#------------------------------------------------------------------------------
#$Date: 2024-12-06 18:36:47 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296385 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/26/1572698.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_1572698
loop_
_publ_author_name
'Pan, Xiuhong'
'Lan, Linfeng'
'Zhang, Hongyu'
_publ_section_title
;
 Flexible organic crystals with multi-stimuli-responsive CPL for broadband
 multicolor optical waveguides.
;
_journal_issue                   42
_journal_name_full               'Chemical science'
_journal_page_first              17444
_journal_page_last               17452
_journal_paper_doi               10.1039/d4sc05005c
_journal_volume                  15
_journal_year                    2024
_chemical_absolute_configuration s
_chemical_formula_moiety         'C16 H17 N O'
_chemical_formula_sum            'C16 H17 N O'
_chemical_formula_weight         239.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2021-06-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_audit_update_record
;
2024-07-25 deposited with the CCDC.	2024-09-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 128.517(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.0857(12)
_cell_length_b                   5.8189(4)
_cell_length_c                   14.3076(9)
_cell_measurement_reflns_used    9149
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.59
_cell_measurement_theta_min      3.95
_cell_volume                     1308.39(15)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11489
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.586
_diffrn_reflns_theta_min         3.949
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.589
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_description       needle
_exptl_crystal_F_000             512
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 1066 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2639
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0401
_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)+(0.0423P)²+0.4572P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1005
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                2489
_reflns_number_total             2639
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc05005c3.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 1572697--1572698.cif.'
_cod_database_code               1572698
_shelx_shelxl_version_number     2014/7
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C12(H12), C13(H13), C15(H15)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C16(H16A,H16B,H16C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, 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
C1 C 0.63308(14) 0.6416(4) 0.8391(2) 0.0314(5) Uani 1 1 d . . . . .
H1 H 0.6352 0.6765 0.7761 0.038 Uiso 1 1 calc R . . . .
C2 C 0.66980(14) 0.7910(4) 0.9352(2) 0.0353(5) Uani 1 1 d . . . . .
H2 H 0.6977 0.9259 0.9380 0.042 Uiso 1 1 calc R . . . .
C3 C 0.66625(14) 0.7455(4) 1.0269(2) 0.0369(5) Uani 1 1 d . . . . .
H3 H 0.6904 0.8499 1.0917 0.044 Uiso 1 1 calc R . . . .
C4 C 0.62689(16) 0.5450(4) 1.0232(2) 0.0370(5) Uani 1 1 d . . . . .
H4 H 0.6247 0.5112 1.0862 0.044 Uiso 1 1 calc R . . . .
C5 C 0.59084(14) 0.3940(4) 0.9278(2) 0.0326(5) Uani 1 1 d . . . . .
H5 H 0.5644 0.2572 0.9263 0.039 Uiso 1 1 calc R . . . .
C6 C 0.59301(13) 0.4404(4) 0.8343(2) 0.0286(5) Uani 1 1 d . . . . .
C7 C 0.54924(13) 0.2809(4) 0.72703(19) 0.0292(5) Uani 1 1 d . . . . .
H7 H 0.5296 0.1404 0.7437 0.035 Uiso 1 1 calc R . . . .
C8 C 0.60546(15) 0.2086(4) 0.6950(2) 0.0350(5) Uani 1 1 d . . . . .
H8A H 0.5747 0.0985 0.6288 0.053 Uiso 1 1 calc GR . . . .
H8B H 0.6574 0.1365 0.7645 0.053 Uiso 1 1 calc GR . . . .
H8C H 0.6206 0.3440 0.6711 0.053 Uiso 1 1 calc GR . . . .
C9 C 0.40123(14) 0.3083(4) 0.5680(2) 0.0282(4) Uani 1 1 d . . . . .
H9 H 0.3966 0.1634 0.5941 0.034 Uiso 1 1 calc R . . . .
C10 C 0.32455(13) 0.4187(4) 0.46464(19) 0.0266(4) Uani 1 1 d . . . . .
C11 C 0.32810(14) 0.6338(4) 0.4229(2) 0.0287(4) Uani 1 1 d . . . . .
C12 C 0.25360(14) 0.7287(4) 0.3217(2) 0.0320(5) Uani 1 1 d . . . . .
H12 H 0.2552 0.8735 0.2925 0.038 Uiso 1 1 calc R . . . .
C13 C 0.17699(14) 0.6120(4) 0.2636(2) 0.0317(5) Uani 1 1 d . . . . .
H13 H 0.1268 0.6792 0.1947 0.038 Uiso 1 1 calc R . . . .
C14 C 0.17139(14) 0.3987(4) 0.3033(2) 0.0302(5) Uani 1 1 d . . . . .
C15 C 0.24598(13) 0.3062(4) 0.4041(2) 0.0284(5) Uani 1 1 d . . . . .
H15 H 0.2438 0.1620 0.4332 0.034 Uiso 1 1 calc R . . . .
C16 C 0.08765(14) 0.2742(4) 0.2395(2) 0.0374(5) Uani 1 1 d . . . . .
H16A H 0.0970 0.1085 0.2408 0.056 Uiso 1 1 calc GR . . . .
H16B H 0.0484 0.3273 0.1565 0.056 Uiso 1 1 calc GR . . . .
H16C H 0.0631 0.3058 0.2797 0.056 Uiso 1 1 calc GR . . . .
N1 N 0.47465(11) 0.4025(3) 0.62424(16) 0.0295(4) Uani 1 1 d . . . . .
O1 O 0.40225(10) 0.7491(3) 0.47669(15) 0.0352(4) Uani 1 1 d . . . . .
H1A H 0.445(2) 0.654(7) 0.539(3) 0.061(10) 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'
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
_geom_angle_publ_flag
C2 C1 H1 119.7 . . ?
C2 C1 C6 120.5(2) . . ?
C6 C1 H1 119.7 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.7(2) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.2(2) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.9(2) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C7 121.0(2) . . ?
C5 C6 C1 118.4(2) . . ?
C5 C6 C7 120.50(19) . . ?
C6 C7 H7 108.9 . . ?
C8 C7 C6 113.74(18) . . ?
C8 C7 H7 108.9 . . ?
N1 C7 C6 107.72(17) . . ?
N1 C7 H7 108.9 . . ?
N1 C7 C8 108.51(18) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 H9 119.2 . . ?
N1 C9 H9 119.2 . . ?
N1 C9 C10 121.5(2) . . ?
C11 C10 C9 121.34(19) . . ?
C15 C10 C9 119.44(19) . . ?
C15 C10 C11 119.2(2) . . ?
C12 C11 C10 119.20(19) . . ?
O1 C11 C10 121.87(19) . . ?
O1 C11 C12 118.91(19) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.1(2) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 119.0 . . ?
C12 C13 C14 122.0(2) . . ?
C14 C13 H13 119.0 . . ?
C13 C14 C16 121.5(2) . . ?
C15 C14 C13 117.3(2) . . ?
C15 C14 C16 121.2(2) . . ?
C10 C15 H15 118.9 . . ?
C14 C15 C10 122.2(2) . . ?
C14 C15 H15 118.9 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C9 N1 C7 118.60(18) . . ?
C11 O1 H1A 106(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9500 . ?
C1 C2 1.388(3) . ?
C1 C6 1.398(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(3) . ?
C6 C7 1.519(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.519(3) . ?
C7 N1 1.471(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9 0.9500 . ?
C9 C10 1.461(3) . ?
C9 N1 1.283(3) . ?
C10 C11 1.408(3) . ?
C10 C15 1.402(3) . ?
C11 C12 1.394(3) . ?
C11 O1 1.354(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.398(3) . ?
C14 C15 1.387(3) . ?
C14 C16 1.508(3) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
O1 H1A 0.94(4) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 1.4(3) . . . . ?
C1 C6 C7 C8 52.9(3) . . . . ?
C1 C6 C7 N1 -67.4(2) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C2 C1 C6 C7 177.29(19) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C4 C5 C6 C7 -176.6(2) . . . . ?
C5 C6 C7 C8 -129.9(2) . . . . ?
C5 C6 C7 N1 109.8(2) . . . . ?
C6 C1 C2 C3 -1.1(3) . . . . ?
C6 C7 N1 C9 -123.81(19) . . . . ?
C8 C7 N1 C9 112.6(2) . . . . ?
C9 C10 C11 C12 178.0(2) . . . . ?
C9 C10 C11 O1 -0.5(3) . . . . ?
C9 C10 C15 C14 -177.94(19) . . . . ?
C10 C9 N1 C7 -179.57(18) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C11 C10 C15 C14 0.7(3) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C12 C13 C14 C16 179.8(2) . . . . ?
C13 C14 C15 C10 -0.4(3) . . . . ?
C15 C10 C11 C12 -0.7(3) . . . . ?
C15 C10 C11 O1 -179.16(19) . . . . ?
C16 C14 C15 C10 179.83(19) . . . . ?
N1 C9 C10 C11 -0.3(3) . . . . ?
N1 C9 C10 C15 178.37(19) . . . . ?
O1 C11 C12 C13 178.8(2) . . . . ?
