#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:45:29 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178962 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/91/4119172.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_4119172
loop_
_publ_author_name
'Gregory L. Adams'
'Patrick J. Carroll'
'Amos B. Smith'
_publ_section_title
;
 Access to the Akuammiline Family of Alkaloids: Total Synthesis of
 (+)-Scholarisine A
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              519
_journal_page_last               528
_journal_paper_doi               10.1021/ja3111626
_journal_volume                  135
_journal_year                    2013
_chemical_absolute_configuration syn
_chemical_formula_sum            'C18 H20 N2 O2'
_chemical_formula_weight         296.36
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.2327(6)
_cell_length_b                   12.5514(7)
_cell_length_c                   20.9905(11)
_cell_measurement_temperature    143(1)
_cell_volume                     2959.4(3)
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'phi and 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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0163
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            38096
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.475
_refine_diff_density_rms         0.181
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     409
_refine_ls_number_reflns         5206
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0286
_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)+(0.0532P)²+0.4813P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0790
_refine_ls_wR_factor_ref         0.0871
_reflns_number_gt                4993
_reflns_number_total             5206
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3111626_si_002.cif
_cod_data_source_block           CMPD(-)-50
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_database_code               4119172
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.76186(13) 0.55748(12) 0.63726(7) 0.0232(3) Uani 1 1 d . . .
C2 C 0.83746(14) 0.53342(13) 0.68806(8) 0.0286(3) Uani 1 1 d . . .
H2 H 0.8247 0.5619 0.7284 0.038 Uiso 1 1 calc R . .
C3 C 0.93193(15) 0.46590(14) 0.67624(8) 0.0333(4) Uani 1 1 d . . .
H3 H 0.9841 0.4493 0.7092 0.044 Uiso 1 1 calc R . .
C4 C 0.95090(15) 0.42194(14) 0.61595(8) 0.0338(4) Uani 1 1 d . . .
H4 H 1.0153 0.3766 0.6096 0.045 Uiso 1 1 calc R . .
C5 C 0.87593(15) 0.44447(13) 0.56569(8) 0.0284(3) Uani 1 1 d . . .
H5 H 0.8888 0.4143 0.5258 0.038 Uiso 1 1 calc R . .
C6 C 0.77947(13) 0.51406(12) 0.57584(7) 0.0229(3) Uani 1 1 d . . .
C7 C 0.68436(13) 0.55427(12) 0.53687(7) 0.0213(3) Uani 1 1 d . . .
C8 C 0.61506(13) 0.61657(11) 0.57530(7) 0.0212(3) Uani 1 1 d . . .
C9 C 0.50140(13) 0.66965(12) 0.55558(7) 0.0230(3) Uani 1 1 d . . .
H9 H 0.4446 0.6680 0.5910 0.031 Uiso 1 1 calc R . .
C10 C 0.45174(13) 0.60571(12) 0.49955(7) 0.0241(3) Uani 1 1 d . . .
H10A H 0.4300 0.5348 0.5137 0.032 Uiso 1 1 calc R . .
H10B H 0.3809 0.6403 0.4831 0.032 Uiso 1 1 calc R . .
C11 C 0.54592(13) 0.59832(12) 0.44720(7) 0.0223(3) Uani 1 1 d . . .
H11 H 0.5090 0.5635 0.4104 0.030 Uiso 1 1 calc R . .
C12 C 0.64936(13) 0.52775(12) 0.46919(7) 0.0224(3) Uani 1 1 d . . .
H12 H 0.6194 0.4544 0.4697 0.030 Uiso 1 1 calc R . .
C13 C 0.74709(15) 0.53151(12) 0.41993(7) 0.0271(3) Uani 1 1 d . . .
H13A H 0.8149 0.4915 0.4357 0.036 Uiso 1 1 calc R . .
H13B H 0.7192 0.4967 0.3815 0.036 Uiso 1 1 calc R . .
C14 C 0.70549(13) 0.71592(12) 0.39298(7) 0.0225(3) Uani 1 1 d . . .
C15 C 0.58500(13) 0.71162(12) 0.42580(7) 0.0209(3) Uani 1 1 d . . .
C16 C 0.60900(13) 0.78769(12) 0.48408(7) 0.0217(3) Uani 1 1 d . . .
H16A H 0.6874 0.7717 0.5010 0.029 Uiso 1 1 calc R . .
H16B H 0.6107 0.8605 0.4686 0.029 Uiso 1 1 calc R . .
C17 C 0.49088(15) 0.76276(13) 0.38208(7) 0.0276(3) Uani 1 1 d . . .
H17A H 0.4162 0.7669 0.4052 0.037 Uiso 1 1 calc R . .
H17B H 0.5155 0.8350 0.3724 0.037 Uiso 1 1 calc R . .
C18 C 0.46931(17) 0.70405(15) 0.31960(8) 0.0367(4) Uani 1 1 d . . .
H18A H 0.5437 0.6941 0.2979 0.055 Uiso 1 1 calc R . .
H18B H 0.4166 0.7452 0.2933 0.055 Uiso 1 1 calc R . .
H18C H 0.4340 0.6359 0.3283 0.055 Uiso 1 1 calc R . .
N1 N 0.66182(11) 0.62077(10) 0.63566(6) 0.0230(3) Uani 1 1 d . . .
H1 H 0.6335 0.6568 0.6671 0.031 Uiso 1 1 calc R . .
N2 N 0.52331(11) 0.78154(10) 0.53620(6) 0.0235(3) Uani 1 1 d . . .
O1 O 0.78608(10) 0.63885(9) 0.40389(5) 0.0283(3) Uani 1 1 d . . .
O2 O 0.73881(10) 0.79270(9) 0.36333(5) 0.0313(3) Uani 1 1 d . . .
C1' C 0.30584(14) 0.48113(12) 0.85583(7) 0.0252(3) Uani 1 1 d . . .
C2' C 0.24796(16) 0.52665(13) 0.90784(8) 0.0316(4) Uani 1 1 d . . .
H2' H 0.2629 0.5031 0.9491 0.042 Uiso 1 1 calc R . .
C3' C 0.16813(17) 0.60737(14) 0.89632(9) 0.0383(4) Uani 1 1 d . . .
H3' H 0.1288 0.6390 0.9304 0.051 Uiso 1 1 calc R . .
C4' C 0.14482(18) 0.64288(14) 0.83446(9) 0.0396(4) Uani 1 1 d . . .
H4' H 0.0897 0.6971 0.8282 0.053 Uiso 1 1 calc R . .
C5' C 0.20191(16) 0.59916(13) 0.78244(8) 0.0327(4) Uani 1 1 d . . .
H5' H 0.1862 0.6237 0.7415 0.043 Uiso 1 1 calc R . .
C6' C 0.28426(14) 0.51679(12) 0.79273(7) 0.0250(3) Uani 1 1 d . . .
C7' C 0.36330(14) 0.45660(12) 0.75257(7) 0.0228(3) Uani 1 1 d . . .
C8' C 0.42611(13) 0.39031(12) 0.79145(7) 0.0219(3) Uani 1 1 d . . .
C9' C 0.52243(13) 0.31691(12) 0.76939(7) 0.0238(3) Uani 1 1 d . . .
H9' H 0.5838 0.3111 0.8024 0.032 Uiso 1 1 calc R . .
C10' C 0.57592(13) 0.36798(13) 0.70944(7) 0.0247(3) Uani 1 1 d . . .
H10C H 0.6098 0.4368 0.7200 0.033 Uiso 1 1 calc R . .
H10D H 0.6389 0.3231 0.6927 0.033 Uiso 1 1 calc R . .
C11' C 0.47798(13) 0.38153(11) 0.65931(7) 0.0207(3) Uani 1 1 d . . .
H11' H 0.5152 0.4100 0.6206 0.028 Uiso 1 1 calc R . .
C12' C 0.38356(14) 0.46313(12) 0.68174(7) 0.0219(3) Uani 1 1 d . B .
H12' H 0.4160 0.5341 0.6730 0.029 Uiso 1 1 calc R . .
C14' C 0.31352(16) 0.28012(13) 0.60213(9) 0.0360(4) Uani 1 1 d . . .
C15' C 0.42480(13) 0.27100(11) 0.64264(7) 0.0208(3) Uani 1 1 d . B .
C16' C 0.38492(14) 0.21137(12) 0.70405(7) 0.0241(3) Uani 1 1 d . . .
H16C H 0.3129 0.2447 0.7199 0.032 Uiso 1 1 calc R B .
H16D H 0.3653 0.1385 0.6928 0.032 Uiso 1 1 calc R . .
C17' C 0.51527(14) 0.20098(12) 0.60634(7) 0.0250(3) Uani 1 1 d . . .
H17C H 0.5816 0.1857 0.6345 0.033 Uiso 1 1 calc R B .
H17D H 0.4774 0.1337 0.5960 0.033 Uiso 1 1 calc R . .
C18' C 0.5640(2) 0.24950(15) 0.54515(8) 0.0391(4) Uani 1 1 d . B .
H18D H 0.4992 0.2749 0.5195 0.059 Uiso 1 1 calc R . .
H18E H 0.6077 0.1964 0.5220 0.059 Uiso 1 1 calc R . .
H18F H 0.6159 0.3078 0.5554 0.059 Uiso 1 1 calc R . .
N1' N 0.39166(12) 0.40370(10) 0.85374(6) 0.0249(3) Uani 1 1 d . . .
H1' H 0.4193 0.3693 0.8859 0.033 Uiso 1 1 calc R . .
N2' N 0.47271(12) 0.20938(10) 0.75543(6) 0.0248(3) Uani 1 1 d . B .
O2' O 0.27813(13) 0.20954(11) 0.56862(8) 0.0567(4) Uani 1 1 d . B .
C13' C 0.27070(18) 0.45294(17) 0.64328(10) 0.0478(5) Uani 1 1 d . . .
H13C H 0.2067 0.4817 0.6691 0.064 Uiso 0.50 1 calc PR A 1
H13D H 0.2789 0.4996 0.6067 0.064 Uiso 0.50 1 calc PR A 1
H13X H 0.2073 0.4338 0.6725 0.064 Uiso 0.50 1 calc PR A 2
H13Y H 0.2518 0.5230 0.6266 0.064 Uiso 0.50 1 calc PR A 2
O1' O 0.2334(2) 0.3576(2) 0.62113(16) 0.0320(6) Uani 0.50 1 d P B 1
O1" O 0.2666(3) 0.3810(2) 0.59214(13) 0.0310(6) Uani 0.50 1 d P B 2
H2A H 0.4543 0.8181 0.5253 0.035 Uiso 1 1 d . C 2
H2A' H 0.5318 0.1580 0.7446 0.035 Uiso 1 1 d . D 2
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
N1 C1 C2 129.80(14)
N1 C1 C6 108.32(13)
C2 C1 C6 121.87(14)
C3 C2 C1 117.59(15)
C2 C3 C4 121.51(16)
C5 C4 C3 121.25(16)
C4 C5 C6 118.78(15)
C5 C6 C1 119.00(14)
C5 C6 C7 134.75(14)
C1 C6 C7 106.24(13)
C8 C7 C6 106.76(13)
C8 C7 C12 122.19(14)
C6 C7 C12 130.62(14)
C7 C8 N1 110.42(13)
C7 C8 C9 125.21(13)
N1 C8 C9 124.33(13)
N2 C9 C8 110.82(12)
N2 C9 C10 110.28(12)
C8 C9 C10 106.85(12)
C11 C10 C9 109.41(12)
C10 C11 C12 110.09(12)
C10 C11 C15 110.35(12)
C12 C11 C15 113.68(12)
C13 C12 C7 116.62(13)
C13 C12 C11 109.11(12)
C7 C12 C11 110.67(12)
O1 C13 C12 113.97(12)
O2 C14 O1 116.97(14)
O2 C14 C15 122.58(14)
O1 C14 C15 119.80(12)
C14 C15 C17 109.05(12)
C14 C15 C11 114.52(12)
C17 C15 C11 111.07(12)
C14 C15 C16 100.26(11)
C17 C15 C16 109.13(12)
C11 C15 C16 112.24(11)
N2 C16 C15 115.93(12)
C18 C17 C15 114.87(13)
C8 N1 C1 108.23(12)
C16 N2 C9 111.42(12)
C14 O1 C13 120.17(12)
N1' C1' C2' 130.13(15)
N1' C1' C6' 108.31(13)
C2' C1' C6' 121.50(15)
C3' C2' C1' 117.96(16)
C2' C3' C4' 121.38(16)
C5' C4' C3' 121.42(17)
C4' C5' C6' 118.51(16)
C5' C6' C1' 119.23(14)
C5' C6' C7' 134.69(15)
C1' C6' C7' 106.01(14)
C8' C7' C6' 106.83(13)
C8' C7' C12' 123.10(14)
C6' C7' C12' 130.01(14)
C7' C8' N1' 110.45(13)
C7' C8' C9' 124.46(13)
N1' C8' C9' 125.04(13)
N2' C9' C8' 110.37(12)
N2' C9' C10' 111.33(12)
C8' C9' C10' 106.25(12)
C11' C10' C9' 109.18(12)
C10' C11' C12' 110.89(12)
C10' C11' C15' 109.41(12)
C12' C11' C15' 113.38(12)
C7' C12' C13' 113.37(15)
C7' C12' C11' 111.58(12)
C13' C12' C11' 110.91(13)
O2' C14' O1' 118.19(18)
O2' C14' O1" 117.39(18)
O1' C14' O1" 32.37(13)
O2' C14' C15' 123.13(15)
O1' C14' C15' 115.33(17)
O1" C14' C15' 117.81(17)
C14' C15' C17' 107.98(12)
C14' C15' C11' 112.12(12)
C17' C15' C11' 111.53(12)
C14' C15' C16' 105.28(13)
C17' C15' C16' 108.93(12)
C11' C15' C16' 110.75(12)
N2' C16' C15' 115.16(12)
C18' C17' C15' 115.15(13)
C1' N1' C8' 108.40(12)
C16' N2' C9' 112.50(11)
O1' C13' O1" 32.51(13)
O1' C13' C12' 121.35(19)
O1" C13' C12' 119.43(18)
C13' O1' C14' 121.3(2)
C14' O1" C13' 117.3(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.377(2)
C1 C2 1.396(2)
C1 C6 1.414(2)
C2 C3 1.380(3)
C3 C4 1.397(3)
C4 C5 1.379(2)
C5 C6 1.408(2)
C6 C7 1.437(2)
C7 C8 1.367(2)
C7 C12 1.511(2)
C8 N1 1.3725(19)
C8 C9 1.498(2)
C9 N2 1.483(2)
C9 C10 1.529(2)
C10 C11 1.528(2)
C11 C12 1.532(2)
C11 C15 1.555(2)
C12 C13 1.509(2)
C13 O1 1.4561(19)
C14 O2 1.2067(19)
C14 O1 1.344(2)
C14 C15 1.520(2)
C15 C17 1.540(2)
C15 C16 1.5749(19)
C16 N2 1.4593(19)
C17 C18 1.524(2)
C1' N1' 1.370(2)
C1' C2' 1.393(2)
C1' C6' 1.419(2)
C2' C3' 1.374(3)
C3' C4' 1.398(3)
C4' C5' 1.380(2)
C5' C6' 1.404(2)
C6' C7' 1.438(2)
C7' C8' 1.362(2)
C7' C12' 1.506(2)
C8' N1' 1.3739(19)
C8' C9' 1.495(2)
C9' N2' 1.490(2)
C9' C10' 1.535(2)
C10' C11' 1.532(2)
C11' C12' 1.548(2)
C11' C15' 1.551(2)
C12' C13' 1.508(2)
C14' O2' 1.199(2)
C14' O1' 1.384(3)
C14' O1" 1.388(3)
C14' C15' 1.516(2)
C15' C17' 1.545(2)
C15' C16' 1.556(2)
C16' N2' 1.462(2)
C17' C18' 1.523(2)
C13' O1' 1.351(3)
C13' O1" 1.403(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
N1 H1 N2' 0.86 2.12 2.9576(18) 163.5 3_656
N1' H1' N2 0.86 2.07 2.9327(18) 176.7 3_646
N2 H2A O1 0.93 2.46 3.1114(17) 126.8 2_466
