#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:36:15 +0100 (lun 21 de mar de 2016) $
#$Revision: 178474 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/95/4029507.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_4029507
loop_
_publ_author_name
'Parent, Alexander A.'
'Ess, Daniel H.'
'Katzenellenbogen, John A.'
_publ_contact_author
; 
Danielle L. Gray 
University of Illinois 
School of Chemical Sciences, Box 59-1 
505 South Mathews Avenue 
Urbana, Illinois  61801 
USA 
;
_publ_section_title
;
 π-π Interaction Energies as Determinants of the Photodimerization of
 Mono-, Di-, and Triazastilbenes.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5448
_journal_page_last               5462
_journal_paper_doi               10.1021/jo500457n
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C12 H8 Cl2 N2'
_chemical_formula_sum            'C12 H8 Cl2 N2'
_chemical_formula_weight         251.10
_chemical_name_systematic
; 
? 
;
_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
_audit_update_record
; 
? 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.686(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.6016(11)
_cell_length_b                   5.1312(4)
_cell_length_c                   16.3770(12)
_cell_measurement_reflns_used    1380
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      22.93
_cell_measurement_theta_min      3.75
_cell_volume                     1139.17(15)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 V2.0-1 (Bruker, 2004)'
_computing_data_reduction
; 
SAINT V7.23A, XPREP V2005/2, SADABS V2007/4, TWINABS V2007/5 
(Bruker, 2005 & 2007) 
;
_computing_molecular_graphics
; 
SHELXTL V6.12 (Bruker, 2005), CrystalMaker v2.1.3 (CrystalMaker, 1994) 
;
_computing_publication_material  'XCIF V6.12 (Bruker, 2005)'
_computing_structure_refinement  'SHELXTL V6.12 (Bruker, 2005)'
_computing_structure_solution    'SHELXTL V6.12 (Bruker, 2005)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Kappa/ApexII CCD'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  ba24eas
_diffrn_reflns_av_R_equivalents  0.0833
_diffrn_reflns_av_sigmaI/netI    0.0546
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14830
_diffrn_reflns_theta_full        25.42
_diffrn_reflns_theta_max         25.42
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.540
_exptl_absorpt_correction_T_max  0.9923
_exptl_absorpt_correction_T_min  0.9306
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL/XPREP V2005/2 (Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_exptl_crystal_id                ba24eas
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (-1 0 1) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0375
_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)+(0.0327P)²+0.0419P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0810
_reflns_number_gt                1440
_reflns_number_total             2113
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo500457n_si_001.cif
_cod_data_source_block           ba24eas
_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/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 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4029504--4029507.cif.
;
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               4029507
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
Cl2 Cl 0.72540(5) 0.05791(12) 0.18555(4) 0.03370(19) Uani 1 1 d .
Cl1 Cl 0.77297(5) 0.76348(14) -0.03528(4) 0.0415(2) Uani 1 1 d .
N2 N 0.73786(14) 0.4203(4) 0.07514(12) 0.0291(5) Uani 1 1 d .
N1 N 0.61061(15) 0.7286(4) 0.03692(11) 0.0262(5) Uani 1 1 d .
C12 C 0.58485(18) 0.4061(5) 0.13721(14) 0.0260(6) Uani 1 1 d .
H12A H 0.5450 0.3242 0.1729 0.031 Uiso 1 1 calc R
C10 C 0.69793(18) 0.6199(5) 0.03286(14) 0.0277(6) Uani 1 1 d .
C6 C 0.42155(18) 0.6158(5) 0.24079(15) 0.0308(6) Uani 1 1 d .
C8 C 0.45771(17) 0.7544(5) 0.09808(14) 0.0305(6) Uani 1 1 d .
H8A H 0.4347 0.8545 0.0532 0.037 Uiso 1 1 calc R
C11 C 0.67793(19) 0.3176(4) 0.12646(14) 0.0253(6) Uani 1 1 d .
C7 C 0.40044(18) 0.7463(5) 0.16023(15) 0.0342(6) Uani 1 1 d .
H7A H 0.3402 0.8323 0.1523 0.041 Uiso 1 1 calc R
C5 C 0.50036(19) 0.6907(5) 0.29418(16) 0.0382(7) Uani 1 1 d .
H5A H 0.5403 0.8278 0.2800 0.046 Uiso 1 1 calc R
C1 C 0.36136(19) 0.4124(5) 0.26359(16) 0.0356(7) Uani 1 1 d .
H1A H 0.3069 0.3623 0.2291 0.043 Uiso 1 1 calc R
C9 C 0.55288(18) 0.6241(4) 0.09213(14) 0.0245(6) Uani 1 1 d .
C4 C 0.5209(2) 0.5656(6) 0.36835(16) 0.0448(7) Uani 1 1 d .
H4A H 0.5739 0.6193 0.4039 0.054 Uiso 1 1 calc R
C2 C 0.3828(2) 0.2852(6) 0.33755(17) 0.0446(8) Uani 1 1 d .
H2A H 0.3432 0.1481 0.3523 0.053 Uiso 1 1 calc R
C3 C 0.4626(2) 0.3611(6) 0.38938(17) 0.0442(8) Uani 1 1 d .
H3A H 0.4770 0.2739 0.4387 0.053 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
Cl2 0.0405(4) 0.0250(3) 0.0339(4) 0.0016(3) -0.0070(3) 0.0052(3)
Cl1 0.0442(4) 0.0451(4) 0.0374(4) 0.0047(4) 0.0162(3) -0.0016(3)
N2 0.0312(12) 0.0274(12) 0.0284(12) -0.0020(10) 0.0013(10) 0.0021(10)
N1 0.0295(12) 0.0261(12) 0.0231(11) 0.0014(10) 0.0023(9) -0.0018(10)
C12 0.0300(15) 0.0256(15) 0.0224(13) -0.0010(11) 0.0027(11) -0.0018(12)
C10 0.0303(15) 0.0304(15) 0.0228(13) -0.0058(11) 0.0049(11) -0.0046(12)
C6 0.0259(15) 0.0352(16) 0.0325(15) -0.0001(12) 0.0106(12) 0.0081(12)
C8 0.0297(15) 0.0286(14) 0.0323(15) 0.0046(12) -0.0020(12) 0.0002(13)
C11 0.0339(15) 0.0175(13) 0.0234(13) -0.0040(10) -0.0040(11) -0.0012(11)
C7 0.0271(15) 0.0334(16) 0.0426(16) 0.0026(14) 0.0064(12) 0.0053(13)
C5 0.0348(17) 0.0442(18) 0.0364(16) -0.0014(14) 0.0083(13) -0.0036(13)
C1 0.0287(15) 0.0373(16) 0.0413(16) -0.0002(14) 0.0060(12) 0.0011(13)
C9 0.0280(14) 0.0204(14) 0.0241(13) -0.0015(10) -0.0035(11) -0.0017(11)
C4 0.0403(18) 0.063(2) 0.0314(16) -0.0075(16) 0.0030(13) 0.0008(16)
C2 0.0429(19) 0.0439(19) 0.0489(18) 0.0129(16) 0.0157(15) 0.0027(15)
C3 0.048(2) 0.055(2) 0.0305(16) 0.0066(14) 0.0093(14) 0.0129(16)
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 0.00 1.00 0.0100
1.00 0.00 -1.00 0.0200
0.00 1.00 0.00 0.1100
0.00 -1.00 0.00 0.1200
0.00 0.00 1.00 0.0100
0.00 0.00 -1.00 0.0100
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C11 N2 C10 113.0(2)
C10 N1 C9 116.1(2)
C11 C12 C9 116.8(2)
C11 C12 H12A 121.6
C9 C12 H12A 121.6
N1 C10 N2 129.2(2)
N1 C10 Cl1 115.60(19)
N2 C10 Cl1 115.19(19)
C5 C6 C1 118.7(2)
C5 C6 C7 121.3(2)
C1 C6 C7 119.9(2)
C7 C8 C9 127.6(2)
C7 C8 H8A 116.2
C9 C8 H8A 116.2
N2 C11 C12 124.9(2)
N2 C11 Cl2 115.93(19)
C12 C11 Cl2 119.15(19)
C8 C7 C6 127.6(2)
C8 C7 H7A 116.2
C6 C7 H7A 116.2
C6 C5 C4 121.2(3)
C6 C5 H5A 119.4
C4 C5 H5A 119.4
C2 C1 C6 120.0(3)
C2 C1 H1A 120.0
C6 C1 H1A 120.0
N1 C9 C12 120.0(2)
N1 C9 C8 115.2(2)
C12 C9 C8 124.8(2)
C3 C4 C5 119.6(3)
C3 C4 H4A 120.2
C5 C4 H4A 120.2
C3 C2 C1 120.3(3)
C3 C2 H2A 119.9
C1 C2 H2A 119.9
C4 C3 C2 120.2(3)
C4 C3 H3A 119.9
C2 C3 H3A 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl2 C11 1.740(2)
Cl1 C10 1.737(2)
N2 C11 1.327(3)
N2 C10 1.327(3)
N1 C10 1.319(3)
N1 C9 1.356(3)
C12 C11 1.370(3)
C12 C9 1.390(3)
C12 H12A 0.9300
C6 C5 1.381(4)
C6 C1 1.396(3)
C6 C7 1.487(3)
C8 C7 1.332(3)
C8 C9 1.467(3)
C8 H8A 0.9300
C7 H7A 0.9300
C5 C4 1.382(4)
C5 H5A 0.9300
C1 C2 1.386(4)
C1 H1A 0.9300
C4 C3 1.376(4)
C4 H4A 0.9300
C2 C3 1.378(4)
C2 H2A 0.9300
C3 H3A 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
C9 N1 C10 N2 0.3(4)
C9 N1 C10 Cl1 -177.63(16)
C11 N2 C10 N1 1.9(4)
C11 N2 C10 Cl1 179.84(17)
C10 N2 C11 C12 -1.0(3)
C10 N2 C11 Cl2 -179.00(16)
C9 C12 C11 N2 -1.8(4)
C9 C12 C11 Cl2 176.12(17)
C9 C8 C7 C6 3.9(4)
C5 C6 C7 C8 62.4(4)
C1 C6 C7 C8 -117.4(3)
C1 C6 C5 C4 1.0(4)
C7 C6 C5 C4 -178.7(2)
C5 C6 C1 C2 -1.8(4)
C7 C6 C1 C2 178.0(2)
C10 N1 C9 C12 -3.4(3)
C10 N1 C9 C8 177.6(2)
C11 C12 C9 N1 4.1(3)
C11 C12 C9 C8 -177.0(2)
C7 C8 C9 N1 -159.0(2)
C7 C8 C9 C12 22.1(4)
C6 C5 C4 C3 0.6(4)
C6 C1 C2 C3 0.9(4)
C5 C4 C3 C2 -1.4(4)
C1 C2 C3 C4 0.7(4)
