#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/98/1519819.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1519819
loop_
_publ_author_name
'Tomkinson, N'
'Coles, Simon J.'
'Hursthouse, Michael B.'
_publ_section_title
;
 C18H22NO4P
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              321
_journal_year                    2007
_chemical_formula_sum            'C18 H22 N O4 P'
_chemical_formula_weight         347.34
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                107.8860(10)
_cell_angle_beta                 96.6450(10)
_cell_angle_gamma                99.433(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3400(2)
_cell_length_b                   10.7116(2)
_cell_length_c                   11.0362(3)
_cell_measurement_reflns_used    4078
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     910.99(4)
_computing_cell_refinement       'DENZO, COLLECT'
_computing_data_reduction        'DENZO, COLLECT'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD Area Detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20942
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.46
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  0.9504
_exptl_absorpt_correction_T_min  0.9072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, G.M., 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4157
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0398P)²+0.3915P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0899
_reflns_number_gt                3622
_reflns_number_total             4157
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-321.cif
_cod_data_source_block           2007src0701
_cod_depositor_comments
;
Citation :
Tomkinson, N and Coles, Simon J. and Hursthouse, Michael B. (2007) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/321)

More at:
http://ecrystals.chem.soton.ac.uk/321/

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 3392 2015-05-12 13:50:21Z andrius 
;
_cod_original_cell_volume        910.98(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1519819
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C -0.02095(15) 0.30452(12) 0.22948(12) 0.0160(2) Uani 1 1 d . . .
C2 C -0.07288(16) 0.18556(13) 0.12457(13) 0.0218(3) Uani 1 1 d . . .
H2 H 0.0028 0.1526 0.0711 0.026 Uiso 1 1 calc R . .
C3 C -0.23601(18) 0.11533(15) 0.09853(14) 0.0277(3) Uani 1 1 d . . .
H3 H -0.2717 0.0342 0.0273 0.033 Uiso 1 1 calc R . .
C4 C -0.34653(17) 0.16396(16) 0.17682(15) 0.0284(3) Uani 1 1 d . . .
H4 H -0.4577 0.1158 0.1591 0.034 Uiso 1 1 calc R . .
C5 C -0.29539(17) 0.28225(16) 0.28053(14) 0.0269(3) Uani 1 1 d . . .
H5 H -0.3717 0.3153 0.3332 0.032 Uiso 1 1 calc R . .
C6 C -0.13260(16) 0.35282(14) 0.30783(13) 0.0208(3) Uani 1 1 d . . .
H6 H -0.0975 0.4336 0.3795 0.025 Uiso 1 1 calc R . .
C7 C 0.24266(15) 0.40891(12) 0.11261(12) 0.0168(3) Uani 1 1 d . . .
C8 C 0.30930(16) 0.30831(14) 0.03424(13) 0.0219(3) Uani 1 1 d . . .
H8 H 0.3275 0.2345 0.0605 0.026 Uiso 1 1 calc R . .
C9 C 0.34876(17) 0.31691(16) -0.08225(14) 0.0286(3) Uani 1 1 d . . .
H9 H 0.3944 0.2488 -0.1356 0.034 Uiso 1 1 calc R . .
C10 C 0.32189(18) 0.42425(16) -0.12108(14) 0.0298(3) Uani 1 1 d . . .
H10 H 0.3505 0.4299 -0.2004 0.036 Uiso 1 1 calc R . .
C11 C 0.25372(17) 0.52305(15) -0.04515(14) 0.0270(3) Uani 1 1 d . . .
H11 H 0.2344 0.5959 -0.0727 0.032 Uiso 1 1 calc R . .
C12 C 0.21340(16) 0.51576(13) 0.07157(13) 0.0212(3) Uani 1 1 d . . .
H12 H 0.1659 0.5834 0.1236 0.025 Uiso 1 1 calc R . .
C13 C 0.34230(19) 0.31853(14) 0.51604(13) 0.0259(3) Uani 1 1 d . . .
H13A H 0.3033 0.2707 0.5733 0.039 Uiso 1 1 calc R . .
H13B H 0.3213 0.4095 0.5447 0.039 Uiso 1 1 calc R . .
H13C H 0.4611 0.3234 0.5188 0.039 Uiso 1 1 calc R . .
C14 C 0.24473(15) 0.10946(13) 0.32477(12) 0.0171(3) Uani 1 1 d . . .
C15 C 0.20332(17) -0.10029(12) 0.37391(13) 0.0210(3) Uani 1 1 d . . .
C16 C 0.04492(18) -0.16490(15) 0.27606(16) 0.0304(3) Uani 1 1 d . . .
H16A H -0.0448 -0.1228 0.3078 0.046 Uiso 1 1 calc R . .
H16B H 0.0171 -0.2610 0.2638 0.046 Uiso 1 1 calc R . .
H16C H 0.0601 -0.1526 0.1934 0.046 Uiso 1 1 calc R . .
C17 C 0.1863(2) -0.12548(15) 0.50014(15) 0.0339(4) Uani 1 1 d . . .
H17A H 0.2859 -0.0770 0.5645 0.051 Uiso 1 1 calc R . .
H17B H 0.1719 -0.2218 0.4861 0.051 Uiso 1 1 calc R . .
H17C H 0.0900 -0.0939 0.5314 0.051 Uiso 1 1 calc R . .
C18 C 0.35424(17) -0.14465(14) 0.32401(15) 0.0272(3) Uani 1 1 d . . .
H18A H 0.3616 -0.1285 0.2419 0.041 Uiso 1 1 calc R . .
H18B H 0.3447 -0.2406 0.3105 0.041 Uiso 1 1 calc R . .
H18C H 0.4538 -0.0935 0.3874 0.041 Uiso 1 1 calc R . .
N1 N 0.25457(13) 0.24690(10) 0.38351(10) 0.0167(2) Uani 1 1 d . . .
O1 O 0.20208(12) 0.53700(9) 0.36183(9) 0.0234(2) Uani 1 1 d . . .
O2 O 0.31045(11) 0.31519(9) 0.29804(9) 0.0186(2) Uani 1 1 d . . .
O3 O 0.24234(12) 0.05713(10) 0.21078(9) 0.0246(2) Uani 1 1 d . . .
O4 O 0.22999(11) 0.04916(9) 0.41368(9) 0.0194(2) Uani 1 1 d . . .
P1 P 0.18414(4) 0.40454(3) 0.26253(3) 0.01499(10) Uani 1 1 d . . .
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'
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
C2 C1 C6 119.96(12) . .
C2 C1 P1 121.90(9) . .
C6 C1 P1 118.04(10) . .
C3 C2 C1 119.80(12) . .
C4 C3 C2 119.97(13) . .
C5 C4 C3 120.30(13) . .
C4 C5 C6 120.22(13) . .
C5 C6 C1 119.75(13) . .
C8 C7 C12 119.58(12) . .
C8 C7 P1 122.76(10) . .
C12 C7 P1 117.61(10) . .
C9 C8 C7 119.63(13) . .
C10 C9 C8 120.37(14) . .
C11 C10 C9 120.37(13) . .
C10 C11 C12 119.93(13) . .
C11 C12 C7 120.10(13) . .
O3 C14 O4 127.43(12) . .
O3 C14 N1 123.71(12) . .
O4 C14 N1 108.77(10) . .
O4 C15 C16 110.24(11) . .
O4 C15 C17 102.29(10) . .
C16 C15 C17 110.43(12) . .
O4 C15 C18 109.29(10) . .
C16 C15 C18 113.00(12) . .
C17 C15 C18 111.06(12) . .
C14 N1 O2 108.49(9) . .
C14 N1 C13 121.45(10) . .
O2 N1 C13 110.33(10) . .
N1 O2 P1 112.80(7) . .
C14 O4 C15 119.69(10) . .
O1 P1 O2 114.16(5) . .
O1 P1 C7 115.02(6) . .
O2 P1 C7 98.36(5) . .
O1 P1 C1 112.41(6) . .
O2 P1 C1 107.11(5) . .
C7 P1 C1 108.67(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3959(18) .
C1 C6 1.3972(18) .
C1 P1 1.7948(12) .
C2 C3 1.3931(19) .
C3 C4 1.390(2) .
C4 C5 1.384(2) .
C5 C6 1.3909(19) .
C7 C8 1.3975(18) .
C7 C12 1.3996(18) .
C7 P1 1.7902(13) .
C8 C9 1.389(2) .
C9 C10 1.386(2) .
C10 C11 1.381(2) .
C11 C12 1.3900(19) .
C13 N1 1.4637(17) .
C14 O3 1.2060(15) .
C14 O4 1.3365(15) .
C14 N1 1.3987(16) .
C15 O4 1.4947(15) .
C15 C16 1.5171(19) .
C15 C17 1.516(2) .
C15 C18 1.5195(19) .
N1 O2 1.4338(13) .
O1 P1 1.4745(9) .
O2 P1 1.6262(9) .
