# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_pro-fum-1-1
_database_code_depnum_ccdc_archive 'CCDC 1407007'
_audit_update_record             
;
2015-06-16 deposited with the CCDC.
2015-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'Propranolol fumarate (1:1)'
_chemical_melting_point          ?
_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

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6157(2)
_cell_length_b                   9.9155(2)
_cell_length_c                   13.1345(4)
_cell_angle_alpha                97.3910(10)
_cell_angle_beta                 102.2400(10)
_cell_angle_gamma                109.8990(10)
_cell_volume                     1006.17(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6761
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6668
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0356
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         27.45
_reflns_number_total             4597
_reflns_number_gt                3915
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_cell_refinement       'HKL Scalepack (Otwinovski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinovski & Minor, 1997)'
_computing_structure_solution    'SIR2011 (Burla, 2012)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  
;
SHELXL-97 (Sheldrick, 2008), 
PLATON (Spek, 2009) and publCIF (Westrip, 2010)
;

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0556P)²+0.3863P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4597
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1273
_refine_ls_wR_factor_gt          0.1207
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
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 . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
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) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.463
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.039
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_pro-fum-2-1
_database_code_depnum_ccdc_archive 'CCDC 1407008'
_audit_update_record             
;
2015-06-16 deposited with the CCDC.
2015-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'Propranolol fumarate (2:1)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H22 N O2, 0.5(C4 H2 O4)'
_chemical_formula_sum            'C18 H23 N O4'
_chemical_formula_weight         317.37

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7989(3)
_cell_length_b                   9.1669(4)
_cell_length_c                   12.4724(6)
_cell_angle_alpha                89.470(2)
_cell_angle_beta                 75.754(2)
_cell_angle_gamma                76.412(3)
_cell_volume                     838.95(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7993
_cell_measurement_theta_min      0.9
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            'Colourless '
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5428
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         27.53
_reflns_number_total             3805
_reflns_number_gt                3006
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_cell_refinement       'HKL Scalepack (Otwinovski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinovski & Minor, 1997)'
_computing_structure_solution    'SIR2011 (Burla, 2012)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  
;
SHELXL-97 (Sheldrick, 2008), 
PLATON (Spek, 2009) and publCIF (Westrip, 2010)
;

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0399P)²+0.3344P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3805
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1255
_refine_ls_wR_factor_gt          0.1150
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.4132(2) 1.04192(19) 0.86501(12) 0.0325(3) Uani 1 1 d . . .
C2 C 0.3086(2) 0.9676(2) 0.93912(14) 0.0432(4) Uani 1 1 d . . .
H2 H 0.3211 0.8651 0.9277 0.052 Uiso 1 1 calc R . .
C3 C 0.1811(2) 1.0471(2) 1.03341(15) 0.0481(5) Uani 1 1 d . . .
H3 H 0.1118 0.9955 1.0844 0.058 Uiso 1 1 calc R . .
C4 C 0.1580(2) 1.1965(2) 1.05087(14) 0.0440(4) Uani 1 1 d . . .
H4 H 0.0720 1.2470 1.1127 0.053 Uiso 1 1 calc R . .
C5 C 0.2461(3) 1.4317(2) 0.99050(18) 0.0598(6) Uani 1 1 d . . .
H5 H 0.1599 1.4850 1.0511 0.072 Uiso 1 1 calc R . .
C6 C 0.3531(4) 1.5042(3) 0.9175(2) 0.0792(8) Uani 1 1 d . . .
H6 H 0.3400 1.6067 0.9293 0.095 Uiso 1 1 calc R . .
C7 C 0.4826(3) 1.4276(2) 0.8250(2) 0.0654(6) Uani 1 1 d . . .
H7 H 0.5540 1.4795 0.7756 0.078 Uiso 1 1 calc R . .
C8 C 0.5046(2) 1.2774(2) 0.80668(15) 0.0421(4) Uani 1 1 d . . .
H8 H 0.5914 1.2268 0.7452 0.051 Uiso 1 1 calc R . .
C9 C 0.3958(2) 1.19854(18) 0.88092(13) 0.0323(3) Uani 1 1 d . . .
C10 C 0.2647(2) 1.2762(2) 0.97505(14) 0.0385(4) Uani 1 1 d . . .
O11 O 0.53914(15) 0.97560(13) 0.77034(9) 0.0367(3) Uani 1 1 d . . .
C12 C 0.5706(2) 0.81686(19) 0.75479(14) 0.0378(4) Uani 1 1 d . . .
H12A H 0.4638 0.7912 0.7410 0.045 Uiso 1 1 calc R . .
H12B H 0.5951 0.7684 0.8207 0.045 Uiso 1 1 calc R . .
C13 C 0.7330(2) 0.7641(2) 0.65653(13) 0.0411(4) Uani 1 1 d . . .
H13 H 0.8335 0.8022 0.6741 0.049 Uiso 0.50 1 d PR . .
H13' H 0.7335 0.6568 0.6422 0.049 Uiso 0.50 1 d PR . .
C14 C 0.70276(19) 0.83826(17) 0.55200(12) 0.0307(3) Uani 1 1 d . . .
H14A H 0.5835 0.8346 0.5436 0.037 Uiso 1 1 calc R . .
H14B H 0.7066 0.9429 0.5570 0.037 Uiso 1 1 calc R . .
N16 N 0.84587(16) 0.76026(15) 0.45386(10) 0.0272(3) Uani 1 1 d . . .
H16A H 0.837(2) 0.660(2) 0.4511(14) 0.038(5) Uiso 1 1 d . . .
H16B H 0.966(3) 0.758(2) 0.4652(15) 0.042(5) Uiso 1 1 d . . .
C17 C 0.8335(2) 0.82706(17) 0.34424(12) 0.0300(3) Uani 1 1 d . . .
H17 H 0.7076 0.8432 0.3380 0.036 Uiso 1 1 calc R . .
C18 C 0.9569(2) 0.7149(2) 0.25257(13) 0.0388(4) Uani 1 1 d . . .
H18B H 0.9199 0.6218 0.2597 0.058 Uiso 1 1 calc R . .
H18A H 1.0805 0.6980 0.2582 0.058 Uiso 1 1 calc R . .
H18C H 0.9482 0.7541 0.1819 0.058 Uiso 1 1 calc R . .
C19 C 0.8851(3) 0.9764(2) 0.33775(15) 0.0442(4) Uani 1 1 d . . .
H19C H 0.8042 1.0439 0.3969 0.066 Uiso 1 1 calc R . .
H19B H 0.8758 1.0182 0.2680 0.066 Uiso 1 1 calc R . .
H19A H 1.0081 0.9619 0.3442 0.066 Uiso 1 1 calc R . .
C23 C 0.5412(2) 0.44467(17) 0.52562(14) 0.0332(3) Uani 1 1 d . . .
H23 H 0.4718 0.3897 0.5840 0.040 Uiso 1 1 d R . .
C22 C 0.7441(2) 0.38363(17) 0.49703(14) 0.0327(4) Uani 1 1 d . . .
O20 O 0.80236(15) 0.26279(13) 0.53866(11) 0.0422(3) Uani 1 1 d . . .
O21 O 0.84243(14) 0.45615(12) 0.43321(10) 0.0375(3) Uani 1 1 d . . .
O15 O 0.7884(3) 0.6188(2) 0.65425(18) 0.0327(5) Uani 0.50 1 d P . .
H15 H 0.9183 0.5875 0.6239 0.039 Uiso 0.50 1 d PR . .
O15' O 0.8836(3) 0.7543(3) 0.68325(18) 0.0390(5) Uani 0.50 1 d P . .
H15' H 0.9777 0.6923 0.6364 0.047 Uiso 0.50 1 d PR . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.365(2) . ?
C1 O11 1.3749(18) . ?
C1 C9 1.421(2) . ?
C2 C3 1.416(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.351(3) . ?
C3 H3 0.9300 . ?
C4 C10 1.416(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.358(3) . ?
C5 C10 1.409(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.398(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.361(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.410(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.419(2) . ?
O11 C12 1.424(2) . ?
C12 C13 1.516(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O15' 1.282(3) . ?
C13 O15 1.298(3) . ?
C13 C14 1.509(2) . ?
C13 H13 0.9999 . ?
C13 H13' 1.0001 . ?
C14 N16 1.4914(18) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
N16 C17 1.5084(19) . ?
N16 H16A 0.941(19) . ?
N16 H16B 0.977(19) . ?
C17 C19 1.511(2) . ?
C17 C18 1.518(2) . ?
C17 H17 0.9800 . ?
C18 H18B 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19C 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19A 0.9600 . ?
C23 C23 1.317(3) 2_666 ?
C23 C22 1.501(2) . ?
C23 H23 1.0020 . ?
C22 O20 1.2539(19) . ?
C22 O21 1.262(2) . ?
O15 O15' 1.673(3) . ?
O15 H13' 0.5367 . ?
O15 H15 0.9634 . ?
O15' H13 0.5468 . ?
O15' H15' 0.8955 . ?

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
_geom_angle_publ_flag
C2 C1 O11 124.26(15) . . ?
C2 C1 C9 120.94(15) . . ?
O11 C1 C9 114.79(13) . . ?
C1 C2 C3 119.71(17) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 121.32(17) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C10 120.03(16) . . ?
C3 C4 H4 120.0 . . ?
C10 C4 H4 120.0 . . ?
C6 C5 C10 120.45(19) . . ?
C6 C5 H5 119.8 . . ?
C10 C5 H5 119.8 . . ?
C5 C6 C7 121.2(2) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 120.3(2) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 120.03(17) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C10 119.71(16) . . ?
C8 C9 C1 122.05(14) . . ?
C10 C9 C1 118.23(15) . . ?
C5 C10 C4 121.91(17) . . ?
C5 C10 C9 118.34(17) . . ?
C4 C10 C9 119.75(16) . . ?
C1 O11 C12 116.79(12) . . ?
O11 C12 C13 108.20(13) . . ?
O11 C12 H12A 110.1 . . ?
C13 C12 H12A 110.1 . . ?
O11 C12 H12B 110.1 . . ?
C13 C12 H12B 110.1 . . ?
H12A C12 H12B 108.4 . . ?
O15' C13 O15 80.87(17) . . ?
O15' C13 C14 120.19(18) . . ?
O15 C13 C14 118.97(17) . . ?
O15' C13 C12 111.48(17) . . ?
O15 C13 C12 109.52(16) . . ?
C14 C13 C12 112.14(13) . . ?
O15' C13 H13 23.9 . . ?
O15 C13 H13 104.6 . . ?
C14 C13 H13 105.1 . . ?
C12 C13 H13 105.2 . . ?
O15' C13 H13' 103.2 . . ?
O15 C13 H13' 22.6 . . ?
C14 C13 H13' 103.9 . . ?
C12 C13 H13' 103.8 . . ?
H13 C13 H13' 126.7 . . ?
N16 C14 C13 110.24(12) . . ?
N16 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
N16 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C14 N16 C17 115.27(11) . . ?
C14 N16 H16A 107.3(11) . . ?
C17 N16 H16A 109.2(11) . . ?
C14 N16 H16B 109.2(11) . . ?
C17 N16 H16B 108.8(11) . . ?
H16A N16 H16B 106.7(15) . . ?
N16 C17 C19 110.15(12) . . ?
N16 C17 C18 108.12(12) . . ?
C19 C17 C18 112.04(14) . . ?
N16 C17 H17 108.8 . . ?
C19 C17 H17 108.8 . . ?
C18 C17 H17 108.8 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18A 109.5 . . ?
H18B C18 H18A 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
C17 C19 H19C 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19C C19 H19B 109.5 . . ?
C17 C19 H19A 109.5 . . ?
H19C C19 H19A 109.5 . . ?
H19B C19 H19A 109.5 . . ?
C23 C23 C22 123.4(2) 2_666 . ?
C23 C23 H23 122.2 2_666 . ?
C22 C23 H23 114.4 . . ?
O20 C22 O21 125.06(14) . . ?
O20 C22 C23 116.69(14) . . ?
O21 C22 C23 118.24(13) . . ?
C13 O15 O15' 49.14(13) . . ?
C13 O15 H13' 45.7 . . ?
O15' O15 H13' 94.5 . . ?
C13 O15 H15 110.7 . . ?
O15' O15 H15 71.2 . . ?
H13' O15 H15 134.7 . . ?
C13 O15' O15 49.99(13) . . ?
C13 O15' H13 47.8 . . ?
O15 O15' H13 97.6 . . ?
C13 O15' H15' 112.3 . . ?
O15 O15' H15' 78.1 . . ?
H13 O15' H15' 129.0 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 C1 C2 C3 -179.17(15) . . . . ?
C9 C1 C2 C3 -0.1(3) . . . . ?
C1 C2 C3 C4 1.2(3) . . . . ?
C2 C3 C4 C10 -1.1(3) . . . . ?
C10 C5 C6 C7 0.7(4) . . . . ?
C5 C6 C7 C8 -0.4(4) . . . . ?
C6 C7 C8 C9 0.4(3) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C7 C8 C9 C1 179.69(18) . . . . ?
C2 C1 C9 C8 178.80(16) . . . . ?
O11 C1 C9 C8 -2.1(2) . . . . ?
C2 C1 C9 C10 -1.0(2) . . . . ?
O11 C1 C9 C10 178.15(13) . . . . ?
C6 C5 C10 C4 178.6(2) . . . . ?
C6 C5 C10 C9 -0.8(3) . . . . ?
C3 C4 C10 C5 -179.50(18) . . . . ?
C3 C4 C10 C9 -0.1(3) . . . . ?
C8 C9 C10 C5 0.8(2) . . . . ?
C1 C9 C10 C5 -179.47(16) . . . . ?
C8 C9 C10 C4 -178.71(15) . . . . ?
C1 C9 C10 C4 1.1(2) . . . . ?
C2 C1 O11 C12 -5.2(2) . . . . ?
C9 C1 O11 C12 175.71(13) . . . . ?
C1 O11 C12 C13 -171.20(13) . . . . ?
O11 C12 C13 O15' 79.2(2) . . . . ?
O11 C12 C13 O15 166.83(16) . . . . ?
O11 C12 C13 C14 -58.82(19) . . . . ?
O15' C13 C14 N16 58.3(2) . . . . ?
O15 C13 C14 N16 -38.2(2) . . . . ?
C12 C13 C14 N16 -167.78(14) . . . . ?
C13 C14 N16 C17 -178.33(13) . . . . ?
C14 N16 C17 C19 70.81(16) . . . . ?
C14 N16 C17 C18 -166.46(13) . . . . ?
C23 C23 C22 O20 -168.26(19) 2_666 . . . ?
C23 C23 C22 O21 11.4(3) 2_666 . . . ?
C14 C13 O15 O15' 119.5(2) . . . . ?
C12 C13 O15 O15' -109.66(19) . . . . ?
C14 C13 O15' O15 -118.3(2) . . . . ?
C12 C13 O15' O15 107.48(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.037
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_pro-male-1-1
_database_code_depnum_ccdc_archive 'CCDC 1407009'
_audit_update_record             
;
2015-06-16 deposited with the CCDC.
2015-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'Propranolol maleate (1:1)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H22 N O2, C4 H3 O4'
_chemical_formula_sum            'C20 H25 N O6'
_chemical_formula_weight         375.41

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.2010(3)
_cell_length_b                   8.7153(3)
_cell_length_c                   24.7710(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.6180(10)
_cell_angle_gamma                90.00
_cell_volume                     1979.93(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11927
_diffrn_reflns_av_R_equivalents  0.1475
_diffrn_reflns_av_sigmaI/netI    0.2099
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         27.60
_reflns_number_total             4491
_reflns_number_gt                1813
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_cell_refinement       'HKL Scalepack (Otwinovski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinovski & Minor, 1997)'
_computing_structure_solution    'SIR2011 (Burla, 2012)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  
;
SHELXL-97 (Sheldrick, 2008), 
PLATON (Spek, 2009) and publCIF (Westrip, 2010)
;

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0459P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4491
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2376
_refine_ls_R_factor_gt           0.0826
_refine_ls_wR_factor_ref         0.1528
_refine_ls_wR_factor_gt          0.1179
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_restrained_S_all      0.980
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O11 O 0.3214(2) 0.0712(2) 0.08706(10) 0.0344(6) Uani 1 1 d . . .
O20 O 0.8207(3) 0.5046(3) 0.17480(12) 0.0546(8) Uani 1 1 d . . .
H20 H 0.705(5) 0.517(5) 0.1709(19) 0.110(17) Uiso 1 1 d . . .
O15 O 0.1373(2) 0.1898(3) 0.16726(11) 0.0393(7) Uani 1 1 d . . .
H15 H 0.140(4) 0.152(4) 0.2048(18) 0.081(14) Uiso 1 1 d . . .
N16 N 0.1922(3) 0.5097(3) 0.14558(13) 0.0321(7) Uani 1 1 d . . .
H16B H 0.105(3) 0.488(3) 0.1591(14) 0.046(10) Uiso 1 1 d . . .
H16A H 0.260(3) 0.538(3) 0.1756(14) 0.032(10) Uiso 1 1 d . . .
O26 O 0.3936(2) 0.5865(3) 0.23046(10) 0.0514(7) Uani 1 1 d . . .
C10 C 0.3935(3) -0.2324(3) -0.00981(15) 0.0321(9) Uani 1 1 d . . .
C9 C 0.3278(3) -0.1053(3) 0.01509(15) 0.0316(9) Uani 1 1 d . . .
C14 C 0.2572(3) 0.3762(3) 0.11910(14) 0.0334(9) Uani 1 1 d . . .
H14A H 0.3503 0.4053 0.1063 0.040 Uiso 1 1 calc R . .
H14B H 0.1934 0.3438 0.0881 0.040 Uiso 1 1 calc R . .
O27 O 0.5576(3) 0.5158(3) 0.17478(11) 0.0554(7) Uani 1 1 d . . .
C1 C 0.3938(3) -0.0494(3) 0.06514(14) 0.0300(8) Uani 1 1 d . . .
C8 C 0.1980(3) -0.0419(4) -0.01023(15) 0.0348(9) Uani 1 1 d . . .
H8 H 0.1550 0.0416 0.0056 0.042 Uiso 1 1 calc R . .
O21 O 1.0071(3) 0.5378(3) 0.23441(12) 0.0708(9) Uani 1 1 d . . .
C2 C 0.5184(3) -0.1143(3) 0.08895(15) 0.0358(9) Uani 1 1 d . . .
H2 H 0.5603 -0.0770 0.1218 0.043 Uiso 1 1 calc R . .
C6 C 0.1992(4) -0.2289(4) -0.08183(16) 0.0437(10) Uani 1 1 d . . .
H6 H 0.1559 -0.2703 -0.1138 0.052 Uiso 1 1 calc R . .
C13 C 0.2791(3) 0.2446(3) 0.15914(14) 0.0324(9) Uani 1 1 d . . .
H13 H 0.3233 0.2851 0.1935 0.039 Uiso 1 1 calc R . .
C3 C 0.5825(3) -0.2385(4) 0.06311(16) 0.0400(10) Uani 1 1 d . . .
H3 H 0.6669 -0.2828 0.0794 0.048 Uiso 1 1 calc R . .
C5 C 0.3244(4) -0.2908(4) -0.05841(15) 0.0392(10) Uani 1 1 d . . .
H5 H 0.3657 -0.3742 -0.0749 0.047 Uiso 1 1 calc R . .
C7 C 0.1346(4) -0.1018(4) -0.05773(16) 0.0413(10) Uani 1 1 d . . .
H7 H 0.0495 -0.0588 -0.0739 0.050 Uiso 1 1 calc R . .
C4 C 0.5243(4) -0.2950(4) 0.01528(16) 0.0398(10) Uani 1 1 d . . .
H4 H 0.5703 -0.3753 -0.0012 0.048 Uiso 1 1 calc R . .
C12 C 0.3773(3) 0.1219(4) 0.13949(14) 0.0337(9) Uani 1 1 d . . .
H12A H 0.4750 0.1624 0.1377 0.040 Uiso 1 1 calc R . .
H12B H 0.3822 0.0362 0.1645 0.040 Uiso 1 1 calc R . .
C17 C 0.1666(4) 0.6489(4) 0.11039(16) 0.0414(10) Uani 1 1 d . . .
H17 H 0.2584 0.6745 0.0950 0.050 Uiso 1 1 calc R . .
C22 C 0.8772(4) 0.5488(4) 0.22126(19) 0.0507(11) Uani 1 1 d . . .
C25 C 0.5223(4) 0.5738(4) 0.21881(17) 0.0455(10) Uani 1 1 d . . .
C19 C 0.1256(4) 0.7816(4) 0.14535(17) 0.0590(12) Uani 1 1 d . . .
H19A H 0.2015 0.7981 0.1737 0.088 Uiso 1 1 calc R . .
H19C H 0.0360 0.7585 0.1610 0.088 Uiso 1 1 calc R . .
H19B H 0.1133 0.8725 0.1236 0.088 Uiso 1 1 calc R . .
C24 C 0.6378(4) 0.6291(5) 0.25932(18) 0.0752(15) Uani 1 1 d . . .
H24 H 0.6033 0.6791 0.2889 0.090 Uiso 1 1 calc R . .
C23 C 0.7827(4) 0.6196(6) 0.26056(19) 0.0815(16) Uani 1 1 d . . .
H23 H 0.8326 0.6643 0.2907 0.098 Uiso 1 1 calc R . .
C18 C 0.0534(4) 0.6164(4) 0.06407(18) 0.0650(13) Uani 1 1 d . . .
H18C H 0.0852 0.5321 0.0431 0.097 Uiso 1 1 calc R . .
H18B H 0.0408 0.7058 0.0415 0.097 Uiso 1 1 calc R . .
H18A H -0.0376 0.5908 0.0783 0.097 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O11 C1 1.379(3) . ?
O11 C12 1.428(4) . ?
O20 C22 1.283(5) . ?
O20 H20 1.06(5) . ?
O15 C13 1.418(3) . ?
O15 H15 0.98(4) . ?
N16 C14 1.485(4) . ?
N16 C17 1.501(4) . ?
N16 H16B 0.92(3) . ?
N16 H16A 0.96(3) . ?
O26 C25 1.245(4) . ?
C10 C5 1.410(5) . ?
C10 C4 1.418(5) . ?
C10 C9 1.426(4) . ?
C9 C8 1.416(4) . ?
C9 C1 1.422(5) . ?
C14 C13 1.519(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
O27 C25 1.268(4) . ?
O27 H20 1.37(5) . ?
C1 C2 1.369(4) . ?
C8 C7 1.373(5) . ?
C8 H8 0.9300 . ?
O21 C22 1.217(4) . ?
C2 C3 1.411(4) . ?
C2 H2 0.9300 . ?
C6 C5 1.360(5) . ?
C6 C7 1.412(4) . ?
C6 H6 0.9300 . ?
C13 C12 1.505(4) . ?
C13 H13 0.9800 . ?
C3 C4 1.353(5) . ?
C3 H3 0.9300 . ?
C5 H5 0.9300 . ?
C7 H7 0.9300 . ?
C4 H4 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C17 C19 1.511(5) . ?
C17 C18 1.513(5) . ?
C17 H17 0.9800 . ?
C22 C23 1.491(5) . ?
C25 C24 1.483(5) . ?
C19 H19A 0.9600 . ?
C19 H19C 0.9600 . ?
C19 H19B 0.9600 . ?
C24 C23 1.333(5) . ?
C24 H24 0.9300 . ?
C23 H23 0.9300 . ?
C18 H18C 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18A 0.9600 . ?

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
_geom_angle_publ_flag
C1 O11 C12 116.4(2) . . ?
C22 O20 H20 112(2) . . ?
C13 O15 H15 107(2) . . ?
C14 N16 C17 115.2(3) . . ?
C14 N16 H16B 113.6(19) . . ?
C17 N16 H16B 106(2) . . ?
C14 N16 H16A 106.3(17) . . ?
C17 N16 H16A 107.8(17) . . ?
H16B N16 H16A 108(3) . . ?
C5 C10 C4 122.9(3) . . ?
C5 C10 C9 118.2(3) . . ?
C4 C10 C9 118.9(3) . . ?
C8 C9 C1 122.6(3) . . ?
C8 C9 C10 118.9(3) . . ?
C1 C9 C10 118.5(3) . . ?
N16 C14 C13 109.9(3) . . ?
N16 C14 H14A 109.7 . . ?
C13 C14 H14A 109.7 . . ?
N16 C14 H14B 109.7 . . ?
C13 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C25 O27 H20 112.4(19) . . ?
C2 C1 O11 124.0(3) . . ?
C2 C1 C9 121.2(3) . . ?
O11 C1 C9 114.7(3) . . ?
C7 C8 C9 121.1(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C1 C2 C3 119.2(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C5 C6 C7 120.1(4) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
O15 C13 C12 112.9(2) . . ?
O15 C13 C14 105.8(3) . . ?
C12 C13 C14 112.1(3) . . ?
O15 C13 H13 108.6 . . ?
C12 C13 H13 108.6 . . ?
C14 C13 H13 108.6 . . ?
C4 C3 C2 121.8(3) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C6 C5 C10 121.9(3) . . ?
C6 C5 H5 119.0 . . ?
C10 C5 H5 119.0 . . ?
C8 C7 C6 119.7(3) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C3 C4 C10 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C10 C4 H4 119.8 . . ?
O11 C12 C13 109.4(3) . . ?
O11 C12 H12A 109.8 . . ?
C13 C12 H12A 109.8 . . ?
O11 C12 H12B 109.8 . . ?
C13 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
N16 C17 C19 108.7(3) . . ?
N16 C17 C18 110.8(3) . . ?
C19 C17 C18 112.9(3) . . ?
N16 C17 H17 108.1 . . ?
C19 C17 H17 108.1 . . ?
C18 C17 H17 108.1 . . ?
O21 C22 O20 122.3(4) . . ?
O21 C22 C23 118.0(4) . . ?
O20 C22 C23 119.6(3) . . ?
O26 C25 O27 123.3(4) . . ?
O26 C25 C24 117.2(3) . . ?
O27 C25 C24 119.5(3) . . ?
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 . . ?
C23 C24 C25 131.0(4) . . ?
C23 C24 H24 114.5 . . ?
C25 C24 H24 114.5 . . ?
C24 C23 C22 130.2(4) . . ?
C24 C23 H23 114.9 . . ?
C22 C23 H23 114.9 . . ?
C17 C18 H18C 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18C C18 H18B 109.5 . . ?
C17 C18 H18A 109.5 . . ?
H18C C18 H18A 109.5 . . ?
H18B C18 H18A 109.5 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 C10 C9 C8 -0.9(4) . . . . ?
C4 C10 C9 C8 179.4(3) . . . . ?
C5 C10 C9 C1 177.7(3) . . . . ?
C4 C10 C9 C1 -2.0(4) . . . . ?
C17 N16 C14 C13 179.3(3) . . . . ?
C12 O11 C1 C2 -4.3(4) . . . . ?
C12 O11 C1 C9 174.9(3) . . . . ?
C8 C9 C1 C2 179.2(3) . . . . ?
C10 C9 C1 C2 0.7(4) . . . . ?
C8 C9 C1 O11 0.0(4) . . . . ?
C10 C9 C1 O11 -178.5(2) . . . . ?
C1 C9 C8 C7 -177.9(3) . . . . ?
C10 C9 C8 C7 0.6(4) . . . . ?
O11 C1 C2 C3 179.3(3) . . . . ?
C9 C1 C2 C3 0.2(4) . . . . ?
N16 C14 C13 O15 70.7(3) . . . . ?
N16 C14 C13 C12 -165.9(3) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C7 C6 C5 C10 0.3(5) . . . . ?
C4 C10 C5 C6 -179.8(3) . . . . ?
C9 C10 C5 C6 0.5(5) . . . . ?
C9 C8 C7 C6 0.2(5) . . . . ?
C5 C6 C7 C8 -0.6(5) . . . . ?
C2 C3 C4 C10 -1.6(5) . . . . ?
C5 C10 C4 C3 -177.2(3) . . . . ?
C9 C10 C4 C3 2.5(5) . . . . ?
C1 O11 C12 C13 -175.4(2) . . . . ?
O15 C13 C12 O11 64.6(4) . . . . ?
C14 C13 C12 O11 -54.7(3) . . . . ?
C14 N16 C17 C19 -170.2(3) . . . . ?
C14 N16 C17 C18 65.1(4) . . . . ?
O26 C25 C24 C23 173.7(5) . . . . ?
O27 C25 C24 C23 -5.9(7) . . . . ?
C25 C24 C23 C22 -0.3(9) . . . . ?
O21 C22 C23 C24 -171.1(5) . . . . ?
O20 C22 C23 C24 10.3(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.98
_diffrn_reflns_theta_full        27.60
_diffrn_measured_fraction_theta_full 0.98
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.047
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1407010'
_audit_update_record             
;
2015-06-16 deposited with the CCDC.
2015-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H22 N O4'
_chemical_formula_weight         304.36

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.1696(3)
_cell_length_b                   5.6053(2)
_cell_length_c                   18.9321(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.820(2)
_cell_angle_gamma                90.00
_cell_volume                     856.71(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             326
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4766
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.4914
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         32.03
_reflns_number_total             4766
_reflns_number_gt                1267
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0169P)²+0.5239P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_number_reflns         4766
_refine_ls_number_parameters     244
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1305
_refine_ls_R_factor_gt           0.0044
_refine_ls_wR_factor_ref         0.0157
_refine_ls_wR_factor_gt          0.0054
_refine_ls_goodness_of_fit_ref   0.092
_refine_ls_restrained_S_all      0.092
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
C1 C 0.19307(7) -0.07697(10) 0.35918(3) 0.02522(12) Uani 1 1 d . . .
C2 C 0.34832(7) -0.11865(9) 0.39567(3) 0.02972(13) Uani 1 1 d . . .
H2 H 0.4363 -0.0206 0.3888 0.036 Uiso 1 1 calc R . .
C3 C 0.37368(8) -0.31276(11) 0.44409(3) 0.03563(14) Uani 1 1 d . . .
H3 H 0.4791 -0.3409 0.4690 0.043 Uiso 1 1 calc R . .
C4 C 0.24686(8) -0.45868(11) 0.45483(3) 0.03751(15) Uani 1 1 d . . .
H4 H 0.2664 -0.5856 0.4866 0.045 Uiso 1 1 calc R . .
C5 C -0.05102(9) -0.56696(11) 0.42730(4) 0.04417(17) Uani 1 1 d . . .
H5 H -0.0339 -0.6988 0.4574 0.053 Uiso 1 1 calc R . .
C6 C -0.20550(9) -0.51832(13) 0.39295(4) 0.0511(2) Uani 1 1 d . . .
H6 H -0.2930 -0.6173 0.4000 0.061 Uiso 1 1 calc R . .
C7 C -0.23548(8) -0.32390(13) 0.34762(4) 0.04709(19) Uani 1 1 d . . .
H7 H -0.3427 -0.2935 0.3250 0.057 Uiso 1 1 calc R . .
C8 C -0.10840(7) -0.17528(13) 0.33575(3) 0.03744(14) Uani 1 1 d . . .
H8 H -0.1294 -0.0452 0.3052 0.045 Uiso 1 1 calc R . .
C9 C 0.05572(6) -0.22239(10) 0.37064(3) 0.02670(12) Uani 1 1 d . . .
C10 C 0.08513(7) -0.41832(10) 0.41780(3) 0.03313(14) Uani 1 1 d . . .
O11 O 0.15270(4) 0.09811(7) 0.30920(2) 0.03214(10) Uani 1 1 d . . .
C12 C 0.28198(6) 0.24115(11) 0.28863(3) 0.02680(11) Uani 1 1 d . . .
H12B H 0.3716 0.1412 0.2776 0.032 Uiso 1 1 calc R . .
H12A H 0.3255 0.3493 0.3269 0.032 Uiso 1 1 calc R . .
C13 C 0.20569(6) 0.38029(9) 0.22290(3) 0.02112(11) Uani 1 1 d . . .
H13 H 0.1137 0.4788 0.2338 0.025 Uiso 1 1 calc R . .
C14 C 0.34188(5) 0.53630(9) 0.20183(3) 0.02063(10) Uani 1 1 d . . .
H14A H 0.3962 0.6170 0.2444 0.025 Uiso 1 1 calc R . .
H14B H 0.4234 0.4334 0.1851 0.025 Uiso 1 1 calc R . .
O15 O 0.14923(4) 0.21764(7) 0.16625(2) 0.02280(8) Uani 1 1 d . . .
H15 H 0.0414(8) 0.1820(13) 0.1658(4) 0.068(2) Uiso 1 1 d . . .
N16 N 0.29026(5) 0.72095(8) 0.14555(2) 0.02018(9) Uani 1 1 d . . .
H16A H 0.2113(5) 0.8179(8) 0.1595(3) 0.0121(12) Uiso 1 1 d . . .
H16B H 0.3872(7) 0.8285(10) 0.1430(3) 0.0418(18) Uiso 1 1 d . . .
C17 C 0.22725(6) 0.63516(8) 0.07040(3) 0.02093(10) Uani 1 1 d . . .
H17 H 0.1306 0.5325 0.0715 0.025 Uiso 1 1 calc R . .
C18 C 0.17455(7) 0.85328(10) 0.02436(3) 0.03261(13) Uani 1 1 d . . .
H18C H 0.0933 0.9419 0.0451 0.049 Uiso 1 1 calc R . .
H18B H 0.1279 0.8028 -0.0229 0.049 Uiso 1 1 calc R . .
H18A H 0.2693 0.9525 0.0219 0.049 Uiso 1 1 calc R . .
C19 C 0.35990(7) 0.49414(11) 0.04073(3) 0.03385(13) Uani 1 1 d . . .
H19A H 0.4522 0.5964 0.0367 0.051 Uiso 1 1 calc R . .
H19C H 0.3154 0.4326 -0.0056 0.051 Uiso 1 1 calc R . .
H19B H 0.3960 0.3641 0.0723 0.051 Uiso 1 1 calc R . .
O20 O -0.31609(5) -0.38241(7) 0.16113(2) 0.03139(10) Uani 1 1 d . . .
H20 H -0.2626(9) -0.5298(15) 0.1612(4) 0.070(3) Uiso 1 1 d . . .
O21 O -0.06818(4) -0.23422(6) 0.14926(2) 0.03232(10) Uani 1 1 d . . .
C22 C -0.21165(6) -0.21103(8) 0.15620(3) 0.02002(10) Uani 1 1 d . . .
C23 C -0.29152(6) 0.03921(9) 0.16011(3) 0.02028(9) Uani 1 1 d . . .
O24 O -0.44257(4) 0.05235(6) 0.16065(2) 0.03044(10) Uani 1 1 d . . .
O25 O -0.19076(4) 0.20983(7) 0.16252(2) 0.02930(9) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O11 1.3681(6) . ?
C1 C2 1.3681(7) . ?
C1 C9 1.4301(7) . ?
C2 C3 1.4174(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.3595(8) . ?
C3 H3 0.9300 . ?
C4 C10 1.4158(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.3558(10) . ?
C5 C10 1.4230(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.3855(9) . ?
C6 H6 0.9300 . ?
C7 C8 1.3762(8) . ?
C7 H7 0.9300 . ?
C8 C9 1.4255(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.4125(7) . ?
O11 C12 1.4270(6) . ?
C12 C13 1.5189(7) . ?
C12 H12B 0.9700 . ?
C12 H12A 0.9700 . ?
C13 O15 1.4293(6) . ?
C13 C14 1.5159(7) . ?
C13 H13 0.9800 . ?
C14 N16 1.4989(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
O15 H15 0.902(7) . ?
N16 C17 1.5151(6) . ?
N16 H16A 0.913(5) . ?
N16 H16B 1.003(6) . ?
C17 C19 1.5170(7) . ?
C17 C18 1.5248(7) . ?
C17 H17 0.9800 . ?
C18 H18C 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18A 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19C 0.9600 . ?
C19 H19B 0.9600 . ?
O20 C22 1.2976(6) . ?
O20 H20 0.934(8) . ?
O21 C22 1.2063(5) . ?
C22 C23 1.5535(6) . ?
C23 O24 1.2378(5) . ?
C23 O25 1.2581(6) . ?

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
_geom_angle_publ_flag
O11 C1 C2 125.33(5) . . ?
O11 C1 C9 113.72(5) . . ?
C2 C1 C9 120.95(5) . . ?
C1 C2 C3 119.33(6) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 121.29(6) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C10 120.30(6) . . ?
C3 C4 H4 119.8 . . ?
C10 C4 H4 119.8 . . ?
C6 C5 C10 120.65(6) . . ?
C6 C5 H5 119.7 . . ?
C10 C5 H5 119.7 . . ?
C5 C6 C7 121.23(6) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 120.73(6) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 119.46(6) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C10 C9 C8 119.58(5) . . ?
C10 C9 C1 118.54(5) . . ?
C8 C9 C1 121.89(6) . . ?
C9 C10 C4 119.51(5) . . ?
C9 C10 C5 118.34(5) . . ?
C4 C10 C5 122.14(6) . . ?
C1 O11 C12 118.80(4) . . ?
O11 C12 C13 106.51(4) . . ?
O11 C12 H12B 110.4 . . ?
C13 C12 H12B 110.4 . . ?
O11 C12 H12A 110.4 . . ?
C13 C12 H12A 110.4 . . ?
H12B C12 H12A 108.6 . . ?
O15 C13 C14 109.63(4) . . ?
O15 C13 C12 109.38(4) . . ?
C14 C13 C12 106.64(4) . . ?
O15 C13 H13 110.4 . . ?
C14 C13 H13 110.4 . . ?
C12 C13 H13 110.4 . . ?
N16 C14 C13 116.59(4) . . ?
N16 C14 H14A 108.1 . . ?
C13 C14 H14A 108.1 . . ?
N16 C14 H14B 108.1 . . ?
C13 C14 H14B 108.1 . . ?
H14A C14 H14B 107.3 . . ?
C13 O15 H15 110.6(5) . . ?
C14 N16 C17 117.80(4) . . ?
C14 N16 H16A 109.9(3) . . ?
C17 N16 H16A 107.9(3) . . ?
C14 N16 H16B 108.2(4) . . ?
C17 N16 H16B 107.6(3) . . ?
H16A N16 H16B 104.7(4) . . ?
N16 C17 C19 110.73(4) . . ?
N16 C17 C18 107.93(4) . . ?
C19 C17 C18 111.18(5) . . ?
N16 C17 H17 109.0 . . ?
C19 C17 H17 109.0 . . ?
C18 C17 H17 109.0 . . ?
C17 C18 H18C 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18C C18 H18B 109.5 . . ?
C17 C18 H18A 109.5 . . ?
H18C C18 H18A 109.5 . . ?
H18B C18 H18A 109.5 . . ?
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 . . ?
C22 O20 H20 110.0(5) . . ?
O21 C22 O20 126.06(5) . . ?
O21 C22 C23 121.65(4) . . ?
O20 C22 C23 112.30(4) . . ?
O24 C23 O25 127.02(5) . . ?
O24 C23 C22 118.73(4) . . ?
O25 C23 C22 114.26(4) . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 C1 C2 C3 -177.53(6) . . . . ?
C9 C1 C2 C3 1.66(8) . . . . ?
C1 C2 C3 C4 0.19(9) . . . . ?
C2 C3 C4 C10 -0.39(10) . . . . ?
C10 C5 C6 C7 0.19(10) . . . . ?
C5 C6 C7 C8 0.50(11) . . . . ?
C6 C7 C8 C9 -0.04(10) . . . . ?
C7 C8 C9 C10 -1.09(9) . . . . ?
C7 C8 C9 C1 178.68(5) . . . . ?
O11 C1 C9 C10 176.03(5) . . . . ?
C2 C1 C9 C10 -3.25(8) . . . . ?
O11 C1 C9 C8 -3.75(8) . . . . ?
C2 C1 C9 C8 176.97(5) . . . . ?
C8 C9 C10 C4 -177.21(5) . . . . ?
C1 C9 C10 C4 3.00(8) . . . . ?
C8 C9 C10 C5 1.74(8) . . . . ?
C1 C9 C10 C5 -178.04(5) . . . . ?
C3 C4 C10 C9 -1.25(8) . . . . ?
C3 C4 C10 C5 179.84(6) . . . . ?
C6 C5 C10 C9 -1.31(9) . . . . ?
C6 C5 C10 C4 177.62(6) . . . . ?
C2 C1 O11 C12 4.68(8) . . . . ?
C9 C1 O11 C12 -174.56(5) . . . . ?
C1 O11 C12 C13 168.46(4) . . . . ?
O11 C12 C13 O15 -62.68(5) . . . . ?
O11 C12 C13 C14 178.85(4) . . . . ?
O15 C13 C14 N16 71.55(5) . . . . ?
C12 C13 C14 N16 -170.14(4) . . . . ?
C13 C14 N16 C17 -67.55(5) . . . . ?
C14 N16 C17 C19 -61.03(5) . . . . ?
C14 N16 C17 C18 177.08(4) . . . . ?
O21 C22 C23 O24 173.47(6) . . . . ?
O20 C22 C23 O24 -6.47(7) . . . . ?
O21 C22 C23 O25 -6.63(7) . . . . ?
O20 C22 C23 O25 173.43(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        32.03
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.027
_refine_diff_density_min         -0.079
_refine_diff_density_rms         0.007
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1407011'
_audit_update_record             
;
2015-06-16 deposited with the CCDC.
2015-11-01 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'Propranolol oxalate methanol solvate (2:1:1)'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C16 H22 N O2), C2 O4, 0.9(C H4 O)'
_chemical_formula_sum            'C34.90 H47.60 N2 O8.90'
_chemical_formula_weight         637.55

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b n 21'
_symmetry_space_group_name_Hall  'P 2c -2ab'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   10.7741(2)
_cell_length_b                   11.3507(2)
_cell_length_c                   28.2413(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3453.73(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    49344
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      32.032

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1368.8
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12030
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.2034
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         32.04
_reflns_number_total             12030
_reflns_number_gt                4389
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_cell_refinement       'HKL Scalepack (Otwinovski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinovski & Minor, 1997)'
_computing_structure_solution    'SIR2011 (Burla, 2012)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  
;
SHELXL-97 (Sheldrick, 2008), 
PLATON (Spek, 2009) and publCIF (Westrip, 2010)
;

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0546P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         12030
_refine_ls_number_parameters     423
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2359
_refine_ls_R_factor_gt           0.0792
_refine_ls_wR_factor_ref         0.1601
_refine_ls_wR_factor_gt          0.1215
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

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
O11 O 0.3203(2) 0.6872(2) 0.40627(10) 0.0362(6) Uani 1 1 d . . .
O15 O 0.4351(2) 0.8217(2) 0.33952(11) 0.0450(8) Uani 1 1 d . . .
H15 H 0.4801 0.8537 0.3200 0.068 Uiso 1 1 calc R . .
O11' O 0.31622(19) 0.7604(2) 0.14174(9) 0.0339(6) Uani 1 1 d . . .
N16 N 0.6946(2) 0.7555(2) 0.36095(10) 0.0258(7) Uani 1 1 d . . .
H16B H 0.6765 0.8316 0.3554 0.031 Uiso 1 1 calc R . .
H16A H 0.7147 0.7224 0.3330 0.031 Uiso 1 1 calc R . .
O21 O 0.7195(2) 1.0060(2) 0.33348(9) 0.0359(6) Uani 1 1 d . . .
C17 C 0.8056(3) 0.7498(3) 0.39290(14) 0.0305(9) Uani 1 1 d . . .
H17 H 0.8168 0.6682 0.4034 0.037 Uiso 1 1 calc R . .
O24 O 0.7638(2) 1.1836(2) 0.26875(9) 0.0324(6) Uani 1 1 d . . .
O15' O 0.4360(2) 0.8935(2) 0.20944(10) 0.0374(6) Uani 1 1 d . . .
H15' H 0.4888 0.9261 0.2257 0.056 Uiso 1 1 calc R . .
O25 O 0.7064(2) 1.05777(18) 0.21265(9) 0.0334(6) Uani 1 1 d . . .
O20 O 0.5884(2) 0.9292(2) 0.28089(9) 0.0358(6) Uani 1 1 d . . .
N16' N 0.6911(2) 0.8177(2) 0.18800(11) 0.0236(6) Uani 1 1 d . . .
16A' H 0.7106 0.7793 0.2149 0.028 Uiso 1 1 calc R . .
16B' H 0.6751 0.8931 0.1957 0.028 Uiso 1 1 calc R . .
C10 C 0.0607(3) 0.6707(3) 0.48937(14) 0.0306(9) Uani 1 1 d . . .
C10' C 0.0587(3) 0.7431(3) 0.05771(14) 0.0291(8) Uani 1 1 d . . .
C1' C 0.2094(3) 0.7179(3) 0.12214(14) 0.0282(8) Uani 1 1 d . . .
C13' C 0.4695(3) 0.7738(3) 0.20237(14) 0.0298(9) Uani 1 1 d . . .
H13' H 0.4954 0.7404 0.2328 0.036 Uiso 1 1 calc R . .
C9 C 0.1669(3) 0.7112(3) 0.46449(14) 0.0269(8) Uani 1 1 d . . .
C1 C 0.2112(3) 0.6453(3) 0.42561(13) 0.0280(8) Uani 1 1 d . . .
C23 C 0.7172(3) 1.0877(3) 0.25460(13) 0.0255(8) Uani 1 1 d . . .
C14 C 0.5812(3) 0.6959(3) 0.37972(13) 0.0266(8) Uani 1 1 d . . .
H14B H 0.5580 0.7320 0.4096 0.032 Uiso 1 1 calc R . .
H14A H 0.5999 0.6137 0.3858 0.032 Uiso 1 1 calc R . .
C13 C 0.4731(3) 0.7037(3) 0.34578(14) 0.0318(9) Uani 1 1 d . . .
H13 H 0.4988 0.6717 0.3151 0.038 Uiso 1 1 calc R . .
C8' C 0.2199(3) 0.8900(3) 0.06854(13) 0.0291(8) Uani 1 1 d . . .
H8' H 0.2879 0.9186 0.0853 0.035 Uiso 1 1 calc R . .
C22 C 0.6727(3) 1.0013(3) 0.29361(13) 0.0260(8) Uani 1 1 d . . .
C19 C 0.7849(4) 0.8264(3) 0.43577(14) 0.0413(10) Uani 1 1 d . . .
H19B H 0.7161 0.7964 0.4537 0.062 Uiso 1 1 calc R . .
H19C H 0.7672 0.9055 0.4258 0.062 Uiso 1 1 calc R . .
H19A H 0.8582 0.8261 0.4551 0.062 Uiso 1 1 calc R . .
C8 C 0.2227(3) 0.8197(3) 0.47890(14) 0.0334(9) Uani 1 1 d . . .
H8 H 0.2914 0.8482 0.4626 0.040 Uiso 1 1 calc R . .
C4' C -0.0018(3) 0.6404(3) 0.07415(15) 0.0374(10) Uani 1 1 d . . .
H4' H -0.0704 0.6115 0.0579 0.045 Uiso 1 1 calc R . .
C2' C 0.1461(3) 0.6205(3) 0.13774(14) 0.0335(9) Uani 1 1 d . . .
H2' H 0.1737 0.5793 0.1642 0.040 Uiso 1 1 calc R . .
C6 C 0.0734(4) 0.8405(3) 0.54189(14) 0.0415(10) Uani 1 1 d . . .
H6 H 0.0431 0.8826 0.5677 0.050 Uiso 1 1 calc R . .
C12' C 0.3564(3) 0.7068(3) 0.18490(14) 0.0340(9) Uani 1 1 d . . .
12B' H 0.3775 0.6248 0.1795 0.041 Uiso 1 1 calc R . .
12A' H 0.2907 0.7102 0.2083 0.041 Uiso 1 1 calc R . .
C17' C 0.8021(3) 0.8150(3) 0.15556(14) 0.0311(9) Uani 1 1 d . . .
H17' H 0.8121 0.7346 0.1435 0.037 Uiso 1 1 calc R . .
C7 C 0.1761(3) 0.8822(3) 0.51639(15) 0.0352(10) Uani 1 1 d . . .
H7 H 0.2130 0.9531 0.5250 0.042 Uiso 1 1 calc R . .
C9' C 0.1654(3) 0.7836(3) 0.08227(13) 0.0265(8) Uani 1 1 d . . .
C3' C 0.0391(3) 0.5836(3) 0.11340(15) 0.0374(10) Uani 1 1 d . . .
H3' H -0.0047 0.5187 0.1245 0.045 Uiso 1 1 calc R . .
C6' C 0.0731(3) 0.9105(3) 0.00542(14) 0.0364(9) Uani 1 1 d . . .
H6' H 0.0440 0.9525 -0.0206 0.044 Uiso 1 1 calc R . .
C18' C 0.7835(3) 0.8969(3) 0.11388(14) 0.0394(10) Uani 1 1 d . . .
18B' H 0.7685 0.9754 0.1252 0.059 Uiso 1 1 calc R . .
18C' H 0.7137 0.8708 0.0956 0.059 Uiso 1 1 calc R . .
18A' H 0.8566 0.8964 0.0944 0.059 Uiso 1 1 calc R . .
C7' C 0.1751(3) 0.9527(3) 0.03098(14) 0.0369(9) Uani 1 1 d . . .
H7' H 0.2123 1.0234 0.0224 0.044 Uiso 1 1 calc R . .
C2 C 0.1486(3) 0.5491(3) 0.40962(15) 0.0326(9) Uani 1 1 d . . .
H2 H 0.1763 0.5081 0.3831 0.039 Uiso 1 1 calc R . .
C4 C -0.0008(3) 0.5690(3) 0.47248(15) 0.0376(10) Uani 1 1 d . . .
H4 H -0.0706 0.5411 0.4883 0.045 Uiso 1 1 calc R . .
C12 C 0.3619(3) 0.6342(3) 0.36349(14) 0.0355(9) Uani 1 1 d . . .
H12B H 0.2961 0.6355 0.3400 0.043 Uiso 1 1 calc R . .
H12A H 0.3852 0.5529 0.3692 0.043 Uiso 1 1 calc R . .
C3 C 0.0405(3) 0.5127(3) 0.43407(16) 0.0397(10) Uani 1 1 d . . .
H3 H -0.0030 0.4475 0.4230 0.048 Uiso 1 1 calc R . .
C5' C 0.0162(3) 0.8084(3) 0.01845(14) 0.0353(9) Uani 1 1 d . . .
H5' H -0.0516 0.7813 0.0012 0.042 Uiso 1 1 calc R . .
C5 C 0.0183(3) 0.7376(3) 0.52854(14) 0.0381(10) Uani 1 1 d . . .
H5 H -0.0495 0.7104 0.5457 0.046 Uiso 1 1 calc R . .
C14' C 0.5766(3) 0.7645(3) 0.16795(14) 0.0289(8) Uani 1 1 d . . .
14A' H 0.5917 0.6822 0.1606 0.035 Uiso 1 1 calc R . .
14B' H 0.5551 0.8045 0.1387 0.035 Uiso 1 1 calc R . .
C19' C 0.9168(3) 0.8470(3) 0.18386(15) 0.0413(10) Uani 1 1 d . . .
19B' H 0.9236 0.7957 0.2107 0.062 Uiso 1 1 calc R . .
19C' H 0.9103 0.9272 0.1945 0.062 Uiso 1 1 calc R . .
19A' H 0.9890 0.8386 0.1643 0.062 Uiso 1 1 calc R . .
C18 C 0.9188(3) 0.7866(3) 0.36478(15) 0.0411(10) Uani 1 1 d . . .
H18C H 0.9111 0.8678 0.3558 0.062 Uiso 1 1 calc R . .
H18A H 0.9254 0.7386 0.3369 0.062 Uiso 1 1 calc R . .
H18B H 0.9918 0.7766 0.3839 0.062 Uiso 1 1 calc R . .
O26 O 0.2004(4) 0.9639(5) 0.2437(3) 0.149(3) Uani 0.90 1 d P . .
H26 H 0.2750 0.9728 0.2482 0.223 Uiso 0.90 1 calc PR . .
C27 C 0.1530(5) 0.8885(6) 0.2774(3) 0.090(2) Uani 0.90 1 d P . .
H27B H 0.1501 0.8100 0.2649 0.135 Uiso 0.90 1 calc PR . .
H27A H 0.0708 0.9132 0.2859 0.135 Uiso 0.90 1 calc PR . .
H27C H 0.2052 0.8898 0.3050 0.135 Uiso 0.90 1 calc PR . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O11 C1 1.381(4) . ?
O11 C12 1.422(4) . ?
O15 C13 1.412(4) . ?
O15 H15 0.8200 . ?
O11' C1' 1.365(4) . ?
O11' C12' 1.429(4) . ?
N16 C14 1.494(4) . ?
N16 C17 1.499(4) . ?
N16 H16B 0.9000 . ?
N16 H16A 0.9000 . ?
O21 C22 1.235(4) . ?
C17 C19 1.507(5) . ?
C17 C18 1.514(5) . ?
C17 H17 0.9800 . ?
O24 C23 1.263(4) . ?
O15' C13' 1.420(4) . ?
O15' H15' 0.8200 . ?
O25 C23 1.238(4) . ?
O20 C22 1.275(4) . ?
N16' C14' 1.486(4) . ?
N16' C17' 1.506(4) . ?
N16' 16A' 0.9000 . ?
N16' 16B' 0.9000 . ?
C10 C4 1.414(5) . ?
C10 C5 1.418(5) . ?
C10 C9 1.420(5) . ?
C10' C5' 1.410(5) . ?
C10' C4' 1.414(5) . ?
C10' C9' 1.419(5) . ?
C1' C2' 1.371(4) . ?
C1' C9' 1.431(5) . ?
C13' C14' 1.512(5) . ?
C13' C12' 1.519(5) . ?
C13' H13' 0.9800 . ?
C9 C1 1.412(5) . ?
C9 C8 1.429(5) . ?
C1 C2 1.360(5) . ?
C23 C22 1.551(5) . ?
C14 C13 1.510(5) . ?
C14 H14B 0.9700 . ?
C14 H14A 0.9700 . ?
C13 C12 1.520(5) . ?
C13 H13 0.9800 . ?
C8' C7' 1.366(5) . ?
C8' C9' 1.398(4) . ?
C8' H8' 0.9300 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C19 H19A 0.9600 . ?
C8 C7 1.369(5) . ?
C8 H8 0.9300 . ?
C4' C3' 1.356(5) . ?
C4' H4' 0.9300 . ?
C2' C3' 1.406(5) . ?
C2' H2' 0.9300 . ?
C6 C5 1.363(5) . ?
C6 C7 1.403(5) . ?
C6 H6 0.9300 . ?
C12' 12B' 0.9700 . ?
C12' 12A' 0.9700 . ?
C17' C18' 1.513(5) . ?
C17' C19' 1.516(5) . ?
C17' H17' 0.9800 . ?
C7 H7 0.9300 . ?
C3' H3' 0.9300 . ?
C6' C5' 1.362(5) . ?
C6' C7' 1.399(5) . ?
C6' H6' 0.9300 . ?
C18' 18B' 0.9600 . ?
C18' 18C' 0.9600 . ?
C18' 18A' 0.9600 . ?
C7' H7' 0.9300 . ?
C2 C3 1.415(5) . ?
C2 H2 0.9300 . ?
C4 C3 1.336(5) . ?
C4 H4 0.9300 . ?
C12 H12B 0.9700 . ?
C12 H12A 0.9700 . ?
C3 H3 0.9300 . ?
C5' H5' 0.9300 . ?
C5 H5 0.9300 . ?
C14' 14A' 0.9700 . ?
C14' 14B' 0.9700 . ?
C19' 19B' 0.9600 . ?
C19' 19C' 0.9600 . ?
C19' 19A' 0.9600 . ?
C18 H18C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
O26 C27 1.379(7) . ?
O26 H26 0.8200 . ?
C27 H27B 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27C 0.9600 . ?

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
_geom_angle_publ_flag
C1 O11 C12 117.3(3) . . ?
C13 O15 H15 109.5 . . ?
C1' O11' C12' 116.8(3) . . ?
C14 N16 C17 114.8(3) . . ?
C14 N16 H16B 108.6 . . ?
C17 N16 H16B 108.6 . . ?
C14 N16 H16A 108.6 . . ?
C17 N16 H16A 108.6 . . ?
H16B N16 H16A 107.5 . . ?
N16 C17 C19 109.9(3) . . ?
N16 C17 C18 108.4(3) . . ?
C19 C17 C18 112.4(3) . . ?
N16 C17 H17 108.7 . . ?
C19 C17 H17 108.7 . . ?
C18 C17 H17 108.7 . . ?
C13' O15' H15' 109.5 . . ?
C14' N16' C17' 114.8(3) . . ?
C14' N16' 16A' 108.6 . . ?
C17' N16' 16A' 108.6 . . ?
C14' N16' 16B' 108.6 . . ?
C17' N16' 16B' 108.6 . . ?
16A' N16' 16B' 107.5 . . ?
C4 C10 C5 123.4(3) . . ?
C4 C10 C9 118.4(3) . . ?
C5 C10 C9 118.2(3) . . ?
C5' C10' C4' 122.8(3) . . ?
C5' C10' C9' 118.5(3) . . ?
C4' C10' C9' 118.7(3) . . ?
O11' C1' C2' 125.0(3) . . ?
O11' C1' C9' 114.5(3) . . ?
C2' C1' C9' 120.5(3) . . ?
O15' C13' C14' 110.6(3) . . ?
O15' C13' C12' 108.7(3) . . ?
C14' C13' C12' 111.6(3) . . ?
O15' C13' H13' 108.6 . . ?
C14' C13' H13' 108.6 . . ?
C12' C13' H13' 108.6 . . ?
C1 C9 C10 119.0(3) . . ?
C1 C9 C8 122.4(3) . . ?
C10 C9 C8 118.5(3) . . ?
C2 C1 O11 124.6(3) . . ?
C2 C1 C9 121.1(3) . . ?
O11 C1 C9 114.3(3) . . ?
O25 C23 O24 125.2(3) . . ?
O25 C23 C22 118.5(3) . . ?
O24 C23 C22 116.3(3) . . ?
N16 C14 C13 112.3(3) . . ?
N16 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
N16 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
H14B C14 H14A 107.9 . . ?
O15 C13 C14 111.0(3) . . ?
O15 C13 C12 107.7(3) . . ?
C14 C13 C12 111.6(3) . . ?
O15 C13 H13 108.8 . . ?
C14 C13 H13 108.8 . . ?
C12 C13 H13 108.8 . . ?
C7' C8' C9' 121.1(3) . . ?
C7' C8' H8' 119.4 . . ?
C9' C8' H8' 119.4 . . ?
O21 C22 O20 125.2(3) . . ?
O21 C22 C23 119.6(3) . . ?
O20 C22 C23 115.2(3) . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
H19B C19 H19A 109.5 . . ?
H19C C19 H19A 109.5 . . ?
C7 C8 C9 120.8(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C3' C4' C10' 120.7(3) . . ?
C3' C4' H4' 119.7 . . ?
C10' C4' H4' 119.7 . . ?
C1' C2' C3' 119.4(4) . . ?
C1' C2' H2' 120.3 . . ?
C3' C2' H2' 120.3 . . ?
C5 C6 C7 119.4(4) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
O11' C12' C13' 107.9(3) . . ?
O11' C12' 12B' 110.1 . . ?
C13' C12' 12B' 110.1 . . ?
O11' C12' 12A' 110.1 . . ?
C13' C12' 12A' 110.1 . . ?
12B' C12' 12A' 108.4 . . ?
N16' C17' C18' 110.8(3) . . ?
N16' C17' C19' 108.7(3) . . ?
C18' C17' C19' 111.7(3) . . ?
N16' C17' H17' 108.5 . . ?
C18' C17' H17' 108.5 . . ?
C19' C17' H17' 108.5 . . ?
C8 C7 C6 120.7(3) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C8' C9' C10' 119.0(3) . . ?
C8' C9' C1' 122.0(3) . . ?
C10' C9' C1' 118.9(3) . . ?
C4' C3' C2' 121.6(3) . . ?
C4' C3' H3' 119.2 . . ?
C2' C3' H3' 119.2 . . ?
C5' C6' C7' 120.3(4) . . ?
C5' C6' H6' 119.8 . . ?
C7' C6' H6' 119.8 . . ?
C17' C18' 18B' 109.5 . . ?
C17' C18' 18C' 109.5 . . ?
18B' C18' 18C' 109.5 . . ?
C17' C18' 18A' 109.5 . . ?
18B' C18' 18A' 109.5 . . ?
18C' C18' 18A' 109.5 . . ?
C8' C7' C6' 120.0(3) . . ?
C8' C7' H7' 120.0 . . ?
C6' C7' H7' 120.0 . . ?
C1 C2 C3 118.7(4) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C3 C4 C10 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C10 C4 H4 119.7 . . ?
O11 C12 C13 108.0(3) . . ?
O11 C12 H12B 110.1 . . ?
C13 C12 H12B 110.1 . . ?
O11 C12 H12A 110.1 . . ?
C13 C12 H12A 110.1 . . ?
H12B C12 H12A 108.4 . . ?
C4 C3 C2 122.1(4) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C6' C5' C10' 120.9(3) . . ?
C6' C5' H5' 119.6 . . ?
C10' C5' H5' 119.6 . . ?
C6 C5 C10 122.3(4) . . ?
C6 C5 H5 118.8 . . ?
C10 C5 H5 118.8 . . ?
N16' C14' C13' 111.1(3) . . ?
N16' C14' 14A' 109.4 . . ?
C13' C14' 14A' 109.4 . . ?
N16' C14' 14B' 109.4 . . ?
C13' C14' 14B' 109.4 . . ?
14A' C14' 14B' 108.0 . . ?
C17' C19' 19B' 109.5 . . ?
C17' C19' 19C' 109.5 . . ?
19B' C19' 19C' 109.5 . . ?
C17' C19' 19A' 109.5 . . ?
19B' C19' 19A' 109.5 . . ?
19C' C19' 19A' 109.5 . . ?
C17 C18 H18C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
H18C C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18C C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C27 O26 H26 109.5 . . ?
O26 C27 H27B 109.5 . . ?
O26 C27 H27A 109.5 . . ?
H27B C27 H27A 109.5 . . ?
O26 C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 N16 C17 C19 -70.3(3) . . . . ?
C14 N16 C17 C18 166.5(3) . . . . ?
C12' O11' C1' C2' -7.5(5) . . . . ?
C12' O11' C1' C9' 172.9(3) . . . . ?
C4 C10 C9 C1 -3.5(5) . . . . ?
C5 C10 C9 C1 179.5(3) . . . . ?
C4 C10 C9 C8 174.5(3) . . . . ?
C5 C10 C9 C8 -2.5(5) . . . . ?
C12 O11 C1 C2 7.7(5) . . . . ?
C12 O11 C1 C9 -172.3(3) . . . . ?
C10 C9 C1 C2 4.9(5) . . . . ?
C8 C9 C1 C2 -173.0(3) . . . . ?
C10 C9 C1 O11 -175.1(3) . . . . ?
C8 C9 C1 O11 6.9(5) . . . . ?
C17 N16 C14 C13 -179.5(3) . . . . ?
N16 C14 C13 O15 -64.5(4) . . . . ?
N16 C14 C13 C12 175.3(3) . . . . ?
O25 C23 C22 O21 154.1(3) . . . . ?
O24 C23 C22 O21 -24.9(4) . . . . ?
O25 C23 C22 O20 -25.7(4) . . . . ?
O24 C23 C22 O20 155.3(3) . . . . ?
C1 C9 C8 C7 179.1(3) . . . . ?
C10 C9 C8 C7 1.1(5) . . . . ?
C5' C10' C4' C3' -176.9(3) . . . . ?
C9' C10' C4' C3' 1.9(5) . . . . ?
O11' C1' C2' C3' -177.9(3) . . . . ?
C9' C1' C2' C3' 1.7(5) . . . . ?
C1' O11' C12' C13' -175.3(3) . . . . ?
O15' C13' C12' O11' 59.1(4) . . . . ?
C14' C13' C12' O11' -63.1(4) . . . . ?
C14' N16' C17' C18' 68.9(3) . . . . ?
C14' N16' C17' C19' -167.9(3) . . . . ?
C9 C8 C7 C6 0.7(5) . . . . ?
C5 C6 C7 C8 -1.2(5) . . . . ?
C7' C8' C9' C10' -2.5(5) . . . . ?
C7' C8' C9' C1' -178.6(3) . . . . ?
C5' C10' C9' C8' 3.8(5) . . . . ?
C4' C10' C9' C8' -175.0(3) . . . . ?
C5' C10' C9' C1' -180.0(3) . . . . ?
C4' C10' C9' C1' 1.2(5) . . . . ?
O11' C1' C9' C8' -7.3(5) . . . . ?
C2' C1' C9' C8' 173.1(3) . . . . ?
O11' C1' C9' C10' 176.6(3) . . . . ?
C2' C1' C9' C10' -3.0(5) . . . . ?
C10' C4' C3' C2' -3.3(6) . . . . ?
C1' C2' C3' C4' 1.5(6) . . . . ?
C9' C8' C7' C6' -0.2(5) . . . . ?
C5' C6' C7' C8' 1.6(5) . . . . ?
O11 C1 C2 C3 177.2(3) . . . . ?
C9 C1 C2 C3 -2.9(5) . . . . ?
C5 C10 C4 C3 176.9(4) . . . . ?
C9 C10 C4 C3 0.1(5) . . . . ?
C1 O11 C12 C13 173.0(3) . . . . ?
O15 C13 C12 O11 -58.0(4) . . . . ?
C14 C13 C12 O11 64.1(4) . . . . ?
C10 C4 C3 C2 2.1(6) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
C7' C6' C5' C10' -0.2(5) . . . . ?
C4' C10' C5' C6' 176.2(3) . . . . ?
C9' C10' C5' C6' -2.5(5) . . . . ?
C7 C6 C5 C10 -0.3(5) . . . . ?
C4 C10 C5 C6 -174.7(3) . . . . ?
C9 C10 C5 C6 2.2(5) . . . . ?
C17' N16' C14' C13' -178.6(3) . . . . ?
O15' C13' C14' N16' 65.9(4) . . . . ?
C12' C13' C14' N16' -173.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        32.04
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.053
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_pro-oxa-2-1
_database_code_depnum_ccdc_archive 'CCDC 1407382'
_audit_update_record             
;
2015-06-17 deposited with the CCDC.
2015-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'Propranolol oxalate (2:1)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H22 N O2, 0.5(C2 O4)'
_chemical_formula_sum            'C17 H22 N O4'
_chemical_formula_weight         304.36

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.9928(6)
_cell_length_b                   6.4517(3)
_cell_length_c                   19.8420(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.600(2)
_cell_angle_gamma                90.00
_cell_volume                     1593.95(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    14795
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.878

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             652.0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'φ and ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6582
_diffrn_reflns_av_R_equivalents  0.1336
_diffrn_reflns_av_sigmaI/netI    0.1934
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.33
_diffrn_reflns_theta_max         27.83
_reflns_number_total             3782
_reflns_number_gt                1647
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'KappaCCD Server Software (Nonius, 1997)'
_computing_cell_refinement       'HKL Scalepack (Otwinovski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinovski & Minor, 1997)'
_computing_structure_solution    'SIR2011 (Burla, 2012)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2012)'
_computing_publication_material  
;
SHELXL-97 (Sheldrick, 2008), 
PLATON (Spek, 2009) and publCIF (Westrip, 2010)
;

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1592P)²+12.9398P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3782
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2767
_refine_ls_R_factor_gt           0.1619
_refine_ls_wR_factor_ref         0.4529
_refine_ls_wR_factor_gt          0.3990
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.7037(6) 0.2173(12) 0.6423(4) 0.0328(19) Uani 1 1 d . . .
C2 C 0.6447(7) 0.1503(13) 0.6866(5) 0.042(2) Uani 1 1 d . . .
H2 H 0.6652 0.0305 0.7132 0.050 Uiso 1 1 calc R . .
C3 C 0.5551(7) 0.2610(15) 0.6916(5) 0.044(2) Uani 1 1 d . . .
H3 H 0.5170 0.2135 0.7217 0.052 Uiso 1 1 calc R . .
C4 C 0.5218(7) 0.4351(15) 0.6540(5) 0.045(2) Uani 1 1 d . . .
H4 H 0.4616 0.5060 0.6582 0.054 Uiso 1 1 calc R . .
C5 C 0.5498(8) 0.6914(14) 0.5667(5) 0.047(2) Uani 1 1 d . . .
H5 H 0.4910 0.7670 0.5710 0.057 Uiso 1 1 calc R . .
C6 C 0.6025(8) 0.7592(14) 0.5218(5) 0.047(2) Uani 1 1 d . . .
H6 H 0.5799 0.8781 0.4952 0.056 Uiso 1 1 calc R . .
C7 C 0.6918(7) 0.6483(14) 0.5156(5) 0.043(2) Uani 1 1 d . . .
H7 H 0.7287 0.6960 0.4848 0.051 Uiso 1 1 calc R . .
C8 C 0.7264(7) 0.4734(13) 0.5531(4) 0.038(2) Uani 1 1 d . . .
H8 H 0.7858 0.4016 0.5479 0.045 Uiso 1 1 calc R . .
C9 C 0.6697(6) 0.4006(11) 0.6011(4) 0.0277(17) Uani 1 1 d . . .
C10 C 0.5796(7) 0.5093(13) 0.6079(5) 0.041(2) Uani 1 1 d . . .
O11 O 0.7905(5) 0.1223(8) 0.6318(3) 0.0405(15) Uani 1 1 d . . .
C12 C 0.8290(7) -0.0599(13) 0.6713(4) 0.037(2) Uani 1 1 d . . .
H12B H 0.7720 -0.1616 0.6647 0.044 Uiso 1 1 calc R . .
H12A H 0.8556 -0.0275 0.7210 0.044 Uiso 1 1 calc R . .
C13 C 0.9181(7) -0.1418(11) 0.6444(5) 0.035(2) Uani 1 1 d . . .
H13 H 0.8905 -0.1633 0.5935 0.042 Uiso 1 1 calc R . .
C14 C 1.0142(6) 0.0059(12) 0.6593(4) 0.0290(17) Uani 1 1 d . . .
H14B H 0.9890 0.1465 0.6476 0.035 Uiso 1 1 calc R . .
H14A H 1.0528 0.0017 0.7090 0.035 Uiso 1 1 calc R . .
O15 O 0.9472(5) -0.3369(8) 0.6778(3) 0.0421(16) Uani 1 1 d . . .
H15 H 0.9600 -0.4189 0.6496 0.063 Uiso 1 1 calc R . .
N16 N 1.0878(5) -0.0543(9) 0.6170(3) 0.0254(14) Uani 1 1 d . . .
H16B H 1.0794 0.0376 0.5817 0.030 Uiso 1 1 calc R . .
H16A H 1.0669 -0.1788 0.5975 0.030 Uiso 1 1 calc R . .
C17 C 1.2055(7) -0.0663(13) 0.6558(5) 0.039(2) Uani 1 1 d . . .
H17 H 1.2154 -0.1629 0.6953 0.047 Uiso 1 1 calc R . .
C18 C 1.2651(9) -0.1475(17) 0.6066(6) 0.062(3) Uani 1 1 d . . .
H18C H 1.2386 -0.2829 0.5904 0.093 Uiso 1 1 calc R . .
H18B H 1.3404 -0.1558 0.6309 0.093 Uiso 1 1 calc R . .
H18A H 1.2544 -0.0556 0.5671 0.093 Uiso 1 1 calc R . .
C19 C 1.2427(8) 0.1479(16) 0.6846(6) 0.059(3) Uani 1 1 d . . .
H19A H 1.2023 0.1913 0.7157 0.088 Uiso 1 1 calc R . .
H19C H 1.2316 0.2444 0.6464 0.088 Uiso 1 1 calc R . .
H19B H 1.3176 0.1432 0.7098 0.088 Uiso 1 1 calc R . .
O20 O 1.0359(5) 0.2393(8) 0.5137(3) 0.0393(15) Uani 1 1 d . . .
O21 O 1.0584(5) 0.5003(8) 0.5920(3) 0.0418(16) Uani 1 1 d . . .
C22 C 1.0265(6) 0.4286(11) 0.5311(4) 0.0251(16) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O11 1.351(10) . ?
C1 C2 1.390(12) . ?
C1 C9 1.434(11) . ?
C2 C3 1.394(13) . ?
C2 H2 0.9300 . ?
C3 C4 1.349(13) . ?
C3 H3 0.9300 . ?
C4 C10 1.422(13) . ?
C4 H4 0.9300 . ?
C5 C6 1.342(13) . ?
C5 C10 1.421(13) . ?
C5 H5 0.9300 . ?
C6 C7 1.399(13) . ?
C6 H6 0.9300 . ?
C7 C8 1.356(12) . ?
C7 H7 0.9300 . ?
C8 C9 1.440(11) . ?
C8 H8 0.9300 . ?
C9 C10 1.403(12) . ?
O11 C12 1.422(9) . ?
C12 C13 1.502(12) . ?
C12 H12B 0.9700 . ?
C12 H12A 0.9700 . ?
C13 O15 1.422(9) . ?
C13 C14 1.531(11) . ?
C13 H13 0.9800 . ?
C14 N16 1.492(9) . ?
C14 H14B 0.9700 . ?
C14 H14A 0.9700 . ?
O15 H15 0.8200 . ?
N16 C17 1.505(10) . ?
N16 H16B 0.9000 . ?
N16 H16A 0.9000 . ?
C17 C18 1.504(12) . ?
C17 C19 1.520(13) . ?
C17 H17 0.9800 . ?
C18 H18C 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18A 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19C 0.9600 . ?
C19 H19B 0.9600 . ?
O20 C22 1.285(9) . ?
O21 C22 1.250(9) . ?
C22 C22 1.536(15) 3_766 ?

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
_geom_angle_publ_flag
O11 C1 C2 126.3(8) . . ?
O11 C1 C9 114.9(7) . . ?
C2 C1 C9 118.8(7) . . ?
C1 C2 C3 120.5(8) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 122.0(9) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C3 C4 C10 119.4(9) . . ?
C3 C4 H4 120.3 . . ?
C10 C4 H4 120.3 . . ?
C6 C5 C10 123.0(9) . . ?
C6 C5 H5 118.5 . . ?
C10 C5 H5 118.5 . . ?
C5 C6 C7 119.0(9) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C8 C7 C6 122.1(9) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C7 C8 C9 118.9(8) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C10 C9 C1 119.1(7) . . ?
C10 C9 C8 120.0(7) . . ?
C1 C9 C8 120.9(7) . . ?
C9 C10 C5 117.1(8) . . ?
C9 C10 C4 120.1(8) . . ?
C5 C10 C4 122.8(9) . . ?
C1 O11 C12 117.9(6) . . ?
O11 C12 C13 106.3(6) . . ?
O11 C12 H12B 110.5 . . ?
C13 C12 H12B 110.5 . . ?
O11 C12 H12A 110.5 . . ?
C13 C12 H12A 110.5 . . ?
H12B C12 H12A 108.7 . . ?
O15 C13 C12 106.0(6) . . ?
O15 C13 C14 111.5(7) . . ?
C12 C13 C14 112.4(7) . . ?
O15 C13 H13 108.9 . . ?
C12 C13 H13 108.9 . . ?
C14 C13 H13 108.9 . . ?
N16 C14 C13 110.4(6) . . ?
N16 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
N16 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
H14B C14 H14A 108.1 . . ?
C13 O15 H15 109.5 . . ?
C14 N16 C17 116.5(6) . . ?
C14 N16 H16B 108.2 . . ?
C17 N16 H16B 108.2 . . ?
C14 N16 H16A 108.2 . . ?
C17 N16 H16A 108.2 . . ?
H16B N16 H16A 107.3 . . ?
C18 C17 N16 108.8(7) . . ?
C18 C17 C19 113.2(9) . . ?
N16 C17 C19 108.2(7) . . ?
C18 C17 H17 108.9 . . ?
N16 C17 H17 108.9 . . ?
C19 C17 H17 108.9 . . ?
C17 C18 H18C 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18C C18 H18B 109.5 . . ?
C17 C18 H18A 109.5 . . ?
H18C C18 H18A 109.5 . . ?
H18B C18 H18A 109.5 . . ?
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 . . ?
O21 C22 O20 125.5(7) . . ?
O21 C22 C22 120.2(8) . 3_766 ?
O20 C22 C22 114.2(8) . 3_766 ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 C1 C2 C3 -178.6(8) . . . . ?
C9 C1 C2 C3 -0.9(12) . . . . ?
C1 C2 C3 C4 0.3(14) . . . . ?
C2 C3 C4 C10 -0.2(14) . . . . ?
C10 C5 C6 C7 -0.9(15) . . . . ?
C5 C6 C7 C8 0.6(15) . . . . ?
C6 C7 C8 C9 -0.4(13) . . . . ?
O11 C1 C9 C10 179.5(7) . . . . ?
C2 C1 C9 C10 1.5(11) . . . . ?
O11 C1 C9 C8 -0.4(11) . . . . ?
C2 C1 C9 C8 -178.4(8) . . . . ?
C7 C8 C9 C10 0.6(12) . . . . ?
C7 C8 C9 C1 -179.5(8) . . . . ?
C1 C9 C10 C5 179.2(7) . . . . ?
C8 C9 C10 C5 -0.9(12) . . . . ?
C1 C9 C10 C4 -1.4(12) . . . . ?
C8 C9 C10 C4 178.4(8) . . . . ?
C6 C5 C10 C9 1.1(13) . . . . ?
C6 C5 C10 C4 -178.2(10) . . . . ?
C3 C4 C10 C9 0.8(13) . . . . ?
C3 C4 C10 C5 -179.9(9) . . . . ?
C2 C1 O11 C12 -2.6(12) . . . . ?
C9 C1 O11 C12 179.6(7) . . . . ?
C1 O11 C12 C13 174.9(7) . . . . ?
O11 C12 C13 O15 -173.0(6) . . . . ?
O11 C12 C13 C14 64.9(9) . . . . ?
O15 C13 C14 N16 75.1(8) . . . . ?
C12 C13 C14 N16 -166.0(6) . . . . ?
C13 C14 N16 C17 -132.3(7) . . . . ?
C14 N16 C17 C18 174.8(7) . . . . ?
C14 N16 C17 C19 -61.8(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        27.83
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.572
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.110
