#------------------------------------------------------------------------------
#$Date: 2017-11-27 11:31:21 +0200 (Mon, 27 Nov 2017) $
#$Revision: 203612 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/82/1548227.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_1548227
loop_
_publ_author_name
'Zhi-Wei Jiao'
'Yong-Qiang Tu'
'Qing Zhang'
'Wen-Xing Liu'
'Shu-Yu Zhang'
'Shao-Hua Wang'
'Fu-Min Zhang'
'Sen Jiang'
_publ_section_title
;
 Tandem C-H oxidation/cyclization/rearrangement and its application to
 asymmetric syntheses of (-)-brussonol and (-)-przewalskine E
;
_journal_name_full               'Nature Communications'
_journal_page_first              7332
_journal_paper_doi               10.1038/ncomms8332
_journal_volume                  6
_journal_year                    2015
_chemical_formula_moiety         'C18 H22 O5'
_chemical_formula_sum            'C18 H22 O5'
_chemical_formula_weight         318.35
_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
_atom_sites_solution_primary     direct
_cell_angle_alpha                104.353(11)
_cell_angle_beta                 109.179(10)
_cell_angle_gamma                98.133(10)
_cell_formula_units_Z            2
_cell_length_a                   8.7788(10)
_cell_length_b                   9.8167(13)
_cell_length_c                   10.4098(11)
_cell_measurement_reflns_used    2923
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      70.6450
_cell_measurement_theta_min      4.7070
_cell_volume                     796.13(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0325749000
_diffrn_orient_matrix_UB_12      0.1541556000
_diffrn_orient_matrix_UB_13      0.1010545000
_diffrn_orient_matrix_UB_21      -0.1636679000
_diffrn_orient_matrix_UB_22      0.0182552000
_diffrn_orient_matrix_UB_23      -0.1007411000
_diffrn_orient_matrix_UB_31      -0.0940279000
_diffrn_orient_matrix_UB_32      -0.0612705000
_diffrn_orient_matrix_UB_33      0.0828780000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6122
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.667
_diffrn_reflns_theta_min         4.739
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       plate
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2999
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0480
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0840P)²+0.2627P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1350
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2805
_reflns_number_total             2999
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ncomms8332-s4.cif
_cod_data_source_block           jiaozhw1223
_cod_original_cell_volume        796.14(18)
_cod_database_code               1548227
_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.
;
_reflns_odcompleteness_completeness 92.0
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17)
2.d X=CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C)
;
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.12834(13) 0.41998(12) 0.57874(11) 0.0306(3) Uani 1 1 d . . . . .
O2 O 0.29734(12) 0.68714(11) 0.80355(12) 0.0278(3) Uani 1 1 d . . . . .
O3 O 0.33229(12) 0.70089(11) 1.07668(11) 0.0272(3) Uani 1 1 d . . . . .
O4 O 0.04566(12) 0.05190(10) 0.69332(11) 0.0247(3) Uani 1 1 d . . . . .
O5 O -0.39837(16) -0.13585(13) 0.48930(13) 0.0421(3) Uani 1 1 d . . . . .
C1 C 0.09405(16) 0.31079(15) 0.74930(14) 0.0199(3) Uani 1 1 d . . . . .
C2 C 0.15550(16) 0.43315(15) 0.71930(14) 0.0215(3) Uani 1 1 d . . . . .
C3 C 0.23404(16) 0.56414(15) 0.82921(15) 0.0219(3) Uani 1 1 d . . . . .
C4 C 0.25391(16) 0.56996(15) 0.96936(15) 0.0213(3) Uani 1 1 d . . . . .
C5 C 0.19171(16) 0.44947(16) 1.00152(14) 0.0218(3) Uani 1 1 d . . . . .
C6 C 0.10821(16) 0.31981(15) 0.88899(14) 0.0201(3) Uani 1 1 d . . . . .
C7 C 0.03723(17) 0.18524(15) 0.91706(15) 0.0235(3) Uani 1 1 d . . . . .
H7A H -0.0413 0.2072 0.9646 0.028 Uiso 1 1 calc R . . . .
H7B H 0.1286 0.1575 0.9829 0.028 Uiso 1 1 calc R . . . .
C8 C -0.05296(17) 0.05841(15) 0.77915(15) 0.0226(3) Uani 1 1 d . . . . .
H8 H -0.0710 -0.0343 0.8019 0.027 Uiso 1 1 calc R . . . .
C9 C -0.22178(17) 0.07749(14) 0.68219(14) 0.0214(3) Uani 1 1 d . . . . .
H9 H -0.2612 0.1512 0.7402 0.026 Uiso 1 1 calc R . . . .
C10 C -0.17559(18) 0.13568(15) 0.57208(15) 0.0242(3) Uani 1 1 d . . . . .
H10A H -0.2243 0.0624 0.4757 0.029 Uiso 1 1 calc R . . . .
H10B H -0.2134 0.2251 0.5664 0.029 Uiso 1 1 calc R . . . .
C11 C 0.01432(17) 0.16666(15) 0.63226(14) 0.0224(3) Uani 1 1 d . . . . .
H11 H 0.0578 0.1611 0.5540 0.027 Uiso 1 1 calc R . . . .
C12 C 0.2700(2) 0.4573(2) 0.5455(2) 0.0423(4) Uani 1 1 d . . . . .
H12A H 0.2397 0.4195 0.4417 0.063 Uiso 1 1 calc GR . . . .
H12B H 0.3578 0.4152 0.5942 0.063 Uiso 1 1 calc GR . . . .
H12C H 0.3101 0.5631 0.5777 0.063 Uiso 1 1 calc GR . . . .
C13 C 0.17497(19) 0.76467(17) 0.75593(17) 0.0304(3) Uani 1 1 d . . . . .
H13A H 0.0904 0.7046 0.6627 0.046 Uiso 1 1 calc GR . . . .
H13B H 0.2284 0.8545 0.7468 0.046 Uiso 1 1 calc GR . . . .
H13C H 0.1224 0.7880 0.8257 0.046 Uiso 1 1 calc GR . . . .
C14 C 0.51079(18) 0.72768(17) 1.12826(17) 0.0307(3) Uani 1 1 d . . . . .
H14A H 0.5481 0.7361 1.0509 0.046 Uiso 1 1 calc GR . . . .
H14B H 0.5455 0.6471 1.1602 0.046 Uiso 1 1 calc GR . . . .
H14C H 0.5603 0.8180 1.2087 0.046 Uiso 1 1 calc GR . . . .
C15 C 0.21506(19) 0.45961(17) 1.15407(15) 0.0281(3) Uani 1 1 d . . . . .
H15A H 0.1067 0.4481 1.1632 0.042 Uiso 1 1 calc GR . . . .
H15B H 0.2869 0.5544 1.2184 0.042 Uiso 1 1 calc GR . . . .
H15C H 0.2667 0.3829 1.1797 0.042 Uiso 1 1 calc GR . . . .
C16 C -0.35130(18) -0.06631(15) 0.61546(16) 0.0273(3) Uani 1 1 d . . . . .
C17 C -0.41926(19) -0.12530(17) 0.70890(18) 0.0327(4) Uani 1 1 d . . . . .
H17 H -0.4898 -0.2204 0.6677 0.039 Uiso 1 1 calc R . . . .
C18 C -0.3905(2) -0.05765(19) 0.84396(19) 0.0348(4) Uani 1 1 d . . . . .
H18A H -0.3207 0.0376 0.8896 0.042 Uiso 1 1 calc R . . . .
H18B H -0.4397 -0.1042 0.8956 0.042 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'
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
C2 O1 C12 117.18(12) . .
C3 O2 C13 113.04(11) . .
C4 O3 C14 112.64(10) . .
C8 O4 C11 102.80(10) . .
C2 C1 C6 120.19(13) . .
C2 C1 C11 120.61(12) . .
C6 C1 C11 119.20(12) . .
O1 C2 C1 117.52(12) . .
O1 C2 C3 122.43(13) . .
C3 C2 C1 119.99(13) . .
O2 C3 C2 121.54(12) . .
O2 C3 C4 119.25(12) . .
C2 C3 C4 119.18(13) . .
O3 C4 C3 118.21(13) . .
O3 C4 C5 119.98(12) . .
C5 C4 C3 121.76(13) . .
C4 C5 C6 118.29(12) . .
C4 C5 C15 120.39(13) . .
C6 C5 C15 121.32(13) . .
C1 C6 C5 120.49(13) . .
C1 C6 C7 118.71(12) . .
C5 C6 C7 120.77(12) . .
C6 C7 H7A 109.2 . .
C6 C7 H7B 109.2 . .
C6 C7 C8 111.93(11) . .
H7A C7 H7B 107.9 . .
C8 C7 H7A 109.2 . .
C8 C7 H7B 109.2 . .
O4 C8 C7 108.70(11) . .
O4 C8 H8 110.1 . .
O4 C8 C9 104.30(11) . .
C7 C8 H8 110.1 . .
C7 C8 C9 113.31(11) . .
C9 C8 H8 110.1 . .
C8 C9 H9 109.9 . .
C10 C9 C8 103.09(11) . .
C10 C9 H9 109.9 . .
C16 C9 C8 110.21(11) . .
C16 C9 H9 109.9 . .
C16 C9 C10 113.61(12) . .
C9 C10 H10A 111.2 . .
C9 C10 H10B 111.2 . .
H10A C10 H10B 109.1 . .
C11 C10 C9 102.80(11) . .
C11 C10 H10A 111.2 . .
C11 C10 H10B 111.2 . .
O4 C11 C1 109.02(11) . .
O4 C11 C10 102.85(11) . .
O4 C11 H11 110.8 . .
C1 C11 C10 112.22(11) . .
C1 C11 H11 110.8 . .
C10 C11 H11 110.8 . .
O1 C12 H12A 109.5 . .
O1 C12 H12B 109.5 . .
O1 C12 H12C 109.5 . .
H12A C12 H12B 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
O2 C13 H13A 109.5 . .
O2 C13 H13B 109.5 . .
O2 C13 H13C 109.5 . .
H13A C13 H13B 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
O3 C14 H14A 109.5 . .
O3 C14 H14B 109.5 . .
O3 C14 H14C 109.5 . .
H14A C14 H14B 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C5 C15 H15A 109.5 . .
C5 C15 H15B 109.5 . .
C5 C15 H15C 109.5 . .
H15A C15 H15B 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
O5 C16 C9 122.43(14) . .
O5 C16 C17 119.05(14) . .
C17 C16 C9 118.51(13) . .
C16 C17 H17 117.1 . .
C18 C17 C16 125.87(14) . .
C18 C17 H17 117.1 . .
C17 C18 H18A 120.0 . .
C17 C18 H18B 120.0 . .
H18A C18 H18B 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.3722(17) .
O1 C12 1.420(2) .
O2 C3 1.3805(17) .
O2 C13 1.4309(18) .
O3 C4 1.3807(17) .
O3 C14 1.4400(17) .
O4 C8 1.4309(16) .
O4 C11 1.4410(17) .
O5 C16 1.217(2) .
C1 C2 1.394(2) .
C1 C6 1.3972(19) .
C1 C11 1.5103(19) .
C2 C3 1.393(2) .
C3 C4 1.397(2) .
C4 C5 1.394(2) .
C5 C6 1.401(2) .
C5 C15 1.5086(19) .
C6 C7 1.5155(19) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C7 C8 1.525(2) .
C8 H8 1.0000 .
C8 C9 1.5620(18) .
C9 H9 1.0000 .
C9 C10 1.5391(19) .
C9 C16 1.5195(19) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C10 C11 1.5298(19) .
C11 H11 1.0000 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 C17 1.483(2) .
C17 H17 0.9500 .
C17 C18 1.318(2) .
C18 H18A 0.9500 .
C18 H18B 0.9500 .
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
O1 C2 C3 O2 -3.6(2) . . . .
O1 C2 C3 C4 178.53(11) . . . .
O2 C3 C4 O3 1.97(18) . . . .
O2 C3 C4 C5 179.59(11) . . . .
O3 C4 C5 C6 177.94(11) . . . .
O3 C4 C5 C15 -2.28(19) . . . .
O4 C8 C9 C10 -20.35(13) . . . .
O4 C8 C9 C16 101.24(12) . . . .
O5 C16 C17 C18 -174.21(16) . . . .
C1 C2 C3 O2 179.55(11) . . . .
C1 C2 C3 C4 1.6(2) . . . .
C1 C6 C7 C8 -4.10(17) . . . .
C2 C1 C6 C5 -3.4(2) . . . .
C2 C1 C6 C7 178.91(11) . . . .
C2 C1 C11 O4 148.32(12) . . . .
C2 C1 C11 C10 -98.42(14) . . . .
C2 C3 C4 O3 179.93(11) . . . .
C2 C3 C4 C5 -2.4(2) . . . .
C3 C4 C5 C6 0.4(2) . . . .
C3 C4 C5 C15 -179.87(12) . . . .
C4 C5 C6 C1 2.54(19) . . . .
C4 C5 C6 C7 -179.77(11) . . . .
C5 C6 C7 C8 178.18(11) . . . .
C6 C1 C2 O1 -175.83(11) . . . .
C6 C1 C2 C3 1.2(2) . . . .
C6 C1 C11 O4 -30.61(16) . . . .
C6 C1 C11 C10 82.65(15) . . . .
C6 C7 C8 O4 43.88(14) . . . .
C6 C7 C8 C9 -71.57(14) . . . .
C7 C8 C9 C10 97.69(13) . . . .
C7 C8 C9 C16 -140.73(12) . . . .
C8 O4 C11 C1 69.29(12) . . . .
C8 O4 C11 C10 -49.98(12) . . . .
C8 C9 C10 C11 -9.00(13) . . . .
C8 C9 C16 O5 -106.98(16) . . . .
C8 C9 C16 C17 71.45(16) . . . .
C9 C10 C11 O4 35.41(13) . . . .
C9 C10 C11 C1 -81.61(13) . . . .
C9 C16 C17 C18 7.3(2) . . . .
C10 C9 C16 O5 8.1(2) . . . .
C10 C9 C16 C17 -173.45(13) . . . .
C11 O4 C8 C7 -77.45(12) . . . .
C11 O4 C8 C9 43.70(12) . . . .
C11 C1 C2 O1 5.26(19) . . . .
C11 C1 C2 C3 -177.70(12) . . . .
C11 C1 C6 C5 175.58(11) . . . .
C11 C1 C6 C7 -2.15(18) . . . .
C12 O1 C2 C1 -124.39(15) . . . .
C12 O1 C2 C3 58.65(19) . . . .
C13 O2 C3 C2 84.21(16) . . . .
C13 O2 C3 C4 -97.88(15) . . . .
C14 O3 C4 C3 -83.05(15) . . . .
C14 O3 C4 C5 99.28(15) . . . .
C15 C5 C6 C1 -177.23(11) . . . .
C15 C5 C6 C7 0.46(19) . . . .
C16 C9 C10 C11 -128.25(12) . . . .
