# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
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# Crystallographic Data Centre (CCDC).
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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data_mo_20180102-yql-1_0m
_database_code_depnum_ccdc_archive 'CCDC 1873308'
_audit_update_record             
;
2018-10-15 deposited with the CCDC.
2018-12-17 downloaded from the CCDC.
;
_audit_creation_date             2018-01-30
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.01.22 svn.r3481 for OlexSys, GUI svn.r5457)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H23 N2 O3 P'
_chemical_formula_sum            'C20 H23 N2 O3 P'
_chemical_formula_weight         370.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.115(3)
_cell_length_b                   9.448(2)
_cell_length_c                   11.944(3)
_cell_angle_alpha                101.46(2)
_cell_angle_beta                 91.031(6)
_cell_angle_gamma                106.620(7)
_cell_volume                     962.9(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2528
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.418
_cell_measurement_theta_min      2.576
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1116 before and 0.0573 after correction. The Ratio of minimum to maximum transmission is 0.8150. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.897
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7228
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         1.745
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.897
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2815
_reflns_number_total             3525
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.170
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3525
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0841
_refine_ls_restrained_S_all      1.170
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1082P)²+4.0677P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2742
_refine_ls_wR_factor_ref         0.2831
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9961(7)
 0.0039(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B)
3.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C8(H8), C12(H12), C16(H16), C5(H5), C7(H7), C6(H6), C15(H15),
 C13(H13), C14(H14)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.55633(14) 0.78041(16) 0.30721(11) 0.0250(4) Uani 1 1 d . . . . .
O3 O 0.5783(4) 0.9111(4) 0.2401(4) 0.0352(10) Uani 1 1 d . . . . .
O2 O 0.5473(4) 0.6401(4) 0.2061(3) 0.0342(9) Uani 1 1 d . . . . .
N2 N -0.0528(4) 0.7484(5) 0.4836(3) 0.0258(10) Uani 1 1 d . . . . .
H2 H -0.1305 0.7424 0.4363 0.031 Uiso 1 1 calc R . . . .
O1 O 0.6805(4) 0.8027(5) 0.3953(3) 0.0362(10) Uani 1 1 d . . . . .
N1 N 0.2010(5) 0.7556(5) 0.5096(3) 0.0253(9) Uani 1 1 d . . . . .
C4 C 0.2391(5) 0.7361(5) 0.2743(4) 0.0206(10) Uani 1 1 d . . . . .
C10 C 0.0833(5) 0.7446(5) 0.4391(4) 0.0215(10) Uani 1 1 d . . . . .
C2 C 0.3400(5) 0.7614(6) 0.4695(4) 0.0256(11) Uani 1 1 d . . . . .
C11 C -0.0760(5) 0.7617(6) 0.6025(4) 0.0228(10) Uani 1 1 d . . . . .
C8 C -0.0382(6) 0.6953(6) 0.2393(4) 0.0272(11) Uani 1 1 d . . . . .
H8 H -0.1359 0.6878 0.2683 0.033 Uiso 1 1 calc R . . . .
C12 C -0.0421(6) 0.6626(6) 0.6640(4) 0.0284(11) Uani 1 1 d . . . . .
H12 H 0.0006 0.5862 0.6278 0.034 Uiso 1 1 calc R . . . .
C16 C -0.1404(6) 0.8722(6) 0.6556(5) 0.0289(11) Uani 1 1 d . . . . .
H16 H -0.1656 0.9381 0.6131 0.035 Uiso 1 1 calc R . . . .
C5 C 0.2476(6) 0.7187(6) 0.1539(4) 0.0265(11) Uani 1 1 d . . . . .
H5 H 0.3443 0.7270 0.1231 0.032 Uiso 1 1 calc R . . . .
C7 C -0.0253(6) 0.6764(6) 0.1239(5) 0.0293(11) Uani 1 1 d . . . . .
H7 H -0.1137 0.6541 0.0726 0.035 Uiso 1 1 calc R . . . .
C6 C 0.1205(6) 0.6904(6) 0.0817(4) 0.0288(11) Uani 1 1 d . . . . .
H6 H 0.1302 0.6799 0.0016 0.035 Uiso 1 1 calc R . . . .
C15 C -0.1675(7) 0.8860(7) 0.7703(5) 0.0353(13) Uani 1 1 d . . . . .
H15 H -0.2106 0.9620 0.8067 0.042 Uiso 1 1 calc R . . . .
C9 C 0.0925(5) 0.7260(5) 0.3160(4) 0.0204(10) Uani 1 1 d . . . . .
C13 C -0.0712(6) 0.6765(6) 0.7787(5) 0.0343(13) Uani 1 1 d . . . . .
H13 H -0.0495 0.6085 0.8208 0.041 Uiso 1 1 calc R . . . .
C3 C 0.3687(5) 0.7585(6) 0.3556(4) 0.0236(10) Uani 1 1 d . . . . .
C14 C -0.1319(7) 0.7889(7) 0.8323(5) 0.0377(13) Uani 1 1 d . . . . .
H14 H -0.1491 0.7994 0.9113 0.045 Uiso 1 1 calc R . . . .
C1 C 0.4589(7) 0.7731(9) 0.5642(5) 0.0444(16) Uani 1 1 d . . . . .
H1A H 0.4074 0.7517 0.6329 0.067 Uiso 1 1 calc GR . . . .
H1B H 0.5308 0.8754 0.5818 0.067 Uiso 1 1 calc GR . . . .
H1C H 0.5152 0.6997 0.5390 0.067 Uiso 1 1 calc GR . . . .
C17 C 0.7270(7) 0.9765(9) 0.2000(6) 0.0486(17) Uani 1 1 d . . . . .
H17A H 0.7848 1.0687 0.2563 0.058 Uiso 1 1 calc R . . . .
H17B H 0.7872 0.9034 0.1918 0.058 Uiso 1 1 calc R . . . .
C19 C 0.5201(8) 0.4923(7) 0.2341(6) 0.0498(17) Uani 1 1 d . . . . .
H19A H 0.4146 0.4576 0.2580 0.060 Uiso 1 1 calc R . . . .
H19B H 0.5936 0.4980 0.2980 0.060 Uiso 1 1 calc R . . . .
C18 C 0.7051(9) 1.0144(11) 0.0905(7) 0.068(2) Uani 1 1 d . . . . .
H18A H 0.6581 0.9216 0.0329 0.102 Uiso 1 1 calc GR . . . .
H18B H 0.8047 1.0678 0.0670 0.102 Uiso 1 1 calc GR . . . .
H18C H 0.6377 1.0795 0.0973 0.102 Uiso 1 1 calc GR . . . .
C20 C 0.5403(10) 0.3851(9) 0.1305(8) 0.074(3) Uani 1 1 d . . . . .
H20A H 0.5173 0.2835 0.1464 0.111 Uiso 1 1 calc GR . . . .
H20B H 0.6466 0.4173 0.1100 0.111 Uiso 1 1 calc GR . . . .
H20C H 0.4704 0.3837 0.0667 0.111 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O3 1.571(4) . ?
P1 O2 1.587(4) . ?
P1 O1 1.471(4) . ?
P1 C3 1.784(5) . ?
O3 C17 1.452(7) . ?
O2 C19 1.454(7) . ?
N2 H2 0.8800 . ?
N2 C10 1.365(6) . ?
N2 C11 1.426(6) . ?
N1 C10 1.320(6) . ?
N1 C2 1.353(6) . ?
C4 C5 1.421(7) . ?
C4 C9 1.418(6) . ?
C4 C3 1.455(6) . ?
C10 C9 1.452(7) . ?
C2 C3 1.386(7) . ?
C2 C1 1.518(7) . ?
C11 C12 1.394(7) . ?
C11 C16 1.392(7) . ?
C8 H8 0.9500 . ?
C8 C7 1.365(7) . ?
C8 C9 1.415(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(8) . ?
C16 H16 0.9500 . ?
C16 C15 1.384(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.362(7) . ?
C7 H7 0.9500 . ?
C7 C6 1.410(7) . ?
C6 H6 0.9500 . ?
C15 H15 0.9500 . ?
C15 C14 1.388(8) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(9) . ?
C14 H14 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.448(10) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.486(10) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
O3 P1 O2 101.4(2) . . ?
O3 P1 C3 103.4(2) . . ?
O2 P1 C3 107.9(2) . . ?
O1 P1 O3 115.1(2) . . ?
O1 P1 O2 111.5(2) . . ?
O1 P1 C3 116.3(2) . . ?
C17 O3 P1 120.1(4) . . ?
C19 O2 P1 118.2(4) . . ?
C10 N2 H2 118.2 . . ?
C10 N2 C11 123.7(4) . . ?
C11 N2 H2 118.2 . . ?
C10 N1 C2 120.2(4) . . ?
C5 C4 C3 124.4(4) . . ?
C9 C4 C5 116.9(4) . . ?
C9 C4 C3 118.7(4) . . ?
N2 C10 C9 119.0(4) . . ?
N1 C10 N2 118.6(4) . . ?
N1 C10 C9 122.4(4) . . ?
N1 C2 C3 123.4(4) . . ?
N1 C2 C1 111.8(4) . . ?
C3 C2 C1 124.8(4) . . ?
C12 C11 N2 121.3(4) . . ?
C16 C11 N2 118.5(4) . . ?
C16 C11 C12 120.1(5) . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.7(5) . . ?
C9 C8 H8 119.7 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.4(5) . . ?
C13 C12 H12 120.3 . . ?
C11 C16 H16 120.0 . . ?
C15 C16 C11 120.0(5) . . ?
C15 C16 H16 120.0 . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.6(5) . . ?
C6 C5 H5 119.2 . . ?
C8 C7 H7 120.3 . . ?
C8 C7 C6 119.3(5) . . ?
C6 C7 H7 120.3 . . ?
C5 C6 C7 121.0(5) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C16 C15 H15 120.0 . . ?
C16 C15 C14 120.1(5) . . ?
C14 C15 H15 120.0 . . ?
C4 C9 C10 117.1(4) . . ?
C8 C9 C4 120.5(4) . . ?
C8 C9 C10 122.3(4) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.5(5) . . ?
C14 C13 H13 119.8 . . ?
C4 C3 P1 120.0(4) . . ?
C2 C3 P1 122.3(4) . . ?
C2 C3 C4 117.7(4) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 119.9(5) . . ?
C13 C14 H14 120.0 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O3 C17 H17A 109.8 . . ?
O3 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
C18 C17 O3 109.4(5) . . ?
C18 C17 H17A 109.8 . . ?
C18 C17 H17B 109.8 . . ?
O2 C19 H19A 110.1 . . ?
O2 C19 H19B 110.1 . . ?
O2 C19 C20 108.2(6) . . ?
H19A C19 H19B 108.4 . . ?
C20 C19 H19A 110.1 . . ?
C20 C19 H19B 110.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 O3 C17 C18 144.0(6) . . . . ?
P1 O2 C19 C20 -171.4(5) . . . . ?
O3 P1 O2 C19 -177.5(4) . . . . ?
O3 P1 C3 C4 52.8(4) . . . . ?
O3 P1 C3 C2 -127.4(4) . . . . ?
O2 P1 O3 C17 -76.6(5) . . . . ?
O2 P1 C3 C4 -54.1(4) . . . . ?
O2 P1 C3 C2 125.7(4) . . . . ?
N2 C10 C9 C4 174.5(4) . . . . ?
N2 C10 C9 C8 -7.0(7) . . . . ?
N2 C11 C12 C13 -177.9(5) . . . . ?
N2 C11 C16 C15 178.6(5) . . . . ?
O1 P1 O3 C17 43.9(5) . . . . ?
O1 P1 O2 C19 59.6(5) . . . . ?
O1 P1 C3 C4 179.9(4) . . . . ?
O1 P1 C3 C2 -0.3(5) . . . . ?
N1 C10 C9 C4 -6.6(7) . . . . ?
N1 C10 C9 C8 171.9(5) . . . . ?
N1 C2 C3 P1 175.2(4) . . . . ?
N1 C2 C3 C4 -5.0(8) . . . . ?
C4 C5 C6 C7 -0.4(8) . . . . ?
C10 N2 C11 C12 -53.5(7) . . . . ?
C10 N2 C11 C16 129.3(5) . . . . ?
C10 N1 C2 C3 0.9(8) . . . . ?
C10 N1 C2 C1 -179.7(5) . . . . ?
C2 N1 C10 N2 -176.0(4) . . . . ?
C2 N1 C10 C9 5.1(7) . . . . ?
C11 N2 C10 N1 -0.9(7) . . . . ?
C11 N2 C10 C9 178.1(4) . . . . ?
C11 C12 C13 C14 -0.7(8) . . . . ?
C11 C16 C15 C14 -0.6(8) . . . . ?
C8 C7 C6 C5 1.6(8) . . . . ?
C12 C11 C16 C15 1.4(8) . . . . ?
C12 C13 C14 C15 1.6(9) . . . . ?
C16 C11 C12 C13 -0.8(8) . . . . ?
C16 C15 C14 C13 -1.0(9) . . . . ?
C5 C4 C9 C10 -179.6(4) . . . . ?
C5 C4 C9 C8 1.8(7) . . . . ?
C5 C4 C3 P1 4.9(7) . . . . ?
C5 C4 C3 C2 -174.8(5) . . . . ?
C7 C8 C9 C4 -0.6(7) . . . . ?
C7 C8 C9 C10 -179.1(5) . . . . ?
C9 C4 C5 C6 -1.4(7) . . . . ?
C9 C4 C3 P1 -177.1(3) . . . . ?
C9 C4 C3 C2 3.1(7) . . . . ?
C9 C8 C7 C6 -1.1(8) . . . . ?
C3 P1 O3 C17 171.7(5) . . . . ?
C3 P1 O2 C19 -69.2(4) . . . . ?
C3 C4 C5 C6 176.6(5) . . . . ?
C3 C4 C9 C10 2.3(6) . . . . ?
C3 C4 C9 C8 -176.2(4) . . . . ?
C1 C2 C3 P1 -4.0(8) . . . . ?
C1 C2 C3 C4 175.8(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9961(7)
2 0.0039(7)

####################################################################### 
# 
# 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_20180104-yql-2_0m
_database_code_depnum_ccdc_archive 'CCDC 1873345'
_audit_update_record             
;
2018-10-15 deposited with the CCDC.
2018-12-17 downloaded from the CCDC.
;
_audit_creation_date             2018-01-30
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.01.22 svn.r3481 for OlexSys, GUI svn.r5457)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 N O3 P'
_chemical_formula_sum            'C18 H20 N O3 P'
_chemical_formula_weight         329.32
_chemical_absolute_configuration syn
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   7.6453(19)
_cell_length_b                   11.642(3)
_cell_length_c                   9.808(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.969(8)
_cell_angle_gamma                90
_cell_volume                     850.7(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    737
_cell_measurement_temperature    173
_cell_measurement_theta_max      19.480
_cell_measurement_theta_min      2.736
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6329
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0762 before and 0.0600 after correction. The Ratio of minimum to maximum transmission is 0.8490. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0962
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6393
_diffrn_reflns_point_group_measured_fraction_full 0.930
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.312
_diffrn_reflns_theta_min         1.749
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.863
_reflns_Friedel_fraction_full    0.881
_reflns_Friedel_fraction_max     0.838
_reflns_number_gt                2380
_reflns_number_total             3451
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 
;
 Flack x determined using 779 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.16(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.883
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3451
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0586
_refine_ls_restrained_S_all      0.882
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1677
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C10(H10), C6(H6), C3(H3), C12(H12), C4(H4), C14(H14),
 C11(H11), C13(H13)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.70639(18) 0.26288(13) 0.52738(16) 0.0346(4) Uani 1 1 d . . . . .
O3 O 0.8272(5) 0.1974(4) 0.4592(4) 0.0411(10) Uani 1 1 d . . . . .
O2 O 0.7433(6) 0.2464(4) 0.6911(4) 0.0371(10) Uani 1 1 d . . . . .
O1 O 0.7208(6) 0.3973(3) 0.5155(5) 0.0463(12) Uani 1 1 d . . . . .
N1 N 0.1833(6) 0.2043(4) 0.4360(5) 0.0325(11) Uani 1 1 d . . . . .
H1 H 0.0759 0.2052 0.4545 0.039 Uiso 1 1 calc R . . . .
C8 C 0.3348(8) 0.2481(5) 0.5210(6) 0.0296(12) Uani 1 1 d . . . . .
C7 C 0.2228(8) 0.1586(5) 0.3168(6) 0.0306(12) Uani 1 1 d . . . . .
C2 C 0.4066(8) 0.1734(5) 0.3255(6) 0.0311(13) Uani 1 1 d . . . . .
C5 C 0.1843(8) 0.0630(5) 0.1009(7) 0.0411(15) Uani 1 1 d . . . . .
H5 H 0.1105 0.0248 0.0232 0.049 Uiso 1 1 calc R . . . .
C9 C 0.3212(7) 0.2997(5) 0.6544(6) 0.0314(12) Uani 1 1 d . . . . .
C10 C 0.2215(8) 0.2443(5) 0.7377(6) 0.0366(14) Uani 1 1 d . . . . .
H10 H 0.1683 0.1718 0.7098 0.044 Uiso 1 1 calc R . . . .
C6 C 0.1096(9) 0.1050(5) 0.2063(6) 0.0373(13) Uani 1 1 d . . . . .
H6 H -0.0151 0.0972 0.2028 0.045 Uiso 1 1 calc R . . . .
C3 C 0.4796(8) 0.1309(5) 0.2172(6) 0.0377(14) Uani 1 1 d . . . . .
H3 H 0.6037 0.1397 0.2192 0.045 Uiso 1 1 calc R . . . .
C12 C 0.2751(10) 0.3984(7) 0.9021(8) 0.0551(19) Uani 1 1 d . . . . .
H12 H 0.2580 0.4327 0.9860 0.066 Uiso 1 1 calc R . . . .
C1 C 0.4796(7) 0.2321(5) 0.4581(6) 0.0317(12) Uani 1 1 d . . . . .
C15 C 0.7536(10) 0.1316(5) 0.7477(7) 0.0484(17) Uani 1 1 d . . . . .
H15A H 0.8752 0.0999 0.7537 0.058 Uiso 1 1 calc R . . . .
H15B H 0.6660 0.0815 0.6853 0.058 Uiso 1 1 calc R . . . .
C4 C 0.3670(9) 0.0759(6) 0.1073(7) 0.0450(16) Uani 1 1 d . . . . .
H4 H 0.4155 0.0459 0.0336 0.054 Uiso 1 1 calc R . . . .
C14 C 0.4004(8) 0.4046(6) 0.7005(7) 0.0422(15) Uani 1 1 d . . . . .
H14 H 0.4722 0.4425 0.6469 0.051 Uiso 1 1 calc R . . . .
C11 C 0.1998(10) 0.2939(7) 0.8599(7) 0.0495(17) Uani 1 1 d . . . . .
H11 H 0.1316 0.2553 0.9159 0.059 Uiso 1 1 calc R . . . .
C13 C 0.3769(10) 0.4537(6) 0.8210(8) 0.0542(18) Uani 1 1 d . . . . .
H13 H 0.4301 0.5260 0.8498 0.065 Uiso 1 1 calc R . . . .
C16 C 0.7141(11) 0.1344(7) 0.8884(7) 0.062(2) Uani 1 1 d . . . . .
H16A H 0.5927 0.1643 0.8816 0.092 Uiso 1 1 calc GR . . . .
H16B H 0.8011 0.1842 0.9497 0.092 Uiso 1 1 calc GR . . . .
H16C H 0.7224 0.0565 0.9272 0.092 Uiso 1 1 calc GR . . . .
C17 C 0.8861(10) 0.4586(7) 0.5700(11) 0.074(3) Uani 1 1 d . . . . .
H17A H 0.9514 0.4216 0.6576 0.088 Uiso 1 1 calc R . . . .
H17B H 0.9634 0.4552 0.5015 0.088 Uiso 1 1 calc R . . . .
C18 C 0.8500(17) 0.5744(9) 0.597(2) 0.145(6) Uani 1 1 d . . . . .
H18A H 0.8024 0.6140 0.5080 0.218 Uiso 1 1 calc GR . . . .
H18B H 0.9611 0.6120 0.6457 0.218 Uiso 1 1 calc GR . . . .
H18C H 0.7615 0.5776 0.6550 0.218 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O3 1.469(4) . ?
P1 O2 1.579(4) . ?
P1 O1 1.575(4) . ?
P1 C1 1.751(6) . ?
O2 C15 1.442(7) . ?
O1 C17 1.445(8) . ?
N1 H1 0.8800 . ?
N1 C8 1.366(7) . ?
N1 C7 1.378(7) . ?
C8 C9 1.465(8) . ?
C8 C1 1.396(8) . ?
C7 C2 1.400(8) . ?
C7 C6 1.375(8) . ?
C2 C3 1.397(8) . ?
C2 C1 1.463(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.378(9) . ?
C5 C4 1.392(10) . ?
C9 C10 1.394(8) . ?
C9 C14 1.392(8) . ?
C10 H10 0.9500 . ?
C10 C11 1.374(9) . ?
C6 H6 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.376(10) . ?
C12 H12 0.9500 . ?
C12 C11 1.369(11) . ?
C12 C13 1.389(11) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.478(10) . ?
C4 H4 0.9500 . ?
C14 H14 0.9500 . ?
C14 C13 1.361(10) . ?
C11 H11 0.9500 . ?
C13 H13 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.413(13) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

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
O3 P1 O2 114.4(2) . . ?
O3 P1 O1 114.9(3) . . ?
O3 P1 C1 112.7(3) . . ?
O2 P1 C1 107.8(3) . . ?
O1 P1 O2 101.3(2) . . ?
O1 P1 C1 104.7(3) . . ?
C15 O2 P1 119.1(4) . . ?
C17 O1 P1 122.2(5) . . ?
C8 N1 H1 124.9 . . ?
C8 N1 C7 110.2(5) . . ?
C7 N1 H1 124.9 . . ?
N1 C8 C9 118.6(5) . . ?
N1 C8 C1 109.1(5) . . ?
C1 C8 C9 132.3(5) . . ?
N1 C7 C2 107.9(5) . . ?
C6 C7 N1 128.6(6) . . ?
C6 C7 C2 123.4(6) . . ?
C7 C2 C1 106.8(5) . . ?
C3 C2 C7 118.4(5) . . ?
C3 C2 C1 134.7(5) . . ?
C6 C5 H5 119.8 . . ?
C6 C5 C4 120.5(6) . . ?
C4 C5 H5 119.8 . . ?
C10 C9 C8 119.4(5) . . ?
C14 C9 C8 122.4(5) . . ?
C14 C9 C10 118.1(5) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.3(6) . . ?
C11 C10 H10 119.8 . . ?
C7 C6 C5 117.3(6) . . ?
C7 C6 H6 121.4 . . ?
C5 C6 H6 121.4 . . ?
C2 C3 H3 120.9 . . ?
C4 C3 C2 118.3(6) . . ?
C4 C3 H3 120.9 . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.4(6) . . ?
C13 C12 H12 120.3 . . ?
C8 C1 P1 128.0(4) . . ?
C8 C1 C2 105.9(5) . . ?
C2 C1 P1 125.9(4) . . ?
O2 C15 H15A 109.8 . . ?
O2 C15 H15B 109.8 . . ?
O2 C15 C16 109.5(6) . . ?
H15A C15 H15B 108.2 . . ?
C16 C15 H15A 109.8 . . ?
C16 C15 H15B 109.8 . . ?
C5 C4 H4 119.0 . . ?
C3 C4 C5 122.1(6) . . ?
C3 C4 H4 119.0 . . ?
C9 C14 H14 119.4 . . ?
C13 C14 C9 121.2(6) . . ?
C13 C14 H14 119.4 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.8(7) . . ?
C12 C11 H11 119.6 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.2(7) . . ?
C14 C13 H13 119.9 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C17 H17A 109.6 . . ?
O1 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C18 C17 O1 110.4(8) . . ?
C18 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
