#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/08/7150859.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_7150859
loop_
_publ_author_name
'Ramachary, Dhevalapally B.'
'Reddy, Y. Vijayendar'
'Prakash, B. Veda'
_publ_section_title
;
 Double cascade reactions based on the Barbas dienamine platform:
 highly stereoselective synthesis of functionalized cyclohexanes for
 cardiovascular agents
;
_journal_issue                   4
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              719
_journal_page_last               726
_journal_paper_doi               10.1039/b718122a
_journal_volume                  6
_journal_year                    2008
_chemical_formula_sum            'C37 H32 N2 O4'
_chemical_formula_weight         568.65
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 105.89(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.027(2)
_cell_length_b                   10.945(2)
_cell_length_c                   24.151(8)
_cell_measurement_temperature    293(2)
_cell_volume                     3057.7(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            28453
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9904
_exptl_absorpt_correction_T_min  0.9670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         5330
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.154
_refine_ls_R_factor_all          0.0897
_refine_ls_R_factor_gt           0.0729
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0590P)²+1.4139P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1515
_refine_ls_wR_factor_ref         0.1602
_reflns_number_gt                4371
_reflns_number_total             5330
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b718122a.txt
_cod_data_source_block           dbr30
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               7150859
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C4 C 0.65093(19) 0.6745(2) 0.62425(11) 0.0417(6) Uani 1 1 d . . .
H4 H 0.6718 0.7365 0.6546 0.050 Uiso 1 1 calc R . .
C5 C 0.76701(19) 0.6309(2) 0.61224(10) 0.0373(5) Uani 1 1 d . . .
C6 C 0.83075(19) 0.7447(2) 0.59707(10) 0.0356(5) Uani 1 1 d . . .
H6 H 0.8386 0.8029 0.6287 0.043 Uiso 1 1 calc R . .
C8 C 0.9520(2) 0.7170(2) 0.59363(10) 0.0379(6) Uani 1 1 d . . .
C9 C 1.0461(2) 0.7546(3) 0.63720(12) 0.0538(7) Uani 1 1 d . . .
H9 H 1.0342 0.7978 0.6682 0.065 Uiso 1 1 calc R . .
C10 C 1.1574(2) 0.7293(3) 0.63558(14) 0.0711(9) Uani 1 1 d . . .
H10 H 1.2195 0.7552 0.6655 0.085 Uiso 1 1 calc R . .
C11 C 1.1774(3) 0.6665(3) 0.59040(16) 0.0713(10) Uani 1 1 d . . .
H11 H 1.2525 0.6486 0.5896 0.086 Uiso 1 1 calc R . .
C12 C 1.0854(3) 0.6303(3) 0.54652(15) 0.0684(9) Uani 1 1 d . . .
H12 H 1.0981 0.5879 0.5155 0.082 Uiso 1 1 calc R . .
C13 C 0.9735(2) 0.6561(3) 0.54765(13) 0.0554(7) Uani 1 1 d . . .
H13 H 0.9120 0.6320 0.5170 0.067 Uiso 1 1 calc R . .
C14 C 1.0393(3) 1.0708(3) 0.57625(13) 0.0613(8) Uani 1 1 d . . .
H14 H 0.9994 0.9998 0.5618 0.074 Uiso 1 1 calc R . .
C15 C 0.9784(2) 1.1763(2) 0.57867(11) 0.0507(7) Uani 1 1 d . . .
C16 C 1.0393(3) 1.2799(3) 0.60009(12) 0.0585(7) Uani 1 1 d . . .
H16 H 0.9998 1.3520 0.6024 0.070 Uiso 1 1 calc R . .
C17 C 1.1581(3) 1.2785(3) 0.61820(14) 0.0666(8) Uani 1 1 d . . .
H17 H 1.1985 1.3495 0.6322 0.080 Uiso 1 1 calc R . .
C18 C 1.2167(3) 1.1727(3) 0.61558(14) 0.0672(8) Uani 1 1 d . . .
H18 H 1.2971 1.1716 0.6280 0.081 Uiso 1 1 calc R . .
C19 C 1.1573(3) 1.0688(3) 0.59479(14) 0.0677(9) Uani 1 1 d . . .
H19 H 1.1971 0.9965 0.5932 0.081 Uiso 1 1 calc R . .
C22 C 0.6872(2) 1.0695(2) 0.56419(12) 0.0554(7) Uani 1 1 d . . .
C23 C 0.8493(3) 1.1810(3) 0.55630(15) 0.0709(9) Uani 1 1 d . . .
H23A H 0.8206 1.2572 0.5676 0.085 Uiso 1 1 calc R . .
H23B H 0.8267 1.1765 0.5146 0.085 Uiso 1 1 calc R . .
C24 C 0.5906(2) 0.5729(2) 0.64700(12) 0.0482(6) Uani 1 1 d . . .
C25 C 0.5218(3) 0.4874(3) 0.61159(16) 0.0732(9) Uani 1 1 d . . .
H25 H 0.5085 0.4939 0.5719 0.088 Uiso 1 1 calc R . .
C26 C 0.4728(3) 0.3931(4) 0.6340(2) 0.0934(12) Uani 1 1 d . . .
H26 H 0.4275 0.3362 0.6092 0.112 Uiso 1 1 calc R . .
C27 C 0.4891(3) 0.3813(4) 0.6913(2) 0.0951(13) Uani 1 1 d . . .
H27 H 0.4555 0.3167 0.7059 0.114 Uiso 1 1 calc R . .
C28 C 0.5557(3) 0.4656(4) 0.72787(18) 0.0870(12) Uani 1 1 d . . .
H28 H 0.5672 0.4587 0.7674 0.104 Uiso 1 1 calc R . .
C29 C 0.6060(3) 0.5614(3) 0.70541(14) 0.0637(8) Uani 1 1 d . . .
H29 H 0.6508 0.6186 0.7303 0.076 Uiso 1 1 calc R . .
C31 C 0.9389(2) 0.5728(3) 0.76339(11) 0.0545(7) Uani 1 1 d . . .
H31A H 0.9154 0.4880 0.7638 0.065 Uiso 1 1 calc R . .
H31B H 0.9243 0.6132 0.7965 0.065 Uiso 1 1 calc R . .
C32 C 1.0657(2) 0.5786(2) 0.76778(10) 0.0476(6) Uani 1 1 d . . .
C33 C 1.1231(3) 0.4836(3) 0.75055(13) 0.0645(8) Uani 1 1 d . . .
H33 H 1.0839 0.4118 0.7368 0.077 Uiso 1 1 calc R . .
C34 C 1.2392(3) 0.4950(4) 0.75367(15) 0.0808(11) Uani 1 1 d . . .
H34 H 1.2777 0.4307 0.7418 0.097 Uiso 1 1 calc R . .
C35 C 1.2980(3) 0.6004(4) 0.77416(15) 0.0826(11) Uani 1 1 d . . .
H35 H 1.3758 0.6082 0.7757 0.099 Uiso 1 1 calc R . .
C36 C 1.2414(3) 0.6932(3) 0.79218(14) 0.0727(9) Uani 1 1 d . . .
H36 H 1.2811 0.7643 0.8066 0.087 Uiso 1 1 calc R . .
C37 C 1.1262(3) 0.6830(3) 0.78925(12) 0.0582(7) Uani 1 1 d . . .
H37 H 1.0887 0.7472 0.8019 0.070 Uiso 1 1 calc R . .
C38 C 0.8416(2) 0.5616(2) 0.66384(10) 0.0382(5) Uani 1 1 d . . .
C39 C 0.5757(2) 0.7384(2) 0.57053(11) 0.0480(6) Uani 1 1 d . . .
H39 H 0.5531 0.6792 0.5396 0.058 Uiso 1 1 calc R . .
H39A H 0.5059 0.7681 0.5787 0.058 Uiso 1 1 calc R . .
C40 C 0.6363(2) 0.8451(2) 0.55045(11) 0.0460(6) Uani 1 1 d . . .
H40 H 0.5882 0.8696 0.5124 0.055 Uiso 1 1 calc R . .
C41 C 0.6479(2) 0.9576(2) 0.59048(11) 0.0476(6) Uani 1 1 d . . .
H41 H 0.7056 0.9392 0.6269 0.057 Uiso 1 1 calc R . .
C42 C 0.7537(2) 0.8060(2) 0.54324(10) 0.0434(6) Uani 1 1 d . . .
H42 H 0.7932 0.8773 0.5341 0.052 Uiso 1 1 calc R . .
H42A H 0.7414 0.7498 0.5111 0.052 Uiso 1 1 calc R . .
C43 C 0.7391(2) 0.5437(2) 0.56348(12) 0.0446(6) Uani 1 1 d . . .
C44 C 0.5375(3) 0.9853(3) 0.60281(14) 0.0645(8) Uani 1 1 d . . .
N3 N 0.4533(3) 1.0050(3) 0.61321(16) 0.1040(11) Uani 1 1 d . . .
N4 N 0.7146(2) 0.4816(2) 0.52427(11) 0.0655(7) Uani 1 1 d . . .
O1 O 0.86987(14) 0.63196(16) 0.71011(7) 0.0446(4) Uani 1 1 d . . .
O3 O 0.62504(19) 1.1386(2) 0.53330(13) 0.1112(11) Uani 1 1 d . . .
O4 O 0.80107(15) 1.07851(16) 0.58001(8) 0.0536(5) Uani 1 1 d . . .
O6 O 0.86953(17) 0.45753(16) 0.66236(8) 0.0597(5) 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'
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
C24 C4 C39 114.4(2) . . ?
C24 C4 C5 112.47(19) . . ?
C39 C4 C5 109.3(2) . . ?
C24 C4 H4 106.8 . . ?
C39 C4 H4 106.8 . . ?
C5 C4 H4 106.8 . . ?
C43 C5 C38 106.5(2) . . ?
C43 C5 C6 110.33(19) . . ?
C38 C5 C6 111.90(18) . . ?
C43 C5 C4 108.76(19) . . ?
C38 C5 C4 110.70(19) . . ?
C6 C5 C4 108.63(18) . . ?
C8 C6 C42 114.19(19) . . ?
C8 C6 C5 113.35(18) . . ?
C42 C6 C5 109.15(19) . . ?
C8 C6 H6 106.5 . . ?
C42 C6 H6 106.5 . . ?
C5 C6 H6 106.5 . . ?
C9 C8 C13 117.6(2) . . ?
C9 C8 C6 120.0(2) . . ?
C13 C8 C6 122.5(2) . . ?
C10 C9 C8 121.2(3) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C10 118.9(3) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 120.8(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C8 C13 C12 120.8(3) . . ?
C8 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C19 C14 C15 121.1(3) . . ?
C19 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C16 C15 C14 118.3(3) . . ?
C16 C15 C23 120.1(3) . . ?
C14 C15 C23 121.6(3) . . ?
C15 C16 C17 120.7(3) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 120.0(3) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 119.9(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C18 C19 C14 119.9(3) . . ?
C18 C19 H19 120.0 . . ?
C14 C19 H19 120.0 . . ?
O3 C22 O4 124.4(3) . . ?
O3 C22 C41 124.7(3) . . ?
O4 C22 C41 110.9(2) . . ?
O4 C23 C15 108.6(2) . . ?
O4 C23 H23A 110.0 . . ?
C15 C23 H23A 110.0 . . ?
O4 C23 H23B 110.0 . . ?
C15 C23 H23B 110.0 . . ?
H23A C23 H23B 108.4 . . ?
C29 C24 C25 117.6(3) . . ?
C29 C24 C4 119.7(3) . . ?
C25 C24 C4 122.7(3) . . ?
C26 C25 C24 121.0(3) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C27 C26 C25 121.3(4) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C26 C27 C28 119.4(3) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 H27 120.3 . . ?
C27 C28 C29 119.6(4) . . ?
C27 C28 H28 120.2 . . ?
C29 C28 H28 120.2 . . ?
C24 C29 C28 121.1(3) . . ?
C24 C29 H29 119.5 . . ?
C28 C29 H29 119.5 . . ?
O1 C31 C32 111.2(2) . . ?
O1 C31 H31A 109.4 . . ?
C32 C31 H31A 109.4 . . ?
O1 C31 H31B 109.4 . . ?
C32 C31 H31B 109.4 . . ?
H31A C31 H31B 108.0 . . ?
C33 C32 C37 119.0(3) . . ?
C33 C32 C31 122.1(3) . . ?
C37 C32 C31 118.9(3) . . ?
C32 C33 C34 119.9(3) . . ?
C32 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C35 C34 C33 120.5(3) . . ?
C35 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C36 C35 C34 119.3(3) . . ?
C36 C35 H35 120.3 . . ?
C34 C35 H35 120.3 . . ?
C35 C36 C37 120.7(3) . . ?
C35 C36 H36 119.7 . . ?
C37 C36 H36 119.7 . . ?
C36 C37 C32 120.6(3) . . ?
C36 C37 H37 119.7 . . ?
C32 C37 H37 119.7 . . ?
O6 C38 O1 125.0(2) . . ?
O6 C38 C5 124.0(2) . . ?
O1 C38 C5 111.0(2) . . ?
C40 C39 C4 113.3(2) . . ?
C40 C39 H39 108.9 . . ?
C4 C39 H39 108.9 . . ?
C40 C39 H39A 108.9 . . ?
C4 C39 H39A 108.9 . . ?
H39 C39 H39A 107.7 . . ?
C39 C40 C42 111.0(2) . . ?
C39 C40 C41 112.3(2) . . ?
C42 C40 C41 111.4(2) . . ?
C39 C40 H40 107.3 . . ?
C42 C40 H40 107.3 . . ?
C41 C40 H40 107.3 . . ?
C44 C41 C22 108.8(2) . . ?
C44 C41 C40 111.0(2) . . ?
C22 C41 C40 111.5(2) . . ?
C44 C41 H41 108.5 . . ?
C22 C41 H41 108.5 . . ?
C40 C41 H41 108.5 . . ?
C40 C42 C6 112.9(2) . . ?
C40 C42 H42 109.0 . . ?
C6 C42 H42 109.0 . . ?
C40 C42 H42A 109.0 . . ?
C6 C42 H42A 109.0 . . ?
H42 C42 H42A 107.8 . . ?
N4 C43 C5 176.4(3) . . ?
N3 C44 C41 178.6(4) . . ?
C38 O1 C31 115.7(2) . . ?
C22 O4 C23 116.0(2) . . ?
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
C4 C24 1.511(3) . ?
C4 C39 1.532(3) . ?
C4 C5 1.575(3) . ?
C4 H4 0.9800 . ?
C5 C43 1.481(4) . ?
C5 C38 1.524(3) . ?
C5 C6 1.558(3) . ?
C6 C8 1.514(3) . ?
C6 C42 1.529(3) . ?
C6 H6 0.9800 . ?
C8 C9 1.380(4) . ?
C8 C13 1.379(3) . ?
C9 C10 1.378(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.366(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.365(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C19 1.366(4) . ?
C14 C15 1.377(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(4) . ?
C15 C23 1.499(4) . ?
C16 C17 1.375(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.366(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.364(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C22 O3 1.176(3) . ?
C22 O4 1.321(3) . ?
C22 C41 1.513(4) . ?
C23 O4 1.451(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C29 1.377(4) . ?
C24 C25 1.380(4) . ?
C25 C26 1.371(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.350(6) . ?
C26 H26 0.9300 . ?
C27 C28 1.373(6) . ?
C27 H27 0.9300 . ?
C28 C29 1.393(5) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C31 O1 1.476(3) . ?
C31 C32 1.501(4) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.373(4) . ?
C32 C37 1.378(4) . ?
C33 C34 1.384(5) . ?
C33 H33 0.9300 . ?
C34 C35 1.373(5) . ?
C34 H34 0.9300 . ?
C35 C36 1.359(5) . ?
C35 H35 0.9300 . ?
C36 C37 1.372(4) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
C38 O6 1.190(3) . ?
C38 O1 1.323(3) . ?
C39 C40 1.525(4) . ?
C39 H39 0.9700 . ?
C39 H39A 0.9700 . ?
C40 C42 1.530(3) . ?
C40 C41 1.548(4) . ?
C40 H40 0.9800 . ?
C41 C44 1.470(4) . ?
C41 H41 0.9800 . ?
C42 H42 0.9700 . ?
C42 H42A 0.9700 . ?
C43 N4 1.137(3) . ?
C44 N3 1.130(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21119047
2 PubChem 139190259
