#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/01/1550136.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_1550136
loop_
_publ_author_name
'Condakes, Matthew'
'Rosen, Rachel'
'Harwood, Stephen'
'Maimone, Thomas'
_publ_section_title
;
 A Copper-Catalyzed Double Coupling Enables a 3-Step Synthesis of the
 Quassinoid Core Architecture
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C8SC03835J
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H24 O5'
_chemical_formula_sum            'C18 H24 O5'
_chemical_formula_weight         320.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           ' P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-07-09
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-07-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.7797(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0320(3)
_cell_length_b                   6.3518(2)
_cell_length_c                   16.1371(6)
_cell_measurement_reflns_used    16547
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.5250
_cell_measurement_theta_min      5.8380
_cell_volume                     821.49(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      99.97
_diffrn_measured_fraction_theta_full 0.9884
_diffrn_measured_fraction_theta_max 0.9884
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, Pilatus 200K'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20223
_diffrn_reflns_theta_full        68.2754
_diffrn_reflns_theta_max         68.28
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    0.768
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2951
_exptl_crystal_description       block
_exptl_crystal_F_000             345.1788
_refine_diff_density_max         0.1328
_refine_diff_density_min         -0.1242
_refine_diff_density_rms         0.0283
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.02(11)
_refine_ls_d_res_high            0.8298
_refine_ls_d_res_low             16.1020
_refine_ls_goodness_of_fit_ref   1.0956
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    4
_refine_ls_number_parameters     297
_refine_ls_number_reflns         2984
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0956
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0243
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0310P)²+0.1140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0616
_refine_ls_wR_factor_ref         0.0620
_reflns_Friedel_coverage         0.977
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              7
_reflns_limit_k_min              -7
_reflns_limit_l_max              19
_reflns_limit_l_min              -19
_reflns_number_gt                2920
_reflns_number_total             2984
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8sc03835j2.cif
_cod_data_source_block           MLC_LIT_dioxenecoupling
_cod_database_code               1550136
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_date_sample_completion    2015-05-27
_olex2_date_sample_data_collection 2015-05-26
_olex2_date_sample_submission    2015-05-26
_olex2_submission_original_sample_id MLC-II-225
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -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_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
O1 O -0.23489(11) -0.02179(14) 0.32337(6) 0.0267(2) Uani 1.000000 .
O2 O -0.74511(11) -0.08609(14) 0.10441(6) 0.0281(2) Uani 1.000000 .
H2 H -0.7569(11) 0.0452(3) 0.1064(10) 0.0422(3) Uiso 1.000000 GR
O3 O -0.24809(11) 0.48040(14) 0.15815(6) 0.0251(2) Uani 1.000000 .
O4 O -0.09417(11) 0.33373(15) 0.41352(6) 0.0309(2) Uani 1.000000 .
O5 O 0.04566(12) 0.29656(14) 0.09742(6) 0.0301(2) Uani 1.000000 .
C6 C -0.37942(14) 0.14293(18) 0.16412(7) 0.0195(2) Uani 1.000000 .
C7 C -0.62843(16) 0.1141(2) 0.36295(8) 0.0274(3) Uani 1.000000 .
C8 C -0.43741(15) 0.20356(19) 0.24928(8) 0.0203(2) Uani 1.000000 .
C9 C -0.29425(15) 0.1816(2) 0.31335(7) 0.0214(3) Uani 1.000000 .
C10 C -0.23314(16) 0.26697(18) 0.14186(7) 0.0201(3) Uani 1.000000 .
C11 C -0.09390(15) 0.1845(2) 0.11576(8) 0.0240(3) Uani 1.000000 .
H11 H -0.09036(15) 0.0360(2) 0.10922(8) 0.0288(3) Uiso 1.000000 R
C12 C -0.40300(16) -0.0641(2) 0.03017(8) 0.0246(3) Uani 1.000000 .
C13 C -0.44876(14) -0.0107(2) 0.11652(7) 0.0206(2) Uani 1.000000 .
C14 C -0.22587(15) 0.3459(2) 0.35393(8) 0.0249(3) Uani 1.000000 .
C15 C -0.61653(18) -0.0429(2) 0.41712(9) 0.0328(3) Uani 1.000000 .
C16 C -0.58785(15) -0.1445(2) 0.14702(8) 0.0229(3) Uani 1.000000 .
C17 C -0.07123(17) -0.0239(2) 0.36504(9) 0.0324(3) Uani 1.000000 .
C18 C -0.06505(19) 0.1210(3) 0.43925(9) 0.0343(3) Uani 1.000000 .
C19 C -0.59925(15) 0.0875(2) 0.27125(8) 0.0228(3) Uani 1.000000 .
C20 C -0.59669(16) -0.1388(2) 0.24088(8) 0.0236(3) Uani 1.000000 .
C21 C -0.08756(19) 0.5781(2) 0.16806(9) 0.0313(3) Uani 1.000000 .
C22 C 0.0137(2) 0.5199(2) 0.09606(10) 0.0345(3) Uani 1.000000 .
C23 C -0.67151(19) 0.3323(2) 0.38847(10) 0.0338(3) Uani 1.000000 .
H17a H -0.050(2) -0.171(3) 0.3813(11) 0.038(4) Uiso 1.000000 .
H8 H -0.4623(18) 0.349(3) 0.2476(9) 0.023(3) Uiso 1.000000 .
H12a H -0.503(2) -0.086(3) -0.0056(10) 0.026(3) Uiso 1.000000 .
H21a H -0.1037(19) 0.729(3) 0.1691(10) 0.027(4) Uiso 1.000000 .
H14 H -0.2630(18) 0.497(3) 0.3433(9) 0.022(3) Uiso 1.000000 .
H19 H -0.6900(17) 0.162(2) 0.2405(8) 0.016(3) Uiso 1.000000 .
H12b H -0.338(2) -0.197(3) 0.0322(11) 0.037(4) Uiso 1.000000 .
H15a H -0.589(2) -0.194(3) 0.4017(12) 0.044(5) Uiso 1.000000 .
H22a H 0.124(2) 0.590(3) 0.1007(10) 0.033(4) Uiso 1.000000 .
H15b H -0.633(2) -0.014(3) 0.4738(11) 0.033(4) Uiso 1.000000 .
H23a H -0.775(2) 0.374(3) 0.3583(10) 0.032(4) Uiso 1.000000 .
H18a H -0.152(2) 0.083(3) 0.4754(11) 0.036(4) Uiso 1.000000 .
H16 H -0.5673(16) -0.291(2) 0.1324(8) 0.015(3) Uiso 1.000000 .
H20a H -0.7024(19) -0.216(2) 0.2552(9) 0.022(4) Uiso 1.000000 .
H23b H -0.592(2) 0.438(3) 0.3738(11) 0.043(5) Uiso 1.000000 .
H23c H -0.681(2) 0.348(3) 0.4474(12) 0.045(5) Uiso 1.000000 .
H18b H 0.043(2) 0.116(3) 0.4703(10) 0.033(4) Uiso 1.000000 .
H20b H -0.5042(19) -0.214(2) 0.2648(9) 0.020(4) Uiso 1.000000 .
H17b H 0.011(2) 0.025(2) 0.3216(10) 0.030(4) Uiso 1.000000 .
H22b H -0.044(2) 0.555(3) 0.0432(11) 0.039(5) Uiso 1.000000 .
H21b H -0.026(2) 0.528(2) 0.2220(10) 0.030(4) Uiso 1.000000 .
H12c H -0.339(2) 0.054(3) 0.0077(10) 0.029(4) Uiso 1.000000 .
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_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03376 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C17 O1 C9 111.16(10)
C21 O3 C10 110.88(11)
C18 O4 C14 110.97(10)
C22 O5 C11 111.44(10)
C10 C6 C8 112.22(10)
C13 C6 C8 123.97(10)
C13 C6 C10 123.76(11)
C19 C7 C15 123.26(13)
C23 C7 C15 121.64(13)
C23 C7 C19 115.10(12)
C9 C8 C6 109.31(9)
C19 C8 C6 113.21(10)
C19 C8 C9 114.37(10)
C8 C9 O1 114.18(10)
C14 C9 O1 123.16(11)
C14 C9 C8 122.58(12)
C6 C10 O3 113.23(10)
C11 C10 O3 122.03(11)
C11 C10 C6 124.48(11)
C10 C11 O5 125.39(11)
C12 C13 C6 125.29(11)
C16 C13 C6 120.72(11)
C16 C13 C12 113.97(10)
C9 C14 O4 124.72(13)
C13 C16 O2 110.02(10)
C20 C16 O2 111.75(10)
C20 C16 C13 113.26(10)
C18 C17 O1 110.32(12)
C17 C18 O4 110.49(11)
C8 C19 C7 110.70(10)
C20 C19 C7 115.12(11)
C20 C19 C8 110.21(10)
C19 C20 C16 110.25(10)
C22 C21 O3 109.61(12)
C21 C22 O5 109.51(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.3830(15)
O1 C17 1.4366(16)
O2 C16 1.4460(15)
O3 C10 1.3876(15)
O3 C21 1.4304(17)
O4 C14 1.3840(15)
O4 C18 1.4286(19)
O5 C11 1.3763(15)
O5 C22 1.4415(18)
C6 C8 1.5291(16)
C6 C10 1.4785(17)
C6 C13 1.3403(17)
C7 C15 1.325(2)
C7 C19 1.5227(17)
C7 C23 1.493(2)
C8 C9 1.5013(16)
C8 C19 1.5555(16)
C9 C14 1.3312(19)
C10 C11 1.3283(18)
C12 C13 1.5031(16)
C13 C16 1.5114(16)
C16 C20 1.5214(17)
C17 C18 1.508(2)
C19 C20 1.5193(18)
C21 C22 1.508(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139052568
