Synthesis and characterization of chiral aza-macrocycles and study of their enantiomer recognition ability for organo-phosphoric acid and phosphonic acid derivatives by (31)P NMR and fluorescence spectroscopy.
Khanvilkar, Aditya N.; Bedekar, Ashutosh V.; Organic & biomolecular chemistry 14 (2016) 2742–2748; doi:10.1039/c5ob02616d

data_7154947
_publ_section_title
;
 Synthesis and characterization of chiral aza-macrocycles and study of
 their enantiomer recognition ability for organo-phosphoric acid and
 phosphonic acid derivatives by (31)P NMR and fluorescence spectroscopy.
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2742
_journal_page_last               2748
_journal_paper_doi               10.1039/c5ob02616d
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C43 H49 N3 O4'
_chemical_formula_sum            'C43 H49 N3 O4'
_chemical_formula_weight         671.85
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-07-26
_audit_creation_method
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Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
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_audit_update_record
;
2014-07-30 deposited with the CCDC.
2016-01-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8516(2)
_cell_length_b                   13.9590(3)
_cell_length_c                   21.1978(4)
_cell_measurement_reflns_used    4403
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9870
_cell_measurement_theta_min      3.4620
_cell_volume                     3802.79(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.0851
_diffrn_measured_fraction_theta_full 1.0
_diffrn_measured_fraction_theta_max 1.0
_diffrn_measurement_details
;
  1 omega    6.00   38.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3214   77.0000    0.0000 32

  2 omega  -65.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3214   77.0000  -30.0000 115

  3 omega -109.00   -1.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      -69.6557   77.0000   30.0000 108

  4 omega   50.00   83.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -       69.6557   77.0000   90.0000 33

  5 omega   39.00   65.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -       69.6557   77.0000 -120.0000 26

  6 omega   52.00  118.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -       69.6557   77.0000  -60.0000 66

  7 omega   83.00  162.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      112.9900   77.0000  -90.0000 79

  8 omega  116.00  141.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      112.9900   77.0000  -60.0000 25

  9 omega  153.00  178.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      112.9900   77.0000   30.0000 25

 10 omega   73.00  175.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      112.9900   77.0000 -120.0000 102

 11 omega   73.00  109.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      112.9900   77.0000   30.0000 36

 12 omega  140.00  172.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      112.9900   77.0000  150.0000 32

 13 omega  100.00  170.00   1.0000    2.5400
omega____ theta____ kappa____ phi______ frames
    -      112.9900   77.0000 -150.0000 70
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0954674000
_diffrn_orient_matrix_UB_12      -0.0275703000
_diffrn_orient_matrix_UB_13      0.0400598000
_diffrn_orient_matrix_UB_21      0.0661096000
_diffrn_orient_matrix_UB_22      -0.0744960000
_diffrn_orient_matrix_UB_23      0.0356157000
_diffrn_orient_matrix_UB_31      0.0298477000
_diffrn_orient_matrix_UB_32      0.0765763000
_diffrn_orient_matrix_UB_33      0.0490824000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8447
_diffrn_reflns_theta_full        70.0301
_diffrn_reflns_theta_max         70.03
_diffrn_reflns_theta_min         3.79
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.1735
_exptl_crystal_F_000             1440.0
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethyl acetate and hexane'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.2469
_refine_diff_density_min         -0.2320
_refine_diff_density_rms         0.0466
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_d_res_high            0.8202
_refine_ls_d_res_low             11.6583
_refine_ls_goodness_of_fit_ref   1.0492
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    84
_refine_ls_number_parameters     452
_refine_ls_number_reflns         5807
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0492
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0679P)^2^+0.2110P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1215
_reflns_Friedel_coverage         0.575
_reflns_limit_h_max              15
_reflns_limit_h_min              -15
_reflns_limit_k_max              16
_reflns_limit_k_min              -16
_reflns_limit_l_max              25
_reflns_limit_l_min              -25
_reflns_number_gt                5223
_reflns_number_total             7206
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c5ob02616d2.cif
_cod_data_source_block           exp_510
_cod_depositor_comments
'Adding full bibliography for 7154946--7154947.cif.'
_cod_database_code               7154947
_chemical_oxdiff_formula         'C H N O'
_exptl_crystal_f_000'            1444.05
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C22(H22), C4(H4), C17(H17), C33(H33), C35(H35)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b), C15(H15a,H15b), C8(H8a,H8b), C21(H21a,H21b), C5(H5a,H5b),
 C6(H6a,H6b), C7(H7a,H7b), C19(H19a,H19b), C18(H18a,H18b), C20(H20a,H20b)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C32(H32), C30(H30), C31(H31), C29(H29), C28(H28), C27(H27),
 C46(H46), C43(H43), C50(H50), C44(H44), C48(H48), C40(H40), C47(H47), C49(H49),
  C41(H41), C42(H42)
2.d Idealised Me refined as rotating group:
 C34(H34a,H34b,H34c), C36(H36a,H36b,H36c)
;
_olex2_submission_special_instructions 'No special instructions were received'