#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/57/4025720.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_4025720
loop_
_publ_author_name
'Marwan W. Ghosn'
'Christian Wolf'
_publ_contact_author             'Wolf, C.'
_publ_contact_author_email       cw27@georgetown.edu
_publ_section_title
;
 Stereocontrolled Photodimerization with Congested
 1,8-Bis(4'-anilino)naphthalene Templates
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6653
_journal_page_last               6659
_journal_paper_doi               10.1021/jo101547w
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C29 H22 N2 O2'
_chemical_formula_weight         430.49
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_space_group_name_Hall  '-P 1'
_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
_cell_angle_alpha                100.867(3)
_cell_angle_beta                 110.309(3)
_cell_angle_gamma                98.418(3)
_cell_formula_units_Z            2
_cell_length_a                   9.5279(15)
_cell_length_b                   10.4512(16)
_cell_length_c                   12.1116(19)
_cell_measurement_reflns_used    1762
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.179
_cell_measurement_theta_min      4.682
_cell_volume                     1081.0(3)
_computing_cell_refinement       'SAINT, Bruker-AXS'
_computing_data_collection       'APEX2, Bruker-AXS'
_computing_data_reduction        'SAINT, Bruker-AXS'
_computing_molecular_graphics    'X-SEED, L.Barbour (1999);http://x-seed.net/'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Siemens, SMART 1000 CCD'
_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  0.0567
_diffrn_reflns_av_sigmaI/netI    0.0933
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8238
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         1.86
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, G. Scheldrick (1999)'
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3800
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1167
_refine_ls_R_factor_gt           0.0599
_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)+(0.0433P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1221
_reflns_number_gt                2245
_reflns_number_total             3800
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101547w_si_003.cif
_cod_data_source_block           compoundshortname
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity' tag as specified in the
replacement file
'/home/andrius/src/cod-tools/trunk/tests/inputs/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 4372 2015-11-25 23:04:01Z antanas 
;
_cod_database_code               4025720
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0370(2) 0.67994(17) -0.13405(18) 0.0394(6) Uani 1 1 d . . .
H1 H 1.0028 0.5968 -0.1619 0.047 Uiso 1 1 calc R . .
N1 N 0.9181(3) 0.4192(2) -0.2379(2) 0.0348(6) Uani 1 1 d . . .
C1 C 0.7767(3) -0.0056(2) -0.3871(2) 0.0207(6) Uani 1 1 d . . .
O2 O 1.2457(2) 0.61849(19) -0.0260(2) 0.0523(6) Uani 1 1 d . . .
N2 N 0.7812(3) 0.4014(2) -0.5858(2) 0.0384(7) Uani 1 1 d . . .
C2 C 0.7815(3) -0.0752(3) -0.3005(2) 0.0270(7) Uani 1 1 d . . .
H2 H 0.8040 -0.0260 -0.2196 0.032 Uiso 1 1 calc R . .
C3 C 0.7550(3) -0.2147(3) -0.3257(3) 0.0301(7) Uani 1 1 d . . .
H3 H 0.7625 -0.2590 -0.2629 0.036 Uiso 1 1 calc R . .
C4 C 0.7186(3) -0.2852(3) -0.4416(3) 0.0291(7) Uani 1 1 d . . .
H4 H 0.7029 -0.3799 -0.4592 0.035 Uiso 1 1 calc R . .
C5 C 0.6568(3) -0.3013(3) -0.6581(3) 0.0306(7) Uani 1 1 d . . .
H5 H 0.6359 -0.3961 -0.6737 0.037 Uiso 1 1 calc R . .
C6 C 0.6420(3) -0.2431(3) -0.7518(3) 0.0338(7) Uani 1 1 d . . .
H6 H 0.6110 -0.2966 -0.8326 0.041 Uiso 1 1 calc R . .
C7 C 0.6729(3) -0.1037(3) -0.7276(2) 0.0274(7) Uani 1 1 d . . .
H7 H 0.6644 -0.0641 -0.7934 0.033 Uiso 1 1 calc R . .
C8 C 0.7152(3) -0.0211(2) -0.6133(2) 0.0221(6) Uani 1 1 d . . .
C9 C 0.7323(3) -0.0793(2) -0.5117(2) 0.0208(6) Uani 1 1 d . . .
C10 C 0.7029(3) -0.2220(2) -0.5377(2) 0.0238(6) Uani 1 1 d . . .
C11 C 0.8231(3) 0.1424(2) -0.3393(2) 0.0226(6) Uani 1 1 d . . .
C12 C 0.9565(3) 0.2162(2) -0.3393(2) 0.0255(7) Uani 1 1 d . . .
H12 H 1.0185 0.1733 -0.3738 0.031 Uiso 1 1 calc R . .
C13 C 0.9979(3) 0.3522(3) -0.2887(2) 0.0326(7) Uani 1 1 d . . .
H13 H 1.0891 0.4013 -0.2902 0.039 Uiso 1 1 calc R . .
C14 C 0.7910(3) 0.3477(3) -0.2359(3) 0.0355(8) Uani 1 1 d . . .
H14 H 0.7327 0.3930 -0.1989 0.043 Uiso 1 1 calc R . .
C15 C 0.7404(3) 0.2113(3) -0.2850(2) 0.0310(7) Uani 1 1 d . . .
H15 H 0.6492 0.1646 -0.2816 0.037 Uiso 1 1 calc R . .
C16 C 0.7378(3) 0.1250(3) -0.6040(2) 0.0234(6) Uani 1 1 d . . .
C17 C 0.8557(3) 0.1939(3) -0.6271(2) 0.0300(7) Uani 1 1 d . . .
H17 H 0.9238 0.1477 -0.6506 0.036 Uiso 1 1 calc R . .
C18 C 0.8740(3) 0.3297(3) -0.6158(2) 0.0352(7) Uani 1 1 d . . .
H18 H 0.9574 0.3750 -0.6301 0.042 Uiso 1 1 calc R . .
C19 C 0.6647(3) 0.3332(3) -0.5679(3) 0.0362(8) Uani 1 1 d . . .
H19 H 0.5952 0.3810 -0.5487 0.043 Uiso 1 1 calc R . .
C20 C 0.6384(3) 0.1977(3) -0.5756(2) 0.0274(7) Uani 1 1 d . . .
H20 H 0.5535 0.1547 -0.5615 0.033 Uiso 1 1 calc R . .
C21 C 1.1794(3) 0.7051(3) -0.0552(3) 0.0310(7) Uani 1 1 d . . .
C22 C 1.2534(3) 0.8480(3) -0.0040(3) 0.0326(7) Uani 1 1 d . . .
H22 H 1.3556 0.8719 0.0554 0.039 Uiso 1 1 calc R . .
C23 C 1.1877(3) 0.9454(3) -0.0349(2) 0.0281(7) Uani 1 1 d . . .
H23 H 1.0841 0.9190 -0.0919 0.034 Uiso 1 1 calc R . .
C24 C 1.2557(3) 1.0901(3) 0.0083(2) 0.0253(7) Uani 1 1 d . . .
C25 C 1.4106(3) 1.1431(3) 0.0819(2) 0.0333(7) Uani 1 1 d . . .
H25 H 1.4753 1.0848 0.1086 0.040 Uiso 1 1 calc R . .
C26 C 1.4713(3) 1.2796(3) 0.1165(3) 0.0377(8) Uani 1 1 d . . .
H26 H 1.5770 1.3145 0.1670 0.045 Uiso 1 1 calc R . .
C27 C 1.3787(4) 1.3656(3) 0.0779(3) 0.0379(8) Uani 1 1 d . . .
H27 H 1.4211 1.4592 0.1000 0.045 Uiso 1 1 calc R . .
C28 C 1.2248(3) 1.3151(3) 0.0073(2) 0.0335(7) Uani 1 1 d . . .
H28 H 1.1602 1.3742 -0.0173 0.040 Uiso 1 1 calc R . .
C29 C 1.1642(3) 1.1789(3) -0.0279(2) 0.0314(7) Uani 1 1 d . . .
H29 H 1.0581 1.1450 -0.0777 0.038 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N1 C14 116.9(2) . . ?
C2 C1 C9 118.9(2) . . ?
C2 C1 C11 114.8(2) . . ?
C9 C1 C11 126.3(2) . . ?
C19 N2 C18 115.9(2) . . ?
C1 C2 C3 123.2(3) . . ?
C4 C3 C2 118.5(3) . . ?
C3 C4 C10 122.0(3) . . ?
C6 C5 C10 120.6(3) . . ?
C5 C6 C7 119.1(3) . . ?
C8 C7 C6 123.2(3) . . ?
C7 C8 C9 119.2(2) . . ?
C7 C8 C16 116.4(2) . . ?
C9 C8 C16 124.4(2) . . ?
C10 C9 C1 117.7(2) . . ?
C10 C9 C8 116.9(2) . . ?
C1 C9 C8 125.4(2) . . ?
C5 C10 C4 119.4(2) . . ?
C5 C10 C9 121.0(2) . . ?
C4 C10 C9 119.6(2) . . ?
C12 C11 C15 117.2(2) . . ?
C12 C11 C1 121.5(2) . . ?
C15 C11 C1 121.2(2) . . ?
C13 C12 C11 119.2(3) . . ?
N1 C13 C12 124.0(3) . . ?
N1 C14 C15 123.1(3) . . ?
C14 C15 C11 119.7(3) . . ?
C17 C16 C20 117.0(2) . . ?
C17 C16 C8 121.5(2) . . ?
C20 C16 C8 121.5(2) . . ?
C18 C17 C16 119.7(3) . . ?
N2 C18 C17 123.9(3) . . ?
N2 C19 C20 124.4(3) . . ?
C19 C20 C16 119.1(3) . . ?
O2 C21 O1 123.6(3) . . ?
O2 C21 C22 122.1(3) . . ?
O1 C21 C22 114.3(3) . . ?
C23 C22 C21 124.4(3) . . ?
C22 C23 C24 127.7(3) . . ?
C25 C24 C29 117.9(2) . . ?
C25 C24 C23 122.6(3) . . ?
C29 C24 C23 119.4(2) . . ?
C26 C25 C24 120.8(3) . . ?
C27 C26 C25 120.2(3) . . ?
C28 C27 C26 119.7(3) . . ?
C27 C28 C29 120.1(3) . . ?
C28 C29 C24 121.2(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C21 1.313(3) . ?
N1 C13 1.329(3) . ?
N1 C14 1.337(3) . ?
C1 C2 1.378(3) . ?
C1 C9 1.440(3) . ?
C1 C11 1.486(3) . ?
O2 C21 1.215(3) . ?
N2 C19 1.335(3) . ?
N2 C18 1.338(3) . ?
C2 C3 1.397(3) . ?
C3 C4 1.353(4) . ?
C4 C10 1.418(3) . ?
C5 C6 1.362(4) . ?
C5 C10 1.414(3) . ?
C6 C7 1.396(3) . ?
C7 C8 1.373(3) . ?
C8 C9 1.443(3) . ?
C8 C16 1.487(3) . ?
C9 C10 1.428(3) . ?
C11 C12 1.387(3) . ?
C11 C15 1.385(3) . ?
C12 C13 1.375(3) . ?
C14 C15 1.378(3) . ?
C16 C17 1.384(3) . ?
C16 C20 1.389(3) . ?
C17 C18 1.379(3) . ?
C19 C20 1.381(3) . ?
C21 C22 1.467(4) . ?
C22 C23 1.317(3) . ?
C23 C24 1.469(3) . ?
C24 C25 1.393(3) . ?
C24 C29 1.393(3) . ?
C25 C26 1.382(4) . ?
C26 C27 1.381(4) . ?
C27 C28 1.375(4) . ?
C28 C29 1.379(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659282
