# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Ram Thaimattam'
_publ_contact_author_email       RAMTHAIMATTAM@DRREDDYS.COM

_publ_section_title              
;
Polytypism in desvenlafaxine succinate monohydrate
;
loop_
_publ_author_name
'Ram Thaimattam'
'Surya Devarakonda'
'Naga Kiran Duggirala'
'Sundara Lakshmi Kanniah'
'Vamsee Muppidi'

# Attachment 'K4FINAL-ram.CIF'

data_k4final
_database_code_depnum_ccdc_archive 'CCDC 698527'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H26 N O2, C4 H5 O4, H2 O '
_chemical_formula_sum            'C20 H33 N O7'
_chemical_formula_weight         399.47

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
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   6.539(6)
_cell_length_b                   9.325(9)
_cell_length_c                   17.317(17)
_cell_angle_alpha                83.307(17)
_cell_angle_beta                 88.561(19)
_cell_angle_gamma                89.15(2)
_cell_volume                     1048.3(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4147
_cell_measurement_theta_min      1.2
_cell_measurement_theta_max      25.0

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9541
_exptl_absorpt_correction_T_max  0.9813
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71070
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            9472
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_av_sigmaI/netI    0.1229
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3551
_reflns_number_gt                1382
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrystalClear'
_computing_cell_refinement       CrystalClear'
_computing_data_reduction        CrystalStructure
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;
Warren L. DeLano "The PyMOL Molecular Graphics System."
DeLano Scientific LLC, San Carlos, CA, USA. http://www.pymol.org
;
_computing_publication_material  'CrystalStructure 3.8.1'

_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)+(0.0777P)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         3551
_refine_ls_number_parameters     264
_refine_ls_number_restraints     26
_refine_ls_R_factor_all          0.1367
_refine_ls_R_factor_gt           0.0672
_refine_ls_wR_factor_ref         0.1925
_refine_ls_wR_factor_gt          0.1505
_refine_ls_goodness_of_fit_ref   0.871
_refine_ls_restrained_S_all      0.871
_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 0.5571(4) -0.4511(3) 0.68197(18) 0.0610(8) Uani 1 1 d . . .
H1 H 0.6589 -0.5024 0.6782 0.073 Uiso 1 1 calc R . .
O2 O 0.8605(3) 0.3638(2) 0.66342(16) 0.0515(7) Uani 1 1 d . . .
H21 H 0.9809 0.3697 0.6747 0.062 Uiso 1 1 calc R . .
N1 N 0.6413(6) 0.1135(4) 0.8614(2) 0.0749(12) Uani 1 1 d U . .
H11 H 0.5777 0.0286 0.8574 0.090 Uiso 1 1 calc R . .
O3 O 1.5944(4) -0.2161(3) 0.90092(17) 0.0635(8) Uani 1 1 d . . .
O4 O 1.3110(4) -0.0922(3) 0.88226(19) 0.0703(9) Uani 1 1 d . . .
O5 O 0.7427(4) -0.4616(3) 0.90218(19) 0.0716(9) Uani 1 1 d . . .
H51 H 0.690(6) -0.341(5) 0.905(2) 0.086 Uiso 1 1 d . . .
O6 O 1.0277(4) -0.5805(3) 0.87943(19) 0.0695(9) Uani 1 1 d . . .
O7 O 1.2126(5) 0.3885(4) 0.7379(2) 0.0793(10) Uani 1 1 d D . .
H71 H 1.299(5) 0.448(4) 0.722(3) 0.095 Uiso 1 1 d D . .
H72 H 1.196(8) 0.388(6) 0.7850(5) 0.095 Uiso 1 1 d D . .
C1 C 0.7209(6) -0.0315(4) 0.7149(2) 0.0444(9) Uani 1 1 d . . .
C2 C 0.8656(6) -0.1407(4) 0.7168(2) 0.0494(10) Uani 1 1 d . . .
H2 H 1.0012 -0.1198 0.7254 0.059 Uiso 1 1 calc R . .
C3 C 0.8154(5) -0.2797(4) 0.7064(2) 0.0465(9) Uani 1 1 d . . .
H3 H 0.9168 -0.3510 0.7083 0.056 Uiso 1 1 calc R . .
C4 C 0.6159(6) -0.3141(4) 0.6932(2) 0.0465(9) Uani 1 1 d . . .
C5 C 0.4692(6) -0.2084(4) 0.6923(2) 0.0521(10) Uani 1 1 d . . .
H5 H 0.3338 -0.2305 0.6841 0.063 Uiso 1 1 calc R . .
C6 C 0.5194(6) -0.0685(4) 0.7033(2) 0.0528(10) Uani 1 1 d . . .
H6 H 0.4169 0.0018 0.7030 0.063 Uiso 1 1 calc R . .
C7 C 0.7798(7) 0.1222(4) 0.7258(2) 0.0596(11) Uani 1 1 d . . .
H7 H 0.9146 0.1114 0.7494 0.071 Uiso 1 1 calc R . .
C8 C 0.8201(5) 0.2194(3) 0.6468(2) 0.0425(9) Uani 1 1 d . . .
C9 C 0.6367(5) 0.2335(4) 0.5934(2) 0.0479(9) Uani 1 1 d . . .
H91 H 0.5971 0.1382 0.5824 0.057 Uiso 1 1 calc R . .
H92 H 0.5220 0.2758 0.6197 0.057 Uiso 1 1 calc R . .
C10 C 0.6847(6) 0.3269(5) 0.5172(2) 0.0654(12) Uani 1 1 d . . .
H101 H 0.7114 0.4247 0.5277 0.078 Uiso 1 1 calc R . .
H102 H 0.5668 0.3299 0.4841 0.078 Uiso 1 1 calc R . .
C11 C 0.8698(7) 0.2689(5) 0.4745(3) 0.0783(14) Uani 1 1 d . . .
H111 H 0.8390 0.1749 0.4592 0.094 Uiso 1 1 calc R . .
H112 H 0.9015 0.3336 0.4279 0.094 Uiso 1 1 calc R . .
C12 C 1.0518(7) 0.2560(5) 0.5271(3) 0.0759(15) Uani 1 1 d . . .
H121 H 1.1667 0.2143 0.5007 0.091 Uiso 1 1 calc R . .
H122 H 1.0904 0.3515 0.5380 0.091 Uiso 1 1 calc R . .
C13 C 1.0056(6) 0.1635(4) 0.6026(2) 0.0550(11) Uani 1 1 d . . .
H131 H 1.1244 0.1606 0.6353 0.066 Uiso 1 1 calc R . .
H132 H 0.9797 0.0656 0.5919 0.066 Uiso 1 1 calc R . .
C14 C 0.6571(8) 0.1953(5) 0.7801(3) 0.0780(14) Uani 1 1 d U . .
H141 H 0.5204 0.2108 0.7600 0.094 Uiso 1 1 calc R . .
H142 H 0.7154 0.2893 0.7837 0.094 Uiso 1 1 calc R . .
C15 C 0.5064(8) 0.1994(5) 0.9058(3) 0.0854(15) Uani 1 1 d U . .
H151 H 0.5855 0.2675 0.9296 0.102 Uiso 1 1 calc R . .
H152 H 0.4352 0.1373 0.9454 0.102 Uiso 1 1 calc R . .
H153 H 0.4092 0.2504 0.8718 0.102 Uiso 1 1 calc R . .
C16 C 0.8299(8) 0.0798(5) 0.9045(3) 0.0901(16) Uani 1 1 d U . .
H161 H 0.8843 -0.0116 0.8926 0.108 Uiso 1 1 calc R . .
H162 H 0.8003 0.0750 0.9593 0.108 Uiso 1 1 calc R . .
H163 H 0.9285 0.1538 0.8896 0.108 Uiso 1 1 calc R . .
C17 C 1.4009(6) -0.2086(4) 0.8921(2) 0.0516(10) Uani 1 1 d . . .
C18 C 1.2847(5) -0.3491(4) 0.8945(3) 0.0582(11) Uani 1 1 d . . .
H181 H 1.3159 -0.3918 0.8471 0.070 Uiso 1 1 calc R . .
H182 H 1.3332 -0.4156 0.9377 0.070 Uiso 1 1 calc R . .
C19 C 1.0560(5) -0.3328(4) 0.9031(2) 0.0523(10) Uani 1 1 d . . .
H191 H 1.0092 -0.2564 0.8644 0.063 Uiso 1 1 calc R . .
H192 H 1.0229 -0.3040 0.9540 0.063 Uiso 1 1 calc R . .
C20 C 0.9425(6) -0.4698(4) 0.8937(2) 0.0502(10) 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
O1 C4 1.376(4) . ?
O1 H1 0.8200 . ?
O2 C8 1.439(4) . ?
O2 H21 0.8200 . ?
N1 C15 1.449(6) . ?
N1 C16 1.468(6) . ?
N1 C14 1.522(6) . ?
N1 H11 0.9100 . ?
O3 C17 1.278(4) . ?
O4 C17 1.223(4) . ?
O5 C20 1.312(4) . ?
O5 H51 1.18(5) . ?
O6 C20 1.214(4) . ?
O7 H71 0.82(4) . ?
O7 H72 0.820(13) . ?
C1 C2 1.378(5) . ?
C1 C6 1.392(5) . ?
C1 C7 1.523(5) . ?
C2 C3 1.374(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(5) . ?
C5 C6 1.386(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C14 1.445(6) . ?
C7 C8 1.569(5) . ?
C7 H7 0.9800 . ?
C8 C9 1.528(5) . ?
C8 C13 1.535(5) . ?
C9 C10 1.523(5) . ?
C9 H91 0.9700 . ?
C9 H92 0.9700 . ?
C10 C11 1.527(6) . ?
C10 H101 0.9700 . ?
C10 H102 0.9700 . ?
C11 C12 1.511(7) . ?
C11 H111 0.9700 . ?
C11 H112 0.9700 . ?
C12 C13 1.507(6) . ?
C12 H121 0.9700 . ?
C12 H122 0.9700 . ?
C13 H131 0.9700 . ?
C13 H132 0.9700 . ?
C14 H141 0.9700 . ?
C14 H142 0.9700 . ?
C15 H151 0.9600 . ?
C15 H152 0.9600 . ?
C15 H153 0.9600 . ?
C16 H161 0.9600 . ?
C16 H162 0.9600 . ?
C16 H163 0.9600 . ?
C17 C18 1.520(5) . ?
C18 C19 1.506(5) . ?
C18 H181 0.9700 . ?
C18 H182 0.9700 . ?
C19 C20 1.514(5) . ?
C19 H191 0.9700 . ?
C19 H192 0.9700 . ?

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
C4 O1 H1 109.5 . . ?
C8 O2 H21 109.5 . . ?
C15 N1 C16 109.2(4) . . ?
C15 N1 C14 105.8(4) . . ?
C16 N1 C14 118.7(4) . . ?
C15 N1 H11 107.6 . . ?
C16 N1 H11 107.6 . . ?
C14 N1 H11 107.6 . . ?
C20 O5 H51 110.3(19) . . ?
H71 O7 H72 109(5) . . ?
C2 C1 C6 117.0(3) . . ?
C2 C1 C7 121.2(4) . . ?
C6 C1 C7 121.9(3) . . ?
C3 C2 C1 122.0(4) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 O1 118.3(3) . . ?
C5 C4 C3 118.7(3) . . ?
O1 C4 C3 123.0(3) . . ?
C4 C5 C6 120.8(4) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 121.0(3) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C14 C7 C1 117.3(3) . . ?
C14 C7 C8 112.4(3) . . ?
C1 C7 C8 112.9(3) . . ?
C14 C7 H7 104.2 . . ?
C1 C7 H7 104.2 . . ?
C8 C7 H7 104.2 . . ?
O2 C8 C9 105.5(3) . . ?
O2 C8 C13 108.8(3) . . ?
C9 C8 C13 109.1(3) . . ?
O2 C8 C7 108.4(3) . . ?
C9 C8 C7 113.8(3) . . ?
C13 C8 C7 111.0(3) . . ?
C10 C9 C8 111.7(3) . . ?
C10 C9 H91 109.3 . . ?
C8 C9 H91 109.3 . . ?
C10 C9 H92 109.3 . . ?
C8 C9 H92 109.3 . . ?
H91 C9 H92 107.9 . . ?
C9 C10 C11 111.7(3) . . ?
C9 C10 H101 109.3 . . ?
C11 C10 H101 109.3 . . ?
C9 C10 H102 109.3 . . ?
C11 C10 H102 109.3 . . ?
H101 C10 H102 107.9 . . ?
C12 C11 C10 109.8(4) . . ?
C12 C11 H111 109.7 . . ?
C10 C11 H111 109.7 . . ?
C12 C11 H112 109.7 . . ?
C10 C11 H112 109.7 . . ?
H111 C11 H112 108.2 . . ?
C13 C12 C11 111.7(3) . . ?
C13 C12 H121 109.3 . . ?
C11 C12 H121 109.3 . . ?
C13 C12 H122 109.3 . . ?
C11 C12 H122 109.3 . . ?
H121 C12 H122 107.9 . . ?
C12 C13 C8 112.5(3) . . ?
C12 C13 H131 109.1 . . ?
C8 C13 H131 109.1 . . ?
C12 C13 H132 109.1 . . ?
C8 C13 H132 109.1 . . ?
H131 C13 H132 107.8 . . ?
C7 C14 N1 113.9(4) . . ?
C7 C14 H141 108.8 . . ?
N1 C14 H141 108.8 . . ?
C7 C14 H142 108.8 . . ?
N1 C14 H142 108.8 . . ?
H141 C14 H142 107.7 . . ?
N1 C15 H151 109.5 . . ?
N1 C15 H152 109.5 . . ?
H151 C15 H152 109.5 . . ?
N1 C15 H153 109.5 . . ?
H151 C15 H153 109.5 . . ?
H152 C15 H153 109.5 . . ?
N1 C16 H161 109.5 . . ?
N1 C16 H162 109.5 . . ?
H161 C16 H162 109.5 . . ?
N1 C16 H163 109.5 . . ?
H161 C16 H163 109.5 . . ?
H162 C16 H163 109.5 . . ?
O4 C17 O3 121.3(4) . . ?
O4 C17 C18 120.7(4) . . ?
O3 C17 C18 118.0(4) . . ?
C19 C18 C17 114.4(3) . . ?
C19 C18 H181 108.7 . . ?
C17 C18 H181 108.7 . . ?
C19 C18 H182 108.7 . . ?
C17 C18 H182 108.7 . . ?
H181 C18 H182 107.6 . . ?
C18 C19 C20 113.2(3) . . ?
C18 C19 H191 108.9 . . ?
C20 C19 H191 108.9 . . ?
C18 C19 H192 108.9 . . ?
C20 C19 H192 108.9 . . ?
H191 C19 H192 107.8 . . ?
O6 C20 O5 121.5(3) . . ?
O6 C20 C19 123.1(4) . . ?
O5 C20 C19 115.4(4) . . ?

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         0.776
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.054


