#------------------------------------------------------------------------------
#$Date: 2021-03-05 03:48:15 +0200 (Fri, 05 Mar 2021) $
#$Revision: 262584 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/20/7242032.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_7242032
loop_
_publ_author_name
'Basak, Tanmoy'
'Frontera, Antonio'
'Chattopadhyay, Shouvik'
_publ_section_title
;
 Insight into non-covalent interactions in two triamine-based mononuclear
 iron(iii) Schiff base complexes with special emphasis on the formation of
 Br⋯π halogen bonding
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              1578
_journal_page_last               1587
_journal_paper_doi               10.1039/D0CE01534B
_journal_volume                  23
_journal_year                    2021
_chemical_compound_source
'slow evaporation of DMF solution of 5; see text'
_chemical_formula_moiety         'C20 H24 Br N O5'
_chemical_formula_sum            'C20 H24 Br N O5'
_chemical_formula_weight         438.31
_chemical_name_systematic
; 
(2aR,7S,7aS,7bR)-7-bromo-7-{[(4aS,5S,6S,8aR)-1,2,3,4,4a,5,6,8a-Octahydro-
6-methylnaphthalene-5-yl]-oxomethyl}-2,2a,3,4,6,7,7a,7b-octahydro-
7b-hydroxy-furo[2,3,4-gh]pyrrolizine-2,6-dione
;
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc6tprf
_audit_creation_method           'SHELXL-93 with manual modification'
_audit_update_record
;
2003-02-07 deposited with the CCDC.	2021-01-05 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.228(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.1266(18)
_cell_length_b                   6.7800(6)
_cell_length_c                   17.9128(15)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      32.98
_cell_measurement_theta_min      30.34
_cell_volume                     979.1(2)
_computing_cell_refinement       'CAD4/PC V1.1 (Kretschmar, 1992)'
_computing_data_collection       'CAD4/PC V1.1 (Kretschmar, 1992)'
_computing_data_reduction
'CAD4 SDP-PLUS (B. A. Frenz & Associates & Enraf-Nonius, 1988)'
_computing_molecular_graphics    'ORTEP-III (Burnett & Johnson, 1996)'
_computing_publication_material
'SHELXL-93 (Sheldrick, 1993) and PARST95 (Nardelli, 1983, 1995)'
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4590
_diffrn_reflns_theta_max         74.93
_diffrn_reflns_theta_min         2.49
_diffrn_standards_decay_%        11.21
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.127
_exptl_absorpt_correction_T_max  0.9962
_exptl_absorpt_correction_T_min  0.5267
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al, 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_description       'elongated plate'
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.839
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.056
_refine_ls_goodness_of_fit_obs   1.016
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         3942
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_restrained_S_obs      1.016
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_obs          0.0440
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0371P)²+0.8111P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1108
_refine_ls_wR_factor_obs         0.0950
_reflns_number_observed          3192
_reflns_number_total             3942
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            d0ce01534b2.cif
_cod_data_source_block           5_DMF
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0371P)^2^+0.8111P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. A new data item '_refine_ls_weighting_details' was
created with the value set to
'w=1/[\s^2^(Fo^2^)+(0.0371P)^2^+0.8111P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7242031--7242032.cif.
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7242032
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
O1 O 0.2104(5) 0.4880(5) 0.5486(2) 0.0565(9) Uani 1 d . .
C2 C 0.3461(7) 0.5820(9) 0.5283(3) 0.0534(12) Uani 1 d . .
C2A C 0.4448(7) 0.6805(7) 0.5939(3) 0.0476(11) Uani 1 d . .
H2A H 0.4322(61) 0.8249(81) 0.5818(28) 0.050(14) Uiso 1 d . .
C3 C 0.6286(7) 0.6198(13) 0.6062(4) 0.0644(14) Uani 1 d . .
H3A H 0.6727(68) 0.5765(112) 0.5653(34) 0.079(20) Uiso 1 d . .
H3B H 0.6869(88) 0.7449(115) 0.6285(39) 0.085(22) Uiso 1 d . .
C4 C 0.6426(7) 0.4529(8) 0.6646(4) 0.0533(13) Uani 1 d . .
H4A H 0.6776(74) 0.3095(100) 0.6450(33) 0.073(18) Uiso 1 d . .
H4B H 0.7107(80) 0.4898(102) 0.7034(38) 0.083(22) Uiso 1 d . .
N5 N 0.4712(4) 0.4237(5) 0.6789(2) 0.0384(8) Uani 1 d . .
C6 C 0.3874(6) 0.2513(6) 0.6769(2) 0.0370(9) Uani 1 d . .
C7 C 0.2033(6) 0.3041(7) 0.6658(3) 0.0401(10) Uani 1 d . .
C7A C 0.2013(6) 0.5079(7) 0.6283(3) 0.0458(11) Uani 1 d . .
H7A1 H 0.0976(62) 0.5990(127) 0.6426(29) 0.076(15) Uiso 1 d . .
C7B C 0.3692(5) 0.5961(7) 0.6595(2) 0.0395(8) Uani 1 d . .
O2X O 0.3721(5) 0.5797(8) 0.4636(2) 0.0746(12) Uani 1 d . .
O6X O 0.4498(4) 0.0879(5) 0.6833(2) 0.0469(7) Uani 1 d . .
C7X C 0.1245(5) 0.3083(7) 0.7403(3) 0.0413(10) Uani 1 d . .
O7Y O 0.0283(4) 0.4396(5) 0.7503(2) 0.0555(9) Uani 1 d . .
Br7Z Br 0.07570(7) 0.10779(8) 0.60418(3) 0.0667(2) Uani 1 d . .
O7BX O 0.3634(5) 0.7178(5) 0.7221(2) 0.0553(9) Uani 1 d . .
H7BX H 0.3974(81) 0.8454(104) 0.7085(38) 0.082(21) Uiso 1 d . .
C1' C 0.1746(5) 0.1478(7) 0.7975(3) 0.0397(10) Uani 1 d . .
H1' H 0.2054(57) 0.0267(72) 0.7733(26) 0.041(14) Uiso 1 d . .
C2' C 0.3248(6) 0.2168(8) 0.8534(3) 0.0476(11) Uani 1 d . .
H2' H 0.4285(79) 0.2204(92) 0.8326(35) 0.079(20) Uiso 1 d . .
C3' C 0.3549(7) 0.0750(10) 0.9178(3) 0.0598(15) Uani 1 d . .
H3' H 0.4749(62) 0.0672(90) 0.9450(28) 0.063(16) Uiso 1 d . .
C4' C 0.2516(7) -0.0653(9) 0.9325(3) 0.0610(14) Uani 1 d . .
H4' H 0.2828(73) -0.1614(92) 0.9746(33) 0.070(17) Uiso 1 d . .
C4A' C 0.0888(7) -0.1038(8) 0.8864(3) 0.0515(12) Uani 1 d . .
H4A' H 0.1082(65) -0.2190(88) 0.8445(31) 0.060(16) Uiso 1 d . .
C5' C -0.0458(9) -0.1742(11) 0.9322(4) 0.066(2) Uani 1 d . .
H5'A H -0.0017(78) -0.2849(99) 0.9620(36) 0.079(20) Uiso 1 d . .
H5'B H -0.0712(78) -0.0659(114) 0.9647(38) 0.083(21) Uiso 1 d . .
C6' C -0.2038(9) -0.2241(11) 0.8821(4) 0.076(2) Uani 1 d . .
H6'A H -0.3005(84) -0.2412(102) 0.9097(37) 0.082(21) Uiso 1 d . .
H6'B H -0.1685(77) -0.3550(131) 0.8504(37) 0.101(24) Uiso 1 d . .
C7' C -0.2618(8) -0.0498(13) 0.8323(5) 0.084(2) Uani 1 d . .
H7'A H -0.2893(78) 0.0601(117) 0.8691(37) 0.093(26) Uiso 1 d . .
H7'B H -0.3680(104) -0.0861(129) 0.7945(46) 0.124(29) Uiso 1 d . .
C8' C -0.1262(7) 0.0217(11) 0.7875(4) 0.066(2) Uani 1 d . .
H8'A H -0.1627(57) 0.1448(90) 0.7515(29) 0.052(14) Uiso 1 d . .
H8'B H -0.1070(72) -0.0927(94) 0.7531(34) 0.068(18) Uiso 1 d . .
C8A' C 0.0311(5) 0.0765(7) 0.8393(3) 0.0440(10) Uani 1 d . .
H8A' H 0.0112(68) 0.2042(82) 0.8730(31) 0.059(16) Uiso 1 d . .
C2'X C 0.3098(9) 0.4275(10) 0.8835(4) 0.065(2) Uani 1 d . .
H2X1 H 0.3191(81) 0.5417(107) 0.8431(40) 0.102(25) Uiso 1 d . .
H2X2 H 0.1948(77) 0.4595(93) 0.8986(33) 0.066(17) Uiso 1 d . .
H2X3 H 0.3833(84) 0.4492(115) 0.9266(40) 0.093(23) Uiso 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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/ol026923b 2002
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 O1 C7A 111.4(4) . . ?
O2X C2 O1 119.8(5) . . ?
O2X C2 C2A 128.4(5) . . ?
O1 C2 C2A 111.8(4) . . ?
C2 C2A C7B 102.2(4) . . ?
C2 C2A C3 114.1(5) . . ?
C7B C2A C3 105.7(4) . . ?
C4 C3 C2A 106.4(4) . . ?
N5 C4 C3 103.2(4) . . ?
C6 N5 C7B 114.8(4) . . ?
C6 N5 C4 126.9(4) . . ?
C7B N5 C4 112.2(4) . . ?
O6X C6 N5 125.6(4) . . ?
O6X C6 C7 128.0(4) . . ?
N5 C6 C7 106.4(4) . . ?
C6 C7 C7A 103.0(4) . . ?
C6 C7 C7X 113.4(4) . . ?
C7A C7 C7X 112.1(4) . . ?
C6 C7 Br7Z 110.9(3) . . ?
C7A C7 Br7Z 113.1(3) . . ?
C7X C7 Br7Z 104.6(3) . . ?
O1 C7A C7B 104.0(4) . . ?
O1 C7A C7 110.4(4) . . ?
C7B C7A C7 103.4(4) . . ?
O7BX C7B N5 111.0(3) . . ?
O7BX C7B C2A 117.4(4) . . ?
N5 C7B C2A 102.5(3) . . ?
O7BX C7B C7A 113.9(4) . . ?
N5 C7B C7A 103.3(4) . . ?
C2A C7B C7A 107.3(4) . . ?
O7Y C7X C1' 123.4(4) . . ?
O7Y C7X C7 119.0(4) . . ?
C1' C7X C7 117.6(4) . . ?
C7X C1' C8A' 113.5(4) . . ?
C7X C1' C2' 110.0(4) . . ?
C8A' C1' C2' 111.3(4) . . ?
C3' C2' C2'X 109.8(5) . . ?
C3' C2' C1' 110.0(4) . . ?
C2'X C2' C1' 114.6(5) . . ?
C4' C3' C2' 124.8(5) . . ?
C3' C4' C4A' 124.0(5) . . ?
C4' C4A' C5' 113.8(5) . . ?
C4' C4A' C8A' 110.8(4) . . ?
C5' C4A' C8A' 110.9(5) . . ?
C6' C5' C4A' 111.4(5) . . ?
C5' C6' C7' 110.6(6) . . ?
C6' C7' C8' 111.5(6) . . ?
C7' C8' C8A' 111.3(6) . . ?
C4A' C8A' C8' 108.5(4) . . ?
C4A' C8A' C1' 108.7(4) . . ?
C8' C8A' C1' 114.1(4) . . ?
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
O1 C2 1.362(6) . ?
O1 C7A 1.445(6) . ?
C2 O2X 1.205(5) . ?
C2 C2A 1.495(7) . ?
C2A C7B 1.505(6) . ?
C2A C3 1.538(8) . ?
C3 C4 1.535(9) . ?
C4 N5 1.461(7) . ?
N5 C6 1.351(6) . ?
N5 C7B 1.450(6) . ?
C6 O6X 1.218(6) . ?
C6 C7 1.527(6) . ?
C7 C7A 1.535(6) . ?
C7 C7X 1.551(7) . ?
C7 Br7Z 1.944(5) . ?
C7A C7B 1.529(6) . ?
C7B O7BX 1.398(5) . ?
C7X O7Y 1.213(5) . ?
C7X C1' 1.516(6) . ?
C1' C8A' 1.540(6) . ?
C1' C2' 1.551(7) . ?
C2' C3' 1.499(8) . ?
C2' C2'X 1.537(8) . ?
C3' C4' 1.317(8) . ?
C4' C4A' 1.491(8) . ?
C4A' C5' 1.524(8) . ?
C4A' C8A' 1.526(7) . ?
C5' C6' 1.510(10) . ?
C6' C7' 1.519(10) . ?
C7' C8' 1.522(9) . ?
C8' C8A' 1.528(7) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O7BX H7BX O6X 0.95(7) 1.77(7) 2.720(5) 177(6) 1_565 yes
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
C7A O1 C2 O2X 180.0(5) . . . . ?
C7A O1 C2 C2A -0.8(6) . . . . ?
O2X C2 C2A C7B -169.2(6) . . . . ?
O1 C2 C2A C7B 11.6(5) . . . . ?
O2X C2 C2A C3 -55.6(8) . . . . ?
O1 C2 C2A C3 125.2(5) . . . . ?
C2 C2A C3 C4 -95.1(6) . . . . ?
C7B C2A C3 C4 16.4(6) . . . . ?
C2A C3 C4 N5 2.4(7) . . . . ?
C3 C4 N5 C6 128.8(5) . . . . ?
C3 C4 N5 C7B -22.1(6) . . . . ?
C7B N5 C6 O6X 171.7(4) . . . . ?
C4 N5 C6 O6X 21.4(8) . . . . ?
C7B N5 C6 C7 -8.7(5) . . . . ?
C4 N5 C6 C7 -159.0(5) . . . . ?
O6X C6 C7 C7A -156.3(5) . . . . ?
N5 C6 C7 C7A 24.2(5) . . . . ?
O6X C6 C7 C7X 82.4(6) . . . . ?
N5 C6 C7 C7X -97.2(4) . . . . ?
O6X C6 C7 Br7Z -35.0(6) . . . . ?
N5 C6 C7 Br7Z 145.5(3) . . . . ?
C2 O1 C7A C7B -10.3(5) . . . . ?
C2 O1 C7A C7 -120.7(4) . . . . ?
C6 C7 C7A O1 81.0(5) . . . . ?
C7X C7 C7A O1 -156.8(4) . . . . ?
Br7Z C7 C7A O1 -38.8(5) . . . . ?
C6 C7 C7A C7B -29.8(4) . . . . ?
C7X C7 C7A C7B 92.4(4) . . . . ?
Br7Z C7 C7A C7B -149.6(3) . . . . ?
C6 N5 C7B O7BX 111.7(4) . . . . ?
C4 N5 C7B O7BX -93.6(5) . . . . ?
C6 N5 C7B C2A -122.1(4) . . . . ?
C4 N5 C7B C2A 32.5(5) . . . . ?
C6 N5 C7B C7A -10.7(5) . . . . ?
C4 N5 C7B C7A 144.0(4) . . . . ?
C2 C2A C7B O7BX -147.1(4) . . . . ?
C3 C2A C7B O7BX 93.3(5) . . . . ?
C2 C2A C7B N5 91.0(4) . . . . ?
C3 C2A C7B N5 -28.6(5) . . . . ?
C2 C2A C7B C7A -17.4(5) . . . . ?
C3 C2A C7B C7A -137.0(5) . . . . ?
O1 C7A C7B O7BX 149.0(4) . . . . ?
C7 C7A C7B O7BX -95.5(4) . . . . ?
O1 C7A C7B N5 -90.5(4) . . . . ?
C7 C7A C7B N5 25.0(4) . . . . ?
O1 C7A C7B C2A 17.4(5) . . . . ?
C7 C7A C7B C2A 132.8(4) . . . . ?
C6 C7 C7X O7Y 138.4(5) . . . . ?
C7A C7 C7X O7Y 22.3(6) . . . . ?
Br7Z C7 C7X O7Y -100.6(4) . . . . ?
C6 C7 C7X C1' -40.8(5) . . . . ?
C7A C7 C7X C1' -156.9(4) . . . . ?
Br7Z C7 C7X C1' 80.2(4) . . . . ?
O7Y C7X C1' C8A' 38.1(6) . . . . ?
C7 C7X C1' C8A' -142.8(4) . . . . ?
O7Y C7X C1' C2' -87.4(5) . . . . ?
C7 C7X C1' C2' 91.7(5) . . . . ?
C7X C1' C2' C3' 169.7(4) . . . . ?
C8A' C1' C2' C3' 43.0(5) . . . . ?
C7X C1' C2' C2'X 45.4(6) . . . . ?
C8A' C1' C2' C2'X -81.3(6) . . . . ?
C2'X C2' C3' C4' 115.1(7) . . . . ?
C1' C2' C3' C4' -12.0(8) . . . . ?
C2' C3' C4' C4A' 0.3(10) . . . . ?
C3' C4' C4A' C5' -145.7(6) . . . . ?
C3' C4' C4A' C8A' -19.8(8) . . . . ?
C4' C4A' C5' C6' -176.0(6) . . . . ?
C8A' C4A' C5' C6' 58.1(7) . . . . ?
C4A' C5' C6' C7' -55.2(9) . . . . ?
C5' C6' C7' C8' 54.6(10) . . . . ?
C6' C7' C8' C8A' -56.9(9) . . . . ?
C4' C4A' C8A' C8' 174.2(5) . . . . ?
C5' C4A' C8A' C8' -58.3(6) . . . . ?
C4' C4A' C8A' C1' 49.6(6) . . . . ?
C5' C4A' C8A' C1' 177.1(5) . . . . ?
C7' C8' C8A' C4A' 57.9(7) . . . . ?
C7' C8' C8A' C1' 179.2(6) . . . . ?
C7X C1' C8A' C4A' 171.8(4) . . . . ?
C2' C1' C8A' C4A' -63.4(5) . . . . ?
C7X C1' C8A' C8' 50.6(6) . . . . ?
C2' C1' C8A' C8' 175.4(5) . . . . ?
