#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/17/7151765.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_7151765
loop_
_publ_author_name
'Haning, Helmut'
'Giró-Mañas, Carles'
'Paddock, Victoria L.'
'Bochet, Christian G.'
'White, Andrew J. P.'
'Bernardinelli, Gerald'
'Mann, Inderjit'
'Oppolzer, Wolfang'
'Spivey, Alan C.'
_publ_section_title
;
 Total synthesis of the Amaryllidaceae alkaloid clivonine.
;
_journal_issue                   8
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2809
_journal_page_last               2820
_journal_paper_doi               10.1039/c0ob00895h
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C25 H26 Cl N O5'
_chemical_formula_sum            'C25 H26 Cl N O5'
_chemical_formula_weight         455.92
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.804(3)
_cell_angle_beta                 98.740(3)
_cell_angle_gamma                102.130(3)
_cell_formula_units_Z            2
_cell_length_a                   6.0988(2)
_cell_length_b                   11.8551(4)
_cell_length_c                   16.3205(5)
_cell_measurement_reflns_used    7226
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      71.2573
_cell_measurement_theta_min      2.8355
_cell_volume                     1100.31(7)
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd'
_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 8.2556
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'OD Xcalibur PX Ultra'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54248
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16799
_diffrn_reflns_theta_full        71.53
_diffrn_reflns_theta_max         71.53
_diffrn_reflns_theta_min         2.84
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.854
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.4 (release 27-04-2006 CrysAlis171 .NET)
(compiled Apr 27 2007,17:53:11)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0012(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4218
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0368
_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)+(0.0696P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1087
_reflns_number_gt                3060
_reflns_number_total             4218
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob00895h.txt
_cod_data_source_block           28
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        1100.31(6)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7151765
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.6775(2) 0.74922(11) 0.62301(8) 0.0489(3) Uani 1 1 d . . .
C2 C 0.4999(2) 0.79823(12) 0.66015(9) 0.0443(3) Uani 1 1 d . . .
H2A H 0.3540 0.7370 0.6437 0.053 Uiso 1 1 calc R . .
C3 C 0.5715(3) 0.84321(12) 0.75940(9) 0.0440(3) Uani 1 1 d . . .
H3A H 0.7290 0.8932 0.7736 0.053 Uiso 1 1 calc R . .
C4 C 0.4197(3) 0.92203(13) 0.79310(9) 0.0496(4) Uani 1 1 d . . .
H4A H 0.2645 0.8728 0.7871 0.060 Uiso 1 1 calc R . .
O5 O 0.5154(2) 0.98062(10) 0.88134(7) 0.0661(3) Uani 1 1 d . . .
C6 C 0.4775(3) 1.09754(14) 0.89679(10) 0.0568(4) Uani 1 1 d . . .
O7 O 0.4979(2) 1.13045(9) 0.81909(7) 0.0603(3) Uani 1 1 d . . .
C8 C 0.4090(3) 1.02458(12) 0.75032(10) 0.0504(4) Uani 1 1 d . . .
H8A H 0.2491 1.0192 0.7257 0.061 Uiso 1 1 calc R . .
C9 C 0.5481(3) 1.02489(13) 0.68173(10) 0.0551(4) Uani 1 1 d . . .
H9A H 0.7099 1.0444 0.7078 0.066 Uiso 1 1 calc R . .
H9B H 0.5226 1.0853 0.6525 0.066 Uiso 1 1 calc R . .
C10 C 0.4797(3) 0.90169(13) 0.61654(9) 0.0509(4) Uani 1 1 d . . .
H10A H 0.3214 0.8868 0.5854 0.061 Uiso 1 1 calc R . .
C11 C 0.6372(3) 0.89388(15) 0.55215(10) 0.0587(4) Uani 1 1 d . . .
H11A H 0.5539 0.8434 0.4961 0.070 Uiso 1 1 calc R . .
H11B H 0.7064 0.9725 0.5464 0.070 Uiso 1 1 calc R . .
C12 C 0.8161(3) 0.83948(14) 0.59109(10) 0.0573(4) Uani 1 1 d . . .
H12A H 0.8929 0.8035 0.5483 0.069 Uiso 1 1 calc R . .
H12B H 0.9293 0.8984 0.6374 0.069 Uiso 1 1 calc R . .
C13 C 0.7430(3) 0.64718(13) 0.62620(9) 0.0481(4) Uani 1 1 d . . .
O13 O 0.9369(2) 0.63992(11) 0.61832(8) 0.0647(3) Uani 1 1 d . . .
C14 C 0.5719(3) 0.54039(12) 0.63214(9) 0.0467(3) Uani 1 1 d . . .
C15 C 0.3448(3) 0.51077(13) 0.58964(9) 0.0490(4) Uani 1 1 d . . .
H15A H 0.2936 0.5604 0.5584 0.059 Uiso 1 1 calc R . .
C16 C 0.1933(3) 0.40800(14) 0.59324(10) 0.0551(4) Uani 1 1 d . . .
H16A H 0.0407 0.3884 0.5649 0.066 Uiso 1 1 calc R . .
C17 C 0.2722(3) 0.33551(14) 0.63926(10) 0.0575(4) Uani 1 1 d . . .
Cl Cl 0.07925(10) 0.20707(4) 0.64440(4) 0.0869(2) Uani 1 1 d . . .
C18 C 0.4986(3) 0.36074(14) 0.68048(10) 0.0604(4) Uani 1 1 d . . .
H18A H 0.5494 0.3098 0.7105 0.072 Uiso 1 1 calc R . .
C19 C 0.6480(3) 0.46329(14) 0.67621(10) 0.0537(4) Uani 1 1 d . . .
H19A H 0.8016 0.4811 0.7031 0.064 Uiso 1 1 calc R . .
C20 C 0.5697(3) 0.74251(12) 0.80238(8) 0.0462(3) Uani 1 1 d . . .
C21 C 0.3605(3) 0.65947(13) 0.79514(9) 0.0502(4) Uani 1 1 d . . .
H21A H 0.2231 0.6662 0.7654 0.060 Uiso 1 1 calc R . .
C22 C 0.3682(3) 0.56878(13) 0.83362(10) 0.0581(4) Uani 1 1 d . . .
O23 O 0.1899(3) 0.47615(12) 0.83291(9) 0.0839(4) Uani 1 1 d . . .
C24 C 0.2926(6) 0.4046(2) 0.87973(14) 0.1003(8) Uani 1 1 d . . .
H24A H 0.2267 0.4012 0.9299 0.120 Uiso 1 1 calc R . .
H24B H 0.2620 0.3237 0.8438 0.120 Uiso 1 1 calc R . .
O25 O 0.5333(3) 0.45505(13) 0.90566(9) 0.0915(5) Uani 1 1 d . . .
C26 C 0.5709(4) 0.55670(15) 0.87719(10) 0.0645(5) Uani 1 1 d . . .
C27 C 0.7759(4) 0.63628(16) 0.88608(10) 0.0673(5) Uani 1 1 d . . .
H27A H 0.9120 0.6284 0.9159 0.081 Uiso 1 1 calc R . .
C28 C 0.7700(3) 0.73045(14) 0.84774(9) 0.0560(4) Uani 1 1 d . . .
H28A H 0.9061 0.7870 0.8530 0.067 Uiso 1 1 calc R . .
C29 C 0.2436(4) 1.09439(18) 0.91663(14) 0.0775(6) Uani 1 1 d . . .
H29A H 0.1290 1.0399 0.8696 0.116 Uiso 1 1 calc R . .
H29B H 0.2179 1.1729 0.9250 0.116 Uiso 1 1 calc R . .
H29C H 0.2345 1.0683 0.9680 0.116 Uiso 1 1 calc R . .
C30 C 0.6654(4) 1.18121(18) 0.96805(12) 0.0800(6) Uani 1 1 d . . .
H30A H 0.8112 1.1799 0.9531 0.120 Uiso 1 1 calc R . .
H30B H 0.6598 1.1564 1.0200 0.120 Uiso 1 1 calc R . .
H30C H 0.6453 1.2609 0.9766 0.120 Uiso 1 1 calc R . .
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'
Cl Cl 0.3639 0.7018 '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
C13 N1 C12 119.75(13) . . ?
C13 N1 C2 130.30(12) . . ?
C12 N1 C2 109.19(12) . . ?
N1 C2 C3 111.32(12) . . ?
N1 C2 C10 103.24(11) . . ?
C3 C2 C10 112.54(11) . . ?
C20 C3 C4 111.66(12) . . ?
C20 C3 C2 112.79(11) . . ?
C4 C3 C2 109.64(12) . . ?
O5 C4 C3 108.59(12) . . ?
O5 C4 C8 104.36(11) . . ?
C3 C4 C8 114.32(12) . . ?
C4 O5 C6 107.23(12) . . ?
O7 C6 O5 104.07(11) . . ?
O7 C6 C30 108.80(15) . . ?
O5 C6 C30 109.12(15) . . ?
O7 C6 C29 112.06(15) . . ?
O5 C6 C29 110.22(15) . . ?
C30 C6 C29 112.22(15) . . ?
C6 O7 C8 107.35(11) . . ?
O7 C8 C9 110.71(13) . . ?
O7 C8 C4 104.42(12) . . ?
C9 C8 C4 112.77(12) . . ?
C8 C9 C10 110.19(13) . . ?
C11 C10 C9 111.64(13) . . ?
C11 C10 C2 105.05(12) . . ?
C9 C10 C2 112.48(12) . . ?
C12 C11 C10 103.43(13) . . ?
N1 C12 C11 101.78(13) . . ?
O13 C13 N1 120.32(15) . . ?
O13 C13 C14 119.90(14) . . ?
N1 C13 C14 119.59(13) . . ?
C15 C14 C19 119.08(15) . . ?
C15 C14 C13 122.14(14) . . ?
C19 C14 C13 118.58(14) . . ?
C16 C15 C14 120.60(15) . . ?
C17 C16 C15 118.90(16) . . ?
C16 C17 C18 121.99(16) . . ?
C16 C17 Cl 118.56(14) . . ?
C18 C17 Cl 119.45(14) . . ?
C17 C18 C19 118.55(16) . . ?
C18 C19 C14 120.83(16) . . ?
C28 C20 C21 119.83(15) . . ?
C28 C20 C3 120.92(14) . . ?
C21 C20 C3 119.25(14) . . ?
C22 C21 C20 117.13(16) . . ?
C21 C22 O23 127.60(18) . . ?
C21 C22 C26 122.23(17) . . ?
O23 C22 C26 110.11(15) . . ?
C22 O23 C24 104.85(18) . . ?
O25 C24 O23 109.60(17) . . ?
C26 O25 C24 104.79(17) . . ?
C27 C26 O25 127.31(19) . . ?
C27 C26 C22 122.04(16) . . ?
O25 C26 C22 110.62(18) . . ?
C26 C27 C28 116.28(17) . . ?
C20 C28 C27 122.47(17) . . ?
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
N1 C13 1.3605(19) . ?
N1 C12 1.460(2) . ?
N1 C2 1.4784(18) . ?
C2 C3 1.5502(19) . ?
C2 C10 1.565(2) . ?
C3 C20 1.512(2) . ?
C3 C4 1.5242(19) . ?
C4 O5 1.4241(18) . ?
C4 C8 1.538(2) . ?
O5 C6 1.4268(18) . ?
C6 O7 1.4222(19) . ?
C6 C30 1.502(2) . ?
C6 C29 1.505(3) . ?
O7 C8 1.4261(17) . ?
C8 C9 1.504(2) . ?
C9 C10 1.5360(19) . ?
C10 C11 1.529(2) . ?
C11 C12 1.509(2) . ?
C13 O13 1.2271(18) . ?
C13 C14 1.494(2) . ?
C14 C15 1.385(2) . ?
C14 C19 1.392(2) . ?
C15 C16 1.384(2) . ?
C16 C17 1.373(2) . ?
C17 C18 1.380(3) . ?
C17 Cl 1.7446(17) . ?
C18 C19 1.380(2) . ?
C20 C28 1.380(2) . ?
C20 C21 1.409(2) . ?
C21 C22 1.365(2) . ?
C22 O23 1.370(2) . ?
C22 C26 1.381(3) . ?
O23 C24 1.436(3) . ?
C24 O25 1.422(3) . ?
O25 C26 1.373(2) . ?
C26 C27 1.365(3) . ?
C27 C28 1.400(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 53360538
