#------------------------------------------------------------------------------
#$Date: 2020-06-06 04:11:42 +0300 (Sat, 06 Jun 2020) $
#$Revision: 252959 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558206.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_1558206
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            'C18 H15.01 N2 O2'
_chemical_formula_weight         291.33
_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             2020-04-01T17:45:53-00:00
_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                92.4784(16)
_cell_angle_beta                 107.8241(12)
_cell_angle_gamma                114.4657(15)
_cell_formula_units_Z            2
_cell_length_a                   8.13837(14)
_cell_length_b                   9.8450(2)
_cell_length_c                   10.92312(12)
_cell_measurement_reflns_used    18331
_cell_measurement_temperature    210(2)
_cell_measurement_theta_max      76.206
_cell_measurement_theta_min      4.322
_cell_volume                     743.63(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.65a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.65a (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      210(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_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      -0.0032376
_diffrn_orient_matrix_UB_12      -0.0565981
_diffrn_orient_matrix_UB_13      0.1478999
_diffrn_orient_matrix_UB_21      -0.1510082
_diffrn_orient_matrix_UB_22      0.1527942
_diffrn_orient_matrix_UB_23      0.0270556
_diffrn_orient_matrix_UB_31      -0.1496497
_diffrn_orient_matrix_UB_32      -0.0647266
_diffrn_orient_matrix_UB_33      0.0148352
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            28285
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.217
_diffrn_reflns_theta_min         4.336
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.694
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.83548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.65a (Rigaku Oxford Diffraction, 2019)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_description       irregular
_exptl_crystal_F_000             306
_exptl_crystal_size_max          0.234
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.0049(7)
_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   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3085
_refine_ls_number_restraints     460
_refine_ls_restrained_S_all      0.99
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0332
_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)+(0.0462P)²+0.0924P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.0912
_reflns_Friedel_coverage         0
_reflns_number_gt                2850
_reflns_number_total             3085
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02795b3.cif
_cod_data_source_block           BE50_BA50_210
_cod_original_cell_volume        743.63(2)
_cod_database_code               1558206
_shelx_estimated_absorpt_t_min   0.888
_shelx_estimated_absorpt_t_max   0.956
_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 0.16705(10) 0.15041(8) 0.30484(7) 0.04387(19) Uani 1 1 d . . . . .
H1 H 0.2063(8) 0.1812(15) 0.3996(14) 0.066 Uiso 1 1 calc R U . . .
O2 O 0.82074(11) 0.22074(9) 0.43274(7) 0.0506(2) Uani 1 1 d . . . . .
H2A H 0.8263(7) 0.2633(16) 0.5170(15) 0.076 Uiso 1 1 calc R U . . .
N1 N 0.26269(12) 0.24405(10) -0.43205(8) 0.0451(2) Uani 1 1 d . . . . .
C1 C 0.31745(14) 0.14911(9) 0.27601(9) 0.0361(2) Uani 1 1 d . . . . .
C2 C 0.49352(13) 0.18438(10) 0.37336(8) 0.0363(2) Uani 1 1 d . . . . .
H2 H 0.510177 0.209016 0.46184 0.044 Uiso 1 1 calc R U . . .
C3 C 0.64537(14) 0.18345(10) 0.34065(9) 0.0391(2) Uani 1 1 d . . . . .
C4 C 0.61979(16) 0.14406(11) 0.20958(10) 0.0455(2) Uani 1 1 d . . . . .
H4 H 0.720975 0.141723 0.186585 0.055 Uiso 1 1 calc R U . . .
C5 C 0.44333(17) 0.10855(12) 0.11418(10) 0.0486(3) Uani 1 1 d . . . . .
H5 H 0.425732 0.082135 0.025769 0.058 Uiso 1 1 calc R U . . .
C6 C 0.29160(16) 0.11079(11) 0.14514(9) 0.0441(2) Uani 1 1 d . . . . .
H6 H 0.17283 0.086736 0.078654 0.053 Uiso 1 1 calc R U . . .
C7 C 0.19719(15) 0.14689(12) -0.35695(10) 0.0441(2) Uani 1 1 d . . . . .
H7 H 0.154771 0.042739 -0.386203 0.053 Uiso 1 1 calc R U . . .
C8 C 0.18877(14) 0.19182(11) -0.23887(10) 0.0416(2) Uani 1 1 d . . . . .
H8 H 0.140499 0.119174 -0.189723 0.05 Uiso 1 1 calc R U . . .
C9 C 0.25210(13) 0.34530(11) -0.19268(9) 0.0382(2) Uani 1 1 d D U . . .
C10 C 0.32581(15) 0.44735(11) -0.26849(10) 0.0446(2) Uani 1 1 d . . . . .
H10 H 0.374461 0.552544 -0.239885 0.053 Uiso 1 1 calc R U . . .
C11 C 0.32642(15) 0.39191(12) -0.38609(10) 0.0470(2) Uani 1 1 d . . . . .
H11 H 0.374435 0.462003 -0.437169 0.056 Uiso 1 1 calc R U . . .
C12 C 0.2203(11) 0.3800(6) -0.0660(6) 0.0318(8) Uani 0.506(10) 1 d D U P A 1
H12 H 0.165597 0.298722 -0.025976 0.038 Uiso 0.506(10) 1 calc R U P A 1
C13 C 0.2661(4) 0.5185(5) -0.0109(3) 0.0317(7) Uani 0.506(10) 1 d D U P A 1
H13 H 0.326138 0.598222 -0.050548 0.038 Uiso 0.506(10) 1 calc R U P A 1
C14A C 0.2314(11) 0.5620(7) 0.1106(5) 0.0299(10) Uani 0.506(10) 1 d G U P A 1
C15A C 0.1488(12) 0.4535(6) 0.1789(7) 0.0369(11) Uani 0.506(10) 1 d G U P A 1
H15A H 0.113263 0.350514 0.150276 0.044 Uiso 0.506(10) 1 calc R U P A 1
C16A C 0.1187(12) 0.4972(7) 0.2897(7) 0.0382(13) Uani 0.506(10) 1 d G U P A 1
H16A H 0.062834 0.423865 0.33589 0.046 Uiso 0.506(10) 1 calc R U P A 1
N2A N 0.1713(12) 0.6495(8) 0.3321(6) 0.0356(13) Uani 0.506(10) 1 d G U P A 1
C17A C 0.2539(12) 0.7580(6) 0.2637(6) 0.0354(11) Uani 0.506(10) 1 d G U P A 1
H17A H 0.289461 0.860983 0.292373 0.043 Uiso 0.506(10) 1 calc R U P A 1
C18A C 0.2840(11) 0.7143(6) 0.1530(6) 0.0346(10) Uani 0.506(10) 1 d G U P A 1
H18A H 0.339891 0.787636 0.106759 0.041 Uiso 0.506(10) 1 calc R U P A 1
C14B C 0.2164(13) 0.5269(9) 0.1213(6) 0.0391(13) Uani 0.494(10) 1 d . U P A 2
C15B C 0.1277(14) 0.4432(7) 0.2017(8) 0.0437(12) Uani 0.494(10) 1 d . U P A 2
H15B H 0.078375 0.33674 0.186488 0.052 Uiso 0.494(10) 1 calc R U P A 2
C16B C 0.1131(14) 0.5182(9) 0.3034(8) 0.0424(12) Uani 0.494(10) 1 d . U P A 2
H16B H 0.05071 0.457267 0.354829 0.051 Uiso 0.494(10) 1 calc R U P A 2
N2B N 0.1753(14) 0.6628(10) 0.3366(7) 0.0477(16) Uani 0.494(10) 1 d . U P A 2
C17B C 0.2574(14) 0.7373(9) 0.2606(8) 0.0455(13) Uani 0.494(10) 1 d . U P A 2
H17B H 0.307143 0.843678 0.281297 0.055 Uiso 0.494(10) 1 calc R U P A 2
C18B C 0.2814(12) 0.6823(8) 0.1543(7) 0.0388(11) Uani 0.494(10) 1 d . U P A 2
H18B H 0.340712 0.748301 0.104432 0.047 Uiso 0.494(10) 1 calc R U P A 2
C19 C 0.2500(12) 0.4114(9) -0.0804(8) 0.0461(13) Uani 0.494(10) 1 d D U P A 2
C20 C 0.2353(6) 0.4634(8) 0.0145(4) 0.0467(9) Uani 0.494(10) 1 d D U P A 2
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
1 0 2 0.1024
1 -5 -4 0.0508
-4 -6 -4 0.0654
2 6 4 0.0464
4 6 1 0.0435
1 2 7 0.0957
1 6 -1 0.0561
2 -2 -5 0.054
1 -5 0 0.0733
0 6 2 0.0367
-4 2 1 0.0427
-1 -6 1 0.0835
3 2 -4 0.0582
5 4 -1 0.0444
5 5 4 0.0804
-5 -4 -3 0.0658
-5 -2 0 0.0435
2 -4 2 0.0954
-4 -5 0 0.0468
-1 4 4 0.0337
2 6 3 0.0426
-2 -6 -3 0.0582
4 5 0 0.0438
2 0 -6 0.081
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 . . ?
C7 N1 C11 116.90(8) . . ?
O1 C1 C2 121.69(8) . . ?
O1 C1 C6 118.35(9) . . ?
C2 C1 C6 119.96(9) . . ?
C1 C2 C3 120.35(8) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
O2 C3 C2 122.03(8) . . ?
O2 C3 C4 118.05(9) . . ?
C2 C3 C4 119.92(9) . . ?
C5 C4 C3 118.89(10) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 121.83(9) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 119.04(9) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N1 C7 C8 123.22(9) . . ?
N1 C7 H7 118.4 . . ?
C8 C7 H7 118.4 . . ?
C7 C8 C9 119.61(9) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C19 C9 C10 114.4(3) . . ?
C19 C9 C8 128.2(3) . . ?
C10 C9 C8 117.41(9) . . ?
C10 C9 C12 127.7(2) . . ?
C8 C9 C12 114.8(2) . . ?
C11 C10 C9 118.93(9) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N1 C11 C10 123.87(9) . . ?
N1 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C13 C12 C9 122.9(5) . . ?
C13 C12 H12 118.6 . . ?
C9 C12 H12 118.6 . . ?
C12 C13 C14A 126.3(5) . . ?
C12 C13 H13 116.9 . . ?
C14A C13 H13 116.9 . . ?
C15A C14A C18A 120 . . ?
C15A C14A C13 121.5(3) . . ?
C18A C14A C13 118.5(3) . . ?
C14A C15A C16A 120 . . ?
C14A C15A H15A 120 . . ?
C16A C15A H15A 120 . . ?
C15A C16A N2A 120 . . ?
C15A C16A H16A 120 . . ?
N2A C16A H16A 120 . . ?
C17A N2A C16A 120 . . ?
N2A C17A C18A 120 . . ?
N2A C17A H17A 120 . . ?
C18A C17A H17A 120 . . ?
C17A C18A C14A 120 . . ?
C17A C18A H18A 120 . . ?
C14A C18A H18A 120 . . ?
C20 C14B C18B 121.5(5) . . ?
C20 C14B C15B 124.1(4) . . ?
C18B C14B C15B 114.4(3) . . ?
C16B C15B C14B 119.1(3) . . ?
C16B C15B H15B 120.5 . . ?
C14B C15B H15B 120.5 . . ?
N2B C16B C15B 127.3(4) . . ?
N2B C16B H16B 116.4 . . ?
C15B C16B H16B 116.4 . . ?
C17B N2B C16B 112.3(4) . . ?
N2B C17B C18B 128.5(4) . . ?
N2B C17B H17B 115.7 . . ?
C18B C17B H17B 115.7 . . ?
C17B C18B C14B 118.5(3) . . ?
C17B C18B H18B 120.8 . . ?
C14B C18B H18B 120.8 . . ?
C20 C19 C9 175.7(8) . . ?
C19 C20 C14B 178.0(8) . . ?
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 1.3587(12) . ?
O1 H1 0.977(15) . ?
O2 C3 1.3560(12) . ?
O2 H2A 0.975(16) . ?
N1 C7 1.3362(14) . ?
N1 C11 1.3387(14) . ?
C1 C2 1.3884(13) . ?
C1 C6 1.3905(13) . ?
C2 C3 1.3908(13) . ?
C2 H2 0.94 . ?
C3 C4 1.3950(13) . ?
C4 C5 1.3809(16) . ?
C4 H4 0.94 . ?
C5 C6 1.3846(15) . ?
C5 H5 0.94 . ?
C6 H6 0.94 . ?
C7 C8 1.3761(14) . ?
C7 H7 0.94 . ?
C8 C9 1.3904(13) . ?
C8 H8 0.94 . ?
C9 C19 1.371(8) . ?
C9 C10 1.3899(14) . ?
C9 C12 1.533(6) . ?
C10 C11 1.3761(15) . ?
C10 H10 0.94 . ?
C11 H11 0.94 . ?
C12 C13 1.316(7) . ?
C12 H12 0.94 . ?
C13 C14A 1.518(5) . ?
C13 H13 0.94 . ?
C14A C15A 1.39 . ?
C14A C18A 1.39 . ?
C15A C16A 1.39 . ?
C15A H15A 0.94 . ?
C16A N2A 1.39 . ?
C16A H16A 0.94 . ?
N2A C17A 1.39 . ?
C17A C18A 1.39 . ?
C17A H17A 0.94 . ?
C18A H18A 0.94 . ?
C14B C20 1.379(6) . ?
C14B C18B 1.384(5) . ?
C14B C15B 1.389(6) . ?
C15B C16B 1.370(5) . ?
C15B H15B 0.94 . ?
C16B N2B 1.289(5) . ?
C16B H16B 0.94 . ?
N2B C17B 1.288(5) . ?
C17B C18B 1.361(4) . ?
C17B H17B 0.94 . ?
C18B H18B 0.94 . ?
C19 C20 1.196(8) . ?
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 0.98 1.77 2.7427(11) 174.9 1_556 yes
O2 H2A N2A^a 0.97 1.82 2.79(3) 176 2_666 yes
O2 H2A N2B^b 0.97 1.73 2.708(6) 177.3 2_666 yes
