data_FormA_223K
 
_audit_creation_method            SHELXL-2013
_chemical_name_systematic
;
S-[2-({[1-(2-ethylbutyl)cyclohexyl]carbonyl}amino)phenyl] 2-methylpropanethioate 
;
_chemical_name_common             Dalcetrapib
_chemical_melting_point           ?
_chemical_formula_moiety          
'C23 H35 N O2 S'
_chemical_formula_sum
 'C23 H35 N O2 S' 
_chemical_formula_weight          389.58

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'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_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'
 
_cell_length_a                    11.181(15)
_cell_length_b                    9.809(13)
_cell_length_c                    20.71(3)
_cell_angle_alpha                 90
_cell_angle_beta                  88.545(13)
_cell_angle_gamma                 90
_cell_volume                      2270(5)
_cell_formula_units_Z             4
_cell_measurement_temperature     223(2)
_cell_measurement_reflns_used     1457 
_cell_measurement_theta_min       3.41 
_cell_measurement_theta_max       20.21 
 
_exptl_crystal_description        block 
_exptl_crystal_colour             colourless  
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ?              
_exptl_crystal_density_diffrn     1.140          
_exptl_crystal_F_000              848
_exptl_crystal_size_max           0.50 
_exptl_crystal_size_mid           0.30 
_exptl_crystal_size_min           0.20 
_exptl_absorpt_coefficient_mu     0.159
_exptl_absorpt_correction_T_min   0.5711
_exptl_absorpt_correction_T_max   0.8618   
_exptl_absorpt_process_details   
;
SADABS (Sheldrick, 2012<i>a</i>)
;
 
_exptl_special_details
;
Form A measured at 223 K
;
 
_diffrn_ambient_temperature       223(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 APEXII CCD area-detector'
_diffrn_measurement_method        '\w and \f scans' 
_diffrn_reflns_number             7275
_diffrn_reflns_av_unetI/netI      0.0664
_diffrn_reflns_av_R_equivalents   0.0648
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -7
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -20
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          3.366
_diffrn_reflns_theta_max          21.004
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.988
_diffrn_measured_fraction_theta_full  0.584
_diffrn_reflns_Laue_measured_fraction_max    0.988
_diffrn_reflns_Laue_measured_fraction_full   0.584
_diffrn_reflns_point_group_measured_fraction_max   0.988
_diffrn_reflns_point_group_measured_fraction_full  0.584
_reflns_number_total              2399
_reflns_number_gt                 1798
_reflns_threshold_expression      'I > 2\s(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_refine_special_details
;
Refinement of F^2^ against ALL reflections. 
All non-H-atoms were refined with anisotropic thermal parameters.
Hydrogen atoms were placed in idealised positions and refined using a
riding model.
Site occupancy factors for disorderd groups were first refined and later
fixed to the refined values.
The newly implemented RIGU restraints were used during refinement.
Bond-distances and bond-angle restraints were also used during refinement.

The following is the output of checkCIF/PLATON routine on the .cif and .fcf
files:

THETM01_ALERT_3_A  The value of sine(theta_max)/wavelength is less than 0.550
            Calculated sin(theta_max)/wavelength =    0.5043
PLAT019_ALERT_1_B Check _diffrn_measured_fraction_theta_full/_max       0.591    
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 10 for a
            centrosymmetric structure
            sine(theta)/lambda                0.5043
            Proportion of unique data used    1.0000
            Ratio reflections to parameters   8.5071
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................   8.61 
PLAT148_ALERT_3_C su on the      a  - Axis is (Too) Large ........  0.015 Ang.
PLAT148_ALERT_3_C su on the      b  - Axis is (Too) Large ........  0.0130 Ang.  
PLAT148_ALERT_3_C su on the      c  - Axis is (Too) Large ........  0.030 Ang. 
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............  0.0060 Ang. 
Upon cooling and during the data collection the crystal splits into several
fragments. Reflections get progressively broader with more domains building
into the diffraction. The structure presented here comes from one major domain
that survives for three of the five runs collected, with satisfactory crystal
centring. Several cooling experiments were attempted in order to improve data
quality - the data presented here is the best we could do using a home source.


PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ... 5.5 Ratio 
PLAT222_ALERT_3_C Large Non-Solvent    H    Uiso(max)/Uiso(min) .. 6.3 Ratio 
PLAT242_ALERT_2_C Low       Ueq as Compared to Neighbors for ..... C7 Check 
PLAT242_ALERT_2_C Low       Ueq as Compared to Neighbors for ..... C8 Check 
The structure is disordered. Please also see comments above.

 
PLAT157_ALERT_4_C Non-standard Monoclinic Beta Angle less 90 Deg     88.54 Deg. 
This angle has been chosen to allow direct structural comparison with 
the low-temperature polymorph.

  
PLAT413_ALERT_2_B Short Inter XH3 .. XHn     H6B    ..  H25A    .. 1.91 Ang.
PLAT413_ALERT_2_C Short Inter XH3 .. XHn     H19B   ..  H27D    .. 2.14 Ang.  
PLAT414_ALERT_2_C Short Intra D-H..H-X       H4     ..  H21A    .. 1.98 Ang.
Noted, no action taken. These distances are not exceedingly short.
Some of these atoms are disorderd; it is possible that
this distance is an artifact of refinement. H-atoms were placed in 
calculated positions.  
;
 
_computing_data_collection        'APEX2 v2012.4-0'
_computing_cell_refinement        'APEX2 v2012.4-0'
_computing_data_reduction         'SAINT (Bruker, 2007)' 
_computing_structure_solution     'known structures' 
_computing_structure_refinement   'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0664P)^2^+0.8362P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary      'known structure'
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          2399
_refine_ls_number_parameters      282
_refine_ls_number_restraints      278
_refine_ls_R_factor_all           0.0719
_refine_ls_R_factor_gt            0.0500
_refine_ls_wR_factor_ref          0.1397
_refine_ls_wR_factor_gt           0.1254
_refine_ls_goodness_of_fit_ref    1.028
_refine_ls_restrained_S_all       1.068
_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_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 0.26898(8) 0.67215(10) 0.15976(4) 0.0520(4) Uani 1 1 d D U . . .
O2 O 0.4416(2) 0.7421(2) 0.26579(10) 0.0493(7) Uani 1 1 d D U . . .
O3 O 0.2014(2) 0.5251(4) 0.05985(15) 0.0997(11) Uani 1 1 d D U . . .
N4 N 0.4722(2) 0.5279(3) 0.22949(11) 0.0416(7) Uani 1 1 d D U . . .
H4 H 0.4729 0.4427 0.2392 0.050 Uiso 1 1 calc R U . . .
C7 C 0.0399(4) 0.6216(7) 0.1237(3) 0.116(2) Uani 1 1 d D U . . .
H7A H 0.0379 0.6827 0.1611 0.140 Uiso 1 1 calc R U . . .
C5 C -0.0198(5) 0.6935(8) 0.0687(3) 0.167(3) Uani 1 1 d D U . . .
H5A H 0.0237 0.7752 0.0580 0.251 Uiso 1 1 calc R U . . .
H5B H -0.1004 0.7166 0.0814 0.251 Uiso 1 1 calc R U . . .
H5C H -0.0205 0.6346 0.0317 0.251 Uiso 1 1 calc R U . . .
C6 C -0.0207(6) 0.4910(9) 0.1430(4) 0.209(4) Uani 1 1 d D U . . .
H6A H -0.0551 0.4497 0.1058 0.314 Uiso 1 1 calc R U . . .
H6B H -0.0827 0.5097 0.1747 0.314 Uiso 1 1 calc R U . . .
H6C H 0.0368 0.4300 0.1610 0.314 Uiso 1 1 calc R U . . .
C8 C 0.1704(3) 0.5933(5) 0.1054(2) 0.0724(13) Uani 1 1 d D U . . .
C9 C 0.4123(3) 0.6315(3) 0.12686(15) 0.0410(9) Uani 1 1 d D U . . .
C10 C 0.4415(3) 0.6666(3) 0.06306(15) 0.0476(9) Uani 1 1 d D U . . .
H10 H 0.3862 0.7126 0.0383 0.057 Uiso 1 1 calc R U . . .
C11 C 0.5528(3) 0.6331(4) 0.03654(16) 0.0511(10) Uani 1 1 d D U . . .
H11 H 0.5717 0.6565 -0.0060 0.061 Uiso 1 1 calc R U . . .
C12 C 0.6351(3) 0.5658(4) 0.07268(16) 0.0508(10) Uani 1 1 d D U . . .
H12 H 0.7090 0.5418 0.0544 0.061 Uiso 1 1 calc R U . . .
C13 C 0.6076(3) 0.5336(4) 0.13683(15) 0.0466(9) Uani 1 1 d D U . . .
H13 H 0.6642 0.4901 0.1617 0.056 Uiso 1 1 calc R U . . .
C14 C 0.4967(3) 0.5658(3) 0.16411(14) 0.0384(8) Uani 1 1 d D U . . .
C15 C 0.4476(3) 0.6196(4) 0.27754(14) 0.0416(9) Uani 1 1 d D U . . .
C16 C 0.4337(3) 0.5596(3) 0.34585(14) 0.0436(9) Uani 1 1 d D U . . .
C17 C 0.3747(3) 0.6655(4) 0.39047(15) 0.0565(10) Uani 1 1 d D U . . .
H17A H 0.3786 0.6335 0.4347 0.068 Uiso 1 1 calc R U . . .
H17B H 0.4200 0.7497 0.3873 0.068 Uiso 1 1 calc R U . . .
C18 C 0.2454(4) 0.6954(5) 0.3756(2) 0.0743(12) Uani 1 1 d D U . . .
H18A H 0.2421 0.7408 0.3341 0.089 Uiso 1 1 calc R U . . .
H18B H 0.2124 0.7569 0.4081 0.089 Uiso 1 1 calc R U . . .
C19 C 0.1697(4) 0.5674(5) 0.3740(2) 0.0897(14) Uani 1 1 d D U . . .
H19A H 0.0902 0.5900 0.3596 0.108 Uiso 1 1 calc R U . . .
H19B H 0.1619 0.5296 0.4172 0.108 Uiso 1 1 calc R U . . .
C20 C 0.2260(4) 0.4613(5) 0.3286(2) 0.0802(13) Uani 1 1 d D U . . .
H20A H 0.1795 0.3779 0.3309 0.096 Uiso 1 1 calc R U . . .
H20B H 0.2246 0.4948 0.2846 0.096 Uiso 1 1 calc R U . . .
C21 C 0.3540(3) 0.4312(4) 0.34630(17) 0.0614(11) Uani 1 1 d D U . . .
H21A H 0.3876 0.3653 0.3160 0.074 Uiso 1 1 calc R U . . .
H21B H 0.3543 0.3905 0.3890 0.074 Uiso 1 1 calc R U . . .
C22 C 0.5579(3) 0.5171(4) 0.37039(16) 0.0568(10) Uani 1 1 d D U . . .
H22A H 0.5454 0.4741 0.4122 0.068 Uiso 1 1 calc R U . A 1
H22B H 0.5895 0.4477 0.3413 0.068 Uiso 1 1 calc R U . A 1
C23A C 0.6551(3) 0.6254(4) 0.37769(16) 0.0644(11) Uani 0.5 1 d D U P B 1
H23A H 0.6181 0.7062 0.3976 0.077 Uiso 0.5 1 calc R U P B 1
C24A C 0.7244(10) 0.6713(16) 0.3166(4) 0.088(5) Uani 0.5 1 d D U P B 1
H24A H 0.6678 0.7057 0.2858 0.105 Uiso 0.5 1 calc R U P B 1
H24B H 0.7767 0.7461 0.3278 0.105 Uiso 0.5 1 calc R U P B 1
C26A C 0.7362(9) 0.5591(11) 0.4277(5) 0.073(3) Uani 0.5 1 d D U P B 1
H26A H 0.6873 0.5307 0.4647 0.088 Uiso 0.5 1 calc R U P B 1
H26B H 0.7723 0.4779 0.4089 0.088 Uiso 0.5 1 calc R U P B 1
C25A C 0.7990(9) 0.5606(12) 0.2842(5) 0.115(4) Uani 0.5 1 d D U P B 1
H25A H 0.8377 0.5965 0.2460 0.172 Uiso 0.5 1 calc R U P B 1
H25B H 0.7482 0.4859 0.2728 0.172 Uiso 0.5 1 calc R U P B 1
H25C H 0.8584 0.5292 0.3134 0.172 Uiso 0.5 1 calc R U P B 1
C27A C 0.8341(7) 0.6511(10) 0.4509(4) 0.086(3) Uani 0.5 1 d D U P B 1
H27A H 0.8691 0.6122 0.4885 0.129 Uiso 0.5 1 calc R U P B 1
H27B H 0.8013 0.7390 0.4614 0.129 Uiso 0.5 1 calc R U P B 1
H27C H 0.8945 0.6609 0.4174 0.129 Uiso 0.5 1 calc R U P B 1
C23B C 0.6551(3) 0.6254(4) 0.37769(16) 0.0644(11) Uani 0.5 1 d D U P B 2
H23B H 0.6129 0.7128 0.3810 0.077 Uiso 0.5 1 calc R U P B 2
C24B C 0.7314(11) 0.6328(16) 0.3142(4) 0.080(4) Uani 0.5 1 d D U P B 2
H24C H 0.7682 0.5442 0.3075 0.095 Uiso 0.5 1 calc R U P B 2
H24D H 0.6770 0.6470 0.2791 0.095 Uiso 0.5 1 calc R U P B 2
C26B C 0.7351(10) 0.6188(12) 0.4368(4) 0.078(4) Uani 0.5 1 d D U P B 2
H26C H 0.7825 0.7015 0.4385 0.094 Uiso 0.5 1 calc R U P B 2
H26D H 0.6845 0.6157 0.4756 0.094 Uiso 0.5 1 calc R U P B 2
C25B C 0.8298(8) 0.7396(11) 0.3078(5) 0.109(3) Uani 0.5 1 d D U P B 2
H25D H 0.8598 0.7419 0.2640 0.164 Uiso 0.5 1 calc R U P B 2
H25E H 0.8936 0.7169 0.3360 0.164 Uiso 0.5 1 calc R U P B 2
H25F H 0.7979 0.8274 0.3193 0.164 Uiso 0.5 1 calc R U P B 2
C27B C 0.8179(8) 0.4977(9) 0.4366(4) 0.086(3) Uani 0.5 1 d D U P B 2
H27D H 0.8459 0.4826 0.4795 0.128 Uiso 0.5 1 calc R U P B 2
H27E H 0.8850 0.5149 0.4079 0.128 Uiso 0.5 1 calc R U P B 2
H27F H 0.7758 0.4183 0.4223 0.128 Uiso 0.5 1 calc R U P B 2
 
loop_
 _atom_site_aniso_label
 _atom_site_aniso_U_11
 _atom_site_aniso_U_22
 _atom_site_aniso_U_33
 _atom_site_aniso_U_23
 _atom_site_aniso_U_13
 _atom_site_aniso_U_12
S1 0.0563(6) 0.0518(7) 0.0476(6) -0.0066(4) 0.0028(4) 0.0006(5)
O2 0.0799(18) 0.0269(15) 0.0408(13) 0.0007(11) 0.0050(11) -0.0011(13)
O3 0.0672(19) 0.134(3) 0.097(2) -0.064(2) 0.0114(16) -0.0179(19)
N4 0.0627(18) 0.0268(17) 0.0351(15) 0.0010(12) 0.0040(13) -0.0054(14)
C7 0.053(3) 0.175(6) 0.122(4) -0.079(4) 0.005(3) -0.007(3)
C5 0.101(4) 0.216(7) 0.187(6) -0.092(5) -0.037(4) 0.043(5)
C6 0.091(5) 0.236(8) 0.299(10) -0.043(7) 0.067(6) -0.059(5)
C8 0.061(2) 0.085(3) 0.071(3) -0.026(2) 0.005(2) -0.010(2)
C9 0.053(2) 0.029(2) 0.0405(18) -0.0036(15) 0.0024(15) -0.0083(17)
C10 0.067(2) 0.037(2) 0.0383(19) 0.0028(16) -0.0027(17) -0.0095(19)
C11 0.071(2) 0.046(2) 0.0362(19) -0.0029(17) 0.0065(18) -0.016(2)
C12 0.055(2) 0.051(3) 0.046(2) -0.0097(18) 0.0105(17) -0.0118(19)
C13 0.053(2) 0.042(2) 0.045(2) -0.0081(16) 0.0007(16) -0.0020(18)
C14 0.054(2) 0.025(2) 0.0351(18) -0.0048(14) 0.0033(15) -0.0061(17)
C15 0.050(2) 0.035(2) 0.0392(18) -0.0015(17) 0.0018(15) -0.0013(18)
C16 0.063(2) 0.034(2) 0.0341(17) 0.0042(15) 0.0055(15) 0.0018(18)
C17 0.083(3) 0.046(2) 0.0403(19) 0.0037(16) 0.0123(18) 0.007(2)
C18 0.074(3) 0.076(3) 0.071(3) 0.013(2) 0.021(2) 0.014(2)
C19 0.068(3) 0.108(4) 0.092(3) 0.026(3) 0.013(2) -0.004(3)
C20 0.089(3) 0.079(3) 0.073(3) 0.021(2) 0.005(2) -0.031(3)
C21 0.087(3) 0.050(3) 0.047(2) 0.0111(18) 0.0129(19) -0.010(2)
C22 0.080(2) 0.050(2) 0.0411(19) 0.0062(17) 0.0023(17) 0.0088(19)
C23A 0.074(2) 0.054(3) 0.065(2) -0.0058(19) -0.0143(18) 0.012(2)
C24A 0.072(7) 0.108(11) 0.084(6) 0.037(5) -0.035(5) -0.048(6)
C26A 0.077(6) 0.091(9) 0.052(5) -0.006(5) -0.010(4) 0.010(5)
C25A 0.099(7) 0.154(11) 0.091(7) -0.008(6) 0.005(6) -0.019(7)
C27A 0.075(6) 0.110(8) 0.074(6) -0.016(5) -0.017(5) -0.004(5)
C23B 0.074(2) 0.054(3) 0.065(2) -0.0058(19) -0.0143(18) 0.012(2)
C24B 0.095(8) 0.068(8) 0.076(6) 0.020(5) -0.026(5) -0.022(6)
C26B 0.093(7) 0.084(9) 0.059(5) -0.017(5) -0.014(5) 0.026(6)
C25B 0.105(7) 0.106(8) 0.118(8) 0.028(6) -0.015(6) -0.019(6)
C27B 0.092(6) 0.094(7) 0.071(6) -0.003(5) -0.016(5) 0.024(6)
 
_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
S1 C9 1.771(4) . ?
S1 C8 1.773(4) . ?
O2 C15 1.229(4) . ?
O3 C8 1.201(4) . ?
N4 C15 1.364(4) . ?
N4 C14 1.424(4) . ?
C7 C6 1.499(8) . ?
C7 C5 1.510(8) . ?
C7 C8 1.523(6) . ?
C9 C14 1.392(5) . ?
C9 C10 1.396(4) . ?
C10 C11 1.386(5) . ?
C11 C12 1.370(5) . ?
C12 C13 1.392(5) . ?
C13 C14 1.385(5) . ?
C15 C16 1.536(5) . ?
C16 C17 1.529(4) . ?
C16 C21 1.543(5) . ?
C16 C22 1.548(5) . ?
C17 C18 1.514(5) . ?
C18 C19 1.516(6) . ?
C19 C20 1.528(6) . ?
C20 C21 1.515(6) . ?
C22 C23A 1.531(5) . ?
C23A C24A 1.534(4) . ?
C23A C26A 1.539(7) . ?
C24A C25A 1.515(11) . ?
C26A C27A 1.506(9) . ?
C24B C25B 1.522(11) . ?
C26B C27B 1.507(8) . ?
 
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
C9 S1 C8 103.22(19) . . ?
C15 N4 C14 123.5(3) . . ?
C6 C7 C5 113.3(5) . . ?
C6 C7 C8 109.5(5) . . ?
C5 C7 C8 109.7(5) . . ?
O3 C8 C7 123.5(4) . . ?
O3 C8 S1 124.8(3) . . ?
C7 C8 S1 111.7(3) . . ?
C14 C9 C10 119.6(3) . . ?
C14 C9 S1 120.7(2) . . ?
C10 C9 S1 119.7(3) . . ?
C11 C10 C9 120.2(3) . . ?
C12 C11 C10 120.4(3) . . ?
C11 C12 C13 119.7(3) . . ?
C14 C13 C12 120.7(3) . . ?
C13 C14 C9 119.4(3) . . ?
C13 C14 N4 118.5(3) . . ?
C9 C14 N4 122.1(3) . . ?
O2 C15 N4 120.8(3) . . ?
O2 C15 C16 123.5(3) . . ?
N4 C15 C16 115.7(3) . . ?
C17 C16 C15 109.2(3) . . ?
C17 C16 C21 108.1(3) . . ?
C15 C16 C21 111.3(3) . . ?
C17 C16 C22 111.2(3) . . ?
C15 C16 C22 109.6(3) . . ?
C21 C16 C22 107.5(3) . . ?
C18 C17 C16 114.1(3) . . ?
C17 C18 C19 112.4(4) . . ?
C18 C19 C20 110.8(4) . . ?
C21 C20 C19 111.2(4) . . ?
C20 C21 C16 112.8(3) . . ?
C23A C22 C16 119.4(3) . . ?
C22 C23A C24A 117.9(7) . . ?
C22 C23A C26A 101.8(4) . . ?
C24A C23A C26A 112.7(5) . . ?
C25A C24A C23A 114.5(9) . . ?
C27A C26A C23A 114.0(7) . . ?
 
_refine_diff_density_max    0.173
_refine_diff_density_min   -0.225
_refine_diff_density_rms    0.040