#------------------------------------------------------------------------------
#$Date: 2017-12-21 02:04:32 +0200 (Thu, 21 Dec 2017) $
#$Revision: 204417 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/85/1548510.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_1548510
loop_
_publ_author_name
'Cao, Jia-Qing'
'Tian, Hai-Yan'
'Li, Man-Mei'
'Zhang, Wei'
'Wang, Ying'
'Wang, Lei'
'Ye, Wen-Cai'
_publ_section_title
;
 Rearranged Phloroglucinol-Monoterpenoid Adducts from Callistemon rigidus
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.7b00606
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H30 O5'
_chemical_formula_weight         374.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/4
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.52430(10)
_cell_length_b                   12.3365(2)
_cell_length_c                   22.0854(2)
_cell_measurement_reflns_used    14811
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      1.00000
_cell_measurement_theta_min      0.29173
_cell_volume                     2050.04(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 5.2684
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            19324
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         73.918
_diffrn_reflns_theta_min         4.003
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29173
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       blocks
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 1661 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(7)
_refine_ls_extinction_coef       0.0020(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         4084
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0518P)²+0.2194P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0812
_reflns_Friedel_coverage         0.729
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                4016
_reflns_number_total             4084
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np7b00606_si_003.cif
_cod_data_source_block           exp_595
_cod_database_code               1548510
_shelx_shelxl_version_number     2016/4
_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
O1 O 0.49532(17) 0.58936(11) 0.62131(5) 0.0286(3) Uani 1 1 d . .
H1 H 0.462267 0.622076 0.591015 0.043 Uiso 1 1 calc R U
O2 O 0.29971(17) 0.71076(12) 0.55887(5) 0.0349(3) Uani 1 1 d . .
O3 O 0.44150(16) 0.59854(9) 0.83575(5) 0.0246(3) Uani 1 1 d . .
O4 O 0.11417(17) 1.01085(9) 0.79978(5) 0.0255(3) Uani 1 1 d . .
O5 O 0.07217(14) 0.82051(9) 0.72400(5) 0.0209(2) Uani 1 1 d . .
C1 C 0.3939(2) 0.63142(12) 0.77929(7) 0.0191(3) Uani 1 1 d . .
C2 C 0.4725(2) 0.59275(13) 0.72641(7) 0.0207(3) Uani 1 1 d . .
H2 H 0.562653 0.541306 0.728421 0.025 Uiso 1 1 calc R U
C3 C 0.4153(2) 0.63156(13) 0.67060(7) 0.0212(3) Uani 1 1 d . .
C4 C 0.2785(2) 0.71112(13) 0.66473(7) 0.0196(3) Uani 1 1 d . .
C6 C -0.0330(2) 0.93662(13) 0.80224(7) 0.0209(3) Uani 1 1 d . .
H6 H -0.147359 0.964998 0.788143 0.025 Uiso 1 1 calc R U
C7 C 0.0374(2) 0.98525(13) 0.85807(7) 0.0218(3) Uani 1 1 d . .
H7 H -0.035743 1.042034 0.876570 0.026 Uiso 1 1 calc R U
C8 C 0.1525(2) 0.92052(13) 0.90081(7) 0.0211(3) Uani 1 1 d . .
H8 H 0.234123 0.971434 0.920466 0.025 Uiso 1 1 calc R U
C9 C 0.2655(2) 0.84097(13) 0.86400(7) 0.0209(3) Uani 1 1 d . .
H9A H 0.338229 0.798570 0.891466 0.025 Uiso 1 1 calc R U
H9B H 0.344625 0.881589 0.837769 0.025 Uiso 1 1 calc R U
C1' C 0.2263(2) 0.74938(14) 0.60440(7) 0.0233(3) Uani 1 1 d . .
C2' C 0.0798(2) 0.83193(14) 0.59574(7) 0.0221(3) Uani 1 1 d . .
H2' H 0.086397 0.885283 0.628537 0.026 Uiso 1 1 calc R U
C3' C 0.1017(3) 0.89081(16) 0.53516(7) 0.0304(4) Uani 1 1 d . .
H3'1 H 0.213718 0.928014 0.534546 0.046 Uiso 1 1 calc R U
H3'2 H 0.007076 0.942279 0.530224 0.046 Uiso 1 1 calc R U
H3'3 H 0.097910 0.839056 0.502722 0.046 Uiso 1 1 calc R U
C4' C -0.0989(2) 0.77154(13) 0.60016(7) 0.0231(3) Uani 1 1 d . .
H4'1 H -0.112411 0.725028 0.565048 0.028 Uiso 1 1 calc R U
H4'2 H -0.097959 0.725745 0.635861 0.028 Uiso 1 1 calc R U
C5' C -0.2560(3) 0.84775(17) 0.60364(10) 0.0378(5) Uani 1 1 d . .
H5'1 H -0.240958 0.896091 0.637316 0.057 Uiso 1 1 calc R U
H5'2 H -0.363135 0.806559 0.608947 0.057 Uiso 1 1 calc R U
H5'3 H -0.263675 0.888983 0.566869 0.057 Uiso 1 1 calc R U
C6' C -0.1664(2) 0.75548(14) 0.78627(8) 0.0260(4) Uani 1 1 d . .
H6'1 H -0.248814 0.788327 0.758613 0.039 Uiso 1 1 calc R U
H6'2 H -0.216800 0.754777 0.826203 0.039 Uiso 1 1 calc R U
H6'3 H -0.142260 0.682491 0.773636 0.039 Uiso 1 1 calc R U
C7' C 0.0378(2) 0.86852(13) 0.95109(7) 0.0234(3) Uani 1 1 d . .
H7' H -0.041393 0.815355 0.932149 0.028 Uiso 1 1 calc R U
C8' C -0.0775(3) 0.95311(14) 0.98358(8) 0.0294(4) Uani 1 1 d . .
H8'1 H -0.128321 0.921486 1.019333 0.044 Uiso 1 1 calc R U
H8'2 H -0.170942 0.976574 0.957038 0.044 Uiso 1 1 calc R U
H8'3 H -0.005442 1.014152 0.994703 0.044 Uiso 1 1 calc R U
C9' C 0.1537(3) 0.80911(16) 0.99722(8) 0.0348(4) Uani 1 1 d . .
H9'1 H 0.240120 0.858362 1.013549 0.052 Uiso 1 1 calc R U
H9'2 H 0.213472 0.749866 0.977726 0.052 Uiso 1 1 calc R U
H9'3 H 0.080437 0.781801 1.029360 0.052 Uiso 1 1 calc R U
C10' C 0.5772(2) 0.51732(14) 0.84024(8) 0.0277(4) Uani 1 1 d . .
H10A H 0.540436 0.453549 0.818703 0.042 Uiso 1 1 calc R U
H10B H 0.596449 0.499590 0.882050 0.042 Uiso 1 1 calc R U
H10C H 0.685486 0.544450 0.822971 0.042 Uiso 1 1 calc R U
C4A C 0.20441(19) 0.74568(12) 0.72019(7) 0.0184(3) Uani 1 1 d . .
C5A C 0.0052(2) 0.82001(13) 0.78683(6) 0.0189(3) Uani 1 1 d . .
C9A C 0.15239(19) 0.76370(12) 0.82516(7) 0.0181(3) Uani 1 1 d . .
H9A1 H 0.097622 0.709026 0.851393 0.022 Uiso 1 1 calc R U
C9B C 0.2571(2) 0.70764(12) 0.77602(7) 0.0184(3) Uani 1 1 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'
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
C1 O3 C10' 117.36(13)
C6 O4 C7 61.29(10)
C4A O5 C5A 107.77(11)
O3 C1 C2 123.71(14)
O3 C1 C9B 116.28(13)
C2 C1 C9B 120.01(14)
C3 C2 C1 119.59(14)
O1 C3 C2 116.40(14)
O1 C3 C4 120.91(14)
C2 C3 C4 122.69(14)
C4A C4 C3 114.42(14)
C4A C4 C1' 125.81(14)
C3 C4 C1' 119.77(14)
O4 C6 C7 59.63(10)
O4 C6 C5A 116.95(13)
C7 C6 C5A 120.72(13)
O4 C7 C6 59.08(10)
O4 C7 C8 116.29(13)
C6 C7 C8 121.01(14)
C7 C8 C9 109.00(12)
C7 C8 C7' 110.40(13)
C9 C8 C7' 115.17(13)
C8 C9 C9A 112.67(13)
O2 C1' C4 119.51(15)
O2 C1' C2' 118.67(14)
C4 C1' C2' 121.78(13)
C1' C2' C3' 110.60(14)
C1' C2' C4' 107.60(13)
C3' C2' C4' 112.24(13)
C5' C4' C2' 112.64(14)
C9' C7' C8' 109.69(14)
C9' C7' C8 111.06(14)
C8' C7' C8 111.68(13)
O5 C4A C9B 112.71(13)
O5 C4A C4 123.21(14)
C9B C4A C4 124.07(14)
O5 C5A C6 105.87(12)
O5 C5A C6' 106.57(12)
C6 C5A C6' 109.93(13)
O5 C5A C9A 105.66(11)
C6 C5A C9A 116.03(13)
C6' C5A C9A 112.06(13)
C9B C9A C9 113.33(13)
C9B C9A C5A 100.64(12)
C9 C9A C5A 114.83(13)
C4A C9B C1 119.19(14)
C4A C9B C9A 109.73(13)
C1 C9B C9A 131.03(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.3485(19)
O2 C1' 1.242(2)
O3 C1 1.3592(18)
O3 C10' 1.4338(19)
O4 C6 1.4377(19)
O4 C7 1.4459(19)
O5 C4A 1.3599(18)
O5 C5A 1.4762(17)
C1 C2 1.393(2)
C1 C9B 1.396(2)
C2 C3 1.390(2)
C3 C4 1.428(2)
C4 C4A 1.411(2)
C4 C1' 1.467(2)
C6 C7 1.470(2)
C6 C5A 1.506(2)
C7 C8 1.510(2)
C8 C9 1.532(2)
C8 C7' 1.546(2)
C9 C9A 1.539(2)
C1' C2' 1.513(2)
C2' C3' 1.531(2)
C2' C4' 1.541(2)
C4' C5' 1.512(2)
C6' C5A 1.517(2)
C7' C9' 1.528(2)
C7' C8' 1.535(2)
C4A C9B 1.378(2)
C5A C9A 1.558(2)
C9A C9B 1.509(2)
