#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:51:22 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230630 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/63/7156325.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_7156325
loop_
_publ_author_name
'Zhang, Wei'
'Yang, Chen'
'Pan, Yu-Liang'
'Li, Xin'
'Cheng, Jin-Pei'
_publ_section_title
;
 Synthesis of 3-cyanomethylated coumarins by a visible-light-mediated
 direct cyanomethylation of aryl alkynoates.
;
_journal_issue                   32
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5788
_journal_page_last               5792
_journal_paper_doi               10.1039/c8ob01513a
_journal_volume                  16
_journal_year                    2018
_chemical_formula_sum            'C17 H10 Br N O2'
_chemical_formula_weight         340.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/8
_audit_update_record
;
2018-06-24 deposited with the CCDC.
2018-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.76(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.067(2)
_cell_length_b                   9.1332(18)
_cell_length_c                   15.755(3)
_cell_measurement_reflns_used    3709
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.8984
_cell_measurement_theta_min      2.0829
_cell_volume                     1407.0(5)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_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      113(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_av_unetI/netI     0.0832
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14569
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.886
_diffrn_reflns_theta_min         2.189
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.924
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_description       bulk
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.693
_refine_diff_density_min         -1.023
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0285P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0824
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2002
_reflns_number_total             3348
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ob01513a2.cif
_cod_data_source_block           shelxl_CCDC1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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 

 Adding full bibliography for 7156324--7156325.cif.
;
_cod_original_cell_volume        1406.9(5)
_cod_database_code               7156325
_shelx_shelxl_version_number     2014/8
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.592
_shelx_estimated_absorpt_t_max   0.720
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Br1 Br 0.14954(3) -0.39711(3) 1.06758(2) 0.02852(11) Uani 1 1 d . .
O1 O -0.12175(17) -0.0315(2) 0.83630(13) 0.0263(5) Uani 1 1 d . .
O2 O -0.25362(19) 0.1131(2) 0.73905(14) 0.0336(5) Uani 1 1 d . .
N1 N -0.0579(4) 0.2828(4) 0.5681(2) 0.0775(12) Uani 1 1 d . .
C1 C 0.0052(3) -0.0688(3) 0.88831(19) 0.0223(7) Uani 1 1 d . .
C2 C 0.0094(3) -0.1934(3) 0.93932(18) 0.0247(7) Uani 1 1 d . .
H2 H -0.0703 -0.2497 0.9380 0.030 Uiso 1 1 calc R U
C3 C 0.1354(3) -0.2319(3) 0.99229(18) 0.0244(7) Uani 1 1 d . .
C4 C 0.2530(3) -0.1511(3) 0.9941(2) 0.0274(7) Uani 1 1 d . .
H4 H 0.3381 -0.1805 1.0305 0.033 Uiso 1 1 calc R U
C5 C 0.2449(3) -0.0286(3) 0.94297(18) 0.0250(7) Uani 1 1 d . .
H5 H 0.3254 0.0266 0.9445 0.030 Uiso 1 1 calc R U
C6 C 0.1202(3) 0.0172(3) 0.88818(18) 0.0203(7) Uani 1 1 d . .
C7 C 0.1038(3) 0.1486(3) 0.83550(19) 0.0207(7) Uani 1 1 d . .
C8 C -0.0219(3) 0.1857(3) 0.78712(18) 0.0214(7) Uani 1 1 d . .
C9 C -0.1399(3) 0.0923(3) 0.7845(2) 0.0238(7) Uani 1 1 d . .
C10 C -0.0514(3) 0.3221(3) 0.73245(19) 0.0267(7) Uani 1 1 d . .
H10A H -0.1400 0.3631 0.7381 0.032 Uiso 1 1 calc R U
H10B H 0.0203 0.3955 0.7558 0.032 Uiso 1 1 calc R U
C11 C -0.0572(3) 0.2986(4) 0.6398(2) 0.0405(9) Uani 1 1 d . .
C12 C 0.2271(3) 0.2419(3) 0.83855(18) 0.0208(7) Uani 1 1 d . .
C13 C 0.2431(3) 0.3724(3) 0.8849(2) 0.0286(7) Uani 1 1 d . .
H13 H 0.1729 0.4050 0.9114 0.034 Uiso 1 1 calc R U
C14 C 0.3614(3) 0.4562(4) 0.8930(2) 0.0360(8) Uani 1 1 d . .
H14 H 0.3721 0.5454 0.9249 0.043 Uiso 1 1 calc R U
C15 C 0.4627(3) 0.4079(4) 0.8542(2) 0.0372(9) Uani 1 1 d . .
H15 H 0.5438 0.4641 0.8600 0.045 Uiso 1 1 calc R U
C16 C 0.4480(3) 0.2799(4) 0.8073(2) 0.0382(9) Uani 1 1 d . .
H16 H 0.5179 0.2483 0.7802 0.046 Uiso 1 1 calc R U
C17 C 0.3292(3) 0.1962(4) 0.7996(2) 0.0303(8) Uani 1 1 d . .
H17 H 0.3188 0.1074 0.7673 0.036 Uiso 1 1 calc R U
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'
Br Br -0.2901 2.4595 '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
C9 O1 C1 121.6(2)
O1 C1 C2 116.2(2)
O1 C1 C6 120.5(3)
C2 C1 C6 123.3(3)
C3 C2 C1 117.0(3)
C3 C2 H2 121.5
C1 C2 H2 121.5
C2 C3 C4 122.0(3)
C2 C3 Br1 119.9(2)
C4 C3 Br1 118.1(2)
C5 C4 C3 119.4(3)
C5 C4 H4 120.3
C3 C4 H4 120.3
C4 C5 C6 121.5(3)
C4 C5 H5 119.2
C6 C5 H5 119.2
C1 C6 C5 116.7(3)
C1 C6 C7 119.0(2)
C5 C6 C7 124.2(3)
C8 C7 C6 119.6(3)
C8 C7 C12 122.1(3)
C6 C7 C12 118.3(2)
C7 C8 C9 121.0(3)
C7 C8 C10 124.1(3)
C9 C8 C10 114.9(2)
O2 C9 O1 116.8(3)
O2 C9 C8 125.1(3)
O1 C9 C8 118.1(2)
C11 C10 C8 114.0(3)
C11 C10 H10A 108.8
C8 C10 H10A 108.8
C11 C10 H10B 108.8
C8 C10 H10B 108.8
H10A C10 H10B 107.7
N1 C11 C10 177.8(4)
C17 C12 C13 119.2(3)
C17 C12 C7 120.8(3)
C13 C12 C7 119.9(3)
C12 C13 C14 120.6(3)
C12 C13 H13 119.7
C14 C13 H13 119.7
C15 C14 C13 119.2(3)
C15 C14 H14 120.4
C13 C14 H14 120.4
C16 C15 C14 121.0(3)
C16 C15 H15 119.5
C14 C15 H15 119.5
C15 C16 C17 119.5(3)
C15 C16 H16 120.2
C17 C16 H16 120.2
C12 C17 C16 120.5(3)
C12 C17 H17 119.8
C16 C17 H17 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C3 1.904(3)
O1 C9 1.381(3)
O1 C1 1.386(3)
O2 C9 1.212(3)
N1 C11 1.138(4)
C1 C2 1.388(4)
C1 C6 1.399(4)
C2 C3 1.387(4)
C2 H2 0.9500
C3 C4 1.390(4)
C4 C5 1.369(4)
C4 H4 0.9500
C5 C6 1.408(4)
C5 H5 0.9500
C6 C7 1.446(4)
C7 C8 1.356(4)
C7 C12 1.497(4)
C8 C9 1.455(4)
C8 C10 1.503(4)
C10 C11 1.463(5)
C10 H10A 0.9900
C10 H10B 0.9900
C12 C17 1.382(4)
C12 C13 1.387(4)
C13 C14 1.396(4)
C13 H13 0.9500
C14 C15 1.380(5)
C14 H14 0.9500
C15 C16 1.372(5)
C15 H15 0.9500
C16 C17 1.400(4)
C16 H16 0.9500
C17 H17 0.9500
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
C9 O1 C1 C2 178.2(3)
C9 O1 C1 C6 -1.5(4)
O1 C1 C2 C3 -179.6(2)
C6 C1 C2 C3 0.1(4)
C1 C2 C3 C4 -0.6(4)
C1 C2 C3 Br1 177.7(2)
C2 C3 C4 C5 0.7(5)
Br1 C3 C4 C5 -177.7(2)
C3 C4 C5 C6 -0.2(5)
O1 C1 C6 C5 180.0(2)
C2 C1 C6 C5 0.4(4)
O1 C1 C6 C7 2.3(4)
C2 C1 C6 C7 -177.3(3)
C4 C5 C6 C1 -0.3(4)
C4 C5 C6 C7 177.3(3)
C1 C6 C7 C8 -0.2(4)
C5 C6 C7 C8 -177.7(3)
C1 C6 C7 C12 177.9(3)
C5 C6 C7 C12 0.4(4)
C6 C7 C8 C9 -2.6(4)
C12 C7 C8 C9 179.3(3)
C6 C7 C8 C10 177.9(3)
C12 C7 C8 C10 -0.2(4)
C1 O1 C9 O2 177.6(2)
C1 O1 C9 C8 -1.3(4)
C7 C8 C9 O2 -175.4(3)
C10 C8 C9 O2 4.2(4)
C7 C8 C9 O1 3.4(4)
C10 C8 C9 O1 -177.1(2)
C7 C8 C10 C11 98.1(3)
C9 C8 C10 C11 -81.4(3)
C8 C7 C12 C17 -109.8(3)
C6 C7 C12 C17 72.0(4)
C8 C7 C12 C13 73.6(4)
C6 C7 C12 C13 -104.5(3)
C17 C12 C13 C14 -0.7(4)
C7 C12 C13 C14 176.0(3)
C12 C13 C14 C15 0.1(5)
C13 C14 C15 C16 0.6(5)
C14 C15 C16 C17 -0.7(5)
C13 C12 C17 C16 0.5(4)
C7 C12 C17 C16 -176.1(3)
C15 C16 C17 C12 0.2(5)
