#------------------------------------------------------------------------------
#$Date: 2020-10-09 04:21:58 +0300 (Fri, 09 Oct 2020) $
#$Revision: 258262 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/93/1559307.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_1559307
loop_
_publ_author_name
'Chan, Hau Sun Sam'
'Thompson, Amber L.'
'Christensen, Kirsten E.'
'Burton, Jonathan W.'
_publ_section_title
;
 Forwards and backwards -- synthesis of Laurencia natural products using a
 biomimetic and retrobiomimetic strategy incorporating structural
 reassignment of laurefurenynes C--F
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC04120C
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H22 O4'
_chemical_formula_sum            'C13 H22 O4'
_chemical_formula_weight         242.32
_chemical_melting_point          ?
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             2018-04-23
_audit_creation_method           CRYSTALS_ver_14.61_build_6720
_audit_update_record
;
2020-05-21 deposited with the CCDC.	2020-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.005(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.9422(2)
_cell_length_b                   7.6020(2)
_cell_length_c                   14.7513(4)
_cell_measurement_reflns_used    7384
_cell_measurement_temperature    150
_cell_measurement_theta_max      76
_cell_measurement_theta_min      6
_cell_volume                     654.10(3)
_computing_cell_refinement
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_data_reduction
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.079
_diffrn_reflns_av_sigmaI/netI    0.0507
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13847
_diffrn_reflns_theta_full        75.161
_diffrn_reflns_theta_max         76.695
_diffrn_reflns_theta_min         6.112
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.60
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.41
_refine_diff_density_min         -0.37
_refine_ls_abs_structure_details
; 
 Parsons, Flack & Wagner (2013), 
 1157 Friedel Pairs 
;
_refine_ls_abs_structure_Flack   -0.01(9)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2730
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0575
_refine_ls_shift/su_max          0.0001375
_refine_ls_shift/su_mean         0.0000176
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.13P)² + 0.03P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1537
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1537
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              9
_reflns_limit_k_min              -9
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                2643
_reflns_number_total             2731
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   3.09
_oxford_diffrn_Wilson_scale      0.01
_oxford_refine_ls_r_factor_ref   0.0586
_oxford_refine_ls_scale          9.3(7)
_oxford_reflns_number_all        2730
_oxford_structure_analysis_title 6955
_cod_data_source_file            d0sc04120c2.cif
_cod_data_source_block           22
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'not measured' was changed
to '?' -- the value is undefined or not given.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21 '
_cod_database_code               1559307
_oxford_refine_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_hooft_y                  0.11(13)
_oxford_bijvoet_difference       -0.01(9)
_oxford_refined_flack_x          -0.15(19)
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C6 C 0.3921(4) 0.2241(3) 0.36917(14) 0.0414 1.0000 Uani . . . . . .
C7 C 0.3714(3) 0.3924(3) 0.31164(12) 0.0336 1.0000 Uani . . . . . .
C8 C 0.1236(3) 0.3749(3) 0.26072(12) 0.0349 1.0000 Uani . . . . . .
C9 C 0.1018(3) 0.1768(3) 0.24113(13) 0.0363 1.0000 Uani . . . . . .
C10 C 0.1171(3) 0.1187(3) 0.14301(13) 0.0330 1.0000 Uani . . . . . .
C11 C 0.3233(3) 0.1786(3) 0.10234(12) 0.0303 1.0000 Uani . . . . . .
C12 C 0.3520(3) 0.3766(3) 0.08709(12) 0.0316 1.0000 Uani . . . . . .
C13 C 0.5135(3) 0.4681(3) 0.16858(13) 0.0324 1.0000 Uani . . . . . .
C14 C 0.4688(4) 0.6658(3) 0.17617(18) 0.0436 1.0000 Uani . . . . . .
C15 C 0.6638(5) 0.7580(3) 0.2414(3) 0.0633 1.0000 Uani . . . . . .
O1 O 0.2833(3) 0.0941(2) 0.30520(10) 0.0413 1.0000 Uani . . . . . .
O2 O 0.5389(2) 0.3770(2) 0.25447(8) 0.0299 1.0000 Uani . . . . . .
O17 O 0.1300(2) 0.4581(2) 0.06156(10) 0.0378 1.0000 Uani D . . . . .
O16 O -0.0946(2) 0.1696(2) 0.08309(10) 0.0403 1.0000 Uani D . . . . .
C103 C 0.8782(11) 0.2979(9) 0.5530(5) 0.0501 0.490(11) Uani . . P 1 2 .
C3 C 0.8819(11) 0.3623(13) 0.5172(6) 0.0624 0.510(11) Uani . . P 1 1 .
C4 C 0.7001(9) 0.2619(7) 0.5023(3) 0.0459 0.510(11) Uani . . P 1 1 .
C104 C 0.7844(7) 0.3138(6) 0.4651(4) 0.0366 0.490(11) Uani . . P 1 2 .
C5 C 0.6324(4) 0.1643(3) 0.41192(15) 0.0479 1.0000 Uani . . . . . .
H61 H 0.2984 0.2351 0.4183 0.0502 1.0000 Uiso R . . . . .
H71 H 0.3968 0.4979 0.3488 0.0397 1.0000 Uiso R . . . . .
H82 H 0.0212 0.4080 0.3005 0.0415 1.0000 Uiso R . . . . .
H81 H 0.0896 0.4443 0.2050 0.0410 1.0000 Uiso R . . . . .
H91 H -0.0438 0.1327 0.2562 0.0435 1.0000 Uiso R . . . . .
H101 H 0.1217 -0.0081 0.1433 0.0398 1.0000 Uiso R . . . . .
H111 H 0.4588 0.1342 0.1425 0.0358 1.0000 Uiso R . . . . .
H112 H 0.3065 0.1267 0.0419 0.0350 1.0000 Uiso R . . . . .
H121 H 0.4287 0.3892 0.0360 0.0387 1.0000 Uiso R . . . . .
H131 H 0.6631 0.4597 0.1522 0.0386 1.0000 Uiso R . . . . .
H142 H 0.4520 0.7206 0.1164 0.0525 1.0000 Uiso R . . . . .
H141 H 0.3282 0.6830 0.1986 0.0512 1.0000 Uiso R . . . . .
H151 H 0.6241 0.8763 0.2518 0.0947 1.0000 Uiso R . . . . .
H152 H 0.7954 0.7560 0.2141 0.0947 1.0000 Uiso R . . . . .
H153 H 0.6964 0.6999 0.2997 0.0948 1.0000 Uiso R . . . . .
H1031 H 0.9581 0.3916 0.5846 0.0598 0.490(11) Uiso R . P 1 2 .
H1032 H 0.8642 0.1917 0.5831 0.0601 0.490(11) Uiso R . P 1 2 .
H32 H 0.9366 0.4090 0.5756 0.0749 0.510(11) Uiso R . P 1 1 .
H31 H 0.9615 0.3903 0.4703 0.0750 0.510(11) Uiso R . P 1 1 .
H41 H 0.6108 0.2506 0.5478 0.0548 0.510(11) Uiso R . P 1 1 .
H1041 H 0.8067 0.4190 0.4344 0.0435 0.490(11) Uiso R . P 1 2 .
H52 H 0.6266 0.0390 0.4246 0.0569 0.510(11) Uiso R . P 1 1 .
H54 H 0.7387 0.1839 0.3694 0.0568 0.510(11) Uiso R . P 1 1 .
H53 H 0.6225 0.0659 0.4533 0.0568 0.490(11) Uiso R . P 1 2 .
H51 H 0.7062 0.1249 0.3620 0.0564 0.490(11) Uiso R . P 1 2 .
H171 H 0.103(6) 0.522(4) 0.0172(17) 0.057(2) 1.0000 Uiso D . . . . .
H161 H -0.092(6) 0.272(3) 0.068(2) 0.060(2) 1.0000 Uiso D . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 . C6 . O1 . 103.51(15) yes
C7 . C6 . C5 . 116.87(19) yes
O1 . C6 . C5 . 109.70(18) yes
C7 . C6 . H61 . 109.7 no
O1 . C6 . H61 . 107.0 no
C5 . C6 . H61 . 109.5 no
C6 . C7 . C8 . 99.70(16) yes
C6 . C7 . O2 . 105.59(15) yes
C8 . C7 . O2 . 114.75(14) yes
C6 . C7 . H71 . 113.1 no
C8 . C7 . H71 . 112.5 no
O2 . C7 . H71 . 110.6 no
C7 . C8 . C9 . 102.53(15) yes
C7 . C8 . H82 . 110.1 no
C9 . C8 . H82 . 109.4 no
C7 . C8 . H81 . 113.4 no
C9 . C8 . H81 . 112.3 no
H82 . C8 . H81 . 109.0 no
C8 . C9 . C10 . 116.29(16) yes
C8 . C9 . O1 . 106.27(15) yes
C10 . C9 . O1 . 108.80(15) yes
C8 . C9 . H91 . 109.6 no
C10 . C9 . H91 . 109.0 no
O1 . C9 . H91 . 106.4 no
C9 . C10 . C11 . 118.71(15) yes
C9 . C10 . O16 . 107.37(14) yes
C11 . C10 . O16 . 110.40(15) yes
C9 . C10 . H101 . 106.9 no
C11 . C10 . H101 . 105.9 no
O16 . C10 . H101 . 106.9 no
C10 . C11 . C12 . 117.88(14) yes
C10 . C11 . H111 . 107.0 no
C12 . C11 . H111 . 109.2 no
C10 . C11 . H112 . 107.0 no
C12 . C11 . H112 . 105.1 no
H111 . C11 . H112 . 110.6 no
C11 . C12 . C13 . 113.28(14) yes
C11 . C12 . O17 . 109.77(14) yes
C13 . C12 . O17 . 114.17(15) yes
C11 . C12 . H121 . 107.2 no
C13 . C12 . H121 . 104.3 no
O17 . C12 . H121 . 107.5 no
C12 . C13 . C14 . 113.93(16) yes
C12 . C13 . O2 . 114.53(15) yes
C14 . C13 . O2 . 113.67(17) yes
C12 . C13 . H131 . 103.8 no
C14 . C13 . H131 . 105.2 no
O2 . C13 . H131 . 104.1 no
C13 . C14 . C15 . 111.98(17) yes
C13 . C14 . H142 . 110.3 no
C15 . C14 . H142 . 108.2 no
C13 . C14 . H141 . 109.3 no
C15 . C14 . H141 . 108.9 no
H142 . C14 . H141 . 108.1 no
C14 . C15 . H151 . 110.7 no
C14 . C15 . H152 . 108.3 no
H151 . C15 . H152 . 109.5 no
C14 . C15 . H153 . 110.8 no
H151 . C15 . H153 . 107.9 no
H152 . C15 . H153 . 109.6 no
C9 . O1 . C6 . 108.58(16) yes
C7 . O2 . C13 . 121.17(13) yes
C12 . O17 . H171 . 120(3) no
C10 . O16 . H161 . 111(2) no
C104 . C103 . H1031 . 120.2 no
C104 . C103 . H1032 . 119.3 no
H1031 . C103 . H1032 . 120.5 no
C4 . C3 . H32 . 120.6 no
C4 . C3 . H31 . 121.9 no
H32 . C3 . H31 . 117.5 no
C3 . C4 . C5 . 120.5(6) yes
C3 . C4 . H41 . 119.8 no
C5 . C4 . H41 . 119.7 no
C103 . C104 . C5 . 121.5(5) yes
C103 . C104 . H1041 . 118.7 no
C5 . C104 . H1041 . 119.8 no
C6 . C5 . C4 . 106.9(2) yes
C6 . C5 . H52 . 108.0 no
C4 . C5 . H52 . 108.9 no
C6 . C5 . H54 . 111.0 no
C4 . C5 . H54 . 113.1 no
H52 . C5 . H54 . 108.8 no
C6 . C5 . C104 . 113.4(2) yes
C6 . C5 . H53 . 109.0 no
C104 . C5 . H53 . 110.0 no
C6 . C5 . H51 . 107.6 no
C104 . C5 . H51 . 107.6 no
H53 . C5 . H51 . 109.1 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C6 . C7 . 1.527(3) yes
C6 . O1 . 1.433(3) yes
C6 . C5 . 1.517(3) yes
C6 . H61 . 0.998 no
C7 . C8 . 1.526(2) yes
C7 . O2 . 1.427(2) yes
C7 . H71 . 0.967 no
C8 . C9 . 1.534(3) yes
C8 . H82 . 0.956 no
C8 . H81 . 0.965 no
C9 . C10 . 1.533(3) yes
C9 . O1 . 1.437(2) yes
C9 . H91 . 0.992 no
C10 . C11 . 1.532(2) yes
C10 . O16 . 1.445(2) yes
C10 . H101 . 0.964 no
C11 . C12 . 1.537(3) yes
C11 . H111 . 0.965 no
C11 . H112 . 0.962 no
C12 . C13 . 1.552(2) yes
C12 . O17 . 1.441(2) yes
C12 . H121 . 0.957 no
C13 . C14 . 1.534(3) yes
C13 . O2 . 1.426(2) yes
C13 . H131 . 0.967 no
C14 . C15 . 1.527(3) yes
C14 . H142 . 0.963 no
C14 . H141 . 0.965 no
C15 . H151 . 0.950 no
C15 . H152 . 0.946 no
C15 . H153 . 0.953 no
O17 . H171 . 0.805(18) no
O16 . H161 . 0.812(18) no
C103 . C104 . 1.315(9) yes
C103 . H1031 . 0.930 no
C103 . H1032 . 0.933 no
C3 . C4 . 1.307(11) yes
C3 . H32 . 0.932 no
C3 . H31 . 0.933 no
C4 . C5 . 1.512(5) yes
C4 . H41 . 0.935 no
C104 . C5 . 1.566(5) yes
C104 . H1041 . 0.941 no
C5 . H52 . 0.973 no
C5 . H54 . 0.982 no
C5 . H53 . 0.974 no
C5 . H51 . 0.974 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C8 . H81 . O17 . 144 0.96 2.18 3.013(5) yes
O17 . H171 . C10 2_555 155(3) 0.805 2.581 3.326(5) yes
O17 . H171 . O16 2_555 170(4) 0.805 1.851 2.648(5) yes
O16 . H161 . O17 . 140(3) 0.812 1.946 2.618(5) yes
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
-6 -1 11 x .
