#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/18/4021849.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_4021849
loop_
_publ_author_name
'Yugang Chen'
'Mark G. Steinmetz'
_publ_contact_author_address
;Dept. of Chemistry
Marquette University
P.O. Box 1881
Milwaukee, WI 53201-1881
;
_publ_contact_author_email       mark.steinmetz@marquette.edu
_publ_contact_author_name        'Mark G. Steinmetz'
_publ_contact_author_phone       '414 288-3535'
_publ_section_title
;
 Photoactivation of Amino-Substituted 1,4-Benzoquinones for Release
 of Carboxylate and Phenolate Leaving Groups Using Visible Light
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6053
_journal_page_last               6060
_journal_paper_doi               10.1021/jo060790g
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C11 H11 Cl2 N O2'
_chemical_formula_weight         260.11
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 98.9320(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6303(6)
_cell_length_b                   7.5224(5)
_cell_length_c                   17.1285(12)
_cell_measurement_reflns_used    9572
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.5
_cell_measurement_theta_min      2.5
_cell_volume                     1098.51(13)
_computing_cell_refinement       'SAINT v7.23A (Bruker, 2005)'
_computing_data_collection       'APEX2 v1.0-27 (Bruker, 2005)'
_computing_data_reduction        'SADABS-2004/1 (Bruker, 2005)'
_computing_molecular_graphics    'XP v5.1 (Bruker, 1998)'
_computing_publication_material  'XCIF v6.12 (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'Bruker APEX2 CCD detector'
_diffrn_measurement_method       'omega scan'
_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  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0155
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            17715
_diffrn_reflns_theta_full        31.88
_diffrn_reflns_theta_max         31.88
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    0.573
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.835
_exptl_absorpt_correction_type   'semi-empirical (SADABS procedure)'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         3582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0528P)²+0.1249P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0811
_reflns_number_gt                3225
_reflns_number_total             3582
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo060790gsi20060602_105836.cif
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4021849
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
Cl1 Cl 0.18214(3) 0.40748(4) 0.097734(13) 0.03103(8) Uani 1 1 d
Cl2 Cl 0.48804(3) 0.37364(3) 0.392277(15) 0.03102(8) Uani 1 1 d
O1 O 0.42797(7) 0.33570(9) 0.22394(4) 0.02524(14) Uani 1 1 d
O2 O -0.08907(7) 0.49986(9) 0.34106(4) 0.02195(13) Uani 1 1 d
C1 C 0.30648(10) 0.37802(11) 0.24842(5) 0.01874(15) Uani 1 1 d
C2 C 0.16018(10) 0.40909(11) 0.19673(5) 0.01896(15) Uani 1 1 d
C3 C 0.02093(9) 0.45270(10) 0.22327(5) 0.01598(14) Uani 1 1 d
C4 C 0.02925(9) 0.47448(10) 0.31216(5) 0.01642(14) Uani 1 1 d
C5 C 0.18131(10) 0.45538(11) 0.36584(5) 0.01872(15) Uani 1 1 d
C6 C 0.30787(10) 0.40562(11) 0.33476(5) 0.01937(16) Uani 1 1 d
C7 C 0.17721(12) 0.48774(15) 0.45153(5) 0.02672(18) Uani 1 1 d
N1 N -0.12121(8) 0.46812(9) 0.17891(4) 0.01753(13) Uani 1 1 d
C8 C -0.16483(11) 0.38844(13) 0.09950(5) 0.02477(18) Uani 1 1 d
C9 C -0.34199(11) 0.41210(12) 0.08205(6) 0.02440(18) Uani 1 1 d
C10 C -0.36511(10) 0.58882(12) 0.12189(6) 0.02341(17) Uani 1 1 d
C11 C -0.25581(9) 0.57161(11) 0.20061(5) 0.01971(16) Uani 1 1 d
H7A H 0.1304(19) 0.603(2) 0.4579(9) 0.041(4) Uiso 1 1 d
H7B H 0.278(2) 0.484(3) 0.4775(11) 0.062(5) Uiso 1 1 d
H7C H 0.1122(19) 0.397(2) 0.4718(9) 0.046(4) Uiso 1 1 d
H8A H -0.1288(16) 0.263(2) 0.1015(8) 0.034(3) Uiso 1 1 d
H8B H -0.1155(17) 0.4560(18) 0.0615(8) 0.034(3) Uiso 1 1 d
H9A H -0.3772(18) 0.409(2) 0.0246(9) 0.038(4) Uiso 1 1 d
H9B H -0.3932(15) 0.3188(17) 0.1048(8) 0.029(3) Uiso 1 1 d
H10A H -0.3365(15) 0.6837(19) 0.0909(8) 0.033(3) Uiso 1 1 d
H10B H -0.4745(15) 0.6091(16) 0.1311(8) 0.024(3) Uiso 1 1 d
H11A H -0.2170(14) 0.6820(17) 0.2226(7) 0.022(3) Uiso 1 1 d
H11B H -0.3074(15) 0.5060(18) 0.2384(8) 0.027(3) Uiso 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'
O O 0.0106 0.0060 '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_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 C2 122.90(8)
O1 C1 C6 119.86(8)
C2 C1 C6 117.20(7)
C3 C2 C1 123.79(8)
C3 C2 Cl1 123.57(6)
C1 C2 Cl1 112.35(6)
N1 C3 C2 126.55(7)
N1 C3 C4 116.97(7)
C2 C3 C4 116.37(7)
O2 C4 C5 118.63(7)
O2 C4 C3 120.76(7)
C5 C4 C3 120.53(7)
C6 C5 C4 118.46(7)
C6 C5 C7 125.51(8)
C4 C5 C7 115.99(7)
C5 C6 C1 123.43(7)
C5 C6 Cl2 122.03(7)
C1 C6 Cl2 114.52(6)
C3 N1 C8 124.34(7)
C3 N1 C11 125.56(7)
C8 N1 C11 110.08(6)
N1 C8 C9 103.73(7)
C10 C9 C8 102.23(7)
C9 C10 C11 102.47(7)
N1 C11 C10 102.85(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C2 1.7352(9)
Cl2 C6 1.7235(8)
O1 C1 1.2301(10)
O2 C4 1.2169(10)
C1 C2 1.4442(12)
C1 C6 1.4916(12)
C2 C3 1.3886(11)
C3 N1 1.3440(10)
C3 C4 1.5219(11)
C4 C5 1.4878(11)
C5 C6 1.3405(12)
C5 C7 1.4937(12)
N1 C8 1.4804(11)
N1 C11 1.4925(10)
C8 C9 1.5221(13)
C9 C10 1.5215(13)
C10 C11 1.5263(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10024806
