Synthesis of diphenylamine macrocycles and their anti-inflammatory effects.
Chávez-Riveros, Alejandra; Hernández-Vázquez, Eduardo; Nieto-Camacho, Antonio; Ramírez-Apan, Teresa; Miranda, Luis D.; Organic & biomolecular chemistry 17 (2019) 1423–1435; doi:10.1039/c8ob03121e

data_7156650
_publ_section_title
;
 Synthesis of diphenylamine macrocycles and their anti-inflammatory
 effects.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1423
_journal_page_last               1435
_journal_paper_doi               10.1039/c8ob03121e
_journal_volume                  17
_journal_year                    2019
_chemical_formula_sum            'C120 H164 N20 O18'
_chemical_formula_weight         2174.70
_chemical_properties_physical    Heat-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-05-24 deposited with the CCDC.
2019-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.0176(6)
_cell_length_b                   36.9735(8)
_cell_length_c                   14.7072(3)
_cell_measurement_reflns_used    9809
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      68.21
_cell_measurement_theta_min      3.62
_cell_volume                     14691.5(5)
_computing_cell_refinement       'APEX3 v2016.1 (Bruker, 2014)'
_computing_data_collection       'APEX3 v2016.1 (Bruker, 2014)'
_computing_data_reduction        'SAINT V8.37A  (Bruker, 2014)'
_computing_molecular_graphics
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Bruker, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 0.83
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Bruker D8 Venture \k-geometry diffractometer 208039-01'
_diffrn_measurement_method       \w-scans
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27876
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.386
_diffrn_reflns_theta_min         3.624
_exptl_absorpt_coefficient_mu    0.540
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.983
_exptl_crystal_description       Prism
_exptl_crystal_F_000             4672
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.289
_exptl_crystal_size_min          0.179
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
; 
 Flack x determined using 1626 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.15(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     414
_refine_ls_number_reflns         6518
_refine_ls_number_restraints     70
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0701
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0956P)^2^+11.8017P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1767
_refine_ls_wR_factor_ref         0.1927
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_full    0.933
_reflns_Friedel_fraction_max     0.931
_reflns_number_gt                4835
_reflns_number_total             6518
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob03121e2.cif
_cod_data_source_block           337MGL17
_cod_depositor_comments          'Adding full bibliography for 7156650.cif.'
_cod_database_code               7156650
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.842
_shelx_estimated_absorpt_t_max   0.910
_shelx_res_checksum              25846
_shelx_fab_checksum              2491