#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:11:42 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558228.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_1558228
loop_
_publ_author_name
'Ding, Xiaodan'
'Unruh, Daniel K.'
'Groeneman , Ryan'
'Hutchins, Kristin M.'
_publ_section_title
;
 Controlling thermal expansion within mixed cocrystals by tuning molecular
 motion capability
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02795B
_journal_year                    2020
_chemical_formula_sum            'C16.51 H14 N3.49 O2'
_chemical_formula_weight         293.36
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-11-07T15:21:52-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2020-04-08 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                93.4267(17)
_cell_angle_beta                 106.8463(19)
_cell_angle_gamma                113.829(2)
_cell_formula_units_Z            2
_cell_length_a                   8.03328(18)
_cell_length_b                   9.7401(2)
_cell_length_c                   10.8685(2)
_cell_measurement_reflns_used    6099
_cell_measurement_temperature    230(2)
_cell_measurement_theta_max      74.563
_cell_measurement_theta_min      4.326
_cell_volume                     729.18(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      230(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0242743
_diffrn_orient_matrix_UB_12      -0.1049263
_diffrn_orient_matrix_UB_13      0.1005706
_diffrn_orient_matrix_UB_21      -0.1947038
_diffrn_orient_matrix_UB_22      -0.1187566
_diffrn_orient_matrix_UB_23      -0.1004155
_diffrn_orient_matrix_UB_31      0.1065049
_diffrn_orient_matrix_UB_32      -0.0778151
_diffrn_orient_matrix_UB_33      -0.0516645
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12806
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.357
_diffrn_reflns_theta_min         4.34
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.742
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.722
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       plate
_exptl_crystal_F_000             307
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0050(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         2949
_refine_ls_number_restraints     507
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0453
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0749P)²+0.0927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1357
_reflns_Friedel_coverage         0
_reflns_number_gt                2433
_reflns_number_total             2949
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b3.cif
_cod_data_source_block           A75_BA25_230
_cod_original_cell_volume        729.19(3)
_cod_database_code               1558228
_shelx_estimated_absorpt_t_min   0.862
_shelx_estimated_absorpt_t_max   0.981
_shelx_shelxl_version_number     2018/3
loop_
_symmetry_equiv_pos_as_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
O1 O 0.16619(15) 0.15638(12) 0.31178(10) 0.0545(3) Uani 1 1 d . . . . .
H1 H 0.196309 0.176599 0.392741 0.082 Uiso 1 1 calc R U . . .
O2 O 0.82089(16) 0.21815(15) 0.43527(11) 0.0636(3) Uani 1 1 d . . . . .
H2A H 0.824619 0.254046 0.507769 0.095 Uiso 1 1 calc R U . . .
N1 N 0.26157(18) 0.24836(15) -0.42102(13) 0.0538(3) Uani 1 1 d . . . . .
C1 C 0.3176(2) 0.15302(15) 0.28155(13) 0.0445(3) Uani 1 1 d . . . . .
C2 C 0.4927(2) 0.18507(15) 0.37816(13) 0.0455(3) Uani 1 1 d . . . . .
H2 H 0.508181 0.208643 0.467125 0.055 Uiso 1 1 calc R U . . .
C3 C 0.6450(2) 0.18237(16) 0.34359(14) 0.0483(3) Uani 1 1 d . . . . .
C4 C 0.6209(2) 0.14335(18) 0.21265(15) 0.0550(4) Uani 1 1 d . . . . .
H4 H 0.722184 0.138545 0.188692 0.066 Uiso 1 1 calc R U . . .
C5 C 0.4451(3) 0.11161(17) 0.11785(15) 0.0567(4) Uani 1 1 d . . . . .
H5 H 0.428778 0.086312 0.028945 0.068 Uiso 1 1 calc R U . . .
C6 C 0.2931(2) 0.11607(17) 0.15024(14) 0.0526(4) Uani 1 1 d . . . . .
H6 H 0.17499 0.094413 0.084386 0.063 Uiso 1 1 calc R U . . .
C7 C 0.3265(2) 0.39751(19) -0.37244(17) 0.0593(4) Uani 1 1 d . . . . .
H7 H 0.376644 0.468727 -0.422365 0.071 Uiso 1 1 calc R U . . .
C8 C 0.3240(2) 0.45224(18) -0.25363(17) 0.0578(4) Uani 1 1 d . . . . .
H8 H 0.372914 0.557953 -0.222474 0.069 Uiso 1 1 calc R U . . .
C9 C 0.2473(2) 0.34698(17) -0.18149(15) 0.0496(4) Uani 1 1 d D . . . .
C10 C 0.1828(2) 0.19292(17) -0.22904(15) 0.0509(4) Uani 1 1 d . . . . .
H10 H 0.132713 0.119364 -0.18085 0.061 Uiso 1 1 calc R U . . .
C11 C 0.1933(2) 0.14946(17) -0.34784(15) 0.0522(4) Uani 1 1 d . . . . .
H11 H 0.150172 0.044618 -0.379321 0.063 Uiso 1 1 calc R U . . .
N2A N 0.2115(8) 0.3762(5) -0.0573(4) 0.0433(10) Uani 0.667(13) 1 d D U P A 1
N3A N 0.2662(5) 0.5145(5) -0.0166(4) 0.0448(9) Uani 0.667(13) 1 d D U P A 1
C12A C 0.2324(9) 0.5544(6) 0.1001(5) 0.0387(9) Uani 0.667(13) 1 d . U P A 1
C13A C 0.2868(11) 0.7072(6) 0.1462(6) 0.0481(10) Uani 0.667(13) 1 d . U P A 1
H13A H 0.34474 0.783554 0.102691 0.058 Uiso 0.667(13) 1 calc R U P A 1
C14A C 0.2526(13) 0.7436(6) 0.2592(7) 0.0522(15) Uani 0.667(13) 1 d . U P A 1
H14A H 0.290011 0.847475 0.290428 0.063 Uiso 0.667(13) 1 calc R U P A 1
N4A N 0.1725(12) 0.6449(8) 0.3253(6) 0.0478(11) Uani 0.667(13) 1 d . U P A 1
C15A C 0.1204(10) 0.4994(7) 0.2787(6) 0.0467(10) Uani 0.667(13) 1 d . U P A 1
H15A H 0.060796 0.426228 0.324097 0.056 Uiso 0.667(13) 1 calc R U P A 1
C16A C 0.1469(8) 0.4475(5) 0.1688(5) 0.0428(10) Uani 0.667(13) 1 d . U P A 1
H16A H 0.108258 0.342653 0.140955 0.051 Uiso 0.667(13) 1 calc R U P A 1
C12B C 0.2093(18) 0.5197(12) 0.1218(9) 0.041(2) Uani 0.333(13) 1 d DG U P A 2
C13B C 0.280(2) 0.6782(12) 0.1462(12) 0.053(2) Uani 0.333(13) 1 d G U P A 2
H13B H 0.338175 0.735178 0.090677 0.063 Uiso 0.333(13) 1 calc R U P A 2
C14B C 0.265(3) 0.7526(10) 0.2527(15) 0.055(3) Uani 0.333(13) 1 d G U P A 2
H14B H 0.312662 0.859763 0.269192 0.066 Uiso 0.333(13) 1 calc R U P A 2
N4B N 0.179(3) 0.6684(15) 0.3348(13) 0.056(3) Uani 0.333(13) 1 d G U P A 2
C15B C 0.1081(19) 0.5098(15) 0.3103(11) 0.052(2) Uani 0.333(13) 1 d G U P A 2
H15B H 0.050024 0.452895 0.365852 0.062 Uiso 0.333(13) 1 calc R U P A 2
C16B C 0.1234(16) 0.4355(10) 0.2038(11) 0.050(2) Uani 0.333(13) 1 d G U P A 2
H16B H 0.075535 0.328307 0.187337 0.06 Uiso 0.333(13) 1 calc R U P A 2
C17 C 0.2333(18) 0.463(2) 0.0191(11) 0.050(3) Uani 0.257(15) 1 d D U P A 2
C18 C 0.254(2) 0.415(2) -0.0753(13) 0.049(3) Uani 0.257(15) 1 d D U P A 2
N2B N 0.291(4) 0.486(4) -0.060(3) 0.056(5) Uani 0.079(7) 1 d D U P A 3
N3B N 0.185(4) 0.394(3) -0.010(3) 0.050(5) Uani 0.079(7) 1 d D U P A 3
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 4 3 0.1092
4 0 0 0.0687
0 5 -5 0.001
-2 5 4 0.0741
3 -5 -4 0.107
-4 0 0 0.0879
3 3 -3 0.045
0 -5 5 0.0227
4 -4 -4 0.116
0 -4 -4 0.1248
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
C1 O1 H1 109.5 . . ?
C3 O2 H2A 109.5 . . ?
C11 N1 C7 117.14(14) . . ?
O1 C1 C6 118.16(13) . . ?
O1 C1 C2 121.70(12) . . ?
C6 C1 C2 120.14(13) . . ?
C1 C2 C3 120.13(13) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
O2 C3 C4 118.04(14) . . ?
O2 C3 C2 121.83(13) . . ?
C4 C3 C2 120.13(14) . . ?
C5 C4 C3 118.81(15) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C6 C5 C4 121.86(14) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 118.90(14) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.71(15) . . ?
N1 C7 H7 118.1 . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 117.97(14) . . ?
C7 C8 H8 121 . . ?
C9 C8 H8 121 . . ?
C18 C9 C8 110.3(10) . . ?
C18 C9 C10 130.6(10) . . ?
C8 C9 C10 119.07(14) . . ?
C8 C9 N2A 128.0(2) . . ?
C10 C9 N2A 112.8(2) . . ?
C8 C9 N2B 92.2(8) . . ?
C10 C9 N2B 148.7(8) . . ?
C11 C10 C9 118.73(14) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
N1 C11 C10 123.35(14) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
N3A N2A C9 112.5(6) . . ?
N2A N3A C12A 116.9(6) . . ?
C13A C12A C16A 118.2(3) . . ?
C13A C12A N3A 118.4(4) . . ?
C16A C12A N3A 123.4(3) . . ?
C12A C13A C14A 117.6(3) . . ?
C12A C13A H13A 121.2 . . ?
C14A C13A H13A 121.2 . . ?
N4A C14A C13A 125.2(3) . . ?
N4A C14A H14A 117.4 . . ?
C13A C14A H14A 117.4 . . ?
C14A N4A C15A 116.2(3) . . ?
N4A C15A C16A 124.8(3) . . ?
N4A C15A H15A 117.6 . . ?
C16A C15A H15A 117.6 . . ?
C15A C16A C12A 118.1(3) . . ?
C15A C16A H16A 120.9 . . ?
C12A C16A H16A 120.9 . . ?
C17 C12B C13B 114.4(9) . . ?
C17 C12B C16B 125.6(9) . . ?
C13B C12B C16B 120 . . ?
C12B C13B C14B 120 . . ?
C12B C13B H13B 120 . . ?
C14B C13B H13B 120 . . ?
N4B C14B C13B 120 . . ?
N4B C14B H14B 120 . . ?
C13B C14B H14B 120 . . ?
C15B N4B C14B 120 . . ?
C16B C15B N4B 120 . . ?
C16B C15B H15B 120 . . ?
N4B C15B H15B 120 . . ?
C15B C16B C12B 120 . . ?
C15B C16B H16B 120 . . ?
C12B C16B H16B 120 . . ?
C18 C17 C12B 178(2) . . ?
C17 C18 C9 170(2) . . ?
N3B N2B C9 93(4) . . ?
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
O1 C1 1.3602(18) . ?
O1 H1 0.83 . ?
O2 C3 1.3624(18) . ?
O2 H2A 0.83 . ?
N1 C11 1.334(2) . ?
N1 C7 1.341(2) . ?
C1 C6 1.387(2) . ?
C1 C2 1.389(2) . ?
C2 C3 1.389(2) . ?
C2 H2 0.94 . ?
C3 C4 1.387(2) . ?
C4 C5 1.385(2) . ?
C4 H4 0.94 . ?
C5 C6 1.381(2) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.376(2) . ?
C7 H7 0.94 . ?
C8 C9 1.382(2) . ?
C8 H8 0.94 . ?
C9 C18 1.274(12) . ?
C9 C10 1.382(2) . ?
C9 N2A 1.493(5) . ?
C9 N2B 1.68(4) . ?
C10 C11 1.371(2) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
N2A N3A 1.241(6) . ?
N3A C12A 1.435(6) . ?
C12A C13A 1.384(4) . ?
C12A C16A 1.387(4) . ?
C13A C14A 1.389(4) . ?
C13A H13A 0.94 . ?
C14A N4A 1.306(5) . ?
C14A H14A 0.94 . ?
N4A C15A 1.323(5) . ?
C15A C16A 1.376(5) . ?
C15A H15A 0.94 . ?
C16A H16A 0.94 . ?
C12B C17 1.314(11) . ?
C12B C13B 1.39 . ?
C12B C16B 1.39 . ?
C13B C14B 1.39 . ?
C13B H13B 0.94 . ?
C14B N4B 1.39 . ?
C14B H14B 0.94 . ?
N4B C15B 1.39 . ?
C15B C16B 1.39 . ?
C15B H15B 0.94 . ?
C16B H16B 0.94 . ?
C17 C18 1.182(16) . ?
N2B N3B 1.24(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.83 1.94 2.7691(16) 172.3 1_556 yes
O2 H2A N4A 0.83 2 2.829(5) 174.7 2_666 yes
O2 H2A N4B 0.83 1.84 2.67(6) 177.4 2_666 yes
