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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/1/50/44/1504485.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_1504485
loop_
_publ_author_name
'Dunet, Guillaume'
'Mayer, Peter'
'Knochel, Paul'
_publ_section_title
;
 Highly diastereoselective addition of cinnamylzinc derivatives to
 alpha-chiral carbonyl compounds.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              117
_journal_page_last               120
_journal_paper_doi               10.1021/ol702607t
_journal_volume                  10
_journal_year                    2008
_chemical_formula_moiety         'C18 H23 N O'
_chemical_formula_sum            'C18 H23 N O'
_chemical_formula_weight         269.381
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_code                C18H23NO_ln055_knochel
_audit_creation_date             29-Jan-07
_audit_creation_method           'form98_non/compatible with shelxl97-2'
_audit_update_record             16-Oct-07
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.8059(4)
_cell_length_b                   8.5365(3)
_cell_length_c                   14.3248(6)
_cell_measurement_reflns_used    7383
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      3.134
_cell_volume                     1565.95(10)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement
'SHELXL-97 (G. M. Sheldrick. University of Göttingen, 97-2 version)'
_computing_structure_solution
;
A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A.
Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for
crystal structure determination and refinement; J. Appl. Crystallogr. 1999,
32, 115-119.
;
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       phi/omega-scan
_diffrn_orient_matrix_type       'by Bruker AXS Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.0789349
_diffrn_orient_matrix_UB_12      0.0527339
_diffrn_orient_matrix_UB_13      -0.0209332
_diffrn_orient_matrix_UB_21      -0.0014671
_diffrn_orient_matrix_UB_22      -0.0308713
_diffrn_orient_matrix_UB_23      -0.0641162
_diffrn_orient_matrix_UB_31      -0.0865439
_diffrn_orient_matrix_UB_32      0.0486209
_diffrn_orient_matrix_UB_33      -0.0180058
_diffrn_radiation_collimation    0.20
_diffrn_radiation_monochromator  'MONTEL, graded multilayered X-ray optics'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2598
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.18
_diffrn_source_current           55.00
_diffrn_source_power             3.025
_diffrn_source_type              'FR 591 generator'
_diffrn_source_voltage           55.00
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.14263(7)
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.8(16)
_refine_ls_extinction_coef       0.031(3)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         2598
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0329P)²+0.2943P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0839
_reflns_number_gt                2285
_reflns_number_total             2598
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol702607t-file002.cif
_cod_data_source_block           ln055
_cod_database_code               1504485
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, 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
O O 0.03981(9) 0.31633(16) 0.66318(11) 0.0436(3) Uani 1 1 d
N N 0.03926(16) 0.4062(3) 1.06550(14) 0.0619(6) Uani 1 1 d
C1 C 0.15142(13) 0.2977(2) 0.66634(14) 0.0352(4) Uani 1 1 d
C2 C 0.17902(16) 0.2366(2) 0.76537(14) 0.0381(5) Uani 1 1 d
C3 C 0.29882(17) 0.2349(2) 0.77931(15) 0.0433(5) Uani 1 1 d
C4 C 0.34945(17) 0.3928(3) 0.76132(17) 0.0476(5) Uani 1 1 d
C5 C 0.32226(16) 0.4527(2) 0.66428(16) 0.0443(5) Uani 1 1 d
C6 C 0.20424(15) 0.4551(2) 0.64892(15) 0.0405(5) Uani 1 1 d
C7 C 0.12359(19) 0.3300(3) 0.84252(15) 0.0446(5) Uani 1 1 d
C8 C 0.1120(3) 0.2334(3) 0.93084(17) 0.0642(7) Uani 1 1 d
C9 C 0.07035(19) 0.3284(3) 1.00723(15) 0.0536(6) Uani 1 1 d
C10 C 0.18079(15) 0.1721(2) 0.59137(13) 0.0359(4) Uani 1 1 d
C11 C 0.16186(16) 0.2276(2) 0.49224(14) 0.0394(5) Uani 1 1 d
C12 C 0.24530(18) 0.2647(2) 0.43489(15) 0.0473(5) Uani 1 1 d
C13 C 0.2295(2) 0.3144(3) 0.34339(17) 0.0588(6) Uani 1 1 d
C14 C 0.1294(3) 0.3255(3) 0.30814(17) 0.0608(7) Uani 1 1 d
C15 C 0.0459(2) 0.2869(3) 0.36378(17) 0.0596(7) Uani 1 1 d
C16 C 0.06144(19) 0.2386(3) 0.45518(17) 0.0519(6) Uani 1 1 d
C17 C 0.12303(17) 0.0196(2) 0.60816(15) 0.0414(5) Uani 1 1 d
C18 C 0.1664(2) -0.1184(2) 0.61125(17) 0.0549(6) Uani 1 1 d
H2 H 0.1525(14) 0.127(2) 0.7682(14) 0.032(5) Uiso 1 1 d
H10 H 0.2563(15) 0.147(2) 0.5980(13) 0.032(5) Uiso 1 1 d
H61 H 0.1803(15) 0.492(2) 0.5875(16) 0.039(5) Uiso 1 1 d
H31 H 0.3083(17) 0.198(3) 0.8427(17) 0.048(6) Uiso 1 1 d
H12 H 0.3180(18) 0.256(3) 0.4597(17) 0.049(6) Uiso 1 1 d
H62 H 0.1712(16) 0.530(3) 0.6964(18) 0.050(6) Uiso 1 1 d
H17 H 0.0456(18) 0.035(3) 0.6164(17) 0.060(7) Uiso 1 1 d
H51 H 0.3543(16) 0.387(2) 0.6202(16) 0.038(5) Uiso 1 1 d
H52 H 0.3511(15) 0.567(3) 0.6520(16) 0.054(6) Uiso 1 1 d
H181 H 0.250(2) -0.130(3) 0.606(2) 0.082(9) Uiso 1 1 d
H41 H 0.3292(19) 0.472(3) 0.8070(19) 0.064(7) Uiso 1 1 d
H81 H 0.178(3) 0.181(4) 0.955(2) 0.093(10) Uiso 1 1 d
H71 H 0.1627(18) 0.420(3) 0.8580(18) 0.059(7) Uiso 1 1 d
H16 H -0.003(2) 0.211(3) 0.495(2) 0.081(8) Uiso 1 1 d
H32 H 0.3302(15) 0.156(2) 0.7378(14) 0.036(5) Uiso 1 1 d
H182 H 0.125(2) -0.210(3) 0.6225(19) 0.064(7) Uiso 1 1 d
H42 H 0.4282(19) 0.379(3) 0.7682(17) 0.052(6) Uiso 1 1 d
H1 H 0.0297(19) 0.409(3) 0.6347(18) 0.066(8) Uiso 1 1 d
H15 H -0.028(2) 0.290(3) 0.341(2) 0.076(8) Uiso 1 1 d
H72 H 0.046(2) 0.356(3) 0.8191(18) 0.066(7) Uiso 1 1 d
H13 H 0.294(2) 0.342(3) 0.303(2) 0.075(8) Uiso 1 1 d
H14 H 0.117(2) 0.362(3) 0.244(2) 0.082(9) Uiso 1 1 d
H82 H 0.059(3) 0.138(4) 0.915(2) 0.105(11) 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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.080000
-1 0 0 0.080000
0 -1 0 0.050000
0 1 0 0.140000
0 0 1 0.110000
0 0 -1 0.150000
0 2 -3 0.140000
0 -2 3 0.080000
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O H1 104.7(16)
O C1 C6 109.78(14)
O C1 C2 106.98(15)
C6 C1 C2 110.17(16)
O C1 C10 107.04(15)
C6 C1 C10 112.67(15)
C2 C1 C10 110.01(14)
C7 C2 C3 111.72(18)
C7 C2 C1 112.19(15)
C3 C2 C1 110.30(15)
C7 C2 H2 107.5(11)
C3 C2 H2 108.9(10)
C1 C2 H2 106.0(12)
C4 C3 C2 113.15(16)
C4 C3 H31 113.3(13)
C2 C3 H31 104.3(13)
C4 C3 H32 109.5(11)
C2 C3 H32 109.4(11)
H31 C3 H32 106.9(18)
C3 C4 C5 110.84(18)
C3 C4 H41 112.9(15)
C5 C4 H41 108.5(15)
C3 C4 H42 107.9(13)
C5 C4 H42 110.6(14)
H41 C4 H42 106(2)
C4 C5 C6 111.26(17)
C4 C5 H51 108.3(12)
C6 C5 H51 110.1(12)
C4 C5 H52 112.4(12)
C6 C5 H52 107.9(11)
H51 C5 H52 106.7(17)
C1 C6 C5 113.80(16)
C1 C6 H61 106.9(11)
C5 C6 H61 116.2(12)
C1 C6 H62 105.1(12)
C5 C6 H62 108.7(12)
H61 C6 H62 105.3(17)
C8 C7 C2 111.29(17)
C8 C7 H71 107.3(16)
C2 C7 H71 110.2(15)
C8 C7 H72 106.5(14)
C2 C7 H72 108.0(14)
H71 C7 H72 114(2)
C9 C8 C7 111.0(2)
C9 C8 H81 107.0(18)
C7 C8 H81 116.1(18)
C9 C8 H82 110.3(19)
C7 C8 H82 107.4(19)
H81 C8 H82 105(3)
N C9 C8 177.9(3)
C17 C10 C11 109.81(16)
C17 C10 C1 111.26(16)
C11 C10 C1 112.96(15)
C17 C10 H10 106.0(11)
C11 C10 H10 108.2(11)
C1 C10 H10 108.3(11)
C12 C11 C16 118.1(2)
C12 C11 C10 120.25(19)
C16 C11 C10 121.65(19)
C11 C12 C13 121.1(2)
C11 C12 H12 119.4(13)
C13 C12 H12 119.6(14)
C14 C13 C12 120.0(2)
C14 C13 H13 121.1(15)
C12 C13 H13 118.9(15)
C15 C14 C13 119.6(2)
C15 C14 H14 119.3(17)
C13 C14 H14 121.1(17)
C14 C15 C16 120.5(3)
C14 C15 H15 122.4(17)
C16 C15 H15 117.1(17)
C15 C16 C11 120.8(2)
C15 C16 H16 118.1(17)
C11 C16 H16 121.1(17)
C18 C17 C10 125.0(2)
C18 C17 H17 122.1(14)
C10 C17 H17 112.9(13)
C17 C18 H181 120.1(15)
C17 C18 H182 120.6(15)
H181 C18 H182 119(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O C1 1.439(2)
O H1 0.90(3)
N C9 1.139(3)
C1 C6 1.525(3)
C1 C2 1.552(3)
C1 C10 1.564(3)
C2 C7 1.537(3)
C2 C3 1.547(3)
C2 H2 1.00(2)
C3 C4 1.518(3)
C3 H31 0.97(2)
C3 H32 0.99(2)
C4 C5 1.522(3)
C4 H41 0.98(3)
C4 H42 1.02(2)
C5 C6 1.527(3)
C5 H51 0.94(2)
C5 H52 1.06(2)
C6 H61 0.98(2)
C6 H62 1.03(2)
C7 C8 1.517(3)
C7 H71 0.94(3)
C7 H72 1.07(3)
C8 C9 1.463(3)
C8 H81 1.02(3)
C8 H82 1.08(4)
C10 C17 1.516(3)
C10 C11 1.517(3)
C10 H10 0.994(19)
C11 C12 1.384(3)
C11 C16 1.394(3)
C12 C13 1.393(3)
C12 H12 1.00(2)
C13 C14 1.381(4)
C13 H13 1.04(3)
C14 C15 1.374(4)
C14 H14 0.99(3)
C15 C16 1.387(3)
C15 H15 1.01(3)
C16 H16 1.03(3)
C17 C18 1.304(3)
C17 H17 1.01(2)
C18 H181 1.07(3)
C18 H182 0.96(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O H1 N 0.90(3) 2.06(3) 2.931(2) 162(2) 2_564
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O C1 C2 C7 -47.0(2)
C6 C1 C2 C7 72.3(2)
C10 C1 C2 C7 -162.94(17)
O C1 C2 C3 -172.26(15)
C6 C1 C2 C3 -52.99(19)
C10 C1 C2 C3 71.81(19)
C7 C2 C3 C4 -70.4(2)
C1 C2 C3 C4 55.1(2)
C2 C3 C4 C5 -55.4(2)
C3 C4 C5 C6 53.7(2)
O C1 C6 C5 171.91(17)
C2 C1 C6 C5 54.3(2)
C10 C1 C6 C5 -68.9(2)
C4 C5 C6 C1 -54.9(2)
C3 C2 C7 C8 -80.0(3)
C1 C2 C7 C8 155.5(2)
C2 C7 C8 C9 173.4(2)
C7 C8 C9 N -29(8)
O C1 C10 C17 -56.5(2)
C6 C1 C10 C17 -177.31(16)
C2 C1 C10 C17 59.34(19)
O C1 C10 C11 67.49(19)
C6 C1 C10 C11 -53.3(2)
C2 C1 C10 C11 -176.62(17)
C17 C10 C11 C12 -127.62(19)
C1 C10 C11 C12 107.6(2)
C17 C10 C11 C16 50.4(2)
C1 C10 C11 C16 -74.4(2)
C16 C11 C12 C13 1.2(3)
C10 C11 C12 C13 179.4(2)
C11 C12 C13 C14 -0.8(3)
C12 C13 C14 C15 -0.2(4)
C13 C14 C15 C16 0.7(4)
C14 C15 C16 C11 -0.2(4)
C12 C11 C16 C15 -0.7(3)
C10 C11 C16 C15 -178.8(2)
C11 C10 C17 C18 104.1(2)
C1 C10 C17 C18 -130.1(2)
loop_
_reflns_scale_group_code
_reflns_scale_meas_F
1 1.0
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 101457790
