#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/28/4022819.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_4022819
loop_
_publ_author_name
'Cédric Brulé'
'Kenneth K. Laali'
'Takao Okazaki'
'Mahesh K. Lakshman'
_publ_contact_author_address
;Department of Chemistry
Kent State University
Kent, OH 44242, USA
;
_publ_contact_author_email       klaali@kent.edu
_publ_contact_author_fax         330-672-3816
_publ_contact_author_name        'Kenneth K. Laali'
_publ_contact_author_phone       330-672-2988
_publ_section_title
;
 Structure/Reactivity Relationships in the Benzo[c]phenanthrene
 Skeleton: Stable Ion and Electrophilic Substitution (Nitration,
 Bromination) Study of Substituted Analogues, Novel Carbocations
 and Substituted Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3232
_journal_page_last               3241
_journal_paper_doi               10.1021/jo0625453
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C20 H15 N O4'
_chemical_formula_weight         333.33
_chemical_name_common
'3,4-dimethoxy-1-nitrobenzo[c]phenanthrene (7aNO2)'
_chemical_name_systematic
;

 3,4-dimethoxy-1-nitrobenzo[c]phenanthrene

;
_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                 97.034(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.244(3)
_cell_length_b                   4.5021(14)
_cell_length_c                   33.041(9)
_cell_measurement_reflns_used    1119
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      29.62
_cell_measurement_theta_min      2.90
_cell_volume                     1512.3(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.883
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0504
_diffrn_reflns_av_sigmaI/netI    0.0618
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            3806
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         1.24
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_correction_T_min  0.9797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       irregular
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.771
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         2392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.771
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0398
_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)+(0.1000P)²+0.8835P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1324
_reflns_number_gt                1730
_reflns_number_total             2392
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0625453si20070228_015723.cif
_cod_data_source_block           laali013_01
_cod_depositor_comments
;
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.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed
to 'multi-scan' 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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4022819
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
N1 N 0.47512(19) 0.0449(4) 0.06771(6) 0.0168(5) Uani 1 1 d
O1 O 0.43114(16) 0.2719(4) 0.08134(5) 0.0210(4) Uani 1 1 d
O2 O 0.41293(16) -0.1082(4) 0.04124(5) 0.0225(5) Uani 1 1 d
O3 O 0.88324(16) -0.3407(4) 0.03266(5) 0.0214(5) Uani 1 1 d
O4 O 1.01462(15) -0.0958(4) 0.10010(5) 0.0210(5) Uani 1 1 d
C1 C 0.8118(2) -0.2082(5) 0.05962(8) 0.0177(6) Uani 1 1 d
C2 C 0.8794(2) -0.0805(5) 0.09385(8) 0.0182(6) Uani 1 1 d
C3 C 0.8135(2) 0.0558(5) 0.12359(8) 0.0171(6) Uani 1 1 d
C4 C 0.8870(2) 0.2119(6) 0.15656(8) 0.0204(6) Uani 1 1 d
C5 C 0.8255(2) 0.3534(5) 0.18440(8) 0.0207(6) Uani 1 1 d
C6 C 0.6871(2) 0.3128(5) 0.18595(8) 0.0178(6) Uani 1 1 d
C7 C 0.6284(3) 0.4318(5) 0.21914(8) 0.0216(6) Uani 1 1 d
C8 C 0.5030(3) 0.3676(5) 0.22442(9) 0.0199(6) Uani 1 1 d
C9 C 0.4288(2) 0.1633(5) 0.19830(8) 0.0175(6) Uani 1 1 d
C10 C 0.3020(3) 0.0725(6) 0.20599(9) 0.0209(6) Uani 1 1 d
C11 C 0.2333(3) -0.1377(6) 0.18239(9) 0.0226(7) Uani 1 1 d
C12 C 0.2912(2) -0.2734(6) 0.15109(8) 0.0197(6) Uani 1 1 d
C13 C 0.4129(2) -0.1871(5) 0.14280(8) 0.0171(6) Uani 1 1 d
C14 C 0.4838(2) 0.0420(5) 0.16467(8) 0.0162(6) Uani 1 1 d
C15 C 0.6121(2) 0.1401(5) 0.15616(8) 0.0172(6) Uani 1 1 d
C16 C 0.6735(2) 0.0529(5) 0.12078(7) 0.0159(6) Uani 1 1 d
C17 C 0.6111(2) -0.0403(5) 0.08231(8) 0.0165(6) Uani 1 1 d
C18 C 0.6758(2) -0.1741(5) 0.05330(8) 0.0179(6) Uani 1 1 d
C19 C 0.8111(3) -0.5119(6) 0.00071(9) 0.0215(6) Uani 1 1 d
C20 C 1.0792(3) 0.1067(6) 0.07517(9) 0.0234(7) Uani 1 1 d
H1 H 0.872(2) 0.478(6) 0.2055(8) 0.024(7) Uiso 1 1 d
H2 H 0.270(2) 0.165(5) 0.2291(8) 0.016(7) Uiso 1 1 d
H3 H 0.467(3) 0.446(6) 0.2472(9) 0.027(8) Uiso 1 1 d
H4 H 0.681(3) 0.560(6) 0.2388(9) 0.032(8) Uiso 1 1 d
H5 H 0.250(3) -0.436(6) 0.1368(8) 0.024(7) Uiso 1 1 d
H6 H 0.455(2) -0.282(6) 0.1229(8) 0.013(6) Uiso 1 1 d
H7 H 0.144(2) -0.197(5) 0.1874(7) 0.013(6) Uiso 1 1 d
H8 H 0.628(2) -0.230(6) 0.0293(8) 0.021(7) Uiso 1 1 d
H9 H 0.982(3) 0.220(6) 0.1571(8) 0.022(7) Uiso 1 1 d
H10 H 0.754(2) -0.668(6) 0.0133(8) 0.020(7) Uiso 1 1 d
H11 H 0.756(3) -0.386(6) -0.0195(8) 0.020(7) Uiso 1 1 d
H12 H 0.880(3) -0.608(6) -0.0124(9) 0.026(8) Uiso 1 1 d
H13 H 1.055(3) 0.315(7) 0.0829(9) 0.038(8) Uiso 1 1 d
H14 H 1.175(3) 0.061(6) 0.0826(8) 0.020(7) Uiso 1 1 d
H15 H 1.050(2) 0.073(5) 0.0465(8) 0.017(6) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 N1 O2 123.21(19)
O1 N1 C17 118.30(18)
O2 N1 C17 118.41(19)
C1 O3 C19 116.58(19)
C2 O4 C20 113.97(19)
O3 C1 C2 117.6(2)
O3 C1 C18 124.1(2)
C2 C1 C18 118.1(2)
O4 C2 C1 119.9(2)
O4 C2 C3 118.7(2)
C1 C2 C3 121.4(2)
C2 C3 C16 121.2(2)
C2 C3 C4 119.7(2)
C16 C3 C4 119.0(2)
C5 C4 C3 120.6(2)
C5 C4 H9 121.5(16)
C3 C4 H9 117.8(16)
C4 C5 C6 120.9(2)
C4 C5 H1 122.3(15)
C6 C5 H1 116.7(15)
C15 C6 C7 120.2(2)
C15 C6 C5 120.1(2)
C7 C6 C5 119.5(2)
C8 C7 C6 121.3(2)
C8 C7 H4 119.4(17)
C6 C7 H4 119.3(17)
C7 C8 C9 120.6(3)
C7 C8 H3 119.4(17)
C9 C8 H3 119.8(17)
C10 C9 C14 119.5(2)
C10 C9 C8 121.0(3)
C14 C9 C8 119.5(2)
C11 C10 C9 121.2(3)
C11 C10 H2 123.4(15)
C9 C10 H2 115.4(15)
C10 C11 C12 119.4(3)
C10 C11 H7 121.1(15)
C12 C11 H7 119.4(15)
C13 C12 C11 120.4(2)
C13 C12 H5 118.9(17)
C11 C12 H5 120.5(17)
C12 C13 C14 122.1(3)
C12 C13 H6 121.7(15)
C14 C13 H6 116.2(15)
C13 C14 C9 117.1(2)
C13 C14 C15 123.2(2)
C9 C14 C15 119.6(2)
C6 C15 C14 117.6(2)
C6 C15 C16 117.5(2)
C14 C15 C16 124.7(2)
C17 C16 C3 113.7(2)
C17 C16 C15 127.8(2)
C3 C16 C15 118.6(2)
C18 C17 C16 123.7(2)
C18 C17 N1 113.9(2)
C16 C17 N1 121.6(2)
C17 C18 C1 120.3(2)
C17 C18 H8 118.4(16)
C1 C18 H8 121.2(16)
O3 C19 H10 109.5(15)
O3 C19 H11 112.6(15)
H10 C19 H11 111(2)
O3 C19 H12 103.3(16)
H10 C19 H12 111(2)
H11 C19 H12 110(2)
O4 C20 H13 107.3(17)
O4 C20 H14 103.4(15)
H13 C20 H14 113(2)
O4 C20 H15 110.5(15)
H13 C20 H15 110(2)
H14 C20 H15 113(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 O1 1.225(3)
N1 O2 1.229(2)
N1 C17 1.468(3)
O3 C1 1.358(3)
O3 C19 1.437(3)
O4 C2 1.376(3)
O4 C20 1.442(3)
C1 C2 1.378(3)
C1 C18 1.391(3)
C2 C3 1.400(4)
C3 C16 1.426(3)
C3 C4 1.431(3)
C4 C5 1.338(4)
C4 H9 0.97(3)
C5 C6 1.436(4)
C5 H1 0.97(3)
C6 C15 1.407(3)
C6 C7 1.419(4)
C7 C8 1.349(4)
C7 H4 0.98(3)
C8 C9 1.417(3)
C8 H3 0.94(3)
C9 C10 1.414(4)
C9 C14 1.416(4)
C10 C11 1.365(4)
C10 H2 0.96(3)
C11 C12 1.395(4)
C11 H7 0.98(2)
C12 C13 1.365(4)
C12 H5 0.94(3)
C13 C14 1.409(3)
C13 H6 0.93(3)
C14 C15 1.446(4)
C15 C16 1.448(4)
C16 C17 1.415(3)
C17 C18 1.370(4)
C18 H8 0.92(3)
C19 H10 1.03(3)
C19 H11 1.00(3)
C19 H12 0.97(3)
C20 H13 1.01(3)
C20 H14 1.00(3)
C20 H15 0.97(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17342713
