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#$Date: 2025-08-18 16:30:32 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301775 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/32/1503296.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_1503296
loop_
_publ_author_name
'Garnsey, Michelle R.'
'Lim, Daniel'
'Yost, Julianne M.'
'Coltart, Don M.'
_publ_section_title
;
 Development of a strategy for the asymmetric synthesis of polycyclic
 polyprenylated acylphloroglucinols via N-amino cyclic carbamate
 hydrazones: application to the total synthesis of (+)-clusianone.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5234
_journal_page_last               5237
_journal_paper_doi               10.1021/ol1022728
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C18 H22 N2 O2'
_chemical_formula_sum            'C18 H22 N2 O2'
_chemical_formula_weight         298.38
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.1021(2)
_cell_length_b                   9.1077(2)
_cell_length_c                   22.0686(5)
_cell_measurement_reflns_used    9614
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      33.0
_cell_measurement_theta_min      2.2
_cell_volume                     1628.48(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker platform with Smart6000 CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         ' sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            24123
_diffrn_reflns_theta_full        33.36
_diffrn_reflns_theta_max         33.36
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'sadabs (Sheldrick, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular cuboid'
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         5934
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0395
_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)+(0.0699P)²+0.0227P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1004
_reflns_number_gt                5469
_reflns_number_total             5934
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol1022728_si_004.cif
_cod_data_source_block           sad
_cod_original_sg_symbol_H-M      'P21 21 21'
_cod_database_code               1503296
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
O1 O 0.19135(8) 0.78974(8) 0.19495(3) 0.03073(15) Uani 1 1 d
O2 O 0.05461(9) 0.75330(8) 0.10718(3) 0.03070(14) Uani 1 1 d
N1 N -0.08159(9) 0.75513(8) 0.19986(3) 0.02262(13) Uani 1 1 d
N2 N -0.21561(9) 0.66515(8) 0.18092(3) 0.02284(14) Uani 1 1 d
C1 C 0.14647(11) 0.79508(10) 0.25867(4) 0.02624(16) Uani 1 1 d
C2 C -0.02477(10) 0.72532(9) 0.26163(4) 0.02254(15) Uani 1 1 d
C3 C -0.13854(12) 0.79085(10) 0.30946(4) 0.02681(17) Uani 1 1 d
C4 C -0.07363(11) 0.76008(10) 0.37239(4) 0.02458(15) Uani 1 1 d
C5 C 0.02004(14) 0.86454(11) 0.40325(5) 0.03173(19) Uani 1 1 d
C6 C 0.09032(15) 0.83057(13) 0.45917(5) 0.0368(2) Uani 1 1 d
C7 C 0.06711(15) 0.69349(13) 0.48472(5) 0.0379(2) Uani 1 1 d
C8 C -0.02819(15) 0.58962(12) 0.45483(5) 0.0349(2) Uani 1 1 d
C9 C -0.09799(12) 0.62267(10) 0.39900(4) 0.02851(17) Uani 1 1 d
C10 C 0.05351(10) 0.76381(10) 0.16153(4) 0.02499(16) Uani 1 1 d
C11 C -0.31516(10) 0.72488(9) 0.14225(4) 0.02127(14) Uani 1 1 d
C12 C -0.31104(11) 0.88287(10) 0.12088(4) 0.02437(16) Uani 1 1 d
C13 C -0.37209(12) 0.89285(11) 0.05557(4) 0.02911(18) Uani 1 1 d
C14 C -0.54330(12) 0.82545(12) 0.04781(4) 0.02918(18) Uani 1 1 d
C15 C -0.55652(11) 0.68032(10) 0.07882(4) 0.02592(16) Uani 1 1 d
C16 C -0.45117(10) 0.63058(9) 0.12113(4) 0.02269(15) Uani 1 1 d
C17 C -0.41616(15) 0.97553(11) 0.16459(5) 0.0342(2) Uani 1 1 d
C18 C -0.46900(13) 0.47991(12) 0.14839(5) 0.0318(2) Uani 1 1 d
H1A H 0.140(2) 0.8963(17) 0.2730(7) 0.044(4) Uiso 1 1 d
H1B H 0.2361(17) 0.7479(15) 0.2790(6) 0.031(3) Uiso 1 1 d
H2 H -0.0077(17) 0.6257(16) 0.2683(6) 0.035(4) Uiso 1 1 d
H3A H -0.243(2) 0.7474(17) 0.3040(7) 0.039(4) Uiso 1 1 d
H3B H -0.1464(17) 0.8974(14) 0.3027(6) 0.026(3) Uiso 1 1 d
H5 H 0.035(2) 0.9587(18) 0.3876(7) 0.046(4) Uiso 1 1 d
H6 H 0.153(3) 0.908(2) 0.4791(9) 0.067(5) Uiso 1 1 d
H7 H 0.115(3) 0.674(2) 0.5220(9) 0.062(5) Uiso 1 1 d
H8 H -0.043(2) 0.488(2) 0.4724(9) 0.063(5) Uiso 1 1 d
H9 H -0.162(2) 0.5481(18) 0.3777(7) 0.042(4) Uiso 1 1 d
H12 H -0.2019(17) 0.9175(14) 0.1223(6) 0.025(3) Uiso 1 1 d
H13A H -0.3707(19) 0.9951(15) 0.0412(6) 0.033(3) Uiso 1 1 d
H13B H -0.2942(17) 0.8302(16) 0.0289(6) 0.034(3) Uiso 1 1 d
H14A H -0.567(2) 0.8172(17) 0.0059(8) 0.051(4) Uiso 1 1 d
H14B H -0.630(2) 0.8929(17) 0.0631(7) 0.044(4) Uiso 1 1 d
H15 H -0.6504(17) 0.6202(14) 0.0699(6) 0.029(3) Uiso 1 1 d
H17A H -0.366(2) 0.9788(16) 0.2057(7) 0.043(4) Uiso 1 1 d
H17B H -0.420(2) 1.0706(18) 0.1497(7) 0.044(4) Uiso 1 1 d
H17C H -0.527(2) 0.9329(18) 0.1677(7) 0.044(4) Uiso 1 1 d
H18A H -0.472(2) 0.4892(16) 0.1929(7) 0.040(4) Uiso 1 1 d
H18B H -0.373(2) 0.4139(16) 0.1361(6) 0.038(4) Uiso 1 1 d
H18C H -0.566(2) 0.436(2) 0.1334(8) 0.058(5) Uiso 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'
N N 0.0061 0.0033 '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
C10 O1 C1 108.99(7)
C10 N1 N2 117.14(7)
C10 N1 C2 109.31(7)
N2 N1 C2 113.99(7)
C11 N2 N1 115.29(7)
O1 C1 C2 104.76(7)
O1 C1 H1A 111.0(9)
C2 C1 H1A 109.5(10)
O1 C1 H1B 104.4(8)
C2 C1 H1B 118.9(8)
H1A C1 H1B 108.1(12)
N1 C2 C3 112.47(7)
N1 C2 C1 99.71(7)
C3 C2 C1 114.60(7)
N1 C2 H2 112.0(9)
C3 C2 H2 111.3(9)
C1 C2 H2 106.1(9)
C4 C3 C2 110.71(7)
C4 C3 H3A 110.7(9)
C2 C3 H3A 106.9(10)
C4 C3 H3B 110.1(7)
C2 C3 H3B 108.7(8)
H3A C3 H3B 109.6(13)
C5 C4 C9 118.87(8)
C5 C4 C3 120.78(8)
C9 C4 C3 120.23(8)
C6 C5 C4 120.22(10)
C6 C5 H5 118.6(10)
C4 C5 H5 121.2(10)
C7 C6 C5 120.39(10)
C7 C6 H6 122.6(11)
C5 C6 H6 117.0(11)
C6 C7 C8 119.82(10)
C6 C7 H7 118.7(12)
C8 C7 H7 121.5(12)
C7 C8 C9 120.03(10)
C7 C8 H8 120.3(11)
C9 C8 H8 119.6(11)
C8 C9 C4 120.66(9)
C8 C9 H9 119.6(9)
C4 C9 H9 119.7(9)
O2 C10 O1 123.29(8)
O2 C10 N1 127.58(8)
O1 C10 N1 109.12(8)
N2 C11 C16 115.45(7)
N2 C11 C12 126.22(8)
C16 C11 C12 118.17(7)
C11 C12 C13 110.09(7)
C11 C12 C17 108.28(7)
C13 C12 C17 112.32(8)
C11 C12 H12 109.2(8)
C13 C12 H12 108.5(8)
C17 C12 H12 108.4(8)
C12 C13 C14 112.11(7)
C12 C13 H13A 110.9(8)
C14 C13 H13A 110.8(9)
C12 C13 H13B 107.9(8)
C14 C13 H13B 105.6(8)
H13A C13 H13B 109.4(12)
C15 C14 C13 111.72(8)
C15 C14 H14A 111.3(9)
C13 C14 H14A 108.9(10)
C15 C14 H14B 109.9(9)
C13 C14 H14B 110.9(9)
H14A C14 H14B 103.8(14)
C16 C15 C14 124.87(8)
C16 C15 H15 117.0(8)
C14 C15 H15 118.0(8)
C15 C16 C11 119.90(8)
C15 C16 C18 121.61(8)
C11 C16 C18 118.49(7)
C12 C17 H17A 111.2(10)
C12 C17 H17B 108.1(10)
H17A C17 H17B 108.0(13)
C12 C17 H17C 109.6(10)
H17A C17 H17C 108.8(14)
H17B C17 H17C 111.1(15)
C16 C18 H18A 108.8(8)
C16 C18 H18B 110.9(8)
H18A C18 H18B 109.7(12)
C16 C18 H18C 108.8(11)
H18A C18 H18C 111.3(15)
H18B C18 H18C 107.3(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C10 1.3591(11)
O1 C1 1.4532(12)
O2 C10 1.2032(11)
N1 C10 1.3858(11)
N1 N2 1.4233(10)
N1 C2 1.4640(10)
N2 C11 1.2942(10)
C1 C2 1.5274(12)
C1 H1A 0.976(16)
C1 H1B 0.955(14)
C2 C3 1.5232(12)
C2 H2 0.930(15)
C3 C4 1.5112(12)
C3 H3A 0.943(17)
C3 H3B 0.984(12)
C4 C5 1.3947(13)
C4 C9 1.3966(13)
C5 C6 1.3938(15)
C5 H5 0.933(17)
C6 C7 1.3828(17)
C6 H6 0.97(2)
C7 C8 1.3880(17)
C7 H7 0.927(19)
C8 C9 1.3885(14)
C8 H8 1.007(19)
C9 H9 0.977(16)
C11 C16 1.4728(11)
C11 C12 1.5146(12)
C12 C13 1.5266(13)
C12 C17 1.5388(14)
C12 H12 0.939(14)
C13 C14 1.5266(14)
C13 H13A 0.983(14)
C13 H13B 1.035(14)
C14 C15 1.4922(14)
C14 H14A 0.948(17)
C14 H14B 0.994(17)
C15 C16 1.3438(12)
C15 H15 0.958(13)
C16 C18 1.5052(13)
C17 H17A 0.994(16)
C17 H17B 0.927(16)
C17 H17C 0.984(17)
C18 H18A 0.987(15)
C18 H18B 1.020(16)
C18 H18C 0.94(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139037918
