# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 'Ezetimibe'
;
_chemical_name_common            Ezetimibe
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H21 F2 N O3'
_chemical_formula_sum            'C24 H21 F2 N O3'
_chemical_formula_weight         409.42

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'
O O 0.0106 0.0060 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.9510(19)
_cell_length_b                   15.899(5)
_cell_length_c                   21.400(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2024.8(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2755
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.90

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.101
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   psi-scan

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            ?
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         1.596
_diffrn_reflns_theta_max         27.879
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.571
_diffrn_reflns_point_group_measured_fraction_full 0.582
_reflns_number_total             2755
_reflns_number_gt                1585
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     0.000
_reflns_Friedel_fraction_full    0.000

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       kappaCCD
_computing_cell_refinement       'HKL scalepack (otwinowski and Minir 1997)'
_computing_data_reduction        'Denzo and scalepak(otwinowski and Minir 1997)'
_computing_structure_solution    'SIR 92'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1233P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.020(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   -2(2)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2755
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1171
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.2013
_refine_ls_wR_factor_gt          0.1549
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_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
F1 F 0.7492(8) 0.2701(2) 0.40933(19) 0.1176(15) Uani 1 1 d . . . . .
C1 C 0.6511(12) 0.3404(3) 0.4330(3) 0.0758(16) Uani 1 1 d . . . . .
O1 O 0.2501(6) 0.6121(2) 0.45038(15) 0.0660(10) Uani 1 1 d . . . . .
H1O H 0.3432 0.6460 0.4376 0.099 Uiso 1 1 calc R U . . .
N1 N 0.1700(6) 0.73927(19) 0.71196(16) 0.0466(9) Uani 1 1 d . . . . .
F2 F 0.0643(7) 0.9561(2) 0.91008(15) 0.0955(12) Uani 1 1 d . . . . .
O2 O -0.0919(7) 0.7713(2) 0.63323(17) 0.0786(11) Uani 1 1 d . . . . .
C2 C 0.7572(11) 0.4129(4) 0.4244(3) 0.0813(17) Uani 1 1 d . . . . .
H2 H 0.8931 0.4145 0.4030 0.098 Uiso 1 1 calc R U . . .
O3 O 0.5238(6) 0.39902(18) 0.84575(15) 0.0634(9) Uani 1 1 d . . . . .
H31 H 0.4173 0.3886 0.8688 0.095 Uiso 1 1 calc R U . . .
C3 C 0.6626(10) 0.4865(4) 0.4478(3) 0.0732(15) Uani 1 1 d . . . . .
H3 H 0.7381 0.5372 0.4427 0.088 Uiso 1 1 calc R U . . .
C4 C 0.4575(8) 0.4854(3) 0.4787(2) 0.0525(11) Uani 1 1 d . . . . .
C5 C 0.3574(10) 0.4076(3) 0.4861(2) 0.0696(14) Uani 1 1 d . . . . .
H5 H 0.2208 0.4041 0.5071 0.084 Uiso 1 1 calc R U . . .
C6 C 0.4544(12) 0.3346(3) 0.4633(3) 0.0855(18) Uani 1 1 d . . . . .
H6 H 0.3846 0.2828 0.4688 0.103 Uiso 1 1 calc R U . . .
C7 C 0.3440(8) 0.5650(3) 0.5020(2) 0.0524(11) Uani 1 1 d . . . . .
H7 H 0.2180 0.5475 0.5285 0.063 Uiso 1 1 calc R U . . .
C8 C 0.4924(10) 0.6214(3) 0.5413(2) 0.0580(12) Uani 1 1 d . . . . .
H8A H 0.6128 0.6433 0.5155 0.070 Uiso 1 1 calc R U . . .
H8B H 0.5598 0.5883 0.5745 0.070 Uiso 1 1 calc R U . . .
C9 C 0.3636(10) 0.6947(3) 0.5701(2) 0.0627(14) Uani 1 1 d . . . . .
H9A H 0.2553 0.7153 0.5399 0.075 Uiso 1 1 calc R U . . .
H9B H 0.4682 0.7400 0.5789 0.075 Uiso 1 1 calc R U . . .
C10 C 0.2401(8) 0.6718(2) 0.6302(2) 0.0509(11) Uani 1 1 d . . . . .
H10 H 0.1728 0.6157 0.6272 0.061 Uiso 1 1 calc R U . . .
C11 C 0.3606(7) 0.6841(2) 0.69475(19) 0.0444(10) Uani 1 1 d . . . . .
H11 H 0.4994 0.7166 0.6900 0.053 Uiso 1 1 calc R U . . .
C13 C 0.3965(7) 0.6097(2) 0.73636(18) 0.0412(9) Uani 1 1 d . . . . .
C12 C 0.0728(8) 0.7348(3) 0.6549(2) 0.0548(11) Uani 1 1 d . . . . .
C14 C 0.2360(7) 0.5808(2) 0.7778(2) 0.0459(10) Uani 1 1 d . . . . .
H14 H 0.0994 0.6089 0.7809 0.055 Uiso 1 1 calc R U . . .
C15 C 0.2746(7) 0.5114(3) 0.8143(2) 0.0476(10) Uani 1 1 d . . . . .
H15 H 0.1648 0.4931 0.8420 0.057 Uiso 1 1 calc R U . . .
C16 C 0.4748(8) 0.4691(2) 0.8100(2) 0.0459(10) Uani 1 1 d . . . . .
C17 C 0.6384(7) 0.4966(3) 0.7695(2) 0.0492(10) Uani 1 1 d . . . . .
H17 H 0.7741 0.4679 0.7666 0.059 Uiso 1 1 calc R U . . .
C18 C 0.6015(7) 0.5667(2) 0.7332(2) 0.0471(10) Uani 1 1 d . . . . .
H18 H 0.7135 0.5856 0.7064 0.056 Uiso 1 1 calc R U . . .
C19 C 0.1385(7) 0.7916(2) 0.7647(2) 0.0457(10) Uani 1 1 d . . . . .
C20 C -0.0592(8) 0.8380(3) 0.7710(2) 0.0547(12) Uani 1 1 d . . . . .
H20 H -0.1743 0.8321 0.7419 0.066 Uiso 1 1 calc R U . . .
C21 C -0.0827(9) 0.8924(3) 0.8204(2) 0.0609(13) Uani 1 1 d . . . . .
H21 H -0.2126 0.9244 0.8249 0.073 Uiso 1 1 calc R U . . .
C22 C 0.0890(10) 0.8988(3) 0.8629(2) 0.0612(13) Uani 1 1 d . . . . .
C23 C 0.2789(9) 0.8523(3) 0.8590(2) 0.0587(12) Uani 1 1 d . . . . .
H23 H 0.3905 0.8572 0.8892 0.070 Uiso 1 1 calc R U . . .
C24 C 0.3043(8) 0.7979(3) 0.8098(2) 0.0530(11) Uani 1 1 d . . . . .
H24 H 0.4333 0.7652 0.8067 0.064 Uiso 1 1 calc R U . . .


_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 C1 1.359(6) . ?
C1 C2 1.327(8) . ?
C1 C6 1.341(9) . ?
O1 C7 1.446(5) . ?
O1 H1O 0.8200 . ?
N1 C12 1.353(6) . ?
N1 C19 1.414(5) . ?
N1 C11 1.480(5) . ?
F2 C22 1.367(5) . ?
O2 C12 1.230(6) . ?
C2 C3 1.392(8) . ?
C2 H2 0.9300 . ?
O3 C16 1.383(5) . ?
O3 H31 0.8200 . ?
C3 C4 1.388(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(7) . ?
C4 C7 1.519(6) . ?
C5 C6 1.385(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.513(7) . ?
C7 H7 0.9800 . ?
C8 C9 1.525(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.525(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C12 1.508(6) . ?
C10 C11 1.568(6) . ?
C10 H10 0.9800 . ?
C11 C13 1.497(6) . ?
C11 H11 0.9800 . ?
C13 C14 1.381(6) . ?
C13 C18 1.400(5) . ?
C14 C15 1.371(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.371(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(6) . ?
C17 C18 1.375(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C24 1.384(6) . ?
C19 C20 1.395(6) . ?
C20 C21 1.373(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.371(7) . ?
C21 H21 0.9300 . ?
C22 C23 1.353(7) . ?
C23 C24 1.371(6) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?

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
C2 C1 C6 122.8(6) . . ?
C2 C1 F1 117.3(6) . . ?
C6 C1 F1 119.9(6) . . ?
C7 O1 H1O 109.5 . . ?
C12 N1 C19 133.9(4) . . ?
C12 N1 C11 94.1(3) . . ?
C19 N1 C11 130.4(3) . . ?
C1 C2 C3 119.2(5) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C16 O3 H31 109.5 . . ?
C4 C3 C2 121.2(5) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C5 C4 C3 116.4(5) . . ?
C5 C4 C7 121.1(4) . . ?
C3 C4 C7 122.5(4) . . ?
C4 C5 C6 122.0(5) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C1 C6 C5 118.5(6) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
O1 C7 C8 110.1(3) . . ?
O1 C7 C4 110.6(3) . . ?
C8 C7 C4 114.6(4) . . ?
O1 C7 H7 107.0 . . ?
C8 C7 H7 107.0 . . ?
C4 C7 H7 107.0 . . ?
C7 C8 C9 112.6(5) . . ?
C7 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 C10 113.6(4) . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C12 C10 C9 117.1(4) . . ?
C12 C10 C11 84.9(3) . . ?
C9 C10 C11 119.5(4) . . ?
C12 C10 H10 111.0 . . ?
C9 C10 H10 111.0 . . ?
C11 C10 H10 111.0 . . ?
N1 C11 C13 115.5(3) . . ?
N1 C11 C10 86.7(3) . . ?
C13 C11 C10 119.4(3) . . ?
N1 C11 H11 111.0 . . ?
C13 C11 H11 111.0 . . ?
C10 C11 H11 111.0 . . ?
C14 C13 C18 118.1(4) . . ?
C14 C13 C11 123.1(4) . . ?
C18 C13 C11 118.8(4) . . ?
O2 C12 N1 131.0(5) . . ?
O2 C12 C10 135.0(5) . . ?
N1 C12 C10 93.9(4) . . ?
C15 C14 C13 121.1(4) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 120.2(4) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C17 120.1(4) . . ?
C15 C16 O3 122.8(4) . . ?
C17 C16 O3 117.1(4) . . ?
C18 C17 C16 120.0(4) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C13 120.5(4) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
C24 C19 C20 119.7(4) . . ?
C24 C19 N1 120.3(4) . . ?
C20 C19 N1 120.0(4) . . ?
C21 C20 C19 119.6(5) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C22 C21 C20 118.8(5) . . ?
C22 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
C23 C22 F2 119.9(5) . . ?
C23 C22 C21 122.7(4) . . ?
F2 C22 C21 117.3(5) . . ?
C22 C23 C24 119.0(5) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
C23 C24 C19 120.2(4) . . ?
C23 C24 H24 119.9 . . ?
C19 C24 H24 119.9 . . ?

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.089

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 947148'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            Ezetimibe-Imidazole
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H21 F2 N O3,C3 H4 N2'
_chemical_formula_sum            'C27 H25 F2 N3 O3'
_chemical_formula_weight         477.50

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'
O O 0.0106 0.0060 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.8320(2)
_cell_length_b                   15.7520(5)
_cell_length_c                   25.6730(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2358.47(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2150
_cell_measurement_theta_min      1.0
_cell_measurement_theta_max      28.3

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   psi-scan

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            ?
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         1.517
_diffrn_reflns_theta_max         28.260
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.554
_diffrn_reflns_point_group_measured_fraction_full 0.581
_reflns_number_total             3237
_reflns_number_gt                2150
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     0.000
_reflns_Friedel_fraction_full    0.000

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       kappaCCD
_computing_cell_refinement       'HKL scalepack (otwinowski and Minir 1997)'
_computing_data_reduction        'Denzo and scalepak(otwinowski and Minir 1997)'
_computing_structure_solution    'SIR 92'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1338P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.031(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   -0.7(19)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3237
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0600
_refine_ls_wR_factor_ref         0.1994
_refine_ls_wR_factor_gt          0.1678
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.003
_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
C1 C 0.9124(9) 0.4463(3) 0.82780(15) 0.0648(13) Uani 1 1 d . . . . .
F1 F 1.0367(7) 0.4626(2) 0.87149(10) 0.1005(12) Uani 1 1 d . . . . .
O1 O 0.4012(5) 0.32199(18) 0.69304(10) 0.0506(7) Uani 1 1 d . . . . .
C18 C 0.9577(7) 0.3991(2) 0.44990(13) 0.0448(9) Uani 1 1 d . . . . .
H18 H 1.0981 0.4269 0.4480 0.054 Uiso 1 1 calc R U . . .
C2 C 1.0038(9) 0.3909(3) 0.79217(16) 0.0607(11) Uani 1 1 d . . . . .
H2 H 1.1439 0.3644 0.7980 0.073 Uiso 1 1 calc R U . . .
O3 O 0.6453(6) 0.22597(18) 0.38645(11) 0.0615(8) Uani 1 1 d . . . . .
H31A H 0.7501 0.2167 0.3659 0.11(2) Uiso 1 1 calc R . . . .
N3 N 1.0422(5) 0.55062(19) 0.51867(10) 0.0436(7) Uani 1 1 d . . . . .
C3 C 0.8780(7) 0.3761(2) 0.74681(14) 0.0489(9) Uani 1 1 d . . . . .
H3 H 0.9352 0.3384 0.7221 0.059 Uiso 1 1 calc R U . . .
C4 C 0.6716(6) 0.4156(2) 0.73771(13) 0.0417(8) Uani 1 1 d . . . . .
N4 N 0.0767(9) 0.6138(3) 0.7344(2) 0.1062(18) Uani 1 1 d . . . . .
H4 H -0.0494 0.5870 0.7290 0.127 Uiso 1 1 calc R U . . .
C5 C 0.5862(7) 0.4709(2) 0.77511(14) 0.0512(10) Uani 1 1 d . . . . .
H5 H 0.4463 0.4978 0.7697 0.061 Uiso 1 1 calc R U . . .
H5O H 0.469(14) 0.274(4) 0.707(2) 0.12(2) Uiso 1 1 d . . . . .
C6 C 0.7088(9) 0.4862(3) 0.82067(15) 0.0673(13) Uani 1 1 d . . . . .
H6 H 0.6520 0.5231 0.8458 0.081 Uiso 1 1 calc R U . . .
C7 C 0.5311(7) 0.3993(2) 0.68879(13) 0.0431(8) Uani 1 1 d . . . . .
H7 H 0.4367 0.4511 0.6881 0.052 Uiso 1 1 d R U . . .
O2 O 1.2865(5) 0.5702(2) 0.59077(10) 0.0671(9) Uani 1 1 d . . . . .
C8 C 0.6718(7) 0.3961(2) 0.63866(13) 0.0479(9) Uani 1 1 d . . . . .
H8A H 0.5676 0.3938 0.6097 0.058 Uiso 1 1 d R U . . .
H8B H 0.7675 0.3466 0.6385 0.058 Uiso 1 1 d R U . . .
C11 C 0.8436(6) 0.4930(2) 0.52656(13) 0.0432(8) Uani 1 1 d . . . . .
H11 H 0.7057 0.5263 0.5270 0.052 Uiso 1 1 d R U . . .
C12 C 1.1306(7) 0.5357(2) 0.56715(13) 0.0460(9) Uani 1 1 d . . . . .
C13 C 0.8000(7) 0.4244(2) 0.48651(13) 0.0424(8) Uani 1 1 d . . . . .
C10 C 0.9584(7) 0.4670(2) 0.57902(12) 0.0460(9) Uani 1 1 d . . . . .
H10 H 1.0133 0.4096 0.5771 0.055 Uiso 1 1 d R U . . .
C14 C 0.5919(7) 0.3812(3) 0.48880(15) 0.0528(10) Uani 1 1 d . . . . .
H14 H 0.4826 0.3977 0.5132 0.063 Uiso 1 1 calc R U . . .
C16 C 0.7049(7) 0.2912(2) 0.41864(14) 0.0457(9) Uani 1 1 d . . . . .
C17 C 0.9133(7) 0.3335(2) 0.41588(14) 0.0459(9) Uani 1 1 d . . . . .
H17 H 1.0222 0.3176 0.3913 0.055 Uiso 1 1 calc R U . . .
N5 N 0.3535(7) 0.6862(2) 0.77292(14) 0.0623(10) Uani 1 1 d . . . . .
C19 C 1.0930(7) 0.6122(2) 0.48037(13) 0.0432(8) Uani 1 1 d . . . . .
F2 F 1.2378(6) 0.79465(19) 0.37178(11) 0.0929(11) Uani 1 1 d . . . . .
C20 C 0.9409(7) 0.6273(3) 0.44002(15) 0.0517(10) Uani 1 1 d . . . . .
H20 H 0.8061 0.5959 0.4377 0.065(13) Uiso 1 1 calc R . . . .
C23 C 1.3429(8) 0.7192(2) 0.44625(15) 0.0563(11) Uani 1 1 d . . . . .
H23 H 1.4788 0.7501 0.4476 0.068 Uiso 1 1 calc R U . . .
C21 C 0.9885(9) 0.6887(3) 0.40307(17) 0.0632(12) Uani 1 1 d . . . . .
H21 H 0.8874 0.6991 0.3758 0.076 Uiso 1 1 calc R U . . .
C9 C 0.8253(8) 0.4732(3) 0.63016(13) 0.0507(10) Uani 1 1 d . . . . .
H9A H 0.9321 0.4767 0.6585 0.061 Uiso 1 1 d R U . . .
H9B H 0.7329 0.5236 0.6293 0.061 Uiso 1 1 d R U . . .
C15 C 0.5446(7) 0.3150(3) 0.45595(15) 0.0558(11) Uani 1 1 d . . . . .
H15 H 0.4060 0.2860 0.4586 0.067 Uiso 1 1 calc R U . . .
C26 C 0.2414(8) 0.6272(3) 0.69999(14) 0.0506(10) Uani 1 1 d . . . . .
H26A H 0.2427 0.6095 0.6654 0.067(13) Uiso 1 1 calc R . . . .
C25 C 0.1432(9) 0.6504(3) 0.78016(18) 0.0669(13) Uani 1 1 d . . . . .
H25 H 0.0594 0.6509 0.8110 0.098(18) Uiso 1 1 calc R . . . .
C27 C 0.4030(10) 0.6704(3) 0.72390(17) 0.0641(12) Uani 1 1 d . . . . .
H27 H 0.5380 0.6878 0.7079 0.042(11) Uiso 1 1 calc R . . . .
C24 C 1.2954(7) 0.6582(2) 0.48329(14) 0.0494(9) Uani 1 1 d . . . . .
H24 H 1.3988 0.6479 0.5101 0.059 Uiso 1 1 calc R U . . .
C22 C 1.1864(9) 0.7335(3) 0.40754(15) 0.0614(12) 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
C1 C6 1.356(7) . ?
C1 F1 1.360(5) . ?
C1 C2 1.371(7) . ?
O1 C7 1.438(4) . ?
O1 H5O 0.92(7) . ?
C18 C13 1.374(5) . ?
C18 C17 1.378(5) . ?
C18 H18 0.9300 . ?
C2 C3 1.396(6) . ?
C2 H2 0.9300 . ?
O3 C16 1.364(4) . ?
O3 H31A 0.8200 . ?
N3 C12 1.367(4) . ?
N3 C19 1.413(4) . ?
N3 C11 1.485(5) . ?
C3 C4 1.375(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(5) . ?
C4 C7 1.522(5) . ?
N4 C26 1.322(7) . ?
N4 C25 1.365(6) . ?
N4 H4 0.8600 . ?
C5 C6 1.392(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.527(5) . ?
C7 H7 0.9842 . ?
O2 C12 1.221(5) . ?
C8 C9 1.524(6) . ?
C8 H8A 0.9601 . ?
C8 H8B 0.9600 . ?
C11 C13 1.513(5) . ?
C11 C10 1.559(5) . ?
C11 H11 0.9600 . ?
C12 C10 1.507(6) . ?
C13 C14 1.393(6) . ?
C10 C9 1.529(5) . ?
C10 H10 0.9607 . ?
C14 C15 1.370(5) . ?
C14 H14 0.9300 . ?
C16 C17 1.387(6) . ?
C16 C15 1.390(5) . ?
C17 H17 0.9300 . ?
N5 C27 1.315(6) . ?
N5 C25 1.362(7) . ?
C19 C20 1.384(5) . ?
C19 C24 1.387(5) . ?
F2 C22 1.364(5) . ?
C20 C21 1.384(6) . ?
C20 H20 0.9300 . ?
C23 C22 1.368(6) . ?
C23 C24 1.381(5) . ?
C23 H23 0.9300 . ?
C21 C22 1.357(7) . ?
C21 H21 0.9300 . ?
C9 H9A 0.9602 . ?
C9 H9B 0.9601 . ?
C15 H15 0.9300 . ?
C26 C27 1.314(7) . ?
C26 H26A 0.9300 . ?
C25 H25 0.9300 . ?
C27 H27 0.9300 . ?
C24 H24 0.9300 . ?

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
C6 C1 F1 119.4(5) . . ?
C6 C1 C2 123.0(4) . . ?
F1 C1 C2 117.6(5) . . ?
C7 O1 H5O 120(5) . . ?
C13 C18 C17 121.7(4) . . ?
C13 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C1 C2 C3 117.3(5) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C16 O3 H31A 109.5 . . ?
C12 N3 C19 132.3(3) . . ?
C12 N3 C11 93.7(3) . . ?
C19 N3 C11 132.7(3) . . ?
C4 C3 C2 121.7(4) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 118.7(4) . . ?
C3 C4 C7 122.4(3) . . ?
C5 C4 C7 118.9(3) . . ?
C26 N4 C25 107.5(5) . . ?
C26 N4 H4 126.2 . . ?
C25 N4 H4 126.2 . . ?
C4 C5 C6 120.3(4) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.9(4) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
O1 C7 C4 111.4(3) . . ?
O1 C7 C8 108.6(3) . . ?
C4 C7 C8 114.3(3) . . ?
O1 C7 H7 114.1 . . ?
C4 C7 H7 100.1 . . ?
C8 C7 H7 108.2 . . ?
C9 C8 C7 114.2(3) . . ?
C9 C8 H8A 107.0 . . ?
C7 C8 H8A 108.3 . . ?
C9 C8 H8B 107.8 . . ?
C7 C8 H8B 110.0 . . ?
H8A C8 H8B 109.5 . . ?
N3 C11 C13 118.3(3) . . ?
N3 C11 C10 86.7(3) . . ?
C13 C11 C10 118.1(3) . . ?
N3 C11 H11 108.7 . . ?
C13 C11 H11 104.9 . . ?
C10 C11 H11 119.6 . . ?
O2 C12 N3 131.0(4) . . ?
O2 C12 C10 135.7(3) . . ?
N3 C12 C10 93.2(3) . . ?
C18 C13 C14 118.0(3) . . ?
C18 C13 C11 124.1(3) . . ?
C14 C13 C11 117.8(3) . . ?
C12 C10 C9 117.8(3) . . ?
C12 C10 C11 85.6(3) . . ?
C9 C10 C11 120.5(3) . . ?
C12 C10 H10 116.3 . . ?
C9 C10 H10 105.9 . . ?
C11 C10 H10 110.2 . . ?
C15 C14 C13 121.5(4) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
O3 C16 C17 123.6(4) . . ?
O3 C16 C15 116.6(3) . . ?
C17 C16 C15 119.7(3) . . ?
C18 C17 C16 119.5(3) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C27 N5 C25 104.5(4) . . ?
C20 C19 C24 119.8(3) . . ?
C20 C19 N3 120.3(3) . . ?
C24 C19 N3 120.0(3) . . ?
C21 C20 C19 120.3(4) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C22 C23 C24 118.7(4) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C22 C21 C20 118.4(4) . . ?
C22 C21 H21 120.8 . . ?
C20 C21 H21 120.8 . . ?
C8 C9 C10 111.8(3) . . ?
C8 C9 H9A 108.6 . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 109.5 . . ?
C14 C15 C16 119.6(4) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C27 C26 N4 106.9(4) . . ?
C27 C26 H26A 126.5 . . ?
N4 C26 H26A 126.5 . . ?
N5 C25 N4 108.2(4) . . ?
N5 C25 H25 125.9 . . ?
N4 C25 H25 125.9 . . ?
C26 C27 N5 112.8(5) . . ?
C26 C27 H27 123.6 . . ?
N5 C27 H27 123.6 . . ?
C23 C24 C19 119.8(4) . . ?
C23 C24 H24 120.1 . . ?
C19 C24 H24 120.1 . . ?
C21 C22 F2 119.8(4) . . ?
C21 C22 C23 122.9(4) . . ?
F2 C22 C23 117.3(4) . . ?

_refine_diff_density_max         0.450
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.076

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 947149'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 'Ezetimibe-Formamide'
;
_chemical_name_common            Ezetimibe-Formamide
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H21 F2 N1 O3, C1 H3 N1 O1'
_chemical_formula_sum            'C25 H24 F2 N2 O4'
_chemical_formula_weight         454.46

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'
O O 0.0106 0.0060 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.1400(2)
_cell_length_b                   17.0770(7)
_cell_length_c                   21.3500(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2238.61(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   psi-scan

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            ?
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         3.055
_diffrn_reflns_theta_max         27.118
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.557
_diffrn_reflns_point_group_measured_fraction_full 0.564
_reflns_number_total             2749
_reflns_number_gt                1791
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     0.000
_reflns_Friedel_fraction_full    0.000

_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       KappaCCD
_computing_cell_refinement       'HKL scalepack (otwinowski and Minir 1997)'
_computing_data_reduction        'Denzo and scalepak(otwinowski and Minir 1997)'
_computing_structure_solution    'SIR 92'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0680P)²+0.4141P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   1(2)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2749
_refine_ls_number_parameters     324
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0551
_refine_ls_wR_factor_ref         0.1599
_refine_ls_wR_factor_gt          0.1341
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_restrained_S_all      1.148
_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
O1 O 0.5292(6) 0.57633(18) 0.50423(18) 0.0579(9) Uani 1 1 d . . . . .
H111 H 0.4971 0.5830 0.4673 0.09(2) Uiso 1 1 calc R . . . .
F2 F -0.0955(5) 0.3093(2) 0.57900(18) 0.0840(11) Uani 1 1 d . . . . .
O4 O 1.3925(5) 0.5952(2) 0.38225(18) 0.0630(10) Uani 1 1 d . . . . .
O5 O 0.7634(8) 0.3212(2) 0.12402(18) 0.0730(11) Uani 1 1 d . . . . .
H51 H 0.8721 0.2949 0.1166 0.16(4) Uiso 1 1 calc R . . . .
C6 C 1.2213(7) 0.5718(3) 0.3602(2) 0.0457(11) Uani 1 1 d . . . . .
C7 C 0.4352(8) 0.4437(3) 0.5305(2) 0.0448(10) Uani 1 1 d . . . . .
F9 F 1.2507(7) 0.8214(2) 0.13016(17) 0.0925(12) Uani 1 1 d . . . . .
C10 C 0.9900(8) 0.6674(3) 0.2179(2) 0.0527(12) Uani 1 1 d . . . . .
H10 H 0.8596 0.6398 0.2187 0.069(17) Uiso 1 1 calc R . . . .
C11 C 0.6187(8) 0.4992(2) 0.5123(2) 0.0435(10) Uani 1 1 d . . . . .
H11 H 0.7193 0.5017 0.5479 0.044(12) Uiso 1 1 calc R . . . .
C12 C 1.0470(7) 0.5134(3) 0.3794(2) 0.0455(11) Uani 1 1 d . . . . .
H12 H 1.0989 0.4592 0.3768 0.050(13) Uiso 1 1 calc R . . . .
C13 C 1.1517(7) 0.6509(2) 0.2614(2) 0.0437(10) Uani 1 1 d . . . . .
C14 C 1.0470(7) 0.4304(3) 0.2474(2) 0.0513(12) Uani 1 1 d . . . . .
H14 H 1.1833 0.4328 0.2662 0.056(14) Uiso 1 1 calc R . . . .
C15 C 0.9261(7) 0.5397(3) 0.3180(2) 0.0433(10) Uani 1 1 d . . . . .
H15 H 0.7942 0.5697 0.3276 0.045(12) Uiso 1 1 calc R . . . .
C16 C 0.8087(8) 0.3735(3) 0.1714(2) 0.0527(12) Uani 1 1 d . . . . .
C17 C 0.6460(8) 0.4228(3) 0.1906(2) 0.0575(13) Uani 1 1 d . . . . .
H17 H 0.5101 0.4207 0.1714 0.045(12) Uiso 1 1 calc R . . . .
C18 C 1.0123(9) 0.3762(3) 0.2002(2) 0.0554(13) Uani 1 1 d . . . . .
H18 H 1.1227 0.3422 0.1879 0.081(19) Uiso 1 1 calc R . . . .
C19 C 0.0820(8) 0.3528(3) 0.5631(2) 0.0564(13) Uani 1 1 d . . . . .
C20 C 0.9380(8) 0.5305(3) 0.4416(2) 0.0474(11) Uani 1 1 d . . . . .
H20A H 0.8840 0.5839 0.4413 0.049(13) Uiso 1 1 calc R . . . .
H20B H 1.0453 0.5264 0.4748 0.074(17) Uiso 1 1 calc R . . . .
C21 C 1.3470(8) 0.6909(3) 0.2600(2) 0.0488(11) Uani 1 1 d . . . . .
H21 H 1.4560 0.6791 0.2887 0.049(14) Uiso 1 1 calc R . . . .
C22 C 0.6834(8) 0.4760(3) 0.2389(2) 0.0524(12) Uani 1 1 d . . . . .
H22 H 0.5710 0.5086 0.2521 0.049(13) Uiso 1 1 calc R . . . .
C23 C 1.0237(10) 0.7254(3) 0.1732(3) 0.0646(14) Uani 1 1 d . . . . .
H23 H 0.9164 0.7370 0.1439 0.072(17) Uiso 1 1 calc R . . . .
C24 C 0.3128(9) 0.4600(3) 0.5838(2) 0.0579(13) Uani 1 1 d . . . . .
H24 H 0.3518 0.5020 0.6092 0.058(15) Uiso 1 1 calc R . . . .
C25 C 0.7501(8) 0.4752(3) 0.4558(2) 0.0455(11) Uani 1 1 d . . . . .
H25A H 0.6546 0.4730 0.4196 0.056(14) Uiso 1 1 calc R . . . .
H25B H 0.8076 0.4230 0.4626 0.045(12) Uiso 1 1 calc R . . . .
C26 C 0.3737(8) 0.3793(3) 0.4946(2) 0.0528(12) Uani 1 1 d . . . . .
H26 H 0.4526 0.3669 0.4588 0.071(17) Uiso 1 1 calc R . . . .
C27 C 0.1968(9) 0.3333(3) 0.5113(3) 0.0612(14) Uani 1 1 d . . . . .
H27 H 0.1579 0.2899 0.4874 0.064(16) Uiso 1 1 calc R . . . .
C28 C 1.3798(10) 0.7491(3) 0.2152(3) 0.0603(13) Uani 1 1 d . . . . .
H28 H 1.5100 0.7768 0.2138 0.071(17) Uiso 1 1 calc R . . . .
C29 C 1.2155(11) 0.7647(3) 0.1731(2) 0.0623(14) Uani 1 1 d . . . . .
C31 C 0.1345(9) 0.4149(3) 0.5997(3) 0.0633(14) Uani 1 1 d . . . . .
H31 H 0.0517 0.4270 0.6349 0.074(17) Uiso 1 1 calc R . . . .
O32 O 0.3907(10) 0.7701(3) 0.5967(3) 0.125(2) Uani 1 1 d . . . . .
C33 C 0.2211(14) 0.7490(4) 0.5758(4) 0.0846(19) Uani 1 1 d . . . . .
H33 H 0.1018 0.7822 0.5798 0.24(6) Uiso 1 1 calc R . . . .
N34 N 0.1937(13) 0.6853(4) 0.5491(4) 0.128(3) Uani 1 1 d . . . . .
H34A H 0.3011 0.6535 0.5447 0.09(2) Uiso 1 1 calc R . . . .
H34B H 0.0672 0.6730 0.5349 0.17(5) Uiso 1 1 calc R . . . .
C35 C 0.8854(7) 0.4811(3) 0.2675(2) 0.0426(10) Uani 1 1 d . . . . .
N36 N 1.1163(6) 0.5925(2) 0.30686(17) 0.0449(9) 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 C11 1.437(5) . ?
O1 H111 0.8200 . ?
F2 C19 1.362(6) . ?
O4 C6 1.219(6) . ?
O5 C16 1.378(6) . ?
O5 H51 0.8200 . ?
C6 N36 1.355(6) . ?
C6 C12 1.519(6) . ?
C7 C24 1.391(7) . ?
C7 C26 1.393(7) . ?
C7 C11 1.524(7) . ?
F9 C29 1.351(6) . ?
C10 C13 1.388(7) . ?
C10 C23 1.390(7) . ?
C10 H10 0.9300 . ?
C11 C25 1.508(6) . ?
C11 H11 0.9800 . ?
C12 C20 1.516(6) . ?
C12 C15 1.572(6) . ?
C12 H12 0.9800 . ?
C13 C21 1.381(6) . ?
C13 N36 1.408(6) . ?
C14 C18 1.385(7) . ?
C14 C35 1.386(6) . ?
C14 H14 0.9300 . ?
C15 C35 1.491(6) . ?
C15 N36 1.494(5) . ?
C15 H15 0.9800 . ?
C16 C17 1.369(7) . ?
C16 C18 1.393(7) . ?
C17 C22 1.393(7) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C27 1.353(7) . ?
C19 C31 1.356(8) . ?
C20 C25 1.521(7) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C28 1.393(7) . ?
C21 H21 0.9300 . ?
C22 C35 1.386(6) . ?
C22 H22 0.9300 . ?
C23 C29 1.356(8) . ?
C23 H23 0.9300 . ?
C24 C31 1.380(7) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.387(7) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C29 1.378(8) . ?
C28 H28 0.9300 . ?
C31 H31 0.9300 . ?
O32 C33 1.189(9) . ?
C33 N34 1.240(9) . ?
C33 H33 0.9300 . ?
N34 H34A 0.8600 . ?
N34 H34B 0.8600 . ?

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
C11 O1 H111 109.5 . . ?
C16 O5 H51 109.5 . . ?
O4 C6 N36 130.5(5) . . ?
O4 C6 C12 135.9(4) . . ?
N36 C6 C12 93.6(4) . . ?
C24 C7 C26 117.5(5) . . ?
C24 C7 C11 119.0(4) . . ?
C26 C7 C11 123.5(4) . . ?
C13 C10 C23 119.9(5) . . ?
C13 C10 H10 120.1 . . ?
C23 C10 H10 120.1 . . ?
O1 C11 C25 111.0(4) . . ?
O1 C11 C7 108.6(4) . . ?
C25 C11 C7 115.5(4) . . ?
O1 C11 H11 107.1 . . ?
C25 C11 H11 107.1 . . ?
C7 C11 H11 107.1 . . ?
C20 C12 C6 114.9(4) . . ?
C20 C12 C15 117.9(4) . . ?
C6 C12 C15 85.4(3) . . ?
C20 C12 H12 112.0 . . ?
C6 C12 H12 112.0 . . ?
C15 C12 H12 112.0 . . ?
C21 C13 C10 120.3(4) . . ?
C21 C13 N36 120.0(4) . . ?
C10 C13 N36 119.7(4) . . ?
C18 C14 C35 122.2(4) . . ?
C18 C14 H14 118.9 . . ?
C35 C14 H14 118.9 . . ?
C35 C15 N36 114.9(4) . . ?
C35 C15 C12 119.4(4) . . ?
N36 C15 C12 86.3(3) . . ?
C35 C15 H15 111.3 . . ?
N36 C15 H15 111.3 . . ?
C12 C15 H15 111.3 . . ?
C17 C16 O5 118.1(5) . . ?
C17 C16 C18 120.2(5) . . ?
O5 C16 C18 121.7(5) . . ?
C16 C17 C22 120.2(5) . . ?
C16 C17 H17 119.9 . . ?
C22 C17 H17 119.9 . . ?
C14 C18 C16 118.7(5) . . ?
C14 C18 H18 120.6 . . ?
C16 C18 H18 120.6 . . ?
C27 C19 C31 122.7(5) . . ?
C27 C19 F2 119.1(5) . . ?
C31 C19 F2 118.2(5) . . ?
C12 C20 C25 113.0(4) . . ?
C12 C20 H20A 109.0 . . ?
C25 C20 H20A 109.0 . . ?
C12 C20 H20B 109.0 . . ?
C25 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C13 C21 C28 119.6(5) . . ?
C13 C21 H21 120.2 . . ?
C28 C21 H21 120.2 . . ?
C35 C22 C17 121.0(5) . . ?
C35 C22 H22 119.5 . . ?
C17 C22 H22 119.5 . . ?
C29 C23 C10 118.9(5) . . ?
C29 C23 H23 120.6 . . ?
C10 C23 H23 120.6 . . ?
C31 C24 C7 121.2(5) . . ?
C31 C24 H24 119.4 . . ?
C7 C24 H24 119.4 . . ?
C11 C25 C20 113.4(4) . . ?
C11 C25 H25A 108.9 . . ?
C20 C25 H25A 108.9 . . ?
C11 C25 H25B 108.9 . . ?
C20 C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?
C27 C26 C7 121.2(5) . . ?
C27 C26 H26 119.4 . . ?
C7 C26 H26 119.4 . . ?
C19 C27 C26 118.6(5) . . ?
C19 C27 H27 120.7 . . ?
C26 C27 H27 120.7 . . ?
C29 C28 C21 118.7(5) . . ?
C29 C28 H28 120.6 . . ?
C21 C28 H28 120.6 . . ?
F9 C29 C23 119.7(6) . . ?
F9 C29 C28 117.7(5) . . ?
C23 C29 C28 122.6(5) . . ?
C19 C31 C24 118.9(5) . . ?
C19 C31 H31 120.6 . . ?
C24 C31 H31 120.6 . . ?
O32 C33 N34 123.9(8) . . ?
O32 C33 H33 118.0 . . ?
N34 C33 H33 118.0 . . ?
C33 N34 H34A 120.0 . . ?
C33 N34 H34B 120.0 . . ?
H34A N34 H34B 120.0 . . ?
C22 C35 C14 117.7(4) . . ?
C22 C35 C15 120.7(4) . . ?
C14 C35 C15 121.6(4) . . ?
C6 N36 C13 133.6(4) . . ?
C6 N36 C15 94.6(3) . . ?
C13 N36 C15 131.1(4) . . ?

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.044

_shelxl_version_number           2013-3

_database_code_depnum_ccdc_archive 'CCDC 947150'
