#------------------------------------------------------------------------------
#$Date: 2022-05-05 23:40:35 +0300 (Thu, 05 May 2022) $
#$Revision: 275000 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/13/7061312.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_7061312
loop_
_publ_author_name
'Gharpure, Santosh J.'
'Jegadeesan, S.'
'Vishwakarma, Dharmendra S.'
_publ_section_title
;
 Total synthesis of myristinins A--F and
 3′-hydroxy-5,7-dimethoxy-4-O-2′-cycloflavan by iterative
 generation of o-quinone methides
;
_journal_issue                   12
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              5460
_journal_page_last               5463
_journal_paper_doi               10.1039/D2NJ00244B
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C17 H16 O4'
_chemical_formula_sum            'C17 H16 O4'
_chemical_formula_weight         284.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-01-13
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2021-07-16 deposited with the CCDC.	2022-02-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.301(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.3610(14)
_cell_length_b                   10.1907(8)
_cell_length_c                   15.3314(10)
_cell_measurement_reflns_used    6928
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.38
_cell_volume                     2668.7(3)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            34580
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.329
_diffrn_reflns_theta_min         2.327
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0812 before and 0.0614 after correction.
The Ratio of minimum to maximum transmission is 0.9410.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3315
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0399
_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)+(0.0432P)²+1.6487P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1049
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2560
_reflns_number_total             3315
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj00244b2.cif
_cod_data_source_block           sjg_dsv_11_45_0m
_cod_depositor_comments
'Adding full bibliography for 7061308--7061314.cif.'
_cod_database_code               7061312
_shelx_shelxl_version_number     2018/3
_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   0.998
_shelx_estimated_absorpt_t_min   0.980
_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:
 C4(H4), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C6(H6), C7(H7), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C15(H15A,H15B,H15C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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 0.43432(6) -0.00661(9) 0.34202(7) 0.0308(2) Uani 1 1 d . . . . .
O2 O 0.49175(6) 0.52682(10) 0.37412(8) 0.0404(3) Uani 1 1 d . . . . .
O3 O 0.15459(6) 0.23899(9) 0.37990(6) 0.0271(2) Uani 1 1 d . . . . .
O4 O 0.25202(5) 0.18036(9) 0.27460(6) 0.0237(2) Uani 1 1 d . . . . .
C1 C 0.24286(9) -0.06129(14) 0.48958(9) 0.0311(3) Uani 1 1 d . . . . .
H1 H 0.239972 -0.115868 0.539128 0.037 Uiso 1 1 calc R . . . .
C2 C 0.29384(8) -0.09273(13) 0.43384(9) 0.0291(3) Uani 1 1 d . . . . .
H2 H 0.325950 -0.168499 0.445172 0.035 Uiso 1 1 calc R . . . .
C3 C 0.29865(8) -0.01364(12) 0.36047(9) 0.0249(3) Uani 1 1 d . . . . .
C4 C 0.35587(8) -0.04604(13) 0.30018(9) 0.0289(3) Uani 1 1 d . . . . .
H4 H 0.355261 -0.142896 0.289616 0.035 Uiso 1 1 calc R . . . .
C5 C 0.44484(8) 0.12792(13) 0.34667(8) 0.0246(3) Uani 1 1 d . . . . .
C6 C 0.51110(8) 0.17459(13) 0.40330(9) 0.0267(3) Uani 1 1 d . . . . .
H6 H 0.546507 0.114664 0.436873 0.032 Uiso 1 1 calc R . . . .
C7 C 0.52524(8) 0.30770(14) 0.41058(9) 0.0277(3) Uani 1 1 d . . . . .
H7 H 0.570761 0.339165 0.448601 0.033 Uiso 1 1 calc R . . . .
C8 C 0.47284(8) 0.39648(13) 0.36221(9) 0.0270(3) Uani 1 1 d . . . . .
C9 C 0.43565(10) 0.61820(16) 0.33034(13) 0.0520(5) Uani 1 1 d . . . . .
H9A H 0.429680 0.606314 0.266047 0.078 Uiso 1 1 calc GR . . . .
H9B H 0.453528 0.707770 0.345989 0.078 Uiso 1 1 calc GR . . . .
H9C H 0.385186 0.603340 0.348877 0.078 Uiso 1 1 calc GR . . . .
C10 C 0.39287(8) 0.21526(13) 0.29744(8) 0.0232(3) Uani 1 1 d . . . . .
C11 C 0.32166(8) 0.16630(13) 0.23459(8) 0.0245(3) Uani 1 1 d . . . . .
H11 H 0.314810 0.219192 0.178790 0.029 Uiso 1 1 calc R . . . .
C12 C 0.33284(9) 0.02356(14) 0.21244(9) 0.0304(3) Uani 1 1 d . . . . .
H12A H 0.283673 -0.013564 0.178813 0.037 Uiso 1 1 calc R . . . .
H12B H 0.374457 0.014481 0.176338 0.037 Uiso 1 1 calc R . . . .
C13 C 0.25075(8) 0.09667(12) 0.34455(8) 0.0225(3) Uani 1 1 d . . . . .
C14 C 0.19830(8) 0.12879(13) 0.40147(8) 0.0238(3) Uani 1 1 d . . . . .
C15 C 0.10836(9) 0.28239(15) 0.44271(10) 0.0314(3) Uani 1 1 d . . . . .
H15A H 0.074074 0.210935 0.455023 0.047 Uiso 1 1 calc GR . . . .
H15B H 0.076448 0.357665 0.418402 0.047 Uiso 1 1 calc GR . . . .
H15C H 0.142865 0.308336 0.497768 0.047 Uiso 1 1 calc GR . . . .
C16 C 0.19534(8) 0.04952(14) 0.47447(9) 0.0290(3) Uani 1 1 d . . . . .
H16 H 0.160929 0.070829 0.514086 0.035 Uiso 1 1 calc R . . . .
C17 C 0.40720(8) 0.35033(13) 0.30597(8) 0.0250(3) Uani 1 1 d . . . . .
H17 H 0.371624 0.410539 0.272941 0.030 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C4 113.65(10) . . ?
C8 O2 C9 116.26(11) . . ?
C14 O3 C15 116.54(10) . . ?
C13 O4 C11 113.46(10) . . ?
C2 C1 H1 119.5 . . ?
C2 C1 C16 120.92(13) . . ?
C16 C1 H1 119.5 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.26(13) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 120.47(12) . . ?
C13 C3 C2 119.09(13) . . ?
C13 C3 C4 120.43(12) . . ?
O1 C4 C3 109.65(11) . . ?
O1 C4 H4 109.0 . . ?
O1 C4 C12 109.94(12) . . ?
C3 C4 H4 109.0 . . ?
C3 C4 C12 110.15(11) . . ?
C12 C4 H4 109.0 . . ?
O1 C5 C6 117.16(12) . . ?
O1 C5 C10 122.66(12) . . ?
C10 C5 C6 120.17(12) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.03(12) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.26(13) . . ?
C8 C7 H7 119.9 . . ?
O2 C8 C7 115.99(12) . . ?
O2 C8 C17 124.27(12) . . ?
C17 C8 C7 119.74(12) . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 C11 120.85(12) . . ?
C5 C10 C17 119.43(12) . . ?
C17 C10 C11 119.71(12) . . ?
O4 C11 C10 110.19(10) . . ?
O4 C11 H11 109.1 . . ?
O4 C11 C12 109.76(11) . . ?
C10 C11 H11 109.1 . . ?
C10 C11 C12 109.72(11) . . ?
C12 C11 H11 109.1 . . ?
C4 C12 C11 106.00(11) . . ?
C4 C12 H12A 110.5 . . ?
C4 C12 H12B 110.5 . . ?
C11 C12 H12A 110.5 . . ?
C11 C12 H12B 110.5 . . ?
H12A C12 H12B 108.7 . . ?
O4 C13 C3 123.04(12) . . ?
O4 C13 C14 116.25(11) . . ?
C3 C13 C14 120.71(12) . . ?
O3 C14 C13 115.78(11) . . ?
O3 C14 C16 125.16(12) . . ?
C16 C14 C13 119.06(13) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 C16 H16 120.0 . . ?
C14 C16 C1 119.95(13) . . ?
C14 C16 H16 120.0 . . ?
C8 C17 C10 120.35(12) . . ?
C8 C17 H17 119.8 . . ?
C10 C17 H17 119.8 . . ?
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 C4 1.4545(17) . ?
O1 C5 1.3832(16) . ?
O2 C8 1.3725(16) . ?
O2 C9 1.4256(18) . ?
O3 C14 1.3625(16) . ?
O3 C15 1.4295(16) . ?
O4 C11 1.4572(16) . ?
O4 C13 1.3735(15) . ?
C1 H1 0.9500 . ?
C1 C2 1.374(2) . ?
C1 C16 1.393(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.3983(19) . ?
C3 C4 1.5095(19) . ?
C3 C13 1.3938(18) . ?
C4 H4 1.0000 . ?
C4 C12 1.5099(19) . ?
C5 C6 1.3950(19) . ?
C5 C10 1.3900(18) . ?
C6 H6 0.9500 . ?
C6 C7 1.3795(19) . ?
C7 H7 0.9500 . ?
C7 C8 1.3982(19) . ?
C8 C17 1.3827(19) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.5099(18) . ?
C10 C17 1.4007(19) . ?
C11 H11 1.0000 . ?
C11 C12 1.5141(18) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.4080(18) . ?
C14 C16 1.3887(18) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C4 C12 C11 -69.88(14) . . . . ?
O1 C5 C6 C7 179.63(12) . . . . ?
O1 C5 C10 C11 -0.75(19) . . . . ?
O1 C5 C10 C17 179.68(12) . . . . ?
O2 C8 C17 C10 179.48(13) . . . . ?
O3 C14 C16 C1 179.81(12) . . . . ?
O4 C11 C12 C4 -69.65(14) . . . . ?
O4 C13 C14 O3 0.41(17) . . . . ?
O4 C13 C14 C16 -178.72(11) . . . . ?
C1 C2 C3 C4 178.62(12) . . . . ?
C1 C2 C3 C13 -0.40(19) . . . . ?
C2 C1 C16 C14 1.0(2) . . . . ?
C2 C3 C4 O1 -77.18(15) . . . . ?
C2 C3 C4 C12 161.71(12) . . . . ?
C2 C3 C13 O4 179.44(11) . . . . ?
C2 C3 C13 C14 0.21(19) . . . . ?
C3 C4 C12 C11 51.06(14) . . . . ?
C3 C13 C14 O3 179.70(11) . . . . ?
C3 C13 C14 C16 0.56(19) . . . . ?
C4 O1 C5 C6 165.35(12) . . . . ?
C4 O1 C5 C10 -15.02(17) . . . . ?
C4 C3 C13 O4 0.42(19) . . . . ?
C4 C3 C13 C14 -178.81(12) . . . . ?
C5 O1 C4 C3 -70.51(14) . . . . ?
C5 O1 C4 C12 50.73(14) . . . . ?
C5 C6 C7 C8 0.8(2) . . . . ?
C5 C10 C11 O4 101.76(13) . . . . ?
C5 C10 C11 C12 -19.20(17) . . . . ?
C5 C10 C17 C8 0.62(19) . . . . ?
C6 C5 C10 C11 178.88(12) . . . . ?
C6 C5 C10 C17 -0.70(19) . . . . ?
C6 C7 C8 O2 179.74(12) . . . . ?
C6 C7 C8 C17 -0.9(2) . . . . ?
C7 C8 C17 C10 0.2(2) . . . . ?
C9 O2 C8 C7 -175.35(14) . . . . ?
C9 O2 C8 C17 5.3(2) . . . . ?
C10 C5 C6 C7 0.0(2) . . . . ?
C10 C11 C12 C4 51.56(14) . . . . ?
C11 O4 C13 C3 -16.71(16) . . . . ?
C11 O4 C13 C14 162.56(11) . . . . ?
C11 C10 C17 C8 -178.96(12) . . . . ?
C13 O4 C11 C10 -69.27(13) . . . . ?
C13 O4 C11 C12 51.67(13) . . . . ?
C13 C3 C4 O1 101.83(14) . . . . ?
C13 C3 C4 C12 -19.28(17) . . . . ?
C13 C14 C16 C1 -1.15(19) . . . . ?
C15 O3 C14 C13 -172.37(11) . . . . ?
C15 O3 C14 C16 6.70(18) . . . . ?
C16 C1 C2 C3 -0.2(2) . . . . ?
C17 C10 C11 O4 -78.67(14) . . . . ?
C17 C10 C11 C12 160.37(12) . . . . ?
