#------------------------------------------------------------------------------
#$Date: 2017-01-08 20:07:17 +0200 (Sun, 08 Jan 2017) $
#$Revision: 190051 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/93/7119375.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_7119375
loop_
_publ_author_name
Chun-Wei
Kuo
Ashok
Konala
Lyu
Lin
Ting-Ta
Chiang
Chia-Yu
Huang
Tang-Hao
Yang
Veerababurao
Kavala
Ching-Fa
Yao
_publ_section_title
;
 Synthesis of benzo[a]carbazole derivatives from 3-ethylindoles by
 exploiting the dual character of benzoquinone as an oxidizing agent and
 dienophile
;
_journal_name_full               Chem.Commun.
_journal_page_first              7870
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C20 H15 N O3'
_chemical_formula_sum            'C20 H15 N O3'
_chemical_formula_weight         317.33
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-03-03 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5517(18)
_cell_length_b                   11.006(4)
_cell_length_c                   24.121(8)
_cell_measurement_reflns_used    1622
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.08
_cell_measurement_theta_min      2.50
_cell_volume                     1473.8(9)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX2'
_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  0.0740
_diffrn_reflns_av_sigmaI/netI    0.0837
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9139
_diffrn_reflns_theta_full        25.14
_diffrn_reflns_theta_max         25.14
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9981
_exptl_absorpt_correction_T_min  0.9433
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.61
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -1(2)
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2609
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0484
_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)+(0.0609P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1252
_reflns_number_gt                1853
_reflns_number_total             2609
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc03124b2.cif
_cod_data_source_block           ch17812
_cod_original_cell_volume        1473.8(8)
_cod_database_code               7119375
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
C1 C 0.2392(6) 0.1513(3) 0.19351(15) 0.0299(9) Uani 1 1 d . . .
C2 C 0.1086(6) 0.2338(3) 0.15652(15) 0.0340(9) Uani 1 1 d . . .
H2 H -0.0289 0.2756 0.1701 0.041 Uiso 1 1 calc R . .
C3 C 0.1776(6) 0.2516(3) 0.10440(15) 0.0310(9) Uani 1 1 d . . .
H3 H 0.0848 0.3040 0.0815 0.037 Uiso 1 1 calc R . .
C4 C 0.3931(6) 0.1929(3) 0.08088(14) 0.0248(8) Uani 1 1 d . . .
C5 C 0.5238(6) 0.1059(3) 0.11609(13) 0.0236(8) Uani 1 1 d . . .
C6 C 0.4480(6) 0.0833(3) 0.17077(14) 0.0270(8) Uani 1 1 d . . .
C7 C 0.5658(6) -0.0036(3) 0.20391(14) 0.0263(8) Uani 1 1 d . . .
C8 C 0.5025(7) -0.0261(3) 0.26350(15) 0.0352(9) Uani 1 1 d . . .
C9 C 0.6178(7) 0.0593(4) 0.30372(14) 0.0525(12) Uani 1 1 d . . .
H9A H 0.5674 0.0384 0.3415 0.079 Uiso 1 1 calc R . .
H9B H 0.5681 0.1427 0.2952 0.079 Uiso 1 1 calc R . .
H9C H 0.7934 0.0528 0.3008 0.079 Uiso 1 1 calc R . .
C10 C 0.7595(6) -0.0687(3) 0.18280(13) 0.0277(9) Uani 1 1 d . . .
H10 H 0.8369 -0.1284 0.2050 0.033 Uiso 1 1 calc R . .
C11 C 0.8392(6) -0.0466(3) 0.12967(12) 0.0223(8) Uani 1 1 d . . .
C12 C 0.7239(6) 0.0415(3) 0.09614(12) 0.0226(8) Uani 1 1 d . . .
C13 C 1.0309(5) -0.0352(3) 0.04581(13) 0.0221(8) Uani 1 1 d . . .
C14 C 1.0341(6) -0.0951(3) 0.09701(13) 0.0231(8) Uani 1 1 d . . .
C15 C 1.2130(6) -0.1810(3) 0.10851(14) 0.0278(9) Uani 1 1 d . . .
H15 H 1.2199 -0.2210 0.1434 0.033 Uiso 1 1 calc R . .
C16 C 1.3780(6) -0.2056(3) 0.06771(14) 0.0290(9) Uani 1 1 d . . .
H16 H 1.5006 -0.2640 0.0744 0.035 Uiso 1 1 calc R . .
C17 C 1.3692(6) -0.1460(3) 0.01643(14) 0.0268(8) Uani 1 1 d . . .
H17 H 1.4854 -0.1664 -0.0109 0.032 Uiso 1 1 calc R . .
C18 C 1.1981(6) -0.0587(3) 0.00395(13) 0.0234(8) Uani 1 1 d . . .
C19 C 1.1882(6) 0.0083(3) -0.05071(12) 0.0280(8) Uani 1 1 d . . .
H19A H 1.0234 0.0003 -0.0660 0.034 Uiso 1 1 calc R . .
H19B H 1.2165 0.0957 -0.0434 0.034 Uiso 1 1 calc R . .
C20 C 1.3644(6) -0.0331(3) -0.09422(14) 0.0341(9) Uani 1 1 d . . .
N1 N 0.8376(4) 0.0477(2) 0.04575(10) 0.0221(6) Uani 1 1 d . . .
H1' H 0.8290 0.1178 0.0221 0.026 Uiso 1 1 d R . .
O1 O 0.1746(5) 0.1384(2) 0.24152(10) 0.0447(7) Uani 1 1 d . . .
O2 O 0.4602(4) 0.2171(2) 0.03364(9) 0.0303(6) Uani 1 1 d . . .
O3 O 0.3889(6) -0.1150(3) 0.27741(11) 0.0589(9) Uani 1 1 d . . .
H20A H 1.3494 -0.1212 -0.1078 0.071 Uiso 1 1 d R . .
H20B H 1.3740 0.0074 -0.1287 0.071 Uiso 1 1 d R . .
H20C H 1.5169 -0.0425 -0.0831 0.071 Uiso 1 1 d 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
O1 C1 C2 120.3(3) . .
O1 C1 C6 121.4(3) . .
C2 C1 C6 118.3(3) . .
C3 C2 C1 121.7(3) . .
C3 C2 H2 119.2 . .
C1 C2 H2 119.2 . .
C2 C3 C4 122.3(3) . .
C2 C3 H3 118.9 . .
C4 C3 H3 118.9 . .
O2 C4 C5 121.8(3) . .
O2 C4 C3 120.6(3) . .
C5 C4 C3 117.6(3) . .
C12 C5 C6 118.0(3) . .
C12 C5 C4 121.4(3) . .
C6 C5 C4 120.6(3) . .
C5 C6 C7 120.9(3) . .
C5 C6 C1 119.4(3) . .
C7 C6 C1 119.7(3) . .
C10 C7 C6 120.1(3) . .
C10 C7 C8 116.6(3) . .
C6 C7 C8 123.2(3) . .
O3 C8 C9 123.4(4) . .
O3 C8 C7 121.4(3) . .
C9 C8 C7 114.7(3) . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C11 C10 C7 119.9(3) . .
C11 C10 H10 120.1 . .
C7 C10 H10 120.1 . .
C10 C11 C12 120.5(3) . .
C10 C11 C14 133.2(3) . .
C12 C11 C14 106.3(3) . .
N1 C12 C5 130.1(3) . .
N1 C12 C11 109.4(3) . .
C5 C12 C11 120.5(3) . .
C18 C13 C14 122.8(3) . .
C18 C13 N1 128.8(3) . .
C14 C13 N1 108.4(3) . .
C15 C14 C13 120.1(3) . .
C15 C14 C11 132.5(3) . .
C13 C14 C11 107.4(3) . .
C16 C15 C14 117.7(3) . .
C16 C15 H15 121.1 . .
C14 C15 H15 121.1 . .
C15 C16 C17 121.2(3) . .
C15 C16 H16 119.4 . .
C17 C16 H16 119.4 . .
C18 C17 C16 122.7(3) . .
C18 C17 H17 118.6 . .
C16 C17 H17 118.6 . .
C17 C18 C13 115.4(3) . .
C17 C18 C19 123.6(3) . .
C13 C18 C19 121.0(3) . .
C20 C19 C18 115.9(3) . .
C20 C19 H19A 108.3 . .
C18 C19 H19A 108.3 . .
C20 C19 H19B 108.3 . .
C18 C19 H19B 108.3 . .
H19A C19 H19B 107.4 . .
C19 C20 H20A 117.1 . .
C19 C20 H20B 120.5 . .
H20A C20 H20B 99.7 . .
C19 C20 H20C 116.2 . .
H20A C20 H20C 93.6 . .
H20B C20 H20C 105.4 . .
C12 N1 C13 108.5(2) . .
C12 N1 H1' 122.9 . .
C13 N1 H1' 124.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.220(4) .
C1 C2 1.465(4) .
C1 C6 1.485(5) .
C2 C3 1.329(5) .
C2 H2 0.9500 .
C3 C4 1.473(5) .
C3 H3 0.9500 .
C4 O2 1.228(4) .
C4 C5 1.472(4) .
C5 C12 1.403(4) .
C5 C6 1.407(4) .
C6 C7 1.408(5) .
C7 C10 1.389(5) .
C7 C8 1.500(5) .
C8 O3 1.211(4) .
C8 C9 1.495(5) .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 C11 1.378(4) .
C10 H10 0.9500 .
C11 C12 1.416(4) .
C11 C14 1.441(4) .
C12 N1 1.371(4) .
C13 C18 1.396(4) .
C13 C14 1.400(4) .
C13 N1 1.408(4) .
C14 C15 1.400(5) .
C15 C16 1.371(4) .
C15 H15 0.9500 .
C16 C17 1.401(4) .
C16 H16 0.9500 .
C17 C18 1.384(5) .
C17 H17 0.9500 .
C18 C19 1.512(4) .
C19 C20 1.505(4) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 H20A 1.0272 .
C20 H20B 0.9454 .
C20 H20C 0.8941 .
N1 H1' 0.9605 .
