A unified total synthesis of benzo[<i>d</i>][1,3]dioxole-type benzylisoquinoline alkaloids of aporphines, coptisines, and dibenzopyrrocolines.
Lv, Jie; Li, Zhi-Hong; Deng, An-Jun; Qin, Hai-Lin; Organic & biomolecular chemistry 20 (2022) 658–666; doi:10.1039/d1ob02258j

data_7158439
_publ_section_title
;
 A unified total synthesis of benzo[<i>d</i>][1,3]dioxole-type
 benzylisoquinoline alkaloids of aporphines, coptisines, and
 dibenzopyrrocolines.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              658
_journal_page_last               666
_journal_paper_doi               10.1039/d1ob02258j
_journal_volume                  20
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'Cl, C21 H20 N O6'
_chemical_formula_sum            'C21 H20 Cl N O6'
_chemical_formula_weight         417.83
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-04 deposited with the CCDC.	2021-12-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.64130(10)
_cell_length_b                   12.87260(10)
_cell_length_c                   25.5684(4)
_cell_measurement_reflns_used    14014
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      78.8820
_cell_measurement_theta_min      5.0940
_cell_volume                     3831.52(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      294.15
_diffrn_detector                 pilatus
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -25.00  94.00   0.50    2.50    --    5.00  51.00 101.00  238
  2  \w    -84.00  35.00   0.50    2.50    --    5.00 -51.00 -44.00  238
  3  \w   -138.00 -18.00   0.50    2.50    --  -48.80 -51.00 -44.00  240
  4  \w    -79.00  41.00   0.50    2.50    --  -48.80  51.00 101.00  240
  5  \w   -199.00 -80.00   0.50    5.50    -- -110.00 -51.00 -44.00  238
  6  \w   -140.00 -21.00   0.50    5.50    -- -110.00  51.00 101.00  238
  7  \w    -79.00  41.00   0.50    2.50    --  -48.80  57.00-180.00  240
  8  \w   -138.00 -18.00   0.50    2.50    --  -48.80 -57.00   0.00  240
  9  \w   -168.00 -21.00   0.50    5.50    -- -110.00  19.00 -30.00  294
 10  \w   -144.00 -21.00   0.50    5.50    -- -110.00  72.00 -30.00  246
 11  \w   -140.00 -21.00   0.50    5.50    -- -110.00  57.00 -30.00  238
 12  \w   -199.00 -52.00   0.50    5.50    -- -110.00 -19.00 -30.00  294
 13  \w   -144.00 -21.00   0.50    5.50    -- -110.00  72.00  90.00  246
 14  \w   -199.00 -77.00   0.50    5.50    -- -110.00 -38.00  90.00  244
 15  \w   -199.00 -80.00   0.50    5.50    -- -110.00 -57.00-180.00  238
 16  \w    -98.00 -62.00   0.50    5.50    -- -110.00  38.00 -30.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Xtalab P200'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1104166000
_diffrn_orient_matrix_UB_12      0.0016357000
_diffrn_orient_matrix_UB_13      0.0332454000
_diffrn_orient_matrix_UB_21      -0.0243133000
_diffrn_orient_matrix_UB_22      -0.1119408000
_diffrn_orient_matrix_UB_23      0.0181827000
_diffrn_orient_matrix_UB_31      0.0687540000
_diffrn_orient_matrix_UB_32      -0.0423371000
_diffrn_orient_matrix_UB_33      -0.0468325000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            19537
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         87.150
_diffrn_reflns_theta_min         3.457
_diffrn_source                   Rotating-anode
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.117
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1419 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(7)
_refine_ls_extinction_coef       0.00056(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4122
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.195
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0236P)^2^+5.5103P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1225
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.921
_reflns_number_gt                3753
_reflns_number_total             4122
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02258j3.cif
_cod_data_source_block           p20210630a
_cod_depositor_comments
'Adding full bibliography for 7158438--7158439.cif.'
_cod_database_code               7158439
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.816
_shelx_estimated_absorpt_t_min   0.728
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 N1(H1), C5(H5), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C6(H6A,H6B), C11(H11A,H11B), C15(H15A,H15B), C16(H16A,H16B),
 C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C9(H9), C18(H18)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_shelx_res_checksum              60897
_shelx_hkl_checksum              4971
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.976
_oxdiff_exptl_absorpt_empirical_full_min 0.573