#------------------------------------------------------------------------------
#$Date: 2020-11-21 00:55:45 +0200 (Sat, 21 Nov 2020) $
#$Revision: 259207 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/82/4518257.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_4518257
loop_
_publ_author_name
'Clanton, Nicholas A.'
'Hastings, Shayne D.'
'Foultz, Griffin B.'
'Contreras, Julie A.'
'Yee, Samantha S.'
'Arman, Hadi D.'
'Risinger, April L.'
'Frantz, Doug E.'
_publ_section_title
;
 Synthesis and Biological Evaluations of Electrophilic Steroids Inspired
 by the Taccalonolides
;
_journal_name_full               'ACS Medicinal Chemistry Letters'
_journal_paper_doi               10.1021/acsmedchemlett.0c00534
_journal_year                    2020
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C19 H26 O2'
_chemical_formula_sum            'C19 H26 O2'
_chemical_formula_weight         286.40
_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_Hall           'P 4w'
_space_group_name_H-M_alt        'P 41'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1412(2)
_cell_length_b                   9.1412(2)
_cell_length_c                   18.5205(6)
_cell_measurement_reflns_used    4956
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      28.8380
_cell_measurement_theta_min      3.1090
_cell_volume                     1547.60(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28e (Rigaku OD, 2015)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      98(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -97.00  20.00   1.00   25.00    --   -7.70 -30.00 -36.00  117
  2  ω    -85.00  26.00   1.00   25.00    --    4.20 -38.00  90.00  111
  3  ω    -32.00  82.00   1.00   25.00    --   -7.70  38.00-120.00  114
  4  ω    -45.00 -20.00   1.00   25.00    --   -7.70  19.00  30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0072655000
_diffrn_orient_matrix_UB_12      0.0740227000
_diffrn_orient_matrix_UB_13      0.0108797000
_diffrn_orient_matrix_UB_21      0.0734001000
_diffrn_orient_matrix_UB_22      -0.0134686000
_diffrn_orient_matrix_UB_23      0.0105328000
_diffrn_orient_matrix_UB_31      0.0241842000
_diffrn_orient_matrix_UB_32      0.0188382000
_diffrn_orient_matrix_UB_33      -0.0351789000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16652
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.993
_diffrn_reflns_theta_min         2.485
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;

;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3010
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0446
_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)+(0.0380P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.0990
_reflns_Friedel_coverage         0.927
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                2975
_reflns_number_total             3010
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ml0c00534_si_004.cif
_cod_data_source_block           cd1830
_cod_original_cell_volume        1547.60(8)
_cod_database_code               4518257
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C19H26O2
_chemical_oxdiff_usercomment     NAC-224-90
_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   0.995
_shelx_estimated_absorpt_t_min   0.975
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C15(H15), C6(H6), C17(H17), C1(H1), C16(H16), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C4(H4A,H4B), C13(H13A,H13B), C5(H5A,H5B), C8(H8A,H8B),
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C)
;
_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.073
_oxdiff_exptl_absorpt_empirical_full_min 0.966
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'
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 0.4469(2) 0.5340(2) 0.58440(12) 0.0210(5) Uani 1 1 d . . . . .
O2 O 0.1451(2) 0.4597(2) 0.47152(13) 0.0245(5) Uani 1 1 d . . . . .
C15 C 0.6223(3) 0.2353(3) 0.50728(15) 0.0113(6) Uani 1 1 d . . . . .
H15 H 0.609913 0.205553 0.558888 0.014 Uiso 1 1 calc R . . . .
C7 C 0.6960(3) -0.0278(3) 0.47346(15) 0.0125(6) Uani 1 1 d . . . . .
C6 C 0.5903(3) 0.1016(3) 0.45757(15) 0.0113(6) Uani 1 1 d . . . . .
H6 H 0.613854 0.134667 0.407432 0.014 Uiso 1 1 calc R . . . .
C14 C 0.7790(3) 0.2871(3) 0.49522(16) 0.0136(6) Uani 1 1 d . . . . .
H14A H 0.790176 0.321176 0.444778 0.016 Uiso 1 1 calc R . . . .
H14B H 0.799969 0.370676 0.527625 0.016 Uiso 1 1 calc R . . . .
C17 C 0.5183(3) 0.5078(3) 0.51641(17) 0.0160(6) Uani 1 1 d . . . . .
H17 H 0.600906 0.572277 0.500893 0.019 Uiso 1 1 calc R . . . .
C4 C 0.3187(3) 0.1832(3) 0.44697(17) 0.0157(6) Uani 1 1 d . . . . .
H4A H 0.327505 0.225033 0.397854 0.019 Uiso 1 1 calc R . . . .
H4B H 0.217418 0.147009 0.453224 0.019 Uiso 1 1 calc R . . . .
C1 C 0.3677(3) 0.5664(3) 0.51825(17) 0.0195(7) Uani 1 1 d . . . . .
H1 H 0.347292 0.669832 0.503835 0.023 Uiso 1 1 calc R . . . .
C13 C 0.8879(3) 0.1645(3) 0.50994(17) 0.0168(6) Uani 1 1 d . . . . .
H13A H 0.884181 0.138332 0.561783 0.020 Uiso 1 1 calc R . . . .
H13B H 0.987923 0.199479 0.499023 0.020 Uiso 1 1 calc R . . . .
C5 C 0.4276(3) 0.0556(3) 0.45591(17) 0.0165(6) Uani 1 1 d . . . . .
H5A H 0.413084 -0.014046 0.415604 0.020 Uiso 1 1 calc R . . . .
H5B H 0.404581 0.003328 0.501326 0.020 Uiso 1 1 calc R . . . .
C16 C 0.5099(3) 0.3514(3) 0.48867(15) 0.0136(6) Uani 1 1 d . . . . .
H16 H 0.516150 0.361090 0.434979 0.016 Uiso 1 1 calc R . . . .
C19 C 0.6713(3) -0.0922(3) 0.54915(16) 0.0159(6) Uani 1 1 d . . . . .
H19A H 0.694877 -0.018263 0.585675 0.024 Uiso 1 1 calc GR . . . .
H19B H 0.734480 -0.177700 0.555813 0.024 Uiso 1 1 calc GR . . . .
H19C H 0.568693 -0.121547 0.554229 0.024 Uiso 1 1 calc GR . . . .
C18 C 0.3181(3) 0.2419(3) 0.57913(16) 0.0179(7) Uani 1 1 d . . . . .
H18A H 0.217269 0.205514 0.580963 0.027 Uiso 1 1 calc GR . . . .
H18B H 0.330222 0.320792 0.614444 0.027 Uiso 1 1 calc GR . . . .
H18C H 0.385736 0.161998 0.590509 0.027 Uiso 1 1 calc GR . . . .
C3 C 0.3509(3) 0.3006(3) 0.50287(15) 0.0144(6) Uani 1 1 d . . . . .
C2 C 0.2673(3) 0.4444(3) 0.49526(15) 0.0170(6) Uani 1 1 d . . . . .
C12 C 0.8556(3) 0.0281(3) 0.46457(16) 0.0143(6) Uani 1 1 d . . . . .
H12 H 0.867261 0.057121 0.412830 0.017 Uiso 1 1 calc R . . . .
C8 C 0.6731(3) -0.1497(3) 0.41671(16) 0.0158(6) Uani 1 1 d . . . . .
H8A H 0.578806 -0.199332 0.426224 0.019 Uiso 1 1 calc R . . . .
H8B H 0.667559 -0.104964 0.368114 0.019 Uiso 1 1 calc R . . . .
C10 C 0.9248(4) -0.2375(3) 0.44610(17) 0.0206(7) Uani 1 1 d . . . . .
H10 H 0.994676 -0.314472 0.445754 0.025 Uiso 1 1 calc R . . . .
C9 C 0.7944(3) -0.2618(3) 0.41749(18) 0.0193(6) Uani 1 1 d . . . . .
H9 H 0.776181 -0.354731 0.396332 0.023 Uiso 1 1 calc R . . . .
C11 C 0.9671(3) -0.0936(3) 0.47909(18) 0.0198(7) Uani 1 1 d . . . . .
H11A H 1.063347 -0.063356 0.459578 0.024 Uiso 1 1 calc R . . . .
H11B H 0.977926 -0.106273 0.531906 0.024 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
C17 O1 C1 61.46(19) . . ?
C6 C15 H15 109.3 . . ?
C14 C15 H15 109.3 . . ?
C14 C15 C6 109.5(2) . . ?
C16 C15 H15 109.3 . . ?
C16 C15 C6 106.7(2) . . ?
C16 C15 C14 112.7(2) . . ?
C19 C7 C6 111.8(2) . . ?
C19 C7 C12 111.1(2) . . ?
C19 C7 C8 108.9(2) . . ?
C12 C7 C6 108.2(2) . . ?
C8 C7 C6 109.6(2) . . ?
C8 C7 C12 107.0(2) . . ?
C15 C6 H6 105.7 . . ?
C7 C6 C15 111.6(2) . . ?
C7 C6 H6 105.7 . . ?
C5 C6 C15 114.0(2) . . ?
C5 C6 C7 113.2(2) . . ?
C5 C6 H6 105.7 . . ?
C15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C13 C14 C15 111.0(2) . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
O1 C17 H17 119.7 . . ?
O1 C17 C1 59.78(19) . . ?
O1 C17 C16 115.4(2) . . ?
C1 C17 H17 119.7 . . ?
C1 C17 C16 107.5(2) . . ?
C16 C17 H17 119.7 . . ?
H4A C4 H4B 108.2 . . ?
C5 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
C3 C4 C5 109.6(2) . . ?
O1 C1 C17 58.76(19) . . ?
O1 C1 H1 120.7 . . ?
O1 C1 C2 113.0(2) . . ?
C17 C1 H1 120.7 . . ?
C17 C1 C2 107.0(3) . . ?
C2 C1 H1 120.7 . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
C14 C13 C12 112.0(2) . . ?
H13A C13 H13B 107.9 . . ?
C12 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
C6 C5 H5A 108.6 . . ?
C6 C5 H5B 108.6 . . ?
C4 C5 C6 114.7(2) . . ?
C4 C5 H5A 108.6 . . ?
C4 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
C15 C16 C17 123.1(2) . . ?
C15 C16 H16 104.4 . . ?
C15 C16 C3 112.8(2) . . ?
C17 C16 H16 104.4 . . ?
C17 C16 C3 105.8(2) . . ?
C3 C16 H16 104.4 . . ?
C7 C19 H19A 109.5 . . ?
C7 C19 H19B 109.5 . . ?
C7 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
C4 C3 C16 106.1(2) . . ?
C4 C3 C18 109.9(2) . . ?
C4 C3 C2 116.6(2) . . ?
C18 C3 C16 116.3(2) . . ?
C2 C3 C16 101.3(2) . . ?
C2 C3 C18 106.7(2) . . ?
O2 C2 C1 125.5(3) . . ?
O2 C2 C3 126.6(3) . . ?
C1 C2 C3 107.8(2) . . ?
C7 C12 H12 106.8 . . ?
C13 C12 C7 113.0(2) . . ?
C13 C12 H12 106.8 . . ?
C13 C12 C11 111.5(2) . . ?
C11 C12 C7 111.5(2) . . ?
C11 C12 H12 106.8 . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 C7 112.5(2) . . ?
C9 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C9 C10 H10 118.6 . . ?
C9 C10 C11 122.8(3) . . ?
C11 C10 H10 118.6 . . ?
C8 C9 H9 118.3 . . ?
C10 C9 C8 123.5(3) . . ?
C10 C9 H9 118.3 . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C10 C11 C12 113.1(3) . . ?
C10 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
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 C17 1.438(4) . ?
O1 C1 1.454(4) . ?
O2 C2 1.209(4) . ?
C15 H15 1.0000 . ?
C15 C6 1.558(4) . ?
C15 C14 1.525(4) . ?
C15 C16 1.517(4) . ?
C7 C6 1.556(4) . ?
C7 C19 1.537(4) . ?
C7 C12 1.554(4) . ?
C7 C8 1.546(4) . ?
C6 H6 1.0000 . ?
C6 C5 1.545(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C13 1.524(4) . ?
C17 H17 1.0000 . ?
C17 C1 1.478(4) . ?
C17 C16 1.521(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.543(4) . ?
C4 C3 1.520(4) . ?
C1 H1 1.0000 . ?
C1 C2 1.506(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C12 1.532(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C16 H16 1.0000 . ?
C16 C3 1.548(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 C3 1.540(4) . ?
C3 C2 1.528(4) . ?
C12 H12 1.0000 . ?
C12 C11 1.533(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.510(4) . ?
C10 H10 0.9500 . ?
C10 C9 1.323(5) . ?
C10 C11 1.502(5) . ?
C9 H9 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
