# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ordered_nhc
_database_code_depnum_ccdc_archive 'CCDC 2014123'
loop_
_audit_author_name
_audit_author_address
'Birger Dittrich'
;Novartis Pharma, Basel, Switzerland
Germany
;
_audit_update_record             
;
2020-07-05 deposited with the CCDC.	2020-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-one
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H36 N2 O'
_chemical_formula_weight         404.58

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   19.2069(10)
_cell_length_b                   6.5424(3)
_cell_length_c                   20.5081(12)
_cell_angle_alpha                90
_cell_angle_beta                 109.174(3)
_cell_angle_gamma                90
_cell_volume                     2434.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9867
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      26.37

_exptl_crystal_description       cube
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.104
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6832
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker D8 diffractometer with APEX II Area Detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45356
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.103
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_full        25.025
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4276
_reflns_number_gt                3628
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0340P)²+2.1341P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4276
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1196
_refine_ls_wR_factor_gt          0.1148
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_restrained_S_all      1.154
_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 0.55506(7) 0.23239(18) 0.26955(7) 0.0192(5) Uani 1 1 d . . . . .
N1 N 0.55967(8) 0.5916(2) 0.27494(8) 0.0128(6) Uani 1 1 d . . . . .
N2 N 0.45822(8) 0.4421(2) 0.27553(8) 0.0129(6) Uani 1 1 d . . . . .
C1 C 0.52817(9) 0.4013(3) 0.27296(9) 0.0130(5) Uani 1 1 d . . . . .
C2 C 0.44806(10) 0.6538(3) 0.27771(10) 0.0181(5) Uani 1 1 d . . . . .
H2 H 0.404701 0.720545 0.279243 0.022 Uiso 1 1 calc R U . . .
C3 C 0.51026(10) 0.7453(3) 0.27725(10) 0.0177(5) Uani 1 1 d . . . . .
H3 H 0.519084 0.888377 0.278303 0.021 Uiso 1 1 calc R U . . .
C4 C 0.40349(9) 0.2891(3) 0.27186(9) 0.0133(5) Uani 1 1 d . . . . .
C5 C 0.36504(9) 0.2014(3) 0.20786(10) 0.0165(5) Uani 1 1 d . . . . .
C6 C 0.30910(10) 0.0625(3) 0.20586(11) 0.0217(5) Uani 1 1 d . . . . .
H6 H 0.281854 0.000406 0.163235 0.026 Uiso 1 1 calc R U . . .
C7 C 0.29275(11) 0.0139(3) 0.26470(11) 0.0234(5) Uani 1 1 d . . . . .
H7 H 0.253332 -0.077040 0.261951 0.028 Uiso 1 1 calc R U . . .
C8 C 0.33336(10) 0.0969(3) 0.32742(11) 0.0231(5) Uani 1 1 d . . . . .
H8 H 0.322364 0.059060 0.367692 0.028 Uiso 1 1 calc R U . . .
C9 C 0.39027(10) 0.2352(3) 0.33301(10) 0.0182(5) Uani 1 1 d . . . . .
C10 C 0.38193(10) 0.2567(3) 0.14308(10) 0.0217(6) Uani 1 1 d . . . . .
H10 H 0.431753 0.322072 0.157641 0.026 Uiso 1 1 calc R U . . .
C11 C 0.38514(14) 0.0693(4) 0.10021(12) 0.0377(7) Uani 1 1 d . . . . .
H11A H 0.335772 0.009780 0.081147 0.056 Uiso 1 1 calc R U . . .
H11B H 0.418801 -0.031702 0.129484 0.056 Uiso 1 1 calc R U . . .
H11C H 0.402926 0.109273 0.062395 0.056 Uiso 1 1 calc R U . . .
C12 C 0.32686(15) 0.4128(4) 0.10020(13) 0.0428(7) Uani 1 1 d . . . . .
H12A H 0.340117 0.450224 0.059521 0.064 Uiso 1 1 calc R U . . .
H12B H 0.327798 0.535010 0.128113 0.064 Uiso 1 1 calc R U . . .
H12C H 0.277250 0.353517 0.085404 0.064 Uiso 1 1 calc R U . . .
C13 C 0.43963(11) 0.3130(3) 0.40212(10) 0.0242(6) Uani 1 1 d . . . . .
H13A H 0.455694 0.454542 0.395367 0.029 Uiso 1 1 calc R U . . .
C14 C 0.40253(14) 0.3218(4) 0.45717(12) 0.0401(7) Uani 1 1 d . . . . .
H14A H 0.357694 0.404819 0.440462 0.060 Uiso 1 1 calc R U . . .
H14B H 0.436346 0.383035 0.499302 0.060 Uiso 1 1 calc R U . . .
H14C H 0.389646 0.183081 0.467221 0.060 Uiso 1 1 calc R U . . .
C15 C 0.50895(12) 0.1766(4) 0.42698(11) 0.0330(7) Uani 1 1 d . . . . .
H15A H 0.494344 0.035596 0.432100 0.050 Uiso 1 1 calc R U . . .
H15B H 0.541634 0.226760 0.471553 0.050 Uiso 1 1 calc R U . . .
H15C H 0.534882 0.180934 0.393057 0.050 Uiso 1 1 calc R U . . .
C16 C 0.63076(9) 0.6194(3) 0.26677(9) 0.0118(5) Uani 1 1 d . . . . .
C17 C 0.63432(10) 0.6319(3) 0.19984(9) 0.0142(5) Uani 1 1 d . . . . .
C18 C 0.70435(10) 0.6439(3) 0.19351(10) 0.0167(5) Uani 1 1 d . . . . .
H18 H 0.708773 0.650596 0.148764 0.020 Uiso 1 1 calc R U . . .
C19 C 0.76734(10) 0.6463(3) 0.25061(10) 0.0176(5) Uani 1 1 d . . . . .
H19 H 0.814456 0.651838 0.244952 0.021 Uiso 1 1 calc R U . . .
C20 C 0.76167(10) 0.6407(3) 0.31608(10) 0.0164(5) Uani 1 1 d . . . . .
H20 H 0.805192 0.646384 0.355167 0.020 Uiso 1 1 calc R U . . .
C21 C 0.69333(10) 0.6270(3) 0.32586(10) 0.0144(5) Uani 1 1 d . . . . .
C22 C 0.56531(10) 0.6285(3) 0.13693(10) 0.0166(6) Uani 1 1 d . . . . .
H22 H 0.522191 0.644868 0.153586 0.020 Uiso 1 1 calc R U . . .
C23 C 0.55654(12) 0.4238(3) 0.09958(11) 0.0267(6) Uani 1 1 d . . . . .
H23A H 0.509150 0.420682 0.062080 0.040 Uiso 1 1 calc R U . . .
H23B H 0.558152 0.312977 0.132197 0.040 Uiso 1 1 calc R U . . .
H23C H 0.596674 0.406082 0.080439 0.040 Uiso 1 1 calc R U . . .
C24 C 0.56331(12) 0.8061(3) 0.08792(11) 0.0287(6) Uani 1 1 d . . . . .
H24A H 0.604613 0.793653 0.070086 0.043 Uiso 1 1 calc R U . . .
H24B H 0.567265 0.935688 0.112863 0.043 Uiso 1 1 calc R U . . .
H24C H 0.516752 0.802928 0.049377 0.043 Uiso 1 1 calc R U . . .
C25 C 0.68723(10) 0.6149(3) 0.39766(10) 0.0173(6) Uani 1 1 d . . . . .
H25A H 0.635194 0.648442 0.393665 0.021 Uiso 1 1 calc R U . . .
C26 C 0.73730(13) 0.7688(3) 0.44736(11) 0.0328(7) Uani 1 1 d . . . . .
H26A H 0.788913 0.736669 0.453576 0.049 Uiso 1 1 calc R U . . .
H26B H 0.729155 0.761648 0.492040 0.049 Uiso 1 1 calc R U . . .
H26C H 0.725933 0.906958 0.428341 0.049 Uiso 1 1 calc R U . . .
C27 C 0.70304(12) 0.3979(3) 0.42629(11) 0.0261(6) Uani 1 1 d . . . . .
H27A H 0.670982 0.301395 0.393383 0.039 Uiso 1 1 calc R U . . .
H27B H 0.693572 0.389424 0.470342 0.039 Uiso 1 1 calc R U . . .
H27C H 0.754718 0.363796 0.433503 0.039 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
O1 C1 1.232(2) . ?
N1 C1 1.379(2) . ?
N1 C3 1.394(2) . ?
N1 C16 1.441(2) . ?
N2 C1 1.388(2) . ?
N2 C2 1.402(2) . ?
N2 C4 1.435(2) . ?
C2 C3 1.339(3) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C5 1.400(3) . ?
C4 C9 1.404(3) . ?
C5 C6 1.398(3) . ?
C5 C10 1.511(3) . ?
C6 C7 1.380(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.378(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.394(3) . ?
C8 H8 0.9500 . ?
C9 C13 1.511(3) . ?
C10 C11 1.522(3) . ?
C10 C12 1.524(3) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.521(3) . ?
C13 C15 1.544(3) . ?
C13 H13A 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.399(3) . ?
C16 C21 1.400(3) . ?
C17 C18 1.395(2) . ?
C17 C22 1.516(3) . ?
C18 C19 1.380(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.394(2) . ?
C20 H20 0.9500 . ?
C21 C25 1.517(3) . ?
C22 C23 1.525(3) . ?
C22 C24 1.529(3) . ?
C22 H22 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C27 1.528(3) . ?
C25 C26 1.528(3) . ?
C25 H25A 1.0000 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

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
C1 N1 C3 110.82(14) . . ?
C1 N1 C16 122.28(14) . . ?
C3 N1 C16 126.46(14) . . ?
C1 N2 C2 109.74(14) . . ?
C1 N2 C4 124.46(14) . . ?
C2 N2 C4 125.68(14) . . ?
O1 C1 N1 128.59(15) . . ?
O1 C1 N2 127.14(15) . . ?
N1 C1 N2 104.27(14) . . ?
C3 C2 N2 107.93(15) . . ?
C3 C2 H2 126.0 . . ?
N2 C2 H2 126.0 . . ?
C2 C3 N1 107.22(15) . . ?
C2 C3 H3 126.4 . . ?
N1 C3 H3 126.4 . . ?
C5 C4 C9 122.68(16) . . ?
C5 C4 N2 119.12(16) . . ?
C9 C4 N2 118.20(16) . . ?
C6 C5 C4 117.25(17) . . ?
C6 C5 C10 120.97(17) . . ?
C4 C5 C10 121.77(16) . . ?
C7 C6 C5 121.16(19) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C8 C7 C6 120.26(18) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 121.36(18) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C4 117.17(18) . . ?
C8 C9 C13 121.93(17) . . ?
C4 C9 C13 120.75(16) . . ?
C5 C10 C11 112.10(17) . . ?
C5 C10 C12 111.03(16) . . ?
C11 C10 C12 111.01(18) . . ?
C5 C10 H10 107.5 . . ?
C11 C10 H10 107.5 . . ?
C12 C10 H10 107.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 C14 113.97(17) . . ?
C9 C13 C15 108.80(17) . . ?
C14 C13 C15 109.89(18) . . ?
C9 C13 H13A 108.0 . . ?
C14 C13 H13A 108.0 . . ?
C15 C13 H13A 108.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 122.86(15) . . ?
C17 C16 N1 118.37(15) . . ?
C21 C16 N1 118.75(15) . . ?
C18 C17 C16 117.00(17) . . ?
C18 C17 C22 121.44(16) . . ?
C16 C17 C22 121.56(15) . . ?
C19 C18 C17 121.66(17) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C20 119.79(16) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C21 121.30(17) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C16 117.33(16) . . ?
C20 C21 C25 121.30(17) . . ?
C16 C21 C25 121.35(15) . . ?
C17 C22 C23 111.21(15) . . ?
C17 C22 C24 112.01(15) . . ?
C23 C22 C24 111.27(16) . . ?
C17 C22 H22 107.4 . . ?
C23 C22 H22 107.4 . . ?
C24 C22 H22 107.4 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C25 C27 110.65(15) . . ?
C21 C25 C26 112.37(15) . . ?
C27 C25 C26 110.73(17) . . ?
C21 C25 H25A 107.6 . . ?
C27 C25 H25A 107.6 . . ?
C26 C25 H25A 107.6 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.044


_exptl_crystal_preparation       
'The refinement made use of aspherical scattering factors'
