#------------------------------------------------------------------------------
#$Date: 2020-10-06 12:34:24 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257640 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/97/7059735.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_7059735
loop_
_publ_author_name
'He, Xinwei'
'Li, Ruxue'
'Xie, Mengqing'
'Duan, Jiahui'
'Tang, Qiang'
'Shang, Yongjia'
_publ_section_title
;
 Copper-catalyzed cascade three-component azide--alkyne
 cycloaddition/condensation/transesterification: easy access to
 3-triazolylcoumarins
;
_journal_issue                   28
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12266
_journal_page_last               12273
_journal_paper_doi               10.1039/D0NJ02100H
_journal_volume                  44
_journal_year                    2020
_chemical_formula_sum            'C17 H10 Cl N3 O2'
_chemical_formula_weight         323.73
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2020-04-22 deposited with the CCDC.	2020-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                85.0800(10)
_cell_angle_beta                 87.5620(10)
_cell_angle_gamma                78.9580(10)
_cell_formula_units_Z            2
_cell_length_a                   6.0960(7)
_cell_length_b                   7.6004(9)
_cell_length_c                   15.3686(18)
_cell_measurement_reflns_used    3596
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     696.05(14)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4982
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  0.9662
_exptl_absorpt_correction_T_min  0.9553
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2436
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0350
_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)+(0.0581P)²+0.1720P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1023
_reflns_number_gt                2159
_reflns_number_total             2436
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0nj02100h2.cif
_cod_data_source_block           141117a_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7059735.cif.

 Adding full bibliography for 7059735.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7059735
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 -0.2255(3) 0.7317(2) 0.11550(11) 0.0444(4) Uani 1 1 d . . .
C2 C 0.0031(3) 0.6813(2) 0.08047(10) 0.0382(3) Uani 1 1 d . . .
C3 C 0.1692(3) 0.5883(2) 0.12991(10) 0.0414(4) Uani 1 1 d . . .
H3 H 0.3136 0.5613 0.1063 0.050 Uiso 1 1 calc R . .
C4 C 0.1244(3) 0.5305(2) 0.21929(10) 0.0393(4) Uani 1 1 d . . .
C5 C 0.2882(3) 0.4351(2) 0.27531(10) 0.0454(4) Uani 1 1 d . . .
H5 H 0.4360 0.4050 0.2557 0.054 Uiso 1 1 calc R . .
C6 C 0.2275(3) 0.3864(2) 0.36005(11) 0.0451(4) Uani 1 1 d . . .
C7 C 0.0074(3) 0.4254(2) 0.39020(11) 0.0472(4) Uani 1 1 d . . .
H7 H -0.0302 0.3880 0.4472 0.057 Uiso 1 1 calc R . .
C8 C -0.1545(3) 0.5189(2) 0.33594(11) 0.0481(4) Uani 1 1 d . . .
H8 H -0.3027 0.5459 0.3555 0.058 Uiso 1 1 calc R . .
C9 C -0.0941(3) 0.5725(2) 0.25149(10) 0.0402(4) Uani 1 1 d . . .
C10 C -0.0892(3) 0.8503(2) -0.06627(10) 0.0423(4) Uani 1 1 d . . .
H10 H -0.2313 0.9165 -0.0557 0.051 Uiso 1 1 calc R . .
C11 C 0.0324(3) 0.8489(2) -0.14252(10) 0.0386(3) Uani 1 1 d . . .
C12 C -0.0265(3) 0.9442(2) -0.22806(10) 0.0384(4) Uani 1 1 d . . .
C13 C 0.1361(3) 0.9576(2) -0.29290(11) 0.0478(4) Uani 1 1 d . . .
H13 H 0.2850 0.9084 -0.2819 0.057 Uiso 1 1 calc R . .
C14 C 0.0777(3) 1.0439(3) -0.37398(12) 0.0549(5) Uani 1 1 d . . .
H14 H 0.1878 1.0526 -0.4171 0.066 Uiso 1 1 calc R . .
C15 C -0.1414(3) 1.1167(2) -0.39117(11) 0.0531(4) Uani 1 1 d . . .
H15 H -0.1799 1.1736 -0.4459 0.064 Uiso 1 1 calc R . .
C16 C -0.3034(3) 1.1052(2) -0.32733(12) 0.0549(5) Uani 1 1 d . . .
H16 H -0.4518 1.1553 -0.3388 0.066 Uiso 1 1 calc R . .
C17 C -0.2477(3) 1.0197(2) -0.24618(11) 0.0496(4) Uani 1 1 d . . .
H17 H -0.3588 1.0127 -0.2034 0.060 Uiso 1 1 calc R . .
Cl1 Cl 0.42764(8) 0.27541(7) 0.43320(3) 0.0653(2) Uani 1 1 d . . .
N1 N 0.0407(2) 0.73499(17) -0.00907(8) 0.0386(3) Uani 1 1 d . . .
N2 N 0.2364(2) 0.6628(2) -0.04884(9) 0.0504(4) Uani 1 1 d . . .
N3 N 0.2306(2) 0.7322(2) -0.12945(9) 0.0499(4) Uani 1 1 d . . .
O1 O -0.26077(19) 0.67037(16) 0.20027(7) 0.0478(3) Uani 1 1 d . . .
O2 O -0.3820(2) 0.8205(2) 0.07803(8) 0.0647(4) Uani 1 1 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
O2 C1 O1 117.36(15) . . ?
O2 C1 C2 126.91(15) . . ?
O1 C1 C2 115.73(14) . . ?
C3 C2 N1 121.41(14) . . ?
C3 C2 C1 121.92(14) . . ?
N1 C2 C1 116.67(13) . . ?
C2 C3 C4 120.10(15) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C9 C4 C5 118.45(14) . . ?
C9 C4 C3 117.92(14) . . ?
C5 C4 C3 123.63(15) . . ?
C6 C5 C4 119.02(16) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C7 121.60(16) . . ?
C5 C6 Cl1 120.57(14) . . ?
C7 C6 Cl1 117.83(13) . . ?
C8 C7 C6 119.88(15) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 118.88(16) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
O1 C9 C8 116.85(14) . . ?
O1 C9 C4 121.03(14) . . ?
C8 C9 C4 122.12(15) . . ?
N1 C10 C11 105.27(14) . . ?
N1 C10 H10 127.4 . . ?
C11 C10 H10 127.4 . . ?
C10 C11 N3 108.09(14) . . ?
C10 C11 C12 129.68(15) . . ?
N3 C11 C12 122.19(14) . . ?
C13 C12 C17 118.62(15) . . ?
C13 C12 C11 120.87(14) . . ?
C17 C12 C11 120.50(14) . . ?
C14 C13 C12 120.31(16) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 120.45(17) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 119.73(16) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 120.49(17) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C12 120.40(16) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
C10 N1 N2 110.18(13) . . ?
C10 N1 C2 131.13(13) . . ?
N2 N1 C2 118.69(12) . . ?
N3 N2 N1 107.05(13) . . ?
N2 N3 C11 109.41(13) . . ?
C1 O1 C9 123.22(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O2 1.196(2) . ?
C1 O1 1.368(2) . ?
C1 C2 1.465(2) . ?
C2 C3 1.342(2) . ?
C2 N1 1.423(2) . ?
C3 C4 1.437(2) . ?
C3 H3 0.9300 . ?
C4 C9 1.389(2) . ?
C4 C5 1.397(2) . ?
C5 C6 1.378(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.386(2) . ?
C6 Cl1 1.7388(17) . ?
C7 C8 1.369(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.383(2) . ?
C8 H8 0.9300 . ?
C9 O1 1.3723(19) . ?
C10 N1 1.353(2) . ?
C10 C11 1.359(2) . ?
C10 H10 0.9300 . ?
C11 N3 1.366(2) . ?
C11 C12 1.469(2) . ?
C12 C13 1.387(2) . ?
C12 C17 1.391(2) . ?
C13 C14 1.385(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.380(2) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
N1 N2 1.3574(19) . ?
N2 N3 1.303(2) . ?
