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_1573810
_publ_section_title
;
 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         'C70 H71.533 O4 P2'
_chemical_formula_sum            'C70 H71.53 O4 P2'
_chemical_formula_weight         1038.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-03
_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                90
_cell_angle_beta                 97.3440(10)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   58.8812(19)
_cell_length_b                   8.3047(3)
_cell_length_c                   34.7288(11)
_cell_measurement_reflns_used    9415
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.48
_cell_volume                     16842.7(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)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0458
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       78
_diffrn_reflns_limit_h_min       -78
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            111020
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         2.092
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6857
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0671 before and 0.0549 after correction.
The Ratio of minimum to maximum transmission is 0.9197.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       block
_exptl_crystal_F_000             6642
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.025
_refine_diff_density_max         1.142
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1158
_refine_ls_number_reflns         20858
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0774
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0679P)^2^+49.3638P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1799
_refine_ls_wR_factor_ref         0.1883
_reflns_Friedel_coverage         0.000
_reflns_number_gt                17370
_reflns_number_total             20858
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc07106a2.cif
_cod_data_source_block           '_bc10_abc_a'
_cod_depositor_comments
'Adding full bibliography for 1573806--1573810.cif.'
_cod_database_code               1573810
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.975
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H02,HB,HC} of C02N, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  {H9A,H9B,H9C} of C9, {H8A,H8B,H8C} of C8, {H1A,H1B,H1C} of C1, {HP,H7,HQ}
  of C02U, {H3A,H3B,H3C} of C3
2. Restrained distances
 C02Z-C2 \\sim C02Z-C2A
 with sigma of 0.02
 C2-C4 \\sim C2A-C4
 with sigma of 0.02
3. Others
 Fixed Sof: H02S(0.15) H02T(0.15) H02R(0.85) H02Q(0.85) H02U(0.85) H02V(0.85)
 C02M(0.85) H02Z(0.85) HA(0.85) H02(0.15) HB(0.85) HC(0.85) HE(0.6) HF(0.6)
 H2(0.4) HG(0.4) H3(0.85) HH(0.85) HI(0.15) HJ(0.15) C02R(0.85) H4(0.85)
 HK(0.85) HM(0.15) HN(0.15) H6(0.85) HO(0.85) C02V(0.85) H8(0.85) HR(0.85)
 C02W(0.8) H9(0.8) HS(0.8) C02Y(0.85) H10(0.85) HT(0.85) C02Z(0.6) H11(0.6)
 HU(0.6) H030(0.6) C032(0.7) H03A(0.7) H03B(0.7) C2(0.5) H2A(0.5) H2B(0.5)
 C4(0.4) H4A(0.4) H4B(0.4) C7(0.75) H7A(0.75) H7B(0.75) C2A(0.5) H2AB(0.5)
 H2AA(0.5) C22(0.2) C83(0.15) H83A(0.15) H83B(0.15) C3(0.7) H3A(0.7) H3B(0.7)
 H3C(0.7) C1(0.6) H1A(0.6) H1B(0.6) H1C(0.6) C18(0.15) H18A(0.15) H18B(0.15)
 C23(0.15) H23A(0.15) H23B(0.15) C30(0.15) H30A(0.15) H30B(0.15) C41(0.15)
 C5(0.4) H5A(0.4) H5B(0.4) C8(0.3) H8A(0.3) H8B(0.3) H8C(0.3) C9(0.4) H9A(0.4)
 H9B(0.4) H9C(0.4) C10(0.55) H10A(0.55) H10B(0.55) C11(0.5) H11A(0.5) H11B(0.5)
 C12(0.45) H12A(0.45) H12B(0.45) C14(0.5) C6(0.85) H6B(0.85) H6A(0.85)
 C13(0.15) H13(0.15)
4.a Secondary CH2 refined with riding coordinates:
 C00X(H00A,H00B), C01D(H01A,H01D), C01P(H01E,H01P), C01Q(H01Q,H01R), C024(H02A,
 H02B), C028(H02C,H02D), C029(H02E,H02F), C02B(H02H,H02I), C02F(H02M,H02N),
 C02G(H02P,H02O), C02H(H02S,H02T), C02H(H02R,H02Q), C02I(H02U,H02V), C02J(H02X,
 H02W), C02L(H,H02Y), C02M(H02Z,HA), C02N(HB,HC), C02O(HD,H1), C02P(HE,HF),
 C02P(H2,HG), C02Q(H3,HH), C02Q(HI,HJ), C02R(H4,HK), C02S(HL,H5), C02T(HM,HN),
 C02T(H6,HO), C02V(H8,HR), C02W(H9,HS), C02Y(H10,HT), C02Z(H11,HU), C032(H03A,
 H03B), C2(H2A,H2B), C4(H4A,H4B), C7(H7A,H7B), C2A(H2AB,H2AA), C83(H83A,H83B),
 C18(H18A,H18B), C23(H23A,H23B), C30(H30A,H30B), C5(H5A,H5B), C10(H10A,H10B),
 C11(H11A,H11B), C12(H12A,H12B), C6(H6B,H6A)
4.b Aromatic/amide H refined with riding coordinates:
 C00R(H00R), C00T(H00T), C00V(H00V), C015(H015), C01B(H01B), C01C(H01C),
 C01F(H01F), C01G(H01G), C01H(H01H), C01I(H01I), C01J(H01J), C01K(H01K),
 C01L(H01L), C01M(H01M), C01N(H01N), C01O(H01O), C01R(H01S), C01S(H01T),
 C01T(H01U), C01U(H01V), C01V(H01W), C01W(H01X), C01X(H01Y), C01Y(H01Z),
 C01Z(H01), C020(H020), C021(H021), C022(H022), C023(H023), C025(H025),
 C026(H026), C027(H027), C02A(H02G), C02C(H02J), C02D(H02K), C02E(H02L),
 C02N(H02), C030(H030), C13(H13)
4.c Idealised Me refined as rotating group:
 C02U(HP,H7,HQ), C3(H3A,H3B,H3C), C1(H1A,H1B,H1C), C8(H8A,H8B,H8C), C9(H9A,H9B,
 H9C)
;
_shelx_res_checksum              53008
_shelx_hkl_checksum              84030
_olex2_submission_special_instructions 'No special instructions were received'