#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/58/4115847.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_4115847
loop_
_publ_author_name
'K. C. Kumara Swamy'
'Sudha Kumaraswamy'
'Praveen Kommana'
_publ_section_title
;
 Very Strong C-H...O, N-H...O, and O-H...O Hydrogen Bonds Involving a
 Cyclic Phosphate
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12642
_journal_page_last               12649
_journal_paper_doi               10.1021/ja010713x
_journal_volume                  123
_journal_year                    2001
_chemical_formula_sum            'C28.5 H38 N5 O4.5 P'
_chemical_formula_weight         553.61
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.66(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.312(3)
_cell_length_b                   14.871(3)
_cell_length_c                   14.950(9)
_cell_measurement_temperature    293(2)
_cell_volume                     2933(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0883
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6537
_diffrn_reflns_theta_full        26.45
_diffrn_reflns_theta_max         26.45
_diffrn_reflns_theta_min         1.37
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.9731
_exptl_absorpt_correction_T_min  0.9472
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_F_000             1180
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.753
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         6283
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1394
_refine_ls_R_factor_gt           0.0621
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0899P)²+0.0298P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.2200
_reflns_number_gt                2420
_reflns_number_total             6283
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja010713x_09.cif
_cod_data_source_block           compound6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0899P)^2^+0.0298P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0899P)^2^+0.0298P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_formula_sum        'C28.50 H38 N5 O4.50 P'
_cod_database_code               4115847
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-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_calc_flag
_atom_site_refinement_flags
P1 P 0.43743(10) 0.2500 0.81264(8) 0.0559(4) Uani 1 d S
O1 O 0.36615(16) 0.16521(15) 0.78907(14) 0.0577(6) Uani 1 d .
O2 O 0.5219(2) 0.2500 0.7579(2) 0.0607(9) Uani 1 d S
O3 O 0.4619(2) 0.2500 0.9122(2) 0.0622(9) Uani 1 d S
H3 H 0.4183 0.2781 0.9344 0.093 Uiso 0.50 calc PR
C1 C 0.3590(2) 0.1223(2) 0.7050(2) 0.0565(8) Uani 1 d .
C2 C 0.4041(3) 0.0385(2) 0.6991(2) 0.0607(9) Uani 1 d .
C3 C 0.3937(3) 0.0005(2) 0.6131(2) 0.0666(10) Uani 1 d .
H3 H 0.4238 -0.0550 0.6058 0.080 Uiso 1 calc R
C4 C 0.3406(3) 0.0414(3) 0.5380(2) 0.0668(10) Uani 1 d .
C5 C 0.2921(3) 0.1218(2) 0.5493(2) 0.0633(9) Uani 1 d .
H5 H 0.2536 0.1486 0.4999 0.076 Uiso 1 calc R
C6 C 0.2997(2) 0.1635(2) 0.6329(2) 0.0572(8) Uani 1 d .
C7 C 0.2428(3) 0.2500 0.6440(3) 0.0570(12) Uani 1 d S
H7A H 0.1819 0.2500 0.6005 0.068 Uiso 1 calc SR
H7B H 0.2217 0.2500 0.7037 0.068 Uiso 1 calc SR
C8 C 0.4607(3) -0.0118(2) 0.7813(3) 0.0704(10) Uani 1 d .
C9 C 0.4901(4) -0.1073(3) 0.7572(3) 0.0985(15) Uani 1 d .
H9A H 0.4308 -0.1391 0.7304 0.148 Uiso 1 calc R
H9B H 0.5193 -0.1381 0.8109 0.148 Uiso 1 calc R
H9C H 0.5386 -0.1048 0.7152 0.148 Uiso 1 calc R
C10 C 0.3915(4) -0.0223(3) 0.8549(3) 0.1032(16) Uani 1 d .
H10A H 0.3722 0.0360 0.8741 0.155 Uiso 1 calc R
H10B H 0.4271 -0.0541 0.9054 0.155 Uiso 1 calc R
H10C H 0.3320 -0.0555 0.8313 0.155 Uiso 1 calc R
C11 C 0.5583(3) 0.0369(3) 0.8191(3) 0.1030(16) Uani 1 d .
H11A H 0.5968 0.0504 0.7709 0.154 Uiso 1 calc R
H11B H 0.5976 -0.0009 0.8626 0.154 Uiso 1 calc R
H11C H 0.5418 0.0918 0.8477 0.154 Uiso 1 calc R
C12 C 0.3352(4) -0.0015(3) 0.4457(3) 0.0934(14) Uani 1 d .
H12A H 0.3230 0.0441 0.4001 0.140 Uiso 1 calc R
H12B H 0.2809 -0.0445 0.4380 0.140 Uiso 1 calc R
H12C H 0.3981 -0.0312 0.4404 0.140 Uiso 1 calc R
N1 N 0.7593(4) 0.2500 0.3581(3) 0.0786(15) Uani 1 d S
N2 N 0.8354(4) 0.2500 0.5069(3) 0.0725(13) Uani 1 d S
N3 N 0.7495(4) 0.2500 0.6347(3) 0.0736(13) Uani 1 d S
N4 N 0.5688(4) 0.2500 0.5878(3) 0.0771(14) Uani 1 d S
N5 N 0.5633(4) 0.2500 0.4386(3) 0.0728(12) Uani 1 d S
C13 C 0.7487(4) 0.2500 0.4431(3) 0.0642(14) Uani 1 d S
C14 C 0.8309(5) 0.2500 0.5952(4) 0.0758(16) Uani 1 d S
H14 H 0.8925 0.2500 0.6327 0.091 Uiso 1 calc SR
C15 C 0.6639(5) 0.2500 0.5730(4) 0.0653(14) Uani 1 d S
C16 C 0.5107(5) 0.2500 0.5057(4) 0.0814(17) Uani 1 d S
H16 H 0.4402 0.2500 0.4983 0.098 Uiso 1 calc SR
C17 C 0.6599(4) 0.2500 0.4792(4) 0.0636(13) Uani 1 d S
P2 P 0.03777(11) 0.2500 0.36975(9) 0.0741(5) Uani 1 d S
O4 O 0.10605(17) 0.16388(19) 0.36012(16) 0.0730(7) Uani 1 d .
O5 O -0.0496(2) 0.2500 0.2967(2) 0.0729(10) Uani 1 d S
O6 O 0.0183(3) 0.2500 0.4651(2) 0.0942(14) Uani 1 d S
C18 C 0.1176(3) 0.1250(3) 0.2765(2) 0.0672(10) Uani 1 d .
C19 C 0.0665(3) 0.0461(3) 0.2469(3) 0.0794(12) Uani 1 d .
C20 C 0.0861(3) 0.0134(3) 0.1650(3) 0.0885(13) Uani 1 d .
H20 H 0.0516 -0.0380 0.1428 0.106 Uiso 1 calc R
C21 C 0.1536(4) 0.0518(3) 0.1135(3) 0.0823(12) Uani 1 d .
C22 C 0.2043(3) 0.1277(3) 0.1472(3) 0.0706(10) Uani 1 d .
H22 H 0.2514 0.1541 0.1147 0.085 Uiso 1 calc R
C23 C 0.1872(3) 0.1655(3) 0.2279(2) 0.0627(9) Uani 1 d .
C24 C 0.2436(4) 0.2500 0.2613(4) 0.0659(14) Uani 1 d S
H24A H 0.3099 0.2500 0.2411 0.079 Uiso 1 calc SR
H24B H 0.2535 0.2500 0.3268 0.079 Uiso 1 calc SR
C25 C -0.0037(4) -0.0073(4) 0.3027(4) 0.1040(16) Uani 1 d .
C26 C 0.0541(5) -0.0315(4) 0.3930(4) 0.146(2) Uani 1 d .
H26A H 0.0713 0.0224 0.4270 0.219 Uiso 1 calc R
H26B H 0.1150 -0.0629 0.3842 0.219 Uiso 1 calc R
H26C H 0.0129 -0.0693 0.4253 0.219 Uiso 1 calc R
C27 C -0.0299(6) -0.1004(4) 0.2617(4) 0.180(3) Uani 1 d .
H27A H -0.0521 -0.1390 0.3067 0.270 Uiso 1 calc R
H27B H 0.0291 -0.1259 0.2409 0.270 Uiso 1 calc R
H27C H -0.0830 -0.0947 0.2119 0.270 Uiso 1 calc R
C28 C -0.1006(5) 0.0410(5) 0.3083(8) 0.270(6) Uani 1 d .
H28A H -0.1417 0.0063 0.3437 0.404 Uiso 1 calc R
H28B H -0.1362 0.0492 0.2487 0.404 Uiso 1 calc R
H28C H -0.0864 0.0986 0.3361 0.404 Uiso 1 calc R
C29 C 0.1721(4) 0.0099(4) 0.0248(3) 0.1173(17) Uani 1 d .
H29A H 0.2197 -0.0385 0.0362 0.176 Uiso 1 calc R
H29B H 0.1989 0.0545 -0.0120 0.176 Uiso 1 calc R
H29C H 0.1093 -0.0128 -0.0061 0.176 Uiso 1 calc R
N6 N -0.2758(5) 0.2500 -0.1515(3) 0.093(2) Uani 1 d S
N7 N -0.3498(4) 0.2500 -0.0119(4) 0.0775(15) Uani 1 d S
N8 N -0.2587(4) 0.2500 0.1320(3) 0.0835(15) Uani 1 d S
N9 N -0.0824(4) 0.2500 0.1184(3) 0.0876(16) Uani 1 d S
N10 N -0.0816(4) 0.2500 -0.0329(3) 0.0883(15) Uani 1 d S
C30 C -0.2630(5) 0.2500 -0.0636(4) 0.0793(16) Uani 1 d S
C31 C -0.3442(5) 0.2500 0.0763(5) 0.0868(18) Uani 1 d S
H31 H -0.4046 0.2500 0.1012 0.104 Uiso 1 calc SR
C32 C -0.1793(6) 0.2500 0.0857(4) 0.0752(16) Uani 1 d S
C33 C -0.0277(6) 0.2500 0.0485(4) 0.098(2) Uani 1 d S
H33 H 0.0428 0.2500 0.0568 0.118 Uiso 1 calc SR
C34 C -0.1747(5) 0.2500 -0.0100(4) 0.0867(18) Uani 1 d S
O7 O 0.2932(7) 0.2500 0.9934(5) 0.224(4) Uani 1 d S
C35 C 0.2074(9) 0.2500 0.9251(7) 0.198(5) Uani 1 d S
H35A H 0.1491 0.2716 0.9501 0.297 Uiso 0.50 calc PR
H35B H 0.1949 0.1899 0.9029 0.297 Uiso 0.50 calc PR
H35C H 0.2205 0.2885 0.8764 0.297 Uiso 0.50 calc PR
HN1A H 0.830(3) 0.2500 0.327(3) 0.050 Uiso 1 d S
HN1B H 0.713(4) 0.2500 0.331(3) 0.050 Uiso 1 d S
HN6A H -0.235(4) 0.2500 -0.181(3) 0.050 Uiso 1 d S
HN6B H -0.324(4) 0.2500 -0.179(3) 0.050 Uiso 1 d S
HN2 H 0.895(4) 0.2500 0.482(3) 0.050 Uiso 1 d S
HN4 H 0.551(3) 0.2500 0.639(3) 0.050 Uiso 1 d S
HN9 H -0.065(3) 0.2500 0.175(3) 0.050 Uiso 1 d S
HN7 H -0.408(4) 0.2500 -0.034(3) 0.050 Uiso 1 d S
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'
N N 0.0061 0.0033 '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
O2 P1 O3 118.4(2) . .
O2 P1 O1 110.70(11) . .
O3 P1 O1 105.52(12) . .
O2 P1 O1 110.70(11) . 4_565
O3 P1 O1 105.52(12) . 4_565
O1 P1 O1 105.02(17) . 4_565
C1 O1 P1 121.8(2) . .
C2 C1 C6 123.4(3) . .
C2 C1 O1 119.1(3) . .
C6 C1 O1 117.3(3) . .
C1 C2 C3 115.5(3) . .
C1 C2 C8 123.5(3) . .
C3 C2 C8 121.0(3) . .
C4 C3 C2 123.1(4) . .
C5 C4 C3 118.6(3) . .
C5 C4 C12 120.7(3) . .
C3 C4 C12 120.8(4) . .
C4 C5 C6 121.2(3) . .
C5 C6 C1 117.9(3) . .
C5 C6 C7 120.1(3) . .
C1 C6 C7 122.0(3) . .
C6 C7 C6 116.5(4) 4_565 .
C11 C8 C9 107.2(3) . .
C11 C8 C10 110.2(4) . .
C9 C8 C10 105.7(3) . .
C11 C8 C2 111.4(3) . .
C9 C8 C2 112.0(3) . .
C10 C8 C2 110.1(3) . .
C14 N2 C13 122.5(5) . .
C14 N3 C15 111.2(5) . .
C15 N4 C16 107.0(5) . .
C16 N5 C17 103.5(5) . .
N1 C13 C17 126.9(5) . .
N1 C13 N2 118.9(5) . .
C17 C13 N2 114.2(5) . .
N3 C14 N2 127.0(6) . .
N4 C15 N3 128.4(5) . .
N4 C15 C17 105.1(5) . .
N3 C15 C17 126.5(5) . .
N5 C16 N4 113.4(6) . .
N5 C17 C13 130.3(5) . .
N5 C17 C15 111.1(5) . .
C13 C17 C15 118.6(5) . .
O6 P2 O5 119.1(2) . .
O6 P2 O4 105.23(13) . 4_565
O5 P2 O4 109.57(12) . 4_565
O6 P2 O4 105.23(13) . .
O5 P2 O4 109.57(12) . .
O4 P2 O4 107.50(19) 4_565 .
C18 O4 P2 123.0(2) . .
C23 C18 C19 121.9(4) . .
C23 C18 O4 116.6(3) . .
C19 C18 O4 121.3(4) . .
C20 C19 C18 115.9(4) . .
C20 C19 C25 119.7(4) . .
C18 C19 C25 124.3(4) . .
C19 C20 C21 124.4(4) . .
C22 C21 C20 117.2(4) . .
C22 C21 C29 122.0(5) . .
C20 C21 C29 120.8(4) . .
C23 C22 C21 121.8(4) . .
C22 C23 C18 118.7(4) . .
C22 C23 C24 119.7(4) . .
C18 C23 C24 121.5(4) . .
C23 C24 C23 112.2(4) . 4_565
C28 C25 C26 114.1(6) . .
C28 C25 C27 107.8(6) . .
C26 C25 C27 101.8(4) . .
C28 C25 C19 111.8(4) . .
C26 C25 C19 109.3(4) . .
C27 C25 C19 111.6(5) . .
C31 N7 C30 125.8(5) . .
C31 N8 C32 110.4(6) . .
C32 N9 C33 108.3(5) . .
C33 N10 C34 100.0(5) . .
N6 C30 C34 126.4(7) . .
N6 C30 N7 121.5(6) . .
C34 C30 N7 112.1(6) . .
N7 C31 N8 124.3(7) . .
N9 C32 N8 127.5(5) . .
N9 C32 C34 101.5(6) . .
N8 C32 C34 130.9(6) . .
N10 C33 N9 115.3(6) . .
N10 C33 C34 40.0(3) . .
N9 C33 C34 75.3(4) . .
C30 C34 N10 128.6(7) . .
C30 C34 C32 116.5(7) . .
N10 C34 C32 114.9(6) . .
C30 C34 C33 168.6(6) . .
N10 C34 C33 40.0(3) . .
C32 C34 C33 74.9(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 O2 1.476(3) .
P1 O3 1.481(3) .
P1 O1 1.589(2) .
P1 O1 1.589(2) 4_565
O1 C1 1.401(4) .
C1 C2 1.391(5) .
C1 C6 1.391(4) .
C2 C3 1.395(5) .
C2 C8 1.546(5) .
C3 C4 1.385(5) .
C4 C5 1.381(5) .
C4 C12 1.514(5) .
C5 C6 1.387(5) .
C6 C7 1.512(4) .
C7 C6 1.512(4) 4_565
C8 C11 1.528(5) .
C8 C9 1.529(5) .
C8 C10 1.534(6) .
N1 C13 1.296(6) .
N2 C14 1.329(7) .
N2 C13 1.395(7) .
N3 C14 1.301(7) .
N3 C15 1.367(7) .
N4 C15 1.314(7) .
N4 C16 1.361(7) .
N5 C16 1.297(7) .
N5 C17 1.346(7) .
C13 C17 1.365(7) .
C15 C17 1.395(7) .
P2 O6 1.482(4) .
P2 O5 1.485(3) .
P2 O4 1.588(3) 4_565
P2 O4 1.588(3) .
O4 C18 1.405(4) .
C18 C23 1.389(5) .
C18 C19 1.398(5) .
C19 C20 1.374(6) .
C19 C25 1.552(6) .
C20 C21 1.383(6) .
C21 C22 1.376(5) .
C21 C29 1.514(6) .
C22 C23 1.376(5) .
C23 C24 1.514(4) .
C24 C23 1.514(4) 4_565
C25 C28 1.488(8) .
C25 C26 1.506(7) .
C25 C27 1.535(7) .
N6 C30 1.303(7) .
N7 C31 1.311(8) .
N7 C30 1.473(8) .
N8 C31 1.318(7) .
N8 C32 1.338(8) .
N9 C32 1.318(8) .
N9 C33 1.352(8) .
N10 C33 1.328(7) .
N10 C34 1.329(8) .
C30 C34 1.331(8) .
C32 C34 1.440(8) .
C33 C34 2.035(10) .
O7 C35 1.427(11) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 HN1A O5 1.11(4) 1.72(5) 2.817(6) 170(3) 1_655
N1 HN1B N8 0.69(5) 3.04(5) 3.358(7) 111(5) 1_655
N2 HN2 O6 0.92(4) 1.70(5) 2.594(6) 165(4) 1_655
N4 HN4 O2 0.84(4) 1.86(5) 2.698(6) 176(5) .
N6 HN6B O2 0.71(5) 2.14(5) 2.849(7) 172(5) 1_454
N6 HN6A N3 0.75(4) 2.73(5) 3.258(7) 129(5) 1_454
N7 HN7 O3 0.80(5) 1.81(5) 2.611(6) 178(5) 1_454
N9 HN9 O5 0.84(4) 1.81(4) 2.643(6) 171(4) .
O3 H3 O7 0.82 2.03 2.691(8) 137.5 .
