#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:44:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180353 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/22/7202280.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7202280
loop_
_publ_author_name
'Braun, Doris E.'
'Kahlenberg, Volker'
'Gelbrich, Thomas'
'Ludescher, Johannes'
'Griesser, Ulrich J.'
_publ_section_title
;
 Solid state characterisation of four solvates of R-cinacalcet
 hydrochloride
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              1617
_journal_paper_doi               10.1039/b809219b
_journal_volume                  10
_journal_year                    2008
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C24 H27 Cl F3 N O2'
_chemical_formula_sum            'C24 H27 Cl F3 N O2'
_chemical_formula_weight         453.92
_chemical_name_common            'Cinacalcet HCl acetic acid solvate'
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2007-10-05T08:07:40-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5434(8)
_cell_length_b                   18.575(2)
_cell_length_c                   16.7756(19)
_cell_measurement_reflns_used    9331
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.68
_cell_measurement_theta_min      1.64
_cell_volume                     2350.6(4)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13752
_diffrn_reflns_theta_full        24.68
_diffrn_reflns_theta_max         24.68
_diffrn_reflns_theta_min         1.64
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  0.9757
_exptl_absorpt_correction_T_min  0.7999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker SADABS program multi-scan V2.03
R.H. Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'fragment of a lath'
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         3944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.07
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0458
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0299P)²+0.6428P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0845
_reflns_number_gt                3393
_reflns_number_total             3944
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b809219b.txt
_cod_data_source_block           free
_cod_database_code               7202280
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'
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 . .
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_
_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_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_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) . . . . ?
