Synthesis of 12-Membered Tetra-aza Macrocyclic Pyridinophanes Bearing Electron-Withdrawing Groups.
Yepremyan, Akop; Mekhail, Magy A.; Niebuhr, Brian P.; Pota, Kristof; Sadagopan, Nishanth; Schwartz, Timothy M.; Green, Kayla N.; The Journal of organic chemistry 85 (2020) 4988–4998; doi:10.1021/acs.joc.0c00188

data_4038126
_publ_section_title
;
 Synthesis of 12-Membered Tetra-aza Macrocyclic Pyridinophanes Bearing
 Electron-Withdrawing Groups.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4988
_journal_page_last               4998
_journal_paper_doi               10.1021/acs.joc.0c00188
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C11 H20 Cl N4, Cl, 2(C F3 O3 S)'
_chemical_formula_sum            'C13 H20 Cl2 F6 N4 O6 S2'
_chemical_formula_weight         577.355
_chemical_name_common            Fe(L8)
_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'
_symmetry_Int_Tables_number      14
_audit_creation_date             2019-11-07
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.10.31 svn.r3677 for OlexSys, GUI svn.r5972)
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.471(1)
_cell_length_b                   7.8357(7)
_cell_length_c                   24.225(3)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      36.3154
_cell_measurement_theta_min      2.4365
_cell_volume                     2177.3(4)
_computing_cell_refinement       'SAINT V8.38A (Bruker Nano, Inc., 2017)'
_computing_data_collection
'Bruker Instrument Service vV6.2.11 RC6 (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.38A (Bruker Nano, Inc., 2017)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3-alpha (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3-alpha (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.9990
_diffrn_measured_fraction_theta_max 0.9968
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scan'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.9990
_diffrn_reflns_Laue_measured_fraction_max 0.9968
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            50473
_diffrn_reflns_point_group_measured_fraction_full 0.9990
_diffrn_reflns_point_group_measured_fraction_max 0.9968
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         36.30
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.581
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1179.024
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.135
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_refine_ls_goodness_of_fit_ref   1.0641
_refine_ls_hydrogen_treatment    constr
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_refine_ls_number_constraints    20
_refine_ls_number_parameters     359
_refine_ls_number_reflns         10493
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0641
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0326P)^2^+0.6561P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0710
_refine_ls_wR_factor_ref         0.0778
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              19
_reflns_limit_h_min              -19
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              40
_reflns_limit_l_min              0
_reflns_number_gt                8590
_reflns_number_total             10493
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo0c00188_si_009.cif
_cod_data_source_block           MM__030419
_cod_depositor_comments
;
The following automatic conversions were performed:

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/ACS/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 

 Adding full bibliography for 4038125--4038126.cif.
;
_cod_database_code               4038126
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.99994(6)
 0.00006(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'