#------------------------------------------------------------------------------
#$Date: 2017-11-23 10:39:03 +0200 (Thu, 23 Nov 2017) $
#$Revision: 203477 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/81/1548159.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_1548159
loop_
_publ_author_name
'M. A. Neumann'
'J. van de Streek'
'F. P. A. Fabbiani'
'P. Hidber'
'O. Grassmann'
_publ_section_title
;
 Combined crystal structure prediction and high-pressure crystallization
 in rational pharmaceutical polymorph screening
;
_journal_name_full               'Nature Communications'
_journal_page_first              7793
_journal_paper_doi               10.1038/ncomms8793
_journal_volume                  6
_journal_year                    2015
_chemical_formula_moiety         'C23 H35 N O2 S'
_chemical_formula_sum            'C23 H35 N O2 S'
_chemical_formula_weight         389.58
_chemical_name_common            Dalcetrapib
_chemical_name_systematic
;
S-[2-({[1-(2-ethylbutyl)cyclohexyl]carbonyl}amino)phenyl] 2-methylpropanethioate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     'known structure'
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 88.7400(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2235(3)
_cell_length_b                   9.8526(2)
_cell_length_c                   20.7922(5)
_cell_measurement_reflns_used    6329
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.99
_cell_measurement_theta_min      2.64
_cell_volume                     2298.66(9)
_computing_cell_refinement       'APEX2 v2012.4-0'
_computing_data_collection       'APEX2 v2012.4-0'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    Sir92
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.936
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.936
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17030
_diffrn_reflns_point_group_measured_fraction_full 0.936
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.718
_diffrn_reflns_theta_min         1.815
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.8619
_exptl_absorpt_correction_T_min  0.7919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (Sheldrick, 2012a)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.126
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0057(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3894
_refine_ls_number_restraints     119
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0794P)²+0.9076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1564
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3112
_reflns_number_total             3894
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ncomms8793-s3.cif
_cod_data_source_block           FormA_RT
_cod_database_code               1548159
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.27030(5) 0.67054(6) 0.15912(3) 0.0633(2) Uani 1 1 d D . . . .
O2 O 0.44334(15) 0.74318(14) 0.26492(7) 0.0593(4) Uani 1 1 d D . . . .
O3 O 0.2049(2) 0.5206(3) 0.06079(13) 0.1273(10) Uani 1 1 d D . . . .
N4 N 0.47273(16) 0.53054(16) 0.22897(8) 0.0498(4) Uani 1 1 d D . . . .
H4 H 0.4725 0.4456 0.2386 0.060 Uiso 1 1 calc R U . . .
C7 C 0.0439(3) 0.6143(5) 0.1241(2) 0.1272(15) Uani 1 1 d D . . . .
H7A H 0.0420 0.6703 0.1630 0.153 Uiso 1 1 calc R U . . .
C5 C -0.0138(5) 0.6930(7) 0.0718(3) 0.207(3) Uani 1 1 d D . . . .
H5A H 0.0319 0.7734 0.0627 0.311 Uiso 1 1 calc R U . . .
H5B H -0.0931 0.7182 0.0855 0.311 Uiso 1 1 calc R U . . .
H5C H -0.0174 0.6381 0.0338 0.311 Uiso 1 1 calc R U . . .
C6 C -0.0159(5) 0.4805(6) 0.1401(4) 0.254(4) Uani 1 1 d D . . . .
H6A H -0.0488 0.4426 0.1018 0.380 Uiso 1 1 calc R U . . .
H6B H -0.0785 0.4951 0.1715 0.380 Uiso 1 1 calc R U . . .
H6C H 0.0417 0.4188 0.1571 0.380 Uiso 1 1 calc R U . . .
C8 C 0.1736(3) 0.5876(3) 0.10585(15) 0.0870(9) Uani 1 1 d D . . . .
C9 C 0.41269(19) 0.6315(2) 0.12655(10) 0.0502(5) Uani 1 1 d D . . . .
C10 C 0.4419(2) 0.6662(2) 0.06313(11) 0.0591(6) Uani 1 1 d D . . . .
H10 H 0.3866 0.7116 0.0384 0.071 Uiso 1 1 calc R U . . .
C11 C 0.5516(2) 0.6337(2) 0.03693(11) 0.0649(6) Uani 1 1 d D . . . .
H11 H 0.5700 0.6561 -0.0056 0.078 Uiso 1 1 calc R U . . .
C12 C 0.6343(2) 0.5683(3) 0.07344(12) 0.0654(6) Uani 1 1 d D . . . .
H12 H 0.7081 0.5451 0.0555 0.079 Uiso 1 1 calc R U . . .
C13 C 0.6077(2) 0.5371(2) 0.13699(11) 0.0579(6) Uani 1 1 d D . . . .
H13 H 0.6647 0.4947 0.1618 0.069 Uiso 1 1 calc R U . . .
C14 C 0.49728(19) 0.56798(19) 0.16399(9) 0.0467(5) Uani 1 1 d D . . . .
C15 C 0.44965(19) 0.62133(19) 0.27655(10) 0.0484(5) Uani 1 1 d D . . . .
C16 C 0.4351(2) 0.5635(2) 0.34458(10) 0.0572(6) Uani 1 1 d D U . . .
C17 C 0.3772(3) 0.6685(3) 0.38887(12) 0.0753(7) Uani 1 1 d D U . . .
H17A H 0.3810 0.6364 0.4329 0.090 Uiso 1 1 calc R U . . .
H17B H 0.4227 0.7521 0.3859 0.090 Uiso 1 1 calc R U . . .
C18 C 0.2504(3) 0.6987(4) 0.37417(17) 0.0994(10) Uani 1 1 d D U . . .
H18A H 0.2472 0.7435 0.3327 0.119 Uiso 1 1 calc R U . . .
H18B H 0.2181 0.7605 0.4064 0.119 Uiso 1 1 calc R U . . .
C19 C 0.1739(3) 0.5713(5) 0.3728(2) 0.1209(13) Uani 1 1 d D U . . .
H19A H 0.1663 0.5342 0.4160 0.145 Uiso 1 1 calc R U . . .
H19B H 0.0948 0.5945 0.3585 0.145 Uiso 1 1 calc R U . . .
C20 C 0.2278(3) 0.4657(4) 0.32845(18) 0.1048(11) Uani 1 1 d D U . . .
H20A H 0.2253 0.4981 0.2845 0.126 Uiso 1 1 calc R U . . .
H20B H 0.1809 0.3831 0.3314 0.126 Uiso 1 1 calc R U . . .
C21 C 0.3561(3) 0.4344(3) 0.34527(13) 0.0777(8) Uani 1 1 d D U . . .
H21A H 0.3887 0.3693 0.3146 0.093 Uiso 1 1 calc R U . . .
H21B H 0.3576 0.3934 0.3877 0.093 Uiso 1 1 calc R U . . .
C22 C 0.5583(3) 0.5167(3) 0.36898(13) 0.0736(7) Uani 1 1 d D . . . .
H22A H 0.5452 0.4723 0.4102 0.088 Uiso 1 1 calc R U . A 1
H22B H 0.5889 0.4485 0.3393 0.088 Uiso 1 1 calc R U . A 1
C23A C 0.6550(3) 0.6221(3) 0.37731(14) 0.0869(8) Uani 0.6 1 d D U P B 1
H23A H 0.6180 0.7022 0.3972 0.104 Uiso 0.6 1 calc R U P B 1
C24A C 0.7255(8) 0.6698(12) 0.3176(4) 0.118(4) Uani 0.6 1 d D U P B 1
H24A H 0.6700 0.7040 0.2864 0.142 Uiso 0.6 1 calc R U P B 1
H24B H 0.7768 0.7444 0.3297 0.142 Uiso 0.6 1 calc R U P B 1
C26A C 0.7345(7) 0.5547(7) 0.4281(3) 0.099(2) Uani 0.6 1 d D U P B 1
H26A H 0.6845 0.5254 0.4642 0.118 Uiso 0.6 1 calc R U P B 1
H26B H 0.7714 0.4745 0.4094 0.118 Uiso 0.6 1 calc R U P B 1
C25A C 0.8008(8) 0.5613(10) 0.2863(4) 0.158(3) Uani 0.6 1 d D U P B 1
H25A H 0.8392 0.5972 0.2482 0.237 Uiso 0.6 1 calc R U P B 1
H25B H 0.7512 0.4860 0.2748 0.237 Uiso 0.6 1 calc R U P B 1
H25C H 0.8601 0.5313 0.3157 0.237 Uiso 0.6 1 calc R U P B 1
C27A C 0.8297(6) 0.6451(7) 0.4526(3) 0.116(2) Uani 0.6 1 d D U P B 1
H27A H 0.8638 0.6051 0.4900 0.174 Uiso 0.6 1 calc R U P B 1
H27B H 0.7961 0.7319 0.4636 0.174 Uiso 0.6 1 calc R U P B 1
H27C H 0.8905 0.6565 0.4199 0.174 Uiso 0.6 1 calc R U P B 1
C23B C 0.6550(3) 0.6221(3) 0.37731(14) 0.0869(8) Uani 0.4 1 d D U P B 2
H23B H 0.6127 0.7089 0.3801 0.104 Uiso 0.4 1 calc R U P B 2
C24B C 0.7288(11) 0.6297(16) 0.3136(4) 0.095(4) Uani 0.4 1 d D U P B 2
H24C H 0.7661 0.5420 0.3067 0.114 Uiso 0.4 1 calc R U P B 2
H24D H 0.6735 0.6432 0.2790 0.114 Uiso 0.4 1 calc R U P B 2
C26B C 0.7367(10) 0.6206(11) 0.4360(4) 0.099(4) Uani 0.4 1 d D U P B 2
H26C H 0.7836 0.7032 0.4360 0.119 Uiso 0.4 1 calc R U P B 2
H26D H 0.6875 0.6200 0.4750 0.119 Uiso 0.4 1 calc R U P B 2
C25B C 0.8246(10) 0.7365(13) 0.3071(6) 0.154(4) Uani 0.4 1 d D U P B 2
H25D H 0.8544 0.7386 0.2635 0.230 Uiso 0.4 1 calc R U P B 2
H25E H 0.8885 0.7153 0.3353 0.230 Uiso 0.4 1 calc R U P B 2
H25F H 0.7919 0.8236 0.3183 0.230 Uiso 0.4 1 calc R U P B 2
C27B C 0.8187(9) 0.5019(10) 0.4371(5) 0.119(3) Uani 0.4 1 d D U P B 2
H27D H 0.8458 0.4881 0.4801 0.179 Uiso 0.4 1 calc R U P B 2
H27E H 0.8860 0.5187 0.4089 0.179 Uiso 0.4 1 calc R U P B 2
H27F H 0.7774 0.4223 0.4230 0.179 Uiso 0.4 1 calc R U P B 2
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'
S S 0.1246 0.1234 '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
C9 S1 C8 102.85(12) . .
C15 N4 C14 123.55(16) . .
C5 C7 C6 114.5(5) . .
C5 C7 C8 109.7(4) . .
C6 C7 C8 108.8(4) . .
O3 C8 C7 123.8(3) . .
O3 C8 S1 125.0(2) . .
C7 C8 S1 111.2(2) . .
C14 C9 C10 119.4(2) . .
C14 C9 S1 120.48(16) . .
C10 C9 S1 120.13(18) . .
C11 C10 C9 120.5(2) . .
C12 C11 C10 120.1(2) . .
C11 C12 C13 119.9(2) . .
C12 C13 C14 120.8(2) . .
C13 C14 C9 119.26(19) . .
C13 C14 N4 118.80(19) . .
C9 C14 N4 121.92(18) . .
O2 C15 N4 120.87(18) . .
O2 C15 C16 122.76(18) . .
N4 C15 C16 116.35(17) . .
C17 C16 C15 109.97(18) . .
C17 C16 C21 108.4(2) . .
C15 C16 C21 111.33(19) . .
C17 C16 C22 112.1(2) . .
C15 C16 C22 109.54(19) . .
C21 C16 C22 105.5(2) . .
C18 C17 C16 114.1(2) . .
C17 C18 C19 112.4(3) . .
C20 C19 C18 111.2(3) . .
C19 C20 C21 111.6(3) . .
C20 C21 C16 112.1(2) . .
C23A C22 C16 118.7(2) . .
C22 C23A C24A 118.4(5) . .
C22 C23A C26A 102.1(3) . .
C24A C23A C26A 113.0(4) . .
C25A C24A C23A 114.1(7) . .
C27A C26A C23A 113.9(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C9 1.764(2) .
S1 C8 1.768(3) .
O2 C15 1.227(2) .
O3 C8 1.193(3) .
N4 C15 1.355(3) .
N4 C14 1.422(3) .
C7 C5 1.494(7) .
C7 C6 1.514(4) .
C7 C8 1.519(4) .
C9 C14 1.390(3) .
C9 C10 1.394(3) .
C10 C11 1.374(3) .
C11 C12 1.372(4) .
C12 C13 1.383(3) .
C13 C14 1.383(3) .
C15 C16 1.530(3) .
C16 C17 1.522(3) .
C16 C21 1.550(3) .
C16 C22 1.554(4) .
C17 C18 1.491(4) .
C18 C19 1.521(5) .
C19 C20 1.508(5) .
C20 C21 1.521(5) .
C22 C23A 1.515(4) .
C23A C24A 1.531(4) .
C23A C26A 1.548(5) .
C24A C25A 1.502(10) .
C26A C27A 1.488(7) .
C24B C25B 1.509(10) .
C26B C27B 1.489(7) .
