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_7225085
_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 unk
_chemical_formula_moiety         'C22 H16 O3'
_chemical_formula_sum            'C22 H16 O3'
_chemical_formula_weight         328.35
_chemical_melting_point          411
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_audit_update_record
;
2016-02-16 deposited with the CCDC.
2016-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.748(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.9608(3)
_cell_length_b                   9.4348(3)
_cell_length_c                   10.0343(3)
_cell_measurement_reflns_used    4973
_cell_measurement_temperature    293
_cell_measurement_theta_max      71.1090
_cell_measurement_theta_min      4.6320
_cell_volume                     863.16(5)
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.9893
_diffrn_measured_fraction_theta_max 0.9893
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9817
_diffrn_reflns_theta_full        73.0988
_diffrn_reflns_theta_max         73.10
_diffrn_reflns_theta_min         4.81
_exptl_absorpt_coefficient_mu    0.672
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.2633
_exptl_crystal_description       plate
_exptl_crystal_F_000             344.0
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane'
_refine_diff_density_max         0.1607
_refine_diff_density_min         -0.1510
_refine_diff_density_rms         0.0304
_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            0.8057
_refine_ls_d_res_low             9.1847
_refine_ls_goodness_of_fit_ref   0.6369
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    29
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.6369
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0366
_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^)+(0.1299P)^2^+0.2307P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1175
_reflns_Friedel_coverage         0.702
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              9
_reflns_limit_k_min              -11
_reflns_limit_l_max              12
_reflns_limit_l_min              -12
_reflns_number_gt                2763
_reflns_number_total             2967
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c6ra10496g2.cif
_cod_data_source_block           exp_689
_cod_database_code               7225085
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H19 of C19, H4 of C4, H22 of C22, H3 of C3, H11 of C11, H12 of C12, H25 of
  C25, H23 of C23, {H15a,H15b} of C15, H16 of C16, H17 of C17, H24 of C24
 At 1.5 times of:
  {H21a,H21b,H21c} of C21
2.a Secondary CH2 refined with riding coordinates:
 C15(H15a,H15b)
2.b Aromatic/amide H refined with riding coordinates:
 C19(H19), C4(H4), C22(H22), C3(H3), C11(H11), C12(H12), C25(H25), C23(H23),
 C16(H16), C17(H17), C24(H24)
2.c Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c)
;