#------------------------------------------------------------------------------
#$Date: 2024-12-06 18:18:40 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296349 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/28/1572834.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_1572834
loop_
_publ_author_name
'Izzotti, Anthony R.'
'Gleason, James L.'
_publ_section_title
;
 Driving tert-butyl axial: the surprising cyclopropyl effect.
;
_journal_issue                   44
_journal_name_full               'Chemical science'
_journal_page_first              18592
_journal_page_last               18600
_journal_paper_doi               10.1039/d4sc05470a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C22 H26 N2'
_chemical_formula_sum            'C22 H26 N2'
_chemical_formula_weight         318.45
_chemical_name_systematic        4,9-dibenzyl-4,9-diazadispiro[2.2.26.23]decane
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-06-10
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.17 svn.r577a77a9 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-08-01 deposited with the CCDC.	2024-10-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.3740(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.1970(5)
_cell_length_b                   5.7050(2)
_cell_length_c                   20.8080(6)
_cell_measurement_reflns_used    1498
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      72.660
_cell_measurement_theta_min      6.012
_cell_volume                     1802.45(10)
_computing_cell_refinement       'Bruker APEX3'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker APEX3'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker D8'
_diffrn_measurement_method       '/w and /f scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14634
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.660
_diffrn_reflns_theta_min         6.012
_exptl_absorpt_coefficient_mu    0.519
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker AXScale'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.346
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.063
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.026
_refine_ls_extinction_coef       0.0081(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0438
_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)+(0.0481P)²+0.8605P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1165
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1498
_reflns_number_total             1767
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc05470a3.cif
_cod_data_source_block           AI1178
_cod_depositor_comments
'Adding full bibliography for 1572833--1572835.cif.'
_cod_database_code               1572834
_shelx_shelxl_version_number     2019/3
_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   0.968
_shelx_estimated_absorpt_t_min   0.841
_olex2_refinement_description
;
1.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3AB), C4(H4A,H4AB), C11(H11A,H11B), C12(H12A,H12B)
1.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C7(H7), C10(H10), C9(H9)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
N1 N 0.32804(6) 0.22326(18) 0.47887(5) 0.0418(3) Uani 1 1 d . . . . .
C2 C 0.33378(8) 0.2258(2) 0.55017(6) 0.0423(3) Uani 1 1 d . . . . .
C3 C 0.23946(7) 0.1433(2) 0.43608(6) 0.0432(3) Uani 1 1 d . . . . .
H3A H 0.234070 -0.022411 0.444257 0.052 Uiso 1 1 calc R U . . .
H3AB H 0.232710 0.162378 0.388191 0.052 Uiso 1 1 calc R U . . .
C4 C 0.35262(8) 0.4499(2) 0.45704(7) 0.0483(4) Uani 1 1 d . . . . .
H4A H 0.407926 0.501750 0.490534 0.058 Uiso 1 1 calc R U . . .
H4AB H 0.308031 0.565324 0.455594 0.058 Uiso 1 1 calc R U . . .
C6 C 0.40680(9) 0.2520(3) 0.37102(8) 0.0554(4) Uani 1 1 d . . . . .
H6 H 0.429913 0.133007 0.402763 0.067 Uiso 1 1 calc R U . . .
C5 C 0.36208(8) 0.4364(2) 0.38749(7) 0.0456(3) Uani 1 1 d . . . . .
C8 C 0.38361(10) 0.4173(3) 0.26051(8) 0.0613(4) Uani 1 1 d . . . . .
H8 H 0.390771 0.410538 0.218100 0.074 Uiso 1 1 calc R U . . .
C7 C 0.41741(11) 0.2429(3) 0.30808(8) 0.0618(4) Uani 1 1 d . . . . .
H7 H 0.447588 0.118089 0.297763 0.074 Uiso 1 1 calc R U . . .
C10 C 0.32852(9) 0.6107(2) 0.33928(7) 0.0555(4) Uani 1 1 d . . . . .
H10 H 0.298359 0.735831 0.349441 0.067 Uiso 1 1 calc R U . . .
C11 C 0.42493(9) 0.2279(3) 0.60223(7) 0.0578(4) Uani 1 1 d . . . . .
H11A H 0.434446 0.313440 0.644495 0.069 Uiso 1 1 calc R U . . .
H11B H 0.473931 0.231722 0.585610 0.069 Uiso 1 1 calc R U . . .
C12 C 0.37070(9) 0.0073(3) 0.59062(7) 0.0555(4) Uani 1 1 d . . . . .
H12A H 0.347483 -0.039418 0.625821 0.067 Uiso 1 1 calc R U . . .
H12B H 0.386985 -0.121171 0.566911 0.067 Uiso 1 1 calc R U . . .
C9 C 0.33910(10) 0.6019(3) 0.27606(8) 0.0637(4) Uani 1 1 d . . . . .
H9 H 0.316175 0.720539 0.244167 0.076 Uiso 1 1 calc R U . . .
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'
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
C2 N1 C3 108.82(9) . . ?
C2 N1 C4 112.24(9) . . ?
C4 N1 C3 113.39(10) . . ?
N1 C2 C3 115.00(10) . 7_556 ?
N1 C2 C11 115.79(11) . . ?
N1 C2 C12 115.71(11) . . ?
C11 C2 C3 120.05(11) . 7_556 ?
C11 C2 C12 60.17(9) . . ?
C12 C2 C3 119.23(11) . 7_556 ?
N1 C3 C2 113.34(10) . 7_556 ?
N1 C3 H3A 108.9 . . ?
N1 C3 H3AB 108.9 . . ?
C2 C3 H3A 108.9 7_556 . ?
C2 C3 H3AB 108.9 7_556 . ?
H3A C3 H3AB 107.7 . . ?
N1 C4 H4A 109.1 . . ?
N1 C4 H4AB 109.1 . . ?
N1 C4 C5 112.35(10) . . ?
H4A C4 H4AB 107.9 . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4AB 109.1 . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C7 C6 C5 120.76(13) . . ?
C6 C5 C4 120.78(12) . . ?
C10 C5 C4 120.92(12) . . ?
C10 C5 C6 118.28(12) . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.59(14) . . ?
C9 C8 H8 120.2 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.39(14) . . ?
C8 C7 H7 119.8 . . ?
C5 C10 H10 119.5 . . ?
C5 C10 C9 121.04(13) . . ?
C9 C10 H10 119.5 . . ?
C2 C11 H11A 117.7 . . ?
C2 C11 H11B 117.7 . . ?
C2 C11 C12 60.23(8) . . ?
H11A C11 H11B 114.9 . . ?
C12 C11 H11A 117.7 . . ?
C12 C11 H11B 117.7 . . ?
C2 C12 H12A 117.8 . . ?
C2 C12 H12B 117.8 . . ?
C11 C12 C2 59.60(9) . . ?
C11 C12 H12A 117.8 . . ?
C11 C12 H12B 117.8 . . ?
H12A C12 H12B 114.9 . . ?
C8 C9 C10 119.92(14) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
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
N1 C2 1.4539(15) . ?
N1 C3 1.4730(15) . ?
N1 C4 1.4706(16) . ?
C2 C3 1.5109(16) 7_556 ?
C2 C11 1.4966(17) . ?
C2 C12 1.5063(18) . ?
C3 H3A 0.9700 . ?
C3 H3AB 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4AB 0.9700 . ?
C4 C5 1.5094(17) . ?
C6 H6 0.9300 . ?
C6 C5 1.3865(18) . ?
C6 C7 1.380(2) . ?
C5 C10 1.3821(19) . ?
C8 H8 0.9300 . ?
C8 C7 1.376(2) . ?
C8 C9 1.377(2) . ?
C7 H7 0.9300 . ?
C10 H10 0.9300 . ?
C10 C9 1.385(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.505(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C9 H9 0.9300 . ?
