#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/32/1503233.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_1503233
loop_
_publ_author_name
'Escudero-Adán, Eduardo C'
'Martínez Belmonte, Marta'
'Benet-Buchholz, Jordi'
'Kleij, Arjan W.'
_publ_section_title
;
 Practical approach to structurally diverse monoimine salts and
 nonsymmetrical metallosalphen complexes.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              4592
_journal_page_last               4595
_journal_paper_doi               10.1021/ol101898y
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C29 H45 Br2 N3 O'
_chemical_formula_weight         611.50
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.8418(10)
_cell_length_b                   14.3022(7)
_cell_length_c                   13.0883(6)
_cell_measurement_reflns_used    2589
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.61
_cell_measurement_theta_min      2.47
_cell_volume                     2965.5(3)
_computing_cell_refinement       'Bruker APEX2 v2009.1-0'
_computing_data_collection       'Bruker APEX2 v2009.1-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Kappa 4-axis goniometer bruker-nonius'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support
'magnetic support whith 10 micron nylon fiber cryoloop'
_diffrn_radiation_monochromator  'Multilayer Montel 200 mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_sigmaI/netI    0.1224
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14617
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         34.59
_diffrn_reflns_theta_min         1.92
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_source_current           70
_diffrn_source_power             50
_diffrn_source_size              '3 mm x 0.3 mm fine focus'
_diffrn_source_type              'Bruker-Nonius FR 591'
_exptl_absorpt_coefficient_mu    2.759
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.820
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.114
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.017(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         10653
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0604
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0527P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1428
_refine_ls_wR_factor_ref         0.1621
_reflns_number_gt                6848
_reflns_number_total             10653
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101898y_si_003.cif
_cod_data_source_block           ak722
_cod_depositor_comments
;
The following automatic conversions were performed:
'_diffrn_measurement_specimen_suppport' tag replaced with
'_diffrn_measurement_specimen_support'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      Pna2(1)
_cod_database_code               1503233
loop_
_symmetry_equiv_pos_as_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'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.61371(3) 1.37209(3) 0.12873(4) 0.03320(12) Uani 1 1 d .
Br2 Br 0.49467(3) 0.62049(3) -0.12958(4) 0.03848(13) Uani 1 1 d .
C1 C 0.5925(2) 1.2414(3) 0.1121(3) 0.0257(8) Uani 1 1 d .
C2 C 0.5412(2) 1.2143(3) 0.0324(3) 0.0226(8) Uani 1 1 d .
H2 H 0.5171 1.2594 -0.0122 0.027 Uiso 1 1 calc R
C3 C 0.5253(3) 1.1178(3) 0.0181(3) 0.0219(8) Uani 1 1 d .
C4 C 0.5639(2) 1.0526(3) 0.0829(3) 0.0213(7) Uani 1 1 d .
C5 C 0.6162(3) 1.0843(3) 0.1605(3) 0.0252(8) Uani 1 1 d .
H5 H 0.6435 1.0399 0.2033 0.030 Uiso 1 1 calc R
C6 C 0.6302(3) 1.1801(3) 0.1780(3) 0.0288(9) Uani 1 1 d .
H6 H 0.6643 1.2013 0.2330 0.035 Uiso 1 1 calc R
C7 C 0.5500(2) 0.8975(2) 0.1329(3) 0.0193(7) Uani 1 1 d .
H7 H 0.5585 0.9195 0.2005 0.023 Uiso 1 1 calc R
C8 C 0.5380(2) 0.7983(2) 0.1177(3) 0.0179(6) Uani 1 1 d .
C9 C 0.5274(3) 0.7611(3) 0.0184(3) 0.0221(8) Uani 1 1 d .
H9 H 0.5304 0.8013 -0.0392 0.027 Uiso 1 1 calc R
C10 C 0.5130(3) 0.6676(3) 0.0046(3) 0.0236(8) Uani 1 1 d .
C11 C 0.5075(3) 0.6069(3) 0.0885(3) 0.0235(8) Uani 1 1 d .
H11 H 0.4970 0.5422 0.0782 0.028 Uiso 1 1 calc R
C12 C 0.5174(2) 0.6414(3) 0.1853(3) 0.0196(7) Uani 1 1 d .
H12 H 0.5140 0.5992 0.2412 0.023 Uiso 1 1 calc R
C13 C 0.5326(2) 0.7377(3) 0.2060(3) 0.0179(7) Uani 1 1 d .
N1 N 0.4706(2) 1.0872(3) -0.0575(3) 0.0269(7) Uani 1 1 d .
H1A H 0.4603 1.0271 -0.0647 0.032 Uiso 1 1 calc R
H1B H 0.4463 1.1279 -0.0984 0.032 Uiso 1 1 calc R
N2 N 0.5499(2) 0.9568(2) 0.0605(3) 0.0231(7) Uani 1 1 d .
O1 O 0.54222(18) 0.7686(2) 0.2972(2) 0.0239(6) Uani 1 1 d .
C1A C 0.8217(2) 0.7532(3) 0.3156(3) 0.0189(7) Uani 1 1 d .
H1A1 H 0.8644 0.7733 0.2649 0.023 Uiso 1 1 calc R
H1A2 H 0.8524 0.7371 0.3792 0.023 Uiso 1 1 calc R
C2A C 0.7645(3) 0.8359(3) 0.3381(3) 0.0268(8) Uani 1 1 d .
H2A1 H 0.7267 0.8474 0.2792 0.032 Uiso 1 1 calc R
H2A2 H 0.7291 0.8223 0.3987 0.032 Uiso 1 1 calc R
C3A C 0.8183(3) 0.9215(3) 0.3580(3) 0.0291(9) Uani 1 1 d .
H3A1 H 0.8640 0.9046 0.4062 0.035 Uiso 1 1 calc R
H3A2 H 0.8449 0.9413 0.2931 0.035 Uiso 1 1 calc R
C4A C 0.7696(3) 1.0020(3) 0.4012(4) 0.0400(11) Uani 1 1 d .
H4A1 H 0.7262 1.0214 0.3524 0.060 Uiso 1 1 calc R
H4A2 H 0.8081 1.0544 0.4142 0.060 Uiso 1 1 calc R
H4A3 H 0.7428 0.9830 0.4654 0.060 Uiso 1 1 calc R
C5A C 0.8456(2) 0.5893(3) 0.2780(3) 0.0186(7) Uani 1 1 d .
H5A1 H 0.8654 0.5820 0.3492 0.022 Uiso 1 1 calc R
H5A2 H 0.8944 0.6102 0.2366 0.022 Uiso 1 1 calc R
C6A C 0.8177(3) 0.4931(3) 0.2387(3) 0.0239(8) Uani 1 1 d .
H6A1 H 0.7655 0.4733 0.2742 0.029 Uiso 1 1 calc R
H6A2 H 0.8056 0.4966 0.1646 0.029 Uiso 1 1 calc R
C7A C 0.8876(3) 0.4221(3) 0.2581(4) 0.0278(9) Uani 1 1 d .
H7A1 H 0.9402 0.4434 0.2244 0.033 Uiso 1 1 calc R
H7A2 H 0.8986 0.4180 0.3325 0.033 Uiso 1 1 calc R
C8A C 0.8640(4) 0.3267(3) 0.2181(4) 0.0397(12) Uani 1 1 d .
H8A1 H 0.8122 0.3054 0.2516 0.059 Uiso 1 1 calc R
H8A2 H 0.9098 0.2825 0.2325 0.059 Uiso 1 1 calc R
H8A3 H 0.8548 0.3303 0.1441 0.059 Uiso 1 1 calc R
C9A C 0.7040(2) 0.6403(3) 0.3414(3) 0.0205(7) Uani 1 1 d .
H9A1 H 0.6762 0.5848 0.3110 0.025 Uiso 1 1 calc R
H9A2 H 0.6632 0.6926 0.3385 0.025 Uiso 1 1 calc R
C10A C 0.7231(2) 0.6192(3) 0.4530(3) 0.0208(7) Uani 1 1 d .
H10A H 0.7567 0.5610 0.4581 0.025 Uiso 1 1 calc R
H10B H 0.7566 0.6709 0.4828 0.025 Uiso 1 1 calc R
C11A C 0.6411(3) 0.6082(4) 0.5117(3) 0.0290(9) Uani 1 1 d .
H11A H 0.6090 0.6674 0.5073 0.035 Uiso 1 1 calc R
H11B H 0.6068 0.5589 0.4785 0.035 Uiso 1 1 calc R
C12A C 0.6524(3) 0.5832(3) 0.6227(4) 0.0286(8) Uani 1 1 d .
H12A H 0.6816 0.5231 0.6280 0.043 Uiso 1 1 calc R
H12B H 0.5969 0.5786 0.6556 0.043 Uiso 1 1 calc R
H12C H 0.6859 0.6318 0.6566 0.043 Uiso 1 1 calc R
C13A C 0.7466(2) 0.6813(3) 0.1681(3) 0.0201(7) Uani 1 1 d .
H13A H 0.7096 0.7370 0.1687 0.024 Uiso 1 1 calc R
H13B H 0.7113 0.6270 0.1487 0.024 Uiso 1 1 calc R
C14A C 0.8137(3) 0.6951(3) 0.0861(3) 0.0240(8) Uani 1 1 d .
H14A H 0.8384 0.6338 0.0677 0.029 Uiso 1 1 calc R
H14B H 0.8596 0.7350 0.1135 0.029 Uiso 1 1 calc R
C15A C 0.7761(3) 0.7412(3) -0.0100(3) 0.0270(9) Uani 1 1 d .
H15A H 0.8147 0.7306 -0.0683 0.032 Uiso 1 1 calc R
H15B H 0.7216 0.7107 -0.0263 0.032 Uiso 1 1 calc R
C16A C 0.7619(3) 0.8450(3) 0.0024(4) 0.0347(10) Uani 1 1 d .
H16A H 0.7285 0.8564 0.0642 0.052 Uiso 1 1 calc R
H16B H 0.7314 0.8690 -0.0573 0.052 Uiso 1 1 calc R
H16C H 0.8164 0.8768 0.0082 0.052 Uiso 1 1 calc R
N1A N 0.77966(19) 0.6655(2) 0.2760(2) 0.0174(6) 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'
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'
Br Br -0.2901 2.4595 '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
C6 C1 C2 123.7(4)
C6 C1 Br1 118.5(3)
C2 C1 Br1 117.7(3)
C1 C2 C3 118.7(4)
N1 C3 C4 119.6(4)
N1 C3 C2 120.9(4)
C4 C3 C2 119.4(4)
C5 C4 C3 119.1(4)
C5 C4 N2 124.1(4)
C3 C4 N2 116.7(4)
C4 C5 C6 122.1(4)
C1 C6 C5 116.9(4)
N2 C7 C8 123.5(4)
C9 C8 C7 120.8(4)
C9 C8 C13 120.1(3)
C7 C8 C13 119.1(4)
C10 C9 C8 120.6(4)
C9 C10 C11 120.7(4)
C9 C10 Br2 119.6(3)
C11 C10 Br2 119.6(3)
C12 C11 C10 119.7(4)
C11 C12 C13 122.9(4)
O1 C13 C12 122.0(3)
O1 C13 C8 122.0(4)
C12 C13 C8 116.0(4)
C7 N2 C4 119.3(3)
N1A C1A C2A 116.7(3)
C3A C2A C1A 109.1(3)
C4A C3A C2A 113.4(4)
N1A C5A C6A 116.3(3)
C7A C6A C5A 109.4(3)
C8A C7A C6A 111.3(4)
N1A C9A C10A 115.6(3)
C11A C10A C9A 109.6(3)
C12A C11A C10A 114.3(4)
N1A C13A C14A 115.6(3)
C13A C14A C15A 111.1(3)
C16A C15A C14A 113.0(4)
C5A N1A C1A 106.7(3)
C5A N1A C9A 111.4(3)
C1A N1A C9A 110.6(3)
C5A N1A C13A 111.2(3)
C1A N1A C13A 110.3(3)
C9A N1A C13A 106.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.912(4)
Br2 C10 1.903(4)
C1 C6 1.367(6)
C1 C2 1.377(6)
C2 C3 1.414(6)
C3 N1 1.386(6)
C3 C4 1.402(6)
C4 C5 1.387(6)
C4 N2 1.419(5)
C5 C6 1.407(7)
C7 N2 1.272(5)
C7 C8 1.444(5)
C8 C9 1.414(6)
C8 C13 1.447(5)
C9 C10 1.369(6)
C10 C11 1.401(6)
C11 C12 1.369(6)
C12 C13 1.424(6)
C13 O1 1.283(5)
C1A N1A 1.513(5)
C1A C2A 1.519(6)
C2A C3A 1.514(6)
C3A C4A 1.497(6)
C5A N1A 1.509(5)
C5A C6A 1.534(6)
C6A C7A 1.524(6)
C7A C8A 1.508(7)
C9A N1A 1.516(5)
C9A C10A 1.522(5)
C10A C11A 1.518(6)
C11A C12A 1.506(6)
C13A N1A 1.523(5)
C13A C14A 1.523(5)
C14A C15A 1.540(6)
C15A C16A 1.510(6)
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
C6 C1 C2 C3 1.0(6)
Br1 C1 C2 C3 179.4(3)
C1 C2 C3 N1 176.5(4)
C1 C2 C3 C4 -2.0(6)
N1 C3 C4 C5 -177.8(4)
C2 C3 C4 C5 0.7(5)
N1 C3 C4 N2 5.5(5)
C2 C3 C4 N2 -175.9(3)
C3 C4 C5 C6 1.6(6)
N2 C4 C5 C6 178.0(4)
C2 C1 C6 C5 1.2(6)
Br1 C1 C6 C5 -177.2(3)
C4 C5 C6 C1 -2.6(6)
N2 C7 C8 C9 1.7(5)
N2 C7 C8 C13 -175.1(3)
C7 C8 C9 C10 -177.6(3)
C13 C8 C9 C10 -0.8(6)
C8 C9 C10 C11 0.7(6)
C8 C9 C10 Br2 177.6(3)
C9 C10 C11 C12 -0.6(6)
Br2 C10 C11 C12 -177.4(3)
C10 C11 C12 C13 0.6(6)
C11 C12 C13 O1 -179.5(4)
C11 C12 C13 C8 -0.7(5)
C9 C8 C13 O1 179.6(3)
C7 C8 C13 O1 -3.5(5)
C9 C8 C13 C12 0.8(5)
C7 C8 C13 C12 177.6(3)
C8 C7 N2 C4 -178.8(3)
C5 C4 N2 C7 33.4(6)
C3 C4 N2 C7 -150.2(4)
N1A C1A C2A C3A -169.7(3)
C1A C2A C3A C4A -168.5(4)
N1A C5A C6A C7A -173.0(3)
C5A C6A C7A C8A -178.4(4)
N1A C9A C10A C11A 172.4(3)
C9A C10A C11A C12A 177.6(4)
N1A C13A C14A C15A -161.6(3)
C13A C14A C15A C16A 77.0(5)
C6A C5A N1A C1A -178.8(3)
C6A C5A N1A C9A 60.3(4)
C6A C5A N1A C13A -58.5(4)
C2A C1A N1A C5A -169.9(3)
C2A C1A N1A C9A -48.5(4)
C2A C1A N1A C13A 69.2(4)
C10A C9A N1A C5A 57.2(4)
C10A C9A N1A C1A -61.3(4)
C10A C9A N1A C13A 178.7(3)
C14A C13A N1A C5A -50.7(4)
C14A C13A N1A C1A 67.5(4)
C14A C13A N1A C9A -172.3(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139037882
