An unexpected chlorination of an organic sunscreen
Smith, Lydia G.; Di Leva, Dalila; Shaw, Lloyd A.; Hughes, Eric; Kenwright, Alan M.; Beeby, Andrew; Wilson, Mark R.; Mahon, Clare S.; Chemical Communications 61 (2025) 9314–9317; doi:10.1039/D5CC01593F

data_7134571
_publ_section_title
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 An unexpected chlorination of an organic sunscreen
;
_journal_issue                   51
_journal_name_full               'Chemical Communications'
_journal_page_first              9314
_journal_page_last               9317
_journal_paper_doi               10.1039/D5CC01593F
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C22 H27 N O4'
_chemical_formula_sum            'C22 H27 N O4'
_chemical_formula_weight         369.464
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_audit_creation_date             2024-12-18
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-12-18 deposited with the CCDC.	2025-05-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9888(3)
_cell_length_b                   9.7763(4)
_cell_length_c                   26.1295(10)
_cell_measurement_reflns_used    9822
_cell_measurement_temperature    120.00
_cell_measurement_theta_max      31.93
_cell_measurement_theta_min      2.22
_cell_volume                     2040.74(14)
_computing_cell_refinement       'SAINT v8.40A (Bruker AXS, 2019)'
_computing_data_collection       'APEX4 v.2022.10_0 (Bruker AXS, 2022)'
_computing_data_reduction        'SAINT v8.40A (Bruker AXS, 2019)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-beta (Bourhis et al., 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.00
_diffrn_detector_area_resol_mean 54.4
_diffrn_detector_type            'CPA sensor'
_diffrn_measured_fraction_theta_full 0.9925
_diffrn_measured_fraction_theta_max 0.9957
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  '3-circle diffractometer'
_diffrn_measurement_method       '\w- and \f-scan'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.9925
_diffrn_reflns_Laue_measured_fraction_max 0.9957
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            59703
_diffrn_reflns_point_group_measured_fraction_full 0.9946
_diffrn_reflns_point_group_measured_fraction_max 0.9969
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         31.00
_diffrn_reflns_theta_min         2.22
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.7046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0773 before and 0.0536 after correction.
The Ratio of minimum to maximum transmission is 0.9439.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'dull light yellow'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_description       block
_exptl_crystal_F_000             792.514
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.2994
_refine_diff_density_min         -0.2424
_refine_diff_density_rms         0.0445
_refine_ls_abs_structure_details
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_d_res_high            0.6901
_refine_ls_d_res_low             9.1564
_refine_ls_goodness_of_fit_ref   1.0409
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    42
_refine_ls_number_parameters     248
_refine_ls_number_reflns         6495
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0409
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0479P)^2^+0.5208P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1054
_reflns_Friedel_coverage         0.999
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              37
_reflns_limit_l_min              -37
_reflns_number_gt                6057
_reflns_number_total             6495
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d5cc01593f3.cif
_cod_data_source_block           23srv199
_cod_depositor_comments
'Adding full bibliography for 7134571--7134572.cif.'
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               7134571
_computing_bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15a,H15b), C17(H17a,H17b), C19(H19a,H19b), C21(H21a,H21b)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c), C18(H18a,H18b,H18c), C20(H20a,H20b,H20c), C22(H22a,H22b,
 H22c)
;
_olex2_submission_original_sample_id
'ethyl 2-(4-(diethylamino)-2-ethoxybenzoyl)benzoate '
_olex2_submission_special_instructions 'No special instructions were received'