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_7239790
_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         'C2 F3 O2, C12 H19 N8 O2, 2(H2 O)'
_chemical_formula_sum            'C14 H23 F3 N8 O6'
_chemical_formula_weight         456.40
_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   mixed
_audit_creation_date             2019-02-24
_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                 100.156(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.754(3)
_cell_length_b                   13.7241(16)
_cell_length_c                   15.904(2)
_cell_measurement_reflns_used    9047
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.823
_cell_measurement_theta_min      2.969
_cell_volume                     4673.8(10)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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      100.02
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0466
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
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_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            49604
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        20.868
_diffrn_reflns_theta_max         20.868
_diffrn_reflns_theta_min         2.940
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.7446
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_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0777 before and 0.0718 after correction. The Ratio of minimum to maximum transmission is 0.9132. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       Block
_exptl_crystal_F_000             1904
_exptl_crystal_size_max          0.462
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.222
_refine_diff_density_max         0.936
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         2444
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0987
_refine_ls_R_factor_gt           0.0841
_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^)+(0.1297P)^2^+46.0410P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2230
_refine_ls_wR_factor_ref         0.2405
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2035
_reflns_number_total             2444
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra08056b2.cif
_cod_data_source_block           2x2
_cod_depositor_comments
'Adding full bibliography for 7239788--7239792.cif.'
_cod_original_cell_volume        4673.7(10)
_cod_database_code               7239790
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.975
_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
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O5(H5C,H5D), O6(H6C,H6D)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,
 H10B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N5(H5), N7(H7), N8(H8), C8(H8A)
;
_shelx_res_checksum              54672
_shelx_fab_checksum              87540
_olex2_submission_special_instructions 'No special instructions were received'