#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/09/7230945.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_7230945
loop_
_publ_author_name
'Sha, Hong-Kai'
'Liu, Feng'
'Lu, Juan'
'Liu, Zhang-Qin'
'Hao, Wen-Juan'
'Tang, Jia-Le'
'Tu, Shu-Jiang'
'Jiang, Bo'
_publ_section_title
;
 Metal-free benzannulation of yne-allenone esters for atom economical
 synthesis of functionalized 1-naphthols
;
_journal_issue                   15
_journal_name_full               'Green Chemistry'
_journal_page_first              3476
_journal_paper_doi               10.1039/C8GC01034J
_journal_volume                  20
_journal_year                    2018
_chemical_formula_sum            'C21 H18 O4'
_chemical_formula_weight         334.35
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2018-04-01 deposited with the CCDC.
2018-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.898(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.0463(15)
_cell_length_b                   11.4307(11)
_cell_length_c                   18.4621(16)
_cell_measurement_reflns_used    1209
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.172
_cell_measurement_theta_min      2.281
_cell_volume                     3423.3(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_sigmaI/netI    0.1735
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8441
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_correction_T_min  0.9694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.1499
_refine_ls_R_factor_gt           0.0645
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1741
_refine_ls_wR_factor_ref         0.2243
_reflns_number_gt                1382
_reflns_number_total             3023
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8gc01034j2.cif
_cod_data_source_block           160928e
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 7230945--7230946.cif.
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7230945
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.4283(2) 0.5612(4) 0.6407(2) 0.1148(14) Uani 1 1 d .
O2 O 0.30692(18) 0.6459(3) 0.60590(18) 0.0918(11) Uani 1 1 d .
O3 O 0.34608(15) 0.9046(3) 0.37976(14) 0.0674(9) Uani 1 1 d .
H3 H 0.3011 0.9040 0.3873 0.101 Uiso 1 1 calc R
O4 O 0.61864(16) 0.8155(2) 0.70005(15) 0.0645(8) Uani 1 1 d .
C1 C 0.3795(3) 0.6548(4) 0.6287(2) 0.0642(12) Uani 1 1 d .
C2 C 0.4266(2) 0.7644(4) 0.6422(2) 0.0662(12) Uani 1 1 d .
H2A H 0.4757 0.7545 0.6854 0.079 Uiso 1 1 calc R
H2B H 0.3935 0.8257 0.6546 0.079 Uiso 1 1 calc R
C3 C 0.4514(2) 0.8016(3) 0.57372(19) 0.0484(10) Uani 1 1 d .
C4 C 0.3888(2) 0.8380(3) 0.5086(2) 0.0500(10) Uani 1 1 d .
H4 H 0.3346 0.8406 0.5098 0.060 Uiso 1 1 calc R
C5 C 0.4054(2) 0.8696(3) 0.4439(2) 0.0483(10) Uani 1 1 d .
C6 C 0.4870(2) 0.8683(3) 0.4408(2) 0.0466(9) Uani 1 1 d .
C7 C 0.5069(2) 0.9040(4) 0.3752(2) 0.0570(11) Uani 1 1 d .
H7 H 0.4651 0.9280 0.3323 0.068 Uiso 1 1 calc R
C8 C 0.5862(3) 0.9036(4) 0.3742(2) 0.0677(12) Uani 1 1 d .
H8 H 0.5981 0.9257 0.3302 0.081 Uiso 1 1 calc R
C9 C 0.6498(3) 0.8703(4) 0.4385(3) 0.0631(12) Uani 1 1 d .
H9 H 0.7040 0.8715 0.4375 0.076 Uiso 1 1 calc R
C10 C 0.6332(2) 0.8357(3) 0.5032(2) 0.0520(10) Uani 1 1 d .
H10 H 0.6764 0.8139 0.5457 0.062 Uiso 1 1 calc R
C11 C 0.5515(2) 0.8325(3) 0.5065(2) 0.0428(9) Uani 1 1 d .
C12 C 0.5314(2) 0.7974(3) 0.57298(19) 0.0418(9) Uani 1 1 d .
C13 C 0.5991(2) 0.7572(3) 0.6418(2) 0.0451(9) Uani 1 1 d .
C14 C 0.6394(2) 0.6424(3) 0.6390(2) 0.0463(9) Uani 1 1 d .
C15 C 0.7110(2) 0.6132(4) 0.6962(2) 0.0557(11) Uani 1 1 d .
H15 H 0.7352 0.6670 0.7343 0.067 Uiso 1 1 calc R
C16 C 0.7461(2) 0.5047(4) 0.6967(3) 0.0661(12) Uani 1 1 d .
H16 H 0.7944 0.4857 0.7349 0.079 Uiso 1 1 calc R
C17 C 0.7104(3) 0.4250(4) 0.6414(3) 0.0713(13) Uani 1 1 d .
H17 H 0.7340 0.3514 0.6426 0.086 Uiso 1 1 calc R
C18 C 0.6401(3) 0.4524(4) 0.5844(3) 0.0753(13) Uani 1 1 d .
H18 H 0.6164 0.3977 0.5467 0.090 Uiso 1 1 calc R
C19 C 0.6038(2) 0.5616(4) 0.5825(2) 0.0593(11) Uani 1 1 d .
H19 H 0.5559 0.5803 0.5437 0.071 Uiso 1 1 calc R
C20 C 0.3944(5) 0.4419(6) 0.6244(4) 0.135(2) Uani 1 1 d .
H20A H 0.3466 0.4430 0.5793 0.162 Uiso 1 1 calc R
H20B H 0.4354 0.3908 0.6145 0.162 Uiso 1 1 calc R
C21 C 0.3714(5) 0.3979(7) 0.6877(5) 0.171(3) Uani 1 1 d .
H21A H 0.4199 0.3870 0.7305 0.257 Uiso 1 1 calc R
H21B H 0.3435 0.3244 0.6742 0.257 Uiso 1 1 calc R
H21C H 0.3353 0.4528 0.7008 0.257 Uiso 1 1 calc R
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'
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
C1 O1 C20 121.6(5)
C5 O3 H3 109.5
O2 C1 O1 121.5(5)
O2 C1 C2 126.3(4)
O1 C1 C2 112.1(4)
C1 C2 C3 112.2(3)
C1 C2 H2A 109.2
C3 C2 H2A 109.2
C1 C2 H2B 109.2
C3 C2 H2B 109.2
H2A C2 H2B 107.9
C12 C3 C4 120.0(3)
C12 C3 C2 122.3(3)
C4 C3 C2 117.7(3)
C5 C4 C3 121.5(3)
C5 C4 H4 119.2
C3 C4 H4 119.2
C4 C5 O3 122.9(3)
C4 C5 C6 120.5(3)
O3 C5 C6 116.5(3)
C5 C6 C7 122.1(3)
C5 C6 C11 118.8(3)
C7 C6 C11 119.1(3)
C8 C7 C6 120.9(4)
C8 C7 H7 119.6
C6 C7 H7 119.6
C7 C8 C9 120.4(4)
C7 C8 H8 119.8
C9 C8 H8 119.8
C10 C9 C8 120.5(4)
C10 C9 H9 119.7
C8 C9 H9 119.7
C9 C10 C11 121.1(4)
C9 C10 H10 119.4
C11 C10 H10 119.4
C10 C11 C6 118.0(3)
C10 C11 C12 123.0(3)
C6 C11 C12 119.1(3)
C3 C12 C11 120.1(3)
C3 C12 C13 120.7(3)
C11 C12 C13 119.2(3)
O4 C13 C14 120.5(3)
O4 C13 C12 120.6(3)
C14 C13 C12 118.8(3)
C19 C14 C15 119.5(4)
C19 C14 C13 120.9(3)
C15 C14 C13 119.5(4)
C16 C15 C14 120.1(4)
C16 C15 H15 120.0
C14 C15 H15 120.0
C17 C16 C15 120.2(4)
C17 C16 H16 119.9
C15 C16 H16 119.9
C16 C17 C18 120.5(4)
C16 C17 H17 119.8
C18 C17 H17 119.8
C17 C18 C19 120.3(4)
C17 C18 H18 119.9
C19 C18 H18 119.9
C14 C19 C18 119.4(4)
C14 C19 H19 120.3
C18 C19 H19 120.3
C21 C20 O1 110.2(6)
C21 C20 H20A 109.6
O1 C20 H20A 109.6
C21 C20 H20B 109.6
O1 C20 H20B 109.6
H20A C20 H20B 108.1
C20 C21 H21A 109.5
C20 C21 H21B 109.5
H21A C21 H21B 109.5
C20 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.332(5)
O1 C20 1.475(7)
O2 C1 1.182(4)
O3 C5 1.360(4)
O3 H3 0.8200
O4 C13 1.221(4)
C1 C2 1.468(6)
C2 C3 1.511(5)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C12 1.369(5)
C3 C4 1.403(5)
C4 C5 1.359(5)
C4 H4 0.9300
C5 C6 1.410(5)
C6 C7 1.413(5)
C6 C11 1.424(5)
C7 C8 1.357(5)
C7 H7 0.9300
C8 C9 1.393(6)
C8 H8 0.9300
C9 C10 1.367(5)
C9 H9 0.9300
C10 C11 1.412(4)
C10 H10 0.9300
C11 C12 1.430(4)
C12 C13 1.502(5)
C13 C14 1.490(5)
C14 C19 1.385(5)
C14 C15 1.387(5)
C15 C16 1.376(6)
C15 H15 0.9300
C16 C17 1.365(6)
C16 H16 0.9300
C17 C18 1.366(6)
C17 H17 0.9300
C18 C19 1.389(6)
C18 H18 0.9300
C19 H19 0.9300
C20 C21 1.433(8)
C20 H20A 0.9700
C20 H20B 0.9700
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C20 O1 C1 O2 1.6(7)
C20 O1 C1 C2 -174.8(4)
O2 C1 C2 C3 -92.7(5)
O1 C1 C2 C3 83.4(4)
C1 C2 C3 C12 -109.5(4)
C1 C2 C3 C4 68.6(5)
C12 C3 C4 C5 0.0(6)
C2 C3 C4 C5 -178.1(4)
C3 C4 C5 O3 179.6(3)
C3 C4 C5 C6 -1.0(6)
C4 C5 C6 C7 -178.1(4)
O3 C5 C6 C7 1.4(5)
C4 C5 C6 C11 0.5(5)
O3 C5 C6 C11 179.9(3)
C5 C6 C7 C8 178.9(4)
C11 C6 C7 C8 0.4(6)
C6 C7 C8 C9 -1.4(6)
C7 C8 C9 C10 1.1(6)
C8 C9 C10 C11 0.2(6)
C9 C10 C11 C6 -1.1(5)
C9 C10 C11 C12 -179.7(3)
C5 C6 C11 C10 -177.8(3)
C7 C6 C11 C10 0.8(5)
C5 C6 C11 C12 0.9(5)
C7 C6 C11 C12 179.4(3)
C4 C3 C12 C11 1.3(5)
C2 C3 C12 C11 179.3(3)
C4 C3 C12 C13 -179.2(3)
C2 C3 C12 C13 -1.2(5)
C10 C11 C12 C3 176.8(3)
C6 C11 C12 C3 -1.8(5)
C10 C11 C12 C13 -2.6(5)
C6 C11 C12 C13 178.8(3)
C3 C12 C13 O4 -67.4(5)
C11 C12 C13 O4 112.1(4)
C3 C12 C13 C14 109.9(4)
C11 C12 C13 C14 -70.6(4)
O4 C13 C14 C19 162.1(4)
C12 C13 C14 C19 -15.2(5)
O4 C13 C14 C15 -14.0(5)
C12 C13 C14 C15 168.8(3)
C19 C14 C15 C16 0.1(5)
C13 C14 C15 C16 176.2(3)
C14 C15 C16 C17 -0.7(6)
C15 C16 C17 C18 1.0(6)
C16 C17 C18 C19 -0.6(6)
C15 C14 C19 C18 0.3(6)
C13 C14 C19 C18 -175.7(3)
C17 C18 C19 C14 0.0(6)
C1 O1 C20 C21 -84.4(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139204817
