#------------------------------------------------------------------------------
#$Date: 2019-11-23 19:56:52 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234742 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/64/4036474.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_4036474
loop_
_publ_author_name
'Han, Wenyong'
'Zhou, Xiaojian'
'Yang, Siyi'
'Xiang, Guangyan'
'Cui, Baodong'
'Chen, Yongzheng'
_publ_section_title
;
 Palladium-Catalyzed Nucleophilic Substitution/C-H
 Activation/Aromatization Cascade Reaction: One Approach To Construct
 6-Unsubstituted Phenanthridines.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11580
_journal_page_last               11587
_journal_paper_doi               10.1021/acs.joc.5b02145
_journal_volume                  80
_journal_year                    2015
_chemical_formula_sum            'C17 H11 N'
_chemical_formula_weight         229.27
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 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                 98.661(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.1014(8)
_cell_length_b                   4.5936(5)
_cell_length_c                   17.649(2)
_cell_measurement_reflns_used    930
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.16
_cell_measurement_theta_min      2.33
_cell_volume                     569.16(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  CCD
_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  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3539
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9922
_exptl_absorpt_correction_T_min  0.9830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.090
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1042
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0376
_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)+(0.0503P)²+0.0462P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1043
_reflns_number_gt                795
_reflns_number_total             1042
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02145_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/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_cell_volume        569.15(11)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4036474
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_group
C1 C 0.4299(2) 0.5194(3) 0.32165(8) 0.0597(4) Uani 1 1 d . .
H1 H 0.3182 0.5597 0.2886 0.072 Uiso 1 1 calc R .
C2 C 0.5959(3) 0.6492(3) 0.31043(9) 0.0676(5) Uani 1 1 d . .
H2 H 0.5970 0.7783 0.2699 0.081 Uiso 1 1 calc R .
C3 C 0.7637(3) 0.5891(3) 0.35941(10) 0.0663(5) Uani 1 1 d . .
H3 H 0.8764 0.6787 0.3513 0.080 Uiso 1 1 calc R .
C4 C 0.7652(2) 0.3994(3) 0.41960(9) 0.0567(4) Uani 1 1 d . .
H4 H 0.8787 0.3611 0.4517 0.068 Uiso 1 1 calc R .
C5 C 0.59642(19) 0.2627(3) 0.43297(7) 0.0453(4) Uani 1 1 d . .
C6 C 0.4264(2) 0.3244(3) 0.38308(7) 0.0479(4) Uani 1 1 d . .
C7 C 0.58735(18) 0.0622(3) 0.49527(7) 0.0441(4) Uani 1 1 d . .
C8 C 0.75332(17) -0.0050(3) 0.54550(7) 0.0510(4) Uani 0.50 1 d P 1
H8 H 0.8690 0.0782 0.5388 0.061 Uiso 0.50 1 calc PR 1
N1 N 0.75332(17) -0.0050(3) 0.54550(7) 0.0510(4) Uani 0.50 1 d P 2
C9 C 0.2558(2) 0.1890(3) 0.39705(8) 0.0539(4) Uani 1 1 d . .
H9 H 0.1440 0.2310 0.3642 0.065 Uiso 1 1 calc R .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0705(11) 0.0588(9) 0.0476(8) -0.0005(7) 0.0017(7) 0.0136(8)
C2 0.0906(13) 0.0588(9) 0.0546(9) 0.0031(7) 0.0149(9) 0.0043(9)
C3 0.0738(12) 0.0596(9) 0.0690(10) -0.0103(8) 0.0224(9) -0.0065(8)
C4 0.0534(9) 0.0586(9) 0.0570(9) -0.0122(7) 0.0041(7) 0.0057(7)
C5 0.0484(8) 0.0449(7) 0.0417(7) -0.0113(6) 0.0041(6) 0.0093(6)
C6 0.0536(8) 0.0484(8) 0.0401(7) -0.0086(6) 0.0026(6) 0.0116(6)
C7 0.0423(7) 0.0476(7) 0.0400(7) -0.0116(6) -0.0011(6) 0.0116(6)
C8 0.0429(7) 0.0615(8) 0.0463(7) -0.0049(6) -0.0004(6) 0.0076(6)
N1 0.0429(7) 0.0615(8) 0.0463(7) -0.0049(6) -0.0004(6) 0.0076(6)
C9 0.0468(8) 0.0655(9) 0.0460(8) -0.0042(7) -0.0044(6) 0.0145(7)
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'
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
C2 C1 C6 120.42(15) . .
C1 C2 C3 120.15(15) . .
C4 C3 C2 120.87(16) . .
C3 C4 C5 120.44(14) . .
C4 C5 C6 118.49(13) . .
C4 C5 C7 123.41(13) . .
C6 C5 C7 118.10(13) . .
C1 C6 C5 119.63(14) . .
C1 C6 C9 121.88(13) . .
C5 C6 C9 118.49(13) . .
C8 C7 C7 120.79(16) . 3_656
C8 C7 C5 119.60(13) . .
C7 C7 C5 119.61(14) 3_656 .
C9 C8 C7 119.40(13) 3_656 .
N1 C9 C8 0.00(15) 3_656 3_656
N1 C9 C6 123.61(13) 3_656 .
C8 C9 C6 123.61(13) 3_656 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.361(2) .
C1 C6 1.410(2) .
C2 C3 1.390(2) .
C3 C4 1.373(2) .
C4 C5 1.404(2) .
C5 C6 1.4120(18) .
C5 C7 1.4430(19) .
C6 C9 1.416(2) .
C7 C8 1.3986(17) .
C7 C7 1.399(3) 3_656
C8 C9 1.3288(18) 3_656
C9 N1 1.3288(18) 3_656
C9 C8 1.3288(18) 3_656
