#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:11:42 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558227.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_1558227
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            'C16.47 H14 N3.52 O2'
_chemical_formula_weight         293.21
_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             2019-11-07T15:25:03-00:00
_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                93.754(3)
_cell_angle_beta                 106.789(3)
_cell_angle_gamma                113.675(4)
_cell_formula_units_Z            2
_cell_length_a                   8.0903(3)
_cell_length_b                   9.7624(3)
_cell_length_c                   10.8911(3)
_cell_measurement_reflns_used    5180
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      73.76
_cell_measurement_theta_min      4.341
_cell_volume                     737.88(5)
_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      air
_diffrn_ambient_temperature      290(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.953
_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      -0.0450258
_diffrn_orient_matrix_UB_12      -0.1162217
_diffrn_orient_matrix_UB_13      0.0889076
_diffrn_orient_matrix_UB_21      -0.1889378
_diffrn_orient_matrix_UB_22      -0.1070355
_diffrn_orient_matrix_UB_23      -0.1109451
_diffrn_orient_matrix_UB_31      0.1064899
_diffrn_orient_matrix_UB_32      -0.0778108
_diffrn_orient_matrix_UB_33      -0.0509262
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.953
_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       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12567
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.337
_diffrn_reflns_theta_min         4.334
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.648
_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    1.32
_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         0.209
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.010(2)
_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   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         2993
_refine_ls_number_restraints     507
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0542
_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)+(0.0999P)²+0.0683P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.151
_refine_ls_wR_factor_ref         0.179
_reflns_Friedel_coverage         0
_reflns_number_gt                2273
_reflns_number_total             2993
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b3.cif
_cod_data_source_block           A75_BA25_290
_cod_database_code               1558227
_shelx_estimated_absorpt_t_min   0.864
_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 0.16732(19) 0.15326(16) 0.31212(12) 0.0718(4) Uani 1 1 d . . . . .
H1 H 0.197958 0.176011 0.391933 0.108 Uiso 1 1 calc R U . . .
O2 O 0.8176(2) 0.21713(19) 0.43456(14) 0.0847(5) Uani 1 1 d . . . . .
H2A H 0.822719 0.255613 0.505617 0.127 Uiso 1 1 calc R U . . .
N1 N 0.2611(2) 0.24742(19) -0.42110(16) 0.0703(4) Uani 1 1 d . . . . .
C1 C 0.3183(3) 0.15069(18) 0.28186(16) 0.0586(4) Uani 1 1 d . . . . .
C2 C 0.4918(3) 0.18304(19) 0.37804(16) 0.0598(4) Uani 1 1 d . . . . .
H2 H 0.506788 0.206031 0.465949 0.072 Uiso 1 1 calc R U . . .
C3 C 0.6438(3) 0.1813(2) 0.34365(17) 0.0632(5) Uani 1 1 d . . . . .
C4 C 0.6196(3) 0.1424(2) 0.21297(19) 0.0714(5) Uani 1 1 d . . . . .
H4 H 0.718918 0.137624 0.189073 0.086 Uiso 1 1 calc R U . . .
C5 C 0.4453(3) 0.1108(2) 0.11856(18) 0.0751(6) Uani 1 1 d . . . . .
H5 H 0.429496 0.086538 0.030626 0.09 Uiso 1 1 calc R U . . .
C6 C 0.2942(3) 0.1141(2) 0.15106(18) 0.0690(5) Uani 1 1 d . . . . .
H6 H 0.177977 0.092083 0.086064 0.083 Uiso 1 1 calc R U . . .
C7 C 0.3268(3) 0.3963(2) -0.3738(2) 0.0761(5) Uani 1 1 d . . . . .
H7 H 0.376306 0.465469 -0.423468 0.091 Uiso 1 1 calc R U . . .
C8 C 0.3251(3) 0.4526(2) -0.2552(2) 0.0752(5) Uani 1 1 d . . . . .
H8 H 0.373674 0.55717 -0.224899 0.09 Uiso 1 1 calc R U . . .
C9 C 0.2496(3) 0.3499(2) -0.18279(18) 0.0652(5) Uani 1 1 d D . . . .
C10 C 0.1844(3) 0.1963(2) -0.22957(18) 0.0684(5) Uani 1 1 d . . . . .
H10 H 0.135209 0.124877 -0.181441 0.082 Uiso 1 1 calc R U . . .
C11 C 0.1932(3) 0.1507(2) -0.34736(19) 0.0696(5) Uani 1 1 d . . . . .
H11 H 0.149504 0.046805 -0.377951 0.083 Uiso 1 1 calc R U . . .
N2A N 0.2127(10) 0.3784(6) -0.0576(6) 0.0576(14) Uani 0.608(14) 1 d D U P A 1
N3A N 0.2655(7) 0.5136(6) -0.0161(6) 0.0607(12) Uani 0.608(14) 1 d D U P A 1
C12A C 0.2331(12) 0.5534(8) 0.1018(7) 0.0525(11) Uani 0.608(14) 1 d . U P A 1
C13A C 0.2841(15) 0.7055(8) 0.1484(8) 0.0643(13) Uani 0.608(14) 1 d . U P A 1
H13A H 0.340707 0.781332 0.106069 0.077 Uiso 0.608(14) 1 calc R U P A 1
C14A C 0.2481(16) 0.7408(7) 0.2600(9) 0.0669(17) Uani 0.608(14) 1 d . U P A 1
H14A H 0.282835 0.843107 0.290779 0.08 Uiso 0.608(14) 1 calc R U P A 1
N4A N 0.1699(15) 0.6431(10) 0.3251(8) 0.0647(16) Uani 0.608(14) 1 d . U P A 1
C15A C 0.1217(14) 0.5001(10) 0.2781(8) 0.0642(13) Uani 0.608(14) 1 d . U P A 1
H15A H 0.064095 0.427351 0.32257 0.077 Uiso 0.608(14) 1 calc R U P A 1
C16A C 0.1492(11) 0.4486(7) 0.1686(7) 0.0593(14) Uani 0.608(14) 1 d . U P A 1
H16A H 0.111685 0.345125 0.140746 0.071 Uiso 0.608(14) 1 calc R U P A 1
C12B C 0.2048(19) 0.5127(13) 0.1161(10) 0.059(2) Uani 0.392(14) 1 d DG U P A 2
C13B C 0.280(2) 0.6713(13) 0.1424(12) 0.068(3) Uani 0.392(14) 1 d G U P A 2
H13B H 0.337488 0.726677 0.087467 0.082 Uiso 0.392(14) 1 calc R U P A 2
C14B C 0.270(2) 0.7470(11) 0.2507(14) 0.073(3) Uani 0.392(14) 1 d G U P A 2
H14B H 0.321031 0.853035 0.268275 0.087 Uiso 0.392(14) 1 calc R U P A 2
N4B N 0.185(2) 0.6641(16) 0.3327(12) 0.071(3) Uani 0.392(14) 1 d G U P A 2
C15B C 0.110(2) 0.5056(15) 0.3064(12) 0.067(2) Uani 0.392(14) 1 d G U P A 2
H15B H 0.052458 0.450183 0.361341 0.08 Uiso 0.392(14) 1 calc R U P A 2
C16B C 0.1194(18) 0.4299(11) 0.1981(12) 0.062(2) Uani 0.392(14) 1 d G U P A 2
H16B H 0.068914 0.323821 0.180534 0.075 Uiso 0.392(14) 1 calc R U P A 2
C17 C 0.234(3) 0.461(4) 0.0185(15) 0.064(3) Uani 0.234(17) 1 d D U P A 2
C18 C 0.255(4) 0.414(4) -0.0775(18) 0.063(4) Uani 0.234(17) 1 d D U P A 2
N2B N 0.280(3) 0.477(3) -0.069(2) 0.061(3) Uani 0.152(10) 1 d D U P A 3
N3B N 0.189(3) 0.395(4) -0.005(3) 0.065(4) Uani 0.152(10) 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
5 -4 -4 0.116
-2 4 5 0.0741
0 5 -5 0.001
3 3 -3 0.045
4 -1 1 0.0687
0 -5 5 0.0227
-4 1 -1 0.0879
0 -4 -4 0.1248
3 -5 -4 0.107
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 117.22(17) . . ?
O1 C1 C6 118.10(16) . . ?
O1 C1 C2 121.76(15) . . ?
C6 C1 C2 120.15(17) . . ?
C1 C2 C3 120.26(16) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
O2 C3 C4 118.13(17) . . ?
O2 C3 C2 122.02(16) . . ?
C4 C3 C2 119.85(18) . . ?
C5 C4 C3 118.89(18) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C6 C5 C4 121.89(17) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C1 118.93(18) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.3(2) . . ?
N1 C7 H7 118.3 . . ?
C8 C7 H7 118.3 . . ?
C9 C8 C7 118.18(18) . . ?
C9 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
C18 C9 C8 112.5(16) . . ?
C18 C9 C10 128.4(16) . . ?
C8 C9 C10 119.00(18) . . ?
C8 C9 N2A 129.2(3) . . ?
C10 C9 N2A 111.7(3) . . ?
C8 C9 N2B 94.3(6) . . ?
C10 C9 N2B 146.7(6) . . ?
C11 C10 C9 118.91(19) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N1 C11 C10 123.33(18) . . ?
N1 C11 H11 118.3 . . ?
C10 C11 H11 118.3 . . ?
N3A N2A C9 112.7(8) . . ?
N2A N3A C12A 117.3(8) . . ?
C16A C12A C13A 117.7(4) . . ?
C16A C12A N3A 123.5(5) . . ?
C13A C12A N3A 118.7(5) . . ?
C14A C13A C12A 117.8(4) . . ?
C14A C13A H13A 121.1 . . ?
C12A C13A H13A 121.1 . . ?
N4A C14A C13A 125.3(4) . . ?
N4A C14A H14A 117.3 . . ?
C13A C14A H14A 117.3 . . ?
C14A N4A C15A 115.5(4) . . ?
N4A C15A C16A 125.4(5) . . ?
N4A C15A H15A 117.3 . . ?
C16A C15A H15A 117.3 . . ?
C12A C16A C15A 118.2(4) . . ?
C12A C16A H16A 120.9 . . ?
C15A C16A H16A 120.9 . . ?
C17 C12B C13B 112.5(14) . . ?
C17 C12B C16B 127.4(14) . . ?
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 . . ?
C14B N4B C15B 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 177(2) . . ?
C17 C18 C9 171(4) . . ?
N3B N2B C9 100(3) . . ?
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 1.363(2) . ?
O1 H1 0.82 . ?
O2 C3 1.354(2) . ?
O2 H2A 0.82 . ?
N1 C11 1.333(3) . ?
N1 C7 1.336(3) . ?
C1 C6 1.383(2) . ?
C1 C2 1.385(2) . ?
C2 C3 1.390(3) . ?
C2 H2 0.93 . ?
C3 C4 1.384(3) . ?
C4 C5 1.383(3) . ?
C4 H4 0.93 . ?
C5 C6 1.378(3) . ?
C5 H5 0.93 . ?
C6 H6 0.93 . ?
C7 C8 1.376(3) . ?
C7 H7 0.93 . ?
C8 C9 1.375(3) . ?
C8 H8 0.93 . ?
C9 C18 1.249(14) . ?
C9 C10 1.377(3) . ?
C9 N2A 1.509(7) . ?
C9 N2B 1.58(3) . ?
C10 C11 1.361(3) . ?
C10 H10 0.93 . ?
C11 H11 0.93 . ?
N2A N3A 1.219(7) . ?
N3A C12A 1.442(9) . ?
C12A C16A 1.364(6) . ?
C12A C13A 1.386(6) . ?
C13A C14A 1.382(7) . ?
C13A H13A 0.93 . ?
C14A N4A 1.295(6) . ?
C14A H14A 0.93 . ?
N4A C15A 1.311(6) . ?
C15A C16A 1.375(7) . ?
C15A H15A 0.93 . ?
C16A H16A 0.93 . ?
C12B C17 1.268(13) . ?
C12B C13B 1.39 . ?
C12B C16B 1.39 . ?
C13B C14B 1.39 . ?
C13B H13B 0.93 . ?
C14B N4B 1.39 . ?
C14B H14B 0.93 . ?
N4B C15B 1.39 . ?
C15B C16B 1.39 . ?
C15B H15B 0.93 . ?
C16B H16B 0.93 . ?
C17 C18 1.201(18) . ?
N2B N3B 1.254(18) . ?
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 0.82 1.95 2.771(2) 173.7 1_556 yes
O2 H2A N4A 0.82 2.01 2.827(6) 177 2_666 yes
O2 H2A N4B 0.82 1.91 2.73(6) 175.8 2_666 yes
