# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_anpm122a1

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 N O3 P'
_chemical_formula_sum            'C18 H14 N O3 P'
_chemical_formula_weight         323.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.075(6)
_cell_length_b                   11.026(6)
_cell_length_c                   16.317(8)
_cell_angle_alpha                90
_cell_angle_beta                 119.16(3)
_cell_angle_gamma                90
_cell_volume                     1582.9(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1298
_cell_measurement_theta_min      3
_cell_measurement_theta_max      31

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.188
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'MAR345 with image plate detector'
_diffrn_measurement_method       'psi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14640
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.315
_diffrn_reflns_theta_max         32.476
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measured_fraction_theta_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_point_group_measured_fraction_full 0.958
_reflns_number_total             5002
_reflns_number_gt                3311
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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       'MARXDS (Claudio Klein, 2005)'
_computing_cell_refinement       'AUTOMAR (Claudio Klein, 2007)'
_computing_data_reduction        'MARSCALE (Claudio Klein, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP (Brueggermann and Smith, 1990)'
_computing_publication_material  'PLATON (Spek, 1990)'

_refine_special_details          
;
 Regarding the crystal refinement parameter, for the structural
 resolution, it has been  considered only reflections that have
 a value max of theta = 25° (ACTA 50). Reflections between 25°
 and 32° have not been taken into account due to the poor quality
 of the reflections over this value. The poor quality of reflections
 could be due to the fact that the crystal does not diffract very
 well and to the kind of detector (image plate with spindle axis
 only) that was used. Other attempts of crystallization were done,
 but no single crystals of better quality were obtained. 
 The displacement parameters of some lengths in the direction of
 the bond are restrained to be equal within an effective standard
 deviation (DELU sentences)  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0589P)²]
 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     SHELXL
_refine_ls_extinction_coef       0.0077(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5002
_refine_ls_number_parameters     209
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1338
_refine_ls_wR_factor_gt          0.1189
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.074
_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 0.83624(5) 0.77958(3) 0.81683(3) 0.04675(13) Uani 1 1 d . . . . .
O1 O 0.73597(12) 0.85020(10) 0.84221(8) 0.0552(3) Uani 1 1 d . . . . .
O2 O 0.87351(17) 1.04596(12) 0.78284(10) 0.0766(4) Uani 1 1 d . . . . .
O3 O 0.64062(18) 1.09139(13) 0.68536(12) 0.0895(5) Uani 1 1 d . . . . .
N1 N 0.75249(18) 1.02658(13) 0.71238(12) 0.0627(4) Uani 1 1 d . U . . .
C1 C 0.79126(17) 0.80726(14) 0.69596(11) 0.0517(4) Uani 1 1 d . . . . .
C2 C 0.74341(19) 0.92063(16) 0.65431(11) 0.0575(4) Uani 1 1 d . U . . .
C3 C 0.6902(2) 0.9420(2) 0.56017(13) 0.0711(5) Uani 1 1 d . . . . .
H3 H 0.6560 1.0185 0.5346 0.085 Uiso 1 1 calc R U . . .
C4 C 0.6891(2) 0.8461(2) 0.50429(13) 0.0788(6) Uani 1 1 d . . . . .
H4 H 0.6545 0.8585 0.4407 0.095 Uiso 1 1 calc R U . . .
C5 C 0.7385(2) 0.7341(2) 0.54248(13) 0.0719(5) Uani 1 1 d . . . . .
H5 H 0.7393 0.6710 0.5050 0.086 Uiso 1 1 calc R U . . .
C6 C 0.78781(19) 0.71363(16) 0.63713(12) 0.0583(4) Uani 1 1 d . . . . .
H6 H 0.8190 0.6362 0.6617 0.070 Uiso 1 1 calc R U . . .
C7 C 0.80699(17) 0.61920(13) 0.81978(11) 0.0492(3) Uani 1 1 d . . . . .
C8 C 0.65707(19) 0.57682(16) 0.77150(12) 0.0590(4) Uani 1 1 d . . . . .
H8 H 0.5784 0.6314 0.7384 0.071 Uiso 1 1 calc R U . . .
C9 C 0.6240(2) 0.45585(17) 0.77210(14) 0.0679(5) Uani 1 1 d . . . . .
H9 H 0.5241 0.4285 0.7393 0.082 Uiso 1 1 calc R U . . .
C10 C 0.7414(2) 0.37558(17) 0.82221(15) 0.0766(6) Uani 1 1 d . . . . .
H10 H 0.7203 0.2936 0.8227 0.092 Uiso 1 1 calc R U . . .
C11 C 0.8889(2) 0.41567(16) 0.87134(16) 0.0776(6) Uani 1 1 d . . . . .
H11 H 0.9666 0.3607 0.9054 0.093 Uiso 1 1 calc R U . . .
C12 C 0.9228(2) 0.53711(14) 0.87059(13) 0.0603(4) Uani 1 1 d . . . . .
H12 H 1.0230 0.5637 0.9040 0.072 Uiso 1 1 calc R U . . .
C13 C 1.03572(17) 0.81189(13) 0.89008(11) 0.0480(3) Uani 1 1 d . U . . .
C14 C 1.0828(2) 0.86279(14) 0.97809(11) 0.0549(4) Uani 1 1 d . . . . .
H14 H 1.0126 0.8752 0.9988 0.066 Uiso 1 1 calc R U . . .
C15 C 1.2335(2) 0.89507(17) 1.03510(13) 0.0646(4) Uani 1 1 d . . . . .
H15 H 1.2641 0.9296 1.0936 0.078 Uiso 1 1 calc R U . . .
C16 C 1.3384(2) 0.87586(16) 1.00500(14) 0.0683(5) Uani 1 1 d . . . . .
H16 H 1.4397 0.8968 1.0437 0.082 Uiso 1 1 calc R U . . .
C17 C 1.2938(2) 0.82568(18) 0.91770(14) 0.0701(5) Uani 1 1 d . . . . .
H17 H 1.3646 0.8132 0.8975 0.084 Uiso 1 1 calc R U . . .
C18 C 1.14297(19) 0.79407(15) 0.86057(13) 0.0591(4) Uani 1 1 d . U . . .
H18 H 1.1128 0.7605 0.8018 0.071 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 1.4854(12) . ?
P1 C7 1.7973(18) . ?
P1 C13 1.804(2) . ?
P1 C1 1.8214(19) . ?
O2 N1 1.220(2) . ?
O3 N1 1.221(2) . ?
N1 C2 1.479(2) . ?
C1 C2 1.392(2) . ?
C1 C6 1.399(2) . ?
C2 C3 1.378(2) . ?
C3 C4 1.393(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.363(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.388(2) . ?
C7 C8 1.400(2) . ?
C8 C9 1.376(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.381(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.392(2) . ?
C13 C18 1.395(2) . ?
C14 C15 1.386(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.385(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

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 C7 111.44(7) . . ?
O1 P1 C13 113.66(8) . . ?
C7 P1 C13 108.72(7) . . ?
O1 P1 C1 111.71(7) . . ?
C7 P1 C1 103.68(7) . . ?
C13 P1 C1 107.06(8) . . ?
O2 N1 O3 124.10(18) . . ?
O2 N1 C2 117.62(14) . . ?
O3 N1 C2 118.23(16) . . ?
C2 C1 C6 116.16(16) . . ?
C2 C1 P1 121.56(13) . . ?
C6 C1 P1 121.96(13) . . ?
C3 C2 C1 123.47(18) . . ?
C3 C2 N1 116.64(17) . . ?
C1 C2 N1 119.87(15) . . ?
C2 C3 C4 118.35(19) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C5 C4 C3 120.24(18) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.54(19) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 121.19(18) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
C12 C7 C8 118.76(15) . . ?
C12 C7 P1 123.82(13) . . ?
C8 C7 P1 117.34(12) . . ?
C9 C8 C7 121.19(17) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C8 C9 C10 119.01(18) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C11 C10 C9 120.68(18) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.54(18) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 119.80(17) . . ?
C11 C12 H12 120.1 . . ?
C7 C12 H12 120.1 . . ?
C14 C13 C18 118.76(15) . . ?
C14 C13 P1 118.20(12) . . ?
C18 C13 P1 122.95(13) . . ?
C15 C14 C13 120.44(17) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 119.99(18) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.42(18) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C18 119.54(18) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C13 120.85(16) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?

_refine_diff_density_max         0.164
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.034

_shelxl_version_number           2012-9

_database_code_depnum_ccdc_archive 'CCDC 990187'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_criqm63

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 N O3 P'
_chemical_formula_sum            'C18 H14 N O3 P'
_chemical_formula_weight         323.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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                   18.635(9)
_cell_length_b                   10.871(4)
_cell_length_c                   16.459(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.05(2)
_cell_angle_gamma                90.00
_cell_volume                     3188(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    192
_cell_measurement_theta_min      3
_cell_measurement_theta_max      31

_exptl_crystal_description       needles
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'MAR345 with image plate detector'
_diffrn_measurement_method       'phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12357
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         31.83
_reflns_number_total             4195
_reflns_number_gt                3596
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'MARXDS (Claudio Klein, 2005)'
_computing_cell_refinement       'AUTOMAR (Claudio Klein, 2007)'
_computing_data_reduction        'MARSCALE (Claudio Klein, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP (Brueggermann and Smith, 1990)'
_computing_publication_material  'PLATON (Spek, 1990)'


_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)+(0.0409P)²+4.6055P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4195
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0793
_refine_ls_wR_factor_ref         0.1669
_refine_ls_wR_factor_gt          0.1557
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_restrained_S_all      1.205
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P P 0.15514(4) 0.46309(7) 0.10772(4) 0.04793(19) Uani 1 1 d . . .
O1 O 0.10544(10) 0.39250(18) 0.03619(11) 0.0562(5) Uani 1 1 d . . .
O2 O 0.05986(16) 0.1438(2) 0.15247(17) 0.0910(8) Uani 1 1 d . . .
O3 O 0.17384(15) 0.1901(2) 0.15636(16) 0.0835(7) Uani 1 1 d . . .
N1 N 0.11572(16) 0.2093(2) 0.17449(16) 0.0662(7) Uani 1 1 d . . .
C1 C 0.13402(14) 0.4339(3) 0.20769(16) 0.0506(6) Uani 1 1 d . . .
C2 C 0.11354(15) 0.3168(3) 0.22860(17) 0.0563(6) Uani 1 1 d . . .
C3 C 0.09066(17) 0.2942(3) 0.29969(18) 0.0689(8) Uani 1 1 d . . .
H3 H 0.0765 0.2157 0.3113 0.083 Uiso 1 1 calc R . .
C4 C 0.08935(19) 0.3919(4) 0.35340(19) 0.0778(10) Uani 1 1 d . . .
H4 H 0.0743 0.3785 0.4018 0.093 Uiso 1 1 calc R . .
C5 C 0.10990(18) 0.5077(4) 0.33620(19) 0.0706(9) Uani 1 1 d . . .
H5 H 0.1095 0.5720 0.3733 0.085 Uiso 1 1 calc R . .
C6 C 0.13133(16) 0.5293(3) 0.26347(17) 0.0598(7) Uani 1 1 d . . .
H6 H 0.1441 0.6086 0.2517 0.072 Uiso 1 1 calc R . .
C7 C 0.14370(14) 0.6269(3) 0.09130(15) 0.0494(6) Uani 1 1 d . . .
C8 C 0.07008(16) 0.6731(3) 0.06430(17) 0.0588(7) Uani 1 1 d . . .
H8 H 0.0297 0.6208 0.0604 0.071 Uiso 1 1 calc R . .
C9 C 0.0575(2) 0.7960(3) 0.0435(2) 0.0707(9) Uani 1 1 d . . .
H9 H 0.0086 0.8258 0.0255 0.085 Uiso 1 1 calc R . .
C10 C 0.1170(2) 0.8751(3) 0.0494(2) 0.0801(10) Uani 1 1 d . . .
H10 H 0.1081 0.9579 0.0360 0.096 Uiso 1 1 calc R . .
C11 C 0.1891(2) 0.8315(3) 0.0749(3) 0.0808(10) Uani 1 1 d . . .
H11 H 0.2290 0.8846 0.0782 0.097 Uiso 1 1 calc R . .
C12 C 0.20293(17) 0.7080(3) 0.0959(2) 0.0651(7) Uani 1 1 d . . .
H12 H 0.2521 0.6792 0.1132 0.078 Uiso 1 1 calc R . .
C13 C 0.25338(14) 0.4291(2) 0.12731(15) 0.0496(6) Uani 1 1 d . . .
C14 C 0.27729(15) 0.3851(3) 0.06027(17) 0.0566(7) Uani 1 1 d . . .
H14 H 0.2431 0.3778 0.0065 0.068 Uiso 1 1 calc R . .
C15 C 0.35147(17) 0.3519(3) 0.0728(2) 0.0663(8) Uani 1 1 d . . .
H15 H 0.3669 0.3216 0.0278 0.080 Uiso 1 1 calc R . .
C16 C 0.40225(17) 0.3641(3) 0.1520(2) 0.0715(9) Uani 1 1 d . . .
H16 H 0.4522 0.3427 0.1604 0.086 Uiso 1 1 calc R . .
C17 C 0.37942(18) 0.4078(4) 0.2187(2) 0.0753(9) Uani 1 1 d . . .
H17 H 0.4141 0.4159 0.2721 0.090 Uiso 1 1 calc R . .
C18 C 0.30539(16) 0.4399(3) 0.20697(18) 0.0643(8) Uani 1 1 d . . .
H18 H 0.2903 0.4688 0.2526 0.077 Uiso 1 1 calc R . .


_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
P O1 1.4809(19) . ?
P C13 1.802(3) . ?
P C7 1.804(3) . ?
P C1 1.828(3) . ?
O2 N1 1.225(3) . ?
O3 N1 1.223(3) . ?
N1 C2 1.477(4) . ?
C1 C6 1.395(4) . ?
C1 C2 1.401(4) . ?
C2 C3 1.380(4) . ?
C3 C4 1.386(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.397(4) . ?
C7 C8 1.405(4) . ?
C8 C9 1.382(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.385(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.369(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.392(5) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.388(4) . ?
C13 C14 1.390(4) . ?
C14 C15 1.384(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.374(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?

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 P C13 113.69(12) . . ?
O1 P C7 111.92(12) . . ?
C13 P C7 107.37(12) . . ?
O1 P C1 112.09(12) . . ?
C13 P C1 106.20(12) . . ?
C7 P C1 105.00(12) . . ?
O3 N1 O2 124.4(3) . . ?
O3 N1 C2 117.7(3) . . ?
O2 N1 C2 117.9(3) . . ?
C6 C1 C2 116.7(2) . . ?
C6 C1 P 121.5(2) . . ?
C2 C1 P 121.7(2) . . ?
C3 C2 C1 123.0(3) . . ?
C3 C2 N1 116.1(3) . . ?
C1 C2 N1 120.9(2) . . ?
C2 C3 C4 118.2(3) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C5 C4 C3 120.9(3) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 121.1(3) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C12 C7 C8 118.3(3) . . ?
C12 C7 P 123.9(2) . . ?
C8 C7 P 117.5(2) . . ?
C9 C8 C7 120.2(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C11 C10 C9 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 120.2(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 120.7(3) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
C18 C13 C14 118.8(3) . . ?
C18 C13 P 122.9(2) . . ?
C14 C13 P 118.3(2) . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 119.7(3) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.5(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C13 120.2(3) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.770
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.060
_database_code_depnum_ccdc_archive 'CCDC 990188'
