Selective Formylation of Azacalixpyridine Macrocycles and Their Transformation to Molecular Semicages.
Ren, Wen-Sheng; Zhao, Liang; Wang, Mei-Xiang; The Journal of organic chemistry 80 (2015) 9272–9278; doi:10.1021/acs.joc.5b01722

data_4036355
_publ_section_title
;
 Selective Formylation of Azacalixpyridine Macrocycles and Their
 Transformation to Molecular Semicages.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9272
_journal_page_last               9278
_journal_paper_doi               10.1021/acs.joc.5b01722
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C H Cl3, 2(C30 H26 N6)'
_chemical_formula_sum            'C61 H53 Cl3 N12'
_chemical_formula_weight         1060.50
_space_group_crystal_system      tetragonal
_space_group_IT_number           102
_space_group_name_Hall           'P 4n -2n'
_space_group_name_H-M_alt        'P 42 n m'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-03-21
_audit_creation_method
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   19.890(3)
_cell_length_b                   19.890(3)
_cell_length_c                   6.3216(13)
_cell_measurement_reflns_used    8116
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4819
_cell_measurement_theta_min      1.0238
_cell_volume                     2500.9(7)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2013)'
_computing_structure_solution
;
'XS (Sheldrick, 2013)'
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0079
_diffrn_orient_matrix_UB_12      0.0190
_diffrn_orient_matrix_UB_13      0.1569
_diffrn_orient_matrix_UB_21      0.0501
_diffrn_orient_matrix_UB_22      0.0037
_diffrn_orient_matrix_UB_23      0.0021
_diffrn_orient_matrix_UB_31      -0.0034
_diffrn_orient_matrix_UB_32      0.0498
_diffrn_orient_matrix_UB_33      -0.0062
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            19317
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         2.290
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       plate
_exptl_crystal_F_000             1108
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   1.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2974
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.130
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0573
_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^)+(0.0682P)^2^+1.1711P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1457
_refine_ls_wR_factor_ref         0.1468
_reflns_Friedel_coverage         0.835
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2914
_reflns_number_total             2974
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01722_si_002.cif
_cod_data_source_block           a
_cod_original_cell_volume        2500.9(9)
_cod_database_code               4036355
_shelxl_version_number           2013-4
_diffrn_number_total             5772
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C17) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: C17(0.25) H17(0.25)
4.a Riding coordinates:
 C17(H17)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C6(H6), C9(H9), C10(H10), C11(H11), C13(H13)
4.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              13179
_shelx_hkl_checksum              12541