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_7225084
_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         'C31 H25 N O3'
_chemical_formula_sum            'C31 H25 N O3'
_chemical_formula_weight         459.52
_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_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_update_record
;
2014-12-27 deposited with the CCDC.
2016-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0291(3)
_cell_length_b                   12.1317(4)
_cell_length_c                   21.5315(9)
_cell_measurement_temperature    295
_cell_volume                     2358.52(15)
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8159
_diffrn_reflns_theta_full        73.4053
_diffrn_reflns_theta_max         73.41
_diffrn_reflns_theta_min         4.11
_exptl_absorpt_coefficient_mu    0.659
_exptl_crystal_density_diffrn    1.2941
_exptl_crystal_F_000             968.0
_refine_diff_density_max         0.1720
_refine_diff_density_min         -0.2798
_refine_diff_density_rms         0.0639
_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            0.8044
_refine_ls_d_res_low             10.7657
_refine_ls_goodness_of_fit_ref   0.8070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    39
_refine_ls_number_parameters     332
_refine_ls_number_reflns         4156
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.8070
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0467
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1170P)^2^+0.2462P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1346
_reflns_Friedel_coverage         0.726
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              26
_reflns_limit_l_min              -26
_reflns_number_gt                3724
_reflns_number_total             4731
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c6ra10496g2.cif
_cod_data_source_block           exp_726
_cod_original_cell_volume        2358.53(15)
_cod_database_code               7225084
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  {H25a,H25b} of C25, H6 of C6, H2 of C2, H3 of C3, H5 of C5, H28 of C28, H18
  of C18, H17 of C17, H15 of C15, H31 of C31, H12 of C12, H13 of C13, H16 of
  C16, H32 of C32, H35 of C35, H34 of C34, H33 of C33
 At 1.5 times of:
  {H29a,H29b,H29c} of C29
2.a Ternary CH refined with riding coordinates:
 C28(H28)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25a,H25b)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C3(H3), C5(H5), C18(H18), C17(H17), C15(H15), C31(H31),
 C12(H12), C13(H13), C16(H16), C32(H32), C35(H35), C34(H34), C33(H33)
2.d Idealised Me refined as rotating group:
 C29(H29a,H29b,H29c)
;