#------------------------------------------------------------------------------
#$Date: 2016-03-26 12:38:20 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180230 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/16/7111615.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7111615
loop_
_publ_author_name
'Zhang, Jintang'
'Yu, Chenmin'
'Wang, Sujing'
'Wan, Changfeng'
'Wang, Zhiyong'
_publ_section_title
;
 A novel and efficient methodology for the construction of quinazolines
 based on supported copper oxide nanoparticles
;
_journal_issue                   29
_journal_name_full               'Chemical Communications'
_journal_page_first              5244
_journal_page_last               5246
_journal_paper_doi               10.1039/c002454f
_journal_volume                  46
_journal_year                    2010
_chemical_formula_sum            'C20 H14 N2'
_chemical_formula_weight         282.33
_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                 99.74
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.633
_cell_length_b                   6.965
_cell_length_c                   19.786
_cell_measurement_reflns_used    5161
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      36.2331
_cell_measurement_theta_min      3.0784
_cell_volume                     1444.206
_computing_cell_refinement       CrysAlisPro
_computing_data_collection       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12899
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9611
_exptl_absorpt_correction_T_min  0.9553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov 6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.52
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0376
_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)+(0.0450P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0915
_reflns_number_gt                1781
_reflns_number_total             2945
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C002454Fsup1.cif
_cod_data_source_block           091207
_cod_original_cell_volume        1444.2
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7111615
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
N2 N 0.22421(9) 0.19192(13) 0.17267(5) 0.0423(2) Uani 1 1 d .
C2 C 0.28615(11) 0.19348(15) 0.29522(6) 0.0391(3) Uani 1 1 d .
N1 N 0.44544(8) 0.19863(13) 0.22151(5) 0.0423(2) Uani 1 1 d .
C3 C 0.25658(11) 0.18933(15) 0.10895(6) 0.0410(3) Uani 1 1 d .
C4 C 0.31811(11) 0.19512(15) 0.22497(6) 0.0386(3) Uani 1 1 d .
C5 C 0.38519(11) 0.19526(15) 0.09935(6) 0.0400(3) Uani 1 1 d .
C6 C 0.47813(10) 0.20193(15) 0.16017(6) 0.0397(3) Uani 1 1 d .
C7 C 0.15984(11) 0.20707(17) 0.30453(6) 0.0494(3) Uani 1 1 d .
H7 H 0.0953 0.2181 0.2666 0.059 Uiso 1 1 calc R
C8 C 0.41211(12) 0.18432(17) 0.03195(6) 0.0507(3) Uani 1 1 d .
H8 H 0.4963 0.1876 0.0248 0.061 Uiso 1 1 calc R
C9 C 0.61739(11) 0.20590(17) 0.15861(6) 0.0437(3) Uani 1 1 d .
C10 C 0.12959(13) 0.20432(18) 0.36945(7) 0.0569(4) Uani 1 1 d .
H10 H 0.0448 0.2144 0.3751 0.068 Uiso 1 1 calc R
C11 C 0.15911(12) 0.17564(16) 0.05131(6) 0.0513(3) Uani 1 1 d .
H11 H 0.0742 0.1737 0.0572 0.062 Uiso 1 1 calc R
C12 C 0.22295(14) 0.18687(17) 0.42565(7) 0.0581(4) Uani 1 1 d .
H12 H 0.2019 0.1845 0.4694 0.070 Uiso 1 1 calc R
C13 C 0.18824(13) 0.16523(17) -0.01267(7) 0.0565(4) Uani 1 1 d .
H13 H 0.1231 0.1554 -0.0503 0.068 Uiso 1 1 calc R
C14 C 0.37965(12) 0.17647(16) 0.35252(6) 0.0497(3) Uani 1 1 d .
H14 H 0.4648 0.1674 0.3474 0.060 Uiso 1 1 calc R
C15 C 0.31581(13) 0.16909(18) -0.02256(7) 0.0571(4) Uani 1 1 d .
H15 H 0.3346 0.1612 -0.0667 0.068 Uiso 1 1 calc R
C16 C 0.34820(13) 0.17277(18) 0.41711(7) 0.0589(4) Uani 1 1 d .
H16 H 0.4121 0.1606 0.4553 0.071 Uiso 1 1 calc R
C17 C 0.67097(12) 0.34066(18) 0.12060(6) 0.0548(3) Uani 1 1 d .
H17 H 0.6191 0.4310 0.0949 0.066 Uiso 1 1 calc R
C18 C 0.87783(13) 0.2099(3) 0.15774(7) 0.0738(5) Uani 1 1 d .
H18 H 0.9652 0.2108 0.1573 0.089 Uiso 1 1 calc R
C19 C 0.69671(12) 0.0744(2) 0.19699(6) 0.0562(4) Uani 1 1 d .
H19 H 0.6628 -0.0151 0.2238 0.067 Uiso 1 1 calc R
C20 C 0.80055(13) 0.3420(2) 0.12062(7) 0.0665(4) Uani 1 1 d .
H20 H 0.8355 0.4338 0.0951 0.080 Uiso 1 1 calc R
C21 C 0.82630(13) 0.0756(2) 0.19567(7) 0.0710(4) Uani 1 1 d .
H21 H 0.8788 -0.0153 0.2207 0.085 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C4 N2 C3 116.93(10)
C14 C2 C7 118.35(11)
C14 C2 C4 121.46(11)
C7 C2 C4 120.18(11)
C6 N1 C4 117.65(10)
N2 C3 C11 118.94(10)
N2 C3 C5 121.74(11)
C11 C3 C5 119.30(11)
N2 C4 N1 126.09(10)
N2 C4 C2 118.30(10)
N1 C4 C2 115.60(10)
C8 C5 C3 118.74(11)
C8 C5 C6 125.28(11)
C3 C5 C6 115.90(10)
N1 C6 C5 121.64(10)
N1 C6 C9 115.99(10)
C5 C6 C9 122.33(10)
C10 C7 C2 120.44(12)
C15 C8 C5 120.48(11)
C17 C9 C19 118.61(11)
C17 C9 C6 121.79(11)
C19 C9 C6 119.58(11)
C12 C10 C7 120.60(12)
C13 C11 C3 120.46(12)
C10 C12 C16 119.52(12)
C11 C13 C15 120.56(12)
C16 C14 C2 120.68(12)
C8 C15 C13 120.45(12)
C14 C16 C12 120.41(13)
C20 C17 C9 120.54(13)
C20 C18 C21 119.71(13)
C9 C19 C21 120.20(13)
C18 C20 C17 120.47(14)
C18 C21 C19 120.44(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N2 C4 1.3109(14)
N2 C3 1.3619(14)
C2 C14 1.3808(15)
C2 C7 1.3894(16)
C2 C4 1.4857(15)
N1 C6 1.3180(13)
N1 C4 1.3674(14)
C3 C11 1.4086(15)
C3 C5 1.4127(16)
C5 C8 1.4126(15)
C5 C6 1.4228(15)
C6 C9 1.4865(16)
C7 C10 1.3762(16)
C8 C15 1.3599(17)
C9 C17 1.3842(16)
C9 C19 1.3820(16)
C10 C12 1.3649(18)
C11 C13 1.3550(17)
C12 C16 1.3740(19)
C13 C15 1.4031(19)
C14 C16 1.3750(17)
C17 C20 1.3778(17)
C18 C20 1.363(2)
C18 C21 1.370(2)
C19 C21 1.3827(18)
