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_1556914
_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 rmad
_chemical_formula_moiety         'C28 H30 N2 O2'
_chemical_formula_sum            'C28 H30 N2 O2'
_chemical_formula_weight         426.54
_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             2019-08-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-23 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                   8.33247(2)
_cell_length_b                   15.71709(6)
_cell_length_c                   17.93381(5)
_cell_measurement_reflns_used    54333
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.5390
_cell_measurement_theta_min      2.7790
_cell_volume                     2348.651(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_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 0.997
_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   -116.00 -17.00   1.00    1.00    --  -41.82 -37.00 -30.00   99
  2  \w    -66.00  33.00   1.00    1.00    --  -41.82  37.00 150.00   99
  3  \w    -74.00  34.00   1.00    1.00    --  -41.82  77.00-120.00  108
  4  \w      8.00  34.00   1.00    1.00    --   41.82  83.00 -29.61   26
  5  \w     81.00 178.00   1.00    4.00    --  107.00  45.00-180.00   97
  6  \w     78.00 178.00   1.00    4.00    --  107.00  61.00 120.00  100
  7  \w     35.00 136.00   1.00    4.00    --  107.00 -61.00-180.00  101
  8  \w     34.00 112.00   1.00    4.00    --  107.00-125.00 120.00   78
  9  \w     81.00 178.00   1.00    4.00    --  107.00  45.00 -90.00   97
 10  \w     97.00 178.00   1.00    4.00    --  107.00 125.00-150.00   81
 11  \w     24.00 107.00   1.00    4.00    --  107.00 -94.00 -30.00   83
 12  \w     24.00 107.00   1.00    4.00    --  107.00 -94.00 120.00   83
 13  \w     78.00 178.00   1.00    4.00    --  107.00  61.00   0.00  100
 14  \w     35.00 136.00   1.00    4.00    --  107.00 -61.00  60.00  101
 15  \w     34.00 115.00   1.00    4.00    --  107.00-128.00-102.00   81
 16  \w     97.00 178.00   1.00    4.00    --  107.00 125.00-180.00   81
 17  \w     35.00 125.00   1.00    4.00    --  107.00-141.00  85.00   90
 18  \w     37.00 127.00   1.00    4.00    --  107.00-144.00   9.58   90
 19  \w   -114.00 -14.00   1.00    1.00    --  -41.82 -57.00 120.00  100
 20  \w      8.00  42.00   1.00    1.00    --   41.82  81.00 -77.48   34
 21  \w      8.00  42.00   1.00    1.00    --   41.82  81.00 171.92   34
 22  \w      7.00  33.00   1.00    1.00    --   41.82  84.00 109.34   26
 23  \w      8.00  42.00   1.00    1.00    --   41.82  81.00-117.99   34
 24  \w     78.00 178.00   1.00    4.00    --  107.00  61.00 -60.00  100
 25  \w     78.00 178.00   1.00    4.00    --  107.00  60.00 144.03  100
 26  \w     78.00 178.00   1.00    4.00    --  107.00  61.00  60.00  100
 27  \w     78.00 178.00   1.00    4.00    --  107.00  61.00  90.00  100
 28  \w     97.00 178.00   1.00    4.00    --  107.00 125.00 120.00   81
 29  \w     78.00 178.00   1.00    4.00    --  107.00  61.00 -30.00  100
 30  \w     78.00 178.00   1.00    4.00    --  107.00  61.00-120.00  100
 31  \w     78.00 178.00   1.00    4.00    --  107.00  61.00 -90.00  100
 32  \w     78.00 178.00   1.00    4.00    --  107.00  61.00-180.00  100
 33  \w     78.00 178.00   1.00    4.00    --  107.00  61.00 107.82  100
 34  \w     78.00 178.00   1.00    4.00    --  107.00  61.00  30.00  100
 35  \w     78.00 178.00   1.00    4.00    --  107.00  62.00  74.48  100
 36  \w     75.00 178.00   1.00    4.00    --  107.00  74.00-152.84  103
 37  \w     76.00 178.00   1.00    4.00    --  107.00  72.00  33.79  102
 38  \w     78.00 178.00   1.00    4.00    --  107.00  61.00-150.00  100
 39  \w    -66.00  33.00   1.00    1.00    --  -41.82  37.00  60.00   99
 40  \w   -114.00 -14.00   1.00    1.00    --  -41.82 -57.00-120.00  100
 41  \w      8.00  42.00   1.00    1.00    --   41.82  81.00  13.45   34
 42  \w      8.00  34.00   1.00    1.00    --   41.82  83.00  78.36   26
 43  \w      7.00  33.00   1.00    1.00    --   41.82  84.00 126.66   26
 44  \w     79.00 178.00   1.00    4.00    --  107.00  56.00 -32.60   99
 45  \w     81.00 178.00   1.00    4.00    --  107.00  45.00 -60.00   97
 46  \w     78.00 178.00   1.00    4.00    --  107.00  59.00-155.30  100
 47  \w     29.00 108.00   1.00    4.00    --  107.00-106.00 176.81   79
 48  \w     77.00 178.00   1.00    4.00    --  107.00  67.00 -12.31  101
 49  \w     78.00 178.00   1.00    4.00    --  107.00  63.00 158.14  100
 50  \w     78.00 178.00   1.00    4.00    --  107.00  61.00 150.00  100
 51  \w     34.00 112.00   1.00    4.00    --  107.00-125.00 -60.00   78
 52  \w     76.00 178.00   1.00    4.00    --  107.00  72.00  87.25  102
 53  \w     81.00 130.00   1.00    4.00    --  107.00  45.00 -30.00   49
 54  \w     81.00 178.00   1.00    4.00    --  107.00  45.00  30.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1682378000
_diffrn_orient_matrix_UB_12      -0.0009115000
_diffrn_orient_matrix_UB_13      0.0356225000
_diffrn_orient_matrix_UB_21      0.0764893000
_diffrn_orient_matrix_UB_22      -0.0053588000
_diffrn_orient_matrix_UB_23      -0.0780653000
_diffrn_orient_matrix_UB_31      0.0057363000
_diffrn_orient_matrix_UB_32      0.0978653000
_diffrn_orient_matrix_UB_33      -0.0039339000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0106
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            70707
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.664
_diffrn_reflns_theta_min         3.740
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
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    1.206
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 2014 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 Flack x: 0.01(3) Shelx 2018
 Hooft y: 0.02(3) Olex2
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4736
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0277
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0385P)^2^+0.3008P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0703
_refine_ls_wR_factor_ref         0.0705
_reflns_Friedel_coverage         0.754
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                4709
_reflns_number_total             4736
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc04849a2.cif
_cod_data_source_block           sr5
_cod_depositor_comments
;Adding full bibliography for 1556907--1556915.cif.

 Adding full bibliography for 1556907--1556915.cif.
;
_cod_original_cell_volume        2348.651(13)
_cod_database_code               1556914
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H20 N2 O2'
_shelx_estimated_absorpt_t_max   0.890
_shelx_estimated_absorpt_t_min   0.890
_reflns_odcompleteness_completeness 99.85
_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:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C18(H18), C19(H19), C21(H21), C22(H22),
 C23(H23), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              8298
_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 2.335
_oxdiff_exptl_absorpt_empirical_full_min 0.738