Synthesis of a novel cyclopropyl phosphonate nucleotide as a phosphate mimic.
Altenhofer, Erich F.; Lawler, Michael J.; Kumar, Pankaj; Joyce, Leo A.; Fowler-Watters, Matthew; Pei, Tao; Li, Zhen; Chemical communications (Cambridge, England) 57 (2021) 6808–6811; doi:10.1039/d1cc02328d

data_7128505
_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       '\f and \w 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+0.001xFc^2^\l^3^/sin(2\q)]^-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/[\s^2^(Fo^2^)+(0.0981P)^2^+0.7138P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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_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)
;
_shelx_res_checksum              18503
_olex2_submission_special_instructions 'No special instructions were received'