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_1556913
_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         'C20 H19 N3 O'
_chemical_formula_sum            'C20 H19 N3 O'
_chemical_formula_weight         317.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-06-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-30 deposited with the CCDC.	2019-12-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.5974(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.10659(11)
_cell_length_b                   5.94958(5)
_cell_length_c                   13.62038(10)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.3540
_cell_measurement_theta_min      3.2700
_cell_volume                     807.530(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53a (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      150.00(10)
_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 0.999
_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 2.00 -- -41.82 -37.00-180.00 99 2 \w -129.00 -34.00 1.00 2.00 -- -41.82 178.00 90.00 95 3 \w -116.00 -17.00 1.00 2.00 -- -41.82 -37.00 -90.00 99 4 \w 57.00 131.00 1.00 2.00 -- 41.82 178.00-150.00 74 5 \w 17.00 116.00 1.00 2.00 -- 41.82 37.00 90.00 99 6 \w 24.00 110.00 1.00 8.00 -- 107.00 -94.00 150.00 86 7 \w 34.00 118.00 1.00 8.00 -- 107.00-125.00 150.00 84 8 \w 78.00 178.00 1.00 8.00 -- 107.00 61.00 -90.00 100 9 \w 24.00 110.00 1.00 8.00 -- 107.00 -94.00 -60.00 86 10 \w 74.00 178.00 1.00 8.00 -- 107.00 77.00-120.00 104 11 \w 94.00 178.00 1.00 8.00 -- 107.00 125.00 -60.00 84 12 \w 94.00 178.00 1.00 8.00 -- 107.00 125.00 150.00 84 13 \w 74.00 178.00 1.00 8.00 -- 107.00 77.00-150.00 104 14 \w 78.00 178.00 1.00 8.00 -- 107.00 61.00 -60.00 100 15 \w 94.00 178.00 1.00 8.00 -- 107.00 125.00 30.00 84 16 \w 81.00 178.00 1.00 8.00 -- 107.00 45.00 0.00 97 17 \w 35.00 136.00 1.00 8.00 -- 107.00 -61.00 0.00 101 18 \w 34.00 118.00 1.00 8.00 -- 107.00-125.00 0.00 84 19 \w -114.00 -13.00 1.00 2.00 -- -41.82 -59.00 11.00 101 20 \w -118.00 -9.00 1.00 2.00 -- -41.82 -77.00 -60.00 109 21 \w -118.00 -9.00 1.00 2.00 -- -41.82 -77.00 150.00 109 22 \w 57.00 131.00 1.00 2.00 -- 41.82 178.00 60.00 74 23 \w 78.00 178.00 1.00 8.00 -- 107.00 61.00 -30.00 100 24 \w 78.00 178.00 1.00 8.00 -- 107.00 59.00 152.00 100 25 \w 74.00 178.00 1.00 8.00 -- 107.00 77.00 30.00 104 26 \w 74.00 178.00 1.00 8.00 -- 107.00 77.00 0.00 104 27 \w 81.00 178.00 1.00 8.00 -- 107.00 45.00 120.00 97 28 \w 74.00 178.00 1.00 8.00 -- 107.00 77.00 120.00 104 29 \w 78.00 178.00 1.00 8.00 -- 107.00 61.00-180.00 100 30 \w 34.00 118.00 1.00 8.00 -- 107.00-125.00 -90.00 84 31 \w 78.00 178.00 1.00 8.00 -- 107.00 61.00-150.00 100 32 \w 76.00 178.00 1.00 8.00 -- 107.00 69.00 87.85 102 33 \w 74.00 178.00 1.00 8.00 -- 107.00 77.00 60.00 104'
_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      0.0929279000
_diffrn_orient_matrix_UB_12      0.0254897000
_diffrn_orient_matrix_UB_13      -0.0781592000
_diffrn_orient_matrix_UB_21      0.0824052000
_diffrn_orient_matrix_UB_22      0.1786576000
_diffrn_orient_matrix_UB_23      0.0655727000
_diffrn_orient_matrix_UB_31      0.0919859000
_diffrn_orient_matrix_UB_32      -0.1856442000
_diffrn_orient_matrix_UB_33      0.0524339000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15974
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.522
_diffrn_reflns_theta_min         3.291
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.02824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.40.53a (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    1.305
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
;
 Flack x determined using 1364 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Flack x: 0.00(8)  Shelxl 2018
Hooft y: 0.04(8)  Olex2
Absolute configuration established by the structure determination of the compound containing a chiral reference molecule 
of known absolute configuration and confirmed by anomalous-dispersion effects with diffraction measurements on the crystal.
;
_refine_ls_abs_structure_Flack   0.00(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3240
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0274
_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^)+(0.0402P)^2^+0.0804P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0705
_reflns_Friedel_coverage         0.799
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                3150
_reflns_number_total             3240
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc04849a2.cif
_cod_data_source_block           sr1
_cod_depositor_comments
;Adding full bibliography for 1556907--1556915.cif.

 Adding full bibliography for 1556907--1556915.cif.
;
_cod_database_code               1556913
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H20 N2 O2'
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.881
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
The NH was located in a difference map but refined with thermal parameters 1.2 times the equivalent isotropic displacement 
parameter of the nitrogen atom to which it is attached
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16A)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C14(H14A,H14B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C22(H22), C9(H9), C4(H4), C5(H5), C6(H6), C18(H18), C20(H20),
 C19(H19), C21(H21)
;
_shelx_res_checksum              93256
_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 23.590
_oxdiff_exptl_absorpt_empirical_full_min 0.548