# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Ulrich J Griesser'
_publ_contact_author_email       ULRICH.GRIESSER@UIBK.AC.AT

_publ_section_title              
;
Structural Characterisation and desolvation behaviour
of four Solvates of R-Cinacalcet Hydrochloride
;
_publ_requested_category         FO
loop_
_publ_author_name
'Ulrich J Griesser'
'Doris E. Braun'
'Thomas Gelbrich'
'Volker Kahlenberg'
'Johannes Ludescher'

# Attachment 'B809219B_Braun_CCCHC_S_AC_revised.cif'

data_free
_database_code_depnum_ccdc_archive 'CCDC 690028'
#\#CIF_1.1

# CIF produced by WinGX routine CIF_UPDATE
# Created on 2007-10-05 at 08:07:40
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.3
# Request file : d:\programme\wingx\files\archive.dat
# CIF files read : free messung

_audit_creation_date             2007-10-05T08:07:40-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_name_common            'Cinacalcet HCl acetic acid solvate'
_chemical_formula_sum            'C24 H27 Cl F3 N O2'
_chemical_formula_moiety         'C24 H27 Cl F3 N O2'
_chemical_formula_weight         453.92
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.5434(8)
_cell_length_b                   18.575(2)
_cell_length_c                   16.7756(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2350.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9331
_cell_measurement_theta_min      1.64
_cell_measurement_theta_max      24.68

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       'fragment of a lath'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7999
_exptl_absorpt_correction_T_max  0.9757
_exptl_absorpt_process_details   
;
Bruker SADABS program multi-scan V2.03
R.H. Blessing, Acta Cryst. (1995) A51 33-38
;

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_number            13752
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         24.68
_diffrn_reflns_theta_full        24.68
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_reflns_number_total             3944
_reflns_number_gt                3393
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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)+(0.0299P)²+0.6428P] 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_number_reflns         3944
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.0845
_refine_ls_wR_factor_gt          0.0807
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_restrained_S_all      1.07
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(7)
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.037

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Cl1 Cl 0.84810(9) 0.22270(4) 0.90793(4) 0.03196(16) Uani 1 1 d . . .
F1 F -0.3134(6) -0.0465(2) 1.0666(5) 0.117(2) Uani 0.789(9) 1 d P A 1
F2 F -0.1973(5) -0.14668(18) 1.0371(3) 0.0897(16) Uani 0.789(9) 1 d P A 1
F3 F -0.2688(6) -0.1288(4) 1.1559(2) 0.120(3) Uani 0.789(9) 1 d P A 1
F4 F -0.3106(18) -0.0738(9) 1.1624(8) 0.074(4) Uiso 0.211(9) 1 d P A 2
F5 F -0.298(2) -0.0659(8) 1.0427(8) 0.053(4) Uiso 0.211(9) 1 d P A 2
F6 F -0.2215(18) -0.1572(7) 1.0894(12) 0.077(5) Uiso 0.211(9) 1 d P A 2
N1 N 0.2668(3) 0.23236(11) 0.91649(14) 0.0279(5) Uani 1 1 d . . .
H2B H 0.156(4) 0.2309(15) 0.9038(17) 0.037(8) Uiso 1 1 d . . .
H1A H 0.279(4) 0.2475(15) 0.9706(19) 0.045(9) Uiso 1 1 d . . .
C2 C 0.3606(4) 0.28607(13) 0.86522(15) 0.0309(6) Uani 1 1 d . . .
H2A H 0.4894 0.285 0.8792 0.037 Uiso 1 1 calc R . .
C3 C 0.3424(4) 0.27000(14) 0.77654(14) 0.0294(6) Uani 1 1 d . . .
C4 C 0.1940(4) 0.23881(15) 0.74595(16) 0.0369(7) Uani 1 1 d . . .
H4A H 0.1026 0.2237 0.7811 0.044 Uiso 1 1 calc R . .
C5 C 0.1727(5) 0.22837(17) 0.66300(16) 0.0460(7) Uani 1 1 d . . .
H5A H 0.0688 0.2057 0.6431 0.055 Uiso 1 1 calc R . .
C6 C 0.2998(5) 0.25051(15) 0.61223(17) 0.0443(8) Uani 1 1 d . . .
H6A H 0.2844 0.2431 0.5566 0.053 Uiso 1 1 calc R . .
C7 C 0.5842(5) 0.31093(17) 0.5869(2) 0.0485(8) Uani 1 1 d . . .
H7A H 0.5671 0.3049 0.5312 0.058 Uiso 1 1 calc R . .
C8 C 0.7315(5) 0.34462(19) 0.6131(2) 0.0560(10) Uani 1 1 d . . .
H8A H 0.8167 0.362 0.5762 0.067 Uiso 1 1 calc R . .
C9 C 0.7583(5) 0.35387(18) 0.6954(2) 0.0530(9) Uani 1 1 d . . .
H9A H 0.8623 0.3773 0.7139 0.064 Uiso 1 1 calc R . .
C10 C 0.6362(4) 0.32948(16) 0.74861(19) 0.0397(7) Uani 1 1 d . . .
H10A H 0.6566 0.3364 0.804 0.048 Uiso 1 1 calc R . .
C11 C 0.4802(4) 0.29420(14) 0.72378(16) 0.0308(7) Uani 1 1 d . . .
C12 C 0.4554(4) 0.28455(15) 0.63991(16) 0.0354(7) Uani 1 1 d . . .
C13 C 0.2884(5) 0.36036(14) 0.88578(18) 0.0445(9) Uani 1 1 d . . .
H13A H 0.3026 0.3691 0.943 0.067 Uiso 1 1 calc R . .
H13B H 0.1624 0.3627 0.8718 0.067 Uiso 1 1 calc R . .
H13C H 0.3537 0.397 0.8558 0.067 Uiso 1 1 calc R . .
C14 C 0.3356(4) 0.15690(13) 0.91542(17) 0.0343(6) Uani 1 1 d . . .
H14A H 0.4656 0.1572 0.9238 0.041 Uiso 1 1 calc R . .
H14B H 0.3112 0.1347 0.8629 0.041 Uiso 1 1 calc R . .
C15 C 0.2475(4) 0.11344(13) 0.98034(17) 0.0316(6) Uani 1 1 d . . .
H15A H 0.119 0.1103 0.9689 0.038 Uiso 1 1 calc R . .
H15B H 0.2619 0.139 1.0317 0.038 Uiso 1 1 calc R . .
C16 C 0.3217(5) 0.03736(14) 0.98891(18) 0.0411(8) Uani 1 1 d . . .
H16A H 0.3024 0.0103 0.9388 0.049 Uiso 1 1 calc R . .
H16B H 0.4509 0.0397 0.999 0.049 Uiso 1 1 calc R . .
C17 C 0.2312(4) -0.00123(14) 1.05719(18) 0.0346(7) Uani 1 1 d . . .
C18 C 0.0661(4) -0.03213(14) 1.04608(17) 0.0343(7) Uani 1 1 d . . .
H18A H 0.0127 -0.0314 0.9948 0.041 Uiso 1 1 calc R . .
C19 C -0.0223(4) -0.06437(14) 1.10974(18) 0.0360(7) Uani 1 1 d . A .
C20 C 0.0527(5) -0.06609(16) 1.18445(19) 0.0437(8) Uani 1 1 d . . .
H20A H -0.0078 -0.0885 1.2275 0.052 Uiso 1 1 calc R . .
C21 C 0.2168(5) -0.03486(17) 1.1963(2) 0.0493(9) Uani 1 1 d . . .
H21A H 0.2696 -0.0352 1.2477 0.059 Uiso 1 1 calc R . .
C22 C 0.3039(5) -0.00301(16) 1.13261(19) 0.0431(8) Uani 1 1 d . . .
H22A H 0.4169 0.0182 1.1412 0.052 Uiso 1 1 calc R . .
C23 C -0.2020(5) -0.09531(17) 1.0956(3) 0.0564(9) Uani 1 1 d . . .
O2S O 0.7119(3) 0.07394(11) 0.86082(16) 0.0539(6) Uani 1 1 d . . .
H2S H 0.7687 0.1128 0.8625 0.081 Uiso 1 1 calc R . .
O1S O 0.9811(3) 0.02753(13) 0.84746(16) 0.0563(6) Uani 1 1 d . . .
C2S C 0.8227(5) 0.02007(16) 0.84657(18) 0.0388(7) Uani 1 1 d . . .
C1S C 0.7288(5) -0.04924(17) 0.8320(2) 0.0593(10) Uani 1 1 d . . .
H1SA H 0.8152 -0.0864 0.8176 0.089 Uiso 1 1 calc R . .
H1SB H 0.6437 -0.0431 0.7883 0.089 Uiso 1 1 calc R . .
H1SC H 0.6656 -0.0638 0.8804 0.089 Uiso 1 1 calc R . .


#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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
F1 C23 1.328(5) . ?
F2 C23 1.370(5) . ?
F3 C23 1.289(5) . ?
F4 C23 1.444(13) . ?
F5 C23 1.271(16) . ?
F6 C23 1.164(13) . ?
N1 C14 1.495(3) . ?
N1 C2 1.495(3) . ?
C2 C13 1.523(4) . ?
C2 C3 1.523(3) . ?
C3 C4 1.361(4) . ?
C3 C11 1.437(4) . ?
C4 C5 1.414(4) . ?
C5 C6 1.346(4) . ?
C6 C12 1.412(4) . ?
C7 C8 1.349(5) . ?
C7 C12 1.405(4) . ?
C8 C9 1.405(5) . ?
C9 C10 1.361(4) . ?
C10 C11 1.410(4) . ?
C11 C12 1.431(4) . ?
C14 C15 1.510(4) . ?
C15 C16 1.527(4) . ?
C16 C17 1.514(4) . ?
C17 C22 1.380(4) . ?
C17 C18 1.384(4) . ?
C18 C19 1.394(4) . ?
C19 C20 1.375(4) . ?
C19 C23 1.491(5) . ?
C20 C21 1.382(5) . ?
C21 C22 1.387(5) . ?
O2S C2S 1.325(4) . ?
O1S C2S 1.203(4) . ?
C2S C1S 1.490(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 N1 C2 117.0(2) . . ?
N1 C2 C13 107.8(2) . . ?
N1 C2 C3 112.8(2) . . ?
C13 C2 C3 111.5(2) . . ?
C4 C3 C11 119.7(2) . . ?
C4 C3 C2 121.7(3) . . ?
C11 C3 C2 118.3(2) . . ?
C3 C4 C5 121.5(3) . . ?
C6 C5 C4 120.0(3) . . ?
C5 C6 C12 121.4(3) . . ?
C8 C7 C12 121.6(3) . . ?
C7 C8 C9 119.7(3) . . ?
C10 C9 C8 120.4(3) . . ?
C9 C10 C11 121.7(3) . . ?
C10 C11 C12 117.3(3) . . ?
C10 C11 C3 124.5(3) . . ?
C12 C11 C3 118.1(3) . . ?
C7 C12 C6 121.5(3) . . ?
C7 C12 C11 119.2(3) . . ?
C6 C12 C11 119.2(3) . . ?
N1 C14 C15 109.9(2) . . ?
C14 C15 C16 113.7(2) . . ?
C17 C16 C15 110.2(2) . . ?
C22 C17 C18 118.1(3) . . ?
C22 C17 C16 121.7(3) . . ?
C18 C17 C16 120.0(3) . . ?
C17 C18 C19 120.4(3) . . ?
C20 C19 C18 120.7(3) . . ?
C20 C19 C23 120.6(3) . . ?
C18 C19 C23 118.6(3) . . ?
C19 C20 C21 119.3(3) . . ?
C20 C21 C22 119.5(3) . . ?
C17 C22 C21 121.9(3) . . ?
F6 C23 F5 106.8(11) . . ?
F6 C23 F3 62.9(9) . . ?
F5 C23 F3 122.1(8) . . ?
F6 C23 F1 124.1(8) . . ?
F5 C23 F1 24.3(6) . . ?
F3 C23 F1 111.6(5) . . ?
F6 C23 F2 41.4(9) . . ?
F5 C23 F2 79.3(7) . . ?
F3 C23 F2 103.6(3) . . ?
F1 C23 F2 103.2(4) . . ?
F6 C23 F4 105.7(10) . . ?
F5 C23 F4 95.7(8) . . ?
F3 C23 F4 45.8(5) . . ?
F1 C23 F4 74.7(6) . . ?
F2 C23 F4 139.7(7) . . ?
F6 C23 C19 120.7(8) . . ?
F5 C23 C19 117.7(8) . . ?
F3 C23 C19 114.6(3) . . ?
F1 C23 C19 111.8(3) . . ?
F2 C23 C19 111.0(3) . . ?
F4 C23 C19 106.6(7) . . ?
O1S C2S O2S 122.5(3) . . ?
O1S C2S C1S 125.0(3) . . ?
O2S C2S C1S 112.5(3) . . ?

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 N1 C2 C13 -171.0(2) . . . . ?
C14 N1 C2 C3 65.5(3) . . . . ?
N1 C2 C3 C4 32.6(4) . . . . ?
C13 C2 C3 C4 -88.9(3) . . . . ?
N1 C2 C3 C11 -152.7(2) . . . . ?
C13 C2 C3 C11 85.8(3) . . . . ?
C11 C3 C4 C5 1.1(4) . . . . ?
C2 C3 C4 C5 175.7(3) . . . . ?
C3 C4 C5 C6 -1.0(5) . . . . ?
C4 C5 C6 C12 -0.3(5) . . . . ?
C12 C7 C8 C9 0.0(5) . . . . ?
C7 C8 C9 C10 -0.4(5) . . . . ?
C8 C9 C10 C11 0.2(5) . . . . ?
C9 C10 C11 C12 0.4(4) . . . . ?
C9 C10 C11 C3 -177.1(3) . . . . ?
C4 C3 C11 C10 177.6(3) . . . . ?
C2 C3 C11 C10 2.8(4) . . . . ?
C4 C3 C11 C12 0.1(4) . . . . ?
C2 C3 C11 C12 -174.7(2) . . . . ?
C8 C7 C12 C6 178.8(3) . . . . ?
C8 C7 C12 C11 0.6(5) . . . . ?
C5 C6 C12 C7 -176.8(3) . . . . ?
C5 C6 C12 C11 1.4(4) . . . . ?
C10 C11 C12 C7 -0.7(4) . . . . ?
C3 C11 C12 C7 176.9(3) . . . . ?
C10 C11 C12 C6 -179.0(3) . . . . ?
C3 C11 C12 C6 -1.4(4) . . . . ?
C2 N1 C14 C15 170.2(2) . . . . ?
N1 C14 C15 C16 -174.7(3) . . . . ?
C14 C15 C16 C17 177.8(3) . . . . ?
C15 C16 C17 C22 -95.2(3) . . . . ?
C15 C16 C17 C18 80.7(3) . . . . ?
C22 C17 C18 C19 -0.4(4) . . . . ?
C16 C17 C18 C19 -176.5(3) . . . . ?
C17 C18 C19 C20 0.0(4) . . . . ?
C17 C18 C19 C23 178.4(3) . . . . ?
C18 C19 C20 C21 0.6(5) . . . . ?
C23 C19 C20 C21 -177.8(3) . . . . ?
C19 C20 C21 C22 -0.7(5) . . . . ?
C18 C17 C22 C21 0.3(4) . . . . ?
C16 C17 C22 C21 176.4(3) . . . . ?
C20 C21 C22 C17 0.2(5) . . . . ?
C20 C19 C23 F6 -78.4(13) . . . . ?
C18 C19 C23 F6 103.1(13) . . . . ?
C20 C19 C23 F5 147.8(8) . . . . ?
C18 C19 C23 F5 -30.6(9) . . . . ?
C20 C19 C23 F3 -6.5(6) . . . . ?
C18 C19 C23 F3 175.1(5) . . . . ?
C20 C19 C23 F1 121.8(5) . . . . ?
C18 C19 C23 F1 -56.6(6) . . . . ?
C20 C19 C23 F2 -123.5(4) . . . . ?
C18 C19 C23 F2 58.0(4) . . . . ?
C20 C19 C23 F4 42.0(7) . . . . ?
C18 C19 C23 F4 -136.5(7) . . . . ?


