Synthesis and absolute stereochemistry assignment of enantiopure dihydrofuro- and dihydropyrano-quinoline alkaloids
Boyd, Derek R.; Sharma, Narain D.; Barr, Stephen A.; Carroll, Jonathan G.; Mackerracher, Donald; Malone, John F.; Journal of the Chemical Society, Perkin Transactions 1  (2000) 3397–; doi:10.1039/b005285j

data_7213407
_publ_section_title
;
 Synthesis and absolute stereochemistry assignment of enantiopure
 dihydrofuro- and dihydropyrano-quinoline alkaloids
;
_journal_issue                   20
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              3397
_journal_paper_doi               10.1039/b005285j
_journal_year                    2000
_chemical_formula_sum            'C16 H20 Cl N O7'
_chemical_formula_weight         747.56
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.715(2)
_cell_length_b                   18.175(5)
_cell_length_c                   21.948(5)
_cell_measurement_temperature    293(2)
_cell_volume                     3476.5(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_sigmaI/netI    0.0713
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5026
_diffrn_reflns_theta_full        55.00
_diffrn_reflns_theta_max         55.00
_diffrn_reflns_theta_min         3.16
_exptl_absorpt_coefficient_mu    2.300
_exptl_absorpt_correction_T_max  0.4243
_exptl_absorpt_correction_T_min  0.2606
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.45
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_coef       0.0010(2)
_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   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     462
_refine_ls_number_reflns         4384
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.0885
_refine_ls_shift/su_max          0.065
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1442P)^2^+5.6864P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2253
_refine_ls_wR_factor_ref         0.2506
_reflns_number_gt                3386
_reflns_number_total             4384
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b005285jsup1.cif
_cod_data_source_block           alk1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

data name '_atom_site_symmetry_multiplicit' was replaced with
'_atom_site_symmetry_multiplicity' as specified in the replacement
file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_cell_volume        3476.4(15)
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7213407