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_4038125
_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         'C132 H204 Cl36 Cu12 N48 O49.66'
_chemical_formula_sum            'C132 H204 Cl36 Cu12 N48 O49.66'
_chemical_formula_weight         5296.85
_chemical_melting_point          ?
_chemical_name_common            none
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-12-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.232(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   26.405(3)
_cell_length_b                   29.054(3)
_cell_length_c                   13.1898(11)
_cell_measurement_reflns_used    9841
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.845
_cell_measurement_theta_min      2.880
_cell_volume                     9763.4(17)
_computing_cell_refinement       'Apex3 (Bruker AXS Inc., 2017)'
_computing_data_collection       'Apex3 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_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 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      99.89
_diffrn_detector_area_resol_mean 10.24
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type
;
 Bruker D8 Quest with Photon 100 CMOS Detector
;
_diffrn_measurement_method
;
 \f and \w scans with 1.0 deg/frame and 40 seconds of
 exposure time. Detector was at 60mm from crystal.
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0733
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            65370
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        22.483
_diffrn_reflns_theta_max         22.483
_diffrn_reflns_theta_min         2.903
_diffrn_source                   'fine-focused sealed tube'
_exptl_absorpt_coefficient_mu    1.8590
_exptl_absorpt_correction_T_max  0.7710
_exptl_absorpt_correction_T_min  0.7040
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.802
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       Block
_exptl_crystal_F_000             5378.6
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.079
_exptl_transmission_factor_max   22.48
_exptl_transmission_factor_min   2.88
_refine_diff_density_max         2.314
_refine_diff_density_min         -1.030
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     721
_refine_ls_number_reflns         6398
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0617
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0208P)^2^+246.7035P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1309
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4942
_reflns_number_total             6398
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00188_si_008.cif
_cod_data_source_block           l8cu_apex2_040318
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'not measured' was changed
to '?' -- the value is undefined or not given.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4038125--4038126.cif.
;
_cod_original_cell_volume        9763.6(15)
_cod_database_code               4038125
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.7453
_shelx_estimated_absorpt_t_min   0.6650
_exptl_absorpt_special_details
;
 The crystal was mounted using Paratone-N oil (cryoprotectant)
 on the tip of MiTeGen MicroLoops LD. It was placed on magnetic 
 head of goniometer directly into the cold gas stream of a 
 liquid-nitrogen based cryostat.
;
_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. Uiso/Uaniso restraints and constraints
C24: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
H2 \\sim C24: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
3. Rigid body (RIGU) restrains
 O6, O8, O7, O5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: O15(0.5) O12(0.5) O14(0.5) O13(0.5)
5.a Ternary CH refined with riding coordinates:
 N8(H8), N10(H10), N3(H3), N14(H14), N12(H12), N1(H1), N2(H2), N6(H6),
 N11(H11), N7(H7)
5.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C11(H11A,H11B), C7(H7A,H7B), C8(H8A,H8B), C25(H25A,H25B),
 C10(H10A,H10B), C12(H12A,H12B), C9(H9A,H9B), C18(H18A,H18B), C19(H19A,H19B),
 C23(H23A,H23B), C20(H20A,H20B), C22(H22A,H22B), C31(H31A,H31B), C30(H30A,H30B),
  C29(H29A,H29B), C21(H21A,H21B), C24(H24A,H24B)
5.c Aromatic/amide H refined with riding coordinates:
 C27(H27), C4(H4), C16(H16), C2(H2A), C33(H33), C14(H14A)
;
_shelx_res_checksum              76159
_shelx_hkl_checksum              31332
_olex2_submission_special_instructions 'No special instructions were received'