#------------------------------------------------------------------------------
#$Date: 2016-01-09 12:38:20 +0200 (Sat, 09 Jan 2016) $
#$Revision: 173766 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/31/7223119.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_7223119
loop_
_publ_author_name
'Stepanovs, D.'
'Jure, M.'
'Yanichev, A.'
'Belyakov, S.'
'Mishnev, A.'
_publ_section_title
;
 Molecular salts of propranolol with dicarboxylic acids: diversity of
 stoichiometry, supramolecular structures and physicochemical properties
;
_journal_issue                   47
_journal_name_full               CrystEngComm
_journal_page_first              9023
_journal_paper_doi               10.1039/C5CE01408E
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C16 H22 N O2, 0.5(C4 H4 O4), 0.5(C4 H2 O4)'
_chemical_formula_sum            'C20 H25 N O6'
_chemical_formula_weight         375.41
_chemical_name_common            'Propranolol fumarate (1:1)'
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-06-16 deposited with the CCDC.
2015-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                97.3910(10)
_cell_angle_beta                 102.2400(10)
_cell_angle_gamma                109.8990(10)
_cell_formula_units_Z            2
_cell_length_a                   8.6157(2)
_cell_length_b                   9.9155(2)
_cell_length_c                   13.1345(4)
_cell_measurement_reflns_used    6761
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1006.17(4)
_computing_cell_refinement       'HKL Scalepack (Otwinovski & Minor, 1997)'
_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinovski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material
;
SHELXL-97 (Sheldrick, 2008), 
PLATON (Spek, 2009) and publCIF (Westrip, 2010)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2011 (Burla, 2012)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6668
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.04
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         4597
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0556P)²+0.3863P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1207
_refine_ls_wR_factor_ref         0.1273
_reflns_number_gt                3915
_reflns_number_total             4597
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ce01408e2.cif
_cod_data_source_block           pro-fum-1-1
_cod_depositor_comments
'Adding full bibliography for 7223119--7223124.cif.'
_cod_database_code               7223119
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
O27 O 0.62720(14) -0.25019(11) 0.39789(8) 0.0336(2) Uani 1 1 d .
O28 O 0.57395(17) -0.22786(11) 0.55603(8) 0.0420(3) Uani 1 1 d .
C25 C 0.53203(19) -0.46476(15) 0.46522(10) 0.0286(3) Uani 1 1 d .
H25 H 0.5477 -0.5183 0.4074 0.034 Uiso 1 1 calc R
C26 C 0.58065(18) -0.30279(15) 0.47499(10) 0.0280(3) Uani 1 1 d .
O22 O 0.46135(15) -0.31761(12) 0.13828(8) 0.0382(3) Uani 1 1 d .
O21 O 0.63857(16) -0.40669(13) 0.23217(9) 0.0413(3) Uani 1 1 d .
C23 C 0.54288(19) -0.39613(15) 0.14370(11) 0.0305(3) Uani 1 1 d .
C24 C 0.5452(2) -0.49419(16) 0.04832(12) 0.0334(3) Uani 1 1 d .
H24 H 0.6136 -0.5492 0.0579 0.040 Uiso 1 1 calc R
O11 O 0.13442(12) -0.00209(10) 0.22085(8) 0.0284(2) Uani 1 1 d .
O15 O 0.30058(14) -0.06360(11) 0.41212(8) 0.0314(2) Uani 1 1 d .
N16 N 0.61786(15) 0.01837(14) 0.36235(9) 0.0262(2) Uani 1 1 d .
C14 C 0.45557(17) -0.01991(15) 0.27788(10) 0.0257(3) Uani 1 1 d .
H14A H 0.4637 -0.0690 0.2115 0.031 Uiso 1 1 calc R
H14B H 0.4386 0.0694 0.2664 0.031 Uiso 1 1 calc R
C9 C 0.01382(17) 0.15507(14) 0.14820(10) 0.0253(3) Uani 1 1 d .
C1 C -0.00138(17) 0.00765(14) 0.15119(10) 0.0250(3) Uani 1 1 d .
C12 C 0.13710(18) -0.14394(14) 0.22603(11) 0.0279(3) Uani 1 1 d .
H12A H 0.1341 -0.1947 0.1569 0.033 Uiso 1 1 calc R
H12B H 0.0387 -0.2026 0.2473 0.033 Uiso 1 1 calc R
C17 C 0.77544(19) 0.11370(17) 0.33506(12) 0.0330(3) Uani 1 1 d .
H17 H 0.7693 0.0718 0.2619 0.040 Uiso 1 1 calc R
C10 C -0.12153(18) 0.17654(17) 0.07834(11) 0.0295(3) Uani 1 1 d .
C4 C -0.26758(19) 0.05342(19) 0.01629(11) 0.0349(3) Uani 1 1 d .
H4 H -0.3581 0.0672 -0.0279 0.042 Uiso 1 1 calc R
C13 C 0.30258(18) -0.11956(14) 0.30825(10) 0.0264(3) Uani 1 1 d .
H13 H 0.3130 -0.2151 0.3075 0.032 Uiso 1 1 calc R
C2 C -0.14181(18) -0.10980(16) 0.08825(11) 0.0313(3) Uani 1 1 d .
H2 H -0.1487 -0.2052 0.0897 0.038 Uiso 1 1 calc R
C8 C 0.15804(19) 0.27810(15) 0.21210(11) 0.0303(3) Uani 1 1 d .
H8 H 0.2460 0.2643 0.2588 0.036 Uiso 1 1 calc R
C3 C -0.27622(19) -0.08521(18) 0.02103(12) 0.0365(3) Uani 1 1 d .
H3 H -0.3724 -0.1652 -0.0208 0.044 Uiso 1 1 calc R
C5 C -0.1045(2) 0.32295(18) 0.07271(12) 0.0377(3) Uani 1 1 d .
H5 H -0.1910 0.3393 0.0266 0.045 Uiso 1 1 calc R
C7 C 0.1686(2) 0.41759(17) 0.20545(13) 0.0389(4) Uani 1 1 d .
H7 H 0.2631 0.4982 0.2482 0.047 Uiso 1 1 calc R
C18 C 0.9330(2) 0.1090(2) 0.40880(15) 0.0519(5) Uani 1 1 d .
H18A H 0.9235 0.0088 0.4033 0.078 Uiso 1 1 calc R
H18C H 0.9426 0.1510 0.4810 0.078 Uiso 1 1 calc R
H18B H 1.0332 0.1641 0.3890 0.078 Uiso 1 1 calc R
C6 C 0.0367(2) 0.43934(18) 0.13403(14) 0.0440(4) Uani 1 1 d .
H6 H 0.0464 0.5343 0.1287 0.053 Uiso 1 1 calc R
C19 C 0.7790(3) 0.2674(2) 0.3392(2) 0.0580(5) Uani 1 1 d .
H19A H 0.6759 0.2638 0.2913 0.087 Uiso 1 1 calc R
H19C H 0.8768 0.3252 0.3184 0.087 Uiso 1 1 calc R
H19B H 0.7866 0.3112 0.4106 0.087 Uiso 1 1 calc R
H21 H 0.629(3) -0.348(3) 0.292(2) 0.073(7) Uiso 1 1 d .
H16A H 0.610(2) 0.0610(19) 0.4217(15) 0.034(4) Uiso 1 1 d .
H16B H 0.628(2) -0.066(2) 0.3756(14) 0.039(5) Uiso 1 1 d .
H15 H 0.319(3) 0.041(3) 0.4169(18) 0.067(6) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C25 C25 C26 123.09(15) 2_646
C25 C25 H25 118.5 2_646
C26 C25 H25 118.5 .
O28 C26 O27 123.90(13) .
O28 C26 C25 119.22(12) .
O27 C26 C25 116.87(11) .
C23 O21 H21 109.9(15) .
O22 C23 O21 125.24(13) .
O22 C23 C24 123.16(14) .
O21 C23 C24 111.60(12) .
C24 C24 C23 122.54(17) 2_645
C24 C24 H24 118.7 2_645
C23 C24 H24 118.7 .
C1 O11 C12 118.62(10) .
C13 O15 H15 106.8(13) .
C14 N16 C17 113.75(10) .
C14 N16 H16A 109.4(12) .
C17 N16 H16A 110.1(12) .
C14 N16 H16B 108.3(12) .
C17 N16 H16B 110.5(12) .
H16A N16 H16B 104.3(16) .
N16 C14 C13 111.35(10) .
N16 C14 H14A 109.4 .
C13 C14 H14A 109.4 .
N16 C14 H14B 109.4 .
C13 C14 H14B 109.4 .
H14A C14 H14B 108.0 .
C8 C9 C10 119.74(13) .
C8 C9 C1 122.17(12) .
C10 C9 C1 118.09(12) .
O11 C1 C2 124.93(12) .
O11 C1 C9 113.90(11) .
C2 C1 C9 121.17(12) .
O11 C12 C13 106.51(10) .
O11 C12 H12A 110.4 .
C13 C12 H12A 110.4 .
O11 C12 H12B 110.4 .
C13 C12 H12B 110.4 .
H12A C12 H12B 108.6 .
C19 C17 C18 113.08(16) .
C19 C17 N16 110.52(12) .
C18 C17 N16 108.94(12) .
C19 C17 H17 108.1 .
C18 C17 H17 108.1 .
N16 C17 H17 108.1 .
C4 C10 C9 119.69(13) .
C4 C10 C5 122.04(13) .
C9 C10 C5 118.27(14) .
C3 C4 C10 120.27(13) .
C3 C4 H4 119.9 .
C10 C4 H4 119.9 .
O15 C13 C12 111.57(11) .
O15 C13 C14 111.60(11) .
C12 C13 C14 110.11(11) .
O15 C13 H13 107.8 .
C12 C13 H13 107.8 .
C14 C13 H13 107.8 .
C1 C2 C3 119.54(14) .
C1 C2 H2 120.2 .
C3 C2 H2 120.2 .
C7 C8 C9 120.23(14) .
C7 C8 H8 119.9 .
C9 C8 H8 119.9 .
C4 C3 C2 121.22(14) .
C4 C3 H3 119.4 .
C2 C3 H3 119.4 .
C6 C5 C10 120.77(14) .
C6 C5 H5 119.6 .
C10 C5 H5 119.6 .
C8 C7 C6 120.22(15) .
C8 C7 H7 119.9 .
C6 C7 H7 119.9 .
C17 C18 H18A 109.5 .
C17 C18 H18C 109.5 .
H18A C18 H18C 109.5 .
C17 C18 H18B 109.5 .
H18A C18 H18B 109.5 .
H18C C18 H18B 109.5 .
C5 C6 C7 120.74(14) .
C5 C6 H6 119.6 .
C7 C6 H6 119.6 .
C17 C19 H19A 109.5 .
C17 C19 H19C 109.5 .
H19A C19 H19C 109.5 .
C17 C19 H19B 109.5 .
H19A C19 H19B 109.5 .
H19C C19 H19B 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O27 C26 1.2744(17) .
O28 C26 1.2411(16) .
C25 C25 1.321(3) 2_646
C25 C26 1.4957(19) .
C25 H25 0.9300 .
O22 C23 1.2124(18) .
O21 C23 1.3134(18) .
O21 H21 0.96(3) .
C23 C24 1.4919(19) .
C24 C24 1.309(3) 2_645
C24 H24 0.9300 .
O11 C1 1.3643(16) .
O11 C12 1.4245(15) .
O15 C13 1.4111(16) .
O15 H15 0.98(2) .
N16 C14 1.4842(17) .
N16 C17 1.5116(18) .
N16 H16A 0.864(18) .
N16 H16B 0.91(2) .
C14 C13 1.5201(19) .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C9 C8 1.414(2) .
C9 C10 1.4187(18) .
C9 C1 1.4290(18) .
C1 C2 1.3684(19) .
C12 C13 1.5175(18) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C17 C19 1.508(2) .
C17 C18 1.510(2) .
C17 H17 0.9800 .
C10 C4 1.415(2) .
C10 C5 1.422(2) .
C4 C3 1.361(2) .
C4 H4 0.9300 .
C13 H13 0.9800 .
C2 C3 1.412(2) .
C2 H2 0.9300 .
C8 C7 1.370(2) .
C8 H8 0.9300 .
C3 H3 0.9300 .
C5 C6 1.361(3) .
C5 H5 0.9300 .
C7 C6 1.408(2) .
C7 H7 0.9300 .
C18 H18A 0.9600 .
C18 H18C 0.9600 .
C18 H18B 0.9600 .
C6 H6 0.9300 .
C19 H19A 0.9600 .
C19 H19C 0.9600 .
C19 H19B 0.9600 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C25 C25 C26 O28 5.9(3) 2_646 .
C25 C25 C26 O27 -174.17(17) 2_646 .
O22 C23 C24 C24 -2.1(3) . 2_645
O21 C23 C24 C24 177.71(19) . 2_645
C17 N16 C14 C13 178.23(11) . .
C12 O11 C1 C2 3.29(19) . .
C12 O11 C1 C9 -176.61(11) . .
C8 C9 C1 O11 0.21(18) . .
C10 C9 C1 O11 -179.78(11) . .
C8 C9 C1 C2 -179.69(13) . .
C10 C9 C1 C2 0.32(19) . .
C1 O11 C12 C13 179.25(11) . .
C14 N16 C17 C19 71.55(17) . .
C14 N16 C17 C18 -163.64(13) . .
C8 C9 C10 C4 -178.53(12) . .
C1 C9 C10 C4 1.46(18) . .
C8 C9 C10 C5 1.90(19) . .
C1 C9 C10 C5 -178.11(12) . .
C9 C10 C4 C3 -2.0(2) . .
C5 C10 C4 C3 177.58(13) . .
O11 C12 C13 O15 67.87(14) . .
O11 C12 C13 C14 -56.62(13) . .
N16 C14 C13 O15 49.71(14) . .
N16 C14 C13 C12 174.18(10) . .
O11 C1 C2 C3 178.52(13) . .
C9 C1 C2 C3 -1.6(2) . .
C10 C9 C8 C7 -1.0(2) . .
C1 C9 C8 C7 178.96(13) . .
C10 C4 C3 C2 0.7(2) . .
C1 C2 C3 C4 1.1(2) . .
C4 C10 C5 C6 179.43(15) . .
C9 C10 C5 C6 -1.0(2) . .
C9 C8 C7 C6 -0.7(2) . .
C10 C5 C6 C7 -0.7(2) . .
C8 C7 C6 C5 1.6(3) . .
