#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:36:29 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179588 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/53/4505384.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_4505384
loop_
_publ_author_name
'Mei, Xuefeng'
'Wolf, Christian'
_publ_section_title
;
 Formation of New Polymorphs of Acridine Using Dicarboxylic Acids as
 Crystallization Templates in Solution
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1099
_journal_paper_doi               10.1021/cg0498655
_journal_volume                  4
_journal_year                    2004
_chemical_formula_moiety         'C13 H9 N'
_chemical_formula_sum            'C13 H9 N'
_chemical_formula_weight         179.21
_chemical_name_common            acridine
_chemical_name_systematic        acridine
_space_group_IT_number           14
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.938(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   6.0569(10)
_cell_length_b                   22.813(4)
_cell_length_c                   13.204(2)
_cell_measurement_reflns_used    936
_cell_measurement_temperature    185(2)
_cell_measurement_theta_max      27.987
_cell_measurement_theta_min      2.363
_cell_volume                     1814.7(5)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'SMART, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics    'XSEED, L. Barbour (1999); http:\x-seed.net'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      185(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'SMART platform CCD, Siemens/Bruker'
_diffrn_measurement_method       '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  0.0459
_diffrn_reflns_av_sigmaI/netI    0.0545
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14835
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9773
_exptl_absorpt_correction_T_min  0.9625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, G. Sheldrick (1999)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4251
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.0572
_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)+(0.0764P)²+0.0081P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1479
_reflns_number_gt                2562
_reflns_number_total             4251
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0498655si20040805_093625.cif
_cod_data_source_block
c:\docume~1\wolfuser\mydocu~1\xuefeng\x-rayd~1\04014\work\p21onn
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_original_cell_volume        1814.6(5)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4505384
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
N1 N 0.1696(2) 0.30681(6) 1.16081(11) 0.0307(4) Uani 1 1 d .
N1' N 0.2522(2) 0.01039(6) 0.89474(11) 0.0285(4) Uani 1 1 d .
C1 C 0.6956(3) 0.39169(8) 1.16900(14) 0.0324(4) Uani 1 1 d .
H1 H 0.8361 0.3953 1.2078 0.039 Uiso 1 1 calc R
C1' C 0.5669(3) 0.14402(8) 0.98422(14) 0.0337(5) Uani 1 1 d .
H1' H 0.7003 0.1645 0.9756 0.040 Uiso 1 1 calc R
C2 C 0.6477(3) 0.42552(8) 1.08512(15) 0.0361(5) Uani 1 1 d .
H2 H 0.7545 0.4527 1.0658 0.043 Uiso 1 1 calc R
C2' C 0.4267(3) 0.16563(8) 1.04837(15) 0.0381(5) Uani 1 1 d .
H2' H 0.4609 0.2014 1.0833 0.046 Uiso 1 1 calc R
C3 C 0.4398(3) 0.42059(8) 1.02625(14) 0.0364(5) Uani 1 1 d .
H3 H 0.4081 0.4446 0.9678 0.044 Uiso 1 1 calc R
C3' C 0.2282(3) 0.13498(8) 1.06378(14) 0.0366(5) Uani 1 1 d .
H3' H 0.1318 0.1504 1.1096 0.044 Uiso 1 1 calc R
C4 C 0.2850(3) 0.38195(8) 1.05214(14) 0.0337(5) Uani 1 1 d .
H4 H 0.1459 0.3795 1.0119 0.040 Uiso 1 1 calc R
C4' C 0.1743(3) 0.08398(8) 1.01401(13) 0.0325(5) Uani 1 1 d .
H4' H 0.0419 0.0639 1.0258 0.039 Uiso 1 1 calc R
C5 C 0.0423(3) 0.23460(8) 1.27125(15) 0.0367(5) Uani 1 1 d .
H5 H -0.0905 0.2304 1.2268 0.044 Uiso 1 1 calc R
C5' C 0.3237(3) -0.06433(8) 0.77612(14) 0.0337(4) Uani 1 1 d .
H5' H 0.1881 -0.0829 0.7875 0.040 Uiso 1 1 calc R
C6 C 0.0703(4) 0.20299(8) 1.35888(16) 0.0430(5) Uani 1 1 d .
H6 H -0.0444 0.1774 1.3754 0.052 Uiso 1 1 calc R
C6' C 0.4546(3) -0.08829(9) 0.71030(14) 0.0380(5) Uani 1 1 d .
H6' H 0.4107 -0.1240 0.6770 0.046 Uiso 1 1 calc R
C7 C 0.2676(4) 0.20753(8) 1.42605(16) 0.0411(5) Uani 1 1 d .
H7 H 0.2830 0.1855 1.4874 0.049 Uiso 1 1 calc R
C7' C 0.6562(3) -0.06123(9) 0.69001(14) 0.0402(5) Uani 1 1 d .
H7' H 0.7447 -0.0785 0.6426 0.048 Uiso 1 1 calc R
C8 C 0.4338(3) 0.24298(8) 1.40336(14) 0.0358(5) Uani 1 1 d .
H8 H 0.5667 0.2449 1.4483 0.043 Uiso 1 1 calc R
C8' C 0.7228(3) -0.01073(8) 0.73820(14) 0.0344(5) Uani 1 1 d .
H8' H 0.8579 0.0072 0.7241 0.041 Uiso 1 1 calc R
C9 C 0.5746(3) 0.31622(7) 1.28682(14) 0.0305(4) Uani 1 1 d .
H9 H 0.7115 0.3192 1.3287 0.037 Uiso 1 1 calc R
C9' C 0.6531(3) 0.06696(8) 0.86183(13) 0.0295(4) Uani 1 1 d .
H9' H 0.7888 0.0858 0.8512 0.035 Uiso 1 1 calc R
C10 C 0.5371(3) 0.35068(7) 1.19963(13) 0.0279(4) Uani 1 1 d .
C10' C 0.5175(3) 0.09117(8) 0.92949(13) 0.0274(4) Uani 1 1 d .
C11 C 0.3282(3) 0.34494(8) 1.13894(13) 0.0282(4) Uani 1 1 d .
C11' C 0.3152(3) 0.06038(8) 0.94430(12) 0.0264(4) Uani 1 1 d .
C12 C 0.2102(3) 0.27387(8) 1.24558(13) 0.0296(4) Uani 1 1 d .
C12' C 0.3871(3) -0.01142(8) 0.82870(13) 0.0270(4) Uani 1 1 d .
C13 C 0.4129(3) 0.27771(7) 1.31256(13) 0.0296(4) Uani 1 1 d .
C13' C 0.5932(3) 0.01580(8) 0.80961(13) 0.0279(4) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C11 N1 C12 117.63(16)
C11' N1' C12' 117.70(15)
C2 C1 C10 120.69(18)
C2' C1' C10' 120.99(18)
C1 C2 C3 120.44(18)
C1' C2' C3' 120.30(19)
C4 C3 C2 120.84(18)
C4' C3' C2' 121.01(18)
C3 C4 C11 120.90(18)
C3' C4' C11' 120.41(18)
C6 C5 C12 120.50(19)
C6' C5' C12' 120.66(18)
C5 C6 C7 121.16(19)
C5' C6' C7' 121.28(19)
C8 C7 C6 120.36(19)
C8' C7' C6' 120.06(18)
C7 C8 C13 120.95(19)
C7' C8' C13' 120.92(18)
C13 C9 C10 120.14(17)
C13' C9' C10' 120.88(17)
C9 C10 C1 123.13(17)
C9 C10 C11 118.03(17)
C1 C10 C11 118.84(17)
C9' C10' C1' 123.85(17)
C9' C10' C11' 117.42(17)
C1' C10' C11' 118.73(17)
N1 C11 C4 118.58(16)
N1 C11 C10 123.14(16)
C4 C11 C10 118.27(17)
N1' C11' C4' 118.31(16)
N1' C11' C10' 123.15(16)
C4' C11' C10' 118.54(17)
N1 C12 C5 118.35(17)
N1 C12 C13 123.12(17)
C5 C12 C13 118.51(17)
N1' C12' C5' 118.46(16)
N1' C12' C13' 123.20(17)
C5' C12' C13' 118.34(17)
C9 C13 C8 123.60(17)
C9 C13 C12 117.90(16)
C8 C13 C12 118.47(17)
C9' C13' C8' 123.65(17)
C9' C13' C12' 117.64(17)
C8' C13' C12' 118.72(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C11 1.349(2)
N1 C12 1.349(2)
N1' C11' 1.350(2)
N1' C12' 1.350(2)
C1 C2 1.356(3)
C1 C10 1.429(3)
C1' C2' 1.353(3)
C1' C10' 1.421(2)
C2 C3 1.414(3)
C2' C3' 1.424(3)
C3 C4 1.356(3)
C3' C4' 1.359(3)
C4 C11 1.426(3)
C4' C11' 1.424(2)
C5 C6 1.359(3)
C5 C12 1.422(3)
C5' C6' 1.351(3)
C5' C12' 1.425(2)
C6 C7 1.416(3)
C6' C7' 1.418(3)
C7 C8 1.349(3)
C7' C8' 1.357(3)
C8 C13 1.432(2)
C8' C13' 1.423(2)
C9 C13 1.384(3)
C9 C10 1.393(2)
C9' C13' 1.385(2)
C9' C10' 1.389(2)
C10 C11 1.432(2)
C10' C11' 1.443(2)
C12 C13 1.440(2)
C12' C13' 1.440(2)
