#------------------------------------------------------------------------------
#$Date: 2025-08-20 11:41:31 +0200 (Wed 20 de Aug de 2025) $
#$Revision: 301828 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/49/4034930.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_4034930
loop_
_publ_author_name
'Matías, Desirée M'
'Johnson, Jeffrey S.'
_publ_section_title
;
 Synthesis and Desymmetrization of meso Tricyclic Systems Derived from
 Benzene Oxide.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4859
_journal_page_last               4866
_journal_paper_doi               10.1021/acs.joc.8b00523
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C18 H29 N O5'
_chemical_formula_sum            'C18 H29 N O5'
_chemical_formula_weight         339.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-02-08
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   5.79580(6)
_cell_length_b                   14.35143(15)
_cell_length_c                   43.7743(5)
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.53
_cell_measurement_theta_min      3.03
_cell_volume                     3641.06(7)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            40425
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.599
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_min         2.018
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_correction_T_min  0.8756
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0542 before and 0.0435 after correction.
The Ratio of minimum to maximum transmission is 0.8852.
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    1.238
_exptl_crystal_description       plate
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.262
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3201
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0573P)²+1.5450P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1242
_refine_ls_wR_factor_ref         0.1336
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2516
_reflns_number_total             3201
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo8b00523_si_001.cif
_cod_data_source_block           x1602003
_cod_database_code               4034930
_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   0.974
_shelx_estimated_absorpt_t_min   0.831
_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:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B),
 C8(H8A,H8B), C19(H19A,H19B), C22(H22A,H22B)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
C1 C 0.2417(7) 1.1906(3) 0.58453(6) 0.1030(11) Uani 1 1 d .
H1A H 0.0755 1.2027 0.5834 0.155 Uiso 1 1 calc GR
H1B H 0.3145 1.2365 0.5980 0.155 Uiso 1 1 calc GR
H1C H 0.2679 1.1278 0.5926 0.155 Uiso 1 1 calc GR
C2 C 0.3441(6) 1.1979(3) 0.55333(7) 0.1044(12) Uani 1 1 d .
H2A H 0.3228 1.2624 0.5458 0.125 Uiso 1 1 calc R
H2B H 0.5121 1.1863 0.5548 0.125 Uiso 1 1 calc R
C3 C 0.2446(6) 1.1324(2) 0.53053(6) 0.0902(9) Uani 1 1 d .
H3A H 0.0751 1.1407 0.5302 0.108 Uiso 1 1 calc R
H3B H 0.2765 1.0679 0.5373 0.108 Uiso 1 1 calc R
C4 C 0.3359(6) 1.1442(2) 0.49801(5) 0.0819(9) Uani 1 1 d .
H4A H 0.3173 1.2102 0.4918 0.098 Uiso 1 1 calc R
H4B H 0.5029 1.1298 0.4978 0.098 Uiso 1 1 calc R
C5 C 0.2164(5) 1.08336(19) 0.47507(5) 0.0756(8) Uani 1 1 d .
H5A H 0.0479 1.0933 0.4768 0.091 Uiso 1 1 calc R
H5B H 0.2481 1.0174 0.4802 0.091 Uiso 1 1 calc R
C6 C 0.2886(5) 1.10073(19) 0.44203(5) 0.0673(7) Uani 1 1 d .
H6A H 0.2681 1.1676 0.4372 0.081 Uiso 1 1 calc R
H6B H 0.4544 1.0858 0.4397 0.081 Uiso 1 1 calc R
C7 C 0.1509(5) 1.04317(18) 0.41936(5) 0.0661(7) Uani 1 1 d .
H7A H 0.1814 0.9762 0.4231 0.079 Uiso 1 1 calc R
H7B H -0.0157 1.0543 0.4227 0.079 Uiso 1 1 calc R
C8 C 0.2100(4) 1.06614(17) 0.38664(5) 0.0607(6) Uani 1 1 d .
H8A H 0.1682 1.1318 0.3824 0.073 Uiso 1 1 calc R
H8B H 0.3786 1.0596 0.3836 0.073 Uiso 1 1 calc R
N9 N 0.0892(3) 1.00535(13) 0.36501(4) 0.0516(5) Uani 1 1 d .
C10 C 0.1588(4) 0.91547(17) 0.35915(5) 0.0524(6) Uani 1 1 d .
C11 C -0.0139(3) 0.86965(14) 0.33781(4) 0.0429(5) Uani 1 1 d .
H11 H -0.1022 0.8222 0.3498 0.052 Uiso 1 1 calc R
C12 C 0.1071(3) 0.81931(13) 0.31131(4) 0.0393(4) Uani 1 1 d .
H12 H 0.2368 0.8602 0.3044 0.047 Uiso 1 1 calc R
C13 C -0.0539(3) 0.80798(13) 0.28466(4) 0.0401(4) Uani 1 1 d .
H13 H 0.0013 0.7679 0.2675 0.048 Uiso 1 1 calc R
C14 C -0.2003(3) 0.88644(13) 0.27653(4) 0.0415(5) Uani 1 1 d .
H14 H -0.2353 0.8945 0.2543 0.050 Uiso 1 1 calc R
C15 C -0.1796(3) 0.97424(14) 0.29514(4) 0.0409(5) Uani 1 1 d .
H15 H -0.0238 1.0009 0.2906 0.049 Uiso 1 1 calc R
C16 C -0.1813(3) 0.94956(13) 0.32936(4) 0.0417(5) Uani 1 1 d .
H16 H -0.3413 0.9304 0.3352 0.050 Uiso 1 1 calc R
C17 C -0.1094(4) 1.03014(16) 0.34950(5) 0.0504(5) Uani 1 1 d .
O18 O 0.3315(3) 0.88123(14) 0.36985(4) 0.0755(5) Uani 1 1 d .
C19 C 0.2127(4) 0.72727(14) 0.32157(5) 0.0496(5) Uani 1 1 d .
H19A H 0.3276 0.7393 0.3378 0.060 Uiso 1 1 calc R
H19B H 0.0903 0.6871 0.3302 0.060 Uiso 1 1 calc R
O20 O 0.3221(3) 0.67976(11) 0.29677(4) 0.0564(4) Uani 1 1 d .
H20 H 0.446(6) 0.710(2) 0.2927(6) 0.096(11) Uiso 1 1 d .
O21 O -0.2994(2) 0.80520(10) 0.29133(3) 0.0498(4) Uani 1 1 d .
C22 C -0.3538(3) 1.04730(14) 0.28592(5) 0.0480(5) Uani 1 1 d .
H22A H -0.3257 1.1054 0.2975 0.058 Uiso 1 1 calc R
H22B H -0.3374 1.0614 0.2639 0.058 Uiso 1 1 calc R
O23 O -0.5805(3) 1.01413(11) 0.29196(4) 0.0604(5) Uani 1 1 d .
H23 H -0.667(5) 1.063(2) 0.2917(6) 0.089(10) Uiso 1 1 d .
O24 O -0.2032(3) 1.10497(12) 0.35223(4) 0.0720(5) 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 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C3 C2 C1 114.6(3)
C2 C3 C4 114.9(3)
C5 C4 C3 113.6(2)
C4 C5 C6 114.4(2)
C7 C6 C5 112.8(2)
C8 C7 C6 112.5(2)
N9 C8 C7 111.99(19)
C10 N9 C8 122.59(19)
C10 N9 C17 113.18(18)
C17 N9 C8 124.2(2)
N9 C10 C11 109.12(18)
O18 C10 N9 123.5(2)
O18 C10 C11 127.4(2)
C10 C11 C12 111.53(16)
C10 C11 C16 103.85(16)
C12 C11 C16 117.03(15)
C13 C12 C11 110.70(16)
C13 C12 C19 112.60(16)
C19 C12 C11 111.63(16)
C14 C13 C12 117.94(17)
O21 C13 C12 117.08(16)
O21 C13 C14 59.94(12)
C13 C14 C15 118.00(16)
O21 C14 C13 60.00(12)
O21 C14 C15 117.54(16)
C14 C15 C16 109.48(16)
C14 C15 C22 112.54(16)
C22 C15 C16 114.54(16)
C15 C16 C11 113.52(15)
C17 C16 C11 104.75(16)
C17 C16 C15 112.92(16)
N9 C17 C16 108.59(18)
O24 C17 N9 123.6(2)
O24 C17 C16 127.8(2)
O20 C19 C12 111.57(17)
C14 O21 C13 60.06(12)
O23 C22 C15 109.59(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.493(4)
C2 C3 1.487(4)
C3 C4 1.528(4)
C4 C5 1.500(3)
C5 C6 1.526(3)
C6 C7 1.518(3)
C7 C8 1.509(3)
C8 N9 1.466(3)
N9 C10 1.376(3)
N9 C17 1.383(3)
C10 C11 1.519(3)
C10 O18 1.210(3)
C11 C12 1.536(3)
C11 C16 1.547(3)
C12 C13 1.503(3)
C12 C19 1.523(3)
C13 C14 1.454(3)
C13 O21 1.453(2)
C14 C15 1.505(3)
C14 O21 1.452(2)
C15 C16 1.539(3)
C15 C22 1.511(3)
C16 C17 1.513(3)
C17 O24 1.210(3)
C19 O20 1.430(3)
C22 O23 1.423(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168328759
