#------------------------------------------------------------------------------
#$Date: 2020-09-23 00:57:31 +0300 (Wed, 23 Sep 2020) $
#$Revision: 256625 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/80/4518070.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_4518070
loop_
_publ_author_name
'Cole, Bren E.'
'Cheisson, Thibault'
'Nelson, Joshua J. M.'
'Higgins, Robert F.'
'Gau, Michael R.'
'Carroll, Patrick J.'
'Schelter, Eric J.'
_publ_section_title
;
 Understanding Molecular Factors That Determine Performance in the Rare
 Earth (TriNOx) Separations System
;
_journal_name_full               'ACS Sustainable Chemistry & Engineering'
_journal_paper_doi               10.1021/acssuschemeng.0c03974
_journal_year                    2020
_chemical_formula_moiety         'C39 H30 Br3 N'
_chemical_formula_sum            'C39 H30 Br3 N'
_chemical_formula_weight         752.37
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-06-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                102.267(7)
_cell_angle_beta                 92.880(7)
_cell_angle_gamma                94.271(6)
_cell_formula_units_Z            2
_cell_length_a                   9.3851(19)
_cell_length_b                   11.778(3)
_cell_length_c                   14.503(3)
_cell_measurement_reflns_used    9064
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.52
_cell_volume                     1558.6(6)
_computing_cell_refinement       'Bruker SAINT v8.34A'
_computing_data_collection       'Bruker APEX2 v2014.11-0'
_computing_data_reduction        'Bruker SAINT v8.34A'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device       'CCD area detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            38156
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.556
_diffrn_reflns_theta_min         1.440
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    3.912
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/4'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.717
_refine_diff_density_min         -0.831
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         7048
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0374
_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)+(0.0438P)²+1.6083P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0997
_reflns_number_gt                5459
_reflns_number_total             7048
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sc0c03974_si_002.cif
_cod_data_source_block           40271
_cod_database_code               4518070
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.799
_shelx_estimated_absorpt_t_min   0.673
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Br1 Br 0.70302(4) 0.07326(2) -0.03696(2) 0.02779(10) Uani 1 1 d . . . . .
Br2 Br 0.00585(4) 0.12430(3) 0.16745(3) 0.03483(11) Uani 1 1 d . . . . .
Br3 Br 0.64961(4) 0.06307(3) 0.37532(3) 0.03646(11) Uani 1 1 d . . . . .
N1 N 0.4579(3) 0.27521(19) 0.20256(17) 0.0173(5) Uani 1 1 d . . . . .
C1 C 0.5695(3) 0.2164(2) 0.1470(2) 0.0200(6) Uani 1 1 d . . . . .
H1a H 0.526609 0.141265 0.107697 0.027 Uiso 1 1 calc R . . . .
H1b H 0.645035 0.199165 0.190901 0.027 Uiso 1 1 calc R . . . .
C2 C 0.6369(3) 0.2884(2) 0.0838(2) 0.0173(6) Uani 1 1 d . . . . .
C3 C 0.7048(3) 0.2386(2) 0.0032(2) 0.0206(6) Uani 1 1 d . . . . .
C4 C 0.7745(3) 0.3057(3) -0.0511(2) 0.0234(7) Uani 1 1 d . . . . .
H4 H 0.817813 0.269260 -0.106273 0.031 Uiso 1 1 calc R . . . .
C5 C 0.7810(3) 0.4266(3) -0.0247(2) 0.0223(6) Uani 1 1 d . . . . .
H5 H 0.831267 0.472607 -0.061077 0.030 Uiso 1 1 calc R . . . .
C6 C 0.7144(3) 0.4812(2) 0.0548(2) 0.0186(6) Uani 1 1 d . . . . .
C7 C 0.6427(3) 0.4104(2) 0.1076(2) 0.0186(6) Uani 1 1 d . . . . .
H7 H 0.596453 0.446600 0.161550 0.025 Uiso 1 1 calc R . . . .
C8 C 0.7192(3) 0.6105(2) 0.0821(2) 0.0189(6) Uani 1 1 d . . . . .
C9 C 0.8407(3) 0.6800(3) 0.0669(2) 0.0230(7) Uani 1 1 d . . . . .
H9 H 0.920288 0.643799 0.039539 0.031 Uiso 1 1 calc R . . . .
C10 C 0.8453(4) 0.8011(3) 0.0915(2) 0.0270(7) Uani 1 1 d . . . . .
H10 H 0.928575 0.846322 0.080839 0.036 Uiso 1 1 calc R . . . .
C11 C 0.7321(4) 0.8568(3) 0.1308(2) 0.0254(7) Uani 1 1 d . . . . .
H11 H 0.736688 0.939520 0.147405 0.034 Uiso 1 1 calc R . . . .
C12 C 0.6088(4) 0.7884(3) 0.1459(2) 0.0250(7) Uani 1 1 d . . . . .
H12 H 0.529069 0.825084 0.172616 0.033 Uiso 1 1 calc R . . . .
C13 C 0.6042(3) 0.6670(2) 0.1217(2) 0.0217(6) Uani 1 1 d . . . . .
H13 H 0.521025 0.621871 0.132476 0.029 Uiso 1 1 calc R . . . .
C14 C 0.3200(3) 0.2519(2) 0.1463(2) 0.0217(6) Uani 1 1 d . . . . .
H14a H 0.285122 0.168876 0.139323 0.029 Uiso 1 1 calc R . . . .
H14b H 0.334087 0.265941 0.082345 0.029 Uiso 1 1 calc R . . . .
C15 C 0.2086(3) 0.3276(2) 0.1912(2) 0.0199(6) Uani 1 1 d . . . . .
C16 C 0.0681(3) 0.2863(2) 0.2029(2) 0.0214(6) Uani 1 1 d . . . . .
C17 C -0.0318(3) 0.3608(3) 0.2420(2) 0.0254(7) Uani 1 1 d . . . . .
H17 H -0.126178 0.330467 0.249441 0.034 Uiso 1 1 calc R . . . .
C18 C 0.0071(3) 0.4798(3) 0.2702(2) 0.0231(7) Uani 1 1 d . . . . .
H18 H -0.061409 0.530608 0.296605 0.031 Uiso 1 1 calc R . . . .
C19 C 0.1465(3) 0.5259(2) 0.2601(2) 0.0196(6) Uani 1 1 d . . . . .
C20 C 0.2440(3) 0.4483(2) 0.2212(2) 0.0203(6) Uani 1 1 d . . . . .
H20 H 0.338744 0.478572 0.214762 0.027 Uiso 1 1 calc R . . . .
C21 C 0.1877(3) 0.6533(2) 0.2892(2) 0.0207(6) Uani 1 1 d . . . . .
C22 C 0.3279(4) 0.6962(3) 0.3230(2) 0.0266(7) Uani 1 1 d . . . . .
H22 H 0.397865 0.643064 0.327722 0.035 Uiso 1 1 calc R . . . .
C23 C 0.3663(4) 0.8155(3) 0.3499(3) 0.0334(8) Uani 1 1 d . . . . .
H23 H 0.461645 0.843129 0.373517 0.044 Uiso 1 1 calc R . . . .
C24 C 0.2658(4) 0.8944(3) 0.3424(3) 0.0355(9) Uani 1 1 d . . . . .
H24 H 0.292883 0.975831 0.359680 0.047 Uiso 1 1 calc R . . . .
C25 C 0.1263(4) 0.8542(3) 0.3097(3) 0.0322(8) Uani 1 1 d . . . . .
H25 H 0.057264 0.908014 0.304702 0.043 Uiso 1 1 calc R . . . .
C26 C 0.0870(4) 0.7341(3) 0.2839(2) 0.0264(7) Uani 1 1 d . . . . .
H26 H -0.009368 0.706990 0.262464 0.035 Uiso 1 1 calc R . . . .
C27 C 0.4480(3) 0.2380(2) 0.2929(2) 0.0212(6) Uani 1 1 d . . . . .
H27a H 0.444536 0.151906 0.281470 0.028 Uiso 1 1 calc R . . . .
H27b H 0.358834 0.262688 0.321847 0.028 Uiso 1 1 calc R . . . .
C28 C 0.5758(3) 0.2914(2) 0.3594(2) 0.0200(6) Uani 1 1 d . . . . .
C29 C 0.6713(3) 0.2289(2) 0.4008(2) 0.0226(7) Uani 1 1 d . . . . .
C30 C 0.7877(3) 0.2843(3) 0.4610(2) 0.0239(7) Uani 1 1 d . . . . .
H30 H 0.850126 0.239734 0.489429 0.032 Uiso 1 1 calc R . . . .
C31 C 0.8122(3) 0.4044(3) 0.4791(2) 0.0221(6) Uani 1 1 d . . . . .
H31 H 0.892088 0.441994 0.519902 0.029 Uiso 1 1 calc R . . . .
C32 C 0.7203(3) 0.4714(2) 0.4381(2) 0.0188(6) Uani 1 1 d . . . . .
C33 C 0.6038(3) 0.4134(2) 0.3802(2) 0.0201(6) Uani 1 1 d . . . . .
H33 H 0.539793 0.458240 0.353308 0.027 Uiso 1 1 calc R . . . .
C34 C 0.7513(3) 0.6000(2) 0.4535(2) 0.0204(6) Uani 1 1 d . . . . .
C35 C 0.7221(3) 0.6587(3) 0.3808(2) 0.0224(6) Uani 1 1 d . . . . .
H35 H 0.677281 0.616199 0.322147 0.030 Uiso 1 1 calc R . . . .
C36 C 0.7578(3) 0.7781(3) 0.3934(2) 0.0246(7) Uani 1 1 d . . . . .
H36 H 0.738059 0.816468 0.343411 0.033 Uiso 1 1 calc R . . . .
C37 C 0.8229(4) 0.8417(3) 0.4801(3) 0.0272(7) Uani 1 1 d . . . . .
H37 H 0.846682 0.923316 0.489068 0.036 Uiso 1 1 calc R . . . .
C38 C 0.8520(3) 0.7859(3) 0.5516(2) 0.0261(7) Uani 1 1 d . . . . .
H38 H 0.896124 0.829101 0.610211 0.035 Uiso 1 1 calc R . . . .
C39 C 0.8175(3) 0.6655(2) 0.5392(2) 0.0226(6) Uani 1 1 d . . . . .
H39 H 0.839099 0.627909 0.589324 0.030 Uiso 1 1 calc R . . . .
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'
Br Br -0.2901 2.4595 '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'
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
C14 N1 C1 109.6(2) . . ?
C14 N1 C27 111.4(2) . . ?
C27 N1 C1 110.9(2) . . ?
N1 C1 C2 112.9(2) . . ?
C3 C2 C1 122.4(2) . . ?
C3 C2 C7 116.9(3) . . ?
C7 C2 C1 120.6(3) . . ?
C2 C3 Br1 120.8(2) . . ?
C4 C3 Br1 117.2(2) . . ?
C4 C3 C2 122.0(3) . . ?
C3 C4 C5 119.8(3) . . ?
C4 C5 C6 120.6(3) . . ?
C5 C6 C7 118.1(3) . . ?
C5 C6 C8 120.6(3) . . ?
C7 C6 C8 121.3(3) . . ?
C2 C7 C6 122.5(3) . . ?
C9 C8 C6 120.4(3) . . ?
C13 C8 C6 121.7(3) . . ?
C13 C8 C9 117.8(3) . . ?
C10 C9 C8 120.7(3) . . ?
C11 C10 C9 121.4(3) . . ?
C10 C11 C12 118.6(3) . . ?
C13 C12 C11 120.0(3) . . ?
C12 C13 C8 121.4(3) . . ?
N1 C14 C15 112.1(2) . . ?
C16 C15 C14 124.4(3) . . ?
C16 C15 C20 116.6(3) . . ?
C20 C15 C14 119.0(3) . . ?
C15 C16 Br2 121.3(2) . . ?
C17 C16 Br2 116.8(2) . . ?
C17 C16 C15 121.9(3) . . ?
C18 C17 C16 119.7(3) . . ?
C17 C18 C19 120.8(3) . . ?
C18 C19 C21 120.8(3) . . ?
C20 C19 C18 117.8(3) . . ?
C20 C19 C21 121.3(3) . . ?
C19 C20 C15 123.1(3) . . ?
C22 C21 C19 121.1(3) . . ?
C22 C21 C26 118.0(3) . . ?
C26 C21 C19 120.9(3) . . ?
C23 C22 C21 121.0(3) . . ?
C24 C23 C22 120.3(3) . . ?
C25 C24 C23 119.9(3) . . ?
C24 C25 C26 119.9(3) . . ?
C25 C26 C21 120.9(3) . . ?
N1 C27 C28 110.0(2) . . ?
C29 C28 C27 125.0(3) . . ?
C29 C28 C33 116.7(3) . . ?
C33 C28 C27 118.2(3) . . ?
C28 C29 Br3 121.1(2) . . ?
C30 C29 Br3 117.2(2) . . ?
C30 C29 C28 121.8(3) . . ?
C31 C30 C29 119.8(3) . . ?
C30 C31 C32 120.7(3) . . ?
C31 C32 C34 120.6(3) . . ?
C33 C32 C31 117.9(3) . . ?
C33 C32 C34 121.5(3) . . ?
C32 C33 C28 123.1(3) . . ?
C35 C34 C32 120.8(3) . . ?
C39 C34 C32 121.2(3) . . ?
C39 C34 C35 117.9(3) . . ?
C36 C35 C34 121.0(3) . . ?
C35 C36 C37 119.9(3) . . ?
C38 C37 C36 119.8(3) . . ?
C37 C38 C39 120.6(3) . . ?
C38 C39 C34 120.8(3) . . ?
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
Br1 C3 1.909(3) . ?
Br2 C16 1.907(3) . ?
Br3 C29 1.902(3) . ?
N1 C1 1.478(4) . ?
N1 C14 1.470(4) . ?
N1 C27 1.472(4) . ?
C1 C2 1.506(4) . ?
C2 C3 1.398(4) . ?
C2 C7 1.401(4) . ?
C3 C4 1.383(4) . ?
C4 C5 1.390(4) . ?
C5 C6 1.397(4) . ?
C6 C7 1.405(4) . ?
C6 C8 1.487(4) . ?
C8 C9 1.407(4) . ?
C8 C13 1.395(4) . ?
C9 C10 1.392(4) . ?
C10 C11 1.374(5) . ?
C11 C12 1.414(5) . ?
C12 C13 1.394(4) . ?
C14 C15 1.507(4) . ?
C15 C16 1.402(4) . ?
C15 C20 1.405(4) . ?
C16 C17 1.391(4) . ?
C17 C18 1.389(4) . ?
C18 C19 1.405(4) . ?
C19 C20 1.395(4) . ?
C19 C21 1.486(4) . ?
C21 C22 1.400(5) . ?
C21 C26 1.401(4) . ?
C22 C23 1.391(4) . ?
C23 C24 1.388(5) . ?
C24 C25 1.384(5) . ?
C25 C26 1.401(5) . ?
C27 C28 1.509(4) . ?
C28 C29 1.393(4) . ?
C28 C33 1.406(4) . ?
C29 C30 1.392(4) . ?
C30 C31 1.382(4) . ?
C31 C32 1.404(4) . ?
C32 C33 1.385(4) . ?
C32 C34 1.487(4) . ?
C34 C35 1.405(4) . ?
C34 C39 1.403(4) . ?
C35 C36 1.392(4) . ?
C36 C37 1.403(5) . ?
C37 C38 1.367(5) . ?
C38 C39 1.401(4) . ?
