#------------------------------------------------------------------------------
#$Date: 2020-03-04 02:27:54 +0200 (Wed, 04 Mar 2020) $
#$Revision: 248679 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/80/4038005.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4038005
loop_
_publ_author_name
'Duong, Adam'
'Levesque, Alexandre'
'Homand, Clara'
'Maris, Thierry'
'Wuest, James D.'
_publ_section_title
;
 Controlling Molecular Organization by Using Phenyl Embraces of Multiple
 Trityl Groups.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02974
_journal_year                    2020
_chemical_formula_moiety         'C26 H19 N'
_chemical_formula_sum            'C26 H19 N'
_chemical_formula_weight         345.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-11-24
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.5055(2)
_cell_length_b                   34.3595(4)
_cell_length_c                   7.1650(1)
_cell_measurement_reflns_used    9825
_cell_measurement_temperature    150
_cell_measurement_theta_max      67.779
_cell_measurement_theta_min      2.572
_cell_volume                     3817.23(9)
_computing_cell_refinement       'SAINT v7.46A (Bruker, 2008)'
_computing_data_collection       'APEX2 v2.1-0 (Bruker AXS, 2006a)'
_computing_data_reduction        'SAINT v7.46A (Bruker, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2004)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Microstar'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Helios optics'
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            56550
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.203
_diffrn_reflns_theta_min         2.572
_exptl_absorpt_coefficient_mu    0.529
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_correction_T_min  0.8822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3492
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0335
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0546P)²+0.3786P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0935
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2933
_reflns_number_total             3492
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b02974_si_003.cif
_cod_data_source_block           jw1362
_cod_database_code               4038005
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23),
  C24(H24), C25(H25), C26(H26)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, z-1/2'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.15267(8) 0.00236(3) 0.67927(17) 0.0413(3) Uani 1 1 d . . . . .
H1 H 1.1731 -0.0170 0.7632 0.050 Uiso 1 1 calc R . . . .
C2 C 1.07616(9) 0.02014(4) 0.71800(19) 0.0519(3) Uani 1 1 d . . . . .
H2 H 1.0445 0.0133 0.8267 0.062 Uiso 1 1 calc R . . . .
C3 C 1.04544(9) 0.04813(4) 0.59725(18) 0.0500(3) Uani 1 1 d . . . . .
H3 H 0.9923 0.0609 0.6219 0.060 Uiso 1 1 calc R . . . .
C4 C 1.09259(7) 0.05737(3) 0.44068(15) 0.0319(2) Uani 1 1 d . . . . .
C5 C 1.16956(8) 0.03781(4) 0.41490(18) 0.0495(3) Uani 1 1 d . . . . .
H5 H 1.2030 0.0441 0.3080 0.059 Uiso 1 1 calc R . . . .
C6 C 1.06321(7) 0.08558(3) 0.30717(15) 0.0339(2) Uani 1 1 d . . . . .
C7 C 1.03693(7) 0.10852(3) 0.19562(15) 0.0324(2) Uani 1 1 d . . . . .
C8 C 1.00086(7) 0.13709(3) 0.06237(14) 0.0300(2) Uani 1 1 d . . . . .
C9 C 0.95123(7) 0.16737(3) 0.18071(15) 0.0315(2) Uani 1 1 d . . . . .
C10 C 0.99492(8) 0.18691(3) 0.32317(16) 0.0389(3) Uani 1 1 d . . . . .
H10 H 1.0544 0.1819 0.3434 0.047 Uiso 1 1 calc R . . . .
C11 C 0.95225(9) 0.21344(3) 0.43494(17) 0.0457(3) Uani 1 1 d . . . . .
H11 H 0.9828 0.2267 0.5308 0.055 Uiso 1 1 calc R . . . .
C12 C 0.86526(9) 0.22088(3) 0.40828(18) 0.0478(3) Uani 1 1 d . . . . .
H12 H 0.8362 0.2393 0.4846 0.057 Uiso 1 1 calc R . . . .
C13 C 0.82152(8) 0.20134(3) 0.27032(17) 0.0447(3) Uani 1 1 d . . . . .
H13 H 0.7617 0.2060 0.2527 0.054 Uiso 1 1 calc R . . . .
C14 C 0.86383(7) 0.17481(3) 0.15642(16) 0.0368(3) Uani 1 1 d . . . . .
H14 H 0.8328 0.1616 0.0611 0.044 Uiso 1 1 calc R . . . .
C15 C 0.93990(6) 0.11640(3) -0.07589(14) 0.0295(2) Uani 1 1 d . . . . .
C16 C 0.90474(7) 0.08015(3) -0.03678(15) 0.0341(3) Uani 1 1 d . . . . .
H16 H 0.9196 0.0672 0.0760 0.041 Uiso 1 1 calc R . . . .
C17 C 0.84811(7) 0.06259(3) -0.16052(17) 0.0413(3) Uani 1 1 d . . . . .
H17 H 0.8251 0.0376 -0.1327 0.050 Uiso 1 1 calc R . . . .
C18 C 0.82486(7) 0.08115(4) -0.32385(17) 0.0423(3) Uani 1 1 d . . . . .
H18 H 0.7857 0.0691 -0.4080 0.051 Uiso 1 1 calc R . . . .
C19 C 0.85919(7) 0.11741(3) -0.36398(16) 0.0398(3) Uani 1 1 d . . . . .
H19 H 0.8433 0.1304 -0.4758 0.048 Uiso 1 1 calc R . . . .
C20 C 0.91659(7) 0.13469(3) -0.24160(16) 0.0355(3) Uani 1 1 d . . . . .
H20 H 0.9404 0.1594 -0.2711 0.043 Uiso 1 1 calc R . . . .
C21 C 1.07555(7) 0.15557(3) -0.04965(15) 0.0331(2) Uani 1 1 d . . . . .
C22 C 1.07741(7) 0.19487(4) -0.09285(17) 0.0414(3) Uani 1 1 d . . . . .
H22 H 1.0339 0.2116 -0.0454 0.050 Uiso 1 1 calc R . . . .
C23 C 1.14259(9) 0.20997(4) -0.20534(19) 0.0508(3) Uani 1 1 d . . . . .
H23 H 1.1431 0.2370 -0.2343 0.061 Uiso 1 1 calc R . . . .
C24 C 1.20605(9) 0.18612(4) -0.27472(19) 0.0543(4) Uani 1 1 d . . . . .
H24 H 1.2504 0.1965 -0.3515 0.065 Uiso 1 1 calc R . . . .
C25 C 1.20482(8) 0.14685(4) -0.23172(19) 0.0530(3) Uani 1 1 d . . . . .
H25 H 1.2486 0.1302 -0.2791 0.064 Uiso 1 1 calc R . . . .
C26 C 1.14041(7) 0.13175(4) -0.12052(17) 0.0421(3) Uani 1 1 d . . . . .
H26 H 1.1403 0.1047 -0.0919 0.051 Uiso 1 1 calc R . . . .
N1 N 1.19997(7) 0.01067(3) 0.53032(17) 0.0558(3) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1 118.4 . . ?
N1 C1 H1 118.4 . . ?
N1 C1 C2 123.27(11) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.06(12) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.27(11) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 117.11(10) . . ?
C3 C4 C6 122.01(10) . . ?
C5 C4 C6 120.87(10) . . ?
C4 C5 H5 117.9 . . ?
N1 C5 C4 124.25(11) . . ?
N1 C5 H5 117.9 . . ?
C7 C6 C4 178.37(12) . . ?
C6 C7 C8 177.48(11) . . ?
C7 C8 C9 106.29(8) . . ?
C7 C8 C15 109.89(8) . . ?
C7 C8 C21 108.94(8) . . ?
C15 C8 C9 110.91(8) . . ?
C15 C8 C21 108.36(8) . . ?
C21 C8 C9 112.41(8) . . ?
C10 C9 C8 118.84(10) . . ?
C14 C9 C8 122.69(9) . . ?
C14 C9 C10 118.41(10) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.55(11) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.50(12) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.31(11) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.69(12) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.53(11) . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C8 121.63(9) . . ?
C16 C15 C20 118.40(10) . . ?
C20 C15 C8 119.93(9) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.68(10) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.44(11) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.3 . . ?
C17 C18 C19 119.41(11) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.13(11) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 H20 119.5 . . ?
C19 C20 C15 120.94(10) . . ?
C19 C20 H20 119.5 . . ?
C22 C21 C8 122.14(10) . . ?
C22 C21 C26 118.44(10) . . ?
C26 C21 C8 119.28(10) . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.49(12) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 119.8 . . ?
C24 C23 C22 120.46(12) . . ?
C24 C23 H23 119.8 . . ?
C23 C24 H24 120.3 . . ?
C23 C24 C25 119.40(12) . . ?
C25 C24 H24 120.3 . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.37(12) . . ?
C26 C25 H25 119.8 . . ?
C21 C26 H26 119.6 . . ?
C25 C26 C21 120.83(12) . . ?
C25 C26 H26 119.6 . . ?
C1 N1 C5 117.03(10) . . ?
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 H1 0.9500 . ?
C1 C2 1.3630(17) . ?
C1 N1 1.3260(16) . ?
C2 H2 0.9500 . ?
C2 C3 1.3785(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.3761(16) . ?
C4 C5 1.3821(16) . ?
C4 C6 1.4360(15) . ?
C5 H5 0.9500 . ?
C5 N1 1.3326(15) . ?
C6 C7 1.1942(15) . ?
C7 C8 1.4793(14) . ?
C8 C9 1.5471(14) . ?
C8 C15 1.5428(14) . ?
C8 C21 1.5454(14) . ?
C9 C10 1.3970(16) . ?
C9 C14 1.3901(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.3821(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.3860(19) . ?
C12 H12 0.9500 . ?
C12 C13 1.3740(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.3882(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.3881(15) . ?
C15 C20 1.3912(15) . ?
C16 H16 0.9500 . ?
C16 C17 1.3860(16) . ?
C17 H17 0.9500 . ?
C17 C18 1.3806(17) . ?
C18 H18 0.9500 . ?
C18 C19 1.3850(17) . ?
C19 H19 0.9500 . ?
C19 C20 1.3834(16) . ?
C20 H20 0.9500 . ?
C21 C22 1.3855(16) . ?
C21 C26 1.3926(16) . ?
C22 H22 0.9500 . ?
C22 C23 1.3930(17) . ?
C23 H23 0.9500 . ?
C23 C24 1.374(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.384(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.3789(17) . ?
C26 H26 0.9500 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.1(2) . . . . ?
C2 C1 N1 C5 -0.2(2) . . . . ?
C2 C3 C4 C5 -0.51(19) . . . . ?
C2 C3 C4 C6 178.51(12) . . . . ?
C3 C4 C5 N1 0.6(2) . . . . ?
C4 C5 N1 C1 -0.3(2) . . . . ?
C6 C4 C5 N1 -178.41(13) . . . . ?
C7 C8 C9 C10 55.90(12) . . . . ?
C7 C8 C9 C14 -121.33(10) . . . . ?
C7 C8 C15 C16 19.28(13) . . . . ?
C7 C8 C15 C20 -162.96(9) . . . . ?
C7 C8 C21 C22 -139.65(11) . . . . ?
C7 C8 C21 C26 44.69(13) . . . . ?
C8 C9 C10 C11 -178.37(10) . . . . ?
C8 C9 C14 C13 177.85(10) . . . . ?
C8 C15 C16 C17 178.09(10) . . . . ?
C8 C15 C20 C19 -177.27(10) . . . . ?
C8 C21 C22 C23 -175.39(11) . . . . ?
C8 C21 C26 C25 175.56(11) . . . . ?
C9 C8 C15 C16 -97.96(11) . . . . ?
C9 C8 C15 C20 79.80(11) . . . . ?
C9 C8 C21 C22 -22.11(14) . . . . ?
C9 C8 C21 C26 162.23(10) . . . . ?
C9 C10 C11 C12 0.47(17) . . . . ?
C10 C9 C14 C13 0.60(15) . . . . ?
C10 C11 C12 C13 0.53(17) . . . . ?
C11 C12 C13 C14 -0.95(18) . . . . ?
C12 C13 C14 C9 0.38(17) . . . . ?
C14 C9 C10 C11 -1.02(15) . . . . ?
C15 C8 C9 C10 175.32(9) . . . . ?
C15 C8 C9 C14 -1.91(13) . . . . ?
C15 C8 C21 C22 100.82(11) . . . . ?
C15 C8 C21 C26 -74.84(12) . . . . ?
C15 C16 C17 C18 -0.84(17) . . . . ?
C16 C15 C20 C19 0.56(16) . . . . ?
C16 C17 C18 C19 0.52(18) . . . . ?
C17 C18 C19 C20 0.34(17) . . . . ?
C18 C19 C20 C15 -0.89(17) . . . . ?
C20 C15 C16 C17 0.30(16) . . . . ?
C21 C8 C9 C10 -63.19(12) . . . . ?
C21 C8 C9 C14 119.57(11) . . . . ?
C21 C8 C15 C16 138.21(10) . . . . ?
C21 C8 C15 C20 -44.02(12) . . . . ?
C21 C22 C23 C24 -0.14(19) . . . . ?
C22 C21 C26 C25 -0.26(17) . . . . ?
C22 C23 C24 C25 -0.1(2) . . . . ?
C23 C24 C25 C26 0.1(2) . . . . ?
C24 C25 C26 C21 0.1(2) . . . . ?
C26 C21 C22 C23 0.30(17) . . . . ?
N1 C1 C2 C3 0.2(2) . . . . ?
