data_2003564 _journal_name_full 'Acta Crystallographica' _journal_year 1995 _journal_volume C51 _journal_page_first 1234 _journal_page_last 1240 _publ_section_title ; Five Salts of Berberine ; _chemical_formula_moiety 'C20 H18 N O4 1+, Cl 1-, C2 H6 O, 0.5H2 O' _chemical_formula_sum 'C22 H25 Cl N O5.50' _chemical_formula_weight 426.88 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _symmetry_space_group_name_H-M 'P -1' _cell_length_a 7.3712(10) _cell_length_b 11.2724(10) _cell_length_c 13.3998(10) _cell_angle_alpha 77.587(7) _cell_angle_beta 73.299(7) _cell_angle_gamma 78.228(8) _cell_volume 1029.4(2) _cell_formula_units_Z 2 _exptl_crystal_density_diffrn 1.377 _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7 _cell_measurement_theta_max 15 _exptl_absorpt_coefficient_mu 0.222 _cell_measurement_temperature 293(2) _exptl_crystal_description 'Needles' _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_colour 'Yellow' _diffrn_measurement_device 'Enraf Nonius CAD4' _diffrn_measurement_method '2\q/\w scans' _exptl_absorpt_correction_type 'None' _diffrn_reflns_number 3788 _reflns_number_total 3616 _reflns_number_observed 1916 _reflns_observed_criterion >2sigma(I) _diffrn_reflns_av_R_equivalents 0.0165 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_standards_number 3 _diffrn_standards_interval_count 100 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_obs 0.0562 _refine_ls_wR_factor_obs 0.1534 _refine_ls_wR_factor_all 0.1879 _refine_ls_goodness_of_fit_obs 1.302 _refine_ls_goodness_of_fit_all 0.990 _refine_ls_number_reflns 3615 _refine_ls_number_parameters 277 _refine_ls_weighting_scheme ;calc w = 1/[\s^2^(F~o~^2^)+(0.0941P)^2^+0.0000P] where P = (F~o~^2^+2F~c~^2^)/3 ; _refine_ls_shift/esd_max 0.071 _refine_diff_density_max 0.590 _refine_diff_density_min -0.434 _refine_ls_extinction_method none loop_ _atom_type_symbol _atom_type_description _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag 'C' 'C' 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0033 0.001 'H' 'H' 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0000 0.000 'N' 'N' 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0061 0.003 'Cl' 'Cl' 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.1484 0.1 'O' 'O' 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0106 0.006 loop_ _atom_site_label _atom_site_occupancy _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv Cl1 1 0.3006(2) -0.16466(11) 1.19251(9) 0.0843(4) N1 1 0.1119(3) 0.6655(2) 1.0291(2) 0.0363(6) O1 1 0.2332(4) 0.6883(2) 0.5532(2) 0.0600(7) O2 1 0.1256(4) 0.8960(2) 0.5482(2) 0.0672(8) O3 1 0.1367(3) 0.4666(2) 1.3215(2) 0.0491(6) O4 1 0.3028(3) 0.2269(2) 1.3416(2) 0.0518(6) O5 1 0.3248(4) 0.3295(3) 0.7602(2) 0.0680(8) H5 1 0.4259(64) 0.2805(40) 0.7733(33) 0.082 O6 0.50 0.4026(8) 0.0143(5) 0.9589(5) 0.084(2) C1 1 0.1514(6) 0.7955(4) 0.4937(3) 0.0674(12) H11 1 0.0292(6) 0.7839(4) 0.4867(3) 0.081 H12 1 0.2358(6) 0.8120(4) 0.4235(3) 0.081 C2 1 0.1290(5) 0.8411(3) 0.6494(3) 0.0468(9) C3 1 0.1927(5) 0.7170(3) 0.6528(2) 0.0426(8) C4 1 0.0834(5) 0.8957(3) 0.7363(3) 0.0555(10) H41 1 0.0417(5) 0.9798(3) 0.7327(3) 0.067 C5 1 0.1019(5) 0.8202(3) 0.8309(3) 0.0424(8) C6 1 0.2115(5) 0.6418(3) 0.7435(2) 0.0403(8) H61 1 0.2536(5) 0.5579(3) 0.7453(2) 0.048 C7 1 0.1650(4) 0.6951(3) 0.8357(2) 0.0360(7) C8 1 0.1872(4) 0.6165(3) 0.9360(2) 0.0333(7) C9 1 -0.0066(6) 0.7898(3) 1.0257(3) 0.0544(10) H91 1 -0.1375(6) 0.7819(3) 1.0303(3) 0.065 H92 1 -0.0077(6) 0.8237(3) 1.0866(3) 0.065 C10 1 0.0648(6) 0.8753(3) 0.9288(3) 0.0598(10) H101 1 0.1825(6) 0.8983(3) 0.9320(3) 0.072 H102 1 -0.0287(6) 0.9493(3) 0.9249(3) 0.072 C11 1 0.1274(4) 0.6025(3) 1.1219(2) 0.0381(7) H111 1 0.0759(4) 0.6402(3) 1.1813(2) 0.046 C12 1 0.2191(4) 0.4801(3) 1.1340(2) 0.0340(7) C13 1 0.2818(4) 0.4984(3) 0.9441(2) 0.0343(7) H131 1 0.3363(4) 0.4643(3) 0.8829(2) 0.041 C14 1 0.2996(4) 0.4269(3) 1.0414(2) 0.0332(7) C15 1 0.3891(4) 0.3039(3) 1.0523(3) 0.0380(8) H151 1 0.4465(4) 0.2671(3) 0.9927(3) 0.046 C16 1 0.3919(4) 0.2385(3) 1.1503(3) 0.0429(8) H161 1 0.4501(4) 0.1568(3) 1.1563(3) 0.051 C17 1 0.3099(4) 0.2902(3) 1.2422(2) 0.0393(8) C18 1 0.2267(4) 0.4113(3) 1.2344(2) 0.0366(7) C19 1 0.3791(6) 0.0991(3) 1.3542(3) 0.0614(11) H191 1 0.3643(6) 0.0667(3) 1.4279(3) 0.090(8) H192 1 0.5126(6) 0.0884(3) 1.3179(3) 0.090(8) H193 1 0.3116(6) 0.0562(3) 1.3252(3) 0.090(8) C20 1 0.2591(7) 0.4940(4) 1.3760(3) 0.0789(13) H201 1 0.1828(7) 0.5321(4) 1.4352(3) 0.132(11) H202 1 0.3422(7) 0.5489(4) 1.3289(3) 0.132(11) H203 1 0.3347(7) 0.4194(4) 1.4006(3) 0.132(11) C21 1 0.2815(9) 0.2146(5) 0.6399(5) 0.114(2) H211 1 0.2820(9) 0.2199(5) 0.5674(5) 0.199(19) H212 1 0.1579(9) 0.1998(5) 0.6846(5) 0.199(19) H213 1 0.3775(9) 0.1485(5) 0.6580(5) 0.199(19) C22 1 0.3228(6) 0.3304(4) 0.6550(3) 0.0690(11) H221 1 0.4465(6) 0.3458(4) 0.6085(3) 0.083 H222 1 0.2269(6) 0.3971(4) 0.6352(3) 0.083 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 Cl1 0.0928(9) 0.0159(6) -0.0206(6) 0.0858(8) -0.0185(6) 0.0643(7) N1 0.0353(15) -0.0025(11) -0.0055(11) 0.0345(14) -0.0135(12) 0.0388(15) O1 0.075(2) -0.0036(14) -0.0107(12) 0.066(2) -0.0046(12) 0.0313(13) O2 0.079(2) -0.0021(14) -0.0160(13) 0.060(2) 0.0092(13) 0.050(2) O3 0.0481(14) -0.0007(11) -0.0070(11) 0.0569(15) -0.0172(11) 0.0406(13) O4 0.059(2) -0.0029(11) -0.0114(11) 0.0455(14) 0.0000(11) 0.0436(13) O5 0.074(2) 0.0085(14) -0.0156(14) 0.069(2) -0.0267(14) 0.059(2) O6 0.075(4) -0.012(3) -0.017(3) 0.063(3) -0.011(3) 0.109(5) C1 0.075(3) -0.002(2) -0.016(2) 0.080(3) 0.000(2) 0.038(2) C2 0.042(2) -0.009(2) -0.013(2) 0.051(2) 0.009(2) 0.042(2) C3 0.040(2) -0.006(2) -0.0076(15) 0.046(2) -0.005(2) 0.039(2) C4 0.061(2) -0.001(2) -0.018(2) 0.037(2) -0.003(2) 0.064(2) C5 0.046(2) -0.0054(15) -0.015(2) 0.033(2) -0.0060(15) 0.049(2) C6 0.041(2) -0.0014(14) -0.0089(15) 0.034(2) -0.009(2) 0.044(2) C7 0.031(2) -0.0078(13) -0.0078(14) 0.036(2) -0.0076(14) 0.043(2) C8 0.032(2) -0.0067(13) -0.0065(13) 0.035(2) -0.0115(14) 0.035(2) C9 0.067(3) 0.012(2) -0.012(2) 0.038(2) -0.021(2) 0.054(2) C10 0.082(3) 0.000(2) -0.018(2) 0.037(2) -0.013(2) 0.058(2) C11 0.043(2) -0.0072(15) -0.0094(14) 0.040(2) -0.0123(14) 0.034(2) C12 0.030(2) -0.0058(13) -0.0088(14) 0.033(2) -0.0114(14) 0.041(2) C13 0.036(2) -0.0062(14) -0.0058(13) 0.035(2) -0.0142(14) 0.034(2) C14 0.029(2) -0.0058(13) -0.0106(14) 0.035(2) -0.0098(14) 0.038(2) C15 0.032(2) -0.0001(13) -0.0070(14) 0.037(2) -0.0157(15) 0.046(2) C16 0.041(2) -0.0025(15) -0.011(2) 0.037(2) -0.009(2) 0.049(2) C17 0.034(2) -0.0053(15) -0.0115(14) 0.042(2) -0.0018(15) 0.041(2) C18 0.033(2) -0.0057(14) -0.0050(14) 0.044(2) -0.0114(14) 0.033(2) C19 0.074(3) 0.002(2) -0.019(2) 0.038(2) 0.006(2) 0.062(2) C20 0.093(3) -0.011(3) -0.033(3) 0.093(3) -0.042(3) 0.070(3) C21 0.132(5) -0.032(4) -0.036(4) 0.106(4) -0.054(4) 0.128(5) C22 0.067(3) -0.001(2) -0.014(2) 0.070(3) -0.023(2) 0.069(3)