#------------------------------------------------------------------------------
#$Date: 2020-05-05 16:50:51 +0300 (Tue, 05 May 2020) $
#$Revision: 251731 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157424.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_7157424
loop_
_publ_author_name
'Ritu, ?'
'Sharma, Charu'
'Kumar, Sharvan'
'Jain, Nidhi'
_publ_section_title
;
 Singlet oxygen mediated dual C-C and C-N bond cleavage in visible light.
;
_journal_issue                   15
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2921
_journal_page_last               2928
_journal_paper_doi               10.1039/d0ob00563k
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C18 H14 N2 O3'
_chemical_formula_sum            'C18 H14 N2 O3'
_chemical_formula_weight         306.31
_chemical_name_common            'benzamide derivative'
_chemical_name_systematic        '4-(quinolin-2-ylcarbamoyl)phenyl acetate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-08-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-08 deposited with the CCDC.	2020-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.267(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5310(5)
_cell_length_b                   7.0315(4)
_cell_length_c                   21.6758(12)
_cell_measurement_reflns_used    9023
_cell_measurement_temperature    302(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.77
_cell_volume                     1450.29(14)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      302.56
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1525
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            62123
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.303
_diffrn_reflns_theta_min         2.140
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1292 before and 0.0454 after correction. The Ratio of minimum to maximum transmission is 0.9623. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_description       niddle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.10(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3561
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0707P)²+0.4398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1454
_refine_ls_wR_factor_ref         0.1482
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3304
_reflns_number_total             3561
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob00563k2.cif
_cod_data_source_block           new7_1_0m_a
_cod_depositor_comments          'Adding full bibliography for 7157424.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7157424
_shelx_shelxl_version_number     2014/7
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C16(H16), C12(H12), C2(H2A), C13(H13), C3(H3), C15(H15), C7(H7),
 C6(H6), C4(H4), C5(H5)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.41642(12) 1.15185(16) 0.66304(4) 0.0467(3) Uani 1 1 d . . . . .
N2 N 0.24721(12) 0.45440(16) 0.48030(5) 0.0381(3) Uani 1 1 d . . . . .
H2 H 0.3042 0.5322 0.4641 0.046 Uiso 1 1 calc R . . . .
O1 O 0.11885(15) 0.40680(18) 0.56408(6) 0.0636(4) Uani 1 1 d . . . . .
O3 O 0.52274(16) 1.30483(18) 0.58773(5) 0.0638(4) Uani 1 1 d . . . . .
N1 N 0.21847(12) 0.31188(16) 0.38569(5) 0.0366(3) Uani 1 1 d . . . . .
C11 C 0.26420(14) 0.67908(18) 0.56552(5) 0.0347(3) Uani 1 1 d . . . . .
C16 C 0.39717(14) 0.7475(2) 0.55439(6) 0.0393(3) Uani 1 1 d . . . . .
H16 H 0.4508 0.6852 0.5261 0.047 Uiso 1 1 calc R . . . .
C1 C 0.20842(13) 0.29248(18) 0.44558(6) 0.0343(3) Uani 1 1 d . . . . .
C12 C 0.18353(14) 0.7753(2) 0.60706(6) 0.0378(3) Uani 1 1 d . . . . .
H12 H 0.0946 0.7302 0.6149 0.045 Uiso 1 1 calc R . . . .
C8 C 0.18961(13) 0.15689(19) 0.34904(6) 0.0361(3) Uani 1 1 d . . . . .
C2 C 0.16800(15) 0.1213(2) 0.47427(6) 0.0405(3) Uani 1 1 d . . . . .
H2A H 0.1628 0.1142 0.5169 0.049 Uiso 1 1 calc R . . . .
C10 C 0.20334(14) 0.50093(19) 0.53738(6) 0.0390(3) Uani 1 1 d . . . . .
C14 C 0.36862(14) 0.99977(19) 0.62618(6) 0.0366(3) Uani 1 1 d . . . . .
C13 C 0.23452(15) 0.9369(2) 0.63669(6) 0.0398(3) Uani 1 1 d . . . . .
H13 H 0.1793 1.0030 0.6635 0.048 Uiso 1 1 calc R . . . .
C3 C 0.13702(16) -0.0320(2) 0.43786(7) 0.0425(3) Uani 1 1 d . . . . .
H3 H 0.1092 -0.1453 0.4556 0.051 Uiso 1 1 calc R . . . .
C15 C 0.45125(14) 0.9073(2) 0.58486(6) 0.0405(3) Uani 1 1 d . . . . .
H15 H 0.5409 0.9515 0.5777 0.049 Uiso 1 1 calc R . . . .
C9 C 0.14693(14) -0.0199(2) 0.37306(6) 0.0384(3) Uani 1 1 d . . . . .
C17 C 0.49313(16) 1.2955(2) 0.64035(7) 0.0425(3) Uani 1 1 d . . . . .
C7 C 0.20040(16) 0.1747(2) 0.28438(7) 0.0479(4) Uani 1 1 d . . . . .
H7 H 0.2282 0.2897 0.2678 0.058 Uiso 1 1 calc R . . . .
C6 C 0.17006(18) 0.0231(3) 0.24629(7) 0.0562(4) Uani 1 1 d . . . . .
H6 H 0.1774 0.0361 0.2039 0.067 Uiso 1 1 calc R . . . .
C4 C 0.11692(18) -0.1740(2) 0.33251(8) 0.0518(4) Uani 1 1 d . . . . .
H4 H 0.0896 -0.2908 0.3481 0.062 Uiso 1 1 calc R . . . .
C18 C 0.5306(2) 1.4371(3) 0.68934(8) 0.0604(5) Uani 1 1 d . . . . .
H18A H 0.4502 1.5147 0.6964 0.091 Uiso 1 1 calc GR . . . .
H18B H 0.6058 1.5160 0.6765 0.091 Uiso 1 1 calc GR . . . .
H18C H 0.5600 1.3722 0.7268 0.091 Uiso 1 1 calc GR . . . .
C5 C 0.12816(19) -0.1507(3) 0.27037(8) 0.0579(5) Uani 1 1 d . . . . .
H5 H 0.1076 -0.2520 0.2438 0.069 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 O2 C14 121.90(10) . . ?
C1 N2 H2 116.8 . . ?
C10 N2 H2 116.8 . . ?
C10 N2 C1 126.48(11) . . ?
C1 N1 C8 117.88(11) . . ?
C16 C11 C12 119.13(12) . . ?
C16 C11 C10 123.74(12) . . ?
C12 C11 C10 117.07(12) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 C11 121.03(12) . . ?
C15 C16 H16 119.5 . . ?
N2 C1 C2 121.57(11) . . ?
N1 C1 N2 114.44(11) . . ?
N1 C1 C2 123.93(12) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.55(12) . . ?
C13 C12 H12 119.7 . . ?
N1 C8 C9 122.58(12) . . ?
N1 C8 C7 118.75(12) . . ?
C9 C8 C7 118.66(12) . . ?
C1 C2 H2A 120.8 . . ?
C3 C2 C1 118.30(12) . . ?
C3 C2 H2A 120.8 . . ?
N2 C10 C11 115.96(11) . . ?
O1 C10 N2 123.08(13) . . ?
O1 C10 C11 120.95(12) . . ?
C13 C14 O2 115.14(11) . . ?
C13 C14 C15 121.35(12) . . ?
C15 C14 O2 123.35(12) . . ?
C12 C13 C14 119.37(12) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C9 120.28(12) . . ?
C9 C3 H3 119.9 . . ?
C16 C15 H15 120.7 . . ?
C14 C15 C16 118.52(12) . . ?
C14 C15 H15 120.7 . . ?
C3 C9 C8 117.01(12) . . ?
C4 C9 C8 119.76(13) . . ?
C4 C9 C3 123.22(13) . . ?
O2 C17 C18 110.67(12) . . ?
O3 C17 O2 123.36(13) . . ?
O3 C17 C18 125.96(14) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 C8 120.23(15) . . ?
C6 C7 H7 119.9 . . ?
C7 C6 H6 119.6 . . ?
C7 C6 C5 120.73(15) . . ?
C5 C6 H6 119.6 . . ?
C9 C4 H4 120.1 . . ?
C5 C4 C9 119.74(15) . . ?
C5 C4 H4 120.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.88(15) . . ?
C4 C5 H5 119.6 . . ?
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
O2 C14 1.3957(16) . ?
O2 C17 1.3556(17) . ?
N2 H2 0.8600 . ?
N2 C1 1.4027(16) . ?
N2 C10 1.3681(16) . ?
O1 C10 1.2144(17) . ?
O3 C17 1.1923(17) . ?
N1 C1 1.3142(16) . ?
N1 C8 1.3673(17) . ?
C11 C16 1.3895(18) . ?
C11 C12 1.3922(18) . ?
C11 C10 1.4958(18) . ?
C16 H16 0.9300 . ?
C16 C15 1.3877(19) . ?
C1 C2 1.4181(18) . ?
C12 H12 0.9300 . ?
C12 C13 1.3802(19) . ?
C8 C9 1.4162(19) . ?
C8 C7 1.4167(18) . ?
C2 H2A 0.9300 . ?
C2 C3 1.3584(19) . ?
C14 C13 1.3834(19) . ?
C14 C15 1.3876(18) . ?
C13 H13 0.9300 . ?
C3 H3 0.9300 . ?
C3 C9 1.4158(19) . ?
C15 H15 0.9300 . ?
C9 C4 1.4143(19) . ?
C17 C18 1.484(2) . ?
C7 H7 0.9300 . ?
C7 C6 1.369(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.397(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.367(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C5 H5 0.9300 . ?
