#------------------------------------------------------------------------------
#$Date: 2019-11-23 14:20:10 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233596 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/31/1553101.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_1553101
loop_
_publ_author_name
'Dethe, Dattatraya H.'
'Kumar B, Vijay'
_publ_section_title
;
 Concise asymmetric total synthesis of bruceolline J
;
_journal_issue                   5
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              548
_journal_paper_doi               10.1039/C5QO00030K
_journal_volume                  2
_journal_year                    2015
_chemical_formula_sum            'C18 H13 N O2'
_chemical_formula_weight         275.29
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-05-21 deposited with the CCDC.
2015-03-03 downloaded from the CCDC.
;
_cell_angle_alpha                78.846(5)
_cell_angle_beta                 82.356(5)
_cell_angle_gamma                72.557(5)
_cell_formula_units_Z            2
_cell_length_a                   7.159(5)
_cell_length_b                   9.364(5)
_cell_length_c                   10.541(5)
_cell_measurement_reflns_used    1098
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      2.79
_cell_volume                     659.3(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_sigmaI/netI    0.0342
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3408
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         4.09
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2278
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0535
_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)+(0.0992P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1428
_refine_ls_wR_factor_ref         0.1585
_reflns_number_gt                1712
_reflns_number_total             2278
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5qo00030k2.cif
_cod_data_source_block           22aprbm
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               1553101
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
_atom_site_refinement_flags
C1 C 0.2292(3) 0.2969(3) 0.4700(2) 0.0392(6) Uani 1 1 d .
H1 H 0.2443 0.3798 0.4091 0.047 Uiso 1 1 calc R
C2 C 0.1728(3) 0.3098(3) 0.5977(2) 0.0486(6) Uani 1 1 d .
H2 H 0.1509 0.4033 0.6236 0.058 Uiso 1 1 calc R
C3 C 0.1471(3) 0.1863(4) 0.6906(2) 0.0547(7) Uani 1 1 d .
H3 H 0.1081 0.2000 0.7762 0.066 Uiso 1 1 calc R
C4 C 0.1783(3) 0.0460(3) 0.6576(2) 0.0475(7) Uani 1 1 d .
H4 H 0.1602 -0.0350 0.7197 0.057 Uiso 1 1 calc R
C5 C 0.2387(3) 0.0269(3) 0.52719(18) 0.0375(6) Uani 1 1 d .
C6 C 0.2632(3) 0.1542(3) 0.43484(18) 0.0337(5) Uani 1 1 d .
C7 C 0.2853(3) -0.0967(3) 0.4581(2) 0.0377(5) Uani 1 1 d .
C8 C 0.3372(3) -0.0421(2) 0.33109(18) 0.0319(5) Uani 1 1 d .
C9 C 0.3922(3) -0.1584(2) 0.2507(2) 0.0339(5) Uani 1 1 d .
C10 C 0.3630(3) -0.3008(3) 0.3457(2) 0.0414(6) Uani 1 1 d .
C11 C 0.2931(3) -0.2610(3) 0.4802(2) 0.0442(6) Uani 1 1 d .
H11A H 0.1648 -0.2759 0.5085 0.053 Uiso 1 1 calc R
H11B H 0.3854 -0.3202 0.5433 0.053 Uiso 1 1 calc R
C12 C 0.3348(3) 0.2090(2) 0.19065(17) 0.0332(5) Uani 1 1 d .
H12A H 0.4300 0.1544 0.1296 0.040 Uiso 1 1 calc R
H12B H 0.3766 0.2949 0.2018 0.040 Uiso 1 1 calc R
C13 C 0.1354(3) 0.2650(2) 0.13692(17) 0.0295(5) Uani 1 1 d .
C14 C -0.0008(4) 0.3972(2) 0.1669(2) 0.0420(6) Uani 1 1 d .
H14 H 0.0338 0.4566 0.2158 0.050 Uiso 1 1 calc R
C15 C -0.1876(4) 0.4412(3) 0.1246(2) 0.0497(7) Uani 1 1 d .
H15 H -0.2783 0.5294 0.1458 0.060 Uiso 1 1 calc R
C16 C -0.2393(3) 0.3539(3) 0.0508(2) 0.0460(6) Uani 1 1 d .
H16 H -0.3650 0.3830 0.0228 0.055 Uiso 1 1 calc R
C17 C -0.1036(3) 0.2233(2) 0.0189(2) 0.0384(5) Uani 1 1 d .
H17 H -0.1379 0.1650 -0.0313 0.046 Uiso 1 1 calc R
C18 C 0.0830(3) 0.1792(2) 0.06145(18) 0.0327(5) Uani 1 1 d .
H18 H 0.1739 0.0915 0.0394 0.039 Uiso 1 1 calc R
N1 N 0.3281(2) 0.10854(19) 0.31590(15) 0.0315(4) Uani 1 1 d .
O1 O 0.4489(2) -0.15782(16) 0.13603(14) 0.0398(4) Uani 1 1 d .
O2 O 0.3929(2) -0.42222(19) 0.31173(18) 0.0559(5) 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 0.0016 '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
C2 C1 C6 117.4(2)
C1 C2 C3 122.1(2)
C4 C3 C2 121.3(2)
C3 C4 C5 118.7(2)
C4 C5 C7 134.9(2)
C4 C5 C6 118.9(2)
C7 C5 C6 106.21(18)
N1 C6 C1 129.33(19)
N1 C6 C5 108.92(19)
C1 C6 C5 121.72(19)
C8 C7 C5 106.7(2)
C8 C7 C11 113.3(2)
C5 C7 C11 140.04(19)
N1 C8 C7 111.08(19)
N1 C8 C9 136.77(17)
C7 C8 C9 112.1(2)
O1 C9 C8 132.58(19)
O1 C9 C10 124.1(2)
C8 C9 C10 103.33(18)
O2 C10 C11 127.6(2)
O2 C10 C9 122.5(2)
C11 C10 C9 109.96(19)
C7 C11 C10 101.27(17)
N1 C12 C13 110.78(15)
C14 C13 C18 119.1(2)
C14 C13 C12 121.30(18)
C18 C13 C12 119.57(18)
C15 C14 C13 120.6(2)
C14 C15 C16 119.9(2)
C17 C16 C15 119.9(2)
C16 C17 C18 120.1(2)
C17 C18 C13 120.38(19)
C8 N1 C6 107.08(16)
C8 N1 C12 125.07(16)
C6 N1 C12 126.00(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.371(3)
C1 C6 1.398(3)
C2 C3 1.404(4)
C3 C4 1.370(4)
C4 C5 1.414(3)
C5 C7 1.418(3)
C5 C6 1.425(3)
C6 N1 1.380(3)
C7 C8 1.382(3)
C7 C11 1.496(3)
C8 N1 1.371(3)
C8 C9 1.439(3)
C9 O1 1.222(2)
C9 C10 1.555(3)
C10 O2 1.208(3)
C10 C11 1.517(3)
C12 N1 1.469(2)
C12 C13 1.512(3)
C13 C14 1.388(3)
C13 C18 1.389(3)
C14 C15 1.383(3)
C15 C16 1.384(4)
C16 C17 1.383(3)
C17 C18 1.383(3)
