#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/23/1502391.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_1502391
loop_
_publ_author_name
'Goldberg, Alexander F. G.'
'Stoltz, Brian M.'
_publ_section_title
;
 A palladium-catalyzed vinylcyclopropane (3+2) cycloaddition approach to
 the Melodinus alkaloids.
;
_journal_issue                   16
_journal_name_full               'Organic letters'
_journal_page_first              4474
_journal_page_last               4476
_journal_paper_doi               10.1021/ol2017615
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C16 H18 N2 O3'
_chemical_formula_sum            'C16 H18 N2 O3'
_chemical_formula_weight         286.32
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                71.309(2)
_cell_angle_beta                 69.829(2)
_cell_angle_gamma                75.7590(10)
_cell_formula_units_Z            2
_cell_length_a                   7.6777(3)
_cell_length_b                   9.1864(3)
_cell_length_c                   10.8584(4)
_cell_measurement_reflns_used    8222
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      36.32
_cell_measurement_theta_min      2.71
_cell_volume                     673.01(4)
_computing_cell_refinement       'Bruker SAINT-Plus v7.66A'
_computing_data_collection       'Bruker SMART v5.630'
_computing_data_reduction        'Bruker SAINT-Plus v7.66A'
_computing_molecular_graphics    'Bruker XP v5.1'
_computing_publication_material  'Bruker XCIF 2008'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       'ω scans at 10 φ settings'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24459
_diffrn_reflns_theta_full        36.35
_diffrn_reflns_theta_max         36.35
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9815
_exptl_absorpt_correction_T_min  0.9654
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Column
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.666
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.646
_refine_ls_hydrogen_treatment    Unrestrained
_refine_ls_matrix_type           'Full matrix'
_refine_ls_number_parameters     262
_refine_ls_number_reflns         6449
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.646
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0623
_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/s²(Fo²)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0954
_reflns_number_gt                4636
_reflns_number_total             6449
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2017615_si_003.cif
_cod_data_source_block           afg03
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_weighting_scheme' value 'Sigma' changed to
'sigma' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Direct methods' was changed to
'direct'.

'_atom_sites_solution_secondary' value 'Difference Fourier map' was
changed to 'difmap'.

'_atom_sites_solution_hydrogens' value 'Difference Fourier map' was
changed to 'difmap'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1502391
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.44078(10) 0.70889(9) 0.41778(8) 0.01902(17) Uani 1 1 d
O2 O 0.70244(12) 0.95767(9) 0.02369(8) 0.0255(2) Uani 1 1 d
O3 O 0.66146(11) 0.70729(9) 0.11173(8) 0.01872(17) Uani 1 1 d
N1 N 0.72761(12) 0.56257(11) 0.39561(9) 0.01569(18) Uani 1 1 d
N2 N 1.08589(15) 0.98506(13) 0.30917(12) 0.0244(2) Uani 1 1 d
C1 C 0.92528(14) 0.53990(12) 0.34651(10) 0.0146(2) Uani 1 1 d
C2 C 1.02347(16) 0.38957(13) 0.37340(11) 0.0176(2) Uani 1 1 d
C3 C 1.21831(16) 0.36617(14) 0.33002(11) 0.0202(2) Uani 1 1 d
C4 C 1.31483(16) 0.49131(14) 0.25921(11) 0.0201(2) Uani 1 1 d
C5 C 1.21574(16) 0.64055(14) 0.22891(11) 0.0190(2) Uani 1 1 d
C6 C 1.01991(15) 0.66737(12) 0.27261(11) 0.0154(2) Uani 1 1 d
C7 C 0.91288(15) 0.82909(13) 0.24200(11) 0.0163(2) Uani 1 1 d
C8 C 0.90969(16) 0.93710(13) 0.32787(12) 0.0196(2) Uani 1 1 d
C9 C 0.75623(16) 1.07475(13) 0.29215(12) 0.0194(2) Uani 1 1 d
C10 C 0.60112(16) 0.98974(13) 0.29988(12) 0.0178(2) Uani 1 1 d
C11 C 0.70126(14) 0.83524(12) 0.25759(10) 0.0144(2) Uani 1 1 d
C12 C 0.61286(15) 0.69697(12) 0.36395(10) 0.0147(2) Uani 1 1 d
C13 C 0.82290(16) 1.18228(14) 0.15353(12) 0.0215(2) Uani 1 1 d
C14 C 0.84379(18) 1.32840(15) 0.12900(14) 0.0260(3) Uani 1 1 d
C15 C 0.68631(15) 0.84275(12) 0.11863(11) 0.0164(2) Uani 1 1 d
C16 C 0.64935(18) 0.70615(15) -0.01895(12) 0.0209(2) Uani 1 1 d
H1 H 0.6719(19) 0.4828(16) 0.4556(14) 0.029(4) Uiso 1 1 d
H2 H 0.9539(17) 0.3045(15) 0.4204(13) 0.021(3) Uiso 1 1 d
H2A H 1.147(2) 1.0154(18) 0.2232(16) 0.040(4) Uiso 1 1 d
H2B H 1.166(2) 0.9042(19) 0.3473(16) 0.043(4) Uiso 1 1 d
H3 H 1.2833(17) 0.2615(15) 0.3504(12) 0.018(3) Uiso 1 1 d
H4 H 1.447(2) 0.4737(15) 0.2302(14) 0.029(4) Uiso 1 1 d
H5 H 1.2784(18) 0.7277(15) 0.1776(13) 0.026(4) Uiso 1 1 d
H7 H 0.9747(18) 0.8815(15) 0.1456(13) 0.024(3) Uiso 1 1 d
H8 H 0.8599(16) 0.8819(14) 0.4261(12) 0.014(3) Uiso 1 1 d
H9 H 0.7155(17) 1.1335(14) 0.3609(13) 0.019(3) Uiso 1 1 d
H10A H 0.5241(16) 1.0483(14) 0.2433(12) 0.015(3) Uiso 1 1 d
H10B H 0.5202(16) 0.9630(13) 0.3954(12) 0.014(3) Uiso 1 1 d
H13 H 0.8473(18) 1.1360(15) 0.0762(14) 0.028(4) Uiso 1 1 d
H14A H 0.8124(19) 1.3735(16) 0.2033(14) 0.032(4) Uiso 1 1 d
H14B H 0.8860(19) 1.3939(16) 0.0381(14) 0.028(4) Uiso 1 1 d
H16A H 0.5459(19) 0.7866(15) -0.0436(13) 0.024(3) Uiso 1 1 d
H16B H 0.6227(18) 0.6081(16) -0.0092(13) 0.022(3) Uiso 1 1 d
H16C H 0.7662(19) 0.7209(15) -0.0849(14) 0.025(4) 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
C15 O3 C16 115.23(9)
C12 N1 C1 125.72(9)
C12 N1 H1 116.1(9)
C1 N1 H1 118.1(9)
C8 N2 H2A 111.6(10)
C8 N2 H2B 111.6(9)
H2A N2 H2B 106.0(14)
C2 C1 C6 121.00(10)
C2 C1 N1 118.99(10)
C6 C1 N1 120.01(10)
C3 C2 C1 119.60(10)
C3 C2 H2 121.6(8)
C1 C2 H2 118.7(8)
C2 C3 C4 120.27(11)
C2 C3 H3 118.2(7)
C4 C3 H3 121.5(7)
C3 C4 C5 119.80(11)
C3 C4 H4 119.3(8)
C5 C4 H4 120.8(8)
C4 C5 C6 121.02(11)
C4 C5 H5 121.5(8)
C6 C5 H5 117.5(8)
C5 C6 C1 118.25(10)
C5 C6 C7 121.02(10)
C1 C6 C7 120.72(9)
C6 C7 C8 116.70(9)
C6 C7 C11 114.37(9)
C8 C7 C11 104.20(9)
C6 C7 H7 107.1(8)
C8 C7 H7 105.8(7)
C11 C7 H7 108.1(7)
N2 C8 C9 113.55(10)
N2 C8 C7 117.56(10)
C9 C8 C7 102.10(9)
N2 C8 H8 108.3(7)
C9 C8 H8 107.3(7)
C7 C8 H8 107.4(7)
C13 C9 C10 111.69(10)
C13 C9 C8 113.01(10)
C10 C9 C8 101.94(9)
C13 C9 H9 109.3(7)
C10 C9 H9 112.2(7)
C8 C9 H9 108.5(7)
C9 C10 C11 107.07(9)
C9 C10 H10A 113.9(7)
C11 C10 H10A 109.5(7)
C9 C10 H10B 109.0(7)
C11 C10 H10B 108.6(7)
H10A C10 H10B 108.6(10)
C15 C11 C12 109.43(9)
C15 C11 C7 107.53(8)
C12 C11 C7 114.40(9)
C15 C11 C10 110.87(9)
C12 C11 C10 110.03(9)
C7 C11 C10 104.48(8)
O1 C12 N1 121.40(10)
O1 C12 C11 120.58(9)
N1 C12 C11 118.01(9)
C14 C13 C9 125.48(12)
C14 C13 H13 120.0(8)
C9 C13 H13 114.5(8)
C13 C14 H14A 119.3(8)
C13 C14 H14B 122.8(8)
H14A C14 H14B 117.8(11)
O2 C15 O3 123.70(10)
O2 C15 C11 123.68(10)
O3 C15 C11 112.57(9)
O3 C16 H16A 110.0(8)
O3 C16 H16B 107.2(8)
H16A C16 H16B 108.9(11)
O3 C16 H16C 109.2(8)
H16A C16 H16C 112.1(11)
H16B C16 H16C 109.3(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C12 1.2396(13)
O2 C15 1.2129(13)
O3 C15 1.3331(13)
O3 C16 1.4571(14)
N1 C12 1.3493(14)
N1 C1 1.4101(14)
N1 H1 0.894(14)
N2 C8 1.4532(15)
N2 H2A 0.874(16)
N2 H2B 0.923(16)
C1 C2 1.3935(15)
C1 C6 1.3990(14)
C2 C3 1.3881(16)
C2 H2 0.958(12)
C3 C4 1.3862(17)
C3 H3 0.963(12)
C4 C5 1.3918(16)
C4 H4 0.941(14)
C5 C6 1.3954(15)
C5 H5 0.949(13)
C6 C7 1.5046(15)
C7 C8 1.5555(16)
C7 C11 1.5630(14)
C7 H7 1.000(13)
C8 C9 1.5509(16)
C8 H8 1.005(12)
C9 C13 1.5060(16)
C9 C10 1.5433(16)
C9 H9 0.980(13)
C10 C11 1.5665(15)
C10 H10A 0.948(12)
C10 H10B 0.995(12)
C11 C15 1.5308(15)
C11 C12 1.5333(14)
C13 C14 1.3213(17)
C13 H13 1.001(14)
C14 H14A 0.955(14)
C14 H14B 0.968(14)
C16 H16A 0.990(13)
C16 H16B 0.938(13)
C16 H16C 0.944(14)
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 O1 0.894(14) 2.029(14) 2.9217(12) 175.5(13) 2_666
N2 H2A O2 0.874(16) 2.483(16) 3.3366(15) 165.7(13) 2_775
N2 H2B O1 0.923(16) 2.576(16) 3.4855(13) 168.5(13) 1_655
