Synthesis of enantiomerically pure helicene-like mono 1,3-oxazines from 1,1’-binaphthyl-2,2’,7-triol and study of their chiroptical properties
Bedekar, Ashutosh; Mothuku, Shyam Sundar; RSC Adv.  (2016) –; doi:10.1039/C6RA10496G

data_7225083
_publ_section_title
;
 Synthesis of enantiomerically pure helicene-like mono 1,3-oxazines from
 1,1&#x2019;-binaphthyl-2,2&#x2019;,7-triol and study of their chiroptical
 properties
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA10496G
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C67 H66 N4 O12'
_chemical_formula_sum            'C67 H66 N4 O12'
_chemical_formula_weight         1119.12
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-09-10
_audit_creation_method
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2014-09-11 deposited with the CCDC.
2016-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                97.804(3)
_cell_angle_beta                 104.923(2)
_cell_angle_gamma                100.186(2)
_cell_formula_units_Z            1
_cell_length_a                   9.0356(2)
_cell_length_b                   10.3472(3)
_cell_length_c                   16.0067(5)
_cell_measurement_reflns_used    9891
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.1610
_cell_measurement_theta_min      4.3850
_cell_volume                     1397.14(7)
_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
;
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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.0851
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
  1 omega  -47.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000   60.0000 29

  2 omega  -56.00  -25.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   50.0000  -60.0000 31

  3 omega  -13.00   16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000   60.0000 29

  4 omega -110.00  -67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -64.0000  150.0000 43

  5 omega  -71.00  -35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000  -30.0000 36

  6 omega  -20.00   23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   50.0000  -60.0000 43

  7 omega -119.00  -74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000  -30.0000 45

  8 omega   16.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   19.0000  -30.0000 113

  9 omega  -16.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -38.0000  150.0000 98

 10 omega  -13.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000    0.0000 81

 11 omega   39.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  120.0000 41

 12 omega   30.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000 -180.0000 83

 13 omega   30.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000    0.0000 57

 14 omega   55.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000   90.0000 48

 15 omega  149.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -12.0000 -150.0000 29

 16 omega   41.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  150.0000 49

 17 omega   59.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000  -30.0000 33

 18 omega   50.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000   30.0000 26

 19 omega   40.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000 -180.0000 44

 20 omega   58.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000 -180.0000 26

 21 omega  123.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   38.0000  120.0000 26

 22 omega   59.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000  -90.0000 25

 23 omega   67.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000 -150.0000 26

 24 omega   69.00   95.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000   60.0000 26

 25 omega   56.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -12.0000 -150.0000 26

 26 omega  109.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -12.0000 -150.0000 26

 27 omega  104.00  130.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   25.0000  150.0000 26

 28 omega   44.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -92.0000  -60.0000 42

 29 omega   44.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -180.0000 72

 30 omega   69.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -90.0000 42

 31 omega   42.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000   30.0000 35

 32 omega   42.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000  150.0000 50

 33 omega   39.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000 -120.0000 53

 34 omega   49.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -92.0000 -150.0000 25

 35 omega   59.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000   90.0000 55

 36 omega   52.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  150.0000 51

 37 omega   91.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000  -90.0000 86

 38 omega   79.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -64.0000   30.0000 38

 39 omega   82.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000    0.0000 34

 40 omega   94.00  152.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000 -150.0000 58

 41 omega   79.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   25.0000   60.0000 43

 42 omega  133.00  159.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   25.0000   60.0000 26

 43 omega   44.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -60.0000 32

 44 omega   91.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -60.0000 25

 45 omega   58.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  -30.0000 26

 46 omega   48.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  -90.0000 44

 47 omega   51.00  127.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -64.0000  -60.0000 76

 48 omega   59.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  -60.0000 25

 49 omega  123.00  173.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   64.0000  -60.0000 50

 50 omega  109.00  134.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000 -150.0000 25

 51 omega  110.00  135.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -64.0000   90.0000 25

 52 omega   86.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   38.0000 -150.0000 26

 53 omega  111.00  136.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000   60.0000 25

 54 omega   71.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000 -180.0000 26
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0100358000
_diffrn_orient_matrix_UB_12      -0.0826464000
_diffrn_orient_matrix_UB_13      -0.0851891000
_diffrn_orient_matrix_UB_21      0.0974247000
_diffrn_orient_matrix_UB_22      0.1254480000
_diffrn_orient_matrix_UB_23      -0.0181119000
_diffrn_orient_matrix_UB_31      0.1521354000
_diffrn_orient_matrix_UB_32      -0.0343330000
_diffrn_orient_matrix_UB_33      0.0520577000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14244
_diffrn_reflns_theta_full        73.05
_diffrn_reflns_theta_max         73.05
_diffrn_reflns_theta_min         4.42
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_T_max  0.849
_exptl_absorpt_correction_T_min  0.806
_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            colorless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             591.9
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: alcohol'
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.06(15)
_refine_ls_extinction_coef       0.0049(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     778
_refine_ls_number_reflns         7223
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0836P)^2^+0.1013P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1200
_reflns_number_gt                7026
_reflns_number_total             11186
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra10496g2.cif
_cod_data_source_block           exp_605
_cod_original_cell_volume        1397.13(7)
_cod_database_code               7225083
_chemical_oxdiff_formula         'C H N O'
_reflns_odcompleteness_completeness 89.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_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, All O(H) groups
2. Others
 Fixed Sof: C5(0.33333) C82(0.33333) C18(0.33333)
3.a Ternary CH refined with riding coordinates:
 C64(H64), C22(H22), C13(H13), C14(H14), C19(H19), C62(H62), C2(H2), C60(H60),
 C68(H68)
3.b Secondary CH2 refined with riding coordinates:
 C73(H73A,H73B), C72(H72A,H72B), C24(H24A,H24B), C61(H61A,H61B), C3(H3A,H3B),
 C21(H21A,H21B), C69(H69A,H69B), C23(H23A,H23B), C70(H70A,H70B), C16(H16A,H16B),
  C1(H1A,H1B), C76(H76A,H76B)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C38(H38), C32(H32), C58(H58), C48(H48), C10(H10), C55(H55), C33(H33),
 C35(H35), C15(H15), C36(H36), C47(H47), C42(H42), C74(H74), C45(H45), C43(H43),
  C44(H44)
3.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C78(H78A,H78B,H78C), C81(H81A,H81B,
 H81C)
3.e Idealised tetrahedral OH refined as rotating group:
 O51(H51), O50(H50), O52(H52)
;
_olex2_submission_special_instructions 'No special instructions were received'