#------------------------------------------------------------------------------
#$Date: 2019-11-24 15:42:41 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238396 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/52/1555216.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_1555216
loop_
_publ_author_name
'Jia, Feng-Cheng'
'Zhou, Zhi-Wen'
'Xu, Cheng'
'Cai, Qun'
'Li, Deng-Kui'
'Wu, An-Xin'
_publ_section_title
;
 Expeditious Synthesis of 2-Phenylquinazolin-4-amines via a Fe/Cu
 Relay-Catalyzed Domino Strategy.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4236
_journal_page_last               4239
_journal_paper_doi               10.1021/acs.orglett.5b02020
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C14 H11 N3'
_chemical_formula_weight         221.26
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 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                 106.898(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.857(4)
_cell_length_b                   12.127(3)
_cell_length_c                   13.289(4)
_cell_measurement_reflns_used    8222
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      32.00
_cell_measurement_theta_min      2.21
_cell_volume                     2290.9(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9807
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.21
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9921
_exptl_absorpt_correction_T_min  0.9843
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2761
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0674P)²+1.3927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1202
_reflns_number_gt                2560
_reflns_number_total             2761
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol5b02020_si_001.cif
_cod_data_source_block           g:\150113l\work\mo_150113l_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        2291.0(10)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1555216
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C1 C 0.21867(6) 1.02919(8) 0.21653(7) 0.0159(2) Uani 1 1 d .
C2 C 0.27962(7) 1.10228(8) 0.28706(8) 0.0196(2) Uani 1 1 d .
H2 H 0.2686 1.1201 0.3521 0.024 Uiso 1 1 calc R
C3 C 0.35513(7) 1.14781(9) 0.26169(9) 0.0226(2) Uani 1 1 d .
H3 H 0.3963 1.1967 0.3094 0.027 Uiso 1 1 calc R
C4 C 0.37129(7) 1.12209(9) 0.16521(9) 0.0235(2) Uani 1 1 d .
H4 H 0.4229 1.1548 0.1477 0.028 Uiso 1 1 calc R
C5 C 0.31335(7) 1.05015(9) 0.09594(8) 0.0209(2) Uani 1 1 d .
H5 H 0.3253 1.0332 0.0312 0.025 Uiso 1 1 calc R
C6 C 0.23600(6) 1.00138(8) 0.12061(7) 0.0161(2) Uani 1 1 d .
C7 C 0.10367(6) 0.89417(8) 0.07323(7) 0.0148(2) Uani 1 1 d .
C8 C 0.13505(7) 0.98193(8) 0.23364(7) 0.0164(2) Uani 1 1 d .
C9 C 0.04107(7) 0.81517(8) -0.00052(7) 0.0161(2) Uani 1 1 d .
C10 C 0.07919(7) 0.73801(9) -0.05462(8) 0.0229(2) Uani 1 1 d .
H10 H 0.1448 0.7383 -0.0471 0.027 Uiso 1 1 calc R
C11 C 0.02128(8) 0.66086(10) -0.11932(9) 0.0296(3) Uani 1 1 d .
H11 H 0.0477 0.6075 -0.1548 0.036 Uiso 1 1 calc R
C12 C -0.07507(8) 0.66093(9) -0.13270(9) 0.0278(3) Uani 1 1 d .
H12 H -0.1143 0.6081 -0.1774 0.033 Uiso 1 1 calc R
C13 C -0.11369(7) 0.73848(9) -0.08054(8) 0.0229(2) Uani 1 1 d .
H13 H -0.1797 0.7398 -0.0906 0.028 Uiso 1 1 calc R
C14 C -0.05583(7) 0.81419(8) -0.01358(8) 0.0190(2) Uani 1 1 d .
H14 H -0.0823 0.8657 0.0237 0.023 Uiso 1 1 calc R
N1 N 0.17901(6) 0.92963(7) 0.04909(6) 0.01646(19) Uani 1 1 d .
N2 N 0.07708(6) 0.91926(7) 0.16021(6) 0.01644(19) Uani 1 1 d .
N3 N 0.11198(6) 0.99878(8) 0.32231(7) 0.0225(2) Uani 1 1 d D
H3B H 0.1464(9) 1.0377(11) 0.3748(9) 0.027 Uiso 1 1 d D
H3A H 0.0608(8) 0.9682(11) 0.3297(11) 0.027 Uiso 1 1 d 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 119.95(9)
C2 C1 C8 124.04(9)
C6 C1 C8 115.97(8)
C3 C2 C1 120.03(9)
C3 C2 H2 120.0
C1 C2 H2 120.0
C2 C3 C4 120.08(9)
C2 C3 H3 120.0
C4 C3 H3 120.0
C5 C4 C3 120.78(9)
C5 C4 H4 119.6
C3 C4 H4 119.6
C4 C5 C6 120.23(9)
C4 C5 H5 119.9
C6 C5 H5 119.9
N1 C6 C1 122.34(9)
N1 C6 C5 118.75(9)
C1 C6 C5 118.90(9)
N1 C7 N2 127.49(9)
N1 C7 C9 117.43(8)
N2 C7 C9 115.05(8)
N3 C8 N2 117.10(9)
N3 C8 C1 122.09(9)
N2 C8 C1 120.81(9)
C10 C9 C14 119.15(9)
C10 C9 C7 120.08(9)
C14 C9 C7 120.72(8)
C11 C10 C9 119.98(10)
C11 C10 H10 120.0
C9 C10 H10 120.0
C10 C11 C12 120.59(10)
C10 C11 H11 119.7
C12 C11 H11 119.7
C13 C12 C11 119.76(10)
C13 C12 H12 120.1
C11 C12 H12 120.1
C12 C13 C14 119.96(10)
C12 C13 H13 120.0
C14 C13 H13 120.0
C13 C14 C9 120.53(9)
C13 C14 H14 119.7
C9 C14 H14 119.7
C7 N1 C6 115.50(8)
C8 N2 C7 117.61(8)
C8 N3 H3B 123.1(9)
C8 N3 H3A 119.2(10)
H3B N3 H3A 117.7(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.4110(13)
C1 C6 1.4126(13)
C1 C8 1.4449(13)
C2 C3 1.3772(15)
C2 H2 0.9500
C3 C4 1.4064(16)
C3 H3 0.9500
C4 C5 1.3743(15)
C4 H4 0.9500
C5 C6 1.4132(14)
C5 H5 0.9500
C6 N1 1.3819(12)
C7 N1 1.3227(13)
C7 N2 1.3602(12)
C7 C9 1.4878(13)
C8 N3 1.3352(13)
C8 N2 1.3353(13)
C9 C10 1.3964(14)
C9 C14 1.3992(14)
C10 C11 1.3874(15)
C10 H10 0.9500
C11 C12 1.3902(17)
C11 H11 0.9500
C12 C13 1.3876(16)
C12 H12 0.9500
C13 C14 1.3889(14)
C13 H13 0.9500
C14 H14 0.9500
N3 H3B 0.874(9)
N3 H3A 0.877(9)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3B N1 0.874(9) 2.259(11) 3.0139(14) 144.6(12) 6_576
N3 H3A N2 0.877(9) 2.174(9) 3.0420(14) 170.4(14) 2
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 C3 1.01(15)
C8 C1 C2 C3 -176.62(9)
C1 C2 C3 C4 0.39(16)
C2 C3 C4 C5 -1.10(16)
C3 C4 C5 C6 0.40(16)
C2 C1 C6 N1 179.51(8)
C8 C1 C6 N1 -2.68(13)
C2 C1 C6 C5 -1.68(14)
C8 C1 C6 C5 176.13(9)
C4 C5 C6 N1 179.84(9)
C4 C5 C6 C1 0.99(15)
C2 C1 C8 N3 -4.39(15)
C6 C1 C8 N3 177.90(9)
C2 C1 C8 N2 175.38(9)
C6 C1 C8 N2 -2.33(14)
N1 C7 C9 C10 34.05(13)
N2 C7 C9 C10 -144.30(9)
N1 C7 C9 C14 -148.43(9)
N2 C7 C9 C14 33.22(12)
C14 C9 C10 C11 -0.77(15)
C7 C9 C10 C11 176.79(10)
C9 C10 C11 C12 1.36(18)
C10 C11 C12 C13 -0.30(18)
C11 C12 C13 C14 -1.33(17)
C12 C13 C14 C9 1.91(15)
C10 C9 C14 C13 -0.86(14)
C7 C9 C14 C13 -178.40(9)
N2 C7 N1 C6 -0.82(14)
C9 C7 N1 C6 -178.94(8)
C1 C6 N1 C7 4.17(13)
C5 C6 N1 C7 -174.64(9)
N3 C8 N2 C7 -174.80(9)
C1 C8 N2 C7 5.41(14)
N1 C7 N2 C8 -4.01(15)
C9 C7 N2 C8 174.15(8)
