Crystal structure of 2-chloro-3-((thiophen-2-ylmethyl)amino)naphthalene-1,4-dione, C30H20O4N2Cl2S2
Jia, Li-Mei; Luo, Peng; Pan, Wei-Gao; Zeitschrift für Kristallographie - New Crystal Structures 237 (2022) 81–83; doi:10.1515/ncrs-2021-0387

data_8104967
_publ_section_title
;
 Crystal structure of
 2-chloro-3-((thiophen-2-ylmethyl)amino)naphthalene-1,4-dione,
 C30H20O4N2Cl2S2
;
_journal_issue                   1
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              81
_journal_page_last               83
_journal_paper_doi               10.1515/ncrs-2021-0387
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         '2(C15 H10 Cl N O2 S)'
_chemical_formula_sum            'C30 H20 Cl2 N2 O4 S2'
_chemical_formula_weight         607.50
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.9808(14)
_cell_length_b                   7.5227(6)
_cell_length_c                   20.8027(16)
_cell_measurement_reflns_used    9905
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.496
_cell_measurement_theta_min      2.962
_cell_volume                     2657.4(4)
_computing_cell_refinement       'Bruker SAINT[1]'
_computing_data_collection       'Bruker APEX3[1]'
_computing_data_reduction        'Bruker SAINT[1]'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)[2]'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)[2]'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)[7]'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)[3]'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            39478
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         2.962
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.444
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1170 before and 0.0646 after correction.
The Ratio of minimum to maximum transmission is 0.8916.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.12(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         6062
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0642
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1013P)^2^+1.2771P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1584
_refine_ls_wR_factor_ref         0.1809
_reflns_Friedel_coverage         0.944
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                4101
_reflns_number_total             6062
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0387_suppl.cif
_cod_data_source_block           111
_cod_database_code               8104967
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.860
_olex2_refinement_description
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1. Twinned data refinement
 Scales: 0.88(17)
 0.12(17)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
3. Restrained distances
 C28A-C27 \\sim C28B-C27
 with sigma of 0.002
 S2B-C29 \\sim S2A-C30
 with sigma of 0.002
 S2B-C27 \\sim S2A-C27
 with sigma of 0.002
 C30-C28B \\sim C29-C28A
 with sigma of 0.002
4. Rigid bond restraints
 C12
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
5. Uiso/Uaniso restraints and constraints
C12: within 2A with sigma of 0.001 and sigma for terminal atoms of 0.002 within
2A
C27: within 2A with sigma of 0.001 and sigma for terminal atoms of 0.002 within
2A
Uanis(S1B) = Uanis(C13A) = Uanis(C13B) = Uanis(S1A)
Uanis(S2B) = Uanis(C28A) = Uanis(C28B) = Uanis(S2A)
6. Rigid body (RIGU) restrains
 S2A, C27, C28A, C29, C30
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 S2B, C27, C28B, C29, C30
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
7. Others
 Sof(S2A)=Sof(C28A)=Sof(H28A)=Sof(H29A)=Sof(H30A)=1-FVAR(1)
 Sof(S2B)=Sof(H29)=Sof(C28B)=Sof(H28B)=Sof(H30)=FVAR(1)
 Sof(S1B)=Sof(C13B)=Sof(H13B)=Sof(H14A)=Sof(H15A)=1-FVAR(2)
 Sof(S1A)=Sof(C13A)=Sof(H13A)=Sof(H14)=Sof(H15)=FVAR(2)
8.a :
 C28A(C29)
8.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C26(H26A,H26B)
8.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C4(H4), C5(H5), C6(H6), C13A(H13A), C13B(H13B), C14(H14),
 C14(H14A), C15(H15), C15(H15A), N2(H2), C16(H16), C19(H19), C20(H20), C21(H21),
  C28A(H28A), C29(H29), C29(H29A), C28B(H28B), C30(H30), C30(H30A)
8.d Fitted hexagon refined as free rotating group:
 C1(C2,C3,C4,C5,C6), C16(C17,C18,C19,C20,C21)
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