#------------------------------------------------------------------------------
#$Date: 2026-04-05 19:47:32 +0200 (Sun, 05 Apr 2026) $
#$Revision: 305453 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/1/57/70/1577029.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_1577029
_publ_author_name
'C. Biagioni J. Sejkora Y. Moelo A. Criscuolo Z. Dolnicek'
_publ_section_title
;
 When mineralogy meets the organic chemistry: delchiaroite, Cu3I(CH3S)2,
 the first copper iodide-methanethiolate from the Carrara marble quarries,
 Apuan Alps, Tuscany, Italy
;
_journal_name_full               'European Journal of Mineralogy'
_journal_page_first              157
_journal_page_last               163
_journal_paper_doi               10.5194/ejm-38-153-2026
_journal_volume                  38
_journal_year                    2026
_chemical_compound_source        'La Piana quarry, Carrara, Italy'
_chemical_formula_analytical     'C1.92 Cu3.07 H5.76 I1.01 S1.92'
_chemical_formula_sum            'C2 H6 Cu3 I S2'
_chemical_formula_weight         411.74
_chemical_name_mineral           delchiaroite
_space_group_crystal_system      orthorhombic
_space_group_IT_number           59
_space_group_name_Hall           '-P 2ab 2a'
_space_group_name_H-M_alt        'P m m n :2'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.924(10)
_cell_length_b                   4.099(2)
_cell_length_c                   5.572(3)
_cell_measurement_reflns_used    1326
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.28
_cell_measurement_theta_min      2.406
_cell_volume                     386.5(4)
_computing_cell_refinement       'Apex4 (Bruker AXS Inc., 2022)'
_computing_data_collection       'Apex4 (Bruker AXS Inc., 2022)'
_computing_data_reduction        'Apex4 (Bruker AXS Inc., 2022)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1227
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            6453
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.334
_diffrn_reflns_theta_min         2.407
_diffrn_source                   micro-focus
_exptl_absorpt_coefficient_mu    12.606
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    3.538
_exptl_crystal_description       acicular
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.075
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.015
_refine_diff_density_max         6.647
_refine_diff_density_min         -1.976
_refine_diff_density_rms         0.975
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     27
_refine_ls_number_reflns         456
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.156
_refine_ls_R_factor_all          0.1120
_refine_ls_R_factor_gt           0.0962
_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)+(0.1710P)²+2.5999P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2389
_refine_ls_wR_factor_ref         0.2557
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                360
_reflns_number_total             456
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            delchiaroite.cif
_cod_data_source_block           delchiaroite
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_sg_symbol_H-M      'P m m n'
_cod_database_code               1577029
_shelx_shelxl_version_number     2018/1
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, -z'
'-x, y+1/2, -z'
'-x+1/2, -y+1/2, z'
'-x, -y, -z'
'-x-1/2, y, z'
'x, -y-1/2, z'
'x-1/2, y-1/2, -z'
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
I1 I 0.750000 0.750000 0.9846(4) 0.0336(9) Uani 1 4 d S T P . .
Cu1 Cu 0.83561(19) 0.750000 0.5934(6) 0.0390(10) Uani 1 2 d S T P . .
Cu2 Cu 0.750000 0.250000 0.3429(9) 0.0409(13) Uani 1 4 d S T P . .
S S 0.8751(4) 0.250000 0.4880(10) 0.0324(14) Uani 1 2 d S T P . .
C C 0.0598(16) 0.750000 0.767(6) 0.060(9) Uani 1 2 d S T P . .
H1 H 0.087137 0.675648 0.906869 0.090 Uiso 0.5 1 d . U P . .
H2 H 0.015349 0.607112 0.736362 0.090 Uiso 0.5 1 d . U P . .
H3 H 0.039917 0.967240 0.794720 0.090 Uiso 0.5 1 d . U P . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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
Cu1 I1 Cu1 67.24(15) 6_755 .
Cu1 I1 Cu2 125.52(7) 6_755 1_566
Cu1 I1 Cu2 125.52(7) . 1_566
Cu1 I1 Cu2 125.52(7) 6_755 1_556
Cu1 I1 Cu2 125.52(7) . 1_556
Cu2 I1 Cu2 91.50(15) 1_566 1_556
S Cu1 S 133.0(3) 1_565 .
S Cu1 I1 112.62(16) 1_565 .
S Cu1 I1 112.62(16) . .
S Cu1 Cu2 50.86(17) 1_565 1_565
S Cu1 Cu2 132.7(2) . 1_565
I1 Cu1 Cu2 97.21(12) . 1_565
S Cu1 Cu2 132.7(2) 1_565 .
S Cu1 Cu2 50.86(17) . .
I1 Cu1 Cu2 97.21(12) . .
Cu2 Cu1 Cu2 91.06(14) 1_565 .
S Cu1 Cu1 107.42(18) 1_565 6_755
S Cu1 Cu1 107.42(18) . 6_755
I1 Cu1 Cu1 56.38(8) . 6_755
Cu2 Cu1 Cu1 59.70(7) 1_565 6_755
Cu2 Cu1 Cu1 59.70(7) . 6_755
S Cu1 C 104.1(3) 1_565 5_666
S Cu1 C 29.4(3) . 5_666
I1 Cu1 C 141.9(3) . 5_666
Cu2 Cu1 C 114.1(5) 1_565 5_666
Cu2 Cu1 C 62.7(4) . 5_666
Cu1 Cu1 C 121.6(5) 6_755 5_666
S Cu1 C 29.4(3) 1_565 5_676
S Cu1 C 104.1(3) . 5_676
I1 Cu1 C 141.9(3) . 5_676
Cu2 Cu1 C 62.7(4) 1_565 5_676
Cu2 Cu1 C 114.1(5) . 5_676
Cu1 Cu1 C 121.6(5) 6_755 5_676
C Cu1 C 74.8(6) 5_666 5_676
S Cu2 S 138.2(4) 6_755 .
S Cu2 I1 104.41(12) 6_755 1_544
S Cu2 I1 104.41(12) . 1_544
S Cu2 I1 104.41(12) 6_755 1_554
S Cu2 I1 104.41(12) . 1_554
I1 Cu2 I1 91.51(15) 1_544 1_554
S Cu2 Cu1 107.33(18) 6_755 .
S Cu2 Cu1 49.86(9) . .
I1 Cu2 Cu1 148.25(10) 1_544 .
I1 Cu2 Cu1 80.09(7) 1_554 .
S Cu2 Cu1 49.86(9) 6_755 6_755
S Cu2 Cu1 107.33(18) . 6_755
I1 Cu2 Cu1 148.25(10) 1_544 6_755
I1 Cu2 Cu1 80.10(7) 1_554 6_755
Cu1 Cu2 Cu1 60.59(14) . 6_755
S Cu2 Cu1 49.86(9) 6_755 6_745
S Cu2 Cu1 107.33(18) . 6_745
I1 Cu2 Cu1 80.10(7) 1_544 6_745
I1 Cu2 Cu1 148.25(10) 1_554 6_745
Cu1 Cu2 Cu1 121.8(2) . 6_745
Cu1 Cu2 Cu1 91.06(14) 6_755 6_745
S Cu2 Cu1 107.33(18) 6_755 1_545
S Cu2 Cu1 49.86(9) . 1_545
I1 Cu2 Cu1 80.10(7) 1_544 1_545
I1 Cu2 Cu1 148.25(10) 1_554 1_545
Cu1 Cu2 Cu1 91.06(14) . 1_545
Cu1 Cu2 Cu1 121.8(2) 6_755 1_545
Cu1 Cu2 Cu1 60.60(14) 6_745 1_545
S Cu2 C 31.7(6) 6_755 2_566
S Cu2 C 169.9(7) . 2_566
I1 Cu2 C 82.5(4) 1_544 2_566
I1 Cu2 C 82.5(4) 1_554 2_566
Cu1 Cu2 C 125.9(3) . 2_566
Cu1 Cu2 C 66.1(4) 6_755 2_566
Cu1 Cu2 C 66.1(4) 6_745 2_566
Cu1 Cu2 C 125.9(3) 1_545 2_566
S Cu2 C 169.9(7) 6_755 5_666
S Cu2 C 31.7(6) . 5_666
I1 Cu2 C 82.5(4) 1_544 5_666
I1 Cu2 C 82.5(4) 1_554 5_666
Cu1 Cu2 C 66.1(4) . 5_666
Cu1 Cu2 C 125.9(3) 6_755 5_666
Cu1 Cu2 C 125.9(3) 6_745 5_666
Cu1 Cu2 C 66.1(4) 1_545 5_666
C Cu2 C 158.4(12) 2_566 5_666
C S Cu1 113.02(18) 5_666 .
C S Cu1 113.02(18) 5_666 1_545
Cu1 S Cu1 133.0(3) . 1_545
C S Cu2 106.8(11) 5_666 .
Cu1 S Cu2 79.3(2) . .
Cu1 S Cu2 79.3(2) 1_545 .
S C Cu2 41.5(6) 5_666 5_666
S C Cu1 37.6(3) 5_666 5_666
Cu2 C Cu1 51.2(4) 5_666 5_666
S C Cu1 37.6(3) 5_666 5_676
Cu2 C Cu1 51.2(4) 5_666 5_676
Cu1 C Cu1 74.8(6) 5_666 5_676
S C H1 110.4(19) 5_666 .
Cu2 C H1 71.2(14) 5_666 .
Cu1 C H1 92.1(12) 5_666 .
Cu1 C H1 115.2(16) 5_676 .
S C H2 109(2) 5_666 .
Cu2 C H2 136.8(13) 5_666 .
Cu1 C H2 86.2(12) 5_666 .
Cu1 C H2 132(2) 5_676 .
H1 C H2 109.2(18) . .
S C H3 109.8(17) 5_666 .
Cu2 C H3 111.9(14) 5_666 .
Cu1 C H3 147(2) 5_666 .
Cu1 C H3 73.5(12) 5_676 .
H1 C H3 110(3) . .
H2 C H3 108(2) . .
S C H1 110.4(19) 5_666 7_575
Cu2 C H1 71.2(14) 5_666 7_575
Cu1 C H1 115.2(16) 5_666 7_575
Cu1 C H1 92.1(12) 5_676 7_575
H1 C H1 37.3(13) . 7_575
H2 C H1 136(3) . 7_575
H3 C H1 75.3(16) . 7_575
S C H2 109(2) 5_666 7_575
Cu2 C H2 136.8(13) 5_666 7_575
Cu1 C H2 132(2) 5_666 7_575
Cu1 C H2 86.2(12) 5_676 7_575
H1 C H2 136(3) . 7_575
H2 C H2 74(2) . 7_575
H3 C H2 36.7(6) . 7_575
H1 C H2 109.2(18) 7_575 7_575
S C H3 109.8(17) 5_666 7_575
Cu2 C H3 111.9(14) 5_666 7_575
Cu1 C H3 73.5(12) 5_666 7_575
Cu1 C H3 147(2) 5_676 7_575
H1 C H3 75.3(15) . 7_575
H2 C H3 36.7(6) . 7_575
H3 C H3 135(3) . 7_575
H1 C H3 110(3) 7_575 7_575
H2 C H3 108(2) 7_575 7_575
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 Cu1 2.617(4) 6_755
I1 Cu1 2.617(4) .
I1 Cu2 2.861(4) 1_566
I1 Cu2 2.861(4) 1_556
Cu1 S 2.234(3) 1_565
Cu1 S 2.234(3) .
Cu1 Cu2 2.872(3) 1_565
Cu1 Cu2 2.872(3) .
Cu1 Cu1 2.898(7) 6_755
Cu1 C 3.37(2) 5_666
Cu1 C 3.37(2) 5_676
Cu2 S 2.267(7) 6_755
Cu2 S 2.267(7) .
Cu2 C 3.28(3) 2_566
Cu2 C 3.28(3) 5_666
S C 1.80(3) 5_666
C H1 0.95(3) .
C H2 0.97(2) .
C H3 0.964(10) .
C H1 0.95(3) 7_575
C H2 0.97(2) 7_575
C H3 0.964(10) 7_575
