Azacalixquinarenes: From Canonical to (Poly-)Zwitterionic Macrocycles.
Pascal, Simon; Lavaud, Lucien; Azarias, Cloé; Varlot, Alexandre; Canard, Gabriel; Giorgi, Michel; Jacquemin, Denis; Siri, Olivier; The Journal of organic chemistry 84 (2019) 1387–1397; doi:10.1021/acs.joc.8b02847

data_4037564
_publ_section_title
;
 Azacalixquinarenes: From Canonical to (Poly-)Zwitterionic Macrocycles.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1387
_journal_page_last               1397
_journal_paper_doi               10.1021/acs.joc.8b02847
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C56 H80 N12 O8'
_chemical_formula_sum            'C56 H80 N12 O8'
_chemical_formula_weight         1049.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.6160(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.54012(18)
_cell_length_b                   27.5274(2)
_cell_length_c                   24.5429(2)
_cell_measurement_reflns_used    21491
_cell_measurement_temperature    250.00(10)
_cell_measurement_theta_max      70.9170
_cell_measurement_theta_min      3.6650
_cell_volume                     11564.03(18)
_computing_cell_refinement       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.18b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      250.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -38.00  51.00   1.00    5.00    --  -17.77  57.00   0.00   89
  2  \w    -52.00  48.00   1.00    5.00    --  -17.77  19.00 -60.00  100
  3  \w    -68.00 -43.00   1.00    5.00    --  -17.77 178.00 150.00   25
  4  \w    -53.00   2.00   1.00    5.00    --  -17.77 -77.00   0.00   55
  5  \w    -87.00 -39.00   1.00    5.00    --  -17.77 178.00 -30.00   48
  6  \w      3.00  59.00   1.00    5.00    --   17.77 -99.00   0.00   56
  7  \w      2.00  59.00   1.00    5.00    --   17.77 -99.00 120.00   57
  8  \w     29.00 108.00   1.00   20.00    --  101.41 -45.00 -90.00   79
  9  \w     78.00 174.00   1.00   20.00    --  101.41  45.00-150.00   96
 10  \w     83.00 109.00   1.00   20.00    --  101.41 -94.00-150.00   26
 11  \w     76.00 109.00   1.00   20.00    --  101.41 -45.00  30.00   33
 12  \w     20.00 105.00   1.00   20.00    --  101.41 -94.00 -60.00   85
 13  \w     28.00 128.00   1.00   20.00    --  101.41 -77.00 150.00  100
 14  \w     25.00 130.00   1.00   20.00    --  101.41 -30.00 120.00  105
 15  \w     86.00 119.00   1.00   20.00    --  101.41-125.00 150.00   33
 16  \w     32.00  82.00   1.00   20.00    --  101.41 -94.00  90.00   50
 17  \w     31.00  65.00   1.00   20.00    --  101.41-125.00 150.00   34
 18  \w    116.00 143.00   1.00   20.00    --  101.41  45.00   0.00   27
 19  \w     58.00 126.00   1.00   20.00    --  101.41 -77.00   0.00   68
 20  \w     70.00 178.00   1.00   20.00    --  101.41  15.00 -60.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0356640000
_diffrn_orient_matrix_UB_12      -0.0512621000
_diffrn_orient_matrix_UB_13      0.0012442000
_diffrn_orient_matrix_UB_21      -0.0817363000
_diffrn_orient_matrix_UB_22      -0.0224697000
_diffrn_orient_matrix_UB_23      -0.0050622000
_diffrn_orient_matrix_UB_31      -0.0125604000
_diffrn_orient_matrix_UB_32      0.0008021000
_diffrn_orient_matrix_UB_33      -0.0640564000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            41085
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.054
_diffrn_reflns_theta_min         3.691
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.18b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_description       prism
_exptl_crystal_F_000             4512
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.862
_refine_diff_density_min         -0.883
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     694
_refine_ls_number_reflns         11034
_refine_ls_number_restraints     132
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0845
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1793P)^2^+14.2606P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2597
_refine_ls_wR_factor_ref         0.2740
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9497
_reflns_number_total             11034
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02847_si_002.cif
_cod_data_source_block           sp038
_cod_original_cell_volume        11564.01(19)
_cod_database_code               4037564
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'c56 h80 n12 o8'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C52-C54 = C52-C53
 1.54 with sigma of 0.01
 C54-C55 = C53-C55
 1.54 with sigma of 0.01
 C55-C56
 1.54 with sigma of 0.01
 C54-C56
 2.5 with sigma of 0.01
 C53-C56
 2.5 with sigma of 0.01
 C56-C57
 1.45 with sigma of 0.01
 C55-C57
 2.5 with sigma of 0.01
 C46-C47
 1.5 with sigma of 0.01
 C39-C40
 1.45 with sigma of 0.01
 C40-C55_$1
 3.5 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C43 \\sim C44 \\sim C45 \\sim C46 \\sim C47 \\sim C48: within 1.7A with sigma
of 0.01 and sigma for terminal atoms of 0.02
C49 \\sim C50 \\sim C51 \\sim C52 \\sim C53 \\sim C54 \\sim C55 \\sim C56:
within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
C56 \\sim C57: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01
C36 \\sim C37 \\sim C38 \\sim C39: within 1.7A with sigma of 0.01 and sigma for
terminal atoms of 0.01
C35 \\sim C36: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002
C39 \\sim C40: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002
4. Others
 Fixed Sof: H52C(0.5) H52D(0.5) H52A(0.5) H52B(0.5) C53(0.5) H53A(0.5)
 H53B(0.5) C54(0.5) H54A(0.5) H54B(0.5) H55C(0.5) H55D(0.5) H55A(0.5) H55B(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,
 H29B), C30(H30A,H30B), C31(H31A,H31B), C33(H33A,H33B), C34(H34A,H34B),
 C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B),
  C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B), C45(H45A,
 H45B), C46(H46A,H46B), C47(H47A,H47B), C49(H49A,H49B), C50(H50A,H50B),
 C51(H51A,H51B), C52(H52C,H52D), C52(H52A,H52B), C53(H53A,H53B), C54(H54A,H54B),
  C55(H55C,H55D), C55(H55A,H55B), C56(H56A,H56B)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N6(H6), N7(H7), N11(H11), C3(H3), C6(H6A), C9(H9), C12(H12), C15(H15),
  C18(H18), C21(H21), C24(H24)
5.c Idealised Me refined with riding coordinates:
 C32(H32A,H32B,H32C), C40(H40A,H40B,H40C), C48(H48A,H48B,H48C), C57(H57A,H57B,
 H57C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.199
_oxdiff_exptl_absorpt_empirical_full_min 0.781