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#$Date: 2023-10-05 10:48:31 +0300 (Thu, 05 Oct 2023) $
#$Revision: 286671 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/75/8107580.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_8107580
loop_
_publ_author_name
'Xiao, Ze-en'
'Wang, Yiqun'
'Cui, Hao'
_publ_section_title
;
 The crystal structure of dimethyl
 4,4′-(10,20-diphenylporphyrin-5,15-diyl)dibenzoate dichloromethane
 solvate, C49H36N4O4Cl2
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              849
_journal_page_last               851
_journal_paper_doi               10.1515/ncrs-2023-0233
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C H2 Cl2, C48 H34 N4 O4'
_chemical_formula_sum            'C49 H34 Cl2 N4 O4'
_chemical_formula_weight         813.70
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_cell_angle_alpha                95.986(3)
_cell_angle_beta                 102.790(3)
_cell_angle_gamma                95.563(3)
_cell_formula_units_Z            1
_cell_length_a                   6.3858(2)
_cell_length_b                   12.6484(4)
_cell_length_c                   12.7115(5)
_cell_measurement_reflns_used    4583
_cell_measurement_temperature    150
_cell_measurement_theta_max      75.8410
_cell_measurement_theta_min      4.6910
_cell_volume                     988.12(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -82.00 -29.00   1.00    1.00    --  -41.14 125.00 -90.00   53
  2  ω    -84.00  23.00   1.00    1.00    --  -41.14   0.00-120.00  107
  3  ω   -115.00 -29.00   1.00    1.00    --  -41.14 -38.00-150.00   86
  4  ω     33.00  84.00   1.00    1.00    --   41.14-125.00-150.00   51
  5  ω      1.00  61.00   1.00    1.00    --   41.14 -99.00  90.00   60
  6  ω     45.00 128.00   1.00    4.00    --  112.00 -61.00  60.00   83
  7  ω     74.00 101.00   1.00    4.00    --  112.00-125.00-180.00   27
  8  ω     71.00  98.00   1.00    4.00    --  112.00 -77.00-180.00   27
  9  ω     41.00 138.00   1.00    4.00    --  112.00 -61.00 -60.00   97
 10  ω    102.00 133.00   1.00    4.00    --  112.00 -45.00 150.00   31
 11  ω     86.00 177.00   1.00    4.00    --  112.00  30.00  30.00   91
 12  ω     39.00  85.00   1.00    4.00    --  112.00 -45.00 150.00   46
 13  ω     86.00 175.00   1.00    4.00    --  112.00  30.00 -30.00   89
 14  ω     79.00 117.00   1.00    4.00    --  112.00-125.00-150.00   38
 15  ω     43.00 117.00   1.00    4.00    --  112.00-125.00   0.00   74
 16  ω     46.00 143.00   1.00    4.00    --  112.00 -15.00   0.00   97
 17  ω     30.00  86.00   1.00    4.00    --  112.00 -94.00 -90.00   56
 18  ω     77.00 104.00   1.00    4.00    --  112.00 -94.00  30.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1809350000
_diffrn_orient_matrix_UB_12      0.0636219000
_diffrn_orient_matrix_UB_13      -0.0384551000
_diffrn_orient_matrix_UB_21      0.1406169000
_diffrn_orient_matrix_UB_22      0.0179880000
_diffrn_orient_matrix_UB_23      0.1171502000
_diffrn_orient_matrix_UB_31      0.0981941000
_diffrn_orient_matrix_UB_32      -0.1042118000
_diffrn_orient_matrix_UB_33      -0.0224865000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6696
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.034
_diffrn_reflns_theta_min         3.541
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.904
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark purple'
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       block
_exptl_crystal_F_000             422
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.572
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         3969
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0603
_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)+(0.0839P)²+0.9324P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1683
_refine_ls_wR_factor_ref         0.1734
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3534
_reflns_number_total             3969
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0233_suppl_001.cif
_cod_data_source_block           6
_cod_database_code               8107580
_chemical_oxdiff_formula         CHON
_chemical_oxdiff_usercomment     BJQ
_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   0.726
_shelx_estimated_absorpt_t_min   0.555
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Restrained distances
 Cl2S-C1S = Cl1S-C1S
 1.72 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Cl2S) \\sim Ueq, Uanis(C1S) \\sim Ueq, Uanis(Cl1S) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: Cl1S(0.5) Cl2S(0.5) C1S(0.5) H1SA(0.5) H1SB(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C1S(H1SA,H1SB)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.994
_oxdiff_exptl_absorpt_empirical_full_min 0.564
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
Cl1S Cl 0.2280(10) 0.0418(4) 0.0932(6) 0.156(3) Uani 0.5 1 d D U P A -1
Cl2S Cl -0.1196(13) -0.0396(3) -0.1003(4) 0.144(3) Uani 0.5 1 d D U P A -1
C1S C -0.0548(18) -0.0027(8) 0.0405(8) 0.087(3) Uani 0.5 1 d D U P A -1
H1SA H -0.096614 -0.064800 0.076165 0.105 Uiso 0.5 1 calc R . P A -1
H1SB H -0.139273 0.055410 0.058419 0.105 Uiso 0.5 1 calc R . P A -1
O1 O 1.2406(3) 0.09384(15) 0.73863(16) 0.0410(5) Uani 1 1 d . . . . .
O2 O 1.0017(3) -0.03542(13) 0.63060(14) 0.0300(4) Uani 1 1 d . . . . .
N1 N 0.1405(3) 0.39761(13) 0.41279(13) 0.0173(4) Uani 1 1 d . . . . .
N2 N 0.2506(3) 0.49635(13) 0.63884(13) 0.0168(3) Uani 1 1 d . . . . .
H2 H 0.150(5) 0.503(2) 0.579(3) 0.036(8) Uiso 1 1 d . . . . .
C23 C -0.3878(4) 0.2172(2) -0.0346(2) 0.0353(6) Uani 1 1 d . . . . .
H23 H -0.522(6) 0.172(3) -0.064(3) 0.051(10) Uiso 1 1 d . . . . .
C1 C 0.4371(3) 0.35769(15) 0.55876(16) 0.0167(4) Uani 1 1 d . . . . .
C2 C 0.3175(3) 0.34798(15) 0.45054(16) 0.0176(4) Uani 1 1 d . . . . .
C21 C -0.0564(4) 0.3066(2) -0.05757(19) 0.0347(6) Uani 1 1 d . . . . .
H21 H 0.055(6) 0.323(3) -0.104(3) 0.047(9) Uiso 1 1 d . . . . .
C22 C -0.2436(5) 0.2366(2) -0.09873(18) 0.0348(6) Uani 1 1 d . . . . .
H22 H -0.270(6) 0.206(3) -0.172(3) 0.054(10) Uiso 1 1 d . . . . .
C3 C 0.3709(3) 0.28119(17) 0.36215(17) 0.0225(4) Uani 1 1 d . . . . .
H3 H 0.488(5) 0.244(2) 0.371(2) 0.025(7) Uiso 1 1 d . . . . .
C24 C -0.3433(4) 0.26741(19) 0.07230(18) 0.0283(5) Uani 1 1 d . . . . .
H24 H -0.443(5) 0.253(2) 0.118(3) 0.035(8) Uiso 1 1 d . . . . .
C4 C 0.2219(3) 0.29022(17) 0.27088(17) 0.0224(4) Uani 1 1 d . . . . .
H4 H 0.217(5) 0.256(2) 0.199(2) 0.032(7) Uiso 1 1 d . . . . .
C20 C -0.0120(4) 0.3574(2) 0.04894(18) 0.0280(5) Uani 1 1 d . . . . .
H20 H 0.124(5) 0.403(2) 0.078(2) 0.030(7) Uiso 1 1 d . . . . .
C5 C 0.0774(3) 0.36203(16) 0.30351(16) 0.0177(4) Uani 1 1 d . . . . .
C19 C -0.1541(3) 0.33699(17) 0.11530(16) 0.0209(4) Uani 1 1 d . . . . .
C6 C -0.1055(3) 0.38726(15) 0.23132(15) 0.0177(4) Uani 1 1 d . . . . .
C7 C 0.4040(3) 0.42735(15) 0.64513(16) 0.0173(4) Uani 1 1 d . . . . .
C8 C 0.5116(3) 0.43411(17) 0.75746(16) 0.0213(4) Uani 1 1 d . . . . .
H8 H 0.627(4) 0.393(2) 0.787(2) 0.023(6) Uiso 1 1 d . . . . .
C9 C 0.4195(3) 0.50505(17) 0.81527(16) 0.0217(4) Uani 1 1 d . . . . .
H9 H 0.450(5) 0.523(2) 0.893(2) 0.031(7) Uiso 1 1 d . . . . .
C10 C 0.2518(3) 0.54427(16) 0.74108(16) 0.0177(4) Uani 1 1 d . . . . .
C11 C 0.6024(3) 0.28253(16) 0.58639(15) 0.0180(4) Uani 1 1 d . . . . .
C12 C 0.5367(3) 0.17207(16) 0.57153(16) 0.0198(4) Uani 1 1 d . . . . .
H12 H 0.387(4) 0.1477(19) 0.541(2) 0.016(6) Uiso 1 1 d . . . . .
C13 C 0.6857(3) 0.10081(16) 0.59960(17) 0.0206(4) Uani 1 1 d . . . . .
H13 H 0.632(4) 0.027(2) 0.588(2) 0.021(6) Uiso 1 1 d . . . . .
C14 C 0.9025(3) 0.13892(16) 0.64362(15) 0.0189(4) Uani 1 1 d . . . . .
C15 C 0.9691(3) 0.24902(17) 0.65898(17) 0.0209(4) Uani 1 1 d . . . . .
H15 H 1.123(4) 0.275(2) 0.691(2) 0.017(6) Uiso 1 1 d . . . . .
C16 C 0.8200(3) 0.31993(16) 0.63030(17) 0.0210(4) Uani 1 1 d . . . . .
H16 H 0.864(4) 0.395(2) 0.640(2) 0.019(6) Uiso 1 1 d . . . . .
C17 C 1.0677(3) 0.06596(17) 0.67762(17) 0.0229(4) Uani 1 1 d . . . . .
C18 C 1.1543(4) -0.1107(2) 0.6585(2) 0.0354(6) Uani 1 1 d . . . . .
H18A H 1.165(5) -0.119(3) 0.733(3) 0.041(8) Uiso 1 1 d . . . . .
H18B H 1.290(6) -0.089(3) 0.645(3) 0.047(9) Uiso 1 1 d . . . . .
H18C H 1.090(6) -0.179(3) 0.608(3) 0.051(9) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
Cl2S C1S Cl1S 112.3(6) . .
C17 O2 C18 115.42(19) . .
C2 N1 C5 105.26(16) . .
C7 N2 C10 110.02(16) . .
C22 C23 C24 119.9(2) . .
C2 C1 C11 117.84(17) . .
C7 C1 C2 125.13(18) . .
C7 C1 C11 116.88(17) . .
N1 C2 C1 126.43(18) . .
N1 C2 C3 110.75(17) . .
C1 C2 C3 122.81(18) . .
C22 C21 C20 120.1(2) . .
C23 C22 C21 120.1(2) . .
C4 C3 C2 106.61(18) . .
C19 C24 C23 120.7(2) . .
C3 C4 C5 106.32(18) . .
C19 C20 C21 120.4(2) . .
N1 C5 C4 111.03(17) . .
N1 C5 C6 125.82(18) . .
C6 C5 C4 123.12(18) . .
C24 C19 C20 118.8(2) . .
C24 C19 C6 119.9(2) . .
C20 C19 C6 121.31(19) . .
C5 C6 C19 118.31(18) . .
C5 C6 C10 125.39(18) . 2_566
C10 C6 C19 116.29(17) 2_566 .
N2 C7 C1 126.17(17) . .
N2 C7 C8 106.92(17) . .
C1 C7 C8 126.75(18) . .
C9 C8 C7 108.01(18) . .
C8 C9 C10 108.18(18) . .
N2 C10 C6 126.72(18) . 2_566
N2 C10 C9 106.86(17) . .
C6 C10 C9 126.27(19) 2_566 .
C12 C11 C1 119.51(17) . .
C16 C11 C1 121.58(18) . .
C16 C11 C12 118.87(18) . .
C13 C12 C11 120.69(18) . .
C12 C13 C14 120.03(19) . .
C13 C14 C15 119.59(18) . .
C13 C14 C17 122.09(19) . .
C15 C14 C17 118.31(18) . .
C16 C15 C14 120.22(18) . .
C15 C16 C11 120.60(19) . .
O1 C17 O2 123.4(2) . .
O1 C17 C14 124.4(2) . .
O2 C17 C14 112.15(18) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1S C1S 1.793(12) .
Cl2S C1S 1.748(11) .
O1 C17 1.197(3) .
O2 C17 1.343(3) .
O2 C18 1.442(3) .
N1 C2 1.365(2) .
N1 C5 1.371(3) .
N2 C7 1.369(3) .
N2 C10 1.374(3) .
C23 C22 1.380(4) .
C23 C24 1.394(3) .
C1 C2 1.404(3) .
C1 C7 1.401(3) .
C1 C11 1.497(3) .
C2 C3 1.456(3) .
C21 C22 1.381(4) .
C21 C20 1.393(3) .
C3 C4 1.351(3) .
C24 C19 1.390(3) .
C4 C5 1.450(3) .
C20 C19 1.393(3) .
C5 C6 1.402(3) .
C19 C6 1.496(3) .
C6 C10 1.409(3) 2_566
C7 C8 1.431(3) .
C8 C9 1.359(3) .
C9 C10 1.427(3) .
C11 C12 1.400(3) .
C11 C16 1.393(3) .
C12 C13 1.388(3) .
C13 C14 1.391(3) .
C14 C15 1.396(3) .
C14 C17 1.490(3) .
C15 C16 1.387(3) .
