#------------------------------------------------------------------------------
#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/40/1504021.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_1504021
loop_
_publ_author_name
'Saadi, Jakub'
'Lentz, Dieter'
'Reissig, Hans-Ulrich'
_publ_section_title
;
 Medium-sized carbocycles by samarium diiodide-induced carbonyl-alkene
 cyclizations.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3334
_journal_page_last               3337
_journal_paper_doi               10.1021/ol901183h
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C24 H30 O3'
_chemical_formula_weight         366.48
_chemical_melting_point          391.0(10)
_chemical_name_systematic
; 
 Methyl (RaSa,10SR,13SR)-13-Hydroxy-13-isopropyl-10,11,12,13,14,15-
 hexahydro-9H-dibenzo[a,c][11]annulene-10-carboxylate 
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 104.415(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4941(15)
_cell_length_b                   15.472(3)
_cell_length_c                   15.680(3)
_cell_measurement_reflns_used    952
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      30.4
_cell_measurement_theta_min      4.7
_cell_volume                     1995.8(6)
_computing_cell_refinement       'SAINT (Bruker-AXS)'
_computing_data_collection       'SMART (Bruker-AXS)'
_computing_data_reduction        'SAINT (Bruker-AXS)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'SMART CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0133
_diffrn_reflns_av_sigmaI/netI    0.0137
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14292
_diffrn_reflns_theta_full        30.52
_diffrn_reflns_theta_max         30.52
_diffrn_reflns_theta_min         2.63
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.8165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (BRUKER-AXS)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4981
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0315
_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)+(0.0586P)²+0.3933P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0846
_reflns_number_gt                4866
_reflns_number_total             4981
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901183h_si_001.cif
_cod_data_source_block           js290b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '390-392' was changed to '391.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      Cc
_cod_database_code               1504021
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'
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
C1 C 0.70974(11) 0.55340(5) 0.58900(7) 0.01778(17) Uani 1 1 d .
C2 C 0.54480(11) 0.58180(6) 0.60367(7) 0.01796(17) Uani 1 1 d .
H2A H 0.4604 0.5397 0.5749 0.022 Uiso 1 1 calc R
H2B H 0.5511 0.5812 0.6676 0.022 Uiso 1 1 calc R
C3 C 0.49415(12) 0.67236(6) 0.56715(7) 0.01990(18) Uani 1 1 d .
H3A H 0.5253 0.6792 0.5107 0.024 Uiso 1 1 calc R
H3B H 0.5560 0.7156 0.6088 0.024 Uiso 1 1 calc R
C4 C 0.31182(12) 0.69226(6) 0.55145(7) 0.01979(18) Uani 1 1 d .
H4 H 0.2951 0.7533 0.5302 0.024 Uiso 1 1 calc R
C5 C 0.20251(12) 0.63473(6) 0.48077(7) 0.02157(19) Uani 1 1 d .
H5A H 0.2014 0.5755 0.5046 0.026 Uiso 1 1 calc R
H5B H 0.0899 0.6572 0.4677 0.026 Uiso 1 1 calc R
C6 C 0.25689(12) 0.63047(6) 0.39615(7) 0.02241(19) Uani 1 1 d .
C7 C 0.25562(14) 0.70636(7) 0.34652(8) 0.0291(2) Uani 1 1 d .
H7 H 0.2177 0.7586 0.3663 0.035 Uiso 1 1 calc R
C8 C 0.30810(16) 0.70717(8) 0.26965(8) 0.0337(3) Uani 1 1 d .
H8 H 0.3078 0.7595 0.2379 0.040 Uiso 1 1 calc R
C9 C 0.36106(16) 0.63095(8) 0.23953(8) 0.0329(3) Uani 1 1 d .
H9 H 0.3964 0.6307 0.1866 0.040 Uiso 1 1 calc R
C10 C 0.36230(15) 0.55493(7) 0.28696(8) 0.0278(2) Uani 1 1 d .
H10 H 0.3974 0.5028 0.2655 0.033 Uiso 1 1 calc R
C11 C 0.31295(12) 0.55372(6) 0.36551(7) 0.02115(19) Uani 1 1 d .
C12 C 0.31302(12) 0.46976(6) 0.41272(6) 0.01919(18) Uani 1 1 d .
C13 C 0.16327(12) 0.43451(6) 0.41622(7) 0.0228(2) Uani 1 1 d .
H13 H 0.0663 0.4649 0.3894 0.027 Uiso 1 1 calc R
C14 C 0.15240(14) 0.35618(6) 0.45791(8) 0.0245(2) Uani 1 1 d .
H14 H 0.0491 0.3331 0.4587 0.029 Uiso 1 1 calc R
C15 C 0.29336(13) 0.31196(6) 0.49832(7) 0.0233(2) Uani 1 1 d .
H15 H 0.2879 0.2588 0.5278 0.028 Uiso 1 1 calc R
C16 C 0.44220(13) 0.34655(6) 0.49504(7) 0.02088(19) Uani 1 1 d .
H16 H 0.5383 0.3161 0.5231 0.025 Uiso 1 1 calc R
C17 C 0.45700(12) 0.42460(6) 0.45208(6) 0.01849(18) Uani 1 1 d .
C18 C 0.62608(12) 0.45271(6) 0.44752(7) 0.02114(18) Uani 1 1 d .
H18A H 0.6266 0.4552 0.3845 0.025 Uiso 1 1 calc R
H18B H 0.7024 0.4062 0.4745 0.025 Uiso 1 1 calc R
C19 C 0.69740(13) 0.53872(6) 0.48992(7) 0.02050(18) Uani 1 1 d .
H19A H 0.6309 0.5862 0.4569 0.025 Uiso 1 1 calc R
H19B H 0.8080 0.5447 0.4807 0.025 Uiso 1 1 calc R
C20 C 0.77843(12) 0.47262(6) 0.64460(7) 0.02010(18) Uani 1 1 d .
H20 H 0.7014 0.4237 0.6238 0.024 Uiso 1 1 calc R
C21 C 0.94515(13) 0.44539(7) 0.63279(9) 0.0305(2) Uani 1 1 d .
H21A H 0.9755 0.3894 0.6615 0.046 Uiso 1 1 calc R
H21B H 1.0264 0.4889 0.6595 0.046 Uiso 1 1 calc R
H21C H 0.9401 0.4404 0.5699 0.046 Uiso 1 1 calc R
C22 C 0.79097(16) 0.48546(7) 0.74306(8) 0.0311(2) Uani 1 1 d .
H22A H 0.8407 0.5417 0.7618 0.047 Uiso 1 1 calc R
H22B H 0.8582 0.4395 0.7767 0.047 Uiso 1 1 calc R
H22C H 0.6820 0.4834 0.7536 0.047 Uiso 1 1 calc R
C23 C 0.25735(12) 0.68688(6) 0.63617(7) 0.02163(19) Uani 1 1 d .
C24 C 0.29243(19) 0.74315(8) 0.77919(9) 0.0355(3) Uani 1 1 d .
H24A H 0.3034 0.6843 0.8029 0.053 Uiso 1 1 calc R
H24B H 0.1799 0.7627 0.7711 0.053 Uiso 1 1 calc R
H24C H 0.3653 0.7819 0.8204 0.053 Uiso 1 1 calc R
O1 O 0.81451(9) 0.62652(4) 0.61765(6) 0.02410(16) Uani 1 1 d .
H1 H 0.9102 0.6136 0.6168 0.036 Uiso 1 1 calc R
O2 O 0.15927(12) 0.63680(7) 0.65078(8) 0.0416(2) Uani 1 1 d .
O3 O 0.33460(13) 0.74412(5) 0.69556(6) 0.0342(2) Uani 1 1 d .
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
O1 C1 C2 104.12(7)
O1 C1 C19 108.10(8)
C2 C1 C19 110.81(8)
O1 C1 C20 109.91(8)
C2 C1 C20 112.00(8)
C19 C1 C20 111.57(7)
C3 C2 C1 112.70(8)
C2 C3 C4 114.85(8)
C23 C4 C3 111.36(8)
C23 C4 C5 109.80(8)
C3 C4 C5 113.73(8)
C6 C5 C4 113.33(8)
C7 C6 C11 118.15(11)
C7 C6 C5 119.16(10)
C11 C6 C5 122.67(8)
C8 C7 C6 121.93(11)
C7 C8 C9 119.39(10)
C8 C9 C10 119.82(12)
C9 C10 C11 121.28(11)
C10 C11 C6 119.41(9)
C10 C11 C12 119.01(9)
C6 C11 C12 121.50(9)
C13 C12 C17 119.21(9)
C13 C12 C11 118.05(9)
C17 C12 C11 122.72(9)
C14 C13 C12 121.74(10)
C15 C14 C13 119.57(10)
C16 C15 C14 118.96(9)
C15 C16 C17 122.80(9)
C16 C17 C12 117.70(9)
C16 C17 C18 117.88(8)
C12 C17 C18 124.37(8)
C17 C18 C19 120.07(8)
C18 C19 C1 118.73(8)
C21 C20 C22 108.82(9)
C21 C20 C1 112.52(8)
C22 C20 C1 112.54(8)
O2 C23 O3 122.65(11)
O2 C23 C4 125.52(10)
O3 C23 C4 111.81(9)
C23 O3 C24 115.94(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.4403(11)
C1 C2 1.5393(13)
C1 C19 1.5475(15)
C1 C20 1.5522(12)
C2 C3 1.5342(12)
C3 C4 1.5376(14)
C4 C23 1.5138(15)
C4 C5 1.5396(14)
C5 C6 1.5111(16)
C6 C7 1.4072(13)
C6 C11 1.4075(14)
C7 C8 1.3854(19)
C8 C9 1.386(2)
C9 C10 1.3902(15)
C10 C11 1.3965(16)
C11 C12 1.4950(13)
C12 C13 1.3975(14)
C12 C17 1.4103(13)
C13 C14 1.3909(14)
C14 C15 1.3877(15)
C15 C16 1.3856(15)
C16 C17 1.4035(13)
C17 C18 1.5193(14)
C18 C19 1.5424(14)
C20 C21 1.5323(15)
C20 C22 1.5338(17)
C23 O2 1.2007(14)
C23 O3 1.3334(14)
C24 O3 1.4430(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101490132
