Weak C—H···<i>X</i> (<i>X</i> = O, N) hydrogen bonds in the crystal structure of dihydroberberine
Pingali, Subramanya; Donahue, James P.; Payton-Stewart, Florastina; Acta Crystallographica Section C 70 (2014) 388–391; doi:10.1107/S2053229614003751

data_2019444
_publ_section_title
;
 Weak C---H&#x00B7;&#x00B7;&#x00B7;<i>X</i> (<i>X</i> = O, N) hydrogen
 bonds in the crystal structure of dihydroberberine
;
_journal_coeditor_code           FN3163
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              388
_journal_page_last               391
_journal_paper_doi               10.1107/S2053229614003751
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C20 H19 N O4'
_chemical_formula_moiety         'C20 H19 N O4'
_chemical_formula_sum            'C20 H19 N O4'
_chemical_formula_weight         337.36
_chemical_name_common            Dihydroberberine
_chemical_name_systematic
9,10-Dimethoxy-6,8-dihydro-5<i>H</i>-1,3-dioxolo[4,5-<i>g</i>]isoquinolino[3,2-<i>a</i>]isoquinoline
_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   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 96.458(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9562(15)
_cell_length_b                   8.3067(17)
_cell_length_c                   28.343(6)
_cell_measurement_reflns_used    9822
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.4875
_cell_measurement_theta_min      2.452
_cell_volume                     1627.4(6)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            24555
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.556
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_correction_T_min  0.8504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2009)'
_exptl_crystal_colour            green--brown
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.103
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.363
_refine_ls_extinction_coef       0.046(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         3339
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0593P)^2^+0.4740P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1036
_reflns_number_gt                3120
_reflns_number_total             3339
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fn3163sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1627.3(6)
_cod_database_code               2019444
_cod_database_fobs_code          2019444
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.990
_shelx_hkl_checksum              15668
_shelx_res_checksum              70009
_shelxl_version_number           .2013