A concise asymmetric total synthesis for structure elucidation of 5,6-secoiridoid from Incarvillea argute
Zhang, Weidong; Fu, Jianjun; Liu, Zhiqian; Jin, Huizi; Zhang, Shoude; Sun, Qingyan; RSC Adv.  (2016) –; doi:10.1039/C6RA15153A

data_7226010
_publ_section_title
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 A concise asymmetric total synthesis for structure elucidation of
 5,6-secoiridoid from Incarvillea argute
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_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA15153A
_journal_year                    2016
_chemical_formula_moiety         'C15 H18 N4 O6'
_chemical_formula_sum            'C15 H18 N4 O6'
_chemical_formula_weight         350.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-10-30
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2015-05-25 deposited with the CCDC.
2016-07-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.9460(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.76250(10)
_cell_length_b                   23.3095(5)
_cell_length_c                   11.9536(2)
_cell_measurement_reflns_used    4914
_cell_measurement_temperature    130
_cell_measurement_theta_max      69.41
_cell_measurement_theta_min      4.26
_cell_volume                     1558.29(5)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8065
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.738
_diffrn_reflns_theta_min         4.257
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.995
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.4285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1315 before and 0.0642 after correction.
The Ratio of minimum to maximum transmission is 0.5688.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.796
_refine_diff_density_min         -0.850
_refine_diff_density_rms         0.347
_refine_ls_extinction_coef       0.0121(12)
_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   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2854
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.218
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0554
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0982P)^2^+0.5124P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1453
_refine_ls_wR_factor_ref         0.1594
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2683
_reflns_number_total             2854
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra15153a2.cif
_cod_data_source_block           dm14223
_cod_database_code               7226010
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.755
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(N2) \\sim Ueq, Uanis(C5) \\sim Ueq: with sigma of 0.001 and sigma for
terminal atoms of 0.002
3.a Ternary CH refined with riding coordinates:
 C8(H8), C1(H1), C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C6(H6A,H6B), C3(H3A,H3B), C5(H5A,H5B)
3.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C12(H12), C13(H13), C15(H15)
3.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              14507
_olex2_submission_special_instructions 'No special instructions were received'