#------------------------------------------------------------------------------
#$Date: 2020-02-29 01:42:31 +0200 (Sat, 29 Feb 2020) $
#$Revision: 248532 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/42/4134265.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_4134265
loop_
_publ_author_name
'Gao, Jianhong'
'Rao, Peirong'
'Xu, Kaixiang'
'Wang, Shuaifeng'
'Wu, Yufei'
'Ding, Hanfeng'
_publ_section_title
;
 Total Synthesis of (-)-Rhodomollanol A.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c00308
_journal_year                    2020
_chemical_formula_moiety         'C20 H28 O5'
_chemical_formula_sum            'C20 H28 O5'
_chemical_formula_weight         348.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                99.192(19)
_cell_angle_beta                 101.842(19)
_cell_angle_gamma                99.459(17)
_cell_formula_units_Z            2
_cell_length_a                   8.585(3)
_cell_length_b                   9.649(3)
_cell_length_c                   10.848(4)
_cell_measurement_reflns_used    7208
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.11
_cell_measurement_theta_min      2.48
_cell_volume                     849.9(5)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10429
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.072
_diffrn_reflns_theta_min         2.476
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7134
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1176 before and 0.0329 after correction.
The Ratio of minimum to maximum transmission is 0.9569.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3709
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0376
_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)+(0.0476P)²+0.3634P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.0978
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3450
_reflns_number_total             3709
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c00308_si_005.cif
_cod_data_source_block           191210_gjh_rhodomollanol_0m
_cod_database_code               4134265
_shelx_shelxl_version_number     2016/6
_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.
;
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.954
_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, All C(H,H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2A), C5(H5A), C7(H7), C10(H10), C11(H11), C14(H14), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O5(H5)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 -0.06807(10) 0.45741(9) 0.86931(8) 0.01945(18) Uani 1 1 d . . . . .
O2 O 0.26645(10) 0.52060(8) 0.94268(7) 0.01497(17) Uani 1 1 d . . . . .
O3 O 0.46594(10) 0.32878(8) 0.84932(8) 0.01893(18) Uani 1 1 d . . . . .
H3 H 0.534187 0.380807 0.913628 0.028 Uiso 1 1 calc GR . . . .
O4 O 0.18245(10) 0.64949(9) 0.57028(8) 0.01931(19) Uani 1 1 d . . . . .
O5 O 0.59640(12) 1.07115(9) 0.79107(10) 0.0297(2) Uani 1 1 d . . . . .
H5 H 0.545139 1.133171 0.815464 0.045 Uiso 1 1 calc GR . . . .
C1 C -0.06202(13) 0.44255(12) 0.73446(10) 0.0166(2) Uani 1 1 d . . . . .
H1 H -0.160575 0.446390 0.668468 0.020 Uiso 1 1 calc R . . . .
C2 C -0.06019(14) 0.31894(12) 0.79571(11) 0.0184(2) Uani 1 1 d . . . . .
H2A H -0.157763 0.238848 0.771487 0.022 Uiso 1 1 calc R . . . .
C3 C 0.10878(14) 0.28491(11) 0.81794(11) 0.0171(2) Uani 1 1 d . . . . .
C4 C 0.22034(13) 0.43223(11) 0.81597(10) 0.0136(2) Uani 1 1 d . . . . .
C5 C 0.10565(13) 0.49372(11) 0.71416(10) 0.0140(2) Uani 1 1 d . . . . .
H5A H 0.105129 0.434665 0.629411 0.017 Uiso 1 1 calc R . . . .
C6 C 0.14689(13) 0.65239(12) 0.69614(10) 0.0157(2) Uani 1 1 d . . . . .
C7 C 0.30620(13) 0.73949(11) 0.78630(10) 0.0145(2) Uani 1 1 d . . . . .
H7 H 0.314656 0.724718 0.876419 0.017 Uiso 1 1 calc R . . . .
C8 C 0.43668(13) 0.67791(11) 0.72683(10) 0.0138(2) Uani 1 1 d . . . . .
C9 C 0.50021(13) 0.55972(11) 0.78879(10) 0.0149(2) Uani 1 1 d . . . . .
H9A H 0.545924 0.599943 0.881542 0.018 Uiso 1 1 calc R . . . .
H9B H 0.591300 0.536841 0.751671 0.018 Uiso 1 1 calc R . . . .
C10 C 0.38067(13) 0.41769(11) 0.77650(10) 0.0146(2) Uani 1 1 d . . . . .
H10 H 0.351556 0.368293 0.684090 0.018 Uiso 1 1 calc R . . . .
C11 C 0.34719(13) 0.62740(12) 0.58195(10) 0.0164(2) Uani 1 1 d . . . . .
H11 H 0.348102 0.524315 0.550760 0.020 Uiso 1 1 calc R . . . .
C12 C 0.43988(14) 0.72230(12) 0.51344(11) 0.0191(2) Uani 1 1 d . . . . .
H12 H 0.414350 0.713616 0.422733 0.023 Uiso 1 1 calc R . . . .
C13 C 0.56176(14) 0.82008(12) 0.59288(11) 0.0178(2) Uani 1 1 d . . . . .
C14 C 0.57361(13) 0.80940(11) 0.73267(11) 0.0157(2) Uani 1 1 d . . . . .
H14 H 0.682981 0.793732 0.773813 0.019 Uiso 1 1 calc R . . . .
C15 C 0.52726(14) 0.93625(12) 0.81495(11) 0.0186(2) Uani 1 1 d . . . . .
H15 H 0.568125 0.935035 0.907905 0.022 Uiso 1 1 calc R . . . .
C16 C 0.34231(14) 0.89929(11) 0.78172(11) 0.0179(2) Uani 1 1 d . . . . .
H16A H 0.296468 0.915737 0.695060 0.021 Uiso 1 1 calc R . . . .
H16B H 0.298191 0.956279 0.845571 0.021 Uiso 1 1 calc R . . . .
C17 C 0.10448(15) 0.16754(12) 0.70270(12) 0.0229(3) Uani 1 1 d . . . . .
H17A H 0.025381 0.081529 0.701965 0.034 Uiso 1 1 calc GR . . . .
H17B H 0.212463 0.144273 0.709841 0.034 Uiso 1 1 calc GR . . . .
H17C H 0.072849 0.201986 0.622807 0.034 Uiso 1 1 calc GR . . . .
C18 C 0.14990(15) 0.22940(13) 0.94311(12) 0.0224(2) Uani 1 1 d . . . . .
H18A H 0.146021 0.302605 1.015664 0.034 Uiso 1 1 calc GR . . . .
H18B H 0.259227 0.208276 0.955445 0.034 Uiso 1 1 calc GR . . . .
H18C H 0.070734 0.141846 0.938189 0.034 Uiso 1 1 calc GR . . . .
C19 C 0.00296(15) 0.72601(13) 0.69505(13) 0.0244(3) Uani 1 1 d . . . . .
H19A H 0.032205 0.823138 0.679489 0.037 Uiso 1 1 calc GR . . . .
H19B H -0.025965 0.731239 0.778252 0.037 Uiso 1 1 calc GR . . . .
H19C H -0.090017 0.671053 0.626712 0.037 Uiso 1 1 calc GR . . . .
C20 C 0.67810(15) 0.92619(13) 0.55119(12) 0.0239(3) Uani 1 1 d . . . . .
H20A H 0.678993 1.023398 0.595158 0.036 Uiso 1 1 calc GR . . . .
H20B H 0.643853 0.918605 0.458036 0.036 Uiso 1 1 calc GR . . . .
H20C H 0.787493 0.905937 0.573136 0.036 Uiso 1 1 calc GR . . . .
H2 H 0.181(2) 0.5198(19) 0.9738(17) 0.036 Uiso 1 1 d R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
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
C1 O1 C2 59.77(7) . . ?
C4 O2 H2 109.0(12) . . ?
C10 O3 H3 109.5 . . ?
C11 O4 C6 107.23(8) . . ?
C15 O5 H5 109.5 . . ?
O1 C1 H1 119.7 . . ?
O1 C1 C5 114.04(9) . . ?
C2 C1 O1 60.21(7) . . ?
C2 C1 H1 119.7 . . ?
C2 C1 C5 109.10(9) . . ?
C5 C1 H1 119.7 . . ?
O1 C2 H2A 119.6 . . ?
O1 C2 C3 114.19(9) . . ?
C1 C2 O1 60.02(7) . . ?
C1 C2 H2A 119.6 . . ?
C1 C2 C3 109.60(9) . . ?
C3 C2 H2A 119.6 . . ?
C2 C3 C4 102.80(9) . . ?
C2 C3 C17 105.83(9) . . ?
C2 C3 C18 110.93(10) . . ?
C17 C3 C4 111.85(9) . . ?
C18 C3 C4 114.97(9) . . ?
C18 C3 C17 109.89(10) . . ?
O2 C4 C3 109.44(9) . . ?
O2 C4 C5 113.77(8) . . ?
O2 C4 C10 106.00(9) . . ?
C5 C4 C3 102.13(9) . . ?
C10 C4 C3 114.54(9) . . ?
C10 C4 C5 111.18(9) . . ?
C1 C5 C4 103.33(9) . . ?
C1 C5 H5A 104.3 . . ?
C1 C5 C6 116.55(9) . . ?
C4 C5 H5A 104.3 . . ?
C6 C5 C4 122.18(9) . . ?
C6 C5 H5A 104.3 . . ?
O4 C6 C5 107.92(9) . . ?
O4 C6 C7 102.11(9) . . ?
O4 C6 C19 106.05(9) . . ?
C7 C6 C5 113.54(9) . . ?
C19 C6 C5 112.13(9) . . ?
C19 C6 C7 114.10(10) . . ?
C6 C7 H7 111.4 . . ?
C6 C7 C8 102.52(9) . . ?
C6 C7 C16 115.20(9) . . ?
C8 C7 H7 111.4 . . ?
C16 C7 H7 111.4 . . ?
C16 C7 C8 104.18(9) . . ?
C7 C8 C11 102.32(9) . . ?
C7 C8 C14 106.26(9) . . ?
C9 C8 C7 114.34(9) . . ?
C9 C8 C11 113.99(9) . . ?
C9 C8 C14 113.34(9) . . ?
C11 C8 C14 105.54(9) . . ?
C8 C9 H9A 107.7 . . ?
C8 C9 H9B 107.7 . . ?
C8 C9 C10 118.42(9) . . ?
H9A C9 H9B 107.1 . . ?
C10 C9 H9A 107.7 . . ?
C10 C9 H9B 107.7 . . ?
O3 C10 C4 111.07(9) . . ?
O3 C10 C9 107.83(9) . . ?
O3 C10 H10 107.3 . . ?
C4 C10 H10 107.3 . . ?
C9 C10 C4 115.57(9) . . ?
C9 C10 H10 107.3 . . ?
O4 C11 C8 107.06(8) . . ?
O4 C11 H11 111.0 . . ?
O4 C11 C12 111.72(9) . . ?
C8 C11 H11 111.0 . . ?
C12 C11 C8 104.90(9) . . ?
C12 C11 H11 111.0 . . ?
C11 C12 H12 123.5 . . ?
C13 C12 C11 113.02(10) . . ?
C13 C12 H12 123.5 . . ?
C12 C13 C14 112.05(10) . . ?
C12 C13 C20 124.76(11) . . ?
C20 C13 C14 123.17(10) . . ?
C8 C14 H14 111.2 . . ?
C13 C14 C8 104.35(9) . . ?
C13 C14 H14 111.2 . . ?
C13 C14 C15 114.62(9) . . ?
C15 C14 C8 103.93(9) . . ?
C15 C14 H14 111.2 . . ?
O5 C15 C14 111.94(9) . . ?
O5 C15 H15 108.7 . . ?
O5 C15 C16 115.08(10) . . ?
C14 C15 H15 108.7 . . ?
C16 C15 C14 103.52(9) . . ?
C16 C15 H15 108.7 . . ?
C7 C16 H16A 111.2 . . ?
C7 C16 H16B 111.2 . . ?
C15 C16 C7 102.65(9) . . ?
C15 C16 H16A 111.2 . . ?
C15 C16 H16B 111.2 . . ?
H16A C16 H16B 109.1 . . ?
C3 C17 H17A 109.5 . . ?
C3 C17 H17B 109.5 . . ?
C3 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C6 C19 H19A 109.5 . . ?
C6 C19 H19B 109.5 . . ?
C6 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C13 C20 H20A 109.5 . . ?
C13 C20 H20B 109.5 . . ?
C13 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
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 C1 1.4594(14) . ?
O1 C2 1.4623(14) . ?
O2 C4 1.4368(13) . ?
O2 H2 0.865(19) . ?
O3 H3 0.8400 . ?
O3 C10 1.4428(13) . ?
O4 C6 1.4560(14) . ?
O4 C11 1.4478(14) . ?
O5 H5 0.8400 . ?
O5 C15 1.4249(14) . ?
C1 H1 1.0000 . ?
C1 C2 1.4557(16) . ?
C1 C5 1.5151(16) . ?
C2 H2A 1.0000 . ?
C2 C3 1.5194(16) . ?
C3 C4 1.5840(15) . ?
C3 C17 1.5367(16) . ?
C3 C18 1.5340(16) . ?
C4 C5 1.5800(15) . ?
C4 C10 1.5440(15) . ?
C5 H5A 1.0000 . ?
C5 C6 1.5662(15) . ?
C6 C7 1.5310(16) . ?
C6 C19 1.5221(16) . ?
C7 H7 1.0000 . ?
C7 C8 1.5547(15) . ?
C7 C16 1.5329(15) . ?
C8 C9 1.5325(15) . ?
C8 C11 1.5603(16) . ?
C8 C14 1.5650(15) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5402(15) . ?
C10 H10 1.0000 . ?
C11 H11 1.0000 . ?
C11 C12 1.4982(16) . ?
C12 H12 0.9500 . ?
C12 C13 1.3316(17) . ?
C13 C14 1.5202(16) . ?
C13 C20 1.4991(16) . ?
C14 H14 1.0000 . ?
C14 C15 1.5523(15) . ?
C15 H15 1.0000 . ?
C15 C16 1.5219(17) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
