#------------------------------------------------------------------------------
#$Date: 2017-04-19 04:54:55 +0300 (Wed, 19 Apr 2017) $
#$Revision: 195528 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/99/7119983.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_7119983
loop_
_publ_author_name
'Ding, Dong'
'Mou, Tao'
'Xue, Jiahui'
'Jiang, Xuefeng'
_publ_section_title
;
 Access to Divergent Benzo-Heterocycles via a Catalyst-Dependent Strategy
 in the Controllable Cyclization of o-Alkynyl-N-methoxyl-benzamides
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC01861D
_journal_year                    2017
_chemical_formula_sum            'C16 H13 N O2'
_chemical_formula_weight         251.27
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_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
_audit_update_record
;
2016-11-07 deposited with the CCDC.
2017-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 102.745(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   30.495(3)
_cell_length_b                   4.1711(4)
_cell_length_c                   20.4558(19)
_cell_measurement_reflns_used    2983
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.13
_cell_measurement_theta_min      2.19
_cell_volume                     2537.8(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart Apex II CCD'
_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  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13654
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.37
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9819
_exptl_absorpt_correction_T_min  0.9585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.092
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.026
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2212
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0342
_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)+(0.0444P)²+0.4118P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0919
_reflns_number_gt                1616
_reflns_number_total             2212
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc01861d2.cif
_cod_data_source_block           z
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7119983
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
O1 O 0.15858(3) 0.8179(3) 0.05782(5) 0.0532(3) Uani 1 1 d .
O2 O 0.23967(3) 0.9759(3) 0.06337(5) 0.0711(4) Uani 1 1 d .
N1 N 0.23315(4) 0.7939(3) 0.11820(6) 0.0598(4) Uani 1 1 d .
C1 C 0.12574(5) 0.5372(3) 0.13091(7) 0.0477(4) Uani 1 1 d .
C2 C 0.09672(5) 0.3858(4) 0.16490(8) 0.0585(4) Uani 1 1 d .
H2A H 0.0659 0.3807 0.1472 0.070 Uiso 1 1 calc R
C3 C 0.11505(6) 0.2439(4) 0.22543(8) 0.0653(5) Uani 1 1 d .
H3A H 0.0963 0.1413 0.2490 0.078 Uiso 1 1 calc R
C4 C 0.16094(6) 0.2506(4) 0.25208(8) 0.0661(5) Uani 1 1 d .
H4A H 0.1724 0.1509 0.2929 0.079 Uiso 1 1 calc R
C5 C 0.18982(6) 0.4021(4) 0.21919(8) 0.0617(4) Uani 1 1 d .
H5A H 0.2206 0.4086 0.2373 0.074 Uiso 1 1 calc R
C6 C 0.17145(5) 0.5445(3) 0.15816(7) 0.0494(4) Uani 1 1 d .
C7 C 0.19182(5) 0.7246(4) 0.11167(7) 0.0499(4) Uani 1 1 d .
C8 C 0.11713(5) 0.7087(3) 0.06753(7) 0.0471(4) Uani 1 1 d .
C9 C 0.07874(5) 0.7636(3) 0.02330(7) 0.0500(4) Uani 1 1 d .
H9A H 0.0533 0.6798 0.0352 0.060 Uiso 1 1 calc R
C10 C 0.06985(5) 0.9330(3) -0.04060(7) 0.0472(4) Uani 1 1 d .
C11 C 0.10279(5) 1.0862(4) -0.06705(7) 0.0555(4) Uani 1 1 d .
H11A H 0.1325 1.0854 -0.0430 0.067 Uiso 1 1 calc R
C12 C 0.09191(5) 1.2384(4) -0.12820(7) 0.0599(4) Uani 1 1 d .
H12A H 0.1143 1.3387 -0.1451 0.072 Uiso 1 1 calc R
C13 C 0.04824(5) 1.2436(4) -0.16462(8) 0.0610(4) Uani 1 1 d .
H13A H 0.0411 1.3466 -0.2059 0.073 Uiso 1 1 calc R
C14 C 0.01536(5) 1.0954(4) -0.13936(8) 0.0638(5) Uani 1 1 d .
H14A H -0.0142 1.0974 -0.1637 0.077 Uiso 1 1 calc R
C15 C 0.02595(5) 0.9438(4) -0.07820(7) 0.0559(4) Uani 1 1 d .
H15A H 0.0032 0.8463 -0.0616 0.067 Uiso 1 1 calc R
C16 C 0.28603(5) 1.0534(5) 0.07300(9) 0.0792(6) Uani 1 1 d .
H16A H 0.2908 1.1772 0.0356 0.119 Uiso 1 1 calc R
H16B H 0.3034 0.8596 0.0764 0.119 Uiso 1 1 calc R
H16C H 0.2952 1.1758 0.1135 0.119 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
C7 O1 C8 108.84(11)
N1 O2 C16 108.91(11)
C7 N1 O2 110.54(11)
C6 C1 C2 120.27(14)
C6 C1 C8 108.45(12)
C2 C1 C8 131.28(14)
C3 C2 C1 117.93(15)
C3 C2 H2A 121.0
C1 C2 H2A 121.0
C2 C3 C4 121.34(15)
C2 C3 H3A 119.3
C4 C3 H3A 119.3
C5 C4 C3 121.17(15)
C5 C4 H4A 119.4
C3 C4 H4A 119.4
C4 C5 C6 117.59(15)
C4 C5 H5A 121.2
C6 C5 H5A 121.2
C1 C6 C5 121.71(14)
C1 C6 C7 106.60(12)
C5 C6 C7 131.68(14)
N1 C7 O1 123.86(13)
N1 C7 C6 127.26(13)
O1 C7 C6 108.87(12)
C9 C8 O1 122.29(13)
C9 C8 C1 130.48(13)
O1 C8 C1 107.23(11)
C8 C9 C10 130.84(13)
C8 C9 H9A 114.6
C10 C9 H9A 114.6
C15 C10 C11 117.27(14)
C15 C10 C9 118.55(13)
C11 C10 C9 124.18(13)
C12 C11 C10 120.88(14)
C12 C11 H11A 119.6
C10 C11 H11A 119.6
C13 C12 C11 120.67(15)
C13 C12 H12A 119.7
C11 C12 H12A 119.7
C14 C13 C12 119.32(15)
C14 C13 H13A 120.3
C12 C13 H13A 120.3
C13 C14 C15 120.34(14)
C13 C14 H14A 119.8
C15 C14 H14A 119.8
C14 C15 C10 121.51(15)
C14 C15 H15A 119.2
C10 C15 H15A 119.2
O2 C16 H16A 109.5
O2 C16 H16B 109.5
H16A C16 H16B 109.5
O2 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.3784(16)
O1 C8 1.3981(16)
O2 N1 1.4042(16)
O2 C16 1.4209(18)
N1 C7 1.2712(18)
C1 C6 1.383(2)
C1 C2 1.392(2)
C1 C8 1.4530(19)
C2 C3 1.375(2)
C2 H2A 0.9300
C3 C4 1.386(2)
C3 H3A 0.9300
C4 C5 1.374(2)
C4 H4A 0.9300
C5 C6 1.384(2)
C5 H5A 0.9300
C6 C7 1.454(2)
C8 C9 1.3321(19)
C9 C10 1.4576(19)
C9 H9A 0.9300
C10 C15 1.3897(19)
C10 C11 1.397(2)
C11 C12 1.376(2)
C11 H11A 0.9300
C12 C13 1.375(2)
C12 H12A 0.9300
C13 C14 1.372(2)
C13 H13A 0.9300
C14 C15 1.375(2)
C14 H14A 0.9300
C15 H15A 0.9300
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
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
C16 O2 N1 C7 178.96(14)
C6 C1 C2 C3 -0.5(2)
C8 C1 C2 C3 -179.33(15)
C1 C2 C3 C4 0.0(2)
C2 C3 C4 C5 0.6(3)
C3 C4 C5 C6 -0.7(2)
C2 C1 C6 C5 0.4(2)
C8 C1 C6 C5 179.45(13)
C2 C1 C6 C7 -178.67(12)
C8 C1 C6 C7 0.42(15)
C4 C5 C6 C1 0.2(2)
C4 C5 C6 C7 178.97(15)
O2 N1 C7 O1 0.0(2)
O2 N1 C7 C6 -178.92(13)
C8 O1 C7 N1 -178.48(14)
C8 O1 C7 C6 0.61(15)
C1 C6 C7 N1 178.40(15)
C5 C6 C7 N1 -0.5(3)
C1 C6 C7 O1 -0.64(15)
C5 C6 C7 O1 -179.53(15)
C7 O1 C8 C9 -179.99(13)
C7 O1 C8 C1 -0.34(15)
C6 C1 C8 C9 179.54(15)
C2 C1 C8 C9 -1.5(3)
C6 C1 C8 O1 -0.07(15)
C2 C1 C8 O1 178.89(14)
O1 C8 C9 C10 0.1(2)
C1 C8 C9 C10 -179.43(13)
C8 C9 C10 C15 177.65(15)
C8 C9 C10 C11 -2.2(2)
C15 C10 C11 C12 -0.6(2)
C9 C10 C11 C12 179.24(13)
C10 C11 C12 C13 0.2(2)
C11 C12 C13 C14 0.1(2)
C12 C13 C14 C15 0.2(2)
C13 C14 C15 C10 -0.6(2)
C11 C10 C15 C14 0.8(2)
C9 C10 C15 C14 -179.01(14)
