Stereoselective synthesis of sugar-fused (or 1,2-annulated) isochromans and isochromanones by using oxa-Pictet-Spengler reaction.
Verma, Ashish Kumar; Chennaiah, Ande; Dubbu, Sateesh; Vankar, Yashwant D.; Organic & biomolecular chemistry 16 (2018) 8258–8262; doi:10.1039/c8ob01698d

data_7156406
_publ_section_title
;
 Stereoselective synthesis of sugar-fused (or 1,2-annulated) isochromans
 and isochromanones by using oxa-Pictet-Spengler reaction.
;
_journal_issue                   37
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8258
_journal_page_last               8262
_journal_paper_doi               10.1039/c8ob01698d
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C15 H20 O6'
_chemical_formula_sum            'C15 H20 O6'
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_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-10-05
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-06-06 deposited with the CCDC.
2018-09-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 92.305(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            2
_cell_length_a                   5.072(5)
_cell_length_b                   10.504(5)
_cell_length_c                   14.874(5)
_cell_measurement_reflns_used    3937
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      3.4
_cell_volume                     791.8(9)
_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    'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_unetI/netI     0.0776
_diffrn_reflns_Laue_measured_fraction_full 0.998
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_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
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_diffrn_reflns_point_group_measured_fraction_full 0.999
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_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.347
_diffrn_reflns_theta_min         3.358
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.096
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_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
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_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
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_refine_ls_abs_structure_details
;
 Flack x determined using 1115 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.0(5)
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
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_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0549
_refine_ls_shift/su_max          0.037
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0683P)^2^+0.0025P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1275
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2994
_reflns_number_total             3937
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01698d2.cif
_cod_data_source_block           16mard_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7156405--7156408.cif.
;
_cod_database_code               7156406
_shelx_shelxl_version_number     2016/6
_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.a Ternary CH refined with riding coordinates:
 C010(H010), C012(H012), C013(H013), C016(H016), C018(H018), C020(H020)
2.b Secondary CH2 refined with riding coordinates:
 C023(H02G,H02H)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C014(H014), C017(H017)
2.d Tetrahedral OH refined with riding coordinates:
 O002(H002), O003(H003), O006(H006)
2.e Idealised Me refined as rotating group:
 C021(H02A,H02B,H02C), C022(H02D,H02E,H02F)
;
_shelx_res_checksum              34135
_shelx_fab_checksum              58147
_olex2_submission_special_instructions 'No special instructions were received'