# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_Mora_BIP_CH2NEt2
_audit_block_doi                 10.5517/ccdc.csd.cc2424ky
_database_code_depnum_ccdc_archive 'CCDC 1968269'
loop_
_audit_author_name
_audit_author_address
'Thomas L. Groy'
;Arizona State University
United States of America
;
_audit_update_record             
;
2019-11-26 deposited with the CCDC.	2020-03-31 downloaded from the CCDC.
;
_chemical_name_systematic        
2-(3?,5?-Di-tert-butyl-2?-hydroxyphenyl)-4-diethylmethyleneaminebenzimidazole
_chemical_name_common            BIP_CH2NEt2
_chemical_formula_moiety         'C26 H37 N3 O'
_chemical_formula_sum            'C26 H37 N3 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         407.58

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.6311(6)
_cell_length_b                   19.6619(13)
_cell_length_c                   13.5410(9)
_cell_angle_alpha                90
_cell_angle_beta                 106.9770(10)
_cell_angle_gamma                90
_cell_volume                     2452.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5299
_cell_measurement_theta_min      2.3089
_cell_measurement_theta_max      24.9662
_cell_measurement_temperature    193.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_size_max          0.468
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.253
_exptl_crystal_density_diffrn    1.104
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888

_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      193.0(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scan'

_diffrn_detector_area_resol_mean 8.3330

_diffrn_reflns_number            19785
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         25.27
_diffrn_reflns_theta_full        25.27
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16

_refine_special_details          
;
;

_reflns_number_total             4461
_reflns_number_gt                3308
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0663
_refine_ls_wR_factor_gt          0.1850
_refine_ls_wR_factor_ref         0.2005
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.070
_refine_ls_number_reflns         4461
_refine_ls_number_parameters     292
_refine_ls_number_restraints     13
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1334P)²+0.1680P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.242
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2015.5.1.3'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXTL XT-2014/4'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.81818(14) 0.41881(8) 0.33275(11) 0.0463(4) Uani d . . . 1.0 . .
H H1 0.815(3) 0.4550(14) 0.378(2) 0.076(8) Uiso d . . . 1.0 . .
N N1 0.71320(17) 0.51631(8) 0.41836(12) 0.0392(4) Uani d . . . 1.0 . .
N N2 0.47826(18) 0.54182(8) 0.36188(12) 0.0355(4) Uani d . . . 1.0 . .
H H2 0.390(2) 0.5415(10) 0.3253(16) 0.039(6) Uiso d . . . 1.0 . .
N N3 0.24395(17) 0.63326(8) 0.34810(13) 0.0407(4) Uani d . . . 1.0 . .
C C1 0.6881(2) 0.41335(10) 0.25996(15) 0.0367(5) Uani d . . . 1.0 . .
C C2 0.6681(2) 0.36374(10) 0.18164(15) 0.0387(5) Uani d . . . 1.0 . .
C C3 0.5374(2) 0.36357(10) 0.10444(15) 0.0383(5) Uani d . . . 1.0 . .
H H3 0.5244 0.331 0.0507 0.046 Uiso calc U . R 1.0 . .
C C4 0.4223(2) 0.40861(10) 0.10042(15) 0.0367(5) Uani d . . . 1.0 . .
C C5 0.4414(2) 0.45329(9) 0.18189(15) 0.0362(5) Uani d . . . 1.0 . .
H H5 0.364 0.4827 0.1837 0.043 Uiso calc U . R 1.0 . .
C C6 0.57162(19) 0.45637(9) 0.26182(14) 0.0346(4) Uani d . . . 1.0 . .
C C7 0.7900(2) 0.31275(11) 0.18130(16) 0.0463(5) Uani d . . . 1.0 . .
C C8 0.8364(3) 0.27325(13) 0.28406(19) 0.0647(7) Uani d . . . 1.0 . .
H H8A 0.8755 0.3051 0.3411 0.097 Uiso calc U . R 1.0 . .
H H8B 0.9111 0.2399 0.282 0.097 Uiso calc U . R 1.0 . .
H H8C 0.752 0.2497 0.2944 0.097 Uiso calc U . R 1.0 . .
C C9 0.9186(2) 0.35133(13) 0.16357(19) 0.0585(7) Uani d . . . 1.0 . .
H H9A 0.8879 0.3741 0.0963 0.088 Uiso calc U . R 1.0 . .
H H9B 0.9971 0.3193 0.165 0.088 Uiso calc U . R 1.0 . .
H H9C 0.9532 0.3854 0.2181 0.088 Uiso calc U . R 1.0 . .
C C10 0.7392(3) 0.25992(13) 0.0954(2) 0.0607(7) Uani d . . . 1.0 . .
H H10A 0.6532 0.2364 0.103 0.091 Uiso calc U . R 1.0 . .
H H10B 0.8169 0.2268 0.1 0.091 Uiso calc U . R 1.0 . .
H H10C 0.7149 0.2827 0.0281 0.091 Uiso calc U . R 1.0 . .
C C11 0.2864(2) 0.40753(10) 0.00775(16) 0.0432(5) Uani d . . . 1.0 . .
C C12 0.2162(3) 0.33707(13) -0.0040(2) 0.0619(7) Uani d . . . 1.0 . .
H H12A 0.2864 0.3029 -0.0119 0.093 Uiso calc U . R 1.0 . .
H H12B 0.1311 0.3365 -0.0651 0.093 Uiso calc U . R 1.0 . .
H H12C 0.1861 0.3266 0.0575 0.093 Uiso calc U . R 1.0 . .
C C13 0.3292(3) 0.42410(17) -0.09002(19) 0.0741(8) Uani d . . . 1.0 . .
H H13A 0.3708 0.4699 -0.0843 0.111 Uiso calc U . R 1.0 . .
H H13B 0.243 0.4219 -0.1502 0.111 Uiso calc U . R 1.0 . .
H H13C 0.4012 0.391 -0.0981 0.111 Uiso calc U . R 1.0 . .
C C14 0.1721(3) 0.45904(15) 0.0185(2) 0.0745(8) Uani d . . . 1.0 . .
H H14A 0.148 0.4504 0.0829 0.112 Uiso calc U . R 1.0 . .
H H14B 0.0845 0.4544 -0.0401 0.112 Uiso calc U . R 1.0 . .
H H14C 0.2108 0.5052 0.0197 0.112 Uiso calc U . R 1.0 . .
C C15 0.58904(19) 0.50400(10) 0.34647(14) 0.0356(5) Uani d . . . 1.0 . .
C C16 0.5349(2) 0.58063(9) 0.44918(14) 0.0354(5) Uani d . . . 1.0 . .
C C17 0.4686(2) 0.62780(10) 0.49779(16) 0.0392(5) Uani d . . . 1.0 . .
C C18 0.5593(2) 0.65788(11) 0.58502(16) 0.0471(5) Uani d . . . 1.0 . .
H H18 0.5204 0.6906 0.6212 0.057 Uiso calc U . R 1.0 . .
C C19 0.7070(3) 0.64156(11) 0.62182(18) 0.0510(6) Uani d . . . 1.0 . .
H H19 0.7648 0.663 0.6829 0.061 Uiso calc U . R 1.0 . .
C C20 0.7713(2) 0.59544(11) 0.57224(17) 0.0466(5) Uani d . . . 1.0 . .
H H20 0.872 0.5853 0.5972 0.056 Uiso calc U . R 1.0 . .
C C21 0.6821(2) 0.56437(10) 0.48379(15) 0.0390(5) Uani d . . . 1.0 . .
C C22 0.3074(2) 0.64173(10) 0.46020(16) 0.0423(5) Uani d . . . 1.0 . .
H H22A 0.2574 0.6106 0.4961 0.051 Uiso calc U . R 1.0 . .
H H22B 0.2895 0.6888 0.4792 0.051 Uiso calc U . R 1.0 . .
C C23 0.2965(3) 0.68617(11) 0.29132(17) 0.0507(6) Uani d . . . 1.0 . .
H H23A 0.4012 0.6938 0.3253 0.061 Uiso calc U . R 1.0 . .
H H23B 0.2448 0.7292 0.295 0.061 Uiso calc U . R 1.0 . .
C C24 0.2749(3) 0.66837(15) 0.17951(18) 0.0644(7) Uani d . . . 1.0 . .
H H24A 0.327 0.6262 0.1752 0.097 Uiso calc U . R 1.0 . .
H H24B 0.3125 0.7053 0.1459 0.097 Uiso calc U . R 1.0 . .
H H24C 0.1711 0.6621 0.1448 0.097 Uiso calc U . R 1.0 . .
C C25 0.0849(2) 0.63600(14) 0.3212(2) 0.0618(7) Uani d . P D 0.80(4) A 1
H H25A 0.045 0.6447 0.2462 0.074 Uiso calc U P R 0.80(4) A 1
H H25B 0.0565 0.6745 0.3582 0.074 Uiso calc U P R 0.80(4) A 1
C C26 0.0201(13) 0.5726(6) 0.3473(12) 0.098(3) Uani d U P D 0.80(4) A 1
H H26A 0.0392 0.535 0.3055 0.147 Uiso calc U P R 0.80(4) A 1
H H26B -0.0849 0.5786 0.3329 0.147 Uiso calc U P R 0.80(4) A 1
H H26C 0.0632 0.5623 0.4207 0.147 Uiso calc U P R 0.80(4) A 1
C C25' 0.0849(2) 0.63600(14) 0.3212(2) 0.0618(7) Uani d . P D 0.20(4) A 2
H H25C 0.0458 0.632 0.2452 0.074 Uiso calc U P R 0.20(4) A 2
H H25D 0.0574 0.6815 0.3406 0.074 Uiso calc U P R 0.20(4) A 2
C C26' 0.012(6) 0.584(2) 0.368(4) 0.098(3) Uani d U P D 0.20(4) A 2
H H26D 0.0655 0.5414 0.3758 0.147 Uiso calc U P R 0.20(4) A 2
H H26E -0.0875 0.5774 0.3237 0.147 Uiso calc U P R 0.20(4) A 2
H H26F 0.0091 0.6002 0.4363 0.147 Uiso calc U P R 0.20(4) A 2


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.353(2) ?
O1 H1 . 0.95(3) ?
N1 C15 . 1.325(2) ?
N1 C21 . 1.387(3) ?
N2 C15 . 1.366(2) ?
N2 C16 . 1.379(2) ?
N2 H2 . 0.85(2) ?
N3 C25' . 1.468(3) ?
N3 C25 . 1.468(3) ?
N3 C23 . 1.468(3) ?
N3 C22 . 1.471(3) ?
C1 C6 . 1.411(3) ?
C1 C2 . 1.412(3) ?
C2 C3 . 1.382(3) ?
C2 C7 . 1.545(3) ?
C3 C4 . 1.408(3) ?
C3 H3 . 0.95 ?
C4 C5 . 1.380(3) ?
C4 C11 . 1.526(3) ?
C5 C6 . 1.398(3) ?
C5 H5 . 0.95 ?
C6 C15 . 1.451(3) ?
C7 C10 . 1.529(3) ?
C7 C9 . 1.530(3) ?
C7 C8 . 1.541(3) ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C8 H8C . 0.98 ?
C9 H9A . 0.98 ?
C9 H9B . 0.98 ?
C9 H9C . 0.98 ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C11 C12 . 1.529(3) ?
C11 C13 . 1.532(3) ?
C11 C14 . 1.534(3) ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?
C16 C21 . 1.394(3) ?
C16 C17 . 1.395(3) ?
C17 C18 . 1.381(3) ?
C17 C22 . 1.511(3) ?
C18 C19 . 1.400(3) ?
C18 H18 . 0.95 ?
C19 C20 . 1.378(3) ?
C19 H19 . 0.95 ?
C20 C21 . 1.395(3) ?
C20 H20 . 0.95 ?
C22 H22A . 0.99 ?
C22 H22B . 0.99 ?
C23 C24 . 1.508(3) ?
C23 H23A . 0.99 ?
C23 H23B . 0.99 ?
C24 H24A . 0.98 ?
C24 H24B . 0.98 ?
C24 H24C . 0.98 ?
C25 C26 . 1.482(6) ?
C25 H25A . 0.99 ?
C25 H25B . 0.99 ?
C26 H26A . 0.98 ?
C26 H26B . 0.98 ?
C26 H26C . 0.98 ?
C25' C26' . 1.480(17) ?
C25' H25C . 0.99 ?
C25' H25D . 0.99 ?
C26' H26D . 0.98 ?
C26' H26E . 0.98 ?
C26' H26F . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 H1 . . 109.6(17) ?
C15 N1 C21 . . 106.06(16) ?
C15 N2 C16 . . 107.52(16) ?
C15 N2 H2 . . 126.8(14) ?
C16 N2 H2 . . 125.6(14) ?
C25' N3 C23 . . 109.76(17) ?
C25 N3 C23 . . 109.76(17) ?
C25' N3 C22 . . 109.92(16) ?
C25 N3 C22 . . 109.92(16) ?
C23 N3 C22 . . 110.94(16) ?
O1 C1 C6 . . 120.74(18) ?
O1 C1 C2 . . 119.74(17) ?
C6 C1 C2 . . 119.52(18) ?
C3 C2 C1 . . 117.65(18) ?
C3 C2 C7 . . 121.44(18) ?
C1 C2 C7 . . 120.89(18) ?
C2 C3 C4 . . 124.14(19) ?
C2 C3 H3 . . 117.9 ?
C4 C3 H3 . . 117.9 ?
C5 C4 C3 . . 116.74(18) ?
C5 C4 C11 . . 123.26(17) ?
C3 C4 C11 . . 119.98(18) ?
C4 C5 C6 . . 121.76(18) ?
C4 C5 H5 . . 119.1 ?
C6 C5 H5 . . 119.1 ?
C5 C6 C1 . . 119.89(18) ?
C5 C6 C15 . . 120.66(17) ?
C1 C6 C15 . . 119.45(17) ?
C10 C7 C9 . . 108.15(18) ?
C10 C7 C8 . . 106.8(2) ?
C9 C7 C8 . . 110.93(19) ?
C10 C7 C2 . . 111.61(18) ?
C9 C7 C2 . . 109.23(18) ?
C8 C7 C2 . . 110.14(17) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C7 C9 H9A . . 109.5 ?
C7 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C7 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C7 C10 H10A . . 109.5 ?
C7 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C7 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C4 C11 C12 . . 110.19(17) ?
C4 C11 C13 . . 108.98(17) ?
C12 C11 C13 . . 109.0(2) ?
C4 C11 C14 . . 112.30(18) ?
C12 C11 C14 . . 107.5(2) ?
C13 C11 C14 . . 108.9(2) ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C11 C13 H13A . . 109.5 ?
C11 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C11 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C11 C14 H14A . . 109.5 ?
C11 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C11 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
N1 C15 N2 . . 111.46(17) ?
N1 C15 C6 . . 124.71(17) ?
N2 C15 C6 . . 123.83(17) ?
N2 C16 C21 . . 105.70(17) ?
N2 C16 C17 . . 130.63(18) ?
C21 C16 C17 . . 123.67(18) ?
C18 C17 C16 . . 115.19(19) ?
C18 C17 C22 . . 122.83(19) ?
C16 C17 C22 . . 121.90(18) ?
C17 C18 C19 . . 122.0(2) ?
C17 C18 H18 . . 119.0 ?
C19 C18 H18 . . 119.0 ?
C20 C19 C18 . . 122.1(2) ?
C20 C19 H19 . . 118.9 ?
C18 C19 H19 . . 118.9 ?
C19 C20 C21 . . 117.0(2) ?
C19 C20 H20 . . 121.5 ?
C21 C20 H20 . . 121.5 ?
N1 C21 C16 . . 109.26(17) ?
N1 C21 C20 . . 130.77(19) ?
C16 C21 C20 . . 119.97(19) ?
N3 C22 C17 . . 113.80(16) ?
N3 C22 H22A . . 108.8 ?
C17 C22 H22A . . 108.8 ?
N3 C22 H22B . . 108.8 ?
C17 C22 H22B . . 108.8 ?
H22A C22 H22B . . 107.7 ?
N3 C23 C24 . . 113.19(19) ?
N3 C23 H23A . . 108.9 ?
C24 C23 H23A . . 108.9 ?
N3 C23 H23B . . 108.9 ?
C24 C23 H23B . . 108.9 ?
H23A C23 H23B . . 107.8 ?
C23 C24 H24A . . 109.5 ?
C23 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
C23 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
N3 C25 C26 . . 113.0(6) ?
N3 C25 H25A . . 109.0 ?
C26 C25 H25A . . 109.0 ?
N3 C25 H25B . . 109.0 ?
C26 C25 H25B . . 109.0 ?
H25A C25 H25B . . 107.8 ?
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 ?
N3 C25' C26' . . 117.(2) ?
N3 C25' H25C . . 107.9 ?
C26' C25' H25C . . 107.9 ?
N3 C25' H25D . . 107.9 ?
C26' C25' H25D . . 107.9 ?
H25C C25' H25D . . 107.2 ?
C25' C26' H26D . . 109.5 ?
C25' C26' H26E . . 109.5 ?
H26D C26' H26E . . 109.5 ?
C25' C26' H26F . . 109.5 ?
H26D C26' H26F . . 109.5 ?
H26E C26' H26F . . 109.5 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . -175.00(17) ?
C6 C1 C2 C3 . . . . 5.5(3) ?
O1 C1 C2 C7 . . . . 3.5(3) ?
C6 C1 C2 C7 . . . . -176.00(17) ?
C1 C2 C3 C4 . . . . -1.5(3) ?
C7 C2 C3 C4 . . . . 179.97(18) ?
C2 C3 C4 C5 . . . . -2.9(3) ?
C2 C3 C4 C11 . . . . 175.65(18) ?
C3 C4 C5 C6 . . . . 3.4(3) ?
C11 C4 C5 C6 . . . . -175.11(17) ?
C4 C5 C6 C1 . . . . 0.5(3) ?
C4 C5 C6 C15 . . . . 179.80(17) ?
O1 C1 C6 C5 . . . . 175.42(17) ?
C2 C1 C6 C5 . . . . -5.1(3) ?
O1 C1 C6 C15 . . . . -3.9(3) ?
C2 C1 C6 C15 . . . . 175.60(17) ?
C3 C2 C7 C10 . . . . -6.8(3) ?
C1 C2 C7 C10 . . . . 174.72(19) ?
C3 C2 C7 C9 . . . . 112.7(2) ?
C1 C2 C7 C9 . . . . -65.7(2) ?
C3 C2 C7 C8 . . . . -125.2(2) ?
C1 C2 C7 C8 . . . . 56.3(3) ?
C5 C4 C11 C12 . . . . -122.5(2) ?
C3 C4 C11 C12 . . . . 59.0(2) ?
C5 C4 C11 C13 . . . . 117.9(2) ?
C3 C4 C11 C13 . . . . -60.5(3) ?
C5 C4 C11 C14 . . . . -2.8(3) ?
C3 C4 C11 C14 . . . . 178.8(2) ?
C21 N1 C15 N2 . . . . 0.0(2) ?
C21 N1 C15 C6 . . . . -179.86(17) ?
C16 N2 C15 N1 . . . . -0.2(2) ?
C16 N2 C15 C6 . . . . 179.74(16) ?
C5 C6 C15 N1 . . . . -171.34(17) ?
C1 C6 C15 N1 . . . . 8.0(3) ?
C5 C6 C15 N2 . . . . 8.8(3) ?
C1 C6 C15 N2 . . . . -171.89(17) ?
C15 N2 C16 C21 . . . . 0.2(2) ?
C15 N2 C16 C17 . . . . 179.63(19) ?
N2 C16 C17 C18 . . . . -179.86(19) ?
C21 C16 C17 C18 . . . . -0.5(3) ?
N2 C16 C17 C22 . . . . 3.3(3) ?
C21 C16 C17 C22 . . . . -177.39(18) ?
C16 C17 C18 C19 . . . . -0.4(3) ?
C22 C17 C18 C19 . . . . 176.5(2) ?
C17 C18 C19 C20 . . . . 1.2(3) ?
C18 C19 C20 C21 . . . . -1.0(3) ?
C15 N1 C21 C16 . . . . 0.1(2) ?
C15 N1 C21 C20 . . . . 179.8(2) ?
N2 C16 C21 N1 . . . . -0.2(2) ?
C17 C16 C21 N1 . . . . -179.67(17) ?
N2 C16 C21 C20 . . . . -179.89(18) ?
C17 C16 C21 C20 . . . . 0.6(3) ?
C19 C20 C21 N1 . . . . -179.5(2) ?
C19 C20 C21 C16 . . . . 0.2(3) ?
C25' N3 C22 C17 . . . . 170.17(17) ?
C25 N3 C22 C17 . . . . 170.17(17) ?
C23 N3 C22 C17 . . . . -68.3(2) ?
C18 C17 C22 N3 . . . . 152.36(19) ?
C16 C17 C22 N3 . . . . -31.0(3) ?
C25' N3 C23 C24 . . . . -76.5(2) ?
C25 N3 C23 C24 . . . . -76.5(2) ?
C22 N3 C23 C24 . . . . 161.79(19) ?
C23 N3 C25 C26 . . . . 161.6(8) ?
C22 N3 C25 C26 . . . . -76.2(8) ?
C23 N3 C25' C26' . . . . 178.(3) ?
C22 N3 C25' C26' . . . . -60.(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2 N3 . 0.85(2) 2.36(2) 2.848(2) 116.8(17) ?
O1 H1 N1 . 0.95(3) 1.74(3) 2.593(2) 148.(3) ?


_chemical_properties_physical    Air-sensitive
####################################################################### 
# 
# 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_diBIP_imine_methoxy
_audit_block_doi                 10.5517/ccdc.csd.cc2424lz
_database_code_depnum_ccdc_archive 'CCDC 1968270'
loop_
_audit_author_name
_audit_author_address
'Thomas L. Groy'
;Arizona State University
United States of America
;
_audit_update_record             
;
2019-11-26 deposited with the CCDC.	2020-03-31 downloaded from the CCDC.
;
_chemical_name_systematic        
7-(4-Methoxyphenyliminomethyl-1H-benzimidazole-2-yl)-2-(3,5-di-tert-butyl-2-hydroxyphenyl-1-yl)-1H-benzimidazole
_chemical_name_common            diBIP-Imine-OMe
_chemical_formula_moiety         '2(C36 H37 N5 O2), C H2 Cl2 [+ solvent]'
_chemical_formula_sum            'C73 H76 Cl2 N10 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         1228.33

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   33.136(4)
_cell_length_b                   6.8671(8)
_cell_length_c                   30.967(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.031(2)
_cell_angle_gamma                90
_cell_volume                     6938.8(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3568
_cell_measurement_theta_min      2.4968
_cell_measurement_theta_max      24.9180
_cell_measurement_temperature    123.(2)

_exptl_crystal_description       'long thin plate'
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_size_max          0.514
_exptl_crystal_size_mid          0.199
_exptl_crystal_size_min          0.063
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2600

_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      123.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'sealed tube'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker Smart APEX Diffractometer'
_diffrn_measurement_method       'ω and φ scans'

_diffrn_detector_area_resol_mean 8.3330

_diffrn_reflns_number            27063
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0732
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_full        25.38
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       37

_refine_special_details          
;
;

_reflns_number_total             6369
_reflns_number_gt                4424
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0667
_refine_ls_wR_factor_gt          0.1470
_refine_ls_wR_factor_ref         0.1607
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_number_reflns         6369
_refine_ls_number_parameters     410
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0302P)²+15.7348P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.262
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2015.5.1.3'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2014)'
_computing_structure_solution    'SHELXTL XT-2014/4'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XShell ver. 6.3.1 (Bruker AXS, 2004)'
_computing_publication_material  'Bruker APEX2 v2014.11-0 (Bruker-AXS, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.59098(6) 0.3754(3) 0.25925(6) 0.0329(5) Uani d . . . 1 . .
H H1 0.5706 0.3795 0.272 0.049 Uiso calc U . R 1 . .
O O2 0.32507(6) 0.1421(3) 0.63246(7) 0.0366(5) Uani d . . . 1 . .
N N1 0.54807(7) 0.3693(3) 0.32171(7) 0.0274(5) Uani d . . . 1 . .
N N2 0.57880(7) 0.3313(3) 0.39143(7) 0.0272(5) Uani d . . . 1 . .
H H2 0.5984 0.3159 0.4143 0.033 Uiso calc U . R 1 . .
N N3 0.57878(7) 0.2759(4) 0.48095(8) 0.0387(6) Uani d . . . 1 . .
N N4 0.51987(7) 0.2484(3) 0.50630(7) 0.0284(5) Uani d . . . 1 . .
H H4 0.4934 0.2508 0.5066 0.034 Uiso calc U . R 1 . .
N N5 0.47566(7) 0.1745(3) 0.57535(8) 0.0297(6) Uani d . . . 1 . .
C C1 0.62566(8) 0.3597(4) 0.28953(9) 0.0260(6) Uani d . . . 1 . .
C C2 0.66393(8) 0.3553(4) 0.27578(9) 0.0265(6) Uani d . . . 1 . .
C C3 0.69892(8) 0.3467(4) 0.30816(9) 0.0265(6) Uani d . . . 1 . .
H H3 0.7249 0.3447 0.2992 0.032 Uiso calc U . R 1 . .
C C4 0.69780(8) 0.3408(4) 0.35318(9) 0.0276(6) Uani d . . . 1 . .
C C5 0.65966(8) 0.3393(4) 0.36546(9) 0.0269(6) Uani d . . . 1 . .
H H5 0.658 0.3325 0.3957 0.032 Uiso calc U . R 1 . .
C C6 0.62361(8) 0.3476(4) 0.33462(9) 0.0256(6) Uani d . . . 1 . .
C C7 0.66700(8) 0.3612(4) 0.22673(9) 0.0290(6) Uani d . . . 1 . .
C C8 0.64907(10) 0.5537(5) 0.20608(10) 0.0392(8) Uani d . . . 1 . .
H H8A 0.6203 0.5649 0.2096 0.059 Uiso calc U . R 1 . .
H H8B 0.6508 0.5551 0.1748 0.059 Uiso calc U . R 1 . .
H H8C 0.6647 0.6635 0.2207 0.059 Uiso calc U . R 1 . .
C C9 0.64402(10) 0.1865(4) 0.20295(10) 0.0379(8) Uani d . . . 1 . .
H H9A 0.6567 0.0652 0.2152 0.057 Uiso calc U . R 1 . .
H H9B 0.6454 0.1932 0.1716 0.057 Uiso calc U . R 1 . .
H H9C 0.6153 0.1898 0.2068 0.057 Uiso calc U . R 1 . .
C C10 0.71141(9) 0.3483(5) 0.21913(9) 0.0358(7) Uani d . . . 1 . .
H H10A 0.727 0.4594 0.2332 0.054 Uiso calc U . R 1 . .
H H10B 0.7118 0.3505 0.1876 0.054 Uiso calc U . R 1 . .
H H10C 0.7238 0.2269 0.2318 0.054 Uiso calc U . R 1 . .
C C11 0.73797(8) 0.3379(4) 0.38684(9) 0.0319(7) Uani d . . . 1 . .
C C12 0.76137(10) 0.5271(5) 0.38220(12) 0.0463(9) Uani d . . . 1 . .
H H12A 0.7868 0.5286 0.4038 0.069 Uiso calc U . R 1 . .
H H12B 0.7443 0.6387 0.3872 0.069 Uiso calc U . R 1 . .
H H12C 0.768 0.535 0.3526 0.069 Uiso calc U . R 1 . .
C C13 0.76421(9) 0.1646(5) 0.37757(11) 0.0428(8) Uani d . . . 1 . .
H H13A 0.7697 0.1739 0.3476 0.064 Uiso calc U . R 1 . .
H H13B 0.7495 0.0431 0.3809 0.064 Uiso calc U . R 1 . .
H H13C 0.7902 0.1658 0.3983 0.064 Uiso calc U . R 1 . .
C C14 0.73015(10) 0.3227(6) 0.43388(10) 0.0503(9) Uani d . . . 1 . .
H H14A 0.7564 0.3203 0.4541 0.075 Uiso calc U . R 1 . .
H H14B 0.7149 0.2028 0.4372 0.075 Uiso calc U . R 1 . .
H H14C 0.7141 0.4353 0.4405 0.075 Uiso calc U . R 1 . .
C C15 0.58376(8) 0.3480(4) 0.34865(9) 0.0264(6) Uani d . . . 1 . .
C C16 0.53760(8) 0.3430(4) 0.39212(9) 0.0275(6) Uani d . . . 1 . .
C C17 0.51612(8) 0.3305(4) 0.42727(9) 0.0277(6) Uani d . . . 1 . .
C C18 0.47379(8) 0.3500(4) 0.41629(10) 0.0303(7) Uani d . . . 1 . .
H H18 0.4577 0.3428 0.4388 0.036 Uiso calc U . R 1 . .
C C19 0.45427(9) 0.3796(4) 0.37310(10) 0.0330(7) Uani d . . . 1 . .
H H19 0.4253 0.3945 0.3671 0.04 Uiso calc U . R 1 . .
C C20 0.47596(9) 0.3880(4) 0.33876(10) 0.0328(7) Uani d . . . 1 . .
H H20 0.4623 0.4067 0.3094 0.039 Uiso calc U . R 1 . .
C C21 0.51832(8) 0.3680(4) 0.34860(9) 0.0284(6) Uani d . . . 1 . .
C C22 0.53847(9) 0.2891(4) 0.47088(9) 0.0288(6) Uani d . . . 1 . .
C C23 0.58670(9) 0.2204(5) 0.52485(10) 0.0383(8) Uani d . . . 1 . .
C C24 0.62391(10) 0.1821(7) 0.55250(11) 0.0593(11) Uani d . . . 1 . .
H H24 0.6492 0.1918 0.5422 0.071 Uiso calc U . R 1 . .
C C25 0.62262(10) 0.1299(6) 0.59524(11) 0.0559(10) Uani d . . . 1 . .
H H25 0.6476 0.1039 0.6146 0.067 Uiso calc U . R 1 . .
C C26 0.58585(9) 0.1143(5) 0.61067(10) 0.0389(8) Uani d . . . 1 . .
H H26 0.5864 0.0777 0.6403 0.047 Uiso calc U . R 1 . .
C C27 0.54848(9) 0.1504(4) 0.58421(9) 0.0298(6) Uani d . . . 1 . .
C C28 0.55011(8) 0.2034(4) 0.54088(9) 0.0286(6) Uani d . . . 1 . .
C C29 0.50985(9) 0.1348(4) 0.60002(9) 0.0310(7) Uani d . . . 1 . .
H H29 0.5099 0.094 0.6294 0.037 Uiso calc U . R 1 . .
C C30 0.43882(9) 0.1650(4) 0.59272(9) 0.0296(6) Uani d . . . 1 . .
C C31 0.43656(9) 0.1733(4) 0.63707(9) 0.0300(7) Uani d . . . 1 . .
H H31 0.4611 0.1851 0.6579 0.036 Uiso calc U . R 1 . .
C C32 0.39957(9) 0.1648(4) 0.65165(9) 0.0301(7) Uani d . . . 1 . .
H H32 0.3989 0.1701 0.6822 0.036 Uiso calc U . R 1 . .
C C33 0.36327(9) 0.1483(4) 0.62165(10) 0.0311(7) Uani d . . . 1 . .
C C34 0.36505(9) 0.1414(5) 0.57714(10) 0.0412(8) Uani d . . . 1 . .
H H34 0.3405 0.1304 0.5563 0.049 Uiso calc U . R 1 . .
C C35 0.40226(9) 0.1504(5) 0.56296(10) 0.0394(8) Uani d . . . 1 . .
H H35 0.4029 0.1465 0.5324 0.047 Uiso calc U . R 1 . .
C C36 0.32307(9) 0.1481(4) 0.67814(10) 0.0360(7) Uani d . . . 1 . .
H H36A 0.3378 0.0363 0.6929 0.054 Uiso calc U . R 1 . .
H H36B 0.2943 0.1433 0.682 0.054 Uiso calc U . R 1 . .
H H36C 0.3356 0.269 0.6909 0.054 Uiso calc U . R 1 . .
Cl Cl1A 0.53785(3) 0.86035(17) 0.23211(3) 0.0682(3) Uani d . . . 1 . .
C C1A 0.5 1.0034(7) 0.25 0.0570(14) Uani d T P S 1 . .
H H1A1 0.487 1.0882 0.2257 0.068 Uiso calc U P R 0.5 . .
H H1A2 0.513 1.0882 0.2743 0.068 Uiso calc U P R 0.5 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.355(3) ?
O1 H1 . 0.84 ?
O2 C33 . 1.365(3) ?
O2 C36 . 1.428(3) ?
N1 C15 . 1.331(3) ?
N1 C21 . 1.397(3) ?
N2 C15 . 1.368(3) ?
N2 C16 . 1.371(3) ?
N2 H2 . 0.88 ?
N3 C22 . 1.321(4) ?
N3 C23 . 1.392(4) ?
N4 C28 . 1.368(3) ?
N4 C22 . 1.377(3) ?
N4 H4 . 0.88 ?
N5 C29 . 1.281(4) ?
N5 C30 . 1.419(4) ?
C1 C2 . 1.407(4) ?
C1 C6 . 1.412(4) ?
C2 C3 . 1.396(4) ?
C2 C7 . 1.540(4) ?
C3 C4 . 1.402(4) ?
C3 H3 . 0.95 ?
C4 C5 . 1.382(4) ?
C4 C11 . 1.541(4) ?
C5 C6 . 1.395(4) ?
C5 H5 . 0.95 ?
C6 C15 . 1.460(4) ?
C7 C10 . 1.533(4) ?
C7 C9 . 1.538(4) ?
C7 C8 . 1.542(4) ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C8 H8C . 0.98 ?
C9 H9A . 0.98 ?
C9 H9B . 0.98 ?
C9 H9C . 0.98 ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C11 C14 . 1.527(4) ?
C11 C13 . 1.530(4) ?
C11 C12 . 1.533(4) ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?
C16 C21 . 1.398(4) ?
C16 C17 . 1.403(4) ?
C17 C18 . 1.391(4) ?
C17 C22 . 1.451(4) ?
C18 C19 . 1.395(4) ?
C18 H18 . 0.95 ?
C19 C20 . 1.385(4) ?
C19 H19 . 0.95 ?
C20 C21 . 1.390(4) ?
C20 H20 . 0.95 ?
C23 C28 . 1.393(4) ?
C23 C24 . 1.398(4) ?
C24 C25 . 1.379(5) ?
C24 H24 . 0.95 ?
C25 C26 . 1.388(4) ?
C25 H25 . 0.95 ?
C26 C27 . 1.383(4) ?
C26 H26 . 0.95 ?
C27 C28 . 1.401(4) ?
C27 C29 . 1.452(4) ?
C29 H29 . 0.95 ?
C30 C31 . 1.390(4) ?
C30 C35 . 1.392(4) ?
C31 C32 . 1.379(4) ?
C31 H31 . 0.95 ?
C32 C33 . 1.390(4) ?
C32 H32 . 0.95 ?
C33 C34 . 1.391(4) ?
C34 C35 . 1.381(4) ?
C34 H34 . 0.95 ?
C35 H35 . 0.95 ?
C36 H36A . 0.98 ?
C36 H36B . 0.98 ?
C36 H36C . 0.98 ?
Cl1A C1A . 1.757(3) ?
C1A Cl1A 2_655 1.757(3) ?
C1A H1A1 . 0.99 ?
C1A H1A2 . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 H1 . . 109.5 ?
C33 O2 C36 . . 116.6(2) ?
C15 N1 C21 . . 105.5(2) ?
C15 N2 C16 . . 107.3(2) ?
C15 N2 H2 . . 126.3 ?
C16 N2 H2 . . 126.3 ?
C22 N3 C23 . . 105.1(2) ?
C28 N4 C22 . . 107.5(2) ?
C28 N4 H4 . . 126.3 ?
C22 N4 H4 . . 126.3 ?
C29 N5 C30 . . 119.6(2) ?
O1 C1 C2 . . 119.5(2) ?
O1 C1 C6 . . 120.5(2) ?
C2 C1 C6 . . 120.0(2) ?
C3 C2 C1 . . 117.6(2) ?
C3 C2 C7 . . 121.4(2) ?
C1 C2 C7 . . 121.1(2) ?
C2 C3 C4 . . 123.6(2) ?
C2 C3 H3 . . 118.2 ?
C4 C3 H3 . . 118.2 ?
C5 C4 C3 . . 117.3(3) ?
C5 C4 C11 . . 122.5(2) ?
C3 C4 C11 . . 120.2(2) ?
C4 C5 C6 . . 121.8(3) ?
C4 C5 H5 . . 119.1 ?
C6 C5 H5 . . 119.1 ?
C5 C6 C1 . . 119.8(2) ?
C5 C6 C15 . . 120.5(2) ?
C1 C6 C15 . . 119.7(2) ?
C10 C7 C9 . . 106.9(2) ?
C10 C7 C2 . . 112.3(2) ?
C9 C7 C2 . . 109.9(2) ?
C10 C7 C8 . . 107.2(2) ?
C9 C7 C8 . . 110.3(2) ?
C2 C7 C8 . . 110.1(2) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C7 C9 H9A . . 109.5 ?
C7 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C7 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C7 C10 H10A . . 109.5 ?
C7 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C7 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C14 C11 C13 . . 108.8(3) ?
C14 C11 C12 . . 108.7(3) ?
C13 C11 C12 . . 109.2(2) ?
C14 C11 C4 . . 112.1(2) ?
C13 C11 C4 . . 109.6(2) ?
C12 C11 C4 . . 108.5(2) ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C11 C13 H13A . . 109.5 ?
C11 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C11 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C11 C14 H14A . . 109.5 ?
C11 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C11 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
N1 C15 N2 . . 111.9(2) ?
N1 C15 C6 . . 124.4(2) ?
N2 C15 C6 . . 123.7(2) ?
N2 C16 C21 . . 106.3(2) ?
N2 C16 C17 . . 130.5(3) ?
C21 C16 C17 . . 123.2(3) ?
C18 C17 C16 . . 115.5(3) ?
C18 C17 C22 . . 125.2(3) ?
C16 C17 C22 . . 119.2(2) ?
C17 C18 C19 . . 121.8(3) ?
C17 C18 H18 . . 119.1 ?
C19 C18 H18 . . 119.1 ?
C20 C19 C18 . . 121.7(3) ?
C20 C19 H19 . . 119.1 ?
C18 C19 H19 . . 119.1 ?
C19 C20 C21 . . 117.8(3) ?
C19 C20 H20 . . 121.1 ?
C21 C20 H20 . . 121.1 ?
C20 C21 N1 . . 131.2(3) ?
C20 C21 C16 . . 119.9(3) ?
N1 C21 C16 . . 108.9(2) ?
N3 C22 N4 . . 111.9(3) ?
N3 C22 C17 . . 124.4(3) ?
N4 C22 C17 . . 123.7(2) ?
N3 C23 C28 . . 110.1(3) ?
N3 C23 C24 . . 130.2(3) ?
C28 C23 C24 . . 119.7(3) ?
C25 C24 C23 . . 117.7(3) ?
C25 C24 H24 . . 121.1 ?
C23 C24 H24 . . 121.1 ?
C24 C25 C26 . . 121.8(3) ?
C24 C25 H25 . . 119.1 ?
C26 C25 H25 . . 119.1 ?
C27 C26 C25 . . 122.1(3) ?
C27 C26 H26 . . 119.0 ?
C25 C26 H26 . . 119.0 ?
C26 C27 C28 . . 115.7(3) ?
C26 C27 C29 . . 122.6(3) ?
C28 C27 C29 . . 121.7(3) ?
N4 C28 C23 . . 105.5(2) ?
N4 C28 C27 . . 131.5(3) ?
C23 C28 C27 . . 123.0(3) ?
N5 C29 C27 . . 121.6(3) ?
N5 C29 H29 . . 119.2 ?
C27 C29 H29 . . 119.2 ?
C31 C30 C35 . . 117.8(3) ?
C31 C30 N5 . . 124.8(3) ?
C35 C30 N5 . . 117.3(3) ?
C32 C31 C30 . . 121.7(3) ?
C32 C31 H31 . . 119.1 ?
C30 C31 H31 . . 119.1 ?
C31 C32 C33 . . 120.0(3) ?
C31 C32 H32 . . 120.0 ?
C33 C32 H32 . . 120.0 ?
O2 C33 C32 . . 124.7(3) ?
O2 C33 C34 . . 116.3(3) ?
C32 C33 C34 . . 118.9(3) ?
C35 C34 C33 . . 120.5(3) ?
C35 C34 H34 . . 119.7 ?
C33 C34 H34 . . 119.7 ?
C34 C35 C30 . . 121.0(3) ?
C34 C35 H35 . . 119.5 ?
C30 C35 H35 . . 119.5 ?
O2 C36 H36A . . 109.5 ?
O2 C36 H36B . . 109.5 ?
H36A C36 H36B . . 109.5 ?
O2 C36 H36C . . 109.5 ?
H36A C36 H36C . . 109.5 ?
H36B C36 H36C . . 109.5 ?
Cl1A C1A Cl1A . 2_655 112.0(3) ?
Cl1A C1A H1A1 . . 109.2 ?
Cl1A C1A H1A1 2_655 . 109.2 ?
Cl1A C1A H1A2 . . 109.2 ?
Cl1A C1A H1A2 2_655 . 109.2 ?
H1A1 C1A H1A2 . . 107.9 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . 177.5(2) ?
C6 C1 C2 C3 . . . . -2.5(4) ?
O1 C1 C2 C7 . . . . -2.1(4) ?
C6 C1 C2 C7 . . . . 177.9(2) ?
C1 C2 C3 C4 . . . . 0.5(4) ?
C7 C2 C3 C4 . . . . -179.9(2) ?
C2 C3 C4 C5 . . . . 1.4(4) ?
C2 C3 C4 C11 . . . . -178.1(2) ?
C3 C4 C5 C6 . . . . -1.4(4) ?
C11 C4 C5 C6 . . . . 178.1(3) ?
C4 C5 C6 C1 . . . . -0.6(4) ?
C4 C5 C6 C15 . . . . -179.3(3) ?
O1 C1 C6 C5 . . . . -177.4(2) ?
C2 C1 C6 C5 . . . . 2.5(4) ?
O1 C1 C6 C15 . . . . 1.3(4) ?
C2 C1 C6 C15 . . . . -178.7(2) ?
C3 C2 C7 C10 . . . . 2.2(4) ?
C1 C2 C7 C10 . . . . -178.1(3) ?
C3 C2 C7 C9 . . . . 121.0(3) ?
C1 C2 C7 C9 . . . . -59.3(3) ?
C3 C2 C7 C8 . . . . -117.2(3) ?
C1 C2 C7 C8 . . . . 62.4(3) ?
C5 C4 C11 C14 . . . . 2.9(4) ?
C3 C4 C11 C14 . . . . -177.6(3) ?
C5 C4 C11 C13 . . . . 123.9(3) ?
C3 C4 C11 C13 . . . . -56.7(3) ?
C5 C4 C11 C12 . . . . -117.0(3) ?
C3 C4 C11 C12 . . . . 62.4(3) ?
C21 N1 C15 N2 . . . . 0.6(3) ?
C21 N1 C15 C6 . . . . -177.9(3) ?
C16 N2 C15 N1 . . . . -0.2(3) ?
C16 N2 C15 C6 . . . . 178.3(3) ?
C5 C6 C15 N1 . . . . 175.1(3) ?
C1 C6 C15 N1 . . . . -3.6(4) ?
C5 C6 C15 N2 . . . . -3.2(4) ?
C1 C6 C15 N2 . . . . 178.0(2) ?
C15 N2 C16 C21 . . . . -0.3(3) ?
C15 N2 C16 C17 . . . . 178.6(3) ?
N2 C16 C17 C18 . . . . 179.6(3) ?
C21 C16 C17 C18 . . . . -1.7(4) ?
N2 C16 C17 C22 . . . . -3.5(5) ?
C21 C16 C17 C22 . . . . 175.1(3) ?
C16 C17 C18 C19 . . . . 0.1(4) ?
C22 C17 C18 C19 . . . . -176.5(3) ?
C17 C18 C19 C20 . . . . 1.1(4) ?
C18 C19 C20 C21 . . . . -0.8(4) ?
C19 C20 C21 N1 . . . . 179.8(3) ?
C19 C20 C21 C16 . . . . -0.8(4) ?
C15 N1 C21 C20 . . . . 178.8(3) ?
C15 N1 C21 C16 . . . . -0.7(3) ?
N2 C16 C21 C20 . . . . -179.0(3) ?
C17 C16 C21 C20 . . . . 2.1(4) ?
N2 C16 C21 N1 . . . . 0.6(3) ?
C17 C16 C21 N1 . . . . -178.4(2) ?
C23 N3 C22 N4 . . . . 1.1(3) ?
C23 N3 C22 C17 . . . . -175.6(3) ?
C28 N4 C22 N3 . . . . -1.0(3) ?
C28 N4 C22 C17 . . . . 175.7(3) ?
C18 C17 C22 N3 . . . . -178.2(3) ?
C16 C17 C22 N3 . . . . 5.3(4) ?
C18 C17 C22 N4 . . . . 5.4(4) ?
C16 C17 C22 N4 . . . . -171.1(3) ?
C22 N3 C23 C28 . . . . -0.8(4) ?
C22 N3 C23 C24 . . . . 179.0(4) ?
N3 C23 C24 C25 . . . . 179.7(4) ?
C28 C23 C24 C25 . . . . -0.5(6) ?
C23 C24 C25 C26 . . . . 0.3(6) ?
C24 C25 C26 C27 . . . . -0.1(6) ?
C25 C26 C27 C28 . . . . 0.1(5) ?
C25 C26 C27 C29 . . . . -179.9(3) ?
C22 N4 C28 C23 . . . . 0.5(3) ?
C22 N4 C28 C27 . . . . -179.7(3) ?
N3 C23 C28 N4 . . . . 0.2(3) ?
C24 C23 C28 N4 . . . . -179.6(3) ?
N3 C23 C28 C27 . . . . -179.7(3) ?
C24 C23 C28 C27 . . . . 0.5(5) ?
C26 C27 C28 N4 . . . . 179.8(3) ?
C29 C27 C28 N4 . . . . -0.1(5) ?
C26 C27 C28 C23 . . . . -0.3(4) ?
C29 C27 C28 C23 . . . . 179.7(3) ?
C30 N5 C29 C27 . . . . -177.4(2) ?
C26 C27 C29 N5 . . . . 177.9(3) ?
C28 C27 C29 N5 . . . . -2.2(4) ?
C29 N5 C30 C31 . . . . 20.4(4) ?
C29 N5 C30 C35 . . . . -160.9(3) ?
C35 C30 C31 C32 . . . . 0.9(4) ?
N5 C30 C31 C32 . . . . 179.5(3) ?
C30 C31 C32 C33 . . . . -0.3(4) ?
C36 O2 C33 C32 . . . . -1.7(4) ?
C36 O2 C33 C34 . . . . 179.7(3) ?
C31 C32 C33 O2 . . . . -178.8(3) ?
C31 C32 C33 C34 . . . . -0.2(4) ?
O2 C33 C34 C35 . . . . 178.8(3) ?
C32 C33 C34 C35 . . . . 0.1(5) ?
C33 C34 C35 C30 . . . . 0.5(5) ?
C31 C30 C35 C34 . . . . -1.0(5) ?
N5 C30 C35 C34 . . . . -179.7(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 N1 . 0.84 1.83 2.593(3) 151.0 ?
N2 H2 N3 . 0.88 2.29 2.798(3) 117.0 ?
N4 H4 N5 . 0.88 2.36 2.840(3) 114.3 ?
C20 H20 O1 2_655 0.95 2.53 3.434(3) 160.0 ?
C1A H1A2 N1 1_565 0.99 2.58 3.543(4) 165.5 ?
C1A H1A1 N1 2_665 0.99 2.58 3.543(4) 165.5 ?


# start Validation Reply Form
_vrf_PLAT934_diBIP_imine_methoxy 
;
PROBLEM: Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..        2 Check  
RESPONSE: Due to disordered solvent in large voids.
;
_vrf_PLAT340_diBIP_imine_methoxy 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00409 Ang.  
RESPONSE: Due to disordered solvent in large voids.
;
_vrf_PLAT906_diBIP_imine_methoxy 
;
PROBLEM: Large K Value in the Analysis of Variance ......    8.186 Check 
RESPONSE: Large K only in weakest data Fc/Fc(max) < 0.004
;
# end Validation Reply Form





_chemical_properties_physical    Moisture-sensitive
