#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/52/02/1520268.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_1520268
loop_
_publ_author_name
'Coles, Simon J.'
'Hursthouse, Michael B.'
'Davies, David B.'
'Kilic, A.'
'Yesilot, Serkan'
_publ_section_title
;
 C18H24N5O4P3
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              410
_journal_year                    2008
_chemical_formula_sum            'C18 H24 N5 O4 P3'
_chemical_formula_weight         467.33
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 96.5520(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.30730(10)
_cell_length_b                   17.6438(4)
_cell_length_c                   9.5481(2)
_cell_measurement_reflns_used    10282
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1055.62(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 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker-Nonius APEX2 Area Detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12391
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.15
_exptl_absorpt_coefficient_mu    0.318
_exptl_absorpt_correction_T_max  0.9874
_exptl_absorpt_correction_T_min  0.9333
_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    1.470
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4543
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0282
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0168P)²+0.6200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0645
_refine_ls_wR_factor_ref         0.0654
_reflns_number_gt                4430
_reflns_number_total             4543
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-410.cif
_cod_data_source_block           2008src0232
_cod_depositor_comments
;
Citation :
Coles, Simon J. and Hursthouse, Michael B. and Davies, David B. and 
Kilic, A. and Yesilot, Serkan (2008) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/410)

More at:
http://ecrystals.chem.soton.ac.uk/410/

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      P2(1)
_cod_database_code               1520268
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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 0.9402(3) 0.91402(11) 0.3254(2) 0.0163(4) Uani 1 1 d . . .
C2 C 0.7786(3) 0.95502(12) 0.3775(2) 0.0243(5) Uani 1 1 d . . .
H2 H 0.6360 0.9367 0.3667 0.029 Uiso 1 1 calc R . .
C3 C 0.8288(3) 1.02336(12) 0.4457(2) 0.0252(5) Uani 1 1 d . . .
H3 H 0.7189 1.0522 0.4805 0.030 Uiso 1 1 calc R . .
C4 C 1.0361(3) 1.04996(11) 0.4636(2) 0.0200(4) Uani 1 1 d . . .
H4 H 1.0688 1.0968 0.5102 0.024 Uiso 1 1 calc R . .
C5 C 1.1954(3) 1.00765(12) 0.4131(2) 0.0205(4) Uani 1 1 d . . .
H5 H 1.3384 1.0255 0.4258 0.025 Uiso 1 1 calc R . .
C6 C 1.1492(3) 0.93927(11) 0.3440(2) 0.0181(4) Uani 1 1 d . . .
H6 H 1.2596 0.9103 0.3101 0.022 Uiso 1 1 calc R . .
C7 C 0.4284(3) 0.88178(11) -0.0138(2) 0.0194(4) Uani 1 1 d . . .
C8 C 0.2386(3) 0.84485(11) 0.0005(2) 0.0206(4) Uani 1 1 d . . .
H8 H 0.2234 0.8150 0.0815 0.025 Uiso 1 1 calc R . .
C9 C 0.0707(3) 0.85229(13) -0.1064(2) 0.0261(5) Uani 1 1 d . . .
H9 H -0.0605 0.8271 -0.0985 0.031 Uiso 1 1 calc R . .
C10 C 0.0933(4) 0.89632(13) -0.2248(2) 0.0295(5) Uani 1 1 d . . .
H10 H -0.0226 0.9015 -0.2970 0.035 Uiso 1 1 calc R . .
C11 C 0.2856(4) 0.93256(13) -0.2369(2) 0.0314(5) Uani 1 1 d . . .
H11 H 0.3021 0.9620 -0.3182 0.038 Uiso 1 1 calc R . .
C12 C 0.4542(4) 0.92583(12) -0.1304(2) 0.0252(5) Uani 1 1 d . . .
H12 H 0.5854 0.9512 -0.1376 0.030 Uiso 1 1 calc R . .
C13 C 0.2123(3) 0.74290(12) 0.5376(2) 0.0203(4) Uani 1 1 d . . .
H13A H 0.0718 0.7254 0.5618 0.024 Uiso 1 1 calc R . .
H13B H 0.1996 0.7971 0.5108 0.024 Uiso 1 1 calc R . .
C14 C 0.3799(3) 0.73351(12) 0.6644(2) 0.0226(4) Uani 1 1 d . . .
H14A H 0.3402 0.7646 0.7437 0.027 Uiso 1 1 calc R . .
H14B H 0.3854 0.6798 0.6947 0.027 Uiso 1 1 calc R . .
C15 C 0.5968(3) 0.75768(12) 0.6278(2) 0.0225(4) Uani 1 1 d . . .
H15A H 0.5916 0.8114 0.5975 0.027 Uiso 1 1 calc R . .
H15B H 0.7032 0.7531 0.7120 0.027 Uiso 1 1 calc R . .
C16 C 1.0731(3) 0.60916(12) 0.0622(2) 0.0232(4) Uani 1 1 d . . .
H16A H 1.2117 0.5847 0.0934 0.028 Uiso 1 1 calc R . .
H16B H 1.1024 0.6586 0.0192 0.028 Uiso 1 1 calc R . .
C17 C 0.9473(3) 0.55952(12) -0.0472(2) 0.0238(4) Uani 1 1 d . . .
H17A H 1.0290 0.5532 -0.1290 0.029 Uiso 1 1 calc R . .
H17B H 0.9279 0.5088 -0.0063 0.029 Uiso 1 1 calc R . .
C18 C 0.7308(3) 0.59311(13) -0.0968(2) 0.0240(4) Uani 1 1 d . . .
H18A H 0.7506 0.6412 -0.1471 0.029 Uiso 1 1 calc R . .
H18B H 0.6513 0.5578 -0.1641 0.029 Uiso 1 1 calc R . .
N1 N 0.5300(3) 0.79640(9) 0.30218(17) 0.0165(3) Uani 1 1 d . . .
N2 N 0.5760(3) 0.64445(9) 0.27530(18) 0.0189(4) Uani 1 1 d . . .
N3 N 0.7380(3) 0.74228(9) 0.09116(18) 0.0191(4) Uani 1 1 d . . .
N4 N 0.2750(3) 0.69799(9) 0.41793(18) 0.0174(3) Uani 1 1 d . . .
N5 N 0.9548(3) 0.62201(10) 0.18678(19) 0.0190(3) Uani 1 1 d . . .
O1 O 0.9078(2) 0.84579(7) 0.25289(15) 0.0183(3) Uani 1 1 d . . .
O2 O 0.6021(2) 0.88168(8) 0.09166(14) 0.0190(3) Uani 1 1 d . . .
O3 O 0.66056(19) 0.71003(8) 0.51440(14) 0.0195(3) Uani 1 1 d . . .
O4 O 0.6053(2) 0.60774(8) 0.01980(15) 0.0201(3) Uani 1 1 d . . .
P1 P 0.68442(7) 0.81113(3) 0.18652(5) 0.01550(11) Uani 1 1 d . . .
P2 P 0.51106(7) 0.71306(3) 0.36849(5) 0.01452(10) Uani 1 1 d . . .
P3 P 0.71145(7) 0.65762(3) 0.14669(5) 0.01549(11) Uani 1 1 d . . .
H4N H 0.176(4) 0.6891(16) 0.349(3) 0.041(8) Uiso 1 1 d . . .
H5N H 0.943(4) 0.5805(15) 0.232(3) 0.027(7) Uiso 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
C6 C1 C2 120.95(18) . .
C6 C1 O1 115.22(16) . .
C2 C1 O1 123.83(17) . .
C1 C2 C3 118.86(19) . .
C4 C3 C2 120.99(19) . .
C3 C4 C5 119.25(19) . .
C4 C5 C6 120.88(18) . .
C1 C6 C5 119.04(18) . .
C12 C7 C8 121.78(19) . .
C12 C7 O2 115.17(18) . .
C8 C7 O2 122.91(18) . .
C7 C8 C9 118.60(19) . .
C8 C9 C10 120.6(2) . .
C11 C10 C9 119.7(2) . .
C10 C11 C12 120.2(2) . .
C7 C12 C11 119.1(2) . .
N4 C13 C14 109.46(16) . .
C15 C14 C13 110.46(17) . .
O3 C15 C14 109.97(16) . .
N5 C16 C17 111.51(16) . .
C18 C17 C16 111.84(17) . .
O4 C18 C17 112.25(17) . .
P1 N1 P2 120.37(10) . .
P2 N2 P3 121.20(10) . .
P1 N3 P3 119.36(11) . .
C13 N4 P2 117.91(13) . .
C16 N5 P3 113.99(14) . .
C1 O1 P1 126.91(12) . .
C7 O2 P1 126.00(12) . .
C15 O3 P2 116.31(12) . .
C18 O4 P3 117.57(12) . .
N1 P1 N3 117.89(9) . .
N1 P1 O2 109.91(8) . .
N3 P1 O2 110.56(9) . .
N1 P1 O1 111.89(8) . .
N3 P1 O1 106.63(8) . .
O2 P1 O1 98.16(7) . .
N2 P2 O3 107.51(9) . .
N2 P2 N1 116.20(9) . .
O3 P2 N1 108.16(8) . .
N2 P2 N4 109.90(9) . .
O3 P2 N4 102.12(8) . .
N1 P2 N4 111.88(8) . .
O4 P3 N2 106.98(8) . .
O4 P3 N3 108.45(8) . .
N2 P3 N3 118.53(9) . .
O4 P3 N5 105.36(8) . .
N2 P3 N5 109.28(9) . .
N3 P3 N5 107.48(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.384(3) .
C1 C2 1.388(3) .
C1 O1 1.392(2) .
C2 C3 1.390(3) .
C3 C4 1.381(3) .
C4 C5 1.382(3) .
C5 C6 1.390(3) .
C7 C12 1.382(3) .
C7 C8 1.383(3) .
C7 O2 1.401(2) .
C8 C9 1.390(3) .
C9 C10 1.392(3) .
C10 C11 1.388(4) .
C11 C12 1.390(3) .
C13 N4 1.481(2) .
C13 C14 1.523(3) .
C14 C15 1.512(3) .
C15 O3 1.463(2) .
C16 N5 1.492(3) .
C16 C17 1.516(3) .
C17 C18 1.514(3) .
C18 O4 1.460(2) .
N1 P1 1.5754(16) .
N1 P2 1.6107(16) .
N2 P2 1.5836(16) .
N2 P3 1.5911(17) .
N3 P1 1.5777(17) .
N3 P3 1.6002(17) .
N4 P2 1.6344(16) .
N5 P3 1.6622(17) .
O1 P1 1.5991(14) .
O2 P1 1.5911(14) .
O3 P2 1.5916(14) .
O4 P3 1.5829(14) .
