#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/98/1519861.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_1519861
loop_
_publ_author_name
'Besli, S.'
'Kilic, A.'
'Davies, David B.'
'Coles, Simon J.'
'Coles, Simon J.'
'Hursthouse, Michael B.'
_publ_section_title
;
 C18H25ClN5O2P3
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              298
_journal_year                    2007
_chemical_formula_sum            'C18 H25 Cl N5 O2 P3'
_chemical_formula_weight         471.79
_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                 109.2280(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.7832(2)
_cell_length_b                   10.0420(2)
_cell_length_c                   11.5984(2)
_cell_measurement_reflns_used    9129
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1075.90(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 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15393
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.426
_exptl_absorpt_correction_T_max  0.9196
_exptl_absorpt_correction_T_min  0.8827
_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    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.216
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.51(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4883
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.227
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0752P)²+0.5374P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1012
_reflns_number_gt                4795
_reflns_number_total             4883
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-298.cif
_cod_data_source_block           2007src0259
_cod_depositor_comments
;
Citation :
Besli, S and Kilic, A. and Davies, David B. and Coles, Simon J. and 
Coles, Simon J. and Hursthouse, Michael B. (2007) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/298)

More at:
http://ecrystals.chem.soton.ac.uk/298/

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               1519861
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 0.2688(3) 0.4122(2) 0.9245(2) 0.0187(5) Uani 1 1 d . . .
H1A H 0.2380 0.3514 0.9785 0.022 Uiso 1 1 calc R . .
H1B H 0.1917 0.4120 0.8437 0.022 Uiso 1 1 calc R . .
C2 C 0.2820(3) 0.5529(3) 0.9774(2) 0.0205(5) Uani 1 1 d . . .
H2A H 0.1980 0.5687 1.0052 0.025 Uiso 1 1 calc R . .
H2B H 0.3700 0.5562 1.0505 0.025 Uiso 1 1 calc R . .
C3 C 0.2899(3) 0.6676(2) 0.8935(2) 0.0179(5) Uani 1 1 d . . .
H3A H 0.2168 0.6538 0.8119 0.021 Uiso 1 1 calc R . .
H3B H 0.2668 0.7522 0.9269 0.021 Uiso 1 1 calc R . .
C4 C 0.4341(4) 0.8745(3) 0.6603(4) 0.0490(10) Uani 1 1 d . . .
H4A H 0.4794 0.9024 0.7464 0.059 Uiso 1 1 calc R A 1
H4B H 0.3515 0.9347 0.6216 0.059 Uiso 1 1 calc R A 1
C5 C 0.5569(4) 0.8856(5) 0.5857(4) 0.0433(16) Uani 0.719(8) 1 d P B 1
H5A H 0.6402 0.8265 0.6255 0.052 Uiso 0.719(8) 1 calc PR B 1
H5B H 0.5120 0.8556 0.5002 0.052 Uiso 0.719(8) 1 calc PR B 1
C5' C 0.5597(7) 0.9394(7) 0.6783(6) 0.0058(18) Uani 0.281(8) 1 d PU B 2
H5'1 H 0.6360 0.8713 0.7099 0.007 Uiso 0.281(8) 1 calc PR B 2
H5'2 H 0.5689 1.0008 0.7473 0.007 Uiso 0.281(8) 1 calc PR B 2
C6 C 0.6068(5) 1.0204(4) 0.5872(4) 0.0536(10) Uani 1 1 d . . .
H6A H 0.5291 1.0770 0.5333 0.064 Uiso 1 1 calc R B 1
H6B H 0.6357 1.0570 0.6710 0.064 Uiso 1 1 calc R B 1
C7 C 0.8034(2) 0.4457(3) 0.70953(19) 0.0148(4) Uani 1 1 d . B .
C8 C 0.8625(3) 0.5578(3) 0.6722(3) 0.0263(6) Uani 1 1 d . . .
H8 H 0.8449 0.6441 0.6978 0.032 Uiso 1 1 calc R . .
C9 C 0.9471(3) 0.5426(4) 0.5976(3) 0.0370(7) Uani 1 1 d . . .
H9 H 0.9866 0.6191 0.5721 0.044 Uiso 1 1 calc R . .
C10 C 0.9744(3) 0.4189(4) 0.5600(2) 0.0349(8) Uani 1 1 d . . .
H10 H 1.0335 0.4097 0.5099 0.042 Uiso 1 1 calc R . .
C11 C 0.9153(3) 0.3074(4) 0.5957(2) 0.0310(7) Uani 1 1 d . . .
H11 H 0.9334 0.2217 0.5691 0.037 Uiso 1 1 calc R . .
C12 C 0.8292(3) 0.3198(3) 0.6704(2) 0.0212(5) Uani 1 1 d . . .
H12 H 0.7886 0.2430 0.6944 0.025 Uiso 1 1 calc R . .
C13 C 0.8346(2) 0.4576(2) 0.96388(19) 0.0122(4) Uani 1 1 d . B .
C14 C 0.9464(2) 0.3644(3) 0.9915(2) 0.0164(4) Uani 1 1 d . . .
H14 H 0.9578 0.3092 0.9288 0.020 Uiso 1 1 calc R . .
C15 C 1.0413(2) 0.3519(3) 1.1102(2) 0.0217(5) Uani 1 1 d . . .
H15 H 1.1172 0.2882 1.1283 0.026 Uiso 1 1 calc R . .
C16 C 1.0255(3) 0.4326(3) 1.2024(2) 0.0269(6) Uani 1 1 d . . .
H16 H 1.0909 0.4246 1.2834 0.032 Uiso 1 1 calc R . .
C17 C 0.9138(3) 0.5250(3) 1.1757(2) 0.0295(6) Uani 1 1 d . . .
H17 H 0.9022 0.5796 1.2387 0.035 Uiso 1 1 calc R . .
C18 C 0.8182(3) 0.5377(3) 1.0562(2) 0.0220(5) Uani 1 1 d . . .
H18 H 0.7420 0.6011 1.0381 0.026 Uiso 1 1 calc R . .
N1 N 0.36099(19) 0.49478(19) 0.70932(16) 0.0111(3) Uani 1 1 d . B .
N2 N 0.6268(2) 0.60951(19) 0.79362(18) 0.0135(4) Uani 1 1 d . B .
N3 N 0.5982(2) 0.33554(18) 0.79820(18) 0.0131(4) Uani 1 1 d . B .
N4 N 0.4030(2) 0.3598(2) 0.90989(19) 0.0166(4) Uani 1 1 d . . .
N5 N 0.3831(2) 0.7394(2) 0.6559(2) 0.0165(4) Uani 1 1 d . B .
O1 O 0.43306(17) 0.67723(16) 0.88124(14) 0.0139(3) Uani 1 1 d . B .
O2 O 0.7212(3) 1.0175(3) 0.54699(18) 0.0461(7) Uani 1 1 d . B .
H2 H 0.6985 0.9769 0.4800 0.069 Uiso 1 1 calc R . .
P1 P 0.43341(5) 0.36272(5) 0.78036(5) 0.01014(13) Uani 1 1 d . B .
P2 P 0.45595(6) 0.62596(5) 0.75840(5) 0.00930(12) Uani 1 1 d . . .
P3 P 0.70166(6) 0.46483(5) 0.81287(5) 0.01032(13) Uani 1 1 d . . .
Cl1 Cl 0.31959(6) 0.21212(6) 0.67400(6) 0.02193(14) Uani 1 1 d . . .
H5N H 0.349(4) 0.708(4) 0.587(3) 0.032(9) Uiso 1 1 d . . .
H4N H 0.449(4) 0.304(4) 0.957(3) 0.024(8) 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'
Cl Cl 0.1484 0.1585 '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
N4 C1 C2 114.5(2) . .
C3 C2 C1 117.2(2) . .
O1 C3 C2 111.36(19) . .
C5' C4 N5 138.6(4) . .
C5' C4 C5 44.3(3) . .
N5 C4 C5 109.8(3) . .
C6 C5 C4 110.5(3) . .
C4 C5' C6 128.5(5) . .
O2 C6 C5 107.1(4) . .
O2 C6 C5' 134.9(4) . .
C5 C6 C5' 47.5(4) . .
C12 C7 C8 119.5(2) . .
C12 C7 P3 120.74(18) . .
C8 C7 P3 119.7(2) . .
C9 C8 C7 119.8(3) . .
C10 C9 C8 121.0(3) . .
C9 C10 C11 119.6(2) . .
C10 C11 C12 120.6(3) . .
C7 C12 C11 119.5(3) . .
C18 C13 C14 119.5(2) . .
C18 C13 P3 119.68(17) . .
C14 C13 P3 120.63(17) . .
C15 C14 C13 120.4(2) . .
C14 C15 C16 120.1(2) . .
C17 C16 C15 119.8(2) . .
C16 C17 C18 120.1(2) . .
C13 C18 C17 120.1(2) . .
P1 N1 P2 113.06(10) . .
P2 N2 P3 121.36(12) . .
P1 N3 P3 116.78(12) . .
C1 N4 P1 122.71(17) . .
C4 N5 P2 124.6(2) . .
C3 O1 P2 119.13(14) . .
N3 P1 N1 118.09(10) . .
N3 P1 N4 111.43(11) . .
N1 P1 N4 107.86(11) . .
N3 P1 Cl1 106.38(8) . .
N1 P1 Cl1 104.05(7) . .
N4 P1 Cl1 108.45(9) . .
N3 P1 P2 94.05(7) . .
N1 P1 P2 33.54(7) . .
N4 P1 P2 98.75(8) . .
Cl1 P1 P2 136.31(3) . .
N2 P2 O1 104.36(9) . .
N2 P2 N1 116.22(10) . .
O1 P2 N1 110.24(9) . .
N2 P2 N5 115.42(11) . .
O1 P2 N5 105.59(10) . .
N1 P2 N5 104.58(11) . .
N2 P2 P1 89.17(7) . .
O1 P2 P1 101.16(6) . .
N1 P2 P1 33.40(6) . .
N5 P2 P1 136.92(8) . .
N2 P3 N3 117.95(10) . .
N2 P3 C7 109.24(11) . .
N3 P3 C7 107.92(11) . .
N2 P3 C13 108.67(11) . .
N3 P3 C13 107.16(10) . .
C7 P3 C13 105.16(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N4 1.476(3) .
C1 C2 1.529(3) .
C2 C3 1.526(3) .
C3 O1 1.457(3) .
C4 C5' 1.346(7) .
C4 N5 1.441(4) .
C4 C5 1.701(6) .
C5 C6 1.437(7) .
C5' C6 1.520(8) .
C6 O2 1.347(5) .
C7 C12 1.394(4) .
C7 C8 1.397(4) .
C7 P3 1.803(2) .
C8 C9 1.389(4) .
C9 C10 1.372(5) .
C10 C11 1.384(5) .
C11 C12 1.400(3) .
C13 C18 1.389(3) .
C13 C14 1.395(3) .
C13 P3 1.807(2) .
C14 C15 1.389(3) .
C15 C16 1.391(4) .
C16 C17 1.388(4) .
C17 C18 1.399(4) .
N1 P1 1.5984(19) .
N1 P2 1.6044(19) .
N2 P2 1.5931(19) .
N2 P3 1.609(2) .
N3 P1 1.5800(19) .
N3 P3 1.6204(19) .
N4 P1 1.625(2) .
N5 P2 1.631(2) .
O1 P2 1.5985(16) .
P1 Cl1 2.0357(8) .
P1 P2 2.6718(7) .
