164.7(4) . . . . ?
P1 N1 C4 C3 16.1(6) . . . . ?
C8 C3 C4 C5 -0.9(6) . . . . ?
C2 C3 C4 C5 177.6(4) . . . . ?
C8 C3 C4 N1 178.2(4) . . . . ?
C2 C3 C4 N1 -3.2(6) . . . . ?
N1 C4 C5 C6 -179.0(4) . . . . ?
C3 C4 C5 C6 0.1(7) . . . . ?
C4 C5 C6 C7 0.1(8) . . . . ?
C5 C6 C7 C8 0.6(8) . . . . ?
C5 C6 C7 C9 -177.6(5) . . . . ?
C6 C7 C8 C3 -1.4(7) . . . . ?
C9 C7 C8 C3 176.7(5) . . . . ?
C4 C3 C8 C7 1.6(7) . . . . ?
C2 C3 C8 C7 -177.0(4) . . . . ?
C8 C7 C9 F3 -103.6(7) . . . . ?
C6 C7 C9 F3 74.5(7) . . . . ?
C8 C7 C9 F2 135.8(6) . . . . ?
C6 C7 C9 F2 -46.1(8) . . . . ?
C8 C7 C9 F1 18.6(8) . . . . ?
C6 C7 C9 F1 -163.2(5) . . . . ?
C2 C1 C10 C11 -29.0(6) . . . . ?
P1 C1 C10 C11 152.1(3) . . . . ?
C2 C1 C10 C15 148.8(5) . . . . ?
P1 C1 C10 C15 -30.2(6) . . . . ?
C15 C10 C11 C12 -0.1(7) . . . . ?
C1 C10 C11 C12 177.7(4) . . . . ?
C10 C11 C12 C13 1.2(7) . . . . ?
C11 C12 C13 C14 -1.7(7) . . . . ?
C11 C12 C13 C16 178.9(4) . . . . ?
C12 C13 C14 C15 1.2(8) . . . . ?
C16 C13 C14 C15 -179.5(5) . . . . ?
C11 C10 C15 C14 -0.4(8) . . . . ?
C1 C10 C15 C14 -178.2(5) . . . . ?
C13 C14 C15 C10 -0.1(9) . . . . ?
P1 O2 C17 C22 -86.6(5) . . . . ?
P1 O2 C17 C18 94.4(5) . . . . ?
C22 C17 C18 C19 -1.1(9) . . . . ?
O2 C17 C18 C19 177.9(6) . . . . ?
C17 C18 C19 C20 -1.5(11) . . . . ?
C18 C19 C20 C21 3.4(11) . . . . ?
C19 C20 C21 C22 -2.7(11) . . . . ?
C18 C17 C22 C21 1.8(8) . . . . ?
O2 C17 C22 C21 -177.1(5) . . . . ?
C20 C21 C22 C17 0.1(9) . . . . ?
C1S Cl1S C1S Cl2S 78.4(14) 2_656 . . 2_656 ?
C1S Cl1S C1S Cl2S 48.3(9) 2_656 . . . ?
C1S Cl1S C1S Cl1S -61.3(11) 2_656 . . 2_656 ?
Cl2S Cl2S C1S C1S -157(3) 2_656 . . 2_656 ?
C1S Cl2S C1S Cl2S 157(3) 2_656 . . 2_656 ?
Cl2S Cl2S C1S Cl1S 138.5(18) 2_656 . . . ?
C1S Cl2S C1S Cl1S -64.8(17) 2_656 . . . ?
Cl2S Cl2S C1S Cl1S -109.7(17) 2_656 . . 2_656 ?
C1S Cl2S C1S Cl1S 47.0(17) 2_656 . . 2_656 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C22 H22A O1 0.95 2.65 3.463(7) 144.1 1_545
N1 H1N O1 0.980(19) 1.83(2) 2.807(4) 177(4) 4_646

_refine_diff_density_max         0.560
_refine_diff_density_min         -0.788
_refine_diff_density_rms         0.077



####################################################################### 
# 
# 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_mo_mh150_0m
_database_code_depnum_ccdc_archive 'CCDC 1894573'
_audit_update_record             
;
2019-01-30 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H15 N2 O2 P'
_chemical_formula_weight         358.32

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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                   24.331(4)
_cell_length_b                   10.2408(18)
_cell_length_c                   14.540(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.686(3)
_cell_angle_gamma                90
_cell_volume                     3534.7(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2903
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      26.34

_exptl_crystal_description       cut-block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.173
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7054
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube with triumph'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11395
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.716
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.972
_reflns_number_total             3113
_reflns_number_gt                2404
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_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)+(0.0612P)²+0.9389P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3113
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.1104
_refine_ls_wR_factor_gt          0.0955
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
P1 P 0.01873(2) 0.79778(5) 0.03851(4) 0.02689(18) Uani 1 1 d . . . . .
O1 O 0.05084(5) 0.90993(12) 0.08829(10) 0.0310(4) Uani 1 1 d . . . . .
O2 O 0.04941(5) 0.74432(13) -0.04177(10) 0.0321(4) Uani 1 1 d . . . . .
N1 N -0.04631(7) 0.83800(18) -0.01088(13) 0.0333(4) Uani 1 1 d . . . . .
N2 N 0.26080(9) 0.3644(2) 0.33052(16) 0.0566(6) Uani 1 1 d . . . . .
C1 C 0.01190(8) 0.65157(18) 0.10097(13) 0.0268(5) Uani 1 1 d . . . . .
C2 C -0.04025(8) 0.5973(2) 0.09017(15) 0.0304(5) Uani 1 1 d . . . . .
C3 C -0.09286(8) 0.64721(19) 0.03506(14) 0.0289(5) Uani 1 1 d . . . . .
C4 C -0.09553(8) 0.76761(19) -0.01290(14) 0.0281(5) Uani 1 1 d . . . . .
C5 C -0.14720(9) 0.8170(2) -0.06181(16) 0.0350(5) Uani 1 1 d . . . . .
C6 C -0.19609(9) 0.7450(2) -0.06632(17) 0.0398(6) Uani 1 1 d . . . . .
C7 C -0.19399(10) 0.6233(2) -0.02194(17) 0.0433(6) Uani 1 1 d . . . . .
C8 C -0.14328(9) 0.5763(2) 0.02838(16) 0.0370(5) Uani 1 1 d . . . . .
C9 C 0.06440(8) 0.58873(19) 0.15566(14) 0.0282(5) Uani 1 1 d . . . . .
C10 C 0.06573(9) 0.45569(19) 0.17976(15) 0.0310(5) Uani 1 1 d . . . . .
C11 C 0.11528(9) 0.3958(2) 0.22699(15) 0.0325(5) Uani 1 1 d . . . . .
C12 C 0.16507(9) 0.4691(2) 0.24991(15) 0.0326(5) Uani 1 1 d . . . . .
C13 C 0.16441(10) 0.6013(2) 0.22684(16) 0.0380(5) Uani 1 1 d . . . . .
C14 C 0.11468(9) 0.6600(2) 0.18130(16) 0.0357(5) Uani 1 1 d . . . . .
C15 C 0.21803(10) 0.4090(2) 0.29541(17) 0.0398(5) Uani 1 1 d . . . . .
C16 C 0.08644(8) 0.82328(19) -0.08014(14) 0.0295(5) Uani 1 1 d . . . . .
C17 C 0.14374(9) 0.8064(2) -0.04858(17) 0.0388(5) Uani 1 1 d . . . . .
C18 C 0.17978(11) 0.8779(3) -0.0906(2) 0.0523(7) Uani 1 1 d . . . . .
C19 C 0.15891(13) 0.9651(3) -0.1613(2) 0.0615(8) Uani 1 1 d . . . . .
C20 C 0.10144(13) 0.9826(3) -0.19125(19) 0.0599(8) Uani 1 1 d . . . . .
C21 C 0.06452(11) 0.9111(3) -0.15037(17) 0.0449(6) Uani 1 1 d . . . . .
H1N H -0.0510(9) 0.913(3) -0.0363(17) 0.047(7) Uiso 1 1 d . . . . .
H2 H -0.0433(9) 0.520(2) 0.1253(16) 0.043(6) Uiso 1 1 d . . . . .
H5 H -0.1490(8) 0.903(2) -0.0950(15) 0.036(6) Uiso 1 1 d . . . . .
H6 H -0.2319(9) 0.776(2) -0.0980(16) 0.044(6) Uiso 1 1 d . . . . .
H7 H -0.2295(11) 0.574(3) -0.0240(18) 0.067(8) Uiso 1 1 d . . . . .
H8 H -0.1391(9) 0.489(2) 0.0609(15) 0.042(6) Uiso 1 1 d . . . . .
H10 H 0.0308(10) 0.403(2) 0.1619(17) 0.053(7) Uiso 1 1 d . . . . .
H11 H 0.1153(8) 0.301(2) 0.2432(15) 0.040(6) Uiso 1 1 d . . . . .
H13 H 0.1990(9) 0.653(2) 0.2442(16) 0.044(6) Uiso 1 1 d . . . . .
H14 H 0.1150(9) 0.751(2) 0.1645(16) 0.048(6) Uiso 1 1 d . . . . .
H17 H 0.1575(9) 0.744(2) 0.0027(16) 0.041(6) Uiso 1 1 d . . . . .
H18 H 0.2201(12) 0.865(3) -0.072(2) 0.073(9) Uiso 1 1 d . . . . .
H19 H 0.1824(12) 1.013(3) -0.191(2) 0.077(9) Uiso 1 1 d . . . . .
H20 H 0.0857(11) 1.045(3) -0.239(2) 0.070(9) Uiso 1 1 d . . . . .
H21 H 0.0282(10) 0.924(2) -0.1691(18) 0.057(8) 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
P1 O1 1.4849(14) . ?
P1 O2 1.6132(14) . ?
P1 N1 1.6403(18) . ?
P1 C1 1.778(2) . ?
O2 C16 1.413(2) . ?
N1 C4 1.393(2) . ?
N1 H1N 0.85(3) . ?
N2 C15 1.148(3) . ?
C1 C2 1.362(3) . ?
C1 C9 1.494(3) . ?
C2 C3 1.446(3) . ?
C2 H2 0.96(2) . ?
C3 C8 1.411(3) . ?
C3 C4 1.411(3) . ?
C4 C5 1.396(3) . ?
C5 C6 1.389(3) . ?
C5 H5 1.00(2) . ?
C6 C7 1.399(3) . ?
C6 H6 0.95(2) . ?
C7 C8 1.376(3) . ?
C7 H7 1.00(3) . ?
C8 H8 1.01(2) . ?
C9 C14 1.403(3) . ?
C9 C10 1.405(3) . ?
C10 C11 1.392(3) . ?
C10 H10 0.99(2) . ?
C11 C12 1.402(3) . ?
C11 H11 1.00(2) . ?
C12 C13 1.394(3) . ?
C12 C15 1.450(3) . ?
C13 C14 1.383(3) . ?
C13 H13 0.98(2) . ?
C14 H14 0.97(2) . ?
C16 C21 1.377(3) . ?
C16 C17 1.380(3) . ?
C17 C18 1.384(3) . ?
C17 H17 0.98(2) . ?
C18 C19 1.372(4) . ?
C18 H18 0.97(3) . ?
C19 C20 1.382(4) . ?
C19 H19 0.93(3) . ?
C20 C21 1.389(3) . ?
C20 H20 0.96(3) . ?
C21 H21 0.87(2) . ?

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 109.73(8) . . ?
O1 P1 N1 111.90(9) . . ?
O2 P1 N1 108.88(9) . . ?
O1 P1 C1 120.04(9) . . ?
O2 P1 C1 101.18(8) . . ?
N1 P1 C1 104.22(9) . . ?
C16 O2 P1 121.86(12) . . ?
C4 N1 P1 128.45(16) . . ?
C4 N1 H1N 115.2(15) . . ?
P1 N1 H1N 116.3(15) . . ?
C2 C1 C9 123.46(18) . . ?
C2 C1 P1 118.29(15) . . ?
C9 C1 P1 118.02(14) . . ?
C1 C2 C3 127.5(2) . . ?
C1 C2 H2 117.1(13) . . ?
C3 C2 H2 115.3(13) . . ?
C8 C3 C4 118.10(19) . . ?
C8 C3 C2 120.44(19) . . ?
C4 C3 C2 121.45(18) . . ?
N1 C4 C5 119.81(19) . . ?
N1 C4 C3 119.72(18) . . ?
C5 C4 C3 120.46(18) . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 H5 119.8(12) . . ?
C4 C5 H5 120.3(12) . . ?
C5 C6 C7 120.5(2) . . ?
C5 C6 H6 122.1(14) . . ?
C7 C6 H6 117.4(14) . . ?
C8 C7 C6 119.6(2) . . ?
C8 C7 H7 120.6(15) . . ?
C6 C7 H7 119.7(15) . . ?
C7 C8 C3 121.4(2) . . ?
C7 C8 H8 123.2(12) . . ?
C3 C8 H8 115.3(12) . . ?
C14 C9 C10 117.85(18) . . ?
C14 C9 C1 120.73(18) . . ?
C10 C9 C1 121.37(18) . . ?
C11 C10 C9 121.4(2) . . ?
C11 C10 H10 119.4(14) . . ?
C9 C10 H10 119.3(14) . . ?
C10 C11 C12 119.4(2) . . ?
C10 C11 H11 120.0(12) . . ?
C12 C11 H11 120.6(12) . . ?
C13 C12 C11 119.96(19) . . ?
C13 C12 C15 119.0(2) . . ?
C11 C12 C15 121.07(19) . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 H13 120.1(13) . . ?
C12 C13 H13 119.9(13) . . ?
C13 C14 C9 121.4(2) . . ?
C13 C14 H14 119.2(13) . . ?
C9 C14 H14 119.3(13) . . ?
N2 C15 C12 178.0(3) . . ?
C21 C16 C17 121.8(2) . . ?
C21 C16 O2 119.32(18) . . ?
C17 C16 O2 118.83(18) . . ?
C16 C17 C18 118.6(2) . . ?
C16 C17 H17 118.9(13) . . ?
C18 C17 H17 122.4(13) . . ?
C19 C18 C17 120.6(2) . . ?
C19 C18 H18 119.2(17) . . ?
C17 C18 H18 120.1(17) . . ?
C18 C19 C20 120.2(2) . . ?
C18 C19 H19 121.9(18) . . ?
C20 C19 H19 117.9(18) . . ?
C19 C20 C21 120.1(3) . . ?
C19 C20 H20 121.9(16) . . ?
C21 C20 H20 118.0(17) . . ?
C16 C21 C20 118.7(2) . . ?
C16 C21 H21 121.7(17) . . ?
C20 C21 H21 119.6(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 P1 O2 C16 -22.03(16) . . . . ?
N1 P1 O2 C16 100.76(15) . . . . ?
C1 P1 O2 C16 -149.84(14) . . . . ?
O1 P1 N1 C4 -137.61(18) . . . . ?
O2 P1 N1 C4 100.92(19) . . . . ?
C1 P1 N1 C4 -6.4(2) . . . . ?
O1 P1 C1 C2 132.15(16) . . . . ?
O2 P1 C1 C2 -107.06(17) . . . . ?
N1 P1 C1 C2 5.92(19) . . . . ?
O1 P1 C1 C9 -53.15(18) . . . . ?
O2 P1 C1 C9 67.64(15) . . . . ?
N1 P1 C1 C9 -179.38(14) . . . . ?
C9 C1 C2 C3 -176.72(18) . . . . ?
P1 C1 C2 C3 -2.3(3) . . . . ?
C1 C2 C3 C8 177.7(2) . . . . ?
C1 C2 C3 C4 -2.7(3) . . . . ?
P1 N1 C4 C5 -177.82(16) . . . . ?
P1 N1 C4 C3 2.6(3) . . . . ?
C8 C3 C4 N1 -177.57(19) . . . . ?
C2 C3 C4 N1 2.8(3) . . . . ?
C8 C3 C4 C5 2.9(3) . . . . ?
C2 C3 C4 C5 -176.79(19) . . . . ?
N1 C4 C5 C6 178.0(2) . . . . ?
C3 C4 C5 C6 -2.4(3) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C5 C6 C7 C8 1.6(4) . . . . ?
C6 C7 C8 C3 -1.1(3) . . . . ?
C4 C3 C8 C7 -1.1(3) . . . . ?
C2 C3 C8 C7 178.6(2) . . . . ?
C2 C1 C9 C14 -166.4(2) . . . . ?
P1 C1 C9 C14 19.2(3) . . . . ?
C2 C1 C9 C10 16.2(3) . . . . ?
P1 C1 C9 C10 -158.16(16) . . . . ?
C14 C9 C10 C11 -0.4(3) . . . . ?
C1 C9 C10 C11 177.05(19) . . . . ?
C9 C10 C11 C12 -0.9(3) . . . . ?
C10 C11 C12 C13 1.1(3) . . . . ?
C10 C11 C12 C15 -177.3(2) . . . . ?
C11 C12 C13 C14 -0.1(3) . . . . ?
C15 C12 C13 C14 178.4(2) . . . . ?
C12 C13 C14 C9 -1.3(3) . . . . ?
C10 C9 C14 C13 1.5(3) . . . . ?
C1 C9 C14 C13 -176.0(2) . . . . ?
P1 O2 C16 C21 -81.5(2) . . . . ?
P1 O2 C16 C17 101.0(2) . . . . ?
C21 C16 C17 C18 -1.5(3) . . . . ?
O2 C16 C17 C18 175.88(19) . . . . ?
C16 C17 C18 C19 0.9(4) . . . . ?
C17 C18 C19 C20 0.1(4) . . . . ?
C18 C19 C20 C21 -0.5(4) . . . . ?
C17 C16 C21 C20 1.1(4) . . . . ?
O2 C16 C21 C20 -176.3(2) . . . . ?
C19 C20 C21 C16 -0.1(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.85(3) 1.96(3) 2.809(2) 172(2) 5_575

_refine_diff_density_max         0.246
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_cu_mh256_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1894571'
_audit_update_record             
;
2019-01-30 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H15 N2 O2 P'
_chemical_formula_weight         358.32

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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                   26.4131(8)
_cell_length_b                   9.7872(3)
_cell_length_c                   14.9148(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.7000(10)
_cell_angle_gamma                90
_cell_volume                     3474.22(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6119
_cell_measurement_theta_min      3.71
_cell_measurement_theta_max      66.48

_exptl_crystal_description       cut-block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    1.550
_shelx_estimated_absorpt_T_min   0.836
_shelx_estimated_absorpt_T_max   0.899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6814
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS'
_diffrn_measurement_device_type  'Bruker apex II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13564
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.714
_diffrn_reflns_theta_max         66.626
_diffrn_reflns_theta_full        66.626
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3071
_reflns_number_gt                2776
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0547P)²+2.4322P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3071
_refine_ls_number_parameters     295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0967
_refine_ls_wR_factor_gt          0.0930
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
P1 P 0.47615(2) 0.79192(4) 0.51064(3) 0.01900(14) Uani 1 1 d . . . . .
O1 O 0.44381(4) 0.90928(11) 0.52114(8) 0.0236(3) Uani 1 1 d . . . . .
O2 O 0.44875(4) 0.73663(11) 0.39843(8) 0.0246(3) Uani 1 1 d . . . . .
N1 N 0.54181(5) 0.83130(14) 0.53814(10) 0.0228(3) Uani 1 1 d . . . . .
N2 N 0.77801(6) 0.5783(2) 0.90478(12) 0.0441(4) Uani 1 1 d . . . . .
C1 C 0.48114(6) 0.64352(15) 0.58213(11) 0.0209(3) Uani 1 1 d . . . . .
C2 C 0.53254(6) 0.60205(16) 0.64900(12) 0.0238(3) Uani 1 1 d . . . . .
C3 C 0.58602(6) 0.66339(16) 0.66753(11) 0.0229(3) Uani 1 1 d . . . . .
C4 C 0.58980(6) 0.77646(15) 0.61291(11) 0.0209(3) Uani 1 1 d . . . . .
C5 C 0.64172(6) 0.83646(16) 0.63331(12) 0.0247(3) Uani 1 1 d . . . . .
C6 C 0.68983(7) 0.78458(17) 0.70808(12) 0.0269(4) Uani 1 1 d . . . . .
C7 C 0.68701(7) 0.67109(18) 0.76284(12) 0.0273(4) Uani 1 1 d . . . . .
C8 C 0.63553(7) 0.61077(17) 0.74229(12) 0.0268(3) Uani 1 1 d . . . . .
C9 C 0.73756(7) 0.61825(19) 0.84199(13) 0.0319(4) Uani 1 1 d . . . . .
C10 C 0.42818(6) 0.57011(17) 0.56447(11) 0.0235(3) Uani 1 1 d . . . . .
C11 C 0.42978(7) 0.43244(17) 0.58932(12) 0.0261(3) Uani 1 1 d . . . . .
C12 C 0.38072(7) 0.36218(18) 0.57132(13) 0.0305(4) Uani 1 1 d . . . . .
C13 C 0.32924(7) 0.4279(2) 0.52694(13) 0.0334(4) Uani 1 1 d . . . . .
C14 C 0.32695(7) 0.5638(2) 0.50157(13) 0.0338(4) Uani 1 1 d . . . . .
C15 C 0.37604(7) 0.63614(18) 0.52082(12) 0.0281(4) Uani 1 1 d . . . . .
C16 C 0.41391(6) 0.81869(16) 0.31763(11) 0.0227(3) Uani 1 1 d . . . . .
C17 C 0.35683(7) 0.7949(2) 0.27531(13) 0.0313(4) Uani 1 1 d . . . . .
C18 C 0.32259(8) 0.8705(2) 0.19258(13) 0.0407(5) Uani 1 1 d . . . . .
C19 C 0.34510(9) 0.9672(2) 0.15348(13) 0.0426(5) Uani 1 1 d . . . . .
C20 C 0.40225(9) 0.9902(2) 0.19701(14) 0.0408(5) Uani 1 1 d . . . . .
C21 C 0.43741(8) 0.91545(18) 0.28014(13) 0.0315(4) Uani 1 1 d . . . . .
H1N H 0.5445(8) 0.909(2) 0.5151(16) 0.035(5) Uiso 1 1 d . . . . .
H2 H 0.5352(7) 0.520(2) 0.6909(14) 0.030(5) Uiso 1 1 d . . . . .
H5 H 0.6426(7) 0.915(2) 0.5948(14) 0.027(5) Uiso 1 1 d . . . . .
H6 H 0.7259(9) 0.826(2) 0.7238(15) 0.038(5) Uiso 1 1 d . . . . .
H8 H 0.6333(8) 0.530(2) 0.7824(14) 0.034(5) Uiso 1 1 d . . . . .
H11 H 0.4664(9) 0.383(2) 0.6178(16) 0.039(5) Uiso 1 1 d . . . . .
H12 H 0.3835(9) 0.266(2) 0.5912(16) 0.040(5) Uiso 1 1 d . . . . .
H13 H 0.2962(9) 0.376(2) 0.5152(16) 0.040(5) Uiso 1 1 d . . . . .
H14 H 0.2906(9) 0.614(2) 0.4729(16) 0.045(6) Uiso 1 1 d . . . . .
H15 H 0.3746(8) 0.730(2) 0.5071(15) 0.034(5) Uiso 1 1 d . . . . .
H17 H 0.3433(9) 0.727(2) 0.3041(16) 0.039(6) Uiso 1 1 d . . . . .
H18 H 0.2809(10) 0.855(2) 0.1620(17) 0.049(6) Uiso 1 1 d . . . . .
H19 H 0.3212(10) 1.020(2) 0.0952(18) 0.054(6) Uiso 1 1 d . . . . .
H20 H 0.4184(10) 1.055(3) 0.1723(18) 0.052(6) Uiso 1 1 d . . . . .
H21 H 0.4775(9) 0.925(2) 0.3126(16) 0.040(5) 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
P1 O1 1.4796(11) . ?
P1 O2 1.6022(11) . ?
P1 N1 1.6455(13) . ?
P1 C1 1.7726(15) . ?
O2 C16 1.4080(19) . ?
N1 C4 1.383(2) . ?
N1 H1N 0.85(2) . ?
N2 C9 1.142(2) . ?
C1 C2 1.352(2) . ?
C1 C10 1.491(2) . ?
C2 C3 1.447(2) . ?
C2 H2 1.00(2) . ?
C3 C8 1.398(2) . ?
C3 C4 1.403(2) . ?
C4 C5 1.399(2) . ?
C5 C6 1.374(2) . ?
C5 H5 0.96(2) . ?
C6 C7 1.400(2) . ?
C6 H6 0.97(2) . ?
C7 C8 1.389(2) . ?
C7 C9 1.441(2) . ?
C8 H8 1.01(2) . ?
C10 C11 1.393(2) . ?
C10 C15 1.400(2) . ?
C11 C12 1.386(2) . ?
C11 H11 0.99(2) . ?
C12 C13 1.386(3) . ?
C12 H12 0.98(2) . ?
C13 C14 1.377(3) . ?
C13 H13 0.96(2) . ?
C14 C15 1.394(2) . ?
C14 H14 0.99(2) . ?
C15 H15 0.94(2) . ?
C16 C21 1.377(2) . ?
C16 C17 1.378(2) . ?
C17 C18 1.386(3) . ?
C17 H17 0.94(2) . ?
C18 C19 1.375(3) . ?
C18 H18 1.00(2) . ?
C19 C20 1.379(3) . ?
C19 H19 0.97(3) . ?
C20 C21 1.391(3) . ?
C20 H20 0.93(3) . ?
C21 H21 0.96(2) . ?

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 110.66(6) . . ?
O1 P1 N1 112.72(7) . . ?
O2 P1 N1 106.81(6) . . ?
O1 P1 C1 117.91(7) . . ?
O2 P1 C1 103.51(7) . . ?
N1 P1 C1 104.27(7) . . ?
C16 O2 P1 122.20(10) . . ?
C4 N1 P1 127.48(11) . . ?
C4 N1 H1N 117.8(14) . . ?
P1 N1 H1N 111.8(13) . . ?
C2 C1 C10 123.41(14) . . ?
C2 C1 P1 118.60(12) . . ?
C10 C1 P1 117.99(11) . . ?
C1 C2 C3 126.95(15) . . ?
C1 C2 H2 118.5(10) . . ?
C3 C2 H2 114.6(10) . . ?
C8 C3 C4 118.45(14) . . ?
C8 C3 C2 119.84(14) . . ?
C4 C3 C2 121.71(14) . . ?
N1 C4 C5 118.80(14) . . ?
N1 C4 C3 120.22(14) . . ?
C5 C4 C3 120.98(14) . . ?
C6 C5 C4 119.73(15) . . ?
C6 C5 H5 121.7(11) . . ?
C4 C5 H5 118.6(11) . . ?
C5 C6 C7 120.17(15) . . ?
C5 C6 H6 120.6(13) . . ?
C7 C6 H6 119.2(13) . . ?
C8 C7 C6 120.21(15) . . ?
C8 C7 C9 119.92(16) . . ?
C6 C7 C9 119.86(15) . . ?
C7 C8 C3 120.46(15) . . ?
C7 C8 H8 120.4(11) . . ?
C3 C8 H8 119.1(11) . . ?
N2 C9 C7 178.9(2) . . ?
C11 C10 C15 118.70(15) . . ?
C11 C10 C1 120.09(14) . . ?
C15 C10 C1 121.20(15) . . ?
C12 C11 C10 120.69(16) . . ?
C12 C11 H11 119.8(12) . . ?
C10 C11 H11 119.5(12) . . ?
C13 C12 C11 120.22(17) . . ?
C13 C12 H12 121.3(12) . . ?
C11 C12 H12 118.5(12) . . ?
C14 C13 C12 119.78(15) . . ?
C14 C13 H13 122.2(13) . . ?
C12 C13 H13 118.0(13) . . ?
C13 C14 C15 120.53(17) . . ?
C13 C14 H14 120.8(13) . . ?
C15 C14 H14 118.6(13) . . ?
C14 C15 C10 120.07(17) . . ?
C14 C15 H15 120.4(12) . . ?
C10 C15 H15 119.5(12) . . ?
C21 C16 C17 121.76(15) . . ?
C21 C16 O2 119.83(14) . . ?
C17 C16 O2 118.34(15) . . ?
C16 C17 C18 118.65(18) . . ?
C16 C17 H17 117.8(13) . . ?
C18 C17 H17 123.5(13) . . ?
C19 C18 C17 120.67(18) . . ?
C19 C18 H18 120.3(13) . . ?
C17 C18 H18 119.0(13) . . ?
C18 C19 C20 119.93(17) . . ?
C18 C19 H19 120.9(14) . . ?
C20 C19 H19 119.2(14) . . ?
C19 C20 C21 120.36(18) . . ?
C19 C20 H20 121.6(15) . . ?
C21 C20 H20 118.1(15) . . ?
C16 C21 C20 118.63(17) . . ?
C16 C21 H21 116.9(13) . . ?
C20 C21 H21 124.4(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 P1 O2 C16 22.16(13) . . . . ?
N1 P1 O2 C16 -100.87(12) . . . . ?
C1 P1 O2 C16 149.41(11) . . . . ?
O1 P1 N1 C4 118.58(13) . . . . ?
O2 P1 N1 C4 -119.67(13) . . . . ?
C1 P1 N1 C4 -10.48(15) . . . . ?
O1 P1 C1 C2 -118.64(13) . . . . ?
O2 P1 C1 C2 118.81(13) . . . . ?
N1 P1 C1 C2 7.21(14) . . . . ?
O1 P1 C1 C10 61.92(13) . . . . ?
O2 P1 C1 C10 -60.63(12) . . . . ?
N1 P1 C1 C10 -172.22(11) . . . . ?
C10 C1 C2 C3 176.97(14) . . . . ?
P1 C1 C2 C3 -2.4(2) . . . . ?
C1 C2 C3 C8 177.65(16) . . . . ?
C1 C2 C3 C4 -1.6(3) . . . . ?
P1 N1 C4 C5 -171.32(12) . . . . ?
P1 N1 C4 C3 8.1(2) . . . . ?
C8 C3 C4 N1 179.82(14) . . . . ?
C2 C3 C4 N1 -0.9(2) . . . . ?
C8 C3 C4 C5 -0.7(2) . . . . ?
C2 C3 C4 C5 178.53(14) . . . . ?
N1 C4 C5 C6 179.22(14) . . . . ?
C3 C4 C5 C6 -0.2(2) . . . . ?
C4 C5 C6 C7 0.8(2) . . . . ?
C5 C6 C7 C8 -0.4(2) . . . . ?
C5 C6 C7 C9 -179.24(15) . . . . ?
C6 C7 C8 C3 -0.6(2) . . . . ?
C9 C7 C8 C3 178.24(15) . . . . ?
C4 C3 C8 C7 1.2(2) . . . . ?
C2 C3 C8 C7 -178.12(14) . . . . ?
C2 C1 C10 C11 -22.5(2) . . . . ?
P1 C1 C10 C11 156.93(12) . . . . ?
C2 C1 C10 C15 159.05(16) . . . . ?
P1 C1 C10 C15 -21.55(19) . . . . ?
C15 C10 C11 C12 -0.1(2) . . . . ?
C1 C10 C11 C12 -178.61(14) . . . . ?
C10 C11 C12 C13 0.9(2) . . . . ?
C11 C12 C13 C14 -0.6(3) . . . . ?
C12 C13 C14 C15 -0.5(3) . . . . ?
C13 C14 C15 C10 1.3(3) . . . . ?
C11 C10 C15 C14 -1.0(2) . . . . ?
C1 C10 C15 C14 177.50(15) . . . . ?
P1 O2 C16 C21 78.04(17) . . . . ?
P1 O2 C16 C17 -104.87(15) . . . . ?
C21 C16 C17 C18 0.3(3) . . . . ?
O2 C16 C17 C18 -176.72(15) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C17 C18 C19 C20 -0.3(3) . . . . ?
C18 C19 C20 C21 0.3(3) . . . . ?
C17 C16 C21 C20 -0.3(3) . . . . ?
O2 C16 C21 C20 176.68(15) . . . . ?
C19 C20 C21 C16 0.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.85(2) 1.92(2) 2.7683(17) 173(2) 5_676
C5 H5 N2 0.96(2) 2.637(19) 3.386(2) 134.9(14) 4_656

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.053



