#------------------------------------------------------------------------------
#$Date: 2017-01-09 06:31:22 +0200 (Mon, 09 Jan 2017) $
#$Revision: 190224 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/68/7226889.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_7226889
loop_
_publ_author_name
'Senadi, Gopal Chandru'
'Dhandabani, Ganesh Kumar'
'Hu, Wan-Ping'
'Wang, Jeh-Jeng'
_publ_section_title
;
 Metal-free annulation/aerobic oxidative dehydrogenation of cyclohexanones
 with o-acylanilines: efficient syntheses of acridines
;
_journal_issue                   23
_journal_name_full               'Green Chem.'
_journal_page_first              6241
_journal_paper_doi               10.1039/C6GC02396G
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C19 H13 N'
_chemical_formula_sum            'C19 H13 N'
_chemical_formula_weight         255.30
_space_group_crystal_system      monoclinic
_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_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-08-19 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.345(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4892(6)
_cell_length_b                   17.7731(15)
_cell_length_c                   9.0884(7)
_cell_measurement_reflns_used    1020
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.5770
_cell_measurement_theta_min      3.3970
_cell_volume                     1308.90(18)
_computing_cell_refinement
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_collection
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.843
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0755
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6020
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.324
_diffrn_reflns_theta_min         2.763
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) 
(compiled Jan 14 2014,18:38:05) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3031
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1114
_refine_ls_R_factor_gt           0.0639
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0566P)²+0.0496P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1479
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1885
_reflns_number_total             3031
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6gc02396g2.cif
_cod_data_source_block           g1063
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7226889--7226892.cif.
;
_cod_original_cell_volume        1308.89(18)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7226889
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N N -0.21711(19) 0.13981(10) 0.03014(19) 0.0271(4) Uani 1 1 d . .
C1 C -0.2340(2) 0.15445(12) 0.1701(2) 0.0251(5) Uani 1 1 d . .
C2 C -0.3898(2) 0.18129(12) 0.1768(2) 0.0312(5) Uani 1 1 d . .
H2A H -0.4787 0.1857 0.0845 0.037 Uiso 1 1 calc R U
C3 C -0.4130(2) 0.20067(13) 0.3132(3) 0.0355(6) Uani 1 1 d . .
H3A H -0.5172 0.2194 0.3152 0.043 Uiso 1 1 calc R U
C4 C -0.2831(2) 0.19319(13) 0.4528(3) 0.0330(5) Uani 1 1 d . .
H4A H -0.3008 0.2070 0.5476 0.040 Uiso 1 1 calc R U
C5 C -0.1333(2) 0.16630(12) 0.4520(2) 0.0283(5) Uani 1 1 d . .
H5A H -0.0480 0.1608 0.5467 0.034 Uiso 1 1 calc R U
C6 C -0.1022(2) 0.14622(11) 0.3109(2) 0.0225(5) Uani 1 1 d . .
C7 C 0.0506(2) 0.11936(12) 0.3029(2) 0.0225(5) Uani 1 1 d . .
C8 C 0.0706(2) 0.10515(11) 0.1577(2) 0.0225(5) Uani 1 1 d . .
C9 C 0.2228(2) 0.08113(12) 0.1360(2) 0.0282(5) Uani 1 1 d . .
H9A H 0.3161 0.0734 0.2233 0.034 Uiso 1 1 calc R U
C10 C 0.2362(3) 0.06914(13) -0.0069(2) 0.0323(5) Uani 1 1 d . .
H10A H 0.3387 0.0533 -0.0187 0.039 Uiso 1 1 calc R U
C11 C 0.0980(3) 0.08005(13) -0.1395(2) 0.0332(5) Uani 1 1 d . .
H11A H 0.1087 0.0709 -0.2390 0.040 Uiso 1 1 calc R U
C12 C -0.0495(2) 0.10348(12) -0.1251(2) 0.0297(5) Uani 1 1 d . .
H12A H -0.1405 0.1110 -0.2147 0.036 Uiso 1 1 calc R U
C13 C -0.0681(2) 0.11669(12) 0.0230(2) 0.0249(5) Uani 1 1 d . .
C14 C 0.1910(2) 0.10522(12) 0.4458(2) 0.0225(5) Uani 1 1 d . .
C15 C 0.2805(2) 0.16457(13) 0.5308(2) 0.0279(5) Uani 1 1 d . .
H15A H 0.2516 0.2149 0.4990 0.033 Uiso 1 1 calc R U
C16 C 0.4119(2) 0.15052(14) 0.6619(2) 0.0317(5) Uani 1 1 d . .
H16A H 0.4721 0.1914 0.7195 0.038 Uiso 1 1 calc R U
C17 C 0.4553(2) 0.07762(14) 0.7088(2) 0.0315(6) Uani 1 1 d . .
H17A H 0.5460 0.0683 0.7977 0.038 Uiso 1 1 calc R U
C18 C 0.3668(2) 0.01827(14) 0.6263(2) 0.0315(5) Uani 1 1 d . .
H18A H 0.3959 -0.0319 0.6592 0.038 Uiso 1 1 calc R U
C19 C 0.2348(2) 0.03175(13) 0.4948(2) 0.0280(5) Uani 1 1 d . .
H19A H 0.1745 -0.0093 0.4383 0.034 Uiso 1 1 calc R U
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
C1 N C13 118.00(16)
N C1 C2 117.82(18)
N C1 C6 123.26(17)
C2 C1 C6 118.91(19)
C3 C2 C1 120.94(19)
C3 C2 H2A 119.5
C1 C2 H2A 119.5
C2 C3 C4 120.52(19)
C2 C3 H3A 119.7
C4 C3 H3A 119.7
C5 C4 C3 120.5(2)
C5 C4 H4A 119.8
C3 C4 H4A 119.8
C4 C5 C6 121.01(19)
C4 C5 H5A 119.5
C6 C5 H5A 119.5
C7 C6 C5 123.46(17)
C7 C6 C1 118.41(18)
C5 C6 C1 118.13(17)
C6 C7 C8 118.83(17)
C6 C7 C14 121.40(18)
C8 C7 C14 119.78(16)
C7 C8 C9 123.47(17)
C7 C8 C13 118.52(17)
C9 C8 C13 118.00(17)
C10 C9 C8 121.19(18)
C10 C9 H9A 119.4
C8 C9 H9A 119.4
C9 C10 C11 120.44(19)
C9 C10 H10A 119.8
C11 C10 H10A 119.8
C12 C11 C10 120.68(19)
C12 C11 H11A 119.7
C10 C11 H11A 119.7
C11 C12 C13 120.41(18)
C11 C12 H12A 119.8
C13 C12 H12A 119.8
N C13 C12 117.80(17)
N C13 C8 122.92(18)
C12 C13 C8 119.28(17)
C19 C14 C15 118.89(18)
C19 C14 C7 120.10(18)
C15 C14 C7 121.00(19)
C14 C15 C16 120.3(2)
C14 C15 H15A 119.8
C16 C15 H15A 119.8
C17 C16 C15 120.4(2)
C17 C16 H16A 119.8
C15 C16 H16A 119.8
C18 C17 C16 119.89(19)
C18 C17 H17A 120.1
C16 C17 H17A 120.1
C17 C18 C19 120.2(2)
C17 C18 H18A 119.9
C19 C18 H18A 119.9
C14 C19 C18 120.3(2)
C14 C19 H19A 119.8
C18 C19 H19A 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N C1 1.347(2)
N C13 1.350(2)
C1 C2 1.424(3)
C1 C6 1.434(3)
C2 C3 1.356(3)
C2 H2A 0.9500
C3 C4 1.418(3)
C3 H3A 0.9500
C4 C5 1.361(3)
C4 H4A 0.9500
C5 C6 1.429(3)
C5 H5A 0.9500
C6 C7 1.405(3)
C7 C8 1.403(3)
C7 C14 1.499(3)
C8 C9 1.429(3)
C8 C13 1.438(3)
C9 C10 1.354(3)
C9 H9A 0.9500
C10 C11 1.422(3)
C10 H10A 0.9500
C11 C12 1.362(3)
C11 H11A 0.9500
C12 C13 1.421(3)
C12 H12A 0.9500
C14 C19 1.394(3)
C14 C15 1.391(3)
C15 C16 1.391(3)
C15 H15A 0.9500
C16 C17 1.379(3)
C16 H16A 0.9500
C17 C18 1.379(3)
C17 H17A 0.9500
C18 C19 1.394(3)
C18 H18A 0.9500
C19 H19A 0.9500
