A Stereospecific Total Synthesis of dl-Hexahydroapoerysopine
Fang, Da-Shu; Deng, Jun; Zheng, Jianfeng; Li, Wei-Dong Z.; Chemical Communications  (2022) –; doi:10.1039/D2CC01892F

data_7130064
_publ_section_title
;
 A Stereospecific Total Synthesis of dl-Hexahydroapoerysopine
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01892F
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H19 N O5'
_chemical_formula_sum            'C20 H19 N O5'
_chemical_formula_weight         353.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-27
_audit_creation_method
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Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_audit_update_record
;
2021-10-14 deposited with the CCDC.	2022-05-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.610(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.2614(16)
_cell_length_b                   5.0789(4)
_cell_length_c                   19.9253(17)
_cell_measurement_reflns_used    1760
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.0840
_cell_measurement_theta_min      4.0000
_cell_volume                     1757.7(3)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.0892
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.856
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.856
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            7168
_diffrn_reflns_point_group_measured_fraction_full 0.720
_diffrn_reflns_point_group_measured_fraction_max 0.598
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.176
_diffrn_reflns_theta_min         3.689
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
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_refine_diff_density_max         0.282
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 975 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         5660
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0597P)^2^+0.0983P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1507
_reflns_Friedel_coverage         0.395
_reflns_Friedel_fraction_full    0.442
_reflns_Friedel_fraction_max     0.339
_reflns_number_gt                3847
_reflns_number_total             5660
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc01892f2.cif
_cod_data_source_block           20191126-dengjun-fds-20191109
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_absolute_configuration' value 'UNK' was changed
to 'unk' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7130064
_shelx_shelxl_version_number     2014/7
_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
2.a Secondary CH2 refined with riding coordinates:
 C010(H01P,H01Q), C011(H01A,H01B), C015(H01R,H01S), C016(H01C,H01D), C018(H01E,
 H01F), C01B(H01W,H01X)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00J(H00J), C00L(H00L), C00P(H00P), C00U(H00U), C00Z(H00Z),
 C012(H012), C017(H017)
2.c Idealised Me refined as rotating group:
 C01A(H01T,H01U,H01V), C01C(H01Y,H,HA), C01D(H01G,H01H,H01I), C01E(H01J,H01K,
 H01L), C01F(H01M,H01N,H01O), C01G(H01Z,HB,HC)
;
_olex2_submission_special_instructions 'No special instructions were received'