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#$Date: 2022-10-01 04:13:40 +0300 (Sat, 01 Oct 2022) $
#$Revision: 278295 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/56/7245601.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_7245601
loop_
_publ_author_name
'Phan, Gia Hung'
'Hu, Hao-Chun'
'Chang, Fang-Rong'
'Wen, Zhi-Hong'
'Chen, Jih-Jung'
'Chung, Hsu-Ming'
'Tsai, Yu-Chi'
'Sung, Ping-Jyun'
_publ_section_title
;
 Norsesquiterpenoids from the octocoral Paralemnalia thyrsoides (Ehrenberg
 1834)
;
_journal_issue                   43
_journal_name_full               'RSC Advances'
_journal_page_first              27970
_journal_page_last               27976
_journal_paper_doi               10.1039/D2RA05015C
_journal_volume                  12
_journal_year                    2022
_chemical_formula_sum            'C14 H21 Cl O3'
_chemical_formula_weight         272.76
_chemical_name_systematic        napalilactone
_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'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2019/1
_audit_update_record
;
2022-07-15 deposited with the CCDC.	2022-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2367(2)
_cell_length_b                   9.9002(3)
_cell_length_c                   17.2237(5)
_cell_measurement_reflns_used    19846
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      30.47
_cell_measurement_theta_min      2.37
_cell_volume                     1404.51(7)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.16'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'Bruker APEX4'
_computing_publication_material  'Bruker APEX4'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick 2015)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            39483
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.988
_diffrn_reflns_theta_min         2.365
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_correction_T_min  0.6668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015). 
"Comparison of silver and molybdenum microfocus X-ray sources for 
single-crystal structure determination" 
J. Appl. Cryst. 48, 3-10. 
doi:10.1107/S1600576714022985 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       lath
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.599
_exptl_crystal_size_mid          0.512
_exptl_crystal_size_min          0.081
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
; 
 Flack x determined using 1413 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.04(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         4100
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.159
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0406P)²+0.6043P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1248
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3494
_reflns_number_total             4100
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra05015c2.cif
_cod_data_source_block           ic21528
_cod_database_code               7245601
_shelx_shelxl_version_number     2019/1
_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_min   0.855
_shelx_estimated_absorpt_t_max   0.978
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.38179(10) 0.33622(9) 0.89907(5) 0.0494(2) Uani 1 1 d . . . . .
O1 O 0.6770(2) 0.43119(18) 0.80724(11) 0.0339(4) Uani 1 1 d . . . . .
O2 O 0.6649(3) 0.6458(2) 0.84524(16) 0.0522(6) Uani 1 1 d . . . . .
O3 O 0.9380(3) 0.0891(3) 0.63888(15) 0.0569(6) Uani 1 1 d . . . . .
C1 C 0.5186(4) 0.2349(3) 0.84004(17) 0.0359(6) Uani 1 1 d . . . . .
H1 H 0.468307 0.245186 0.788558 0.043 Uiso 1 1 d R U . . .
C2 C 0.5167(4) 0.0896(3) 0.8671(2) 0.0462(7) Uani 1 1 d . . . . .
H2A H 0.404292 0.054255 0.865681 0.055 Uiso 1 1 calc R U . . .
H2B H 0.556549 0.084139 0.921188 0.055 Uiso 1 1 calc R U . . .
C3 C 0.6252(5) 0.0052(3) 0.8140(2) 0.0466(7) Uani 1 1 d . . . . .
H3A H 0.577029 0.003107 0.761357 0.056 Uiso 1 1 calc R U . . .
H3B H 0.628325 -0.088757 0.833692 0.056 Uiso 1 1 calc R U . . .
C4 C 0.7994(4) 0.0592(3) 0.80843(17) 0.0388(6) Uani 1 1 d . . . . .
H4 H 0.845390 0.011878 0.763335 0.047 Uiso 1 1 d R U . . .
C5 C 0.8022(3) 0.2119(3) 0.78502(15) 0.0310(5) Uani 1 1 d . . . . .
C6 C 0.6896(3) 0.2959(2) 0.84037(15) 0.0308(5) Uani 1 1 d . . . . .
C7 C 0.6902(4) 0.5293(3) 0.86135(19) 0.0380(6) Uani 1 1 d . . . . .
C8 C 0.7389(4) 0.4704(3) 0.93801(18) 0.0415(6) Uani 1 1 d . . . . .
H8A H 0.655259 0.488812 0.977895 0.050 Uiso 1 1 calc R U . . .
H8B H 0.843544 0.508891 0.955633 0.050 Uiso 1 1 calc R U . . .
C9 C 0.7549(4) 0.3191(3) 0.92374(17) 0.0401(6) Uani 1 1 d . . . . .
H9A H 0.689981 0.267550 0.961995 0.048 Uiso 1 1 calc R U . . .
H9B H 0.869702 0.290436 0.927718 0.048 Uiso 1 1 calc R U . . .
C10 C 0.7348(4) 0.2283(3) 0.70151(16) 0.0367(6) Uani 1 1 d . . . . .
H10A H 0.618(5) 0.189(4) 0.697(2) 0.044 Uiso 1 1 d . U . . .
H10B H 0.722(4) 0.326(4) 0.690(2) 0.044 Uiso 1 1 d . U . . .
C11 C 0.8219(4) 0.1640(3) 0.63388(17) 0.0400(6) Uani 1 1 d . . . . .
C12 C 0.7503(6) 0.1982(4) 0.5560(2) 0.0622(10) Uani 1 1 d . . . . .
H12A H 0.807836 0.148074 0.515385 0.093 Uiso 1 1 calc R U . . .
H12B H 0.761426 0.295401 0.546516 0.093 Uiso 1 1 calc R U . . .
H12C H 0.635140 0.173526 0.555366 0.093 Uiso 1 1 calc R U . . .
C13 C 0.8973(5) 0.0216(4) 0.8807(2) 0.0542(9) Uani 1 1 d . . . . .
H13A H 0.844101 0.058696 0.926864 0.081 Uiso 1 1 calc R U . . .
H13B H 1.007163 0.058941 0.876343 0.081 Uiso 1 1 calc R U . . .
H13C H 0.903562 -0.076958 0.885095 0.081 Uiso 1 1 calc R U . . .
C14 C 0.9742(4) 0.2701(3) 0.7853(2) 0.0456(7) Uani 1 1 d . . . . .
H14A H 1.042501 0.218494 0.749419 0.068 Uiso 1 1 calc R U . . .
H14B H 1.019404 0.264339 0.837831 0.068 Uiso 1 1 calc R U . . .
H14C H 0.970744 0.364846 0.768881 0.068 Uiso 1 1 calc R U . . .
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'
Cl Cl 0.1484 0.1585 '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
C7 O1 C6 112.6(2) . . ?
C2 C1 C6 112.5(3) . . ?
C2 C1 Cl1 110.3(2) . . ?
C6 C1 Cl1 110.48(18) . . ?
C1 C2 C3 109.3(2) . . ?
C2 C3 C4 113.2(3) . . ?
C13 C4 C3 111.0(3) . . ?
C13 C4 C5 115.9(3) . . ?
C3 C4 C5 111.5(2) . . ?
C14 C5 C10 107.2(2) . . ?
C14 C5 C4 112.1(2) . . ?
C10 C5 C4 109.6(2) . . ?
C14 C5 C6 110.2(2) . . ?
C10 C5 C6 107.3(2) . . ?
C4 C5 C6 110.3(2) . . ?
O1 C6 C1 107.1(2) . . ?
O1 C6 C9 104.5(2) . . ?
C1 C6 C9 112.4(2) . . ?
O1 C6 C5 106.9(2) . . ?
C1 C6 C5 109.4(2) . . ?
C9 C6 C5 115.9(2) . . ?
O2 C7 O1 121.1(3) . . ?
O2 C7 C8 128.5(3) . . ?
O1 C7 C8 110.5(2) . . ?
C7 C8 C9 105.3(2) . . ?
C8 C9 C6 105.4(2) . . ?
C11 C10 C5 120.1(2) . . ?
O3 C11 C12 120.7(3) . . ?
O3 C11 C10 125.3(3) . . ?
C12 C11 C10 114.0(3) . . ?
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
Cl1 C1 1.819(3) . ?
O1 C7 1.351(3) . ?
O1 C6 1.460(3) . ?
O2 C7 1.205(4) . ?
O3 C11 1.213(4) . ?
C1 C2 1.511(4) . ?
C1 C6 1.533(4) . ?
C2 C3 1.528(5) . ?
C3 C4 1.534(5) . ?
C4 C13 1.529(4) . ?
C4 C5 1.565(4) . ?
C5 C14 1.529(4) . ?
C5 C10 1.550(4) . ?
C5 C6 1.568(4) . ?
C6 C9 1.550(4) . ?
C7 C8 1.498(5) . ?
C8 C9 1.523(4) . ?
C10 C11 1.509(4) . ?
C11 C12 1.504(5) . ?
