#------------------------------------------------------------------------------
#$Date: 2019-11-08 03:21:39 +0200 (Fri, 08 Nov 2019) $
#$Revision: 225033 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/69/7156928.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_7156928
loop_
_publ_author_name
'Salam, Abdus'
'Ray, Sayan'
'Zaid, Md Abu'
'Kumar, Dileep'
'Khan, Tabrez'
_publ_section_title
;
 Total syntheses of several iridolactones and the putative structure of
 noriridoid scholarein A: an intramolecular Pauson-Khand reaction based
 one-stop synthetic solution.
;
_journal_issue                   28
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6831
_journal_page_last               6842
_journal_paper_doi               10.1039/c9ob00855a
_journal_volume                  17
_journal_year                    2019
_chemical_formula_sum            'C16 H19 N O5'
_chemical_formula_weight         305.32
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-02-19 deposited with the CCDC.    2019-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                85.482(15)
_cell_angle_beta                 85.127(14)
_cell_angle_gamma                68.851(13)
_cell_formula_units_Z            2
_cell_length_a                   6.691(2)
_cell_length_b                   7.895(3)
_cell_length_c                   15.590(6)
_cell_measurement_reflns_used    25758
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      28.709
_cell_measurement_theta_min      2.626
_cell_volume                     764.3(5)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0798
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25758
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.709
_diffrn_reflns_theta_min         2.626
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.099
_exptl_crystal_colour            'Yellow colour'
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       Niddle
_exptl_crystal_F_000             324
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3863
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0581
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0673P)²+0.2250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1493
_refine_ls_wR_factor_ref         0.1722
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2724
_reflns_number_total             3863
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ob00855a2.cif
_cod_data_source_block           mo_SR_01_0m
_cod_depositor_comments          'Adding full bibliography for 7156928.cif.'
_cod_original_cell_volume        764.3(4)
_cod_database_code               7156928
_shelx_shelxl_version_number     2014/7
_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.
;
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
O4 O 0.21559(19) 0.63230(16) 0.25464(8) 0.0544(3) Uani 1 1 d . .
O1 O 0.9213(3) 0.1593(2) 0.55316(10) 0.0780(5) Uani 1 1 d . .
O3 O -0.0347(2) 0.5216(2) 0.31035(10) 0.0784(5) Uani 1 1 d . .
C10 C 0.4263(4) 0.6731(3) 0.09901(16) 0.0945(9) Uani 1 1 d . .
H10A H 0.4942 0.7214 0.0516 0.142 Uiso 1 1 calc R U
H10B H 0.4050 0.5668 0.0820 0.142 Uiso 1 1 calc R U
H10C H 0.5161 0.6410 0.1470 0.142 Uiso 1 1 calc R U
O5 O 0.1660(3) 1.2032(2) 0.04364(10) 0.0770(5) Uani 1 1 d . .
O2 O 0.6893(3) 0.0534(2) 0.61661(10) 0.0918(5) Uani 1 1 d . .
N1 N 0.7467(3) 0.1419(2) 0.55888(9) 0.0607(4) Uani 1 1 d . .
C3 C 0.5919(3) 0.2359(2) 0.49296(10) 0.0505(4) Uani 1 1 d . .
C4 C 0.6654(3) 0.3078(3) 0.41934(11) 0.0580(4) Uani 1 1 d . .
H4 H 0.8099 0.2926 0.4101 0.070 Uiso 1 1 calc R U
C5 C 0.5192(3) 0.4036(3) 0.35904(11) 0.0560(4) Uani 1 1 d . .
H5 H 0.5653 0.4552 0.3092 0.067 Uiso 1 1 calc R U
C6 C 0.3060(3) 0.4229(2) 0.37233(10) 0.0480(4) Uani 1 1 d . .
C7 C 0.1420(3) 0.5290(2) 0.31010(11) 0.0530(4) Uani 1 1 d . .
C8 C 0.0704(3) 0.7491(2) 0.19082(11) 0.0544(4) Uani 1 1 d . .
H8 H -0.0044 0.6829 0.1638 0.065 Uiso 1 1 calc R U
C13 C -0.0875(3) 0.9191(3) 0.23222(12) 0.0582(5) Uani 1 1 d . .
H13A H -0.2317 0.9436 0.2150 0.070 Uiso 1 1 calc R U
H13B H -0.0880 0.9031 0.2946 0.070 Uiso 1 1 calc R U
C12 C -0.0122(3) 1.0752(2) 0.20087(10) 0.0507(4) Uani 1 1 d . .
H12 H -0.0147 1.1477 0.2495 0.061 Uiso 1 1 calc R U
C14 C -0.1474(3) 1.1979(3) 0.12981(13) 0.0609(5) Uani 1 1 d . .
H14A H -0.1772 1.1230 0.0899 0.073 Uiso 1 1 calc R U
H14B H -0.2835 1.2761 0.1555 0.073 Uiso 1 1 calc R U
C15 C -0.0351(4) 1.3133(3) 0.08131(16) 0.0772(6) Uani 1 1 d . .
H15A H -0.1242 1.3875 0.0365 0.093 Uiso 1 1 calc R U
H15B H -0.0132 1.3939 0.1203 0.093 Uiso 1 1 calc R U
C2 C 0.3813(3) 0.2515(3) 0.50815(12) 0.0607(5) Uani 1 1 d . .
H2 H 0.3361 0.2004 0.5584 0.073 Uiso 1 1 calc R U
C1 C 0.2377(3) 0.3453(3) 0.44679(12) 0.0590(5) Uani 1 1 d . .
H1A H 0.0943 0.3564 0.4555 0.071 Uiso 1 1 calc R U
C9 C 0.2105(3) 0.8154(2) 0.12493(11) 0.0565(5) Uani 1 1 d . .
H9 H 0.1309 0.8589 0.0728 0.068 Uiso 1 1 calc R U
C11 C 0.2197(3) 0.9800(3) 0.16615(11) 0.0530(4) Uani 1 1 d . .
H11 H 0.3098 0.9366 0.2155 0.064 Uiso 1 1 calc R U
C16 C 0.3064(4) 1.1051(3) 0.10869(15) 0.0764(6) Uani 1 1 d . .
H16A H 0.3305 1.1909 0.1440 0.092 Uiso 1 1 calc R U
H16B H 0.4437 1.0334 0.0815 0.092 Uiso 1 1 calc R U
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
C7 O4 C8 117.99(14)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C15 O5 C16 110.48(17)
O2 N1 O1 124.06(18)
O2 N1 C3 117.25(18)
O1 N1 C3 118.69(16)
C2 C3 C4 122.64(16)
C2 C3 N1 119.25(16)
C4 C3 N1 118.10(17)
C3 C4 C5 118.43(17)
C3 C4 H4 120.8
C5 C4 H4 120.8
C6 C5 C4 120.54(16)
C6 C5 H5 119.7
C4 C5 H5 119.7
C5 C6 C1 119.55(16)
C5 C6 C7 122.29(15)
C1 C6 C7 118.15(16)
O3 C7 O4 124.29(17)
O3 C7 C6 124.19(16)
O4 C7 C6 111.51(15)
O4 C8 C9 105.92(14)
O4 C8 C13 110.29(14)
C9 C8 C13 105.85(14)
O4 C8 H8 111.5
C9 C8 H8 111.5
C13 C8 H8 111.5
C12 C13 C8 106.55(14)
C12 C13 H13A 110.4
C8 C13 H13A 110.4
C12 C13 H13B 110.4
C8 C13 H13B 110.4
H13A C13 H13B 108.6
C13 C12 C11 103.94(14)
C13 C12 C14 112.61(15)
C11 C12 C14 110.55(14)
C13 C12 H12 109.9
C11 C12 H12 109.9
C14 C12 H12 109.9
C15 C14 C12 111.82(17)
C15 C14 H14A 109.3
C12 C14 H14A 109.3
C15 C14 H14B 109.3
C12 C14 H14B 109.3
H14A C14 H14B 107.9
O5 C15 C14 110.77(16)
O5 C15 H15A 109.5
C14 C15 H15A 109.5
O5 C15 H15B 109.5
C14 C15 H15B 109.5
H15A C15 H15B 108.1
C3 C2 C1 118.29(16)
C3 C2 H2 120.9
C1 C2 H2 120.9
C2 C1 C6 120.54(17)
C2 C1 H1A 119.7
C6 C1 H1A 119.7
C11 C9 C10 115.70(19)
C11 C9 C8 102.41(14)
C10 C9 C8 115.31(16)
C11 C9 H9 107.6
C10 C9 H9 107.6
C8 C9 H9 107.6
C16 C11 C9 116.40(16)
C16 C11 C12 112.91(16)
C9 C11 C12 103.18(14)
C16 C11 H11 108.0
C9 C11 H11 108.0
C12 C11 H11 108.0
O5 C16 C11 113.01(17)
O5 C16 H16A 109.0
C11 C16 H16A 109.0
O5 C16 H16B 109.0
C11 C16 H16B 109.0
H16A C16 H16B 107.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 C7 1.327(2)
O4 C8 1.469(2)
O1 N1 1.219(2)
O3 C7 1.204(2)
C10 C9 1.521(3)
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
O5 C15 1.419(3)
O5 C16 1.423(3)
O2 N1 1.217(2)
N1 C3 1.478(2)
C3 C2 1.371(3)
C3 C4 1.373(2)
C4 C5 1.387(2)
C4 H4 0.9300
C5 C6 1.378(2)
C5 H5 0.9300
C6 C1 1.390(2)
C6 C7 1.495(2)
C8 C9 1.521(3)
C8 C13 1.527(3)
C8 H8 0.9800
C13 C12 1.524(3)
C13 H13A 0.9700
C13 H13B 0.9700
C12 C11 1.531(2)
C12 C14 1.534(2)
C12 H12 0.9800
C14 C15 1.502(3)
C14 H14A 0.9700
C14 H14B 0.9700
C15 H15A 0.9700
C15 H15B 0.9700
C2 C1 1.385(3)
C2 H2 0.9300
C1 H1A 0.9300
C9 C11 1.517(3)
C9 H9 0.9800
C11 C16 1.517(3)
C11 H11 0.9800
C16 H16A 0.9700
C16 H16B 0.9700
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
C11 H11 O2 0.98 2.63 3.465(3) 143.7 2_666
C13 H13B O1 0.97 2.64 3.553(3) 156.1 2_666
C11 H11 O2 0.98 2.63 3.465(3) 143.7 2_666
C13 H13B O1 0.97 2.64 3.553(3) 156.1 2_666
C13 H13B O1 0.97 2.64 3.553(3) 156.1 2_666
C11 H11 O2 0.98 2.63 3.465(3) 143.7 2_666
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
O2 N1 C3 C2 13.2(2)
O1 N1 C3 C2 -165.69(17)
O2 N1 C3 C4 -168.12(18)
O1 N1 C3 C4 12.9(2)
C2 C3 C4 C5 1.6(3)
N1 C3 C4 C5 -177.00(16)
C3 C4 C5 C6 -1.2(3)
C4 C5 C6 C1 -0.1(3)
C4 C5 C6 C7 178.43(17)
C8 O4 C7 O3 1.8(3)
C8 O4 C7 C6 -178.23(13)
C5 C6 C7 O3 165.4(2)
C1 C6 C7 O3 -16.0(3)
C5 C6 C7 O4 -14.6(2)
C1 C6 C7 O4 163.96(16)
C7 O4 C8 C9 -167.28(14)
C7 O4 C8 C13 78.62(19)
O4 C8 C13 C12 104.78(16)
C9 C8 C13 C12 -9.36(18)
C8 C13 C12 C11 -16.88(18)
C8 C13 C12 C14 102.80(16)
C13 C12 C14 C15 -162.58(16)
C11 C12 C14 C15 -46.8(2)
C16 O5 C15 C14 -64.4(2)
C12 C14 C15 O5 58.3(2)
C4 C3 C2 C1 -0.7(3)
N1 C3 C2 C1 177.91(16)
C3 C2 C1 C6 -0.7(3)
C5 C6 C1 C2 1.1(3)
C7 C6 C1 C2 -177.53(16)
O4 C8 C9 C11 -85.05(15)
C13 C8 C9 C11 32.07(17)
O4 C8 C9 C10 41.5(2)
C13 C8 C9 C10 158.61(19)
C10 C9 C11 C16 66.9(2)
C8 C9 C11 C16 -166.85(15)
C10 C9 C11 C12 -168.90(15)
C8 C9 C11 C12 -42.62(16)
C13 C12 C11 C16 163.44(16)
C14 C12 C11 C16 42.4(2)
C13 C12 C11 C9 36.94(16)
C14 C12 C11 C9 -84.13(17)
C15 O5 C16 C11 60.1(2)
C9 C11 C16 O5 69.5(2)
C12 C11 C16 O5 -49.6(2)
