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_7239792
_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
'C28 H46 N16 O4, 2(C2 F3 O2), 2(C H4 O), H2 O'
_chemical_formula_sum            'C34 H56 F6 N16 O11'
_chemical_formula_weight         978.94
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-09-29
_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                102.8940(10)
_cell_angle_beta                 95.7540(10)
_cell_angle_gamma                103.8890(10)
_cell_formula_units_Z            2
_cell_length_a                   10.0220(3)
_cell_length_b                   13.0296(4)
_cell_length_c                   18.2777(5)
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.08
_cell_measurement_theta_min      2.88
_cell_volume                     2228.51(11)
_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      100.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0312
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            84991
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.128
_diffrn_reflns_theta_min         2.876
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0497 before and 0.0474 after correction. The Ratio of minimum to maximum transmission is 0.9611. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_description       Block
_exptl_crystal_F_000             1028
_refine_diff_density_max         1.649
_refine_diff_density_min         -1.410
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     614
_refine_ls_number_reflns         9843
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0793
_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^)+(0.1153P)^2^+5.5261P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2154
_refine_ls_wR_factor_ref         0.2318
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8016
_reflns_number_total             9843
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra08056b2.cif
_cod_data_source_block           6x6
_cod_depositor_comments
'Adding full bibliography for 7239788--7239792.cif.'
_cod_original_cell_volume        2228.50(11)
_cod_database_code               7239792
_shelx_shelxl_version_number     2018/3
_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 C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O11(H11C,H11D)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C11(H11A,H11B), C13(H13A,H13B), C2(H2A,H2B), C28(H28A,H28B),
 C18(H18A,H18B), C1(H1A,H1B), C25(H25A,H25B), C23(H23A,H23B), C9(H9A,H9B),
 C27(H27A,H27B), C10(H10A,H10B), C4(H4A,H4B), C21(H21A,H21B), C3(H3A,H3B),
 C24(H24A,H24B), C20(H20A,H20B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 N9(H9), N1(H1), N5(H5), N8(H8), N16(H16), N15(H15), N13(H13), N7(H7), C8(H8A),
  C22(H22)
2.d Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C33(H33A,H33B,H33C)
2.e Idealised tetrahedral OH refined as rotating group:
 O9(H9C)
;
_shelx_res_checksum              33867
_olex2_submission_special_instructions 'No special instructions were received'