#------------------------------------------------------------------------------
#$Date: 2025-08-20 21:34:49 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301835 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/07/4130782.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_4130782
loop_
_publ_author_name
'Cernijenko, Artiom'
'Risgaard, Rune'
'Baran, Phil S.'
_publ_section_title
;
 11-Step Total Synthesis of (-)-Maoecrystal V.
;
_journal_issue                   30
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9425
_journal_page_last               9428
_journal_paper_doi               10.1021/jacs.6b06623
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C17 H22 O2'
_chemical_formula_sum            'C17 H22 O2'
_chemical_formula_weight         258.35
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.018(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9310(15)
_cell_length_b                   9.6410(13)
_cell_length_c                   13.213(2)
_cell_measurement_reflns_used    4005
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.27
_cell_measurement_theta_min      2.82
_cell_volume                     1391.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-I CCD'
_diffrn_measurement_method       'φ and ω 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  0.0549
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17032
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_correction_T_min  0.9844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2848
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0458P)²+0.8879P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1045
_refine_ls_wR_factor_ref         0.1187
_reflns_number_gt                2066
_reflns_number_total             2848
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja6b06623_si_003.cif
_cod_data_source_block           baran377
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_refine_ls_hydrogen_treatment' value 'CONSTR' was changed
to 'constr' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4130782
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.70190(12) 0.60508(15) 0.41845(10) 0.0249(3) Uani 1 1 d .
O2 O 0.59498(11) 0.90380(13) 0.37448(10) 0.0215(3) Uani 1 1 d .
C1 C 0.64503(17) 0.69384(19) 0.15986(14) 0.0185(4) Uani 1 1 d .
H1A H 0.5794 0.7225 0.1156 0.022 Uiso 1 1 calc R
C2 C 0.76747(17) 0.6743(2) 0.11469(15) 0.0221(4) Uani 1 1 d .
H2A H 0.8026 0.7662 0.0992 0.027 Uiso 1 1 calc R
H2B H 0.7570 0.6225 0.0503 0.027 Uiso 1 1 calc R
C3 C 0.85615(17) 0.5959(2) 0.18515(15) 0.0213(4) Uani 1 1 d .
H3A H 0.9402 0.6069 0.1608 0.026 Uiso 1 1 calc R
H3B H 0.8357 0.4959 0.1828 0.026 Uiso 1 1 calc R
C4 C 0.85298(16) 0.64640(19) 0.29485(15) 0.0174(4) Uani 1 1 d .
C5 C 0.72154(16) 0.63665(19) 0.33090(14) 0.0160(4) Uani 1 1 d .
C6 C 0.62015(16) 0.67434(18) 0.25719(14) 0.0150(4) Uani 1 1 d .
C7 C 0.49611(16) 0.70088(19) 0.30162(14) 0.0151(4) Uani 1 1 d .
C8 C 0.50708(16) 0.82449(19) 0.37433(14) 0.0165(4) Uani 1 1 d .
C9 C 0.40351(16) 0.8468(2) 0.44006(14) 0.0179(4) Uani 1 1 d .
H9A H 0.4034 0.9254 0.4834 0.021 Uiso 1 1 calc R
C10 C 0.30883(17) 0.7580(2) 0.44000(14) 0.0195(4) Uani 1 1 d .
C11 C 0.30836(16) 0.6313(2) 0.37244(15) 0.0192(4) Uani 1 1 d .
H11A H 0.2532 0.5569 0.3973 0.023 Uiso 1 1 calc R
C12 C 0.27163(16) 0.6779(2) 0.26437(15) 0.0200(4) Uani 1 1 d .
H12A H 0.2079 0.7508 0.2654 0.024 Uiso 1 1 calc R
H12B H 0.2402 0.5987 0.2235 0.024 Uiso 1 1 calc R
C13 C 0.39080(16) 0.7350(2) 0.22135(14) 0.0177(4) Uani 1 1 d .
H13A H 0.3844 0.8364 0.2107 0.021 Uiso 1 1 calc R
H13B H 0.4072 0.6903 0.1557 0.021 Uiso 1 1 calc R
C14 C 0.43908(16) 0.57887(19) 0.36003(15) 0.0183(4) Uani 1 1 d .
H14A H 0.4403 0.4918 0.3203 0.022 Uiso 1 1 calc R
H14B H 0.4818 0.5639 0.4264 0.022 Uiso 1 1 calc R
C15 C 0.19836(17) 0.7835(2) 0.50143(15) 0.0259(5) Uani 1 1 d .
H15A H 0.2081 0.8715 0.5380 0.039 Uiso 1 1 calc R
H15B H 0.1895 0.7077 0.5501 0.039 Uiso 1 1 calc R
H15C H 0.1253 0.7879 0.4564 0.039 Uiso 1 1 calc R
C16 C 0.89041(18) 0.7998(2) 0.30344(17) 0.0243(5) Uani 1 1 d .
H16A H 0.8882 0.8292 0.3743 0.036 Uiso 1 1 calc R
H16B H 0.8334 0.8566 0.2622 0.036 Uiso 1 1 calc R
H16C H 0.9735 0.8115 0.2792 0.036 Uiso 1 1 calc R
C18 C 0.93874(17) 0.5589(2) 0.36261(16) 0.0254(5) Uani 1 1 d .
H18A H 0.9136 0.4615 0.3587 0.038 Uiso 1 1 calc R
H18B H 0.9349 0.5913 0.4328 0.038 Uiso 1 1 calc R
H18C H 1.0227 0.5680 0.3399 0.038 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
C6 C1 C2 125.52(17)
C6 C1 H1A 117.2
C2 C1 H1A 117.2
C1 C2 C3 112.22(16)
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
C2 C3 C4 112.73(16)
C2 C3 H3A 109.0
C4 C3 H3A 109.0
C2 C3 H3B 109.0
C4 C3 H3B 109.0
H3A C3 H3B 107.8
C18 C4 C3 110.22(16)
C18 C4 C5 110.29(16)
C3 C4 C5 109.12(15)
C18 C4 C16 109.36(16)
C3 C4 C16 111.16(16)
C5 C4 C16 106.62(15)
O1 C5 C6 121.76(16)
O1 C5 C4 120.48(16)
C6 C5 C4 117.68(16)
C1 C6 C5 119.33(16)
C1 C6 C7 124.26(16)
C5 C6 C7 116.16(15)
C6 C7 C8 108.79(14)
C6 C7 C14 116.43(15)
C8 C7 C14 107.58(15)
C6 C7 C13 114.64(15)
C8 C7 C13 107.42(14)
C14 C7 C13 101.37(14)
O2 C8 C9 121.86(17)
O2 C8 C7 121.95(16)
C9 C8 C7 116.12(16)
C10 C9 C8 121.12(18)
C10 C9 H9A 119.4
C8 C9 H9A 119.4
C9 C10 C15 122.06(18)
C9 C10 C11 120.11(17)
C15 C10 C11 117.76(16)
C10 C11 C14 110.25(15)
C10 C11 C12 107.89(16)
C14 C11 C12 102.21(15)
C10 C11 H11A 112.0
C14 C11 H11A 112.0
C12 C11 H11A 112.0
C11 C12 C13 104.52(14)
C11 C12 H12A 110.8
C13 C12 H12A 110.8
C11 C12 H12B 110.8
C13 C12 H12B 110.8
H12A C12 H12B 108.9
C12 C13 C7 106.54(15)
C12 C13 H13A 110.4
C7 C13 H13A 110.4
C12 C13 H13B 110.4
C7 C13 H13B 110.4
H13A C13 H13B 108.6
C11 C14 C7 101.32(15)
C11 C14 H14A 111.5
C7 C14 H14A 111.5
C11 C14 H14B 111.5
C7 C14 H14B 111.5
H14A C14 H14B 109.3
C10 C15 H15A 109.5
C10 C15 H15B 109.5
H15A C15 H15B 109.5
C10 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C4 C16 H16A 109.5
C4 C16 H16B 109.5
H16A C16 H16B 109.5
C4 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C4 C18 H18A 109.5
C4 C18 H18B 109.5
H18A C18 H18B 109.5
C4 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C5 1.222(2)
O2 C8 1.228(2)
C1 C6 1.337(3)
C1 C2 1.497(3)
C1 H1A 0.9500
C2 C3 1.521(3)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.531(3)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C18 1.527(3)
C4 C5 1.532(3)
C4 C16 1.538(3)
C5 C6 1.494(2)
C6 C7 1.518(2)
C7 C8 1.533(3)
C7 C14 1.550(3)
C7 C13 1.572(2)
C8 C9 1.467(3)
C9 C10 1.343(3)
C9 H9A 0.9500
C10 C15 1.499(3)
C10 C11 1.513(3)
C11 C14 1.530(3)
C11 C12 1.537(3)
C11 H11A 1.0000
C12 C13 1.541(3)
C12 H12A 0.9900
C12 H12B 0.9900
C13 H13A 0.9900
C13 H13B 0.9900
C14 H14A 0.9900
C14 H14B 0.9900
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
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
C6 C1 C2 C3 13.9(3)
C1 C2 C3 C4 -44.0(2)
C2 C3 C4 C18 177.04(16)
C2 C3 C4 C5 55.8(2)
C2 C3 C4 C16 -61.5(2)
C18 C4 C5 O1 23.1(2)
C3 C4 C5 O1 144.31(18)
C16 C4 C5 O1 -95.5(2)
C18 C4 C5 C6 -160.13(16)
C3 C4 C5 C6 -38.9(2)
C16 C4 C5 C6 81.2(2)
C2 C1 C6 C5 3.3(3)
C2 C1 C6 C7 177.32(17)
O1 C5 C6 C1 -173.02(18)
C4 C5 C6 C1 10.3(2)
O1 C5 C6 C7 12.5(3)
C4 C5 C6 C7 -164.25(15)
C1 C6 C7 C8 -112.4(2)
C5 C6 C7 C8 61.8(2)
C1 C6 C7 C14 125.9(2)
C5 C6 C7 C14 -59.9(2)
C1 C6 C7 C13 7.9(3)
C5 C6 C7 C13 -177.93(15)
C6 C7 C8 O2 15.4(2)
C14 C7 C8 O2 142.36(17)
C13 C7 C8 O2 -109.22(19)
C6 C7 C8 C9 -167.66(15)
C14 C7 C8 C9 -40.7(2)
C13 C7 C8 C9 67.70(19)
O2 C8 C9 C10 -179.07(18)
C7 C8 C9 C10 4.0(3)
C8 C9 C10 C15 -175.97(18)
C8 C9 C10 C11 0.8(3)
C9 C10 C11 C14 32.3(2)
C15 C10 C11 C14 -150.74(17)
C9 C10 C11 C12 -78.5(2)
C15 C10 C11 C12 98.41(19)
C10 C11 C12 C13 81.69(18)
C14 C11 C12 C13 -34.54(19)
C11 C12 C13 C7 7.35(19)
C6 C7 C13 C12 148.36(16)
C8 C7 C13 C12 -90.62(17)
C14 C7 C13 C12 22.09(18)
C10 C11 C14 C7 -65.59(19)
C12 C11 C14 C7 48.92(17)
C6 C7 C14 C11 -168.37(15)
C8 C7 C14 C11 69.30(17)
C13 C7 C14 C11 -43.28(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168334753
