# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_p21n
_database_code_depnum_ccdc_archive 'CCDC 1883843'
loop_
_audit_author_name
_audit_author_address
'Manuela Silva'
;University of Coimbra
Portugal
;
_audit_update_record             
;
2019-04-17 deposited with the CCDC.	2019-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 1-[4-(2-methoxyethyl)phenoxy]-3-(propan-2-ylamino)propan-2-ol]  
;
_chemical_name_common            metropolol
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H25 N O3'
_chemical_formula_sum            'C15 H25 N O3'
_chemical_formula_weight         267.36

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   P21/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                   16.54(2)
_cell_length_b                   5.411(7)
_cell_length_c                   17.90(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.47(2)
_cell_angle_gamma                90.00
_cell_volume                     1575(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    378
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      25.27

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8886
_exptl_absorpt_correction_T_max  0.9999
_exptl_absorpt_process_details   '(SADABS;  Sheldrick, 2000)'

_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  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_reflns_number            12766
_diffrn_reflns_av_R_equivalents  0.5624
_diffrn_reflns_av_sigmaI/netI    0.5966
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         25.30
_reflns_number_total             2843
_reflns_number_gt                584
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'APEX2 (Bruker, 2003)'
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL97

_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)+(0.0282P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2843
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.4226
_refine_ls_R_factor_gt           0.0790
_refine_ls_wR_factor_ref         0.1541
_refine_ls_wR_factor_gt          0.0901
_refine_ls_goodness_of_fit_ref   0.857
_refine_ls_restrained_S_all      0.857
_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
O1 O 0.5886(2) 0.9029(8) 0.3112(3) 0.0515(15) Uani 1 1 d . . .
O2 O 0.4943(2) 0.7606(7) 0.4292(3) 0.0454(14) Uani 1 1 d . . .
H2O H 0.468(3) 0.878(10) 0.430(4) 0.068 Uiso 1 1 d . . .
O3 O 0.6229(3) 0.4780(10) -0.0274(3) 0.090(2) Uani 1 1 d . . .
N1 N 0.5872(3) 0.7786(10) 0.5777(3) 0.0474(19) Uani 1 1 d . . .
H1N H 0.545(3) 0.690(10) 0.577(3) 0.057 Uiso 1 1 d . . .
C1 C 0.6162(4) 0.8638(13) 0.2448(4) 0.042(2) Uani 1 1 d . . .
C2 C 0.6653(4) 0.6764(12) 0.2305(3) 0.047(2) Uani 1 1 d . . .
H2 H 0.6824 0.5582 0.2678 0.056 Uiso 1 1 calc R . .
C3 C 0.6906(3) 0.6586(13) 0.1605(4) 0.049(2) Uani 1 1 d . . .
H3 H 0.7227 0.5255 0.1508 0.058 Uiso 1 1 calc R . .
C4 C 0.6684(4) 0.8363(13) 0.1054(4) 0.040(2) Uani 1 1 d . . .
C5 C 0.6188(4) 1.0272(13) 0.1203(4) 0.055(2) Uani 1 1 d . . .
H5 H 0.6023 1.1475 0.0836 0.065 Uiso 1 1 calc R . .
C6 C 0.5932(4) 1.0414(12) 0.1898(4) 0.052(2) Uani 1 1 d . . .
H6 H 0.5601 1.1723 0.1995 0.062 Uiso 1 1 calc R . .
C7 C 0.6159(3) 0.7384(11) 0.3731(3) 0.043(2) Uani 1 1 d . . .
H7A H 0.6755 0.7398 0.3863 0.052 Uiso 1 1 calc R . .
H7B H 0.5980 0.5710 0.3595 0.052 Uiso 1 1 calc R . .
C8 C 0.5784(4) 0.8286(11) 0.4400(4) 0.040(2) Uani 1 1 d . . .
H8 H 0.5832 1.0088 0.4438 0.048 Uiso 1 1 calc R . .
C9 C 0.6247(3) 0.7114(11) 0.5125(3) 0.049(2) Uani 1 1 d . . .
H9A H 0.6242 0.5330 0.5069 0.059 Uiso 1 1 calc R . .
H9B H 0.6815 0.7661 0.5213 0.059 Uiso 1 1 calc R . .
C10 C 0.6412(4) 0.7333(13) 0.6515(3) 0.051(2) Uani 1 1 d . . .
H10 H 0.6691 0.5745 0.6488 0.061 Uiso 1 1 calc R . .
C11 C 0.7050(4) 0.9313(13) 0.6671(4) 0.101(3) Uani 1 1 d . . .
H11A H 0.7376 0.9310 0.6279 0.152 Uiso 1 1 calc R . .
H11B H 0.7397 0.9011 0.7154 0.152 Uiso 1 1 calc R . .
H11C H 0.6786 1.0890 0.6682 0.152 Uiso 1 1 calc R . .
C12 C 0.5900(4) 0.7173(14) 0.7135(3) 0.091(3) Uani 1 1 d . . .
H12A H 0.5504 0.5868 0.7019 0.136 Uiso 1 1 calc R . .
H12B H 0.5620 0.8712 0.7167 0.136 Uiso 1 1 calc R . .
H12C H 0.6253 0.6836 0.7613 0.136 Uiso 1 1 calc R . .
C13 C 0.6950(4) 0.8188(13) 0.0285(4) 0.062(2) Uani 1 1 d . . .
H13A H 0.7111 0.9824 0.0144 0.075 Uiso 1 1 calc R . .
H13B H 0.7433 0.7139 0.0338 0.075 Uiso 1 1 calc R . .
C14 C 0.6314(5) 0.7197(14) -0.0353(4) 0.080(3) Uani 1 1 d . . .
H14A H 0.5792 0.8011 -0.0351 0.096 Uiso 1 1 calc R . .
H14B H 0.6479 0.7539 -0.0836 0.096 Uiso 1 1 calc R . .
C15 C 0.5611(4) 0.3763(13) -0.0879(4) 0.109(3) Uani 1 1 d . . .
H15A H 0.5086 0.4490 -0.0858 0.163 Uiso 1 1 calc R . .
H15B H 0.5580 0.2005 -0.0817 0.163 Uiso 1 1 calc R . .
H15C H 0.5759 0.4124 -0.1362 0.163 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
O1 C1 1.364(7) . ?
O1 C7 1.430(6) . ?
O2 C8 1.417(7) . ?
O2 H2O 0.77(5) . ?
O3 C14 1.325(7) . ?
O3 C15 1.456(7) . ?
N1 C9 1.464(7) . ?
N1 C10 1.474(7) . ?
N1 H1N 0.84(5) . ?
C1 C2 1.353(7) . ?
C1 C6 1.378(8) . ?
C2 C3 1.396(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(8) . ?
C4 C13 1.522(7) . ?
C5 C6 1.388(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.524(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.521(7) . ?
C8 H8 0.9800 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.494(7) . ?
C10 C12 1.516(7) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.504(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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 O1 C7 118.1(5) . . ?
C8 O2 H2O 109(4) . . ?
C14 O3 C15 111.5(6) . . ?
C9 N1 C10 113.4(5) . . ?
C9 N1 H1N 108(4) . . ?
C10 N1 H1N 107(4) . . ?
C2 C1 O1 126.0(7) . . ?
C2 C1 C6 119.1(6) . . ?
O1 C1 C6 114.9(7) . . ?
C1 C2 C3 120.6(7) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 120.7(6) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 118.4(7) . . ?
C5 C4 C13 120.2(7) . . ?
C3 C4 C13 121.4(7) . . ?
C4 C5 C6 120.4(7) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 120.8(7) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
O1 C7 C8 107.0(5) . . ?
O1 C7 H7A 110.3 . . ?
C8 C7 H7A 110.3 . . ?
O1 C7 H7B 110.3 . . ?
C8 C7 H7B 110.3 . . ?
H7A C7 H7B 108.6 . . ?
O2 C8 C9 109.7(5) . . ?
O2 C8 C7 109.9(5) . . ?
C9 C8 C7 108.8(5) . . ?
O2 C8 H8 109.5 . . ?
C9 C8 H8 109.5 . . ?
C7 C8 H8 109.5 . . ?
N1 C9 C8 110.9(5) . . ?
N1 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.0 . . ?
N1 C10 C11 109.9(6) . . ?
N1 C10 C12 109.7(5) . . ?
C11 C10 C12 111.9(6) . . ?
N1 C10 H10 108.4 . . ?
C11 C10 H10 108.4 . . ?
C12 C10 H10 108.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C4 115.5(5) . . ?
C14 C13 H13A 108.4 . . ?
C4 C13 H13A 108.4 . . ?
C14 C13 H13B 108.4 . . ?
C4 C13 H13B 108.4 . . ?
H13A C13 H13B 107.5 . . ?
O3 C14 C13 110.1(7) . . ?
O3 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
O3 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C7 O1 C1 C2 2.5(9) . . . . ?
C7 O1 C1 C6 -174.6(5) . . . . ?
O1 C1 C2 C3 -178.9(6) . . . . ?
C6 C1 C2 C3 -1.8(10) . . . . ?
C1 C2 C3 C4 2.3(10) . . . . ?
C2 C3 C4 C5 -1.9(10) . . . . ?
C2 C3 C4 C13 -179.6(6) . . . . ?
C3 C4 C5 C6 1.1(10) . . . . ?
C13 C4 C5 C6 178.8(6) . . . . ?
C2 C1 C6 C5 1.0(10) . . . . ?
O1 C1 C6 C5 178.4(6) . . . . ?
C4 C5 C6 C1 -0.7(10) . . . . ?
C1 O1 C7 C8 178.3(5) . . . . ?
O1 C7 C8 O2 76.7(6) . . . . ?
O1 C7 C8 C9 -163.2(5) . . . . ?
C10 N1 C9 C8 -163.4(6) . . . . ?
O2 C8 C9 N1 -55.8(7) . . . . ?
C7 C8 C9 N1 -176.0(5) . . . . ?
C9 N1 C10 C11 77.0(7) . . . . ?
C9 N1 C10 C12 -159.6(5) . . . . ?
C5 C4 C13 C14 -78.1(8) . . . . ?
C3 C4 C13 C14 99.6(8) . . . . ?
C15 O3 C14 C13 179.5(6) . . . . ?
C4 C13 C14 O3 -73.7(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_metnic
_database_code_depnum_ccdc_archive 'CCDC 1900590'
loop_
_audit_author_name
_audit_author_address
'Manuela Ramos Silva'
;CFisUC
Portugal
;
_audit_update_record             
;
2019-03-01 deposited with the CCDC.	2019-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-hydroxy-N-isopropyl-3-(4-(2-methoxyethyl)phenoxy)propan-1-aminium nicotinate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H30 N2 O5'
_chemical_formula_weight         390.47

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

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

_cell_length_a                   8.1740(17)
_cell_length_b                   9.264(2)
_cell_length_c                   14.884(3)
_cell_angle_alpha                98.244(5)
_cell_angle_beta                 96.622(4)
_cell_angle_gamma                99.623(5)
_cell_volume                     1088.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3238
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      25.92

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             420
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_min  0.648
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS;  Sheldrick, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20284
_diffrn_reflns_av_R_equivalents  0.1117
_diffrn_reflns_av_sigmaI/netI    0.1244
_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       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         26.06
_reflns_number_total             4231
_reflns_number_gt                1811
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2003)'
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  SHELXL-97
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL-97

_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)+(0.1507P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4231
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2085
_refine_ls_R_factor_gt           0.0779
_refine_ls_wR_factor_ref         0.2763
_refine_ls_wR_factor_gt          0.2109
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_restrained_S_all      0.975
_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
O1 O 0.0834(3) 0.1181(3) 0.31265(17) 0.0666(7) Uani 1 1 d . . .
O2 O 0.1621(3) 0.3429(3) 0.53586(17) 0.0718(8) Uani 1 1 d . . .
H2A H 0.248(5) 0.399(4) 0.571(3) 0.086 Uiso 1 1 d . . .
O3 O -0.1814(5) -0.5736(4) 0.1439(3) 0.1285(13) Uani 1 1 d . . .
O4 O 0.4432(3) 0.5225(3) 0.63703(16) 0.0646(7) Uani 1 1 d . . .
O5 O 0.3081(3) 0.6981(3) 0.59573(17) 0.0813(8) Uani 1 1 d . . .
N1 N 0.2632(4) 0.5681(3) 0.4135(2) 0.0527(7) Uani 1 1 d . . .
H1A H 0.278(4) 0.601(4) 0.485(3) 0.076(11) Uiso 1 1 d . . .
H1B H 0.371(5) 0.542(4) 0.406(3) 0.091 Uiso 1 1 d . . .
N2 N 0.6489(4) 0.7894(4) 0.8871(2) 0.0822(10) Uani 1 1 d . . .
C1 C -0.0191(4) -0.0103(4) 0.2647(2) 0.0536(9) Uani 1 1 d . . .
C2 C -0.1215(4) -0.1131(4) 0.3023(3) 0.0606(10) Uani 1 1 d . . .
H2 H -0.1259 -0.0988 0.3650 0.073 Uiso 1 1 calc R . .
C3 C -0.2177(5) -0.2382(4) 0.2455(3) 0.0636(10) Uani 1 1 d . . .
H3 H -0.2847 -0.3074 0.2716 0.076 Uiso 1 1 calc R . .
C4 C -0.2174(5) -0.2634(4) 0.1513(3) 0.0618(10) Uani 1 1 d . . .
C5 C -0.1125(5) -0.1583(4) 0.1156(3) 0.0645(10) Uani 1 1 d . . .
H5 H -0.1076 -0.1724 0.0529 0.077 Uiso 1 1 calc R . .
C6 C -0.0155(5) -0.0336(4) 0.1707(3) 0.0633(10) Uani 1 1 d . . .
H6 H 0.0525 0.0350 0.1447 0.076 Uiso 1 1 calc R . .
C7 C 0.0644(5) 0.1617(4) 0.4063(2) 0.0602(10) Uani 1 1 d . . .
H7A H 0.0933 0.0878 0.4422 0.072 Uiso 1 1 calc R . .
H7B H -0.0509 0.1708 0.4110 0.072 Uiso 1 1 calc R . .
C8 C 0.1795(4) 0.3092(4) 0.4418(2) 0.0542(9) Uani 1 1 d . . .
H8 H 0.2954 0.2984 0.4365 0.065 Uiso 1 1 calc R . .
C9 C 0.1348(4) 0.4284(3) 0.3879(2) 0.0544(9) Uani 1 1 d . . .
H9A H 0.1267 0.3922 0.3228 0.065 Uiso 1 1 calc R . .
H9B H 0.0262 0.4493 0.4000 0.065 Uiso 1 1 calc R . .
C10 C 0.2258(5) 0.6967(4) 0.3659(2) 0.0598(10) Uani 1 1 d . . .
H10 H 0.1161 0.7168 0.3787 0.072 Uiso 1 1 calc R . .
C11 C 0.3566(6) 0.8326(4) 0.4069(3) 0.0937(15) Uani 1 1 d . . .
H11A H 0.4653 0.8146 0.3955 0.140 Uiso 1 1 calc R . .
H11B H 0.3551 0.8540 0.4718 0.140 Uiso 1 1 calc R . .
H11C H 0.3324 0.9156 0.3793 0.140 Uiso 1 1 calc R . .
C12 C 0.2192(5) 0.6589(4) 0.2632(2) 0.0782(12) Uani 1 1 d . . .
H12A H 0.1999 0.7431 0.2355 0.117 Uiso 1 1 calc R . .
H12B H 0.1298 0.5763 0.2394 0.117 Uiso 1 1 calc R . .
H12C H 0.3238 0.6334 0.2495 0.117 Uiso 1 1 calc R . .
C13 C -0.3216(5) -0.3975(4) 0.0902(3) 0.0779(12) Uani 1 1 d . . .
H13A H -0.3666 -0.3680 0.0339 0.093 Uiso 1 1 calc R . .
H13B H -0.4156 -0.4344 0.1201 0.093 Uiso 1 1 calc R . .
C14 C -0.2293(8) -0.5219(5) 0.0661(4) 0.1181(19) Uani 1 1 d . . .
H14A H -0.3017 -0.6010 0.0224 0.142 Uiso 1 1 calc R . .
H14B H -0.1317 -0.4862 0.0386 0.142 Uiso 1 1 calc R . .
C15 C -0.1038(8) -0.6992(5) 0.1246(4) 0.144(2) Uani 1 1 d . . .
H15A H -0.1748 -0.7712 0.0772 0.217 Uiso 1 1 calc R . .
H15B H -0.0865 -0.7423 0.1790 0.217 Uiso 1 1 calc R . .
H15C H 0.0022 -0.6685 0.1046 0.217 Uiso 1 1 calc R . .
C16 C 0.4055(4) 0.6520(4) 0.6517(2) 0.0596(10) Uani 1 1 d . . .
C17 C 0.4799(4) 0.7517(4) 0.7394(2) 0.0514(9) Uani 1 1 d . . .
C18 C 0.5822(5) 0.7086(4) 0.8068(3) 0.0667(10) Uani 1 1 d . . .
H18 H 0.6066 0.6138 0.7945 0.080 Uiso 1 1 calc R . .
C19 C 0.4462(5) 0.8939(4) 0.7589(3) 0.0756(12) Uani 1 1 d . . .
H19 H 0.3793 0.9301 0.7158 0.091 Uiso 1 1 calc R . .
C20 C 0.6102(5) 0.9245(5) 0.9042(3) 0.0835(13) Uani 1 1 d . . .
H20 H 0.6519 0.9830 0.9610 0.100 Uiso 1 1 calc R . .
C21 C 0.5117(6) 0.9809(5) 0.8419(3) 0.0899(14) Uani 1 1 d . . .
H21 H 0.4899 1.0764 0.8557 0.108 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
O1 C1 1.383(4) . ?
O1 C7 1.428(4) . ?
O2 C8 1.419(4) . ?
O2 H2A 0.87(4) . ?
O3 C14 1.356(6) . ?
O3 C15 1.425(6) . ?
O4 C16 1.283(4) . ?
O5 C16 1.254(4) . ?
N1 C9 1.495(4) . ?
N1 C10 1.525(4) . ?
N1 H1A 1.06(4) . ?
N1 H1B 0.97(4) . ?
N2 C18 1.321(5) . ?
N2 C20 1.338(5) . ?
C1 C2 1.385(5) . ?
C1 C6 1.389(5) . ?
C2 C3 1.391(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.389(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(5) . ?
C4 C13 1.497(5) . ?
C5 C6 1.381(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.510(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.522(4) . ?
C8 H8 0.9800 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.509(5) . ?
C10 C12 1.511(5) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.503(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.487(5) . ?
C17 C18 1.378(5) . ?
C17 C19 1.387(5) . ?
C18 H18 0.9300 . ?
C19 C21 1.371(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.375(6) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?

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 O1 C7 117.7(3) . . ?
C8 O2 H2A 116(3) . . ?
C14 O3 C15 111.3(5) . . ?
C9 N1 C10 115.3(2) . . ?
C9 N1 H1A 108.5(19) . . ?
C10 N1 H1A 109.5(18) . . ?
C9 N1 H1B 107(2) . . ?
C10 N1 H1B 114(2) . . ?
H1A N1 H1B 101(3) . . ?
C18 N2 C20 116.3(3) . . ?
O1 C1 C2 125.8(3) . . ?
O1 C1 C6 115.1(3) . . ?
C2 C1 C6 119.2(3) . . ?
C1 C2 C3 119.5(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 122.4(4) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C3 C4 C5 116.7(3) . . ?
C3 C4 C13 122.4(4) . . ?
C5 C4 C13 120.9(4) . . ?
C6 C5 C4 121.8(4) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 120.4(4) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O1 C7 C8 108.1(3) . . ?
O1 C7 H7A 110.1 . . ?
C8 C7 H7A 110.1 . . ?
O1 C7 H7B 110.1 . . ?
C8 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
O2 C8 C7 105.6(3) . . ?
O2 C8 C9 112.3(3) . . ?
C7 C8 C9 111.3(3) . . ?
O2 C8 H8 109.2 . . ?
C7 C8 H8 109.2 . . ?
C9 C8 H8 109.2 . . ?
N1 C9 C8 111.3(3) . . ?
N1 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
N1 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C12 112.1(3) . . ?
C11 C10 N1 108.4(3) . . ?
C12 C10 N1 111.4(3) . . ?
C11 C10 H10 108.3 . . ?
C12 C10 H10 108.3 . . ?
N1 C10 H10 108.3 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C4 C13 C14 114.6(4) . . ?
C4 C13 H13A 108.6 . . ?
C14 C13 H13A 108.6 . . ?
C4 C13 H13B 108.6 . . ?
C14 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
O3 C14 C13 108.6(5) . . ?
O3 C14 H14A 110.0 . . ?
C13 C14 H14A 110.0 . . ?
O3 C14 H14B 110.0 . . ?
C13 C14 H14B 110.0 . . ?
H14A C14 H14B 108.3 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O5 C16 O4 123.1(3) . . ?
O5 C16 C17 118.5(3) . . ?
O4 C16 C17 118.5(3) . . ?
C18 C17 C19 116.0(3) . . ?
C18 C17 C16 122.7(3) . . ?
C19 C17 C16 121.4(3) . . ?
N2 C18 C17 126.0(3) . . ?
N2 C18 H18 117.0 . . ?
C17 C18 H18 117.0 . . ?
C21 C19 C17 119.9(3) . . ?
C21 C19 H19 120.1 . . ?
C17 C19 H19 120.1 . . ?
N2 C20 C21 123.1(4) . . ?
N2 C20 H20 118.4 . . ?
C21 C20 H20 118.4 . . ?
C19 C21 C20 118.8(4) . . ?
C19 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?

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
C7 O1 C1 C2 -10.3(5) . . . . ?
C7 O1 C1 C6 169.5(3) . . . . ?
O1 C1 C2 C3 -179.7(3) . . . . ?
C6 C1 C2 C3 0.5(5) . . . . ?
C1 C2 C3 C4 -1.0(5) . . . . ?
C2 C3 C4 C5 1.3(5) . . . . ?
C2 C3 C4 C13 -179.7(3) . . . . ?
C3 C4 C5 C6 -1.1(5) . . . . ?
C13 C4 C5 C6 179.9(3) . . . . ?
C4 C5 C6 C1 0.6(5) . . . . ?
O1 C1 C6 C5 179.9(3) . . . . ?
C2 C1 C6 C5 -0.3(5) . . . . ?
C1 O1 C7 C8 -176.0(3) . . . . ?
O1 C7 C8 O2 -177.0(2) . . . . ?
O1 C7 C8 C9 60.9(4) . . . . ?
C10 N1 C9 C8 -177.6(3) . . . . ?
O2 C8 C9 N1 70.3(4) . . . . ?
C7 C8 C9 N1 -171.6(3) . . . . ?
C9 N1 C10 C11 173.8(3) . . . . ?
C9 N1 C10 C12 -62.4(4) . . . . ?
C3 C4 C13 C14 -97.7(5) . . . . ?
C5 C4 C13 C14 81.2(5) . . . . ?
C15 O3 C14 C13 175.7(4) . . . . ?
C4 C13 C14 O3 64.6(6) . . . . ?
O5 C16 C17 C18 177.1(4) . . . . ?
O4 C16 C17 C18 -2.5(5) . . . . ?
O5 C16 C17 C19 -1.4(5) . . . . ?
O4 C16 C17 C19 179.1(3) . . . . ?
C20 N2 C18 C17 1.1(6) . . . . ?
C19 C17 C18 N2 0.4(6) . . . . ?
C16 C17 C18 N2 -178.1(4) . . . . ?
C18 C17 C19 C21 -1.0(6) . . . . ?
C16 C17 C19 C21 177.5(4) . . . . ?
C18 N2 C20 C21 -2.2(7) . . . . ?
C17 C19 C21 C20 0.0(7) . . . . ?
N2 C20 C21 C19 1.7(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.834
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.054
