#------------------------------------------------------------------------------
#$Date: 2019-11-11 18:59:08 +0200 (Mon, 11 Nov 2019) $
#$Revision: 226973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/55/4035525.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_4035525
loop_
_publ_author_name
'Novaes, Luiz F. T.'
'Gonçalves, Kaliandra de Almeida'
'Trivella, Daniela B. B.'
'Pastre, Julio C.'
_publ_section_title
;
 Formal Total Synthesis of Actinoranone: Synthesis Approaches and
 Cytotoxic Studies.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5160
_journal_page_last               5176
_journal_paper_doi               10.1021/acs.joc.8b00514
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H33 N O3'
_chemical_formula_sum            'C18 H33 N O3'
_chemical_formula_weight         311.47
_chemical_name_systematic
2-((1R,2S,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)-N-methoxy-N-methylacetamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_Int_Tables_number      4
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-04-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_audit_update_record
;
2017-04-12 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 110.710(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.7535(5)
_cell_length_b                   6.9720(3)
_cell_length_c                   12.6570(6)
_cell_measurement_reflns_used    5258
_cell_measurement_temperature    150
_cell_measurement_theta_max      67.812
_cell_measurement_theta_min      3.733
_cell_volume                     887.62(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.8520
_diffrn_measured_fraction_theta_max 0.8520
_diffrn_measurement_device_type  'Bruker Apex CCD Detector'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6361
_diffrn_reflns_theta_full        67.9856
_diffrn_reflns_theta_max         67.99
_diffrn_reflns_theta_min         3.73
_exptl_absorpt_coefficient_mu    0.614
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1380 before and 0.0483 after correction. The Ratio of minimum to maximum transmission is 0.8525. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.1653
_exptl_crystal_description       needle
_exptl_crystal_F_000             345.0250
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.048
_exptl_crystal_size_min          0.044
_refine_diff_density_max         0.2170
_refine_diff_density_min         -0.2105
_refine_diff_density_rms         0.0650
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.15(17)
_refine_ls_d_res_high            0.8315
_refine_ls_d_res_low             11.8391
_refine_ls_goodness_of_fit_ref   0.9079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    48
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2757
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9079
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1034
_reflns_Friedel_coverage         0.735
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              8
_reflns_limit_k_min              -7
_reflns_limit_l_max              14
_reflns_limit_l_min              -14
_reflns_number_gt                2682
_reflns_number_total             2757
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo8b00514_si_002.cif
_cod_data_source_block           cu_17JAN09_LUIZ_FER_LN223_Cr5_0m
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_database_code               4035525
_olex2_refinement_description
;
;
_olex2_submission_original_sample_id LN223
_olex2_submission_special_instructions 'No special instructions were received'
_publcif_funding_html
;
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,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_refinement_flags_posn
O1 O -0.56349(11) -0.31581(15) -0.26601(9) 0.0293(3) Uani 1.000000 .
H1 H -0.5269(19) -0.2111(10) -0.2399(4) 0.0439(4) Uiso 1.000000 GR
O2 O -0.42565(11) -0.96390(16) -0.19281(9) 0.0299(3) Uani 1.000000 .
O3 O -0.42379(10) -0.84038(16) -0.45868(9) 0.0283(3) Uani 1.000000 .
N1 N -0.37601(13) -0.9135(2) -0.34762(11) 0.0276(3) Uani 1.000000 .
C C -1.03551(17) -0.4660(3) -0.24355(17) 0.0391(4) Uani 1.000000 .
Ha H -1.0045(8) -0.3350(3) -0.2207(9) 0.0586(6) Uiso 1.000000 GR
Hb H -1.0422(12) -0.4870(16) -0.3219(2) 0.0586(6) Uiso 1.000000 GR
Hc H -1.1230(4) -0.4843(16) -0.2373(11) 0.0586(6) Uiso 1.000000 GR
C1 C -0.29997(16) -1.0890(3) -0.33679(14) 0.0317(4) Uani 1.000000 .
H1a H -0.3591(3) -1.1927(5) -0.3774(10) 0.0476(5) Uiso 1.000000 GR
H1b H -0.2302(9) -1.0698(7) -0.3689(11) 0.0476(5) Uiso 1.000000 GR
H1c H -0.2592(12) -1.1231(11) -0.25677(16) 0.0476(5) Uiso 1.000000 GR
C5 C -0.60161(14) -0.6450(2) -0.22776(11) 0.0215(3) Uani 1.000000 .
H5 H -0.57026(14) -0.7419(2) -0.16571(11) 0.0258(4) Uiso 1.000000 R
C6 C -0.73503(15) -0.3803(2) -0.12235(13) 0.0269(3) Uani 1.000000 .
H6a H -0.76184(15) -0.3384(2) -0.05878(13) 0.0323(4) Uiso 1.000000 R
H6b H -0.77187(15) -0.2881(2) -0.18517(13) 0.0323(4) Uiso 1.000000 R
C7 C -0.75687(14) -0.6447(2) -0.26591(12) 0.0230(3) Uani 1.000000 .
C8 C -0.58369(15) -0.3829(2) -0.08497(12) 0.0270(3) Uani 1.000000 .
H8a H -0.54964(15) -0.2514(2) -0.06303(12) 0.0324(4) Uiso 1.000000 R
H8b H -0.54759(15) -0.4657(2) -0.01742(12) 0.0324(4) Uiso 1.000000 R
C9 C -0.53303(14) -0.4557(2) -0.17641(12) 0.0242(3) Uani 1.000000 .
C10 C -0.81929(15) -0.5183(2) -0.37139(13) 0.0292(4) Uani 1.000000 .
H10a H -0.8118(12) -0.3830(3) -0.34896(19) 0.0438(5) Uiso 1.000000 GR
H10b H -0.7725(9) -0.5394(15) -0.4242(5) 0.0438(5) Uiso 1.000000 GR
H10c H -0.9133(4) -0.5520(14) -0.4081(7) 0.0438(5) Uiso 1.000000 GR
C11 C -0.80556(15) -0.8525(2) -0.29408(14) 0.0296(4) Uani 1.000000 .
H11a H -0.79194(15) -0.8920(2) -0.36433(14) 0.0356(4) Uiso 1.000000 R
H11b H -0.75098(15) -0.9377(2) -0.23257(14) 0.0356(4) Uiso 1.000000 R
C12 C -0.44756(14) -0.8725(2) -0.28058(12) 0.0227(3) Uani 1.000000 .
C13 C -0.79043(14) -0.5806(2) -0.16093(12) 0.0234(3) Uani 1.000000 .
H13 H -0.73660(14) -0.6677(2) -0.09882(12) 0.0280(4) Uiso 1.000000 R
C14 C -0.97798(16) -0.8167(3) -0.20306(16) 0.0353(4) Uani 1.000000 .
H14a H -0.92890(16) -0.9037(3) -0.14034(16) 0.0424(5) Uiso 1.000000 R
H14b H -1.07394(16) -0.8312(3) -0.21641(16) 0.0424(5) Uiso 1.000000 R
C16 C -0.38157(15) -0.4801(2) -0.12567(13) 0.0302(4) Uani 1.000000 .
H16a H -0.3475(2) -0.512(2) -0.1858(2) 0.0453(5) Uiso 1.000000 GR
H16b H -0.34091(19) -0.3604(7) -0.0890(11) 0.0453(5) Uiso 1.000000 GR
H16c H -0.35959(16) -0.5838(14) -0.0698(9) 0.0453(5) Uiso 1.000000 GR
C17 C -0.93670(15) -0.6093(2) -0.16653(14) 0.0296(3) Uani 1.000000 .
C18 C -0.95261(16) -0.8796(3) -0.30957(15) 0.0349(4) Uani 1.000000 .
H18a H -1.00860(16) -0.8029(3) -0.37487(15) 0.0419(5) Uiso 1.000000 R
H18b H -0.97730(16) -1.0162(3) -0.32538(15) 0.0419(5) Uiso 1.000000 R
C19 C -0.94207(18) -0.5868(3) -0.04728(16) 0.0392(4) Uani 1.000000 .
H19a H -0.8760(11) -0.6714(16) 0.0052(3) 0.0587(6) Uiso 1.000000 GR
H19b H -0.9227(15) -0.4534(6) -0.0225(5) 0.0587(6) Uiso 1.000000 GR
H19c H -1.0310(5) -0.621(2) -0.0486(3) 0.0587(6) Uiso 1.000000 GR
C20 C -0.33676(16) -0.6925(3) -0.46985(14) 0.0311(3) Uani 1.000000 .
H20a H -0.3608(9) -0.6584(14) -0.54971(18) 0.0466(5) Uiso 1.000000 GR
H20b H -0.3452(10) -0.5793(7) -0.4270(10) 0.0466(5) Uiso 1.000000 GR
H20c H -0.2448(2) -0.7387(7) -0.4405(11) 0.0466(5) Uiso 1.000000 GR
C23 C -0.55023(14) -0.7156(2) -0.32060(12) 0.0246(3) Uani 1.000000 .
H23a H -0.62633(14) -0.7637(2) -0.38542(12) 0.0295(4) Uiso 1.000000 R
H23b H -0.51095(14) -0.6059(2) -0.34742(12) 0.0295(4) Uiso 1.000000 R
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C20 O3 N1 109.75(11)
C1 N1 O3 113.16(11)
C12 N1 O3 117.28(12)
C12 N1 C1 122.77(13)
C9 C5 C7 115.38(11)
C23 C5 C7 113.27(11)
C23 C5 C9 110.35(11)
C13 C6 C8 109.92(12)
C10 C7 C5 110.99(11)
C11 C7 C5 107.97(12)
C11 C7 C10 109.22(12)
C13 C7 C5 106.29(11)
C13 C7 C10 114.40(12)
C13 C7 C11 107.73(12)
C9 C8 C6 113.29(12)
C5 C9 O1 107.81(11)
C8 C9 O1 109.14(12)
C8 C9 C5 111.00(12)
C16 C9 O1 108.44(11)
C16 C9 C5 111.15(13)
C16 C9 C8 109.24(12)
C18 C11 C7 113.35(13)
N1 C12 O2 118.99(14)
C23 C12 O2 124.26(13)
C23 C12 N1 116.76(12)
C7 C13 C6 110.60(12)
C17 C13 C6 113.81(12)
C17 C13 C7 117.21(12)
C18 C14 C17 114.36(14)
C13 C17 C 113.97(13)
C14 C17 C 111.17(15)
C14 C17 C13 108.26(13)
C19 C17 C 107.43(14)
C19 C17 C13 109.21(13)
C19 C17 C14 106.52(14)
C14 C18 C11 110.40(14)
C12 C23 C5 113.06(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.4428(18)
O2 C12 1.2289(19)
O3 N1 1.4102(17)
O3 C20 1.432(2)
N1 C1 1.451(2)
N1 C12 1.3621(19)
C C17 1.531(2)
C5 C7 1.5654(19)
C5 C9 1.539(2)
C5 C23 1.5453(18)
C6 C8 1.526(2)
C6 C13 1.529(2)
C7 C10 1.541(2)
C7 C11 1.539(2)
C7 C13 1.5601(18)
C8 C9 1.530(2)
C9 C16 1.534(2)
C11 C18 1.535(2)
C12 C23 1.509(2)
C13 C17 1.562(2)
C14 C17 1.535(2)
C14 C18 1.531(2)
C17 C19 1.539(2)
