#------------------------------------------------------------------------------
#$Date: 2023-06-05 06:52:54 +0200 (Mon 05 de Jun de 2023) $
#$Revision: 284320 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/93/7159336.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_7159336
loop_
_publ_author_name
'Huang, Jia-Hua'
'Lv, Jian-Ming'
'Xie, Yan-Feng'
'Zhao, Huan'
'Xiao, Liang-Yan'
'Dai, Ping'
'Qin, Sheng-Ying'
'Hu, Dan'
'Gao, Hao'
'Yao, Xin-Sheng'
_publ_section_title
;
 Isolation of new compounds related to xyloketals biosynthesis implies an
 alternative pathway for furan-fused-chromene formation.
;
_journal_issue                   20
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4309
_journal_page_last               4318
_journal_paper_doi               10.1039/d3ob00426k
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C21 H28 O4'
_chemical_formula_sum            'C21 H28 O4'
_chemical_formula_weight         344.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-03-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-03-04 deposited with the CCDC.	2023-05-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.143(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6389(2)
_cell_length_b                   11.9203(2)
_cell_length_c                   12.9914(3)
_cell_measurement_reflns_used    7769
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.6950
_cell_measurement_theta_min      3.6820
_cell_volume                     1859.97(6)
_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_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -96.00  -2.00   1.00    1.00    --  -41.11 125.00  90.00   94
  2  ω   -115.00 -17.00   1.00    1.00    --  -41.11 -38.00 -30.00   98
  3  ω      9.00 117.00   1.00    1.00    --   41.11  77.00  90.00  108
  4  ω     17.00 115.00   1.00    1.00    --   41.11  38.00 -90.00   98
  5  ω      1.00  82.00   1.00    1.00    --   41.11 -99.00 -30.00   81
  6  ω     31.00 136.00   1.00    1.85    --  107.58 -30.00 150.00  105
  7  ω     34.00 122.00   1.00    1.85    --  107.58-125.00 -30.00   88
  8  ω     31.00 136.00   1.00    1.85    --  107.58 -30.00 -30.00  105
  9  ω     82.00 178.00   1.00    1.85    --  107.58  45.00 -30.00   96
 10  ω     82.00 178.00   1.00    1.85    --  107.58  45.00 150.00   96
 11  ω     79.00 178.00   1.00    1.85    --  107.58  30.00-150.00   99
 12  ω     25.00 110.00   1.00    1.85    --  107.58 -95.00  90.00   85
 13  ω     25.00  89.00   1.00    1.85    --  107.58 -95.00  30.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0776191000
_diffrn_orient_matrix_UB_12      0.1028371000
_diffrn_orient_matrix_UB_13      -0.0196110000
_diffrn_orient_matrix_UB_21      -0.1012750000
_diffrn_orient_matrix_UB_22      -0.0767604000
_diffrn_orient_matrix_UB_23      -0.0489885000
_diffrn_orient_matrix_UB_31      -0.0132447000
_diffrn_orient_matrix_UB_32      -0.0154012000
_diffrn_orient_matrix_UB_33      0.1130608000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12983
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.801
_diffrn_reflns_theta_min         3.680
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3674
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0400
_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)+(0.0510P)²+0.6239P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1055
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3298
_reflns_number_total             3674
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00426k2.cif
_cod_data_source_block           c70m-2-4-1
_cod_depositor_comments
'Adding full bibliography for 7159333--7159336.cif.'
_cod_original_cell_volume        1859.97(7)
_cod_database_code               7159336
_shelx_shelxl_version_number     2014/7
_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   0.930
_shelx_estimated_absorpt_t_min   0.912
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C6'(H6'), C6(H6), C5(H5), C5'(H5')
2.b Secondary CH2 refined with riding coordinates:
 C7'(H7'A,H7'B), C7(H7A,H7B), C4(H4A,H4B), C4'(H4'A,H4'B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C10'(H10A,H10B,H10C), C11'(H11A,H11B,H11C), C11(H11D,
 H11E,H11F), C10(H10D,H10E,H10F)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.411
_oxdiff_exptl_absorpt_empirical_full_min 0.403
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_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 -0.00435(7) 0.19692(7) 0.15328(7) 0.0278(2) Uani 1 1 d . . . . .
O1 O -0.32444(8) 0.06411(7) 0.21449(8) 0.0320(2) Uani 1 1 d . . . . .
O3' O 0.16829(7) 0.23073(8) 0.14282(7) 0.0299(2) Uani 1 1 d . . . . .
O3 O -0.43836(8) -0.04112(9) 0.27877(8) 0.0387(2) Uani 1 1 d . . . . .
C8' C -0.08132(10) 0.31128(10) 0.26941(10) 0.0227(3) Uani 1 1 d . . . . .
C13 C -0.16887(10) 0.14034(10) 0.18266(10) 0.0232(3) Uani 1 1 d . . . . .
H13 H -0.1715 0.0808 0.1357 0.028 Uiso 1 1 calc R . . . .
C12 C -0.16626(10) 0.32282(10) 0.31716(10) 0.0225(2) Uani 1 1 d . . . . .
C9' C -0.08435(10) 0.21912(10) 0.20224(9) 0.0221(2) Uani 1 1 d . . . . .
C8 C -0.25039(10) 0.24193(10) 0.30148(10) 0.0229(3) Uani 1 1 d . . . . .
C6' C 0.10773(10) 0.35257(10) 0.25225(10) 0.0245(3) Uani 1 1 d . . . . .
H6' H 0.1515 0.4171 0.2420 0.029 Uiso 1 1 calc R . . . .
C9 C -0.24953(10) 0.15121(10) 0.23388(10) 0.0234(3) Uani 1 1 d . . . . .
C7' C 0.01153(10) 0.39616(10) 0.28806(11) 0.0281(3) Uani 1 1 d . . . . .
H7'A H 0.0388 0.4149 0.3645 0.034 Uiso 1 1 calc R . . . .
H7'B H -0.0175 0.4642 0.2483 0.034 Uiso 1 1 calc R . . . .
C1' C 0.07177(10) 0.28605(10) 0.14740(10) 0.0252(3) Uani 1 1 d . . . . .
C14 C -0.16484(11) 0.42334(10) 0.38846(11) 0.0290(3) Uani 1 1 d . . . . .
H14A H -0.1179 0.4078 0.4608 0.044 Uiso 1 1 calc GR . . . .
H14B H -0.2391 0.4387 0.3893 0.044 Uiso 1 1 calc GR . . . .
H14C H -0.1366 0.4873 0.3606 0.044 Uiso 1 1 calc GR . . . .
C6 C -0.39275(10) 0.13405(11) 0.35841(10) 0.0263(3) Uani 1 1 d . . . . .
H6 H -0.4615 0.1444 0.3770 0.032 Uiso 1 1 calc R . . . .
C7 C -0.34042(11) 0.24870(11) 0.35553(11) 0.0291(3) Uani 1 1 d . . . . .
H7A H -0.3975 0.3011 0.3162 0.035 Uiso 1 1 calc R . . . .
H7B H -0.3086 0.2765 0.4289 0.035 Uiso 1 1 calc R . . . .
C4 C -0.37089(12) -0.06268(12) 0.38932(12) 0.0358(3) Uani 1 1 d . . . . .
H4A H -0.3130 -0.1167 0.3909 0.043 Uiso 1 1 calc R . . . .
H4B H -0.4165 -0.0926 0.4307 0.043 Uiso 1 1 calc R . . . .
C2 C -0.42007(10) 0.06944(11) 0.25241(11) 0.0284(3) Uani 1 1 d . . . . .
C10' C 0.02137(12) 0.35108(12) 0.04441(11) 0.0351(3) Uani 1 1 d . . . . .
H10A H 0.0090 0.3017 -0.0166 0.053 Uiso 1 1 calc GR . . . .
H10B H 0.0712 0.4101 0.0393 0.053 Uiso 1 1 calc GR . . . .
H10C H -0.0483 0.3829 0.0448 0.053 Uiso 1 1 calc GR . . . .
C4' C 0.24202(11) 0.21583(12) 0.25169(12) 0.0335(3) Uani 1 1 d . . . . .
H4'A H 0.3132 0.2512 0.2596 0.040 Uiso 1 1 calc R . . . .
H4'B H 0.2546 0.1366 0.2679 0.040 Uiso 1 1 calc R . . . .
C5 C -0.31912(11) 0.04940(11) 0.43734(11) 0.0300(3) Uani 1 1 d . . . . .
H5 H -0.2437 0.0538 0.4317 0.036 Uiso 1 1 calc R . . . .
C5' C 0.18689(11) 0.26973(11) 0.32852(11) 0.0293(3) Uani 1 1 d . . . . .
H5' H 0.1435 0.2131 0.3524 0.035 Uiso 1 1 calc R . . . .
C11' C 0.27004(12) 0.32340(14) 0.42690(12) 0.0395(3) Uani 1 1 d . . . . .
H11A H 0.3100 0.3815 0.4037 0.059 Uiso 1 1 calc GR . . . .
H11B H 0.3215 0.2675 0.4664 0.059 Uiso 1 1 calc GR . . . .
H11C H 0.2311 0.3550 0.4728 0.059 Uiso 1 1 calc GR . . . .
C11 C -0.31238(15) 0.06583(14) 0.55509(12) 0.0464(4) Uani 1 1 d . . . . .
H11D H -0.2839 0.1393 0.5784 0.070 Uiso 1 1 calc GR . . . .
H11E H -0.2637 0.0104 0.5989 0.070 Uiso 1 1 calc GR . . . .
H11F H -0.3853 0.0582 0.5624 0.070 Uiso 1 1 calc GR . . . .
C10 C -0.51761(13) 0.10921(17) 0.16014(13) 0.0514(4) Uani 1 1 d . . . . .
H10D H -0.5044 0.1846 0.1413 0.077 Uiso 1 1 calc GR . . . .
H10E H -0.5838 0.1072 0.1815 0.077 Uiso 1 1 calc GR . . . .
H10F H -0.5270 0.0612 0.0986 0.077 Uiso 1 1 calc GR . . . .
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
_geom_angle_publ_flag
C9' O1' C1' 118.53(9) . . ?
C9 O1 C2 120.47(9) . . ?
C1' O3' C4' 108.72(9) . . ?
C2 O3 C4 108.61(10) . . ?
C12 C8' C7' 121.75(10) . . ?
C9' C8' C12 118.52(11) . . ?
C9' C8' C7' 119.73(11) . . ?
C9' C13 C9 119.27(11) . . ?
C8' C12 C14 118.93(11) . . ?
C8 C12 C8' 121.19(11) . . ?
C8 C12 C14 119.86(11) . . ?
O1' C9' C8' 123.96(11) . . ?
O1' C9' C13 114.83(10) . . ?
C13 C9' C8' 121.19(11) . . ?
C12 C8 C7 122.77(11) . . ?
C9 C8 C12 118.04(11) . . ?
C9 C8 C7 119.19(11) . . ?
C7' C6' C5' 116.49(11) . . ?
C1' C6' C7' 114.08(10) . . ?
C1' C6' C5' 101.34(10) . . ?
O1 C9 C13 114.14(10) . . ?
O1 C9 C8 124.11(11) . . ?
C13 C9 C8 121.72(11) . . ?
C8' C7' C6' 112.14(10) . . ?
O1' C1' C6' 110.69(9) . . ?
O1' C1' C10' 108.65(10) . . ?
O3' C1' O1' 104.92(9) . . ?
O3' C1' C6' 105.19(10) . . ?
O3' C1' C10' 109.69(10) . . ?
C10' C1' C6' 117.00(11) . . ?
C7 C6 C5 115.46(10) . . ?
C2 C6 C7 114.20(11) . . ?
C2 C6 C5 101.08(10) . . ?
C8 C7 C6 110.99(10) . . ?
O3 C4 C5 107.11(11) . . ?
O1 C2 C6 110.71(10) . . ?
O1 C2 C10 107.93(11) . . ?
O3 C2 O1 105.20(10) . . ?
O3 C2 C6 105.29(11) . . ?
O3 C2 C10 109.59(12) . . ?
C10 C2 C6 117.44(12) . . ?
O3' C4' C5' 107.61(10) . . ?
C6 C5 C4 102.04(11) . . ?
C11 C5 C6 114.95(12) . . ?
C11 C5 C4 113.93(12) . . ?
C4' C5' C6' 100.83(10) . . ?
C11' C5' C6' 114.48(11) . . ?
C11' C5' C4' 112.98(12) . . ?
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' 1.3776(14) . ?
O1' C1' 1.4512(14) . ?
O1 C9 1.3746(14) . ?
O1 C2 1.4416(14) . ?
O3' C1' 1.4041(14) . ?
O3' C4' 1.4420(17) . ?
O3 C4 1.4467(18) . ?
O3 C2 1.3989(16) . ?
C8' C12 1.4039(17) . ?
C8' C9' 1.3960(17) . ?
C8' C7' 1.5108(16) . ?
C13 C9' 1.3851(16) . ?
C13 C9 1.3861(16) . ?
C12 C8 1.4026(17) . ?
C12 C14 1.5112(16) . ?
C8 C9 1.3952(17) . ?
C8 C7 1.5139(16) . ?
C6' C7' 1.5221(16) . ?
C6' C1' 1.5183(17) . ?
C6' C5' 1.5298(17) . ?
C1' C10' 1.5054(18) . ?
C6 C7 1.5238(17) . ?
C6 C2 1.5207(18) . ?
C6 C5 1.5302(18) . ?
C4 C5 1.5323(19) . ?
C2 C10 1.5037(19) . ?
C4' C5' 1.5257(19) . ?
C5 C11 1.518(2) . ?
C5' C11' 1.5201(19) . ?
