#------------------------------------------------------------------------------
#$Date: 2025-04-22 19:48:50 +0300 (Tue, 22 Apr 2025) $
#$Revision: 299347 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/48/8104818.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_8104818
loop_
_publ_author_name
'Li, Tianyu'
'Xu, Xindi'
'Wang, Man'
'Wang, Xia'
'Wu, Qiong'
_publ_section_title
;
 Crystal structure of N,N′-bis(4-bromosalicylidene)
 ethylene-1,2-diaminopropan, C34H32Br4N4O4
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              319
_journal_page_last               321
_journal_paper_doi               10.1515/ncrs-2020-0546
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C17 H16 Br2 N2 O2'
_chemical_formula_sum            'C17 H16 Br2 N2 O2'
_chemical_formula_weight         440.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 92.7260(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.3126(5)
_cell_length_b                   6.9654(2)
_cell_length_c                   29.3000(10)
_cell_measurement_reflns_used    7377
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.93
_cell_measurement_theta_min      3.18
_cell_volume                     3325.41(18)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            54956
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.428
_diffrn_reflns_theta_min         2.382
_exptl_absorpt_coefficient_mu    4.886
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0091
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0988 before and 0.0655 after correction.
The Ratio of minimum to maximum transmission is 0.3297.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_density_meas      .
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         6827
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0349
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0260P)²+2.4493P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0799
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4981
_reflns_number_total             6827
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0546_suppl.cif
_cod_data_source_block           sk12
_cod_depositor_comments
;

2025-04-22
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C34 H32 Br4 N4 O4'
_cod_original_formula_weight         880.27
_cod_original_formula_moiety         '2(C17 H16 Br2 N2 O2)'
_cod_original_formula_units_Z            4
_cod_database_code               8104818
_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.
;
_shelx_estimated_absorpt_t_max   0.473
_shelx_estimated_absorpt_t_min   0.413
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C7(H7), C11(H11), C14(H14), C16(H16), C17(H17),
 C20(H20), C22(H22), C23(H23), C24(H24), C28(H28), C30(H30), C31(H31), C33(H33)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C27(H27A,H27B,H27C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3A), O4(H4)
;
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'
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 0.49023(3) 0.17925(6) 0.54696(2) 0.05009(11) Uani 1 1 d . . . . .
Br2 Br 0.30537(3) 0.18836(6) 0.98393(2) 0.05271(12) Uani 1 1 d . . . . .
Br3 Br 0.67421(3) -0.39478(6) 0.54938(2) 0.04996(11) Uani 1 1 d . . . . .
Br4 Br 0.56008(3) 1.34275(6) 0.96431(2) 0.05096(11) Uani 1 1 d . . . . .
O1 O 0.38663(17) 0.4417(4) 0.69950(9) 0.0481(7) Uani 1 1 d . . . . .
H1 H 0.3705 0.5415 0.7124 0.072 Uiso 1 1 calc GR . . . .
O2 O 0.38264(16) 0.4751(4) 0.82863(9) 0.0461(6) Uani 1 1 d . . . . .
H2 H 0.3810 0.5758 0.8129 0.069 Uiso 1 1 calc GR . . . .
O3 O 0.55090(16) -0.0257(4) 0.68329(9) 0.0480(7) Uani 1 1 d . . . . .
H3A H 0.5581 0.0708 0.7002 0.072 Uiso 1 1 calc GR . . . .
O4 O 0.66154(17) 0.9754(4) 0.82433(9) 0.0496(7) Uani 1 1 d . . . . .
H4 H 0.6609 0.8678 0.8113 0.074 Uiso 1 1 calc GR . . . .
N1 N 0.33810(18) 0.7944(4) 0.70670(11) 0.0427(7) Uani 1 1 d . . . . .
N2 N 0.34572(18) 0.8243(4) 0.80694(11) 0.0417(7) Uani 1 1 d . . . . .
N3 N 0.5991(2) 0.3182(4) 0.70434(11) 0.0505(8) Uani 1 1 d . . . . .
N4 N 0.6158(2) 0.6304(4) 0.80629(12) 0.0515(9) Uani 1 1 d . . . . .
C1 C 0.3851(2) 0.6649(5) 0.63712(13) 0.0397(8) Uani 1 1 d . . . . .
C2 C 0.4000(2) 0.6964(5) 0.59127(13) 0.0426(9) Uani 1 1 d . . . . .
H2A H 0.3882 0.8192 0.5785 0.051 Uiso 1 1 calc R . . . .
C3 C 0.4313(2) 0.5558(5) 0.56369(13) 0.0430(9) Uani 1 1 d . . . . .
H3 H 0.4412 0.5798 0.5325 0.052 Uiso 1 1 calc R . . . .
C4 C 0.4476(2) 0.3776(5) 0.58351(13) 0.0411(8) Uani 1 1 d . . . . .
C5 C 0.4330(2) 0.3390(5) 0.62862(13) 0.0420(9) Uani 1 1 d . . . . .
H5 H 0.4446 0.2154 0.6410 0.050 Uiso 1 1 calc R . . . .
C6 C 0.4012(2) 0.4813(5) 0.65578(13) 0.0412(9) Uani 1 1 d . . . . .
C7 C 0.3533(2) 0.8190(5) 0.66507(13) 0.0410(8) Uani 1 1 d . . . . .
H7 H 0.3436 0.9416 0.6516 0.049 Uiso 1 1 calc R . . . .
C8 C 0.3043(2) 0.9554(5) 0.73195(14) 0.0464(9) Uani 1 1 d . . . . .
H8A H 0.2461 0.9281 0.7377 0.056 Uiso 1 1 calc R . . . .
H8B H 0.3059 1.0726 0.7129 0.056 Uiso 1 1 calc R . . . .
C9 C 0.3507(2) 0.9931(5) 0.77727(13) 0.0442(9) Uani 1 1 d . . . . .
H9 H 0.3240 1.1036 0.7925 0.053 Uiso 1 1 calc R . . . .
C10 C 0.4405(2) 1.0422(6) 0.77204(14) 0.0471(9) Uani 1 1 d . . . . .
H10A H 0.4660 1.0755 0.8020 0.071 Uiso 1 1 calc GR . . . .
H10B H 0.4447 1.1516 0.7512 0.071 Uiso 1 1 calc GR . . . .
H10C H 0.4688 0.9312 0.7596 0.071 Uiso 1 1 calc GR . . . .
C11 C 0.3090(2) 0.8404(5) 0.84424(13) 0.0404(8) Uani 1 1 d . . . . .
H11 H 0.2839 0.9590 0.8513 0.049 Uiso 1 1 calc R . . . .
C12 C 0.3048(2) 0.6817(5) 0.87620(12) 0.0380(8) Uani 1 1 d . . . . .
C13 C 0.3435(2) 0.5047(5) 0.86773(12) 0.0373(8) Uani 1 1 d . . . . .
C14 C 0.3437(2) 0.3583(5) 0.89989(13) 0.0409(8) Uani 1 1 d . . . . .
H14 H 0.3708 0.2403 0.8946 0.049 Uiso 1 1 calc R . . . .
C15 C 0.3037(2) 0.3874(5) 0.93963(13) 0.0405(8) Uani 1 1 d . . . . .
C16 C 0.2627(2) 0.5566(5) 0.94857(13) 0.0440(9) Uani 1 1 d . . . . .
H16 H 0.2342 0.5716 0.9759 0.053 Uiso 1 1 calc R . . . .
C17 C 0.2642(2) 0.7019(5) 0.91699(12) 0.0413(8) Uani 1 1 d . . . . .
H17 H 0.2371 0.8193 0.9230 0.050 Uiso 1 1 calc R . . . .
C18 C 0.6529(2) 0.1436(5) 0.64246(12) 0.0374(8) Uani 1 1 d . . . . .
C19 C 0.6045(2) -0.0203(5) 0.64938(12) 0.0390(8) Uani 1 1 d . . . . .
C20 C 0.6103(2) -0.1807(5) 0.62189(12) 0.0389(8) Uani 1 1 d . . . . .
H20 H 0.5771 -0.2905 0.6263 0.047 Uiso 1 1 calc R . . . .
C21 C 0.6659(2) -0.1768(5) 0.58780(12) 0.0402(8) Uani 1 1 d . . . . .
C22 C 0.7163(2) -0.0200(5) 0.58040(13) 0.0416(9) Uani 1 1 d . . . . .
H22 H 0.7548 -0.0222 0.5571 0.050 Uiso 1 1 calc R . . . .
C23 C 0.7088(2) 0.1387(5) 0.60798(12) 0.0404(8) Uani 1 1 d . . . . .
H23 H 0.7425 0.2474 0.6034 0.049 Uiso 1 1 calc R . . . .
C24 C 0.6470(2) 0.3134(5) 0.67095(13) 0.0422(8) Uani 1 1 d . . . . .
H24 H 0.6793 0.4230 0.6647 0.051 Uiso 1 1 calc R . . . .
C25 C 0.5962(3) 0.4946(6) 0.73169(15) 0.0598(12) Uani 1 1 d . . . . .
H25A H 0.5395 0.5461 0.7305 0.072 Uiso 1 1 calc R . . . .
H25B H 0.6326 0.5929 0.7190 0.072 Uiso 1 1 calc R . . . .
C26 C 0.6234(3) 0.4514(6) 0.78026(15) 0.0548(11) Uani 1 1 d . . . . .
H26 H 0.5879 0.3493 0.7930 0.066 Uiso 1 1 calc R . . . .
C27 C 0.7134(2) 0.3862(6) 0.78234(14) 0.0487(10) Uani 1 1 d . . . . .
H27A H 0.7475 0.4867 0.7695 0.073 Uiso 1 1 calc GR . . . .
H27B H 0.7186 0.2679 0.7646 0.073 Uiso 1 1 calc GR . . . .
H27C H 0.7316 0.3626 0.8142 0.073 Uiso 1 1 calc GR . . . .
C28 C 0.5708(2) 0.6361(5) 0.84066(13) 0.0436(9) Uani 1 1 d . . . . .
H28 H 0.5396 0.5259 0.8479 0.052 Uiso 1 1 calc R . . . .
C29 C 0.5657(2) 0.8065(5) 0.86897(12) 0.0391(8) Uani 1 1 d . . . . .
C30 C 0.5149(2) 0.8111(5) 0.90613(12) 0.0399(8) Uani 1 1 d . . . . .
H30 H 0.4823 0.7019 0.9124 0.048 Uiso 1 1 calc R . . . .
C31 C 0.5109(2) 0.9711(5) 0.93397(13) 0.0431(9) Uani 1 1 d . . . . .
H31 H 0.4750 0.9742 0.9586 0.052 Uiso 1 1 calc R . . . .
C32 C 0.5604(2) 1.1263(5) 0.92502(13) 0.0401(8) Uani 1 1 d . . . . .
C33 C 0.6112(2) 1.1299(5) 0.88855(12) 0.0380(8) Uani 1 1 d . . . . .
H33 H 0.6441 1.2392 0.8830 0.046 Uiso 1 1 calc R . . . .
C34 C 0.6131(2) 0.9699(5) 0.86004(12) 0.0374(8) 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 0.0033 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'
O O 0.0106 0.0060 '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
C7 N1 C8 118.5(3) . .
C11 N2 C9 118.6(3) . .
C24 N3 C25 118.3(3) . .
C28 N4 C26 120.1(3) . .
C2 C1 C6 118.6(3) . .
C2 C1 C7 120.5(3) . .
C6 C1 C7 120.9(3) . .
C3 C2 C1 122.5(3) . .
C2 C3 C4 117.2(4) . .
C3 C4 Br1 118.8(3) . .
C5 C4 Br1 118.8(3) . .
C5 C4 C3 122.4(4) . .
C4 C5 C6 119.8(3) . .
O1 C6 C1 121.2(3) . .
O1 C6 C5 119.3(3) . .
C5 C6 C1 119.6(3) . .
N1 C7 C1 122.1(3) . .
N1 C8 C9 112.9(3) . .
N2 C9 C8 109.9(3) . .
N2 C9 C10 108.7(3) . .
C8 C9 C10 113.2(3) . .
N2 C11 C12 121.6(3) . .
C13 C12 C11 121.0(3) . .
C17 C12 C11 120.9(3) . .
C17 C12 C13 118.1(3) . .
O2 C13 C12 121.0(3) . .
O2 C13 C14 118.5(3) . .
C14 C13 C12 120.5(3) . .
C15 C14 C13 118.7(3) . .
C14 C15 Br2 118.6(3) . .
C14 C15 C16 122.5(3) . .
C16 C15 Br2 118.9(3) . .
C17 C16 C15 118.3(3) . .
C16 C17 C12 121.7(4) . .
C19 C18 C24 121.6(3) . .
C23 C18 C19 118.4(3) . .
C23 C18 C24 120.0(3) . .
O3 C19 C18 120.9(3) . .
O3 C19 C20 118.0(3) . .
C20 C19 C18 121.1(3) . .
C21 C20 C19 118.1(3) . .
C20 C21 Br3 118.7(3) . .
C20 C21 C22 122.8(3) . .
C22 C21 Br3 118.4(3) . .
C23 C22 C21 117.9(3) . .
C22 C23 C18 121.7(3) . .
N3 C24 C18 121.2(3) . .
N3 C25 C26 109.5(4) . .
N4 C26 C25 107.1(3) . .
N4 C26 C27 109.5(3) . .
C25 C26 C27 109.6(4) . .
N4 C28 C29 121.8(3) . .
C30 C29 C28 121.0(3) . .
C30 C29 C34 118.5(3) . .
C34 C29 C28 120.5(3) . .
C31 C30 C29 121.5(3) . .
C32 C31 C30 118.2(3) . .
C31 C32 Br4 119.2(3) . .
C31 C32 C33 122.5(3) . .
C33 C32 Br4 118.3(3) . .
C32 C33 C34 118.7(3) . .
O4 C34 C29 121.1(3) . .
O4 C34 C33 118.4(3) . .
C33 C34 C29 120.4(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C4 1.900(4) .
Br2 C15 1.898(4) .
Br3 C21 1.899(3) .
Br4 C32 1.897(4) .
O1 C6 1.343(4) .
O2 C13 1.353(4) .
O3 C19 1.355(4) .
O4 C34 1.341(4) .
N1 C7 1.268(5) .
N1 C8 1.466(5) .
N2 C9 1.467(5) .
N2 C11 1.276(5) .
N3 C24 1.282(5) .
N3 C25 1.469(5) .
N4 C26 1.470(5) .
N4 C28 1.275(5) .
C1 C2 1.394(5) .
C1 C6 1.410(5) .
C1 C7 1.461(5) .
C2 C3 1.382(5) .
C3 C4 1.390(5) .
C4 C5 1.381(5) .
C5 C6 1.386(5) .
C8 C9 1.520(5) .
C9 C10 1.520(5) .
C11 C12 1.452(5) .
C12 C13 1.413(5) .
C12 C17 1.400(5) .
C13 C14 1.389(5) .
C14 C15 1.376(5) .
C15 C16 1.386(5) .
C16 C17 1.373(5) .
C18 C19 1.408(5) .
C18 C23 1.393(5) .
C18 C24 1.454(5) .
C19 C20 1.384(5) .
C20 C21 1.380(5) .
C21 C22 1.391(5) .
C22 C23 1.378(5) .
C25 C26 1.501(6) .
C26 C27 1.535(6) .
C28 C29 1.453(5) .
C29 C30 1.400(5) .
C29 C34 1.408(5) .
C30 C31 1.385(5) .
C31 C32 1.383(5) .
C32 C33 1.383(5) .
C33 C34 1.394(5) .
