#------------------------------------------------------------------------------
#$Date: 2016-03-21 05:33:32 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178484 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/05/4030558.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_4030558
loop_
_publ_author_name
'Feng, Xian'
'Wang, Jian-Jun'
'Xun, Zhan'
'Huang, Zhi-Bin'
'Shi, Da-Qing'
_publ_section_title
;
 Multicomponent Strategy to Indeno[2,1-c]pyridine and Hydroisoquinoline
 Derivatives through Cleavage of Carbon-Carbon Bond.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1025
_journal_paper_doi               10.1021/jo5025199
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C19 H14 Br N3 O2'
_chemical_formula_weight         396.24
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.3100(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.3184(13)
_cell_length_b                   7.1606(5)
_cell_length_c                   17.5832(18)
_cell_measurement_reflns_used    1146
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.096
_cell_measurement_theta_min      3.073
_cell_volume                     1672.1(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0991
_diffrn_reflns_av_sigmaI/netI    0.1120
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8185
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.69
_exptl_absorpt_coefficient_mu    2.476
_exptl_absorpt_correction_T_max  0.6642
_exptl_absorpt_correction_T_min  0.5545
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            cloroless
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.687
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2944
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1494
_refine_ls_R_factor_gt           0.0667
_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)+(0.0611P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1515
_refine_ls_wR_factor_ref         0.1708
_reflns_number_gt                1247
_reflns_number_total             2944
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5025199_si_002.cif
_cod_data_source_block           131121b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4030558
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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
Br1 Br 0.68762(5) 1.40163(15) 0.59390(5) 0.1025(5) Uani 1 1 d .
N1 N 0.2625(3) 1.4015(7) 0.6978(3) 0.0476(14) Uani 1 1 d .
N2 N 0.2005(3) 1.4073(8) 0.5705(3) 0.0600(16) Uani 1 1 d .
H2A H 0.2616 1.4020 0.5579 0.072 Uiso 1 1 calc R
H2B H 0.1516 1.4116 0.5358 0.072 Uiso 1 1 calc R
N3 N -0.0653(4) 1.4237(9) 0.5673(3) 0.0671(18) Uani 1 1 d .
O1 O 0.3298(3) 1.3921(7) 0.8216(2) 0.0643(14) Uani 1 1 d .
O2 O 0.3889(11) 1.419(2) 0.9958(5) 0.411(13) Uani 1 1 d .
H2D H 0.3935 1.3377 0.9611 0.494 Uiso 1 1 d R
H2E H 0.3630 1.4954 0.9627 0.494 Uiso 1 1 d R
C1 C 0.2516(4) 1.4018(9) 0.7787(4) 0.0486(17) Uani 1 1 d .
C2 C 0.1528(4) 1.4063(9) 0.7994(3) 0.0439(16) Uani 1 1 d .
C3 C 0.0714(4) 1.4130(9) 0.7462(3) 0.0436(16) Uani 1 1 d .
C4 C 0.0843(4) 1.4136(8) 0.6675(3) 0.0418(16) Uani 1 1 d .
C5 C 0.1819(4) 1.4087(9) 0.6431(4) 0.0467(17) Uani 1 1 d .
C6 C 0.1193(4) 1.4046(10) 0.8789(3) 0.0550(18) Uani 1 1 d .
H6A H 0.1425 1.5149 0.9069 0.066 Uiso 1 1 calc R
H6B H 0.1435 1.2942 0.9065 0.066 Uiso 1 1 calc R
C7 C 0.0064(4) 1.4030(9) 0.8655(3) 0.0486(17) Uani 1 1 d .
C8 C -0.0206(4) 1.4125(9) 0.7862(3) 0.0424(16) Uani 1 1 d .
C9 C -0.1208(4) 1.4173(9) 0.7594(4) 0.0492(17) Uani 1 1 d .
H9 H -0.1393 1.4260 0.7075 0.059 Uiso 1 1 calc R
C10 C -0.1918(4) 1.4090(10) 0.8113(4) 0.062(2) Uani 1 1 d .
H10 H -0.2595 1.4097 0.7939 0.075 Uiso 1 1 calc R
C11 C -0.1666(5) 1.3995(10) 0.8888(5) 0.069(2) Uani 1 1 d .
H11 H -0.2171 1.3947 0.9225 0.083 Uiso 1 1 calc R
C12 C -0.0662(5) 1.3971(10) 0.9168(4) 0.064(2) Uani 1 1 d .
H12 H -0.0487 1.3917 0.9689 0.077 Uiso 1 1 calc R
C13 C 0.3641(4) 1.4049(12) 0.6738(4) 0.0519(18) Uani 1 1 d .
C14 C 0.4233(5) 1.2498(12) 0.6839(4) 0.078(2) Uani 1 1 d .
H14 H 0.3986 1.1431 0.7062 0.094 Uiso 1 1 calc R
C15 C 0.5202(5) 1.2525(15) 0.6606(5) 0.095(3) Uani 1 1 d .
H15 H 0.5613 1.1480 0.6680 0.114 Uiso 1 1 calc R
C16 C 0.5552(4) 1.4065(15) 0.6274(4) 0.070(2) Uani 1 1 d .
C17 C 0.4990(5) 1.5617(13) 0.6192(5) 0.084(3) Uani 1 1 d .
H17 H 0.5252 1.6691 0.5985 0.101 Uiso 1 1 calc R
C18 C 0.4027(5) 1.5606(11) 0.6417(4) 0.069(2) Uani 1 1 d .
H18 H 0.3630 1.6670 0.6349 0.083 Uiso 1 1 calc R
C19 C 0.0027(4) 1.4194(9) 0.6109(3) 0.0471(17) 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'
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 '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
C5 N1 C1 123.6(5)
C5 N1 C13 119.3(5)
C1 N1 C13 117.0(5)
C5 N2 H2A 120.0
C5 N2 H2B 120.0
H2A N2 H2B 120.0
H2D O2 H2E 89.9
O1 C1 C2 127.5(6)
O1 C1 N1 117.2(5)
C2 C1 N1 115.2(5)
C3 C2 C1 122.3(5)
C3 C2 C6 111.1(5)
C1 C2 C6 126.7(5)
C2 C3 C4 121.3(5)
C2 C3 C8 108.6(5)
C4 C3 C8 130.1(5)
C5 C4 C3 119.1(5)
C5 C4 C19 117.8(5)
C3 C4 C19 123.1(5)
N2 C5 N1 118.6(5)
N2 C5 C4 122.9(5)
N1 C5 C4 118.4(5)
C2 C6 C7 102.6(5)
C2 C6 H6A 111.2
C7 C6 H6A 111.2
C2 C6 H6B 111.2
C7 C6 H6B 111.2
H6A C6 H6B 109.2
C12 C7 C8 120.6(5)
C12 C7 C6 130.1(6)
C8 C7 C6 109.3(5)
C9 C8 C7 120.3(5)
C9 C8 C3 131.3(6)
C7 C8 C3 108.4(5)
C10 C9 C8 118.1(6)
C10 C9 H9 120.9
C8 C9 H9 120.9
C9 C10 C11 122.2(6)
C9 C10 H10 118.9
C11 C10 H10 118.9
C10 C11 C12 120.4(6)
C10 C11 H11 119.8
C12 C11 H11 119.8
C7 C12 C11 118.3(6)
C7 C12 H12 120.8
C11 C12 H12 120.8
C14 C13 C18 119.0(6)
C14 C13 N1 119.5(7)
C18 C13 N1 121.5(6)
C13 C14 C15 119.5(8)
C13 C14 H14 120.2
C15 C14 H14 120.2
C16 C15 C14 120.1(8)
C16 C15 H15 120.0
C14 C15 H15 120.0
C17 C16 C15 121.1(7)
C17 C16 Br1 120.3(7)
C15 C16 Br1 118.6(7)
C16 C17 C18 119.4(8)
C16 C17 H17 120.3
C18 C17 H17 120.3
C13 C18 C17 120.8(7)
C13 C18 H18 119.6
C17 C18 H18 119.6
N3 C19 C4 177.7(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C16 1.901(6)
N1 C5 1.388(7)
N1 C1 1.441(7)
N1 C13 1.447(7)
N2 C5 1.317(7)
N2 H2A 0.8600
N2 H2B 0.8600
N3 C19 1.143(7)
O1 C1 1.242(6)
O2 H2D 0.8505
O2 H2E 0.8504
C1 C2 1.392(7)
C2 C3 1.378(7)
C2 C6 1.499(8)
C3 C4 1.407(8)
C3 C8 1.457(7)
C4 C5 1.400(7)
C4 C19 1.418(8)
C6 C7 1.504(7)
C6 H6A 0.9700
C6 H6B 0.9700
C7 C12 1.371(8)
C7 C8 1.415(8)
C8 C9 1.383(7)
C9 C10 1.363(8)
C9 H9 0.9300
C10 C11 1.379(9)
C10 H10 0.9300
C11 C12 1.390(8)
C11 H11 0.9300
C12 H12 0.9300
C13 C14 1.366(9)
C13 C18 1.368(9)
C14 C15 1.383(9)
C14 H14 0.9300
C15 C16 1.347(11)
C15 H15 0.9300
C16 C17 1.341(10)
C17 C18 1.371(9)
C17 H17 0.9300
C18 H18 0.9300
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
C5 N1 C1 O1 179.0(6)
C13 N1 C1 O1 -4.7(9)
C5 N1 C1 C2 1.1(9)
C13 N1 C1 C2 177.5(6)
O1 C1 C2 C3 -178.5(7)
N1 C1 C2 C3 -1.0(9)
O1 C1 C2 C6 1.5(12)
N1 C1 C2 C6 179.0(6)
C1 C2 C3 C4 0.7(10)
C6 C2 C3 C4 -179.3(6)
C1 C2 C3 C8 178.9(6)
C6 C2 C3 C8 -1.1(8)
C2 C3 C4 C5 -0.5(10)
C8 C3 C4 C5 -178.2(7)
C2 C3 C4 C19 179.6(6)
C8 C3 C4 C19 1.9(11)
C1 N1 C5 N2 -179.8(6)
C13 N1 C5 N2 3.9(9)
C1 N1 C5 C4 -1.0(9)
C13 N1 C5 C4 -177.2(6)
C3 C4 C5 N2 179.4(6)
C19 C4 C5 N2 -0.7(10)
C3 C4 C5 N1 0.6(9)
C19 C4 C5 N1 -179.5(5)
C3 C2 C6 C7 2.3(7)
C1 C2 C6 C7 -177.7(7)
C2 C6 C7 C12 178.5(7)
C2 C6 C7 C8 -2.7(7)
C12 C7 C8 C9 0.5(10)
C6 C7 C8 C9 -178.5(6)
C12 C7 C8 C3 -178.8(6)
C6 C7 C8 C3 2.2(8)
C2 C3 C8 C9 -179.9(7)
C4 C3 C8 C9 -1.9(12)
C2 C3 C8 C7 -0.7(8)
C4 C3 C8 C7 177.3(6)
C7 C8 C9 C10 -1.3(10)
C3 C8 C9 C10 177.8(7)
C8 C9 C10 C11 1.2(11)
C9 C10 C11 C12 -0.4(12)
C8 C7 C12 C11 0.4(11)
C6 C7 C12 C11 179.2(7)
C10 C11 C12 C7 -0.5(12)
C5 N1 C13 C14 -112.3(7)
C1 N1 C13 C14 71.2(8)
C5 N1 C13 C18 68.1(9)
C1 N1 C13 C18 -108.4(7)
C18 C13 C14 C15 -0.7(11)
N1 C13 C14 C15 179.6(7)
C13 C14 C15 C16 -0.9(13)
C14 C15 C16 C17 2.9(13)
C14 C15 C16 Br1 -178.4(6)
C15 C16 C17 C18 -3.2(13)
Br1 C16 C17 C18 178.1(6)
C14 C13 C18 C17 0.4(11)
N1 C13 C18 C17 -180.0(6)
C16 C17 C18 C13 1.5(12)
C5 C4 C19 N3 176(100)
C3 C4 C19 N3 -4(18)
