Readily accessible sp<sup>3</sup>-rich cyclic hydrazine frameworks exploiting nitrogen fluxionality.
Dean, Conor; Rajkumar, Sundaram; Roesner, Stefan; Carson, Nessa; Clarkson, Guy J.; Wills, Martin; Jones, Matthew; Shipman, Michael; Chemical science 11 (2020) 1636–1642; doi:10.1039/c9sc04849a

data_1556911
_publ_section_title
;
 Readily accessible sp<sup>3</sup>-rich cyclic hydrazine frameworks
 exploiting nitrogen fluxionality.
;
_journal_issue                   6
_journal_name_full               'Chemical science'
_journal_page_first              1636
_journal_page_last               1642
_journal_paper_doi               10.1039/c9sc04849a
_journal_volume                  11
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H21 F3 N2 O4 S'
_chemical_formula_sum            'C24 H21 F3 N2 O4 S'
_chemical_formula_weight         490.49
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-04
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-07-30 deposited with the CCDC.	2019-12-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   32.8358(3)
_cell_length_b                   11.60538(10)
_cell_length_c                   5.85758(7)
_cell_measurement_reflns_used    42722
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.2910
_cell_measurement_theta_min      3.9570
_cell_volume                     2232.16(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -64.00  31.00   1.00    3.00    --  -41.61  37.00  30.00   95
  2  \w   -127.00 -34.00   1.00    3.00    --  -41.61 178.00  90.00   93
  3  \w   -112.00 -15.00   1.00    3.00    --  -41.61 -57.00  60.00   97
  4  \w   -115.00 -19.00   1.00    3.00    --  -41.61 -37.00-150.00   96
  5  \w     25.00 109.00   1.00   12.00    --  106.00 -94.00  60.00   84
  6  \w     82.00 178.00   1.00   12.00    --  106.00  30.00   0.00   96
  7  \w     82.00 177.00   1.00   12.00    --  106.00  45.00-180.00   95
  8  \w     78.00 176.00   1.00   12.00    --  106.00  61.00  90.00   98
  9  \w     34.00 121.00   1.00   12.00    --  106.00-125.00 -30.00   87
 10  \w     31.00 116.00   1.00   12.00    --  106.00-112.00-148.00   85
 11  \w     34.00 121.00   1.00   12.00    --  106.00-125.00   0.00   87
 12  \w     75.00 178.00   1.00   12.00    --  106.00  77.00-120.00  103
 13  \w     82.00 177.00   1.00   12.00    --  106.00  45.00  30.00   95
 14  \w     32.00 137.00   1.00   12.00    --  106.00 -77.00 120.00  105
 15  \w     35.00 130.00   1.00   12.00    --  106.00 -45.00 150.00   95
 16  \w     32.00 137.00   1.00   12.00    --  106.00 -77.00 -30.00  105
 17  \w   -112.00 -15.00   1.00    3.00    --  -41.61 -57.00 -30.00   97
 18  \w   -112.00 -15.00   1.00    3.00    --  -41.61 -57.00 150.00   97
 19  \w   -115.00 -10.00   1.00    3.00    --  -41.61 -77.00 -90.00  105
 20  \w    -68.00  29.00   1.00    3.00    --  -41.61  57.00 120.00   97
 21  \w     75.00 178.00   1.00   12.00    --  106.00  77.00-150.00  103
 22  \w     78.00 176.00   1.00   12.00    --  106.00  61.00-150.00   98
 23  \w     75.00 178.00   1.00   12.00    --  106.00  77.00 120.00  103
 24  \w     75.00 178.00   1.00   12.00    --  106.00  77.00 -60.00  103
 25  \w     82.00 177.00   1.00   12.00    --  106.00  45.00 -60.00   95
 26  \w     78.00 176.00   1.00   12.00    --  106.00  61.00  30.00   98
 27  \w     75.00 178.00   1.00   12.00    --  106.00  77.00 -30.00  103
 28  \w     78.00 176.00   1.00   12.00    --  106.00  61.00-180.00   98
 29  \w     78.00 176.00   1.00   12.00    --  106.00  61.00 120.00   98
 30  \w     78.00 176.00   1.00   12.00    --  106.00  61.00 150.00   98
 31  \w     75.00 178.00   1.00   12.00    --  106.00  77.00 -90.00  103
 32  \w     78.00 176.00   1.00   12.00    --  106.00  61.00  60.00   98
 33  \w   -112.00 -62.00   1.00    3.00    --  -41.61-143.00 140.00   50
 34  \w   -115.00 -10.00   1.00    3.00    --  -41.61 -77.00  60.00  105
 35  \w   -115.00 -10.00   1.00    3.00    --  -41.61 -77.00   0.00  105
 36  \w   -115.00 -10.00   1.00    3.00    --  -41.61 -77.00-180.00  105
 37  \w     75.00 178.00   1.00   12.00    --  106.00  77.00  90.00  103
 38  \w     75.00 178.00   1.00   12.00    --  106.00  77.00-180.00  103
 39  \w     78.00 176.00   1.00   12.00    --  106.00  61.00   0.00   98
 40  \w     78.00 176.00   1.00   12.00    --  106.00  61.00 -90.00   98
 41  \w     75.00 178.00   1.00   12.00    --  106.00  77.00  30.00  103
 42  \w     78.00 176.00   1.00   12.00    --  106.00  61.00 -60.00   98
 43  \w     78.00 176.00   1.00   12.00    --  106.00  61.00-120.00   98
 44  \w     35.00 130.00   1.00   12.00    --  106.00 -45.00 -30.00   95
 45  \w     78.00 176.00   1.00   12.00    --  106.00  61.00 -30.00   98
 46  \w     35.00 122.00   1.00   12.00    --  106.00-127.00 -49.00   87
 47  \w     75.00 178.00   1.00   12.00    --  106.00  77.00   0.00  103
 48  \w     75.00 178.00   1.00   12.00    --  106.00  77.00  60.00  103
 49  \w   -115.00 -10.00   1.00    3.00    --  -41.61 -77.00 150.00  105
 50  \w   -115.00 -19.00   1.00    3.00    --  -41.61 -37.00   0.00   96
 51  \w   -115.00 -10.00   1.00    3.00    --  -41.61 -77.00-150.00  105
 52  \w     57.00 128.00   1.00    3.00    --   41.61 178.00 -30.00   71
 53  \w     75.00 169.00   1.00   12.00    --  106.00  77.00 150.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0458786000
_diffrn_orient_matrix_UB_12      -0.0277282000
_diffrn_orient_matrix_UB_13      0.0031571000
_diffrn_orient_matrix_UB_21      0.0094991000
_diffrn_orient_matrix_UB_22      -0.1272232000
_diffrn_orient_matrix_UB_23      -0.0528252000
_diffrn_orient_matrix_UB_31      0.0025203000
_diffrn_orient_matrix_UB_32      -0.0257326000
_diffrn_orient_matrix_UB_33      0.2576446000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0917
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            72297
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.525
_diffrn_reflns_theta_min         4.040
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.827
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.096
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
;
 Flack x determined using 1810 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).

Flack x: 0.015(9) Shelx2018
Hooft y: 0.009(5) Olex2
;
_refine_ls_abs_structure_Flack   0.015(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0616
_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^)+(0.0243P)^2^+7.3814P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1477
_refine_ls_wR_factor_ref         0.1478
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                4477
_reflns_number_total             4499
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc04849a2.cif
_cod_data_source_block           cd5
_cod_depositor_comments
;Adding full bibliography for 1556907--1556915.cif.

 Adding full bibliography for 1556907--1556915.cif.
;
_cod_database_code               1556911
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H20 N2 O3 S F3'
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.610
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C26(H26), C14(H14), C18(H18), C17(H17), C15(H15), C5(H5), C23(H23),
 C25(H25), C1(H1), C4(H4), C2(H2), C3(H3)
2.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_shelx_res_checksum              30667
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.144
_oxdiff_exptl_absorpt_empirical_full_min 0.372