#------------------------------------------------------------------------------
#$Date: 2022-11-17 11:30:58 +0200 (Thu, 17 Nov 2022) $
#$Revision: 279350 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/61/8106130.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8106130
loop_
_publ_author_name
'Zhang, Mei'
'Lou, Benyong'
'Huang, Xiaodong'
'Huang, Yali'
_publ_section_title
;
 Crystal structure of
 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium
 chloride --- 4-hydroxy-3-methoxybenzoic acid --- water (2/1/5),
 C48H54N2Cl2O17
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              291
_journal_page_last               293
_journal_paper_doi               10.1515/ncrs-2017-0293
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         '2(C20 H18 N O4), 2(C4 H4 O2), 2(Cl), 5(H2 O)'
_chemical_formula_sum            'C48 H54 Cl2 N2 O17'
_chemical_formula_weight         1001.83
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   28.3651(8)
_cell_length_b                   22.8464(6)
_cell_length_c                   7.1341(2)
_cell_measurement_reflns_used    5430
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.1720
_cell_measurement_theta_min      6.242
_cell_volume                     4623.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'SHELXL (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.2684
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_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  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            12116
_diffrn_reflns_theta_full        73.95
_diffrn_reflns_theta_max         73.95
_diffrn_reflns_theta_min         3.67
_exptl_absorpt_coefficient_mu    1.933
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.88247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2104
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.831
_refine_diff_density_min         -0.554
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4695
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0700P)²+1.8896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1179
_refine_ls_wR_factor_ref         0.1225
_reflns_number_gt                4189
_reflns_number_total             4695
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2017-0293_suppl.cif
_cod_data_source_block           lou
_cod_original_sg_symbol_Hall     -P2c2n
_cod_original_sg_symbol_H-M      Pnma
_cod_database_code               8106130
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.439449(16) 0.360804(18) 0.89645(6) 0.03139(13) Uani 1 1 d . . .
O1 O 0.09438(7) 0.2500 0.8930(2) 0.0315(4) Uani 1 2 d S . .
O2 O 0.05317(7) 0.2500 0.6249(3) 0.0426(5) Uani 1 2 d S . .
O3 O 0.25596(7) 0.2500 0.2749(3) 0.0436(5) Uani 1 2 d S . .
O4 O 0.26525(7) 0.2500 0.6487(2) 0.0367(4) Uani 1 2 d S . .
O5 O 0.33676(5) 0.49070(6) 0.6413(2) 0.0357(3) Uani 1 1 d . . .
O6 O 0.31666(5) 0.58729(6) 0.5784(2) 0.0368(3) Uani 1 1 d . . .
O7 O 0.68197(4) 0.55437(6) 0.79299(17) 0.0295(3) Uani 1 1 d . . .
O8 O 0.71289(5) 0.45147(6) 0.92508(19) 0.0328(3) Uani 1 1 d . . .
O9 O 0.41448(11) 0.2500 1.1436(3) 0.0609(7) Uani 1 2 d S . .
O12 O 0.34335(8) 0.2500 0.3979(3) 0.0647(8) Uani 1 2 d S . .
O11 O 0.35582(6) 0.35519(8) 0.5939(3) 0.0541(4) Uani 1 1 d . . .
O10 O 0.47481(7) 0.2500 0.6855(2) 0.0318(4) Uani 1 2 d S . .
N1 N 0.54008(5) 0.58017(6) 0.68287(18) 0.0233(3) Uani 1 1 d . . .
C1 C 0.09285(10) 0.2500 0.7222(3) 0.0292(5) Uani 1 2 d S . .
C2 C 0.13563(10) 0.2500 0.6024(3) 0.0286(5) Uani 1 2 d S . .
C3 C 0.17990(10) 0.2500 0.6893(3) 0.0281(5) Uani 1 2 d S . .
H3 H 0.1821 0.2500 0.8221 0.034 Uiso 1 2 calc SR . .
C4 C 0.22037(10) 0.2500 0.5819(3) 0.0286(5) Uani 1 2 d S . .
C5 C 0.13234(10) 0.2500 0.4079(3) 0.0328(6) Uani 1 2 d S . .
H5 H 0.1024 0.2500 0.3486 0.039 Uiso 1 2 calc SR . .
C6 C 0.17342(11) 0.2500 0.3006(3) 0.0360(6) Uani 1 2 d S . .
H6 H 0.1712 0.2500 0.1677 0.043 Uiso 1 2 calc SR . .
C7 C 0.21707(10) 0.2500 0.3838(3) 0.0322(6) Uani 1 2 d S . .
C8 C 0.27111(11) 0.2500 0.8489(4) 0.0395(7) Uani 1 2 d S . .
H8A H 0.3048 0.2500 0.8794 0.059 Uiso 1 2 calc SR . .
H8B H 0.2563 0.2150 0.9019 0.059 Uiso 0.50 1 calc PR . .
H8C H 0.2563 0.2850 0.9019 0.059 Uiso 0.50 1 calc PR . .
C9 C 0.29843(7) 0.52899(9) 0.5905(3) 0.0336(4) Uani 1 1 d . . .
H9A H 0.2850 0.5170 0.4684 0.040 Uiso 1 1 calc R . .
H9B H 0.2732 0.5271 0.6863 0.040 Uiso 1 1 calc R . .
C10 C 0.36409(6) 0.58293(9) 0.6112(2) 0.0278(4) Uani 1 1 d . . .
C11 C 0.37625(6) 0.52546(8) 0.6487(2) 0.0267(4) Uani 1 1 d . . .
C12 C 0.42157(6) 0.50855(8) 0.6833(2) 0.0248(3) Uani 1 1 d . . .
H12 H 0.4295 0.4688 0.7061 0.030 Uiso 1 1 calc R . .
C13 C 0.39671(6) 0.62703(8) 0.6124(2) 0.0274(4) Uani 1 1 d . . .
H13 H 0.3880 0.6664 0.5871 0.033 Uiso 1 1 calc R . .
C14 C 0.44345(6) 0.61163(8) 0.6524(2) 0.0249(3) Uani 1 1 d . . .
C15 C 0.45624(6) 0.55318(7) 0.6836(2) 0.0228(3) Uani 1 1 d . . .
C16 C 0.48061(6) 0.65846(8) 0.6695(2) 0.0274(4) Uani 1 1 d . . .
H16A H 0.4706 0.6938 0.6000 0.033 Uiso 1 1 calc R . .
H16B H 0.4848 0.6692 0.8029 0.033 Uiso 1 1 calc R . .
C17 C 0.52651(6) 0.63618(8) 0.5910(2) 0.0271(4) Uani 1 1 d . . .
H17A H 0.5233 0.6300 0.4543 0.033 Uiso 1 1 calc R . .
H17B H 0.5515 0.6657 0.6117 0.033 Uiso 1 1 calc R . .
C18 C 0.50580(6) 0.53834(7) 0.7213(2) 0.0224(3) Uani 1 1 d . . .
C19 C 0.52081(6) 0.48505(7) 0.7891(2) 0.0225(3) Uani 1 1 d . . .
H19 H 0.4981 0.4555 0.8144 0.027 Uiso 1 1 calc R . .
C20 C 0.58546(6) 0.57152(8) 0.7190(2) 0.0256(3) Uani 1 1 d . . .
H20 H 0.6073 0.6021 0.6943 0.031 Uiso 1 1 calc R . .
C21 C 0.60194(6) 0.51862(7) 0.7925(2) 0.0230(3) Uani 1 1 d . . .
C22 C 0.56892(6) 0.47297(7) 0.8223(2) 0.0231(3) Uani 1 1 d . . .
C23 C 0.58575(6) 0.41801(8) 0.8835(2) 0.0251(3) Uani 1 1 d . . .
H23 H 0.5643 0.3866 0.9024 0.030 Uiso 1 1 calc R . .
C24 C 0.63308(7) 0.40988(8) 0.9157(2) 0.0267(4) Uani 1 1 d . . .
H24 H 0.6440 0.3726 0.9550 0.032 Uiso 1 1 calc R . .
C25 C 0.66587(6) 0.45612(8) 0.8913(2) 0.0259(3) Uani 1 1 d . . .
C26 C 0.65048(6) 0.51018(8) 0.8295(2) 0.0245(3) Uani 1 1 d . . .
C27 C 0.68877(7) 0.59418(9) 0.9471(3) 0.0378(4) Uani 1 1 d . . .
H27A H 0.6585 0.6118 0.9816 0.057 Uiso 1 1 calc R . .
H27B H 0.7109 0.6251 0.9099 0.057 Uiso 1 1 calc R . .
H27C H 0.7016 0.5728 1.0548 0.057 Uiso 1 1 calc R . .
C28 C 0.73217(7) 0.39435(9) 0.9578(3) 0.0404(5) Uani 1 1 d . . .
H28A H 0.7189 0.3782 1.0737 0.061 Uiso 1 1 calc R . .
H28B H 0.7665 0.3972 0.9695 0.061 Uiso 1 1 calc R . .
H28C H 0.7242 0.3686 0.8525 0.061 Uiso 1 1 calc R . .
H10 H 0.4615 0.2811 0.7454 0.048 Uiso 1 1 d R . .
H9 H 0.4150 0.2785 1.0632 0.048 Uiso 1 1 d R . .
H11B H 0.3793 0.3526 0.6778 0.048 Uiso 1 1 d R . .
H3A H 0.2841 0.2500 0.3190 0.048 Uiso 1 2 d SR . .
H2 H 0.0302 0.2500 0.6986 0.048 Uiso 1 2 d SR . .
H12B H 0.3547 0.2792 0.4694 0.048 Uiso 0.50 1 d PR . .
H12A H 0.3629 0.2500 0.2979 0.048 Uiso 1 2 d SR . .
H11A H 0.3502 0.3931 0.6122 0.048 Uiso 1 1 d R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 O2 H2 109.4 . .
C7 O3 H3A 123.3 . .
C4 O4 C8 117.2(2) . .
C11 O5 C9 105.89(15) . .
C10 O6 C9 106.07(15) . .
C26 O7 C27 114.00(14) . .
C25 O8 C28 118.29(15) . .
H12B O12 H12A 103.2 . .
H11B O11 H11A 95.7 . .
C20 N1 C18 122.50(15) . .
C20 N1 C17 117.66(14) . .
C18 N1 C17 119.80(14) . .
O1 C1 O2 123.7(3) . .
O1 C1 C2 123.1(3) . .
O2 C1 C2 113.2(2) . .
C5 C2 C3 120.1(3) . .
C5 C2 C1 121.3(3) . .
C3 C2 C1 118.6(2) . .
C4 C3 C2 120.0(2) . .
C4 C3 H3 120.0 . .
C2 C3 H3 120.0 . .
O4 C4 C3 125.7(2) . .
O4 C4 C7 114.3(2) . .
C3 C4 C7 119.9(2) . .
C2 C5 C6 119.5(3) . .
C2 C5 H5 120.3 . .
C6 C5 H5 120.3 . .
C7 C6 C5 121.1(2) . .
C7 C6 H6 119.5 . .
C5 C6 H6 119.5 . .
O3 C7 C6 119.3(2) . .
O3 C7 C4 121.3(3) . .
C6 C7 C4 119.4(3) . .
O4 C8 H8A 109.5 . .
O4 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
O4 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
O6 C9 O5 107.90(14) . .
O6 C9 H9A 110.1 . .
O5 C9 H9A 110.1 . .
O6 C9 H9B 110.1 . .
O5 C9 H9B 110.1 . .
H9A C9 H9B 108.4 . .
C13 C10 O6 127.73(18) . .
C13 C10 C11 121.96(17) . .
O6 C10 C11 110.31(16) . .
C12 C11 O5 127.69(17) . .
C12 C11 C10 122.57(17) . .
O5 C11 C10 109.73(16) . .
C11 C12 C15 116.77(16) . .
C11 C12 H12 121.6 . .
C15 C12 H12 121.6 . .
C10 C13 C14 117.14(17) . .
C10 C13 H13 121.4 . .
C14 C13 H13 121.4 . .
C13 C14 C15 121.10(16) . .
C13 C14 C16 120.00(16) . .
C15 C14 C16 118.86(15) . .
C14 C15 C12 120.39(16) . .
C14 C15 C18 119.73(15) . .
C12 C15 C18 119.86(15) . .
C17 C16 C14 109.55(14) . .
C17 C16 H16A 109.8 . .
C14 C16 H16A 109.8 . .
C17 C16 H16B 109.8 . .
C14 C16 H16B 109.8 . .
H16A C16 H16B 108.2 . .
N1 C17 C16 110.52(14) . .
N1 C17 H17A 109.5 . .
C16 C17 H17A 109.5 . .
N1 C17 H17B 109.5 . .
C16 C17 H17B 109.5 . .
H17A C17 H17B 108.1 . .
C19 C18 N1 117.43(15) . .
C19 C18 C15 124.27(15) . .
N1 C18 C15 118.29(15) . .
C18 C19 C22 122.02(15) . .
C18 C19 H19 119.0 . .
C22 C19 H19 119.0 . .
N1 C20 C21 121.72(15) . .
N1 C20 H20 119.1 . .
C21 C20 H20 119.1 . .
C20 C21 C26 120.88(15) . .
C20 C21 C22 118.12(16) . .
C26 C21 C22 120.96(16) . .
C19 C22 C23 123.52(16) . .
C19 C22 C21 118.00(15) . .
C23 C22 C21 118.48(16) . .
C24 C23 C22 120.12(16) . .
C24 C23 H23 119.9 . .
C22 C23 H23 119.9 . .
C23 C24 C25 121.30(16) . .
C23 C24 H24 119.4 . .
C25 C24 H24 119.4 . .
O8 C25 C26 115.86(16) . .
O8 C25 C24 124.31(16) . .
C26 C25 C24 119.84(16) . .
O7 C26 C25 120.81(16) . .
O7 C26 C21 119.82(15) . .
C25 C26 C21 119.26(16) . .
O7 C27 H27A 109.5 . .
O7 C27 H27B 109.5 . .
H27A C27 H27B 109.5 . .
O7 C27 H27C 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
O8 C28 H28A 109.5 . .
O8 C28 H28B 109.5 . .
H28A C28 H28B 109.5 . .
O8 C28 H28C 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.219(3) .
O2 C1 1.322(3) .
O2 H2 0.8366 .
O3 C7 1.349(3) .
O3 H3A 0.8566 .
O4 C4 1.359(3) .
O4 C8 1.438(3) .
O5 C11 1.374(2) .
O5 C9 1.442(2) .
O6 C10 1.369(2) .
O6 C9 1.431(2) .
O7 C26 1.373(2) .
O7 C27 1.440(2) .
O8 C25 1.360(2) .
O8 C28 1.434(2) .
O9 H9 0.8673 .
O12 H12B 0.8992 .
O12 H12A 0.9033 .
O11 H11B 0.8977 .
O11 H11A 0.8896 .
O10 H10 0.9106 .
N1 C20 1.328(2) .
N1 C18 1.391(2) .
N1 C17 1.488(2) .
C1 C2 1.484(4) .
C2 C5 1.391(3) .
C2 C3 1.400(4) .
C3 C4 1.380(4) .
C3 H3 0.9500 .
C4 C7 1.416(3) .
C5 C6 1.394(4) .
C5 H5 0.9500 .
C6 C7 1.373(4) .
C6 H6 0.9500 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C13 1.368(3) .
C10 C11 1.384(3) .
C11 C12 1.365(3) .
C12 C15 1.416(2) .
C12 H12 0.9500 .
C13 C14 1.401(2) .
C13 H13 0.9500 .
C14 C15 1.402(2) .
C14 C16 1.507(2) .
C15 C18 1.471(2) .
C16 C17 1.506(3) .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 C19 1.378(2) .
C19 C22 1.412(2) .
C19 H19 0.9500 .
C20 C21 1.398(2) .
C20 H20 0.9500 .
C21 C26 1.415(2) .
C21 C22 1.418(2) .
C22 C23 1.413(2) .
C23 C24 1.375(3) .
C23 H23 0.9500 .
C24 C25 1.418(3) .
C24 H24 0.9500 .
C25 C26 1.382(3) .
C27 H27A 0.9800 .
C27 H27B 0.9800 .
C27 H27C 0.9800 .
C28 H28A 0.9800 .
C28 H28B 0.9800 .
C28 H28C 0.9800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3A O12 0.86 1.77 2.629(3) 177.0 .
O11 H11A O5 0.89 2.27 3.161(2) 176.7 .
O12 H12B O11 0.90 1.95 2.803(2) 157.5 .
O11 H11B Cl1 0.90 2.32 3.2097(19) 171.5 .
O9 H9 Cl1 0.87 2.33 3.1654(13) 161.3 .
O10 H10 Cl1 0.91 2.21 3.1111(11) 171.9 .
O2 H2 O10 0.84 1.78 2.602(3) 168.8 3_456
O12 H12A O9 0.90 1.83 2.713(3) 164.7 1_554
