#------------------------------------------------------------------------------
#$Date: 2016-03-05 07:52:51 +0100 (Sat 05 de Mar de 2016) $
#$Revision: 177632 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/83/7118383.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_7118383
loop_
_publ_author_name
'Sadhu, Pradeep'
'Punniyamurthy, Tharmalingam'
_publ_section_title
;
 Copper(ii)-mediated regioselective N-arylation of pyrroles, indoles,
 pyrazoles and carbazole via dehydrogenative coupling.
;
_journal_issue                   13
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2803
_journal_page_last               2806
_journal_paper_doi               10.1039/c5cc08206d
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C20 H15 N3 O'
_chemical_formula_sum            'C20 H15 N3 O'
_chemical_formula_weight         313.35
_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
;
2015-09-24 deposited with the CCDC.
2016-01-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.513(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7059(3)
_cell_length_b                   15.7541(4)
_cell_length_c                   10.5250(3)
_cell_measurement_temperature    296(2)
_cell_volume                     1601.91(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      296(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_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  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0159
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            21958
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2701
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0405
_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)+(0.0557P)²+0.2191P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1011
_reflns_number_gt                2317
_reflns_number_total             2701
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5cc08206d2.cif
_cod_data_source_block           sp_1
_cod_depositor_comments          'Adding full bibliography for 7118383.cif.'
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7118383
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
C11 C 0.56692(14) 0.11376(8) 0.30234(12) 0.0427(3) Uani 1 1 d .
C16 C 0.56981(14) 0.17416(8) 0.20492(12) 0.0408(3) Uani 1 1 d .
C12 C 0.48659(16) 0.04101(8) 0.27850(14) 0.0512(4) Uani 1 1 d .
H12 H 0.4863 -0.0006 0.3411 0.061 Uiso 1 1 calc R
C20 C 0.62211(16) 0.32782(8) 0.18145(14) 0.0497(4) Uani 1 1 d .
H20 H 0.5348 0.3453 0.1473 0.060 Uiso 1 1 calc R
C15 C 0.48951(15) 0.16229(9) 0.08983(13) 0.0492(4) Uani 1 1 d .
H15 H 0.4910 0.2027 0.0256 0.059 Uiso 1 1 calc R
C19 C 0.73574(16) 0.37806(9) 0.20114(15) 0.0542(4) Uani 1 1 d .
H19 H 0.7402 0.4358 0.1836 0.065 Uiso 1 1 calc R
C17 C 0.79578(15) 0.24662(9) 0.26343(13) 0.0490(4) Uani 1 1 d .
H17 H 0.8465 0.1997 0.2944 0.059 Uiso 1 1 calc R
C18 C 0.84565(16) 0.32660(9) 0.25291(14) 0.0524(4) Uani 1 1 d .
H18 H 0.9361 0.3442 0.2758 0.063 Uiso 1 1 calc R
C14 C 0.40756(16) 0.09099(9) 0.06986(14) 0.0551(4) Uani 1 1 d .
H14 H 0.3524 0.0842 -0.0067 0.066 Uiso 1 1 calc R
C13 C 0.40763(16) 0.02979(9) 0.16370(15) 0.0558(4) Uani 1 1 d .
H13 H 0.3544 -0.0190 0.1495 0.067 Uiso 1 1 calc R
C9 C 0.62552(13) 0.29583(8) 0.66700(12) 0.0400(3) Uani 1 1 d .
N1 N 0.54135(12) 0.34380(7) 0.58428(11) 0.0488(3) Uani 1 1 d .
C1 C 0.66869(13) 0.21497(8) 0.62358(11) 0.0393(3) Uani 1 1 d .
C5 C 0.66927(14) 0.32207(9) 0.79358(13) 0.0460(3) Uani 1 1 d .
C6 C 0.62284(17) 0.40214(10) 0.83188(15) 0.0590(4) Uani 1 1 d .
H6 H 0.6503 0.4226 0.9132 0.071 Uiso 1 1 calc R
C4 C 0.75502(16) 0.26776(10) 0.87387(14) 0.0538(4) Uani 1 1 d .
H4 H 0.7850 0.2845 0.9566 0.065 Uiso 1 1 calc R
C8 C 0.49920(17) 0.41728(9) 0.62689(16) 0.0587(4) Uani 1 1 d .
H8 H 0.4400 0.4500 0.5721 0.070 Uiso 1 1 calc R
C7 C 0.53795(18) 0.44908(10) 0.74950(16) 0.0637(4) Uani 1 1 d .
H7 H 0.5059 0.5016 0.7740 0.076 Uiso 1 1 calc R
N3 N 0.65754(11) 0.24690(6) 0.22042(10) 0.0415(3) Uani 1 1 d .
C10 C 0.64347(15) 0.12139(8) 0.43281(13) 0.0468(3) Uani 1 1 d .
N2 N 0.61896(12) 0.19324(7) 0.49805(10) 0.0442(3) Uani 1 1 d .
H2N H 0.5663 0.2301 0.4574 0.053 Uiso 1 1 calc R
O1 O 0.71664(15) 0.06372(7) 0.47740(11) 0.0799(4) Uani 1 1 d .
C2 C 0.75074(14) 0.16380(9) 0.70513(13) 0.0460(3) Uani 1 1 d .
H2 H 0.7781 0.1108 0.6777 0.055 Uiso 1 1 calc R
C3 C 0.79339(15) 0.19111(10) 0.82975(14) 0.0538(4) Uani 1 1 d .
H3 H 0.8494 0.1558 0.8835 0.065 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
C12 C11 C16 118.45(13)
C12 C11 C10 116.67(12)
C16 C11 C10 124.87(12)
C15 C16 C11 119.86(12)
C15 C16 N3 119.11(11)
C11 C16 N3 121.01(12)
C13 C12 C11 121.13(13)
C19 C20 N3 108.63(13)
C14 C15 C16 120.61(13)
C20 C19 C18 107.32(13)
C18 C17 N3 108.34(13)
C17 C18 C19 107.65(13)
C13 C14 C15 119.91(14)
C12 C13 C14 119.97(13)
N1 C9 C5 122.98(12)
N1 C9 C1 117.75(11)
C5 C9 C1 119.26(12)
C8 N1 C9 117.07(12)
C2 C1 N2 124.78(12)
C2 C1 C9 119.54(12)
N2 C1 C9 115.66(11)
C6 C5 C4 123.73(13)
C6 C5 C9 116.95(13)
C4 C5 C9 119.32(13)
C7 C6 C5 119.71(14)
C3 C4 C5 119.86(13)
N1 C8 C7 124.16(15)
C6 C7 C8 119.11(14)
C20 N3 C17 108.06(11)
C20 N3 C16 125.57(12)
C17 N3 C16 126.00(11)
O1 C10 N2 123.43(13)
O1 C10 C11 120.74(12)
N2 C10 C11 115.72(11)
C10 N2 C1 128.19(11)
C1 C2 C3 120.30(13)
C4 C3 C2 121.71(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C11 C12 1.3952(19)
C11 C16 1.4011(18)
C11 C10 1.5020(19)
C16 C15 1.3886(19)
C16 N3 1.4276(16)
C12 C13 1.379(2)
C20 C19 1.357(2)
C20 N3 1.3727(16)
C15 C14 1.381(2)
C19 C18 1.407(2)
C17 C18 1.3580(19)
C17 N3 1.3743(19)
C14 C13 1.380(2)
C9 N1 1.3638(17)
C9 C5 1.4202(18)
C9 C1 1.4297(18)
N1 C8 1.3205(18)
C1 C2 1.3746(18)
C1 N2 1.4048(16)
C5 C6 1.411(2)
C5 C4 1.416(2)
C6 C7 1.357(2)
C4 C3 1.359(2)
C8 C7 1.402(2)
C10 O1 1.2189(16)
C10 N2 1.3568(16)
C2 C3 1.404(2)
