#------------------------------------------------------------------------------
#$Date: 2023-08-31 04:19:16 +0300 (Thu, 31 Aug 2023) $
#$Revision: 285922 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/72/7247274.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_7247274
loop_
_publ_author_name
'Verma, Ekta'
'Patil, Shailendra'
'Gajbhiye, Asmita'
_publ_section_title
;
 Sequential analysis for identification of byproduct from N-benzylation
 reaction: wound healing and anti-inflammatory potential of the byproduct
 4-chlorobenzyl 2-((4-chlorobenzyl)amino)benzoate
;
_journal_issue                   37
_journal_name_full               'RSC Advances'
_journal_page_first              25904
_journal_page_last               25911
_journal_paper_doi               10.1039/D3RA03720G
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C21 H17 Cl2 N O2'
_chemical_formula_sum            'C21 H17 Cl2 N O2'
_chemical_formula_weight         386.26
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-01-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-06-03 deposited with the CCDC.	2023-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.272(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.168(8)
_cell_length_b                   5.683(3)
_cell_length_c                   21.306(11)
_cell_measurement_reflns_used    902
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.56
_cell_measurement_theta_min      4.02
_cell_volume                     1807.1(16)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.950
_diffrn_measured_fraction_theta_max 0.890
_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  0.0496
_diffrn_reflns_av_unetI/netI     0.0887
_diffrn_reflns_Laue_measured_fraction_full 0.950
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7043
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.138
_diffrn_reflns_theta_min         4.017
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.375
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'color less'
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_description       plate
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.897
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4330
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.897
_refine_ls_R_factor_all          0.1098
_refine_ls_R_factor_gt           0.0598
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.1000P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1454
_refine_ls_wR_factor_ref         0.1803
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2524
_reflns_number_total             4330
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ra03720g2.cif
_cod_data_source_block           m
_cod_database_code               7247274
_shelxl_version_number           2012-9
_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_max   0.929
_shelx_estimated_absorpt_t_min   0.877
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C17(H17), C18(H18), C20(H20), C21(H21)
;
_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
Cl1 Cl 1.06865(5) 1.28309(17) 0.40217(4) 0.0405(3) Uani 1 1 d . . . . .
Cl2 Cl 0.08009(6) -0.10344(17) 0.23888(4) 0.0435(3) Uani 1 1 d . . . . .
O1 O 0.70688(13) 0.6202(4) 0.41136(10) 0.0304(5) Uani 1 1 d . . . . .
O2 O 0.59184(14) 0.5528(4) 0.46207(10) 0.0330(5) Uani 1 1 d . . . . .
N1 N 0.48183(17) 0.1858(5) 0.41860(13) 0.0285(6) Uani 1 1 d . . . . .
H1 H 0.493(2) 0.294(6) 0.4431(17) 0.033(10) Uiso 1 1 d . . . . .
C1 C 0.9712(2) 1.1425(6) 0.41639(15) 0.0299(7) Uani 1 1 d . . . . .
C2 C 0.9449(2) 0.9346(6) 0.38555(16) 0.0346(8) Uani 1 1 d . . . . .
H2 H 0.9781 0.8690 0.3572 0.042 Uiso 1 1 calc R . . . .
C3 C 0.8678(2) 0.8247(6) 0.39751(15) 0.0327(7) Uani 1 1 d . . . . .
H3 H 0.8495 0.6837 0.3771 0.039 Uiso 1 1 calc R . . . .
C4 C 0.8178(2) 0.9219(5) 0.43935(14) 0.0262(7) Uani 1 1 d . . . . .
C5 C 0.8459(2) 1.1329(6) 0.46929(15) 0.0319(7) Uani 1 1 d . . . . .
H5 H 0.8127 1.1999 0.4974 0.038 Uiso 1 1 calc R . . . .
C6 C 0.9223(2) 1.2445(6) 0.45801(16) 0.0338(8) Uani 1 1 d . . . . .
H6 H 0.9407 1.3861 0.4781 0.041 Uiso 1 1 calc R . . . .
C7 C 0.7346(2) 0.8093(6) 0.45538(16) 0.0304(7) Uani 1 1 d . . . . .
H7A H 0.7468 0.7490 0.4987 0.037 Uiso 1 1 calc R . . . .
H7B H 0.6871 0.9253 0.4525 0.037 Uiso 1 1 calc R . . . .
C8 C 0.63241(19) 0.5035(5) 0.41910(14) 0.0249(6) Uani 1 1 d . . . . .
C9 C 0.60883(19) 0.3153(5) 0.37172(14) 0.0243(6) Uani 1 1 d . . . . .
C10 C 0.6614(2) 0.2832(6) 0.32405(15) 0.0286(7) Uani 1 1 d . . . . .
H10 H 0.7079 0.3877 0.3218 0.034 Uiso 1 1 calc R . . . .
C11 C 0.6459(2) 0.1015(6) 0.28069(16) 0.0334(8) Uani 1 1 d . . . . .
H11 H 0.6804 0.0853 0.2490 0.040 Uiso 1 1 calc R . . . .
C12 C 0.5775(2) -0.0574(6) 0.28524(15) 0.0305(7) Uani 1 1 d . . . . .
H12 H 0.5674 -0.1834 0.2570 0.037 Uiso 1 1 calc R . . . .
C13 C 0.5245(2) -0.0305(5) 0.33111(14) 0.0263(7) Uani 1 1 d . . . . .
H13 H 0.4790 -0.1387 0.3330 0.032 Uiso 1 1 calc R . . . .
C14 C 0.53744(18) 0.1564(5) 0.37494(13) 0.0228(6) Uani 1 1 d . . . . .
C15 C 0.42055(19) 0.0043(6) 0.43213(14) 0.0282(7) Uani 1 1 d . . . . .
H15A H 0.4049 0.0360 0.4735 0.034 Uiso 1 1 calc R . . . .
H15B H 0.4515 -0.1458 0.4350 0.034 Uiso 1 1 calc R . . . .
C16 C 0.3352(2) -0.0171(5) 0.38362(14) 0.0258(7) Uani 1 1 d . . . . .
C17 C 0.2813(2) -0.2161(6) 0.38407(16) 0.0312(7) Uani 1 1 d . . . . .
H17 H 0.2985 -0.3331 0.4143 0.037 Uiso 1 1 calc R . . . .
C18 C 0.2025(2) -0.2421(6) 0.34016(16) 0.0322(8) Uani 1 1 d . . . . .
H18 H 0.1671 -0.3753 0.3409 0.039 Uiso 1 1 calc R . . . .
C19 C 0.1772(2) -0.0674(6) 0.29515(15) 0.0301(7) Uani 1 1 d . . . . .
C20 C 0.2286(2) 0.1307(6) 0.29382(16) 0.0313(7) Uani 1 1 d . . . . .
H20 H 0.2111 0.2470 0.2634 0.038 Uiso 1 1 calc R . . . .
C21 C 0.3068(2) 0.1558(5) 0.33815(14) 0.0278(7) Uani 1 1 d . . . . .
H21 H 0.3411 0.2911 0.3375 0.033 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'
Cl Cl 0.1484 0.1585 '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
C8 O1 C7 116.2(2) . . ?
C14 N1 C15 122.7(3) . . ?
C2 C1 Cl1 119.3(2) . . ?
C2 C1 C6 121.6(3) . . ?
C6 C1 Cl1 119.0(2) . . ?
C1 C2 C3 118.7(3) . . ?
C4 C3 C2 121.0(3) . . ?
C3 C4 C5 118.8(3) . . ?
C3 C4 C7 123.6(3) . . ?
C5 C4 C7 117.6(3) . . ?
C6 C5 C4 121.0(3) . . ?
C5 C6 C1 118.8(3) . . ?
O1 C7 C4 109.1(2) . . ?
O1 C8 C9 112.4(2) . . ?
O2 C8 O1 121.6(3) . . ?
O2 C8 C9 125.9(3) . . ?
C10 C9 C8 119.3(3) . . ?
C10 C9 C14 119.1(3) . . ?
C14 C9 C8 121.6(3) . . ?
C11 C10 C9 121.9(3) . . ?
C10 C11 C12 118.7(3) . . ?
C13 C12 C11 120.9(3) . . ?
C12 C13 C14 121.6(3) . . ?
N1 C14 C9 121.4(3) . . ?
N1 C14 C13 120.8(3) . . ?
C13 C14 C9 117.8(3) . . ?
N1 C15 C16 115.0(3) . . ?
C17 C16 C15 119.5(3) . . ?
C21 C16 C15 122.7(3) . . ?
C21 C16 C17 117.9(3) . . ?
C18 C17 C16 121.1(3) . . ?
C19 C18 C17 119.3(3) . . ?
C18 C19 Cl2 119.3(2) . . ?
C20 C19 Cl2 119.8(3) . . ?
C20 C19 C18 120.9(3) . . ?
C19 C20 C21 119.4(3) . . ?
C20 C21 C16 121.5(3) . . ?
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
Cl1 C1 1.754(3) . ?
Cl2 C19 1.737(3) . ?
O1 C7 1.439(4) . ?
O1 C8 1.345(3) . ?
O2 C8 1.223(3) . ?
N1 C14 1.373(4) . ?
N1 C15 1.451(4) . ?
C1 C2 1.376(4) . ?
C1 C6 1.380(4) . ?
C2 C3 1.389(4) . ?
C3 C4 1.384(4) . ?
C4 C5 1.389(4) . ?
C4 C7 1.508(4) . ?
C5 C6 1.380(4) . ?
C8 C9 1.470(4) . ?
C9 C10 1.411(4) . ?
C9 C14 1.421(4) . ?
C10 C11 1.377(4) . ?
C11 C12 1.392(4) . ?
C12 C13 1.380(4) . ?
C13 C14 1.404(4) . ?
C15 C16 1.511(4) . ?
C16 C17 1.396(4) . ?
C16 C21 1.393(4) . ?
C17 C18 1.388(5) . ?
C18 C19 1.386(4) . ?
C19 C20 1.373(4) . ?
C20 C21 1.386(4) . ?
