#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/40/4024074.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_4024074
loop_
_publ_author_name
'Harry W. Gibson'
'Michael A. G. Berg'
'Jennifer Clifton Dickson'
'Pierre R. Lecavalier'
'Hong Wang'
'Joseph S. Merola'
_publ_contact_author             'Berg, Michael A. G.'
_publ_contact_author_email       bergm@vt.edu
_publ_section_title
;
 Diastereomeric Reissert Compounds of Isoquinoline and
 6,7-Dimethoxy-3,4-dihydroisoquinoline in Stereoselective Synthesis
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5759
_journal_page_last               5770
_journal_paper_doi               10.1021/jo070786k
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration rm
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C23 H32 N2 O4'
_chemical_formula_sum            'C23 H32 N2 O4'
_chemical_formula_weight         400.51
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2006-10-03T16:55:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90(0)
_cell_angle_beta                 95.02(3)
_cell_angle_gamma                90(0)
_cell_formula_units_Z            2
_cell_length_a                   8.633(3)
_cell_length_b                   9.999(3)
_cell_length_c                   13.048(5)
_cell_measurement_reflns_used    2906
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.75
_cell_measurement_wavelength     0.71073
_cell_volume                     1122.0(7)
_computing_cell_refinement
'Siemens SHELXTL PLUS (VMS) (Sheldrick, 1990)'
_computing_data_collection
'Siemens SHELXTL PLUS (VMS) (Sheldrick, 1990)'
_computing_data_reduction
'Siemens SHELXTL PLUS (VMS) (Sheldrick, 1990)'
_computing_molecular_graphics    'Ortep 3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'Siemens SHELXTL PLUS (VMS) (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'scintillation counter'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four circle'
_diffrn_measurement_device_type  'Siemens R3m/V four-circle defractometer'
_diffrn_measurement_method       'Wyckoff scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2900
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         2.37
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 300
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.080(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         2728
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0543P)²+0.1071P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1016
_reflns_number_gt                2429
_reflns_number_total             2728
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070786krom20070415_124510.cif
_cod_data_source_block           dihydro
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4024074
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3770(2) 0.3024(2) 0.72024(14) 0.0358(4) Uani 1 1 d . . .
H1 H 0.3602 0.3837 0.6788 0.043 Uiso 1 1 calc R . .
C2 C 0.2229(3) 0.2376(2) 0.72711(17) 0.0480(5) Uani 1 1 d . . .
C3 C 0.5506(3) 0.2468(3) 0.87758(15) 0.0488(5) Uani 1 1 d . . .
H3A H 0.4946 0.1654 0.8907 0.059 Uiso 1 1 calc R . .
H3B H 0.5894 0.2849 0.9433 0.059 Uiso 1 1 calc R . .
C4 C 0.6856(3) 0.2149(3) 0.81477(17) 0.0561(6) Uani 1 1 d . . .
H4A H 0.7518 0.2929 0.812 0.067 Uiso 1 1 calc R . .
H4B H 0.7471 0.1431 0.8476 0.067 Uiso 1 1 calc R . .
C5 C 0.7205(2) 0.0939(3) 0.64786(18) 0.0497(5) Uani 1 1 d . . .
H5 H 0.8195 0.0692 0.6751 0.06 Uiso 1 1 calc R . .
C6 C 0.6679(2) 0.0516(3) 0.55073(17) 0.0471(5) Uani 1 1 d . . .
C7 C 0.5175(2) 0.0863(2) 0.50966(16) 0.0435(5) Uani 1 1 d . . .
C8 C 0.4277(2) 0.1669(2) 0.56571(15) 0.0408(4) Uani 1 1 d . . .
H8 H 0.3296 0.193 0.5378 0.049 Uiso 1 1 calc R . .
C9 C 0.4820(2) 0.2103(2) 0.66469(14) 0.0371(4) Uani 1 1 d . . .
C10 C 0.6278(2) 0.1735(2) 0.70686(15) 0.0425(5) Uani 1 1 d . . .
C11 C 0.3821(2) 0.4437(2) 0.87402(15) 0.0402(4) Uani 1 1 d . . .
C12 C 0.1932(3) 0.6192(2) 0.85706(16) 0.0455(5) Uani 1 1 d . . .
H12 H 0.2615 0.657 0.9137 0.055 Uiso 1 1 calc R . .
C13 C 0.1668(3) 0.7222(2) 0.77161(16) 0.0447(5) Uani 1 1 d . . .
H13 H 0.0984 0.681 0.7165 0.054 Uiso 1 1 calc R . .
C14 C 0.0776(3) 0.8399(3) 0.8134(2) 0.0570(6) Uani 1 1 d . . .
H14A H 0.1415 0.882 0.8692 0.068 Uiso 1 1 calc R . .
H14B H 0.0567 0.9057 0.7593 0.068 Uiso 1 1 calc R . .
C15 C -0.0753(3) 0.7953(3) 0.85231(19) 0.0596(6) Uani 1 1 d . . .
H15A H -0.1273 0.8722 0.8789 0.072 Uiso 1 1 calc R . .
H15B H -0.1421 0.7591 0.7953 0.072 Uiso 1 1 calc R . .
C16 C -0.0514(3) 0.6906(3) 0.93592(19) 0.0640(7) Uani 1 1 d . . .
H16 H 0.0093 0.7309 0.995 0.077 Uiso 1 1 calc R . .
C17 C 0.0422(3) 0.5733(3) 0.8972(2) 0.0591(6) Uani 1 1 d . . .
H17A H 0.0654 0.5104 0.953 0.071 Uiso 1 1 calc R . .
H17B H -0.0202 0.5272 0.8427 0.071 Uiso 1 1 calc R . .
C18 C 0.3180(3) 0.7627(3) 0.7245(2) 0.0598(6) Uani 1 1 d . . .
H18 H 0.3709 0.6797 0.7081 0.072 Uiso 1 1 calc R . .
C19 C 0.4316(4) 0.8421(5) 0.7984(3) 0.1028(13) Uani 1 1 d . . .
H19A H 0.5288 0.8522 0.7686 0.154 Uiso 1 1 calc R . .
H19B H 0.4484 0.7951 0.8625 0.154 Uiso 1 1 calc R . .
H19C H 0.3887 0.9288 0.8102 0.154 Uiso 1 1 calc R . .
C20 C 0.2826(4) 0.8374(4) 0.6238(3) 0.0834(9) Uani 1 1 d . . .
H20A H 0.2411 0.924 0.6375 0.125 Uiso 1 1 calc R . .
H20B H 0.2078 0.7878 0.5802 0.125 Uiso 1 1 calc R . .
H20C H 0.3764 0.8474 0.5901 0.125 Uiso 1 1 calc R . .
C21 C -0.2063(4) 0.6423(5) 0.9716(3) 0.1070(15) Uani 1 1 d . . .
H21A H -0.2642 0.7175 0.9934 0.161 Uiso 1 1 calc R . .
H21B H -0.1866 0.5811 1.0279 0.161 Uiso 1 1 calc R . .
H21C H -0.2651 0.5978 0.9157 0.161 Uiso 1 1 calc R . .
C22 C 0.9065(3) -0.0526(5) 0.5205(3) 0.0949(13) Uani 1 1 d . . .
H22A H 0.9621 0.0299 0.5326 0.142 Uiso 1 1 calc R . .
H22B H 0.953 -0.103 0.4686 0.142 Uiso 1 1 calc R . .
H22C H 0.9109 -0.1034 0.5831 0.142 Uiso 1 1 calc R . .
C23 C 0.3224(3) 0.0640(5) 0.3706(2) 0.0907(12) Uani 1 1 d . . .
H23A H 0.2477 0.0324 0.4153 0.136 Uiso 1 1 calc R . .
H23B H 0.3054 0.0203 0.3051 0.136 Uiso 1 1 calc R . .
H23C H 0.311 0.1589 0.3615 0.136 Uiso 1 1 calc R . .
N1 N 0.1048(3) 0.1892(3) 0.7307(2) 0.0812(8) Uani 1 1 d . . .
N2 N 0.4459(2) 0.34189(18) 0.82149(12) 0.0399(4) Uani 1 1 d . . .
O1 O 0.26853(17) 0.50444(15) 0.81435(11) 0.0455(4) Uani 1 1 d . . .
O2 O 0.4232(2) 0.47401(19) 0.96198(12) 0.0611(5) Uani 1 1 d . . .
O3 O 0.75109(18) -0.0249(2) 0.48727(13) 0.0649(5) Uani 1 1 d . . .
O4 O 0.47370(19) 0.0352(2) 0.41450(11) 0.0573(4) 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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 C1 C2 111.08(16) . . ?
N2 C1 C9 112.54(15) . . ?
C2 C1 C9 109.76(17) . . ?
N1 C2 C1 178.7(3) . . ?
N2 C3 C4 109.68(18) . . ?
C10 C4 C3 110.77(18) . . ?
C6 C5 C10 121.41(19) . . ?
C5 C6 O3 125.3(2) . . ?
C5 C6 C7 119.71(19) . . ?
O3 C6 C7 114.97(19) . . ?
O4 C7 C8 125.47(19) . . ?
O4 C7 C6 115.32(19) . . ?
C8 C7 C6 119.21(19) . . ?
C7 C8 C9 120.88(18) . . ?
C10 C9 C8 120.30(18) . . ?
C10 C9 C1 122.22(16) . . ?
C8 C9 C1 117.44(16) . . ?
C9 C10 C5 118.43(18) . . ?
C9 C10 C4 121.01(18) . . ?
C5 C10 C4 120.54(18) . . ?
O2 C11 O1 125.10(19) . . ?
O2 C11 N2 124.32(19) . . ?
O1 C11 N2 110.57(16) . . ?
O1 C12 C17 108.63(19) . . ?
O1 C12 C13 107.28(16) . . ?
C17 C12 C13 112.37(18) . . ?
C12 C13 C14 107.88(18) . . ?
C12 C13 C18 113.07(19) . . ?
C14 C13 C18 114.1(2) . . ?
C15 C14 C13 111.8(2) . . ?
C16 C15 C14 112.1(2) . . ?
C15 C16 C21 111.7(3) . . ?
C15 C16 C17 109.53(19) . . ?
C21 C16 C17 110.9(3) . . ?
C12 C17 C16 112.0(2) . . ?
C20 C18 C19 111.0(3) . . ?
C20 C18 C13 111.1(2) . . ?
C19 C18 C13 113.7(2) . . ?
C11 N2 C1 120.36(16) . . ?
C11 N2 C3 119.36(16) . . ?
C1 N2 C3 117.64(17) . . ?
C11 O1 C12 117.61(15) . . ?
C6 O3 C22 117.4(2) . . ?
C7 O4 C23 117.78(19) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.455(2) . ?
C1 C2 1.490(3) . ?
C1 C9 1.520(3) . ?
C2 N1 1.133(3) . ?
C3 N2 1.463(3) . ?
C3 C4 1.516(3) . ?
C4 C10 1.510(3) . ?
C5 C6 1.375(3) . ?
C5 C10 1.405(3) . ?
C6 O3 1.375(3) . ?
C6 C7 1.404(3) . ?
C7 O4 1.365(3) . ?
C7 C8 1.372(3) . ?
C8 C9 1.404(3) . ?
C9 C10 1.378(3) . ?
C11 O2 1.210(2) . ?
C11 O1 1.343(2) . ?
C11 N2 1.369(3) . ?
C12 O1 1.454(2) . ?
C12 C17 1.518(3) . ?
C12 C13 1.521(3) . ?
C13 C14 1.532(3) . ?
C13 C18 1.545(3) . ?
C14 C15 1.523(4) . ?
C15 C16 1.513(4) . ?
C16 C21 1.532(4) . ?
C16 C17 1.534(4) . ?
C18 C20 1.519(4) . ?
C18 C19 1.535(5) . ?
C22 O3 1.401(3) . ?
C23 O4 1.409(3) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C3 C4 C10 -51.5(3) . . . . ?
C10 C5 C6 O3 179.2(2) . . . . ?
C10 C5 C6 C7 -1.1(4) . . . . ?
C5 C6 C7 O4 -177.5(2) . . . . ?
O3 C6 C7 O4 2.3(3) . . . . ?
C5 C6 C7 C8 2.7(4) . . . . ?
O3 C6 C7 C8 -177.5(2) . . . . ?
O4 C7 C8 C9 177.7(2) . . . . ?
C6 C7 C8 C9 -2.5(3) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
C7 C8 C9 C1 178.3(2) . . . . ?
N2 C1 C9 C10 -1.8(3) . . . . ?
C2 C1 C9 C10 -126.0(2) . . . . ?
N2 C1 C9 C8 -179.42(18) . . . . ?
C2 C1 C9 C8 56.3(2) . . . . ?
C8 C9 C10 C5 1.0(3) . . . . ?
C1 C9 C10 C5 -176.6(2) . . . . ?
C8 C9 C10 C4 -177.6(2) . . . . ?
C1 C9 C10 C4 4.8(3) . . . . ?
C6 C5 C10 C9 -0.7(4) . . . . ?
C6 C5 C10 C4 177.9(2) . . . . ?
C3 C4 C10 C9 22.4(3) . . . . ?
C3 C4 C10 C5 -156.2(2) . . . . ?
O1 C12 C13 C14 176.24(17) . . . . ?
C17 C12 C13 C14 56.9(2) . . . . ?
O1 C12 C13 C18 -56.6(2) . . . . ?
C17 C12 C13 C18 -175.9(2) . . . . ?
C12 C13 C14 C15 -57.2(3) . . . . ?
C18 C13 C14 C15 176.2(2) . . . . ?
C13 C14 C15 C16 58.1(3) . . . . ?
C14 C15 C16 C21 -177.7(3) . . . . ?
C14 C15 C16 C17 -54.4(3) . . . . ?
O1 C12 C17 C16 -175.40(19) . . . . ?
C13 C12 C17 C16 -56.9(3) . . . . ?
C15 C16 C17 C12 53.7(3) . . . . ?
C21 C16 C17 C12 177.5(3) . . . . ?
C12 C13 C18 C20 165.9(2) . . . . ?
C14 C13 C18 C20 -70.3(3) . . . . ?
C12 C13 C18 C19 -68.1(3) . . . . ?
C14 C13 C18 C19 55.7(3) . . . . ?
O2 C11 N2 C1 172.7(2) . . . . ?
O1 C11 N2 C1 -7.4(3) . . . . ?
O2 C11 N2 C3 11.6(3) . . . . ?
O1 C11 N2 C3 -168.51(19) . . . . ?
C2 C1 N2 C11 -69.0(2) . . . . ?
C9 C1 N2 C11 167.50(17) . . . . ?
C2 C1 N2 C3 92.5(2) . . . . ?
C9 C1 N2 C3 -31.0(3) . . . . ?
C4 C3 N2 C11 -139.5(2) . . . . ?
C4 C3 N2 C1 58.9(3) . . . . ?
O2 C11 O1 C12 2.7(3) . . . . ?
N2 C11 O1 C12 -177.21(18) . . . . ?
C17 C12 O1 C11 -98.2(2) . . . . ?
C13 C12 O1 C11 140.10(18) . . . . ?
C5 C6 O3 C22 -5.8(4) . . . . ?
C7 C6 O3 C22 174.5(3) . . . . ?
C8 C7 O4 C23 -1.8(4) . . . . ?
C6 C7 O4 C23 178.4(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658830
