# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and 
# The Centre National de la Recherche Scientifique, 2001
# CCDC Number: 440/232

data_global
_publ_requested_journal  'New Journal of Chemistry'

_publ_section_title 
;
CAMPHENE-DERIVED PRIMARY- AND HYDROXYMETHYL-PHOSPHINES
;

_publ_contact_author_name 'B K Nicholson'
_publ_contact_author_address
;
Chemistry Department
University of Waikato
Private Bag 3105
Hamilton
New Zealand
;
_publ_contact_author_email 'b.nicholson@waikato.ac.nz'
 
data_camp
 
_audit_creation_method            SHELXL
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_formula_moiety          ?
_chemical_formula_structural      ?
_chemical_formula_analytical      ?
_chemical_formula_sum             'C13 H26 Cl O3 P'
_chemical_formula_weight          296.76
_chemical_melting_point           ?
_chemical_compound_source         ?
 
loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'P'  'P'   0.1023   0.0942
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl'  'Cl'   0.1484   0.1585
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            monoclinic
_symmetry_space_group_name_H-M    P21/c
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    16.504(7)
_cell_length_b                    7.561(5)
_cell_length_c                    12.142(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  92.54(2)
_cell_angle_gamma                 90.00
_cell_volume                      1513.7(12)
_cell_formula_units_Z             4
_cell_measurement_temperature     130(2)
_cell_measurement_reflns_used     18
_cell_measurement_theta_min       5
_cell_measurement_theta_max       15
 
_exptl_crystal_description        needle
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.57
_exptl_crystal_size_mid           0.16
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.302
_exptl_crystal_density_method     ?
_exptl_crystal_F_000              640
_exptl_absorpt_coefficient_mu     0.357
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       130(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        'Nicolet R3 four-circle'
_diffrn_measurement_method        'omega scans'
_diffrn_standards_number          3
_diffrn_standards_interval_count  100
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             2798
_diffrn_reflns_av_R_equivalents   0.0272
_diffrn_reflns_av_sigmaI/netI     0.0688
_diffrn_reflns_limit_h_min        -19
_diffrn_reflns_limit_h_max        19
_diffrn_reflns_limit_k_min        -8
_diffrn_reflns_limit_k_max        0
_diffrn_reflns_limit_l_min        0
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          2.47
_diffrn_reflns_theta_max          25.00
_reflns_number_total              2657
_reflns_number_observed           1706
_reflns_observed_criterion        >2sigma(I)
 
_computing_data_collection        'SHELXTL'
_computing_cell_refinement        'SHELXTL'
_computing_data_reduction         'SHELXTL'
_computing_structure_solution     'SHELX97'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1993)'
_computing_molecular_graphics     'PLUTO'
_computing_publication_material   'SHELX97'
 
_refine_special_details
;
 Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^
 or flagged by the user for potential systematic errors.  Weighted R-factors
 wR and all goodnesses of fit S are based on F^2^, conventional R-factors R
 are based on F, with F set to zero for negative F^2^. The observed criterion
 of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F^2^ 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 w=1/[\s^2^(Fo^2^)+(0.0486P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     RIDING
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          2657
_refine_ls_number_parameters      163
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0927
_refine_ls_R_factor_obs           0.0467
_refine_ls_wR_factor_all          0.1100
_refine_ls_wR_factor_obs          0.0936
_refine_ls_goodness_of_fit_all    1.023
_refine_ls_goodness_of_fit_obs    1.104
_refine_ls_restrained_S_all       1.023
_refine_ls_restrained_S_obs       1.104
_refine_ls_shift/esd_max          0.001
_refine_ls_shift/esd_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_thermal_displace_type
 _atom_site_occupancy
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_group
Cl1 Cl 0.39940(5) 0.19648(12) 0.51269(7) 0.0311(2) Uani 1 d . .
P1 P 0.63607(5) 0.30161(12) 0.34632(6) 0.0186(2) Uani 1 d . .
O1 O 0.69089(13) 0.4503(3) 0.5367(2) 0.0301(6) Uani 1 d . .
H1 H 0.67497(13) 0.5556(3) 0.5402(2) 0.045 Uiso 1 calc R .
O2 O 0.47727(13) 0.3555(3) 0.3144(2) 0.0276(6) Uani 1 d . .
H2 H 0.45253(13) 0.3240(3) 0.3701(2) 0.041 Uiso 1 calc R .
O3 O 0.68006(15) 0.4669(3) 0.1701(2) 0.0355(7) Uani 1 d . .
H3 H 0.66477(15) 0.5505(3) 0.1287(2) 0.053 Uiso 1 calc R .
C1 C 0.8439(2) 0.2955(5) 0.3728(3) 0.0325(9) Uani 1 d . .
H1A H 0.8223(2) 0.4074(5) 0.4041(3) 0.039 Uiso 1 calc R .
C2 C 0.7889(2) 0.1353(5) 0.3847(3) 0.0253(8) Uani 1 d . .
H2A H 0.7754(2) 0.1292(5) 0.4641(3) 0.030 Uiso 1 calc R .
C3 C 0.8468(2) -0.0269(5) 0.3630(3) 0.0273(8) Uani 1 d . .
C4 C 0.9296(2) 0.0676(5) 0.3554(3) 0.0305(9) Uani 1 d . .
H4 H 0.9774(2) -0.0097(5) 0.3742(3) 0.037 Uiso 1 calc R .
C5 C 0.9349(2) 0.1650(5) 0.2443(3) 0.0399(10) Uani 1 d . .
H5A H 0.9896(2) 0.2155(5) 0.2358(3) 0.048 Uiso 1 calc R .
H5B H 0.9215(2) 0.0851(5) 0.1815(3) 0.048 Uiso 1 calc R .
C6 C 0.8707(2) 0.3119(5) 0.2531(3) 0.0405(10) Uani 1 d . .
H6A H 0.8244(2) 0.2923(5) 0.1997(3) 0.049 Uiso 1 calc R .
H6B H 0.8944(2) 0.4298(5) 0.2397(3) 0.049 Uiso 1 calc R .
C7 C 0.9218(2) 0.2264(5) 0.4325(3) 0.0388(10) Uani 1 d . .
H7A H 0.9678(2) 0.3100(5) 0.4291(3) 0.047 Uiso 1 calc R .
H7B H 0.9135(2) 0.1915(5) 0.5098(3) 0.047 Uiso 1 calc R .
C8 C 0.7077(2) 0.1314(4) 0.3170(3) 0.0202(7) Uani 1 d . .
H8A H 0.6817(2) 0.0154(4) 0.3289(3) 0.024 Uiso 1 calc R .
H8B H 0.7196(2) 0.1389(4) 0.2379(3) 0.024 Uiso 1 calc R .
C9 C 0.8494(2) -0.1520(5) 0.4609(3) 0.0421(10) Uani 1 d . .
H9A H 0.8650(2) -0.0862(5) 0.5281(3) 0.063 Uiso 1 calc R .
H9B H 0.8892(2) -0.2456(5) 0.4493(3) 0.063 Uiso 1 calc R .
H9C H 0.7957(2) -0.2048(5) 0.4685(3) 0.063 Uiso 1 calc R .
C10 C 0.8224(2) -0.1320(5) 0.2588(3) 0.0383(10) Uani 1 d . .
H10A H 0.8205(2) -0.0526(5) 0.1949(3) 0.058 Uiso 1 calc R .
H10B H 0.7688(2) -0.1849(5) 0.2670(3) 0.058 Uiso 1 calc R .
H10C H 0.8622(2) -0.2257(5) 0.2478(3) 0.058 Uiso 1 calc R .
C11 C 0.6272(2) 0.3432(5) 0.4928(3) 0.0253(8) Uani 1 d . .
H11A H 0.5747(2) 0.4021(5) 0.5047(3) 0.030 Uiso 1 calc R .
H11B H 0.6275(2) 0.2289(5) 0.5327(3) 0.030 Uiso 1 calc R .
C12 C 0.5371(2) 0.2291(4) 0.2918(3) 0.0246(8) Uani 1 d . .
H12A H 0.5389(2) 0.2115(4) 0.2112(3) 0.030 Uiso 1 calc R .
H12B H 0.5231(2) 0.1145(4) 0.3257(3) 0.030 Uiso 1 calc R .
C13 C 0.6619(2) 0.5072(4) 0.2804(2) 0.0225(7) Uani 1 d . .
H13A H 0.6158(2) 0.5909(4) 0.2816(2) 0.027 Uiso 1 calc R .
H13B H 0.7095(2) 0.5621(4) 0.3194(2) 0.027 Uiso 1 calc R .
 
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
Cl1 0.0400(5) 0.0315(5) 0.0223(5) -0.0023(4) 0.0077(4) -0.0046(5)
P1 0.0203(4) 0.0217(5) 0.0141(4) -0.0001(4) 0.0022(3) -0.0007(4)
O1 0.0318(13) 0.0359(15) 0.0220(13) -0.0075(12) -0.0054(11) 0.0021(12)
O2 0.0228(12) 0.0296(13) 0.0305(13) 0.0063(12) 0.0041(10) 0.0008(11)
O3 0.058(2) 0.0289(15) 0.0210(13) 0.0055(12) 0.0140(12) 0.0089(13)
C1 0.026(2) 0.027(2) 0.046(2) -0.003(2) 0.005(2) 0.003(2)
C2 0.023(2) 0.030(2) 0.023(2) -0.003(2) 0.0031(14) 0.004(2)
C3 0.028(2) 0.027(2) 0.027(2) 0.003(2) 0.002(2) 0.004(2)
C4 0.021(2) 0.028(2) 0.043(2) -0.001(2) 0.003(2) 0.006(2)
C5 0.034(2) 0.035(2) 0.052(3) 0.010(2) 0.016(2) -0.003(2)
C6 0.032(2) 0.032(2) 0.057(3) 0.016(2) 0.007(2) -0.009(2)
C7 0.027(2) 0.041(2) 0.047(2) -0.008(2) -0.005(2) -0.003(2)
C8 0.026(2) 0.017(2) 0.018(2) 0.0003(14) 0.0035(14) -0.0018(14)
C9 0.040(2) 0.042(3) 0.044(2) 0.016(2) -0.001(2) 0.003(2)
C10 0.038(2) 0.030(2) 0.047(2) -0.009(2) 0.005(2) 0.003(2)
C11 0.030(2) 0.029(2) 0.017(2) -0.001(2) 0.0022(14) 0.002(2)
C12 0.026(2) 0.027(2) 0.021(2) -0.002(2) 0.0030(14) -0.006(2)
C13 0.033(2) 0.022(2) 0.013(2) 0.0010(15) 0.0021(14) 0.0017(15)
 
_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 C8 1.794(3) . ?
P1 C13 1.808(3) . ?
P1 C11 1.819(3) . ?
P1 C12 1.820(3) . ?
O1 C11 1.412(4) . ?
O2 C12 1.410(4) . ?
O3 C13 1.419(3) . ?
C1 C2 1.524(5) . ?
C1 C7 1.539(5) . ?
C1 C6 1.543(5) . ?
C2 C8 1.542(4) . ?
C2 C3 1.584(5) . ?
C3 C9 1.518(5) . ?
C3 C10 1.533(5) . ?
C3 C4 1.548(5) . ?
C4 C7 1.532(5) . ?
C4 C5 1.542(5) . ?
C5 C6 1.542(5) . ?
 
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
C8 P1 C13 111.0(2) . . ?
C8 P1 C11 113.6(2) . . ?
C13 P1 C11 108.4(2) . . ?
C8 P1 C12 107.5(2) . . ?
C13 P1 C12 108.9(2) . . ?
C11 P1 C12 107.33(15) . . ?
C2 C1 C7 100.0(3) . . ?
C2 C1 C6 110.5(3) . . ?
C7 C1 C6 101.7(3) . . ?
C1 C2 C8 118.1(3) . . ?
C1 C2 C3 103.5(3) . . ?
C8 C2 C3 114.4(3) . . ?
C9 C3 C10 108.7(3) . . ?
C9 C3 C4 109.9(3) . . ?
C10 C3 C4 113.0(3) . . ?
C9 C3 C2 110.4(3) . . ?
C10 C3 C2 113.6(3) . . ?
C4 C3 C2 101.1(3) . . ?
C7 C4 C5 99.8(3) . . ?
C7 C4 C3 103.1(3) . . ?
C5 C4 C3 110.9(3) . . ?
C6 C5 C4 102.6(3) . . ?
C5 C6 C1 103.5(3) . . ?
C4 C7 C1 94.0(3) . . ?
C2 C8 P1 116.4(2) . . ?
O1 C11 P1 112.2(2) . . ?
O2 C12 P1 110.5(2) . . ?
O3 C13 P1 107.3(2) . . ?
 
_refine_diff_density_max    0.345
_refine_diff_density_min   -0.216
_refine_diff_density_rms    0.060