Synthesis and Rotational Dynamics of Diazamacrocycles Having Bridged 1,4-Naphthylene as Framed Molecular Rotors
Kurimoto, Taichi; Inagaki, Yusuke; Ohara, Kazuaki; Yamaguchi, Kentaro; Setaka, Wataru; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01613C

data_7158931
_publ_section_title
;
 Synthesis and Rotational Dynamics of Diazamacrocycles Having Bridged
 1,4-Naphthylene as Framed Molecular Rotors
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01613C
_journal_year                    2022
_chemical_compound_source        no
_chemical_formula_moiety         'C34 H54 N2'
_chemical_formula_sum            'C34 H54 N2'
_chemical_formula_weight         490.79
_chemical_melting_point          383.1(8)
_chemical_name_common            C12NNp
_chemical_name_systematic        C12Np
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-08-19 deposited with the CCDC.	2022-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.8990(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7668(3)
_cell_length_b                   18.0397(5)
_cell_length_c                   15.5823(5)
_cell_measurement_reflns_used    9944
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.50
_cell_measurement_theta_min      3.74
_cell_volume                     3019.54(15)
_computing_cell_refinement       'APEX3 v2019.1-0 (Bruker AXS)'
_computing_data_collection       'APEX3 v2019.1-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2020)'
_computing_publication_material  'WinGX (Farrugia, 2020)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'Sir-2019 (IUCr, 2019)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  'multilayered conforcal mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24260
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.508
_diffrn_reflns_theta_min         3.753
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.455
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.080
_exptl_crystal_description       prism
_exptl_crystal_F_000             1088
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0058(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         6066
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0500P)^2^+0.7915P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1062
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5852
_reflns_number_total             6066
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01613c2.cif
_cod_data_source_block           C12NNp
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '382.3-383.8 K' was changed
to '383.1(8)' -- the average value was taken and precision was
estimated.

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7158931
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.839
_shelx_estimated_absorpt_t_max   0.914
_shelx_res_checksum              48805