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_7239789
_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_absolute_configuration syn
_chemical_formula_moiety         '0.5(C24 H38 N16 O4), C2 F3 O2, 2(C H4 O)'
_chemical_formula_sum            'C16 H27 F3 N8 O6'
_chemical_formula_weight         484.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_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                90
_cell_angle_beta                 119.248(12)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.515(10)
_cell_length_b                   8.492(4)
_cell_length_c                   25.298(10)
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      3.23
_cell_volume                     4595(3)
_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      100.13
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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  0.0297
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            25354
_diffrn_reflns_point_group_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.088
_diffrn_reflns_theta_min         2.889
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0526 before and 0.0477 after correction. The Ratio of minimum to maximum transmission is 0.9095. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       block
_exptl_crystal_F_000             2032
_exptl_crystal_size_max          0.565
_exptl_crystal_size_mid          0.482
_exptl_crystal_size_min          0.386
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 3064 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     603
_refine_ls_number_reflns         9347
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0536
_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^)+(0.0750P)^2^+4.9482P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1309
_refine_ls_wR_factor_ref         0.1421
_reflns_Friedel_coverage         0.855
_reflns_Friedel_fraction_full    0.880
_reflns_Friedel_fraction_max     0.852
_reflns_number_gt                7912
_reflns_number_total             9347
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ra08056b2.cif
_cod_data_source_block           3x3
_cod_depositor_comments
'Adding full bibliography for 7239788--7239792.cif.'
_cod_database_code               7239789
_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
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C21(H21A,H21B), C12(H12A,H12B), C23(H23A,H23B), C4(H4A,H4B),
 C16(H16A,H16B), C2(H2A,H2B), C24(H24A,H24B), C11(H11A,H11B), C19(H19A,H19B),
 C3(H3A,H3B), C17(H17A,H17B), C1(H1A,H1B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N14(H14), N9(H9), N5(H5), N8(H8), N6(H6), N16(H16), N13(H13),
 C20(H20), C8(H8A)
2.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C), C30(H30A,H30B,
 H30C)
2.d Idealised tetrahedral OH refined as rotating group:
 O12(H12), O10(H10), O9(H9C), O11(H11)
;
_shelx_res_checksum              30007
_olex2_submission_special_instructions 'No special instructions were received'