#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/17/7151763.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_7151763
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         'C21 H27 N O5, H2 O'
_chemical_formula_sum            'C21 H29 N O6'
_chemical_formula_weight         391.45
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 104.148(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2818(1)
_cell_length_b                   33.8728(3)
_cell_length_c                   8.3252(1)
_cell_measurement_reflns_used    16347
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      71.1645
_cell_measurement_theta_min      2.6044
_cell_volume                     1991.17(4)
_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      173(2)
_diffrn_detector_area_resol_mean 8.2556
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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     1.54184
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0115
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            25468
_diffrn_reflns_theta_full        71.29
_diffrn_reflns_theta_max         71.29
_diffrn_reflns_theta_min         5.22
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.784
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75352
_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    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3808
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0424
_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)+(0.0673P)²+0.7003P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1224
_refine_ls_wR_factor_ref         0.1248
_reflns_number_gt                3426
_reflns_number_total             3808
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob00895h.txt
_cod_data_source_block           16
_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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7151763
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.41313(16) 0.09730(3) 1.54419(14) 0.0420(3) Uani 1 1 d . . .
C2 C 1.3420(3) 0.05756(5) 1.5425(2) 0.0469(4) Uani 1 1 d . . .
H2A H 1.3923 0.0410 1.4651 0.056 Uiso 1 1 calc R . .
H2B H 1.3813 0.0458 1.6546 0.056 Uiso 1 1 calc R . .
O3 O 1.13935(17) 0.05968(3) 1.48998(16) 0.0465(3) Uani 1 1 d . . .
C4 C 1.1013(2) 0.09581(4) 1.41372(18) 0.0340(3) Uani 1 1 d . . .
C5 C 0.9337(2) 0.10909(4) 1.31584(18) 0.0327(3) Uani 1 1 d . . .
H5A H 0.8236 0.0930 1.2926 0.039 Uiso 1 1 calc R . .
C6 C 0.9306(2) 0.14778(4) 1.25042(17) 0.0284(3) Uani 1 1 d . . .
C7 C 1.0962(2) 0.17050(4) 1.29090(18) 0.0311(3) Uani 1 1 d . . .
H7A H 1.0930 0.1966 1.2487 0.037 Uiso 1 1 calc R . .
C8 C 1.2657(2) 0.15627(5) 1.39084(18) 0.0337(3) Uani 1 1 d . . .
H8A H 1.3767 0.1721 1.4175 0.040 Uiso 1 1 calc R . .
C9 C 1.2652(2) 0.11843(5) 1.44885(18) 0.0332(3) Uani 1 1 d . . .
C10 C 0.7578(2) 0.16274(4) 1.13138(17) 0.0283(3) Uani 1 1 d . . .
C11 C 0.7841(2) 0.19718(4) 1.02460(18) 0.0289(3) Uani 1 1 d . . .
H11A H 0.8448 0.2196 1.0965 0.035 Uiso 1 1 calc R . .
O12 O 0.90202(13) 0.18561(3) 0.91645(12) 0.0298(2) Uani 1 1 d . . .
C13 C 0.8673(2) 0.21328(4) 0.78293(18) 0.0320(3) Uani 1 1 d . . .
O14 O 0.68022(15) 0.22895(3) 0.77235(13) 0.0353(3) Uani 1 1 d . . .
C15 C 0.6069(2) 0.21175(4) 0.90120(18) 0.0316(3) Uani 1 1 d . . .
H15A H 0.5422 0.2324 0.9536 0.038 Uiso 1 1 calc R . .
C16 C 0.4720(2) 0.17834(5) 0.83645(19) 0.0339(3) Uani 1 1 d . . .
H16A H 0.5333 0.1596 0.7744 0.041 Uiso 1 1 calc R . .
H16B H 0.3577 0.1890 0.7587 0.041 Uiso 1 1 calc R . .
C17 C 0.4135(2) 0.15633(4) 0.97597(19) 0.0330(3) Uani 1 1 d . . .
H17A H 0.3259 0.1733 1.0216 0.040 Uiso 1 1 calc R . .
C18 C 0.5856(2) 0.14654(4) 1.11228(18) 0.0319(3) Uani 1 1 d . . .
H18A H 0.5710 0.1273 1.1912 0.038 Uiso 1 1 calc R . .
C19 C 1.0071(2) 0.24698(5) 0.8201(2) 0.0396(4) Uani 1 1 d . . .
H19A H 0.9973 0.2602 0.9225 0.059 Uiso 1 1 calc R . .
H19B H 0.9790 0.2659 0.7284 0.059 Uiso 1 1 calc R . .
H19C H 1.1358 0.2367 0.8335 0.059 Uiso 1 1 calc R . .
C20 C 0.8705(2) 0.19122(5) 0.6259(2) 0.0392(4) Uani 1 1 d . . .
H20A H 0.7763 0.1700 0.6084 0.059 Uiso 1 1 calc R . .
H20B H 0.9966 0.1799 0.6357 0.059 Uiso 1 1 calc R . .
H20C H 0.8405 0.2095 0.5317 0.059 Uiso 1 1 calc R . .
C21 C 0.3087(2) 0.11871(5) 0.9012(2) 0.0367(4) Uani 1 1 d . . .
H21A H 0.2115 0.1262 0.8002 0.044 Uiso 1 1 calc R . .
H21B H 0.4004 0.1011 0.8664 0.044 Uiso 1 1 calc R . .
C22 C 0.2130(2) 0.09560(5) 1.0128(2) 0.0387(4) Uani 1 1 d . . .
H22A H 0.3043 0.0902 1.1199 0.046 Uiso 1 1 calc R . .
H22B H 0.1063 0.1110 1.0349 0.046 Uiso 1 1 calc R . .
N23 N 0.14246(19) 0.05805(4) 0.92978(18) 0.0392(3) Uani 1 1 d . . .
O24 O 0.27860(19) 0.03201(4) 0.9344(2) 0.0587(4) Uani 1 1 d . . .
C25 C -0.0310(2) 0.05122(5) 0.8522(2) 0.0430(4) Uani 1 1 d . . .
C26 C -0.0778(3) 0.01234(6) 0.7680(3) 0.0571(5) Uani 1 1 d . . .
H26A H -0.0647 0.0142 0.6538 0.086 Uiso 1 1 calc R . .
H26B H -0.2084 0.0051 0.7671 0.086 Uiso 1 1 calc R . .
H26C H 0.0088 -0.0079 0.8277 0.086 Uiso 1 1 calc R . .
C27 C -0.1836(3) 0.08054(7) 0.8411(3) 0.0644(6) Uani 1 1 d . . .
H27A H -0.2707 0.0715 0.9063 0.097 Uiso 1 1 calc R . .
H27B H -0.2529 0.0837 0.7251 0.097 Uiso 1 1 calc R . .
H27C H -0.1285 0.1059 0.8844 0.097 Uiso 1 1 calc R . .
O30 O 0.5903(3) 0.03428(5) 1.2076(3) 0.0794(5) Uani 1 1 d D . .
H30A H 0.486(3) 0.0341(12) 1.124(3) 0.145(15) Uiso 1 1 d D . .
H30B H 0.658(4) 0.0128(6) 1.196(5) 0.121(13) Uiso 1 1 d 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'
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
C9 O1 C2 104.62(12) . . ?
O3 C2 O1 107.24(13) . . ?
C4 O3 C2 105.15(12) . . ?
C5 C4 O3 128.14(14) . . ?
C5 C4 C9 122.69(14) . . ?
O3 C4 C9 109.17(13) . . ?
C4 C5 C6 117.49(14) . . ?
C7 C6 C5 118.90(13) . . ?
C7 C6 C10 120.77(13) . . ?
C5 C6 C10 120.18(13) . . ?
C8 C7 C6 122.56(14) . . ?
C9 C8 C7 117.08(14) . . ?
C8 C9 O1 128.48(14) . . ?
C8 C9 C4 121.23(14) . . ?
O1 C9 C4 110.28(13) . . ?
C18 C10 C6 123.59(13) . . ?
C18 C10 C11 119.74(13) . . ?
C6 C10 C11 116.64(12) . . ?
O12 C11 C10 109.81(11) . . ?
O12 C11 C15 101.69(11) . . ?
C10 C11 C15 116.14(12) . . ?
C13 O12 C11 106.76(10) . . ?
O12 C13 O14 105.87(11) . . ?
O12 C13 C19 110.74(12) . . ?
O14 C13 C19 108.26(12) . . ?
O12 C13 C20 108.15(12) . . ?
O14 C13 C20 110.04(12) . . ?
C19 C13 C20 113.50(13) . . ?
C15 O14 C13 108.86(10) . . ?
O14 C15 C16 111.49(12) . . ?
O14 C15 C11 103.16(11) . . ?
C16 C15 C11 111.61(12) . . ?
C15 C16 C17 111.90(12) . . ?
C18 C17 C16 110.18(12) . . ?
C18 C17 C21 111.21(13) . . ?
C16 C17 C21 107.47(13) . . ?
C10 C18 C17 125.44(14) . . ?
C22 C21 C17 116.03(13) . . ?
N23 C22 C21 108.56(13) . . ?
C25 N23 O24 122.04(15) . . ?
C25 N23 C22 125.01(14) . . ?
O24 N23 C22 112.85(13) . . ?
N23 C25 C27 122.70(16) . . ?
N23 C25 C26 118.46(17) . . ?
C27 C25 C26 118.83(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
O1 C9 1.3727(18) . ?
O1 C2 1.441(2) . ?
C2 O3 1.435(2) . ?
O3 C4 1.3753(19) . ?
C4 C5 1.367(2) . ?
C4 C9 1.388(2) . ?
C5 C6 1.417(2) . ?
C6 C7 1.401(2) . ?
C6 C10 1.487(2) . ?
C7 C8 1.395(2) . ?
C8 C9 1.370(2) . ?
C10 C18 1.342(2) . ?
C10 C11 1.507(2) . ?
C11 O12 1.4422(17) . ?
C11 C15 1.522(2) . ?
O12 C13 1.4285(17) . ?
C13 O14 1.4443(17) . ?
C13 C19 1.510(2) . ?
C13 C20 1.511(2) . ?
O14 C15 1.4336(18) . ?
C15 C16 1.509(2) . ?
C16 C17 1.526(2) . ?
C17 C18 1.508(2) . ?
C17 C21 1.537(2) . ?
C21 C22 1.509(2) . ?
C22 N23 1.479(2) . ?
N23 C25 1.291(2) . ?
N23 O24 1.3205(18) . ?
C25 C27 1.477(3) . ?
C25 C26 1.492(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190611
