# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_6augb_0m
_database_code_depnum_ccdc_archive 'CCDC 1417598'
_audit_update_record             
;
2015-08-08 deposited with the CCDC.
2015-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'Dimethyl 5-chloro-2-(2-diazoacetyl)phenylphosphoramidate '
_chemical_name_common            ?
_chemical_melting_point          373-375
_chemical_formula_moiety         'C10 H11 Cl N3 O4 P'
_chemical_formula_sum            'C10 H11 Cl N3 O4 P'
_chemical_formula_weight         303.64

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.927(5)
_cell_length_b                   8.999(5)
_cell_length_c                   13.598(5)
_cell_angle_alpha                106.549(5)
_cell_angle_beta                 97.092(5)
_cell_angle_gamma                94.090(5)
_cell_volume                     685.6(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      25.50

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312
_exptl_absorpt_coefficient_mu    0.408
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6418
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABAS 2.10 (Bruker 2003)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8330
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_sigmaI/netI    0.0702
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.43
_diffrn_reflns_theta_max         25.50
_reflns_number_total             2555
_reflns_number_gt                1509
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART 5.628 (Bruker, 2003)'
_computing_cell_refinement       'SAINT 6.45 ( Bruker, 2003)'
_computing_data_reduction        'SAINT 6.45  (Bruker, 2003)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Diamond 2.1e'
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0666P)²+0.1861P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2555
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_ref         0.1463
_refine_ls_wR_factor_gt          0.1252
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.49765(16) -0.02489(11) 0.77649(8) 0.0476(3) Uani 1 1 d . . .
Cl Cl -0.07121(19) 0.27222(16) 0.55113(9) 0.0898(5) Uani 1 1 d . . .
O3 O 0.6596(4) -0.0831(3) 0.84178(19) 0.0594(7) Uani 1 1 d . . .
O2A O 0.4427(5) -0.1242(3) 0.6606(2) 0.0641(8) Uani 1 1 d . . .
O1A O 0.2476(4) -0.0241(3) 0.80008(19) 0.0538(7) Uani 1 1 d . . .
N3 N 0.5945(6) 0.1519(3) 0.7814(3) 0.0522(9) Uani 1 1 d . . .
O1 O 0.9433(4) 0.3678(3) 0.8597(2) 0.0671(8) Uani 1 1 d . . .
C3 C 0.4925(6) 0.2619(4) 0.7412(3) 0.0459(9) Uani 1 1 d . . .
C4 C 0.6008(6) 0.4150(4) 0.7654(3) 0.0480(9) Uani 1 1 d . . .
C7 C 0.8293(6) 0.4628(4) 0.8315(3) 0.0519(10) Uani 1 1 d . . .
C2 C 0.2845(6) 0.2216(5) 0.6751(3) 0.0553(10) Uani 1 1 d . . .
H2 H 0.2121 0.1205 0.6574 0.066 Uiso 1 1 calc R . .
C9 C 0.2086(6) 0.0635(5) 0.9021(3) 0.0651(11) Uani 1 1 d . . .
H9A H 0.0477 0.0546 0.9056 0.098 Uiso 1 1 calc R . .
H9B H 0.2646 0.1712 0.9155 0.098 Uiso 1 1 calc R . .
H9C H 0.2877 0.0229 0.9531 0.098 Uiso 1 1 calc R . .
C1 C 0.1856(7) 0.3295(5) 0.6358(3) 0.0590(11) Uani 1 1 d . . .
N1 N 1.1302(8) 0.6545(4) 0.9114(3) 0.0721(10) Uani 1 1 d . . .
C6 C 0.2849(8) 0.4783(5) 0.6593(3) 0.0690(12) Uani 1 1 d . . .
H6 H 0.2149 0.5504 0.6323 0.083 Uiso 1 1 calc R . .
C5 C 0.4912(7) 0.5203(5) 0.7239(3) 0.0651(11) Uani 1 1 d . . .
H5 H 0.5599 0.6223 0.7404 0.078 Uiso 1 1 calc R . .
C8 C 0.9202(7) 0.6230(5) 0.8605(3) 0.0656(11) Uani 1 1 d . . .
H8 H 0.8375 0.6993 0.8445 0.079 Uiso 1 1 calc R . .
N2 N 1.3116(8) 0.6734(5) 0.9532(3) 0.1011(14) Uani 1 1 d . . .
C10 C 0.6295(10) -0.1528(6) 0.6023(4) 0.0978(16) Uani 1 1 d . . .
H10A H 0.5722 -0.2150 0.5324 0.147 Uiso 1 1 calc R . .
H10B H 0.7360 -0.2074 0.6339 0.147 Uiso 1 1 calc R . .
H10C H 0.7052 -0.0553 0.6016 0.147 Uiso 1 1 calc R . .
HL H 0.723(6) 0.184(4) 0.815(3) 0.041(10) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.0464(6) 0.0417(6) 0.0539(7) 0.0162(5) 0.0005(5) 0.0032(4)
Cl 0.0664(8) 0.1251(11) 0.0844(9) 0.0482(8) -0.0108(6) 0.0218(7)
O3 0.0541(16) 0.0510(15) 0.0765(18) 0.0280(14) -0.0004(14) 0.0091(12)
O2A 0.0711(19) 0.0599(17) 0.0537(17) 0.0057(14) 0.0073(15) 0.0080(14)
O1A 0.0426(15) 0.0580(16) 0.0580(17) 0.0174(13) -0.0001(13) 0.0007(12)
N3 0.044(2) 0.0456(19) 0.067(2) 0.0230(17) -0.0060(18) 0.0032(16)
O1 0.0573(17) 0.0508(16) 0.094(2) 0.0278(16) -0.0034(15) 0.0079(14)
C3 0.048(2) 0.048(2) 0.047(2) 0.0182(18) 0.0104(18) 0.0123(18)
C4 0.055(2) 0.044(2) 0.051(2) 0.0191(18) 0.0120(19) 0.0157(18)
C7 0.057(2) 0.045(2) 0.057(3) 0.0160(19) 0.016(2) 0.009(2)
C2 0.056(2) 0.058(2) 0.056(2) 0.023(2) 0.005(2) 0.010(2)
C9 0.049(2) 0.078(3) 0.068(3) 0.020(2) 0.014(2) 0.009(2)
C1 0.056(2) 0.074(3) 0.056(3) 0.028(2) 0.012(2) 0.019(2)
N1 0.085(3) 0.053(2) 0.072(3) 0.0115(19) 0.012(2) -0.006(2)
C6 0.077(3) 0.069(3) 0.069(3) 0.032(2) 0.004(2) 0.028(3)
C5 0.077(3) 0.050(2) 0.073(3) 0.026(2) 0.007(2) 0.013(2)
C8 0.063(3) 0.049(3) 0.078(3) 0.015(2) -0.005(2) 0.005(2)
N2 0.088(3) 0.101(3) 0.097(4) 0.016(3) -0.003(3) -0.019(3)
C10 0.117(5) 0.100(4) 0.073(3) 0.012(3) 0.029(3) 0.014(3)

_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 1.453(2) . ?
P1 O1A 1.555(3) . ?
P1 O2A 1.555(3) . ?
P1 N3 1.633(3) . ?
Cl C1 1.739(4) . ?
O2A C10 1.436(5) . ?
O1A C9 1.442(4) . ?
N3 C3 1.398(4) . ?
O1 C7 1.240(4) . ?
C3 C2 1.392(5) . ?
C3 C4 1.408(5) . ?
C4 C5 1.393(5) . ?
C4 C7 1.492(5) . ?
C7 C8 1.427(5) . ?
C2 C1 1.368(5) . ?
C1 C6 1.355(6) . ?
N1 N2 1.130(5) . ?
N1 C8 1.317(5) . ?
C6 C5 1.375(6) . ?

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 O1A 117.05(15) . . ?
O3 P1 O2A 115.77(15) . . ?
O1A P1 O2A 97.46(15) . . ?
O3 P1 N3 109.04(17) . . ?
O1A P1 N3 108.51(15) . . ?
O2A P1 N3 108.24(16) . . ?
C10 O2A P1 118.0(3) . . ?
C9 O1A P1 118.3(2) . . ?
C3 N3 P1 130.8(3) . . ?
C2 C3 N3 120.8(3) . . ?
C2 C3 C4 118.7(3) . . ?
N3 C3 C4 120.5(3) . . ?
C5 C4 C3 118.2(3) . . ?
C5 C4 C7 120.6(3) . . ?
C3 C4 C7 121.1(3) . . ?
O1 C7 C8 119.6(4) . . ?
O1 C7 C4 122.2(3) . . ?
C8 C7 C4 118.1(3) . . ?
C1 C2 C3 120.6(4) . . ?
C6 C1 C2 121.8(4) . . ?
C6 C1 Cl 119.4(3) . . ?
C2 C1 Cl 118.8(3) . . ?
N2 N1 C8 176.4(5) . . ?
C1 C6 C5 118.6(4) . . ?
C6 C5 C4 122.1(4) . . ?
N1 C8 C7 114.8(4) . . ?

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
O3 P1 O2A C10 -57.1(3) . . . . ?
O1A P1 O2A C10 177.9(3) . . . . ?
N3 P1 O2A C10 65.6(3) . . . . ?
O3 P1 O1A C9 58.6(3) . . . . ?
O2A P1 O1A C9 -177.4(2) . . . . ?
N3 P1 O1A C9 -65.2(3) . . . . ?
O3 P1 N3 C3 -172.8(3) . . . . ?
O1A P1 N3 C3 -44.2(4) . . . . ?
O2A P1 N3 C3 60.5(4) . . . . ?
P1 N3 C3 C2 -8.4(5) . . . . ?
P1 N3 C3 C4 172.8(3) . . . . ?
C2 C3 C4 C5 1.6(5) . . . . ?
N3 C3 C4 C5 -179.6(3) . . . . ?
C2 C3 C4 C7 -176.9(3) . . . . ?
N3 C3 C4 C7 1.8(5) . . . . ?
C5 C4 C7 O1 -171.4(3) . . . . ?
C3 C4 C7 O1 7.1(5) . . . . ?
C5 C4 C7 C8 6.8(5) . . . . ?
C3 C4 C7 C8 -174.6(3) . . . . ?
N3 C3 C2 C1 -179.9(3) . . . . ?
C4 C3 C2 C1 -1.1(5) . . . . ?
C3 C2 C1 C6 0.0(6) . . . . ?
C3 C2 C1 Cl 178.6(3) . . . . ?
C2 C1 C6 C5 0.5(6) . . . . ?
Cl C1 C6 C5 -178.1(3) . . . . ?
C1 C6 C5 C4 0.2(6) . . . . ?
C3 C4 C5 C6 -1.2(6) . . . . ?
C7 C4 C5 C6 177.4(4) . . . . ?
N2 N1 C8 C7 18(8) . . . . ?
O1 C7 C8 N1 3.8(6) . . . . ?
C4 C7 C8 N1 -174.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.050
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
_chemical_properties_physical    
'Air-sensitive, Moisture-sensitive, Heat-sensitive, Light-sensitive, Photo-sensitive'
