#------------------------------------------------------------------------------
#$Date: 2021-09-06 11:03:40 +0200 (lun 06 de sep de 2021) $
#$Revision: 268512 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/85/7128505.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_7128505
loop_
_publ_author_name
'Altenhofer, Erich F.'
'Lawler, Michael J.'
'Kumar, Pankaj'
'Joyce, Leo A.'
'Fowler-Watters, Matthew'
'Pei, Tao'
'Li, Zhen'
_publ_section_title
;
 Synthesis of a novel cyclopropyl phosphonate nucleotide as a phosphate
 mimic.
;
_journal_issue                   55
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              6808
_journal_page_last               6811
_journal_paper_doi               10.1039/d1cc02328d
_journal_volume                  57
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H25 N2 O8 P'
_chemical_formula_sum            'C16 H25 N2 O8 P'
_chemical_formula_weight         404.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-06-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-12-03 deposited with the CCDC.	2021-06-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4700(4)
_cell_length_b                   23.4314(8)
_cell_length_c                   7.3958(3)
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      72.18
_cell_measurement_theta_min      3.77
_cell_volume                     1987.68(13)
_computing_cell_refinement       'Bruker Apex3 V.2018.1-0/SAINT V8.38A'
_computing_data_collection       'Bruker Apex3 V.2018.1-0'
_computing_data_reduction        'Bruker Apex3 V.2018.1-0/SAINT V8.38A'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multi-layer optics'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            45084
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.555
_diffrn_reflns_theta_min         3.773
_diffrn_source                   'Incoatec IMuS microfocus Cu tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.633
_exptl_absorpt_correction_T_max  0.3859
_exptl_absorpt_correction_T_min  0.2310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          1.2
_exptl_crystal_size_mid          1
_exptl_crystal_size_min          0.88
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Flack x determined using 1543 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.029(10)
_refine_ls_extinction_coef       0.022(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         3941
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0617
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0981P)²+0.7138P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1638
_refine_ls_wR_factor_ref         0.1661
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3806
_reflns_number_total             3941
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc02328d2.cif
_cod_data_source_block           s1
_cod_depositor_comments          'Adding full bibliography for 7128505.cif.'
_cod_database_code               7128505
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.328
_shelx_estimated_absorpt_t_min   0.245
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
 O5-H5
 0.93 with sigma of 0.02
 P1-O2 \\sim P1-O3
 with sigma of 0.02
 O2-C12 \\sim O3-C14
 with sigma of 0.02
3. Others
 Fixed Sof: C14(0.5) H14A(0.5) H14B(0.5) C14'(0.5) H14C(0.5) H14D(0.5)
 C15(0.5) H15A(0.5) H15B(0.5) H15C(0.5) C15'(0.5) H15D(0.5) H15E(0.5) H15F(0.5)
4.a Ternary CH refined with riding coordinates:
 C1(H1), C4(H4), C7(H7), C6(H6), C3(H3), C5(H5A)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C12(H12A,H12B), C14(H14A,H14B), C14'(H14C,H14D)
4.c Me refined with riding coordinates:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C15'(H15D,H15E,H15F)
4.d Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9)
4.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.58275(12) 0.87825(8) 0.8422(2) 0.0961(6) Uani 1 1 d D . . . .
O4 O 0.9111(2) 0.89658(11) 0.5618(3) 0.0508(6) Uani 1 1 d . . . . .
O8 O 1.2355(2) 0.91869(11) 0.5842(5) 0.0660(8) Uani 1 1 d . . . . .
O7 O 1.3084(3) 0.73005(13) 0.6643(5) 0.0710(8) Uani 1 1 d . . . . .
O6 O 1.0449(3) 0.92978(15) 0.1505(4) 0.0702(8) Uani 1 1 d . . . . .
O1 O 0.4993(3) 0.84834(17) 0.7237(6) 0.0872(11) Uani 1 1 d . . . . .
N2 N 1.2705(3) 0.82422(14) 0.6213(5) 0.0504(7) Uani 1 1 d . . . . .
N1 N 1.0914(2) 0.85546(12) 0.5123(4) 0.0455(7) Uani 1 1 d . . . . .
C11 C 1.2023(3) 0.86971(14) 0.5730(5) 0.0449(7) Uani 1 1 d . . . . .
C10 C 1.2387(3) 0.76688(16) 0.6206(6) 0.0519(8) Uani 1 1 d . . . . .
C8 C 1.0531(3) 0.79983(15) 0.5133(6) 0.0541(9) Uani 1 1 d . . . . .
H8 H 0.977599 0.792023 0.474719 0.065 Uiso 1 1 calc R . . . .
O5 O 0.8207(3) 0.96634(15) 0.1567(5) 0.0809(10) Uani 1 1 d D . . . .
C1 C 0.6680(3) 0.9273(2) 0.7215(8) 0.0770(15) Uani 1 1 d . . . . .
H1 H 0.721986 0.950637 0.792691 0.092 Uiso 1 1 calc R . . . .
C4 C 0.8237(3) 0.92948(15) 0.4690(6) 0.0525(8) Uani 1 1 d . . . . .
H4 H 0.835405 0.970093 0.494979 0.063 Uiso 1 1 calc R . . . .
C7 C 1.0127(3) 0.90007(14) 0.4539(4) 0.0451(7) Uani 1 1 d . . . . .
H7 H 1.049796 0.937284 0.472436 0.054 Uiso 1 1 calc R . . . .
C6 C 0.9700(3) 0.89577(18) 0.2585(5) 0.0539(8) Uani 1 1 d . . . . .
H6 H 0.970973 0.856017 0.217334 0.065 Uiso 1 1 calc R . . . .
C3 C 0.7068(3) 0.91160(16) 0.5358(6) 0.0555(9) Uani 1 1 d . . . . .
H3 H 0.679663 0.874388 0.492350 0.067 Uiso 1 1 calc R . . . .
C9 C 1.1203(3) 0.75673(16) 0.5676(7) 0.0607(10) Uani 1 1 d . . . . .
H9 H 1.090295 0.719876 0.571011 0.073 Uiso 1 1 calc R . . . .
C5 C 0.8437(4) 0.91861(17) 0.2665(6) 0.0583(9) Uani 1 1 d . . . . .
H5A H 0.791405 0.887754 0.228919 0.070 Uiso 1 1 calc R . . . .
C2 C 0.6148(4) 0.9551(2) 0.5603(13) 0.103(2) Uani 1 1 d . . . . .
H2A H 0.535575 0.944641 0.528865 0.123 Uiso 1 1 calc R . . . .
H2B H 0.635007 0.994581 0.536488 0.123 Uiso 1 1 calc R . . . .
O3 O 0.6677(5) 0.8398(3) 0.9540(9) 0.143(2) Uani 1 1 d D . . . .
O2 O 0.5277(5) 0.9137(4) 0.9975(10) 0.210(5) Uani 1 1 d D . . . .
C16 C 1.0388(8) 0.9155(3) -0.0382(7) 0.110(2) Uani 1 1 d . . . . .
H16A H 1.093287 0.938436 -0.104502 0.165 Uiso 1 1 calc GR . . . .
H16B H 0.961317 0.922537 -0.082062 0.165 Uiso 1 1 calc GR . . . .
H16C H 1.057544 0.875855 -0.054038 0.165 Uiso 1 1 calc GR . . . .
C12 C 0.4177(13) 0.9211(7) 1.047(2) 0.232(8) Uani 1 1 d D . . . .
H12A H 0.409402 0.961862 1.066347 0.279 Uiso 1 1 calc R . . . .
H12B H 0.372002 0.912482 0.939757 0.279 Uiso 1 1 calc R . . . .
C13 C 0.3695(16) 0.9003(11) 1.162(2) 0.283(11) Uani 1 1 d . . . . .
H13A H 0.290582 0.913980 1.165000 0.425 Uiso 1 1 calc R . . . .
H13B H 0.369524 0.859690 1.146126 0.425 Uiso 1 1 calc R . . . .
H13C H 0.407376 0.909666 1.274245 0.425 Uiso 1 1 calc R . . . .
C14 C 0.695(3) 0.7869(9) 0.908(4) 0.144(11) Uani 0.5 1 d D . P A 1
H14A H 0.660825 0.784253 0.788471 0.173 Uiso 0.5 1 calc R . P A 1
H14B H 0.643251 0.765050 0.984998 0.173 Uiso 0.5 1 calc R . P A 1
C14' C 0.760(5) 0.8001(13) 0.863(4) 0.25(3) Uani 0.5 1 d . . P A 2
H14C H 0.833308 0.796019 0.928349 0.296 Uiso 0.5 1 calc R . P A 2
H14D H 0.771663 0.805622 0.734556 0.296 Uiso 0.5 1 calc R . P A 2
C15 C 0.795(4) 0.748(2) 0.891(5) 0.25(2) Uani 0.5 1 d . . P A 1
H15A H 0.767821 0.711513 0.849712 0.382 Uiso 0.5 1 calc R . P A 1
H15B H 0.849450 0.763390 0.806234 0.382 Uiso 0.5 1 calc R . P A 1
H15C H 0.831500 0.743776 1.006968 0.382 Uiso 0.5 1 calc R . P A 1
C15' C 0.659(3) 0.7553(13) 0.919(3) 0.165(10) Uani 0.5 1 d . . P A 2
H15D H 0.681259 0.717483 0.882753 0.247 Uiso 0.5 1 calc R . P A 2
H15E H 0.647322 0.756235 1.047336 0.247 Uiso 0.5 1 calc R . P A 2
H15F H 0.587445 0.765562 0.859097 0.247 Uiso 0.5 1 calc R . P A 2
H2 H 1.358(10) 0.829(4) 0.633(18) 0.198 Uiso 1 1 d R . . . .
H5 H 0.886(8) 0.987(5) 0.203(18) 0.247 Uiso 1 1 d DR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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
_geom_angle_publ_flag
O1 P1 C1 111.8(3) . . ?
O1 P1 O3 116.4(3) . . ?
O1 P1 O2 115.5(3) . . ?
O3 P1 C1 107.4(3) . . ?
O2 P1 C1 104.7(4) . . ?
O2 P1 O3 99.8(5) . . ?
C7 O4 C4 105.9(3) . . ?
C6 O6 C16 112.7(4) . . ?
C11 N2 C10 126.9(3) . . ?
C11 N1 C7 119.6(3) . . ?
C8 N1 C11 121.2(3) . . ?
C8 N1 C7 119.1(3) . . ?
O8 C11 N2 122.7(3) . . ?
O8 C11 N1 122.5(3) . . ?
N2 C11 N1 114.8(3) . . ?
O7 C10 N2 120.7(3) . . ?
O7 C10 C9 125.2(4) . . ?
N2 C10 C9 114.2(3) . . ?
C9 C8 N1 122.3(3) . . ?
C3 C1 P1 118.3(3) . . ?
C2 C1 P1 117.8(3) . . ?
C2 C1 C3 59.5(4) . . ?
O4 C4 C3 108.6(3) . . ?
O4 C4 C5 105.8(3) . . ?
C3 C4 C5 114.3(3) . . ?
O4 C7 N1 107.7(3) . . ?
O4 C7 C6 105.4(3) . . ?
N1 C7 C6 115.8(3) . . ?
O6 C6 C7 107.5(3) . . ?
O6 C6 C5 113.3(3) . . ?
C7 C6 C5 103.9(3) . . ?
C1 C3 C4 120.4(3) . . ?
C2 C3 C1 60.2(4) . . ?
C2 C3 C4 119.3(4) . . ?
C8 C9 C10 120.3(3) . . ?
O5 C5 C4 113.8(3) . . ?
O5 C5 C6 115.4(4) . . ?
C4 C5 C6 103.6(3) . . ?
C3 C2 C1 60.3(3) . . ?
P1 O3 C14' 122.7(15) . . ?
C14 O3 P1 123.5(9) . . ?
C12 O2 P1 131.4(8) . . ?
C13 C12 O2 128(2) . . ?
O3 C14 C15 142(4) . . ?
O3 C14' C15' 78(3) . . ?
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 O1 1.475(4) . ?
P1 C1 1.753(6) . ?
P1 O3 1.563(7) . ?
P1 O2 1.552(6) . ?
O4 C4 1.439(4) . ?
O4 C7 1.415(4) . ?
O8 C11 1.212(4) . ?
O7 C10 1.220(5) . ?
O6 C6 1.418(5) . ?
O6 C16 1.437(6) . ?
N2 C11 1.369(5) . ?
N2 C10 1.392(5) . ?
N1 C11 1.390(4) . ?
N1 C8 1.375(5) . ?
N1 C7 1.447(4) . ?
C10 C9 1.433(5) . ?
C8 C9 1.333(6) . ?
O5 C5 1.407(5) . ?
C1 C3 1.489(7) . ?
C1 C2 1.489(10) . ?
C4 C3 1.489(5) . ?
C4 C5 1.536(6) . ?
C7 C6 1.529(5) . ?
C6 C5 1.545(6) . ?
C3 C2 1.478(5) . ?
O3 C14 1.322(19) . ?
O3 C14' 1.56(5) . ?
O2 C12 1.325(13) . ?
C12 C13 1.129(19) . ?
C14 C15 1.46(4) . ?
C14' C15' 1.62(4) . ?
