From flat to twisted - multifunctional phosphacyclic nanocarbons based on Vat Orange 3.
Dadgaryeganeh, Reza; LeBlanc, Jesse; Pradhan, Ekadashi; Miao, Dandan; Hussein, Amaar; Hunter, Howard N.; Zeng, Tao; Romero-Nieto, Carlos; Baumgartner, Thomas; Chemical science 16 (2025) 3680–3692; doi:10.1039/d4sc07106a

data_1573807
_publ_section_title
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 From flat to twisted - multifunctional phosphacyclic nanocarbons based on
 Vat Orange 3.
;
_journal_issue                   8
_journal_name_full               'Chemical science'
_journal_page_first              3680
_journal_page_last               3692
_journal_paper_doi               10.1039/d4sc07106a
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         '2(C H Cl3), C70 H74 O4 P2'
_chemical_formula_sum            'C72 H76 Cl6 O4 P2'
_chemical_formula_weight         1279.96
_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   geom
_audit_creation_date             2024-06-27
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-07-12 deposited with the CCDC.	2025-01-08 downloaded from the CCDC.
;
_cell_angle_alpha                92.6920(10)
_cell_angle_beta                 93.0840(10)
_cell_angle_gamma                108.4490(10)
_cell_formula_units_Z            1
_cell_length_a                   8.2286(3)
_cell_length_b                   11.7231(4)
_cell_length_c                   17.5716(6)
_cell_measurement_reflns_used    9857
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      30.39
_cell_measurement_theta_min      2.33
_cell_volume                     1601.93(10)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            60577
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.553
_diffrn_reflns_theta_min         2.106
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.368
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6449
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1196 before and 0.0583 after correction.
The Ratio of minimum to maximum transmission is 0.8649.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     446
_refine_ls_number_reflns         7386
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0436
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0356P)^2^+0.9717P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1061
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5966
_reflns_number_total             7386
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07106a2.cif
_cod_data_source_block           5_10_chcl3_0m
_cod_depositor_comments
'Adding full bibliography for 1573806--1573810.cif.'
_cod_database_code               1573807
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.898
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C2-C3 \\sim C2A-C3A
 with sigma of 0.02
 C3-C4 \\sim C3A-C4
 with sigma of 0.02
 C2-C4 \\sim C2A-C4
 with sigma of 0.04
 Cl1-C1 \\sim Cl1A-C1
 with sigma of 0.02
 Cl2-C1 \\sim Cl2A-C1
 with sigma of 0.02
 Cl3-C1 \\sim Cl3A-C1
 with sigma of 0.02
3. Others
 Sof(H1B)=Sof(Cl1A)=Sof(Cl2A)=Sof(Cl3A)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=Sof(H1A)=FVAR(1)
 Fixed Sof: C2(0.6) H2A(0.6) H2B(0.6) H2C(0.6) C3(0.7) H3A(0.7) H3B(0.7)
 H4AA(0.7) H4AB(0.7) H4BC(0.3) H4BD(0.3) C3A(0.15) H3AA(0.15) H3AB(0.15)
 C2A(0.25) H2AA(0.25) H2AB(0.25) H2AC(0.25) C37(0.15) H37A(0.15) H37B(0.15)
 C38(0.15) H38A(0.15) H38B(0.15) H38C(0.15)
4.a Ternary CH refined with riding coordinates:
 C1(H1A), C1(H1B)
4.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4AA,H4AB), C4(H4BC,H4BD), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,
 H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
  C13(H13A,H13B), C3A(H3AA,H3AB), C37(H37A,H37B)
4.c Aromatic/amide H refined with riding coordinates:
 C23(H23), C24(H24), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31),
 C32(H32), C33(H33), C34(H34), C35(H35), C36(H36)
4.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C2A(H2AA,H2AB,H2AC), C38(H38A,H38B,H38C)
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_shelx_res_checksum              67625
_shelx_hkl_checksum              19317
_olex2_submission_special_instructions 'No special instructions were received'