Efficient syntheses of macrocycles ranging from 22‒28 atoms through spontaneous dimerization to yield bis-hydrazones
Sharma, Vishal R.; Mehmood, Arshad; Janesko, Benjamin G.; Simanek, Eric E.; RSC Advances 10 (2020) 3217–3220; doi:10.1039/C9RA08056B

data_7239788
_publ_section_title
;
 Efficient syntheses of macrocycles ranging from 22--28 atoms through
 spontaneous dimerization to yield bis-hydrazones
;
_journal_issue                   6
_journal_name_full               'RSC Advances'
_journal_page_first              3217
_journal_page_last               3220
_journal_paper_doi               10.1039/C9RA08056B
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C22 H34 N16 O4, 2(C2 F3 O2), 2(H2 O)'
_chemical_formula_sum            'C26 H38 F6 N16 O10'
_chemical_formula_weight         848.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-09-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-03 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.1840(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5858(3)
_cell_length_b                   18.8852(6)
_cell_length_c                   10.9389(4)
_cell_measurement_reflns_used    5480
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.98
_cell_volume                     1792.03(10)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      99.96
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12645
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.293
_diffrn_reflns_theta_min         2.981
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6235
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0476 before and 0.0404 after correction. The Ratio of minimum to maximum transmission is 0.8361. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_description       Block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.382
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.152
_refine_diff_density_max         0.674
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0473
_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^)+(0.0471P)^2^+1.5900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1179
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3504
_reflns_number_total             4393
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra08056b2.cif
_cod_data_source_block           1x1
_cod_depositor_comments
'Adding full bibliography for 7239788--7239792.cif.'
_cod_database_code               7239788
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.979
_shelx_estimated_absorpt_t_min   0.948
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C4(H4A,H4B), C7(H7A,H7B), C9(H9A,H9B), C6(H6A,H6B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 N5(H5), C8(H8A)
;
_shelx_res_checksum              93985
_olex2_submission_special_instructions 'No special instructions were received'